Sergey A. Shlykov#, Tran D. Phien#, Yan Gao$ and Peter M. Weber$
Molecular structure and conformational properties of N-cyclohexylpiperidine as studied by gas-phase electron diffraction, mass spectrometry, IR spectroscopy and quantum chemical calculations
Sergey A. Shlykov#, Tran D. Phien#, Yan Gao$ and Peter M. Weber$
# Ivanovo State University of Chemistry and Technology, Research Institute for Thermodynamics and Kinetics of Chemical Processes, Department of Physical Chemistry, Sheremetev ave, 7, 153000, Ivanovo, Russian Federation
$Department of Chemistry, Brown University, Providence, Rhode Island 02912, United States
Cartesian coordinates (Å) and absolute energies (a.u.) of computed structures. The structures were confirmed to be minima through vibrational analysis.……………………..3
Experimental section…………………………………………………………………………...12
Table S1 Conditions of the synchronous GED/MS experiments……………………………….13
Mass-spectrometric……………………………………………………………………………..14
QST3calculations...…………………………………………………….………………………15
Table S2 Relative total electron and free Gibbs energies of the all possible conformers of molecule NCHP ……………………….……………………….………………………………..16
Table S3 Lowest vibrational frequencies of the conformers I, II and III (cm–1)……………....16
Table S4a Theoretical and experimental geometric parameters of conformer I………………..17
Table S4b Theoretical and experimental geometric parameters of conformer II……………….18
Table S4c Theoretical and experimental geometric parameters of conformer III……………....19
Table S5a Theoretical geometric parameters of conformer IV, V and VI……………………...21
Table S5b Theoretical geometric parameters of conformer VII and VIII……………………...22
Table S6Theoretical (MP2/6-311G**) and experimental (GED) root-mean square vibration amplitudes l and theoretical vibration corrections ∆r, Å without those for nonbonded distances involving hydrogen atoms……………………….……………………….……………………...23
Experimental scattering intensities and backgrounds……………………………………….30
Cartesian coordinates (Å) and absolute energies (a.u.) of computed structures. The structures were confirmed to be minima through vibrational analysis.
B3LYP/cc-pVTZ
Conformer IEqC-EqN-orth
E(RB3LYP) = –486.748613138
7 -0.753652000 0.056791000 0.327579000
6 -1.544164000 -1.140266000 0.595320000
6 -3.006276000 -0.782926000 0.860941000
6 -3.594193000 0.017823000 -0.302624000
6 -2.700785000 1.215456000 -0.629069000
6 -1.252743000 0.774568000 -0.842462000
6 0.699248000 -0.160661000 0.384569000
6 1.313822000 -0.908378000 -0.816309000
6 2.809571000 -1.170233000 -0.604853000
6 3.574351000 0.124788000 -0.320609000
6 2.958893000 0.888391000 0.855801000
6 1.462418000 1.144890000 0.644731000
1 -1.120567000 -1.642465000 1.467021000
1 -1.502871000 -1.861301000 -0.241592000
1 -3.059796000 -0.191157000 1.778423000
1 -3.580082000 -1.697392000 1.028796000
1 -4.609709000 0.345331000 -0.070524000
1 -3.667011000 -0.627592000 -1.184506000
1 -2.731786000 1.933415000 0.194415000
1 -3.059513000 1.729585000 -1.523858000
1 -0.626919000 1.648383000 -1.018576000
1 -1.204261000 0.155239000 -1.755893000
1 0.854208000 -0.791276000 1.267124000
1 1.180773000 -0.311571000 -1.723729000
1 0.789668000 -1.852028000 -0.981919000
1 3.229659000 -1.674114000 -1.478427000
1 2.939262000 -1.856954000 0.238624000
1 3.551879000 0.759470000 -1.213021000
1 4.626300000 -0.092656000 -0.121826000
1 3.481558000 1.835286000 1.008247000
1 3.098597000 0.307345000 1.773636000
1 1.338371000 1.825903000 -0.202326000
1 1.026957000 1.640295000 1.514236000
Conformer IIEqC-EqN-twist
E(RB3LYP) = –486.746628212
7 0.728759000 0.031350000 -0.103825000
6 1.437591000 -1.230919000 0.110320000
6 2.839762000 -1.190690000 -0.499077000
6 3.663609000 -0.029982000 0.054818000
6 2.876493000 1.272252000 -0.081493000
6 1.477754000 1.129365000 0.512755000
6 -0.694117000 0.048467000 0.297988000
6 -1.427906000 1.202104000 -0.410910000
6 -2.909383000 1.285045000 -0.032936000
6 -3.632625000 -0.031200000 -0.315433000
6 -2.916754000 -1.193431000 0.371554000
6 -1.430719000 -1.265880000 -0.000867000
1 0.883552000 -2.040089000 -0.356745000
1 1.518063000 -1.471731000 1.187941000
1 2.741970000 -1.086057000 -1.582928000
1 3.337695000 -2.144617000 -0.309945000
1 4.625911000 0.040702000 -0.456483000
1 3.882145000 -0.211710000 1.112374000
1 2.783414000 1.538627000 -1.137564000
1 3.396683000 2.094332000 0.415633000
1 0.933301000 2.060119000 0.372536000
1 1.561995000 0.973093000 1.605324000
1 -0.764348000 0.214433000 1.389597000
1 -1.327404000 1.043164000 -1.488642000
1 -0.949472000 2.156268000 -0.193064000
1 -3.381704000 2.105786000 -0.577343000
1 -3.002153000 1.527430000 1.031088000
1 -3.655402000 -0.206267000 -1.396170000
1 -4.672657000 0.023240000 0.014249000
1 -3.398793000 -2.140999000 0.121025000
1 -3.008264000 -1.079355000 1.456895000
1 -1.329396000 -1.493790000 -1.067175000
1 -0.978675000 -2.092815000 0.545853000
Conformer IIIAxC-EqN
E(RB3LYP) = –486.745199469
7 -0.470328000 -0.000038000 0.220884000
6 -1.287787000 1.198797000 0.427913000
6 -2.495131000 1.245022000 -0.506715000
6 -3.365147000 0.000050000 -0.357178000
6 -2.495191000 -1.244967000 -0.506767000
6 -1.287925000 -1.198830000 0.427933000
6 0.762431000 -0.000097000 1.037664000
6 1.644367000 1.237205000 0.773724000
6 2.196070000 1.267420000 -0.655501000
6 2.998221000 0.000056000 -0.969237000
6 2.196125000 -1.267343000 -0.655623000
6 1.644367000 -1.237294000 0.773620000
1 -0.681712000 2.082579000 0.249626000
1 -1.637105000 1.256701000 1.476933000
1 -2.137670000 1.320939000 -1.537199000
1 -3.069910000 2.150196000 -0.297815000
1 -4.175243000 0.000083000 -1.089305000
1 -3.833956000 0.000021000 0.632430000
1 -2.137684000 -1.320843000 -1.537235000
1 -3.070042000 -2.150118000 -0.297951000
1 -0.681862000 -2.082640000 0.249758000
1 -1.637318000 -1.256599000 1.476924000
1 0.487927000 -0.000145000 2.108141000
1 2.478000000 1.189392000 1.480394000
1 1.120179000 2.163347000 1.004018000
1 2.823309000 2.151655000 -0.791120000
1 1.366589000 1.355236000 -1.360807000
1 3.914544000 0.000069000 -0.368595000
1 3.313594000 0.000088000 -2.015152000
1 2.823376000 -2.151561000 -0.791323000
1 1.366632000 -1.355122000 -1.360923000
1 2.477995000 -1.189580000 1.480303000
1 1.120259000 -2.163537000 1.003710000
MP2/6-311G**
Conformer IEqC-EqN-orth
EUMP2 = –485.16804096307
7 -0.753910000 0.088919000 0.371584000
6 -1.530239000 -1.125865000 0.608364000
6 -2.993267000 -0.767708000 0.866457000
6 -3.566399000 0.008168000 -0.320982000
6 -2.675988000 1.209086000 -0.645667000
6 -1.229787000 0.754397000 -0.840061000
6 0.696021000 -0.150012000 0.400768000
6 1.276402000 -0.891217000 -0.814691000
6 2.767902000 -1.181495000 -0.608661000
6 3.545402000 0.111073000 -0.344495000
6 2.959230000 0.867307000 0.851399000
6 1.466863000 1.150261000 0.645754000
1 -1.106714000 -1.637907000 1.480169000
1 -1.479617000 -1.826178000 -0.249714000
1 -3.041668000 -0.149895000 1.770774000
1 -3.571187000 -1.681737000 1.048438000
1 -4.594160000 0.328774000 -0.116551000
1 -3.601170000 -0.654908000 -1.196493000
1 -2.704698000 1.928147000 0.181330000
1 -3.027400000 1.718096000 -1.551199000
1 -0.590804000 1.617746000 -1.048452000
1 -1.184365000 0.083621000 -1.720900000
1 0.865849000 -0.786130000 1.283613000
1 1.155562000 -0.268059000 -1.710817000
1 0.727831000 -1.824502000 -0.990188000
1 3.177140000 -1.701461000 -1.482869000
1 2.887727000 -1.855975000 0.250664000
1 3.487130000 0.750887000 -1.235993000
1 4.606047000 -0.109057000 -0.175234000
1 3.502313000 1.805687000 1.013318000
1 3.088605000 0.261588000 1.759025000
1 1.350468000 1.820715000 -0.215899000
1 1.033630000 1.654146000 1.516778000
Conformer IIEqC-EqN-twist
EUMP2 = –485.16630565375
7 0.725820000 0.042338000 -0.158430000
6 1.421522000 -1.226900000 0.063926000
6 2.832851000 -1.170671000 -0.522455000
6 3.644834000 -0.032519000 0.092785000
6 2.865750000 1.274890000 -0.039447000
6 1.461639000 1.104973000 0.534005000
6 -0.686338000 0.055276000 0.274436000
6 -1.425620000 1.183287000 -0.460893000
6 -2.895279000 1.285368000 -0.043954000
6 -3.617909000 -0.038256000 -0.294720000
6 -2.893874000 -1.176350000 0.424337000
6 -1.418087000 -1.266239000 0.015698000
1 0.873597000 -2.030133000 -0.431754000
1 1.479334000 -1.472823000 1.145508000
1 2.743138000 -1.014622000 -1.604210000
1 3.327547000 -2.136037000 -0.362085000
1 4.629306000 0.045330000 -0.382106000
1 3.811540000 -0.243522000 1.157895000
1 2.778891000 1.552673000 -1.096499000
1 3.377331000 2.091562000 0.483684000
1 0.908606000 2.042345000 0.438175000
1 1.536301000 0.875916000 1.618107000
1 -0.738664000 0.247814000 1.367447000
1 -1.357588000 0.965441000 -1.534850000
1 -0.925831000 2.142637000 -0.296447000
1 -3.382096000 2.100570000 -0.591756000
1 -2.956034000 1.535478000 1.024290000
1 -3.628590000 -0.241919000 -1.374181000
1 -4.661972000 0.019703000 0.034638000
1 -3.387055000 -2.134495000 0.223147000
1 -2.952169000 -1.008709000 1.508660000
1 -1.342459000 -1.507379000 -1.054144000
1 -0.950817000 -2.083361000 0.573173000
Conformer IIIAxC-EqN
EUMP2 = –485.16845536122
7 0.427217000 -0.000022000 0.195401000
6 1.245255000 -1.193457000 0.428440000
6 2.454264000 -1.240768000 -0.504194000
6 3.325089000 -0.000061000 -0.328737000
6 2.454343000 1.240713000 -0.504342000
6 1.245544000 1.193309000 0.428512000
6 -0.770326000 0.000162000 1.057882000
6 -1.648530000 -1.234753000 0.791641000
6 -2.114101000 -1.269532000 -0.667128000
6 -2.901283000 -0.000002000 -1.012295000
6 -2.113902000 1.269424000 -0.667304000
6 -1.648305000 1.235054000 0.791529000
1 0.637432000 -2.082806000 0.252523000
1 1.591028000 -1.228253000 1.483576000
1 2.091403000 -1.291929000 -1.538081000
1 3.024254000 -2.155713000 -0.303959000
1 4.158230000 -0.000226000 -1.040431000
1 3.756390000 0.000045000 0.681503000
1 2.091450000 1.291842000 -1.538212000
1 3.024366000 2.155641000 -0.304141000
1 0.637661000 2.082706000 0.253187000
1 1.591689000 1.227673000 1.483543000
1 -0.460830000 -0.000013000 2.124103000
1 -2.524524000 -1.157761000 1.449608000
1 -1.142450000 -2.163645000 1.068587000
1 -2.737537000 -2.154922000 -0.841301000
1 -1.239433000 -1.344083000 -1.322955000
1 -3.839207000 0.000110000 -0.438489000
1 -3.175934000 -0.000017000 -2.073799000
1 -2.737182000 2.154876000 -0.841708000
1 -1.239135000 1.343673000 -1.323025000
1 -2.524227000 1.158326000 1.449620000
1 -1.142257000 2.164099000 1.068026000
MP2(Full)/6-311G**
Conformer IEqC-EqN-orth
ENERGY= –485.6895214
7 -0.747753155 0.093829002 0.378121772
6 -1.516003595 -1.115103816 0.608389253
6 -2.972346744 -0.771565767 0.849195770
6 -3.534670779 -0.004334259 -0.333751867
6 -2.660926117 1.199921843 -0.634137256
6 -1.220375725 0.765686701 -0.818564695
6 0.692467601 -0.143719356 0.402616983
6 1.262114150 -0.881337651 -0.804645815
6 2.739453661 -1.178584918 -0.598760060
6 3.517962275 0.101224206 -0.345634298
6 2.940538545 0.860729176 0.836904511
6 1.461191595 1.145810840 0.631019901
1 -1.099673856 -1.621779419 1.475670061
1 -1.454621189 -1.810526928 -0.242324728
1 -3.036688447 -0.158877786 1.745903919
1 -3.540733259 -1.681913146 1.024110182
1 -4.561159985 0.298082085 -0.145772376
1 -3.548363931 -0.657837131 -1.206630348
1 -2.706448193 1.902914765 0.194961221
1 -3.006788336 1.712915598 -1.528371746
1 -0.591862838 1.629079264 -1.011261427
1 -1.164610060 0.111171861 -1.700952777
1 0.864402400 -0.772210181 1.279678626
1 1.147488369 -0.257803510 -1.691371402
1 0.711194836 -1.802111919 -0.982841044
1 3.143510725 -1.705159176 -1.459826294
1 2.854002594 -1.841208018 0.259883176
1 3.461654920 0.731080840 -1.234161610
1 4.569352094 -0.119650000 -0.179521574
1 3.484488377 1.788520102 0.994977669
1 3.066353765 0.262248224 1.739672844
1 1.349041630 1.799287588 -0.233762128
1 1.034628139 1.661878801 1.487015213
Conformer IIEqC-EqN-twist
ENERGY= –485.6879241
7 0.719460132 0.040454700 -0.167448199
6 1.410423527 -1.216710266 0.068161776
6 2.817284154 -1.168913195 -0.496390305
6 3.615463226 -0.034195277 0.113389173
6 2.848392899 1.262201573 -0.054831709
6 1.447868324 1.110992778 0.498967234
6 -0.681274157 0.051079561 0.265802959
6 -1.418825337 1.178891249 -0.444481676
6 -2.873101122 1.274288955 -0.017663701
6 -3.592327625 -0.034564794 -0.282487728
6 -2.869138949 -1.173978805 0.409266417
6 -1.407993507 -1.255441851 -0.007732796
1 0.869670895 -2.017209447 -0.420191143
1 1.457785735 -1.452274845 1.144351724
1 2.744944913 -1.024400603 -1.572660819
1 3.305023486 -2.124994383 -0.322522661
1 4.602325197 0.032606036 -0.336226996
1 3.758659683 -0.227600626 1.176684370
1 2.778963307 1.515065468 -1.110852832
1 3.351927153 2.081951112 0.451908106
1 0.902611269 2.039014450 0.376782413
1 1.509021350 0.909601880 1.581239519
1 -0.730854661 0.228473591 1.352857920
1 -1.359986274 0.975129183 -1.513579293
1 -0.923860455 2.129756961 -0.276574236
1 -3.361080224 2.093165547 -0.540020435
1 -2.924742053 1.502539225 1.047386020
1 -3.609552639 -0.220144745 -1.356639199
1 -4.626057714 0.017863537 0.049773567
1 -3.360241351 -2.121489486 0.202146217
1 -2.920159695 -1.022344352 1.487967545
1 -1.340034579 -1.475282125 -1.074323599
1 -0.940391809 -2.076207609 0.525879674
Conformer IIIAxC-EqN
ENERGY= –485.6899022
7 0.425277656 0.000035972 0.193067367
6 1.233888679 -1.187861962 0.418730443
6 2.436719633 -1.231357030 -0.501260774
6 3.299013039 -0.000148100 -0.317454258
6 2.436891718 1.231187640 -0.501209831
6 1.234058866 1.187809777 0.418781573
6 -0.764491483 0.000124965 1.049156663
6 -1.635811551 -1.224765737 0.786711769
6 -2.096692670 -1.258173734 -0.661144621
6 -2.881538989 -0.000012523 -1.000940759
6 -2.096648835 1.258180671 -0.661359848
6 -1.635760990 1.225016368 0.786500703
1 0.626766934 -2.066389388 0.239389810
1 1.574240431 -1.231369500 1.466703413
1 2.082989559 -1.277286683 -1.529781636
1 3.002024315 -2.139247722 -0.305851734
1 4.134931656 -0.000198123 -1.011495661
1 3.715419833 -0.000198558 0.690039678
1 2.083178719 1.277219934 -1.529731320
1 3.002321624 2.138988155 -0.305744136
1 0.627056267 2.066431182 0.239507365
1 1.574431490 1.231209462 1.466753789
1 -0.457488467 0.000208087 2.106896148
1 -2.505348738 -1.149883620 1.439685276
1 -1.133405058 -2.146658529 1.060709239
1 -2.708424151 -2.139474148 -0.839282790
1 -1.226018490 -1.326014312 -1.310070814
1 -3.808420896 0.000052105 -0.425487293
1 -3.162015576 -0.000100340 -2.051360352
1 -2.708344911 2.139473671 -0.839653814
1 -1.225969427 1.325871396 -1.310293684
1 -2.505291989 1.150302965 1.439501267
1 -1.133306069 2.146937196 1.060315422
Experimental Section
GED/MS
A sample of NCHP was purchased from the Alfa Aesarcompany, 97%. The diffraction patterns of NCHP were obtained in a synchronous gas-phase electron diffraction and mass-spectrometric experiment carried out using the EMR-100/APDM-1 unit [[1], [2]]. The sample of NCHP was evaporated from a molybdenum cell with a cylindrical effusion nozzle of 0.6 × 1.2 mm size (diameter × length) at 302 K. The ratio of the evaporation area to the effusion orifice area was above 400.
Since the compound is relatively volatile even at room temperature, but not volatile enough to apply a gas inlet system, we had to pour the sample directly into the effusion cell filled with pieces of broken Schott filter used as an adsorbent. Since the effusion cell does not contain a shutting valve, it was necessary to slightly cool down the sample in order to avoid a complete loss of the compound when pumping down. For this purpose, we injected cold gas from a liquid nitrogen tank repeatedly, about five times from the very beginning of the diffraction chamber evacuation. The cool trap, surrounding the effusion cell, was filled with liquid nitrogen since diffraction chamber pumping down was initiated. The gaseous nitrogen, being injected between the pumping-down stages, provided an intensive heat-exchange between the cool trap and the effusion cell. This allowed the effusion cell to cool down to ca. –30 oC. The minimal vapor pressure needed for exposure of photographic films was reached at a sample and nozzle temperature of 302 K, as measured by a W–Re (5/20) thermocouple. An advantage of this approach is that it allows the investigation of compounds with intermediate volatility without introducing a shutting valve into an effusion cell.
One set (5 films) and one set (4 films) were recorded from long, L1 = 598 mm, and short, L2 = 338 mm, camera distances, respectively. Accurate wavelengths of electrons have been calibrated using polycrystalline ZnO. The diffraction patterns were recorded using Kodak SO-163 electron image films of size 912 cm2. Two camera distances, long and short, were used resulting in diffraction patterns in the s-range of 1.2 to 16.4 Å–1 and 2.6 to 29.2 Å–1 (s =(4π/λ)sin(/2)), λ is electron wavelength and is scattering angle), respectively.The optical densities of the diffraction patterns were measured by a computer controlled MD-100 (Carl Zeiss, Jena) microdensitometer [[3]] with a step size of 0.1Å. The molecular scattering function, sM(s), was evaluated as sM(s)=(I(s)/G(s)–1)s, where I(s)is the total electron scattering intensity, G(s) the experimental background. Least-squares analysis of the scattering intensities was performed using a modified in Ivanovo version of program KCED-35 [[4]] by minimizing an agreement functional Rf expressed as:
where: ωi – weight function; k– scale coefficient, k=siMexp.(si)/siMtheor.(si), siMexp.(si), siMtheor.(si) – experimental and theoretical molecular scattering intensities, respectively.
Table S1 Conditions of the synchronous GED/MS experiments.
Long / ShortNozzle-to-plate distance, mm / 598 / 338
Number of recorded films / 5 / 4
Primary electron beam current, A / 1.03 / 1.42
Accelerating voltagea, kV / 83 / 85
Temperature of effusion cell, K / 301(5) / 303(5)
Wavelength of electronsb, Å / 0.04091(3) / 0.04046(3)
Exposure time, s / 60 / 110
Residual gas pressure, Torr, in
–diffraction chamber / 3.3·10-6 / 2.2·10–6
–mass spectrometric block / 5.5·10-7 / 5.7·10–7
Ionization voltage, V / 50
aApproximate value
bAccurate wavelengths of electrons were calibrated using diffractions pattern of polycrystalline ZnO
Mass-spectrometric
Fig. S1EI (50 eV) mass spectra of NCHP
Fig. S2 Mass spectra of NCHP at different ionizing electrons energies, Ui recorded in high-speed low resolution mode.
QST3 calculations
Fig. S3 The energy pathway for the equatorial-to-axial interconversion of cyclohexane ring of NCHP calculated by the STQN method with keywords QST3 and PATH at B3LYP/cc-pVTZ level. Chair(II), chair(III) and twist structures were set as input minima.
Table S2 Relative total electron and free Gibbs energies of the all possible conformers of molecule NCHP
Methods/basis set / ∆E, kcal/moleI / II / III / IV / V / VI / VII / VIII
B3LYP/cc-pVTZ / 0 / 1.25 / 2.14 / 5.07 / 4.41 / 4.41 / 5.43 / 9.83
MP2/6-311G** / 0 / 1.09 / –0.26 / 4.70 / 3.11 / 4.58 / 1.99 / 9.21
∆Go(298K), kcal/mole
I / II / III / IV / V / VI / VII / VIII
B3LYP/cc-pVTZ / 0 / 1.09 / 2.23 / 5.03 / 4.16 / 3.85 / 5.70 / 9.55
MP2/6-311G** / 0 / 1.19 / –0.02 / 4.91 / 2.59 / 4.59 / 2.72 / 9.76
Table S3 Lowest vibrational frequencies* of the conformers I,II and III (cm–1)
Methods/basis set / ν, cm–1I / II / III
B3LYP/6-311G** / 69.1 / 45.7 / 31.5
B3LYP/6-311+G** / 70.5 / 42.4 / 30.4
B3LYP/cc-pVTZ / 69.7 / 43.3 / 31.4
MP2(FC)/6-311G** / 65.6 / 56.4 / 34.4
MP2(FC)/6-311+G** / 64.7 / 49.9 / 34.7
MP2(Full)/6-311G** / 65.8 / 56.7 / 34.9
MP2(Full)/cc-pVTZ / 64.3 / 54.1 / 28.5
* – Twist frequency of both cycles around bond N-C
Table S4a Theoretical and experimental geometric parameters[a] of conformer I
Parameter / EqC_EqN-orth (Conformer I) / GED[b]B3LYP / MP2 / MP2(Full)
6-311G** / 6-311+G** / cc-pVTZ / 6-311G** / 6-311+G** / cc-pVTZ
Bond distances
N–C1 / 1.462 / 1.463 / 1.459 / 1.461 / 1.462 / 1.451 / 1.460(3)
C1-C2 / 1.532 / 1.532 / 1.528 / 1.528 / 1.528 / 1.516 / 1.535(3)
N-C6 / 1.473 / 1.473 / 1.470 / 1.470 / 1.471 / 1.460 / 1.469(3)
C6-C7 / 1.546 / 1.546 / 1.542 / 1.537 / 1.538 / 1.525 / 1.544(3)
C6-C11 / 1.538 / 1.538 / 1.534 / 1.531 / 1.531 / 1.519 / 1.538(3)
C7-C8 / 1.537 / 1.537 / 1.533 / 1.533 / 1.534 / 1.521 / 1.540(3)
C8-C9 / 1.534 / 1.534 / 1.531 / 1.531 / 1.531 / 1.519 / 1.538(3)
C-Heq(av) / 1.094 / 1.095 / 1.092 / 1.096 / 1.096 / 1.087 / 1.106(3)
C-Hax(av) / 1.099 / 1.099 / 1.096 / 1.100 / 1.101 / 1.092 / 1.110(3)
Bond angles
N-C1-C2 / 110.8 / 111.0 / 111.0 / 110.0 / 110.2 / 110.2 / 108.5(10)
C1-C2-C3 / 110.9 / 110.9 / 111.0 / 110.3 / 110.4 / 110.3 / 110.5(3)
C1-N-C6 / 114.0 / 113.9 / 114.0 / 112.7 / 112.7 / 112.6 / 112.9(18)
N-C6-C7 / 115.8 / 115.3 / 115.8 / 115.8 / 115.7 / 115.7 / 112.7(31)
C6-C7-C8 / 111.3 / 111.3 / 111.4 / 110.6 / 110.5 / 110.5 / 110.8(3)
C7-C6-C11 / 110.3 / 110.3 / 110.3 / 110.2 / 110.1 / 109.9 / 110.4(3)
N-C1-H1 / 108.3 / 108.3 / 108.3 / 108.2 / 108.2 / 108.2 / 107.3(30)
C2-C1-H1 / 109.8 / 109.9 / 109.9 / 110.2 / 110.3 / 110.3 / 110.4(4)
∑CNC / 341.4 / 341.2 / 341.6 / 336.9 / 336.8 / 336.9 / 338.4(54)
Dihedral angles
N-C1-C2-C3 / 56.1 / 56.0 / 55.9 / 58.1 / 57.9 / 57.9 / 59.1(19)
C1-N-C6-C7 / 75.2 / 74.6 / 74.8 / 73.2 / 73.3 / 72.8 / 70.8(58)
N-C6-C7-C8 / -176.0 / -175.8 / -175.8 / -175.2 / -175.0 / -174.8 / -170.8(43)
C6-C7-C8-C9 / -55.5 / -55.6 / -55.5 / -56.9 / -57.1 / -57.3 / -57.1(17)
C7-C8-C9-C10 / 54.4 / 54.4 / 54.3 / 56.0 / 55.9 / 56.0 / 56.2(17)
Flap 1[c] / 54.6 / 54.1 / 54.6 / 57.3 / 56.8 / 56.5 / 59(2)
Flap 2[c] / 47.6 / 47.6 / 47.5 / 48.7 / 48.7 / 49.0 / 49(2)
Flap 3[c] / 50.4 / 50.5 / 50.5 / 52.1 / 52.4 / 52.7 / 51(2)
Flap 4[c] / 49.1 / 49.1 / 49.0 / 50.7 / 50.7 / 50.8 / 51(2)
Table S4b Theoretical and experimental geometric parameters[a]of conformer II
Parameter / EqC_EqN-twist (Conformer II) / GED[b]B3LYP / MP2 / MP2(Full)
6-311G** / 6-311+G** / cc-pVTZ / 6-311G** / 6-311+G** / cc-pVTZ
Bond distances
N–C1 / 1.467 / 1.467 / 1.463 / 1.464 / 1.465 / 1.454 / 1.463(3)
C1-C2 / 1.533 / 1.533 / 1.529 / 1.529 / 1.529 / 1.517 / 1.536(3)
N-C6 / 1.481 / 1.482 / 1.479 / 1.477 / 1.478 / 1.466 / 1.476(3)
C6-C7 / 1.544 / 1.544 / 1.540 / 1.536 / 1.536 / 1.523 / 1.543(3)
C6-C11 / 1.540 / 1.540 / 1.536 / 1.533 / 1.533 / 1.520 / 1.540(3)
C7-C8 / 1.535 / 1.535 / 1.531 / 1.531 / 1.531 / 1.519 / 1.538(3)
C8-C9 / 1.532 / 1.532 / 1.528 / 1.529 / 1.529 / 1.517 / 1.536(3)
C-Heq(av) / 1.093 / 1.093 / 1.091 / 1.095 / 1.095 / 1.086 / 1.105(3)
C-Hax(av) / 1.100 / 1.101 / 1.098 / 1.102 / 1.102 / 1.093 / 1.112(3)
Bond angles
N-C1-C2 / 111.0 / 111.3 / 111.3 / 110.4 / 110.7 / 110.7 / 108.9(10)
C1-C2-C3 / 111.6 / 111.7 / 111.7 / 111.3 / 111.4 / 111.3 / 111.5(3)
C1-N-C6 / 116.0 / 115.6 / 115.9 / 114.7 / 114.3 / 114.4 / 114.9(18)
N-C6-C7 / 109.7 / 110.1 / 110.0 / 109.0 / 109.4 / 109.3 / 105.9(31)
C6-C7-C8 / 112.8 / 112.8 / 112.8 / 112.4 / 112.3 / 112.3 / 112.6(3)
C7-C6-C11 / 108.9 / 108.8 / 108.8 / 108.8 / 108.8 / 108.7 / 109.0(3)
N-C1-H1 / 109.4 / 109.4 / 109.4 / 109.3 / 109.3 / 109.2 / 108.4(30)
C2-C1-H1 / 108.4 / 108.4 / 108.4 / 108.4 / 108.5 / 108.6 / 108.6(4)
∑CNC / 337.2 / 336.8 / 337.2 / 332.8 / 332.8 / 333.0 / 333.9(54)
Dihedral angles
N-C1-C2-C3 / 56.9 / 56.7 / 56.7 / 58.3 / 58.1 / 58.2 / 59.4(19)
C1-N-C6-C7 / -158.7 / -160.7 / -160.1 / -158.9 / -161.4 / -160.3 / -150(15)
N-C6-C7-C8 / -179.6 / -179.6 / -179.6 / -178.7 / -178.9 / -177.8 / -174.3(43)
C6-C7-C8-C9 / -56.3 / -56.4 / -56.3 / -57.6 / -57.7 / -56.9 / -57.9(17)
C7-C8-C9-C10 / 54.1 / 54.2 / 54.1 / 55.9 / 55.6 / 55.7 / 54.6(17)
Flap 1[c] / 54.2 / 53.5 / 53.6 / 55.8 / 55.0 / 54.8 / 58(2)
Flap 2[c] / 47.1 / 47.1 / 47.0 / 48.3 / 48.3 / 48.7 / 48(2)
Flap 3[c] / 49.5 / 49.5 / 49.4 / 50.8 / 50.8 / 51.1 / 50(2)
Flap 4[c] / 49.0 / 49.0 / 48.9 / 50.6 / 50.5 / 50.7 / 51(2)
Table S4c Theoretical and experimental geometric parameters[a] of conformer III
B3LYP / MP2 / MP2(Full)
6-311G** / 6-311+G** / cc-pVTZ / 6-311G** / 6-311+G** / cc-pVTZ
Bond distances
N–C1 / 1.469 / 1.469 / 1.466 / 1.466 / 1.465 / 1.455 / 1.465(3)
C1-C2 / 1.531 / 1.531 / 1.528 / 1.528 / 1.527 / 1.515 / 1.535(3)
N-C6 / 1.482 / 1.482 / 1.479 / 1.476 / 1.476 / 1.466 / 1.475(3)
C6-C7 / 1.546 / 1.546 / 1.542 / 1.539 / 1.538 / 1.526 / 1.546(3)
C6-C11 / 1.546 / 1.546 / 1.542 / 1.538 / 1.538 / 1.526 / 1.546(3)
C7-C8 / 1.536 / 1.536 / 1.532 / 1.532 / 1.532 / 1.520 / 1.539(3)
C8-C9 / 1.536 / 1.536 / 1.532 / 1.533 / 1.533 / 1.521 / 1.540(3)
C-Heq(av) / 1.094 / 1.094 / 1.092 / 1.096 / 1.096 / 1.087 / 1.107(3)
C-Hax(av) / 1.099 / 1.099 / 1.096 / 1.100 / 1.101 / 1.092 / 1.110(3)
Bond angles
N-C1-C2 / 112.1 / 112.3 / 112.3 / 111.7 / 111.8 / 111.8 / 110.2(10)
C1-C2-C3 / 111.4 / 111.4 / 111.5 / 110.9 / 110.9 / 110.8 / 111.1(3)
C1-N-C6 / 112.7 / 112.7 / 112.8 / 111.1 / 111.3 / 111.1 / 111.3(18)
N-C6-C7 / 112.3 / 112.4 / 112.5 / 111.2 / 111.4 / 111.3 / 108.1(31)
C6-C7-C8 / 112.2 / 112.4 / 112.4 / 110.9 / 111.0 / 110.8 / 111.0(3)
C7-C6-C11 / 106.7 / 106.7 / 106.7 / 106.8 / 106.8 / 106.8 / 107.0(3)
N-C1-H1 / 109.3 / 109.3 / 109.3 / 109.1 / 109.1 / 109.0 / 108.2(30)
C2-C1-H1 / 108.4 / 108.4 / 108.4 / 108.5 / 108.6 / 108.7 / 108.7(4)
∑CNC / 335.1 / 335.2 / 335.3 / 331.2 / 331.8 / 331.7 / 332.5(54)
Torsion angles
N-C1-C2-C3 / 56.8 / 56.6 / 56.6 / 58.2 / 58.1 / 60.0 / 59.3()
C1-N-C6-C7 / -57.5 / -57.3 / -57.3 / -59.8 / -59.4 / -59.4 / -59.8()
N-C6-C7-C8 / -64.2 / -64.8 / -64.0 / -59.7 / -60.3 / -59.7 / -59.7()
C6-C7-C8-C9 / -57.3 / -57.1 / -57.1 / -58.4 / -58.4 / -58.7 / -58.7()
C7-C8-C9-C10 / 52.4 / 52.3 / 52.3 / 53.3 / 53.4 / 53.6 / 53.5()
Flap 1[c] / 52.3 / 52.0 / 52.0 / 53.5 / 53.3 / 53.0 / 55 (2)
Flap 2[c] / 47.6 / 47.6 / 47.5 / 49.0 / 49.0 / 49.4 / 49(2)
Flap 3[c] / 52.6 / 52.4 / 52.2 / 55.4 / 55.2 / 55.6 / 55(2)
Flap 4[c] / 47.6 / 47.6 / 47.5 / 48.6 / 48.7 / 49.0 / 49(2)
[a] Distances in Å, angles in degrees; re and e values (calculations) and rh1 (rh1=ra+Δr) and h1 (GED) are given. The vibrational corrections ∆r were calculated by the SHRINK program [[5],[6]] using the so called second approximation, in which a harmonic approach with nonlinear relation between Cartesian and internal coordinates was applied on the base of the force field estimated in the quantum chemical calculations at MP2/6-311G** level.
[b] Values in parentheses for the GED data are full errors estimated as (rh1)=[scale2+(2.5LS)2]½, where scale =0.002r and LS is a standard deviation in least-squares refinement for internuclear distances and as 3LS for angles. The place-value is such that the last digit of the uncertainty lines up with the last digit of the nominal value.
[c]Flap 1 and Flap 2 are angles between N-C5-C1 and C-1-C2…C4-C5 planes and between C3-C4-C2 and C1-C2…C4-C5 planes, respectively; Flap 3 and Flap 4 are angles between C6-C11-C7 and C-7-C8…C10-C11 planes and between C9-C10-C8 and C7-C8…C10-C11 planes, respectively; dependent parameters, uncertainties are approximate.
Table S5a Theoretical geometric parameters[a] of conformers IV, V and VI
IV / V / VIConformers / IV / V / VI
Methods / B3LYP / MP2 / B3LYP / MP2 / B3LYP / MP2
Basis set / cc-pVTZ / 6-311G** / cc-pVTZ / 6-311G** / cc-pVTZ / 6-311G**
Bond distances
N–C1 / 1.460 / 1.462 / 1.465 / 1.471 / 1.455 / 1.458
C1-C2 / 1.529 / 1.529 / 1.536 / 1.534 / 1.537 / 1.536
N-C6 / 1.475 / 1.475 / 1.478 / 1.476 / 1.463 / 1.464
C6-C7 / 1.553 / 1.547 / 1.535 / 1.535 / 1.539 / 1.536
C6-C11 / 1.547 / 1.542 / 1.541 / 1.535 / 1.545 / 1.541
C7-C8 / 1.534 / 1.535 / 1.533 / 1.532 / 1.532 / 1.532
C8-C9 / 1.530 / 1.530 / 1.529 / 1.527 / 1.530 / 1.530
C-Heq(av) / 1.092 / 1.096 / 1.091 / 1.095 / 1.092 / 1.096
C-Hax(av) / 1.096 / 1.100 / 1.096 / 1.099 / 1.095 / 1.099
Bond angles
N-C1-C2 / 111.0 / 110.1 / 114.5 / 113.7 / 114.9 / 115.2
C1-C2-C3 / 111.1 / 110.4 / 110.3 / 108.0 / 110.2 / 109.4
C1-N-C6 / 118.1 / 115.9 / 118.0 / 114.0 / 118.6 / 117.0
N-C6-C7 / 116.8 / 116.4 / 112.7 / 110.2 / 111.1 / 110.0
C6-C7-C8 / 115.4 / 115.1 / 112.2 / 112.5 / 112.2 / 111.8
C7-C6-C11 / 111.2 / 111.7 / 109.0 / 109.5 / 109.9 / 109.6
N-C1-H1 / 109.1 / 109.1 / 109.9 / 109.9 / 108.7 / 108.3
C2-C1-H1 / 109.3 / 109.7 / 111.0 / 111.3 / 110.7 / 111.0
∑CNC / 342.5 / 337.2 / 341.3 / 335.0 / 351.2 / 346.5
Torsion angles
N-C1-C2-C3 / 56.5 / 58.7 / 55.9 / 57.4 / 53.1 / 54.8
C1-N-C6-C7 / 61.1 / 53.5 / 36.9 / 56.2 / 145.2 / 145.8
N-C6-C7-C8 / -89.0 / -88.2 / 176.7 / 174.6 / -174.5 / -173.2
C6-C7-C8-C9 / -52.4 / -52.6 / -55.6 / -56.4 / -55.2 / -56.3
C7-C8-C9-C10 / 57.4 / 59.1 / 54.1 / 56.7 / 54.4 / 55.6
Flap 1[b] / 53.8 / 57.0 / 49.6 / 52.5 / 44.9 / 45.0
Flap 2[b] / 47.9 / 48.9 / 47.4 / 47.3 / 49.0 / 50.9
Flap 3[b] / 38.2 / 38.0 / 49.1 / 48.0 / 49.0 / 49.4
Flap 4[b] / 51.7 / 53.2 / 48.6 / 51.0 / 49.0 / 49.3
Table S5b Theoretical geometric parameters[a] ofconformers VII and VIII
VII / VIIIConformers / VII / VIII
Methods / B3LYP / MP2 / B3LYP / MP2
Basis set / cc-pVTZ / 6-311G** / cc-pVTZ / 6-311G**
Bond distances
N–C1 / 1.468 / 1.468 / 1.458 / 1.462
C1-C2 / 1.536 / 1.535 / 1.539 / 1.538
N-C6 / 1.478 / 1.473 / 1.469 / 1.473
C6-C7 / 1.542 / 1.537 / 1.549 / 1.542
C6-C11 / 1.542 / 1.538 / 1.554 / 1.548
C7-C8 / 1.532 / 1.531 / 1.533 / 1.531
C8-C9 / 1.532 / 1.533 / 1.531 / 1.532
C-Heq(av) / 1.092 / 1.096 / 1.091 / 1.096
C-Hax(av) / 1.094 / 1.098 / 1.095 / 1.098
Bond angles
N-C1-C2 / 114.2 / 113.7 / 114.6 / 115.3
C1-C2-C3 / 110.6 / 109.9 / 110.9 / 110.4
C1-N-C6 / 115.6 / 113.9 / 122.3 / 120.7
N-C6-C7 / 111.8 / 110.4 / 113.0 / 111.1
C6-C7-C8 / 112.6 / 111.2 / 115.7 / 113.9
C7-C6-C11 / 107.2 / 107.4 / 109.6 / 109.2
N-C1-H1 / 110.1 / 109.8 / 109.8 / 109.7
C2-C1-H1 / 110.6 / 111.1 / 110.5 / 110.9
∑CNC / 339.5 / 335.6 / 351.5 / 345.4
Torsion angles
N-C1-C2-C3 / 55.8 / 57.0 / 52.5 / 52.6
C1-N-C6-C7 / 176.1 / 177.3 / 78.6 / 90.9
N-C6-C7-C8 / -65.0 / -60.0 / -87.3 / -82.1
C6-C7-C8-C9 / -56.7 / -57.9 / -52.4 / -56.5
C7-C8-C9-C10 / 52.8 / 53.8 / 54.8 / 56.5
Flap 1[b] / 50.7 / 52.1 / 45.9 / 46.5
Flap 2[b] / 46.5 / 47.5 / 47.6 / 47.6
Flap 3[b] / 51.3 / 54.2 / 41.4 / 46.0
Flap 4[b] / 47.9 / 49.1 / 49.5 / 51.3
[a] Distances in Å, angles in degrees;[b]Flap 1 and Flap 2 are angles between N-C5-C1 and C-1-C2…C4-C5 planes and between C3-C4-C2 and C1-C2…C4-C5 planes, respectively; Flap 3 and Flap 4 are angles between C6-C11-C7 and C-7-C8…C10-C11 planes and between C9-C10-C8 and C7-C8…C10-C11 planes, respectively; dependent parameters, uncertainties are approximate.
Table S6Theoretical (MP2/6-311G**) and experimental[a] (GED) root-mean square vibration amplitudes l and theoretical vibration corrections ∆r, Å without those for nonbonded distances involving hydrogen atoms
Conformer IEqC-EqN-orth
Atompair / Atom
numbers / Multiply / Theoretical / Experimental[b] / Group
№[c] / ∆r[a]
r / l / r / l
C H / 6-21 / 1 / 1.094 / 0.076 / 1.104(2) / 0.078(1) / 1 / 0.00125
C H / 12-33,4-17 / 2 / 1.096 / 0.076 / 1.106(2) / 0.078(1) / 1 / 0.00136
C H / 2-13,11-30,3-15,
5-19,9-26 10-29 / 6 / 1.096 / 0.076 / 1.107(2) / 0.078(1) / 1 / 0.00131
C H / 3-16,5-20,8-25 / 3 / 1.097 / 0.076 / 1.107(2) / 0.078(1) / 1 / 0.00137
C H / 12-32,8-24 / 2 / 1.098 / 0.077 / 1.108(2) / 0.079(1) / 1 / 0.00128
C H / 4-18,11-31,
10-28,9-27 / 4 / 1.099 / 0.077 / 1.109(2) / 0.079(1) / 1 / 0.00125
C H / 7-23 / 1 / 1.101 / 0.077 / 1.112(2) / 0.079(1) / 1 / 9.30E-04
C H / 6-2 / 1 / 1.108 / 0.078 / 1.118(2) / 0.080(1) / 1 / 0.00108
C H / 2-14 / 1 / 1.109 / 0.078 / 1.119(2) / 0.080(1) / 1 / 0.00109
N C / 1-2 / 1 / 1.461 / 0.049 / 1.460(3) / 0.053(2) / 2 / 8.70E-04
N C / 1-6 / 1 / 1.462 / 0.049 / 1.461(3) / 0.053(2) / 2 / 8.00E-04
N C / 1-7 / 1 / 1.470 / 0.049 / 1.469(3) / 0.054(2) / 2 / 4.50E-04
C C / 2-3,5-6 / 2 / 1.528 / 0.050 / 1.535(3) / 0.055(2) / 2 / 5.00E-04
C C / 3-4,4-5 / 2 / 1.530 / 0.050 / 1.537(3) / 0.055(2) / 2 / 3.60E-04
C C / 7-12,9-10,10-11 / 3 / 1.531 / 0.051 / 1.538(3) / 0.055(2) / 2 / 4.40E-04
C C / 11-12 / 1 / 1.533 / 0.051 / 1.540(3) / 0.055(2) / 2 / 5.90E-04
C C / 8-9 / 1 / 1.533 / 0.051 / 1.540(3) / 0.055(2) / 2 / 5.60E-04
C C / 7-8 / 1 / 1.537 / 0.052 / 1.544(3) / 0.056(2) / 2 / 8.30E-04
C C / 2-6 / 1 / 2.395 / 0.066 / 2.405(5) / 0.066(4) / 3 / 0.00292
C C / 2-7 / 1 / 2.440 / 0.066 / 2.441(5) / 0.066(4) / 3 / 0.00192
N C / 1-5 / 1 / 2.446 / 0.064 / 2.452(5) / 0.064(4) / 3 / 0.00359
N C / 1-3 / 1 / 2.448 / 0.064 / 2.431(5) / 0.065(4) / 3 / 0.00367
C C / 6-7 / 1 / 2.463 / 0.066 / 2.464(5) / 0.067(4) / 3 / 0.00211
N C / 1-12 / 1 / 2.477 / 0.066 / 2.566(5) / 0.067(4) / 3 / 0.00295
C C / 4-6 / 1 / 2.510 / 0.068 / 2.524(5) / 0.068(4) / 3 / 0.00340
C C / 3-5,2-4 / 2 / 2.509 / 0.068 / 2.523(5) / 0.068(4) / 3 / 0.00373
C C / 8-12 / 1 / 2.517 / 0.069 / 2.532(5) / 0.069(4) / 3 / 0.00384
C C / 7-11 / 1 / 2.522 / 0.068 / 2.554(5) / 0.069(4) / 3 / 0.00463
C C / 9-11 / 1 / 2.523 / 0.068 / 2.537(5) / 0.069(4) / 3 / 0.00344
C C / 8-10,7-9 / 2 / 2.525 / 0.069 / 2.539(5) / 0.069(4) / 3 / 0.00428
C C / 10-12 / 1 / 2.526 / 0.069 / 2.540(5) / 0.069(4) / 3 / 0.00394
N C / 1-8 / 1 / 2.548 / 0.067 / 2.508(5) / 0.068(4) / 3 / 0.00248
C C / 2-5,3-6 / 2 / 2.887 / 0.071 / 2.910(6) / 0.080(4) / 4 / 0.00500
N C / 1-4 / 1 / 2.898 / 0.071 / 2.893(6) / 0.080(4) / 4 / 0.00545
C C / 8-11,9-12 / 2 / 2.950 / 0.073 / 2.973(6) / 0.083(4) / 4 / 0.00552
C C / 7-10 / 1 / 2.957 / 0.072 / 2.980(6) / 0.082(4) / 4 / 0.00646
C C / 6-8 / 1 / 3.001 / 0.134 / 2.981(6) / 0.143(4) / 4 / 0.00327
C C / 6-12 / 1 / 3.102 / 0.117 / 3.200(6) / 0.126(4) / 4 / 0.00482
C C / 2-8 / 1 / 3.156 / 0.134 / 3.083(6) / 0.143(4) / 4 / 0.00323
C C / 2-12 / 1 / 3.764 / 0.077 / 3.825(8) / 0.078(7) / 5 / 0.01261
C C / 3-7 / 1 / 3.769 / 0.070 / 3.755(7) / 0.072(7) / 5 / 0.00813
C C / 5-7 / 1 / 3.783 / 0.071 / 3.788(8) / 0.072(7) / 5 / 0.00808
N C / 1-11 / 1 / 3.825 / 0.070 / 3.902(8) / 0.071(7) / 5 / 0.00904
N C / 1-9 / 1 / 3.870 / 0.070 / 3.851(8) / 0.072(7) / 5 / 0.00858
C C / 4-7 / 1 / 4.326 / 0.074 / 4.331(9) / 0.091(8) / 6 / 0.01070
C C / 5-12 / 1 / 4.340 / 0.123 / 4.456(9) / 0.141(8) / 6 / 0.00995
N C / 1-10 / 1 / 4.359 / 0.076 / 4.394(9) / 0.093(8) / 6 / 0.01201
C C / 6-9 / 1 / 4.449 / 0.120 / 4.455(9) / 0.137(8) / 6 / 0.00963
C C / 2-9 / 1 / 4.468 / 0.133 / 4.385(9) / 0.150(8) / 6 / 0.00780
C C / 5-8 / 1 / 4.480 / 0.121 / 4.460(9) / 0.138(8) / 6 / 0.01033
C C / 6-11 / 1 / 4.518 / 0.102 / 4.606(9) / 0.119(8) / 6 / 0.01103
C C / 3-8 / 1 / 4.591 / 0.116 / 4.530(9) / 0.133(8) / 6 / 0.01024
C C / 6-10 / 1 / 4.844 / 0.126 / 4.903(10) / 0.143(8) / 6 / 0.01100
C C / 3-12 / 1 / 4.860 / 0.104 / 4.924(10) / 0.121(8) / 6 / 0.01753
C C / 2-11 / 1 / 4.919 / 0.093 / 4.954(10) / 0.110(8) / 6 / 0.01560
C C / 4-8 / 1 / 4.951 / 0.124 / 4.919(10) / 0.142(8) / 6 / 0.01011
C C / 4-12 / 1 / 5.251 / 0.102 / 5.350(11) / 0.120(8) / 6 / 0.01754
C C / 2-10 / 1 / 5.311 / 0.101 / 5.288(11) / 0.118(8) / 6 / 0.01582
C C / 5-11 / 1 / 5.841 / 0.116 / 5.951(12) / 0.136(22) / 7 / 0.02001
C C / 5-9 / 1 / 5.947 / 0.110 / 5.951(12) / 0.130(22) / 7 / 0.01967
C C / 3-9 / 1 / 5.962 / 0.120 / 5.892(12) / 0.140(22) / 7 / 0.01833
C C / 3-11 / 1 / 6.173 / 0.103 / 6.218(12) / 0.123(22) / 7 / 0.02367
C C / 5-10 / 1 / 6.326 / 0.131 / 6.399(13) / 0.151(22) / 7 / 0.02252
C C / 4-9 / 1 / 6.452 / 0.120 / 6.424(13) / 0.140(22) / 7 / 0.02039
C C / 4-11 / 1 / 6.686 / 0.093 / 6.769(13) / 0.113(22) / 7 / 0.02603
C C / 3-10 / 1 / 6.708 / 0.090 / 6.702(13) / 0.110(22) / 7 / 0.02594
C C / 4-10 / 1 / 7.113 / 0.106 / 7.152(14) / 0.126(22) / 7 / 0.02706
Conformer IIEqC-EqN-twist
Atompair / Atom
numbers / Multiply / Theoretical / Experimental[b] / Group
№[c] / ∆r[a]
r / l / r / l
C H / 2-13 / 1 / 1.091 / 0.076 / 1.102(2) / 0.078(1) / 1 / 0.00118
C H / 6-21 / 1 / 1.093 / 0.076 / 1.103(2) / 0.078(1) / 1 / 0.00123
C H / 12-33,8-25 / 2 / 1.094 / 0.076 / 1.104(2) / 0.078(1) / 1 / 0.00131
C H / 4-17 / 1 / 1.096 / 0.076 / 1.106(2) / 0.078(1) / 1 / 0.00136
C H / 9-26,11-30,
10-29,5-19 / 4 / 1.096 / 0.076 / 1.106(2) / 0.078(1) / 1 / 0.00133
C H / 3-16,5-20,3-15 / 3 / 1.097 / 0.076 / 1.107(2) / 0.078(1) / 1 / 0.00134
C H / 8-24 / 1 / 1.098 / 0.077 / 1.108(2) / 0.079(1) / 1 / 0.00128
C H / 4-18,10-28 / 2 / 1.098 / 0.077 / 1.109(2) / 0.079(1) / 1 / 0.00126
C H / 9-27,11-31 / 2 / 1.099 / 0.077 / 1.109(2) / 0.079(1) / 1 / 0.00126
C H / 12-32 / 1 / 1.099 / 0.077 / 1.110(2) / 0.079(1) / 1 / 0.00128
C H / 6-22,2-14 / 2 / 1.111 / 0.079 / 1.121(2) / 0.081(1) / 1 / 0.00109
C H / 7-23 / 1 / 1.111 / 0.079 / 1.121(2) / 0.081(1) / 1 / 9.30E-04
N C / 1-2 / 1 / 1.464 / 0.049 / 1.463(3) / 0.054(2) / 2 / 8.70E-04
N C / 1-6 / 1 / 1.466 / 0.049 / 1.465(3) / 0.054(2) / 2 / 8.40E-04
N C / 1-7 / 1 / 1.477 / 0.050 / 1.476(3) / 0.054(2) / 2 / 5.30E-04
C C / 5-6 / 1 / 1.526 / 0.050 / 1.533(3) / 0.055(2) / 2 / 5.30E-04
C C / 3-4,4-5 / 2 / 1.527 / 0.050 / 1.534(3) / 0.055(2) / 2 / 3.50E-04
C C / 10-11,9-10 / 2 / 1.529 / 0.050 / 1.536(3) / 0.055(2) / 2 / 2.80E-04
C C / 2-3 / 1 / 1.529 / 0.050 / 1.536(3) / 0.055(2) / 2 / 4.60E-04
C C / 8-9 / 1 / 1.531 / 0.051 / 1.538(3) / 0.055(2) / 2 / 5.50E-04
C C / 7-12 / 1 / 1.533 / 0.051 / 1.540(3) / 0.056(2) / 2 / 7.30E-04
C C / 11-12 / 1 / 1.534 / 0.051 / 1.541(3) / 0.055(2) / 2 / 5.80E-04
C C / 7-8 / 1 / 1.536 / 0.051 / 1.543(3) / 0.056(2) / 2 / 7.40E-04
H H / 24-25 / 1 / 1.761 / 0.123 / 1.765(4) / 0.128(2) / 2 / 0.00827
H H / 30-31 / 1 / 1.763 / 0.123 / 1.767(4) / 0.128(2) / 2 / 0.00812
H H / 26-27 / 1 / 1.764 / 0.123 / 1.769(4) / 0.128(2) / 2 / 0.00814
H H / 28-29 / 1 / 1.767 / 0.123 / 1.772(4) / 0.128(2) / 2 / 0.00810
H H / 17-18 / 1 / 1.768 / 0.123 / 1.772(4) / 0.128(2) / 2 / 0.00805
H H / 32-33 / 1 / 1.771 / 0.123 / 1.760(4) / 0.128(2) / 2 / 0.00792
H H / 15-16 / 1 / 1.774 / 0.123 / 1.778(4) / 0.128(2) / 2 / 0.00820
H H / 19-20,21-22 / 2 / 1.773 / 0.123 / 1.778(4) / 0.128(2) / 2 / 0.00797
H H / 13-14 / 1 / 1.779 / 0.123 / 1.828(4) / 0.128(2) / 2 / 0.00749
H H / 21-25 / 1 / 1.979 / 0.228 / 2.072(4) / 0.228(4) / 3 / -0.04446
H H / 13-33 / 1 / 2.084 / 0.235 / 2.389(5) / 0.235(4) / 3 / -0.02880
N H / 1-21 / 1 / 2.096 / 0.103 / 2.091(4) / 0.103(4) / 3 / 0.00565
N H / 1-13 / 1 / 2.096 / 0.102 / 2.091(4) / 0.103(4) / 3 / 0.00564
N H / 1-22 / 1 / 2.123 / 0.102 / 2.119(4) / 0.102(4) / 3 / 0.00599
N H / 1-23 / 1 / 2.125 / 0.102 / 2.081(4) / 0.102(4) / 3 / 0.00445
C H / 7-24 / 1 / 2.134 / 0.108 / 2.150(4) / 0.108(4) / 3 / 0.00715
N H / 1-14 / 1 / 2.136 / 0.102 / 2.132(4) / 0.102(4) / 3 / 0.00595
C H / 2-15 / 1 / 2.139 / 0.107 / 2.155(4) / 0.108(4) / 3 / 0.00690
C H / 12-23 / 1 / 2.141 / 0.107 / 2.157(4) / 0.107(4) / 3 / 0.00590
C H / 3-13 / 1 / 2.141 / 0.105 / 2.157(4) / 0.105(4) / 3 / 0.00616
C H / 6-19 / 1 / 2.143 / 0.107 / 2.160(4) / 0.107(4) / 3 / 0.00692
C H / 11-33 / 1 / 2.149 / 0.105 / 2.166(4) / 0.106(4) / 3 / 0.00618
C H / 5-18 / 1 / 2.153 / 0.107 / 2.169(4) / 0.107(4) / 3 / 0.00613
C H / 10-31,7-32 / 2 / 2.154 / 0.107 / 2.170(4) / 0.107(4) / 3 / 0.00668
C H / 9-28,2-16,3-18 / 3 / 2.153 / 0.107 / 2.170(4) / 0.107(4) / 3 / 0.00648
C H / 6-20,5-21,11-28 / 3 / 2.155 / 0.107 / 2.172(4) / 0.107(4) / 3 / 0.00652
C H / 12-31 / 1 / 2.156 / 0.107 / 2.172(4) / 0.107(4) / 3 / 0.00672
C H / 10-27 / 1 / 2.157 / 0.107 / 2.173(4) / 0.107(4) / 3 / 0.00649
C H / 4-15 / 1 / 2.158 / 0.106 / 2.174(4) / 0.106(4) / 3 / 0.00677
C H / 8-27,12-30 / 2 / 2.162 / 0.107 / 2.178(4) / 0.107(4) / 3 / 0.00652
C H / 5-22 / 1 / 2.162 / 0.107 / 2.178(4) / 0.107(4) / 3 / 0.00619
C H / 4-19,9-25 / 2 / 2.163 / 0.106 / 2.179(4) / 0.107(4) / 3 / 0.00663
C H / 8-26 / 1 / 2.165 / 0.106 / 2.181(4) / 0.107(4) / 3 / 0.00630
C H / 8-23,9-24 / 2 / 2.166 / 0.107 / 2.182(4) / 0.107(4) / 3 / 0.00617
C H / 11-32 / 1 / 2.168 / 0.107 / 2.185(4) / 0.107(4) / 3 / 0.00676
C H / 3-14 / 1 / 2.169 / 0.107 / 2.186(4) / 0.107(4) / 3 / 0.00621
C H / 11-29 / 1 / 2.170 / 0.106 / 2.186(4) / 0.106(4) / 3 / 0.00603
C H / 10-30 / 1 / 2.172 / 0.106 / 2.188(4) / 0.106(4) / 3 / 0.00599
C H / 10-26 / 1 / 2.172 / 0.106 / 2.189(4) / 0.106(4) / 3 / 0.00606
C H / 3-17 / 1 / 2.174 / 0.106 / 2.190(4) / 0.106(4) / 3 / 0.00638
C H / 9-29 / 1 / 2.174 / 0.106 / 2.191(4) / 0.106(4) / 3 / 0.00598
C H / 4-16,7-33 / 2 / 2.175 / 0.106 / 2.192(4) / 0.106(4) / 3 / 0.00609
C H / 4-20 / 1 / 2.176 / 0.106 / 2.193(4) / 0.106(4) / 3 / 0.00595
C H / 5-17,7-25 / 2 / 2.177 / 0.106 / 2.194(4) / 0.106(4) / 3 / 0.00627
C C / 2-6 / 1 / 2.379 / 0.065 / 2.389(5) / 0.066(4) / 3 / 0.00291
C C / 6-7 / 1 / 2.405 / 0.067 / 2.406(5) / 0.067(4) / 3 / 0.00217
N C / 1-8 / 1 / 2.454 / 0.067 / 2.410(5) / 0.068(4) / 3 / 0.00297
N C / 1-3 / 1 / 2.458 / 0.066 / 2.441(5) / 0.066(4) / 3 / 0.00378
N C / 1-5 / 1 / 2.473 / 0.065 / 2.478(5) / 0.066(4) / 3 / 0.00356
C C / 2-7 / 1 / 2.476 / 0.070 / 2.478(5) / 0.070(4) / 3 / 0.00268
C C / 3-5 / 1 / 2.493 / 0.068 / 2.507(5) / 0.068(4) / 3 / 0.00410
C C / 8-12 / 1 / 2.496 / 0.068 / 2.510(5) / 0.068(4) / 3 / 0.00399
C C / 4-6 / 1 / 2.501 / 0.067 / 2.515(5) / 0.068(4) / 3 / 0.00350
C C / 9-11 / 1 / 2.506 / 0.068 / 2.520(5) / 0.069(4) / 3 / 0.00368
C C / 8-10 / 1 / 2.515 / 0.068 / 2.529(5) / 0.068(4) / 3 / 0.00387
N C / 1-12 / 1 / 2.518 / 0.068 / 2.608(5) / 0.068(4) / 3 / 0.00279
C C / 2-4 / 1 / 2.524 / 0.068 / 2.538(5) / 0.068(4) / 3 / 0.00328
C C / 7-11 / 1 / 2.532 / 0.070 / 2.564(5) / 0.070(4) / 3 / 0.00467
C C / 10-12 / 1 / 2.538 / 0.068 / 2.553(5) / 0.069(4) / 3 / 0.00387
C C / 7-9 / 1 / 2.548 / 0.069 / 2.563(5) / 0.070(4) / 3 / 0.00445
C C / 2-12 / 1 / 2.841 / 0.091 / 2.917(6) / 0.100(4) / 4 / -0.0076
C C / 3-6 / 1 / 2.859 / 0.071 / 2.864(6) / 0.080(4) / 4 / 0.00536
C C / 2-5 / 1 / 2.890 / 0.071 / 2.914(6) / 0.080(4) / 4 / 0.00484
C C / 8-11 / 1 / 2.917 / 0.073 / 2.940(6) / 0.083(4) / 4 / 0.00593
N C / 1-4 / 1 / 2.931 / 0.072 / 2.926(6) / 0.081(4) / 4 / 0.00540
C C / 9-12 / 1 / 2.949 / 0.073 / 2.957(6) / 0.082(4) / 4 / 0.00555
C C / 7-10 / 1 / 2.988 / 0.073 / 3.011(6) / 0.082(4) / 4 / 0.00619
C C / 6-8 / 1 / 3.055 / 0.110 / 3.099(6) / 0.119(4) / 4 / 0.00470
C C / 6-12 / 1 / 3.766 / 0.076 / 3.789(8) / 0.078(7) / 5 / 0.01141
C C / 2-8 / 1 / 3.767 / 0.079 / 3.700(7) / 0.080(7) / 5 / 0.01438
C C / 5-7 / 1 / 3.769 / 0.071 / 3.774(8) / 0.072(7) / 5 / 0.00878
C C / 3-7 / 1 / 3.811 / 0.069 / 3.800(8) / 0.070(7) / 5 / 0.00898
N C / 1-9 / 1 / 3.830 / 0.070 / 3.806(8) / 0.071(7) / 5 / 0.00955
N C / 1-11 / 1 / 3.864 / 0.068 / 3.938(8) / 0.070(7) / 5 / 0.00910
C C / 3-12 / 1 / 4.286 / 0.095 / 4.391(9) / 0.113(8) / 6 / 1.70E-04
C C / 5-8 / 1 / 4.313 / 0.115 / 4.309(9) / 0.133(8) / 6 / 0.01139
C C / 2-11 / 1 / 4.331 / 0.094 / 4.434(9) / 0.111(8) / 6 / 3.00E-05
C C / 4-7 / 1 / 4.336 / 0.075 / 4.344(9) / 0.092(8) / 6 / 0.01161
N C / 1-10 / 1 / 4.347 / 0.078 / 4.379(9) / 0.095(8) / 6 / 0.01249
C C / 6-9 / 1 / 4.399 / 0.108 / 4.402(9) / 0.125(8) / 6 / 0.01043
C C / 3-8 / 1 / 4.866 / 0.117 / 4.754(9) / 0.135(8) / 6 / 0.02231
C C / 6-11 / 1 / 4.918 / 0.103 / 4.928(10) / 0.120(8) / 6 / 0.01800
C C / 5-12 / 1 / 4.981 / 0.079 / 5.058(10) / 0.096(8) / 6 / 0.01534
C C / 2-9 / 1 / 4.996 / 0.078 / 4.984(10) / 0.096(8) / 6 / 0.01689
C C / 2-10 / 1 / 5.190 / 0.096 / 5.220(10) / 0.113(8) / 6 / 0.01227
C C / 4-12 / 1 / 5.212 / 0.090 / 5.291(11) / 0.108(8) / 6 / 0.01066
C C / 4-8 / 1 / 5.244 / 0.101 / 5.204(10) / 0.118(8) / 6 / 0.02182
C C / 6-10 / 1 / 5.272 / 0.091 / 5.294(11) / 0.108(8) / 6 / 0.01988
C C / 5-9 / 1 / 5.761 / 0.115 / 5.730(11) / 0.135(22) / 7 / 0.02219
C C / 3-11 / 1 / 5.805 / 0.095 / 5.916(12) / 0.115(22) / 7 / 0.01155
C C / 3-9 / 1 / 6.251 / 0.098 / 6.190(12) / 0.118(22) / 7 / 0.02875
C C / 5-11 / 1 / 6.277 / 0.087 / 6.325(13) / 0.107(22) / 7 / 0.02596
C C / 3-10 / 1 / 6.554 / 0.116 / 6.567(13) / 0.136(22) / 7 / 0.02425
C C / 5-10 / 1 / 6.620 / 0.102 / 6.647(13) / 0.122(22) / 7 / 0.03022
C C / 4-11 / 1 / 6.646 / 0.097 / 6.728(13) / 0.116(22) / 7 / 0.02195
C C / 4-9 / 1 / 6.673 / 0.096 / 6.650(13) / 0.116(22) / 7 / 0.03072
C C / 4-10 / 1 / 7.273 / 0.093 / 7.303(15) / 0.113(22) / 7 / 0.03233
Conformer IIIAxC-EqN
Atompair / Atom
numbers / Multiply / Theoretical / Experimental[b] / Group
№[c] / ∆r[a]
r / l / r / l
C H / 2-13,6-21 / 2 / 1.091 / 0.076 / 1.102(2) / 0.078(1) / 1 / 0.0012
C H / 8-25,12-33 / 2 / 1.094 / 0.076 / 1.104(2) / 0.078(1) / 1 / 0.00132
C H / 4-17,9-27,11-31 / 3 / 1.096 / 0.076 / 1.106(2) / 0.078(1) / 1 / 0.00129
C H / 3-16,5-20,10-29 / 3 / 1.096 / 0.076 / 1.107(2) / 0.078(1) / 1 / 0.00136
C H / 9-26,10-30,
3-15,5-19 / 4 / 1.097 / 0.077 / 1.107(2) / 0.078(1) / 1 / 0.00131
C H / 8-24,12-32,4-18 / 3 / 1.098 / 0.077 / 1.108(2) / 0.079(1) / 1 / 0.00126
C H / 10-28 / 1 / 1.099 / 0.077 / 1.110(2) / 0.079(1) / 1 / 0.00123
C H / 7-23 / 1 / 1.11 / 0.079 / 1.120(2) / 0.081(1) / 1 / 1.00E-03
C H / 2-14,6-22 / 2 / 1.111 / 0.079 / 1.121(2) / 0.081(1) / 1 / 0.00110
N C / 1-2,1-6 / 2 / 1.466 / 0.049 / 1.465(3) / 0.054(2) / 2 / 0.00105
N C / 1-7 / 1 / 1.476 / 0.050 / 1.475(3) / 0.054(2) / 2 / 4.30E-04
C C / 3-4,4-5 / 2 / 1.526 / 0.050 / 1.533(3) / 0.055(2) / 2 / 1.70E-04
C C / 5-6,2-3 / 2 / 1.528 / 0.050 / 1.535(3) / 0.055(2) / 2 / 5.10E-04
C C / 8-9,11-12 / 2 / 1.532 / 0.051 / 1.539(3) / 0.055(2) / 2 / 5.50E-04
C C / 9-10,10-11 / 2 / 1.533 / 0.051 / 1.540(3) / 0.055(2) / 2 / 5.90E-04
C C / 7-12,7-8 / 2 / 1.539 / 0.051 / 1.546(3) / 0.056(2) / 2 / 4.20E-04
H H / 24-25,32-33 / 2 / 1.751 / 0.123 / 1.755(3) / 0.127(2) / 2 / 0.00833
H H / 28-29 / 1 / 1.765 / 0.123 / 1.769(4) / 0.128(2) / 2 / 0.00815
H H / 17-18 / 1 / 1.768 / 0.123 / 1.773(4) / 0.128(2) / 2 / 0.00788
H H / 26-27,30-31 / 2 / 1.771 / 0.123 / 1.775(4) / 0.128(2) / 2 / 0.00812
H H / 15-16,19-20 / 2 / 1.744 / 0.123 / 1.748(3) / 0.128(2) / 2 / 0.00821
H H / 21-22,13-14 / 2 / 1.776 / 0.123 / 1.809(4) / 0.128(2) / 2 / 0.00763
H H / 21-33 / 1 / 1.963 / 0.223 / 1.995(4) / 0.224(4) / 3 / -0.10686
H H / 13-25 / 1 / 1.959 / 0.223 / 1.842(4) / 0.224(4) / 3 / -0.10665
C C / 2-6 / 1 / 2.387 / 0.067 / 2.398(5) / 0.067(4) / 3 / 0.00353
C C / 2-7,6-7 / 2 / 2.425 / 0.072 / 2.427(5) / 0.072(4) / 3 / 0.00239
C C / 8-12 / 1 / 2.47 / 0.064 / 2.485(5) / 0.064(4) / 3 / 0.00232
N C / 1-3,1-5 / 2 / 2.477 / 0.066 / 2.461(5) / 0.066(4) / 3 / 0.00397
C C / 3-5 / 1 / 2.481 / 0.067 / 2.496(5) / 0.067(4) / 3 / 0.00413
N C / 1-8,1-12 / 2 / 2.488 / 0.067 / 2.445(5) / 0.067(4) / 3 / 0.00300
C C / 4-6,2-4 / 2 / 2.514 / 0.069 / 2.529(5) / 0.069(4) / 3 / 0.00339
C C / 8-10,10-12 / 2 / 2.519 / 0.068 / 2.534(5) / 0.069(4) / 3 / 0.00381
C C / 7-11,7-9 / 2 / 2.527 / 0.066 / 2.559(5) / 0.066(4) / 3 / 0.00344
C C / 9-11 / 1 / 2.539 / 0.069 / 2.553(5) / 0.069(4) / 3 / 0.00381
C C / 3-6,2-5 / 2 / 2.873 / 0.072 / 2.879(6) / 0.081(4) / 4 / 0.00536
C C / 2-8,6-12 / 2 / 2.916 / 0.130 / 2.861(6) / 0.139(4) / 4 / -0.00668
C C / 8-11,9-12 / 2 / 2.935 / 0.073 / 2.958(6) / 0.082(4) / 4 / 0.00471
N C / 1-4 / 1 / 2.945 / 0.070 / 2.940(6) / 0.079(4) / 4 / 0.00579
N C / 1-11,1-9 / 2 / 2.968 / 0.112 / 2.996(6) / 0.121(4) / 4 / 0.00837
C C / 7-10 / 1 / 2.970 / 0.071 / 2.993(6) / 0.081(4) / 4 / 0.00539
C C / 2-9,6-11 / 2 / 3.534 / 0.265 / 3.476(7) / 0.266(7) / 5 / 0.02964
N C / 1-10 / 1 / 3.540 / 0.121 / 3.528(7) / 0.122(7) / 5 / 0.01167
C C / 3-7,5-7 / 2 / 3.792 / 0.070 / 3.783(8) / 0.071(7) / 5 / 0.00932
C C / 2-12,6-8 / 2 / 3.796 / 0.072 / 3.806(8) / 0.073(7) / 5 / 0.02389
C C / 5-12,3-8 / 2 / 4.305 / 0.106 / 4.314(9) / 0.123(8) / 6 / -3.10E-04
C C / 2-11,6-9 / 2 / 4.306 / 0.165 / 4.332(9) / 0.182(8) / 6 / 0.04123
C C / 4-7 / 1 / 4.324 / 0.078 / 4.333(9) / 0.095(8) / 6 / 0.01251
C C / 2-10,6-10 / 2 / 4.548 / 0.233 / 4.527(9) / 0.250(8) / 6 / 0.04083
C C / 5-11,3-9 / 2 / 4.571 / 0.244 / 4.562(9) / 0.261(8) / 6 / 0.01656
C C / 3-12,5-8 / 2 / 4.965 / 0.091 / 4.956(10) / 0.108(8) / 6 / 0.02595
C C / 3-11,5-9 / 2 / 5.215 / 0.216 / 5.196(10) / 0.233(8) / 6 / 0.03849
C C / 4-12,4-8 / 2 / 5.247 / 0.095 / 5.261(10) / 0.112(8) / 6 / 0.01940
C C / 3-10,5-10 / 2 / 5.521 / 0.261 / 5.435(11) / 0.279(8) / 6 / 0.03579
C C / 4-11,4-9 / 2 / 5.595 / 0.184 / 5.586(11) / 0.201(8) / 6 / 0.03406
C C / 4-10 / 1 / 6.264 / 0.202 / 6.195(12) / 0.222(22) / 7 / 0.04231
[a] rh1 values (rh1=ra+Δr) are given for GED results. The vibrational corrections ∆r were calculated by the SHRINK program [5,6] using the so called second approximation, in which harmonic approach with nonlinear relation between Cartesian and internal coordinates were applied on the base of the force field estimated in the quantum chemical calculations at MP2/6-311G** level.
[b] Values in parentheses for the GED data are full errors estimated as (rh1)=[scale2+(2.5LS)2]½, where scale =0.002r and LS is a standard deviation in least-squares refinement for internuclear distances and as 3LS for vibration amplitudes. The place-value is such that the last digit of the uncertainty lines up with the last digit of the nominal value.
[c] All amplitudes were refined being united in 7 groups. The differences between the amplitudes within each group were constrained to the calculated values (see text).
Experimental total intensities and background
I(s) long camera s= 1.2 to 16.4 Å–1; step 0.1 Å–1; λ= 0.04091021 Å, sequence in rows
2.39824 2.06992 1.64980 1.31076 1.06773 0.89526 0.76950 0.67978
0.61757 0.57014 0.53331 0.50475 0.48372 0.47123 0.46956 0.46779
0.46905 0.46560 0.45678 0.44688 0.42544 0.40033 0.37342 0.34759
0.32593 0.30859 0.29745 0.29087 0.28765 0.28688 0.28862 0.29144
0.29615 0.30365 0.31295 0.32393 0.33682 0.34875 0.36096 0.37091
0.37738 0.38054 0.37982 0.37561 0.36824 0.35856 0.34862 0.33656
0.32539 0.31278 0.30088 0.28946 0.27828 0.26834 0.25850 0.25111
0.24405 0.23886 0.23468 0.23166 0.22866 0.22775 0.22638 0.22672
0.22628 0.22680 0.22723 0.22759 0.22851 0.23016 0.23224 0.23490
0.23767 0.23992 0.24158 0.24236 0.24101 0.23880 0.23617 0.23203
0.22840 0.22479 0.22165 0.21918 0.21696 0.21568 0.21413 0.21283
0.21175 0.21031 0.20845 0.20713 0.20505 0.20291 0.20058 0.19819
0.19564 0.19350 0.19097 0.18958 0.18844 0.18798 0.18748 0.18745
0.18813 0.18864 0.18972 0.19031 0.19157 0.19308 0.19460 0.19666
0.19948 0.20176 0.20506 0.20785 0.21110 0.21404 0.21615 0.21816
0.21818 0.21776 0.21596 0.21343 0.21099 0.20746 0.20404 0.20083
0.19853 0.19583 0.19371 0.19217 0.19122 0.19044 0.19076 0.19087
0.19132 0.19235 0.19318 0.19410 0.19533 0.19618 0.19699 0.19766
0.19773 0.19776 0.19810 0.19890 0.19905 0.19913 0.19977 0.20022
0.20076
I(s) short camera s= 2.6 to 29.2 Å–1; step 0.1 Å–1; λ= 0.04045707 Å, sequence in rows
4.12959 4.13549 4.04938 3.96396 3.84602 3.67190 3.40815 3.12047
2.81811 2.54159 2.30319 2.12016 1.96641 1.84613 1.75610 1.68770
1.63139 1.58479 1.54691 1.53099 1.52111 1.51831 1.52080 1.51238
1.51520 1.50285 1.47868 1.44974 1.41098 1.36373 1.31524 1.25371
1.18908 1.12469 1.06669 1.00374 0.94616 0.89049 0.84036 0.79084
0.74979 0.71156 0.67885 0.65313 0.63098 0.61283 0.59789 0.58614
0.57723 0.56981 0.56230 0.55564 0.54932 0.54506 0.54247 0.54002
0.53912 0.54063 0.53958 0.54222 0.54072 0.53673 0.53167 0.52476
0.51429 0.50396 0.49178 0.48037 0.47096 0.46183 0.45395 0.44725
0.44112 0.43624 0.43062 0.42495 0.41811 0.41217 0.40553 0.39963
0.39325 0.38685 0.38053 0.37347 0.36787 0.36212 0.35879 0.35533
0.35319 0.35120 0.35033 0.34912 0.34729 0.34835 0.34937 0.34980
0.35062 0.35335 0.35577 0.36036 0.36346 0.36810 0.37307 0.37742
0.38129 0.38292 0.38286 0.38122 0.37779 0.37308 0.36620 0.35922
0.35077 0.34433 0.33731 0.33108 0.32602 0.32195 0.31748 0.31520
0.31406 0.31274 0.31236 0.31265 0.31313 0.31453 0.31499 0.31398
0.31448 0.31395 0.31361 0.31306 0.31151 0.31088 0.31014 0.30956
0.30853 0.30820 0.30826 0.30907 0.30938 0.31022 0.31127 0.31308
0.31489 0.31602 0.31745 0.31916 0.32077 0.32241 0.32337 0.32507
0.32544 0.32570 0.32599 0.32475 0.32311 0.32085 0.31911 0.31689
0.31428 0.31117 0.30902 0.30572 0.30364 0.30186 0.30073 0.29907
0.29833 0.29849 0.29884 0.29950 0.29964 0.30073 0.30185 0.30346
0.30521 0.30687 0.30762 0.30911 0.30996 0.31068 0.31164 0.31209
0.31250 0.31363 0.31399 0.31411 0.31488 0.31636 0.31560 0.31661
0.31687 0.31600 0.31665 0.31656 0.31589 0.31549 0.31541 0.31538
0.31405 0.31426 0.31414 0.31432 0.31454 0.31400 0.31380 0.31393
0.31459 0.31382 0.31360 0.31326 0.31298 0.31230 0.31320 0.31302
0.31284 0.31370 0.31411 0.31404 0.31477 0.31519 0.31547 0.31512
0.31573 0.31620 0.31621 0.31691 0.31683 0.31720 0.31631 0.31604
0.31575 0.31587 0.31507 0.31433 0.31327 0.31252 0.31182 0.31134
0.31063 0.30971 0.30886 0.30834 0.30760 0.30754 0.30713 0.30633
0.30549 0.30536 0.30545 0.30526 0.30508 0.30521 0.30494 0.30453
0.30450 0.30509 0.30465 0.30441 0.30409 0.30412 0.30415 0.30349
0.30327 0.30259 0.30281
Background G(s) long camera, sequence in rows
1.84565 1.70354 1.48475 1.29305 1.13968 1.01798 0.91706 0.83310
0.76877 0.71558 0.66989 0.62969 0.59449 0.56305 0.53447 0.50984
0.48731 0.46815 0.45142 0.43807 0.42707 0.41670 0.40727 0.39882
0.39116 0.38464 0.37910 0.37377 0.36920 0.36473 0.36064 0.35659
0.35274 0.34893 0.34490 0.34114 0.33755 0.33395 0.33025 0.32646
0.32273 0.31892 0.31493 0.31112 0.30725 0.30329 0.29949 0.29589
0.29212 0.28836 0.28470 0.28122 0.27764 0.27432 0.27107 0.26780
0.26467 0.26153 0.25839 0.25516 0.25227 0.24954 0.24691 0.24452
0.24215 0.24001 0.23788 0.23584 0.23425 0.23255 0.23104 0.22954
0.22814 0.22686 0.22536 0.22393 0.22255 0.22121 0.21998 0.21881
0.21766 0.21640 0.21538 0.21446 0.21358 0.21270 0.21190 0.21112
0.21036 0.20964 0.20893 0.20825 0.20760 0.20689 0.20619 0.20561
0.20507 0.20446 0.20397 0.20351 0.20307 0.20266 0.20228 0.20191
0.20156 0.20122 0.20089 0.20057 0.20026 0.19995 0.19966 0.19936
0.19905 0.19872 0.19842 0.19812 0.19781 0.19752 0.19723 0.19695
0.19667 0.19641 0.19618 0.19600 0.19592 0.19592 0.19599 0.19622
0.19653 0.19688 0.19725 0.19762 0.19803 0.19843 0.19886 0.19924
0.19964 0.20002 0.20035 0.20068 0.20107 0.20145 0.20188 0.20228
0.20270 0.20311 0.20360 0.20409 0.20460 0.20505 0.20554 0.20600
0.20641
Background G(s) short camera, sequence in rows
4.70519 4.46574 4.22715 4.00212 3.79317 3.60211 3.42163 3.24110
3.07138 2.91082 2.75857 2.62850 2.48885 2.36221 2.24432 2.13581
2.03395 1.93381 1.83962 1.75442 1.67120 1.59608 1.52133 1.45275
1.38625 1.32894 1.27518 1.22499 1.17772 1.13800 1.09941 1.06035
1.02483 0.98935 0.95570 0.92338 0.89289 0.86371 0.83606 0.80901
0.78262 0.75769 0.73421 0.71391 0.69343 0.67449 0.65770 0.64219
0.62780 0.61445 0.60043 0.58742 0.57605 0.56465 0.55470 0.54515
0.53598 0.52722 0.51910 0.51211 0.50496 0.49811 0.49162 0.48559
0.47976 0.47385 0.46812 0.46255 0.45713 0.45186 0.44674 0.44177
0.43690 0.43220 0.42765 0.42328 0.41905 0.41498 0.41108 0.40733
0.40386 0.40056 0.39721 0.39398 0.39112 0.38838 0.38526 0.38251
0.37965 0.37688 0.37431 0.37149 0.36891 0.36652 0.36435 0.36226
0.36025 0.35837 0.35670 0.35505 0.35347 0.35186 0.35044 0.34900
0.34769 0.34627 0.34488 0.34345 0.34238 0.34109 0.33978 0.33850
0.33710 0.33582 0.33454 0.33326 0.33212 0.33103 0.32991 0.32889
0.32799 0.32710 0.32624 0.32557 0.32476 0.32411 0.32341 0.32272
0.32204 0.32140 0.32092 0.32033 0.31975 0.31921 0.31869 0.31811
0.31762 0.31707 0.31661 0.31607 0.31554 0.31492 0.31449 0.31402
0.31371 0.31324 0.31282 0.31249 0.31223 0.31188 0.31163 0.31140
0.31119 0.31088 0.31074 0.31051 0.31029 0.31011 0.30990 0.30972
0.30952 0.30943 0.30924 0.30908 0.30896 0.30888 0.30875 0.30865
0.30862 0.30857 0.30858 0.30857 0.30858 0.30860 0.30864 0.30867
0.30874 0.30881 0.30891 0.30902 0.30917 0.30930 0.30955 0.30980
0.31005 0.31040 0.31074 0.31106 0.31136 0.31167 0.31198 0.31229
0.31257 0.31287 0.31315 0.31343 0.31368 0.31392 0.31415 0.31438
0.31458 0.31478 0.31498 0.31510 0.31531 0.31548 0.31563 0.31569
0.31581 0.31589 0.31598 0.31603 0.31607 0.31610 0.31609 0.31599
0.31603 0.31594 0.31583 0.31569 0.31552 0.31532 0.31508 0.31481
0.31453 0.31425 0.31396 0.31367 0.31337 0.31307 0.31279 0.31250
0.31222 0.31194 0.31166 0.31139 0.31125 0.31104 0.31084 0.31066
0.31040 0.31015 0.30990 0.30965 0.30940 0.30916 0.30885 0.30861
0.30837 0.30813 0.30789 0.30764 0.30738 0.30711 0.30670 0.30640
0.30612 0.30584 0.30553 0.30520 0.30475 0.30443 0.30398 0.30345
0.30292 0.30247 0.30213
1
[1]G. V. Girichev, A. N. Utkin and Y. F. Revichev, Prib. Tekh. Eksp., 1984, 2, 187-190
[2]G. V. Girichev, S. A. Shlykov, V. N. Petrova, N. Y. Subbotyina, S. B. Lapshina and T. G. Danilova, Izv. Vyssh. Uchebn. Zaved., Khim. Khim. Tekhnol., 1988, 31, 46-49
[3]E. G. Girichev, A. V. Zakharov, G. V. Girichev, M. I. Bazanov, Izv. Vyssh. Uchebn. Zaved.,
Tekhnol. Tekst., Promsti 2000, 2, 1 42-1 46
[4]B. Andersen, H. M. Seip, T. G. Strand, R. Stølevik, Acta Chem. Scand. 1969, 23, 3224–3234
[5]Sipachev, V. A. "Calculation of shrinkage corrections in harmonic approximation." Journal of Molecular Structure: THEOCHEM 121 (1985): 143-151
[6]Sipachev, V. A. "Local centrifugal distortions caused by internal motions of molecules." Journal of Molecular Structure 567 (2001): 67-72.