Electronic Supplementary Material
The influence of CH bond polarization on the self-association of 2-acylaminopyrimidines by NH/CH···O/N interactions: XRD, NMR, DFT and AIM study
Borys Ośmiałowski*a, Erkki Kolehmainenb, Arto Valkonenb, Magdalena Kowalskab, Satu Ikonena
aUniversity of Technology and Life Sciences, Faculty of Technology and Chemical Engineering, Seminaryjna 3, PL-85-326 Bydgoszcz, Poland,
bDepartment of Chemistry, University of Jyväskylä, P.O. Box 35, FI-40014 Finland,
Synthesis and compound characterization2
NMR Spectroscopy2
X-ray crystallography3
Crystallographic Data 3
QTAIM based data7
NMR spectra8
Optimized structures (Cartesians)10
CIF files27
References44
Experimental procedures
Synthesis and compound characterization
All compounds were synthesized as described earlier for 2-acylaminopyridines.[1] The substrates for synthesis were purchased from Aldrich and were used as received. For each synthesis 500mg of 2-aminopyrimidine was used. The melting points were determined with the use of Büchi apparatus with 5°C/min. gradient. Compounds were purified by recrystalization from hexane/ethyl acetate mixture (10:1 v:v). Crystals suitable for X-ray determination were obtained during slow evaporation of solutions used in NMR experiments1. Yield 738mg (85%). Mp 125.4-126.9°C. Anal. Calc: C, 58.17; H, 6.71; N, 25.44, Found: C 58.15, H 6.73, N 25.40. 1H NMR (CDCl3) : 9.09 (bs, 1H, H7), 8.61 (d, 2H, H4 and H6, 3JH,H=4.9 Hz), 6.97 (t, 1H, H5, 3JH,H=4.9 Hz), 3.12 (m, 1H, methine CH, 3JH,H= 6.9 Hz), 1.23 (d, 6H, CH3, 3JH,H= 6.9 Hz), 13C NMR: 176.8 (C8), 158.3 (C4 and C6), 157.7 (C2), 116.1 (C5), 35.5 (methine CH), 19.1 (CH3), 15N NMR: -118.4 (N1 and N3), -238.4 (N7). 2. Yield 856mg (79%). Mp 167.0-169.1°C. Anal. Calc: C, 34.98; H, 2.45; N, 20.40; Found: C 34.95, H 2.49, N 20.34. 1H NMR (CDCl3) : 9.29 (bs, 1H, H7), 8.71 (d, 2H, H4 and H6, 3JH,H= 4.9 Hz), 7.12 (t, 1H, H5,3JH,H= 4.9 Hz), 6.65 (bs, 1H, CHCl2), 13C NMR: 158.6 (C4 and C6), 156.6 (C2), 117.5 (C5), 66.5 (CHCl2), C8 not observed 15N NMR: -117.9 (N1 and N3), -254.7 (N7
NMR Spectroscopy
1H and 15N NMR spectra in CDCl3-solution at 303 K were recorded with a Bruker Avance DRX500 spectrometer equipped with a 5 mm diameter broad band inverse detection probe head and z-gradient working at 500.13 MHz for 1H and at 50.68 MHz for 15N, respectively. 13C NMR spectra in CDCl3-solution at 303 K were recorded with a Bruker Avance DRX500 spectrometer equipped with a 5 mm diameter direct detection probe head working at 500.13 MHz for 1H, and at 125.76 MHz for 13C, respectively. A composite pulse decoupling, Waltz-16, was used to remove proton couplings from 13C spectra. The 1H and 13C NMR chemical shifts are referenced to an internal TMS ( = 0.00 ppm) and 15N shifts to an external nitromethane ( = 0.0 ppm) in a capillary inserted coaxially inside the NMR tube. The 15N chemical shifts are observed by PFG 1H, 15N HMBC technique using 100 ms evolution delay for proton-nitrogen-15 spin-spin couplings.
X-ray crystallography
Data were collected at 123(2) K on a Bruker-Nonius KappaCCD diffractometer with ApexII detector using graphite monochromated Mo-Kα radiation. COLLECT[2] data collection software was utilized for data collection and data were processed with DENZO-SMN[3]. Data collected from the crystals of 2 was corrected for absorption effects using SADABS[4]. The structures were solved by direct methods (SIR2002[5]) and refined anisotropically by full matrix least squares on F2 values utilizing SHELXL-97[6]. In the case of 1, the crystal was found to be non-merohedral twin. Two domain hklf5-file was created and used with BASF and HKLF 5 instructions in the final data refinements. Hydrogen atoms bound to carbons were positioned according to the expected geometry and were refined only isotropically riding on the parent atom. Hydrogen atoms bound to nitrogen were located from the electron density map and refined isotropically. Figures were drawn with Ortep-3 for Windows[7] and Mercury[8].
Crystallographic Data
Table S1. Crystal data and structure refinement parameters
1 / 2Empirical formula / C8H11N3O / C6H5Cl2N3O
Molecular weight (gmol-1) / 165.20 / 206.03
Crystal system / Monoclinic / Tetragonal
Space group / P21 / P41212
a (Å) / 9.2358(5) / 9.7577(2)
b (Å) / 10.2925(6) / 9.7577(2)
c (Å) / 9.3974(6) / 18.0008(5)
(o) / 90 / 90
(o) / 90.847(3) / 90
(o) / 90 / 90
Volume (Å3) / 893.21(9) / 1713.90(7)
Z / 4 / 8
Densitycalc (gcm-3) / 1.228 / 1.597
T / K / 123(2) / 123(2)
Abs. coefficient (mm-1) / 0.085 / 0.709
F(0 0 0) / 352 / 832
range (o) / 3.65-25.24 / 3.16-28.29
Index ranges (o) / -11h11
-12k12
-11l11 / -12h12
-13k11
-20l23
Reflections collected / 2920 / 13822
Internal consistency / - / 0.0412
Data/restraints/parameters / 2920 / 1 / 229 / 2099 / 0 / 112
Goodness-of-fit on F2 / 1.174 / 1.068
Final R indices [I2σ(I)] / 0.0510 / 0.0428
wR indices (all data) / 0.1407 / 0.0859
Largest diffraction peak and hole (eÅ−3) / 0.233 and -0.228 / 0.289 and -0.458
Extinction coefficient / 0.073(16) / -
Flack parameter / -1(3)* / 0.09(9)
*absolute structure parameter is meaningless and removed from the data
Fig. S1 Structure of 1 and 2 (bottom view along N–H bond)
Table S2. Selected dihedral angles in acylamino groups in 1 and 2 [°]
Dihedral angle / 1 / 2N(7)C(8)C(10)C(11) / A -141.2(3)
B -118.0(4)
N(7)C(8)C(10)Cl(11) / -128.53(17)
N(7)C(8)C(10)C(12) / A 96.6(4)
B 119.8(4)
N(7)C(8)C(10)Cl(12) / 110.91(19)
C(2)N(7)C(8)C(10) / A -173.3(3)
B 176.7(3) / -178.8(2)
A and B refer to two crystallographically independent molecules in asymmetric unit of 1.
Table S3. Chosen geometry parameters in 1 and 2 [Å]
Parameter / 1 / 2P1
(angle between rings) / 61a / 90b
D1c / 5.432, 5.498 / 6.143
T1d (N7N3'O9') / 3.864, 4.010 / 3.748
T2d (C10N3'O9') / 4.392, 4.534 / 4.226
T3d (N7O9'C10) / 3.711, 3.682 / 3.385
T4d (N7N3'C10) / 3.640, 3.843 / 3.624
a – the planes determined by first and third molecule's ring in the ribbon-like structure are parallel, b – molecules in 2 are arranged around four-fold axis, c – the distance between ring centroids, d – area of triangle in Å2.
1H and 13C NMR spectra
Compound 1
Compound 2
Cartesian coordinates for optimized structures
1- monomer open rotamer
C -0.0546651011 -0.0775232862 0.020206633
C 0.0116545461 0.2578390981 2.2525226092
H 0.6042352723 0.439328659 3.1459515539
C -1.3709498351 0.1519047731 2.3222288917
H -1.909437956 0.2433765939 3.2558273954
C -2.0152319935 -0.0764016349 1.11634649
H -3.097904225 -0.1693480812 1.0737756518
C 0.3412733704 -0.4580780624 -2.4451182395
C 1.5275108016 -0.5288265099 -3.4024307291
H 2.4241549547 -0.1500297772 -2.9005142491
C 1.2586632323 0.3339335848 -4.6294157669
H 2.0916089799 0.2630622694 -5.332894807
H 1.1327495546 1.3854374549 -4.3589435912
H 0.3495590629 0.0040677406 -5.136034728
C 1.7676267719 -1.9915691504 -3.7756084435
H 1.9875305615 -2.6007428766 -2.8949201577
H 2.6132250583 -2.0739216539 -4.4625590845
H 0.8852631384 -2.4092044339 -4.2663551705
N 0.7098090286 -0.1846342128 -1.1359505347
H 1.69195256 -0.0575876421 -0.9527757406
N 0.6850048403 0.1464437775 1.1144523364
N -1.3759312875 -0.1929566153 -0.045460246
O -0.794516937 -0.6482131825 -2.8077357613
1- monomer closed rotamer
C -0.0868028593 -0.0886905301 0.1363014272
C 0.1393823436 -0.0593484295 2.3838166228
H 0.7961430813 0.0264142839 3.2470958021
C -1.2298413434 -0.2383017231 2.5438122938
H -1.6946033032 -0.2996877768 3.5187297427
C -1.9575376139 -0.3359442737 1.3694165794
H -3.0358370516 -0.4791852796 1.3904157257
C 0.2230874262 0.018092697 -2.4239671018
C -1.2222939614 -0.1917756095 -2.8229129966
H -1.8619077158 0.2681454818 -2.0689091489
C -1.5157057811 -1.6950740195 -2.8211514513
H -2.5500227646 -1.8718841081 -3.1261510965
H -1.3825010609 -2.1301485722 -1.8291964382
H -0.8614603573 -2.2181079232 -3.5244744946
C -1.485115975 0.4341664829 -4.1847060027
H -1.3077944705 1.5120410864 -4.1690383616
H -2.523931319 0.2652976492 -4.4793356719
H -0.8311839991 0.0058584199 -4.9459973182
N 0.5826492422 -0.0015190158 -1.0688271787
H 1.5771117537 0.1244333372 -0.9482189834
N 0.7248641 0.0184239156 1.1992445771
N -1.4065150183 -0.2668042021 0.161595171
O 1.1129159977 0.1718683356 -3.2274222842
1- dimer D1
C -0.2133720717 -0.7240586267 0.0654572398
C -0.3995622213 -1.4581531696 2.2045699122
H 0.0900563595 -1.7236704224 3.1386092012
C -1.7741939961 -1.5595910049 2.0681897458
H -2.4089496934 -1.8995878829 2.874910562
C -2.2799365241 -1.1995015756 0.8273344969
H -3.3480063189 -1.2497464897 0.6283198689
C 0.3684620175 0.3940545899 -2.0895202671
C 1.5517283397 0.4918477886 -3.0462377028
H 2.4780764159 0.4076459161 -2.4691305016
C 1.5471445524 1.8255123918 -3.7771157874
H 2.3780413319 1.8729965491 -4.4850174574
H 1.6474648539 2.6617056718 -3.0808736188
H 0.6143254318 1.9600638148 -4.3280223406
C 1.4830072336 -0.690553913 -4.0170243246
H 1.4947192344 -1.6491907 -3.4912042919
H 2.3337784526 -0.6685172236 -4.7025618906
H 0.5667984476 -0.6456796688 -4.6119702073
N 0.6536781685 -0.3380435276 -0.9436107394
H 1.626896147 -0.593170219 -0.7750391056
N 0.3920028254 -1.0316820546 1.2245192231
N -1.5181407357 -0.7940322828 -0.182883821
O -0.7069973867 0.8888898155 -2.3276342253
C 4.2000703707 -0.9820327924 0.7131396415
C 4.2819063783 -1.8002483344 -1.4025361945
H 3.7560372912 -2.0354251162 -2.3251586188
C 5.6388769167 -2.0464420339 -1.2725987595
H 6.2244068982 -2.479422839 -2.0721503691
C 6.19477271 -1.7007322237 -0.0492291908
H 7.2538238165 -1.857628783 0.1424712062
C 3.7574378396 0.3179449209 2.7973051919
C 2.5665167856 0.7426833709 3.6512383873
H 1.8370973989 -0.0738476911 3.6499485517
C 2.9987367505 1.0133203258 5.0835728507
H 3.4275503115 0.1215689294 5.5465146118
H 2.1420376407 1.3300868302 5.6831831177
H 3.7543382142 1.8005206774 5.1169187938
C 1.9079020984 1.9690316985 3.0129369973
H 1.0481109396 2.287621237 3.6071215828
H 1.5560988972 1.7627166453 1.9991422449
H 2.6140529701 2.8028106689 2.966331931
N 3.3909167682 -0.4738678356 1.7160638801
H 2.393963219 -0.6225694814 1.5574500781
N 3.5526264891 -1.2597937414 -0.4303938066
N 5.4926774294 -1.1827222523 0.9527098233
O 4.8871544527 0.6821819053 3.0196933402
1 dimer D2
C 2.1312562439 -0.9135764603 -1.0267937739
C 2.4148173416 -1.8883722981 -3.0398934941
H 2.985154797 -1.958716274 -3.9635449408
C 1.3090501516 -2.6987446409 -2.8188839313
H 0.9696080232 -3.4225588776 -3.5477900613
C 0.6692100653 -2.5187385818 -1.6024926404
H -0.207765909 -3.1070887795 -1.3386027847
C 2.1250880363 0.4913346274 1.0662781044
C 2.9144626156 1.6624015771 1.6397753407
H 3.9462485145 1.6064349613 1.2724003239
C 2.9311153972 1.6049906348 3.1596006596
H 3.4712713686 2.4633708002 3.5659113227
H 3.416856366 0.6954395532 3.521031146
H 1.9132785505 1.616398786 3.5524779796
C 2.2887226774 2.9612489275 1.1231622031
H 2.3035467951 3.0129067182 0.0314290042
H 2.8336610649 3.8240497872 1.5137370528
H 1.2465295626 3.035550392 1.4419544168
N 2.6222382168 0.0415542973 -0.1448927306
H 3.4325263327 0.5106627089 -0.5158236065
N 2.8388154674 -0.992247068 -2.1595086261
N 1.0697428787 -1.63671919 -0.6925609553
O 1.1455967058 0.0396654039 1.6120154625
C -1.7044675055 1.0162311475 -0.5760518506
C -0.692836741 2.6972283377 -1.7050326219
H 0.2261963019 3.2264767021 -1.9545783861
C -1.9112039082 3.1050488648 -2.2306331725
H -1.9988573944 3.9496830908 -2.9014722002
C -3.0086486091 2.3553537669 -1.8299512869
H -4.0087309723 2.6010568292 -2.1838288637
C -2.4238272222 -1.0079175314 0.7306691967
C -1.7778571037 -1.980796589 1.7169707813
H -0.7338769167 -2.1291241315 1.4206364421
C -1.7798018292 -1.3467171822 3.1105734132
H -1.1888670365 -0.4285639568 3.132163169
H -1.3478038265 -2.0374534613 3.8395888902
H -2.8007958116 -1.1141195695 3.4276974388
C -2.5076116631 -3.3143201952 1.6985562594
H -2.0665103368 -4.001483045 2.4254539483
H -2.4575395371 -3.7848464888 0.7125608905
H -3.5637145752 -3.1795489065 1.9393133634
N -1.5189970922 -0.0492143635 0.2777473198
H -0.5559126145 -0.1636372875 0.5754724322
N -0.5650072622 1.6643024 -0.8854138307
N -2.9280214181 1.3179776354 -1.0083102167
O -3.5828351885 -1.0644830691 0.4101784139
1 dimer D3
C 0.0434619191 -0.0818956208 -0.0647046005
C 0.032748489 -0.2340772268 2.1925446546
H 0.5980653671 -0.261839676 3.1209742674
C -1.3530931172 -0.3175164527 2.2016056786
H -1.9192184584 -0.4129728226 3.1179369637
C -1.9611072204 -0.263403412 0.9588456181
H -3.0428987466 -0.3154868052 0.8634058157
C 0.5950686992 0.0357388644 -2.5526269245
C -0.8121009468 -0.0777767942 -3.0948003632
H -1.4001343695 -0.6809109163 -2.4037319892
C -0.8080428209 -0.7258918704 -4.4719634898
H -1.8335090366 -0.8165080981 -4.838516386
H -0.3708325631 -1.7269369898 -4.4424427663
H -0.2372604045 -0.1332919503 -5.1892650392
C -1.4320430467 1.3229313426 -3.1286278854
H -1.4939277874 1.7580641668 -2.129732518
H -2.4450867757 1.268770344 -3.5344787962
H -0.8465436122 1.9906891669 -3.767031097
N 0.8403984618 0.0408628366 -1.1935646714
H 1.8389279018 0.1195390086 -0.9764844176
N 0.7434325383 -0.1185907927 1.0782784735
N -1.2808090484 -0.1416237382 -0.1784135184
O 1.5542549655 0.1536382562 -3.3030027874
C 4.8490591533 0.3743544699 -1.509545384
C 4.1585024702 0.2643367405 0.65355077
H 3.3227192138 0.1781810101 1.3437892698
C 5.471205693 0.3581449711 1.0920213664
H 5.7295179529 0.3509966209 2.1423291771
C 6.4282225779 0.4661604928 0.0942686278
H 7.4832234712 0.55074801 0.3452951132
C 5.1989614663 0.3496278836 -3.9967304452
C 4.3323641178 0.3126213321 -5.2532384766
H 3.4053908096 0.8577136631 -5.0511225372
C 5.0534539436 0.9654252423 -6.4219201325
H 5.2726564448 2.0166179863 -6.2189423789
H 4.435851079 0.9158738166 -7.3219992518
H 6.0008831114 0.4618814987 -6.6238819864
C 3.9587348523 -1.1417585902 -5.5524803176
H 3.344841636 -1.1936756572 -6.4550292514
H 3.3861480223 -1.5855176953 -4.7348670917
H 4.8556282877 -1.7461771636 -5.7166577811
N 4.443221333 0.3827663277 -2.8311637156
H 3.4318025627 0.3454439203 -2.9445544116
N 3.8334757045 0.2704679887 -0.6344005777
N 6.1392866598 0.4787172208 -1.2034174113
O 6.406086032 0.3165036413 -4.0309602841
1 dimer D4
C -0.1835760732 -0.0607333621 0.1873030613
C -0.0781726281 0.1615578052 2.4343656094
H 0.5334419705 0.3026282685 3.3225021307
C -1.4593361607 0.0440066518 2.5322830586
H -1.9770083591 0.0873816321 3.4808414523
C -2.1277902067 -0.1287544494 1.3321376231
H -3.2104373034 -0.2279897487 1.3054125705
C 0.2521858268 -0.335373246 -2.3141639729
C -1.1796129003 -0.5356468532 -2.7627967737
H -1.723256245 -1.043563852 -1.9667177658
C -1.2300090939 -1.3662445987 -4.0369314631
H -2.268341282 -1.5014466988 -4.3495589128
H -0.7907412124 -2.3553880625 -3.8864554548
H -0.6837161818 -0.8806619506 -4.8473605197
C -1.8234127656 0.8409096957 -2.9559637188
H -1.8383477274 1.4106530501 -2.0252751521
H -2.8559420422 0.7229394863 -3.2933405371
H -1.2836379397 1.4186055309 -3.7119204606
N 0.5561799783 -0.0998260353 -0.9857520781
H 1.5552069908 0.0532818788 -0.8337550962
N 0.5721994638 0.1089503208 1.2806566268
N -1.5090355622 -0.179370508 0.1548379366
O 1.1706917202 -0.3436281061 -3.118937793
C 4.8662830766 -0.3417143922 -3.9397472267
C 4.8143988109 -0.7971534711 -6.1529364495
H 4.2219803639 -0.9702066528 -7.0483314879
C 6.2025969704 -0.837007506 -6.1989952201
H 6.7446122036 -1.037990056 -7.1130438187
C 6.8445207129 -0.6063055771 -4.9941015159
H 7.9298349313 -0.6196315997 -4.9282408755
C 4.3832043424 0.271741754 -1.5099830334
C 5.8113984407 0.4788370813 -1.0530342553
H 6.402812565 0.8208608304 -1.9015552838
C 5.8701667426 1.5092837691 0.0658437842
H 5.4932093632 2.4802338232 -0.2651696007
H 6.9048158006 1.6427553765 0.3912442665
H 5.2741370176 1.1959265797 0.9247344239
C 6.3759714552 -0.8739710782 -0.6092557702
H 7.4052383886 -0.7511289512 -0.2635980907
H 6.3813888615 -1.5936599269 -1.4297405452
H 5.7875955289 -1.2862583789 0.2154594631
N 4.0972792472 -0.1005629442 -2.8103909981
H 3.093448738 -0.185008508 -2.9824422093
N 4.1343033903 -0.5497522875 -5.0423380947
N 6.1948814761 -0.3641282946 -3.8580553431
O 3.4498700083 0.4065389481 -0.733909672
1 dimer D5
C -0.2587964147 -0.1201898476 0.1291819912
C -0.1724166857 0.3048748383 2.3617891406
H 0.4520451319 0.4655378706 3.2372275446
C -1.5589454797 0.3372974928 2.4247899152
H -2.088812718 0.5226125505 3.3490140812
C -2.2180090954 0.1201704365 1.225997088
H -3.304436612 0.1294744953 1.1783984528
C 0.1991290804 -0.6410801162 -2.3343567728
C -1.238010757 -0.7063641357 -2.8074234151
H -1.8504578945 -1.0993411248 -1.9958615467
C -1.360227822 -1.6055208015 -4.0289579225
H -2.4033530077 -1.6509984219 -4.3518146519
H -1.0299645711 -2.6239447863 -3.8103265639
H -0.7580252081 -1.2319466651 -4.8592344199
C -1.7195135173 0.7178800542 -3.1008439015
H -1.6850557737 1.345409914 -2.2086164446
H -2.75342981 0.6947052329 -3.4536738083
H -1.1064011441 1.1816501434 -3.8792070293
N 0.4935566105 -0.3457118451 -1.0084906665
H 1.5020215472 -0.314443752 -0.8352615165
N 0.4842680768 0.0764457048 1.2302798298
N -1.5882145777 -0.1048225821 0.0754154021
O 1.1348267519 -0.8102869678 -3.0942036898
C 4.2526718641 -0.0922731057 0.496019175
C 4.16629225 -0.5173320856 -1.7365889904
H 3.5418304239 -0.6779825221 -2.6120296783
C 5.5528206745 -0.5497806703 -1.7995849715
H 6.082687724 -0.7351041715 -2.723807552
C 6.211884147 -0.3326688538 -0.6007893205
H 7.2983114085 -0.3419939802 -0.5531867948
C 3.7947477928 0.4286199789 2.9595576058
C 5.2318873998 0.493868949 3.4326299452
H 5.8443464772 0.8868355647 2.6210721822
C 5.3541209474 1.3930166702 4.6541691963
H 5.0238828429 2.4114496125 4.4355414628
H 6.3972459403 1.4384677965 4.9770302732
H 4.7519059879 1.0194526179 5.4844411726
C 5.7133562522 -0.9303880024 3.7260452648
H 6.7472709486 -0.9072385727 4.0788813348
H 5.6788895502 -1.5579120651 2.8338140476
H 5.1002287689 -1.3941483589 4.5044022389
N 3.5003190357 0.1332613302 1.6336895606
H 2.4918538316 0.1020124229 1.460456931
N 3.5096077394 -0.2888926454 -0.6050816773
N 5.582089635 -0.1076661039 0.5497905662
O 2.8590509336 0.5978475276 3.7194009432
1 dimer D6
C -0.1292871242 -0.0826495347 0.2099684089
C -0.0547429166 0.2573182419 2.4468087251
H 0.5462966 0.3909413486 3.3432745905
C -1.441617566 0.2754973042 2.5125346655
H -1.9734771328 0.4205518848 3.4428811828
C -2.0963895212 0.0992058382 1.3051637879
H -3.1825311107 0.100850906 1.2540085917
C 0.3249588844 -0.5337062374 -2.2634002783
C -1.1091059056 -0.6268921076 -2.737578444
H -1.7126934046 -1.0415701555 -1.9305395099
C -1.2089645733 -1.5149840789 -3.9692722693
H -2.2488498437 -1.5714030343 -4.300169529
H -0.8657880866 -2.5307484996 -3.7584354183
H -0.6046168629 -1.1244710737 -4.7896930139
C -1.6211454295 0.7900244778 -3.0158361602
H -1.6049553924 1.4064503797 -2.115268005
H -2.6525480729 0.7467677131 -3.3736752145
H -1.0157267716 1.2767270212 -3.7859222314
N 0.6231099725 -0.2604324196 -0.9384331304
H 1.632994662 -0.213516269 -0.7770644399
N 0.6142975519 0.0793392698 1.3155078831
N -1.4592018671 -0.0763090649 0.1506966362
O 1.2596205828 -0.6653646039 -3.0365915733
C 4.6385828815 -0.1719259072 -1.4625719444
C 3.9878729687 0.1379917038 0.6948079553
H 3.1614365565 0.1970329412 1.3994497682
C 5.3083198746 0.2987780775 1.0910367707
H 5.5829478178 0.4886911958 2.1195712684
C 6.2494515251 0.2041301653 0.0791130888
H 7.3097056088 0.3196864962 0.2920171396
C 4.8554718615 -0.6270085254 -3.972848928
C 6.3627805307 -0.5107997539 -4.0769822105
H 6.8046988462 -0.8716685178 -3.1486884966
C 6.8791954102 -1.3316247077 -5.2494470948
H 6.6405796234 -2.3914251214 -5.1308511909
H 7.9656413801 -1.2356433461 -5.3200464011
H 6.4400741141 -0.9964195211 -6.1906382724
C 6.728784158 0.9698827233 -4.2180847044
H 7.8121658637 1.0777859548 -4.3125628797
H 6.4097688927 1.5480420604 -3.3489381946
H 6.2667966929 1.399380715 -5.1119952051
N 4.2113675054 -0.4188656278 -2.7516884996
H 3.1969710832 -0.5012959087 -2.8380056162
N 3.6409186275 -0.0967871821 -0.5651434873
N 5.9348294023 -0.02545796 -1.1923934565
O 4.1590953121 -0.8664885943 -4.9371753374
2- monomer open rotamer
C -0.063666586 -0.0843721802 -0.0270344034
C 0.0214486856 -0.2311963428 2.2181066284
H 0.6160296967 -0.3846880278 3.1159046998
C -1.3458240851 -0.001808015 2.293414162
H -1.872693549 0.0302149267 3.2378337664
C -1.9906594269 0.1898504594 1.0802751371
H -3.0603755713 0.3832983118 1.0396103298
C 0.2487446106 -0.1288729822 -2.5124088372
C 1.4601797654 -0.1760507394 -3.4881657394
H 2.184716248 0.5942524247 -3.2297814588
Cl 0.95584931 0.1177782589 -5.1406294028
Cl 2.3256228901 -1.7350210529 -3.3206554026
N 0.6842683112 -0.1377347292 -1.2026860929
H 1.6585011869 -0.3217178864 -1.0193245739
N 0.6792403494 -0.2773879328 1.0670756991
N -1.3645095753 0.1558708359 -0.0916320779
O -0.8803857664 -0.0560070582 -2.8890119291
2- monomer closedrotamer
C -0.0651297866 -0.0533607732 0.041372237
C 0.0562659991 -0.0770221601 2.2913745656
H 0.676396133 -0.1018620153 3.1844564643
C -1.3297520752 -0.0397614548 2.38390596
H -1.8441669805 -0.038032176 3.3352049664
C -2.0092816805 0.0036098836 1.1779168674
H -3.0951363787 0.0460174798 1.1457782018
C 0.356078712 -0.1364737173 -2.4916641982
C -1.1144129618 -0.382348254 -2.8573577263
H -1.7926945828 0.0795203816 -2.1509269103
Cl -1.4028346694 -2.1413782807 -2.7327194187
Cl -1.4707773123 0.2335853534 -4.4670270205
N 0.6638356649 -0.059501385 -1.1399790696
H 1.6605813629 -0.0167331661 -0.9834526456
N 0.7029881716 -0.0847634116 1.1345190456
N -1.392236956 0.0015740948 -0.0002948066
O 1.2264278612 -0.0494820621 -3.3118781731
2– open rotamer to closed rotamer transition state
C 1.6663819094 0.2149259504 0.3571735849
C 3.787035416 0.9450039041 0.216405511
H 4.4997179962 1.756053081 0.3508094935
C 4.1976468518 -0.2924114718 -0.2618991099
H 5.2292554532 -0.4987634344 -0.5139114476
C 3.1961080278 -1.2411963815 -0.4117436438
H 3.4178603981 -2.234745793 -0.7952089637
C -0.7174019172 -0.3024356534 0.1806846437
C -1.411789061 -1.1588476489 1.2520094019
H -1.7444194633 -0.4881927048 2.0440937772
Cl -0.2835736901 -2.2935114138 2.0174531865
Cl -2.8405397642 -1.9698891897 0.6148177607
N 0.3587551663 0.4787239142 0.7270253668
H 0.1655513003 1.4703781333 0.7473854052
N 2.5272167523 1.2203876526 0.5301775931
N 1.924989219 -1.0052410581 -0.1107268675
O -1.1027074146 -0.2029593063 -0.9373767022
2 dimer D1
C -0.20442 0.05018 0.04655
C -0.37458 0.70827 2.20974
H 0.12426 0.9522 3.14483
C -1.75224 0.7809 2.09084
H -2.3833 1.08094 2.9165
C -2.26794 0.44151 0.84682
H -3.33961 0.46351 0.66108
C 0.33143 -0.95874 -2.15081
C 1.54093 -0.97215 -3.11782
H 2.48759 -0.94458 -2.58487
Cl 1.48124 0.52287 -4.10044
Cl 1.5458 -2.41557 -4.11669
N 0.65499 -0.27597 -0.99355
H 1.6215 0.02478 -0.85533
N 0.41379 0.3282 1.20517
N -1.50956 0.08971 -0.18292
O -0.70899 -1.48367 -2.40671
C 4.20396 0.38507 0.53374
C 4.25026 1.2585 -1.55828
H 3.71184 1.50515 -2.47042
C 5.59967 1.53835 -1.4235
H 6.16844 2.01003 -2.21344
C 6.17258 1.17195 -0.21261
H 7.22853 1.34691 -0.01823
C 3.85201 -0.89336 2.62559
C 2.66685 -1.18957 3.57736
H 1.72448 -1.26515 3.04148
Cl 2.90041 -2.70113 4.43882
Cl 2.49255 0.19834 4.69418
N 3.41536 -0.16804 1.53312
H 2.41224 -0.01511 1.41433
N 3.54029 0.66678 -0.59861
N 5.488 0.61036 0.77491
O 4.96494 -1.26546 2.84103
2 dimer D2
C 2.35851 -0.37177 -1.0054
C 1.9663 -2.16881 -2.3129
H 1.28753 -2.96328 -2.61798
C 3.22068 -2.03694 -2.89287
H 3.57226 -2.70832 -3.66541
C 3.99551 -0.99153 -2.41055
H 4.99838 -0.81605 -2.79466
C 2.2874 1.70194 0.37868
C 1.30634 2.29243 1.4246
H 0.30971 1.86755 1.34667
N 1.83447 0.46679 -0.0318
H 0.93055 0.16076 0.31341
N 1.51745 -1.34984 -1.37145
N 3.58444 -0.15442 -1.46583
O 3.27335 2.27244 0.0197
Cl 1.90631 1.86823 3.05972
Cl 1.15306 4.03442 1.22347
C -1.10272 -1.94074 1.11988
C -0.84121 -3.59708 2.62067
H -1.119 -4.59251 2.95914
C 0.10366 -2.84404 3.30443
H 0.59593 -3.20966 4.1955
C 0.38538 -1.5975 2.76899
H 1.11945 -0.93847 3.22504
C -1.73638 -0.33879 -0.6824
C -2.57335 -0.28993 -1.97286
H -2.4565 0.70275 -2.39274
N -1.77887 -1.53661 -0.02895
H -2.37579 -2.26058 -0.39957
N -1.4542 -3.15989 1.52826
N -0.21047 -1.12944 1.6732
O -1.13365 0.64924 -0.35134
Cl -1.97566 -1.45047 -3.18033
Cl -4.30417 -0.52043 -1.63134
2 dimer D3
C 0.01037 -0.00873 -0.03302
C 0.00031 -0.08285 2.2226
H 0.56681 -0.08577 3.15099
C -1.38667 -0.15209 2.23475
H -1.95329 -0.20713 3.15439
C -1.99564 -0.15054 0.99082
H -3.07694 -0.20799 0.89337
C 0.53553 0.17742 -2.51231
C -0.91752 0.38866 -2.95332
H -1.61564 -0.09862 -2.28534
Cl -1.17708 -0.21808 -4.58359
Cl -1.25215 2.13877 -2.82311
N 0.80356 0.05954 -1.1721
H 1.81338 0.03169 -0.976
N 0.7118 -0.01008 1.10579
N -1.31143 -0.08322 -0.14678
O 1.43738 0.15141 -3.32026
C 4.76878 -0.03611 -1.61405
C 4.14649 0.01873 0.56875
H 3.33194 0.04683 1.28856
C 5.47681 0.00323 0.95842
H 5.77125 0.01968 1.99934
C 6.40426 -0.03664 -0.07377
H 7.47187 -0.05386 0.13569
C 5.0585 -0.07796 -4.09362
C 4.10345 -0.21021 -5.30686
H 3.11563 0.19621 -5.10892
Cl 4.7498 0.6347 -6.70999
Cl 3.85994 -1.95125 -5.62444
N 4.32137 -0.05441 -2.92308
H 3.30862 -0.04977 -3.00715
N 3.7767 -0.001 -0.70767
N 6.06992 -0.05672 -1.35762
O 6.24576 -0.024 -4.19986
2 dimer D4
C -0.20278 -0.15418 0.19849
C -0.20998 0.03707 2.44316
H 0.35403 0.20192 3.35847
C -1.5841 -0.17238 2.47639
H -2.14528 -0.17587 3.40118
C -2.186 -0.38211 1.24753
H -3.2554 -0.56325 1.16829
C 0.32038 -0.18886 -2.29264
C -1.14895 -0.16931 -2.73638
H -1.79922 -0.63342 -2.00629
Cl -1.35204 -0.99797 -4.27887
Cl -1.65239 1.54156 -2.82388
N 0.58771 -0.13696 -0.94686
H 1.58689 -0.04788 -0.74906
N 0.49118 0.04977 1.32002
N -1.50961 -0.37968 0.10238
O 1.21547 -0.21361 -3.10441
C 4.93471 -0.28088 -3.97744
C 4.94162 -0.46522 -6.2227
H 4.37213 -0.50389 -7.14857
C 6.32888 -0.55815 -6.23059
H 6.89493 -0.66686 -7.14598
C 6.93772 -0.50822 -4.98834
H 8.01815 -0.5809 -4.88783
C 4.39853 0.05377 -1.51145
C 5.85747 0.27323 -1.08774
H 6.55054 -0.24795 -1.73527
Cl 6.21105 2.01178 -1.28926
Cl 6.12004 -0.2671 0.56946
N 4.13744 -0.1418 -2.84519
H 3.13576 -0.1732 -3.04783
N 4.23388 -0.32658 -5.11224
N 6.25539 -0.37388 -3.85465
O 3.50306 0.08721 -0.70041
2 dimer D5
C -1.77979 1.37102 -0.25928
C -0.21034 3.01367 -0.28428
H 0.84696 3.26785 -0.2877
C -1.20706 3.98067 -0.30038
H -0.97988 5.03788 -0.31299
C -2.50796 3.50567 -0.30509
H -3.35395 4.18826 -0.32563
C -3.09257 -0.81903 -0.17517
C -4.46206 -0.15321 0.01264
H -4.49701 0.83853 -0.42023
Cl -4.70061 0.06855 1.76833
Cl -5.73835 -1.12886 -0.71169
N -1.98384 0.00168 -0.23823
H -1.11414 -0.54084 -0.26294
N -0.4846 1.71427 -0.2641
N -2.80961 2.20994 -0.28747
O -2.9644 -2.01492 -0.23228
C 1.77699 -1.36868 -0.26457
C 0.20753 -3.01123 -0.29495
H -0.84978 -3.2654 -0.29895
C 1.20424 -3.97817 -0.31473
H 0.97705 -5.03532 -0.33102
C 2.50514 -3.50315 -0.3181
H 3.35112 -4.18566 -0.34126
C 3.08976 0.82107 -0.17292
C 4.45934 0.1546 0.01194
H 4.49411 -0.8356 -0.42444
Cl 5.73531 1.13283 -0.70949
Cl 4.69866 -0.07333 1.76673
N 1.98103 0.00059 -0.23865
H 1.11131 0.54316 -0.2612
N 0.48179 -1.71191 -0.27026
N 2.80679 -2.2075 -0.29599
O 2.96157 2.01716 -0.22588
2 dimer D6
C -0.09638 -0.24255 0.14013
C -0.05646 -0.24285 2.39834
H 0.5281 -0.18465 3.31382
C -1.43658 -0.38706 2.44504
H -1.97941 -0.4433 3.37866
C -2.07027 -0.46011 1.21568
H -3.14857 -0.58034 1.14522
C 0.36569 -0.09359 -2.36
C -1.10511 0.05012 -2.77
H -1.76824 -0.44786 -2.07535
Cl -1.38171 -0.6032 -4.37878
Cl -1.5057 1.78894 -2.6703
N 0.66293 -0.16949 -1.01668
H 1.67566 -0.13931 -0.85445
N 0.62741 -0.16706 1.26456
N -1.41561 -0.39409 0.06127
O 1.25145 -0.10037 -3.17949
C 4.62583 0.03862 -1.59849
C 4.00266 0.23324 0.57797
H 3.18708 0.23121 1.2976
C 5.32307 0.41932 0.96076
H 5.60819 0.56901 1.99319
C 6.25039 0.40758 -0.06872
H 7.3096 0.55552 0.12912
C 4.86052 -0.35034 -4.10822
C 6.38801 -0.52356 -4.06612
H 6.84714 0.09113 -3.30277
Cl 6.72556 -2.21647 -3.59829
Cl 7.10655 -0.1185 -5.62171
N 4.20206 -0.15946 -2.89626
H 3.18793 -0.16844 -3.01604
N 3.64124 0.04181 -0.68566
N 5.91879 0.22515 -1.34094
O 4.23639 -0.41285 -5.12804
data_global
_publ_contact_author_name 'Borys Osmialowski'
_publ_contact_author_email ''
_publ_contact_author_address
;
University of Technology and Life Sciences,
Faculty of Technology and Chemical Engineering,
Seminaryjna 3,
PL-85-326 Bydgoszcz, Poland
;
loop_
_publ_author_name
_publ_author_address
'O\'smia\/lowski, Borys'
;
Department of Chemistry,
University of Technology and Life Sciences,
Seminaryjna 3, PL-85-326 Bydgoszcz
Poland
;
'Kolehmainen, Erkki'
;
Department of Chemistry
PO.BOX 35
40014 University of Jyv\"askyl\"a
Finland
;
'Valkonen, Arto'
;
Department of Chemistry
PO.BOX 35
40014 University of Jyv\"askyl\"a
Finland
;
'Kowalska, Magdalena'
;
Department of Chemistry,
University of Technology and Life Sciences,
Seminaryjna 3, PL-85-326 Bydgoszcz
Poland
;
'Ikonen, Satu'
;
Department of Chemistry
PO.BOX 35
40014 University of Jyv\"askyl\"a
Finland
;
_publ_requested_journal 'Journal of Physical Chemistry A'
data_1
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C8 H11 N3 O'
_chemical_formula_sum
'C8 H11 N3 O'
_chemical_formula_weight 165.20
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
'C' 'C' 0.0033 0.0016
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'H' 'H' 0.0000 0.0000
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'N' 'N' 0.0061 0.0033
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'O' 'O' 0.0106 0.0060
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting Monoclinic
_symmetry_space_group_name_H-M P21
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
_cell_length_a 9.2358(5)
_cell_length_b 10.2925(6)
_cell_length_c 9.3974(6)
_cell_angle_alpha 90.00
_cell_angle_beta 90.847(3)
_cell_angle_gamma 90.00
_cell_volume 893.21(9)
_cell_formula_units_Z 4
_cell_measurement_temperature 123(2)
_cell_measurement_reflns_used 1675
_cell_measurement_theta_min 0.407
_cell_measurement_theta_max 25.350
_exptl_crystal_description ?
_exptl_crystal_colour colourless
_exptl_crystal_size_max 0.20
_exptl_crystal_size_mid 0.10
_exptl_crystal_size_min 0.08
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.228
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 352
_exptl_absorpt_coefficient_mu 0.085
_exptl_absorpt_correction_type none
_exptl_absorpt_correction_T_min ?
_exptl_absorpt_correction_T_max ?
_exptl_absorpt_process_details ?
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 123(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Bruker Kappa APEX-II'
_diffrn_measurement_method '\f and \w scans'
_diffrn_detector_area_resol_mean 9
_diffrn_standards_number ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_diffrn_reflns_number 2920
_diffrn_reflns_av_R_equivalents 0.0000
_diffrn_reflns_av_sigmaI/netI 0.0325
_diffrn_reflns_limit_h_min -11
_diffrn_reflns_limit_h_max 11
_diffrn_reflns_limit_k_min -12
_diffrn_reflns_limit_k_max 12
_diffrn_reflns_limit_l_min -11
_diffrn_reflns_limit_l_max 11
_diffrn_reflns_theta_min 3.65
_diffrn_reflns_theta_max 25.24
_reflns_number_total 2920
_reflns_number_gt 2813
_reflns_threshold_expression >2\s(I)
_computing_data_collection 'Collect (Bruker, 2004)'
_computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_reduction 'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_structure_solution 'SIR-2002 (Burla, et al., 2003)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material
'SHELXL-97; MERCURY (Macrae, <i>et al.</i>, 2006)'
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0559P)^2^+0.7186P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_ls_hydrogen_treatment mixed
_refine_ls_extinction_method SHELXL
_refine_ls_extinction_coef 0.073(16)
_refine_ls_extinction_expression
'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^'
_refine_ls_number_reflns 2920
_refine_ls_number_parameters 229
_refine_ls_number_restraints 1
_refine_ls_R_factor_all 0.0542
_refine_ls_R_factor_gt 0.0510
_refine_ls_wR_factor_ref 0.1407
_refine_ls_wR_factor_gt 0.1369
_refine_ls_goodness_of_fit_ref 1.174
_refine_ls_restrained_S_all 1.174
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O9A O 0.7737(3) 0.0218(3) 0.1283(3) 0.0380(7) Uani 1 1 d . . .
N1A N 0.6680(4) 0.3704(3) -0.0818(3) 0.0281(7) Uani 1 1 d . . .
N3A N 0.6443(4) 0.2638(3) 0.1418(3) 0.0311(8) Uani 1 1 d . . .
N7A N 0.7272(3) 0.1545(3) -0.0616(3) 0.0231(7) Uani 1 1 d . . .
H7A H 0.741(5) 0.169(5) -0.150(5) 0.035 Uiso 1 1 d . . .
C2A C 0.6767(4) 0.2666(4) 0.0050(4) 0.0243(8) Uani 1 1 d . . .
C4A C 0.6005(5) 0.3773(4) 0.1967(4) 0.0344(9) Uani 1 1 d . . .
H4A H 0.5757 0.3796 0.2945 0.041 Uiso 1 1 calc R . .
C5A C 0.5894(4) 0.4899(4) 0.1199(4) 0.0307(9) Uani 1 1 d . . .
H5A H 0.5606 0.5697 0.1617 0.037 Uiso 1 1 calc R . .
C6A C 0.6230(4) 0.4799(4) -0.0222(4) 0.0317(9) Uani 1 1 d . . .
H6A H 0.6134 0.5551 -0.0803 0.038 Uiso 1 1 calc R . .
C8A C 0.7737(4) 0.0415(4) 0.0007(4) 0.0250(8) Uani 1 1 d . . .
C10A C 0.8373(4) -0.0546(4) -0.1033(4) 0.0293(9) Uani 1 1 d . . .
H10A H 0.7999 -0.0342 -0.2012 0.035 Uiso 1 1 calc R . .
C11A C 0.7917(6) -0.1929(4) -0.0639(6) 0.0465(12) Uani 1 1 d . . .
H11A H 0.8317 -0.2544 -0.1327 0.070 Uiso 1 1 calc R . .
H11B H 0.6858 -0.1991 -0.0656 0.070 Uiso 1 1 calc R . .
H11C H 0.8286 -0.2139 0.0317 0.070 Uiso 1 1 calc R . .
C12A C 1.0003(4) -0.0395(4) -0.1003(4) 0.0353(10) Uani 1 1 d . . .
H12A H 1.0261 0.0474 -0.1341 0.053 Uiso 1 1 calc R . .
H12B H 1.0437 -0.1051 -0.1621 0.053 Uiso 1 1 calc R . .
H12C H 1.0368 -0.0511 -0.0026 0.053 Uiso 1 1 calc R . .
O9B O 0.6186(3) 0.0436(3) 0.6169(3) 0.0346(7) Uani 1 1 d . . .
N1B N 0.9022(4) 0.3052(4) 0.4155(3) 0.0363(9) Uani 1 1 d . . .
N3B N 0.8479(3) 0.2170(3) 0.6432(3) 0.0276(7) Uani 1 1 d . . .
N7B N 0.7292(3) 0.1472(3) 0.4323(3) 0.0232(6) Uani 1 1 d . . .
H7B H 0.728(5) 0.155(5) 0.336(5) 0.035 Uiso 1 1 d . . .
C2B C 0.8306(4) 0.2251(4) 0.5020(4) 0.0230(8) Uani 1 1 d . . .
C4B C 0.9466(4) 0.2998(4) 0.6999(4) 0.0309(9) Uani 1 1 d . . .
H4B H 0.9621 0.2982 0.8001 0.037 Uiso 1 1 calc R . .
C5B C 1.0248(5) 0.3852(5) 0.6223(4) 0.0382(10) Uani 1 1 d . . .
H5B H 1.0940 0.4419 0.6650 0.046 Uiso 1 1 calc R . .
C6B C 0.9976(5) 0.3846(5) 0.4771(5) 0.0471(12) Uani 1 1 d . . .
H6B H 1.0494 0.4434 0.4189 0.056 Uiso 1 1 calc R . .
C8B C 0.6296(4) 0.0638(4) 0.4898(4) 0.0245(8) Uani 1 1 d . . .
C10B C 0.5293(4) -0.0002(4) 0.3801(4) 0.0271(8) Uani 1 1 d . . .
H10B H 0.5571 0.0297 0.2830 0.033 Uiso 1 1 calc R . .
C11B C 0.3715(4) 0.0380(4) 0.4057(4) 0.0328(9) Uani 1 1 d . . .
H11D H 0.3083 -0.0079 0.3378 0.049 Uiso 1 1 calc R . .
H11E H 0.3603 0.1319 0.3927 0.049 Uiso 1 1 calc R . .
H11F H 0.3451 0.0144 0.5029 0.049 Uiso 1 1 calc R . .
C12B C 0.5489(5) -0.1485(4) 0.3887(5) 0.0349(10) Uani 1 1 d . . .
H12D H 0.6491 -0.1710 0.3660 0.052 Uiso 1 1 calc R . .
H12E H 0.4829 -0.1907 0.3204 0.052 Uiso 1 1 calc R . .
H12F H 0.5273 -0.1783 0.4851 0.052 Uiso 1 1 calc R . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O9A 0.0469(16) 0.0419(18) 0.0253(14) 0.0079(12) 0.0037(11) 0.0172(15)
N1A 0.0350(17) 0.0251(18) 0.0240(16) 0.0008(13) -0.0017(13) 0.0031(14)
N3A 0.0416(18) 0.0290(18) 0.0229(15) 0.0008(13) 0.0092(13) 0.0064(16)
N7A 0.0286(15) 0.0228(15) 0.0179(14) -0.0002(13) 0.0022(12) -0.0007(13)
C2A 0.0242(18) 0.027(2) 0.0215(17) -0.0031(16) -0.0021(13) -0.0025(15)
C4A 0.041(2) 0.035(2) 0.027(2) -0.0035(17) 0.0035(17) 0.0065(19)
C5A 0.034(2) 0.027(2) 0.031(2) -0.0028(16) -0.0011(16) 0.0043(17)
C6A 0.036(2) 0.027(2) 0.032(2) 0.0042(17) -0.0024(16) 0.0012(17)
C8A 0.0233(17) 0.027(2) 0.0248(18) 0.0003(16) -0.0007(13) 0.0036(15)
C10A 0.0335(19) 0.030(2) 0.0243(19) -0.0012(15) -0.0017(15) 0.0059(17)
C11A 0.057(3) 0.028(2) 0.055(3) 0.001(2) -0.012(2) 0.003(2)
C12A 0.034(2) 0.040(3) 0.032(2) -0.0034(18) 0.0030(17) 0.0150(18)
O9B 0.0403(15) 0.0403(17) 0.0233(14) 0.0085(13) -0.0033(11) -0.0177(13)
N1B 0.0397(19) 0.043(2) 0.0262(16) 0.0029(15) -0.0008(14) -0.0180(16)
N3B 0.0305(16) 0.0292(17) 0.0231(16) 0.0007(13) -0.0009(12) -0.0063(14)
N7B 0.0257(15) 0.0241(15) 0.0197(15) 0.0023(13) -0.0002(12) -0.0028(13)
C2B 0.0202(17) 0.0242(19) 0.0246(17) -0.0026(15) 0.0030(13) -0.0006(15)
C4B 0.033(2) 0.036(2) 0.0236(18) -0.0008(17) -0.0015(14) -0.0004(18)
C5B 0.035(2) 0.049(3) 0.031(2) -0.0056(19) -0.0035(17) -0.013(2)
C6B 0.050(3) 0.056(3) 0.036(2) 0.004(2) 0.0006(19) -0.031(2)
C8B 0.0257(18) 0.0230(19) 0.0248(19) 0.0031(15) 0.0017(14) -0.0003(15)
C10B 0.0264(18) 0.030(2) 0.0251(18) 0.0038(15) -0.0004(14) -0.0084(16)
C11B 0.0309(19) 0.036(2) 0.032(2) 0.0003(17) -0.0038(15) -0.0043(17)
C12B 0.032(2) 0.031(2) 0.042(2) -0.0014(18) -0.0012(16) -0.0019(17)
_geom_special_details
;
All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell s.u.'s are taken
into account individually in the estimation of s.u.'s in distances, angles
and torsion angles; correlations between s.u.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O9A C8A 1.216(4) . ?
N1A C6A 1.329(5) . ?
N1A C2A 1.345(5) . ?
N3A C2A 1.325(4) . ?
N3A C4A 1.343(5) . ?
N7A C8A 1.368(5) . ?
N7A C2A 1.396(5) . ?
N7A H7A 0.86(5) . ?
C4A C5A 1.368(6) . ?
C4A H4A 0.9500 . ?
C5A C6A 1.379(5) . ?
C5A H5A 0.9500 . ?
C6A H6A 0.9500 . ?
C8A C10A 1.515(5) . ?
C10A C12A 1.514(6) . ?
C10A C11A 1.532(6) . ?
C10A H10A 1.0000 . ?
C11A H11A 0.9800 . ?
C11A H11B 0.9800 . ?
C11A H11C 0.9800 . ?
C12A H12A 0.9800 . ?
C12A H12B 0.9800 . ?
C12A H12C 0.9800 . ?
O9B C8B 1.218(4) . ?
N1B C6B 1.328(5) . ?
N1B C2B 1.339(5) . ?
N3B C2B 1.336(4) . ?
N3B C4B 1.352(5) . ?
N7B C8B 1.375(5) . ?
N7B C2B 1.390(5) . ?
N7B H7B 0.91(5) . ?
C4B C5B 1.357(6) . ?
C4B H4B 0.9500 . ?
C5B C6B 1.384(6) . ?
C5B H5B 0.9500 . ?
C6B H6B 0.9500 . ?
C8B C10B 1.525(5) . ?
C10B C11B 1.532(6) . ?
C10B C12B 1.539(6) . ?
C10B H10B 1.0000 . ?
C11B H11D 0.9800 . ?
C11B H11E 0.9800 . ?
C11B H11F 0.9800 . ?
C12B H12D 0.9800 . ?
C12B H12E 0.9800 . ?
C12B H12F 0.9800 . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6A N1A C2A 115.7(3) . . ?
C2A N3A C4A 115.3(3) . . ?
C8A N7A C2A 128.0(3) . . ?
C8A N7A H7A 121(3) . . ?
C2A N7A H7A 110(3) . . ?
N3A C2A N1A 126.4(3) . . ?
N3A C2A N7A 119.9(3) . . ?
N1A C2A N7A 113.7(3) . . ?
N3A C4A C5A 123.7(4) . . ?
N3A C4A H4A 118.2 . . ?
C5A C4A H4A 118.2 . . ?
C4A C5A C6A 115.6(4) . . ?
C4A C5A H5A 122.2 . . ?
C6A C5A H5A 122.2 . . ?
N1A C6A C5A 123.2(4) . . ?
N1A C6A H6A 118.4 . . ?
C5A C6A H6A 118.4 . . ?
O9A C8A N7A 124.0(3) . . ?
O9A C8A C10A 122.2(3) . . ?
N7A C8A C10A 113.6(3) . . ?
C12A C10A C8A 108.4(3) . . ?
C12A C10A C11A 111.5(4) . . ?
C8A C10A C11A 109.9(3) . . ?
C12A C10A H10A 109.0 . . ?
C8A C10A H10A 109.0 . . ?
C11A C10A H10A 109.0 . . ?
C10A C11A H11A 109.5 . . ?
C10A C11A H11B 109.5 . . ?
H11A C11A H11B 109.5 . . ?
C10A C11A H11C 109.5 . . ?
H11A C11A H11C 109.5 . . ?
H11B C11A H11C 109.5 . . ?
C10A C12A H12A 109.5 . . ?
C10A C12A H12B 109.5 . . ?
H12A C12A H12B 109.5 . . ?
C10A C12A H12C 109.5 . . ?
H12A C12A H12C 109.5 . . ?
H12B C12A H12C 109.5 . . ?
C6B N1B C2B 116.4(3) . . ?
C2B N3B C4B 115.0(3) . . ?
C8B N7B C2B 128.7(3) . . ?
C8B N7B H7B 117(3) . . ?
C2B N7B H7B 114(3) . . ?
N3B C2B N1B 126.0(3) . . ?
N3B C2B N7B 120.1(3) . . ?
N1B C2B N7B 113.8(3) . . ?
N3B C4B C5B 123.9(4) . . ?
N3B C4B H4B 118.1 . . ?
C5B C4B H4B 118.1 . . ?
C4B C5B C6B 115.9(4) . . ?
C4B C5B H5B 122.1 . . ?
C6B C5B H5B 122.1 . . ?
N1B C6B C5B 122.8(4) . . ?
N1B C6B H6B 118.6 . . ?
C5B C6B H6B 118.6 . . ?
O9B C8B N7B 124.0(3) . . ?
O9B C8B C10B 122.0(3) . . ?
N7B C8B C10B 114.0(3) . . ?
C8B C10B C11B 110.6(3) . . ?
C8B C10B C12B 108.9(3) . . ?
C11B C10B C12B 111.0(3) . . ?
C8B C10B H10B 108.8 . . ?
C11B C10B H10B 108.8 . . ?
C12B C10B H10B 108.8 . . ?
C10B C11B H11D 109.5 . . ?
C10B C11B H11E 109.5 . . ?
H11D C11B H11E 109.5 . . ?
C10B C11B H11F 109.5 . . ?
H11D C11B H11F 109.5 . . ?
H11E C11B H11F 109.5 . . ?
C10B C12B H12D 109.5 . . ?
C10B C12B H12E 109.5 . . ?
H12D C12B H12E 109.5 . . ?
C10B C12B H12F 109.5 . . ?
H12D C12B H12F 109.5 . . ?
H12E C12B H12F 109.5 . . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4A N3A C2A N1A -0.9(6) . . . . ?
C4A N3A C2A N7A 178.3(3) . . . . ?
C6A N1A C2A N3A 0.4(6) . . . . ?
C6A N1A C2A N7A -178.8(3) . . . . ?
C8A N7A C2A N3A -12.6(6) . . . . ?
C8A N7A C2A N1A 166.7(3) . . . . ?
C2A N3A C4A C5A -0.2(6) . . . . ?
N3A C4A C5A C6A 1.7(6) . . . . ?
C2A N1A C6A C5A 1.3(6) . . . . ?
C4A C5A C6A N1A -2.2(6) . . . . ?
C2A N7A C8A O9A 2.0(6) . . . . ?
C2A N7A C8A C10A -173.3(3) . . . . ?
O9A C8A C10A C12A -78.8(5) . . . . ?
N7A C8A C10A C12A 96.6(4) . . . . ?
O9A C8A C10A C11A 43.4(5) . . . . ?
N7A C8A C10A C11A -141.2(3) . . . . ?
C4B N3B C2B N1B 0.7(6) . . . . ?
C4B N3B C2B N7B -178.2(3) . . . . ?
C6B N1B C2B N3B -0.8(6) . . . . ?
C6B N1B C2B N7B 178.1(4) . . . . ?
C8B N7B C2B N3B 5.4(6) . . . . ?
C8B N7B C2B N1B -173.7(4) . . . . ?
C2B N3B C4B C5B -0.5(6) . . . . ?
N3B C4B C5B C6B 0.5(7) . . . . ?
C2B N1B C6B C5B 0.8(8) . . . . ?
C4B C5B C6B N1B -0.6(8) . . . . ?
C2B N7B C8B O9B -1.9(6) . . . . ?
C2B N7B C8B C10B 176.7(3) . . . . ?
O9B C8B C10B C11B 60.5(5) . . . . ?
N7B C8B C10B C11B -118.0(4) . . . . ?
O9B C8B C10B C12B -61.7(5) . . . . ?
N7B C8B C10B C12B 119.8(4) . . . . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N7A H7A N3B 0.86(5) 2.25(5) 3.073(4) 162(4) 1_554
N7B H7B N3A 0.91(5) 2.26(5) 3.073(5) 148(4) .
N7B H7B O9A 0.91(5) 2.43(5) 3.167(4) 139(4) .
_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full 25.24
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max 0.233
_refine_diff_density_min -0.228
_refine_diff_density_rms 0.052
data_2
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C6 H5 Cl2 N3 O'
_chemical_formula_sum
'C6 H5 Cl2 N3 O'
_chemical_formula_weight 206.03
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
'C' 'C' 0.0033 0.0016
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'H' 'H' 0.0000 0.0000
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'N' 'N' 0.0061 0.0033
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'O' 'O' 0.0106 0.0060
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'Cl' 'Cl' 0.1484 0.1585
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting Tetragonal
_symmetry_space_group_name_H-M P41212
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, -z+3/4'
'-x+1/2, y+1/2, -z+1/4'
'-y, -x, -z+1/2'
'y, x, -z'
'y+1/2, -x+1/2, z+3/4'
'-y+1/2, x+1/2, z+1/4'
_cell_length_a 9.7577(2)
_cell_length_b 9.7577(2)
_cell_length_c 18.0008(5)
_cell_angle_alpha 90.00
_cell_angle_beta 90.00
_cell_angle_gamma 90.00
_cell_volume 1713.90(7)
_cell_formula_units_Z 8
_cell_measurement_temperature 123(2)
_cell_measurement_reflns_used 1624
_cell_measurement_theta_min 0.407
_cell_measurement_theta_max 25.350
_exptl_crystal_description block
_exptl_crystal_colour colourless
_exptl_crystal_size_max 0.18
_exptl_crystal_size_mid 0.16
_exptl_crystal_size_min 0.12
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.597
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 832
_exptl_absorpt_coefficient_mu 0.709
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_correction_T_min 0.8830
_exptl_absorpt_correction_T_max 0.9197
_exptl_absorpt_process_details sadabs
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 123(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Bruker Kappa APEX-II'
_diffrn_measurement_method '\f and \w scans'
_diffrn_detector_area_resol_mean 9
_diffrn_standards_number ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_diffrn_reflns_number 13822
_diffrn_reflns_av_R_equivalents 0.0412
_diffrn_reflns_av_sigmaI/netI 0.0350
_diffrn_reflns_limit_h_min -12
_diffrn_reflns_limit_h_max 12
_diffrn_reflns_limit_k_min -13
_diffrn_reflns_limit_k_max 11
_diffrn_reflns_limit_l_min -20
_diffrn_reflns_limit_l_max 23
_diffrn_reflns_theta_min 3.16
_diffrn_reflns_theta_max 28.29
_reflns_number_total 2099
_reflns_number_gt 1818
_reflns_threshold_expression >2\s(I)
_computing_data_collection 'Collect (Bruker, 2004)'
_computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_reduction 'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_structure_solution 'SIR-2002 (Burla, et al., 2003)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material
'SHELXL-97; MERCURY (Macrae, <i>et al.</i>, 2006)'
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0133P)^2^+1.4470P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_ls_hydrogen_treatment mixed
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_abs_structure_details
'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack 0.09(9)
_refine_ls_number_reflns 2099
_refine_ls_number_parameters 112
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0529
_refine_ls_R_factor_gt 0.0428
_refine_ls_wR_factor_ref 0.0859
_refine_ls_wR_factor_gt 0.0822
_refine_ls_goodness_of_fit_ref 1.068
_refine_ls_restrained_S_all 1.068
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.82686(7) 0.02266(11) 0.83690(4) 0.0658(3) Uani 1 1 d . . .
Cl2 Cl 0.67433(11) 0.27735(8) 0.84773(5) 0.0709(3) Uani 1 1 d . . .
O9 O 0.58959(19) 0.0271(2) 0.94511(9) 0.0417(5) Uani 1 1 d . . .
N1 N 0.2399(2) -0.1057(2) 0.82620(10) 0.0307(5) Uani 1 1 d . . .
N3 N 0.3257(2) -0.0810(2) 0.94986(10) 0.0303(4) Uani 1 1 d . . .
N7 N 0.44813(19) -0.00556(19) 0.84497(9) 0.0241(4) Uani 1 1 d . . .
H7 H 0.442(3) 0.006(3) 0.7946(15) 0.036 Uiso 1 1 d . . .
C2 C 0.3323(2) -0.0675(2) 0.87654(11) 0.0235(4) Uani 1 1 d . . .
C4 C 0.2085(3) -0.1373(3) 0.97476(13) 0.0342(6) Uani 1 1 d . . .
H4 H 0.1976 -0.1496 1.0268 0.041 Uiso 1 1 calc R . .
C5 C 0.1039(3) -0.1779(3) 0.92874(13) 0.0346(6) Uani 1 1 d . . .
H5 H 0.0209 -0.2150 0.9477 0.042 Uiso 1 1 calc R . .
C6 C 0.1258(3) -0.1618(3) 0.85311(14) 0.0360(6) Uani 1 1 d . . .
H6 H 0.0571 -0.1917 0.8194 0.043 Uiso 1 1 calc R . .
C8 C 0.5641(2) 0.0354(2) 0.87954(11) 0.0251(5) Uani 1 1 d . . .
C10 C 0.6657(3) 0.1014(3) 0.82615(13) 0.0357(6) Uani 1 1 d . . .
H10 H 0.6331 0.0894 0.7739 0.043 Uiso 1 1 calc R . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl1 0.0320(3) 0.1207(8) 0.0446(4) -0.0075(5) 0.0036(3) 0.0006(4)
Cl2 0.1059(7) 0.0441(4) 0.0628(5) 0.0213(4) -0.0365(5) -0.0369(5)
O9 0.0404(10) 0.0685(14) 0.0164(8) 0.0051(8) -0.0060(7) -0.0161(9)
N1 0.0335(11) 0.0386(12) 0.0199(9) -0.0026(8) -0.0004(8) -0.0077(9)
N3 0.0405(12) 0.0333(11) 0.0170(9) 0.0029(8) 0.0001(9) -0.0049(10)
N7 0.0294(9) 0.0292(9) 0.0137(8) 0.0015(7) -0.0001(7) -0.0034(8)
C2 0.0308(11) 0.0223(10) 0.0175(10) -0.0006(8) 0.0003(9) 0.0003(9)
C4 0.0448(15) 0.0381(14) 0.0196(11) 0.0055(10) 0.0041(10) -0.0065(11)
C5 0.0397(14) 0.0331(13) 0.0310(12) 0.0002(10) 0.0054(10) -0.0103(11)
C6 0.0384(14) 0.0412(14) 0.0284(12) -0.0041(11) 0.0009(11) -0.0107(11)
C8 0.0297(11) 0.0278(11) 0.0179(10) 0.0018(8) -0.0009(8) -0.0012(9)
C10 0.0367(13) 0.0499(16) 0.0204(11) 0.0037(10) -0.0046(10) -0.0155(11)
_geom_special_details
;
All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell s.u.'s are taken
into account individually in the estimation of s.u.'s in distances, angles
and torsion angles; correlations between s.u.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C10 1.761(3) . ?
Cl2 C10 1.762(3) . ?
O9 C8 1.209(3) . ?
N1 C6 1.331(3) . ?
N1 C2 1.332(3) . ?
N3 C2 1.328(3) . ?
N3 C4 1.345(3) . ?
N7 C8 1.352(3) . ?
N7 C2 1.402(3) . ?
N7 H7 0.92(3) . ?
C4 C5 1.373(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.387(3) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C8 C10 1.524(3) . ?
C10 H10 1.0000 . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 N1 C2 115.7(2) . . ?
C2 N3 C4 114.4(2) . . ?
C8 N7 C2 128.00(18) . . ?
C8 N7 H7 118.2(17) . . ?
C2 N7 H7 113.8(17) . . ?
N3 C2 N1 128.0(2) . . ?
N3 C2 N7 119.0(2) . . ?
N1 C2 N7 113.01(18) . . ?
N3 C4 C5 123.3(2) . . ?
N3 C4 H4 118.4 . . ?
C5 C4 H4 118.4 . . ?
C4 C5 C6 116.4(2) . . ?
C4 C5 H5 121.8 . . ?
C6 C5 H5 121.8 . . ?
N1 C6 C5 122.2(2) . . ?
N1 C6 H6 118.9 . . ?
C5 C6 H6 118.9 . . ?
O9 C8 N7 127.0(2) . . ?
O9 C8 C10 120.7(2) . . ?
N7 C8 C10 112.29(18) . . ?
C8 C10 Cl1 109.11(17) . . ?
C8 C10 Cl2 107.68(18) . . ?
Cl1 C10 Cl2 111.00(14) . . ?
C8 C10 H10 109.7 . . ?
Cl1 C10 H10 109.7 . . ?
Cl2 C10 H10 109.7 . . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 N3 C2 N1 -1.9(4) . . . . ?
C4 N3 C2 N7 177.8(2) . . . . ?
C6 N1 C2 N3 1.5(4) . . . . ?
C6 N1 C2 N7 -178.2(2) . . . . ?
C8 N7 C2 N3 5.5(4) . . . . ?
C8 N7 C2 N1 -174.7(2) . . . . ?
C2 N3 C4 C5 0.1(4) . . . . ?
N3 C4 C5 C6 1.8(4) . . . . ?
C2 N1 C6 C5 0.7(4) . . . . ?
C4 C5 C6 N1 -2.2(4) . . . . ?
C2 N7 C8 O9 -0.5(4) . . . . ?
C2 N7 C8 C10 -178.8(2) . . . . ?
O9 C8 C10 Cl1 53.1(3) . . . . ?
N7 C8 C10 Cl1 -128.53(17) . . . . ?
O9 C8 C10 Cl2 -67.4(3) . . . . ?
N7 C8 C10 Cl2 110.91(19) . . . . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N7 H7 O9 0.92(3) 2.18(3) 2.923(2) 137(2) 7_554
N7 H7 N3 0.92(3) 2.38(3) 3.160(3) 143(2) 7_554
_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_theta_full 28.29
_diffrn_measured_fraction_theta_full 0.985
_refine_diff_density_max 0.289
_refine_diff_density_min -0.458
_refine_diff_density_rms 0.051
References
1. Ośmiałowski B, Kolehmainen E, Dobosz R, Gawinecki R, Kauppinen R, Valkonen A, Koivukorpi J and Rissanen K (2010) J. Phys. Chem. A 114:10421
2. COLLECT, W.I. Bruker AXS, Inc., Madison, Wisconsin (USA), 2004
3. Otwinowski Z and Minor W (1997) In: JCW Carter and RM Sweet (ed) Processing of X-ray diffraction data collected in oscillation mode,
4. SADABS, W. I. Bruker AXS Inc., Madison, WIsconsin (USA), 2004
5. Burla MC, Camalli M, Carrozzini B, Cascarano GL, Giacovazzo C, Polidori G and Spagna R (2003) J. Appl. Crystallogr. 36:1103
6. Sheldrick GM (2008) Acta Crystallog. A 64:112
7. Farrugia LJ (1997) J. Appl. Crystallogr. 30:565
8. Macrae CF, Edgington PR, McCabe P, Pidcock E, Shields GP, Taylor R, Towler M and van de Streek J (2006) J. Appl. Crystallogr. 39:453
1