3D, 2D and 1D networks via N-H···O and N-H···N hydrogen bonding by the bis-amide analogues: Effect of chain lengths and odd-even spacers
GARGI MUKHERJEE and KUMAR BIRADHA*
Department of Chemistry, Indian Institute of Technology, Kharagpur 721302, India
E-mail:
Supporting Information
1HNMR Spectra of 1a, 2c, 2d and 3d
Spectroscopic analysis:
1H-NMR for:
Compound 1a:
Compound 2c:
Compound 2d:
Compound 3d:
data_1a
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety ?
_chemical_formula_sum
'C13 H12 N4 O2'
_chemical_formula_weight 256.27
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 orthorhombic
_symmetry_space_group_name_H-M Fdd2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'x+1/4, -y+1/4, z+1/4'
'-x+1/4, y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'x+1/4, -y+3/4, z+3/4'
'-x+1/4, y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'x+3/4, -y+1/4, z+3/4'
'-x+3/4, y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'x+3/4, -y+3/4, z+1/4'
'-x+3/4, y+3/4, z+1/4'
_cell_length_a 20.679(7)
_cell_length_b 28.501(10)
_cell_length_c 4.1182(15)
_cell_angle_alpha 90.00
_cell_angle_beta 90.00
_cell_angle_gamma 90.00
_cell_volume 2427.1(15)
_cell_formula_units_Z 8
_cell_measurement_temperature 293(2)
_cell_measurement_reflns_used 1140
_cell_measurement_theta_min 2.43
_cell_measurement_theta_max 26.00
_exptl_crystal_description block
_exptl_crystal_colour colorless
_exptl_crystal_size_max 0.16
_exptl_crystal_size_mid 0.13
_exptl_crystal_size_min 0.09
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.403
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 1072
_exptl_absorpt_coefficient_mu 0.099
_exptl_absorpt_correction_type ?
_exptl_absorpt_correction_T_min ?
_exptl_absorpt_correction_T_max ?
_exptl_absorpt_process_details ?
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 293(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 ?
_diffrn_measurement_method ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_diffrn_reflns_number 5624
_diffrn_reflns_av_R_equivalents 0.0479
_diffrn_reflns_av_sigmaI/netI 0.0397
_diffrn_reflns_limit_h_min -23
_diffrn_reflns_limit_h_max 24
_diffrn_reflns_limit_k_min -34
_diffrn_reflns_limit_k_max 34
_diffrn_reflns_limit_l_min -4
_diffrn_reflns_limit_l_max 5
_diffrn_reflns_theta_min 2.43
_diffrn_reflns_theta_max 26.00
_reflns_number_total 1140
_reflns_number_gt 916
_reflns_threshold_expression >2sigma(I)
_computing_data_collection ?
_computing_cell_refinement ?
_computing_data_reduction ?
_computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics ?
_computing_publication_material ?
_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^ > 2sigma(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^)+(0.1000P)^2^+0.0000P] 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 2(3)
_refine_ls_number_reflns 1140
_refine_ls_number_parameters 87
_refine_ls_number_restraints 1
_refine_ls_R_factor_all 0.0563
_refine_ls_R_factor_gt 0.0387
_refine_ls_wR_factor_ref 0.1246
_refine_ls_wR_factor_gt 0.1128
_refine_ls_goodness_of_fit_ref 0.864
_refine_ls_restrained_S_all 0.864
_refine_ls_shift/su_max 0.008
_refine_ls_shift/su_mean 0.001
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
N11 N -0.00232(8) 0.04271(6) 0.3254(5) 0.0357(5) Uani 1 1 d . . .
H11 H 0.0324 0.0588 0.3532 0.043 Uiso 1 1 calc R . .
C11 C 0.0000 0.0000 0.1394(8) 0.0368(8) Uani 1 2 d S . .
H11A H 0.0378 0.0011 0.0000 0.044 Uiso 0.50 1 calc P . .
H11B H -0.0378 -0.0011 0.0000 0.044 Uiso 0.50 1 calc P . .
O21 O -0.10714(8) 0.03387(6) 0.4518(5) 0.0560(6) Uani 1 1 d . . .
N21 N -0.12481(9) 0.16061(7) 0.9062(6) 0.0485(6) Uani 1 1 d . . .
C21 C -0.05888(9) 0.10549(7) 0.6108(6) 0.0337(5) Uani 1 1 d . . .
C22 C -0.11465(10) 0.11822(8) 0.7739(7) 0.0404(6) Uani 1 1 d . . .
H22 H -0.1473 0.0959 0.7931 0.048 Uiso 1 1 calc R . .
C23 C -0.07727(11) 0.19181(8) 0.8757(8) 0.0507(7) Uani 1 1 d . . .
H23 H -0.0835 0.2217 0.9606 0.061 Uiso 1 1 calc R . .
C24 C -0.01928(12) 0.18208(8) 0.7249(8) 0.0527(8) Uani 1 1 d . . .
H24 H 0.0131 0.2047 0.7140 0.063 Uiso 1 1 calc R . .
C25 C -0.01005(11) 0.13842(8) 0.5907(7) 0.0436(6) Uani 1 1 d . . .
H25 H 0.0287 0.1311 0.4875 0.052 Uiso 1 1 calc R . .
C26 C -0.05805(10) 0.05779(8) 0.4562(6) 0.0355(5) Uani 1 1 d . . .
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
N11 0.0281(9) 0.0320(9) 0.0469(12) -0.0019(8) 0.0019(8) 0.0016(7)
C11 0.0373(17) 0.0353(16) 0.038(2) 0.000 0.000 0.0051(13)
O21 0.0340(9) 0.0505(10) 0.0834(15) -0.0209(10) 0.0092(9) -0.0105(7)
N21 0.0331(11) 0.0470(11) 0.0653(15) -0.0107(11) 0.0099(11) 0.0049(9)
C21 0.0264(11) 0.0324(11) 0.0423(13) 0.0017(10) 0.0002(10) 0.0029(8)
C22 0.0266(11) 0.0417(12) 0.0529(16) -0.0041(11) 0.0019(11) -0.0017(10)
C23 0.0413(13) 0.0382(12) 0.0727(19) -0.0143(13) 0.0005(14) 0.0036(10)
C24 0.0392(14) 0.0391(13) 0.080(2) -0.0076(14) 0.0123(14) -0.0059(10)
C25 0.0291(11) 0.0416(13) 0.0601(17) -0.0040(13) 0.0116(12) 0.0010(9)
C26 0.0290(12) 0.0347(11) 0.0427(13) 0.0021(10) 0.0000(10) 0.0018(9)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds 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
N11 C26 1.343(3) . ?
N11 C11 1.439(3) . ?
C11 N11 1.439(3) 2 ?
O21 C26 1.223(3) . ?
N21 C23 1.332(3) . ?
N21 C22 1.342(3) . ?
C21 C25 1.381(3) . ?
C21 C22 1.383(3) . ?
C21 C26 1.501(3) . ?
C23 C24 1.379(4) . ?
C24 C25 1.375(3) . ?
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
C26 N11 C11 120.85(16) . . ?
N11 C11 N11 115.7(3) . 2 ?
C23 N21 C22 116.6(2) . . ?
C25 C21 C22 117.4(2) . . ?
C25 C21 C26 125.57(19) . . ?
C22 C21 C26 116.93(18) . . ?
N21 C22 C21 124.3(2) . . ?
N21 C23 C24 123.4(2) . . ?
C23 C24 C25 118.9(2) . . ?
C21 C25 C24 119.3(2) . . ?
O21 C26 N11 121.9(2) . . ?
O21 C26 C21 120.1(2) . . ?
N11 C26 C21 118.01(18) . . ?
_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full 26.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max 0.125
_refine_diff_density_min -0.162
_refine_diff_density_rms 0.036
data_2c
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety ?
_chemical_formula_sum
'C17 H24 N4 O4'
_chemical_formula_weight 348.40
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 C2/c
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
_cell_length_a 17.7550(12)
_cell_length_b 9.1736(7)
_cell_length_c 14.2042(16)
_cell_angle_alpha 90.00
_cell_angle_beta 126.398(3)
_cell_angle_gamma 90.00
_cell_volume 1862.2(3)
_cell_formula_units_Z 4
_cell_measurement_temperature 296(2)
_cell_measurement_reflns_used 1719
_cell_measurement_theta_min 2.64
_cell_measurement_theta_max 25.49
_exptl_crystal_description rod
_exptl_crystal_colour colorless
_exptl_crystal_size_max 0.25
_exptl_crystal_size_mid 0.12
_exptl_crystal_size_min 0.09
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.243
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 744
_exptl_absorpt_coefficient_mu 0.090
_exptl_absorpt_correction_type ?
_exptl_absorpt_correction_T_min ?
_exptl_absorpt_correction_T_max ?
_exptl_absorpt_process_details ?
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 296(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 ?
_diffrn_measurement_method ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_diffrn_reflns_number 9949
_diffrn_reflns_av_R_equivalents 0.0463
_diffrn_reflns_av_sigmaI/netI 0.0322
_diffrn_reflns_limit_h_min -21
_diffrn_reflns_limit_h_max 21
_diffrn_reflns_limit_k_min -11
_diffrn_reflns_limit_k_max 10
_diffrn_reflns_limit_l_min -15
_diffrn_reflns_limit_l_max 17
_diffrn_reflns_theta_min 2.64
_diffrn_reflns_theta_max 25.49
_reflns_number_total 1719
_reflns_number_gt 1281
_reflns_threshold_expression >2sigma(I)
_computing_data_collection ?
_computing_cell_refinement ?
_computing_data_reduction ?
_computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics ?
_computing_publication_material ?
_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^ > 2sigma(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^)+(0.1000P)^2^+0.0000P] 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_number_reflns 1719
_refine_ls_number_parameters 123
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0622
_refine_ls_R_factor_gt 0.0426
_refine_ls_wR_factor_ref 0.1547
_refine_ls_wR_factor_gt 0.1370
_refine_ls_goodness_of_fit_ref 1.107
_refine_ls_restrained_S_all 1.107
_refine_ls_shift/su_max 0.001
_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
N11 N 0.55388(11) 0.7698(2) 0.07153(14) 0.0564(5) Uani 1 1 d . . .
O11 O 0.33182(10) 0.46342(18) 0.09425(12) 0.0676(5) Uani 1 1 d . . .
C12 C 0.38968(12) 0.7223(2) -0.04003(15) 0.0484(5) Uani 1 1 d . . .
H12 H 0.3292 0.7482 -0.1024 0.058 Uiso 1 1 calc R . .
C13 C 0.40537(11) 0.60359(19) 0.02954(14) 0.0390(4) Uani 1 1 d . . .
C16 C 0.32691(12) 0.51169(19) 0.00973(15) 0.0430(4) Uani 1 1 d . . .
C14 C 0.49662(12) 0.5706(2) 0.12070(15) 0.0452(5) Uani 1 1 d . . .
H14 H 0.5099 0.4921 0.1698 0.054 Uiso 1 1 calc R . .
C15 C 0.56780(12) 0.6557(2) 0.13786(16) 0.0529(5) Uani 1 1 d . . .
H15 H 0.6290 0.6320 0.1993 0.063 Uiso 1 1 calc R . .
C11 C 0.46571(14) 0.8013(2) -0.01473(16) 0.0543(5) Uani 1 1 d . . .
H11 H 0.4544 0.8819 -0.0611 0.065 Uiso 1 1 calc R . .
N21 N 0.25714(10) 0.48547(17) -0.10082(13) 0.0478(4) Uani 1 1 d . . .
H21 H 0.2601 0.5232 -0.1540 0.057 Uiso 1 1 calc R . .
C21 C 0.17543(11) 0.3968(2) -0.13864(16) 0.0502(5) Uani 1 1 d . . .
H21A H 0.1865 0.3460 -0.0715 0.060 Uiso 1 1 calc . . .
H21B H 0.1667 0.3240 -0.1939 0.060 Uiso 1 1 calc . . .
C22 C 0.08786(12) 0.4863(2) -0.19489(17) 0.0499(5) Uani 1 1 d . . .
H22A H 0.0819 0.5476 -0.2546 0.060 Uiso 1 1 calc . . .
H22B H 0.0935 0.5496 -0.1363 0.060 Uiso 1 1 calc . . .
C23 C 0.0000 0.3950(3) -0.2500 0.0455(6) Uani 1 2 d S . .
H23A H -0.0056(13) 0.330(2) -0.3098(15) 0.055 Uiso 1 1 d . . .
O1W O 0.22389(11) 0.43488(19) 0.18025(13) 0.0636(5) Uani 1 1 d . . .
H1O H 0.2514(15) 0.438(2) 0.1506(18) 0.050 Uiso 1 1 d . . .
H2O H 0.1753(15) 0.381(2) 0.1393(17) 0.050 Uiso 1 1 d . . .
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
N11 0.0497(9) 0.0664(11) 0.0568(10) -0.0100(8) 0.0336(8) -0.0165(8)
O11 0.0586(9) 0.0961(12) 0.0477(8) 0.0043(7) 0.0313(7) -0.0255(8)
C12 0.0420(9) 0.0542(11) 0.0405(10) 0.0025(8) 0.0198(8) -0.0034(8)
C13 0.0371(9) 0.0482(10) 0.0359(9) -0.0035(7) 0.0240(8) -0.0051(7)
C16 0.0373(9) 0.0529(10) 0.0405(10) 0.0016(7) 0.0240(8) -0.0042(7)
C14 0.0411(9) 0.0514(10) 0.0412(10) 0.0023(7) 0.0234(8) 0.0003(8)
C15 0.0374(9) 0.0670(12) 0.0505(11) -0.0089(9) 0.0240(9) -0.0065(8)
C11 0.0629(12) 0.0511(11) 0.0521(11) 0.0012(8) 0.0359(10) -0.0131(9)
N21 0.0328(8) 0.0637(10) 0.0413(9) 0.0035(7) 0.0190(7) -0.0074(7)
C21 0.0331(9) 0.0536(11) 0.0524(11) 0.0005(8) 0.0192(8) -0.0052(7)
C22 0.0364(10) 0.0534(11) 0.0570(12) -0.0018(8) 0.0261(9) -0.0013(8)
C23 0.0355(12) 0.0520(15) 0.0482(15) 0.000 0.0244(12) 0.000
O1W 0.0496(9) 0.0924(12) 0.0562(9) -0.0204(8) 0.0354(8) -0.0231(8)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds 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
N11 C11 1.326(3) . ?
N11 C15 1.329(3) . ?
O11 C16 1.233(2) . ?
C12 C11 1.379(3) . ?
C12 C13 1.383(2) . ?
C13 C14 1.380(2) . ?
C13 C16 1.505(2) . ?
C16 N21 1.323(2) . ?
C14 C15 1.379(3) . ?
N21 C21 1.460(2) . ?
C21 C22 1.502(3) . ?
C22 C23 1.516(2) . ?
C23 C22 1.516(2) 2_554 ?
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
C11 N11 C15 116.59(15) . . ?
C11 C12 C13 118.48(16) . . ?
C14 C13 C12 118.03(15) . . ?
C14 C13 C16 119.58(15) . . ?
C12 C13 C16 122.39(15) . . ?
O11 C16 N21 124.46(16) . . ?
O11 C16 C13 119.75(15) . . ?
N21 C16 C13 115.77(14) . . ?
C13 C14 C15 118.95(17) . . ?
N11 C15 C14 123.73(17) . . ?
N11 C11 C12 124.21(17) . . ?
C16 N21 C21 124.36(15) . . ?
N21 C21 C22 112.35(15) . . ?
C21 C22 C23 113.35(16) . . ?
C22 C23 C22 113.0(2) . 2_554 ?
_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full 25.49
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max 0.217
_refine_diff_density_min -0.183
_refine_diff_density_rms 0.038
data_2d
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety ?
_chemical_formula_sum
'C19 H24 N4 O2'
_chemical_formula_weight 340.42
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 P2(1)/c
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
_cell_length_a 4.8639(5)
_cell_length_b 18.3835(19)
_cell_length_c 20.485(2)
_cell_angle_alpha 90.00
_cell_angle_beta 96.746(4)
_cell_angle_gamma 90.00
_cell_volume 1819.0(3)
_cell_formula_units_Z 4
_cell_measurement_temperature 293(2)
_cell_measurement_reflns_used 3225
_cell_measurement_theta_min 1.49
_cell_measurement_theta_max 25.50
_exptl_crystal_description block
_exptl_crystal_colour colorless
_exptl_crystal_size_max 0.14
_exptl_crystal_size_mid 0.12
_exptl_crystal_size_min 0.10
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.243
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 728
_exptl_absorpt_coefficient_mu 0.083
_exptl_absorpt_correction_type ?
_exptl_absorpt_correction_T_min ?
_exptl_absorpt_correction_T_max ?
_exptl_absorpt_process_details ?
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 293(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 ?
_diffrn_measurement_method ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_diffrn_reflns_number 21158
_diffrn_reflns_av_R_equivalents 0.1449
_diffrn_reflns_av_sigmaI/netI 0.1060
_diffrn_reflns_limit_h_min -5
_diffrn_reflns_limit_h_max 5
_diffrn_reflns_limit_k_min -22
_diffrn_reflns_limit_k_max 21
_diffrn_reflns_limit_l_min -24
_diffrn_reflns_limit_l_max 24
_diffrn_reflns_theta_min 1.49
_diffrn_reflns_theta_max 25.50
_reflns_number_total 3225
_reflns_number_gt 1078
_reflns_threshold_expression >2sigma(I)
_computing_data_collection ?
_computing_cell_refinement ?
_computing_data_reduction ?
_computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics ?
_computing_publication_material ?
_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^ > 2sigma(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^)+(0.1000P)^2^+0.0000P] 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 0.010(3)
_refine_ls_extinction_expression
'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^'
_refine_ls_number_reflns 3225
_refine_ls_number_parameters 227
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.2397
_refine_ls_R_factor_gt 0.0744
_refine_ls_wR_factor_ref 0.2178
_refine_ls_wR_factor_gt 0.1586
_refine_ls_goodness_of_fit_ref 0.871
_refine_ls_restrained_S_all 0.871
_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
O11 O 0.4405(9) 0.34125(18) 0.31333(17) 0.1191(15) Uani 1 1 d . . .
N11 N 1.2320(10) 0.4180(3) 0.4773(2) 0.1117(16) Uani 1 1 d . . .
C11 C 1.1887(14) 0.4703(3) 0.4308(4) 0.0989(18) Uani 1 1 d . . .
H11 H 1.3041 0.5109 0.4339 0.119 Uiso 1 1 calc R . .
C12 C 0.9834(15) 0.4663(3) 0.3795(3) 0.0918(17) Uani 1 1 d . . .
H12 H 0.9655 0.5034 0.3483 0.110 Uiso 1 1 calc R . .
C13 C 0.8028(13) 0.4087(3) 0.3728(3) 0.0827(16) Uani 1 1 d . . .
C14 C 0.8435(16) 0.3550(3) 0.4201(3) 0.107(2) Uani 1 1 d . . .
H14 H 0.7292 0.3143 0.4177 0.128 Uiso 1 1 calc R . .
C15 C 1.0498(18) 0.3619(4) 0.4696(4) 0.112(2) Uani 1 1 d . . .
H15 H 1.0691 0.3252 0.5010 0.135 Uiso 1 1 calc R . .
C16 C 0.5724(14) 0.3991(3) 0.3184(3) 0.0873(17) Uani 1 1 d . . .
N21 N 0.8367(10) 0.2704(3) -0.3898(3) 0.1073(15) Uani 1 1 d . . .
O21 O 0.2424(8) 0.41187(17) -0.25130(17) 0.1170(14) Uani 1 1 d . . .
C21 C 0.6462(13) 0.3227(3) -0.4030(3) 0.1109(19) Uani 1 1 d . . .
H21 H 0.6177 0.3416 -0.4454 0.133 Uiso 1 1 calc R . .
C22 C 0.4882(12) 0.3501(3) -0.3555(3) 0.1034(18) Uani 1 1 d . . .
H22 H 0.3601 0.3870 -0.3663 0.124 Uiso 1 1 calc R . .
C23 C 0.5237(10) 0.3221(2) -0.2934(2) 0.0793(14) Uani 1 1 d . . .
C24 C 0.7227(11) 0.2688(3) -0.2805(3) 0.0933(16) Uani 1 1 d . . .
H24 H 0.7550 0.2484 -0.2388 0.112 Uiso 1 1 calc R . .
C25 C 0.8720(11) 0.2458(2) -0.3291(3) 0.0985(18) Uani 1 1 d . . .
H25 H 1.0070 0.2105 -0.3186 0.118 Uiso 1 1 calc R . .
C26 C 0.3516(10) 0.3516(3) -0.2438(2) 0.0841(16) Uani 1 1 d . . .
N31 N 0.5150(10) 0.4541(2) 0.2770(2) 0.0910(14) Uani 1 1 d . . .
H31 H 0.6006 0.4947 0.2847 0.109 Uiso 1 1 calc R . .
N32 N 0.3258(8) 0.30921(18) -0.19166(18) 0.0870(13) Uani 1 1 d . . .
H32 H 0.4004 0.2667 -0.1901 0.104 Uiso 1 1 calc R . .
C31 C 0.3133(13) 0.4480(3) 0.2195(3) 0.1061(19) Uani 1 1 d . . .
H31A H 0.2141 0.4937 0.2125 0.127 Uiso 1 1 calc . . .
H31B H 0.1802 0.4105 0.2267 0.127 Uiso 1 1 calc . . .
C32 C 0.4474(11) 0.4300(3) 0.1600(2) 0.0974(17) Uani 1 1 d . . .
H32A H 0.5541 0.3857 0.1686 0.117 Uiso 1 1 calc . . .
H32B H 0.5761 0.4686 0.1527 0.117 Uiso 1 1 calc . . .
C33 C 0.2519(11) 0.4196(2) 0.0980(3) 0.0988(17) Uani 1 1 d . . .
H33A H 0.1155 0.3833 0.1062 0.119 Uiso 1 1 calc . . .
H33B H 0.1543 0.4649 0.0877 0.119 Uiso 1 1 calc . . .
C34 C 0.3891(12) 0.3963(3) 0.0387(3) 0.1133(19) Uani 1 1 d . . .
H34A H 0.5112 0.4352 0.0282 0.136 Uiso 1 1 calc . . .
H34B H 0.5039 0.3543 0.0511 0.136 Uiso 1 1 calc . . .
C35 C 0.2017(11) 0.3776(3) -0.0227(3) 0.0958(17) Uani 1 1 d . . .
H35A H 0.0791 0.3384 -0.0130 0.115 Uiso 1 1 calc . . .
H35B H 0.0882 0.4195 -0.0363 0.115 Uiso 1 1 calc . . .
C36 C 0.3577(12) 0.3547(3) -0.0786(3) 0.1007(17) Uani 1 1 d . . .
H36A H 0.4719 0.3949 -0.0901 0.121 Uiso 1 1 calc . . .
H36B H 0.4798 0.3146 -0.0641 0.121 Uiso 1 1 calc . . .
C37 C 0.1761(12) 0.3322(3) -0.1372(3) 0.1001(18) Uani 1 1 d . . .
H37A H 0.0607 0.2923 -0.1256 0.120 Uiso 1 1 calc . . .
H37B H 0.0550 0.3724 -0.1518 0.120 Uiso 1 1 calc . . .
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
O11 0.182(4) 0.068(2) 0.122(3) -0.023(2) 0.078(3) -0.024(2)
N11 0.120(4) 0.112(4) 0.114(4) 0.005(3) 0.058(3) 0.019(4)
C11 0.110(5) 0.084(4) 0.112(5) -0.013(4) 0.050(4) -0.009(4)
C12 0.127(5) 0.069(4) 0.089(4) -0.006(3) 0.056(4) 0.015(4)
C13 0.111(5) 0.054(3) 0.094(4) -0.004(3) 0.063(4) 0.005(3)
C14 0.157(7) 0.083(4) 0.092(5) -0.006(4) 0.067(5) -0.001(4)
C15 0.145(7) 0.095(5) 0.112(6) 0.017(4) 0.076(5) 0.013(5)
C16 0.117(5) 0.065(4) 0.092(4) -0.023(3) 0.061(4) -0.016(4)
N21 0.120(4) 0.091(3) 0.122(4) -0.001(3) 0.059(3) 0.009(3)
O21 0.162(3) 0.059(2) 0.148(3) 0.020(2) 0.090(3) 0.020(2)
C21 0.118(5) 0.121(5) 0.104(5) 0.017(4) 0.054(4) 0.001(4)
C22 0.129(5) 0.088(4) 0.104(4) 0.007(3) 0.059(4) 0.006(3)
C23 0.100(4) 0.058(3) 0.089(4) 0.006(3) 0.046(3) -0.010(3)
C24 0.110(4) 0.070(3) 0.110(4) 0.011(3) 0.056(4) 0.002(3)
C25 0.109(4) 0.076(3) 0.122(5) 0.013(3) 0.062(4) -0.001(3)
C26 0.106(4) 0.054(3) 0.101(4) -0.001(3) 0.051(3) -0.007(3)
N31 0.133(4) 0.068(3) 0.080(3) -0.003(2) 0.048(3) -0.004(3)
N32 0.117(3) 0.061(2) 0.092(3) 0.004(2) 0.050(3) 0.004(2)
C31 0.130(5) 0.093(4) 0.106(5) -0.016(3) 0.058(4) -0.005(3)
C32 0.120(4) 0.116(4) 0.061(3) 0.019(3) 0.028(3) 0.046(3)
C33 0.134(5) 0.086(3) 0.086(4) 0.010(3) 0.053(4) 0.012(3)
C34 0.127(5) 0.139(5) 0.081(4) 0.033(4) 0.043(4) 0.051(4)
C35 0.112(5) 0.099(4) 0.082(4) 0.011(3) 0.036(4) 0.026(3)
C36 0.119(5) 0.112(4) 0.078(4) 0.013(3) 0.041(4) 0.029(3)
C37 0.133(5) 0.082(3) 0.098(4) -0.011(3) 0.069(4) -0.015(3)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds 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
O11 C16 1.240(5) . ?
N11 C15 1.357(7) . ?
N11 C11 1.353(6) . ?
C11 C12 1.364(7) . ?
C11 H11 0.9300 . ?
C12 C13 1.373(7) . ?
C12 H12 0.9300 . ?
C13 C14 1.381(7) . ?
C13 C16 1.495(7) . ?
C14 C15 1.346(8) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 N31 1.328(6) . ?
N21 C25 1.315(6) . ?
N21 C21 1.341(6) . ?
O21 C26 1.231(5) . ?
C21 C22 1.402(6) . ?
C21 H21 0.9300 . ?
C22 C23 1.365(6) . ?
C22 H22 0.9300 . ?
C23 C24 1.382(6) . ?
C23 C26 1.491(6) . ?
C24 C25 1.366(6) . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?
C26 N32 1.340(5) . ?
N31 C31 1.446(6) . ?
N31 H31 0.8600 . ?
N32 C37 1.464(5) . ?
N32 H32 0.8600 . ?
C31 C32 1.485(6) . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C32 C33 1.507(6) . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C33 C34 1.515(6) . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C34 C35 1.504(7) . ?
C34 H34A 0.9700 . ?
C34 H34B 0.9700 . ?
C35 C36 1.506(6) . ?
C35 H35A 0.9700 . ?
C35 H35B 0.9700 . ?
C36 C37 1.464(7) . ?
C36 H36A 0.9700 . ?
C36 H36B 0.9700 . ?
C37 H37A 0.9700 . ?
C37 H37B 0.9700 . ?
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
C15 N11 C11 114.4(6) . . ?
C12 C11 N11 122.9(6) . . ?
C12 C11 H11 118.5 . . ?
N11 C11 H11 118.5 . . ?
C11 C12 C13 121.3(6) . . ?
C11 C12 H12 119.3 . . ?
C13 C12 H12 119.3 . . ?
C12 C13 C14 116.4(6) . . ?
C12 C13 C16 125.4(6) . . ?
C14 C13 C16 118.1(6) . . ?
C15 C14 C13 119.5(7) . . ?
C15 C14 H14 120.2 . . ?
C13 C14 H14 120.2 . . ?
C14 C15 N11 125.4(7) . . ?
C14 C15 H15 117.3 . . ?
N11 C15 H15 117.3 . . ?
O11 C16 N31 122.1(7) . . ?
O11 C16 C13 119.9(6) . . ?
N31 C16 C13 118.0(5) . . ?
C25 N21 C21 116.6(5) . . ?
N21 C21 C22 122.7(5) . . ?
N21 C21 H21 118.7 . . ?
C22 C21 H21 118.7 . . ?
C21 C22 C23 119.5(5) . . ?
C21 C22 H22 120.3 . . ?
C23 C22 H22 120.3 . . ?
C22 C23 C24 117.0(4) . . ?
C22 C23 C26 118.6(5) . . ?
C24 C23 C26 124.4(5) . . ?
C25 C24 C23 120.1(5) . . ?
C25 C24 H24 120.0 . . ?
C23 C24 H24 120.0 . . ?
N21 C25 C24 124.1(5) . . ?
N21 C25 H25 117.9 . . ?
C24 C25 H25 117.9 . . ?
O21 C26 N32 122.9(4) . . ?
O21 C26 C23 120.7(4) . . ?
N32 C26 C23 116.4(4) . . ?
C16 N31 C31 122.2(5) . . ?
C16 N31 H31 118.9 . . ?
C31 N31 H31 118.9 . . ?
C26 N32 C37 122.8(4) . . ?
C26 N32 H32 118.6 . . ?
C37 N32 H32 118.6 . . ?
N31 C31 C32 111.4(5) . . ?
N31 C31 H31A 109.4 . . ?
C32 C31 H31A 109.4 . . ?
N31 C31 H31B 109.4 . . ?
C32 C31 H31B 109.4 . . ?
H31A C31 H31B 108.0 . . ?
C31 C32 C33 115.2(5) . . ?
C31 C32 H32A 108.5 . . ?
C33 C32 H32A 108.5 . . ?
C31 C32 H32B 108.5 . . ?
C33 C32 H32B 108.5 . . ?
H32A C32 H32B 107.5 . . ?
C34 C33 C32 114.7(5) . . ?
C34 C33 H33A 108.6 . . ?
C32 C33 H33A 108.6 . . ?
C34 C33 H33B 108.6 . . ?
C32 C33 H33B 108.6 . . ?
H33A C33 H33B 107.6 . . ?
C35 C34 C33 117.1(5) . . ?
C35 C34 H34A 108.0 . . ?
C33 C34 H34A 108.0 . . ?
C35 C34 H34B 108.0 . . ?
C33 C34 H34B 108.0 . . ?
H34A C34 H34B 107.3 . . ?
C36 C35 C34 113.0(5) . . ?
C36 C35 H35A 109.0 . . ?
C34 C35 H35A 109.0 . . ?
C36 C35 H35B 109.0 . . ?
C34 C35 H35B 109.0 . . ?
H35A C35 H35B 107.8 . . ?
C37 C36 C35 113.1(5) . . ?
C37 C36 H36A 109.0 . . ?
C35 C36 H36A 109.0 . . ?
C37 C36 H36B 109.0 . . ?
C35 C36 H36B 109.0 . . ?
H36A C36 H36B 107.8 . . ?
N32 C37 C36 113.6(5) . . ?
N32 C37 H37A 108.9 . . ?
C36 C37 H37A 108.9 . . ?
N32 C37 H37B 108.9 . . ?
C36 C37 H37B 108.9 . . ?
H37A C37 H37B 107.7 . . ?
_diffrn_measured_fraction_theta_max 0.955
_diffrn_reflns_theta_full 25.50
_diffrn_measured_fraction_theta_full 0.955
_refine_diff_density_max 0.124
_refine_diff_density_min -0.125
_refine_diff_density_rms 0.033
data_3d
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety ?
_chemical_formula_sum
'C38 H48 N8 O4'
_chemical_formula_weight 680.84
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 Triclinic
_symmetry_space_group_name_H-M P-1
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
_cell_length_a 4.715(4)
_cell_length_b 10.493(8)
_cell_length_c 19.088(14)
_cell_angle_alpha 102.52(3)
_cell_angle_beta 93.32(3)
_cell_angle_gamma 95.97(3)
_cell_volume 913.6(12)
_cell_formula_units_Z 1
_cell_measurement_temperature 293(2)
_cell_measurement_reflns_used 3148
_cell_measurement_theta_min 2.00
_cell_measurement_theta_max 24.99
_exptl_crystal_description block
_exptl_crystal_colour colorless
_exptl_crystal_size_max 0.23
_exptl_crystal_size_mid 0.12
_exptl_crystal_size_min 0.08
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.237
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 364
_exptl_absorpt_coefficient_mu 0.082
_exptl_absorpt_correction_type ?
_exptl_absorpt_correction_T_min ?
_exptl_absorpt_correction_T_max ?
_exptl_absorpt_process_details ?
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 293(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 ?
_diffrn_measurement_method ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_diffrn_reflns_number 10367
_diffrn_reflns_av_R_equivalents 0.1431
_diffrn_reflns_av_sigmaI/netI 0.1562
_diffrn_reflns_limit_h_min -5
_diffrn_reflns_limit_h_max 5
_diffrn_reflns_limit_k_min -12
_diffrn_reflns_limit_k_max 11
_diffrn_reflns_limit_l_min -22
_diffrn_reflns_limit_l_max 22
_diffrn_reflns_theta_min 2.00
_diffrn_reflns_theta_max 24.99
_reflns_number_total 3148
_reflns_number_gt 1047
_reflns_threshold_expression >2sigma(I)
_computing_data_collection ?
_computing_cell_refinement ?
_computing_data_reduction ?
_computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics ?
_computing_publication_material ?
_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^ > 2sigma(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^)+(0.1394P)^2^+0.0000P] 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 0.011(6)
_refine_ls_extinction_expression
'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^'
_refine_ls_number_reflns 3148
_refine_ls_number_parameters 227
_refine_ls_number_restraints 1
_refine_ls_R_factor_all 0.2400
_refine_ls_R_factor_gt 0.0773
_refine_ls_wR_factor_ref 0.2351
_refine_ls_wR_factor_gt 0.1743
_refine_ls_goodness_of_fit_ref 0.722
_refine_ls_restrained_S_all 0.788
_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
N11 N 0.3261(16) 0.6231(7) 0.0661(4) 0.145(3) Uani 1 1 d . . .
N12 N 0.8941(9) 0.8547(4) 0.1837(2) 0.0613(12) Uani 1 1 d D . .
H12 H 0.9776 0.9301 0.1809 0.074 Uiso 1 1 calc R . .
C11 C 0.6736(13) 0.7996(5) 0.1287(3) 0.0611(15) Uani 1 1 d . . .
C12 C 0.5428(15) 0.6722(6) 0.1181(3) 0.093(2) Uani 1 1 d . . .
H12A H 0.6048 0.6185 0.1473 0.112 Uiso 1 1 calc R . .
C13 C 0.254(2) 0.7070(13) 0.0215(4) 0.151(5) Uani 1 1 d . . .
H13 H 0.1112 0.6762 -0.0158 0.181 Uiso 1 1 calc R . .
C14 C 0.3837(19) 0.8299(9) 0.0309(4) 0.111(3) Uani 1 1 d . . .
H14 H 0.3289 0.8839 0.0010 0.133 Uiso 1 1 calc R . .
C15 C 0.5865(15) 0.8731(6) 0.0820(3) 0.088(2) Uani 1 1 d . . .
H15 H 0.6774 0.9580 0.0872 0.106 Uiso 1 1 calc R . .
N21 N 0.9259(12) 1.8615(4) 0.8177(3) 0.0818(15) Uani 1 1 d . . .
N22 N 1.1683(9) 1.5542(4) 0.7191(2) 0.0618(12) Uani 1 1 d . . .
H22 H 1.1483 1.4746 0.7244 0.074 Uiso 1 1 calc R . .
C21 C 1.0299(11) 1.6436(5) 0.7670(2) 0.0555(14) Uani 1 1 d . . .
C22 C 1.0541(13) 1.7781(5) 0.7707(3) 0.0762(17) Uani 1 1 d . . .
H22A H 1.1656 1.8114 0.7386 0.091 Uiso 1 1 calc R . .
C23 C 0.7701(13) 1.8143(6) 0.8636(3) 0.0751(17) Uani 1 1 d . . .
H23 H 0.6807 1.8722 0.8967 0.090 Uiso 1 1 calc R . .
C24 C 0.7344(13) 1.6834(6) 0.8643(3) 0.0775(18) Uani 1 1 d . . .
H24 H 0.6236 1.6534 0.8975 0.093 Uiso 1 1 calc R . .
C25 C 0.8643(12) 1.5971(5) 0.8154(3) 0.0681(16) Uani 1 1 d . . .
H25 H 0.8409 1.5078 0.8149 0.082 Uiso 1 1 calc R . .
O31 O 0.9048(10) 0.7006(4) 0.24512(19) 0.0922(14) Uani 1 1 d D . .
O32 O 1.3656(11) 1.6826(4) 0.6499(2) 0.1152(18) Uani 1 1 d . . .
C31 C 0.9924(13) 0.8099(5) 0.2383(3) 0.0651(16) Uani 1 1 d . . .
C32 C 1.2151(12) 0.8989(5) 0.2902(3) 0.0712(16) Uani 1 1 d . . .
H32A H 1.3212 0.9579 0.2657 0.085 Uiso 1 1 calc . . .
H32B H 1.3486 0.8470 0.3084 0.085 Uiso 1 1 calc . . .
C33 C 1.0780(12) 0.9789(5) 0.3529(3) 0.0681(15) Uani 1 1 d . . .
H33A H 0.9472 1.0313 0.3341 0.082 Uiso 1 1 calc . . .
H33B H 0.9664 0.9189 0.3758 0.082 Uiso 1 1 calc . . .
C34 C 1.2884(12) 1.0688(5) 0.4089(3) 0.0657(15) Uani 1 1 d . . .
H34A H 1.4275 1.1147 0.3847 0.079 Uiso 1 1 calc . . .
H34B H 1.3905 1.0158 0.4352 0.079 Uiso 1 1 calc . . .
C35 C 1.1546(12) 1.1699(5) 0.4625(3) 0.0719(16) Uani 1 1 d . . .
H35A H 1.0159 1.1241 0.4868 0.086 Uiso 1 1 calc . . .
H35B H 1.0525 1.2230 0.4363 0.086 Uiso 1 1 calc . . .
C36 C 1.3696(11) 1.2604(5) 0.5188(3) 0.0645(15) Uani 1 1 d . . .
H36A H 1.4552 1.2087 0.5489 0.077 Uiso 1 1 calc . . .
H36B H 1.5211 1.2984 0.4946 0.077 Uiso 1 1 calc . . .
C37 C 1.2373(12) 1.3708(5) 0.5664(3) 0.0720(16) Uani 1 1 d . . .
H37A H 1.0816 1.3329 0.5893 0.086 Uiso 1 1 calc . . .
H37B H 1.1575 1.4243 0.5364 0.086 Uiso 1 1 calc . . .
C38 C 1.4499(13) 1.4577(6) 0.6238(3) 0.0757(17) Uani 1 1 d . . .
H38A H 1.5119 1.4064 0.6572 0.091 Uiso 1 1 calc . . .
H38B H 1.6166 1.4867 0.6013 0.091 Uiso 1 1 calc . . .
C39 C 1.3297(13) 1.5766(6) 0.6652(3) 0.0687(16) Uani 1 1 d . . .
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
N11 0.121(6) 0.164(7) 0.121(5) -0.008(5) -0.016(5) -0.018(5)
N12 0.077(3) 0.049(3) 0.062(3) 0.022(2) 0.015(2) 0.004(2)
C11 0.079(4) 0.055(4) 0.054(3) 0.015(3) 0.020(3) 0.016(3)
C12 0.118(6) 0.068(4) 0.090(4) 0.023(3) -0.010(4) -0.006(4)
C13 0.092(7) 0.278(15) 0.062(5) -0.019(8) -0.003(5) 0.054(9)
C14 0.114(8) 0.159(8) 0.072(5) 0.042(5) -0.003(5) 0.050(6)
C15 0.103(6) 0.087(5) 0.081(4) 0.030(4) 0.005(4) 0.015(4)
N21 0.117(4) 0.054(3) 0.077(3) 0.014(3) 0.028(3) 0.016(3)
N22 0.081(3) 0.050(3) 0.062(3) 0.024(2) 0.021(2) 0.009(2)
C21 0.068(4) 0.044(3) 0.058(3) 0.021(3) 0.002(3) 0.006(3)
C22 0.104(5) 0.058(4) 0.075(4) 0.029(3) 0.023(4) 0.007(4)
C23 0.091(5) 0.073(5) 0.066(4) 0.018(3) 0.017(3) 0.018(4)
C24 0.089(5) 0.071(4) 0.081(4) 0.026(3) 0.031(4) 0.019(4)
C25 0.089(4) 0.050(3) 0.074(3) 0.031(3) 0.019(3) 0.003(3)
O31 0.138(4) 0.059(2) 0.086(3) 0.041(2) -0.005(3) -0.003(3)
O32 0.173(5) 0.077(3) 0.117(3) 0.049(3) 0.078(3) 0.017(3)
C31 0.087(5) 0.059(4) 0.059(3) 0.026(3) 0.020(3) 0.015(3)
C32 0.082(4) 0.075(4) 0.060(3) 0.016(3) 0.009(3) 0.021(3)
C33 0.070(4) 0.066(4) 0.068(3) 0.017(3) 0.009(3) 0.008(3)
C34 0.070(4) 0.068(4) 0.062(3) 0.018(3) 0.004(3) 0.012(3)
C35 0.075(4) 0.072(4) 0.069(3) 0.013(3) 0.012(3) 0.012(3)
C36 0.065(4) 0.070(4) 0.060(3) 0.016(3) 0.007(3) 0.010(3)
C37 0.072(4) 0.075(4) 0.072(3) 0.020(3) 0.005(3) 0.014(3)
C38 0.080(4) 0.075(4) 0.071(4) 0.015(3) 0.015(3) 0.007(4)
C39 0.081(4) 0.068(4) 0.062(3) 0.028(3) 0.015(3) -0.001(3)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds 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
N11 C12 1.358(8) . ?
N11 C13 1.404(12) . ?
N12 C31 1.312(6) . ?
N12 C11 1.415(6) . ?
C11 C12 1.380(7) . ?
C11 C15 1.372(7) . ?
C13 C14 1.339(12) . ?
C14 C15 1.296(8) . ?
N21 C22 1.331(6) . ?
N21 C23 1.318(7) . ?
N22 C39 1.360(6) . ?
N22 C21 1.403(6) . ?
C21 C25 1.378(6) . ?
C21 C22 1.389(7) . ?
C23 C24 1.370(7) . ?
C24 C25 1.371(7) . ?
O31 C31 1.214(6) . ?
O32 C39 1.208(6) . ?
C31 C32 1.494(7) . ?
C32 C33 1.523(7) . ?
C33 C34 1.504(7) . ?
C34 C35 1.521(7) . ?
C35 C36 1.522(7) . ?
C36 C37 1.522(7) . ?
C37 C38 1.512(7) . ?
C38 C39 1.508(7) . ?
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
C12 N11 C13 116.1(8) . . ?
C31 N12 C11 130.7(5) . . ?
C12 C11 N12 123.1(5) . . ?
C12 C11 C15 117.2(6) . . ?
N12 C11 C15 119.7(5) . . ?
C11 C12 N11 121.8(6) . . ?
N11 C13 C14 122.2(9) . . ?
C15 C14 C13 119.4(9) . . ?
C14 C15 C11 123.2(7) . . ?
C22 N21 C23 118.3(5) . . ?
C39 N22 C21 128.7(4) . . ?
N22 C21 C25 118.6(5) . . ?
N22 C21 C22 124.4(5) . . ?
C25 C21 C22 117.0(5) . . ?
N21 C22 C21 123.3(5) . . ?
N21 C23 C24 122.6(5) . . ?
C23 C24 C25 119.1(6) . . ?
C24 C25 C21 119.6(5) . . ?
O31 C31 N12 120.6(5) . . ?
O31 C31 C32 122.5(5) . . ?
N12 C31 C32 116.9(5) . . ?
C31 C32 C33 110.7(5) . . ?
C34 C33 C32 114.2(5) . . ?
C33 C34 C35 114.4(5) . . ?
C34 C35 C36 113.9(5) . . ?
C37 C36 C35 113.2(5) . . ?
C36 C37 C38 112.9(5) . . ?
C39 C38 C37 113.2(5) . . ?
O32 C39 N22 122.6(5) . . ?
O32 C39 C38 122.4(5) . . ?
N22 C39 C38 115.0(5) . . ?
_diffrn_measured_fraction_theta_max 0.975
_diffrn_reflns_theta_full 24.99
_diffrn_measured_fraction_theta_full 0.975
_refine_diff_density_max 0.176
_refine_diff_density_min -0.164
_refine_diff_density_rms 0.043