Supplementary Material (ESI) for Chemical Communications This journal is © The Royal Society of Chemistry 2001 data_global _journal_coden_Cambridge 182 _publ_requested_journal 'Chemical Communications' loop_ _publ_author_name 'Adams, Harry' 'Bernad Jr, Pablo L.' 'Eggleston, Drake S.' 'Haltiwanger, R. Curtis' 'Harris, Kenneth D. M.' 'Harris, Guy A.' 'Hunter, Christopher A.' 'Kariuki, Benson M.' 'Livingstone, David J.' 'McCabe, James F.' _publ_contact_author_name 'Prof Christopher A Hunter' _publ_contact_author_address ; Prof Christopher A Hunter Department of Chemistry Centre for Chemical Biology, Krebs Institute for Biomolecular Science, Universit Sheffield S3 7HF UNITED KINGDOM ; _publ_contact_author_email 'C.Hunter@Sheffield.ac.uk' data_gah01 _database_code_CSD 158573 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common 'N-phenyl 4 t-butylbenzamide' _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C17 H19 N O' _chemical_formula_weight 253.33 _chemical_melting_point ? _chemical_compound_source ? 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' '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' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' '-x, -y, -z' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' 'x-1/2, y, -z-1/2' _cell_length_a 12.6531(11) _cell_length_b 9.2906(15) _cell_length_c 25.595(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3008.9(6) _cell_formula_units_Z 8 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.118 _exptl_crystal_density_method ? _exptl_crystal_F_000 1088 _exptl_absorpt_coefficient_mu 0.069 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Rigaku R-Axis' _diffrn_measurement_method 'Image plate scans' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9461 _diffrn_reflns_av_R_equivalents 0.1440 _diffrn_reflns_av_sigmaI/netI 0.1830 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 1.59 _diffrn_reflns_theta_max 24.41 _reflns_number_total 2298 _reflns_number_observed 1016 _reflns_observed_criterion >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0283P)^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 ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2298 _refine_ls_number_parameters 175 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2241 _refine_ls_R_factor_obs 0.0613 _refine_ls_wR_factor_all 0.1605 _refine_ls_wR_factor_obs 0.1133 _refine_ls_goodness_of_fit_all 0.941 _refine_ls_goodness_of_fit_obs 1.041 _refine_ls_restrained_S_all 0.941 _refine_ls_restrained_S_obs 1.041 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group O1 O 0.1699(2) 0.0447(3) 0.64003(11) 0.0650(10) Uani 1 d . . N1 N 0.2647(3) 0.2443(3) 0.65880(13) 0.0530(10) Uani 1 d . . H1 H 0.2752(3) 0.3316(3) 0.64895(13) 0.064 Uiso 1 calc R . C1 C 0.0966(4) 0.3775(5) 0.4188(2) 0.0638(13) Uani 1 d . . C2 C 0.1515(6) 0.5159(7) 0.4044(2) 0.180(4) Uani 1 d . . H2A H 0.1237(30) 0.5510(31) 0.3719(11) 0.216 Uiso 1 calc R . H2B H 0.2260(8) 0.4986(13) 0.4008(20) 0.216 Uiso 1 calc R . H2C H 0.1399(34) 0.5861(18) 0.4313(10) 0.216 Uiso 1 calc R . C3 C 0.1212(6) 0.2672(7) 0.3791(2) 0.189(4) Uani 1 d . . H3A H 0.1003(39) 0.3013(24) 0.3453(3) 0.227 Uiso 1 calc R . H3B H 0.0835(31) 0.1802(20) 0.3871(12) 0.227 Uiso 1 calc R . H3C H 0.1958(8) 0.2482(40) 0.3792(14) 0.227 Uiso 1 calc R . C4 C -0.0209(5) 0.4110(6) 0.4149(2) 0.119(2) Uani 1 d . . H4A H -0.0357(6) 0.4535(34) 0.3815(6) 0.143 Uiso 1 calc R . H4B H -0.0404(7) 0.4768(29) 0.4421(8) 0.143 Uiso 1 calc R . H4C H -0.0607(5) 0.3236(8) 0.4185(14) 0.143 Uiso 1 calc R . C5 C 0.1243(3) 0.3245(4) 0.4732(2) 0.0517(12) Uani 1 d . . C6 C 0.2113(4) 0.3763(4) 0.5003(2) 0.0565(13) Uani 1 d . . H6 H 0.2538(4) 0.4454(4) 0.4845(2) 0.068 Uiso 1 calc R . C7 C 0.2372(3) 0.3293(4) 0.5499(2) 0.0538(12) Uani 1 d . . H7 H 0.2957(3) 0.3685(4) 0.5667(2) 0.065 Uiso 1 calc R . C8 C 0.1779(4) 0.2253(4) 0.5750(2) 0.0471(11) Uani 1 d . . C9 C 0.0915(4) 0.1704(4) 0.5479(2) 0.0643(14) Uani 1 d . . H9 H 0.0500(4) 0.0994(4) 0.5634(2) 0.077 Uiso 1 calc R . C10 C 0.0661(4) 0.2195(4) 0.4985(2) 0.0654(14) Uani 1 d . . H10 H 0.0076(4) 0.1805(4) 0.4816(2) 0.079 Uiso 1 calc R . C11 C 0.2027(3) 0.1652(5) 0.6271(2) 0.0503(12) Uani 1 d . . C12 C 0.3151(4) 0.2040(4) 0.7063(2) 0.0523(12) Uani 1 d . . C13 C 0.4003(4) 0.2825(5) 0.7228(2) 0.0694(14) Uani 1 d . . H13 H 0.4221(4) 0.3616(5) 0.7033(2) 0.083 Uiso 1 calc R . C14 C 0.4546(4) 0.2470(6) 0.7678(2) 0.089(2) Uani 1 d . . H14 H 0.5124(4) 0.3019(6) 0.7781(2) 0.107 Uiso 1 calc R . C15 C 0.4241(5) 0.1320(7) 0.7971(2) 0.096(2) Uani 1 d . . H15 H 0.4607(5) 0.1069(7) 0.8273(2) 0.116 Uiso 1 calc R . C16 C 0.3382(5) 0.0544(6) 0.7810(2) 0.098(2) Uani 1 d . . H16 H 0.3167(5) -0.0244(6) 0.8007(2) 0.118 Uiso 1 calc R . C17 C 0.2821(4) 0.0892(5) 0.7363(2) 0.078(2) Uani 1 d . . H17 H 0.2230(4) 0.0359(5) 0.7267(2) 0.094 Uiso 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 O1 0.079(3) 0.047(2) 0.069(2) 0.010(2) 0.004(2) -0.004(2) N1 0.070(3) 0.043(2) 0.046(2) 0.006(2) -0.003(2) 0.003(2) C1 0.062(4) 0.080(3) 0.049(3) 0.003(3) -0.013(3) 0.004(3) C2 0.210(9) 0.204(7) 0.127(6) 0.094(6) -0.103(6) -0.122(6) C3 0.314(11) 0.192(7) 0.061(4) -0.027(5) -0.028(5) 0.159(7) C4 0.096(6) 0.165(6) 0.096(5) 0.037(4) -0.026(4) 0.020(4) C5 0.044(3) 0.058(3) 0.053(3) -0.008(2) -0.005(3) 0.005(2) C6 0.061(4) 0.059(3) 0.050(3) 0.012(2) 0.000(3) -0.010(2) C7 0.047(3) 0.063(3) 0.051(3) 0.008(2) -0.004(2) -0.002(2) C8 0.048(3) 0.046(2) 0.047(3) -0.002(2) 0.003(2) 0.007(2) C9 0.067(4) 0.057(3) 0.068(3) 0.005(3) -0.005(3) -0.011(3) C10 0.057(4) 0.068(3) 0.071(4) 0.003(3) -0.018(3) -0.017(3) C11 0.051(3) 0.046(3) 0.054(3) -0.004(2) 0.009(3) 0.009(2) C12 0.070(4) 0.051(3) 0.036(3) 0.003(2) 0.004(3) 0.015(2) C13 0.068(4) 0.079(3) 0.061(4) 0.015(3) -0.010(3) 0.007(3) C14 0.073(5) 0.125(5) 0.070(4) 0.014(4) -0.013(3) 0.011(4) C15 0.106(6) 0.121(5) 0.062(4) 0.013(4) -0.019(4) 0.036(4) C16 0.145(7) 0.090(4) 0.059(4) 0.026(3) -0.006(4) 0.015(4) C17 0.103(5) 0.072(3) 0.060(4) 0.016(3) -0.004(3) -0.009(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 O1 C11 1.239(4) . ? N1 C11 1.346(5) . ? N1 C12 1.422(5) . ? C1 C3 1.476(6) . ? C1 C2 1.507(6) . ? C1 C5 1.517(6) . ? C1 C4 1.522(6) . ? C5 C10 1.384(5) . ? C5 C6 1.388(5) . ? C6 C7 1.381(5) . ? C7 C8 1.382(5) . ? C8 C9 1.392(5) . ? C8 C11 1.479(5) . ? C9 C10 1.383(5) . ? C12 C13 1.369(6) . ? C12 C17 1.380(5) . ? C13 C14 1.381(6) . ? C14 C15 1.362(7) . ? C15 C16 1.369(7) . ? C16 C17 1.383(6) . ? 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 N1 C12 129.3(4) . . ? C3 C1 C2 109.1(5) . . ? C3 C1 C5 110.9(4) . . ? C2 C1 C5 113.3(4) . . ? C3 C1 C4 107.6(5) . . ? C2 C1 C4 105.1(5) . . ? C5 C1 C4 110.6(4) . . ? C10 C5 C6 115.5(4) . . ? C10 C5 C1 122.4(4) . . ? C6 C5 C1 122.0(4) . . ? C7 C6 C5 122.6(4) . . ? C6 C7 C8 121.3(4) . . ? C7 C8 C9 116.9(4) . . ? C7 C8 C11 124.6(4) . . ? C9 C8 C11 118.5(4) . . ? C10 C9 C8 121.1(4) . . ? C9 C10 C5 122.6(4) . . ? O1 C11 N1 121.8(4) . . ? O1 C11 C8 120.7(4) . . ? N1 C11 C8 117.5(4) . . ? C13 C12 C17 118.5(4) . . ? C13 C12 N1 118.5(4) . . ? C17 C12 N1 122.9(5) . . ? C12 C13 C14 121.5(5) . . ? C15 C14 C13 120.4(6) . . ? C14 C15 C16 118.2(6) . . ? C15 C16 C17 122.3(6) . . ? C12 C17 C16 119.1(5) . . ? _refine_diff_density_max 0.231 _refine_diff_density_min -0.132 _refine_diff_density_rms 0.040 data_gah02 _database_code_CSD 158574 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural 'N-2 methylphenyl 4 t-butylbenzamide' _chemical_formula_analytical ? _chemical_formula_sum 'C18 H21 N O' _chemical_formula_weight 267.36 _chemical_melting_point ? _chemical_compound_source ? 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 10.094(4) _cell_length_b 15.829(10) _cell_length_c 10.054(6) _cell_angle_alpha 93.932(7) _cell_angle_beta 91.00(5) _cell_angle_gamma 89.18(2) _cell_volume 1602.4(15) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.108 _exptl_crystal_density_method ? _exptl_crystal_F_000 576 _exptl_absorpt_coefficient_mu 0.068 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Rigaku R-Axis' _diffrn_measurement_method 'Image plate scans' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3630 _diffrn_reflns_av_R_equivalents 0.0778 _diffrn_reflns_av_sigmaI/netI 0.2605 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 1.29 _diffrn_reflns_theta_max 20.96 _reflns_number_total 2317 _reflns_number_observed 910 _reflns_observed_criterion >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0000P)^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 ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2317 _refine_ls_number_parameters 361 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1963 _refine_ls_R_factor_obs 0.0676 _refine_ls_wR_factor_all 0.1338 _refine_ls_wR_factor_obs 0.0962 _refine_ls_goodness_of_fit_all 0.867 _refine_ls_goodness_of_fit_obs 1.163 _refine_ls_restrained_S_all 0.867 _refine_ls_restrained_S_obs 1.163 _refine_ls_shift/esd_max -0.039 _refine_ls_shift/esd_mean 0.008 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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group O1 O -0.2964(6) -0.0016(4) 0.1609(8) 0.083(3) Uani 1 d . . O2 O 0.1997(6) -0.0050(4) 0.2407(8) 0.090(3) Uani 1 d . . N1 N -0.0794(6) 0.0290(5) 0.2039(8) 0.067(3) Uani 1 d . . H1 H -0.0002(6) 0.0087(5) 0.2095(8) 0.081 Uiso 1 calc R . N2 N 0.4172(6) -0.0383(5) 0.2143(8) 0.055(3) Uani 1 d . . H2 H 0.4945(6) -0.0187(5) 0.2009(8) 0.067 Uiso 1 calc R . C1 C -0.0988(9) 0.1189(7) 0.2130(12) 0.052(3) Uani 1 d . . C2 C -0.1632(10) 0.1617(8) 0.3186(12) 0.064(3) Uani 1 d . . C3 C -0.1667(11) 0.2491(8) 0.3217(17) 0.114(6) Uani 1 d . . H3 H -0.2074(11) 0.2785(8) 0.3935(17) 0.137 Uiso 1 calc R . C4 C -0.1134(14) 0.2952(11) 0.2251(20) 0.133(8) Uani 1 d . . H4 H -0.1215(14) 0.3539(11) 0.2279(20) 0.160 Uiso 1 calc R . C5 C -0.0490(13) 0.2511(10) 0.1261(18) 0.129(7) Uani 1 d . . H5 H -0.0091(13) 0.2804(10) 0.0608(18) 0.155 Uiso 1 calc R . C6 C -0.0403(9) 0.1633(8) 0.1185(11) 0.075(4) Uani 1 d . . H6 H 0.0053(9) 0.1347(8) 0.0492(11) 0.090 Uiso 1 calc R . C7 C -0.2197(10) 0.1125(6) 0.4251(10) 0.110(5) Uani 1 d . . H7A H -0.2065(10) 0.0530(6) 0.4030(10) 0.133 Uiso 1 calc R . H7B H -0.3128(10) 0.1248(6) 0.4323(10) 0.133 Uiso 1 calc R . H7C H -0.1761(10) 0.1280(6) 0.5087(10) 0.133 Uiso 1 calc R . C8 C -0.1827(11) -0.0253(7) 0.1866(11) 0.062(3) Uani 1 d . . C9 C -0.1518(9) -0.1178(7) 0.1987(13) 0.066(4) Uani 1 d . . C10 C -0.0496(11) -0.1427(7) 0.2796(13) 0.090(4) Uani 1 d . . H10 H 0.0058(11) -0.1015(7) 0.3195(13) 0.108 Uiso 1 calc R . C11 C -0.0258(9) -0.2262(8) 0.3039(13) 0.093(5) Uani 1 d . . H11 H 0.0464(9) -0.2399(8) 0.3572(13) 0.111 Uiso 1 calc R . C12 C -0.1066(11) -0.2897(8) 0.2509(13) 0.069(4) Uani 1 d . . C13 C -0.2079(11) -0.2643(7) 0.1665(12) 0.079(4) Uani 1 d . . H13 H -0.2620(11) -0.3053(7) 0.1241(12) 0.094 Uiso 1 calc R . C14 C -0.2309(9) -0.1800(7) 0.1437(11) 0.069(4) Uani 1 d . . H14 H -0.3021(9) -0.1657(7) 0.0895(11) 0.083 Uiso 1 calc R . C15 C -0.0969(14) -0.3834(8) 0.2726(16) 0.099(5) Uani 1 d . . C16 C 0.0070(15) -0.3997(7) 0.3783(15) 0.179(7) Uani 1 d . . H16A H 0.0891(15) -0.3748(7) 0.3556(15) 0.215 Uiso 1 calc R . H16B H 0.0196(15) -0.4596(7) 0.3834(15) 0.215 Uiso 1 calc R . H16C H -0.0216(15) -0.3749(7) 0.4630(15) 0.215 Uiso 1 calc R . C17 C -0.0380(14) -0.4300(6) 0.1537(13) 0.189(8) Uani 1 d . . H17A H 0.0426(14) -0.4031(6) 0.1314(13) 0.227 Uiso 1 calc R . H17B H -0.0994(14) -0.4294(6) 0.0798(13) 0.227 Uiso 1 calc R . H17C H -0.0190(14) -0.4875(6) 0.1733(13) 0.227 Uiso 1 calc R . C18 C -0.2175(11) -0.4216(7) 0.3113(18) 0.279(14) Uani 1 d . . H18A H -0.2520(11) -0.3905(7) 0.3886(18) 0.335 Uiso 1 calc R . H18B H -0.1996(11) -0.4791(7) 0.3315(18) 0.335 Uiso 1 calc R . H18C H -0.2814(11) -0.4208(7) 0.2395(18) 0.335 Uiso 1 calc R . C19 C 0.4049(10) -0.1281(7) 0.2266(14) 0.061(4) Uani 1 d . . C20 C 0.4755(10) -0.1663(8) 0.3216(13) 0.057(3) Uani 1 d . . C21 C 0.4607(12) -0.2541(9) 0.3314(15) 0.095(5) Uani 1 d . . H21 H 0.5088(12) -0.2822(9) 0.3951(15) 0.114 Uiso 1 calc R . C22 C 0.3762(15) -0.2969(9) 0.2475(18) 0.108(7) Uani 1 d . . H22 H 0.3652(15) -0.3546(9) 0.2550(18) 0.130 Uiso 1 calc R . C23 C 0.3070(12) -0.2579(10) 0.1527(17) 0.109(6) Uani 1 d . . H23 H 0.2501(12) -0.2895(10) 0.0959(17) 0.131 Uiso 1 calc R . C24 C 0.3186(10) -0.1718(8) 0.1381(13) 0.088(5) Uani 1 d . . H24 H 0.2713(10) -0.1448(8) 0.0727(13) 0.105 Uiso 1 calc R . C25 C 0.5649(9) -0.1176(6) 0.4211(10) 0.090(4) Uani 1 d . . H25A H 0.6062(9) -0.1560(6) 0.4795(10) 0.109 Uiso 1 calc R . H25B H 0.5133(9) -0.0762(6) 0.4725(10) 0.109 Uiso 1 calc R . H25C H 0.6319(9) -0.0897(6) 0.3744(10) 0.109 Uiso 1 calc R . C26 C 0.3111(11) 0.0175(7) 0.2230(10) 0.063(3) Uani 1 d . . C27 C 0.3478(9) 0.1088(6) 0.2178(10) 0.054(3) Uani 1 d . . C28 C 0.4611(8) 0.1405(6) 0.1653(10) 0.068(4) Uani 1 d . . H28 H 0.5241(8) 0.1028(6) 0.1282(10) 0.081 Uiso 1 calc R . C29 C 0.4833(9) 0.2256(6) 0.1664(11) 0.075(4) Uani 1 d . . H29 H 0.5602(9) 0.2434(6) 0.1278(11) 0.090 Uiso 1 calc R . C30 C 0.3963(10) 0.2874(7) 0.2227(11) 0.058(3) Uani 1 d . . C31 C 0.2836(10) 0.2552(7) 0.2745(11) 0.082(4) Uani 1 d . . H31 H 0.2199(10) 0.2929(7) 0.3097(11) 0.099 Uiso 1 calc R . C32 C 0.2609(8) 0.1696(6) 0.2765(10) 0.062(3) Uani 1 d . . H32 H 0.1858(8) 0.1517(6) 0.3182(10) 0.075 Uiso 1 calc R . C33 C 0.4233(12) 0.3827(7) 0.2238(15) 0.083(4) Uani 1 d . . C34 C 0.4864(13) 0.4084(6) 0.3540(12) 0.139(6) Uani 1 d . . H34A H 0.4287(13) 0.3953(6) 0.4245(12) 0.167 Uiso 1 calc R . H34B H 0.5023(13) 0.4681(6) 0.3591(12) 0.167 Uiso 1 calc R . H34C H 0.5689(13) 0.3783(6) 0.3628(12) 0.167 Uiso 1 calc R . C35 C 0.5151(12) 0.4038(6) 0.1151(13) 0.152(6) Uani 1 d . . H35A H 0.4755(12) 0.3875(6) 0.0299(13) 0.182 Uiso 1 calc R . H35B H 0.5977(12) 0.3738(6) 0.1248(13) 0.182 Uiso 1 calc R . H35C H 0.5308(12) 0.4637(6) 0.1213(13) 0.182 Uiso 1 calc R . C36 C 0.2926(9) 0.4319(6) 0.2047(15) 0.184(8) Uani 1 d . . H36A H 0.2532(9) 0.4142(6) 0.1200(15) 0.221 Uiso 1 calc R . H36B H 0.3101(9) 0.4915(6) 0.2077(15) 0.221 Uiso 1 calc R . H36C H 0.2330(9) 0.4207(6) 0.2746(15) 0.221 Uiso 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 O1 0.041(4) 0.073(5) 0.135(8) 0.014(5) -0.024(5) -0.001(4) O2 0.038(4) 0.070(5) 0.163(9) 0.014(5) 0.033(5) -0.011(4) N1 0.041(5) 0.045(6) 0.116(9) 0.010(6) -0.002(6) 0.001(5) N2 0.042(5) 0.043(6) 0.084(8) 0.019(5) 0.006(5) -0.001(4) C1 0.040(6) 0.066(8) 0.053(10) 0.022(8) 0.002(6) -0.002(6) C2 0.062(8) 0.080(10) 0.049(10) -0.002(8) 0.017(7) -0.010(6) C3 0.071(9) 0.050(11) 0.214(22) -0.034(11) -0.030(10) 0.023(7) C4 0.089(13) 0.057(12) 0.256(28) 0.051(13) -0.059(14) -0.008(9) C5 0.087(11) 0.108(16) 0.204(22) 0.086(14) -0.011(11) -0.018(9) C6 0.077(8) 0.077(9) 0.075(11) 0.031(8) 0.028(7) 0.012(7) C7 0.125(10) 0.130(11) 0.073(11) -0.030(10) 0.034(9) -0.018(9) C8 0.072(8) 0.051(8) 0.060(10) -0.004(7) 0.008(8) 0.004(7) C9 0.035(6) 0.065(9) 0.099(12) 0.027(8) -0.022(7) 0.002(6) C10 0.089(9) 0.040(8) 0.139(14) -0.007(8) -0.035(9) -0.012(6) C11 0.051(7) 0.066(9) 0.160(15) 0.008(9) -0.041(8) -0.006(7) C12 0.059(8) 0.068(9) 0.080(12) 0.006(8) 0.015(8) 0.028(7) C13 0.097(9) 0.039(8) 0.098(13) -0.011(7) -0.016(8) -0.012(7) C14 0.053(7) 0.070(9) 0.081(11) -0.008(8) -0.026(7) -0.008(7) C15 0.133(12) 0.072(11) 0.091(14) 0.015(10) 0.003(10) 0.026(9) C16 0.273(19) 0.066(10) 0.204(21) 0.060(12) -0.034(17) -0.014(11) C17 0.352(23) 0.054(10) 0.161(19) 0.001(11) 0.062(18) 0.031(12) C18 0.116(11) 0.111(12) 0.637(41) 0.178(18) 0.151(18) 0.005(10) C19 0.040(7) 0.069(9) 0.075(12) 0.006(9) -0.001(7) -0.012(7) C20 0.055(7) 0.072(10) 0.045(11) 0.003(8) 0.006(7) 0.004(7) C21 0.089(10) 0.068(12) 0.133(16) 0.034(10) 0.032(10) 0.008(8) C22 0.110(14) 0.046(10) 0.170(22) 0.005(11) 0.033(13) -0.007(9) C23 0.076(10) 0.082(13) 0.162(19) -0.037(11) -0.003(10) -0.010(8) C24 0.058(8) 0.056(9) 0.147(15) -0.012(9) 0.003(9) -0.017(7) C25 0.102(9) 0.103(10) 0.070(11) 0.035(8) -0.003(8) 0.031(8) C26 0.079(9) 0.050(8) 0.058(10) -0.004(7) -0.005(8) 0.003(7) C27 0.042(6) 0.047(7) 0.075(10) 0.012(7) -0.007(6) 0.011(6) C28 0.045(7) 0.063(9) 0.097(11) 0.013(7) 0.027(7) 0.006(6) C29 0.068(8) 0.044(7) 0.117(12) 0.031(7) 0.029(7) -0.002(6) C30 0.048(7) 0.063(8) 0.060(10) -0.003(7) -0.017(7) -0.010(7) C31 0.064(8) 0.058(9) 0.124(13) 0.004(8) 0.000(8) 0.024(7) C32 0.049(7) 0.060(8) 0.078(11) 0.000(7) 0.006(6) -0.001(6) C33 0.106(10) 0.047(9) 0.093(14) -0.007(8) -0.017(9) -0.013(7) C34 0.279(18) 0.058(9) 0.082(13) 0.003(9) -0.005(13) -0.054(10) C35 0.235(16) 0.065(9) 0.161(17) 0.020(10) 0.069(13) -0.031(10) C36 0.088(9) 0.061(10) 0.406(26) 0.044(12) -0.041(13) 0.015(7) _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 O1 C8 1.231(10) . ? O2 C26 1.204(10) . ? N1 C8 1.363(10) . ? N1 C1 1.431(10) . ? N2 C26 1.379(10) . ? N2 C19 1.442(11) . ? C1 C6 1.367(11) . ? C1 C2 1.386(11) . ? C2 C3 1.381(13) . ? C2 C7 1.493(12) . ? C3 C4 1.38(2) . ? C4 C5 1.35(2) . ? C5 C6 1.389(14) . ? C8 C9 1.505(12) . ? C9 C14 1.358(11) . ? C9 C10 1.373(12) . ? C10 C11 1.377(12) . ? C11 C12 1.377(13) . ? C12 C13 1.389(13) . ? C12 C15 1.516(14) . ? C13 C14 1.385(11) . ? C15 C18 1.438(14) . ? C15 C17 1.489(15) . ? C15 C16 1.51(2) . ? C19 C20 1.353(13) . ? C19 C24 1.391(13) . ? C20 C21 1.410(13) . ? C20 C25 1.514(12) . ? C21 C22 1.34(2) . ? C22 C23 1.35(2) . ? C23 C24 1.387(14) . ? C26 C27 1.502(11) . ? C27 C28 1.383(10) . ? C27 C32 1.400(10) . ? C28 C29 1.368(10) . ? C29 C30 1.402(10) . ? C30 C31 1.378(11) . ? C30 C33 1.536(12) . ? C31 C32 1.379(11) . ? C33 C34 1.479(14) . ? C33 C35 1.503(13) . ? C33 C36 1.538(12) . ? 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 C8 N1 C1 121.9(8) . . ? C26 N2 C19 123.2(8) . . ? C6 C1 C2 120.0(10) . . ? C6 C1 N1 117.1(11) . . ? C2 C1 N1 122.7(10) . . ? C3 C2 C1 117.4(11) . . ? C3 C2 C7 123.4(13) . . ? C1 C2 C7 119.2(11) . . ? C4 C3 C2 123.9(16) . . ? C5 C4 C3 116.7(18) . . ? C4 C5 C6 122.1(17) . . ? C1 C6 C5 119.9(11) . . ? O1 C8 N1 122.8(10) . . ? O1 C8 C9 120.4(10) . . ? N1 C8 C9 116.8(9) . . ? C14 C9 C10 116.6(10) . . ? C14 C9 C8 122.4(10) . . ? C10 C9 C8 120.6(11) . . ? C9 C10 C11 122.6(11) . . ? C10 C11 C12 121.5(11) . . ? C11 C12 C13 115.6(11) . . ? C11 C12 C15 127.7(13) . . ? C13 C12 C15 116.7(13) . . ? C14 C13 C12 122.1(11) . . ? C9 C14 C13 121.6(10) . . ? C18 C15 C17 111.8(14) . . ? C18 C15 C16 107.3(13) . . ? C17 C15 C16 100.9(11) . . ? C18 C15 C12 115.6(11) . . ? C17 C15 C12 109.9(11) . . ? C16 C15 C12 110.4(12) . . ? C20 C19 C24 122.7(12) . . ? C20 C19 N2 120.0(12) . . ? C24 C19 N2 117.3(13) . . ? C19 C20 C21 118.6(12) . . ? C19 C20 C25 122.3(12) . . ? C21 C20 C25 119.1(14) . . ? C22 C21 C20 119.2(15) . . ? C23 C22 C21 121.5(16) . . ? C22 C23 C24 121.6(16) . . ? C23 C24 C19 116.4(13) . . ? O2 C26 N2 122.6(10) . . ? O2 C26 C27 123.0(10) . . ? N2 C26 C27 114.3(9) . . ? C28 C27 C32 115.3(9) . . ? C28 C27 C26 127.4(9) . . ? C32 C27 C26 117.3(9) . . ? C29 C28 C27 121.9(9) . . ? C28 C29 C30 123.5(8) . . ? C31 C30 C29 114.1(10) . . ? C31 C30 C33 123.1(11) . . ? C29 C30 C33 122.8(9) . . ? C30 C31 C32 123.1(10) . . ? C31 C32 C27 121.9(9) . . ? C34 C33 C35 108.5(11) . . ? C34 C33 C36 110.7(11) . . ? C35 C33 C36 107.8(12) . . ? C34 C33 C30 107.3(11) . . ? C35 C33 C30 112.5(10) . . ? C36 C33 C30 110.0(9) . . ? _refine_diff_density_max 0.186 _refine_diff_density_min -0.174 _refine_diff_density_rms 0.043 data_gah03 _database_code_CSD 158575 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common 'N-2,6 dimethylphenyl 4 t-butylbenzamide' _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C19 H23 N O' _chemical_formula_weight 281.38 _chemical_melting_point ? _chemical_compound_source ? 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 P212121 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 9.7512(14) _cell_length_b 28.576(4) _cell_length_c 6.0247(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1678.8(4) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 1.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.113 _exptl_crystal_density_method ? _exptl_crystal_F_000 608 _exptl_absorpt_coefficient_mu 0.068 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Rigaku R-Axis' _diffrn_measurement_method 'Image plate scans' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8661 _diffrn_reflns_av_R_equivalents 0.0512 _diffrn_reflns_av_sigmaI/netI 0.0338 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -34 _diffrn_reflns_limit_k_max 30 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 2.21 _diffrn_reflns_theta_max 25.24 _reflns_number_total 2864 _reflns_number_observed 2828 _reflns_observed_criterion >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0705P)^2^+0.2598P] 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 ? _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 3.31(227) _refine_ls_number_reflns 2864 _refine_ls_number_parameters 268 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0544 _refine_ls_R_factor_obs 0.0533 _refine_ls_wR_factor_all 0.1428 _refine_ls_wR_factor_obs 0.1419 _refine_ls_goodness_of_fit_all 1.173 _refine_ls_goodness_of_fit_obs 1.174 _refine_ls_restrained_S_all 1.173 _refine_ls_restrained_S_obs 1.174 _refine_ls_shift/esd_max -0.024 _refine_ls_shift/esd_mean 0.002 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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group O1 O 0.7112(2) 0.24375(5) -0.1159(3) 0.0562(5) Uani 1 d . . N1 N 0.4970(2) 0.26773(6) -0.0262(4) 0.0476(5) Uani 1 d . . C1 C 0.5993(2) 0.34512(8) 0.0297(5) 0.0590(7) Uani 1 d . . C2 C 0.6076(3) 0.39200(10) -0.0389(8) 0.0820(10) Uani 1 d . . C3 C 0.5372(4) 0.40775(10) -0.2219(8) 0.0883(11) Uani 1 d . . C4 C 0.4575(3) 0.37797(11) -0.3423(6) 0.0767(9) Uani 1 d . . C5 C 0.4454(3) 0.33082(9) -0.2832(5) 0.0555(6) Uani 1 d . . C6 C 0.5156(2) 0.31544(7) -0.0961(4) 0.0473(5) Uani 1 d . . C7 C 0.6785(3) 0.32863(13) 0.2274(6) 0.0786(9) Uani 1 d . . C8 C 0.3600(4) 0.29843(13) -0.4194(6) 0.0775(8) Uani 1 d . . C9 C 0.5966(2) 0.23489(8) -0.0386(4) 0.0445(5) Uani 1 d . . C10 C 0.5632(2) 0.18752(7) 0.0521(4) 0.0452(5) Uani 1 d . . C11 C 0.4613(3) 0.17938(9) 0.2047(5) 0.0594(6) Uani 1 d . . C12 C 0.4415(3) 0.13497(9) 0.2935(5) 0.0642(7) Uani 1 d . . C13 C 0.5231(2) 0.09730(8) 0.2321(4) 0.0493(5) Uani 1 d . . C14 C 0.6232(3) 0.10579(8) 0.0743(5) 0.0587(6) Uani 1 d . . C15 C 0.6452(3) 0.14986(8) -0.0149(5) 0.0549(6) Uani 1 d . . C16 C 0.5057(3) 0.04842(8) 0.3341(5) 0.0585(6) Uani 1 d . . C17 C 0.6384(4) 0.03430(14) 0.4493(8) 0.0883(11) Uani 1 d . . C18 C 0.4736(6) 0.01361(12) 0.1497(8) 0.1029(14) Uani 1 d . . C19 C 0.3914(4) 0.04701(14) 0.5078(9) 0.0958(13) Uani 1 d . . H1 H 0.6695(36) 0.4128(12) 0.0598(70) 0.094(8) Uiso 1 d . . H2 H 0.5447(33) 0.4428(13) -0.2733(63) 0.094(8) Uiso 1 d . . H3 H 0.4031(36) 0.3868(12) -0.4871(72) 0.099(12) Uiso 1 d . . H4 H 0.7651(54) 0.3145(17) 0.1892(100) 0.147(10) Uiso 1 d . . H5 H 0.6848(49) 0.3530(16) 0.3572(104) 0.147(10) Uiso 1 d . . H6 H 0.6419(54) 0.2983(17) 0.3089(102) 0.147(10) Uiso 1 d . . H7 H 0.4224(48) 0.2674(15) -0.4572(85) 0.128(9) Uiso 1 d . . H8 H 0.2813(48) 0.2807(15) -0.3376(89) 0.128(9) Uiso 1 d . . H9 H 0.3445(47) 0.3082(15) -0.5729(90) 0.128(9) Uiso 1 d . . H10 H 0.4167(28) 0.2596(9) 0.0185(46) 0.048(7) Uiso 1 d . . H11 H 0.3987(30) 0.2062(11) 0.2616(57) 0.080(4) Uiso 1 d . . H12 H 0.3681(31) 0.1295(10) 0.4009(62) 0.080(4) Uiso 1 d . . H13 H 0.6927(32) 0.0791(11) 0.0170(58) 0.080(4) Uiso 1 d . . H14 H 0.7137(32) 0.1565(10) -0.1286(61) 0.080(4) Uiso 1 d . . H15 H 0.6583(45) 0.0586(14) 0.5940(88) 0.124(8) Uiso 1 d . . H16 H 0.7160(47) 0.0315(14) 0.3164(88) 0.124(8) Uiso 1 d . . H17 H 0.6301(41) -0.0033(15) 0.5016(83) 0.124(8) Uiso 1 d . . H18 H 0.5658(44) 0.0126(17) 0.0129(91) 0.134(9) Uiso 1 d . . H19 H 0.4706(47) -0.0182(17) 0.2182(82) 0.134(9) Uiso 1 d . . H20 H 0.3665(49) 0.0220(16) 0.0801(95) 0.134(9) Uiso 1 d . . H21 H 0.4216(37) 0.0722(14) 0.6211(74) 0.100(6) Uiso 1 d . . H22 H 0.2945(40) 0.0555(12) 0.4217(69) 0.100(6) Uiso 1 d . . H23 H 0.3829(36) 0.0149(14) 0.5802(73) 0.100(6) Uiso 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 O1 0.0390(8) 0.0510(9) 0.0786(12) 0.0017(8) 0.0109(8) -0.0029(7) N1 0.0362(9) 0.0402(9) 0.0664(12) 0.0022(8) 0.0013(9) -0.0017(7) C1 0.0504(13) 0.0501(13) 0.077(2) -0.0164(12) 0.0063(13) -0.0035(10) C2 0.074(2) 0.0484(14) 0.124(3) -0.024(2) 0.017(2) -0.0101(13) C3 0.089(2) 0.0457(15) 0.130(3) 0.007(2) 0.025(2) 0.0061(15) C4 0.078(2) 0.064(2) 0.089(2) 0.022(2) 0.017(2) 0.0161(15) C5 0.0527(12) 0.0558(13) 0.0581(14) 0.0042(11) 0.0069(12) 0.0046(11) C6 0.0434(11) 0.0377(10) 0.0607(13) -0.0064(10) 0.0058(10) -0.0012(9) C7 0.065(2) 0.090(2) 0.080(2) -0.028(2) -0.013(2) -0.002(2) C8 0.077(2) 0.092(2) 0.063(2) 0.000(2) -0.013(2) -0.003(2) C9 0.0363(11) 0.0444(11) 0.0527(12) -0.0019(10) 0.0007(9) -0.0018(8) C10 0.0410(10) 0.0414(10) 0.0532(12) 0.0000(9) -0.0016(10) 0.0004(9) C11 0.0530(13) 0.0494(12) 0.076(2) 0.0062(12) 0.0178(13) 0.0087(11) C12 0.0599(14) 0.0551(14) 0.078(2) 0.0137(13) 0.0213(14) 0.0084(12) C13 0.0453(12) 0.0474(11) 0.0551(13) 0.0034(10) 0.0009(10) 0.0003(10) C14 0.0587(14) 0.0459(12) 0.072(2) -0.0013(12) 0.0146(13) 0.0053(11) C15 0.0523(13) 0.0473(12) 0.065(2) 0.0002(11) 0.0153(12) 0.0025(10) C16 0.0563(13) 0.0515(13) 0.068(2) 0.0118(11) 0.0006(13) 0.0012(11) C17 0.077(2) 0.086(2) 0.102(3) 0.027(2) -0.011(2) 0.010(2) C18 0.145(4) 0.059(2) 0.105(3) 0.008(2) -0.018(3) -0.032(2) C19 0.091(2) 0.077(2) 0.120(3) 0.047(2) 0.032(2) 0.010(2) _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 O1 C9 1.237(3) . ? N1 C9 1.352(3) . ? N1 C6 1.438(3) . ? C1 C6 1.400(3) . ? C1 C2 1.404(4) . ? C1 C7 1.496(5) . ? C2 C3 1.374(6) . ? C3 C4 1.362(5) . ? C4 C5 1.399(4) . ? C5 C6 1.390(4) . ? C5 C8 1.492(4) . ? C9 C10 1.496(3) . ? C10 C11 1.374(3) . ? C10 C15 1.400(3) . ? C11 C12 1.391(4) . ? C12 C13 1.388(3) . ? C13 C14 1.384(3) . ? C13 C16 1.535(3) . ? C14 C15 1.386(3) . ? C16 C17 1.523(4) . ? C16 C18 1.524(5) . ? C16 C19 1.529(5) . ? 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 C9 N1 C6 123.4(2) . . ? C6 C1 C2 116.9(3) . . ? C6 C1 C7 122.8(2) . . ? C2 C1 C7 120.3(3) . . ? C3 C2 C1 121.3(3) . . ? C4 C3 C2 120.5(3) . . ? C3 C4 C5 120.9(3) . . ? C6 C5 C4 118.0(3) . . ? C6 C5 C8 121.7(2) . . ? C4 C5 C8 120.3(3) . . ? C5 C6 C1 122.3(2) . . ? C5 C6 N1 118.4(2) . . ? C1 C6 N1 119.3(2) . . ? O1 C9 N1 121.9(2) . . ? O1 C9 C10 121.3(2) . . ? N1 C9 C10 116.8(2) . . ? C11 C10 C15 118.4(2) . . ? C11 C10 C9 123.7(2) . . ? C15 C10 C9 117.8(2) . . ? C10 C11 C12 120.8(2) . . ? C13 C12 C11 121.7(2) . . ? C14 C13 C12 116.8(2) . . ? C14 C13 C16 120.8(2) . . ? C12 C13 C16 122.4(2) . . ? C13 C14 C15 122.3(2) . . ? C14 C15 C10 119.9(2) . . ? C17 C16 C18 109.5(3) . . ? C17 C16 C19 107.5(3) . . ? C18 C16 C19 109.4(3) . . ? C17 C16 C13 109.2(2) . . ? C18 C16 C13 109.0(2) . . ? C19 C16 C13 112.2(2) . . ? _refine_diff_density_max 0.165 _refine_diff_density_min -0.159 _refine_diff_density_rms 0.037 data_gah04 _database_code_CSD 158576 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'N-2,6 diethylphenyl 4 t-butylbenzamide' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H27 N O' _chemical_formula_weight 309.44 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 Pna21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x+1/2, y+1/2, z+1/2' 'x+1/2, -y+1/2, z' _cell_length_a 27.4017(6) _cell_length_b 20.5783(3) _cell_length_c 9.9928(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 5634.7(2) _cell_formula_units_Z 12 _cell_measurement_temperature 160(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.02 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.094 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2016 _exptl_absorpt_coefficient_mu 0.066 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.9740 _exptl_absorpt_correction_T_max 0.9993 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 160(2) _diffrn_radiation_wavelength 0.69560 _diffrn_radiation_type ? _diffrn_radiation_source 'Synchrotron' _diffrn_radiation_monochromator ? _diffrn_measurement_device_type 'Station 9.8, Daresbury labs.' _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 7987 _diffrn_reflns_av_R_equivalents 0.3091 _diffrn_reflns_av_sigmaI/netI 0.3259 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 1.21 _diffrn_reflns_theta_max 19.33 _reflns_number_total 3146 _reflns_number_gt 2231 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _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^)+(0.2867P)^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 10(10) _refine_ls_number_reflns 3146 _refine_ls_number_parameters 456 _refine_ls_number_restraints 494 _refine_ls_R_factor_all 0.2102 _refine_ls_R_factor_gt 0.1802 _refine_ls_wR_factor_ref 0.4368 _refine_ls_wR_factor_gt 0.4246 _refine_ls_goodness_of_fit_ref 1.104 _refine_ls_restrained_S_all 1.491 _refine_ls_shift/su_max 0.150 _refine_ls_shift/su_mean 0.017 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 O1 O 0.4882(7) 0.4962(9) 0.246(2) 0.094(9) Uani 1 1 d DU . . N1 N 0.5069(4) 0.4862(5) 0.4825(13) 0.074(7) Uani 1 1 d DU . . H1 H 0.5036 0.5046 0.5615 0.089 Uiso 1 1 calc R . . C1 C 0.5839(4) 0.4312(5) 0.4522(13) 0.120(10) Uani 1 1 d RDU . . C2 C 0.6106(4) 0.3738(5) 0.4457(13) 0.139(12) Uani 1 1 d RDU . . H2 H 0.6452 0.3754 0.4383 0.167 Uiso 1 1 calc R . . C3 C 0.5868(4) 0.3142(5) 0.4501(13) 0.140(12) Uani 1 1 d RDU . . H3 H 0.6051 0.2751 0.4457 0.168 Uiso 1 1 calc R . . C4 C 0.5363(4) 0.3120(5) 0.4608(13) 0.123(11) Uani 1 1 d RDU . . H4 H 0.5200 0.2712 0.4638 0.147 Uiso 1 1 calc R . . C5 C 0.5095(4) 0.3693(5) 0.4673(13) 0.095(9) Uani 1 1 d RDU . . C6 C 0.5333(4) 0.4289(5) 0.4629(13) 0.104(9) Uani 1 1 d RDU . . C7 C 0.4849(4) 0.5135(6) 0.3597(18) 0.077(9) Uani 1 1 d DU . . C8 C 0.4541(4) 0.5732(6) 0.4052(18) 0.066(8) Uani 1 1 d RDU . . C9 C 0.4445(4) 0.5903(6) 0.5372(18) 0.085(10) Uani 1 1 d RDU . . H9 H 0.4567 0.5642 0.6082 0.102 Uiso 1 1 calc R . . C10 C 0.4170(4) 0.6454(6) 0.5652(18) 0.103(11) Uani 1 1 d RDU . . H10 H 0.4104 0.6570 0.6554 0.124 Uiso 1 1 calc R . . C11 C 0.3991(4) 0.6835(6) 0.4613(18) 0.110(10) Uani 1 1 d RDU . . C12 C 0.4088(4) 0.6664(6) 0.3293(18) 0.083(10) Uani 1 1 d RDU . . H12 H 0.3966 0.6925 0.2583 0.099 Uiso 1 1 calc R . . C13 C 0.4363(4) 0.6113(6) 0.3012(18) 0.080(9) Uani 1 1 d RDU . . H13 H 0.4429 0.5997 0.2110 0.096 Uiso 1 1 calc R . . C14 C 0.6096(13) 0.4950(13) 0.4475(15) 0.161(14) Uani 1 1 d DU . . H14A H 0.5852 0.5303 0.4398 0.193 Uiso 1 1 calc R . . H14B H 0.6278 0.5015 0.5321 0.193 Uiso 1 1 calc R . . C15 C 0.644(3) 0.499(4) 0.334(7) 0.26(3) Uiso 1 1 d DU . . H15A H 0.6768 0.4873 0.3638 0.310 Uiso 1 1 calc R . . H15B H 0.6442 0.5434 0.2982 0.310 Uiso 1 1 calc R . . H15C H 0.6336 0.4689 0.2631 0.310 Uiso 1 1 calc R . . C16 C 0.4561(7) 0.3639(12) 0.4784(15) 0.082(9) Uani 1 1 d DU . . H16A H 0.4446 0.3243 0.4321 0.099 Uiso 1 1 calc R . . H16B H 0.4403 0.4021 0.4366 0.099 Uiso 1 1 calc R . . C17 C 0.4435(15) 0.3607(19) 0.624(3) 0.106(13) Uiso 1 1 d DU . . H17A H 0.4089 0.3711 0.6357 0.127 Uiso 1 1 calc R . . H17B H 0.4634 0.3921 0.6733 0.127 Uiso 1 1 calc R . . H17C H 0.4500 0.3168 0.6575 0.127 Uiso 1 1 calc R . . C18 C 0.3697(6) 0.7423(10) 0.493(4) 0.100(11) Uani 1 1 d DU . . C19 C 0.3186(14) 0.716(3) 0.512(7) 0.21(3) Uiso 1 1 d DU . . H19A H 0.3075 0.6954 0.4291 0.253 Uiso 1 1 calc R . . H19B H 0.2965 0.7515 0.5356 0.253 Uiso 1 1 calc R . . H19C H 0.3187 0.6836 0.5844 0.253 Uiso 1 1 calc R . . C20 C 0.390(2) 0.778(3) 0.614(5) 0.155(18) Uiso 1 1 d DU . . H20A H 0.4065 0.7466 0.6733 0.187 Uiso 1 1 calc R . . H20B H 0.3634 0.7988 0.6631 0.187 Uiso 1 1 calc R . . H20C H 0.4135 0.8108 0.5848 0.187 Uiso 1 1 calc R . . C21 C 0.3648(19) 0.790(2) 0.379(5) 0.141(17) Uiso 1 1 d DU . . H21A H 0.3973 0.8047 0.3523 0.169 Uiso 1 1 calc R . . H21B H 0.3452 0.8269 0.4082 0.169 Uiso 1 1 calc R . . H21C H 0.3489 0.7683 0.3034 0.169 Uiso 1 1 calc R . . O2 O 0.3282(9) 0.2827(12) 0.727(3) 0.116(11) Uani 1 1 d DU . . N2 N 0.3403(4) 0.2713(5) 0.9840(14) 0.063(7) Uani 1 1 d DU . . H2A H 0.3308 0.2819 1.0652 0.076 Uiso 1 1 calc R . . C31 C 0.4273(4) 0.2482(5) 0.9634(14) 0.102(9) Uani 1 1 d RDU . . C32 C 0.4662(4) 0.2052(5) 0.9559(14) 0.126(11) Uani 1 1 d RDU . . H32 H 0.4988 0.2211 0.9588 0.151 Uiso 1 1 calc R . . C33 C 0.4576(4) 0.1389(5) 0.9442(14) 0.134(12) Uani 1 1 d RDU . . H33 H 0.4843 0.1095 0.9391 0.160 Uiso 1 1 calc R . . C34 C 0.4100(4) 0.1156(5) 0.9400(14) 0.112(11) Uani 1 1 d RDU . . H34 H 0.4042 0.0703 0.9320 0.135 Uiso 1 1 calc R . . C35 C 0.3711(4) 0.1586(5) 0.9476(14) 0.095(10) Uani 1 1 d RDU . . C36 C 0.3797(4) 0.2250(5) 0.9593(14) 0.092(9) Uani 1 1 d RDU . . C37 C 0.3194(4) 0.2969(5) 0.8722(18) 0.062(8) Uani 1 1 d DU . . C38 C 0.2815(4) 0.3478(5) 0.9108(18) 0.056(8) Uani 1 1 d RDU . . C39 C 0.2679(4) 0.3611(5) 1.0419(18) 0.086(10) Uani 1 1 d RDU . . H39 H 0.2825 0.3380 1.1137 0.103 Uiso 1 1 calc R . . C40 C 0.2328(4) 0.4082(5) 1.0680(18) 0.107(11) Uani 1 1 d RDU . . H40 H 0.2235 0.4173 1.1577 0.128 Uiso 1 1 calc R . . C41 C 0.2114(4) 0.4421(5) 0.9630(18) 0.086(9) Uani 1 1 d RDU . . C42 C 0.2250(4) 0.4288(5) 0.8318(18) 0.094(10) Uani 1 1 d RDU . . H42 H 0.2103 0.4519 0.7600 0.113 Uiso 1 1 calc R . . C43 C 0.2600(4) 0.3816(5) 0.8057(18) 0.084(9) Uani 1 1 d RDU . . H43 H 0.2693 0.3725 0.7161 0.101 Uiso 1 1 calc R . . C44 C 0.4357(12) 0.3215(10) 0.9761(15) 0.101(10) Uani 1 1 d DU . . H44A H 0.4660 0.3337 0.9282 0.121 Uiso 1 1 calc R . . H44B H 0.4081 0.3452 0.9343 0.121 Uiso 1 1 calc R . . C45 C 0.4398(17) 0.341(2) 1.121(3) 0.116(14) Uiso 1 1 d DU . . H45A H 0.4415 0.3013 1.1767 0.139 Uiso 1 1 calc R . . H45B H 0.4112 0.3662 1.1473 0.139 Uiso 1 1 calc R . . H45C H 0.4695 0.3664 1.1346 0.139 Uiso 1 1 calc R . . C46 C 0.3216(11) 0.1289(16) 0.9418(16) 0.121(12) Uani 1 1 d DU . . H46A H 0.2999 0.1592 0.8933 0.146 Uiso 1 1 calc R . . H46B H 0.3239 0.0888 0.8874 0.146 Uiso 1 1 calc R . . C47 C 0.2980(19) 0.112(3) 1.069(4) 0.149(18) Uiso 1 1 d DU . . H47A H 0.2625 0.1103 1.0560 0.179 Uiso 1 1 calc R . . H47B H 0.3058 0.1450 1.1362 0.179 Uiso 1 1 calc R . . H47C H 0.3097 0.0695 1.0991 0.179 Uiso 1 1 calc R . . C48 C 0.1733(7) 0.4936(10) 0.987(4) 0.116(11) Uani 1 1 d DU . . C49 C 0.196(2) 0.554(2) 0.928(7) 0.19(2) Uiso 1 1 d DU . . H49A H 0.1708 0.5782 0.8768 0.234 Uiso 1 1 calc R . . H49B H 0.2226 0.5424 0.8678 0.234 Uiso 1 1 calc R . . H49C H 0.2082 0.5821 0.9997 0.234 Uiso 1 1 calc R . . C50 C 0.1353(17) 0.480(2) 0.881(5) 0.139(17) Uiso 1 1 d DU . . H50A H 0.1092 0.4530 0.9190 0.166 Uiso 1 1 calc R . . H50B H 0.1506 0.4565 0.8061 0.166 Uiso 1 1 calc R . . H50C H 0.1216 0.5209 0.8484 0.166 Uiso 1 1 calc R . . C51 C 0.1520(19) 0.500(3) 1.125(4) 0.145(17) Uiso 1 1 d DU . . H51A H 0.1307 0.4632 1.1442 0.174 Uiso 1 1 calc R . . H51B H 0.1330 0.5407 1.1307 0.174 Uiso 1 1 calc R . . H51C H 0.1785 0.5017 1.1914 0.174 Uiso 1 1 calc R . . O3 O 0.3304(8) 0.2650(11) 1.236(3) 0.125(11) Uani 1 1 d DU . . N3 N 0.3212(5) 0.2875(6) 1.4836(12) 0.068(7) Uani 1 1 d DU . . H3A H 0.3338 0.2820 1.5638 0.081 Uiso 1 1 calc R . . C61 C 0.2817(5) 0.3921(6) 1.4429(12) 0.111(10) Uani 1 1 d RDU . . C62 C 0.2394(5) 0.4295(6) 1.4390(12) 0.101(10) Uani 1 1 d RDU . . H62 H 0.2416 0.4754 1.4310 0.121 Uiso 1 1 calc R . . C63 C 0.1940(5) 0.3997(6) 1.4466(12) 0.120(11) Uani 1 1 d RDU . . H63 H 0.1651 0.4252 1.4439 0.144 Uiso 1 1 calc R . . C64 C 0.1908(5) 0.3325(6) 1.4582(12) 0.137(12) Uani 1 1 d RDU . . H64 H 0.1597 0.3122 1.4634 0.165 Uiso 1 1 calc R . . C65 C 0.2330(5) 0.2951(6) 1.4622(12) 0.114(10) Uani 1 1 d RDU . . C66 C 0.2784(5) 0.3249(6) 1.4545(12) 0.094(9) Uani 1 1 d RDU . . C67 C 0.3396(5) 0.2616(5) 1.368(2) 0.082(9) Uani 1 1 d DU . . C68 C 0.3830(5) 0.2163(5) 1.410(2) 0.074(9) Uani 1 1 d RDU . . C69 C 0.3966(5) 0.2041(5) 1.541(2) 0.071(9) Uani 1 1 d RDU . . H69 H 0.3779 0.2215 1.6130 0.085 Uiso 1 1 calc R . . C70 C 0.4375(5) 0.1663(5) 1.568(2) 0.087(10) Uani 1 1 d RDU . . H70 H 0.4468 0.1580 1.6582 0.105 Uiso 1 1 calc R . . C71 C 0.4648(5) 0.1407(5) 1.464(2) 0.078(8) Uani 1 1 d RDU . . C72 C 0.4512(5) 0.1529(5) 1.332(2) 0.086(10) Uani 1 1 d RDU . . H72 H 0.4698 0.1355 1.2603 0.103 Uiso 1 1 calc R . . C73 C 0.4102(5) 0.1907(5) 1.305(2) 0.079(9) Uani 1 1 d RDU . . H73 H 0.4009 0.1990 1.2151 0.095 Uiso 1 1 calc R . . C74 C 0.3298(10) 0.4251(19) 1.4345(14) 0.121(13) Uani 1 1 d DU . . H74A H 0.3332 0.4462 1.3459 0.145 Uiso 1 1 calc R . . H74B H 0.3562 0.3927 1.4439 0.145 Uiso 1 1 calc R . . C75 C 0.334(3) 0.476(3) 1.543(6) 0.23(3) Uiso 1 1 d DU . . H75A H 0.3584 0.5083 1.5166 0.275 Uiso 1 1 calc R . . H75B H 0.3449 0.4546 1.6264 0.275 Uiso 1 1 calc R . . H75C H 0.3026 0.4965 1.5574 0.275 Uiso 1 1 calc R . . C76 C 0.2265(13) 0.2241(12) 1.4742(14) 0.127(12) Uani 1 1 d DU . . H76A H 0.1937 0.2123 1.4404 0.153 Uiso 1 1 calc R . . H76B H 0.2509 0.2020 1.4173 0.153 Uiso 1 1 calc R . . C77 C 0.231(2) 0.201(3) 1.612(4) 0.155(18) Uiso 1 1 d DU . . H77A H 0.2420 0.1554 1.6107 0.186 Uiso 1 1 calc R . . H77B H 0.2000 0.2044 1.6575 0.186 Uiso 1 1 calc R . . H77C H 0.2558 0.2272 1.6586 0.186 Uiso 1 1 calc R . . C78 C 0.5087(7) 0.1003(7) 1.493(4) 0.077(9) Uani 1 1 d DU . . C79 C 0.5464(14) 0.131(2) 1.582(4) 0.117(14) Uiso 1 1 d DU . . H79A H 0.5577 0.0994 1.6482 0.140 Uiso 1 1 calc R . . H79B H 0.5319 0.1685 1.6285 0.140 Uiso 1 1 calc R . . H79C H 0.5741 0.1460 1.5280 0.140 Uiso 1 1 calc R . . C80 C 0.4988(16) 0.0407(16) 1.572(4) 0.115(14) Uiso 1 1 d DU . . H80A H 0.5294 0.0247 1.6112 0.137 Uiso 1 1 calc R . . H80B H 0.4849 0.0072 1.5140 0.137 Uiso 1 1 calc R . . H80C H 0.4757 0.0508 1.6442 0.137 Uiso 1 1 calc R . . C81 C 0.539(2) 0.092(3) 1.366(5) 0.164(19) Uiso 1 1 d DU . . H81A H 0.5734 0.0871 1.3901 0.197 Uiso 1 1 calc R . . H81B H 0.5350 0.1308 1.3096 0.197 Uiso 1 1 calc R . . H81C H 0.5278 0.0537 1.3174 0.197 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 O1 0.18(3) 0.069(13) 0.031(13) -0.041(10) -0.038(17) 0.056(15) N1 0.072(14) 0.024(10) 0.13(2) 0.001(14) 0.008(17) 0.031(10) C1 0.075(16) 0.034(12) 0.25(3) 0.04(2) 0.03(2) 0.029(14) C2 0.059(17) 0.082(18) 0.28(3) 0.04(2) 0.02(2) 0.006(16) C3 0.080(19) 0.070(17) 0.27(3) 0.03(2) 0.04(3) 0.001(17) C4 0.064(17) 0.067(16) 0.24(3) 0.04(2) 0.02(2) 0.000(15) C5 0.048(14) 0.029(12) 0.21(2) 0.025(18) 0.033(19) 0.004(12) C6 0.075(16) 0.047(14) 0.19(2) 0.019(19) 0.02(2) -0.002(14) C7 0.093(19) 0.038(14) 0.10(2) -0.013(15) 0.008(19) 0.021(14) C8 0.088(17) 0.046(13) 0.065(18) 0.020(14) 0.034(16) -0.011(14) C9 0.10(2) 0.040(15) 0.11(2) -0.029(15) 0.03(2) -0.025(15) C10 0.12(2) 0.08(2) 0.12(3) -0.013(18) 0.02(2) -0.003(18) C11 0.12(2) 0.101(18) 0.11(2) 0.009(19) 0.04(2) -0.003(17) C12 0.13(2) 0.080(18) 0.043(19) 0.042(16) 0.032(19) 0.013(18) C13 0.14(2) 0.069(17) 0.035(18) 0.043(15) 0.019(19) -0.019(17) C14 0.10(2) 0.10(2) 0.28(4) 0.06(3) 0.04(3) 0.04(2) C16 0.051(15) 0.031(11) 0.16(3) 0.034(19) 0.04(2) -0.014(12) C18 0.10(2) 0.086(18) 0.11(2) -0.02(2) 0.01(2) 0.050(16) O2 0.11(2) 0.12(2) 0.12(2) 0.090(19) -0.049(19) -0.016(16) N2 0.043(12) 0.035(10) 0.111(19) -0.016(14) -0.044(15) 0.027(10) C31 0.074(17) 0.069(15) 0.16(2) 0.021(19) -0.063(19) 0.015(14) C32 0.078(19) 0.112(19) 0.19(3) 0.03(2) -0.05(2) 0.042(18) C33 0.13(2) 0.093(19) 0.18(3) 0.02(2) 0.00(3) 0.03(2) C34 0.11(2) 0.076(18) 0.15(3) 0.00(2) 0.02(2) 0.040(18) C35 0.105(19) 0.046(14) 0.13(2) -0.008(17) 0.00(2) 0.015(14) C36 0.077(16) 0.058(14) 0.14(2) 0.018(17) -0.035(19) -0.021(13) C37 0.052(16) 0.033(13) 0.10(2) -0.002(15) -0.064(17) 0.007(13) C38 0.043(14) 0.035(13) 0.09(2) 0.000(14) -0.016(15) 0.010(12) C39 0.09(2) 0.025(13) 0.14(3) -0.037(16) 0.01(2) 0.010(14) C40 0.10(2) 0.070(19) 0.15(3) -0.030(19) 0.02(2) 0.027(17) C41 0.086(18) 0.052(15) 0.12(2) -0.020(17) 0.011(19) 0.006(14) C42 0.09(2) 0.075(18) 0.12(2) 0.028(19) 0.04(2) 0.021(16) C43 0.09(2) 0.070(18) 0.09(2) 0.043(17) 0.008(19) 0.046(16) C44 0.088(19) 0.067(16) 0.15(3) -0.03(2) -0.08(2) -0.015(15) C46 0.14(3) 0.049(16) 0.17(3) -0.01(2) -0.04(3) -0.001(18) C48 0.12(2) 0.090(19) 0.14(3) -0.02(2) 0.01(2) 0.001(18) O3 0.10(2) 0.19(3) 0.08(2) -0.08(2) -0.028(17) 0.061(19) N3 0.072(14) 0.051(12) 0.080(17) -0.044(14) 0.028(16) 0.016(11) C61 0.075(16) 0.101(18) 0.16(2) 0.019(19) 0.06(2) 0.010(16) C62 0.077(18) 0.094(19) 0.13(3) 0.01(2) 0.06(2) 0.022(17) C63 0.078(18) 0.10(2) 0.18(3) 0.01(2) 0.04(2) 0.051(18) C64 0.085(19) 0.11(2) 0.22(3) 0.02(3) 0.03(3) 0.031(19) C65 0.075(17) 0.074(16) 0.19(2) 0.01(2) 0.03(2) 0.001(15) C66 0.075(16) 0.070(15) 0.14(2) -0.020(18) 0.03(2) 0.010(15) C67 0.10(2) 0.064(16) 0.09(2) -0.034(17) 0.03(2) -0.029(15) C68 0.085(18) 0.051(15) 0.08(2) -0.050(16) 0.023(17) -0.003(14) C69 0.041(15) 0.033(13) 0.14(2) -0.009(16) -0.026(17) -0.015(13) C70 0.07(2) 0.048(16) 0.14(3) -0.010(17) -0.027(19) 0.002(15) C71 0.078(17) 0.043(13) 0.11(2) -0.031(17) -0.002(19) 0.017(13) C72 0.11(2) 0.041(15) 0.11(2) -0.005(17) 0.01(2) 0.004(15) C73 0.11(2) 0.040(16) 0.09(2) 0.001(15) 0.01(2) 0.006(15) C74 0.070(18) 0.13(2) 0.16(3) 0.03(2) 0.09(2) -0.007(19) C76 0.074(19) 0.10(2) 0.21(3) 0.00(3) 0.04(3) -0.012(18) C78 0.081(18) 0.060(14) 0.09(2) 0.011(17) 0.00(2) 0.022(14) _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 O1 C7 1.19(2) . ? N1 C6 1.3988 . ? N1 C7 1.48(2) . ? C1 C2 1.3899 . ? C1 C6 1.3901 . ? C1 C14 1.49(2) . ? C2 C3 1.3900 . ? C3 C4 1.3899 . ? C4 C5 1.3899 . ? C5 C6 1.3899 . ? C5 C16 1.47(2) . ? C7 C8 1.5572 . ? C8 C9 1.3899 . ? C8 C13 1.3900 . ? C9 C10 1.3900 . ? C10 C11 1.3900 . ? C11 C12 1.3899 . ? C11 C18 1.49(2) . ? C12 C13 1.3900 . ? C14 C15 1.48(3) . ? C16 C17 1.49(2) . ? C18 C21 1.50(3) . ? C18 C19 1.51(3) . ? C18 C20 1.52(3) . ? O2 C37 1.50(3) . ? N2 C37 1.36(2) . ? N2 C36 1.4607 . ? C31 C32 1.3899 . ? C31 C36 1.3901 . ? C31 C44 1.53(2) . ? C32 C33 1.3899 . ? C33 C34 1.3901 . ? C34 C35 1.3898 . ? C35 C36 1.3901 . ? C35 C46 1.49(2) . ? C37 C38 1.5244 . ? C38 C39 1.3899 . ? C38 C43 1.3900 . ? C39 C40 1.3902 . ? C40 C41 1.3898 . ? C41 C42 1.3899 . ? C41 C48 1.51(2) . ? C42 C43 1.3902 . ? C44 C45 1.51(3) . ? C46 C47 1.47(3) . ? C48 C51 1.51(3) . ? C48 C50 1.51(3) . ? C48 C49 1.52(3) . ? O3 C67 1.35(3) . ? N3 C67 1.37(2) . ? N3 C66 1.4319 . ? C61 C62 1.3900 . ? C61 C66 1.3901 . ? C61 C74 1.49(2) . ? C62 C63 1.3900 . ? C63 C64 1.3901 . ? C64 C65 1.3901 . ? C65 C66 1.3898 . ? C65 C76 1.48(2) . ? C67 C68 1.5676 . ? C68 C69 1.3900 . ? C68 C73 1.3900 . ? C69 C70 1.3898 . ? C70 C71 1.3900 . ? C71 C72 1.3900 . ? C71 C78 1.49(2) . ? C72 C73 1.3901 . ? C74 C75 1.51(3) . ? C76 C77 1.46(3) . ? C78 C80 1.49(2) . ? C78 C79 1.51(3) . ? C78 C81 1.52(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 C6 N1 C7 114.6(7) . . ? C2 C1 C6 120.0 . . ? C2 C1 C14 119.8(15) . . ? C6 C1 C14 120.2(15) . . ? C1 C2 C3 120.0 . . ? C4 C3 C2 120.0 . . ? C3 C4 C5 120.0 . . ? C6 C5 C4 120.0 . . ? C6 C5 C16 122.3(10) . . ? C4 C5 C16 117.7(10) . . ? C5 C6 C1 120.0 . . ? C5 C6 N1 119.8 . . ? C1 C6 N1 119.9 . . ? O1 C7 N1 130.1(16) . . ? O1 C7 C8 123.7(13) . . ? N1 C7 C8 106.2(7) . . ? C9 C8 C13 120.0 . . ? C9 C8 C7 125.3 . . ? C13 C8 C7 114.7 . . ? C8 C9 C10 120.0 . . ? C11 C10 C9 120.0 . . ? C12 C11 C10 120.0 . . ? C12 C11 C18 120.7(17) . . ? C10 C11 C18 119.3(17) . . ? C11 C12 C13 120.0 . . ? C12 C13 C8 120.0 . . ? C15 C14 C1 112(4) . . ? C5 C16 C17 107.9(18) . . ? C11 C18 C21 114(3) . . ? C11 C18 C19 104(3) . . ? C21 C18 C19 104(4) . . ? C11 C18 C20 111(3) . . ? C21 C18 C20 109(3) . . ? C19 C18 C20 114(4) . . ? C37 N2 C36 115.1(8) . . ? C32 C31 C36 120.0 . . ? C32 C31 C44 121.1(14) . . ? C36 C31 C44 118.9(13) . . ? C33 C32 C31 120.0 . . ? C32 C33 C34 120.0 . . ? C35 C34 C33 120.0 . . ? C34 C35 C36 120.0 . . ? C34 C35 C46 115.8(15) . . ? C36 C35 C46 124.2(15) . . ? C35 C36 C31 120.0 . . ? C35 C36 N2 122.0 . . ? C31 C36 N2 117.6 . . ? N2 C37 O2 130.6(14) . . ? N2 C37 C38 110.2(8) . . ? O2 C37 C38 119.2(11) . . ? C39 C38 C43 120.0 . . ? C39 C38 C37 123.8 . . ? C43 C38 C37 116.2 . . ? C38 C39 C40 120.0 . . ? C41 C40 C39 120.0 . . ? C40 C41 C42 120.0 . . ? C40 C41 C48 121.7(15) . . ? C42 C41 C48 118.3(15) . . ? C41 C42 C43 120.0 . . ? C38 C43 C42 120.0 . . ? C45 C44 C31 110.2(19) . . ? C47 C46 C35 118(2) . . ? C51 C48 C41 119(3) . . ? C51 C48 C50 113(3) . . ? C41 C48 C50 103(2) . . ? C51 C48 C49 116(4) . . ? C41 C48 C49 104(3) . . ? C50 C48 C49 99(4) . . ? C67 N3 C66 109.9(9) . . ? C62 C61 C66 120.0 . . ? C62 C61 C74 118.9(17) . . ? C66 C61 C74 121.1(17) . . ? C63 C62 C61 120.0 . . ? C62 C63 C64 120.0 . . ? C65 C64 C63 120.0 . . ? C66 C65 C64 120.0 . . ? C66 C65 C76 123.3(15) . . ? C64 C65 C76 116.7(15) . . ? C65 C66 C61 120.0 . . ? C65 C66 N3 119.0 . . ? C61 C66 N3 120.0 . . ? O3 C67 N3 137.7(17) . . ? O3 C67 C68 115.7(13) . . ? N3 C67 C68 106.7(9) . . ? C69 C68 C73 120.0 . . ? C69 C68 C67 124.2 . . ? C73 C68 C67 115.7 . . ? C70 C69 C68 120.0 . . ? C69 C70 C71 120.0 . . ? C72 C71 C70 120.0 . . ? C72 C71 C78 120.1(16) . . ? C70 C71 C78 119.9(16) . . ? C71 C72 C73 120.0 . . ? C68 C73 C72 120.0 . . ? C61 C74 C75 110(3) . . ? C77 C76 C65 113(3) . . ? C80 C78 C71 115(2) . . ? C80 C78 C79 99(3) . . ? C71 C78 C79 116(2) . . ? C80 C78 C81 117(3) . . ? C71 C78 C81 110(3) . . ? C79 C78 C81 100(3) . . ? _diffrn_measured_fraction_theta_max 0.731 _diffrn_reflns_theta_full 19.33 _diffrn_measured_fraction_theta_full 0.731 _refine_diff_density_max 0.410 _refine_diff_density_min -0.338 _refine_diff_density_rms 0.100 data_gah06 _database_code_CSD 158577 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H10 N2 O3' _chemical_formula_weight 242.23 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 5.218(2) _cell_length_b 8.412(3) _cell_length_c 13.249(6) _cell_angle_alpha 102.61(4) _cell_angle_beta 98.64(5) _cell_angle_gamma 92.87(3) _cell_volume 559.0(4) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description blocks _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.43 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.439 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 252 _exptl_absorpt_coefficient_mu 0.105 _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 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 2075 _diffrn_reflns_av_R_equivalents 0.0917 _diffrn_reflns_av_sigmaI/netI 0.0627 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.60 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1611 _reflns_number_gt 1226 _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^)+(0.1253P)^2^+0.1381P] 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 0.07(2) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 1611 _refine_ls_number_parameters 164 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0838 _refine_ls_R_factor_gt 0.0664 _refine_ls_wR_factor_ref 0.2196 _refine_ls_wR_factor_gt 0.1922 _refine_ls_goodness_of_fit_ref 1.121 _refine_ls_restrained_S_all 1.121 _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 O1 O 0.3829(4) 0.2201(3) 0.49448(17) 0.0545(7) Uani 1 1 d . . . O2 O 0.4490(6) -0.2762(4) 0.0116(2) 0.0836(9) Uani 1 1 d . . . O3 O 0.7624(6) -0.1149(4) -0.0032(2) 0.0812(9) Uani 1 1 d . . . N1 N 0.8206(5) 0.2786(3) 0.52374(19) 0.0451(7) Uani 1 1 d . . . H1A H 0.9586 0.2661 0.4956 0.054 Uiso 1 1 calc R . . N2 N 0.6058(6) -0.1583(4) 0.0462(2) 0.0552(8) Uani 1 1 d . . . C1 C 0.8532(6) 0.3699(4) 0.6295(2) 0.0400(7) Uani 1 1 d . . . C2 C 1.0703(6) 0.3503(4) 0.6981(2) 0.0458(8) Uani 1 1 d . . . H2A H 1.1896 0.2782 0.6749 0.055 Uiso 1 1 calc R . . C3 C 1.1099(6) 0.4371(4) 0.8005(3) 0.0514(9) Uani 1 1 d . . . H3A H 1.2572 0.4242 0.8461 0.062 Uiso 1 1 calc R . . C4 C 0.9314(6) 0.5444(4) 0.8369(3) 0.0500(9) Uani 1 1 d . . . H4A H 0.9557 0.6010 0.9067 0.060 Uiso 1 1 calc R . . C5 C 0.7189(7) 0.5649(4) 0.7674(3) 0.0514(9) Uani 1 1 d . . . H5A H 0.6009 0.6381 0.7906 0.062 Uiso 1 1 calc R . . C6 C 0.6765(6) 0.4795(4) 0.6641(2) 0.0463(8) Uani 1 1 d . . . H6A H 0.5317 0.4949 0.6181 0.056 Uiso 1 1 calc R . . C7 C 0.5929(6) 0.2095(4) 0.4633(2) 0.0411(8) Uani 1 1 d . . . C8 C 0.6064(5) 0.1148(3) 0.3542(2) 0.0387(7) Uani 1 1 d . . . C9 C 0.7935(6) 0.1536(4) 0.2963(2) 0.0466(8) Uani 1 1 d . . . H9A H 0.9193 0.2400 0.3262 0.056 Uiso 1 1 calc R . . C10 C 0.7946(6) 0.0662(4) 0.1960(2) 0.0479(9) Uani 1 1 d . . . H10A H 0.9189 0.0925 0.1574 0.057 Uiso 1 1 calc R . . C11 C 0.6058(6) -0.0620(4) 0.1538(2) 0.0429(8) Uani 1 1 d . . . C12 C 0.4175(6) -0.1047(4) 0.2085(3) 0.0480(8) Uani 1 1 d . . . H12A H 0.2936 -0.1923 0.1787 0.058 Uiso 1 1 calc R . . C13 C 0.4190(6) -0.0135(4) 0.3085(2) 0.0460(8) Uani 1 1 d . . . H13A H 0.2917 -0.0386 0.3460 0.055 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 O1 0.0356(13) 0.0744(16) 0.0522(14) 0.0071(12) 0.0144(10) 0.0042(11) O2 0.090(2) 0.080(2) 0.0621(18) -0.0147(15) 0.0051(15) -0.0163(17) O3 0.097(2) 0.087(2) 0.0584(17) -0.0023(14) 0.0394(16) -0.0015(16) N1 0.0321(13) 0.0573(16) 0.0454(15) 0.0060(12) 0.0133(11) 0.0046(11) N2 0.0602(19) 0.0555(18) 0.0493(17) 0.0085(14) 0.0097(15) 0.0140(15) C1 0.0385(16) 0.0419(16) 0.0390(16) 0.0060(13) 0.0105(13) -0.0010(12) C2 0.0370(16) 0.0503(18) 0.0498(19) 0.0079(15) 0.0099(14) 0.0065(13) C3 0.0483(19) 0.056(2) 0.0498(19) 0.0123(16) 0.0083(15) 0.0053(15) C4 0.0536(19) 0.0480(18) 0.0463(18) 0.0033(15) 0.0144(15) 0.0001(15) C5 0.0480(19) 0.0456(18) 0.062(2) 0.0066(15) 0.0208(16) 0.0095(14) C6 0.0397(17) 0.0445(17) 0.055(2) 0.0109(15) 0.0092(14) 0.0072(14) C7 0.0348(16) 0.0478(17) 0.0430(17) 0.0133(14) 0.0093(13) 0.0043(13) C8 0.0334(15) 0.0415(16) 0.0433(16) 0.0114(13) 0.0088(12) 0.0067(12) C9 0.0440(17) 0.0470(17) 0.0496(19) 0.0086(15) 0.0159(14) -0.0006(14) C10 0.0436(18) 0.057(2) 0.0482(19) 0.0159(16) 0.0179(14) 0.0065(15) C11 0.0438(17) 0.0446(17) 0.0400(17) 0.0081(14) 0.0068(13) 0.0078(14) C12 0.0423(18) 0.0462(18) 0.0536(19) 0.0090(15) 0.0070(14) 0.0008(14) C13 0.0388(17) 0.0513(18) 0.0515(19) 0.0159(15) 0.0134(14) 0.0033(14) _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 O1 C7 1.228(4) . ? O2 N2 1.213(4) . ? O3 N2 1.210(4) . ? N1 C7 1.354(4) . ? N1 C1 1.424(4) . ? N2 C11 1.478(4) . ? C1 C2 1.382(4) . ? C1 C6 1.392(4) . ? C2 C3 1.373(4) . ? C3 C4 1.394(4) . ? C4 C5 1.374(5) . ? C5 C6 1.379(5) . ? C7 C8 1.504(4) . ? C8 C13 1.385(4) . ? C8 C9 1.397(4) . ? C9 C10 1.373(4) . ? C10 C11 1.382(5) . ? C11 C12 1.383(4) . ? C12 C13 1.377(4) . ? 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 C7 N1 C1 126.1(2) . . ? O3 N2 O2 123.3(3) . . ? O3 N2 C11 118.2(3) . . ? O2 N2 C11 118.6(3) . . ? C2 C1 C6 119.9(3) . . ? C2 C1 N1 118.3(2) . . ? C6 C1 N1 121.8(3) . . ? C3 C2 C1 120.1(3) . . ? C2 C3 C4 120.7(3) . . ? C5 C4 C3 118.6(3) . . ? C4 C5 C6 121.5(3) . . ? C5 C6 C1 119.1(3) . . ? O1 C7 N1 122.9(3) . . ? O1 C7 C8 120.3(3) . . ? N1 C7 C8 116.8(2) . . ? C13 C8 C9 118.9(3) . . ? C13 C8 C7 118.1(3) . . ? C9 C8 C7 123.0(3) . . ? C10 C9 C8 121.0(3) . . ? C9 C10 C11 118.1(3) . . ? C10 C11 C12 122.6(3) . . ? C10 C11 N2 118.8(3) . . ? C12 C11 N2 118.6(3) . . ? C13 C12 C11 117.9(3) . . ? C12 C13 C8 121.3(3) . . ? 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 C7 N1 C1 C2 141.9(3) . . . . ? C7 N1 C1 C6 -39.6(4) . . . . ? C6 C1 C2 C3 0.9(4) . . . . ? N1 C1 C2 C3 179.5(3) . . . . ? C1 C2 C3 C4 0.7(5) . . . . ? C2 C3 C4 C5 -1.8(5) . . . . ? C3 C4 C5 C6 1.4(5) . . . . ? C4 C5 C6 C1 0.0(5) . . . . ? C2 C1 C6 C5 -1.2(4) . . . . ? N1 C1 C6 C5 -179.8(3) . . . . ? C1 N1 C7 O1 0.6(5) . . . . ? C1 N1 C7 C8 -178.5(2) . . . . ? O1 C7 C8 C13 -28.1(4) . . . . ? N1 C7 C8 C13 151.0(3) . . . . ? O1 C7 C8 C9 149.8(3) . . . . ? N1 C7 C8 C9 -31.0(4) . . . . ? C13 C8 C9 C10 -0.4(4) . . . . ? C7 C8 C9 C10 -178.4(3) . . . . ? C8 C9 C10 C11 -0.3(4) . . . . ? C9 C10 C11 C12 0.1(4) . . . . ? C9 C10 C11 N2 -179.4(3) . . . . ? O3 N2 C11 C10 -4.3(4) . . . . ? O2 N2 C11 C10 175.9(3) . . . . ? O3 N2 C11 C12 176.1(3) . . . . ? O2 N2 C11 C12 -3.6(4) . . . . ? C10 C11 C12 C13 0.7(4) . . . . ? N2 C11 C12 C13 -179.7(2) . . . . ? C11 C12 C13 C8 -1.4(4) . . . . ? C9 C8 C13 C12 1.3(4) . . . . ? C7 C8 C13 C12 179.4(2) . . . . ? _diffrn_measured_fraction_theta_max 0.822 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.822 _refine_diff_density_max 0.274 _refine_diff_density_min -0.276 _refine_diff_density_rms 0.069 data_gah08 _database_code_CSD 158578 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C15 H14 N2 O3' _chemical_formula_weight 270.28 _chemical_melting_point ? _chemical_compound_source ? 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 P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 5.639(2) _cell_length_b 9.699(5) _cell_length_c 25.036(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1369.3(10) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description oblongs _exptl_crystal_colour colourless _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.311 _exptl_crystal_density_method ? _exptl_crystal_F_000 568 _exptl_absorpt_coefficient_mu 0.093 _exptl_absorpt_correction_type None _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _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 ? _diffrn_measurement_method ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3570 _diffrn_reflns_av_R_equivalents 0.0388 _diffrn_reflns_av_sigmaI/netI 0.0334 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.25 _diffrn_reflns_theta_max 20.00 _reflns_number_total 1285 _reflns_number_observed 1242 _reflns_observed_criterion >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0961P)^2^+0.4343P] 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 ? _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 -2.60(312) _refine_ls_number_reflns 1285 _refine_ls_number_parameters 181 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0567 _refine_ls_R_factor_obs 0.0555 _refine_ls_wR_factor_all 0.1372 _refine_ls_wR_factor_obs 0.1355 _refine_ls_goodness_of_fit_all 1.087 _refine_ls_goodness_of_fit_obs 1.094 _refine_ls_restrained_S_all 1.087 _refine_ls_restrained_S_obs 1.094 _refine_ls_shift/esd_max 0.004 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group N1 N 0.0523(10) 0.3896(5) 0.9791(2) 0.0798(13) Uani 1 d . . N2 N -0.0245(5) 0.3381(3) 0.72196(11) 0.0407(8) Uani 1 d . . H2B H -0.0595(5) 0.4230(3) 0.73412(11) 0.080 Uiso 1 d R . C1 C 0.0468(8) 0.3533(5) 0.9217(2) 0.0569(12) Uani 1 d . . C2 C -0.1143(10) 0.4136(4) 0.8894(2) 0.0626(13) Uani 1 d . . H2A H -0.2318(10) 0.4725(4) 0.9052(2) 0.080 Uiso 1 d R . C3 C -0.1237(8) 0.3796(4) 0.8355(2) 0.0542(11) Uani 1 d . . H3A H -0.2350(8) 0.4226(4) 0.8118(2) 0.080 Uiso 1 d R . C4 C 0.0384(7) 0.2862(4) 0.81527(14) 0.0394(10) Uani 1 d . . C5 C 0.2005(8) 0.2265(4) 0.8495(2) 0.0588(12) Uani 1 d . . H5A H 0.3125(8) 0.1613(4) 0.8355(2) 0.080 Uiso 1 d R . C6 C 0.2072(9) 0.2608(5) 0.9026(2) 0.0715(14) Uani 1 d . . H6A H 0.3064(9) 0.2134(5) 0.9278(2) 0.080 Uiso 1 d R . C7 C 0.0352(6) 0.2423(4) 0.75803(14) 0.0382(10) Uani 1 d . . C8 C -0.0459(6) 0.3120(4) 0.66572(14) 0.0379(10) Uani 1 d . . C9 C -0.2229(7) 0.2245(4) 0.6475(2) 0.0480(10) Uani 1 d . . C10 C -0.2451(9) 0.2081(5) 0.5918(2) 0.0655(13) Uani 1 d . . H13A H -0.3693(9) 0.1500(5) 0.5784(2) 0.080 Uiso 1 d R . C11 C -0.0975(10) 0.2758(5) 0.5575(2) 0.0722(14) Uani 1 d . . H12A H -0.1104(10) 0.2604(5) 0.5197(2) 0.080 Uiso 1 d R . C12 C 0.0740(9) 0.3592(5) 0.5768(2) 0.0626(12) Uani 1 d . . H11A H 0.1777(9) 0.4054(5) 0.5522(2) 0.080 Uiso 1 d R . C13 C 0.1071(7) 0.3797(4) 0.6311(2) 0.0464(11) Uani 1 d . . C14 C -0.3917(8) 0.1527(5) 0.6838(2) 0.0660(12) Uani 1 d . . H14A H -0.4995(8) 0.0973(5) 0.6633(2) 0.080 Uiso 1 d R . H14B H -0.3043(8) 0.0947(5) 0.7078(2) 0.080 Uiso 1 d R . H14C H -0.4795(8) 0.2198(5) 0.7039(2) 0.080 Uiso 1 d R . C15 C 0.2998(8) 0.4739(4) 0.6505(2) 0.0618(12) Uani 1 d . . H15A H 0.2990(8) 0.4772(4) 0.6888(2) 0.080 Uiso 1 d R . H15B H 0.4491(8) 0.4383(4) 0.6383(2) 0.080 Uiso 1 d R . H15C H 0.2769(8) 0.5652(4) 0.6365(2) 0.080 Uiso 1 d R . O1 O 0.2044(9) 0.3399(5) 1.0073(2) 0.118(2) Uani 1 d . . O2 O -0.0960(10) 0.4675(4) 0.99561(13) 0.1083(15) Uani 1 d . . O3 O 0.0858(4) 0.1233(3) 0.74592(9) 0.0487(8) Uani 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 N1 0.122(4) 0.068(3) 0.049(3) -0.006(2) 0.006(3) 0.000(3) N2 0.050(2) 0.035(2) 0.037(2) 0.0000(15) 0.0046(14) 0.005(2) C1 0.083(3) 0.053(2) 0.035(2) -0.008(2) 0.003(2) -0.001(3) C2 0.083(3) 0.056(3) 0.048(3) 0.002(2) 0.015(3) 0.019(3) C3 0.062(3) 0.053(2) 0.047(3) 0.006(2) 0.008(2) 0.016(2) C4 0.043(2) 0.036(2) 0.039(2) 0.002(2) 0.005(2) -0.001(2) C5 0.060(3) 0.068(3) 0.049(3) -0.006(2) -0.001(2) 0.019(3) C6 0.078(3) 0.088(3) 0.049(3) 0.001(3) -0.014(2) 0.017(3) C7 0.036(2) 0.037(2) 0.042(2) 0.000(2) 0.008(2) -0.005(2) C8 0.035(2) 0.038(2) 0.041(2) 0.004(2) 0.007(2) 0.003(2) C9 0.044(2) 0.049(2) 0.051(3) -0.001(2) -0.001(2) 0.001(2) C10 0.065(3) 0.064(3) 0.068(3) -0.004(2) -0.018(3) -0.001(3) C11 0.086(3) 0.084(3) 0.047(3) -0.006(3) -0.003(3) -0.003(3) C12 0.075(3) 0.065(3) 0.048(3) 0.009(2) 0.017(2) -0.004(3) C13 0.050(2) 0.042(2) 0.048(3) 0.000(2) 0.003(2) 0.004(2) C14 0.047(2) 0.072(3) 0.080(3) 0.008(2) -0.002(2) -0.013(3) C15 0.055(3) 0.056(2) 0.074(3) -0.001(2) 0.017(2) -0.008(2) O1 0.144(4) 0.145(4) 0.064(2) -0.024(2) -0.032(3) 0.031(4) O2 0.172(4) 0.092(3) 0.061(2) -0.010(2) 0.020(3) 0.029(3) O3 0.061(2) 0.038(2) 0.047(2) -0.0024(13) 0.0084(14) 0.0037(14) _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 N1 O2 1.201(6) . ? N1 O1 1.212(5) . ? N1 C1 1.479(6) . ? N2 C7 1.339(5) . ? N2 C8 1.435(5) . ? C1 C2 1.350(6) . ? C1 C6 1.361(6) . ? C2 C3 1.390(6) . ? C3 C4 1.383(5) . ? C4 C5 1.380(5) . ? C4 C7 1.495(5) . ? C5 C6 1.372(6) . ? C7 O3 1.227(4) . ? C8 C13 1.388(5) . ? C8 C9 1.388(5) . ? C9 C10 1.408(6) . ? C9 C14 1.489(6) . ? C10 C11 1.365(6) . ? C11 C12 1.351(7) . ? C12 C13 1.387(6) . ? C13 C15 1.500(6) . ? 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 O2 N1 O1 122.8(4) . . ? O2 N1 C1 118.0(5) . . ? O1 N1 C1 119.1(5) . . ? C7 N2 C8 124.1(3) . . ? C2 C1 C6 121.5(4) . . ? C2 C1 N1 119.5(4) . . ? C6 C1 N1 119.0(4) . . ? C1 C2 C3 120.3(4) . . ? C4 C3 C2 119.1(4) . . ? C5 C4 C3 119.0(3) . . ? C5 C4 C7 118.9(3) . . ? C3 C4 C7 122.0(3) . . ? C6 C5 C4 121.2(4) . . ? C1 C6 C5 118.8(4) . . ? O3 C7 N2 123.0(3) . . ? O3 C7 C4 120.1(3) . . ? N2 C7 C4 116.9(3) . . ? C13 C8 C9 122.1(3) . . ? C13 C8 N2 118.5(3) . . ? C9 C8 N2 119.4(3) . . ? C8 C9 C10 117.3(4) . . ? C8 C9 C14 123.1(4) . . ? C10 C9 C14 119.6(4) . . ? C11 C10 C9 121.0(4) . . ? C12 C11 C10 119.9(4) . . ? C11 C12 C13 122.2(4) . . ? C12 C13 C8 117.4(4) . . ? C12 C13 C15 120.1(4) . . ? C8 C13 C15 122.5(3) . . ? 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 O2 N1 C1 C2 3.6(7) . . . . ? O1 N1 C1 C2 -176.6(4) . . . . ? O2 N1 C1 C6 -177.3(4) . . . . ? O1 N1 C1 C6 2.5(7) . . . . ? C6 C1 C2 C3 1.6(7) . . . . ? N1 C1 C2 C3 -179.3(4) . . . . ? C1 C2 C3 C4 -1.8(6) . . . . ? C2 C3 C4 C5 1.8(6) . . . . ? C2 C3 C4 C7 178.5(4) . . . . ? C3 C4 C5 C6 -1.6(6) . . . . ? C7 C4 C5 C6 -178.5(4) . . . . ? C2 C1 C6 C5 -1.4(7) . . . . ? N1 C1 C6 C5 179.5(4) . . . . ? C4 C5 C6 C1 1.4(7) . . . . ? C8 N2 C7 O3 2.7(5) . . . . ? C8 N2 C7 C4 -177.3(3) . . . . ? C5 C4 C7 O3 32.6(5) . . . . ? C3 C4 C7 O3 -144.1(4) . . . . ? C5 C4 C7 N2 -147.4(4) . . . . ? C3 C4 C7 N2 35.8(5) . . . . ? C7 N2 C8 C13 -116.6(4) . . . . ? C7 N2 C8 C9 65.7(4) . . . . ? C13 C8 C9 C10 -1.0(5) . . . . ? N2 C8 C9 C10 176.6(3) . . . . ? C13 C8 C9 C14 -178.9(4) . . . . ? N2 C8 C9 C14 -1.3(5) . . . . ? C8 C9 C10 C11 0.1(6) . . . . ? C14 C9 C10 C11 178.1(4) . . . . ? C9 C10 C11 C12 0.5(7) . . . . ? C10 C11 C12 C13 -0.1(7) . . . . ? C11 C12 C13 C8 -0.8(6) . . . . ? C11 C12 C13 C15 -179.8(4) . . . . ? C9 C8 C13 C12 1.4(5) . . . . ? N2 C8 C13 C12 -176.3(4) . . . . ? C9 C8 C13 C15 -179.7(3) . . . . ? N2 C8 C13 C15 2.7(5) . . . . ? _refine_diff_density_max 0.245 _refine_diff_density_min -0.296 _refine_diff_density_rms 0.099 data_gah09 _database_code_CSD 158579 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C17 H18 N2 O3' _chemical_formula_weight 298.33 _chemical_melting_point ? _chemical_compound_source ? 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 Cc 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' _cell_length_a 8.916(5) _cell_length_b 23.665(7) _cell_length_c 7.924(3) _cell_angle_alpha 90.00 _cell_angle_beta 107.02(3) _cell_angle_gamma 90.00 _cell_volume 1598.7(11) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 42 _cell_measurement_theta_min 10 _cell_measurement_theta_max 12.5 _exptl_crystal_description prismatic _exptl_crystal_colour colourless _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.239 _exptl_crystal_density_method ? _exptl_crystal_F_000 632 _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _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 'Siemens P4' _diffrn_measurement_method omega _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time 60 _diffrn_standards_decay_% 0 _diffrn_reflns_number 1031 _diffrn_reflns_av_R_equivalents 0.0152 _diffrn_reflns_av_sigmaI/netI 0.0325 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -1 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 2.54 _diffrn_reflns_theta_max 20.00 _reflns_number_total 932 _reflns_number_observed 801 _reflns_observed_criterion >4sigma(I) _computing_data_collection 'Siemens P4' _computing_cell_refinement 'Siemens XSCANS' _computing_data_reduction 'Siemens XPREP' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics SHELXTL-PLUS _computing_publication_material SHELXT-93 _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0658P)^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 ? _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 0.79(303) _refine_ls_number_reflns 932 _refine_ls_number_parameters 199 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0451 _refine_ls_R_factor_obs 0.0375 _refine_ls_wR_factor_all 0.0983 _refine_ls_wR_factor_obs 0.0937 _refine_ls_goodness_of_fit_all 1.010 _refine_ls_goodness_of_fit_obs 1.061 _refine_ls_restrained_S_all 1.009 _refine_ls_restrained_S_obs 1.060 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group N1 N -0.0267(7) 0.5034(2) -0.0356(9) 0.084(2) Uani 1 d . . N2 N -0.0219(5) 0.2292(2) 0.0062(5) 0.0559(12) Uani 1 d . . H2A H -0.1000(5) 0.2414(2) -0.0867(5) 0.080 Uiso 1 d R . O1 O -0.1320(6) 0.5180(2) -0.1668(7) 0.105(2) Uani 1 d . . O2 O 0.0541(7) 0.5364(2) 0.0661(7) 0.130(2) Uani 1 d . . O3 O 0.1979(5) 0.2524(2) 0.2121(5) 0.0829(13) Uani 1 d . . C1 C 0.0010(7) 0.4418(2) -0.0051(8) 0.061(2) Uani 1 d . . C2 C -0.1010(7) 0.4056(2) -0.1069(8) 0.070(2) Uani 1 d . . H2B H -0.1885(7) 0.4192(2) -0.2003(8) 0.080 Uiso 1 d R . C3 C -0.0778(8) 0.3478(2) -0.0754(7) 0.069(2) Uani 1 d . . H3A H -0.1530(8) 0.3215(2) -0.1442(7) 0.080 Uiso 1 d R . C4 C 0.0480(6) 0.3282(2) 0.0533(6) 0.0504(14) Uani 1 d . . C5 C 0.1507(7) 0.3679(2) 0.1539(8) 0.070(2) Uani 1 d . . H5A H 0.2418(7) 0.3550(2) 0.2439(8) 0.080 Uiso 1 d R . C6 C 0.1286(8) 0.4248(2) 0.1268(8) 0.074(2) Uani 1 d . . H6A H 0.1983(8) 0.4520(2) 0.1997(8) 0.080 Uiso 1 d R . C7 C 0.0830(7) 0.2668(2) 0.0991(7) 0.0515(14) Uani 1 d . . C8 C -0.0143(7) 0.1695(2) 0.0431(6) 0.0532(15) Uani 1 d . . C9 C -0.0995(8) 0.1475(2) 0.1488(7) 0.065(2) Uani 1 d . . C10 C -0.0954(9) 0.0901(3) 0.1767(9) 0.087(2) Uani 1 d . . H10A H -0.1517(9) 0.0744(3) 0.2519(9) 0.080 Uiso 1 d R . C11 C -0.0113(10) 0.0554(3) 0.0986(11) 0.094(2) Uani 1 d . . H11A H -0.0133(10) 0.0153(3) 0.1151(11) 0.080 Uiso 1 d R . C12 C 0.0713(8) 0.0770(3) -0.0023(9) 0.084(2) Uani 1 d . . H12A H 0.1295(8) 0.0520(3) -0.0552(9) 0.080 Uiso 1 d R . C13 C 0.0745(7) 0.1353(2) -0.0333(8) 0.064(2) Uani 1 d . . C14 C 0.1704(9) 0.1585(3) -0.1457(9) 0.096(2) Uani 1 d . . H14A H 0.2702(9) 0.1398(3) -0.1175(9) 0.080 Uiso 1 d R . H14B H 0.1889(9) 0.1981(3) -0.1212(9) 0.080 Uiso 1 d R . C15 C 0.1009(13) 0.1506(4) -0.3306(12) 0.154(4) Uani 1 d . . H15A H 0.1629(13) 0.1658(4) -0.4005(12) 0.080 Uiso 1 d R . H15B H 0.0838(13) 0.1110(4) -0.3552(12) 0.080 Uiso 1 d R . H15C H 0.0018(13) 0.1698(4) -0.3590(12) 0.080 Uiso 1 d R . C16 C -0.2022(9) 0.1842(3) 0.2256(9) 0.089(2) Uani 1 d . . H16A H -0.1559(9) 0.2211(3) 0.2491(9) 0.080 Uiso 1 d R . H16B H -0.2041(9) 0.1680(3) 0.3360(9) 0.080 Uiso 1 d R . C17 C -0.3671(9) 0.1909(3) 0.1083(9) 0.099(2) Uani 1 d . . H17A H -0.4267(9) 0.2143(3) 0.1640(9) 0.080 Uiso 1 d R . H17B H -0.3656(9) 0.2078(3) -0.0014(9) 0.080 Uiso 1 d R . H17C H -0.4143(9) 0.1542(3) 0.0862(9) 0.080 Uiso 1 d 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 N1 0.081(4) 0.057(4) 0.112(4) 0.007(4) 0.026(4) 0.001(4) N2 0.048(3) 0.047(3) 0.058(3) 0.005(2) -0.007(3) 0.004(3) O1 0.110(4) 0.064(3) 0.130(4) 0.010(3) 0.018(4) 0.021(3) O2 0.134(5) 0.049(3) 0.176(5) -0.015(3) 0.000(4) -0.024(3) O3 0.068(3) 0.059(2) 0.087(3) 0.000(2) -0.032(2) 0.010(2) C1 0.062(4) 0.038(3) 0.082(4) 0.001(3) 0.017(4) 0.001(3) C2 0.061(4) 0.050(4) 0.084(4) 0.005(3) -0.005(4) 0.003(4) C3 0.069(4) 0.051(4) 0.067(4) -0.007(3) -0.012(4) -0.003(4) C4 0.039(3) 0.051(3) 0.055(3) -0.001(3) 0.004(3) 0.002(3) C5 0.059(4) 0.063(4) 0.072(4) -0.010(3) -0.006(3) -0.010(3) C6 0.065(4) 0.047(4) 0.095(4) -0.005(3) -0.001(4) -0.003(3) C7 0.050(3) 0.046(4) 0.051(3) -0.002(3) 0.002(3) 0.005(3) C8 0.047(3) 0.054(4) 0.046(3) -0.003(3) -0.005(3) 0.005(4) C9 0.067(4) 0.056(4) 0.062(3) 0.005(3) 0.002(3) -0.009(4) C10 0.082(5) 0.090(6) 0.085(5) 0.015(4) 0.016(4) -0.018(5) C11 0.085(5) 0.055(5) 0.121(6) 0.018(4) -0.002(5) -0.007(4) C12 0.062(5) 0.070(5) 0.106(5) -0.009(4) 0.003(4) 0.011(4) C13 0.051(4) 0.055(4) 0.076(4) 0.000(3) 0.001(3) -0.006(3) C14 0.093(5) 0.087(5) 0.108(6) -0.014(4) 0.033(5) 0.013(4) C15 0.177(9) 0.161(8) 0.151(9) -0.025(7) 0.091(8) -0.050(7) C16 0.102(6) 0.094(5) 0.082(4) 0.004(4) 0.043(4) -0.007(4) C17 0.093(6) 0.094(5) 0.116(5) -0.005(4) 0.037(5) 0.004(4) _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 N1 O2 1.200(6) . ? N1 O1 1.229(6) . ? N1 C1 1.485(7) . ? N2 C7 1.343(6) . ? N2 C8 1.440(7) . ? O3 C7 1.197(6) . ? C1 C2 1.334(7) . ? C1 C6 1.361(8) . ? C2 C3 1.395(7) . ? C3 C4 1.358(7) . ? C4 C5 1.390(7) . ? C4 C7 1.508(7) . ? C5 C6 1.370(8) . ? C8 C9 1.387(8) . ? C8 C13 1.389(8) . ? C9 C10 1.373(8) . ? C9 C16 1.514(9) . ? C10 C11 1.376(11) . ? C11 C12 1.337(10) . ? C12 C13 1.403(8) . ? C13 C14 1.508(9) . ? C14 C15 1.426(10) . ? C16 C17 1.500(9) . ? 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 O2 N1 O1 123.0(5) . . ? O2 N1 C1 119.4(6) . . ? O1 N1 C1 117.6(6) . . ? C7 N2 C8 123.7(4) . . ? C2 C1 C6 122.9(5) . . ? C2 C1 N1 118.6(5) . . ? C6 C1 N1 118.5(5) . . ? C1 C2 C3 118.8(5) . . ? C4 C3 C2 121.1(5) . . ? C3 C4 C5 117.4(5) . . ? C3 C4 C7 125.3(5) . . ? C5 C4 C7 117.3(5) . . ? C6 C5 C4 122.3(5) . . ? C1 C6 C5 117.4(5) . . ? O3 C7 N2 121.9(4) . . ? O3 C7 C4 121.8(5) . . ? N2 C7 C4 116.4(5) . . ? C9 C8 C13 121.8(5) . . ? C9 C8 N2 119.4(5) . . ? C13 C8 N2 118.8(6) . . ? C10 C9 C8 118.3(6) . . ? C10 C9 C16 119.6(7) . . ? C8 C9 C16 121.9(5) . . ? C11 C10 C9 120.7(7) . . ? C12 C11 C10 120.6(6) . . ? C11 C12 C13 121.5(7) . . ? C8 C13 C12 117.0(6) . . ? C8 C13 C14 122.6(5) . . ? C12 C13 C14 120.4(6) . . ? C15 C14 C13 114.0(7) . . ? C17 C16 C9 114.2(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 O2 N1 C1 C2 172.2(6) . . . . ? O1 N1 C1 C2 -8.5(8) . . . . ? O2 N1 C1 C6 -7.1(8) . . . . ? O1 N1 C1 C6 172.2(6) . . . . ? C6 C1 C2 C3 1.1(9) . . . . ? N1 C1 C2 C3 -178.2(6) . . . . ? C1 C2 C3 C4 -1.7(10) . . . . ? C2 C3 C4 C5 1.1(8) . . . . ? C2 C3 C4 C7 179.4(6) . . . . ? C3 C4 C5 C6 -0.1(8) . . . . ? C7 C4 C5 C6 -178.5(6) . . . . ? C2 C1 C6 C5 -0.1(9) . . . . ? N1 C1 C6 C5 179.2(5) . . . . ? C4 C5 C6 C1 -0.5(9) . . . . ? C8 N2 C7 O3 5.8(8) . . . . ? C8 N2 C7 C4 -174.2(5) . . . . ? C3 C4 C7 O3 178.5(5) . . . . ? C5 C4 C7 O3 -3.2(8) . . . . ? C3 C4 C7 N2 -1.5(8) . . . . ? C5 C4 C7 N2 176.8(5) . . . . ? C7 N2 C8 C9 94.9(6) . . . . ? C7 N2 C8 C13 -87.1(6) . . . . ? C13 C8 C9 C10 -0.3(7) . . . . ? N2 C8 C9 C10 177.5(5) . . . . ? C13 C8 C9 C16 -177.2(5) . . . . ? N2 C8 C9 C16 0.7(7) . . . . ? C8 C9 C10 C11 -1.3(9) . . . . ? C16 C9 C10 C11 175.6(6) . . . . ? C9 C10 C11 C12 1.8(11) . . . . ? C10 C11 C12 C13 -0.5(11) . . . . ? C9 C8 C13 C12 1.5(7) . . . . ? N2 C8 C13 C12 -176.4(4) . . . . ? C9 C8 C13 C14 -178.8(5) . . . . ? N2 C8 C13 C14 3.4(7) . . . . ? C11 C12 C13 C8 -1.1(9) . . . . ? C11 C12 C13 C14 179.2(6) . . . . ? C8 C13 C14 C15 -103.0(7) . . . . ? C12 C13 C14 C15 76.7(8) . . . . ? C10 C9 C16 C17 -88.3(7) . . . . ? C8 C9 C16 C17 88.5(7) . . . . ? _refine_diff_density_max 0.093 _refine_diff_density_min -0.131 _refine_diff_density_rms 0.026 data_gah10 _database_code_CSD 158580 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H22 N2 O3' _chemical_formula_weight 326.39 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)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 19.197(3) _cell_length_b 9.7545(15) _cell_length_c 19.767(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.374(3) _cell_angle_gamma 90.00 _cell_volume 3701.4(10) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 300 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description BLOCK _exptl_crystal_colour COLOURLESS _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.171 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1392 _exptl_absorpt_coefficient_mu 0.080 _exptl_absorpt_correction_type semi-empirical _exptl_absorpt_correction_T_min 0.9719 _exptl_absorpt_correction_T_max 0.9905 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 21707 _diffrn_reflns_av_R_equivalents 0.1050 _diffrn_reflns_av_sigmaI/netI 0.1267 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.47 _diffrn_reflns_theta_max 28.31 _reflns_number_total 8792 _reflns_number_gt 3766 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0868P)^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 8792 _refine_ls_number_parameters 433 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1770 _refine_ls_R_factor_gt 0.0731 _refine_ls_wR_factor_ref 0.1953 _refine_ls_wR_factor_gt 0.1560 _refine_ls_goodness_of_fit_ref 0.872 _refine_ls_restrained_S_all 0.872 _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 N1A N 0.23824(12) 0.7438(2) 0.24863(11) 0.0287(5) Uani 1 1 d . . . H1AA H 0.2523 0.8284 0.2414 0.034 Uiso 1 1 calc R . . N2A N 0.50692(13) 0.7532(3) 0.05142(12) 0.0397(6) Uani 1 1 d . . . O1A O 0.25774(12) 0.52146(19) 0.23120(13) 0.0649(8) Uani 1 1 d . . . O2A O 0.52701(13) 0.8710(2) 0.04383(13) 0.0657(7) Uani 1 1 d . . . O3A O 0.53405(13) 0.6558(2) 0.02337(12) 0.0606(7) Uani 1 1 d . . . C1A C 0.27489(15) 0.6418(3) 0.22227(14) 0.0333(7) Uani 1 1 d . . . C2A C 0.33607(14) 0.6771(2) 0.17844(13) 0.0288(6) Uani 1 1 d . . . C3A C 0.37244(16) 0.5691(3) 0.14971(15) 0.0386(7) Uani 1 1 d . . . H3AA H 0.3589 0.4774 0.1592 0.046 Uiso 1 1 calc R . . C4A C 0.42828(15) 0.5934(3) 0.10731(14) 0.0372(7) Uani 1 1 d . . . H4AA H 0.4527 0.5197 0.0869 0.045 Uiso 1 1 calc R . . C5A C 0.44743(15) 0.7277(3) 0.09542(13) 0.0300(6) Uani 1 1 d . . . C6A C 0.41286(16) 0.8358(3) 0.12333(14) 0.0361(7) Uani 1 1 d . . . H6AA H 0.4273 0.9271 0.1142 0.043 Uiso 1 1 calc R . . C7A C 0.35662(15) 0.8115(3) 0.16511(14) 0.0339(7) Uani 1 1 d . . . H7AA H 0.3321 0.8861 0.1846 0.041 Uiso 1 1 calc R . . C8A C 0.17694(14) 0.7232(2) 0.28821(13) 0.0277(6) Uani 1 1 d . . . C9A C 0.11211(16) 0.7247(3) 0.25474(15) 0.0344(7) Uani 1 1 d . . . C10A C 0.05321(17) 0.7152(3) 0.29524(17) 0.0448(8) Uani 1 1 d . . . H10A H 0.0084 0.7168 0.2746 0.054 Uiso 1 1 calc R . . C11A C 0.05838(18) 0.7036(3) 0.36447(17) 0.0445(9) Uani 1 1 d . . . H11A H 0.0173 0.6987 0.3910 0.053 Uiso 1 1 calc R . . C12A C 0.12230(18) 0.6991(3) 0.39526(15) 0.0418(8) Uani 1 1 d . . . H12A H 0.1252 0.6895 0.4430 0.050 Uiso 1 1 calc R . . C13A C 0.18297(15) 0.7083(3) 0.35796(14) 0.0350(7) Uani 1 1 d . . . C14A C 0.25369(19) 0.7076(3) 0.39307(16) 0.0527(9) Uani 1 1 d . . . H14A H 0.2897 0.7021 0.3568 0.063 Uiso 1 1 calc R . . C15A C 0.2663(3) 0.8400(4) 0.4311(3) 0.1038(18) Uani 1 1 d . . . H15A H 0.2599 0.9178 0.4003 0.156 Uiso 1 1 calc R . . H15B H 0.3139 0.8407 0.4492 0.156 Uiso 1 1 calc R . . H15C H 0.2331 0.8472 0.4684 0.156 Uiso 1 1 calc R . . C16A C 0.2637(3) 0.5836(4) 0.4381(3) 0.1039(18) Uani 1 1 d . . . H16A H 0.2558 0.5000 0.4116 0.156 Uiso 1 1 calc R . . H16B H 0.2304 0.5873 0.4754 0.156 Uiso 1 1 calc R . . H16C H 0.3113 0.5832 0.4563 0.156 Uiso 1 1 calc R . . C17A C 0.10559(18) 0.7371(3) 0.17831(16) 0.0487(8) Uani 1 1 d . . . H17A H 0.1537 0.7331 0.1594 0.058 Uiso 1 1 calc R . . C18A C 0.0745(3) 0.8729(4) 0.1576(2) 0.0907(15) Uani 1 1 d . . . H18A H 0.0714 0.8776 0.1081 0.136 Uiso 1 1 calc R . . H18B H 0.1041 0.9475 0.1743 0.136 Uiso 1 1 calc R . . H18C H 0.0278 0.8818 0.1769 0.136 Uiso 1 1 calc R . . C19A C 0.0651(2) 0.6180(4) 0.14845(18) 0.0862(14) Uani 1 1 d . . . H19A H 0.0622 0.6285 0.0992 0.129 Uiso 1 1 calc R . . H19B H 0.0181 0.6166 0.1674 0.129 Uiso 1 1 calc R . . H19C H 0.0890 0.5319 0.1594 0.129 Uiso 1 1 calc R . . N1B N 0.75369(12) 0.2701(2) 0.23238(11) 0.0295(5) Uani 1 1 d . . . H1BA H 0.7539 0.1880 0.2508 0.035 Uiso 1 1 calc R . . N2B N 0.55608(13) 0.2591(3) 0.49800(12) 0.0399(6) Uani 1 1 d . . . O1B O 0.71995(11) 0.49041(17) 0.24180(10) 0.0414(5) Uani 1 1 d . . . O2B O 0.54532(13) 0.1412(2) 0.51460(12) 0.0621(7) Uani 1 1 d . . . O3B O 0.53283(14) 0.3567(2) 0.52858(12) 0.0661(8) Uani 1 1 d . . . C1B C 0.71958(15) 0.3713(3) 0.26380(14) 0.0305(7) Uani 1 1 d . . . C2B C 0.67890(14) 0.3359(2) 0.32610(13) 0.0282(6) Uani 1 1 d . . . C3B C 0.67107(17) 0.2027(3) 0.34998(14) 0.0395(8) Uani 1 1 d . . . H3BA H 0.6932 0.1286 0.3276 0.047 Uiso 1 1 calc R . . C4B C 0.63063(17) 0.1788(3) 0.40682(15) 0.0415(8) Uani 1 1 d . . . H4BA H 0.6253 0.0883 0.4238 0.050 Uiso 1 1 calc R . . C5B C 0.59872(14) 0.2858(3) 0.43791(13) 0.0306(6) Uani 1 1 d . . . C6B C 0.60620(16) 0.4195(3) 0.41548(15) 0.0399(7) Uani 1 1 d . . . H6BA H 0.5843 0.4933 0.4384 0.048 Uiso 1 1 calc R . . C7B C 0.64574(16) 0.4419(3) 0.35976(15) 0.0386(7) Uani 1 1 d . . . H7BA H 0.6508 0.5330 0.3434 0.046 Uiso 1 1 calc R . . C8B C 0.78986(15) 0.2905(2) 0.16991(13) 0.0284(6) Uani 1 1 d . . . C9B C 0.75147(16) 0.2947(3) 0.10946(14) 0.0341(7) Uani 1 1 d . . . C10B C 0.78810(18) 0.3105(3) 0.04960(15) 0.0459(8) Uani 1 1 d . . . H10B H 0.7634 0.3158 0.0079 0.055 Uiso 1 1 calc R . . C11B C 0.85984(19) 0.3186(3) 0.04988(16) 0.0479(9) Uani 1 1 d . . . H11B H 0.8841 0.3284 0.0084 0.057 Uiso 1 1 calc R . . C12B C 0.89624(17) 0.3125(3) 0.10964(17) 0.0431(8) Uani 1 1 d . . . H12B H 0.9456 0.3184 0.1090 0.052 Uiso 1 1 calc R . . C13B C 0.86281(15) 0.2981(3) 0.17074(14) 0.0336(7) Uani 1 1 d . . . C14B C 0.90310(17) 0.2866(3) 0.23685(17) 0.0480(8) Uani 1 1 d . . . H14B H 0.8768 0.2244 0.2677 0.058 Uiso 1 1 calc R . . C15B C 0.9771(2) 0.2245(5) 0.2258(2) 0.0946(16) Uani 1 1 d . . . H15D H 0.9727 0.1345 0.2041 0.142 Uiso 1 1 calc R . . H15E H 1.0008 0.2143 0.2696 0.142 Uiso 1 1 calc R . . H15F H 1.0042 0.2857 0.1968 0.142 Uiso 1 1 calc R . . C16B C 0.9098(2) 0.4250(3) 0.27070(19) 0.0678(11) Uani 1 1 d . . . H16D H 0.8632 0.4627 0.2788 0.102 Uiso 1 1 calc R . . H16E H 0.9358 0.4873 0.2413 0.102 Uiso 1 1 calc R . . H16F H 0.9346 0.4147 0.3139 0.102 Uiso 1 1 calc R . . C17B C 0.67287(17) 0.2787(3) 0.10725(16) 0.0456(8) Uani 1 1 d . . . H17B H 0.6570 0.2650 0.1548 0.055 Uiso 1 1 calc R . . C18B C 0.6373(2) 0.4076(4) 0.0807(2) 0.0791(13) Uani 1 1 d . . . H18D H 0.6522 0.4867 0.1078 0.119 Uiso 1 1 calc R . . H18E H 0.5867 0.3970 0.0839 0.119 Uiso 1 1 calc R . . H18F H 0.6502 0.4222 0.0334 0.119 Uiso 1 1 calc R . . C19B C 0.65136(19) 0.1520(4) 0.06720(19) 0.0652(11) Uani 1 1 d . . . H19D H 0.6749 0.0712 0.0859 0.098 Uiso 1 1 calc R . . H19E H 0.6645 0.1636 0.0197 0.098 Uiso 1 1 calc R . . H19F H 0.6008 0.1396 0.0702 0.098 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 N1A 0.0318(14) 0.0140(10) 0.0403(13) 0.0003(9) 0.0050(11) 0.0001(10) N2A 0.0434(17) 0.0348(14) 0.0409(15) 0.0020(11) 0.0077(12) -0.0013(12) O1A 0.0706(17) 0.0137(10) 0.111(2) -0.0005(11) 0.0501(15) -0.0013(11) O2A 0.0707(18) 0.0423(14) 0.0847(18) 0.0022(12) 0.0318(14) -0.0172(13) O3A 0.0671(17) 0.0441(14) 0.0712(16) 0.0009(12) 0.0339(13) 0.0080(12) C1A 0.0370(18) 0.0203(14) 0.0425(17) -0.0005(12) 0.0001(14) 0.0021(13) C2A 0.0319(17) 0.0174(13) 0.0372(15) 0.0015(11) -0.0002(13) 0.0023(12) C3A 0.045(2) 0.0192(14) 0.0521(18) 0.0002(13) 0.0103(15) 0.0029(13) C4A 0.0431(19) 0.0270(15) 0.0415(17) -0.0022(12) 0.0073(14) 0.0044(14) C5A 0.0315(17) 0.0273(15) 0.0312(15) 0.0018(11) -0.0004(12) 0.0002(13) C6A 0.0409(19) 0.0210(14) 0.0464(18) 0.0034(12) 0.0025(15) -0.0031(13) C7A 0.0389(18) 0.0169(13) 0.0458(17) -0.0004(11) 0.0021(14) 0.0019(12) C8A 0.0292(17) 0.0156(13) 0.0382(16) -0.0004(11) 0.0036(13) 0.0009(11) C9A 0.0338(18) 0.0247(15) 0.0448(17) 0.0001(12) -0.0011(14) 0.0007(13) C10A 0.0309(19) 0.0382(18) 0.065(2) -0.0003(15) 0.0005(16) -0.0015(14) C11A 0.047(2) 0.0273(16) 0.060(2) -0.0048(14) 0.0242(18) -0.0027(15) C12A 0.057(2) 0.0305(16) 0.0380(17) -0.0006(13) 0.0076(16) -0.0031(16) C13A 0.0393(19) 0.0245(15) 0.0411(17) -0.0007(12) -0.0009(14) -0.0008(13) C14A 0.058(2) 0.060(2) 0.0398(18) 0.0021(16) -0.0130(16) -0.0020(19) C15A 0.115(4) 0.058(3) 0.137(4) -0.013(3) -0.072(3) -0.011(3) C16A 0.107(4) 0.054(3) 0.150(5) 0.018(3) -0.071(3) 0.000(3) C17A 0.040(2) 0.060(2) 0.0459(19) 0.0104(16) -0.0065(15) -0.0012(17) C18A 0.113(4) 0.079(3) 0.080(3) 0.030(2) -0.027(3) 0.011(3) C19A 0.118(4) 0.096(3) 0.044(2) -0.006(2) -0.012(2) -0.032(3) N1B 0.0383(14) 0.0169(11) 0.0332(13) 0.0022(9) 0.0014(11) -0.0001(10) N2B 0.0390(16) 0.0387(15) 0.0421(15) 0.0044(12) 0.0066(12) -0.0026(13) O1B 0.0616(15) 0.0158(9) 0.0471(12) 0.0030(8) 0.0161(10) 0.0025(9) O2B 0.0782(18) 0.0373(13) 0.0713(16) 0.0165(11) 0.0312(14) -0.0009(12) O3B 0.0842(19) 0.0443(14) 0.0704(16) -0.0032(12) 0.0423(14) 0.0064(13) C1B 0.0353(17) 0.0191(14) 0.0372(16) -0.0018(11) 0.0016(13) -0.0008(12) C2B 0.0316(17) 0.0192(13) 0.0337(15) -0.0021(11) -0.0033(12) -0.0016(12) C3B 0.059(2) 0.0199(14) 0.0393(17) -0.0007(12) 0.0087(15) 0.0016(14) C4B 0.057(2) 0.0230(15) 0.0443(18) 0.0035(13) 0.0071(15) -0.0007(14) C5B 0.0273(16) 0.0340(16) 0.0305(15) 0.0000(12) -0.0018(12) -0.0017(13) C6B 0.047(2) 0.0242(15) 0.0489(19) -0.0026(13) 0.0076(15) 0.0036(14) C7B 0.0466(19) 0.0200(14) 0.0493(18) 0.0029(12) 0.0129(15) 0.0034(13) C8B 0.0369(18) 0.0157(13) 0.0326(15) 0.0003(11) 0.0033(13) 0.0007(12) C9B 0.0397(18) 0.0261(15) 0.0365(16) -0.0007(12) -0.0017(14) 0.0045(13) C10B 0.064(3) 0.0413(18) 0.0329(17) 0.0004(13) 0.0010(16) 0.0047(17) C11B 0.065(3) 0.0361(18) 0.0429(19) -0.0021(14) 0.0252(18) -0.0012(17) C12B 0.0365(19) 0.0254(16) 0.068(2) -0.0014(14) 0.0112(17) -0.0033(14) C13B 0.0382(19) 0.0158(13) 0.0468(18) 0.0007(12) -0.0016(14) -0.0013(12) C14B 0.041(2) 0.0416(18) 0.061(2) -0.0010(16) -0.0158(16) -0.0013(16) C15B 0.067(3) 0.101(3) 0.115(4) -0.037(3) -0.044(3) 0.037(3) C16B 0.083(3) 0.046(2) 0.074(3) -0.0178(19) -0.017(2) -0.001(2) C17B 0.039(2) 0.055(2) 0.0421(18) -0.0013(15) -0.0063(15) 0.0050(16) C18B 0.061(3) 0.067(3) 0.109(3) 0.002(2) -0.024(2) 0.018(2) C19B 0.048(2) 0.069(3) 0.078(3) -0.017(2) -0.0138(19) -0.007(2) _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 N1A C1A 1.327(3) . ? N1A C8A 1.432(3) . ? N2A O2A 1.222(3) . ? N2A O3A 1.219(3) . ? N2A C5A 1.461(3) . ? O1A C1A 1.233(3) . ? C1A C2A 1.504(4) . ? C2A C3A 1.388(3) . ? C2A C7A 1.394(3) . ? C3A C4A 1.386(4) . ? C4A C5A 1.381(4) . ? C5A C6A 1.365(4) . ? C6A C7A 1.384(4) . ? C8A C13A 1.390(4) . ? C8A C9A 1.406(4) . ? C9A C10A 1.393(4) . ? C9A C17A 1.520(4) . ? C10A C11A 1.376(4) . ? C11A C12A 1.367(4) . ? C12A C13A 1.385(4) . ? C13A C14A 1.521(4) . ? C14A C16A 1.513(5) . ? C14A C15A 1.513(5) . ? C17A C18A 1.508(5) . ? C17A C19A 1.515(5) . ? N1B C1B 1.339(3) . ? N1B C8B 1.434(3) . ? N2B O2B 1.214(3) . ? N2B O3B 1.214(3) . ? N2B C5B 1.470(3) . ? O1B C1B 1.241(3) . ? C1B C2B 1.503(4) . ? C2B C7B 1.387(3) . ? C2B C3B 1.390(4) . ? C3B C4B 1.390(4) . ? C4B C5B 1.359(4) . ? C5B C6B 1.385(4) . ? C6B C7B 1.359(4) . ? C8B C13B 1.402(4) . ? C8B C9B 1.400(4) . ? C9B C10B 1.389(4) . ? C9B C17B 1.517(4) . ? C10B C11B 1.379(5) . ? C11B C12B 1.370(5) . ? C12B C13B 1.379(4) . ? C13B C14B 1.518(4) . ? C14B C16B 1.511(4) . ? C14B C15B 1.561(5) . ? C17B C18B 1.522(5) . ? C17B C19B 1.524(5) . ? 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 C1A N1A C8A 123.3(2) . . ? O2A N2A O3A 122.8(2) . . ? O2A N2A C5A 118.8(2) . . ? O3A N2A C5A 118.4(2) . . ? O1A C1A N1A 121.0(3) . . ? O1A C1A C2A 120.7(2) . . ? N1A C1A C2A 118.2(2) . . ? C3A C2A C7A 119.5(2) . . ? C3A C2A C1A 117.3(2) . . ? C7A C2A C1A 123.2(2) . . ? C2A C3A C4A 120.7(3) . . ? C5A C4A C3A 118.2(3) . . ? C6A C5A C4A 122.3(2) . . ? C6A C5A N2A 119.5(2) . . ? C4A C5A N2A 118.2(2) . . ? C5A C6A C7A 119.5(2) . . ? C6A C7A C2A 119.8(2) . . ? C13A C8A C9A 122.4(2) . . ? C13A C8A N1A 119.6(3) . . ? C9A C8A N1A 118.0(2) . . ? C10A C9A C8A 116.6(3) . . ? C10A C9A C17A 121.0(3) . . ? C8A C9A C17A 122.4(3) . . ? C11A C10A C9A 121.6(3) . . ? C12A C11A C10A 120.3(3) . . ? C11A C12A C13A 121.1(3) . . ? C12A C13A C8A 118.0(3) . . ? C12A C13A C14A 120.5(3) . . ? C8A C13A C14A 121.4(3) . . ? C16A C14A C15A 111.8(3) . . ? C16A C14A C13A 112.4(3) . . ? C15A C14A C13A 111.2(3) . . ? C18A C17A C19A 111.5(3) . . ? C18A C17A C9A 111.7(3) . . ? C19A C17A C9A 111.4(3) . . ? C1B N1B C8B 122.6(2) . . ? O2B N2B O3B 123.0(2) . . ? O2B N2B C5B 118.8(2) . . ? O3B N2B C5B 118.1(2) . . ? O1B C1B N1B 121.6(2) . . ? O1B C1B C2B 120.4(2) . . ? N1B C1B C2B 118.0(2) . . ? C7B C2B C3B 118.9(2) . . ? C7B C2B C1B 117.7(2) . . ? C3B C2B C1B 123.4(2) . . ? C2B C3B C4B 119.6(3) . . ? C5B C4B C3B 119.5(3) . . ? C4B C5B C6B 122.0(3) . . ? C4B C5B N2B 119.0(2) . . ? C6B C5B N2B 119.0(2) . . ? C7B C6B C5B 118.1(3) . . ? C6B C7B C2B 121.9(3) . . ? C13B C8B C9B 121.9(2) . . ? C13B C8B N1B 119.1(2) . . ? C9B C8B N1B 118.9(3) . . ? C10B C9B C8B 117.6(3) . . ? C10B C9B C17B 119.7(3) . . ? C8B C9B C17B 122.6(3) . . ? C11B C10B C9B 120.9(3) . . ? C12B C11B C10B 120.3(3) . . ? C11B C12B C13B 121.5(3) . . ? C12B C13B C8B 117.8(3) . . ? C12B C13B C14B 121.6(3) . . ? C8B C13B C14B 120.6(3) . . ? C16B C14B C13B 110.9(3) . . ? C16B C14B C15B 109.5(3) . . ? C13B C14B C15B 111.5(3) . . ? C9B C17B C18B 111.6(3) . . ? C9B C17B C19B 111.4(3) . . ? C18B C17B C19B 111.8(3) . . ? 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 C8A N1A C1A O1A -0.5(4) . . . . ? C8A N1A C1A C2A 176.7(3) . . . . ? O1A C1A C2A C3A -0.9(4) . . . . ? N1A C1A C2A C3A -178.1(3) . . . . ? O1A C1A C2A C7A 178.2(3) . . . . ? N1A C1A C2A C7A 1.0(4) . . . . ? C7A C2A C3A C4A -0.8(4) . . . . ? C1A C2A C3A C4A 178.3(3) . . . . ? C2A C3A C4A C5A 1.1(4) . . . . ? C3A C4A C5A C6A -0.7(4) . . . . ? C3A C4A C5A N2A 179.2(3) . . . . ? O2A N2A C5A C6A 4.3(4) . . . . ? O3A N2A C5A C6A -175.1(3) . . . . ? O2A N2A C5A C4A -175.6(3) . . . . ? O3A N2A C5A C4A 5.0(4) . . . . ? C4A C5A C6A C7A 0.0(4) . . . . ? N2A C5A C6A C7A -179.9(3) . . . . ? C5A C6A C7A C2A 0.2(4) . . . . ? C3A C2A C7A C6A 0.2(4) . . . . ? C1A C2A C7A C6A -179.0(3) . . . . ? C1A N1A C8A C13A 89.9(3) . . . . ? C1A N1A C8A C9A -92.8(3) . . . . ? C13A C8A C9A C10A 2.1(4) . . . . ? N1A C8A C9A C10A -175.1(2) . . . . ? C13A C8A C9A C17A -178.3(3) . . . . ? N1A C8A C9A C17A 4.5(4) . . . . ? C8A C9A C10A C11A -0.6(4) . . . . ? C17A C9A C10A C11A 179.8(3) . . . . ? C9A C10A C11A C12A -1.0(4) . . . . ? C10A C11A C12A C13A 1.1(4) . . . . ? C11A C12A C13A C8A 0.4(4) . . . . ? C11A C12A C13A C14A 178.1(3) . . . . ? C9A C8A C13A C12A -2.1(4) . . . . ? N1A C8A C13A C12A 175.1(2) . . . . ? C9A C8A C13A C14A -179.7(3) . . . . ? N1A C8A C13A C14A -2.6(4) . . . . ? C12A C13A C14A C16A 55.2(4) . . . . ? C8A C13A C14A C16A -127.2(3) . . . . ? C12A C13A C14A C15A -71.1(4) . . . . ? C8A C13A C14A C15A 106.6(4) . . . . ? C10A C9A C17A C18A 68.1(4) . . . . ? C8A C9A C17A C18A -111.4(3) . . . . ? C10A C9A C17A C19A -57.3(4) . . . . ? C8A C9A C17A C19A 123.1(3) . . . . ? C8B N1B C1B O1B -3.1(4) . . . . ? C8B N1B C1B C2B 175.3(2) . . . . ? O1B C1B C2B C7B -3.7(4) . . . . ? N1B C1B C2B C7B 177.7(3) . . . . ? O1B C1B C2B C3B 174.0(3) . . . . ? N1B C1B C2B C3B -4.5(4) . . . . ? C7B C2B C3B C4B -0.2(4) . . . . ? C1B C2B C3B C4B -177.9(3) . . . . ? C2B C3B C4B C5B 0.6(5) . . . . ? C3B C4B C5B C6B -1.2(5) . . . . ? C3B C4B C5B N2B 180.0(3) . . . . ? O2B N2B C5B C4B -6.6(4) . . . . ? O3B N2B C5B C4B 173.8(3) . . . . ? O2B N2B C5B C6B 174.6(3) . . . . ? O3B N2B C5B C6B -5.0(4) . . . . ? C4B C5B C6B C7B 1.3(5) . . . . ? N2B C5B C6B C7B -179.9(3) . . . . ? C5B C6B C7B C2B -0.9(5) . . . . ? C3B C2B C7B C6B 0.3(5) . . . . ? C1B C2B C7B C6B 178.2(3) . . . . ? C1B N1B C8B C13B 104.5(3) . . . . ? C1B N1B C8B C9B -78.8(3) . . . . ? C13B C8B C9B C10B -1.6(4) . . . . ? N1B C8B C9B C10B -178.1(2) . . . . ? C13B C8B C9B C17B 176.5(3) . . . . ? N1B C8B C9B C17B 0.0(4) . . . . ? C8B C9B C10B C11B 1.4(4) . . . . ? C17B C9B C10B C11B -176.8(3) . . . . ? C9B C10B C11B C12B -0.7(5) . . . . ? C10B C11B C12B C13B 0.1(4) . . . . ? C11B C12B C13B C8B -0.3(4) . . . . ? C11B C12B C13B C14B 177.9(3) . . . . ? C9B C8B C13B C12B 1.1(4) . . . . ? N1B C8B C13B C12B 177.6(2) . . . . ? C9B C8B C13B C14B -177.2(2) . . . . ? N1B C8B C13B C14B -0.7(4) . . . . ? C12B C13B C14B C16B 95.2(3) . . . . ? C8B C13B C14B C16B -86.6(3) . . . . ? C12B C13B C14B C15B -27.2(4) . . . . ? C8B C13B C14B C15B 151.0(3) . . . . ? C10B C9B C17B C18B -65.1(4) . . . . ? C8B C9B C17B C18B 116.7(3) . . . . ? C10B C9B C17B C19B 60.6(4) . . . . ? C8B C9B C17B C19B -117.5(3) . . . . ? _diffrn_measured_fraction_theta_max 0.955 _diffrn_reflns_theta_full 28.31 _diffrn_measured_fraction_theta_full 0.955 _refine_diff_density_max 0.454 _refine_diff_density_min -0.218 _refine_diff_density_rms 0.059 data_gah11 _database_code_CSD 158581 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H18 N2 O3' _chemical_formula_weight 298.33 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 5.712(2) _cell_length_b 10.575(3) _cell_length_c 12.798(5) _cell_angle_alpha 88.08(3) _cell_angle_beta 77.96(2) _cell_angle_gamma 85.32(3) _cell_volume 753.4(4) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.315 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 316 _exptl_absorpt_coefficient_mu 0.091 _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 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 2221 _diffrn_reflns_av_R_equivalents 0.1132 _diffrn_reflns_av_sigmaI/netI 0.0847 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_h_max 2 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.63 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1365 _reflns_number_gt 1128 _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^)+(0.0966P)^2^+0.0328P] 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 1365 _refine_ls_number_parameters 199 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0698 _refine_ls_R_factor_gt 0.0613 _refine_ls_wR_factor_ref 0.1605 _refine_ls_wR_factor_gt 0.1502 _refine_ls_goodness_of_fit_ref 1.084 _refine_ls_restrained_S_all 1.084 _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 O1 O 0.1444(10) -0.3897(3) -0.1028(2) 0.057(3) Uani 1 1 d . . . O2 O -0.2069(8) -0.6746(2) -0.5631(2) 0.0919(16) Uani 1 1 d . . . O3 O 0.1186(7) -0.7630(3) -0.5266(2) 0.0959(16) Uani 1 1 d . . . N1 N -0.2302(8) -0.40941(19) -0.13038(19) 0.046(2) Uani 1 1 d . . . H1AB H -0.3797 -0.3909 -0.1038 0.056 Uiso 1 1 calc R . . N2 N -0.0604(10) -0.6908(2) -0.5060(2) 0.0682(18) Uani 1 1 d . . . C1 C -0.1795(8) -0.4824(2) -0.2235(2) 0.0380(17) Uani 1 1 d . . . C2 C -0.3475(8) -0.4718(2) -0.2873(2) 0.0484(18) Uani 1 1 d . . . H2AB H -0.4867 -0.4185 -0.2682 0.058 Uiso 1 1 calc R . . C3 C -0.3076(8) -0.5411(3) -0.3798(2) 0.0547(17) Uani 1 1 d . . . H3AB H -0.4192 -0.5340 -0.4237 0.066 Uiso 1 1 calc R . . C4 C -0.1053(8) -0.6194(2) -0.4065(2) 0.0432(18) Uani 1 1 d . . . C5 C 0.0637(9) -0.6320(2) -0.3434(2) 0.0491(17) Uani 1 1 d . . . H5AB H 0.2020 -0.6859 -0.3628 0.059 Uiso 1 1 calc R . . C6 C 0.0237(8) -0.5633(2) -0.2512(2) 0.0471(16) Uani 1 1 d . . . H6AB H 0.1349 -0.5716 -0.2072 0.056 Uiso 1 1 calc R . . C7 C -0.0732(16) -0.3646(3) -0.0773(3) 0.041(3) Uani 1 1 d . . . C8 C -0.1830(8) -0.2789(2) 0.0126(2) 0.0396(18) Uani 1 1 d . . . C9 C -0.4118(8) -0.2853(2) 0.0711(2) 0.0472(18) Uani 1 1 d . . . H9AB H -0.5065 -0.3465 0.0553 0.057 Uiso 1 1 calc R . . C10 C -0.5039(8) -0.2025(2) 0.1531(2) 0.0512(16) Uani 1 1 d . . . H10B H -0.6592 -0.2098 0.1919 0.061 Uiso 1 1 calc R . . C11 C -0.3715(8) -0.1085(2) 0.1793(2) 0.0376(17) Uani 1 1 d . . . C12 C -0.1413(9) -0.1042(3) 0.1204(3) 0.0495(18) Uani 1 1 d . . . H12B H -0.0460 -0.0430 0.1359 0.059 Uiso 1 1 calc R . . C13 C -0.0478(8) -0.1874(3) 0.0393(2) 0.0512(17) Uani 1 1 d . . . H13B H 0.1092 -0.1819 0.0019 0.061 Uiso 1 1 calc R . . C14 C -0.4810(8) -0.0100(2) 0.2652(2) 0.0435(16) Uani 1 1 d . . . C15 C -0.6616(8) -0.0673(3) 0.3551(2) 0.079(2) Uani 1 1 d . . . H15D H -0.7824 -0.1034 0.3259 0.118 Uiso 1 1 calc R . . H15E H -0.7356 -0.0024 0.4045 0.118 Uiso 1 1 calc R . . H15F H -0.5807 -0.1324 0.3916 0.118 Uiso 1 1 calc R . . C16 C -0.6108(8) 0.0972(3) 0.2110(3) 0.0718(19) Uani 1 1 d . . . H16D H -0.7288 0.0630 0.1788 0.108 Uiso 1 1 calc R . . H16E H -0.4967 0.1375 0.1570 0.108 Uiso 1 1 calc R . . H16F H -0.6883 0.1584 0.2633 0.108 Uiso 1 1 calc R . . C17 C -0.2929(10) 0.0437(4) 0.3158(4) 0.098(2) Uani 1 1 d . . . H17D H -0.3698 0.1043 0.3688 0.147 Uiso 1 1 calc R . . H17E H -0.1799 0.0846 0.2618 0.147 Uiso 1 1 calc R . . H17F H -0.2102 -0.0239 0.3490 0.147 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 O1 0.037(8) 0.0796(15) 0.0570(15) -0.0223(12) -0.011(2) -0.009(2) O2 0.143(5) 0.0908(16) 0.0531(15) -0.0144(12) -0.039(2) -0.0239(19) O3 0.128(5) 0.0822(16) 0.0686(16) -0.0324(13) 0.0002(18) 0.003(2) N1 0.052(7) 0.0532(12) 0.0354(13) -0.0086(10) -0.0115(17) -0.0002(16) N2 0.108(6) 0.0526(14) 0.0429(15) -0.0052(11) -0.007(2) -0.020(2) C1 0.039(5) 0.0426(12) 0.0347(14) 0.0011(10) -0.0120(18) -0.0080(17) C2 0.050(6) 0.0531(14) 0.0456(16) -0.0044(11) -0.018(2) 0.0003(18) C3 0.070(6) 0.0589(15) 0.0413(15) 0.0018(12) -0.0245(19) -0.012(2) C4 0.049(6) 0.0447(13) 0.0372(15) -0.0019(11) -0.008(2) -0.0138(19) C5 0.045(5) 0.0467(13) 0.0553(18) -0.0052(11) -0.010(2) 0.0006(17) C6 0.052(5) 0.0457(13) 0.0494(15) -0.0035(11) -0.0249(19) -0.0005(19) C7 0.042(10) 0.0491(15) 0.0347(17) 0.0003(12) -0.013(2) -0.005(2) C8 0.042(6) 0.0466(13) 0.0333(14) 0.0020(10) -0.0150(19) -0.0050(18) C9 0.052(6) 0.0518(13) 0.0433(16) -0.0049(11) -0.016(2) -0.0171(19) C10 0.052(5) 0.0580(14) 0.0455(15) -0.0111(11) -0.0097(18) -0.0144(19) C11 0.033(6) 0.0487(13) 0.0355(15) -0.0016(10) -0.0177(19) -0.0028(18) C12 0.047(6) 0.0558(14) 0.0520(18) -0.0120(12) -0.019(2) -0.0165(19) C13 0.045(5) 0.0661(16) 0.0451(15) -0.0095(12) -0.0093(19) -0.015(2) C14 0.038(5) 0.0513(13) 0.0473(15) -0.0094(11) -0.0199(18) -0.0083(17) C15 0.121(6) 0.0600(16) 0.0438(16) -0.0071(12) 0.004(2) 0.005(2) C16 0.099(6) 0.0529(14) 0.0608(18) -0.0014(13) -0.015(2) 0.007(2) C17 0.068(7) 0.137(3) 0.101(3) -0.078(3) -0.038(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 O1 C7 1.227(9) . ? O2 N2 1.219(5) . ? O3 N2 1.214(5) . ? N1 C7 1.355(9) . ? N1 C1 1.407(3) . ? N2 C4 1.468(4) . ? C1 C6 1.375(5) . ? C1 C2 1.380(5) . ? C2 C3 1.381(4) . ? C3 C4 1.355(5) . ? C4 C5 1.378(5) . ? C5 C6 1.375(4) . ? C7 C8 1.489(5) . ? C8 C9 1.369(5) . ? C8 C13 1.380(5) . ? C9 C10 1.379(4) . ? C10 C11 1.387(5) . ? C11 C12 1.376(5) . ? C11 C14 1.538(4) . ? C12 C13 1.375(4) . ? C14 C17 1.521(6) . ? C14 C15 1.522(5) . ? C14 C16 1.530(4) . ? 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 C7 N1 C1 128.2(5) . . ? O3 N2 O2 123.7(3) . . ? O3 N2 C4 118.5(4) . . ? O2 N2 C4 117.9(4) . . ? C6 C1 C2 119.9(3) . . ? C6 C1 N1 123.1(3) . . ? C2 C1 N1 116.9(3) . . ? C3 C2 C1 119.5(4) . . ? C4 C3 C2 119.8(4) . . ? C3 C4 C5 121.6(3) . . ? C3 C4 N2 119.7(4) . . ? C5 C4 N2 118.7(4) . . ? C6 C5 C4 118.7(4) . . ? C5 C6 C1 120.5(4) . . ? O1 C7 N1 122.8(4) . . ? O1 C7 C8 122.0(7) . . ? N1 C7 C8 115.1(7) . . ? C9 C8 C13 117.6(3) . . ? C9 C8 C7 123.8(4) . . ? C13 C8 C7 118.6(5) . . ? C8 C9 C10 121.1(4) . . ? C9 C10 C11 121.9(4) . . ? C12 C11 C10 116.3(3) . . ? C12 C11 C14 121.9(3) . . ? C10 C11 C14 121.7(4) . . ? C13 C12 C11 122.0(4) . . ? C12 C13 C8 121.1(4) . . ? C17 C14 C15 107.1(3) . . ? C17 C14 C16 109.6(3) . . ? C15 C14 C16 108.8(3) . . ? C17 C14 C11 112.6(4) . . ? C15 C14 C11 111.4(2) . . ? C16 C14 C11 107.3(2) . . ? 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 C7 N1 C1 C6 28.2(4) . . . . ? C7 N1 C1 C2 -153.0(3) . . . . ? C6 C1 C2 C3 -1.2(4) . . . . ? N1 C1 C2 C3 180.0(3) . . . . ? C1 C2 C3 C4 0.6(5) . . . . ? C2 C3 C4 C5 -0.1(5) . . . . ? C2 C3 C4 N2 -178.6(3) . . . . ? O3 N2 C4 C3 -177.9(3) . . . . ? O2 N2 C4 C3 1.5(5) . . . . ? O3 N2 C4 C5 3.5(4) . . . . ? O2 N2 C4 C5 -177.0(3) . . . . ? C3 C4 C5 C6 0.2(5) . . . . ? N2 C4 C5 C6 178.8(2) . . . . ? C4 C5 C6 C1 -0.9(4) . . . . ? C2 C1 C6 C5 1.4(4) . . . . ? N1 C1 C6 C5 -179.9(3) . . . . ? C1 N1 C7 O1 -4.2(4) . . . . ? C1 N1 C7 C8 174.0(2) . . . . ? O1 C7 C8 C9 -153.2(3) . . . . ? N1 C7 C8 C9 28.6(4) . . . . ? O1 C7 C8 C13 26.7(4) . . . . ? N1 C7 C8 C13 -151.4(3) . . . . ? C13 C8 C9 C10 0.5(5) . . . . ? C7 C8 C9 C10 -179.5(3) . . . . ? C8 C9 C10 C11 0.7(5) . . . . ? C9 C10 C11 C12 -1.3(5) . . . . ? C9 C10 C11 C14 175.4(3) . . . . ? C10 C11 C12 C13 0.6(5) . . . . ? C14 C11 C12 C13 -176.1(3) . . . . ? C11 C12 C13 C8 0.7(5) . . . . ? C9 C8 C13 C12 -1.2(5) . . . . ? C7 C8 C13 C12 178.8(3) . . . . ? C12 C11 C14 C17 -28.9(4) . . . . ? C10 C11 C14 C17 154.6(3) . . . . ? C12 C11 C14 C15 -149.2(3) . . . . ? C10 C11 C14 C15 34.3(4) . . . . ? C12 C11 C14 C16 91.8(4) . . . . ? C10 C11 C14 C16 -84.7(4) . . . . ? _diffrn_measured_fraction_theta_max 0.513 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.513 _refine_diff_density_max 0.206 _refine_diff_density_min -0.216 _refine_diff_density_rms 0.066 data_gah12 _database_code_CSD 158582 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18.33 H20.33 Cl0.33 N2 O3' _chemical_formula_weight 328.52 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 ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 12.782(5) _cell_length_b 14.751(6) _cell_length_c 15.297(6) _cell_angle_alpha 117.470(8) _cell_angle_beta 92.146(8) _cell_angle_gamma 95.081(8) _cell_volume 2539.1(17) _cell_formula_units_Z 6 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.289 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1044 _exptl_absorpt_coefficient_mu 0.139 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 16367 _diffrn_reflns_av_R_equivalents 0.0815 _diffrn_reflns_av_sigmaI/netI 0.2848 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.51 _diffrn_reflns_theta_max 28.46 _reflns_number_total 11809 _reflns_number_gt 3222 _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^)+(0.0776P)^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 11809 _refine_ls_number_parameters 640 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1980 _refine_ls_R_factor_gt 0.0661 _refine_ls_wR_factor_ref 0.1951 _refine_ls_wR_factor_gt 0.1465 _refine_ls_goodness_of_fit_ref 0.722 _refine_ls_restrained_S_all 0.722 _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 O1 O 0.3713(2) 0.56776(19) 0.31372(18) 0.0357(7) Uani 1 1 d . . . O2 O 0.3283(3) 1.0699(2) 0.3395(3) 0.0630(10) Uani 1 1 d . . . O3 O 0.4082(3) 0.9767(2) 0.2140(2) 0.0605(10) Uani 1 1 d . . . N1 N 0.3541(3) 0.9866(3) 0.2803(3) 0.0448(10) Uani 1 1 d . . . N2 N 0.2167(3) 0.6374(2) 0.3252(2) 0.0315(8) Uani 1 1 d . . . H2A H 0.1509 0.6303 0.3338 0.038 Uiso 1 1 calc R . . C1 C 0.3190(3) 0.8952(3) 0.2909(3) 0.0361(10) Uani 1 1 d . . . C2 C 0.3609(3) 0.8045(3) 0.2366(3) 0.0347(10) Uani 1 1 d . . . H2B H 0.4103 0.8006 0.1922 0.042 Uiso 1 1 calc R . . C3 C 0.3287(3) 0.7198(3) 0.2487(3) 0.0354(10) Uani 1 1 d . . . H3A H 0.3567 0.6585 0.2121 0.042 Uiso 1 1 calc R . . C4 C 0.2545(3) 0.7246(3) 0.3154(3) 0.0321(10) Uani 1 1 d . . . C5 C 0.2105(3) 0.8171(3) 0.3718(3) 0.0326(10) Uani 1 1 d . . . C6 C 0.2438(3) 0.9016(3) 0.3577(3) 0.0372(11) Uani 1 1 d . . . H6A H 0.2158 0.9632 0.3930 0.045 Uiso 1 1 calc R . . C7 C 0.1350(3) 0.8261(3) 0.4463(3) 0.0435(12) Uani 1 1 d . . . H7A H 0.1142 0.8942 0.4766 0.065 Uiso 1 1 calc R . . H7B H 0.1682 0.8131 0.4961 0.065 Uiso 1 1 calc R . . H7C H 0.0739 0.7767 0.4144 0.065 Uiso 1 1 calc R . . C8 C 0.2760(3) 0.5620(3) 0.3224(3) 0.0332(10) Uani 1 1 d . . . C9 C 0.2168(3) 0.4737(3) 0.3278(3) 0.0313(10) Uani 1 1 d . . . C10 C 0.2707(3) 0.3898(3) 0.3144(3) 0.0349(10) Uani 1 1 d . . . H10A H 0.3423 0.3927 0.3056 0.042 Uiso 1 1 calc R . . C11 C 0.2198(3) 0.3039(3) 0.3141(3) 0.0405(11) Uani 1 1 d . . . H11A H 0.2582 0.2500 0.3051 0.049 Uiso 1 1 calc R . . C12 C 0.1123(3) 0.2940(3) 0.3266(3) 0.0325(10) Uani 1 1 d . . . C13 C 0.0604(3) 0.3794(3) 0.3427(3) 0.0441(12) Uani 1 1 d . . . H13A H -0.0108 0.3772 0.3530 0.053 Uiso 1 1 calc R . . C14 C 0.1109(3) 0.4665(3) 0.3438(3) 0.0414(11) Uani 1 1 d . . . H14A H 0.0733 0.5216 0.3556 0.050 Uiso 1 1 calc R . . C15 C 0.0557(3) 0.1967(3) 0.3226(3) 0.0367(11) Uani 1 1 d . . . C16 C 0.0758(4) 0.1024(3) 0.2264(3) 0.0492(13) Uani 1 1 d . . . H16A H 0.0486 0.1090 0.1706 0.074 Uiso 1 1 calc R . . H16B H 0.0412 0.0411 0.2248 0.074 Uiso 1 1 calc R . . H16C H 0.1503 0.0982 0.2239 0.074 Uiso 1 1 calc R . . C17 C 0.0993(4) 0.1845(3) 0.4120(3) 0.0434(11) Uani 1 1 d . . . H17A H 0.0879 0.2434 0.4723 0.065 Uiso 1 1 calc R . . H17B H 0.1735 0.1790 0.4088 0.065 Uiso 1 1 calc R . . H17C H 0.0636 0.1235 0.4101 0.065 Uiso 1 1 calc R . . C18 C -0.0635(3) 0.1997(3) 0.3284(3) 0.0445(12) Uani 1 1 d . . . H18A H -0.0766 0.2582 0.3884 0.067 Uiso 1 1 calc R . . H18B H -0.0951 0.1379 0.3277 0.067 Uiso 1 1 calc R . . H18C H -0.0935 0.2050 0.2726 0.067 Uiso 1 1 calc R . . O1B O 0.6431(2) 0.4748(2) 0.05851(19) 0.0385(7) Uani 1 1 d . . . O2B O 0.9025(3) 0.9266(2) 0.4241(2) 0.0574(9) Uani 1 1 d . . . O3B O 0.8827(3) 0.9409(2) 0.2907(2) 0.0597(9) Uani 1 1 d . . . N1B N 0.8580(3) 0.9012(3) 0.3425(3) 0.0432(10) Uani 1 1 d . . . N2B N 0.5487(2) 0.5592(2) 0.1895(2) 0.0302(8) Uani 1 1 d . . . H2BA H 0.4930 0.5562 0.2183 0.036 Uiso 1 1 calc R . . C1B C 0.7703(3) 0.8180(3) 0.3046(3) 0.0350(10) Uani 1 1 d . . . C2B C 0.7314(3) 0.7759(3) 0.2072(3) 0.0369(11) Uani 1 1 d . . . H2BB H 0.7563 0.8026 0.1665 0.044 Uiso 1 1 calc R . . C3B C 0.6545(3) 0.6930(3) 0.1719(3) 0.0339(10) Uani 1 1 d . . . H3BA H 0.6263 0.6645 0.1065 0.041 Uiso 1 1 calc R . . C4B C 0.6180(3) 0.6511(3) 0.2309(3) 0.0267(9) Uani 1 1 d . . . C5B C 0.6538(3) 0.6984(3) 0.3322(3) 0.0320(10) Uani 1 1 d . . . C6B C 0.7314(3) 0.7814(3) 0.3660(3) 0.0330(10) Uani 1 1 d . . . H6BA H 0.7578 0.8131 0.4321 0.040 Uiso 1 1 calc R . . C7B C 0.6111(3) 0.6591(3) 0.4002(3) 0.0431(11) Uani 1 1 d . . . H7BA H 0.6445 0.7010 0.4659 0.065 Uiso 1 1 calc R . . H7BB H 0.6251 0.5892 0.3773 0.065 Uiso 1 1 calc R . . H7BC H 0.5364 0.6620 0.4010 0.065 Uiso 1 1 calc R . . C8B C 0.5669(3) 0.4735(3) 0.1042(3) 0.0324(10) Uani 1 1 d . . . C9B C 0.4940(3) 0.3784(3) 0.0711(3) 0.0292(9) Uani 1 1 d . . . C10B C 0.5296(3) 0.2844(3) 0.0119(3) 0.0338(10) Uani 1 1 d . . . H10C H 0.5982 0.2833 -0.0066 0.041 Uiso 1 1 calc R . . C11B C 0.4661(3) 0.1933(3) -0.0196(3) 0.0359(10) Uani 1 1 d . . . H11C H 0.4933 0.1321 -0.0584 0.043 Uiso 1 1 calc R . . C12B C 0.3616(3) 0.1890(3) 0.0045(3) 0.0338(10) Uani 1 1 d . . . C13B C 0.3249(3) 0.2840(3) 0.0626(3) 0.0348(10) Uani 1 1 d . . . H13C H 0.2557 0.2851 0.0794 0.042 Uiso 1 1 calc R . . C14B C 0.3890(3) 0.3756(3) 0.0953(3) 0.0341(10) Uani 1 1 d . . . H14B H 0.3623 0.4370 0.1342 0.041 Uiso 1 1 calc R . . C15B C 0.2962(3) 0.0865(3) -0.0232(3) 0.0387(11) Uani 1 1 d . . . C16B C 0.3079(4) 0.0070(3) -0.1315(3) 0.0583(14) Uani 1 1 d . . . H16D H 0.2828 0.0321 -0.1753 0.087 Uiso 1 1 calc R . . H16E H 0.2674 -0.0572 -0.1467 0.087 Uiso 1 1 calc R . . H16F H 0.3808 -0.0030 -0.1397 0.087 Uiso 1 1 calc R . . C17B C 0.3348(4) 0.0474(4) 0.0487(4) 0.0673(16) Uani 1 1 d . . . H17G H 0.3261 0.0969 0.1154 0.101 Uiso 1 1 calc R . . H17H H 0.4080 0.0379 0.0422 0.101 Uiso 1 1 calc R . . H17I H 0.2945 -0.0170 0.0333 0.101 Uiso 1 1 calc R . . C18B C 0.1802(3) 0.0959(3) -0.0147(3) 0.0479(12) Uani 1 1 d . . . H18G H 0.1548 0.1201 -0.0591 0.072 Uiso 1 1 calc R . . H18H H 0.1693 0.1437 0.0519 0.072 Uiso 1 1 calc R . . H18I H 0.1428 0.0298 -0.0317 0.072 Uiso 1 1 calc R . . O1C O 0.9844(2) 0.6133(2) 0.2866(2) 0.0436(8) Uani 1 1 d . . . O2C O 1.0549(3) 0.7738(3) -0.1024(3) 0.0714(11) Uani 1 1 d . . . O3C O 1.1604(4) 0.8546(4) 0.0304(3) 0.124(2) Uani 1 1 d . . . N1C N 1.0839(4) 0.7925(3) -0.0184(4) 0.0617(12) Uani 1 1 d . . . N2C N 0.8715(3) 0.5677(2) 0.1504(2) 0.0343(8) Uani 1 1 d . . . H2CA H 0.8127 0.5324 0.1191 0.041 Uiso 1 1 calc R . . C1C C 1.0289(4) 0.7341(3) 0.0265(3) 0.0426(11) Uani 1 1 d . . . C2C C 1.0466(3) 0.7698(3) 0.1281(3) 0.0455(12) Uani 1 1 d . . . H2CB H 1.0930 0.8285 0.1673 0.055 Uiso 1 1 calc R . . C3C C 0.9932(3) 0.7153(3) 0.1680(3) 0.0379(11) Uani 1 1 d . . . H3CA H 1.0021 0.7392 0.2360 0.045 Uiso 1 1 calc R . . C4C C 0.9260(3) 0.6254(3) 0.1105(3) 0.0337(10) Uani 1 1 d . . . C5C C 0.9101(3) 0.5901(3) 0.0070(3) 0.0326(10) Uani 1 1 d . . . C6C C 0.9623(3) 0.6469(3) -0.0335(3) 0.0411(11) Uani 1 1 d . . . H6CA H 0.9521 0.6257 -0.1010 0.049 Uiso 1 1 calc R . . C7C C 0.8381(3) 0.4932(3) -0.0584(3) 0.0415(11) Uani 1 1 d . . . H7CA H 0.8372 0.4811 -0.1257 0.062 Uiso 1 1 calc R . . H7CB H 0.7680 0.5007 -0.0376 0.062 Uiso 1 1 calc R . . H7CC H 0.8631 0.4360 -0.0535 0.062 Uiso 1 1 calc R . . C8C C 0.9038(3) 0.5628(3) 0.2350(3) 0.0322(10) Uani 1 1 d . . . C9C C 0.8371(3) 0.4926(3) 0.2585(3) 0.0301(10) Uani 1 1 d . . . C10C C 0.8335(3) 0.5155(3) 0.3573(3) 0.0358(10) Uani 1 1 d . . . H10B H 0.8774 0.5711 0.4058 0.043 Uiso 1 1 calc R . . C11C C 0.7647(3) 0.4556(3) 0.3841(3) 0.0358(10) Uani 1 1 d . . . H11B H 0.7635 0.4731 0.4507 0.043 Uiso 1 1 calc R . . C12C C 0.6979(3) 0.3709(3) 0.3152(3) 0.0307(10) Uani 1 1 d . . . C13C C 0.7088(3) 0.3445(3) 0.2152(3) 0.0372(11) Uani 1 1 d . . . H13B H 0.6696 0.2854 0.1661 0.045 Uiso 1 1 calc R . . C14C C 0.7764(3) 0.4041(3) 0.1880(3) 0.0322(10) Uani 1 1 d . . . H14C H 0.7811 0.3845 0.1213 0.039 Uiso 1 1 calc R . . C15C C 0.6164(3) 0.3136(3) 0.3476(3) 0.0331(10) Uani 1 1 d . . . C16C C 0.6717(4) 0.2571(3) 0.3957(3) 0.0511(13) Uani 1 1 d . . . H16G H 0.7201 0.3056 0.4501 0.077 Uiso 1 1 calc R . . H16H H 0.7095 0.2059 0.3478 0.077 Uiso 1 1 calc R . . H16I H 0.6200 0.2245 0.4194 0.077 Uiso 1 1 calc R . . C17C C 0.5385(3) 0.2360(3) 0.2622(3) 0.0482(12) Uani 1 1 d . . . H17D H 0.5029 0.2709 0.2324 0.072 Uiso 1 1 calc R . . H17E H 0.4876 0.2035 0.2868 0.072 Uiso 1 1 calc R . . H17F H 0.5758 0.1847 0.2137 0.072 Uiso 1 1 calc R . . C18C C 0.5506(3) 0.3919(3) 0.4237(3) 0.0441(12) Uani 1 1 d . . . H18D H 0.5967 0.4422 0.4793 0.066 Uiso 1 1 calc R . . H18E H 0.5003 0.3565 0.4458 0.066 Uiso 1 1 calc R . . H18F H 0.5142 0.4258 0.3933 0.066 Uiso 1 1 calc R . . C50 C 0.4946(10) 0.0727(7) 0.5215(9) 0.211(5) Uani 1 1 d . . . H50A H 0.4419 0.0986 0.4956 0.253 Uiso 0.50 1 d PR . . H50B H 0.5386 0.1308 0.5721 0.253 Uiso 0.50 1 d PR . . Cl1S Cl 0.57042(16) 0.00000(18) 0.42491(15) 0.1249(7) 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 O1 0.0192(18) 0.0469(18) 0.0452(17) 0.0236(14) 0.0086(13) 0.0092(13) O2 0.061(3) 0.043(2) 0.096(3) 0.037(2) 0.022(2) 0.0213(18) O3 0.064(3) 0.070(2) 0.071(2) 0.050(2) 0.033(2) 0.0179(19) N1 0.039(3) 0.045(3) 0.059(3) 0.032(2) -0.002(2) 0.008(2) N2 0.020(2) 0.039(2) 0.044(2) 0.0247(17) 0.0085(16) 0.0094(16) C1 0.029(3) 0.041(3) 0.041(3) 0.023(2) -0.003(2) 0.004(2) C2 0.024(3) 0.047(3) 0.036(2) 0.021(2) 0.0102(19) 0.011(2) C3 0.028(3) 0.040(3) 0.040(3) 0.019(2) 0.006(2) 0.007(2) C4 0.025(3) 0.041(3) 0.031(2) 0.017(2) -0.0048(19) 0.005(2) C5 0.026(3) 0.038(3) 0.033(2) 0.016(2) -0.0037(19) 0.006(2) C6 0.030(3) 0.039(3) 0.038(2) 0.013(2) 0.002(2) 0.014(2) C7 0.040(3) 0.052(3) 0.042(3) 0.023(2) 0.013(2) 0.014(2) C8 0.033(3) 0.041(3) 0.025(2) 0.0144(19) 0.002(2) 0.006(2) C9 0.025(3) 0.039(2) 0.035(2) 0.021(2) 0.0029(19) 0.007(2) C10 0.019(2) 0.044(3) 0.045(3) 0.022(2) 0.0039(19) 0.009(2) C11 0.029(3) 0.044(3) 0.056(3) 0.027(2) 0.009(2) 0.017(2) C12 0.023(3) 0.041(3) 0.037(2) 0.021(2) -0.0012(19) 0.007(2) C13 0.023(3) 0.051(3) 0.071(3) 0.038(3) 0.006(2) 0.013(2) C14 0.029(3) 0.045(3) 0.066(3) 0.037(2) 0.007(2) 0.017(2) C15 0.030(3) 0.049(3) 0.043(3) 0.028(2) 0.004(2) 0.015(2) C16 0.051(3) 0.048(3) 0.046(3) 0.019(2) 0.006(2) 0.005(2) C17 0.045(3) 0.045(3) 0.048(3) 0.027(2) 0.002(2) 0.009(2) C18 0.026(3) 0.055(3) 0.063(3) 0.037(2) 0.004(2) 0.003(2) O1B 0.0297(19) 0.0447(18) 0.0412(17) 0.0190(14) 0.0105(14) 0.0080(14) O2B 0.046(2) 0.062(2) 0.062(2) 0.0313(18) -0.0219(18) -0.0054(17) O3B 0.054(2) 0.058(2) 0.070(2) 0.0358(19) -0.0022(18) -0.0122(17) N1B 0.037(3) 0.035(2) 0.063(3) 0.026(2) 0.007(2) 0.0073(18) N2B 0.018(2) 0.039(2) 0.0372(19) 0.0199(17) 0.0060(15) 0.0092(16) C1B 0.033(3) 0.028(2) 0.048(3) 0.020(2) 0.000(2) 0.006(2) C2B 0.040(3) 0.036(2) 0.041(3) 0.023(2) 0.001(2) 0.008(2) C3B 0.036(3) 0.035(2) 0.030(2) 0.0141(19) -0.0044(19) 0.011(2) C4B 0.020(2) 0.028(2) 0.038(2) 0.0177(19) 0.0076(19) 0.0125(18) C5B 0.025(3) 0.037(2) 0.040(2) 0.021(2) 0.007(2) 0.015(2) C6B 0.025(3) 0.038(2) 0.037(2) 0.017(2) -0.0016(19) 0.008(2) C7B 0.036(3) 0.052(3) 0.046(3) 0.027(2) -0.001(2) 0.004(2) C8B 0.021(3) 0.049(3) 0.036(2) 0.026(2) 0.001(2) 0.013(2) C9B 0.023(3) 0.036(2) 0.033(2) 0.0184(19) 0.0014(18) 0.0069(19) C10B 0.023(3) 0.042(3) 0.037(2) 0.018(2) 0.0056(19) 0.009(2) C11B 0.031(3) 0.036(3) 0.041(2) 0.017(2) 0.005(2) 0.012(2) C12B 0.030(3) 0.043(3) 0.032(2) 0.021(2) -0.0054(19) 0.006(2) C13B 0.022(3) 0.044(3) 0.041(2) 0.020(2) 0.0029(19) 0.007(2) C14B 0.029(3) 0.035(2) 0.038(2) 0.015(2) 0.000(2) 0.010(2) C15B 0.030(3) 0.041(3) 0.052(3) 0.028(2) -0.001(2) 0.004(2) C16B 0.052(4) 0.039(3) 0.072(3) 0.016(3) 0.006(3) 0.006(2) C17B 0.046(4) 0.074(4) 0.107(4) 0.068(3) -0.022(3) -0.007(3) C18B 0.032(3) 0.053(3) 0.059(3) 0.028(2) 0.000(2) 0.000(2) O1C 0.028(2) 0.0558(19) 0.0576(19) 0.0366(16) -0.0077(15) 0.0032(15) O2C 0.076(3) 0.094(3) 0.076(3) 0.063(2) 0.022(2) 0.023(2) O3C 0.139(5) 0.124(4) 0.111(3) 0.072(3) -0.004(3) -0.069(4) N1C 0.061(3) 0.058(3) 0.085(3) 0.047(3) 0.022(3) 0.011(2) N2C 0.024(2) 0.044(2) 0.039(2) 0.0225(17) 0.0016(16) 0.0067(16) C1C 0.033(3) 0.049(3) 0.063(3) 0.038(3) 0.017(2) 0.014(2) C2C 0.035(3) 0.048(3) 0.061(3) 0.030(3) 0.002(2) 0.010(2) C3C 0.033(3) 0.042(3) 0.046(3) 0.027(2) 0.003(2) 0.008(2) C4C 0.029(3) 0.036(2) 0.046(3) 0.026(2) 0.010(2) 0.012(2) C5C 0.019(2) 0.040(3) 0.046(3) 0.024(2) 0.006(2) 0.0114(19) C6C 0.036(3) 0.048(3) 0.055(3) 0.033(2) 0.016(2) 0.021(2) C7C 0.034(3) 0.053(3) 0.043(3) 0.026(2) 0.005(2) 0.008(2) C8C 0.024(3) 0.040(3) 0.034(2) 0.016(2) 0.007(2) 0.015(2) C9C 0.018(2) 0.038(2) 0.041(3) 0.023(2) 0.0034(19) 0.0123(19) C10C 0.029(3) 0.039(3) 0.040(3) 0.018(2) 0.002(2) 0.012(2) C11C 0.035(3) 0.043(3) 0.032(2) 0.018(2) 0.003(2) 0.014(2) C12C 0.025(3) 0.037(2) 0.040(2) 0.024(2) 0.009(2) 0.017(2) C13C 0.037(3) 0.033(2) 0.035(3) 0.009(2) -0.003(2) 0.011(2) C14C 0.030(3) 0.039(2) 0.037(2) 0.023(2) 0.009(2) 0.013(2) C15C 0.025(3) 0.039(2) 0.044(2) 0.025(2) 0.004(2) 0.009(2) C16C 0.037(3) 0.073(3) 0.069(3) 0.052(3) 0.012(2) 0.016(2) C17C 0.041(3) 0.041(3) 0.067(3) 0.027(2) 0.015(2) 0.009(2) C18C 0.036(3) 0.056(3) 0.044(3) 0.024(2) 0.011(2) 0.019(2) C50 0.231(13) 0.137(8) 0.229(12) 0.047(9) -0.039(9) 0.098(9) Cl1S 0.0932(16) 0.1192(16) 0.1370(17) 0.0405(15) -0.0398(13) 0.0221(13) _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 O1 C8 1.230(5) . ? O2 N1 1.228(4) . ? O3 N1 1.209(4) . ? N1 C1 1.465(5) . ? N2 C8 1.386(5) . ? N2 C4 1.409(5) . ? C1 C2 1.379(5) . ? C1 C6 1.406(5) . ? C2 C3 1.376(5) . ? C3 C4 1.401(5) . ? C4 C5 1.418(5) . ? C5 C6 1.393(5) . ? C5 C7 1.488(5) . ? C8 C9 1.485(5) . ? C9 C14 1.388(5) . ? C9 C10 1.406(5) . ? C10 C11 1.370(5) . ? C11 C12 1.399(5) . ? C12 C13 1.401(5) . ? C12 C15 1.522(5) . ? C13 C14 1.379(5) . ? C15 C18 1.534(5) . ? C15 C16 1.540(5) . ? C15 C17 1.549(5) . ? O1B C8B 1.224(4) . ? O2B N1B 1.226(4) . ? O3B N1B 1.217(4) . ? N1B C1B 1.466(5) . ? N2B C8B 1.382(5) . ? N2B C4B 1.406(4) . ? C1B C6B 1.370(5) . ? C1B C2B 1.374(5) . ? C2B C3B 1.374(5) . ? C3B C4B 1.383(5) . ? C4B C5B 1.410(5) . ? C5B C6B 1.383(5) . ? C5B C7B 1.504(5) . ? C8B C9B 1.473(5) . ? C9B C10B 1.391(5) . ? C9B C14B 1.407(5) . ? C10B C11B 1.370(5) . ? C11B C12B 1.404(5) . ? C12B C13B 1.404(5) . ? C12B C15B 1.525(5) . ? C13B C14B 1.377(5) . ? C15B C18B 1.506(6) . ? C15B C17B 1.543(6) . ? C15B C16B 1.549(6) . ? O1C C8C 1.225(4) . ? O2C N1C 1.218(5) . ? O3C N1C 1.228(5) . ? N1C C1C 1.478(5) . ? N2C C8C 1.379(5) . ? N2C C4C 1.409(5) . ? C1C C6C 1.371(6) . ? C1C C2C 1.394(6) . ? C2C C3C 1.369(5) . ? C3C C4C 1.391(5) . ? C4C C5C 1.421(5) . ? C5C C6C 1.394(5) . ? C5C C7C 1.507(5) . ? C8C C9C 1.464(5) . ? C9C C14C 1.388(5) . ? C9C C10C 1.391(5) . ? C10C C11C 1.395(5) . ? C11C C12C 1.389(5) . ? C12C C13C 1.409(5) . ? C12C C15C 1.521(5) . ? C13C C14C 1.387(5) . ? C15C C17C 1.526(5) . ? C15C C16C 1.539(5) . ? C15C C18C 1.551(5) . ? C50 Cl1S 1.761(12) . ? C50 Cl1S 1.793(14) 2_656 ? C50 C50 1.951(17) 2_656 ? Cl1S C50 1.793(14) 2_656 ? 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 O3 N1 O2 122.9(4) . . ? O3 N1 C1 118.5(4) . . ? O2 N1 C1 118.7(4) . . ? C8 N2 C4 125.9(3) . . ? C2 C1 C6 120.8(4) . . ? C2 C1 N1 119.8(4) . . ? C6 C1 N1 119.4(4) . . ? C3 C2 C1 119.2(4) . . ? C2 C3 C4 121.0(4) . . ? C3 C4 N2 121.8(4) . . ? C3 C4 C5 120.5(4) . . ? N2 C4 C5 117.6(3) . . ? C6 C5 C4 117.4(4) . . ? C6 C5 C7 120.7(4) . . ? C4 C5 C7 121.9(4) . . ? C5 C6 C1 121.1(4) . . ? O1 C8 N2 121.4(4) . . ? O1 C8 C9 122.7(4) . . ? N2 C8 C9 115.9(4) . . ? C14 C9 C10 116.9(4) . . ? C14 C9 C8 125.0(4) . . ? C10 C9 C8 118.2(4) . . ? C11 C10 C9 121.2(4) . . ? C10 C11 C12 122.6(4) . . ? C11 C12 C13 115.4(4) . . ? C11 C12 C15 122.1(4) . . ? C13 C12 C15 122.4(4) . . ? C14 C13 C12 122.5(4) . . ? C13 C14 C9 121.3(4) . . ? C12 C15 C18 112.7(3) . . ? C12 C15 C16 109.7(3) . . ? C18 C15 C16 109.0(4) . . ? C12 C15 C17 109.1(3) . . ? C18 C15 C17 107.3(3) . . ? C16 C15 C17 108.9(3) . . ? O3B N1B O2B 123.8(4) . . ? O3B N1B C1B 118.1(4) . . ? O2B N1B C1B 118.2(4) . . ? C8B N2B C4B 122.4(3) . . ? C6B C1B C2B 121.3(4) . . ? C6B C1B N1B 119.4(4) . . ? C2B C1B N1B 119.3(4) . . ? C3B C2B C1B 118.0(4) . . ? C2B C3B C4B 121.8(4) . . ? C3B C4B N2B 120.2(3) . . ? C3B C4B C5B 119.8(3) . . ? N2B C4B C5B 119.9(3) . . ? C6B C5B C4B 117.2(3) . . ? C6B C5B C7B 121.3(4) . . ? C4B C5B C7B 121.5(4) . . ? C1B C6B C5B 121.7(4) . . ? O1B C8B N2B 121.4(4) . . ? O1B C8B C9B 120.4(4) . . ? N2B C8B C9B 118.2(4) . . ? C10B C9B C14B 116.9(4) . . ? C10B C9B C8B 118.8(4) . . ? C14B C9B C8B 124.3(4) . . ? C11B C10B C9B 121.5(4) . . ? C10B C11B C12B 122.4(4) . . ? C13B C12B C11B 116.1(4) . . ? C13B C12B C15B 122.5(4) . . ? C11B C12B C15B 121.2(4) . . ? C14B C13B C12B 121.6(4) . . ? C13B C14B C9B 121.5(4) . . ? C18B C15B C12B 112.6(4) . . ? C18B C15B C17B 108.3(4) . . ? C12B C15B C17B 107.7(3) . . ? C18B C15B C16B 106.7(4) . . ? C12B C15B C16B 111.0(3) . . ? C17B C15B C16B 110.5(4) . . ? O2C N1C O3C 123.4(4) . . ? O2C N1C C1C 119.1(5) . . ? O3C N1C C1C 117.3(5) . . ? C8C N2C C4C 126.0(4) . . ? C6C C1C C2C 122.6(4) . . ? C6C C1C N1C 118.7(4) . . ? C2C C1C N1C 118.7(4) . . ? C3C C2C C1C 117.6(4) . . ? C2C C3C C4C 122.3(4) . . ? C3C C4C N2C 123.0(4) . . ? C3C C4C C5C 119.0(4) . . ? N2C C4C C5C 118.0(3) . . ? C6C C5C C4C 118.8(4) . . ? C6C C5C C7C 120.3(4) . . ? C4C C5C C7C 120.9(3) . . ? C1C C6C C5C 119.7(4) . . ? O1C C8C N2C 121.9(4) . . ? O1C C8C C9C 122.0(4) . . ? N2C C8C C9C 116.1(4) . . ? C14C C9C C10C 117.7(4) . . ? C14C C9C C8C 123.9(4) . . ? C10C C9C C8C 118.4(4) . . ? C9C C10C C11C 120.6(4) . . ? C12C C11C C10C 122.5(4) . . ? C11C C12C C13C 115.8(4) . . ? C11C C12C C15C 121.1(3) . . ? C13C C12C C15C 123.0(4) . . ? C14C C13C C12C 121.8(4) . . ? C13C C14C C9C 121.3(4) . . ? C12C C15C C17C 112.8(3) . . ? C12C C15C C16C 110.1(3) . . ? C17C C15C C16C 109.0(3) . . ? C12C C15C C18C 109.0(3) . . ? C17C C15C C18C 106.6(3) . . ? C16C C15C C18C 109.2(3) . . ? Cl1S C50 Cl1S 113.4(5) . 2_656 ? Cl1S C50 C50 57.5(6) . 2_656 ? Cl1S C50 C50 55.9(7) 2_656 2_656 ? C50 Cl1S C50 66.6(5) . 2_656 ? 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 O3 N1 C1 C2 10.1(6) . . . . ? O2 N1 C1 C2 -169.1(4) . . . . ? O3 N1 C1 C6 -170.7(4) . . . . ? O2 N1 C1 C6 10.1(6) . . . . ? C6 C1 C2 C3 -0.4(6) . . . . ? N1 C1 C2 C3 178.7(4) . . . . ? C1 C2 C3 C4 -0.1(6) . . . . ? C2 C3 C4 N2 176.8(4) . . . . ? C2 C3 C4 C5 0.2(6) . . . . ? C8 N2 C4 C3 38.6(6) . . . . ? C8 N2 C4 C5 -144.7(4) . . . . ? C3 C4 C5 C6 0.2(6) . . . . ? N2 C4 C5 C6 -176.5(3) . . . . ? C3 C4 C5 C7 -177.3(4) . . . . ? N2 C4 C5 C7 5.9(6) . . . . ? C4 C5 C6 C1 -0.8(6) . . . . ? C7 C5 C6 C1 176.8(4) . . . . ? C2 C1 C6 C5 0.9(6) . . . . ? N1 C1 C6 C5 -178.3(4) . . . . ? C4 N2 C8 O1 2.4(6) . . . . ? C4 N2 C8 C9 -176.1(3) . . . . ? O1 C8 C9 C14 175.7(4) . . . . ? N2 C8 C9 C14 -5.8(6) . . . . ? O1 C8 C9 C10 -5.3(6) . . . . ? N2 C8 C9 C10 173.2(3) . . . . ? C14 C9 C10 C11 2.1(6) . . . . ? C8 C9 C10 C11 -177.0(4) . . . . ? C9 C10 C11 C12 0.1(6) . . . . ? C10 C11 C12 C13 -1.9(6) . . . . ? C10 C11 C12 C15 177.9(4) . . . . ? C11 C12 C13 C14 1.4(6) . . . . ? C15 C12 C13 C14 -178.3(4) . . . . ? C12 C13 C14 C9 0.7(7) . . . . ? C10 C9 C14 C13 -2.5(6) . . . . ? C8 C9 C14 C13 176.5(4) . . . . ? C11 C12 C15 C18 -174.5(4) . . . . ? C13 C12 C15 C18 5.3(5) . . . . ? C11 C12 C15 C16 -52.8(5) . . . . ? C13 C12 C15 C16 127.0(4) . . . . ? C11 C12 C15 C17 66.4(5) . . . . ? C13 C12 C15 C17 -113.8(4) . . . . ? O3B N1B C1B C6B -171.2(4) . . . . ? O2B N1B C1B C6B 9.1(6) . . . . ? O3B N1B C1B C2B 11.1(6) . . . . ? O2B N1B C1B C2B -168.6(4) . . . . ? C6B C1B C2B C3B -2.3(6) . . . . ? N1B C1B C2B C3B 175.3(4) . . . . ? C1B C2B C3B C4B -1.3(6) . . . . ? C2B C3B C4B N2B -172.4(4) . . . . ? C2B C3B C4B C5B 5.1(6) . . . . ? C8B N2B C4B C3B 47.9(5) . . . . ? C8B N2B C4B C5B -129.6(4) . . . . ? C3B C4B C5B C6B -5.1(6) . . . . ? N2B C4B C5B C6B 172.4(3) . . . . ? C3B C4B C5B C7B 176.2(4) . . . . ? N2B C4B C5B C7B -6.3(6) . . . . ? C2B C1B C6B C5B 2.2(6) . . . . ? N1B C1B C6B C5B -175.5(4) . . . . ? C4B C5B C6B C1B 1.6(6) . . . . ? C7B C5B C6B C1B -179.7(4) . . . . ? C4B N2B C8B O1B -2.5(6) . . . . ? C4B N2B C8B C9B 175.3(3) . . . . ? O1B C8B C9B C10B 22.3(6) . . . . ? N2B C8B C9B C10B -155.5(3) . . . . ? O1B C8B C9B C14B -157.6(4) . . . . ? N2B C8B C9B C14B 24.6(5) . . . . ? C14B C9B C10B C11B -1.3(6) . . . . ? C8B C9B C10B C11B 178.8(4) . . . . ? C9B C10B C11B C12B 0.8(6) . . . . ? C10B C11B C12B C13B 0.5(6) . . . . ? C10B C11B C12B C15B -174.0(4) . . . . ? C11B C12B C13B C14B -1.2(6) . . . . ? C15B C12B C13B C14B 173.3(4) . . . . ? C12B C13B C14B C9B 0.6(6) . . . . ? C10B C9B C14B C13B 0.6(6) . . . . ? C8B C9B C14B C13B -179.5(4) . . . . ? C13B C12B C15B C18B 20.5(5) . . . . ? C11B C12B C15B C18B -165.3(4) . . . . ? C13B C12B C15B C17B -98.8(5) . . . . ? C11B C12B C15B C17B 75.4(5) . . . . ? C13B C12B C15B C16B 140.2(4) . . . . ? C11B C12B C15B C16B -45.7(5) . . . . ? O2C N1C C1C C6C 13.5(6) . . . . ? O3C N1C C1C C6C -163.1(5) . . . . ? O2C N1C C1C C2C -166.5(4) . . . . ? O3C N1C C1C C2C 16.9(7) . . . . ? C6C C1C C2C C3C -1.1(7) . . . . ? N1C C1C C2C C3C 178.8(4) . . . . ? C1C C2C C3C C4C 2.2(6) . . . . ? C2C C3C C4C N2C 179.2(4) . . . . ? C2C C3C C4C C5C -1.6(6) . . . . ? C8C N2C C4C C3C -28.0(6) . . . . ? C8C N2C C4C C5C 152.8(4) . . . . ? C3C C4C C5C C6C -0.1(6) . . . . ? N2C C4C C5C C6C 179.2(4) . . . . ? C3C C4C C5C C7C -179.9(4) . . . . ? N2C C4C C5C C7C -0.7(6) . . . . ? C2C C1C C6C C5C -0.5(7) . . . . ? N1C C1C C6C C5C 179.6(4) . . . . ? C4C C5C C6C C1C 1.1(6) . . . . ? C7C C5C C6C C1C -179.1(4) . . . . ? C4C N2C C8C O1C 2.7(6) . . . . ? C4C N2C C8C C9C -176.3(3) . . . . ? O1C C8C C9C C14C -150.3(4) . . . . ? N2C C8C C9C C14C 28.8(6) . . . . ? O1C C8C C9C C10C 30.0(6) . . . . ? N2C C8C C9C C10C -151.0(4) . . . . ? C14C C9C C10C C11C -5.0(6) . . . . ? C8C C9C C10C C11C 174.7(4) . . . . ? C9C C10C C11C C12C 0.7(6) . . . . ? C10C C11C C12C C13C 4.2(6) . . . . ? C10C C11C C12C C15C -174.0(4) . . . . ? C11C C12C C13C C14C -4.7(6) . . . . ? C15C C12C C13C C14C 173.4(4) . . . . ? C12C C13C C14C C9C 0.5(6) . . . . ? C10C C9C C14C C13C 4.5(6) . . . . ? C8C C9C C14C C13C -175.3(4) . . . . ? C11C C12C C15C C17C 169.6(4) . . . . ? C13C C12C C15C C17C -8.4(5) . . . . ? C11C C12C C15C C16C -68.4(5) . . . . ? C13C C12C C15C C16C 113.6(4) . . . . ? C11C C12C C15C C18C 51.4(5) . . . . ? C13C C12C C15C C18C -126.6(4) . . . . ? Cl1S C50 Cl1S C50 0.0 2_656 . . 2_656 ? _diffrn_measured_fraction_theta_max 0.922 _diffrn_reflns_theta_full 28.46 _diffrn_measured_fraction_theta_full 0.922 _refine_diff_density_max 0.389 _refine_diff_density_min -0.444 _refine_diff_density_rms 0.080 data_gah13 _database_code_CSD 158583 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H22 N2 O3' _chemical_formula_weight 326.39 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)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 10.818(4) _cell_length_b 26.351(8) _cell_length_c 19.810(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.08(3) _cell_angle_gamma 90.00 _cell_volume 5647(3) _cell_formula_units_Z 12 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.45 _exptl_crystal_size_min 0.45 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.152 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2088 _exptl_absorpt_coefficient_mu 0.078 _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 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 7408 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.1192 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 28 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.86 _diffrn_reflns_theta_max 22.52 _reflns_number_total 7408 _reflns_number_gt 2737 _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^)+(0.1465P)^2^+3.5223P] 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 7408 _refine_ls_number_parameters 709 _refine_ls_number_restraints 60 _refine_ls_R_factor_all 0.2435 _refine_ls_R_factor_gt 0.1042 _refine_ls_wR_factor_ref 0.3433 _refine_ls_wR_factor_gt 0.2554 _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_restrained_S_all 1.020 _refine_ls_shift/su_max 0.005 _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 O1A O 0.8492(7) -0.0041(4) 0.5412(3) 0.142(3) Uani 1 1 d . . . O2A O 0.6580(7) 0.0180(3) 0.5430(3) 0.109(2) Uani 1 1 d . . . O3A O 0.8229(7) 0.0647(3) 0.2065(3) 0.130(3) Uani 1 1 d . . . N1A N 0.7508(9) 0.0054(3) 0.5125(3) 0.092(2) Uani 1 1 d . . . N2A N 0.7341(6) -0.0102(2) 0.2290(3) 0.0772(19) Uani 1 1 d . . . H2AA H 0.7003 -0.0386 0.2117 0.080 Uiso 1 1 d R . . C1A C 0.7456(9) 0.0029(3) 0.4387(4) 0.077(2) Uani 1 1 d . . . C2A C 0.8541(9) -0.0046(3) 0.4043(4) 0.085(3) Uani 1 1 d . . . H2AB H 0.9300 -0.0086 0.4288 0.080 Uiso 1 1 d R . . C3A C 0.8534(8) -0.0089(3) 0.3338(4) 0.076(2) Uani 1 1 d . . . C4A C 0.7381(9) -0.0048(3) 0.3009(4) 0.072(2) Uani 1 1 d . . . C5A C 0.6294(8) 0.0033(3) 0.3368(4) 0.076(2) Uani 1 1 d . . . C6A C 0.6338(8) 0.0070(3) 0.4063(4) 0.074(2) Uani 1 1 d . . . H6AA H 0.5590 0.0119 0.4315 0.080 Uiso 1 1 d R . . C7A C 0.7772(9) 0.0248(4) 0.1859(4) 0.086(3) Uani 1 1 d . . . C8A C 0.7677(8) 0.0146(3) 0.1134(4) 0.076(2) Uani 1 1 d . . . C9A C 0.7855(10) -0.0322(4) 0.0871(5) 0.123(4) Uani 1 1 d . . . H9AA H 0.7982 -0.0601 0.1174 0.080 Uiso 1 1 d R . . C10A C 0.7879(11) -0.0407(5) 0.0164(5) 0.131(4) Uani 1 1 d . . . H10A H 0.8074 -0.0735 -0.0019 0.080 Uiso 1 1 d R . . C11A C 0.7591(9) -0.0019(4) -0.0286(4) 0.085(3) Uani 1 1 d . A . C12A C 0.7378(12) 0.0423(5) -0.0007(5) 0.141(5) Uani 1 1 d . . . H12A H 0.7228 0.0703 -0.0306 0.080 Uiso 1 1 d R . . C13A C 0.7381(11) 0.0502(4) 0.0688(5) 0.130(4) Uani 1 1 d . . . H13A H 0.7221 0.0836 0.0860 0.080 Uiso 1 1 d R . . C14A C 0.5081(8) 0.0077(4) 0.3003(4) 0.104(3) Uani 1 1 d . . . H14A H 0.5234 0.0048 0.2527 0.080 Uiso 1 1 d R . . H14B H 0.4539 -0.0191 0.3144 0.080 Uiso 1 1 d R . . H14C H 0.4704 0.0399 0.3096 0.080 Uiso 1 1 d R . . C15A C 0.9720(9) -0.0184(4) 0.2966(4) 0.118(3) Uani 1 1 d . . . H15A H 0.9548 -0.0193 0.2491 0.080 Uiso 1 1 d R . . H15B H 1.0299 0.0083 0.3060 0.080 Uiso 1 1 d R . . H15C H 1.0067 -0.0503 0.3104 0.080 Uiso 1 1 d R . . C16A C 0.7555(11) -0.0103(5) -0.1038(5) 0.115(4) Uani 1 1 d D . . C17A C 0.669(5) -0.0515(17) -0.1296(18) 0.181(7) Uani 0.316(16) 1 d PDU A 1 H17A H 0.5813 -0.0493 -0.1248 0.271 Uiso 0.316(16) 1 d PR A 1 H17B H 0.7006 -0.0779 -0.1009 0.271 Uiso 0.316(16) 1 d PR A 1 H17C H 0.6897 -0.0590 -0.1757 0.271 Uiso 0.316(16) 1 d PR A 1 C17X C 0.6172(18) -0.0163(10) -0.1211(8) 0.180(7) Uani 0.684(16) 1 d PDU A 2 H17D H 0.5744 0.0156 -0.1223 0.271 Uiso 0.684(16) 1 d PR A 2 H17E H 0.5796 -0.0380 -0.0879 0.271 Uiso 0.684(16) 1 d PR A 2 H17F H 0.6124 -0.0322 -0.1646 0.271 Uiso 0.684(16) 1 d PR A 2 C18A C 0.7810(16) 0.0338(5) -0.1462(6) 0.233(9) Uani 1 1 d . A . H18A H 0.8644 0.0449 -0.1389 0.080 Uiso 1 1 d R . . H18B H 0.7691 0.0265 -0.1933 0.080 Uiso 1 1 d R . . H18C H 0.7248 0.0601 -0.1327 0.080 Uiso 1 1 d R . . C19A C 0.888(3) -0.028(2) -0.1192(19) 0.181(7) Uani 0.316(16) 1 d PDU A 1 H19A H 0.9146 -0.0162 -0.1625 0.272 Uiso 0.316(16) 1 d PR A 1 H19B H 0.9002 -0.0644 -0.1168 0.272 Uiso 0.316(16) 1 d PR A 1 H19C H 0.9366 -0.0122 -0.0845 0.272 Uiso 0.316(16) 1 d PR A 1 C19X C 0.812(3) -0.0611(8) -0.1253(8) 0.181(7) Uani 0.684(16) 1 d PDU A 2 H19D H 0.7973 -0.0673 -0.1724 0.272 Uiso 0.684(16) 1 d PR A 2 H19E H 0.7850 -0.0899 -0.0995 0.272 Uiso 0.684(16) 1 d PR A 2 H19F H 0.8985 -0.0556 -0.1179 0.272 Uiso 0.684(16) 1 d PR A 2 O1B O 0.5587(7) 0.1216(3) 0.4723(3) 0.114(2) Uani 1 1 d . . . O2B O 0.3683(7) 0.1004(3) 0.4796(3) 0.122(3) Uani 1 1 d . . . O3B O 0.4258(6) 0.0913(2) 0.8245(3) 0.105(2) Uani 1 1 d . . . N1B N 0.4645(9) 0.1151(3) 0.5050(3) 0.085(2) Uani 1 1 d . . . N2B N 0.4781(6) 0.1669(2) 0.7801(3) 0.0749(19) Uani 1 1 d . . . H2BA H 0.5017 0.1991 0.7883 0.080 Uiso 1 1 d R . . C1B C 0.4666(9) 0.1243(3) 0.5789(4) 0.072(2) Uani 1 1 d . . . C2B C 0.5802(8) 0.1294(3) 0.6096(4) 0.080(2) Uani 1 1 d . . . H2BB H 0.6560 0.1245 0.5853 0.080 Uiso 1 1 d R . . C3B C 0.5848(9) 0.1415(3) 0.6782(4) 0.076(2) Uani 1 1 d . . . C4B C 0.4724(9) 0.1496(3) 0.7116(4) 0.072(2) Uani 1 1 d . . . C5B C 0.3577(9) 0.1432(3) 0.6803(4) 0.078(2) Uani 1 1 d . . . C6B C 0.3560(8) 0.1303(3) 0.6125(4) 0.078(2) Uani 1 1 d . . . H6BA H 0.2787 0.1258 0.5893 0.080 Uiso 1 1 d R . . C7B C 0.4553(8) 0.1356(4) 0.8329(4) 0.077(2) Uani 1 1 d . . . C8B C 0.4696(8) 0.1587(3) 0.9012(4) 0.077(2) Uani 1 1 d . . . C9B C 0.4678(11) 0.1265(4) 0.9557(4) 0.132(4) Uani 1 1 d . . . H9BA H 0.4568 0.0907 0.9488 0.080 Uiso 1 1 d R . . C10B C 0.4824(13) 0.1456(4) 1.0199(5) 0.160(6) Uani 1 1 d . . . H10B H 0.4794 0.1225 1.0574 0.080 Uiso 1 1 d R . . C11B C 0.4958(10) 0.1947(4) 1.0360(5) 0.103(3) Uani 1 1 d . B . C12B C 0.4868(10) 0.2076(4) 0.9160(5) 0.113(4) Uani 1 1 d . . . H12B H 0.4947 0.2311 0.8794 0.080 Uiso 1 1 d R . . C13B C 0.4986(11) 0.2245(4) 0.9814(5) 0.130(4) Uani 1 1 d . . . H13B H 0.5070 0.2602 0.9894 0.080 Uiso 1 1 d R . . C14B C 0.2378(8) 0.1517(4) 0.7170(4) 0.101(3) Uani 1 1 d . . . H14D H 0.2539 0.1602 0.7633 0.080 Uiso 1 1 d R . . H14E H 0.1946 0.1791 0.6956 0.080 Uiso 1 1 d R . . H14F H 0.1882 0.1215 0.7150 0.080 Uiso 1 1 d R . . C15B C 0.7065(8) 0.1469(4) 0.7145(4) 0.112(3) Uani 1 1 d . . . H15D H 0.6930 0.1555 0.7610 0.080 Uiso 1 1 d R . . H15E H 0.7522 0.1157 0.7119 0.080 Uiso 1 1 d R . . H15F H 0.7525 0.1735 0.6930 0.080 Uiso 1 1 d R . . C16B C 0.5080(15) 0.2147(5) 1.1075(6) 0.147(5) Uani 1 1 d D . . C17B C 0.514(2) 0.1753(6) 1.1574(6) 0.332(15) Uani 1 1 d . B . H17D H 0.4346 0.1588 1.1580 0.080 Uiso 1 1 d R . . H17E H 0.5765 0.1512 1.1458 0.080 Uiso 1 1 d R . . H17F H 0.5309 0.1892 1.2013 0.080 Uiso 1 1 d R . . C18B C 0.440(3) 0.2641(9) 1.1213(9) 0.171(11) Uani 0.70(2) 1 d PDU B 1 H18D H 0.3530 0.2587 1.1162 0.257 Uiso 0.70(2) 1 d PR B 1 H18E H 0.4671 0.2895 1.0898 0.257 Uiso 0.70(2) 1 d PR B 1 H18F H 0.4575 0.2753 1.1664 0.257 Uiso 0.70(2) 1 d PR B 1 C18Y C 0.372(3) 0.224(2) 1.131(2) 0.171(11) Uani 0.30(2) 1 d PDU B 2 H18G H 0.3329 0.1918 1.1397 0.257 Uiso 0.30(2) 1 d PR B 2 H18H H 0.3276 0.2413 1.0959 0.257 Uiso 0.30(2) 1 d PR B 2 H18I H 0.3721 0.2440 1.1712 0.257 Uiso 0.30(2) 1 d PR B 2 C19B C 0.648(2) 0.2288(12) 1.1195(15) 0.231(13) Uani 0.70(2) 1 d PDU B 1 H19G H 0.6584 0.2429 1.1637 0.346 Uiso 0.70(2) 1 d PR B 1 H19H H 0.6740 0.2530 1.0862 0.346 Uiso 0.70(2) 1 d PR B 1 H19I H 0.6969 0.1985 1.1154 0.346 Uiso 0.70(2) 1 d PR B 1 C19Y C 0.604(5) 0.2586(18) 1.108(4) 0.231(13) Uani 0.30(2) 1 d PDU B 2 H19J H 0.6801 0.2457 1.1253 0.347 Uiso 0.30(2) 1 d PR B 2 H19K H 0.5743 0.2855 1.1360 0.347 Uiso 0.30(2) 1 d PR B 2 H19L H 0.6169 0.2713 1.0628 0.347 Uiso 0.30(2) 1 d PR B 2 O1C O 0.5653(7) 0.3805(3) 1.0603(3) 0.127(3) Uani 1 1 d . . . O2C O 0.3725(8) 0.3846(4) 1.0584(4) 0.162(4) Uani 1 1 d . . . O3C O 0.5465(7) 0.2707(2) 0.7514(3) 0.108(2) Uani 1 1 d . . . N1C N 0.4687(9) 0.3792(3) 1.0304(4) 0.102(3) Uani 1 1 d . . . N2C N 0.4669(6) 0.3490(3) 0.7493(3) 0.080(2) Uani 1 1 d . . . H2CA H 0.4392 0.3743 0.7228 0.080 Uiso 1 1 d R . . C1C C 0.4676(10) 0.3709(3) 0.9568(4) 0.083(3) Uani 1 1 d . . . C2C C 0.5784(9) 0.3717(3) 0.9240(4) 0.084(3) Uani 1 1 d . . . H2CB H 0.6540 0.3768 0.9485 0.080 Uiso 1 1 d R . . C3C C 0.5806(9) 0.3636(3) 0.8540(4) 0.080(2) Uani 1 1 d . . . C4C C 0.4672(9) 0.3563(3) 0.8216(4) 0.071(2) Uani 1 1 d . . . C5C C 0.3537(9) 0.3563(3) 0.8556(4) 0.076(2) Uani 1 1 d . . . C6C C 0.3564(9) 0.3639(3) 0.9247(4) 0.082(2) Uani 1 1 d . . . H6CA H 0.2807 0.3645 0.9499 0.080 Uiso 1 1 d R . . C7C C 0.5047(8) 0.3060(3) 0.7183(4) 0.078(2) Uani 1 1 d . . . C8C C 0.4967(9) 0.3053(3) 0.6440(4) 0.077(2) Uani 1 1 d . . . C9C C 0.5418(11) 0.2653(4) 0.6090(5) 0.129(4) Uani 1 1 d . . . H9CA H 0.5826 0.2392 0.6343 0.080 Uiso 1 1 d R . . C10C C 0.5381(12) 0.2616(4) 0.5390(5) 0.132(4) Uani 1 1 d . . . H10C H 0.5754 0.2331 0.5167 0.080 Uiso 1 1 d R . . C11C C 0.4883(10) 0.2983(4) 0.5000(4) 0.095(3) Uani 1 1 d . C . C12C C 0.4478(11) 0.3380(4) 0.5350(5) 0.139(5) Uani 1 1 d . . . H12C H 0.4172 0.3658 0.5086 0.080 Uiso 1 1 d R . . C13C C 0.4515(11) 0.3420(4) 0.6050(4) 0.122(4) Uani 1 1 d . . . H13C H 0.4244 0.3727 0.6266 0.080 Uiso 1 1 d R . . C14C C 0.2345(8) 0.3482(4) 0.8183(4) 0.108(3) Uani 1 1 d . . . H14G H 0.2531 0.3431 0.7714 0.080 Uiso 1 1 d R . . H14H H 0.1916 0.3190 0.8354 0.080 Uiso 1 1 d R . . H14I H 0.1834 0.3777 0.8233 0.080 Uiso 1 1 d R . . C15C C 0.6987(9) 0.3655(4) 0.8162(4) 0.122(4) Uani 1 1 d . . . H15G H 0.6811 0.3599 0.7693 0.080 Uiso 1 1 d R . . H15H H 0.7383 0.3979 0.8215 0.080 Uiso 1 1 d R . . H15I H 0.7525 0.3393 0.8325 0.080 Uiso 1 1 d R . . C16C C 0.4828(14) 0.2928(4) 0.4237(5) 0.128(4) Uani 1 1 d D . . C17C C 0.533(4) 0.3397(13) 0.394(2) 0.208(15) Uani 0.363(14) 1 d PDU C 1 H17G H 0.6101 0.3476 0.4154 0.311 Uiso 0.363(14) 1 d PR C 1 H17H H 0.4753 0.3669 0.4019 0.311 Uiso 0.363(14) 1 d PR C 1 H17I H 0.5448 0.3354 0.3467 0.311 Uiso 0.363(14) 1 d PR C 1 C17Z C 0.429(3) 0.3376(9) 0.3897(12) 0.208(15) Uani 0.637(14) 1 d PDU C 2 H17J H 0.4507 0.3677 0.4143 0.312 Uiso 0.637(14) 1 d PR C 2 H17K H 0.3410 0.3343 0.3878 0.312 Uiso 0.637(14) 1 d PR C 2 H17L H 0.4617 0.3399 0.3447 0.312 Uiso 0.637(14) 1 d PR C 2 C18C C 0.6017(19) 0.2742(11) 0.3969(7) 0.331(17) Uani 1 1 d D C 2 H18J H 0.5869 0.2519 0.3594 0.496 Uiso 1 1 d R C 2 H18K H 0.6449 0.2561 0.4318 0.496 Uiso 1 1 d R C 2 H18L H 0.6507 0.3025 0.3823 0.496 Uiso 1 1 d R C 2 C19C C 0.333(5) 0.2884(16) 0.4022(17) 0.181(10) Uani 0.363(14) 1 d PU C 1 H19M H 0.2874 0.3148 0.4241 0.271 Uiso 0.363(14) 1 d PR C 1 H19N H 0.3015 0.2559 0.4159 0.271 Uiso 0.363(14) 1 d PR C 1 H19O H 0.3255 0.2918 0.3542 0.271 Uiso 0.363(14) 1 d PR C 1 C19Z C 0.424(3) 0.2439(8) 0.4030(9) 0.181(10) Uani 0.637(14) 1 d PDU C 2 H19P H 0.4172 0.2426 0.3547 0.271 Uiso 0.637(14) 1 d PR C 2 H19Q H 0.3430 0.2416 0.4227 0.271 Uiso 0.637(14) 1 d PR C 2 H19R H 0.4737 0.2161 0.4185 0.271 Uiso 0.637(14) 1 d PR C 2 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 O1A 0.092(6) 0.267(10) 0.067(4) -0.005(5) -0.025(4) -0.001(6) O2A 0.109(5) 0.157(6) 0.062(4) -0.017(4) 0.006(4) -0.004(5) O3A 0.211(8) 0.115(5) 0.065(4) 0.001(4) -0.014(4) -0.077(5) N1A 0.093(7) 0.130(7) 0.052(5) -0.016(4) 0.002(5) -0.013(6) N2A 0.102(6) 0.070(4) 0.060(4) -0.003(3) 0.001(4) -0.019(4) C1A 0.076(7) 0.092(6) 0.062(5) -0.008(4) 0.001(5) -0.018(5) C2A 0.076(7) 0.113(7) 0.065(6) 0.004(5) -0.011(5) -0.007(6) C3A 0.078(7) 0.092(6) 0.060(5) -0.001(4) 0.002(5) -0.013(5) C4A 0.095(7) 0.073(5) 0.047(5) 0.001(4) -0.007(5) -0.021(5) C5A 0.072(6) 0.092(6) 0.064(5) -0.001(5) -0.019(5) 0.003(5) C6A 0.062(6) 0.088(6) 0.072(6) -0.009(4) -0.007(5) -0.007(5) C7A 0.113(8) 0.084(6) 0.060(5) -0.002(5) -0.009(5) -0.026(6) C8A 0.106(7) 0.063(5) 0.059(5) -0.005(4) -0.009(5) -0.003(5) C9A 0.161(11) 0.127(9) 0.081(7) 0.013(7) 0.006(7) -0.004(8) C10A 0.168(12) 0.147(10) 0.078(7) -0.033(7) 0.005(7) 0.017(8) C11A 0.105(8) 0.101(7) 0.050(5) -0.005(5) -0.004(5) 0.002(6) C12A 0.217(14) 0.152(11) 0.053(6) 0.011(6) -0.016(7) -0.014(10) C13A 0.190(12) 0.118(8) 0.082(7) -0.006(6) -0.015(7) 0.028(8) C14A 0.099(8) 0.125(8) 0.087(6) -0.003(6) -0.009(6) -0.006(6) C15A 0.101(8) 0.175(10) 0.077(6) -0.014(6) 0.013(6) -0.006(8) C16A 0.113(9) 0.168(10) 0.063(6) -0.011(7) 0.020(6) 0.001(8) C17A 0.27(2) 0.192(15) 0.083(7) -0.053(9) -0.042(10) 0.045(13) C17X 0.27(2) 0.191(15) 0.083(7) -0.050(9) -0.044(10) 0.044(14) C18A 0.37(3) 0.244(17) 0.083(8) 0.031(10) 0.050(11) -0.021(18) C19A 0.27(2) 0.194(16) 0.082(7) -0.055(9) -0.039(11) 0.047(14) C19X 0.27(2) 0.193(15) 0.083(7) -0.055(9) -0.040(10) 0.047(13) O1B 0.104(6) 0.157(6) 0.082(4) -0.002(4) 0.013(4) -0.005(5) O2B 0.104(6) 0.189(7) 0.073(4) -0.020(4) -0.022(4) -0.015(5) O3B 0.167(7) 0.072(4) 0.075(4) 0.002(3) -0.017(4) -0.040(4) N1B 0.090(7) 0.107(6) 0.057(5) 0.000(4) -0.001(5) -0.002(5) N2B 0.102(6) 0.064(4) 0.059(4) -0.006(3) -0.004(4) -0.016(4) C1B 0.076(7) 0.079(6) 0.060(5) 0.001(4) -0.008(5) -0.005(5) C2B 0.069(7) 0.100(6) 0.069(6) -0.007(5) -0.004(5) -0.003(5) C3B 0.079(7) 0.081(6) 0.068(5) 0.003(4) -0.013(5) -0.004(5) C4B 0.091(7) 0.064(5) 0.060(5) 0.013(4) -0.009(5) -0.006(5) C5B 0.084(7) 0.086(6) 0.064(5) 0.009(4) -0.001(5) 0.006(5) C6B 0.063(6) 0.098(6) 0.073(6) 0.010(5) 0.002(5) 0.002(5) C7B 0.081(7) 0.082(6) 0.069(5) 0.004(5) -0.001(5) -0.007(5) C8B 0.102(7) 0.068(5) 0.060(5) -0.008(4) -0.020(5) -0.015(5) C9B 0.247(14) 0.086(7) 0.063(6) 0.002(5) -0.023(7) -0.040(8) C10B 0.314(19) 0.105(9) 0.060(6) 0.023(6) -0.033(8) -0.038(10) C11B 0.142(10) 0.083(7) 0.084(7) -0.014(6) -0.030(6) 0.000(7) C12B 0.185(11) 0.079(7) 0.074(6) -0.005(5) 0.000(6) -0.014(7) C13B 0.225(14) 0.072(7) 0.094(8) -0.017(6) -0.013(8) -0.007(8) C14B 0.082(7) 0.132(8) 0.090(6) 0.007(6) 0.013(6) 0.019(6) C15B 0.089(8) 0.155(9) 0.091(6) 0.004(6) -0.004(6) -0.014(7) C16B 0.205(15) 0.152(11) 0.085(8) -0.009(8) -0.040(9) 0.011(11) C17B 0.64(5) 0.24(2) 0.115(12) -0.103(15) -0.07(2) -0.04(3) C18B 0.23(3) 0.17(2) 0.120(12) -0.074(16) -0.010(13) 0.083(19) C18Y 0.23(3) 0.17(2) 0.120(12) -0.074(16) -0.010(14) 0.08(2) C19B 0.19(2) 0.29(3) 0.21(2) -0.14(3) -0.137(17) 0.09(2) C19Y 0.19(2) 0.29(3) 0.21(2) -0.14(3) -0.137(17) 0.09(2) O1C 0.094(5) 0.211(8) 0.076(4) -0.004(4) -0.016(4) -0.003(5) O2C 0.083(6) 0.311(12) 0.092(5) -0.033(6) -0.010(4) 0.029(7) O3C 0.174(7) 0.067(4) 0.084(4) 0.015(3) -0.013(4) 0.019(4) N1C 0.084(7) 0.150(7) 0.072(6) 0.010(5) -0.007(5) 0.009(6) N2C 0.101(6) 0.077(5) 0.062(4) 0.009(4) -0.004(4) 0.007(4) C1C 0.091(8) 0.092(6) 0.066(6) 0.007(5) -0.008(6) 0.001(6) C2C 0.071(7) 0.108(7) 0.072(6) 0.007(5) -0.014(5) -0.006(6) C3C 0.070(7) 0.101(6) 0.069(6) 0.009(5) -0.001(5) -0.003(5) C4C 0.084(7) 0.064(5) 0.066(5) 0.003(4) -0.007(5) 0.012(5) C5C 0.074(7) 0.083(6) 0.072(6) 0.007(4) -0.010(5) 0.006(5) C6C 0.074(7) 0.102(6) 0.071(6) 0.002(5) -0.004(5) -0.003(5) C7C 0.099(7) 0.063(6) 0.073(6) -0.003(5) -0.005(5) -0.007(5) C8C 0.103(7) 0.055(5) 0.072(6) 0.005(5) 0.005(5) 0.005(5) C9C 0.205(13) 0.098(8) 0.083(7) 0.016(6) 0.008(7) 0.045(8) C10C 0.234(14) 0.089(7) 0.074(7) -0.002(6) 0.027(7) 0.047(8) C11C 0.129(9) 0.092(7) 0.065(6) -0.003(6) 0.008(6) 0.013(7) C12C 0.217(14) 0.129(9) 0.070(6) 0.001(6) -0.007(7) 0.075(9) C13C 0.198(12) 0.099(7) 0.067(6) -0.016(6) -0.002(7) 0.045(8) C14C 0.088(7) 0.152(9) 0.085(6) 0.007(6) -0.011(6) -0.017(7) C15C 0.086(8) 0.195(11) 0.085(6) 0.015(7) -0.004(6) -0.023(8) C16C 0.204(14) 0.102(8) 0.076(7) -0.005(6) -0.001(8) 0.035(9) C17C 0.35(4) 0.199(16) 0.069(9) -0.020(10) -0.05(2) 0.16(3) C17Z 0.35(4) 0.199(16) 0.069(9) -0.020(10) -0.05(2) 0.16(3) C18C 0.36(3) 0.53(4) 0.105(11) 0.026(17) 0.077(15) 0.21(3) C19C 0.31(3) 0.134(17) 0.104(11) -0.039(13) -0.029(16) -0.034(18) C19Z 0.31(3) 0.133(16) 0.104(11) -0.039(12) -0.029(16) -0.034(18) _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 O1A N1A 1.232(9) . ? O2A N1A 1.218(8) . ? O3A C7A 1.231(9) . ? N1A C1A 1.466(10) . ? N2A C7A 1.340(9) . ? N2A C4A 1.432(8) . ? C1A C2A 1.371(10) . ? C1A C6A 1.373(10) . ? C2A C3A 1.402(10) . ? C3A C4A 1.411(11) . ? C3A C15A 1.501(10) . ? C4A C5A 1.391(10) . ? C5A C6A 1.382(10) . ? C5A C14A 1.501(11) . ? C7A C8A 1.464(10) . ? C8A C13A 1.327(11) . ? C8A C9A 1.353(11) . ? C9A C10A 1.418(12) . ? C10A C11A 1.391(13) . ? C11A C12A 1.309(13) . ? C11A C16A 1.507(11) . ? C12A C13A 1.392(12) . ? C16A C18A 1.460(14) . ? C16A C17A 1.519(18) . ? C16A C19X 1.532(14) . ? C16A C17X 1.543(15) . ? C16A C19A 1.546(19) . ? O1B N1B 1.220(8) . ? O2B N1B 1.218(8) . ? O3B C7B 1.222(9) . ? N1B C1B 1.483(10) . ? N2B C7B 1.355(9) . ? N2B C4B 1.432(9) . ? C1B C2B 1.378(10) . ? C1B C6B 1.379(10) . ? C2B C3B 1.397(10) . ? C3B C4B 1.401(10) . ? C3B C15B 1.506(11) . ? C4B C5B 1.396(11) . ? C5B C6B 1.386(10) . ? C5B C14B 1.505(10) . ? C7B C8B 1.491(10) . ? C8B C12B 1.333(10) . ? C8B C9B 1.375(10) . ? C9B C10B 1.377(11) . ? C10B C11B 1.340(12) . ? C11B C13B 1.336(12) . ? C11B C16B 1.517(13) . ? C12B C13B 1.375(11) . ? C16B C17B 1.435(17) . ? C16B C18B 1.518(14) . ? C16B C19Y 1.55(2) . ? C16B C18Y 1.561(19) . ? C16B C19B 1.576(16) . ? O1C N1C 1.201(9) . ? O2C N1C 1.188(9) . ? O3C C7C 1.224(9) . ? N1C C1C 1.476(10) . ? N2C C7C 1.352(9) . ? N2C C4C 1.446(9) . ? C1C C2C 1.364(11) . ? C1C C6C 1.371(11) . ? C2C C3C 1.402(10) . ? C3C C4C 1.397(11) . ? C3C C15C 1.483(11) . ? C4C C5C 1.401(10) . ? C5C C6C 1.384(10) . ? C5C C14C 1.501(11) . ? C7C C8C 1.476(10) . ? C8C C13C 1.329(11) . ? C8C C9C 1.352(11) . ? C9C C10C 1.390(11) . ? C10C C11C 1.350(12) . ? C11C C12C 1.329(12) . ? C11C C16C 1.519(12) . ? C12C C13C 1.392(11) . ? C16C C17C 1.469(18) . ? C16C C18C 1.476(13) . ? C16C C17Z 1.477(14) . ? C16C C19Z 1.495(14) . ? C16C C19C 1.68(5) . ? 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 O2A N1A O1A 122.6(7) . . ? O2A N1A C1A 118.5(9) . . ? O1A N1A C1A 118.9(9) . . ? C7A N2A C4A 123.7(6) . . ? C2A C1A C6A 122.2(8) . . ? C2A C1A N1A 118.1(9) . . ? C6A C1A N1A 119.6(9) . . ? C1A C2A C3A 120.2(8) . . ? C2A C3A C4A 117.2(8) . . ? C2A C3A C15A 119.9(8) . . ? C4A C3A C15A 122.8(7) . . ? C5A C4A C3A 121.6(7) . . ? C5A C4A N2A 120.0(8) . . ? C3A C4A N2A 118.5(8) . . ? C6A C5A C4A 119.5(8) . . ? C6A C5A C14A 120.2(9) . . ? C4A C5A C14A 120.3(7) . . ? C1A C6A C5A 119.2(8) . . ? O3A C7A N2A 121.1(7) . . ? O3A C7A C8A 120.6(8) . . ? N2A C7A C8A 118.4(8) . . ? C13A C8A C9A 114.9(8) . . ? C13A C8A C7A 122.8(8) . . ? C9A C8A C7A 122.3(8) . . ? C8A C9A C10A 121.8(10) . . ? C11A C10A C9A 120.7(10) . . ? C12A C11A C10A 115.1(9) . . ? C12A C11A C16A 122.8(10) . . ? C10A C11A C16A 122.1(10) . . ? C11A C12A C13A 123.3(11) . . ? C8A C13A C12A 123.6(10) . . ? C18A C16A C11A 116.7(10) . . ? C18A C16A C17A 119(2) . . ? C11A C16A C17A 116.9(17) . . ? C18A C16A C19X 117.3(13) . . ? C11A C16A C19X 113.2(11) . . ? C17A C16A C19X 62(2) . . ? C18A C16A C17X 98.0(13) . . ? C11A C16A C17X 105.0(9) . . ? C17A C16A C17X 42(2) . . ? C19X C16A C17X 103.5(13) . . ? C18A C16A C19A 87(2) . . ? C11A C16A C19A 102.5(16) . . ? C17A C16A C19A 106(3) . . ? C19X C16A C19A 46.0(18) . . ? C17X C16A C19A 145.8(18) . . ? O2B N1B O1B 122.6(8) . . ? O2B N1B C1B 118.1(8) . . ? O1B N1B C1B 119.2(8) . . ? C7B N2B C4B 122.0(6) . . ? C2B C1B C6B 123.4(7) . . ? C2B C1B N1B 117.7(8) . . ? C6B C1B N1B 118.9(8) . . ? C1B C2B C3B 118.9(8) . . ? C2B C3B C4B 117.7(8) . . ? C2B C3B C15B 121.0(9) . . ? C4B C3B C15B 121.3(8) . . ? C5B C4B C3B 122.9(7) . . ? C5B C4B N2B 119.8(8) . . ? C3B C4B N2B 117.3(8) . . ? C6B C5B C4B 118.1(8) . . ? C6B C5B C14B 119.7(9) . . ? C4B C5B C14B 122.2(8) . . ? C1B C6B C5B 119.0(8) . . ? O3B C7B N2B 121.6(7) . . ? O3B C7B C8B 122.6(8) . . ? N2B C7B C8B 115.8(8) . . ? C12B C8B C9B 115.2(8) . . ? C12B C8B C7B 127.4(8) . . ? C9B C8B C7B 117.4(8) . . ? C8B C9B C10B 119.8(9) . . ? C11B C10B C9B 125.8(9) . . ? C13B C11B C10B 112.2(9) . . ? C13B C11B C16B 123.3(10) . . ? C10B C11B C16B 124.5(10) . . ? C8B C12B C13B 122.2(9) . . ? C11B C13B C12B 124.7(9) . . ? C17B C16B C11B 113.3(11) . . ? C17B C16B C18B 121.0(15) . . ? C11B C16B C18B 115.2(11) . . ? C17B C16B C19Y 121(3) . . ? C11B C16B C19Y 109(3) . . ? C18B C16B C19Y 72(3) . . ? C17B C16B C18Y 87(2) . . ? C11B C16B C18Y 104.5(19) . . ? C18B C16B C18Y 50.2(19) . . ? C19Y C16B C18Y 121(3) . . ? C17B C16B C19B 91.5(16) . . ? C11B C16B C19B 107.7(14) . . ? C18B C16B C19B 103.6(16) . . ? C19Y C16B C19B 35(2) . . ? C18Y C16B C19B 146(2) . . ? O2C N1C O1C 122.0(9) . . ? O2C N1C C1C 118.2(9) . . ? O1C N1C C1C 119.8(9) . . ? C7C N2C C4C 124.1(6) . . ? C2C C1C C6C 123.5(8) . . ? C2C C1C N1C 117.5(9) . . ? C6C C1C N1C 118.9(9) . . ? C1C C2C C3C 119.0(8) . . ? C4C C3C C2C 117.3(8) . . ? C4C C3C C15C 121.9(8) . . ? C2C C3C C15C 120.7(9) . . ? C3C C4C C5C 123.3(7) . . ? C3C C4C N2C 118.4(8) . . ? C5C C4C N2C 118.3(8) . . ? C6C C5C C4C 117.2(8) . . ? C6C C5C C14C 121.7(9) . . ? C4C C5C C14C 121.1(8) . . ? C1C C6C C5C 119.6(9) . . ? O3C C7C N2C 120.4(7) . . ? O3C C7C C8C 123.1(8) . . ? N2C C7C C8C 116.5(8) . . ? C13C C8C C9C 113.7(8) . . ? C13C C8C C7C 126.3(8) . . ? C9C C8C C7C 120.0(8) . . ? C8C C9C C10C 123.8(9) . . ? C11C C10C C9C 122.1(9) . . ? C12C C11C C10C 113.3(8) . . ? C12C C11C C16C 125.6(10) . . ? C10C C11C C16C 121.1(9) . . ? C11C C12C C13C 124.8(10) . . ? C8C C13C C12C 122.2(9) . . ? C17C C16C C18C 79(2) . . ? C17C C16C C17Z 44.8(19) . . ? C18C C16C C17Z 116.2(18) . . ? C17C C16C C19Z 141(2) . . ? C18C C16C C19Z 89.2(14) . . ? C17Z C16C C19Z 113.4(17) . . ? C17C C16C C11C 108(2) . . ? C18C C16C C11C 111.0(11) . . ? C17Z C16C C11C 113.1(13) . . ? C19Z C16C C11C 111.8(11) . . ? C17C C16C C19C 108(2) . . ? C18C C16C C19C 136.5(16) . . ? C17Z C16C C19C 64.1(17) . . ? C19Z C16C C19C 57.2(14) . . ? C11C C16C C19C 107.2(15) . . ? 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 O2A N1A C1A C2A 171.4(8) . . . . ? O1A N1A C1A C2A -7.0(13) . . . . ? O2A N1A C1A C6A -9.8(12) . . . . ? O1A N1A C1A C6A 171.8(9) . . . . ? C6A C1A C2A C3A -0.8(13) . . . . ? N1A C1A C2A C3A 178.0(7) . . . . ? C1A C2A C3A C4A 0.6(12) . . . . ? C1A C2A C3A C15A -178.5(8) . . . . ? C2A C3A C4A C5A 0.1(12) . . . . ? C15A C3A C4A C5A 179.1(8) . . . . ? C2A C3A C4A N2A -178.6(7) . . . . ? C15A C3A C4A N2A 0.4(12) . . . . ? C7A N2A C4A C5A 109.2(9) . . . . ? C7A N2A C4A C3A -72.0(11) . . . . ? C3A C4A C5A C6A -0.6(12) . . . . ? N2A C4A C5A C6A 178.1(7) . . . . ? C3A C4A C5A C14A 179.9(8) . . . . ? N2A C4A C5A C14A -1.4(12) . . . . ? C2A C1A C6A C5A 0.3(13) . . . . ? N1A C1A C6A C5A -178.4(7) . . . . ? C4A C5A C6A C1A 0.4(12) . . . . ? C14A C5A C6A C1A 179.9(8) . . . . ? C4A N2A C7A O3A -0.5(15) . . . . ? C4A N2A C7A C8A 180.0(8) . . . . ? O3A C7A C8A C13A -39.3(15) . . . . ? N2A C7A C8A C13A 140.3(10) . . . . ? O3A C7A C8A C9A 142.4(11) . . . . ? N2A C7A C8A C9A -38.0(14) . . . . ? C13A C8A C9A C10A 7.8(16) . . . . ? C7A C8A C9A C10A -173.8(9) . . . . ? C8A C9A C10A C11A -6.8(17) . . . . ? C9A C10A C11A C12A 3.8(16) . . . . ? C9A C10A C11A C16A -177.3(10) . . . . ? C10A C11A C12A C13A -2.7(18) . . . . ? C16A C11A C12A C13A 178.5(11) . . . . ? C9A C8A C13A C12A -6.6(17) . . . . ? C7A C8A C13A C12A 175.0(10) . . . . ? C11A C12A C13A C8A 4(2) . . . . ? C12A C11A C16A C18A 26.1(17) . . . . ? C10A C11A C16A C18A -152.6(12) . . . . ? C12A C11A C16A C17A -125(3) . . . . ? C10A C11A C16A C17A 57(3) . . . . ? C12A C11A C16A C19X 166.7(17) . . . . ? C10A C11A C16A C19X -12(2) . . . . ? C12A C11A C16A C17X -81.1(17) . . . . ? C10A C11A C16A C17X 100.2(16) . . . . ? C12A C11A C16A C19A 120(2) . . . . ? C10A C11A C16A C19A -59(2) . . . . ? O2B N1B C1B C2B 165.4(8) . . . . ? O1B N1B C1B C2B -13.4(12) . . . . ? O2B N1B C1B C6B -18.4(11) . . . . ? O1B N1B C1B C6B 162.8(8) . . . . ? C6B C1B C2B C3B -0.4(13) . . . . ? N1B C1B C2B C3B 175.6(7) . . . . ? C1B C2B C3B C4B -2.2(12) . . . . ? C1B C2B C3B C15B 179.2(8) . . . . ? C2B C3B C4B C5B 3.8(12) . . . . ? C15B C3B C4B C5B -177.6(8) . . . . ? C2B C3B C4B N2B -174.0(7) . . . . ? C15B C3B C4B N2B 4.6(11) . . . . ? C7B N2B C4B C5B 77.7(10) . . . . ? C7B N2B C4B C3B -104.4(9) . . . . ? C3B C4B C5B C6B -2.7(12) . . . . ? N2B C4B C5B C6B 175.0(7) . . . . ? C3B C4B C5B C14B 179.6(8) . . . . ? N2B C4B C5B C14B -2.7(12) . . . . ? C2B C1B C6B C5B 1.5(12) . . . . ? N1B C1B C6B C5B -174.5(7) . . . . ? C4B C5B C6B C1B 0.0(12) . . . . ? C14B C5B C6B C1B 177.8(7) . . . . ? C4B N2B C7B O3B -1.8(13) . . . . ? C4B N2B C7B C8B 177.8(8) . . . . ? O3B C7B C8B C12B -171.4(10) . . . . ? N2B C7B C8B C12B 9.1(14) . . . . ? O3B C7B C8B C9B 10.2(14) . . . . ? N2B C7B C8B C9B -169.3(9) . . . . ? C12B C8B C9B C10B 0.5(17) . . . . ? C7B C8B C9B C10B 179.0(10) . . . . ? C8B C9B C10B C11B 2(2) . . . . ? C9B C10B C11B C13B -3(2) . . . . ? C9B C10B C11B C16B 178.1(13) . . . . ? C9B C8B C12B C13B -1.7(16) . . . . ? C7B C8B C12B C13B 179.9(10) . . . . ? C10B C11B C13B C12B 1.3(19) . . . . ? C16B C11B C13B C12B -179.4(12) . . . . ? C8B C12B C13B C11B 1(2) . . . . ? C13B C11B C16B C17B -174.6(15) . . . . ? C10B C11B C16B C17B 5(2) . . . . ? C13B C11B C16B C18B 40(2) . . . . ? C10B C11B C16B C18B -140.7(19) . . . . ? C13B C11B C16B C19Y -38(3) . . . . ? C10B C11B C16B C19Y 141(3) . . . . ? C13B C11B C16B C18Y 93(3) . . . . ? C10B C11B C16B C18Y -88(3) . . . . ? C13B C11B C16B C19B -75(2) . . . . ? C10B C11B C16B C19B 104(2) . . . . ? O2C N1C C1C C2C 171.2(10) . . . . ? O1C N1C C1C C2C -8.3(13) . . . . ? O2C N1C C1C C6C -7.6(14) . . . . ? O1C N1C C1C C6C 172.8(9) . . . . ? C6C C1C C2C C3C -1.6(14) . . . . ? N1C C1C C2C C3C 179.6(8) . . . . ? C1C C2C C3C C4C 1.3(12) . . . . ? C1C C2C C3C C15C 178.3(9) . . . . ? C2C C3C C4C C5C -0.5(12) . . . . ? C15C C3C C4C C5C -177.4(8) . . . . ? C2C C3C C4C N2C 178.7(7) . . . . ? C15C C3C C4C N2C 1.8(12) . . . . ? C7C N2C C4C C3C 73.3(10) . . . . ? C7C N2C C4C C5C -107.4(9) . . . . ? C3C C4C C5C C6C -0.2(12) . . . . ? N2C C4C C5C C6C -179.4(7) . . . . ? C3C C4C C5C C14C -179.9(8) . . . . ? N2C C4C C5C C14C 0.9(11) . . . . ? C2C C1C C6C C5C 1.0(14) . . . . ? N1C C1C C6C C5C 179.8(8) . . . . ? C4C C5C C6C C1C -0.1(12) . . . . ? C14C C5C C6C C1C 179.7(8) . . . . ? C4C N2C C7C O3C -2.6(13) . . . . ? C4C N2C C7C C8C 179.5(8) . . . . ? O3C C7C C8C C13C 179.3(10) . . . . ? N2C C7C C8C C13C -2.8(14) . . . . ? O3C C7C C8C C9C -3.1(15) . . . . ? N2C C7C C8C C9C 174.8(9) . . . . ? C13C C8C C9C C10C -2.0(17) . . . . ? C7C C8C C9C C10C -179.9(10) . . . . ? C8C C9C C10C C11C 0(2) . . . . ? C9C C10C C11C C12C 2.0(18) . . . . ? C9C C10C C11C C16C -178.6(11) . . . . ? C10C C11C C12C C13C -1.9(19) . . . . ? C16C C11C C12C C13C 178.8(12) . . . . ? C9C C8C C13C C12C 2.2(17) . . . . ? C7C C8C C13C C12C 179.9(10) . . . . ? C11C C12C C13C C8C 0(2) . . . . ? C12C C11C C16C C17C 49(3) . . . . ? C10C C11C C16C C17C -130(2) . . . . ? C12C C11C C16C C18C 134.2(17) . . . . ? C10C C11C C16C C18C -45.2(19) . . . . ? C12C C11C C16C C17Z 1(2) . . . . ? C10C C11C C16C C17Z -177.9(19) . . . . ? C12C C11C C16C C19Z -128.0(17) . . . . ? C10C C11C C16C C19Z 53(2) . . . . ? C12C C11C C16C C19C -67(2) . . . . ? C10C C11C C16C C19C 113.6(19) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 22.52 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.393 _refine_diff_density_min -0.288 _refine_diff_density_rms 0.058 data_gah14 _database_code_CSD 158584 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '4 nitro N-2,6 diethylphenyl 4 t-butylbenzamide' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H26 N2 O3' _chemical_formula_weight 354.44 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/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 10.601(2) _cell_length_b 20.517(5) _cell_length_c 27.623(6) _cell_angle_alpha 90.00 _cell_angle_beta 94.625(4) _cell_angle_gamma 90.00 _cell_volume 5989(2) _cell_formula_units_Z 12 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.179 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2280 _exptl_absorpt_coefficient_mu 0.079 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.9691 _exptl_absorpt_correction_T_max 0.9937 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku R-axis IIc' _diffrn_measurement_method 'Image plate scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14484 _diffrn_reflns_av_R_equivalents 0.1477 _diffrn_reflns_av_sigmaI/netI 0.1347 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.24 _diffrn_reflns_theta_max 20.99 _reflns_number_total 5417 _reflns_number_gt 3105 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _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^)+(0.1845P)^2^+2.3445P] 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 5417 _refine_ls_number_parameters 610 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1961 _refine_ls_R_factor_gt 0.1184 _refine_ls_wR_factor_ref 0.3630 _refine_ls_wR_factor_gt 0.3090 _refine_ls_goodness_of_fit_ref 1.105 _refine_ls_restrained_S_all 1.105 _refine_ls_shift/su_max 2.796 _refine_ls_shift/su_mean 0.076 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 O1 O 0.5349(10) -0.0201(4) 0.6152(5) 0.190(6) Uani 1 1 d . . . O2 O 0.3417(10) -0.0155(4) 0.6084(5) 0.179(5) Uani 1 1 d . . . O3 O 0.4375(6) 0.3159(3) 0.5913(2) 0.078(2) Uani 1 1 d . . . O4 O 0.3382(8) -0.0307(3) 0.4891(4) 0.142(4) Uani 1 1 d . . . O5 O 0.1431(9) -0.0243(3) 0.4959(4) 0.157(5) Uani 1 1 d . . . O6 O 0.1916(7) 0.2908(3) 0.4328(2) 0.091(2) Uani 1 1 d . . . O7 O 0.1520(9) -0.0592(4) 0.3791(5) 0.160(5) Uani 1 1 d . . . O8 O -0.0445(9) -0.0572(4) 0.3831(4) 0.139(4) Uani 1 1 d . . . O9 O -0.0102(7) 0.2380(3) 0.2701(3) 0.104(3) Uani 1 1 d . . . N1 N 0.4413(13) 0.0094(4) 0.6144(4) 0.103(3) Uani 1 1 d . . . N2 N 0.4666(7) 0.2730(3) 0.6652(3) 0.066(2) Uani 1 1 d . . . H2 H 0.4753 0.2807 0.6959 0.079 Uiso 1 1 calc R . . N3 N 0.2449(10) -0.0005(4) 0.4947(4) 0.101(3) Uani 1 1 d . . . N4 N 0.2785(7) 0.2711(3) 0.5077(2) 0.062(2) Uani 1 1 d . . . H4 H 0.3120 0.2870 0.5346 0.075 Uiso 1 1 calc R . . N5 N 0.0546(12) -0.0317(4) 0.3787(4) 0.097(3) Uani 1 1 d . . . N6 N 0.0523(4) 0.23985(18) 0.34913(13) 0.068(2) Uani 1 1 d . . . H6 H 0.0688 0.2638 0.3744 0.082 Uiso 1 1 calc R . . C1 C 0.4457(4) 0.07787(18) 0.62574(13) 0.073(3) Uani 1 1 d R . . C2 C 0.5622(4) 0.10933(18) 0.62896(13) 0.115(4) Uani 1 1 d R . . H2A H 0.6351 0.0863 0.6234 0.138 Uiso 1 1 calc R . . C3 C 0.5696(4) 0.17522(18) 0.64055(13) 0.109(4) Uani 1 1 d RD . . C4 C 0.4605(4) 0.20964(18) 0.64891(13) 0.064(2) Uani 1 1 d R . . C5 C 0.3440(4) 0.17818(18) 0.64569(13) 0.094(3) Uani 1 1 d R . . C6 C 0.3366(4) 0.11229(18) 0.63411(13) 0.105(4) Uani 1 1 d R . . H6A H 0.2587 0.0912 0.6320 0.126 Uiso 1 1 calc R . . C7 C 0.2089(19) 0.2203(7) 0.6435(8) 0.171(7) Uani 1 1 d . . . H7A H 0.2190 0.2641 0.6312 0.205 Uiso 1 1 calc R . . H7B H 0.1411 0.1984 0.6243 0.205 Uiso 1 1 calc R . . C8 C 0.191(2) 0.2202(10) 0.6881(8) 0.241(12) Uani 1 1 d . . . H8A H 0.2313 0.1826 0.7033 0.290 Uiso 1 1 calc R . . H8B H 0.1021 0.2188 0.6920 0.290 Uiso 1 1 calc R . . H8C H 0.2269 0.2590 0.7031 0.290 Uiso 1 1 calc R . . C9 C 0.6914(11) 0.2144(8) 0.6348(11) 0.281(18) Uani 1 1 d D . . H9A H 0.7322 0.1933 0.6087 0.337 Uiso 1 1 calc R . . H9B H 0.6639 0.2568 0.6225 0.337 Uiso 1 1 calc R . . C10 C 0.759(2) 0.2230(12) 0.6603(12) 0.33(2) Uani 1 1 d . . . H10A H 0.7230 0.2425 0.6877 0.390 Uiso 1 1 calc R . . H10B H 0.8196 0.2521 0.6482 0.390 Uiso 1 1 calc R . . H10C H 0.7994 0.1827 0.6701 0.390 Uiso 1 1 calc R . . C11 C 0.4592(4) 0.32256(19) 0.63405(16) 0.057(2) Uani 1 1 d . . . C12 C 0.4745(4) 0.38958(19) 0.65585(16) 0.066(3) Uani 1 1 d R . . C13 C 0.4869(4) 0.40195(19) 0.70548(16) 0.101(4) Uani 1 1 d R . . H13 H 0.4844 0.3677 0.7274 0.121 Uiso 1 1 calc R . . C14 C 0.5032(4) 0.46549(19) 0.72230(16) 0.114(4) Uani 1 1 d R . . H14 H 0.5115 0.4738 0.7555 0.137 Uiso 1 1 calc R . . C15 C 0.5070(4) 0.51667(19) 0.68948(16) 0.094(3) Uani 1 1 d R . . C16 C 0.4946(4) 0.50430(19) 0.63985(16) 0.099(4) Uani 1 1 d R . . H16 H 0.4972 0.5385 0.6179 0.119 Uiso 1 1 calc R . . C17 C 0.4784(4) 0.44076(19) 0.62303(16) 0.085(3) Uani 1 1 d R . . H17 H 0.4701 0.4325 0.5898 0.102 Uiso 1 1 calc R . . C18 C 0.5134(17) 0.5876(5) 0.7077(5) 0.129(5) Uani 1 1 d . . . C19 C 0.523(2) 0.5929(6) 0.7597(7) 0.216(9) Uani 1 1 d . . . H19A H 0.5991 0.5715 0.7728 0.259 Uiso 1 1 calc R . . H19B H 0.4511 0.5727 0.7723 0.259 Uiso 1 1 calc R . . H19C H 0.5264 0.6381 0.7688 0.259 Uiso 1 1 calc R . . C20 C 0.623(3) 0.6165(9) 0.6906(11) 0.39(3) Uani 1 1 d . . . H20A H 0.6972 0.5974 0.7071 0.471 Uiso 1 1 calc R . . H20B H 0.6224 0.6625 0.6969 0.471 Uiso 1 1 calc R . . H20C H 0.6235 0.6092 0.6563 0.471 Uiso 1 1 calc R . . C21 C 0.3992(13) 0.6278(5) 0.6892(7) 0.299(17) Uani 1 1 d . . . H21A H 0.4089 0.6717 0.7009 0.359 Uiso 1 1 calc R . . H21B H 0.3240 0.6091 0.7005 0.359 Uiso 1 1 calc R . . H21C H 0.3925 0.6280 0.6543 0.359 Uiso 1 1 calc R . . C22 C 0.2550(4) 0.06989(18) 0.49645(13) 0.064(3) Uani 1 1 d R . . C23 C 0.3725(4) 0.10014(18) 0.49705(13) 0.074(3) Uani 1 1 d R . . H23 H 0.4453 0.0752 0.4956 0.089 Uiso 1 1 calc R . . C24 C 0.3810(4) 0.1677(2) 0.49987(13) 0.070(3) Uani 1 1 d R . . C25 C 0.2722(4) 0.20492(18) 0.50208(13) 0.059(2) Uani 1 1 d R . . C26 C 0.1547(4) 0.17468(18) 0.50148(13) 0.066(3) Uani 1 1 d R . . C27 C 0.1462(4) 0.10716(19) 0.49866(14) 0.074(3) Uani 1 1 d R . . H27 H 0.0676 0.0869 0.4983 0.088 Uiso 1 1 calc R . . C28 C 0.0357(10) 0.2127(5) 0.5077(5) 0.112(4) Uani 1 1 d . . . H28A H 0.0570 0.2451 0.5326 0.134 Uiso 1 1 calc R . . H28B H 0.0159 0.2364 0.4777 0.134 Uiso 1 1 calc R . . C29 C -0.0725(12) 0.1840(6) 0.5191(7) 0.164(7) Uani 1 1 d . . . H29A H -0.0962 0.1509 0.4955 0.196 Uiso 1 1 calc R . . H29B H -0.1385 0.2161 0.5190 0.196 Uiso 1 1 calc R . . H29C H -0.0599 0.1647 0.5507 0.196 Uiso 1 1 calc R . . C30 C 0.5068(10) 0.1980(5) 0.5013(5) 0.095(3) Uani 1 1 d . . . H30A H 0.5027 0.2404 0.5167 0.114 Uiso 1 1 calc R . . H30B H 0.5658 0.1715 0.5215 0.114 Uiso 1 1 calc R . . C31 C 0.5528(16) 0.2058(8) 0.4573(6) 0.198(9) Uani 1 1 d . . . H31A H 0.5554 0.1644 0.4413 0.237 Uiso 1 1 calc R . . H31B H 0.6367 0.2237 0.4615 0.237 Uiso 1 1 calc R . . H31C H 0.4990 0.2350 0.4379 0.237 Uiso 1 1 calc R . . C32 C 0.2351(3) 0.31033(15) 0.47363(14) 0.063(3) Uani 1 1 d . . . C33 C 0.2401(3) 0.38214(15) 0.48160(14) 0.054(2) Uani 1 1 d R . . C34 C 0.2306(3) 0.40832(15) 0.52757(14) 0.080(3) Uani 1 1 d R . . H34 H 0.2234 0.3809 0.5540 0.096 Uiso 1 1 calc R . . C35 C 0.2320(3) 0.47551(15) 0.53404(14) 0.088(3) Uani 1 1 d R . . H35 H 0.2256 0.4930 0.5648 0.106 Uiso 1 1 calc R . . C36 C 0.2428(3) 0.51651(15) 0.49453(14) 0.070(3) Uani 1 1 d R . . C37 C 0.2523(3) 0.49033(15) 0.44856(14) 0.095(4) Uani 1 1 d R . . H37 H 0.2596 0.5178 0.4221 0.114 Uiso 1 1 calc R . . C38 C 0.2510(3) 0.42314(15) 0.44209(14) 0.096(4) Uani 1 1 d R . . H38 H 0.2573 0.4056 0.4113 0.115 Uiso 1 1 calc R . . C39 C 0.2389(12) 0.5909(4) 0.5011(4) 0.094(3) Uani 1 1 d . . . C40 C 0.375(2) 0.6077(6) 0.5156(10) 0.295(15) Uani 1 1 d . . . H40A H 0.3948 0.5975 0.5493 0.354 Uiso 1 1 calc R . . H40B H 0.3887 0.6534 0.5106 0.354 Uiso 1 1 calc R . . H40C H 0.4295 0.5830 0.4963 0.354 Uiso 1 1 calc R . . C41 C 0.168(2) 0.6113(5) 0.5412(6) 0.232(12) Uani 1 1 d . . . H41A H 0.0851 0.5918 0.5379 0.279 Uiso 1 1 calc R . . H41B H 0.1592 0.6579 0.5408 0.279 Uiso 1 1 calc R . . H41C H 0.2113 0.5978 0.5713 0.279 Uiso 1 1 calc R . . C42 C 0.216(2) 0.6291(2) 0.45091(18) 0.287(14) Uani 1 1 d . . . H42A H 0.1391 0.6141 0.4338 0.345 Uiso 1 1 calc R . . H42B H 0.2858 0.6213 0.4315 0.345 Uiso 1 1 calc R . . H42C H 0.2098 0.6750 0.4572 0.345 Uiso 1 1 calc R . . C43 C 0.0584(5) 0.0378(2) 0.37125(15) 0.076(3) Uani 1 1 d R . . C44 C 0.1724(5) 0.0688(2) 0.36463(15) 0.089(3) Uani 1 1 d R . . H44 H 0.2469 0.0447 0.3655 0.107 Uiso 1 1 calc R . . C45 C 0.1751(5) 0.1356(2) 0.35674(15) 0.076(3) Uani 1 1 d R . . C46 C 0.0637(4) 0.1716(2) 0.35548(15) 0.068(3) Uani 1 1 d R . . C47 C -0.0503(4) 0.1407(2) 0.36210(15) 0.098(4) Uani 1 1 d R . . C48 C -0.0529(4) 0.0738(2) 0.36998(15) 0.105(4) Uani 1 1 d R . . H48 H -0.1292 0.0531 0.3744 0.126 Uiso 1 1 calc R . . C49 C 0.2890(12) 0.1724(6) 0.3519(6) 0.123(5) Uani 1 1 d . . . H49A H 0.2797 0.2156 0.3654 0.148 Uiso 1 1 calc R . . H49B H 0.3593 0.1511 0.3702 0.148 Uiso 1 1 calc R . . C50 C 0.3142(18) 0.1775(8) 0.3051(8) 0.213(10) Uani 1 1 d . . . H50A H 0.3069 0.1353 0.2900 0.256 Uiso 1 1 calc R . . H50B H 0.3986 0.1937 0.3034 0.256 Uiso 1 1 calc R . . H50C H 0.2550 0.2069 0.2886 0.256 Uiso 1 1 calc R . . C51 C -0.1804(13) 0.1791(7) 0.3747(8) 0.157(6) Uani 1 1 d . . . H51A H -0.2158 0.1595 0.4026 0.188 Uiso 1 1 calc R . . H51B H -0.1628 0.2247 0.3818 0.188 Uiso 1 1 calc R . . C52 C -0.259(2) 0.1732(9) 0.3358(7) 0.208(9) Uani 1 1 d . . . H52A H -0.2146 0.1822 0.3075 0.249 Uiso 1 1 calc R . . H52B H -0.3272 0.2034 0.3375 0.249 Uiso 1 1 calc R . . H52C H -0.2912 0.1295 0.3339 0.249 Uiso 1 1 calc R . . C53 C 0.0190(4) 0.2697(2) 0.30842(17) 0.073(3) Uani 1 1 d . . . C54 C 0.0081(4) 0.3403(2) 0.30794(17) 0.073(3) Uani 1 1 d R . . C55 C 0.0134(4) 0.3753(2) 0.35113(17) 0.102(4) Uani 1 1 d R . . H55 H 0.0260 0.3537 0.3807 0.122 Uiso 1 1 calc R . . C56 C -0.0001(4) 0.4427(2) 0.35010(17) 0.125(5) Uani 1 1 d R . . H56 H 0.0035 0.4661 0.3790 0.150 Uiso 1 1 calc R . . C57 C -0.0189(4) 0.4750(2) 0.30590(17) 0.090(3) Uani 1 1 d R . . C58 C -0.0242(4) 0.4400(2) 0.26271(17) 0.148(6) Uani 1 1 d R . . H58 H -0.0368 0.4616 0.2331 0.178 Uiso 1 1 calc R . . C59 C -0.0107(4) 0.3726(2) 0.26373(17) 0.158(7) Uani 1 1 d R . . H59 H -0.0143 0.3492 0.2348 0.189 Uiso 1 1 calc R . . C60 C -0.0257(16) 0.5514(5) 0.3057(5) 0.118(4) Uani 1 1 d . . . C61 C 0.1093(19) 0.5785(7) 0.3108(7) 0.199(8) Uani 1 1 d . . . H61A H 0.1559 0.5614 0.2852 0.238 Uiso 1 1 calc R . . H61B H 0.1500 0.5658 0.3417 0.238 Uiso 1 1 calc R . . H61C H 0.1066 0.6252 0.3087 0.238 Uiso 1 1 calc R . . C62 C -0.093(2) 0.5755(6) 0.3475(7) 0.230(11) Uani 1 1 d . . . H62A H -0.1009 0.6220 0.3457 0.276 Uiso 1 1 calc R . . H62B H -0.0462 0.5636 0.3774 0.276 Uiso 1 1 calc R . . H62C H -0.1760 0.5562 0.3464 0.276 Uiso 1 1 calc R . . C63 C -0.083(2) 0.5740(6) 0.2587(6) 0.228(11) Uani 1 1 d . . . H63A H -0.1637 0.5537 0.2519 0.273 Uiso 1 1 calc R . . H63B H -0.0285 0.5628 0.2337 0.273 Uiso 1 1 calc R . . H63C H -0.0932 0.6205 0.2595 0.273 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 O1 0.122(9) 0.080(6) 0.366(18) -0.036(8) 0.017(10) 0.024(6) O2 0.118(8) 0.083(6) 0.340(17) -0.048(8) 0.035(9) -0.029(6) O3 0.105(5) 0.077(4) 0.049(4) -0.008(3) -0.018(4) 0.002(3) O4 0.094(6) 0.061(5) 0.268(12) -0.028(6) 0.005(7) 0.020(4) O5 0.084(6) 0.054(4) 0.337(15) -0.024(6) 0.045(8) -0.023(4) O6 0.145(6) 0.051(3) 0.070(5) -0.006(3) -0.027(4) 0.005(4) O7 0.102(7) 0.079(5) 0.304(14) 0.043(7) 0.043(8) 0.032(5) O8 0.112(8) 0.087(6) 0.217(10) 0.035(6) 0.010(7) -0.026(5) O9 0.153(7) 0.077(4) 0.077(5) -0.006(4) -0.013(5) -0.006(4) N1 0.111(10) 0.056(6) 0.142(9) -0.014(5) 0.017(7) -0.009(6) N2 0.084(6) 0.059(5) 0.056(5) -0.006(4) 0.018(4) -0.002(4) N3 0.078(8) 0.052(6) 0.171(10) 0.000(6) 0.002(7) 0.007(6) N4 0.104(6) 0.031(4) 0.049(4) 0.002(3) -0.010(4) -0.004(4) N5 0.090(9) 0.078(7) 0.124(8) 0.011(6) 0.011(7) -0.012(6) N6 0.095(6) 0.053(4) 0.056(5) 0.000(4) 0.003(4) 0.004(4) C1 0.074(8) 0.073(7) 0.072(7) 0.005(5) 0.007(6) -0.002(5) C2 0.072(8) 0.070(7) 0.205(14) -0.012(7) 0.031(8) 0.005(6) C3 0.059(7) 0.076(7) 0.194(13) -0.019(7) 0.019(8) 0.008(6) C4 0.069(7) 0.058(6) 0.063(6) -0.001(5) 0.003(5) -0.004(5) C5 0.081(8) 0.062(6) 0.142(10) -0.013(6) 0.025(7) 0.004(6) C6 0.062(8) 0.104(9) 0.154(11) -0.018(8) 0.035(8) -0.002(6) C7 0.196(18) 0.106(11) 0.22(2) -0.030(13) 0.090(17) -0.050(11) C8 0.29(3) 0.185(19) 0.27(3) 0.05(2) 0.13(3) -0.063(18) C9 0.048(13) 0.147(14) 0.64(5) -0.15(2) -0.01(2) 0.004(11) C10 0.083(17) 0.21(2) 0.67(6) -0.13(3) -0.05(2) 0.002(16) C11 0.059(6) 0.052(5) 0.057(6) 0.003(5) -0.011(5) -0.001(4) C12 0.059(6) 0.078(6) 0.061(6) -0.013(5) 0.002(5) 0.005(5) C13 0.144(11) 0.088(8) 0.070(8) -0.017(6) 0.008(7) -0.001(7) C14 0.174(13) 0.084(8) 0.083(8) -0.015(7) -0.001(8) -0.002(8) C15 0.105(9) 0.080(7) 0.101(9) -0.030(7) 0.027(7) -0.019(6) C16 0.141(11) 0.063(6) 0.097(9) -0.007(6) 0.035(8) -0.011(6) C17 0.111(9) 0.073(6) 0.072(7) 0.003(5) 0.010(6) -0.002(6) C18 0.197(15) 0.071(7) 0.122(11) -0.036(7) 0.027(10) -0.035(9) C19 0.34(3) 0.111(11) 0.197(19) -0.077(12) 0.016(18) -0.004(13) C20 0.49(4) 0.163(16) 0.59(5) -0.25(2) 0.39(4) -0.22(3) C21 0.37(3) 0.123(13) 0.38(3) -0.111(17) -0.15(3) 0.115(19) C22 0.061(7) 0.034(5) 0.099(7) -0.002(4) 0.007(5) 0.001(5) C23 0.074(7) 0.034(5) 0.113(8) -0.010(5) 0.002(6) 0.004(5) C24 0.061(7) 0.066(6) 0.083(7) -0.009(5) 0.009(5) -0.004(5) C25 0.065(7) 0.050(5) 0.060(6) -0.007(4) -0.004(5) -0.012(5) C26 0.064(7) 0.052(5) 0.081(7) -0.003(5) -0.004(5) 0.014(5) C27 0.063(7) 0.058(6) 0.100(8) -0.010(5) 0.004(6) 0.000(5) C28 0.067(8) 0.076(7) 0.189(13) -0.027(7) -0.014(8) -0.004(6) C29 0.087(10) 0.087(8) 0.32(2) -0.020(11) 0.057(12) 0.008(8) C30 0.078(8) 0.081(7) 0.129(10) -0.019(7) 0.037(7) -0.021(6) C31 0.188(17) 0.212(17) 0.212(18) -0.105(14) 0.137(15) -0.114(14) C32 0.093(7) 0.045(5) 0.051(6) -0.010(5) 0.002(5) -0.010(5) C33 0.066(6) 0.046(5) 0.051(6) -0.003(4) 0.008(5) 0.001(4) C34 0.118(9) 0.055(6) 0.070(7) 0.000(5) 0.016(6) -0.009(5) C35 0.147(11) 0.051(5) 0.070(7) -0.009(5) 0.030(7) 0.009(6) C36 0.075(7) 0.053(5) 0.084(7) 0.011(5) 0.024(5) -0.003(4) C37 0.171(12) 0.052(6) 0.069(7) 0.005(5) 0.044(7) -0.001(6) C38 0.163(11) 0.053(6) 0.074(7) -0.001(5) 0.018(7) 0.003(6) C39 0.123(10) 0.050(6) 0.110(9) -0.014(6) 0.020(8) -0.013(6) C40 0.29(3) 0.057(9) 0.53(5) -0.062(16) -0.02(3) -0.061(13) C41 0.42(3) 0.058(7) 0.250(19) -0.024(10) 0.24(2) 0.014(12) C42 0.61(5) 0.056(8) 0.192(18) 0.034(10) 0.02(2) 0.076(16) C43 0.077(8) 0.075(7) 0.076(7) 0.018(5) 0.016(6) -0.017(6) C44 0.092(9) 0.062(6) 0.116(9) 0.010(6) 0.020(7) 0.013(6) C45 0.052(7) 0.097(7) 0.082(7) 0.004(6) 0.018(5) 0.008(6) C46 0.067(7) 0.061(6) 0.077(7) 0.002(5) 0.013(5) -0.011(5) C47 0.066(8) 0.069(7) 0.158(11) 0.011(7) 0.008(7) 0.015(6) C48 0.054(7) 0.080(7) 0.180(13) 0.011(7) 0.009(7) 0.005(6) C49 0.091(10) 0.104(9) 0.182(15) -0.018(10) 0.064(10) 0.007(7) C50 0.186(18) 0.172(16) 0.30(3) -0.070(17) 0.151(19) -0.023(13) C51 0.101(12) 0.130(12) 0.24(2) 0.024(12) 0.001(12) -0.013(9) C52 0.19(2) 0.204(19) 0.22(2) 0.051(15) -0.033(17) 0.036(15) C53 0.091(8) 0.068(6) 0.063(7) 0.002(5) 0.012(6) -0.002(5) C54 0.076(7) 0.070(6) 0.071(7) 0.004(5) -0.012(6) 0.003(5) C55 0.168(12) 0.072(7) 0.064(7) 0.003(6) 0.005(7) 0.010(7) C56 0.232(16) 0.069(7) 0.075(8) 0.007(6) 0.023(9) 0.035(8) C57 0.102(9) 0.072(6) 0.092(8) 0.008(6) -0.003(7) 0.003(6) C58 0.28(2) 0.100(9) 0.062(8) 0.009(7) 0.010(10) -0.015(11) C59 0.31(2) 0.073(8) 0.082(9) 0.004(7) -0.030(11) 0.018(10) C60 0.185(15) 0.076(8) 0.096(10) 0.019(7) 0.019(10) 0.017(9) C61 0.25(2) 0.106(11) 0.24(2) 0.023(12) 0.014(18) -0.038(13) C62 0.39(3) 0.072(8) 0.25(2) 0.035(11) 0.19(2) 0.064(13) C63 0.42(3) 0.086(9) 0.165(16) 0.037(10) -0.066(18) 0.038(14) _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 O1 N1 1.161(12) . ? O2 N1 1.172(12) . ? O3 C11 1.193(7) . ? O4 N3 1.187(10) . ? O5 N3 1.189(10) . ? O6 C32 1.250(7) . ? O7 N5 1.175(11) . ? O8 N5 1.187(11) . ? O9 C53 1.261(7) . ? N1 C1 1.440(9) . ? N2 C11 1.330(8) . ? N2 C4 1.377(7) . ? N3 C22 1.448(9) . ? N4 C32 1.295(7) . ? N4 C25 1.368(6) . ? N5 C43 1.443(10) . ? N6 C53 1.304(5) . ? N6 C46 1.416(5) . ? C1 C2 1.3900 . ? C1 C6 1.3900 . ? C2 C3 1.3900 . ? C3 C4 1.3900 . ? C3 C9 1.5402(11) . ? C4 C5 1.3900 . ? C5 C6 1.3900 . ? C5 C7 1.671(19) . ? C7 C8 1.26(2) . ? C9 C10 0.98(3) . ? C11 C12 1.5048 . ? C12 C13 1.3900 . ? C12 C17 1.3900 . ? C13 C14 1.3900 . ? C14 C15 1.3900 . ? C15 C16 1.3900 . ? C15 C18 1.541(11) . ? C16 C17 1.3900 . ? C18 C20 1.42(2) . ? C18 C19 1.435(19) . ? C18 C21 1.520(17) . ? C22 C23 1.3900(13) . ? C22 C27 1.3900 . ? C23 C24 1.3900(11) . ? C24 C25 1.3900 . ? C24 C30 1.469(11) . ? C25 C26 1.3900(14) . ? C26 C27 1.3900 . ? C26 C28 1.505(11) . ? C28 C29 1.349(15) . ? C30 C31 1.356(16) . ? C32 C33 1.4901 . ? C33 C34 1.3900 . ? C33 C38 1.3900 . ? C34 C35 1.3900 . ? C35 C36 1.3900 . ? C36 C37 1.3900 . ? C36 C39 1.538(9) . ? C37 C38 1.3900 . ? C39 C41 1.452(16) . ? C39 C40 1.51(2) . ? C39 C42 1.594(11) . ? C43 C44 1.3900 . ? C43 C48 1.3900 . ? C44 C45 1.3900 . ? C45 C46 1.3900 . ? C45 C49 1.439(13) . ? C46 C47 1.3900(13) . ? C47 C48 1.3900 . ? C47 C51 1.650(16) . ? C49 C50 1.35(2) . ? C51 C52 1.310(19) . ? C53 C54 1.4524 . ? C54 C55 1.3900 . ? C54 C59 1.3900 . ? C55 C56 1.3900 . ? C56 C57 1.3900 . ? C57 C58 1.3900 . ? C57 C60 1.569(11) . ? C58 C59 1.3900 . ? C60 C63 1.465(17) . ? C60 C62 1.490(17) . ? C60 C61 1.53(2) . ? 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 O1 N1 O2 122.3(11) . . ? O1 N1 C1 119.5(11) . . ? O2 N1 C1 117.9(11) . . ? C11 N2 C4 120.7(6) . . ? O4 N3 O5 123.8(9) . . ? O4 N3 C22 117.7(9) . . ? O5 N3 C22 118.3(9) . . ? C32 N4 C25 121.5(5) . . ? O7 N5 O8 124.8(10) . . ? O7 N5 C43 116.1(10) . . ? O8 N5 C43 119.0(10) . . ? C53 N6 C46 125.9(4) . . ? C2 C1 C6 120.0 . . ? C2 C1 N1 118.7(6) . . ? C6 C1 N1 121.3(6) . . ? C3 C2 C1 120.0 . . ? C2 C3 C4 120.0 . . ? C2 C3 C9 121.1(7) . . ? C4 C3 C9 117.9(7) . . ? N2 C4 C5 118.5(3) . . ? N2 C4 C3 121.1(3) . . ? C5 C4 C3 120.0 . . ? C4 C5 C6 120.0 . . ? C4 C5 C7 121.1(5) . . ? C6 C5 C7 117.6(6) . . ? C5 C6 C1 120.0 . . ? C8 C7 C5 99(2) . . ? C10 C9 C3 126(3) . . ? O3 C11 N2 123.3(5) . . ? O3 C11 C12 120.5(3) . . ? N2 C11 C12 116.1(3) . . ? C13 C12 C17 120.0 . . ? C13 C12 C11 124.1 . . ? C17 C12 C11 115.9 . . ? C14 C13 C12 120.0 . . ? C13 C14 C15 120.0 . . ? C16 C15 C14 120.0 . . ? C16 C15 C18 119.6(6) . . ? C14 C15 C18 120.2(6) . . ? C15 C16 C17 120.0 . . ? C12 C17 C16 120.0 . . ? C20 C18 C19 107.8(18) . . ? C20 C18 C21 108.2(17) . . ? C19 C18 C21 106.8(15) . . ? C20 C18 C15 107.5(12) . . ? C19 C18 C15 113.4(11) . . ? C21 C18 C15 112.9(10) . . ? C23 C22 C27 120.0 . . ? C23 C22 N3 120.6(5) . . ? C27 C22 N3 119.4(5) . . ? C24 C23 C22 120.00(6) . . ? C23 C24 C25 120.0 . . ? C23 C24 C30 118.6(4) . . ? C25 C24 C30 121.4(5) . . ? N4 C25 C26 118.7(4) . . ? N4 C25 C24 121.2(3) . . ? C26 C25 C24 120.0 . . ? C25 C26 C27 120.00(7) . . ? C25 C26 C28 121.7(4) . . ? C27 C26 C28 118.1(4) . . ? C26 C27 C22 120.0 . . ? C29 C28 C26 122.5(9) . . ? C31 C30 C24 114.6(11) . . ? O6 C32 N4 122.8(4) . . ? O6 C32 C33 117.1(3) . . ? N4 C32 C33 120.0(3) . . ? C34 C33 C38 120.0 . . ? C34 C33 C32 120.8 . . ? C38 C33 C32 119.1 . . ? C33 C34 C35 120.0 . . ? C34 C35 C36 120.0 . . ? C37 C36 C35 120.0 . . ? C37 C36 C39 119.7(5) . . ? C35 C36 C39 120.2(5) . . ? C38 C37 C36 120.0 . . ? C37 C38 C33 120.0 . . ? C41 C39 C40 106.1(15) . . ? C41 C39 C36 113.4(9) . . ? C40 C39 C36 102.9(9) . . ? C41 C39 C42 118.0(12) . . ? C40 C39 C42 101.1(14) . . ? C36 C39 C42 113.0(7) . . ? C44 C43 C48 120.0 . . ? C44 C43 N5 120.3(6) . . ? C48 C43 N5 119.7(6) . . ? C43 C44 C45 120.00(6) . . ? C46 C45 C44 120.00(8) . . ? C46 C45 C49 115.9(5) . . ? C44 C45 C49 124.0(5) . . ? C45 C46 C47 120.0 . . ? C45 C46 N6 126.3(3) . . ? C47 C46 N6 113.7(3) . . ? C48 C47 C46 120.00(6) . . ? C48 C47 C51 114.3(5) . . ? C46 C47 C51 124.0(5) . . ? C47 C48 C43 120.00(7) . . ? C50 C49 C45 111.2(14) . . ? C52 C51 C47 105.4(17) . . ? O9 C53 N6 120.9(4) . . ? O9 C53 C54 119.6(3) . . ? N6 C53 C54 119.5(2) . . ? C55 C54 C59 120.0 . . ? C55 C54 C53 120.7 . . ? C59 C54 C53 119.3 . . ? C56 C55 C54 120.0 . . ? C57 C56 C55 120.0 . . ? C56 C57 C58 120.0 . . ? C56 C57 C60 118.9(5) . . ? C58 C57 C60 121.0(5) . . ? C57 C58 C59 120.0 . . ? C58 C59 C54 120.0 . . ? C63 C60 C62 113.2(15) . . ? C63 C60 C61 106.4(14) . . ? C62 C60 C61 108.3(15) . . ? C63 C60 C57 109.5(10) . . ? C62 C60 C57 110.7(10) . . ? C61 C60 C57 108.6(11) . . ? _diffrn_measured_fraction_theta_max 0.841 _diffrn_reflns_theta_full 20.99 _diffrn_measured_fraction_theta_full 0.841 _refine_diff_density_max 0.375 _refine_diff_density_min -0.333 _refine_diff_density_rms 0.063 data_gah15 _database_code_CSD 158585 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common '4 nitro N-2,6 diisopropylphenyl 4 t-butylbenzamide' _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C23 H30 N2 O3' _chemical_formula_weight 382.49 _chemical_melting_point ? _chemical_compound_source ? 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' 'O' 'O' 0.0106 0.0060 '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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M I2/a loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y, -z' 'x+1/2, y+1/2, z+1/2' '-x+1, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y, z' '-x+1/2, -y+1/2, -z+1/2' 'x, -y+1/2, z+1/2' _cell_length_a 19.540(42) _cell_length_b 10.668(32) _cell_length_c 24.230(72) _cell_angle_alpha 90.00 _cell_angle_beta 113.77(19) _cell_angle_gamma 90.00 _cell_volume 4622.4(218) _cell_formula_units_Z 8 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.099 _exptl_crystal_density_method ? _exptl_crystal_F_000 1648 _exptl_absorpt_coefficient_mu 0.073 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Rigaku R-axis IIc' _diffrn_measurement_method 'Image plate scans' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5289 _diffrn_reflns_av_R_equivalents 0.1019 _diffrn_reflns_av_sigmaI/netI 0.0747 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.84 _diffrn_reflns_theta_max 18.85 _reflns_number_total 1669 _reflns_number_observed 1422 _reflns_observed_criterion >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 2 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.3020P)^2^+125.1398P] 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 ? _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0034(28) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 1667 _refine_ls_number_parameters 318 _refine_ls_number_restraints 451 _refine_ls_R_factor_all 0.2374 _refine_ls_R_factor_obs 0.2215 _refine_ls_wR_factor_all 0.5635 _refine_ls_wR_factor_obs 0.5464 _refine_ls_goodness_of_fit_all 1.115 _refine_ls_goodness_of_fit_obs 1.191 _refine_ls_restrained_S_all 1.336 _refine_ls_restrained_S_obs 1.398 _refine_ls_shift/esd_max -0.076 _refine_ls_shift/esd_mean 0.014 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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group O1 O 1.0201(25) 0.1593(33) 0.7720(12) 0.259(25) Uani 1 d . 1 O2 O 1.0047(14) -0.0211(32) 0.7784(11) 0.147(10) Uani 1 d . 1 O3 O 0.7607(14) 0.0708(30) 0.4766(12) 0.088(9) Uani 0.50 d PDU 1 N1 N 1.0026(23) 0.0669(51) 0.7473(15) 0.167(16) Uani 1 d . 1 N2 N 0.8747(4) 0.0351(8) 0.5036(4) 0.066(5) Uani 1.00 d PD 1 H2 H 0.9083(4) 0.0214(8) 0.4898(4) 0.079 Uiso 0.50 calc PR 1 C1 C 0.9667(4) 0.0579(8) 0.6849(4) 0.112(11) Uani 1 d R 1 C2 C 0.9591(4) 0.1655(8) 0.6506(4) 0.085(8) Uani 1 d R 1 H2A H 0.9744(4) 0.2426(8) 0.6695(4) 0.102 Uiso 1 calc R 1 C3 C 0.9287(4) 0.1578(8) 0.5880(4) 0.065(7) Uani 1 d RD 1 C4 C 0.9058(4) 0.0426(8) 0.5598(4) 0.029(5) Uani 1 d RDU 1 C5 C 0.9134(4) -0.0650(8) 0.5941(4) 0.063(6) Uani 1 d RD 1 C6 C 0.9439(4) -0.0573(8) 0.6567(4) 0.078(8) Uani 1 d R 1 H6 H 0.9490(4) -0.1293(8) 0.6797(4) 0.093 Uiso 1 calc R 1 C7 C 0.9192(15) 0.2780(20) 0.5505(10) 0.108(11) Uani 1 d D 1 H7 H 0.9043(15) 0.2523(20) 0.5085(10) 0.129 Uiso 1 calc R 1 C8 C 0.9940(15) 0.3434(26) 0.5698(15) 0.128(11) Uani 1 d D 1 H8A H 0.9954(39) 0.3904(134) 0.5365(28) 0.153 Uiso 1 calc R 1 H8B H 1.0333(16) 0.2821(28) 0.5824(76) 0.153 Uiso 1 calc R 1 H8C H 1.0008(46) 0.3991(128) 0.6027(55) 0.153 Uiso 1 calc R 1 C9 C 0.8595(15) 0.3635(28) 0.5525(17) 0.154(15) Uani 1 d D 1 H9A H 0.8223(65) 0.3151(37) 0.5595(100) 0.184 Uiso 1 calc R 1 H9B H 0.8366(82) 0.4069(152) 0.5148(37) 0.184 Uiso 1 calc R 1 H9C H 0.8812(25) 0.4232(132) 0.5845(62) 0.184 Uiso 1 calc R 1 C10 C 0.8880(15) -0.1905(19) 0.5627(9) 0.084(8) Uani 1 d D 1 H10 H 0.8607(15) -0.1755(19) 0.5193(9) 0.101 Uiso 1 calc R 1 C11 C 0.8362(16) -0.2562(27) 0.5862(14) 0.145(14) Uani 1 d D 1 H11A H 0.8076(78) -0.1948(28) 0.5968(81) 0.174 Uiso 1 calc R 1 H11B H 0.8654(18) -0.3047(145) 0.6212(53) 0.174 Uiso 1 calc R 1 H11C H 0.8030(73) -0.3106(137) 0.5556(34) 0.174 Uiso 1 calc R 1 C12 C 0.9551(20) -0.2740(31) 0.5720(17) 0.176(17) Uani 1 d D 1 H12A H 0.9974(40) -0.2227(31) 0.5766(110) 0.211 Uiso 1 calc R 1 H12B H 0.9435(51) -0.3280(160) 0.5378(52) 0.211 Uiso 1 calc R 1 H12C H 0.9666(87) -0.3238(168) 0.6076(64) 0.211 Uiso 1 calc R 1 C13 C 0.8094(7) 0.0406(15) 0.4583(6) 0.057(10) Uani 0.50 d PDU 1 C14 C 0.7951(7) 0.0481(15) 0.3862(6) 0.057(10) Uani 0.50 d PRDU 1 C15 C 0.7208(7) 0.0759(15) 0.3505(6) 0.080(11) Uani 0.50 d PRDU 1 H15 H 0.6879(7) 0.0945(15) 0.3684(6) 0.096 Uiso 0.50 calc PR 1 C16 C 0.6956(7) 0.0760(15) 0.2881(6) 0.070(11) Uani 0.50 d PRDU 1 H16 H 0.6459(7) 0.0946(15) 0.2642(6) 0.084 Uiso 0.50 calc PR 1 C17 C 0.7447(7) 0.0482(15) 0.2613(6) 0.041(9) Uani 0.50 d PRDU 1 C18 C 0.8190(7) 0.0204(15) 0.2970(6) 0.066(10) Uani 0.50 d PRDU 1 H18 H 0.8519(7) 0.0018(15) 0.2791(6) 0.079 Uiso 0.50 calc PR 1 C19 C 0.8442(7) 0.0203(15) 0.3595(6) 0.099(14) Uani 0.50 d PRDU 1 H19 H 0.8939(7) 0.0017(15) 0.3834(6) 0.119 Uiso 0.50 calc PR 1 C20 C 0.7197(21) 0.0433(34) 0.1941(11) 0.055(11) Uani 0.50 d PDU 1 C21 C 0.6469(23) 0.0681(57) 0.1584(20) 0.125(27) Uani 0.50 d PDU 1 H21A H 0.6162(31) 0.0465(320) 0.1795(66) 0.150 Uiso 0.50 calc PR 1 H21B H 0.6318(64) 0.0196(263) 0.1221(76) 0.150 Uiso 0.50 calc PR 1 H21C H 0.6413(42) 0.1557(87) 0.1485(135) 0.150 Uiso 0.50 calc PR 1 C22 C 0.7779(29) 0.1047(51) 0.1753(19) 0.098(17) Uani 0.50 d PDU 1 H22A H 0.8179(89) 0.0468(114) 0.1815(132) 0.118 Uiso 0.50 calc PR 1 H22B H 0.7974(132) 0.1785(169) 0.1992(100) 0.118 Uiso 0.50 calc PR 1 H22C H 0.7548(49) 0.1275(271) 0.1335(42) 0.118 Uiso 0.50 calc PR 1 C23 C 0.7342(35) -0.1101(40) 0.1813(21) 0.131(24) Uani 0.50 d PDU 1 H23A H 0.7092(196) -0.1634(40) 0.1992(164) 0.157 Uiso 0.50 calc PR 1 H23B H 0.7868(36) -0.1277(110) 0.1988(168) 0.157 Uiso 0.50 calc PR 1 H23C H 0.7146(219) -0.1253(106) 0.1387(21) 0.157 Uiso 0.50 calc PR 1 O4 O 0.9684(15) 0.0126(34) 0.4774(12) 0.102(12) Uani 0.50 d PDU 2 H2A1 H 0.8269(10) 0.0261(16) 0.4890(7) 0.079 Uiso 0.50 calc PR 2 C24 C 0.9036(10) 0.0388(16) 0.4642(7) 0.060(12) Uani 0.50 d PD 2 C25 C 0.8563(10) 0.0021(16) 0.3866(7) 0.061(10) Uani 0.50 d PRDU 2 C26 C 0.7800(10) 0.0263(16) 0.3617(7) 0.098(13) Uani 0.50 d PRDU 2 H26 H 0.7560(10) 0.0490(16) 0.3864(7) 0.118 Uiso 0.50 calc PR 2 C27 C 0.7395(10) 0.0164(16) 0.2997(7) 0.083(12) Uani 0.50 d PRDU 2 H27 H 0.6883(10) 0.0325(16) 0.2830(7) 0.100 Uiso 0.50 calc PR 2 C28 C 0.7753(10) -0.0176(16) 0.2627(7) 0.058(10) Uani 0.50 d PRDU 2 C29 C 0.8517(10) -0.0417(16) 0.2877(7) 0.109(15) Uani 0.50 d PRDU 2 H29 H 0.8757(10) -0.0645(16) 0.2630(7) 0.131 Uiso 0.50 calc PR 2 C30 C 0.8922(10) -0.0319(16) 0.3496(7) 0.106(13) Uani 0.50 d PRDU 2 H30 H 0.9433(10) -0.0480(16) 0.3663(7) 0.127 Uiso 0.50 calc PR 2 C31 C 0.7304(22) -0.0215(39) 0.1955(12) 0.078(14) Uani 0.50 d PDU 2 C32 C 0.6712(25) 0.1019(43) 0.1782(18) 0.076(16) Uani 0.50 d PDU 2 H32A H 0.6485(119) 0.1127(166) 0.1352(20) 0.092 Uiso 0.50 calc PR 2 H32B H 0.6984(33) 0.1764(57) 0.1967(102) 0.092 Uiso 0.50 calc PR 2 H32C H 0.6330(85) 0.0868(111) 0.1928(106) 0.092 Uiso 0.50 calc PR 2 C33 C 0.7784(26) 0.0136(52) 0.1635(18) 0.106(19) Uani 0.50 d PDU 2 H33A H 0.8209(99) -0.0414(210) 0.1758(115) 0.128 Uiso 0.50 calc PR 2 H33B H 0.7952(162) 0.0985(118) 0.1733(125) 0.128 Uiso 0.50 calc PR 2 H33C H 0.7503(58) 0.0062(313) 0.1208(18) 0.128 Uiso 0.50 calc PR 2 C34 C 0.6843(28) -0.1267(41) 0.1753(20) 0.109(20) Uani 0.50 d PDU 2 H34A H 0.6343(45) -0.1004(43) 0.1505(120) 0.131 Uiso 0.50 calc PR 2 H34B H 0.6843(148) -0.1729(169) 0.2093(21) 0.131 Uiso 0.50 calc PR 2 H34C H 0.7028(105) -0.1792(156) 0.1521(125) 0.131 Uiso 0.50 calc PR 2 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 O1 0.494(67) 0.154(27) 0.072(18) -0.053(18) 0.053(24) -0.054(30) O2 0.143(20) 0.221(31) 0.048(15) -0.030(16) 0.007(14) 0.012(19) O3 0.098(18) 0.110(18) 0.057(16) 0.008(13) 0.033(14) 0.004(15) N1 0.211(36) 0.196(45) 0.051(27) -0.023(24) 0.008(23) 0.033(30) N2 0.047(12) 0.083(14) 0.070(13) -0.003(11) 0.025(11) -0.007(9) C1 0.185(31) 0.094(23) 0.032(19) -0.010(15) 0.018(17) 0.018(19) C2 0.116(21) 0.094(20) 0.053(17) -0.006(14) 0.043(15) -0.005(15) C3 0.085(17) 0.092(19) 0.036(14) -0.003(13) 0.043(12) -0.009(13) C4 0.013(8) 0.050(10) 0.014(8) -0.003(8) -0.004(7) 0.005(7) C5 0.089(17) 0.049(15) 0.071(17) 0.008(13) 0.054(14) -0.005(11) C6 0.124(21) 0.073(17) 0.024(14) 0.024(12) 0.017(12) 0.019(14) C7 0.144(29) 0.062(18) 0.066(17) -0.019(15) -0.010(16) -0.036(19) C8 0.155(30) 0.090(21) 0.181(30) -0.024(21) 0.113(26) -0.019(20) C9 0.111(26) 0.095(23) 0.257(44) 0.087(26) 0.076(28) 0.030(19) C10 0.143(23) 0.054(16) 0.045(14) 0.028(13) 0.027(15) 0.016(16) C11 0.182(35) 0.083(22) 0.127(26) -0.008(21) 0.017(25) 0.022(22) C12 0.275(50) 0.099(26) 0.209(40) -0.020(26) 0.155(38) 0.023(30) C13 0.051(19) 0.055(19) 0.053(18) 0.003(15) 0.011(15) 0.014(15) C14 0.071(18) 0.067(17) 0.037(16) -0.001(14) 0.026(14) 0.001(15) C15 0.070(19) 0.102(20) 0.075(18) 0.003(17) 0.037(15) 0.010(16) C16 0.065(19) 0.096(20) 0.064(18) -0.002(16) 0.040(15) 0.015(16) C17 0.047(13) 0.050(13) 0.034(13) 0.000(10) 0.024(10) 0.003(10) C18 0.087(18) 0.072(18) 0.052(16) -0.024(15) 0.041(14) 0.018(15) C19 0.084(20) 0.101(20) 0.104(20) -0.001(17) 0.028(16) 0.019(17) C20 0.066(19) 0.063(20) 0.046(17) -0.021(15) 0.032(15) 0.017(16) C21 0.085(38) 0.162(44) 0.104(41) -0.026(33) 0.015(31) -0.021(32) C22 0.136(35) 0.131(37) 0.051(24) -0.023(26) 0.061(25) -0.005(31) C23 0.134(42) 0.099(35) 0.106(34) -0.037(31) -0.009(30) 0.010(34) O4 0.127(24) 0.135(22) 0.060(18) 0.023(17) 0.053(17) 0.009(19) C24 0.057(31) 0.049(28) 0.060(29) 0.009(22) 0.008(26) 0.032(22) C25 0.054(18) 0.078(18) 0.058(18) -0.008(16) 0.029(15) -0.002(15) C26 0.102(20) 0.099(20) 0.094(20) -0.005(17) 0.041(16) 0.006(17) C27 0.078(18) 0.084(18) 0.069(18) -0.002(16) 0.010(15) 0.007(16) C28 0.062(17) 0.076(18) 0.048(16) 0.002(15) 0.034(14) -0.001(15) C29 0.099(22) 0.114(23) 0.097(21) 0.000(19) 0.020(17) 0.015(18) C30 0.096(20) 0.127(22) 0.103(20) -0.007(18) 0.048(16) 0.012(17) C31 0.080(20) 0.070(22) 0.067(19) 0.002(18) 0.010(16) 0.014(18) C32 0.055(29) 0.120(33) 0.026(23) -0.028(24) -0.012(22) 0.009(27) C33 0.083(30) 0.124(36) 0.112(34) -0.030(30) 0.039(26) 0.024(28) C34 0.107(37) 0.105(34) 0.101(34) -0.021(28) 0.026(29) -0.030(29) _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 O1 N1 1.13(4) . ? O2 N1 1.19(4) . ? O3 C13 1.24(2) . ? O3 O3 1.36(5) 2_656 ? N1 C1 1.39(3) . ? N2 C4 1.25 . ? N2 C13 1.306(12) . ? C1 C2 1.39 . ? C1 C6 1.39 . ? C2 C3 1.39 . ? C3 C4 1.39 . ? C3 C7 1.54(2) . ? C4 C5 1.39 . ? C5 C6 1.39 . ? C5 C10 1.52(2) . ? C7 C9 1.50(3) . ? C7 C8 1.51(3) . ? C10 C11 1.52(3) . ? C10 C12 1.52(3) . ? C13 C14 1.66 . ? C14 C15 1.39 . ? C14 C19 1.39 . ? C15 C16 1.39 . ? C16 C17 1.39 . ? C17 C18 1.39 . ? C17 C20 1.50(2) . ? C18 C19 1.39 . ? C20 C21 1.36(5) . ? C20 C22 1.53(5) . ? C20 C23 1.71(5) . ? O4 C24 1.21(2) . ? O4 O4 1.31(5) 5_756 ? C24 C25 1.77 . ? C25 C26 1.39 . ? C25 C30 1.39 . ? C26 C27 1.39 . ? C27 C28 1.39 . ? C28 C29 1.39 . ? C28 C31 1.51(2) . ? C29 C30 1.39 . ? C31 C34 1.40(5) . ? C31 C33 1.49(5) . ? C31 C32 1.69(5) . ? 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 C13 O3 O3 146.7(29) . 2_656 ? O1 N1 O2 115.1(37) . . ? O1 N1 C1 123.2(45) . . ? O2 N1 C1 120.4(44) . . ? C4 N2 C13 142.5(7) . . ? N1 C1 C2 118.7(24) . . ? N1 C1 C6 121.2(24) . . ? C2 C1 C6 120.0 . . ? C3 C2 C1 120.0 . . ? C2 C3 C4 120.0 . . ? C2 C3 C7 119.4(9) . . ? C4 C3 C7 120.5(9) . . ? N2 C4 C5 119.1 . . ? N2 C4 C3 120.7 . . ? C5 C4 C3 120.0 . . ? C6 C5 C4 120.0 . . ? C6 C5 C10 120.5(8) . . ? C4 C5 C10 119.5(9) . . ? C5 C6 C1 120.0 . . ? C9 C7 C8 112.3(19) . . ? C9 C7 C3 113.5(22) . . ? C8 C7 C3 109.3(19) . . ? C11 C10 C12 109.7(19) . . ? C11 C10 C5 110.5(19) . . ? C12 C10 C5 110.6(21) . . ? O3 C13 N2 110.0(16) . . ? O3 C13 C14 122.3(13) . . ? N2 C13 C14 125.5(8) . . ? C15 C14 C19 120.0 . . ? C15 C14 C13 110.9 . . ? C19 C14 C13 128.8 . . ? C14 C15 C16 120.0 . . ? C17 C16 C15 120.0 . . ? C16 C17 C18 120.0 . . ? C16 C17 C20 122.0(15) . . ? C18 C17 C20 118.0(15) . . ? C17 C18 C19 120.0 . . ? C18 C19 C14 120.0 . . ? C21 C20 C17 118.8(33) . . ? C21 C20 C22 116.1(32) . . ? C17 C20 C22 110.6(27) . . ? C21 C20 C23 106.2(31) . . ? C17 C20 C23 103.0(25) . . ? C22 C20 C23 99.1(28) . . ? C24 O4 O4 143.7(33) . 5_756 ? O4 C24 C25 105.8(16) . . ? C26 C25 C30 120.0 . . ? C26 C25 C24 115.5 . . ? C30 C25 C24 124.0 . . ? C25 C26 C27 120.0 . . ? C26 C27 C28 120.0 . . ? C27 C28 C29 120.0 . . ? C27 C28 C31 118.5(17) . . ? C29 C28 C31 121.4(17) . . ? C30 C29 C28 120.0 . . ? C29 C30 C25 120.0 . . ? C34 C31 C33 118.1(32) . . ? C34 C31 C28 114.4(31) . . ? C33 C31 C28 109.9(29) . . ? C34 C31 C32 105.0(31) . . ? C33 C31 C32 100.8(30) . . ? C28 C31 C32 106.9(26) . . ? _refine_diff_density_max 0.589 _refine_diff_density_min -0.576 _refine_diff_density_rms 0.097 data_gah16 _database_code_CSD 158586 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H33 N3 O' _chemical_formula_weight 367.52 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 15.567(7) _cell_length_b 19.117(10) _cell_length_c 15.266(6) _cell_angle_alpha 90.00 _cell_angle_beta 97.25(3) _cell_angle_gamma 90.00 _cell_volume 4507(4) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needles _exptl_crystal_colour colourless _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.083 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1600 _exptl_absorpt_coefficient_mu 0.067 _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 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 4519 _diffrn_reflns_av_R_equivalents 0.0552 _diffrn_reflns_av_sigmaI/netI 0.0770 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -1 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.06 _diffrn_reflns_theta_max 25.04 _reflns_number_total 3785 _reflns_number_gt 1557 _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^)+(0.1235P)^2^+9.2826P] 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 0.0017(6) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 3785 _refine_ls_number_parameters 322 _refine_ls_number_restraints 74 _refine_ls_R_factor_all 0.2078 _refine_ls_R_factor_gt 0.0977 _refine_ls_wR_factor_ref 0.3308 _refine_ls_wR_factor_gt 0.2459 _refine_ls_goodness_of_fit_ref 0.989 _refine_ls_restrained_S_all 0.985 _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 O1A O 0.7500 0.2500 0.0000 0.230(7) Uani 1.003(8) 2 d SP . 1 O1B O 0.9761(5) 0.2137(4) 0.2243(5) 0.094(3) Uani 0.498(4) 1 d P . 2 N1 N 0.8739(3) 0.2494(2) 0.1300(3) 0.0815(14) Uani 1 1 d . . . H1A H 0.9167 0.2291 0.1611 0.098 Uiso 0.502(4) 1 calc PR . 1 H1B H 0.8387 0.2358 0.0853 0.098 Uiso 0.498(4) 1 d PR . 2 N2 N 0.8194(4) 0.5315(3) 0.2145(4) 0.122(2) Uani 1 1 d . . . N3 N 0.8982(4) -0.0808(3) 0.0405(3) 0.1042(17) Uani 1 1 d . . . C1 C 0.8613(4) 0.3214(3) 0.1524(3) 0.0725(15) Uani 1 1 d . . . C2 C 0.9122(4) 0.3731(3) 0.1214(3) 0.0828(17) Uani 1 1 d . . . C3 C 0.8982(5) 0.4425(3) 0.1431(4) 0.0917(18) Uani 1 1 d . . . H3A H 0.9331 0.4770 0.1234 0.110 Uiso 1 1 calc R . . C4 C 0.8324(5) 0.4620(3) 0.1945(4) 0.0922(18) Uani 1 1 d . . . C5 C 0.7834(4) 0.4082(3) 0.2241(4) 0.0921(18) Uani 1 1 d . . . H5A H 0.7401 0.4193 0.2585 0.110 Uiso 1 1 calc R . . C6 C 0.7968(4) 0.3379(3) 0.2040(4) 0.0776(16) Uani 1 1 d . . . C7A C 0.8333(8) 0.2124(7) 0.0738(7) 0.093(5) Uani 0.502(4) 1 d P . 1 C7B C 0.9235(6) 0.2012(6) 0.1606(6) 0.072(3) Uani 0.498(4) 1 d P . 2 C8A C 0.8544(8) 0.1334(6) 0.0645(7) 0.061(2) Uani 0.502(4) 1 d PDU . 1 C8B C 0.9129(8) 0.1279(6) 0.1205(8) 0.062(2) Uani 0.498(4) 1 d PDU . 2 C9A C 0.9270(11) 0.1062(6) 0.1155(11) 0.090(2) Uani 0.502(4) 1 d PDU . 1 H9A H 0.9633 0.1351 0.1527 0.107 Uiso 0.502(4) 1 calc PR . 1 C9B C 0.8463(11) 0.1087(7) 0.0532(11) 0.091(2) Uani 0.498(4) 1 d PDU . 2 H9B H 0.8113 0.1439 0.0263 0.109 Uiso 0.498(4) 1 calc PR . 2 C10A C 0.9445(10) 0.0353(5) 0.1099(9) 0.090(2) Uani 0.502(4) 1 d PDU . 1 H10A H 0.9927 0.0174 0.1449 0.108 Uiso 0.502(4) 1 calc PR . 1 C10B C 0.8296(11) 0.0392(6) 0.0241(10) 0.092(2) Uani 0.498(4) 1 d PDU . 2 H10B H 0.7797 0.0270 -0.0128 0.110 Uiso 0.498(4) 1 calc PR . 2 C11 C 0.8937(4) -0.0104(3) 0.0548(3) 0.0831(16) Uani 1 1 d D . . C12A C 0.8279(10) 0.0230(6) 0.0000(10) 0.092(3) Uani 0.502(4) 1 d PDU . 1 H12A H 0.7984 -0.0039 -0.0448 0.111 Uiso 0.502(4) 1 calc PR . 1 C12B C 0.9618(9) 0.0080(5) 0.1218(9) 0.090(2) Uani 0.498(4) 1 d PDU . 2 H12B H 1.0005 -0.0266 0.1443 0.108 Uiso 0.498(4) 1 calc PR . 2 C13A C 0.8016(7) 0.0923(4) 0.0049(6) 0.081(3) Uani 0.502(4) 1 d PD . 1 H13A H 0.7525 0.1098 -0.0290 0.097 Uiso 0.502(4) 1 calc PR . 1 C13B C 0.9734(8) 0.0768(4) 0.1557(7) 0.084(3) Uani 0.498(4) 1 d PD . 2 H13B H 1.0187 0.0880 0.1992 0.100 Uiso 0.498(4) 1 calc PR . 2 C14 C 0.9817(4) 0.3548(3) 0.0620(4) 0.0964(19) Uani 1 1 d . . . H14A H 1.0025 0.3075 0.0777 0.116 Uiso 1 1 calc R . . C15 C 0.9401(5) 0.3530(5) -0.0355(4) 0.145(3) Uani 1 1 d . . . H15A H 0.8901 0.3232 -0.0410 0.218 Uiso 1 1 calc R . . H15B H 0.9813 0.3353 -0.0717 0.218 Uiso 1 1 calc R . . H15C H 0.9230 0.3995 -0.0542 0.218 Uiso 1 1 calc R . . C16 C 1.0595(5) 0.4029(4) 0.0717(5) 0.129(3) Uani 1 1 d . . . H16A H 1.0815 0.4073 0.1331 0.194 Uiso 1 1 calc R . . H16B H 1.0427 0.4481 0.0481 0.194 Uiso 1 1 calc R . . H16C H 1.1036 0.3837 0.0401 0.194 Uiso 1 1 calc R . . C17 C 0.7395(4) 0.2822(3) 0.2395(4) 0.0899(18) Uani 1 1 d . . . H17A H 0.7518 0.2401 0.2067 0.108 Uiso 1 1 calc R A 1 C18 C 0.6458(5) 0.2939(4) 0.2126(5) 0.139(3) Uani 1 1 d . . . H18A H 0.6280 0.3358 0.2399 0.209 Uiso 1 1 calc R . . H18B H 0.6137 0.2548 0.2309 0.209 Uiso 1 1 calc R . . H18C H 0.6350 0.2985 0.1496 0.209 Uiso 1 1 calc R . . C19A C 0.774(4) 0.266(3) 0.329(4) 0.129(12) Uani 0.502(4) 1 d PU . 1 H19A H 0.8354 0.2593 0.3326 0.193 Uiso 0.502(4) 1 calc PR . 1 H19B H 0.7477 0.2233 0.3466 0.193 Uiso 0.502(4) 1 calc PR . 1 H19C H 0.7614 0.3032 0.3671 0.193 Uiso 0.502(4) 1 calc PR . 1 C19B C 0.746(4) 0.285(3) 0.348(4) 0.128(12) Uani 0.498(4) 1 d PU . 2 H19D H 0.8047 0.2769 0.3729 0.191 Uiso 0.498(4) 1 calc PR . 2 H19E H 0.7096 0.2486 0.3674 0.191 Uiso 0.498(4) 1 calc PR . 2 H19F H 0.7268 0.3294 0.3658 0.191 Uiso 0.498(4) 1 calc PR . 2 C20 C 0.7571(7) 0.5487(4) 0.2723(6) 0.156(4) Uani 1 1 d . . . H20A H 0.7698 0.5232 0.3266 0.235 Uiso 1 1 calc R . . H20B H 0.7002 0.5366 0.2448 0.235 Uiso 1 1 calc R . . H20C H 0.7595 0.5980 0.2845 0.235 Uiso 1 1 calc R . . C21 C 0.8769(5) 0.5842(3) 0.1939(6) 0.141(3) Uani 1 1 d . . . H21A H 0.8579 0.6286 0.2137 0.212 Uiso 1 1 calc R . . H21B H 0.8779 0.5857 0.1311 0.212 Uiso 1 1 calc R . . H21C H 0.9340 0.5744 0.2228 0.212 Uiso 1 1 calc R . . C22 C 0.9683(5) -0.1214(4) 0.0822(5) 0.138(3) Uani 1 1 d . . . H22A H 0.9649 -0.1679 0.0582 0.206 Uiso 1 1 calc R . . H22B H 0.9652 -0.1234 0.1445 0.206 Uiso 1 1 calc R . . H22C H 1.0221 -0.1003 0.0719 0.206 Uiso 1 1 calc R . . C23 C 0.8412(6) -0.1132(4) -0.0290(5) 0.163(4) Uani 1 1 d . . . H23A H 0.8584 -0.1610 -0.0356 0.244 Uiso 1 1 calc R . . H23B H 0.8440 -0.0885 -0.0833 0.244 Uiso 1 1 calc R . . H23C H 0.7829 -0.1119 -0.0146 0.244 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 O1A 0.303(13) 0.174(8) 0.250(12) -0.144(9) 0.176(11) -0.132(9) O1B 0.108(7) 0.076(5) 0.082(6) -0.004(4) -0.044(4) 0.012(4) N1 0.093(3) 0.078(3) 0.065(3) -0.005(2) -0.023(3) 0.009(3) N2 0.191(6) 0.057(3) 0.130(5) -0.006(3) 0.065(5) 0.005(4) N3 0.134(5) 0.069(3) 0.103(4) -0.006(3) -0.010(3) 0.014(3) C1 0.091(4) 0.060(3) 0.061(3) -0.001(3) -0.014(3) 0.008(3) C2 0.112(5) 0.065(4) 0.067(3) 0.004(3) -0.004(3) 0.008(3) C3 0.120(5) 0.071(4) 0.083(4) 0.007(3) 0.011(4) -0.005(3) C4 0.127(5) 0.076(4) 0.076(4) 0.004(3) 0.019(4) 0.005(4) C5 0.121(5) 0.078(4) 0.079(4) -0.007(3) 0.019(4) -0.003(4) C6 0.094(4) 0.066(4) 0.069(3) 0.005(3) -0.005(3) 0.003(3) C7A 0.076(8) 0.137(12) 0.054(6) 0.033(7) -0.036(6) 0.011(8) C7B 0.059(6) 0.098(8) 0.052(6) 0.017(5) -0.021(5) 0.020(6) C8A 0.058(5) 0.082(6) 0.037(4) 0.003(5) -0.016(3) 0.007(5) C8B 0.058(5) 0.084(6) 0.037(4) 0.002(5) -0.017(3) 0.005(5) C9A 0.116(5) 0.072(4) 0.082(5) -0.001(4) 0.019(4) 0.022(4) C9B 0.116(5) 0.076(4) 0.082(5) 0.002(4) 0.021(4) 0.028(4) C10A 0.118(5) 0.071(5) 0.084(4) -0.005(5) 0.019(4) 0.017(5) C10B 0.119(4) 0.075(4) 0.085(5) 0.003(4) 0.024(4) 0.034(4) C11 0.105(4) 0.074(4) 0.070(3) -0.008(3) 0.010(3) -0.002(3) C12A 0.120(5) 0.075(5) 0.086(6) 0.002(4) 0.026(5) 0.036(5) C12B 0.120(6) 0.067(5) 0.085(5) -0.005(5) 0.018(4) 0.016(5) C13A 0.091(8) 0.094(8) 0.049(6) 0.006(5) -0.028(5) -0.006(7) C13B 0.101(9) 0.075(8) 0.070(7) -0.003(6) -0.010(6) 0.018(7) C14 0.104(5) 0.092(4) 0.098(5) 0.002(3) 0.028(4) 0.013(4) C15 0.160(7) 0.196(8) 0.085(5) -0.037(5) 0.034(5) -0.046(6) C16 0.099(5) 0.169(7) 0.119(6) -0.001(5) 0.013(4) 0.008(5) C17 0.103(5) 0.083(4) 0.081(4) -0.003(3) 0.000(3) -0.003(4) C18 0.122(6) 0.138(6) 0.157(7) 0.028(5) 0.018(5) 0.004(5) C19A 0.18(3) 0.13(3) 0.08(2) 0.028(15) 0.000(16) -0.03(2) C19B 0.18(3) 0.13(3) 0.07(2) 0.027(15) 0.002(16) -0.03(2) C20 0.243(10) 0.088(5) 0.161(7) -0.015(5) 0.109(8) 0.025(6) C21 0.171(8) 0.069(4) 0.183(8) -0.025(5) 0.020(6) -0.005(5) C22 0.153(7) 0.117(6) 0.148(7) 0.042(5) 0.041(6) 0.044(5) C23 0.214(9) 0.129(7) 0.137(7) -0.042(5) -0.010(7) -0.045(6) _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 O1A C7A 1.760(9) 7_655 ? O1A C7A 1.760(9) . ? O1B O1B 1.012(12) 2_755 ? O1B C7B 1.213(10) . ? N1 C7B 1.253(10) . ? N1 C7A 1.226(12) . ? N1 C1 1.437(6) . ? N2 C4 1.383(7) . ? N2 C21 1.410(8) . ? N2 C20 1.431(9) . ? N3 C11 1.366(7) . ? N3 C22 1.422(8) . ? N3 C23 1.437(8) . ? C1 C6 1.388(7) . ? C1 C2 1.387(7) . ? C2 C3 1.391(7) . ? C2 C14 1.537(8) . ? C3 C4 1.416(8) . ? C4 C5 1.390(8) . ? C5 C6 1.400(7) . ? C6 C17 1.531(8) . ? C7A C8A 1.555(17) . ? C7B C8B 1.531(15) . ? C8A C9A 1.390(6) . ? C8A C13A 1.390(6) . ? C8B C13B 1.414(6) . ? C8B C9B 1.412(6) . ? C9A C10A 1.388(6) . ? C9B C10B 1.413(6) . ? C10A C11 1.388(6) . ? C10B C11 1.413(6) . ? C11 C12B 1.421(6) . ? C11 C12A 1.394(6) . ? C12A C13A 1.392(6) . ? C12B C13B 1.418(6) . ? C14 C16 1.513(9) . ? C14 C15 1.546(8) . ? C17 C19A 1.44(6) . ? C17 C18 1.482(8) . ? C17 C19B 1.64(5) . ? 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 C7A O1A C7A 180.0(9) 7_655 . ? O1B O1B C7B 168.0(8) 2_755 . ? C7B N1 C7A 94.4(8) . . ? C7B N1 C1 135.3(6) . . ? C7A N1 C1 130.3(7) . . ? C4 N2 C21 121.5(6) . . ? C4 N2 C20 119.2(6) . . ? C21 N2 C20 118.1(6) . . ? C11 N3 C22 121.2(6) . . ? C11 N3 C23 120.3(6) . . ? C22 N3 C23 117.6(6) . . ? C6 C1 C2 121.2(5) . . ? C6 C1 N1 118.8(5) . . ? C2 C1 N1 120.0(5) . . ? C3 C2 C1 119.0(6) . . ? C3 C2 C14 120.1(6) . . ? C1 C2 C14 120.9(5) . . ? C2 C3 C4 122.0(6) . . ? N2 C4 C5 122.5(6) . . ? N2 C4 C3 120.8(6) . . ? C5 C4 C3 116.7(6) . . ? C4 C5 C6 122.4(6) . . ? C1 C6 C5 118.8(5) . . ? C1 C6 C17 122.6(5) . . ? C5 C6 C17 118.7(6) . . ? N1 C7A C8A 121.8(8) . . ? N1 C7A O1A 119.1(10) . . ? C8A C7A O1A 119.1(8) . . ? O1B C7B N1 118.4(10) . . ? O1B C7B C8B 121.9(8) . . ? N1 C7B C8B 119.6(7) . . ? C9A C8A C13A 121.8(12) . . ? C9A C8A C7A 118.6(8) . . ? C13A C8A C7A 119.5(9) . . ? C13B C8B C9B 119.3(12) . . ? C13B C8B C7B 116.5(8) . . ? C9B C8B C7B 124.2(9) . . ? C8A C9A C10A 118.8(12) . . ? C8B C9B C10B 124.2(12) . . ? C11 C10A C9A 123.5(10) . . ? C11 C10B C9B 115.6(11) . . ? N3 C11 C10B 131.0(7) . . ? N3 C11 C12B 108.1(6) . . ? C10B C11 C12B 120.2(8) . . ? N3 C11 C10A 132.8(6) . . ? C10B C11 C10A 95.9(8) . . ? C12B C11 C10A 24.8(6) . . ? N3 C11 C12A 113.8(7) . . ? C10B C11 C12A 19.7(9) . . ? C12B C11 C12A 138.1(8) . . ? C10A C11 C12A 113.2(9) . . ? C13A C12A C11 127.1(11) . . ? C13B C12B C11 122.8(9) . . ? C8A C13A C12A 114.8(11) . . ? C8B C13B C12B 117.0(10) . . ? C16 C14 C2 114.7(5) . . ? C16 C14 C15 109.9(6) . . ? C2 C14 C15 109.4(5) . . ? C19A C17 C18 122(2) . . ? C19A C17 C6 109(3) . . ? C18 C17 C6 113.3(5) . . ? C19A C17 C19B 24(3) . . ? C18 C17 C19B 102(2) . . ? C6 C17 C19B 112(2) . . ? 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 C7B N1 C1 C6 -96.4(10) . . . . ? C7A N1 C1 C6 78.9(10) . . . . ? C7B N1 C1 C2 84.7(10) . . . . ? C7A N1 C1 C2 -100.0(10) . . . . ? C6 C1 C2 C3 0.4(8) . . . . ? N1 C1 C2 C3 179.3(5) . . . . ? C6 C1 C2 C14 -178.1(5) . . . . ? N1 C1 C2 C14 0.8(7) . . . . ? C1 C2 C3 C4 -1.3(8) . . . . ? C14 C2 C3 C4 177.2(5) . . . . ? C21 N2 C4 C5 171.5(7) . . . . ? C20 N2 C4 C5 4.1(10) . . . . ? C21 N2 C4 C3 -7.6(10) . . . . ? C20 N2 C4 C3 -175.0(7) . . . . ? C2 C3 C4 N2 -179.4(6) . . . . ? C2 C3 C4 C5 1.4(9) . . . . ? N2 C4 C5 C6 -179.8(6) . . . . ? C3 C4 C5 C6 -0.6(9) . . . . ? C2 C1 C6 C5 0.3(8) . . . . ? N1 C1 C6 C5 -178.6(5) . . . . ? C2 C1 C6 C17 -179.9(5) . . . . ? N1 C1 C6 C17 1.2(7) . . . . ? C4 C5 C6 C1 -0.2(8) . . . . ? C4 C5 C6 C17 -180.0(5) . . . . ? C7B N1 C7A C8A 0.8(13) . . . . ? C1 N1 C7A C8A -175.9(9) . . . . ? C7B N1 C7A O1A -178.0(9) . . . . ? C1 N1 C7A O1A 5.3(15) . . . . ? C7A O1A C7A N1 -170(100) 7_655 . . . ? C7A O1A C7A C8A 11(100) 7_655 . . . ? O1B O1B C7B N1 -178(7) 2_755 . . . ? O1B O1B C7B C8B 6(8) 2_755 . . . ? C7A N1 C7B O1B -176.8(11) . . . . ? C1 N1 C7B O1B -0.4(16) . . . . ? C7A N1 C7B C8B -0.3(13) . . . . ? C1 N1 C7B C8B 176.1(9) . . . . ? N1 C7A C8A C9A -7(2) . . . . ? O1A C7A C8A C9A 172.0(15) . . . . ? N1 C7A C8A C13A 174.3(11) . . . . ? O1A C7A C8A C13A -6.9(17) . . . . ? O1B C7B C8B C13B -6.2(19) . . . . ? N1 C7B C8B C13B 177.4(10) . . . . ? O1B C7B C8B C9B 172.4(17) . . . . ? N1 C7B C8B C9B -4(2) . . . . ? C13A C8A C9A C10A -3(3) . . . . ? C7A C8A C9A C10A 177.7(15) . . . . ? C13B C8B C9B C10B 7(3) . . . . ? C7B C8B C9B C10B -171.4(16) . . . . ? C8A C9A C10A C11 1(3) . . . . ? C8B C9B C10B C11 -11(3) . . . . ? C22 N3 C11 C10B -177.0(12) . . . . ? C23 N3 C11 C10B 14.4(15) . . . . ? C22 N3 C11 C12B -6.5(11) . . . . ? C23 N3 C11 C12B -175.0(9) . . . . ? C22 N3 C11 C10A -4.4(15) . . . . ? C23 N3 C11 C10A -172.9(12) . . . . ? C22 N3 C11 C12A 171.5(10) . . . . ? C23 N3 C11 C12A 3.0(12) . . . . ? C9B C10B C11 N3 179.5(13) . . . . ? C9B C10B C11 C12B 10(2) . . . . ? C9B C10B C11 C10A 5(2) . . . . ? C9B C10B C11 C12A -148(6) . . . . ? C9A C10A C11 N3 -178.7(14) . . . . ? C9A C10A C11 C10B -4(2) . . . . ? C9A C10A C11 C12B -174(5) . . . . ? C9A C10A C11 C12A 5(2) . . . . ? N3 C11 C12A C13A 172.8(15) . . . . ? C10B C11 C12A C13A 19(3) . . . . ? C12B C11 C12A C13A -10(3) . . . . ? C10A C11 C12A C13A -10(2) . . . . ? N3 C11 C12B C13B -176.9(13) . . . . ? C10B C11 C12B C13B -5(2) . . . . ? C10A C11 C12B C13B 7(2) . . . . ? C12A C11 C12B C13B 6(3) . . . . ? C9A C8A C13A C12A -1(2) . . . . ? C7A C8A C13A C12A 178.1(15) . . . . ? C11 C12A C13A C8A 8(2) . . . . ? C9B C8B C13B C12B -1(2) . . . . ? C7B C8B C13B C12B 177.3(14) . . . . ? C11 C12B C13B C8B 1(2) . . . . ? C3 C2 C14 C16 32.3(8) . . . . ? C1 C2 C14 C16 -149.2(6) . . . . ? C3 C2 C14 C15 -91.7(7) . . . . ? C1 C2 C14 C15 86.8(7) . . . . ? C1 C6 C17 C19A 97.5(18) . . . . ? C5 C6 C17 C19A -82.7(18) . . . . ? C1 C6 C17 C18 -123.0(6) . . . . ? C5 C6 C17 C18 56.7(7) . . . . ? C1 C6 C17 C19B 122(2) . . . . ? C5 C6 C17 C19B -58(2) . . . . ? _diffrn_measured_fraction_theta_max 0.947 _diffrn_reflns_theta_full 25.04 _diffrn_measured_fraction_theta_full 0.947 _refine_diff_density_max 0.378 _refine_diff_density_min -0.293 _refine_diff_density_rms 0.042 data_gah17 _database_code_CSD 158587 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common 'N-4 dimethylamino 2,6 diisopropylphenyl 4 t-butylbenzamide' _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C25 H36 N2 O' _chemical_formula_weight 380.56 _chemical_melting_point ? _chemical_compound_source ? 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/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.539(2) _cell_length_b 10.092(2) _cell_length_c 25.400(5) _cell_angle_alpha 90.00 _cell_angle_beta 99.911(4) _cell_angle_gamma 90.00 _cell_volume 2408.7(8) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 1.80 _exptl_crystal_size_mid 0.02 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.049 _exptl_crystal_density_method ? _exptl_crystal_F_000 832 _exptl_absorpt_coefficient_mu 0.063 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Rigaku R-Axis' _diffrn_measurement_method 'Image plate scans' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9063 _diffrn_reflns_av_R_equivalents 0.0643 _diffrn_reflns_av_sigmaI/netI 0.2402 _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 -30 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 2.18 _diffrn_reflns_theta_max 25.24 _reflns_number_total 3663 _reflns_number_observed 1158 _reflns_observed_criterion >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0759P)^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 ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3663 _refine_ls_number_parameters 253 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1979 _refine_ls_R_factor_obs 0.0690 _refine_ls_wR_factor_all 0.1996 _refine_ls_wR_factor_obs 0.1677 _refine_ls_goodness_of_fit_all 0.725 _refine_ls_goodness_of_fit_obs 1.156 _refine_ls_restrained_S_all 0.725 _refine_ls_restrained_S_obs 1.156 _refine_ls_shift/esd_max 0.054 _refine_ls_shift/esd_mean 0.003 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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group O1 O 0.2571(4) 0.3415(3) 0.75460(13) 0.0865(13) Uani 1 d . . N1 N -0.1463(5) 0.1567(5) 0.5407(2) 0.093(2) Uani 1 d . . N2 N 0.2082(4) 0.1260(3) 0.74126(13) 0.0532(11) Uani 1 d . . H2 H 0.2165(4) 0.0479(3) 0.75501(13) 0.064 Uiso 1 calc R . C1 C -0.0593(5) 0.1545(4) 0.5905(2) 0.0576(13) Uani 1 d . . C2 C -0.1156(5) 0.1511(4) 0.6375(2) 0.0584(13) Uani 1 d . . H2A H -0.2139(5) 0.1524(4) 0.6352(2) 0.070 Uiso 1 calc R . C3 C -0.0297(5) 0.1460(4) 0.6878(2) 0.0524(12) Uani 1 d . . C4 C 0.1176(5) 0.1442(4) 0.6908(2) 0.0465(12) Uani 1 d . . C5 C 0.1773(5) 0.1490(4) 0.6447(2) 0.0545(13) Uani 1 d . . C6 C 0.0886(5) 0.1560(4) 0.5949(2) 0.0641(14) Uani 1 d . . H6 H 0.1289(5) 0.1619(4) 0.5641(2) 0.077 Uiso 1 calc R . C7 C -0.0890(6) 0.1785(5) 0.4926(2) 0.089(2) Uani 1 d . . H7A H -0.1647(6) 0.1767(5) 0.4624(2) 0.107 Uiso 1 calc R . H7B H -0.0214(6) 0.1101(5) 0.4889(2) 0.107 Uiso 1 calc R . H7C H -0.0426(6) 0.2632(5) 0.4945(2) 0.107 Uiso 1 calc R . C8 C -0.2966(5) 0.1342(5) 0.5365(2) 0.090(2) Uani 1 d . . H8A H -0.3412(5) 0.1390(5) 0.4996(2) 0.107 Uiso 1 calc R . H8B H -0.3367(5) 0.2005(5) 0.5566(2) 0.107 Uiso 1 calc R . H8C H -0.3124(5) 0.0480(5) 0.5504(2) 0.107 Uiso 1 calc R . C9 C -0.0921(6) 0.1441(6) 0.7378(2) 0.080(2) Uani 1 d . . H9 H -0.0209(6) 0.1011(6) 0.7648(2) 0.096 Uiso 1 calc R . C12 C 0.3368(5) 0.1457(6) 0.6466(2) 0.075(2) Uani 1 d . . H12 H 0.3799(5) 0.1369(6) 0.6843(2) 0.090 Uiso 1 calc R . C13 C 0.3832(6) 0.0265(7) 0.6186(3) 0.140(3) Uani 1 d . . H13A H 0.3451(6) -0.0521(7) 0.6320(3) 0.168 Uiso 1 calc R . H13B H 0.4852(6) 0.0217(7) 0.6249(3) 0.168 Uiso 1 calc R . H13C H 0.3489(6) 0.0338(7) 0.5809(3) 0.168 Uiso 1 calc R . C14 C 0.3927(6) 0.2726(6) 0.6274(3) 0.125(3) Uani 1 d . . H14A H 0.3606(6) 0.3458(6) 0.6464(3) 0.150 Uiso 1 calc R . H14B H 0.3584(6) 0.2827(6) 0.5898(3) 0.150 Uiso 1 calc R . H14C H 0.4948(6) 0.2705(6) 0.6339(3) 0.150 Uiso 1 calc R . C15 C 0.2810(5) 0.2262(4) 0.7680(2) 0.0558(14) Uani 1 d . . C16 C 0.3953(5) 0.1913(4) 0.8137(2) 0.0519(13) Uani 1 d . . C17 C 0.4748(5) 0.2915(4) 0.8405(2) 0.067(2) Uani 1 d . . H17 H 0.4490(5) 0.3790(4) 0.8324(2) 0.080 Uiso 1 calc R . C18 C 0.5915(5) 0.2659(4) 0.8791(2) 0.067(2) Uani 1 d . . H18 H 0.6438(5) 0.3366(4) 0.8958(2) 0.080 Uiso 1 calc R . C19 C 0.6330(5) 0.1397(4) 0.8936(2) 0.0616(14) Uani 1 d . . C20 C 0.5501(6) 0.0391(4) 0.8679(2) 0.089(2) Uani 1 d . . H20 H 0.5735(6) -0.0481(4) 0.8775(2) 0.106 Uiso 1 calc R . C21 C 0.4337(5) 0.0627(4) 0.8286(2) 0.078(2) Uani 1 d . . H21 H 0.3809(5) -0.0080(4) 0.8122(2) 0.094 Uiso 1 calc R . C22 C 0.7668(6) 0.1082(5) 0.9345(2) 0.085(2) Uani 1 d . . C23 C 0.8621(7) 0.0198(7) 0.9103(3) 0.155(3) Uani 1 d . . H23A H 0.8092(7) -0.0555(7) 0.8946(3) 0.186 Uiso 1 calc R . H23B H 0.9385(7) -0.0097(7) 0.9375(3) 0.186 Uiso 1 calc R . H23C H 0.9004(7) 0.0672(7) 0.8833(3) 0.186 Uiso 1 calc R . C24 C 0.8381(6) 0.2290(5) 0.9603(3) 0.127(3) Uani 1 d . . H24A H 0.7702(6) 0.2812(5) 0.9750(3) 0.153 Uiso 1 calc R . H24B H 0.8760(6) 0.2802(5) 0.9341(3) 0.153 Uiso 1 calc R . H24C H 0.9140(6) 0.2032(5) 0.9883(3) 0.153 Uiso 1 calc R . C25 C 0.7185(7) 0.0270(6) 0.9820(3) 0.136(3) Uani 1 d . . H25A H 0.6562(7) 0.0807(6) 0.9990(3) 0.163 Uiso 1 calc R . H25B H 0.8009(7) 0.0034(6) 1.0077(3) 0.163 Uiso 1 calc R . H25C H 0.6695(7) -0.0519(6) 0.9681(3) 0.163 Uiso 1 calc R . C26 C -0.2138(16) 0.0782(15) 0.7381(4) 0.423(14) Uani 1 d . . H26A H -0.2062(16) -0.0094(15) 0.7242(4) 0.507 Uiso 1 calc R . H26B H -0.2908(16) 0.1243(15) 0.7164(4) 0.507 Uiso 1 calc R . H26C H -0.2318(16) 0.0725(15) 0.7741(4) 0.507 Uiso 1 calc R . C27 C -0.1166(15) 0.2716(10) 0.7590(5) 0.336(10) Uani 1 d . . H27A H -0.0329(15) 0.3252(10) 0.7606(5) 0.404 Uiso 1 calc R . H27B H -0.1384(15) 0.2615(10) 0.7944(5) 0.404 Uiso 1 calc R . H27C H -0.1951(15) 0.3136(10) 0.7365(5) 0.404 Uiso 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 O1 0.116(3) 0.034(2) 0.087(3) 0.004(2) -0.048(2) 0.003(2) N1 0.058(3) 0.154(4) 0.056(3) 0.013(3) -0.017(3) -0.011(3) N2 0.061(3) 0.034(2) 0.054(2) 0.005(2) -0.018(2) -0.005(2) C1 0.051(3) 0.061(3) 0.055(3) 0.003(3) -0.009(3) 0.001(2) C2 0.042(3) 0.059(3) 0.068(4) 0.006(3) -0.009(3) -0.004(2) C3 0.056(3) 0.042(2) 0.057(3) 0.002(2) 0.003(3) 0.000(2) C4 0.046(3) 0.035(2) 0.052(3) 0.002(2) -0.009(2) -0.003(2) C5 0.045(3) 0.051(3) 0.060(3) 0.001(2) -0.014(3) -0.003(2) C6 0.057(3) 0.082(3) 0.051(3) 0.005(3) 0.000(3) -0.007(3) C7 0.091(4) 0.108(4) 0.059(4) 0.005(3) -0.014(3) 0.001(3) C8 0.067(4) 0.109(4) 0.081(4) -0.006(3) -0.024(3) 0.005(3) C9 0.073(4) 0.100(4) 0.067(4) 0.005(3) 0.009(3) 0.006(3) C12 0.053(3) 0.099(4) 0.068(4) 0.000(3) -0.003(3) -0.008(3) C13 0.063(5) 0.163(7) 0.191(8) -0.042(6) 0.016(5) 0.009(4) C14 0.072(5) 0.134(6) 0.162(7) 0.013(5) 0.003(4) -0.031(4) C15 0.068(3) 0.039(2) 0.052(3) -0.002(2) -0.014(3) 0.004(2) C16 0.061(3) 0.036(2) 0.050(3) -0.003(2) -0.015(2) 0.004(2) C17 0.077(4) 0.037(2) 0.073(3) -0.006(2) -0.026(3) 0.002(2) C18 0.074(4) 0.044(2) 0.069(3) -0.010(2) -0.027(3) -0.001(2) C19 0.061(3) 0.054(3) 0.059(3) 0.000(2) -0.019(3) 0.012(3) C20 0.100(4) 0.044(3) 0.097(4) 0.001(3) -0.054(4) 0.011(3) C21 0.095(4) 0.039(2) 0.080(4) -0.001(2) -0.044(3) -0.002(3) C22 0.081(4) 0.065(3) 0.090(4) -0.008(3) -0.037(4) 0.016(3) C23 0.110(6) 0.189(7) 0.141(7) -0.049(6) -0.047(5) 0.076(6) C24 0.105(5) 0.102(4) 0.142(6) -0.012(4) -0.073(5) -0.003(4) C25 0.147(6) 0.118(5) 0.115(6) 0.034(4) -0.059(5) -0.008(5) C26 0.581(26) 0.606(27) 0.153(10) -0.181(13) 0.265(14) -0.477(24) C27 0.609(28) 0.163(10) 0.330(17) 0.010(9) 0.341(19) 0.098(13) _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 O1 C15 1.223(4) . ? N1 C1 1.388(6) . ? N1 C7 1.437(6) . ? N1 C8 1.438(6) . ? N2 C15 1.343(5) . ? N2 C4 1.428(5) . ? C1 C2 1.391(6) . ? C1 C6 1.396(6) . ? C2 C3 1.396(6) . ? C3 C4 1.394(6) . ? C3 C9 1.492(7) . ? C4 C5 1.389(6) . ? C5 C6 1.398(6) . ? C5 C12 1.515(6) . ? C9 C26 1.340(10) . ? C9 C27 1.430(9) . ? C12 C14 1.500(7) . ? C12 C13 1.502(7) . ? C15 C16 1.490(5) . ? C16 C17 1.373(5) . ? C16 C21 1.384(5) . ? C17 C18 1.375(5) . ? C18 C19 1.366(5) . ? C19 C20 1.380(6) . ? C19 C22 1.534(6) . ? C20 C21 1.380(6) . ? C22 C23 1.480(8) . ? C22 C24 1.491(6) . ? C22 C25 1.592(8) . ? 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 C1 N1 C7 121.4(5) . . ? C1 N1 C8 119.8(5) . . ? C7 N1 C8 118.8(4) . . ? C15 N2 C4 122.5(3) . . ? N1 C1 C2 121.6(5) . . ? N1 C1 C6 120.6(5) . . ? C2 C1 C6 117.8(4) . . ? C1 C2 C3 122.3(4) . . ? C4 C3 C2 118.6(5) . . ? C4 C3 C9 119.9(4) . . ? C2 C3 C9 121.5(5) . . ? C5 C4 C3 120.5(4) . . ? C5 C4 N2 119.3(4) . . ? C3 C4 N2 120.0(4) . . ? C4 C5 C6 119.6(4) . . ? C4 C5 C12 121.9(4) . . ? C6 C5 C12 118.5(5) . . ? C1 C6 C5 121.1(5) . . ? C26 C9 C27 104.2(9) . . ? C26 C9 C3 119.1(6) . . ? C27 C9 C3 115.2(6) . . ? C14 C12 C13 112.4(6) . . ? C14 C12 C5 112.5(5) . . ? C13 C12 C5 112.3(4) . . ? O1 C15 N2 121.3(4) . . ? O1 C15 C16 121.2(4) . . ? N2 C15 C16 117.4(3) . . ? C17 C16 C21 117.2(4) . . ? C17 C16 C15 118.7(3) . . ? C21 C16 C15 124.0(3) . . ? C16 C17 C18 121.7(4) . . ? C19 C18 C17 121.9(4) . . ? C18 C19 C20 116.3(4) . . ? C18 C19 C22 123.0(4) . . ? C20 C19 C22 120.7(4) . . ? C19 C20 C21 122.6(4) . . ? C20 C21 C16 120.2(4) . . ? C23 C22 C24 114.1(6) . . ? C23 C22 C19 110.1(5) . . ? C24 C22 C19 113.1(4) . . ? C23 C22 C25 106.4(5) . . ? C24 C22 C25 104.8(5) . . ? C19 C22 C25 107.7(5) . . ? _refine_diff_density_max 0.411 _refine_diff_density_min -0.263 _refine_diff_density_rms 0.039 data_gah19 _database_code_CSD 158588 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H28 N2 O' _chemical_formula_weight 324.45 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 23.289(4) _cell_length_b 9.9638(15) _cell_length_c 17.896(3) _cell_angle_alpha 90.00 _cell_angle_beta 113.020(3) _cell_angle_gamma 90.00 _cell_volume 3822.0(10) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 43 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description BLOCK _exptl_crystal_colour COLOURLESS _exptl_crystal_size_max 0.41 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.128 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1408 _exptl_absorpt_coefficient_mu 0.069 _exptl_absorpt_correction_type semi-empirical _exptl_absorpt_correction_T_min 0.9722 _exptl_absorpt_correction_T_max 0.9876 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11862 _diffrn_reflns_av_R_equivalents 0.0767 _diffrn_reflns_av_sigmaI/netI 0.0831 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 30 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.25 _diffrn_reflns_theta_max 28.30 _reflns_number_total 4610 _reflns_number_gt 2523 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.1199P)^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 4610 _refine_ls_number_parameters 217 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1271 _refine_ls_R_factor_gt 0.0705 _refine_ls_wR_factor_ref 0.2167 _refine_ls_wR_factor_gt 0.1887 _refine_ls_goodness_of_fit_ref 0.950 _refine_ls_restrained_S_all 0.950 _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 N1 N 0.24516(9) 0.49944(17) 0.24161(11) 0.0284(4) Uani 1 1 d . . . H1A H 0.2609 0.4179 0.2516 0.034 Uiso 1 1 calc R . . N2 N 0.47248(11) 0.4856(2) 0.59473(13) 0.0494(6) Uani 1 1 d . . . O1 O 0.25667(8) 0.71810(15) 0.27691(10) 0.0389(4) Uani 1 1 d . . . C1 C 0.27467(10) 0.6007(2) 0.29251(13) 0.0284(5) Uani 1 1 d . . . C2 C 0.32845(10) 0.5648(2) 0.36810(13) 0.0268(5) Uani 1 1 d . . . C3 C 0.36408(11) 0.6681(2) 0.41665(13) 0.0320(5) Uani 1 1 d . . . H3A H 0.3550 0.7581 0.3983 0.038 Uiso 1 1 calc R . . C4 C 0.41177(11) 0.6441(2) 0.48987(14) 0.0359(6) Uani 1 1 d . . . H4A H 0.4355 0.7171 0.5208 0.043 Uiso 1 1 calc R . . C5 C 0.42601(11) 0.5128(2) 0.51983(14) 0.0347(5) Uani 1 1 d . . . C6 C 0.39027(12) 0.4078(2) 0.47086(14) 0.0363(6) Uani 1 1 d . . . H6A H 0.3991 0.3177 0.4891 0.044 Uiso 1 1 calc R . . C7 C 0.34298(11) 0.4336(2) 0.39729(14) 0.0329(5) Uani 1 1 d . . . H7A H 0.3196 0.3609 0.3655 0.039 Uiso 1 1 calc R . . C8 C 0.18895(10) 0.5221(2) 0.17197(13) 0.0281(5) Uani 1 1 d . . . C9 C 0.19156(12) 0.5188(2) 0.09515(14) 0.0345(6) Uani 1 1 d . . . C10 C 0.13551(13) 0.5372(2) 0.02829(14) 0.0405(6) Uani 1 1 d . . . H10A H 0.1357 0.5369 -0.0247 0.049 Uiso 1 1 calc R . . C11 C 0.08028(13) 0.5556(2) 0.03733(15) 0.0410(6) Uani 1 1 d . . . H11A H 0.0427 0.5674 -0.0092 0.049 Uiso 1 1 calc R . . C12 C 0.07892(12) 0.5570(2) 0.11392(14) 0.0392(6) Uani 1 1 d . . . H12A H 0.0404 0.5704 0.1195 0.047 Uiso 1 1 calc R . . C13 C 0.13334(11) 0.5392(2) 0.18300(13) 0.0311(5) Uani 1 1 d . . . C14 C 0.13041(12) 0.5328(2) 0.26632(14) 0.0377(6) Uani 1 1 d . . . H14A H 0.1741 0.5222 0.3072 0.045 Uiso 1 1 calc R . . C15 C 0.09405(16) 0.4094(3) 0.27256(18) 0.0617(9) Uani 1 1 d . . . H15A H 0.1124 0.3291 0.2591 0.093 Uiso 1 1 calc R . . H15B H 0.0505 0.4180 0.2345 0.093 Uiso 1 1 calc R . . H15C H 0.0959 0.4016 0.3280 0.093 Uiso 1 1 calc R . . C16 C 0.10469(16) 0.6613(3) 0.28676(19) 0.0650(9) Uani 1 1 d . . . H16A H 0.1298 0.7377 0.2827 0.098 Uiso 1 1 calc R . . H16B H 0.1063 0.6557 0.3422 0.098 Uiso 1 1 calc R . . H16C H 0.0614 0.6737 0.2486 0.098 Uiso 1 1 calc R . . C17 C 0.25258(13) 0.4966(3) 0.08620(16) 0.0468(7) Uani 1 1 d . . . H17A H 0.2762 0.4271 0.1270 0.056 Uiso 1 1 calc R . . C18 C 0.29194(16) 0.6240(4) 0.10625(19) 0.0686(10) Uani 1 1 d . . . H18A H 0.2965 0.6569 0.1599 0.103 Uiso 1 1 calc R . . H18B H 0.2714 0.6928 0.0653 0.103 Uiso 1 1 calc R . . H18C H 0.3332 0.6044 0.1064 0.103 Uiso 1 1 calc R . . C19 C 0.24476(16) 0.4437(3) 0.00282(18) 0.0632(9) Uani 1 1 d . . . H19A H 0.2194 0.3619 -0.0092 0.095 Uiso 1 1 calc R . . H19B H 0.2858 0.4235 0.0025 0.095 Uiso 1 1 calc R . . H19C H 0.2240 0.5119 -0.0384 0.095 Uiso 1 1 calc R . . C20 C 0.48617(14) 0.3495(3) 0.62392(16) 0.0535(8) Uani 1 1 d . . . H20A H 0.4573 0.2879 0.5841 0.080 Uiso 1 1 calc R . . H20B H 0.4814 0.3409 0.6757 0.080 Uiso 1 1 calc R . . H20C H 0.5291 0.3272 0.6317 0.080 Uiso 1 1 calc R . . C21 C 0.50872(13) 0.5943(3) 0.64371(15) 0.0484(7) Uani 1 1 d . . . H21A H 0.4938 0.6796 0.6155 0.073 Uiso 1 1 calc R . . H21B H 0.5527 0.5819 0.6530 0.073 Uiso 1 1 calc R . . H21C H 0.5043 0.5953 0.6960 0.073 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 N1 0.0307(11) 0.0244(9) 0.0272(10) 0.0016(7) 0.0083(8) 0.0017(7) N2 0.0514(15) 0.0450(13) 0.0343(12) 0.0009(10) -0.0022(11) 0.0045(10) O1 0.0436(11) 0.0256(9) 0.0371(9) 0.0016(7) 0.0045(8) 0.0016(7) C1 0.0331(13) 0.0274(11) 0.0260(11) 0.0015(9) 0.0130(10) -0.0029(9) C2 0.0275(12) 0.0278(11) 0.0262(11) 0.0007(9) 0.0115(10) 0.0002(8) C3 0.0356(14) 0.0273(11) 0.0325(12) 0.0011(9) 0.0129(11) -0.0004(9) C4 0.0367(14) 0.0360(13) 0.0305(12) -0.0051(10) 0.0082(11) -0.0048(10) C5 0.0347(14) 0.0401(13) 0.0263(12) 0.0019(10) 0.0085(11) 0.0034(10) C6 0.0428(15) 0.0300(12) 0.0357(13) 0.0052(10) 0.0148(12) 0.0071(10) C7 0.0364(14) 0.0300(12) 0.0309(12) -0.0022(9) 0.0118(11) -0.0005(9) C8 0.0321(13) 0.0218(11) 0.0261(11) 0.0003(8) 0.0068(10) -0.0021(8) C9 0.0476(15) 0.0275(12) 0.0291(12) -0.0007(9) 0.0156(11) -0.0033(10) C10 0.0530(17) 0.0389(14) 0.0248(12) 0.0020(10) 0.0099(12) -0.0052(11) C11 0.0417(16) 0.0377(13) 0.0301(13) 0.0026(10) -0.0007(11) -0.0042(11) C12 0.0323(14) 0.0424(14) 0.0368(14) -0.0003(11) 0.0068(11) -0.0007(10) C13 0.0334(13) 0.0271(11) 0.0294(12) -0.0001(9) 0.0088(10) -0.0034(9) C14 0.0335(14) 0.0493(15) 0.0293(12) 0.0014(11) 0.0114(11) 0.0000(11) C15 0.067(2) 0.077(2) 0.0433(16) 0.0066(15) 0.0236(16) -0.0160(16) C16 0.079(2) 0.073(2) 0.0486(17) -0.0055(15) 0.0301(17) 0.0177(17) C17 0.0501(17) 0.0577(16) 0.0374(14) 0.0013(12) 0.0224(13) -0.0014(13) C18 0.068(2) 0.095(3) 0.0558(19) -0.0164(18) 0.0373(18) -0.0323(19) C19 0.074(2) 0.080(2) 0.0497(17) -0.0097(16) 0.0393(17) -0.0050(17) C20 0.0537(18) 0.0568(18) 0.0368(15) 0.0095(13) 0.0034(13) 0.0070(13) C21 0.0479(17) 0.0571(17) 0.0311(13) -0.0028(12) 0.0058(12) -0.0006(13) _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 N1 C1 1.353(3) . ? N1 C8 1.429(3) . ? N2 C5 1.381(3) . ? N2 C21 1.441(3) . ? N2 C20 1.444(3) . ? O1 C1 1.237(3) . ? C1 C2 1.484(3) . ? C2 C3 1.393(3) . ? C2 C7 1.400(3) . ? C3 C4 1.367(3) . ? C4 C5 1.404(3) . ? C5 C6 1.408(3) . ? C6 C7 1.370(3) . ? C8 C13 1.395(3) . ? C8 C9 1.400(3) . ? C9 C10 1.396(3) . ? C9 C17 1.507(4) . ? C10 C11 1.370(4) . ? C11 C12 1.383(3) . ? C12 C13 1.393(3) . ? C13 C14 1.520(3) . ? C14 C16 1.518(4) . ? C14 C15 1.521(4) . ? C17 C18 1.525(4) . ? C17 C19 1.525(4) . ? 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 C1 N1 C8 121.34(18) . . ? C5 N2 C21 119.6(2) . . ? C5 N2 C20 120.9(2) . . ? C21 N2 C20 119.5(2) . . ? O1 C1 N1 121.0(2) . . ? O1 C1 C2 121.62(19) . . ? N1 C1 C2 117.35(18) . . ? C3 C2 C7 117.4(2) . . ? C3 C2 C1 118.37(19) . . ? C7 C2 C1 124.1(2) . . ? C4 C3 C2 122.1(2) . . ? C3 C4 C5 120.8(2) . . ? N2 C5 C4 122.1(2) . . ? N2 C5 C6 120.4(2) . . ? C4 C5 C6 117.4(2) . . ? C7 C6 C5 121.1(2) . . ? C6 C7 C2 121.3(2) . . ? C13 C8 C9 122.8(2) . . ? C13 C8 N1 118.72(19) . . ? C9 C8 N1 118.4(2) . . ? C10 C9 C8 117.0(2) . . ? C10 C9 C17 122.2(2) . . ? C8 C9 C17 120.8(2) . . ? C11 C10 C9 121.5(2) . . ? C10 C11 C12 120.3(2) . . ? C11 C12 C13 120.8(2) . . ? C12 C13 C8 117.6(2) . . ? C12 C13 C14 120.1(2) . . ? C8 C13 C14 122.3(2) . . ? C16 C14 C13 112.0(2) . . ? C16 C14 C15 112.4(3) . . ? C13 C14 C15 110.2(2) . . ? C9 C17 C18 111.0(2) . . ? C9 C17 C19 113.5(2) . . ? C18 C17 C19 110.4(2) . . ? 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 C8 N1 C1 O1 -5.8(3) . . . . ? C8 N1 C1 C2 173.09(18) . . . . ? O1 C1 C2 C3 -8.6(3) . . . . ? N1 C1 C2 C3 172.5(2) . . . . ? O1 C1 C2 C7 166.2(2) . . . . ? N1 C1 C2 C7 -12.7(3) . . . . ? C7 C2 C3 C4 0.4(3) . . . . ? C1 C2 C3 C4 175.5(2) . . . . ? C2 C3 C4 C5 -1.2(4) . . . . ? C21 N2 C5 C4 -1.2(4) . . . . ? C20 N2 C5 C4 -179.9(2) . . . . ? C21 N2 C5 C6 179.7(2) . . . . ? C20 N2 C5 C6 1.0(4) . . . . ? C3 C4 C5 N2 -177.8(2) . . . . ? C3 C4 C5 C6 1.3(4) . . . . ? N2 C5 C6 C7 178.4(2) . . . . ? C4 C5 C6 C7 -0.8(4) . . . . ? C5 C6 C7 C2 0.0(4) . . . . ? C3 C2 C7 C6 0.2(3) . . . . ? C1 C2 C7 C6 -174.6(2) . . . . ? C1 N1 C8 C13 -76.0(3) . . . . ? C1 N1 C8 C9 107.5(2) . . . . ? C13 C8 C9 C10 1.7(3) . . . . ? N1 C8 C9 C10 178.06(19) . . . . ? C13 C8 C9 C17 -178.4(2) . . . . ? N1 C8 C9 C17 -2.1(3) . . . . ? C8 C9 C10 C11 -1.0(3) . . . . ? C17 C9 C10 C11 179.1(2) . . . . ? C9 C10 C11 C12 0.3(4) . . . . ? C10 C11 C12 C13 -0.4(4) . . . . ? C11 C12 C13 C8 1.0(3) . . . . ? C11 C12 C13 C14 -176.4(2) . . . . ? C9 C8 C13 C12 -1.7(3) . . . . ? N1 C8 C13 C12 -178.08(19) . . . . ? C9 C8 C13 C14 175.6(2) . . . . ? N1 C8 C13 C14 -0.8(3) . . . . ? C12 C13 C14 C16 -61.0(3) . . . . ? C8 C13 C14 C16 121.8(3) . . . . ? C12 C13 C14 C15 64.9(3) . . . . ? C8 C13 C14 C15 -112.3(3) . . . . ? C10 C9 C17 C18 102.9(3) . . . . ? C8 C9 C17 C18 -77.0(3) . . . . ? C10 C9 C17 C19 -22.0(3) . . . . ? C8 C9 C17 C19 158.1(2) . . . . ? _diffrn_measured_fraction_theta_max 0.970 _diffrn_reflns_theta_full 28.30 _diffrn_measured_fraction_theta_full 0.970 _refine_diff_density_max 0.421 _refine_diff_density_min -0.397 _refine_diff_density_rms 0.061 data_gah20 _database_code_CSD 158589 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common 'N-4 nitro 2,6 diisopropylphenyl 4 dimethyl aminobenzamide' _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C21 H27 N3 O3' _chemical_formula_weight 369.46 _chemical_melting_point ? _chemical_compound_source ? 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 13.062(5) _cell_length_b 10.059(4) _cell_length_c 16.675(5) _cell_angle_alpha 90.00 _cell_angle_beta 112.86(2) _cell_angle_gamma 90.00 _cell_volume 2018.9(13) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needles _exptl_crystal_colour yellow _exptl_crystal_size_max 0.8 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.216 _exptl_crystal_density_method ? _exptl_crystal_F_000 792 _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _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 ? _diffrn_measurement_method ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4538 _diffrn_reflns_av_R_equivalents 0.0394 _diffrn_reflns_av_sigmaI/netI 0.0627 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -1 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.42 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3551 _reflns_number_observed 1828 _reflns_observed_criterion >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0849P)^2^+0.6954P] 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 ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3551 _refine_ls_number_parameters 254 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.1355 _refine_ls_R_factor_obs 0.0663 _refine_ls_wR_factor_all 0.2065 _refine_ls_wR_factor_obs 0.1607 _refine_ls_goodness_of_fit_all 1.013 _refine_ls_goodness_of_fit_obs 1.130 _refine_ls_restrained_S_all 1.013 _refine_ls_restrained_S_obs 1.128 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group O1 O 0.9535(2) 0.0989(2) 0.7496(2) 0.0651(7) Uani 1 d . . O2A O 1.4394(31) 0.0031(33) 1.0754(14) 0.092(7) Uani 0.52(11) d PU 1 O2B O 1.4565(21) -0.0606(110) 1.0688(24) 0.129(17) Uani 0.48(11) d PU 2 O3 O 1.3554(3) -0.1135(4) 1.1354(2) 0.1257(15) Uani 1 d . . N1 N 0.9988(2) -0.1153(3) 0.7508(2) 0.0526(7) Uani 1 d . . H1 H 0.9851(2) -0.1944(3) 0.7234(2) 0.063 Uiso 1 d R . N2 N 1.3644(3) -0.0734(4) 1.0708(2) 0.0764(10) Uani 1 d . . N3 N 0.5523(3) -0.0675(4) 0.3976(2) 0.0861(11) Uani 1 d . . C1 C 1.0930(3) -0.1040(3) 0.8321(2) 0.0481(8) Uani 1 d . . C2 C 1.0818(3) -0.1536(3) 0.9073(2) 0.0507(9) Uani 1 d . . C3 C 1.1733(3) -0.1429(3) 0.9857(2) 0.0558(9) Uani 1 d . . H3A H 1.1706(3) -0.1777(3) 1.0384(2) 0.067 Uiso 1 d R . C4 C 1.2690(3) -0.0848(3) 0.9867(2) 0.0559(9) Uani 1 d . . C5 C 1.2807(3) -0.0380(3) 0.9129(2) 0.0568(9) Uani 1 d . . H5A H 1.3494(3) 0.0009(3) 0.9164(2) 0.068 Uiso 1 d R . C6 C 1.1911(3) -0.0481(3) 0.8334(2) 0.0512(9) Uani 1 d . . C7 C 0.9313(3) -0.0114(4) 0.7153(2) 0.0510(9) Uani 1 d . . C8 C 0.8311(3) -0.0339(3) 0.6343(2) 0.0494(9) Uani 1 d . . C9 C 0.8018(3) -0.1550(4) 0.5918(2) 0.0608(10) Uani 1 d . . H9A H 0.8469(3) -0.2319(4) 0.6155(2) 0.073 Uiso 1 d R . C10 C 0.7083(3) -0.1676(4) 0.5144(2) 0.0674(11) Uani 1 d . . H10A H 0.6881(3) -0.2529(4) 0.4869(2) 0.081 Uiso 1 d R . C11 C 0.6423(3) -0.0579(4) 0.4766(2) 0.0641(11) Uani 1 d . . C12 C 0.6704(3) 0.0625(4) 0.5206(2) 0.0666(11) Uani 1 d . . H12A H 0.6254(3) 0.1397(4) 0.4971(2) 0.080 Uiso 1 d R . C13 C 0.7614(3) 0.0721(4) 0.5980(2) 0.0609(10) Uani 1 d . . H13A H 0.7771(3) 0.1558(4) 0.6281(2) 0.073 Uiso 1 d R . C14 C 0.9738(3) -0.2178(4) 0.9020(2) 0.0615(10) Uani 1 d . . H14A H 0.9401(3) -0.2577(4) 0.8454(2) 0.074 Uiso 1 d R . C15 C 0.9915(4) -0.3262(5) 0.9700(3) 0.0898(14) Uani 1 d . . H15C H 0.9207(4) -0.3632(5) 0.9628(3) 0.135 Uiso 1 d R . H15B H 1.0383(4) -0.3950(5) 0.9629(3) 0.135 Uiso 1 d R . H15A H 1.0259(4) -0.2884(5) 1.0271(3) 0.135 Uiso 1 d R . C16 C 0.8918(3) -0.1149(4) 0.9082(3) 0.0871(14) Uani 1 d . . H16C H 0.8805(3) -0.0460(4) 0.8657(3) 0.131 Uiso 1 d R . H16B H 0.8220(3) -0.1566(4) 0.8989(3) 0.131 Uiso 1 d R . H16A H 0.9222(3) -0.0770(4) 0.9655(3) 0.131 Uiso 1 d R . C17 C 1.2025(3) -0.0077(4) 0.7487(2) 0.0595(10) Uani 1 d . . H17A H 1.1308(3) 0.0222(4) 0.7092(2) 0.071 Uiso 1 d R . C18 C 1.2833(4) 0.1055(5) 0.7591(3) 0.0896(14) Uani 1 d . . H18C H 1.2865(4) 0.1283(5) 0.7042(3) 0.134 Uiso 1 d R . H18B H 1.2609(4) 0.1819(5) 0.7828(3) 0.134 Uiso 1 d R . H18A H 1.3553(4) 0.0766(5) 0.7986(3) 0.134 Uiso 1 d R . C19 C 1.2331(4) -0.1285(5) 0.7077(3) 0.097(2) Uani 1 d . . H19C H 1.1802(4) -0.1988(5) 0.6994(3) 0.145 Uiso 1 d R . H19B H 1.2349(4) -0.1042(5) 0.6526(3) 0.145 Uiso 1 d R . H19A H 1.3054(4) -0.1581(5) 0.7461(3) 0.145 Uiso 1 d R . C20 C 0.5148(4) -0.1959(5) 0.3575(3) 0.109(2) Uani 1 d . . H20C H 0.5622(4) -0.2650(5) 0.3922(3) 0.163 Uiso 1 d R . H20B H 0.4402(4) -0.2104(5) 0.3533(3) 0.163 Uiso 1 d R . H20A H 0.5160(4) -0.1971(5) 0.3004(3) 0.163 Uiso 1 d R . C21 C 0.4891(4) 0.0485(5) 0.3545(3) 0.100(2) Uani 1 d . . H21C H 0.5211(4) 0.1281(5) 0.3859(3) 0.150 Uiso 1 d R . H21B H 0.4897(4) 0.0531(5) 0.2972(3) 0.150 Uiso 1 d R . H21A H 0.4139(4) 0.0399(5) 0.3501(3) 0.150 Uiso 1 d 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 O1 0.067(2) 0.0444(14) 0.067(2) -0.0019(12) 0.0081(13) -0.0002(13) O2A 0.072(9) 0.105(14) 0.074(5) 0.001(7) 0.002(5) -0.029(7) O2B 0.059(7) 0.219(44) 0.083(9) 0.041(17) -0.001(5) -0.015(14) O3 0.118(3) 0.189(4) 0.047(2) 0.016(2) 0.007(2) -0.031(3) N1 0.057(2) 0.044(2) 0.047(2) -0.0019(13) 0.0092(13) 0.0001(14) N2 0.071(2) 0.086(3) 0.056(2) 0.006(2) 0.007(2) -0.003(2) N3 0.074(2) 0.102(3) 0.058(2) 0.002(2) -0.001(2) -0.019(2) C1 0.053(2) 0.042(2) 0.044(2) -0.002(2) 0.014(2) 0.002(2) C2 0.057(2) 0.046(2) 0.048(2) -0.007(2) 0.018(2) 0.000(2) C3 0.068(2) 0.053(2) 0.046(2) -0.002(2) 0.022(2) 0.000(2) C4 0.056(2) 0.054(2) 0.047(2) 0.003(2) 0.009(2) 0.004(2) C5 0.054(2) 0.054(2) 0.058(2) 0.006(2) 0.017(2) 0.002(2) C6 0.050(2) 0.050(2) 0.048(2) 0.006(2) 0.013(2) 0.004(2) C7 0.055(2) 0.046(2) 0.050(2) 0.004(2) 0.019(2) -0.002(2) C8 0.050(2) 0.050(2) 0.047(2) 0.004(2) 0.018(2) -0.002(2) C9 0.060(2) 0.063(2) 0.056(2) 0.002(2) 0.018(2) 0.002(2) C10 0.069(3) 0.070(3) 0.055(2) -0.011(2) 0.014(2) -0.008(2) C11 0.052(2) 0.086(3) 0.047(2) 0.007(2) 0.012(2) -0.015(2) C12 0.058(2) 0.066(3) 0.062(2) 0.010(2) 0.008(2) -0.003(2) C13 0.057(2) 0.054(2) 0.061(2) 0.004(2) 0.012(2) -0.006(2) C14 0.068(2) 0.059(2) 0.059(2) -0.007(2) 0.027(2) -0.012(2) C15 0.095(3) 0.087(3) 0.100(3) 0.018(3) 0.051(3) -0.008(3) C16 0.070(3) 0.082(3) 0.116(4) -0.015(3) 0.043(3) -0.001(2) C17 0.054(2) 0.069(3) 0.053(2) 0.012(2) 0.018(2) 0.010(2) C18 0.078(3) 0.117(4) 0.078(3) 0.023(3) 0.036(2) -0.011(3) C19 0.124(4) 0.104(4) 0.070(3) 0.009(3) 0.046(3) 0.027(3) C20 0.100(4) 0.129(4) 0.067(3) -0.011(3) -0.001(3) -0.037(4) C21 0.074(3) 0.129(4) 0.068(3) 0.025(3) -0.004(2) -0.010(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 O1 C7 1.230(4) . ? O2A N2 1.22(2) . ? O2B N2 1.22(3) . ? O3 N2 1.199(4) . ? N1 C7 1.347(4) . ? N1 C1 1.438(4) . ? N2 C4 1.474(5) . ? N3 C11 1.387(5) . ? N3 C21 1.449(6) . ? N3 C20 1.450(6) . ? C1 C6 1.393(5) . ? C1 C2 1.409(5) . ? C2 C3 1.390(5) . ? C2 C14 1.522(5) . ? C3 C4 1.373(5) . ? C4 C5 1.380(5) . ? C5 C6 1.390(4) . ? C6 C17 1.532(5) . ? C7 C8 1.488(4) . ? C8 C13 1.380(5) . ? C8 C9 1.386(5) . ? C9 C10 1.397(5) . ? C10 C11 1.391(5) . ? C11 C12 1.390(5) . ? C12 C13 1.377(5) . ? C14 C16 1.522(5) . ? C14 C15 1.525(5) . ? C17 C18 1.516(5) . ? C17 C19 1.520(6) . ? 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 C7 N1 C1 121.8(3) . . ? O3 N2 O2B 120.1(12) . . ? O3 N2 O2A 120.7(11) . . ? O3 N2 C4 119.1(4) . . ? O2B N2 C4 117.4(19) . . ? O2A N2 C4 118.0(13) . . ? C11 N3 C21 121.7(4) . . ? C11 N3 C20 120.6(4) . . ? C21 N3 C20 117.6(3) . . ? C6 C1 C2 122.9(3) . . ? C6 C1 N1 119.4(3) . . ? C2 C1 N1 117.7(3) . . ? C3 C2 C1 117.4(3) . . ? C3 C2 C14 121.8(3) . . ? C1 C2 C14 120.8(3) . . ? C4 C3 C2 119.4(3) . . ? C3 C4 C5 123.3(3) . . ? C3 C4 N2 118.3(3) . . ? C5 C4 N2 118.4(3) . . ? C4 C5 C6 118.8(3) . . ? C5 C6 C1 118.2(3) . . ? C5 C6 C17 120.9(3) . . ? C1 C6 C17 120.8(3) . . ? O1 C7 N1 120.0(3) . . ? O1 C7 C8 121.6(3) . . ? N1 C7 C8 118.4(3) . . ? C13 C8 C9 116.8(3) . . ? C13 C8 C7 118.6(3) . . ? C9 C8 C7 124.6(3) . . ? C8 C9 C10 121.4(4) . . ? C11 C10 C9 120.8(4) . . ? N3 C11 C12 120.9(4) . . ? N3 C11 C10 121.5(4) . . ? C12 C11 C10 117.6(3) . . ? C13 C12 C11 120.7(4) . . ? C12 C13 C8 122.6(4) . . ? C2 C14 C16 111.6(3) . . ? C2 C14 C15 113.0(3) . . ? C16 C14 C15 110.1(3) . . ? C18 C17 C19 111.0(4) . . ? C18 C17 C6 113.9(3) . . ? C19 C17 C6 109.8(3) . . ? 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 C7 N1 C1 C6 -80.4(4) . . . . ? C7 N1 C1 C2 101.0(4) . . . . ? C6 C1 C2 C3 1.2(5) . . . . ? N1 C1 C2 C3 179.7(3) . . . . ? C6 C1 C2 C14 -178.0(3) . . . . ? N1 C1 C2 C14 0.5(5) . . . . ? C1 C2 C3 C4 0.4(5) . . . . ? C14 C2 C3 C4 179.6(3) . . . . ? C2 C3 C4 C5 -1.5(5) . . . . ? C2 C3 C4 N2 179.4(3) . . . . ? O3 N2 C4 C3 -0.9(6) . . . . ? O2B N2 C4 C3 158.2(59) . . . . ? O2A N2 C4 C3 -164.0(23) . . . . ? O3 N2 C4 C5 179.9(4) . . . . ? O2B N2 C4 C5 -21.0(59) . . . . ? O2A N2 C4 C5 16.8(24) . . . . ? C3 C4 C5 C6 1.0(5) . . . . ? N2 C4 C5 C6 -179.9(3) . . . . ? C4 C5 C6 C1 0.6(5) . . . . ? C4 C5 C6 C17 -175.2(3) . . . . ? C2 C1 C6 C5 -1.7(5) . . . . ? N1 C1 C6 C5 179.9(3) . . . . ? C2 C1 C6 C17 174.1(3) . . . . ? N1 C1 C6 C17 -4.3(5) . . . . ? C1 N1 C7 O1 4.9(5) . . . . ? C1 N1 C7 C8 -175.7(3) . . . . ? O1 C7 C8 C13 -0.9(5) . . . . ? N1 C7 C8 C13 179.7(3) . . . . ? O1 C7 C8 C9 179.2(3) . . . . ? N1 C7 C8 C9 -0.2(5) . . . . ? C13 C8 C9 C10 2.1(5) . . . . ? C7 C8 C9 C10 -177.9(3) . . . . ? C8 C9 C10 C11 1.0(6) . . . . ? C21 N3 C11 C12 4.7(6) . . . . ? C20 N3 C11 C12 -172.1(4) . . . . ? C21 N3 C11 C10 -174.7(4) . . . . ? C20 N3 C11 C10 8.6(6) . . . . ? C9 C10 C11 N3 176.8(4) . . . . ? C9 C10 C11 C12 -2.5(6) . . . . ? N3 C11 C12 C13 -178.4(4) . . . . ? C10 C11 C12 C13 0.9(6) . . . . ? C11 C12 C13 C8 2.3(6) . . . . ? C9 C8 C13 C12 -3.8(5) . . . . ? C7 C8 C13 C12 176.3(3) . . . . ? C3 C2 C14 C16 94.4(4) . . . . ? C1 C2 C14 C16 -86.4(4) . . . . ? C3 C2 C14 C15 -30.2(5) . . . . ? C1 C2 C14 C15 148.9(3) . . . . ? C5 C6 C17 C18 -32.3(5) . . . . ? C1 C6 C17 C18 152.0(3) . . . . ? C5 C6 C17 C19 92.9(4) . . . . ? C1 C6 C17 C19 -82.7(4) . . . . ? _refine_diff_density_max 0.231 _refine_diff_density_min -0.189 _refine_diff_density_rms 0.045