# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2002 data_global _journal_coden_Cambridge 188 _publ_requested_journal 'Perkin Transactions 2' loop_ _publ_author_name 'Geise, Herman J.' 'Blockhuys, Frank' 'Lenstra, Albert T. H.' 'Van Alsenoy, Christian' 'Vande Velde, Christophe M. L.' _publ_contact_author_name 'Prof Herman J. Geise' _publ_contact_author_address ; Chemistry U.I.A. , Antwerp University Universiteitsplein 1 Antwerpen B-2610 BELGIUM ; _publ_contact_author_email 'GEISE@UIA.UA.AC.BE' _publ_contact_author_fax '3238202310' _publ_contact_author_phone '3238202349' _publ_section_title ; SUBSTITUENT EFFECTS FAVOURING THE CIS-CONFIGURATION IN METHOXY AND CYANO SUBSTITUTED STILBENE DERIVATIVES ; _publ_contact_letter ; Please consider this CIF as supplementary material for the publication in J. Chem. Soc. Perkin Trans 2 ; data_cbmpe _database_code_CSD 179551 _audit_creation_method SHELXL-97 _chemical_name_systematic ; (Z)-1-cyano-1,2-bis(2-methoxyphenyl)ethene ; _chemical_name_common ? _chemical_melting_point '104-106C' _chemical_formula_moiety C17H15NO2 _chemical_formula_sum 'C17 H15 N O2' _chemical_formula_weight 265.30 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 'P b c a ' 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' '-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 7.2179(15) _cell_length_b 14.926(3) _cell_length_c 26.015(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2802.7(9) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 13 _cell_measurement_theta_max 17 _exptl_crystal_description needle _exptl_crystal_colour 'light yellow' _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.257 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1120 _exptl_absorpt_coefficient_mu 0.083 _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 Enraf_Nonius_CAD4 _diffrn_measurement_method \w/2\q _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 120 _diffrn_standards_decay_% 0.00 _diffrn_reflns_number 16292 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0173 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 36 _diffrn_reflns_theta_min 1.57 _diffrn_reflns_theta_max 29.96 _reflns_number_total 4073 _reflns_number_gt 2760 _reflns_threshold_expression >2sigma(I) _computing_data_collection CAD4_(Enraf-Nonius,_1977) _computing_cell_refinement CAD4_(Enraf-Nonius,_1977) _computing_data_reduction process_MolEN_(Fair,_1990) _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics PLATON (A.L. Spek, 2001) _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^)+(0.0154P)^2^+3.3712P] 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 4073 _refine_ls_number_parameters 241 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1222 _refine_ls_R_factor_gt 0.0764 _refine_ls_wR_factor_ref 0.1527 _refine_ls_wR_factor_gt 0.1233 _refine_ls_goodness_of_fit_ref 1.164 _refine_ls_restrained_S_all 1.164 _refine_ls_shift/su_max 0.016 _refine_ls_shift/su_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_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 C7 C 0.1810(3) 0.14048(16) 0.37705(8) 0.0381(5) Uani 1 1 d . . . O9B O 0.4070(3) 0.26182(12) 0.32623(7) 0.0558(5) Uani 1 1 d . . . C1A C -0.0236(3) 0.12184(16) 0.45479(9) 0.0393(5) Uani 1 1 d . . . C8 C 0.1387(3) 0.10374(17) 0.42311(9) 0.0390(5) Uani 1 1 d . . . C1B C 0.3446(3) 0.11213(16) 0.34636(8) 0.0378(5) Uani 1 1 d . . . C2A C -0.0029(4) 0.12344(17) 0.50853(9) 0.0445(6) Uani 1 1 d . . . O9A O 0.1725(3) 0.10765(14) 0.52547(7) 0.0561(5) Uani 1 1 d . . . C2B C 0.4538(4) 0.17409(17) 0.31963(9) 0.0420(5) Uani 1 1 d . . . C6B C 0.3925(4) 0.02198(18) 0.34325(10) 0.0463(6) Uani 1 1 d . . . N12 N -0.0263(4) 0.26410(18) 0.33851(10) 0.0664(7) Uani 1 1 d . . . C6A C -0.2004(4) 0.13547(19) 0.43452(11) 0.0488(6) Uani 1 1 d . . . C3A C -0.1526(5) 0.1428(2) 0.54002(11) 0.0552(7) Uani 1 1 d . . . C3B C 0.6019(4) 0.1452(2) 0.28995(10) 0.0515(7) Uani 1 1 d . . . C4B C 0.6444(4) 0.0549(2) 0.28752(10) 0.0571(8) Uani 1 1 d . . . C11 C 0.0656(4) 0.20979(18) 0.35605(9) 0.0453(6) Uani 1 1 d . . . C4A C -0.3240(4) 0.1572(2) 0.51831(13) 0.0633(8) Uani 1 1 d . . . C10A C 0.2009(6) 0.1048(3) 0.57965(12) 0.0688(10) Uani 1 1 d . . . C5A C -0.3502(4) 0.1528(2) 0.46599(13) 0.0608(8) Uani 1 1 d . . . C5B C 0.5429(4) -0.0065(2) 0.31463(11) 0.0550(7) Uani 1 1 d . . . C10B C 0.4952(6) 0.3272(2) 0.29497(13) 0.0628(8) Uani 1 1 d . . . 10A1 H 0.179(5) 0.167(3) 0.5953(13) 0.094(13) Uiso 1 1 d . . . 10A2 H 0.329(5) 0.081(2) 0.5837(12) 0.079(11) Uiso 1 1 d . . . H5B H 0.569(4) -0.069(2) 0.3137(11) 0.067(9) Uiso 1 1 d . . . 10B1 H 0.633(6) 0.327(2) 0.3035(13) 0.098(13) Uiso 1 1 d . . . H3B H 0.674(4) 0.189(2) 0.2725(11) 0.066(9) Uiso 1 1 d . . . H8 H 0.233(4) 0.0619(17) 0.4368(9) 0.046(7) Uiso 1 1 d . . . H6B H 0.319(4) -0.0196(17) 0.3616(10) 0.048(7) Uiso 1 1 d . . . 10B2 H 0.481(5) 0.311(2) 0.2593(13) 0.078(10) Uiso 1 1 d . . . H6A H -0.218(4) 0.1302(19) 0.3974(11) 0.065(9) Uiso 1 1 d . . . 10B3 H 0.436(4) 0.387(2) 0.3028(12) 0.073(10) Uiso 1 1 d . . . H5A H -0.477(5) 0.160(2) 0.4517(13) 0.086(11) Uiso 1 1 d . . . H3A H -0.129(4) 0.147(2) 0.5770(12) 0.067(9) Uiso 1 1 d . . . 10A3 H 0.119(5) 0.059(2) 0.5957(12) 0.079(11) Uiso 1 1 d . . . H4B H 0.749(5) 0.035(2) 0.2666(11) 0.077(10) Uiso 1 1 d . . . H4A H -0.427(4) 0.170(2) 0.5415(11) 0.067(9) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C7 0.0385(12) 0.0419(12) 0.0338(10) 0.0000(9) -0.0015(9) 0.0001(10) O9B 0.0610(12) 0.0444(10) 0.0619(11) 0.0019(9) 0.0173(10) -0.0031(9) C1A 0.0403(12) 0.0394(12) 0.0382(11) 0.0021(10) 0.0006(10) 0.0002(10) C8 0.0384(12) 0.0416(12) 0.0370(11) 0.0004(10) -0.0021(10) -0.0001(11) C1B 0.0387(12) 0.0447(12) 0.0299(10) -0.0022(9) -0.0017(9) 0.0019(10) C2A 0.0466(14) 0.0439(13) 0.0429(13) 0.0023(10) 0.0019(11) -0.0053(11) O9A 0.0543(11) 0.0782(14) 0.0359(9) 0.0066(9) -0.0039(8) -0.0018(11) C2B 0.0426(13) 0.0465(13) 0.0370(11) -0.0011(10) -0.0013(10) 0.0013(11) C6B 0.0525(15) 0.0462(14) 0.0402(12) 0.0021(11) -0.0016(12) 0.0030(13) N12 0.0649(16) 0.0684(16) 0.0659(15) 0.0219(13) 0.0089(13) 0.0182(14) C6A 0.0415(14) 0.0541(15) 0.0509(15) 0.0029(13) -0.0004(12) -0.0021(12) C3A 0.0637(19) 0.0537(16) 0.0482(15) -0.0028(13) 0.0153(14) -0.0062(15) C3B 0.0471(15) 0.0637(18) 0.0436(13) 0.0005(13) 0.0074(12) 0.0011(14) C4B 0.0541(17) 0.075(2) 0.0420(13) -0.0032(14) 0.0076(13) 0.0185(16) C11 0.0458(14) 0.0512(14) 0.0390(12) 0.0028(11) 0.0069(11) 0.0023(12) C4A 0.0533(18) 0.0604(18) 0.076(2) -0.0011(16) 0.0266(17) -0.0020(15) C10A 0.080(3) 0.086(3) 0.0396(14) 0.0116(16) -0.0112(16) -0.016(2) C5A 0.0417(15) 0.0655(19) 0.075(2) 0.0048(16) 0.0073(15) 0.0003(15) C5B 0.0619(18) 0.0556(17) 0.0473(14) -0.0037(13) 0.0001(13) 0.0186(15) C10B 0.081(3) 0.0507(17) 0.0566(18) 0.0080(14) 0.0093(18) -0.0069(17) _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 C7 C8 1.353(3) . ? C7 C11 1.436(3) . ? C7 C1B 1.487(3) . ? O9B C2B 1.363(3) . ? O9B C10B 1.421(3) . ? C1A C6A 1.395(4) . ? C1A C2A 1.406(3) . ? C1A C8 1.458(3) . ? C8 H8 0.99(3) . ? C1B C6B 1.392(3) . ? C1B C2B 1.400(3) . ? C2A O9A 1.362(3) . ? C2A C3A 1.386(4) . ? O9A C10A 1.425(3) . ? C2B C3B 1.387(4) . ? C6B C5B 1.383(4) . ? C6B H6B 0.95(3) . ? N12 C11 1.142(3) . ? C6A C5A 1.381(4) . ? C6A H6A 0.98(3) . ? C3A C4A 1.377(4) . ? C3A H3A 0.98(3) . ? C3B C4B 1.383(4) . ? C3B H3B 0.96(3) . ? C4B C5B 1.370(4) . ? C4B H4B 0.98(3) . ? C4A C5A 1.376(5) . ? C4A H4A 0.97(3) . ? C10A 10A1 1.02(4) . ? C10A 10A2 1.00(4) . ? C10A 10A3 1.00(3) . ? C5A H5A 1.00(4) . ? C5B H5B 0.96(3) . ? C10B 10B1 1.02(4) . ? C10B 10B2 0.96(3) . ? C10B 10B3 1.01(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 C8 C7 C11 119.9(2) . . ? C8 C7 C1B 122.7(2) . . ? C11 C7 C1B 117.5(2) . . ? C2B O9B C10B 118.5(2) . . ? C6A C1A C2A 118.1(2) . . ? C6A C1A C8 123.2(2) . . ? C2A C1A C8 118.7(2) . . ? C7 C8 C1A 127.4(2) . . ? C7 C8 H8 114.7(14) . . ? C1A C8 H8 117.8(14) . . ? C6B C1B C2B 118.0(2) . . ? C6B C1B C7 120.2(2) . . ? C2B C1B C7 121.7(2) . . ? O9A C2A C3A 124.7(2) . . ? O9A C2A C1A 114.7(2) . . ? C3A C2A C1A 120.6(3) . . ? C2A O9A C10A 117.3(2) . . ? O9B C2B C3B 124.0(2) . . ? O9B C2B C1B 115.6(2) . . ? C3B C2B C1B 120.3(2) . . ? C5B C6B C1B 121.6(3) . . ? C5B C6B H6B 120.7(16) . . ? C1B C6B H6B 117.7(16) . . ? C5A C6A C1A 121.3(3) . . ? C5A C6A H6A 119.9(18) . . ? C1A C6A H6A 118.8(18) . . ? C4A C3A C2A 119.4(3) . . ? C4A C3A H3A 123.1(19) . . ? C2A C3A H3A 117.5(19) . . ? C4B C3B C2B 120.0(3) . . ? C4B C3B H3B 121.9(18) . . ? C2B C3B H3B 118.1(18) . . ? C5B C4B C3B 120.7(3) . . ? C5B C4B H4B 119.5(19) . . ? C3B C4B H4B 119.8(19) . . ? N12 C11 C7 178.7(3) . . ? C5A C4A C3A 121.5(3) . . ? C5A C4A H4A 121.2(18) . . ? C3A C4A H4A 117.3(18) . . ? O9A C10A 10A1 110(2) . . ? O9A C10A 10A2 104(2) . . ? 10A1 C10A 10A2 115(3) . . ? O9A C10A 10A3 110.5(19) . . ? 10A1 C10A 10A3 112(3) . . ? 10A2 C10A 10A3 105(3) . . ? C4A C5A C6A 119.2(3) . . ? C4A C5A H5A 119(2) . . ? C6A C5A H5A 121(2) . . ? C4B C5B C6B 119.4(3) . . ? C4B C5B H5B 122.4(19) . . ? C6B C5B H5B 118.1(19) . . ? O9B C10B 10B1 108(2) . . ? O9B C10B 10B2 110(2) . . ? 10B1 C10B 10B2 108(3) . . ? O9B C10B 10B3 107.5(18) . . ? 10B1 C10B 10B3 112(3) . . ? 10B2 C10B 10B3 112(3) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 29.96 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.259 _refine_diff_density_min -0.285 _refine_diff_density_rms 0.054 data_cpmpe _database_code_CSD 179552 _audit_creation_method SHELXL-97 _chemical_name_systematic ; (Z)-1-cyano-2-(2-methoxyphenyl)-1-phenylethene ; _chemical_name_common ? _chemical_melting_point '45-47 C' _chemical_formula_moiety 'C16 H13 N O' _chemical_formula_sum 'C16 H13 N O' _chemical_formula_weight 235.27 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/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 10.415(3) _cell_length_b 11.437(2) _cell_length_c 11.705(3) _cell_angle_alpha 90.00 _cell_angle_beta 113.86(2) _cell_angle_gamma 90.00 _cell_volume 1275.1(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 13 _cell_measurement_theta_max 17 _exptl_crystal_description cube _exptl_crystal_colour 'light yellow' _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.226 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 496 _exptl_absorpt_coefficient_mu 0.077 _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 Enraf_Nonius_CAD4 _diffrn_measurement_method \w/2\q _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 120 _diffrn_standards_decay_% 1 _diffrn_reflns_number 2861 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0784 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.14 _diffrn_reflns_theta_max 29.95 _reflns_number_total 2861 _reflns_number_gt 1235 _reflns_threshold_expression >2sigma(I) _computing_data_collection CAD4_(Enraf-Nonius,_1977) _computing_cell_refinement CAD4_(Enraf-Nonius,_1977) _computing_data_reduction process_MolEN_(Fair,_1990) _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (A.L. Spek, 2001)' _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^)+(0.0825P)^2^+0.1202P] 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 2861 _refine_ls_number_parameters 215 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1847 _refine_ls_R_factor_gt 0.0611 _refine_ls_wR_factor_ref 0.1862 _refine_ls_wR_factor_gt 0.1364 _refine_ls_goodness_of_fit_ref 1.004 _refine_ls_restrained_S_all 1.004 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O9A O 0.9387(2) 0.23451(18) 1.0148(2) 0.0724(7) Uani 1 1 d . . . C1A C 0.8001(3) 0.0667(2) 0.9452(3) 0.0527(8) Uani 1 1 d . . . C6B C 0.6253(3) 0.1568(3) 1.2226(3) 0.0579(8) Uani 1 1 d . . . C11 C 0.6871(3) -0.1123(3) 1.0731(3) 0.0571(8) Uani 1 1 d . . . C7 C 0.7025(3) 0.0090(2) 1.1046(3) 0.0521(7) Uani 1 1 d . . . C8 C 0.7580(3) 0.0844(3) 1.0487(3) 0.0562(8) Uani 1 1 d . . . C1B C 0.6611(3) 0.0422(2) 1.2077(3) 0.0500(7) Uani 1 1 d . . . N12 N 0.6740(4) -0.2107(2) 1.0538(3) 0.0805(9) Uani 1 1 d . . . C6A C 0.7482(4) -0.0227(3) 0.8575(3) 0.0679(9) Uani 1 1 d . . . C2A C 0.8921(3) 0.1467(2) 0.9279(3) 0.0581(8) Uani 1 1 d . . . C3A C 0.9290(4) 0.1374(3) 0.8273(3) 0.0702(10) Uani 1 1 d . . . C5B C 0.5900(4) 0.1865(3) 1.3215(3) 0.0671(9) Uani 1 1 d . . . C2B C 0.6591(4) -0.0409(3) 1.2937(3) 0.0628(9) Uani 1 1 d . . . C3B C 0.6253(4) -0.0100(4) 1.3925(3) 0.0749(10) Uani 1 1 d . . . C4A C 0.8777(4) 0.0459(4) 0.7452(4) 0.0825(11) Uani 1 1 d . . . C4B C 0.5921(4) 0.1026(4) 1.4062(4) 0.0775(11) Uani 1 1 d . . . C5A C 0.7867(4) -0.0327(4) 0.7588(3) 0.0822(11) Uani 1 1 d . . . C10A C 1.0143(7) 0.3278(4) 0.9911(7) 0.1030(18) Uani 1 1 d . . . H8 H 0.779(3) 0.167(3) 1.090(2) 0.060(8) Uiso 1 1 d . . . H6B H 0.627(3) 0.214(3) 1.161(3) 0.071(9) Uiso 1 1 d . . . H3A H 0.997(4) 0.191(3) 0.826(3) 0.084(11) Uiso 1 1 d . . . H2B H 0.681(3) -0.121(3) 1.284(3) 0.071(10) Uiso 1 1 d . . . H5B H 0.564(4) 0.271(3) 1.328(3) 0.094(11) Uiso 1 1 d . . . H5A H 0.750(4) -0.095(3) 0.697(4) 0.100(12) Uiso 1 1 d . . . 10A1 H 1.041(4) 0.381(4) 1.068(4) 0.105(13) Uiso 1 1 d . . . H6A H 0.671(4) -0.076(3) 0.865(3) 0.110(13) Uiso 1 1 d . . . H3B H 0.634(4) -0.067(3) 1.455(4) 0.112(14) Uiso 1 1 d . . . 10A2 H 1.093(5) 0.298(4) 0.992(4) 0.122(17) Uiso 1 1 d . . . H4A H 0.905(3) 0.038(3) 0.677(3) 0.084(10) Uiso 1 1 d . . . 10A3 H 0.963(9) 0.359(6) 0.908(7) 0.25(4) Uiso 1 1 d . . . H4B H 0.571(4) 0.128(3) 1.476(3) 0.084(10) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O9A 0.0796(16) 0.0574(12) 0.0941(17) -0.0125(12) 0.0495(14) -0.0158(12) C1A 0.0592(19) 0.0478(16) 0.0514(18) 0.0039(13) 0.0227(16) 0.0021(15) C6B 0.063(2) 0.0511(17) 0.059(2) -0.0031(16) 0.0241(17) -0.0075(16) C11 0.067(2) 0.0523(18) 0.0576(18) 0.0065(15) 0.0305(17) 0.0037(16) C7 0.0564(18) 0.0440(15) 0.0548(18) 0.0003(13) 0.0215(15) -0.0025(14) C8 0.065(2) 0.0514(17) 0.0524(19) 0.0004(14) 0.0238(17) -0.0006(15) C1B 0.0522(17) 0.0490(16) 0.0481(16) 0.0020(13) 0.0195(14) -0.0006(14) N12 0.115(3) 0.0520(16) 0.085(2) -0.0006(15) 0.051(2) -0.0010(17) C6A 0.079(2) 0.067(2) 0.059(2) -0.0053(17) 0.0287(19) -0.0098(19) C2A 0.059(2) 0.0523(17) 0.067(2) -0.0010(15) 0.0299(18) 0.0035(16) C3A 0.066(2) 0.074(2) 0.084(3) 0.001(2) 0.044(2) -0.0025(19) C5B 0.065(2) 0.067(2) 0.071(2) -0.0168(18) 0.0289(19) -0.0078(17) C2B 0.074(2) 0.0560(19) 0.059(2) 0.0089(16) 0.0275(18) 0.0028(18) C3B 0.091(3) 0.079(2) 0.058(2) 0.008(2) 0.034(2) -0.002(2) C4A 0.089(3) 0.100(3) 0.072(3) -0.007(2) 0.046(2) -0.003(2) C4B 0.090(3) 0.089(3) 0.064(2) -0.012(2) 0.042(2) -0.013(2) C5A 0.102(3) 0.086(3) 0.065(2) -0.017(2) 0.040(2) -0.015(2) C10A 0.108(4) 0.072(3) 0.165(6) -0.036(3) 0.092(4) -0.037(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 O9A C2A 1.372(3) . ? O9A C10A 1.418(5) . ? C1A C6A 1.393(4) . ? C1A C2A 1.398(4) . ? C1A C8 1.459(4) . ? C6B C5B 1.391(4) . ? C6B C1B 1.394(4) . ? C6B H6B 0.98(3) . ? C11 N12 1.144(3) . ? C11 C7 1.428(4) . ? C7 C8 1.347(4) . ? C7 C1B 1.485(4) . ? C8 H8 1.04(3) . ? C1B C2B 1.390(4) . ? C6A C5A 1.372(5) . ? C6A H6A 1.04(4) . ? C2A C3A 1.382(4) . ? C3A C4A 1.375(5) . ? C3A H3A 0.95(4) . ? C5B C4B 1.374(5) . ? C5B H5B 1.02(4) . ? C2B C3B 1.385(4) . ? C2B H2B 0.96(3) . ? C3B C4B 1.360(5) . ? C3B H3B 0.96(4) . ? C4A C5A 1.362(5) . ? C4A H4A 0.96(3) . ? C4B H4B 0.97(3) . ? C5A H5A 0.98(4) . ? C10A 10A1 1.03(4) . ? C10A 10A2 0.89(5) . ? C10A 10A3 0.96(7) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2A O9A C10A 117.6(3) . . ? C6A C1A C2A 117.2(3) . . ? C6A C1A C8 123.8(3) . . ? C2A C1A C8 118.9(3) . . ? C5B C6B C1B 120.5(3) . . ? C5B C6B H6B 122.4(17) . . ? C1B C6B H6B 117.0(17) . . ? N12 C11 C7 176.3(3) . . ? C8 C7 C11 121.5(3) . . ? C8 C7 C1B 123.6(3) . . ? C11 C7 C1B 114.8(2) . . ? C7 C8 C1A 130.3(3) . . ? C7 C8 H8 113.8(14) . . ? C1A C8 H8 115.8(15) . . ? C2B C1B C6B 118.0(3) . . ? C2B C1B C7 120.5(3) . . ? C6B C1B C7 121.5(2) . . ? C5A C6A C1A 121.6(3) . . ? C5A C6A H6A 122(2) . . ? C1A C6A H6A 116(2) . . ? O9A C2A C3A 123.5(3) . . ? O9A C2A C1A 115.4(3) . . ? C3A C2A C1A 121.1(3) . . ? C4A C3A C2A 119.4(3) . . ? C4A C3A H3A 124(2) . . ? C2A C3A H3A 116(2) . . ? C4B C5B C6B 119.9(3) . . ? C4B C5B H5B 122.4(19) . . ? C6B C5B H5B 117.7(19) . . ? C3B C2B C1B 120.9(3) . . ? C3B C2B H2B 119.5(18) . . ? C1B C2B H2B 119.6(18) . . ? C4B C3B C2B 120.2(3) . . ? C4B C3B H3B 121(2) . . ? C2B C3B H3B 119(2) . . ? C5A C4A C3A 120.9(4) . . ? C5A C4A H4A 119(2) . . ? C3A C4A H4A 120(2) . . ? C3B C4B C5B 120.5(4) . . ? C3B C4B H4B 123(2) . . ? C5B C4B H4B 117(2) . . ? C4A C5A C6A 119.8(4) . . ? C4A C5A H5A 118(2) . . ? C6A C5A H5A 122(2) . . ? O9A C10A 10A1 105(2) . . ? O9A C10A 10A2 107(3) . . ? 10A1 C10A 10A2 107(4) . . ? O9A C10A 10A3 110(5) . . ? 10A1 C10A 10A3 120(5) . . ? 10A2 C10A 10A3 107(5) . . ? _diffrn_measured_fraction_theta_max 0.773 _diffrn_reflns_theta_full 29.95 _diffrn_measured_fraction_theta_full 0.773 _refine_diff_density_max 0.182 _refine_diff_density_min -0.197 _refine_diff_density_rms 0.045