# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_imai813_1 #TrackingRef 'IMAI813-1Ver2.CIF' #data_im7584a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H19 N O2' _chemical_formula_weight 329.38 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 16.8936(16) _cell_length_b 7.6150(7) _cell_length_c 12.9428(12) _cell_angle_alpha 90.00 _cell_angle_beta 91.339(2) _cell_angle_gamma 90.00 _cell_volume 1664.6(3) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 2876 _cell_measurement_theta_min 1.21 _cell_measurement_theta_max 27.87 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.314 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 696 _exptl_absorpt_coefficient_mu 0.084 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9672 _exptl_absorpt_correction_T_max 0.9958 _exptl_absorpt_process_details 'Bruker SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(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 '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9908 _diffrn_reflns_av_R_equivalents 0.0388 _diffrn_reflns_av_sigmaI/netI 0.0557 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.21 _diffrn_reflns_theta_max 27.87 _reflns_number_total 3820 _reflns_number_gt 2876 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _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^)+(0.0815P)^2^+0.0862P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3820 _refine_ls_number_parameters 227 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0793 _refine_ls_R_factor_gt 0.0555 _refine_ls_wR_factor_ref 0.1516 _refine_ls_wR_factor_gt 0.1336 _refine_ls_goodness_of_fit_ref 1.062 _refine_ls_restrained_S_all 1.062 _refine_ls_shift/su_max 0.002 _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 C1 C 0.31648(11) 0.2794(2) 0.07490(13) 0.0171(4) Uani 1 1 d . . . H1 H 0.3220 0.2138 0.1371 0.020 Uiso 1 1 calc R . . C2 C 0.38253(10) 0.3288(2) 0.02384(13) 0.0157(4) Uani 1 1 d . . . C3 C 0.37539(11) 0.4318(2) -0.06720(14) 0.0180(4) Uani 1 1 d . . . H3 H 0.4215 0.4670 -0.1023 0.022 Uiso 1 1 calc R . . C4 C 0.30224(11) 0.4807(2) -0.10460(14) 0.0196(4) Uani 1 1 d . . . H4 H 0.2981 0.5520 -0.1647 0.023 Uiso 1 1 calc R . . C5 C 0.15621(11) 0.4702(3) -0.09356(15) 0.0232(4) Uani 1 1 d . . . H5 H 0.1506 0.5397 -0.1542 0.028 Uiso 1 1 calc R . . C6 C 0.09047(11) 0.4139(3) -0.04485(15) 0.0247(4) Uani 1 1 d . . . H6 H 0.0395 0.4437 -0.0720 0.030 Uiso 1 1 calc R . . C7 C 0.09732(11) 0.3115(3) 0.04571(15) 0.0246(4) Uani 1 1 d . . . H7 H 0.0510 0.2725 0.0790 0.030 Uiso 1 1 calc R . . C8 C 0.17005(11) 0.2682(3) 0.08584(14) 0.0212(4) Uani 1 1 d . . . H8 H 0.1741 0.2000 0.1472 0.025 Uiso 1 1 calc R . . C9 C 0.23958(10) 0.3241(2) 0.03670(13) 0.0169(4) Uani 1 1 d . . . C10 C 0.23286(11) 0.4267(2) -0.05513(14) 0.0181(4) Uani 1 1 d . . . C11 C 0.46250(10) 0.2633(2) 0.05971(13) 0.0161(4) Uani 1 1 d . . . O12 O 0.47693(7) 0.25706(17) 0.15652(9) 0.0202(3) Uani 1 1 d . . . O13 O 0.50935(7) 0.21453(17) -0.00772(9) 0.0197(3) Uani 1 1 d . . . C21 C 0.30893(10) 0.5953(2) 0.25716(13) 0.0148(4) Uani 1 1 d . . . C22 C 0.35118(11) 0.6818(2) 0.18425(13) 0.0168(4) Uani 1 1 d . . . H22 H 0.4072 0.6699 0.1844 0.020 Uiso 1 1 calc R . . C23 C 0.31375(11) 0.7878(3) 0.10908(14) 0.0218(4) Uani 1 1 d . . . H23 H 0.3446 0.8476 0.0597 0.026 Uiso 1 1 calc R . . C24 C 0.23378(11) 0.8057(3) 0.10631(14) 0.0223(4) Uani 1 1 d . . . H24 H 0.2091 0.8767 0.0545 0.027 Uiso 1 1 calc R . . C25 C 0.10338(11) 0.7364(3) 0.17919(14) 0.0239(4) Uani 1 1 d . . . H25 H 0.0779 0.8067 0.1277 0.029 Uiso 1 1 calc R . . C26 C 0.05878(11) 0.6535(3) 0.25094(15) 0.0270(5) Uani 1 1 d . . . H26 H 0.0028 0.6666 0.2495 0.032 Uiso 1 1 calc R . . C27 C 0.09606(11) 0.5486(3) 0.32709(15) 0.0250(5) Uani 1 1 d . . . H27 H 0.0649 0.4919 0.3773 0.030 Uiso 1 1 calc R . . C28 C 0.17613(11) 0.5271(2) 0.33004(14) 0.0196(4) Uani 1 1 d . . . H28 H 0.1998 0.4540 0.3815 0.024 Uiso 1 1 calc R . . C29 C 0.22477(10) 0.6125(2) 0.25721(13) 0.0160(4) Uani 1 1 d . . . C30 C 0.18679(11) 0.7196(2) 0.17991(14) 0.0189(4) Uani 1 1 d . . . C31 C 0.34809(10) 0.4815(2) 0.33851(13) 0.0170(4) Uani 1 1 d . . . H31A H 0.3397 0.5349 0.4071 0.020 Uiso 1 1 calc R . . H31B H 0.3221 0.3650 0.3378 0.020 Uiso 1 1 calc R . . N32 N 0.43405(8) 0.4569(2) 0.32476(11) 0.0155(3) Uani 1 1 d . . . H32A H 0.4422 0.4003 0.2640 0.023 Uiso 1 1 calc R . . H32B H 0.4544 0.3918 0.3780 0.023 Uiso 1 1 calc R . . H32C H 0.4584 0.5635 0.3238 0.023 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 C1 0.0227(10) 0.0137(9) 0.0148(8) -0.0022(7) -0.0001(7) 0.0012(7) C2 0.0166(9) 0.0152(9) 0.0152(8) -0.0051(7) -0.0003(7) -0.0003(7) C3 0.0205(10) 0.0142(9) 0.0195(9) -0.0018(7) 0.0015(7) -0.0022(7) C4 0.0255(11) 0.0159(9) 0.0173(9) 0.0009(7) 0.0000(8) 0.0007(7) C5 0.0258(11) 0.0222(11) 0.0214(10) -0.0005(8) -0.0027(8) 0.0058(8) C6 0.0189(10) 0.0290(11) 0.0262(10) -0.0053(9) -0.0037(8) 0.0073(8) C7 0.0186(10) 0.0278(11) 0.0276(10) -0.0044(9) 0.0039(8) -0.0006(8) C8 0.0238(10) 0.0196(10) 0.0202(9) -0.0010(8) 0.0016(8) 0.0016(8) C9 0.0195(9) 0.0146(9) 0.0167(9) -0.0045(7) 0.0002(7) 0.0011(7) C10 0.0216(10) 0.0135(9) 0.0189(9) -0.0026(7) -0.0009(7) 0.0020(7) C11 0.0164(9) 0.0142(9) 0.0175(9) -0.0024(7) -0.0016(7) -0.0029(7) O12 0.0218(7) 0.0222(7) 0.0164(6) -0.0034(5) -0.0021(5) 0.0044(5) O13 0.0159(7) 0.0258(8) 0.0175(6) -0.0037(5) 0.0018(5) -0.0004(5) C21 0.0202(9) 0.0121(9) 0.0121(8) -0.0036(7) -0.0011(7) 0.0003(7) C22 0.0166(9) 0.0164(9) 0.0173(9) -0.0007(7) 0.0004(7) 0.0010(7) C23 0.0265(10) 0.0203(10) 0.0187(9) 0.0052(8) 0.0040(8) -0.0004(8) C24 0.0285(11) 0.0209(10) 0.0175(9) 0.0040(8) -0.0030(8) 0.0041(8) C25 0.0235(10) 0.0279(11) 0.0200(9) -0.0060(8) -0.0051(8) 0.0054(8) C26 0.0165(10) 0.0369(12) 0.0275(10) -0.0086(9) -0.0020(8) 0.0031(8) C27 0.0200(10) 0.0311(12) 0.0242(10) -0.0027(9) 0.0046(8) -0.0036(8) C28 0.0227(10) 0.0206(10) 0.0156(9) -0.0014(7) -0.0004(7) 0.0001(8) C29 0.0191(9) 0.0146(9) 0.0141(8) -0.0030(7) -0.0007(7) 0.0012(7) C30 0.0223(10) 0.0179(10) 0.0164(9) -0.0040(7) -0.0024(7) 0.0018(7) C31 0.0166(9) 0.0194(10) 0.0150(9) 0.0018(7) 0.0009(7) 0.0008(7) N32 0.0175(8) 0.0160(8) 0.0129(7) 0.0023(6) -0.0010(6) 0.0012(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 C1 C2 1.363(2) . ? C1 C9 1.421(2) . ? C2 C3 1.418(2) . ? C2 C11 1.503(2) . ? C3 C4 1.368(3) . ? C4 C10 1.410(3) . ? C5 C6 1.359(3) . ? C5 C10 1.416(3) . ? C6 C7 1.410(3) . ? C7 C8 1.363(3) . ? C8 C9 1.414(2) . ? C9 C10 1.425(2) . ? C11 O13 1.248(2) . ? C11 O12 1.272(2) . ? C21 C22 1.366(2) . ? C21 C29 1.428(2) . ? C21 C31 1.505(2) . ? C22 C23 1.403(2) . ? C23 C24 1.358(3) . ? C24 C30 1.415(3) . ? C25 C26 1.364(3) . ? C25 C30 1.415(3) . ? C26 C27 1.406(3) . ? C27 C28 1.362(3) . ? C28 C29 1.422(2) . ? C29 C30 1.431(2) . ? C31 N32 1.479(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 C2 C1 C9 121.15(17) . . ? C1 C2 C3 120.05(16) . . ? C1 C2 C11 119.91(16) . . ? C3 C2 C11 119.89(16) . . ? C4 C3 C2 120.20(17) . . ? C3 C4 C10 120.89(17) . . ? C6 C5 C10 120.91(18) . . ? C5 C6 C7 120.53(18) . . ? C8 C7 C6 120.41(18) . . ? C7 C8 C9 120.42(18) . . ? C8 C9 C1 122.24(17) . . ? C8 C9 C10 119.31(17) . . ? C1 C9 C10 118.44(16) . . ? C4 C10 C5 122.37(17) . . ? C4 C10 C9 119.21(16) . . ? C5 C10 C9 118.42(17) . . ? O13 C11 O12 124.58(16) . . ? O13 C11 C2 117.56(15) . . ? O12 C11 C2 117.83(15) . . ? C22 C21 C29 119.52(16) . . ? C22 C21 C31 122.20(16) . . ? C29 C21 C31 118.29(15) . . ? C21 C22 C23 121.48(17) . . ? C24 C23 C22 120.53(17) . . ? C23 C24 C30 120.62(17) . . ? C26 C25 C30 121.31(19) . . ? C25 C26 C27 119.63(18) . . ? C28 C27 C26 121.08(18) . . ? C27 C28 C29 121.02(18) . . ? C28 C29 C21 123.32(16) . . ? C28 C29 C30 117.86(17) . . ? C21 C29 C30 118.82(16) . . ? C25 C30 C24 121.86(17) . . ? C25 C30 C29 119.10(17) . . ? C24 C30 C29 119.04(17) . . ? N32 C31 C21 113.93(14) . . ? _diffrn_measured_fraction_theta_max 0.964 _diffrn_reflns_theta_full 27.87 _diffrn_measured_fraction_theta_full 0.964 _refine_diff_density_max 0.366 _refine_diff_density_min -0.283 _refine_diff_density_rms 0.073 _database_code_depnum_ccdc_archive 'CCDC 933760' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_imai813_2 #TrackingRef 'IMAI813-1Ver2.CIF' #data_im7580a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H21 N O2' _chemical_formula_weight 379.44 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0000 '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) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 12.589(2) _cell_length_b 5.9903(9) _cell_length_c 14.136(2) _cell_angle_alpha 90.00 _cell_angle_beta 115.801(2) _cell_angle_gamma 90.00 _cell_volume 959.7(3) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 1974 _cell_measurement_theta_min 1.60 _cell_measurement_theta_max 1974 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.313 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 400 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9559 _exptl_absorpt_correction_T_max 0.9959 _exptl_absorpt_process_details 'Bruker SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(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 '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8438 _diffrn_reflns_av_R_equivalents 0.0501 _diffrn_reflns_av_sigmaI/netI 0.0557 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.60 _diffrn_reflns_theta_max 27.89 _reflns_number_total 2419 _reflns_number_gt 1974 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _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^)+(0.0589P)^2^+0.0191P] 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 constr _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 2419 _refine_ls_number_parameters 263 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0707 _refine_ls_R_factor_gt 0.0536 _refine_ls_wR_factor_ref 0.1201 _refine_ls_wR_factor_gt 0.1115 _refine_ls_goodness_of_fit_ref 1.097 _refine_ls_restrained_S_all 1.097 _refine_ls_shift/su_max 0.017 _refine_ls_shift/su_mean 0.005 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 C1 C 0.5909(3) 0.5535(5) 0.2132(2) 0.0158(7) Uani 1 1 d . . . H1 H 0.5885 0.4086 0.2396 0.019 Uiso 1 1 calc R . . C2 C 0.6973(3) 0.6603(5) 0.2461(2) 0.0145(6) Uani 1 1 d . . . C3 C 0.7018(3) 0.8776(5) 0.2057(2) 0.0165(7) Uani 1 1 d . . . H3 H 0.7753 0.9530 0.2289 0.020 Uiso 1 1 calc R . . C4 C 0.6018(3) 0.9768(5) 0.1343(2) 0.0165(7) Uani 1 1 d . . . H4 H 0.6068 1.1192 0.1069 0.020 Uiso 1 1 calc R . . C5 C 0.1673(3) 0.9648(6) -0.0757(2) 0.0220(7) Uani 1 1 d . . . H5 H 0.1691 1.1045 -0.1068 0.026 Uiso 1 1 calc R . . C6 C 0.0626(3) 0.8620(6) -0.1014(3) 0.0261(8) Uani 1 1 d . . . H6 H -0.0082 0.9304 -0.1503 0.031 Uiso 1 1 calc R . . C7 C 0.0571(3) 0.6528(7) -0.0562(3) 0.0258(8) Uani 1 1 d . . . H7 H -0.0172 0.5838 -0.0743 0.031 Uiso 1 1 calc R . . C8 C 0.1572(3) 0.5515(6) 0.0124(2) 0.0217(7) Uani 1 1 d . . . H8 H 0.1523 0.4117 0.0420 0.026 Uiso 1 1 calc R . . C9 C 0.3744(3) 0.5489(5) 0.1109(2) 0.0174(7) Uani 1 1 d . . . H9 H 0.3711 0.4059 0.1385 0.021 Uiso 1 1 calc R . . C10 C 0.3845(3) 0.9703(6) 0.0280(2) 0.0175(7) Uani 1 1 d . . . H10 H 0.3880 1.1120 -0.0008 0.021 Uiso 1 1 calc R . . C11 C 0.4884(2) 0.8703(5) 0.0995(2) 0.0149(6) Uani 1 1 d . . . C12 C 0.4844(2) 0.6531(5) 0.1410(2) 0.0153(6) Uani 1 1 d . . . C13 C 0.2698(3) 0.6515(6) 0.0411(2) 0.0194(7) Uani 1 1 d . . . C14 C 0.2752(3) 0.8661(6) -0.0022(2) 0.0167(7) Uani 1 1 d . . . C15 C 0.8070(3) 0.5469(5) 0.3250(2) 0.0183(7) Uani 1 1 d . . . O16 O 0.80014(19) 0.3473(4) 0.34618(18) 0.0264(6) Uani 1 1 d . . . O17 O 0.90079(17) 0.6649(4) 0.36592(15) 0.0188(5) Uani 1 1 d . . . C21 C 1.1963(3) 0.2837(5) 0.4106(2) 0.0171(7) Uani 1 1 d . . . C22 C 1.0965(3) 0.1521(6) 0.3739(2) 0.0194(7) Uani 1 1 d . . . H22 H 1.0344 0.1878 0.3923 0.023 Uiso 1 1 calc R . . C23 C 1.0851(3) -0.0348(6) 0.3094(2) 0.0251(8) Uani 1 1 d . . . H23 H 1.0153 -0.1224 0.2844 0.030 Uiso 1 1 calc R . . C24 C 1.1733(3) -0.0905(6) 0.2829(3) 0.0232(7) Uani 1 1 d . . . H24 H 1.1652 -0.2183 0.2405 0.028 Uiso 1 1 calc R . . C25 C 1.3704(3) -0.0143(6) 0.2904(2) 0.0230(8) Uani 1 1 d . . . H25 H 1.3633 -0.1424 0.2485 0.028 Uiso 1 1 calc R . . C26 C 1.4695(3) 0.1143(6) 0.3233(2) 0.0225(8) Uani 1 1 d . . . H26 H 1.5311 0.0751 0.3047 0.027 Uiso 1 1 calc R . . C27 C 1.4801(3) 0.3058(6) 0.3848(2) 0.0215(7) Uani 1 1 d . . . H27 H 1.5482 0.3973 0.4060 0.026 Uiso 1 1 calc R . . C28 C 1.3937(3) 0.3613(6) 0.4143(2) 0.0201(7) Uani 1 1 d . . . H28 H 1.4033 0.4890 0.4571 0.024 Uiso 1 1 calc R . . C29 C 1.2891(3) 0.2302(5) 0.3816(2) 0.0177(7) Uani 1 1 d . . . C30 C 1.2775(3) 0.0405(6) 0.3180(2) 0.0178(7) Uani 1 1 d . . . C31 C 1.2142(3) 0.4802(6) 0.4831(2) 0.0196(7) Uani 1 1 d . . . H31A H 1.2878 0.4567 0.5480 0.024 Uiso 1 1 calc R . . H31B H 1.2247 0.6166 0.4485 0.024 Uiso 1 1 calc R . . N32 N 1.1157(2) 0.5178(4) 0.51258(19) 0.0166(6) Uani 1 1 d . . . H32A H 1.0477 0.5418 0.4536 0.025 Uiso 1 1 calc R . . H32B H 1.1320 0.6392 0.5554 0.025 Uiso 1 1 calc R . . H32C H 1.1072 0.3956 0.5469 0.025 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 C1 0.0232(17) 0.0102(15) 0.0164(15) 0.0019(13) 0.0109(13) 0.0009(13) C2 0.0167(15) 0.0141(15) 0.0128(14) -0.0007(13) 0.0065(12) 0.0008(13) C3 0.0175(16) 0.0144(16) 0.0199(16) -0.0017(14) 0.0101(13) -0.0030(13) C4 0.0196(16) 0.0140(16) 0.0187(15) -0.0016(13) 0.0110(13) -0.0025(13) C5 0.0226(17) 0.0246(18) 0.0207(16) -0.0008(15) 0.0111(14) 0.0051(15) C6 0.0160(16) 0.038(2) 0.0229(17) 0.0015(17) 0.0071(14) 0.0077(16) C7 0.0162(16) 0.034(2) 0.0275(18) -0.0065(17) 0.0095(14) -0.0028(16) C8 0.0179(16) 0.0227(18) 0.0242(17) -0.0051(15) 0.0088(14) -0.0065(14) C9 0.0218(16) 0.0142(16) 0.0191(15) 0.0023(13) 0.0118(14) 0.0011(13) C10 0.0200(15) 0.0161(16) 0.0177(15) 0.0025(13) 0.0094(13) 0.0030(13) C11 0.0171(15) 0.0136(16) 0.0163(15) -0.0019(13) 0.0094(13) 0.0006(13) C12 0.0175(16) 0.0137(16) 0.0171(15) -0.0038(13) 0.0099(13) -0.0011(13) C13 0.0188(16) 0.0222(17) 0.0198(16) -0.0037(15) 0.0107(13) 0.0008(14) C14 0.0187(16) 0.0184(16) 0.0145(15) -0.0031(14) 0.0085(13) 0.0030(14) C15 0.0199(16) 0.0183(17) 0.0171(15) 0.0012(14) 0.0085(13) 0.0027(14) O16 0.0248(12) 0.0162(12) 0.0296(13) 0.0061(11) 0.0038(10) 0.0006(10) O17 0.0128(11) 0.0196(12) 0.0211(11) 0.0015(10) 0.0045(9) -0.0008(10) C21 0.0155(15) 0.0174(17) 0.0163(16) -0.0008(13) 0.0047(13) -0.0003(13) C22 0.0195(16) 0.0202(17) 0.0206(16) 0.0009(15) 0.0108(13) 0.0021(15) C23 0.0249(18) 0.0236(19) 0.0265(18) -0.0063(15) 0.0109(15) -0.0082(15) C24 0.0314(19) 0.0157(17) 0.0217(17) -0.0035(13) 0.0108(15) -0.0038(14) C25 0.0261(18) 0.0255(19) 0.0181(16) 0.0010(15) 0.0105(14) 0.0021(16) C26 0.0185(16) 0.032(2) 0.0205(16) 0.0024(15) 0.0117(14) 0.0038(15) C27 0.0189(16) 0.0246(19) 0.0218(17) 0.0005(14) 0.0097(14) -0.0003(14) C28 0.0202(16) 0.0184(17) 0.0200(16) -0.0021(15) 0.0072(14) 0.0004(14) C29 0.0188(16) 0.0165(17) 0.0159(15) 0.0049(13) 0.0057(13) 0.0040(13) C30 0.0213(16) 0.0168(16) 0.0146(14) 0.0015(13) 0.0071(13) 0.0035(14) C31 0.0158(15) 0.0203(17) 0.0238(16) -0.0004(14) 0.0096(13) 0.0004(14) N32 0.0165(13) 0.0132(13) 0.0194(13) -0.0009(11) 0.0071(11) 0.0007(11) _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 C1 C2 1.370(4) . ? C1 C12 1.415(4) . ? C2 C3 1.433(4) . ? C2 C15 1.507(4) . ? C3 C4 1.361(4) . ? C4 C11 1.440(4) . ? C5 C6 1.353(4) . ? C5 C14 1.431(4) . ? C6 C7 1.422(5) . ? C7 C8 1.354(4) . ? C8 C13 1.426(4) . ? C9 C13 1.398(4) . ? C9 C12 1.405(4) . ? C10 C11 1.392(4) . ? C10 C14 1.398(4) . ? C11 C12 1.438(4) . ? C13 C14 1.438(5) . ? C15 O16 1.244(4) . ? C15 O17 1.279(4) . ? C21 C22 1.378(4) . ? C21 C29 1.434(4) . ? C21 C31 1.512(4) . ? C22 C23 1.411(5) . ? C23 C24 1.359(4) . ? C24 C30 1.420(4) . ? C25 C26 1.364(4) . ? C25 C30 1.422(4) . ? C26 C27 1.411(5) . ? C27 C28 1.363(4) . ? C28 C29 1.426(4) . ? C29 C30 1.416(4) . ? C31 N32 1.487(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 C2 C1 C12 121.8(3) . . ? C1 C2 C3 119.5(3) . . ? C1 C2 C15 119.1(3) . . ? C3 C2 C15 121.5(3) . . ? C4 C3 C2 120.5(3) . . ? C3 C4 C11 121.3(3) . . ? C6 C5 C14 120.9(3) . . ? C5 C6 C7 120.8(3) . . ? C8 C7 C6 120.3(3) . . ? C7 C8 C13 121.0(3) . . ? C13 C9 C12 121.4(3) . . ? C11 C10 C14 121.2(3) . . ? C10 C11 C12 119.8(3) . . ? C10 C11 C4 122.3(3) . . ? C12 C11 C4 117.8(3) . . ? C9 C12 C1 122.0(3) . . ? C9 C12 C11 118.8(3) . . ? C1 C12 C11 119.1(3) . . ? C9 C13 C8 122.1(3) . . ? C9 C13 C14 119.3(3) . . ? C8 C13 C14 118.7(3) . . ? C10 C14 C5 122.3(3) . . ? C10 C14 C13 119.5(3) . . ? C5 C14 C13 118.2(3) . . ? O16 C15 O17 124.7(3) . . ? O16 C15 C2 118.3(3) . . ? O17 C15 C2 117.0(3) . . ? C22 C21 C29 119.1(3) . . ? C22 C21 C31 122.9(3) . . ? C29 C21 C31 117.9(3) . . ? C21 C22 C23 121.1(3) . . ? C24 C23 C22 120.5(3) . . ? C23 C24 C30 120.6(3) . . ? C26 C25 C30 121.0(3) . . ? C25 C26 C27 119.7(3) . . ? C28 C27 C26 120.9(3) . . ? C27 C28 C29 120.9(3) . . ? C30 C29 C28 118.2(3) . . ? C30 C29 C21 119.3(3) . . ? C28 C29 C21 122.5(3) . . ? C29 C30 C24 119.3(3) . . ? C29 C30 C25 119.3(3) . . ? C24 C30 C25 121.4(3) . . ? N32 C31 C21 114.3(2) . . ? _diffrn_measured_fraction_theta_max 0.964 _diffrn_reflns_theta_full 27.89 _diffrn_measured_fraction_theta_full 0.964 _refine_diff_density_max 0.266 _refine_diff_density_min -0.246 _refine_diff_density_rms 0.051 _database_code_depnum_ccdc_archive 'CCDC 933761' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_imai813_3 #TrackingRef 'IMAI813-1Ver2.CIF' #data_im1618b _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H21 N O2' _chemical_formula_weight 403.46 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 18.302(6) _cell_length_b 8.680(3) _cell_length_c 12.923(4) _cell_angle_alpha 90.00 _cell_angle_beta 105.172(5) _cell_angle_gamma 90.00 _cell_volume 1981.5(11) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3688 _cell_measurement_theta_min 2.61 _cell_measurement_theta_max 31.07 _exptl_crystal_description Platelet _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.352 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 848 _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9767 _exptl_absorpt_correction_T_max 0.9958 _exptl_absorpt_process_details multi-scan _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku Saturn' _diffrn_measurement_method \w-scans _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14062 _diffrn_reflns_av_R_equivalents 0.0525 _diffrn_reflns_av_sigmaI/netI 0.0509 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.61 _diffrn_reflns_theta_max 31.07 _reflns_number_total 5255 _reflns_number_gt 3688 _reflns_threshold_expression >2\s(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0929P)^2^+0.3684P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5255 _refine_ls_number_parameters 281 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0826 _refine_ls_R_factor_gt 0.0585 _refine_ls_wR_factor_ref 0.1681 _refine_ls_wR_factor_gt 0.1502 _refine_ls_goodness_of_fit_ref 1.077 _refine_ls_restrained_S_all 1.077 _refine_ls_shift/su_max 0.009 _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 O1 O 0.51301(7) 0.18320(15) 0.50431(10) 0.0219(3) Uani 1 1 d . . . O2 O 0.47934(7) 0.24115(15) 0.33022(9) 0.0216(3) Uani 1 1 d . . . C1 C 0.40044(9) 0.32630(18) 0.44029(13) 0.0176(3) Uani 1 1 d . . . C2 C 0.41018(10) 0.4341(2) 0.52315(13) 0.0198(3) Uani 1 1 d . . . H2 H 0.4596 0.4530 0.5674 0.024 Uiso 1 1 calc R . . C3 C 0.34955(10) 0.5138(2) 0.54223(14) 0.0206(3) Uani 1 1 d . . . H3 H 0.3580 0.5897 0.5971 0.025 Uiso 1 1 calc R . . C4 C 0.27579(10) 0.48335(19) 0.48116(13) 0.0186(3) Uani 1 1 d . . . C5 C 0.21136(10) 0.5636(2) 0.49861(14) 0.0232(4) Uani 1 1 d . . . H5 H 0.2191 0.6439 0.5503 0.028 Uiso 1 1 calc R . . C6 C 0.14008(10) 0.5274(2) 0.44328(15) 0.0243(4) Uani 1 1 d . . . H6 H 0.0987 0.5807 0.4585 0.029 Uiso 1 1 calc R . . C7 C 0.12539(10) 0.4106(2) 0.36214(14) 0.0215(3) Uani 1 1 d . . . C8 C 0.05251(10) 0.3725(2) 0.30260(15) 0.0273(4) Uani 1 1 d . . . H8 H 0.0103 0.4224 0.3178 0.033 Uiso 1 1 calc R . . C9 C 0.04035(11) 0.2635(2) 0.22179(17) 0.0306(4) Uani 1 1 d . . . H9 H -0.0098 0.2398 0.1821 0.037 Uiso 1 1 calc R . . C10 C 0.10139(10) 0.1885(2) 0.19840(16) 0.0286(4) Uani 1 1 d . . . H10 H 0.0926 0.1139 0.1427 0.034 Uiso 1 1 calc R . . C11 C 0.17584(10) 0.2221(2) 0.25654(14) 0.0221(4) Uani 1 1 d . . . C12 C 0.23996(10) 0.1456(2) 0.23652(14) 0.0239(4) Uani 1 1 d . . . H12 H 0.2320 0.0692 0.1821 0.029 Uiso 1 1 calc R . . C13 C 0.31168(10) 0.1786(2) 0.29264(14) 0.0212(3) Uani 1 1 d . . . H13 H 0.3527 0.1258 0.2763 0.025 Uiso 1 1 calc R . . C14 C 0.32688(9) 0.29262(19) 0.37688(13) 0.0168(3) Uani 1 1 d . . . C15 C 0.26384(9) 0.36994(19) 0.39926(13) 0.0172(3) Uani 1 1 d . . . C16 C 0.18852(9) 0.33381(19) 0.33925(13) 0.0190(3) Uani 1 1 d . . . C17 C 0.46936(9) 0.24460(19) 0.42378(13) 0.0177(3) Uani 1 1 d . . . C21 C 0.32892(9) 0.55853(19) 0.17159(13) 0.0179(3) Uani 1 1 d . . . C22 C 0.36638(10) 0.6407(2) 0.26052(13) 0.0196(3) Uani 1 1 d . . . H22 H 0.4200 0.6343 0.2844 0.023 Uiso 1 1 calc R . . C23 C 0.32695(10) 0.7348(2) 0.31732(14) 0.0225(4) Uani 1 1 d . . . H23 H 0.3541 0.7914 0.3782 0.027 Uiso 1 1 calc R . . C24 C 0.24964(10) 0.7441(2) 0.28454(14) 0.0227(4) Uani 1 1 d . . . H24 H 0.2233 0.8061 0.3235 0.027 Uiso 1 1 calc R . . C25 C 0.12897(10) 0.6744(2) 0.15564(16) 0.0282(4) Uani 1 1 d . . . H25 H 0.1021 0.7345 0.1949 0.034 Uiso 1 1 calc R . . C26 C 0.08997(11) 0.6019(3) 0.06429(18) 0.0344(5) Uani 1 1 d . . . H26 H 0.0366 0.6135 0.0398 0.041 Uiso 1 1 calc R . . C27 C 0.12873(11) 0.5099(3) 0.00622(17) 0.0330(5) Uani 1 1 d . . . H27 H 0.1013 0.4599 -0.0576 0.040 Uiso 1 1 calc R . . C28 C 0.20580(10) 0.4919(2) 0.04111(15) 0.0257(4) Uani 1 1 d . . . H28 H 0.2311 0.4276 0.0021 0.031 Uiso 1 1 calc R . . C29 C 0.24817(9) 0.56851(19) 0.13506(13) 0.0187(3) Uani 1 1 d . . . C30 C 0.20879(10) 0.6622(2) 0.19340(14) 0.0213(3) Uani 1 1 d . . . C31 C 0.36946(9) 0.4590(2) 0.10839(13) 0.0191(3) Uani 1 1 d . . . H31A H 0.3472 0.3543 0.1017 0.023 Uiso 1 1 calc R . . H31B H 0.3609 0.5020 0.0352 0.023 Uiso 1 1 calc R . . N31 N 0.45203(8) 0.44720(17) 0.15742(11) 0.0183(3) Uani 1 1 d . . . H31C H 0.4720 0.5433 0.1711 0.027 Uiso 1 1 calc R . . H31D H 0.4742 0.3978 0.1115 0.027 Uiso 1 1 calc R . . H31E H 0.4605 0.3932 0.2198 0.027 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 0.0194(6) 0.0259(6) 0.0205(6) 0.0033(5) 0.0055(5) -0.0003(5) O2 0.0234(6) 0.0243(6) 0.0195(6) 0.0027(5) 0.0100(5) 0.0034(5) C1 0.0189(8) 0.0161(7) 0.0192(8) 0.0018(6) 0.0073(6) 0.0001(6) C2 0.0231(8) 0.0190(8) 0.0171(7) -0.0015(6) 0.0051(6) -0.0035(6) C3 0.0258(9) 0.0182(8) 0.0185(8) -0.0027(6) 0.0070(6) -0.0018(6) C4 0.0247(8) 0.0156(7) 0.0178(7) 0.0011(6) 0.0095(6) 0.0011(6) C5 0.0307(9) 0.0206(8) 0.0209(8) -0.0004(7) 0.0111(7) 0.0042(7) C6 0.0276(9) 0.0229(8) 0.0261(9) 0.0030(7) 0.0135(7) 0.0059(7) C7 0.0227(8) 0.0219(8) 0.0224(8) 0.0038(7) 0.0101(6) 0.0020(6) C8 0.0193(8) 0.0301(10) 0.0339(10) 0.0027(8) 0.0096(7) 0.0017(7) C9 0.0190(8) 0.0359(11) 0.0360(11) -0.0019(9) 0.0058(7) -0.0028(7) C10 0.0243(9) 0.0309(10) 0.0303(10) -0.0060(8) 0.0066(7) -0.0062(7) C11 0.0226(8) 0.0232(8) 0.0217(8) -0.0021(7) 0.0080(6) -0.0037(6) C12 0.0254(9) 0.0239(9) 0.0230(8) -0.0066(7) 0.0075(7) -0.0035(7) C13 0.0228(8) 0.0200(8) 0.0228(8) -0.0048(7) 0.0094(6) -0.0011(6) C14 0.0190(7) 0.0161(7) 0.0168(7) 0.0016(6) 0.0072(6) -0.0005(6) C15 0.0193(7) 0.0167(7) 0.0172(7) 0.0016(6) 0.0076(6) 0.0008(6) C16 0.0206(8) 0.0183(8) 0.0198(8) 0.0023(6) 0.0084(6) -0.0008(6) C17 0.0185(7) 0.0163(7) 0.0195(8) -0.0010(6) 0.0071(6) -0.0029(6) C21 0.0195(8) 0.0169(7) 0.0182(7) 0.0023(6) 0.0068(6) 0.0003(6) C22 0.0205(8) 0.0198(8) 0.0193(8) 0.0019(6) 0.0067(6) 0.0003(6) C23 0.0283(9) 0.0210(8) 0.0200(8) -0.0002(7) 0.0096(7) 0.0012(7) C24 0.0290(9) 0.0200(8) 0.0227(8) 0.0024(7) 0.0133(7) 0.0046(7) C25 0.0215(9) 0.0305(10) 0.0362(10) 0.0070(8) 0.0140(7) 0.0032(7) C26 0.0175(8) 0.0392(11) 0.0461(12) 0.0060(10) 0.0074(8) 0.0012(8) C27 0.0234(9) 0.0369(11) 0.0353(11) -0.0011(9) 0.0016(8) -0.0046(8) C28 0.0237(9) 0.0267(9) 0.0265(9) -0.0023(7) 0.0062(7) -0.0013(7) C29 0.0188(8) 0.0169(7) 0.0213(8) 0.0028(6) 0.0068(6) 0.0002(6) C30 0.0220(8) 0.0202(8) 0.0242(8) 0.0055(7) 0.0107(7) 0.0023(6) C31 0.0177(8) 0.0210(8) 0.0183(8) -0.0015(6) 0.0046(6) 0.0014(6) N31 0.0186(7) 0.0198(7) 0.0177(6) 0.0013(5) 0.0068(5) 0.0015(5) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C17 1.253(2) . ? O2 C17 1.270(2) . ? C1 C2 1.398(2) . ? C1 C14 1.411(2) . ? C1 C17 1.510(2) . ? C2 C3 1.384(2) . ? C3 C4 1.399(2) . ? C4 C15 1.420(2) . ? C4 C5 1.437(2) . ? C5 C6 1.350(3) . ? C6 C7 1.433(3) . ? C7 C8 1.394(2) . ? C7 C16 1.430(2) . ? C8 C9 1.383(3) . ? C9 C10 1.393(3) . ? C10 C11 1.404(2) . ? C11 C16 1.417(2) . ? C11 C12 1.430(3) . ? C12 C13 1.354(2) . ? C13 C14 1.443(2) . ? C14 C15 1.428(2) . ? C15 C16 1.429(2) . ? C21 C22 1.374(2) . ? C21 C29 1.431(2) . ? C21 C31 1.510(2) . ? C22 C23 1.415(2) . ? C23 C24 1.369(2) . ? C24 C30 1.411(3) . ? C25 C26 1.363(3) . ? C25 C30 1.418(3) . ? C26 C27 1.408(3) . ? C27 C28 1.373(3) . ? C28 C29 1.423(2) . ? C29 C30 1.426(2) . ? C31 N31 1.481(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 C2 C1 C14 119.64(15) . . ? C2 C1 C17 118.60(15) . . ? C14 C1 C17 121.72(15) . . ? C3 C2 C1 121.60(16) . . ? C2 C3 C4 120.34(16) . . ? C3 C4 C15 119.29(15) . . ? C3 C4 C5 122.01(16) . . ? C15 C4 C5 118.70(16) . . ? C6 C5 C4 121.54(17) . . ? C5 C6 C7 121.48(16) . . ? C8 C7 C16 118.90(17) . . ? C8 C7 C6 122.76(16) . . ? C16 C7 C6 118.30(16) . . ? C9 C8 C7 121.37(17) . . ? C8 C9 C10 120.27(18) . . ? C9 C10 C11 120.52(18) . . ? C10 C11 C16 119.37(16) . . ? C10 C11 C12 122.31(17) . . ? C16 C11 C12 118.31(16) . . ? C13 C12 C11 122.12(17) . . ? C12 C13 C14 121.17(16) . . ? C1 C14 C15 118.91(15) . . ? C1 C14 C13 123.11(15) . . ? C15 C14 C13 117.93(15) . . ? C4 C15 C16 119.69(15) . . ? C4 C15 C14 120.12(15) . . ? C16 C15 C14 120.19(15) . . ? C11 C16 C15 120.27(15) . . ? C11 C16 C7 119.56(16) . . ? C15 C16 C7 120.17(16) . . ? O1 C17 O2 124.15(15) . . ? O1 C17 C1 117.20(14) . . ? O2 C17 C1 118.64(14) . . ? C22 C21 C29 119.38(15) . . ? C22 C21 C31 122.76(15) . . ? C29 C21 C31 117.85(14) . . ? C21 C22 C23 121.51(16) . . ? C24 C23 C22 119.97(16) . . ? C23 C24 C30 120.51(16) . . ? C26 C25 C30 121.48(18) . . ? C25 C26 C27 120.06(18) . . ? C28 C27 C26 120.47(19) . . ? C27 C28 C29 120.70(18) . . ? C28 C29 C30 118.67(15) . . ? C28 C29 C21 122.55(15) . . ? C30 C29 C21 118.76(15) . . ? C24 C30 C25 121.53(16) . . ? C24 C30 C29 119.85(16) . . ? C25 C30 C29 118.59(16) . . ? N31 C31 C21 113.51(13) . . ? _diffrn_measured_fraction_theta_max 0.825 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.962 _refine_diff_density_max 0.505 _refine_diff_density_min -0.275 _refine_diff_density_rms 0.075 #===END _database_code_depnum_ccdc_archive 'CCDC 933762'