# 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_imai102_1 #data_im9272a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H15 O2' _chemical_formula_weight 227.27 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' 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 6.0892(7) _cell_length_b 6.5384(7) _cell_length_c 16.9014(18) _cell_angle_alpha 80.756(2) _cell_angle_beta 84.572(2) _cell_angle_gamma 62.398(2) _cell_volume 588.42(11) _cell_formula_units_Z 2 _cell_measurement_temperature 115(2) _cell_measurement_reflns_used 2091 _cell_measurement_theta_min 2.44 _cell_measurement_theta_max 27.85 _exptl_crystal_description plate _exptl_crystal_colour red _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.283 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 242 _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 115(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX' _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 3660 _diffrn_reflns_av_R_equivalents 0.0163 _diffrn_reflns_av_sigmaI/netI 0.0441 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.44 _diffrn_reflns_theta_max 27.85 _reflns_number_total 2566 _reflns_number_gt 2091 _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^)+(0.0627P)^2^+0.1676P] 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 2566 _refine_ls_number_parameters 157 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0602 _refine_ls_R_factor_gt 0.0485 _refine_ls_wR_factor_ref 0.1279 _refine_ls_wR_factor_gt 0.1204 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.037 _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 1.0781(3) 0.0870(2) 0.20871(8) 0.0148(3) Uani 1 1 d . . . C2 C 0.9266(3) -0.0175(3) 0.23846(9) 0.0176(3) Uani 1 1 d . . . H2 H 0.9420 -0.1475 0.2158 0.021 Uiso 1 1 calc R . . C3 C 0.7546(3) 0.0637(3) 0.30018(9) 0.0188(3) Uani 1 1 d . . . H3 H 0.6535 -0.0099 0.3194 0.023 Uiso 1 1 calc R . . C4 C 0.7315(3) 0.2539(3) 0.33366(9) 0.0169(3) Uani 1 1 d . . . C5 C 0.8850(3) 0.3556(3) 0.30709(9) 0.0177(3) Uani 1 1 d . . . H5 H 0.8740 0.4815 0.3314 0.021 Uiso 1 1 calc R . . C6 C 1.0555(3) 0.2729(3) 0.24467(9) 0.0168(3) Uani 1 1 d . . . H6 H 1.1585 0.3451 0.2263 0.020 Uiso 1 1 calc R . . C7 C 1.2634(3) -0.0105(3) 0.13999(9) 0.0164(3) Uani 1 1 d . . . C8 C 1.4599(3) -0.2559(3) 0.17215(10) 0.0238(4) Uani 1 1 d . . . H8A H 1.5400 -0.2472 0.2183 0.036 Uiso 1 1 calc R . . H8B H 1.5847 -0.3200 0.1299 0.036 Uiso 1 1 calc R . . H8C H 1.3803 -0.3568 0.1887 0.036 Uiso 1 1 calc R . . C9 C 1.3992(3) 0.1360(3) 0.11016(9) 0.0227(4) Uani 1 1 d . . . H9A H 1.2783 0.2949 0.0902 0.034 Uiso 1 1 calc R . . H9B H 1.5164 0.0667 0.0668 0.034 Uiso 1 1 calc R . . H9C H 1.4895 0.1400 0.1544 0.034 Uiso 1 1 calc R . . C10 C 1.1250(3) -0.0101(3) 0.06850(8) 0.0148(3) Uani 1 1 d . . . C11 C 1.1805(3) -0.2097(3) 0.03471(9) 0.0168(3) Uani 1 1 d . . . H11 H 1.3041 -0.3558 0.0580 0.020 Uiso 1 1 calc R . . C12 C 0.9413(3) 0.1992(3) 0.03243(9) 0.0178(3) Uani 1 1 d . . . H12 H 0.8982 0.3385 0.0543 0.021 Uiso 1 1 calc R . . O4 O 0.5553(2) 0.33288(19) 0.39329(6) 0.0222(3) Uani 1 1 d . . . H4 H 0.5194 0.4716 0.3968 0.033 Uiso 1 1 calc R . . C21 C 0.2141(3) 0.8887(3) 0.45046(9) 0.0183(3) Uani 1 1 d . . . C22 C 0.0401(3) 0.7890(3) 0.47347(9) 0.0192(3) Uani 1 1 d . . . H22 H 0.0694 0.6499 0.4540 0.023 Uiso 1 1 calc R . . C23 C 0.1568(3) 1.1103(3) 0.47910(9) 0.0189(3) Uani 1 1 d . . . H23 H 0.2618 1.1818 0.4635 0.023 Uiso 1 1 calc R . . O21 O 0.4021(2) 0.79052(19) 0.40973(7) 0.0243(3) 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 C1 0.0153(7) 0.0157(7) 0.0120(7) -0.0014(5) -0.0023(5) -0.0055(6) C2 0.0204(7) 0.0175(7) 0.0159(7) -0.0031(6) -0.0020(6) -0.0090(6) C3 0.0197(7) 0.0202(8) 0.0178(8) -0.0014(6) -0.0004(6) -0.0106(6) C4 0.0159(7) 0.0173(8) 0.0135(7) -0.0014(6) -0.0006(5) -0.0043(6) C5 0.0194(7) 0.0147(7) 0.0170(7) -0.0030(6) -0.0024(6) -0.0056(6) C6 0.0168(7) 0.0172(8) 0.0161(7) -0.0002(6) -0.0013(6) -0.0081(6) C7 0.0148(7) 0.0189(8) 0.0146(7) -0.0044(6) 0.0006(6) -0.0063(6) C8 0.0198(8) 0.0255(9) 0.0205(8) -0.0057(6) -0.0049(6) -0.0040(7) C9 0.0225(8) 0.0331(9) 0.0184(8) -0.0076(7) 0.0035(6) -0.0171(7) C10 0.0144(7) 0.0181(7) 0.0124(7) -0.0037(5) 0.0033(5) -0.0079(6) C11 0.0162(7) 0.0141(7) 0.0176(7) -0.0009(6) -0.0005(6) -0.0053(6) C12 0.0207(7) 0.0155(7) 0.0180(7) -0.0046(6) 0.0023(6) -0.0088(6) O4 0.0218(6) 0.0213(6) 0.0214(6) -0.0074(5) 0.0072(4) -0.0080(5) C21 0.0199(7) 0.0186(8) 0.0145(7) -0.0021(6) 0.0018(6) -0.0075(6) C22 0.0237(8) 0.0169(8) 0.0187(8) -0.0045(6) 0.0006(6) -0.0102(6) C23 0.0194(8) 0.0181(8) 0.0204(8) -0.0016(6) -0.0004(6) -0.0098(6) O21 0.0226(6) 0.0234(6) 0.0243(6) -0.0072(5) 0.0085(5) -0.0087(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 C1 C6 1.390(2) . ? C1 C2 1.399(2) . ? C1 C7 1.5337(19) . ? C2 C3 1.387(2) . ? C3 C4 1.391(2) . ? C4 O4 1.3722(17) . ? C4 C5 1.385(2) . ? C5 C6 1.393(2) . ? C7 C9 1.535(2) . ? C7 C10 1.5362(19) . ? C7 C8 1.538(2) . ? C10 C11 1.3918(19) . ? C10 C12 1.392(2) . ? C11 C12 1.389(2) 2_755 ? C12 C11 1.389(2) 2_755 ? C21 O21 1.2280(18) . ? C21 C23 1.476(2) . ? C21 C22 1.476(2) . ? C22 C23 1.331(2) 2_576 ? C23 C22 1.331(2) 2_576 ? 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 C1 C2 117.64(13) . . ? C6 C1 C7 123.27(13) . . ? C2 C1 C7 119.07(13) . . ? C3 C2 C1 121.72(14) . . ? C2 C3 C4 119.39(14) . . ? O4 C4 C5 122.27(13) . . ? O4 C4 C3 117.74(13) . . ? C5 C4 C3 119.99(13) . . ? C4 C5 C6 119.84(14) . . ? C1 C6 C5 121.36(14) . . ? C1 C7 C9 112.27(12) . . ? C1 C7 C10 109.54(11) . . ? C9 C7 C10 107.24(12) . . ? C1 C7 C8 107.77(12) . . ? C9 C7 C8 107.42(12) . . ? C10 C7 C8 112.65(12) . . ? C11 C10 C12 117.08(13) . . ? C11 C10 C7 123.22(13) . . ? C12 C10 C7 119.63(13) . . ? C12 C11 C10 121.23(14) 2_755 . ? C11 C12 C10 121.68(13) 2_755 . ? O21 C21 C23 120.71(14) . . ? O21 C21 C22 121.56(14) . . ? C23 C21 C22 117.73(13) . . ? C23 C22 C21 121.44(14) 2_576 . ? C22 C23 C21 120.78(14) 2_576 . ? _diffrn_measured_fraction_theta_max 0.915 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.444 _refine_diff_density_min -0.251 _refine_diff_density_rms 0.051 _database_code_depnum_ccdc_archive 'CCDC 948644' ####################################################################### # # 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_imai102_2 #data_im9105a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H30 O3' _chemical_formula_weight 414.52 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' 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 6.5163(4) _cell_length_b 29.4058(19) _cell_length_c 11.3547(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.9990(10) _cell_angle_gamma 90.00 _cell_volume 2175.4(2) _cell_formula_units_Z 4 _cell_measurement_temperature 115(2) _cell_measurement_reflns_used 3776 _cell_measurement_theta_min 1.38 _cell_measurement_theta_max 27.85 _exptl_crystal_description plate _exptl_crystal_colour red _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.266 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 888 _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9685 _exptl_absorpt_correction_T_max 0.9960 _exptl_absorpt_process_details 'Bruker SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 115(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX' _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 19082 _diffrn_reflns_av_R_equivalents 0.0465 _diffrn_reflns_av_sigmaI/netI 0.0519 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -38 _diffrn_reflns_limit_k_max 37 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.38 _diffrn_reflns_theta_max 27.85 _reflns_number_total 5045 _reflns_number_gt 3776 _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^)+(0.0535P)^2^+0.8991P] 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 5045 _refine_ls_number_parameters 287 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0804 _refine_ls_R_factor_gt 0.0559 _refine_ls_wR_factor_ref 0.1298 _refine_ls_wR_factor_gt 0.1194 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.034 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.1648(3) -0.02815(6) 0.24020(15) 0.0179(4) Uani 1 1 d . . . C2 C 0.3633(3) -0.01133(6) 0.25169(15) 0.0184(4) Uani 1 1 d . . . H2 H 0.4636 -0.0278 0.2958 0.022 Uiso 1 1 calc R . . C3 C 0.4151(3) 0.02939(6) 0.19910(15) 0.0186(4) Uani 1 1 d . . . H3 H 0.5516 0.0404 0.2078 0.022 Uiso 1 1 calc R . . C4 C 0.2727(3) 0.05481(6) 0.13359(14) 0.0168(4) Uani 1 1 d . . . C5 C 0.0738(3) 0.03773(6) 0.12553(15) 0.0198(4) Uani 1 1 d . . . H5 H -0.0274 0.0544 0.0825 0.024 Uiso 1 1 calc R . . C6 C 0.0191(3) -0.00287(6) 0.17846(16) 0.0217(4) Uani 1 1 d . . . H6 H -0.1185 -0.0134 0.1724 0.026 Uiso 1 1 calc R . . C7 C 0.3448(3) 0.09681(6) 0.06563(15) 0.0186(4) Uani 1 1 d . . . C8 C 0.4921(3) 0.07948(6) -0.02942(16) 0.0243(4) Uani 1 1 d . . . H8A H 0.6157 0.0669 0.0086 0.036 Uiso 1 1 calc R . . H8B H 0.5305 0.1048 -0.0808 0.036 Uiso 1 1 calc R . . H8C H 0.4238 0.0558 -0.0764 0.036 Uiso 1 1 calc R . . C9 C 0.1674(3) 0.12133(6) 0.00162(17) 0.0252(4) Uani 1 1 d . . . H9A H 0.0990 0.1002 -0.0531 0.038 Uiso 1 1 calc R . . H9B H 0.2212 0.1473 -0.0423 0.038 Uiso 1 1 calc R . . H9C H 0.0686 0.1321 0.0594 0.038 Uiso 1 1 calc R . . C10 C 0.4498(3) 0.13153(6) 0.14874(15) 0.0179(4) Uani 1 1 d . . . C11 C 0.3594(3) 0.14334(6) 0.25445(15) 0.0211(4) Uani 1 1 d . . . H11 H 0.2366 0.1285 0.2768 0.025 Uiso 1 1 calc R . . C12 C 0.4445(3) 0.17638(6) 0.32854(15) 0.0210(4) Uani 1 1 d . . . H12 H 0.3785 0.1835 0.4002 0.025 Uiso 1 1 calc R . . C13 C 0.6242(3) 0.19923(6) 0.29975(15) 0.0170(4) Uani 1 1 d . . . C14 C 0.7143(3) 0.18717(6) 0.19424(16) 0.0216(4) Uani 1 1 d . . . H14 H 0.8376 0.2019 0.1720 0.026 Uiso 1 1 calc R . . C15 C 0.6293(3) 0.15417(6) 0.12000(16) 0.0221(4) Uani 1 1 d . . . H15 H 0.6953 0.1470 0.0484 0.026 Uiso 1 1 calc R . . C16 C 0.7281(3) 0.23403(6) 0.38224(15) 0.0181(4) Uani 1 1 d . . . C17 C 0.8953(3) 0.20890(6) 0.45383(16) 0.0242(4) Uani 1 1 d . . . H17A H 0.9653 0.2304 0.5070 0.036 Uiso 1 1 calc R . . H17B H 0.9951 0.1956 0.4001 0.036 Uiso 1 1 calc R . . H17C H 0.8323 0.1847 0.5001 0.036 Uiso 1 1 calc R . . C18 C 0.5787(3) 0.25455(6) 0.47159(16) 0.0226(4) Uani 1 1 d . . . H18A H 0.4661 0.2699 0.4292 0.034 Uiso 1 1 calc R . . H18B H 0.6519 0.2766 0.5216 0.034 Uiso 1 1 calc R . . H18C H 0.5230 0.2302 0.5207 0.034 Uiso 1 1 calc R . . C19 C 0.8182(3) 0.27333(6) 0.30996(14) 0.0167(4) Uani 1 1 d . . . C20 C 1.0215(3) 0.28744(6) 0.31908(15) 0.0197(4) Uani 1 1 d . . . H20 H 1.1133 0.2713 0.3698 0.024 Uiso 1 1 calc R . . C21 C 1.0944(3) 0.32440(6) 0.25619(16) 0.0207(4) Uani 1 1 d . . . H21 H 1.2343 0.3332 0.2638 0.025 Uiso 1 1 calc R . . C22 C 0.9624(3) 0.34850(6) 0.18222(15) 0.0182(4) Uani 1 1 d . . . C23 C 0.7589(3) 0.33519(6) 0.17057(15) 0.0187(4) Uani 1 1 d . . . H23 H 0.6675 0.3514 0.1198 0.022 Uiso 1 1 calc R . . C24 C 0.6898(3) 0.29797(6) 0.23365(14) 0.0176(4) Uani 1 1 d . . . H24 H 0.5504 0.2889 0.2246 0.021 Uiso 1 1 calc R . . O1 O 0.1055(2) -0.06859(4) 0.28907(11) 0.0232(3) Uani 1 1 d . . . H1 H 0.2089 -0.0821 0.3171 0.035 Uiso 1 1 calc R . . O22 O 1.04206(19) 0.38503(4) 0.12209(11) 0.0233(3) Uani 1 1 d . . . H22 H 0.9504 0.3964 0.0783 0.035 Uiso 1 1 calc R . . C31 C 1.1287(3) 0.03896(6) 0.48998(15) 0.0200(4) Uani 1 1 d . . . C32 C 0.9105(3) 0.04098(6) 0.44856(14) 0.0198(4) Uani 1 1 d . . . C33 C 0.7933(3) 0.00404(6) 0.46171(15) 0.0206(4) Uani 1 1 d . . . H33 H 0.6527 0.0058 0.4386 0.025 Uiso 1 1 calc R . . O31 O 1.2386(2) 0.07273(4) 0.48510(11) 0.0266(3) Uani 1 1 d . . . C34 C 0.8369(3) 0.08461(6) 0.39586(17) 0.0275(4) Uani 1 1 d . . . H34A H 0.6874 0.0835 0.3851 0.041 Uiso 1 1 calc R . . H34B H 0.9011 0.0891 0.3193 0.041 Uiso 1 1 calc R . . H34C H 0.8738 0.1098 0.4485 0.041 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(9) 0.0149(8) 0.0164(8) -0.0037(7) 0.0049(7) -0.0028(7) C2 0.0205(9) 0.0167(9) 0.0179(8) -0.0011(7) -0.0016(7) 0.0013(7) C3 0.0168(9) 0.0169(9) 0.0221(9) -0.0042(7) -0.0005(7) -0.0014(7) C4 0.0216(9) 0.0139(8) 0.0150(8) -0.0038(6) 0.0016(7) 0.0000(7) C5 0.0191(9) 0.0208(9) 0.0194(8) -0.0015(7) -0.0027(7) 0.0026(7) C6 0.0187(9) 0.0232(10) 0.0232(9) -0.0029(7) 0.0014(7) -0.0044(8) C7 0.0216(9) 0.0159(9) 0.0183(8) -0.0004(7) -0.0006(7) -0.0019(7) C8 0.0301(11) 0.0225(10) 0.0204(9) -0.0049(7) 0.0032(8) -0.0027(8) C9 0.0290(11) 0.0205(9) 0.0258(9) 0.0032(8) -0.0058(8) -0.0027(8) C10 0.0197(9) 0.0142(9) 0.0198(8) -0.0005(7) -0.0010(7) 0.0010(7) C11 0.0199(10) 0.0210(9) 0.0226(9) -0.0006(7) 0.0044(7) -0.0046(7) C12 0.0237(10) 0.0207(9) 0.0188(8) -0.0015(7) 0.0042(7) -0.0010(7) C13 0.0173(9) 0.0152(9) 0.0186(8) 0.0015(6) -0.0008(7) 0.0007(7) C14 0.0197(10) 0.0204(9) 0.0249(9) -0.0018(7) 0.0055(7) -0.0054(8) C15 0.0248(10) 0.0218(9) 0.0198(9) -0.0028(7) 0.0054(7) -0.0015(8) C16 0.0201(9) 0.0158(9) 0.0183(8) 0.0000(7) -0.0007(7) -0.0007(7) C17 0.0287(11) 0.0199(9) 0.0239(9) 0.0042(7) -0.0053(8) -0.0008(8) C18 0.0281(11) 0.0191(9) 0.0207(9) -0.0036(7) 0.0023(7) -0.0020(8) C19 0.0200(9) 0.0148(8) 0.0152(8) -0.0034(6) -0.0014(6) 0.0001(7) C20 0.0205(10) 0.0181(9) 0.0205(9) 0.0002(7) -0.0033(7) 0.0025(7) C21 0.0169(9) 0.0197(9) 0.0255(9) -0.0047(7) -0.0017(7) -0.0014(7) C22 0.0238(10) 0.0140(9) 0.0169(8) -0.0031(7) 0.0024(7) -0.0006(7) C23 0.0209(9) 0.0187(9) 0.0165(8) -0.0007(7) -0.0033(7) 0.0024(7) C24 0.0168(9) 0.0182(9) 0.0176(8) -0.0022(7) -0.0011(7) -0.0007(7) O1 0.0256(7) 0.0182(7) 0.0258(7) 0.0018(5) 0.0010(5) -0.0033(5) O22 0.0237(7) 0.0208(7) 0.0255(7) 0.0044(5) -0.0004(5) -0.0030(5) C31 0.0247(10) 0.0209(9) 0.0145(8) -0.0039(7) 0.0043(7) -0.0047(8) C32 0.0250(10) 0.0203(9) 0.0142(8) -0.0027(7) 0.0046(7) 0.0009(7) C33 0.0178(9) 0.0256(10) 0.0184(8) -0.0025(7) 0.0006(7) 0.0003(7) O31 0.0315(8) 0.0225(7) 0.0261(7) -0.0030(5) 0.0059(6) -0.0110(6) C34 0.0346(12) 0.0221(10) 0.0259(10) -0.0004(8) 0.0004(8) 0.0043(8) _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 C1 O1 1.371(2) . ? C1 C6 1.386(3) . ? C1 C2 1.388(2) . ? C2 C3 1.382(2) . ? C3 C4 1.396(2) . ? C4 C5 1.391(2) . ? C4 C7 1.534(2) . ? C5 C6 1.386(2) . ? C7 C9 1.535(2) . ? C7 C10 1.542(2) . ? C7 C8 1.544(2) . ? C10 C15 1.390(2) . ? C10 C11 1.390(2) . ? C11 C12 1.394(2) . ? C12 C13 1.394(2) . ? C13 C14 1.390(2) . ? C13 C16 1.537(2) . ? C14 C15 1.394(2) . ? C16 C17 1.537(2) . ? C16 C19 1.540(2) . ? C16 C18 1.542(2) . ? C19 C20 1.390(2) . ? C19 C24 1.397(2) . ? C20 C21 1.389(2) . ? C21 C22 1.386(2) . ? C22 O22 1.379(2) . ? C22 C23 1.387(2) . ? C23 C24 1.387(2) . ? C31 O31 1.226(2) . ? C31 C33 1.465(3) 3_756 ? C31 C32 1.491(3) . ? C32 C33 1.338(2) . ? C32 C34 1.491(2) . ? C33 C31 1.465(3) 3_756 ? 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 C1 C6 118.31(16) . . ? O1 C1 C2 122.67(16) . . ? C6 C1 C2 119.01(16) . . ? C3 C2 C1 120.15(16) . . ? C2 C3 C4 121.92(16) . . ? C5 C4 C3 116.83(16) . . ? C5 C4 C7 123.40(15) . . ? C3 C4 C7 119.51(15) . . ? C6 C5 C4 121.91(16) . . ? C5 C6 C1 120.15(17) . . ? C4 C7 C9 112.44(15) . . ? C4 C7 C10 111.20(13) . . ? C9 C7 C10 107.55(14) . . ? C4 C7 C8 106.59(14) . . ? C9 C7 C8 107.26(14) . . ? C10 C7 C8 111.80(15) . . ? C15 C10 C11 117.00(16) . . ? C15 C10 C7 122.68(15) . . ? C11 C10 C7 120.23(16) . . ? C10 C11 C12 121.70(17) . . ? C11 C12 C13 121.41(16) . . ? C14 C13 C12 116.67(16) . . ? C14 C13 C16 120.46(15) . . ? C12 C13 C16 122.77(15) . . ? C13 C14 C15 121.96(17) . . ? C10 C15 C14 121.26(16) . . ? C13 C16 C17 107.64(14) . . ? C13 C16 C19 110.06(13) . . ? C17 C16 C19 111.67(14) . . ? C13 C16 C18 112.64(14) . . ? C17 C16 C18 106.88(14) . . ? C19 C16 C18 107.95(14) . . ? C20 C19 C24 116.84(16) . . ? C20 C19 C16 123.78(15) . . ? C24 C19 C16 119.33(15) . . ? C21 C20 C19 121.95(16) . . ? C22 C21 C20 119.84(16) . . ? O22 C22 C21 117.61(16) . . ? O22 C22 C23 122.69(15) . . ? C21 C22 C23 119.70(16) . . ? C22 C23 C24 119.46(16) . . ? C23 C24 C19 122.20(16) . . ? O31 C31 C33 121.13(17) . 3_756 ? O31 C31 C32 120.51(17) . . ? C33 C31 C32 118.35(15) 3_756 . ? C33 C32 C34 124.28(17) . . ? C33 C32 C31 118.40(16) . . ? C34 C32 C31 117.32(16) . . ? C32 C33 C31 123.19(17) . 3_756 ? _diffrn_measured_fraction_theta_max 0.973 _diffrn_reflns_theta_full 27.85 _diffrn_measured_fraction_theta_full 0.973 _refine_diff_density_max 0.301 _refine_diff_density_min -0.235 _refine_diff_density_rms 0.050 _database_code_depnum_ccdc_archive 'CCDC 948645' ####################################################################### # # 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_imai102_3 #data_im9106a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C27.50 H28.50 Cl0.50 O3' _chemical_formula_weight 424.73 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' Cl Cl 0.1484 0.1585 '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 6.5284(5) _cell_length_b 29.274(2) _cell_length_c 11.3182(8) _cell_angle_alpha 90.00 _cell_angle_beta 91.0190(10) _cell_angle_gamma 90.00 _cell_volume 2162.7(3) _cell_formula_units_Z 4 _cell_measurement_temperature 115(2) _cell_measurement_reflns_used 3895 _cell_measurement_theta_min 1.39 _cell_measurement_theta_max 27.87 _exptl_crystal_description plate _exptl_crystal_colour red _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.304 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 904 _exptl_absorpt_coefficient_mu 0.143 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9452 _exptl_absorpt_correction_T_max 0.9929 _exptl_absorpt_process_details 'Bruker SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 115(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX' _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 18921 _diffrn_reflns_av_R_equivalents 0.0544 _diffrn_reflns_av_sigmaI/netI 0.0571 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -37 _diffrn_reflns_limit_k_max 37 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.39 _diffrn_reflns_theta_max 27.87 _reflns_number_total 4970 _reflns_number_gt 3895 _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^)+(0.0431P)^2^+1.6766P] 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 4970 _refine_ls_number_parameters 286 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0857 _refine_ls_R_factor_gt 0.0639 _refine_ls_wR_factor_ref 0.1368 _refine_ls_wR_factor_gt 0.1277 _refine_ls_goodness_of_fit_ref 1.089 _refine_ls_restrained_S_all 1.089 _refine_ls_shift/su_max 0.006 _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 0.2254(3) 0.05436(7) 0.36462(18) 0.0163(4) Uani 1 1 d . . . C2 C 0.0857(3) 0.02889(7) 0.29687(19) 0.0185(5) Uani 1 1 d . . . H2 H -0.0503 0.0399 0.2866 0.022 Uiso 1 1 calc R . . C3 C 0.1402(3) -0.01195(7) 0.24431(19) 0.0185(5) Uani 1 1 d . . . H3 H 0.0416 -0.0287 0.1993 0.022 Uiso 1 1 calc R . . C4 C 0.3391(3) -0.02847(7) 0.25730(18) 0.0177(4) Uani 1 1 d . . . C5 C 0.4818(3) -0.00332(7) 0.32120(19) 0.0202(5) Uani 1 1 d . . . H5 H 0.6189 -0.0139 0.3290 0.024 Uiso 1 1 calc R . . C6 C 0.4247(3) 0.03742(7) 0.37409(19) 0.0196(5) Uani 1 1 d . . . H6 H 0.5244 0.0543 0.4180 0.024 Uiso 1 1 calc R . . C7 C 0.1507(3) 0.09618(7) 0.43276(19) 0.0174(4) Uani 1 1 d . . . C8 C 0.0035(4) 0.07815(8) 0.5273(2) 0.0224(5) Uani 1 1 d . . . H8A H -0.1196 0.0656 0.4886 0.034 Uiso 1 1 calc R . . H8B H -0.0352 0.1032 0.5797 0.034 Uiso 1 1 calc R . . H8C H 0.0719 0.0541 0.5737 0.034 Uiso 1 1 calc R . . C9 C 0.3272(4) 0.12076(7) 0.4985(2) 0.0237(5) Uani 1 1 d . . . H9A H 0.3934 0.0996 0.5543 0.035 Uiso 1 1 calc R . . H9B H 0.2729 0.1470 0.5418 0.035 Uiso 1 1 calc R . . H9C H 0.4276 0.1314 0.4414 0.035 Uiso 1 1 calc R . . C10 C 0.0466(3) 0.13101(7) 0.34959(18) 0.0160(4) Uani 1 1 d . . . C11 C 0.1391(3) 0.14349(7) 0.24464(19) 0.0196(5) Uani 1 1 d . . . H11 H 0.2632 0.1290 0.2231 0.024 Uiso 1 1 calc R . . C12 C 0.0546(3) 0.17660(7) 0.17059(19) 0.0194(5) Uani 1 1 d . . . H12 H 0.1221 0.1842 0.0996 0.023 Uiso 1 1 calc R . . C13 C -0.1268(3) 0.19888(7) 0.19817(18) 0.0154(4) Uani 1 1 d . . . C14 C -0.2194(3) 0.18624(7) 0.30299(19) 0.0198(5) Uani 1 1 d . . . H14 H -0.3440 0.2005 0.3244 0.024 Uiso 1 1 calc R . . C15 C -0.1339(3) 0.15318(7) 0.37731(19) 0.0200(5) Uani 1 1 d . . . H15 H -0.2007 0.1457 0.4486 0.024 Uiso 1 1 calc R . . C16 C -0.2311(3) 0.23391(7) 0.11535(19) 0.0163(4) Uani 1 1 d . . . C17 C -0.3968(3) 0.20840(7) 0.0426(2) 0.0214(5) Uani 1 1 d . . . H17A H -0.3328 0.1840 -0.0031 0.032 Uiso 1 1 calc R . . H17B H -0.4659 0.2298 -0.0113 0.032 Uiso 1 1 calc R . . H17C H -0.4971 0.1951 0.0961 0.032 Uiso 1 1 calc R . . C18 C -0.0812(3) 0.25459(7) 0.02655(19) 0.0207(5) Uani 1 1 d . . . H18A H 0.0282 0.2709 0.0695 0.031 Uiso 1 1 calc R . . H18B H -0.1548 0.2760 -0.0256 0.031 Uiso 1 1 calc R . . H18C H -0.0214 0.2301 -0.0208 0.031 Uiso 1 1 calc R . . C19 C -0.3218(3) 0.27311(7) 0.18767(18) 0.0160(4) Uani 1 1 d . . . C20 C -0.1948(3) 0.29778(7) 0.26532(18) 0.0164(4) Uani 1 1 d . . . H20 H -0.0556 0.2888 0.2748 0.020 Uiso 1 1 calc R . . C21 C -0.2655(3) 0.33477(7) 0.32878(19) 0.0177(4) Uani 1 1 d . . . H21 H -0.1756 0.3512 0.3803 0.021 Uiso 1 1 calc R . . C22 C -0.4688(3) 0.34762(7) 0.31631(18) 0.0173(4) Uani 1 1 d . . . C23 C -0.5986(3) 0.32398(7) 0.2406(2) 0.0197(5) Uani 1 1 d . . . H23 H -0.7379 0.3330 0.2318 0.024 Uiso 1 1 calc R . . C24 C -0.5247(3) 0.28698(7) 0.17731(19) 0.0187(5) Uani 1 1 d . . . H24 H -0.6152 0.2708 0.1257 0.022 Uiso 1 1 calc R . . O4 O 0.4004(2) -0.06889(5) 0.20841(14) 0.0223(4) Uani 1 1 d . . . H4 H 0.2976 -0.0830 0.1818 0.033 Uiso 1 1 calc R . . O22 O -0.5505(2) 0.38396(5) 0.37770(14) 0.0236(4) Uani 1 1 d . . . H22 H -0.4597 0.3954 0.4220 0.035 Uiso 1 1 calc R . . C31 C -0.3650(3) -0.03845(7) -0.00982(19) 0.0203(5) Uani 1 1 d . . . C32 C -0.2945(3) 0.00521(7) 0.03987(19) 0.0201(5) Uani 1 1 d . . . H32 H -0.1550 0.0081 0.0641 0.024 Uiso 1 1 calc R . . C33 C -0.4181(3) 0.04100(7) 0.05245(18) 0.0188(5) Uani 1 1 d D . . O31 O -0.2522(3) -0.07169(5) -0.01459(14) 0.0267(4) Uani 1 1 d . . . Cl33 Cl -0.3438(2) 0.09045(5) 0.11437(15) 0.0207(3) Uiso 0.50 1 d P . . C33M C -0.352(2) 0.0872(4) 0.1044(13) 0.099(6) Uiso 0.50 1 d PD . . H33A H -0.4204 0.0922 0.1796 0.149 Uiso 0.50 1 calc PR . . H33B H -0.3897 0.1117 0.0490 0.149 Uiso 0.50 1 calc PR . . H33C H -0.2031 0.0874 0.1176 0.149 Uiso 0.50 1 calc PR . . 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 0.0200(11) 0.0137(10) 0.0153(10) 0.0037(8) 0.0023(8) -0.0008(8) C2 0.0150(10) 0.0163(10) 0.0242(12) 0.0030(9) 0.0006(9) 0.0013(8) C3 0.0209(11) 0.0170(11) 0.0177(11) 0.0022(8) -0.0017(8) -0.0015(8) C4 0.0238(11) 0.0128(10) 0.0166(11) 0.0045(8) 0.0049(8) 0.0015(8) C5 0.0163(11) 0.0220(11) 0.0222(12) 0.0025(9) 0.0007(9) 0.0032(9) C6 0.0187(11) 0.0202(11) 0.0199(11) 0.0013(9) -0.0017(9) -0.0020(9) C7 0.0204(11) 0.0149(10) 0.0169(11) 0.0012(8) 0.0012(8) 0.0004(8) C8 0.0278(12) 0.0203(11) 0.0195(11) 0.0031(9) 0.0057(9) 0.0050(9) C9 0.0282(12) 0.0179(11) 0.0247(12) -0.0014(9) -0.0046(10) 0.0022(9) C10 0.0171(10) 0.0129(10) 0.0180(11) 0.0009(8) -0.0009(8) -0.0017(8) C11 0.0165(11) 0.0203(11) 0.0223(12) -0.0008(9) 0.0055(9) 0.0028(8) C12 0.0204(11) 0.0199(11) 0.0181(11) 0.0028(8) 0.0065(9) -0.0002(9) C13 0.0177(10) 0.0118(10) 0.0166(10) -0.0009(8) -0.0001(8) -0.0018(8) C14 0.0188(11) 0.0186(11) 0.0223(12) 0.0017(9) 0.0053(9) 0.0033(9) C15 0.0241(11) 0.0191(11) 0.0171(11) 0.0035(8) 0.0057(9) 0.0004(9) C16 0.0157(10) 0.0160(10) 0.0173(11) 0.0007(8) 0.0002(8) -0.0010(8) C17 0.0231(12) 0.0183(11) 0.0225(12) -0.0034(9) -0.0035(9) 0.0012(9) C18 0.0263(12) 0.0167(11) 0.0192(11) 0.0019(8) 0.0032(9) 0.0028(9) C19 0.0196(11) 0.0130(10) 0.0153(10) 0.0038(8) 0.0000(8) -0.0015(8) C20 0.0153(10) 0.0152(10) 0.0188(11) 0.0037(8) -0.0016(8) 0.0013(8) C21 0.0204(11) 0.0154(10) 0.0171(11) 0.0001(8) -0.0015(8) -0.0036(8) C22 0.0239(11) 0.0121(10) 0.0161(11) 0.0018(8) 0.0052(8) 0.0018(8) C23 0.0156(10) 0.0185(11) 0.0249(12) 0.0031(9) 0.0007(9) 0.0031(8) C24 0.0168(11) 0.0174(11) 0.0220(11) 0.0002(9) -0.0011(8) -0.0020(8) O4 0.0245(8) 0.0177(8) 0.0247(9) -0.0006(6) 0.0026(7) 0.0026(6) O22 0.0251(9) 0.0185(8) 0.0272(9) -0.0050(6) 0.0006(7) 0.0039(6) C31 0.0265(12) 0.0205(11) 0.0142(11) 0.0040(8) 0.0040(9) 0.0049(9) C32 0.0185(11) 0.0237(12) 0.0183(11) 0.0032(9) 0.0006(8) 0.0005(9) C33 0.0260(12) 0.0165(11) 0.0141(11) 0.0015(8) 0.0021(9) -0.0021(9) O31 0.0316(9) 0.0218(8) 0.0270(9) 0.0031(7) 0.0044(7) 0.0090(7) _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 C1 C6 1.395(3) . ? C1 C2 1.396(3) . ? C1 C7 1.531(3) . ? C2 C3 1.385(3) . ? C3 C4 1.391(3) . ? C4 O4 1.369(2) . ? C4 C5 1.381(3) . ? C5 C6 1.388(3) . ? C7 C10 1.538(3) . ? C7 C9 1.539(3) . ? C7 C8 1.544(3) . ? C10 C15 1.386(3) . ? C10 C11 1.391(3) . ? C11 C12 1.389(3) . ? C12 C13 1.392(3) . ? C13 C14 1.391(3) . ? C13 C16 1.540(3) . ? C14 C15 1.393(3) . ? C16 C19 1.534(3) . ? C16 C18 1.539(3) . ? C16 C17 1.541(3) . ? C19 C24 1.388(3) . ? C19 C20 1.398(3) . ? C20 C21 1.383(3) . ? C21 C22 1.384(3) . ? C22 C23 1.380(3) . ? C22 O22 1.383(2) . ? C23 C24 1.390(3) . ? C31 O31 1.222(3) . ? C31 C32 1.467(3) . ? C31 C33 1.490(3) 3_455 ? C32 C33 1.332(3) . ? C33 C31 1.490(3) 3_455 ? C33 C33M 1.535(8) . ? C33 Cl33 1.676(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 C1 C2 116.84(19) . . ? C6 C1 C7 123.39(18) . . ? C2 C1 C7 119.53(18) . . ? C3 C2 C1 121.80(19) . . ? C2 C3 C4 120.07(19) . . ? O4 C4 C5 118.23(19) . . ? O4 C4 C3 122.47(19) . . ? C5 C4 C3 119.30(19) . . ? C4 C5 C6 120.01(19) . . ? C5 C6 C1 121.9(2) . . ? C1 C7 C10 111.28(17) . . ? C1 C7 C9 112.02(17) . . ? C10 C7 C9 107.76(17) . . ? C1 C7 C8 106.46(17) . . ? C10 C7 C8 112.18(17) . . ? C9 C7 C8 107.12(18) . . ? C15 C10 C11 117.00(19) . . ? C15 C10 C7 122.68(19) . . ? C11 C10 C7 120.21(19) . . ? C12 C11 C10 121.6(2) . . ? C11 C12 C13 121.5(2) . . ? C14 C13 C12 116.81(19) . . ? C14 C13 C16 120.13(19) . . ? C12 C13 C16 122.97(19) . . ? C13 C14 C15 121.6(2) . . ? C10 C15 C14 121.5(2) . . ? C19 C16 C18 108.07(17) . . ? C19 C16 C13 110.12(17) . . ? C18 C16 C13 112.34(17) . . ? C19 C16 C17 111.91(17) . . ? C18 C16 C17 106.88(17) . . ? C13 C16 C17 107.51(16) . . ? C24 C19 C20 117.14(19) . . ? C24 C19 C16 123.40(18) . . ? C20 C19 C16 119.41(18) . . ? C21 C20 C19 122.07(19) . . ? C20 C21 C22 119.21(19) . . ? C23 C22 O22 117.35(19) . . ? C23 C22 C21 120.27(19) . . ? O22 C22 C21 122.38(19) . . ? C22 C23 C24 119.71(19) . . ? C19 C24 C23 121.59(19) . . ? O31 C31 C32 121.7(2) . . ? O31 C31 C33 121.0(2) . 3_455 ? C32 C31 C33 117.23(19) . 3_455 ? C33 C32 C31 122.7(2) . . ? C32 C33 C31 120.0(2) . 3_455 ? C32 C33 C33M 124.6(6) . . ? C31 C33 C33M 115.4(6) 3_455 . ? C32 C33 Cl33 123.55(18) . . ? C31 C33 Cl33 116.44(17) 3_455 . ? C33M C33 Cl33 2.3(6) . . ? _diffrn_measured_fraction_theta_max 0.962 _diffrn_reflns_theta_full 27.87 _diffrn_measured_fraction_theta_full 0.962 _refine_diff_density_max 0.527 _refine_diff_density_min -0.530 _refine_diff_density_rms 0.056 _database_code_depnum_ccdc_archive 'CCDC 948646'