Supplementary Material (ESI) for Chemical Communications This journal is © The Royal Society of Chemistry 2001 data_global _journal_coden_Cambridge 182 _publ_requested_journal 'Chemical Communications' loop_ _publ_author_name 'Kumar, V. S. Senthil' 'Nangia, Ashwini' _publ_contact_author_name 'Ashwini Nangia' _publ_contact_author_address ; School of Chemistry University of Hyderabad Hyderabad 500 046 INDIA ; _publ_contact_author_email 'ANSC@UOHYD.ERNET.IN' _publ_section_title ; Inclusion adducts of 4,4-bis(4'-biphenylyl)-2,5-cyclohexadienone: a clay mimic organic host ; data_dmoe _database_code_CSD 172238 _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common 4,4-bis(4'-biphenyl)-2,5-cyclohexadienone _chemical_melting_point '128 C' _chemical_formula_moiety '(C30 H22 O) (C4 H10 O2)0.5' _chemical_formula_sum 'C32 H27 O2' _chemical_formula_weight 443.54 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 C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 25.464(5) _cell_length_b 19.751(4) _cell_length_c 9.770(2) _cell_angle_alpha 90.00 _cell_angle_beta 97.72(3) _cell_angle_gamma 90.00 _cell_volume 4868.9(17) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.210 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1880 _exptl_absorpt_coefficient_mu 0.074 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11573 _diffrn_reflns_av_R_equivalents 0.0728 _diffrn_reflns_av_sigmaI/netI 0.1051 _diffrn_reflns_limit_h_min -33 _diffrn_reflns_limit_h_max 32 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.61 _diffrn_reflns_theta_max 28.03 _reflns_number_total 5886 _reflns_number_gt 1352 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0618P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0008(2) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 5886 _refine_ls_number_parameters 308 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2224 _refine_ls_R_factor_gt 0.0522 _refine_ls_wR_factor_ref 0.2060 _refine_ls_wR_factor_gt 0.1077 _refine_ls_goodness_of_fit_ref 1.000 _refine_ls_restrained_S_all 1.000 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicit _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C4 C 0.45053(13) 0.19420(17) 0.4902(3) 0.0486(8) Uani 1 1 d . . . C23 C 0.56083(15) 0.32226(18) 0.6005(4) 0.0645(11) Uani 1 1 d . . . H23A H 0.5634 0.3660 0.6361 0.077 Uiso 1 1 calc R . . O1 O 0.43270(12) -0.01450(15) 0.5234(4) 0.1056(12) Uani 1 1 d . . . C21 C 0.60044(14) 0.22253(18) 0.5324(4) 0.0552(9) Uani 1 1 d . . . H21A H 0.6303 0.1976 0.5191 0.066 Uiso 1 1 calc R . . C25 C 0.65946(15) 0.31836(18) 0.6201(4) 0.0542(9) Uani 1 1 d . . . C10 C 0.31988(14) 0.33329(17) 0.3731(4) 0.0518(9) Uani 1 1 d . . . C20 C 0.55114(14) 0.19333(18) 0.5009(4) 0.0581(10) Uani 1 1 d . . . H20A H 0.5486 0.1488 0.4695 0.070 Uiso 1 1 calc R . . C5 C 0.44796(14) 0.14552(19) 0.3706(4) 0.0608(10) Uani 1 1 d . . . H5A H 0.4504 0.1633 0.2836 0.073 Uiso 1 1 calc R . . C22 C 0.60690(14) 0.28791(18) 0.5831(4) 0.0553(9) Uani 1 1 d . . . C3 C 0.44564(13) 0.15733(19) 0.6226(4) 0.0566(9) Uani 1 1 d . . . H3A H 0.4454 0.1830 0.7024 0.068 Uiso 1 1 calc R . . C19 C 0.50536(14) 0.22878(17) 0.5151(3) 0.0502(9) Uani 1 1 d . . . C11 C 0.36338(14) 0.33123(19) 0.3018(4) 0.0643(11) Uani 1 1 d . . . H11A H 0.3644 0.3594 0.2259 0.077 Uiso 1 1 calc R . . C7 C 0.40534(13) 0.24541(17) 0.4546(3) 0.0501(9) Uani 1 1 d . . . C6 C 0.44250(15) 0.0796(2) 0.3812(5) 0.0704(12) Uani 1 1 d . . . H6A H 0.4412 0.0533 0.3020 0.084 Uiso 1 1 calc R . . C18 C 0.24075(15) 0.3996(2) 0.4199(4) 0.0678(11) Uani 1 1 d . . . H18A H 0.2499 0.3912 0.5138 0.081 Uiso 1 1 calc R . . C26 C 0.70526(16) 0.2806(2) 0.6453(4) 0.0680(11) Uani 1 1 d . . . H26A H 0.7027 0.2337 0.6376 0.082 Uiso 1 1 calc R . . C1 C 0.43845(15) 0.0464(2) 0.5124(5) 0.0731(12) Uani 1 1 d . . . C2 C 0.44173(14) 0.09099(19) 0.6329(4) 0.0653(11) Uani 1 1 d . . . H2A H 0.4410 0.0719 0.7197 0.078 Uiso 1 1 calc R . . C8 C 0.36223(14) 0.24773(18) 0.5262(4) 0.0563(9) Uani 1 1 d . . . H8A H 0.3615 0.2199 0.6027 0.068 Uiso 1 1 calc R . . C27 C 0.75441(16) 0.3086(2) 0.6812(4) 0.0764(12) Uani 1 1 d . . . H27A H 0.7842 0.2809 0.6955 0.092 Uiso 1 1 calc R . . C12 C 0.40499(15) 0.28832(18) 0.3416(4) 0.0609(10) Uani 1 1 d . . . H12A H 0.4337 0.2879 0.2918 0.073 Uiso 1 1 calc R . . C24 C 0.51151(15) 0.29413(18) 0.5669(4) 0.0635(11) Uani 1 1 d . . . H24A H 0.4816 0.3193 0.5791 0.076 Uiso 1 1 calc R . . C13 C 0.27303(14) 0.37555(18) 0.3278(4) 0.0558(9) Uani 1 1 d . . . C9 C 0.31998(15) 0.29094(19) 0.4858(4) 0.0630(10) Uani 1 1 d . . . H9A H 0.2913 0.2914 0.5354 0.076 Uiso 1 1 calc R . . C30 C 0.66633(16) 0.3875(2) 0.6356(4) 0.0736(12) Uani 1 1 d . . . H30A H 0.6368 0.4155 0.6202 0.088 Uiso 1 1 calc R . . C16 C 0.18095(17) 0.4483(2) 0.2368(6) 0.0820(14) Uani 1 1 d . . . H16A H 0.1498 0.4715 0.2060 0.098 Uiso 1 1 calc R . . C29 C 0.71542(19) 0.4164(2) 0.6730(5) 0.0850(14) Uani 1 1 d . . . H29A H 0.7184 0.4631 0.6829 0.102 Uiso 1 1 calc R . . C28 C 0.75973(18) 0.3770(2) 0.6958(4) 0.0783(13) Uani 1 1 d . . . H28A H 0.7929 0.3964 0.7209 0.094 Uiso 1 1 calc R . . C17 C 0.19522(17) 0.4358(2) 0.3755(6) 0.0813(13) Uani 1 1 d . . . H17A H 0.1742 0.4518 0.4393 0.098 Uiso 1 1 calc R . . C15 C 0.21304(18) 0.4261(2) 0.1453(5) 0.0808(13) Uani 1 1 d . . . H15A H 0.2040 0.4356 0.0518 0.097 Uiso 1 1 calc R . . C14 C 0.25856(16) 0.39004(19) 0.1884(4) 0.0702(11) Uani 1 1 d . . . H14A H 0.2798 0.3753 0.1239 0.084 Uiso 1 1 calc R . . O2 O 0.5516(3) 0.4738(3) 0.8015(7) 0.236(3) Uani 1 1 d . . . C32 C 0.5236(4) 0.5264(3) 0.8051(13) 0.229(8) Uani 1 1 d . . . H32A H 0.5452 0.5659 0.7934 0.275 Uiso 1 1 calc R . . H32B H 0.5116 0.5297 0.8949 0.275 Uiso 1 1 calc R . . C31 C 0.5947(3) 0.4671(4) 0.9054(9) 0.201(4) Uani 1 1 d . . . H31A H 0.6130 0.4255 0.8926 0.301 Uiso 1 1 calc R . . H31B H 0.5823 0.4666 0.9939 0.301 Uiso 1 1 calc R . . H31C H 0.6185 0.5045 0.9011 0.301 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 C4 0.057(2) 0.049(2) 0.0402(19) 0.0035(17) 0.0075(16) -0.0013(17) C23 0.070(3) 0.051(2) 0.072(3) -0.010(2) 0.009(2) -0.003(2) O1 0.105(2) 0.0557(19) 0.152(3) 0.000(2) 0.001(2) -0.0114(16) C21 0.056(2) 0.056(2) 0.056(2) 0.0017(19) 0.0172(19) 0.0086(18) C25 0.057(2) 0.058(2) 0.049(2) 0.0016(19) 0.0101(18) -0.0023(19) C10 0.052(2) 0.058(2) 0.046(2) -0.0026(18) 0.0063(17) 0.0017(18) C20 0.066(2) 0.051(2) 0.058(2) -0.0037(19) 0.012(2) -0.0015(19) C5 0.060(2) 0.071(3) 0.051(2) -0.009(2) 0.0028(19) -0.001(2) C22 0.060(2) 0.050(2) 0.057(2) 0.0038(18) 0.0125(19) -0.0019(19) C3 0.053(2) 0.063(2) 0.053(2) 0.006(2) 0.0060(18) -0.0008(19) C19 0.058(2) 0.048(2) 0.045(2) 0.0012(17) 0.0096(17) 0.0015(17) C11 0.064(2) 0.072(3) 0.058(2) 0.017(2) 0.015(2) 0.009(2) C7 0.056(2) 0.052(2) 0.042(2) 0.0031(17) 0.0057(17) 0.0038(17) C6 0.069(3) 0.060(3) 0.082(3) -0.014(2) 0.008(2) -0.004(2) C18 0.057(2) 0.083(3) 0.065(3) -0.006(2) 0.012(2) -0.002(2) C26 0.067(3) 0.066(3) 0.071(3) 0.008(2) 0.011(2) 0.002(2) C1 0.053(2) 0.056(3) 0.108(4) -0.005(3) 0.002(2) -0.002(2) C2 0.059(2) 0.063(3) 0.073(3) 0.019(2) 0.005(2) -0.006(2) C8 0.056(2) 0.070(2) 0.043(2) 0.0102(19) 0.0072(18) -0.004(2) C27 0.060(3) 0.093(3) 0.074(3) 0.015(3) -0.002(2) 0.000(2) C12 0.060(2) 0.073(3) 0.052(2) 0.006(2) 0.0190(19) 0.004(2) C24 0.061(2) 0.056(2) 0.074(3) -0.006(2) 0.012(2) 0.005(2) C13 0.054(2) 0.057(2) 0.056(2) -0.0045(19) 0.0062(19) -0.0038(19) C9 0.059(2) 0.081(3) 0.050(2) 0.003(2) 0.0123(19) -0.002(2) C30 0.063(3) 0.070(3) 0.088(3) -0.007(2) 0.008(2) -0.005(2) C16 0.062(3) 0.078(3) 0.104(4) 0.009(3) 0.005(3) 0.009(2) C29 0.082(3) 0.074(3) 0.098(4) -0.011(3) 0.009(3) -0.018(3) C28 0.071(3) 0.097(3) 0.067(3) 0.002(3) 0.008(2) -0.024(3) C17 0.059(3) 0.085(3) 0.104(4) -0.010(3) 0.026(3) 0.000(2) C15 0.079(3) 0.083(3) 0.077(3) 0.011(3) 0.001(3) 0.010(3) C14 0.070(3) 0.072(3) 0.069(3) 0.009(2) 0.010(2) 0.010(2) O2 0.270(8) 0.207(6) 0.205(6) -0.090(5) -0.062(5) 0.067(5) C32 0.267(17) 0.126(6) 0.32(2) -0.078(8) 0.136(14) 0.004(6) C31 0.218(9) 0.214(9) 0.160(8) -0.067(7) -0.014(7) 0.001(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C4 C3 1.504(4) . ? C4 C5 1.508(4) . ? C4 C7 1.536(4) . ? C4 C19 1.544(4) . ? C23 C24 1.372(5) . ? C23 C22 1.385(5) . ? O1 C1 1.218(4) . ? C21 C20 1.378(5) . ? C21 C22 1.385(4) . ? C25 C26 1.379(5) . ? C25 C30 1.383(5) . ? C25 C22 1.467(5) . ? C10 C9 1.382(5) . ? C10 C11 1.386(4) . ? C10 C13 1.474(5) . ? C20 C19 1.383(4) . ? C5 C6 1.314(5) . ? C3 C2 1.319(4) . ? C19 C24 1.388(4) . ? C11 C12 1.372(5) . ? C7 C8 1.379(4) . ? C7 C12 1.391(4) . ? C6 C1 1.456(6) . ? C18 C13 1.382(5) . ? C18 C17 1.382(5) . ? C26 C27 1.371(5) . ? C1 C2 1.463(5) . ? C8 C9 1.388(5) . ? C27 C28 1.363(5) . ? C13 C14 1.392(5) . ? C30 C29 1.378(5) . ? C16 C15 1.362(6) . ? C16 C17 1.377(6) . ? C29 C28 1.364(6) . ? C15 C14 1.378(5) . ? O2 C32 1.263(7) . ? O2 C31 1.399(8) . ? C32 C32 1.503(19) 2_656 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C3 C4 C5 111.0(3) . . ? C3 C4 C7 111.6(3) . . ? C5 C4 C7 106.9(3) . . ? C3 C4 C19 104.8(3) . . ? C5 C4 C19 110.4(3) . . ? C7 C4 C19 112.2(3) . . ? C24 C23 C22 122.4(4) . . ? C20 C21 C22 122.1(3) . . ? C26 C25 C30 115.1(4) . . ? C26 C25 C22 122.9(4) . . ? C30 C25 C22 122.0(4) . . ? C9 C10 C11 117.8(3) . . ? C9 C10 C13 119.8(3) . . ? C11 C10 C13 122.3(3) . . ? C21 C20 C19 121.4(3) . . ? C6 C5 C4 124.4(4) . . ? C23 C22 C21 116.0(3) . . ? C23 C22 C25 121.9(3) . . ? C21 C22 C25 122.1(3) . . ? C2 C3 C4 124.2(4) . . ? C20 C19 C24 116.9(3) . . ? C20 C19 C4 121.1(3) . . ? C24 C19 C4 121.6(3) . . ? C12 C11 C10 121.0(4) . . ? C8 C7 C12 117.5(3) . . ? C8 C7 C4 122.0(3) . . ? C12 C7 C4 120.4(3) . . ? C5 C6 C1 122.4(4) . . ? C13 C18 C17 121.4(4) . . ? C27 C26 C25 123.3(4) . . ? O1 C1 C6 123.1(4) . . ? O1 C1 C2 121.2(5) . . ? C6 C1 C2 115.7(4) . . ? C3 C2 C1 122.2(4) . . ? C7 C8 C9 121.0(3) . . ? C28 C27 C26 120.1(4) . . ? C11 C12 C7 121.6(3) . . ? C23 C24 C19 121.2(4) . . ? C18 C13 C14 117.6(4) . . ? C18 C13 C10 121.8(4) . . ? C14 C13 C10 120.5(4) . . ? C10 C9 C8 121.1(4) . . ? C29 C30 C25 122.3(4) . . ? C15 C16 C17 119.1(4) . . ? C28 C29 C30 120.5(4) . . ? C27 C28 C29 118.7(4) . . ? C16 C17 C18 120.1(4) . . ? C16 C15 C14 121.3(5) . . ? C15 C14 C13 120.4(4) . . ? C32 O2 C31 116.6(8) . . ? O2 C32 C32 112.3(8) . 2_656 ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 28.03 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.179 _refine_diff_density_min -0.194 _refine_diff_density_rms 0.039 data_hexane _database_code_CSD 172239 _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common 4,4-bis(4'-biphenyl)-2,5-cyclohexadienone _chemical_melting_point '128 C' _chemical_formula_moiety '(C30 H22 O) (C6 H14)0.5' _chemical_formula_sum 'C33 H29 O' _chemical_formula_weight 441.56 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 C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 25.052(5) _cell_length_b 20.185(4) _cell_length_c 9.7224(19) _cell_angle_alpha 90.00 _cell_angle_beta 98.27(3) _cell_angle_gamma 90.00 _cell_volume 4865.4(17) _cell_formula_units_Z 8 _cell_measurement_temperature 168(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.206 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1880 _exptl_absorpt_coefficient_mu 0.071 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 168(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16694 _diffrn_reflns_av_R_equivalents 0.0472 _diffrn_reflns_av_sigmaI/netI 0.1043 _diffrn_reflns_limit_h_min -30 _diffrn_reflns_limit_h_max 31 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -4 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.93 _diffrn_reflns_theta_max 26.41 _reflns_number_total 4736 _reflns_number_gt 2282 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1057P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4736 _refine_ls_number_parameters 317 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1208 _refine_ls_R_factor_gt 0.0675 _refine_ls_wR_factor_ref 0.1825 _refine_ls_wR_factor_gt 0.1716 _refine_ls_goodness_of_fit_ref 0.890 _refine_ls_restrained_S_all 0.890 _refine_ls_shift/su_max 0.005 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicit _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C22 C 0.39010(12) 0.21394(14) 0.4171(3) 0.0312(7) Uani 1 1 d . . . C19 C 0.49312(12) 0.27418(14) 0.4850(3) 0.0285(7) Uani 1 1 d . . . O1 O 0.56647(9) 0.51431(12) 0.4852(2) 0.0589(7) Uani 1 1 d . . . C20 C 0.44588(12) 0.30895(14) 0.4964(3) 0.0311(7) Uani 1 1 d . . . H20A H 0.4480 0.3528 0.5258 0.037 Uiso 1 1 calc R . . C25 C 0.33632(12) 0.18166(15) 0.3805(3) 0.0319(7) Uani 1 1 d . . . C4 C 0.54872(11) 0.30851(14) 0.5117(3) 0.0305(7) Uani 1 1 d . . . C5 C 0.55359(11) 0.34582(16) 0.3796(3) 0.0346(7) Uani 1 1 d . . . H5A H 0.5540 0.3212 0.2989 0.042 Uiso 1 1 calc R . . C7 C 0.59465(12) 0.25894(14) 0.5477(3) 0.0303(7) Uani 1 1 d . . . C27 C 0.23959(13) 0.18843(17) 0.3167(3) 0.0453(8) Uani 1 1 d . . . H27A H 0.2086 0.2142 0.2987 0.054 Uiso 1 1 calc R . . C9 C 0.63763(12) 0.17341(15) 0.6994(3) 0.0362(8) Uani 1 1 d . . . H9A H 0.6370 0.1461 0.7761 0.043 Uiso 1 1 calc R . . C23 C 0.43768(13) 0.18058(16) 0.4020(3) 0.0420(8) Uani 1 1 d . . . H23A H 0.4356 0.1375 0.3678 0.050 Uiso 1 1 calc R . . C13 C 0.72811(12) 0.12540(14) 0.6687(3) 0.0328(7) Uani 1 1 d . . . C18 C 0.75905(12) 0.10083(15) 0.5718(3) 0.0373(8) Uani 1 1 d . . . H18A H 0.7489 0.1098 0.4779 0.045 Uiso 1 1 calc R . . C21 C 0.39607(12) 0.27935(15) 0.4647(3) 0.0326(7) Uani 1 1 d . . . H21A H 0.3654 0.3036 0.4754 0.039 Uiso 1 1 calc R . . C26 C 0.28905(13) 0.21846(16) 0.3532(3) 0.0391(8) Uani 1 1 d . . . H26A H 0.2908 0.2644 0.3597 0.047 Uiso 1 1 calc R . . C3 C 0.55133(11) 0.35598(16) 0.6329(3) 0.0346(7) Uani 1 1 d . . . H3A H 0.5490 0.3380 0.7199 0.042 Uiso 1 1 calc R . . C11 C 0.68004(12) 0.21103(15) 0.5101(3) 0.0361(8) Uani 1 1 d . . . H11A H 0.7080 0.2091 0.4568 0.043 Uiso 1 1 calc R . . C10 C 0.68133(11) 0.16958(14) 0.6249(3) 0.0309(7) Uani 1 1 d . . . C6 C 0.55735(12) 0.41146(16) 0.3704(3) 0.0382(8) Uani 1 1 d . . . H6A H 0.5582 0.4308 0.2839 0.046 Uiso 1 1 calc R . . C2 C 0.55672(11) 0.42098(16) 0.6250(3) 0.0382(8) Uani 1 1 d . . . H2A H 0.5584 0.4463 0.7054 0.046 Uiso 1 1 calc R . . C8 C 0.59579(12) 0.21646(14) 0.6620(3) 0.0350(7) Uani 1 1 d . . . H8A H 0.5674 0.2175 0.7139 0.042 Uiso 1 1 calc R . . C24 C 0.48789(13) 0.20942(15) 0.4363(3) 0.0409(8) Uani 1 1 d . . . H24A H 0.5187 0.1851 0.4267 0.049 Uiso 1 1 calc R . . C12 C 0.63817(12) 0.25498(15) 0.4736(3) 0.0330(7) Uani 1 1 d . . . H12A H 0.6390 0.2827 0.3975 0.040 Uiso 1 1 calc R . . C30 C 0.33120(13) 0.11291(16) 0.3716(3) 0.0413(8) Uani 1 1 d . . . H30A H 0.3619 0.0868 0.3910 0.050 Uiso 1 1 calc R . . C28 C 0.23585(14) 0.11986(17) 0.3068(3) 0.0422(8) Uani 1 1 d . . . H28A H 0.2026 0.0996 0.2814 0.051 Uiso 1 1 calc R . . C17 C 0.80471(13) 0.06323(15) 0.6138(3) 0.0431(8) Uani 1 1 d . . . H17A H 0.8247 0.0467 0.5479 0.052 Uiso 1 1 calc R . . C1 C 0.56010(12) 0.45367(17) 0.4930(3) 0.0428(8) Uani 1 1 d . . . C15 C 0.79043(13) 0.07330(16) 0.8495(3) 0.0438(8) Uani 1 1 d . . . H15A H 0.8007 0.0637 0.9432 0.053 Uiso 1 1 calc R . . C14 C 0.74470(13) 0.11064(15) 0.8089(3) 0.0386(8) Uani 1 1 d . . . H14A H 0.7247 0.1262 0.8757 0.046 Uiso 1 1 calc R . . C29 C 0.28181(14) 0.08250(17) 0.3348(3) 0.0465(9) Uani 1 1 d . . . H29A H 0.2797 0.0366 0.3291 0.056 Uiso 1 1 calc R . . C16 C 0.82087(13) 0.05016(16) 0.7535(3) 0.0452(8) Uani 1 1 d . . . H16A H 0.8521 0.0259 0.7818 0.054 Uiso 1 1 calc R . . C32 C 0.5746(3) 0.0105(3) 0.8331(6) 0.141(3) Uani 1 1 d . . . C33 C 0.5232(5) 0.0457(8) 0.7899(11) 0.167(6) Uani 0.55 1 d P . 1 H33A H 0.5115 0.0524 0.8797 0.251 Uiso 0.55 1 calc PR . 1 H33B H 0.5368 0.0886 0.7667 0.251 Uiso 0.55 1 calc PR . 1 C34 C 0.5114(4) -0.0176(6) 0.7913(10) 0.078(3) Uani 0.45 1 d P . 2 H34A H 0.5133 -0.0637 0.8197 0.117 Uiso 0.45 1 calc PR . 2 H34B H 0.4912 0.0047 0.8557 0.117 Uiso 0.45 1 calc PR . 2 C31 C 0.5970(2) -0.0431(3) 0.9194(5) 0.122(2) Uani 1 1 d . . 2 H31D H 0.6342 -0.0340 0.9526 0.183 Uiso 1 1 calc R . 2 H31E H 0.5942 -0.0834 0.8665 0.183 Uiso 1 1 calc R . 2 H31F H 0.5775 -0.0477 0.9970 0.183 Uiso 1 1 calc R . 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C22 0.0345(19) 0.0325(18) 0.0276(14) -0.0002(12) 0.0071(12) -0.0003(15) C19 0.0338(18) 0.0273(17) 0.0255(13) 0.0007(12) 0.0075(12) 0.0005(14) O1 0.0500(16) 0.0370(15) 0.0866(17) 0.0029(12) -0.0004(12) -0.0066(12) C20 0.0374(19) 0.0292(17) 0.0270(14) -0.0029(12) 0.0057(12) -0.0042(16) C25 0.0376(19) 0.0336(18) 0.0253(14) 0.0010(12) 0.0070(12) -0.0013(16) C4 0.0319(18) 0.0317(17) 0.0280(14) -0.0011(12) 0.0047(12) 0.0024(15) C5 0.0257(17) 0.048(2) 0.0293(14) 0.0029(13) 0.0024(12) -0.0023(15) C7 0.0324(18) 0.0323(17) 0.0263(13) -0.0012(12) 0.0044(12) -0.0035(14) C27 0.038(2) 0.056(2) 0.0412(17) 0.0084(16) 0.0033(14) 0.0003(19) C9 0.041(2) 0.0359(18) 0.0330(15) 0.0047(13) 0.0097(13) -0.0001(16) C23 0.042(2) 0.0325(19) 0.0517(19) -0.0132(15) 0.0068(15) -0.0013(17) C13 0.0354(18) 0.0280(17) 0.0355(15) -0.0037(13) 0.0072(13) -0.0080(15) C18 0.0381(19) 0.0412(19) 0.0327(15) -0.0037(13) 0.0059(13) -0.0036(17) C21 0.0324(19) 0.0346(18) 0.0314(14) 0.0014(13) 0.0066(12) 0.0033(15) C26 0.040(2) 0.0371(19) 0.0396(16) 0.0036(14) 0.0054(14) 0.0003(17) C3 0.0299(18) 0.043(2) 0.0312(14) -0.0033(13) 0.0045(12) -0.0002(16) C11 0.0364(19) 0.045(2) 0.0276(14) -0.0019(13) 0.0075(13) 0.0015(17) C10 0.0325(18) 0.0341(18) 0.0255(14) -0.0043(12) 0.0024(12) -0.0028(15) C6 0.0307(19) 0.040(2) 0.0434(17) 0.0124(14) 0.0027(13) -0.0023(15) C2 0.0296(19) 0.037(2) 0.0474(17) -0.0110(15) 0.0023(14) -0.0010(16) C8 0.0341(18) 0.0384(19) 0.0347(15) 0.0005(13) 0.0127(13) 0.0003(16) C24 0.036(2) 0.037(2) 0.0494(18) -0.0080(14) 0.0043(14) 0.0039(17) C12 0.0352(19) 0.0374(18) 0.0260(13) 0.0036(13) 0.0037(12) -0.0015(16) C30 0.037(2) 0.039(2) 0.0491(18) -0.0020(14) 0.0076(14) -0.0034(17) C28 0.046(2) 0.049(2) 0.0302(15) 0.0008(14) 0.0033(13) -0.0165(18) C17 0.034(2) 0.038(2) 0.059(2) -0.0067(16) 0.0153(15) -0.0022(17) C1 0.0287(19) 0.035(2) 0.062(2) 0.0023(16) -0.0014(15) -0.0016(16) C15 0.047(2) 0.041(2) 0.0423(17) 0.0030(15) 0.0017(15) 0.0005(18) C14 0.047(2) 0.0327(18) 0.0362(15) -0.0006(13) 0.0076(14) 0.0073(17) C29 0.047(2) 0.042(2) 0.0509(19) -0.0031(15) 0.0091(16) -0.0063(19) C16 0.034(2) 0.039(2) 0.061(2) 0.0009(16) 0.0036(16) -0.0025(17) C32 0.189(7) 0.124(5) 0.096(4) 0.021(4) -0.022(4) 0.032(5) C33 0.138(13) 0.279(18) 0.083(8) 0.021(10) 0.011(7) -0.102(13) C34 0.059(9) 0.101(8) 0.073(9) -0.003(6) 0.007(6) 0.002(7) C31 0.159(6) 0.108(5) 0.100(4) -0.008(3) 0.018(4) -0.006(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C22 C23 1.395(4) . ? C22 C21 1.400(4) . ? C22 C25 1.493(4) . ? C19 C24 1.390(4) . ? C19 C20 1.394(4) . ? C19 C4 1.544(4) . ? O1 C1 1.238(4) . ? C20 C21 1.378(4) . ? C25 C26 1.391(4) . ? C25 C30 1.395(4) . ? C4 C5 1.508(4) . ? C4 C3 1.513(4) . ? C4 C7 1.527(4) . ? C5 C6 1.332(4) . ? C7 C12 1.393(4) . ? C7 C8 1.401(4) . ? C27 C26 1.379(4) . ? C27 C28 1.390(4) . ? C9 C8 1.370(4) . ? C9 C10 1.399(4) . ? C23 C24 1.383(4) . ? C13 C18 1.394(4) . ? C13 C14 1.399(4) . ? C13 C10 1.486(4) . ? C18 C17 1.385(4) . ? C3 C2 1.322(4) . ? C11 C12 1.381(4) . ? C11 C10 1.392(4) . ? C6 C1 1.459(4) . ? C2 C1 1.457(4) . ? C30 C29 1.382(4) . ? C28 C29 1.371(4) . ? C17 C16 1.385(4) . ? C15 C16 1.370(4) . ? C15 C14 1.381(4) . ? C32 C31 1.432(7) . ? C32 C33 1.477(14) . ? C32 C34 1.675(13) . ? C33 C33 1.30(2) 2_656 ? C34 C34 0.916(16) 2_656 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C23 C22 C21 116.0(3) . . ? C23 C22 C25 121.3(3) . . ? C21 C22 C25 122.7(3) . . ? C24 C19 C20 117.5(3) . . ? C24 C19 C4 121.2(3) . . ? C20 C19 C4 121.1(2) . . ? C21 C20 C19 121.1(3) . . ? C26 C25 C30 116.8(3) . . ? C26 C25 C22 121.8(3) . . ? C30 C25 C22 121.4(3) . . ? C5 C4 C3 110.3(2) . . ? C5 C4 C7 111.8(2) . . ? C3 C4 C7 106.8(2) . . ? C5 C4 C19 105.2(2) . . ? C3 C4 C19 110.6(2) . . ? C7 C4 C19 112.1(2) . . ? C6 C5 C4 124.7(3) . . ? C12 C7 C8 116.6(3) . . ? C12 C7 C4 122.6(2) . . ? C8 C7 C4 120.8(2) . . ? C26 C27 C28 120.3(3) . . ? C8 C9 C10 121.6(3) . . ? C24 C23 C22 122.2(3) . . ? C18 C13 C14 117.8(3) . . ? C18 C13 C10 120.8(2) . . ? C14 C13 C10 121.2(3) . . ? C17 C18 C13 120.8(3) . . ? C20 C21 C22 122.2(3) . . ? C27 C26 C25 121.5(3) . . ? C2 C3 C4 125.2(3) . . ? C12 C11 C10 121.4(3) . . ? C11 C10 C9 116.9(3) . . ? C11 C10 C13 121.1(3) . . ? C9 C10 C13 121.9(2) . . ? C5 C6 C1 121.4(3) . . ? C3 C2 C1 121.3(3) . . ? C9 C8 C7 121.8(3) . . ? C23 C24 C19 121.1(3) . . ? C11 C12 C7 121.8(3) . . ? C29 C30 C25 121.9(3) . . ? C29 C28 C27 119.2(3) . . ? C18 C17 C16 120.4(3) . . ? O1 C1 C2 121.7(3) . . ? O1 C1 C6 121.3(3) . . ? C2 C1 C6 117.0(3) . . ? C16 C15 C14 120.8(3) . . ? C15 C14 C13 120.9(3) . . ? C28 C29 C30 120.2(3) . . ? C15 C16 C17 119.4(3) . . ? C31 C32 C33 141.4(8) . . ? C31 C32 C34 99.4(7) . . ? C33 C32 C34 48.7(6) . . ? C33 C33 C32 146.8(10) 2_656 . ? C34 C34 C32 131.4(18) 2_656 . ? _diffrn_measured_fraction_theta_max 0.946 _diffrn_reflns_theta_full 26.41 _diffrn_measured_fraction_theta_full 0.946 _refine_diff_density_max 0.344 _refine_diff_density_min -0.295 _refine_diff_density_rms 0.066