Electronic Supplementary Material for CrystEngComm This Journal is © The Royal Society of Chemistry 2003 data_global _publ_contact_author_email desiraju@uohyd.ernet.in _publ_contact_author_name 'Prof. Gautam R. Desiraju' _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_address ; School of Chemistry University of Hyderabad Hyderabad - 500 046 India ; _publ_contact_author_phone '91 40 23010500 extn. 4828' _publ_contact_author_fax '91 40 23010567' _publ_section_title ; Multiple molecules in the crystallographic asymmetric unit. Self host-guest and doubly interpenetrated hydrogen bond networks in a pair of keto-bisphenols. ; loop_ _publ_author_name _publ_author_address S.Aitipamula ;School of Chemistry University of Hyderabad Hyderabad - 500 046 India ; G.R.Desiraju ;School of Chemistry University of Hyderabad Hyderabad - 500 046 India ; M.Jaskolski ;Center for Biocrystallographic Research IBCh, Polish Academy of Sciences and Department of Crystallography Faculty of Chemistry A. Mickiewicz University Grunwaldzka 6, 60-780 Poznan Poland ; A.Nangia ;School of Chemistry University of Hyderabad Hyderabad - 500 046 India ; R.Thaimattam ;Center for Biocrystallographic Research IBCh, Polish Academy of Sciences and Department of Crystallography Faculty of Chemistry A. Mickiewicz University Grunwaldzka 6, 60-780 Poznan Poland ; data_compound_1 _database_code_CSD 211016 _chemical_name_common 4,4-bis(4-hydroxyphenyl)cyclohexanone _audit_creation_method SHELXL-97 _chemical_name_systematic 4,4-bis(4-hydroxyphenyl)cyclohexanone _chemical_melting_point 508 _chemical_formula_moiety 'C18 H18 O3' _chemical_formula_sum 'C18 H18 O3' _chemical_formula_weight 282.32 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 Cc _symmetry_Int_Tables_number 9 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' 'x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z+1/2' _cell_length_a 14.391(3) _cell_length_b 20.228(4) _cell_length_c 9.782(2) _cell_angle_alpha 90.00 _cell_angle_beta 91.96(3) _cell_angle_gamma 90.00 _cell_volume 2845.9(10) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1245 _cell_measurement_theta_min 3.34 _cell_measurement_theta_max 27.49 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.318 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1200 _exptl_absorpt_coefficient_mu 0.089 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(1) _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_probe ? _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'KUMA CCD' _diffrn_measurement_method 'oscillation method' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12728 _diffrn_reflns_av_R_equivalents 0.0364 _diffrn_reflns_av_sigmaI/netI 0.0389 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.34 _diffrn_reflns_theta_max 27.49 _reflns_number_total 4288 _reflns_number_gt 4029 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'KUMA CCD' _computing_cell_refinement 'KUMA CCD' _computing_data_reduction 'KUMA CrysAlis' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics XP _computing_publication_material SHELX-97 _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^)+(0.0448P)^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 0.0029(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4288 _refine_ls_number_parameters 396 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0421 _refine_ls_R_factor_gt 0.0373 _refine_ls_wR_factor_ref 0.0779 _refine_ls_wR_factor_gt 0.0760 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_restrained_S_all 1.054 _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 O1 O 0.55063(10) 0.19115(7) 0.33879(15) 0.0216(3) Uani 1 1 d . . . O2 O 0.05099(10) 0.26869(7) 0.57016(16) 0.0188(3) Uani 1 1 d . . . O3 O 0.16922(12) -0.18678(7) 0.49969(15) 0.0199(3) Uani 1 1 d . . . O1A O 0.36645(11) 0.29417(7) 1.37785(15) 0.0227(3) Uani 1 1 d . . . O2A O 0.04726(10) 0.62749(7) 0.87838(16) 0.0220(3) Uani 1 1 d . . . O3A O 0.48549(11) 0.33038(7) 0.57725(15) 0.0211(3) Uani 1 1 d . . . C1 C 0.48038(14) 0.16198(10) 0.3709(2) 0.0166(4) Uani 1 1 d . . . C2 C 0.46029(15) 0.14791(10) 0.5185(2) 0.0168(4) Uani 1 1 d . . . H2B H 0.4208 0.1827 0.5525 0.020 Uiso 1 1 calc R . . H2C H 0.5183 0.1488 0.5721 0.020 Uiso 1 1 calc R . . C3 C 0.41241(14) 0.08082(9) 0.5395(2) 0.0141(4) Uani 1 1 d . . . H3B H 0.3956 0.0768 0.6343 0.017 Uiso 1 1 calc R . . H3C H 0.4557 0.0455 0.5201 0.017 Uiso 1 1 calc R . . C4 C 0.32396(14) 0.07301(9) 0.44600(19) 0.0128(4) Uani 1 1 d . . . C5 C 0.35671(14) 0.07741(10) 0.29723(19) 0.0142(4) Uani 1 1 d . . . H5A H 0.3979 0.0406 0.2805 0.017 Uiso 1 1 calc R . . H5B H 0.3030 0.0731 0.2351 0.017 Uiso 1 1 calc R . . C6 C 0.40735(15) 0.14192(10) 0.2651(2) 0.0174(4) Uani 1 1 d . . . H6A H 0.4365 0.1372 0.1777 0.021 Uiso 1 1 calc R . . H6B H 0.3618 0.1771 0.2559 0.021 Uiso 1 1 calc R . . C7 C 0.25221(14) 0.12666(9) 0.4781(2) 0.0141(4) Uani 1 1 d . . . C8 C 0.23645(15) 0.14459(10) 0.6133(2) 0.0170(4) Uani 1 1 d . . . H8A H 0.2715 0.1245 0.6833 0.020 Uiso 1 1 calc R . . C9 C 0.17043(15) 0.19129(10) 0.6471(2) 0.0177(4) Uani 1 1 d . . . H9A H 0.1617 0.2023 0.7380 0.021 Uiso 1 1 calc R . . C10 C 0.11732(13) 0.22145(9) 0.5428(2) 0.0154(4) Uani 1 1 d . . . C11 C 0.12978(15) 0.20386(10) 0.4087(2) 0.0171(4) Uani 1 1 d . . . H11A H 0.0934 0.2233 0.3394 0.021 Uiso 1 1 calc R . . C12 C 0.19611(14) 0.15739(10) 0.3764(2) 0.0154(4) Uani 1 1 d . . . H12A H 0.2037 0.1462 0.2853 0.018 Uiso 1 1 calc R . . C13 C 0.28108(14) 0.00353(9) 0.46345(19) 0.0140(4) Uani 1 1 d . . . C14 C 0.18704(14) -0.00499(10) 0.4873(2) 0.0166(4) Uani 1 1 d . . . H14A H 0.1493 0.0320 0.4961 0.020 Uiso 1 1 calc R . . C15 C 0.14804(15) -0.06807(10) 0.4982(2) 0.0176(4) Uani 1 1 d . . . H15A H 0.0850 -0.0725 0.5137 0.021 Uiso 1 1 calc R . . C16 C 0.20278(14) -0.12369(10) 0.48610(19) 0.0152(4) Uani 1 1 d . . . C17 C 0.29716(15) -0.11636(10) 0.45902(19) 0.0165(4) Uani 1 1 d . . . H17A H 0.3345 -0.1534 0.4487 0.020 Uiso 1 1 calc R . . C18 C 0.33454(15) -0.05351(9) 0.4476(2) 0.0153(4) Uani 1 1 d . . . H18A H 0.3972 -0.0491 0.4289 0.018 Uiso 1 1 calc R . . C1A C 0.35588(15) 0.32304(10) 1.2683(2) 0.0182(4) Uani 1 1 d . . . C2A C 0.41748(15) 0.37823(10) 1.2249(2) 0.0185(4) Uani 1 1 d . . . H2AB H 0.4585 0.3623 1.1554 0.022 Uiso 1 1 calc R . . H2AC H 0.4557 0.3930 1.3026 0.022 Uiso 1 1 calc R . . C3A C 0.35983(15) 0.43669(10) 1.1676(2) 0.0164(4) Uani 1 1 d . . . H3AB H 0.4018 0.4705 1.1358 0.020 Uiso 1 1 calc R . . H3AC H 0.3245 0.4556 1.2406 0.020 Uiso 1 1 calc R . . C4A C 0.29220(14) 0.41686(10) 1.04872(19) 0.0149(4) Uani 1 1 d . . . C5A C 0.22758(14) 0.36350(10) 1.1066(2) 0.0158(4) Uani 1 1 d . . . H5AA H 0.1908 0.3833 1.1772 0.019 Uiso 1 1 calc R . . H5AB H 0.1851 0.3485 1.0340 0.019 Uiso 1 1 calc R . . C6A C 0.27987(15) 0.30340(10) 1.1672(2) 0.0193(4) Uani 1 1 d . . . H6AA H 0.2361 0.2749 1.2121 0.023 Uiso 1 1 calc R . . H6AB H 0.3066 0.2784 1.0936 0.023 Uiso 1 1 calc R . . C7A C 0.23108(14) 0.47596(10) 1.0020(2) 0.0156(4) Uani 1 1 d . . . C8A C 0.23764(15) 0.53853(10) 1.0616(2) 0.0180(4) Uani 1 1 d . . . H8AA H 0.2830 0.5463 1.1296 0.022 Uiso 1 1 calc R . . C9A C 0.17775(15) 0.58968(10) 1.0216(2) 0.0196(5) Uani 1 1 d . . . H9AA H 0.1835 0.6309 1.0631 0.024 Uiso 1 1 calc R . . C10A C 0.10995(14) 0.57935(10) 0.9206(2) 0.0178(4) Uani 1 1 d . . . C11A C 0.10398(14) 0.51813(10) 0.8557(2) 0.0182(4) Uani 1 1 d . . . H11B H 0.0601 0.5112 0.7851 0.022 Uiso 1 1 calc R . . C12A C 0.16382(14) 0.46759(10) 0.8969(2) 0.0165(4) Uani 1 1 d . . . H12B H 0.1590 0.4268 0.8532 0.020 Uiso 1 1 calc R . . C13A C 0.34451(13) 0.39122(9) 0.92476(19) 0.0140(4) Uani 1 1 d . . . C14A C 0.42634(14) 0.42200(10) 0.8840(2) 0.0165(4) Uani 1 1 d . . . H14B H 0.4503 0.4571 0.9356 0.020 Uiso 1 1 calc R . . C15A C 0.47254(14) 0.40187(10) 0.7695(2) 0.0172(4) Uani 1 1 d . . . H15B H 0.5269 0.4231 0.7454 0.021 Uiso 1 1 calc R . . C16A C 0.43770(14) 0.35000(10) 0.6907(2) 0.0166(4) Uani 1 1 d . . . C17A C 0.35682(14) 0.31841(10) 0.7276(2) 0.0173(4) Uani 1 1 d . . . H17B H 0.3331 0.2836 0.6751 0.021 Uiso 1 1 calc R . . C18A C 0.31122(14) 0.33885(10) 0.8431(2) 0.0171(4) Uani 1 1 d . . . H18C H 0.2571 0.3172 0.8669 0.020 Uiso 1 1 calc R . . H2A H 0.055(2) 0.2806(14) 0.658(3) 0.039(8) Uiso 1 1 d . . . H3AA H 0.4488(17) 0.3175(11) 0.513(3) 0.023(6) Uiso 1 1 d . . . H2AA H 0.051(2) 0.6627(16) 0.938(3) 0.057(9) Uiso 1 1 d . . . H3A H 0.112(3) -0.1860(16) 0.518(3) 0.055(10) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0174(8) 0.0234(8) 0.0239(8) 0.0036(6) 0.0018(6) -0.0058(6) O2 0.0171(8) 0.0179(7) 0.0215(8) -0.0024(6) 0.0025(6) 0.0049(6) O3 0.0200(9) 0.0154(7) 0.0243(8) 0.0015(6) 0.0017(7) -0.0035(6) O1A 0.0290(9) 0.0199(8) 0.0191(8) 0.0023(6) -0.0039(6) -0.0012(6) O2A 0.0206(8) 0.0180(7) 0.0271(8) 0.0004(6) -0.0034(7) 0.0040(6) O3A 0.0174(8) 0.0283(8) 0.0176(8) -0.0050(6) 0.0020(6) -0.0019(7) C1 0.0143(10) 0.0138(10) 0.0217(10) -0.0001(8) 0.0013(8) 0.0020(8) C2 0.0157(10) 0.0194(10) 0.0153(10) -0.0016(8) 0.0000(8) -0.0021(8) C3 0.0122(10) 0.0165(9) 0.0138(9) 0.0002(8) 0.0018(8) 0.0009(8) C4 0.0130(10) 0.0141(9) 0.0113(9) -0.0005(8) 0.0027(7) 0.0001(8) C5 0.0140(10) 0.0155(9) 0.0131(10) -0.0007(7) 0.0018(8) 0.0014(8) C6 0.0158(10) 0.0210(10) 0.0156(10) 0.0013(8) 0.0021(8) -0.0018(8) C7 0.0145(10) 0.0127(9) 0.0151(9) 0.0003(7) 0.0021(8) -0.0024(8) C8 0.0180(11) 0.0200(10) 0.0130(10) 0.0004(8) -0.0006(8) 0.0009(8) C9 0.0190(11) 0.0206(10) 0.0136(10) -0.0025(8) 0.0037(8) -0.0010(8) C10 0.0122(10) 0.0119(9) 0.0222(11) -0.0012(8) 0.0030(8) 0.0006(8) C11 0.0154(10) 0.0176(10) 0.0182(10) 0.0016(8) -0.0019(8) 0.0003(8) C12 0.0166(10) 0.0159(10) 0.0136(9) -0.0021(7) 0.0004(8) -0.0011(8) C13 0.0163(10) 0.0139(9) 0.0117(10) 0.0007(7) -0.0009(8) -0.0016(8) C14 0.0169(11) 0.0155(10) 0.0175(10) 0.0014(8) 0.0026(8) 0.0016(8) C15 0.0153(11) 0.0218(10) 0.0157(10) 0.0028(8) 0.0014(8) -0.0025(8) C16 0.0192(11) 0.0159(10) 0.0105(9) 0.0009(7) -0.0006(8) -0.0035(8) C17 0.0193(11) 0.0153(9) 0.0149(10) -0.0006(8) -0.0004(8) 0.0040(8) C18 0.0135(10) 0.0203(10) 0.0120(9) 0.0016(8) -0.0014(8) -0.0002(8) C1A 0.0204(11) 0.0143(9) 0.0199(11) -0.0040(8) -0.0005(9) 0.0038(8) C2A 0.0160(10) 0.0204(10) 0.0188(11) -0.0017(8) -0.0031(8) -0.0011(8) C3A 0.0163(10) 0.0176(10) 0.0153(10) -0.0016(8) -0.0007(8) -0.0013(8) C4A 0.0136(10) 0.0148(10) 0.0164(10) -0.0014(7) -0.0002(8) -0.0001(8) C5A 0.0140(10) 0.0178(10) 0.0158(10) 0.0004(8) 0.0017(8) -0.0010(8) C6A 0.0212(11) 0.0166(10) 0.0198(11) 0.0007(8) -0.0020(8) -0.0046(9) C7A 0.0123(10) 0.0186(10) 0.0161(10) 0.0018(8) 0.0040(8) -0.0014(8) C8A 0.0162(10) 0.0194(10) 0.0184(10) -0.0013(8) -0.0019(8) -0.0024(8) C9A 0.0217(11) 0.0147(10) 0.0226(11) -0.0037(8) 0.0014(9) -0.0011(8) C10A 0.0151(11) 0.0179(10) 0.0207(11) 0.0048(8) 0.0037(8) -0.0005(8) C11A 0.0131(10) 0.0224(11) 0.0188(10) 0.0004(8) -0.0011(8) -0.0036(8) C12A 0.0178(10) 0.0144(10) 0.0175(10) -0.0025(8) 0.0031(8) -0.0033(8) C13A 0.0117(10) 0.0156(9) 0.0145(10) 0.0003(7) -0.0003(8) 0.0030(8) C14A 0.0158(10) 0.0153(10) 0.0182(10) -0.0007(8) -0.0029(8) -0.0008(8) C15A 0.0118(10) 0.0195(10) 0.0201(11) 0.0041(8) -0.0007(8) -0.0030(8) C16A 0.0147(10) 0.0191(10) 0.0161(10) 0.0010(8) 0.0006(8) 0.0039(8) C17A 0.0170(11) 0.0148(9) 0.0199(11) -0.0033(8) -0.0020(9) -0.0007(8) C18A 0.0125(10) 0.0177(10) 0.0210(11) 0.0002(8) 0.0012(8) -0.0044(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.221(3) . ? O2 C10 1.383(2) . ? O2 H2A 0.90(3) . ? O3 C16 1.373(2) . ? O3 H3A 0.85(4) . ? O1A C1A 1.225(2) . ? O2A C10A 1.381(2) . ? O2A H2AA 0.92(3) . ? O3A C16A 1.384(3) . ? O3A H3AA 0.85(2) . ? C1 C6 1.505(3) . ? C1 C2 1.510(3) . ? C2 C3 1.539(3) . ? C2 H2B 0.9700 . ? C2 H2C 0.9700 . ? C3 C4 1.550(3) . ? C3 H3B 0.9700 . ? C3 H3C 0.9700 . ? C4 C7 1.538(3) . ? C4 C13 1.547(3) . ? C4 C5 1.548(3) . ? C5 C6 1.532(3) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.398(3) . ? C7 C12 1.404(3) . ? C8 C9 1.388(3) . ? C8 H8A 0.9300 . ? C9 C10 1.394(3) . ? C9 H9A 0.9300 . ? C10 C11 1.376(3) . ? C11 C12 1.384(3) . ? C11 H11A 0.9300 . ? C12 H12A 0.9300 . ? C13 C14 1.392(3) . ? C13 C18 1.398(3) . ? C14 C15 1.399(3) . ? C14 H14A 0.9300 . ? C15 C16 1.381(3) . ? C15 H15A 0.9300 . ? C16 C17 1.401(3) . ? C17 C18 1.386(3) . ? C17 H17A 0.9300 . ? C18 H18A 0.9300 . ? C1A C2A 1.496(3) . ? C1A C6A 1.503(3) . ? C2A C3A 1.539(3) . ? C2A H2AB 0.9700 . ? C2A H2AC 0.9700 . ? C3A C4A 1.544(3) . ? C3A H3AB 0.9700 . ? C3A H3AC 0.9700 . ? C4A C13A 1.539(3) . ? C4A C7A 1.544(3) . ? C4A C5A 1.545(3) . ? C5A C6A 1.538(3) . ? C5A H5AA 0.9700 . ? C5A H5AB 0.9700 . ? C6A H6AA 0.9700 . ? C6A H6AB 0.9700 . ? C7A C8A 1.395(3) . ? C7A C12A 1.398(3) . ? C8A C9A 1.394(3) . ? C8A H8AA 0.9300 . ? C9A C10A 1.380(3) . ? C9A H9AA 0.9300 . ? C10A C11A 1.393(3) . ? C11A C12A 1.388(3) . ? C11A H11B 0.9300 . ? C12A H12B 0.9300 . ? C13A C18A 1.401(3) . ? C13A C14A 1.402(3) . ? C14A C15A 1.383(3) . ? C14A H14B 0.9300 . ? C15A C16A 1.385(3) . ? C15A H15B 0.9300 . ? C16A C17A 1.386(3) . ? C17A C18A 1.389(3) . ? C17A H17B 0.9300 . ? C18A H18C 0.9300 . ? 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 C10 O2 H2A 110.2(19) . . ? C16 O3 H3A 111(2) . . ? C10A O2A H2AA 109.6(19) . . ? C16A O3A H3AA 111.5(17) . . ? O1 C1 C6 121.24(18) . . ? O1 C1 C2 121.62(18) . . ? C6 C1 C2 117.05(17) . . ? C1 C2 C3 113.27(16) . . ? C1 C2 H2B 108.9 . . ? C3 C2 H2B 108.9 . . ? C1 C2 H2C 108.9 . . ? C3 C2 H2C 108.9 . . ? H2B C2 H2C 107.7 . . ? C2 C3 C4 111.94(15) . . ? C2 C3 H3B 109.2 . . ? C4 C3 H3B 109.2 . . ? C2 C3 H3C 109.2 . . ? C4 C3 H3C 109.2 . . ? H3B C3 H3C 107.9 . . ? C7 C4 C13 110.22(16) . . ? C7 C4 C5 112.30(15) . . ? C13 C4 C5 106.95(15) . . ? C7 C4 C3 110.56(15) . . ? C13 C4 C3 110.50(15) . . ? C5 C4 C3 106.18(15) . . ? C6 C5 C4 113.83(16) . . ? C6 C5 H5A 108.8 . . ? C4 C5 H5A 108.8 . . ? C6 C5 H5B 108.8 . . ? C4 C5 H5B 108.8 . . ? H5A C5 H5B 107.7 . . ? C1 C6 C5 114.48(17) . . ? C1 C6 H6A 108.6 . . ? C5 C6 H6A 108.6 . . ? C1 C6 H6B 108.6 . . ? C5 C6 H6B 108.6 . . ? H6A C6 H6B 107.6 . . ? C8 C7 C12 116.57(18) . . ? C8 C7 C4 120.53(17) . . ? C12 C7 C4 122.81(17) . . ? C9 C8 C7 122.43(18) . . ? C9 C8 H8A 118.8 . . ? C7 C8 H8A 118.8 . . ? C8 C9 C10 119.11(18) . . ? C8 C9 H9A 120.4 . . ? C10 C9 H9A 120.4 . . ? C11 C10 O2 118.45(17) . . ? C11 C10 C9 119.87(18) . . ? O2 C10 C9 121.68(18) . . ? C10 C11 C12 120.43(18) . . ? C10 C11 H11A 119.8 . . ? C12 C11 H11A 119.8 . . ? C11 C12 C7 121.57(18) . . ? C11 C12 H12A 119.2 . . ? C7 C12 H12A 119.2 . . ? C14 C13 C18 117.26(17) . . ? C14 C13 C4 121.67(17) . . ? C18 C13 C4 120.96(17) . . ? C13 C14 C15 121.37(19) . . ? C13 C14 H14A 119.3 . . ? C15 C14 H14A 119.3 . . ? C16 C15 C14 120.32(19) . . ? C16 C15 H15A 119.8 . . ? C14 C15 H15A 119.8 . . ? O3 C16 C15 123.07(18) . . ? O3 C16 C17 117.61(18) . . ? C15 C16 C17 119.32(18) . . ? C18 C17 C16 119.58(19) . . ? C18 C17 H17A 120.2 . . ? C16 C17 H17A 120.2 . . ? C17 C18 C13 122.10(19) . . ? C17 C18 H18A 119.0 . . ? C13 C18 H18A 119.0 . . ? O1A C1A C2A 123.18(18) . . ? O1A C1A C6A 121.02(19) . . ? C2A C1A C6A 115.78(17) . . ? C1A C2A C3A 111.07(17) . . ? C1A C2A H2AB 109.4 . . ? C3A C2A H2AB 109.4 . . ? C1A C2A H2AC 109.4 . . ? C3A C2A H2AC 109.4 . . ? H2AB C2A H2AC 108.0 . . ? C2A C3A C4A 113.13(16) . . ? C2A C3A H3AB 109.0 . . ? C4A C3A H3AB 109.0 . . ? C2A C3A H3AC 109.0 . . ? C4A C3A H3AC 109.0 . . ? H3AB C3A H3AC 107.8 . . ? C13A C4A C3A 111.60(16) . . ? C13A C4A C7A 108.47(15) . . ? C3A C4A C7A 111.10(15) . . ? C13A C4A C5A 111.72(16) . . ? C3A C4A C5A 106.11(15) . . ? C7A C4A C5A 107.79(16) . . ? C6A C5A C4A 113.64(17) . . ? C6A C5A H5AA 108.8 . . ? C4A C5A H5AA 108.8 . . ? C6A C5A H5AB 108.8 . . ? C4A C5A H5AB 108.8 . . ? H5AA C5A H5AB 107.7 . . ? C1A C6A C5A 112.34(16) . . ? C1A C6A H6AA 109.1 . . ? C5A C6A H6AA 109.1 . . ? C1A C6A H6AB 109.1 . . ? C5A C6A H6AB 109.1 . . ? H6AA C6A H6AB 107.9 . . ? C8A C7A C12A 116.90(18) . . ? C8A C7A C4A 123.28(17) . . ? C12A C7A C4A 119.81(17) . . ? C9A C8A C7A 121.57(19) . . ? C9A C8A H8AA 119.2 . . ? C7A C8A H8AA 119.2 . . ? C10A C9A C8A 120.23(18) . . ? C10A C9A H9AA 119.9 . . ? C8A C9A H9AA 119.9 . . ? C9A C10A O2A 123.08(18) . . ? C9A C10A C11A 119.47(19) . . ? O2A C10A C11A 117.44(18) . . ? C12A C11A C10A 119.64(19) . . ? C12A C11A H11B 120.2 . . ? C10A C11A H11B 120.2 . . ? C11A C12A C7A 122.11(18) . . ? C11A C12A H12B 118.9 . . ? C7A C12A H12B 118.9 . . ? C18A C13A C14A 116.60(18) . . ? C18A C13A C4A 122.49(18) . . ? C14A C13A C4A 120.83(17) . . ? C15A C14A C13A 122.08(18) . . ? C15A C14A H14B 119.0 . . ? C13A C14A H14B 119.0 . . ? C14A C15A C16A 119.90(19) . . ? C14A C15A H15B 120.0 . . ? C16A C15A H15B 120.0 . . ? O3A C16A C15A 118.88(18) . . ? O3A C16A C17A 121.43(18) . . ? C15A C16A C17A 119.69(19) . . ? C16A C17A C18A 119.93(18) . . ? C16A C17A H17B 120.0 . . ? C18A C17A H17B 120.0 . . ? C17A C18A C13A 121.81(18) . . ? C17A C18A H18C 119.1 . . ? C13A C18A H18C 119.1 . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.221 _refine_diff_density_min -0.163 _refine_diff_density_rms 0.038 #============== END data_compound_2 _database_code_CSD 211017 _chemical_name_common 4,4-bis(3-methyl-4-hydroxyphenyl)cyclohexanone _audit_creation_method SHELXL-97 _chemical_name_systematic 4,4-bis(3-methyl-4-hydroxyphenyl)cyclohexanone _chemical_melting_point 480 _chemical_formula_moiety 'C20 H22 O3' _chemical_formula_sum 'C20 H22 O3' _chemical_formula_weight 310.38 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' 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 _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 10.004(2) _cell_length_b 15.783(3) _cell_length_c 20.253(4) _cell_angle_alpha 90.00 _cell_angle_beta 94.79(3) _cell_angle_gamma 90.00 _cell_volume 3186.7(11) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 3.29 _cell_measurement_theta_max 27.50 _exptl_crystal_description needles _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.294 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1328 _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(1) _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_probe ? _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'KUMA CCD' _diffrn_measurement_method 'oscillation method' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 29031 _diffrn_reflns_av_R_equivalents 0.0558 _diffrn_reflns_av_sigmaI/netI 0.0694 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 3.29 _diffrn_reflns_theta_max 27.50 _reflns_number_total 7270 _reflns_number_gt 5516 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'KUMA CCD' _computing_cell_refinement 'KUMA CCD' _computing_data_reduction 'KUMA CrysAlis' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics XP _computing_publication_material SHELX-97 _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^)+(0.0463P)^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 0.0018(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 7270 _refine_ls_number_parameters 432 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1081 _refine_ls_R_factor_gt 0.0697 _refine_ls_wR_factor_ref 0.1263 _refine_ls_wR_factor_gt 0.1138 _refine_ls_goodness_of_fit_ref 1.165 _refine_ls_restrained_S_all 1.165 _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 O1 O 1.00238(15) 1.21744(9) 0.32639(7) 0.0219(4) Uani 1 1 d . . . O2 O 1.12437(16) 0.72026(9) 0.57113(7) 0.0203(4) Uani 1 1 d . . . O3 O 0.88704(18) 0.76669(10) 0.12497(7) 0.0232(4) Uani 1 1 d . . . O1A O 1.33462(15) 0.62432(9) 0.46358(7) 0.0227(4) Uani 1 1 d . . . O2A O 0.98517(16) 0.36346(10) 0.08877(7) 0.0229(4) Uani 1 1 d . . . O3A O 0.51717(16) 0.68869(10) 0.38252(8) 0.0238(4) Uani 1 1 d . . . C1 C 0.9889(2) 1.14052(13) 0.31789(10) 0.0177(5) Uani 1 1 d . . . C2 C 1.1012(2) 1.08642(13) 0.29757(10) 0.0196(5) Uani 1 1 d . . . H2B H 1.1796 1.1212 0.2925 0.023 Uiso 1 1 calc R . . H2C H 1.0751 1.0595 0.2554 0.023 Uiso 1 1 calc R . . C3 C 1.1343(2) 1.01860(13) 0.35079(10) 0.0172(5) Uani 1 1 d . . . H3B H 1.1628 1.0462 0.3924 0.021 Uiso 1 1 calc R . . H3C H 1.2083 0.9842 0.3380 0.021 Uiso 1 1 calc R . . C4 C 1.0132(2) 0.96060(12) 0.36089(9) 0.0142(4) Uani 1 1 d . . . C5 C 0.8990(2) 1.01992(13) 0.38002(10) 0.0156(4) Uani 1 1 d . . . H5A H 0.8188 0.9862 0.3836 0.019 Uiso 1 1 calc R . . H5B H 0.9244 1.0439 0.4233 0.019 Uiso 1 1 calc R . . C6 C 0.8650(2) 1.09283(13) 0.33098(10) 0.0184(5) Uani 1 1 d . . . H6A H 0.8236 1.0701 0.2897 0.022 Uiso 1 1 calc R . . H6B H 0.8015 1.1310 0.3492 0.022 Uiso 1 1 calc R . . C7 C 1.0456(2) 0.89771(12) 0.41838(9) 0.0146(4) Uani 1 1 d . . . C8 C 1.1752(2) 0.88180(13) 0.44538(10) 0.0172(5) Uani 1 1 d . . . H8A H 1.2466 0.9108 0.4292 0.021 Uiso 1 1 calc R . . C9 C 1.1999(2) 0.82319(13) 0.49618(10) 0.0179(5) Uani 1 1 d . . . H9A H 1.2874 0.8130 0.5136 0.021 Uiso 1 1 calc R . . C10 C 1.0945(2) 0.78005(13) 0.52084(10) 0.0172(5) Uani 1 1 d . . . C11 C 0.9631(2) 0.79287(13) 0.49453(10) 0.0176(5) Uani 1 1 d . . . C12 C 0.9418(2) 0.85185(13) 0.44373(10) 0.0178(5) Uani 1 1 d . . . H12A H 0.8544 0.8612 0.4258 0.021 Uiso 1 1 calc R . . C13 C 0.9743(2) 0.90903(12) 0.29754(10) 0.0142(4) Uani 1 1 d . . . C14 C 1.0733(2) 0.86827(12) 0.26420(10) 0.0160(5) Uani 1 1 d . . . H14A H 1.1621 0.8732 0.2813 0.019 Uiso 1 1 calc R . . C15 C 1.0457(2) 0.82105(12) 0.20702(10) 0.0157(4) Uani 1 1 d . . . C16 C 0.9119(2) 0.81265(12) 0.18226(10) 0.0164(5) Uani 1 1 d . . . C17 C 0.8113(2) 0.84975(13) 0.21528(10) 0.0176(5) Uani 1 1 d . . . H17A H 0.7221 0.8421 0.1996 0.021 Uiso 1 1 calc R . . C18 C 0.8425(2) 0.89807(12) 0.27148(10) 0.0155(4) Uani 1 1 d . . . H18A H 0.7737 0.9238 0.2923 0.019 Uiso 1 1 calc R . . C19 C 0.8477(2) 0.74368(14) 0.51908(11) 0.0241(5) Uani 1 1 d . . . H19A H 0.7654 0.7613 0.4953 0.036 Uiso 1 1 calc R . . H19B H 0.8432 0.7542 0.5655 0.036 Uiso 1 1 calc R . . H19C H 0.8611 0.6842 0.5120 0.036 Uiso 1 1 calc R . . C20 C 1.1543(2) 0.78216(14) 0.17002(11) 0.0234(5) Uani 1 1 d . . . H20A H 1.1392 0.7223 0.1657 0.035 Uiso 1 1 calc R . . H20B H 1.2398 0.7921 0.1939 0.035 Uiso 1 1 calc R . . H20C H 1.1532 0.8072 0.1268 0.035 Uiso 1 1 calc R . . C1A C 1.2209(2) 0.62248(13) 0.43583(10) 0.0180(5) Uani 1 1 d . . . C2A C 1.1198(2) 0.55747(13) 0.45274(10) 0.0183(5) Uani 1 1 d . . . H2AA H 1.0393 0.5851 0.4655 0.022 Uiso 1 1 calc R . . H2AB H 1.1562 0.5228 0.4895 0.022 Uiso 1 1 calc R . . C3A C 1.0864(2) 0.50186(13) 0.39097(10) 0.0179(5) Uani 1 1 d . . . H3AA H 1.0218 0.4590 0.4013 0.022 Uiso 1 1 calc R . . H3AB H 1.1672 0.4730 0.3799 0.022 Uiso 1 1 calc R . . C4A C 1.0286(2) 0.55339(12) 0.33006(10) 0.0150(4) Uani 1 1 d . . . C5A C 1.1341(2) 0.62275(13) 0.31812(10) 0.0165(5) Uani 1 1 d . . . H5AA H 1.2135 0.5954 0.3038 0.020 Uiso 1 1 calc R . . H5AB H 1.0981 0.6590 0.2823 0.020 Uiso 1 1 calc R . . C6A C 1.1758(2) 0.67828(13) 0.37837(10) 0.0173(5) Uani 1 1 d . . . H6AA H 1.2482 0.7157 0.3683 0.021 Uiso 1 1 calc R . . H6AB H 1.1006 0.7128 0.3894 0.021 Uiso 1 1 calc R . . C7A C 1.0143(2) 0.49872(13) 0.26719(10) 0.0151(4) Uani 1 1 d . . . C8A C 1.0334(2) 0.41155(13) 0.26730(10) 0.0163(5) Uani 1 1 d . . . H8AA H 1.0528 0.3835 0.3073 0.020 Uiso 1 1 calc R . . C9A C 1.0239(2) 0.36537(13) 0.20842(10) 0.0178(5) Uani 1 1 d . . . H9AA H 1.0361 0.3070 0.2096 0.021 Uiso 1 1 calc R . . C10A C 0.9965(2) 0.40584(13) 0.14832(10) 0.0173(5) Uani 1 1 d . . . C11A C 0.9781(2) 0.49428(13) 0.14588(10) 0.0164(5) Uani 1 1 d . . . C12A C 0.9854(2) 0.53808(13) 0.20556(10) 0.0168(5) Uani 1 1 d . . . H12B H 0.9703 0.5962 0.2046 0.020 Uiso 1 1 calc R . . C13A C 0.8907(2) 0.59094(13) 0.34293(10) 0.0152(4) Uani 1 1 d . . . C14A C 0.7936(2) 0.53835(13) 0.36758(10) 0.0166(5) Uani 1 1 d . . . H14B H 0.8146 0.4816 0.3754 0.020 Uiso 1 1 calc R . . C15A C 0.6675(2) 0.56715(13) 0.38081(10) 0.0173(5) Uani 1 1 d . . . C16A C 0.6382(2) 0.65256(13) 0.36920(10) 0.0177(5) Uani 1 1 d . . . C17A C 0.7295(2) 0.70466(13) 0.34209(10) 0.0188(5) Uani 1 1 d . . . H17B H 0.7070 0.7607 0.3325 0.023 Uiso 1 1 calc R . . C18A C 0.8544(2) 0.67457(13) 0.32900(10) 0.0173(5) Uani 1 1 d . . . H18B H 0.9149 0.7106 0.3107 0.021 Uiso 1 1 calc R . . C19A C 0.9555(2) 0.54003(14) 0.08082(10) 0.0232(5) Uani 1 1 d . . . H19D H 0.9454 0.5996 0.0888 0.035 Uiso 1 1 calc R . . H19E H 0.8757 0.5187 0.0568 0.035 Uiso 1 1 calc R . . H19F H 1.0309 0.5310 0.0553 0.035 Uiso 1 1 calc R . . C20A C 0.5655(2) 0.50767(13) 0.40648(11) 0.0225(5) Uani 1 1 d . . . H20D H 0.6033 0.4519 0.4113 0.034 Uiso 1 1 calc R . . H20E H 0.4871 0.5060 0.3758 0.034 Uiso 1 1 calc R . . H20F H 0.5413 0.5274 0.4487 0.034 Uiso 1 1 calc R . . H2 H 1.078(3) 0.7347(18) 0.6045(15) 0.061(10) Uiso 1 1 d . . . H3A H 0.478(3) 0.6629(19) 0.4114(15) 0.057(10) Uiso 1 1 d . . . H2A H 0.985(3) 0.3066(19) 0.0952(14) 0.056(9) Uiso 1 1 d . . . H3 H 0.802(3) 0.7711(19) 0.1104(15) 0.061(10) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0293(10) 0.0163(8) 0.0203(8) 0.0010(6) 0.0039(7) -0.0022(7) O2 0.0245(9) 0.0209(8) 0.0154(8) 0.0020(6) 0.0018(7) 0.0037(7) O3 0.0222(10) 0.0279(9) 0.0190(8) -0.0085(7) -0.0017(7) -0.0002(7) O1A 0.0177(9) 0.0268(9) 0.0234(8) 0.0009(7) 0.0011(7) -0.0001(7) O2A 0.0278(10) 0.0214(9) 0.0197(8) -0.0060(7) 0.0027(7) -0.0017(7) O3A 0.0167(9) 0.0212(8) 0.0346(9) 0.0080(7) 0.0097(7) 0.0039(7) C1 0.0227(13) 0.0189(11) 0.0115(10) 0.0010(8) 0.0010(9) -0.0015(9) C2 0.0221(13) 0.0183(11) 0.0189(11) -0.0004(9) 0.0057(9) -0.0026(9) C3 0.0157(12) 0.0184(11) 0.0178(11) -0.0043(8) 0.0024(9) -0.0025(9) C4 0.0131(11) 0.0151(10) 0.0147(10) -0.0003(8) 0.0017(8) 0.0004(8) C5 0.0138(11) 0.0181(10) 0.0151(10) 0.0001(8) 0.0022(8) -0.0019(9) C6 0.0206(13) 0.0157(10) 0.0190(11) -0.0019(9) 0.0011(9) 0.0011(9) C7 0.0160(12) 0.0150(10) 0.0126(10) -0.0034(8) 0.0003(8) -0.0010(9) C8 0.0145(12) 0.0199(11) 0.0173(11) -0.0036(9) 0.0022(9) -0.0017(9) C9 0.0161(12) 0.0205(11) 0.0166(10) -0.0048(9) -0.0019(9) 0.0017(9) C10 0.0219(13) 0.0160(10) 0.0136(10) -0.0011(8) 0.0008(9) 0.0024(9) C11 0.0202(13) 0.0185(11) 0.0143(10) -0.0018(8) 0.0034(9) -0.0015(9) C12 0.0127(12) 0.0223(11) 0.0184(11) -0.0015(9) 0.0009(9) 0.0010(9) C13 0.0154(12) 0.0134(10) 0.0138(10) 0.0015(8) 0.0010(8) -0.0015(9) C14 0.0132(12) 0.0165(10) 0.0182(10) 0.0002(8) 0.0008(9) -0.0011(9) C15 0.0176(12) 0.0138(10) 0.0161(10) 0.0013(8) 0.0034(9) 0.0001(9) C16 0.0212(13) 0.0137(10) 0.0141(10) 0.0002(8) -0.0002(9) -0.0010(9) C17 0.0144(12) 0.0168(10) 0.0211(11) 0.0021(9) -0.0005(9) -0.0002(9) C18 0.0150(12) 0.0148(10) 0.0173(10) -0.0001(8) 0.0045(9) 0.0014(9) C19 0.0205(13) 0.0281(12) 0.0238(12) 0.0064(10) 0.0017(10) -0.0022(10) C20 0.0209(13) 0.0240(12) 0.0257(12) -0.0059(10) 0.0050(10) -0.0012(10) C1A 0.0192(13) 0.0194(11) 0.0158(10) -0.0067(8) 0.0045(9) 0.0005(9) C2A 0.0173(12) 0.0239(11) 0.0139(10) 0.0021(8) 0.0017(9) -0.0003(9) C3A 0.0171(12) 0.0195(11) 0.0172(11) 0.0004(9) 0.0016(9) -0.0013(9) C4A 0.0141(12) 0.0147(10) 0.0165(10) 0.0008(8) 0.0030(8) -0.0008(8) C5A 0.0155(12) 0.0182(10) 0.0161(10) 0.0007(8) 0.0031(9) 0.0006(9) C6A 0.0154(12) 0.0169(10) 0.0196(11) -0.0012(9) 0.0008(9) -0.0002(9) C7A 0.0115(11) 0.0175(10) 0.0164(10) -0.0019(8) 0.0025(8) -0.0009(9) C8A 0.0125(11) 0.0182(11) 0.0183(11) 0.0014(8) 0.0015(9) -0.0003(9) C9A 0.0144(12) 0.0143(10) 0.0249(11) 0.0000(9) 0.0037(9) -0.0017(9) C10A 0.0120(11) 0.0216(11) 0.0187(11) -0.0052(9) 0.0036(9) -0.0011(9) C11A 0.0137(12) 0.0192(11) 0.0164(10) 0.0005(9) 0.0024(8) -0.0003(9) C12A 0.0152(12) 0.0155(10) 0.0198(11) 0.0011(8) 0.0033(9) 0.0014(9) C13A 0.0159(12) 0.0158(10) 0.0139(10) -0.0008(8) 0.0017(8) -0.0005(9) C14A 0.0198(12) 0.0145(10) 0.0154(10) -0.0006(8) 0.0005(9) 0.0001(9) C15A 0.0171(12) 0.0193(11) 0.0154(10) -0.0007(8) 0.0010(9) -0.0028(9) C16A 0.0143(12) 0.0211(11) 0.0178(11) 0.0005(9) 0.0025(9) 0.0020(9) C17A 0.0193(13) 0.0140(10) 0.0231(11) 0.0034(9) 0.0022(9) 0.0015(9) C18A 0.0181(12) 0.0182(11) 0.0158(10) 0.0024(8) 0.0028(9) -0.0036(9) C19A 0.0252(14) 0.0259(12) 0.0183(11) -0.0003(9) 0.0008(10) 0.0011(10) C20A 0.0231(13) 0.0182(11) 0.0270(12) 0.0032(9) 0.0063(10) 0.0000(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.232(2) . ? O2 C10 1.402(2) . ? O2 H2 0.88(3) . ? O3 C16 1.373(2) . ? O3 H3 0.88(3) . ? O1A C1A 1.227(3) . ? O2A C10A 1.375(2) . ? O2A H2A 0.91(3) . ? O3A C16A 1.385(3) . ? O3A H3A 0.84(3) . ? C1 C6 1.493(3) . ? C1 C2 1.496(3) . ? C2 C3 1.535(3) . ? C2 H2B 0.9700 . ? C2 H2C 0.9700 . ? C3 C4 1.546(3) . ? C3 H3B 0.9700 . ? C3 H3C 0.9700 . ? C4 C13 1.542(3) . ? C4 C7 1.544(3) . ? C4 C5 1.551(3) . ? C5 C6 1.539(3) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.388(3) . ? C7 C12 1.398(3) . ? C8 C9 1.390(3) . ? C8 H8A 0.9300 . ? C9 C10 1.383(3) . ? C9 H9A 0.9300 . ? C10 C11 1.392(3) . ? C11 C12 1.391(3) . ? C11 C19 1.509(3) . ? C12 H12A 0.9300 . ? C13 C18 1.390(3) . ? C13 C14 1.401(3) . ? C14 C15 1.385(3) . ? C14 H14A 0.9300 . ? C15 C16 1.396(3) . ? C15 C20 1.501(3) . ? C16 C17 1.384(3) . ? C17 C18 1.384(3) . ? C17 H17A 0.9300 . ? C18 H18A 0.9300 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C1A C6A 1.499(3) . ? C1A C2A 1.500(3) . ? C2A C3A 1.542(3) . ? C2A H2AA 0.9700 . ? C2A H2AB 0.9700 . ? C3A C4A 1.549(3) . ? C3A H3AA 0.9700 . ? C3A H3AB 0.9700 . ? C4A C7A 1.535(3) . ? C4A C13A 1.544(3) . ? C4A C5A 1.554(3) . ? C5A C6A 1.532(3) . ? C5A H5AA 0.9700 . ? C5A H5AB 0.9700 . ? C6A H6AA 0.9700 . ? C6A H6AB 0.9700 . ? C7A C8A 1.389(3) . ? C7A C12A 1.403(3) . ? C8A C9A 1.394(3) . ? C8A H8AA 0.9300 . ? C9A C10A 1.382(3) . ? C9A H9AA 0.9300 . ? C10A C11A 1.408(3) . ? C11A C12A 1.389(3) . ? C11A C19A 1.503(3) . ? C12A H12B 0.9300 . ? C13A C18A 1.391(3) . ? C13A C14A 1.401(3) . ? C14A C15A 1.388(3) . ? C14A H14B 0.9300 . ? C15A C16A 1.395(3) . ? C15A C20A 1.510(3) . ? C16A C17A 1.377(3) . ? C17A C18A 1.383(3) . ? C17A H17B 0.9300 . ? C18A H18B 0.9300 . ? C19A H19D 0.9600 . ? C19A H19E 0.9600 . ? C19A H19F 0.9600 . ? C20A H20D 0.9600 . ? C20A H20E 0.9600 . ? C20A H20F 0.9600 . ? 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 C10 O2 H2 106.9(19) . . ? C16 O3 H3 110.1(19) . . ? C10A O2A H2A 110.8(18) . . ? C16A O3A H3A 114(2) . . ? O1 C1 C6 123.7(2) . . ? O1 C1 C2 121.7(2) . . ? C6 C1 C2 114.51(18) . . ? C1 C2 C3 109.14(16) . . ? C1 C2 H2B 109.9 . . ? C3 C2 H2B 109.9 . . ? C1 C2 H2C 109.9 . . ? C3 C2 H2C 109.9 . . ? H2B C2 H2C 108.3 . . ? C2 C3 C4 112.33(17) . . ? C2 C3 H3B 109.1 . . ? C4 C3 H3B 109.1 . . ? C2 C3 H3C 109.1 . . ? C4 C3 H3C 109.1 . . ? H3B C3 H3C 107.9 . . ? C13 C4 C7 108.10(16) . . ? C13 C4 C3 110.39(16) . . ? C7 C4 C3 111.29(17) . . ? C13 C4 C5 112.76(17) . . ? C7 C4 C5 108.20(15) . . ? C3 C4 C5 106.12(16) . . ? C6 C5 C4 114.69(16) . . ? C6 C5 H5A 108.6 . . ? C4 C5 H5A 108.6 . . ? C6 C5 H5B 108.6 . . ? C4 C5 H5B 108.6 . . ? H5A C5 H5B 107.6 . . ? C1 C6 C5 110.46(18) . . ? C1 C6 H6A 109.6 . . ? C5 C6 H6A 109.6 . . ? C1 C6 H6B 109.6 . . ? C5 C6 H6B 109.6 . . ? H6A C6 H6B 108.1 . . ? C8 C7 C12 117.38(19) . . ? C8 C7 C4 122.95(18) . . ? C12 C7 C4 119.63(19) . . ? C7 C8 C9 120.96(19) . . ? C7 C8 H8A 119.5 . . ? C9 C8 H8A 119.5 . . ? C10 C9 C8 120.1(2) . . ? C10 C9 H9A 120.0 . . ? C8 C9 H9A 120.0 . . ? C9 C10 C11 120.97(19) . . ? C9 C10 O2 118.1(2) . . ? C11 C10 O2 120.86(18) . . ? C12 C11 C10 117.53(19) . . ? C12 C11 C19 120.9(2) . . ? C10 C11 C19 121.55(19) . . ? C11 C12 C7 123.1(2) . . ? C11 C12 H12A 118.5 . . ? C7 C12 H12A 118.5 . . ? C18 C13 C14 116.51(18) . . ? C18 C13 C4 123.18(18) . . ? C14 C13 C4 120.29(19) . . ? C15 C14 C13 123.4(2) . . ? C15 C14 H14A 118.3 . . ? C13 C14 H14A 118.3 . . ? C14 C15 C16 118.00(19) . . ? C14 C15 C20 122.4(2) . . ? C16 C15 C20 119.59(19) . . ? O3 C16 C17 122.9(2) . . ? O3 C16 C15 117.03(18) . . ? C17 C16 C15 120.04(19) . . ? C18 C17 C16 120.5(2) . . ? C18 C17 H17A 119.8 . . ? C16 C17 H17A 119.8 . . ? C17 C18 C13 121.51(19) . . ? C17 C18 H18A 119.2 . . ? C13 C18 H18A 119.2 . . ? C11 C19 H19A 109.5 . . ? C11 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C11 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C15 C20 H20A 109.5 . . ? C15 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C15 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? O1A C1A C6A 123.33(19) . . ? O1A C1A C2A 121.93(19) . . ? C6A C1A C2A 114.47(19) . . ? C1A C2A C3A 107.97(16) . . ? C1A C2A H2AA 110.1 . . ? C3A C2A H2AA 110.1 . . ? C1A C2A H2AB 110.1 . . ? C3A C2A H2AB 110.1 . . ? H2AA C2A H2AB 108.4 . . ? C2A C3A C4A 112.87(17) . . ? C2A C3A H3AA 109.0 . . ? C4A C3A H3AA 109.0 . . ? C2A C3A H3AB 109.0 . . ? C4A C3A H3AB 109.0 . . ? H3AA C3A H3AB 107.8 . . ? C7A C4A C13A 109.47(17) . . ? C7A C4A C3A 111.61(16) . . ? C13A C4A C3A 110.27(16) . . ? C7A C4A C5A 106.52(16) . . ? C13A C4A C5A 112.60(16) . . ? C3A C4A C5A 106.30(17) . . ? C6A C5A C4A 115.00(16) . . ? C6A C5A H5AA 108.5 . . ? C4A C5A H5AA 108.5 . . ? C6A C5A H5AB 108.5 . . ? C4A C5A H5AB 108.5 . . ? H5AA C5A H5AB 107.5 . . ? C1A C6A C5A 109.06(17) . . ? C1A C6A H6AA 109.9 . . ? C5A C6A H6AA 109.9 . . ? C1A C6A H6AB 109.9 . . ? C5A C6A H6AB 109.9 . . ? H6AA C6A H6AB 108.3 . . ? C8A C7A C12A 117.28(18) . . ? C8A C7A C4A 123.52(18) . . ? C12A C7A C4A 119.16(18) . . ? C7A C8A C9A 121.12(19) . . ? C7A C8A H8AA 119.4 . . ? C9A C8A H8AA 119.4 . . ? C10A C9A C8A 120.41(19) . . ? C10A C9A H9AA 119.8 . . ? C8A C9A H9AA 119.8 . . ? O2A C10A C9A 122.91(19) . . ? O2A C10A C11A 116.76(19) . . ? C9A C10A C11A 120.32(19) . . ? C12A C11A C10A 117.75(19) . . ? C12A C11A C19A 121.13(19) . . ? C10A C11A C19A 121.10(18) . . ? C11A C12A C7A 123.08(19) . . ? C11A C12A H12B 118.5 . . ? C7A C12A H12B 118.5 . . ? C18A C13A C14A 117.25(19) . . ? C18A C13A C4A 123.45(18) . . ? C14A C13A C4A 119.25(18) . . ? C15A C14A C13A 122.89(19) . . ? C15A C14A H14B 118.6 . . ? C13A C14A H14B 118.6 . . ? C14A C15A C16A 117.74(19) . . ? C14A C15A C20A 120.92(19) . . ? C16A C15A C20A 121.34(19) . . ? C17A C16A O3A 116.86(18) . . ? C17A C16A C15A 120.45(19) . . ? O3A C16A C15A 122.67(19) . . ? C16A C17A C18A 120.78(19) . . ? C16A C17A H17B 119.6 . . ? C18A C17A H17B 119.6 . . ? C17A C18A C13A 120.74(19) . . ? C17A C18A H18B 119.6 . . ? C13A C18A H18B 119.6 . . ? C11A C19A H19D 109.5 . . ? C11A C19A H19E 109.5 . . ? H19D C19A H19E 109.5 . . ? C11A C19A H19F 109.5 . . ? H19D C19A H19F 109.5 . . ? H19E C19A H19F 109.5 . . ? C15A C20A H20D 109.5 . . ? C15A C20A H20E 109.5 . . ? H20D C20A H20E 109.5 . . ? C15A C20A H20F 109.5 . . ? H20D C20A H20F 109.5 . . ? H20E C20A H20F 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 C3 120.0(2) . . . . ? C6 C1 C2 C3 -56.2(2) . . . . ? C1 C2 C3 C4 59.9(2) . . . . ? C2 C3 C4 C13 64.5(2) . . . . ? C2 C3 C4 C7 -175.46(16) . . . . ? C2 C3 C4 C5 -58.0(2) . . . . ? C13 C4 C5 C6 -66.8(2) . . . . ? C7 C4 C5 C6 173.73(16) . . . . ? C3 C4 C5 C6 54.2(2) . . . . ? O1 C1 C6 C5 -124.1(2) . . . . ? C2 C1 C6 C5 52.0(2) . . . . ? C4 C5 C6 C1 -51.8(2) . . . . ? C13 C4 C7 C8 106.4(2) . . . . ? C3 C4 C7 C8 -14.9(3) . . . . ? C5 C4 C7 C8 -131.2(2) . . . . ? C13 C4 C7 C12 -71.3(2) . . . . ? C3 C4 C7 C12 167.30(17) . . . . ? C5 C4 C7 C12 51.1(2) . . . . ? C12 C7 C8 C9 -0.8(3) . . . . ? C4 C7 C8 C9 -178.56(18) . . . . ? C7 C8 C9 C10 -0.4(3) . . . . ? C8 C9 C10 C11 1.5(3) . . . . ? C8 C9 C10 O2 178.71(17) . . . . ? C9 C10 C11 C12 -1.4(3) . . . . ? O2 C10 C11 C12 -178.55(18) . . . . ? C9 C10 C11 C19 177.50(19) . . . . ? O2 C10 C11 C19 0.4(3) . . . . ? C10 C11 C12 C7 0.2(3) . . . . ? C19 C11 C12 C7 -178.67(19) . . . . ? C8 C7 C12 C11 0.8(3) . . . . ? C4 C7 C12 C11 178.70(18) . . . . ? C7 C4 C13 C18 102.3(2) . . . . ? C3 C4 C13 C18 -135.78(19) . . . . ? C5 C4 C13 C18 -17.3(3) . . . . ? C7 C4 C13 C14 -75.8(2) . . . . ? C3 C4 C13 C14 46.1(2) . . . . ? C5 C4 C13 C14 164.59(17) . . . . ? C18 C13 C14 C15 1.9(3) . . . . ? C4 C13 C14 C15 -179.88(18) . . . . ? C13 C14 C15 C16 -1.2(3) . . . . ? C13 C14 C15 C20 176.38(19) . . . . ? C14 C15 C16 O3 179.01(18) . . . . ? C20 C15 C16 O3 1.4(3) . . . . ? C14 C15 C16 C17 -1.0(3) . . . . ? C20 C15 C16 C17 -178.68(19) . . . . ? O3 C16 C17 C18 -177.56(18) . . . . ? C15 C16 C17 C18 2.5(3) . . . . ? C16 C17 C18 C13 -1.8(3) . . . . ? C14 C13 C18 C17 -0.4(3) . . . . ? C4 C13 C18 C17 -178.56(18) . . . . ? O1A C1A C2A C3A -115.8(2) . . . . ? C6A C1A C2A C3A 58.4(2) . . . . ? C1A C2A C3A C4A -59.3(2) . . . . ? C2A C3A C4A C7A 172.27(16) . . . . ? C2A C3A C4A C13A -65.8(2) . . . . ? C2A C3A C4A C5A 56.5(2) . . . . ? C7A C4A C5A C6A -173.13(17) . . . . ? C13A C4A C5A C6A 66.9(2) . . . . ? C3A C4A C5A C6A -54.0(2) . . . . ? O1A C1A C6A C5A 118.7(2) . . . . ? C2A C1A C6A C5A -55.4(2) . . . . ? C4A C5A C6A C1A 53.6(2) . . . . ? C13A C4A C7A C8A -114.1(2) . . . . ? C3A C4A C7A C8A 8.3(3) . . . . ? C5A C4A C7A C8A 123.9(2) . . . . ? C13A C4A C7A C12A 68.4(2) . . . . ? C3A C4A C7A C12A -169.24(18) . . . . ? C5A C4A C7A C12A -53.6(2) . . . . ? C12A C7A C8A C9A -0.1(3) . . . . ? C4A C7A C8A C9A -177.64(18) . . . . ? C7A C8A C9A C10A 0.7(3) . . . . ? C8A C9A C10A O2A -179.58(19) . . . . ? C8A C9A C10A C11A 0.2(3) . . . . ? O2A C10A C11A C12A 178.23(17) . . . . ? C9A C10A C11A C12A -1.5(3) . . . . ? O2A C10A C11A C19A -3.5(3) . . . . ? C9A C10A C11A C19A 176.72(19) . . . . ? C10A C11A C12A C7A 2.2(3) . . . . ? C19A C11A C12A C7A -176.05(19) . . . . ? C8A C7A C12A C11A -1.4(3) . . . . ? C4A C7A C12A C11A 176.29(19) . . . . ? C7A C4A C13A C18A -103.0(2) . . . . ? C3A C4A C13A C18A 133.9(2) . . . . ? C5A C4A C13A C18A 15.3(3) . . . . ? C7A C4A C13A C14A 74.5(2) . . . . ? C3A C4A C13A C14A -48.6(2) . . . . ? C5A C4A C13A C14A -167.19(18) . . . . ? C18A C13A C14A C15A -2.7(3) . . . . ? C4A C13A C14A C15A 179.67(18) . . . . ? C13A C14A C15A C16A -0.5(3) . . . . ? C13A C14A C15A C20A 179.15(19) . . . . ? C14A C15A C16A C17A 3.5(3) . . . . ? C20A C15A C16A C17A -176.1(2) . . . . ? C14A C15A C16A O3A -177.99(19) . . . . ? C20A C15A C16A O3A 2.4(3) . . . . ? O3A C16A C17A C18A 178.09(19) . . . . ? C15A C16A C17A C18A -3.3(3) . . . . ? C16A C17A C18A C13A 0.0(3) . . . . ? C14A C13A C18A C17A 2.9(3) . . . . ? C4A C13A C18A C17A -179.55(19) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.217 _refine_diff_density_min -0.235 _refine_diff_density_rms 0.047