# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2006 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _publ_contact_author_name A.Nangia _publ_contact_author_address ; School of Chemistry University of Hyderabad P O Central University Hyderabad 500046 Hyderabad INDIA ; _publ_section_title ; Polymorphs of 1,1-bis(4-hydroxyphenyl)cyclohexane and multiple Z' structures by melt and sublimation crystallization ; _publ_contact_author_email ASHWINI_NANGIA@REDIFFMAIL.COM loop_ _publ_author_name A.Nangia S.Roy B.Sarma # Attachment 'an464_m melt.cif' data_an464_m _database_code_depnum_ccdc_archive 'CCDC 615422' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,1-bis(4-Hydroxyphenyl)cyclohexane ; _chemical_name_common 1,1-bis(4-Hydroxyphenyl)cyclohexane _chemical_melting_point ? _chemical_formula_moiety 'C18 H20 O2' _chemical_formula_sum 'C18 H20 O2' _chemical_formula_weight 268.34 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'Pbca ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 9.6278(5) _cell_length_b 20.9561(11) _cell_length_c 28.0324(14) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 5655.8(5) _cell_formula_units_Z 16 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 7303 _cell_measurement_theta_min 2.74 _cell_measurement_theta_max 25.75 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.261 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2304 _exptl_absorpt_coefficient_mu 0.080 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9701 _exptl_absorpt_correction_T_max 0.9928 _exptl_absorpt_process_details 'SADABS - Bruker Nonius area detector scaling and absorption correction - V2.10' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 51362 _diffrn_reflns_av_R_equivalents 0.0660 _diffrn_reflns_av_sigmaI/netI 0.0306 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -33 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_theta_min 1.45 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4984 _reflns_number_gt 4167 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0416P)^2^+4.0457P] 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 4984 _refine_ls_number_parameters 377 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0715 _refine_ls_R_factor_gt 0.0582 _refine_ls_wR_factor_ref 0.1217 _refine_ls_wR_factor_gt 0.1164 _refine_ls_goodness_of_fit_ref 1.201 _refine_ls_restrained_S_all 1.201 _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 O2B O 0.88544(17) 1.18242(7) 0.74110(6) 0.0207(4) Uani 1 1 d . . . O2A O 0.41695(17) -0.10443(7) 0.68163(6) 0.0232(4) Uani 1 1 d . . . O1A O 0.01748(16) 0.28337(8) 0.63023(6) 0.0225(4) Uani 1 1 d . . . O1B O 0.86530(17) 0.74456(7) 0.74674(6) 0.0212(4) Uani 1 1 d . . . C10A C 0.1353(2) 0.24898(10) 0.61985(8) 0.0164(5) Uani 1 1 d . . . C18A C 0.4723(2) 0.01022(10) 0.58602(8) 0.0173(5) Uani 1 1 d . . . H18A H 0.4848 0.0095 0.5524 0.021 Uiso 1 1 calc R . . C7B C 0.9183(2) 0.90221(10) 0.65675(8) 0.0150(5) Uani 1 1 d . . . C13B C 0.9373(2) 1.01970(10) 0.65655(8) 0.0149(5) Uani 1 1 d . . . C11A C 0.1238(2) 0.19753(10) 0.58910(8) 0.0184(5) Uani 1 1 d . . . H11A H 0.0362 0.1867 0.5758 0.022 Uiso 1 1 calc R . . C9B C 0.7784(2) 0.81205(10) 0.68322(8) 0.0161(5) Uani 1 1 d . . . H9B H 0.6969 0.7868 0.6800 0.019 Uiso 1 1 calc R . . C15A C 0.4335(2) 0.01097(11) 0.68354(8) 0.0181(5) Uani 1 1 d . . . H15A H 0.4193 0.0115 0.7171 0.022 Uiso 1 1 calc R . . C15B C 0.7965(2) 1.08638(10) 0.70815(8) 0.0169(5) Uani 1 1 d . . . H15B H 0.7107 1.0942 0.7239 0.020 Uiso 1 1 calc R . . C1B C 0.9477(2) 0.96016(10) 0.62488(8) 0.0151(5) Uani 1 1 d . . . C13A C 0.4719(2) 0.06849(10) 0.60957(8) 0.0157(5) Uani 1 1 d . . . C7A C 0.3708(2) 0.17598(10) 0.59659(7) 0.0146(5) Uani 1 1 d . . . C17A C 0.4549(2) -0.04721(10) 0.61033(8) 0.0178(5) Uani 1 1 d . . . H17A H 0.4554 -0.0865 0.5935 0.021 Uiso 1 1 calc R . . C8A C 0.3785(2) 0.22711(10) 0.62811(8) 0.0170(5) Uani 1 1 d . . . H8A H 0.4655 0.2375 0.6421 0.020 Uiso 1 1 calc R . . C16B C 0.9060(2) 1.12873(10) 0.71309(7) 0.0155(5) Uani 1 1 d . . . C16A C 0.4369(2) -0.04639(10) 0.65915(8) 0.0170(5) Uani 1 1 d . . . C18B C 1.0462(2) 1.06270(10) 0.66279(8) 0.0166(5) Uani 1 1 d . . . H18B H 1.1327 1.0547 0.6476 0.020 Uiso 1 1 calc R . . C11B C 0.9951(2) 0.83436(10) 0.72204(8) 0.0161(5) Uani 1 1 d . . . H11B H 1.0625 0.8244 0.7456 0.019 Uiso 1 1 calc R . . C14B C 0.8130(2) 1.03283(10) 0.68020(8) 0.0164(5) Uani 1 1 d . . . H14B H 0.7375 1.0040 0.6769 0.020 Uiso 1 1 calc R . . C14A C 0.4509(2) 0.06741(10) 0.65889(8) 0.0175(5) Uani 1 1 d . . . H14A H 0.4485 0.1066 0.6759 0.021 Uiso 1 1 calc R . . C17B C 1.0309(2) 1.11692(10) 0.69073(8) 0.0170(5) Uani 1 1 d . . . H17B H 1.1063 1.1458 0.6944 0.020 Uiso 1 1 calc R . . C6B C 1.0926(2) 0.95309(10) 0.60170(8) 0.0175(5) Uani 1 1 d . . . H6BB H 1.1164 0.9932 0.5849 0.021 Uiso 1 1 calc R . . H6BA H 1.1627 0.9463 0.6270 0.021 Uiso 1 1 calc R . . C9A C 0.2628(2) 0.26331(10) 0.63968(8) 0.0173(5) Uani 1 1 d . . . H9A H 0.2713 0.2980 0.6613 0.021 Uiso 1 1 calc R . . C5B C 1.0991(2) 0.89788(11) 0.56653(8) 0.0206(5) Uani 1 1 d . . . H5BA H 1.0765 0.8576 0.5833 0.025 Uiso 1 1 calc R . . H5BB H 1.1946 0.8942 0.5537 0.025 Uiso 1 1 calc R . . C2B C 0.8424(2) 0.96825(10) 0.58345(8) 0.0162(5) Uani 1 1 d . . . H2BA H 0.7474 0.9681 0.5970 0.019 Uiso 1 1 calc R . . H2BB H 0.8575 1.0105 0.5686 0.019 Uiso 1 1 calc R . . C12A C 0.2400(2) 0.16207(11) 0.57787(7) 0.0165(5) Uani 1 1 d . . . H12A H 0.2306 0.1270 0.5567 0.020 Uiso 1 1 calc R . . C10B C 0.8767(2) 0.79688(10) 0.71722(8) 0.0147(5) Uani 1 1 d . . . C2A C 0.6363(2) 0.16068(10) 0.60244(8) 0.0173(5) Uani 1 1 d . . . H2AA H 0.6276 0.1703 0.6369 0.021 Uiso 1 1 calc R . . H2AB H 0.7091 0.1276 0.5988 0.021 Uiso 1 1 calc R . . C5A C 0.5489(2) 0.18703(11) 0.50472(8) 0.0216(5) Uani 1 1 d . . . H5AB H 0.5545 0.1795 0.4699 0.026 Uiso 1 1 calc R . . H5AA H 0.4760 0.2194 0.5106 0.026 Uiso 1 1 calc R . . C12B C 1.0138(2) 0.88614(10) 0.69228(8) 0.0155(5) Uani 1 1 d . . . H12B H 1.0945 0.9117 0.6961 0.019 Uiso 1 1 calc R . . C1A C 0.4960(2) 0.13300(10) 0.58434(8) 0.0151(5) Uani 1 1 d . . . C8B C 0.7993(2) 0.86441(10) 0.65370(8) 0.0151(5) Uani 1 1 d . . . H8B H 0.7304 0.8748 0.6307 0.018 Uiso 1 1 calc R . . C6A C 0.5100(2) 0.12508(10) 0.52982(8) 0.0176(5) Uani 1 1 d . . . H6AB H 0.5819 0.0926 0.5230 0.021 Uiso 1 1 calc R . . H6AA H 0.4208 0.1093 0.5168 0.021 Uiso 1 1 calc R . . C3A C 0.6837(2) 0.22119(11) 0.57652(8) 0.0198(5) Uani 1 1 d . . . H3AA H 0.6192 0.2565 0.5842 0.024 Uiso 1 1 calc R . . H3AB H 0.7773 0.2333 0.5880 0.024 Uiso 1 1 calc R . . C3B C 0.8503(2) 0.91720(11) 0.54447(8) 0.0206(5) Uani 1 1 d . . . H3BA H 0.8158 0.8762 0.5575 0.025 Uiso 1 1 calc R . . H3BB H 0.7888 0.9296 0.5177 0.025 Uiso 1 1 calc R . . C4B C 0.9976(2) 0.90771(12) 0.52554(8) 0.0241(5) Uani 1 1 d . . . H4BA H 0.9998 0.8701 0.5042 0.029 Uiso 1 1 calc R . . H4BB H 1.0257 0.9456 0.5068 0.029 Uiso 1 1 calc R . . C4A C 0.6879(2) 0.21186(11) 0.52281(8) 0.0227(5) Uani 1 1 d . . . H4AA H 0.7622 0.1811 0.5146 0.027 Uiso 1 1 calc R . . H4AB H 0.7096 0.2530 0.5071 0.027 Uiso 1 1 calc R . . H2B H 0.964(3) 1.2018(14) 0.7437(11) 0.045(9) Uiso 1 1 d . . . H2A H 0.424(3) -0.1005(13) 0.7129(11) 0.038(8) Uiso 1 1 d . . . H1B H 0.787(3) 0.7271(12) 0.7427(9) 0.025(7) Uiso 1 1 d . . . H1A H 0.041(3) 0.3162(14) 0.6481(10) 0.040(8) 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 O2B 0.0200(9) 0.0157(8) 0.0263(9) -0.0053(7) -0.0010(7) -0.0001(7) O2A 0.0300(10) 0.0164(8) 0.0231(10) 0.0035(7) -0.0006(7) -0.0022(7) O1A 0.0155(8) 0.0213(9) 0.0306(10) -0.0046(8) 0.0009(7) 0.0035(7) O1B 0.0171(8) 0.0193(9) 0.0272(9) 0.0055(7) -0.0017(7) -0.0024(7) C10A 0.0153(11) 0.0171(11) 0.0167(11) 0.0044(9) 0.0051(9) 0.0031(9) C18A 0.0121(11) 0.0209(12) 0.0190(12) -0.0022(9) -0.0004(9) 0.0006(9) C7B 0.0142(11) 0.0139(11) 0.0169(11) -0.0036(9) 0.0019(9) 0.0043(9) C13B 0.0150(11) 0.0146(11) 0.0151(11) 0.0039(9) -0.0019(9) 0.0012(9) C11A 0.0130(11) 0.0219(12) 0.0201(12) 0.0018(10) -0.0022(9) -0.0016(9) C9B 0.0124(11) 0.0176(11) 0.0182(11) -0.0025(9) 0.0011(9) -0.0020(9) C15A 0.0140(11) 0.0238(12) 0.0164(11) -0.0002(10) -0.0005(9) 0.0004(9) C15B 0.0132(10) 0.0189(12) 0.0185(12) 0.0004(9) -0.0002(9) 0.0037(9) C1B 0.0128(11) 0.0141(11) 0.0184(11) 0.0004(9) -0.0006(9) -0.0006(9) C13A 0.0071(10) 0.0203(12) 0.0197(12) -0.0015(9) -0.0030(9) 0.0004(9) C7A 0.0169(11) 0.0127(11) 0.0143(11) 0.0038(9) 0.0004(9) 0.0004(9) C17A 0.0138(11) 0.0152(11) 0.0245(13) -0.0045(9) -0.0021(9) 0.0011(9) C8A 0.0132(11) 0.0172(11) 0.0206(12) 0.0013(9) -0.0012(9) -0.0020(9) C16B 0.0221(12) 0.0111(11) 0.0134(11) 0.0023(9) -0.0046(9) 0.0034(9) C16A 0.0112(11) 0.0159(12) 0.0238(12) 0.0010(9) -0.0020(9) 0.0002(9) C18B 0.0134(11) 0.0177(11) 0.0187(12) 0.0012(9) 0.0015(9) 0.0000(9) C11B 0.0158(11) 0.0168(11) 0.0157(11) -0.0020(9) -0.0030(9) 0.0045(9) C14B 0.0127(11) 0.0154(11) 0.0211(12) 0.0013(9) -0.0031(9) -0.0015(9) C14A 0.0158(11) 0.0148(11) 0.0219(12) -0.0031(9) -0.0016(9) 0.0020(9) C17B 0.0167(11) 0.0147(11) 0.0195(12) 0.0030(9) -0.0017(9) -0.0051(9) C6B 0.0137(11) 0.0193(12) 0.0193(12) 0.0008(9) 0.0010(9) 0.0005(9) C9A 0.0207(12) 0.0132(11) 0.0180(11) -0.0025(9) 0.0018(9) -0.0011(9) C5B 0.0172(12) 0.0217(12) 0.0229(12) -0.0017(10) 0.0027(10) 0.0024(9) C2B 0.0142(11) 0.0151(11) 0.0194(12) 0.0032(9) -0.0021(9) 0.0002(9) C12A 0.0193(11) 0.0167(11) 0.0136(11) -0.0021(9) -0.0013(9) -0.0022(9) C10B 0.0157(11) 0.0130(11) 0.0154(11) -0.0002(9) 0.0038(9) 0.0044(9) C2A 0.0143(11) 0.0193(11) 0.0183(11) -0.0025(9) -0.0008(9) 0.0028(9) C5A 0.0230(12) 0.0247(13) 0.0170(12) 0.0007(10) 0.0014(10) 0.0018(10) C12B 0.0116(10) 0.0154(11) 0.0196(12) -0.0040(9) 0.0002(9) 0.0003(9) C1A 0.0140(11) 0.0145(11) 0.0166(11) -0.0013(9) -0.0015(9) -0.0002(9) C8B 0.0120(10) 0.0159(11) 0.0173(11) -0.0019(9) -0.0011(9) 0.0023(9) C6A 0.0145(11) 0.0182(11) 0.0203(12) -0.0048(9) 0.0000(9) 0.0000(9) C3A 0.0145(11) 0.0190(12) 0.0259(13) -0.0024(10) 0.0008(9) -0.0025(9) C3B 0.0207(12) 0.0228(12) 0.0185(12) -0.0003(10) -0.0050(9) 0.0003(10) C4B 0.0293(13) 0.0231(12) 0.0199(12) -0.0044(10) 0.0002(10) 0.0019(11) C4A 0.0230(13) 0.0191(12) 0.0261(13) 0.0017(10) 0.0050(10) -0.0022(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 O2B C16B 1.386(3) . ? O2B H2B 0.87(3) . ? O2A C16A 1.383(3) . ? O2A H2A 0.88(3) . ? O1A C10A 1.375(3) . ? O1A H1A 0.88(3) . ? O1B C10B 1.378(3) . ? O1B H1B 0.84(3) . ? C10A C9A 1.381(3) . ? C10A C11A 1.385(3) . ? C18A C13A 1.388(3) . ? C18A C17A 1.393(3) . ? C18A H18A 0.9500 . ? C7B C8B 1.396(3) . ? C7B C12B 1.397(3) . ? C7B C1B 1.534(3) . ? C13B C18B 1.393(3) . ? C13B C14B 1.396(3) . ? C13B C1B 1.535(3) . ? C11A C12A 1.379(3) . ? C11A H11A 0.9500 . ? C9B C10B 1.380(3) . ? C9B C8B 1.389(3) . ? C9B H9B 0.9500 . ? C15A C14A 1.380(3) . ? C15A C16A 1.383(3) . ? C15A H15A 0.9500 . ? C15B C14B 1.378(3) . ? C15B C16B 1.385(3) . ? C15B H15B 0.9500 . ? C1B C6B 1.546(3) . ? C1B C2B 1.551(3) . ? C13A C14A 1.397(3) . ? C13A C1A 1.543(3) . ? C7A C8A 1.391(3) . ? C7A C12A 1.395(3) . ? C7A C1A 1.544(3) . ? C17A C16A 1.380(3) . ? C17A H17A 0.9500 . ? C8A C9A 1.386(3) . ? C8A H8A 0.9500 . ? C16B C17B 1.379(3) . ? C18B C17B 1.388(3) . ? C18B H18B 0.9500 . ? C11B C12B 1.381(3) . ? C11B C10B 1.391(3) . ? C11B H11B 0.9500 . ? C14B H14B 0.9500 . ? C14A H14A 0.9500 . ? C17B H17B 0.9500 . ? C6B C5B 1.521(3) . ? C6B H6BB 0.9900 . ? C6B H6BA 0.9900 . ? C9A H9A 0.9500 . ? C5B C4B 1.523(3) . ? C5B H5BA 0.9900 . ? C5B H5BB 0.9900 . ? C2B C3B 1.531(3) . ? C2B H2BA 0.9900 . ? C2B H2BB 0.9900 . ? C12A H12A 0.9500 . ? C2A C3A 1.531(3) . ? C2A C1A 1.555(3) . ? C2A H2AA 0.9900 . ? C2A H2AB 0.9900 . ? C5A C4A 1.523(3) . ? C5A C6A 1.523(3) . ? C5A H5AB 0.9900 . ? C5A H5AA 0.9900 . ? C12B H12B 0.9500 . ? C1A C6A 1.543(3) . ? C8B H8B 0.9500 . ? C6A H6AB 0.9900 . ? C6A H6AA 0.9900 . ? C3A C4A 1.519(3) . ? C3A H3AA 0.9900 . ? C3A H3AB 0.9900 . ? C3B C4B 1.527(3) . ? C3B H3BA 0.9900 . ? C3B H3BB 0.9900 . ? C4B H4BA 0.9900 . ? C4B H4BB 0.9900 . ? C4A H4AA 0.9900 . ? C4A H4AB 0.9900 . ? 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 C16B O2B H2B 108(2) . . ? C16A O2A H2A 111.1(18) . . ? C10A O1A H1A 108.6(19) . . ? C10B O1B H1B 109.6(17) . . ? O1A C10A C9A 122.3(2) . . ? O1A C10A C11A 118.3(2) . . ? C9A C10A C11A 119.4(2) . . ? C13A C18A C17A 121.8(2) . . ? C13A C18A H18A 119.1 . . ? C17A C18A H18A 119.1 . . ? C8B C7B C12B 116.6(2) . . ? C8B C7B C1B 124.42(19) . . ? C12B C7B C1B 118.98(19) . . ? C18B C13B C14B 117.3(2) . . ? C18B C13B C1B 123.34(19) . . ? C14B C13B C1B 119.41(19) . . ? C12A C11A C10A 119.8(2) . . ? C12A C11A H11A 120.1 . . ? C10A C11A H11A 120.1 . . ? C10B C9B C8B 119.6(2) . . ? C10B C9B H9B 120.2 . . ? C8B C9B H9B 120.2 . . ? C14A C15A C16A 119.6(2) . . ? C14A C15A H15A 120.2 . . ? C16A C15A H15A 120.2 . . ? C14B C15B C16B 119.4(2) . . ? C14B C15B H15B 120.3 . . ? C16B C15B H15B 120.3 . . ? C7B C1B C13B 107.14(17) . . ? C7B C1B C6B 109.60(17) . . ? C13B C1B C6B 112.32(17) . . ? C7B C1B C2B 113.69(17) . . ? C13B C1B C2B 107.56(17) . . ? C6B C1B C2B 106.61(17) . . ? C18A C13A C14A 117.2(2) . . ? C18A C13A C1A 123.52(19) . . ? C14A C13A C1A 119.30(19) . . ? C8A C7A C12A 116.6(2) . . ? C8A C7A C1A 123.30(19) . . ? C12A C7A C1A 119.95(19) . . ? C16A C17A C18A 119.3(2) . . ? C16A C17A H17A 120.3 . . ? C18A C17A H17A 120.3 . . ? C9A C8A C7A 121.8(2) . . ? C9A C8A H8A 119.1 . . ? C7A C8A H8A 119.1 . . ? C17B C16B C15B 120.2(2) . . ? C17B C16B O2B 121.9(2) . . ? C15B C16B O2B 117.91(19) . . ? C17A C16A O2A 117.3(2) . . ? C17A C16A C15A 120.3(2) . . ? O2A C16A C15A 122.4(2) . . ? C17B C18B C13B 121.4(2) . . ? C17B C18B H18B 119.3 . . ? C13B C18B H18B 119.3 . . ? C12B C11B C10B 119.5(2) . . ? C12B C11B H11B 120.3 . . ? C10B C11B H11B 120.3 . . ? C15B C14B C13B 122.0(2) . . ? C15B C14B H14B 119.0 . . ? C13B C14B H14B 119.0 . . ? C15A C14A C13A 121.8(2) . . ? C15A C14A H14A 119.1 . . ? C13A C14A H14A 119.1 . . ? C16B C17B C18B 119.7(2) . . ? C16B C17B H17B 120.1 . . ? C18B C17B H17B 120.1 . . ? C5B C6B C1B 112.47(18) . . ? C5B C6B H6BB 109.1 . . ? C1B C6B H6BB 109.1 . . ? C5B C6B H6BA 109.1 . . ? C1B C6B H6BA 109.1 . . ? H6BB C6B H6BA 107.8 . . ? C10A C9A C8A 120.1(2) . . ? C10A C9A H9A 120.0 . . ? C8A C9A H9A 120.0 . . ? C6B C5B C4B 111.08(18) . . ? C6B C5B H5BA 109.4 . . ? C4B C5B H5BA 109.4 . . ? C6B C5B H5BB 109.4 . . ? C4B C5B H5BB 109.4 . . ? H5BA C5B H5BB 108.0 . . ? C3B C2B C1B 115.18(18) . . ? C3B C2B H2BA 108.5 . . ? C1B C2B H2BA 108.5 . . ? C3B C2B H2BB 108.5 . . ? C1B C2B H2BB 108.5 . . ? H2BA C2B H2BB 107.5 . . ? C11A C12A C7A 122.2(2) . . ? C11A C12A H12A 118.9 . . ? C7A C12A H12A 118.9 . . ? O1B C10B C9B 122.91(19) . . ? O1B C10B C11B 117.14(19) . . ? C9B C10B C11B 119.9(2) . . ? C3A C2A C1A 114.38(18) . . ? C3A C2A H2AA 108.7 . . ? C1A C2A H2AA 108.7 . . ? C3A C2A H2AB 108.7 . . ? C1A C2A H2AB 108.7 . . ? H2AA C2A H2AB 107.6 . . ? C4A C5A C6A 110.68(19) . . ? C4A C5A H5AB 109.5 . . ? C6A C5A H5AB 109.5 . . ? C4A C5A H5AA 109.5 . . ? C6A C5A H5AA 109.5 . . ? H5AB C5A H5AA 108.1 . . ? C11B C12B C7B 122.3(2) . . ? C11B C12B H12B 118.9 . . ? C7B C12B H12B 118.9 . . ? C13A C1A C6A 111.88(17) . . ? C13A C1A C7A 106.98(17) . . ? C6A C1A C7A 110.58(17) . . ? C13A C1A C2A 107.92(17) . . ? C6A C1A C2A 106.68(17) . . ? C7A C1A C2A 112.85(17) . . ? C9B C8B C7B 122.1(2) . . ? C9B C8B H8B 119.0 . . ? C7B C8B H8B 119.0 . . ? C5A C6A C1A 112.78(18) . . ? C5A C6A H6AB 109.0 . . ? C1A C6A H6AB 109.0 . . ? C5A C6A H6AA 109.0 . . ? C1A C6A H6AA 109.0 . . ? H6AB C6A H6AA 107.8 . . ? C4A C3A C2A 111.83(18) . . ? C4A C3A H3AA 109.3 . . ? C2A C3A H3AA 109.3 . . ? C4A C3A H3AB 109.3 . . ? C2A C3A H3AB 109.3 . . ? H3AA C3A H3AB 107.9 . . ? C4B C3B C2B 112.66(18) . . ? C4B C3B H3BA 109.1 . . ? C2B C3B H3BA 109.1 . . ? C4B C3B H3BB 109.1 . . ? C2B C3B H3BB 109.1 . . ? H3BA C3B H3BB 107.8 . . ? C5B C4B C3B 110.58(19) . . ? C5B C4B H4BA 109.5 . . ? C3B C4B H4BA 109.5 . . ? C5B C4B H4BB 109.5 . . ? C3B C4B H4BB 109.5 . . ? H4BA C4B H4BB 108.1 . . ? C3A C4A C5A 110.51(19) . . ? C3A C4A H4AA 109.5 . . ? C5A C4A H4AA 109.5 . . ? C3A C4A H4AB 109.5 . . ? C5A C4A H4AB 109.5 . . ? H4AA C4A H4AB 108.1 . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.287 _refine_diff_density_min -0.277 _refine_diff_density_rms 0.050 # Attachment 'an540_m sublimed.cif' data_an540_m _database_code_depnum_ccdc_archive 'CCDC 620074' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,1-Bis(4-Hydroxypheyl)cyclohexane ; _chemical_name_common 1,1-Bis(4-Hydroxypheyl)cyclohexane _chemical_melting_point ? _chemical_formula_moiety 'C18 H20 O2' _chemical_formula_sum 'C18 H20 O2' _chemical_formula_weight 268.34 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 6.2275(6) _cell_length_b 10.8480(10) _cell_length_c 11.3359(11) _cell_angle_alpha 101.611(2) _cell_angle_beta 103.4240(10) _cell_angle_gamma 103.117(2) _cell_volume 698.90(12) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3782 _cell_measurement_theta_min 2.37 _cell_measurement_theta_max 26.09 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.275 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 288 _exptl_absorpt_coefficient_mu 0.081 _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(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7287 _diffrn_reflns_av_R_equivalents 0.0253 _diffrn_reflns_av_sigmaI/netI 0.0316 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.92 _diffrn_reflns_theta_max 26.09 _reflns_number_total 2753 _reflns_number_gt 2255 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0685P)^2^+0.1357P] 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 2753 _refine_ls_number_parameters 261 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0530 _refine_ls_R_factor_gt 0.0424 _refine_ls_wR_factor_ref 0.1189 _refine_ls_wR_factor_gt 0.1117 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.046 _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_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.34828(19) 1.12276(10) 0.07498(10) 0.0236(3) Uani 1 1 d . . . C1 C 0.1698(2) 0.76013(14) 0.36819(13) 0.0161(3) Uani 1 1 d . . . O2 O 0.0315(2) 0.26111(11) 0.03043(11) 0.0280(3) Uani 1 1 d . . . C11 C 0.1144(2) 1.03105(14) 0.19700(14) 0.0196(3) Uani 1 1 d . . . C7 C 0.2082(2) 0.85903(13) 0.28952(13) 0.0162(3) Uani 1 1 d . . . C2 C 0.3853(2) 0.79910(14) 0.48407(13) 0.0171(3) Uani 1 1 d . . . C17 C 0.2662(2) 0.43973(14) 0.20165(14) 0.0200(3) Uani 1 1 d . . . C12 C 0.0728(2) 0.94323(14) 0.26885(14) 0.0181(3) Uani 1 1 d . . . C15 C -0.1191(3) 0.43998(15) 0.10424(14) 0.0213(3) Uani 1 1 d . . . C10 C 0.2961(2) 1.03756(14) 0.14471(13) 0.0182(3) Uani 1 1 d . . . C8 C 0.3884(2) 0.86688(14) 0.23458(13) 0.0179(3) Uani 1 1 d . . . C14 C -0.0809(2) 0.56015(15) 0.18785(14) 0.0192(3) Uani 1 1 d . . . C13 C 0.1289(2) 0.62294(13) 0.28134(13) 0.0161(3) Uani 1 1 d . . . C9 C 0.4334(2) 0.95423(14) 0.16355(14) 0.0189(3) Uani 1 1 d . . . C6 C -0.0367(2) 0.76566(15) 0.42082(14) 0.0184(3) Uani 1 1 d . . . C5 C -0.0638(3) 0.67694(15) 0.50840(15) 0.0210(3) Uani 1 1 d . . . C16 C 0.0556(3) 0.37982(14) 0.11093(13) 0.0200(3) Uani 1 1 d . . . C18 C 0.3006(2) 0.55892(14) 0.28557(14) 0.0185(3) Uani 1 1 d . . . C3 C 0.3639(2) 0.71390(15) 0.57503(14) 0.0190(3) Uani 1 1 d . . . C4 C 0.1515(2) 0.71526(16) 0.62019(14) 0.0215(3) Uani 1 1 d . . . H3A H 0.352(3) 0.6229(16) 0.5336(14) 0.013(4) Uiso 1 1 d . . . H17 H 0.388(3) 0.3945(16) 0.2060(15) 0.021(4) Uiso 1 1 d . . . H2A H 0.524(3) 0.7978(15) 0.4558(14) 0.017(4) Uiso 1 1 d . . . H2B H 0.405(3) 0.8903(16) 0.5281(15) 0.017(4) Uiso 1 1 d . . . H5A H -0.098(3) 0.5796(16) 0.4595(15) 0.021(4) Uiso 1 1 d . . . H6B H -0.014(3) 0.8573(15) 0.4690(14) 0.013(4) Uiso 1 1 d . . . H6A H -0.183(3) 0.7434(15) 0.3502(15) 0.015(4) Uiso 1 1 d . . . H4B H 0.174(3) 0.8067(17) 0.6732(15) 0.022(4) Uiso 1 1 d . . . H3B H 0.502(3) 0.7467(15) 0.6488(15) 0.020(4) Uiso 1 1 d . . . H8 H 0.483(3) 0.8066(15) 0.2440(14) 0.017(4) Uiso 1 1 d . . . H4A H 0.138(3) 0.6548(16) 0.6764(15) 0.021(4) Uiso 1 1 d . . . H14 H -0.204(3) 0.6029(15) 0.1804(15) 0.021(4) Uiso 1 1 d . . . H11 H 0.016(3) 1.0897(17) 0.1822(16) 0.027(4) Uiso 1 1 d . . . H12 H -0.054(3) 0.9415(15) 0.3071(15) 0.022(4) Uiso 1 1 d . . . H18 H 0.449(3) 0.5993(16) 0.3502(16) 0.023(4) Uiso 1 1 d . . . H5B H -0.198(3) 0.6827(16) 0.5381(15) 0.024(4) Uiso 1 1 d . . . H15 H -0.266(3) 0.3964(17) 0.0366(17) 0.029(4) Uiso 1 1 d . . . H9 H 0.555(3) 0.9552(16) 0.1234(16) 0.026(4) Uiso 1 1 d . . . H1 H 0.233(4) 1.162(2) 0.057(2) 0.051(6) Uiso 1 1 d . . . H2 H -0.094(4) 0.233(2) -0.028(2) 0.059(7) 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 0.0272(6) 0.0237(6) 0.0272(6) 0.0125(5) 0.0129(5) 0.0110(5) C1 0.0139(7) 0.0162(7) 0.0186(7) 0.0041(6) 0.0053(6) 0.0051(5) O2 0.0340(7) 0.0196(6) 0.0230(6) -0.0018(5) -0.0024(5) 0.0109(5) C11 0.0186(7) 0.0183(8) 0.0223(8) 0.0038(6) 0.0052(6) 0.0084(6) C7 0.0134(7) 0.0147(7) 0.0175(7) 0.0005(6) 0.0031(5) 0.0029(5) C2 0.0142(7) 0.0173(8) 0.0191(7) 0.0025(6) 0.0051(6) 0.0046(6) C17 0.0212(8) 0.0202(8) 0.0216(8) 0.0068(6) 0.0069(6) 0.0100(6) C12 0.0157(7) 0.0194(7) 0.0203(7) 0.0038(6) 0.0070(6) 0.0064(6) C15 0.0193(7) 0.0206(8) 0.0195(7) 0.0046(6) 0.0002(6) 0.0034(6) C10 0.0203(7) 0.0161(7) 0.0161(7) 0.0028(6) 0.0044(6) 0.0037(6) C8 0.0152(7) 0.0191(7) 0.0194(7) 0.0029(6) 0.0045(6) 0.0073(6) C14 0.0152(7) 0.0219(8) 0.0216(8) 0.0072(6) 0.0049(6) 0.0069(6) C13 0.0151(7) 0.0168(7) 0.0181(7) 0.0060(6) 0.0062(5) 0.0051(6) C9 0.0159(7) 0.0206(8) 0.0202(7) 0.0029(6) 0.0070(6) 0.0053(6) C6 0.0145(7) 0.0196(8) 0.0222(8) 0.0046(6) 0.0065(6) 0.0068(6) C5 0.0170(7) 0.0242(8) 0.0264(8) 0.0090(7) 0.0114(6) 0.0079(6) C16 0.0279(8) 0.0157(7) 0.0167(7) 0.0049(6) 0.0060(6) 0.0069(6) C18 0.0142(7) 0.0211(8) 0.0191(7) 0.0044(6) 0.0041(6) 0.0045(6) C3 0.0166(7) 0.0198(8) 0.0192(7) 0.0035(6) 0.0033(6) 0.0059(6) C4 0.0212(8) 0.0259(8) 0.0209(8) 0.0081(7) 0.0092(6) 0.0089(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C10 1.3645(17) . ? C1 C13 1.5398(19) . ? C1 C7 1.5398(19) . ? C1 C6 1.5461(19) . ? C1 C2 1.5512(19) . ? O2 C16 1.3745(17) . ? C11 C10 1.389(2) . ? C11 C12 1.392(2) . ? C7 C12 1.394(2) . ? C7 C8 1.3990(19) . ? C2 C3 1.525(2) . ? C17 C18 1.381(2) . ? C17 C16 1.385(2) . ? C15 C14 1.383(2) . ? C15 C16 1.385(2) . ? C10 C9 1.392(2) . ? C8 C9 1.384(2) . ? C14 C13 1.3988(19) . ? C13 C18 1.3983(19) . ? C6 C5 1.526(2) . ? C5 C4 1.524(2) . ? C3 C4 1.527(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C13 C1 C7 106.91(11) . . ? C13 C1 C6 110.87(11) . . ? C7 C1 C6 111.76(11) . . ? C13 C1 C2 112.78(11) . . ? C7 C1 C2 108.29(11) . . ? C6 C1 C2 106.28(11) . . ? C10 C11 C12 120.09(13) . . ? C12 C7 C8 116.85(13) . . ? C12 C7 C1 123.86(12) . . ? C8 C7 C1 119.29(12) . . ? C3 C2 C1 113.80(12) . . ? C18 C17 C16 119.80(13) . . ? C11 C12 C7 121.74(13) . . ? C14 C15 C16 119.60(13) . . ? O1 C10 C11 123.03(13) . . ? O1 C10 C9 117.66(13) . . ? C11 C10 C9 119.31(13) . . ? C9 C8 C7 122.23(13) . . ? C15 C14 C13 122.03(13) . . ? C18 C13 C14 116.72(13) . . ? C18 C13 C1 122.58(12) . . ? C14 C13 C1 120.57(12) . . ? C8 C9 C10 119.77(13) . . ? C5 C6 C1 112.32(12) . . ? C4 C5 C6 111.27(12) . . ? O2 C16 C17 117.10(13) . . ? O2 C16 C15 122.99(13) . . ? C17 C16 C15 119.91(13) . . ? C17 C18 C13 121.93(13) . . ? C2 C3 C4 111.10(12) . . ? C5 C4 C3 110.50(12) . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 26.09 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.334 _refine_diff_density_min -0.226 _refine_diff_density_rms 0.047