data_global _journal_coden_Cambridge 182 _publ_contact_author_name 'Prof. Ashwini Nangia' _publ_contact_author_address ; School of Chemistry University of Hyderabad Hyderabad 500 046 India ; _publ_contact_author_email ashwini_nangia@rediffmail.com _publ_contact_author_phone '91 40 23011338' _publ_contact_author_fax '91 40 23011338' loop_ _publ_author_name _publ_author_address 'Aitipamula Srinivasulu' ; School of Chemistry University of Hyderabad Hyderabad 500 046 India ; 'Ashwini Nangia' ; School of Chemistry University of Hyderabad Hyderabad 500 046 India ; _publ_requested_journal 'Chemical Communications' _publ_section_title ; Concomitant polymorphs of 2,2',6,6'-tetramethyl-4,4'-terphenyldiol: the b-quinol network reproduced in a metastable polymorph ; data_compound2 _database_code_depnum_ccdc_archive 'CCDC 261093' _audit_creation_method SHELXL-97 _chemical_name_systematic ; DMSO solvate of 4,4'-terphenyldiol (1:1) ; _chemical_name_common ? _chemical_melting_point 518 _chemical_formula_moiety 'C18 H14 O2, C2 H6 O S' _chemical_formula_sum 'C20 H20 O3 S' _chemical_formula_weight 340.42 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pnma loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z' 'x+1/2, -y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z' '-x-1/2, y-1/2, z-1/2' _cell_length_a 7.1305(14) _cell_length_b 34.505(7) _cell_length_c 6.8846(14) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1693.9(6) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.335 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 720 _exptl_absorpt_coefficient_mu 0.206 _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 '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 10026 _diffrn_reflns_av_R_equivalents 0.0778 _diffrn_reflns_av_sigmaI/netI 0.0432 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -46 _diffrn_reflns_limit_k_max 45 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 3.45 _diffrn_reflns_theta_max 29.29 _reflns_number_total 2204 _reflns_number_gt 1883 _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 X-Seed _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^)+(0.1035P)^2^+1.8885P] 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 2204 _refine_ls_number_parameters 152 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0714 _refine_ls_R_factor_gt 0.0577 _refine_ls_wR_factor_ref 0.1707 _refine_ls_wR_factor_gt 0.1465 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.048 _refine_ls_shift/su_max 0.011 _refine_ls_shift/su_mean 0.001 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 S1 S 0.67323(9) 0.7500 0.02666(9) 0.0110(2) Uani 1 2 d S . . O1 O 0.84145(19) 0.69319(4) 0.4780(2) 0.0127(3) Uani 1 1 d . . . H1 H 0.781(5) 0.7082(10) 0.390(5) 0.037(8) Uiso 1 1 d . . . O2 O 0.6854(3) 0.7500 0.2480(3) 0.0152(4) Uani 1 2 d S . . C1 C 0.7698(3) 0.65626(5) 0.4796(2) 0.0110(4) Uani 1 1 d . . . C2 C 0.8442(3) 0.63019(5) 0.6137(3) 0.0121(4) Uani 1 1 d . . . H2A H 0.937(3) 0.6401(7) 0.705(3) 0.012(5) Uiso 1 1 d . . . C3 C 0.7775(3) 0.59214(5) 0.6188(3) 0.0129(4) Uani 1 1 d . . . H3A H 0.826(3) 0.5751(7) 0.713(4) 0.018(6) Uiso 1 1 d . . . C4 C 0.6377(3) 0.57940(5) 0.4916(2) 0.0107(4) Uani 1 1 d . . . C5 C 0.5659(3) 0.60614(5) 0.3577(2) 0.0110(4) Uani 1 1 d . . . H5A H 0.477(4) 0.5978(7) 0.263(3) 0.010(5) Uiso 1 1 d . . . C6 C 0.6308(3) 0.64417(5) 0.3514(3) 0.0116(4) Uani 1 1 d . . . H6A H 0.579(3) 0.6621(7) 0.257(3) 0.011(6) Uiso 1 1 d . . . C7 C 0.5671(3) 0.53876(5) 0.4962(2) 0.0108(4) Uani 1 1 d . . . C8 C 0.6810(3) 0.50826(5) 0.5613(3) 0.0126(4) Uani 1 1 d . . . H8A H 0.811(4) 0.5141(8) 0.598(4) 0.020(6) Uiso 1 1 d . . . C9 C 0.6144(3) 0.47027(5) 0.5653(3) 0.0135(4) Uani 1 1 d . . . H9A H 0.701(4) 0.4496(9) 0.609(4) 0.029(7) Uiso 1 1 d . . . C10 C 0.8209(3) 0.71118(6) -0.0506(3) 0.0180(4) Uani 1 1 d . . . H10A H 0.767(5) 0.6875(9) -0.010(4) 0.034(8) Uiso 1 1 d . . . H10B H 0.823(4) 0.7128(9) -0.181(5) 0.036(8) Uiso 1 1 d . . . H10C H 0.947(4) 0.7162(8) 0.000(4) 0.019(6) 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 S1 0.0126(3) 0.0088(3) 0.0115(3) 0.000 -0.0009(2) 0.000 O1 0.0164(7) 0.0071(7) 0.0147(7) 0.0011(5) -0.0011(5) -0.0027(5) O2 0.0224(10) 0.0125(9) 0.0106(8) 0.000 0.0025(7) 0.000 C1 0.0131(8) 0.0082(8) 0.0118(8) -0.0003(6) 0.0024(6) -0.0006(6) C2 0.0132(8) 0.0121(9) 0.0111(8) -0.0007(6) -0.0018(6) -0.0011(6) C3 0.0166(9) 0.0113(9) 0.0110(8) 0.0022(6) -0.0020(7) -0.0004(7) C4 0.0117(8) 0.0101(9) 0.0103(7) 0.0013(6) 0.0014(6) 0.0004(6) C5 0.0125(8) 0.0099(8) 0.0107(8) 0.0001(6) -0.0018(6) -0.0011(6) C6 0.0128(8) 0.0102(8) 0.0118(8) 0.0025(6) 0.0001(6) 0.0008(7) C7 0.0149(8) 0.0089(9) 0.0085(7) 0.0012(6) 0.0007(6) -0.0020(7) C8 0.0141(9) 0.0108(9) 0.0129(8) 0.0018(6) -0.0033(6) -0.0012(6) C9 0.0155(9) 0.0116(9) 0.0135(8) 0.0010(6) -0.0028(7) -0.0007(7) C10 0.0269(11) 0.0132(9) 0.0139(9) -0.0015(7) 0.0025(7) 0.0071(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 S1 O2 1.526(2) . ? S1 C10 1.785(2) . ? S1 C10 1.785(2) 7_575 ? O1 C1 1.373(2) . ? O1 H1 0.91(3) . ? C1 C6 1.392(3) . ? C1 C2 1.393(3) . ? C2 C3 1.397(3) . ? C2 H2A 0.98(2) . ? C3 C4 1.397(3) . ? C3 H3A 0.94(3) . ? C4 C5 1.401(2) . ? C4 C7 1.490(3) . ? C5 C6 1.392(2) . ? C5 H5A 0.96(2) . ? C6 H6A 0.97(2) . ? C7 C9 1.397(3) 5_666 ? C7 C8 1.403(3) . ? C8 C9 1.394(3) . ? C8 H8A 0.98(3) . ? C9 C7 1.397(3) 5_666 ? C9 H9A 0.99(3) . ? C10 H10A 0.95(3) . ? C10 H10B 0.90(3) . ? C10 H10C 0.98(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 S1 C10 105.31(9) . . ? O2 S1 C10 105.31(9) . 7_575 ? C10 S1 C10 97.27(16) . 7_575 ? C1 O1 H1 111(2) . . ? O1 C1 C6 122.54(16) . . ? O1 C1 C2 117.60(16) . . ? C6 C1 C2 119.85(17) . . ? C1 C2 C3 119.60(17) . . ? C1 C2 H2A 117.3(14) . . ? C3 C2 H2A 123.0(14) . . ? C2 C3 C4 121.52(17) . . ? C2 C3 H3A 118.6(16) . . ? C4 C3 H3A 119.8(15) . . ? C3 C4 C5 117.74(17) . . ? C3 C4 C7 121.59(16) . . ? C5 C4 C7 120.66(16) . . ? C6 C5 C4 121.33(17) . . ? C6 C5 H5A 118.9(14) . . ? C4 C5 H5A 119.6(14) . . ? C1 C6 C5 119.95(16) . . ? C1 C6 H6A 120.2(14) . . ? C5 C6 H6A 119.8(14) . . ? C9 C7 C8 117.75(17) 5_666 . ? C9 C7 C4 121.11(17) 5_666 . ? C8 C7 C4 121.14(16) . . ? C9 C8 C7 120.98(17) . . ? C9 C8 H8A 120.6(16) . . ? C7 C8 H8A 118.4(16) . . ? C8 C9 C7 121.27(17) . 5_666 ? C8 C9 H9A 118.3(18) . . ? C7 C9 H9A 120.4(17) 5_666 . ? S1 C10 H10A 109(2) . . ? S1 C10 H10B 105(2) . . ? H10A C10 H10B 111(3) . . ? S1 C10 H10C 107.7(16) . . ? H10A C10 H10C 115(3) . . ? H10B C10 H10C 109(3) . . ? _diffrn_measured_fraction_theta_max 0.937 _diffrn_reflns_theta_full 29.29 _diffrn_measured_fraction_theta_full 0.937 _refine_diff_density_max 0.653 _refine_diff_density_min -0.602 _refine_diff_density_rms 0.108 data_1a _database_code_depnum_ccdc_archive 'CCDC 261094' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Form 1 of 2,2',6,6'-tetramethyl- 4,4'-terphenyldiol (1a) ; _chemical_name_common ? _chemical_melting_point 531 _chemical_formula_moiety 'C22 H22 O2' _chemical_formula_sum 'C22 H22 O2' _chemical_formula_weight 318.40 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 hexagonal _symmetry_space_group_name_H-M R-3 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' '-x+2/3, -y+1/3, -z+1/3' 'y+2/3, -x+y+1/3, -z+1/3' 'x-y+2/3, x+1/3, -z+1/3' '-x+1/3, -y+2/3, -z+2/3' 'y+1/3, -x+y+2/3, -z+2/3' 'x-y+1/3, x+2/3, -z+2/3' _cell_length_a 20.8580(12) _cell_length_b 20.8580(12) _cell_length_c 10.0116(12) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 3772.1(5) _cell_formula_units_Z 9 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2990 _cell_measurement_theta_min 2.33 _cell_measurement_theta_max 28.15 _exptl_crystal_description Hexagonal _exptl_crystal_colour 'Dark pink' _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.261 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1530 _exptl_absorpt_coefficient_mu 0.079 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9813 _exptl_absorpt_correction_T_max 0.9859 _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 9370 _diffrn_reflns_av_R_equivalents 0.0329 _diffrn_reflns_av_sigmaI/netI 0.0246 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 24 _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 1.95 _diffrn_reflns_theta_max 26.35 _reflns_number_total 1720 _reflns_number_gt 1514 _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 X-Seed _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^)+(0.0463P)^2^+4.8519P] 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 1720 _refine_ls_number_parameters 115 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0456 _refine_ls_R_factor_gt 0.0392 _refine_ls_wR_factor_ref 0.0994 _refine_ls_wR_factor_gt 0.0953 _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_restrained_S_all 1.029 _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 0.19252(5) 0.60016(5) 1.11504(9) 0.0188(2) Uani 1 1 d . . . C1 C 0.05882(7) 0.49069(7) 0.85922(13) 0.0172(3) Uani 1 1 d . . . H1 H 0.0184 0.4418 0.8483 0.021 Uiso 1 1 calc R . . C2 C 0.07879(7) 0.54049(7) 0.75302(13) 0.0169(3) Uani 1 1 d . . . C3 C 0.17880(7) 0.63366(7) 0.88948(13) 0.0165(3) Uani 1 1 d . . . C4 C 0.15570(7) 0.58245(7) 0.99390(12) 0.0157(3) Uani 1 1 d . . . C5 C 0.09636(7) 0.51043(7) 0.98046(13) 0.0167(3) Uani 1 1 d . . . C6 C 0.13899(7) 0.61151(7) 0.77059(12) 0.0167(3) Uani 1 1 d . . . H6 H 0.1533 0.6459 0.6991 0.020 Uiso 1 1 calc R . . C7 C 0.24561(8) 0.70959(8) 0.90305(13) 0.0219(3) Uani 1 1 d . . . H7A H 0.2615 0.7319 0.8144 0.033 Uiso 1 1 calc R . . H7B H 0.2858 0.7057 0.9457 0.033 Uiso 1 1 calc R . . H7C H 0.2330 0.7406 0.9579 0.033 Uiso 1 1 calc R . . C8 C 0.02718(7) 0.57018(7) 0.55126(13) 0.0191(3) Uani 1 1 d . . . H8 H 0.0455 0.6187 0.5856 0.023 Uiso 1 1 calc R . . C9 C -0.00952(7) 0.55152(7) 0.42979(13) 0.0189(3) Uani 1 1 d . . . H9 H -0.0156 0.5876 0.3824 0.023 Uiso 1 1 calc R . . C10 C 0.03779(7) 0.51919(7) 0.62438(13) 0.0169(3) Uani 1 1 d . . . C11 C 0.07451(8) 0.45659(7) 1.09460(13) 0.0209(3) Uani 1 1 d . . . H11A H 0.0263 0.4129 1.0756 0.031 Uiso 1 1 calc R . . H11B H 0.0712 0.4803 1.1768 0.031 Uiso 1 1 calc R . . H11C H 0.1118 0.4415 1.1058 0.031 Uiso 1 1 calc R . . H11 H 0.2167(11) 0.6467(12) 1.1316(19) 0.045(6) 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 0.0241(5) 0.0180(5) 0.0139(5) -0.0015(4) -0.0049(4) 0.0102(4) C1 0.0160(6) 0.0159(6) 0.0191(7) -0.0019(5) -0.0013(5) 0.0075(5) C2 0.0174(6) 0.0200(7) 0.0157(6) -0.0016(5) -0.0007(5) 0.0112(5) C3 0.0173(6) 0.0182(6) 0.0162(7) -0.0016(5) -0.0003(5) 0.0105(5) C4 0.0178(6) 0.0208(7) 0.0126(6) -0.0029(5) -0.0014(5) 0.0128(5) C5 0.0176(6) 0.0199(7) 0.0161(6) 0.0003(5) 0.0016(5) 0.0119(5) C6 0.0194(6) 0.0185(6) 0.0137(6) 0.0013(5) 0.0008(5) 0.0107(5) C7 0.0246(7) 0.0205(7) 0.0161(7) 0.0004(5) -0.0036(5) 0.0080(6) C8 0.0201(7) 0.0172(6) 0.0183(7) -0.0035(5) -0.0029(5) 0.0081(5) C9 0.0204(7) 0.0188(7) 0.0184(7) 0.0019(5) -0.0016(5) 0.0103(5) C10 0.0145(6) 0.0193(7) 0.0154(6) -0.0003(5) -0.0001(5) 0.0074(5) C11 0.0222(7) 0.0194(7) 0.0193(7) 0.0010(5) -0.0014(5) 0.0091(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 C4 1.3832(15) . ? O1 H11 0.86(2) . ? C1 C5 1.3905(18) . ? C1 C2 1.3966(18) . ? C1 H1 0.9500 . ? C2 C6 1.3935(18) . ? C2 C10 1.4858(17) . ? C3 C6 1.3915(18) . ? C3 C4 1.3968(18) . ? C3 C7 1.5038(18) . ? C4 C5 1.3954(18) . ? C5 C11 1.5044(18) . ? C6 H6 0.9500 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 C9 1.3851(18) . ? C8 C10 1.3968(18) . ? C8 H8 0.9500 . ? C9 C10 1.3956(18) 10_566 ? C9 H9 0.9500 . ? C10 C9 1.3956(18) 10_566 ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? 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 C4 O1 H11 113.9(13) . . ? C5 C1 C2 122.00(12) . . ? C5 C1 H1 119.0 . . ? C2 C1 H1 119.0 . . ? C6 C2 C1 118.01(11) . . ? C6 C2 C10 120.35(11) . . ? C1 C2 C10 121.64(11) . . ? C6 C3 C4 117.77(12) . . ? C6 C3 C7 120.79(12) . . ? C4 C3 C7 121.42(11) . . ? O1 C4 C5 116.56(11) . . ? O1 C4 C3 121.25(11) . . ? C5 C4 C3 122.15(11) . . ? C1 C5 C4 117.91(12) . . ? C1 C5 C11 121.77(12) . . ? C4 C5 C11 120.33(11) . . ? C3 C6 C2 122.13(12) . . ? C3 C6 H6 118.9 . . ? C2 C6 H6 118.9 . . ? C3 C7 H7A 109.5 . . ? C3 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C3 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C9 C8 C10 121.46(12) . . ? C9 C8 H8 119.3 . . ? C10 C8 H8 119.3 . . ? C8 C9 C10 121.35(12) . 10_566 ? C8 C9 H9 119.3 . . ? C10 C9 H9 119.3 10_566 . ? C9 C10 C8 117.19(12) 10_566 . ? C9 C10 C2 121.91(12) 10_566 . ? C8 C10 C2 120.88(12) . . ? C5 C11 H11A 109.5 . . ? C5 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C5 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 26.35 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.271 _refine_diff_density_min -0.168 _refine_diff_density_rms 0.042 data_1b _database_code_depnum_ccdc_archive 'CCDC 261095' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Form 2 of 2,2',6,6'-tetramethyl- 4,4'-terphenyldiol (1b) ; _chemical_name_common ? _chemical_melting_point 531 _chemical_formula_moiety 'C22 H22 O2' _chemical_formula_sum 'C22 H22 O2' _chemical_formula_weight 318.40 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 P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.553(2) _cell_length_b 4.5252(11) _cell_length_c 20.210(5) _cell_angle_alpha 90.00 _cell_angle_beta 100.555(3) _cell_angle_gamma 90.00 _cell_volume 858.9(4) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 1071 _cell_measurement_theta_min 2.70 _cell_measurement_theta_max 26.57 _exptl_crystal_description needle _exptl_crystal_colour pink _exptl_crystal_size_max 0.39 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.231 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 340 _exptl_absorpt_coefficient_mu 0.077 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9705 _exptl_absorpt_correction_T_max 0.9938 _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 5033 _diffrn_reflns_av_R_equivalents 0.0301 _diffrn_reflns_av_sigmaI/netI 0.0355 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.05 _diffrn_reflns_theta_max 26.41 _reflns_number_total 1762 _reflns_number_gt 1393 _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 X-Seed _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^)+(0.0473P)^2^+0.7004P] 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 1762 _refine_ls_number_parameters 137 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0804 _refine_ls_R_factor_gt 0.0632 _refine_ls_wR_factor_ref 0.1415 _refine_ls_wR_factor_gt 0.1322 _refine_ls_goodness_of_fit_ref 1.066 _refine_ls_restrained_S_all 1.066 _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 0.07738(14) 0.6500(3) 0.24211(7) 0.0246(4) Uani 1 1 d . . . C1 C 0.1591(2) 0.7063(4) 0.19331(10) 0.0243(5) Uani 1 1 d . . . C2 C 0.1249(2) 0.5858(5) 0.12892(10) 0.0276(5) Uani 1 1 d . . . C3 C 0.2740(2) 0.8969(5) 0.21197(11) 0.0284(5) Uani 1 1 d . . . C4 C 0.3554(2) 0.9684(5) 0.16393(12) 0.0355(6) Uani 1 1 d . . . H3 H 0.4332 1.1005 0.1756 0.043 Uiso 1 1 calc R . . C5 C 0.2110(2) 0.6602(5) 0.08300(11) 0.0343(6) Uani 1 1 d . . . H2 H 0.1906 0.5774 0.0391 0.041 Uiso 1 1 calc R . . C6 C 0.3262(2) 0.8520(5) 0.09906(12) 0.0365(6) Uani 1 1 d . . . C7 C -0.0010(2) 0.3857(5) 0.10903(11) 0.0325(5) Uani 1 1 d . . . H7A H -0.0015 0.3078 0.0637 0.049 Uiso 1 1 calc R . . H7B H -0.0889 0.4971 0.1093 0.049 Uiso 1 1 calc R . . H7C H 0.0051 0.2214 0.1410 0.049 Uiso 1 1 calc R . . C8 C 0.3084(2) 1.0234(5) 0.28181(11) 0.0357(6) Uani 1 1 d . . . H8A H 0.4035 1.1124 0.2890 0.054 Uiso 1 1 calc R . . H8B H 0.3062 0.8656 0.3148 0.054 Uiso 1 1 calc R . . H8C H 0.2379 1.1747 0.2871 0.054 Uiso 1 1 calc R . . C9 C 0.4158(2) 0.9278(6) 0.04816(13) 0.0456(7) Uani 1 1 d . . . C10 C 0.5624(4) 0.9607(12) 0.0665(2) 0.0710(16) Uani 0.69 1 d P . 1 H4 H 0.6066 0.9360 0.1122 0.058(12) Uiso 0.69 1 calc PR . 1 C13 C 0.3550(4) 0.9711(12) -0.0191(2) 0.0718(16) Uani 0.69 1 d P . 1 H6 H 0.2548 0.9536 -0.0327 0.055(11) Uiso 0.69 1 calc PR . 1 C11 C 0.4416(6) 0.7203(13) 0.0004(3) 0.0169(12) Uani 0.31 1 d P . 2 H5 H 0.4022 0.5275 0.0004 0.018(16) Uiso 0.31 1 calc PR . 2 C12 C 0.4758(6) 1.2060(13) 0.0471(3) 0.0181(12) Uani 0.31 1 d P . 2 H7 H 0.4602 1.3490 0.0793 0.010(14) Uiso 0.31 1 calc PR . 2 H1 H 0.026(3) 0.476(7) 0.2337(14) 0.062(9) 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 0.0242(7) 0.0245(8) 0.0288(8) 0.0029(6) 0.0147(6) -0.0004(6) C1 0.0202(10) 0.0239(10) 0.0322(11) 0.0124(9) 0.0137(8) 0.0089(8) C2 0.0260(10) 0.0307(11) 0.0289(11) 0.0095(9) 0.0123(9) 0.0111(9) C3 0.0194(10) 0.0301(12) 0.0376(12) 0.0119(9) 0.0106(9) 0.0056(8) C4 0.0200(10) 0.0407(13) 0.0480(14) 0.0214(11) 0.0119(10) 0.0055(9) C5 0.0306(11) 0.0463(14) 0.0295(12) 0.0139(10) 0.0150(9) 0.0138(10) C6 0.0246(11) 0.0496(14) 0.0404(13) 0.0265(11) 0.0190(10) 0.0153(10) C7 0.0383(12) 0.0364(13) 0.0256(11) 0.0019(9) 0.0135(9) 0.0017(10) C8 0.0258(11) 0.0369(13) 0.0462(14) 0.0036(11) 0.0112(10) -0.0033(9) C9 0.0279(12) 0.0660(18) 0.0484(15) 0.0377(13) 0.0214(11) 0.0166(11) C10 0.035(2) 0.120(4) 0.066(3) 0.066(3) 0.0288(19) 0.032(2) C13 0.0299(19) 0.116(4) 0.077(3) 0.068(3) 0.0285(19) 0.031(2) C11 0.023(3) 0.016(3) 0.015(3) -0.001(2) 0.012(2) -0.001(2) C12 0.024(3) 0.015(3) 0.019(3) -0.002(2) 0.012(2) 0.000(2) _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 1.389(2) . ? O1 H1 0.93(3) . ? C1 C3 1.392(3) . ? C1 C2 1.394(3) . ? C2 C5 1.389(3) . ? C2 C7 1.501(3) . ? C3 C4 1.389(3) . ? C3 C8 1.503(3) . ? C4 C6 1.393(3) . ? C4 H3 0.9500 . ? C5 C6 1.392(3) . ? C5 H2 0.9500 . ? C6 C9 1.493(3) . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 C12 1.385(6) . ? C9 C10 1.390(5) . ? C9 C13 1.390(5) . ? C9 C11 1.401(6) . ? C10 C13 1.382(5) 3_675 ? C10 H4 0.9500 . ? C13 C10 1.382(5) 3_675 ? C13 H6 0.9500 . ? C11 C12 1.390(7) 3_675 ? C11 H5 0.9500 . ? C12 C11 1.390(7) 3_675 ? C12 H7 0.9500 . ? 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 C1 O1 H1 111.9(17) . . ? O1 C1 C3 116.04(19) . . ? O1 C1 C2 121.69(18) . . ? C3 C1 C2 122.24(18) . . ? C5 C2 C1 117.6(2) . . ? C5 C2 C7 120.7(2) . . ? C1 C2 C7 121.70(17) . . ? C4 C3 C1 118.0(2) . . ? C4 C3 C8 120.9(2) . . ? C1 C3 C8 121.07(18) . . ? C3 C4 C6 121.9(2) . . ? C3 C4 H3 119.0 . . ? C6 C4 H3 119.0 . . ? C2 C5 C6 122.3(2) . . ? C2 C5 H2 118.8 . . ? C6 C5 H2 118.8 . . ? C5 C6 C4 117.92(19) . . ? C5 C6 C9 120.7(2) . . ? C4 C6 C9 121.4(2) . . ? C2 C7 H7A 109.5 . . ? C2 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C2 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C3 C8 H8A 109.5 . . ? C3 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C3 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C12 C9 C10 60.5(3) . . ? C12 C9 C13 87.5(4) . . ? C10 C9 C13 117.7(3) . . ? C12 C9 C11 118.2(4) . . ? C10 C9 C11 87.7(4) . . ? C13 C9 C11 61.0(3) . . ? C12 C9 C6 120.7(3) . . ? C10 C9 C6 121.2(3) . . ? C13 C9 C6 121.1(2) . . ? C11 C9 C6 121.1(3) . . ? C13 C10 C9 121.0(4) 3_675 . ? C13 C10 H4 119.5 3_675 . ? C9 C10 H4 119.5 . . ? C10 C13 C9 121.3(4) 3_675 . ? C10 C13 H6 119.3 3_675 . ? C9 C13 H6 119.3 . . ? C12 C11 C9 120.6(5) 3_675 . ? C12 C11 H5 119.7 3_675 . ? C9 C11 H5 119.7 . . ? C9 C12 C11 121.2(5) . 3_675 ? C9 C12 H7 119.4 . . ? C11 C12 H7 119.4 3_675 . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.41 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.264 _refine_diff_density_min -0.270 _refine_diff_density_rms 0.046