#------------------------------------------------------------------------------ #$Date: 2025-08-19 07:12:48 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301798 $ #$URL: svn://www.crystallography.net/cod/cif/2/01/10/2011001.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2011001 loop_ _publ_author_name 'Gerkin, Roger E.' _publ_section_title ; Hydrogen bonds and C---H···O interactions in 2,2'-dimethoxybiphenyl-5,5'-dimethanol at 150K ; _journal_issue 6 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 677 _journal_page_last 678 _journal_paper_doi 10.1107/S0108270100002900 _journal_volume 56 _journal_year 2000 _chemical_formula_moiety 'C16 H18 O4' _chemical_formula_sum 'C16 H18 O4' _chemical_formula_weight 274.32 _chemical_name_common 2,2'-dimethoxybiphenyl-5,5'-dimethanol _chemical_name_systematic 2,2'-dimethoxybiphenyl-5,5'-dimethanol _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _cell_angle_alpha 90 _cell_angle_beta 107.4730(10) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 11.4104(2) _cell_length_b 7.40780(10) _cell_length_c 16.9198(3) _cell_measurement_reflns_used 26987 _cell_measurement_temperature 150 _cell_measurement_theta_max 27.48 _cell_measurement_theta_min 1.91 _cell_volume 1364.17(4) _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_collection 'COLLECT (Nonius, 1999)' _computing_data_reduction DENZO-SMN _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material 'TEXSAN and PLATON (Spek, 1990)' _computing_structure_refinement 'TEXSAN (Molecular Structure Corporation, 1992-1997)' _computing_structure_solution 'SHELXS86 (Sheldrick, 1990)' _diffrn_ambient_temperature 150 _diffrn_measured_fraction_theta_max .999 _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method '\w scans with \k offsets' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'X-ray tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength .71073 _diffrn_reflns_av_R_equivalents .042 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_number 27579 _diffrn_reflns_theta_max 27.50 _exptl_absorpt_coefficient_mu .095 _exptl_absorpt_correction_type none _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.336 _exptl_crystal_density_meas ? _exptl_crystal_description 'cut column' _exptl_crystal_F_000 584 _exptl_crystal_size_max .27 _exptl_crystal_size_mid .23 _exptl_crystal_size_min .19 _refine_diff_density_max .28 _refine_diff_density_min -.31 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.99 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 189 _refine_ls_number_reflns 3137 _refine_ls_R_factor_gt .046 _refine_ls_shift/su_max <0.001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^~cs~ + (0.026I)^2^]' _refine_ls_weighting_scheme sigma _refine_ls_wR_factor_ref .099 _reflns_number_gt 2471 _reflns_number_total 3137 _reflns_threshold_expression I>2\s(I) _cod_data_source_file fr1262.cif _cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_exptl_crystal_density_meas' value 'not measured' was changed to '?' - the value is perceived as not measured. Automatic conversion script Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas ; _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 2011001 _cod_database_fobs_code 2011001 loop_ _symmetry_equiv_pos_as_xyz ' +x, +y, +z' ' -x,1/2+y,1/2-z' ' -x, -y, -z' ' +x,1/2-y,1/2+z' loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_calc_attached_atom _atom_site_refinement_flags _atom_site_occupancy O1 .30374(7) .21760(10) .84047(5) .0258(2) Uani d ? . 1.000 O2 -.05028(9) -.32990(10) .93253(6) .0366(3) Uani d ? . 1.000 O3 .43676(7) -.14310(10) .89559(5) .0294(3) Uani d ? . 1.000 O4 .18529(9) -.07920(10) .51018(5) .0313(3) Uani d ? . 1.000 C1 .19210(10) -.0542(2) .81556(7) .0197(3) Uani d ? . 1.000 C2 .20810(10) .1183(2) .85151(7) .0203(3) Uani d ? . 1.000 C3 .12960(10) .1828(2) .89336(8) .0241(3) Uani d ? . 1.000 C4 .03150(10) .0765(2) .89818(7) .0236(3) Uani d ? . 1.000 C5 .00910(10) -.0905(2) .86006(7) .0227(3) Uani d ? . 1.000 C6 .09080(10) -.1545(2) .81941(7) .0216(3) Uani d ? . 1.000 C7 .27650(10) -.1248(2) .77038(7) .0203(3) Uani d ? . 1.000 C8 .39960(10) -.1691(2) .81157(8) .0223(3) Uani d ? . 1.000 C9 .47400(10) -.2376(2) .76727(8) .0257(3) Uani d ? . 1.000 C10 .42800(10) -.2574(2) .68193(8) .0251(4) Uani d ? . 1.000 C11 .30780(10) -.2131(2) .63939(7) .0229(3) Uani d ? . 1.000 C12 .23290(10) -.1495(2) .68524(7) .0211(3) Uani d ? . 1.000 C13 .29990(10) .4082(2) .85129(9) .0343(4) Uani d ? . 1.000 C14 -.09630(10) -.2047(2) .86661(8) .0279(4) Uani d ? . 1.000 C15 .56080(10) -.1891(2) .94011(9) .0382(4) Uani d ? . 1.000 C16 .25910(10) -.2318(2) .54662(8) .0282(4) Uani d ? . 1.000 H1O2 -.109(2) -.405(3) .9370(10) .070(6) Uiso d ? . 1.000 H1O4 .108(2) -.124(2) .4800(10) .071(6) Uiso d ? . 1.000 H3 .1429 .3023 .9194 .029 Uiso c C3 . 1.000 H4 -.0228 .1207 .9292 .028 Uiso c C4 . 1.000 H6 .0763 -.2733 .7928 .026 Uiso c C6 . 1.000 H9 .5590 -.2720 .7962 .031 Uiso c C9 . 1.000 H10 .4818 -.3038 .6511 .030 Uiso c C10 . 1.000 H12 .1467 -.1215 .6563 .025 Uiso c C12 . 1.000 H13C .3127 .4355 .9099 .041 Uiso c C13 . 1.000 H13A .3648 .4655 .8330 .041 Uiso c C13 . 1.000 H13B .2197 .4546 .8183 .041 Uiso c C13 . 1.000 H14A -.1322 -.2699 .8146 .034 Uiso c C14 . 1.000 H14B -.1591 -.1281 .8783 .034 Uiso c C14 . 1.000 H15B .6171 -.1223 .9171 .046 Uiso c C15 . 1.000 H15C .5772 -.1576 .9987 .046 Uiso c C15 . 1.000 H15A .5732 -.3190 .9351 .046 Uiso c C15 . 1.000 H16A .3284 -.2412 .5239 .034 Uiso c C16 . 1.000 H16B .2090 -.3414 .5331 .034 Uiso c C16 . 1.000 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O1 .0250(5) .0190(5) .0381(5) -.0032(4) .0165(4) -.0014(4) O2 .0368(6) .0409(6) .0312(6) -.0157(5) .0090(4) .0072(4) O3 .0243(5) .0364(5) .0254(5) .0045(4) .0042(4) .0011(4) O4 .0373(6) .0288(5) .0297(5) .0091(4) .0128(4) .0015(4) C1 .0199(6) .0212(6) .0182(6) .0025(5) .0061(5) .0027(5) C2 .0186(6) .0206(7) .0219(6) -.0018(5) .0063(5) .0031(5) C3 .0262(7) .0216(7) .0257(7) -.0006(5) .0097(5) -.0014(5) C4 .0233(6) .0263(7) .0235(7) .0022(5) .0106(5) .0014(5) C5 .0207(6) .0249(7) .0223(7) .0002(5) .0062(5) .0033(5) C6 .0229(6) .0195(6) .0227(7) -.0008(5) .0073(5) -.0003(5) C7 .0212(6) .0160(6) .0264(7) -.0010(5) .0112(5) .0015(5) C8 .0234(7) .0182(6) .0258(7) -.0022(5) .0080(5) .0008(5) C9 .0191(6) .0240(7) .0339(8) .0015(5) .0078(5) .0014(6) C10 .0242(7) .0210(7) .0345(8) .0005(5) .0154(6) -.0015(6) C11 .0251(7) .0183(6) .0282(7) -.0007(5) .0125(6) -.0006(5) C12 .0192(6) .0180(6) .0269(7) .0003(5) .0083(5) .0005(5) C13 .0368(8) .0190(7) .0533(9) -.0036(6) .0228(7) .0007(6) C14 .0249(7) .0302(7) .0316(8) -.0035(6) .0128(6) .0002(6) C15 .0287(7) .0448(9) .0351(8) .0069(6) .0006(6) .0019(7) C16 .0282(7) .0281(7) .0314(8) .0065(6) .0138(6) -.0010(6) loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source H 0 0 'Stewart et al. (1965)' C .003 .002 'Creagh & McAuley (1992)' O .011 .006 'Creagh & McAuley (1992)' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag C2 O1 C13 117.17(9) yes C14 O2 H1O2 111.0(10) no C8 O3 C15 117.50(10) yes C16 O4 H1O4 107.0(10) no C2 C1 C6 117.90(10) no C2 C1 C7 121.40(10) no C6 C1 C7 120.70(10) no O1 C2 C1 115.70(10) yes O1 C2 C3 123.20(10) yes C1 C2 C3 121.10(10) no C2 C3 C4 119.40(10) no C2 C3 H3 120.3 no C4 C3 H3 120.3 no C3 C4 C5 121.20(10) no C3 C4 H4 119.4 no C5 C4 H4 119.4 no C4 C5 C6 118.50(10) no C4 C5 C14 120.60(10) no C6 C5 C14 120.90(10) no C1 C6 C5 121.90(10) no C1 C6 H6 119.0 no C5 C6 H6 119.1 no C1 C7 C8 122.00(10) no C1 C7 C12 119.50(10) no C8 C7 C12 118.50(10) no O3 C8 C7 115.70(10) yes O3 C8 C9 124.30(10) yes C7 C8 C9 120.00(10) no C8 C9 C10 119.90(10) no C8 C9 H9 120.0 no C10 C9 H9 120.0 no C9 C10 C11 121.50(10) no C9 C10 H10 119.2 no C11 C10 H10 119.2 no C10 C11 C12 117.90(10) no C10 C11 C16 121.20(10) no C12 C11 C16 120.90(10) no C7 C12 C11 122.20(10) no C7 C12 H12 118.9 no C11 C12 H12 118.9 no O1 C13 H13C 109.5 no O1 C13 H13A 109.5 no O1 C13 H13B 109.5 no H13C C13 H13A 109.5 no H13C C13 H13B 109.5 no H13A C13 H13B 109.5 no O2 C14 C5 108.00(10) yes O2 C14 H14A 109.8 no O2 C14 H14B 109.8 no C5 C14 H14A 109.8 no C5 C14 H14B 109.8 no H14A C14 H14B 109.5 no O3 C15 H15B 109.5 no O3 C15 H15C 109.5 no O3 C15 H15A 109.5 no H15B C15 H15C 109.5 no H15B C15 H15A 109.5 no H15C C15 H15A 109.5 no O4 C16 C11 111.20(10) yes O4 C16 H16A 109.0 no O4 C16 H16B 109.0 no C11 C16 H16A 109.1 no C11 C16 H16B 109.0 no H16A C16 H16B 109.5 no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 C2 . . 1.3740(10) yes O1 C13 . . 1.426(2) yes O2 C14 . . 1.424(2) yes O2 H1O2 . . .89(2) no O3 C8 . . 1.3700(10) yes O3 C15 . . 1.431(2) yes O4 C16 . . 1.434(2) yes O4 H1O4 . . .94(2) no C1 C2 . . 1.403(2) no C1 C6 . . 1.392(2) no C1 C7 . . 1.492(2) no C2 C3 . . 1.384(2) no C3 C4 . . 1.391(2) no C3 H3 . . .98 no C4 C5 . . 1.383(2) no C4 H4 . . .98 no C5 C6 . . 1.396(2) no C5 C14 . . 1.502(2) yes C6 H6 . . .98 no C7 C8 . . 1.407(2) no C7 C12 . . 1.388(2) no C8 C9 . . 1.387(2) no C9 C10 . . 1.388(2) no C9 H9 . . .98 no C10 C11 . . 1.383(2) no C10 H10 . . .98 no C11 C12 . . 1.398(2) no C11 C16 . . 1.506(2) yes C12 H12 . . .98 no C13 H13C . . .98 no C13 H13A . . .98 no C13 H13B . . .98 no C14 H14A . . .98 no C14 H14B . . .98 no C15 H15B . . .98 no C15 H15C . . .98 no C15 H15A . . .98 no C16 H16A . . .98 no C16 H16B . . .98 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag O2 H1O2 O4 2_546 .89(2) 1.92(2) 2.7610(10) 157(2) yes O4 H1O4 O2 4_544 .94(2) 1.77(2) 2.6990(10) 168(2) yes C10 H10 O1 2_646 .98 2.41 3.2010(10) 137 yes C3 H3 O4 4_555 .98 2.52 3.4900(10) 170 yes C12 H12 O2 2_556 .98 2.67 3.380(2) 129 yes C15 H15C O1 3_657 .98 2.69 3.574(2) 150 yes C4 H4 O2 3_557 .98 2.72 3.377(2) 125 yes C14 H14A O1 2_546 .98 2.76 3.637(2) 149 yes C13 H13C O4 4_555 .98 2.76 3.557(2) 139 yes 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_publ_flag O1 C2 C1 C6 -175.00(10) no O1 C2 C1 C7 1.6(2) no O1 C2 C3 C4 176.90(10) no O2 C14 C5 C4 -96.10(10) no O2 C14 C5 C6 80.30(10) no O3 C8 C7 C1 -.1(2) no O3 C8 C7 C12 -179.40(10) no O3 C8 C9 C10 -179.40(10) no O4 C16 C11 C10 -137.30(10) no O4 C16 C11 C12 42.4(2) no C1 C2 O1 C13 160.20(10) yes C1 C2 C3 C4 -1.5(2) no C1 C6 C5 C4 -.8(2) no C1 C6 C5 C14 -177.20(10) no C1 C7 C8 C9 178.70(10) no C1 C7 C12 C11 179.20(10) no C2 C1 C6 C5 -2.3(2) no C2 C1 C7 C8 69.0(2) yes C2 C1 C7 C12 -111.60(10) yes C2 C3 C4 C5 -1.7(2) no C3 C2 O1 C13 -18.3(2) no C3 C2 C1 C6 3.4(2) no C3 C2 C1 C7 -180.00(10) no C3 C4 C5 C6 2.8(2) no C3 C4 C5 C14 179.30(10) no C5 C6 C1 C7 -178.90(10) no C6 C1 C7 C8 -114.50(10) no C6 C1 C7 C12 64.90(10) no C7 C8 O3 C15 179.10(10) yes C7 C8 C9 C10 1.9(2) no C7 C12 C11 C10 2.1(2) no C7 C12 C11 C16 -177.60(10) no C8 C7 C12 C11 -1.4(2) no C8 C9 C10 C11 -1.1(2) no C9 C8 O3 C15 .3(2) no C9 C8 C7 C12 -.7(2) no C9 C10 C11 C12 -.8(2) no C9 C10 C11 C16 178.90(10) no loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 558084 2 PubChem 642903