#------------------------------------------------------------------------------ #$Date: 2026-01-20 17:05:02 +0000 (Tue, 20 Jan 2026) $ #$Revision: 304193 $ #$URL: svn://www.crystallography.net/cod/cif/3/50/01/3500149.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_3500149 loop_ _publ_author_name 'Thierry Maris' _publ_section_references ; Bourhis, L.J., Dolomanov, O.V., Gildea, R.J., Howard, J.A.K., Puschmann, H. (2015). Acta Cryst. A71, 59-75. Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H. (2009), J. Appl. Cryst. 42, 339-341. Kleemiss, F., Dolomanov, O.V., Bodensteiner, M., Peyerimhoff, N., Midgley, L., Bourhis, L.J., Genoni, A., Malaspina, L.A., Jayatilaka, D., Spencer, J.L., White, F., Grundkoetter-Stock, B., Steinhauer, S., Lentz, D., Puschmann, H., Grabowsky, S. (2021), Chem. Sci., 12, 1675-1692. Sheldrick, G.M. (2015). Acta Cryst. A71, 3-8. ; _publ_section_title ; Non spherical atom form-factors refinement of 4-Hydroxybiphenyl ; _journal_name_full 'Personal communication to COD' _journal_year 2026 _chemical_formula_moiety 'C12 H10 O' _chemical_formula_sum 'C12 H10 O' _chemical_formula_weight 170.213 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 1' _symmetry_Int_Tables_number 14 _atom_sites_solution_primary dual _audit_creation_date 2026-01-20 _audit_creation_method ; Olex2 1.5 (compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7314) ; _cell_angle_alpha 90 _cell_angle_beta 94.460(1) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 19.9626(5) _cell_length_b 5.4251(1) _cell_length_c 7.9004(2) _cell_measurement_reflns_used 9198 _cell_measurement_temperature 150 _cell_measurement_theta_max 63.492 _cell_measurement_theta_min 5.804 _cell_volume 853.02(3) _computing_cell_refinement ; SAINT (2013) V8.42; Integration Software for Single Crystal Data. Bruker AXS Inc., Madison, WI 53719-1173. ; _computing_data_collection ; APEX 4 (2022) Bruker AXS Inc., Madison, WI 53719-1173. ; _computing_data_reduction ; SAINT (2013) V8.42; Integration Software for Single Crystal Data. Bruker AXS Inc., Madison, WI 53719-1173. ; _computing_molecular_graphics 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_structure_refinement 'olex2.refine 1.5 (Bourhis et al., 2015)' _computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2018)' _diffrn_ambient_temperature 150 _diffrn_detector 'CMOS Area detector' _diffrn_detector_area_resol_mean 10.42 _diffrn_detector_type 'Bruker CMOS Photon III ' _diffrn_measured_fraction_theta_full 0.9909 _diffrn_measured_fraction_theta_max 0.9930 _diffrn_measurement_device 'k-geometry diffractometer' _diffrn_measurement_device_type 'Bruker Venture Metaljet' _diffrn_measurement_method '\w and \f scans' _diffrn_radiation_collimation 'Focusing mirrors' _diffrn_radiation_monochromator 'Helios MX Mirror Optics' _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Ga K\a' _diffrn_radiation_wavelength 1.34139 _diffrn_reflns_av_R_equivalents 0.0494 _diffrn_reflns_av_unetI/netI 0.0272 _diffrn_reflns_Laue_measured_fraction_full 0.9909 _diffrn_reflns_Laue_measured_fraction_max 0.9930 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_number 25735 _diffrn_reflns_point_group_measured_fraction_full 0.9909 _diffrn_reflns_point_group_measured_fraction_max 0.9930 _diffrn_reflns_theta_full 53.5942 _diffrn_reflns_theta_max 63.46 _diffrn_reflns_theta_min 1.93 _diffrn_source 'Metal Jet' _diffrn_source_current 3.57 _diffrn_source_power 0.249 _diffrn_source_target Ga _diffrn_source_type 'Gallium Liquid Metal Jet Source' _diffrn_source_voltage 69.71 _exptl_absorpt_coefficient_mu 0.432 _exptl_absorpt_correction_T_max 0.2667 _exptl_absorpt_correction_T_min 0.1440 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1875 before and 0.1016 after correction. The Ratio of minimum to maximum transmission is 0.5399. The \l/2 correction factor is Not present. ; _exptl_crystal_colour 'clear light colourless' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.325 _exptl_crystal_description plate _exptl_crystal_F_000 360.814 _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.03 _exptl_special_details ; X-ray crystallographic data for I were collected from a single crystal sample, which was mounted on a loop fiber. Data were collected using a Bruker Venture diffractometer equipped with a Photon III CMOS Detector, a Helios MX optics and a Kappa goniometer. The crystal-to-detector distance was 4.0 cm, and the data collection was carried out in 1024 x 1024 pixel mode. ; _refine_diff_density_max 0.3452 _refine_diff_density_min -0.3218 _refine_diff_density_rms 0.0570 _refine_ls_d_res_high 0.7497 _refine_ls_d_res_low 19.9022 _refine_ls_goodness_of_fit_ref 1.1135 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_constraints 0 _refine_ls_number_parameters 208 _refine_ls_number_reflns 2113 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.1135 _refine_ls_R_factor_all 0.0441 _refine_ls_R_factor_gt 0.0422 _refine_ls_shift/su_max 0.0002 _refine_ls_shift/su_mean 0.0000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.1033P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1253 _refine_ls_wR_factor_ref 0.1291 _refine_special_details ; Refinement using NoSpherA2, an implementation of NOn-SPHERical Atom-form-factors in Olex2. Please cite: F. Kleemiss et al. Chem. Sci. DOI 10.1039/D0SC05526C - 2021 NoSpherA2 implementation of HAR makes use of tailor-made aspherical atomic form factors calculated on-the-fly from a Hirshfeld-partitioned electron density (ED) - not from spherical-atom form factors. The ED is calculated from a gaussian basis set single determinant SCF wavefunction - either Hartree-Fock or DFT using selected funtionals - for a fragment of the crystal. This fragment can be embedded in an electrostatic crystal field by employing cluster charges or modelled using implicit solvation models, depending on the software used. The following options were used: SOFTWARE: ORCA 6.0 PARTITIONING: NoSpherA2 INT ACCURACY: Max METHOD: r2SCAN BASIS SET: cc-pVTZ CHARGE: 0 MULTIPLICITY: 1 DATE: 2026-01-20_09-01-42 ; _reflns_Friedel_coverage 0.0 _reflns_limit_h_max 26 _reflns_limit_h_min -26 _reflns_limit_k_max 7 _reflns_limit_k_min 0 _reflns_limit_l_max 10 _reflns_limit_l_min 0 _reflns_number_gt 1917 _reflns_number_total 2113 _reflns_threshold_expression I>=2u(I) _cod_data_source_file diphenoh_cod.cif _cod_data_source_block diphenoh _cod_database_code 3500149 loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 x,y,z 2 -x,y+1/2,-z+1/2 3 -x,-y,-z 4 x,-y-1/2,z-1/2 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_refinement_flags_posn O1 O 0.52671(2) 0.50894(9) 0.25359(6) 0.03090(19) Uani 1.000000 . C1 C 0.59169(3) 0.50190(9) 0.32475(7) 0.02301(19) Uani 1.000000 . C2 C 0.61514(3) 0.31291(11) 0.43262(7) 0.02564(19) Uani 1.000000 . C3 C 0.68182(3) 0.31365(10) 0.49951(7) 0.02469(19) Uani 1.000000 . C4 C 0.72637(3) 0.50230(8) 0.46272(7) 0.01937(19) Uani 1.000000 . C5 C 0.70089(3) 0.69119(10) 0.35523(7) 0.02422(19) Uani 1.000000 . C6 C 0.63466(3) 0.69195(11) 0.28616(8) 0.02617(19) Uani 1.000000 . C7 C 0.79779(3) 0.50054(8) 0.53355(7) 0.01966(19) Uani 1.000000 . C8 C 0.82271(3) 0.31363(11) 0.64328(8) 0.02650(19) Uani 1.000000 . C9 C 0.88972(3) 0.30978(12) 0.70808(8) 0.0297(2) Uani 1.000000 . C10 C 0.93384(3) 0.49290(10) 0.66422(7) 0.0275(2) Uani 1.000000 . C11 C 0.90998(3) 0.68084(12) 0.55619(8) 0.0294(2) Uani 1.000000 . C12 C 0.84297(3) 0.68507(11) 0.49217(8) 0.02716(19) Uani 1.000000 . H10 H 0.9863(4) 0.4874(13) 0.7134(13) 0.043(2) Uani 1.000000 . H5 H 0.7324(4) 0.8382(16) 0.3246(13) 0.047(2) Uani 1.000000 . H3 H 0.6980(4) 0.1609(15) 0.5836(12) 0.047(3) Uani 1.000000 . H6 H 0.6174(4) 0.8390(16) 0.1989(14) 0.048(3) Uani 1.000000 . H11 H 0.9435(5) 0.8259(16) 0.5198(13) 0.052(3) Uani 1.000000 . H8 H 0.7899(4) 0.1696(16) 0.6772(14) 0.057(3) Uani 1.000000 . H9 H 0.9069(4) 0.1579(16) 0.7949(14) 0.058(3) Uani 1.000000 . H12 H 0.8268(5) 0.8370(16) 0.4084(13) 0.052(3) Uani 1.000000 . H2 H 0.5810(5) 0.1681(16) 0.4648(13) 0.052(3) Uani 1.000000 . H1 H 0.5064(5) 0.348(3) 0.2606(14) 0.053(3) Uani 1.000000 . 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 0.0213(3) 0.0306(3) 0.0399(3) 0.00053(16) -0.0039(2) 0.00171(17) C1 0.0207(3) 0.0224(3) 0.0258(3) 0.00050(17) 0.0006(2) 0.00007(17) C2 0.0226(3) 0.0241(3) 0.0296(3) -0.0040(2) -0.0015(2) 0.00358(19) C3 0.0239(3) 0.0217(3) 0.0277(3) -0.0036(2) -0.0024(2) 0.00553(19) C4 0.0203(3) 0.0187(3) 0.0192(3) 0.00026(16) 0.0021(2) 0.00046(15) C5 0.0210(3) 0.0222(3) 0.0294(3) -0.0006(2) 0.0018(2) 0.00705(19) C6 0.0223(3) 0.0242(3) 0.0316(3) 0.0009(2) -0.0003(2) 0.0065(2) C7 0.0203(3) 0.0192(3) 0.0196(3) 0.00018(17) 0.0022(2) 0.00014(16) C8 0.0213(3) 0.0267(3) 0.0314(3) 0.0011(2) 0.0016(2) 0.0091(2) C9 0.0220(3) 0.0320(4) 0.0350(3) 0.0030(2) -0.0001(2) 0.0082(2) C10 0.0216(4) 0.0323(4) 0.0282(3) 0.00029(19) -0.0003(2) 0.00036(19) C11 0.0235(4) 0.0304(4) 0.0337(3) -0.0061(2) -0.0020(2) 0.0038(2) C12 0.0246(3) 0.0248(3) 0.0312(3) -0.0048(2) -0.0032(2) 0.0060(2) H10 0.019(5) 0.043(5) 0.064(6) -0.002(3) -0.014(4) 0.005(4) H5 0.035(5) 0.044(5) 0.061(6) -0.001(4) -0.004(5) 0.020(5) H3 0.031(5) 0.046(6) 0.062(6) 0.001(4) -0.013(4) 0.029(5) H6 0.032(5) 0.044(5) 0.067(7) -0.002(4) -0.009(5) 0.024(5) H11 0.041(5) 0.046(6) 0.066(6) -0.017(4) -0.010(5) 0.023(5) H8 0.041(5) 0.049(6) 0.079(7) -0.013(4) -0.007(5) 0.030(5) H9 0.039(6) 0.046(6) 0.087(8) 0.009(4) -0.005(6) 0.044(6) H12 0.039(5) 0.043(6) 0.073(7) -0.010(4) -0.010(5) 0.030(5) H2 0.044(6) 0.047(6) 0.061(6) -0.026(4) -0.011(5) 0.020(5) H1 0.029(5) 0.070(7) 0.060(7) -0.013(5) 0.000(5) -0.008(5) loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source _atom_type_scat_dispersion_source C 0.01370 0.00670 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C' 'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850' H -0.00000 0.00000 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C' 'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850' O 0.03890 0.02410 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C' 'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850' 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 H1 O1 C1 109.7(6) . . C2 C1 O1 122.24(5) . . C6 C1 O1 117.96(5) . . C6 C1 C2 119.81(6) . . C3 C2 C1 119.75(5) . . H2 C2 C1 119.4(5) . . H2 C2 C3 120.9(5) . . C4 C3 C2 121.77(5) . . H3 C3 C2 117.1(4) . . H3 C3 C4 121.1(4) . . C5 C4 C3 116.98(6) . . C7 C4 C3 121.43(5) . . C7 C4 C5 121.59(5) . . C6 C5 C4 121.96(5) . . H5 C5 C4 119.8(4) . . H5 C5 C6 118.3(5) . . C5 C6 C1 119.72(5) . . H6 C6 C1 120.6(5) . . H6 C6 C5 119.6(5) . . C8 C7 C4 121.37(5) . . C12 C7 C4 121.43(5) . . C12 C7 C8 117.20(6) . . C9 C8 C7 121.50(5) . . H8 C8 C7 119.4(5) . . H8 C8 C9 119.1(5) . . C10 C9 C8 120.41(5) . . H9 C9 C8 118.6(5) . . H9 C9 C10 121.0(5) . . C11 C10 C9 118.96(6) . . H10 C10 C9 120.1(4) . . H10 C10 C11 120.9(4) . . C12 C11 C10 120.57(5) . . H11 C11 C10 120.3(5) . . H11 C11 C12 119.1(5) . . C11 C12 C7 121.35(5) . . H12 C12 C7 121.0(5) . . H12 C12 C11 117.7(5) . . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 O1 C1 1.3735(7) . O1 H1 0.968(14) . C1 C2 1.3909(8) . C1 C6 1.3901(8) . C2 C3 1.3935(8) . C2 H2 1.083(8) . C3 C4 1.4011(8) . C3 H3 1.095(7) . C4 C5 1.4010(7) . C4 C7 1.4906(9) . C5 C6 1.3905(8) . C5 H5 1.056(9) . C6 H6 1.093(8) . C7 C8 1.4000(7) . C7 C12 1.4031(8) . C8 C9 1.3949(8) . C8 H8 1.067(8) . C9 C10 1.3893(9) . C9 H9 1.109(8) . C10 C11 1.3898(8) . C10 H10 1.090(8) . C11 C12 1.3930(8) . C11 H11 1.086(8) . C12 H12 1.090(8) . 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 O1 C1 C2 C3 179.21(6) . . . . O1 C1 C6 C5 -179.81(6) . . . . C1 C2 C3 C4 0.73(6) . . . . C1 C6 C5 C4 0.51(7) . . . . C2 C1 C6 C5 0.25(6) . . . . C2 C3 C4 C5 0.00(6) . . . . C2 C3 C4 C7 -179.44(6) . . . . C3 C2 C1 C6 -0.85(6) . . . . C3 C4 C5 C6 -0.62(6) . . . . C3 C4 C7 C8 -1.71(6) . . . . C3 C4 C7 C12 177.84(7) . . . . C4 C7 C8 C9 179.18(6) . . . . C4 C7 C12 C11 -178.89(6) . . . . C5 C4 C7 C8 178.87(7) . . . . C5 C4 C7 C12 -1.58(6) . . . . C6 C5 C4 C7 178.82(6) . . . . C7 C8 C9 C10 -0.25(7) . . . . C7 C12 C11 C10 -0.34(7) . . . . C8 C7 C12 C11 0.68(6) . . . . C8 C9 C10 C11 0.60(7) . . . . C9 C8 C7 C12 -0.39(6) . . . . C9 C10 C11 C12 -0.31(6) . . . . _cod_database_fobs_code 3500149