#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:43:10 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301803 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/45/2204577.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_2204577 loop_ _publ_author_name 'Iain D. H. Oswald' 'W. D. Sam Motherwell' 'Simon Parsons' _publ_section_title ; A 1:1 co-crystal of quinol and pyridine ; _journal_issue 11 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o1967 _journal_page_last o1969 _journal_paper_doi 10.1107/S1600536804024547 _journal_volume 60 _journal_year 2004 _chemical_formula_iupac 'C6 H6 O2, C5 H5 N' _chemical_formula_moiety 'C6 H6 O2, C5 H5 N' _chemical_formula_sum 'C11 H11 N O2' _chemical_formula_weight 189.21 _chemical_name_common Quinol--Pyridine _chemical_name_systematic ; Quinol--Pyridine (1/1) ; _space_group_IT_number 2 _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_hydrogens 'geom and difmap (OH)' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 89.002(2) _cell_angle_beta 76.222(2) _cell_angle_gamma 77.478(2) _cell_formula_units_Z 2 _cell_length_a 5.7451(5) _cell_length_b 9.1570(9) _cell_length_c 9.6247(9) _cell_measurement_reflns_used 2033 _cell_measurement_temperature 150(2) _cell_measurement_theta_max 29 _cell_measurement_theta_min 2 _cell_volume 479.76(8) _computing_cell_refinement 'SAINT (Bruker--Nonius, 2003)' _computing_data_collection 'SMART (Bruker--Nonius, 2001)' _computing_data_reduction SAINT _computing_molecular_graphics SHELXTL _computing_publication_material ; SHELXTL, PLATON [Spek (2004) as incorporated in WinGX (Farrugia, 1999)] and enCIFer (Version 1.1; Allen et al., 2004) ; _computing_structure_refinement SHELXTL _computing_structure_solution 'SHELXTL (Sheldrick, 2001)' _diffrn_ambient_temperature 150(2) _diffrn_measured_fraction_theta_full 0.995 _diffrn_measured_fraction_theta_max 0.905 _diffrn_measurement_device_type 'Bruker APEX CCD area-detector' _diffrn_measurement_method \w _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.018 _diffrn_reflns_av_sigmaI/netI 0.0343 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 4349 _diffrn_reflns_theta_full 25.24 _diffrn_reflns_theta_max 28.73 _diffrn_reflns_theta_min 2.18 _diffrn_standards_decay_% 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.091 _exptl_absorpt_correction_T_max 0.980 _exptl_absorpt_correction_T_min 0.841 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 2004)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.310 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 200 _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.18 _refine_diff_density_max 0.28 _refine_diff_density_min -0.21 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 135 _refine_ls_number_reflns 2248 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.039 _refine_ls_R_factor_all 0.058 _refine_ls_R_factor_gt 0.048 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.049P)^2^+0.1585P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.113 _refine_ls_wR_factor_ref 0.120 _reflns_number_gt 1853 _reflns_number_total 2248 _reflns_threshold_expression I>2\S(I) _cod_data_source_file wk6031.cif _cod_data_source_block I _cod_original_sg_symbol_Hall -P1 _cod_database_code 2204577 _cod_database_fobs_code 2204577 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -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_refinement_flags _atom_site_occupancy _atom_site_type_symbol O1A 1.3232(2) 0.07757(13) 0.26274(12) 0.0362(3) Uani d . 1 O H1A 1.344(4) 0.174(3) 0.281(2) 0.065(7) Uiso d . 1 H C1A 1.1638(3) 0.04088(16) 0.38221(16) 0.0263(3) Uani d . 1 C C2A 1.1609(3) 0.08591(16) 0.51998(17) 0.0278(3) Uani d . 1 C H2A 1.2717 0.1445 0.5340 0.033 Uiso calc R 1 H C3A 0.9969(3) 0.04557(16) 0.63687(16) 0.0283(3) Uani d . 1 C H3A 0.9948 0.0775 0.7306 0.034 Uiso calc R 1 H O1B 0.3575(2) 0.36954(12) 0.28535(12) 0.0290(3) Uani d . 1 O H1B 0.268(4) 0.441(3) 0.238(2) 0.057(6) Uiso d . 1 H C1B 0.4247(3) 0.43589(16) 0.39227(15) 0.0239(3) Uani d . 1 C C2B 0.6167(3) 0.35608(16) 0.44644(16) 0.0256(3) Uani d . 1 C H2B 0.6960 0.2573 0.4106 0.031 Uiso calc R 1 H C3B 0.6928(3) 0.42029(16) 0.55269(16) 0.0252(3) Uani d . 1 C H3B 0.8258 0.3657 0.5881 0.030 Uiso calc R 1 H N1S 0.8953(2) 0.41739(14) -0.14401(14) 0.0283(3) Uani d . 1 N C2S 0.8062(3) 0.34857(18) -0.02635(17) 0.0330(4) Uani d . 1 C H2S 0.6370 0.3800 0.0198 0.040 Uiso calc R 1 H C3S 0.9484(4) 0.2340(2) 0.03146(18) 0.0408(4) Uani d . 1 C H3S 0.8787 0.1883 0.1160 0.049 Uiso calc R 1 H C4S 1.1934(4) 0.1870(2) -0.03559(19) 0.0398(4) Uani d . 1 C H4S 1.2952 0.1076 0.0013 0.048 Uiso calc R 1 H C5S 1.2883(3) 0.25698(19) -0.15699(18) 0.0348(4) Uani d . 1 C H5S 1.4567 0.2272 -0.2052 0.042 Uiso calc R 1 H C6S 1.1336(3) 0.37130(18) -0.20724(17) 0.0300(3) Uani d . 1 C H6S 1.1997 0.4196 -0.2909 0.036 Uiso calc R 1 H 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 O1A 0.0467(7) 0.0270(6) 0.0325(6) -0.0101(5) -0.0030(5) 0.0004(5) C1A 0.0313(8) 0.0171(6) 0.0285(8) -0.0004(6) -0.0075(6) 0.0016(5) C2A 0.0311(8) 0.0199(7) 0.0341(8) -0.0040(6) -0.0123(6) -0.0008(6) C3A 0.0379(8) 0.0202(7) 0.0267(7) -0.0015(6) -0.0118(6) -0.0013(5) O1B 0.0364(6) 0.0207(5) 0.0317(6) -0.0040(4) -0.0136(5) 0.0021(4) C1B 0.0261(7) 0.0197(7) 0.0258(7) -0.0054(5) -0.0057(6) 0.0038(5) C2B 0.0269(7) 0.0167(7) 0.0303(8) -0.0008(5) -0.0051(6) 0.0021(5) C3B 0.0244(7) 0.0200(7) 0.0296(8) -0.0011(5) -0.0070(6) 0.0045(5) N1S 0.0329(7) 0.0242(6) 0.0292(7) -0.0052(5) -0.0110(5) 0.0024(5) C2S 0.0351(8) 0.0323(8) 0.0288(8) -0.0043(7) -0.0048(7) 0.0001(6) C3S 0.0556(11) 0.0361(9) 0.0266(8) -0.0049(8) -0.0072(8) 0.0075(7) C4S 0.0510(11) 0.0316(9) 0.0353(9) 0.0048(8) -0.0199(8) 0.0011(7) C5S 0.0313(8) 0.0348(9) 0.0377(9) -0.0026(7) -0.0111(7) -0.0049(7) C6S 0.0329(8) 0.0286(8) 0.0317(8) -0.0111(6) -0.0098(6) 0.0030(6) 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' N N 0.0061 0.0033 '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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle C1A O1A H1A . . 107.2(14) O1A C1A C3A . 2_756 118.11(14) O1A C1A C2A . . 122.49(14) C3A C1A C2A 2_756 . 119.40(14) C3A C2A C1A . . 120.20(14) C3A C2A H2A . . 119.9 C1A C2A H2A . . 119.9 C1A C3A C2A 2_756 . 120.40(14) C1A C3A H3A 2_756 . 119.8 C2A C3A H3A . . 119.8 C1B O1B H1B . . 110.5(14) O1B C1B C2B . . 118.52(13) O1B C1B C3B . 2_666 122.17(13) C2B C1B C3B . 2_666 119.31(14) C3B C2B C1B . . 120.23(13) C3B C2B H2B . . 119.9 C1B C2B H2B . . 119.9 C2B C3B C1B . 2_666 120.45(13) C2B C3B H3B . . 119.8 C1B C3B H3B 2_666 . 119.8 C2S N1S C6S . . 117.48(14) N1S C2S C3S . . 123.05(16) N1S C2S H2S . . 118.5 C3S C2S H2S . . 118.5 C4S C3S C2S . . 118.77(16) C4S C3S H3S . . 120.6 C2S C3S H3S . . 120.6 C5S C4S C3S . . 118.90(16) C5S C4S H4S . . 120.6 C3S C4S H4S . . 120.6 C4S C5S C6S . . 118.62(16) C4S C5S H5S . . 120.7 C6S C5S H5S . . 120.7 N1S C6S C5S . . 123.18(15) N1S C6S H6S . . 118.4 C5S C6S H6S . . 118.4 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance O1A C1A . 1.3755(19) O1A H1A . 0.94(3) C1A C3A 2_756 1.384(2) C1A C2A . 1.391(2) C2A C3A . 1.386(2) C2A H2A . 0.9500 C3A C1A 2_756 1.384(2) C3A H3A . 0.9500 O1B C1B . 1.3745(18) O1B H1B . 0.93(2) C1B C2B . 1.391(2) C1B C3B 2_666 1.392(2) C2B C3B . 1.389(2) C2B H2B . 0.9500 C3B C1B 2_666 1.392(2) C3B H3B . 0.9500 N1S C2S . 1.334(2) N1S C6S . 1.336(2) C2S C3S . 1.379(2) C2S H2S . 0.9500 C3S C4S . 1.377(3) C3S H3S . 0.9500 C4S C5S . 1.377(3) C4S H4S . 0.9500 C5S C6S . 1.380(2) C5S H5S . 0.9500 C6S H6S . 0.9500 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 O1A H1A O1B 1_655 0.94(3) 1.81(3) 2.7392(16) 168(2) yes O1B H1B N1S 2_665 0.93(2) 1.79(2) 2.7178(17) 178(2) yes C2S H2S O1B . 0.95 2.69 3.436(2) 136 yes C4S H4S O1A . 0.95 2.57 3.225(2) 127 yes C6S H6S X1B 1_654 0.95 2.53 3.45 162 yes loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 139067164