#------------------------------------------------------------------------------ #$Date: 2013-08-29 18:37:19 +0300 (Thu, 29 Aug 2013) $ #$Revision: 88064 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/20/86/2208696.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_2208696 loop_ _publ_author_name 'Zhi-Xiong Liu' 'Meng, Xiang-Gao' _publ_section_title ; A 1:1 cocrystal of 8-hydroxyquinoline and 5-methyl-1H-imidazole ; _journal_coeditor_code RZ2005 _journal_issue 4 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o1286 _journal_page_last o1288 _journal_volume 62 _journal_year 2006 _chemical_formula_iupac 'C9 H7 N O, C4 H6 N2' _chemical_formula_moiety 'C9 H7 N O, C4 H6 N2' _chemical_formula_sum 'C13 H13 N3 O' _chemical_formula_weight 227.26 _chemical_name_systematic ; 8-hydroxyquinoline--5-methyl-1H-imidazole (1/1) ; _space_group_IT_number 19 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_space_group_name_H-M 'P 21 21 21' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 7.259(3) _cell_length_b 9.109(3) _cell_length_c 18.334(7) _cell_measurement_reflns_used 878 _cell_measurement_temperature 292(2) _cell_measurement_theta_max 15.94 _cell_measurement_theta_min 3.01 _cell_volume 1212.3(8) _computing_cell_refinement 'SAINT-Plus (Bruker, 2001)' _computing_data_collection 'SMART (Bruker, 2001)' _computing_data_reduction SAINT-Plus _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material PLATON _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 292(2) _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.997 _diffrn_measurement_device_type 'Bruker SMART APEX CCD area-detector' _diffrn_measurement_method '0.3\% wide \w exposures' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine focus sealed Siemens Mo tube' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0997 _diffrn_reflns_av_sigmaI/netI 0.0656 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_number 10211 _diffrn_reflns_theta_full 27.00 _diffrn_reflns_theta_max 27.00 _diffrn_reflns_theta_min 2.22 _diffrn_standards_decay_% 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_T_max 0.9984 _exptl_absorpt_correction_T_min 0.9838 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 2003)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.245 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 480 _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.02 _refine_diff_density_max 0.121 _refine_diff_density_min -0.160 _refine_ls_extinction_coef 0.011(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL97 _refine_ls_goodness_of_fit_ref 1.000 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 156 _refine_ls_number_reflns 1537 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.000 _refine_ls_R_factor_all 0.1152 _refine_ls_R_factor_gt 0.0593 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0561P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1143 _refine_ls_wR_factor_ref 0.1288 _reflns_number_gt 900 _reflns_number_total 1537 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file rz2005.cif _[local]_cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius The following automatic conversions were performed: '_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_database_code 2208696 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' loop_ _atom_site_type_symbol _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 C C1 0.2349(5) 0.5184(4) 1.02759(19) 0.0472(10) Uani d . 1 C C2 0.3940(5) 0.4752(4) 1.06545(19) 0.0511(10) Uani d . 1 C C3 0.5260(6) 0.3963(5) 1.0297(2) 0.0650(12) Uani d . 1 H H3 0.6303 0.3650 1.0548 0.078 Uiso calc R 1 C C4 0.5056(6) 0.3619(5) 0.9556(3) 0.0736(13) Uani d . 1 H H4 0.5977 0.3092 0.9319 0.088 Uiso calc R 1 C C5 0.3548(6) 0.4040(5) 0.9179(2) 0.0683(13) Uani d . 1 H H5 0.3441 0.3815 0.8686 0.082 Uiso calc R 1 C C6 0.2150(6) 0.4815(4) 0.9532(2) 0.0532(10) Uani d . 1 C C7 0.0503(6) 0.5256(5) 0.9188(2) 0.0665(12) Uani d . 1 H H7 0.0296 0.5014 0.8702 0.080 Uiso calc R 1 C C8 -0.0777(6) 0.6030(6) 0.9562(2) 0.0741(12) Uani d . 1 H H8 -0.1862 0.6332 0.9338 0.089 Uiso calc R 1 C C9 -0.0433(6) 0.6360(5) 1.0287(2) 0.0687(12) Uani d . 1 H H9 -0.1326 0.6892 1.0537 0.082 Uiso calc R 1 C C10 0.4529(5) 0.1854(4) 0.7478(2) 0.0495(9) Uani d . 1 C C11 0.3617(5) 0.1030(4) 0.7966(2) 0.0574(11) Uani d . 1 H H11 0.4178 0.0415 0.8305 0.069 Uiso calc R 1 C C12 0.1556(5) 0.2170(5) 0.73763(19) 0.0593(11) Uani d . 1 H H12 0.0427 0.2524 0.7213 0.071 Uiso calc R 1 C C13 0.6539(5) 0.2049(5) 0.7329(2) 0.0788(14) Uani d . 1 H H13A 0.6778 0.1873 0.6821 0.118 Uiso calc R 1 H H13B 0.7232 0.1366 0.7618 0.118 Uiso calc R 1 H H13C 0.6898 0.3032 0.7451 0.118 Uiso calc R 1 N N1 0.1051(4) 0.5981(4) 1.06480(15) 0.0548(9) Uani d . 1 N N2 0.3189(4) 0.2578(3) 0.71020(15) 0.0503(8) Uani d . 1 H H2 0.3360 0.3189 0.6751 0.060 Uiso calc R 1 N N3 0.1750(4) 0.1213(4) 0.79010(17) 0.0631(9) Uani d . 1 O O1 0.4083(3) 0.5123(3) 1.13640(13) 0.0678(9) Uani d . 1 H H1 0.5052 0.4802 1.1529 0.102 Uiso calc R 1 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 C1 0.049(2) 0.038(2) 0.054(2) 0.0006(18) 0.0014(18) 0.0050(19) C2 0.056(2) 0.051(3) 0.046(2) 0.008(2) -0.0021(19) 0.0003(19) C3 0.062(3) 0.065(3) 0.069(3) 0.017(2) -0.001(2) 0.003(2) C4 0.077(3) 0.074(3) 0.070(3) 0.018(3) 0.008(2) -0.013(3) C5 0.087(3) 0.062(3) 0.056(2) 0.000(3) -0.002(2) -0.012(2) C6 0.065(3) 0.042(2) 0.053(2) -0.005(2) -0.002(2) 0.004(2) C7 0.085(3) 0.062(3) 0.053(2) -0.002(3) -0.011(2) 0.001(2) C8 0.068(3) 0.087(3) 0.068(3) 0.009(3) -0.009(2) 0.013(3) C9 0.064(3) 0.082(3) 0.061(3) 0.021(2) 0.000(2) 0.013(3) C10 0.049(2) 0.053(2) 0.047(2) 0.0013(19) 0.0013(19) -0.002(2) C11 0.066(3) 0.055(3) 0.052(2) -0.002(2) -0.0017(19) 0.006(2) C12 0.042(2) 0.083(3) 0.053(2) -0.009(2) -0.0025(18) 0.005(2) C13 0.050(2) 0.088(3) 0.099(4) 0.012(2) 0.006(2) 0.018(3) N1 0.0529(19) 0.064(2) 0.0478(18) 0.0078(19) -0.0013(15) 0.0094(17) N2 0.0451(17) 0.061(2) 0.0445(16) -0.0105(18) 0.0053(14) 0.0081(16) N3 0.058(2) 0.077(3) 0.0541(19) -0.010(2) 0.0055(16) 0.008(2) O1 0.0641(17) 0.092(2) 0.0476(15) 0.0279(16) -0.0107(13) -0.0057(15) 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' N N 0.0061 0.0000 '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 N1 C1 C2 117.9(3) N1 C1 C6 122.4(3) C2 C1 C6 119.7(3) O1 C2 C3 122.7(4) O1 C2 C1 118.1(3) C3 C2 C1 119.2(3) C2 C3 C4 120.5(4) C2 C3 H3 119.7 C4 C3 H3 119.7 C5 C4 C3 121.2(4) C5 C4 H4 119.4 C3 C4 H4 119.4 C4 C5 C6 119.7(4) C4 C5 H5 120.1 C6 C5 H5 120.1 C5 C6 C7 123.6(4) C5 C6 C1 119.6(4) C7 C6 C1 116.8(4) C8 C7 C6 120.3(4) C8 C7 H7 119.8 C6 C7 H7 119.8 C7 C8 C9 118.4(4) C7 C8 H8 120.8 C9 C8 H8 120.8 N1 C9 C8 125.1(4) N1 C9 H9 117.4 C8 C9 H9 117.4 C11 C10 N2 104.8(3) C11 C10 C13 132.0(3) N2 C10 C13 123.2(3) C10 C11 N3 111.2(3) C10 C11 H11 124.4 N3 C11 H11 124.4 N3 C12 N2 111.5(3) N3 C12 H12 124.2 N2 C12 H12 124.2 C10 C13 H13A 109.5 C10 C13 H13B 109.5 H13A C13 H13B 109.5 C10 C13 H13C 109.5 H13A C13 H13C 109.5 H13B C13 H13C 109.5 C9 N1 C1 116.9(3) C12 N2 C10 107.9(3) C12 N2 H2 126.0 C10 N2 H2 126.0 C12 N3 C11 104.6(3) C2 O1 H1 109.5 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance C1 N1 1.371(4) C1 C2 1.404(5) C1 C6 1.412(5) C2 O1 1.348(4) C2 C3 1.366(5) C3 C4 1.403(6) C3 H3 0.9300 C4 C5 1.350(6) C4 H4 0.9300 C5 C6 1.396(5) C5 H5 0.9300 C6 C7 1.410(5) C7 C8 1.352(6) C7 H7 0.9300 C8 C9 1.385(6) C8 H8 0.9300 C9 N1 1.311(5) C9 H9 0.9300 C10 C11 1.343(5) C10 N2 1.363(4) C10 C13 1.495(5) C11 N3 1.371(5) C11 H11 0.9300 C12 N3 1.305(4) C12 N2 1.340(4) C12 H12 0.9300 C13 H13A 0.9600 C13 H13B 0.9600 C13 H13C 0.9600 N2 H2 0.8600 O1 H1 0.8200 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 C5 H5 Cg1 . 0.93 2.80 3.649(6) 151 yes O1 H1 N3 4_557 0.82 1.86 2.654(4) 162 yes N2 H2 O1 2_564 0.86 2.45 2.989(4) 121 yes N2 H2 N1 2_564 0.86 2.20 3.022(4) 160 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 N1 C1 C2 O1 1.2(6) C6 C1 C2 O1 180.0(3) N1 C1 C2 C3 -179.7(3) C6 C1 C2 C3 -0.9(6) O1 C2 C3 C4 -179.2(4) C1 C2 C3 C4 1.7(6) C2 C3 C4 C5 -0.9(7) C3 C4 C5 C6 -0.8(7) C4 C5 C6 C7 -177.9(4) C4 C5 C6 C1 1.6(6) N1 C1 C6 C5 178.0(4) C2 C1 C6 C5 -0.7(5) N1 C1 C6 C7 -2.5(5) C2 C1 C6 C7 178.8(4) C5 C6 C7 C8 -178.7(4) C1 C6 C7 C8 1.8(6) C6 C7 C8 C9 -0.6(7) C7 C8 C9 N1 0.0(7) N2 C10 C11 N3 0.5(4) C13 C10 C11 N3 179.7(4) C8 C9 N1 C1 -0.7(7) C2 C1 N1 C9 -179.3(4) C6 C1 N1 C9 2.0(6) N3 C12 N2 C10 -0.7(4) C11 C10 N2 C12 0.1(4) C13 C10 N2 C12 -179.2(4) N2 C12 N3 C11 1.0(4) C10 C11 N3 C12 -0.9(4) _cod_database_fobs_code 2208696