#------------------------------------------------------------------------------ #$Date: 2012-02-03 19:16:24 +0200 (Fri, 03 Feb 2012) $ #$Revision: 32112 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/01/53/2015340.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_2015340 loop_ _publ_author_name 'Lou, Ben-Yong' 'Huang, Xiao-Dong' 'Lin, Xiang-Chao' _publ_section_title ; The cocrystal of 3-hydroxy-2-naphthoic acid and 4,4'-bipyridine ; _journal_coeditor_code AV3011 _journal_issue 6 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first o310 _journal_page_last o311 _journal_volume 62 _journal_year 2006 _chemical_formula_moiety 'C11 H8 O3, 0.5C10 H8 N2' _chemical_formula_sum 'C16 H12 N O3' _chemical_formula_weight 266.27 _chemical_name_systematic ; 3-hydroxy-2-naphthoic--4,4'-bipyridine (2/1) ; _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' _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 98.799(12) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 8.999(5) _cell_length_b 11.735(7) _cell_length_c 12.393(7) _cell_measurement_reflns_used 2304 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 27.4372 _cell_measurement_theta_min 2.8736 _cell_volume 1293.3(13) _computing_cell_refinement CrystalClear _computing_data_collection 'CrystalClear (Rigaku Corporation, 2000)' _computing_data_reduction CrystalClear _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 293(2) _diffrn_detector_area_resol_mean 28.5714 _diffrn_measured_fraction_theta_full 0.994 _diffrn_measured_fraction_theta_max 0.994 _diffrn_measurement_device_type 'Make and Model?? CCD' _diffrn_measurement_method CCD_Profile_fitting _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 0.0422 _diffrn_reflns_av_sigmaI/netI 0.0401 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 9720 _diffrn_reflns_theta_full 27.44 _diffrn_reflns_theta_max 27.44 _diffrn_reflns_theta_min 2.29 _exptl_absorpt_coefficient_mu 0.095 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_correction_T_min 0.8210 _exptl_absorpt_correction_type multi-scan _exptl_crystal_colour Yellow _exptl_crystal_density_diffrn 1.367 _exptl_crystal_density_method 'not measured' _exptl_crystal_description Prism _exptl_crystal_F_000 556 _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.10 _refine_diff_density_max 0.266 _refine_diff_density_min -0.187 _refine_ls_extinction_coef 0.29(2) _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 0.963 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 182 _refine_ls_number_reflns 2934 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.963 _refine_ls_R_factor_all 0.0912 _refine_ls_R_factor_gt 0.0542 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0944P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1342 _refine_ls_wR_factor_ref 0.1581 _reflns_number_gt 1768 _reflns_number_total 2934 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file av3011.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M P21/c _cod_original_cell_volume 1293.4(13) _cod_database_code 2015340 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' 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_ _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 O O1 0.15570(12) 0.05389(12) 0.22487(10) 0.0717(4) Uani d . 1 H H1 0.0643 0.0462 0.1993 0.086 Uiso calc R 1 O O2 0.13676(15) 0.19441(15) 0.10344(14) 0.0983(5) Uani d . 1 O O3 0.37149(18) 0.30019(14) 0.06488(12) 0.0971(5) Uani d . 1 H H3 0.2812 0.2792 0.0545 0.117 Uiso calc R 1 N N1 -0.12165(14) 0.01352(13) 0.13242(11) 0.0588(4) Uani d . 1 C C1 0.21090(19) 0.13774(17) 0.17723(15) 0.0633(5) Uani d . 1 C C2 0.37275(17) 0.16406(15) 0.21240(14) 0.0552(4) Uani d . 1 C C3 0.4462(2) 0.24535(16) 0.15306(15) 0.0650(5) Uani d . 1 C C4 0.5967(2) 0.26847(18) 0.18401(17) 0.0754(6) Uani d . 1 H H4 0.6446 0.3225 0.1438 0.091 Uiso calc R 1 C C5 0.68033(19) 0.21370(17) 0.27386(16) 0.0685(5) Uani d . 1 C C6 0.8378(2) 0.2340(2) 0.3060(2) 0.0927(8) Uani d . 1 H H6 0.8886 0.2862 0.2657 0.111 Uiso calc R 1 C C7 0.9147(2) 0.1795(3) 0.3930(3) 0.1102(10) Uani d . 1 H H7 1.0195 0.1931 0.4122 0.132 Uiso calc R 1 C C8 0.8438(3) 0.1035(3) 0.4555(2) 0.1070(9) Uani d . 1 H H8 0.8992 0.0681 0.5180 0.128 Uiso calc R 1 C C9 0.6928(2) 0.0803(2) 0.42592(19) 0.0876(7) Uani d . 1 H H9 0.6451 0.0273 0.4675 0.105 Uiso calc R 1 C C10 0.60855(18) 0.13392(17) 0.33503(15) 0.0646(5) Uani d . 1 C C11 0.45347(18) 0.11116(16) 0.30113(14) 0.0598(5) Uani d . 1 H H11 0.4042 0.0577 0.3411 0.072 Uiso calc R 1 C C12 -0.16956(19) 0.07572(18) 0.04482(17) 0.0737(6) Uani d . 1 H H12 -0.1002 0.1252 0.0178 0.088 Uiso calc R 1 C C13 -0.31515(18) 0.07213(17) -0.00897(16) 0.0692(6) Uani d . 1 H H13 -0.3436 0.1184 -0.0716 0.083 Uiso calc R 1 C C14 -0.22045(19) -0.05580(17) 0.16810(16) 0.0684(5) Uani d . 1 H H14 -0.1881 -0.1016 0.2305 0.082 Uiso calc R 1 C C15 -0.36796(18) -0.06393(16) 0.11825(15) 0.0651(5) Uani d . 1 H H15 -0.4344 -0.1150 0.1464 0.078 Uiso calc R 1 C C16 -0.41996(15) 0.00183(13) 0.02734(12) 0.0482(4) Uani d . 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 O1 0.0449(6) 0.0862(10) 0.0820(9) -0.0066(6) 0.0032(6) 0.0061(7) O2 0.0602(8) 0.1003(12) 0.1237(12) -0.0072(7) -0.0199(8) 0.0347(9) O3 0.0899(10) 0.0976(12) 0.0998(11) -0.0135(9) 0.0014(8) 0.0287(9) N1 0.0444(7) 0.0642(10) 0.0676(9) -0.0032(6) 0.0076(6) -0.0012(7) C1 0.0491(9) 0.0667(12) 0.0718(11) 0.0013(8) 0.0014(8) -0.0057(9) C2 0.0463(8) 0.0570(10) 0.0619(10) -0.0009(7) 0.0075(8) -0.0119(8) C3 0.0635(10) 0.0634(12) 0.0676(11) -0.0022(9) 0.0079(9) -0.0051(9) C4 0.0646(11) 0.0727(13) 0.0929(14) -0.0166(10) 0.0246(11) -0.0134(11) C5 0.0488(9) 0.0717(12) 0.0854(13) -0.0056(8) 0.0114(9) -0.0300(10) C6 0.0530(11) 0.1053(19) 0.1207(18) -0.0148(11) 0.0157(12) -0.0519(15) C7 0.0480(11) 0.141(3) 0.135(2) 0.0041(14) -0.0056(14) -0.072(2) C8 0.0687(14) 0.133(2) 0.1091(19) 0.0320(15) -0.0187(14) -0.0380(17) C9 0.0679(12) 0.1027(18) 0.0863(15) 0.0162(11) -0.0076(11) -0.0147(12) C10 0.0494(9) 0.0725(13) 0.0699(11) 0.0058(8) 0.0022(8) -0.0215(9) C11 0.0479(8) 0.0653(11) 0.0658(11) -0.0008(8) 0.0074(8) -0.0056(8) C12 0.0465(9) 0.0862(14) 0.0858(14) -0.0163(9) 0.0021(9) 0.0195(11) C13 0.0504(9) 0.0788(14) 0.0761(12) -0.0127(8) 0.0023(8) 0.0242(9) C14 0.0519(9) 0.0785(13) 0.0722(12) -0.0030(9) 0.0010(8) 0.0154(9) C15 0.0484(8) 0.0729(12) 0.0738(12) -0.0094(8) 0.0083(8) 0.0166(9) C16 0.0414(7) 0.0500(9) 0.0540(9) -0.0021(6) 0.0103(6) -0.0049(7) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 C1 . 1.286(2) yes O1 H1 . 0.8400 ? O2 C1 . 1.240(2) yes O3 C3 . 1.355(2) yes O3 H3 . 0.8400 ? N1 C12 . 1.324(2) yes N1 C14 . 1.330(2) yes C1 C2 . 1.487(2) ? C2 C11 . 1.370(2) ? C2 C3 . 1.427(3) ? C3 C4 . 1.377(3) ? C4 C5 . 1.401(3) ? C4 H4 . 0.9500 ? C5 C10 . 1.421(3) ? C5 C6 . 1.432(3) ? C6 C7 . 1.350(4) ? C6 H6 . 0.9500 ? C7 C8 . 1.398(4) ? C7 H7 . 0.9500 ? C8 C9 . 1.379(3) ? C8 H8 . 0.9500 ? C9 C10 . 1.407(3) ? C9 H9 . 0.9500 ? C10 C11 . 1.420(2) ? C11 H11 . 0.9500 ? C12 C13 . 1.377(3) ? C12 H12 . 0.9500 ? C13 C16 . 1.379(2) ? C13 H13 . 0.9500 ? C14 C15 . 1.379(2) ? C14 H14 . 0.9500 ? C15 C16 . 1.387(2) ? C15 H15 . 0.9500 ? C16 C16 3_455 1.496(3) ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C1 O1 H1 . 109.5 ? C3 O3 H3 . 109.5 ? C12 N1 C14 . 117.34(14) yes O2 C1 O1 . 123.16(16) yes O2 C1 C2 . 119.81(17) yes O1 C1 C2 . 117.01(16) yes C11 C2 C3 . 119.08(15) ? C11 C2 C1 . 121.08(16) ? C3 C2 C1 . 119.84(16) ? O3 C3 C4 . 118.45(18) yes O3 C3 C2 . 121.45(16) ? C4 C3 C2 . 120.09(18) ? C3 C4 C5 . 121.13(19) ? C3 C4 H4 . 119.4 ? C5 C4 H4 . 119.4 ? C4 C5 C10 . 119.57(16) ? C4 C5 C6 . 122.2(2) ? C10 C5 C6 . 118.2(2) ? C7 C6 C5 . 120.5(2) ? C7 C6 H6 . 119.7 ? C5 C6 H6 . 119.7 ? C6 C7 C8 . 121.5(2) ? C6 C7 H7 . 119.2 ? C8 C7 H7 . 119.2 ? C9 C8 C7 . 119.6(3) ? C9 C8 H8 . 120.2 ? C7 C8 H8 . 120.2 ? C8 C9 C10 . 120.8(3) ? C8 C9 H9 . 119.6 ? C10 C9 H9 . 119.6 ? C9 C10 C11 . 122.5(2) ? C9 C10 C5 . 119.28(18) ? C11 C10 C5 . 118.21(18) ? C2 C11 C10 . 121.91(18) ? C2 C11 H11 . 119.0 ? C10 C11 H11 . 119.0 ? N1 C12 C13 . 123.12(16) ? N1 C12 H12 . 118.4 ? C13 C12 H12 . 118.4 ? C12 C13 C16 . 120.53(17) ? C12 C13 H13 . 119.7 ? C16 C13 H13 . 119.7 ? N1 C14 C15 . 122.69(17) ? N1 C14 H14 . 118.7 ? C15 C14 H14 . 118.7 ? C14 C15 C16 . 120.51(15) ? C14 C15 H15 . 119.7 ? C16 C15 H15 . 119.7 ? C13 C16 C15 . 115.80(14) ? C13 C16 C16 3_455 121.91(18) ? C15 C16 C16 3_455 122.29(17) ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA O1 H1 N1 0.84 1.79 2.625(2) 172 O3 H3 O2 0.84 1.81 2.557(2) 147