#------------------------------------------------------------------------------ #$Date: 2011-09-28 17:24:46 +0300 (Wed, 28 Sep 2011) $ #$Revision: 26848 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/01/53/2015386.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_2015386 loop_ _publ_author_name 'Janet M. S. Skakle' 'James L. Wardell' 'Solange M. S. V. Wardell' _publ_section_title ; Formation of ladders from R~4~^4^(8) and R~6~^6^(12) rings in 8-hydroxyquinolinium chloride monohydrate: comparisons with the supramolecular arrangements in related salts ; _journal_coeditor_code SK3016 _journal_issue 6 _journal_name_full 'Acta Crystallographica, Section C' _journal_page_first o312 _journal_page_last o314 _journal_volume 62 _journal_year 2006 _chemical_formula_iupac 'C9 H8 N O +, Cl -, H2 O' _chemical_formula_moiety 'C9 H8 N O +, Cl -, H2 O' _chemical_formula_sum 'C9 H10 Cl N O2' _chemical_formula_weight 199.63 _chemical_name_systematic ; 8-hydroxyquinolinium chloride monohydrate ; _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_hydrogens difmap _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 78.328(2) _cell_angle_beta 86.105(2) _cell_angle_gamma 66.388(2) _cell_formula_units_Z 2 _cell_length_a 7.2865(3) _cell_length_b 8.2885(4) _cell_length_c 8.4596(3) _cell_measurement_reflns_used 2046 _cell_measurement_temperature 120(2) _cell_measurement_theta_max 27.48 _cell_measurement_theta_min 2.91 _cell_volume 458.41(3) _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) and COLLECT' _computing_data_collection 'COLLECT (Hooft, 1998)' _computing_data_reduction ; DENZO and COLLECT ; _computing_molecular_graphics ; ORTEP-3 for Windows (Farrugia, 1997) ; _computing_publication_material SHELXL97 _computing_structure_refinement ; OSCAIL and SHELXL97 (Sheldrick, 1997) ; _computing_structure_solution ; OSCAIL (McArdle, 2003) and SHELXS97 (Sheldrick, 1997) ; _diffrn_ambient_temperature 120(2) _diffrn_detector_area_resol_mean 9.091 _diffrn_measured_fraction_theta_full 0.994 _diffrn_measured_fraction_theta_max 0.994 _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method '\f and \w' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'Bruker--Nonius FR591 rotating anode' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0305 _diffrn_reflns_av_sigmaI/netI 0.0286 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_number 9570 _diffrn_reflns_theta_full 27.53 _diffrn_reflns_theta_max 27.53 _diffrn_reflns_theta_min 3.72 _diffrn_standards_decay_% 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.381 _exptl_absorpt_correction_T_max 0.92813 _exptl_absorpt_correction_T_min 0.80147 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 2003)' _exptl_crystal_colour 'light orange' _exptl_crystal_density_diffrn 1.446 _exptl_crystal_density_method 'not measured' _exptl_crystal_description shard _exptl_crystal_F_000 208 _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.14 _refine_diff_density_max 0.323 _refine_diff_density_min -0.281 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.143 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 131 _refine_ls_number_reflns 2098 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.143 _refine_ls_R_factor_all 0.0400 _refine_ls_R_factor_gt 0.0326 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0351P)^2^+0.18P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0814 _refine_ls_wR_factor_ref 0.0852 _reflns_number_gt 1835 _reflns_number_total 2098 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file sk3016.cif loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' 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' Cl Cl 0.1484 0.1585 '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 Cl Cl1 0.17820(5) 0.10183(5) -0.36696(4) 0.02224(13) Uani d . 1 N N1 0.82589(18) 0.25417(18) 0.16555(14) 0.0184(3) Uani d . 1 H H1 0.833(3) 0.143(3) 0.172(2) 0.039(6) Uiso d . 1 C C2 0.8616(2) 0.3020(2) 0.29698(17) 0.0215(3) Uani d . 1 H H2 0.8999 0.2165 0.3949 0.026 Uiso calc R 1 C C3 0.8431(2) 0.4769(2) 0.29222(18) 0.0234(3) Uani d . 1 H H3 0.8704 0.5106 0.3860 0.028 Uiso calc R 1 C C4 0.7853(2) 0.5996(2) 0.15110(18) 0.0212(3) Uani d . 1 H H4 0.7713 0.7193 0.1475 0.025 Uiso calc R 1 C C4A 0.7462(2) 0.55025(19) 0.01067(17) 0.0179(3) Uani d . 1 C C5 0.6851(2) 0.6717(2) -0.13813(18) 0.0223(3) Uani d . 1 H H5 0.6664 0.7934 -0.1472 0.027 Uiso calc R 1 C C6 0.6533(2) 0.6117(2) -0.26893(18) 0.0240(3) Uani d . 1 H H6 0.6134 0.6932 -0.3690 0.029 Uiso calc R 1 C C7 0.6781(2) 0.4328(2) -0.25901(17) 0.0208(3) Uani d . 1 H H7 0.6563 0.3952 -0.3524 0.025 Uiso calc R 1 C C8 0.7336(2) 0.3114(2) -0.11544(17) 0.0178(3) Uani d . 1 O O1 0.75513(17) 0.13843(14) -0.09175(12) 0.0227(2) Uani d . 1 H H1A 0.7184 0.1190 -0.1754 0.034 Uiso calc R 1 C C8A 0.7695(2) 0.37084(19) 0.02019(16) 0.0163(3) Uani d . 1 O O1W 0.6131(2) 0.09370(16) -0.35024(14) 0.0260(3) Uani d . 1 H H1WA 0.674(3) 0.041(3) -0.423(3) 0.043(6) Uiso d . 1 H H1WB 0.505(4) 0.091(3) -0.349(3) 0.043(6) Uiso 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 Cl1 0.0263(2) 0.0219(2) 0.01917(19) -0.00936(15) -0.00190(13) -0.00486(14) N1 0.0183(6) 0.0197(7) 0.0182(6) -0.0084(5) -0.0022(5) -0.0028(5) C2 0.0191(7) 0.0288(8) 0.0171(7) -0.0101(6) -0.0026(5) -0.0031(6) C3 0.0207(8) 0.0329(9) 0.0230(7) -0.0136(7) 0.0007(6) -0.0130(6) C4 0.0180(7) 0.0221(8) 0.0277(8) -0.0095(6) 0.0037(6) -0.0113(6) C4A 0.0131(7) 0.0186(7) 0.0222(7) -0.0061(6) 0.0026(5) -0.0055(6) C5 0.0202(7) 0.0170(7) 0.0273(8) -0.0069(6) 0.0026(6) -0.0008(6) C6 0.0203(8) 0.0256(8) 0.0205(7) -0.0068(7) 0.0008(6) 0.0030(6) C7 0.0186(7) 0.0272(8) 0.0165(7) -0.0087(6) 0.0008(5) -0.0049(6) C8 0.0158(7) 0.0195(7) 0.0188(7) -0.0070(6) 0.0018(5) -0.0055(6) O1 0.0312(6) 0.0206(6) 0.0196(5) -0.0124(5) -0.0035(4) -0.0050(4) C8A 0.0146(7) 0.0184(7) 0.0159(7) -0.0068(6) 0.0005(5) -0.0029(5) O1W 0.0280(7) 0.0319(7) 0.0230(6) -0.0135(5) 0.0003(5) -0.0121(5) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance N1 C2 1.3272(19) N1 C8A 1.3730(18) N1 H1 0.89(2) C2 C3 1.394(2) C2 H2 0.9500 C3 C4 1.368(2) C3 H3 0.9500 C4 C4A 1.412(2) C4 H4 0.9500 C4A C8A 1.413(2) C4A C5 1.414(2) C5 C6 1.369(2) C5 H5 0.9500 C6 C7 1.405(2) C6 H6 0.9500 C7 C8 1.377(2) C7 H7 0.9500 C8 O1 1.3525(18) C8 C8A 1.414(2) O1 H1A 0.8400 O1W H1WA 0.82(2) O1W H1WB 0.79(2) loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C2 N1 C8A 122.87(14) C2 N1 H1 119.1(13) C8A N1 H1 118.0(13) N1 C2 C3 120.43(14) N1 C2 H2 119.8 C3 C2 H2 119.8 C4 C3 C2 119.31(14) C4 C3 H3 120.3 C2 C3 H3 120.3 C3 C4 C4A 120.72(14) C3 C4 H4 119.6 C4A C4 H4 119.6 C4 C4A C8A 118.13(13) C4 C4A C5 123.11(14) C8A C4A C5 118.76(13) C6 C5 C4A 119.23(14) C6 C5 H5 120.4 C4A C5 H5 120.4 C5 C6 C7 121.75(14) C5 C6 H6 119.1 C7 C6 H6 119.1 C8 C7 C6 120.73(14) C8 C7 H7 119.6 C6 C7 H7 119.6 O1 C8 C7 125.40(13) O1 C8 C8A 116.44(12) C7 C8 C8A 118.16(14) C8 O1 H1A 109.5 N1 C8A C4A 118.54(13) N1 C8A C8 120.10(13) C4A C8A C8 121.36(13) H1WA O1W H1WB 105(2) 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 C8A N1 C2 C3 -0.1(2) N1 C2 C3 C4 0.8(2) C2 C3 C4 C4A -0.6(2) C3 C4 C4A C8A -0.3(2) C3 C4 C4A C5 179.67(14) C4 C4A C5 C6 179.05(14) C8A C4A C5 C6 -1.0(2) C4A C5 C6 C7 0.5(2) C5 C6 C7 C8 0.7(2) C6 C7 C8 O1 177.72(13) C6 C7 C8 C8A -1.5(2) C2 N1 C8A C4A -0.8(2) C2 N1 C8A C8 -179.98(13) C4 C4A C8A N1 1.0(2) C5 C4A C8A N1 -179.01(12) C4 C4A C8A C8 -179.83(13) C5 C4A C8A C8 0.2(2) O1 C8 C8A N1 0.9(2) C7 C8 C8A N1 -179.78(13) O1 C8 C8A C4A -178.25(12) C7 C8 C8A C4A 1.0(2) 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 O1 H1A O1W . 0.84 1.80 2.6329(15) 173.9 N1 H1 O1 . 0.89(2) 2.35(2) 2.7050(16) 103.7(15) N1 H1 Cl1 2_655 0.89(2) 2.37(2) 3.1048(13) 140.2(17) O1W H1WA Cl1 2_654 0.82(2) 2.30(3) 3.1245(13) 176(2) O1W H1WB Cl1 . 0.79(2) 2.36(3) 3.1550(14) 175(2) _cod_database_code 2015386