#------------------------------------------------------------------------------ #$Date: 2025-08-18 23:52:38 +0100 (Mon, 18 Aug 2025) $ #$Revision: 301791 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/85/2008567.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_2008567 loop_ _publ_author_name 'Dobson, Allison J.' 'Gerkin, Roger E.' _publ_section_title ; Hydrogen bonding in quinolinium-4-carboxylate dihydrate ; _journal_issue 6 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 935 _journal_page_last 937 _journal_paper_doi 10.1107/S0108270199002565 _journal_volume 55 _journal_year 1999 _chemical_formula_iupac 'C10 H7 N O2 , 2H2 O' _chemical_formula_moiety 'C10 H11 N1 O4' _chemical_formula_sum 'C10 H11 N O4' _chemical_formula_weight 209.20 _chemical_name_common 'quinolinium-4-carboxylate dihydrate ' _space_group_IT_number 9 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall 'C -2yc' _symmetry_space_group_name_H-M 'C 1 c 1' _cell_angle_alpha 90 _cell_angle_beta 117.38(2) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 8.438(2) _cell_length_b 27.4960(10) _cell_length_c 4.8940(10) _cell_measurement_reflns_used 25 _cell_measurement_temperature 296 _cell_measurement_theta_max 17.4 _cell_measurement_theta_min 15.6 _cell_volume 1008.3(4) _computing_cell_refinement 'MSC/AFC Diffractometer Control Software' _computing_data_collection ; MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1988) ; _computing_data_reduction 'TEXSAN (Molecular Structure Corporation, 1995)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material 'TEXSAN and PLATON (Spek, 1990)' _computing_structure_refinement TEXSAN _computing_structure_solution 'SHELXS86 (Sheldrick, 1985)' _diffrn_ambient_temperature 296 _diffrn_measurement_device AFC5S _diffrn_measurement_method '\w scans ' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'X-ray tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.026 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 35 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 5 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_number 1268 _diffrn_reflns_theta_max 27.53 _diffrn_reflns_theta_min 2.00 _diffrn_standards_decay_% '+-1.0 (average maximum relative intensity)' _diffrn_standards_interval_count 150 _diffrn_standards_number 6 _exptl_absorpt_coefficient_mu 0.108 _exptl_absorpt_correction_type none _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.378 _exptl_crystal_density_meas ? _exptl_crystal_description 'cut plate ' _exptl_crystal_F_000 440 _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.42 _exptl_crystal_size_min 0.19 _refine_diff_density_max 0.22 _refine_diff_density_min -0.17 _refine_ls_extinction_coef '1.6(2) \\times 10^-6^' _refine_ls_extinction_method 'Zachariasen, 1963, 1968' _refine_ls_goodness_of_fit_obs 1.85 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 155 _refine_ls_number_reflns 1239 _refine_ls_R_factor_gt 0.032 _refine_ls_shift/esd_max 0.0003 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/\s^2^(F^2^)' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_obs .055 _reflns_number_gt 1092 _reflns_number_total 1239 _reflns_threshold_expression 'I >2\s I' _cod_data_source_file fr1183.cif _cod_data_source_block quinolinium-4-carboxylate_dihydrate _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' 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: '_atom_site_thermal_displace_type' tag value 'Uij' was replaced with 'Uani' value 15 times. Automatic conversion script Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana The following automatic conversions were performed: '_exptl_crystal_density_meas' value 'none' was changed to '?' - the value is perceived as not measured. Automatic conversion script Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas The following automatic conversions were performed: '_refine_ls_weighting_scheme' value '1/\s^2^(F^2^)' was changed to 'calc'. New tag '_refine_ls_weighting_details' was created. The value of the new tag was set to 'w = 1/\s^2^(F^2^)'. Automatic conversion script Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas ; _cod_original_cell_volume 1008.3(3) _cod_original_sg_symbol_H-M 'C c' _cod_original_formula_sum 'C10 H11 N1 O4' _cod_database_code 2008567 loop_ _symmetry_equiv_pos_as_xyz x,y,z 'x, -y, 1/2 +z' '1/2 +x, 1/2 +y, z' '1/2 +x, 1/2 -y, 1/2 +z' 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 .0367(10) .0570(10) .0880(10) .0046(9) .0004(10) .0320(10) O2 .0231(8) .0427(9) .0640(10) -.0013(7) .0038(7) .0049(8) O3 .0580(10) .0600(10) .0410(10) .0080(10) .0120(10) .0022(9) O4 .092(2) .0510(10) .0660(10) .0100(10) .0480(10) .0090(10) N1 .0202(9) .0420(10) .0342(10) -.0018(8) .0040(8) .0026(8) C2 .0340(10) .0400(10) .0330(10) -.0060(10) .0088(10) -.0040(10) C3 .0310(10) .0380(10) .0370(10) .0019(10) .0120(10) -.0025(10) C4 .0230(10) .0320(10) .0320(10) -.0017(9) .0074(9) .0029(9) C5 .0340(10) .0390(10) .0330(10) -.0066(10) .0104(10) -.0017(10) C6 .049(2) .0410(10) .0440(10) -.0070(10) .0230(10) -.0070(10) C7 .048(2) .0400(10) .060(2) .0060(10) .0320(10) .0010(10) C8 .0290(10) .0460(10) .0490(10) .0060(10) .0170(10) .0070(10) C9 .0260(10) .0310(10) .0320(10) -.0007(9) .0099(9) .0050(9) C10 .0227(10) .0330(10) .0300(10) -.0027(8) .0085(9) .0041(8) C11 .0230(10) .0430(10) .0360(10) .0030(10) .0033(9) .0020(10) loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_calc_flag _atom_site_calc_attached_atom O1 .7734 .30121(7) 1.1653 .0713(6) Uani ? ? O2 .8234(3) .37548(6) 1.0489(6) .0494(5) Uani ? ? O3 1.0585(4) .27006(7) 1.7356(6) .0570(6) Uani ? ? O4 .7816(4) .47546(8) .8881(7) .0654(7) Uani ? ? N1 .1698(3) .35847(7) .4293(6) .0354(5) Uani ? ? C2 .2616(4) .32485(8) .3730(7) .0380(6) Uani ? ? C3 .4423(4) .31782(8) .5728(7) .0368(6) Uani ? ? C4 .5265(4) .34703(8) .8263(6) .0312(5) Uani ? ? C5 .4986(4) .41330(8) 1.1540(7) .0372(6) Uani ? ? C6 .3934(4) .44579(8) 1.2041(7) .0443(7) Uani ? ? C7 .2108(4) .44980(9) .9959(7) .0466(8) Uani ? ? C8 .1354(4) .42113(8) .7400(7) .0416(7) Uani ? ? C9 .2433(3) .38766(7) .6858(6) .0309(5) Uani ? ? C10 .4273(3) .38287(7) .8923(6) .0298(5) Uani ? ? C11 .7247(4) .34040(8) 1.0338(7) .0382(6) Uani ? ? H1 .048(3) .3627(8) .305(5) .060(8) Uiso ? ? H2 .2025 .3045 .1883 .0450 Uiso calc C2 H3 .5088 .2920 .5320 .0431 Uiso calc C3 H5 .6256 .4110 1.3008 .0437 Uiso calc C5 H6 .4450 .4666 1.3868 .0520 Uiso calc C6 H7 .1368 .4735 1.0354 .0549 Uiso calc C7 H8 .0076 .4239 .5962 .0489 Uiso calc C8 H9 .980(4) .2789(10) 1.571(7) .070(10) Uiso ? ? H10 1.124(5) .2470(10) 1.657(9) .130(10) Uiso ? ? H11 .782(6) .4440(10) .915(9) .130(10) Uiso ? ? H12 .774(5) .4890(10) 1.031(7) .090(10) Uiso ? ? loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source H 0 0 'Stewart et al. (1965)' C .003 .002 'Creagh & McAuley (1992)' N .006 .003 'Creagh & McAuley (1992)' O .011 .006 'Creagh & McAuley (1992)' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag H9 O3 H10 98(2) no H11 O4 H12 107(3) no C2 N1 C9 122.7(2) yes C2 N1 H1 122.0(10) no C9 N1 H1 115.0(10) no N1 C2 C3 120.7(2) no N1 C2 H2 119.7 no C3 C2 H2 119.7 no C2 C3 C4 119.8(2) no C2 C3 H3 120.0 no C4 C3 H3 120.1 no C3 C4 C10 119.8(2) no C3 C4 C11 119.3(2) yes C10 C4 C11 120.9(2) yes C6 C5 C10 120.8(2) no C6 C5 H5 119.6 no C10 C5 H5 119.6 no C5 C6 C7 120.6(2) no C5 C6 H6 119.8 no C7 C6 H6 119.6 no C6 C7 C8 120.8(2) no C6 C7 H7 119.6 no C8 C7 H7 119.6 no C7 C8 C9 118.9(2) no C7 C8 H8 120.5 no C9 C8 H8 120.6 no N1 C9 C8 119.8(2) no N1 C9 C10 118.9(2) no C8 C9 C10 121.3(2) no C4 C10 C5 124.5(2) no C4 C10 C9 117.9(2) no C5 C10 C9 117.5(2) no O1 C11 O2 126.4(2) yes O1 C11 C4 117.2(2) yes O2 C11 C4 116.4(2) yes loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 C11 ? ? 1.225(3) yes O2 C11 ? ? 1.254(3) yes O3 H9 ? ? .81(3) no O3 H10 ? ? 1.03(4) no O4 H11 ? ? .87(3) no O4 H12 ? ? .82(3) no N1 C2 ? ? 1.314(3) no N1 C9 ? ? 1.374(3) no N1 H1 ? ? .93(2) no C2 C3 ? ? 1.396(3) no C2 H2 ? ? .981 no C3 C4 ? ? 1.370(3) no C3 H3 ? ? .981 no C4 C10 ? ? 1.423(3) no C4 C11 ? ? 1.516(3) no C5 C6 ? ? 1.359(3) no C5 C10 ? ? 1.412(3) no C5 H5 ? ? .980 no C6 C7 ? ? 1.407(3) no C6 H6 ? ? .979 no C7 C8 ? ? 1.365(3) no C7 H7 ? ? .980 no C8 C9 ? ? 1.403(3) no C8 H8 ? ? .982 no C9 C10 ? ? 1.416(3) no 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 N1 H1 O2 1_454 0.93(2) 1.76(3) 2.688(2) 174(2) yes O3 H9 O1 ? 0.81(3) 2.04(3) 2.852(3) 177(3) yes O3 H10 O1 4_555 1.03(4) 1.81(4) 2.797(3) 159(3) yes O4 H11 O2 ? 0.87(3) 1.98(3) 2.837(2) 169(4) yes O4 H12 O4 2_565 0.82(3) 1.98(3) 2.794(2) 173(4) yes C2 H2 O3 1_453 0.98 2.19 3.165(3) 171 yes C3 H3 O3 4_453 0.98 2.40 3.318(3) 156 yes loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 139056614