#------------------------------------------------------------------------------ #$Date: 2016-02-14 14:26:36 +0000 (Sun, 14 Feb 2016) $ #$Revision: 176435 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/89/2008903.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_2008903 loop_ _publ_author_name 'Dobson, Allison J.' 'Gerkin, Roger E.' _publ_section_title ; Hydrogen bonding and C---H···X interactions in two triclinic phases of 4-carboxyquinolinium chloride monohydrate ; _journal_issue 9 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 1499 _journal_page_last 1503 _journal_paper_doi 10.1107/S0108270199006885 _journal_volume 55 _journal_year 1999 _chemical_formula_moiety 'C10 H8 N1 O2 + , Cl - , H2 O ' _chemical_formula_sum 'C10 H10 Cl N O3' _chemical_formula_weight 227.65 _chemical_name_common 'quinolinium-4-carboxylic acid chloride monohydrate ' _chemical_name_systematic ' ?' _space_group_IT_number 2 _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _cell_angle_alpha 84.250(10) _cell_angle_beta 77.380(10) _cell_angle_gamma 61.020(10) _cell_formula_units_Z 2 _cell_length_a 7.7400(10) _cell_length_b 7.948(2) _cell_length_c 9.9840(10) _cell_measurement_reflns_used 25 _cell_measurement_temperature 296 _cell_measurement_theta_max 17.4 _cell_measurement_theta_min 14.3 _cell_volume 524.30(17) _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 'Rigaku AFC-5S' _diffrn_measurement_method '\w/2\q 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 0.011 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 2594 _diffrn_reflns_theta_max 27.56 _diffrn_reflns_theta_min 2.00 _diffrn_standards_decay_% '+- 1.2 (average maximum relative intensity)' _diffrn_standards_interval_count 150 _diffrn_standards_number 6 _exptl_absorpt_coefficient_mu 0.35 _exptl_absorpt_correction_type none _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.442 _exptl_crystal_density_meas ? _exptl_crystal_description 'irregular hexagonal column ' _exptl_crystal_F_000 236 _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.35 _refine_diff_density_max 0.43 _refine_diff_density_min -0.33 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.93 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 152 _refine_ls_number_reflns 2420 _refine_ls_R_factor_gt 0.039 _refine_ls_shift/su_max <0.001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^~cs~ + (0.003 I)^2^]' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref 0.096 _reflns_number_gt 1913 _reflns_number_total 2420 _reflns_threshold_expression I>2\s(I) _cod_data_source_file fr1208.cif _cod_data_source_block Ia _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic' 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: '_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic' 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 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^~cs~ + (0.003 I)^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^~cs~ + (0.003 I)^2^]'. Automatic conversion script Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas ; _cod_original_cell_volume 524.30(10) _cod_original_formula_sum 'C10 H10 Cl1 N1 O3' _cod_database_code 2008903 loop_ _symmetry_equiv_pos_as_xyz x,y,z '-x, -y, -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 Cl1 0.0644(3) 0.0748(3) 0.0512(3) -0.0535(3) -0.0027(2) -0.0050(2) O1 0.1000(10) 0.0910(10) 0.0577(8) -0.0770(10) -0.0009(8) -0.0181(8) O2 0.0920(10) 0.0767(10) 0.0606(8) -0.0681(9) 0.0086(7) -0.0098(7) O3 0.121(2) 0.1080(10) 0.0650(10) -0.0970(10) -0.0280(10) 0.0105(10) N1 0.0422(8) 0.0450(8) 0.0471(8) -0.0304(7) -0.0030(6) 0.0002(6) C2 0.0462(10) 0.0530(10) 0.0447(9) -0.0302(9) 0.0052(7) -0.0060(8) C3 0.0510(10) 0.0490(10) 0.0437(9) -0.0304(9) 0.0016(8) -0.0108(8) C4 0.0405(8) 0.0374(8) 0.0392(8) -0.0244(7) -0.0071(7) -0.0006(7) C5 0.0342(8) 0.0397(9) 0.0427(8) -0.0203(7) -0.0042(7) -0.0010(7) C6 0.0376(9) 0.0416(9) 0.0442(9) -0.0152(8) -0.0027(7) -0.0053(7) C7 0.0490(10) 0.0378(9) 0.0530(10) -0.0187(8) -0.0102(8) -0.0103(8) C8 0.0467(10) 0.0380(9) 0.0544(10) -0.0262(8) -0.0120(8) -0.0023(8) C9 0.0349(8) 0.0340(8) 0.0385(8) -0.0195(7) -0.0080(6) 0.0028(6) C10 0.0345(8) 0.0324(8) 0.0356(8) -0.0187(7) -0.0074(6) 0.0020(6) C11 0.0451(10) 0.0398(9) 0.0498(10) -0.0269(8) -0.0059(8) -0.0033(7) 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 Cl1 0.43358(7) 0.29634(7) -0.33088(5) 0.0557(2) Uani ? ? O1 -0.1538(3) -0.2608(2) -0.36260(10) 0.0700(5) Uani ? ? O2 -0.2715(2) -0.2107(2) -0.13930(10) 0.0674(5) Uani ? ? O3 0.6855(3) 0.5250(3) -0.3876(2) 0.0787(7) Uani ? ? N1 0.1589(2) 0.1122(2) -0.28120(10) 0.0415(4) Uani ? ? C2 0.2115(3) -0.0245(3) -0.3699(2) 0.0469(5) Uani ? ? C3 0.0990(3) -0.1205(3) -0.3593(2) 0.0456(5) Uani ? ? C4 -0.0666(2) -0.0728(2) -0.2559(2) 0.0365(4) Uani ? ? C5 -0.2917(2) 0.1370(2) -0.0487(2) 0.0381(4) Uani ? ? C6 -0.3308(2) 0.2789(2) 0.0368(2) 0.0431(5) Uani ? ? C7 -0.2105(3) 0.3694(2) 0.0181(2) 0.0466(5) Uani ? ? C8 -0.0486(3) 0.3156(2) -0.0875(2) 0.0431(5) Uani ? ? C9 -0.0052(2) 0.1682(2) -0.1760(2) 0.0345(4) Uani ? ? C10 -0.1236(2) 0.0742(2) -0.15970(10) 0.0329(4) Uani ? ? C11 -0.1792(3) -0.1861(2) -0.2446(2) 0.0422(5) Uani ? ? H1 0.240(3) 0.177(3) -0.293(2) 0.071(6) Uiso ? ? H2 0.3301 -0.0586 -0.4436 0.0563 Uiso calc C2 H3 0.1380 -0.2219 -0.4254 0.0547 Uiso calc C3 H5 -0.3796 0.0776 -0.0339 0.0457 Uiso calc C5 H6 -0.4460 0.3191 0.1136 0.0517 Uiso calc C6 H7 -0.2431 0.4720 0.0813 0.0559 Uiso calc C7 H8 0.0357 0.3788 -0.1012 0.0517 Uiso calc C8 H9 -0.199(4) -0.343(4) -0.351(3) 0.109(10) Uiso ? ? H10 0.632(4) 0.464(4) -0.355(3) 0.081(8) Uiso ? ? H11 0.653(4) 0.564(4) -0.462(3) 0.090(9) 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)' Cl .148 .159 '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 C11 O1 H9 110.0(10) no H10 O3 H11 107(2) yes C2 N1 C9 123.20(10) yes C2 N1 H1 117.0(10) no C9 N1 H1 119.0(10) no N1 C2 C3 120.2(2) no N1 C2 H2 119.9 no C3 C2 H2 119.9 no C2 C3 C4 119.8(2) no C2 C3 H3 120.1 no C4 C3 H3 120.1 no C3 C4 C10 120.20(10) no C3 C4 C11 118.00(10) yes C10 C4 C11 121.70(10) yes C6 C5 C10 120.20(10) no C6 C5 H5 119.9 no C10 C5 H5 119.9 no C5 C6 C7 121.7(2) no C5 C6 H6 119.1 no C7 C6 H6 119.1 no C6 C7 C8 120.4(2) no C6 C7 H7 119.8 no C8 C7 H7 119.8 no C7 C8 C9 118.60(10) no C7 C8 H8 120.7 no C9 C8 H8 120.7 no N1 C9 C8 118.70(10) no N1 C9 C10 119.00(10) no C8 C9 C10 122.30(10) no C4 C10 C5 125.60(10) no C4 C10 C9 117.60(10) no C5 C10 C9 116.80(10) no O1 C11 O2 124.7(2) yes O1 C11 C4 111.60(10) yes O2 C11 C4 123.6(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 ? ? 1.306(2) yes O1 H9 ? ? 0.86(3) no O2 C11 ? ? 1.192(2) yes O3 H10 ? ? 0.78(3) no O3 H11 ? ? 0.82(3) no N1 C2 ? ? 1.319(2) yes N1 C9 ? ? 1.370(2) yes N1 H1 ? ? 0.97(2) no C2 C3 ? ? 1.393(2) no C2 H2 ? ? 0.980 no C3 C4 ? ? 1.371(2) no C3 H3 ? ? 0.980 no C4 C10 ? ? 1.422(2) no C4 C11 ? ? 1.510(2) no C5 C6 ? ? 1.357(2) no C5 C10 ? ? 1.422(2) no C5 H5 ? ? 0.980 no C6 C7 ? ? 1.401(2) no C6 H6 ? ? 0.980 no C7 C8 ? ? 1.363(2) no C7 H7 ? ? 0.980 no C8 C9 ? ? 1.401(2) no C8 H8 ? ? 0.980 no C9 C10 ? ? 1.413(2) 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 Cl1 ? 0.97(2) 2.08(2) 3.0520(10) 175(2) yes O1 H9 O3 1_445 0.86(3) 1.78(3) 2.603(3) 158(3) yes O3 H10 Cl1 ? 0.78(3) 2.44(3) 3.189(2) 161(2) yes O3 H11 Cl1 2_664 0.82(3) 2.32(3) 3.135(2) 174(2) yes C2 H2 Cl1 2_654 0.98 2.77 3.619(2) 145 yes C3 H3 O3 2_654 0.98 2.78 3.754(2) 170 yes C5 H5 O2 2_455 0.98 2.64 3.290(2) 124 yes C6 H6 O2 2_455 0.98 2.67 3.308(2) 123 yes C7 H7 Cl1 2_565 0.98 2.91 3.828(2) 157 yes