#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:43:10 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301803 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/00/2200033.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_2200033 loop_ _publ_author_name 'Slouf, Miroslav' _publ_section_title ; 3-Carboxypyridinium chloride ; _journal_issue 1 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o61 _journal_page_last o62 _journal_paper_doi 10.1107/S1600536800019632 _journal_volume 57 _journal_year 2001 _chemical_formula_iupac 'C6 H6 O2 N1 1+, Cl1 1-' _chemical_formula_moiety 'C6 H6 O2 N1 1+, Cl1 1-' _chemical_formula_sum 'C6 H6 Cl N O2' _chemical_formula_weight 159.57 _chemical_name_common '3-carboxypyridinium chloride' _chemical_name_systematic ; 3-carboxypyridinium chloride ; _space_group_IT_number 11 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yb' _symmetry_space_group_name_H-M 'P 1 21/m 1' _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 99.555(5) _cell_angle_gamma 90.00 _cell_formula_units_Z 2 _cell_length_a 7.1704(3) _cell_length_b 6.6685(6) _cell_length_c 7.4937(6) _cell_measurement_reflns_used 2406 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 25 _cell_measurement_theta_min 1 _cell_volume 353.35(5) _computing_cell_refinement 'HKL SCALEPACK (Otwinowski & Minor, 1997)' _computing_data_collection 'COLLECT (Nonius, 1995)' _computing_data_reduction ; HKL DENZO and SCALEPACK (Otwinowski & Minor, 1997) and JANA2000 (Petricek & Dusek, 2000) ; _computing_molecular_graphics 'PLATON (Spek, 1990)' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _diffrn_ambient_temperature 293(2) _diffrn_detector_area_resol_mean .110 _diffrn_measured_fraction_theta_full .999 _diffrn_measured_fraction_theta_max .999 _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method '\f and \w' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength .71070 _diffrn_reflns_av_R_equivalents .015 _diffrn_reflns_av_sigmaI/netI .030 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 2406 _diffrn_reflns_theta_full 25.0 _diffrn_reflns_theta_max 25.0 _diffrn_reflns_theta_min 2.76 _diffrn_standards_decay_% 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu .47 _exptl_absorpt_correction_type none _exptl_crystal_colour 'translucent colourless' _exptl_crystal_density_diffrn 1.500 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 164 _exptl_crystal_size_max .3 _exptl_crystal_size_mid .2 _exptl_crystal_size_min .2 _refine_diff_density_max .21 _refine_diff_density_min -.22 _refine_ls_extinction_coef .090(17) _refine_ls_extinction_method SHELXL97 _refine_ls_goodness_of_fit_ref 1.11 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 80 _refine_ls_number_reflns 679 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.11 _refine_ls_R_factor_all .036 _refine_ls_R_factor_gt .031 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean <0.001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0263P)^2^+0.1615P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .077 _reflns_number_gt 608 _reflns_number_total 679 _reflns_threshold_expression I>2\s(I) _cod_data_source_file cf6022.cif _cod_data_source_block I _cod_original_sg_symbol_H-M 'P 21/m' _cod_original_formula_sum 'C6 H6 Cl1 N1 O2' _cod_database_code 2200033 _cod_database_fobs_code 2200033 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' '-x, -y, -z' 'x, -y-1/2, z' loop_ _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 _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol Cl1 .71876(9) .2500 .14792(8) .0409(3) Uani d S 1 . . Cl O1 .5551(2) .2500 .4790(2) .0510(6) Uani d S 1 . . O O2 .2816(3) .2500 .2907(2) .0765(9) Uani d S 1 . . O C7 .3704(4) .2500 .4408(3) .0427(7) Uani d S 1 . . C C1 .2747(3) .2500 .6036(3) .0350(6) Uani d S 1 . . C C2 .3771(4) .2500 .7746(3) .0353(6) Uani d S 1 . . C N3 .2875(3) .2500 .9170(3) .0369(6) Uani d S 1 . . N C4 .1005(4) .2500 .9007(4) .0443(7) Uani d S 1 . . C C5 -.0081(4) .2500 .7323(4) .0501(8) Uani d S 1 . . C C6 .0793(4) .2500 .5825(4) .0437(7) Uani d S 1 . . C H1 .610(6) .2500 .363(6) .093(13) Uiso d S 1 . . H H2 .505(4) .2500 .801(3) .038(7) Uiso d S 1 . . H H3 .359(4) .2500 1.022(4) .050(9) Uiso d S 1 . . H H4 .050(4) .2500 1.006(4) .047(8) Uiso d S 1 . . H H5 -.139(5) .2500 .728(4) .059(9) Uiso d S 1 . . H H6 .012(4) .2500 .470(4) .046(8) Uiso d S 1 . . H 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 .0355(4) .0539(5) .0344(4) .000 .0089(3) .000 O1 .0328(11) .0905(17) .0301(10) .000 .0065(8) .000 O2 .0413(12) .166(3) .0220(10) .000 .0035(8) .000 C7 .0375(15) .0633(19) .0271(13) .000 .0052(11) .000 C1 .0328(13) .0470(17) .0250(12) .000 .0038(10) .000 C2 .0309(14) .0467(17) .0281(13) .000 .0047(10) .000 N3 .0394(13) .0475(14) .0229(11) .000 .0022(9) .000 C4 .0438(16) .0583(19) .0340(15) .000 .0161(12) .000 C5 .0311(15) .079(2) .0407(16) .000 .0086(12) .000 C6 .0350(14) .065(2) .0290(14) .000 -.0007(11) .000 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl .1484 .1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O .0106 .0060 '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 _geom_angle_publ_flag O2 C7 O1 124.5(2) yes C7 O1 H1 110(2) yes O2 C7 C1 121.5(2) yes O1 C7 C1 114.0(2) yes C2 C1 C6 118.9(2) no C2 C1 C7 121.1(2) no C6 C1 C7 120.0(2) no N3 C2 C1 119.6(2) no N3 C2 H2 115.5(17) no C1 C2 H2 124.8(17) no C4 N3 C2 122.7(2) no C4 N3 H3 121(2) no C2 N3 H3 116(2) no N3 C4 C5 119.8(2) no N3 C4 H4 117.2(18) no C5 C4 H4 123.0(18) no C4 C5 C6 119.1(3) no C4 C5 H5 116.7(19) no C6 C5 H5 124.2(19) no C5 C6 C1 119.8(2) no C5 C6 H6 121.1(18) no C1 C6 H6 119.0(18) no 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 C7 . 1.308(3) yes O2 C7 . 1.197(3) yes C7 C1 . 1.496(3) yes C1 C2 . 1.367(3) yes C1 C6 . 1.383(4) yes C2 N3 . 1.333(3) yes N3 C4 . 1.326(4) yes C4 C5 . 1.369(4) yes C5 C6 . 1.373(4) yes O1 H1 . 1.01(4) yes C2 H2 . .91(3) yes N3 H3 . .86(3) yes C4 H4 . .92(3) yes C5 H5 . .93(3) yes C6 H6 . .90(3) yes 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 O1 H1 Cl1 . 1.01(4) 1.90(4) 2.9154(19) 179.0(10) yes N3 H3 O2 1_556 .86(3) 2.18(3) 2.808(3) 130(3) yes N3 H3 Cl1 1_556 .86(3) 2.60(3) 3.283(2) 137(3) yes loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 64631 2 PubChem 11217403