#------------------------------------------------------------------------------
#$Date: 2025-08-22 14:50:14 +0200 (Fri, 22 Aug 2025) $
#$Revision: 301863 $
#$URL: svn://saulius.grazulis.lt/cod-secondary/cif/7/20/47/7204729.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7204729
loop_
_publ_author_name
'Kalle I. N\"attinen'
'Kari Rissanen'
_publ_section_title
;
 Chloride--hydrogen interactions of picolinic, nicotinic and
 isonicotinic acid chloride hydrochlorides in the crystalline state
;
_journal_issue                   57
_journal_name_full               CrystEngComm
_journal_page_first              326
_journal_page_last               330
_journal_paper_doi               10.1039/b307875b
_journal_volume                  5
_journal_year                    2003
_chemical_formula_sum            'C6 H5 Cl2 N O'
_chemical_formula_weight         178.01
_chemical_name_common            '2-Chlorocarboxypyridinium Chloride'
_chemical_name_systematic        '2-Chlorocarboxypyridinium Chloride'
_space_group_IT_number           62
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      62
_symmetry_space_group_name_Hall  '-P 2bc 2a'
_symmetry_space_group_name_H-M   'P m n b'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.358(2)
_cell_length_b                   8.744(3)
_cell_length_c                   13.594(7)
_cell_measurement_reflns_used    763
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.028
_cell_measurement_theta_min      2.91
_cell_volume                     755.7(5)
_computing_cell_refinement       DENZO-SMN
_computing_data_collection       Collect
_computing_data_reduction        DENZO-SMN
_computing_molecular_graphics    Platon
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'Rotations in phi and omega, 2 deg.'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0103
_diffrn_reflns_av_sigmaI/netI    0.0242
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            1253
_diffrn_reflns_theta_full        25.04
_diffrn_reflns_theta_max         25.04
_diffrn_reflns_theta_min         3.00
_exptl_absorpt_coefficient_mu    0.783
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.565
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Needless
_exptl_crystal_F_000             360
_exptl_crystal_size_max          1.10
_exptl_crystal_size_mid          0.80
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.233
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     61
_refine_ls_number_reflns         725
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0324
_refine_ls_R_factor_gt           0.0308
_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^)+(0.0242P)^2^+0.7501P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0758
_refine_ls_wR_factor_ref         0.0767
_reflns_number_gt                686
_reflns_number_total             725
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b307875b.txt
_cod_data_source_block           1a
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
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 
;
_cod_original_sg_symbol_H-M      Pmnb
_cod_database_code               7204729
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y+1/2, z+1/2'
'x+1/2, -y, -z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, y-1/2, -z-1/2'
'-x-1/2, y, z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C2 C 0.2500 0.4044(3) 0.3685(2) 0.0311(6) Uani 1 2 d S . .
C4 C 0.2500 0.2898(3) 0.45008(19) 0.0239(6) Uani 1 2 d S . .
C6 C 0.2500 0.2667(4) 0.6217(2) 0.0327(7) Uani 1 2 d S . .
H6 H 0.2500 0.3207 0.6931 0.039 Uiso 1 2 calc SR . .
C7 C 0.2500 0.1091(4) 0.6149(2) 0.0362(7) Uani 1 2 d S . .
H7 H 0.2500 0.0392 0.6804 0.043 Uiso 1 2 calc SR . .
C8 C 0.2500 0.0432(3) 0.5233(2) 0.0341(7) Uani 1 2 d S . .
H8 H 0.2500 -0.0799 0.5163 0.041 Uiso 1 2 calc SR . .
C9 C 0.2500 0.1339(3) 0.4393(2) 0.0305(6) Uani 1 2 d S . .
H9 H 0.2500 0.0827 0.3670 0.037 Uiso 1 2 calc SR . .
N5 N 0.2500 0.3526(2) 0.54093(16) 0.0252(5) Uani 1 2 d S . .
H5 H 0.2500 0.4665 0.5476 0.030 Uiso 1 2 calc SR . .
O3 O 0.2500 0.5382(2) 0.38149(16) 0.0454(6) Uani 1 2 d S . .
Cl1 Cl 0.2500 0.32469(9) 0.25026(5) 0.0400(3) Uani 1 2 d S . .
Cl10 Cl 0.2500 0.67010(7) 0.62096(5) 0.0305(2) Uani 1 2 d S . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C2 0.0360(16) 0.0329(16) 0.0243(14) 0.0028(12) 0.000 0.000
C4 0.0215(12) 0.0263(13) 0.0238(13) 0.0019(11) 0.000 0.000
C6 0.0357(16) 0.0383(16) 0.0241(14) 0.0037(12) 0.000 0.000
C7 0.0338(16) 0.0362(16) 0.0386(17) 0.0135(13) 0.000 0.000
C8 0.0267(14) 0.0243(13) 0.0514(19) 0.0056(13) 0.000 0.000
C9 0.0296(14) 0.0277(14) 0.0341(15) -0.0025(12) 0.000 0.000
N5 0.0259(11) 0.0242(11) 0.0253(12) 0.0006(9) 0.000 0.000
O3 0.0722(16) 0.0285(11) 0.0354(12) 0.0079(9) 0.000 0.000
Cl1 0.0437(4) 0.0537(5) 0.0226(4) -0.0006(3) 0.000 0.000
Cl10 0.0362(4) 0.0248(4) 0.0304(4) -0.0018(3) 0.000 0.000
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'
Cl Cl 0.1484 0.1585 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 C2 C4 123.5(3) . . ?
O3 C2 Cl1 122.1(2) . . ?
C4 C2 Cl1 114.4(2) . . ?
N5 C4 C9 120.1(3) . . ?
N5 C4 C2 113.9(2) . . ?
C9 C4 C2 125.9(3) . . ?
N5 C6 C7 120.6(3) . . ?
N5 C6 H6 119.7 . . ?
C7 C6 H6 119.7 . . ?
C8 C7 C6 118.6(3) . . ?
C8 C7 H7 120.7 . . ?
C6 C7 H7 120.7 . . ?
C7 C8 C9 120.4(3) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 H8 119.8 . . ?
C4 C9 C8 118.7(3) . . ?
C4 C9 H9 120.7 . . ?
C8 C9 H9 120.7 . . ?
C6 N5 C4 121.7(2) . . ?
C6 N5 H5 119.2 . . ?
C4 N5 H5 119.2 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C2 O3 1.183(4) . ?
C2 C4 1.495(4) . ?
C2 Cl1 1.752(3) . ?
C4 N5 1.352(4) . ?
C4 C9 1.371(4) . ?
C6 N5 1.330(4) . ?
C6 C7 1.381(4) . ?
C6 H6 1.0800 . ?
C7 C8 1.373(5) . ?
C7 H7 1.0800 . ?
C8 C9 1.391(4) . ?
C8 H8 1.0800 . ?
C9 H9 1.0800 . ?
N5 H5 1.0000 . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O3 C2 C4 N5 0.000(1) . . . . ?
Cl1 C2 C4 N5 180.0 . . . . ?
O3 C2 C4 C9 180.0 . . . . ?
Cl1 C2 C4 C9 0.0 . . . . ?
N5 C6 C7 C8 0.000(1) . . . . ?
C6 C7 C8 C9 0.0 . . . . ?
N5 C4 C9 C8 0.0 . . . . ?
C2 C4 C9 C8 180.0 . . . . ?
C7 C8 C9 C4 0.0 . . . . ?
C7 C6 N5 C4 0.000(1) . . . . ?
C9 C4 N5 C6 0.0 . . . . ?
C2 C4 N5 C6 180.0 . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139195498
