#------------------------------------------------------------------------------
#$Date: 2025-08-22 14:50:14 +0200 (Fri, 22 Aug 2025) $
#$Revision: 301863 $
#$URL: svn://saulius.grazulis.lt/cod-secondary/cif/7/20/47/7204731.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_7204731
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            '4-Chlorocarboxypyridinium Chloride'
_chemical_name_systematic        '4-Chlorocarboxypyridinium Chloride'
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.000
_cell_angle_beta                 97.060(1)
_cell_angle_gamma                90.000
_cell_formula_units_Z            4
_cell_length_a                   7.223(3)
_cell_length_b                   4.962(2)
_cell_length_c                   20.324(9)
_cell_measurement_reflns_used    1417
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      7
_cell_volume                     722.9(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 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'Rotation in phi and omega, 1 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  0.0173
_diffrn_reflns_av_sigmaI/netI    0.0329
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            2357
_diffrn_reflns_theta_full        25.69
_diffrn_reflns_theta_max         25.69
_diffrn_reflns_theta_min         3.13
_exptl_absorpt_coefficient_mu    0.819
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.636
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prisms
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.216
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     91
_refine_ls_number_reflns         1346
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0342
_refine_ls_R_factor_gt           0.0283
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0243P)^2^+0.5719P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0696
_refine_ls_wR_factor_ref         0.0730
_reflns_number_gt                1191
_reflns_number_total             1346
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b307875b.txt
_cod_data_source_block           1c
_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:

'_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 
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               7204731
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -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
Cl10 Cl -0.23062(6) 0.42406(9) 0.44963(2) 0.02554(16) Uani 1 1 d . . .
Cl1 Cl 0.60574(7) -0.26192(12) 0.28156(3) 0.03584(18) Uani 1 1 d . . .
O3 O 0.3452(2) -0.6098(3) 0.29288(7) 0.0331(4) Uani 1 1 d . . .
N7 N 0.1456(2) 0.1225(3) 0.43500(8) 0.0252(4) Uani 1 1 d . . .
H7 H 0.0805 0.2541 0.4615 0.030 Uiso 1 1 calc R . .
C2 C 0.4058(3) -0.3977(4) 0.31187(9) 0.0236(4) Uani 1 1 d . . .
C6 C 0.3314(3) 0.1358(4) 0.43804(10) 0.0252(4) Uani 1 1 d . . .
H6 H 0.4090 0.2783 0.4709 0.030 Uiso 1 1 calc R . .
C9 C 0.1283(3) -0.2364(4) 0.35932(10) 0.0248(4) Uani 1 1 d . . .
H9 H 0.0478 -0.3873 0.3301 0.030 Uiso 1 1 calc R . .
C4 C 0.3205(3) -0.2174(4) 0.35849(9) 0.0186(4) Uani 1 1 d . . .
C8 C 0.0433(3) -0.0588(4) 0.39811(10) 0.0278(5) Uani 1 1 d . . .
H8 H -0.1060 -0.0661 0.3987 0.033 Uiso 1 1 calc R . .
C5 C 0.4236(3) -0.0332(4) 0.39910(9) 0.0223(4) Uani 1 1 d . . .
H5 H 0.5733 -0.0222 0.4002 0.027 Uiso 1 1 calc R . .
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
Cl10 0.0210(3) 0.0251(3) 0.0308(3) -0.0068(2) 0.00453(19) -0.00097(18)
Cl1 0.0296(3) 0.0477(3) 0.0328(3) -0.0004(2) 0.0141(2) 0.0060(2)
O3 0.0512(10) 0.0223(8) 0.0253(8) -0.0039(6) 0.0026(7) 0.0025(7)
N7 0.0320(9) 0.0218(8) 0.0237(8) 0.0033(7) 0.0118(7) 0.0060(7)
C2 0.0289(10) 0.0240(11) 0.0177(9) 0.0028(8) 0.0026(8) 0.0048(8)
C6 0.0324(11) 0.0221(10) 0.0211(10) -0.0009(8) 0.0038(8) -0.0008(8)
C9 0.0226(10) 0.0272(10) 0.0242(10) 0.0007(8) 0.0020(8) -0.0036(8)
C4 0.0221(9) 0.0168(9) 0.0172(9) 0.0031(7) 0.0031(7) 0.0011(7)
C8 0.0226(10) 0.0318(11) 0.0302(11) 0.0046(9) 0.0075(8) 0.0002(9)
C5 0.0214(9) 0.0237(10) 0.0218(10) -0.0002(8) 0.0024(7) -0.0009(8)
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
C8 N7 C6 122.87(17) . . ?
C8 N7 H7 118.6 . . ?
C6 N7 H7 118.6 . . ?
O3 C2 C4 125.08(19) . . ?
O3 C2 Cl1 120.54(16) . . ?
C4 C2 Cl1 114.30(14) . . ?
N7 C6 C5 119.71(18) . . ?
N7 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
C8 C9 C4 118.62(18) . . ?
C8 C9 H9 120.7 . . ?
C4 C9 H9 120.7 . . ?
C5 C4 C9 120.05(17) . . ?
C5 C4 C2 122.71(17) . . ?
C9 C4 C2 117.22(17) . . ?
N7 C8 C9 119.86(18) . . ?
N7 C8 H8 120.1 . . ?
C9 C8 H8 120.1 . . ?
C6 C5 C4 118.73(18) . . ?
C6 C5 H5 120.6 . . ?
C4 C5 H5 120.6 . . ?
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
Cl1 C2 1.772(2) . ?
O3 C2 1.186(2) . ?
N7 C8 1.335(3) . ?
N7 C6 1.338(3) . ?
N7 H7 1.0000 . ?
C2 C4 1.490(3) . ?
C6 C5 1.379(3) . ?
C6 H6 1.0800 . ?
C9 C8 1.376(3) . ?
C9 C4 1.393(3) . ?
C9 H9 1.0800 . ?
C4 C5 1.386(3) . ?
C8 H8 1.0800 . ?
C5 H5 1.0800 . ?
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
C8 N7 C6 C5 3.6(3) . . . . ?
C8 C9 C4 C5 3.7(3) . . . . ?
C8 C9 C4 C2 -175.16(18) . . . . ?
O3 C2 C4 C5 153.91(19) . . . . ?
Cl1 C2 C4 C5 -29.5(2) . . . . ?
O3 C2 C4 C9 -27.2(3) . . . . ?
Cl1 C2 C4 C9 149.40(15) . . . . ?
C6 N7 C8 C9 -2.2(3) . . . . ?
C4 C9 C8 N7 -1.5(3) . . . . ?
N7 C6 C5 C4 -1.3(3) . . . . ?
C9 C4 C5 C6 -2.4(3) . . . . ?
C2 C4 C5 C6 176.46(17) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 10625973
2 PubChem 71676494
