#------------------------------------------------------------------------------
#$Date: 2021-04-06 04:16:15 +0300 (Tue, 06 Apr 2021) $
#$Revision: 263878 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/23/2022325.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_2022325
loop_
_publ_author_name
'Medviediev, Volodymyr'
'Daszkiewicz, Marek'
_publ_section_title
;
 Structural and theoretical analysis of 2-chloro-4-nitroaniline and
 2-methyl-6-nitroaniline salts
;
_journal_coeditor_code           DV3005
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              125
_journal_page_last               136
_journal_paper_doi               10.1107/S2053229621001455
_journal_volume                  77
_journal_year                    2021
_chemical_formula_iupac          'C6 H6 Cl N2 O2 +, Br -'
_chemical_formula_moiety         'C6 H6 Cl N2 O2 +, Br -'
_chemical_formula_sum            'C6 H6 Br Cl N2 O2'
_chemical_formula_weight         253.49
_chemical_name_systematic
;
2-Chloro-4-nitroanilinium bromide
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_method
;
Olex2 1.3
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.72152(9)
_cell_length_b                   7.90017(17)
_cell_length_c                   20.2729(4)
_cell_measurement_reflns_used    7548
_cell_measurement_temperature    295.0(10)
_cell_measurement_theta_max      27.3650
_cell_measurement_theta_min      2.7740
_cell_volume                     916.35(3)
_computing_cell_refinement
;
CrysAlis PRO (Rigaku OD, 2015)
;
_computing_data_collection
;
CrysAlis PRO (Rigaku OD, 2015)
;
_computing_data_reduction
;
CrysAlis PRO (Rigaku OD, 2015)
;
_computing_molecular_graphics
;
DIAMOND (Brandenburg & Putz, 2008) and OLEX2 (Dolomanov et al.,
2009)
;
_computing_publication_material
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_structure_refinement
;
SHELXL2018 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      295.0(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.6249
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku Xcalibur Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0347
_diffrn_reflns_av_unetI/netI     0.0229
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            18773
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.994
_diffrn_reflns_theta_min         2.767
_diffrn_source                   'fine-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    4.738
_exptl_absorpt_correction_T_max  0.446
_exptl_absorpt_correction_T_min  0.300
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
{CrysAlis PRO (Rigaku OD, 2015), based on expressions derived by
Clark & Reid (1995)]
;
_exptl_crystal_colour            'clear yellowish colourless'
_exptl_crystal_density_diffrn    1.837
_exptl_crystal_description       block
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.358
_exptl_crystal_size_mid          0.261
_exptl_crystal_size_min          0.216
_refine_diff_density_max         0.331
_refine_diff_density_min         -0.697
_refine_ls_abs_structure_details
;
Flack x determined using 881 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons et al.,  2013)
;
_refine_ls_abs_structure_Flack   -0.008(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.127
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     113
_refine_ls_number_reflns         2669
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.127
_refine_ls_R_factor_all          0.0366
_refine_ls_R_factor_gt           0.0278
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0322P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0598
_refine_ls_wR_factor_ref         0.0623
_reflns_number_gt                2340
_reflns_number_total             2669
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            dv3005sup1.cif
_cod_data_source_block           1
_cod_depositor_comments
'Adding full bibliography for 2022325--2022329.cif.'
_cod_database_code               2022325
_cod_database_fobs_code          2022325
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
loop_
_atom_site_type_symbol
_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_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br1 0.52443(5) 0.84406(4) 0.58461(2) 0.04093(10) Uani d 1 . .
Cl Cl1 -0.31036(14) 0.35586(13) 0.53964(4) 0.0489(2) Uani d 1 . .
O O1 0.0516(5) -0.1126(3) 0.68972(13) 0.0555(7) Uani d 1 . .
O O2 0.2906(5) 0.0104(4) 0.75612(13) 0.0684(8) Uani d 1 . .
N N1 0.0211(4) 0.6339(3) 0.57628(13) 0.0376(6) Uani d 1 . .
H H1A 0.139212 0.703405 0.585339 0.051(11) Uiso calc 1 . .
H H1B -0.112446 0.680764 0.589483 0.061(12) Uiso calc 1 . .
H H1C 0.015304 0.615323 0.533010 0.058(12) Uiso calc 1 . .
N N2 0.1576(5) 0.0117(4) 0.70883(14) 0.0435(7) Uani d 1 . .
C C1 0.0557(5) 0.4735(4) 0.61076(14) 0.0315(6) Uani d 1 . .
C C2 -0.0893(5) 0.3361(4) 0.59723(13) 0.0316(6) Uani d 1 . .
C C3 -0.0560(5) 0.1838(4) 0.62907(14) 0.0353(6) Uani d 1 . .
H H3 -0.150708 0.090853 0.620220 0.042 Uiso calc 1 . .
C C4 0.1227(5) 0.1743(4) 0.67451(14) 0.0336(6) Uani d 1 . .
C C5 0.2665(6) 0.3069(5) 0.68918(16) 0.0411(8) Uani d 1 . .
H H5 0.385125 0.295483 0.720224 0.049 Uiso calc 1 . .
C C6 0.2312(6) 0.4597(4) 0.65653(15) 0.0384(7) Uani d 1 . .
H H6 0.326256 0.552208 0.665712 0.046 Uiso calc 1 . .
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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -4 5 0.1164
0 4 -5 0.1000
-5 0 3 0.1783
5 0 -3 0.1651
0 1 5 0.1121
0 -1 -5 0.1491
-4 1 5 0.1579
-4 -1 -5 0.1878
3 1 5 0.1447
1 -1 -5 0.1600
-1 -1 5 0.1364
1 -1 5 0.1426
0 -1 -1 0.1382
2 -4 -5 0.1656
0 -1 5 0.1218
0 5 -2 0.1016
4 5 -5 0.1392
0 2 -5 0.0939
0 0 1 0.1054
0 4 -27 0.1226
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
H1A N1 H1B . . 109.5 ?
H1A N1 H1C . . 109.5 ?
H1B N1 H1C . . 109.5 ?
C1 N1 H1A . . 109.5 ?
C1 N1 H1B . . 109.5 ?
C1 N1 H1C . . 109.5 ?
O1 N2 O2 . . 123.5(3) ?
O1 N2 C4 . . 119.0(3) ?
O2 N2 C4 . . 117.5(3) ?
C2 C1 N1 . . 120.1(3) ?
C6 C1 N1 . . 119.5(3) ?
C6 C1 C2 . . 120.5(3) ?
C1 C2 Cl1 . . 119.9(2) ?
C3 C2 Cl1 . . 119.7(2) ?
C3 C2 C1 . . 120.4(3) ?
C2 C3 H3 . . 121.2 ?
C4 C3 C2 . . 117.6(3) ?
C4 C3 H3 . . 121.2 ?
C3 C4 N2 . . 117.6(3) ?
C5 C4 N2 . . 119.0(3) ?
C5 C4 C3 . . 123.4(3) ?
C4 C5 H5 . . 120.8 ?
C4 C5 C6 . . 118.3(3) ?
C6 C5 H5 . . 120.8 ?
C1 C6 C5 . . 119.8(3) ?
C1 C6 H6 . . 120.1 ?
C5 C6 H6 . . 120.1 ?
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
Cl1 C2 . 1.729(3) ?
O1 N2 . 1.217(4) ?
O2 N2 . 1.224(4) ?
N1 H1A . 0.8900 ?
N1 H1B . 0.8900 ?
N1 H1C . 0.8900 ?
N1 C1 . 1.461(4) ?
N2 C4 . 1.475(4) ?
C1 C2 . 1.393(4) ?
C1 C6 . 1.371(4) ?
C2 C3 . 1.379(4) ?
C3 H3 . 0.9300 ?
C3 C4 . 1.378(4) ?
C4 C5 . 1.365(5) ?
C5 H5 . 0.9300 ?
C5 C6 . 1.391(5) ?
C6 H6 . 0.9300 ?
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 H1A Br1 . 0.89 2.47 3.329(2) 162.7 yes
N1 H1B Br1 1_455 0.89 2.45 3.295(2) 159.3 yes
N1 H1C Br1 3_466 0.89 2.41 3.266(3) 162.5 yes
C3 H3 Br1 1_445 0.93 2.79 3.712(3) 172.0 yes
C5 H5 O2 4_656 0.93 2.56 3.199(4) 126.2 yes
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
Cl1 C2 C3 C4 . . . . 179.9(2) ?
O1 N2 C4 C3 . . . . 10.1(5) ?
O1 N2 C4 C5 . . . . -170.2(3) ?
O2 N2 C4 C3 . . . . -168.8(3) ?
O2 N2 C4 C5 . . . . 10.9(5) ?
N1 C1 C2 Cl1 . . . . -0.1(4) ?
N1 C1 C2 C3 . . . . 179.3(3) ?
N1 C1 C6 C5 . . . . -179.5(3) ?
N2 C4 C5 C6 . . . . -179.8(3) ?
C1 C2 C3 C4 . . . . 0.6(4) ?
C2 C1 C6 C5 . . . . 0.7(5) ?
C2 C3 C4 N2 . . . . 179.7(3) ?
C2 C3 C4 C5 . . . . -0.1(5) ?
C3 C4 C5 C6 . . . . -0.1(5) ?
C4 C5 C6 C1 . . . . -0.2(5) ?
C6 C1 C2 Cl1 . . . . 179.7(2) ?
C6 C1 C2 C3 . . . . -0.9(4) ?
