#------------------------------------------------------------------------------
#$Date: 2020-05-30 08:03:50 +0300 (Sat, 30 May 2020) $
#$Revision: 252480 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/34/2243410.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_2243410
loop_
_publ_author_name
'Anbarasan, Radhakrishnan'
'Eniya, Palaniyasan'
'Kalyana Sundar, Jeyaperumal'
'Mengesha Woldemariam, Menberu'
_publ_section_title
;
 Crystal structure and Hirshfeld surface analysis of 4-bromoanilinium
 nitrate
;
_journal_coeditor_code           MW2155
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              973
_journal_page_last               976
_journal_paper_doi               10.1107/S2056989020006945
_journal_volume                  76
_journal_year                    2020
_chemical_formula_iupac          'C6 H7 Br N +, N O3 -'
_chemical_formula_moiety         'C6 H7 Br N +, N O3 -'
_chemical_formula_sum            'C6 H7 Br N2 O3'
_chemical_formula_weight         235.0369
_chemical_name_common            '4-Bromoanilinium nitrate'
_chemical_name_systematic        'p-Bromoanilinium nitrate'
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 97.052(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.7123(8)
_cell_length_b                   23.4964(19)
_cell_length_c                   7.6264(6)
_cell_measurement_reflns_used    4609
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.11
_cell_measurement_theta_min      2.6
_cell_volume                     1727.2(2)
_computing_cell_refinement
;
SAINT (Bruker, 2004)
;
_computing_data_collection
;
APEX2 (Bruker, 2004)
;
_computing_data_reduction
;
SAINT (Bruker, 2004)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012)
;
_computing_publication_material
;
WinGX (Farrugia, 2012), PLATON (Spek, 2020), Mercury (Macrae
et al., 2020) and publCIF
(Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2017 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker SMART APEXII  CCD'
_diffrn_measurement_method       'ω and φ scan'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0584
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            16821
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.108
_diffrn_reflns_theta_min         2.113
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    4.73
_exptl_absorpt_correction_T_max  0.567
_exptl_absorpt_correction_T_min  0.374
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Sheldrick, 1996)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.808
_exptl_crystal_description       needle
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.676
_refine_diff_density_min         -0.84
_refine_ls_extinction_coef       0.0181(17)
_refine_ls_extinction_method
;
SHELXL2018/3 (Sheldrick 2015b)
;
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         4609
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.1304
_refine_ls_R_factor_gt           0.0593
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0927P)²+0.2455P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1828
_reflns_number_gt                2355
_reflns_number_total             4609
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            mw2155sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_original_formula_sum        'C6 H7 Br1 N2 O3'
_cod_database_code               2243410
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,y+1/2,-z+1/2
-x,-y,-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
N N1 1.0463(4) 0.32338(12) 0.2075(4) 0.0513(8) Uani d 1 . .
H H10 1.083534 0.351431 0.150589 0.077 Uiso calc 1 . .
H H9 1.063697 0.329131 0.323465 0.077 Uiso calc 1 . .
H H11 1.082988 0.290327 0.180092 0.077 Uiso calc 1 . .
N N2 0.8383(4) 0.52952(13) 0.2737(5) 0.0571(9) Uani d 1 . .
H H14 0.798745 0.556374 0.202137 0.086 Uiso calc 1 . .
H H13 0.880154 0.545557 0.371772 0.086 Uiso calc 1 . .
H H12 0.900523 0.510739 0.219564 0.086 Uiso calc 1 . .
N N3 0.0880(3) 0.32409(14) 0.6621(5) 0.0481(8) Uani d 1 . .
N N4 0.1286(3) 0.46630(13) 0.1594(5) 0.0531(9) Uani d 1 . .
O O2 0.1085(4) 0.28155(12) 0.5705(5) 0.0762(10) Uani d 1 . .
O O3 0.0604(4) 0.36877(12) 0.5772(5) 0.0891(12) Uani d 1 . .
O O4 0.1736(3) 0.42637(11) 0.0733(4) 0.0613(8) Uani d 1 . .
O O5 0.0995(5) 0.32142(18) 0.8212(5) 0.0941(12) Uani d 1 . .
O O6 0.0681(3) 0.45499(12) 0.2920(4) 0.0656(8) Uani d 1 . .
O O1 0.1429(4) 0.51579(11) 0.1125(5) 0.0766(10) Uani d 1 . .
C C1 0.6768(5) 0.28047(18) 0.1770(6) 0.0632(12) Uani d 1 . .
H H1 0.622297 0.253605 0.225586 0.076 Uiso calc 1 . .
C C2 0.6166(5) 0.31894(18) 0.0536(5) 0.0549(11) Uani d 1 . .
C C3 0.6968(5) 0.35869(17) -0.0173(6) 0.0611(12) Uani d 1 . .
H H2 0.655897 0.384689 -0.099684 0.073 Uiso calc 1 . .
C C4 0.8371(5) 0.36032(15) 0.0328(5) 0.0539(11) Uani d 1 . .
H H3 0.891543 0.387124 -0.016287 0.065 Uiso calc 1 . .
C C5 0.8970(4) 0.32216(14) 0.1558(5) 0.0449(9) Uani d 1 . .
C C6 0.8179(5) 0.28202(17) 0.2278(6) 0.0576(11) Uani d 1 . .
H H4 0.859217 0.256095 0.310167 0.069 Uiso calc 1 . .
C C7 0.7319(4) 0.48981(15) 0.3193(5) 0.0466(9) Uani d 1 . .
C C8 0.5964(5) 0.49725(19) 0.2493(6) 0.0638(12) Uani d 1 . .
H H5 0.571499 0.527478 0.173184 0.077 Uiso calc 1 . .
C C9 0.4971(5) 0.4596(2) 0.2925(7) 0.0779(14) Uani d 1 . .
H H6 0.40465 0.463954 0.245794 0.094 Uiso calc 1 . .
C C10 0.5363(5) 0.4159(2) 0.4046(6) 0.0640(12) Uani d 1 . .
C C11 0.6718(5) 0.40804(19) 0.4725(6) 0.0607(11) Uani d 1 . .
H H7 0.696645 0.377689 0.548105 0.073 Uiso calc 1 . .
C C12 0.7710(4) 0.44517(19) 0.4285(5) 0.0562(11) Uani d 1 . .
H H8 0.863752 0.439985 0.472598 0.067 Uiso calc 1 . .
Br Br1 0.42315(6) 0.31590(3) -0.02005(7) 0.0826(3) Uani d 1 . .
Br Br2 0.40126(7) 0.36433(3) 0.47100(8) 0.1017(3) Uani d 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 0 '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 0.006 '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_
_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
C5 N1 H10 . . 109.5 ?
C5 N1 H9 . . 109.5 ?
H10 N1 H9 . . 109.5 ?
C5 N1 H11 . . 109.5 ?
H10 N1 H11 . . 109.5 ?
H9 N1 H11 . . 109.5 ?
C7 N2 H14 . . 109.5 ?
C7 N2 H13 . . 109.5 ?
H14 N2 H13 . . 109.5 ?
C7 N2 H12 . . 109.5 ?
H14 N2 H12 . . 109.5 ?
H13 N2 H12 . . 109.5 ?
O5 N3 O3 . . 123.7(4) ?
O5 N3 O2 . . 121.3(4) ?
O3 N3 O2 . . 115.0(4) ?
O1 N4 O4 . . 119.8(4) ?
O1 N4 O6 . . 120.9(4) ?
O4 N4 O6 . . 119.3(3) ?
C6 C1 C2 . . 119.8(4) ?
C6 C1 H1 . . 120.1 ?
C2 C1 H1 . . 120.1 ?
C3 C2 C1 . . 120.1(5) ?
C3 C2 Br1 . . 120.0(3) ?
C1 C2 Br1 . . 119.9(4) ?
C2 C3 C4 . . 120.3(4) ?
C2 C3 H2 . . 119.9 ?
C4 C3 H2 . . 119.9 ?
C3 C4 C5 . . 119.7(4) ?
C3 C4 H3 . . 120.2 ?
C5 C4 H3 . . 120.2 ?
C6 C5 C4 . . 120.7(4) ?
C6 C5 N1 . . 119.5(3) ?
C4 C5 N1 . . 119.8(4) ?
C5 C6 C1 . . 119.4(4) ?
C5 C6 H4 . . 120.3 ?
C1 C6 H4 . . 120.3 ?
C12 C7 C8 . . 121.2(4) ?
C12 C7 N2 . . 118.9(4) ?
C8 C7 N2 . . 119.9(4) ?
C7 C8 C9 . . 119.5(4) ?
C7 C8 H5 . . 120.3 ?
C9 C8 H5 . . 120.3 ?
C10 C9 C8 . . 119.0(4) ?
C10 C9 H6 . . 120.5 ?
C8 C9 H6 . . 120.5 ?
C9 C10 C11 . . 121.5(4) ?
C9 C10 Br2 . . 120.0(4) ?
C11 C10 Br2 . . 118.5(4) ?
C10 C11 C12 . . 119.6(4) ?
C10 C11 H7 . . 120.2 ?
C12 C11 H7 . . 120.2 ?
C7 C12 C11 . . 119.2(4) ?
C7 C12 H8 . . 120.4 ?
C11 C12 H8 . . 120.4 ?
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
N1 C5 . 1.456(5) ?
N1 H10 . 0.89 ?
N1 H9 . 0.89 ?
N1 H11 . 0.89 ?
N2 C7 . 1.465(5) ?
N2 H14 . 0.89 ?
N2 H13 . 0.89 ?
N2 H12 . 0.89 ?
N3 O5 . 1.207(5) ?
N3 O3 . 1.245(4) ?
N3 O2 . 1.249(4) ?
N4 O1 . 1.229(4) ?
N4 O4 . 1.254(4) ?
N4 O6 . 1.258(4) ?
C1 C6 . 1.378(7) ?
C1 C2 . 1.382(6) ?
C1 H1 . 0.93 ?
C2 C3 . 1.369(6) ?
C2 Br1 . 1.895(5) ?
C3 C4 . 1.369(6) ?
C3 H2 . 0.93 ?
C4 C5 . 1.375(5) ?
C4 H3 . 0.93 ?
C5 C6 . 1.373(6) ?
C6 H4 . 0.93 ?
C7 C12 . 1.364(6) ?
C7 C8 . 1.370(6) ?
C8 C9 . 1.379(7) ?
C8 H5 . 0.93 ?
C9 C10 . 1.360(7) ?
C9 H6 . 0.93 ?
C10 C11 . 1.366(6) ?
C10 Br2 . 1.900(4) ?
C11 C12 . 1.372(6) ?
C11 H7 . 0.93 ?
C12 H8 . 0.93 ?
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
N1 H9 O2 1_655 0.89 2.19 2.930(5) 140
N1 H9 O3 1_655 0.89 2.15 3.002(5) 160
N1 H10 O4 1_655 0.89 2.08 2.957(4) 167
N1 H11 O2 4_654 0.89 1.91 2.773(4) 162
N2 H12 O1 1_655 0.89 2.59 3.356(6) 145
N2 H12 O6 1_655 0.89 2.11 2.827(5) 137
N2 H12 O1 3_665 0.89 2.59 3.158(5) 122
N2 H13 O3 3_666 0.89 2.12 2.774(5) 130
N2 H13 O6 3_666 0.89 2.55 3.345(5) 149
N2 H14 O4 3_665 0.89 2.19 2.831(5) 129
C4 H3 O1 3_665 0.93 2.41 3.129(5) 134
C12 H8 O3 1_655 0.93 2.59 3.410(5) 147
C12 H8 O6 1_655 0.93 2.58 3.1943(3) 124
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
C6 C1 C2 C3 . . . . -0.4(7) ?
C6 C1 C2 Br1 . . . . 178.7(3) ?
C1 C2 C3 C4 . . . . 0.4(6) ?
Br1 C2 C3 C4 . . . . -178.7(3) ?
C2 C3 C4 C5 . . . . -0.6(6) ?
C3 C4 C5 C6 . . . . 0.7(6) ?
C3 C4 C5 N1 . . . . 179.2(3) ?
C4 C5 C6 C1 . . . . -0.6(6) ?
N1 C5 C6 C1 . . . . -179.2(4) ?
C2 C1 C6 C5 . . . . 0.4(7) ?
C12 C7 C8 C9 . . . . 1.2(7) ?
N2 C7 C8 C9 . . . . 179.8(4) ?
C7 C8 C9 C10 . . . . 0.2(7) ?
C8 C9 C10 C11 . . . . -1.1(8) ?
C8 C9 C10 Br2 . . . . 178.5(4) ?
C9 C10 C11 C12 . . . . 0.6(7) ?
Br2 C10 C11 C12 . . . . -179.1(3) ?
C8 C7 C12 C11 . . . . -1.8(6) ?
N2 C7 C12 C11 . . . . 179.6(4) ?
C10 C11 C12 C7 . . . . 0.9(6) ?
