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#$Date: 2025-08-23 02:36:08 +0300 (Sat, 23 Aug 2025) $
#$Revision: 301880 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/27/8102754.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_8102754
loop_
_publ_author_name
'Hong Li'
'Li-Ming Qiang'
'Jun-Ling Si'
'Duo-Bin Mao'
_publ_section_title
;
 Crystal structure of N-(4-bromophenyl)-4-nitrobenzeneamine,
 C12H9BrN2O2
;
_journal_issue                   3
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              473
_journal_volume                  225
_journal_year                    2010
_chemical_formula_sum            'C12 H9 Br N2 O2'
_chemical_formula_weight         293.12
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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            8
_cell_length_a                   15.1396(18)
_cell_length_b                   6.7130(8)
_cell_length_c                   23.575(3)
_cell_measurement_reflns_used    2023
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      21.63
_cell_measurement_theta_min      3.20
_cell_volume                     2396.0(5)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0503
_diffrn_reflns_av_sigmaI/netI    0.0333
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            14440
_diffrn_reflns_theta_full        25.49
_diffrn_reflns_theta_max         25.49
_diffrn_reflns_theta_min         2.69
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.422
_exptl_absorpt_correction_T_max  0.6842
_exptl_absorpt_correction_T_min  0.3892
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.625
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1168
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.299
_refine_diff_density_min         -0.404
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.877
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2225
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.877
_refine_ls_R_factor_all          0.0818
_refine_ls_R_factor_gt           0.0367
_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/[σ²(Fo²)+(0.1000P)²+0.1015P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1077
_refine_ls_wR_factor_ref         0.1458
_reflns_number_gt                1308
_reflns_number_total             2225
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1267-3049.cff
_cod_data_source_block           c
_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 1555 2011-01-17 13:19:09Z saulius 
;
_cod_original_cell_volume        2395.9(5)
_cod_original_sg_symbol_H-M      Pbca
_cod_database_code               8102754
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'
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
N1 N 0.6870(2) 0.1389(5) 1.04318(17) 0.0579(8) Uani 1 1 d . . .
N2 N 0.4040(2) 0.3165(5) 0.89942(14) 0.0578(9) Uani 1 1 d . . .
H2N H 0.3601 0.3571 0.9179 0.087 Uiso 1 1 d R . .
O1 O 0.6780(2) 0.1626(5) 1.09421(15) 0.0774(9) Uani 1 1 d . . .
O2 O 0.75513(18) 0.0729(5) 1.02186(14) 0.0758(9) Uani 1 1 d . . .
Br1 Br 0.35237(4) 0.22016(9) 0.64573(2) 0.0851(3) Uani 1 1 d . . .
C1 C 0.4753(3) 0.2715(5) 0.93309(17) 0.0464(9) Uani 1 1 d . . .
C2 C 0.4639(3) 0.2719(5) 0.99249(17) 0.0484(9) Uani 1 1 d . . .
H2 H 0.4085 0.2997 1.0076 0.058 Uiso 1 1 calc R . .
C3 C 0.5327(3) 0.2321(5) 1.02827(17) 0.0476(9) Uani 1 1 d . . .
H3 H 0.5246 0.2347 1.0674 0.057 Uiso 1 1 calc R . .
C4 C 0.6144(2) 0.1881(5) 1.00549(17) 0.0466(10) Uani 1 1 d . . .
C5 C 0.6285(3) 0.1892(6) 0.94776(19) 0.0544(10) Uani 1 1 d . . .
H5 H 0.6842 0.1608 0.9332 0.065 Uiso 1 1 calc R . .
C6 C 0.5596(3) 0.2326(5) 0.91169(19) 0.0543(10) Uani 1 1 d . . .
H6 H 0.5693 0.2360 0.8727 0.065 Uiso 1 1 calc R . .
C7 C 0.3958(3) 0.2930(6) 0.84042(18) 0.0514(10) Uani 1 1 d . . .
C8 C 0.4318(3) 0.1335(6) 0.81150(18) 0.0593(11) Uani 1 1 d . . .
H8 H 0.4648 0.0390 0.8311 0.071 Uiso 1 1 calc R . .
C9 C 0.4194(3) 0.1133(7) 0.75403(17) 0.0614(11) Uani 1 1 d . . .
H9 H 0.4442 0.0057 0.7350 0.074 Uiso 1 1 calc R . .
C10 C 0.3710(3) 0.2503(6) 0.72495(19) 0.0551(11) Uani 1 1 d . . .
C11 C 0.3328(3) 0.4072(7) 0.75294(17) 0.0650(12) Uani 1 1 d . . .
H11 H 0.2982 0.4980 0.7332 0.078 Uiso 1 1 calc R . .
C12 C 0.3459(2) 0.4302(6) 0.81036(17) 0.0626(11) Uani 1 1 d . . .
H12 H 0.3210 0.5384 0.8291 0.075 Uiso 1 1 calc R . .
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'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 N1 O2 122.9(4) . . ?
O1 N1 C4 119.3(4) . . ?
O2 N1 C4 117.8(4) . . ?
C1 N2 C7 128.1(3) . . ?
C1 N2 H2N 113.1 . . ?
C7 N2 H2N 118.7 . . ?
N2 C1 C6 123.4(4) . . ?
N2 C1 C2 118.6(4) . . ?
C6 C1 C2 118.0(4) . . ?
C3 C2 C1 121.3(4) . . ?
C3 C2 H2 119.3 . . ?
C1 C2 H2 119.3 . . ?
C2 C3 C4 119.0(4) . . ?
C2 C3 H3 120.5 . . ?
C4 C3 H3 120.5 . . ?
C5 C4 C3 121.5(4) . . ?
C5 C4 N1 119.2(4) . . ?
C3 C4 N1 119.3(4) . . ?
C6 C5 C4 119.6(4) . . ?
C6 C5 H5 120.2 . . ?
C4 C5 H5 120.2 . . ?
C5 C6 C1 120.6(4) . . ?
C5 C6 H6 119.7 . . ?
C1 C6 H6 119.7 . . ?
C8 C7 C12 118.6(4) . . ?
C8 C7 N2 122.7(4) . . ?
C12 C7 N2 118.7(4) . . ?
C9 C8 C7 120.6(4) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
C10 C9 C8 120.2(4) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C9 C10 C11 120.2(4) . . ?
C9 C10 Br1 120.2(3) . . ?
C11 C10 Br1 119.5(3) . . ?
C10 C11 C12 120.0(4) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
C11 C12 C7 120.4(4) . . ?
C11 C12 H12 119.8 . . ?
C7 C12 H12 119.8 . . ?
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
N1 O1 1.221(4) . ?
N1 O2 1.230(4) . ?
N1 C4 1.452(5) . ?
N2 C1 1.373(5) . ?
N2 C7 1.405(5) . ?
N2 H2N 0.8405 . ?
Br1 C10 1.899(5) . ?
C1 C6 1.398(6) . ?
C1 C2 1.411(6) . ?
C2 C3 1.367(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.379(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.378(6) . ?
C5 C6 1.377(6) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.381(6) . ?
C7 C12 1.386(6) . ?
C8 C9 1.375(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.362(6) . ?
C9 H9 0.9300 . ?
C10 C11 1.370(6) . ?
C11 C12 1.377(6) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2N O2 0.84 2.18 3.012(4) 169.6 4_457
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
C7 N2 C1 C6 14.2(6) . . . . ?
C7 N2 C1 C2 -168.3(4) . . . . ?
N2 C1 C2 C3 -178.7(3) . . . . ?
C6 C1 C2 C3 -1.1(5) . . . . ?
C1 C2 C3 C4 -0.9(5) . . . . ?
C2 C3 C4 C5 1.9(5) . . . . ?
C2 C3 C4 N1 -177.9(3) . . . . ?
O1 N1 C4 C5 170.6(4) . . . . ?
O2 N1 C4 C5 -10.0(5) . . . . ?
O1 N1 C4 C3 -9.6(5) . . . . ?
O2 N1 C4 C3 169.8(3) . . . . ?
C3 C4 C5 C6 -0.8(6) . . . . ?
N1 C4 C5 C6 179.0(3) . . . . ?
C4 C5 C6 C1 -1.3(6) . . . . ?
N2 C1 C6 C5 179.7(3) . . . . ?
C2 C1 C6 C5 2.2(5) . . . . ?
C1 N2 C7 C8 36.9(6) . . . . ?
C1 N2 C7 C12 -146.3(4) . . . . ?
C12 C7 C8 C9 0.9(6) . . . . ?
N2 C7 C8 C9 177.7(4) . . . . ?
C7 C8 C9 C10 -0.3(7) . . . . ?
C8 C9 C10 C11 -1.3(6) . . . . ?
C8 C9 C10 Br1 -179.1(3) . . . . ?
C9 C10 C11 C12 2.1(6) . . . . ?
Br1 C10 C11 C12 179.9(3) . . . . ?
C10 C11 C12 C7 -1.5(6) . . . . ?
C8 C7 C12 C11 -0.1(6) . . . . ?
N2 C7 C12 C11 -177.0(4) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 3958655
2 PubChem 4771874
