#------------------------------------------------------------------------------
#$Date: 2018-10-25 05:49:15 +0300 (Thu, 25 Oct 2018) $
#$Revision: 211630 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/13/2021317.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_2021317
loop_
_publ_author_name
'Marek, Paulina H.'
'Urban, Mateusz'
'Madura, Izabela D.'
_publ_section_title
;
 The study of interactions with a halogen atom: influence of NH₂ group
 insertion on the crystal structures of meta-bromonitrobenzene
 derivatives
;
_journal_coeditor_code           YP3165
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2053229618013608
_journal_volume                  74
_journal_year                    2018
_chemical_formula_iupac          'C6 H5 Br N2 O2'
_chemical_formula_moiety         'C6 H5 Br N2 O2'
_chemical_formula_sum            'C6 H5 Br N2 O2'
_chemical_formula_weight         217.03
_chemical_name_common            2-bromo-6-nitroaniline
_chemical_name_systematic        2-Bromo-6-nitroaniline
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 94.635(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.4477(2)
_cell_length_b                   11.4469(4)
_cell_length_c                   13.8244(5)
_cell_measurement_reflns_used    5872
_cell_measurement_temperature    130.0
_cell_measurement_theta_max      30.380
_cell_measurement_theta_min      2.313
_cell_volume                     701.53(5)
_computing_cell_refinement
;
SAINT (Bruker, 2016)
;
_computing_data_collection
;
APEX3 (Bruker, 2016)
;
_computing_data_reduction
;
SAINT (Bruker, 2016)
;
_computing_molecular_graphics
;
Mercury CSD (Macrae et al., 2008) and
ORTEP-3 for Windows (Farrugia, 2012)
;
_computing_publication_material
;
OLEX2 (Dolomanov et al.,  2009) and publCIF (Westrip,
2010)
;
_computing_structure_refinement
;
SHELXL (Sheldrick, 2015a)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015b)
;
_diffrn_ambient_temperature      130.0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker D8 Venture Photon II '
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           Mo-K\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0347
_diffrn_reflns_av_unetI/netI     0.0250
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            14025
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.575
_diffrn_reflns_theta_min         2.313
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    5.802
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.5224
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause et al., 2015)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    2.055
_exptl_crystal_description       needle
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.535
_refine_diff_density_min         -0.460
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     108
_refine_ls_number_reflns         2162
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0335
_refine_ls_R_factor_gt           0.0230
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0164P)²+0.5734P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0464
_refine_ls_wR_factor_ref         0.0504
_reflns_number_gt                1813
_reflns_number_total             2162
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            yp3165sup1.cif
_cod_data_source_block           2
_cod_database_code               2021317
_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.
;
_shelx_estimated_absorpt_t_min   0.194
_shelx_estimated_absorpt_t_max   0.325
loop_
_space_group_symop_operation_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_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
Br Br1 0.23474(4) 0.47820(2) 0.10999(2) 0.02263(6) Uani d 1
O O1 0.2381(3) 0.58496(13) 0.49773(10) 0.0274(3) Uani d 1
O O2 0.5543(3) 0.72679(14) 0.52156(10) 0.0321(3) Uani d 1
N N1 0.1533(3) 0.48393(15) 0.32640(11) 0.0198(3) Uani d 1
H H1A 0.109(6) 0.481(2) 0.3871(7) 0.034(7) Uiso d 1
H H1B 0.070(5) 0.4381(16) 0.2809(12) 0.027(6) Uiso d 1
N N2 0.4252(3) 0.65371(14) 0.46827(11) 0.0196(3) Uani d 1
C C1 0.3467(4) 0.56763(15) 0.30262(12) 0.0150(3) Uani d 1
C C2 0.4908(4) 0.64946(15) 0.36741(12) 0.0161(3) Uani d 1
C C3 0.6962(4) 0.73235(16) 0.33831(14) 0.0195(4) Uani d 1
H H3 0.7920 0.7841 0.3849 0.023 Uiso calc 1
C C4 0.7603(4) 0.73946(16) 0.24314(14) 0.0208(4) Uani d 1
H H4 0.8998 0.7958 0.2234 0.025 Uiso calc 1
C C5 0.6172(4) 0.66259(16) 0.17556(13) 0.0198(4) Uani d 1
H H5 0.6557 0.6678 0.1091 0.024 Uiso calc 1
C C6 0.4222(4) 0.57999(15) 0.20480(12) 0.0164(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 0.0000 0.0000 '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'
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
H1A N1 H1B 123(2)
C1 N1 H1A 117.3(16)
C1 N1 H1B 119.4(15)
O1 N2 C2 119.23(15)
O2 N2 O1 122.05(16)
O2 N2 C2 118.71(15)
N1 C1 C2 125.66(16)
N1 C1 C6 120.41(16)
C2 C1 C6 113.93(15)
C1 C2 N2 121.08(15)
C3 C2 N2 116.17(16)
C3 C2 C1 122.73(16)
C2 C3 H3 119.8
C4 C3 C2 120.50(17)
C4 C3 H3 119.8
C3 C4 H4 120.5
C3 C4 C5 119.02(17)
C5 C4 H4 120.5
C4 C5 H5 119.9
C6 C5 C4 120.22(17)
C6 C5 H5 119.9
C1 C6 Br1 118.06(13)
C5 C6 Br1 118.36(13)
C5 C6 C1 123.56(16)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C6 1.8958(17)
O1 N2 1.238(2)
O2 N2 1.226(2)
N1 H1A 0.878(5)
N1 H1B 0.878(5)
N1 C1 1.346(2)
N2 C2 1.448(2)
C1 C2 1.413(2)
C1 C6 1.426(2)
C2 C3 1.399(2)
C3 H3 0.9500
C3 C4 1.371(3)
C4 H4 0.9500
C4 C5 1.399(3)
C5 H5 0.9500
C5 C6 1.366(2)
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 O1 . 0.878(12) 1.986(17) 2.635(2) 130(2) yes
N1 H1A O1 3_566 0.878(12) 2.43(2) 3.201(2) 148(2) yes
N1 H1B Br1 . 0.878(18) 2.571(17) 3.0432(15) 114.6(15) yes
C3 H3 O2 . 0.95 2.33 2.661(2) 100 yes
C5 H5 O2 4_675 0.95 2.53 3.253(2) 133 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
O1 N2 C2 C1 -0.6(2)
O1 N2 C2 C3 177.77(16)
O2 N2 C2 C1 -179.49(16)
O2 N2 C2 C3 -1.2(2)
N1 C1 C2 N2 -3.6(3)
N1 C1 C2 C3 178.20(16)
N1 C1 C6 Br1 1.6(2)
N1 C1 C6 C5 -179.78(16)
N2 C2 C3 C4 -176.44(16)
C1 C2 C3 C4 1.9(3)
C2 C1 C6 Br1 -178.24(12)
C2 C1 C6 C5 0.4(2)
C2 C3 C4 C5 0.0(3)
C3 C4 C5 C6 -1.6(3)
C4 C5 C6 Br1 179.99(13)
C4 C5 C6 C1 1.4(3)
C6 C1 C2 N2 176.23(15)
C6 C1 C2 C3 -2.0(2)

_cod_database_fobs_code 2021317
