#------------------------------------------------------------------------------
#$Date: 2018-10-25 05:49:15 +0300 (Thu, 25 Oct 2018) $
#$Revision: 211630 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/13/2021316.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_2021316
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_absolute_configuration ad
_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            4-bromo-2-nitroaniline
_chemical_name_systematic        4-Bromo-2-nitroaniline
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_Hall           'P -2yc'
_space_group_name_H-M_alt        'P 1 c 1'
_symmetry_space_group_name_Hall  'P -2yc'
_symmetry_space_group_name_H-M   'P 1 c 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                 98.662(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.1643(11)
_cell_length_b                   3.8275(4)
_cell_length_c                   17.2764(16)
_cell_measurement_reflns_used    3126
_cell_measurement_temperature    130.0
_cell_measurement_theta_max      27.63
_cell_measurement_theta_min      2.39
_cell_volume                     729.82(12)
_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           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0586
_diffrn_reflns_av_unetI/netI     0.0810
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            12367
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.490
_diffrn_reflns_theta_min         2.385
_diffrn_source
;
TRIUMPH monochromator and  fine focus
 sealed tube
;
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    5.577
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.5788
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause et al., 2015)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.975
_exptl_crystal_description       needle
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.38
_refine_diff_density_max         0.510
_refine_diff_density_min         -0.773
_refine_ls_abs_structure_details
;
Flack x determined using 1017 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons et al., 2013)
;
_refine_ls_abs_structure_Flack   0.030(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     215
_refine_ls_number_reflns         3712
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0620
_refine_ls_R_factor_gt           0.0410
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     'w=1/[σ²(Fo²)] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0738
_refine_ls_wR_factor_ref         0.0800
_reflns_number_gt                2965
_reflns_number_total             3712
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            yp3165sup1.cif
_cod_data_source_block           1
_cod_database_code               2021316
_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   0.135
_shelx_estimated_absorpt_t_max   0.214
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, 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 0.27039(4) 0.95174(18) 0.14819(3) 0.0270(2) Uani d 1
O O1 0.1481(4) 0.7273(14) 0.4930(3) 0.0280(12) Uani d 1
O O2 0.0525(4) 1.0151(13) 0.3946(3) 0.0312(12) Uani d 1
N N1 0.3685(7) 0.4902(15) 0.4868(4) 0.0277(16) Uani d 1
H H1A 0.313(5) 0.521(16) 0.518(3) 0.018(18) Uiso d 1
H H1B 0.440(3) 0.40(2) 0.504(5) 0.04(2) Uiso d 1
N N2 0.1407(5) 0.8386(15) 0.4244(3) 0.0208(12) Uani d 1
C C1 0.3445(6) 0.6017(18) 0.4122(4) 0.0196(14) Uani d 1
C C2 0.2357(6) 0.7667(18) 0.3791(4) 0.0165(13) Uani d 1
C C3 0.2143(6) 0.8733(15) 0.3005(3) 0.0143(12) Uani d 1
H H3 0.1404 0.9844 0.2797 0.017 Uiso calc 1
C C4 0.3009(6) 0.8151(17) 0.2546(4) 0.0192(14) Uani d 1
C C5 0.4104(6) 0.6541(18) 0.2851(4) 0.0210(15) Uani d 1
H H5 0.4699 0.6126 0.2523 0.025 Uiso calc 1
C C6 0.4319(6) 0.5560(18) 0.3623(4) 0.0250(15) Uani d 1
H H6 0.5079 0.4547 0.3826 0.030 Uiso calc 1
Br Br11 0.77175(6) 0.51283(17) 0.85196(4) 0.0268(2) Uani d 1
O O11 0.6691(5) 1.1576(16) 0.5080(3) 0.0378(14) Uani d 1
O O12 0.5605(4) 1.1624(16) 0.6013(3) 0.0387(14) Uani d 1
N N11 0.8927(6) 0.9025(18) 0.5326(4) 0.0291(14) Uani d 1
H H11A 0.969(2) 0.86(2) 0.528(5) 0.04(2) Uiso d 1
H H11B 0.837(5) 1.016(18) 0.501(4) 0.04(3) Uiso d 1
N N12 0.6553(5) 1.0795(16) 0.5758(4) 0.0254(14) Uani d 1
C C11 0.8602(6) 0.8231(17) 0.6033(4) 0.0187(14) Uani d 1
C C12 0.7478(6) 0.9009(16) 0.6259(4) 0.0172(13) Uani d 1
C C13 0.7217(6) 0.8121(17) 0.7007(4) 0.0179(14) Uani d 1
H H13 0.6451 0.8691 0.7149 0.022 Uiso calc 1
C C14 0.8055(6) 0.6462(16) 0.7522(4) 0.0159(13) Uani d 1
C C15 0.9211(6) 0.5656(16) 0.7317(4) 0.0196(13) Uani d 1
H H15 0.9808 0.4539 0.7684 0.024 Uiso calc 1
C C16 0.9454(6) 0.6492(17) 0.6595(4) 0.0199(14) Uani d 1
H H16 1.0223 0.5894 0.6460 0.024 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'
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 122(7)
C1 N1 H1A 119(5)
C1 N1 H1B 119(6)
O1 N2 C2 120.2(5)
O2 N2 O1 120.9(5)
O2 N2 C2 118.9(5)
N1 C1 C2 124.3(7)
N1 C1 C6 119.4(6)
C6 C1 C2 116.3(6)
C1 C2 N2 121.8(6)
C3 C2 N2 116.1(6)
C3 C2 C1 122.1(6)
C2 C3 H3 120.5
C4 C3 C2 119.1(6)
C4 C3 H3 120.5
C3 C4 Br1 118.8(5)
C3 C4 C5 120.7(6)
C5 C4 Br1 120.5(5)
C4 C5 H5 119.9
C6 C5 C4 120.2(6)
C6 C5 H5 119.9
C1 C6 H6 119.2
C5 C6 C1 121.7(6)
C5 C6 H6 119.2
H11A N11 H11B 130(8)
C11 N11 H11A 115(5)
C11 N11 H11B 115(6)
O11 N12 O12 120.3(6)
O11 N12 C12 120.6(6)
O12 N12 C12 119.0(6)
N11 C11 C12 125.1(6)
N11 C11 C16 118.5(6)
C12 C11 C16 116.4(6)
C11 C12 N12 122.1(6)
C11 C12 C13 121.5(6)
C13 C12 N12 116.4(5)
C12 C13 H13 120.0
C14 C13 C12 120.0(6)
C14 C13 H13 120.0
C13 C14 Br11 121.0(5)
C13 C14 C15 120.3(6)
C15 C14 Br11 118.8(5)
C14 C15 H15 120.2
C16 C15 C14 119.6(6)
C16 C15 H15 120.2
C11 C16 H16 118.9
C15 C16 C11 122.3(6)
C15 C16 H16 118.9
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C4 1.892(7)
O1 N2 1.249(6)
O2 N2 1.241(7)
N1 H1A 0.879(7)
N1 H1B 0.879(7)
N1 C1 1.346(10)
N2 C2 1.436(8)
C1 C2 1.411(9)
C1 C6 1.407(10)
C2 C3 1.405(8)
C3 H3 0.9500
C3 C4 1.358(8)
C4 C5 1.399(9)
C5 H5 0.9500
C5 C6 1.370(10)
C6 H6 0.9500
Br11 C14 1.890(6)
O11 N12 1.240(8)
O12 N12 1.247(7)
N11 H11A 0.881(7)
N11 H11B 0.880(7)
N11 C11 1.360(9)
N12 C12 1.419(9)
C11 C12 1.401(9)
C11 C16 1.419(9)
C12 C13 1.409(9)
C13 H13 0.9500
C13 C14 1.348(9)
C14 C15 1.421(9)
C15 H15 0.9500
C15 C16 1.355(9)
C16 H16 0.9500
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 . 0.89(6) 1.99(6) 2.640(9) 129(4) yes
N1 H1B O12 1_545 0.88(5) 2.19(7) 2.967(9) 148(6) yes
N11 H11A O1 1_655 0.88(3) 2.23(4) 3.104(8) 169(8) yes
N11 H11B O11 . 0.88(6) 1.97(6) 2.655(9) 134(6) yes
N11 H11B N12 . 0.88(6) 2.58(6) 2.939(9) 106(5) 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
Br1 C4 C5 C6 179.9(5)
O1 N2 C2 C1 -6.5(10)
O1 N2 C2 C3 174.2(6)
O2 N2 C2 C1 172.8(6)
O2 N2 C2 C3 -6.6(9)
N1 C1 C2 N2 1.7(11)
N1 C1 C2 C3 -179.0(6)
N1 C1 C6 C5 177.7(7)
N2 C2 C3 C4 179.5(6)
C1 C2 C3 C4 0.2(10)
C2 C1 C6 C5 -2.5(10)
C2 C3 C4 Br1 178.9(5)
C2 C3 C4 C5 -0.5(9)
C3 C4 C5 C6 -0.7(10)
C4 C5 C6 C1 2.2(10)
C6 C1 C2 N2 -178.0(6)
C6 C1 C2 C3 1.3(10)
Br11 C14 C15 C16 177.9(5)
O11 N12 C12 C11 3.7(10)
O11 N12 C12 C13 -177.7(6)
O12 N12 C12 C11 -175.1(6)
O12 N12 C12 C13 3.6(9)
N11 C11 C12 N12 -0.8(10)
N11 C11 C12 C13 -179.4(7)
N11 C11 C16 C15 178.9(7)
N12 C12 C13 C14 -179.1(6)
C11 C12 C13 C14 -0.5(10)
C12 C11 C16 C15 -0.8(10)
C12 C13 C14 Br11 -178.3(5)
C12 C13 C14 C15 1.1(10)
C13 C14 C15 C16 -1.6(10)
C14 C15 C16 C11 1.4(10)
C16 C11 C12 N12 178.9(6)
C16 C11 C12 C13 0.3(9)

_cod_database_fobs_code 2021316
