#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/33/2233300.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_2233300
loop_
_publ_author_name
'Saeed, Sohail'
'Rashid, Naghmana'
'Hussain, Rizwan'
'Wong, Wing-Tak'
_publ_section_title
;
 N-(4-Bromophenyl)-3,5-dinitrobenzamide
;
_journal_coeditor_code           TK5029
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o26
_journal_paper_doi               10.1107/S1600536811051464
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C13 H8 Br N3 O5'
_chemical_formula_moiety         'C13 H8 Br N3 O5'
_chemical_formula_sum            'C13 H8 Br N3 O5'
_chemical_formula_weight         366.13
_chemical_name_systematic
;
N-(4-Bromophenyl)-3,5-dinitrobenzamide
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_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                 101.652(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.1273(2)
_cell_length_b                   26.6676(7)
_cell_length_c                   7.5428(2)
_cell_measurement_reflns_used    18250
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.03
_cell_measurement_theta_min      2.86
_cell_volume                     1404.10(7)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'ω and φ scan'
_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  0.0597
_diffrn_reflns_av_sigmaI/netI    0.0359
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            18250
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         2.86
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.956
_exptl_absorpt_correction_T_max  0.4709
_exptl_absorpt_correction_T_min  0.2883
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.732
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.253
_refine_diff_density_min         -0.456
_refine_ls_extinction_coef       0.0074(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     204
_refine_ls_number_reflns         2476
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.097
_refine_ls_R_factor_all          0.0491
_refine_ls_R_factor_gt           0.0345
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0472P)²+0.9282P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0914
_refine_ls_wR_factor_ref         0.1082
_reflns_number_gt                2007
_reflns_number_total             2476
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            tk5029.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2233300
_cod_database_fobs_code          2233300
loop_
_symmetry_equiv_pos_as_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_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
Br Br1 0.80856(6) 0.046874(16) 0.25109(7) 0.0884(2) Uani d . 1 1
O O1 0.6333(3) 0.28369(8) 0.5032(3) 0.0569(6) Uani d . 1 1
O O2 0.9867(5) 0.31665(12) 1.3107(3) 0.0879(9) Uani d . 1 1
O O3 0.9761(6) 0.39563(13) 1.3387(4) 0.1162(14) Uani d . 1 1
O O4 0.8205(5) 0.50043(9) 0.8040(5) 0.0986(10) Uani d . 1 1
O O5 0.7279(6) 0.46522(10) 0.5447(5) 0.0967(11) Uani d . 1 1
N N1 0.8777(3) 0.24105(8) 0.6787(3) 0.0395(6) Uani d . 1 1
N N2 0.9563(5) 0.35817(13) 1.2475(4) 0.0651(9) Uani d . 1 1
N N3 0.7853(5) 0.46389(11) 0.7070(6) 0.0655(9) Uani d . 1 1
C C1 0.7638(4) 0.28096(10) 0.6368(4) 0.0393(6) Uani d . 1 1
C C2 0.8027(3) 0.32503(10) 0.7622(4) 0.0341(6) Uani d . 1 1
C C3 0.8632(4) 0.32045(10) 0.9473(4) 0.0362(6) Uani d . 1 1
H H3 0.8834 0.2890 1.0013 0.043 Uiso calc R 1 1
C C4 0.8932(4) 0.36369(11) 1.0508(4) 0.0430(7) Uani d . 1 1
C C5 0.8704(4) 0.41094(11) 0.9800(4) 0.0487(8) Uani d . 1 1
H H5 0.8934 0.4394 1.0524 0.058 Uiso calc R 1 1
C C6 0.8110(4) 0.41394(10) 0.7935(5) 0.0456(7) Uani d . 1 1
C C7 0.7736(4) 0.37237(10) 0.6849(4) 0.0405(6) Uani d . 1 1
H H7 0.7293 0.3759 0.5608 0.049 Uiso calc R 1 1
C C8 0.8647(4) 0.19583(10) 0.5760(4) 0.0392(6) Uani d . 1 1
C C9 0.8261(4) 0.19669(12) 0.3885(4) 0.0488(7) Uani d . 1 1
H H9 0.8107 0.2271 0.3268 0.059 Uiso calc R 1 1
C C10 0.8108(5) 0.15204(15) 0.2943(5) 0.0580(9) Uani d . 1 1
H H10 0.7828 0.1522 0.1685 0.070 Uiso calc R 1 1
C C11 0.8370(4) 0.10718(13) 0.3874(5) 0.0576(9) Uani d . 1 1
C C12 0.8826(5) 0.10586(12) 0.5729(5) 0.0561(8) Uani d . 1 1
H H12 0.9045 0.0754 0.6338 0.067 Uiso calc R 1 1
C C13 0.8955(4) 0.15065(11) 0.6683(4) 0.0481(8) Uani d . 1 1
H H13 0.9247 0.1504 0.7942 0.058 Uiso calc R 1 1
H H1N 0.958(4) 0.2412(10) 0.792(4) 0.035(7) Uiso d . 1 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'
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
C1 N1 C8 125.1(2)
C1 N1 H1N 116.5(17)
C8 N1 H1N 117.7(17)
O3 N2 O2 123.0(3)
O3 N2 C4 118.1(3)
O2 N2 C4 119.0(3)
O5 N3 O4 124.9(3)
O5 N3 C6 117.3(3)
O4 N3 C6 117.7(4)
O1 C1 N1 124.4(3)
O1 C1 C2 118.9(2)
N1 C1 C2 116.7(2)
C3 C2 C7 119.6(2)
C3 C2 C1 123.3(2)
C7 C2 C1 117.1(2)
C2 C3 C4 118.5(2)
C2 C3 H3 120.7
C4 C3 H3 120.7
C5 C4 C3 123.7(3)
C5 C4 N2 118.4(3)
C3 C4 N2 117.8(3)
C4 C5 C6 116.0(3)
C4 C5 H5 122.0
C6 C5 H5 122.0
C7 C6 C5 122.8(3)
C7 C6 N3 118.2(3)
C5 C6 N3 119.0(3)
C6 C7 C2 119.3(3)
C6 C7 H7 120.3
C2 C7 H7 120.3
C9 C8 C13 120.4(3)
C9 C8 N1 121.2(3)
C13 C8 N1 118.4(3)
C10 C9 C8 119.4(3)
C10 C9 H9 120.3
C8 C9 H9 120.3
C9 C10 C11 119.8(3)
C9 C10 H10 120.1
C11 C10 H10 120.1
C12 C11 C10 121.4(3)
C12 C11 Br1 120.6(3)
C10 C11 Br1 118.0(3)
C11 C12 C13 118.9(3)
C11 C12 H12 120.5
C13 C12 H12 120.5
C8 C13 C12 120.0(3)
C8 C13 H13 120.0
C12 C13 H13 120.0
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C11 1.898(3)
O1 C1 1.228(3)
O2 N2 1.208(4)
O3 N2 1.205(4)
O4 N3 1.214(4)
O5 N3 1.211(5)
N1 C1 1.337(4)
N1 C8 1.426(3)
N1 H1N 0.93(3)
N2 C4 1.468(4)
N3 C6 1.478(4)
C1 C2 1.499(4)
C2 C3 1.381(4)
C2 C7 1.388(4)
C3 C4 1.385(4)
C3 H3 0.9300
C4 C5 1.366(4)
C5 C6 1.387(5)
C5 H5 0.9300
C6 C7 1.372(4)
C7 H7 0.9300
C8 C9 1.385(4)
C8 C13 1.387(4)
C9 C10 1.380(5)
C9 H9 0.9300
C10 C11 1.381(5)
C10 H10 0.9300
C11 C12 1.371(5)
C12 C13 1.388(4)
C12 H12 0.9300
C13 H13 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
N1 H1N O1 4_666 0.93(3) 1.93(3) 2.818(3) 159(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 2109590
