#------------------------------------------------------------------------------
#$Date: 2017-07-25 12:27:26 +0300 (Tue, 25 Jul 2017) $
#$Revision: 199121 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/08/2020831.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_2020831
loop_
_publ_author_name
'Naveen, S.'
'Sudha, A. G.'
'Suresha, E.'
'Lokanath, N. K.'
'Suchetan, P. A.'
'Abdoh, M.'
_publ_section_title
;
 Crystal structures of isomeric
 4-bromo-N-[(2-nitrophenyl)sulfonyl]benzamide and
 4-bromo-N-[(4-nitrophenyl)sulfonyl]benzamide
;
_journal_issue                   3
_journal_name_full
'Acta Crystallographica Section E Crystallographic Communications'
_journal_page_first              314
_journal_paper_doi               10.1107/S2056989017001578
_journal_volume                  73
_journal_year                    2017
_chemical_formula_iupac          'C13 H9 Br N2 O5 S'
_chemical_formula_moiety         'C13 H9 Br N2 O5 S'
_chemical_formula_sum            'C13 H9 Br N2 O5 S'
_chemical_formula_weight         385.19
_chemical_melting_point          498
_chemical_name_systematic
;
4-Bromo-N-[(4-nitrophenyl)sulfonyl]benzamide
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2016/4
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.6085(4)
_cell_length_b                   10.3246(5)
_cell_length_c                   27.7296(13)
_cell_measurement_reflns_used    195
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      64.4
_cell_measurement_theta_min      3.2
_cell_volume                     2750.9(2)
_computing_cell_refinement
;
APEX2 and SAINT-Plus (Bruker, 2009)
;
_computing_data_collection
;
APEX2 (Bruker, 2009)
;
_computing_data_reduction
;
SAINT-Plus and XPREP (Bruker, 2009)
;
_computing_molecular_graphics
;
Mercury (Macrae et al.,  2008)
;
_computing_publication_material
;
SHELXL2016 (Sheldrick, 2015b)
;
_computing_structure_refinement
;
SHELXL2016 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT2014 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'Bruker APEXII'
_diffrn_measurement_method       'phi and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0547
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            12896
_diffrn_reflns_theta_full        64.442
_diffrn_reflns_theta_max         64.442
_diffrn_reflns_theta_min         3.187
_diffrn_standards_decay_%        1
_diffrn_standards_interval_count 1
_diffrn_standards_number         1
_exptl_absorpt_coefficient_mu    5.761
_exptl_absorpt_correction_T_max  0.631
_exptl_absorpt_correction_T_min  0.491
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2009)
;
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.860
_exptl_crystal_description       Prism
_exptl_crystal_F_000             1536
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.080
_refine_diff_density_max         1.098
_refine_diff_density_min         -1.686
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.124
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         2256
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.124
_refine_ls_R_factor_all          0.0504
_refine_ls_R_factor_gt           0.0499
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0950P)²+3.3998P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1374
_refine_ls_wR_factor_ref         0.1380
_reflns_number_gt                2221
_reflns_number_total             2256
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            hb7646sup1.cif
_cod_data_source_block           II
_cod_database_code               2020831
_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   0.364
_shelx_estimated_absorpt_t_max   0.656
loop_
_space_group_symop_operation_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_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 0.84255(4) 0.07764(3) 0.93310(2) 0.0173(2) Uani d 1
S S1 0.64837(8) 0.55824(8) 0.68971(3) 0.0106(3) Uani d 1
O O3 0.9065(2) 0.41915(19) 0.72287(8) 0.0121(5) Uani d 1
O O1 0.7620(2) 0.6467(2) 0.68874(7) 0.0150(5) Uani d 1
O O2 0.5095(2) 0.6044(2) 0.69698(8) 0.0142(5) Uani d 1
O O4 0.5406(3) 0.2713(3) 0.47917(8) 0.0329(7) Uani d 1
O O5 0.7105(3) 0.1538(3) 0.50614(9) 0.0336(7) Uani d 1
N N1 0.6740(3) 0.4527(3) 0.73423(10) 0.0109(6) Uani d 1
N N2 0.6290(3) 0.2439(3) 0.50936(10) 0.0226(7) Uani d 1
C C8 0.8049(3) 0.3267(3) 0.79323(11) 0.0118(6) Uani d 1
C C9 0.9167(3) 0.2414(3) 0.79975(11) 0.0123(6) Uani d 1
H H9 0.985687 0.233663 0.775389 0.015 Uiso calc 1
C C13 0.7045(3) 0.3383(3) 0.82959(11) 0.0120(6) Uani d 1
H H13 0.628340 0.395897 0.825434 0.014 Uiso calc 1
C C10 0.9273(3) 0.1686(3) 0.84136(11) 0.0145(6) Uani d 1
H H10 1.002921 0.110502 0.845651 0.017 Uiso calc 1
C C12 0.7156(3) 0.2662(3) 0.87166(11) 0.0138(7) Uani d 1
H H12 0.648375 0.274796 0.896577 0.017 Uiso calc 1
C C5 0.5224(4) 0.4010(4) 0.56487(11) 0.0175(8) Uani d 1
H H5 0.442958 0.404706 0.544537 0.021 Uiso calc 1
C C4 0.6369(3) 0.3257(3) 0.55290(12) 0.0161(7) Uani d 1
C C7 0.8014(3) 0.4021(3) 0.74789(12) 0.0123(7) Uani d 1
C C6 0.5281(3) 0.4704(3) 0.60744(11) 0.0156(7) Uani d 1
H H6 0.450494 0.520542 0.617544 0.019 Uiso calc 1
C C11 0.8268(3) 0.1812(3) 0.87667(11) 0.0133(7) Uani d 1
C C3 0.7578(3) 0.3213(3) 0.58033(13) 0.0190(7) Uani d 1
H H3 0.834325 0.269078 0.570736 0.023 Uiso calc 1
C C2 0.7638(4) 0.3946(3) 0.62190(11) 0.0172(7) Uani d 1
H H2 0.845796 0.395971 0.641024 0.021 Uiso calc 1
C C1 0.6477(3) 0.4665(3) 0.63527(11) 0.0117(7) Uani d 1
H HN1 0.593(4) 0.430(3) 0.7485(14) 0.015(11) Uiso 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 '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
O1 S1 O2 120.29(14)
O1 S1 N1 108.68(14)
O2 S1 N1 104.55(14)
O1 S1 C1 109.13(14)
O2 S1 C1 107.02(14)
N1 S1 C1 106.33(16)
C7 N1 S1 125.5(2)
C7 N1 HN1 123(2)
S1 N1 HN1 112(2)
O5 N2 O4 124.8(3)
O5 N2 C4 117.6(3)
O4 N2 C4 117.5(3)
C13 C8 C9 119.3(3)
C13 C8 C7 123.4(3)
C9 C8 C7 117.3(3)
C10 C9 C8 120.4(3)
C10 C9 H9 119.8
C8 C9 H9 119.8
C12 C13 C8 120.4(3)
C12 C13 H13 119.8
C8 C13 H13 119.8
C11 C10 C9 119.3(3)
C11 C10 H10 120.3
C9 C10 H10 120.3
C13 C12 C11 118.8(3)
C13 C12 H12 120.6
C11 C12 H12 120.6
C6 C5 C4 117.6(3)
C6 C5 H5 121.2
C4 C5 H5 121.2
C5 C4 C3 123.4(3)
C5 C4 N2 118.4(3)
C3 C4 N2 118.2(3)
O3 C7 N1 121.0(3)
O3 C7 C8 122.2(3)
N1 C7 C8 116.8(3)
C5 C6 C1 119.6(3)
C5 C6 H6 120.2
C1 C6 H6 120.2
C10 C11 C12 121.7(3)
C10 C11 BR1 118.4(2)
C12 C11 BR1 119.9(2)
C2 C3 C4 118.3(3)
C2 C3 H3 120.8
C4 C3 H3 120.8
C3 C2 C1 118.8(3)
C3 C2 H2 120.6
C1 C2 H2 120.6
C6 C1 C2 122.2(3)
C6 C1 S1 117.4(2)
C2 C1 S1 120.4(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
BR1 C11 1.901(3)
S1 O1 1.424(2)
S1 O2 1.431(2)
S1 N1 1.665(3)
S1 C1 1.782(3)
O3 C7 1.238(4)
O4 N2 1.226(4)
O5 N2 1.219(4)
N1 C7 1.384(4)
N1 HN1 0.90(4)
N2 C4 1.475(4)
C8 C13 1.400(4)
C8 C9 1.400(5)
C8 C7 1.479(4)
C9 C10 1.381(4)
C9 H9 0.9500
C13 C12 1.388(4)
C13 H13 0.9500
C10 C11 1.381(4)
C10 H10 0.9500
C12 C11 1.390(4)
C12 H12 0.9500
C5 C6 1.382(5)
C5 C4 1.387(5)
C5 H5 0.9500
C4 C3 1.389(5)
C6 C1 1.384(4)
C6 H6 0.9500
C3 C2 1.380(5)
C3 H3 0.9500
C2 C1 1.390(5)
C2 H2 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
N1 HN1 O3 6_455 0.90 1.97 2.8530 168
C2 H2 O3 1_555 0.95 2.36 3.1280 138
C3 H3 O4 3_556 0.95 2.45 3.3199 152
C9 H9 O2 7_555 0.95 2.55 3.2599 132
C10 H10 O1 4_655 0.95 2.48 3.1081 124
C12 H12 O4 8_554 0.95 2.56 3.4445 155
C13 H13 O3 6_455 0.95 2.53 3.3182 141

_cod_database_fobs_code 2020831
