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#$Date: 2023-01-28 10:42:34 +0200 (Sat, 28 Jan 2023) $
#$Revision: 280651 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/66/8106610.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_8106610
loop_
_publ_author_name
'Liu, Li'
'Wu, Ming-Yuan'
'Huang, Chao'
'Teng, Ming-Gang'
'Cao, Jian-Xin'
_publ_section_title
;
 The crystal structure of
 4-bromo-N-cyclopropyl-2,5-difluorobenzenesulfonamide, C9H8BrF2NO2S
;
_journal_issue                   4
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              585
_journal_page_last               586
_journal_paper_doi               10.1515/ncrs-2016-0352
_journal_volume                  232
_journal_year                    2017
_chemical_formula_sum            'C9 H8 Br F2 N O2 S'
_chemical_formula_weight         312.13
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_cell_angle_alpha                92.637(3)
_cell_angle_beta                 111.201(2)
_cell_angle_gamma                105.856(2)
_cell_formula_units_Z            2
_cell_length_a                   7.5277(6)
_cell_length_b                   8.3730(7)
_cell_length_c                   9.8785(9)
_cell_measurement_reflns_used    1258
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      24.64
_cell_measurement_theta_min      2.56
_cell_volume                     551.08(8)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  CCD
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0201
_diffrn_reflns_av_unetI/netI     0.0341
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            3574
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.077
_diffrn_reflns_theta_max         25.077
_diffrn_reflns_theta_min         2.241
_exptl_absorpt_coefficient_mu    3.930
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.881
_exptl_crystal_description       Block
_exptl_crystal_F_000             308
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.150
_exptl_transmission_factor_max   0.864
_exptl_transmission_factor_min   0.864
_refine_diff_density_max         0.263
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.076
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     149
_refine_ls_number_reflns         1940
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0444
_refine_ls_R_factor_gt           0.0330
_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)+(0.0383P)²+0.1016P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0741
_refine_ls_wR_factor_ref         0.0787
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1580
_reflns_number_total             1940
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2016-0352_suppl.cif
_cod_data_source_block           1
_cod_database_code               8106610
_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   0.479
_shelx_estimated_absorpt_t_max   0.590
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
H1N H 0.657(5) 0.053(4) 0.430(3) 0.030(9) Uiso 1 1 d . . . . .
Br1 Br 0.05704(5) 0.39942(5) -0.18303(4) 0.05545(17) Uani 1 1 d . . . . .
C1 C 0.2215(4) 0.3637(4) 0.0009(4) 0.0380(8) Uani 1 1 d . . . . .
C2 C 0.3573(5) 0.4963(4) 0.1075(4) 0.0383(8) Uani 1 1 d . . . . .
C3 C 0.4746(5) 0.4730(4) 0.2439(3) 0.0348(7) Uani 1 1 d . . . . .
H3 H 0.5662 0.5647 0.3145 0.042 Uiso 1 1 calc R U . . .
C4 C 0.4544(4) 0.3107(4) 0.2745(3) 0.0298(7) Uani 1 1 d . . . . .
C5 C 0.3187(4) 0.1787(4) 0.1658(4) 0.0351(7) Uani 1 1 d . . . . .
C6 C 0.2025(4) 0.2011(4) 0.0290(4) 0.0391(8) Uani 1 1 d . . . . .
H6 H 0.1136 0.1095 -0.0428 0.047 Uiso 1 1 calc R U . . .
N1 N 0.7084(4) 0.1475(4) 0.4356(3) 0.0372(7) Uani 1 1 d . . . . .
C8 C 0.8632(5) 0.1845(4) 0.3784(4) 0.0478(9) Uani 1 1 d . . . . .
H8 H 0.9786 0.2844 0.4309 0.057 Uiso 1 1 calc R U . . .
C9 C 0.9092(6) 0.0406(5) 0.3220(4) 0.0568(10) Uani 1 1 d . . . . .
H9A H 0.8276 -0.0718 0.3207 0.068 Uiso 1 1 calc R U . . .
H9B H 1.0486 0.0525 0.3421 0.068 Uiso 1 1 calc R U . . .
C10 C 0.8129(7) 0.1440(6) 0.2191(5) 0.0738(14) Uani 1 1 d . . . . .
H10A H 0.8935 0.2190 0.1765 0.089 Uiso 1 1 calc R U . . .
H10B H 0.6726 0.0946 0.1550 0.089 Uiso 1 1 calc R U . . .
O1 O 0.7408(3) 0.4390(3) 0.5240(2) 0.0443(6) Uani 1 1 d . . . . .
O2 O 0.4574(3) 0.1985(3) 0.5154(3) 0.0425(5) Uani 1 1 d . . . . .
F1 F 0.2979(3) 0.0193(2) 0.1936(2) 0.0539(5) Uani 1 1 d . . . . .
F2 F 0.3769(3) 0.6550(2) 0.0794(2) 0.0594(6) Uani 1 1 d . . . . .
S1 S 0.59626(11) 0.27917(9) 0.45233(8) 0.0328(2) Uani 1 1 d . . . . .
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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'
F F 0.0171 0.0103 '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
C2 C1 C6 119.7(3) . .
C2 C1 Br1 121.1(2) . .
C6 C1 Br1 119.2(2) . .
F2 C2 C1 119.6(3) . .
F2 C2 C3 118.5(3) . .
C1 C2 C3 121.9(3) . .
C2 C3 C4 119.0(3) . .
C2 C3 H3 120.5 . .
C4 C3 H3 120.5 . .
C5 C4 C3 118.4(3) . .
C5 C4 S1 122.1(2) . .
C3 C4 S1 119.5(2) . .
F1 C5 C6 118.0(3) . .
F1 C5 C4 119.2(3) . .
C6 C5 C4 122.9(3) . .
C5 C6 C1 118.1(3) . .
C5 C6 H6 121.0 . .
C1 C6 H6 121.0 . .
C8 N1 S1 122.4(2) . .
C8 N1 H1N 114(2) . .
S1 N1 H1N 120(2) . .
N1 C8 C9 117.5(3) . .
N1 C8 C10 120.6(3) . .
C9 C8 C10 60.2(3) . .
N1 C8 H8 115.7 . .
C9 C8 H8 115.7 . .
C10 C8 H8 115.7 . .
C8 C9 C10 59.9(3) . .
C8 C9 H9A 117.8 . .
C10 C9 H9A 117.8 . .
C8 C9 H9B 117.8 . .
C10 C9 H9B 117.8 . .
H9A C9 H9B 114.9 . .
C8 C10 C9 59.9(3) . .
C8 C10 H10A 117.8 . .
C9 C10 H10A 117.8 . .
C8 C10 H10B 117.8 . .
C9 C10 H10B 117.8 . .
H10A C10 H10B 114.9 . .
O1 S1 O2 119.56(15) . .
O1 S1 N1 109.50(15) . .
O2 S1 N1 105.86(14) . .
O1 S1 C4 105.52(13) . .
O2 S1 C4 107.46(14) . .
N1 S1 C4 108.58(14) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 C1 1.884(3) .
C1 C2 1.372(5) .
C1 C6 1.381(4) .
C2 F2 1.350(3) .
C2 C3 1.375(4) .
C3 C4 1.385(4) .
C3 H3 0.9300 .
C4 C5 1.378(4) .
C4 S1 1.771(3) .
C5 F1 1.354(3) .
C5 C6 1.373(4) .
C6 H6 0.9300 .
N1 C8 1.438(4) .
N1 S1 1.596(3) .
N1 H1N 0.77(3) .
C8 C9 1.479(5) .
C8 C10 1.478(6) .
C8 H8 0.9800 .
C9 C10 1.483(5) .
C9 H9A 0.9700 .
C9 H9B 0.9700 .
C10 H10A 0.9700 .
C10 H10B 0.9700 .
O1 S1 1.427(2) .
O2 S1 1.435(2) .
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
C6 C1 C2 F2 179.4(3) . . . .
Br1 C1 C2 F2 -1.5(4) . . . .
C6 C1 C2 C3 -1.0(5) . . . .
Br1 C1 C2 C3 178.1(2) . . . .
F2 C2 C3 C4 179.4(3) . . . .
C1 C2 C3 C4 -0.2(5) . . . .
C2 C3 C4 C5 0.9(4) . . . .
C2 C3 C4 S1 -177.2(2) . . . .
C3 C4 C5 F1 179.6(3) . . . .
S1 C4 C5 F1 -2.3(4) . . . .
C3 C4 C5 C6 -0.3(5) . . . .
S1 C4 C5 C6 177.7(2) . . . .
F1 C5 C6 C1 179.1(3) . . . .
C4 C5 C6 C1 -0.9(5) . . . .
C2 C1 C6 C5 1.6(5) . . . .
Br1 C1 C6 C5 -177.6(2) . . . .
S1 N1 C8 C9 -160.3(3) . . . .
S1 N1 C8 C10 -90.3(4) . . . .
N1 C8 C9 C10 111.3(4) . . . .
N1 C8 C10 C9 -106.2(4) . . . .
C8 N1 S1 O1 -48.6(3) . . . .
C8 N1 S1 O2 -178.8(3) . . . .
C8 N1 S1 C4 66.1(3) . . . .
C5 C4 S1 O1 170.5(3) . . . .
C3 C4 S1 O1 -11.5(3) . . . .
C5 C4 S1 O2 -60.9(3) . . . .
C3 C4 S1 O2 117.1(2) . . . .
C5 C4 S1 N1 53.2(3) . . . .
C3 C4 S1 N1 -128.8(2) . . . .
