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#$Date: 2023-09-18 10:42:31 +0300 (Mon, 18 Sep 2023) $
#$Revision: 286379 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/75/8107506.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_8107506
loop_
_publ_author_name
'Jie, Wang'
'Xiao, Shu-Zhen'
'Cong, Huang'
'Liu, Ya-Qiang'
'Peng, Da-Yong'
_publ_section_title
;
 5-Amino-2-chloro-4-fluoro-N-(N-isopropyl-N-methylsulfamoyl) benzamide,
 C11H15O3ClFN3S
;
_journal_issue                   4
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              597
_journal_page_last               598
_journal_paper_doi               10.1515/ncrs-2023-0097
_journal_volume                  238
_journal_year                    2023
_chemical_formula_sum            'C11 H15 Cl F N3 O3 S'
_chemical_formula_weight         323.77
_chemical_name_systematic
;
5-amino-2-chloro-4-fluoro-N-(N-isopropyl-N-methylsulfamoyl) benzamide
;
_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   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                67.543(2)
_cell_angle_beta                 72.776(2)
_cell_angle_gamma                88.529(2)
_cell_formula_units_Z            2
_cell_length_a                   7.8107(11)
_cell_length_b                   9.1644(13)
_cell_length_c                   11.3521(15)
_cell_measurement_reflns_used    5862
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      31.61
_cell_measurement_theta_min      2.48
_cell_volume                     713.76(17)
_computing_cell_refinement       'APEX2, SAINT and SADABS [1]'
_computing_data_collection       'APEX2, SAINT and SADABS [1]'
_computing_data_reduction        'APEX2, SAINT and SADABS [1]'
_computing_molecular_graphics    'Diamond 4.0 [4]'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014) [2,3]'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014) [2,3]'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014) [2,3]'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0179
_diffrn_reflns_av_unetI/netI     0.0266
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5100
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.498
_diffrn_reflns_theta_min         2.042
_exptl_absorpt_coefficient_mu    0.435
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_diffrn    1.507
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.140
_refine_diff_density_max         0.394
_refine_diff_density_min         -0.398
_refine_diff_density_rms         0.116
_refine_ls_extinction_coef       0.074(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.171
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         2628
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.171
_refine_ls_R_factor_all          0.0427
_refine_ls_R_factor_gt           0.0385
_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)+(0.0852P)²+0.1857P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1191
_refine_ls_wR_factor_ref         0.1338
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2438
_reflns_number_total             2628
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_j_ncrs-2023-0097_suppl_001.cif
_cod_data_source_block           mo_1_0m
_cod_database_code               8107506
_shelx_shelxl_version_number     2014/7
_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   0.954
_shelx_estimated_absorpt_t_max   0.970
_publcif_funding_html
;
;
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
C1 C 0.1410(3) 0.2849(2) 0.17707(19) 0.0341(4) Uani 1 1 d . . . . .
C2 C 0.1640(3) 0.2013(2) 0.08355(18) 0.0318(4) Uani 1 1 d . . . . .
C3 C 0.2357(3) 0.0560(2) 0.09844(19) 0.0333(4) Uani 1 1 d . . . . .
C4 C 0.2599(3) -0.0018(2) -0.0012(2) 0.0386(5) Uani 1 1 d . . . . .
H4 H 0.3088 -0.0975 0.0073 0.046 Uiso 1 1 calc R U . . .
C5 C 0.2106(3) 0.0845(3) -0.1124(2) 0.0412(5) Uani 1 1 d . . . . .
C6 C 0.1395(3) 0.2284(3) -0.1333(2) 0.0402(5) Uani 1 1 d . . . . .
C7 C 0.1160(3) 0.2841(2) -0.0312(2) 0.0367(4) Uani 1 1 d . . . . .
H7 H 0.0665 0.3798 -0.0404 0.044 Uiso 1 1 calc R U . . .
C8 C 0.3471(4) 0.5247(3) 0.3190(3) 0.0603(7) Uani 1 1 d . . . . .
H8A H 0.4492 0.5530 0.3394 0.090 Uiso 1 1 calc R U . . .
H8B H 0.2420 0.5634 0.3624 0.090 Uiso 1 1 calc R U . . .
H8C H 0.3689 0.5711 0.2238 0.090 Uiso 1 1 calc R U . . .
C9 C 0.5971(5) 0.3228(4) 0.2075(4) 0.0822(10) Uani 1 1 d . . . . .
H9A H 0.5273 0.3374 0.1477 0.123 Uiso 1 1 calc R U . . .
H9B H 0.6848 0.2502 0.1953 0.123 Uiso 1 1 calc R U . . .
H9C H 0.6573 0.4229 0.1886 0.123 Uiso 1 1 calc R U . . .
C10 C 0.4737(3) 0.2560(3) 0.3511(3) 0.0494(6) Uani 1 1 d . . . . .
H10 H 0.4261 0.1484 0.3712 0.059 Uiso 1 1 calc R U . . .
C11 C 0.5726(5) 0.2447(5) 0.4497(4) 0.0944(12) Uani 1 1 d . . . . .
H11A H 0.6182 0.3492 0.4337 0.142 Uiso 1 1 calc R U . . .
H11B H 0.6710 0.1812 0.4388 0.142 Uiso 1 1 calc R U . . .
H11C H 0.4915 0.1967 0.5394 0.142 Uiso 1 1 calc R U . . .
Cl1 Cl 0.31003(7) -0.05650(6) 0.23331(5) 0.0456(2) Uani 1 1 d . . . . .
F1 F 0.2336(2) 0.0272(2) -0.20975(15) 0.0616(4) Uani 1 1 d . . . . .
N1 N 0.0968(4) 0.3111(3) -0.2483(2) 0.0675(7) Uani 1 1 d . . . . .
H1A H 0.1142 0.2734 -0.3092 0.081 Uiso 1 1 calc R U . . .
H1B H 0.0526 0.4006 -0.2596 0.081 Uiso 1 1 calc R U . . .
N2 N 0.1042(2) 0.19277(19) 0.31098(15) 0.0332(4) Uani 1 1 d . . . . .
H2 H 0.0710 0.0934 0.3388 0.040 Uiso 1 1 calc R U . . .
N3 N 0.3185(2) 0.35139(19) 0.36715(19) 0.0393(4) Uani 1 1 d . . . . .
O1 O 0.1563(3) 0.42838(17) 0.13629(16) 0.0509(4) Uani 1 1 d . . . . .
O2 O -0.0062(2) 0.3760(2) 0.43120(18) 0.0515(4) Uani 1 1 d . . . . .
O3 O 0.1046(2) 0.12125(19) 0.53781(14) 0.0451(4) Uani 1 1 d . . . . .
S1 S 0.12054(6) 0.26391(6) 0.42230(4) 0.0331(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'
Cl Cl 0.1484 0.1585 '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'
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'
S S 0.1246 0.1234 '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
O1 C1 N2 120.99(18) . .
O1 C1 C2 121.55(18) . .
N2 C1 C2 117.45(16) . .
C7 C2 C3 118.86(18) . .
C7 C2 C1 114.59(17) . .
C3 C2 C1 126.47(17) . .
C4 C3 C2 119.92(18) . .
C4 C3 Cl1 116.11(15) . .
C2 C3 Cl1 123.87(15) . .
C5 C4 C3 118.91(18) . .
C5 C4 H4 120.5 . .
C3 C4 H4 120.5 . .
F1 C5 C4 118.78(18) . .
F1 C5 C6 117.19(18) . .
C4 C5 C6 124.02(18) . .
N1 C6 C5 121.3(2) . .
N1 C6 C7 122.7(2) . .
C5 C6 C7 116.04(18) . .
C2 C7 C6 122.23(19) . .
C2 C7 H7 118.9 . .
C6 C7 H7 118.9 . .
N3 C8 H8A 109.5 . .
N3 C8 H8B 109.5 . .
H8A C8 H8B 109.5 . .
N3 C8 H8C 109.5 . .
H8A C8 H8C 109.5 . .
H8B C8 H8C 109.5 . .
C10 C9 H9A 109.5 . .
C10 C9 H9B 109.5 . .
H9A C9 H9B 109.5 . .
C10 C9 H9C 109.5 . .
H9A C9 H9C 109.5 . .
H9B C9 H9C 109.5 . .
N3 C10 C11 110.8(2) . .
N3 C10 C9 110.6(2) . .
C11 C10 C9 112.1(3) . .
N3 C10 H10 107.7 . .
C11 C10 H10 107.7 . .
C9 C10 H10 107.7 . .
C10 C11 H11A 109.5 . .
C10 C11 H11B 109.5 . .
H11A C11 H11B 109.5 . .
C10 C11 H11C 109.5 . .
H11A C11 H11C 109.5 . .
H11B C11 H11C 109.5 . .
C6 N1 H1A 120.0 . .
C6 N1 H1B 120.0 . .
H1A N1 H1B 120.0 . .
C1 N2 S1 123.13(13) . .
C1 N2 H2 118.4 . .
S1 N2 H2 118.4 . .
C8 N3 C10 120.63(18) . .
C8 N3 S1 120.62(16) . .
C10 N3 S1 118.38(13) . .
O2 S1 O3 118.90(10) . .
O2 S1 N3 109.00(10) . .
O3 S1 N3 110.00(10) . .
O2 S1 N2 110.12(9) . .
O3 S1 N2 101.66(9) . .
N3 S1 N2 106.32(9) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 O1 1.211(2) .
C1 N2 1.371(2) .
C1 C2 1.499(3) .
C2 C7 1.391(3) .
C2 C3 1.401(3) .
C3 C4 1.386(3) .
C3 Cl1 1.7416(19) .
C4 C5 1.370(3) .
C4 H4 0.9300 .
C5 F1 1.360(2) .
C5 C6 1.380(3) .
C6 N1 1.371(3) .
C6 C7 1.399(3) .
C7 H7 0.9300 .
C8 N3 1.468(3) .
C8 H8A 0.9600 .
C8 H8B 0.9600 .
C8 H8C 0.9600 .
C9 C10 1.515(4) .
C9 H9A 0.9600 .
C9 H9B 0.9600 .
C9 H9C 0.9600 .
C10 N3 1.484(3) .
C10 C11 1.511(4) .
C10 H10 0.9800 .
C11 H11A 0.9600 .
C11 H11B 0.9600 .
C11 H11C 0.9600 .
N1 H1A 0.8600 .
N1 H1B 0.8600 .
N2 S1 1.6636(15) .
N2 H2 0.8600 .
N3 S1 1.5916(17) .
O2 S1 1.4185(17) .
O3 S1 1.4304(16) .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2 O3 0.86 2.15 2.950(2) 155.0 2_556
N2 H2 Cl1 0.86 2.57 3.0150(15) 113.2 .
N1 H1B O2 0.86 2.34 3.045(2) 139.8 2_565
N1 H1A O3 0.86 2.63 3.473(2) 168.0 1_554
C9 H9B F1 0.96 2.54 3.427(3) 153.9 2_655
C7 H7 O1 0.93 2.61 3.421(2) 146.1 2_565
