#------------------------------------------------------------------------------
#$Date: 2023-12-01 05:09:01 +0200 (Fri, 01 Dec 2023) $
#$Revision: 287918 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/29/2022951.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_2022951
loop_
_publ_author_name
'Richter, Adrian'
'Goddard, Richard'
'Imming, Peter'
'Seidel, Rüdiger W.'
_publ_section_title
;
 Crystal structure and antimycobacterial evaluation of
 2-(cyclohexylmethyl)-7-nitro-5-(trifluoromethyl)benzo[d]isothiazol-3(2H)-one
;
_journal_coeditor_code           VM2292
_journal_issue                   12
_journal_name_full
'Acta Crystallographica Section E Crystallographic Communications'
_journal_page_first              1194
_journal_page_last               1198
_journal_paper_doi               10.1107/S2056989023010137
_journal_volume                  79
_journal_year                    2023
_chemical_formula_iupac          'C15 H15 F3 N2 O3 S'
_chemical_formula_moiety         'C15 H15 F3 N2 O3 S'
_chemical_formula_sum            'C15 H15 F3 N2 O3 S'
_chemical_formula_weight         360.35
_chemical_name_systematic
2-(Cyclohexylmethyl)-7-nitro-5-(trifluoromethyl)benzo[d]isothiazol-3(2H)-one
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2019/3
_cell_angle_alpha                90
_cell_angle_beta                 93.633(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   21.9709(15)
_cell_length_b                   5.1271(4)
_cell_length_c                   27.022(2)
_cell_measurement_reflns_used    9947
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.37
_cell_measurement_theta_min      2.47
_cell_volume                     3037.8(4)
_computing_cell_refinement
;
SAINT (Bruker, 2004)
;
_computing_data_collection
;
APEX3 (Bruker, 2017)
;
_computing_data_reduction
;
SAINT (Bruker, 2004)
;
_computing_molecular_graphics
;
DIAMOND (Brandenburg, 2018)
;
_computing_publication_material
;
enCIFer (Allen et al.,  2004) and publCIF (Westrip,
2010)
;
_computing_structure_refinement
;
SHELXL2019/3 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT2014/5 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 66.67
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker Kappa Mach3 APEXII'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'Incoatec Helios mirrors'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0996
_diffrn_reflns_av_unetI/netI     0.0435
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            61976
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.495
_diffrn_reflns_theta_min         1.510
_diffrn_source                   'microfocus X-ray source'
_exptl_absorpt_coefficient_mu    0.265
_exptl_absorpt_correction_T_max  0.99220
_exptl_absorpt_correction_T_min  0.96726
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
(SADABS; Krause et al.,  2015)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.576
_exptl_crystal_description       needle
_exptl_crystal_F_000             1488
_exptl_crystal_size_max          0.195
_exptl_crystal_size_mid          0.061
_exptl_crystal_size_min          0.057
_refine_diff_density_max         0.340
_refine_diff_density_min         -0.330
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2836
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0587
_refine_ls_R_factor_gt           0.0422
_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)+(0.0554P)²+5.9357P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1036
_refine_ls_wR_factor_ref         0.1162
_reflns_number_gt                2243
_reflns_number_total             2836
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            vm2292sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'I 2/a'
_cod_database_code               2022951
_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   0.950
_shelx_estimated_absorpt_t_max   0.985
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -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_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C3 0.18859(9) 0.1371(5) 0.21632(9) 0.0197(5) Uani d 1 . .
C C3A 0.15790(10) 0.1247(5) 0.26275(8) 0.0183(5) Uani d 1 . .
C C4 0.16991(10) -0.0481(5) 0.30149(9) 0.0197(5) Uani d 1 . .
H H4 0.201655 -0.173215 0.300101 0.024 Uiso calc 1 . .
C C5 0.13485(10) -0.0359(5) 0.34241(9) 0.0198(5) Uani d 1 . .
C C6 0.08669(10) 0.1406(5) 0.34402(9) 0.0202(5) Uani d 1 . .
H H6 0.061716 0.142709 0.371460 0.024 Uiso calc 1 . .
C C7 0.07599(10) 0.3113(5) 0.30523(9) 0.0196(5) Uani d 1 . .
C C7A 0.11180(9) 0.3127(5) 0.26458(8) 0.0186(5) Uani d 1 . .
C C8 0.14904(10) -0.2056(5) 0.38629(9) 0.0217(5) Uani d 1 . .
C C9 0.18439(10) 0.4007(5) 0.13941(8) 0.0207(5) Uani d 1 . .
H H9A 0.227784 0.350627 0.138129 0.025 Uiso calc 1 . .
H H9B 0.181497 0.591480 0.134170 0.025 Uiso calc 1 . .
C C10 0.14732(10) 0.2631(5) 0.09739(8) 0.0209(5) Uani d 1 . .
H H10 0.141760 0.077299 0.107440 0.025 Uiso calc 1 . .
C C11 0.08388(10) 0.3832(5) 0.08715(9) 0.0234(5) Uani d 1 . .
H H11A 0.060785 0.370255 0.117343 0.028 Uiso calc 1 . .
H H11B 0.088125 0.570227 0.078966 0.028 Uiso calc 1 . .
C C12 0.04881(10) 0.2450(6) 0.04447(9) 0.0278(6) Uani d 1 . .
H H12A 0.041006 0.062157 0.053996 0.033 Uiso calc 1 . .
H H12B 0.008923 0.331937 0.037643 0.033 Uiso calc 1 . .
C C13 0.08402(11) 0.2483(6) -0.00212(9) 0.0283(6) Uani d 1 . .
H H13A 0.088292 0.430440 -0.013581 0.034 Uiso calc 1 . .
H H13B 0.061107 0.149498 -0.028697 0.034 Uiso calc 1 . .
C C14 0.14704(11) 0.1280(6) 0.00764(9) 0.0278(6) Uani d 1 . .
H H14A 0.142728 -0.059395 0.015561 0.033 Uiso calc 1 . .
H H14B 0.169975 0.141924 -0.022619 0.033 Uiso calc 1 . .
C C15 0.18246(10) 0.2642(5) 0.05047(9) 0.0245(6) Uani d 1 . .
H H15A 0.190777 0.446672 0.040981 0.029 Uiso calc 1 . .
H H15B 0.222109 0.175301 0.057240 0.029 Uiso calc 1 . .
N N1 0.02611(9) 0.4958(4) 0.30532(8) 0.0226(5) Uani d 1 . .
N N2 0.16422(8) 0.3389(4) 0.18865(7) 0.0207(5) Uani d 1 . .
O O1 0.22911(7) -0.0059(4) 0.20281(6) 0.0246(4) Uani d 1 . .
O O2 0.02475(7) 0.6650(3) 0.27241(6) 0.0258(4) Uani d 1 . .
O O3 -0.01168(8) 0.4766(4) 0.33673(7) 0.0300(4) Uani d 1 . .
F F1 0.18323(6) -0.4115(3) 0.37631(5) 0.0285(4) Uani d 1 . .
F F2 0.17958(7) -0.0767(3) 0.42334(5) 0.0310(4) Uani d 1 . .
F F3 0.09820(6) -0.2979(3) 0.40528(5) 0.0289(4) Uani d 1 . .
S S1 0.10703(2) 0.51050(12) 0.21373(2) 0.02003(18) Uani 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 0.0033 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'
F F 0.0171 0.0103 '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_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1.00 1.00 -1.00 0.0850
-1.00 -1.00 1.00 0.0850
1.00 0.00 1.00 0.0200
0.00 0.00 -1.00 0.0050
-1.00 0.00 1.00 0.0300
-2.00 -1.00 0.00 0.0750
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 C3 N2 . . 123.8(2) ?
O1 C3 C3A . . 127.7(2) ?
N2 C3 C3A . . 108.44(19) yes
C4 C3A C7A . . 121.2(2) yes
C4 C3A C3 . . 126.9(2) yes
C7A C3A C3 . . 112.0(2) yes
C3A C4 C5 . . 119.0(2) ?
C3A C4 H4 . . 120.5 ?
C5 C4 H4 . . 120.5 ?
C4 C5 C6 . . 121.0(2) ?
C4 C5 C8 . . 120.6(2) ?
C6 C5 C8 . . 118.4(2) ?
C7 C6 C5 . . 118.9(2) ?
C7 C6 H6 . . 120.6 ?
C5 C6 H6 . . 120.6 ?
C6 C7 C7A . . 121.8(2) yes
C6 C7 N1 . . 120.5(2) ?
C7A C7 N1 . . 117.6(2) ?
C7 C7A C3A . . 118.1(2) yes
C7 C7A S1 . . 129.07(18) ?
C3A C7A S1 . . 112.84(18) yes
F1 C8 F2 . . 106.21(18) ?
F1 C8 F3 . . 106.9(2) ?
F2 C8 F3 . . 106.07(18) ?
F1 C8 C5 . . 113.21(19) ?
F2 C8 C5 . . 112.1(2) ?
F3 C8 C5 . . 111.90(18) ?
N2 C9 C10 . . 113.45(19) ?
N2 C9 H9A . . 108.9 ?
C10 C9 H9A . . 108.9 ?
N2 C9 H9B . . 108.9 ?
C10 C9 H9B . . 108.9 ?
H9A C9 H9B . . 107.7 ?
C15 C10 C9 . . 109.99(19) ?
C15 C10 C11 . . 110.53(19) yes
C9 C10 C11 . . 112.6(2) ?
C15 C10 H10 . . 107.8 ?
C9 C10 H10 . . 107.8 ?
C11 C10 H10 . . 107.8 ?
C12 C11 C10 . . 111.2(2) yes
C12 C11 H11A . . 109.4 ?
C10 C11 H11A . . 109.4 ?
C12 C11 H11B . . 109.4 ?
C10 C11 H11B . . 109.4 ?
H11A C11 H11B . . 108.0 ?
C13 C12 C11 . . 111.3(2) yes
C13 C12 H12A . . 109.4 ?
C11 C12 H12A . . 109.4 ?
C13 C12 H12B . . 109.4 ?
C11 C12 H12B . . 109.4 ?
H12A C12 H12B . . 108.0 ?
C12 C13 C14 . . 110.9(2) yes
C12 C13 H13A . . 109.5 ?
C14 C13 H13A . . 109.5 ?
C12 C13 H13B . . 109.5 ?
C14 C13 H13B . . 109.5 ?
H13A C13 H13B . . 108.0 ?
C15 C14 C13 . . 111.2(2) yes
C15 C14 H14A . . 109.4 ?
C13 C14 H14A . . 109.4 ?
C15 C14 H14B . . 109.4 ?
C13 C14 H14B . . 109.4 ?
H14A C14 H14B . . 108.0 ?
C14 C15 C10 . . 111.6(2) yes
C14 C15 H15A . . 109.3 ?
C10 C15 H15A . . 109.3 ?
C14 C15 H15B . . 109.3 ?
C10 C15 H15B . . 109.3 ?
H15A C15 H15B . . 108.0 ?
O3 N1 O2 . . 124.3(2) ?
O3 N1 C7 . . 119.6(2) ?
O2 N1 C7 . . 116.06(19) ?
C3 N2 C9 . . 122.1(2) ?
C3 N2 S1 . . 116.46(16) yes
C9 N2 S1 . . 121.45(16) yes
C7A S1 N2 . . 90.24(10) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C3 O1 . 1.226(3) yes
C3 N2 . 1.366(3) yes
C3 C3A . 1.463(3) yes
C3A C4 . 1.384(3) yes
C3A C7A . 1.402(3) yes
C4 C5 . 1.388(3) yes
C4 H4 . 0.9500 ?
C5 C6 . 1.395(3) yes
C5 C8 . 1.488(3) yes
C6 C7 . 1.374(3) yes
C6 H6 . 0.9500 ?
C7 C7A . 1.391(3) yes
C7 N1 . 1.448(3) yes
C7A S1 . 1.706(2) yes
C8 F1 . 1.333(3) ?
C8 F2 . 1.343(3) ?
C8 F3 . 1.345(3) ?
C9 N2 . 1.464(3) ?
C9 C10 . 1.528(3) ?
C9 H9A . 0.9900 ?
C9 H9B . 0.9900 ?
C10 C15 . 1.526(3) ?
C10 C11 . 1.533(3) ?
C10 H10 . 1.0000 ?
C11 C12 . 1.521(3) ?
C11 H11A . 0.9900 ?
C11 H11B . 0.9900 ?
C12 C13 . 1.519(3) ?
C12 H12A . 0.9900 ?
C12 H12B . 0.9900 ?
C13 C14 . 1.523(3) ?
C13 H13A . 0.9900 ?
C13 H13B . 0.9900 ?
C14 C15 . 1.523(3) ?
C14 H14A . 0.9900 ?
C14 H14B . 0.9900 ?
C15 H15A . 0.9900 ?
C15 H15B . 0.9900 ?
N1 O3 . 1.228(3) ?
N1 O2 . 1.241(3) ?
N2 S1 . 1.709(2) ?
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
C4 H4 O1 7_545 0.95 2.25 3.193(3) 175 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O1 C3 C3A C4 . . . . 2.0(4) ?
N2 C3 C3A C4 . . . . -178.5(2) ?
O1 C3 C3A C7A . . . . -177.3(2) ?
N2 C3 C3A C7A . . . . 2.3(3) ?
C7A C3A C4 C5 . . . . 0.9(3) ?
C3 C3A C4 C5 . . . . -178.2(2) ?
C3A C4 C5 C6 . . . . 2.4(3) ?
C3A C4 C5 C8 . . . . -175.7(2) ?
C4 C5 C6 C7 . . . . -2.8(3) ?
C8 C5 C6 C7 . . . . 175.3(2) ?
C5 C6 C7 C7A . . . . 0.0(3) ?
C5 C6 C7 N1 . . . . 179.4(2) ?
C6 C7 C7A C3A . . . . 3.2(3) ?
N1 C7 C7A C3A . . . . -176.3(2) ?
C6 C7 C7A S1 . . . . -178.69(19) ?
N1 C7 C7A S1 . . . . 1.9(3) ?
C4 C3A C7A C7 . . . . -3.6(3) ?
C3 C3A C7A C7 . . . . 175.6(2) ?
C4 C3A C7A S1 . . . . 177.93(18) ?
C3 C3A C7A S1 . . . . -2.8(2) ?
C4 C5 C8 F1 . . . . -19.4(3) ?
C6 C5 C8 F1 . . . . 162.4(2) ?
C4 C5 C8 F2 . . . . 100.7(3) ?
C6 C5 C8 F2 . . . . -77.5(3) ?
C4 C5 C8 F3 . . . . -140.3(2) ?
C6 C5 C8 F3 . . . . 41.5(3) ?
N2 C9 C10 C15 . . . . -161.7(2) ?
N2 C9 C10 C11 . . . . 74.5(3) ?
C15 C10 C11 C12 . . . . 55.4(3) ?
C9 C10 C11 C12 . . . . 178.9(2) ?
C10 C11 C12 C13 . . . . -56.3(3) ?
C11 C12 C13 C14 . . . . 56.3(3) ?
C12 C13 C14 C15 . . . . -55.7(3) ?
C13 C14 C15 C10 . . . . 55.6(3) ?
C9 C10 C15 C14 . . . . 179.9(2) ?
C11 C10 C15 C14 . . . . -55.2(3) ?
C6 C7 N1 O3 . . . . -9.8(3) ?
C7A C7 N1 O3 . . . . 169.7(2) ?
C6 C7 N1 O2 . . . . 170.6(2) ?
C7A C7 N1 O2 . . . . -9.9(3) ?
O1 C3 N2 C9 . . . . 0.7(3) ?
C3A C3 N2 C9 . . . . -178.87(19) ?
O1 C3 N2 S1 . . . . 178.73(18) ?
C3A C3 N2 S1 . . . . -0.8(2) ?
C10 C9 N2 C3 . . . . 91.3(3) ?
C10 C9 N2 S1 . . . . -86.6(2) ?
C7 C7A S1 N2 . . . . -176.2(2) ?
C3A C7A S1 N2 . . . . 1.96(17) ?
C3 N2 S1 C7A . . . . -0.63(18) ?
C9 N2 S1 C7A . . . . 177.45(19) ?

_cod_database_fobs_code 2022951
