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#$Date: 2022-09-07 04:48:42 +0300 (Wed, 07 Sep 2022) $
#$Revision: 277702 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/41/2244158.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_2244158
loop_
_publ_author_name
'Schinke, Jascha'
'Gelbrich, Thomas'
'Griesser, Ulrich J.'
_publ_section_title
;
 Crystal structure, PIXEL calculations of intermolecular interaction
 energies and solid-state characterization of the herbicide isoxaflutole
;
_journal_coeditor_code           WM5659
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2056989022008647
_journal_volume                  78
_journal_year                    2022
_chemical_formula_iupac          'C15 H12 F3 N O4 S'
_chemical_formula_moiety         'C15 H12 F3 N O4 S'
_chemical_formula_sum            'C15 H12 F3 N O4 S'
_chemical_formula_weight         359.32
_chemical_name_common            isoxaflutole
_chemical_name_systematic
;
(5-Cyclopropyl-1,2-oxazol-4-yl)[2-(methylsulfonyl)-4-(trifluoromethyl)\
phenyl]methanone
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 118.530(15)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.5689(16)
_cell_length_b                   9.2906(8)
_cell_length_c                   13.4358(15)
_cell_measurement_reflns_used    2902
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      29.8150
_cell_measurement_theta_min      5.0110
_cell_volume                     1488.1(3)
_computing_cell_refinement
;
CrysAlisPro (Rigaku OD, 2020)
;
_computing_data_collection
;
CrysAlisPro (Rigaku OD, 2020)
;
_computing_data_reduction
;
CrysAlisPro (Rigaku OD, 2020)
;
_computing_molecular_graphics
;
XP (Bruker, 1998) and Mercury (Macrae et al.,  2020)
;
_computing_publication_material
;
PLATON (Spek, 2020) and publCIF Westrip (2010)
;
_computing_structure_refinement
;
SHELXL (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      193(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3575
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_av_unetI/netI     0.0385
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9962
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.103
_diffrn_reflns_theta_min         2.780
_diffrn_source                   'fine-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.273
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92448
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlisPro; Rigaku OD, 2020)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.604
_exptl_crystal_description       prism
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.309
_refine_diff_density_min         -0.354
_refine_ls_extinction_coef       0.0203(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    refU
_refine_ls_matrix_type           full
_refine_ls_number_parameters     231
_refine_ls_number_reflns         3275
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.0502
_refine_ls_R_factor_gt           0.0381
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0428P)²+0.6729P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0890
_refine_ls_wR_factor_ref         0.0973
_reflns_number_gt                2667
_reflns_number_total             3275
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            wm5659sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2244158
_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   0.935
_shelx_estimated_absorpt_t_max   0.978
_shelxl_version_number           2014/6
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'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
O O1 0.24820(10) 0.73141(14) 0.02968(10) 0.0294(3) Uani d 1 . .
N N2 0.32693(13) 0.75772(18) -0.01032(12) 0.0306(4) Uani d 1 . .
C C3 0.42144(15) 0.7107(2) 0.06926(14) 0.0258(4) Uani d 1 . .
H H3 0.4898 0.7158 0.0662 0.033(5) Uiso calc 1 . .
C C4 0.41253(14) 0.65039(18) 0.16220(13) 0.0217(4) Uani d 1 . .
C C5 0.30138(14) 0.66771(19) 0.13150(13) 0.0225(4) Uani d 1 . .
C C6 0.49824(14) 0.58226(19) 0.26500(14) 0.0242(4) Uani d 1 . .
O O7 0.47773(11) 0.52442(17) 0.33418(11) 0.0398(4) Uani d 1 . .
C C8 0.23389(15) 0.6311(2) 0.18562(15) 0.0283(4) Uani d 1 . .
H H8 0.2763 0.6121 0.2689 0.051(6) Uiso calc 1 . .
C C9 0.11929(16) 0.6956(2) 0.14281(18) 0.0364(5) Uani d 1 . .
H H9A 0.0941 0.7183 0.1991 0.047(6) Uiso calc 1 . .
H H9B 0.0930 0.7637 0.0785 0.061(8) Uiso calc 1 . .
C C10 0.12928(17) 0.5426(2) 0.11990(19) 0.0381(5) Uani d 1 . .
H H10A 0.1094 0.5152 0.0413 0.050(7) Uiso calc 1 . .
H H10B 0.1105 0.4698 0.1620 0.059(7) Uiso calc 1 . .
C C11 0.61644(14) 0.58208(18) 0.28108(13) 0.0216(4) Uani d 1 . .
C C12 0.70654(13) 0.65149(18) 0.37110(13) 0.0193(3) Uani d 1 . .
C C13 0.81286(13) 0.64965(18) 0.38042(13) 0.0203(3) Uani d 1 . .
H H13 0.8729 0.6992 0.4408 0.024(5) Uiso calc 1 . .
C C14 0.83109(14) 0.57524(18) 0.30129(13) 0.0206(3) Uani d 1 . .
C C15 0.74423(14) 0.50231(18) 0.21388(14) 0.0234(4) Uani d 1 . .
H H15 0.7574 0.4491 0.1610 0.035(5) Uiso calc 1 . .
C C16 0.63762(14) 0.50723(19) 0.20371(14) 0.0255(4) Uani d 1 . .
H H16 0.5778 0.4584 0.1426 0.031(5) Uiso calc 1 . .
S S17 0.69237(4) 0.74778(5) 0.47805(3) 0.02312(14) Uani d 1 . .
O O18 0.78878(12) 0.83833(16) 0.53321(11) 0.0387(4) Uani d 1 . .
C C19 0.94598(15) 0.5802(2) 0.31081(14) 0.0258(4) Uani d 1 . .
F F20 1.02531(9) 0.53642(16) 0.41237(10) 0.0490(4) Uani d 1 . .
O O21 0.58332(12) 0.81258(15) 0.42868(11) 0.0375(4) Uani d 1 . .
C C22 0.69982(18) 0.6145(2) 0.57370(15) 0.0336(4) Uani d 1 . .
H H22A 0.7714 0.5632 0.6026 0.048(7) Uiso calc 1 . .
H H22B 0.6378 0.5465 0.5351 0.057(7) Uiso calc 1 . .
H H22C 0.6945 0.6594 0.6370 0.046(6) Uiso calc 1 . .
F F23 0.95559(9) 0.49764(13) 0.23536(10) 0.0394(3) Uani d 1 . .
F F24 0.97390(10) 0.71318(13) 0.29720(12) 0.0467(3) 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_
_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
C5 O1 N2 . . 108.95(12) ?
C3 N2 O1 . . 104.84(13) ?
N2 C3 C4 . . 113.07(16) ?
N2 C3 H3 . . 123.5 ?
C4 C3 H3 . . 123.5 ?
C5 C4 C3 . . 103.41(14) ?
C5 C4 C6 . . 126.98(15) ?
C3 C4 C6 . . 129.59(15) ?
O1 C5 C4 . . 109.72(14) ?
O1 C5 C8 . . 116.89(15) ?
C4 C5 C8 . . 133.39(15) ?
O7 C6 C4 . . 123.08(16) ?
O7 C6 C11 . . 120.32(15) ?
C4 C6 C11 . . 116.57(13) ?
C5 C8 C9 . . 119.94(16) ?
C5 C8 C10 . . 118.40(16) ?
C9 C8 C10 . . 58.67(13) ?
C5 C8 H8 . . 115.9 ?
C9 C8 H8 . . 115.9 ?
C10 C8 H8 . . 115.9 ?
C10 C9 C8 . . 60.89(13) ?
C10 C9 H9A . . 117.7 ?
C8 C9 H9A . . 117.7 ?
C10 C9 H9B . . 117.7 ?
C8 C9 H9B . . 117.7 ?
H9A C9 H9B . . 114.8 ?
C9 C10 C8 . . 60.44(13) ?
C9 C10 H10A . . 117.7 ?
C8 C10 H10A . . 117.7 ?
C9 C10 H10B . . 117.7 ?
C8 C10 H10B . . 117.7 ?
H10A C10 H10B . . 114.8 ?
C16 C11 C12 . . 117.98(15) ?
C16 C11 C6 . . 118.53(15) ?
C12 C11 C6 . . 123.48(15) ?
C13 C12 C11 . . 120.91(14) ?
C13 C12 S17 . . 116.24(12) ?
C11 C12 S17 . . 122.85(12) ?
C14 C13 C12 . . 119.72(15) ?
C14 C13 H13 . . 120.1 ?
C12 C13 H13 . . 120.1 ?
C15 C14 C13 . . 120.32(15) ?
C15 C14 C19 . . 121.13(15) ?
C13 C14 C19 . . 118.51(15) ?
C14 C15 C16 . . 119.61(15) ?
C14 C15 H15 . . 120.2 ?
C16 C15 H15 . . 120.2 ?
C15 C16 C11 . . 121.41(15) ?
C15 C16 H16 . . 119.3 ?
C11 C16 H16 . . 119.3 ?
O18 S17 O21 . . 118.66(9) ?
O18 S17 C22 . . 108.52(10) ?
O21 S17 C22 . . 108.75(9) ?
O18 S17 C12 . . 106.83(8) ?
O21 S17 C12 . . 108.86(8) ?
C22 S17 C12 . . 104.27(9) ?
F23 C19 F24 . . 107.07(14) ?
F23 C19 F20 . . 106.22(14) ?
F24 C19 F20 . . 106.25(16) ?
F23 C19 C14 . . 113.20(15) ?
F24 C19 C14 . . 111.64(14) ?
F20 C19 C14 . . 112.02(13) ?
S17 C22 H22A . . 109.5 ?
S17 C22 H22B . . 109.5 ?
H22A C22 H22B . . 109.5 ?
S17 C22 H22C . . 109.5 ?
H22A C22 H22C . . 109.5 ?
H22B C22 H22C . . 109.5 ?
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
O1 C5 . 1.341(2) ?
O1 N2 . 1.4276(19) ?
N2 C3 . 1.292(2) ?
C3 C4 . 1.426(2) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.370(2) ?
C4 C6 . 1.458(2) ?
C5 C8 . 1.456(2) ?
C6 O7 . 1.215(2) ?
C6 C11 . 1.513(2) ?
C8 C9 . 1.501(3) ?
C8 C10 . 1.508(3) ?
C8 H8 . 1.0000 ?
C9 C10 . 1.474(3) ?
C9 H9A . 0.9900 ?
C9 H9B . 0.9900 ?
C10 H10A . 0.9900 ?
C10 H10B . 0.9900 ?
C11 C16 . 1.390(2) ?
C11 C12 . 1.400(2) ?
C12 C13 . 1.387(2) ?
C12 S17 . 1.7794(16) ?
C13 C14 . 1.386(2) ?
C13 H13 . 0.9500 ?
C14 C15 . 1.380(2) ?
C14 C19 . 1.503(2) ?
C15 C16 . 1.387(2) ?
C15 H15 . 0.9500 ?
C16 H16 . 0.9500 ?
S17 O18 . 1.4291(14) ?
S17 O21 . 1.4333(14) ?
S17 C22 . 1.7521(18) ?
C19 F23 . 1.326(2) ?
C19 F24 . 1.330(2) ?
C19 F20 . 1.335(2) ?
C22 H22A . 0.9800 ?
C22 H22B . 0.9800 ?
C22 H22C . 0.9800 ?
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
C16 H16 O21 2_645 0.95 2.35 3.214(2) 150.6
C10 H10A O18 2_645 0.99 2.63 3.355(2) 129.9
C3 H3 O21 4_575 0.95 2.71 3.522(2) 144.2

_cod_database_fobs_code 2244158
