#------------------------------------------------------------------------------
#$Date: 2023-07-12 10:48:10 +0300 (Wed, 12 Jul 2023) $
#$Revision: 285175 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/74/8107473.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_8107473
loop_
_publ_author_name
'Zhang, Jing'
'Zhang, Lixin'
_publ_section_title
;
 The crystal structure of
 2-(2-fluoro-4-methyl-5-((2,2,2-trifluoroethyl)thio)phenyl)isoindolin-1-one,
 C17H13F4NOS
;
_journal_issue                   3
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              479
_journal_page_last               481
_journal_paper_doi               10.1515/ncrs-2023-0042
_journal_volume                  238
_journal_year                    2023
_chemical_formula_moiety         'C17 H13 F4 N O S'
_chemical_formula_sum            'C17 H13 F4 N O S'
_chemical_formula_weight         355.34
_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
_atom_sites_solution_primary     dual
_cell_angle_alpha                83.116(8)
_cell_angle_beta                 80.305(9)
_cell_angle_gamma                73.204(9)
_cell_formula_units_Z            2
_cell_length_a                   6.1249(7)
_cell_length_b                   9.9306(10)
_cell_length_c                   13.1754(13)
_cell_measurement_reflns_used    1766
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      26.3280
_cell_measurement_theta_min      2.5560
_cell_volume                     754.08(14)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω    -56.00  36.00   1.00   10.00    --   11.90 -57.00-150.00   92
  2  ω    -16.00  74.00   1.00   10.00    --   11.90  77.00 120.00   90
  3  ω    -13.00  83.00   1.00   10.00    --   11.90  57.00   0.00   96
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0195139000
_diffrn_orient_matrix_UB_12      0.0491530000
_diffrn_orient_matrix_UB_13      -0.0434853000
_diffrn_orient_matrix_UB_21      0.0516296000
_diffrn_orient_matrix_UB_22      -0.0551452000
_diffrn_orient_matrix_UB_23      -0.0332944000
_diffrn_orient_matrix_UB_31      -0.1090061000
_diffrn_orient_matrix_UB_32      -0.0118841000
_diffrn_orient_matrix_UB_33      0.0006561000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0310
_diffrn_reflns_av_unetI/netI     0.0581
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4888
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         2.148
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.264
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72019
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.565
_exptl_crystal_description       needle
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.264
_refine_diff_density_min         -0.337
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         2652
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0666
_refine_ls_R_factor_gt           0.0460
_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)+(0.0420P)²+0.3188P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0968
_refine_ls_wR_factor_ref         0.1078
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2036
_reflns_number_total             2652
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_j_ncrs-2023-0042_suppl.cif
_cod_data_source_block           1
_cod_database_code               8107473
_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.
;
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C16(H16A,H16B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C10(H10), C13(H13)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;
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
S1 S 0.18420(12) 0.45943(8) 0.88482(6) 0.0299(2) Uani 1 1 d . . . . .
F1 F 1.0196(3) 0.50923(15) 0.60674(12) 0.0295(4) Uani 1 1 d . . . . .
F2 F 0.1815(3) 0.18028(19) 1.02542(13) 0.0454(5) Uani 1 1 d . . . . .
F3 F 0.1931(4) 0.05626(19) 0.90021(15) 0.0564(6) Uani 1 1 d . . . . .
F4 F 0.4719(3) 0.14536(17) 0.90564(13) 0.0410(4) Uani 1 1 d . . . . .
O1 O 1.2038(3) 0.21223(18) 0.61478(13) 0.0235(4) Uani 1 1 d . . . . .
N1 N 0.8326(3) 0.2969(2) 0.57365(15) 0.0181(5) Uani 1 1 d . . . . .
C1 C 0.8841(4) 0.1918(2) 0.42068(19) 0.0184(6) Uani 1 1 d . . . . .
C2 C 0.8680(5) 0.1430(3) 0.3288(2) 0.0236(6) Uani 1 1 d . . . . .
H2 H 0.728041 0.165367 0.303476 0.028 Uiso 1 1 calc R U . . .
C3 C 1.0672(5) 0.0595(3) 0.2756(2) 0.0259(6) Uani 1 1 d . . . . .
H3 H 1.059601 0.024370 0.214316 0.031 Uiso 1 1 calc R U . . .
C4 C 1.2765(5) 0.0280(3) 0.3122(2) 0.0256(6) Uani 1 1 d . . . . .
H4 H 1.408173 -0.026069 0.274375 0.031 Uiso 1 1 calc R U . . .
C5 C 1.2925(4) 0.0757(3) 0.4041(2) 0.0228(6) Uani 1 1 d . . . . .
H5 H 1.432562 0.053408 0.429404 0.027 Uiso 1 1 calc R U . . .
C6 C 1.0931(4) 0.1579(2) 0.45783(19) 0.0174(6) Uani 1 1 d . . . . .
C7 C 1.0608(4) 0.2224(2) 0.55712(19) 0.0189(6) Uani 1 1 d . . . . .
C8 C 0.7021(4) 0.2852(3) 0.49284(19) 0.0202(6) Uani 1 1 d . . . . .
H8A H 0.637340 0.376686 0.458536 0.024 Uiso 1 1 calc R U . . .
H8B H 0.579140 0.242068 0.520800 0.024 Uiso 1 1 calc R U . . .
C9 C 0.7342(4) 0.3878(2) 0.65465(19) 0.0182(6) Uani 1 1 d . . . . .
C10 C 0.5348(4) 0.3750(3) 0.71954(19) 0.0209(6) Uani 1 1 d . . . . .
H10 H 0.467375 0.305299 0.710621 0.025 Uiso 1 1 calc R U . . .
C11 C 0.4366(4) 0.4661(3) 0.7973(2) 0.0225(6) Uani 1 1 d . . . . .
C12 C 0.5317(5) 0.5750(3) 0.8103(2) 0.0233(6) Uani 1 1 d . . . . .
C13 C 0.7278(5) 0.5868(3) 0.7444(2) 0.0240(6) Uani 1 1 d . . . . .
H13 H 0.793895 0.658067 0.751200 0.029 Uiso 1 1 calc R U . . .
C14 C 0.8259(4) 0.4944(3) 0.6691(2) 0.0216(6) Uani 1 1 d . . . . .
C15 C 0.4248(5) 0.6771(3) 0.8931(2) 0.0316(7) Uani 1 1 d . . . . .
H15A H 0.265369 0.719900 0.886532 0.047 Uiso 1 1 calc R U . . .
H15B H 0.504101 0.748972 0.885453 0.047 Uiso 1 1 calc R U . . .
H15C H 0.437121 0.627302 0.959923 0.047 Uiso 1 1 calc R U . . .
C16 C 0.1204(5) 0.3001(3) 0.8621(2) 0.0306(7) Uani 1 1 d . . . . .
H16A H -0.044331 0.312885 0.878949 0.037 Uiso 1 1 calc R U . . .
H16B H 0.162634 0.284809 0.789203 0.037 Uiso 1 1 calc R U . . .
C17 C 0.2417(5) 0.1721(3) 0.9229(2) 0.0364(8) 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'
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_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
S1 C11 C12 C13 -179.7(2) . . . .
S1 C11 C12 C15 0.2(3) . . . .
S1 C16 C17 F2 62.6(3) . . . .
S1 C16 C17 F3 -178.03(19) . . . .
S1 C16 C17 F4 -58.1(3) . . . .
N1 C9 C10 C11 -178.7(2) . . . .
N1 C9 C14 F1 -2.5(4) . . . .
N1 C9 C14 C13 177.4(2) . . . .
C1 C2 C3 C4 -1.1(4) . . . .
C1 C6 C7 O1 177.4(2) . . . .
C1 C6 C7 N1 -1.9(3) . . . .
C2 C1 C6 C5 0.7(4) . . . .
C2 C1 C6 C7 -179.5(2) . . . .
C2 C1 C8 N1 -179.4(2) . . . .
C2 C3 C4 C5 1.6(4) . . . .
C3 C4 C5 C6 -1.0(4) . . . .
C4 C5 C6 C1 -0.2(4) . . . .
C4 C5 C6 C7 -179.9(2) . . . .
C5 C6 C7 O1 -2.8(4) . . . .
C5 C6 C7 N1 177.9(2) . . . .
C6 C1 C2 C3 0.0(4) . . . .
C6 C1 C8 N1 -0.8(3) . . . .
C7 N1 C8 C1 -0.5(3) . . . .
C7 N1 C9 C10 -129.5(3) . . . .
C7 N1 C9 C14 53.2(3) . . . .
C8 N1 C7 O1 -177.9(2) . . . .
C8 N1 C7 C6 1.4(3) . . . .
C8 N1 C9 C10 56.9(3) . . . .
C8 N1 C9 C14 -120.3(3) . . . .
C8 C1 C2 C3 178.5(2) . . . .
C8 C1 C6 C5 -178.1(2) . . . .
C8 C1 C6 C7 1.7(3) . . . .
C9 N1 C7 O1 8.0(4) . . . .
C9 N1 C7 C6 -172.6(2) . . . .
C9 N1 C8 C1 173.75(19) . . . .
C9 C10 C11 S1 -179.7(2) . . . .
C9 C10 C11 C12 1.9(4) . . . .
C10 C9 C14 F1 -179.8(2) . . . .
C10 C9 C14 C13 0.1(4) . . . .
C10 C11 C12 C13 -1.1(4) . . . .
C10 C11 C12 C15 178.8(3) . . . .
C11 S1 C16 C17 87.0(2) . . . .
C11 C12 C13 C14 -0.2(4) . . . .
C12 C13 C14 F1 -179.4(2) . . . .
C12 C13 C14 C9 0.7(4) . . . .
C14 C9 C10 C11 -1.3(4) . . . .
C15 C12 C13 C14 180.0(3) . . . .
C16 S1 C11 C10 8.3(3) . . . .
C16 S1 C11 C12 -173.1(2) . . . .
