#------------------------------------------------------------------------------
#$Date: 2023-06-15 12:27:43 +0300 (Thu, 15 Jun 2023) $
#$Revision: 284484 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/73/8107379.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_8107379
loop_
_publ_author_name
'Liu, Dongdong'
'Zhang, Lixin'
'Zhang, Jing'
_publ_section_title
;
 The crystal structure of methyl
 2-((4-chloro-2-fluoro-6-((2,2,2-trifluoroethyl)
 thio)phenoxy)methyl)benzoate, C17H13ClF4O3S
;
_journal_issue                   2
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              153
_journal_page_last               155
_journal_paper_doi               10.1515/ncrs-2022-0438
_journal_volume                  238
_journal_year                    2023
_chemical_formula_moiety         'C17 H13 Cl F4 O3 S'
_chemical_formula_sum            'C17 H13 Cl F4 O3 S'
_chemical_formula_weight         408.02
_chemical_name_systematic
;
methyl 2-((4-chloro-2-fluoro-6-((2,2,2-trifluoroethyl)thio)phe-noxy)methyl)
benzoate
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_primary     iterative
_cell_angle_alpha                90
_cell_angle_beta                 102.933(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.0097(10)
_cell_length_b                   4.4625(3)
_cell_length_c                   22.9520(19)
_cell_measurement_reflns_used    1115
_cell_measurement_temperature    120.00(10)
_cell_measurement_theta_max      71.0370
_cell_measurement_theta_min      2.8960
_cell_volume                     1698.0(2)
_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 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5-beta (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve 1.5-beta (Bourhis et al., 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.9997
_diffrn_measured_fraction_theta_max 0.9724
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω     47.00  74.00   1.00   10.00    --   40.73-123.00-138.00   27
  2  ω     25.00  94.00   1.00    5.00    --  106.95 -94.00-150.00   69
  3  ω     50.00 108.00   1.00    5.00    --  106.95 -94.00 -90.00   58
  4  ω     44.00 135.00   1.00    5.00    --  106.95 -30.00   0.00   91
  5  ω     90.00 128.00   1.00    5.00    --  106.95 -45.00 120.00   38
  6  ω     35.00  60.00   1.00    5.00    --  106.95 -45.00 120.00   25
  7  ω     32.00 178.00   1.00    5.00    --  106.95   0.00-150.00  146
  8  ω   -108.00 -16.00   1.00   10.00    --  -40.73 -38.00 -60.00   92
  9  ω   -115.00 -20.00   1.00   10.00    --  -40.73 -38.00-150.00   95
;
_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      0.0843623000
_diffrn_orient_matrix_UB_12      -0.0742985000
_diffrn_orient_matrix_UB_13      -0.0102016000
_diffrn_orient_matrix_UB_21      -0.0352160000
_diffrn_orient_matrix_UB_22      -0.0194980000
_diffrn_orient_matrix_UB_23      -0.0678337000
_diffrn_orient_matrix_UB_31      0.0166031000
_diffrn_orient_matrix_UB_32      0.3365526000
_diffrn_orient_matrix_UB_33      -0.0061138000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0595
_diffrn_reflns_av_unetI/netI     0.0865
_diffrn_reflns_Laue_measured_fraction_full 0.9997
_diffrn_reflns_Laue_measured_fraction_max 0.9724
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -3
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            5934
_diffrn_reflns_point_group_measured_fraction_full 0.9997
_diffrn_reflns_point_group_measured_fraction_max 0.9724
_diffrn_reflns_theta_full        67.6840
_diffrn_reflns_theta_max         73.61
_diffrn_reflns_theta_min         2.94
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.687
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.51283
_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    1.599
_exptl_crystal_description       needle
_exptl_crystal_F_000             838.052
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.5746
_refine_diff_density_min         -0.6618
_refine_diff_density_rms         0.1437
_refine_ls_d_res_high            0.8036
_refine_ls_d_res_low             15.0246
_refine_ls_goodness_of_fit_ref   1.0495
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    22
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3344
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0495
_refine_ls_R_factor_all          0.0932
_refine_ls_R_factor_gt           0.0606
_refine_ls_shift/su_max          -0.0004
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0593P)²+0.5274P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1344
_refine_ls_wR_factor_ref         0.1605
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              15
_reflns_limit_h_min              -20
_reflns_limit_k_max              5
_reflns_limit_k_min              0
_reflns_limit_l_max              28
_reflns_limit_l_min              -14
_reflns_number_gt                2294
_reflns_number_total             3344
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            suppl_j_ncrs-2022-0438_suppl.cif
_cod_data_source_block           exp_1115
_cod_original_sg_symbol_Hall     '-P 2ybc'
_cod_database_code               8107379
_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.
;
_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:
 C7(H7a,H7b), C14(H14a,H14b)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C10(H10), C12(H12)
2.c Idealised Me refined as rotating group:
 C17(H17a,H17b,H17c)
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x+1/2, -y+1/2, z+1/2'
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_refinement_flags_posn
Cl1 Cl 0.91695(6) -0.0121(3) 0.43916(5) 0.0341(3) Uani 1.000000 .
S1 S 0.59003(6) 0.0971(3) 0.42309(5) 0.0300(3) Uani 1.000000 .
F1 F 0.73286(15) 0.6325(6) 0.28602(11) 0.0372(6) Uani 1.000000 .
F2 F 0.70681(14) 0.1829(6) 0.54888(11) 0.0372(6) Uani 1.000000 .
F3 F 0.66108(17) -0.1928(7) 0.58997(12) 0.0483(8) Uani 1.000000 .
F4 F 0.58288(15) 0.1786(6) 0.55610(11) 0.0408(7) Uani 1.000000 .
O1 O 0.39193(17) 0.1786(7) 0.10544(12) 0.0303(7) Uani 1.000000 .
O2 O 0.50701(16) 0.0350(7) 0.16813(13) 0.0296(7) Uani 1.000000 .
O3 O 0.59929(16) 0.4843(6) 0.32799(12) 0.0296(7) Uani 1.000000 .
C1 C 0.4217(2) 0.3971(9) 0.20039(17) 0.0226(9) Uani 1.000000 .
C2 C 0.3452(2) 0.5258(9) 0.18629(19) 0.0273(9) Uani 1.000000 .
H2 H 0.3108(2) 0.4808(9) 0.14982(19) 0.0328(11) Uiso 1.000000 R
C3 C 0.3194(2) 0.7184(10) 0.22512(19) 0.0301(10) Uani 1.000000 .
H3 H 0.2684(2) 0.8050(10) 0.21482(19) 0.0361(12) Uiso 1.000000 R
C4 C 0.3706(2) 0.7805(10) 0.27968(19) 0.0314(10) Uani 1.000000 .
H4 H 0.3534(2) 0.9069(10) 0.30656(19) 0.0377(12) Uiso 1.000000 R
C5 C 0.4470(2) 0.6570(9) 0.29467(18) 0.0268(9) Uani 1.000000 .
H5 H 0.4806(2) 0.7011(9) 0.33155(18) 0.0321(11) Uiso 1.000000 R
C6 C 0.4741(2) 0.4682(9) 0.25539(18) 0.0238(9) Uani 1.000000 .
C7 C 0.5595(2) 0.3441(10) 0.27191(17) 0.0267(9) Uani 1.000000 .
H7a H 0.5881(2) 0.3903(10) 0.24090(17) 0.0320(11) Uiso 1.000000 R
H7b H 0.5583(2) 0.1282(10) 0.27655(17) 0.0320(11) Uiso 1.000000 R
C8 C 0.6739(2) 0.3610(9) 0.35242(18) 0.0260(9) Uani 1.000000 .
C9 C 0.7422(2) 0.4405(9) 0.33201(18) 0.0272(9) Uani 1.000000 .
C10 C 0.8170(2) 0.3264(10) 0.35724(19) 0.0288(9) Uani 1.000000 .
H10 H 0.8619(2) 0.3766(10) 0.34241(19) 0.0345(11) Uiso 1.000000 R
C11 C 0.8236(2) 0.1347(10) 0.40533(19) 0.0269(9) Uani 1.000000 .
C12 C 0.7576(2) 0.0567(10) 0.42828(18) 0.0271(9) Uani 1.000000 .
H12 H 0.7639(2) -0.0713(10) 0.46096(18) 0.0326(11) Uiso 1.000000 R
C13 C 0.6819(2) 0.1717(9) 0.40202(18) 0.0251(9) Uani 1.000000 .
C14 C 0.6182(3) -0.1521(10) 0.48547(19) 0.0324(10) Uani 1.000000 .
H14a H 0.5731(3) -0.2838(10) 0.48636(19) 0.0389(12) Uiso 1.000000 R
H14b H 0.6627(3) -0.2758(10) 0.47972(19) 0.0389(12) Uiso 1.000000 R
C15 C 0.6425(3) 0.0040(11) 0.5446(2) 0.0324(10) Uani 1.000000 .
C16 C 0.4463(2) 0.1851(10) 0.15794(18) 0.0261(9) Uani 1.000000 .
C17 C 0.4078(3) -0.0342(10) 0.06198(19) 0.0327(10) Uani 1.000000 .
H17a H 0.3668(10) -0.017(5) 0.0258(5) 0.0491(15) Uiso 1.000000 GR
H17b H 0.4596(8) 0.007(4) 0.0536(10) 0.0491(15) Uiso 1.000000 GR
H17c H 0.4075(18) -0.2336(11) 0.0776(6) 0.0491(15) Uiso 1.000000 GR
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0192 0.0096 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3684 0.6994 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0753 0.0550 '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'
O O 0.0523 0.0337 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3353 0.5513 '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
C14 S1 C13 104.0(2) . .
C17 O1 C16 115.8(3) . .
C8 O3 C7 113.0(3) . .
C6 C1 C2 119.1(4) . .
C16 C1 C2 119.8(4) . .
C16 C1 C6 121.1(3) . .
H2 C2 C1 119.2(2) . .
C3 C2 C1 121.6(4) . .
C3 C2 H2 119.2(2) . .
H3 C3 C2 120.6(2) . .
C4 C3 C2 118.9(4) . .
C4 C3 H3 120.6(3) . .
H4 C4 C3 119.6(3) . .
C5 C4 C3 120.8(4) . .
C5 C4 H4 119.6(3) . .
H5 C5 C4 119.6(3) . .
C6 C5 C4 120.8(4) . .
C6 C5 H5 119.6(2) . .
C5 C6 C1 118.9(4) . .
C7 C6 C1 121.3(4) . .
C7 C6 C5 119.8(4) . .
C6 C7 O3 107.1(3) . .
H7a C7 O3 110.3(2) . .
H7a C7 C6 110.3(2) . .
H7b C7 O3 110.3(2) . .
H7b C7 C6 110.3(2) . .
H7b C7 H7a 108.6 . .
C9 C8 O3 121.5(4) . .
C13 C8 O3 118.9(4) . .
C13 C8 C9 119.4(4) . .
C8 C9 F1 117.8(4) . .
C10 C9 F1 120.3(4) . .
C10 C9 C8 121.9(4) . .
H10 C10 C9 121.0(3) . .
C11 C10 C9 118.0(4) . .
C11 C10 H10 121.0(2) . .
C10 C11 Cl1 119.7(3) . .
C12 C11 Cl1 118.3(3) . .
C12 C11 C10 122.1(4) . .
H12 C12 C11 120.3(2) . .
C13 C12 C11 119.5(4) . .
C13 C12 H12 120.3(2) . .
C8 C13 S1 113.9(3) . .
C12 C13 S1 126.9(3) . .
C12 C13 C8 119.1(4) . .
H14a C14 S1 108.77(14) . .
H14b C14 S1 108.77(15) . .
H14b C14 H14a 107.7 . .
C15 C14 S1 113.9(3) . .
C15 C14 H14a 108.8(2) . .
C15 C14 H14b 108.8(2) . .
F3 C15 F2 106.7(3) . .
F4 C15 F2 106.2(4) . .
F4 C15 F3 106.4(4) . .
C14 C15 F2 113.5(4) . .
C14 C15 F3 111.5(4) . .
C14 C15 F4 112.1(3) . .
O2 C16 O1 123.2(4) . .
C1 C16 O1 111.3(3) . .
C1 C16 O2 125.5(4) . .
H17a C17 O1 109.5 . .
H17b C17 O1 109.5 . .
H17b C17 H17a 109.5 . .
H17c C17 O1 109.5 . .
H17c C17 H17a 109.5 . .
H17c C17 H17b 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 C11 1.733(4) .
S1 C13 1.767(4) .
S1 C14 1.791(5) .
F1 C9 1.341(4) .
F2 C15 1.340(5) .
F3 C15 1.344(5) .
F4 C15 1.351(5) .
O1 C16 1.345(5) .
O1 C17 1.446(5) .
O2 C16 1.209(5) .
O3 C7 1.455(4) .
O3 C8 1.382(5) .
C1 C2 1.391(5) .
C1 C6 1.409(5) .
C1 C16 1.484(6) .
C2 H2 0.9300 .
C2 C3 1.379(6) .
C3 H3 0.9300 .
C3 C4 1.384(6) .
C4 H4 0.9300 .
C4 C5 1.382(5) .
C5 H5 0.9300 .
C5 C6 1.387(5) .
C6 C7 1.520(5) .
C7 H7a 0.9700 .
C7 H7b 0.9700 .
C8 C9 1.393(6) .
C8 C13 1.400(6) .
C9 C10 1.372(6) .
C10 H10 0.9300 .
C10 C11 1.381(6) .
C11 C12 1.387(6) .
C12 H12 0.9300 .
C12 C13 1.392(5) .
C14 H14a 0.9700 .
C14 H14b 0.9700 .
C14 C15 1.500(6) .
C17 H17a 0.9600 .
C17 H17b 0.9600 .
C17 H17c 0.9600 .
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
Cl1 C11 C10 C9 -179.3(3) . . . .
Cl1 C11 C12 C13 179.9(3) . . . .
S1 C13 C8 O3 4.3(3) . . . .
S1 C13 C8 C9 179.0(3) . . . .
S1 C13 C12 C11 178.8(4) . . . .
S1 C14 C15 F2 -61.1(3) . . . .
S1 C14 C15 F3 178.4(3) . . . .
S1 C14 C15 F4 59.2(3) . . . .
F1 C9 C8 O3 -2.6(4) . . . .
F1 C9 C8 C13 -177.2(4) . . . .
F1 C9 C10 C11 178.6(4) . . . .
O1 C16 C1 C2 8.8(4) . . . .
O1 C16 C1 C6 -172.1(3) . . . .
O2 C16 C1 C2 -171.2(4) . . . .
O2 C16 C1 C6 8.0(5) . . . .
O3 C7 C6 C1 174.3(3) . . . .
O3 C7 C6 C5 -5.3(4) . . . .
O3 C8 C9 C10 177.9(4) . . . .
O3 C8 C13 C12 -177.4(4) . . . .
C1 C2 C3 C4 -1.0(5) . . . .
C1 C6 C5 C4 -1.8(5) . . . .
C2 C3 C4 C5 1.3(5) . . . .
C3 C4 C5 C6 0.1(5) . . . .
C4 C5 C6 C7 177.8(4) . . . .
C8 C9 C10 C11 -2.0(5) . . . .
C8 C13 C12 C11 0.8(5) . . . .
C9 C10 C11 C12 -0.1(5) . . . .
C10 C11 C12 C13 0.6(5) . . . .
