data_202012303
_audit_creation_date               2020-12-15
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number       '2014/7'
_audit_contact_author_address      ?
_audit_contact_author_email        ?
_audit_contact_author_name         ''
_audit_contact_author_phone        ?
_publ_contact_author_id_orcid      ?
_publ_section_references
;
Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H.
 (2009), J. Appl. Cryst. 42, 339-341.

Palatinus, L. & Chapuis, G. (2007). J. Appl. Cryst., 40, 786-790;
Palatinus, L. & van der Lee, A. (2008). J. Appl. Cryst. 41, 975-984;
Palatinus, L., Prathapa, S. J. & van Smaalen, S. (2012). J. Appl. Cryst. 45,
 575-580.

Sheldrick, G.M. (2015). Acta Cryst. C71, 3-8.
;
_chemical_name_common              ?
_chemical_name_systematic          ?
_chemical_formula_moiety           'C25 H25 F3 N2 O2 S'
_chemical_formula_sum              'C25 H25 F3 N2 O2 S'
_chemical_formula_weight           474.53
_chemical_melting_point            ?
_chemical_oxdiff_formula           C30H3O3N2S1
_chemical_oxdiff_usercomment       r
loop_
  _atom_type_symbol
  _atom_type_description
  _atom_type_scat_dispersion_real
  _atom_type_scat_dispersion_imag
  _atom_type_scat_source
 'C' 'C' 0.0181 0.0091 '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' 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'N' 'N' 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O' 'O' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'S' 'S' 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system        'monoclinic'
_space_group_IT_number             14
_space_group_name_H-M_alt          'P 1 21/c 1'
_space_group_name_Hall             '-P 2ybc'
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'

_cell_length_a                     24.1413(7)
_cell_length_b                     8.2624(2)
_cell_length_c                     12.0011(3)
_cell_angle_alpha                  90
_cell_angle_beta                   90.446(3)
_cell_angle_gamma                  90
_cell_volume                       2393.74(11)
_cell_formula_units_Z              4
_cell_measurement_reflns_used      2307
_cell_measurement_temperature      293(2)
_cell_measurement_theta_max        70.1840
_cell_measurement_theta_min        4.1380
_shelx_estimated_absorpt_T_max     0.895
_shelx_estimated_absorpt_T_min     0.717
_exptl_absorpt_coefficient_mu      1.618
_exptl_absorpt_correction_T_max    1.00000
_exptl_absorpt_correction_T_min    0.92598
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details     ?
_exptl_crystal_colour              colourless
_exptl_crystal_colour_lustre       .
_exptl_crystal_colour_primary      colourless
_exptl_crystal_density_diffrn      1.317
_exptl_crystal_density_meas        ?
_exptl_crystal_density_method      ?
_exptl_crystal_description         plate
_exptl_crystal_F_000               992
_exptl_crystal_size_max            0.22
_exptl_crystal_size_mid            0.1
_exptl_crystal_size_min            0.07
_exptl_transmission_factor_max     ?
_exptl_transmission_factor_min     ?
_diffrn_reflns_av_R_equivalents    0.0250
_diffrn_reflns_av_unetI/netI       0.0312
_diffrn_reflns_Laue_measured_fraction_full  0.999
_diffrn_reflns_Laue_measured_fraction_max  0.999
_diffrn_reflns_limit_h_max         28
_diffrn_reflns_limit_h_min         -28
_diffrn_reflns_limit_k_max         9
_diffrn_reflns_limit_k_min         -9
_diffrn_reflns_limit_l_max         12
_diffrn_reflns_limit_l_min         -14
_diffrn_reflns_number              9090
_diffrn_reflns_point_group_measured_fraction_full  0.999
_diffrn_reflns_point_group_measured_fraction_max  0.999
_diffrn_reflns_theta_full          67.071
_diffrn_reflns_theta_max           67.071
_diffrn_reflns_theta_min           3.662
_diffrn_ambient_temperature        293(2)
_diffrn_detector                   'CCD plate'
_diffrn_detector_area_resol_mean   16.2312
_diffrn_detector_type              Eos
_diffrn_measured_fraction_theta_full  0.999
_diffrn_measured_fraction_theta_max  0.999
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω      0.00  36.00   1.00    2.00    --  -33.50  77.00-120.00   36
  2  ω    -42.00 -17.00   1.00    2.00    --  -33.50 -57.00 120.00   25
  3  ω    -99.00 -61.00   1.00    2.00    --  -33.50 -57.00 120.00   38
  4  ω    -49.00 -23.00   1.00    2.00    --  -33.50  57.00 150.00   26
  5  ω    -52.00 -14.00   1.00    2.00    --  -33.50  77.00-120.00   38
  6  ω     81.00 107.00   1.00    2.00    --   36.47 178.00  60.00   26
  7  ω     57.00  98.00   1.00    2.00    --   36.47 178.00 120.00   41
  8  ω     62.00 108.00   1.00    2.00    --   36.47 178.00  30.00   46
  9  ω     31.00  56.00   1.00    2.00    --   36.47 -37.00 150.00   25
 10  ω     33.00  64.00   1.00    2.00    --   36.47 -77.00  90.00   31
 11  ω    -33.00  20.00   1.00    2.00    --   36.47 -77.00  90.00   53
 12  ω    -34.00  14.00   1.00    2.00    --   36.47 -37.00 150.00   48
 13  ω     96.00 175.00   1.00   10.50    --  108.00  30.00  30.00   79
 14  ω     77.00 106.00   1.00   10.50    --  108.00 -94.00 -30.00   29
 15  ω     99.00 176.00   1.00   10.50    --  108.00  77.00 120.00   77
 16  ω    114.00 174.00   1.00   10.50    --  108.00  61.00 -60.00   60
 17  ω     97.00 176.00   1.00   10.50    --  108.00  61.00  60.00   79
 18  ω     46.00  92.00   1.00   10.50    --  108.00 -94.00 -60.00   46
 19  ω     45.00 118.00   1.00   10.50    --  108.00 -45.00 -30.00   73
 20  ω     64.00  90.00   1.00   10.50    --  108.00-111.00  90.00   26
 21  ω     90.00 136.00   1.00   10.50    --  108.00  61.00-180.00   46
;
_diffrn_measurement_device         'four-circle diffractometer'
_diffrn_measurement_device_type    'Xcalibur, Eos, Gemini'
_diffrn_measurement_method         'ω scans'
_diffrn_orient_matrix_type        
 'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11        0.0004222000
_diffrn_orient_matrix_UB_12        0.1644654000
_diffrn_orient_matrix_UB_13        -0.0604482000
_diffrn_orient_matrix_UB_21        0.0625274000
_diffrn_orient_matrix_UB_22        0.0162229000
_diffrn_orient_matrix_UB_23        0.0238716000
_diffrn_orient_matrix_UB_31        0.0126534000
_diffrn_orient_matrix_UB_32        -0.0861657000
_diffrn_orient_matrix_UB_33        -0.1108123000
_diffrn_radiation_monochromator    graphite
_diffrn_radiation_probe            x-ray
_diffrn_radiation_type             CuK\a
_diffrn_radiation_wavelength       1.54184
_diffrn_source                     'fine-focus sealed X-ray tube'
_diffrn_source_type                'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage           0.000
_reflns_Friedel_fraction_full      .
_reflns_Friedel_fraction_max       .
_reflns_number_gt                  3165
_reflns_number_total               4276
_reflns_odcompleteness_completeness  99.93
_reflns_odcompleteness_iscentric   1
_reflns_odcompleteness_theta       66.97
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression       'I > 2σ(I)'
_computing_cell_refinement         'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection         'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction          'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics      'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material    'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement    'ShelXL (Sheldrick, 2015)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max           0.290
_refine_diff_density_min           -0.349
_refine_diff_density_rms           0.040
_refine_ls_extinction_coef         .
_refine_ls_extinction_method       none
_refine_ls_goodness_of_fit_ref     1.021
_refine_ls_hydrogen_treatment      constr
_refine_ls_matrix_type             full
_refine_ls_number_parameters       306
_refine_ls_number_reflns           4276
_refine_ls_number_restraints       54
_refine_ls_R_factor_all            0.0748
_refine_ls_R_factor_gt             0.0568
_refine_ls_restrained_S_all        1.053
_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)+(0.0904P)²+0.5497P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.1574
_refine_ls_wR_factor_ref           0.1757
_refine_special_details            ?
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C18-F1A
 1.4 with sigma of 0.02
 F3A-C18
 1.4 with sigma of 0.02
 C18-F2
 1.4 with sigma of 0.02
 C4-C5A
 1.55 with sigma of 0.02
 C22-C23
 1.42 with sigma of 0.02
 F2-F3 \\sim F2-F1 \\sim F3-F1 \\sim F2A-F1A \\sim F1A-F3A
 with sigma of 0.04
 C18-F2 \\sim C18-F3 \\sim C18-F1 \\sim C18-F2A \\sim C18-F1A \\sim C18-F3A
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(F2A) \\sim Ueq, Uanis(F2) \\sim Ueq, Uanis(F1) \\sim Ueq, Uanis(F1A)
\\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(F2) = Uanis(F2A)
Uanis(F1) = Uanis(F1A)
Uanis(F3) = Uanis(F3A)
Uanis(C10) = Uanis(C10A)
Uanis(C9) = Uanis(C9A)
Uanis(C8) = Uanis(C8A)
Uanis(C7) = Uanis(C7A)
Uanis(C6) = Uanis(C6A)
Uanis(C5) = Uanis(C5A)
4. Others
 Sof(F1A)=Sof(F2A)=Sof(F3A)=1-FVAR(1)
 Sof(F1)=Sof(F2)=Sof(F3)=FVAR(1)
 Sof(H4BC)=Sof(H4BD)=Sof(C5A)=Sof(C10A)=Sof(H10A)=Sof(C9A)=Sof(H9A)=Sof(C8A)=
 Sof(H8A)=Sof(C7A)=Sof(H7A)=Sof(C6A)=Sof(H6A)=1-FVAR(2)
 Sof(H4AA)=Sof(H4AB)=Sof(C5)=Sof(C10)=Sof(H10)=Sof(C9)=Sof(H9)=Sof(C8)=Sof(H8)=
 Sof(C7)=Sof(H7)=Sof(C6)=Sof(H6)=FVAR(2)
5.a Secondary CH2 refined with riding coordinates:
 C4(H4AA,H4AB), C4(H4BC,H4BD)
5.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C10(H10), C9(H9), C8(H8), C7(H7), C6(H6), C13(H13), C14(H14),
 C16(H16), C17(H17), C20(H20), C21(H21), C23(H23), C24(H24), C10A(H10A),
 C9A(H9A), C8A(H8A), C7A(H7A), C6A(H6A)
5.c Fitted hexagon refined as free rotating group:
 C5(C10,C9,C8,C7,C6), C5A(C10A,C9A,C8A,C7A,C6A)
5.d Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C), C11(H11A,H11B,H11C), C25(H25A,H25B,H25C)
;
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary       iterative
_atom_sites_solution_secondary     ?
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 0.20180(3) 0.81616(8) 0.55686(6) 0.0681(3) Uani 1 1 d . . . . .
 F1 F 0.45537(18) 0.9987(8) 0.2351(4) 0.162(2) Uani 0.796(6) 1 d D U P A 1
 F2 F 0.45608(19) 1.2518(6) 0.2243(5) 0.166(2) Uani 0.796(6) 1 d D U P A 1
 F3 F 0.41676(13) 1.1094(7) 0.0996(2) 0.1277(15) Uani 0.796(6) 1 d D . P A 1
 F1A F 0.4681(6) 1.113(3) 0.2704(14) 0.162(2) Uani 0.204(6) 1 d D U P A 2
 F2A F 0.4310(7) 1.2619(19) 0.1526(17) 0.166(2) Uani 0.204(6) 1 d D U P A 2
 F3A F 0.4255(6) 1.025(2) 0.1273(10) 0.1277(15) Uani 0.204(6) 1 d D . P A 2
 O1 O 0.18921(11) 0.9227(3) 0.64624(17) 0.0908(7) Uani 1 1 d . . . . .
 O2 O 0.18247(10) 0.6531(2) 0.5612(2) 0.0867(7) Uani 1 1 d . . . . .
 N1 N 0.17722(9) 0.8926(2) 0.44009(18) 0.0601(5) Uani 1 1 d . . . . .
 N2 N 0.22696(10) 1.1425(3) 0.46075(18) 0.0626(6) Uani 1 1 d . . . . .
 C1 C 0.17814(11) 1.0638(3) 0.4229(2) 0.0595(6) Uani 1 1 d . . . . .
 C2 C 0.13740(13) 1.1423(4) 0.3737(3) 0.0741(8) Uani 1 1 d . . . . .
 H2 H 0.1051 1.0850 0.3576 0.089 Uiso 1 1 calc R . . . .
 C3 C 0.13932(17) 1.3176(4) 0.3416(4) 0.1000(12) Uani 1 1 d . . . . .
 H3A H 0.1247 1.3306 0.2676 0.150 Uiso 1 1 calc GR . . . .
 H3B H 0.1770 1.3549 0.3440 0.150 Uiso 1 1 calc GR . . . .
 H3C H 0.1175 1.3796 0.3928 0.150 Uiso 1 1 calc GR . . . .
 C4 C 0.14838(12) 0.7883(3) 0.3584(2) 0.0678(7) Uani 1 1 d D . . . .
 H4AA H 0.1668 0.6839 0.3581 0.081 Uiso 0.736(4) 1 calc R . P B 1
 H4AB H 0.1531 0.8355 0.2851 0.081 Uiso 0.736(4) 1 calc R . P B 1
 H4BC H 0.1561 0.8285 0.2842 0.081 Uiso 0.264(4) 1 calc R . P B 2
 H4BD H 0.1637 0.6801 0.3638 0.081 Uiso 0.264(4) 1 calc R . P B 2
 C5 C 0.08629(12) 0.7591(5) 0.3758(3) 0.0694(8) Uani 0.736(4) 1 d . . P B 1
 C10 C 0.05838(14) 0.6705(5) 0.2945(3) 0.0938(14) Uani 0.736(4) 1 d G . P B 1
 H10 H 0.0771 0.6344 0.2318 0.113 Uiso 0.736(4) 1 calc R . P B 1
 C9 C 0.00243(15) 0.6357(6) 0.3068(4) 0.131(2) Uani 0.736(4) 1 d G . P B 1
 H9 H -0.0162 0.5764 0.2524 0.157 Uiso 0.736(4) 1 calc R . P B 1
 C8 C -0.02562(13) 0.6896(7) 0.4005(5) 0.128(3) Uani 0.736(4) 1 d G . P B 1
 H8 H -0.0631 0.6664 0.4088 0.154 Uiso 0.736(4) 1 calc R . P B 1
 C7 C 0.0023(2) 0.7783(6) 0.4818(4) 0.128(3) Uani 0.736(4) 1 d G . P B 1
 H7 H -0.0165 0.8144 0.5445 0.154 Uiso 0.736(4) 1 calc R . P B 1
 C6 C 0.0582(2) 0.8130(5) 0.4695(3) 0.100(2) Uani 0.736(4) 1 d G . P B 1
 H6 H 0.0769 0.8723 0.5238 0.120 Uiso 0.736(4) 1 calc R . P B 1
 C11 C 0.22194(17) 1.2575(4) 0.5537(3) 0.0886(10) Uani 1 1 d . . . . .
 H11A H 0.2261 1.3660 0.5263 0.133 Uiso 1 1 calc GR . . . .
 H11B H 0.2503 1.2357 0.6083 0.133 Uiso 1 1 calc GR . . . .
 H11C H 0.1862 1.2459 0.5873 0.133 Uiso 1 1 calc GR . . . .
 C12 C 0.27466(11) 1.1405(3) 0.3975(2) 0.0580(6) Uani 1 1 d . . . . .
 C13 C 0.27743(11) 1.0504(3) 0.2990(2) 0.0588(6) Uani 1 1 d . . . . .
 H13 H 0.2465 0.9931 0.2744 0.071 Uiso 1 1 calc R . . . .
 C14 C 0.32576(11) 1.0456(3) 0.2379(2) 0.0634(7) Uani 1 1 d . . . . .
 H14 H 0.3272 0.9844 0.1730 0.076 Uiso 1 1 calc R . . . .
 C15 C 0.37176(12) 1.1309(4) 0.2725(2) 0.0705(7) Uani 1 1 d . . . . .
 C16 C 0.36917(14) 1.2203(5) 0.3686(3) 0.0859(9) Uani 1 1 d . . . . .
 H16 H 0.4002 1.2779 0.3924 0.103 Uiso 1 1 calc R . . . .
 C17 C 0.32132(14) 1.2263(4) 0.4306(3) 0.0803(9) Uani 1 1 d . . . . .
 H17 H 0.3204 1.2884 0.4952 0.096 Uiso 1 1 calc R . . . .
 C18 C 0.42387(14) 1.1242(5) 0.2091(3) 0.0921(10) Uani 1 1 d D . . . .
 C19 C 0.27428(14) 0.8097(4) 0.5438(2) 0.0738(8) Uani 1 1 d . . . . .
 C20 C 0.29733(15) 0.7197(5) 0.4598(3) 0.0925(11) Uani 1 1 d . . . . .
 H20 H 0.2748 0.6622 0.4107 0.111 Uiso 1 1 calc R . . . .
 C21 C 0.35452(19) 0.7148(7) 0.4487(4) 0.1154(15) Uani 1 1 d . . . . .
 H21 H 0.3699 0.6540 0.3915 0.139 Uiso 1 1 calc R . . . .
 C22 C 0.3887(2) 0.7978(8) 0.5202(6) 0.1285(19) Uani 1 1 d D . . . .
 C23 C 0.3654(2) 0.8828(7) 0.6044(5) 0.133(2) Uani 1 1 d D . . . .
 H23 H 0.3883 0.9366 0.6548 0.159 Uiso 1 1 calc R . . . .
 C24 C 0.3084(2) 0.8921(5) 0.6180(4) 0.1060(12) Uani 1 1 d . . . . .
 H24 H 0.2934 0.9524 0.6758 0.127 Uiso 1 1 calc R . . . .
 C25 C 0.4511(2) 0.7938(10) 0.5051(7) 0.193(4) Uani 1 1 d . . . . .
 H25A H 0.4621 0.6881 0.4806 0.290 Uiso 1 1 calc GR . . . .
 H25B H 0.4690 0.8182 0.5748 0.290 Uiso 1 1 calc GR . . . .
 H25C H 0.4616 0.8727 0.4505 0.290 Uiso 1 1 calc GR . . . .
 C5A C 0.0890(3) 0.7779(15) 0.3714(10) 0.0694(8) Uani 0.264(4) 1 d D . P B 2
 C10A C 0.0573(4) 0.8239(16) 0.2794(8) 0.0938(14) Uani 0.264(4) 1 d G . P B 2
 H10A H 0.0746 0.8596 0.2149 0.113 Uiso 0.264(4) 1 calc R . P B 2
 C9A C -0.0001(4) 0.8166(19) 0.2839(11) 0.131(2) Uani 0.264(4) 1 d G . P B 2
 H9A H -0.0213 0.8474 0.2224 0.157 Uiso 0.264(4) 1 calc R . P B 2
 C8A C -0.0260(4) 0.763(2) 0.3802(14) 0.128(3) Uani 0.264(4) 1 d G . P B 2
 H8A H -0.0644 0.7583 0.3832 0.154 Uiso 0.264(4) 1 calc R . P B 2
 C7A C 0.0057(6) 0.717(2) 0.4722(11) 0.128(3) Uani 0.264(4) 1 d G . P B 2
 H7A H -0.0116 0.6815 0.5367 0.154 Uiso 0.264(4) 1 calc R . P B 2
 C6A C 0.0631(6) 0.7245(16) 0.4677(9) 0.100(2) Uani 0.264(4) 1 d G . P B 2
 H6A H 0.0843 0.6937 0.5292 0.120 Uiso 0.264(4) 1 calc R . P B 2


_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
  _geom_bond_atom_site_label_1
  _geom_bond_atom_site_label_2
  _geom_bond_distance
  _geom_bond_site_symmetry_2
  _geom_bond_publ_flag
 S1 O1 1.422(2) . ?
 S1 O2 1.427(2) . ?
 S1 N1 1.644(2) . ?
 S1 C19 1.759(3) . ?
 F1 C18 1.322(5) . ?
 F2 C18 1.322(5) . ?
 F3 C18 1.329(5) . ?
 F1A C18 1.295(10) . ?
 F2A C18 1.336(13) . ?
 F3A C18 1.280(11) . ?
 N1 C1 1.430(3) . ?
 N1 C4 1.476(4) . ?
 N2 C1 1.417(4) . ?
 N2 C11 1.472(3) . ?
 N2 C12 1.384(3) . ?
 C1 C2 1.314(4) . ?
 C2 H2 0.9300 . ?
 C2 C3 1.500(4) . ?
 C3 H3A 0.9600 . ?
 C3 H3B 0.9600 . ?
 C3 H3C 0.9600 . ?
 C4 H4AA 0.9700 . ?
 C4 H4AB 0.9700 . ?
 C4 H4BC 0.9700 . ?
 C4 H4BD 0.9700 . ?
 C4 C5 1.534(4) . ?
 C4 C5A 1.447(9) . ?
 C5 C10 1.3900 . ?
 C5 C6 1.3900 . ?
 C10 H10 0.9300 . ?
 C10 C9 1.3900 . ?
 C9 H9 0.9300 . ?
 C9 C8 1.3900 . ?
 C8 H8 0.9300 . ?
 C8 C7 1.3900 . ?
 C7 H7 0.9300 . ?
 C7 C6 1.3900 . ?
 C6 H6 0.9300 . ?
 C11 H11A 0.9600 . ?
 C11 H11B 0.9600 . ?
 C11 H11C 0.9600 . ?
 C12 C13 1.400(4) . ?
 C12 C17 1.386(4) . ?
 C13 H13 0.9300 . ?
 C13 C14 1.383(4) . ?
 C14 H14 0.9300 . ?
 C14 C15 1.377(4) . ?
 C15 C16 1.372(5) . ?
 C15 C18 1.477(4) . ?
 C16 H16 0.9300 . ?
 C16 C17 1.380(5) . ?
 C17 H17 0.9300 . ?
 C19 C20 1.374(5) . ?
 C19 C24 1.387(5) . ?
 C20 H20 0.9300 . ?
 C20 C21 1.389(5) . ?
 C21 H21 0.9300 . ?
 C21 C22 1.370(8) . ?
 C22 C23 1.358(7) . ?
 C22 C25 1.518(7) . ?
 C23 H23 0.9300 . ?
 C23 C24 1.389(7) . ?
 C24 H24 0.9300 . ?
 C25 H25A 0.9600 . ?
 C25 H25B 0.9600 . ?
 C25 H25C 0.9600 . ?
 C5A C10A 1.3900 . ?
 C5A C6A 1.3900 . ?
 C10A H10A 0.9300 . ?
 C10A C9A 1.3900 . ?
 C9A H9A 0.9300 . ?
 C9A C8A 1.3900 . ?
 C8A H8A 0.9300 . ?
 C8A C7A 1.3900 . ?
 C7A H7A 0.9300 . ?
 C7A C6A 1.3900 . ?
 C6A H6A 0.9300 . ?

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
  _geom_angle_publ_flag
 O1 S1 O2 119.03(14) . . ?
 O1 S1 N1 109.09(13) . . ?
 O1 S1 C19 107.75(16) . . ?
 O2 S1 N1 106.13(14) . . ?
 O2 S1 C19 107.47(15) . . ?
 N1 S1 C19 106.76(12) . . ?
 C1 N1 S1 119.83(19) . . ?
 C1 N1 C4 119.3(2) . . ?
 C4 N1 S1 120.45(18) . . ?
 C1 N2 C11 117.8(2) . . ?
 C12 N2 C1 120.8(2) . . ?
 C12 N2 C11 119.8(2) . . ?
 N2 C1 N1 114.9(2) . . ?
 C2 C1 N1 122.7(3) . . ?
 C2 C1 N2 122.4(3) . . ?
 C1 C2 H2 117.7 . . ?
 C1 C2 C3 124.5(3) . . ?
 C3 C2 H2 117.7 . . ?
 C2 C3 H3A 109.5 . . ?
 C2 C3 H3B 109.5 . . ?
 C2 C3 H3C 109.5 . . ?
 H3A C3 H3B 109.5 . . ?
 H3A C3 H3C 109.5 . . ?
 H3B C3 H3C 109.5 . . ?
 N1 C4 H4AA 108.0 . . ?
 N1 C4 H4AB 108.0 . . ?
 N1 C4 H4BC 108.5 . . ?
 N1 C4 H4BD 108.5 . . ?
 N1 C4 C5 117.3(2) . . ?
 H4AA C4 H4AB 107.2 . . ?
 H4BC C4 H4BD 107.5 . . ?
 C5 C4 H4AA 108.0 . . ?
 C5 C4 H4AB 108.0 . . ?
 C5A C4 N1 115.3(5) . . ?
 C5A C4 H4BC 108.5 . . ?
 C5A C4 H4BD 108.5 . . ?
 C10 C5 C4 117.1(3) . . ?
 C10 C5 C6 120.0 . . ?
 C6 C5 C4 122.8(3) . . ?
 C5 C10 H10 120.0 . . ?
 C9 C10 C5 120.0 . . ?
 C9 C10 H10 120.0 . . ?
 C10 C9 H9 120.0 . . ?
 C10 C9 C8 120.0 . . ?
 C8 C9 H9 120.0 . . ?
 C9 C8 H8 120.0 . . ?
 C9 C8 C7 120.0 . . ?
 C7 C8 H8 120.0 . . ?
 C8 C7 H7 120.0 . . ?
 C6 C7 C8 120.0 . . ?
 C6 C7 H7 120.0 . . ?
 C5 C6 H6 120.0 . . ?
 C7 C6 C5 120.0 . . ?
 C7 C6 H6 120.0 . . ?
 N2 C11 H11A 109.5 . . ?
 N2 C11 H11B 109.5 . . ?
 N2 C11 H11C 109.5 . . ?
 H11A C11 H11B 109.5 . . ?
 H11A C11 H11C 109.5 . . ?
 H11B C11 H11C 109.5 . . ?
 N2 C12 C13 121.0(2) . . ?
 N2 C12 C17 121.0(2) . . ?
 C17 C12 C13 118.0(3) . . ?
 C12 C13 H13 119.7 . . ?
 C14 C13 C12 120.6(3) . . ?
 C14 C13 H13 119.7 . . ?
 C13 C14 H14 119.7 . . ?
 C15 C14 C13 120.5(3) . . ?
 C15 C14 H14 119.7 . . ?
 C14 C15 C18 120.9(3) . . ?
 C16 C15 C14 119.2(3) . . ?
 C16 C15 C18 119.9(3) . . ?
 C15 C16 H16 119.5 . . ?
 C15 C16 C17 121.1(3) . . ?
 C17 C16 H16 119.5 . . ?
 C12 C17 H17 119.7 . . ?
 C16 C17 C12 120.6(3) . . ?
 C16 C17 H17 119.7 . . ?
 F1 C18 F3 103.4(4) . . ?
 F1 C18 C15 113.5(3) . . ?
 F2 C18 F1 104.9(4) . . ?
 F2 C18 F3 106.3(4) . . ?
 F2 C18 C15 113.7(4) . . ?
 F3 C18 C15 114.1(3) . . ?
 F1A C18 F2A 103.8(12) . . ?
 F1A C18 C15 114.3(9) . . ?
 F2A C18 C15 110.1(8) . . ?
 F3A C18 F1A 111.1(11) . . ?
 F3A C18 F2A 98.8(11) . . ?
 F3A C18 C15 116.8(7) . . ?
 C20 C19 S1 119.4(3) . . ?
 C20 C19 C24 119.7(4) . . ?
 C24 C19 S1 120.9(3) . . ?
 C19 C20 H20 120.2 . . ?
 C19 C20 C21 119.7(4) . . ?
 C21 C20 H20 120.2 . . ?
 C20 C21 H21 119.3 . . ?
 C22 C21 C20 121.4(5) . . ?
 C22 C21 H21 119.3 . . ?
 C21 C22 C25 120.5(7) . . ?
 C23 C22 C21 118.2(5) . . ?
 C23 C22 C25 121.2(7) . . ?
 C22 C23 H23 118.9 . . ?
 C22 C23 C24 122.3(5) . . ?
 C24 C23 H23 118.9 . . ?
 C19 C24 C23 118.7(5) . . ?
 C19 C24 H24 120.6 . . ?
 C23 C24 H24 120.6 . . ?
 C22 C25 H25A 109.5 . . ?
 C22 C25 H25B 109.5 . . ?
 C22 C25 H25C 109.5 . . ?
 H25A C25 H25B 109.5 . . ?
 H25A C25 H25C 109.5 . . ?
 H25B C25 H25C 109.5 . . ?
 C10A C5A C4 116.0(8) . . ?
 C10A C5A C6A 120.0 . . ?
 C6A C5A C4 124.0(8) . . ?
 C5A C10A H10A 120.0 . . ?
 C5A C10A C9A 120.0 . . ?
 C9A C10A H10A 120.0 . . ?
 C10A C9A H9A 120.0 . . ?
 C10A C9A C8A 120.0 . . ?
 C8A C9A H9A 120.0 . . ?
 C9A C8A H8A 120.0 . . ?
 C7A C8A C9A 120.0 . . ?
 C7A C8A H8A 120.0 . . ?
 C8A C7A H7A 120.0 . . ?
 C8A C7A C6A 120.0 . . ?
 C6A C7A H7A 120.0 . . ?
 C5A C6A H6A 120.0 . . ?
 C7A C6A C5A 120.0 . . ?
 C7A C6A H6A 120.0 . . ?

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
  _geom_torsion_publ_flag
 S1 N1 C1 N2 40.3(3) . . . . ?
 S1 N1 C1 C2 -141.1(2) . . . . ?
 S1 N1 C4 C5 85.4(3) . . . . ?
 S1 N1 C4 C5A 91.5(6) . . . . ?
 S1 C19 C20 C21 179.6(3) . . . . ?
 S1 C19 C24 C23 179.8(3) . . . . ?
 O1 S1 N1 C1 36.1(2) . . . . ?
 O1 S1 N1 C4 -136.8(2) . . . . ?
 O1 S1 C19 C20 -177.4(3) . . . . ?
 O1 S1 C19 C24 3.6(3) . . . . ?
 O2 S1 N1 C1 165.46(19) . . . . ?
 O2 S1 N1 C4 -7.4(2) . . . . ?
 O2 S1 C19 C20 53.2(3) . . . . ?
 O2 S1 C19 C24 -125.8(3) . . . . ?
 N1 S1 C19 C20 -60.3(3) . . . . ?
 N1 S1 C19 C24 120.7(3) . . . . ?
 N1 C1 C2 C3 -172.4(3) . . . . ?
 N1 C4 C5 C10 175.5(3) . . . . ?
 N1 C4 C5 C6 -6.4(4) . . . . ?
 N1 C4 C5A C10A 122.2(7) . . . . ?
 N1 C4 C5A C6A -58.3(10) . . . . ?
 N2 C1 C2 C3 6.2(5) . . . . ?
 N2 C12 C13 C14 -178.3(2) . . . . ?
 N2 C12 C17 C16 178.3(3) . . . . ?
 C1 N1 C4 C5 -87.6(3) . . . . ?
 C1 N1 C4 C5A -81.4(6) . . . . ?
 C1 N2 C12 C13 -5.2(4) . . . . ?
 C1 N2 C12 C17 175.6(3) . . . . ?
 C4 N1 C1 N2 -146.7(2) . . . . ?
 C4 N1 C1 C2 31.9(4) . . . . ?
 C4 C5 C10 C9 178.1(3) . . . . ?
 C4 C5 C6 C7 -178.0(4) . . . . ?
 C4 C5A C10A C9A 179.5(11) . . . . ?
 C4 C5A C6A C7A -179.4(12) . . . . ?
 C5 C10 C9 C8 0.0 . . . . ?
 C10 C5 C6 C7 0.0 . . . . ?
 C10 C9 C8 C7 0.0 . . . . ?
 C9 C8 C7 C6 0.0 . . . . ?
 C8 C7 C6 C5 0.0 . . . . ?
 C6 C5 C10 C9 0.0 . . . . ?
 C11 N2 C1 N1 -114.4(3) . . . . ?
 C11 N2 C1 C2 66.9(4) . . . . ?
 C11 N2 C12 C13 -170.3(3) . . . . ?
 C11 N2 C12 C17 10.4(4) . . . . ?
 C12 N2 C1 N1 80.1(3) . . . . ?
 C12 N2 C1 C2 -98.6(3) . . . . ?
 C12 C13 C14 C15 -0.7(4) . . . . ?
 C13 C12 C17 C16 -0.9(5) . . . . ?
 C13 C14 C15 C16 0.2(5) . . . . ?
 C13 C14 C15 C18 178.8(3) . . . . ?
 C14 C15 C16 C17 -0.2(5) . . . . ?
 C14 C15 C18 F1 -84.6(5) . . . . ?
 C14 C15 C18 F2 155.7(4) . . . . ?
 C14 C15 C18 F3 33.5(6) . . . . ?
 C14 C15 C18 F1A -138.3(13) . . . . ?
 C14 C15 C18 F2A 105.4(11) . . . . ?
 C14 C15 C18 F3A -6.1(10) . . . . ?
 C15 C16 C17 C12 0.6(6) . . . . ?
 C16 C15 C18 F1 94.0(5) . . . . ?
 C16 C15 C18 F2 -25.7(6) . . . . ?
 C16 C15 C18 F3 -147.9(4) . . . . ?
 C16 C15 C18 F1A 40.3(14) . . . . ?
 C16 C15 C18 F2A -76.0(11) . . . . ?
 C16 C15 C18 F3A 172.4(9) . . . . ?
 C17 C12 C13 C14 1.0(4) . . . . ?
 C18 C15 C16 C17 -178.8(3) . . . . ?
 C19 S1 N1 C1 -80.1(2) . . . . ?
 C19 S1 N1 C4 107.0(2) . . . . ?
 C19 C20 C21 C22 0.2(6) . . . . ?
 C20 C19 C24 C23 0.8(5) . . . . ?
 C20 C21 C22 C23 1.5(7) . . . . ?
 C20 C21 C22 C25 -178.7(4) . . . . ?
 C21 C22 C23 C24 -2.1(8) . . . . ?
 C22 C23 C24 C19 1.0(7) . . . . ?
 C24 C19 C20 C21 -1.4(5) . . . . ?
 C25 C22 C23 C24 178.1(4) . . . . ?
 C5A C10A C9A C8A 0.0 . . . . ?
 C10A C5A C6A C7A 0.0 . . . . ?
 C10A C9A C8A C7A 0.0 . . . . ?
 C9A C8A C7A C6A 0.0 . . . . ?
 C8A C7A C6A C5A 0.0 . . . . ?
 C6A C5A C10A C9A 0.0 . . . . ?

_olex2_submission_special_instructions  'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max  1.222
_oxdiff_exptl_absorpt_empirical_full_min  0.880
