# Supplementary Information (SI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_35
_database_code_depnum_ccdc_archive 'CCDC 2410987'
loop_
_audit_author_name
_audit_author_address
'Aidan McKay'
;University of St Andews
United Kingdom
;
_audit_update_record             
;
2024-12-17 deposited with the CCDC.	2025-04-30 downloaded from the CCDC.
;
_audit_creation_date             2024-07-08
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        
'(R,Z)-4-((3-(4-cyanophenyl)-4-oxo-6-(trifluoromethyl)-1,3-thiazinan-2-ylidene)amino)benzonitrile chloroform solvate'
_chemical_formula_moiety         'C19 H11 F3 N4 O S, 0.333(C H Cl3)'
_chemical_formula_sum            'C19.33 H11.33 Cl F3 N4 O S'
_chemical_formula_weight         440.17
_chemical_absolute_configuration ad
_chemical_melting_point          ?
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'
Cl Cl 0.3639 0.7018 '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      trigonal
_space_group_IT_number           146
_space_group_name_H-M_alt        'R 3'
_space_group_name_Hall           'R 3'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'

_cell_length_a                   21.67271(16)
_cell_length_b                   21.67271(16)
_cell_length_c                   10.76754(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     4379.99(8)
_cell_formula_units_Z            9
_cell_measurement_reflns_used    36400
_cell_measurement_temperature    173
_cell_measurement_theta_max      66.0750
_cell_measurement_theta_min      4.0730
_shelx_estimated_absorpt_T_max   0.599
_shelx_estimated_absorpt_T_min   0.449
_exptl_absorpt_coefficient_mu    3.174
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83024
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.82a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.502
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             2010
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0239
_diffrn_reflns_av_unetI/netI     0.0090
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            41954
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        66.587
_diffrn_reflns_theta_max         66.587
_diffrn_reflns_theta_min         4.080
_diffrn_ambient_temperature      173
_diffrn_detector                 'hybrid photon counting detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Dectris PILATUS P100K'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -83.00   4.00   1.00    1.00    --    0.00 -37.00 -30.00   87
  2  ω    -83.00 -12.00   1.00    1.00    --    0.00 -19.00  30.00   71
  3  ω    -23.00  47.00   1.00    1.00    --    0.00 -82.00-150.00   70
  4  ω    -20.00  35.00   1.00    1.00    --    0.00  77.00-150.00   55
  5  ω     12.00  89.00   1.00    1.00    --    0.00  19.00  90.00   77
  6  ω    -33.00  48.00   1.00    1.00    --    5.00 -77.00  60.00   81
  7  ω    -15.00  35.00   1.00    1.00    --    5.00  77.00  30.00   50
  8  ω    -78.00  -7.00   1.00    1.00    --    5.00 -19.00 150.00   71
  9  ω    -15.00  35.00   1.00    1.00    --    5.00  77.00 -30.00   50
 10  ω    -15.00  35.00   1.00    1.00    --    5.00  77.00 150.00   50
 11  ω   -141.00 -25.00   1.00    1.00    --  -57.40 -57.00  60.00  116
 12  ω   -141.00 -25.00   1.00    1.00    --  -57.40 -57.00 -60.00  116
 13  ω    -60.00  32.00   1.00    1.00    --  -57.40  37.00  60.00   92
 14  ω   -141.00 -25.00   1.00    1.00    --  -57.40 -57.00 150.00  116
 15  ω   -141.00 -25.00   1.00    1.00    --  -57.40 -57.00-120.00  116
 16  ω    -78.00  32.00   1.00    1.00    --  -57.40  77.00 -60.00  110
 17  ω    -70.00  32.00   1.00    1.00    --  -57.40  57.00 -90.00  102
 18  ω   -141.00 -25.00   1.00    1.00    --  -57.40 -57.00 120.00  116
 19  ω   -141.00 -25.00   1.00    1.00    --  -57.40 -57.00   0.00  116
 20  ω   -141.00 -25.00   1.00    1.00    --  -57.40 -57.00-150.00  116
 21  ω    -78.00  32.00   1.00    1.00    --  -57.40  77.00  90.00  110
 22  ω   -167.00 -47.00   1.00    1.00    --  -83.30 -67.00 -52.00  120
 23  ω   -167.00 -45.00   1.00    1.00    --  -83.30 -70.00 -80.55  122
 24  ω   -167.00 -51.00   1.00    1.00    --  -83.30 -57.00 -30.00  116
 25  ω   -167.00 -51.00   1.00    1.00    --  -83.30 -57.00  90.00  116
 26  ω   -167.00 -45.00   1.00    1.00    --  -83.30 -71.00-166.62  122
 27  ω   -167.00 -51.00   1.00    1.00    --  -83.30 -57.00-120.00  116
 28  ω   -167.00 -51.00   1.00    1.00    --  -83.30 -57.00-150.00  116
 29  ω   -167.00 -47.00   1.00    1.00    --  -83.30 -67.00-164.64  120
 30  ω   -167.00 -46.00   1.00    1.00    --  -83.30 -69.00 142.99  121
 31  ω    -84.00 -51.00   1.00    1.00    --  -83.30 -57.00  30.00   33
 32  ω    -72.00 -45.00   1.00    1.00    --  -83.30 -71.00 156.08   27
 33  ω    -73.00 -48.00   1.00    1.00    --  -83.30 -66.00 -29.70   25
 34  ω   -100.00 -36.00   1.00    1.00    --  -83.30  77.00-150.00   64
 35  ω    -79.00 -50.00   1.00    1.00    --  -83.30 -62.00   6.16   29
 36  ω    -84.00 -51.00   1.00    1.00    --  -83.30 -57.00  60.00   33
 37  ω   -133.00-106.00   1.00    1.00    -- -109.20 -73.00  35.03   27
 38  ω   -183.00-157.00   1.00    1.00    -- -109.20 -73.00  35.03   26
 39  ω   -192.00-128.00   1.00    1.00    -- -109.20 -64.00 -13.52   64
 40  ω   -131.00 -73.00   1.00    1.00    -- -109.20 -72.00 151.34   58
 41  ω    -98.00 -71.00   1.00    1.00    -- -109.20 -71.00 -58.83   27
 42  ω   -191.00-165.00   1.00    1.00    -- -109.20 -72.00 151.34   26
 43  ω    -97.00 -71.00   1.00    1.00    -- -109.20 -71.00 159.13   26
 44  ω   -165.00-139.00   1.00    1.00    -- -109.20 -37.00  90.00   26
 45  ω    -97.00 -21.00   1.00    1.00    -- -109.20  80.00-138.51   76
 46  ω   -145.00-112.00   1.00    1.00    -- -109.20 -37.00 -90.00   33
 47  ω    -99.00 -73.00   1.00    1.00    -- -109.20  77.00 -90.00   26
 48  ω   -191.00-130.00   1.00    1.00    -- -109.20 -71.00 -58.83   61
 49  ω    -90.00 -64.00   1.00    1.00    -- -109.20   3.00 168.55   26
 50  ω   -107.00 -79.00   1.00    1.00    -- -109.20 -56.00 177.08   28
 51  ω   -124.00 -77.00   1.00    1.00    -- -109.20 -58.00   0.59   47
 52  ω    -95.00 -50.00   1.00    1.00    -- -109.20  82.00-109.29   45
 53  ω    -46.00 -20.00   1.00    1.00    -- -109.20  82.00-109.29   26
 54  ω    -94.00 -69.00   1.00    1.00    -- -109.20 -73.00-129.37   25
 55  ω    -96.00 -63.00   1.00    1.00    -- -109.20  77.00 120.00   33
 56  ω   -187.00-162.00   1.00    1.00    -- -109.20 -71.00 159.13   25
 57  ω    -97.00 -42.00   1.00    1.00    -- -109.20  82.00 155.28   55
 58  ω   -160.00-124.00   1.00    1.00    -- -109.20 -16.00 -69.81   36
 59  ω   -138.00-112.00   1.00    1.00    -- -109.20 -73.00-129.37   26
 60  ω   -136.00 -77.00   1.00    1.00    -- -109.20 -59.00 114.13   59
 61  ω   -131.00 -82.00   1.00    1.00    -- -109.20 -59.00 -23.89   49
 62  ω    -98.00 -72.00   1.00    1.00    -- -109.20 -69.00-169.59   26
 63  ω    -94.00 -69.00   1.00    1.00    -- -109.20 -73.00-101.47   25
 64  ω   -147.00-121.00   1.00    1.00    -- -109.20 -72.00  41.47   26
 65  ω    -97.00 -22.00   1.00    1.00    -- -109.20  19.00  30.00   75
 66  ω   -154.00-128.00   1.00    1.00    -- -109.20 -69.00-169.59   26
 67  ω   -176.00-151.00   1.00    1.00    -- -109.20 -62.00 -79.18   25
 68  ω   -138.00 -76.00   1.00    1.00    -- -109.20 -61.00 -35.08   62
 69  ω   -188.00-162.00   1.00    1.00    -- -109.20 -69.00-169.59   26
 70  ω   -172.00-127.00   1.00    1.00    -- -109.20 -73.00-101.47   45
 71  ω   -100.00 -64.00   1.00    1.00    -- -109.20  77.00 -30.00   36
 72  ω   -107.00 -76.00   1.00    1.00    -- -109.20 -72.00-144.12   31
 73  ω    -97.00 -70.00   1.00    1.00    -- -109.20 -72.00  78.25   27
 74  ω   -169.00-119.00   1.00    1.00    -- -109.20 -72.00-144.12   50
 75  ω    -94.00 -69.00   1.00    1.00    -- -109.20  71.00   4.53   25
 76  ω   -111.00 -73.00   1.00    1.00    -- -109.20 -68.00 136.90   38
 77  ω   -188.00 -71.00   1.00    1.00    -- -109.20 -70.00  53.00  117
 78  ω    -98.00 -71.00   1.00    1.00    -- -109.20 -72.00 -37.87   27
 79  ω    -91.00 -66.00   1.00    1.00    -- -109.20  70.00 -21.74   25
 80  ω   -192.00-147.00   1.00    1.00    -- -109.20 -61.00 -35.08   45
 81  ω    -99.00 -73.00   1.00    1.00    -- -109.20 -68.00 177.50   26
 82  ω   -167.00 -79.00   1.00    1.00    -- -109.20 -60.00  84.84   88
 83  ω   -110.00 -69.00   1.00    1.00    -- -109.20 -73.00 112.62   41
 84  ω   -103.00 -77.00   1.00    1.00    -- -109.20 -62.00 -79.18   26
 85  ω    -95.00 -48.00   1.00    1.00    -- -109.20  80.00  -1.52   47
 86  ω   -118.00 -77.00   1.00    1.00    -- -109.20 -63.00 -93.49   41
 87  ω    -97.00 -55.00   1.00    1.00    -- -109.20  80.00  39.76   42
 88  ω    -97.00 -70.00   1.00    1.00    -- -109.20 -72.00  41.47   27
 89  ω   -165.00-115.00   1.00    1.00    -- -109.20 -73.00 112.62   50
 90  ω   -118.00 -71.00   1.00    1.00    -- -109.20 -73.00-118.89   47
 91  ω    -95.00 -69.00   1.00    1.00    -- -109.20 -73.00  92.03   26
 92  ω   -158.00-132.00   1.00    1.00    -- -109.20 -73.00  92.03   26
 93  ω    -99.00 -73.00   1.00    1.00    -- -109.20 -67.00 -55.53   26
 94  ω   -187.00-162.00   1.00    1.00    -- -109.20 -13.00 152.10   25
 95  ω    -97.00 -71.00   1.00    1.00    -- -109.20 -73.00 -25.13   26
 96  ω    -95.00 -70.00   1.00    1.00    -- -109.20 -73.00  75.17   25
 97  ω   -103.00 -77.00   1.00    1.00    -- -109.20 -58.00 -89.33   26
 98  ω    -96.00 -70.00   1.00    1.00    -- -109.20  77.00  90.00   26
 99  ω    -97.00 -71.00   1.00    1.00    -- -109.20 -71.00 123.16   26
100  ω   -150.00-124.00   1.00    1.00    -- -109.20 -37.00  60.00   26
101  ω   -118.00 -73.00   1.00    1.00    -- -109.20 -67.00 158.00   45
102  ω   -172.00-146.00   1.00    1.00    -- -109.20 -58.00 -89.33   26
103  ω   -192.00 -92.00   1.00    1.00    -- -109.20 -48.00-124.93  100
104  ω    -96.00 -70.00   1.00    1.00    -- -109.20  57.00-120.00   26
105  ω   -184.00-117.00   1.00    1.00    -- -109.20 -64.00   8.00   67
106  ω   -119.00 -93.00   1.00    1.00    -- -109.20 -51.00-130.40   26
107  ω   -108.00 -72.00   1.00    1.00    -- -109.20 -71.00-155.43   36
108  ω   -106.00 -79.00   1.00    1.00    -- -109.20 -57.00 -16.88   27
109  ω    -99.00 -72.00   1.00    1.00    -- -109.20 -73.00  35.03   27
110  ω   -123.00 -80.00   1.00    1.00    -- -109.20 -61.00 164.65   43
111  ω   -101.00 -72.00   1.00    1.00    -- -109.20 -70.00 152.62   29
112  ω   -102.00 -75.00   1.00    1.00    -- -109.20 -64.00 -13.52   27
;
_diffrn_measurement_device       'AFC12: Kappa 4 circle'
_diffrn_measurement_device_type  'Rigaku XtaLAB P100K'
_diffrn_measurement_method       'shutterless scans'
_diffrn_measurement_specimen_support Loop
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0030348000
_diffrn_orient_matrix_UB_12      -0.0656417000
_diffrn_orient_matrix_UB_13      0.0465573000
_diffrn_orient_matrix_UB_21      -0.0597411000
_diffrn_orient_matrix_UB_22      -0.0475178000
_diffrn_orient_matrix_UB_23      -0.0913093000
_diffrn_orient_matrix_UB_31      0.0562193000
_diffrn_orient_matrix_UB_32      0.0129350000
_diffrn_orient_matrix_UB_33      -0.0998192000
_diffrn_radiation_monochromator  'Rigaku Osmic Confocal Optical System'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating Anode'
_diffrn_source_type              'Rigaku MM-007HF'
_reflns_Friedel_coverage         0.994
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.992
_reflns_number_gt                3438
_reflns_number_total             3444
_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 1.171.42.82a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.82a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.82a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.172
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details 
;
 Flack x determined using 1700 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.005(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         3444
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0216
_refine_ls_R_factor_gt           0.0215
_refine_ls_restrained_S_all      1.058
_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)+(0.0349P)²+2.5968P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0560
_refine_ls_wR_factor_ref         0.0560
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C6(H6), C30(H30)
2.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C11(H11), C12(H12), C15(H15), C16(H16), C18(H18), C19(H19)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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 0.40451(3) 0.20180(3) 0.61964(5) 0.02919(13) Uani 1 1 d . . . . .
F21 F 0.41548(9) 0.25996(8) 0.90293(14) 0.0463(4) Uani 1 1 d . . . . .
F22 F 0.31023(10) 0.17508(11) 0.94532(15) 0.0602(5) Uani 1 1 d . . . . .
F23 F 0.39099(11) 0.15178(10) 0.88756(15) 0.0553(5) Uani 1 1 d . . . . .
O4 O 0.36080(9) 0.36628(9) 0.76480(15) 0.0328(4) Uani 1 1 d . . . . .
N2 N 0.49431(10) 0.32204(10) 0.50295(17) 0.0266(4) Uani 1 1 d . . . . .
N3 N 0.43677(9) 0.33981(9) 0.66600(15) 0.0215(4) Uani 1 1 d . . . . .
N13 N 0.58243(14) 0.16245(13) 0.0548(2) 0.0438(5) Uani 1 1 d . . . . .
N20 N 0.70306(12) 0.68487(12) 0.6894(2) 0.0437(5) Uani 1 1 d . . . . .
C2 C 0.44909(11) 0.29438(11) 0.58937(19) 0.0220(4) Uani 1 1 d . . . . .
C4 C 0.37089(12) 0.32126(11) 0.71728(18) 0.0230(4) Uani 1 1 d . . . . .
C5 C 0.31361(11) 0.24414(12) 0.7121(2) 0.0265(4) Uani 1 1 d . . . . .
H5A H 0.290583 0.234282 0.629490 0.032 Uiso 1 1 calc R U . . .
H5B H 0.276874 0.235767 0.774969 0.032 Uiso 1 1 calc R U . . .
C6 C 0.33991(12) 0.19176(12) 0.7349(2) 0.0263(4) Uani 1 1 d . . . . .
H6 H 0.297828 0.143046 0.722975 0.032 Uiso 1 1 calc R U . . .
C7 C 0.50701(11) 0.28028(11) 0.4172(2) 0.0254(4) Uani 1 1 d . . . . .
C8 C 0.49104(13) 0.28556(13) 0.2936(2) 0.0323(5) Uani 1 1 d . . . . .
H8 H 0.468620 0.312284 0.272901 0.039 Uiso 1 1 calc R U . . .
C9 C 0.50755(14) 0.25231(14) 0.2015(2) 0.0339(5) Uani 1 1 d . . . . .
H9 H 0.496663 0.256119 0.117403 0.041 Uiso 1 1 calc R U . . .
C10 C 0.54029(12) 0.21301(13) 0.2318(2) 0.0289(5) Uani 1 1 d . . . . .
C11 C 0.55436(13) 0.20546(14) 0.3555(2) 0.0339(5) Uani 1 1 d . . . . .
H11 H 0.574667 0.176834 0.376471 0.041 Uiso 1 1 calc R U . . .
C12 C 0.53854(13) 0.23998(14) 0.4478(2) 0.0324(5) Uani 1 1 d . . . . .
H12 H 0.549237 0.236108 0.532005 0.039 Uiso 1 1 calc R U . . .
C13 C 0.56277(14) 0.18341(13) 0.1341(2) 0.0342(5) Uani 1 1 d . . . . .
C14 C 0.49186(11) 0.41438(11) 0.66850(19) 0.0228(4) Uani 1 1 d . . . . .
C15 C 0.49467(13) 0.46125(13) 0.5784(2) 0.0304(5) Uani 1 1 d . . . . .
H15 H 0.459865 0.445057 0.514380 0.036 Uiso 1 1 calc R U . . .
C16 C 0.54816(14) 0.53153(13) 0.5819(2) 0.0334(5) Uani 1 1 d . . . . .
H16 H 0.550709 0.564015 0.520112 0.040 Uiso 1 1 calc R U . . .
C17 C 0.59864(12) 0.55453(12) 0.6772(2) 0.0267(5) Uani 1 1 d . . . . .
C18 C 0.59484(12) 0.50719(12) 0.7687(2) 0.0282(4) Uani 1 1 d . . . . .
H18 H 0.628664 0.523249 0.834271 0.034 Uiso 1 1 calc R U . . .
C19 C 0.54131(12) 0.43656(12) 0.7629(2) 0.0255(4) Uani 1 1 d . . . . .
H19 H 0.538700 0.403573 0.823722 0.031 Uiso 1 1 calc R U . . .
C20 C 0.65611(13) 0.62784(13) 0.6827(2) 0.0333(5) Uani 1 1 d . . . . .
C21 C 0.36487(14) 0.19468(13) 0.8674(2) 0.0353(5) Uani 1 1 d . . . . .
Cl30 Cl 0.57785(4) 0.28369(4) 0.81498(8) 0.0566(2) Uani 1 1 d . . . . .
C30 C 0.666667 0.333333 0.8655(4) 0.0379(10) Uani 1 3 d S T P . .
H30 H 0.666667 0.333333 0.958357 0.045 Uiso 1 3 calc R U P . .


_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 C2 1.768(2) . ?
S1 C6 1.801(2) . ?
F21 C21 1.341(3) . ?
F22 C21 1.335(3) . ?
F23 C21 1.326(3) . ?
O4 C4 1.214(3) . ?
N2 C2 1.264(3) . ?
N2 C7 1.413(3) . ?
N3 C2 1.409(3) . ?
N3 C4 1.390(3) . ?
N3 C14 1.452(3) . ?
N13 C13 1.145(3) . ?
N20 C20 1.145(3) . ?
C4 C5 1.504(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.523(3) . ?
C6 H6 1.0000 . ?
C6 C21 1.516(3) . ?
C7 C8 1.395(3) . ?
C7 C12 1.391(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.374(4) . ?
C9 H9 0.9500 . ?
C9 C10 1.393(3) . ?
C10 C11 1.395(3) . ?
C10 C13 1.438(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.386(3) . ?
C12 H12 0.9500 . ?
C14 C15 1.384(3) . ?
C14 C19 1.378(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.378(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.398(3) . ?
C17 C18 1.394(3) . ?
C17 C20 1.449(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.385(3) . ?
C19 H19 0.9500 . ?
Cl30 C30 1.7571(16) . ?
C30 H30 1.0000 . ?

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
C2 S1 C6 102.40(10) . . ?
C2 N2 C7 122.02(19) . . ?
C2 N3 C14 116.81(17) . . ?
C4 N3 C2 123.84(17) . . ?
C4 N3 C14 117.95(17) . . ?
N2 C2 S1 121.86(16) . . ?
N2 C2 N3 118.20(19) . . ?
N3 C2 S1 119.88(15) . . ?
O4 C4 N3 120.43(19) . . ?
O4 C4 C5 121.9(2) . . ?
N3 C4 C5 117.68(18) . . ?
C4 C5 H5A 108.7 . . ?
C4 C5 H5B 108.7 . . ?
C4 C5 C6 114.44(18) . . ?
H5A C5 H5B 107.6 . . ?
C6 C5 H5A 108.7 . . ?
C6 C5 H5B 108.7 . . ?
S1 C6 H6 106.4 . . ?
C5 C6 S1 110.92(15) . . ?
C5 C6 H6 106.4 . . ?
C21 C6 S1 113.82(16) . . ?
C21 C6 C5 112.26(19) . . ?
C21 C6 H6 106.4 . . ?
C8 C7 N2 115.8(2) . . ?
C12 C7 N2 124.2(2) . . ?
C12 C7 C8 119.8(2) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 C7 120.3(2) . . ?
C9 C8 H8 119.8 . . ?
C8 C9 H9 120.1 . . ?
C8 C9 C10 119.9(2) . . ?
C10 C9 H9 120.1 . . ?
C9 C10 C11 120.2(2) . . ?
C9 C10 C13 119.4(2) . . ?
C11 C10 C13 120.3(2) . . ?
C10 C11 H11 120.2 . . ?
C12 C11 C10 119.6(2) . . ?
C12 C11 H11 120.2 . . ?
C7 C12 H12 120.0 . . ?
C11 C12 C7 120.1(2) . . ?
C11 C12 H12 120.0 . . ?
N13 C13 C10 177.4(3) . . ?
C15 C14 N3 120.93(19) . . ?
C19 C14 N3 117.72(19) . . ?
C19 C14 C15 121.3(2) . . ?
C14 C15 H15 120.1 . . ?
C16 C15 C14 119.7(2) . . ?
C16 C15 H15 120.1 . . ?
C15 C16 H16 120.3 . . ?
C15 C16 C17 119.3(2) . . ?
C17 C16 H16 120.3 . . ?
C16 C17 C20 120.7(2) . . ?
C18 C17 C16 120.6(2) . . ?
C18 C17 C20 118.7(2) . . ?
C17 C18 H18 120.3 . . ?
C19 C18 C17 119.4(2) . . ?
C19 C18 H18 120.3 . . ?
C14 C19 C18 119.6(2) . . ?
C14 C19 H19 120.2 . . ?
C18 C19 H19 120.2 . . ?
N20 C20 C17 177.4(3) . . ?
F21 C21 C6 113.50(19) . . ?
F22 C21 F21 106.5(2) . . ?
F22 C21 C6 109.7(2) . . ?
F23 C21 F21 106.4(2) . . ?
F23 C21 F22 107.2(2) . . ?
F23 C21 C6 113.2(2) . . ?
Cl30 C30 Cl30 110.87(14) 2_655 . ?
Cl30 C30 Cl30 110.87(14) . 3_665 ?
Cl30 C30 Cl30 110.87(14) 2_655 3_665 ?
Cl30 C30 H30 108.0 2_655 . ?
Cl30 C30 H30 108.0 . . ?
Cl30 C30 H30 108.0 3_665 . ?

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 C6 C21 F21 71.3(2) . . . . ?
S1 C6 C21 F22 -169.69(17) . . . . ?
S1 C6 C21 F23 -50.1(3) . . . . ?
O4 C4 C5 C6 -140.6(2) . . . . ?
N2 C7 C8 C9 174.0(2) . . . . ?
N2 C7 C12 C11 -174.5(2) . . . . ?
N3 C4 C5 C6 39.1(3) . . . . ?
N3 C14 C15 C16 -179.0(2) . . . . ?
N3 C14 C19 C18 179.9(2) . . . . ?
C2 S1 C6 C5 34.01(17) . . . . ?
C2 S1 C6 C21 -93.74(17) . . . . ?
C2 N2 C7 C8 116.9(2) . . . . ?
C2 N2 C7 C12 -68.1(3) . . . . ?
C2 N3 C4 O4 -167.59(19) . . . . ?
C2 N3 C4 C5 12.7(3) . . . . ?
C2 N3 C14 C15 83.7(2) . . . . ?
C2 N3 C14 C19 -95.8(2) . . . . ?
C4 N3 C2 S1 -36.6(3) . . . . ?
C4 N3 C2 N2 146.1(2) . . . . ?
C4 N3 C14 C15 -83.3(3) . . . . ?
C4 N3 C14 C19 97.1(2) . . . . ?
C4 C5 C6 S1 -60.7(2) . . . . ?
C4 C5 C6 C21 67.9(2) . . . . ?
C5 C6 C21 F21 -55.7(3) . . . . ?
C5 C6 C21 F22 63.3(3) . . . . ?
C5 C6 C21 F23 -177.1(2) . . . . ?
C6 S1 C2 N2 -172.66(18) . . . . ?
C6 S1 C2 N3 10.08(18) . . . . ?
C7 N2 C2 S1 6.5(3) . . . . ?
C7 N2 C2 N3 -176.22(19) . . . . ?
C7 C8 C9 C10 0.1(4) . . . . ?
C8 C7 C12 C11 0.3(4) . . . . ?
C8 C9 C10 C11 2.0(4) . . . . ?
C8 C9 C10 C13 -174.8(2) . . . . ?
C9 C10 C11 C12 -2.9(4) . . . . ?
C10 C11 C12 C7 1.8(4) . . . . ?
C12 C7 C8 C9 -1.3(4) . . . . ?
C13 C10 C11 C12 173.8(2) . . . . ?
C14 N3 C2 S1 157.21(15) . . . . ?
C14 N3 C2 N2 -20.2(3) . . . . ?
C14 N3 C4 O4 -1.5(3) . . . . ?
C14 N3 C4 C5 178.82(18) . . . . ?
C14 C15 C16 C17 -0.4(4) . . . . ?
C15 C14 C19 C18 0.3(3) . . . . ?
C15 C16 C17 C18 -0.5(4) . . . . ?
C15 C16 C17 C20 179.2(2) . . . . ?
C16 C17 C18 C19 1.3(3) . . . . ?
C17 C18 C19 C14 -1.2(3) . . . . ?
C19 C14 C15 C16 0.5(3) . . . . ?
C20 C17 C18 C19 -178.4(2) . . . . ?

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Hexanes into chloroform'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_65
_database_code_depnum_ccdc_archive 'CCDC 2410989'
loop_
_audit_author_name
_audit_author_address
'Aidan McKay'
;University of St Andews
United Kingdom
;
_audit_update_record             
;
2024-12-17 deposited with the CCDC.	2025-04-30 downloaded from the CCDC.
;
_audit_creation_date             2024-08-14
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        
(R,Z)-N-(3-(2-isopropylphenyl)-4-oxo-6-(trifluoromethyl)-1,3-thiazinan-2-ylidene)-4-methylbenzenesulfonamide
_chemical_formula_moiety         'C21 H21 F3 N2 O3 S2'
_chemical_formula_sum            'C21 H21 F3 N2 O3 S2'
_chemical_formula_weight         470.52
_chemical_absolute_configuration ad
_chemical_melting_point          ?
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'
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'
F F 0.0727 0.0534 '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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   8.07483(6)
_cell_length_b                   15.56758(15)
_cell_length_c                   17.59729(15)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2212.08(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    25525
_cell_measurement_temperature    100
_cell_measurement_theta_max      75.1030
_cell_measurement_theta_min      3.7570
_shelx_estimated_absorpt_T_max   0.982
_shelx_estimated_absorpt_T_min   0.352
_exptl_absorpt_coefficient_mu    2.639
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.34631
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.109a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.413
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.025
_exptl_crystal_size_min          0.007
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0938
_diffrn_reflns_av_unetI/netI     0.0368
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            43774
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.584
_diffrn_reflns_theta_min         3.791
_diffrn_ambient_temperature      100
_diffrn_detector                 'hybrid photon counting detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Dectris PILATUS P200K'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -89.00  89.00   0.50    0.50    --    0.00  28.00 -60.00  356
  2  ω    -84.00  94.00   0.50    0.50    --    5.00  18.00 120.00  356
  3  ω   -185.00  -8.00   0.50    4.00    --  -96.50  37.00-150.00  354
  4  ω   -185.00  -8.00   0.50    4.00    --  -96.50   0.00  90.00  354
  5  ω   -185.00  -8.00   0.50    4.00    --  -96.50  46.00 -90.00  354
  6  ω   -185.00  -8.00   0.50    4.00    --  -96.50  46.00  90.00  354
  7  ω   -185.00  -8.00   0.50    4.00    --  -96.50  46.00-150.00  354
  8  ω   -185.00  -8.00   0.50    4.00    --  -96.50  46.00 120.00  354
  9  ω   -185.00  -8.00   0.50    4.00    --  -96.50  46.00-180.00  354
 10  ω   -185.00  -8.00   0.50    4.00    --  -96.50   0.00  90.00  354
 11  ω   -185.00  -8.00   0.50    4.00    --  -96.50   9.00 -60.00  354
 12  ω   -185.00  -8.00   0.50    4.00    --  -96.50  46.00 150.00  354
 13  ω   -185.00  -8.00   0.50    4.00    --  -96.50  46.00-120.00  354
 14  ω   -185.00  -8.00   0.50    4.00    --  -96.50  46.00  60.00  354
;
_diffrn_measurement_device       'AFC11: Quarter χ 4 circle'
_diffrn_measurement_device_type  'Rigaku XtaLAB P200K'
_diffrn_measurement_method       'shutterless scans'
_diffrn_measurement_specimen_support Loop
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0845322000
_diffrn_orient_matrix_UB_12      -0.0276044000
_diffrn_orient_matrix_UB_13      0.0746085000
_diffrn_orient_matrix_UB_21      0.1158957000
_diffrn_orient_matrix_UB_22      -0.0784095000
_diffrn_orient_matrix_UB_23      0.0050171000
_diffrn_orient_matrix_UB_31      0.1257238000
_diffrn_orient_matrix_UB_32      0.0537066000
_diffrn_orient_matrix_UB_33      0.0455487000
_diffrn_radiation_monochromator  'Rigaku Osmic Confocal Optical System'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating Anode'
_diffrn_source_type              'Rigaku MM-007HF'
_reflns_Friedel_coverage         0.747
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.988
_reflns_number_gt                4432
_reflns_number_total             4547
_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 1.171.43.109a (Rigaku OD, 2024)'
_computing_data_collection       
'CrysAlisPro system (CCD 42.94a (release 21-06-2023))'
_computing_data_reduction        'CrysAlisPro 1.171.43.109a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.692
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.069
_refine_ls_abs_structure_details 
;
 Flack x determined using 1829 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.008(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         4547
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0394
_refine_ls_R_factor_gt           0.0386
_refine_ls_restrained_S_all      1.043
_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)+(0.0708P)²+0.5635P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1028
_refine_ls_wR_factor_ref         0.1033
_refine_special_details          ?
_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 Ternary CH refined with riding coordinates:
 C20(H20), C6(H6)
2.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B)
2.c Aromatic/amide H refined with riding coordinates:
 C16(H16), C19(H19), C17(H17), C18(H18), C12(H12), C8(H8), C9(H9), C11(H11)
2.d Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C21(H21A,H21B,H21C), C13(H13A,H13B,H13C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
S3 S 0.41341(7) 0.62033(4) 0.50127(4) 0.02196(17) Uani 1 1 d . . . . .
S1 S 0.78734(8) 0.62605(5) 0.45668(4) 0.02560(18) Uani 1 1 d . . . . .
O3 O 0.5138(3) 0.65311(14) 0.56249(12) 0.0265(4) Uani 1 1 d . . . . .
F1 F 0.7934(3) 0.51049(13) 0.31256(14) 0.0480(6) Uani 1 1 d . . . . .
F2 F 0.9310(3) 0.45455(14) 0.40494(15) 0.0543(6) Uani 1 1 d . . . . .
O2 O 0.2379(2) 0.63689(14) 0.50479(12) 0.0280(4) Uani 1 1 d . . . . .
O4 O 0.8127(3) 0.71378(16) 0.22001(12) 0.0323(5) Uani 1 1 d . . . . .
F3 F 1.0593(3) 0.50157(16) 0.30608(14) 0.0554(6) Uani 1 1 d . . . . .
N3 N 0.6538(3) 0.68627(15) 0.32321(14) 0.0222(5) Uani 1 1 d . . . . .
N2 N 0.4719(3) 0.65869(15) 0.41846(13) 0.0224(5) Uani 1 1 d . . . . .
C14 C 0.5106(3) 0.70761(19) 0.27701(16) 0.0231(5) Uani 1 1 d . . . . .
C20 C 0.5190(3) 0.85953(18) 0.32976(16) 0.0246(6) Uani 1 1 d . . . . .
H20 H 0.564873 0.830683 0.375976 0.029 Uiso 1 1 calc R U . . .
C16 C 0.3106(4) 0.8059(2) 0.23109(18) 0.0291(6) Uani 1 1 d . . . . .
H16 H 0.262718 0.861594 0.230405 0.035 Uiso 1 1 calc R U . . .
C19 C 0.4448(4) 0.64321(19) 0.23129(16) 0.0260(6) Uani 1 1 d . . . . .
H19 H 0.491658 0.587237 0.232058 0.031 Uiso 1 1 calc R U . . .
C17 C 0.2449(4) 0.7429(2) 0.18478(18) 0.0306(7) Uani 1 1 d . . . . .
H17 H 0.153661 0.755929 0.152713 0.037 Uiso 1 1 calc R U . . .
C18 C 0.3113(4) 0.6608(2) 0.18478(18) 0.0294(6) Uani 1 1 d . . . . .
H18 H 0.265640 0.617241 0.153273 0.035 Uiso 1 1 calc R U . . .
C4 C 0.8092(4) 0.69327(19) 0.28635(17) 0.0254(6) Uani 1 1 d . . . . .
C12 C 0.3799(4) 0.4634(2) 0.43297(17) 0.0284(6) Uani 1 1 d . . . . .
H12 H 0.328182 0.493443 0.392442 0.034 Uiso 1 1 calc R U . . .
C8 C 0.5213(4) 0.4644(2) 0.55389(17) 0.0277(6) Uani 1 1 d . . . . .
H8 H 0.566230 0.495117 0.595720 0.033 Uiso 1 1 calc R U . . .
C7 C 0.4424(3) 0.50813(18) 0.49487(16) 0.0239(5) Uani 1 1 d . . . . .
C15 C 0.4456(3) 0.79004(18) 0.27904(15) 0.0229(5) Uani 1 1 d . . . . .
C2 C 0.6250(3) 0.65808(18) 0.39676(17) 0.0224(5) Uani 1 1 d . . . . .
C23 C 0.9336(4) 0.5176(2) 0.3537(2) 0.0375(7) Uani 1 1 d . . . . .
C10 C 0.4686(4) 0.3297(2) 0.48993(18) 0.0307(6) Uani 1 1 d . . . . .
C9 C 0.5332(4) 0.3758(2) 0.55080(18) 0.0302(6) Uani 1 1 d . . . . .
H9 H 0.586553 0.345855 0.590987 0.036 Uiso 1 1 calc R U . . .
C22 C 0.6621(4) 0.9063(2) 0.2905(2) 0.0326(7) Uani 1 1 d . . . . .
H22A H 0.747355 0.864680 0.275920 0.049 Uiso 1 1 calc R U . . .
H22B H 0.709676 0.948711 0.325371 0.049 Uiso 1 1 calc R U . . .
H22C H 0.620701 0.935573 0.244944 0.049 Uiso 1 1 calc R U . . .
C6 C 0.9510(3) 0.6055(2) 0.38917(18) 0.0278(6) Uani 1 1 d . . . . .
H6 H 1.057283 0.605302 0.418375 0.033 Uiso 1 1 calc R U . . .
C11 C 0.3933(4) 0.3749(2) 0.43049(18) 0.0327(6) Uani 1 1 d . . . . .
H11 H 0.350805 0.344388 0.387976 0.039 Uiso 1 1 calc R U . . .
C21 C 0.3897(4) 0.9245(2) 0.35630(18) 0.0293(6) Uani 1 1 d . . . . .
H21A H 0.355185 0.960156 0.313233 0.044 Uiso 1 1 calc R U . . .
H21B H 0.437461 0.961056 0.395964 0.044 Uiso 1 1 calc R U . . .
H21C H 0.293386 0.893901 0.376721 0.044 Uiso 1 1 calc R U . . .
C5 C 0.9636(3) 0.6769(2) 0.33138(17) 0.0281(6) Uani 1 1 d . . . . .
H5A H 0.994250 0.730540 0.358172 0.034 Uiso 1 1 calc R U . . .
H5B H 1.054373 0.663088 0.295628 0.034 Uiso 1 1 calc R U . . .
C13 C 0.4767(5) 0.2327(2) 0.4876(2) 0.0412(8) Uani 1 1 d . . . . .
H13A H 0.574148 0.212973 0.515862 0.062 Uiso 1 1 calc R U . . .
H13B H 0.484618 0.213424 0.434729 0.062 Uiso 1 1 calc R U . . .
H13C H 0.376437 0.208703 0.510813 0.062 Uiso 1 1 calc R U . . .


_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
S3 O3 1.441(2) . ?
S3 O2 1.442(2) . ?
S3 N2 1.644(2) . ?
S3 C7 1.766(3) . ?
S1 C2 1.755(3) . ?
S1 C6 1.806(3) . ?
F1 C23 1.348(4) . ?
F2 C23 1.333(5) . ?
O4 C4 1.211(4) . ?
F3 C23 1.340(4) . ?
N3 C14 1.452(4) . ?
N3 C4 1.416(3) . ?
N3 C2 1.386(4) . ?
N2 C2 1.294(4) . ?
C14 C19 1.391(4) . ?
C14 C15 1.387(4) . ?
C20 H20 1.0000 . ?
C20 C15 1.523(4) . ?
C20 C22 1.531(4) . ?
C20 C21 1.527(4) . ?
C16 H16 0.9500 . ?
C16 C17 1.380(5) . ?
C16 C15 1.400(4) . ?
C19 H19 0.9500 . ?
C19 C18 1.381(4) . ?
C17 H17 0.9500 . ?
C17 C18 1.386(5) . ?
C18 H18 0.9500 . ?
C4 C5 1.499(4) . ?
C12 H12 0.9500 . ?
C12 C7 1.388(4) . ?
C12 C11 1.382(5) . ?
C8 H8 0.9500 . ?
C8 C7 1.395(4) . ?
C8 C9 1.384(4) . ?
C23 C6 1.510(4) . ?
C10 C9 1.390(5) . ?
C10 C11 1.399(5) . ?
C10 C13 1.513(4) . ?
C9 H9 0.9500 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C6 H6 1.0000 . ?
C6 C5 1.511(5) . ?
C11 H11 0.9500 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?

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
O3 S3 O2 117.21(13) . . ?
O3 S3 N2 111.87(13) . . ?
O3 S3 C7 108.87(13) . . ?
O2 S3 N2 104.79(12) . . ?
O2 S3 C7 108.06(13) . . ?
N2 S3 C7 105.35(13) . . ?
C2 S1 C6 101.64(14) . . ?
C4 N3 C14 115.6(2) . . ?
C2 N3 C14 117.5(2) . . ?
C2 N3 C4 126.9(2) . . ?
C2 N2 S3 122.2(2) . . ?
C19 C14 N3 117.6(3) . . ?
C15 C14 N3 119.9(3) . . ?
C15 C14 C19 122.5(3) . . ?
C15 C20 H20 107.6 . . ?
C15 C20 C22 111.5(2) . . ?
C15 C20 C21 112.5(2) . . ?
C22 C20 H20 107.6 . . ?
C21 C20 H20 107.6 . . ?
C21 C20 C22 109.8(2) . . ?
C17 C16 H16 119.0 . . ?
C17 C16 C15 122.0(3) . . ?
C15 C16 H16 119.0 . . ?
C14 C19 H19 120.1 . . ?
C18 C19 C14 119.9(3) . . ?
C18 C19 H19 120.1 . . ?
C16 C17 H17 119.8 . . ?
C16 C17 C18 120.4(3) . . ?
C18 C17 H17 119.8 . . ?
C19 C18 C17 119.0(3) . . ?
C19 C18 H18 120.5 . . ?
C17 C18 H18 120.5 . . ?
O4 C4 N3 118.9(3) . . ?
O4 C4 C5 122.3(3) . . ?
N3 C4 C5 118.8(2) . . ?
C7 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C11 C12 C7 119.8(3) . . ?
C7 C8 H8 120.4 . . ?
C9 C8 H8 120.4 . . ?
C9 C8 C7 119.3(3) . . ?
C12 C7 S3 119.9(2) . . ?
C12 C7 C8 120.3(3) . . ?
C8 C7 S3 119.7(2) . . ?
C14 C15 C20 121.7(2) . . ?
C14 C15 C16 116.2(3) . . ?
C16 C15 C20 122.1(3) . . ?
N3 C2 S1 121.7(2) . . ?
N2 C2 S1 122.6(2) . . ?
N2 C2 N3 115.7(3) . . ?
F1 C23 C6 112.0(2) . . ?
F2 C23 F1 106.8(3) . . ?
F2 C23 F3 107.3(3) . . ?
F2 C23 C6 112.8(3) . . ?
F3 C23 F1 106.6(3) . . ?
F3 C23 C6 110.9(3) . . ?
C9 C10 C11 118.7(3) . . ?
C9 C10 C13 121.3(3) . . ?
C11 C10 C13 120.0(3) . . ?
C8 C9 C10 121.2(3) . . ?
C8 C9 H9 119.4 . . ?
C10 C9 H9 119.4 . . ?
C20 C22 H22A 109.5 . . ?
C20 C22 H22B 109.5 . . ?
C20 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
S1 C6 H6 106.9 . . ?
C23 C6 S1 111.4(2) . . ?
C23 C6 H6 106.9 . . ?
C23 C6 C5 113.2(3) . . ?
C5 C6 S1 111.2(2) . . ?
C5 C6 H6 106.9 . . ?
C12 C11 C10 120.7(3) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C4 C5 C6 115.2(2) . . ?
C4 C5 H5A 108.5 . . ?
C4 C5 H5B 108.5 . . ?
C6 C5 H5A 108.5 . . ?
C6 C5 H5B 108.5 . . ?
H5A C5 H5B 107.5 . . ?
C10 C13 H13A 109.5 . . ?
C10 C13 H13B 109.5 . . ?
C10 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?

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
S3 N2 C2 S1 -6.3(4) . . . . ?
S3 N2 C2 N3 175.06(19) . . . . ?
S1 C6 C5 C4 -58.2(3) . . . . ?
O3 S3 N2 C2 49.2(3) . . . . ?
O3 S3 C7 C12 -169.8(2) . . . . ?
O3 S3 C7 C8 13.2(3) . . . . ?
F1 C23 C6 S1 63.6(4) . . . . ?
F1 C23 C6 C5 -62.6(4) . . . . ?
F2 C23 C6 S1 -57.0(3) . . . . ?
F2 C23 C6 C5 176.8(3) . . . . ?
O2 S3 N2 C2 177.2(2) . . . . ?
O2 S3 C7 C12 61.9(3) . . . . ?
O2 S3 C7 C8 -115.1(2) . . . . ?
O4 C4 C5 C6 -143.8(3) . . . . ?
F3 C23 C6 S1 -177.4(2) . . . . ?
F3 C23 C6 C5 56.4(3) . . . . ?
N3 C14 C19 C18 -178.3(3) . . . . ?
N3 C14 C15 C20 -0.9(4) . . . . ?
N3 C14 C15 C16 178.2(2) . . . . ?
N3 C4 C5 C6 37.6(4) . . . . ?
N2 S3 C7 C12 -49.7(3) . . . . ?
N2 S3 C7 C8 133.3(2) . . . . ?
C14 N3 C4 O4 -1.9(4) . . . . ?
C14 N3 C4 C5 176.7(3) . . . . ?
C14 N3 C2 S1 177.3(2) . . . . ?
C14 N3 C2 N2 -4.1(4) . . . . ?
C14 C19 C18 C17 -0.1(4) . . . . ?
C16 C17 C18 C19 -0.5(5) . . . . ?
C19 C14 C15 C20 179.7(3) . . . . ?
C19 C14 C15 C16 -1.2(4) . . . . ?
C17 C16 C15 C14 0.5(4) . . . . ?
C17 C16 C15 C20 179.6(3) . . . . ?
C4 N3 C14 C19 84.9(3) . . . . ?
C4 N3 C14 C15 -94.5(3) . . . . ?
C4 N3 C2 S1 0.2(4) . . . . ?
C4 N3 C2 N2 178.8(3) . . . . ?
C7 S3 N2 C2 -68.9(3) . . . . ?
C7 C12 C11 C10 0.3(4) . . . . ?
C7 C8 C9 C10 0.2(4) . . . . ?
C15 C14 C19 C18 1.0(4) . . . . ?
C15 C16 C17 C18 0.4(5) . . . . ?
C2 S1 C6 C23 -81.5(2) . . . . ?
C2 S1 C6 C5 45.8(2) . . . . ?
C2 N3 C14 C19 -92.5(3) . . . . ?
C2 N3 C14 C15 88.1(3) . . . . ?
C2 N3 C4 O4 175.2(3) . . . . ?
C2 N3 C4 C5 -6.1(4) . . . . ?
C23 C6 C5 C4 68.1(3) . . . . ?
C9 C8 C7 S3 175.6(2) . . . . ?
C9 C8 C7 C12 -1.4(4) . . . . ?
C9 C10 C11 C12 -1.4(4) . . . . ?
C22 C20 C15 C14 86.4(3) . . . . ?
C22 C20 C15 C16 -92.6(3) . . . . ?
C6 S1 C2 N3 -19.2(3) . . . . ?
C6 S1 C2 N2 162.3(3) . . . . ?
C11 C12 C7 S3 -175.8(2) . . . . ?
C11 C12 C7 C8 1.2(4) . . . . ?
C11 C10 C9 C8 1.2(4) . . . . ?
C21 C20 C15 C14 -149.6(3) . . . . ?
C21 C20 C15 C16 31.3(4) . . . . ?
C13 C10 C9 C8 -178.0(3) . . . . ?
C13 C10 C11 C12 177.8(3) . . . . ?


##==END CIF 3 of 3
##==END COMBINED CIF
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Hexane into ethyl acetate'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_53
_database_code_depnum_ccdc_archive 'CCDC 2410988'
loop_
_audit_author_name
_audit_author_address
'Aidan McKay'
;University of St Andews
United Kingdom
;
_audit_update_record             
;
2024-12-17 deposited with the CCDC.	2025-04-30 downloaded from the CCDC.
;
_audit_creation_date             2024-07-08
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        
;
(R,Z)-N-(4-oxo-3-phenyl-6-(trifluoromethyl)-1,3-selenazinan-2-ylidene)benzamide
;
_chemical_formula_moiety         'C18 H13 F3 N2 O2 Se'
_chemical_formula_sum            'C18 H13 F3 N2 O2 Se'
_chemical_formula_weight         425.26
_chemical_absolute_configuration ad
_chemical_melting_point          ?
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'
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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.7943 1.1372 '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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   9.51115(5)
_cell_length_b                   16.17558(9)
_cell_length_c                   10.71507(5)
_cell_angle_alpha                90
_cell_angle_beta                 91.4505(5)
_cell_angle_gamma                90
_cell_volume                     1647.968(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    43241
_cell_measurement_temperature    100
_cell_measurement_theta_max      74.9910
_cell_measurement_theta_min      4.6210
_shelx_estimated_absorpt_T_max   0.965
_shelx_estimated_absorpt_T_min   0.741
_exptl_absorpt_coefficient_mu    3.538
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72712
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.109a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.714
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0709
_diffrn_reflns_av_unetI/netI     0.0274
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            61612
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.618
_diffrn_reflns_theta_min         4.127
_diffrn_ambient_temperature      100
_diffrn_detector                 'hybrid photon counting detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Dectris PILATUS P200K'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -89.00  89.00   0.50    0.50    --    0.00  25.00 -35.00  356
  2  ω    -89.00  89.00   0.50    0.50    --    0.00  25.00 -35.00  356
  3  ω    -84.00  94.00   0.50    0.50    --    5.00  55.00 -43.94  356
  4  ω    -84.00  94.00   0.50    0.50    --    5.00  25.00 -35.00  356
  5  ω   -129.00  49.00   0.50    0.50    --  -40.00  55.00-179.28  356
  6  ω   -133.00  45.00   0.50    0.50    --  -44.00  55.00 -46.51  356
  7  ω   -133.00  45.00   0.50    0.50    --  -44.00  55.00  76.52  356
  8  ω   -137.00  41.00   0.50    0.50    --  -48.00  54.00  19.81  356
  9  ω   -145.00  33.00   0.50    0.50    --  -56.00  55.00-109.87  356
 10  ω   -145.00  33.00   0.50    0.50    --  -56.00  55.00 -70.27  356
 11  ω   -149.00  29.00   0.50    0.50    --  -60.00  55.00  75.62  356
 12  ω   -149.00  29.00   0.50    0.50    --  -60.00  54.00 160.15  356
 13  ω   -149.00  29.00   0.50    0.50    --  -60.00  55.00  32.92  356
 14  ω     -1.00  25.00   0.50    0.50    --  -64.00  55.00 136.39   52
 15  ω     -4.00  25.00   0.50    0.50    --  -64.00  55.00   3.11   58
 16  ω     -8.00  18.00   0.50    0.50    --  -68.00  55.00 -40.17   52
 17  ω    -11.00  20.00   0.50    0.50    --  -68.00  55.00-141.33   62
 18  ω     -9.00  19.00   0.50    0.50    --  -68.00  54.00 129.77   56
 19  ω    -18.00  17.00   0.50    0.50    --  -72.00  55.00 113.88   70
 20  ω    -11.00  15.00   0.50    0.50    --  -72.00  55.00 -55.89   52
 21  ω    -10.00  17.00   0.50    0.50    --  -72.00  55.00-115.04   54
 22  ω   -118.00 -52.00   0.50    0.50    --  -76.00  55.00-148.90  132
 23  ω    -14.00  12.00   0.50    0.50    --  -76.00  55.00-163.05   52
 24  ω    -24.00  12.00   0.50    0.50    --  -76.00  55.00  87.17   72
 25  ω    -16.00  12.00   0.50    0.50    --  -76.00  55.00   8.47   56
 26  ω    -74.00 -48.00   0.50    0.50    --  -76.00  55.00  87.17   52
 27  ω    -19.00  13.00   0.50    0.50    --  -76.00  55.00  41.74   64
 28  ω    -48.00  13.00   0.50    0.50    --  -76.00  55.00-148.90  122
 29  ω    -17.00  13.00   0.50    0.50    --  -76.00  55.00 -73.60   60
 30  ω   -118.00 -39.00   0.50    0.50    --  -76.00  55.00  41.74  158
 31  ω    -14.00  12.00   0.50    0.50    --  -76.00  52.00 -19.26   52
 32  ω   -143.00   8.00   0.50    0.50    --  -80.00  55.00  77.55  302
 33  ω    -23.00   5.00   0.50    0.50    --  -84.00  54.00 132.88   56
 34  ω   -133.00 -29.00   0.50    0.50    --  -84.00  54.00 132.88  208
 35  ω    -43.00  -3.00   0.50    0.50    --  -84.00  51.00 -80.26   80
 36  ω   -110.00 -84.00   0.50    0.50    --  -84.00  51.00 -80.26   52
 37  ω   -131.00  -3.00   0.50    0.50    --  -92.00  53.00 -22.53  256
 38  ω   -109.00 -83.00   0.50    0.50    --  -96.50  54.00-163.32   52
 39  ω   -183.00  -9.00   0.50    0.50    --  -96.50  55.00  33.10  348
 40  ω   -139.00  -8.00   0.50    0.50    --  -96.50  54.00 163.58  262
 41  ω   -163.00-136.00   0.50    0.50    --  -96.50  54.00-163.32   54
 42  ω   -147.00  -8.00   0.50    0.50    --  -96.50  53.00-119.00  278
 43  ω   -123.00  -8.00   0.50    0.50    --  -96.50  55.00 -47.33  230
 44  ω   -179.00-152.00   0.50    0.50    --  -96.50  55.00 -47.33   54
 45  ω   -120.00 -10.00   0.50    0.50    --  -96.50  54.00-170.94  220
 46  ω   -185.00-124.00   0.50    0.50    --  -96.50  54.00-170.94  122
 47  ω   -184.00 -11.00   0.50    0.50    --  -96.50  55.00  67.50  346
 48  ω    -39.00  -9.00   0.50    0.50    --  -96.50  55.00 120.66   60
 49  ω   -178.00 -45.00   0.50    0.50    --  -96.50  55.00 120.66  266
 50  ω   -185.00  -8.00   0.50    0.50    --  -96.50  55.00 -97.91  354
 51  ω    -42.00  -8.00   0.50    0.50    --  -96.50  55.00  -0.89   68
 52  ω   -114.00 -49.00   0.50    0.50    --  -96.50  55.00  -0.89  130
 53  ω    -49.00  -9.00   0.50    0.50    --  -96.50  54.00-163.32   80
 54  ω   -176.00-129.00   0.50    0.50    --  -96.50  55.00  -0.89   94
 55  ω    -82.00 -54.00   0.50    0.50    --  -96.50  54.00-163.32   56
 56  ω    -53.00 -27.00   0.50    0.50    --  -96.50  25.00 -35.00   52
 57  ω   -132.00-106.00   0.50    0.50    --  -96.50  25.00 -35.00   52
;
_diffrn_measurement_device       'AFC11: Quarter χ 4 circle'
_diffrn_measurement_device_type  'Rigaku XtaLAB P200K'
_diffrn_measurement_method       'shutterless scans'
_diffrn_measurement_specimen_support Loop
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0314904000
_diffrn_orient_matrix_UB_12      0.0236236000
_diffrn_orient_matrix_UB_13      0.1356913000
_diffrn_orient_matrix_UB_21      0.1508083000
_diffrn_orient_matrix_UB_22      0.0335069000
_diffrn_orient_matrix_UB_23      0.0175452000
_diffrn_orient_matrix_UB_31      -0.0501841000
_diffrn_orient_matrix_UB_32      0.0859846000
_diffrn_orient_matrix_UB_33      -0.0442292000
_diffrn_radiation_monochromator  'Rigaku Osmic Confocal Optical System'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating Anode'
_diffrn_source_type              'Rigaku MM-007HF'
_reflns_Friedel_coverage         0.899
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.956
_reflns_number_gt                6489
_reflns_number_total             6656
_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 1.171.43.109a (Rigaku OD, 2024)'
_computing_data_collection       
'CrysAlisPro system (CCD 42.94a (release 21-06-2023))'
_computing_data_reduction        'CrysAlisPro 1.171.43.109a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.437
_refine_diff_density_min         -0.502
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details 
;
 Flack x determined using 3000 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.046(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     469
_refine_ls_number_reflns         6656
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0285
_refine_ls_R_factor_gt           0.0280
_refine_ls_restrained_S_all      1.070
_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)+(0.0547P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0752
_refine_ls_wR_factor_ref         0.0755
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C6(H6), C26(H26)
2.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C25(H25A,H25B)
2.c Aromatic/amide H refined with riding coordinates:
 C15(H15), C16(H16), C17(H17), C18(H18), C19(H19), C9(H9), C10(H10), C11(H11),
 C12(H12), C13(H13), C35(H35), C36(H36), C37(H37), C38(H38), C39(H39), C29(H29),
  C30(H30), C31(H31), C32(H32), C33(H33)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
Se1 Se 0.27985(4) 0.46041(2) 0.64467(3) 0.01966(11) Uani 1 1 d . . . . .
Se21 Se 0.73409(4) 0.53525(2) 0.85842(3) 0.01889(11) Uani 1 1 d . . . . .
F1 F 0.0136(2) 0.39176(15) 0.46706(19) 0.0268(5) Uani 1 1 d . . . . .
F2 F -0.0473(3) 0.42825(14) 0.6515(2) 0.0308(5) Uani 1 1 d . . . . .
F3 F -0.0516(2) 0.29949(15) 0.5991(2) 0.0332(6) Uani 1 1 d . . . . .
F21 F 0.4118(2) 0.58309(14) 0.86599(19) 0.0246(5) Uani 1 1 d . . . . .
F22 F 0.4319(2) 0.71265(15) 0.9085(2) 0.0310(5) Uani 1 1 d . . . . .
F23 F 0.4998(2) 0.62165(15) 1.04329(19) 0.0279(5) Uani 1 1 d . . . . .
O4 O 0.2705(3) 0.26180(16) 0.3496(2) 0.0219(5) Uani 1 1 d . . . . .
O7 O 0.4446(3) 0.59265(17) 0.6102(2) 0.0328(7) Uani 1 1 d . . . . .
O24 O 0.7761(3) 0.7391(2) 1.1434(2) 0.0255(7) Uani 1 1 d . . . . .
O27 O 0.8644(3) 0.39564(18) 0.8915(2) 0.0344(7) Uani 1 1 d . . . . .
N3 N 0.3145(3) 0.39526(18) 0.3963(2) 0.0162(6) Uani 1 1 d . . . . .
N2 N 0.3841(3) 0.52958(19) 0.4242(3) 0.0191(6) Uani 1 1 d . . . . .
N23 N 0.8065(3) 0.60352(18) 1.1005(3) 0.0172(6) Uani 1 1 d . . . . .
N22 N 0.8618(3) 0.46743(18) 1.0772(3) 0.0184(6) Uani 1 1 d . . . . .
C6 C 0.1700(4) 0.3583(2) 0.6363(3) 0.0180(7) Uani 1 1 d . . . . .
H6 H 0.163685 0.337629 0.723947 0.022 Uiso 1 1 calc R U . . .
C5 C 0.2488(4) 0.2931(2) 0.5649(3) 0.0174(7) Uani 1 1 d . . . . .
H5A H 0.194533 0.240936 0.567160 0.021 Uiso 1 1 calc R U . . .
H5B H 0.340226 0.283058 0.608457 0.021 Uiso 1 1 calc R U . . .
C4 C 0.2763(4) 0.3140(2) 0.4298(3) 0.0174(7) Uani 1 1 d . . . . .
C2 C 0.3332(3) 0.4637(2) 0.4736(3) 0.0179(7) Uani 1 1 d . . . . .
C20 C 0.0217(4) 0.3705(2) 0.5888(3) 0.0231(7) Uani 1 1 d . . . . .
C14 C 0.3377(4) 0.4075(2) 0.2629(3) 0.0166(7) Uani 1 1 d . . . . .
C15 C 0.2250(4) 0.4310(2) 0.1873(3) 0.0203(7) Uani 1 1 d . . . . .
H15 H 0.135745 0.441461 0.221818 0.024 Uiso 1 1 calc R U . . .
C16 C 0.2447(4) 0.4391(2) 0.0593(3) 0.0238(8) Uani 1 1 d . . . . .
H16 H 0.168810 0.455853 0.005830 0.029 Uiso 1 1 calc R U . . .
C17 C 0.3754(4) 0.4226(2) 0.0102(3) 0.0239(8) Uani 1 1 d . . . . .
H17 H 0.387831 0.426609 -0.077252 0.029 Uiso 1 1 calc R U . . .
C18 C 0.4879(4) 0.4003(2) 0.0880(3) 0.0233(8) Uani 1 1 d . . . . .
H18 H 0.577659 0.390377 0.054098 0.028 Uiso 1 1 calc R U . . .
C19 C 0.4687(4) 0.3926(2) 0.2161(3) 0.0191(7) Uani 1 1 d . . . . .
H19 H 0.544959 0.377335 0.270223 0.023 Uiso 1 1 calc R U . . .
C7 C 0.4106(4) 0.5985(2) 0.5000(3) 0.0211(7) Uani 1 1 d . . . . .
C8 C 0.3977(4) 0.6795(2) 0.4365(3) 0.0187(7) Uani 1 1 d . . . . .
C9 C 0.3918(4) 0.6861(2) 0.3065(3) 0.0216(7) Uani 1 1 d . . . . .
H9 H 0.394265 0.637977 0.255861 0.026 Uiso 1 1 calc R U . . .
C10 C 0.3825(4) 0.7639(2) 0.2520(4) 0.0260(8) Uani 1 1 d . . . . .
H10 H 0.381990 0.769003 0.163646 0.031 Uiso 1 1 calc R U . . .
C11 C 0.3737(4) 0.8343(3) 0.3258(4) 0.0281(9) Uani 1 1 d . . . . .
H11 H 0.365107 0.887180 0.287915 0.034 Uiso 1 1 calc R U . . .
C12 C 0.3776(4) 0.8271(2) 0.4546(4) 0.0257(8) Uani 1 1 d . . . . .
H12 H 0.370943 0.875169 0.504941 0.031 Uiso 1 1 calc R U . . .
C13 C 0.3912(4) 0.7507(2) 0.5101(3) 0.0214(7) Uani 1 1 d . . . . .
H13 H 0.396116 0.746382 0.598476 0.026 Uiso 1 1 calc R U . . .
C26 C 0.6407(4) 0.6427(2) 0.8654(3) 0.0168(7) Uani 1 1 d . . . . .
H26 H 0.627827 0.662054 0.777192 0.020 Uiso 1 1 calc R U . . .
C25 C 0.7356(4) 0.7051(2) 0.9308(3) 0.0176(7) Uani 1 1 d . . . . .
H25A H 0.823976 0.709348 0.884322 0.021 Uiso 1 1 calc R U . . .
H25B H 0.689206 0.759843 0.927154 0.021 Uiso 1 1 calc R U . . .
C24 C 0.7720(4) 0.6854(2) 1.0650(3) 0.0186(7) Uani 1 1 d . . . . .
C22 C 0.8100(3) 0.5338(2) 1.0269(3) 0.0159(6) Uani 1 1 d . . . . .
C40 C 0.4961(4) 0.6392(2) 0.9198(3) 0.0202(7) Uani 1 1 d . . . . .
C34 C 0.8416(4) 0.5930(2) 1.2333(3) 0.0167(7) Uani 1 1 d . . . . .
C35 C 0.7365(4) 0.5674(2) 1.3117(3) 0.0207(7) Uani 1 1 d . . . . .
H35 H 0.645279 0.554356 1.279190 0.025 Uiso 1 1 calc R U . . .
C36 C 0.7673(4) 0.5612(2) 1.4392(3) 0.0231(8) Uani 1 1 d . . . . .
H36 H 0.696983 0.543168 1.494440 0.028 Uiso 1 1 calc R U . . .
C37 C 0.9009(4) 0.5815(2) 1.4859(3) 0.0239(8) Uani 1 1 d . . . . .
H37 H 0.920698 0.579074 1.573178 0.029 Uiso 1 1 calc R U . . .
C38 C 1.0048(4) 0.6051(2) 1.4052(3) 0.0236(8) Uani 1 1 d . . . . .
H38 H 1.096676 0.617226 1.436931 0.028 Uiso 1 1 calc R U . . .
C39 C 0.9755(4) 0.6112(2) 1.2780(3) 0.0206(7) Uani 1 1 d . . . . .
H39 H 1.046536 0.627632 1.222443 0.025 Uiso 1 1 calc R U . . .
C27 C 0.8696(4) 0.3956(2) 1.0059(3) 0.0215(7) Uani 1 1 d . . . . .
C28 C 0.8839(4) 0.3171(2) 1.0759(3) 0.0183(7) Uani 1 1 d . . . . .
C29 C 0.8881(4) 0.3151(2) 1.2068(3) 0.0222(8) Uani 1 1 d . . . . .
H29 H 0.884324 0.365047 1.253123 0.027 Uiso 1 1 calc R U . . .
C30 C 0.8980(4) 0.2396(3) 1.2685(3) 0.0259(8) Uani 1 1 d . . . . .
H30 H 0.903173 0.238160 1.357141 0.031 Uiso 1 1 calc R U . . .
C31 C 0.9003(4) 0.1666(2) 1.2013(4) 0.0263(8) Uani 1 1 d . . . . .
H31 H 0.904767 0.115155 1.243888 0.032 Uiso 1 1 calc R U . . .
C32 C 0.8959(4) 0.1684(2) 1.0711(4) 0.0234(8) Uani 1 1 d . . . . .
H32 H 0.897926 0.118305 1.024886 0.028 Uiso 1 1 calc R U . . .
C33 C 0.8888(4) 0.2435(2) 1.0096(3) 0.0206(7) Uani 1 1 d . . . . .
H33 H 0.887131 0.244688 0.920946 0.025 Uiso 1 1 calc R U . . .


_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
Se1 C6 1.955(4) . ?
Se1 C2 1.915(3) . ?
Se21 C26 1.955(4) . ?
Se21 C22 1.928(3) . ?
F1 C20 1.350(4) . ?
F2 C20 1.333(4) . ?
F3 C20 1.349(4) . ?
F21 C40 1.332(4) . ?
F22 C40 1.340(4) . ?
F23 C40 1.353(4) . ?
O4 C4 1.206(4) . ?
O7 C7 1.220(4) . ?
O24 C24 1.208(4) . ?
O27 C27 1.225(4) . ?
N3 C4 1.412(4) . ?
N3 C2 1.391(4) . ?
N3 C14 1.465(4) . ?
N2 C2 1.290(5) . ?
N2 C7 1.398(4) . ?
N23 C24 1.415(5) . ?
N23 C22 1.378(4) . ?
N23 C34 1.463(4) . ?
N22 C22 1.292(5) . ?
N22 C27 1.394(5) . ?
C6 H6 1.0000 . ?
C6 C5 1.513(5) . ?
C6 C20 1.501(5) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C4 1.515(5) . ?
C14 C15 1.380(5) . ?
C14 C19 1.376(5) . ?
C15 H15 0.9500 . ?
C15 C16 1.395(5) . ?
C16 H16 0.9500 . ?
C16 C17 1.387(6) . ?
C17 H17 0.9500 . ?
C17 C18 1.387(5) . ?
C18 H18 0.9500 . ?
C18 C19 1.395(5) . ?
C19 H19 0.9500 . ?
C7 C8 1.480(5) . ?
C8 C9 1.397(5) . ?
C8 C13 1.399(5) . ?
C9 H9 0.9500 . ?
C9 C10 1.388(5) . ?
C10 H10 0.9500 . ?
C10 C11 1.390(6) . ?
C11 H11 0.9500 . ?
C11 C12 1.385(6) . ?
C12 H12 0.9500 . ?
C12 C13 1.375(6) . ?
C13 H13 0.9500 . ?
C26 H26 1.0000 . ?
C26 C25 1.514(5) . ?
C26 C40 1.508(5) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C25 C24 1.505(4) . ?
C34 C35 1.385(5) . ?
C34 C39 1.381(5) . ?
C35 H35 0.9500 . ?
C35 C36 1.394(5) . ?
C36 H36 0.9500 . ?
C36 C37 1.393(6) . ?
C37 H37 0.9500 . ?
C37 C38 1.384(5) . ?
C38 H38 0.9500 . ?
C38 C39 1.387(5) . ?
C39 H39 0.9500 . ?
C27 C28 1.480(5) . ?
C28 C29 1.402(5) . ?
C28 C33 1.388(5) . ?
C29 H29 0.9500 . ?
C29 C30 1.390(5) . ?
C30 H30 0.9500 . ?
C30 C31 1.384(6) . ?
C31 H31 0.9500 . ?
C31 C32 1.395(5) . ?
C32 H32 0.9500 . ?
C32 C33 1.382(5) . ?
C33 H33 0.9500 . ?

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
C2 Se1 C6 97.70(14) . . ?
C22 Se21 C26 97.77(14) . . ?
C4 N3 C14 114.8(3) . . ?
C2 N3 C4 128.2(3) . . ?
C2 N3 C14 117.0(3) . . ?
C2 N2 C7 118.9(3) . . ?
C24 N23 C34 114.6(3) . . ?
C22 N23 C24 128.5(3) . . ?
C22 N23 C34 117.0(3) . . ?
C22 N22 C27 119.2(3) . . ?
Se1 C6 H6 106.5 . . ?
C5 C6 Se1 109.9(2) . . ?
C5 C6 H6 106.5 . . ?
C20 C6 Se1 113.7(2) . . ?
C20 C6 H6 106.5 . . ?
C20 C6 C5 113.2(3) . . ?
C6 C5 H5A 108.5 . . ?
C6 C5 H5B 108.5 . . ?
C6 C5 C4 115.3(3) . . ?
H5A C5 H5B 107.5 . . ?
C4 C5 H5A 108.5 . . ?
C4 C5 H5B 108.5 . . ?
O4 C4 N3 118.6(3) . . ?
O4 C4 C5 121.2(3) . . ?
N3 C4 C5 120.2(3) . . ?
N3 C2 Se1 121.0(2) . . ?
N2 C2 Se1 121.8(3) . . ?
N2 C2 N3 117.2(3) . . ?
F1 C20 C6 113.1(3) . . ?
F2 C20 F1 107.0(3) . . ?
F2 C20 F3 107.1(3) . . ?
F2 C20 C6 113.1(3) . . ?
F3 C20 F1 106.2(3) . . ?
F3 C20 C6 110.1(3) . . ?
C15 C14 N3 118.4(3) . . ?
C19 C14 N3 119.5(3) . . ?
C19 C14 C15 122.1(3) . . ?
C14 C15 H15 120.6 . . ?
C14 C15 C16 118.8(3) . . ?
C16 C15 H15 120.6 . . ?
C15 C16 H16 120.0 . . ?
C17 C16 C15 119.9(3) . . ?
C17 C16 H16 120.0 . . ?
C16 C17 H17 119.8 . . ?
C16 C17 C18 120.5(3) . . ?
C18 C17 H17 119.8 . . ?
C17 C18 H18 120.1 . . ?
C17 C18 C19 119.7(3) . . ?
C19 C18 H18 120.1 . . ?
C14 C19 C18 119.0(3) . . ?
C14 C19 H19 120.5 . . ?
C18 C19 H19 120.5 . . ?
O7 C7 N2 122.7(3) . . ?
O7 C7 C8 122.0(3) . . ?
N2 C7 C8 115.2(3) . . ?
C9 C8 C7 121.9(3) . . ?
C9 C8 C13 119.8(3) . . ?
C13 C8 C7 118.3(3) . . ?
C8 C9 H9 120.3 . . ?
C10 C9 C8 119.4(3) . . ?
C10 C9 H9 120.3 . . ?
C9 C10 H10 119.8 . . ?
C9 C10 C11 120.4(3) . . ?
C11 C10 H10 119.8 . . ?
C10 C11 H11 120.1 . . ?
C12 C11 C10 119.9(4) . . ?
C12 C11 H11 120.1 . . ?
C11 C12 H12 119.8 . . ?
C13 C12 C11 120.4(4) . . ?
C13 C12 H12 119.8 . . ?
C8 C13 H13 120.0 . . ?
C12 C13 C8 120.1(3) . . ?
C12 C13 H13 120.0 . . ?
Se21 C26 H26 106.6 . . ?
C25 C26 Se21 110.1(2) . . ?
C25 C26 H26 106.6 . . ?
C40 C26 Se21 113.6(2) . . ?
C40 C26 H26 106.6 . . ?
C40 C26 C25 112.7(3) . . ?
C26 C25 H25A 108.5 . . ?
C26 C25 H25B 108.5 . . ?
H25A C25 H25B 107.5 . . ?
C24 C25 C26 114.9(3) . . ?
C24 C25 H25A 108.5 . . ?
C24 C25 H25B 108.5 . . ?
O24 C24 N23 118.9(3) . . ?
O24 C24 C25 121.0(3) . . ?
N23 C24 C25 120.1(3) . . ?
N23 C22 Se21 120.8(2) . . ?
N22 C22 Se21 122.0(3) . . ?
N22 C22 N23 117.1(3) . . ?
F21 C40 F22 107.3(3) . . ?
F21 C40 F23 106.3(3) . . ?
F21 C40 C26 113.8(3) . . ?
F22 C40 F23 106.0(3) . . ?
F22 C40 C26 110.4(3) . . ?
F23 C40 C26 112.6(3) . . ?
C35 C34 N23 118.3(3) . . ?
C39 C34 N23 119.9(3) . . ?
C39 C34 C35 121.8(3) . . ?
C34 C35 H35 120.7 . . ?
C34 C35 C36 118.6(3) . . ?
C36 C35 H35 120.7 . . ?
C35 C36 H36 119.9 . . ?
C37 C36 C35 120.2(4) . . ?
C37 C36 H36 119.9 . . ?
C36 C37 H37 120.0 . . ?
C38 C37 C36 120.0(3) . . ?
C38 C37 H37 120.0 . . ?
C37 C38 H38 119.9 . . ?
C37 C38 C39 120.3(3) . . ?
C39 C38 H38 119.9 . . ?
C34 C39 C38 119.1(3) . . ?
C34 C39 H39 120.4 . . ?
C38 C39 H39 120.4 . . ?
O27 C27 N22 123.2(3) . . ?
O27 C27 C28 120.6(3) . . ?
N22 C27 C28 116.3(3) . . ?
C29 C28 C27 121.8(3) . . ?
C33 C28 C27 118.7(3) . . ?
C33 C28 C29 119.4(3) . . ?
C28 C29 H29 120.1 . . ?
C30 C29 C28 119.8(4) . . ?
C30 C29 H29 120.1 . . ?
C29 C30 H30 119.9 . . ?
C31 C30 C29 120.2(3) . . ?
C31 C30 H30 119.9 . . ?
C30 C31 H31 119.9 . . ?
C30 C31 C32 120.2(3) . . ?
C32 C31 H31 119.9 . . ?
C31 C32 H32 120.2 . . ?
C33 C32 C31 119.6(3) . . ?
C33 C32 H32 120.2 . . ?
C28 C33 H33 119.6 . . ?
C32 C33 C28 120.8(3) . . ?
C32 C33 H33 119.6 . . ?

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
Se1 C6 C5 C4 -62.3(3) . . . . ?
Se1 C6 C20 F1 68.4(3) . . . . ?
Se1 C6 C20 F2 -53.4(3) . . . . ?
Se1 C6 C20 F3 -173.1(2) . . . . ?
Se21 C26 C25 C24 -62.7(3) . . . . ?
Se21 C26 C40 F21 -52.1(4) . . . . ?
Se21 C26 C40 F22 -172.8(2) . . . . ?
Se21 C26 C40 F23 68.9(3) . . . . ?
O7 C7 C8 C9 164.6(4) . . . . ?
O7 C7 C8 C13 -15.5(5) . . . . ?
O27 C27 C28 C29 -179.1(4) . . . . ?
O27 C27 C28 C33 -1.1(5) . . . . ?
N3 C14 C15 C16 -177.1(3) . . . . ?
N3 C14 C19 C18 176.8(3) . . . . ?
N2 C7 C8 C9 -14.1(5) . . . . ?
N2 C7 C8 C13 165.9(3) . . . . ?
N23 C34 C35 C36 -176.9(3) . . . . ?
N23 C34 C39 C38 176.6(3) . . . . ?
N22 C27 C28 C29 0.5(5) . . . . ?
N22 C27 C28 C33 178.5(3) . . . . ?
C6 C5 C4 O4 -142.5(3) . . . . ?
C6 C5 C4 N3 39.8(4) . . . . ?
C5 C6 C20 F1 -58.0(4) . . . . ?
C5 C6 C20 F2 -179.7(3) . . . . ?
C5 C6 C20 F3 60.6(4) . . . . ?
C4 N3 C2 Se1 -9.6(5) . . . . ?
C4 N3 C2 N2 172.2(3) . . . . ?
C4 N3 C14 C15 90.4(4) . . . . ?
C4 N3 C14 C19 -87.5(4) . . . . ?
C2 N3 C4 O4 -177.2(3) . . . . ?
C2 N3 C4 C5 0.6(5) . . . . ?
C2 N3 C14 C15 -90.0(4) . . . . ?
C2 N3 C14 C19 92.2(4) . . . . ?
C2 N2 C7 O7 31.3(5) . . . . ?
C2 N2 C7 C8 -150.1(3) . . . . ?
C20 C6 C5 C4 66.0(4) . . . . ?
C14 N3 C4 O4 2.5(5) . . . . ?
C14 N3 C4 C5 -179.8(3) . . . . ?
C14 N3 C2 Se1 170.8(2) . . . . ?
C14 N3 C2 N2 -7.5(4) . . . . ?
C14 C15 C16 C17 0.8(5) . . . . ?
C15 C14 C19 C18 -1.0(5) . . . . ?
C15 C16 C17 C18 -1.8(6) . . . . ?
C16 C17 C18 C19 1.5(6) . . . . ?
C17 C18 C19 C14 -0.1(5) . . . . ?
C19 C14 C15 C16 0.6(5) . . . . ?
C7 N2 C2 Se1 4.7(5) . . . . ?
C7 N2 C2 N3 -177.1(3) . . . . ?
C7 C8 C9 C10 -178.8(3) . . . . ?
C7 C8 C13 C12 -179.3(3) . . . . ?
C8 C9 C10 C11 -2.3(5) . . . . ?
C9 C8 C13 C12 0.7(5) . . . . ?
C9 C10 C11 C12 1.5(6) . . . . ?
C10 C11 C12 C13 0.5(6) . . . . ?
C11 C12 C13 C8 -1.5(5) . . . . ?
C13 C8 C9 C10 1.3(5) . . . . ?
C26 C25 C24 O24 -139.6(4) . . . . ?
C26 C25 C24 N23 42.5(5) . . . . ?
C25 C26 C40 F21 -178.2(3) . . . . ?
C25 C26 C40 F22 61.1(4) . . . . ?
C25 C26 C40 F23 -57.2(4) . . . . ?
C24 N23 C22 Se21 -10.7(5) . . . . ?
C24 N23 C22 N22 171.6(3) . . . . ?
C24 N23 C34 C35 95.7(4) . . . . ?
C24 N23 C34 C39 -82.2(4) . . . . ?
C22 N23 C24 O24 -179.3(3) . . . . ?
C22 N23 C24 C25 -1.3(5) . . . . ?
C22 N23 C34 C35 -83.8(4) . . . . ?
C22 N23 C34 C39 98.3(4) . . . . ?
C22 N22 C27 O27 19.2(6) . . . . ?
C22 N22 C27 C28 -160.4(3) . . . . ?
C40 C26 C25 C24 65.2(4) . . . . ?
C34 N23 C24 O24 1.2(5) . . . . ?
C34 N23 C24 C25 179.2(3) . . . . ?
C34 N23 C22 Se21 168.8(2) . . . . ?
C34 N23 C22 N22 -9.0(5) . . . . ?
C34 C35 C36 C37 0.7(5) . . . . ?
C35 C34 C39 C38 -1.2(5) . . . . ?
C35 C36 C37 C38 -2.2(6) . . . . ?
C36 C37 C38 C39 2.0(6) . . . . ?
C37 C38 C39 C34 -0.3(5) . . . . ?
C39 C34 C35 C36 1.0(5) . . . . ?
C27 N22 C22 Se21 3.3(5) . . . . ?
C27 N22 C22 N23 -179.0(3) . . . . ?
C27 C28 C29 C30 178.3(3) . . . . ?
C27 C28 C33 C32 -177.2(3) . . . . ?
C28 C29 C30 C31 -1.5(6) . . . . ?
C29 C28 C33 C32 0.8(5) . . . . ?
C29 C30 C31 C32 1.5(6) . . . . ?
C30 C31 C32 C33 -0.3(5) . . . . ?
C31 C32 C33 C28 -0.9(5) . . . . ?
C33 C28 C29 C30 0.4(5) . . . . ?

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Hexane into ethyl acetate'
