# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2023

####################################################################### 
# 
# 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_hsap_2
_database_code_depnum_ccdc_archive 'CCDC 2183275'
loop_
_audit_author_name
_audit_author_address
zxy
;Nanjing Forestry University
China
;
_audit_update_record             
;
2022-07-01 deposited with the CCDC.	2023-06-21 downloaded from the CCDC.
;
_audit_creation_date             2021-07-20
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2020.09.11 svn.r3730fd0d for OlexSys, GUI svn.r6159)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H30 F N O2 S'
_chemical_formula_sum            'C24 H30 F N O2 S'
_chemical_formula_weight         415.55
_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 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.0575(6)
_cell_length_b                   10.2338(8)
_cell_length_c                   13.7884(9)
_cell_angle_alpha                85.464(6)
_cell_angle_beta                 88.881(5)
_cell_angle_gamma                84.269(6)
_cell_volume                     1127.67(14)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3548
_cell_measurement_temperature    150.1(4)
_cell_measurement_theta_max      28.8770
_cell_measurement_theta_min      2.5480
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.171
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78444
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.224
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             444
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0252
_diffrn_reflns_av_unetI/netI     0.0430
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8377
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.006
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.1(4)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -18.00  53.00   1.00    3.50    --   11.90 -99.00   0.00   71
  2  ω    -15.00  27.00   1.00    3.50    --  -11.27 -99.00-150.00   42
  3  ω    -74.00  10.00   1.00    3.50    --  -11.27 -37.00  30.00   84
  4  ω    -29.00  41.00   1.00    3.50    --  -11.27  57.00-180.00   70
  5  ω      1.00  57.00   1.00    3.50    --  -11.27  57.00-150.00   56
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0444828000
_diffrn_orient_matrix_UB_12      -0.0557744000
_diffrn_orient_matrix_UB_13      0.0112873000
_diffrn_orient_matrix_UB_21      -0.0037054000
_diffrn_orient_matrix_UB_22      0.0136797000
_diffrn_orient_matrix_UB_23      0.0496721000
_diffrn_orient_matrix_UB_31      -0.0763929000
_diffrn_orient_matrix_UB_32      0.0397950000
_diffrn_orient_matrix_UB_33      -0.0082804000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3292
_reflns_number_total             3978
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         1.106
_refine_diff_density_min         -1.035
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     261
_refine_ls_number_reflns         3978
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0654
_refine_ls_R_factor_gt           0.0544
_refine_ls_restrained_S_all      1.052
_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)+(0.0481P)²+1.2519P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1243
_refine_ls_wR_factor_ref         0.1326
_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. Rigid bond restraints
 S1, O2
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
O2 \\sim S1: within 2A with sigma of 0.002 and sigma for terminal atoms of
0.004 within 2A
Uanis(S1) = Uanis(O2)
4.a Ternary CH refined with riding coordinates:
 C11(H11)
4.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C12(H12A,H12B)
4.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C8(H8), C15(H15), C16(H16), C17(H17),
 C18(H18), C19(H19)
4.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C23(H23A,H23B,
 H23C), C24(H24A,H24B,H24C)
;
_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 0.34724(8) 0.16908(6) 0.99617(4) 0.02349(18) Uani 1 1 d . U . . .
F1 F 0.21294(18) 0.27840(16) 0.96558(13) 0.0405(4) Uani 1 1 d . . . . .
O1 O 0.3275(2) 0.05844(16) 0.94381(12) 0.0255(4) Uani 1 1 d . . . . .
O2 O 0.3366(2) 0.14994(16) 1.10074(12) 0.02349(18) Uani 1 1 d . U . . .
N1 N 0.4604(2) 0.35495(18) 0.80748(14) 0.0171(4) Uani 1 1 d . . . . .
C1 C 0.2206(3) 0.2870(3) 0.54576(18) 0.0242(6) Uani 1 1 d . . . . .
C2 C 0.2979(3) 0.4008(2) 0.55459(18) 0.0243(6) Uani 1 1 d . . . . .
H2 H 0.296783 0.463595 0.501989 0.029 Uiso 1 1 calc R U . . .
C3 C 0.3766(3) 0.4238(2) 0.63904(17) 0.0216(5) Uani 1 1 d . . . . .
H3 H 0.428714 0.500502 0.641516 0.026 Uiso 1 1 calc R U . . .
C4 C 0.3788(3) 0.3340(2) 0.72019(17) 0.0172(5) Uani 1 1 d . . . . .
C5 C 0.2984(3) 0.2205(2) 0.71343(17) 0.0203(5) Uani 1 1 d . . . . .
H5 H 0.295204 0.159617 0.767013 0.024 Uiso 1 1 calc R U . . .
C6 C 0.2235(3) 0.1978(2) 0.62787(18) 0.0236(6) Uani 1 1 d . . . . .
H6 H 0.173127 0.120347 0.624893 0.028 Uiso 1 1 calc R U . . .
C7 C 0.5078(3) 0.4819(2) 0.82175(16) 0.0181(5) Uani 1 1 d . . . . .
C8 C 0.6601(3) 0.4982(2) 0.85200(17) 0.0207(5) Uani 1 1 d . . . . .
H8 H 0.681342 0.582732 0.865040 0.025 Uiso 1 1 calc R U . . .
C9 C 0.7996(3) 0.3904(2) 0.86654(19) 0.0231(6) Uani 1 1 d . . . . .
H9A H 0.824894 0.376094 0.935286 0.028 Uiso 1 1 calc R U . . .
H9B H 0.898602 0.417469 0.832588 0.028 Uiso 1 1 calc R U . . .
C10 C 0.7562(3) 0.2610(2) 0.82932(18) 0.0209(5) Uani 1 1 d . . . . .
C11 C 0.5709(3) 0.2453(2) 0.85440(17) 0.0185(5) Uani 1 1 d . . . . .
H11 H 0.543086 0.163337 0.829276 0.022 Uiso 1 1 calc R U . . .
C12 C 0.5355(3) 0.2367(2) 0.96429(17) 0.0194(5) Uani 1 1 d . . . . .
H12A H 0.530842 0.324383 0.986993 0.023 Uiso 1 1 calc R U . . .
H12B H 0.626802 0.183129 0.997137 0.023 Uiso 1 1 calc R U . . .
C13 C 0.8701(3) 0.1444(3) 0.8747(2) 0.0280(6) Uani 1 1 d . . . . .
H13A H 0.864594 0.144594 0.944309 0.042 Uiso 1 1 calc R U . . .
H13B H 0.982782 0.151855 0.852777 0.042 Uiso 1 1 calc R U . . .
H13C H 0.834195 0.063684 0.855502 0.042 Uiso 1 1 calc R U . . .
C14 C 0.3742(3) 0.5933(2) 0.81424(17) 0.0203(5) Uani 1 1 d . . . . .
C15 C 0.4108(3) 0.7180(2) 0.77790(19) 0.0274(6) Uani 1 1 d . . . . .
H15 H 0.516590 0.729776 0.752605 0.033 Uiso 1 1 calc R U . . .
C16 C 0.2907(4) 0.8248(3) 0.7791(2) 0.0362(7) Uani 1 1 d . . . . .
H16 H 0.316598 0.907841 0.754886 0.043 Uiso 1 1 calc R U . . .
C17 C 0.1335(4) 0.8086(3) 0.8160(2) 0.0387(8) Uani 1 1 d . . . . .
H17 H 0.053651 0.880681 0.817592 0.046 Uiso 1 1 calc R U . . .
C18 C 0.0950(3) 0.6850(3) 0.8505(2) 0.0337(7) Uani 1 1 d . . . . .
H18 H -0.011400 0.673645 0.875029 0.040 Uiso 1 1 calc R U . . .
C19 C 0.2139(3) 0.5776(3) 0.84894(18) 0.0247(6) Uani 1 1 d . . . . .
H19 H 0.186176 0.494296 0.871283 0.030 Uiso 1 1 calc R U . . .
C20 C 0.1390(4) 0.2567(3) 0.45157(19) 0.0318(6) Uani 1 1 d . . . . .
C21 C -0.0410(4) 0.2250(4) 0.4721(2) 0.0468(8) Uani 1 1 d . . . . .
H21A H -0.041108 0.150103 0.518688 0.070 Uiso 1 1 calc R U . . .
H21B H -0.090562 0.205566 0.412838 0.070 Uiso 1 1 calc R U . . .
H21C H -0.104069 0.299444 0.497748 0.070 Uiso 1 1 calc R U . . .
C22 C 0.1351(4) 0.3726(3) 0.3747(2) 0.0440(8) Uani 1 1 d . . . . .
H22A H 0.075616 0.448798 0.400056 0.066 Uiso 1 1 calc R U . . .
H22B H 0.079960 0.351116 0.317802 0.066 Uiso 1 1 calc R U . . .
H22C H 0.247061 0.390806 0.357917 0.066 Uiso 1 1 calc R U . . .
C23 C 0.2390(4) 0.1368(3) 0.4113(2) 0.0482(8) Uani 1 1 d . . . . .
H23A H 0.352525 0.155198 0.399813 0.072 Uiso 1 1 calc R U . . .
H23B H 0.190892 0.118309 0.351333 0.072 Uiso 1 1 calc R U . . .
H23C H 0.236045 0.061847 0.457587 0.072 Uiso 1 1 calc R U . . .
C24 C 0.7782(3) 0.2657(3) 0.71867(19) 0.0279(6) Uani 1 1 d . . . . .
H24A H 0.739625 0.188434 0.695102 0.042 Uiso 1 1 calc R U . . .
H24B H 0.893959 0.269040 0.701955 0.042 Uiso 1 1 calc R U . . .
H24C H 0.714626 0.342727 0.689527 0.042 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
S1 F1 1.5172(16) . ?
S1 O1 1.4135(18) . ?
S1 O2 1.4418(18) . ?
S1 C12 1.763(2) . ?
N1 C4 1.423(3) . ?
N1 C7 1.420(3) . ?
N1 C11 1.476(3) . ?
C1 C2 1.389(3) . ?
C1 C6 1.396(3) . ?
C1 C20 1.534(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.384(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.390(3) . ?
C4 C5 1.396(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.382(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.334(3) . ?
C7 C14 1.487(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.499(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.531(3) . ?
C10 C11 1.547(3) . ?
C10 C13 1.530(3) . ?
C10 C24 1.530(3) . ?
C11 H11 0.9800 . ?
C11 C12 1.534(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.390(3) . ?
C14 C19 1.389(4) . ?
C15 H15 0.9300 . ?
C15 C16 1.387(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.377(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.379(4) . ?
C18 H18 0.9300 . ?
C18 C19 1.386(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.534(4) . ?
C20 C22 1.525(4) . ?
C20 C23 1.535(4) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?

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
F1 S1 C12 104.10(10) . . ?
O1 S1 F1 108.91(10) . . ?
O1 S1 O2 116.65(10) . . ?
O1 S1 C12 111.43(11) . . ?
O2 S1 F1 106.42(10) . . ?
O2 S1 C12 108.48(11) . . ?
C4 N1 C11 118.50(18) . . ?
C7 N1 C4 119.59(18) . . ?
C7 N1 C11 114.23(18) . . ?
C2 C1 C6 116.2(2) . . ?
C2 C1 C20 123.1(2) . . ?
C6 C1 C20 120.7(2) . . ?
C1 C2 H2 118.9 . . ?
C3 C2 C1 122.2(2) . . ?
C3 C2 H2 118.9 . . ?
C2 C3 H3 119.5 . . ?
C2 C3 C4 121.0(2) . . ?
C4 C3 H3 119.5 . . ?
C3 C4 N1 122.0(2) . . ?
C3 C4 C5 117.6(2) . . ?
C5 C4 N1 120.4(2) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 C4 120.6(2) . . ?
C6 C5 H5 119.7 . . ?
C1 C6 H6 118.8 . . ?
C5 C6 C1 122.4(2) . . ?
C5 C6 H6 118.8 . . ?
N1 C7 C14 116.91(19) . . ?
C8 C7 N1 121.4(2) . . ?
C8 C7 C14 121.2(2) . . ?
C7 C8 H8 117.6 . . ?
C7 C8 C9 124.8(2) . . ?
C9 C8 H8 117.6 . . ?
C8 C9 H9A 109.2 . . ?
C8 C9 H9B 109.2 . . ?
C8 C9 C10 112.16(19) . . ?
H9A C9 H9B 107.9 . . ?
C10 C9 H9A 109.2 . . ?
C10 C9 H9B 109.2 . . ?
C9 C10 C11 108.29(19) . . ?
C13 C10 C9 110.7(2) . . ?
C13 C10 C11 111.05(19) . . ?
C24 C10 C9 109.9(2) . . ?
C24 C10 C11 108.28(19) . . ?
C24 C10 C13 108.6(2) . . ?
N1 C11 C10 111.16(18) . . ?
N1 C11 H11 108.0 . . ?
N1 C11 C12 108.87(19) . . ?
C10 C11 H11 108.0 . . ?
C12 C11 C10 112.66(19) . . ?
C12 C11 H11 108.0 . . ?
S1 C12 H12A 109.0 . . ?
S1 C12 H12B 109.0 . . ?
C11 C12 S1 113.06(16) . . ?
C11 C12 H12A 109.0 . . ?
C11 C12 H12B 109.0 . . ?
H12A C12 H12B 107.8 . . ?
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 . . ?
C15 C14 C7 120.2(2) . . ?
C19 C14 C7 121.0(2) . . ?
C19 C14 C15 118.7(2) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 C14 120.5(3) . . ?
C16 C15 H15 119.8 . . ?
C15 C16 H16 119.8 . . ?
C17 C16 C15 120.4(3) . . ?
C17 C16 H16 119.8 . . ?
C16 C17 H17 120.2 . . ?
C16 C17 C18 119.6(2) . . ?
C18 C17 H17 120.2 . . ?
C17 C18 H18 119.8 . . ?
C17 C18 C19 120.4(3) . . ?
C19 C18 H18 119.8 . . ?
C14 C19 H19 119.8 . . ?
C18 C19 C14 120.5(3) . . ?
C18 C19 H19 119.8 . . ?
C1 C20 C21 110.2(2) . . ?
C1 C20 C23 108.7(2) . . ?
C21 C20 C23 109.0(3) . . ?
C22 C20 C1 111.9(2) . . ?
C22 C20 C21 108.1(2) . . ?
C22 C20 C23 108.9(2) . . ?
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 . . ?
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 . . ?
C20 C23 H23A 109.5 . . ?
C20 C23 H23B 109.5 . . ?
C20 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C10 C24 H24A 109.5 . . ?
C10 C24 H24B 109.5 . . ?
C10 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 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
F1 S1 C12 C11 -74.21(19) . . . . ?
O1 S1 C12 C11 43.0(2) . . . . ?
O2 S1 C12 C11 172.75(16) . . . . ?
N1 C4 C5 C6 -178.0(2) . . . . ?
N1 C7 C8 C9 5.0(4) . . . . ?
N1 C7 C14 C15 -146.9(2) . . . . ?
N1 C7 C14 C19 37.3(3) . . . . ?
N1 C11 C12 S1 74.7(2) . . . . ?
C1 C2 C3 C4 -1.2(4) . . . . ?
C2 C1 C6 C5 0.1(4) . . . . ?
C2 C1 C20 C21 -127.1(3) . . . . ?
C2 C1 C20 C22 -6.9(4) . . . . ?
C2 C1 C20 C23 113.4(3) . . . . ?
C2 C3 C4 N1 179.3(2) . . . . ?
C2 C3 C4 C5 -0.3(4) . . . . ?
C3 C4 C5 C6 1.6(3) . . . . ?
C4 N1 C7 C8 -132.4(2) . . . . ?
C4 N1 C7 C14 55.5(3) . . . . ?
C4 N1 C11 C10 99.7(2) . . . . ?
C4 N1 C11 C12 -135.7(2) . . . . ?
C4 C5 C6 C1 -1.6(4) . . . . ?
C6 C1 C2 C3 1.3(4) . . . . ?
C6 C1 C20 C21 54.2(3) . . . . ?
C6 C1 C20 C22 174.5(3) . . . . ?
C6 C1 C20 C23 -65.2(3) . . . . ?
C7 N1 C4 C3 14.8(3) . . . . ?
C7 N1 C4 C5 -165.6(2) . . . . ?
C7 N1 C11 C10 -49.7(3) . . . . ?
C7 N1 C11 C12 74.9(2) . . . . ?
C7 C8 C9 C10 7.9(3) . . . . ?
C7 C14 C15 C16 -174.0(2) . . . . ?
C7 C14 C19 C18 173.5(2) . . . . ?
C8 C7 C14 C15 41.0(3) . . . . ?
C8 C7 C14 C19 -134.8(3) . . . . ?
C8 C9 C10 C11 -38.8(3) . . . . ?
C8 C9 C10 C13 -160.7(2) . . . . ?
C8 C9 C10 C24 79.4(2) . . . . ?
C9 C10 C11 N1 60.6(2) . . . . ?
C9 C10 C11 C12 -62.0(2) . . . . ?
C10 C11 C12 S1 -161.48(16) . . . . ?
C11 N1 C4 C3 -133.0(2) . . . . ?
C11 N1 C4 C5 46.7(3) . . . . ?
C11 N1 C7 C8 16.7(3) . . . . ?
C11 N1 C7 C14 -155.5(2) . . . . ?
C13 C10 C11 N1 -177.73(19) . . . . ?
C13 C10 C11 C12 59.8(3) . . . . ?
C14 C7 C8 C9 176.8(2) . . . . ?
C14 C15 C16 C17 -0.3(4) . . . . ?
C15 C14 C19 C18 -2.4(4) . . . . ?
C15 C16 C17 C18 -0.9(4) . . . . ?
C16 C17 C18 C19 0.5(4) . . . . ?
C17 C18 C19 C14 1.2(4) . . . . ?
C19 C14 C15 C16 1.9(4) . . . . ?
C20 C1 C2 C3 -177.4(2) . . . . ?
C20 C1 C6 C5 178.8(2) . . . . ?
C24 C10 C11 N1 -58.6(2) . . . . ?
C24 C10 C11 C12 178.9(2) . . . . ?

_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 1.482
_oxdiff_exptl_absorpt_empirical_full_min 0.513
