# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_drh12-99-12
_database_code_depnum_ccdc_archive 'CCDC 2069936'
loop_
_audit_author_name
_audit_author_address
'Rui-Han Dai'
;University of Science and Technology of China
China
;
_audit_update_record             
;
2021-03-12 deposited with the CCDC.	2021-07-26 downloaded from the CCDC.
;
_audit_creation_date             2021-03-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C22 H22 F2 N2 O3 S'
_chemical_formula_sum            'C22 H22 F2 N2 O3 S'
_chemical_formula_weight         432.47
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         c20h20o2n2s2f3
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   10.36756(12)
_cell_length_b                   11.59613(14)
_cell_length_c                   17.36693(19)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2087.91(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6078
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      70.0620
_cell_measurement_theta_min      3.7860
_shelx_estimated_absorpt_T_max   0.765
_shelx_estimated_absorpt_T_min   0.697
_exptl_absorpt_coefficient_mu    1.766
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66550
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.16
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0190
_diffrn_reflns_av_unetI/netI     0.0224
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            7580
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.823
_diffrn_reflns_theta_min         4.585
_diffrn_ambient_temperature      291(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2169
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -63.00 -33.00   1.00    2.00    --  -40.80  38.00  30.00   30
  2  ω    -29.00  10.00   1.00    2.00    --  -40.80  38.00  30.00   39
  3  ω    -73.00  35.00   1.00    2.00    --  -40.80  77.00 -90.00  108
  4  ω    110.00 153.00   1.00    4.00    --   99.68 125.00   0.00   43
  5  ω     99.00 173.00   1.00    4.00    --   99.68 125.00 -60.00   74
  6  ω    107.00 167.00   1.00    4.00    --   99.68 125.00 150.00   60
  7  ω    100.00 138.00   1.00    4.00    --   99.68 125.00-180.00   38
  8  ω     80.00 173.00   1.00    4.00    --   99.68  45.00 120.00   93
  9  ω     19.00 100.00   1.00    4.00    --   99.68 -94.00  90.00   81
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0407299000
_diffrn_orient_matrix_UB_12      0.1120297000
_diffrn_orient_matrix_UB_13      -0.0410365000
_diffrn_orient_matrix_UB_21      0.1428356000
_diffrn_orient_matrix_UB_22      0.0300376000
_diffrn_orient_matrix_UB_23      -0.0139607000
_diffrn_orient_matrix_UB_31      -0.0042036000
_diffrn_orient_matrix_UB_32      -0.0647976000
_diffrn_orient_matrix_UB_33      -0.0773927000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.728
_reflns_Friedel_fraction_full    0.986
_reflns_Friedel_fraction_max     0.958
_reflns_number_gt                3768
_reflns_number_total             3856
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     64.99
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.252
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details 
;
 Flack x determined using 1562 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.027(7)
_refine_ls_extinction_coef       0.0031(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         3856
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0367
_refine_ls_R_factor_gt           0.0361
_refine_ls_restrained_S_all      1.091
_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)+(0.0609P)²+0.2791P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0996
_refine_ls_wR_factor_ref         0.1003
_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
 N1, C7
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
3.a Ternary CH refined with riding coordinates:
 C8(H8), C12(H12), C14(H14)
3.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C13(H13A,H13B), C9(H9A,H9B)
3.c Aromatic/amide H refined with riding coordinates:
 C18(H18), C22(H22), C20(H20), C5(H5), C2(H2), C10(H10), C4(H4), C3(H3)
3.d X=CH2 refined with riding coordinates:
 C11(H11A,H11B)
3.e Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.39047(6) 0.78817(5) 0.49433(3) 0.04258(19) Uani 1 1 d . . . . .
O2 O 0.5208(2) 0.82531(19) 0.50776(13) 0.0573(5) Uani 1 1 d . . . . .
F2 F 0.6134(2) 0.40902(19) 0.43535(14) 0.0790(6) Uani 1 1 d . . . . .
N2 N 0.3815(2) 0.84588(19) 0.76594(12) 0.0396(5) Uani 1 1 d . . . . .
F1 F 0.2076(2) 0.4737(2) 0.32545(13) 0.0780(6) Uani 1 1 d . . . . .
O3 O 0.3085(2) 0.85857(18) 0.44712(12) 0.0563(5) Uani 1 1 d . . . . .
N1 N 0.6910(2) 0.74951(19) 0.76864(13) 0.0430(5) Uani 1 1 d . U . . .
O1 O 0.6550(2) 0.8944(2) 0.85049(14) 0.0612(6) Uani 1 1 d . . . . .
C8 C 0.4667(2) 0.7745(2) 0.81366(14) 0.0422(6) Uani 1 1 d . . . . .
H8 H 0.4602 0.6957 0.7937 0.051 Uiso 1 1 calc R . . . .
C7 C 0.6068(3) 0.8066(2) 0.81006(15) 0.0465(6) Uani 1 1 d . U . . .
C15 C 0.3074(3) 0.8834(2) 0.62987(16) 0.0457(6) Uani 1 1 d . . . . .
H15A H 0.3354 0.9502 0.6007 0.055 Uiso 1 1 calc R . . . .
H15B H 0.2253 0.8979 0.6548 0.055 Uiso 1 1 calc R . . . .
C12 C 0.4111(2) 0.8350(2) 0.68413(14) 0.0390(5) Uani 1 1 d . . . . .
H12 H 0.4965 0.8664 0.6721 0.047 Uiso 1 1 calc R . . . .
C18 C 0.2939(3) 0.6143(3) 0.40737(16) 0.0483(6) Uani 1 1 d . . . . .
H18 H 0.2214 0.6605 0.4010 0.058 Uiso 1 1 calc R . . . .
C1 C 0.7855(3) 0.8941(3) 0.83357(19) 0.0540(7) Uani 1 1 d . . . . .
C6 C 0.8087(3) 0.8046(2) 0.78353(17) 0.0481(6) Uani 1 1 d . . . . .
C13 C 0.3923(3) 0.7138(2) 0.64865(14) 0.0463(6) Uani 1 1 d . . . . .
H13A H 0.3438 0.6613 0.6811 0.056 Uiso 1 1 calc R . . . .
H13B H 0.4717 0.6785 0.6309 0.056 Uiso 1 1 calc R . . . .
C19 C 0.3045(3) 0.5077(3) 0.37200(17) 0.0550(7) Uani 1 1 d . . . . .
C17 C 0.3971(3) 0.6485(2) 0.45287(14) 0.0433(6) Uani 1 1 d . . . . .
C21 C 0.5077(3) 0.4762(3) 0.42704(19) 0.0555(7) Uani 1 1 d . . . . .
C14 C 0.3113(3) 0.7694(2) 0.58354(15) 0.0424(6) Uani 1 1 d . . . . .
H14 H 0.2260 0.7339 0.5780 0.051 Uiso 1 1 calc R . . . .
C22 C 0.5050(3) 0.5811(3) 0.46434(17) 0.0489(6) Uani 1 1 d . . . . .
H22 H 0.5726 0.6052 0.4957 0.059 Uiso 1 1 calc R . . . .
C20 C 0.4088(4) 0.4374(3) 0.38040(18) 0.0587(8) Uani 1 1 d . . . . .
H20 H 0.4132 0.3662 0.3558 0.070 Uiso 1 1 calc R . . . .
C16 C 0.3781(3) 0.9683(2) 0.78731(19) 0.0555(7) Uani 1 1 d . . . . .
H16A H 0.3518 0.9756 0.8401 0.083 Uiso 1 1 calc GR . . . .
H16B H 0.3179 1.0082 0.7548 0.083 Uiso 1 1 calc GR . . . .
H16C H 0.4625 1.0012 0.7810 0.083 Uiso 1 1 calc GR . . . .
C5 C 0.9315(3) 0.7810(4) 0.7571(2) 0.0649(9) Uani 1 1 d . . . . .
H5 H 0.9483 0.7209 0.7231 0.078 Uiso 1 1 calc R . . . .
C9 C 0.4227(3) 0.7697(3) 0.89795(17) 0.0623(8) Uani 1 1 d . . . . .
H9A H 0.4414 0.8428 0.9227 0.075 Uiso 1 1 calc R . . . .
H9B H 0.3302 0.7576 0.8998 0.075 Uiso 1 1 calc R . . . .
C2 C 0.8829(4) 0.9658(3) 0.8603(3) 0.0775(11) Uani 1 1 d . . . . .
H2 H 0.8663 1.0262 0.8941 0.093 Uiso 1 1 calc R . . . .
C10 C 0.4905(5) 0.6727(4) 0.9415(2) 0.0833(12) Uani 1 1 d . . . . .
H10 H 0.4536 0.5999 0.9370 0.100 Uiso 1 1 calc R . . . .
C4 C 1.0283(3) 0.8529(4) 0.7846(3) 0.0792(13) Uani 1 1 d . . . . .
H4 H 1.1127 0.8397 0.7687 0.095 Uiso 1 1 calc R . . . .
C3 C 1.0044(4) 0.9429(4) 0.8342(3) 0.0820(12) Uani 1 1 d . . . . .
H3 H 1.0725 0.9892 0.8504 0.098 Uiso 1 1 calc R . . . .
C11 C 0.5898(6) 0.6788(5) 0.9829(3) 0.1040(16) Uani 1 1 d . . . . .
H11A H 0.6312 0.7492 0.9897 0.125 Uiso 1 1 calc R . . . .
H11B H 0.6219 0.6128 1.0066 0.125 Uiso 1 1 calc R . . . .


_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 O2 1.437(2) . ?
S1 O3 1.436(2) . ?
S1 C17 1.773(3) . ?
S1 C14 1.767(3) . ?
F2 C21 1.352(4) . ?
N2 C8 1.468(3) . ?
N2 C12 1.459(3) . ?
N2 C16 1.468(3) . ?
F1 C19 1.349(4) . ?
N1 C7 1.311(4) . ?
N1 C6 1.401(3) . ?
O1 C7 1.334(3) . ?
O1 C1 1.384(4) . ?
C8 H8 0.9800 . ?
C8 C7 1.500(4) . ?
C8 C9 1.534(4) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C12 1.536(3) . ?
C15 C14 1.548(4) . ?
C12 H12 0.9800 . ?
C12 C13 1.547(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.384(5) . ?
C18 C17 1.388(4) . ?
C1 C6 1.375(5) . ?
C1 C2 1.388(5) . ?
C6 C5 1.381(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.549(3) . ?
C19 C20 1.362(5) . ?
C17 C22 1.380(4) . ?
C21 C22 1.378(5) . ?
C21 C20 1.382(5) . ?
C14 H14 0.9800 . ?
C22 H22 0.9300 . ?
C20 H20 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C5 H5 0.9300 . ?
C5 C4 1.389(6) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.527(6) . ?
C2 H2 0.9300 . ?
C2 C3 1.364(7) . ?
C10 H10 0.9300 . ?
C10 C11 1.257(7) . ?
C4 H4 0.9300 . ?
C4 C3 1.376(7) . ?
C3 H3 0.9300 . ?
C11 H11A 0.9300 . ?
C11 H11B 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 S1 C17 107.65(13) . . ?
O2 S1 C14 109.35(13) . . ?
O3 S1 O2 118.61(14) . . ?
O3 S1 C17 108.07(13) . . ?
O3 S1 C14 107.22(13) . . ?
C14 S1 C17 105.15(12) . . ?
C8 N2 C16 114.7(2) . . ?
C12 N2 C8 112.0(2) . . ?
C12 N2 C16 109.6(2) . . ?
C7 N1 C6 104.4(2) . . ?
C7 O1 C1 104.6(2) . . ?
N2 C8 H8 106.5 . . ?
N2 C8 C7 114.8(2) . . ?
N2 C8 C9 112.3(2) . . ?
C7 C8 H8 106.5 . . ?
C7 C8 C9 109.7(2) . . ?
C9 C8 H8 106.5 . . ?
N1 C7 O1 115.1(2) . . ?
N1 C7 C8 122.9(2) . . ?
O1 C7 C8 122.0(3) . . ?
H15A C15 H15B 111.0 . . ?
C12 C15 H15A 113.8 . . ?
C12 C15 H15B 113.8 . . ?
C12 C15 C14 89.34(19) . . ?
C14 C15 H15A 113.8 . . ?
C14 C15 H15B 113.8 . . ?
N2 C12 C15 114.8(2) . . ?
N2 C12 H12 111.5 . . ?
N2 C12 C13 116.1(2) . . ?
C15 C12 H12 111.5 . . ?
C15 C12 C13 89.98(19) . . ?
C13 C12 H12 111.5 . . ?
C19 C18 H18 121.7 . . ?
C19 C18 C17 116.5(3) . . ?
C17 C18 H18 121.7 . . ?
O1 C1 C2 129.7(3) . . ?
C6 C1 O1 107.9(2) . . ?
C6 C1 C2 122.4(3) . . ?
C1 C6 N1 108.0(2) . . ?
C1 C6 C5 121.4(3) . . ?
C5 C6 N1 130.6(3) . . ?
C12 C13 H13A 113.8 . . ?
C12 C13 H13B 113.8 . . ?
C12 C13 C14 88.91(19) . . ?
H13A C13 H13B 111.1 . . ?
C14 C13 H13A 113.8 . . ?
C14 C13 H13B 113.8 . . ?
F1 C19 C18 117.9(3) . . ?
F1 C19 C20 118.7(3) . . ?
C20 C19 C18 123.4(3) . . ?
C18 C17 S1 117.6(2) . . ?
C22 C17 S1 119.4(2) . . ?
C22 C17 C18 123.0(3) . . ?
F2 C21 C22 118.4(3) . . ?
F2 C21 C20 118.4(3) . . ?
C22 C21 C20 123.2(3) . . ?
S1 C14 H14 112.7 . . ?
C15 C14 S1 111.25(19) . . ?
C15 C14 C13 89.43(19) . . ?
C15 C14 H14 112.7 . . ?
C13 C14 S1 116.08(19) . . ?
C13 C14 H14 112.7 . . ?
C17 C22 H22 121.7 . . ?
C21 C22 C17 116.7(3) . . ?
C21 C22 H22 121.7 . . ?
C19 C20 C21 117.2(3) . . ?
C19 C20 H20 121.4 . . ?
C21 C20 H20 121.4 . . ?
N2 C16 H16A 109.5 . . ?
N2 C16 H16B 109.5 . . ?
N2 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C6 C5 H5 122.2 . . ?
C6 C5 C4 115.7(4) . . ?
C4 C5 H5 122.2 . . ?
C8 C9 H9A 109.4 . . ?
C8 C9 H9B 109.4 . . ?
H9A C9 H9B 108.0 . . ?
C10 C9 C8 111.3(3) . . ?
C10 C9 H9A 109.4 . . ?
C10 C9 H9B 109.4 . . ?
C1 C2 H2 121.8 . . ?
C3 C2 C1 116.4(4) . . ?
C3 C2 H2 121.8 . . ?
C9 C10 H10 115.9 . . ?
C11 C10 C9 128.2(5) . . ?
C11 C10 H10 115.9 . . ?
C5 C4 H4 118.6 . . ?
C3 C4 C5 122.7(4) . . ?
C3 C4 H4 118.6 . . ?
C2 C3 C4 121.4(4) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
C10 C11 H11A 120.0 . . ?
C10 C11 H11B 120.0 . . ?
H11A C11 H11B 120.0 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.470
_oxdiff_exptl_absorpt_empirical_full_min 0.661
####################################################################### 
# 
# 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_drh12-99-11
_database_code_depnum_ccdc_archive 'CCDC 2069934'
loop_
_audit_author_name
_audit_author_address
'Rui-Han Dai'
;University of Science and Technology of China
China
;
_audit_update_record             
;
2021-03-12 deposited with the CCDC.	2021-07-26 downloaded from the CCDC.
;
_audit_creation_date             2021-03-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C22 H22 F2 N2 O3 S'
_chemical_formula_sum            'C22 H22 F2 N2 O3 S'
_chemical_formula_weight         432.47
_chemical_melting_point          ?
_chemical_oxdiff_formula         c20h20o2n2s2f3
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.21316(16)
_cell_length_b                   17.3615(2)
_cell_length_c                   10.31999(14)
_cell_angle_alpha                90
_cell_angle_beta                 98.3484(13)
_cell_angle_gamma                90
_cell_volume                     2165.05(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5232
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      69.7900
_cell_measurement_theta_min      5.0980
_shelx_estimated_absorpt_T_max   0.772
_shelx_estimated_absorpt_T_min   0.716
_exptl_absorpt_coefficient_mu    1.703
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69084
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.16
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0168
_diffrn_reflns_av_unetI/netI     0.0183
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            8742
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.890
_diffrn_reflns_theta_min         3.658
_diffrn_ambient_temperature      291(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2169
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -82.00 -34.00   1.00    2.00    --  -40.80 178.00   0.00   48
  2  ω   -110.00 -85.00   1.00    2.00    --  -40.80 -38.00 -30.00   25
  3  ω    -53.00  34.00   1.00    2.00    --  -40.80  77.00 -90.00   87
  4  ω    -70.00 -19.00   1.00    2.00    --  -40.80 -38.00 -30.00   51
  5  ω     72.00 175.00   1.00    4.00    --   99.68  30.00   0.00  103
  6  ω     26.00 118.00   1.00    4.00    --   99.68-125.00  90.00   92
  7  ω     66.00  93.00   1.00    4.00    --   99.68 -94.00 -90.00   27
  8  ω     75.00 163.00   1.00    4.00    --   99.68  45.00 -90.00   88
  9  ω     42.00 129.00   1.00    4.00    --   99.68 -61.00-180.00   87
 10  ω     47.00  88.00   1.00    4.00    --   99.68 -45.00  60.00   41
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0972056000
_diffrn_orient_matrix_UB_12      -0.0487528000
_diffrn_orient_matrix_UB_13      0.0677472000
_diffrn_orient_matrix_UB_21      0.0742503000
_diffrn_orient_matrix_UB_22      0.0720558000
_diffrn_orient_matrix_UB_23      0.0134289000
_diffrn_orient_matrix_UB_31      -0.0357840000
_diffrn_orient_matrix_UB_32      0.0174217000
_diffrn_orient_matrix_UB_33      0.1342003000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3546
_reflns_number_total             4001
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     64.99
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.343
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       0.0012(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         4001
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0515
_refine_ls_R_factor_gt           0.0468
_refine_ls_restrained_S_all      1.032
_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)+(0.0713P)²+0.6822P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1295
_refine_ls_wR_factor_ref         0.1348
_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
 N1, C7
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
3.a Ternary CH refined with riding coordinates:
 C12(H12), C8(H8), C14(H14)
3.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C15(H15A,H15B), C9(H9A,H9B)
3.c Aromatic/amide H refined with riding coordinates:
 C18(H18), C10(H10), C5(H5), C20(H20), C22(H22), C2(H2), C4(H4), C3(H3)
3.d X=CH2 refined with riding coordinates:
 C11(H11A,H11B)
3.e Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.64477(4) 0.27583(3) 0.19646(5) 0.06057(19) Uani 1 1 d . . . . .
O1 O 0.39965(12) 0.45394(8) 0.60897(14) 0.0626(4) Uani 1 1 d . . . . .
N2 N 0.31129(12) 0.38747(9) 0.29577(14) 0.0476(4) Uani 1 1 d . . . . .
N1 N 0.22431(13) 0.41445(11) 0.56505(14) 0.0565(4) Uani 1 1 d . U . . .
O2 O 0.61756(14) 0.33117(11) 0.09359(14) 0.0780(5) Uani 1 1 d . . . . .
O3 O 0.65612(15) 0.19657(11) 0.16069(18) 0.0880(6) Uani 1 1 d . . . . .
F1 F 0.94546(15) 0.47142(11) 0.3386(3) 0.1345(8) Uani 1 1 d . . . . .
C12 C 0.39879(15) 0.33378(10) 0.34430(17) 0.0486(4) Uani 1 1 d . . . . .
H12 H 0.3847 0.3107 0.4270 0.058 Uiso 1 1 calc R . . . .
C8 C 0.31612(16) 0.45730(11) 0.37738(17) 0.0497(4) Uani 1 1 d . . . . .
H8 H 0.3880 0.4815 0.3730 0.060 Uiso 1 1 calc R . . . .
C7 C 0.31118(16) 0.44129(11) 0.51914(18) 0.0518(4) Uani 1 1 d . U . . .
C13 C 0.51943(15) 0.36160(11) 0.35570(18) 0.0507(4) Uani 1 1 d . . . . .
H13A H 0.5308 0.4032 0.2964 0.061 Uiso 1 1 calc R . . . .
H13B H 0.5533 0.3730 0.4445 0.061 Uiso 1 1 calc R . . . .
C14 C 0.54789(17) 0.28152(11) 0.30705(18) 0.0520(4) Uani 1 1 d . . . . .
H14 H 0.5682 0.2464 0.3810 0.062 Uiso 1 1 calc R . . . .
C15 C 0.42511(17) 0.27092(11) 0.2486(2) 0.0552(5) Uani 1 1 d . . . . .
H15A H 0.4080 0.2852 0.1571 0.066 Uiso 1 1 calc R . . . .
H15B H 0.3952 0.2207 0.2648 0.066 Uiso 1 1 calc R . . . .
C6 C 0.25769(18) 0.40977(12) 0.70056(18) 0.0582(5) Uani 1 1 d . . . . .
C1 C 0.36475(18) 0.43444(11) 0.72618(19) 0.0567(5) Uani 1 1 d . . . . .
C9 C 0.22757(18) 0.51690(12) 0.3270(2) 0.0596(5) Uani 1 1 d . . . . .
H9A H 0.1559 0.4975 0.3418 0.071 Uiso 1 1 calc R . . . .
H9B H 0.2419 0.5637 0.3779 0.071 Uiso 1 1 calc R . . . .
F2 F 0.9690(2) 0.23515(16) 0.5535(3) 0.1712(13) Uani 1 1 d . . . . .
C16 C 0.20477(17) 0.34768(13) 0.2768(2) 0.0617(5) Uani 1 1 d . . . . .
H16A H 0.2072 0.3059 0.2163 0.093 Uiso 1 1 calc GR . . . .
H16B H 0.1475 0.3831 0.2424 0.093 Uiso 1 1 calc GR . . . .
H16C H 0.1896 0.3279 0.3592 0.093 Uiso 1 1 calc GR . . . .
C17 C 0.76868(17) 0.30612(13) 0.2930(2) 0.0594(5) Uani 1 1 d . . . . .
C18 C 0.80805(18) 0.37952(14) 0.2767(2) 0.0694(6) Uani 1 1 d . . . . .
H18 H 0.7712 0.4131 0.2150 0.083 Uiso 1 1 calc R . . . .
C19 C 0.90330(19) 0.40091(16) 0.3547(3) 0.0800(7) Uani 1 1 d . . . . .
C10 C 0.2223(2) 0.53618(14) 0.1858(2) 0.0766(7) Uani 1 1 d . . . . .
H10 H 0.2889 0.5459 0.1550 0.092 Uiso 1 1 calc R . . . .
C5 C 0.2007(2) 0.38559(18) 0.7987(2) 0.0859(8) Uani 1 1 d . . . . .
H5 H 0.1280 0.3681 0.7822 0.103 Uiso 1 1 calc R . . . .
C20 C 0.9591(2) 0.35439(18) 0.4473(3) 0.0855(8) Uani 1 1 d . . . . .
H20 H 1.0238 0.3705 0.4989 0.103 Uiso 1 1 calc R . . . .
C22 C 0.8213(2) 0.25624(17) 0.3862(3) 0.0875(8) Uani 1 1 d . . . . .
H22 H 0.7940 0.2071 0.3974 0.105 Uiso 1 1 calc R . . . .
C2 C 0.4224(3) 0.43655(15) 0.8523(3) 0.0896(9) Uani 1 1 d . . . . .
H2 H 0.4956 0.4529 0.8691 0.108 Uiso 1 1 calc R . . . .
C4 C 0.2600(4) 0.38916(19) 0.9250(3) 0.1009(11) Uani 1 1 d . . . . .
H4 H 0.2250 0.3742 0.9952 0.121 Uiso 1 1 calc R . . . .
C3 C 0.3667(4) 0.41366(17) 0.9494(3) 0.1014(11) Uani 1 1 d . . . . .
H3 H 0.4024 0.4147 1.0354 0.122 Uiso 1 1 calc R . . . .
C21 C 0.9159(2) 0.28265(19) 0.4616(3) 0.0971(9) Uani 1 1 d . . . . .
C11 C 0.1320(3) 0.54053(19) 0.1016(3) 0.1066(10) Uani 1 1 d . . . . .
H11A H 0.0637 0.5312 0.1284 0.128 Uiso 1 1 calc R . . . .
H11B H 0.1358 0.5530 0.0147 0.128 Uiso 1 1 calc R . . . .


_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 O2 1.4346(17) . ?
S1 O3 1.4365(18) . ?
S1 C14 1.762(2) . ?
S1 C17 1.767(2) . ?
O1 C7 1.336(2) . ?
O1 C1 1.382(3) . ?
N2 C12 1.451(2) . ?
N2 C8 1.472(2) . ?
N2 C16 1.461(2) . ?
N1 C7 1.309(3) . ?
N1 C6 1.401(2) . ?
F1 C19 1.348(3) . ?
C12 H12 0.9800 . ?
C12 C13 1.539(3) . ?
C12 C15 1.536(3) . ?
C8 H8 0.9800 . ?
C8 C7 1.499(3) . ?
C8 C9 1.532(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.535(3) . ?
C14 H14 0.9800 . ?
C14 C15 1.544(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C6 C1 1.365(3) . ?
C6 C5 1.375(3) . ?
C1 C2 1.388(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.488(3) . ?
F2 C21 1.350(3) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C18 1.381(3) . ?
C17 C22 1.382(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.366(4) . ?
C19 C20 1.357(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.303(4) . ?
C5 H5 0.9300 . ?
C5 C4 1.398(4) . ?
C20 H20 0.9300 . ?
C20 C21 1.369(4) . ?
C22 H22 0.9300 . ?
C22 C21 1.374(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.349(5) . ?
C4 H4 0.9300 . ?
C4 C3 1.360(5) . ?
C3 H3 0.9300 . ?
C11 H11A 0.9300 . ?
C11 H11B 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 S1 O3 118.16(11) . . ?
O2 S1 C14 109.67(9) . . ?
O2 S1 C17 107.77(11) . . ?
O3 S1 C14 108.61(11) . . ?
O3 S1 C17 108.86(10) . . ?
C14 S1 C17 102.65(9) . . ?
C7 O1 C1 104.24(16) . . ?
C12 N2 C8 111.41(14) . . ?
C12 N2 C16 109.83(15) . . ?
C16 N2 C8 115.27(15) . . ?
C7 N1 C6 104.37(16) . . ?
N2 C12 H12 110.4 . . ?
N2 C12 C13 118.27(15) . . ?
N2 C12 C15 116.53(15) . . ?
C13 C12 H12 110.4 . . ?
C15 C12 H12 110.4 . . ?
C15 C12 C13 89.13(14) . . ?
N2 C8 H8 106.7 . . ?
N2 C8 C7 113.68(15) . . ?
N2 C8 C9 113.22(15) . . ?
C7 C8 H8 106.7 . . ?
C7 C8 C9 109.26(16) . . ?
C9 C8 H8 106.7 . . ?
O1 C7 C8 120.24(17) . . ?
N1 C7 O1 115.08(16) . . ?
N1 C7 C8 124.68(17) . . ?
C12 C13 H13A 114.1 . . ?
C12 C13 H13B 114.1 . . ?
H13A C13 H13B 111.3 . . ?
C14 C13 C12 87.16(14) . . ?
C14 C13 H13A 114.1 . . ?
C14 C13 H13B 114.1 . . ?
S1 C14 H14 110.6 . . ?
C13 C14 S1 117.89(14) . . ?
C13 C14 H14 110.6 . . ?
C13 C14 C15 88.99(14) . . ?
C15 C14 S1 116.49(14) . . ?
C15 C14 H14 110.6 . . ?
C12 C15 C14 86.93(14) . . ?
C12 C15 H15A 114.2 . . ?
C12 C15 H15B 114.2 . . ?
C14 C15 H15A 114.2 . . ?
C14 C15 H15B 114.2 . . ?
H15A C15 H15B 111.3 . . ?
C1 C6 N1 107.88(17) . . ?
C1 C6 C5 121.8(2) . . ?
C5 C6 N1 130.4(2) . . ?
O1 C1 C2 129.5(2) . . ?
C6 C1 O1 108.42(16) . . ?
C6 C1 C2 122.1(2) . . ?
C8 C9 H9A 108.7 . . ?
C8 C9 H9B 108.7 . . ?
H9A C9 H9B 107.6 . . ?
C10 C9 C8 114.34(18) . . ?
C10 C9 H9A 108.7 . . ?
C10 C9 H9B 108.7 . . ?
N2 C16 H16A 109.5 . . ?
N2 C16 H16B 109.5 . . ?
N2 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 S1 119.41(17) . . ?
C18 C17 C22 121.9(2) . . ?
C22 C17 S1 118.68(19) . . ?
C17 C18 H18 121.3 . . ?
C19 C18 C17 117.4(2) . . ?
C19 C18 H18 121.3 . . ?
F1 C19 C18 118.8(3) . . ?
F1 C19 C20 117.8(2) . . ?
C20 C19 C18 123.4(3) . . ?
C9 C10 H10 117.3 . . ?
C11 C10 C9 125.3(3) . . ?
C11 C10 H10 117.3 . . ?
C6 C5 H5 122.5 . . ?
C6 C5 C4 115.1(3) . . ?
C4 C5 H5 122.5 . . ?
C19 C20 H20 121.4 . . ?
C19 C20 C21 117.1(2) . . ?
C21 C20 H20 121.4 . . ?
C17 C22 H22 121.5 . . ?
C21 C22 C17 116.9(3) . . ?
C21 C22 H22 121.5 . . ?
C1 C2 H2 121.7 . . ?
C3 C2 C1 116.6(3) . . ?
C3 C2 H2 121.7 . . ?
C5 C4 H4 118.7 . . ?
C3 C4 C5 122.7(3) . . ?
C3 C4 H4 118.7 . . ?
C2 C3 C4 121.8(3) . . ?
C2 C3 H3 119.1 . . ?
C4 C3 H3 119.1 . . ?
F2 C21 C20 118.6(3) . . ?
F2 C21 C22 118.2(3) . . ?
C20 C21 C22 123.2(3) . . ?
C10 C11 H11A 120.0 . . ?
C10 C11 H11B 120.0 . . ?
H11A C11 H11B 120.0 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.317
_oxdiff_exptl_absorpt_empirical_full_min 0.773
