# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# 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_ld_1
_database_code_depnum_ccdc_archive 'CCDC 2389286'
loop_
_audit_author_name
_audit_author_address
'Haibo Mei'
;Nanjing Forestry University
China
;
_audit_update_record             
;
2024-10-08 deposited with the CCDC.	2024-12-04 downloaded from the CCDC.
;
_audit_creation_date             2024-07-07
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H21 F N2 O5 S'
_chemical_formula_sum            'C22 H21 F N2 O5 S'
_chemical_formula_weight         444.47
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O N S F'
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/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.0126(2)
_cell_length_b                   10.5943(2)
_cell_length_c                   19.0839(3)
_cell_angle_alpha                90
_cell_angle_beta                 95.7700(10)
_cell_angle_gamma                90
_cell_volume                     2014.10(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    10975
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.0580
_cell_measurement_theta_min      4.2250
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.852
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77472
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.92a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.466
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0245
_diffrn_reflns_av_unetI/netI     0.0204
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            15250
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.321
_diffrn_reflns_theta_min         4.658
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -15.00  11.00   0.50    0.10    --   45.87 -78.00  96.00   52
  2  ω     27.00 112.00   0.50    0.10    --   99.00 -78.00  96.00  170
  3  ω     29.00  73.00   0.50    0.10    --   99.00 -61.00  30.00   88
  4  ω     28.00  54.00   0.50    0.10    --   99.00 -61.00 120.00   52
  5  ω     29.00  65.00   0.50    0.10    --   99.00 -61.00   0.00   72
  6  ω     28.00  53.00   0.50    0.10    --   99.00 -45.00 -30.00   50
  7  ω     27.00  52.00   0.50    0.10    --   99.00 -45.00 -60.00   50
  8  ω    -22.00  28.00   0.50    0.10    --   45.87 -19.00  90.00  100
  9  ω     26.00 108.00   0.50    0.10    --   99.00 -77.00 -90.00  164
 10  ω     27.00  52.00   0.50    0.10    --   99.00 -45.00-120.00   50
 11  ω     27.00  52.00   0.50    0.10    --   99.00 -45.00-180.00   50
 12  ω    124.00 150.00   0.50    0.10    --   99.00  78.00-138.00   52
 13  ω    100.00 126.00   0.50    0.10    --   99.00 125.00 -60.00   52
 14  ω    135.00 161.00   0.50    0.10    --   99.00 125.00 -60.00   52
 15  ω     57.00 104.00   0.50    0.10    --   99.00 -94.00  30.00   94
 16  ω    -19.00  16.00   0.50    0.10    --  -45.87  37.00-180.00   70
 17  ω    -52.00  27.00   0.50    0.10    --  -45.87  78.00-138.00  158
 18  ω    -14.00  12.00   0.50    0.10    --  -45.87  19.00 -60.00   52
 19  ω    -40.00  26.00   0.50    0.10    --  -45.87  37.00 -30.00  132
 20  ω    -77.00 -27.00   0.50    0.10    --  -99.00  78.00-138.00  100
 21  ω    -68.00 -43.00   0.50    0.10    --  -99.00  61.00-150.00   50
 22  ω    -65.00 -31.00   0.50    0.10    --  -99.00  61.00-180.00   68
 23  ω    -68.00 -26.00   0.50    0.10    --  -99.00  61.00 -30.00   84
 24  ω   -175.00 -81.00   0.50    0.10    --  -99.00 -15.00 150.00  188
 25  ω   -174.00-137.00   0.50    0.10    --  -99.00 -30.00 120.00   74
 26  ω   -121.00 -95.00   0.50    0.10    --  -99.00 -30.00 120.00   52
 27  ω   -153.00 -97.00   0.50    0.10    --  -99.00 -78.00  96.00  112
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0909701000
_diffrn_orient_matrix_UB_12      -0.1137008000
_diffrn_orient_matrix_UB_13      0.0119096000
_diffrn_orient_matrix_UB_21      -0.1008120000
_diffrn_orient_matrix_UB_22      0.0444789000
_diffrn_orient_matrix_UB_23      -0.0613550000
_diffrn_orient_matrix_UB_31      0.0740747000
_diffrn_orient_matrix_UB_32      -0.0788843000
_diffrn_orient_matrix_UB_33      -0.0517614000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3675
_reflns_number_total             3937
_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 1.171.43.92a (Rigaku OD, 2023)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.92a 64-bit (release 05-10-2023))'
_computing_data_reduction        'CrysAlisPro 1.171.43.92a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.374
_refine_diff_density_min         -0.391
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       0.00090(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     285
_refine_ls_number_reflns         3937
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0331
_refine_ls_R_factor_gt           0.0309
_refine_ls_restrained_S_all      1.011
_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)+(0.0474P)²+0.8674P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0843
_refine_ls_wR_factor_ref         0.0860
_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 Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C16(H16), C17(H17), C19(H19), C20(H20)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C13(H13A,H13B,H13C), C21(H21A,H21B,H21C), C22(H22A,H22B,
 H22C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 0.72811(3) 0.58830(3) 0.65025(2) 0.01893(11) Uani 1 1 d . . . . .
F1 F 0.45452(10) 0.88075(9) 0.41957(4) 0.0365(2) Uani 1 1 d . . . . .
O1 O -0.01159(10) 0.79220(9) 0.50651(5) 0.0242(2) Uani 1 1 d . . . . .
O2 O 0.25164(10) 0.41575(9) 0.65461(5) 0.0276(2) Uani 1 1 d . . . . .
O3 O 0.63904(9) 0.42099(9) 0.79974(5) 0.0236(2) Uani 1 1 d . . . . .
O4 O 0.67193(10) 0.46280(9) 0.64483(5) 0.0240(2) Uani 1 1 d . . . . .
O5 O 0.86932(9) 0.60355(9) 0.64398(5) 0.0245(2) Uani 1 1 d . . . . .
N4 N 0.44065(11) 0.42009(10) 0.73183(6) 0.0193(2) Uani 1 1 d . . . . .
N9 N 0.43177(11) 0.80886(10) 0.70156(6) 0.0194(2) Uani 1 1 d . . . . .
C1 C 0.31741(13) 0.82064(13) 0.65367(7) 0.0193(3) Uani 1 1 d . . . . .
C2 C 0.25768(13) 0.92911(13) 0.62345(7) 0.0223(3) Uani 1 1 d . . . . .
H2 H 0.291625 1.010716 0.635811 0.027 Uiso 1 1 calc R U . . .
C3 C 0.14688(14) 0.91326(13) 0.57467(7) 0.0229(3) Uani 1 1 d . . . . .
H3 H 0.104153 0.985315 0.552916 0.027 Uiso 1 1 calc R U . . .
C4 C 0.09657(13) 0.79238(13) 0.55681(7) 0.0208(3) Uani 1 1 d . . . . .
C5 C 0.15279(13) 0.68452(12) 0.58850(7) 0.0200(3) Uani 1 1 d . . . . .
H5 H 0.116966 0.603253 0.576961 0.024 Uiso 1 1 calc R U . . .
C6 C 0.26470(13) 0.69988(12) 0.63830(7) 0.0187(3) Uani 1 1 d . . . . .
C7 C 0.34956(13) 0.61432(13) 0.68063(7) 0.0186(3) Uani 1 1 d . . . . .
C8 C 0.45012(13) 0.68416(12) 0.71689(7) 0.0180(3) Uani 1 1 d . . . . .
C9 C 0.56446(12) 0.62583(13) 0.76246(6) 0.0184(3) Uani 1 1 d . . . . .
C10 C 0.57121(14) 0.67289(14) 0.83967(7) 0.0242(3) Uani 1 1 d . . . . .
H10A H 0.638513 0.623870 0.868957 0.036 Uiso 1 1 calc R U . . .
H10B H 0.483264 0.662176 0.857257 0.036 Uiso 1 1 calc R U . . .
H10C H 0.596133 0.762371 0.841602 0.036 Uiso 1 1 calc R U . . .
C11 C 0.55039(12) 0.48057(13) 0.76574(6) 0.0191(3) Uani 1 1 d . . . . .
C12 C 0.34011(13) 0.47940(13) 0.68609(7) 0.0195(3) Uani 1 1 d . . . . .
C13 C 0.43969(14) 0.28196(13) 0.73507(7) 0.0237(3) Uani 1 1 d . . . . .
H13A H 0.496589 0.247857 0.700704 0.036 Uiso 1 1 calc R U . . .
H13B H 0.347637 0.251191 0.724200 0.036 Uiso 1 1 calc R U . . .
H13C H 0.474212 0.254405 0.782484 0.036 Uiso 1 1 calc R U . . .
C14 C 0.70207(13) 0.65192(12) 0.73486(6) 0.0191(3) Uani 1 1 d . . . . .
H14A H 0.773008 0.618127 0.769721 0.023 Uiso 1 1 calc R U . . .
H14B H 0.714664 0.744500 0.733016 0.023 Uiso 1 1 calc R U . . .
C15 C 0.63879(13) 0.68227(12) 0.58496(7) 0.0202(3) Uani 1 1 d . . . . .
C16 C 0.69225(14) 0.79825(13) 0.56748(7) 0.0233(3) Uani 1 1 d . . . . .
H16 H 0.771217 0.830022 0.593272 0.028 Uiso 1 1 calc R U . . .
C17 C 0.62841(15) 0.86643(14) 0.51189(7) 0.0269(3) Uani 1 1 d . . . . .
H17 H 0.661992 0.946151 0.499104 0.032 Uiso 1 1 calc R U . . .
C18 C 0.51457(15) 0.81557(14) 0.47547(7) 0.0263(3) Uani 1 1 d . . . . .
C19 C 0.45926(14) 0.70178(14) 0.49230(7) 0.0259(3) Uani 1 1 d . . . . .
H19 H 0.380135 0.670629 0.466377 0.031 Uiso 1 1 calc R U . . .
C20 C 0.52285(14) 0.63421(13) 0.54831(7) 0.0225(3) Uani 1 1 d . . . . .
H20 H 0.487390 0.555551 0.561551 0.027 Uiso 1 1 calc R U . . .
C21 C -0.05644(14) 0.67212(13) 0.47924(7) 0.0247(3) Uani 1 1 d . . . . .
H21A H -0.132014 0.684089 0.443058 0.037 Uiso 1 1 calc R U . . .
H21B H -0.085208 0.620201 0.517479 0.037 Uiso 1 1 calc R U . . .
H21C H 0.017177 0.629748 0.458478 0.037 Uiso 1 1 calc R U . . .
C22 C 0.50584(14) 0.91842(13) 0.73078(8) 0.0253(3) Uani 1 1 d . . . . .
H22A H 0.457555 0.956428 0.767691 0.038 Uiso 1 1 calc R U . . .
H22B H 0.514359 0.980433 0.693388 0.038 Uiso 1 1 calc R U . . .
H22C H 0.595397 0.892066 0.750918 0.038 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 O4 1.4434(10) . ?
S1 O5 1.4400(10) . ?
S1 C14 1.7929(13) . ?
S1 C15 1.7662(13) . ?
F1 C18 1.3593(16) . ?
O1 C4 1.3730(16) . ?
O1 C21 1.4297(17) . ?
O2 C12 1.2219(16) . ?
O3 C11 1.2212(16) . ?
N4 C11 1.3761(17) . ?
N4 C12 1.4119(16) . ?
N4 C13 1.4649(17) . ?
N9 C1 1.3970(16) . ?
N9 C8 1.3615(17) . ?
N9 C22 1.4578(17) . ?
C1 C2 1.3935(18) . ?
C1 C6 1.4036(18) . ?
C2 H2 0.9500 . ?
C2 C3 1.3848(19) . ?
C3 H3 0.9500 . ?
C3 C4 1.4056(19) . ?
C4 C5 1.3856(19) . ?
C5 H5 0.9500 . ?
C5 C6 1.4041(18) . ?
C6 C7 1.4346(18) . ?
C7 C8 1.3784(18) . ?
C7 C12 1.4369(19) . ?
C8 C9 1.4996(17) . ?
C9 C10 1.5506(17) . ?
C9 C11 1.5473(18) . ?
C9 C14 1.5486(17) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.3941(19) . ?
C15 C20 1.3902(19) . ?
C16 H16 0.9500 . ?
C16 C17 1.3854(19) . ?
C17 H17 0.9500 . ?
C17 C18 1.383(2) . ?
C18 C19 1.378(2) . ?
C19 H19 0.9500 . ?
C19 C20 1.3869(19) . ?
C20 H20 0.9500 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 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
O4 S1 C14 108.66(6) . . ?
O4 S1 C15 107.62(6) . . ?
O5 S1 O4 118.44(6) . . ?
O5 S1 C14 105.40(6) . . ?
O5 S1 C15 108.05(6) . . ?
C15 S1 C14 108.32(6) . . ?
C4 O1 C21 116.90(10) . . ?
C11 N4 C12 124.72(11) . . ?
C11 N4 C13 116.97(11) . . ?
C12 N4 C13 117.61(11) . . ?
C1 N9 C22 122.08(11) . . ?
C8 N9 C1 108.13(11) . . ?
C8 N9 C22 129.64(11) . . ?
N9 C1 C6 108.76(11) . . ?
C2 C1 N9 129.34(12) . . ?
C2 C1 C6 121.90(12) . . ?
C1 C2 H2 121.3 . . ?
C3 C2 C1 117.37(12) . . ?
C3 C2 H2 121.3 . . ?
C2 C3 H3 119.4 . . ?
C2 C3 C4 121.13(12) . . ?
C4 C3 H3 119.4 . . ?
O1 C4 C3 114.15(11) . . ?
O1 C4 C5 124.15(12) . . ?
C5 C4 C3 121.71(12) . . ?
C4 C5 H5 121.3 . . ?
C4 C5 C6 117.48(12) . . ?
C6 C5 H5 121.3 . . ?
C1 C6 C5 120.32(12) . . ?
C1 C6 C7 105.62(11) . . ?
C5 C6 C7 134.04(12) . . ?
C6 C7 C12 129.03(12) . . ?
C8 C7 C6 107.75(12) . . ?
C8 C7 C12 123.21(12) . . ?
N9 C8 C7 109.70(11) . . ?
N9 C8 C9 127.09(12) . . ?
C7 C8 C9 123.12(12) . . ?
C8 C9 C10 112.11(11) . . ?
C8 C9 C11 111.48(10) . . ?
C8 C9 C14 112.51(10) . . ?
C11 C9 C10 106.06(10) . . ?
C11 C9 C14 106.20(10) . . ?
C14 C9 C10 108.09(10) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O3 C11 N4 120.83(12) . . ?
O3 C11 C9 118.13(11) . . ?
N4 C11 C9 121.04(11) . . ?
O2 C12 N4 119.66(12) . . ?
O2 C12 C7 124.26(12) . . ?
N4 C12 C7 116.07(11) . . ?
N4 C13 H13A 109.5 . . ?
N4 C13 H13B 109.5 . . ?
N4 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
S1 C14 H14A 108.0 . . ?
S1 C14 H14B 108.0 . . ?
C9 C14 S1 117.01(9) . . ?
C9 C14 H14A 108.0 . . ?
C9 C14 H14B 108.0 . . ?
H14A C14 H14B 107.3 . . ?
C16 C15 S1 119.10(10) . . ?
C20 C15 S1 119.11(10) . . ?
C20 C15 C16 121.58(12) . . ?
C15 C16 H16 120.5 . . ?
C17 C16 C15 118.95(13) . . ?
C17 C16 H16 120.5 . . ?
C16 C17 H17 120.8 . . ?
C18 C17 C16 118.37(13) . . ?
C18 C17 H17 120.8 . . ?
F1 C18 C17 118.27(13) . . ?
F1 C18 C19 118.10(13) . . ?
C19 C18 C17 123.63(13) . . ?
C18 C19 H19 121.1 . . ?
C18 C19 C20 117.84(13) . . ?
C20 C19 H19 121.1 . . ?
C15 C20 H20 120.2 . . ?
C19 C20 C15 119.61(13) . . ?
C19 C20 H20 120.2 . . ?
O1 C21 H21A 109.5 . . ?
O1 C21 H21B 109.5 . . ?
O1 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N9 C22 H22A 109.5 . . ?
N9 C22 H22B 109.5 . . ?
N9 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 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
S1 C15 C16 C17 174.14(11) . . . . ?
S1 C15 C20 C19 -173.66(10) . . . . ?
F1 C18 C19 C20 178.45(12) . . . . ?
O1 C4 C5 C6 179.00(12) . . . . ?
O4 S1 C14 C9 -40.81(11) . . . . ?
O4 S1 C15 C16 -164.84(10) . . . . ?
O4 S1 C15 C20 9.89(12) . . . . ?
O5 S1 C14 C9 -168.71(9) . . . . ?
O5 S1 C15 C16 -35.86(12) . . . . ?
O5 S1 C15 C20 138.87(11) . . . . ?
N9 C1 C2 C3 177.25(13) . . . . ?
N9 C1 C6 C5 -176.77(11) . . . . ?
N9 C1 C6 C7 1.76(14) . . . . ?
N9 C8 C9 C10 62.36(17) . . . . ?
N9 C8 C9 C11 -178.90(12) . . . . ?
N9 C8 C9 C14 -59.72(17) . . . . ?
C1 N9 C8 C7 -0.59(15) . . . . ?
C1 N9 C8 C9 176.10(12) . . . . ?
C1 C2 C3 C4 0.3(2) . . . . ?
C1 C6 C7 C8 -2.11(14) . . . . ?
C1 C6 C7 C12 179.13(13) . . . . ?
C2 C1 C6 C5 3.4(2) . . . . ?
C2 C1 C6 C7 -178.07(12) . . . . ?
C2 C3 C4 O1 -178.54(12) . . . . ?
C2 C3 C4 C5 1.9(2) . . . . ?
C3 C4 C5 C6 -1.49(19) . . . . ?
C4 C5 C6 C1 -1.09(19) . . . . ?
C4 C5 C6 C7 -179.12(14) . . . . ?
C5 C6 C7 C8 176.13(14) . . . . ?
C5 C6 C7 C12 -2.6(2) . . . . ?
C6 C1 C2 C3 -3.0(2) . . . . ?
C6 C7 C8 N9 1.70(15) . . . . ?
C6 C7 C8 C9 -175.15(11) . . . . ?
C6 C7 C12 O2 -1.6(2) . . . . ?
C6 C7 C12 N4 178.99(12) . . . . ?
C7 C8 C9 C10 -121.36(14) . . . . ?
C7 C8 C9 C11 -2.62(17) . . . . ?
C7 C8 C9 C14 116.56(14) . . . . ?
C8 N9 C1 C2 179.04(13) . . . . ?
C8 N9 C1 C6 -0.78(15) . . . . ?
C8 C7 C12 O2 179.76(13) . . . . ?
C8 C7 C12 N4 0.40(19) . . . . ?
C8 C9 C11 O3 178.12(11) . . . . ?
C8 C9 C11 N4 -2.40(16) . . . . ?
C8 C9 C14 S1 -63.32(13) . . . . ?
C10 C9 C11 O3 -59.59(15) . . . . ?
C10 C9 C11 N4 119.90(12) . . . . ?
C10 C9 C14 S1 172.35(9) . . . . ?
C11 N4 C12 O2 174.81(12) . . . . ?
C11 N4 C12 C7 -5.79(18) . . . . ?
C11 C9 C14 S1 58.89(12) . . . . ?
C12 N4 C11 O3 -173.68(12) . . . . ?
C12 N4 C11 C9 6.85(19) . . . . ?
C12 C7 C8 N9 -179.44(12) . . . . ?
C12 C7 C8 C9 3.7(2) . . . . ?
C13 N4 C11 O3 -3.53(18) . . . . ?
C13 N4 C11 C9 177.00(11) . . . . ?
C13 N4 C12 O2 4.72(18) . . . . ?
C13 N4 C12 C7 -175.88(12) . . . . ?
C14 S1 C15 C16 77.86(12) . . . . ?
C14 S1 C15 C20 -107.42(11) . . . . ?
C14 C9 C11 O3 55.25(14) . . . . ?
C14 C9 C11 N4 -125.26(12) . . . . ?
C15 S1 C14 C9 75.83(11) . . . . ?
C15 C16 C17 C18 -0.7(2) . . . . ?
C16 C15 C20 C19 0.9(2) . . . . ?
C16 C17 C18 F1 -177.97(12) . . . . ?
C16 C17 C18 C19 1.4(2) . . . . ?
C17 C18 C19 C20 -0.9(2) . . . . ?
C18 C19 C20 C15 -0.3(2) . . . . ?
C20 C15 C16 C17 -0.4(2) . . . . ?
C21 O1 C4 C3 171.97(12) . . . . ?
C21 O1 C4 C5 -8.49(19) . . . . ?
C22 N9 C1 C2 3.0(2) . . . . ?
C22 N9 C1 C6 -176.78(12) . . . . ?
C22 N9 C8 C7 175.01(13) . . . . ?
C22 N9 C8 C9 -8.3(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 1.290
_oxdiff_exptl_absorpt_empirical_full_min 0.787
