# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_1_a
_database_code_depnum_ccdc_archive 'CCDC 2087188'
loop_
_audit_author_name
_audit_author_address
'yabo deng'
;lanzhou university
China
;
_audit_update_record             
;
2021-06-01 deposited with the CCDC.	2021-11-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H20 F2 N2 O4 S'
_chemical_formula_weight         458.47

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'
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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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'

_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.
;

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                   11.8735(14)
_cell_length_b                   12.1602(14)
_cell_length_c                   15.2898(18)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2207.6(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4867
_cell_measurement_theta_min      2.17
_cell_measurement_theta_max      21.91

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_F_000             952
_exptl_transmission_factor_min   0.6778
_exptl_transmission_factor_max   0.7458
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.196
_shelx_estimated_absorpt_T_min   0.944
_shelx_estimated_absorpt_T_max   0.962
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX II area detector'
_diffrn_measurement_method       'ω scan'
_diffrn_detector_area_resol_mean 'fine-focus sealed tube'
_diffrn_reflns_number            18498
_diffrn_reflns_av_unetI/netI     0.0323
_diffrn_reflns_av_R_equivalents  0.0285
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.140
_diffrn_reflns_theta_max         29.130
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.924
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5495
_reflns_number_gt                3800
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.728
_reflns_Friedel_fraction_max     0.887
_reflns_Friedel_fraction_full    0.999

_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.
;

_computing_data_collection       'Bruker SMART APEX II'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0200P)²+0.5410P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1309 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(3)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         5495
_refine_ls_number_parameters     291
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0698
_refine_ls_R_factor_gt           0.0430
_refine_ls_wR_factor_ref         0.0857
_refine_ls_wR_factor_gt          0.0774
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_restrained_S_all      0.999
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
C1 C 0.7900(3) 0.7858(3) 0.7875(2) 0.0702(9) Uani 1 1 d . . . . .
C2 C 0.8818(4) 0.7352(4) 0.8281(3) 0.0960(12) Uani 1 1 d . . . . .
H2 H 0.8719 0.6731 0.8628 0.115 Uiso 1 1 calc R U . . .
C3 C 0.9876(4) 0.7796(5) 0.8157(3) 0.1193(17) Uani 1 1 d . . . . .
H3 H 1.0501 0.7472 0.8418 0.143 Uiso 1 1 calc R U . . .
C4 C 1.0004(4) 0.8725(5) 0.7642(3) 0.1123(16) Uani 1 1 d . . . . .
H4 H 1.0723 0.9008 0.7557 0.135 Uiso 1 1 calc R U . . .
C5 C 0.9110(4) 0.9242(4) 0.7252(3) 0.0904(12) Uani 1 1 d . . . . .
H5 H 0.9210 0.9879 0.6924 0.109 Uiso 1 1 calc R U . . .
C6 C 0.8050(3) 0.8781(3) 0.7365(2) 0.0701(9) Uani 1 1 d . . . . .
C7 C 0.6734(3) 0.7541(2) 0.7987(2) 0.0645(8) Uani 1 1 d . . . . .
C8 C 0.5911(3) 0.8291(2) 0.74578(18) 0.0555(7) Uani 1 1 d . . . . .
C9 C 0.4207(2) 0.7242(2) 0.74049(18) 0.0542(7) Uani 1 1 d . . . . .
H9 H 0.4474 0.6587 0.7715 0.065 Uiso 1 1 calc R U . . .
C10 C 0.4065(3) 0.8179(2) 0.8074(2) 0.0609(7) Uani 1 1 d . . . . .
H10 H 0.3446 0.8662 0.7894 0.073 Uiso 1 1 calc R U . . .
C11 C 0.5164(2) 0.76555(19) 0.67984(17) 0.0503(6) Uani 1 1 d . . . . .
C12 C 0.4747(2) 0.8359(2) 0.60515(18) 0.0511(7) Uani 1 1 d . . . . .
C13 C 0.4177(3) 0.9350(2) 0.6033(2) 0.0582(7) Uani 1 1 d . . . . .
H13 H 0.3993 0.9711 0.6550 0.070 Uiso 1 1 calc R U . . .
C14 C 0.3882(3) 0.9798(3) 0.5228(2) 0.0700(9) Uani 1 1 d . . . . .
H14 H 0.3512 1.0471 0.5204 0.084 Uiso 1 1 calc R U . . .
C15 C 0.4137(3) 0.9248(3) 0.4466(2) 0.0777(10) Uani 1 1 d . . . . .
H15 H 0.3910 0.9547 0.3935 0.093 Uiso 1 1 calc R U . . .
C16 C 0.4721(3) 0.8262(3) 0.4468(2) 0.0715(9) Uani 1 1 d . . . . .
H16 H 0.4899 0.7898 0.3951 0.086 Uiso 1 1 calc R U . . .
C17 C 0.5027(2) 0.7844(2) 0.52729(18) 0.0561(7) Uani 1 1 d . . . . .
C18 C 0.5751(2) 0.6707(2) 0.63175(19) 0.0541(7) Uani 1 1 d . . . . .
C19 C 0.2496(3) 0.5782(3) 0.5771(3) 0.0935(12) Uani 1 1 d . . . . .
H19A H 0.2271 0.6379 0.5388 0.112 Uiso 1 1 calc R U . . .
H19B H 0.1849 0.5566 0.6118 0.112 Uiso 1 1 calc R U . . .
C20 C 0.2890(5) 0.4855(3) 0.5255(3) 0.127(2) Uani 1 1 d . . . . .
H20A H 0.3499 0.5087 0.4886 0.191 Uiso 1 1 calc R U . . .
H20B H 0.2284 0.4583 0.4900 0.191 Uiso 1 1 calc R U . . .
H20C H 0.3146 0.4282 0.5639 0.191 Uiso 1 1 calc R U . . .
C21 C 0.3832(4) 0.7722(3) 0.8974(2) 0.0868(12) Uani 1 1 d . . . . .
H21 H 0.4452 0.7249 0.9166 0.104 Uiso 1 1 calc R U . . .
C22 C 0.3166(3) 0.6942(2) 0.6900(2) 0.0632(7) Uani 1 1 d . . . . .
C23 C 0.6042(3) 0.6112(3) 0.4787(2) 0.0830(11) Uani 1 1 d . . . . .
H23A H 0.6492 0.5553 0.5060 0.125 Uiso 1 1 calc R U . . .
H23B H 0.6487 0.6496 0.4361 0.125 Uiso 1 1 calc R U . . .
H23C H 0.5407 0.5778 0.4504 0.125 Uiso 1 1 calc R U . . .
F1 F 0.3670(3) 0.85461(18) 0.95444(15) 0.1415(12) Uani 1 1 d . . . . .
F2 F 0.2841(2) 0.7143(2) 0.89520(16) 0.1246(9) Uani 1 1 d . . . . .
N1 N 0.5118(2) 0.87830(18) 0.80596(16) 0.0637(7) Uani 1 1 d . . . . .
H1 H 0.5253 0.9359 0.8369 0.076 Uiso 1 1 calc R U . . .
N2 N 0.5649(2) 0.68836(19) 0.54465(16) 0.0604(6) Uani 1 1 d . . . . .
O1 O 0.62085(19) 0.59227(16) 0.66574(14) 0.0698(6) Uani 1 1 d . . . . .
O2 O 0.2262(2) 0.7363(2) 0.69757(18) 0.0929(8) Uani 1 1 d . . . . .
O3 O 0.34020(19) 0.61424(16) 0.63398(14) 0.0668(6) Uani 1 1 d . . . . .
O4 O 0.6374(2) 0.68431(19) 0.84741(15) 0.0862(7) Uani 1 1 d . . . . .
S1 S 0.68003(8) 0.93026(6) 0.69058(6) 0.0687(2) Uani 1 1 d . . . . .


_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
C1 C6 1.379(5) . ?
C1 C2 1.397(5) . ?
C1 C7 1.447(5) . ?
C2 C3 1.380(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.386(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.369(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.389(5) . ?
C5 H5 0.9300 . ?
C6 S1 1.760(4) . ?
C7 O4 1.207(4) . ?
C7 C8 1.562(4) . ?
C8 N1 1.446(4) . ?
C8 C11 1.549(4) . ?
C8 S1 1.828(3) . ?
C9 C22 1.502(4) . ?
C9 C10 1.540(4) . ?
C9 C11 1.550(4) . ?
C9 H9 0.9800 . ?
C10 N1 1.450(4) . ?
C10 C21 1.511(4) . ?
C10 H10 0.9800 . ?
C11 C12 1.511(4) . ?
C11 C18 1.535(4) . ?
C12 C13 1.382(4) . ?
C12 C17 1.386(4) . ?
C13 C14 1.390(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.376(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.385(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.381(4) . ?
C16 H16 0.9300 . ?
C17 N2 1.406(4) . ?
C18 O1 1.215(3) . ?
C18 N2 1.354(4) . ?
C19 O3 1.451(4) . ?
C19 C20 1.453(5) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 F1 1.342(4) . ?
C21 F2 1.371(5) . ?
C21 H21 0.9800 . ?
C22 O2 1.195(4) . ?
C22 O3 1.326(4) . ?
C23 N2 1.455(4) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
N1 H1 0.8600 . ?

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
C6 C1 C2 120.6(4) . . ?
C6 C1 C7 114.0(3) . . ?
C2 C1 C7 125.2(4) . . ?
C3 C2 C1 118.5(5) . . ?
C3 C2 H2 120.8 . . ?
C1 C2 H2 120.8 . . ?
C2 C3 C4 119.8(5) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C5 C4 C3 122.5(5) . . ?
C5 C4 H4 118.8 . . ?
C3 C4 H4 118.8 . . ?
C4 C5 C6 117.5(5) . . ?
C4 C5 H5 121.2 . . ?
C6 C5 H5 121.2 . . ?
C1 C6 C5 121.1(4) . . ?
C1 C6 S1 114.2(3) . . ?
C5 C6 S1 124.7(3) . . ?
O4 C7 C1 126.7(3) . . ?
O4 C7 C8 120.6(3) . . ?
C1 C7 C8 112.5(3) . . ?
N1 C8 C11 104.3(2) . . ?
N1 C8 C7 108.6(2) . . ?
C11 C8 C7 113.8(2) . . ?
N1 C8 S1 113.02(18) . . ?
C11 C8 S1 111.46(19) . . ?
C7 C8 S1 105.7(2) . . ?
C22 C9 C10 115.5(3) . . ?
C22 C9 C11 112.0(2) . . ?
C10 C9 C11 103.8(2) . . ?
C22 C9 H9 108.4 . . ?
C10 C9 H9 108.4 . . ?
C11 C9 H9 108.4 . . ?
N1 C10 C21 111.0(3) . . ?
N1 C10 C9 105.7(2) . . ?
C21 C10 C9 110.7(2) . . ?
N1 C10 H10 109.8 . . ?
C21 C10 H10 109.8 . . ?
C9 C10 H10 109.8 . . ?
C12 C11 C18 102.3(2) . . ?
C12 C11 C8 113.4(2) . . ?
C18 C11 C8 115.2(2) . . ?
C12 C11 C9 113.3(2) . . ?
C18 C11 C9 112.1(2) . . ?
C8 C11 C9 101.1(2) . . ?
C13 C12 C17 119.6(3) . . ?
C13 C12 C11 132.1(3) . . ?
C17 C12 C11 108.3(2) . . ?
C12 C13 C14 118.9(3) . . ?
C12 C13 H13 120.6 . . ?
C14 C13 H13 120.6 . . ?
C15 C14 C13 120.2(3) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C14 C15 C16 121.9(3) . . ?
C14 C15 H15 119.0 . . ?
C16 C15 H15 119.0 . . ?
C17 C16 C15 116.9(3) . . ?
C17 C16 H16 121.6 . . ?
C15 C16 H16 121.6 . . ?
C16 C17 C12 122.4(3) . . ?
C16 C17 N2 127.7(3) . . ?
C12 C17 N2 109.9(2) . . ?
O1 C18 N2 125.8(3) . . ?
O1 C18 C11 126.0(3) . . ?
N2 C18 C11 108.1(2) . . ?
O3 C19 C20 108.7(3) . . ?
O3 C19 H19A 109.9 . . ?
C20 C19 H19A 109.9 . . ?
O3 C19 H19B 109.9 . . ?
C20 C19 H19B 109.9 . . ?
H19A C19 H19B 108.3 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
F1 C21 F2 106.0(3) . . ?
F1 C21 C10 110.1(3) . . ?
F2 C21 C10 108.9(3) . . ?
F1 C21 H21 110.6 . . ?
F2 C21 H21 110.6 . . ?
C10 C21 H21 110.6 . . ?
O2 C22 O3 124.5(3) . . ?
O2 C22 C9 125.9(3) . . ?
O3 C22 C9 109.6(3) . . ?
N2 C23 H23A 109.5 . . ?
N2 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
N2 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C8 N1 C10 111.2(2) . . ?
C8 N1 H1 124.4 . . ?
C10 N1 H1 124.4 . . ?
C18 N2 C17 111.4(2) . . ?
C18 N2 C23 123.4(3) . . ?
C17 N2 C23 125.0(3) . . ?
C22 O3 C19 116.9(3) . . ?
C6 S1 C8 93.45(16) . . ?

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
C6 C1 C2 C3 -0.3(5) . . . . ?
C7 C1 C2 C3 -175.7(4) . . . . ?
C1 C2 C3 C4 0.3(6) . . . . ?
C2 C3 C4 C5 0.9(7) . . . . ?
C3 C4 C5 C6 -2.1(6) . . . . ?
C2 C1 C6 C5 -1.0(5) . . . . ?
C7 C1 C6 C5 174.9(3) . . . . ?
C2 C1 C6 S1 179.9(3) . . . . ?
C7 C1 C6 S1 -4.2(3) . . . . ?
C4 C5 C6 C1 2.2(5) . . . . ?
C4 C5 C6 S1 -178.9(3) . . . . ?
C6 C1 C7 O4 -171.4(3) . . . . ?
C2 C1 C7 O4 4.3(5) . . . . ?
C6 C1 C7 C8 3.0(4) . . . . ?
C2 C1 C7 C8 178.6(3) . . . . ?
O4 C7 C8 N1 52.7(3) . . . . ?
C1 C7 C8 N1 -122.1(3) . . . . ?
O4 C7 C8 C11 -63.1(4) . . . . ?
C1 C7 C8 C11 122.2(3) . . . . ?
O4 C7 C8 S1 174.2(2) . . . . ?
C1 C7 C8 S1 -0.5(3) . . . . ?
C22 C9 C10 N1 -144.6(2) . . . . ?
C11 C9 C10 N1 -21.7(3) . . . . ?
C22 C9 C10 C21 95.2(3) . . . . ?
C11 C9 C10 C21 -141.9(3) . . . . ?
N1 C8 C11 C12 85.8(3) . . . . ?
C7 C8 C11 C12 -156.0(3) . . . . ?
S1 C8 C11 C12 -36.5(3) . . . . ?
N1 C8 C11 C18 -156.8(2) . . . . ?
C7 C8 C11 C18 -38.6(3) . . . . ?
S1 C8 C11 C18 80.9(2) . . . . ?
N1 C8 C11 C9 -35.8(2) . . . . ?
C7 C8 C11 C9 82.4(3) . . . . ?
S1 C8 C11 C9 -158.11(18) . . . . ?
C22 C9 C11 C12 38.3(3) . . . . ?
C10 C9 C11 C12 -86.9(3) . . . . ?
C22 C9 C11 C18 -76.9(3) . . . . ?
C10 C9 C11 C18 157.9(2) . . . . ?
C22 C9 C11 C8 159.9(2) . . . . ?
C10 C9 C11 C8 34.7(3) . . . . ?
C18 C11 C12 C13 -178.0(3) . . . . ?
C8 C11 C12 C13 -53.3(4) . . . . ?
C9 C11 C12 C13 61.1(4) . . . . ?
C18 C11 C12 C17 2.1(3) . . . . ?
C8 C11 C12 C17 126.8(3) . . . . ?
C9 C11 C12 C17 -118.7(3) . . . . ?
C17 C12 C13 C14 1.0(4) . . . . ?
C11 C12 C13 C14 -178.8(3) . . . . ?
C12 C13 C14 C15 1.3(5) . . . . ?
C13 C14 C15 C16 -2.2(5) . . . . ?
C14 C15 C16 C17 0.8(5) . . . . ?
C15 C16 C17 C12 1.6(5) . . . . ?
C15 C16 C17 N2 -177.9(3) . . . . ?
C13 C12 C17 C16 -2.5(5) . . . . ?
C11 C12 C17 C16 177.4(3) . . . . ?
C13 C12 C17 N2 177.0(3) . . . . ?
C11 C12 C17 N2 -3.1(3) . . . . ?
C12 C11 C18 O1 -179.1(3) . . . . ?
C8 C11 C18 O1 57.4(4) . . . . ?
C9 C11 C18 O1 -57.4(4) . . . . ?
C12 C11 C18 N2 -0.4(3) . . . . ?
C8 C11 C18 N2 -123.9(3) . . . . ?
C9 C11 C18 N2 121.3(3) . . . . ?
N1 C10 C21 F1 65.2(4) . . . . ?
C9 C10 C21 F1 -177.8(3) . . . . ?
N1 C10 C21 F2 -178.9(3) . . . . ?
C9 C10 C21 F2 -62.0(4) . . . . ?
C10 C9 C22 O2 0.0(4) . . . . ?
C11 C9 C22 O2 -118.4(3) . . . . ?
C10 C9 C22 O3 179.0(2) . . . . ?
C11 C9 C22 O3 60.5(3) . . . . ?
C11 C8 N1 C10 23.9(3) . . . . ?
C7 C8 N1 C10 -97.8(3) . . . . ?
S1 C8 N1 C10 145.2(2) . . . . ?
C21 C10 N1 C8 118.7(3) . . . . ?
C9 C10 N1 C8 -1.4(3) . . . . ?
O1 C18 N2 C17 177.2(3) . . . . ?
C11 C18 N2 C17 -1.4(3) . . . . ?
O1 C18 N2 C23 2.8(5) . . . . ?
C11 C18 N2 C23 -175.9(3) . . . . ?
C16 C17 N2 C18 -177.6(3) . . . . ?
C12 C17 N2 C18 2.9(3) . . . . ?
C16 C17 N2 C23 -3.3(5) . . . . ?
C12 C17 N2 C23 177.2(3) . . . . ?
O2 C22 O3 C19 1.5(5) . . . . ?
C9 C22 O3 C19 -177.5(3) . . . . ?
C20 C19 O3 C22 -175.8(3) . . . . ?
C1 C6 S1 C8 3.3(2) . . . . ?
C5 C6 S1 C8 -175.7(3) . . . . ?
N1 C8 S1 C6 117.3(2) . . . . ?
C11 C8 S1 C6 -125.6(2) . . . . ?
C7 C8 S1 C6 -1.5(2) . . . . ?

_refine_diff_density_max         0.202
_refine_diff_density_min         -0.170
_refine_diff_density_rms         0.033

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 2087189'
loop_
_audit_author_name
_audit_author_address
'yabo deng'
;lanzhou university
China
;
_audit_update_record             
;
2021-06-01 deposited with the CCDC.	2021-11-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H24 F2 N2 O4 S'
_chemical_formula_weight         486.52

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'
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'
F F 0.0171 0.0103 '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'

_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'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   9.5419(15)
_cell_length_b                   11.7937(19)
_cell_length_c                   21.380(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2405.9(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3972
_cell_measurement_theta_min      2.34
_cell_measurement_theta_max      21.20

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_F_000             1016
_exptl_transmission_factor_min   0.6434
_exptl_transmission_factor_max   0.7458
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.184
_shelx_estimated_absorpt_T_min   0.947
_shelx_estimated_absorpt_T_max   0.964
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX II area detector'
_diffrn_measurement_method       'ω scan'
_diffrn_detector_area_resol_mean 'fine-focus sealed tube'
_diffrn_reflns_number            20285
_diffrn_reflns_av_unetI/netI     0.0559
_diffrn_reflns_av_R_equivalents  0.0462
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         1.905
_diffrn_reflns_theta_max         29.186
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.952
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.952
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.931
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6057
_reflns_number_gt                3896
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.740
_reflns_Friedel_fraction_max     0.904
_reflns_Friedel_fraction_full    1.000

_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.
;

_computing_data_collection       'Bruker SMART APEX II'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0400P)²+0.3000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1275 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.10(5)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         6057
_refine_ls_number_parameters     311
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0823
_refine_ls_R_factor_gt           0.0457
_refine_ls_wR_factor_ref         0.1145
_refine_ls_wR_factor_gt          0.0996
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_restrained_S_all      0.996
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
C1 C -0.0613(4) 0.2093(3) 0.93575(15) 0.0555(8) Uani 1 1 d . . . . .
C2 C -0.0588(5) 0.2303(4) 1.00024(17) 0.0757(11) Uani 1 1 d . . . . .
H2 H -0.0054 0.2892 1.0166 0.091 Uiso 1 1 calc R U . . .
C3 C -0.1364(6) 0.1627(5) 1.0382(2) 0.0922(15) Uani 1 1 d . . . . .
H3 H -0.1372 0.1771 1.0810 0.111 Uiso 1 1 calc R U . . .
C4 C -0.2141(6) 0.0734(4) 1.0154(2) 0.0931(15) Uani 1 1 d . . . . .
H4 H -0.2646 0.0277 1.0427 0.112 Uiso 1 1 calc R U . . .
C5 C -0.2170(5) 0.0519(4) 0.9523(2) 0.0777(12) Uani 1 1 d . . . . .
H5 H -0.2700 -0.0077 0.9365 0.093 Uiso 1 1 calc R U . . .
C6 C -0.1396(3) 0.1204(3) 0.91255(15) 0.0546(8) Uani 1 1 d . . . . .
C7 C -0.1341(4) 0.1092(3) 0.84433(17) 0.0553(8) Uani 1 1 d . . . . .
C8 C -0.0226(3) 0.1917(3) 0.81553(14) 0.0481(7) Uani 1 1 d . . . . .
C9 C 0.1057(3) 0.1283(2) 0.78805(13) 0.0421(7) Uani 1 1 d . . . . .
C10 C 0.0475(3) 0.0910(3) 0.72340(13) 0.0488(7) Uani 1 1 d . . . . .
H10 H -0.0128 0.0249 0.7302 0.059 Uiso 1 1 calc R U . . .
C11 C -0.0468(4) 0.1900(3) 0.70381(15) 0.0555(8) Uani 1 1 d . . . . .
H11 H 0.0026 0.2391 0.6741 0.067 Uiso 1 1 calc R U . . .
C12 C -0.1803(4) 0.1447(4) 0.67449(19) 0.0777(12) Uani 1 1 d . . . . .
H12 H -0.2247 0.0885 0.7018 0.093 Uiso 1 1 calc R U . . .
C13 C 0.1557(3) 0.0288(3) 0.82833(15) 0.0507(8) Uani 1 1 d . . . . .
C14 C 0.3431(3) 0.1452(3) 0.81492(14) 0.0496(7) Uani 1 1 d . . . . .
C15 C 0.4764(4) 0.1888(3) 0.81747(18) 0.0689(10) Uani 1 1 d . . . . .
H15 H 0.5488 0.1500 0.8372 0.083 Uiso 1 1 calc R U . . .
C16 C 0.4986(4) 0.2940(4) 0.7891(2) 0.0781(12) Uani 1 1 d . . . . .
H16 H 0.5875 0.3263 0.7904 0.094 Uiso 1 1 calc R U . . .
C17 C 0.3930(4) 0.3504(4) 0.75946(18) 0.0716(11) Uani 1 1 d . . . . .
H17 H 0.4108 0.4211 0.7419 0.086 Uiso 1 1 calc R U . . .
C18 C 0.2596(4) 0.3046(3) 0.75491(16) 0.0559(8) Uani 1 1 d . . . . .
H18 H 0.1886 0.3422 0.7335 0.067 Uiso 1 1 calc R U . . .
C19 C 0.2357(3) 0.2009(3) 0.78341(14) 0.0456(7) Uani 1 1 d . . . . .
C20 C 0.3767(4) -0.0306(3) 0.87998(18) 0.0750(11) Uani 1 1 d . . . . .
H20A H 0.3169 -0.0856 0.8996 0.113 Uiso 1 1 calc R U . . .
H20B H 0.4244 0.0126 0.9115 0.113 Uiso 1 1 calc R U . . .
H20C H 0.4444 -0.0687 0.8542 0.113 Uiso 1 1 calc R U . . .
C21 C 0.1652(4) 0.0549(3) 0.68086(14) 0.0520(8) Uani 1 1 d . . . . .
C22 C 0.2944(5) 0.1051(4) 0.58533(18) 0.0764(11) Uani 1 1 d . . . . .
C23 C 0.2739(6) -0.0062(4) 0.5527(2) 0.0923(14) Uani 1 1 d . . . . .
H23A H 0.2902 -0.0671 0.5816 0.138 Uiso 1 1 calc R U . . .
H23B H 0.3386 -0.0120 0.5184 0.138 Uiso 1 1 calc R U . . .
H23C H 0.1797 -0.0108 0.5371 0.138 Uiso 1 1 calc R U . . .
C24 C 0.4348(5) 0.1125(5) 0.6170(3) 0.1144(18) Uani 1 1 d . . . . .
H24A H 0.4377 0.1788 0.6430 0.172 Uiso 1 1 calc R U . . .
H24B H 0.5072 0.1171 0.5859 0.172 Uiso 1 1 calc R U . . .
H24C H 0.4491 0.0463 0.6423 0.172 Uiso 1 1 calc R U . . .
C25 C 0.2659(8) 0.2021(5) 0.5404(3) 0.145(3) Uani 1 1 d . . . . .
H25A H 0.1703 0.1986 0.5265 0.218 Uiso 1 1 calc R U . . .
H25B H 0.3273 0.1960 0.5050 0.218 Uiso 1 1 calc R U . . .
H25C H 0.2820 0.2730 0.5613 0.218 Uiso 1 1 calc R U . . .
F1 F -0.2683(3) 0.2304(3) 0.66232(18) 0.1296(12) Uani 1 1 d . . . . .
F2 F -0.1470(3) 0.0986(4) 0.61884(15) 0.1568(15) Uani 1 1 d . . . . .
N1 N -0.0746(3) 0.2514(3) 0.76181(12) 0.0655(8) Uani 1 1 d . . . . .
H1 H -0.1171 0.3156 0.7636 0.079 Uiso 1 1 calc R U . . .
N2 N 0.2929(3) 0.0448(2) 0.84160(12) 0.0537(7) Uani 1 1 d . . . . .
O1 O -0.2067(3) 0.0521(2) 0.81284(13) 0.0757(8) Uani 1 1 d . . . . .
O2 O 0.2356(3) -0.0273(2) 0.69239(11) 0.0686(7) Uani 1 1 d . . . . .
O3 O 0.1806(3) 0.1224(2) 0.63194(11) 0.0655(7) Uani 1 1 d . . . . .
O4 O 0.0844(3) -0.0498(2) 0.84606(14) 0.0740(7) Uani 1 1 d . . . . .
S1 S 0.02948(10) 0.28723(7) 0.87908(4) 0.0621(3) Uani 1 1 d . . . . .


_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
C1 C6 1.379(5) . ?
C1 C2 1.401(5) . ?
C1 S1 1.750(4) . ?
C2 C3 1.358(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.376(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.372(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.386(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.465(5) . ?
C7 O1 1.177(4) . ?
C7 C8 1.567(5) . ?
C8 N1 1.436(4) . ?
C8 C9 1.549(4) . ?
C8 S1 1.834(3) . ?
C9 C19 1.511(4) . ?
C9 C13 1.532(4) . ?
C9 C10 1.553(4) . ?
C10 C21 1.507(4) . ?
C10 C11 1.532(4) . ?
C10 H10 0.9800 . ?
C11 N1 1.460(4) . ?
C11 C12 1.517(5) . ?
C11 H11 0.9800 . ?
C12 F1 1.340(5) . ?
C12 F2 1.346(5) . ?
C12 H12 0.9800 . ?
C13 O4 1.210(4) . ?
C13 N2 1.353(4) . ?
C14 C15 1.374(5) . ?
C14 C19 1.391(4) . ?
C14 N2 1.398(4) . ?
C15 C16 1.397(6) . ?
C15 H15 0.9300 . ?
C16 C17 1.364(6) . ?
C16 H16 0.9300 . ?
C17 C18 1.385(5) . ?
C17 H17 0.9300 . ?
C18 C19 1.385(5) . ?
C18 H18 0.9300 . ?
C20 N2 1.451(4) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 O2 1.205(4) . ?
C21 O3 1.323(4) . ?
C22 O3 1.487(4) . ?
C22 C23 1.500(6) . ?
C22 C24 1.504(7) . ?
C22 C25 1.518(7) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
N1 H1 0.8600 . ?

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
C6 C1 C2 119.8(3) . . ?
C6 C1 S1 114.7(2) . . ?
C2 C1 S1 125.4(3) . . ?
C3 C2 C1 118.3(4) . . ?
C3 C2 H2 120.8 . . ?
C1 C2 H2 120.8 . . ?
C2 C3 C4 122.1(4) . . ?
C2 C3 H3 119.0 . . ?
C4 C3 H3 119.0 . . ?
C5 C4 C3 120.0(4) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C5 C6 119.0(5) . . ?
C4 C5 H5 120.5 . . ?
C6 C5 H5 120.5 . . ?
C1 C6 C5 120.7(3) . . ?
C1 C6 C7 114.0(3) . . ?
C5 C6 C7 125.3(4) . . ?
O1 C7 C6 126.8(4) . . ?
O1 C7 C8 122.0(3) . . ?
C6 C7 C8 111.1(3) . . ?
N1 C8 C9 101.9(2) . . ?
N1 C8 C7 112.6(3) . . ?
C9 C8 C7 112.7(2) . . ?
N1 C8 S1 112.6(2) . . ?
C9 C8 S1 111.3(2) . . ?
C7 C8 S1 105.9(2) . . ?
C19 C9 C13 102.4(2) . . ?
C19 C9 C8 113.6(2) . . ?
C13 C9 C8 113.7(2) . . ?
C19 C9 C10 113.3(2) . . ?
C13 C9 C10 113.2(2) . . ?
C8 C9 C10 101.1(2) . . ?
C21 C10 C11 119.2(3) . . ?
C21 C10 C9 110.5(3) . . ?
C11 C10 C9 103.7(2) . . ?
C21 C10 H10 107.6 . . ?
C11 C10 H10 107.6 . . ?
C9 C10 H10 107.6 . . ?
N1 C11 C12 111.9(3) . . ?
N1 C11 C10 104.6(2) . . ?
C12 C11 C10 109.8(3) . . ?
N1 C11 H11 110.1 . . ?
C12 C11 H11 110.1 . . ?
C10 C11 H11 110.1 . . ?
F1 C12 F2 106.3(4) . . ?
F1 C12 C11 110.0(3) . . ?
F2 C12 C11 108.0(3) . . ?
F1 C12 H12 110.8 . . ?
F2 C12 H12 110.8 . . ?
C11 C12 H12 110.8 . . ?
O4 C13 N2 125.8(3) . . ?
O4 C13 C9 126.0(3) . . ?
N2 C13 C9 108.2(3) . . ?
C15 C14 C19 121.6(3) . . ?
C15 C14 N2 128.2(3) . . ?
C19 C14 N2 110.2(3) . . ?
C14 C15 C16 117.1(4) . . ?
C14 C15 H15 121.4 . . ?
C16 C15 H15 121.4 . . ?
C17 C16 C15 121.5(3) . . ?
C17 C16 H16 119.3 . . ?
C15 C16 H16 119.3 . . ?
C16 C17 C18 121.5(4) . . ?
C16 C17 H17 119.3 . . ?
C18 C17 H17 119.3 . . ?
C19 C18 C17 117.7(4) . . ?
C19 C18 H18 121.2 . . ?
C17 C18 H18 121.2 . . ?
C18 C19 C14 120.6(3) . . ?
C18 C19 C9 131.6(3) . . ?
C14 C19 C9 107.8(3) . . ?
N2 C20 H20A 109.5 . . ?
N2 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
N2 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O2 C21 O3 125.7(3) . . ?
O2 C21 C10 121.3(3) . . ?
O3 C21 C10 113.0(3) . . ?
O3 C22 C23 109.7(3) . . ?
O3 C22 C24 109.9(3) . . ?
C23 C22 C24 112.1(4) . . ?
O3 C22 C25 100.9(4) . . ?
C23 C22 C25 110.0(4) . . ?
C24 C22 C25 113.6(5) . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C22 C24 H24A 109.5 . . ?
C22 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C22 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C22 C25 H25A 109.5 . . ?
C22 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C22 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C8 N1 C11 111.9(2) . . ?
C8 N1 H1 124.0 . . ?
C11 N1 H1 124.0 . . ?
C13 N2 C14 111.4(3) . . ?
C13 N2 C20 124.5(3) . . ?
C14 N2 C20 124.1(3) . . ?
C21 O3 C22 121.9(3) . . ?
C1 S1 C8 93.21(15) . . ?

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
C6 C1 C2 C3 -1.0(6) . . . . ?
S1 C1 C2 C3 179.3(3) . . . . ?
C1 C2 C3 C4 1.5(7) . . . . ?
C2 C3 C4 C5 -1.4(8) . . . . ?
C3 C4 C5 C6 0.7(7) . . . . ?
C2 C1 C6 C5 0.4(5) . . . . ?
S1 C1 C6 C5 -179.8(3) . . . . ?
C2 C1 C6 C7 179.2(3) . . . . ?
S1 C1 C6 C7 -1.1(4) . . . . ?
C4 C5 C6 C1 -0.3(6) . . . . ?
C4 C5 C6 C7 -178.9(4) . . . . ?
C1 C6 C7 O1 -167.9(3) . . . . ?
C5 C6 C7 O1 10.8(6) . . . . ?
C1 C6 C7 C8 8.0(4) . . . . ?
C5 C6 C7 C8 -173.3(3) . . . . ?
O1 C7 C8 N1 41.9(4) . . . . ?
C6 C7 C8 N1 -134.3(3) . . . . ?
O1 C7 C8 C9 -72.7(4) . . . . ?
C6 C7 C8 C9 111.1(3) . . . . ?
O1 C7 C8 S1 165.4(3) . . . . ?
C6 C7 C8 S1 -10.8(3) . . . . ?
N1 C8 C9 C19 81.7(3) . . . . ?
C7 C8 C9 C19 -157.4(3) . . . . ?
S1 C8 C9 C19 -38.6(3) . . . . ?
N1 C8 C9 C13 -161.6(3) . . . . ?
C7 C8 C9 C13 -40.7(3) . . . . ?
S1 C8 C9 C13 78.1(3) . . . . ?
N1 C8 C9 C10 -40.0(3) . . . . ?
C7 C8 C9 C10 80.9(3) . . . . ?
S1 C8 C9 C10 -160.3(2) . . . . ?
C19 C9 C10 C21 42.9(3) . . . . ?
C13 C9 C10 C21 -73.3(3) . . . . ?
C8 C9 C10 C21 164.7(3) . . . . ?
C19 C9 C10 C11 -86.1(3) . . . . ?
C13 C9 C10 C11 157.8(3) . . . . ?
C8 C9 C10 C11 35.8(3) . . . . ?
C21 C10 C11 N1 -142.0(3) . . . . ?
C9 C10 C11 N1 -18.5(3) . . . . ?
C21 C10 C11 C12 97.8(4) . . . . ?
C9 C10 C11 C12 -138.8(3) . . . . ?
N1 C11 C12 F1 58.9(4) . . . . ?
C10 C11 C12 F1 174.6(3) . . . . ?
N1 C11 C12 F2 174.5(3) . . . . ?
C10 C11 C12 F2 -69.8(4) . . . . ?
C19 C9 C13 O4 177.5(3) . . . . ?
C8 C9 C13 O4 54.5(4) . . . . ?
C10 C9 C13 O4 -60.1(4) . . . . ?
C19 C9 C13 N2 -1.4(3) . . . . ?
C8 C9 C13 N2 -124.4(3) . . . . ?
C10 C9 C13 N2 121.0(3) . . . . ?
C19 C14 C15 C16 2.4(5) . . . . ?
N2 C14 C15 C16 -177.2(3) . . . . ?
C14 C15 C16 C17 -0.7(5) . . . . ?
C15 C16 C17 C18 -1.6(6) . . . . ?
C16 C17 C18 C19 2.2(5) . . . . ?
C17 C18 C19 C14 -0.5(4) . . . . ?
C17 C18 C19 C9 179.6(3) . . . . ?
C15 C14 C19 C18 -1.8(5) . . . . ?
N2 C14 C19 C18 177.8(3) . . . . ?
C15 C14 C19 C9 178.1(3) . . . . ?
N2 C14 C19 C9 -2.2(3) . . . . ?
C13 C9 C19 C18 -177.9(3) . . . . ?
C8 C9 C19 C18 -54.8(4) . . . . ?
C10 C9 C19 C18 59.8(4) . . . . ?
C13 C9 C19 C14 2.2(3) . . . . ?
C8 C9 C19 C14 125.2(3) . . . . ?
C10 C9 C19 C14 -120.2(3) . . . . ?
C11 C10 C21 O2 -174.8(3) . . . . ?
C9 C10 C21 O2 65.2(4) . . . . ?
C11 C10 C21 O3 5.6(4) . . . . ?
C9 C10 C21 O3 -114.4(3) . . . . ?
C9 C8 N1 C11 30.6(3) . . . . ?
C7 C8 N1 C11 -90.4(3) . . . . ?
S1 C8 N1 C11 149.9(2) . . . . ?
C12 C11 N1 C8 111.1(3) . . . . ?
C10 C11 N1 C8 -7.7(4) . . . . ?
O4 C13 N2 C14 -178.8(3) . . . . ?
C9 C13 N2 C14 0.2(3) . . . . ?
O4 C13 N2 C20 -0.3(5) . . . . ?
C9 C13 N2 C20 178.6(3) . . . . ?
C15 C14 N2 C13 -179.1(3) . . . . ?
C19 C14 N2 C13 1.3(4) . . . . ?
C15 C14 N2 C20 2.5(5) . . . . ?
C19 C14 N2 C20 -177.2(3) . . . . ?
O2 C21 O3 C22 -2.1(5) . . . . ?
C10 C21 O3 C22 177.4(3) . . . . ?
C23 C22 O3 C21 63.9(5) . . . . ?
C24 C22 O3 C21 -59.8(5) . . . . ?
C25 C22 O3 C21 179.9(4) . . . . ?
C6 C1 S1 C8 -5.0(3) . . . . ?
C2 C1 S1 C8 174.7(3) . . . . ?
N1 C8 S1 C1 132.2(2) . . . . ?
C9 C8 S1 C1 -114.1(2) . . . . ?
C7 C8 S1 C1 8.7(2) . . . . ?

_refine_diff_density_max         0.199
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.035

