# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2022

####################################################################### 
# 
# 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_mx9225
_database_code_depnum_ccdc_archive 'CCDC 2090638'
loop_
_audit_author_name
_audit_author_address
zhang
;Institute of Chemistry, Chinese Academy of Sciences
China
;
_audit_update_record             
;
2021-06-17 deposited with the CCDC.	2022-01-16 downloaded from the CCDC.
;
_audit_creation_date             2021-02-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H20 F N5 O6 S2'
_chemical_formula_sum            'C22 H20 F N5 O6 S2'
_chemical_formula_weight         533.55
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHNOFS
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           18
_space_group_name_H-M_alt        'P 21 21 2'
_space_group_name_Hall           'P 2 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-x+1/2, y+1/2, -z'
'x+1/2, -y+1/2, -z'

_cell_length_a                   8.0935(2)
_cell_length_b                   24.6442(7)
_cell_length_c                   11.6534(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2324.36(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    10457
_cell_measurement_temperature    170.00(10)
_cell_measurement_theta_max      30.9800
_cell_measurement_theta_min      1.6210
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.288
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83022
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.45i (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.525
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1104
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0190
_diffrn_reflns_av_unetI/netI     0.0211
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            16440
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.496
_diffrn_reflns_theta_min         1.653
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      170.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -7.00  67.00   0.50   10.00    --  -11.60  45.00 178.24  148
  2  ω   -101.00  76.00   0.50   10.00    --  -11.60  45.00  27.53  354
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC10 (RCD3): fixed-chi single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0004624000
_diffrn_orient_matrix_UB_12      0.0287844000
_diffrn_orient_matrix_UB_13      -0.0016305000
_diffrn_orient_matrix_UB_21      -0.0856982000
_diffrn_orient_matrix_UB_22      0.0000766000
_diffrn_orient_matrix_UB_23      0.0127043000
_diffrn_orient_matrix_UB_31      0.0183569000
_diffrn_orient_matrix_UB_32      0.0008541000
_diffrn_orient_matrix_UB_33      0.0594665000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.754
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                5091
_reflns_number_total             5355
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_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 1.171.39.45i (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.45i (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.45i (Rigaku OD, 2018)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.144
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details 
;
 Flack x determined using 2097 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.016(17)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     330
_refine_ls_number_reflns         5355
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0269
_refine_ls_R_factor_gt           0.0249
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0334P)²+0.4329P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0620
_refine_ls_wR_factor_ref         0.0630
_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:
 C10(H10A,H10B), C12(H12A,H12B), C13(H13A,H13B), C14(H14A,H14B), C15(H15A,H15B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3A), C4(H4), C6(H6), C18(H18), C19(H19), C21(H21)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.43665(6) 0.64856(2) 0.61659(4) 0.02598(11) Uani 1 1 d . . . . .
S2 S 0.49712(6) 0.76576(2) 0.69483(5) 0.02754(12) Uani 1 1 d . . . . .
F1 F 0.98793(19) 0.89522(5) 0.75787(15) 0.0525(4) Uani 1 1 d . . . . .
O1 O 0.64454(19) 0.57876(6) 0.82282(13) 0.0307(3) Uani 1 1 d . . . . .
O2 O 0.60577(17) 0.66539(5) 0.87427(12) 0.0253(3) Uani 1 1 d . . . . .
O3 O 0.0699(2) 0.41095(6) 0.68341(12) 0.0313(3) Uani 1 1 d . . . . .
O4 O -0.04144(19) 0.36441(6) 0.54704(14) 0.0323(3) Uani 1 1 d . . . . .
O5 O 0.0951(2) 0.38697(7) 0.16263(14) 0.0441(4) Uani 1 1 d . . . . .
O6 O 0.2147(3) 0.46006(8) 0.10345(14) 0.0514(5) Uani 1 1 d . . . . .
N1 N 0.7267(2) 0.70084(7) 0.62255(15) 0.0256(3) Uani 1 1 d . . . . .
N2 N 0.3091(2) 0.54930(6) 0.65180(14) 0.0224(3) Uani 1 1 d . . . . .
N3 N 0.2366(2) 0.49944(7) 0.63488(14) 0.0240(3) Uani 1 1 d . . . . .
N4 N 0.0488(2) 0.40078(6) 0.58098(14) 0.0237(3) Uani 1 1 d . . . . .
N5 N 0.1624(2) 0.43092(8) 0.18032(16) 0.0331(4) Uani 1 1 d . . . . .
C1 C 0.5704(3) 0.70348(7) 0.64340(16) 0.0232(4) Uani 1 1 d . . . . .
C2 C 0.8024(2) 0.74964(8) 0.64971(17) 0.0246(4) Uani 1 1 d . . . . .
C3 C 0.9725(3) 0.75991(9) 0.6410(2) 0.0321(5) Uani 1 1 d . . . . .
H3A H 1.043396 0.733698 0.611453 0.038 Uiso 1 1 calc R . . . .
C4 C 1.0326(3) 0.80912(9) 0.6765(2) 0.0364(5) Uani 1 1 d . . . . .
H4 H 1.144825 0.816776 0.671244 0.044 Uiso 1 1 calc R . . . .
C5 C 0.9241(3) 0.84727(8) 0.7203(2) 0.0339(5) Uani 1 1 d . . . . .
C6 C 0.7573(3) 0.84006(8) 0.73077(19) 0.0299(4) Uani 1 1 d . . . . .
H6 H 0.688447 0.866728 0.760805 0.036 Uiso 1 1 calc R . . . .
C7 C 0.6971(2) 0.79002(8) 0.69334(18) 0.0246(4) Uani 1 1 d . . . . .
C8 C 0.3947(2) 0.62379(7) 0.76496(15) 0.0205(4) Uani 1 1 d . . . . .
C9 C 0.5621(2) 0.61908(7) 0.82377(15) 0.0215(4) Uani 1 1 d . . . . .
C10 C 0.7726(3) 0.66666(9) 0.92102(19) 0.0312(5) Uani 1 1 d . . . . .
H10A H 0.853365 0.664895 0.859657 0.037 Uiso 1 1 calc R . . . .
H10B H 0.790077 0.636112 0.972081 0.037 Uiso 1 1 calc R . . . .
C11 C 0.7890(3) 0.71902(10) 0.9854(3) 0.0454(6) Uani 1 1 d . . . . .
H11A H 0.774970 0.748877 0.933416 0.068 Uiso 1 1 calc GR . . . .
H11B H 0.896494 0.720969 1.019962 0.068 Uiso 1 1 calc GR . . . .
H11C H 0.705956 0.720752 1.044150 0.068 Uiso 1 1 calc GR . . . .
C12 C 0.2717(2) 0.66009(7) 0.82989(17) 0.0233(4) Uani 1 1 d . . . . .
H12A H 0.319639 0.695794 0.840824 0.028 Uiso 1 1 calc R . . . .
H12B H 0.171822 0.664193 0.784730 0.028 Uiso 1 1 calc R . . . .
C13 C 0.2285(3) 0.63550(8) 0.94684(17) 0.0273(4) Uani 1 1 d . . . . .
H13A H 0.327552 0.633068 0.993368 0.033 Uiso 1 1 calc R . . . .
H13B H 0.150651 0.658966 0.986155 0.033 Uiso 1 1 calc R . . . .
C14 C 0.1534(3) 0.57933(8) 0.93322(18) 0.0287(4) Uani 1 1 d . . . . .
H14A H 0.047485 0.582402 0.894763 0.034 Uiso 1 1 calc R . . . .
H14B H 0.134318 0.563717 1.008472 0.034 Uiso 1 1 calc R . . . .
C15 C 0.2658(3) 0.54178(8) 0.86422(17) 0.0262(4) Uani 1 1 d . . . . .
H15A H 0.362168 0.532774 0.909865 0.031 Uiso 1 1 calc R . . . .
H15B H 0.207274 0.508340 0.847612 0.031 Uiso 1 1 calc R . . . .
C16 C 0.3206(2) 0.56734(7) 0.75356(16) 0.0215(4) Uani 1 1 d . . . . .
C17 C 0.2178(2) 0.48231(7) 0.52566(16) 0.0205(4) Uani 1 1 d . . . . .
C18 C 0.2815(3) 0.51313(7) 0.43333(17) 0.0253(4) Uani 1 1 d . . . . .
H18 H 0.337043 0.545309 0.449086 0.030 Uiso 1 1 calc R . . . .
C19 C 0.2640(2) 0.49717(8) 0.32189(16) 0.0268(4) Uani 1 1 d . . . . .
H19 H 0.306877 0.518163 0.262628 0.032 Uiso 1 1 calc R . . . .
C20 C 0.1806(2) 0.44879(8) 0.29819(17) 0.0249(4) Uani 1 1 d . . . . .
C21 C 0.1151(2) 0.41762(8) 0.38390(17) 0.0232(4) Uani 1 1 d . . . . .
H21 H 0.059604 0.385620 0.366555 0.028 Uiso 1 1 calc R . . . .
C22 C 0.1323(2) 0.43415(7) 0.49647(16) 0.0211(4) Uani 1 1 d . . . . .
H3 H 0.220(3) 0.4786(10) 0.685(2) 0.028(6) Uiso 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
S1 C1 1.7613(19) . ?
S1 C8 1.8646(19) . ?
S2 C1 1.7512(19) . ?
S2 C7 1.726(2) . ?
F1 C5 1.362(2) . ?
O1 C9 1.197(2) . ?
O2 C9 1.332(2) . ?
O2 C10 1.456(2) . ?
O3 N4 1.232(2) . ?
O4 N4 1.222(2) . ?
O5 N5 1.230(2) . ?
O6 N5 1.224(3) . ?
N1 C1 1.289(3) . ?
N1 C2 1.386(2) . ?
N2 N3 1.376(2) . ?
N2 C16 1.270(2) . ?
N3 C17 1.350(2) . ?
N4 C22 1.450(2) . ?
N5 C20 1.450(3) . ?
C2 C3 1.403(3) . ?
C2 C7 1.405(3) . ?
C3 C4 1.371(3) . ?
C4 C5 1.384(3) . ?
C5 C6 1.367(3) . ?
C6 C7 1.396(3) . ?
C8 C9 1.522(3) . ?
C8 C12 1.538(3) . ?
C8 C16 1.521(3) . ?
C10 C11 1.499(3) . ?
C12 C13 1.532(3) . ?
C13 C14 1.520(3) . ?
C14 C15 1.527(3) . ?
C15 C16 1.502(3) . ?
C17 C18 1.414(3) . ?
C17 C22 1.415(3) . ?
C18 C19 1.364(3) . ?
C19 C20 1.397(3) . ?
C20 C21 1.367(3) . ?
C21 C22 1.381(3) . ?

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
C1 S1 C8 101.47(9) . . ?
C7 S2 C1 88.99(10) . . ?
C9 O2 C10 115.47(15) . . ?
C1 N1 C2 110.30(17) . . ?
C16 N2 N3 118.55(16) . . ?
C17 N3 N2 117.56(16) . . ?
O3 N4 C22 118.58(15) . . ?
O4 N4 O3 123.08(16) . . ?
O4 N4 C22 118.33(16) . . ?
O5 N5 C20 118.13(18) . . ?
O6 N5 O5 123.19(19) . . ?
O6 N5 C20 118.68(18) . . ?
S2 C1 S1 121.73(12) . . ?
N1 C1 S1 122.06(15) . . ?
N1 C1 S2 116.17(15) . . ?
N1 C2 C3 125.00(19) . . ?
N1 C2 C7 115.39(18) . . ?
C3 C2 C7 119.56(18) . . ?
C4 C3 C2 119.05(19) . . ?
C3 C4 C5 119.17(19) . . ?
F1 C5 C4 117.9(2) . . ?
F1 C5 C6 117.3(2) . . ?
C6 C5 C4 124.8(2) . . ?
C5 C6 C7 115.6(2) . . ?
C2 C7 S2 109.09(14) . . ?
C6 C7 S2 129.06(16) . . ?
C6 C7 C2 121.82(18) . . ?
C9 C8 S1 106.30(12) . . ?
C9 C8 C12 113.51(15) . . ?
C12 C8 S1 112.56(13) . . ?
C16 C8 S1 106.87(12) . . ?
C16 C8 C9 108.69(15) . . ?
C16 C8 C12 108.64(15) . . ?
O1 C9 O2 124.56(18) . . ?
O1 C9 C8 123.72(17) . . ?
O2 C9 C8 111.71(15) . . ?
O2 C10 C11 106.74(18) . . ?
C13 C12 C8 110.84(15) . . ?
C14 C13 C12 111.02(16) . . ?
C13 C14 C15 111.64(17) . . ?
C16 C15 C14 111.97(16) . . ?
N2 C16 C8 115.52(16) . . ?
N2 C16 C15 129.28(17) . . ?
C15 C16 C8 115.16(16) . . ?
N3 C17 C18 120.56(17) . . ?
N3 C17 C22 122.97(17) . . ?
C18 C17 C22 116.46(17) . . ?
C19 C18 C17 122.12(18) . . ?
C18 C19 C20 118.95(18) . . ?
C19 C20 N5 119.71(18) . . ?
C21 C20 N5 118.81(18) . . ?
C21 C20 C19 121.49(18) . . ?
C20 C21 C22 119.31(18) . . ?
C17 C22 N4 122.69(17) . . ?
C21 C22 N4 115.55(16) . . ?
C21 C22 C17 121.66(17) . . ?

_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 1.481
_oxdiff_exptl_absorpt_empirical_full_min 0.847
