# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ns2nf
_audit_block_doi                 10.5517/ccdc.csd.cc2f02h1
_database_code_depnum_ccdc_archive 'CCDC 2234402'
loop_
_audit_author_name
_audit_author_address
'Kohsuke Aikawa'
;The University of Tokyo
Japan
;
_audit_update_record             
;
2023-05-02 deposited with the CCDC.	2023-06-22 downloaded from the CCDC.
;
_audit_creation_date             2021-03-16
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H8 F N3 O8 S2'
_chemical_formula_sum            'C12 H8 F N3 O8 S2'
_chemical_formula_weight         405.33
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_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                   7.8287(6)
_cell_length_b                   17.6965(12)
_cell_length_c                   11.4149(10)
_cell_angle_alpha                90
_cell_angle_beta                 103.482(9)
_cell_angle_gamma                90
_cell_volume                     1537.8(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    54331
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      30.4330
_cell_measurement_theta_min      2.2170
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.410
_exptl_absorpt_correction_T_max  0.877
_exptl_absorpt_correction_T_min  0.855
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.99a (Rigaku Oxford Diffraction, 2021)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.751
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0449
_diffrn_reflns_av_unetI/netI     0.0364
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.901
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10101
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.901
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.371
_diffrn_reflns_theta_min         2.166
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.901
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3083
_reflns_number_total             3473
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.501
_refine_diff_density_min         -0.445
_refine_diff_density_rms         0.072
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3473
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0409
_refine_ls_R_factor_gt           0.0368
_refine_ls_restrained_S_all      1.060
_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)+(0.0633P)²+0.4221P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1030
_refine_ls_wR_factor_ref         0.1049
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00H(H00H), C00J(H00J), C00L(H00L), C00M(H00M), C00N(H00N), C00O(H00O),
 C00P(H00P), C00Q(H00Q)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S001 S 0.25255(5) 0.63089(2) 0.33619(3) 0.01710(12) Uani 1 1 d . . . . .
S002 S 0.51352(5) 0.52180(2) 0.27562(3) 0.01817(12) Uani 1 1 d . . . . .
F003 F 0.27789(14) 0.49319(5) 0.39246(10) 0.0277(3) Uani 1 1 d . . . . .
O004 O 0.35202(16) 0.68373(6) 0.28626(11) 0.0214(3) Uani 1 1 d . . . . .
O005 O 0.63663(16) 0.58144(7) 0.28059(11) 0.0235(3) Uani 1 1 d . . . . .
O006 O 0.56516(16) 0.44757(6) 0.31609(11) 0.0244(3) Uani 1 1 d . . . . .
O007 O 0.08513(16) 0.60523(7) 0.26957(11) 0.0255(3) Uani 1 1 d . . . . .
O008 O 0.61241(16) 0.67051(7) 0.50587(13) 0.0298(3) Uani 1 1 d . . . . .
O009 O 0.39047(19) 0.32996(7) 0.11835(13) 0.0316(3) Uani 1 1 d . . . . .
O00A O 0.5725(2) 0.78994(8) 0.53107(14) 0.0389(4) Uani 1 1 d . . . . .
O00B O 0.2126(2) 0.37379(8) 0.22168(13) 0.0387(4) Uani 1 1 d . . . . .
N00C N 0.52587(19) 0.72393(8) 0.52742(13) 0.0220(3) Uani 1 1 d . . . . .
N00D N 0.2991(2) 0.37971(8) 0.14654(13) 0.0228(3) Uani 1 1 d . . . . .
N00E N 0.38856(19) 0.55276(7) 0.37363(13) 0.0195(3) Uani 1 1 d . . . . .
C00F C 0.2292(2) 0.66207(9) 0.47791(14) 0.0173(3) Uani 1 1 d . . . . .
C00G C 0.2871(2) 0.45156(9) 0.07948(14) 0.0182(3) Uani 1 1 d . . . . .
C00H C 0.3614(2) 0.58180(9) 0.05728(15) 0.0204(3) Uani 1 1 d . . . . .
H00H H 0.421117 0.625648 0.087536 0.025 Uiso 1 1 calc R U . . .
C00I C 0.3540(2) 0.70831(9) 0.55308(15) 0.0177(3) Uani 1 1 d . . . . .
C00J C 0.0690(2) 0.65009(11) 0.50633(16) 0.0243(4) Uani 1 1 d . . . . .
H00J H -0.016064 0.620395 0.456667 0.029 Uiso 1 1 calc R U . . .
C00K C 0.3756(2) 0.51731(9) 0.12884(14) 0.0176(3) Uani 1 1 d . . . . .
C00L C 0.3206(2) 0.74164(9) 0.65424(15) 0.0230(4) Uani 1 1 d . . . . .
H00L H 0.403987 0.772634 0.702707 0.028 Uiso 1 1 calc R U . . .
C00M C 0.1843(2) 0.45014(10) -0.03657(15) 0.0219(3) Uani 1 1 d . . . . .
H00M H 0.126744 0.406069 -0.068021 0.026 Uiso 1 1 calc R U . . .
C00N C 0.2574(2) 0.58046(10) -0.05967(15) 0.0228(4) Uani 1 1 d . . . . .
H00N H 0.247998 0.623637 -0.107184 0.027 Uiso 1 1 calc R U . . .
C00O C 0.1682(2) 0.51572(10) -0.10590(16) 0.0223(4) Uani 1 1 d . . . . .
H00O H 0.097158 0.515880 -0.183537 0.027 Uiso 1 1 calc R U . . .
C00P C 0.1603(3) 0.72830(11) 0.68291(17) 0.0278(4) Uani 1 1 d . . . . .
H00P H 0.136395 0.750018 0.751549 0.033 Uiso 1 1 calc R U . . .
C00Q C 0.0359(2) 0.68273(11) 0.60960(17) 0.0300(4) Uani 1 1 d . . . . .
H00Q H -0.070901 0.673885 0.629666 0.036 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
S001 O004 1.4187(12) . ?
S001 O007 1.4275(12) . ?
S001 N00E 1.7366(14) . ?
S001 C00F 1.7584(16) . ?
S002 O005 1.4214(12) . ?
S002 O006 1.4197(12) . ?
S002 N00E 1.7376(15) . ?
S002 C00K 1.7709(16) . ?
F003 N00E 1.4125(16) . ?
O008 N00C 1.2210(19) . ?
O009 N00D 1.224(2) . ?
O00A N00C 1.2216(19) . ?
O00B N00D 1.215(2) . ?
N00C C00I 1.469(2) . ?
N00D C00G 1.476(2) . ?
C00F C00I 1.403(2) . ?
C00F C00J 1.383(2) . ?
C00G C00K 1.403(2) . ?
C00G C00M 1.380(2) . ?
C00H H00H 0.9300 . ?
C00H C00K 1.393(2) . ?
C00H C00N 1.392(2) . ?
C00I C00L 1.375(2) . ?
C00J H00J 0.9300 . ?
C00J C00Q 1.390(3) . ?
C00L H00L 0.9300 . ?
C00L C00P 1.389(3) . ?
C00M H00M 0.9300 . ?
C00M C00O 1.394(2) . ?
C00N H00N 0.9300 . ?
C00N C00O 1.381(2) . ?
C00O H00O 0.9300 . ?
C00P H00P 0.9300 . ?
C00P C00Q 1.385(3) . ?
C00Q H00Q 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
O004 S001 O007 121.17(8) . . ?
O004 S001 N00E 105.14(7) . . ?
O004 S001 C00F 110.32(7) . . ?
O007 S001 N00E 108.17(7) . . ?
O007 S001 C00F 108.09(8) . . ?
N00E S001 C00F 102.27(7) . . ?
O005 S002 N00E 102.62(7) . . ?
O005 S002 C00K 109.23(7) . . ?
O006 S002 O005 122.35(8) . . ?
O006 S002 N00E 104.04(7) . . ?
O006 S002 C00K 109.32(7) . . ?
N00E S002 C00K 108.22(7) . . ?
O008 N00C O00A 124.88(16) . . ?
O008 N00C C00I 118.15(14) . . ?
O00A N00C C00I 116.97(15) . . ?
O009 N00D C00G 117.01(14) . . ?
O00B N00D O009 125.44(15) . . ?
O00B N00D C00G 117.49(15) . . ?
S001 N00E S002 119.84(8) . . ?
F003 N00E S001 105.61(9) . . ?
F003 N00E S002 108.66(9) . . ?
C00I C00F S001 122.61(12) . . ?
C00J C00F S001 117.51(13) . . ?
C00J C00F C00I 119.07(15) . . ?
C00K C00G N00D 122.70(14) . . ?
C00M C00G N00D 115.76(14) . . ?
C00M C00G C00K 121.54(15) . . ?
C00K C00H H00H 120.1 . . ?
C00N C00H H00H 120.1 . . ?
C00N C00H C00K 119.82(15) . . ?
C00F C00I N00C 121.82(14) . . ?
C00L C00I N00C 116.70(15) . . ?
C00L C00I C00F 121.48(15) . . ?
C00F C00J H00J 120.2 . . ?
C00F C00J C00Q 119.59(17) . . ?
C00Q C00J H00J 120.2 . . ?
C00G C00K S002 123.52(12) . . ?
C00H C00K S002 117.76(12) . . ?
C00H C00K C00G 118.65(15) . . ?
C00I C00L H00L 120.5 . . ?
C00I C00L C00P 118.96(17) . . ?
C00P C00L H00L 120.5 . . ?
C00G C00M H00M 120.5 . . ?
C00G C00M C00O 119.02(16) . . ?
C00O C00M H00M 120.5 . . ?
C00H C00N H00N 119.6 . . ?
C00O C00N C00H 120.74(16) . . ?
C00O C00N H00N 119.6 . . ?
C00M C00O H00O 119.9 . . ?
C00N C00O C00M 120.20(16) . . ?
C00N C00O H00O 119.9 . . ?
C00L C00P H00P 119.9 . . ?
C00Q C00P C00L 120.21(17) . . ?
C00Q C00P H00P 119.9 . . ?
C00J C00Q H00Q 119.7 . . ?
C00P C00Q C00J 120.68(17) . . ?
C00P C00Q H00Q 119.7 . . ?

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
S001 C00F C00I N00C -10.0(2) . . . . ?
S001 C00F C00I C00L 169.61(13) . . . . ?
S001 C00F C00J C00Q -171.17(14) . . . . ?
O004 S001 N00E S002 -41.72(11) . . . . ?
O004 S001 N00E F003 -164.63(9) . . . . ?
O004 S001 C00F C00I -28.42(15) . . . . ?
O004 S001 C00F C00J 141.12(13) . . . . ?
O005 S002 N00E S001 67.87(10) . . . . ?
O005 S002 N00E F003 -170.72(9) . . . . ?
O005 S002 C00K C00G 155.53(13) . . . . ?
O005 S002 C00K C00H -21.44(15) . . . . ?
O006 S002 N00E S001 -163.73(9) . . . . ?
O006 S002 N00E F003 -42.32(11) . . . . ?
O006 S002 C00K C00G 19.25(16) . . . . ?
O006 S002 C00K C00H -157.73(13) . . . . ?
O007 S001 N00E S002 89.05(10) . . . . ?
O007 S001 N00E F003 -33.85(11) . . . . ?
O007 S001 C00F C00I -162.97(13) . . . . ?
O007 S001 C00F C00J 6.57(15) . . . . ?
O008 N00C C00I C00F -49.8(2) . . . . ?
O008 N00C C00I C00L 130.59(16) . . . . ?
O009 N00D C00G C00K -104.89(18) . . . . ?
O009 N00D C00G C00M 74.28(19) . . . . ?
O00A N00C C00I C00F 131.24(17) . . . . ?
O00A N00C C00I C00L -48.4(2) . . . . ?
O00B N00D C00G C00K 77.9(2) . . . . ?
O00B N00D C00G C00M -102.96(18) . . . . ?
N00C C00I C00L C00P -179.61(15) . . . . ?
N00D C00G C00K S002 0.8(2) . . . . ?
N00D C00G C00K C00H 177.75(15) . . . . ?
N00D C00G C00M C00O -179.33(15) . . . . ?
N00E S001 C00F C00I 83.02(14) . . . . ?
N00E S001 C00F C00J -107.43(14) . . . . ?
N00E S002 C00K C00G -93.46(15) . . . . ?
N00E S002 C00K C00H 89.56(14) . . . . ?
C00F S001 N00E S002 -157.00(9) . . . . ?
C00F S001 N00E F003 80.10(10) . . . . ?
C00F C00I C00L C00P 0.8(2) . . . . ?
C00F C00J C00Q C00P 1.3(3) . . . . ?
C00G C00M C00O C00N 1.5(3) . . . . ?
C00H C00N C00O C00M -1.4(3) . . . . ?
C00I C00F C00J C00Q -1.2(3) . . . . ?
C00I C00L C00P C00Q -0.7(3) . . . . ?
C00J C00F C00I N00C -179.39(15) . . . . ?
C00J C00F C00I C00L 0.2(2) . . . . ?
C00K S002 N00E S001 -47.54(11) . . . . ?
C00K S002 N00E F003 73.87(11) . . . . ?
C00K C00G C00M C00O -0.1(3) . . . . ?
C00K C00H C00N C00O -0.1(3) . . . . ?
C00L C00P C00Q C00J -0.3(3) . . . . ?
C00M C00G C00K S002 -178.32(13) . . . . ?
C00M C00G C00K C00H -1.4(2) . . . . ?
C00N C00H C00K S002 178.63(12) . . . . ?
C00N C00H C00K C00G 1.5(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_4-nsnsnf_auto
_audit_block_doi                 10.5517/ccdc.csd.cc2f02n6
_database_code_depnum_ccdc_archive 'CCDC 2234407'
loop_
_audit_author_name
_audit_author_address
'Kohsuke Aikawa'
;The University of Tokyo
Japan
;
_audit_update_record             
;
2023-05-02 deposited with the CCDC.	2023-06-22 downloaded from the CCDC.
;
_audit_creation_date             2021-11-28
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H8 F N3 O8 S2'
_chemical_formula_sum            'C12 H8 F N3 O8 S2'
_chemical_formula_weight         405.33
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   7.6151(3)
_cell_length_b                   12.0228(4)
_cell_length_c                   17.3608(7)
_cell_angle_alpha                90
_cell_angle_beta                 94.123(4)
_cell_angle_gamma                90
_cell_volume                     1585.35(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4567
_cell_measurement_temperature    169.98(10)
_cell_measurement_theta_max      30.3360
_cell_measurement_theta_min      2.1040
_shelx_estimated_absorpt_T_max   0.961
_shelx_estimated_absorpt_T_min   0.832
_exptl_absorpt_coefficient_mu    0.398
_exptl_absorpt_correction_T_max  0.939
_exptl_absorpt_correction_T_min  0.851
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.99a (Rigaku Oxford Diffraction, 2021)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.698
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             824
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -8 -21 0.0495
-7 -6 -16 0.1773
0 15 -12 0.0756
-11 0 5 0.2456
0 8 21 0.0449
9 4 10 0.1976
9 -5 -14 0.1791
-10 -5 9 0.2096
10 -5 -1 0.1943
0 -15 12 0.0445

_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0154
_diffrn_reflns_av_unetI/netI     0.0202
_diffrn_reflns_Laue_measured_fraction_full 0.952
_diffrn_reflns_Laue_measured_fraction_max 0.939
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7826
_diffrn_reflns_point_group_measured_fraction_full 0.952
_diffrn_reflns_point_group_measured_fraction_max 0.939
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.360
_diffrn_reflns_theta_min         2.062
_diffrn_ambient_temperature      170.15
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.952
_diffrn_measured_fraction_theta_max 0.939
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -13.00 109.00   0.50  120.00    --   20.00  54.00 -60.00  244
  2  ω    -72.00 -37.00   0.50  120.00    --   20.00  54.00   0.00   70
  3  ω     -1.00  25.00   0.50  120.00    --   20.00  54.00   0.00   52
  4  ω     78.00 109.00   0.50  120.00    --   20.00  54.00   0.00   62
  5  ω      4.00  72.00   0.50  120.00    --   20.00  54.00-150.00  136
  6  ω    -35.00 -10.00   0.50  120.00    --   20.00  54.00-180.00   50
  7  ω     69.00  94.00   0.50  120.00    --   20.00  54.00-180.00   50
  8  ω    -57.00 -32.00   0.50  120.00    --   20.00  54.00 -60.00   50
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini II'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2660
_reflns_number_total             3042
_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 1.171.41.99a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.99a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.99a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.367
_refine_diff_density_min         -0.308
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       0.0021(7)
_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   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3042
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0352
_refine_ls_R_factor_gt           0.0287
_refine_ls_restrained_S_all      1.066
_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)+(0.0361P)²+0.6669P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0729
_refine_ls_wR_factor_ref         0.0754
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00H(H00H), C00I(H00I), C00L(H00L), C00M(H00M), C00N(H00N), C00O(H00O),
 C00P(H00P), C00Q(H00Q)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S001 S 0.23585(5) 0.60132(3) 0.60811(2) 0.02364(12) Uani 1 1 d . . . . .
S002 S 0.33219(6) 0.71979(3) 0.75777(2) 0.02541(12) Uani 1 1 d . . . . .
F003 F 0.47094(13) 0.54475(8) 0.70943(6) 0.0320(2) Uani 1 1 d . . . . .
O004 O 0.16104(16) 0.76746(10) 0.75251(7) 0.0335(3) Uani 1 1 d . . . . .
O005 O 0.38147(17) 0.63383(10) 0.56657(7) 0.0350(3) Uani 1 1 d . . . . .
O006 O 0.07733(17) 0.66367(10) 0.60365(7) 0.0336(3) Uani 1 1 d . . . . .
O007 O 0.41541(18) 0.68554(11) 0.82965(7) 0.0361(3) Uani 1 1 d . . . . .
O008 O -0.06969(17) 0.50956(11) 0.70379(8) 0.0382(3) Uani 1 1 d . . . . .
N009 N 0.30252(17) 0.59646(11) 0.70655(8) 0.0228(3) Uani 1 1 d . . . . .
N00A N -0.10645(19) 0.46297(13) 0.64238(9) 0.0310(3) Uani 1 1 d . . . . .
O00B O 0.7647(2) 1.05248(14) 0.53477(9) 0.0544(4) Uani 1 1 d . . . . .
O00C O -0.25436(17) 0.45536(15) 0.61062(10) 0.0561(4) Uani 1 1 d . . . . .
N00D N 0.8255(2) 0.99436(14) 0.58793(10) 0.0388(4) Uani 1 1 d . . . . .
O1 O 0.9817(2) 0.99062(15) 0.60924(11) 0.0630(5) Uani 1 1 d . . . . .
C00F C 0.1954(2) 0.45835(13) 0.59183(9) 0.0217(3) Uani 1 1 d . . . . .
C00G C 0.0360(2) 0.40618(14) 0.60450(9) 0.0235(3) Uani 1 1 d . . . . .
C00H C 0.4090(2) 0.87874(14) 0.65448(10) 0.0282(4) Uani 1 1 d . . . . .
H00H H 0.285356 0.888568 0.645995 0.034 Uiso 1 1 calc R U . . .
C00I C 0.3262(2) 0.39845(14) 0.55867(9) 0.0264(4) Uani 1 1 d . . . . .
H00I H 0.434254 0.433440 0.549015 0.032 Uiso 1 1 calc R U . . .
C00J C 0.4782(2) 0.80030(13) 0.70728(10) 0.0247(4) Uani 1 1 d . . . . .
C00K C 0.7026(2) 0.92411(14) 0.62903(10) 0.0291(4) Uani 1 1 d . . . . .
C00L C 0.5239(2) 0.94201(14) 0.61469(10) 0.0305(4) Uani 1 1 d . . . . .
H00L H 0.481191 0.996460 0.578366 0.037 Uiso 1 1 calc R U . . .
C00M C 0.6586(2) 0.78208(15) 0.72027(11) 0.0335(4) Uani 1 1 d . . . . .
H00M H 0.702215 0.726818 0.755784 0.040 Uiso 1 1 calc R U . . .
C00N C 0.2989(2) 0.28701(15) 0.53954(10) 0.0309(4) Uani 1 1 d . . . . .
H00N H 0.389535 0.245253 0.518221 0.037 Uiso 1 1 calc R U . . .
C00O C 0.0070(2) 0.29678(15) 0.58327(10) 0.0298(4) Uani 1 1 d . . . . .
H00O H -0.103162 0.262593 0.590320 0.036 Uiso 1 1 calc R U . . .
C00P C 0.1396(3) 0.23730(15) 0.55165(10) 0.0329(4) Uani 1 1 d . . . . .
H00P H 0.120965 0.161436 0.538107 0.039 Uiso 1 1 calc R U . . .
C00Q C 0.7725(2) 0.84573(16) 0.68062(11) 0.0352(4) Uani 1 1 d . . . . .
H00Q H 0.896238 0.835904 0.688601 0.042 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S001 O005 1.4204(13) . ?
S001 O006 1.4183(13) . ?
S001 N009 1.7486(14) . ?
S001 C00F 1.7656(16) . ?
S002 O004 1.4207(13) . ?
S002 O007 1.4194(13) . ?
S002 N009 1.7354(14) . ?
S002 C00J 1.7554(17) . ?
F003 N009 1.4228(16) . ?
O008 N00A 1.2190(19) . ?
N00A O00C 1.2214(19) . ?
N00A C00G 1.476(2) . ?
O00B N00D 1.222(2) . ?
N00D O1 1.221(2) . ?
N00D C00K 1.481(2) . ?
C00F C00G 1.397(2) . ?
C00F C00I 1.387(2) . ?
C00G C00O 1.379(2) . ?
C00H H00H 0.9500 . ?
C00H C00J 1.392(2) . ?
C00H C00L 1.381(2) . ?
C00I H00I 0.9500 . ?
C00I C00N 1.392(2) . ?
C00J C00M 1.393(2) . ?
C00K C00L 1.382(2) . ?
C00K C00Q 1.380(3) . ?
C00L H00L 0.9500 . ?
C00M H00M 0.9500 . ?
C00M C00Q 1.377(3) . ?
C00N H00N 0.9500 . ?
C00N C00P 1.382(3) . ?
C00O H00O 0.9500 . ?
C00O C00P 1.383(3) . ?
C00P H00P 0.9500 . ?
C00Q H00Q 0.9500 . ?

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
O005 S001 N009 108.85(7) . . ?
O005 S001 C00F 108.68(8) . . ?
O006 S001 O005 121.29(8) . . ?
O006 S001 N009 104.91(7) . . ?
O006 S001 C00F 111.57(8) . . ?
N009 S001 C00F 99.15(7) . . ?
O004 S002 N009 103.10(7) . . ?
O004 S002 C00J 110.88(8) . . ?
O007 S002 O004 121.54(8) . . ?
O007 S002 N009 103.66(7) . . ?
O007 S002 C00J 109.89(8) . . ?
N009 S002 C00J 106.20(7) . . ?
S002 N009 S001 119.35(8) . . ?
F003 N009 S001 104.28(9) . . ?
F003 N009 S002 105.75(9) . . ?
O008 N00A O00C 125.14(16) . . ?
O008 N00A C00G 118.18(14) . . ?
O00C N00A C00G 116.61(15) . . ?
O00B N00D C00K 118.14(17) . . ?
O1 N00D O00B 123.91(18) . . ?
O1 N00D C00K 117.95(17) . . ?
C00G C00F S001 123.74(13) . . ?
C00I C00F S001 116.71(12) . . ?
C00I C00F C00G 119.33(15) . . ?
C00F C00G N00A 122.48(15) . . ?
C00O C00G N00A 116.83(15) . . ?
C00O C00G C00F 120.68(16) . . ?
C00J C00H H00H 120.7 . . ?
C00L C00H H00H 120.7 . . ?
C00L C00H C00J 118.63(16) . . ?
C00F C00I H00I 120.0 . . ?
C00F C00I C00N 119.95(16) . . ?
C00N C00I H00I 120.0 . . ?
C00H C00J S002 118.63(13) . . ?
C00H C00J C00M 122.34(17) . . ?
C00M C00J S002 119.01(13) . . ?
C00L C00K N00D 118.19(16) . . ?
C00Q C00K N00D 118.32(17) . . ?
C00Q C00K C00L 123.48(17) . . ?
C00H C00L C00K 118.35(16) . . ?
C00H C00L H00L 120.8 . . ?
C00K C00L H00L 120.8 . . ?
C00J C00M H00M 120.6 . . ?
C00Q C00M C00J 118.73(17) . . ?
C00Q C00M H00M 120.6 . . ?
C00I C00N H00N 120.1 . . ?
C00P C00N C00I 119.84(17) . . ?
C00P C00N H00N 120.1 . . ?
C00G C00O H00O 120.3 . . ?
C00G C00O C00P 119.45(16) . . ?
C00P C00O H00O 120.3 . . ?
C00N C00P C00O 120.71(16) . . ?
C00N C00P H00P 119.6 . . ?
C00O C00P H00P 119.6 . . ?
C00K C00Q H00Q 120.8 . . ?
C00M C00Q C00K 118.45(17) . . ?
C00M C00Q H00Q 120.8 . . ?

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
S001 C00F C00G N00A -8.1(2) . . . . ?
S001 C00F C00G C00O 173.41(13) . . . . ?
S001 C00F C00I C00N -175.87(13) . . . . ?
S002 C00J C00M C00Q -179.83(14) . . . . ?
O004 S002 N009 S001 62.80(10) . . . . ?
O004 S002 N009 F003 179.71(9) . . . . ?
O004 S002 C00J C00H -15.97(16) . . . . ?
O004 S002 C00J C00M 165.26(13) . . . . ?
O005 S001 N009 S002 75.19(10) . . . . ?
O005 S001 N009 F003 -42.49(11) . . . . ?
O005 S001 C00F C00G -160.82(13) . . . . ?
O005 S001 C00F C00I 13.77(15) . . . . ?
O006 S001 N009 S002 -56.02(10) . . . . ?
O006 S001 N009 F003 -173.70(9) . . . . ?
O006 S001 C00F C00G -24.50(16) . . . . ?
O006 S001 C00F C00I 150.09(12) . . . . ?
O007 S002 N009 S001 -169.67(9) . . . . ?
O007 S002 N009 F003 -52.75(11) . . . . ?
O007 S002 C00J C00H -153.14(13) . . . . ?
O007 S002 C00J C00M 28.09(16) . . . . ?
O008 N00A C00G C00F -50.8(2) . . . . ?
O008 N00A C00G C00O 127.70(17) . . . . ?
N009 S001 C00F C00G 85.61(14) . . . . ?
N009 S001 C00F C00I -99.80(13) . . . . ?
N009 S002 C00J C00H 95.35(14) . . . . ?
N009 S002 C00J C00M -83.42(15) . . . . ?
N00A C00G C00O C00P -176.27(15) . . . . ?
O00B N00D C00K C00L -11.2(2) . . . . ?
O00B N00D C00K C00Q 169.96(17) . . . . ?
O00C N00A C00G C00F 132.04(18) . . . . ?
O00C N00A C00G C00O -49.4(2) . . . . ?
N00D C00K C00L C00H -178.25(15) . . . . ?
N00D C00K C00Q C00M 178.49(16) . . . . ?
O1 N00D C00K C00L 168.83(18) . . . . ?
O1 N00D C00K C00Q -10.0(3) . . . . ?
C00F S001 N009 S002 -171.38(9) . . . . ?
C00F S001 N009 F003 70.95(10) . . . . ?
C00F C00G C00O C00P 2.3(3) . . . . ?
C00F C00I C00N C00P 1.8(3) . . . . ?
C00G C00F C00I C00N -1.0(2) . . . . ?
C00G C00O C00P C00N -1.5(3) . . . . ?
C00H C00J C00M C00Q 1.4(3) . . . . ?
C00I C00F C00G N00A 177.44(14) . . . . ?
C00I C00F C00G C00O -1.0(2) . . . . ?
C00I C00N C00P C00O -0.6(3) . . . . ?
C00J S002 N009 S001 -53.87(10) . . . . ?
C00J S002 N009 F003 63.04(10) . . . . ?
C00J C00H C00L C00K 0.2(3) . . . . ?
C00J C00M C00Q C00K -0.7(3) . . . . ?
C00L C00H C00J S002 -179.93(13) . . . . ?
C00L C00H C00J C00M -1.2(3) . . . . ?
C00L C00K C00Q C00M -0.3(3) . . . . ?
C00Q C00K C00L C00H 0.5(3) . . . . ?

_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
;
####################################################################### 
# 
# 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_nsbznf_auto
_audit_block_doi                 10.5517/ccdc.csd.cc2f02k3
_database_code_depnum_ccdc_archive 'CCDC 2234404'
loop_
_audit_author_name
_audit_author_address
'Kohsuke Aikawa'
;The University of Tokyo
Japan
;
_audit_update_record             
;
2023-05-02 deposited with the CCDC.	2023-06-22 downloaded from the CCDC.
;
_audit_creation_date             2022-05-06
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H9 F N2 O5 S'
_chemical_formula_sum            'C13 H9 F N2 O5 S'
_chemical_formula_weight         324.28
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   7.0221(3)
_cell_length_b                   7.3175(4)
_cell_length_c                   13.1378(7)
_cell_angle_alpha                89.555(4)
_cell_angle_beta                 88.085(4)
_cell_angle_gamma                88.797(4)
_cell_volume                     674.53(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5281
_cell_measurement_temperature    169.99(10)
_cell_measurement_theta_max      30.5510
_cell_measurement_theta_min      2.7670
_shelx_estimated_absorpt_T_max   0.929
_shelx_estimated_absorpt_T_min   0.849
_exptl_absorpt_coefficient_mu    0.279
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90842
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.99a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.597
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       cube
_exptl_crystal_F_000             332
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.609
_exptl_crystal_size_mid          0.343
_exptl_crystal_size_min          0.269
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0213
_diffrn_reflns_av_unetI/netI     0.0253
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7601
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.369
_diffrn_reflns_theta_min         2.784
_diffrn_ambient_temperature      170.15
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.993
_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     24.00  81.00   0.50    3.15    --   20.00  54.00-150.00  114
  2  ω    -73.00 109.00   0.50    3.15    --   20.00  54.00   0.00  364
  3  ω    -72.00  87.00   0.50    3.15    --   20.00  54.00 -60.00  318
  4  ω    -70.00 -15.00   0.50    3.15    --   20.00  54.00  60.00  110
  5  ω     23.00  51.00   0.50    3.15    --   20.00  54.00  60.00   56
  6  ω    -50.00 -25.00   0.50    3.15    --   20.00  54.00 -90.00   50
  7  ω     -6.00  19.00   0.50    3.15    --   20.00  54.00 -90.00   50
  8  ω    -68.00 -20.00   0.50    3.15    --   20.00  54.00 150.00   96
  9  ω    -74.00 -39.00   0.50    3.15    --   20.00  54.00-120.00   70
 10  ω    -20.00   5.00   0.50    3.15    --   20.00  54.00-180.00   50
 11  ω     42.00  67.00   0.50    3.15    --   20.00  54.00-180.00   50
 12  ω    -68.00   6.00   0.50    3.15    --   20.00  54.00 120.00  148
 13  ω     53.00  78.00   0.50    3.15    --   20.00  54.00 120.00   50
 14  ω    -23.00   2.00   0.50    3.15    --   20.00  54.00-150.00   50
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini II'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2416
_reflns_number_total             2732
_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 1.171.41.99a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.99a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.99a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         1.347
_refine_diff_density_min         -0.429
_refine_diff_density_rms         0.072
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2732
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0518
_refine_ls_R_factor_gt           0.0466
_refine_ls_restrained_S_all      1.085
_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)+(0.0726P)²+0.4467P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1244
_refine_ls_wR_factor_ref         0.1283
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00C(H00C), C00F(H00F), C00G(H00G), C00H(H00H), C00I(H00I), C00J(H00J),
 C00K(H00K), C00L(H00L), C00M(H00M)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S001 S 0.63126(7) 0.38296(6) 0.22326(4) 0.01959(17) Uani 1 1 d . . . . .
F002 F 0.82606(18) 0.39298(17) 0.06295(9) 0.0268(3) Uani 1 1 d . . . . .
O003 O 1.0421(2) 0.6071(2) 0.14793(12) 0.0286(4) Uani 1 1 d . . . . .
O004 O 0.6516(2) 0.3264(2) 0.32584(11) 0.0271(4) Uani 1 1 d . . . . .
O005 O 0.5661(2) 0.5629(2) 0.19767(13) 0.0308(4) Uani 1 1 d . . . . .
O006 O 0.5072(3) -0.0987(2) 0.34187(14) 0.0433(5) Uani 1 1 d . . . . .
O007 O 0.7651(2) -0.0489(2) 0.24974(15) 0.0416(5) Uani 1 1 d . . . . .
N008 N 0.8560(2) 0.3498(2) 0.16688(12) 0.0198(4) Uani 1 1 d . . . . .
N009 N 0.5930(3) -0.0396(2) 0.26628(15) 0.0292(4) Uani 1 1 d . . . . .
C00A C 0.9968(3) 0.4817(3) 0.20204(16) 0.0221(4) Uani 1 1 d . . . . .
C00B C 0.4940(3) 0.2270(3) 0.15706(15) 0.0188(4) Uani 1 1 d . . . . .
C00C C 0.3829(3) 0.2962(3) 0.07953(16) 0.0220(4) Uani 1 1 d . . . . .
H00C H 0.391008 0.421244 0.060261 0.026 Uiso 1 1 calc R U . . .
C00D C 1.0760(3) 0.4344(3) 0.30099(16) 0.0230(4) Uani 1 1 d . . . . .
C00E C 0.4760(3) 0.0444(3) 0.18651(16) 0.0213(4) Uani 1 1 d . . . . .
C00F C 0.2596(3) 0.1826(3) 0.03001(17) 0.0248(5) Uani 1 1 d . . . . .
H00F H 0.187851 0.228346 -0.025025 0.030 Uiso 1 1 calc R U . . .
C00G C 0.2424(3) 0.0022(3) 0.06156(18) 0.0259(5) Uani 1 1 d . . . . .
H00G H 0.156419 -0.074634 0.028683 0.031 Uiso 1 1 calc R U . . .
C00H C 0.3490(3) -0.0674(3) 0.14048(18) 0.0250(5) Uani 1 1 d . . . . .
H00H H 0.334811 -0.190421 0.162581 0.030 Uiso 1 1 calc R U . . .
C00I C 1.1550(3) 0.5773(3) 0.35508(17) 0.0281(5) Uani 1 1 d . . . . .
H00I H 1.149701 0.698760 0.329169 0.034 Uiso 1 1 calc R U . . .
C00J C 1.0847(3) 0.2555(3) 0.33807(18) 0.0298(5) Uani 1 1 d . . . . .
H00J H 1.031178 0.158800 0.301367 0.036 Uiso 1 1 calc R U . . .
C00K C 1.2404(3) 0.5400(4) 0.44627(18) 0.0366(6) Uani 1 1 d . . . . .
H00K H 1.293189 0.636207 0.483603 0.044 Uiso 1 1 calc R U . . .
C00L C 1.1729(4) 0.2207(4) 0.4296(2) 0.0385(6) Uani 1 1 d . . . . .
H00L H 1.180995 0.099390 0.455558 0.046 Uiso 1 1 calc R U . . .
C00M C 1.2492(3) 0.3634(4) 0.48323(19) 0.0399(6) Uani 1 1 d . . . . .
H00M H 1.308181 0.338828 0.546068 0.048 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
S001 O004 1.4176(16) . ?
S001 O005 1.4266(16) . ?
S001 N008 1.7340(18) . ?
S001 C00B 1.762(2) . ?
F002 N008 1.4205(19) . ?
O003 C00A 1.198(3) . ?
O006 N009 1.225(3) . ?
O007 N009 1.222(3) . ?
N008 C00A 1.483(3) . ?
N009 C00E 1.476(3) . ?
C00A C00D 1.467(3) . ?
C00B C00C 1.390(3) . ?
C00B C00E 1.395(3) . ?
C00C H00C 0.9500 . ?
C00C C00F 1.393(3) . ?
C00D C00I 1.402(3) . ?
C00D C00J 1.395(3) . ?
C00E C00H 1.380(3) . ?
C00F H00F 0.9500 . ?
C00F C00G 1.387(3) . ?
C00G H00G 0.9500 . ?
C00G C00H 1.387(3) . ?
C00H H00H 0.9500 . ?
C00I H00I 0.9500 . ?
C00I C00K 1.381(3) . ?
C00J H00J 0.9500 . ?
C00J C00L 1.390(3) . ?
C00K H00K 0.9500 . ?
C00K C00M 1.377(4) . ?
C00L H00L 0.9500 . ?
C00L C00M 1.391(4) . ?
C00M H00M 0.9500 . ?

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
O004 S001 O005 121.69(10) . . ?
O004 S001 N008 104.61(9) . . ?
O004 S001 C00B 110.85(9) . . ?
O005 S001 N008 107.90(9) . . ?
O005 S001 C00B 107.76(10) . . ?
N008 S001 C00B 102.22(9) . . ?
F002 N008 S001 102.86(11) . . ?
F002 N008 C00A 106.22(14) . . ?
C00A N008 S001 112.98(13) . . ?
O006 N009 C00E 116.65(19) . . ?
O007 N009 O006 126.0(2) . . ?
O007 N009 C00E 117.30(19) . . ?
O003 C00A N008 119.56(19) . . ?
O003 C00A C00D 126.46(19) . . ?
C00D C00A N008 113.87(17) . . ?
C00C C00B S001 117.47(15) . . ?
C00C C00B C00E 119.18(18) . . ?
C00E C00B S001 122.94(16) . . ?
C00B C00C H00C 119.9 . . ?
C00B C00C C00F 120.15(19) . . ?
C00F C00C H00C 119.9 . . ?
C00I C00D C00A 116.71(19) . . ?
C00J C00D C00A 122.6(2) . . ?
C00J C00D C00I 120.6(2) . . ?
C00B C00E N009 122.15(18) . . ?
C00H C00E N009 116.77(18) . . ?
C00H C00E C00B 121.07(19) . . ?
C00C C00F H00F 120.2 . . ?
C00G C00F C00C 119.6(2) . . ?
C00G C00F H00F 120.2 . . ?
C00F C00G H00G 119.6 . . ?
C00H C00G C00F 120.83(19) . . ?
C00H C00G H00G 119.6 . . ?
C00E C00H C00G 119.13(19) . . ?
C00E C00H H00H 120.4 . . ?
C00G C00H H00H 120.4 . . ?
C00D C00I H00I 120.2 . . ?
C00K C00I C00D 119.5(2) . . ?
C00K C00I H00I 120.2 . . ?
C00D C00J H00J 120.5 . . ?
C00L C00J C00D 118.9(2) . . ?
C00L C00J H00J 120.5 . . ?
C00I C00K H00K 119.9 . . ?
C00M C00K C00I 120.1(2) . . ?
C00M C00K H00K 119.9 . . ?
C00J C00L H00L 120.0 . . ?
C00J C00L C00M 120.1(2) . . ?
C00M C00L H00L 120.0 . . ?
C00K C00M C00L 120.7(2) . . ?
C00K C00M H00M 119.6 . . ?
C00L C00M H00M 119.6 . . ?

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
S001 N008 C00A O003 -103.4(2) . . . . ?
S001 N008 C00A C00D 80.26(19) . . . . ?
S001 C00B C00C C00F -174.78(16) . . . . ?
S001 C00B C00E N009 -9.2(3) . . . . ?
S001 C00B C00E C00H 171.91(16) . . . . ?
F002 N008 C00A O003 8.6(3) . . . . ?
F002 N008 C00A C00D -167.70(16) . . . . ?
O003 C00A C00D C00I 25.5(3) . . . . ?
O003 C00A C00D C00J -150.6(2) . . . . ?
O004 S001 N008 F002 175.27(10) . . . . ?
O004 S001 N008 C00A -70.64(15) . . . . ?
O004 S001 C00B C00C 148.53(16) . . . . ?
O004 S001 C00B C00E -24.0(2) . . . . ?
O005 S001 N008 F002 -53.83(13) . . . . ?
O005 S001 N008 C00A 60.26(15) . . . . ?
O005 S001 C00B C00C 13.11(19) . . . . ?
O005 S001 C00B C00E -159.44(17) . . . . ?
O006 N009 C00E C00B 118.9(2) . . . . ?
O006 N009 C00E C00H -62.2(3) . . . . ?
O007 N009 C00E C00B -63.3(3) . . . . ?
O007 N009 C00E C00H 115.6(2) . . . . ?
N008 S001 C00B C00C -100.45(17) . . . . ?
N008 S001 C00B C00E 87.00(18) . . . . ?
N008 C00A C00D C00I -158.50(18) . . . . ?
N008 C00A C00D C00J 25.4(3) . . . . ?
N009 C00E C00H C00G -176.83(19) . . . . ?
C00A C00D C00I C00K -176.8(2) . . . . ?
C00A C00D C00J C00L 176.0(2) . . . . ?
C00B S001 N008 F002 59.62(12) . . . . ?
C00B S001 N008 C00A 173.71(14) . . . . ?
C00B C00C C00F C00G 2.8(3) . . . . ?
C00B C00E C00H C00G 2.1(3) . . . . ?
C00C C00B C00E N009 178.32(19) . . . . ?
C00C C00B C00E C00H -0.5(3) . . . . ?
C00C C00F C00G C00H -1.3(3) . . . . ?
C00D C00I C00K C00M 0.5(3) . . . . ?
C00D C00J C00L C00M 0.6(4) . . . . ?
C00E C00B C00C C00F -1.9(3) . . . . ?
C00F C00G C00H C00E -1.2(3) . . . . ?
C00I C00D C00J C00L 0.0(3) . . . . ?
C00I C00K C00M C00L 0.0(4) . . . . ?
C00J C00D C00I C00K -0.6(3) . . . . ?
C00J C00L C00M C00K -0.6(4) . . . . ?

_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
;
####################################################################### 
# 
# 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_nsnhf_auto
_audit_block_doi                 10.5517/ccdc.csd.cc2fvvqw
_database_code_depnum_ccdc_archive 'CCDC 2260139'
loop_
_audit_author_name
_audit_author_address
'Kohsuke Aikawa'
;The University of Tokyo
Japan
;
_audit_update_record             
;
2023-05-02 deposited with the CCDC.	2023-06-22 downloaded from the CCDC.
;
_audit_creation_date             2021-06-14
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C6 H5 F N2 O4 S'
_chemical_formula_sum            'C6 H5 F N2 O4 S'
_chemical_formula_weight         220.18
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   8.0042(7)
_cell_length_b                   16.3141(10)
_cell_length_c                   7.3230(6)
_cell_angle_alpha                90
_cell_angle_beta                 116.252(11)
_cell_angle_gamma                90
_cell_volume                     857.62(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2941
_cell_measurement_temperature    170.00(10)
_cell_measurement_theta_max      30.4580
_cell_measurement_theta_min      2.4890
_shelx_estimated_absorpt_T_max   0.934
_shelx_estimated_absorpt_T_min   0.875
_exptl_absorpt_coefficient_mu    0.385
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98917
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.99a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.705
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             448
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.357
_exptl_crystal_size_mid          0.303
_exptl_crystal_size_min          0.179
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0207
_diffrn_reflns_av_unetI/netI     0.0325
_diffrn_reflns_Laue_measured_fraction_full 0.896
_diffrn_reflns_Laue_measured_fraction_max 0.824
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            5302
_diffrn_reflns_point_group_measured_fraction_full 0.896
_diffrn_reflns_point_group_measured_fraction_max 0.824
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.561
_diffrn_reflns_theta_min         2.497
_diffrn_ambient_temperature      170.15
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.896
_diffrn_measured_fraction_theta_max 0.824
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     33.00  59.00   0.50    5.00    --   20.00  54.00-180.00   52
  2  ω    -52.00  85.00   0.50    5.00    --   20.00  54.00 -90.00  274
  3  ω    -67.00  51.00   0.50    5.00    --   20.00  54.00 150.00  236
  4  ω     64.00  89.00   0.50    5.00    --   20.00  54.00-120.00   50
  5  ω    -24.00  21.00   0.50    5.00    --   20.00  54.00-180.00   90
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini II'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1751
_reflns_number_total             2168
_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 1.171.41.99a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.99a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.99a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.672
_refine_diff_density_min         -0.651
_refine_diff_density_rms         0.066
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         2168
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0525
_refine_ls_R_factor_gt           0.0412
_refine_ls_restrained_S_all      1.049
_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)+(0.0629P)²+0.3022P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1113
_refine_ls_wR_factor_ref         0.1184
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Riding coordinates:
 N008(H008)
2.b Aromatic/amide H refined with riding coordinates:
 C00A(H00A), C00C(H00C), C00D(H00D), C00E(H00E)
;
_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
S001 S 0.85460(6) 0.38039(3) 0.25452(7) 0.02469(15) Uani 1 1 d . . . . .
F002 F 0.9559(2) 0.35895(9) 0.62557(18) 0.0499(4) Uani 1 1 d . . . . .
O003 O 0.9741(2) 0.44977(9) 0.3077(2) 0.0322(4) Uani 1 1 d . . . . .
O004 O 0.8309(2) 0.33128(9) 0.0836(2) 0.0368(4) Uani 1 1 d . . . . .
O005 O 0.5887(2) 0.23831(9) 0.1797(3) 0.0465(5) Uani 1 1 d . . . . .
O006 O 0.3341(2) 0.26479(11) -0.0880(3) 0.0552(6) Uani 1 1 d . . . . .
N007 N 0.4641(2) 0.28468(10) 0.0720(3) 0.0321(4) Uani 1 1 d . . . . .
N008 N 0.9438(3) 0.31570(11) 0.4517(3) 0.0346(4) Uani 1 1 d . . . . .
H008 H 1.047497 0.291373 0.467674 0.042 Uiso 1 1 d R U . . .
C009 C 0.4694(3) 0.36974(11) 0.1408(3) 0.0246(4) Uani 1 1 d . . . . .
C00A C 0.6283(3) 0.49485(11) 0.2909(3) 0.0248(4) Uani 1 1 d . . . . .
H00A H 0.738838 0.526793 0.349521 0.030 Uiso 1 1 calc R U . . .
C00B C 0.6352(2) 0.41438(11) 0.2295(2) 0.0212(4) Uani 1 1 d . . . . .
C00C C 0.4597(3) 0.52828(12) 0.2663(3) 0.0308(5) Uani 1 1 d . . . . .
H00C H 0.455924 0.582778 0.309974 0.037 Uiso 1 1 calc R U . . .
C00D C 0.3015(3) 0.40313(13) 0.1146(3) 0.0313(5) Uani 1 1 d . . . . .
H00D H 0.190020 0.371914 0.053408 0.038 Uiso 1 1 calc R U . . .
C00E C 0.2980(3) 0.48277(13) 0.1788(3) 0.0317(5) Uani 1 1 d . . . . .
H00E H 0.183545 0.506161 0.162476 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
S001 O003 1.4207(14) . ?
S001 O004 1.4265(15) . ?
S001 N008 1.6723(17) . ?
S001 C00B 1.772(2) . ?
F002 N008 1.421(2) . ?
O005 N007 1.222(2) . ?
O006 N007 1.218(2) . ?
N007 C009 1.470(2) . ?
N008 H008 0.8800 . ?
C009 C00B 1.397(2) . ?
C009 C00D 1.382(3) . ?
C00A H00A 0.9500 . ?
C00A C00B 1.397(3) . ?
C00A C00C 1.391(3) . ?
C00C H00C 0.9500 . ?
C00C C00E 1.380(3) . ?
C00D H00D 0.9500 . ?
C00D C00E 1.386(3) . ?
C00E H00E 0.9500 . ?

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
O003 S001 O004 119.99(10) . . ?
O003 S001 N008 106.72(9) . . ?
O003 S001 C00B 107.19(9) . . ?
O004 S001 N008 104.10(9) . . ?
O004 S001 C00B 110.12(9) . . ?
N008 S001 C00B 108.17(9) . . ?
O005 N007 C009 118.15(16) . . ?
O006 N007 O005 124.21(19) . . ?
O006 N007 C009 117.63(17) . . ?
S001 N008 H008 114.6 . . ?
F002 N008 S001 107.12(12) . . ?
F002 N008 H008 114.7 . . ?
C00B C009 N007 121.90(18) . . ?
C00D C009 N007 116.46(17) . . ?
C00D C009 C00B 121.63(18) . . ?
C00B C00A H00A 120.0 . . ?
C00C C00A H00A 120.0 . . ?
C00C C00A C00B 120.05(18) . . ?
C009 C00B S001 125.40(15) . . ?
C00A C00B S001 116.06(14) . . ?
C00A C00B C009 118.36(18) . . ?
C00A C00C H00C 119.8 . . ?
C00E C00C C00A 120.42(19) . . ?
C00E C00C H00C 119.8 . . ?
C009 C00D H00D 120.4 . . ?
C009 C00D C00E 119.10(19) . . ?
C00E C00D H00D 120.4 . . ?
C00C C00E C00D 120.4(2) . . ?
C00C C00E H00E 119.8 . . ?
C00D C00E H00E 119.8 . . ?

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
O003 S001 N008 F002 57.14(15) . . . . ?
O003 S001 C00B C009 166.69(15) . . . . ?
O003 S001 C00B C00A -8.35(16) . . . . ?
O004 S001 N008 F002 -175.01(13) . . . . ?
O004 S001 C00B C009 34.58(18) . . . . ?
O004 S001 C00B C00A -140.46(14) . . . . ?
O005 N007 C009 C00B 41.2(3) . . . . ?
O005 N007 C009 C00D -138.3(2) . . . . ?
O006 N007 C009 C00B -139.6(2) . . . . ?
O006 N007 C009 C00D 40.9(3) . . . . ?
N007 C009 C00B S001 5.1(3) . . . . ?
N007 C009 C00B C00A -179.94(17) . . . . ?
N007 C009 C00D C00E 179.21(18) . . . . ?
N008 S001 C00B C009 -78.58(17) . . . . ?
N008 S001 C00B C00A 106.38(15) . . . . ?
C009 C00D C00E C00C 0.5(3) . . . . ?
C00A C00C C00E C00D 0.1(3) . . . . ?
C00B S001 N008 F002 -57.90(14) . . . . ?
C00B C009 C00D C00E -0.3(3) . . . . ?
C00B C00A C00C C00E -0.9(3) . . . . ?
C00C C00A C00B S001 176.45(14) . . . . ?
C00C C00A C00B C009 1.0(3) . . . . ?
C00D C009 C00B S001 -175.41(14) . . . . ?
C00D C009 C00B C00A -0.5(3) . . . . ?

_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
;
####################################################################### 
# 
# 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_20210311_nsmsnf_auto
_audit_block_doi                 10.5517/ccdc.csd.cc2f02l4
_database_code_depnum_ccdc_archive 'CCDC 2234405'
loop_
_audit_author_name
_audit_author_address
'Kohsuke Aikawa'
;The University of Tokyo
Japan
;
_audit_update_record             
;
2023-05-02 deposited with the CCDC.	2023-06-22 downloaded from the CCDC.
;
_audit_creation_date             2021-03-12
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C7 H7 F N2 O6 S2'
_chemical_formula_sum            'C7 H7 F N2 O6 S2'
_chemical_formula_weight         298.27
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   13.5187(3)
_cell_length_b                   19.0911(5)
_cell_length_c                   8.8331(2)
_cell_angle_alpha                90
_cell_angle_beta                 95.077(2)
_cell_angle_gamma                90
_cell_volume                     2270.76(9)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    54331
_cell_measurement_temperature    170.15
_cell_measurement_theta_max      30.4330
_cell_measurement_theta_min      2.2170
_shelx_estimated_absorpt_T_max   0.897
_shelx_estimated_absorpt_T_min   0.876
_exptl_absorpt_coefficient_mu    0.505
_exptl_absorpt_correction_T_max  0.877
_exptl_absorpt_correction_T_min  0.855
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.99a (Rigaku Oxford Diffraction, 2021)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.745
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1216
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0336
_diffrn_reflns_av_unetI/netI     0.0339
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            7372
_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         26.370
_diffrn_reflns_theta_min         1.851
_diffrn_ambient_temperature      170.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2072
_reflns_number_total             2318
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.509
_refine_diff_density_min         -0.382
_refine_diff_density_rms         0.070
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2318
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0398
_refine_ls_R_factor_gt           0.0353
_refine_ls_restrained_S_all      1.038
_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)+(0.0544P)²+2.2046P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0961
_refine_ls_wR_factor_ref         0.0998
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00F(H00F), C00G(H00G), C00H(H00H), C00I(H00I)
2.b Idealised Me refined as rotating group:
 C00E(H00A,H00B,H00C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S001 S 0.34697(3) 0.58876(2) 0.34454(5) 0.02783(15) Uani 1 1 d . . . . .
S002 S 0.13818(3) 0.54877(2) 0.41059(5) 0.02683(15) Uani 1 1 d . . . . .
F003 F 0.29059(9) 0.56119(7) 0.60062(13) 0.0380(3) Uani 1 1 d . . . . .
O004 O 0.08276(10) 0.56213(7) 0.53745(17) 0.0342(3) Uani 1 1 d . . . . .
O005 O 0.30664(11) 0.61196(8) 0.19976(15) 0.0372(4) Uani 1 1 d . . . . .
O006 O 0.10978(10) 0.57709(8) 0.26468(17) 0.0377(4) Uani 1 1 d . . . . .
O007 O 0.24530(11) 0.73293(9) 0.33931(19) 0.0436(4) Uani 1 1 d . . . . .
O008 O 0.39495(11) 0.52264(8) 0.3615(2) 0.0413(4) Uani 1 1 d . . . . .
O009 O 0.34362(13) 0.80628(8) 0.24104(19) 0.0450(4) Uani 1 1 d . . . . .
N00A N 0.32740(12) 0.75650(9) 0.32338(19) 0.0312(4) Uani 1 1 d . . . . .
N00B N 0.25032(12) 0.59137(8) 0.46091(17) 0.0271(4) Uani 1 1 d . . . . .
C00C C 0.42505(13) 0.65315(10) 0.4350(2) 0.0253(4) Uani 1 1 d . . . . .
C00D C 0.41363(13) 0.72547(10) 0.4123(2) 0.0272(4) Uani 1 1 d . . . . .
C00E C 0.16446(16) 0.45925(10) 0.4040(2) 0.0325(4) Uani 1 1 d . . . . .
H00A H 0.197451 0.444313 0.501987 0.049 Uiso 1 1 calc R U . . .
H00B H 0.208205 0.450232 0.323466 0.049 Uiso 1 1 calc R U . . .
H00C H 0.102468 0.433003 0.383006 0.049 Uiso 1 1 calc R U . . .
C00F C 0.50765(14) 0.62892(11) 0.5251(2) 0.0317(4) Uani 1 1 d . . . . .
H00F H 0.517082 0.580026 0.540261 0.038 Uiso 1 1 calc R U . . .
C00G C 0.48306(15) 0.77162(11) 0.4776(2) 0.0345(5) Uani 1 1 d . . . . .
H00G H 0.475597 0.820492 0.459842 0.041 Uiso 1 1 calc R U . . .
C00H C 0.56398(15) 0.74666(12) 0.5696(3) 0.0384(5) Uani 1 1 d . . . . .
H00H H 0.611047 0.778601 0.616645 0.046 Uiso 1 1 calc R U . . .
C00I C 0.57626(15) 0.67586(12) 0.5929(2) 0.0366(5) Uani 1 1 d . . . . .
H00I H 0.631910 0.659051 0.655701 0.044 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
S001 O005 1.4162(15) . ?
S001 O008 1.4211(16) . ?
S001 N00B 1.7331(17) . ?
S001 C00C 1.7650(19) . ?
S002 O004 1.4250(14) . ?
S002 O006 1.4188(15) . ?
S002 N00B 1.7430(16) . ?
S002 C00E 1.748(2) . ?
F003 N00B 1.4256(19) . ?
O007 N00A 1.217(2) . ?
O009 N00A 1.228(2) . ?
N00A C00D 1.471(2) . ?
C00C C00D 1.402(3) . ?
C00C C00F 1.392(3) . ?
C00D C00G 1.376(3) . ?
C00E H00A 0.9800 . ?
C00E H00B 0.9800 . ?
C00E H00C 0.9800 . ?
C00F H00F 0.9500 . ?
C00F C00I 1.387(3) . ?
C00G H00G 0.9500 . ?
C00G C00H 1.388(3) . ?
C00H H00H 0.9500 . ?
C00H C00I 1.375(3) . ?
C00I H00I 0.9500 . ?

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
O005 S001 O008 120.58(10) . . ?
O005 S001 N00B 106.05(8) . . ?
O005 S001 C00C 110.99(9) . . ?
O008 S001 N00B 108.91(9) . . ?
O008 S001 C00C 108.76(9) . . ?
N00B S001 C00C 99.40(8) . . ?
O004 S002 N00B 102.82(8) . . ?
O004 S002 C00E 108.88(9) . . ?
O006 S002 O004 121.82(9) . . ?
O006 S002 N00B 102.31(8) . . ?
O006 S002 C00E 112.46(10) . . ?
N00B S002 C00E 106.86(9) . . ?
O007 N00A O009 124.53(17) . . ?
O007 N00A C00D 118.49(16) . . ?
O009 N00A C00D 116.94(17) . . ?
S001 N00B S002 121.31(9) . . ?
F003 N00B S001 104.57(11) . . ?
F003 N00B S002 106.80(11) . . ?
C00D C00C S001 124.55(14) . . ?
C00F C00C S001 116.43(15) . . ?
C00F C00C C00D 118.81(17) . . ?
C00C C00D N00A 123.04(17) . . ?
C00G C00D N00A 116.41(17) . . ?
C00G C00D C00C 120.52(18) . . ?
S002 C00E H00A 109.5 . . ?
S002 C00E H00B 109.5 . . ?
S002 C00E H00C 109.5 . . ?
H00A C00E H00B 109.5 . . ?
H00A C00E H00C 109.5 . . ?
H00B C00E H00C 109.5 . . ?
C00C C00F H00F 119.9 . . ?
C00I C00F C00C 120.28(19) . . ?
C00I C00F H00F 119.9 . . ?
C00D C00G H00G 120.0 . . ?
C00D C00G C00H 119.91(19) . . ?
C00H C00G H00G 120.0 . . ?
C00G C00H H00H 119.9 . . ?
C00I C00H C00G 120.24(19) . . ?
C00I C00H H00H 119.9 . . ?
C00F C00I H00I 119.9 . . ?
C00H C00I C00F 120.21(19) . . ?
C00H C00I H00I 119.9 . . ?

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
S001 C00C C00D N00A 7.6(3) . . . . ?
S001 C00C C00D C00G -174.36(15) . . . . ?
S001 C00C C00F C00I 176.04(16) . . . . ?
O004 S002 N00B S001 178.08(10) . . . . ?
O004 S002 N00B F003 58.66(13) . . . . ?
O005 S001 N00B S002 53.83(13) . . . . ?
O005 S001 N00B F003 174.34(11) . . . . ?
O005 S001 C00C C00D 29.46(19) . . . . ?
O005 S001 C00C C00F -145.16(15) . . . . ?
O006 S002 N00B S001 -54.82(12) . . . . ?
O006 S002 N00B F003 -174.24(11) . . . . ?
O007 N00A C00D C00C 41.6(3) . . . . ?
O007 N00A C00D C00G -136.5(2) . . . . ?
O008 S001 N00B S002 -77.33(12) . . . . ?
O008 S001 N00B F003 43.18(13) . . . . ?
O008 S001 C00C C00D 164.37(16) . . . . ?
O008 S001 C00C C00F -10.26(18) . . . . ?
O009 N00A C00D C00C -140.54(19) . . . . ?
O009 N00A C00D C00G 41.4(3) . . . . ?
N00A C00D C00G C00H 176.73(19) . . . . ?
N00B S001 C00C C00D -81.86(17) . . . . ?
N00B S001 C00C C00F 103.52(15) . . . . ?
C00C S001 N00B S002 169.01(10) . . . . ?
C00C S001 N00B F003 -70.49(12) . . . . ?
C00C C00D C00G C00H -1.4(3) . . . . ?
C00C C00F C00I C00H -1.0(3) . . . . ?
C00D C00C C00F C00I 1.1(3) . . . . ?
C00D C00G C00H C00I 1.5(3) . . . . ?
C00E S002 N00B S001 63.52(13) . . . . ?
C00E S002 N00B F003 -55.90(14) . . . . ?
C00F C00C C00D N00A -177.88(17) . . . . ?
C00F C00C C00D C00G 0.1(3) . . . . ?
C00G C00H C00I C00F -0.2(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_nsbsnf_auto
_audit_block_doi                 10.5517/ccdc.csd.cc2f02j2
_database_code_depnum_ccdc_archive 'CCDC 2234403'
loop_
_audit_author_name
_audit_author_address
'Kohsuke Aikawa'
;The University of Tokyo
Japan
;
_audit_update_record             
;
2023-05-02 deposited with the CCDC.	2023-06-22 downloaded from the CCDC.
;
_audit_creation_date             2021-07-20
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H9 F N2 O6 S2'
_chemical_formula_sum            'C12 H9 F N2 O6 S2'
_chemical_formula_weight         360.33
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   11.9044(5)
_cell_length_b                   7.9513(3)
_cell_length_c                   15.0809(5)
_cell_angle_alpha                90
_cell_angle_beta                 94.216(4)
_cell_angle_gamma                90
_cell_volume                     1423.63(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4249
_cell_measurement_temperature    170.00(10)
_cell_measurement_theta_max      30.4350
_cell_measurement_theta_min      2.1980
_shelx_estimated_absorpt_T_max   0.932
_shelx_estimated_absorpt_T_min   0.850
_exptl_absorpt_coefficient_mu    0.420
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_correction_T_min  0.989
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.99a (Rigaku Oxford Diffraction, 2021)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.681
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             736
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-13 -3 13 0.0583
-12 -8 2 0.1332
-11 4 -13 0.1210
-11 0 17 0.0774
-6 10 -3 0.1805
-3 11 1 0.1950
-1 -10 -8 0.1821
6 9 10 0.2013
8 6 14 0.1783
11 0 -18 0.1112
11 -1 15 0.1317
12 2 -15 0.1009
13 6 -8 0.1513
8 -9 6 0.0953
11 -6 11 0.1106

_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.17
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0224
_diffrn_reflns_av_unetI/netI     0.0307
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            6944
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.364
_diffrn_reflns_theta_min         2.262
_diffrn_ambient_temperature      170.15
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.981
_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     27.00  53.00   0.50   11.00    --   20.00  54.00  90.00   52
  2  ω    -29.00  17.00   0.50   11.00    --   20.00  54.00 -90.00   92
  3  ω     50.00  76.00   0.50   11.00    --   20.00  54.00 -90.00   52
  4  ω    -41.00  10.00   0.50   11.00    --   20.00  54.00-120.00  102
  5  ω    -74.00 106.00   0.50   11.00    --   20.00  54.00 120.00  360
  6  ω    -60.00 -35.00   0.50   11.00    --   20.00  54.00  90.00   50
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini II'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2362
_reflns_number_total             2826
_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 1.171.41.99a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.99a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.99a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.318
_refine_diff_density_min         -0.426
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2826
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0403
_refine_ls_R_factor_gt           0.0316
_refine_ls_restrained_S_all      1.035
_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)+(0.0489P)²+0.4463P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0857
_refine_ls_wR_factor_ref         0.0898
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00E(H00E), C00F(H00F), C00H(H00H), C00I(H00I), C00J(H00J), C00K(H00K),
 C00L(H00L), C00M(H00M), C00N(H00N)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S001 S 0.20793(4) 0.37946(5) 0.56346(3) 0.02098(13) Uani 1 1 d . . . . .
S002 S 0.41644(4) 0.38657(5) 0.69437(3) 0.02081(13) Uani 1 1 d . . . . .
F003 F 0.39908(9) 0.48689(14) 0.53383(7) 0.0300(3) Uani 1 1 d . . . . .
O004 O 0.50962(12) 0.49805(16) 0.70101(9) 0.0322(3) Uani 1 1 d . . . . .
O005 O 0.34098(12) 0.37409(17) 0.76260(8) 0.0305(3) Uani 1 1 d . . . . .
O006 O 0.14247(12) 0.36477(19) 0.63727(9) 0.0365(4) Uani 1 1 d . . . . .
O007 O 0.23350(13) 0.23760(16) 0.51150(9) 0.0360(4) Uani 1 1 d . . . . .
O008 O 0.08364(14) 0.2788(2) 0.35835(10) 0.0456(4) Uani 1 1 d . . . . .
N009 N 0.33086(12) 0.47434(18) 0.60704(9) 0.0196(3) Uani 1 1 d . . . . .
N00A N 0.16026(16) 0.3790(2) 0.35412(11) 0.0340(4) Uani 1 1 d . . . . .
C00B C 0.16132(14) 0.5474(2) 0.49435(11) 0.0192(4) Uani 1 1 d . . . . .
C00C C 0.45844(15) 0.1890(2) 0.65964(11) 0.0188(4) Uani 1 1 d . . . . .
O00D O 0.24203(17) 0.3609(3) 0.31128(13) 0.0654(6) Uani 1 1 d . . . . .
C00E C 0.56183(16) 0.1721(2) 0.62404(12) 0.0249(4) Uani 1 1 d . . . . .
H00E H 0.608769 0.267027 0.616990 0.030 Uiso 1 1 calc R U . . .
C00F C 0.38841(16) 0.0525(2) 0.67118(12) 0.0244(4) Uani 1 1 d . . . . .
H00F H 0.317816 0.066914 0.695755 0.029 Uiso 1 1 calc R U . . .
C00G C 0.15114(15) 0.5390(2) 0.40193(12) 0.0233(4) Uani 1 1 d . . . . .
C00H C 0.14394(16) 0.7004(2) 0.53566(13) 0.0273(4) Uani 1 1 d . . . . .
H00H H 0.149298 0.707582 0.598709 0.033 Uiso 1 1 calc R U . . .
C00I C 0.52633(18) -0.1240(2) 0.61022(13) 0.0300(5) Uani 1 1 d . . . . .
H00I H 0.549933 -0.232623 0.593076 0.036 Uiso 1 1 calc R U . . .
C00J C 0.42359(18) -0.1046(2) 0.64615(13) 0.0293(5) Uani 1 1 d . . . . .
H00J H 0.377059 -0.199894 0.653637 0.035 Uiso 1 1 calc R U . . .
C00K C 0.59497(17) 0.0133(3) 0.59903(13) 0.0304(4) Uani 1 1 d . . . . .
H00K H 0.665269 -0.001335 0.574036 0.036 Uiso 1 1 calc R U . . .
C00L C 0.11892(18) 0.8419(3) 0.48514(16) 0.0375(5) Uani 1 1 d . . . . .
H00L H 0.106947 0.946462 0.513465 0.045 Uiso 1 1 calc R U . . .
C00M C 0.12704(17) 0.6808(3) 0.35160(13) 0.0355(5) Uani 1 1 d . . . . .
H00M H 0.121356 0.674349 0.288530 0.043 Uiso 1 1 calc R U . . .
C00N C 0.11123(18) 0.8320(3) 0.39353(16) 0.0423(6) Uani 1 1 d . . . . .
H00N H 0.094902 0.930257 0.359099 0.051 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
S001 O006 1.4098(14) . ?
S001 O007 1.4192(14) . ?
S001 N009 1.7324(15) . ?
S001 C00B 1.7585(17) . ?
S002 O004 1.4177(14) . ?
S002 O005 1.4182(14) . ?
S002 N009 1.7500(14) . ?
S002 C00C 1.7407(17) . ?
F003 N009 1.4213(17) . ?
O008 N00A 1.216(2) . ?
N00A O00D 1.216(2) . ?
N00A C00G 1.470(2) . ?
C00B C00G 1.392(2) . ?
C00B C00H 1.389(2) . ?
C00C C00E 1.385(3) . ?
C00C C00F 1.388(2) . ?
C00E H00E 0.9500 . ?
C00E C00K 1.383(3) . ?
C00F H00F 0.9500 . ?
C00F C00J 1.379(3) . ?
C00G C00M 1.377(3) . ?
C00H H00H 0.9500 . ?
C00H C00L 1.379(3) . ?
C00I H00I 0.9500 . ?
C00I C00J 1.382(3) . ?
C00I C00K 1.382(3) . ?
C00J H00J 0.9500 . ?
C00K H00K 0.9500 . ?
C00L H00L 0.9500 . ?
C00L C00N 1.380(3) . ?
C00M H00M 0.9500 . ?
C00M C00N 1.378(3) . ?
C00N H00N 0.9500 . ?

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
O006 S001 O007 121.57(9) . . ?
O006 S001 N009 103.71(8) . . ?
O006 S001 C00B 111.24(9) . . ?
O007 S001 N009 110.24(8) . . ?
O007 S001 C00B 110.34(8) . . ?
N009 S001 C00B 96.61(7) . . ?
O004 S002 O005 121.77(9) . . ?
O004 S002 N009 102.30(7) . . ?
O004 S002 C00C 110.18(8) . . ?
O005 S002 N009 102.07(8) . . ?
O005 S002 C00C 111.49(8) . . ?
C00C S002 N009 107.31(8) . . ?
S001 N009 S002 122.73(8) . . ?
F003 N009 S001 104.53(9) . . ?
F003 N009 S002 106.16(9) . . ?
O008 N00A C00G 117.29(17) . . ?
O00D N00A O008 125.66(19) . . ?
O00D N00A C00G 117.00(19) . . ?
C00G C00B S001 123.88(14) . . ?
C00H C00B S001 116.76(13) . . ?
C00H C00B C00G 119.09(17) . . ?
C00E C00C S002 119.18(14) . . ?
C00E C00C C00F 122.12(17) . . ?
C00F C00C S002 118.67(14) . . ?
C00C C00E H00E 120.9 . . ?
C00K C00E C00C 118.29(18) . . ?
C00K C00E H00E 120.9 . . ?
C00C C00F H00F 120.8 . . ?
C00J C00F C00C 118.50(17) . . ?
C00J C00F H00F 120.8 . . ?
C00B C00G N00A 121.90(16) . . ?
C00M C00G N00A 117.25(17) . . ?
C00M C00G C00B 120.79(18) . . ?
C00B C00H H00H 120.0 . . ?
C00L C00H C00B 120.00(18) . . ?
C00L C00H H00H 120.0 . . ?
C00J C00I H00I 119.7 . . ?
C00K C00I H00I 119.7 . . ?
C00K C00I C00J 120.54(17) . . ?
C00F C00J C00I 120.23(18) . . ?
C00F C00J H00J 119.9 . . ?
C00I C00J H00J 119.9 . . ?
C00E C00K H00K 119.8 . . ?
C00I C00K C00E 120.32(19) . . ?
C00I C00K H00K 119.8 . . ?
C00H C00L H00L 119.9 . . ?
C00H C00L C00N 120.1(2) . . ?
C00N C00L H00L 119.9 . . ?
C00G C00M H00M 120.3 . . ?
C00G C00M C00N 119.43(18) . . ?
C00N C00M H00M 120.3 . . ?
C00L C00N H00N 119.7 . . ?
C00M C00N C00L 120.52(19) . . ?
C00M C00N H00N 119.7 . . ?

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
S001 C00B C00G N00A 10.7(3) . . . . ?
S001 C00B C00G C00M -172.22(15) . . . . ?
S001 C00B C00H C00L 173.19(15) . . . . ?
S002 C00C C00E C00K 178.31(14) . . . . ?
S002 C00C C00F C00J -177.99(14) . . . . ?
O004 S002 N009 S001 174.87(10) . . . . ?
O004 S002 N009 F003 55.09(11) . . . . ?
O004 S002 C00C C00E -14.65(17) . . . . ?
O004 S002 C00C C00F 163.37(13) . . . . ?
O005 S002 N009 S001 -58.42(11) . . . . ?
O005 S002 N009 F003 -178.21(10) . . . . ?
O005 S002 C00C C00E -153.03(14) . . . . ?
O005 S002 C00C C00F 24.98(16) . . . . ?
O006 S001 N009 S002 58.21(12) . . . . ?
O006 S001 N009 F003 178.77(10) . . . . ?
O006 S001 C00B C00G -137.71(16) . . . . ?
O006 S001 C00B C00H 48.29(17) . . . . ?
O007 S001 N009 S002 -73.42(12) . . . . ?
O007 S001 N009 F003 47.13(11) . . . . ?
O007 S001 C00B C00G 0.29(18) . . . . ?
O007 S001 C00B C00H -173.71(15) . . . . ?
O008 N00A C00G C00B 70.4(2) . . . . ?
O008 N00A C00G C00M -106.8(2) . . . . ?
N009 S001 C00B C00G 114.77(16) . . . . ?
N009 S001 C00B C00H -59.23(16) . . . . ?
N009 S002 C00C C00E 95.98(15) . . . . ?
N009 S002 C00C C00F -86.01(15) . . . . ?
N00A C00G C00M C00N 176.28(19) . . . . ?
C00B S001 N009 S002 172.02(10) . . . . ?
C00B S001 N009 F003 -67.43(10) . . . . ?
C00B C00G C00M C00N -1.0(3) . . . . ?
C00B C00H C00L C00N -0.1(3) . . . . ?
C00C S002 N009 S001 58.91(12) . . . . ?
C00C S002 N009 F003 -60.87(11) . . . . ?
C00C C00E C00K C00I -0.5(3) . . . . ?
C00C C00F C00J C00I -0.2(3) . . . . ?
O00D N00A C00G C00B -112.0(2) . . . . ?
O00D N00A C00G C00M 70.8(2) . . . . ?
C00E C00C C00F C00J 0.0(3) . . . . ?
C00F C00C C00E C00K 0.4(3) . . . . ?
C00G C00B C00H C00L -1.1(3) . . . . ?
C00G C00M C00N C00L -0.3(3) . . . . ?
C00H C00B C00G N00A -175.46(17) . . . . ?
C00H C00B C00G C00M 1.6(3) . . . . ?
C00H C00L C00N C00M 0.8(3) . . . . ?
C00J C00I C00K C00E 0.3(3) . . . . ?
C00K C00I C00J C00F 0.1(3) . . . . ?

_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
;
####################################################################### 
# 
# 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_4ea_auto
_audit_block_doi                 10.5517/ccdc.csd.cc2f02sb
_database_code_depnum_ccdc_archive 'CCDC 2234411'
loop_
_audit_author_name
_audit_author_address
'Kohsuke Aikawa'
;The University of Tokyo
Japan
;
_audit_update_record             
;
2023-05-02 deposited with the CCDC.	2023-06-22 downloaded from the CCDC.
;
_audit_creation_date             2022-08-11
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H16 F2 N2 O6 S2'
_chemical_formula_sum            'C20 H16 F2 N2 O6 S2'
_chemical_formula_weight         482.47
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   16.0194(10)
_cell_length_b                   11.6755(8)
_cell_length_c                   21.8846(17)
_cell_angle_alpha                90
_cell_angle_beta                 92.959(7)
_cell_angle_gamma                90
_cell_volume                     4087.7(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    5522
_cell_measurement_temperature    175(7)
_cell_measurement_theta_max      30.0920
_cell_measurement_theta_min      2.1820
_shelx_estimated_absorpt_T_max   0.959
_shelx_estimated_absorpt_T_min   0.893
_exptl_absorpt_coefficient_mu    0.321
_exptl_absorpt_correction_T_max  0.925
_exptl_absorpt_correction_T_min  0.844
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.99a (Rigaku Oxford Diffraction, 2021)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.568
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1984
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
14 12 -10 0.0044
13 12 -12 0.0179
13 13 6 0.0598
3 5 29 0.1352
-14 -13 5 0.1126
10 7 -25 0.1276
16 -6 18 0.0502
8 -9 -24 0.1522
-18 8 -9 0.1475
-18 10 0 0.1440
-13 11 17 0.1543
-10 -7 25 0.1329

_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.13
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0231
_diffrn_reflns_av_unetI/netI     0.0298
_diffrn_reflns_Laue_measured_fraction_full 0.953
_diffrn_reflns_Laue_measured_fraction_max 0.948
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            10657
_diffrn_reflns_point_group_measured_fraction_full 0.953
_diffrn_reflns_point_group_measured_fraction_max 0.948
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.369
_diffrn_reflns_theta_min         2.159
_diffrn_ambient_temperature      175.15
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.953
_diffrn_measured_fraction_theta_max 0.948
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -29.00  59.00   0.50   42.00    --   20.00  54.00  60.00  176
  2  ω     73.00 110.00   0.50   42.00    --   20.00  54.00  60.00   74
  3  ω    -69.00 -34.00   0.50   42.00    --   20.00  54.00-150.00   70
  4  ω     11.00  36.00   0.50   42.00    --   20.00  54.00-150.00   50
  5  ω     72.00 109.00   0.50   42.00    --   20.00  54.00-150.00   74
  6  ω    -59.00 -33.00   0.50   42.00    --   20.00  54.00 -60.00   52
  7  ω     -3.00  22.00   0.50   42.00    --   20.00  54.00 -60.00   50
  8  ω    -71.00  29.00   0.50   42.00    --   20.00  54.00 120.00  200
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini II'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3331
_reflns_number_total             3971
_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 1.171.41.99a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.99a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.99a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         1.031
_refine_diff_density_min         -0.331
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         3971
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0465
_refine_ls_R_factor_gt           0.0365
_refine_ls_restrained_S_all      1.033
_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)+(0.0509P)²+3.9683P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0935
_refine_ls_wR_factor_ref         0.0978
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C00G(H00G)
2.b Secondary CH2 refined with riding coordinates:
 C00U(H00A,H00B)
2.c Aromatic/amide H refined with riding coordinates:
 C00H(H00H), C00I(H00I), C00K(H00K), C00L(H00L), C00M(H00M), C00O(H00O),
 C00P(H00P), C00Q(H00Q), C00R(H00R), C00S(H00S), C00T(H00T), C00V(H00V),
 C00W(H00W)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S001 S 0.18070(3) 0.59787(4) 0.36455(2) 0.02112(13) Uani 1 1 d . . . . .
S002 S 0.32137(3) 0.44175(4) 0.39367(2) 0.02143(13) Uani 1 1 d . . . . .
F003 F 0.40051(9) 0.70016(12) 0.24469(6) 0.0433(4) Uani 1 1 d . . . . .
O004 O 0.17384(9) 0.71450(12) 0.38292(6) 0.0262(3) Uani 1 1 d . . . . .
O005 O 0.26764(10) 0.35021(12) 0.37472(7) 0.0300(3) Uani 1 1 d . . . . .
F006 F 0.55495(9) 0.86676(14) 0.51204(7) 0.0506(4) Uani 1 1 d . . . . .
O007 O 0.14253(9) 0.50996(12) 0.39837(6) 0.0287(3) Uani 1 1 d . . . . .
O008 O 0.40626(9) 0.44264(12) 0.37646(7) 0.0283(3) Uani 1 1 d . . . . .
O009 O 0.07511(10) 0.85575(13) 0.29000(8) 0.0353(4) Uani 1 1 d . . . . .
O00A O 0.20599(10) 0.84194(13) 0.26998(7) 0.0349(4) Uani 1 1 d . . . . .
N00B N 0.13537(11) 0.80265(14) 0.27305(8) 0.0262(4) Uani 1 1 d . . . . .
N00C N 0.28215(10) 0.56528(13) 0.36302(7) 0.0207(3) Uani 1 1 d . . . . .
C00D C 0.39844(12) 0.70850(16) 0.38338(8) 0.0199(4) Uani 1 1 d . . . . .
C00E C 0.31941(12) 0.45880(16) 0.47333(9) 0.0223(4) Uani 1 1 d . . . . .
C00F C 0.12119(12) 0.68349(17) 0.25132(9) 0.0222(4) Uani 1 1 d . . . . .
C00G C 0.33759(12) 0.65398(16) 0.33631(9) 0.0209(4) Uani 1 1 d . . . . .
H00G H 0.299167 0.717249 0.322217 0.025 Uiso 1 1 calc R U . . .
C00H C 0.38294(13) 0.52219(17) 0.50368(10) 0.0266(4) Uani 1 1 d . . . . .
H00H H 0.426959 0.554582 0.481880 0.032 Uiso 1 1 calc R U . . .
C00I C 0.48445(13) 0.69432(17) 0.38250(10) 0.0260(4) Uani 1 1 d . . . . .
H00I H 0.507127 0.647161 0.352103 0.031 Uiso 1 1 calc R U . . .
C00J C 0.14304(11) 0.58874(17) 0.28728(9) 0.0210(4) Uani 1 1 d . . . . .
C00K C 0.36649(13) 0.77993(17) 0.42760(9) 0.0265(4) Uani 1 1 d . . . . .
H00K H 0.307856 0.791883 0.427970 0.032 Uiso 1 1 calc R U . . .
C00L C 0.08527(13) 0.67242(19) 0.19315(9) 0.0277(5) Uani 1 1 d . . . . .
H00L H 0.070878 0.738151 0.169283 0.033 Uiso 1 1 calc R U . . .
C00M C 0.12791(13) 0.47968(18) 0.26327(10) 0.0283(5) Uani 1 1 d . . . . .
H00M H 0.142277 0.413701 0.286949 0.034 Uiso 1 1 calc R U . . .
C00N C 0.50314(14) 0.81549(19) 0.46888(10) 0.0317(5) Uani 1 1 d . . . . .
C00O C 0.25549(13) 0.40877(18) 0.50393(10) 0.0275(4) Uani 1 1 d . . . . .
H00O H 0.213278 0.365303 0.482476 0.033 Uiso 1 1 calc R U . . .
C00P C 0.41879(14) 0.83360(19) 0.47088(10) 0.0325(5) Uani 1 1 d . . . . .
H00P H 0.396884 0.881714 0.501183 0.039 Uiso 1 1 calc R U . . .
C00Q C 0.07048(13) 0.5630(2) 0.17007(10) 0.0314(5) Uani 1 1 d . . . . .
H00Q H 0.045456 0.553556 0.130082 0.038 Uiso 1 1 calc R U . . .
C00R C 0.53771(13) 0.74832(19) 0.42556(11) 0.0334(5) Uani 1 1 d . . . . .
H00R H 0.596562 0.738885 0.424964 0.040 Uiso 1 1 calc R U . . .
C00S C 0.31598(15) 0.48809(19) 0.59727(10) 0.0352(5) Uani 1 1 d . . . . .
H00S H 0.314079 0.499175 0.640182 0.042 Uiso 1 1 calc R U . . .
C00T C 0.09199(14) 0.46804(19) 0.20496(10) 0.0328(5) Uani 1 1 d . . . . .
H00T H 0.081916 0.393661 0.188596 0.039 Uiso 1 1 calc R U . . .
C00U C 0.37387(14) 0.60751(18) 0.27844(9) 0.0301(5) Uani 1 1 d . . . . .
H00A H 0.421478 0.555939 0.289068 0.036 Uiso 1 1 calc R U . . .
H00B H 0.330855 0.563544 0.254287 0.036 Uiso 1 1 calc R U . . .
C00V C 0.38002(15) 0.53650(18) 0.56622(10) 0.0328(5) Uani 1 1 d . . . . .
H00V H 0.422166 0.579731 0.587891 0.039 Uiso 1 1 calc R U . . .
C00W C 0.25451(15) 0.4236(2) 0.56670(10) 0.0343(5) Uani 1 1 d . . . . .
H00W H 0.211518 0.389418 0.588833 0.041 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
S001 O004 1.4257(14) . ?
S001 O007 1.4219(15) . ?
S001 N00C 1.6710(16) . ?
S001 C00J 1.769(2) . ?
S002 O005 1.4207(15) . ?
S002 O008 1.4297(15) . ?
S002 N00C 1.6975(16) . ?
S002 C00E 1.757(2) . ?
F003 C00U 1.389(2) . ?
F006 C00N 1.363(2) . ?
O009 N00B 1.221(2) . ?
O00A N00B 1.226(2) . ?
N00B C00F 1.484(3) . ?
N00C C00G 1.502(2) . ?
C00D C00G 1.521(3) . ?
C00D C00I 1.389(3) . ?
C00D C00K 1.395(3) . ?
C00E C00H 1.398(3) . ?
C00E C00O 1.382(3) . ?
C00F C00J 1.392(3) . ?
C00F C00L 1.376(3) . ?
C00G H00G 1.0000 . ?
C00G C00U 1.520(3) . ?
C00H H00H 0.9500 . ?
C00H C00V 1.382(3) . ?
C00I H00I 0.9500 . ?
C00I C00R 1.389(3) . ?
C00J C00M 1.394(3) . ?
C00K H00K 0.9500 . ?
C00K C00P 1.382(3) . ?
C00L H00L 0.9500 . ?
C00L C00Q 1.389(3) . ?
C00M H00M 0.9500 . ?
C00M C00T 1.379(3) . ?
C00N C00P 1.371(3) . ?
C00N C00R 1.369(3) . ?
C00O H00O 0.9500 . ?
C00O C00W 1.386(3) . ?
C00P H00P 0.9500 . ?
C00Q H00Q 0.9500 . ?
C00Q C00T 1.380(3) . ?
C00R H00R 0.9500 . ?
C00S H00S 0.9500 . ?
C00S C00V 1.380(3) . ?
C00S C00W 1.384(3) . ?
C00T H00T 0.9500 . ?
C00U H00A 0.9900 . ?
C00U H00B 0.9900 . ?
C00V H00V 0.9500 . ?
C00W H00W 0.9500 . ?

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
O004 S001 N00C 108.20(8) . . ?
O004 S001 C00J 107.43(9) . . ?
O007 S001 O004 120.08(9) . . ?
O007 S001 N00C 106.92(8) . . ?
O007 S001 C00J 108.63(9) . . ?
N00C S001 C00J 104.55(9) . . ?
O005 S002 O008 119.92(9) . . ?
O005 S002 N00C 108.52(9) . . ?
O005 S002 C00E 109.48(9) . . ?
O008 S002 N00C 103.15(8) . . ?
O008 S002 C00E 109.06(9) . . ?
N00C S002 C00E 105.70(9) . . ?
O009 N00B O00A 124.96(18) . . ?
O009 N00B C00F 117.58(17) . . ?
O00A N00B C00F 117.37(17) . . ?
S001 N00C S002 121.74(9) . . ?
C00G N00C S001 116.49(12) . . ?
C00G N00C S002 121.69(13) . . ?
C00I C00D C00G 122.84(18) . . ?
C00I C00D C00K 118.73(19) . . ?
C00K C00D C00G 118.36(17) . . ?
C00H C00E S002 118.79(15) . . ?
C00O C00E S002 119.00(16) . . ?
C00O C00E C00H 122.21(19) . . ?
C00J C00F N00B 122.28(17) . . ?
C00L C00F N00B 115.75(18) . . ?
C00L C00F C00J 121.97(19) . . ?
N00C C00G C00D 113.33(15) . . ?
N00C C00G H00G 105.2 . . ?
N00C C00G C00U 109.71(15) . . ?
C00D C00G H00G 105.2 . . ?
C00U C00G C00D 117.02(17) . . ?
C00U C00G H00G 105.2 . . ?
C00E C00H H00H 120.9 . . ?
C00V C00H C00E 118.3(2) . . ?
C00V C00H H00H 120.9 . . ?
C00D C00I H00I 119.6 . . ?
C00D C00I C00R 120.75(19) . . ?
C00R C00I H00I 119.6 . . ?
C00F C00J S001 123.78(15) . . ?
C00F C00J C00M 118.63(19) . . ?
C00M C00J S001 117.35(16) . . ?
C00D C00K H00K 119.5 . . ?
C00P C00K C00D 121.03(19) . . ?
C00P C00K H00K 119.5 . . ?
C00F C00L H00L 120.7 . . ?
C00F C00L C00Q 118.6(2) . . ?
C00Q C00L H00L 120.7 . . ?
C00J C00M H00M 120.2 . . ?
C00T C00M C00J 119.7(2) . . ?
C00T C00M H00M 120.2 . . ?
F006 C00N C00P 118.4(2) . . ?
F006 C00N C00R 118.5(2) . . ?
C00R C00N C00P 123.0(2) . . ?
C00E C00O H00O 120.8 . . ?
C00E C00O C00W 118.3(2) . . ?
C00W C00O H00O 120.8 . . ?
C00K C00P H00P 120.9 . . ?
C00N C00P C00K 118.2(2) . . ?
C00N C00P H00P 120.9 . . ?
C00L C00Q H00Q 119.8 . . ?
C00T C00Q C00L 120.3(2) . . ?
C00T C00Q H00Q 119.8 . . ?
C00I C00R H00R 120.9 . . ?
C00N C00R C00I 118.3(2) . . ?
C00N C00R H00R 120.9 . . ?
C00V C00S H00S 119.6 . . ?
C00V C00S C00W 120.9(2) . . ?
C00W C00S H00S 119.6 . . ?
C00M C00T C00Q 120.9(2) . . ?
C00M C00T H00T 119.6 . . ?
C00Q C00T H00T 119.6 . . ?
F003 C00U C00G 107.82(16) . . ?
F003 C00U H00A 110.1 . . ?
F003 C00U H00B 110.1 . . ?
C00G C00U H00A 110.1 . . ?
C00G C00U H00B 110.1 . . ?
H00A C00U H00B 108.5 . . ?
C00H C00V H00V 119.9 . . ?
C00S C00V C00H 120.1(2) . . ?
C00S C00V H00V 119.9 . . ?
C00O C00W H00W 119.9 . . ?
C00S C00W C00O 120.2(2) . . ?
C00S C00W H00W 119.9 . . ?

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
S001 N00C C00G C00D 111.74(16) . . . . ?
S001 N00C C00G C00U -115.40(16) . . . . ?
S001 C00J C00M C00T 174.61(16) . . . . ?
S002 N00C C00G C00D -64.9(2) . . . . ?
S002 N00C C00G C00U 67.9(2) . . . . ?
S002 C00E C00H C00V 179.02(15) . . . . ?
S002 C00E C00O C00W -179.60(16) . . . . ?
O004 S001 N00C S002 134.70(11) . . . . ?
O004 S001 N00C C00G -41.96(15) . . . . ?
O004 S001 C00J C00F 6.98(19) . . . . ?
O004 S001 C00J C00M -167.31(15) . . . . ?
O005 S002 N00C S001 45.51(14) . . . . ?
O005 S002 N00C C00G -138.00(14) . . . . ?
O005 S002 C00E C00H 163.33(15) . . . . ?
O005 S002 C00E C00O -16.36(19) . . . . ?
F006 C00N C00P C00K -179.0(2) . . . . ?
F006 C00N C00R C00I 178.63(19) . . . . ?
O007 S001 N00C S002 4.05(14) . . . . ?
O007 S001 N00C C00G -172.61(13) . . . . ?
O007 S001 C00J C00F 138.30(16) . . . . ?
O007 S001 C00J C00M -36.00(18) . . . . ?
O008 S002 N00C S001 173.71(11) . . . . ?
O008 S002 N00C C00G -9.80(16) . . . . ?
O008 S002 C00E C00H 30.33(18) . . . . ?
O008 S002 C00E C00O -149.35(15) . . . . ?
O009 N00B C00F C00J -102.7(2) . . . . ?
O009 N00B C00F C00L 77.6(2) . . . . ?
O00A N00B C00F C00J 80.6(2) . . . . ?
O00A N00B C00F C00L -99.2(2) . . . . ?
N00B C00F C00J S001 6.1(3) . . . . ?
N00B C00F C00J C00M -179.71(18) . . . . ?
N00B C00F C00L C00Q 179.88(18) . . . . ?
N00C S001 C00J C00F -107.83(17) . . . . ?
N00C S001 C00J C00M 77.87(16) . . . . ?
N00C S002 C00E C00H -79.97(17) . . . . ?
N00C S002 C00E C00O 100.34(16) . . . . ?
N00C C00G C00U F003 160.42(16) . . . . ?
C00D C00G C00U F003 -68.7(2) . . . . ?
C00D C00I C00R C00N 0.2(3) . . . . ?
C00D C00K C00P C00N 0.5(3) . . . . ?
C00E S002 N00C S001 -71.83(13) . . . . ?
C00E S002 N00C C00G 104.65(15) . . . . ?
C00E C00H C00V C00S 0.5(3) . . . . ?
C00E C00O C00W C00S 0.6(3) . . . . ?
C00F C00J C00M C00T 0.0(3) . . . . ?
C00F C00L C00Q C00T -0.3(3) . . . . ?
C00G C00D C00I C00R 178.30(18) . . . . ?
C00G C00D C00K C00P -178.80(18) . . . . ?
C00H C00E C00O C00W 0.7(3) . . . . ?
C00I C00D C00G N00C 114.1(2) . . . . ?
C00I C00D C00G C00U -15.1(3) . . . . ?
C00I C00D C00K C00P -1.7(3) . . . . ?
C00J S001 N00C S002 -111.03(12) . . . . ?
C00J S001 N00C C00G 72.32(15) . . . . ?
C00J C00F C00L C00Q 0.1(3) . . . . ?
C00J C00M C00T C00Q -0.2(3) . . . . ?
C00K C00D C00G N00C -68.9(2) . . . . ?
C00K C00D C00G C00U 161.92(18) . . . . ?
C00K C00D C00I C00R 1.3(3) . . . . ?
C00L C00F C00J S001 -174.17(15) . . . . ?
C00L C00F C00J C00M 0.1(3) . . . . ?
C00L C00Q C00T C00M 0.4(3) . . . . ?
C00O C00E C00H C00V -1.3(3) . . . . ?
C00P C00N C00R C00I -1.4(4) . . . . ?
C00R C00N C00P C00K 1.0(4) . . . . ?
C00V C00S C00W C00O -1.4(3) . . . . ?
C00W C00S C00V C00H 0.8(3) . . . . ?

_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
;
####################################################################### 
# 
# 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_20-01-122-2_auto
_audit_block_doi                 10.5517/ccdc.csd.cc2f02q8
_database_code_depnum_ccdc_archive 'CCDC 2234409'
loop_
_audit_author_name
_audit_author_address
'Kohsuke Aikawa'
;The University of Tokyo
Japan
;
_audit_update_record             
;
2023-05-02 deposited with the CCDC.	2023-06-22 downloaded from the CCDC.
;
_audit_creation_date             2021-03-18
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H14 F2 N2 O6 S2'
_chemical_formula_sum            'C15 H14 F2 N2 O6 S2'
_chemical_formula_weight         420.40
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   14.6054(6)
_cell_length_b                   8.9495(3)
_cell_length_c                   14.5067(6)
_cell_angle_alpha                90
_cell_angle_beta                 117.306(5)
_cell_angle_gamma                90
_cell_volume                     1684.89(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    16291
_cell_measurement_temperature    169.99(10)
_cell_measurement_theta_max      30.3490
_cell_measurement_theta_min      2.7480
_shelx_estimated_absorpt_T_max   0.916
_shelx_estimated_absorpt_T_min   0.850
_exptl_absorpt_coefficient_mu    0.376
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97793
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.99a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.657
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.446
_exptl_crystal_size_mid          0.318
_exptl_crystal_size_min          0.237
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0280
_diffrn_reflns_av_unetI/netI     0.0174
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            28297
_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         26.371
_diffrn_reflns_theta_min         2.765
_diffrn_ambient_temperature      170.15
_diffrn_detector_area_resol_mean 10.0000
_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    -15.00  28.00   0.50    3.61    --   20.00  54.00 -90.00   86
  2  ω     34.00  80.00   0.50    3.61    --   20.00  54.00 -90.00   92
  3  ω    -74.00  28.00   0.50    3.61    --   20.00  54.00  30.00  204
  4  ω     32.00  99.00   0.50    3.61    --   20.00  54.00  30.00  134
  5  ω     11.00  43.00   0.50    3.61    --   20.00  54.00 150.00   64
  6  ω     65.00  90.00   0.50    3.61    --   20.00  54.00 150.00   50
  7  ω    -74.00 108.00   0.50    3.61    --   20.00  54.00-150.00  364
  8  ω    -73.00 -48.00   0.50    3.61    --   20.00  54.00  90.00   50
  9  ω     75.00 100.00   0.50    3.61    --   20.00  54.00  90.00   50
 10  ω    -73.00  46.00   0.50    3.61    --   20.00  54.00 -60.00  238
 11  ω     53.00  78.00   0.50    3.61    --   20.00  54.00 -60.00   50
 12  ω    -67.00  69.00   0.50    3.61    --   20.00  54.00 120.00  272
 13  ω    -70.00 -43.00   0.50    3.61    --   20.00  54.00   0.00   54
 14  ω     79.00 104.00   0.50    3.61    --   20.00  54.00   0.00   50
 15  ω    -67.00 -40.00   0.50    3.61    --   20.00  54.00 -30.00   54
 16  ω    -12.00  13.00   0.50    3.61    --   20.00  54.00 -30.00   50
 17  ω     69.00  94.00   0.50    3.61    --   20.00  54.00 -30.00   50
 18  ω    -69.00  34.00   0.50    3.61    --   20.00  54.00-180.00  206
 19  ω     84.00 109.00   0.50    3.61    --   20.00  54.00-180.00   50
 20  ω    -69.00 -44.00   0.50    3.61    --   20.00  54.00-120.00   50
 21  ω     46.00  71.00   0.50    3.61    --   20.00  54.00-120.00   50
 22  ω    -20.00   5.00   0.50    3.61    --   20.00  54.00  60.00   50
 23  ω     16.00  41.00   0.50    3.61    --   20.00  54.00  60.00   50
 24  ω    -72.00 -47.00   0.50    3.61    --   20.00  54.00 -90.00   50
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini II'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3042
_reflns_number_total             3440
_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 1.171.41.99a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.99a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.99a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.374
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3440
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0336
_refine_ls_R_factor_gt           0.0291
_refine_ls_restrained_S_all      1.061
_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)+(0.0408P)²+0.7290P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0765
_refine_ls_wR_factor_ref         0.0787
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C00F(H00F)
2.b Aromatic/amide H refined with riding coordinates:
 C00E(H00E), C00I(H00I), C00J(H00J), C00K(H00K), C00M(H00M), C00O(H00O),
 C00Q(H00Q), C00R(H00R)
2.c Idealised Me refined as rotating group:
 C00P(H00C,H00D,H00G)
;
_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
S001 S 0.28647(3) 0.35283(4) 0.47855(3) 0.02090(10) Uani 1 1 d . . . . .
S002 S 0.25356(3) 0.60141(4) 0.33986(3) 0.02440(11) Uani 1 1 d . . . . .
F003 F 0.61109(8) 0.98325(12) 0.69057(9) 0.0397(3) Uani 1 1 d . . . . .
O004 O 0.30368(9) 0.33323(12) 0.58270(8) 0.0286(3) Uani 1 1 d . . . . .
O005 O 0.36787(8) 0.32106(12) 0.45300(9) 0.0294(3) Uani 1 1 d . . . . .
F006 F 0.13859(9) 0.76038(15) 0.57558(9) 0.0508(3) Uani 1 1 d . . . . .
O007 O 0.21702(9) 0.48423(13) 0.26536(8) 0.0308(3) Uani 1 1 d . . . . .
O008 O 0.19900(10) 0.73872(13) 0.32135(9) 0.0335(3) Uani 1 1 d . . . . .
O009 O 0.08323(10) 0.18161(14) 0.57123(9) 0.0371(3) Uani 1 1 d . . . . .
O00A O 0.09103(10) 0.40032(13) 0.51194(10) 0.0353(3) Uani 1 1 d . . . . .
N00B N 0.25262(9) 0.53196(14) 0.44770(9) 0.0207(3) Uani 1 1 d . . . . .
N00C N 0.09293(10) 0.26366(15) 0.50935(10) 0.0253(3) Uani 1 1 d . . . . .
C00D C 0.10336(11) 0.19488(17) 0.42301(11) 0.0209(3) Uani 1 1 d . . . . .
C00E C 0.18513(12) 0.16862(17) 0.31412(12) 0.0248(3) Uani 1 1 d . . . . .
H00E H 0.237884 0.194632 0.296008 0.030 Uiso 1 1 calc R U . . .
C00F C 0.25009(12) 0.63549(17) 0.52847(12) 0.0225(3) Uani 1 1 d . . . . .
H00F H 0.255204 0.570095 0.586536 0.027 Uiso 1 1 calc R U . . .
C00G C 0.18128(11) 0.23744(16) 0.39787(11) 0.0201(3) Uani 1 1 d . . . . .
C00H C 0.34445(12) 0.73598(17) 0.57424(12) 0.0235(3) Uani 1 1 d . . . . .
C00I C 0.43789(12) 0.67407(18) 0.64458(12) 0.0249(3) Uani 1 1 d . . . . .
H00I H 0.439728 0.572928 0.665242 0.030 Uiso 1 1 calc R U . . .
C00J C 0.03137(12) 0.08812(18) 0.36701(12) 0.0263(3) Uani 1 1 d . . . . .
H00J H -0.020655 0.060168 0.385694 0.032 Uiso 1 1 calc R U . . .
C00K C 0.03611(13) 0.02240(18) 0.28322(13) 0.0293(4) Uani 1 1 d . . . . .
H00K H -0.013514 -0.050725 0.243482 0.035 Uiso 1 1 calc R U . . .
C00L C 0.52296(13) 0.90190(19) 0.65369(13) 0.0291(4) Uani 1 1 d . . . . .
C00M C 0.52826(12) 0.75602(19) 0.68523(12) 0.0274(3) Uani 1 1 d . . . . .
H00M H 0.591794 0.712919 0.733303 0.033 Uiso 1 1 calc R U . . .
C00N C 0.14689(13) 0.7149(2) 0.48808(14) 0.0290(4) Uani 1 1 d . . . . .
C00O C 0.11233(13) 0.06198(18) 0.25665(12) 0.0287(4) Uani 1 1 d . . . . .
H00O H 0.114903 0.016028 0.198850 0.034 Uiso 1 1 calc R U . . .
C00P C 0.38263(14) 0.6394(2) 0.37105(15) 0.0350(4) Uani 1 1 d . . . . .
H00C H 0.423404 0.547672 0.395350 0.052 Uiso 1 1 calc R U . . .
H00D H 0.410042 0.715195 0.425866 0.052 Uiso 1 1 calc R U . . .
H00G H 0.386395 0.676562 0.309330 0.052 Uiso 1 1 calc R U . . .
C00Q C 0.43269(14) 0.9684(2) 0.58627(16) 0.0387(4) Uani 1 1 d . . . . .
H00Q H 0.431545 1.070044 0.566807 0.046 Uiso 1 1 calc R U . . .
C00R C 0.34259(14) 0.88464(19) 0.54671(15) 0.0356(4) Uani 1 1 d . . . . .
H00R H 0.279101 0.929689 0.500343 0.043 Uiso 1 1 calc R U . . .
H00A H 0.0874(12) 0.6483(17) 0.4427(12) 0.011(4) Uiso 1 1 d . . . . .
H00B H 0.1393(14) 0.800(2) 0.4479(15) 0.031(5) 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
S001 O004 1.4243(12) . ?
S001 O005 1.4269(12) . ?
S001 N00B 1.6767(13) . ?
S001 C00G 1.7739(15) . ?
S002 O007 1.4224(12) . ?
S002 O008 1.4215(12) . ?
S002 N00B 1.6892(13) . ?
S002 C00P 1.7583(18) . ?
F003 C00L 1.3569(18) . ?
F006 C00N 1.390(2) . ?
O009 N00C 1.2172(17) . ?
O00A N00C 1.2243(18) . ?
N00B C00F 1.5075(18) . ?
N00C C00D 1.4650(19) . ?
C00D C00G 1.398(2) . ?
C00D C00J 1.376(2) . ?
C00E H00E 0.9500 . ?
C00E C00G 1.386(2) . ?
C00E C00O 1.387(2) . ?
C00F H00F 1.0000 . ?
C00F C00H 1.520(2) . ?
C00F C00N 1.520(2) . ?
C00H C00I 1.390(2) . ?
C00H C00R 1.386(2) . ?
C00I H00I 0.9500 . ?
C00I C00M 1.383(2) . ?
C00J H00J 0.9500 . ?
C00J C00K 1.380(2) . ?
C00K H00K 0.9500 . ?
C00K C00O 1.381(2) . ?
C00L C00M 1.374(2) . ?
C00L C00Q 1.366(3) . ?
C00M H00M 0.9500 . ?
C00N H00A 1.009(16) . ?
C00N H00B 0.93(2) . ?
C00O H00O 0.9500 . ?
C00P H00C 0.9800 . ?
C00P H00D 0.9800 . ?
C00P H00G 0.9800 . ?
C00Q H00Q 0.9500 . ?
C00Q C00R 1.389(3) . ?
C00R H00R 0.9500 . ?

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
O004 S001 O005 119.24(7) . . ?
O004 S001 N00B 106.73(7) . . ?
O004 S001 C00G 107.83(7) . . ?
O005 S001 N00B 107.46(7) . . ?
O005 S001 C00G 106.57(7) . . ?
N00B S001 C00G 108.69(7) . . ?
O007 S002 N00B 105.83(7) . . ?
O007 S002 C00P 108.81(8) . . ?
O008 S002 O007 120.76(7) . . ?
O008 S002 N00B 104.54(7) . . ?
O008 S002 C00P 108.86(8) . . ?
N00B S002 C00P 107.22(8) . . ?
S001 N00B S002 118.19(7) . . ?
C00F N00B S001 119.31(10) . . ?
C00F N00B S002 120.47(10) . . ?
O009 N00C O00A 124.62(14) . . ?
O009 N00C C00D 118.03(13) . . ?
O00A N00C C00D 117.30(13) . . ?
C00G C00D N00C 121.67(13) . . ?
C00J C00D N00C 116.45(13) . . ?
C00J C00D C00G 121.87(14) . . ?
C00G C00E H00E 119.9 . . ?
C00G C00E C00O 120.30(15) . . ?
C00O C00E H00E 119.9 . . ?
N00B C00F H00F 106.0 . . ?
N00B C00F C00H 111.26(12) . . ?
N00B C00F C00N 111.19(12) . . ?
C00H C00F H00F 106.0 . . ?
C00H C00F C00N 115.59(13) . . ?
C00N C00F H00F 106.0 . . ?
C00D C00G S001 123.29(12) . . ?
C00E C00G S001 117.76(12) . . ?
C00E C00G C00D 118.22(14) . . ?
C00I C00H C00F 118.22(14) . . ?
C00R C00H C00F 123.25(14) . . ?
C00R C00H C00I 118.49(15) . . ?
C00H C00I H00I 119.2 . . ?
C00M C00I C00H 121.66(15) . . ?
C00M C00I H00I 119.2 . . ?
C00D C00J H00J 120.6 . . ?
C00D C00J C00K 118.83(15) . . ?
C00K C00J H00J 120.6 . . ?
C00J C00K H00K 119.7 . . ?
C00J C00K C00O 120.59(15) . . ?
C00O C00K H00K 119.7 . . ?
F003 C00L C00M 118.70(15) . . ?
F003 C00L C00Q 118.54(16) . . ?
C00Q C00L C00M 122.76(16) . . ?
C00I C00M H00M 121.1 . . ?
C00L C00M C00I 117.70(15) . . ?
C00L C00M H00M 121.1 . . ?
F006 C00N C00F 105.75(13) . . ?
F006 C00N H00A 111.1(9) . . ?
F006 C00N H00B 107.3(12) . . ?
C00F C00N H00A 112.3(9) . . ?
C00F C00N H00B 115.7(12) . . ?
H00A C00N H00B 104.7(14) . . ?
C00E C00O H00O 119.9 . . ?
C00K C00O C00E 120.18(15) . . ?
C00K C00O H00O 119.9 . . ?
S002 C00P H00C 109.5 . . ?
S002 C00P H00D 109.5 . . ?
S002 C00P H00G 109.5 . . ?
H00C C00P H00D 109.5 . . ?
H00C C00P H00G 109.5 . . ?
H00D C00P H00G 109.5 . . ?
C00L C00Q H00Q 120.6 . . ?
C00L C00Q C00R 118.72(16) . . ?
C00R C00Q H00Q 120.6 . . ?
C00H C00R C00Q 120.63(16) . . ?
C00H C00R H00R 119.7 . . ?
C00Q C00R H00R 119.7 . . ?

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
S001 N00B C00F C00H 102.39(13) . . . . ?
S001 N00B C00F C00N -127.22(12) . . . . ?
S002 N00B C00F C00H -61.11(15) . . . . ?
S002 N00B C00F C00N 69.27(15) . . . . ?
F003 C00L C00M C00I -178.37(14) . . . . ?
F003 C00L C00Q C00R 178.73(16) . . . . ?
O004 S001 N00B S002 166.10(8) . . . . ?
O004 S001 N00B C00F 2.21(12) . . . . ?
O004 S001 C00G C00D 26.89(14) . . . . ?
O004 S001 C00G C00E -143.16(12) . . . . ?
O005 S001 N00B S002 37.11(10) . . . . ?
O005 S001 N00B C00F -126.78(11) . . . . ?
O005 S001 C00G C00D 156.01(12) . . . . ?
O005 S001 C00G C00E -14.04(14) . . . . ?
O007 S002 N00B S001 37.92(10) . . . . ?
O007 S002 N00B C00F -158.40(11) . . . . ?
O008 S002 N00B S001 166.43(8) . . . . ?
O008 S002 N00B C00F -29.89(12) . . . . ?
O009 N00C C00D C00G -131.12(15) . . . . ?
O009 N00C C00D C00J 49.95(19) . . . . ?
O00A N00C C00D C00G 51.3(2) . . . . ?
O00A N00C C00D C00J -127.59(16) . . . . ?
N00B S001 C00G C00D -88.45(13) . . . . ?
N00B S001 C00G C00E 101.50(12) . . . . ?
N00B C00F C00H C00I -75.05(17) . . . . ?
N00B C00F C00H C00R 102.72(18) . . . . ?
N00B C00F C00N F006 158.51(13) . . . . ?
N00C C00D C00G S001 10.9(2) . . . . ?
N00C C00D C00G C00E -179.08(13) . . . . ?
N00C C00D C00J C00K 178.41(14) . . . . ?
C00D C00J C00K C00O 0.6(2) . . . . ?
C00F C00H C00I C00M 176.38(14) . . . . ?
C00F C00H C00R C00Q -175.90(17) . . . . ?
C00G S001 N00B S002 -77.86(9) . . . . ?
C00G S001 N00B C00F 118.26(11) . . . . ?
C00G C00D C00J C00K -0.5(2) . . . . ?
C00G C00E C00O C00K -0.7(2) . . . . ?
C00H C00F C00N F006 -73.41(17) . . . . ?
C00H C00I C00M C00L 0.0(2) . . . . ?
C00I C00H C00R C00Q 1.9(3) . . . . ?
C00J C00D C00G S001 -170.21(12) . . . . ?
C00J C00D C00G C00E -0.2(2) . . . . ?
C00J C00K C00O C00E 0.0(2) . . . . ?
C00L C00Q C00R C00H -0.7(3) . . . . ?
C00M C00L C00Q C00R -0.9(3) . . . . ?
C00N C00F C00H C00I 156.90(14) . . . . ?
C00N C00F C00H C00R -25.3(2) . . . . ?
C00O C00E C00G S001 171.38(12) . . . . ?
C00O C00E C00G C00D 0.8(2) . . . . ?
C00P S002 N00B S001 -78.10(10) . . . . ?
C00P S002 N00B C00F 85.59(12) . . . . ?
C00Q C00L C00M C00I 1.3(3) . . . . ?
C00R C00H C00I C00M -1.5(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
;
####################################################################### 
# 
# 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_3aa_auto
_audit_block_doi                 10.5517/ccdc.csd.cc2f02p7
_database_code_depnum_ccdc_archive 'CCDC 2234408'
loop_
_audit_author_name
_audit_author_address
'Kohsuke Aikawa'
;The University of Tokyo
Japan
;
_audit_update_record             
;
2023-05-02 deposited with the CCDC.	2023-06-22 downloaded from the CCDC.
;
_audit_creation_date             2021-04-29
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H15 F2 N3 O8 S2'
_chemical_formula_sum            'C20 H15 F2 N3 O8 S2'
_chemical_formula_weight         527.47
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   16.5286(5)
_cell_length_b                   8.3039(2)
_cell_length_c                   16.6083(5)
_cell_angle_alpha                90
_cell_angle_beta                 108.130(3)
_cell_angle_gamma                90
_cell_volume                     2166.35(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    13763
_cell_measurement_temperature    169.98(10)
_cell_measurement_theta_max      30.6300
_cell_measurement_theta_min      2.1280
_shelx_estimated_absorpt_T_max   0.982
_shelx_estimated_absorpt_T_min   0.891
_exptl_absorpt_coefficient_mu    0.319
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98483
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.99a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.617
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1080
_exptl_crystal_size_max          0.371
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.056
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0300
_diffrn_reflns_av_unetI/netI     0.0254
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            41398
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.607
_diffrn_reflns_theta_min         2.581
_diffrn_ambient_temperature      170.15
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -71.00  -3.00   0.50   18.50    --   20.00  54.00  86.78  136
  2  ω      2.00 104.00   0.50   18.50    --   20.00  54.00  86.78  204
  3  ω    -74.00  98.00   0.50   18.50    --   20.00  54.00-120.00  344
  4  ω    -73.00 -35.00   0.50   18.50    --   20.00  54.00  -2.78   76
  5  ω    -26.00   1.00   0.50   18.50    --   20.00  54.00  -2.78   54
  6  ω     26.00  51.00   0.50   18.50    --   20.00  54.00  -2.78   50
  7  ω     68.00 107.00   0.50   18.50    --   20.00  54.00  -2.78   78
  8  ω    -74.00  64.00   0.50   18.50    --   20.00  54.00-150.00  276
  9  ω     81.00 106.00   0.50   18.50    --   20.00  54.00-150.00   50
 10  ω    -70.00 -44.00   0.50   18.50    --   20.00  54.00 -60.00   52
 11  ω    -31.00  -5.00   0.50   18.50    --   20.00  54.00 -60.00   52
 12  ω     20.00  51.00   0.50   18.50    --   20.00  54.00 -60.00   62
 13  ω     60.00  85.00   0.50   18.50    --   20.00  54.00 -60.00   50
 14  ω    -67.00 -16.00   0.50   18.50    --   20.00  54.00  60.00  102
 15  ω     56.00  81.00   0.50   18.50    --   20.00  54.00  60.00   50
 16  ω    -67.00 -18.00   0.50   18.50    --   20.00  54.00  30.00   98
 17  ω    -70.00 -43.00   0.50   18.50    --   20.00  54.00-180.00   54
 18  ω    -13.00  12.00   0.50   18.50    --   20.00  54.00-180.00   50
 19  ω     15.00  49.00   0.50   18.50    --   20.00  54.00-180.00   68
 20  ω    -29.00  -4.00   0.50   18.50    --   20.00  54.00 -90.00   50
 21  ω     19.00  44.00   0.50   18.50    --   20.00  54.00 -90.00   50
 22  ω    -70.00  45.00   0.50   18.50    --   20.00  54.00 146.72  230
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini II'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5066
_reflns_number_total             6519
_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 1.171.41.99a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.99a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.99a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         1.231
_refine_diff_density_min         -0.409
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     316
_refine_ls_number_reflns         6519
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0554
_refine_ls_R_factor_gt           0.0389
_refine_ls_restrained_S_all      1.031
_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)+(0.0540P)²+1.0522P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1016
_refine_ls_wR_factor_ref         0.1087
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C00Q(H00Q)
2.b Secondary CH2 refined with riding coordinates:
 C00W(H00A,H00B)
2.c Aromatic/amide H refined with riding coordinates:
 C00H(H00H), C00J(H00J), C00M(H00M), C00N(H00N), C00P(H00P), C00R(H00R),
 C00S(H00S), C00T(H00T), C00U(H00U), C00V(H00V), C00X(H00X), C00Z(H00Z)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S001 S 0.81074(2) 0.53437(4) 0.45239(2) 0.02029(9) Uani 1 1 d . . . . .
S002 S 0.62570(2) 0.53157(4) 0.40270(2) 0.02081(9) Uani 1 1 d . . . . .
O003 O 0.63397(7) 0.42857(14) 0.33709(7) 0.0265(2) Uani 1 1 d . . . . .
F004 F 0.70044(9) 0.24615(13) 0.54335(7) 0.0450(3) Uani 1 1 d . . . . .
O005 O 0.79211(7) 0.61787(13) 0.37401(7) 0.0254(2) Uani 1 1 d . . . . .
O006 O 0.56580(8) 0.49737(16) 0.44599(8) 0.0312(3) Uani 1 1 d . . . . .
O007 O 0.87640(7) 0.58936(15) 0.52506(7) 0.0287(3) Uani 1 1 d . . . . .
F008 F 0.63725(10) 1.09757(16) 0.70276(10) 0.0618(4) Uani 1 1 d . . . . .
O009 O 0.47999(9) 0.63767(19) 0.15362(9) 0.0460(4) Uani 1 1 d . . . . .
O00A O 0.46280(9) 0.54006(18) 0.26781(10) 0.0446(4) Uani 1 1 d . . . . .
O00B O 0.88323(10) 0.2991(2) 0.63162(9) 0.0476(4) Uani 1 1 d . . . . .
N00C N 0.72025(8) 0.53852(15) 0.47870(8) 0.0209(2) Uani 1 1 d . . . . .
N00D N 0.49457(9) 0.63424(18) 0.23038(9) 0.0297(3) Uani 1 1 d . . . . .
O00E O 1.00123(10) 0.2858(2) 0.60273(10) 0.0581(5) Uani 1 1 d . . . . .
N00F N 0.92394(10) 0.27560(19) 0.58389(9) 0.0344(4) Uani 1 1 d . . . . .
C00G C 0.83197(9) 0.33088(18) 0.43373(9) 0.0210(3) Uani 1 1 d . . . . .
C00H C 0.80134(10) 0.27520(19) 0.35065(10) 0.0232(3) Uani 1 1 d . . . . .
H00H H 0.770580 0.345752 0.306761 0.028 Uiso 1 1 calc R U . . .
C00I C 0.55101(9) 0.76062(19) 0.28010(10) 0.0222(3) Uani 1 1 d . . . . .
C00J C 0.65107(10) 0.85980(19) 0.40694(10) 0.0230(3) Uani 1 1 d . . . . .
H00J H 0.689686 0.842863 0.462098 0.028 Uiso 1 1 calc R U . . .
C00K C 0.60748(9) 0.73028(17) 0.36095(9) 0.0196(3) Uani 1 1 d . . . . .
C00L C 0.70007(10) 0.67742(19) 0.60598(10) 0.0241(3) Uani 1 1 d . . . . .
C00M C 0.75964(11) 0.7995(2) 0.63468(10) 0.0264(3) Uani 1 1 d . . . . .
H00M H 0.815710 0.784846 0.631903 0.032 Uiso 1 1 calc R U . . .
C00N C 0.81558(10) 0.1174(2) 0.33181(11) 0.0267(3) Uani 1 1 d . . . . .
H00N H 0.794841 0.080747 0.274869 0.032 Uiso 1 1 calc R U . . .
C00O C 0.87977(10) 0.2252(2) 0.49569(10) 0.0243(3) Uani 1 1 d . . . . .
C00P C 0.63886(11) 1.0144(2) 0.37318(11) 0.0261(3) Uani 1 1 d . . . . .
H00P H 0.667115 1.102937 0.406417 0.031 Uiso 1 1 calc R U . . .
C00Q C 0.72697(11) 0.52522(19) 0.57179(10) 0.0247(3) Uani 1 1 d . . . . .
H00Q H 0.789121 0.513262 0.602626 0.030 Uiso 1 1 calc R U . . .
C00R C 0.73926(12) 0.9416(2) 0.66717(11) 0.0315(4) Uani 1 1 d . . . . .
H00R H 0.780281 1.024699 0.686401 0.038 Uiso 1 1 calc R U . . .
C00S C 0.54161(11) 0.9121(2) 0.24491(10) 0.0275(3) Uani 1 1 d . . . . .
H00S H 0.504913 0.928748 0.188854 0.033 Uiso 1 1 calc R U . . .
C00T C 0.89279(11) 0.0673(2) 0.47723(11) 0.0294(3) Uani 1 1 d . . . . .
H00T H 0.924285 -0.003361 0.520678 0.035 Uiso 1 1 calc R U . . .
C00U C 0.85944(11) 0.0128(2) 0.39462(11) 0.0293(3) Uani 1 1 d . . . . .
H00U H 0.866814 -0.096375 0.381348 0.035 Uiso 1 1 calc R U . . .
C00V C 0.58601(11) 1.0402(2) 0.29174(11) 0.0286(3) Uani 1 1 d . . . . .
H00V H 0.580073 1.145211 0.267901 0.034 Uiso 1 1 calc R U . . .
C00W C 0.68530(14) 0.3721(2) 0.59166(11) 0.0353(4) Uani 1 1 d . . . . .
H00A H 0.709220 0.345947 0.652643 0.042 Uiso 1 1 calc R U . . .
H00B H 0.623235 0.388982 0.578483 0.042 Uiso 1 1 calc R U . . .
C00X C 0.61882(13) 0.6998(3) 0.61106(14) 0.0415(5) Uani 1 1 d . . . . .
H00X H 0.577272 0.617644 0.592013 0.050 Uiso 1 1 calc R U . . .
C00Y C 0.65836(14) 0.9588(2) 0.67072(13) 0.0393(4) Uani 1 1 d . . . . .
C00Z C 0.59775(14) 0.8420(3) 0.64388(17) 0.0523(6) Uani 1 1 d . . . . .
H00Z H 0.542087 0.857639 0.647592 0.063 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
S001 O005 1.4214(12) . ?
S001 O007 1.4241(11) . ?
S001 N00C 1.6840(13) . ?
S001 C00G 1.7726(15) . ?
S002 O003 1.4249(12) . ?
S002 O006 1.4215(12) . ?
S002 N00C 1.6767(13) . ?
S002 C00K 1.7789(15) . ?
F004 C00W 1.388(2) . ?
F008 C00Y 1.359(2) . ?
O009 N00D 1.222(2) . ?
O00A N00D 1.215(2) . ?
O00B N00F 1.205(2) . ?
N00C C00Q 1.5191(19) . ?
N00D C00I 1.474(2) . ?
O00E N00F 1.220(2) . ?
N00F C00O 1.479(2) . ?
C00G C00H 1.392(2) . ?
C00G C00O 1.395(2) . ?
C00H H00H 0.9500 . ?
C00H C00N 1.385(2) . ?
C00I C00K 1.399(2) . ?
C00I C00S 1.375(2) . ?
C00J H00J 0.9500 . ?
C00J C00K 1.384(2) . ?
C00J C00P 1.391(2) . ?
C00L C00M 1.390(2) . ?
C00L C00Q 1.508(2) . ?
C00L C00X 1.384(2) . ?
C00M H00M 0.9500 . ?
C00M C00R 1.383(2) . ?
C00N H00N 0.9500 . ?
C00N C00U 1.377(2) . ?
C00O C00T 1.379(2) . ?
C00P H00P 0.9500 . ?
C00P C00V 1.379(2) . ?
C00Q H00Q 1.0000 . ?
C00Q C00W 1.530(2) . ?
C00R H00R 0.9500 . ?
C00R C00Y 1.364(3) . ?
C00S H00S 0.9500 . ?
C00S C00V 1.386(2) . ?
C00T H00T 0.9500 . ?
C00T C00U 1.386(2) . ?
C00U H00U 0.9500 . ?
C00V H00V 0.9500 . ?
C00W H00A 0.9900 . ?
C00W H00B 0.9900 . ?
C00X H00X 0.9500 . ?
C00X C00Z 1.389(3) . ?
C00Y C00Z 1.366(3) . ?
C00Z H00Z 0.9500 . ?

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
O005 S001 O007 120.69(7) . . ?
O005 S001 N00C 105.72(7) . . ?
O005 S001 C00G 107.65(7) . . ?
O007 S001 N00C 106.12(7) . . ?
O007 S001 C00G 108.28(7) . . ?
N00C S001 C00G 107.76(7) . . ?
O003 S002 N00C 107.91(7) . . ?
O003 S002 C00K 107.67(7) . . ?
O006 S002 O003 120.97(8) . . ?
O006 S002 N00C 105.01(7) . . ?
O006 S002 C00K 108.81(7) . . ?
N00C S002 C00K 105.46(7) . . ?
S002 N00C S001 119.93(8) . . ?
C00Q N00C S001 118.23(10) . . ?
C00Q N00C S002 121.30(10) . . ?
O009 N00D C00I 116.92(16) . . ?
O00A N00D O009 124.91(16) . . ?
O00A N00D C00I 118.05(14) . . ?
O00B N00F O00E 125.08(16) . . ?
O00B N00F C00O 119.53(16) . . ?
O00E N00F C00O 115.36(15) . . ?
C00H C00G S001 117.32(11) . . ?
C00H C00G C00O 118.02(14) . . ?
C00O C00G S001 124.61(12) . . ?
C00G C00H H00H 119.9 . . ?
C00N C00H C00G 120.22(15) . . ?
C00N C00H H00H 119.9 . . ?
C00K C00I N00D 121.75(14) . . ?
C00S C00I N00D 116.41(14) . . ?
C00S C00I C00K 121.73(14) . . ?
C00K C00J H00J 119.7 . . ?
C00K C00J C00P 120.63(15) . . ?
C00P C00J H00J 119.7 . . ?
C00I C00K S002 121.51(11) . . ?
C00J C00K S002 120.64(11) . . ?
C00J C00K C00I 117.83(14) . . ?
C00M C00L C00Q 118.67(15) . . ?
C00X C00L C00M 118.57(16) . . ?
C00X C00L C00Q 122.76(15) . . ?
C00L C00M H00M 119.2 . . ?
C00R C00M C00L 121.60(16) . . ?
C00R C00M H00M 119.2 . . ?
C00H C00N H00N 119.6 . . ?
C00U C00N C00H 120.79(15) . . ?
C00U C00N H00N 119.6 . . ?
C00G C00O N00F 122.97(14) . . ?
C00T C00O N00F 115.22(14) . . ?
C00T C00O C00G 121.72(15) . . ?
C00J C00P H00P 119.8 . . ?
C00V C00P C00J 120.45(15) . . ?
C00V C00P H00P 119.8 . . ?
N00C C00Q H00Q 105.5 . . ?
N00C C00Q C00W 112.62(13) . . ?
C00L C00Q N00C 112.67(13) . . ?
C00L C00Q H00Q 105.5 . . ?
C00L C00Q C00W 114.19(14) . . ?
C00W C00Q H00Q 105.5 . . ?
C00M C00R H00R 121.1 . . ?
C00Y C00R C00M 117.85(16) . . ?
C00Y C00R H00R 121.1 . . ?
C00I C00S H00S 120.2 . . ?
C00I C00S C00V 119.58(15) . . ?
C00V C00S H00S 120.2 . . ?
C00O C00T H00T 120.4 . . ?
C00O C00T C00U 119.29(15) . . ?
C00U C00T H00T 120.4 . . ?
C00N C00U C00T 119.84(15) . . ?
C00N C00U H00U 120.1 . . ?
C00T C00U H00U 120.1 . . ?
C00P C00V C00S 119.63(15) . . ?
C00P C00V H00V 120.2 . . ?
C00S C00V H00V 120.2 . . ?
F004 C00W C00Q 109.11(15) . . ?
F004 C00W H00A 109.9 . . ?
F004 C00W H00B 109.9 . . ?
C00Q C00W H00A 109.9 . . ?
C00Q C00W H00B 109.9 . . ?
H00A C00W H00B 108.3 . . ?
C00L C00X H00X 119.8 . . ?
C00L C00X C00Z 120.32(17) . . ?
C00Z C00X H00X 119.8 . . ?
F008 C00Y C00R 118.68(18) . . ?
F008 C00Y C00Z 118.58(18) . . ?
C00R C00Y C00Z 122.74(18) . . ?
C00X C00Z H00Z 120.5 . . ?
C00Y C00Z C00X 118.92(18) . . ?
C00Y C00Z H00Z 120.5 . . ?

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
S001 N00C C00Q C00L 113.36(13) . . . . ?
S001 N00C C00Q C00W -115.71(14) . . . . ?
S001 C00G C00H C00N -179.86(12) . . . . ?
S001 C00G C00O N00F -4.7(2) . . . . ?
S001 C00G C00O C00T 178.93(13) . . . . ?
S002 N00C C00Q C00L -75.09(15) . . . . ?
S002 N00C C00Q C00W 55.85(18) . . . . ?
O003 S002 N00C S001 35.82(11) . . . . ?
O003 S002 N00C C00Q -135.59(12) . . . . ?
O003 S002 C00K C00I 43.39(14) . . . . ?
O003 S002 C00K C00J -134.66(13) . . . . ?
O005 S001 N00C S002 33.80(10) . . . . ?
O005 S001 N00C C00Q -154.53(11) . . . . ?
O005 S001 C00G C00H -20.52(14) . . . . ?
O005 S001 C00G C00O 156.89(14) . . . . ?
O006 S002 N00C S001 166.10(9) . . . . ?
O006 S002 N00C C00Q -5.31(13) . . . . ?
O006 S002 C00K C00I -89.38(14) . . . . ?
O006 S002 C00K C00J 92.58(14) . . . . ?
O007 S001 N00C S002 163.09(8) . . . . ?
O007 S001 N00C C00Q -25.23(13) . . . . ?
O007 S001 C00G C00H -152.52(12) . . . . ?
O007 S001 C00G C00O 24.89(16) . . . . ?
F008 C00Y C00Z C00X 180.0(2) . . . . ?
O009 N00D C00I C00K -145.30(16) . . . . ?
O009 N00D C00I C00S 38.4(2) . . . . ?
O00A N00D C00I C00K 38.3(2) . . . . ?
O00A N00D C00I C00S -137.97(17) . . . . ?
O00B N00F C00O C00G 75.0(2) . . . . ?
O00B N00F C00O C00T -108.37(19) . . . . ?
N00C S001 C00G C00H 93.09(13) . . . . ?
N00C S001 C00G C00O -89.50(15) . . . . ?
N00C S002 C00K C00I 158.41(12) . . . . ?
N00C S002 C00K C00J -19.63(14) . . . . ?
N00C C00Q C00W F004 37.7(2) . . . . ?
N00D C00I C00K S002 9.0(2) . . . . ?
N00D C00I C00K C00J -172.86(14) . . . . ?
N00D C00I C00S C00V 173.24(15) . . . . ?
O00E N00F C00O C00G -106.9(2) . . . . ?
O00E N00F C00O C00T 69.8(2) . . . . ?
N00F C00O C00T C00U -175.00(16) . . . . ?
C00G S001 N00C S002 -81.09(10) . . . . ?
C00G S001 N00C C00Q 90.58(12) . . . . ?
C00G C00H C00N C00U 0.5(2) . . . . ?
C00G C00O C00T C00U 1.7(3) . . . . ?
C00H C00G C00O N00F 172.73(15) . . . . ?
C00H C00G C00O C00T -3.7(2) . . . . ?
C00H C00N C00U C00T -2.6(3) . . . . ?
C00I C00S C00V C00P -0.2(3) . . . . ?
C00J C00P C00V C00S 3.2(3) . . . . ?
C00K S002 N00C S001 -79.03(10) . . . . ?
C00K S002 N00C C00Q 109.55(12) . . . . ?
C00K C00I C00S C00V -3.0(2) . . . . ?
C00K C00J C00P C00V -3.0(2) . . . . ?
C00L C00M C00R C00Y 0.3(3) . . . . ?
C00L C00Q C00W F004 167.84(14) . . . . ?
C00L C00X C00Z C00Y 0.2(4) . . . . ?
C00M C00L C00Q N00C -85.09(18) . . . . ?
C00M C00L C00Q C00W 144.77(16) . . . . ?
C00M C00L C00X C00Z 0.3(3) . . . . ?
C00M C00R C00Y F008 179.77(18) . . . . ?
C00M C00R C00Y C00Z 0.2(3) . . . . ?
C00O C00G C00H C00N 2.6(2) . . . . ?
C00O C00T C00U C00N 1.5(3) . . . . ?
C00P C00J C00K S002 177.91(12) . . . . ?
C00P C00J C00K C00I -0.2(2) . . . . ?
C00Q C00L C00M C00R -179.66(15) . . . . ?
C00Q C00L C00X C00Z 179.38(19) . . . . ?
C00R C00Y C00Z C00X -0.4(4) . . . . ?
C00S C00I C00K S002 -174.88(13) . . . . ?
C00S C00I C00K C00J 3.2(2) . . . . ?
C00X C00L C00M C00R -0.5(3) . . . . ?
C00X C00L C00Q N00C 95.8(2) . . . . ?
C00X C00L C00Q C00W -34.3(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
;
####################################################################### 
# 
# 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_3fa_auto
_audit_block_doi                 10.5517/ccdc.csd.cc2f02r9
_database_code_depnum_ccdc_archive 'CCDC 2234410'
loop_
_audit_author_name
_audit_author_address
'Kohsuke Aikawa'
;The University of Tokyo
Japan
;
_audit_update_record             
;
2023-05-02 deposited with the CCDC.	2023-06-22 downloaded from the CCDC.
;
_audit_creation_date             2022-01-04
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H15 F2 N3 O8 S2'
_chemical_formula_sum            'C20 H15 F2 N3 O8 S2'
_chemical_formula_weight         527.47
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   10.0255(3)
_cell_length_b                   10.1690(4)
_cell_length_c                   21.2063(9)
_cell_angle_alpha                90
_cell_angle_beta                 91.882(3)
_cell_angle_gamma                90
_cell_volume                     2160.80(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    19818
_cell_measurement_temperature    169.99(10)
_cell_measurement_theta_max      30.7180
_cell_measurement_theta_min      2.0290
_shelx_estimated_absorpt_T_max   0.910
_shelx_estimated_absorpt_T_min   0.822
_exptl_absorpt_coefficient_mu    0.319
_exptl_absorpt_correction_T_max  0.842
_exptl_absorpt_correction_T_min  0.736
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.99a (Rigaku Oxford Diffraction, 2021)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.621
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1080
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
4 -14 0 0.1573
9 -9 -14 0.2370
-1 -14 9 0.1580
-6 -10 18 0.2198
-10 -3 21 0.2960
-11 2 20 0.3219
-12 -2 -15 0.1375
3 -3 -29 0.2723
9 -3 -23 0.3060
13 2 13 0.1685
10 2 19 0.1538
8 3 24 0.1646
0 3 29 0.2609
-1 14 -5 0.1490

_exptl_crystal_size_max          0.64
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.3
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0302
_diffrn_reflns_av_unetI/netI     0.0170
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            36386
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.370
_diffrn_reflns_theta_min         1.922
_diffrn_ambient_temperature      170.15
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -73.00  65.00   0.50    6.20    --   20.00  54.00-172.56  276
  2  ω    -73.00  35.00   0.50    6.20    --   20.00  54.00 -60.00  216
  3  ω     77.00 108.00   0.50    6.20    --   20.00  54.00 -60.00   62
  4  ω    -70.00  75.00   0.50    6.20    --   20.00  54.00 120.00  290
  5  ω    -69.00  49.00   0.50    6.20    --   20.00  54.00-120.00  236
  6  ω     76.00 101.00   0.50    6.20    --   20.00  54.00-120.00   50
  7  ω    -64.00  -5.00   0.50    6.20    --   20.00  54.00 -30.00  118
  8  ω     78.00 103.00   0.50    6.20    --   20.00  54.00 -30.00   50
  9  ω    -62.00  86.00   0.50    6.20    --   20.00  54.00-150.00  296
 10  ω    -64.00  13.00   0.50    6.20    --   20.00  54.00   0.00  154
 11  ω     50.00  75.00   0.50    6.20    --   20.00  54.00   0.00   50
 12  ω    -42.00 -17.00   0.50    6.20    --   20.00  54.00 -90.00   50
 13  ω      8.00  33.00   0.50    6.20    --   20.00  54.00 -90.00   50
 14  ω     43.00  69.00   0.50    6.20    --   20.00  54.00 -90.00   52
 15  ω    -74.00 -46.00   0.50    6.20    --   20.00  54.00  90.00   56
 16  ω     39.00  64.00   0.50    6.20    --   20.00  54.00  90.00   50
 17  ω    -67.00 -40.00   0.50    6.20    --   20.00  54.00  30.00   54
 18  ω     40.00  65.00   0.50    6.20    --   20.00  54.00  30.00   50
 19  ω    -64.00  37.00   0.50    6.20    --   20.00  54.00 150.00  202
 20  ω     72.00  97.00   0.50    6.20    --   20.00  54.00  39.28   50
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini II'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3888
_reflns_number_total             4416
_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 1.171.41.99a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.99a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.99a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.624
_refine_diff_density_min         -0.470
_refine_diff_density_rms         0.099
_refine_ls_extinction_coef       0.0021(6)
_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   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     317
_refine_ls_number_reflns         4416
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0389
_refine_ls_R_factor_gt           0.0338
_refine_ls_restrained_S_all      1.052
_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)+(0.0501P)²+1.4407P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0932
_refine_ls_wR_factor_ref         0.0965
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C00N(H00N)
2.b Secondary CH2 refined with riding coordinates:
 C00T(H00A,H00B)
2.c Aromatic/amide H refined with riding coordinates:
 C00I(H00I), C00M(H00M), C00O(H00O), C00P(H00P), C00Q(H00Q), C00R(H00R),
 C00S(H00S), C00U(H00U), C00W(H00W), C00X(H00X), C00Y(H00Y), C00Z(H00Z)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S001 S 0.28283(4) 0.47274(4) 0.66433(2) 0.02290(12) Uani 1 1 d . . . . .
S002 S 0.26400(4) 0.67764(4) 0.75953(2) 0.02166(12) Uani 1 1 d . . . . .
F003 F 0.59396(11) 0.52823(14) 0.75841(6) 0.0451(3) Uani 1 1 d . . . . .
O004 O 0.14589(12) 0.49983(13) 0.64807(6) 0.0294(3) Uani 1 1 d . . . . .
O005 O 0.23945(13) 0.74741(13) 0.70207(6) 0.0305(3) Uani 1 1 d . . . . .
F006 F -0.00443(14) 0.30153(16) 0.95759(6) 0.0540(4) Uani 1 1 d . . . . .
O007 O 0.35854(12) 0.72585(13) 0.80562(7) 0.0310(3) Uani 1 1 d . . . . .
O008 O 0.33104(13) 0.34099(12) 0.66515(6) 0.0296(3) Uani 1 1 d . . . . .
O009 O 0.17874(14) 0.93156(13) 0.82965(7) 0.0345(3) Uani 1 1 d . . . . .
O00A O 0.72625(14) 0.71472(16) 0.47325(7) 0.0412(4) Uani 1 1 d . . . . .
N00B N 0.31606(14) 0.52897(14) 0.73871(7) 0.0211(3) Uani 1 1 d . . . . .
N00C N 0.15579(15) 0.84839(16) 0.86890(7) 0.0289(3) Uani 1 1 d . . . . .
O00D O 0.56906(17) 0.85727(18) 0.45642(8) 0.0517(4) Uani 1 1 d . . . . .
N00E N 0.61539(17) 0.75883(17) 0.48236(7) 0.0335(4) Uani 1 1 d . . . . .
O00F O 0.1895(2) 0.8558(2) 0.92438(7) 0.0650(6) Uani 1 1 d . . . . .
C00G C 0.07628(17) 0.73334(16) 0.84916(8) 0.0223(3) Uani 1 1 d . . . . .
C00H C 0.11025(16) 0.65538(16) 0.79801(8) 0.0207(3) Uani 1 1 d . . . . .
C00I C 0.02364(17) 0.55485(17) 0.77978(8) 0.0245(4) Uani 1 1 d . . . . .
H00I H 0.044261 0.499932 0.745192 0.029 Uiso 1 1 calc R U . . .
C00J C 0.29135(17) 0.39639(17) 0.83636(8) 0.0256(4) Uani 1 1 d . . . . .
C00K C 0.53347(18) 0.69102(19) 0.52887(8) 0.0274(4) Uani 1 1 d . . . . .
C00L C 0.38282(17) 0.56454(18) 0.61337(8) 0.0240(4) Uani 1 1 d . . . . .
C00M C -0.03713(17) 0.71088(17) 0.88243(8) 0.0258(4) Uani 1 1 d . . . . .
H00M H -0.056380 0.763439 0.918034 0.031 Uiso 1 1 calc R U . . .
C00N C 0.38658(17) 0.43792(18) 0.78583(8) 0.0255(4) Uani 1 1 d . . . . .
H00N H 0.407664 0.356160 0.761927 0.031 Uiso 1 1 calc R U . . .
C00O C -0.09334(18) 0.53415(18) 0.81198(9) 0.0285(4) Uani 1 1 d . . . . .
H00O H -0.153383 0.466758 0.798484 0.034 Uiso 1 1 calc R U . . .
C00P C 0.27610(19) 0.46827(19) 0.89135(9) 0.0296(4) Uani 1 1 d . . . . .
H00P H 0.334071 0.540006 0.900809 0.036 Uiso 1 1 calc R U . . .
C00Q C 0.59334(18) 0.59541(19) 0.56598(8) 0.0280(4) Uani 1 1 d . . . . .
H00Q H 0.684898 0.574133 0.561821 0.034 Uiso 1 1 calc R U . . .
C00R C -0.12260(17) 0.61085(18) 0.86334(9) 0.0289(4) Uani 1 1 d . . . . .
H00R H -0.201646 0.594913 0.885635 0.035 Uiso 1 1 calc R U . . .
C00S C 0.51687(17) 0.53102(18) 0.60951(9) 0.0269(4) Uani 1 1 d . . . . .
H00S H 0.555158 0.465195 0.636237 0.032 Uiso 1 1 calc R U . . .
C00T C 0.51991(18) 0.4919(2) 0.81021(9) 0.0330(4) Uani 1 1 d . . . . .
H00A H 0.505549 0.569180 0.837576 0.040 Uiso 1 1 calc R U . . .
H00B H 0.568492 0.424100 0.835338 0.040 Uiso 1 1 calc R U . . .
C00U C 0.32325(18) 0.6606(2) 0.57546(9) 0.0326(4) Uani 1 1 d . . . . .
H00U H 0.231298 0.681072 0.578869 0.039 Uiso 1 1 calc R U . . .
C00V C 0.0953(2) 0.3305(2) 0.91805(10) 0.0367(5) Uani 1 1 d . . . . .
C00W C 0.1763(2) 0.4356(2) 0.93264(9) 0.0352(4) Uani 1 1 d . . . . .
H00W H 0.164457 0.485055 0.970068 0.042 Uiso 1 1 calc R U . . .
C00X C 0.4005(2) 0.7261(2) 0.53260(9) 0.0343(4) Uani 1 1 d . . . . .
H00X H 0.363280 0.793416 0.506409 0.041 Uiso 1 1 calc R U . . .
C00Y C 0.20949(19) 0.28767(19) 0.82443(9) 0.0310(4) Uani 1 1 d . . . . .
H00Y H 0.222067 0.236127 0.787743 0.037 Uiso 1 1 calc R U . . .
C00Z C 0.1099(2) 0.2537(2) 0.86540(10) 0.0365(5) Uani 1 1 d . . . . .
H00Z H 0.053791 0.179881 0.857317 0.044 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
S001 O004 1.4313(13) . ?
S001 O008 1.4243(13) . ?
S001 N00B 1.7005(15) . ?
S001 C00L 1.7649(18) . ?
S002 O005 1.4243(13) . ?
S002 O007 1.4259(13) . ?
S002 N00B 1.6638(14) . ?
S002 C00H 1.7821(16) . ?
F003 C00T 1.395(2) . ?
F006 C00V 1.358(2) . ?
O009 N00C 1.214(2) . ?
O00A N00E 1.220(2) . ?
N00B C00N 1.520(2) . ?
N00C O00F 1.216(2) . ?
N00C C00G 1.469(2) . ?
O00D N00E 1.226(2) . ?
N00E C00K 1.475(2) . ?
C00G C00H 1.395(2) . ?
C00G C00M 1.377(2) . ?
C00H C00I 1.388(2) . ?
C00I H00I 0.9500 . ?
C00I C00O 1.392(2) . ?
C00J C00N 1.518(2) . ?
C00J C00P 1.389(3) . ?
C00J C00Y 1.395(3) . ?
C00K C00Q 1.376(3) . ?
C00K C00X 1.385(3) . ?
C00L C00S 1.391(2) . ?
C00L C00U 1.388(3) . ?
C00M H00M 0.9500 . ?
C00M C00R 1.382(3) . ?
C00N H00N 1.0000 . ?
C00N C00T 1.520(3) . ?
C00O H00O 0.9500 . ?
C00O C00R 1.379(3) . ?
C00P H00P 0.9500 . ?
C00P C00W 1.391(3) . ?
C00Q H00Q 0.9500 . ?
C00Q C00S 1.384(3) . ?
C00R H00R 0.9500 . ?
C00S H00S 0.9500 . ?
C00T H00A 0.9900 . ?
C00T H00B 0.9900 . ?
C00U H00U 0.9500 . ?
C00U C00X 1.384(3) . ?
C00V C00W 1.372(3) . ?
C00V C00Z 1.374(3) . ?
C00W H00W 0.9500 . ?
C00X H00X 0.9500 . ?
C00Y H00Y 0.9500 . ?
C00Y C00Z 1.389(3) . ?
C00Z H00Z 0.9500 . ?

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
O004 S001 N00B 108.42(7) . . ?
O004 S001 C00L 108.08(8) . . ?
O008 S001 O004 120.43(8) . . ?
O008 S001 N00B 104.41(7) . . ?
O008 S001 C00L 107.80(8) . . ?
N00B S001 C00L 106.99(8) . . ?
O005 S002 O007 120.50(8) . . ?
O005 S002 N00B 105.81(8) . . ?
O005 S002 C00H 109.10(8) . . ?
O007 S002 N00B 106.68(7) . . ?
O007 S002 C00H 107.17(8) . . ?
N00B S002 C00H 106.84(8) . . ?
S002 N00B S001 119.87(8) . . ?
C00N N00B S001 118.55(11) . . ?
C00N N00B S002 121.49(11) . . ?
O009 N00C O00F 124.58(17) . . ?
O009 N00C C00G 118.22(15) . . ?
O00F N00C C00G 117.13(16) . . ?
O00A N00E O00D 124.26(17) . . ?
O00A N00E C00K 117.66(17) . . ?
O00D N00E C00K 118.06(17) . . ?
C00H C00G N00C 122.02(15) . . ?
C00M C00G N00C 115.83(15) . . ?
C00M C00G C00H 122.08(16) . . ?
C00G C00H S002 121.39(13) . . ?
C00I C00H S002 120.57(13) . . ?
C00I C00H C00G 117.95(15) . . ?
C00H C00I H00I 119.9 . . ?
C00H C00I C00O 120.27(16) . . ?
C00O C00I H00I 119.9 . . ?
C00P C00J C00N 122.36(17) . . ?
C00P C00J C00Y 119.27(17) . . ?
C00Y C00J C00N 118.19(16) . . ?
C00Q C00K N00E 118.08(16) . . ?
C00Q C00K C00X 123.50(17) . . ?
C00X C00K N00E 118.42(17) . . ?
C00S C00L S001 118.40(14) . . ?
C00U C00L S001 118.99(13) . . ?
C00U C00L C00S 122.44(16) . . ?
C00G C00M H00M 120.4 . . ?
C00G C00M C00R 119.11(16) . . ?
C00R C00M H00M 120.4 . . ?
N00B C00N H00N 105.9 . . ?
N00B C00N C00T 112.86(15) . . ?
C00J C00N N00B 110.11(13) . . ?
C00J C00N H00N 105.9 . . ?
C00J C00N C00T 115.27(15) . . ?
C00T C00N H00N 105.9 . . ?
C00I C00O H00O 119.8 . . ?
C00R C00O C00I 120.41(17) . . ?
C00R C00O H00O 119.8 . . ?
C00J C00P H00P 119.9 . . ?
C00J C00P C00W 120.28(18) . . ?
C00W C00P H00P 119.9 . . ?
C00K C00Q H00Q 120.8 . . ?
C00K C00Q C00S 118.36(16) . . ?
C00S C00Q H00Q 120.8 . . ?
C00M C00R H00R 119.9 . . ?
C00O C00R C00M 120.12(16) . . ?
C00O C00R H00R 119.9 . . ?
C00L C00S H00S 120.6 . . ?
C00Q C00S C00L 118.73(17) . . ?
C00Q C00S H00S 120.6 . . ?
F003 C00T C00N 108.21(15) . . ?
F003 C00T H00A 110.1 . . ?
F003 C00T H00B 110.1 . . ?
C00N C00T H00A 110.1 . . ?
C00N C00T H00B 110.1 . . ?
H00A C00T H00B 108.4 . . ?
C00L C00U H00U 120.7 . . ?
C00X C00U C00L 118.66(17) . . ?
C00X C00U H00U 120.7 . . ?
F006 C00V C00W 118.16(19) . . ?
F006 C00V C00Z 118.57(19) . . ?
C00W C00V C00Z 123.26(19) . . ?
C00P C00W H00W 120.8 . . ?
C00V C00W C00P 118.45(19) . . ?
C00V C00W H00W 120.8 . . ?
C00K C00X H00X 120.8 . . ?
C00U C00X C00K 118.30(18) . . ?
C00U C00X H00X 120.8 . . ?
C00J C00Y H00Y 119.5 . . ?
C00Z C00Y C00J 120.98(18) . . ?
C00Z C00Y H00Y 119.5 . . ?
C00V C00Z C00Y 117.68(19) . . ?
C00V C00Z H00Z 121.2 . . ?
C00Y C00Z H00Z 121.2 . . ?

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
S001 N00B C00N C00J -110.45(14) . . . . ?
S001 N00B C00N C00T 119.18(14) . . . . ?
S001 C00L C00S C00Q 174.85(14) . . . . ?
S001 C00L C00U C00X -175.72(16) . . . . ?
S002 N00B C00N C00J 66.12(17) . . . . ?
S002 N00B C00N C00T -64.24(18) . . . . ?
S002 C00H C00I C00O 176.97(14) . . . . ?
O004 S001 N00B S002 -45.65(11) . . . . ?
O004 S001 N00B C00N 130.98(12) . . . . ?
O004 S001 C00L C00S -164.54(14) . . . . ?
O004 S001 C00L C00U 10.87(18) . . . . ?
O005 S002 N00B S001 -19.83(11) . . . . ?
O005 S002 N00B C00N 163.64(12) . . . . ?
O005 S002 C00H C00G -102.32(15) . . . . ?
O005 S002 C00H C00I 81.04(16) . . . . ?
F006 C00V C00W C00P -178.10(17) . . . . ?
F006 C00V C00Z C00Y 177.81(18) . . . . ?
O007 S002 N00B S001 -149.28(9) . . . . ?
O007 S002 N00B C00N 34.19(14) . . . . ?
O007 S002 C00H C00G 29.68(16) . . . . ?
O007 S002 C00H C00I -146.96(14) . . . . ?
O008 S001 N00B S002 -175.20(9) . . . . ?
O008 S001 N00B C00N 1.44(14) . . . . ?
O008 S001 C00L C00S -32.91(17) . . . . ?
O008 S001 C00L C00U 142.50(15) . . . . ?
O009 N00C C00G C00H 53.5(2) . . . . ?
O009 N00C C00G C00M -123.63(18) . . . . ?
O00A N00E C00K C00Q 9.7(3) . . . . ?
O00A N00E C00K C00X -169.83(18) . . . . ?
N00B S001 C00L C00S 78.89(16) . . . . ?
N00B S001 C00L C00U -105.70(16) . . . . ?
N00B S002 C00H C00G 143.72(14) . . . . ?
N00B S002 C00H C00I -32.92(16) . . . . ?
N00B C00N C00T F003 -50.9(2) . . . . ?
N00C C00G C00H S002 8.2(2) . . . . ?
N00C C00G C00H C00I -175.09(16) . . . . ?
N00C C00G C00M C00R 174.83(16) . . . . ?
O00D N00E C00K C00Q -168.72(18) . . . . ?
O00D N00E C00K C00X 11.7(3) . . . . ?
N00E C00K C00Q C00S -179.71(16) . . . . ?
N00E C00K C00X C00U 178.82(18) . . . . ?
O00F N00C C00G C00H -129.4(2) . . . . ?
O00F N00C C00G C00M 53.5(2) . . . . ?
C00G C00H C00I C00O 0.2(3) . . . . ?
C00G C00M C00R C00O 0.6(3) . . . . ?
C00H S002 N00B S001 96.34(10) . . . . ?
C00H S002 N00B C00N -80.19(14) . . . . ?
C00H C00G C00M C00R -2.3(3) . . . . ?
C00H C00I C00O C00R -1.8(3) . . . . ?
C00I C00O C00R C00M 1.4(3) . . . . ?
C00J C00N C00T F003 -178.60(15) . . . . ?
C00J C00P C00W C00V 0.8(3) . . . . ?
C00J C00Y C00Z C00V -0.2(3) . . . . ?
C00K C00Q C00S C00L 0.7(3) . . . . ?
C00L S001 N00B S002 70.69(11) . . . . ?
C00L S001 N00B C00N -112.67(13) . . . . ?
C00L C00U C00X C00K 1.0(3) . . . . ?
C00M C00G C00H S002 -174.90(13) . . . . ?
C00M C00G C00H C00I 1.8(3) . . . . ?
C00N C00J C00P C00W 172.10(17) . . . . ?
C00N C00J C00Y C00Z -172.61(17) . . . . ?
C00P C00J C00N N00B -89.0(2) . . . . ?
C00P C00J C00N C00T 40.1(2) . . . . ?
C00P C00J C00Y C00Z 2.6(3) . . . . ?
C00Q C00K C00X C00U -0.7(3) . . . . ?
C00S C00L C00U C00X -0.5(3) . . . . ?
C00U C00L C00S C00Q -0.4(3) . . . . ?
C00W C00V C00Z C00Y -1.9(3) . . . . ?
C00X C00K C00Q C00S -0.2(3) . . . . ?
C00Y C00J C00N N00B 86.05(19) . . . . ?
C00Y C00J C00N C00T -144.88(17) . . . . ?
C00Y C00J C00P C00W -2.9(3) . . . . ?
C00Z C00V C00W C00P 1.6(3) . . . . ?

_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
;
