# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_190612f
_database_code_depnum_ccdc_archive 'CCDC 1940975'
loop_
_audit_author_name
_audit_author_address
Cheney
;Wuhan University of Technology
China
;
_audit_update_record             
;
2019-07-16 deposited with the CCDC.	2020-06-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C7 H13 Cl F N O4 S2'
_chemical_formula_weight         293.75

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   14.829(12)
_cell_length_b                   5.526(5)
_cell_length_c                   18.143(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 127.47(4)
_cell_angle_gamma                90.00
_cell_volume                     1180.0(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1174
_cell_measurement_theta_min      2.243
_cell_measurement_theta_max      20.416

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.654
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             608
_exptl_absorpt_coefficient_mu    0.689
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8577
_exptl_absorpt_correction_T_max  0.9730
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            2082
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0751
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.25
_diffrn_reflns_theta_max         25.02
_reflns_number_total             2082
_reflns_number_gt                1394
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0930P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2082
_refine_ls_number_parameters     146
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1001
_refine_ls_R_factor_gt           0.0779
_refine_ls_wR_factor_ref         0.1930
_refine_ls_wR_factor_gt          0.1805
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_restrained_S_all      1.089
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.1403(2) 0.6549(4) 0.11956(15) 0.0883(8) Uani 1 1 d . . .
F1 F 0.5556(4) 0.3662(12) 0.6892(4) 0.125(2) Uani 1 1 d . . .
N1 N 0.2380(4) 0.4236(9) 0.4004(3) 0.0474(12) Uani 1 1 d . . .
O1 O 0.2158(4) 0.7439(7) 0.4799(3) 0.0666(13) Uani 1 1 d . . .
O2 O 0.0486(4) 0.5288(9) 0.3548(4) 0.0735(15) Uani 1 1 d . . .
O3 O 0.5285(6) -0.0464(15) 0.6862(5) 0.129(3) Uani 1 1 d . . .
O4 O 0.5796(5) 0.1317(12) 0.5958(4) 0.0960(18) Uani 1 1 d . . .
S1 S 0.16457(15) 0.5249(2) 0.43296(13) 0.0514(5) Uani 1 1 d . . .
S2 S 0.51913(16) 0.1457(4) 0.63178(14) 0.0693(6) Uani 1 1 d . . .
C1 C 0.1881(6) 0.3128(12) 0.5139(5) 0.0565(17) Uani 1 1 d . . .
H1A H 0.1543 0.3687 0.5428 0.068 Uiso 1 1 calc R . .
H1B H 0.1527 0.1604 0.4830 0.068 Uiso 1 1 calc R . .
C2 C 0.3170(6) 0.2753(14) 0.5889(5) 0.0624(18) Uani 1 1 d . . .
H2A H 0.3508 0.4237 0.6240 0.075 Uiso 1 1 calc R . .
H2B H 0.3296 0.1496 0.6315 0.075 Uiso 1 1 calc R . .
C3 C 0.3737(5) 0.2045(11) 0.5454(4) 0.0497(15) Uani 1 1 d . . .
H3 H 0.3385 0.0534 0.5112 0.060 Uiso 1 1 calc R . .
C4 C 0.3582(5) 0.3908(12) 0.4763(4) 0.0501(15) Uani 1 1 d . . .
H4A H 0.3910 0.5440 0.5077 0.060 Uiso 1 1 calc R . .
H4B H 0.3974 0.3368 0.4518 0.060 Uiso 1 1 calc R . .
C5 C 0.1862(6) 0.2425(11) 0.3257(4) 0.0533(15) Uani 1 1 d . . .
H5A H 0.1070 0.2200 0.2997 0.064 Uiso 1 1 calc R . .
H5B H 0.2248 0.0887 0.3508 0.064 Uiso 1 1 calc R . .
C6 C 0.1941(6) 0.3236(11) 0.2500(5) 0.0565(16) Uani 1 1 d . . .
H6A H 0.2729 0.3566 0.2770 0.068 Uiso 1 1 calc R . .
H6B H 0.1676 0.1947 0.2049 0.068 Uiso 1 1 calc R . .
C7 C 0.1250(8) 0.5446(13) 0.2027(6) 0.074(2) Uani 1 1 d . . .
H7A H 0.1480 0.6694 0.2486 0.088 Uiso 1 1 calc R . .
H7B H 0.0456 0.5080 0.1723 0.088 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C7 1.764(7) . ?
F1 S2 1.476(6) . ?
N1 C4 1.455(8) . ?
N1 C5 1.470(8) . ?
N1 S1 1.622(5) . ?
O1 S1 1.407(5) . ?
O2 S1 1.414(5) . ?
O3 S2 1.398(6) . ?
O4 S2 1.396(6) . ?
S1 C1 1.740(6) . ?
S2 C3 1.761(7) . ?
C1 C2 1.544(9) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.513(9) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.527(8) . ?
C3 H3 0.9800 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.516(9) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.486(9) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?

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
C4 N1 C5 116.1(5) . . ?
C4 N1 S1 113.9(4) . . ?
C5 N1 S1 118.7(4) . . ?
O1 S1 O2 118.3(3) . . ?
O1 S1 N1 106.4(3) . . ?
O2 S1 N1 108.5(3) . . ?
O1 S1 C1 108.1(3) . . ?
O2 S1 C1 110.7(3) . . ?
N1 S1 C1 103.9(3) . . ?
O4 S2 O3 118.2(5) . . ?
O4 S2 F1 108.2(4) . . ?
O3 S2 F1 107.0(5) . . ?
O4 S2 C3 112.4(4) . . ?
O3 S2 C3 108.1(4) . . ?
F1 S2 C3 101.6(3) . . ?
C2 C1 S1 109.8(4) . . ?
C2 C1 H1A 109.7 . . ?
S1 C1 H1A 109.7 . . ?
C2 C1 H1B 109.7 . . ?
S1 C1 H1B 109.7 . . ?
H1A C1 H1B 108.2 . . ?
C3 C2 C1 111.0(5) . . ?
C3 C2 H2A 109.4 . . ?
C1 C2 H2A 109.4 . . ?
C3 C2 H2B 109.4 . . ?
C1 C2 H2B 109.4 . . ?
H2A C2 H2B 108.0 . . ?
C2 C3 C4 113.5(5) . . ?
C2 C3 S2 110.6(4) . . ?
C4 C3 S2 110.3(4) . . ?
C2 C3 H3 107.4 . . ?
C4 C3 H3 107.4 . . ?
S2 C3 H3 107.4 . . ?
N1 C4 C3 110.3(5) . . ?
N1 C4 H4A 109.6 . . ?
C3 C4 H4A 109.6 . . ?
N1 C4 H4B 109.6 . . ?
C3 C4 H4B 109.6 . . ?
H4A C4 H4B 108.1 . . ?
N1 C5 C6 110.4(5) . . ?
N1 C5 H5A 109.6 . . ?
C6 C5 H5A 109.6 . . ?
N1 C5 H5B 109.6 . . ?
C6 C5 H5B 109.6 . . ?
H5A C5 H5B 108.1 . . ?
C7 C6 C5 111.1(5) . . ?
C7 C6 H6A 109.4 . . ?
C5 C6 H6A 109.4 . . ?
C7 C6 H6B 109.4 . . ?
C5 C6 H6B 109.4 . . ?
H6A C6 H6B 108.0 . . ?
C6 C7 Cl1 112.1(5) . . ?
C6 C7 H7A 109.2 . . ?
Cl1 C7 H7A 109.2 . . ?
C6 C7 H7B 109.2 . . ?
Cl1 C7 H7B 109.2 . . ?
H7A C7 H7B 107.9 . . ?

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
C4 N1 S1 O1 56.8(5) . . . . ?
C5 N1 S1 O1 -160.8(4) . . . . ?
C4 N1 S1 O2 -175.0(4) . . . . ?
C5 N1 S1 O2 -32.6(5) . . . . ?
C4 N1 S1 C1 -57.2(5) . . . . ?
C5 N1 S1 C1 85.2(5) . . . . ?
O1 S1 C1 C2 -60.0(5) . . . . ?
O2 S1 C1 C2 169.0(5) . . . . ?
N1 S1 C1 C2 52.7(6) . . . . ?
S1 C1 C2 C3 -55.5(7) . . . . ?
C1 C2 C3 C4 58.8(7) . . . . ?
C1 C2 C3 S2 -176.7(5) . . . . ?
O4 S2 C3 C2 -166.9(5) . . . . ?
O3 S2 C3 C2 60.9(6) . . . . ?
F1 S2 C3 C2 -51.5(6) . . . . ?
O4 S2 C3 C4 -40.5(6) . . . . ?
O3 S2 C3 C4 -172.7(5) . . . . ?
F1 S2 C3 C4 74.9(5) . . . . ?
C5 N1 C4 C3 -81.7(6) . . . . ?
S1 N1 C4 C3 61.7(6) . . . . ?
C2 C3 C4 N1 -60.3(7) . . . . ?
S2 C3 C4 N1 175.0(4) . . . . ?
C4 N1 C5 C6 -91.0(6) . . . . ?
S1 N1 C5 C6 127.4(5) . . . . ?
N1 C5 C6 C7 -65.6(7) . . . . ?
C5 C6 C7 Cl1 176.0(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.737
_refine_diff_density_min         -0.476
_refine_diff_density_rms         0.144
####################################################################### 
# 
# 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_190914d
_database_code_depnum_ccdc_archive 'CCDC 1953896'
loop_
_audit_author_name
_audit_author_address
Cheney 'Wuhan University of Technology'
_audit_update_record             
;
2019-09-16 deposited with the CCDC.	2020-06-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H16 F N O4 S2'
_chemical_formula_weight         273.34

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   12.6609(11)
_cell_length_b                   10.4865(9)
_cell_length_c                   9.8417(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.188(2)
_cell_angle_gamma                90.00
_cell_volume                     1296.40(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2410
_cell_measurement_theta_min      2.477
_cell_measurement_theta_max      26.178

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.32
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             576
_exptl_absorpt_coefficient_mu    0.422
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8329
_exptl_absorpt_correction_T_max  0.8768
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6247
_diffrn_reflns_av_R_equivalents  0.0347
_diffrn_reflns_av_sigmaI/netI    0.0384
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.53
_diffrn_reflns_theta_max         25.02
_reflns_number_total             2287
_reflns_number_gt                1624
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0586P)²+0.9817P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2287
_refine_ls_number_parameters     155
_refine_ls_number_restraints     24
_refine_ls_R_factor_all          0.0774
_refine_ls_R_factor_gt           0.0483
_refine_ls_wR_factor_ref         0.1404
_refine_ls_wR_factor_gt          0.1216
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.080
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.2906(3) 0.3103(3) 0.4377(3) 0.1083(10) Uani 1 1 d . . .
N1 N 0.7515(2) 0.3653(3) 0.2132(3) 0.0614(8) Uani 1 1 d . A .
O1 O 0.6238(2) 0.4237(2) 0.0031(2) 0.0672(7) Uani 1 1 d . . .
O2 O 0.6197(2) 0.5530(2) 0.2045(3) 0.0701(7) Uani 1 1 d . . .
O3 O 0.2001(2) 0.4187(4) 0.2483(3) 0.1049(12) Uani 1 1 d . . .
O4 O 0.3329(3) 0.5255(3) 0.3991(3) 0.0886(9) Uani 1 1 d . . .
S1 S 0.64078(6) 0.43258(7) 0.14811(8) 0.0446(3) Uani 1 1 d . . .
S2 S 0.29837(8) 0.41080(10) 0.33243(10) 0.0649(3) Uani 1 1 d . . .
C1 C 0.7027(3) 0.2860(3) 0.3121(4) 0.0530(8) Uani 1 1 d . . .
H1A H 0.7124 0.3210 0.4041 0.064 Uiso 1 1 calc R . .
H1B H 0.7266 0.1981 0.3133 0.064 Uiso 1 1 calc R . .
C2 C 0.5878(3) 0.3028(3) 0.2397(3) 0.0488(8) Uani 1 1 d . . .
H2 H 0.5669 0.2309 0.1786 0.059 Uiso 1 1 calc R . .
C3 C 0.5018(3) 0.3353(3) 0.3256(3) 0.0517(8) Uani 1 1 d . . .
H3A H 0.5204 0.4135 0.3756 0.062 Uiso 1 1 calc R . .
H3B H 0.4962 0.2679 0.3917 0.062 Uiso 1 1 calc R . .
C4 C 0.3954(2) 0.3521(3) 0.2379(3) 0.0496(8) Uani 1 1 d . . .
H4A H 0.3723 0.2706 0.1981 0.060 Uiso 1 1 calc R . .
H4B H 0.4037 0.4105 0.1636 0.060 Uiso 1 1 calc R . .
C5 C 0.8608(3) 0.4148(4) 0.2305(4) 0.0625(10) Uani 1 1 d D . .
C6 C 0.9339(5) 0.3006(7) 0.2497(9) 0.116(2) Uani 0.847(7) 1 d PDU A 1
H6A H 1.0066 0.3289 0.2625 0.175 Uiso 0.847(7) 1 calc PR A 1
H6B H 0.9224 0.2471 0.1701 0.175 Uiso 0.847(7) 1 calc PR A 1
H6C H 0.9192 0.2533 0.3287 0.175 Uiso 0.847(7) 1 calc PR A 1
C7 C 0.8776(5) 0.4883(7) 0.1019(6) 0.093(2) Uani 0.847(7) 1 d PDU A 1
H7A H 0.8259 0.5555 0.0872 0.140 Uiso 0.847(7) 1 calc PR A 1
H7B H 0.8697 0.4317 0.0247 0.140 Uiso 0.847(7) 1 calc PR A 1
H7C H 0.9479 0.5244 0.1126 0.140 Uiso 0.847(7) 1 calc PR A 1
C8 C 0.8742(5) 0.5054(7) 0.3521(6) 0.100(2) Uani 0.847(7) 1 d PDU A 1
H8A H 0.8615 0.4602 0.4334 0.150 Uiso 0.847(7) 1 calc PR A 1
H8B H 0.8242 0.5742 0.3360 0.150 Uiso 0.847(7) 1 calc PR A 1
H8C H 0.9453 0.5390 0.3637 0.150 Uiso 0.847(7) 1 calc PR A 1
C6' C 0.901(3) 0.314(4) 0.132(5) 0.116(2) Uani 0.153(7) 1 d PD A 2
H6'1 H 0.9776 0.3153 0.1417 0.175 Uiso 0.153(7) 1 calc PR A 2
H6'2 H 0.8733 0.3333 0.0395 0.175 Uiso 0.153(7) 1 calc PR A 2
H6'3 H 0.8775 0.2305 0.1557 0.175 Uiso 0.153(7) 1 calc PR A 2
C7' C 0.871(3) 0.547(4) 0.158(4) 0.093(2) Uani 0.153(7) 1 d PD A 2
H7'1 H 0.8489 0.6144 0.2141 0.140 Uiso 0.153(7) 1 calc PR A 2
H7'2 H 0.8273 0.5477 0.0708 0.140 Uiso 0.153(7) 1 calc PR A 2
H7'3 H 0.9441 0.5611 0.1436 0.140 Uiso 0.153(7) 1 calc PR A 2
C8' C 0.924(3) 0.400(4) 0.372(3) 0.100(2) Uani 0.153(7) 1 d PD A 2
H8'1 H 0.8819 0.4318 0.4401 0.150 Uiso 0.153(7) 1 calc PR A 2
H8'2 H 0.9886 0.4482 0.3765 0.150 Uiso 0.153(7) 1 calc PR A 2
H8'3 H 0.9399 0.3120 0.3895 0.150 Uiso 0.153(7) 1 calc PR A 2


_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
F1 S2 1.490(3) . ?
N1 C5 1.468(4) . ?
N1 C1 1.474(4) . ?
N1 S1 1.627(3) . ?
O1 S1 1.419(2) . ?
O2 S1 1.418(2) . ?
O3 S2 1.408(3) . ?
O4 S2 1.413(3) . ?
S1 C2 1.808(3) . ?
S2 C4 1.743(3) . ?
C1 C2 1.548(4) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.498(5) . ?
C2 H2 0.9800 . ?
C3 C4 1.517(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.511(7) . ?
C5 C7 1.519(7) . ?
C5 C8 1.521(7) . ?
C5 C8' 1.53(3) . ?
C5 C6' 1.56(4) . ?
C5 C7' 1.58(4) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C6' H6'1 0.9600 . ?
C6' H6'2 0.9600 . ?
C6' H6'3 0.9600 . ?
C7' H7'1 0.9600 . ?
C7' H7'2 0.9600 . ?
C7' H7'3 0.9600 . ?
C8' H8'1 0.9600 . ?
C8' H8'2 0.9600 . ?
C8' H8'3 0.9600 . ?

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
C5 N1 C1 126.2(3) . . ?
C5 N1 S1 130.2(3) . . ?
C1 N1 S1 95.4(2) . . ?
O2 S1 O1 116.09(16) . . ?
O2 S1 N1 115.27(17) . . ?
O1 S1 N1 112.47(16) . . ?
O2 S1 C2 112.08(16) . . ?
O1 S1 C2 115.65(15) . . ?
N1 S1 C2 80.34(15) . . ?
O3 S2 O4 115.0(2) . . ?
O3 S2 F1 108.7(2) . . ?
O4 S2 F1 108.82(18) . . ?
O3 S2 C4 109.68(18) . . ?
O4 S2 C4 110.53(18) . . ?
F1 S2 C4 103.50(16) . . ?
N1 C1 C2 94.5(2) . . ?
N1 C1 H1A 112.8 . . ?
C2 C1 H1A 112.8 . . ?
N1 C1 H1B 112.8 . . ?
C2 C1 H1B 112.8 . . ?
H1A C1 H1B 110.3 . . ?
C3 C2 C1 118.3(3) . . ?
C3 C2 S1 116.8(2) . . ?
C1 C2 S1 85.96(19) . . ?
C3 C2 H2 111.2 . . ?
C1 C2 H2 111.2 . . ?
S1 C2 H2 111.2 . . ?
C2 C3 C4 111.2(3) . . ?
C2 C3 H3A 109.4 . . ?
C4 C3 H3A 109.4 . . ?
C2 C3 H3B 109.4 . . ?
C4 C3 H3B 109.4 . . ?
H3A C3 H3B 108.0 . . ?
C3 C4 S2 111.9(2) . . ?
C3 C4 H4A 109.2 . . ?
S2 C4 H4A 109.2 . . ?
C3 C4 H4B 109.2 . . ?
S2 C4 H4B 109.2 . . ?
H4A C4 H4B 107.9 . . ?
N1 C5 C6 106.8(4) . . ?
N1 C5 C7 108.1(3) . . ?
C6 C5 C7 111.0(5) . . ?
N1 C5 C8 108.8(4) . . ?
C6 C5 C8 113.0(5) . . ?
C7 C5 C8 109.0(4) . . ?
N1 C5 C8' 116.5(13) . . ?
C6 C5 C8' 64.3(17) . . ?
C7 C5 C8' 134.5(13) . . ?
C8 C5 C8' 49.3(17) . . ?
N1 C5 C6' 93.8(14) . . ?
C6 C5 C6' 45.3(16) . . ?
C7 C5 C6' 74.9(16) . . ?
C8 C5 C6' 153.8(15) . . ?
C8' C5 C6' 109(2) . . ?
N1 C5 C7' 113.0(15) . . ?
C6 C5 C7' 132.1(15) . . ?
C7 C5 C7' 31.3(14) . . ?
C8 C5 C7' 78.4(15) . . ?
C8' C5 C7' 116(2) . . ?
C6' C5 C7' 105(2) . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C5 C7 H7A 109.5 . . ?
C5 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C5 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C5 C8 H8A 109.5 . . ?
C5 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C5 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C5 C6' H6'1 109.5 . . ?
C5 C6' H6'2 109.5 . . ?
H6'1 C6' H6'2 109.5 . . ?
C5 C6' H6'3 109.5 . . ?
H6'1 C6' H6'3 109.5 . . ?
H6'2 C6' H6'3 109.5 . . ?
C5 C7' H7'1 109.5 . . ?
C5 C7' H7'2 109.5 . . ?
H7'1 C7' H7'2 109.5 . . ?
C5 C7' H7'3 109.5 . . ?
H7'1 C7' H7'3 109.5 . . ?
H7'2 C7' H7'3 109.5 . . ?
C5 C8' H8'1 109.5 . . ?
C5 C8' H8'2 109.5 . . ?
H8'1 C8' H8'2 109.5 . . ?
C5 C8' H8'3 109.5 . . ?
H8'1 C8' H8'3 109.5 . . ?
H8'2 C8' H8'3 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 S1 O2 -53.1(4) . . . . ?
C1 N1 S1 O2 95.7(2) . . . . ?
C5 N1 S1 O1 83.1(4) . . . . ?
C1 N1 S1 O1 -128.1(2) . . . . ?
C5 N1 S1 C2 -163.0(4) . . . . ?
C1 N1 S1 C2 -14.2(2) . . . . ?
C5 N1 C1 C2 167.2(3) . . . . ?
S1 N1 C1 C2 16.5(2) . . . . ?
N1 C1 C2 C3 -133.1(3) . . . . ?
N1 C1 C2 S1 -14.8(2) . . . . ?
O2 S1 C2 C3 19.8(3) . . . . ?
O1 S1 C2 C3 -116.4(3) . . . . ?
N1 S1 C2 C3 133.3(3) . . . . ?
O2 S1 C2 C1 -100.0(2) . . . . ?
O1 S1 C2 C1 123.9(2) . . . . ?
N1 S1 C2 C1 13.5(2) . . . . ?
C1 C2 C3 C4 178.3(3) . . . . ?
S1 C2 C3 C4 77.8(3) . . . . ?
C2 C3 C4 S2 -171.9(2) . . . . ?
O3 S2 C4 C3 -177.1(3) . . . . ?
O4 S2 C4 C3 55.1(3) . . . . ?
F1 S2 C4 C3 -61.3(3) . . . . ?
C1 N1 C5 C6 58.9(6) . . . . ?
S1 N1 C5 C6 -160.8(4) . . . . ?
C1 N1 C5 C7 178.4(4) . . . . ?
S1 N1 C5 C7 -41.3(5) . . . . ?
C1 N1 C5 C8 -63.4(5) . . . . ?
S1 N1 C5 C8 77.0(5) . . . . ?
C1 N1 C5 C8' -10(2) . . . . ?
S1 N1 C5 C8' 130(2) . . . . ?
C1 N1 C5 C6' 103.1(17) . . . . ?
S1 N1 C5 C6' -116.6(17) . . . . ?
C1 N1 C5 C7' -148.5(17) . . . . ?
S1 N1 C5 C7' -8.1(17) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.427
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.057
####################################################################### 
# 
# 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_190831a
_database_code_depnum_ccdc_archive 'CCDC 1951376'
loop_
_audit_author_name
_audit_author_address
Chen
;Wuhan University of technology
China
;
_audit_update_record             
;
2019-09-04 deposited with the CCDC.	2020-06-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H15 F N2 O5 S2'
_chemical_formula_weight         350.38

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   14.0641(12)
_cell_length_b                   9.2583(8)
_cell_length_c                   12.1126(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.973(3)
_cell_angle_gamma                90.00
_cell_volume                     1536.9(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1906
_cell_measurement_theta_min      2.655
_cell_measurement_theta_max      23.609

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.514
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             728
_exptl_absorpt_coefficient_mu    0.381
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8382
_exptl_absorpt_correction_T_max  0.9593
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7407
_diffrn_reflns_av_R_equivalents  0.0511
_diffrn_reflns_av_sigmaI/netI    0.1237
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.65
_diffrn_reflns_theta_max         25.02
_reflns_number_total             2694
_reflns_number_gt                1819
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0000P)²+0.9393P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2694
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0954
_refine_ls_R_factor_gt           0.0561
_refine_ls_wR_factor_ref         0.1842
_refine_ls_wR_factor_gt          0.1493
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_restrained_S_all      1.095
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.1199(2) 0.7361(4) 0.4309(3) 0.1102(13) Uani 1 1 d . . .
N1 N 0.5793(2) 0.6596(3) 0.3582(3) 0.0425(8) Uani 1 1 d . . .
N2 N 0.5926(2) 0.7442(4) 0.4581(3) 0.0467(9) Uani 1 1 d . . .
H2 H 0.6060 0.6869 0.5196 0.056 Uiso 1 1 d R . .
O1 O 0.62892(19) 0.5941(3) 0.2024(3) 0.0498(7) Uani 1 1 d . . .
O2 O 0.4245(2) 0.6345(3) 0.2005(2) 0.0556(8) Uani 1 1 d . . .
O3 O 0.4579(2) 0.4516(3) 0.3476(3) 0.0585(8) Uani 1 1 d . . .
O4 O 0.1824(3) 0.8647(5) 0.6008(4) 0.1087(15) Uani 1 1 d . . .
O5 O 0.2565(3) 0.6377(4) 0.5596(4) 0.1009(14) Uani 1 1 d . . .
S1 S 0.46328(7) 0.59858(9) 0.31492(8) 0.0374(3) Uani 1 1 d . . .
S2 S 0.21208(9) 0.77201(17) 0.52360(12) 0.0712(5) Uani 1 1 d . . .
C1 C 0.6449(3) 0.6619(4) 0.2893(3) 0.0407(9) Uani 1 1 d . . .
C2 C 0.7361(3) 0.7508(5) 0.3335(4) 0.0569(12) Uani 1 1 d . . .
H2C H 0.7180 0.8517 0.3355 0.068 Uiso 1 1 calc R . .
H2D H 0.7652 0.7210 0.4105 0.068 Uiso 1 1 calc R . .
C3 C 0.8096(3) 0.7354(5) 0.2631(4) 0.0495(11) Uani 1 1 d . . .
C4 C 0.8693(4) 0.6158(6) 0.2715(5) 0.0744(15) Uani 1 1 d . . .
H4 H 0.8643 0.5424 0.3224 0.089 Uiso 1 1 calc R . .
C5 C 0.9370(4) 0.6047(9) 0.2040(7) 0.101(2) Uani 1 1 d . . .
H5 H 0.9774 0.5242 0.2097 0.121 Uiso 1 1 calc R . .
C6 C 0.9439(5) 0.7124(12) 0.1292(7) 0.112(3) Uani 1 1 d . . .
H6 H 0.9885 0.7045 0.0833 0.135 Uiso 1 1 calc R . .
C7 C 0.8868(5) 0.8296(9) 0.1216(6) 0.102(2) Uani 1 1 d . . .
H7 H 0.8927 0.9028 0.0710 0.123 Uiso 1 1 calc R . .
C8 C 0.8201(4) 0.8425(6) 0.1872(5) 0.0731(14) Uani 1 1 d . . .
H8 H 0.7812 0.9246 0.1808 0.088 Uiso 1 1 calc R . .
C9 C 0.5010(3) 0.8196(4) 0.4521(4) 0.0447(10) Uani 1 1 d . . .
H9A H 0.4948 0.8991 0.3989 0.054 Uiso 1 1 calc R . .
H9B H 0.4988 0.8583 0.5259 0.054 Uiso 1 1 calc R . .
C10 C 0.4180(3) 0.7122(4) 0.4135(4) 0.0460(10) Uani 1 1 d . . .
H10 H 0.4118 0.6533 0.4787 0.055 Uiso 1 1 calc R . .
C11 C 0.3200(3) 0.7727(5) 0.3603(4) 0.0536(11) Uani 1 1 d . . .
H11A H 0.2753 0.6939 0.3334 0.064 Uiso 1 1 calc R . .
H11B H 0.3252 0.8310 0.2954 0.064 Uiso 1 1 calc R . .
C12 C 0.2787(3) 0.8651(5) 0.4430(4) 0.0528(11) Uani 1 1 d . . .
H12A H 0.2373 0.9391 0.4003 0.063 Uiso 1 1 calc R . .
H12B H 0.3325 0.9135 0.4937 0.063 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 S2 1.549(4) . ?
N1 C1 1.376(5) . ?
N1 N2 1.418(4) . ?
N1 S1 1.695(3) . ?
N2 C9 1.453(5) . ?
N2 H2 0.9000 . ?
O1 C1 1.203(4) . ?
O2 S1 1.410(3) . ?
O3 S1 1.424(3) . ?
O4 S2 1.401(4) . ?
O5 S2 1.416(4) . ?
S1 C10 1.811(4) . ?
S2 C12 1.728(4) . ?
C1 C2 1.517(6) . ?
C2 C3 1.488(6) . ?
C2 H2C 0.9700 . ?
C2 H2D 0.9700 . ?
C3 C4 1.379(6) . ?
C3 C8 1.383(7) . ?
C4 C5 1.391(9) . ?
C4 H4 0.9300 . ?
C5 C6 1.365(10) . ?
C5 H5 0.9300 . ?
C6 C7 1.341(11) . ?
C6 H6 0.9300 . ?
C7 C8 1.363(8) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C9 C10 1.525(5) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.493(6) . ?
C10 H10 0.9800 . ?
C11 C12 1.527(6) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 N2 122.1(3) . . ?
C1 N1 S1 123.2(3) . . ?
N2 N1 S1 112.4(2) . . ?
N1 N2 C9 106.1(3) . . ?
N1 N2 H2 110.1 . . ?
C9 N2 H2 110.1 . . ?
O2 S1 O3 117.75(19) . . ?
O2 S1 N1 111.04(16) . . ?
O3 S1 N1 109.86(18) . . ?
O2 S1 C10 113.26(19) . . ?
O3 S1 C10 108.86(19) . . ?
N1 S1 C10 93.39(17) . . ?
O4 S2 O5 120.6(3) . . ?
O4 S2 F1 106.8(2) . . ?
O5 S2 F1 105.9(3) . . ?
O4 S2 C12 110.7(2) . . ?
O5 S2 C12 110.7(2) . . ?
F1 S2 C12 99.8(2) . . ?
O1 C1 N1 120.2(3) . . ?
O1 C1 C2 124.7(4) . . ?
N1 C1 C2 115.0(3) . . ?
C3 C2 C1 112.7(4) . . ?
C3 C2 H2C 109.0 . . ?
C1 C2 H2C 109.0 . . ?
C3 C2 H2D 109.0 . . ?
C1 C2 H2D 109.0 . . ?
H2C C2 H2D 107.8 . . ?
C4 C3 C8 118.1(5) . . ?
C4 C3 C2 121.6(4) . . ?
C8 C3 C2 120.3(4) . . ?
C3 C4 C5 120.1(6) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C6 C5 C4 119.8(6) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
C7 C6 C5 120.4(6) . . ?
C7 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C6 C7 C8 120.7(7) . . ?
C6 C7 H7 119.6 . . ?
C8 C7 H7 119.6 . . ?
C7 C8 C3 121.0(6) . . ?
C7 C8 H8 119.5 . . ?
C3 C8 H8 119.5 . . ?
N2 C9 C10 108.1(3) . . ?
N2 C9 H9A 110.1 . . ?
C10 C9 H9A 110.1 . . ?
N2 C9 H9B 110.1 . . ?
C10 C9 H9B 110.1 . . ?
H9A C9 H9B 108.4 . . ?
C11 C10 C9 117.2(3) . . ?
C11 C10 S1 111.1(3) . . ?
C9 C10 S1 102.9(3) . . ?
C11 C10 H10 108.4 . . ?
C9 C10 H10 108.4 . . ?
S1 C10 H10 108.4 . . ?
C10 C11 C12 112.1(4) . . ?
C10 C11 H11A 109.2 . . ?
C12 C11 H11A 109.2 . . ?
C10 C11 H11B 109.2 . . ?
C12 C11 H11B 109.2 . . ?
H11A C11 H11B 107.9 . . ?
C11 C12 S2 115.2(3) . . ?
C11 C12 H12A 108.5 . . ?
S2 C12 H12A 108.5 . . ?
C11 C12 H12B 108.5 . . ?
S2 C12 H12B 108.5 . . ?
H12A C12 H12B 107.5 . . ?

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
C1 N1 N2 C9 130.0(4) . . . . ?
S1 N1 N2 C9 -33.3(4) . . . . ?
C1 N1 S1 O2 -36.1(4) . . . . ?
N2 N1 S1 O2 127.0(3) . . . . ?
C1 N1 S1 O3 96.0(3) . . . . ?
N2 N1 S1 O3 -101.0(3) . . . . ?
C1 N1 S1 C10 -152.6(3) . . . . ?
N2 N1 S1 C10 10.5(3) . . . . ?
N2 N1 C1 O1 -176.4(4) . . . . ?
S1 N1 C1 O1 -15.0(5) . . . . ?
N2 N1 C1 C2 5.1(5) . . . . ?
S1 N1 C1 C2 166.6(3) . . . . ?
O1 C1 C2 C3 -5.3(6) . . . . ?
N1 C1 C2 C3 173.1(4) . . . . ?
C1 C2 C3 C4 -78.2(6) . . . . ?
C1 C2 C3 C8 102.1(5) . . . . ?
C8 C3 C4 C5 -0.6(8) . . . . ?
C2 C3 C4 C5 179.7(5) . . . . ?
C3 C4 C5 C6 -0.2(9) . . . . ?
C4 C5 C6 C7 0.9(11) . . . . ?
C5 C6 C7 C8 -0.8(11) . . . . ?
C6 C7 C8 C3 -0.1(10) . . . . ?
C4 C3 C8 C7 0.7(8) . . . . ?
C2 C3 C8 C7 -179.6(5) . . . . ?
N1 N2 C9 C10 44.3(4) . . . . ?
N2 C9 C10 C11 -157.7(4) . . . . ?
N2 C9 C10 S1 -35.4(4) . . . . ?
O2 S1 C10 C11 25.9(4) . . . . ?
O3 S1 C10 C11 -107.2(3) . . . . ?
N1 S1 C10 C11 140.5(3) . . . . ?
O2 S1 C10 C9 -100.3(3) . . . . ?
O3 S1 C10 C9 126.6(3) . . . . ?
N1 S1 C10 C9 14.3(3) . . . . ?
C9 C10 C11 C12 -64.0(5) . . . . ?
S1 C10 C11 C12 178.2(3) . . . . ?
C10 C11 C12 S2 -88.2(4) . . . . ?
O4 S2 C12 C11 176.6(3) . . . . ?
O5 S2 C12 C11 40.1(4) . . . . ?
F1 S2 C12 C11 -71.2(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.488
_refine_diff_density_min         -0.426
_refine_diff_density_rms         0.066
