# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2021

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

data_20210329a
_database_code_depnum_ccdc_archive 'CCDC 2080867'
loop_
_audit_author_name
_audit_author_address
'Wen Wan'
;Shanghai University
China
;
_audit_update_record             
;
2021-04-29 deposited with the CCDC.	2021-07-22 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H11 F2 N O S2'
_chemical_formula_iupac          ?
_chemical_formula_weight         323.37
_chemical_absolute_configuration ad

_chemical_melting_point          ?

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   5.89830(10)
_cell_length_b                   15.4491(2)
_cell_length_c                   15.8136(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1440.99(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9648
_cell_measurement_theta_min      2.79
_cell_measurement_theta_max      66.67
_cell_measurement_temperature    303.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.070
_exptl_crystal_density_diffrn    1.491
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             664

_exptl_absorpt_coefficient_mu    3.544
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
;
_exptl_absorpt_correction_T_min  0.5569
_exptl_absorpt_correction_T_max  0.7528

_exptl_special_details           
;
;

_diffrn_ambient_temperature      303.(2)

_diffrn_source                   ?
_diffrn_source_type              ?
_diffrn_source_power             ?
_diffrn_source_current           ?
_diffrn_source_voltage           ?

_diffrn_radiation_probe          ?
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device       'Bruker APEX-II CCD'
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            11956
_diffrn_reflns_av_R_equivalents  0.0250
_diffrn_reflns_av_unetI/netI     0.0233
_diffrn_reflns_theta_min         4.00
_diffrn_reflns_theta_max         66.66
_diffrn_reflns_theta_full        66.66
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18

_refine_special_details          
;
;

_reflns_number_total             2520
_reflns_number_gt                2498
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.694
_reflns_Friedel_fraction_max     0.992
_reflns_Friedel_fraction_full    0.993

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0292
_refine_ls_R_factor_gt           0.0291
_refine_ls_wR_factor_gt          0.0902
_refine_ls_wR_factor_ref         0.0904
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.065
_refine_ls_number_reflns         2520
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0642P)²+0.1684P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.291
_refine_diff_density_min         -0.214
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;

Flack x determined using 1011 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.087(5)

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1 0.22541(13) 0.39958(5) 0.60369(5) 0.0557(2) Uani d . . . 1 . .
S S2 0.51159(16) 0.53525(4) 0.69071(4) 0.0558(2) Uani d . . . 1 . .
F F1 0.4933(7) 0.57035(14) 0.53025(13) 0.1092(12) Uani d . . . 1 . .
F F2 0.8234(5) 0.53933(14) 0.5755(2) 0.1097(11) Uani d . . . 1 . .
O O1 0.7862(4) 0.93734(12) 0.65407(14) 0.0560(5) Uani d . . . 1 . .
N N1 0.6095(4) 0.36497(15) 0.67659(14) 0.0466(5) Uani d . . . 1 . .
C C1 0.3144(5) 0.29359(17) 0.60431(17) 0.0437(6) Uani d . . . 1 . .
C C2 0.2120(6) 0.22087(19) 0.56784(18) 0.0533(7) Uani d . . . 1 . .
H H2 0.071992 0.224908 0.541066 0.064 Uiso calc U . R 1 . .
C C3 0.3252(7) 0.14333(19) 0.57291(19) 0.0588(8) Uani d . . . 1 . .
H H3 0.261452 0.09442 0.548222 0.071 Uiso calc U . R 1 . .
C C4 0.5319(7) 0.13616(19) 0.61387(19) 0.0615(9) Uani d . . . 1 . .
H H4 0.603724 0.082647 0.616611 0.074 Uiso calc U . R 1 . .
C C5 0.6326(6) 0.2075(2) 0.6507(2) 0.0549(7) Uani d . . . 1 . .
H H5 0.770853 0.202393 0.678491 0.066 Uiso calc U . R 1 . .
C C6 0.5233(5) 0.28719(16) 0.64539(15) 0.0427(6) Uani d . . . 1 . .
C C7 0.4710(5) 0.42703(17) 0.65791(16) 0.0450(6) Uani d . . . 1 . .
C C8 0.6313(7) 0.5830(2) 0.5964(2) 0.0587(8) Uani d . . . 1 . .
C C9 0.6775(6) 0.67685(18) 0.61144(17) 0.0496(7) Uani d . . . 1 . .
C C10 0.5229(6) 0.7391(2) 0.5856(2) 0.0569(7) Uani d . . . 1 . .
H H10 0.390471 0.722512 0.558105 0.068 Uiso calc U . R 1 . .
C C11 0.5654(5) 0.8252(2) 0.6006(2) 0.0561(7) Uani d . . . 1 . .
H H11 0.46157 0.866774 0.583053 0.067 Uiso calc U . R 1 . .
C C12 0.7616(5) 0.85041(16) 0.64178(17) 0.0439(6) Uani d . . . 1 . .
C C13 0.9169(6) 0.78899(19) 0.6680(2) 0.0542(7) Uani d . . . 1 . .
H H13 1.048954 0.805596 0.695711 0.065 Uiso calc U . R 1 . .
C C14 0.8731(6) 0.70226(19) 0.6523(2) 0.0584(8) Uani d . . . 1 . .
H H14 0.97714 0.660628 0.669537 0.07 Uiso calc U . R 1 . .
C C15 1.0005(6) 0.96793(19) 0.6846(2) 0.0616(8) Uani d . . . 1 . .
H H15A 1.118074 0.950975 0.646056 0.092 Uiso calc U . R 1 . .
H H15B 1.029971 0.943396 0.739292 0.092 Uiso calc U . R 1 . .
H H15C 0.996859 1.029891 0.688947 0.092 Uiso calc U . R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C1 . 1.719(3) ?
S1 C7 . 1.736(3) ?
S2 C7 . 1.767(3) ?
S2 C8 . 1.808(3) ?
F1 C8 . 1.339(4) ?
F2 C8 . 1.359(5) ?
O1 C12 . 1.365(3) ?
O1 C15 . 1.433(4) ?
N1 C7 . 1.294(4) ?
N1 C6 . 1.395(3) ?
C1 C6 . 1.396(4) ?
C1 C2 . 1.400(4) ?
C2 C3 . 1.374(5) ?
C2 H2 . 0.93 ?
C3 C4 . 1.385(5) ?
C3 H3 . 0.93 ?
C4 C5 . 1.380(5) ?
C4 H4 . 0.93 ?
C5 C6 . 1.392(4) ?
C5 H5 . 0.93 ?
C8 C9 . 1.494(4) ?
C9 C14 . 1.379(5) ?
C9 C10 . 1.386(4) ?
C10 C11 . 1.375(4) ?
C10 H10 . 0.93 ?
C11 C12 . 1.384(4) ?
C11 H11 . 0.93 ?
C12 C13 . 1.382(4) ?
C13 C14 . 1.387(4) ?
C13 H13 . 0.93 ?
C14 H14 . 0.93 ?
C15 H15A . 0.96 ?
C15 H15B . 0.96 ?
C15 H15C . 0.96 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 S1 C7 . . 88.58(13) ?
C7 S2 C8 . . 101.36(13) ?
C12 O1 C15 . . 117.8(2) ?
C7 N1 C6 . . 109.1(2) ?
C6 C1 C2 . . 121.0(3) ?
C6 C1 S1 . . 109.8(2) ?
C2 C1 S1 . . 129.1(2) ?
C3 C2 C1 . . 117.8(3) ?
C3 C2 H2 . . 121.1 ?
C1 C2 H2 . . 121.1 ?
C2 C3 C4 . . 121.7(3) ?
C2 C3 H3 . . 119.2 ?
C4 C3 H3 . . 119.2 ?
C5 C4 C3 . . 120.8(3) ?
C5 C4 H4 . . 119.6 ?
C3 C4 H4 . . 119.6 ?
C4 C5 C6 . . 118.8(3) ?
C4 C5 H5 . . 120.6 ?
C6 C5 H5 . . 120.6 ?
C5 C6 N1 . . 124.9(3) ?
C5 C6 C1 . . 119.9(2) ?
N1 C6 C1 . . 115.2(2) ?
N1 C7 S1 . . 117.3(2) ?
N1 C7 S2 . . 123.3(2) ?
S1 C7 S2 . . 119.29(16) ?
F1 C8 F2 . . 104.2(3) ?
F1 C8 C9 . . 112.2(3) ?
F2 C8 C9 . . 111.6(3) ?
F1 C8 S2 . . 110.3(3) ?
F2 C8 S2 . . 108.8(2) ?
C9 C8 S2 . . 109.6(2) ?
C14 C9 C10 . . 119.4(3) ?
C14 C9 C8 . . 120.2(3) ?
C10 C9 C8 . . 120.4(3) ?
C11 C10 C9 . . 120.0(3) ?
C11 C10 H10 . . 120.0 ?
C9 C10 H10 . . 120.0 ?
C10 C11 C12 . . 120.4(3) ?
C10 C11 H11 . . 119.8 ?
C12 C11 H11 . . 119.8 ?
O1 C12 C13 . . 124.2(3) ?
O1 C12 C11 . . 115.7(2) ?
C13 C12 C11 . . 120.1(3) ?
C12 C13 C14 . . 119.1(3) ?
C12 C13 H13 . . 120.5 ?
C14 C13 H13 . . 120.5 ?
C9 C14 C13 . . 121.0(3) ?
C9 C14 H14 . . 119.5 ?
C13 C14 H14 . . 119.5 ?
O1 C15 H15A . . 109.5 ?
O1 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
O1 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C7 S1 C1 C6 . . . . -0.1(2) ?
C7 S1 C1 C2 . . . . -177.2(3) ?
C6 C1 C2 C3 . . . . -0.8(4) ?
S1 C1 C2 C3 . . . . 176.1(2) ?
C1 C2 C3 C4 . . . . 1.1(5) ?
C2 C3 C4 C5 . . . . -0.5(5) ?
C3 C4 C5 C6 . . . . -0.5(5) ?
C4 C5 C6 N1 . . . . -177.3(3) ?
C4 C5 C6 C1 . . . . 0.8(4) ?
C7 N1 C6 C5 . . . . 177.1(3) ?
C7 N1 C6 C1 . . . . -1.1(3) ?
C2 C1 C6 C5 . . . . -0.1(4) ?
S1 C1 C6 C5 . . . . -177.6(2) ?
C2 C1 C6 N1 . . . . 178.1(2) ?
S1 C1 C6 N1 . . . . 0.7(3) ?
C6 N1 C7 S1 . . . . 1.0(3) ?
C6 N1 C7 S2 . . . . 176.78(19) ?
C1 S1 C7 N1 . . . . -0.6(2) ?
C1 S1 C7 S2 . . . . -176.51(17) ?
C8 S2 C7 N1 . . . . 99.6(3) ?
C8 S2 C7 S1 . . . . -84.7(2) ?
C7 S2 C8 F1 . . . . 55.7(3) ?
C7 S2 C8 F2 . . . . -58.0(3) ?
C7 S2 C8 C9 . . . . 179.7(2) ?
F1 C8 C9 C14 . . . . -155.0(3) ?
F2 C8 C9 C14 . . . . -38.5(4) ?
S2 C8 C9 C14 . . . . 82.1(3) ?
F1 C8 C9 C10 . . . . 25.8(4) ?
F2 C8 C9 C10 . . . . 142.3(3) ?
S2 C8 C9 C10 . . . . -97.1(3) ?
C14 C9 C10 C11 . . . . 0.1(5) ?
C8 C9 C10 C11 . . . . 179.2(3) ?
C9 C10 C11 C12 . . . . -0.2(5) ?
C15 O1 C12 C13 . . . . 9.6(4) ?
C15 O1 C12 C11 . . . . -170.8(3) ?
C10 C11 C12 O1 . . . . -179.5(3) ?
C10 C11 C12 C13 . . . . 0.1(5) ?
O1 C12 C13 C14 . . . . 179.7(3) ?
C11 C12 C13 C14 . . . . 0.1(5) ?
C10 C9 C14 C13 . . . . 0.1(5) ?
C8 C9 C14 C13 . . . . -179.0(3) ?
C12 C13 C14 C9 . . . . -0.2(5) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C15 H15B S1 3_656 0.96 2.98 3.755(4) 138.4 ?

