# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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. 
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data_SGK-07-F
_database_code_depnum_ccdc_archive 'CCDC 1540070'
_audit_update_record             
;
2017-03-24 deposited with the CCDC.
2017-07-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H13 F N2 O3 S'
_chemical_formula_sum            'C16 H13 F N2 O3 S'
_chemical_formula_weight         332.34

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

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

_cell_length_a                   8.6807(3)
_cell_length_b                   10.7996(3)
_cell_length_c                   15.8435(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1485.30(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    9196
_cell_measurement_theta_min      2.57
_cell_measurement_theta_max      28.30

_exptl_crystal_description       Block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.486
_exptl_crystal_F_000             688
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.246
_shelx_estimated_absorpt_T_min   0.950
_shelx_estimated_absorpt_T_max   0.971
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.7159
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      223(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'PHOTON 100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            48956
_diffrn_reflns_av_unetI/netI     0.0180
_diffrn_reflns_av_R_equivalents  0.0466
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.282
_diffrn_reflns_theta_max         28.368
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3730
_reflns_number_gt                3294
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.745
_reflns_Friedel_fraction_max     0.997
_reflns_Friedel_fraction_full    1.000

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0400P)²+0.3615P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1296 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.379(15)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3730
_refine_ls_number_parameters     209
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0423
_refine_ls_R_factor_gt           0.0334
_refine_ls_wR_factor_ref         0.0849
_refine_ls_wR_factor_gt          0.0805
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_restrained_S_all      1.092
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.7718(3) 0.47592(17) -0.02516(14) 0.0364(5) Uani 1 1 d . . . . .
C1 C 0.7861(3) 0.3877(2) 0.03657(16) 0.0359(5) Uani 1 1 d . . . . .
H1 H 0.7617 0.3997 0.0938 0.043 Uiso 1 1 calc R U . . .
C2 C 0.8410(3) 0.2796(2) 0.00286(16) 0.0314(5) Uani 1 1 d . . . . .
C3 C 0.8638(3) 0.3018(2) -0.08560(16) 0.0306(5) Uani 1 1 d . . . . .
C4 C 0.9179(3) 0.2305(2) -0.15282(16) 0.0363(6) Uani 1 1 d . . . . .
H4 H 0.9468 0.1476 -0.1443 0.044 Uiso 1 1 calc R U . . .
C5 C 0.9283(4) 0.2828(3) -0.23159(18) 0.0448(7) Uani 1 1 d . . . . .
H5 H 0.9651 0.2364 -0.2776 0.054 Uiso 1 1 calc R U . . .
C6 C 0.8835(4) 0.4055(3) -0.24241(18) 0.0476(7) Uani 1 1 d . . . . .
C7 C 0.8277(3) 0.4801(2) -0.18007(18) 0.0433(6) Uani 1 1 d . . . . .
H7 H 0.7973 0.5623 -0.1902 0.052 Uiso 1 1 calc R U . . .
C8 C 0.8189(3) 0.4260(2) -0.10032(16) 0.0337(5) Uani 1 1 d . . . . .
C9 C 0.7312(3) 0.6056(2) -0.0118(2) 0.0456(7) Uani 1 1 d . . . . .
H9A H 0.8237 0.6558 -0.0131 0.068 Uiso 1 1 calc R U . . .
H9B H 0.6812 0.6146 0.0426 0.068 Uiso 1 1 calc R U . . .
H9C H 0.6615 0.6325 -0.0560 0.068 Uiso 1 1 calc R U . . .
F1 F 0.8984(3) 0.45404(18) -0.32137(11) 0.0740(6) Uani 1 1 d . . . . .
C10 C 0.8613(3) 0.1566(2) 0.04509(14) 0.0294(5) Uani 1 1 d . . . . .
H10 H 0.9555 0.1185 0.0213 0.035 Uiso 1 1 calc R U . . .
C11 C 0.8806(3) 0.1597(2) 0.14012(16) 0.0304(5) Uani 1 1 d . . . . .
C12 C 0.9791(3) 0.2452(2) 0.17815(18) 0.0410(6) Uani 1 1 d . . . . .
H12 H 1.0308 0.3032 0.1442 0.049 Uiso 1 1 calc R U . . .
C13 C 1.0023(4) 0.2468(3) 0.26392(19) 0.0494(7) Uani 1 1 d . . . . .
H13 H 1.0690 0.3057 0.2879 0.059 Uiso 1 1 calc R U . . .
C14 C 0.9274(4) 0.1617(3) 0.31535(19) 0.0501(7) Uani 1 1 d . . . . .
H14 H 0.9422 0.1635 0.3741 0.060 Uiso 1 1 calc R U . . .
C15 C 0.8319(4) 0.0752(3) 0.27985(17) 0.0442(6) Uani 1 1 d . . . . .
H15 H 0.7810 0.0169 0.3140 0.053 Uiso 1 1 calc R U . . .
C16 C 0.8111(3) 0.0745(2) 0.19326(16) 0.0330(5) Uani 1 1 d . . . . .
O1 O 0.7107(2) -0.01874(15) 0.16340(11) 0.0391(4) Uani 1 1 d . . . . .
S1 S 0.72484(7) -0.05532(5) 0.06639(4) 0.03200(15) Uani 1 1 d . . . . .
O2 O 0.8699(2) -0.11190(16) 0.05406(13) 0.0447(5) Uani 1 1 d . . . . .
O3 O 0.5875(2) -0.11936(17) 0.04792(13) 0.0451(5) Uani 1 1 d . . . . .
N2 N 0.7273(3) 0.07722(16) 0.01872(13) 0.0332(4) Uani 1 1 d . . . . .
H2 H 0.6392 0.1177 0.0304 0.040 Uiso 1 1 d 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
N1 C8 1.370(3) . ?
N1 C1 1.371(3) . ?
N1 C9 1.459(3) . ?
C1 C2 1.369(3) . ?
C1 H1 0.9400 . ?
C2 C3 1.436(4) . ?
C2 C10 1.498(3) . ?
C3 C4 1.396(3) . ?
C3 C8 1.415(3) . ?
C4 C5 1.373(4) . ?
C4 H4 0.9400 . ?
C5 C6 1.392(4) . ?
C5 H5 0.9400 . ?
C6 F1 1.362(3) . ?
C6 C7 1.363(4) . ?
C7 C8 1.394(4) . ?
C7 H7 0.9400 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 H9C 0.9700 . ?
C10 N2 1.504(3) . ?
C10 C11 1.515(3) . ?
C10 H10 0.9900 . ?
C11 C16 1.386(3) . ?
C11 C12 1.395(3) . ?
C12 C13 1.374(4) . ?
C12 H12 0.9400 . ?
C13 C14 1.390(4) . ?
C13 H13 0.9400 . ?
C14 C15 1.370(4) . ?
C14 H14 0.9400 . ?
C15 C16 1.384(3) . ?
C15 H15 0.9400 . ?
C16 O1 1.413(3) . ?
O1 S1 1.5916(19) . ?
S1 O3 1.4088(19) . ?
S1 O2 1.4136(18) . ?
S1 N2 1.6186(19) . ?
N2 H2 0.9000 . ?

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
C8 N1 C1 108.62(19) . . ?
C8 N1 C9 125.2(2) . . ?
C1 N1 C9 125.8(2) . . ?
C2 C1 N1 110.2(2) . . ?
C2 C1 H1 124.9 . . ?
N1 C1 H1 124.9 . . ?
C1 C2 C3 106.7(2) . . ?
C1 C2 C10 128.5(2) . . ?
C3 C2 C10 124.6(2) . . ?
C4 C3 C8 119.3(2) . . ?
C4 C3 C2 134.4(2) . . ?
C8 C3 C2 106.3(2) . . ?
C5 C4 C3 119.3(2) . . ?
C5 C4 H4 120.4 . . ?
C3 C4 H4 120.4 . . ?
C4 C5 C6 119.0(3) . . ?
C4 C5 H5 120.5 . . ?
C6 C5 H5 120.5 . . ?
F1 C6 C7 118.1(3) . . ?
F1 C6 C5 116.9(3) . . ?
C7 C6 C5 124.9(3) . . ?
C6 C7 C8 115.4(2) . . ?
C6 C7 H7 122.3 . . ?
C8 C7 H7 122.3 . . ?
N1 C8 C7 129.7(2) . . ?
N1 C8 C3 108.2(2) . . ?
C7 C8 C3 122.1(2) . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C2 C10 N2 106.88(18) . . ?
C2 C10 C11 115.9(2) . . ?
N2 C10 C11 111.98(18) . . ?
C2 C10 H10 107.2 . . ?
N2 C10 H10 107.2 . . ?
C11 C10 H10 107.2 . . ?
C16 C11 C12 116.4(2) . . ?
C16 C11 C10 122.7(2) . . ?
C12 C11 C10 120.8(2) . . ?
C13 C12 C11 121.7(3) . . ?
C13 C12 H12 119.1 . . ?
C11 C12 H12 119.1 . . ?
C12 C13 C14 120.2(3) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C15 C14 C13 119.6(3) . . ?
C15 C14 H14 120.2 . . ?
C13 C14 H14 120.2 . . ?
C14 C15 C16 119.3(3) . . ?
C14 C15 H15 120.3 . . ?
C16 C15 H15 120.3 . . ?
C15 C16 C11 122.8(2) . . ?
C15 C16 O1 114.6(2) . . ?
C11 C16 O1 122.6(2) . . ?
C16 O1 S1 116.93(15) . . ?
O3 S1 O2 120.87(10) . . ?
O3 S1 O1 104.92(11) . . ?
O2 S1 O1 108.02(12) . . ?
O3 S1 N2 110.38(12) . . ?
O2 S1 N2 107.83(11) . . ?
O1 S1 N2 103.42(10) . . ?
C10 N2 S1 112.60(15) . . ?
C10 N2 H2 108.9 . . ?
S1 N2 H2 108.9 . . ?

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
C8 N1 C1 C2 -0.5(3) . . . . ?
C9 N1 C1 C2 -173.7(2) . . . . ?
N1 C1 C2 C3 0.5(3) . . . . ?
N1 C1 C2 C10 -174.2(2) . . . . ?
C1 C2 C3 C4 179.2(3) . . . . ?
C10 C2 C3 C4 -5.9(4) . . . . ?
C1 C2 C3 C8 -0.3(3) . . . . ?
C10 C2 C3 C8 174.6(2) . . . . ?
C8 C3 C4 C5 0.9(4) . . . . ?
C2 C3 C4 C5 -178.6(3) . . . . ?
C3 C4 C5 C6 -0.5(4) . . . . ?
C4 C5 C6 F1 178.9(3) . . . . ?
C4 C5 C6 C7 -0.5(5) . . . . ?
F1 C6 C7 C8 -178.5(2) . . . . ?
C5 C6 C7 C8 1.0(5) . . . . ?
C1 N1 C8 C7 -178.8(3) . . . . ?
C9 N1 C8 C7 -5.5(4) . . . . ?
C1 N1 C8 C3 0.3(3) . . . . ?
C9 N1 C8 C3 173.6(2) . . . . ?
C6 C7 C8 N1 178.5(3) . . . . ?
C6 C7 C8 C3 -0.5(4) . . . . ?
C4 C3 C8 N1 -179.5(2) . . . . ?
C2 C3 C8 N1 0.0(3) . . . . ?
C4 C3 C8 C7 -0.4(4) . . . . ?
C2 C3 C8 C7 179.2(2) . . . . ?
C1 C2 C10 N2 101.1(3) . . . . ?
C3 C2 C10 N2 -72.7(3) . . . . ?
C1 C2 C10 C11 -24.5(4) . . . . ?
C3 C2 C10 C11 161.7(2) . . . . ?
C2 C10 C11 C16 139.2(2) . . . . ?
N2 C10 C11 C16 16.2(3) . . . . ?
C2 C10 C11 C12 -45.1(3) . . . . ?
N2 C10 C11 C12 -168.0(2) . . . . ?
C16 C11 C12 C13 -1.7(4) . . . . ?
C10 C11 C12 C13 -177.7(3) . . . . ?
C11 C12 C13 C14 0.2(5) . . . . ?
C12 C13 C14 C15 0.8(5) . . . . ?
C13 C14 C15 C16 -0.3(4) . . . . ?
C14 C15 C16 C11 -1.4(4) . . . . ?
C14 C15 C16 O1 179.8(2) . . . . ?
C12 C11 C16 C15 2.3(4) . . . . ?
C10 C11 C16 C15 178.2(2) . . . . ?
C12 C11 C16 O1 -178.9(2) . . . . ?
C10 C11 C16 O1 -3.0(4) . . . . ?
C15 C16 O1 S1 -159.68(19) . . . . ?
C11 C16 O1 S1 21.5(3) . . . . ?
C16 O1 S1 O3 -163.12(16) . . . . ?
C16 O1 S1 O2 66.71(18) . . . . ?
C16 O1 S1 N2 -47.40(19) . . . . ?
C2 C10 N2 S1 -174.71(16) . . . . ?
C11 C10 N2 S1 -46.8(2) . . . . ?
O3 S1 N2 C10 172.48(16) . . . . ?
O2 S1 N2 C10 -53.54(19) . . . . ?
O1 S1 N2 C10 60.71(18) . . . . ?

_refine_diff_density_max         0.262
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.042

