# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_fg748m
_database_code_depnum_ccdc_archive 'CCDC 1831294'
loop_
_audit_author_name
_audit_author_address
'Rakesh Ganguly'
;Nanyang Technological University
Singapore
;
_audit_update_record             
;
2018-03-21 deposited with the CCDC.	2020-10-30 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H13 N O S'
_chemical_formula_iupac          ?
_chemical_formula_weight         195.27

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_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                   8.0113(3)
_cell_length_b                   9.6951(3)
_cell_length_c                   13.9342(4)
_cell_angle_alpha                90
_cell_angle_beta                 106.6239(13)
_cell_angle_gamma                90
_cell_volume                     1037.04(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    310
_cell_measurement_theta_min      2.6475
_cell_measurement_theta_max      28.5696
_cell_measurement_temperature    138.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            'light yellow'
_exptl_crystal_size_max          0.497
_exptl_crystal_size_mid          0.378
_exptl_crystal_size_min          0.276
_exptl_crystal_density_diffrn    1.251
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             416

_exptl_absorpt_coefficient_mu    0.273
_exptl_absorpt_correction_type   'Numerical Mu Calculated'
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.64
_exptl_absorpt_correction_T_max  0.75

_exptl_special_details           
;
;

_diffrn_ambient_temperature      138.(2)

_diffrn_source                   'Incoatec microfocus source'
_diffrn_source_type              'Bruker D8 Quest'

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'Multilayer Mirror'

_diffrn_measurement_device_type  'Photon II CPADs detector'
_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 7.4074

_diffrn_reflns_number            14471
_diffrn_reflns_av_R_equivalents  0.0560
_diffrn_reflns_av_unetI/netI     0.0498
_diffrn_reflns_theta_min         2.60
_diffrn_reflns_theta_max         31.05
_diffrn_reflns_theta_full        31.05
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.992
_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       -20
_diffrn_reflns_limit_l_max       20

_refine_special_details          
;
;

_reflns_number_total             3299
_reflns_number_gt                2591
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0645
_refine_ls_R_factor_gt           0.0453
_refine_ls_wR_factor_gt          0.0975
_refine_ls_wR_factor_ref         0.1085
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_refine_ls_number_reflns         3299
_refine_ls_number_parameters     121
_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)+(0.0338P)²+0.4866P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.013
_refine_ls_shift/su_mean         0.001
_refine_diff_density_max         0.337
_refine_diff_density_min         -0.225
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'APEX3 (Bruker AXS Inc., 2017)'
_computing_cell_refinement       'APEX3 v2017.3-0 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'XS, VERSION 2013/1'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  'APEX3 (Bruker AXS Inc., 2017)'

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
C C1 0.33781(18) 0.62565(14) 0.37433(10) 0.0223(3) Uani d . . . 1 . .
C C2 0.48747(19) 0.69931(16) 0.37906(11) 0.0277(3) Uani d . . . 1 . .
H H2 0.542947 0.752134 0.436801 0.033 Uiso calc U . R 1 . .
C C3 0.55524(19) 0.69485(15) 0.29825(12) 0.0273(3) Uani d . . . 1 . .
H H3 0.658715 0.744672 0.301231 0.033 Uiso calc U . R 1 . .
C C4 0.47533(19) 0.61916(14) 0.21291(10) 0.0226(3) Uani d . . . 1 . .
C C5 0.5515(2) 0.6129(2) 0.12619(13) 0.0373(4) Uani d . . . 1 . .
H H5A 0.605995 0.701557 0.119658 0.056 Uiso calc U . R 1 . .
H H5B 0.45891 0.593376 0.064499 0.056 Uiso calc U . R 1 . .
H H5C 0.639372 0.53965 0.137875 0.056 Uiso calc U . R 1 . .
C C6 0.3242(2) 0.54735(15) 0.21059(11) 0.0262(3) Uani d . . . 1 . .
H H6 0.266637 0.496109 0.152424 0.031 Uiso calc U . R 1 . .
C C7 0.25553(19) 0.54884(15) 0.29145(11) 0.0253(3) Uani d . . . 1 . .
H H7 0.153484 0.497672 0.289506 0.03 Uiso calc U . R 1 . .
C C8 0.14830(17) 0.70875(14) 0.46572(10) 0.0205(3) Uani d . . . 1 . .
C C9 0.1960(2) 0.58732(16) 0.62548(11) 0.0289(3) Uani d . . . 1 . .
H H9A 0.132168 0.499888 0.611668 0.043 Uiso calc U . R 1 . .
H H9B 0.198826 0.619735 0.69255 0.043 Uiso calc U . R 1 . .
H H9C 0.315283 0.573508 0.622041 0.043 Uiso calc U . R 1 . .
C C10 -0.0369(2) 0.76389(18) 0.57069(12) 0.0318(3) Uani d . . . 1 . .
H H10A -0.040874 0.858272 0.544963 0.048 Uiso calc U . R 1 . .
H H10B -0.021643 0.766523 0.643011 0.048 Uiso calc U . R 1 . .
H H10C -0.146101 0.716444 0.537245 0.048 Uiso calc U . R 1 . .
N N1 0.10875(15) 0.69004(12) 0.55113(9) 0.0225(2) Uani d . . . 1 . .
O O1 0.27668(14) 0.62060(11) 0.45933(7) 0.0286(2) Uani d . . . 1 . .
S S1 0.05694(5) 0.82277(4) 0.37714(3) 0.02967(12) Uani d . . . 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
C1 C7 . 1.374(2) ?
C1 C2 . 1.381(2) ?
C1 O1 . 1.4060(16) ?
C2 C3 . 1.384(2) ?
C3 C4 . 1.388(2) ?
C4 C6 . 1.389(2) ?
C4 C5 . 1.503(2) ?
C6 C7 . 1.388(2) ?
C8 N1 . 1.3287(17) ?
C8 O1 . 1.3596(16) ?
C8 S1 . 1.6626(14) ?
C9 N1 . 1.4625(18) ?
C10 N1 . 1.4599(18) ?

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
C7 C1 C2 . . 121.45(13) ?
C7 C1 O1 . . 119.36(13) ?
C2 C1 O1 . . 118.99(13) ?
C1 C2 C3 . . 118.85(13) ?
C2 C3 C4 . . 121.43(13) ?
C3 C4 C6 . . 118.06(13) ?
C3 C4 C5 . . 121.08(14) ?
C6 C4 C5 . . 120.85(14) ?
C7 C6 C4 . . 121.40(13) ?
C1 C7 C6 . . 118.79(13) ?
N1 C8 O1 . . 110.58(12) ?
N1 C8 S1 . . 126.05(11) ?
O1 C8 S1 . . 123.37(10) ?
C8 N1 C10 . . 120.57(12) ?
C8 N1 C9 . . 122.65(12) ?
C10 N1 C9 . . 116.55(12) ?
C8 O1 C1 . . 119.05(11) ?

####################################################################### 
# 
# 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_fg754m
_database_code_depnum_ccdc_archive 'CCDC 1831296'
loop_
_audit_author_name
_audit_author_address
'Rakesh Ganguly'
;Nanyang Technological University
Singapore
;
_audit_update_record             
;
2018-03-21 deposited with the CCDC.	2020-10-30 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H6 F5 N O S'
_chemical_formula_iupac          ?
_chemical_formula_weight         271.21

_chemical_melting_point          ?

_space_group_crystal_system      triclinic
_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                   6.358(2)
_cell_length_b                   7.684(3)
_cell_length_c                   11.573(4)
_cell_angle_alpha                91.215(13)
_cell_angle_beta                 104.219(11)
_cell_angle_gamma                94.232(12)
_cell_volume                     546.1(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7101
_cell_measurement_theta_min      3.3638
_cell_measurement_theta_max      29.6158
_cell_measurement_temperature    301.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.360
_exptl_crystal_size_min          0.280
_exptl_crystal_density_diffrn    1.649
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             272

_exptl_absorpt_coefficient_mu    0.347
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.73
_exptl_absorpt_correction_T_max  0.91

_exptl_special_details           
;
;

_diffrn_ambient_temperature      301.(2)

_diffrn_source                   'Incoatec microfocus source'
_diffrn_source_type              'Bruker D8 Quest'

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'Multilayer Mirror'

_diffrn_measurement_device_type  'Photon II CPADs detector'
_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 7.4074

_diffrn_reflns_number            18881
_diffrn_reflns_av_R_equivalents  0.0625
_diffrn_reflns_av_unetI/netI     0.0416
_diffrn_reflns_theta_min         2.66
_diffrn_reflns_theta_max         29.69
_diffrn_reflns_theta_full        29.69
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measured_fraction_theta_full 0.979
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16

_refine_special_details          
;
;

_reflns_number_total             3036
_reflns_number_gt                1976
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0930
_refine_ls_R_factor_gt           0.0594
_refine_ls_wR_factor_gt          0.1431
_refine_ls_wR_factor_ref         0.1678
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_refine_ls_number_reflns         3036
_refine_ls_number_parameters     156
_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)+(0.0664P)²+0.2503P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.245
_refine_diff_density_min         -0.255
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'APEX3 (Bruker AXS Inc., 2017)'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'XS, VERSION 2013/1'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  'APEX3 (Bruker AXS Inc., 2017)'

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
C C1 0.7456(3) 0.2432(3) 0.76802(19) 0.0508(5) Uani d . . . 1 . .
C C2 0.7511(4) 0.0980(3) 0.8353(2) 0.0532(5) Uani d . . . 1 . .
C C3 0.7458(4) 0.1125(3) 0.9536(2) 0.0567(6) Uani d . . . 1 . .
C C4 0.7359(4) 0.2726(4) 1.0041(2) 0.0590(6) Uani d . . . 1 . .
C C5 0.7305(4) 0.4193(3) 0.9380(2) 0.0576(6) Uani d . . . 1 . .
C C6 0.7345(4) 0.4036(3) 0.8200(2) 0.0543(6) Uani d . . . 1 . .
C C7 0.9226(3) 0.2438(3) 0.60981(19) 0.0480(5) Uani d . . . 1 . .
C C8 0.6545(5) 0.2188(6) 0.4166(3) 0.0924(11) Uani d . . . 1 . .
H H8A 0.55414 0.247981 0.462474 0.139 Uiso calc U . R 1 . .
H H8B 0.620016 0.100286 0.385946 0.139 Uiso calc U . R 1 . .
H H8C 0.643738 0.295676 0.351479 0.139 Uiso calc U . R 1 . .
C C9 1.0503(6) 0.2504(5) 0.4305(3) 0.0791(9) Uani d . . . 1 . .
H H9A 1.147515 0.161282 0.456707 0.119 Uiso calc U . R 1 . .
H H9B 1.129127 0.363146 0.447958 0.119 Uiso calc U . R 1 . .
H H9C 0.988836 0.235064 0.346142 0.119 Uiso calc U . R 1 . .
F F1 0.7627(3) -0.0595(2) 0.78732(18) 0.0862(6) Uani d . . . 1 . .
F F2 0.7515(3) -0.0292(3) 1.01839(18) 0.0923(6) Uani d . . . 1 . .
F F3 0.7310(3) 0.2867(3) 1.11887(14) 0.0970(6) Uani d . . . 1 . .
F F4 0.7214(3) 0.5762(2) 0.9876(2) 0.0932(6) Uani d . . . 1 . .
F F5 0.7267(3) 0.5459(2) 0.75541(19) 0.0896(6) Uani d . . . 1 . .
N N1 0.8761(3) 0.2376(3) 0.49262(17) 0.0564(5) Uani d . . . 1 . .
O O1 0.7317(3) 0.2265(3) 0.64738(14) 0.0702(6) Uani d . . . 1 . .
S S1 1.16327(10) 0.26609(12) 0.70363(6) 0.0740(3) Uani d . . . 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
C1 C2 . 1.372(3) ?
C1 C6 . 1.374(4) ?
C1 O1 . 1.380(3) ?
C2 F1 . 1.335(3) ?
C2 C3 . 1.380(3) ?
C3 F2 . 1.333(3) ?
C3 C4 . 1.363(4) ?
C4 F3 . 1.339(3) ?
C4 C5 . 1.373(4) ?
C5 F4 . 1.335(3) ?
C5 C6 . 1.375(4) ?
C6 F5 . 1.335(3) ?
C7 N1 . 1.314(3) ?
C7 O1 . 1.384(3) ?
C7 S1 . 1.639(2) ?
C8 N1 . 1.461(4) ?
C9 N1 . 1.459(3) ?

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
C2 C1 C6 . . 119.1(2) ?
C2 C1 O1 . . 120.3(2) ?
C6 C1 O1 . . 120.3(2) ?
F1 C2 C1 . . 120.4(2) ?
F1 C2 C3 . . 119.0(2) ?
C1 C2 C3 . . 120.6(2) ?
F2 C3 C4 . . 120.2(2) ?
F2 C3 C2 . . 120.2(2) ?
C4 C3 C2 . . 119.7(2) ?
F3 C4 C3 . . 119.7(2) ?
F3 C4 C5 . . 119.9(3) ?
C3 C4 C5 . . 120.5(2) ?
F4 C5 C4 . . 120.4(2) ?
F4 C5 C6 . . 120.1(2) ?
C4 C5 C6 . . 119.5(2) ?
F5 C6 C1 . . 119.8(2) ?
F5 C6 C5 . . 119.5(2) ?
C1 C6 C5 . . 120.8(2) ?
N1 C7 O1 . . 109.53(19) ?
N1 C7 S1 . . 128.09(17) ?
O1 C7 S1 . . 122.38(16) ?
C7 N1 C9 . . 120.3(2) ?
C7 N1 C8 . . 123.8(2) ?
C9 N1 C8 . . 115.9(2) ?
C1 O1 C7 . . 118.28(17) ?

####################################################################### 
# 
# 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_fg780m
_database_code_depnum_ccdc_archive 'CCDC 1831295'
loop_
_audit_author_name
_audit_author_address
'Rakesh Ganguly'
;Nanyang Technological University
Singapore
;
_audit_update_record             
;
2018-03-21 deposited with the CCDC.	2020-10-30 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H10 N2 O3 S'
_chemical_formula_iupac          ?
_chemical_formula_weight         226.25
_chemical_absolute_configuration ?

_chemical_melting_point          ?

_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
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'

_cell_length_a                   7.0984(2)
_cell_length_b                   21.9932(6)
_cell_length_c                   6.5396(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1020.94(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5420
_cell_measurement_theta_min      3.0155
_cell_measurement_theta_max      30.9696
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.060
_exptl_crystal_density_diffrn    1.472
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             472

_exptl_absorpt_coefficient_mu    0.305
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.79
_exptl_absorpt_correction_T_max  0.98

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'Incoatec microfocus source'
_diffrn_source_type              'Bruker D8 Quest'

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'Multilayer Mirror'

_diffrn_measurement_device_type  'Photon II CPADs detector'
_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 7.4074

_diffrn_reflns_number            12424
_diffrn_reflns_av_R_equivalents  0.0488
_diffrn_reflns_av_unetI/netI     0.0416
_diffrn_reflns_theta_min         3.02
_diffrn_reflns_theta_max         31.09
_diffrn_reflns_theta_full        31.09
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       9

_refine_special_details          
;
;

_reflns_number_total             2677
_reflns_number_gt                2455
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0377
_refine_ls_R_factor_gt           0.0321
_refine_ls_wR_factor_gt          0.0752
_refine_ls_wR_factor_ref         0.0791
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.049
_refine_ls_number_reflns         2677
_refine_ls_number_parameters     138
_refine_ls_number_restraints     1
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0389P)²+0.1315P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.278
_refine_diff_density_min         -0.194
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;

Flack x determined using 751 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.07(5)

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'

_computing_data_collection       'APEX3 (Bruker AXS Inc., 2017)'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'XS, VERSION 2013/1'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  'APEX3 (Bruker AXS Inc., 2017)'

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
C C1 0.8841(2) 0.31934(9) -0.0550(4) 0.0170(4) Uani d . . . 1 . .
C C2 0.9552(2) 0.32540(8) -0.2505(4) 0.0166(4) Uani d . . . 1 . .
H H2 0.972556 0.364582 -0.308679 0.02 Uiso calc U . R 1 . .
C C3 1.0008(2) 0.27378(8) -0.3605(3) 0.0153(4) Uani d . . . 1 . .
H H3 1.049583 0.276806 -0.495364 0.018 Uiso calc U . R 1 . .
C C4 0.9739(2) 0.21766(8) -0.2698(3) 0.0141(4) Uani d . . . 1 . .
C C5 0.9065(3) 0.21112(9) -0.0719(4) 0.0170(4) Uani d . . . 1 . .
H H5 0.892171 0.171943 -0.012729 0.02 Uiso calc U . R 1 . .
C C6 0.8604(3) 0.26307(10) 0.0378(4) 0.0186(4) Uani d . . . 1 . .
H H6 0.813726 0.260194 0.173623 0.022 Uiso calc U . R 1 . .
C C7 0.9007(3) 0.40227(9) 0.1837(3) 0.0150(4) Uani d . . . 1 . .
C C8 0.6053(3) 0.46012(10) 0.1679(4) 0.0229(5) Uani d . . . 1 . .
H H8A 0.591042 0.441142 0.033156 0.034 Uiso calc U . R 1 . .
H H8B 0.584475 0.504027 0.156068 0.034 Uiso calc U . R 1 . .
H H8C 0.513005 0.442727 0.262681 0.034 Uiso calc U . R 1 . .
C C9 0.8588(3) 0.48904(11) 0.4090(4) 0.0295(5) Uani d . . . 1 . .
H H9A 0.798405 0.477015 0.537547 0.044 Uiso calc U . R 1 . .
H H9B 0.824087 0.531034 0.37598 0.044 Uiso calc U . R 1 . .
H H9C 0.995895 0.48609 0.423524 0.044 Uiso calc U . R 1 . .
N N1 0.7963(2) 0.44883(7) 0.2452(3) 0.0179(3) Uani d . . . 1 . .
N N2 1.0147(2) 0.16293(7) -0.3908(3) 0.0194(4) Uani d . . . 1 . .
O O1 0.8071(2) 0.37073(7) 0.0369(3) 0.0256(4) Uani d . . . 1 . .
O O2 0.9946(3) 0.11328(6) -0.3091(3) 0.0312(4) Uani d . . . 1 . .
O O3 1.0694(2) 0.16958(7) -0.5670(3) 0.0282(4) Uani d . . . 1 . .
S S1 1.11681(6) 0.38452(2) 0.26251(10) 0.01842(12) Uani d . . . 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
C1 C2 . 1.381(3) ?
C1 C6 . 1.389(3) ?
C1 O1 . 1.392(2) ?
C2 C3 . 1.382(3) ?
C3 C4 . 1.383(3) ?
C4 C5 . 1.387(3) ?
C4 N2 . 1.469(2) ?
C5 C6 . 1.388(3) ?
C7 N1 . 1.327(2) ?
C7 O1 . 1.358(3) ?
C7 S1 . 1.6645(19) ?
C8 N1 . 1.468(3) ?
C9 N1 . 1.458(3) ?
N2 O2 . 1.224(2) ?
N2 O3 . 1.224(3) ?

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
C2 C1 C6 . . 122.36(19) ?
C2 C1 O1 . . 117.71(19) ?
C6 C1 O1 . . 119.2(2) ?
C1 C2 C3 . . 119.21(18) ?
C2 C3 C4 . . 118.54(19) ?
C3 C4 C5 . . 122.70(18) ?
C3 C4 N2 . . 118.24(18) ?
C5 C4 N2 . . 119.05(17) ?
C4 C5 C6 . . 118.56(19) ?
C5 C6 C1 . . 118.6(2) ?
N1 C7 O1 . . 109.57(16) ?
N1 C7 S1 . . 127.04(16) ?
O1 C7 S1 . . 123.35(15) ?
C7 N1 C9 . . 121.37(17) ?
C7 N1 C8 . . 122.84(18) ?
C9 N1 C8 . . 115.57(17) ?
O2 N2 O3 . . 123.68(18) ?
O2 N2 C4 . . 118.19(19) ?
O3 N2 C4 . . 118.13(17) ?
C7 O1 C1 . . 121.87(15) ?

####################################################################### 
# 
# 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_fg790m
_database_code_depnum_ccdc_archive 'CCDC 1831298'
loop_
_audit_author_name
_audit_author_address
'Rakesh Ganguly'
;Nanyang Technological University
Singapore
;
_audit_update_record             
;
2018-03-21 deposited with the CCDC.	2020-10-30 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H17 N O4 S'
_chemical_formula_iupac          ?
_chemical_formula_weight         271.32

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_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                   37.1149(9)
_cell_length_b                   5.54430(10)
_cell_length_c                   12.8872(3)
_cell_angle_alpha                90
_cell_angle_beta                 95.9708(10)
_cell_angle_gamma                90
_cell_volume                     2637.49(10)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    7874
_cell_measurement_theta_min      3.3113
_cell_measurement_theta_max      30.5218
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.180
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1152

_exptl_absorpt_coefficient_mu    0.252
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.78
_exptl_absorpt_correction_T_max  0.96

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'Incoatec microfocus source'
_diffrn_source_type              'Bruker D8 Quest'

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'Multilayer Mirror'

_diffrn_measurement_device_type  'Photon II CPADs detector'
_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 7.4074

_diffrn_reflns_number            14769
_diffrn_reflns_av_R_equivalents  0.0296
_diffrn_reflns_av_unetI/netI     0.0281
_diffrn_reflns_theta_min         3.25
_diffrn_reflns_theta_max         30.61
_diffrn_reflns_theta_full        30.61
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.986
_diffrn_reflns_limit_h_min       -49
_diffrn_reflns_limit_h_max       52
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18

_refine_special_details          
;
;

_reflns_number_total             3992
_reflns_number_gt                3520
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0409
_refine_ls_R_factor_gt           0.0346
_refine_ls_wR_factor_gt          0.0904
_refine_ls_wR_factor_ref         0.0950
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_refine_ls_number_reflns         3992
_refine_ls_number_parameters     168
_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)+(0.0431P)²+2.0636P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.390
_refine_diff_density_min         -0.291
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'APEX3 (Bruker AXS Inc., 2017)'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'XS, VERSION 2013/1'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  'APEX3 (Bruker AXS Inc., 2017)'

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
C C1 0.12292(3) -0.0112(2) 0.46673(8) 0.0179(2) Uani d . . . 1 . .
C C2 0.15082(3) 0.1502(2) 0.49065(8) 0.0189(2) Uani d . . . 1 . .
H H2 0.150021 0.264029 0.545474 0.023 Uiso calc U . R 1 . .
C C3 0.18031(3) 0.14086(19) 0.43157(8) 0.0176(2) Uani d . . . 1 . .
C C4 0.21049(3) 0.4569(2) 0.53094(10) 0.0256(2) Uani d . . . 1 . .
H H4A 0.190129 0.568893 0.51728 0.038 Uiso calc U . R 1 . .
H H4B 0.233314 0.547068 0.535784 0.038 Uiso calc U . R 1 . .
H H4C 0.208481 0.371899 0.596769 0.038 Uiso calc U . R 1 . .
C C5 0.18100(3) -0.02834(19) 0.35089(8) 0.01560(19) Uani d . . . 1 . .
C C6 0.21334(3) 0.1248(2) 0.21809(9) 0.0236(2) Uani d . . . 1 . .
H H6A 0.19367 0.098332 0.162399 0.035 Uiso calc U . R 1 . .
H H6B 0.236701 0.110322 0.189519 0.035 Uiso calc U . R 1 . .
H H6C 0.211111 0.286583 0.24741 0.035 Uiso calc U . R 1 . .
C C7 0.15192(3) -0.18629(18) 0.32877(8) 0.01616(19) Uani d . . . 1 . .
C C8 0.12572(3) -0.5087(2) 0.22521(9) 0.0220(2) Uani d . . . 1 . .
H H8A 0.122913 -0.61033 0.286057 0.033 Uiso calc U . R 1 . .
H H8B 0.130702 -0.610613 0.166231 0.033 Uiso calc U . R 1 . .
H H8C 0.103368 -0.417316 0.206777 0.033 Uiso calc U . R 1 . .
C C9 0.12228(3) -0.17964(19) 0.38772(8) 0.0180(2) Uani d . . . 1 . .
H H9 0.102446 -0.287259 0.373814 0.022 Uiso calc U . R 1 . .
C C10 0.06627(3) 0.12278(19) 0.52107(8) 0.01647(19) Uani d . . . 1 . .
C C11 0.05184(4) -0.1131(3) 0.67109(11) 0.0329(3) Uani d . . . 1 . .
H H11A 0.060324 -0.257859 0.637372 0.049 Uiso calc U . R 1 . .
H H11B 0.029853 -0.151424 0.703783 0.049 Uiso calc U . R 1 . .
H H11C 0.070703 -0.056778 0.724464 0.049 Uiso calc U . R 1 . .
C C12 0.01154(3) 0.2206(2) 0.60143(10) 0.0262(2) Uani d . . . 1 . .
H H12A 0.016655 0.342227 0.656173 0.039 Uiso calc U . R 1 . .
H H12B -0.008193 0.115918 0.619135 0.039 Uiso calc U . R 1 . .
H H12C 0.004407 0.300986 0.534711 0.039 Uiso calc U . R 1 . .
N N1 0.04386(3) 0.07622(18) 0.59290(7) 0.0206(2) Uani d . . . 1 . .
O O1 0.09538(2) -0.02473(15) 0.53414(6) 0.02069(17) Uani d . . . 1 . .
O O2 0.20984(2) 0.28523(16) 0.44749(7) 0.02357(18) Uani d . . . 1 . .
O O3 0.21118(2) -0.05195(14) 0.29851(6) 0.01863(16) Uani d . . . 1 . .
O O4 0.15513(2) -0.34519(14) 0.24933(6) 0.02006(17) Uani d . . . 1 . .
S S1 0.05967(2) 0.33032(5) 0.42799(2) 0.02195(9) Uani d . . . 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
C1 C2 . 1.3790(16) ?
C1 C9 . 1.3801(15) ?
C1 O1 . 1.4105(12) ?
C2 C3 . 1.3979(15) ?
C3 O2 . 1.3555(13) ?
C3 C5 . 1.4026(14) ?
C4 O2 . 1.4344(13) ?
C5 O3 . 1.3728(12) ?
C5 C7 . 1.3962(15) ?
C6 O3 . 1.4347(13) ?
C7 O4 . 1.3651(12) ?
C7 C9 . 1.4011(14) ?
C8 O4 . 1.4280(13) ?
C10 N1 . 1.3325(13) ?
C10 O1 . 1.3515(13) ?
C10 S1 . 1.6619(11) ?
C11 N1 . 1.4639(15) ?
C12 N1 . 1.4558(15) ?

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
C2 C1 C9 . . 123.98(9) ?
C2 C1 O1 . . 118.18(9) ?
C9 C1 O1 . . 117.41(10) ?
C1 C2 C3 . . 117.81(10) ?
O2 C3 C2 . . 124.22(10) ?
O2 C3 C5 . . 115.48(9) ?
C2 C3 C5 . . 120.29(10) ?
O3 C5 C7 . . 119.52(9) ?
O3 C5 C3 . . 120.47(9) ?
C7 C5 C3 . . 119.83(9) ?
O4 C7 C5 . . 115.59(9) ?
O4 C7 C9 . . 123.95(10) ?
C5 C7 C9 . . 120.45(9) ?
C1 C9 C7 . . 117.63(10) ?
N1 C10 O1 . . 110.18(9) ?
N1 C10 S1 . . 125.44(9) ?
O1 C10 S1 . . 124.38(8) ?
C10 N1 C12 . . 121.65(10) ?
C10 N1 C11 . . 121.39(10) ?
C12 N1 C11 . . 116.86(9) ?
C10 O1 C1 . . 120.80(8) ?
C3 O2 C4 . . 117.10(9) ?
C5 O3 C6 . . 113.56(8) ?
C7 O4 C8 . . 116.65(8) ?

####################################################################### 
# 
# 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_fg749m
_database_code_depnum_ccdc_archive 'CCDC 1831297'
loop_
_audit_author_name
_audit_author_address
'Rakesh Ganguly'
;Nanyang Technological University
Singapore
;
_audit_update_record             
;
2018-03-21 deposited with the CCDC.	2020-10-30 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H13 N O2 S'
_chemical_formula_iupac          ?
_chemical_formula_weight         211.27

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_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                   8.7175(4)
_cell_length_b                   9.9546(4)
_cell_length_c                   12.4668(5)
_cell_angle_alpha                90
_cell_angle_beta                 99.0234(16)
_cell_angle_gamma                90
_cell_volume                     1068.47(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7134
_cell_measurement_theta_min      2.6312
_cell_measurement_theta_max      30.9102
_cell_measurement_temperature    123.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            'light yellow'
_exptl_crystal_size_max          0.474
_exptl_crystal_size_mid          0.395
_exptl_crystal_size_min          0.228
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             448

_exptl_absorpt_coefficient_mu    0.277
_exptl_absorpt_correction_type   'Numerical Mu Calculated'
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.75
_exptl_absorpt_correction_T_max  0.94

_exptl_special_details           
;
;

_diffrn_ambient_temperature      123.(2)

_diffrn_source                   'Incoatec microfocus source'
_diffrn_source_type              'Bruker D8 Quest'

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'Multilayer Mirror'

_diffrn_measurement_device_type  'Photon II CPADs detector'
_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 7.4074

_diffrn_reflns_number            20239
_diffrn_reflns_av_R_equivalents  0.0819
_diffrn_reflns_av_unetI/netI     0.0533
_diffrn_reflns_theta_min         2.63
_diffrn_reflns_theta_max         31.01
_diffrn_reflns_theta_full        31.01
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18

_refine_special_details          
;
;

_reflns_number_total             3393
_reflns_number_gt                2661
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0610
_refine_ls_R_factor_gt           0.0420
_refine_ls_wR_factor_gt          0.0977
_refine_ls_wR_factor_ref         0.1094
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_refine_ls_number_reflns         3393
_refine_ls_number_parameters     130
_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)+(0.0403P)²+0.3768P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.340
_refine_diff_density_min         -0.284
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'APEX3 (Bruker AXS Inc., 2017)'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'XS, VERSION 2013/1'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  'APEX3 (Bruker AXS Inc., 2017)'

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
C C1 0.27586(16) 0.59734(14) 0.45215(11) 0.0237(3) Uani d . . . 1 . .
C C2 0.33861(17) 0.67232(14) 0.37735(12) 0.0253(3) Uani d . . . 1 . .
H H2 0.416127 0.737601 0.400824 0.03 Uiso calc U . R 1 . .
C C3 0.28805(17) 0.65221(14) 0.26685(12) 0.0250(3) Uani d . . . 1 . .
H H3 0.33205 0.702486 0.214481 0.03 Uiso calc U . R 1 . .
C C4 0.17298(15) 0.55818(13) 0.23403(11) 0.0220(3) Uani d . . . 1 . .
C C5 0.1823(2) 0.60052(17) 0.04676(12) 0.0343(4) Uani d . . . 1 . .
H H5A 0.166154 0.697379 0.053593 0.052 Uiso calc U . R 1 . .
H H5B 0.133453 0.570392 -0.025404 0.052 Uiso calc U . R 1 . .
H H5C 0.29387 0.581414 0.056436 0.052 Uiso calc U . R 1 . .
C C6 0.11033(16) 0.48354(14) 0.31080(11) 0.0249(3) Uani d . . . 1 . .
H H6 0.031132 0.419522 0.287886 0.03 Uiso calc U . R 1 . .
C C7 0.16254(17) 0.50190(14) 0.42025(12) 0.0261(3) Uani d . . . 1 . .
H H7 0.12126 0.44976 0.472831 0.031 Uiso calc U . R 1 . .
C C8 0.26827(15) 0.70216(13) 0.62278(11) 0.0206(3) Uani d . . . 1 . .
C C9 0.47555(17) 0.61835(15) 0.76306(12) 0.0302(3) Uani d . . . 1 . .
H H9A 0.439914 0.533261 0.790103 0.045 Uiso calc U . R 1 . .
H H9B 0.543847 0.664116 0.821724 0.045 Uiso calc U . R 1 . .
H H9C 0.532721 0.600484 0.70287 0.045 Uiso calc U . R 1 . .
C C10 0.28518(19) 0.79085(17) 0.80448(12) 0.0331(3) Uani d . . . 1 . .
H H10A 0.293817 0.884947 0.783092 0.05 Uiso calc U . R 1 . .
H H10B 0.347972 0.776229 0.875885 0.05 Uiso calc U . R 1 . .
H H10C 0.176299 0.769793 0.80811 0.05 Uiso calc U . R 1 . .
N N1 0.34082(14) 0.70409(12) 0.72479(9) 0.0235(2) Uani d . . . 1 . .
O O1 0.11430(12) 0.53116(11) 0.12784(8) 0.0291(2) Uani d . . . 1 . .
O O2 0.33507(12) 0.61100(11) 0.56320(8) 0.0296(2) Uani d . . . 1 . .
S S1 0.11627(4) 0.79641(4) 0.57294(3) 0.02570(11) Uani d . . . 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
C1 C2 . 1.373(2) ?
C1 C7 . 1.383(2) ?
C1 O2 . 1.4061(16) ?
C2 C3 . 1.3934(19) ?
C3 C4 . 1.3860(19) ?
C4 O1 . 1.3690(16) ?
C4 C6 . 1.389(2) ?
C5 O1 . 1.4273(19) ?
C6 C7 . 1.3812(19) ?
C8 N1 . 1.3286(17) ?
C8 O2 . 1.3602(16) ?
C8 S1 . 1.6625(14) ?
C9 N1 . 1.4696(18) ?
C10 N1 . 1.4558(19) ?

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
C2 C1 C7 . . 121.37(13) ?
C2 C1 O2 . . 119.48(13) ?
C7 C1 O2 . . 119.00(13) ?
C1 C2 C3 . . 119.69(13) ?
C4 C3 C2 . . 119.41(13) ?
O1 C4 C3 . . 124.16(13) ?
O1 C4 C6 . . 115.69(12) ?
C3 C4 C6 . . 120.15(12) ?
C7 C6 C4 . . 120.37(13) ?
C6 C7 C1 . . 118.99(13) ?
N1 C8 O2 . . 110.62(11) ?
N1 C8 S1 . . 125.55(11) ?
O2 C8 S1 . . 123.84(10) ?
C8 N1 C10 . . 120.15(12) ?
C8 N1 C9 . . 122.58(12) ?
C10 N1 C9 . . 117.25(11) ?
C4 O1 C5 . . 117.14(11) ?
C8 O2 C1 . . 118.66(10) ?

####################################################################### 
# 
# 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_fg770m
_database_code_depnum_ccdc_archive 'CCDC 1831300'
loop_
_audit_author_name
_audit_author_address
'Rakesh Ganguly'
;Nanyang Technological University
Singapore
;
_audit_update_record             
;
2018-03-21 deposited with the CCDC.	2020-10-30 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H10 Cl N O S'
_chemical_formula_iupac          ?
_chemical_formula_weight         215.69

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_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                   8.1419(2)
_cell_length_b                   9.5362(3)
_cell_length_c                   13.6861(4)
_cell_angle_alpha                90
_cell_angle_beta                 105.4170(10)
_cell_angle_gamma                90
_cell_volume                     1024.39(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6530
_cell_measurement_theta_min      2.5950
_cell_measurement_theta_max      32.6725
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.080
_exptl_crystal_density_diffrn    1.399
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             448

_exptl_absorpt_coefficient_mu    0.536
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.82
_exptl_absorpt_correction_T_max  0.96

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'Incoatec microfocus source'
_diffrn_source_type              'Bruker D8 Quest'

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'Multilayer Mirror'

_diffrn_measurement_device_type  'Photon II CPADs detector'
_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 7.4074

_diffrn_reflns_number            20160
_diffrn_reflns_av_R_equivalents  0.0461
_diffrn_reflns_av_unetI/netI     0.0391
_diffrn_reflns_theta_min         2.60
_diffrn_reflns_theta_max         33.15
_diffrn_reflns_theta_full        33.15
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       21

_refine_special_details          
;
;

_reflns_number_total             3900
_reflns_number_gt                3064
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0569
_refine_ls_R_factor_gt           0.0382
_refine_ls_wR_factor_gt          0.0782
_refine_ls_wR_factor_ref         0.0878
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_refine_ls_number_reflns         3900
_refine_ls_number_parameters     120
_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)+(0.0296P)²+0.4725P] 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         0.442
_refine_diff_density_min         -0.492
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'
Cl Cl 0.1484 0.1585 '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'

_computing_data_collection       'APEX3 (Bruker AXS Inc., 2017)'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'XS, VERSION 2013/1'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  'APEX3 (Bruker AXS Inc., 2017)'

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
C C1 0.17682(16) 0.87701(13) 0.11951(10) 0.0192(2) Uani d . . . 1 . .
C C2 0.02466(17) 0.80751(14) 0.11084(11) 0.0235(3) Uani d . . . 1 . .
H H2 -0.027257 0.755976 0.051224 0.028 Uiso calc U . R 1 . .
C C3 -0.05128(16) 0.81386(14) 0.19011(11) 0.0231(3) Uani d . . . 1 . .
H H3 -0.156029 0.766975 0.185449 0.028 Uiso calc U . R 1 . .
C C4 0.02722(16) 0.88918(13) 0.27591(10) 0.0191(2) Uani d . . . 1 . .
C C5 0.18130(17) 0.95631(13) 0.28553(10) 0.0212(2) Uani d . . . 1 . .
H H5 0.235036 1.005372 0.345989 0.025 Uiso calc U . R 1 . .
C C6 0.25623(16) 0.95102(14) 0.20573(10) 0.0211(2) Uani d . . . 1 . .
H H6 0.361036 0.997819 0.210369 0.025 Uiso calc U . R 1 . .
C C7 0.37009(15) 0.79378(12) 0.02877(9) 0.0174(2) Uani d . . . 1 . .
C C8 0.31042(17) 0.90239(14) -0.13855(10) 0.0224(3) Uani d . . . 1 . .
H H8A 0.19076 0.905367 -0.137128 0.034 Uiso calc U . R 1 . .
H H8B 0.317602 0.869919 -0.205223 0.034 Uiso calc U . R 1 . .
H H8C 0.359918 0.996454 -0.125656 0.034 Uiso calc U . R 1 . .
C C9 0.55027(17) 0.73248(15) -0.07950(10) 0.0236(3) Uani d . . . 1 . .
H H9A 0.65569 0.780371 -0.043894 0.035 Uiso calc U . R 1 . .
H H9B 0.540266 0.732023 -0.15246 0.035 Uiso calc U . R 1 . .
H H9C 0.552657 0.635749 -0.054989 0.035 Uiso calc U . R 1 . .
Cl Cl1 -0.07237(5) 0.90495(4) 0.37312(3) 0.03140(10) Uani d . . . 1 . .
N N1 0.40443(13) 0.80599(11) -0.06037(8) 0.0181(2) Uani d . . . 1 . .
O O1 0.24167(12) 0.88215(10) 0.03442(7) 0.0241(2) Uani d . . . 1 . .
S S1 0.46836(4) 0.68791(4) 0.12267(2) 0.02224(8) Uani d . . . 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
C1 C6 . 1.3795(18) ?
C1 C2 . 1.3820(19) ?
C1 O1 . 1.4014(15) ?
C2 C3 . 1.3854(19) ?
C3 C4 . 1.3800(19) ?
C4 C5 . 1.3832(18) ?
C4 Cl1 . 1.7388(12) ?
C5 C6 . 1.3863(18) ?
C7 N1 . 1.3272(15) ?
C7 O1 . 1.3609(14) ?
C7 S1 . 1.6626(13) ?
C8 N1 . 1.4629(16) ?
C9 N1 . 1.4613(16) ?

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
C6 C1 C2 . . 121.63(12) ?
C6 C1 O1 . . 119.90(12) ?
C2 C1 O1 . . 118.20(12) ?
C1 C2 C3 . . 119.23(12) ?
C4 C3 C2 . . 119.14(12) ?
C3 C4 C5 . . 121.67(12) ?
C3 C4 Cl1 . . 119.44(10) ?
C5 C4 Cl1 . . 118.87(10) ?
C4 C5 C6 . . 119.09(12) ?
C1 C6 C5 . . 119.22(12) ?
N1 C7 O1 . . 110.53(10) ?
N1 C7 S1 . . 126.02(9) ?
O1 C7 S1 . . 123.45(9) ?
C7 N1 C9 . . 120.16(11) ?
C7 N1 C8 . . 122.02(10) ?
C9 N1 C8 . . 117.55(10) ?
C7 O1 C1 . . 119.37(10) ?

####################################################################### 
# 
# 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_fg792
_database_code_depnum_ccdc_archive 'CCDC 1831299'
loop_
_audit_author_name
_audit_author_address
'Rakesh Ganguly'
;Nanyang Technological University
Singapore
;
_audit_update_record             
;
2018-03-21 deposited with the CCDC.	2020-10-30 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H9 F6 N O S'
_chemical_formula_iupac          ?
_chemical_formula_weight         317.25
_chemical_absolute_configuration ?

_chemical_melting_point          ?

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

_cell_length_a                   10.683(5)
_cell_length_b                   15.115(7)
_cell_length_c                   8.801(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1421.1(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4905
_cell_measurement_theta_min      2.3345
_cell_measurement_theta_max      22.4004
_cell_measurement_temperature    298.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.200
_exptl_crystal_density_diffrn    1.483
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             640

_exptl_absorpt_coefficient_mu    0.289
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.86
_exptl_absorpt_correction_T_max  0.94

_exptl_special_details           
;
;

_diffrn_ambient_temperature      298.(2)

_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'Bruker KappaCCD'

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            18547
_diffrn_reflns_av_R_equivalents  0.0342
_diffrn_reflns_av_unetI/netI     0.0282
_diffrn_reflns_theta_min         1.35
_diffrn_reflns_theta_max         27.11
_diffrn_reflns_theta_full        27.11
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11

_refine_special_details          
;

Refined as a 2-component perfect inversion twin.
;

_reflns_number_total             3047
_reflns_number_gt                1951
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0785
_refine_ls_R_factor_gt           0.0376
_refine_ls_wR_factor_gt          0.0790
_refine_ls_wR_factor_ref         0.0987
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.031
_refine_ls_number_reflns         3047
_refine_ls_number_parameters     239
_refine_ls_number_restraints     151
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0372P)²+0.2595P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.115
_refine_diff_density_min         -0.110
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.0080(19)
_refine_ls_abs_structure_details 
;

Refined as a perfect inversion twin.
;
_refine_ls_abs_structure_Flack   0.500000

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'

_computing_data_collection       'APEX3 (Bruker AXS Inc., 2016)'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'XS, VERSION 2013/1'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'XP (Bruker AXS Inc., 2016)'
_computing_publication_material  'APEX3 (Bruker AXS Inc., 2016)'

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
C C1 0.2809(3) 0.7289(2) 0.9210(5) 0.0603(9) Uani d . . . 1.0 . .
C C2 0.2825(4) 0.6548(2) 0.8299(5) 0.0723(12) Uani d . . . 1.0 . .
H H2 0.209953 0.635313 0.782007 0.087 Uiso calc U . R 1.0 . .
C C3 0.3943(4) 0.6101(2) 0.8114(6) 0.0751(11) Uani d . . . 1.0 . .
C C4 0.3959(9) 0.5268(5) 0.7148(10) 0.126(3) Uani d . . . 1.0 . .
C C5 0.5017(4) 0.6388(3) 0.8802(5) 0.0757(12) Uani d . . . 1.0 . .
H H5 0.576383 0.608318 0.866048 0.091 Uiso calc U . R 1.0 . .
C C6 0.4985(3) 0.7139(2) 0.9714(5) 0.0670(10) Uani d . . . 1.0 . .
C C7 0.6148(5) 0.7471(4) 1.0448(9) 0.0981(16) Uani d . . . 1.0 . .
C C8 0.3866(4) 0.7590(2) 0.9922(4) 0.0634(10) Uani d . . . 1.0 . .
H H8 0.383503 0.808974 1.053603 0.076 Uiso calc U . R 1.0 . .
C C9 0.1434(3) 0.8543(2) 0.9154(4) 0.0580(9) Uani d . . . 1.0 . .
C C10 -0.0030(6) 0.9722(4) 0.9656(9) 0.124(2) Uani d . . . 1.0 . .
H H10A 0.066894 1.010715 0.947542 0.185 Uiso calc U . R 1.0 . .
H H10B -0.047085 0.991463 1.054747 0.185 Uiso calc U . R 1.0 . .
H H10C -0.058388 0.973872 0.879738 0.185 Uiso calc U . R 1.0 . .
C C11 -0.0266(4) 0.8278(4) 1.0981(7) 0.0966(15) Uani d . . . 1.0 . .
H H11A -0.047828 0.772038 1.052691 0.145 Uiso calc U . R 1.0 . .
H H11B -0.10178 0.857971 1.127912 0.145 Uiso calc U . R 1.0 . .
H H11C 0.024848 0.81789 1.185901 0.145 Uiso calc U . R 1.0 . .
F F1 0.5998(11) 0.8046(16) 1.157(2) 0.145(7) Uani d U P D 0.474(18) A 1
F F2 0.694(3) 0.6901(15) 1.080(3) 0.146(10) Uani d U P D 0.474(18) A 1
F F3 0.6824(17) 0.8027(16) 0.942(2) 0.157(8) Uani d U P D 0.474(18) A 1
F F4 0.503(2) 0.4951(19) 0.698(4) 0.166(11) Uani d U P D 0.474(18) A 1
F F5 0.328(2) 0.4596(6) 0.800(2) 0.170(7) Uani d U P D 0.474(18) A 1
F F6 0.345(2) 0.5326(12) 0.5928(19) 0.147(8) Uani d U P D 0.474(18) A 1
F F1A 0.6388(18) 0.8222(8) 1.018(3) 0.174(10) Uani d U P D 0.526(18) A 2
F F2A 0.5952(13) 0.7372(15) 1.2012(14) 0.167(5) Uani d U P D 0.526(18) A 2
F F3A 0.712(2) 0.6961(15) 1.029(3) 0.166(10) Uani d U P D 0.526(18) A 2
F F4A 0.470(3) 0.4700(14) 0.751(3) 0.175(13) Uani d U P D 0.526(18) A 2
F F5A 0.2890(16) 0.5059(15) 0.661(3) 0.191(13) Uani d U P D 0.526(18) A 2
F F6A 0.457(3) 0.5548(11) 0.5723(19) 0.219(9) Uani d U P D 0.526(18) A 2
N N1 0.0419(3) 0.8819(2) 0.9881(4) 0.0707(9) Uani d . . . 1.0 . .
O O1 0.1641(2) 0.76707(16) 0.9510(4) 0.0779(9) Uani d . . . 1.0 . .
S S1 0.23097(9) 0.91080(6) 0.79534(15) 0.0725(3) Uani d . . . 1.0 . .


_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
C1 C8 . 1.370(5) ?
C1 C2 . 1.377(5) ?
C1 O1 . 1.400(4) ?
C2 C3 . 1.383(5) ?
C3 C5 . 1.368(6) ?
C3 C4 . 1.519(8) ?
C4 F6 . 1.206(15) ?
C4 F4A . 1.212(19) ?
C4 F4 . 1.25(2) ?
C4 F5A . 1.278(16) ?
C4 F5 . 1.456(14) ?
C4 F6A . 1.48(2) ?
C5 C6 . 1.390(5) ?
C6 C8 . 1.388(5) ?
C6 C7 . 1.488(6) ?
C7 F1A . 1.188(13) ?
C7 F2 . 1.245(19) ?
C7 F3A . 1.30(2) ?
C7 F1 . 1.323(13) ?
C7 F2A . 1.400(15) ?
C7 F3 . 1.430(17) ?
C9 N1 . 1.326(5) ?
C9 O1 . 1.374(4) ?
C9 S1 . 1.649(4) ?
C10 N1 . 1.460(6) ?
C11 N1 . 1.464(6) ?

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
C8 C1 C2 . . 121.8(4) ?
C8 C1 O1 . . 120.8(3) ?
C2 C1 O1 . . 117.2(4) ?
C1 C2 C3 . . 118.5(4) ?
C5 C3 C2 . . 121.1(4) ?
C5 C3 C4 . . 120.1(5) ?
C2 C3 C4 . . 118.8(5) ?
F6 C4 F4 . . 109.2(16) ?
F4A C4 F5A . . 120.5(16) ?
F6 C4 F5 . . 106.6(14) ?
F4 C4 F5 . . 104.6(14) ?
F4A C4 F6A . . 97.8(15) ?
F5A C4 F6A . . 98.7(14) ?
F6 C4 C3 . . 115.7(9) ?
F4A C4 C3 . . 116.6(13) ?
F4 C4 C3 . . 113.3(15) ?
F5A C4 C3 . . 113.8(10) ?
F5 C4 C3 . . 106.6(7) ?
F6A C4 C3 . . 104.0(9) ?
C3 C5 C6 . . 119.6(4) ?
C8 C6 C5 . . 119.9(4) ?
C8 C6 C7 . . 119.8(4) ?
C5 C6 C7 . . 120.4(4) ?
F1A C7 F3A . . 111.9(15) ?
F2 C7 F1 . . 110.7(16) ?
F1A C7 F2A . . 109.2(13) ?
F3A C7 F2A . . 99.5(13) ?
F2 C7 F3 . . 102.6(16) ?
F1 C7 F3 . . 98.4(11) ?
F1A C7 C6 . . 114.6(8) ?
F2 C7 C6 . . 116.2(15) ?
F3A C7 C6 . . 114.7(13) ?
F1 C7 C6 . . 116.3(7) ?
F2A C7 C6 . . 105.4(8) ?
F3 C7 C6 . . 110.2(10) ?
C1 C8 C6 . . 119.1(4) ?
N1 C9 O1 . . 108.9(3) ?
N1 C9 S1 . . 127.6(3) ?
O1 C9 S1 . . 123.5(3) ?
C9 N1 C10 . . 119.8(4) ?
C9 N1 C11 . . 123.5(3) ?
C10 N1 C11 . . 116.6(4) ?
C9 O1 C1 . . 119.8(3) ?

####################################################################### 
# 
# 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_fg796m
_database_code_depnum_ccdc_archive 'CCDC 1831301'
loop_
_audit_author_name
_audit_author_address
'Rakesh Ganguly'
;Nanyang Technological University
Singapore
;
_audit_update_record             
;
2018-03-21 deposited with the CCDC.	2020-10-30 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H15 N O S'
_chemical_formula_iupac          ?
_chemical_formula_weight         209.30

_chemical_melting_point          ?

_space_group_crystal_system      triclinic
_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                   7.3200(3)
_cell_length_b                   11.5744(5)
_cell_length_c                   13.5992(5)
_cell_angle_alpha                80.8887(15)
_cell_angle_beta                 80.9328(14)
_cell_angle_gamma                80.5041(17)
_cell_volume                     1111.79(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5437
_cell_measurement_theta_min      2.5171
_cell_measurement_theta_max      30.5902
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.040
_exptl_crystal_density_diffrn    1.250
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             448

_exptl_absorpt_coefficient_mu    0.259
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.87
_exptl_absorpt_correction_T_max  0.99

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'Incoatec microfocus source'
_diffrn_source_type              'Bruker D8 Quest'

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'Multilayer Mirror'

_diffrn_measurement_device_type  'Photon II CPADs detector'
_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 7.4074

_diffrn_reflns_number            22005
_diffrn_reflns_av_R_equivalents  0.0556
_diffrn_reflns_av_unetI/netI     0.0721
_diffrn_reflns_theta_min         2.20
_diffrn_reflns_theta_max         31.06
_diffrn_reflns_theta_full        31.06
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.984
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19

_refine_special_details          
;
;

_reflns_number_total             7017
_reflns_number_gt                4894
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0866
_refine_ls_R_factor_gt           0.0513
_refine_ls_wR_factor_gt          0.1032
_refine_ls_wR_factor_ref         0.1189
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_refine_ls_number_reflns         7017
_refine_ls_number_parameters     261
_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)+(0.0398P)²+0.4534P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.366
_refine_diff_density_min         -0.376
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'APEX3 (Bruker AXS Inc., 2017)'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'XS, VERSION 2013/1'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  'APEX3 (Bruker AXS Inc., 2017)'

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
C C1 0.4017(2) 0.33512(15) 0.48633(12) 0.0170(3) Uani d . . . 1 . .
C C2 0.3122(2) 0.44936(15) 0.46506(12) 0.0160(3) Uani d . . . 1 . .
C C3 0.2068(2) 0.51725(16) 0.54667(13) 0.0205(3) Uani d . . . 1 . .
H H3A 0.097061 0.480018 0.578016 0.031 Uiso calc U . R 1 . .
H H3B 0.166315 0.598846 0.517845 0.031 Uiso calc U . R 1 . .
H H3C 0.288056 0.517221 0.597452 0.031 Uiso calc U . R 1 . .
C C4 0.3237(2) 0.49881(16) 0.36412(12) 0.0194(3) Uani d . . . 1 . .
H H4 0.265791 0.577547 0.346642 0.023 Uiso calc U . R 1 . .
C C5 0.4183(2) 0.43484(17) 0.28921(13) 0.0225(4) Uani d . . . 1 . .
H H5 0.422394 0.469126 0.220784 0.027 Uiso calc U . R 1 . .
C C6 0.5069(2) 0.32106(17) 0.31367(13) 0.0239(4) Uani d . . . 1 . .
H H6 0.570996 0.277765 0.261605 0.029 Uiso calc U . R 1 . .
C C7 0.5037(2) 0.26896(16) 0.41345(13) 0.0207(4) Uani d . . . 1 . .
C C8 0.6072(3) 0.14809(17) 0.44338(16) 0.0323(4) Uani d . . . 1 . .
H H8A 0.665389 0.113051 0.382916 0.048 Uiso calc U . R 1 . .
H H8B 0.519453 0.09769 0.483254 0.048 Uiso calc U . R 1 . .
H H8C 0.704117 0.154805 0.483483 0.048 Uiso calc U . R 1 . .
C C9 0.2927(2) 0.21107(15) 0.63512(12) 0.0186(3) Uani d . . . 1 . .
C C10 0.5022(3) 0.19847(17) 0.76092(14) 0.0267(4) Uani d . . . 1 . .
H H10A 0.610011 0.196593 0.708099 0.04 Uiso calc U . R 1 . .
H H10B 0.534064 0.142983 0.820085 0.04 Uiso calc U . R 1 . .
H H10C 0.468353 0.278549 0.779244 0.04 Uiso calc U . R 1 . .
C C11 0.2392(3) 0.08013(17) 0.79249(13) 0.0272(4) Uani d . . . 1 . .
H H11A 0.123735 0.075193 0.766422 0.041 Uiso calc U . R 1 . .
H H11B 0.208336 0.106578 0.85889 0.041 Uiso calc U . R 1 . .
H H11C 0.315767 0.002094 0.79815 0.041 Uiso calc U . R 1 . .
C C12 0.0353(2) 0.30918(15) 0.01078(12) 0.0170(3) Uani d . . . 1 . .
C C13 0.1570(2) 0.38309(15) -0.04437(12) 0.0180(3) Uani d . . . 1 . .
C C14 0.3012(3) 0.42423(17) 0.00406(15) 0.0263(4) Uani d . . . 1 . .
H H14A 0.369736 0.4785 -0.045254 0.039 Uiso calc U . R 1 . .
H H14B 0.388689 0.355871 0.028187 0.039 Uiso calc U . R 1 . .
H H14C 0.239274 0.465135 0.060831 0.039 Uiso calc U . R 1 . .
C C15 0.1405(2) 0.41616(16) -0.14554(13) 0.0213(4) Uani d . . . 1 . .
H H15 0.22111 0.46698 -0.185608 0.026 Uiso calc U . R 1 . .
C C16 0.0080(3) 0.37601(16) -0.18890(13) 0.0225(4) Uani d . . . 1 . .
H H16 -0.001175 0.39901 -0.258378 0.027 Uiso calc U . R 1 . .
C C17 -0.1106(2) 0.30265(16) -0.13140(13) 0.0216(4) Uani d . . . 1 . .
H H17 -0.200792 0.275537 -0.161945 0.026 Uiso calc U . R 1 . .
C C18 -0.1004(2) 0.26765(15) -0.02909(12) 0.0187(3) Uani d . . . 1 . .
C C19 -0.2266(3) 0.18663(17) 0.03411(14) 0.0277(4) Uani d . . . 1 . .
H H19A -0.154352 0.108729 0.050871 0.042 Uiso calc U . R 1 . .
H H19B -0.326788 0.178759 -0.00338 0.042 Uiso calc U . R 1 . .
H H19C -0.281154 0.219501 0.096111 0.042 Uiso calc U . R 1 . .
C C20 0.1451(2) 0.18542(15) 0.15397(12) 0.0184(3) Uani d . . . 1 . .
C C21 0.0348(2) 0.27855(16) 0.30596(12) 0.0209(4) Uani d . . . 1 . .
H H21A 0.053094 0.354532 0.265145 0.031 Uiso calc U . R 1 . .
H H21B 0.081088 0.274388 0.370414 0.031 Uiso calc U . R 1 . .
H H21C -0.098663 0.271274 0.317959 0.031 Uiso calc U . R 1 . .
C C22 0.2268(3) 0.07817(16) 0.31217(13) 0.0255(4) Uani d . . . 1 . .
H H22A 0.164055 0.01016 0.310272 0.038 Uiso calc U . R 1 . .
H H22B 0.217456 0.093049 0.381878 0.038 Uiso calc U . R 1 . .
H H22C 0.358703 0.061432 0.284277 0.038 Uiso calc U . R 1 . .
N N1 0.3433(2) 0.16442(13) 0.72396(10) 0.0210(3) Uani d . . . 1 . .
N N2 0.1375(2) 0.18218(13) 0.25276(10) 0.0190(3) Uani d . . . 1 . .
O O1 0.40959(17) 0.28904(11) 0.58792(8) 0.0204(3) Uani d . . . 1 . .
O O2 0.03840(17) 0.28480(11) 0.11543(8) 0.0205(3) Uani d . . . 1 . .
S S1 0.11243(6) 0.18344(4) 0.58550(3) 0.02261(11) Uani d . . . 1 . .
S S2 0.26643(7) 0.08487(4) 0.08497(3) 0.02599(12) Uani d . . . 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
C1 C2 . 1.383(2) ?
C1 C7 . 1.395(2) ?
C1 O1 . 1.4064(19) ?
C2 C4 . 1.396(2) ?
C2 C3 . 1.500(2) ?
C4 C5 . 1.383(2) ?
C5 C6 . 1.383(3) ?
C6 C7 . 1.393(3) ?
C7 C8 . 1.505(3) ?
C9 N1 . 1.325(2) ?
C9 O1 . 1.363(2) ?
C9 S1 . 1.6696(17) ?
C10 N1 . 1.469(2) ?
C11 N1 . 1.461(2) ?
C12 C18 . 1.386(2) ?
C12 C13 . 1.388(2) ?
C12 O2 . 1.4094(19) ?
C13 C15 . 1.387(2) ?
C13 C14 . 1.503(2) ?
C15 C16 . 1.386(2) ?
C16 C17 . 1.381(3) ?
C17 C18 . 1.396(2) ?
C18 C19 . 1.501(2) ?
C20 N2 . 1.331(2) ?
C20 O2 . 1.360(2) ?
C20 S2 . 1.6630(17) ?
C21 N2 . 1.463(2) ?
C22 N2 . 1.459(2) ?

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
C2 C1 C7 . . 123.81(15) ?
C2 C1 O1 . . 117.69(14) ?
C7 C1 O1 . . 118.01(15) ?
C1 C2 C4 . . 117.08(15) ?
C1 C2 C3 . . 121.59(15) ?
C4 C2 C3 . . 121.33(15) ?
C5 C4 C2 . . 120.96(17) ?
C4 C5 C6 . . 120.17(16) ?
C5 C6 C7 . . 121.04(16) ?
C6 C7 C1 . . 116.88(17) ?
C6 C7 C8 . . 122.60(16) ?
C1 C7 C8 . . 120.51(16) ?
N1 C9 O1 . . 109.89(14) ?
N1 C9 S1 . . 126.85(13) ?
O1 C9 S1 . . 123.25(12) ?
C18 C12 C13 . . 123.99(15) ?
C18 C12 O2 . . 118.21(15) ?
C13 C12 O2 . . 117.49(14) ?
C15 C13 C12 . . 117.21(15) ?
C15 C13 C14 . . 121.82(16) ?
C12 C13 C14 . . 120.97(15) ?
C16 C15 C13 . . 120.84(16) ?
C17 C16 C15 . . 120.16(16) ?
C16 C17 C18 . . 121.11(16) ?
C12 C18 C17 . . 116.68(16) ?
C12 C18 C19 . . 121.56(15) ?
C17 C18 C19 . . 121.75(16) ?
N2 C20 O2 . . 110.11(14) ?
N2 C20 S2 . . 126.20(13) ?
O2 C20 S2 . . 123.68(12) ?
C9 N1 C11 . . 121.87(15) ?
C9 N1 C10 . . 121.88(15) ?
C11 N1 C10 . . 116.20(14) ?
C20 N2 C22 . . 120.04(14) ?
C20 N2 C21 . . 122.08(14) ?
C22 N2 C21 . . 117.84(13) ?
C9 O1 C1 . . 119.84(12) ?
C20 O2 C12 . . 119.44(12) ?

####################################################################### 
# 
# 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_fg809m
_database_code_depnum_ccdc_archive 'CCDC 1831307'
loop_
_audit_author_name
_audit_author_address
'Rakesh Ganguly'
;Nanyang Technological University
Singapore
;
_audit_update_record             
;
2018-03-21 deposited with the CCDC.	2020-10-30 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H10 N2 O S'
_chemical_formula_iupac          ?
_chemical_formula_weight         206.26

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_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                   8.4215(3)
_cell_length_b                   14.1614(7)
_cell_length_c                   8.8819(4)
_cell_angle_alpha                90
_cell_angle_beta                 108.134(2)
_cell_angle_gamma                90
_cell_volume                     1006.65(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6740
_cell_measurement_theta_min      2.8093
_cell_measurement_theta_max      36.2077
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.060
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             432

_exptl_absorpt_coefficient_mu    0.288
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.62
_exptl_absorpt_correction_T_max  0.98

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'Incoatec microfocus source'
_diffrn_source_type              'Bruker D8 Quest'

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'Multilayer Mirror'

_diffrn_measurement_device_type  'Photon II CPADs detector'
_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 7.4074

_diffrn_reflns_number            25455
_diffrn_reflns_av_R_equivalents  0.0989
_diffrn_reflns_av_unetI/netI     0.0722
_diffrn_reflns_theta_min         2.81
_diffrn_reflns_theta_max         36.34
_diffrn_reflns_theta_full        36.34
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14

_refine_special_details          
;
;

_reflns_number_total             4878
_reflns_number_gt                3666
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0784
_refine_ls_R_factor_gt           0.0549
_refine_ls_wR_factor_gt          0.1328
_refine_ls_wR_factor_ref         0.1504
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_refine_ls_number_reflns         4878
_refine_ls_number_parameters     129
_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)+(0.0618P)²+0.4803P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.559
_refine_diff_density_min         -0.580
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'APEX3 (Bruker AXS Inc., 2017)'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'XT, VERSION 2014/5'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  'APEX3 (Bruker AXS Inc., 2017)'

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
C C1 1.05096(17) 0.51396(11) 0.2492(2) 0.0232(3) Uani d . . . 1 . .
H H1A 1.046598 0.558482 0.163566 0.035 Uiso calc U . R 1 . .
H H1B 1.094647 0.453205 0.226882 0.035 Uiso calc U . R 1 . .
H H1C 1.124283 0.539104 0.349617 0.035 Uiso calc U . R 1 . .
C C2 0.79607(18) 0.41393(10) 0.1917(2) 0.0223(3) Uani d . . . 1 . .
H H2A 0.833954 0.361768 0.266896 0.033 Uiso calc U . R 1 . .
H H2B 0.820372 0.399225 0.093335 0.033 Uiso calc U . R 1 . .
H H2C 0.675448 0.42272 0.168924 0.033 Uiso calc U . R 1 . .
C C3 0.81528(15) 0.56739(8) 0.32469(15) 0.0133(2) Uani d . . . 1 . .
C C4 0.55693(15) 0.60973(8) 0.35839(17) 0.0143(2) Uani d . . . 1 . .
C C5 0.53416(16) 0.61896(9) 0.50509(17) 0.0154(2) Uani d . . . 1 . .
H H5 0.591192 0.578485 0.589995 0.019 Uiso calc U . R 1 . .
C C6 0.42628(16) 0.68855(9) 0.52671(17) 0.0154(2) Uani d . . . 1 . .
H H6 0.409967 0.696707 0.627042 0.019 Uiso calc U . R 1 . .
C C7 0.34249(15) 0.74614(8) 0.39918(16) 0.0143(2) Uani d . . . 1 . .
C C8 0.23776(16) 0.82201(9) 0.42043(17) 0.0160(2) Uani d . . . 1 . .
C C9 0.36219(17) 0.73300(10) 0.24999(17) 0.0179(2) Uani d . . . 1 . .
H H9 0.301371 0.770995 0.162998 0.021 Uiso calc U . R 1 . .
C C10 0.47089(17) 0.66426(9) 0.22963(17) 0.0175(2) Uani d . . . 1 . .
H H10 0.486022 0.654779 0.129091 0.021 Uiso calc U . R 1 . .
N N1 0.88342(14) 0.50069(8) 0.26056(14) 0.0155(2) Uani d . . . 1 . .
N N2 0.15704(15) 0.88542(9) 0.43374(16) 0.0211(2) Uani d . . . 1 . .
O O1 0.66427(12) 0.53927(6) 0.33693(13) 0.01717(19) Uani d . . . 1 . .
S S1 0.90119(4) 0.67176(2) 0.38971(4) 0.01688(9) Uani d . . . 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
C1 N1 . 1.4576(17) ?
C1 H1A . 0.98 ?
C1 H1B . 0.98 ?
C1 H1C . 0.98 ?
C2 N1 . 1.4645(17) ?
C2 H2A . 0.98 ?
C2 H2B . 0.98 ?
C2 H2C . 0.98 ?
C3 N1 . 1.3226(16) ?
C3 O1 . 1.3688(15) ?
C3 S1 . 1.6677(12) ?
C4 C5 . 1.3810(19) ?
C4 C10 . 1.3833(19) ?
C4 O1 . 1.3987(15) ?
C5 C6 . 1.3936(18) ?
C5 H5 . 0.95 ?
C6 C7 . 1.3959(18) ?
C6 H6 . 0.95 ?
C7 C9 . 1.3982(19) ?
C7 C8 . 1.4393(17) ?
C8 N2 . 1.1543(17) ?
C9 C10 . 1.3861(18) ?
C9 H9 . 0.95 ?
C10 H10 . 0.95 ?

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
N1 C1 H1A . . 109.5 ?
N1 C1 H1B . . 109.5 ?
H1A C1 H1B . . 109.5 ?
N1 C1 H1C . . 109.5 ?
H1A C1 H1C . . 109.5 ?
H1B C1 H1C . . 109.5 ?
N1 C2 H2A . . 109.5 ?
N1 C2 H2B . . 109.5 ?
H2A C2 H2B . . 109.5 ?
N1 C2 H2C . . 109.5 ?
H2A C2 H2C . . 109.5 ?
H2B C2 H2C . . 109.5 ?
N1 C3 O1 . . 111.40(11) ?
N1 C3 S1 . . 125.62(10) ?
O1 C3 S1 . . 122.96(9) ?
C5 C4 C10 . . 122.44(11) ?
C5 C4 O1 . . 118.78(12) ?
C10 C4 O1 . . 118.69(12) ?
C4 C5 C6 . . 119.01(12) ?
C4 C5 H5 . . 120.5 ?
C6 C5 H5 . . 120.5 ?
C5 C6 C7 . . 119.20(12) ?
C5 C6 H6 . . 120.4 ?
C7 C6 H6 . . 120.4 ?
C6 C7 C9 . . 120.81(12) ?
C6 C7 C8 . . 120.35(12) ?
C9 C7 C8 . . 118.81(12) ?
N2 C8 C7 . . 176.97(14) ?
C10 C9 C7 . . 119.68(13) ?
C10 C9 H9 . . 120.2 ?
C7 C9 H9 . . 120.2 ?
C4 C10 C9 . . 118.78(13) ?
C4 C10 H10 . . 120.6 ?
C9 C10 H10 . . 120.6 ?
C3 N1 C1 . . 119.79(11) ?
C3 N1 C2 . . 123.37(11) ?
C1 N1 C2 . . 116.78(11) ?
C3 O1 C4 . . 117.33(9) ?

####################################################################### 
# 
# 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_fg837m
_database_code_depnum_ccdc_archive 'CCDC 1831306'
loop_
_audit_author_name
_audit_author_address
'Rakesh Ganguly'
;Nanyang Technological University
Singapore
;
_audit_update_record             
;
2018-03-21 deposited with the CCDC.	2020-10-30 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H15 N O S'
_chemical_formula_iupac          ?
_chemical_formula_weight         305.38
_chemical_absolute_configuration ?

_chemical_melting_point          ?

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

_cell_length_a                   34.1190(14)
_cell_length_b                   5.5552(3)
_cell_length_c                   32.3777(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     6136.8(5)
_cell_formula_units_Z            16
_cell_measurement_reflns_used    5855
_cell_measurement_theta_min      2.2330
_cell_measurement_theta_max      28.0822
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.020
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2560

_exptl_absorpt_coefficient_mu    0.212
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.55
_exptl_absorpt_correction_T_max  1.00

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'Incoatec microfocus source'
_diffrn_source_type              'Bruker D8 Quest'

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'Multilayer Mirror'

_diffrn_measurement_device_type  'Photon II CPADs detector'
_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 7.4074

_diffrn_reflns_number            55251
_diffrn_reflns_av_R_equivalents  0.1319
_diffrn_reflns_av_unetI/netI     0.1562
_diffrn_reflns_theta_min         2.23
_diffrn_reflns_theta_max         31.05
_diffrn_reflns_theta_full        31.05
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_limit_h_min       -49
_diffrn_reflns_limit_h_max       47
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -46
_diffrn_reflns_limit_l_max       40

_refine_special_details          
;
;

_reflns_number_total             17989
_reflns_number_gt                10815
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1389
_refine_ls_R_factor_gt           0.0721
_refine_ls_wR_factor_gt          0.1548
_refine_ls_wR_factor_ref         0.1850
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_refine_ls_number_reflns         17989
_refine_ls_number_parameters     793
_refine_ls_number_restraints     1
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0567P)²+2.0365P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.889
_refine_diff_density_min         -0.810
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;

Flack x determined using 3336 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.47(6)

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'

_computing_data_collection       'APEX3 (Bruker AXS Inc., 2017)'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'XT, VERSION 2014/5'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  'APEX3 (Bruker AXS Inc., 2017)'

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
C C1 0.38447(15) 0.4857(11) 0.33621(18) 0.0209(12) Uani d . . . 1 . .
H H1 0.394961 0.365426 0.353899 0.025 Uiso calc U . R 1 . .
C C2 0.34708(15) 0.4584(12) 0.31777(19) 0.0266(14) Uani d . . . 1 . .
H H2 0.331894 0.318866 0.323412 0.032 Uiso calc U . R 1 . .
C C3 0.33272(15) 0.6321(11) 0.29183(18) 0.0243(13) Uani d . . . 1 . .
H H3 0.307829 0.611489 0.279163 0.029 Uiso calc U . R 1 . .
C C4 0.35434(16) 0.8366(12) 0.28412(19) 0.0271(13) Uani d . . . 1 . .
H H4 0.344121 0.957256 0.266325 0.032 Uiso calc U . R 1 . .
C C5 0.39102(15) 0.8682(11) 0.30215(18) 0.0236(12) Uani d . . . 1 . .
H H5 0.406033 1.008961 0.296912 0.028 Uiso calc U . R 1 . .
C C6 0.40485(14) 0.6909(10) 0.32765(17) 0.0179(11) Uani d . . . 1 . .
C C7 0.47460(14) 0.6948(10) 0.32799(16) 0.0167(11) Uani d . . . 1 . .
C C8 0.49869(14) 0.9457(10) 0.38482(18) 0.0199(12) Uani d . . . 1 . .
C C9 0.47776(15) 1.1582(11) 0.38194(18) 0.0210(12) Uani d . . . 1 . .
H H9 0.467598 1.209618 0.356088 0.025 Uiso calc U . R 1 . .
C C10 0.47174(15) 1.2957(11) 0.41720(19) 0.0239(13) Uani d . . . 1 . .
H H10 0.457215 1.441164 0.415347 0.029 Uiso calc U . R 1 . .
C C11 0.48661(15) 1.2235(11) 0.45503(19) 0.0264(13) Uani d . . . 1 . .
H H11 0.48227 1.317545 0.47911 0.032 Uiso calc U . R 1 . .
C C12 0.50782(15) 1.0128(12) 0.45706(19) 0.0268(13) Uani d . . . 1 . .
H H12 0.518257 0.962662 0.482861 0.032 Uiso calc U . R 1 . .
C C13 0.51434(15) 0.8710(11) 0.42202(18) 0.0219(12) Uani d . . . 1 . .
H H13 0.529183 0.726682 0.423775 0.026 Uiso calc U . R 1 . .
C C14 0.54405(14) 0.7914(10) 0.33140(17) 0.0180(11) Uani d . . . 1 . .
C C15 0.55640(15) 0.9766(11) 0.30669(19) 0.0233(13) Uani d . . . 1 . .
H H15 0.539091 1.105094 0.300211 0.028 Uiso calc U . R 1 . .
C C16 0.59437(16) 0.9757(11) 0.2911(2) 0.0264(13) Uani d . . . 1 . .
H H16 0.603181 1.101822 0.273622 0.032 Uiso calc U . R 1 . .
C C17 0.61914(16) 0.7880(12) 0.3016(2) 0.0274(14) Uani d . . . 1 . .
H H17 0.645181 0.787471 0.291221 0.033 Uiso calc U . R 1 . .
C C18 0.60695(16) 0.6006(12) 0.3268(2) 0.0278(14) Uani d . . . 1 . .
H H18 0.624388 0.473361 0.33367 0.033 Uiso calc U . R 1 . .
C C19 0.56850(15) 0.6019(11) 0.34205(19) 0.0235(13) Uani d . . . 1 . .
H H19 0.559376 0.475478 0.359312 0.028 Uiso calc U . R 1 . .
C C21 0.34201(15) 0.9300(10) 0.40302(18) 0.0210(12) Uani d . . . 1 . .
H H21 0.330844 1.050594 0.38587 0.025 Uiso calc U . R 1 . .
C C22 0.37957(15) 0.9580(11) 0.41966(19) 0.0245(13) Uani d . . . 1 . .
H H22 0.39407 1.100443 0.414175 0.029 Uiso calc U . R 1 . .
C C23 0.39564(15) 0.7796(12) 0.44400(19) 0.0247(13) Uani d . . . 1 . .
H H23 0.421278 0.799209 0.454931 0.03 Uiso calc U . R 1 . .
C C24 0.37472(15) 0.5730(12) 0.45257(19) 0.0260(14) Uani d . . . 1 . .
H H24 0.386016 0.451074 0.469345 0.031 Uiso calc U . R 1 . .
C C25 0.33680(15) 0.5424(10) 0.43657(18) 0.0201(12) Uani d . . . 1 . .
H H25 0.322012 0.401553 0.442399 0.024 Uiso calc U . R 1 . .
C C26 0.32171(13) 0.7230(10) 0.41218(17) 0.0174(11) Uani d . . . 1 . .
C C27 0.25160(14) 0.7199(10) 0.41294(17) 0.0160(11) Uani d . . . 1 . .
C C28 0.18197(14) 0.6602(10) 0.40651(17) 0.0167(11) Uani d . . . 1 . .
C C29 0.16679(15) 0.4845(11) 0.43223(17) 0.0209(12) Uani d . . . 1 . .
H H29 0.182156 0.349009 0.439855 0.025 Uiso calc U . R 1 . .
C C30 0.12835(15) 0.5099(11) 0.44683(18) 0.0237(13) Uani d . . . 1 . .
H H30 0.11743 0.392025 0.46469 0.028 Uiso calc U . R 1 . .
C C31 0.10643(15) 0.7076(12) 0.4351(2) 0.0260(14) Uani d . . . 1 . .
H H31 0.08047 0.725589 0.445236 0.031 Uiso calc U . R 1 . .
C C32 0.12174(15) 0.8798(11) 0.4087(2) 0.0259(13) Uani d . . . 1 . .
H H32 0.106131 1.012698 0.400337 0.031 Uiso calc U . R 1 . .
C C33 0.16034(15) 0.8573(11) 0.39444(19) 0.0230(12) Uani d . . . 1 . .
H H33 0.171383 0.975859 0.376777 0.028 Uiso calc U . R 1 . .
C C34 0.22787(13) 0.4814(10) 0.35536(17) 0.0157(10) Uani d . . . 1 . .
C C35 0.21422(15) 0.5556(10) 0.31692(18) 0.0192(12) Uani d . . . 1 . .
H H35 0.200331 0.702937 0.314219 0.023 Uiso calc U . R 1 . .
C C36 0.22108(15) 0.4124(11) 0.2826(2) 0.0240(13) Uani d . . . 1 . .
H H36 0.211512 0.460816 0.256306 0.029 Uiso calc U . R 1 . .
C C37 0.24198(15) 0.1974(11) 0.28643(19) 0.0216(12) Uani d . . . 1 . .
H H37 0.24768 0.103134 0.262695 0.026 Uiso calc U . R 1 . .
C C38 0.25417(14) 0.1237(10) 0.32458(18) 0.0195(11) Uani d . . . 1 . .
H H38 0.267221 -0.026488 0.327295 0.023 Uiso calc U . R 1 . .
C C39 0.24790(13) 0.2630(10) 0.35927(17) 0.0160(11) Uani d . . . 1 . .
H H39 0.257095 0.211118 0.385488 0.019 Uiso calc U . R 1 . .
C C40 0.40165(15) 0.5296(11) 0.69787(19) 0.0252(13) Uani d . . . 1 . .
H H40 0.384641 0.398978 0.703993 0.03 Uiso calc U . R 1 . .
C C41 0.43832(16) 0.5473(11) 0.71640(19) 0.0266(14) Uani d . . . 1 . .
H H41 0.446788 0.426364 0.735131 0.032 Uiso calc U . R 1 . .
C C42 0.46264(15) 0.7418(11) 0.7076(2) 0.0250(12) Uani d . . . 1 . .
H H42 0.487548 0.754325 0.7205 0.03 Uiso calc U . R 1 . .
C C43 0.45065(16) 0.9160(12) 0.68013(19) 0.0258(14) Uani d . . . 1 . .
H H43 0.467594 1.046376 0.673662 0.031 Uiso calc U . R 1 . .
C C44 0.41372(15) 0.9020(11) 0.66174(18) 0.0234(13) Uani d . . . 1 . .
H H44 0.404752 1.024838 0.643644 0.028 Uiso calc U . R 1 . .
C C45 0.39072(14) 0.7057(11) 0.67053(18) 0.0204(12) Uani d . . . 1 . .
C C46 0.32052(14) 0.7284(10) 0.66508(16) 0.0161(11) Uani d . . . 1 . .
C C47 0.25105(14) 0.6777(10) 0.65117(17) 0.0165(11) Uani d . . . 1 . .
C C48 0.23186(15) 0.5061(11) 0.67409(18) 0.0232(12) Uani d . . . 1 . .
H H48 0.245208 0.365482 0.683106 0.028 Uiso calc U . R 1 . .
C C49 0.19226(16) 0.5417(12) 0.68396(19) 0.0261(13) Uani d . . . 1 . .
H H49 0.178739 0.427831 0.700574 0.031 Uiso calc U . R 1 . .
C C50 0.17303(15) 0.7431(11) 0.66940(19) 0.0255(14) Uani d . . . 1 . .
H H50 0.146052 0.765369 0.675593 0.031 Uiso calc U . R 1 . .
C C51 0.19253(15) 0.9129(11) 0.6459(2) 0.0271(14) Uani d . . . 1 . .
H H51 0.178944 1.050859 0.636141 0.032 Uiso calc U . R 1 . .
C C52 0.23214(15) 0.8820(11) 0.63653(19) 0.0242(13) Uani d . . . 1 . .
H H52 0.245844 0.997954 0.620519 0.029 Uiso calc U . R 1 . .
C C53 0.29936(13) 0.4852(10) 0.60549(17) 0.0164(11) Uani d . . . 1 . .
C C54 0.28535(14) 0.5485(11) 0.56697(18) 0.0206(12) Uani d . . . 1 . .
H H54 0.271088 0.694022 0.563574 0.025 Uiso calc U . R 1 . .
C C55 0.29202(15) 0.4006(11) 0.53332(18) 0.0227(13) Uani d . . . 1 . .
H H55 0.282661 0.446672 0.506843 0.027 Uiso calc U . R 1 . .
C C56 0.31194(14) 0.1890(11) 0.53784(18) 0.0216(12) Uani d . . . 1 . .
H H56 0.316138 0.087765 0.514613 0.026 Uiso calc U . R 1 . .
C C57 0.32626(15) 0.1210(11) 0.57690(19) 0.0226(12) Uani d . . . 1 . .
H H57 0.340345 -0.025338 0.580105 0.027 Uiso calc U . R 1 . .
C C58 0.31964(14) 0.2698(10) 0.61084(18) 0.0206(12) Uani d . . . 1 . .
H H58 0.32889 0.224781 0.637419 0.025 Uiso calc U . R 1 . .
C C59 0.45811(15) 0.4438(11) 0.59267(19) 0.0248(13) Uani d . . . 1 . .
H H59 0.469525 0.319287 0.608795 0.03 Uiso calc U . R 1 . .
C C60 0.41979(15) 0.4288(12) 0.5797(2) 0.0259(14) Uani d . . . 1 . .
H H60 0.404698 0.291027 0.586724 0.031 Uiso calc U . R 1 . .
C C61 0.40292(16) 0.6100(12) 0.55672(19) 0.0275(14) Uani d . . . 1 . .
H H61 0.376359 0.597311 0.54818 0.033 Uiso calc U . R 1 . .
C C62 0.42476(15) 0.8104(12) 0.54612(18) 0.0248(13) Uani d . . . 1 . .
H H62 0.413078 0.934759 0.530181 0.03 Uiso calc U . R 1 . .
C C63 0.46340(16) 0.8318(11) 0.55847(17) 0.0216(12) Uani d . . . 1 . .
H H63 0.478543 0.969392 0.551452 0.026 Uiso calc U . R 1 . .
C C64 0.47939(14) 0.6430(11) 0.58173(17) 0.0204(12) Uani d . . . 1 . .
C C65 0.54869(14) 0.6588(10) 0.57140(17) 0.0180(11) Uani d . . . 1 . .
C C66 0.57592(15) 0.8887(10) 0.62790(18) 0.0194(12) Uani d . . . 1 . .
C C67 0.59109(15) 0.7782(11) 0.66296(19) 0.0238(12) Uani d . . . 1 . .
H H67 0.60499 0.630551 0.660743 0.029 Uiso calc U . R 1 . .
C C68 0.58571(16) 0.8857(12) 0.70123(19) 0.0272(13) Uani d . . . 1 . .
H H68 0.596072 0.811139 0.725273 0.033 Uiso calc U . R 1 . .
C C69 0.56538(15) 1.1009(12) 0.7047(2) 0.0279(13) Uani d . . . 1 . .
H H69 0.561221 1.171684 0.731084 0.033 Uiso calc U . R 1 . .
C C70 0.55119(16) 1.2115(12) 0.6694(2) 0.0270(13) Uani d . . . 1 . .
H H70 0.537776 1.360718 0.671787 0.032 Uiso calc U . R 1 . .
C C71 0.55617(15) 1.1087(11) 0.63058(19) 0.0235(13) Uani d . . . 1 . .
H H71 0.546403 1.186041 0.606518 0.028 Uiso calc U . R 1 . .
C C72 0.61728(14) 0.7744(10) 0.56807(17) 0.0175(11) Uani d . . . 1 . .
C C73 0.62635(15) 0.9670(11) 0.54311(18) 0.0215(12) Uani d . . . 1 . .
H H73 0.607888 1.092026 0.538411 0.026 Uiso calc U . R 1 . .
C C74 0.66361(15) 0.9737(11) 0.5248(2) 0.0261(13) Uani d . . . 1 . .
H H74 0.670331 1.102973 0.506905 0.031 Uiso calc U . R 1 . .
C C75 0.69038(15) 0.7952(11) 0.53241(18) 0.0231(13) Uani d . . . 1 . .
H H75 0.715841 0.804499 0.520634 0.028 Uiso calc U . R 1 . .
C C76 0.68056(15) 0.6028(11) 0.55704(19) 0.0237(13) Uani d . . . 1 . .
H H76 0.69906 0.477798 0.561586 0.028 Uiso calc U . R 1 . .
C C77 0.64333(15) 0.5899(11) 0.57554(18) 0.0212(12) Uani d . . . 1 . .
H H77 0.636341 0.457836 0.592676 0.025 Uiso calc U . R 1 . .
N N1 0.50464(12) 0.7992(9) 0.34807(14) 0.0195(10) Uani d . . . 1 . .
N N2 0.22176(11) 0.6307(8) 0.39132(14) 0.0161(9) Uani d . . . 1 . .
N N3 0.29203(12) 0.6388(8) 0.64081(14) 0.0184(10) Uani d . . . 1 . .
N N4 0.57923(11) 0.7706(8) 0.58838(14) 0.0178(10) Uani d . . . 1 . .
O O1 0.44062(9) 0.7286(7) 0.34885(12) 0.0203(9) Uani d . . . 1 . .
O O2 0.28569(9) 0.6827(7) 0.39214(11) 0.0183(8) Uani d . . . 1 . .
O O3 0.35585(10) 0.6777(7) 0.64779(12) 0.0215(9) Uani d . . . 1 . .
O O4 0.51739(10) 0.6726(8) 0.59750(12) 0.0227(9) Uani d . . . 1 . .
S S1 0.47841(4) 0.5337(3) 0.28511(4) 0.0223(3) Uani d . . . 1 . .
S S2 0.24903(4) 0.8663(3) 0.45748(5) 0.0197(3) Uani d . . . 1 . .
S S3 0.31442(4) 0.8847(3) 0.70770(5) 0.0227(3) Uani d . . . 1 . .
S S4 0.54796(4) 0.5177(3) 0.52668(5) 0.0235(3) Uani d . . . 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
C1 C6 . 1.364(8) ?
C1 C2 . 1.417(8) ?
C1 H1 . 0.95 ?
C2 C3 . 1.370(9) ?
C2 H2 . 0.95 ?
C3 C4 . 1.378(8) ?
C3 H3 . 0.95 ?
C4 C5 . 1.392(8) ?
C4 H4 . 0.95 ?
C5 C6 . 1.369(8) ?
C5 H5 . 0.95 ?
C6 O1 . 1.416(6) ?
C7 N1 . 1.345(7) ?
C7 O1 . 1.355(6) ?
C7 S1 . 1.657(6) ?
C8 C13 . 1.381(8) ?
C8 C9 . 1.383(8) ?
C8 N1 . 1.456(7) ?
C9 C10 . 1.389(8) ?
C9 H9 . 0.95 ?
C10 C11 . 1.385(9) ?
C10 H10 . 0.95 ?
C11 C12 . 1.378(8) ?
C11 H11 . 0.95 ?
C12 C13 . 1.399(9) ?
C12 H12 . 0.95 ?
C13 H13 . 0.95 ?
C14 C15 . 1.370(8) ?
C14 C19 . 1.387(8) ?
C14 N1 . 1.449(6) ?
C15 C16 . 1.390(8) ?
C15 H15 . 0.95 ?
C16 C17 . 1.384(8) ?
C16 H16 . 0.95 ?
C17 C18 . 1.387(9) ?
C17 H17 . 0.95 ?
C18 C19 . 1.401(8) ?
C18 H18 . 0.95 ?
C19 H19 . 0.95 ?
C21 C26 . 1.375(8) ?
C21 C22 . 1.399(7) ?
C21 H21 . 0.95 ?
C22 C23 . 1.380(9) ?
C22 H22 . 0.95 ?
C23 C24 . 1.380(9) ?
C23 H23 . 0.95 ?
C24 C25 . 1.404(7) ?
C24 H24 . 0.95 ?
C25 C26 . 1.376(8) ?
C25 H25 . 0.95 ?
C26 O2 . 1.408(6) ?
C27 N2 . 1.331(6) ?
C27 O2 . 1.360(6) ?
C27 S2 . 1.658(6) ?
C28 C33 . 1.377(8) ?
C28 C29 . 1.384(8) ?
C28 N2 . 1.453(6) ?
C29 C30 . 1.401(7) ?
C29 H29 . 0.95 ?
C30 C31 . 1.382(8) ?
C30 H30 . 0.95 ?
C31 C32 . 1.384(9) ?
C31 H31 . 0.95 ?
C32 C33 . 1.402(7) ?
C32 H32 . 0.95 ?
C33 H33 . 0.95 ?
C34 C35 . 1.391(8) ?
C34 C39 . 1.398(7) ?
C34 N2 . 1.445(7) ?
C35 C36 . 1.387(8) ?
C35 H35 . 0.95 ?
C36 C37 . 1.397(8) ?
C36 H36 . 0.95 ?
C37 C38 . 1.366(8) ?
C37 H37 . 0.95 ?
C38 C39 . 1.381(8) ?
C38 H38 . 0.95 ?
C39 H39 . 0.95 ?
C40 C45 . 1.371(8) ?
C40 C41 . 1.391(7) ?
C40 H40 . 0.95 ?
C41 C42 . 1.392(8) ?
C41 H41 . 0.95 ?
C42 C43 . 1.376(8) ?
C42 H42 . 0.95 ?
C43 C44 . 1.396(7) ?
C43 H43 . 0.95 ?
C44 C45 . 1.374(8) ?
C44 H44 . 0.95 ?
C45 O3 . 1.408(6) ?
C46 N3 . 1.345(7) ?
C46 O3 . 1.358(6) ?
C46 S3 . 1.644(5) ?
C47 C48 . 1.374(8) ?
C47 C52 . 1.389(8) ?
C47 N3 . 1.454(6) ?
C48 C49 . 1.403(7) ?
C48 H48 . 0.95 ?
C49 C50 . 1.380(9) ?
C49 H49 . 0.95 ?
C50 C51 . 1.382(9) ?
C50 H50 . 0.95 ?
C51 C52 . 1.396(7) ?
C51 H51 . 0.95 ?
C52 H52 . 0.95 ?
C53 C54 . 1.381(8) ?
C53 C58 . 1.393(8) ?
C53 N3 . 1.449(7) ?
C54 C55 . 1.383(8) ?
C54 H54 . 0.95 ?
C55 C56 . 1.366(8) ?
C55 H55 . 0.95 ?
C56 C57 . 1.407(8) ?
C56 H56 . 0.95 ?
C57 C58 . 1.394(8) ?
C57 H57 . 0.95 ?
C58 H58 . 0.95 ?
C59 C64 . 1.370(8) ?
C59 C60 . 1.376(7) ?
C59 H59 . 0.95 ?
C60 C61 . 1.378(9) ?
C60 H60 . 0.95 ?
C61 C62 . 1.383(9) ?
C61 H61 . 0.95 ?
C62 C63 . 1.383(8) ?
C62 H62 . 0.95 ?
C63 C64 . 1.402(8) ?
C63 H63 . 0.95 ?
C64 O4 . 1.403(6) ?
C65 N4 . 1.332(6) ?
C65 O4 . 1.364(6) ?
C65 S4 . 1.647(6) ?
C66 C67 . 1.391(8) ?
C66 C71 . 1.398(8) ?
C66 N4 . 1.442(7) ?
C67 C68 . 1.388(8) ?
C67 H67 . 0.95 ?
C68 C69 . 1.387(8) ?
C68 H68 . 0.95 ?
C69 C70 . 1.385(9) ?
C69 H69 . 0.95 ?
C70 C71 . 1.392(8) ?
C70 H70 . 0.95 ?
C71 H71 . 0.95 ?
C72 C73 . 1.376(8) ?
C72 C77 . 1.378(7) ?
C72 N4 . 1.455(6) ?
C73 C74 . 1.404(7) ?
C73 H73 . 0.95 ?
C74 C75 . 1.370(8) ?
C74 H74 . 0.95 ?
C75 C76 . 1.375(8) ?
C75 H75 . 0.95 ?
C76 C77 . 1.407(7) ?
C76 H76 . 0.95 ?
C77 H77 . 0.95 ?

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
C6 C1 C2 . . 117.6(6) ?
C6 C1 H1 . . 121.2 ?
C2 C1 H1 . . 121.2 ?
C3 C2 C1 . . 120.3(5) ?
C3 C2 H2 . . 119.8 ?
C1 C2 H2 . . 119.8 ?
C2 C3 C4 . . 120.0(5) ?
C2 C3 H3 . . 120.0 ?
C4 C3 H3 . . 120.0 ?
C3 C4 C5 . . 120.6(6) ?
C3 C4 H4 . . 119.7 ?
C5 C4 H4 . . 119.7 ?
C6 C5 C4 . . 118.2(6) ?
C6 C5 H5 . . 120.9 ?
C4 C5 H5 . . 120.9 ?
C1 C6 C5 . . 123.2(5) ?
C1 C6 O1 . . 117.7(5) ?
C5 C6 O1 . . 118.9(5) ?
N1 C7 O1 . . 110.6(4) ?
N1 C7 S1 . . 125.3(4) ?
O1 C7 S1 . . 124.0(4) ?
C13 C8 C9 . . 121.0(6) ?
C13 C8 N1 . . 119.4(5) ?
C9 C8 N1 . . 119.6(5) ?
C8 C9 C10 . . 119.4(5) ?
C8 C9 H9 . . 120.3 ?
C10 C9 H9 . . 120.3 ?
C11 C10 C9 . . 120.9(6) ?
C11 C10 H10 . . 119.5 ?
C9 C10 H10 . . 119.5 ?
C12 C11 C10 . . 118.7(6) ?
C12 C11 H11 . . 120.6 ?
C10 C11 H11 . . 120.6 ?
C11 C12 C13 . . 121.6(6) ?
C11 C12 H12 . . 119.2 ?
C13 C12 H12 . . 119.2 ?
C8 C13 C12 . . 118.4(6) ?
C8 C13 H13 . . 120.8 ?
C12 C13 H13 . . 120.8 ?
C15 C14 C19 . . 122.0(5) ?
C15 C14 N1 . . 118.7(5) ?
C19 C14 N1 . . 119.2(5) ?
C14 C15 C16 . . 119.7(5) ?
C14 C15 H15 . . 120.1 ?
C16 C15 H15 . . 120.1 ?
C17 C16 C15 . . 118.9(6) ?
C17 C16 H16 . . 120.6 ?
C15 C16 H16 . . 120.6 ?
C16 C17 C18 . . 121.8(5) ?
C16 C17 H17 . . 119.1 ?
C18 C17 H17 . . 119.1 ?
C17 C18 C19 . . 118.9(6) ?
C17 C18 H18 . . 120.5 ?
C19 C18 H18 . . 120.5 ?
C14 C19 C18 . . 118.7(6) ?
C14 C19 H19 . . 120.7 ?
C18 C19 H19 . . 120.7 ?
C26 C21 C22 . . 118.1(5) ?
C26 C21 H21 . . 120.9 ?
C22 C21 H21 . . 120.9 ?
C23 C22 C21 . . 120.3(5) ?
C23 C22 H22 . . 119.9 ?
C21 C22 H22 . . 119.9 ?
C24 C23 C22 . . 120.5(5) ?
C24 C23 H23 . . 119.8 ?
C22 C23 H23 . . 119.8 ?
C23 C24 C25 . . 120.2(5) ?
C23 C24 H24 . . 119.9 ?
C25 C24 H24 . . 119.9 ?
C26 C25 C24 . . 117.9(5) ?
C26 C25 H25 . . 121.0 ?
C24 C25 H25 . . 121.0 ?
C21 C26 C25 . . 123.0(5) ?
C21 C26 O2 . . 118.2(5) ?
C25 C26 O2 . . 118.4(5) ?
N2 C27 O2 . . 109.7(5) ?
N2 C27 S2 . . 126.8(4) ?
O2 C27 S2 . . 123.4(4) ?
C33 C28 C29 . . 122.1(5) ?
C33 C28 N2 . . 119.6(5) ?
C29 C28 N2 . . 118.3(5) ?
C28 C29 C30 . . 118.8(5) ?
C28 C29 H29 . . 120.6 ?
C30 C29 H29 . . 120.6 ?
C31 C30 C29 . . 119.6(5) ?
C31 C30 H30 . . 120.2 ?
C29 C30 H30 . . 120.2 ?
C30 C31 C32 . . 121.0(5) ?
C30 C31 H31 . . 119.5 ?
C32 C31 H31 . . 119.5 ?
C31 C32 C33 . . 119.8(5) ?
C31 C32 H32 . . 120.1 ?
C33 C32 H32 . . 120.1 ?
C28 C33 C32 . . 118.7(5) ?
C28 C33 H33 . . 120.6 ?
C32 C33 H33 . . 120.6 ?
C35 C34 C39 . . 120.1(5) ?
C35 C34 N2 . . 120.2(5) ?
C39 C34 N2 . . 119.7(5) ?
C36 C35 C34 . . 119.4(5) ?
C36 C35 H35 . . 120.3 ?
C34 C35 H35 . . 120.3 ?
C35 C36 C37 . . 120.3(6) ?
C35 C36 H36 . . 119.8 ?
C37 C36 H36 . . 119.8 ?
C38 C37 C36 . . 119.5(5) ?
C38 C37 H37 . . 120.3 ?
C36 C37 H37 . . 120.3 ?
C37 C38 C39 . . 121.4(5) ?
C37 C38 H38 . . 119.3 ?
C39 C38 H38 . . 119.3 ?
C38 C39 C34 . . 119.2(5) ?
C38 C39 H39 . . 120.4 ?
C34 C39 H39 . . 120.4 ?
C45 C40 C41 . . 118.2(5) ?
C45 C40 H40 . . 120.9 ?
C41 C40 H40 . . 120.9 ?
C40 C41 C42 . . 120.2(6) ?
C40 C41 H41 . . 119.9 ?
C42 C41 H41 . . 119.9 ?
C43 C42 C41 . . 120.1(5) ?
C43 C42 H42 . . 120.0 ?
C41 C42 H42 . . 120.0 ?
C42 C43 C44 . . 120.3(5) ?
C42 C43 H43 . . 119.8 ?
C44 C43 H43 . . 119.8 ?
C45 C44 C43 . . 118.1(5) ?
C45 C44 H44 . . 120.9 ?
C43 C44 H44 . . 120.9 ?
C40 C45 C44 . . 123.0(5) ?
C40 C45 O3 . . 119.3(5) ?
C44 C45 O3 . . 117.5(5) ?
N3 C46 O3 . . 108.9(4) ?
N3 C46 S3 . . 126.5(4) ?
O3 C46 S3 . . 124.6(4) ?
C48 C47 C52 . . 122.0(5) ?
C48 C47 N3 . . 118.7(5) ?
C52 C47 N3 . . 119.3(5) ?
C47 C48 C49 . . 118.9(6) ?
C47 C48 H48 . . 120.5 ?
C49 C48 H48 . . 120.5 ?
C50 C49 C48 . . 119.7(6) ?
C50 C49 H49 . . 120.2 ?
C48 C49 H49 . . 120.2 ?
C49 C50 C51 . . 120.8(5) ?
C49 C50 H50 . . 119.6 ?
C51 C50 H50 . . 119.6 ?
C50 C51 C52 . . 120.1(6) ?
C50 C51 H51 . . 119.9 ?
C52 C51 H51 . . 119.9 ?
C47 C52 C51 . . 118.4(6) ?
C47 C52 H52 . . 120.8 ?
C51 C52 H52 . . 120.8 ?
C54 C53 C58 . . 120.2(5) ?
C54 C53 N3 . . 120.2(5) ?
C58 C53 N3 . . 119.6(5) ?
C53 C54 C55 . . 120.2(5) ?
C53 C54 H54 . . 119.9 ?
C55 C54 H54 . . 119.9 ?
C56 C55 C54 . . 120.6(5) ?
C56 C55 H55 . . 119.7 ?
C54 C55 H55 . . 119.7 ?
C55 C56 C57 . . 120.0(5) ?
C55 C56 H56 . . 120.0 ?
C57 C56 H56 . . 120.0 ?
C58 C57 C56 . . 119.5(5) ?
C58 C57 H57 . . 120.2 ?
C56 C57 H57 . . 120.2 ?
C53 C58 C57 . . 119.5(5) ?
C53 C58 H58 . . 120.3 ?
C57 C58 H58 . . 120.3 ?
C64 C59 C60 . . 118.3(6) ?
C64 C59 H59 . . 120.9 ?
C60 C59 H59 . . 120.9 ?
C59 C60 C61 . . 121.2(6) ?
C59 C60 H60 . . 119.4 ?
C61 C60 H60 . . 119.4 ?
C60 C61 C62 . . 119.8(5) ?
C60 C61 H61 . . 120.1 ?
C62 C61 H61 . . 120.1 ?
C63 C62 C61 . . 120.8(6) ?
C63 C62 H62 . . 119.6 ?
C61 C62 H62 . . 119.6 ?
C62 C63 C64 . . 117.5(6) ?
C62 C63 H63 . . 121.3 ?
C64 C63 H63 . . 121.2 ?
C59 C64 C63 . . 122.5(5) ?
C59 C64 O4 . . 119.4(5) ?
C63 C64 O4 . . 117.9(5) ?
N4 C65 O4 . . 109.3(5) ?
N4 C65 S4 . . 126.6(4) ?
O4 C65 S4 . . 124.0(4) ?
C67 C66 C71 . . 121.0(5) ?
C67 C66 N4 . . 119.6(5) ?
C71 C66 N4 . . 119.4(5) ?
C68 C67 C66 . . 119.3(6) ?
C68 C67 H67 . . 120.3 ?
C66 C67 H67 . . 120.3 ?
C69 C68 C67 . . 120.7(6) ?
C69 C68 H68 . . 119.7 ?
C67 C68 H68 . . 119.7 ?
C70 C69 C68 . . 119.3(6) ?
C70 C69 H69 . . 120.3 ?
C68 C69 H69 . . 120.3 ?
C69 C70 C71 . . 121.4(6) ?
C69 C70 H70 . . 119.3 ?
C71 C70 H70 . . 119.3 ?
C70 C71 C66 . . 118.3(6) ?
C70 C71 H71 . . 120.9 ?
C66 C71 H71 . . 120.9 ?
C73 C72 C77 . . 122.4(5) ?
C73 C72 N4 . . 118.5(5) ?
C77 C72 N4 . . 119.0(5) ?
C72 C73 C74 . . 118.2(5) ?
C72 C73 H73 . . 120.9 ?
C74 C73 H73 . . 120.9 ?
C75 C74 C73 . . 120.5(6) ?
C75 C74 H74 . . 119.7 ?
C73 C74 H74 . . 119.7 ?
C74 C75 C76 . . 120.3(5) ?
C74 C75 H75 . . 119.8 ?
C76 C75 H75 . . 119.8 ?
C75 C76 C77 . . 120.5(5) ?
C75 C76 H76 . . 119.8 ?
C77 C76 H76 . . 119.8 ?
C72 C77 C76 . . 118.0(5) ?
C72 C77 H77 . . 121.0 ?
C76 C77 H77 . . 121.0 ?
C7 N1 C14 . . 120.9(4) ?
C7 N1 C8 . . 122.0(4) ?
C14 N1 C8 . . 116.8(4) ?
C27 N2 C34 . . 121.8(4) ?
C27 N2 C28 . . 119.6(4) ?
C34 N2 C28 . . 118.2(4) ?
C46 N3 C53 . . 123.7(4) ?
C46 N3 C47 . . 120.3(4) ?
C53 N3 C47 . . 115.8(4) ?
C65 N4 C66 . . 121.2(4) ?
C65 N4 C72 . . 121.2(4) ?
C66 N4 C72 . . 117.6(4) ?
C7 O1 C6 . . 118.4(4) ?
C27 O2 C26 . . 119.6(4) ?
C46 O3 C45 . . 120.7(4) ?
C65 O4 C64 . . 119.5(4) ?

####################################################################### 
# 
# 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_fg834m
_database_code_depnum_ccdc_archive 'CCDC 1831305'
loop_
_audit_author_name
_audit_author_address
'Rakesh Ganguly'
;Nanyang Technological University
Singapore
;
_audit_update_record             
;
2018-03-21 deposited with the CCDC.	2020-10-30 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H13 N O S'
_chemical_formula_iupac          ?
_chemical_formula_weight         231.30
_chemical_absolute_configuration ?

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 c 1'
_space_group_name_Hall           'P -2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'

_cell_length_a                   11.9751(10)
_cell_length_b                   5.8514(5)
_cell_length_c                   8.4304(6)
_cell_angle_alpha                90
_cell_angle_beta                 103.293(3)
_cell_angle_gamma                90
_cell_volume                     574.90(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2858
_cell_measurement_theta_min      3.4818
_cell_measurement_theta_max      33.2346
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.060
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             244

_exptl_absorpt_coefficient_mu    0.258
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.33
_exptl_absorpt_correction_T_max  0.98

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'Incoatec microfocus source'
_diffrn_source_type              'Bruker D8 Quest'

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'Multilayer Mirror'

_diffrn_measurement_device_type  'Photon II CPADs detector'
_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 7.4074

_diffrn_reflns_number            8996
_diffrn_reflns_av_R_equivalents  0.0973
_diffrn_reflns_av_unetI/netI     0.1417
_diffrn_reflns_theta_min         3.48
_diffrn_reflns_theta_max         35.04
_diffrn_reflns_theta_full        35.04
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13

_refine_special_details          
;

Refined as a 2-component inversion twin.
;

_reflns_number_total             4562
_reflns_number_gt                3303
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1215
_refine_ls_R_factor_gt           0.0936
_refine_ls_wR_factor_gt          0.2256
_refine_ls_wR_factor_ref         0.2591
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.016
_refine_ls_number_reflns         4562
_refine_ls_number_parameters     148
_refine_ls_number_restraints     2
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1498P)²] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         1.452
_refine_diff_density_min         -1.486
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;

Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.1(2)

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'

_computing_data_collection       'APEX3 (Bruker AXS Inc., 2017)'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'XT, VERSION 2014/5'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  'APEX3 (Bruker AXS Inc., 2017)'

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
C C1 0.4477(4) 0.5567(8) 0.5947(5) 0.0162(8) Uani d . . . 1 . .
H H1 0.489943 0.457746 0.676028 0.019 Uiso calc U . R 1 . .
C C2 0.3377(4) 0.5024(8) 0.5135(6) 0.0162(8) Uani d . . . 1 . .
H H2 0.304074 0.363876 0.538486 0.019 Uiso calc U . R 1 . .
C C3 0.2739(4) 0.6502(8) 0.3932(5) 0.0150(7) Uani d . . . 1 . .
C C4 0.1593(4) 0.5997(9) 0.3114(6) 0.0181(8) Uani d . . . 1 . .
H H4 0.12459 0.461562 0.334902 0.022 Uiso calc U . R 1 . .
C C5 0.0981(4) 0.7492(9) 0.1985(6) 0.0196(9) Uani d . . . 1 . .
H H5 0.021218 0.713883 0.144989 0.024 Uiso calc U . R 1 . .
C C6 0.1482(4) 0.9550(9) 0.1610(6) 0.0202(9) Uani d . . . 1 . .
H H6 0.105563 1.056009 0.081509 0.024 Uiso calc U . R 1 . .
C C7 0.2584(4) 1.0085(7) 0.2397(6) 0.0161(8) Uani d . . . 1 . .
H H7 0.291444 1.147725 0.214826 0.019 Uiso calc U . R 1 . .
C C8 0.3240(4) 0.8586(8) 0.3578(5) 0.0148(7) Uani d . . . 1 . .
C C9 0.4380(4) 0.9114(8) 0.4410(5) 0.0150(7) Uani d . . . 1 . .
H H9 0.473276 1.04893 0.417641 0.018 Uiso calc U . R 1 . .
C C10 0.4966(4) 0.7623(8) 0.5550(5) 0.0156(7) Uani d . . . 1 . .
C C11 0.6991(4) 0.7135(8) 0.6396(5) 0.0150(7) Uani d . . . 1 . .
C C12 0.9026(4) 0.7025(9) 0.7567(6) 0.0226(9) Uani d . . . 1 . .
H H12A 0.906232 0.564647 0.823703 0.034 Uiso calc U . R 1 . .
H H12B 0.961993 0.810375 0.810232 0.034 Uiso calc U . R 1 . .
H H12C 0.915272 0.661302 0.649516 0.034 Uiso calc U . R 1 . .
C C13 0.7821(5) 1.0060(8) 0.8400(7) 0.0220(10) Uani d . . . 1 . .
H H13A 0.7208 1.10751 0.783021 0.033 Uiso calc U . R 1 . .
H H13B 0.855184 1.088824 0.863723 0.033 Uiso calc U . R 1 . .
H H13C 0.764815 0.953978 0.94223 0.033 Uiso calc U . R 1 . .
N N1 0.7903(3) 0.8080(7) 0.7368(5) 0.0169(7) Uani d . . . 1 . .
O O1 0.6031(3) 0.8335(6) 0.6461(4) 0.0167(6) Uani d . . . 1 . .
S S1 0.70054(14) 0.4877(2) 0.52109(18) 0.0202(3) Uani d . . . 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
C1 C2 . 1.374(7) ?
C1 C10 . 1.412(7) ?
C1 H1 . 0.95 ?
C2 C3 . 1.416(6) ?
C2 H2 . 0.95 ?
C3 C4 . 1.419(6) ?
C3 C8 . 1.421(6) ?
C4 C5 . 1.374(7) ?
C4 H4 . 0.95 ?
C5 C6 . 1.413(7) ?
C5 H5 . 0.95 ?
C6 C7 . 1.370(7) ?
C6 H6 . 0.95 ?
C7 C8 . 1.420(6) ?
C7 H7 . 0.95 ?
C8 C9 . 1.418(6) ?
C9 C10 . 1.367(6) ?
C9 H9 . 0.95 ?
C10 O1 . 1.393(5) ?
C11 N1 . 1.327(6) ?
C11 O1 . 1.358(5) ?
C11 S1 . 1.659(5) ?
C12 N1 . 1.454(6) ?
C12 H12A . 0.98 ?
C12 H12B . 0.98 ?
C12 H12C . 0.98 ?
C13 N1 . 1.465(7) ?
C13 H13A . 0.98 ?
C13 H13B . 0.98 ?
C13 H13C . 0.98 ?

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
C2 C1 C10 . . 118.8(4) ?
C2 C1 H1 . . 120.6 ?
C10 C1 H1 . . 120.6 ?
C1 C2 C3 . . 120.8(4) ?
C1 C2 H2 . . 119.6 ?
C3 C2 H2 . . 119.6 ?
C2 C3 C4 . . 121.6(4) ?
C2 C3 C8 . . 119.4(4) ?
C4 C3 C8 . . 119.0(4) ?
C5 C4 C3 . . 120.4(4) ?
C5 C4 H4 . . 119.8 ?
C3 C4 H4 . . 119.8 ?
C4 C5 C6 . . 120.7(4) ?
C4 C5 H5 . . 119.6 ?
C6 C5 H5 . . 119.6 ?
C7 C6 C5 . . 119.9(4) ?
C7 C6 H6 . . 120.1 ?
C5 C6 H6 . . 120.1 ?
C6 C7 C8 . . 120.9(4) ?
C6 C7 H7 . . 119.5 ?
C8 C7 H7 . . 119.5 ?
C9 C8 C7 . . 121.8(4) ?
C9 C8 C3 . . 119.2(4) ?
C7 C8 C3 . . 119.0(4) ?
C10 C9 C8 . . 119.3(4) ?
C10 C9 H9 . . 120.4 ?
C8 C9 H9 . . 120.4 ?
C9 C10 O1 . . 117.0(4) ?
C9 C10 C1 . . 122.5(4) ?
O1 C10 C1 . . 120.1(4) ?
N1 C11 O1 . . 110.1(4) ?
N1 C11 S1 . . 125.6(3) ?
O1 C11 S1 . . 124.2(3) ?
N1 C12 H12A . . 109.5 ?
N1 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
N1 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
N1 C13 H13A . . 109.5 ?
N1 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
N1 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?
C11 N1 C12 . . 120.2(4) ?
C11 N1 C13 . . 122.5(4) ?
C12 N1 C13 . . 117.0(4) ?
C11 O1 C10 . . 119.9(4) ?

####################################################################### 
# 
# 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_fg755m
_database_code_depnum_ccdc_archive 'CCDC 1831302'
loop_
_audit_author_name
_audit_author_address
'Rakesh Ganguly'
;Nanyang Technological University
Singapore
;
_audit_update_record             
;
2018-03-21 deposited with the CCDC.	2020-10-30 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H10 F N O S'
_chemical_formula_iupac          ?
_chemical_formula_weight         199.24

_chemical_melting_point          ?

_space_group_crystal_system      triclinic
_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                   7.3327(6)
_cell_length_b                   10.8014(9)
_cell_length_c                   12.9437(11)
_cell_angle_alpha                88.123(3)
_cell_angle_beta                 86.737(3)
_cell_angle_gamma                76.071(3)
_cell_volume                     993.23(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9950
_cell_measurement_theta_min      2.4780
_cell_measurement_theta_max      29.0112
_cell_measurement_temperature    301.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             416

_exptl_absorpt_coefficient_mu    0.300
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.88
_exptl_absorpt_correction_T_max  0.97

_exptl_special_details           
;
;

_diffrn_ambient_temperature      301.(2)

_diffrn_source                   'Incoatec microfocus source'
_diffrn_source_type              'Bruker D8 Quest'

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'Multilayer Mirror'

_diffrn_measurement_device_type  'Photon II CPADs detector'
_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 7.4074

_diffrn_reflns_number            32212
_diffrn_reflns_av_R_equivalents  0.0364
_diffrn_reflns_av_unetI/netI     0.0252
_diffrn_reflns_theta_min         2.48
_diffrn_reflns_theta_max         29.10
_diffrn_reflns_theta_full        29.10
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17

_refine_special_details          
;
;

_reflns_number_total             5258
_reflns_number_gt                3768
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0733
_refine_ls_R_factor_gt           0.0506
_refine_ls_wR_factor_gt          0.1251
_refine_ls_wR_factor_ref         0.1416
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_refine_ls_number_reflns         5258
_refine_ls_number_parameters     239
_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)+(0.0566P)²+0.2704P] 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         0.285
_refine_diff_density_min         -0.369
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'APEX3 (Bruker AXS Inc., 2017)'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'XS, VERSION 2013/1'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  'APEX3 (Bruker AXS Inc., 2017)'

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
C C1 0.4058(2) 0.39308(16) 0.39376(16) 0.0564(4) Uani d . . . 1 . .
C C2 0.2937(3) 0.44541(19) 0.47715(16) 0.0632(5) Uani d . . . 1 . .
H H2 0.281457 0.396065 0.536201 0.076 Uiso calc U . R 1 . .
C C3 0.1990(3) 0.57256(19) 0.47246(16) 0.0644(5) Uani d . . . 1 . .
H H3 0.120695 0.610027 0.527699 0.077 Uiso calc U . R 1 . .
C C4 0.2230(3) 0.64117(17) 0.38545(16) 0.0634(5) Uani d . . . 1 . .
C C5 0.3336(3) 0.5904(2) 0.30157(17) 0.0718(5) Uani d . . . 1 . .
H H5 0.345555 0.640273 0.242807 0.086 Uiso calc U . R 1 . .
C C6 0.4274(3) 0.4631(2) 0.30598(17) 0.0676(5) Uani d . . . 1 . .
H H6 0.503965 0.425646 0.250123 0.081 Uiso calc U . R 1 . .
O O1 0.52021(18) 0.26943(12) 0.40129(13) 0.0728(4) Uani d . . . 1 . .
C C8 0.4560(2) 0.16742(17) 0.37731(13) 0.0541(4) Uani d . . . 1 . .
C C9 0.5668(4) -0.0595(2) 0.35259(19) 0.0847(7) Uani d . . . 1 . .
H H9A 0.438701 -0.061388 0.370826 0.127 Uiso calc U . R 1 . .
H H9B 0.649778 -0.125157 0.390814 0.127 Uiso calc U . R 1 . .
H H9C 0.592009 -0.073663 0.279786 0.127 Uiso calc U . R 1 . .
C C10 0.7900(3) 0.0694(2) 0.3940(2) 0.0881(7) Uani d . . . 1 . .
H H10A 0.833199 0.119392 0.339447 0.132 Uiso calc U . R 1 . .
H H10B 0.869547 -0.015363 0.394117 0.132 Uiso calc U . R 1 . .
H H10C 0.794183 0.107956 0.459297 0.132 Uiso calc U . R 1 . .
C C11 0.1435(3) 0.62031(18) 0.93803(15) 0.0601(4) Uani d . . . 1 . .
C C12 0.2532(3) 0.5032(2) 0.96450(16) 0.0660(5) Uani d . . . 1 . .
H H12 0.315459 0.491143 1.025998 0.079 Uiso calc U . R 1 . .
C C13 0.2694(3) 0.40339(19) 0.89789(19) 0.0714(5) Uani d . . . 1 . .
H H13 0.343026 0.322752 0.913354 0.086 Uiso calc U . R 1 . .
C C14 0.1749(3) 0.4259(2) 0.80913(17) 0.0693(5) Uani d . . . 1 . .
C C15 0.0633(3) 0.5407(2) 0.78271(17) 0.0689(5) Uani d . . . 1 . .
H H15 -0.000444 0.551948 0.72172 0.083 Uiso calc U . R 1 . .
C C16 0.0476(3) 0.63993(19) 0.84918(16) 0.0671(5) Uani d . . . 1 . .
H H16 -0.027908 0.719964 0.833727 0.081 Uiso calc U . R 1 . .
O O2 0.1165(2) 0.71981(15) 1.00896(11) 0.0784(4) Uani d . . . 1 . .
C C18 0.2274(3) 0.80331(18) 0.99935(14) 0.0617(5) Uani d . . . 1 . .
C C19 0.2831(5) 0.9875(3) 1.0818(2) 0.1108(10) Uani d . . . 1 . .
H H19A 0.415706 0.949485 1.07627 0.166 Uiso calc U . R 1 . .
H H19B 0.251212 1.028131 1.147483 0.166 Uiso calc U . R 1 . .
H H19C 0.250478 1.049847 1.027146 0.166 Uiso calc U . R 1 . .
C C20 0.0245(5) 0.8930(3) 1.14884(19) 0.1063(10) Uani d . . . 1 . .
H H20A -0.072798 0.96852 1.137257 0.159 Uiso calc U . R 1 . .
H H20B 0.067889 0.893716 1.217357 0.159 Uiso calc U . R 1 . .
H H20C -0.024396 0.819009 1.141721 0.159 Uiso calc U . R 1 . .
F F1 0.1328(2) 0.76708(12) 0.38189(12) 0.0943(4) Uani d . . . 1 . .
F F2 0.1931(3) 0.32811(14) 0.74186(13) 0.1056(5) Uani d . . . 1 . .
N N1 0.5967(2) 0.06371(15) 0.37724(12) 0.0618(4) Uani d . . . 1 . .
N N2 0.1798(3) 0.88937(17) 1.07361(13) 0.0774(5) Uani d . . . 1 . .
S S1 0.23411(7) 0.17432(5) 0.35549(5) 0.07179(18) Uani d . . . 1 . .
S S2 0.39605(8) 0.79751(5) 0.90809(5) 0.07508(19) Uani d . . . 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
C1 C6 . 1.367(3) ?
C1 C2 . 1.370(3) ?
C1 O1 . 1.399(2) ?
C2 C3 . 1.383(3) ?
C3 C4 . 1.354(3) ?
C4 F1 . 1.362(2) ?
C4 C5 . 1.364(3) ?
C5 C6 . 1.383(3) ?
O1 C8 . 1.349(2) ?
C8 N1 . 1.328(2) ?
C8 S1 . 1.6510(19) ?
C9 N1 . 1.448(3) ?
C10 N1 . 1.462(3) ?
C11 C16 . 1.366(3) ?
C11 C12 . 1.370(3) ?
C11 O2 . 1.407(2) ?
C12 C13 . 1.381(3) ?
C13 C14 . 1.360(3) ?
C14 C15 . 1.356(3) ?
C14 F2 . 1.368(2) ?
C15 C16 . 1.375(3) ?
O2 C18 . 1.351(3) ?
C18 N2 . 1.332(2) ?
C18 S2 . 1.652(2) ?
C19 N2 . 1.453(3) ?
C20 N2 . 1.450(3) ?

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
C6 C1 C2 . . 121.88(17) ?
C6 C1 O1 . . 117.63(17) ?
C2 C1 O1 . . 120.04(18) ?
C1 C2 C3 . . 119.17(18) ?
C4 C3 C2 . . 118.37(18) ?
C3 C4 F1 . . 118.27(18) ?
C3 C4 C5 . . 123.18(18) ?
F1 C4 C5 . . 118.54(19) ?
C4 C5 C6 . . 118.5(2) ?
C1 C6 C5 . . 118.92(18) ?
C8 O1 C1 . . 120.84(13) ?
N1 C8 O1 . . 109.43(15) ?
N1 C8 S1 . . 126.71(15) ?
O1 C8 S1 . . 123.84(13) ?
C16 C11 C12 . . 121.88(18) ?
C16 C11 O2 . . 119.24(18) ?
C12 C11 O2 . . 118.65(18) ?
C11 C12 C13 . . 118.58(19) ?
C14 C13 C12 . . 118.39(19) ?
C15 C14 C13 . . 123.72(19) ?
C15 C14 F2 . . 117.6(2) ?
C13 C14 F2 . . 118.7(2) ?
C14 C15 C16 . . 117.7(2) ?
C11 C16 C15 . . 119.67(19) ?
C18 O2 C11 . . 119.23(15) ?
N2 C18 O2 . . 109.92(18) ?
N2 C18 S2 . . 125.89(17) ?
O2 C18 S2 . . 124.20(14) ?
C8 N1 C9 . . 120.89(18) ?
C8 N1 C10 . . 122.06(17) ?
C9 N1 C10 . . 116.89(18) ?
C18 N2 C20 . . 123.3(2) ?
C18 N2 C19 . . 120.4(2) ?
C20 N2 C19 . . 116.3(2) ?

####################################################################### 
# 
# 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_fg916m
_database_code_depnum_ccdc_archive 'CCDC 1831303'
loop_
_audit_author_name
_audit_author_address
'Rakesh Ganguly'
;Nanyang Technological University
Singapore
;
_audit_update_record             
;
2018-03-21 deposited with the CCDC.	2020-10-30 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H17 N O S'
_chemical_formula_iupac          ?
_chemical_formula_weight         307.39

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_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                   17.044(2)
_cell_length_b                   5.7630(7)
_cell_length_c                   18.072(2)
_cell_angle_alpha                90
_cell_angle_beta                 117.231(4)
_cell_angle_gamma                90
_cell_volume                     1578.4(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2157
_cell_measurement_theta_min      2.5350
_cell_measurement_theta_max      26.1226
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.020
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             648

_exptl_absorpt_coefficient_mu    0.206
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.54
_exptl_absorpt_correction_T_max  1.00

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'Incoatec microfocus source'
_diffrn_source_type              'Bruker D8 Quest'

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'Multilayer Mirror'

_diffrn_measurement_device_type  'Photon II CPADs detector'
_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 7.4074

_diffrn_reflns_number            11516
_diffrn_reflns_av_R_equivalents  0.1042
_diffrn_reflns_av_unetI/netI     0.1026
_diffrn_reflns_theta_min         2.69
_diffrn_reflns_theta_max         26.41
_diffrn_reflns_theta_full        26.41
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22

_refine_special_details          
;
;

_reflns_number_total             3228
_reflns_number_gt                2163
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1248
_refine_ls_R_factor_gt           0.0903
_refine_ls_wR_factor_gt          0.2083
_refine_ls_wR_factor_ref         0.2399
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.016
_refine_ls_number_reflns         3228
_refine_ls_number_parameters     201
_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)+(0.1470P)²] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         1.130
_refine_diff_density_min         -1.062
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'APEX3 (Bruker AXS Inc., 2017)'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'XS, VERSION 2013/1'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  'APEX3 (Bruker AXS Inc., 2017)'

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
C C1 0.2836(2) 0.5192(6) 0.5629(2) 0.0190(8) Uani d . . . 1 . .
C C2 0.4427(3) 0.5154(8) 0.6506(3) 0.0328(10) Uani d . . . 1 . .
H H2A 0.456055 0.462607 0.606017 0.049 Uiso calc U . R 1 . .
H H2B 0.485665 0.448967 0.703683 0.049 Uiso calc U . R 1 . .
H H2C 0.445951 0.685107 0.653958 0.049 Uiso calc U . R 1 . .
C C3 0.3434(2) 0.2898(6) 0.6917(2) 0.0212(8) Uani d . . . 1 . .
C C4 0.3761(2) 0.3610(6) 0.7735(2) 0.0210(8) Uani d . . . 1 . .
H H4 0.403802 0.508425 0.789391 0.025 Uiso calc U . R 1 . .
C C5 0.3693(3) 0.2205(6) 0.8332(2) 0.0222(8) Uani d . . . 1 . .
C C6 0.4059(3) 0.2997(7) 0.9224(2) 0.0307(10) Uani d . . . 1 . .
H H6A 0.469197 0.265417 0.951831 0.046 Uiso calc U . R 1 . .
H H6B 0.375571 0.21804 0.949489 0.046 Uiso calc U . R 1 . .
H H6C 0.396768 0.46723 0.923836 0.046 Uiso calc U . R 1 . .
C C7 0.3280(3) 0.0061(6) 0.8079(2) 0.0227(8) Uani d . . . 1 . .
H H7 0.321977 -0.092218 0.847148 0.027 Uiso calc U . R 1 . .
C C8 0.2956(3) -0.0656(6) 0.7258(2) 0.0236(8) Uani d . . . 1 . .
H H8 0.267624 -0.212516 0.709689 0.028 Uiso calc U . R 1 . .
C C9 0.3034(3) 0.0729(6) 0.6674(2) 0.0225(8) Uani d . . . 1 . .
H H9 0.281857 0.021625 0.61149 0.027 Uiso calc U . R 1 . .
C C10 0.1269(2) 0.4919(6) 0.4893(2) 0.0204(8) Uani d . . . 1 . .
C C11 0.0920(2) 0.3315(6) 0.4274(2) 0.0182(8) Uani d . . . 1 . .
H H11 0.123678 0.194085 0.429407 0.022 Uiso calc U . R 1 . .
C C12 0.0071(2) 0.3732(6) 0.3596(2) 0.0188(8) Uani d . . . 1 . .
C C13 -0.0330(3) 0.2137(6) 0.2929(2) 0.0204(8) Uani d . . . 1 . .
H H13 -0.003571 0.073016 0.293685 0.024 Uiso calc U . R 1 . .
C C14 -0.1136(3) 0.2604(6) 0.2275(2) 0.0230(8) Uani d . . . 1 . .
H H14 -0.139095 0.153641 0.182631 0.028 Uiso calc U . R 1 . .
C C15 -0.1591(3) 0.4648(6) 0.2262(2) 0.0221(8) Uani d . . . 1 . .
H H15 -0.215095 0.495195 0.18058 0.027 Uiso calc U . R 1 . .
C C16 -0.1229(2) 0.6210(6) 0.2905(2) 0.0215(8) Uani d . . . 1 . .
H H16 -0.154416 0.758206 0.289276 0.026 Uiso calc U . R 1 . .
C C17 -0.0388(2) 0.5789(6) 0.3590(2) 0.0188(8) Uani d . . . 1 . .
C C18 0.0011(3) 0.7387(6) 0.4256(2) 0.0216(8) Uani d . . . 1 . .
H H18 -0.029088 0.87737 0.425352 0.026 Uiso calc U . R 1 . .
C C19 0.0827(3) 0.6957(6) 0.4902(2) 0.0227(8) Uani d . . . 1 . .
H H19 0.108822 0.802426 0.53504 0.027 Uiso calc U . R 1 . .
N N1 0.3531(2) 0.4393(5) 0.63265(18) 0.0204(7) Uani d . . . 1 . .
O O1 0.20747(17) 0.4409(4) 0.55989(15) 0.0231(6) Uani d . . . 1 . .
S S1 0.29030(7) 0.69061(16) 0.49283(6) 0.0243(3) Uani d . . . 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
C1 O1 . 1.352(4) ?
C1 N1 . 1.355(5) ?
C1 S1 . 1.650(4) ?
C2 N1 . 1.476(5) ?
C3 C4 . 1.381(5) ?
C3 C9 . 1.395(5) ?
C3 N1 . 1.440(5) ?
C4 C5 . 1.396(5) ?
C5 C7 . 1.391(5) ?
C5 C6 . 1.509(5) ?
C7 C8 . 1.387(5) ?
C8 C9 . 1.378(5) ?
C10 C11 . 1.359(5) ?
C10 C19 . 1.400(5) ?
C10 O1 . 1.413(4) ?
C11 C12 . 1.426(5) ?
C12 C17 . 1.418(5) ?
C12 C13 . 1.418(5) ?
C13 C14 . 1.368(5) ?
C14 C15 . 1.404(5) ?
C15 C16 . 1.373(5) ?
C16 C17 . 1.422(5) ?
C17 C18 . 1.418(5) ?
C18 C19 . 1.368(5) ?

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
O1 C1 N1 . . 109.8(3) ?
O1 C1 S1 . . 124.8(3) ?
N1 C1 S1 . . 125.4(3) ?
C4 C3 C9 . . 120.3(3) ?
C4 C3 N1 . . 119.2(3) ?
C9 C3 N1 . . 120.5(3) ?
C3 C4 C5 . . 121.2(3) ?
C7 C5 C4 . . 118.0(3) ?
C7 C5 C6 . . 121.3(3) ?
C4 C5 C6 . . 120.7(3) ?
C8 C7 C5 . . 120.7(3) ?
C9 C8 C7 . . 121.1(3) ?
C8 C9 C3 . . 118.8(3) ?
C11 C10 C19 . . 123.0(4) ?
C11 C10 O1 . . 118.7(3) ?
C19 C10 O1 . . 118.0(3) ?
C10 C11 C12 . . 118.9(3) ?
C17 C12 C13 . . 119.1(3) ?
C17 C12 C11 . . 119.2(3) ?
C13 C12 C11 . . 121.8(3) ?
C14 C13 C12 . . 120.6(3) ?
C13 C14 C15 . . 120.5(4) ?
C16 C15 C14 . . 120.4(4) ?
C15 C16 C17 . . 120.5(3) ?
C12 C17 C18 . . 119.1(3) ?
C12 C17 C16 . . 118.9(3) ?
C18 C17 C16 . . 122.0(3) ?
C19 C18 C17 . . 120.9(3) ?
C18 C19 C10 . . 118.9(3) ?
C1 N1 C3 . . 123.1(3) ?
C1 N1 C2 . . 118.6(3) ?
C3 N1 C2 . . 118.3(3) ?
C1 O1 C10 . . 119.0(3) ?

####################################################################### 
# 
# 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_fg794m
_database_code_depnum_ccdc_archive 'CCDC 1831304'
loop_
_audit_author_name
_audit_author_address
'Rakesh Ganguly'
;Nanyang Technological University
Singapore
;
_audit_update_record             
;
2018-03-21 deposited with the CCDC.	2020-10-30 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H9 Cl2 N O S'
_chemical_formula_iupac          ?
_chemical_formula_weight         250.13

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_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                   7.2726(2)
_cell_length_b                   7.4019(2)
_cell_length_c                   19.9994(4)
_cell_angle_alpha                90
_cell_angle_beta                 97.9720(10)
_cell_angle_gamma                90
_cell_volume                     1066.18(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9316
_cell_measurement_theta_min      3.1408
_cell_measurement_theta_max      33.1700
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.440
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.240
_exptl_crystal_density_diffrn    1.558
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             512

_exptl_absorpt_coefficient_mu    0.769
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.67
_exptl_absorpt_correction_T_max  0.84

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'Incoatec microfocus source'
_diffrn_source_type              'Bruker D8 Quest'

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'Multilayer Mirror'

_diffrn_measurement_device_type  'Photon II CPADs detector'
_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 7.4074

_diffrn_reflns_number            19201
_diffrn_reflns_av_R_equivalents  0.0378
_diffrn_reflns_av_unetI/netI     0.0310
_diffrn_reflns_theta_min         3.14
_diffrn_reflns_theta_max         33.18
_diffrn_reflns_theta_full        33.18
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       30

_refine_special_details          
;
;

_reflns_number_total             4034
_reflns_number_gt                3407
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0426
_refine_ls_R_factor_gt           0.0321
_refine_ls_wR_factor_gt          0.0740
_refine_ls_wR_factor_ref         0.0802
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_refine_ls_number_reflns         4034
_refine_ls_number_parameters     129
_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)+(0.0288P)²+0.5814P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.497
_refine_diff_density_min         -0.451
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'
Cl Cl 0.1484 0.1585 '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'

_computing_data_collection       'APEX3 (Bruker AXS Inc., 2017)'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'XT, VERSION 2014/5'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  'APEX3 (Bruker AXS Inc., 2017)'

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
C C1 0.62629(16) 0.66304(16) 0.56124(6) 0.0152(2) Uani d . . . 1 . .
C C2 0.45804(18) 0.66681(17) 0.58660(6) 0.0172(2) Uani d . . . 1 . .
C C3 0.30168(18) 0.74428(17) 0.55053(6) 0.0194(2) Uani d . . . 1 . .
H H3 0.188188 0.748948 0.56895 0.023 Uiso calc U . R 1 . .
C C4 0.31341(17) 0.81516(17) 0.48688(6) 0.0189(2) Uani d . . . 1 . .
H H4 0.207269 0.86959 0.461794 0.023 Uiso calc U . R 1 . .
C C5 0.47814(17) 0.80721(17) 0.45971(6) 0.0184(2) Uani d . . . 1 . .
H H5 0.484181 0.853061 0.415706 0.022 Uiso calc U . R 1 . .
C C6 0.63472(17) 0.73183(17) 0.49712(6) 0.0163(2) Uani d . . . 1 . .
C C7 0.86789(16) 0.65753(17) 0.65356(6) 0.0156(2) Uani d . . . 1 . .
C C8 1.06045(19) 0.5890(2) 0.75940(6) 0.0237(3) Uani d . . . 1 . .
H H8A 1.106153 0.712628 0.755576 0.036 Uiso calc U . R 1 . .
H H8B 1.166017 0.506676 0.769916 0.036 Uiso calc U . R 1 . .
H H8C 0.982338 0.583609 0.795535 0.036 Uiso calc U . R 1 . .
C C9 0.9288(2) 0.34056(17) 0.68528(7) 0.0217(2) Uani d . . . 1 . .
H H9A 0.841739 0.318049 0.644157 0.033 Uiso calc U . R 1 . .
H H9B 0.880129 0.286953 0.724064 0.033 Uiso calc U . R 1 . .
H H9C 1.049244 0.286176 0.680691 0.033 Uiso calc U . R 1 . .
Cl Cl1 0.44602(5) 0.56766(5) 0.66426(2) 0.02388(8) Uani d . . . 1 . .
Cl Cl2 0.84210(4) 0.72563(5) 0.46460(2) 0.02472(8) Uani d . . . 1 . .
N N1 0.95151(15) 0.53566(15) 0.69563(5) 0.01743(19) Uani d . . . 1 . .
O O1 0.77818(12) 0.57615(12) 0.59636(4) 0.01787(17) Uani d . . . 1 . .
S S1 0.87199(5) 0.88066(4) 0.66384(2) 0.02075(8) Uani d . . . 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
C1 O1 . 1.3828(14) ?
C1 C2 . 1.3883(17) ?
C1 C6 . 1.3890(16) ?
C2 C3 . 1.3838(18) ?
C2 Cl1 . 1.7310(12) ?
C3 C4 . 1.3903(18) ?
C4 C5 . 1.3836(18) ?
C5 C6 . 1.3897(17) ?
C6 Cl2 . 1.7239(12) ?
C7 N1 . 1.3228(15) ?
C7 O1 . 1.3747(14) ?
C7 S1 . 1.6641(13) ?
C8 N1 . 1.4595(16) ?
C9 N1 . 1.4649(17) ?

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
O1 C1 C2 . . 120.41(10) ?
O1 C1 C6 . . 120.34(11) ?
C2 C1 C6 . . 118.94(11) ?
C3 C2 C1 . . 121.34(11) ?
C3 C2 Cl1 . . 120.22(10) ?
C1 C2 Cl1 . . 118.43(9) ?
C2 C3 C4 . . 118.90(12) ?
C5 C4 C3 . . 120.66(11) ?
C4 C5 C6 . . 119.68(11) ?
C1 C6 C5 . . 120.42(11) ?
C1 C6 Cl2 . . 119.43(9) ?
C5 C6 Cl2 . . 120.14(9) ?
N1 C7 O1 . . 110.72(10) ?
N1 C7 S1 . . 126.83(9) ?
O1 C7 S1 . . 122.41(9) ?
C7 N1 C8 . . 121.15(11) ?
C7 N1 C9 . . 123.33(10) ?
C8 N1 C9 . . 115.29(10) ?
C7 O1 C1 . . 118.19(9) ?

