# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2017

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

data_compound3
_database_code_depnum_ccdc_archive 'CCDC 1575670'
_audit_update_record             
;
2017-09-20 deposited with the CCDC.
2017-12-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H13 N O3 S3'
_chemical_formula_weight         303.40

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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.0374(7)
_cell_length_b                   9.0824(10)
_cell_length_c                   13.2438(15)
_cell_angle_alpha                71.460(2)
_cell_angle_beta                 88.791(2)
_cell_angle_gamma                78.837(2)
_cell_volume                     674.86(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    3563
_cell_measurement_theta_min      2.41
_cell_measurement_theta_max      28.07

_exptl_crystal_description       blocks
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.493
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             316
_exptl_absorpt_coefficient_mu    0.548
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.9679
_exptl_absorpt_correction_T_max  0.9731
_exptl_absorpt_process_details   'Sheldrick, 1996'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6495
_diffrn_reflns_av_R_equivalents  0.0886
_diffrn_reflns_av_sigmaI/netI    0.0584
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.62
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2370
_reflns_number_gt                2139
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1130P)²+0.5225P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2370
_refine_ls_number_parameters     174
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0748
_refine_ls_R_factor_gt           0.0703
_refine_ls_wR_factor_ref         0.2115
_refine_ls_wR_factor_gt          0.2061
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.11578(16) 0.32029(11) 0.64374(7) 0.0609(4) Uani 1 1 d . . .
S2 S -0.1376(2) 0.44620(16) 0.83740(11) 0.0882(5) Uani 1 1 d . . .
C1 C 0.2498(6) 0.1543(4) 0.7478(3) 0.0550(8) Uani 1 1 d . A .
O1 O -0.1190(5) 0.3218(4) 0.6404(2) 0.0779(9) Uani 1 1 d . A .
C2 C 0.1255(6) 0.0780(4) 0.8299(3) 0.0586(9) Uani 1 1 d . . .
H2 H -0.0284 0.1165 0.8319 0.070 Uiso 1 1 calc R A .
C4 C 0.4606(6) -0.1155(4) 0.9074(3) 0.0589(9) Uani 1 1 d . . .
O2 O 0.2415(6) 0.3308(4) 0.5503(2) 0.0823(9) Uani 1 1 d . A .
C5 C 0.5803(7) -0.0376(5) 0.8243(4) 0.0712(11) Uani 1 1 d . A .
H5 H 0.7339 -0.0767 0.8223 0.085 Uiso 1 1 calc R . .
C7 C 0.5746(8) -0.2617(5) 0.9938(4) 0.0816(13) Uani 1 1 d . A .
H7A H 0.5184 -0.3516 0.9895 0.122 Uiso 1 1 calc R . .
H7B H 0.5434 -0.2485 1.0621 0.122 Uiso 1 1 calc R . .
H7C H 0.7348 -0.2785 0.9850 0.122 Uiso 1 1 calc R . .
C3 C 0.2312(7) -0.0548(5) 0.9082(3) 0.0645(10) Uani 1 1 d . A .
H3A H 0.1474 -0.1057 0.9634 0.077 Uiso 1 1 calc R . .
C6 C 0.4793(7) 0.0961(5) 0.7446(4) 0.0694(10) Uani 1 1 d . . .
H6 H 0.5633 0.1469 0.6894 0.083 Uiso 1 1 calc R A .
N1 N 0.1550(5) 0.4781(3) 0.6761(3) 0.0598(8) Uani 1 1 d . A 1
C8 C 0.3494(8) 0.5537(5) 0.6315(4) 0.0802(12) Uani 1 1 d . A 1
H8A H 0.3452 0.5812 0.5544 0.096 Uiso 1 1 calc R A 1
H8B H 0.4912 0.4819 0.6598 0.096 Uiso 1 1 calc R A 1
C9 C 0.3271(11) 0.7019(6) 0.6640(5) 0.1026(17) Uani 1 1 d . A 1
H9 H 0.4787 0.7174 0.6772 0.123 Uiso 1 1 calc R A 1
C10 C 0.200(2) 0.8499(14) 0.5872(7) 0.199(5) Uani 1 1 d . A 1
H10A H 0.0564 0.8321 0.5669 0.239 Uiso 1 1 calc R A 1
H10B H 0.1692 0.9321 0.6206 0.239 Uiso 1 1 calc R A 1
O3 O 0.316(3) 0.8964(9) 0.5019(8) 0.268(5) Uani 1 1 d . A 1
H3 H 0.3334 0.9868 0.4931 0.402 Uiso 1 1 calc R A 1
S3A S 0.1820(4) 0.6612(3) 0.78852(18) 0.0881(6) Uani 0.80 1 d P A 1
C11 C 0.0557(7) 0.5199(5) 0.7602(3) 0.0676(10) Uani 1 1 d . A 1
S3B S 0.1007(19) 0.7068(12) 0.7379(10) 0.106(3) Uani 0.20 1 d P B 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O1 1.416(3) . ?
S1 O2 1.425(3) . ?
S1 N1 1.679(3) . ?
S1 C1 1.755(4) . ?
S2 C11 1.634(5) . ?
C1 C2 1.384(5) . ?
C1 C6 1.389(5) . ?
C2 C3 1.368(5) . ?
C2 H2 0.9300 . ?
C4 C5 1.379(6) . ?
C4 C3 1.389(6) . ?
C4 C7 1.503(6) . ?
C5 C6 1.373(6) . ?
C5 H5 0.9300 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C3 H3A 0.9300 . ?
C6 H6 0.9300 . ?
N1 C11 1.378(5) . ?
N1 C8 1.491(5) . ?
C8 C9 1.520(7) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.482(11) . ?
C9 S3A 1.817(7) . ?
C9 H9 0.9800 . ?
C10 O3 1.311(11) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
O3 H3 0.8200 . ?
S3A C11 1.751(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S1 O2 120.2(2) . . ?
O1 S1 N1 108.61(17) . . ?
O2 S1 N1 103.26(17) . . ?
O1 S1 C1 109.47(18) . . ?
O2 S1 C1 108.79(18) . . ?
N1 S1 C1 105.49(16) . . ?
C2 C1 C6 120.3(3) . . ?
C2 C1 S1 120.1(3) . . ?
C6 C1 S1 119.5(3) . . ?
C3 C2 C1 119.3(3) . . ?
C3 C2 H2 120.4 . . ?
C1 C2 H2 120.4 . . ?
C5 C4 C3 117.8(4) . . ?
C5 C4 C7 121.0(4) . . ?
C3 C4 C7 121.2(4) . . ?
C6 C5 C4 121.9(4) . . ?
C6 C5 H5 119.0 . . ?
C4 C5 H5 119.0 . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C2 C3 C4 121.7(4) . . ?
C2 C3 H3A 119.1 . . ?
C4 C3 H3A 119.1 . . ?
C5 C6 C1 118.9(4) . . ?
C5 C6 H6 120.5 . . ?
C1 C6 H6 120.5 . . ?
C11 N1 C8 115.6(4) . . ?
C11 N1 S1 123.9(3) . . ?
C8 N1 S1 118.6(3) . . ?
N1 C8 C9 106.8(4) . . ?
N1 C8 H8A 110.4 . . ?
C9 C8 H8A 110.4 . . ?
N1 C8 H8B 110.4 . . ?
C9 C8 H8B 110.4 . . ?
H8A C8 H8B 108.6 . . ?
C10 C9 C8 115.9(7) . . ?
C10 C9 S3A 108.6(5) . . ?
C8 C9 S3A 105.9(4) . . ?
C10 C9 H9 108.8 . . ?
C8 C9 H9 108.8 . . ?
S3A C9 H9 108.8 . . ?
O3 C10 C9 110.6(10) . . ?
O3 C10 H10A 109.5 . . ?
C9 C10 H10A 109.5 . . ?
O3 C10 H10B 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 108.1 . . ?
C11 S3A C9 92.7(2) . . ?
N1 C11 S2 129.2(3) . . ?
N1 C11 S3A 111.1(3) . . ?
S2 C11 S3A 119.5(3) . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.784
_refine_diff_density_min         -0.505
_refine_diff_density_rms         0.071
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_Compound49
_database_code_depnum_ccdc_archive 'CCDC 1587468'
_audit_update_record             
;
2017-11-24 deposited with the CCDC.
2017-12-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H28 N O5 P S'
_chemical_formula_weight         449.48

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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   15.4813(7)
_cell_length_b                   13.2156(6)
_cell_length_c                   11.7370(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.0030(10)
_cell_angle_gamma                90.00
_cell_volume                     2377.94(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9927
_cell_measurement_theta_min      2.33
_cell_measurement_theta_max      25.92

_exptl_crystal_description       blocks
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.256
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             952
_exptl_absorpt_coefficient_mu    0.235
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            48349
_diffrn_reflns_av_R_equivalents  0.0406
_diffrn_reflns_av_sigmaI/netI    0.0165
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.33
_diffrn_reflns_theta_max         25.00
_reflns_number_total             4165
_reflns_number_gt                3357
_reflns_threshold_expression     >2sigma(I)

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

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0906P)²+1.8488P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4165
_refine_ls_number_parameters     280
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0757
_refine_ls_R_factor_gt           0.0625
_refine_ls_wR_factor_ref         0.1792
_refine_ls_wR_factor_gt          0.1686
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.15857(6) 0.40238(6) 0.14124(8) 0.0626(3) Uani 1 1 d . . .
P1 P 0.38035(5) 0.60773(7) 0.30559(7) 0.0591(3) Uani 1 1 d . . .
O2 O 0.44956(14) 0.6745(2) 0.25349(17) 0.0714(7) Uani 1 1 d . . .
O3 O 0.39054(14) 0.6403(2) 0.43565(17) 0.0686(6) Uani 1 1 d . . .
O5 O 0.09749(18) 0.4282(2) 0.0430(2) 0.0793(7) Uani 1 1 d . . .
O4 O 0.21323(18) 0.31537(17) 0.1379(3) 0.0881(8) Uani 1 1 d . . .
N1 N 0.22837(19) 0.49420(19) 0.1707(3) 0.0604(7) Uani 1 1 d . . .
O1 O 0.39091(17) 0.4988(2) 0.2886(3) 0.0932(9) Uani 1 1 d . . .
C9 C 0.26533(16) 0.7675(2) 0.2578(2) 0.0436(6) Uani 1 1 d . . .
C7 C 0.21294(18) 0.59631(19) 0.1916(2) 0.0461(6) Uani 1 1 d . . .
C6 C 0.27699(18) 0.6557(2) 0.2450(2) 0.0469(6) Uani 1 1 d . . .
C14 C 0.28327(19) 0.8336(2) 0.1725(2) 0.0537(7) Uani 1 1 d . . .
H14 H 0.3012 0.8080 0.1059 0.064 Uiso 1 1 calc R . .
C17 C 0.0135(2) 0.4070(2) 0.2492(3) 0.0642(8) Uani 1 1 d . . .
H17 H -0.0173 0.4260 0.1787 0.077 Uiso 1 1 calc R . .
C10 C 0.2383(2) 0.8091(2) 0.3552(2) 0.0566(7) Uani 1 1 d . . .
H10 H 0.2254 0.7666 0.4137 0.068 Uiso 1 1 calc R . .
C8 C 0.12423(19) 0.6355(2) 0.1477(3) 0.0582(8) Uani 1 1 d . . .
H8A H 0.0816 0.6002 0.1847 0.087 Uiso 1 1 calc R . .
H8B H 0.1124 0.6250 0.0661 0.087 Uiso 1 1 calc R . .
H8C H 0.1216 0.7065 0.1640 0.087 Uiso 1 1 calc R . .
C16 C 0.1016(2) 0.3910(2) 0.2600(3) 0.0560(7) Uani 1 1 d . . .
C13 C 0.2750(2) 0.9367(2) 0.1848(3) 0.0648(8) Uani 1 1 d . . .
H13 H 0.2879 0.9791 0.1262 0.078 Uiso 1 1 calc R . .
C12 C 0.2480(2) 0.9788(2) 0.2815(3) 0.0668(9) Uani 1 1 d . . .
C11 C 0.2303(2) 0.9126(2) 0.3670(3) 0.0659(9) Uani 1 1 d . . .
H11 H 0.2126 0.9385 0.4337 0.079 Uiso 1 1 calc R . .
C18 C -0.0292(2) 0.3947(3) 0.3433(4) 0.0736(10) Uani 1 1 d . . .
H18 H -0.0890 0.4061 0.3357 0.088 Uiso 1 1 calc R . .
C21 C 0.1472(3) 0.3627(3) 0.3653(4) 0.0792(10) Uani 1 1 d . . .
H21 H 0.2071 0.3521 0.3727 0.095 Uiso 1 1 calc R . .
C19 C 0.0146(3) 0.3658(2) 0.4490(3) 0.0746(10) Uani 1 1 d . . .
C20 C 0.1039(3) 0.3506(3) 0.4578(4) 0.0877(12) Uani 1 1 d . . .
H20 H 0.1349 0.3318 0.5283 0.105 Uiso 1 1 calc R . .
C2 C 0.5313(2) 0.7242(5) 0.4380(3) 0.0899(13) Uani 1 1 d . . .
C22 C -0.0326(4) 0.3508(3) 0.5511(4) 0.1101(17) Uani 1 1 d . . .
H22A H -0.0846 0.3913 0.5423 0.165 Uiso 1 1 calc R . .
H22B H 0.0045 0.3706 0.6199 0.165 Uiso 1 1 calc R . .
H22C H -0.0480 0.2807 0.5565 0.165 Uiso 1 1 calc R . .
C3 C 0.4716(3) 0.6592(5) 0.4997(3) 0.121(2) Uani 1 1 d . . .
H3A H 0.5003 0.5951 0.5197 0.146 Uiso 1 1 calc R . .
H3B H 0.4627 0.6926 0.5707 0.146 Uiso 1 1 calc R . .
C15 C 0.2337(4) 1.0916(3) 0.2939(5) 0.1118(17) Uani 1 1 d . . .
H15A H 0.2550 1.1268 0.2319 0.168 Uiso 1 1 calc R . .
H15B H 0.2646 1.1145 0.3659 0.168 Uiso 1 1 calc R . .
H15C H 0.1726 1.1049 0.2918 0.168 Uiso 1 1 calc R . .
C1 C 0.5320(3) 0.6869(7) 0.3184(4) 0.164(3) Uani 1 1 d . . .
H1A H 0.5653 0.7340 0.2784 0.197 Uiso 1 1 calc R . .
H1B H 0.5621 0.6224 0.3220 0.197 Uiso 1 1 calc R . .
C5 C 0.6223(3) 0.7070(6) 0.5008(5) 0.154(3) Uani 1 1 d . . .
H5A H 0.6633 0.7457 0.4645 0.231 Uiso 1 1 calc R . .
H5B H 0.6366 0.6365 0.4982 0.231 Uiso 1 1 calc R . .
H5C H 0.6247 0.7281 0.5794 0.231 Uiso 1 1 calc R . .
C4 C 0.5007(5) 0.8261(6) 0.4361(7) 0.166(3) Uani 1 1 d . . .
H4A H 0.5473 0.8698 0.4683 0.249 Uiso 1 1 calc R . .
H4B H 0.4533 0.8311 0.4806 0.249 Uiso 1 1 calc R . .
H4C H 0.4809 0.8459 0.3581 0.249 Uiso 1 1 calc R . .
H23 H 0.277(2) 0.483(3) 0.200(3) 0.064(11) Uiso 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O5 1.427(3) . ?
S1 O4 1.431(2) . ?
S1 N1 1.630(3) . ?
S1 C16 1.757(4) . ?
P1 O1 1.466(3) . ?
P1 O3 1.573(2) . ?
P1 O2 1.576(2) . ?
P1 C6 1.775(3) . ?
O2 C1 1.402(5) . ?
O3 C3 1.392(4) . ?
N1 C7 1.398(4) . ?
N1 H23 0.80(4) . ?
C9 C10 1.384(4) . ?
C9 C14 1.385(4) . ?
C9 C6 1.498(4) . ?
C7 C6 1.349(4) . ?
C7 C8 1.491(4) . ?
C14 C13 1.378(4) . ?
C14 H14 0.9300 . ?
C17 C16 1.369(5) . ?
C17 C18 1.373(5) . ?
C17 H17 0.9300 . ?
C10 C11 1.383(4) . ?
C10 H10 0.9300 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C16 C21 1.386(5) . ?
C13 C12 1.380(5) . ?
C13 H13 0.9300 . ?
C12 C11 1.386(5) . ?
C12 C15 1.517(5) . ?
C11 H11 0.9300 . ?
C18 C19 1.382(6) . ?
C18 H18 0.9300 . ?
C21 C20 1.363(6) . ?
C21 H21 0.9300 . ?
C19 C20 1.386(6) . ?
C19 C22 1.502(6) . ?
C20 H20 0.9300 . ?
C2 C4 1.426(9) . ?
C2 C1 1.490(6) . ?
C2 C5 1.513(7) . ?
C2 C3 1.517(6) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O5 S1 O4 119.87(17) . . ?
O5 S1 N1 109.78(16) . . ?
O4 S1 N1 103.12(16) . . ?
O5 S1 C16 108.20(16) . . ?
O4 S1 C16 108.48(15) . . ?
N1 S1 C16 106.63(14) . . ?
O1 P1 O3 113.72(16) . . ?
O1 P1 O2 113.73(16) . . ?
O3 P1 O2 104.00(12) . . ?
O1 P1 C6 114.09(15) . . ?
O3 P1 C6 104.70(13) . . ?
O2 P1 C6 105.57(13) . . ?
C1 O2 P1 118.1(3) . . ?
C3 O3 P1 122.3(2) . . ?
C7 N1 S1 129.2(2) . . ?
C7 N1 H23 106(3) . . ?
S1 N1 H23 121(3) . . ?
C10 C9 C14 117.4(3) . . ?
C10 C9 C6 121.9(2) . . ?
C14 C9 C6 120.7(2) . . ?
C6 C7 N1 120.7(3) . . ?
C6 C7 C8 122.7(2) . . ?
N1 C7 C8 116.5(3) . . ?
C7 C6 C9 122.0(2) . . ?
C7 C6 P1 122.8(2) . . ?
C9 C6 P1 115.3(2) . . ?
C13 C14 C9 121.2(3) . . ?
C13 C14 H14 119.4 . . ?
C9 C14 H14 119.4 . . ?
C16 C17 C18 119.5(3) . . ?
C16 C17 H17 120.3 . . ?
C18 C17 H17 120.3 . . ?
C11 C10 C9 121.2(3) . . ?
C11 C10 H10 119.4 . . ?
C9 C10 H10 119.4 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C17 C16 C21 120.1(3) . . ?
C17 C16 S1 121.1(3) . . ?
C21 C16 S1 118.8(3) . . ?
C14 C13 C12 121.8(3) . . ?
C14 C13 H13 119.1 . . ?
C12 C13 H13 119.1 . . ?
C13 C12 C11 117.1(3) . . ?
C13 C12 C15 122.6(3) . . ?
C11 C12 C15 120.2(3) . . ?
C10 C11 C12 121.4(3) . . ?
C10 C11 H11 119.3 . . ?
C12 C11 H11 119.3 . . ?
C17 C18 C19 121.6(4) . . ?
C17 C18 H18 119.2 . . ?
C19 C18 H18 119.2 . . ?
C20 C21 C16 119.8(4) . . ?
C20 C21 H21 120.1 . . ?
C16 C21 H21 120.1 . . ?
C18 C19 C20 117.8(4) . . ?
C18 C19 C22 121.4(4) . . ?
C20 C19 C22 120.9(4) . . ?
C21 C20 C19 121.3(4) . . ?
C21 C20 H20 119.4 . . ?
C19 C20 H20 119.4 . . ?
C4 C2 C1 110.1(6) . . ?
C4 C2 C5 115.7(6) . . ?
C1 C2 C5 106.3(4) . . ?
C4 C2 C3 108.6(5) . . ?
C1 C2 C3 110.3(4) . . ?
C5 C2 C3 105.7(4) . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O3 C3 C2 114.0(3) . . ?
O3 C3 H3A 108.7 . . ?
C2 C3 H3A 108.7 . . ?
O3 C3 H3B 108.7 . . ?
C2 C3 H3B 108.7 . . ?
H3A C3 H3B 107.6 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O2 C1 C2 115.2(4) . . ?
O2 C1 H1A 108.5 . . ?
C2 C1 H1A 108.5 . . ?
O2 C1 H1B 108.5 . . ?
C2 C1 H1B 108.5 . . ?
H1A C1 H1B 107.5 . . ?
C2 C5 H5A 109.5 . . ?
C2 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C2 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C2 C4 H4A 109.5 . . ?
C2 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C2 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.798
_refine_diff_density_min         -0.617
_refine_diff_density_rms         0.051
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_compound27
_database_code_depnum_ccdc_archive 'CCDC 1575672'
_audit_update_record             
;
2017-09-20 deposited with the CCDC.
2017-12-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H11 N O2 S3'
_chemical_formula_weight         273.38

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   6.1417(8)
_cell_length_b                   9.6650(13)
_cell_length_c                   20.803(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.498(2)
_cell_angle_gamma                90.00
_cell_volume                     1224.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    5497
_cell_measurement_theta_min      2.33
_cell_measurement_theta_max      28.23

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.483
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             568
_exptl_absorpt_coefficient_mu    0.589
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.8716
_exptl_absorpt_correction_T_max  0.9117
_exptl_absorpt_process_details   'SADABS, Sheldrick, 1996'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11356
_diffrn_reflns_av_R_equivalents  0.0604
_diffrn_reflns_av_sigmaI/netI    0.0297
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.97
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2161
_reflns_number_gt                2114
_reflns_threshold_expression     >2sigma(I)

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

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0493P)²+1.0276P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2161
_refine_ls_number_parameters     146
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0574
_refine_ls_R_factor_gt           0.0560
_refine_ls_wR_factor_ref         0.1351
_refine_ls_wR_factor_gt          0.1341
_refine_ls_goodness_of_fit_ref   1.182
_refine_ls_restrained_S_all      1.182
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.41412(13) 0.68574(8) 0.38044(4) 0.0527(3) Uani 1 1 d . . .
S3 S 0.11356(17) 0.67176(11) 0.18714(4) 0.0687(3) Uani 1 1 d . . .
S2 S 0.51478(19) 0.53122(13) 0.24300(6) 0.0834(4) Uani 1 1 d . . .
C10 C 0.3166(5) 0.6367(3) 0.25185(15) 0.0513(7) Uani 1 1 d . . .
N1 N 0.2721(4) 0.7067(3) 0.30571(12) 0.0477(6) Uani 1 1 d . . .
C1 C 0.3531(5) 0.5168(3) 0.40345(13) 0.0451(7) Uani 1 1 d . . .
O2 O 0.3111(5) 0.7807(2) 0.41933(12) 0.0711(7) Uani 1 1 d . . .
C2 C 0.1536(5) 0.4918(3) 0.42553(15) 0.0513(7) Uani 1 1 d . . .
H2 H 0.0507 0.5622 0.4260 0.062 Uiso 1 1 calc R . .
O1 O 0.6410(4) 0.6963(3) 0.37560(13) 0.0728(7) Uani 1 1 d . . .
C4 C 0.2610(5) 0.2550(3) 0.44666(14) 0.0534(8) Uani 1 1 d . . .
C3 C 0.1099(5) 0.3616(4) 0.44661(15) 0.0550(8) Uani 1 1 d . . .
H3 H -0.0242 0.3444 0.4612 0.066 Uiso 1 1 calc R . .
C6 C 0.5043(5) 0.4118(4) 0.40156(16) 0.0568(8) Uani 1 1 d . . .
H6 H 0.6372 0.4284 0.3860 0.068 Uiso 1 1 calc R . .
C5 C 0.4555(6) 0.2821(4) 0.42301(17) 0.0643(9) Uani 1 1 d . . .
H5 H 0.5567 0.2110 0.4215 0.077 Uiso 1 1 calc R . .
C9 C -0.0148(6) 0.8022(4) 0.22986(19) 0.0735(11) Uani 1 1 d . . .
H9A H 0.0301 0.8935 0.2174 0.088 Uiso 1 1 calc R . .
H9B H -0.1733 0.7955 0.2205 0.088 Uiso 1 1 calc R . .
C7 C 0.2097(8) 0.1143(4) 0.4722(2) 0.0813(12) Uani 1 1 d . . .
H7A H 0.0589 0.0918 0.4580 0.122 Uiso 1 1 calc R . .
H7B H 0.2347 0.1153 0.5187 0.122 Uiso 1 1 calc R . .
H7C H 0.3030 0.0463 0.4561 0.122 Uiso 1 1 calc R . .
C8 C 0.0578(6) 0.7772(4) 0.30016(18) 0.0708(10) Uani 1 1 d . . .
H8A H 0.0714 0.8644 0.3235 0.085 Uiso 1 1 calc R . .
H8B H -0.0485 0.7200 0.3184 0.085 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O1 1.414(3) . ?
S1 O2 1.425(3) . ?
S1 N1 1.693(3) . ?
S1 C1 1.755(3) . ?
S3 C10 1.745(3) . ?
S3 C9 1.784(4) . ?
S2 C10 1.617(3) . ?
C10 N1 1.366(4) . ?
N1 C8 1.473(4) . ?
C1 C6 1.379(4) . ?
C1 C2 1.385(4) . ?
C2 C3 1.370(5) . ?
C2 H2 0.9300 . ?
C4 C5 1.375(5) . ?
C4 C3 1.386(5) . ?
C4 C7 1.508(5) . ?
C3 H3 0.9300 . ?
C6 C5 1.377(5) . ?
C6 H6 0.9300 . ?
C5 H5 0.9300 . ?
C9 C8 1.492(5) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S1 O2 120.57(17) . . ?
O1 S1 N1 108.69(15) . . ?
O2 S1 N1 103.34(14) . . ?
O1 S1 C1 109.52(15) . . ?
O2 S1 C1 108.53(15) . . ?
N1 S1 C1 104.99(13) . . ?
C10 S3 C9 94.05(17) . . ?
N1 C10 S2 129.8(2) . . ?
N1 C10 S3 109.7(2) . . ?
S2 C10 S3 120.5(2) . . ?
C10 N1 C8 115.9(3) . . ?
C10 N1 S1 124.0(2) . . ?
C8 N1 S1 118.4(2) . . ?
C6 C1 C2 120.6(3) . . ?
C6 C1 S1 120.5(2) . . ?
C2 C1 S1 118.9(2) . . ?
C3 C2 C1 119.0(3) . . ?
C3 C2 H2 120.5 . . ?
C1 C2 H2 120.5 . . ?
C5 C4 C3 118.1(3) . . ?
C5 C4 C7 121.9(3) . . ?
C3 C4 C7 120.0(3) . . ?
C2 C3 C4 121.6(3) . . ?
C2 C3 H3 119.2 . . ?
C4 C3 H3 119.2 . . ?
C5 C6 C1 119.0(3) . . ?
C5 C6 H6 120.5 . . ?
C1 C6 H6 120.5 . . ?
C4 C5 C6 121.7(3) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C8 C9 S3 106.2(3) . . ?
C8 C9 H9A 110.5 . . ?
S3 C9 H9A 110.5 . . ?
C8 C9 H9B 110.5 . . ?
S3 C9 H9B 110.5 . . ?
H9A C9 H9B 108.7 . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N1 C8 C9 107.5(3) . . ?
N1 C8 H8A 110.2 . . ?
C9 C8 H8A 110.2 . . ?
N1 C8 H8B 110.2 . . ?
C9 C8 H8B 110.2 . . ?
H8A C8 H8B 108.5 . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.357
_refine_diff_density_min         -0.262
_refine_diff_density_rms         0.054
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_compound13
_database_code_depnum_ccdc_archive 'CCDC 1575671'
_audit_update_record             
;
2017-09-20 deposited with the CCDC.
2017-12-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H17 Cl N2 O3 S2'
_chemical_formula_weight         396.90

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'

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

_cell_length_a                   10.9934(13)
_cell_length_b                   15.541(2)
_cell_length_c                   10.7812(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.582(4)
_cell_angle_gamma                90.00
_cell_volume                     1816.2(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4218
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      22.35

_exptl_crystal_description       blocks
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.452
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             824
_exptl_absorpt_coefficient_mu    0.459
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.9730
_exptl_absorpt_correction_T_max  0.9774
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            25364
_diffrn_reflns_av_R_equivalents  0.1254
_diffrn_reflns_av_sigmaI/netI    0.0655
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.29
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3193
_reflns_number_gt                2147
_reflns_threshold_expression     >2σ(I)

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

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0608P)²+8.9064P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3193
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1339
_refine_ls_R_factor_gt           0.0885
_refine_ls_wR_factor_ref         0.2073
_refine_ls_wR_factor_gt          0.1875
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.78848(14) 0.32347(11) 0.48436(16) 0.0439(5) Uani 1 1 d . . .
Cl1 Cl 0.09040(15) 0.30758(14) 0.77859(17) 0.0615(6) Uani 1 1 d . . .
S2 S 0.44742(16) 0.43718(14) 0.33600(17) 0.0565(6) Uani 1 1 d . . .
O1 O 0.7625(4) 0.2404(3) 0.5287(5) 0.0563(13) Uani 1 1 d . . .
N2 N 0.5349(4) 0.3324(3) 0.5395(4) 0.0331(11) Uani 1 1 d . . .
O2 O 0.8837(4) 0.3333(4) 0.4106(5) 0.0645(15) Uani 1 1 d . . .
N1 N 0.6620(4) 0.3604(4) 0.3907(5) 0.0421(13) Uani 1 1 d . . .
C12 C 0.4238(5) 0.3343(3) 0.5873(5) 0.0279(12) Uani 1 1 d . . .
O3 O 0.5778(5) 0.3894(4) 0.0191(5) 0.0794(17) Uani 1 1 d . . .
H4 H 0.6507 0.3805 0.0473 0.119 Uiso 1 1 calc R . .
C16 C 0.3335(5) 0.3313(4) 0.7774(5) 0.0366(14) Uani 1 1 d . . .
H16 H 0.3424 0.3347 0.8646 0.044 Uiso 1 1 calc R . .
C13 C 0.3068(5) 0.3255(4) 0.5175(5) 0.0351(14) Uani 1 1 d . . .
H13 H 0.2971 0.3242 0.4302 0.042 Uiso 1 1 calc R . .
C17 C 0.4351(5) 0.3365(4) 0.7180(5) 0.0341(14) Uani 1 1 d . . .
H17 H 0.5131 0.3416 0.7663 0.041 Uiso 1 1 calc R . .
C11 C 0.5492(5) 0.3676(4) 0.4365(6) 0.0350(14) Uani 1 1 d . . .
C14 C 0.2039(5) 0.3184(4) 0.5755(6) 0.0372(14) Uani 1 1 d . . .
H14 H 0.1259 0.3119 0.5277 0.045 Uiso 1 1 calc R . .
C1 C 0.8160(5) 0.3942(4) 0.6120(6) 0.0358(14) Uani 1 1 d . . .
C2 C 0.7840(5) 0.3743(4) 0.7271(6) 0.0387(15) Uani 1 1 d . . .
H2 H 0.7468 0.3219 0.7389 0.046 Uiso 1 1 calc R . .
C15 C 0.2185(5) 0.3211(4) 0.7052(6) 0.0381(15) Uani 1 1 d . . .
C4 C 0.8626(6) 0.5123(4) 0.8079(6) 0.0463(17) Uani 1 1 d . . .
C3 C 0.8074(6) 0.4324(5) 0.8238(6) 0.0460(16) Uani 1 1 d . . .
H3 H 0.7864 0.4186 0.9014 0.055 Uiso 1 1 calc R . .
C5 C 0.8943(6) 0.5299(4) 0.6919(7) 0.0500(18) Uani 1 1 d . . .
H5 H 0.9323 0.5820 0.6798 0.060 Uiso 1 1 calc R . .
C6 C 0.8710(5) 0.4727(4) 0.5940(6) 0.0423(16) Uani 1 1 d . . .
H6 H 0.8919 0.4863 0.5163 0.051 Uiso 1 1 calc R . .
C9 C 0.5463(6) 0.4447(4) 0.2206(6) 0.0476(17) Uani 1 1 d . . .
H9 H 0.5434 0.5033 0.1865 0.057 Uiso 1 1 calc R . .
C8 C 0.6763(6) 0.4260(5) 0.2932(6) 0.057(2) Uani 1 1 d . . .
H8A H 0.7291 0.4041 0.2367 0.069 Uiso 1 1 calc R . .
H8B H 0.7130 0.4781 0.3325 0.069 Uiso 1 1 calc R . .
C10 C 0.5072(7) 0.3827(5) 0.1175(7) 0.066(2) Uani 1 1 d . . .
H10A H 0.5147 0.3248 0.1514 0.079 Uiso 1 1 calc R . .
H10B H 0.4210 0.3925 0.0834 0.079 Uiso 1 1 calc R . .
C7 C 0.8835(8) 0.5761(5) 0.9151(8) 0.077(3) Uani 1 1 d . . .
H7A H 0.8555 0.5518 0.9873 0.115 Uiso 1 1 calc R . .
H7B H 0.8384 0.6279 0.8904 0.115 Uiso 1 1 calc R . .
H7C H 0.9699 0.5891 0.9357 0.115 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O1 1.422(5) . ?
S1 O2 1.424(5) . ?
S1 N1 1.678(5) . ?
S1 C1 1.747(6) . ?
Cl1 C15 1.739(6) . ?
S2 C11 1.786(6) . ?
S2 C9 1.788(7) . ?
N2 C11 1.272(7) . ?
N2 C12 1.402(7) . ?
N1 C11 1.413(7) . ?
N1 C8 1.491(8) . ?
C12 C13 1.385(8) . ?
C12 C17 1.395(8) . ?
O3 C10 1.419(9) . ?
O3 H4 0.8200 . ?
C16 C17 1.379(8) . ?
C16 C15 1.380(8) . ?
C16 H16 0.9300 . ?
C13 C14 1.385(8) . ?
C13 H13 0.9300 . ?
C17 H17 0.9300 . ?
C14 C15 1.381(8) . ?
C14 H14 0.9300 . ?
C1 C2 1.380(8) . ?
C1 C6 1.389(8) . ?
C2 C3 1.370(9) . ?
C2 H2 0.9300 . ?
C4 C5 1.381(9) . ?
C4 C3 1.404(9) . ?
C4 C7 1.511(10) . ?
C3 H3 0.9300 . ?
C5 C6 1.372(9) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C9 C10 1.479(9) . ?
C9 C8 1.539(9) . ?
C9 H9 0.9800 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S1 O2 119.5(3) . . ?
O1 S1 N1 108.7(3) . . ?
O2 S1 N1 103.9(3) . . ?
O1 S1 C1 108.9(3) . . ?
O2 S1 C1 109.0(3) . . ?
N1 S1 C1 106.0(3) . . ?
C11 S2 C9 94.0(3) . . ?
C11 N2 C12 123.6(5) . . ?
C11 N1 C8 113.2(5) . . ?
C11 N1 S1 120.2(4) . . ?
C8 N1 S1 118.9(4) . . ?
C13 C12 C17 118.0(5) . . ?
C13 C12 N2 125.9(5) . . ?
C17 C12 N2 115.8(5) . . ?
C10 O3 H4 109.5 . . ?
C17 C16 C15 118.8(5) . . ?
C17 C16 H16 120.6 . . ?
C15 C16 H16 120.6 . . ?
C12 C13 C14 121.2(5) . . ?
C12 C13 H13 119.4 . . ?
C14 C13 H13 119.4 . . ?
C16 C17 C12 121.7(5) . . ?
C16 C17 H17 119.2 . . ?
C12 C17 H17 119.2 . . ?
N2 C11 N1 121.0(5) . . ?
N2 C11 S2 129.4(4) . . ?
N1 C11 S2 109.5(4) . . ?
C15 C14 C13 119.3(5) . . ?
C15 C14 H14 120.4 . . ?
C13 C14 H14 120.4 . . ?
C2 C1 C6 120.2(6) . . ?
C2 C1 S1 122.1(5) . . ?
C6 C1 S1 117.7(5) . . ?
C3 C2 C1 119.6(6) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C16 C15 C14 121.0(5) . . ?
C16 C15 Cl1 119.5(5) . . ?
C14 C15 Cl1 119.4(5) . . ?
C5 C4 C3 117.7(6) . . ?
C5 C4 C7 122.2(7) . . ?
C3 C4 C7 120.1(7) . . ?
C2 C3 C4 121.3(6) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
C6 C5 C4 121.7(6) . . ?
C6 C5 H5 119.2 . . ?
C4 C5 H5 119.2 . . ?
C5 C6 C1 119.5(6) . . ?
C5 C6 H6 120.3 . . ?
C1 C6 H6 120.3 . . ?
C10 C9 C8 112.9(6) . . ?
C10 C9 S2 110.2(5) . . ?
C8 C9 S2 104.7(4) . . ?
C10 C9 H9 109.6 . . ?
C8 C9 H9 109.6 . . ?
S2 C9 H9 109.6 . . ?
N1 C8 C9 106.8(5) . . ?
N1 C8 H8A 110.4 . . ?
C9 C8 H8A 110.4 . . ?
N1 C8 H8B 110.4 . . ?
C9 C8 H8B 110.4 . . ?
H8A C8 H8B 108.6 . . ?
O3 C10 C9 112.8(6) . . ?
O3 C10 H10A 109.0 . . ?
C9 C10 H10A 109.0 . . ?
O3 C10 H10B 109.0 . . ?
C9 C10 H10B 109.0 . . ?
H10A C10 H10B 107.8 . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         1.346
_refine_diff_density_min         -0.753
_refine_diff_density_rms         0.087

_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_Compound40
_database_code_depnum_ccdc_archive 'CCDC 1575673'
_audit_update_record             
;
2017-09-20 deposited with the CCDC.
2017-12-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H19 Cl N2 O2 S2'
_chemical_formula_weight         394.92

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   17.218(7)
_cell_length_b                   7.657(3)
_cell_length_c                   14.611(6)
_cell_angle_alpha                90
_cell_angle_beta                 103.225(12)
_cell_angle_gamma                90
_cell_volume                     1875.2(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    292(2)
_cell_measurement_reflns_used    3462
_cell_measurement_theta_min      2.43
_cell_measurement_theta_max      21.99

_exptl_crystal_description       blocks
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.399
_exptl_crystal_F_000             824
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.060
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.440
_shelx_estimated_absorpt_T_min   0.974
_shelx_estimated_absorpt_T_max   0.978
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      292(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25407
_diffrn_reflns_av_unetI/netI     0.0937
_diffrn_reflns_av_R_equivalents  0.1759
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.430
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             3274
_reflns_number_gt                1899
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0528P)²+0.1817P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3274
_refine_ls_number_parameters     229
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1276
_refine_ls_R_factor_gt           0.0547
_refine_ls_wR_factor_ref         0.1277
_refine_ls_wR_factor_gt          0.1079
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_restrained_S_all      1.009
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.39393(5) 0.69908(11) 0.35141(6) 0.0357(3) Uani 1 1 d . . . . .
S2 S 0.38474(6) 0.19184(11) 0.45635(7) 0.0459(3) Uani 1 1 d . . . . .
Cl1 Cl 0.03872(6) 0.82694(18) 0.14881(10) 0.0922(5) Uani 1 1 d . . . . .
O1 O 0.40564(13) 0.7927(3) 0.43780(17) 0.0434(7) Uani 1 1 d . . . . .
O2 O 0.44860(15) 0.7279(3) 0.29282(18) 0.0526(7) Uani 1 1 d . . . . .
N1 N 0.39801(15) 0.4856(3) 0.3721(2) 0.0342(7) Uani 1 1 d . . . . .
N2 N 0.30386(18) 0.4933(4) 0.4649(2) 0.0442(8) Uani 1 1 d . . . . .
C9 C 0.3558(2) 0.4086(4) 0.4340(2) 0.0322(8) Uani 1 1 d . . . . .
C10 C 0.2628(2) 0.4101(4) 0.5257(3) 0.0363(9) Uani 1 1 d . . . . .
C6 C 0.2692(2) 0.6943(4) 0.1936(3) 0.0420(10) Uani 1 1 d . . . . .
C1 C 0.2949(2) 0.7341(4) 0.2895(2) 0.0321(8) Uani 1 1 d . . . . .
C13 C 0.1765(2) 0.2665(4) 0.6489(3) 0.0468(10) Uani 1 1 d . . . . .
C2 C 0.2432(2) 0.8030(4) 0.3389(3) 0.0398(9) Uani 1 1 d . . . . .
H2 H 0.2630 0.8312 0.4019 0.048 Uiso 1 1 calc R U . . .
C11 C 0.2990(2) 0.3770(5) 0.6183(3) 0.0475(10) Uani 1 1 d . . . . .
H11 H 0.3528 0.4024 0.6405 0.057 Uiso 1 1 calc R U . . .
C7 C 0.4673(2) 0.3834(4) 0.3601(3) 0.0501(11) Uani 1 1 d . . . . .
H7A H 0.5149 0.4193 0.4057 0.060 Uiso 1 1 calc R U . . .
H7B H 0.4762 0.4001 0.2975 0.060 Uiso 1 1 calc R U . . .
C4 C 0.1384(2) 0.7959(5) 0.2051(3) 0.0534(11) Uani 1 1 d . . . . .
C8 C 0.4486(2) 0.1958(4) 0.3749(3) 0.0404(9) Uani 1 1 d . . . . .
H8A H 0.4973 0.1314 0.4002 0.048 Uiso 1 1 calc R U . . .
H8B H 0.4219 0.1427 0.3158 0.048 Uiso 1 1 calc R U . . .
C3 C 0.1632(2) 0.8329(4) 0.3001(3) 0.0456(10) Uani 1 1 d . . . . .
C12 C 0.2563(2) 0.3070(5) 0.6780(3) 0.0492(10) Uani 1 1 d . . . . .
H12 H 0.2821 0.2861 0.7403 0.059 Uiso 1 1 calc R U . . .
C16 C 0.3200(3) 0.6192(5) 0.1324(3) 0.0585(11) Uani 1 1 d . . . . .
H16A H 0.3496 0.7113 0.1114 0.088 Uiso 1 1 calc R U . . .
H16B H 0.2865 0.5630 0.0789 0.088 Uiso 1 1 calc R U . . .
H16C H 0.3563 0.5354 0.1676 0.088 Uiso 1 1 calc R U . . .
C5 C 0.1886(3) 0.7294(5) 0.1539(3) 0.0538(11) Uani 1 1 d . . . . .
H5 H 0.1686 0.7065 0.0903 0.065 Uiso 1 1 calc R U . . .
C15 C 0.1824(2) 0.3746(6) 0.4964(3) 0.0592(12) Uani 1 1 d . . . . .
H15 H 0.1558 0.3999 0.4349 0.071 Uiso 1 1 calc R U . . .
C14 C 0.1415(2) 0.3022(6) 0.5572(3) 0.0666(13) Uani 1 1 d . . . . .
H14 H 0.0876 0.2764 0.5351 0.080 Uiso 1 1 calc R U . . .
C17 C 0.1085(2) 0.8979(6) 0.3597(3) 0.0777(14) Uani 1 1 d . . . . .
H17A H 0.0706 0.9781 0.3238 0.117 Uiso 1 1 calc R U . . .
H17B H 0.1394 0.9563 0.4142 0.117 Uiso 1 1 calc R U . . .
H17C H 0.0808 0.8009 0.3791 0.117 Uiso 1 1 calc R U . . .
C18 C 0.1302(3) 0.1921(5) 0.7158(3) 0.0768(14) Uani 1 1 d . . . . .
H18A H 0.1663 0.1622 0.7740 0.115 Uiso 1 1 calc R U . . .
H18B H 0.1021 0.0893 0.6887 0.115 Uiso 1 1 calc R U . . .
H18C H 0.0926 0.2773 0.7272 0.115 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O1 1.425(2) . ?
S1 O2 1.427(3) . ?
S1 N1 1.661(3) . ?
S1 C1 1.758(3) . ?
S2 C9 1.742(3) . ?
S2 C8 1.795(4) . ?
Cl1 C4 1.742(4) . ?
N1 C9 1.412(4) . ?
N1 C7 1.470(4) . ?
N2 C9 1.269(4) . ?
N2 C10 1.407(4) . ?
C10 C11 1.378(5) . ?
C10 C15 1.379(5) . ?
C6 C5 1.403(5) . ?
C6 C1 1.404(5) . ?
C6 C16 1.500(5) . ?
C1 C2 1.373(5) . ?
C13 C14 1.365(5) . ?
C13 C12 1.377(5) . ?
C13 C18 1.508(5) . ?
C2 C3 1.384(5) . ?
C2 H2 0.9300 . ?
C11 C12 1.373(5) . ?
C11 H11 0.9300 . ?
C7 C8 1.499(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C4 C5 1.364(6) . ?
C4 C3 1.385(6) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C3 C17 1.505(5) . ?
C12 H12 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C5 H5 0.9300 . ?
C15 C14 1.371(5) . ?
C15 H15 0.9300 . ?
C14 H14 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S1 O2 118.33(15) . . ?
O1 S1 N1 110.03(14) . . ?
O2 S1 N1 104.76(14) . . ?
O1 S1 C1 107.62(15) . . ?
O2 S1 C1 111.30(16) . . ?
N1 S1 C1 103.85(14) . . ?
C9 S2 C8 92.97(16) . . ?
C9 N1 C7 113.9(3) . . ?
C9 N1 S1 121.4(2) . . ?
C7 N1 S1 120.3(2) . . ?
C9 N2 C10 119.4(3) . . ?
N2 C9 N1 121.6(3) . . ?
N2 C9 S2 127.9(3) . . ?
N1 C9 S2 110.5(2) . . ?
C11 C10 C15 117.7(4) . . ?
C11 C10 N2 121.5(3) . . ?
C15 C10 N2 120.5(4) . . ?
C5 C6 C1 115.3(4) . . ?
C5 C6 C16 118.9(4) . . ?
C1 C6 C16 125.8(3) . . ?
C2 C1 C6 121.0(3) . . ?
C2 C1 S1 117.2(3) . . ?
C6 C1 S1 121.8(3) . . ?
C14 C13 C12 116.4(4) . . ?
C14 C13 C18 122.1(4) . . ?
C12 C13 C18 121.5(4) . . ?
C1 C2 C3 123.6(4) . . ?
C1 C2 H2 118.2 . . ?
C3 C2 H2 118.2 . . ?
C12 C11 C10 120.6(4) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
N1 C7 C8 106.6(3) . . ?
N1 C7 H7A 110.4 . . ?
C8 C7 H7A 110.4 . . ?
N1 C7 H7B 110.4 . . ?
C8 C7 H7B 110.4 . . ?
H7A C7 H7B 108.6 . . ?
C5 C4 C3 122.5(4) . . ?
C5 C4 Cl1 118.1(3) . . ?
C3 C4 Cl1 119.3(4) . . ?
C7 C8 S2 107.2(2) . . ?
C7 C8 H8A 110.3 . . ?
S2 C8 H8A 110.3 . . ?
C7 C8 H8B 110.3 . . ?
S2 C8 H8B 110.3 . . ?
H8A C8 H8B 108.5 . . ?
C2 C3 C4 115.2(4) . . ?
C2 C3 C17 120.9(4) . . ?
C4 C3 C17 123.9(4) . . ?
C11 C12 C13 122.2(4) . . ?
C11 C12 H12 118.9 . . ?
C13 C12 H12 118.9 . . ?
C6 C16 H16A 109.5 . . ?
C6 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C6 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C4 C5 C6 122.4(4) . . ?
C4 C5 H5 118.8 . . ?
C6 C5 H5 118.8 . . ?
C14 C15 C10 120.4(4) . . ?
C14 C15 H15 119.8 . . ?
C10 C15 H15 119.8 . . ?
C13 C14 C15 122.6(4) . . ?
C13 C14 H14 118.7 . . ?
C15 C14 H14 118.7 . . ?
C3 C17 H17A 109.5 . . ?
C3 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C3 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C13 C18 H18A 109.5 . . ?
C13 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C13 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

_refine_diff_density_max         0.299
_refine_diff_density_min         -0.334
_refine_diff_density_rms         0.061


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
