# Electronic Supplementary Material (ESI) for ChemComm.
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1522821'
_audit_update_record             
;
2016-12-15 deposited with the CCDC.
2017-03-13 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT906_shelx               
;
PROBLEM: Large K value in the Analysis of Variance ......      2.041 Check
RESPONSE: The most common place for a high value of K is in the lowest-intensity bin in the table. Almost all area detector integration programs end up slightly underestimating the background, resulting in overestimated values of Fo, thus the high value of Fo/Fc. This is most obvious in the weakest intensities, since the small addition to Fo becomes insignificant in the ratio when Fo is large.
;
# Added during the CSD deposition process: Thursday 15 December 2016 01:31 AM
# end Validation Reply Form


_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 4-Benzoyl-5H-1,2,3-dithiazol-5-one, low-temperature polymorph
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H5 N O2 S2'
_chemical_formula_sum            'C9 H5 N O2 S2'
_chemical_formula_weight         223.26

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

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

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

_cell_length_a                   7.17006(6)
_cell_length_b                   11.34032(10)
_cell_length_c                   22.9044(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1862.37(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(1)
_cell_measurement_reflns_used    27594
_cell_measurement_theta_min      3.8670
_cell_measurement_theta_max      76.8390

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.593
_exptl_crystal_F_000             912
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    4.954
_shelx_estimated_absorpt_T_min   0.276
_shelx_estimated_absorpt_T_max   0.469
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.036
_exptl_absorpt_correction_T_max  0.350
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;

_exptl_special_details           
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;

_diffrn_ambient_temperature      150(1)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.3693
_diffrn_reflns_number            45244
_diffrn_reflns_av_unetI/netI     0.0157
_diffrn_reflns_av_R_equivalents  0.0657
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         3.860
_diffrn_reflns_theta_max         76.869
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1956
_reflns_number_gt                1953
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_structure_solution    SHELXS
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0520P)²+0.9593P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1956
_refine_ls_number_parameters     142
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0350
_refine_ls_R_factor_gt           0.0349
_refine_ls_wR_factor_ref         0.0954
_refine_ls_wR_factor_gt          0.0954
_refine_ls_goodness_of_fit_ref   1.139
_refine_ls_restrained_S_all      1.139
_refine_ls_shift/su_max          0.001
_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 0.23202(6) 0.45767(4) 0.01850(2) 0.03227(15) Uani 1 1 d . . . . .
S2 S 0.36592(6) 0.54743(3) 0.08350(2) 0.03117(15) Uani 1 1 d . . . . .
N3 N 0.4971(2) 0.44086(12) 0.10766(7) 0.0293(3) Uani 1 1 d . . . . .
C4 C 0.4858(2) 0.33878(14) 0.08222(7) 0.0269(3) Uani 1 1 d . . . . .
C5 C 0.3535(2) 0.32171(15) 0.03304(7) 0.0287(3) Uani 1 1 d . . . . .
O6 O 0.32365(19) 0.23330(11) 0.00487(6) 0.0355(3) Uani 1 1 d . . . . .
C7 C 0.5984(2) 0.23697(15) 0.10499(7) 0.0286(3) Uani 1 1 d . . . . .
O8 O 0.54143(19) 0.13708(10) 0.09680(6) 0.0372(3) Uani 1 1 d . . . . .
C9 C 0.7723(2) 0.25936(15) 0.13874(7) 0.0276(3) Uani 1 1 d . . . . .
C10 C 0.8366(3) 0.16854(16) 0.17512(7) 0.0306(4) Uani 1 1 d . . . . .
H10 H 0.766(3) 0.098(2) 0.1771(10) 0.037 Uiso 1 1 d . U . . .
C11 C 0.9968(3) 0.18376(17) 0.20797(8) 0.0369(4) Uani 1 1 d . . . . .
H11 H 1.034(3) 0.125(2) 0.2332(11) 0.044 Uiso 1 1 d . U . . .
C12 C 1.0951(3) 0.28907(18) 0.20506(9) 0.0397(4) Uani 1 1 d . . . . .
H12 H 1.207(4) 0.300(2) 0.2273(11) 0.048 Uiso 1 1 d . U . . .
C13 C 1.0342(3) 0.37837(18) 0.16841(9) 0.0376(4) Uani 1 1 d . . . . .
H13 H 1.100(3) 0.452(2) 0.1669(11) 0.045 Uiso 1 1 d . U . . .
C14 C 0.8744(2) 0.36391(16) 0.13498(8) 0.0316(4) Uani 1 1 d . . . . .
H14 H 0.839(3) 0.425(2) 0.1095(10) 0.038 Uiso 1 1 d . 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 C5 1.8017(17) . ?
S1 S2 2.0432(6) . ?
S2 N3 1.6284(15) . ?
N3 C4 1.298(2) . ?
C4 C5 1.485(2) . ?
C4 C7 1.502(2) . ?
C5 O6 1.211(2) . ?
C7 O8 1.219(2) . ?
C7 C9 1.489(2) . ?
C9 C14 1.396(2) . ?
C9 C10 1.403(2) . ?
C10 C11 1.384(3) . ?
C10 H10 0.95(2) . ?
C11 C12 1.388(3) . ?
C11 H11 0.92(2) . ?
C12 C13 1.386(3) . ?
C12 H12 0.96(3) . ?
C13 C14 1.388(3) . ?
C13 H13 0.95(2) . ?
C14 H14 0.94(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 S1 S2 93.70(6) . . ?
N3 S2 S1 98.59(6) . . ?
C4 N3 S2 118.22(13) . . ?
N3 C4 C5 119.77(15) . . ?
N3 C4 C7 119.72(15) . . ?
C5 C4 C7 120.42(14) . . ?
O6 C5 C4 128.65(16) . . ?
O6 C5 S1 121.64(13) . . ?
C4 C5 S1 109.71(12) . . ?
O8 C7 C9 121.27(16) . . ?
O8 C7 C4 118.74(16) . . ?
C9 C7 C4 119.95(14) . . ?
C14 C9 C10 119.20(16) . . ?
C14 C9 C7 123.50(15) . . ?
C10 C9 C7 117.28(15) . . ?
C11 C10 C9 120.27(17) . . ?
C11 C10 H10 121.6(14) . . ?
C9 C10 H10 118.1(14) . . ?
C10 C11 C12 120.18(17) . . ?
C10 C11 H11 119.5(15) . . ?
C12 C11 H11 120.3(14) . . ?
C13 C12 C11 119.85(18) . . ?
C13 C12 H12 119.3(14) . . ?
C11 C12 H12 120.9(14) . . ?
C12 C13 C14 120.52(19) . . ?
C12 C13 H13 120.2(15) . . ?
C14 C13 H13 119.3(15) . . ?
C13 C14 C9 119.95(17) . . ?
C13 C14 H14 118.4(14) . . ?
C9 C14 H14 121.6(14) . . ?

_refine_diff_density_max         0.322
_refine_diff_density_min         -0.417
_refine_diff_density_rms         0.062

_shelxl_version_number           2013-4


_exptl_crystal_recrystallization_method Sublimation
####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1522822'
_audit_update_record             
;
2016-12-15 deposited with the CCDC.
2017-03-13 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT906_shelx               
;
PROBLEM: Large K value in the Analysis of Variance ......      2.321 Check
RESPONSE: The most common place for a high value of K is in the lowest-intensity bin in the table. Almost all area detector integration programs end up slightly underestimating the background, resulting in overestimated values of Fo, thus the high value of Fo/Fc. This is most obvious in the weakest intensities, since the small addition to Fo becomes insignificant in the ratio when Fo is large.
;
# Added during the CSD deposition process: Thursday 15 December 2016 01:31 AM
# end Validation Reply Form


_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 4-Benzoyl-5H-1,2,3-dithiazol-5-one, low-temperature polymorph
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H5 N O2 S2'
_chemical_formula_sum            'C9 H5 N O2 S2'
_chemical_formula_weight         223.26

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

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

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

_cell_length_a                   7.20370(19)
_cell_length_b                   11.4142(3)
_cell_length_c                   23.2130(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1908.68(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6021
_cell_measurement_theta_min      3.7570
_cell_measurement_theta_max      74.2230

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.554
_exptl_crystal_F_000             912
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    4.834
_shelx_estimated_absorpt_T_min   0.445
_shelx_estimated_absorpt_T_max   0.830
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.40583
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.3693
_diffrn_reflns_number            15695
_diffrn_reflns_av_unetI/netI     0.0172
_diffrn_reflns_av_R_equivalents  0.0402
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         3.808
_diffrn_reflns_theta_max         74.441
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             1937
_reflns_number_gt                1664
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_structure_solution    SHELXS
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0409P)²+1.8641P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1937
_refine_ls_number_parameters     142
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0506
_refine_ls_R_factor_gt           0.0417
_refine_ls_wR_factor_ref         0.1068
_refine_ls_wR_factor_gt          0.1017
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_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 0.23385(10) 0.45570(6) 0.01939(3) 0.0534(2) Uani 1 1 d . . . . .
S2 S 0.36648(9) 0.54491(5) 0.08334(3) 0.0512(2) Uani 1 1 d . . . . .
N3 N 0.4971(3) 0.43900(18) 0.10715(9) 0.0457(5) Uani 1 1 d . . . . .
C4 C 0.4862(3) 0.3378(2) 0.08217(10) 0.0408(5) Uani 1 1 d . . . . .
C5 C 0.3551(3) 0.3206(2) 0.03364(10) 0.0437(5) Uani 1 1 d . . . . .
O6 O 0.3269(3) 0.23322(16) 0.00591(8) 0.0588(5) Uani 1 1 d . . . . .
C7 C 0.5978(3) 0.2370(2) 0.10493(10) 0.0436(5) Uani 1 1 d . . . . .
O8 O 0.5408(3) 0.13790(16) 0.09677(10) 0.0645(6) Uani 1 1 d . . . . .
C9 C 0.7707(3) 0.2587(2) 0.13862(10) 0.0415(5) Uani 1 1 d . . . . .
C10 C 0.8327(4) 0.1689(2) 0.17468(11) 0.0495(6) Uani 1 1 d . . . . .
H10 H 0.765(4) 0.100(3) 0.1768(13) 0.059 Uiso 1 1 d . U . . .
C11 C 0.9924(5) 0.1840(3) 0.20705(13) 0.0642(8) Uani 1 1 d . . . . .
H11 H 1.023(5) 0.126(3) 0.2313(15) 0.077 Uiso 1 1 d . U . . .
C12 C 1.0898(5) 0.2874(3) 0.20399(14) 0.0670(8) Uani 1 1 d . . . . .
H12 H 1.203(5) 0.300(3) 0.2259(15) 0.080 Uiso 1 1 d . U . . .
C13 C 1.0325(4) 0.3755(3) 0.16771(14) 0.0620(7) Uani 1 1 d . . . . .
H13 H 1.101(5) 0.454(3) 0.1663(15) 0.074 Uiso 1 1 d . U . . .
C14 C 0.8730(4) 0.3614(2) 0.13461(12) 0.0498(6) Uani 1 1 d . . . . .
H14 H 0.840(4) 0.426(3) 0.1092(13) 0.060 Uiso 1 1 d . 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 C5 1.803(3) . ?
S1 S2 2.0379(9) . ?
S2 N3 1.629(2) . ?
N3 C4 1.295(3) . ?
C4 C5 1.483(3) . ?
C4 C7 1.499(3) . ?
C5 O6 1.205(3) . ?
C7 O8 1.218(3) . ?
C7 C9 1.492(3) . ?
C9 C14 1.387(4) . ?
C9 C10 1.397(3) . ?
C10 C11 1.385(4) . ?
C10 H10 0.93(3) . ?
C11 C12 1.375(5) . ?
C11 H11 0.89(3) . ?
C12 C13 1.375(4) . ?
C12 H12 0.97(4) . ?
C13 C14 1.391(4) . ?
C13 H13 1.02(3) . ?
C14 H14 0.97(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 S1 S2 93.82(8) . . ?
N3 S2 S1 98.47(8) . . ?
C4 N3 S2 118.38(18) . . ?
N3 C4 C5 119.8(2) . . ?
N3 C4 C7 119.6(2) . . ?
C5 C4 C7 120.5(2) . . ?
O6 C5 C4 128.5(2) . . ?
O6 C5 S1 121.9(2) . . ?
C4 C5 S1 109.58(17) . . ?
O8 C7 C9 121.1(2) . . ?
O8 C7 C4 118.5(2) . . ?
C9 C7 C4 120.3(2) . . ?
C14 C9 C10 119.4(2) . . ?
C14 C9 C7 123.3(2) . . ?
C10 C9 C7 117.3(2) . . ?
C11 C10 C9 119.9(3) . . ?
C11 C10 H10 121.0(19) . . ?
C9 C10 H10 119(2) . . ?
C12 C11 C10 120.2(3) . . ?
C12 C11 H11 123(2) . . ?
C10 C11 H11 117(2) . . ?
C13 C12 C11 120.4(3) . . ?
C13 C12 H12 117(2) . . ?
C11 C12 H12 122(2) . . ?
C12 C13 C14 120.1(3) . . ?
C12 C13 H13 121(2) . . ?
C14 C13 H13 118.9(19) . . ?
C9 C14 C13 119.9(3) . . ?
C9 C14 H14 123.5(18) . . ?
C13 C14 H14 116.5(18) . . ?

_refine_diff_density_max         0.269
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.050

_shelxl_version_number           2013-4


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: THF/hexane'
####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1522823'
_audit_update_record             
;
2016-12-15 deposited with the CCDC.
2017-03-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 4-Benzoyl-5H-1,2,3-dithiazol-5-one, high-temperature polymorph
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H5 N O2 S2'
_chemical_formula_sum            'C9 H5 N O2 S2'
_chemical_formula_weight         223.26

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

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

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

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

_cell_length_a                   7.99603(12)
_cell_length_b                   10.01680(13)
_cell_length_c                   11.32452(15)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     907.03(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(1)
_cell_measurement_reflns_used    12701
_cell_measurement_theta_min      3.9030
_cell_measurement_theta_max      75.9510

_exptl_crystal_description       shapeless
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.635
_exptl_crystal_F_000             456
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    5.086
_shelx_estimated_absorpt_T_min   0.208
_shelx_estimated_absorpt_T_max   0.630
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.11993
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      150(1)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.3693
_diffrn_reflns_number            17711
_diffrn_reflns_av_unetI/netI     0.0135
_diffrn_reflns_av_R_equivalents  0.0347
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         5.898
_diffrn_reflns_theta_max         76.829
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1911
_reflns_number_gt                1905
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.697
_reflns_Friedel_fraction_max     0.996
_reflns_Friedel_fraction_full    1.000

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

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_structure_solution    SHELXS
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0394P)²+0.2038P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 782 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.005(6)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         1911
_refine_ls_number_parameters     142
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0229
_refine_ls_R_factor_gt           0.0228
_refine_ls_wR_factor_ref         0.0625
_refine_ls_wR_factor_gt          0.0625
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_restrained_S_all      1.073
_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 0.35630(8) -0.02467(5) 0.65386(5) 0.03445(15) Uani 1 1 d . . . . .
S2 S 0.47349(7) 0.12288(5) 0.74583(5) 0.03342(15) Uani 1 1 d . . . . .
N3 N 0.4702(2) 0.23945(18) 0.64465(15) 0.0292(4) Uani 1 1 d . . . . .
C4 C 0.4064(2) 0.20929(19) 0.54326(18) 0.0237(4) Uani 1 1 d . . . . .
C5 C 0.3368(3) 0.0747(2) 0.52189(19) 0.0295(4) Uani 1 1 d . . . . .
O6 O 0.2712(3) 0.03397(18) 0.43344(16) 0.0485(5) Uani 1 1 d . . . . .
C7 C 0.4151(3) 0.3090(2) 0.44318(18) 0.0264(4) Uani 1 1 d . . . . .
O8 O 0.4787(3) 0.27295(17) 0.35092(15) 0.0433(4) Uani 1 1 d . . . . .
C9 C 0.3493(2) 0.44555(18) 0.46177(17) 0.0221(4) Uani 1 1 d . . . . .
C10 C 0.3875(2) 0.5444(2) 0.37867(18) 0.0256(4) Uani 1 1 d . . . . .
H10 H 0.459(3) 0.519(3) 0.314(2) 0.031 Uiso 1 1 d . U . . .
C11 C 0.3236(3) 0.6713(2) 0.39124(19) 0.0270(4) Uani 1 1 d . . . . .
H11 H 0.349(3) 0.740(3) 0.341(2) 0.032 Uiso 1 1 d . U . . .
C12 C 0.2196(3) 0.7012(2) 0.48672(19) 0.0281(4) Uani 1 1 d . . . . .
H12 H 0.175(3) 0.792(3) 0.494(3) 0.034 Uiso 1 1 d . U . . .
C13 C 0.1812(3) 0.6038(2) 0.56935(19) 0.0273(4) Uani 1 1 d . . . . .
H13 H 0.112(3) 0.624(3) 0.634(2) 0.033 Uiso 1 1 d . U . . .
C14 C 0.2461(2) 0.4759(2) 0.55781(17) 0.0232(4) Uani 1 1 d . . . . .
H14 H 0.214(3) 0.407(3) 0.611(2) 0.028 Uiso 1 1 d . 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 C5 1.802(2) . ?
S1 S2 2.0365(8) . ?
S2 N3 1.6362(18) . ?
N3 C4 1.292(3) . ?
C4 C5 1.479(3) . ?
C4 C7 1.512(3) . ?
C5 O6 1.202(3) . ?
C7 O8 1.217(3) . ?
C7 C9 1.480(3) . ?
C9 C14 1.399(3) . ?
C9 C10 1.400(3) . ?
C10 C11 1.377(3) . ?
C10 H10 0.96(3) . ?
C11 C12 1.397(3) . ?
C11 H11 0.92(3) . ?
C12 C13 1.387(3) . ?
C12 H12 0.98(3) . ?
C13 C14 1.388(3) . ?
C13 H13 0.94(3) . ?
C14 H14 0.95(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 S1 S2 93.62(7) . . ?
N3 S2 S1 98.77(7) . . ?
C4 N3 S2 117.50(16) . . ?
N3 C4 C5 120.48(18) . . ?
N3 C4 C7 119.57(18) . . ?
C5 C4 C7 119.79(17) . . ?
O6 C5 C4 127.6(2) . . ?
O6 C5 S1 122.78(17) . . ?
C4 C5 S1 109.58(15) . . ?
O8 C7 C9 123.02(19) . . ?
O8 C7 C4 117.80(18) . . ?
C9 C7 C4 119.18(16) . . ?
C14 C9 C10 119.85(18) . . ?
C14 C9 C7 121.40(17) . . ?
C10 C9 C7 118.72(17) . . ?
C11 C10 C9 120.15(18) . . ?
C11 C10 H10 122.7(18) . . ?
C9 C10 H10 117.2(17) . . ?
C10 C11 C12 119.95(19) . . ?
C10 C11 H11 123.4(17) . . ?
C12 C11 H11 116.6(17) . . ?
C13 C12 C11 120.20(19) . . ?
C13 C12 H12 121.2(17) . . ?
C11 C12 H12 118.6(17) . . ?
C12 C13 C14 120.21(19) . . ?
C12 C13 H13 120.2(17) . . ?
C14 C13 H13 119.6(17) . . ?
C13 C14 C9 119.64(18) . . ?
C13 C14 H14 120.5(16) . . ?
C9 C14 H14 119.7(16) . . ?

_refine_diff_density_max         0.182
_refine_diff_density_min         -0.308
_refine_diff_density_rms         0.040

_shelxl_version_number           2013-4


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Chlorobenzene'
####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1522824'
_audit_update_record             
;
2016-12-15 deposited with the CCDC.
2017-03-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 4-Benzoyl-5H-1,2,3-dithiazol-5-one, high-temperature polymorph
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H5 N O2 S2'
_chemical_formula_sum            'C9 H5 N O2 S2'
_chemical_formula_weight         223.26

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

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

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

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

_cell_length_a                   8.23838(12)
_cell_length_b                   10.03744(12)
_cell_length_c                   11.30577(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     934.90(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    11629
_cell_measurement_theta_min      3.8890
_cell_measurement_theta_max      76.4110

_exptl_crystal_description       shapeless
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.586
_exptl_crystal_F_000             456
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    4.935
_shelx_estimated_absorpt_T_min   0.215
_shelx_estimated_absorpt_T_max   0.638
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.04600
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.3693
_diffrn_reflns_number            17588
_diffrn_reflns_av_unetI/netI     0.0138
_diffrn_reflns_av_R_equivalents  0.0360
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         5.895
_diffrn_reflns_theta_max         76.735
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1974
_reflns_number_gt                1944
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.697
_reflns_Friedel_fraction_max     0.994
_reflns_Friedel_fraction_full    1.000

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

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_structure_solution    SHELXS
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0399P)²+0.1992P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 794 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.003(7)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         1974
_refine_ls_number_parameters     142
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0304
_refine_ls_R_factor_gt           0.0299
_refine_ls_wR_factor_ref         0.0808
_refine_ls_wR_factor_gt          0.0801
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.064
_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 0.35689(13) -0.02337(8) 0.65403(7) 0.0749(3) Uani 1 1 d . . . . .
S2 S 0.47186(11) 0.12146(9) 0.74607(7) 0.0724(2) Uani 1 1 d . . . . .
N3 N 0.4698(3) 0.2387(3) 0.6454(2) 0.0620(6) Uani 1 1 d . . . . .
C4 C 0.4083(3) 0.2097(3) 0.5443(2) 0.0502(6) Uani 1 1 d . . . . .
C5 C 0.3392(4) 0.0766(3) 0.5231(2) 0.0613(7) Uani 1 1 d . . . . .
O6 O 0.2754(5) 0.0370(3) 0.4348(2) 0.1025(10) Uani 1 1 d . . . . .
C7 C 0.4176(4) 0.3098(3) 0.4447(2) 0.0563(6) Uani 1 1 d . . . . .
O8 O 0.4819(4) 0.2746(3) 0.3533(2) 0.0928(9) Uani 1 1 d . . . . .
C9 C 0.3523(3) 0.4453(2) 0.4624(2) 0.0458(5) Uani 1 1 d . . . . .
C10 C 0.3908(3) 0.5441(3) 0.3805(2) 0.0555(6) Uani 1 1 d . . . . .
H10 H 0.463(4) 0.517(4) 0.318(3) 0.067 Uiso 1 1 d . U . . .
C11 C 0.3274(4) 0.6699(3) 0.3924(3) 0.0577(6) Uani 1 1 d . . . . .
H11 H 0.357(4) 0.742(4) 0.340(3) 0.069 Uiso 1 1 d . U . . .
C12 C 0.2235(4) 0.6987(3) 0.4859(3) 0.0606(7) Uani 1 1 d . . . . .
H12 H 0.179(4) 0.791(3) 0.494(3) 0.073 Uiso 1 1 d . U . . .
C13 C 0.1851(4) 0.6013(3) 0.5670(3) 0.0584(6) Uani 1 1 d . . . . .
H13 H 0.117(4) 0.619(3) 0.628(3) 0.070 Uiso 1 1 d . U . . .
C14 C 0.2493(3) 0.4747(3) 0.5565(2) 0.0492(5) Uani 1 1 d . . . . .
H14 H 0.218(4) 0.409(3) 0.609(3) 0.059 Uiso 1 1 d . 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 C5 1.795(3) . ?
S1 S2 2.0231(12) . ?
S2 N3 1.637(2) . ?
N3 C4 1.284(3) . ?
C4 C5 1.472(4) . ?
C4 C7 1.511(3) . ?
C5 O6 1.196(4) . ?
C7 O8 1.213(3) . ?
C7 C9 1.476(4) . ?
C9 C14 1.392(3) . ?
C9 C10 1.394(3) . ?
C10 C11 1.373(4) . ?
C10 H10 0.96(3) . ?
C11 C12 1.390(5) . ?
C11 H11 0.97(3) . ?
C12 C13 1.378(4) . ?
C12 H12 1.00(3) . ?
C13 C14 1.381(4) . ?
C13 H13 0.91(3) . ?
C14 H14 0.93(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 S1 S2 93.47(10) . . ?
N3 S2 S1 98.85(9) . . ?
C4 N3 S2 117.4(2) . . ?
N3 C4 C5 120.2(2) . . ?
N3 C4 C7 119.5(2) . . ?
C5 C4 C7 120.1(2) . . ?
O6 C5 C4 127.5(3) . . ?
O6 C5 S1 122.5(2) . . ?
C4 C5 S1 109.98(19) . . ?
O8 C7 C9 122.9(3) . . ?
O8 C7 C4 117.6(2) . . ?
C9 C7 C4 119.5(2) . . ?
C14 C9 C10 119.7(2) . . ?
C14 C9 C7 121.4(2) . . ?
C10 C9 C7 118.9(2) . . ?
C11 C10 C9 120.2(3) . . ?
C11 C10 H10 125(2) . . ?
C9 C10 H10 115(2) . . ?
C10 C11 C12 120.0(3) . . ?
C10 C11 H11 122(2) . . ?
C12 C11 H11 118(2) . . ?
C13 C12 C11 119.9(3) . . ?
C13 C12 H12 121(2) . . ?
C11 C12 H12 119(2) . . ?
C12 C13 C14 120.6(3) . . ?
C12 C13 H13 120(2) . . ?
C14 C13 H13 119(2) . . ?
C13 C14 C9 119.6(2) . . ?
C13 C14 H14 119.8(19) . . ?
C9 C14 H14 121(2) . . ?

_refine_diff_density_max         0.108
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.035

_shelxl_version_number           2013-4


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Chlorobenzene'
