# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_z
_database_code_depnum_ccdc_archive 'CCDC 1058034'
_audit_update_record             
;
2015-04-06 deposited with the CCDC.
2015-09-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H16 Cl N O2 S2'
_chemical_formula_weight         353.87

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   P2(1)/n

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

_cell_length_a                   12.739(5)
_cell_length_b                   5.382(2)
_cell_length_c                   24.848(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.362(6)
_cell_angle_gamma                90.00
_cell_volume                     1657.3(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    1214
_cell_measurement_theta_min      2.68
_cell_measurement_theta_max      19.89

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.418
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             736
_exptl_absorpt_coefficient_mu    0.488
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9304
_exptl_absorpt_correction_T_max  0.9529
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         none
_diffrn_standards_interval_count 'not measured'
_diffrn_standards_interval_time  'not measured'
_diffrn_standards_decay_%        none
_diffrn_reflns_number            8017
_diffrn_reflns_av_R_equivalents  0.0543
_diffrn_reflns_av_sigmaI/netI    0.0722
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.66
_diffrn_reflns_theta_max         25.11
_reflns_number_total             2935
_reflns_number_gt                1827
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SMART'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.0619P)²+0.0716P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2935
_refine_ls_number_parameters     201
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1157
_refine_ls_R_factor_gt           0.0636
_refine_ls_wR_factor_ref         0.1423
_refine_ls_wR_factor_gt          0.1236
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.37965(11) 0.5731(3) -0.13587(5) 0.0840(5) Uani 1 1 d . . .
N1 N 0.8059(2) 0.4907(5) 0.02038(12) 0.0377(8) Uani 1 1 d . . .
O1 O 0.7617(2) 0.8210(5) 0.06742(11) 0.0498(8) Uani 1 1 d . . .
O2 O 0.8523(2) 0.1680(5) -0.02853(12) 0.0526(8) Uani 1 1 d . . .
S1 S 0.86537(9) 1.00627(18) 0.16463(4) 0.0453(3) Uani 1 1 d . . .
S2 S 1.08274(9) 0.7594(2) 0.19805(5) 0.0581(4) Uani 1 1 d . . .
C1 C 0.6258(3) 0.3269(7) -0.01848(17) 0.0462(11) Uani 1 1 d . . .
H1 H 0.6402 0.1945 0.0062 0.055 Uiso 1 1 calc R . .
C2 C 0.5263(3) 0.3451(8) -0.05553(18) 0.0524(12) Uani 1 1 d . . .
H2 H 0.4738 0.2244 -0.0561 0.063 Uiso 1 1 calc R . .
C3 C 0.5058(3) 0.5431(8) -0.09156(17) 0.0499(11) Uani 1 1 d . . .
C4 C 0.5815(4) 0.7229(8) -0.09244(18) 0.0568(12) Uani 1 1 d . . .
C5 C 0.6812(4) 0.7012(7) -0.05567(18) 0.0534(12) Uani 1 1 d . . .
H5 H 0.7341 0.8197 -0.0561 0.064 Uiso 1 1 calc R . .
C6 C 0.7032(3) 0.5063(7) -0.01841(16) 0.0403(10) Uani 1 1 d . . .
C7 C 0.8281(3) 0.6612(7) 0.06447(16) 0.0374(9) Uani 1 1 d . . .
C8 C 0.9317(3) 0.6376(6) 0.10413(16) 0.0367(9) Uani 1 1 d . . .
C9 C 1.0042(3) 0.4454(7) 0.09465(17) 0.0457(11) Uani 1 1 d . . .
H9 H 1.0706 0.4278 0.1195 0.055 Uiso 1 1 calc R . .
C10 C 0.9795(3) 0.2923(7) 0.05153(18) 0.0436(10) Uani 1 1 d . . .
H10 H 1.0294 0.1722 0.0472 0.052 Uiso 1 1 calc R . .
C11 C 0.8781(3) 0.3057(7) 0.01120(18) 0.0409(10) Uani 1 1 d . . .
C12 C 0.9560(3) 0.7901(7) 0.14963(16) 0.0408(10) Uani 1 1 d . . .
C13 C 0.9357(4) 1.1515(8) 0.22866(17) 0.0559(12) Uani 1 1 d . . .
H13A H 0.9535 1.0285 0.2579 0.067 Uiso 1 1 calc R . .
H13B H 1.0021 1.2274 0.2240 0.067 Uiso 1 1 calc R . .
C14 C 0.8614(4) 1.3478(8) 0.24339(18) 0.0630(13) Uani 1 1 d . . .
H14A H 0.8461 1.4712 0.2147 0.094 Uiso 1 1 calc R . .
H14B H 0.8958 1.4250 0.2778 0.094 Uiso 1 1 calc R . .
H14C H 0.7952 1.2714 0.2470 0.094 Uiso 1 1 calc R . .
C15 C 1.1782(4) 0.8830(11) 0.1611(2) 0.0789(16) Uani 1 1 d . . .
H15A H 1.1532 0.8479 0.1220 0.095 Uiso 1 1 calc R . .
H15B H 1.1829 1.0619 0.1658 0.095 Uiso 1 1 calc R . .
C16 C 1.2859(4) 0.7720(12) 0.1818(3) 0.109(2) Uani 1 1 d . . .
H16A H 1.3086 0.7976 0.2210 0.163 Uiso 1 1 calc R . .
H16B H 1.3365 0.8491 0.1638 0.163 Uiso 1 1 calc R . .
H16C H 1.2826 0.5970 0.1741 0.163 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
Cl1 C3 1.733(4) . ?
N1 C7 1.407(4) . ?
N1 C11 1.410(4) . ?
N1 C6 1.436(5) . ?
O1 C7 1.220(4) . ?
O2 C11 1.217(4) . ?
S1 C12 1.739(4) . ?
S1 C13 1.813(4) . ?
S2 C12 1.784(4) . ?
S2 C15 1.811(5) . ?
C1 C6 1.380(5) . ?
C1 C2 1.387(5) . ?
C1 H1 0.9300 . ?
C2 C3 1.377(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.370(6) . ?
C4 C5 1.387(6) . ?
C5 C6 1.384(5) . ?
C5 H5 0.9300 . ?
C7 C8 1.459(5) . ?
C8 C12 1.373(5) . ?
C8 C9 1.442(5) . ?
C9 C10 1.330(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.442(5) . ?
C10 H10 0.9300 . ?
C13 C14 1.519(5) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C16 1.475(7) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 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
C7 N1 C11 124.4(3) . . ?
C7 N1 C6 118.2(3) . . ?
C11 N1 C6 117.4(3) . . ?
C12 S1 C13 104.99(19) . . ?
C12 S2 C15 103.5(2) . . ?
C6 C1 C2 119.6(4) . . ?
C6 C1 H1 120.2 . . ?
C2 C1 H1 120.2 . . ?
C3 C2 C1 119.6(4) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C4 C3 C2 121.9(4) . . ?
C4 C3 Cl1 118.5(3) . . ?
C2 C3 Cl1 119.6(3) . . ?
C3 C4 C5 118.1(4) . . ?
C6 C5 C4 121.2(4) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C1 C6 C5 119.6(4) . . ?
C1 C6 N1 120.0(4) . . ?
C5 C6 N1 120.4(3) . . ?
O1 C7 N1 119.3(4) . . ?
O1 C7 C8 123.5(3) . . ?
N1 C7 C8 117.2(3) . . ?
C12 C8 C9 122.1(4) . . ?
C12 C8 C7 120.1(3) . . ?
C9 C8 C7 117.8(4) . . ?
C10 C9 C8 122.3(4) . . ?
C10 C9 H9 118.9 . . ?
C8 C9 H9 118.9 . . ?
C9 C10 C11 122.5(3) . . ?
C9 C10 H10 118.8 . . ?
C11 C10 H10 118.8 . . ?
O2 C11 N1 119.8(4) . . ?
O2 C11 C10 124.3(3) . . ?
N1 C11 C10 115.8(4) . . ?
C8 C12 S1 122.8(3) . . ?
C8 C12 S2 119.8(3) . . ?
S1 C12 S2 117.4(2) . . ?
C14 C13 S1 107.6(3) . . ?
C14 C13 H13A 110.2 . . ?
S1 C13 H13A 110.2 . . ?
C14 C13 H13B 110.2 . . ?
S1 C13 H13B 110.2 . . ?
H13A C13 H13B 108.5 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 S2 110.7(4) . . ?
C16 C15 H15A 109.5 . . ?
S2 C15 H15A 109.5 . . ?
C16 C15 H15B 109.5 . . ?
S2 C15 H15B 109.5 . . ?
H15A C15 H15B 108.1 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        25.11
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.456
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.058
