# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_BD31M
_database_code_depnum_ccdc_archive 'CCDC 1561129'
_audit_update_record             
;
2017-07-10 deposited with the CCDC.
2017-10-09 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         'C15 H17 Cl O S2'
_chemical_formula_sum            'C15 H17 Cl O S2'
_chemical_formula_weight         312.86

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'
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   5.8350(4)
_cell_length_b                   8.6412(6)
_cell_length_c                   15.4578(10)
_cell_angle_alpha                85.6620(10)
_cell_angle_beta                 83.5850(10)
_cell_angle_gamma                86.6520(10)
_cell_volume                     771.32(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5082
_cell_measurement_theta_min      2.37
_cell_measurement_theta_max      28.12

_exptl_crystal_description       Needle
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_F_000             328
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.508
_shelx_estimated_absorpt_T_min   0.823
_shelx_estimated_absorpt_T_max   0.951
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.874
_exptl_absorpt_correction_T_max  0.950
_exptl_absorpt_process_details   'Bruker AXS SADABS program'
_exptl_absorpt_special_details   
'Sheldrick,G.M.,(2003),University of gottingen,Germany'
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7421
_diffrn_reflns_av_unetI/netI     0.0146
_diffrn_reflns_av_R_equivalents  0.0145
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.367
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2701
_reflns_number_gt                2461
_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_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)+(0.0550P)²+0.2500P] 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         2701
_refine_ls_number_parameters     175
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0404
_refine_ls_R_factor_gt           0.0376
_refine_ls_wR_factor_ref         0.1066
_refine_ls_wR_factor_gt          0.1039
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.070
_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
C1 C -0.2598(5) 0.0628(4) 0.41296(19) 0.0889(8) Uani 1 1 d . . . . .
H1A H -0.2265 0.1099 0.4642 0.133 Uiso 1 1 calc R U . . .
H1B H -0.3408 -0.0301 0.4299 0.133 Uiso 1 1 calc R U . . .
H1C H -0.3538 0.1342 0.3797 0.133 Uiso 1 1 calc R U . . .
C2 C 0.1184(3) 0.1981(2) 0.31318(13) 0.0541(5) Uani 1 1 d . . . . .
C3 C 0.1887(4) 0.2294(2) 0.22923(13) 0.0529(5) Uani 1 1 d . . . . .
C4 C 0.3286(5) 0.3654(3) 0.19327(14) 0.0701(6) Uani 1 1 d . . . . .
H4A H 0.2316 0.4388 0.1612 0.084 Uiso 1 1 calc R U . . .
H4B H 0.4548 0.3288 0.1524 0.084 Uiso 1 1 calc R U . . .
C5 C 0.4277(4) 0.4498(3) 0.26259(14) 0.0627(5) Uani 1 1 d . . . . .
H5A H 0.5492 0.3837 0.2862 0.075 Uiso 1 1 calc R U . . .
H5B H 0.4967 0.5433 0.2353 0.075 Uiso 1 1 calc R U . . .
C6 C 0.2490(4) 0.4943(2) 0.33728(13) 0.0543(5) Uani 1 1 d . . . . .
C7 C 0.0446(5) 0.5879(3) 0.3045(2) 0.0875(8) Uani 1 1 d . . . . .
H7A H 0.0976 0.6788 0.2703 0.131 Uiso 1 1 calc R U . . .
H7B H -0.0603 0.6185 0.3533 0.131 Uiso 1 1 calc R U . . .
H7C H -0.0332 0.5257 0.2692 0.131 Uiso 1 1 calc R U . . .
C8 C 0.3589(5) 0.5860(3) 0.40084(17) 0.0834(7) Uani 1 1 d . . . . .
H8A H 0.4920 0.5278 0.4196 0.125 Uiso 1 1 calc R U . . .
H8B H 0.2492 0.6041 0.4506 0.125 Uiso 1 1 calc R U . . .
H8C H 0.4048 0.6837 0.3724 0.125 Uiso 1 1 calc R U . . .
C9 C 0.1318(4) 0.1277(2) 0.16063(14) 0.0553(5) Uani 1 1 d . . . . .
C10 C 0.2951(3) -0.0046(2) 0.13695(12) 0.0477(4) Uani 1 1 d . . . . .
C11 C 0.2491(4) -0.0992(2) 0.07248(13) 0.0544(5) Uani 1 1 d . . . . .
H11 H 0.1154 -0.0792 0.0450 0.065 Uiso 1 1 calc R U . . .
C12 C 0.3977(4) -0.2212(2) 0.04887(13) 0.0573(5) Uani 1 1 d . . . . .
H12 H 0.3652 -0.2843 0.0061 0.069 Uiso 1 1 calc R U . . .
C13 C 0.5962(3) -0.2491(2) 0.08947(12) 0.0525(5) Uani 1 1 d . . . . .
C14 C 0.6473(4) -0.1579(2) 0.15322(13) 0.0557(5) Uani 1 1 d . . . . .
H14 H 0.7820 -0.1780 0.1800 0.067 Uiso 1 1 calc R U . . .
C15 C 0.4960(3) -0.0364(2) 0.17675(12) 0.0527(5) Uani 1 1 d . . . . .
H15 H 0.5288 0.0255 0.2200 0.063 Uiso 1 1 calc R U . . .
Cl1 Cl 0.78497(10) -0.40423(7) 0.06051(4) 0.0762(2) Uani 1 1 d . . . . .
O1 O -0.0378(3) 0.1603(2) 0.12214(13) 0.0801(5) Uani 1 1 d . . . . .
S1 S 0.00467(12) 0.01513(6) 0.34789(4) 0.0742(2) Uani 1 1 d . . . . .
S2 S 0.15319(11) 0.31534(6) 0.39823(3) 0.06426(19) Uani 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
C1 S1 1.790(3) . ?
C2 C3 1.329(3) . ?
C2 S2 1.755(2) . ?
C2 S1 1.7728(19) . ?
C3 C9 1.503(3) . ?
C3 C4 1.507(3) . ?
C4 C5 1.523(3) . ?
C5 C6 1.523(3) . ?
C6 C7 1.514(3) . ?
C6 C8 1.524(3) . ?
C6 S2 1.831(2) . ?
C9 O1 1.219(3) . ?
C9 C10 1.486(3) . ?
C10 C15 1.388(3) . ?
C10 C11 1.394(3) . ?
C11 C12 1.370(3) . ?
C12 C13 1.378(3) . ?
C13 C14 1.375(3) . ?
C13 Cl1 1.738(2) . ?
C14 C15 1.375(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
C3 C2 S2 125.77(16) . . ?
C3 C2 S1 119.41(16) . . ?
S2 C2 S1 114.50(11) . . ?
C2 C3 C9 121.38(18) . . ?
C2 C3 C4 124.85(19) . . ?
C9 C3 C4 113.77(17) . . ?
C3 C4 C5 114.05(18) . . ?
C6 C5 C4 113.54(19) . . ?
C7 C6 C5 111.8(2) . . ?
C7 C6 C8 109.9(2) . . ?
C5 C6 C8 110.19(19) . . ?
C7 C6 S2 110.19(16) . . ?
C5 C6 S2 108.15(14) . . ?
C8 C6 S2 106.52(16) . . ?
O1 C9 C10 121.43(19) . . ?
O1 C9 C3 119.87(19) . . ?
C10 C9 C3 118.54(17) . . ?
C15 C10 C11 118.46(18) . . ?
C15 C10 C9 121.71(17) . . ?
C11 C10 C9 119.83(17) . . ?
C12 C11 C10 121.02(18) . . ?
C11 C12 C13 119.01(18) . . ?
C14 C13 C12 121.51(18) . . ?
C14 C13 Cl1 119.10(16) . . ?
C12 C13 Cl1 119.38(15) . . ?
C13 C14 C15 118.93(19) . . ?
C14 C15 C10 121.07(18) . . ?
C2 S1 C1 104.01(12) . . ?
C2 S2 C6 101.39(9) . . ?

_refine_diff_density_max         0.329
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.041

