# Electronic Supplementary Material (ESI) for ChemComm.
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#                                CCDC 
# 
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# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
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#  fide research purposes only. It may contain copyright material
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data_dm13437

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H12 Cl N O S2'
_chemical_formula_weight         333.84

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      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                   7.4568(11)
_cell_length_b                   10.4808(16)
_cell_length_c                   10.804(3)
_cell_angle_alpha                110.442(3)
_cell_angle_beta                 98.772(4)
_cell_angle_gamma                103.159(2)
_cell_volume                     745.1(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    140(2)
_cell_measurement_reflns_used    3741
_cell_measurement_theta_min      2.18
_cell_measurement_theta_max      30.47

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.488
_exptl_crystal_F_000             344
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.533
_shelx_estimated_absorpt_T_min   0.924
_shelx_estimated_absorpt_T_max   0.959
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5764
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      140(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7423
_diffrn_reflns_av_unetI/netI     0.0401
_diffrn_reflns_av_R_equivalents  0.0231
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.080
_diffrn_reflns_theta_max         30.554
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             4501
_reflns_number_gt                3825
_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    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.0773P)²+0.3292P] 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         4501
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0480
_refine_ls_R_factor_gt           0.0399
_refine_ls_wR_factor_ref         0.1347
_refine_ls_wR_factor_gt          0.1230
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.071
_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
Cl1 Cl 0.51861(7) 0.28913(5) -0.28880(4) 0.02706(12) Uani 1 1 d . . . . .
N1 N 0.7067(2) 0.41024(15) 0.10724(14) 0.0200(3) Uani 1 1 d . . . . .
O1 O 0.79508(19) 0.59813(14) -0.10123(13) 0.0239(3) Uani 1 1 d . . . . .
S1 S 0.48117(6) 0.14592(4) -0.02345(4) 0.02272(12) Uani 1 1 d . . . . .
S2 S 1.03133(7) 0.86224(5) 0.09464(5) 0.02817(13) Uani 1 1 d . . . . .
C1 C 0.6009(2) 0.30937(17) -0.01974(16) 0.0178(3) Uani 1 1 d . . . . .
C2 C 0.6194(2) 0.36734(18) -0.11613(16) 0.0186(3) Uani 1 1 d . . . . .
C3 C 0.7432(2) 0.51110(18) -0.05048(17) 0.0185(3) Uani 1 1 d . . . . .
C4 C 0.7980(2) 0.53782(17) 0.09677(17) 0.0180(3) Uani 1 1 d . . . . .
C5 C 0.9044(2) 0.65775(18) 0.20687(18) 0.0204(3) Uani 1 1 d . . . . .
H5 H 0.9153 0.6464 0.2909 0.024 Uiso 1 1 calc R U . . .
C6 C 1.0041(2) 0.79892(18) 0.22110(19) 0.0213(3) Uani 1 1 d . . . . .
C7 C 1.0957(3) 0.91067(18) 0.3546(2) 0.0247(4) Uani 1 1 d . . . . .
H7 H 1.0987 0.8997 0.4384 0.030 Uiso 1 1 calc R U . . .
C8 C 1.1815(3) 1.0404(2) 0.3420(2) 0.0331(4) Uani 1 1 d . . . . .
H8 H 1.2486 1.1272 0.4185 0.040 Uiso 1 1 calc R U . . .
C9 C 1.1588(3) 1.0288(2) 0.2113(2) 0.0335(4) Uani 1 1 d . . . . .
H9 H 1.2091 1.1061 0.1873 0.040 Uiso 1 1 calc R U . . .
C10 C 0.3807(3) 0.0305(2) -0.20082(19) 0.0277(4) Uani 1 1 d . . . . .
H10A H 0.2817 0.0631 -0.2397 0.042 Uiso 1 1 calc R U . . .
H10B H 0.3249 -0.0674 -0.2096 0.042 Uiso 1 1 calc R U . . .
H10C H 0.4809 0.0327 -0.2499 0.042 Uiso 1 1 calc R U . . .
C11 C 0.7294(2) 0.38425(17) 0.22965(16) 0.0179(3) Uani 1 1 d . . . . .
C12 C 0.5849(2) 0.38626(18) 0.29780(18) 0.0208(3) Uani 1 1 d . . . . .
H12 H 0.4731 0.4056 0.2644 0.025 Uiso 1 1 calc R U . . .
C13 C 0.6074(3) 0.35941(18) 0.41560(17) 0.0219(3) Uani 1 1 d . . . . .
H13 H 0.5104 0.3605 0.4633 0.026 Uiso 1 1 calc R U . . .
C14 C 0.7710(3) 0.33104(18) 0.46388(17) 0.0224(3) Uani 1 1 d . . . . .
H14 H 0.7854 0.3127 0.5444 0.027 Uiso 1 1 calc R U . . .
C15 C 0.9142(3) 0.32937(19) 0.39481(18) 0.0226(3) Uani 1 1 d . . . . .
H15 H 1.0257 0.3095 0.4280 0.027 Uiso 1 1 calc R U . . .
C16 C 0.8942(2) 0.35666(19) 0.27744(17) 0.0207(3) Uani 1 1 d . . . . .
H16 H 0.9919 0.3565 0.2304 0.025 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
Cl1 C2 1.7148(17) . ?
N1 C1 1.378(2) . ?
N1 C4 1.407(2) . ?
N1 C11 1.434(2) . ?
O1 C3 1.239(2) . ?
S1 C1 1.7257(17) . ?
S1 C10 1.7965(19) . ?
S2 C9 1.697(2) . ?
S2 C6 1.7335(18) . ?
C1 C2 1.386(2) . ?
C2 C3 1.430(2) . ?
C3 C4 1.488(2) . ?
C4 C5 1.356(2) . ?
C5 C6 1.439(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.440(3) . ?
C7 C8 1.427(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.355(3) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C16 1.390(2) . ?
C11 C12 1.395(2) . ?
C12 C13 1.391(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.389(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.393(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.388(2) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?

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
C1 N1 C4 110.02(14) . . ?
C1 N1 C11 124.37(14) . . ?
C4 N1 C11 125.48(14) . . ?
C1 S1 C10 105.95(9) . . ?
C9 S2 C6 92.06(10) . . ?
N1 C1 C2 109.26(15) . . ?
N1 C1 S1 115.42(12) . . ?
C2 C1 S1 135.32(13) . . ?
C1 C2 C3 109.39(14) . . ?
C1 C2 Cl1 128.78(13) . . ?
C3 C2 Cl1 121.82(13) . . ?
O1 C3 C2 129.02(16) . . ?
O1 C3 C4 125.89(16) . . ?
C2 C3 C4 105.09(14) . . ?
C5 C4 N1 122.83(15) . . ?
C5 C4 C3 130.86(15) . . ?
N1 C4 C3 106.23(14) . . ?
C4 C5 C6 132.44(16) . . ?
C4 C5 H5 113.8 . . ?
C6 C5 H5 113.8 . . ?
C5 C6 C7 120.33(16) . . ?
C5 C6 S2 128.79(14) . . ?
C7 C6 S2 110.88(13) . . ?
C8 C7 C6 109.77(18) . . ?
C8 C7 H7 125.1 . . ?
C6 C7 H7 125.1 . . ?
C9 C8 C7 114.05(19) . . ?
C9 C8 H8 123.0 . . ?
C7 C8 H8 123.0 . . ?
C8 C9 S2 113.24(15) . . ?
C8 C9 H9 123.4 . . ?
S2 C9 H9 123.4 . . ?
S1 C10 H10A 109.5 . . ?
S1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
S1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C16 C11 C12 121.37(15) . . ?
C16 C11 N1 119.40(15) . . ?
C12 C11 N1 119.24(15) . . ?
C13 C12 C11 118.78(16) . . ?
C13 C12 H12 120.6 . . ?
C11 C12 H12 120.6 . . ?
C14 C13 C12 120.32(16) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C13 C14 C15 120.29(16) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C16 C15 C14 120.04(16) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C15 C16 C11 119.20(16) . . ?
C15 C16 H16 120.4 . . ?
C11 C16 H16 120.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 N1 C1 C2 -0.1(2) . . . . ?
C11 N1 C1 C2 -176.18(15) . . . . ?
C4 N1 C1 S1 179.62(11) . . . . ?
C11 N1 C1 S1 3.5(2) . . . . ?
C10 S1 C1 N1 -173.20(13) . . . . ?
C10 S1 C1 C2 6.4(2) . . . . ?
N1 C1 C2 C3 0.54(19) . . . . ?
S1 C1 C2 C3 -179.04(14) . . . . ?
N1 C1 C2 Cl1 -179.96(13) . . . . ?
S1 C1 C2 Cl1 0.5(3) . . . . ?
C1 C2 C3 O1 179.96(17) . . . . ?
Cl1 C2 C3 O1 0.4(3) . . . . ?
C1 C2 C3 C4 -0.78(18) . . . . ?
Cl1 C2 C3 C4 179.68(12) . . . . ?
C1 N1 C4 C5 176.72(16) . . . . ?
C11 N1 C4 C5 -7.2(3) . . . . ?
C1 N1 C4 C3 -0.43(18) . . . . ?
C11 N1 C4 C3 175.65(15) . . . . ?
O1 C3 C4 C5 3.2(3) . . . . ?
C2 C3 C4 C5 -176.10(18) . . . . ?
O1 C3 C4 N1 -179.98(16) . . . . ?
C2 C3 C4 N1 0.73(17) . . . . ?
N1 C4 C5 C6 -177.78(17) . . . . ?
C3 C4 C5 C6 -1.4(3) . . . . ?
C4 C5 C6 C7 175.25(18) . . . . ?
C4 C5 C6 S2 -3.7(3) . . . . ?
C9 S2 C6 C5 179.21(17) . . . . ?
C9 S2 C6 C7 0.21(14) . . . . ?
C5 C6 C7 C8 -179.04(16) . . . . ?
S2 C6 C7 C8 0.1(2) . . . . ?
C6 C7 C8 C9 -0.4(3) . . . . ?
C7 C8 C9 S2 0.6(3) . . . . ?
C6 S2 C9 C8 -0.45(18) . . . . ?
C1 N1 C11 C16 99.5(2) . . . . ?
C4 N1 C11 C16 -76.1(2) . . . . ?
C1 N1 C11 C12 -80.1(2) . . . . ?
C4 N1 C11 C12 104.4(2) . . . . ?
C16 C11 C12 C13 -0.2(3) . . . . ?
N1 C11 C12 C13 179.32(15) . . . . ?
C11 C12 C13 C14 -0.1(3) . . . . ?
C12 C13 C14 C15 0.1(3) . . . . ?
C13 C14 C15 C16 0.3(3) . . . . ?
C14 C15 C16 C11 -0.6(3) . . . . ?
C12 C11 C16 C15 0.6(3) . . . . ?
N1 C11 C16 C15 -179.01(15) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C12 H12 O1 0.95 2.44 3.344(2) 159.2 2_665
C16 H16 O1 0.95 2.34 3.270(2) 164.9 2_765

_refine_diff_density_max         0.626
_refine_diff_density_min         -0.566
_refine_diff_density_rms         0.094

_shelxl_version_number           2013-4

_database_code_depnum_ccdc_archive 'CCDC 999801'
