# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_cr767m
_audit_block_doi                 10.5517/cc1k4gx2
_database_code_depnum_ccdc_archive 'CCDC 1434274'
_audit_update_record             
;
2016-01-12 deposited with the CCDC.
2016-01-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H13 Cl N2 S'
_chemical_formula_weight         288.78

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'
Cl Cl 0.1484 0.1585 '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                   8.8629(10)
_cell_length_b                   9.1256(10)
_cell_length_c                   10.0677(11)
_cell_angle_alpha                64.158(2)
_cell_angle_beta                 68.430(2)
_cell_angle_gamma                81.687(2)
_cell_volume                     681.40(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2324
_cell_measurement_theta_min      2.85
_cell_measurement_theta_max      23.54

_exptl_crystal_description       BLOCKS
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             300
_exptl_absorpt_coefficient_mu    0.420
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.8739
_exptl_absorpt_correction_T_max  0.9514
_exptl_absorpt_process_details   'BRUKER SADABS'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(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 SMART APEX CCD DIFFRACTOMETER'
_diffrn_measurement_method       'OMEGA-PHI SCAN'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5276
_diffrn_reflns_av_R_equivalents  0.0189
_diffrn_reflns_av_sigmaI/netI    0.0272
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.39
_diffrn_reflns_theta_max         25.99
_reflns_number_total             2649
_reflns_number_gt                2553
_reflns_threshold_expression     >2sigma(I)

_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-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ORTEP
_computing_publication_material  ?

_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)+(0.0471P)²+0.2963P] 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         2649
_refine_ls_number_parameters     174
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0352
_refine_ls_R_factor_gt           0.0341
_refine_ls_wR_factor_ref         0.0926
_refine_ls_wR_factor_gt          0.0917
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_restrained_S_all      1.084
_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
Cl1 Cl 1.06368(5) 0.91675(5) 0.32578(5) 0.03553(14) Uani 1 1 d . . .
S1 S 0.47964(5) 0.24980(5) 0.86898(5) 0.03043(14) Uani 1 1 d . . .
N1 N 0.28011(16) 0.67189(15) 0.66950(15) 0.0256(3) Uani 1 1 d . . .
N2 N 0.20246(16) 0.41137(15) 0.82990(14) 0.0237(3) Uani 1 1 d . . .
C1 C 0.59566(19) 0.81578(19) 0.58511(19) 0.0269(3) Uani 1 1 d . . .
H1 H 0.5070 0.8680 0.6297 0.032 Uiso 1 1 calc R . .
C2 C 0.7443(2) 0.89686(19) 0.49924(19) 0.0277(3) Uani 1 1 d . . .
H2 H 0.7562 1.0025 0.4860 0.033 Uiso 1 1 calc R . .
C3 C 0.87473(18) 0.81742(19) 0.43368(17) 0.0250(3) Uani 1 1 d . . .
C4 C 0.86026(19) 0.66006(19) 0.45118(18) 0.0264(3) Uani 1 1 d . . .
H4 H 0.9493 0.6091 0.4054 0.032 Uiso 1 1 calc R . .
C5 C 0.71082(19) 0.58017(18) 0.53815(18) 0.0258(3) Uani 1 1 d . . .
H5 H 0.7000 0.4743 0.5514 0.031 Uiso 1 1 calc R . .
C6 C 0.57638(19) 0.65647(18) 0.60612(17) 0.0239(3) Uani 1 1 d . . .
C7 C 0.41341(19) 0.57948(18) 0.68897(17) 0.0241(3) Uani 1 1 d . . .
C8 C 0.15360(19) 0.56806(18) 0.75493(18) 0.0247(3) Uani 1 1 d . . .
C9 C -0.0133(2) 0.5941(2) 0.77826(19) 0.0286(3) Uani 1 1 d . . .
H9 H -0.0503 0.6979 0.7303 0.034 Uiso 1 1 calc R . .
C10 C -0.1198(2) 0.4652(2) 0.87201(19) 0.0302(4) Uani 1 1 d . . .
H10 H -0.2297 0.4821 0.8869 0.036 Uiso 1 1 calc R . .
C11 C -0.0661(2) 0.3053(2) 0.94766(18) 0.0284(3) Uani 1 1 d . . .
C12 C 0.0943(2) 0.28168(19) 0.92515(17) 0.0261(3) Uani 1 1 d . . .
H12 H 0.1314 0.1782 0.9738 0.031 Uiso 1 1 calc R . .
C13 C 0.37009(19) 0.41761(18) 0.78744(17) 0.0245(3) Uani 1 1 d . . .
C14 C 0.5062(2) 0.13871(19) 0.7501(2) 0.0328(4) Uani 1 1 d . . .
H14A H 0.4034 0.1268 0.7438 0.049 Uiso 1 1 calc R . .
H14B H 0.5483 0.0330 0.7971 0.049 Uiso 1 1 calc R . .
H14C H 0.5808 0.1976 0.6464 0.049 Uiso 1 1 calc R . .
C15 C -0.1853(2) 0.1652(2) 1.0513(2) 0.0346(4) Uani 1 1 d . . .
H15A H -0.1295 0.0689 1.0976 0.052 Uiso 1 1 calc R . .
H15B H -0.2358 0.1476 0.9898 0.052 Uiso 1 1 calc R . .
H15C H -0.2667 0.1898 1.1328 0.052 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl1 0.0242(2) 0.0397(2) 0.0380(2) -0.01390(19) -0.00560(17) -0.00717(16)
S1 0.0324(2) 0.0271(2) 0.0290(2) -0.00474(17) -0.01536(17) -0.00102(16)
N1 0.0266(7) 0.0228(6) 0.0267(7) -0.0114(5) -0.0067(5) -0.0010(5)
N2 0.0265(7) 0.0235(6) 0.0210(6) -0.0090(5) -0.0072(5) -0.0025(5)
C1 0.0257(8) 0.0249(8) 0.0303(8) -0.0134(6) -0.0073(6) 0.0010(6)
C2 0.0302(8) 0.0234(8) 0.0306(8) -0.0114(6) -0.0102(7) -0.0027(6)
C3 0.0228(8) 0.0283(8) 0.0220(7) -0.0077(6) -0.0079(6) -0.0029(6)
C4 0.0266(8) 0.0277(8) 0.0241(7) -0.0105(6) -0.0093(6) 0.0037(6)
C5 0.0317(8) 0.0207(7) 0.0249(7) -0.0090(6) -0.0101(6) 0.0000(6)
C6 0.0274(8) 0.0223(7) 0.0211(7) -0.0073(6) -0.0088(6) -0.0019(6)
C7 0.0266(8) 0.0242(7) 0.0235(7) -0.0117(6) -0.0082(6) -0.0004(6)
C8 0.0297(8) 0.0228(7) 0.0223(7) -0.0109(6) -0.0074(6) -0.0008(6)
C9 0.0295(8) 0.0299(8) 0.0289(8) -0.0154(7) -0.0097(7) 0.0026(6)
C10 0.0253(8) 0.0390(9) 0.0297(8) -0.0189(7) -0.0067(6) -0.0010(7)
C11 0.0311(8) 0.0338(8) 0.0213(7) -0.0128(6) -0.0052(6) -0.0078(7)
C12 0.0320(8) 0.0247(8) 0.0206(7) -0.0077(6) -0.0076(6) -0.0059(6)
C13 0.0266(8) 0.0240(7) 0.0234(7) -0.0086(6) -0.0095(6) -0.0022(6)
C14 0.0327(9) 0.0233(8) 0.0348(9) -0.0069(7) -0.0093(7) -0.0009(6)
C15 0.0314(9) 0.0389(9) 0.0306(9) -0.0141(7) -0.0039(7) -0.0105(7)

_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 1.7462(15) . ?
S1 C13 1.7384(16) . ?
S1 C14 1.8161(18) . ?
N1 C8 1.335(2) . ?
N1 C7 1.372(2) . ?
N2 C12 1.3790(19) . ?
N2 C8 1.3864(19) . ?
N2 C13 1.389(2) . ?
C1 C2 1.385(2) . ?
C1 C6 1.402(2) . ?
C1 H1 0.9300 . ?
C2 C3 1.382(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.388(2) . ?
C4 C5 1.387(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.396(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.474(2) . ?
C7 C13 1.386(2) . ?
C8 C9 1.411(2) . ?
C9 C10 1.365(2) . ?
C9 H9 0.9300 . ?
C10 C11 1.426(2) . ?
C10 H10 0.9300 . ?
C11 C12 1.356(2) . ?
C11 C15 1.502(2) . ?
C12 H12 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 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
C13 S1 C14 102.50(8) . . ?
C8 N1 C7 105.40(13) . . ?
C12 N2 C8 122.41(13) . . ?
C12 N2 C13 130.52(13) . . ?
C8 N2 C13 107.06(12) . . ?
C2 C1 C6 121.22(15) . . ?
C2 C1 H1 119.4 . . ?
C6 C1 H1 119.4 . . ?
C3 C2 C1 118.58(14) . . ?
C3 C2 H2 120.7 . . ?
C1 C2 H2 120.7 . . ?
C2 C3 C4 121.89(14) . . ?
C2 C3 Cl1 119.42(12) . . ?
C4 C3 Cl1 118.68(12) . . ?
C5 C4 C3 118.85(14) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
C4 C5 C6 120.88(14) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C5 C6 C1 118.57(14) . . ?
C5 C6 C7 122.09(13) . . ?
C1 C6 C7 119.19(14) . . ?
N1 C7 C13 111.38(14) . . ?
N1 C7 C6 119.72(13) . . ?
C13 C7 C6 128.88(14) . . ?
N1 C8 N2 111.18(14) . . ?
N1 C8 C9 130.64(14) . . ?
N2 C8 C9 118.18(14) . . ?
C10 C9 C8 119.21(15) . . ?
C10 C9 H9 120.4 . . ?
C8 C9 H9 120.4 . . ?
C9 C10 C11 121.43(15) . . ?
C9 C10 H10 119.3 . . ?
C11 C10 H10 119.3 . . ?
C12 C11 C10 118.91(15) . . ?
C12 C11 C15 120.43(16) . . ?
C10 C11 C15 120.66(15) . . ?
C11 C12 N2 119.86(15) . . ?
C11 C12 H12 120.1 . . ?
N2 C12 H12 120.1 . . ?
C7 C13 N2 104.97(13) . . ?
C7 C13 S1 132.54(12) . . ?
N2 C13 S1 122.15(11) . . ?
S1 C14 H14A 109.5 . . ?
S1 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
S1 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C11 C15 H15A 109.5 . . ?
C11 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C11 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        25.99
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.290
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.079
