# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_svwfp16_5
_database_code_depnum_ccdc_archive 'CCDC 1037548'
_audit_update_record             
;
2014-12-04 deposited with the CCDC.
2015-01-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          '388390 C '
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H15 Cl N2 O S'
_chemical_formula_weight         270.77

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           triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.1948(3)
_cell_length_b                   10.9643(5)
_cell_length_c                   11.2530(5)
_cell_angle_alpha                110.753(2)
_cell_angle_beta                 98.248(2)
_cell_angle_gamma                103.002(3)
_cell_volume                     675.19(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    3302
_cell_measurement_theta_min      3.41
_cell_measurement_theta_max      26.61

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             284
_exptl_absorpt_coefficient_mu    0.423
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9354
_exptl_absorpt_correction_T_max  0.9916
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6165
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0575
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.00
_diffrn_reflns_theta_max         27.10
_reflns_number_total             6165
_reflns_number_gt                4708
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker AXS SAINT V7.60A'
_computing_data_reduction        'Bruker AXS SAINT V7.60A'
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_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)+(0.0500P)²+0.5500P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6165
_refine_ls_number_parameters     161
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0781
_refine_ls_R_factor_gt           0.0508
_refine_ls_wR_factor_ref         0.1253
_refine_ls_wR_factor_gt          0.1131
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_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 -0.28688(13) 0.53165(7) 0.75988(7) 0.0447(2) Uani 1 1 d . . .
S1 S 0.04250(11) -0.00223(7) 0.66042(6) 0.02556(15) Uani 1 1 d . . .
O1 O 0.3926(3) -0.14048(17) 0.78167(16) 0.0272(4) Uani 1 1 d . . .
N1 N 0.0481(3) -0.1055(2) 0.83385(19) 0.0233(4) Uani 1 1 d . . .
H1 H 0.038(4) -0.116(3) 0.898(3) 0.028 Uiso 1 1 d . . .
N2 N -0.0397(3) 0.1001(2) 0.90181(18) 0.0234(4) Uani 1 1 d . . .
C1 C 0.0710(4) -0.1764(3) 0.6103(2) 0.0297(6) Uani 1 1 d . . .
C2 C 0.1524(4) -0.1865(2) 0.7421(2) 0.0222(5) Uani 1 1 d . . .
H2 H 0.0975 -0.2839 0.7310 0.027 Uiso 1 1 calc R . .
C3 C 0.0132(3) 0.0055(2) 0.8162(2) 0.0205(5) Uani 1 1 d . . .
C4 C 0.2398(5) -0.1927(3) 0.5254(2) 0.0446(8) Uani 1 1 d . . .
H4A H 0.1810 -0.1832 0.4445 0.067 Uiso 1 1 calc R . .
H4B H 0.2614 -0.2832 0.5036 0.067 Uiso 1 1 calc R . .
H4C H 0.3864 -0.1222 0.5730 0.067 Uiso 1 1 calc R . .
C5 C -0.1640(5) -0.2796(3) 0.5396(3) 0.0452(7) Uani 1 1 d . . .
H5A H -0.2659 -0.2685 0.5991 0.068 Uiso 1 1 calc R . .
H5B H -0.1502 -0.3724 0.5112 0.068 Uiso 1 1 calc R . .
H5C H -0.2271 -0.2643 0.4629 0.068 Uiso 1 1 calc R . .
C6 C 0.4763(4) -0.1737(3) 0.8872(2) 0.0317(6) Uani 1 1 d . . .
H6A H 0.4241 -0.2729 0.8602 0.048 Uiso 1 1 calc R . .
H6B H 0.4186 -0.1293 0.9628 0.048 Uiso 1 1 calc R . .
H6C H 0.6437 -0.1416 0.9112 0.048 Uiso 1 1 calc R . .
C7 C -0.0954(4) 0.2031(2) 0.8649(2) 0.0214(5) Uani 1 1 d . . .
C8 C -0.3218(4) 0.1887(2) 0.8144(2) 0.0253(5) Uani 1 1 d . . .
H8 H -0.4379 0.1090 0.8019 0.030 Uiso 1 1 calc R . .
C9 C -0.3798(4) 0.2898(2) 0.7820(2) 0.0256(5) Uani 1 1 d . . .
H9 H -0.5350 0.2796 0.7474 0.031 Uiso 1 1 calc R . .
C10 C -0.2116(4) 0.4047(2) 0.8001(2) 0.0280(6) Uani 1 1 d . . .
C11 C 0.0156(5) 0.4213(3) 0.8495(3) 0.0338(6) Uani 1 1 d . . .
H11 H 0.1311 0.5008 0.8608 0.041 Uiso 1 1 calc R . .
C12 C 0.0723(4) 0.3197(3) 0.8824(2) 0.0283(5) Uani 1 1 d . . .
H12 H 0.2277 0.3303 0.9171 0.034 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 0.0576(5) 0.0328(4) 0.0523(5) 0.0245(3) 0.0078(4) 0.0210(3)
S1 0.0358(3) 0.0352(3) 0.0178(3) 0.0161(3) 0.0114(3) 0.0212(3)
O1 0.0246(9) 0.0404(10) 0.0263(9) 0.0205(8) 0.0088(7) 0.0145(8)
N1 0.0308(11) 0.0340(11) 0.0194(10) 0.0186(9) 0.0120(9) 0.0197(9)
N2 0.0300(11) 0.0326(11) 0.0176(10) 0.0157(9) 0.0096(9) 0.0166(9)
C1 0.0413(15) 0.0356(14) 0.0187(12) 0.0106(11) 0.0071(11) 0.0245(12)
C2 0.0255(12) 0.0282(13) 0.0187(11) 0.0116(10) 0.0075(10) 0.0141(10)
C3 0.0157(11) 0.0302(12) 0.0226(11) 0.0170(10) 0.0031(9) 0.0104(10)
C4 0.078(2) 0.0592(19) 0.0233(14) 0.0237(13) 0.0263(15) 0.0501(17)
C5 0.0580(19) 0.0394(16) 0.0283(15) 0.0091(12) -0.0114(14) 0.0170(14)
C6 0.0313(14) 0.0441(15) 0.0312(14) 0.0229(12) 0.0082(11) 0.0197(12)
C7 0.0290(13) 0.0282(13) 0.0142(11) 0.0110(10) 0.0078(10) 0.0162(11)
C8 0.0281(13) 0.0316(13) 0.0217(12) 0.0158(11) 0.0081(10) 0.0093(11)
C9 0.0259(13) 0.0388(15) 0.0205(12) 0.0163(11) 0.0070(10) 0.0176(11)
C10 0.0422(15) 0.0264(13) 0.0210(12) 0.0108(10) 0.0072(11) 0.0186(12)
C11 0.0365(15) 0.0282(14) 0.0357(15) 0.0142(12) 0.0056(12) 0.0076(12)
C12 0.0254(13) 0.0347(14) 0.0268(13) 0.0130(11) 0.0051(11) 0.0126(11)

_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 C10 1.743(2) . ?
S1 C3 1.763(2) . ?
S1 C1 1.847(2) . ?
O1 C2 1.407(3) . ?
O1 C6 1.423(3) . ?
N1 C3 1.358(3) . ?
N1 C2 1.439(3) . ?
N1 H1 0.78(2) . ?
N2 C3 1.284(3) . ?
N2 C7 1.426(3) . ?
C1 C4 1.512(3) . ?
C1 C5 1.524(4) . ?
C1 C2 1.548(3) . ?
C2 H2 1.0000 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C12 1.385(3) . ?
C7 C8 1.387(3) . ?
C8 C9 1.385(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.371(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.383(4) . ?
C11 C12 1.389(3) . ?
C11 H11 0.9500 . ?
C12 H12 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
C3 S1 C1 92.12(10) . . ?
C2 O1 C6 111.60(17) . . ?
C3 N1 C2 116.35(18) . . ?
C3 N1 H1 121.3(19) . . ?
C2 N1 H1 121.0(19) . . ?
C3 N2 C7 117.47(17) . . ?
C4 C1 C5 112.1(2) . . ?
C4 C1 C2 113.17(19) . . ?
C5 C1 C2 108.9(2) . . ?
C4 C1 S1 109.85(18) . . ?
C5 C1 S1 108.86(17) . . ?
C2 C1 S1 103.55(15) . . ?
O1 C2 N1 112.69(19) . . ?
O1 C2 C1 109.78(18) . . ?
N1 C2 C1 106.32(17) . . ?
O1 C2 H2 109.3 . . ?
N1 C2 H2 109.3 . . ?
C1 C2 H2 109.3 . . ?
N2 C3 N1 123.46(19) . . ?
N2 C3 S1 125.64(16) . . ?
N1 C3 S1 110.87(16) . . ?
C1 C4 H4A 109.5 . . ?
C1 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C1 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C1 C5 H5A 109.5 . . ?
C1 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C1 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
O1 C6 H6A 109.5 . . ?
O1 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
O1 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C12 C7 C8 119.2(2) . . ?
C12 C7 N2 121.1(2) . . ?
C8 C7 N2 119.7(2) . . ?
C9 C8 C7 120.4(2) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C10 C9 C8 119.6(2) . . ?
C10 C9 H9 120.2 . . ?
C8 C9 H9 120.2 . . ?
C9 C10 C11 121.2(2) . . ?
C9 C10 Cl1 119.17(19) . . ?
C11 C10 Cl1 119.7(2) . . ?
C10 C11 C12 118.9(2) . . ?
C10 C11 H11 120.6 . . ?
C12 C11 H11 120.6 . . ?
C7 C12 C11 120.7(2) . . ?
C7 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?

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
C3 S1 C1 C4 -143.77(18) . . . . ?
C3 S1 C1 C5 93.18(18) . . . . ?
C3 S1 C1 C2 -22.61(17) . . . . ?
C6 O1 C2 N1 73.7(2) . . . . ?
C6 O1 C2 C1 -168.03(19) . . . . ?
C3 N1 C2 O1 88.2(2) . . . . ?
C3 N1 C2 C1 -32.1(3) . . . . ?
C4 C1 C2 O1 29.6(3) . . . . ?
C5 C1 C2 O1 154.9(2) . . . . ?
S1 C1 C2 O1 -89.32(18) . . . . ?
C4 C1 C2 N1 151.7(2) . . . . ?
C5 C1 C2 N1 -82.9(2) . . . . ?
S1 C1 C2 N1 32.8(2) . . . . ?
C7 N2 C3 N1 -173.4(2) . . . . ?
C7 N2 C3 S1 4.7(3) . . . . ?
C2 N1 C3 N2 -167.3(2) . . . . ?
C2 N1 C3 S1 14.4(3) . . . . ?
C1 S1 C3 N2 -171.8(2) . . . . ?
C1 S1 C3 N1 6.47(18) . . . . ?
C3 N2 C7 C12 -88.3(3) . . . . ?
C3 N2 C7 C8 93.7(3) . . . . ?
C12 C7 C8 C9 -0.1(3) . . . . ?
N2 C7 C8 C9 177.91(19) . . . . ?
C7 C8 C9 C10 0.0(3) . . . . ?
C8 C9 C10 C11 0.4(3) . . . . ?
C8 C9 C10 Cl1 -179.61(17) . . . . ?
C9 C10 C11 C12 -0.7(4) . . . . ?
Cl1 C10 C11 C12 179.32(18) . . . . ?
C8 C7 C12 C11 -0.2(3) . . . . ?
N2 C7 C12 C11 -178.2(2) . . . . ?
C10 C11 C12 C7 0.6(4) . . . . ?

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
N1 H1 N2 0.78(2) 2.20(3) 2.963(3) 169(3) 2_557

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        27.10
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.399
_refine_diff_density_min         -0.305
_refine_diff_density_rms         0.071
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: CH2Cl2/n-hexane'
