# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  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.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
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# 
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#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_cd1221a

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H14 Cl N O S'
_chemical_formula_sum            'C13 H14 Cl N O S'
_chemical_formula_weight         267.76

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
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'
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'
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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P2(1)/c
_symmetry_space_group_name_Hall  '-P 2ybc'

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

_cell_length_a                   9.1435(17)
_cell_length_b                   6.0132(11)
_cell_length_c                   23.209(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.530(3)
_cell_angle_gamma                90.00
_cell_volume                     1276.0(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    98(2)
_cell_measurement_reflns_used    6668
_cell_measurement_theta_min      2.2
_cell_measurement_theta_max      40.2

_exptl_crystal_description       platelet
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.394
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             560
_exptl_absorpt_coefficient_mu    0.445
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.719
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'ABSCOR (Higashi, 1995)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      98(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  
;
Saturn724 (2x2 bin mode)
;
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 28.5714
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        <1
_diffrn_reflns_number            7393
_diffrn_reflns_av_R_equivalents  0.0407
_diffrn_reflns_av_sigmaI/netI    0.0396
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         2.23
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_reduction_process 'Lp corrections applied'
_reflns_number_total             2513
_reflns_number_gt                2348
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r5 (Rigaku, 2010)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r5 (Rigaku, 2010)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r5 (Rigaku, 2010)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.0632P)²+0.6000P] 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         2513
_refine_ls_number_parameters     196
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0397
_refine_ls_R_factor_gt           0.0372
_refine_ls_wR_factor_ref         0.1019
_refine_ls_wR_factor_gt          0.0993
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_restrained_S_all      1.003
_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 -0.37582(5) -0.28153(7) 0.00745(2) 0.03125(16) Uani 1 1 d . . .
S1 S -0.00177(4) 0.67920(7) 0.109234(17) 0.02229(15) Uani 1 1 d . . .
O1 O -0.50343(14) 0.1590(3) 0.19098(6) 0.0341(3) Uani 1 1 d . . .
N1 N -0.39553(15) 0.2771(3) 0.17175(6) 0.0237(3) Uani 1 1 d . . .
C1 C -0.31124(18) -0.0477(3) 0.04368(7) 0.0224(3) Uani 1 1 d . . .
C2 C -0.19283(19) 0.0708(3) 0.02042(7) 0.0231(4) Uani 1 1 d . . .
C3 C -0.14001(18) 0.2538(3) 0.04877(7) 0.0209(3) Uani 1 1 d . . .
C4 C -0.20391(17) 0.3291(3) 0.10063(7) 0.0181(3) Uani 1 1 d . . .
C5 C -0.15488(18) 0.5217(3) 0.13168(7) 0.0199(3) Uani 1 1 d . . .
C6 C -0.23356(19) 0.5862(3) 0.17886(7) 0.0236(4) Uani 1 1 d . . .
C7 C -0.35341(19) 0.4637(3) 0.19834(7) 0.0260(4) Uani 1 1 d . . .
C8 C -0.32418(18) 0.2072(3) 0.12176(7) 0.0198(3) Uani 1 1 d . . .
C9 C -0.37738(18) 0.0163(3) 0.09347(7) 0.0225(4) Uani 1 1 d . . .
C10 C 0.15210(19) 0.5535(3) 0.15106(7) 0.0228(4) Uani 1 1 d . . .
C11 C 0.1584(2) 0.3020(3) 0.14257(9) 0.0296(4) Uani 1 1 d . . .
C12 C 0.2868(2) 0.6664(3) 0.12601(9) 0.0304(4) Uani 1 1 d . . .
C13 C 0.1382(2) 0.6101(4) 0.21471(8) 0.0313(4) Uani 1 1 d . . .
H7A H -0.406(3) 0.500(4) 0.2297(10) 0.038 Uiso 1 1 d . . .
H6A H -0.206(3) 0.718(4) 0.1999(10) 0.038 Uiso 1 1 d . . .
H3A H -0.063(3) 0.333(4) 0.0341(10) 0.038 Uiso 1 1 d . . .
H2A H -0.148(3) 0.027(4) -0.0147(10) 0.038 Uiso 1 1 d . . .
H9A H -0.460(3) -0.060(4) 0.1098(10) 0.038 Uiso 1 1 d . . .
H11A H 0.244(3) 0.240(4) 0.1626(12) 0.047 Uiso 1 1 d . . .
H11B H 0.176(3) 0.263(4) 0.1015(12) 0.047 Uiso 1 1 d . . .
H11C H 0.071(3) 0.232(4) 0.1611(11) 0.047 Uiso 1 1 d . . .
H13A H 0.050(3) 0.548(4) 0.2311(11) 0.047 Uiso 1 1 d . . .
H13B H 0.226(3) 0.547(4) 0.2349(11) 0.047 Uiso 1 1 d . . .
H13C H 0.129(3) 0.768(4) 0.2206(11) 0.047 Uiso 1 1 d . . .
H12A H 0.282(3) 0.832(5) 0.1301(11) 0.047 Uiso 1 1 d . . .
H12B H 0.369(3) 0.616(4) 0.1462(11) 0.047 Uiso 1 1 d . . .
H12C H 0.300(3) 0.634(4) 0.0855(12) 0.047 Uiso 1 1 d . . .

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 0.0336(3) 0.0237(3) 0.0363(3) -0.00393(17) -0.01011(19) -0.00294(17)
S1 0.0230(2) 0.0193(2) 0.0245(2) 0.00412(14) -0.00148(16) -0.00275(15)
O1 0.0239(7) 0.0510(9) 0.0276(7) 0.0073(6) 0.0076(5) -0.0092(6)
N1 0.0170(7) 0.0354(8) 0.0186(7) 0.0063(6) 0.0005(5) 0.0011(6)
C1 0.0223(8) 0.0205(8) 0.0241(8) 0.0025(6) -0.0079(6) 0.0009(6)
C2 0.0231(8) 0.0254(9) 0.0208(8) 0.0006(6) 0.0000(6) 0.0033(7)
C3 0.0190(8) 0.0235(8) 0.0203(8) 0.0033(6) 0.0017(6) -0.0008(6)
C4 0.0167(8) 0.0195(8) 0.0180(7) 0.0041(6) -0.0017(6) 0.0022(6)
C5 0.0190(8) 0.0199(8) 0.0208(8) 0.0035(6) -0.0024(6) 0.0010(6)
C6 0.0240(8) 0.0252(9) 0.0216(8) -0.0005(7) -0.0037(6) 0.0040(7)
C7 0.0225(8) 0.0384(10) 0.0173(8) -0.0001(7) 0.0021(6) 0.0069(7)
C8 0.0178(8) 0.0246(8) 0.0170(7) 0.0056(6) -0.0004(6) 0.0025(6)
C9 0.0173(8) 0.0261(9) 0.0240(8) 0.0076(7) -0.0030(6) -0.0017(6)
C10 0.0221(8) 0.0195(8) 0.0267(8) 0.0009(6) -0.0037(6) -0.0015(6)
C11 0.0284(10) 0.0195(9) 0.0407(11) 0.0000(7) -0.0083(8) 0.0002(7)
C12 0.0229(9) 0.0267(10) 0.0415(11) 0.0022(8) -0.0014(8) -0.0038(7)
C13 0.0317(10) 0.0361(11) 0.0260(9) -0.0019(8) -0.0064(7) -0.0030(8)

_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 C1 1.7390(17) . ?
S1 C5 1.7724(17) . ?
S1 C10 1.8622(17) . ?
O1 N1 1.298(2) . ?
N1 C7 1.336(2) . ?
N1 C8 1.401(2) . ?
C1 C9 1.365(2) . ?
C1 C2 1.408(2) . ?
C2 C3 1.368(2) . ?
C2 H2A 0.95(2) . ?
C3 C4 1.417(2) . ?
C3 H3A 0.92(2) . ?
C4 C8 1.413(2) . ?
C4 C5 1.434(2) . ?
C5 C6 1.372(2) . ?
C6 C7 1.399(3) . ?
C6 H6A 0.96(2) . ?
C7 H7A 0.90(2) . ?
C8 C9 1.407(2) . ?
C9 H9A 0.96(2) . ?
C10 C13 1.522(2) . ?
C10 C12 1.526(2) . ?
C10 C11 1.527(2) . ?
C11 H11A 0.98(3) . ?
C11 H11B 1.00(3) . ?
C11 H11C 1.00(3) . ?
C12 H12A 1.00(3) . ?
C12 H12B 0.93(3) . ?
C12 H12C 0.97(3) . ?
C13 H13A 0.97(3) . ?
C13 H13B 1.00(3) . ?
C13 H13C 0.96(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
C5 S1 C10 103.00(8) . . ?
O1 N1 C7 121.17(15) . . ?
O1 N1 C8 118.81(15) . . ?
C7 N1 C8 120.02(15) . . ?
C9 C1 C2 122.05(16) . . ?
C9 C1 Cl1 119.09(13) . . ?
C2 C1 Cl1 118.86(13) . . ?
C3 C2 C1 119.47(16) . . ?
C3 C2 H2A 119.0(14) . . ?
C1 C2 H2A 121.6(14) . . ?
C2 C3 C4 121.28(15) . . ?
C2 C3 H3A 120.6(15) . . ?
C4 C3 H3A 118.1(15) . . ?
C8 C4 C3 117.20(15) . . ?
C8 C4 C5 119.04(15) . . ?
C3 C4 C5 123.75(15) . . ?
C6 C5 C4 117.75(15) . . ?
C6 C5 S1 120.34(13) . . ?
C4 C5 S1 121.87(12) . . ?
C5 C6 C7 121.83(16) . . ?
C5 C6 H6A 120.2(14) . . ?
C7 C6 H6A 118.0(14) . . ?
N1 C7 C6 121.09(16) . . ?
N1 C7 H7A 114.9(15) . . ?
C6 C7 H7A 124.0(15) . . ?
N1 C8 C9 118.01(15) . . ?
N1 C8 C4 120.11(15) . . ?
C9 C8 C4 121.88(15) . . ?
C1 C9 C8 118.11(15) . . ?
C1 C9 H9A 123.7(14) . . ?
C8 C9 H9A 118.2(14) . . ?
C13 C10 C12 110.19(15) . . ?
C13 C10 C11 110.50(16) . . ?
C12 C10 C11 111.11(16) . . ?
C13 C10 S1 110.24(13) . . ?
C12 C10 S1 103.26(12) . . ?
C11 C10 S1 111.35(12) . . ?
C10 C11 H11A 110.4(15) . . ?
C10 C11 H11B 111.3(15) . . ?
H11A C11 H11B 103(2) . . ?
C10 C11 H11C 109.3(15) . . ?
H11A C11 H11C 106(2) . . ?
H11B C11 H11C 117(2) . . ?
C10 C12 H12A 111.8(14) . . ?
C10 C12 H12B 108.2(15) . . ?
H12A C12 H12B 108(2) . . ?
C10 C12 H12C 112.9(15) . . ?
H12A C12 H12C 107(2) . . ?
H12B C12 H12C 108(2) . . ?
C10 C13 H13A 111.9(15) . . ?
C10 C13 H13B 107.1(14) . . ?
H13A C13 H13B 110(2) . . ?
C10 C13 H13C 111.5(16) . . ?
H13A C13 H13C 105(2) . . ?
H13B C13 H13C 112(2) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.492
_refine_diff_density_min         -0.284
_refine_diff_density_rms         0.061
_database_code_depnum_ccdc_archive 'CCDC 1005394'
