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# This journal is © The Royal Society of Chemistry 2014

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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_130929a_0m

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H18 Cl N O S'
_chemical_formula_weight         307.82

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           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

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

_cell_length_a                   6.6951(9)
_cell_length_b                   7.9252(11)
_cell_length_c                   29.888(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1585.9(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3726
_cell_measurement_theta_min      2.66
_cell_measurement_theta_max      27.00

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             648
_exptl_absorpt_coefficient_mu    0.368
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9334
_exptl_absorpt_correction_T_max  0.9783
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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 APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8276
_diffrn_reflns_av_R_equivalents  0.0205
_diffrn_reflns_av_sigmaI/netI    0.0222
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         2.66
_diffrn_reflns_theta_max         25.05
_reflns_number_total             2801
_reflns_number_gt                2651
_reflns_threshold_expression     >2sigma(I)

_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-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0354P)²+0.2205P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0096(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(7)
_refine_ls_number_reflns         2801
_refine_ls_number_parameters     185
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0306
_refine_ls_R_factor_gt           0.0284
_refine_ls_wR_factor_ref         0.0719
_refine_ls_wR_factor_gt          0.0704
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_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
S1 S 0.90384(7) 0.54006(6) 0.943122(15) 0.04522(14) Uani 1 1 d . . .
Cl1 Cl 1.05317(10) 1.02432(8) 0.904917(19) 0.0705(2) Uani 1 1 d . . .
C1 C 0.7691(3) 0.8165(3) 0.83439(6) 0.0440(5) Uani 1 1 d . . .
C2 C 0.6036(4) 0.8936(3) 0.85109(8) 0.0630(6) Uani 1 1 d . . .
H2 H 0.5822 0.8936 0.8818 0.076 Uiso 1 1 calc R . .
C3 C 0.4650(4) 0.9730(3) 0.82315(9) 0.0753(7) Uani 1 1 d . . .
H3 H 0.3541 1.0265 0.8354 0.090 Uiso 1 1 calc R . .
C4 C 0.4919(4) 0.9723(3) 0.77841(8) 0.0666(6) Uani 1 1 d . . .
H4 H 0.3959 1.0211 0.7600 0.080 Uiso 1 1 calc R . .
C5 C 0.6624(3) 0.8989(2) 0.75919(7) 0.0490(5) Uani 1 1 d . . .
C6 C 0.6979(4) 0.9005(3) 0.71255(7) 0.0629(7) Uani 1 1 d . . .
H6 H 0.6046 0.9513 0.6938 0.076 Uiso 1 1 calc R . .
C7 C 0.8606(5) 0.8316(3) 0.69455(7) 0.0660(7) Uani 1 1 d . . .
H7 H 0.8774 0.8321 0.6637 0.079 Uiso 1 1 calc R . .
C8 C 1.0072(5) 0.7580(3) 0.72211(7) 0.0647(7) Uani 1 1 d . . .
H8 H 1.1224 0.7129 0.7095 0.078 Uiso 1 1 calc R . .
C9 C 0.9800(4) 0.7528(2) 0.76747(7) 0.0511(5) Uani 1 1 d . . .
H9 H 1.0776 0.7039 0.7854 0.061 Uiso 1 1 calc R . .
C10 C 0.8072(3) 0.8201(2) 0.78740(6) 0.0421(4) Uani 1 1 d . . .
C11 C 0.9115(3) 0.7238(3) 0.86438(6) 0.0444(4) Uani 1 1 d . . .
H11 H 0.9605 0.6164 0.8524 0.053 Uiso 1 1 calc R . .
C12 C 1.0446(3) 0.8050(3) 0.89771(7) 0.0509(5) Uani 1 1 d . . .
H12 H 1.1694 0.7449 0.9040 0.061 Uiso 1 1 calc R . .
C13 C 0.6453(3) 0.4607(3) 0.94145(6) 0.0523(5) Uani 1 1 d . . .
C14 C 0.6545(4) 0.2942(3) 0.96753(9) 0.0699(7) Uani 1 1 d . . .
H14A H 0.6928 0.3165 0.9979 0.105 Uiso 1 1 calc R . .
H14B H 0.7509 0.2207 0.9539 0.105 Uiso 1 1 calc R . .
H14C H 0.5255 0.2413 0.9671 0.105 Uiso 1 1 calc R . .
C15 C 0.5150(4) 0.5884(4) 0.96610(8) 0.0760(8) Uani 1 1 d . . .
H15A H 0.5137 0.6929 0.9499 0.114 Uiso 1 1 calc R . .
H15B H 0.5680 0.6071 0.9955 0.114 Uiso 1 1 calc R . .
H15C H 0.3813 0.5456 0.9684 0.114 Uiso 1 1 calc R . .
C16 C 0.5778(4) 0.4322(4) 0.89391(8) 0.0750(7) Uani 1 1 d . . .
H16A H 0.4506 0.3762 0.8940 0.113 Uiso 1 1 calc R . .
H16B H 0.6740 0.3633 0.8786 0.113 Uiso 1 1 calc R . .
H16C H 0.5658 0.5388 0.8789 0.113 Uiso 1 1 calc R . .
N1 N 0.8645(3) 0.7223(2) 0.91288(5) 0.0458(4) Uani 1 1 d . . .
O1 O 1.0284(2) 0.42288(19) 0.91680(5) 0.0572(4) 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
S1 O1 1.4751(15) . ?
S1 N1 1.7243(16) . ?
S1 C13 1.842(2) . ?
Cl1 C12 1.752(2) . ?
C1 C2 1.360(3) . ?
C1 C10 1.428(3) . ?
C1 C11 1.500(3) . ?
C2 C3 1.398(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.349(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.404(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.414(3) . ?
C5 C10 1.428(3) . ?
C6 C7 1.332(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.408(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.368(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.407(3) . ?
C9 H9 0.9300 . ?
C11 N1 1.483(2) . ?
C11 C12 1.484(3) . ?
C11 H11 0.9800 . ?
C12 N1 1.445(3) . ?
C12 H12 0.9800 . ?
C13 C16 1.508(3) . ?
C13 C15 1.526(3) . ?
C13 C14 1.534(3) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 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
O1 S1 N1 109.52(8) . . ?
O1 S1 C13 107.55(10) . . ?
N1 S1 C13 97.37(9) . . ?
C2 C1 C10 119.83(19) . . ?
C2 C1 C11 121.21(18) . . ?
C10 C1 C11 118.95(17) . . ?
C1 C2 C3 121.6(2) . . ?
C1 C2 H2 119.2 . . ?
C3 C2 H2 119.2 . . ?
C4 C3 C2 120.1(2) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 121.1(2) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
C4 C5 C6 122.4(2) . . ?
C4 C5 C10 119.41(18) . . ?
C6 C5 C10 118.2(2) . . ?
C7 C6 C5 122.1(2) . . ?
C7 C6 H6 118.9 . . ?
C5 C6 H6 118.9 . . ?
C6 C7 C8 120.2(2) . . ?
C6 C7 H7 119.9 . . ?
C8 C7 H7 119.9 . . ?
C9 C8 C7 120.0(2) . . ?
C9 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
C8 C9 C10 121.2(2) . . ?
C8 C9 H9 119.4 . . ?
C10 C9 H9 119.4 . . ?
C9 C10 C1 123.78(18) . . ?
C9 C10 C5 118.28(17) . . ?
C1 C10 C5 117.94(19) . . ?
N1 C11 C12 58.31(12) . . ?
N1 C11 C1 116.95(16) . . ?
C12 C11 C1 124.82(19) . . ?
N1 C11 H11 114.8 . . ?
C12 C11 H11 114.8 . . ?
C1 C11 H11 114.8 . . ?
N1 C12 C11 60.83(13) . . ?
N1 C12 Cl1 115.99(15) . . ?
C11 C12 Cl1 122.15(16) . . ?
N1 C12 H12 115.5 . . ?
C11 C12 H12 115.5 . . ?
Cl1 C12 H12 115.5 . . ?
C16 C13 C15 112.5(2) . . ?
C16 C13 C14 111.2(2) . . ?
C15 C13 C14 110.36(19) . . ?
C16 C13 S1 111.01(15) . . ?
C15 C13 S1 107.33(17) . . ?
C14 C13 S1 104.03(14) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C12 N1 C11 60.86(13) . . ?
C12 N1 S1 114.64(13) . . ?
C11 N1 S1 119.12(12) . . ?

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
C10 C1 C2 C3 2.0(4) . . . . ?
C11 C1 C2 C3 -176.8(2) . . . . ?
C1 C2 C3 C4 1.0(4) . . . . ?
C2 C3 C4 C5 -2.8(4) . . . . ?
C3 C4 C5 C6 -178.1(2) . . . . ?
C3 C4 C5 C10 1.6(4) . . . . ?
C4 C5 C6 C7 179.6(2) . . . . ?
C10 C5 C6 C7 -0.1(3) . . . . ?
C5 C6 C7 C8 -1.8(3) . . . . ?
C6 C7 C8 C9 1.9(3) . . . . ?
C7 C8 C9 C10 0.0(3) . . . . ?
C8 C9 C10 C1 179.1(2) . . . . ?
C8 C9 C10 C5 -1.8(3) . . . . ?
C2 C1 C10 C9 176.0(2) . . . . ?
C11 C1 C10 C9 -5.2(3) . . . . ?
C2 C1 C10 C5 -3.1(3) . . . . ?
C11 C1 C10 C5 175.74(18) . . . . ?
C4 C5 C10 C9 -177.8(2) . . . . ?
C6 C5 C10 C9 1.9(3) . . . . ?
C4 C5 C10 C1 1.3(3) . . . . ?
C6 C5 C10 C1 -179.01(18) . . . . ?
C2 C1 C11 N1 -0.7(3) . . . . ?
C10 C1 C11 N1 -179.47(17) . . . . ?
C2 C1 C11 C12 -69.3(3) . . . . ?
C10 C1 C11 C12 111.9(2) . . . . ?
C1 C11 C12 N1 102.7(2) . . . . ?
N1 C11 C12 Cl1 -104.00(18) . . . . ?
C1 C11 C12 Cl1 -1.3(3) . . . . ?
O1 S1 C13 C16 -53.00(19) . . . . ?
N1 S1 C13 C16 60.22(18) . . . . ?
O1 S1 C13 C15 -176.34(14) . . . . ?
N1 S1 C13 C15 -63.11(15) . . . . ?
O1 S1 C13 C14 66.68(16) . . . . ?
N1 S1 C13 C14 179.90(15) . . . . ?
Cl1 C12 N1 C11 113.95(17) . . . . ?
C11 C12 N1 S1 110.93(14) . . . . ?
Cl1 C12 N1 S1 -135.12(12) . . . . ?
C1 C11 N1 C12 -116.0(2) . . . . ?
C12 C11 N1 S1 -103.64(16) . . . . ?
C1 C11 N1 S1 140.33(16) . . . . ?
O1 S1 N1 C12 -54.89(16) . . . . ?
C13 S1 N1 C12 -166.52(14) . . . . ?
O1 S1 N1 C11 14.14(17) . . . . ?
C13 S1 N1 C11 -97.48(15) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.05
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.133
_refine_diff_density_min         -0.161
_refine_diff_density_rms         0.027
_database_code_depnum_ccdc_archive 'CCDC 976642'
