# Electronic Supplementary Material (ESI) for RSC Advances
# This journal is © The Royal Society of Chemistry 2013

#######################################################################
#
#                 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_shelxl
#TrackingRef 'ns-174.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H13 Cl N2 S'
_chemical_formula_sum            'C16 H13 Cl N2 S'
_chemical_formula_weight         300.79

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'
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           monoclinic
_symmetry_space_group_name_H-M   'P 21/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                   4.2750(4)
_cell_length_b                   19.7528(15)
_cell_length_c                   17.138(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.163(9)
_cell_angle_gamma                90.00
_cell_volume                     1446.1(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2053
_cell_measurement_theta_min      3.2
_cell_measurement_theta_max      25.0

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.382
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             624
_exptl_absorpt_coefficient_mu    0.399
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9317
_exptl_absorpt_correction_T_max  0.9537
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      298(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7718
_diffrn_reflns_av_R_equivalents  0.0234
_diffrn_reflns_av_sigmaI/netI    0.0253
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.15
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2419
_reflns_number_gt                2053
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_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 F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0469P)^2^+0.4858P] where P=(Fo^2^+2Fc^2^)/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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2419
_refine_ls_number_parameters     182
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0566
_refine_ls_R_factor_gt           0.0457
_refine_ls_wR_factor_ref         0.1102
_refine_ls_wR_factor_gt          0.1045
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_restrained_S_all      1.076
_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
C1 C -0.2054(6) 0.06573(13) 0.67450(17) 0.0587(7) Uani 1 1 d . . .
C2 C -0.2046(6) 0.02944(13) 0.74239(19) 0.0690(8) Uani 1 1 d . . .
H2 H -0.3047 -0.0123 0.7439 0.083 Uiso 1 1 calc R . .
C3 C -0.0551(6) 0.05495(12) 0.80850(18) 0.0618(7) Uani 1 1 d . . .
H3 H -0.0567 0.0303 0.8547 0.074 Uiso 1 1 calc R . .
C4 C 0.0982(5) 0.11693(11) 0.80751(15) 0.0472(6) Uani 1 1 d . . .
C5 C 0.0917(6) 0.15213(12) 0.73759(16) 0.0559(7) Uani 1 1 d . . .
H5 H 0.1913 0.1939 0.7355 0.067 Uiso 1 1 calc R . .
C6 C -0.0582(6) 0.12709(12) 0.67100(17) 0.0616(7) Uani 1 1 d . . .
H6 H -0.0592 0.1515 0.6246 0.074 Uiso 1 1 calc R . .
C7 C 0.2610(5) 0.14260(11) 0.87923(15) 0.0471(6) Uani 1 1 d . . .
C8 C 0.4586(5) 0.20595(12) 0.87629(15) 0.0503(6) Uani 1 1 d . . .
H8A H 0.6622 0.1983 0.9017 0.060 Uiso 1 1 calc R . .
H8B H 0.4884 0.2193 0.8226 0.060 Uiso 1 1 calc R . .
C9 C 0.2835(5) 0.25960(11) 0.91836(16) 0.0463(6) Uani 1 1 d . . .
C10 C -0.0577(7) 0.37591(13) 0.92888(18) 0.0720(8) Uani 1 1 d . . .
H10A H -0.2065 0.3491 0.9559 0.108 Uiso 1 1 calc R . .
H10B H -0.1640 0.4127 0.9026 0.108 Uiso 1 1 calc R . .
H10C H 0.0962 0.3936 0.9657 0.108 Uiso 1 1 calc R . .
C11 C 0.3684(5) 0.20454(12) 1.03623(15) 0.0506(6) Uani 1 1 d . . .
C12 C 0.4890(6) 0.22135(15) 1.11039(16) 0.0651(7) Uani 1 1 d . . .
H12 H 0.4840 0.2663 1.1264 0.078 Uiso 1 1 calc R . .
C13 C 0.6138(8) 0.17397(18) 1.1601(2) 0.0820(9) Uani 1 1 d . . .
H13 H 0.7028 0.1867 1.2083 0.098 Uiso 1 1 calc R . .
C14 C 0.6066(8) 0.10712(19) 1.1383(2) 0.0900(11) Uani 1 1 d . . .
H14 H 0.6915 0.0743 1.1718 0.108 Uiso 1 1 calc R . .
C15 C 0.4755(8) 0.08855(15) 1.06784(19) 0.0823(9) Uani 1 1 d . . .
H15 H 0.4621 0.0428 1.0552 0.099 Uiso 1 1 calc R . .
C16 C 0.3609(6) 0.13645(12) 1.01406(15) 0.0562(6) Uani 1 1 d . . .
N1 N 0.2269(5) 0.11166(10) 0.94385(13) 0.0572(5) Uani 1 1 d . . .
N2 N 0.2463(4) 0.25860(9) 0.99183(13) 0.0493(5) Uani 1 1 d . . .
S1 S 0.13090(16) 0.32426(3) 0.85885(4) 0.0607(2) Uani 1 1 d . . .
Cl1 Cl -0.39883(19) 0.03393(4) 0.59149(5) 0.0860(3) Uani 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
C1 0.0550(14) 0.0545(14) 0.067(2) -0.0189(13) 0.0019(12) 0.0066(11)
C2 0.0679(17) 0.0502(14) 0.089(3) -0.0079(15) 0.0025(15) -0.0109(13)
C3 0.0644(16) 0.0493(13) 0.072(2) 0.0041(13) 0.0042(14) -0.0042(12)
C4 0.0462(12) 0.0409(11) 0.0553(17) -0.0034(11) 0.0122(11) 0.0029(10)
C5 0.0665(16) 0.0465(13) 0.0553(18) -0.0054(12) 0.0082(13) -0.0066(11)
C6 0.0736(17) 0.0550(14) 0.0565(19) -0.0058(12) 0.0051(14) 0.0015(13)
C7 0.0470(12) 0.0428(12) 0.0522(17) -0.0040(11) 0.0116(11) 0.0058(10)
C8 0.0429(12) 0.0601(14) 0.0484(16) 0.0007(11) 0.0069(10) -0.0053(10)
C9 0.0392(12) 0.0439(12) 0.0552(17) -0.0013(11) -0.0033(10) -0.0094(9)
C10 0.0689(17) 0.0513(14) 0.094(2) -0.0042(14) -0.0151(16) 0.0039(12)
C11 0.0451(13) 0.0606(14) 0.0465(17) 0.0013(12) 0.0060(11) 0.0050(11)
C12 0.0643(16) 0.0788(18) 0.052(2) -0.0044(14) -0.0016(13) 0.0052(14)
C13 0.083(2) 0.110(3) 0.053(2) 0.0043(18) -0.0024(15) 0.0199(18)
C14 0.112(3) 0.105(3) 0.054(2) 0.0212(19) 0.0069(18) 0.042(2)
C15 0.122(3) 0.0670(17) 0.060(2) 0.0132(15) 0.0193(18) 0.0251(17)
C16 0.0648(16) 0.0587(14) 0.0461(17) 0.0044(12) 0.0136(12) 0.0076(12)
N1 0.0728(14) 0.0477(11) 0.0517(15) 0.0025(10) 0.0129(11) 0.0033(10)
N2 0.0468(11) 0.0507(11) 0.0500(15) -0.0039(9) -0.0022(9) 0.0006(8)
S1 0.0648(4) 0.0518(4) 0.0642(5) 0.0062(3) -0.0141(3) -0.0084(3)
Cl1 0.0870(5) 0.0818(5) 0.0877(7) -0.0311(4) -0.0152(4) -0.0044(4)

_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
C1 C2 1.366(4) . ?
C1 C6 1.368(4) . ?
C1 Cl1 1.736(3) . ?
C2 C3 1.375(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.389(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.385(3) . ?
C4 C7 1.479(3) . ?
C5 C6 1.379(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 N1 1.278(3) . ?
C7 C8 1.512(3) . ?
C8 C9 1.498(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 N2 1.275(3) . ?
C9 S1 1.745(2) . ?
C10 S1 1.790(3) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.393(3) . ?
C11 C16 1.398(3) . ?
C11 N2 1.401(3) . ?
C12 C13 1.361(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.372(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.362(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.397(4) . ?
C15 H15 0.9300 . ?
C16 N1 1.401(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
C2 C1 C6 121.1(3) . . ?
C2 C1 Cl1 119.6(2) . . ?
C6 C1 Cl1 119.4(2) . . ?
C1 C2 C3 119.7(2) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 H2 120.2 . . ?
C2 C3 C4 121.2(3) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C5 C4 C3 117.3(2) . . ?
C5 C4 C7 122.7(2) . . ?
C3 C4 C7 120.0(2) . . ?
C6 C5 C4 122.0(2) . . ?
C6 C5 H5 119.0 . . ?
C4 C5 H5 119.0 . . ?
C1 C6 C5 118.8(3) . . ?
C1 C6 H6 120.6 . . ?
C5 C6 H6 120.6 . . ?
N1 C7 C4 119.4(2) . . ?
N1 C7 C8 120.5(2) . . ?
C4 C7 C8 120.1(2) . . ?
C9 C8 C7 106.22(18) . . ?
C9 C8 H8A 110.5 . . ?
C7 C8 H8A 110.5 . . ?
C9 C8 H8B 110.5 . . ?
C7 C8 H8B 110.5 . . ?
H8A C8 H8B 108.7 . . ?
N2 C9 C8 123.2(2) . . ?
N2 C9 S1 122.04(18) . . ?
C8 C9 S1 114.77(19) . . ?
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 . . ?
C12 C11 C16 118.8(2) . . ?
C12 C11 N2 115.5(2) . . ?
C16 C11 N2 125.6(2) . . ?
C13 C12 C11 122.0(3) . . ?
C13 C12 H12 119.0 . . ?
C11 C12 H12 119.0 . . ?
C12 C13 C14 119.1(3) . . ?
C12 C13 H13 120.4 . . ?
C14 C13 H13 120.4 . . ?
C15 C14 C13 120.3(3) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C14 C15 C16 121.7(3) . . ?
C14 C15 H15 119.2 . . ?
C16 C15 H15 119.2 . . ?
C15 C16 C11 117.9(3) . . ?
C15 C16 N1 116.8(2) . . ?
C11 C16 N1 125.1(2) . . ?
C7 N1 C16 121.4(2) . . ?
C9 N2 C11 119.4(2) . . ?
C9 S1 C10 101.13(13) . . ?

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
C6 C1 C2 C3 0.3(4) . . . . ?
Cl1 C1 C2 C3 -179.1(2) . . . . ?
C1 C2 C3 C4 -0.6(4) . . . . ?
C2 C3 C4 C5 0.6(4) . . . . ?
C2 C3 C4 C7 -179.1(2) . . . . ?
C3 C4 C5 C6 -0.4(4) . . . . ?
C7 C4 C5 C6 179.2(2) . . . . ?
C2 C1 C6 C5 -0.2(4) . . . . ?
Cl1 C1 C6 C5 179.3(2) . . . . ?
C4 C5 C6 C1 0.2(4) . . . . ?
C5 C4 C7 N1 171.7(2) . . . . ?
C3 C4 C7 N1 -8.6(3) . . . . ?
C5 C4 C7 C8 -6.6(3) . . . . ?
C3 C4 C7 C8 173.0(2) . . . . ?
N1 C7 C8 C9 -69.1(3) . . . . ?
C4 C7 C8 C9 109.3(2) . . . . ?
C7 C8 C9 N2 68.9(3) . . . . ?
C7 C8 C9 S1 -110.91(19) . . . . ?
C16 C11 C12 C13 3.4(4) . . . . ?
N2 C11 C12 C13 179.7(3) . . . . ?
C11 C12 C13 C14 -3.4(5) . . . . ?
C12 C13 C14 C15 -0.1(5) . . . . ?
C13 C14 C15 C16 3.6(5) . . . . ?
C14 C15 C16 C11 -3.4(5) . . . . ?
C14 C15 C16 N1 -179.1(3) . . . . ?
C12 C11 C16 C15 0.0(4) . . . . ?
N2 C11 C16 C15 -175.8(3) . . . . ?
C12 C11 C16 N1 175.3(2) . . . . ?
N2 C11 C16 N1 -0.5(4) . . . . ?
C4 C7 N1 C16 -176.0(2) . . . . ?
C8 C7 N1 C16 2.3(3) . . . . ?
C15 C16 N1 C7 -143.5(3) . . . . ?
C11 C16 N1 C7 41.2(4) . . . . ?
C8 C9 N2 C11 -1.2(3) . . . . ?
S1 C9 N2 C11 178.59(16) . . . . ?
C12 C11 N2 C9 143.2(2) . . . . ?
C16 C11 N2 C9 -40.8(3) . . . . ?
N2 C9 S1 C10 -0.3(2) . . . . ?
C8 C9 S1 C10 179.49(17) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.185
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.033


_database_code_depnum_ccdc_archive 'CCDC 920827'