# 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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#  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_thn1
#TrackingRef 'thn1.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          483K
_chemical_formula_moiety         'C16 H12 N2 O2 S'
_chemical_formula_sum            'C16 H12 N2 O2 S'
_chemical_formula_weight         296.34

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'

_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   'P n a 21'

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

_cell_length_a                   9.8800(5)
_cell_length_b                   22.9781(15)
_cell_length_c                   6.1558(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1397.51(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1006
_cell_measurement_theta_min      3.3587
_cell_measurement_theta_max      29.0865

_exptl_crystal_description       ?
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.23
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             616
_exptl_absorpt_coefficient_mu    0.237
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.96148
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(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  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4043
_diffrn_reflns_av_R_equivalents  0.0153
_diffrn_reflns_av_sigmaI/netI    0.0361
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         3.37
_diffrn_reflns_theta_max         29.15
_reflns_number_total             2693
_reflns_number_gt                2168
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_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^)+(0.0304P)^2^+0.3810P] 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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   1.11(11)
_refine_ls_number_reflns         2693
_refine_ls_number_parameters     190
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0619
_refine_ls_R_factor_gt           0.0439
_refine_ls_wR_factor_ref         0.0963
_refine_ls_wR_factor_gt          0.0852
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.064
_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
S1 S 0.10188(8) 0.65865(4) 0.44076(18) 0.0688(3) Uani 1 1 d . . .
C1 C -0.1137(2) 0.89693(12) 1.1820(4) 0.0343(6) Uani 1 1 d . . .
N1 N -0.0459(2) 0.81608(10) 0.9671(4) 0.0420(6) Uani 1 1 d . . .
O1 O 0.0654(2) 0.83932(9) 1.3335(4) 0.0599(6) Uani 1 1 d . . .
H1 H 0.0516 0.8211 1.2211 0.090 Uiso 1 1 calc R . .
C9 C -0.1958(3) 0.94856(12) 1.2004(4) 0.0365(6) Uani 1 1 d . . .
C8 C -0.2859(3) 0.96732(12) 1.0367(5) 0.0439(7) Uani 1 1 d . . .
H8 H -0.2950 0.9455 0.9103 0.053 Uiso 1 1 calc R . .
N2 N -0.0735(2) 0.77890(10) 0.7981(4) 0.0431(6) Uani 1 1 d . . .
H2 H -0.1526 0.7783 0.7399 0.052 Uiso 1 1 calc R . .
C10 C -0.1835(3) 0.98372(12) 1.3888(5) 0.0433(7) Uani 1 1 d . . .
O2 O 0.13929(17) 0.74178(10) 0.8041(3) 0.0552(6) Uani 1 1 d . . .
C12 C 0.0252(3) 0.74324(13) 0.7244(5) 0.0422(7) Uani 1 1 d . . .
C2 C -0.0196(3) 0.88499(13) 1.3438(5) 0.0429(7) Uani 1 1 d . . .
C11 C -0.1315(3) 0.85719(12) 1.0010(4) 0.0385(6) Uani 1 1 d . . .
H011 H -0.2054 0.8615 0.9089 0.046 Uiso 1 1 calc R . .
C5 C -0.2612(3) 1.03476(13) 1.4084(6) 0.0602(9) Uani 1 1 d . . .
H5 H -0.2530 1.0576 1.5325 0.072 Uiso 1 1 calc R . .
C13 C -0.0129(3) 0.70827(12) 0.5349(5) 0.0435(7) Uani 1 1 d . . .
C3 C -0.0095(3) 0.92064(14) 1.5283(5) 0.0515(8) Uani 1 1 d . . .
H3 H 0.0531 0.9117 1.6361 0.062 Uiso 1 1 calc R . .
C4 C -0.0899(3) 0.96793(15) 1.5509(5) 0.0526(8) Uani 1 1 d . . .
H4 H -0.0832 0.9905 1.6760 0.063 Uiso 1 1 calc R . .
C7 C -0.3600(3) 1.01726(14) 1.0616(6) 0.0567(8) Uani 1 1 d . . .
H7 H -0.4193 1.0287 0.9523 0.068 Uiso 1 1 calc R . .
C15 C -0.1161(3) 0.67152(16) 0.2282(7) 0.0677(10) Uani 1 1 d . . .
H017 H -0.1830 0.6676 0.1231 0.081 Uiso 1 1 calc R . .
C14 C -0.1250(3) 0.71022(15) 0.4055(6) 0.0623(10) Uani 1 1 d . . .
H018 H -0.1988 0.7343 0.4313 0.075 Uiso 1 1 calc R . .
C6 C -0.3481(4) 1.05126(16) 1.2482(7) 0.0675(10) Uani 1 1 d . . .
H6 H -0.3992 1.0850 1.2632 0.081 Uiso 1 1 calc R . .
C16 C -0.0001(3) 0.64092(16) 0.2280(6) 0.0693(11) Uani 1 1 d . . .
H020 H 0.0219 0.6132 0.1236 0.083 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
S1 0.0506(4) 0.0641(5) 0.0919(7) -0.0230(6) 0.0103(5) 0.0174(4)
C1 0.0313(12) 0.0375(15) 0.0340(14) -0.0025(13) 0.0013(11) -0.0110(11)
N1 0.0321(10) 0.0463(13) 0.0476(14) -0.0054(12) 0.0028(10) -0.0015(10)
O1 0.0480(11) 0.0664(15) 0.0652(14) 0.0000(13) -0.0180(11) 0.0057(11)
C9 0.0341(13) 0.0339(15) 0.0415(15) -0.0026(13) 0.0075(12) -0.0082(12)
C8 0.0430(15) 0.0420(16) 0.0468(16) 0.0008(15) 0.0056(14) -0.0028(14)
N2 0.0266(10) 0.0464(14) 0.0563(15) -0.0144(12) -0.0023(11) 0.0046(10)
C10 0.0446(15) 0.0441(16) 0.0411(16) -0.0058(14) 0.0143(13) -0.0142(13)
O2 0.0297(9) 0.0686(15) 0.0673(14) -0.0041(12) -0.0023(10) 0.0091(10)
C12 0.0311(13) 0.0390(16) 0.0564(17) 0.0013(15) 0.0086(13) -0.0007(12)
C2 0.0354(14) 0.0473(17) 0.0462(16) 0.0056(15) -0.0007(13) -0.0086(13)
C11 0.0313(13) 0.0417(16) 0.0426(17) -0.0012(13) -0.0010(11) -0.0027(12)
C5 0.068(2) 0.0507(19) 0.061(2) -0.0177(19) 0.022(2) -0.0093(16)
C13 0.0344(14) 0.0323(14) 0.0638(17) -0.0077(15) 0.0121(14) -0.0006(12)
C3 0.0473(17) 0.068(2) 0.0390(15) 0.0020(17) -0.0081(14) -0.0166(16)
C4 0.0587(19) 0.060(2) 0.0393(16) -0.0132(16) 0.0092(15) -0.0224(17)
C7 0.0542(18) 0.051(2) 0.065(2) 0.0055(19) 0.0045(16) 0.0080(16)
C15 0.0487(18) 0.069(2) 0.085(3) -0.035(2) 0.0031(18) -0.0070(18)
C14 0.0434(16) 0.0586(19) 0.085(3) -0.032(2) 0.0007(19) 0.0035(15)
C6 0.065(2) 0.051(2) 0.086(3) -0.007(2) 0.021(2) 0.0095(18)
C16 0.058(2) 0.063(2) 0.086(3) -0.035(2) 0.0201(19) -0.0013(18)

_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 C16 1.702(4) . ?
S1 C13 1.709(3) . ?
C1 C2 1.389(4) . ?
C1 C9 1.442(4) . ?
C1 C11 1.451(4) . ?
N1 C11 1.285(3) . ?
N1 N2 1.374(3) . ?
O1 C2 1.346(3) . ?
O1 H1 0.8200 . ?
C9 C8 1.412(4) . ?
C9 C10 1.418(4) . ?
C8 C7 1.370(4) . ?
C8 H8 0.9300 . ?
N2 C12 1.352(3) . ?
N2 H2 0.8600 . ?
C10 C5 1.407(4) . ?
C10 C4 1.408(4) . ?
O2 C12 1.229(3) . ?
C12 C13 1.466(4) . ?
C2 C3 1.404(4) . ?
C11 H011 0.9300 . ?
C5 C6 1.361(5) . ?
C5 H5 0.9300 . ?
C13 C14 1.364(4) . ?
C3 C4 1.353(4) . ?
C3 H3 0.9300 . ?
C4 H4 0.9300 . ?
C7 C6 1.394(5) . ?
C7 H7 0.9300 . ?
C15 C16 1.344(5) . ?
C15 C14 1.411(5) . ?
C15 H017 0.9300 . ?
C14 H018 0.9300 . ?
C6 H6 0.9300 . ?
C16 H020 0.9300 . ?

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
C16 S1 C13 91.59(17) . . ?
C2 C1 C9 118.9(2) . . ?
C2 C1 C11 120.5(3) . . ?
C9 C1 C11 120.6(2) . . ?
C11 N1 N2 116.7(2) . . ?
C2 O1 H1 109.5 . . ?
C8 C9 C10 117.6(3) . . ?
C8 C9 C1 123.4(2) . . ?
C10 C9 C1 119.0(2) . . ?
C7 C8 C9 120.8(3) . . ?
C7 C8 H8 119.6 . . ?
C9 C8 H8 119.6 . . ?
C12 N2 N1 119.2(2) . . ?
C12 N2 H2 120.4 . . ?
N1 N2 H2 120.4 . . ?
C5 C10 C4 120.8(3) . . ?
C5 C10 C9 119.9(3) . . ?
C4 C10 C9 119.3(3) . . ?
O2 C12 N2 122.9(3) . . ?
O2 C12 C13 122.6(3) . . ?
N2 C12 C13 114.4(2) . . ?
O1 C2 C1 122.5(3) . . ?
O1 C2 C3 116.6(3) . . ?
C1 C2 C3 120.8(3) . . ?
N1 C11 C1 120.5(2) . . ?
N1 C11 H011 119.8 . . ?
C1 C11 H011 119.8 . . ?
C6 C5 C10 121.0(3) . . ?
C6 C5 H5 119.5 . . ?
C10 C5 H5 119.5 . . ?
C14 C13 C12 130.9(3) . . ?
C14 C13 S1 111.3(2) . . ?
C12 C13 S1 117.7(2) . . ?
C4 C3 C2 120.6(3) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C10 121.3(3) . . ?
C3 C4 H4 119.3 . . ?
C10 C4 H4 119.3 . . ?
C8 C7 C6 121.1(3) . . ?
C8 C7 H7 119.5 . . ?
C6 C7 H7 119.5 . . ?
C16 C15 C14 112.6(3) . . ?
C16 C15 H017 123.7 . . ?
C14 C15 H017 123.7 . . ?
C13 C14 C15 112.3(3) . . ?
C13 C14 H018 123.8 . . ?
C15 C14 H018 123.8 . . ?
C5 C6 C7 119.6(3) . . ?
C5 C6 H6 120.2 . . ?
C7 C6 H6 120.2 . . ?
C15 C16 S1 112.2(3) . . ?
C15 C16 H020 123.9 . . ?
S1 C16 H020 123.9 . . ?

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
C2 C1 C9 C8 174.4(2) . . . . ?
C11 C1 C9 C8 -7.3(4) . . . . ?
C2 C1 C9 C10 -3.6(4) . . . . ?
C11 C1 C9 C10 174.7(2) . . . . ?
C10 C9 C8 C7 -1.0(4) . . . . ?
C1 C9 C8 C7 -179.0(3) . . . . ?
C11 N1 N2 C12 165.6(3) . . . . ?
C8 C9 C10 C5 0.9(4) . . . . ?
C1 C9 C10 C5 179.0(2) . . . . ?
C8 C9 C10 C4 -177.0(2) . . . . ?
C1 C9 C10 C4 1.2(4) . . . . ?
N1 N2 C12 O2 1.2(4) . . . . ?
N1 N2 C12 C13 -176.2(2) . . . . ?
C9 C1 C2 O1 -176.7(2) . . . . ?
C11 C1 C2 O1 5.1(4) . . . . ?
C9 C1 C2 C3 3.5(4) . . . . ?
C11 C1 C2 C3 -174.7(2) . . . . ?
N2 N1 C11 C1 177.2(2) . . . . ?
C2 C1 C11 N1 -12.1(4) . . . . ?
C9 C1 C11 N1 169.7(2) . . . . ?
C4 C10 C5 C6 177.5(3) . . . . ?
C9 C10 C5 C6 -0.3(4) . . . . ?
O2 C12 C13 C14 -168.9(3) . . . . ?
N2 C12 C13 C14 8.5(5) . . . . ?
O2 C12 C13 S1 6.6(4) . . . . ?
N2 C12 C13 S1 -176.0(2) . . . . ?
C16 S1 C13 C14 0.2(3) . . . . ?
C16 S1 C13 C12 -176.1(2) . . . . ?
O1 C2 C3 C4 179.2(3) . . . . ?
C1 C2 C3 C4 -1.0(4) . . . . ?
C2 C3 C4 C10 -1.6(4) . . . . ?
C5 C10 C4 C3 -176.4(3) . . . . ?
C9 C10 C4 C3 1.4(4) . . . . ?
C9 C8 C7 C6 0.5(5) . . . . ?
C12 C13 C14 C15 175.1(3) . . . . ?
S1 C13 C14 C15 -0.6(4) . . . . ?
C16 C15 C14 C13 0.8(5) . . . . ?
C10 C5 C6 C7 -0.3(5) . . . . ?
C8 C7 C6 C5 0.2(5) . . . . ?
C14 C15 C16 S1 -0.6(5) . . . . ?
C13 S1 C16 C15 0.2(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.847
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.145
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.039


_database_code_depnum_ccdc_archive 'CCDC 909595'