# Electronic Supplementary Material (ESI) for RSC Advances
# This journal is © The Royal Society of Chemistry 2012


data_global
_journal_name_full               'Green Chemistry'
_journal_coden_cambridge         1048
_publ_contact_author_email       bcranu@gmail.com
_publ_contact_author_name        'Brindaban C. Ranu'
loop_
_publ_author_name
B.Ranu
'Sabir Ahammed'
'Amit Saha'

data_ww
_database_code_depnum_ccdc_archive 'CCDC 861311'
#TrackingRef 'WW.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H15 N S3'
_chemical_formula_weight         269.43

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/n '

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

_cell_length_a                   7.7884(5)
_cell_length_b                   5.9160(4)
_cell_length_c                   28.2073(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.2610(10)
_cell_angle_gamma                90.00
_cell_volume                     1294.21(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5012
_cell_measurement_theta_min      2.66
_cell_measurement_theta_max      28.33

_exptl_crystal_description       PLATE
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             568
_exptl_absorpt_coefficient_mu    0.545
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.9083
_exptl_absorpt_correction_T_max  0.9475
_exptl_absorpt_process_details   SADABS

_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  ?
_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            11450
_diffrn_reflns_av_R_equivalents  0.0313
_diffrn_reflns_av_sigmaI/netI    0.0203
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         1.45
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2272
_reflns_number_gt                2032
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    PLATON
_computing_publication_material  'MERCURY 2.3'

_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^)+(0.0345P)^2^+0.6427P] 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         2272
_refine_ls_number_parameters     145
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0324
_refine_ls_R_factor_gt           0.0280
_refine_ls_wR_factor_ref         0.0743
_refine_ls_wR_factor_gt          0.0715
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.069
_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
C1 C 0.3915(2) 0.4600(3) 0.27745(6) 0.0327(4) Uani 1 1 d . . .
H1 H 0.3266 0.3494 0.2910 0.039 Uiso 1 1 calc R . .
C2 C 0.4396(2) 0.6558(3) 0.29901(7) 0.0326(4) Uani 1 1 d . . .
H2 H 0.4121 0.6938 0.3294 0.039 Uiso 1 1 calc R . .
C3 C 0.5365(2) 0.7994(3) 0.27105(6) 0.0268(4) Uani 1 1 d . . .
H3 H 0.5779 0.9410 0.2808 0.032 Uiso 1 1 calc R . .
C4 C 0.5615(2) 0.7022(3) 0.22748(6) 0.0257(4) Uani 1 1 d . . .
C6 C 0.6906(2) 0.6938(3) 0.15049(6) 0.0295(4) Uani 1 1 d . . .
H6 H 0.6540 0.5451 0.1459 0.035 Uiso 1 1 calc R . .
C5 C 0.6534(2) 0.7980(3) 0.18986(6) 0.0278(4) Uani 1 1 d . . .
H5 H 0.6898 0.9471 0.1937 0.033 Uiso 1 1 calc R . .
C7 C 0.7876(2) 0.7998(3) 0.11300(7) 0.0347(4) Uani 1 1 d . . .
H7A H 0.7933 0.9618 0.1182 0.042 Uiso 1 1 calc R . .
H7B H 0.7258 0.7733 0.0821 0.042 Uiso 1 1 calc R . .
C9 C 1.1479(3) 0.1566(3) 0.03734(7) 0.0344(4) Uani 1 1 d . . .
H9A H 1.1119 0.1965 0.0046 0.041 Uiso 1 1 calc R . .
H9B H 1.0794 0.0298 0.0466 0.041 Uiso 1 1 calc R . .
C10 C 1.3386(3) 0.1011(4) 0.04361(7) 0.0424(5) Uani 1 1 d . . .
H10A H 1.3997 0.1762 0.0196 0.051 Uiso 1 1 calc R . .
H10B H 1.3573 -0.0606 0.0416 0.051 Uiso 1 1 calc R . .
C11 C 1.3972(3) 0.1890(3) 0.09301(7) 0.0376(5) Uani 1 1 d . . .
H11B H 1.3672 0.0847 0.1175 0.045 Uiso 1 1 calc R . .
H11A H 1.5207 0.2152 0.0966 0.045 Uiso 1 1 calc R . .
C12 C 1.2983(2) 0.4079(3) 0.09487(6) 0.0308(4) Uani 1 1 d . . .
H12A H 1.2852 0.4521 0.1275 0.037 Uiso 1 1 calc R . .
H12B H 1.3548 0.5289 0.0791 0.037 Uiso 1 1 calc R . .
C8 C 0.9834(2) 0.4559(3) 0.07326(6) 0.0285(4) Uani 1 1 d . . .
N1 N 1.13122(19) 0.3510(3) 0.06928(5) 0.0276(3) Uani 1 1 d . . .
S1 S 0.46398(6) 0.43922(8) 0.222276(16) 0.03192(14) Uani 1 1 d . . .
S2 S 1.00485(6) 0.68860(8) 0.113101(16) 0.03083(14) Uani 1 1 d . . .
S3 S 0.79724(6) 0.37472(10) 0.044169(18) 0.03897(15) 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 0.0254(9) 0.0436(12) 0.0296(10) 0.0072(9) 0.0054(8) -0.0013(8)
C2 0.0266(9) 0.0431(12) 0.0290(10) -0.0015(8) 0.0066(8) 0.0065(8)
C3 0.0206(8) 0.0292(10) 0.0308(9) 0.0003(7) 0.0026(7) 0.0041(7)
C4 0.0194(8) 0.0264(10) 0.0311(9) 0.0005(7) 0.0009(7) 0.0009(7)
C6 0.0248(9) 0.0316(10) 0.0323(10) 0.0038(8) 0.0033(7) 0.0000(8)
C5 0.0209(8) 0.0259(9) 0.0367(10) 0.0036(8) 0.0025(7) 0.0004(7)
C7 0.0293(10) 0.0397(11) 0.0358(10) 0.0084(9) 0.0072(8) 0.0050(8)
C9 0.0458(11) 0.0299(10) 0.0282(10) -0.0024(8) 0.0070(8) -0.0093(9)
C10 0.0463(12) 0.0380(12) 0.0449(12) -0.0075(9) 0.0154(10) -0.0014(10)
C11 0.0310(10) 0.0404(12) 0.0421(11) 0.0007(9) 0.0078(9) 0.0023(9)
C12 0.0263(9) 0.0371(11) 0.0290(9) -0.0022(8) 0.0039(8) -0.0039(8)
C8 0.0306(10) 0.0327(10) 0.0226(9) 0.0084(7) 0.0051(7) -0.0064(8)
N1 0.0287(8) 0.0326(8) 0.0219(7) -0.0004(6) 0.0039(6) -0.0043(7)
S1 0.0332(3) 0.0335(3) 0.0293(3) -0.00080(19) 0.00408(19) -0.0076(2)
S2 0.0270(2) 0.0351(3) 0.0311(3) 0.00009(19) 0.00642(18) -0.00087(19)
S3 0.0304(3) 0.0493(3) 0.0362(3) 0.0052(2) -0.0026(2) -0.0108(2)

_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 1.346(3) . ?
C1 S1 1.7079(18) . ?
C1 H1 0.9300 . ?
C2 C3 1.422(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.387(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.449(2) . ?
C4 S1 1.7316(18) . ?
C6 C5 1.326(3) . ?
C6 C7 1.493(3) . ?
C6 H6 0.9300 . ?
C5 H5 0.9300 . ?
C7 S2 1.8151(19) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C9 N1 1.474(2) . ?
C9 C10 1.516(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.518(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.510(3) . ?
C11 H11B 0.9700 . ?
C11 H11A 0.9700 . ?
C12 N1 1.468(2) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C8 N1 1.322(2) . ?
C8 S3 1.6696(18) . ?
C8 S2 1.7754(19) . ?

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 S1 111.84(14) . . ?
C2 C1 H1 124.1 . . ?
S1 C1 H1 124.1 . . ?
C1 C2 C3 113.80(17) . . ?
C1 C2 H2 123.1 . . ?
C3 C2 H2 123.1 . . ?
C4 C3 C2 111.65(17) . . ?
C4 C3 H3 124.2 . . ?
C2 C3 H3 124.2 . . ?
C3 C4 C5 127.30(17) . . ?
C3 C4 S1 110.56(13) . . ?
C5 C4 S1 122.13(14) . . ?
C5 C6 C7 124.19(18) . . ?
C5 C6 H6 117.9 . . ?
C7 C6 H6 117.9 . . ?
C6 C5 C4 126.33(17) . . ?
C6 C5 H5 116.8 . . ?
C4 C5 H5 116.8 . . ?
C6 C7 S2 112.26(13) . . ?
C6 C7 H7A 109.2 . . ?
S2 C7 H7A 109.2 . . ?
C6 C7 H7B 109.2 . . ?
S2 C7 H7B 109.2 . . ?
H7A C7 H7B 107.9 . . ?
N1 C9 C10 103.78(15) . . ?
N1 C9 H9A 111.0 . . ?
C10 C9 H9A 111.0 . . ?
N1 C9 H9B 111.0 . . ?
C10 C9 H9B 111.0 . . ?
H9A C9 H9B 109.0 . . ?
C9 C10 C11 104.00(16) . . ?
C9 C10 H10A 111.0 . . ?
C11 C10 H10A 111.0 . . ?
C9 C10 H10B 111.0 . . ?
C11 C10 H10B 111.0 . . ?
H10A C10 H10B 109.0 . . ?
C12 C11 C10 102.36(16) . . ?
C12 C11 H11B 111.3 . . ?
C10 C11 H11B 111.3 . . ?
C12 C11 H11A 111.3 . . ?
C10 C11 H11A 111.3 . . ?
H11B C11 H11A 109.2 . . ?
N1 C12 C11 102.62(15) . . ?
N1 C12 H12A 111.2 . . ?
C11 C12 H12A 111.2 . . ?
N1 C12 H12B 111.2 . . ?
C11 C12 H12B 111.2 . . ?
H12A C12 H12B 109.2 . . ?
N1 C8 S3 123.18(15) . . ?
N1 C8 S2 112.68(13) . . ?
S3 C8 S2 124.14(11) . . ?
C8 N1 C12 126.19(15) . . ?
C8 N1 C9 122.98(15) . . ?
C12 N1 C9 110.83(14) . . ?
C1 S1 C4 92.13(9) . . ?
C8 S2 C7 104.27(9) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.298
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.044