# 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
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  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_mo_120317lt_0m
#TrackingRef 'web_deposit_cif_file_0_BharatD.Narhe_1364293409.mo_120317lt_0m.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H21 N3 O2 S'
_chemical_formula_weight         343.44

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           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_symmetry_space_group_name_hall  '-P 2yn'

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                   8.8513(5)
_cell_length_b                   16.5170(9)
_cell_length_c                   11.4378(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.8400(10)
_cell_angle_gamma                90.00
_cell_volume                     1666.21(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5222
_cell_measurement_theta_min      2.4662
_cell_measurement_theta_max      26.4253

_exptl_crystal_description       Tabullar
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             728
_exptl_absorpt_coefficient_mu    0.210
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9018
_exptl_absorpt_correction_T_max  0.9486
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(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       '\f and \w scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            13993
_diffrn_reflns_av_R_equivalents  0.0274
_diffrn_reflns_av_sigmaI/netI    0.0230
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.17
_diffrn_reflns_theta_max         26.47
_reflns_number_total             3421
_reflns_number_gt                2900
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker AXS, 2010)'
_computing_cell_refinement       'SAINT V7.68A (Bruker AXS, 2009)'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXTL

_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^)+(0.0380P)^2^+0.8882P] 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         3421
_refine_ls_number_parameters     220
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0402
_refine_ls_R_factor_gt           0.0319
_refine_ls_wR_factor_ref         0.0830
_refine_ls_wR_factor_gt          0.0783
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_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 -0.18191(4) 0.01480(2) 0.79718(3) 0.01716(10) Uani 1 1 d . . .
O1 O 0.23719(12) 0.61326(6) 0.94743(10) 0.0221(2) Uani 1 1 d . . .
O2 O 0.03366(12) 0.59399(6) 0.82010(9) 0.0214(2) Uani 1 1 d . . .
N1 N -0.00816(14) 0.27790(7) 0.82531(11) 0.0167(3) Uani 1 1 d . . .
C18 C -0.03847(17) -0.14960(9) 0.73520(14) 0.0208(3) Uani 1 1 d . . .
H18A H -0.1440 -0.1496 0.7550 0.031 Uiso 1 1 calc R . .
H18B H 0.0003 -0.2052 0.7375 0.031 Uiso 1 1 calc R . .
H18C H -0.0332 -0.1273 0.6563 0.031 Uiso 1 1 calc R . .
N3 N 0.18829(13) 0.23215(7) 0.94566(10) 0.0151(3) Uani 1 1 d . . .
N2 N -0.25948(14) 0.17229(7) 0.80090(11) 0.0188(3) Uani 1 1 d . . .
H2A H -0.2405 0.2241 0.8128 0.023 Uiso 1 1 calc R . .
H2B H -0.3525 0.1561 0.7799 0.023 Uiso 1 1 calc R . .
C1 C 0.2206(2) 0.69904(9) 0.92540(15) 0.0265(4) Uani 1 1 d . . .
H1A H 0.2444 0.7109 0.8450 0.040 Uiso 1 1 calc R . .
H1B H 0.2902 0.7290 0.9808 0.040 Uiso 1 1 calc R . .
H1C H 0.1161 0.7154 0.9354 0.040 Uiso 1 1 calc R . .
C2 C 0.13399(16) 0.56631(9) 0.88720(12) 0.0164(3) Uani 1 1 d . . .
C3 C 0.15748(16) 0.47879(8) 0.91048(12) 0.0154(3) Uani 1 1 d . . .
C4 C 0.05312(16) 0.42559(8) 0.85366(12) 0.0156(3) Uani 1 1 d . . .
H4 H -0.0305 0.4451 0.8041 0.019 Uiso 1 1 calc R . .
C5 C 0.07549(15) 0.34316(9) 0.87184(12) 0.0152(3) Uani 1 1 d . . .
C6 C 0.06238(16) 0.21269(9) 0.87035(12) 0.0155(3) Uani 1 1 d . . .
C7 C 0.00768(16) 0.13081(8) 0.84729(12) 0.0153(3) Uani 1 1 d . . .
C8 C 0.09292(16) 0.05629(9) 0.85082(13) 0.0173(3) Uani 1 1 d . . .
H8 H 0.1997 0.0546 0.8687 0.021 Uiso 1 1 calc R . .
C9 C 0.00882(16) -0.01093(9) 0.82665(12) 0.0167(3) Uani 1 1 d . . .
C10 C 0.05738(17) -0.09779(9) 0.82378(13) 0.0200(3) Uani 1 1 d . . .
H10A H 0.0525 -0.1214 0.9030 0.024 Uiso 1 1 calc R . .
H10B H 0.1644 -0.1000 0.8048 0.024 Uiso 1 1 calc R . .
C11 C 0.28056(16) 0.45013(9) 0.98522(12) 0.0167(3) Uani 1 1 d . . .
H11 H 0.3496 0.4879 1.0229 0.020 Uiso 1 1 calc R . .
C12 C 0.30309(16) 0.36820(9) 1.00498(12) 0.0169(3) Uani 1 1 d . . .
H12 H 0.3854 0.3487 1.0560 0.020 Uiso 1 1 calc R . .
C13 C 0.19922(16) 0.31557(8) 0.94643(12) 0.0147(3) Uani 1 1 d . . .
C14 C -0.14435(16) 0.11703(8) 0.81502(12) 0.0151(3) Uani 1 1 d . . .
C15 C 0.28964(16) 0.17891(8) 1.01838(12) 0.0155(3) Uani 1 1 d . . .
H15A H 0.2359 0.1278 1.0326 0.019 Uiso 1 1 calc R . .
H15B H 0.3154 0.2052 1.0953 0.019 Uiso 1 1 calc R . .
C16 C 0.43539(16) 0.15951(9) 0.96239(12) 0.0171(3) Uani 1 1 d . . .
H16A H 0.4109 0.1291 0.8887 0.020 Uiso 1 1 calc R . .
H16B H 0.4861 0.2106 0.9427 0.020 Uiso 1 1 calc R . .
C17 C 0.54219(17) 0.10965(9) 1.04476(13) 0.0216(3) Uani 1 1 d . . .
H17A H 0.5717 0.1412 1.1156 0.032 Uiso 1 1 calc R . .
H17B H 0.6328 0.0957 1.0054 0.032 Uiso 1 1 calc R . .
H17C H 0.4909 0.0599 1.0664 0.032 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 0.01514(18) 0.01378(17) 0.0220(2) 0.00020(14) -0.00159(13) -0.00168(13)
O1 0.0251(6) 0.0130(5) 0.0268(6) 0.0001(4) -0.0061(4) -0.0027(4)
O2 0.0208(5) 0.0181(5) 0.0244(6) 0.0021(4) -0.0037(4) 0.0010(4)
N1 0.0158(6) 0.0144(6) 0.0195(6) -0.0004(5) -0.0002(5) -0.0012(5)
C18 0.0210(8) 0.0170(7) 0.0245(8) -0.0030(6) 0.0031(6) -0.0015(6)
N3 0.0134(6) 0.0141(6) 0.0174(6) 0.0003(5) -0.0005(5) -0.0006(4)
N2 0.0130(6) 0.0146(6) 0.0284(7) -0.0023(5) -0.0010(5) 0.0000(5)
C1 0.0334(9) 0.0136(7) 0.0312(9) 0.0000(6) -0.0045(7) -0.0048(6)
C2 0.0168(7) 0.0169(7) 0.0156(7) -0.0019(5) 0.0029(5) -0.0015(5)
C3 0.0157(7) 0.0157(7) 0.0153(7) -0.0005(5) 0.0033(5) 0.0002(5)
C4 0.0142(7) 0.0163(7) 0.0162(7) 0.0000(5) 0.0002(5) 0.0014(5)
C5 0.0132(7) 0.0167(7) 0.0155(7) -0.0015(5) 0.0014(5) -0.0012(5)
C6 0.0133(7) 0.0165(7) 0.0167(7) -0.0004(5) 0.0019(5) -0.0004(5)
C7 0.0158(7) 0.0145(7) 0.0156(7) 0.0002(5) 0.0011(5) -0.0007(5)
C8 0.0151(7) 0.0177(7) 0.0189(7) -0.0004(6) -0.0010(5) 0.0002(5)
C9 0.0153(7) 0.0172(7) 0.0170(7) 0.0000(5) -0.0014(5) 0.0008(5)
C10 0.0203(7) 0.0152(7) 0.0241(8) -0.0002(6) -0.0010(6) 0.0008(6)
C11 0.0159(7) 0.0175(7) 0.0167(7) -0.0027(6) 0.0012(5) -0.0021(5)
C12 0.0152(7) 0.0190(7) 0.0162(7) 0.0001(6) -0.0008(5) 0.0007(5)
C13 0.0144(7) 0.0143(7) 0.0158(7) 0.0004(5) 0.0032(5) 0.0001(5)
C14 0.0168(7) 0.0149(7) 0.0135(7) 0.0000(5) 0.0015(5) -0.0014(5)
C15 0.0157(7) 0.0152(7) 0.0151(7) 0.0019(5) -0.0006(5) 0.0014(5)
C16 0.0152(7) 0.0189(7) 0.0169(7) 0.0013(6) 0.0000(5) -0.0002(5)
C17 0.0200(7) 0.0229(8) 0.0216(8) 0.0027(6) 0.0001(6) 0.0051(6)

_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 C14 1.7297(14) . ?
S1 C9 1.7460(15) . ?
O1 C2 1.3431(17) . ?
O1 C1 1.4444(18) . ?
O2 C2 1.2132(18) . ?
N1 C6 1.3270(18) . ?
N1 C5 1.3881(18) . ?
C18 C10 1.528(2) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
N3 C13 1.3813(18) . ?
N3 C6 1.3876(18) . ?
N3 C15 1.4643(17) . ?
N2 C14 1.3674(18) . ?
N2 H2A 0.8800 . ?
N2 H2B 0.8800 . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.481(2) . ?
C3 C4 1.395(2) . ?
C3 C11 1.409(2) . ?
C4 C5 1.389(2) . ?
C4 H4 0.9500 . ?
C5 C13 1.4061(19) . ?
C6 C7 1.4531(19) . ?
C7 C14 1.384(2) . ?
C7 C8 1.442(2) . ?
C8 C9 1.352(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.499(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.384(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.395(2) . ?
C12 H12 0.9500 . ?
C15 C16 1.522(2) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.5196(19) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?

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
C14 S1 C9 92.39(7) . . ?
C2 O1 C1 114.98(12) . . ?
C6 N1 C5 105.26(12) . . ?
C10 C18 H18A 109.5 . . ?
C10 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C10 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C13 N3 C6 106.69(11) . . ?
C13 N3 C15 123.80(12) . . ?
C6 N3 C15 129.42(12) . . ?
C14 N2 H2A 120.0 . . ?
C14 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O2 C2 O1 122.47(13) . . ?
O2 C2 C3 124.44(13) . . ?
O1 C2 C3 113.09(12) . . ?
C4 C3 C11 121.25(13) . . ?
C4 C3 C2 116.97(13) . . ?
C11 C3 C2 121.78(13) . . ?
C5 C4 C3 117.85(13) . . ?
C5 C4 H4 121.1 . . ?
C3 C4 H4 121.1 . . ?
N1 C5 C4 129.72(13) . . ?
N1 C5 C13 110.12(12) . . ?
C4 C5 C13 120.16(13) . . ?
N1 C6 N3 112.33(12) . . ?
N1 C6 C7 123.11(13) . . ?
N3 C6 C7 124.48(13) . . ?
C14 C7 C8 111.20(12) . . ?
C14 C7 C6 120.20(13) . . ?
C8 C7 C6 128.58(13) . . ?
C9 C8 C7 114.66(13) . . ?
C9 C8 H8 122.7 . . ?
C7 C8 H8 122.7 . . ?
C8 C9 C10 129.53(13) . . ?
C8 C9 S1 110.25(11) . . ?
C10 C9 S1 120.21(11) . . ?
C9 C10 C18 113.98(12) . . ?
C9 C10 H10A 108.8 . . ?
C18 C10 H10A 108.8 . . ?
C9 C10 H10B 108.8 . . ?
C18 C10 H10B 108.8 . . ?
H10A C10 H10B 107.7 . . ?
C12 C11 C3 121.41(13) . . ?
C12 C11 H11 119.3 . . ?
C3 C11 H11 119.3 . . ?
C11 C12 C13 116.80(13) . . ?
C11 C12 H12 121.6 . . ?
C13 C12 H12 121.6 . . ?
N3 C13 C12 131.89(13) . . ?
N3 C13 C5 105.59(12) . . ?
C12 C13 C5 122.52(13) . . ?
N2 C14 C7 128.31(13) . . ?
N2 C14 S1 120.25(11) . . ?
C7 C14 S1 111.41(11) . . ?
N3 C15 C16 112.82(11) . . ?
N3 C15 H15A 109.0 . . ?
C16 C15 H15A 109.0 . . ?
N3 C15 H15B 109.0 . . ?
C16 C15 H15B 109.0 . . ?
H15A C15 H15B 107.8 . . ?
C17 C16 C15 110.99(12) . . ?
C17 C16 H16A 109.4 . . ?
C15 C16 H16A 109.4 . . ?
C17 C16 H16B 109.4 . . ?
C15 C16 H16B 109.4 . . ?
H16A C16 H16B 108.0 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        26.47
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.326
_refine_diff_density_min         -0.401
_refine_diff_density_rms         0.045


_database_code_depnum_ccdc_archive 'CCDC 877845'