# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2014

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#                                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.
#
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#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
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#  except for the purpose of generating routine backup copies
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#  data retrieval see:
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#  from this site to visualise CIF-encoded structures and 
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data_mo_fs329_0m

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H12 N2 S'
_chemical_formula_sum            'C19 H12 N2 S'
_chemical_formula_weight         300.37

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_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 21/c'

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                   10.2235(9)
_cell_length_b                   12.4997(11)
_cell_length_c                   11.191(1)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.6620(15)
_cell_angle_gamma                90.00
_cell_volume                     1405.4(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    294
_cell_measurement_reflns_used    5130
_cell_measurement_theta_min      2.47
_cell_measurement_theta_max      25.97
_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_min          0.315
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_max          0.603
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.420
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             624
_exptl_absorpt_coefficient_mu    0.227
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8753
_exptl_absorpt_correction_T_max  0.9320
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'

_exptl_special_details           
; 
?
;

_diffrn_ambient_temperature      294
_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 SMART APEX II DUO CCD area-detector diffractometer 
;
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10355
_diffrn_reflns_av_R_equivalents  0.0205
_diffrn_reflns_av_sigmaI/netI    0.0192
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.03
_diffrn_reflns_theta_max         25.99
_reflns_number_total             2742
_reflns_number_gt                2346
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  SHELXTL
_computing_molecular_graphics    SHELXTL
_computing_publication_material  'SHELXTL and PLATON (Spek, 2009)'


_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)+(0.0748P)²+0.3074P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2742
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0465
_refine_ls_R_factor_gt           0.0401
_refine_ls_wR_factor_ref         0.1237
_refine_ls_wR_factor_gt          0.1161
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.001

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 -0.09463(4) -0.20517(4) 0.22494(4) 0.05450(19) Uani 1 1 d . . .
N1 N 0.04575(13) -0.05634(11) 0.15055(13) 0.0472(3) Uani 1 1 d . . .
N2 N -0.11172(17) -0.13195(14) -0.00610(15) 0.0625(4) Uani 1 1 d . . .
H1N2 H -0.1912 -0.1557 -0.0166 0.075 Uiso 1 1 d R . .
H2N2 H -0.0979 -0.0732 -0.0494 0.075 Uiso 1 1 d R . .
C1 C 0.76686(19) 0.16979(15) 0.34748(19) 0.0600(5) Uani 1 1 d . . .
H1A H 0.8322 0.2155 0.3879 0.072 Uiso 1 1 calc R . .
C2 C 0.79179(19) 0.11267(16) 0.2494(2) 0.0598(5) Uani 1 1 d . . .
H2A H 0.8738 0.1186 0.2254 0.072 Uiso 1 1 calc R . .
C3 C 0.69492(17) 0.04644(15) 0.18666(17) 0.0536(4) Uani 1 1 d . . .
H3A H 0.7123 0.0079 0.1202 0.064 Uiso 1 1 calc R . .
C4 C 0.57111(16) 0.03646(13) 0.22146(15) 0.0444(4) Uani 1 1 d . . .
C5 C 0.46904(17) -0.03213(14) 0.15906(15) 0.0496(4) Uani 1 1 d . . .
H5A H 0.4850 -0.0713 0.0926 0.060 Uiso 1 1 calc R . .
C6 C 0.35045(17) -0.04155(13) 0.19386(15) 0.0474(4) Uani 1 1 d . . .
H6A H 0.2864 -0.0862 0.1498 0.057 Uiso 1 1 calc R . .
C7 C 0.31938(16) 0.01505(12) 0.29687(14) 0.0409(3) Uani 1 1 d . . .
C8 C 0.42045(16) 0.08237(12) 0.36285(14) 0.0412(4) Uani 1 1 d . . .
C9 C 0.54507(16) 0.09398(12) 0.32363(14) 0.0427(4) Uani 1 1 d . . .
C10 C 0.64586(18) 0.16134(13) 0.38851(16) 0.0514(4) Uani 1 1 d . . .
C11 C 0.6199(2) 0.21458(15) 0.49425(18) 0.0615(5) Uani 1 1 d . . .
H11A H 0.6849 0.2593 0.5370 0.074 Uiso 1 1 calc R . .
C12 C 0.5049(2) 0.20235(14) 0.53420(17) 0.0603(5) Uani 1 1 d . . .
H12A H 0.4925 0.2379 0.6043 0.072 Uiso 1 1 calc R . .
C13 C 0.39976(18) 0.13483(13) 0.47009(15) 0.0480(4) Uani 1 1 d . . .
C14 C 0.2806(2) 0.11728(14) 0.51066(16) 0.0545(5) Uani 1 1 d . . .
H14A H 0.2669 0.1496 0.5822 0.065 Uiso 1 1 calc R . .
C15 C 0.18272(19) 0.05261(14) 0.44621(16) 0.0517(4) Uani 1 1 d . . .
H15A H 0.1040 0.0426 0.4753 0.062 Uiso 1 1 calc R . .
C16 C 0.19855(17) 0.00198(13) 0.33895(14) 0.0444(4) Uani 1 1 d . . .
C17 C 0.09035(15) -0.06712(14) 0.27534(15) 0.0444(4) Uani 1 1 d . . .
C18 C 0.02580(18) -0.14235(14) 0.32933(17) 0.0514(4) Uani 1 1 d . . .
H18A H 0.0441 -0.1581 0.4120 0.062 Uiso 1 1 calc R . .
C19 C -0.05113(16) -0.12324(13) 0.11230(16) 0.0476(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 C18 1.7219(19) . ?
S1 C19 1.7444(17) . ?
N1 C19 1.306(2) . ?
N1 C17 1.393(2) . ?
N2 C19 1.359(2) . ?
N2 H1N2 0.8528 . ?
N2 H2N2 0.9053 . ?
C1 C2 1.372(3) . ?
C1 C10 1.401(3) . ?
C1 H1A 0.9300 . ?
C2 C3 1.379(3) . ?
C2 H2A 0.9300 . ?
C3 C4 1.397(2) . ?
C3 H3A 0.9300 . ?
C4 C9 1.417(2) . ?
C4 C5 1.429(2) . ?
C5 C6 1.346(2) . ?
C5 H5A 0.9300 . ?
C6 C7 1.437(2) . ?
C6 H6A 0.9300 . ?
C7 C16 1.411(2) . ?
C7 C8 1.428(2) . ?
C8 C13 1.417(2) . ?
C8 C9 1.430(2) . ?
C9 C10 1.422(2) . ?
C10 C11 1.425(3) . ?
C11 C12 1.342(3) . ?
C11 H11A 0.9300 . ?
C12 C13 1.448(3) . ?
C12 H12A 0.9300 . ?
C13 C14 1.394(3) . ?
C14 C15 1.382(3) . ?
C14 H14A 0.9300 . ?
C15 C16 1.393(2) . ?
C15 H15A 0.9300 . ?
C16 C17 1.478(2) . ?
C17 C18 1.354(2) . ?
C18 H18A 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
C18 S1 C19 88.66(8) . . ?
C19 N1 C17 110.75(14) . . ?
C19 N2 H1N2 114.4 . . ?
C19 N2 H2N2 111.6 . . ?
H1N2 N2 H2N2 116.6 . . ?
C2 C1 C10 121.93(17) . . ?
C2 C1 H1A 119.0 . . ?
C10 C1 H1A 119.0 . . ?
C1 C2 C3 119.84(18) . . ?
C1 C2 H2A 120.1 . . ?
C3 C2 H2A 120.1 . . ?
C2 C3 C4 120.92(18) . . ?
C2 C3 H3A 119.5 . . ?
C4 C3 H3A 119.5 . . ?
C3 C4 C9 119.65(15) . . ?
C3 C4 C5 122.32(16) . . ?
C9 C4 C5 118.01(15) . . ?
C6 C5 C4 121.78(15) . . ?
C6 C5 H5A 119.1 . . ?
C4 C5 H5A 119.1 . . ?
C5 C6 C7 122.26(15) . . ?
C5 C6 H6A 118.9 . . ?
C7 C6 H6A 118.9 . . ?
C16 C7 C8 119.35(14) . . ?
C16 C7 C6 123.22(15) . . ?
C8 C7 C6 117.31(15) . . ?
C13 C8 C7 120.23(15) . . ?
C13 C8 C9 119.61(15) . . ?
C7 C8 C9 120.12(14) . . ?
C4 C9 C10 119.08(16) . . ?
C4 C9 C8 120.49(14) . . ?
C10 C9 C8 120.41(16) . . ?
C1 C10 C9 118.54(17) . . ?
C1 C10 C11 123.26(17) . . ?
C9 C10 C11 118.18(18) . . ?
C12 C11 C10 122.19(17) . . ?
C12 C11 H11A 118.9 . . ?
C10 C11 H11A 118.9 . . ?
C11 C12 C13 121.15(17) . . ?
C11 C12 H12A 119.4 . . ?
C13 C12 H12A 119.4 . . ?
C14 C13 C8 118.65(16) . . ?
C14 C13 C12 122.93(17) . . ?
C8 C13 C12 118.41(17) . . ?
C15 C14 C13 120.96(16) . . ?
C15 C14 H14A 119.5 . . ?
C13 C14 H14A 119.5 . . ?
C14 C15 C16 121.82(17) . . ?
C14 C15 H15A 119.1 . . ?
C16 C15 H15A 119.1 . . ?
C15 C16 C7 118.94(16) . . ?
C15 C16 C17 118.99(15) . . ?
C7 C16 C17 122.03(14) . . ?
C18 C17 N1 114.74(16) . . ?
C18 C17 C16 125.04(15) . . ?
N1 C17 C16 120.21(14) . . ?
C17 C18 S1 111.13(14) . . ?
C17 C18 H18A 124.4 . . ?
S1 C18 H18A 124.4 . . ?
N1 C19 N2 123.49(16) . . ?
N1 C19 S1 114.72(13) . . ?
N2 C19 S1 121.76(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
C10 C1 C2 C3 1.5(3) . . . . ?
C1 C2 C3 C4 0.0(3) . . . . ?
C2 C3 C4 C9 -0.9(2) . . . . ?
C2 C3 C4 C5 -179.45(16) . . . . ?
C3 C4 C5 C6 179.60(16) . . . . ?
C9 C4 C5 C6 1.0(2) . . . . ?
C4 C5 C6 C7 -1.1(3) . . . . ?
C5 C6 C7 C16 -176.45(16) . . . . ?
C5 C6 C7 C8 -0.4(2) . . . . ?
C16 C7 C8 C13 0.5(2) . . . . ?
C6 C7 C8 C13 -175.75(14) . . . . ?
C16 C7 C8 C9 178.10(13) . . . . ?
C6 C7 C8 C9 1.9(2) . . . . ?
C3 C4 C9 C10 0.3(2) . . . . ?
C5 C4 C9 C10 178.93(14) . . . . ?
C3 C4 C9 C8 -178.12(14) . . . . ?
C5 C4 C9 C8 0.5(2) . . . . ?
C13 C8 C9 C4 175.67(14) . . . . ?
C7 C8 C9 C4 -2.0(2) . . . . ?
C13 C8 C9 C10 -2.7(2) . . . . ?
C7 C8 C9 C10 179.65(13) . . . . ?
C2 C1 C10 C9 -2.0(3) . . . . ?
C2 C1 C10 C11 176.11(17) . . . . ?
C4 C9 C10 C1 1.1(2) . . . . ?
C8 C9 C10 C1 179.52(14) . . . . ?
C4 C9 C10 C11 -177.14(15) . . . . ?
C8 C9 C10 C11 1.3(2) . . . . ?
C1 C10 C11 C12 -177.64(17) . . . . ?
C9 C10 C11 C12 0.5(3) . . . . ?
C10 C11 C12 C13 -0.9(3) . . . . ?
C7 C8 C13 C14 1.4(2) . . . . ?
C9 C8 C13 C14 -176.19(14) . . . . ?
C7 C8 C13 C12 179.99(14) . . . . ?
C9 C8 C13 C12 2.4(2) . . . . ?
C11 C12 C13 C14 177.87(17) . . . . ?
C11 C12 C13 C8 -0.6(2) . . . . ?
C8 C13 C14 C15 -1.8(2) . . . . ?
C12 C13 C14 C15 179.67(16) . . . . ?
C13 C14 C15 C16 0.3(3) . . . . ?
C14 C15 C16 C7 1.7(2) . . . . ?
C14 C15 C16 C17 179.30(15) . . . . ?
C8 C7 C16 C15 -2.0(2) . . . . ?
C6 C7 C16 C15 173.98(15) . . . . ?
C8 C7 C16 C17 -179.57(14) . . . . ?
C6 C7 C16 C17 -3.6(2) . . . . ?
C19 N1 C17 C18 -0.1(2) . . . . ?
C19 N1 C17 C16 -179.04(14) . . . . ?
C15 C16 C17 C18 -46.7(2) . . . . ?
C7 C16 C17 C18 130.88(18) . . . . ?
C15 C16 C17 N1 132.18(16) . . . . ?
C7 C16 C17 N1 -50.3(2) . . . . ?
N1 C17 C18 S1 0.58(19) . . . . ?
C16 C17 C18 S1 179.49(13) . . . . ?
C19 S1 C18 C17 -0.68(13) . . . . ?
C17 N1 C19 N2 -178.47(16) . . . . ?
C17 N1 C19 S1 -0.48(18) . . . . ?
C18 S1 C19 N1 0.68(14) . . . . ?
C18 S1 C19 N2 178.71(16) . . . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        25.99
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.304
_refine_diff_density_min         -0.344
_refine_diff_density_rms         0.044

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag

N2 H2N2 N1 0.9100 2.1000 3.002(2) 174.00 3_555 yes
C6 H6A N1 0.9300 2.4900 3.068(2) 121.00 . yes



_database_code_depnum_ccdc_archive 'CCDC 1011198'
