# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mo_20141114c_0m
_database_code_depnum_ccdc_archive 'CCDC 1034468'
_audit_update_record             
;
2014-11-15 deposited with the CCDC.
2015-04-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H15 N3 S'
_chemical_formula_sum            'C22 H15 N3 S'
_chemical_formula_weight         353.43

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           Orthorhombic
_symmetry_space_group_name_H-M   'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'

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

_cell_length_a                   8.4993(5)
_cell_length_b                   17.7777(11)
_cell_length_c                   23.0409(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3481.4(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    4353
_cell_measurement_theta_min      2.79
_cell_measurement_theta_max      26.79

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1472
_exptl_absorpt_coefficient_mu    0.196
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9472
_exptl_absorpt_correction_T_max  0.9600
_exptl_absorpt_process_details   'SADABS (Bruker, 2002)'

_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  'Bruker APEX II area-detector diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            15000
_diffrn_reflns_av_R_equivalents  0.0281
_diffrn_reflns_av_sigmaI/netI    0.0256
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         2.46
_diffrn_reflns_theta_max         26.00
_reflns_number_total             3408
_reflns_number_gt                2655
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'SMART (Bruker, 2002)'
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'XP (Bruker, 2002)'
_computing_publication_material  'SHELXL-97 (Bruker, 2002)'

_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)+(0.0900P)²+0.2715P] 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         3408
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0574
_refine_ls_R_factor_gt           0.0403
_refine_ls_wR_factor_ref         0.1425
_refine_ls_wR_factor_gt          0.1268
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_restrained_S_all      1.097
_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 0.04563(6) 0.09641(3) 0.59000(2) 0.0501(2) Uani 1 1 d . . .
N1 N 0.10399(17) 0.27140(8) 0.62531(6) 0.0408(4) Uani 1 1 d . . .
N2 N 0.31398(19) 0.18675(9) 0.62599(7) 0.0490(4) Uani 1 1 d . . .
N3 N 0.3038(2) 0.28620(9) 0.55684(7) 0.0508(4) Uani 1 1 d . . .
C1 C 0.0895(2) 0.34531(10) 0.64797(8) 0.0419(4) Uani 1 1 d . . .
C2 C 0.1724(3) 0.41003(10) 0.63400(10) 0.0519(5) Uani 1 1 d . . .
H2 H 0.2496 0.4098 0.6054 0.062 Uiso 1 1 calc R . .
C3 C 0.1358(3) 0.47483(11) 0.66425(11) 0.0607(6) Uani 1 1 d . . .
H3 H 0.1898 0.5190 0.6559 0.073 Uiso 1 1 calc R . .
C4 C 0.0201(3) 0.47545(11) 0.70698(11) 0.0636(6) Uani 1 1 d . . .
H4 H -0.0018 0.5199 0.7267 0.076 Uiso 1 1 calc R . .
C5 C -0.0621(3) 0.41165(11) 0.72039(10) 0.0571(6) Uani 1 1 d . . .
H5 H -0.1401 0.4125 0.7487 0.068 Uiso 1 1 calc R . .
C6 C -0.0267(2) 0.34533(10) 0.69091(8) 0.0441(4) Uani 1 1 d . . .
C7 C -0.0883(2) 0.26982(10) 0.69478(8) 0.0423(4) Uani 1 1 d . . .
C8 C -0.0057(2) 0.22538(10) 0.65481(7) 0.0376(4) Uani 1 1 d . . .
C9 C -0.0473(2) 0.15007(10) 0.64527(8) 0.0396(4) Uani 1 1 d . . .
C10 C -0.1666(2) 0.12119(11) 0.68045(8) 0.0496(5) Uani 1 1 d . . .
H10 H -0.1952 0.0710 0.6763 0.060 Uiso 1 1 calc R . .
C11 C -0.2435(3) 0.16452(12) 0.72112(9) 0.0600(6) Uani 1 1 d . . .
H11 H -0.3213 0.1428 0.7440 0.072 Uiso 1 1 calc R . .
C12 C -0.2076(2) 0.23909(12) 0.72845(9) 0.0553(5) Uani 1 1 d . . .
H12 H -0.2618 0.2684 0.7553 0.066 Uiso 1 1 calc R . .
C13 C 0.2483(2) 0.24615(10) 0.60113(7) 0.0395(4) Uani 1 1 d . . .
C14 C 0.4532(2) 0.16636(13) 0.60405(11) 0.0583(6) Uani 1 1 d . . .
H14 H 0.5035 0.1245 0.6196 0.070 Uiso 1 1 calc R . .
C15 C 0.5248(3) 0.20417(12) 0.55986(11) 0.0634(6) Uani 1 1 d . . .
H15 H 0.6230 0.1899 0.5458 0.076 Uiso 1 1 calc R . .
C16 C 0.4450(3) 0.26401(12) 0.53729(10) 0.0603(6) Uani 1 1 d . . .
H16 H 0.4907 0.2907 0.5069 0.072 Uiso 1 1 calc R . .
C17 C -0.0934(2) 0.02435(11) 0.57598(9) 0.0470(5) Uani 1 1 d . . .
C18 C -0.1959(3) 0.03110(14) 0.52977(10) 0.0638(6) Uani 1 1 d . . .
H18 H -0.1970 0.0748 0.5076 0.077 Uiso 1 1 calc R . .
C19 C -0.2961(3) -0.0269(2) 0.51662(14) 0.0932(10) Uani 1 1 d . . .
H19 H -0.3644 -0.0225 0.4853 0.112 Uiso 1 1 calc R . .
C20 C -0.2964(4) -0.0904(2) 0.54878(19) 0.1084(14) Uani 1 1 d . . .
H20 H -0.3664 -0.1289 0.5398 0.130 Uiso 1 1 calc R . .
C21 C -0.1950(4) -0.09868(14) 0.59430(17) 0.0949(12) Uani 1 1 d . . .
H21 H -0.1954 -0.1429 0.6159 0.114 Uiso 1 1 calc R . .
C22 C -0.0907(3) -0.04083(12) 0.60843(12) 0.0637(6) Uani 1 1 d . . .
H22 H -0.0207 -0.0461 0.6392 0.076 Uiso 1 1 calc R . .


_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 C17 1.772(2) . ?
S1 C9 1.7765(18) . ?
N1 C8 1.414(2) . ?
N1 C1 1.419(2) . ?
N1 C13 1.420(2) . ?
N2 C13 1.325(2) . ?
N2 C14 1.337(3) . ?
N3 C13 1.331(2) . ?
N3 C16 1.341(3) . ?
C1 C2 1.387(3) . ?
C1 C6 1.398(3) . ?
C2 C3 1.382(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.392(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.367(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.394(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.443(3) . ?
C7 C12 1.389(3) . ?
C7 C8 1.402(2) . ?
C8 C9 1.402(2) . ?
C9 C10 1.396(3) . ?
C10 C11 1.378(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.371(3) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C14 C15 1.364(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.365(3) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 C22 1.379(3) . ?
C17 C18 1.381(3) . ?
C18 C19 1.372(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.350(5) . ?
C19 H19 0.9300 . ?
C20 C21 1.365(5) . ?
C20 H20 0.9300 . ?
C21 C22 1.396(4) . ?
C21 H21 0.9300 . ?
C22 H22 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
C17 S1 C9 102.84(9) . . ?
C8 N1 C1 107.55(14) . . ?
C8 N1 C13 125.09(14) . . ?
C1 N1 C13 120.79(14) . . ?
C13 N2 C14 115.20(18) . . ?
C13 N3 C16 114.67(17) . . ?
C2 C1 C6 121.52(18) . . ?
C2 C1 N1 129.70(18) . . ?
C6 C1 N1 108.77(16) . . ?
C3 C2 C1 117.4(2) . . ?
C3 C2 H2 121.3 . . ?
C1 C2 H2 121.3 . . ?
C2 C3 C4 121.5(2) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
C5 C4 C3 121.0(2) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
C4 C5 C6 118.8(2) . . ?
C4 C5 H5 120.6 . . ?
C6 C5 H5 120.6 . . ?
C5 C6 C1 119.85(18) . . ?
C5 C6 C7 132.73(19) . . ?
C1 C6 C7 107.43(16) . . ?
C12 C7 C8 120.72(17) . . ?
C12 C7 C6 131.68(18) . . ?
C8 C7 C6 107.59(16) . . ?
C7 C8 C9 120.99(17) . . ?
C7 C8 N1 108.65(15) . . ?
C9 C8 N1 130.04(16) . . ?
C10 C9 C8 116.33(16) . . ?
C10 C9 S1 122.80(14) . . ?
C8 C9 S1 120.85(13) . . ?
C11 C10 C9 122.27(18) . . ?
C11 C10 H10 118.9 . . ?
C9 C10 H10 118.9 . . ?
C12 C11 C10 121.25(19) . . ?
C12 C11 H11 119.4 . . ?
C10 C11 H11 119.4 . . ?
C11 C12 C7 118.31(18) . . ?
C11 C12 H12 120.8 . . ?
C7 C12 H12 120.8 . . ?
N2 C13 N3 127.48(17) . . ?
N2 C13 N1 116.53(15) . . ?
N3 C13 N1 115.97(16) . . ?
N2 C14 C15 123.0(2) . . ?
N2 C14 H14 118.5 . . ?
C15 C14 H14 118.5 . . ?
C14 C15 C16 116.5(2) . . ?
C14 C15 H15 121.7 . . ?
C16 C15 H15 121.7 . . ?
N3 C16 C15 123.1(2) . . ?
N3 C16 H16 118.4 . . ?
C15 C16 H16 118.4 . . ?
C22 C17 C18 120.1(2) . . ?
C22 C17 S1 119.82(18) . . ?
C18 C17 S1 119.89(17) . . ?
C19 C18 C17 119.8(3) . . ?
C19 C18 H18 120.1 . . ?
C17 C18 H18 120.1 . . ?
C20 C19 C18 120.6(3) . . ?
C20 C19 H19 119.7 . . ?
C18 C19 H19 119.7 . . ?
C19 C20 C21 120.7(3) . . ?
C19 C20 H20 119.6 . . ?
C21 C20 H20 119.6 . . ?
C20 C21 C22 120.0(3) . . ?
C20 C21 H21 120.0 . . ?
C22 C21 H21 120.0 . . ?
C17 C22 C21 118.8(3) . . ?
C17 C22 H22 120.6 . . ?
C21 C22 H22 120.6 . . ?

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
C8 N1 C1 C2 178.90(19) . . . . ?
C13 N1 C1 C2 26.0(3) . . . . ?
C8 N1 C1 C6 0.1(2) . . . . ?
C13 N1 C1 C6 -152.79(16) . . . . ?
C6 C1 C2 C3 0.1(3) . . . . ?
N1 C1 C2 C3 -178.54(19) . . . . ?
C1 C2 C3 C4 -0.2(3) . . . . ?
C2 C3 C4 C5 -0.2(4) . . . . ?
C3 C4 C5 C6 0.7(3) . . . . ?
C4 C5 C6 C1 -0.8(3) . . . . ?
C4 C5 C6 C7 179.3(2) . . . . ?
C2 C1 C6 C5 0.5(3) . . . . ?
N1 C1 C6 C5 179.34(17) . . . . ?
C2 C1 C6 C7 -179.64(18) . . . . ?
N1 C1 C6 C7 -0.8(2) . . . . ?
C5 C6 C7 C12 2.3(4) . . . . ?
C1 C6 C7 C12 -177.6(2) . . . . ?
C5 C6 C7 C8 -179.0(2) . . . . ?
C1 C6 C7 C8 1.1(2) . . . . ?
C12 C7 C8 C9 3.8(3) . . . . ?
C6 C7 C8 C9 -175.08(16) . . . . ?
C12 C7 C8 N1 177.85(17) . . . . ?
C6 C7 C8 N1 -1.0(2) . . . . ?
C1 N1 C8 C7 0.56(19) . . . . ?
C13 N1 C8 C7 152.01(16) . . . . ?
C1 N1 C8 C9 173.90(18) . . . . ?
C13 N1 C8 C9 -34.6(3) . . . . ?
C7 C8 C9 C10 -4.4(3) . . . . ?
N1 C8 C9 C10 -177.00(18) . . . . ?
C7 C8 C9 S1 174.25(14) . . . . ?
N1 C8 C9 S1 1.6(3) . . . . ?
C17 S1 C9 C10 21.08(19) . . . . ?
C17 S1 C9 C8 -157.43(15) . . . . ?
C8 C9 C10 C11 2.1(3) . . . . ?
S1 C9 C10 C11 -176.51(17) . . . . ?
C9 C10 C11 C12 0.9(4) . . . . ?
C10 C11 C12 C7 -1.6(3) . . . . ?
C8 C7 C12 C11 -0.7(3) . . . . ?
C6 C7 C12 C11 177.9(2) . . . . ?
C14 N2 C13 N3 1.2(3) . . . . ?
C14 N2 C13 N1 -177.04(17) . . . . ?
C16 N3 C13 N2 -2.3(3) . . . . ?
C16 N3 C13 N1 175.92(17) . . . . ?
C8 N1 C13 N2 -27.8(2) . . . . ?
C1 N1 C13 N2 120.20(18) . . . . ?
C8 N1 C13 N3 153.79(17) . . . . ?
C1 N1 C13 N3 -58.2(2) . . . . ?
C13 N2 C14 C15 1.0(3) . . . . ?
N2 C14 C15 C16 -1.7(4) . . . . ?
C13 N3 C16 C15 1.4(3) . . . . ?
C14 C15 C16 N3 0.4(4) . . . . ?
C9 S1 C17 C22 -87.25(17) . . . . ?
C9 S1 C17 C18 97.81(17) . . . . ?
C22 C17 C18 C19 0.7(3) . . . . ?
S1 C17 C18 C19 175.58(18) . . . . ?
C17 C18 C19 C20 0.6(4) . . . . ?
C18 C19 C20 C21 -1.3(4) . . . . ?
C19 C20 C21 C22 0.7(4) . . . . ?
C18 C17 C22 C21 -1.2(3) . . . . ?
S1 C17 C22 C21 -176.11(17) . . . . ?
C20 C21 C22 C17 0.5(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.275
_refine_diff_density_min         -0.384
_refine_diff_density_rms         0.099
