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

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#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
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# 
#  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
#  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:
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#  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.
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data_NinSBz

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H13 N5 S'
_chemical_formula_sum            'C22 H13 N5 S'
_chemical_formula_weight         379.44

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'
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)/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                   9.9373(12)
_cell_length_b                   13.5639(16)
_cell_length_c                   13.7420(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.302(6)
_cell_angle_gamma                90.00
_cell_volume                     1809.7(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      4.14
_cell_measurement_theta_max      28.29

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.28
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.393
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             784
_exptl_absorpt_coefficient_mu    0.197
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.927
_exptl_absorpt_correction_T_max  0.946
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            25344
_diffrn_reflns_av_R_equivalents  0.0325
_diffrn_reflns_av_sigmaI/netI    0.0197
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         4.04
_diffrn_reflns_theta_max         28.38
_reflns_number_total             4521
_reflns_number_gt                3536
_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    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.1000P)²+0.6226P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    ?
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4491
_refine_ls_number_parameters     257
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0570
_refine_ls_R_factor_gt           0.0435
_refine_ls_wR_factor_ref         0.1517
_refine_ls_wR_factor_gt          0.1315
_refine_ls_goodness_of_fit_ref   0.920
_refine_ls_restrained_S_all      0.920
_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 0.62091(5) 0.40545(3) 1.21396(3) 0.04990(16) Uani 1 1 d . . .
C7 C 0.80992(16) 0.54297(11) 0.90736(12) 0.0397(3) Uani 1 1 d . . .
C8 C 0.91276(17) 0.60247(11) 0.87721(12) 0.0412(3) Uani 1 1 d . . .
C17 C 0.43835(17) 0.28413(11) 1.12004(12) 0.0417(3) Uani 1 1 d . . .
C15 C 0.82202(16) 0.55433(11) 1.01496(12) 0.0407(3) Uani 1 1 d . . .
C5 C 0.98872(17) 0.65462(12) 0.96661(12) 0.0433(3) Uani 1 1 d . . .
C16 C 0.58572(16) 0.39148(11) 1.08419(12) 0.0400(3) Uani 1 1 d . . .
C6 C 0.93333(16) 0.62535(12) 1.04856(12) 0.0422(3) Uani 1 1 d . . .
C9 C 0.8422(2) 0.54835(13) 0.71998(13) 0.0498(4) Uani 1 1 d . . .
C1 C 0.98657(18) 0.66356(14) 1.14297(13) 0.0487(4) Uani 1 1 d . . .
H1 H 0.9505 0.6447 1.1973 0.058 Uiso 1 1 calc R . .
C4 C 1.0968(2) 0.72091(14) 0.97899(15) 0.0526(4) Uani 1 1 d . . .
H4 H 1.1338 0.7401 0.9252 0.063 Uiso 1 1 calc R . .
C22 C 0.49640(17) 0.31560(12) 1.21682(13) 0.0439(3) Uani 1 1 d . . .
C14 C 0.73769(18) 0.49043(12) 0.74843(13) 0.0455(4) Uani 1 1 d . . .
C2 C 1.0946(2) 0.73029(15) 1.15433(14) 0.0555(4) Uani 1 1 d . . .
H2 H 1.1310 0.7566 1.2169 0.067 Uiso 1 1 calc R . .
C18 C 0.33516(19) 0.21316(13) 1.10498(15) 0.0527(4) Uani 1 1 d . . .
H18 H 0.2944 0.1923 1.0410 0.063 Uiso 1 1 calc R . .
C21 C 0.4550(2) 0.27583(15) 1.29931(14) 0.0572(5) Uani 1 1 d . . .
H21 H 0.4944 0.2968 1.3635 0.069 Uiso 1 1 calc R . .
C3 C 1.1488(2) 0.75814(15) 1.07373(16) 0.0577(5) Uani 1 1 d . . .
H3 H 1.2215 0.8027 1.0832 0.069 Uiso 1 1 calc R . .
C20 C 0.3539(2) 0.20440(16) 1.28293(16) 0.0624(5) Uani 1 1 d . . .
H20 H 0.3253 0.1763 1.3369 0.075 Uiso 1 1 calc R . .
C19 C 0.2943(2) 0.17410(15) 1.18729(17) 0.0608(5) Uani 1 1 d . . .
H19 H 0.2255 0.1265 1.1781 0.073 Uiso 1 1 calc R . .
C13 C 0.6483(2) 0.43424(15) 0.67668(16) 0.0595(5) Uani 1 1 d . . .
H13 H 0.5794 0.3967 0.6949 0.071 Uiso 1 1 calc R . .
C10 C 0.8541(3) 0.54705(16) 0.61971(15) 0.0661(6) Uani 1 1 d . . .
H10 H 0.9221 0.5842 0.5998 0.079 Uiso 1 1 calc R . .
C11 C 0.7652(3) 0.49099(18) 0.55121(16) 0.0756(7) Uani 1 1 d . . .
H11 H 0.7735 0.4906 0.4851 0.091 Uiso 1 1 calc R . .
C12 C 0.6627(3) 0.43470(18) 0.57993(17) 0.0724(6) Uani 1 1 d . . .
H12 H 0.6036 0.3971 0.5327 0.087 Uiso 1 1 calc R . .
N4 N 0.72237(14) 0.48736(10) 0.84585(11) 0.0440(3) Uani 1 1 d . . .
N2 N 0.65592(15) 0.44580(10) 1.02780(11) 0.0449(3) Uani 1 1 d . . .
N3 N 0.49132(15) 0.32781(11) 1.04369(11) 0.0466(3) Uani 1 1 d . . .
N1 N 0.75401(14) 0.50949(10) 1.07338(10) 0.0434(3) Uani 1 1 d . . .
N5 N 0.93226(17) 0.60611(11) 0.78653(11) 0.0500(4) Uani 1 1 d . . .
H51 H 0.6430(19) 0.4353(13) 0.9576(14) 0.038(4) Uiso 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 C22 1.7431(18) . ?
S1 C16 1.7529(17) . ?
C7 N4 1.314(2) . ?
C7 C8 1.431(2) . ?
C7 C15 1.466(2) . ?
C8 N5 1.302(2) . ?
C8 C5 1.478(2) . ?
C17 C18 1.389(2) . ?
C17 C22 1.399(2) . ?
C17 N3 1.402(2) . ?
C15 N1 1.305(2) . ?
C15 C6 1.465(2) . ?
C5 C4 1.383(2) . ?
C5 C6 1.412(2) . ?
C16 N3 1.309(2) . ?
C16 N2 1.364(2) . ?
C6 C1 1.393(2) . ?
C9 N5 1.379(2) . ?
C9 C10 1.408(3) . ?
C9 C14 1.422(3) . ?
C1 C2 1.387(3) . ?
C4 C3 1.389(3) . ?
C22 C21 1.394(2) . ?
C14 N4 1.380(2) . ?
C14 C13 1.403(3) . ?
C2 C3 1.383(3) . ?
C18 C19 1.386(3) . ?
C21 C20 1.380(3) . ?
C20 C19 1.384(3) . ?
C13 C12 1.367(3) . ?
C10 C11 1.375(3) . ?
C11 C12 1.395(4) . ?
N2 N1 1.352(2) . ?

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
C22 S1 C16 87.63(8) . . ?
N4 C7 C8 123.60(15) . . ?
N4 C7 C15 127.58(14) . . ?
C8 C7 C15 108.82(14) . . ?
N5 C8 C7 124.02(16) . . ?
N5 C8 C5 128.57(15) . . ?
C7 C8 C5 107.40(14) . . ?
C18 C17 C22 119.65(15) . . ?
C18 C17 N3 124.36(16) . . ?
C22 C17 N3 115.98(15) . . ?
N1 C15 C6 124.60(15) . . ?
N1 C15 C7 129.03(15) . . ?
C6 C15 C7 106.33(13) . . ?
C4 C5 C6 120.62(16) . . ?
C4 C5 C8 131.22(16) . . ?
C6 C5 C8 108.16(15) . . ?
N3 C16 N2 121.46(15) . . ?
N3 C16 S1 118.26(12) . . ?
N2 C16 S1 120.28(13) . . ?
C1 C6 C5 120.21(16) . . ?
C1 C6 C15 130.52(16) . . ?
C5 C6 C15 109.27(14) . . ?
N5 C9 C10 118.58(18) . . ?
N5 C9 C14 122.70(16) . . ?
C10 C9 C14 118.72(18) . . ?
C2 C1 C6 118.62(17) . . ?
C5 C4 C3 118.38(17) . . ?
C21 C22 C17 121.44(17) . . ?
C21 C22 S1 128.51(15) . . ?
C17 C22 S1 110.05(12) . . ?
N4 C14 C13 118.77(17) . . ?
N4 C14 C9 121.43(16) . . ?
C13 C14 C9 119.80(17) . . ?
C3 C2 C1 120.79(17) . . ?
C19 C18 C17 118.58(18) . . ?
C20 C21 C22 118.03(19) . . ?
C2 C3 C4 121.38(18) . . ?
C21 C20 C19 120.84(17) . . ?
C20 C19 C18 121.43(18) . . ?
C12 C13 C14 119.9(2) . . ?
C11 C10 C9 120.1(2) . . ?
C10 C11 C12 120.7(2) . . ?
C13 C12 C11 120.8(2) . . ?
C7 N4 C14 114.32(14) . . ?
N1 N2 C16 119.17(14) . . ?
C16 N3 C17 108.07(14) . . ?
C15 N1 N2 115.44(14) . . ?
C8 N5 C9 113.90(15) . . ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        28.38
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.512
_refine_diff_density_min         -0.340
_refine_diff_density_rms         0.043
_database_code_depnum_ccdc_archive 'CCDC 1000228'
