# 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_shelxl
#TrackingRef 'adsm41.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H14 N4 O2 S'
_chemical_formula_sum            'C15 H14 N4 O2 S'
_chemical_formula_weight         314.37

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'
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   P21/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                   11.9823(6)
_cell_length_b                   8.3551(4)
_cell_length_c                   17.5510(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.948(2)
_cell_angle_gamma                90.00
_cell_volume                     1697.63(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9861
_cell_measurement_theta_min      4.804
_cell_measurement_theta_max      56.405

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.230
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             656
_exptl_absorpt_coefficient_mu    0.202
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9058
_exptl_absorpt_correction_T_max  0.9419
_exptl_absorpt_process_details   'SADABS (Bruker, 1999)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      296(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 axs kappa apex2 CCD Diffractometer'
_diffrn_measurement_method       '\w and \f scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            24860
_diffrn_reflns_av_R_equivalents  0.0211
_diffrn_reflns_av_sigmaI/netI    0.0114
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.76
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2982
_reflns_number_gt                2763
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_structure_solution    'SIR92 (Altornare et al., 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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^)+(0.1810P)^2^+1.2822P] 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    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.042(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         2982
_refine_ls_number_parameters     206
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0769
_refine_ls_R_factor_gt           0.0735
_refine_ls_wR_factor_ref         0.2592
_refine_ls_wR_factor_gt          0.2496
_refine_ls_goodness_of_fit_ref   1.153
_refine_ls_restrained_S_all      1.153
_refine_ls_shift/su_max          0.004
_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
C1 C 0.1786(3) 0.2946(4) 0.1881(2) 0.0485(9) Uani 1 1 d . . .
H1 H 0.1967 0.3339 0.1432 0.058 Uiso 1 1 calc R . .
C2 C 0.1365(4) 0.3962(5) 0.2376(3) 0.0634(12) Uani 1 1 d . . .
H2 H 0.1268 0.5046 0.2257 0.076 Uiso 1 1 calc R . .
C3 C 0.1090(4) 0.3363(5) 0.3046(3) 0.0670(12) Uani 1 1 d . . .
H3 H 0.0812 0.4056 0.3369 0.080 Uiso 1 1 calc R . .
C4 C 0.1224(4) 0.1757(5) 0.3240(2) 0.0564(10) Uani 1 1 d . . .
H4 H 0.1036 0.1355 0.3685 0.068 Uiso 1 1 calc R . .
C5 C 0.1648(3) 0.0771(4) 0.27457(19) 0.0390(8) Uani 1 1 d . . .
C6 C 0.1927(2) 0.1348(4) 0.20766(17) 0.0337(7) Uani 1 1 d . . .
C7 C 0.2375(2) -0.0022(4) 0.16781(16) 0.0287(7) Uani 1 1 d . . .
C8 C 0.2367(2) -0.1414(4) 0.22603(16) 0.0309(7) Uani 1 1 d . . .
C9 C 0.3538(2) 0.0195(4) 0.15179(16) 0.0302(7) Uani 1 1 d . . .
C10 C 0.4506(3) 0.0709(4) 0.20811(18) 0.0389(8) Uani 1 1 d . . .
C11 C 0.4670(3) 0.1171(6) 0.2925(2) 0.0610(12) Uani 1 1 d . . .
H11A H 0.5461 0.1470 0.3147 0.091 Uiso 1 1 calc R . .
H11B H 0.4479 0.0281 0.3213 0.091 Uiso 1 1 calc R . .
H11C H 0.4177 0.2060 0.2958 0.091 Uiso 1 1 calc R . .
C12 C 0.3948(3) -0.0110(4) 0.08446(17) 0.0348(7) Uani 1 1 d . . .
C13 C 0.2482(3) -0.1555(4) -0.01949(17) 0.0381(7) Uani 1 1 d . . .
C14 C 0.1852(3) -0.2138(4) 0.03913(18) 0.0371(7) Uani 1 1 d . . .
H14 H 0.2414 -0.2652 0.0828 0.045 Uiso 1 1 calc R . .
C15 C 0.0915(4) -0.3367(5) 0.0033(3) 0.0633(12) Uani 1 1 d . . .
H15A H 0.0539 -0.3707 0.0427 0.095 Uiso 1 1 calc R . .
H15B H 0.1261 -0.4274 -0.0152 0.095 Uiso 1 1 calc R . .
H15C H 0.0357 -0.2889 -0.0400 0.095 Uiso 1 1 calc R . .
N1 N 0.1903(2) -0.0869(3) 0.28319(16) 0.0413(7) Uani 1 1 d . . .
H1N1 H 0.1778 -0.1454 0.3204 0.050 Uiso 1 1 calc R . .
N2 N 0.5070(2) 0.0211(4) 0.09846(16) 0.0450(8) Uani 1 1 d . . .
N3 N 0.3407(3) -0.0594(4) 0.00780(16) 0.0442(8) Uani 1 1 d . . .
H3A H 0.3710 -0.0220 -0.0279 0.053 Uiso 1 1 calc R . .
N4 N 0.5384(3) 0.0704(4) 0.17362(17) 0.0451(8) Uani 1 1 d . . .
O1 O 0.2184(2) -0.1920(4) -0.08934(14) 0.0563(8) Uani 1 1 d . . .
O2 O 0.27380(19) -0.2770(3) 0.22073(13) 0.0407(6) Uani 1 1 d . . .
S1 S 0.12277(6) -0.04419(10) 0.07855(4) 0.0356(4) Uani 1 1 d . . .
H4N4 H 0.596(3) 0.110(4) 0.186(2) 0.035(9) Uiso 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 0.0493(19) 0.0404(18) 0.061(2) 0.0019(15) 0.0231(17) -0.0031(14)
C2 0.058(2) 0.0399(19) 0.099(3) -0.013(2) 0.031(2) -0.0019(17)
C3 0.062(2) 0.064(3) 0.086(3) -0.028(2) 0.040(2) -0.004(2)
C4 0.061(2) 0.069(2) 0.049(2) -0.0123(18) 0.0318(18) -0.0025(19)
C5 0.0351(16) 0.0471(18) 0.0382(17) -0.0028(13) 0.0159(13) -0.0029(13)
C6 0.0294(14) 0.0396(16) 0.0338(15) -0.0022(12) 0.0113(12) -0.0030(11)
C7 0.0260(14) 0.0355(15) 0.0250(14) 0.0020(11) 0.0074(11) -0.0030(11)
C8 0.0246(13) 0.0399(16) 0.0281(14) 0.0053(11) 0.0062(11) -0.0017(11)
C9 0.0295(14) 0.0389(15) 0.0240(14) -0.0007(11) 0.0103(11) -0.0063(11)
C10 0.0338(16) 0.0547(19) 0.0291(16) -0.0047(13) 0.0096(13) -0.0124(13)
C11 0.046(2) 0.108(3) 0.0310(17) -0.0179(19) 0.0128(15) -0.026(2)
C12 0.0341(16) 0.0461(16) 0.0279(15) -0.0055(13) 0.0145(12) -0.0111(13)
C13 0.0406(16) 0.0446(17) 0.0295(15) -0.0070(13) 0.0096(12) -0.0050(13)
C14 0.0350(15) 0.0418(17) 0.0338(16) -0.0056(12) 0.0076(12) -0.0096(13)
C15 0.062(2) 0.063(2) 0.067(3) -0.023(2) 0.021(2) -0.032(2)
N1 0.0455(16) 0.0504(16) 0.0342(14) 0.0109(12) 0.0217(12) 0.0021(12)
N2 0.0366(15) 0.0691(19) 0.0338(15) -0.0121(13) 0.0172(12) -0.0201(13)
N3 0.0424(16) 0.0670(19) 0.0279(14) -0.0106(12) 0.0173(12) -0.0198(13)
N4 0.0304(15) 0.073(2) 0.0342(15) -0.0115(13) 0.0117(12) -0.0219(14)
O1 0.0663(17) 0.0701(18) 0.0325(13) -0.0188(11) 0.0126(11) -0.0192(13)
O2 0.0392(12) 0.0425(13) 0.0414(13) 0.0099(9) 0.0120(10) 0.0064(9)
S1 0.0271(5) 0.0489(6) 0.0290(6) 0.0007(3) 0.0039(4) -0.0003(3)

_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 C6 1.378(5) . ?
C1 C2 1.398(5) . ?
C2 C3 1.394(7) . ?
C3 C4 1.383(6) . ?
C4 C5 1.385(5) . ?
C5 C6 1.387(4) . ?
C5 N1 1.404(4) . ?
C6 C7 1.511(4) . ?
C7 C9 1.503(4) . ?
C7 C8 1.550(4) . ?
C7 S1 1.832(3) . ?
C8 O2 1.229(4) . ?
C8 N1 1.346(4) . ?
C9 C10 1.384(4) . ?
C9 C12 1.415(4) . ?
C10 N4 1.342(4) . ?
C10 C11 1.494(4) . ?
C12 N2 1.330(4) . ?
C12 N3 1.395(4) . ?
C13 O1 1.224(4) . ?
C13 N3 1.352(4) . ?
C13 C14 1.506(4) . ?
C14 C15 1.531(4) . ?
C14 S1 1.820(3) . ?
N2 N4 1.340(4) . ?

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
C6 C1 C2 118.3(3) . . ?
C3 C2 C1 120.5(4) . . ?
C4 C3 C2 121.2(4) . . ?
C3 C4 C5 117.4(4) . . ?
C4 C5 C6 122.1(3) . . ?
C4 C5 N1 128.2(3) . . ?
C6 C5 N1 109.7(3) . . ?
C1 C6 C5 120.4(3) . . ?
C1 C6 C7 130.9(3) . . ?
C5 C6 C7 108.7(3) . . ?
C9 C7 C6 116.9(2) . . ?
C9 C7 C8 112.2(2) . . ?
C6 C7 C8 101.6(2) . . ?
C9 C7 S1 113.00(19) . . ?
C6 C7 S1 105.26(19) . . ?
C8 C7 S1 106.85(19) . . ?
O2 C8 N1 126.5(3) . . ?
O2 C8 C7 125.3(3) . . ?
N1 C8 C7 108.1(2) . . ?
C10 C9 C12 104.1(3) . . ?
C10 C9 C7 123.4(3) . . ?
C12 C9 C7 132.3(3) . . ?
N4 C10 C9 106.7(3) . . ?
N4 C10 C11 122.0(3) . . ?
C9 C10 C11 131.3(3) . . ?
N2 C12 N3 115.7(3) . . ?
N2 C12 C9 111.2(3) . . ?
N3 C12 C9 133.0(3) . . ?
O1 C13 N3 120.2(3) . . ?
O1 C13 C14 122.4(3) . . ?
N3 C13 C14 117.4(3) . . ?
C13 C14 C15 112.4(3) . . ?
C13 C14 S1 109.6(2) . . ?
C15 C14 S1 110.4(3) . . ?
C8 N1 C5 111.7(3) . . ?
C12 N2 N4 104.9(2) . . ?
C13 N3 C12 130.5(3) . . ?
N2 N4 C10 113.0(3) . . ?
C14 S1 C7 100.54(14) . . ?

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
C6 C1 C2 C3 -0.4(6) . . . . ?
C1 C2 C3 C4 -0.1(7) . . . . ?
C2 C3 C4 C5 0.4(7) . . . . ?
C3 C4 C5 C6 -0.4(6) . . . . ?
C3 C4 C5 N1 177.1(4) . . . . ?
C2 C1 C6 C5 0.4(5) . . . . ?
C2 C1 C6 C7 -178.8(3) . . . . ?
C4 C5 C6 C1 0.0(5) . . . . ?
N1 C5 C6 C1 -177.9(3) . . . . ?
C4 C5 C6 C7 179.3(3) . . . . ?
N1 C5 C6 C7 1.4(4) . . . . ?
C1 C6 C7 C9 53.6(4) . . . . ?
C5 C6 C7 C9 -125.7(3) . . . . ?
C1 C6 C7 C8 176.0(3) . . . . ?
C5 C6 C7 C8 -3.3(3) . . . . ?
C1 C6 C7 S1 -72.8(4) . . . . ?
C5 C6 C7 S1 108.0(2) . . . . ?
C9 C7 C8 O2 -49.4(4) . . . . ?
C6 C7 C8 O2 -175.0(3) . . . . ?
S1 C7 C8 O2 75.0(3) . . . . ?
C9 C7 C8 N1 129.8(3) . . . . ?
C6 C7 C8 N1 4.1(3) . . . . ?
S1 C7 C8 N1 -105.9(2) . . . . ?
C6 C7 C9 C10 49.6(4) . . . . ?
C8 C7 C9 C10 -67.1(4) . . . . ?
S1 C7 C9 C10 172.0(3) . . . . ?
C6 C7 C9 C12 -134.3(3) . . . . ?
C8 C7 C9 C12 109.0(4) . . . . ?
S1 C7 C9 C12 -11.8(4) . . . . ?
C12 C9 C10 N4 0.7(4) . . . . ?
C7 C9 C10 N4 177.8(3) . . . . ?
C12 C9 C10 C11 -177.8(4) . . . . ?
C7 C9 C10 C11 -0.7(6) . . . . ?
C10 C9 C12 N2 -0.7(4) . . . . ?
C7 C9 C12 N2 -177.4(3) . . . . ?
C10 C9 C12 N3 -177.2(4) . . . . ?
C7 C9 C12 N3 6.1(6) . . . . ?
O1 C13 C14 C15 6.8(5) . . . . ?
N3 C13 C14 C15 -173.3(3) . . . . ?
O1 C13 C14 S1 -116.3(3) . . . . ?
N3 C13 C14 S1 63.6(3) . . . . ?
O2 C8 N1 C5 175.5(3) . . . . ?
C7 C8 N1 C5 -3.6(3) . . . . ?
C4 C5 N1 C8 -176.3(3) . . . . ?
C6 C5 N1 C8 1.5(4) . . . . ?
N3 C12 N2 N4 177.6(3) . . . . ?
C9 C12 N2 N4 0.4(4) . . . . ?
O1 C13 N3 C12 -175.1(4) . . . . ?
C14 C13 N3 C12 5.0(5) . . . . ?
N2 C12 N3 C13 151.2(4) . . . . ?
C9 C12 N3 C13 -32.5(6) . . . . ?
C12 N2 N4 C10 0.0(4) . . . . ?
C9 C10 N4 N2 -0.5(4) . . . . ?
C11 C10 N4 N2 178.2(4) . . . . ?
C13 C14 S1 C7 -93.9(2) . . . . ?
C15 C14 S1 C7 141.8(3) . . . . ?
C9 C7 S1 C14 53.4(2) . . . . ?
C6 C7 S1 C14 -177.94(19) . . . . ?
C8 C7 S1 C14 -70.5(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         2.037
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.185


_database_code_depnum_ccdc_archive 'CCDC 912381'