# 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 
# 
#######################################################################
# 
#  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
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#  data retrieval see:
#                         www.ccdc.cam.ac.uk
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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_sb107s

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C5 H10 N4 O S, C8 H6 N2, H2 O'
_chemical_formula_sum            'C13 H18 N6 O2 S'
_chemical_formula_weight         322.39

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           Triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_symmetry_Int_Tables_number      2

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.345(3)
_cell_length_b                   8.053(3)
_cell_length_c                   14.531(5)
_cell_angle_alpha                91.821(6)
_cell_angle_beta                 100.056(6)
_cell_angle_gamma                115.273(5)
_cell_volume                     759.8(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3635
_cell_measurement_theta_min      1.43
_cell_measurement_theta_max      28.36

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             340
_exptl_absorpt_coefficient_mu    0.230
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.973
_exptl_absorpt_correction_T_max  0.982
_exptl_absorpt_process_details   'Sadabs(Sheldrick, 1996)'

_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9166
_diffrn_reflns_av_R_equivalents  0.0557
_diffrn_reflns_av_sigmaI/netI    0.0762
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.43
_diffrn_reflns_theta_max         28.36
_reflns_number_total             3635
_reflns_number_gt                2468
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0799P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    noref
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3635
_refine_ls_number_parameters     201
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0791
_refine_ls_R_factor_gt           0.0609
_refine_ls_wR_factor_ref         0.1548
_refine_ls_wR_factor_gt          0.1461
_refine_ls_goodness_of_fit_ref   0.951
_refine_ls_restrained_S_all      0.951
_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 0.48498(10) 0.89732(9) 1.13008(4) 0.0305(2) Uani 1 1 d . . .
O1 O -0.1704(3) 0.2102(2) 0.61602(11) 0.0288(4) Uani 1 1 d . . .
H1 H -0.2179 0.2293 0.5626 0.043 Uiso 1 1 d R . .
N1 N 0.3563(3) 0.5355(3) 1.08680(13) 0.0263(5) Uani 1 1 d . . .
H1A H 0.2906 0.4327 1.0476 0.032 Uiso 1 1 d R . .
H1B H 0.4178 0.5337 1.1442 0.032 Uiso 1 1 d R . .
N2 N 0.2656(3) 0.6881(3) 0.97027(13) 0.0240(5) Uani 1 1 d . . .
H2 H 0.2591 0.7884 0.9512 0.029 Uiso 1 1 d R . .
N3 N 0.1768(3) 0.5260(3) 0.90947(13) 0.0225(4) Uani 1 1 d . . .
N4 N -0.0974(3) 0.3704(3) 0.67956(14) 0.0248(5) Uani 1 1 d . . .
C1 C 0.3628(3) 0.6926(3) 1.05918(16) 0.0226(5) Uani 1 1 d . . .
C2 C 0.0712(3) 0.5277(3) 0.82830(16) 0.0216(5) Uani 1 1 d . . .
C3 C -0.0108(3) 0.3563(3) 0.76198(16) 0.0229(5) Uani 1 1 d . . .
C4 C 0.0313(4) 0.6891(3) 0.79890(17) 0.0246(5) Uani 1 1 d . . .
H4A H 0.0159 0.7527 0.8535 0.037 Uiso 1 1 calc R . .
H4B H -0.0951 0.6442 0.7503 0.037 Uiso 1 1 calc R . .
H4C H 0.1473 0.7753 0.7738 0.037 Uiso 1 1 calc R . .
C5 C 0.0167(4) 0.1907(3) 0.79113(17) 0.0298(6) Uani 1 1 d . . .
H5A H -0.0798 0.0816 0.7469 0.045 Uiso 1 1 calc R . .
H5B H -0.0100 0.1709 0.8546 0.045 Uiso 1 1 calc R . .
H5C H 0.1581 0.2110 0.7910 0.045 Uiso 1 1 calc R . .
N5 N 0.6829(3) 0.3275(3) 0.43886(14) 0.0255(5) Uani 1 1 d . . .
N6 N 0.5165(3) 0.4565(3) 0.28089(13) 0.0230(5) Uani 1 1 d . . .
C6 C 0.6998(3) 0.5046(3) 0.44382(16) 0.0214(5) Uani 1 1 d . . .
C7 C 0.7995(4) 0.6246(3) 0.52879(16) 0.0247(5) Uani 1 1 d . . .
H7 H 0.8593 0.5843 0.5814 0.030 Uiso 1 1 calc R . .
C8 C 0.8102(4) 0.7982(3) 0.53536(17) 0.0264(6) Uani 1 1 d . . .
H8 H 0.8776 0.8782 0.5926 0.032 Uiso 1 1 calc R . .
C9 C 0.7215(4) 0.8599(3) 0.45746(17) 0.0275(6) Uani 1 1 d . . .
H9 H 0.7278 0.9801 0.4633 0.033 Uiso 1 1 calc R . .
C10 C 0.6266(4) 0.7475(3) 0.37355(17) 0.0255(5) Uani 1 1 d . . .
H10 H 0.5694 0.7907 0.3214 0.031 Uiso 1 1 calc R . .
C11 C 0.6141(3) 0.5678(3) 0.36507(16) 0.0217(5) Uani 1 1 d . . .
C12 C 0.5031(4) 0.2880(3) 0.27872(17) 0.0266(6) Uani 1 1 d . . .
H12 H 0.4364 0.2063 0.2219 0.032 Uiso 1 1 calc R . .
C13 C 0.5845(4) 0.2236(3) 0.35790(17) 0.0280(6) Uani 1 1 d . . .
H13 H 0.5672 0.0996 0.3522 0.034 Uiso 1 1 calc R . .
O1W O 0.2089(3) 0.1256(3) 0.03149(16) 0.0572(6) Uani 1 1 d . . .
H1W1 H 0.3228 0.0722 0.0574 0.086 Uiso 1 1 d R . .
H2W1 H 0.1123 0.0406 -0.0307 0.086 Uiso 1 1 d 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 C1 1.700(3) . ?
O1 N4 1.402(2) . ?
O1 H1 0.8407 . ?
N1 C1 1.323(3) . ?
N1 H1A 0.8805 . ?
N1 H1B 0.8805 . ?
N2 C1 1.354(3) . ?
N2 N3 1.382(3) . ?
N2 H2 0.8799 . ?
N3 C2 1.298(3) . ?
N4 C3 1.287(3) . ?
C2 C3 1.483(3) . ?
C2 C4 1.508(3) . ?
C3 C5 1.495(3) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
N5 C13 1.316(3) . ?
N5 C6 1.376(3) . ?
N6 C12 1.317(3) . ?
N6 C11 1.374(3) . ?
C6 C7 1.414(3) . ?
C6 C11 1.423(3) . ?
C7 C8 1.366(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.417(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.373(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.411(3) . ?
C10 H10 0.9500 . ?
C12 C13 1.419(3) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
O1W H1W1 1.1110 . ?
O1W H2W1 1.0542 . ?

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
N4 O1 H1 109.4 . . ?
C1 N1 H1A 119.9 . . ?
C1 N1 H1B 120.1 . . ?
H1A N1 H1B 120.0 . . ?
C1 N2 N3 119.9(2) . . ?
C1 N2 H2 120.1 . . ?
N3 N2 H2 120.0 . . ?
C2 N3 N2 116.5(2) . . ?
C3 N4 O1 113.39(19) . . ?
N1 C1 N2 117.9(2) . . ?
N1 C1 S1 123.17(18) . . ?
N2 C1 S1 118.95(18) . . ?
N3 C2 C3 115.4(2) . . ?
N3 C2 C4 124.6(2) . . ?
C3 C2 C4 120.0(2) . . ?
N4 C3 C2 113.2(2) . . ?
N4 C3 C5 125.7(2) . . ?
C2 C3 C5 121.0(2) . . ?
C2 C4 H4A 109.5 . . ?
C2 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C2 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C3 C5 H5A 109.5 . . ?
C3 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C3 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C13 N5 C6 116.0(2) . . ?
C12 N6 C11 116.0(2) . . ?
N5 C6 C7 119.8(2) . . ?
N5 C6 C11 120.9(2) . . ?
C7 C6 C11 119.3(2) . . ?
C8 C7 C6 120.1(2) . . ?
C8 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
C7 C8 C9 120.5(2) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 H8 119.7 . . ?
C10 C9 C8 120.6(2) . . ?
C10 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
C9 C10 C11 119.8(2) . . ?
C9 C10 H10 120.1 . . ?
C11 C10 H10 120.1 . . ?
N6 C11 C10 119.0(2) . . ?
N6 C11 C6 121.4(2) . . ?
C10 C11 C6 119.5(2) . . ?
N6 C12 C13 122.6(2) . . ?
N6 C12 H12 118.7 . . ?
C13 C12 H12 118.7 . . ?
N5 C13 C12 123.1(2) . . ?
N5 C13 H13 118.5 . . ?
C12 C13 H13 118.5 . . ?
H1W1 O1W H2W1 107.5 . . ?

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
C1 N2 N3 C2 174.2(2) . . . . ?
N3 N2 C1 N1 -4.7(3) . . . . ?
N3 N2 C1 S1 175.80(15) . . . . ?
N2 N3 C2 C3 176.12(18) . . . . ?
N2 N3 C2 C4 -3.2(3) . . . . ?
O1 N4 C3 C2 178.46(18) . . . . ?
O1 N4 C3 C5 0.9(3) . . . . ?
N3 C2 C3 N4 -173.8(2) . . . . ?
C4 C2 C3 N4 5.6(3) . . . . ?
N3 C2 C3 C5 4.0(3) . . . . ?
C4 C2 C3 C5 -176.7(2) . . . . ?
C13 N5 C6 C7 178.7(2) . . . . ?
C13 N5 C6 C11 0.1(3) . . . . ?
N5 C6 C7 C8 -177.6(2) . . . . ?
C11 C6 C7 C8 1.1(3) . . . . ?
C6 C7 C8 C9 0.1(4) . . . . ?
C7 C8 C9 C10 -1.1(4) . . . . ?
C8 C9 C10 C11 1.0(4) . . . . ?
C12 N6 C11 C10 -177.4(2) . . . . ?
C12 N6 C11 C6 1.6(3) . . . . ?
C9 C10 C11 N6 179.3(2) . . . . ?
C9 C10 C11 C6 0.2(4) . . . . ?
N5 C6 C11 N6 -1.6(3) . . . . ?
C7 C6 C11 N6 179.7(2) . . . . ?
N5 C6 C11 C10 177.4(2) . . . . ?
C7 C6 C11 C10 -1.2(3) . . . . ?
C11 N6 C12 C13 -0.2(3) . . . . ?
C6 N5 C13 C12 1.3(4) . . . . ?
N6 C12 C13 N5 -1.4(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.959
_diffrn_reflns_theta_full        28.36
_diffrn_measured_fraction_theta_full 0.959
_refine_diff_density_max         0.859
_refine_diff_density_min         -0.412
_refine_diff_density_rms         0.084
_database_code_depnum_ccdc_archive 'CCDC 974652'
