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

#######################################################################
#
#                 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_ts101_9b

_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C6 H5 N3 S'
_chemical_formula_sum            'C6 H5 N3 S'
_chemical_melting_point          ?

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow

_diffrn_ambient_temperature      293(2)
_chemical_formula_weight         151.19

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 c c n'
_symmetry_space_group_name_Hall  '-P 2ab 2ac'
_symmetry_int_tables_number      56
_chemical_absolute_configuration ?

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

_cell_length_a                   12.9346(4)
_cell_length_b                   21.7846(8)
_cell_length_c                   4.7923(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1350.35(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5476
_cell_measurement_theta_min      3.22
_cell_measurement_theta_max      27.50
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.487
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             624
_exptl_absorpt_coefficient_mu    0.393

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8587
_exptl_absorpt_correction_T_max  0.9434
_exptl_absorpt_process_details   'Bruker SADABS'

_exptl_special_details           
; 
 ? 
;


_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Apex DUO CCD area-detector'
_diffrn_measurement_method       'φ scans'
_diffrn_detector_area_resol_mean 25
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            9160
_diffrn_reflns_av_R_equivalents  0.0288
_diffrn_reflns_av_sigmaI/netI    0.0189
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       4
_diffrn_reflns_theta_min         3.22
_diffrn_reflns_theta_max         27.51
_reflns_number_total             1546
_reflns_number_gt                1411
_reflns_threshold_expression     >2σ(I)


_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_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)+(0.0612P)²+0.4174P] 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         1546
_refine_ls_number_parameters     91
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0381
_refine_ls_R_factor_gt           0.0352
_refine_ls_wR_factor_ref         0.1043
_refine_ls_wR_factor_gt          0.1017
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_restrained_S_all      1.082
_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
N1 N 0.51076(11) 0.45221(5) 0.7681(3) 0.0398(3) Uani 1 1 d . . .
S2 S 0.38910(3) 0.449984(17) 0.83976(9) 0.04102(17) Uani 1 1 d . . .
N3 N 0.35142(10) 0.39573(6) 0.6323(2) 0.0346(3) Uani 1 1 d . . .
N4 N 0.34780(9) 0.29888(6) 0.2239(3) 0.0339(3) Uani 1 1 d . . .
H4A H 0.3487 0.2689 0.1073 0.041 Uiso 1 1 calc R . .
H4B H 0.2906 0.3098 0.3008 0.041 Uiso 1 1 calc R . .
C4 C 0.43862(10) 0.32963(6) 0.2881(3) 0.0288(3) Uani 1 1 d . . .
C5 C 0.53327(12) 0.31573(7) 0.1771(3) 0.0380(3) Uani 1 1 d . . .
H5 H 0.5381 0.2848 0.0437 0.046 Uiso 1 1 calc R . .
C6 C 0.62441(12) 0.34729(8) 0.2605(4) 0.0452(4) Uani 1 1 d . . .
H6 H 0.6870 0.3358 0.1807 0.054 Uiso 1 1 calc R . .
C7 C 0.62422(11) 0.39335(8) 0.4510(4) 0.0436(4) Uani 1 1 d . . .
H7 H 0.6847 0.4138 0.4992 0.052 Uiso 1 1 calc R . .
C3A C 0.43612(10) 0.37678(6) 0.4951(3) 0.0277(3) Uani 1 1 d . . .
C7A C 0.52825(11) 0.40896(6) 0.5733(3) 0.0330(3) Uani 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
N1 0.0462(7) 0.0325(6) 0.0408(7) -0.0012(5) -0.0096(6) -0.0079(5)
S2 0.0489(3) 0.0364(3) 0.0377(3) -0.00886(14) -0.00136(15) -0.00232(14)
N3 0.0359(6) 0.0358(6) 0.0320(6) -0.0038(5) -0.0003(5) -0.0029(5)
N4 0.0340(6) 0.0346(6) 0.0331(6) -0.0059(5) -0.0002(5) -0.0078(5)
C4 0.0330(7) 0.0265(6) 0.0270(6) 0.0041(5) -0.0011(5) -0.0035(5)
C5 0.0381(7) 0.0340(7) 0.0419(8) -0.0009(6) 0.0055(6) 0.0000(6)
C6 0.0303(7) 0.0447(9) 0.0607(11) 0.0030(8) 0.0073(7) 0.0007(6)
C7 0.0300(7) 0.0426(8) 0.0580(10) 0.0054(7) -0.0056(7) -0.0081(6)
C3A 0.0301(6) 0.0266(6) 0.0265(6) 0.0045(5) -0.0030(5) -0.0029(5)
C7A 0.0357(7) 0.0285(6) 0.0348(7) 0.0040(5) -0.0076(6) -0.0057(5)

_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
N1 C7A 1.346(2) . ?
N1 S2 1.6113(15) . ?
S2 N3 1.6196(12) . ?
N3 C3A 1.3428(18) . ?
N4 C4 1.3868(17) . ?
N4 H4A 0.8600 . ?
N4 H4B 0.8600 . ?
C4 C5 1.369(2) . ?
C4 C3A 1.4283(18) . ?
C5 C6 1.422(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.357(3) . ?
C6 H6 0.9300 . ?
C7 C7A 1.414(2) . ?
C7 H7 0.9300 . ?
C3A C7A 1.4324(17) . ?

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
C7A N1 S2 106.91(10) . . ?
N1 S2 N3 100.66(6) . . ?
C3A N3 S2 106.23(10) . . ?
C4 N4 H4A 120.0 . . ?
C4 N4 H4B 120.0 . . ?
H4A N4 H4B 120.0 . . ?
C5 C4 N4 124.38(13) . . ?
C5 C4 C3A 116.69(13) . . ?
N4 C4 C3A 118.83(12) . . ?
C4 C5 C6 121.69(15) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C7 C6 C5 123.05(14) . . ?
C7 C6 H6 118.5 . . ?
C5 C6 H6 118.5 . . ?
C6 C7 C7A 117.27(13) . . ?
C6 C7 H7 121.4 . . ?
C7A C7 H7 121.4 . . ?
N3 C3A C4 125.42(12) . . ?
N3 C3A C7A 113.58(12) . . ?
C4 C3A C7A 120.99(12) . . ?
N1 C7A C7 127.11(14) . . ?
N1 C7A C3A 112.61(13) . . ?
C7 C7A C3A 120.27(14) . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.25
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.437
_refine_diff_density_min         -0.412
_refine_diff_density_rms         0.048
_database_code_depnum_ccdc_archive 'CCDC 994141'
#######################################################################
#
#                 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_ts119b

_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C12 H10 Cl2 N6 S2 Zn'
_chemical_formula_sum            'C12 H10 Cl2 N6 S2 Zn'
_chemical_melting_point          ?

_exptl_crystal_description       plate
_exptl_crystal_colour            orange

_diffrn_ambient_temperature      150(2)
_chemical_formula_weight         438.65

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2/c'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_int_tables_number      15
_chemical_absolute_configuration ?

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

_cell_length_a                   27.5548(8)
_cell_length_b                   4.6491(2)
_cell_length_c                   12.4548(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.699(1)
_cell_angle_gamma                90.00
_cell_volume                     1556.49(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3512
_cell_measurement_theta_min      3.35
_cell_measurement_theta_max      32.57
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.872
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             880
_exptl_absorpt_coefficient_mu    2.195

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5588
_exptl_absorpt_correction_T_max  0.6934
_exptl_absorpt_process_details   'Bruker SADABS'

_exptl_special_details           
; 
 ? 
;


_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Nonius X8Apex CCD area-detector'
_diffrn_measurement_method       'φ scans'
_diffrn_detector_area_resol_mean 25
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            7745
_diffrn_reflns_av_R_equivalents  0.0319
_diffrn_reflns_av_sigmaI/netI    0.0345
_diffrn_reflns_limit_h_min       -41
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.03
_diffrn_reflns_theta_max         32.59
_reflns_number_total             2818
_reflns_number_gt                2470
_reflns_threshold_expression     >2σ(I)


_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_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)+(0.0270P)²+0.4178P] where P=(Fo²+2Fc²)/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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2818
_refine_ls_number_parameters     113
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0306
_refine_ls_R_factor_gt           0.0250
_refine_ls_wR_factor_ref         0.0640
_refine_ls_wR_factor_gt          0.0618
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_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
Zn1 Zn 0.0000 0.92393(5) 0.2500 0.01492(6) Uani 1 2 d S . .
Cl1 Cl -0.034887(12) 0.65387(7) 0.10452(3) 0.02094(8) Uani 1 1 d . . .
S1 S 0.194838(13) 1.00535(9) 0.46051(3) 0.02306(8) Uani 1 1 d . . .
N1 N 0.14265(4) 1.1068(3) 0.38186(10) 0.0194(2) Uani 1 1 d . . .
N1N N 0.05590(4) 1.1561(3) 0.20325(10) 0.0171(2) Uani 1 1 d . . .
N2 N 0.21290(4) 0.7658(3) 0.38265(10) 0.0222(2) Uani 1 1 d . . .
C1 C 0.13735(5) 0.9505(3) 0.28957(11) 0.0153(2) Uani 1 1 d . . .
C2 C 0.17749(5) 0.7545(3) 0.28915(11) 0.0172(2) Uani 1 1 d . . .
C3 C 0.17692(5) 0.5752(3) 0.19645(12) 0.0208(3) Uani 1 1 d . . .
H3 H 0.2031 0.4435 0.1951 0.025 Uiso 1 1 calc R . .
C4 C 0.13712(5) 0.5997(3) 0.10937(12) 0.0211(3) Uani 1 1 d . . .
H4 H 0.1359 0.4813 0.0467 0.025 Uiso 1 1 calc R . .
C5 C 0.09727(5) 0.7962(3) 0.10887(10) 0.0180(2) Uani 1 1 d . . .
H5 H 0.0706 0.8067 0.0459 0.022 Uiso 1 1 calc R . .
C6 C 0.09670(5) 0.9691(3) 0.19705(11) 0.0155(2) Uani 1 1 d . . .
H1N H 0.0442(7) 1.236(4) 0.1433(16) 0.029(5) Uiso 1 1 d . . .
H2N H 0.0642(6) 1.289(4) 0.2486(15) 0.022(4) 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
Zn1 0.01139(10) 0.01515(11) 0.01734(11) 0.000 0.00122(7) 0.000
Cl1 0.01970(15) 0.02092(16) 0.01995(15) -0.00447(11) -0.00049(12) -0.00085(11)
S1 0.01643(15) 0.02803(19) 0.02171(17) -0.00348(13) -0.00233(13) 0.00168(13)
N1 0.0150(5) 0.0209(6) 0.0211(6) -0.0018(4) 0.0012(4) 0.0003(4)
N1N 0.0142(5) 0.0145(5) 0.0210(6) 0.0019(4) 0.0007(4) 0.0007(4)
N2 0.0156(5) 0.0256(6) 0.0239(6) 0.0007(5) 0.0013(4) 0.0027(4)
C1 0.0123(5) 0.0161(6) 0.0174(6) 0.0011(4) 0.0031(4) -0.0009(4)
C2 0.0134(5) 0.0184(6) 0.0200(6) 0.0018(5) 0.0038(4) 0.0001(4)
C3 0.0182(6) 0.0209(7) 0.0252(7) 0.0006(5) 0.0085(5) 0.0036(5)
C4 0.0238(7) 0.0215(7) 0.0197(6) -0.0006(5) 0.0082(5) -0.0009(5)
C5 0.0180(6) 0.0197(6) 0.0157(6) 0.0016(5) 0.0023(5) -0.0014(5)
C6 0.0131(5) 0.0148(6) 0.0182(6) 0.0037(4) 0.0024(4) -0.0003(4)

_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
Zn1 N1N 2.0667(12) 2 ?
Zn1 N1N 2.0667(12) . ?
Zn1 Cl1 2.2400(3) . ?
Zn1 Cl1 2.2400(3) 2 ?
S1 N1 1.6219(12) . ?
S1 N2 1.6251(13) . ?
N1 C1 1.3403(18) . ?
N1N C6 1.4369(17) . ?
N1N H1N 0.83(2) . ?
N1N H2N 0.836(19) . ?
N2 C2 1.3460(17) . ?
C1 C6 1.4221(18) . ?
C1 C2 1.4339(18) . ?
C2 C3 1.4215(19) . ?
C3 C4 1.367(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.4273(19) . ?
C4 H4 0.9500 . ?
C5 C6 1.3639(19) . ?
C5 H5 0.9500 . ?

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
N1N Zn1 N1N 117.02(7) 2 . ?
N1N Zn1 Cl1 107.87(3) 2 . ?
N1N Zn1 Cl1 106.19(4) . . ?
N1N Zn1 Cl1 106.19(4) 2 2 ?
N1N Zn1 Cl1 107.87(3) . 2 ?
Cl1 Zn1 Cl1 111.82(2) . 2 ?
N1 S1 N2 100.73(6) . . ?
C1 N1 S1 105.98(9) . . ?
C6 N1N Zn1 109.85(8) . . ?
C6 N1N H1N 112.1(13) . . ?
Zn1 N1N H1N 108.6(13) . . ?
C6 N1N H2N 112.5(12) . . ?
Zn1 N1N H2N 107.9(12) . . ?
H1N N1N H2N 105.7(18) . . ?
C2 N2 S1 106.49(9) . . ?
N1 C1 C6 125.45(12) . . ?
N1 C1 C2 114.14(11) . . ?
C6 C1 C2 120.42(12) . . ?
N2 C2 C3 127.01(12) . . ?
N2 C2 C1 112.66(12) . . ?
C3 C2 C1 120.33(12) . . ?
C4 C3 C2 117.33(12) . . ?
C4 C3 H3 121.3 . . ?
C2 C3 H3 121.3 . . ?
C3 C4 C5 122.63(13) . . ?
C3 C4 H4 118.7 . . ?
C5 C4 H4 118.7 . . ?
C6 C5 C4 121.24(12) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C5 C6 C1 118.06(12) . . ?
C5 C6 N1N 123.20(12) . . ?
C1 C6 N1N 118.65(12) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.423
_refine_diff_density_min         -0.406
_refine_diff_density_rms         0.074
_database_code_depnum_ccdc_archive 'CCDC 994142'
#######################################################################
#
#                 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_ts100_4b

_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C6 H3 N3 O2 S'
_chemical_formula_sum            'C6 H3 N3 O2 S'
_chemical_melting_point          ?

_exptl_crystal_description       prism
_exptl_crystal_colour            'light yellow'

_diffrn_ambient_temperature      150(2)
_chemical_formula_weight         181.17

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   'P 21/c'
_symmetry_int_tables_number      14
_chemical_absolute_configuration ?
_symmetry_space_group_name_Hall  '-P 2ybc'

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                   4.6171(2)
_cell_length_b                   9.9885(4)
_cell_length_c                   14.8728(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.403(1)
_cell_angle_gamma                90.00
_cell_volume                     678.54(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3527
_cell_measurement_theta_min      2.46
_cell_measurement_theta_max      32.67
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.773
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             368
_exptl_absorpt_coefficient_mu    0.428

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8541
_exptl_absorpt_correction_T_max  0.9665
_exptl_absorpt_process_details   'Bruker SADABS'

_exptl_special_details           
; 
 ? 
;


_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Apex DUO CCD area-detector'
_diffrn_measurement_method       'φ scans'
_diffrn_detector_area_resol_mean 25
_diffrn_standards_number         0
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_reflns_number            6440
_diffrn_reflns_av_R_equivalents  0.0159
_diffrn_reflns_av_sigmaI/netI    0.0204
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.46
_diffrn_reflns_theta_max         32.80
_reflns_number_total             2465
_reflns_number_gt                2142
_reflns_threshold_expression     >2σ(I)


_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_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)+(0.0509P)²+0.1071P] 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         2465
_refine_ls_number_parameters     109
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0368
_refine_ls_R_factor_gt           0.0302
_refine_ls_wR_factor_ref         0.0839
_refine_ls_wR_factor_gt          0.0806
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_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
O1 O 0.2691(2) 0.79289(10) -0.07320(7) 0.0363(2) Uani 1 1 d . . .
N1 N 0.48176(19) 0.49513(9) 0.19865(6) 0.01739(16) Uani 1 1 d . . .
S2 S 0.22881(5) 0.45990(2) 0.115393(17) 0.01630(8) Uani 1 1 d . . .
O2 O 0.6532(2) 0.91855(9) -0.06507(6) 0.02758(19) Uani 1 1 d . . .
N3 N 0.26383(18) 0.58225(8) 0.04627(5) 0.01476(16) Uani 1 1 d . . .
N4 N 0.5042(2) 0.83291(9) -0.03386(6) 0.01829(17) Uani 1 1 d . . .
C4 C 0.6120(2) 0.77629(9) 0.05543(6) 0.01470(17) Uani 1 1 d . . .
C5 C 0.8431(2) 0.83766(10) 0.10761(7) 0.01785(18) Uani 1 1 d . . .
H5 H 0.9265 0.9156 0.0853 0.021 Uiso 1 1 calc R . .
C6 C 0.9604(2) 0.78675(11) 0.19461(7) 0.0196(2) Uani 1 1 d . . .
H6 H 1.1202 0.8317 0.2295 0.024 Uiso 1 1 calc R . .
C7 C 0.8481(2) 0.67455(11) 0.22911(7) 0.01795(19) Uani 1 1 d . . .
H7 H 0.9275 0.6412 0.2873 0.022 Uiso 1 1 calc R . .
C3A C 0.48423(19) 0.65874(9) 0.08752(6) 0.01261(16) Uani 1 1 d . . .
C7A C 0.6097(2) 0.60898(9) 0.17566(6) 0.01407(17) Uani 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
O1 0.0337(5) 0.0381(5) 0.0309(5) 0.0148(4) -0.0157(4) -0.0097(4)
N1 0.0166(4) 0.0187(4) 0.0162(4) 0.0016(3) 0.0001(3) 0.0017(3)
S2 0.01491(12) 0.01552(12) 0.01798(12) 0.00019(8) 0.00076(8) -0.00124(8)
O2 0.0325(5) 0.0266(4) 0.0252(4) 0.0074(3) 0.0095(3) -0.0022(3)
N3 0.0131(4) 0.0155(3) 0.0148(3) -0.0009(3) -0.0007(3) 0.0000(3)
N4 0.0215(4) 0.0158(4) 0.0174(4) 0.0010(3) 0.0023(3) 0.0030(3)
C4 0.0147(4) 0.0142(4) 0.0148(4) -0.0007(3) 0.0013(3) 0.0018(3)
C5 0.0156(4) 0.0163(4) 0.0217(4) -0.0038(3) 0.0032(3) -0.0014(3)
C6 0.0148(4) 0.0222(5) 0.0208(4) -0.0080(4) -0.0009(3) -0.0012(3)
C7 0.0153(4) 0.0227(5) 0.0145(4) -0.0044(3) -0.0025(3) 0.0023(3)
C3A 0.0109(4) 0.0142(4) 0.0124(4) -0.0020(3) 0.0005(3) 0.0019(3)
C7A 0.0123(4) 0.0163(4) 0.0131(4) -0.0012(3) -0.0001(3) 0.0024(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
O1 N4 1.2224(13) . ?
N1 C7A 1.3484(13) . ?
N1 S2 1.6119(9) . ?
S2 N3 1.6203(9) . ?
O2 N4 1.2304(12) . ?
N3 C3A 1.3465(12) . ?
N4 C4 1.4621(13) . ?
C4 C5 1.3692(13) . ?
C4 C3A 1.4271(13) . ?
C5 C6 1.4218(15) . ?
C5 H5 0.9500 . ?
C6 C7 1.3660(15) . ?
C6 H6 0.9500 . ?
C7 C7A 1.4201(13) . ?
C7 H7 0.9500 . ?
C3A C7A 1.4420(12) . ?

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
C7A N1 S2 106.53(7) . . ?
N1 S2 N3 101.21(5) . . ?
C3A N3 S2 106.12(6) . . ?
O1 N4 O2 123.58(9) . . ?
O1 N4 C4 117.95(9) . . ?
O2 N4 C4 118.47(9) . . ?
C5 C4 C3A 120.31(9) . . ?
C5 C4 N4 118.38(9) . . ?
C3A C4 N4 121.30(8) . . ?
C4 C5 C6 121.17(10) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C7 C6 C5 121.34(9) . . ?
C7 C6 H6 119.3 . . ?
C5 C6 H6 119.3 . . ?
C6 C7 C7A 118.29(9) . . ?
C6 C7 H7 120.9 . . ?
C7A C7 H7 120.9 . . ?
N3 C3A C4 129.50(8) . . ?
N3 C3A C7A 113.28(8) . . ?
C4 C3A C7A 117.19(8) . . ?
N1 C7A C7 125.42(9) . . ?
N1 C7A C3A 112.86(8) . . ?
C7 C7A C3A 121.71(9) . . ?

_diffrn_measured_fraction_theta_max 0.984
_diffrn_reflns_theta_full        25.25
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.599
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.065
_diffrn_radiation_source         'fine-focus sealed tube'

_database_code_depnum_ccdc_archive 'CCDC 994143'
#######################################################################
#
#                 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_ts101

_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H8 N6 O2 S2'
_chemical_melting_point          ?

_exptl_crystal_description       plate
_exptl_crystal_colour            'dark red'

_diffrn_ambient_temperature      293(2)
_chemical_formula_weight         332.36

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'
N N 0.0061 0.0033 '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'
S S 0.1246 0.1234 '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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_int_tables_number      2
_chemical_absolute_configuration ?

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

_cell_length_a                   7.4742(2)
_cell_length_b                   8.3487(3)
_cell_length_c                   11.8518(4)
_cell_angle_alpha                82.880(2)
_cell_angle_beta                 79.480(2)
_cell_angle_gamma                69.068(1)
_cell_volume                     677.74(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2423
_cell_measurement_theta_min      2.62
_cell_measurement_theta_max      27.37
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.629
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             340
_exptl_absorpt_coefficient_mu    0.410

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8698
_exptl_absorpt_correction_T_max  0.9838
_exptl_absorpt_process_details   'Bruker SADABS'

_exptl_special_details           
; 
 ? 
;


_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Nonius X8Apex CCD area-detector'
_diffrn_measurement_method       'φ scans'
_diffrn_detector_area_resol_mean 25
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            5604
_diffrn_reflns_av_R_equivalents  0.0304
_diffrn_reflns_av_sigmaI/netI    0.0429
_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       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.62
_diffrn_reflns_theta_max         26.37
_reflns_number_total             2754
_reflns_number_gt                2144
_reflns_threshold_expression     >2σ(I)


_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_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)+(0.0432P)²+0.0905P] 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     ?
_refine_ls_extinction_coef       ?
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2754
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0509
_refine_ls_R_factor_gt           0.0360
_refine_ls_wR_factor_ref         0.0925
_refine_ls_wR_factor_gt          0.0879
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_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 -0.03690(8) 1.19027(6) 0.27225(5) 0.04986(18) Uani 1 1 d . . .
S2 S 0.77431(7) 0.71654(6) 0.01633(4) 0.04292(17) Uani 1 1 d . . .
N11 N -0.0989(2) 1.0612(2) 0.37125(14) 0.0458(4) Uani 1 1 d . . .
C11 C -0.0312(2) 0.9049(2) 0.32798(15) 0.0343(4) Uani 1 1 d . . .
N12 N 0.0758(2) 1.06152(19) 0.17109(14) 0.0399(4) Uani 1 1 d . . .
C12 C 0.0685(2) 0.9064(2) 0.21240(15) 0.0321(4) Uani 1 1 d . . .
N13 N 0.2453(2) 0.7613(2) 0.04131(14) 0.0491(4) Uani 1 1 d . . .
H13A H 0.2966 0.6700 0.0036 0.059 Uiso 1 1 calc R . .
H13B H 0.2536 0.8575 0.0100 0.059 Uiso 1 1 calc R . .
C13 C 0.1510(3) 0.7535(2) 0.15034(16) 0.0353(4) Uani 1 1 d . . .
C14 C 0.1284(3) 0.6076(2) 0.20919(17) 0.0421(5) Uani 1 1 d . . .
H14 H 0.1796 0.5049 0.1727 0.051 Uiso 1 1 calc R . .
C15 C 0.0302(3) 0.6078(3) 0.32313(17) 0.0448(5) Uani 1 1 d . . .
H15 H 0.0199 0.5049 0.3583 0.054 Uiso 1 1 calc R . .
C16 C -0.0501(3) 0.7512(3) 0.38406(17) 0.0430(5) Uani 1 1 d . . .
H16 H -0.1143 0.7479 0.4589 0.052 Uiso 1 1 calc R . .
O21 O 0.5466(2) 1.19170(18) 0.19312(13) 0.0636(5) Uani 1 1 d . . .
N21 N 0.7081(2) 0.58134(19) 0.10701(14) 0.0418(4) Uani 1 1 d . . .
C21 C 0.6119(2) 0.6666(2) 0.20185(16) 0.0336(4) Uani 1 1 d . . .
O22 O 0.4027(2) 1.20675(19) 0.36670(14) 0.0623(5) Uani 1 1 d . . .
N22 N 0.6889(2) 0.88696(19) 0.08725(13) 0.0348(4) Uani 1 1 d . . .
C22 C 0.6015(2) 0.8430(2) 0.19001(15) 0.0291(4) Uani 1 1 d . . .
N23 N 0.4825(2) 1.12697(19) 0.28080(14) 0.0362(4) Uani 1 1 d . . .
C23 C 0.5034(2) 0.9452(2) 0.28533(15) 0.0300(4) Uani 1 1 d . . .
C24 C 0.4253(2) 0.8742(2) 0.38303(16) 0.0364(4) Uani 1 1 d . . .
H24 H 0.3624 0.9416 0.4450 0.044 Uiso 1 1 calc R . .
C25 C 0.4381(3) 0.7006(3) 0.39176(17) 0.0411(5) Uani 1 1 d . . .
H25 H 0.3836 0.6560 0.4595 0.049 Uiso 1 1 calc R . .
C26 C 0.5281(3) 0.5971(2) 0.30383(17) 0.0394(4) Uani 1 1 d . . .
H26 H 0.5345 0.4831 0.3104 0.047 Uiso 1 1 calc R . .

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
S1 0.0580(3) 0.0345(3) 0.0526(4) -0.0098(2) 0.0012(3) -0.0128(2)
S2 0.0568(3) 0.0370(3) 0.0323(3) -0.0106(2) 0.0060(2) -0.0163(2)
N11 0.0470(9) 0.0457(10) 0.0382(10) -0.0109(8) 0.0025(8) -0.0095(8)
C11 0.0330(9) 0.0383(10) 0.0293(10) -0.0041(8) -0.0033(7) -0.0096(8)
N12 0.0430(9) 0.0367(9) 0.0375(9) -0.0014(7) -0.0010(7) -0.0134(7)
C12 0.0310(9) 0.0335(9) 0.0315(10) -0.0005(8) -0.0050(7) -0.0112(7)
N13 0.0648(11) 0.0440(10) 0.0313(10) -0.0103(8) 0.0080(8) -0.0149(8)
C13 0.0362(9) 0.0378(10) 0.0305(10) -0.0049(8) -0.0049(8) -0.0100(8)
C14 0.0536(12) 0.0327(10) 0.0406(12) -0.0079(9) -0.0082(9) -0.0132(9)
C15 0.0545(12) 0.0405(11) 0.0428(12) 0.0057(9) -0.0090(10) -0.0225(9)
C16 0.0451(11) 0.0510(12) 0.0321(11) 0.0020(9) 0.0007(9) -0.0203(9)
O21 0.1040(12) 0.0383(8) 0.0432(9) -0.0062(7) 0.0186(9) -0.0311(8)
N21 0.0512(9) 0.0338(8) 0.0396(10) -0.0076(7) -0.0004(7) -0.0149(7)
C21 0.0355(9) 0.0304(9) 0.0344(10) -0.0031(8) -0.0046(8) -0.0108(7)
O22 0.0855(11) 0.0455(8) 0.0490(9) -0.0218(7) 0.0177(8) -0.0215(8)
N22 0.0412(8) 0.0334(8) 0.0276(8) -0.0050(6) 0.0016(6) -0.0125(7)
C22 0.0297(8) 0.0309(9) 0.0271(9) -0.0020(7) -0.0050(7) -0.0104(7)
N23 0.0402(8) 0.0327(8) 0.0336(9) -0.0073(7) -0.0009(7) -0.0106(7)
C23 0.0297(8) 0.0307(9) 0.0285(9) -0.0018(7) -0.0051(7) -0.0089(7)
C24 0.0359(9) 0.0411(10) 0.0283(10) -0.0028(8) -0.0004(8) -0.0104(8)
C25 0.0413(10) 0.0451(11) 0.0341(11) 0.0088(9) -0.0014(8) -0.0172(9)
C26 0.0433(10) 0.0327(9) 0.0421(11) 0.0039(8) -0.0059(9) -0.0151(8)

_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 N11 1.6113(17) . ?
S1 N12 1.6144(16) . ?
S2 N21 1.6058(16) . ?
S2 N22 1.6093(15) . ?
N11 C11 1.350(2) . ?
C11 C16 1.412(3) . ?
C11 C12 1.436(2) . ?
N12 C12 1.343(2) . ?
C12 C13 1.434(2) . ?
N13 C13 1.360(2) . ?
N13 H13A 0.8600 . ?
N13 H13B 0.8600 . ?
C13 C14 1.376(3) . ?
C14 C15 1.414(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.362(3) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
O21 N23 1.211(2) . ?
N21 C21 1.351(2) . ?
C21 C26 1.414(2) . ?
C21 C22 1.437(2) . ?
O22 N23 1.2240(19) . ?
N22 C22 1.347(2) . ?
C22 C23 1.425(2) . ?
N23 C23 1.464(2) . ?
C23 C24 1.365(2) . ?
C24 C25 1.409(3) . ?
C24 H24 0.9300 . ?
C25 C26 1.356(3) . ?
C25 H25 0.9300 . ?
C26 H26 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
N11 S1 N12 101.08(8) . . ?
N21 S2 N22 101.38(8) . . ?
C11 N11 S1 106.61(13) . . ?
N11 C11 C16 126.95(17) . . ?
N11 C11 C12 112.52(16) . . ?
C16 C11 C12 120.53(17) . . ?
C12 N12 S1 106.20(13) . . ?
N12 C12 C13 124.91(16) . . ?
N12 C12 C11 113.59(16) . . ?
C13 C12 C11 121.50(16) . . ?
C13 N13 H13A 120.0 . . ?
C13 N13 H13B 120.0 . . ?
H13A N13 H13B 120.0 . . ?
N13 C13 C14 125.26(17) . . ?
N13 C13 C12 119.27(16) . . ?
C14 C13 C12 115.47(16) . . ?
C13 C14 C15 122.45(18) . . ?
C13 C14 H14 118.8 . . ?
C15 C14 H14 118.8 . . ?
C16 C15 C14 123.37(18) . . ?
C16 C15 H15 118.3 . . ?
C14 C15 H15 118.3 . . ?
C15 C16 C11 116.68(17) . . ?
C15 C16 H16 121.7 . . ?
C11 C16 H16 121.7 . . ?
C21 N21 S2 106.58(12) . . ?
N21 C21 C26 126.04(16) . . ?
N21 C21 C22 112.54(16) . . ?
C26 C21 C22 121.42(17) . . ?
C22 N22 S2 106.19(11) . . ?
N22 C22 C23 129.39(15) . . ?
N22 C22 C21 113.31(15) . . ?
C23 C22 C21 117.31(15) . . ?
O21 N23 O22 122.68(16) . . ?
O21 N23 C23 118.90(15) . . ?
O22 N23 C23 118.42(15) . . ?
C24 C23 C22 119.96(16) . . ?
C24 C23 N23 118.70(16) . . ?
C22 C23 N23 121.34(14) . . ?
C23 C24 C25 121.27(17) . . ?
C23 C24 H24 119.4 . . ?
C25 C24 H24 119.4 . . ?
C26 C25 C24 121.63(17) . . ?
C26 C25 H25 119.2 . . ?
C24 C25 H25 119.2 . . ?
C25 C26 C21 118.41(17) . . ?
C25 C26 H26 120.8 . . ?
C21 C26 H26 120.8 . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        25.25
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.230
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.043
_database_code_depnum_ccdc_archive 'CCDC 994144'
