# Electronic Supplementary Material for CrystEngComm
# This journal is (c) The Royal Society of Chemistry 2008

data_global

_journal_coden_Cambridge         1350
_journal_volume                  ?
_journal_page_first              ?
_journal_year                    ?

loop_
_publ_author_name
'Thomas Gelbrich'
'David S Hughes'
'Mike Hursthouse'
'T Threlfall'

_publ_contact_author_name        'Thomas Gelbrich'
_publ_contact_author_email       GELBRICH@SOTON.AC.UK

_publ_section_title              
;
Packing similarity in polymorphs of sulfathiazole
;

# Attachment 'sulfathiazole.cif'

data_form_I
_database_code_depnum_ccdc_archive 'CCDC 687586'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H9 N3 O2 S2'
_chemical_formula_weight         255.31

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                   10.534(2)
_cell_length_b                   12.936(3)
_cell_length_c                   17.191(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.77(3)
_cell_angle_gamma                90.00
_cell_volume                     2230.8(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.520
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1056
_exptl_absorpt_coefficient_mu    0.465
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8926
_exptl_absorpt_correction_T_max  0.9637
_exptl_absorpt_process_details   'SADABS V2.10 (Sheldrick, 2003)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      150(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            19523
_diffrn_reflns_av_R_equivalents  0.0878
_diffrn_reflns_av_sigmaI/netI    0.0627
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.94
_diffrn_reflns_theta_max         25.03
_reflns_number_total             3938
_reflns_number_gt                2890
_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)+(0.0521P)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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3938
_refine_ls_number_parameters     361
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0646
_refine_ls_R_factor_gt           0.0400
_refine_ls_wR_factor_ref         0.1016
_refine_ls_wR_factor_gt          0.0917
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_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
S11 S 0.69239(6) 0.57187(5) -0.08959(4) 0.02329(18) Uani 1 1 d . . .
S12 S 0.84723(7) 0.75569(5) 0.03577(4) 0.0300(2) Uani 1 1 d . . .
S21 S 0.81776(6) 0.07347(5) 0.11850(4) 0.02438(19) Uani 1 1 d . . .
S22 S 0.63514(7) 0.08306(7) -0.07338(5) 0.0379(2) Uani 1 1 d . . .
O11 O 0.66220(17) 0.46787(14) -0.11992(11) 0.0313(5) Uani 1 1 d . . .
O12 O 0.62019(17) 0.61186(15) -0.03712(11) 0.0320(5) Uani 1 1 d . . .
O21 O 0.91444(18) 0.03367(14) 0.19157(11) 0.0337(5) Uani 1 1 d . . .
O22 O 0.68019(17) 0.04393(14) 0.10245(11) 0.0315(5) Uani 1 1 d . . .
N11 N 0.5716(2) 0.8423(2) -0.38022(16) 0.0311(6) Uani 1 1 d . . .
N12 N 0.85087(19) 0.57011(16) -0.04551(12) 0.0217(5) Uani 1 1 d . . .
N13 N 1.0391(2) 0.63256(19) 0.05217(14) 0.0261(5) Uani 1 1 d . . .
N21 N 0.8434(3) 0.52760(19) 0.15165(15) 0.0295(6) Uani 1 1 d . . .
N22 N 0.8744(2) 0.03564(16) 0.04598(13) 0.0243(5) Uani 1 1 d . . .
N23 N 0.8466(2) 0.01147(17) -0.09147(13) 0.0251(5) Uani 1 1 d . . .
C11 C 0.5977(2) 0.7778(2) -0.31347(16) 0.0234(6) Uani 1 1 d . . .
C12 C 0.6640(2) 0.6845(2) -0.31092(16) 0.0224(6) Uani 1 1 d . . .
C13 C 0.6944(2) 0.6225(2) -0.24236(15) 0.0210(6) Uani 1 1 d . . .
C14 C 0.6594(2) 0.65395(19) -0.17450(15) 0.0208(6) Uani 1 1 d . . .
C15 C 0.5924(3) 0.7465(2) -0.17654(17) 0.0256(6) Uani 1 1 d . . .
C16 C 0.5602(3) 0.8072(2) -0.24508(16) 0.0268(6) Uani 1 1 d . . .
C17 C 0.9102(2) 0.64180(19) 0.00850(15) 0.0215(6) Uani 1 1 d . . .
C18 C 1.0876(3) 0.7089(2) 0.10979(18) 0.0326(7) Uani 1 1 d . . .
C19 C 0.9986(3) 0.7810(2) 0.10922(19) 0.0337(7) Uani 1 1 d . . .
C21 C 0.8373(2) 0.4232(2) 0.13989(15) 0.0224(6) Uani 1 1 d . . .
C22 C 0.9523(3) 0.3621(2) 0.16839(16) 0.0254(6) Uani 1 1 d . . .
C23 C 0.9471(3) 0.2572(2) 0.15965(17) 0.0253(6) Uani 1 1 d . . .
C24 C 0.8260(2) 0.2082(2) 0.12317(15) 0.0210(6) Uani 1 1 d . . .
C25 C 0.7110(3) 0.2675(2) 0.09268(16) 0.0250(6) Uani 1 1 d . . .
C26 C 0.7169(3) 0.3732(2) 0.10050(17) 0.0274(6) Uani 1 1 d . . .
C27 C 0.7984(2) 0.0408(2) -0.03194(16) 0.0235(6) Uani 1 1 d . . .
C28 C 0.7626(3) 0.0268(2) -0.16958(18) 0.0307(7) Uani 1 1 d . . .
C29 C 0.6454(3) 0.0657(2) -0.17146(18) 0.0371(7) Uani 1 1 d . . .
H10 H 0.501(3) 0.890(3) -0.386(2) 0.054(10) Uiso 1 1 d . . .
H11 H 0.580(3) 0.815(2) -0.4230(19) 0.039(9) Uiso 1 1 d . . .
H12 H 0.685(2) 0.6612(19) -0.3570(16) 0.022(7) Uiso 1 1 d . . .
H13 H 0.739(2) 0.5590(19) -0.2414(15) 0.019(7) Uiso 1 1 d . . .
H15 H 0.566(2) 0.7633(18) -0.1333(16) 0.018(7) Uiso 1 1 d . . .
H16 H 0.507(2) 0.867(2) -0.2491(16) 0.029(7) Uiso 1 1 d . . .
H17 H 1.083(3) 0.578(2) 0.0520(17) 0.029(8) Uiso 1 1 d . . .
H18 H 1.174(3) 0.700(2) 0.1446(18) 0.038(8) Uiso 1 1 d . . .
H19 H 1.008(2) 0.837(2) 0.1424(16) 0.026(7) Uiso 1 1 d . . .
H20 H 0.764(3) 0.566(2) 0.1360(17) 0.030(8) Uiso 1 1 d . . .
H21 H 0.919(3) 0.555(2) 0.1818(19) 0.039(9) Uiso 1 1 d . . .
H22 H 1.033(3) 0.397(2) 0.1948(17) 0.029(7) Uiso 1 1 d . . .
H23 H 1.022(3) 0.217(2) 0.1784(16) 0.029(7) Uiso 1 1 d . . .
H25 H 0.629(3) 0.235(2) 0.0700(18) 0.035(8) Uiso 1 1 d . . .
H26 H 0.640(3) 0.416(2) 0.0812(17) 0.032(8) Uiso 1 1 d . . .
H27 H 0.929(3) -0.011(2) -0.0800(18) 0.043(9) Uiso 1 1 d . . .
H28 H 0.793(3) 0.006(2) -0.2127(17) 0.029(7) Uiso 1 1 d . . .
H29 H 0.569(3) 0.079(3) -0.216(2) 0.067(11) 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
S11 O12 1.4417(19) . ?
S11 O11 1.4427(19) . ?
S11 N12 1.609(2) . ?
S11 C14 1.752(3) . ?
S12 C19 1.737(3) . ?
S12 C17 1.738(3) . ?
S21 O22 1.4417(18) . ?
S21 O21 1.4489(19) . ?
S21 N22 1.613(2) . ?
S21 C24 1.746(3) . ?
S22 C27 1.736(2) . ?
S22 C29 1.737(3) . ?
N11 C11 1.377(3) . ?
N11 H10 0.95(3) . ?
N11 H11 0.84(3) . ?
N12 C17 1.326(3) . ?
N13 C17 1.342(3) . ?
N13 C18 1.382(4) . ?
N13 H17 0.85(3) . ?
N21 C21 1.365(3) . ?
N21 H20 0.94(3) . ?
N21 H21 0.88(3) . ?
N22 C27 1.336(3) . ?
N23 C27 1.329(3) . ?
N23 C28 1.378(3) . ?
N23 H27 0.88(3) . ?
C11 C12 1.388(4) . ?
C11 C16 1.403(4) . ?
C12 C13 1.380(4) . ?
C12 H12 0.94(3) . ?
C13 C14 1.387(3) . ?
C13 H13 0.95(2) . ?
C14 C15 1.385(4) . ?
C15 C16 1.369(4) . ?
C15 H15 0.90(2) . ?
C16 H16 0.94(3) . ?
C18 C19 1.320(4) . ?
C18 H18 0.93(3) . ?
C19 H19 0.91(3) . ?
C21 C26 1.400(4) . ?
C21 C22 1.403(4) . ?
C22 C23 1.364(4) . ?
C22 H22 0.95(3) . ?
C23 C24 1.391(4) . ?
C23 H23 0.92(3) . ?
C24 C25 1.394(4) . ?
C25 C26 1.373(4) . ?
C25 H25 0.94(3) . ?
C26 H26 0.95(3) . ?
C28 C29 1.324(4) . ?
C28 H28 0.93(3) . ?
C29 H29 0.94(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
O12 S11 O11 117.42(11) . . ?
O12 S11 N12 112.33(11) . . ?
O11 S11 N12 103.86(11) . . ?
O12 S11 C14 107.19(12) . . ?
O11 S11 C14 107.36(12) . . ?
N12 S11 C14 108.32(11) . . ?
C19 S12 C17 90.85(13) . . ?
O22 S21 O21 118.12(12) . . ?
O22 S21 N22 111.02(11) . . ?
O21 S21 N22 103.55(11) . . ?
O22 S21 C24 107.83(11) . . ?
O21 S21 C24 107.64(12) . . ?
N22 S21 C24 108.27(11) . . ?
C27 S22 C29 90.58(14) . . ?
C11 N11 H10 115.7(19) . . ?
C11 N11 H11 115(2) . . ?
H10 N11 H11 118(3) . . ?
C17 N12 S11 121.28(18) . . ?
C17 N13 C18 115.3(2) . . ?
C17 N13 H17 122.2(19) . . ?
C18 N13 H17 121.2(19) . . ?
C21 N21 H20 118.8(17) . . ?
C21 N21 H21 118.5(19) . . ?
H20 N21 H21 122(3) . . ?
C27 N22 S21 120.65(18) . . ?
C27 N23 C28 115.3(2) . . ?
C27 N23 H27 120(2) . . ?
C28 N23 H27 124(2) . . ?
N11 C11 C12 121.6(2) . . ?
N11 C11 C16 119.9(3) . . ?
C12 C11 C16 118.5(2) . . ?
C13 C12 C11 121.0(2) . . ?
C13 C12 H12 118.8(15) . . ?
C11 C12 H12 120.1(15) . . ?
C12 C13 C14 119.7(2) . . ?
C12 C13 H13 120.3(15) . . ?
C14 C13 H13 120.0(15) . . ?
C15 C14 C13 119.8(2) . . ?
C15 C14 S11 120.99(19) . . ?
C13 C14 S11 119.1(2) . . ?
C16 C15 C14 120.5(3) . . ?
C16 C15 H15 121.0(16) . . ?
C14 C15 H15 118.3(16) . . ?
C15 C16 C11 120.4(3) . . ?
C15 C16 H16 121.2(16) . . ?
C11 C16 H16 118.2(16) . . ?
N12 C17 N13 120.6(2) . . ?
N12 C17 S12 130.15(19) . . ?
N13 C17 S12 109.21(19) . . ?
C19 C18 N13 113.2(3) . . ?
C19 C18 H18 130.0(18) . . ?
N13 C18 H18 116.7(18) . . ?
C18 C19 S12 111.4(2) . . ?
C18 C19 H19 128.3(17) . . ?
S12 C19 H19 120.2(16) . . ?
N21 C21 C26 121.5(2) . . ?
N21 C21 C22 120.6(2) . . ?
C26 C21 C22 117.9(3) . . ?
C23 C22 C21 121.3(2) . . ?
C23 C22 H22 121.9(16) . . ?
C21 C22 H22 116.8(16) . . ?
C22 C23 C24 120.3(3) . . ?
C22 C23 H23 121.7(17) . . ?
C24 C23 H23 118.0(17) . . ?
C23 C24 C25 119.4(3) . . ?
C23 C24 S21 120.1(2) . . ?
C25 C24 S21 120.5(2) . . ?
C26 C25 C24 120.2(3) . . ?
C26 C25 H25 120.1(17) . . ?
C24 C25 H25 119.6(17) . . ?
C25 C26 C21 120.9(3) . . ?
C25 C26 H26 122.1(17) . . ?
C21 C26 H26 117.0(17) . . ?
N23 C27 N22 120.3(2) . . ?
N23 C27 S22 109.70(19) . . ?
N22 C27 S22 130.0(2) . . ?
C29 C28 N23 113.2(3) . . ?
C29 C28 H28 129.3(17) . . ?
N23 C28 H28 117.4(16) . . ?
C28 C29 S22 111.1(2) . . ?
C28 C29 H29 130(2) . . ?
S22 C29 H29 118(2) . . ?

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
O12 S11 N12 C17 -33.3(2) . . . . ?
O11 S11 N12 C17 -161.2(2) . . . . ?
C14 S11 N12 C17 84.9(2) . . . . ?
O22 S21 N22 C27 39.3(2) . . . . ?
O21 S21 N22 C27 167.0(2) . . . . ?
C24 S21 N22 C27 -78.9(2) . . . . ?
N11 C11 C12 C13 177.3(2) . . . . ?
C16 C11 C12 C13 -1.0(4) . . . . ?
C11 C12 C13 C14 -0.6(4) . . . . ?
C12 C13 C14 C15 1.0(4) . . . . ?
C12 C13 C14 S11 177.32(19) . . . . ?
O12 S11 C14 C15 9.0(2) . . . . ?
O11 S11 C14 C15 136.0(2) . . . . ?
N12 S11 C14 C15 -112.4(2) . . . . ?
O12 S11 C14 C13 -167.18(19) . . . . ?
O11 S11 C14 C13 -40.2(2) . . . . ?
N12 S11 C14 C13 71.4(2) . . . . ?
C13 C14 C15 C16 0.1(4) . . . . ?
S11 C14 C15 C16 -176.1(2) . . . . ?
C14 C15 C16 C11 -1.7(4) . . . . ?
N11 C11 C16 C15 -176.2(3) . . . . ?
C12 C11 C16 C15 2.2(4) . . . . ?
S11 N12 C17 N13 171.72(18) . . . . ?
S11 N12 C17 S12 -8.5(3) . . . . ?
C18 N13 C17 N12 -176.4(2) . . . . ?
C18 N13 C17 S12 3.8(3) . . . . ?
C19 S12 C17 N12 177.3(3) . . . . ?
C19 S12 C17 N13 -2.9(2) . . . . ?
C17 N13 C18 C19 -2.8(4) . . . . ?
N13 C18 C19 S12 0.4(3) . . . . ?
C17 S12 C19 C18 1.4(2) . . . . ?
N21 C21 C22 C23 177.7(2) . . . . ?
C26 C21 C22 C23 -1.3(4) . . . . ?
C21 C22 C23 C24 -1.1(4) . . . . ?
C22 C23 C24 C25 2.6(4) . . . . ?
C22 C23 C24 S21 -175.5(2) . . . . ?
O22 S21 C24 C23 162.1(2) . . . . ?
O21 S21 C24 C23 33.6(2) . . . . ?
N22 S21 C24 C23 -77.7(2) . . . . ?
O22 S21 C24 C25 -16.0(2) . . . . ?
O21 S21 C24 C25 -144.4(2) . . . . ?
N22 S21 C24 C25 104.2(2) . . . . ?
C23 C24 C25 C26 -1.7(4) . . . . ?
S21 C24 C25 C26 176.5(2) . . . . ?
C24 C25 C26 C21 -0.8(4) . . . . ?
N21 C21 C26 C25 -176.7(2) . . . . ?
C22 C21 C26 C25 2.2(4) . . . . ?
C28 N23 C27 N22 -175.7(2) . . . . ?
C28 N23 C27 S22 3.8(3) . . . . ?
S21 N22 C27 N23 178.61(19) . . . . ?
S21 N22 C27 S22 -0.8(4) . . . . ?
C29 S22 C27 N23 -3.5(2) . . . . ?
C29 S22 C27 N22 175.9(3) . . . . ?
C27 N23 C28 C29 -2.0(4) . . . . ?
N23 C28 C29 S22 -0.9(4) . . . . ?
C27 S22 C29 C28 2.5(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.03
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.315
_refine_diff_density_min         -0.475
_refine_diff_density_rms         0.077

data_SUTHAZ05_form_II_CSD
_database_code_depnum_ccdc_archive 'CCDC 137993'
_audit_creation_date             2000-01-11
_audit_creation_method           CSD-ConQuest-V1
_database_code_CSD               SUTHAZ05
_chemical_formula_sum            'C9 H9 N3 O2 S2'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 1/2+x,1/2-y,1/2+z
3 -x,-y,-z
4 -1/2-x,-1/2+y,-1/2-z
_cell_length_a                   10.399(2)
_cell_length_b                   15.132(3)
_cell_length_c                   14.280(3)
_cell_angle_alpha                90
_cell_angle_beta                 91.21(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
loop_
_atom_type_symbol
_atom_type_radius_bond
_atom_type_radius_vdwaals
C 0.68 1.7
H 0.23 1.2
O 0.68 1.7
S 1.02 2.1
N 0.68 1.55
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
S1 S 0.17581(7) 0.40001(6) -0.14444(6)
S2 S 0.33345(8) 0.37399(7) 0.05805(6)
O1 O 0.1372(2) 0.35111(16) -0.22744(16)
O2 O 0.11201(19) 0.37652(15) -0.05911(16)
N1 N 0.0924(3) 0.7823(2) -0.1961(3)
H1 H 0.129(3) 0.816(2) -0.240(2)
H2 H 0.036(4) 0.815(3) -0.159(3)
N2 N 0.3282(2) 0.38965(19) -0.13676(18)
N3 N 0.5198(2) 0.38573(18) -0.05178(19)
H3 H 0.56460 0.39120 -0.10140
C1 C 0.1098(3) 0.6944(2) -0.1880(2)
C2 C 0.2078(3) 0.6499(2) -0.2361(2)
H4 H 0.26010 0.68140 -0.27620
C3 C 0.2270(3) 0.5608(2) -0.2246(2)
H5 H 0.29180 0.53250 -0.25710
C4 C 0.1496(3) 0.5122(2) -0.1643(2)
C5 C 0.0505(3) 0.5555(2) -0.1180(2)
H6 H -0.00270 0.52380 -0.07870
C6 C 0.0312(3) 0.6450(2) -0.1301(2)
H7 H -0.03530 0.67270 -0.09910
C7 C 0.3906(3) 0.3844(2) -0.0549(2)
C8 C 0.5758(3) 0.3777(3) 0.0362(2)
H8 H 0.66420 0.37660 0.04750
C9 C 0.4893(3) 0.3716(3) 0.1032(3)
H9 H 0.50990 0.36670 0.16670
S3 S 0.17103(7) 0.05317(6) 0.17760(6)
S4 S 0.32040(8) 0.10341(8) -0.01384(6)
O3 O 0.0954(2) 0.09562(15) 0.10411(16)
O4 O 0.1264(2) 0.06537(17) 0.27229(16)
N4 N 0.1688(3) -0.3323(2) 0.1077(2)
H10 H 0.100(2) -0.356(2) 0.077(2)
H11 H 0.192(3) -0.366(2) 0.1568(18)
N5 N 0.3178(2) 0.08555(18) 0.18073(19)
N6 N 0.5033(3) 0.1230(2) 0.1031(2)
H12 H 0.54740 0.12670 0.15460
C10 C 0.1670(3) -0.2432(2) 0.1252(2)
C11 C 0.0845(3) -0.1869(2) 0.0750(2)
H13 H 0.02670 -0.21050 0.03120
C12 C 0.0873(3) -0.0971(2) 0.0894(2)
H14 H 0.03140 -0.06080 0.05520
C13 C 0.1724(3) -0.0601(2) 0.1542(2)
C14 C 0.2561(3) -0.1149(2) 0.2054(2)
H15 H 0.31340 -0.09060 0.24920
C15 C 0.2536(3) -0.2050(2) 0.1910(2)
H16 H 0.30980 -0.24110 0.22510
C16 C 0.3776(3) 0.1022(2) 0.1020(2)
C17 C 0.5577(4) 0.1382(3) 0.0176(3)
H17 H 0.64370 0.15280 0.00990
C18 C 0.4728(4) 0.1297(3) -0.0526(3)
H18 H 0.49260 0.13700 -0.11530

data_form_III
_database_code_depnum_ccdc_archive 'CCDC 687587'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H9 N3 O2 S2'
_chemical_formula_weight         255.31

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                   17.448(3)
_cell_length_b                   8.498(2)
_cell_length_c                   15.511(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 112.81(3)
_cell_angle_gamma                90.00
_cell_volume                     2120.0(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.600
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1056
_exptl_absorpt_coefficient_mu    0.489
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9085
_exptl_absorpt_correction_T_max  0.9302
_exptl_absorpt_process_details   'SADABS V2.10 (Sheldrick, 2003)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      150(2)
__diffrn_radiation_wavelength    0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker-Nonius 95mm CCD camera on κ-goniostat'
_diffrn_measurement_method       'φ & ω scans'
_diffrn_detector_area_resol_mean 9.091
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            17182
_diffrn_reflns_av_R_equivalents  0.1049
_diffrn_reflns_av_sigmaI/netI    0.0904
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.53
_diffrn_reflns_theta_max         25.03
_reflns_number_total             3723
_reflns_number_gt                2239
_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)+(0.0463P)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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3723
_refine_ls_number_parameters     361
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.1024
_refine_ls_R_factor_gt           0.0485
_refine_ls_wR_factor_ref         0.1072
_refine_ls_wR_factor_gt          0.0946
_refine_ls_goodness_of_fit_ref   0.930
_refine_ls_restrained_S_all      0.929
_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
S11 S 0.38389(6) 0.89999(10) 0.05813(5) 0.0224(2) Uani 1 1 d . . .
S12 S 0.35594(7) 0.67522(11) -0.12332(6) 0.0358(3) Uani 1 1 d . . .
O11 O 0.43201(15) 0.9805(3) 0.14457(14) 0.0265(6) Uani 1 1 d . . .
O12 O 0.37758(15) 0.9780(3) -0.02689(14) 0.0266(6) Uani 1 1 d . . .
N11 N 0.0429(2) 0.8058(3) 0.04887(19) 0.0229(7) Uani 1 1 d D . .
N12 N 0.42098(19) 0.7271(3) 0.06960(17) 0.0243(7) Uani 1 1 d . . .
N13 N 0.41198(18) 0.4768(3) 0.00738(18) 0.0226(7) Uani 1 1 d D . .
C11 C 0.1228(2) 0.8299(4) 0.0495(2) 0.0201(8) Uani 1 1 d . . .
C12 C 0.1921(2) 0.7666(4) 0.1219(2) 0.0217(9) Uani 1 1 d . . .
C13 C 0.2708(3) 0.7879(4) 0.1239(2) 0.0229(9) Uani 1 1 d . . .
C14 C 0.2825(2) 0.8755(4) 0.0544(2) 0.0202(8) Uani 1 1 d . . .
C15 C 0.2139(2) 0.9412(4) -0.0170(2) 0.0218(9) Uani 1 1 d . . .
C16 C 0.1357(2) 0.9194(4) -0.0190(2) 0.0195(8) Uani 1 1 d . . .
C17 C 0.3990(2) 0.6322(4) -0.0041(2) 0.0230(8) Uani 1 1 d . . .
C18 C 0.3886(3) 0.3902(5) -0.0737(2) 0.0296(9) Uani 1 1 d . . .
C19 C 0.3571(3) 0.4784(4) -0.1498(3) 0.0371(11) Uani 1 1 d . . .
S21 S 0.10697(6) 0.38054(10) 0.18198(5) 0.0227(2) Uani 1 1 d . . .
S22 S 0.13791(7) 0.14944(11) 0.36058(5) 0.0360(3) Uani 1 1 d . . .
O21 O 0.05793(15) 0.4621(3) 0.09711(14) 0.0283(6) Uani 1 1 d . . .
O22 O 0.11267(15) 0.4496(3) 0.26910(14) 0.0264(6) Uani 1 1 d . . .
N21 N 0.4468(2) 0.3251(4) 0.18213(19) 0.0249(7) Uani 1 1 d D . .
N22 N 0.07236(18) 0.2041(3) 0.16818(16) 0.0215(7) Uani 1 1 d . . .
N23 N 0.08016(19) -0.0471(3) 0.22929(17) 0.0228(7) Uani 1 1 d D . .
C21 C 0.3679(2) 0.3390(4) 0.1853(2) 0.0200(8) Uani 1 1 d . . .
C22 C 0.2995(3) 0.2777(4) 0.1113(2) 0.0241(9) Uani 1 1 d . . .
C23 C 0.2210(3) 0.2898(4) 0.1116(2) 0.0252(9) Uani 1 1 d . . .
C24 C 0.2085(2) 0.3648(4) 0.1857(2) 0.0202(8) Uani 1 1 d . . .
C25 C 0.2768(2) 0.4266(4) 0.2589(2) 0.0225(9) Uani 1 1 d . . .
C26 C 0.3556(2) 0.4148(4) 0.2586(2) 0.0226(9) Uani 1 1 d . . .
C27 C 0.0934(2) 0.1072(4) 0.2418(2) 0.0227(8) Uani 1 1 d . . .
C28 C 0.1057(2) -0.1349(4) 0.3107(2) 0.0302(10) Uani 1 1 d . . .
C29 C 0.1377(3) -0.0492(4) 0.3866(3) 0.0384(11) Uani 1 1 d . . .
H10 H 0.0052(19) 0.821(4) -0.0079(15) 0.039(12) Uiso 1 1 d D . .
H11 H 0.038(2) 0.707(2) 0.064(2) 0.038(11) Uiso 1 1 d D . .
H12 H 0.1815(19) 0.709(3) 0.1685(19) 0.016(8) Uiso 1 1 d . . .
H13 H 0.314(2) 0.741(3) 0.1720(19) 0.011(8) Uiso 1 1 d . . .
H15 H 0.226(2) 1.001(4) -0.061(2) 0.027(9) Uiso 1 1 d . . .
H16 H 0.087(2) 0.961(3) -0.070(2) 0.021(9) Uiso 1 1 d . . .
H17 H 0.431(2) 0.435(4) 0.0640(14) 0.027(10) Uiso 1 1 d D . .
H18 H 0.397(2) 0.284(4) -0.067(2) 0.027(10) Uiso 1 1 d . . .
H19 H 0.340(2) 0.450(4) -0.209(2) 0.042(12) Uiso 1 1 d . . .
H20 H 0.4873(18) 0.360(4) 0.2329(17) 0.043(12) Uiso 1 1 d D . .
H21 H 0.456(2) 0.232(2) 0.1679(19) 0.017(9) Uiso 1 1 d D . .
H22 H 0.309(2) 0.225(4) 0.058(2) 0.044(11) Uiso 1 1 d . . .
H23 H 0.173(2) 0.244(4) 0.066(2) 0.019(9) Uiso 1 1 d . . .
H25 H 0.270(2) 0.482(4) 0.310(2) 0.023(9) Uiso 1 1 d . . .
H26 H 0.403(2) 0.447(4) 0.312(2) 0.026(9) Uiso 1 1 d . . .
H27 H 0.063(3) -0.088(4) 0.1721(16) 0.059(13) Uiso 1 1 d D . .
H28 H 0.097(2) -0.241(4) 0.301(2) 0.027(10) Uiso 1 1 d . . .
H29 H 0.161(2) -0.073(4) 0.451(2) 0.039(11) 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
S11 O12 1.442(2) . ?
S11 O11 1.448(2) . ?
S11 N12 1.588(3) . ?
S11 C14 1.760(4) . ?
S12 C19 1.725(4) . ?
S12 C17 1.744(3) . ?
N11 C11 1.406(4) . ?
N11 H10 0.881(18) . ?
N11 H11 0.887(18) . ?
N12 C17 1.328(4) . ?
N13 C17 1.340(4) . ?
N13 C18 1.376(4) . ?
N13 H17 0.884(17) . ?
C11 C16 1.393(4) . ?
C11 C12 1.401(5) . ?
C12 C13 1.374(5) . ?
C12 H12 0.95(3) . ?
C13 C14 1.388(4) . ?
C13 H13 0.92(3) . ?
C14 C15 1.395(5) . ?
C15 C16 1.365(5) . ?
C15 H15 0.94(3) . ?
C16 H16 0.97(3) . ?
C18 C19 1.324(5) . ?
C18 H18 0.92(3) . ?
C19 H19 0.89(3) . ?
S21 O21 1.440(2) . ?
S21 O22 1.441(2) . ?
S21 N22 1.600(3) . ?
S21 C24 1.755(4) . ?
S22 C29 1.736(4) . ?
S22 C27 1.736(3) . ?
N21 C21 1.401(5) . ?
N21 H20 0.880(18) . ?
N21 H21 0.854(18) . ?
N22 C27 1.339(4) . ?
N23 C27 1.333(4) . ?
N23 C28 1.384(4) . ?
N23 H27 0.888(18) . ?
C21 C26 1.395(4) . ?
C21 C22 1.396(5) . ?
C22 C23 1.376(5) . ?
C22 H22 1.01(3) . ?
C23 C24 1.404(4) . ?
C23 H23 0.94(3) . ?
C24 C25 1.392(5) . ?
C25 C26 1.381(5) . ?
C25 H25 0.97(3) . ?
C26 H26 0.96(3) . ?
C28 C29 1.310(5) . ?
C28 H28 0.92(3) . ?
C29 H29 0.94(3) . ?

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
O12 S11 O11 116.16(14) . . ?
O12 S11 N12 114.29(14) . . ?
O11 S11 N12 105.58(14) . . ?
O12 S11 C14 107.78(15) . . ?
O11 S11 C14 107.50(14) . . ?
N12 S11 C14 104.78(16) . . ?
C19 S12 C17 90.50(18) . . ?
C11 N11 H10 110(2) . . ?
C11 N11 H11 110(3) . . ?
H10 N11 H11 108(3) . . ?
C17 N12 S11 119.8(2) . . ?
C17 N13 C18 115.5(3) . . ?
C17 N13 H17 120(2) . . ?
C18 N13 H17 124(2) . . ?
C16 C11 C12 118.4(4) . . ?
C16 C11 N11 121.9(3) . . ?
C12 C11 N11 119.7(3) . . ?
C13 C12 C11 120.8(3) . . ?
C13 C12 H12 122.7(19) . . ?
C11 C12 H12 117(2) . . ?
C12 C13 C14 120.0(3) . . ?
C12 C13 H13 117.4(19) . . ?
C14 C13 H13 122.6(19) . . ?
C13 C14 C15 119.5(3) . . ?
C13 C14 S11 119.1(3) . . ?
C15 C14 S11 121.4(3) . . ?
C16 C15 C14 120.4(3) . . ?
C16 C15 H15 124(2) . . ?
C14 C15 H15 116(2) . . ?
C15 C16 C11 120.8(3) . . ?
C15 C16 H16 121.3(19) . . ?
C11 C16 H16 117.8(19) . . ?
N12 C17 N13 120.4(3) . . ?
N12 C17 S12 130.3(3) . . ?
N13 C17 S12 109.2(2) . . ?
C19 C18 N13 112.7(4) . . ?
C19 C18 H18 131(2) . . ?
N13 C18 H18 117(2) . . ?
C18 C19 S12 112.1(3) . . ?
C18 C19 H19 129(2) . . ?
S12 C19 H19 119(2) . . ?
O21 S21 O22 117.51(14) . . ?
O21 S21 N22 105.62(14) . . ?
O22 S21 N22 113.13(14) . . ?
O21 S21 C24 107.53(14) . . ?
O22 S21 C24 107.36(15) . . ?
N22 S21 C24 104.88(15) . . ?
C29 S22 C27 90.30(17) . . ?
C21 N21 H20 114(2) . . ?
C21 N21 H21 112(2) . . ?
H20 N21 H21 112(3) . . ?
C27 N22 S21 119.8(2) . . ?
C27 N23 C28 114.9(3) . . ?
C27 N23 H27 120(3) . . ?
C28 N23 H27 125(3) . . ?
C26 C21 C22 119.3(4) . . ?
C26 C21 N21 122.1(3) . . ?
C22 C21 N21 118.6(3) . . ?
C23 C22 C21 120.4(3) . . ?
C23 C22 H22 121(2) . . ?
C21 C22 H22 118(2) . . ?
C22 C23 C24 120.5(4) . . ?
C22 C23 H23 124(2) . . ?
C24 C23 H23 116(2) . . ?
C25 C24 C23 119.0(3) . . ?
C25 C24 S21 122.1(3) . . ?
C23 C24 S21 118.9(3) . . ?
C26 C25 C24 120.5(3) . . ?
C26 C25 H25 119(2) . . ?
C24 C25 H25 121(2) . . ?
C25 C26 C21 120.4(3) . . ?
C25 C26 H26 121(2) . . ?
C21 C26 H26 119(2) . . ?
N23 C27 N22 120.4(3) . . ?
N23 C27 S22 109.8(2) . . ?
N22 C27 S22 129.8(3) . . ?
C29 C28 N23 113.2(3) . . ?
C29 C28 H28 133(2) . . ?
N23 C28 H28 114(2) . . ?
C28 C29 S22 111.7(3) . . ?
C28 C29 H29 133(2) . . ?
S22 C29 H29 115(2) . . ?

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
O12 S11 N12 C17 -39.9(3) . . . . ?
O11 S11 N12 C17 -168.8(3) . . . . ?
C14 S11 N12 C17 77.8(3) . . . . ?
C16 C11 C12 C13 -2.0(5) . . . . ?
N11 C11 C12 C13 179.7(3) . . . . ?
C11 C12 C13 C14 1.2(5) . . . . ?
C12 C13 C14 C15 0.0(5) . . . . ?
C12 C13 C14 S11 -179.6(2) . . . . ?
O12 S11 C14 C13 173.1(2) . . . . ?
O11 S11 C14 C13 -61.0(3) . . . . ?
N12 S11 C14 C13 51.0(3) . . . . ?
O12 S11 C14 C15 -6.4(3) . . . . ?
O11 S11 C14 C15 119.5(3) . . . . ?
N12 S11 C14 C15 -128.5(3) . . . . ?
C13 C14 C15 C16 -0.2(5) . . . . ?
S11 C14 C15 C16 179.4(2) . . . . ?
C14 C15 C16 C11 -0.8(5) . . . . ?
C12 C11 C16 C15 1.8(5) . . . . ?
N11 C11 C16 C15 -180.0(3) . . . . ?
S11 N12 C17 N13 -163.1(3) . . . . ?
S11 N12 C17 S12 19.5(5) . . . . ?
C18 N13 C17 N12 -178.6(3) . . . . ?
C18 N13 C17 S12 -0.7(4) . . . . ?
C19 S12 C17 N12 178.4(4) . . . . ?
C19 S12 C17 N13 0.7(3) . . . . ?
C17 N13 C18 C19 0.2(5) . . . . ?
N13 C18 C19 S12 0.4(5) . . . . ?
C17 S12 C19 C18 -0.6(4) . . . . ?
O21 S21 N22 C27 -166.3(3) . . . . ?
O22 S21 N22 C27 -36.4(3) . . . . ?
C24 S21 N22 C27 80.2(3) . . . . ?
C26 C21 C22 C23 -1.0(5) . . . . ?
N21 C21 C22 C23 -179.6(3) . . . . ?
C21 C22 C23 C24 0.4(5) . . . . ?
C22 C23 C24 C25 0.0(5) . . . . ?
C22 C23 C24 S21 178.9(3) . . . . ?
O21 S21 C24 C25 121.5(3) . . . . ?
O22 S21 C24 C25 -5.8(3) . . . . ?
N22 S21 C24 C25 -126.4(3) . . . . ?
O21 S21 C24 C23 -57.4(3) . . . . ?
O22 S21 C24 C23 175.3(2) . . . . ?
N22 S21 C24 C23 54.7(3) . . . . ?
C23 C24 C25 C26 0.2(5) . . . . ?
S21 C24 C25 C26 -178.7(2) . . . . ?
C24 C25 C26 C21 -0.7(5) . . . . ?
C22 C21 C26 C25 1.2(5) . . . . ?
N21 C21 C26 C25 179.7(3) . . . . ?
C28 N23 C27 N22 179.1(3) . . . . ?
C28 N23 C27 S22 -1.3(4) . . . . ?
S21 N22 C27 N23 -165.8(3) . . . . ?
S21 N22 C27 S22 14.7(5) . . . . ?
C29 S22 C27 N23 1.1(3) . . . . ?
C29 S22 C27 N22 -179.3(4) . . . . ?
C27 N23 C28 C29 0.9(5) . . . . ?
N23 C28 C29 S22 0.0(5) . . . . ?
C27 S22 C29 C28 -0.6(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N11 H10 N22 0.881(18) 2.33(2) 3.184(4) 162(3) 3_565
N11 H11 O21 0.887(18) 2.14(2) 3.001(4) 164(3) .
N13 H17 N21 0.884(17) 1.978(19) 2.846(4) 167(3) .
N21 H20 O11 0.880(18) 2.14(2) 3.005(4) 168(3) 2_645
N21 H21 O11 0.854(18) 2.18(2) 2.977(4) 155(3) 1_545
N23 H27 N11 0.888(18) 2.02(2) 2.899(4) 171(4) 1_545

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        25.03
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.434
_refine_diff_density_min         -0.479
_refine_diff_density_rms         0.077

data_form_IV
_database_code_depnum_ccdc_archive 'CCDC 687588'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H9 N3 O2 S2'
_chemical_formula_weight         255.31

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                   8.193(2)
_cell_length_b                   8.538(2)
_cell_length_c                   15.437(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.01(3)
_cell_angle_gamma                90.00
_cell_volume                     1077.2(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.574
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             528
_exptl_absorpt_coefficient_mu    0.482
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9098
_exptl_absorpt_correction_T_max  0.9313
_exptl_absorpt_process_details   'SADABS V2.10 (Sheldrick, 2003)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker-Nonius 95mm CCD camera on κ-goniostat'
_diffrn_measurement_method       'φ & ω scans'
_diffrn_detector_area_resol_mean 9.091
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10998
_diffrn_reflns_av_R_equivalents  0.0341
_diffrn_reflns_av_sigmaI/netI    0.0259
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.49
_diffrn_reflns_theta_max         25.02
_reflns_number_total             1893
_reflns_number_gt                1771
_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)+(0.0450P)²+0.7248P] 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         1893
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0335
_refine_ls_R_factor_gt           0.0310
_refine_ls_wR_factor_ref         0.0827
_refine_ls_wR_factor_gt          0.0812
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_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
S11 S 0.72911(5) 0.10805(5) 0.61714(3) 0.01635(15) Uani 1 1 d . . .
S12 S 0.78781(7) 0.33354(6) 0.45120(3) 0.02974(17) Uani 1 1 d . . .
O11 O 0.63364(15) 0.02699(14) 0.67837(8) 0.0218(3) Uani 1 1 d . . .
O12 O 0.74220(15) 0.03243(15) 0.53434(8) 0.0226(3) Uani 1 1 d . . .
N11 N 1.39656(19) 0.18311(19) 0.79035(10) 0.0196(3) Uani 1 1 d . . .
N12 N 0.65663(18) 0.28125(17) 0.61053(9) 0.0189(3) Uani 1 1 d . . .
N13 N 0.67330(18) 0.53000(17) 0.55278(10) 0.0189(3) Uani 1 1 d . . .
C11 C 1.2409(2) 0.16591(18) 0.74689(11) 0.0164(4) Uani 1 1 d . . .
C12 C 1.1046(2) 0.2289(2) 0.78418(11) 0.0189(4) Uani 1 1 d . . .
C13 C 0.9500(2) 0.2127(2) 0.74370(11) 0.0186(4) Uani 1 1 d . . .
C14 C 0.9288(2) 0.12985(19) 0.66592(11) 0.0161(4) Uani 1 1 d . . .
C15 C 1.0627(2) 0.0658(2) 0.62891(11) 0.0169(4) Uani 1 1 d . . .
C16 C 1.2185(2) 0.0828(2) 0.66907(11) 0.0173(4) Uani 1 1 d . . .
C17 C 0.6999(2) 0.3757(2) 0.54814(11) 0.0175(4) Uani 1 1 d . . .
C18 C 0.7213(2) 0.6171(2) 0.48362(12) 0.0256(4) Uani 1 1 d . . .
C19 C 0.7855(3) 0.5308(2) 0.42364(14) 0.0341(5) Uani 1 1 d . . .
H10 H 1.477(3) 0.153(3) 0.7580(15) 0.029(6) Uiso 1 1 d . . .
H11 H 1.411(3) 0.276(3) 0.8087(14) 0.026(6) Uiso 1 1 d . . .
H12 H 1.120(3) 0.284(3) 0.8371(14) 0.026(5) Uiso 1 1 d . . .
H13 H 0.858(3) 0.255(2) 0.7688(13) 0.020(5) Uiso 1 1 d . . .
H15 H 1.049(2) 0.011(2) 0.5790(14) 0.020(5) Uiso 1 1 d . . .
H16 H 1.307(3) 0.044(2) 0.6408(12) 0.018(5) Uiso 1 1 d . . .
H17 H 0.635(3) 0.571(3) 0.6000(15) 0.031(6) Uiso 1 1 d . . .
H18 H 0.705(3) 0.725(3) 0.4850(14) 0.031(6) Uiso 1 1 d . . .
H19 H 0.826(3) 0.559(3) 0.3727(17) 0.042(7) 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
S11 O12 1.4427(13) . ?
S11 O11 1.4448(13) . ?
S11 N12 1.5941(15) . ?
S11 C14 1.7625(18) . ?
S12 C19 1.737(2) . ?
S12 C17 1.7431(18) . ?
N11 C11 1.407(2) . ?
N12 C17 1.323(2) . ?
N13 C17 1.338(2) . ?
N13 C18 1.381(2) . ?
C11 C16 1.396(2) . ?
C11 C12 1.399(3) . ?
C12 C13 1.379(3) . ?
C13 C14 1.394(2) . ?
C14 C15 1.385(3) . ?
C15 C16 1.386(3) . ?
C18 C19 1.321(3) . ?

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
O12 S11 O11 116.26(8) . . ?
O12 S11 N12 114.14(8) . . ?
O11 S11 N12 105.66(8) . . ?
O12 S11 C14 107.55(8) . . ?
O11 S11 C14 107.45(8) . . ?
N12 S11 C14 105.06(8) . . ?
C19 S12 C17 90.70(9) . . ?
C17 N12 S11 119.62(13) . . ?
C17 N13 C18 115.64(16) . . ?
C16 C11 C12 119.23(16) . . ?
C16 C11 N11 121.59(16) . . ?
C12 C11 N11 119.14(16) . . ?
C13 C12 C11 120.61(16) . . ?
C12 C13 C14 119.75(16) . . ?
C15 C14 C13 120.08(16) . . ?
C15 C14 S11 121.38(14) . . ?
C13 C14 S11 118.54(14) . . ?
C14 C15 C16 120.33(17) . . ?
C15 C16 C11 119.98(17) . . ?
N12 C17 N13 120.53(16) . . ?
N12 C17 S12 130.32(14) . . ?
N13 C17 S12 109.12(13) . . ?
C19 C18 N13 112.98(18) . . ?
C18 C19 S12 111.56(16) . . ?

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
O12 S11 N12 C17 -39.22(16) . . . . ?
O11 S11 N12 C17 -168.20(13) . . . . ?
C14 S11 N12 C17 78.35(15) . . . . ?
C16 C11 C12 C13 -1.6(3) . . . . ?
N11 C11 C12 C13 -179.34(16) . . . . ?
C11 C12 C13 C14 1.5(3) . . . . ?
C12 C13 C14 C15 -0.8(3) . . . . ?
C12 C13 C14 S11 178.72(13) . . . . ?
O12 S11 C14 C15 -6.00(16) . . . . ?
O11 S11 C14 C15 119.85(15) . . . . ?
N12 S11 C14 C15 -127.96(14) . . . . ?
O12 S11 C14 C13 174.47(13) . . . . ?
O11 S11 C14 C13 -59.68(15) . . . . ?
N12 S11 C14 C13 52.51(15) . . . . ?
C13 C14 C15 C16 0.3(3) . . . . ?
S11 C14 C15 C16 -179.18(13) . . . . ?
C14 C15 C16 C11 -0.5(3) . . . . ?
C12 C11 C16 C15 1.1(2) . . . . ?
N11 C11 C16 C15 178.79(15) . . . . ?
S11 N12 C17 N13 -164.09(13) . . . . ?
S11 N12 C17 S12 17.9(2) . . . . ?
C18 N13 C17 N12 -179.19(16) . . . . ?
C18 N13 C17 S12 -0.82(19) . . . . ?
C19 S12 C17 N12 178.96(18) . . . . ?
C19 S12 C17 N13 0.80(14) . . . . ?
C17 N13 C18 C19 0.4(3) . . . . ?
N13 C18 C19 S12 0.3(2) . . . . ?
C17 S12 C19 C18 -0.63(18) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N11 H10 O11 0.89(2) 2.13(3) 3.001(2) 165(2) 1_655
N11 H11 O11 0.85(2) 2.19(2) 2.989(2) 157.8(19) 2_756
N13 H17 N11 0.89(2) 1.98(2) 2.845(2) 166(2) 2_756

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.479
_refine_diff_density_rms         0.056

data_form_V
_database_code_depnum_ccdc_archive 'CCDC 687589'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H9 N3 O2 S2'
_chemical_formula_weight         255.31

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/n

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

_cell_length_a                   10.7740(10)
_cell_length_b                   8.4670(10)
_cell_length_c                   11.3670(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.650(10)
_cell_angle_gamma                90.00
_cell_volume                     1036.51(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.636
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             528
_exptl_absorpt_coefficient_mu    0.500
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8851
_exptl_absorpt_correction_T_max  0.9706
_exptl_absorpt_process_details   'SADABS V2.10 (Sheldrick, 2003)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker-Nonius 95mm CCD camera on κ-goniostat'
_diffrn_measurement_method       'φ & ω scans'
_diffrn_detector_area_resol_mean 9.091
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7262
_diffrn_reflns_av_R_equivalents  0.0756
_diffrn_reflns_av_sigmaI/netI    0.0643
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.00
_diffrn_reflns_theta_max         26.00
_reflns_number_total             2026
_reflns_number_gt                1655
_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)+(0.0515P)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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2026
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0555
_refine_ls_R_factor_gt           0.0382
_refine_ls_wR_factor_ref         0.0959
_refine_ls_wR_factor_gt          0.0910
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_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
S11 S 0.48228(5) 0.11472(6) 0.26293(4) 0.01403(18) Uani 1 1 d . . .
S12 S 0.34389(6) 0.34250(6) 0.06718(5) 0.02392(19) Uani 1 1 d . . .
O11 O 0.49723(14) 0.03463(15) 0.37404(12) 0.0190(4) Uani 1 1 d . . .
O12 O 0.40188(14) 0.04220(15) 0.17448(12) 0.0181(4) Uani 1 1 d . . .
N11 N 0.98740(17) 0.1901(2) 0.07072(16) 0.0163(4) Uani 1 1 d . . .
N12 N 0.44221(16) 0.29157(19) 0.29397(14) 0.0146(4) Uani 1 1 d . . .
N13 N 0.38859(17) 0.54216(19) 0.22789(15) 0.0144(4) Uani 1 1 d . . .
C11 C 0.8672(2) 0.1691(2) 0.11378(17) 0.0135(4) Uani 1 1 d . . .
C12 C 0.8393(2) 0.2310(2) 0.22415(18) 0.0152(5) Uani 1 1 d . . .
C13 C 0.7221(2) 0.2152(2) 0.26780(17) 0.0144(5) Uani 1 1 d . . .
C14 C 0.63056(19) 0.1339(2) 0.20310(17) 0.0134(4) Uani 1 1 d . . .
C15 C 0.6582(2) 0.0682(2) 0.09514(17) 0.0141(4) Uani 1 1 d . . .
C16 C 0.7761(2) 0.0845(2) 0.05115(17) 0.0137(4) Uani 1 1 d . . .
C17 C 0.39804(19) 0.3863(2) 0.20909(17) 0.0145(4) Uani 1 1 d . . .
C18 C 0.3421(2) 0.6287(3) 0.13377(19) 0.0188(5) Uani 1 1 d . . .
C19 C 0.3143(2) 0.5414(3) 0.0404(2) 0.0270(6) Uani 1 1 d . . .
H10 H 0.989(2) 0.164(3) -0.005(2) 0.027(7) Uiso 1 1 d . . .
H11 H 1.010(2) 0.283(3) 0.082(2) 0.027(7) Uiso 1 1 d . . .
H12 H 0.900(2) 0.289(3) 0.2670(19) 0.017(6) Uiso 1 1 d . . .
H13 H 0.704(2) 0.263(2) 0.346(2) 0.016(5) Uiso 1 1 d . . .
H15 H 0.595(2) 0.013(3) 0.053(2) 0.024(6) Uiso 1 1 d . . .
H16 H 0.794(2) 0.038(2) -0.0242(19) 0.012(5) Uiso 1 1 d . . .
H17 H 0.4147(19) 0.581(2) 0.2943(18) 0.008(5) Uiso 1 1 d . . .
H18 H 0.337(2) 0.740(3) 0.144(2) 0.028(6) Uiso 1 1 d . . .
H19 H 0.290(2) 0.562(3) -0.032(2) 0.032(7) 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
S11 O11 1.4384(14) . ?
S11 O12 1.4449(14) . ?
S11 N12 1.6006(17) . ?
S11 C14 1.762(2) . ?
S12 C19 1.739(2) . ?
S12 C17 1.740(2) . ?
N11 C11 1.409(3) . ?
N11 H10 0.89(3) . ?
N11 H11 0.84(3) . ?
N12 C17 1.332(3) . ?
N13 C17 1.341(3) . ?
N13 C18 1.379(3) . ?
N13 H17 0.86(2) . ?
C11 C16 1.394(3) . ?
C11 C12 1.400(3) . ?
C12 C13 1.376(3) . ?
C12 H12 0.94(2) . ?
C13 C14 1.395(3) . ?
C13 H13 1.00(2) . ?
C14 C15 1.387(3) . ?
C15 C16 1.385(3) . ?
C15 H15 0.95(2) . ?
C16 H16 0.97(2) . ?
C18 C19 1.321(3) . ?
C18 H18 0.95(3) . ?
C19 H19 0.88(3) . ?

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
O11 S11 O12 117.41(9) . . ?
O11 S11 N12 105.76(9) . . ?
O12 S11 N12 113.01(9) . . ?
O11 S11 C14 107.60(9) . . ?
O12 S11 C14 107.62(9) . . ?
N12 S11 C14 104.61(9) . . ?
C19 S12 C17 90.61(11) . . ?
C11 N11 H10 110.6(17) . . ?
C11 N11 H11 109.6(17) . . ?
H10 N11 H11 112(2) . . ?
C17 N12 S11 119.79(14) . . ?
C17 N13 C18 115.27(18) . . ?
C17 N13 H17 119.4(13) . . ?
C18 N13 H17 125.3(13) . . ?
C16 C11 C12 118.9(2) . . ?
C16 C11 N11 121.88(19) . . ?
C12 C11 N11 119.18(19) . . ?
C13 C12 C11 120.6(2) . . ?
C13 C12 H12 119.7(14) . . ?
C11 C12 H12 119.6(14) . . ?
C12 C13 C14 119.99(19) . . ?
C12 C13 H13 118.8(13) . . ?
C14 C13 H13 121.2(13) . . ?
C15 C14 C13 119.9(2) . . ?
C15 C14 S11 121.63(16) . . ?
C13 C14 S11 118.50(15) . . ?
C16 C15 C14 120.1(2) . . ?
C16 C15 H15 121.6(14) . . ?
C14 C15 H15 118.3(14) . . ?
C15 C16 C11 120.43(19) . . ?
C15 C16 H16 119.1(13) . . ?
C11 C16 H16 120.5(13) . . ?
N12 C17 N13 120.29(17) . . ?
N12 C17 S12 130.27(15) . . ?
N13 C17 S12 109.43(15) . . ?
C19 C18 N13 113.2(2) . . ?
C19 C18 H18 129.5(14) . . ?
N13 C18 H18 117.3(14) . . ?
C18 C19 S12 111.44(18) . . ?
C18 C19 H19 134.4(16) . . ?
S12 C19 H19 114.0(16) . . ?

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
O11 S11 N12 C17 -166.91(16) . . . . ?
O12 S11 N12 C17 -37.16(19) . . . . ?
C14 S11 N12 C17 79.62(18) . . . . ?
C16 C11 C12 C13 -3.1(3) . . . . ?
N11 C11 C12 C13 178.76(17) . . . . ?
C11 C12 C13 C14 1.4(3) . . . . ?
C12 C13 C14 C15 0.4(3) . . . . ?
C12 C13 C14 S11 179.36(15) . . . . ?
O11 S11 C14 C15 120.15(17) . . . . ?
O12 S11 C14 C15 -7.25(19) . . . . ?
N12 S11 C14 C15 -127.69(16) . . . . ?
O11 S11 C14 C13 -58.79(16) . . . . ?
O12 S11 C14 C13 173.80(14) . . . . ?
N12 S11 C14 C13 53.37(17) . . . . ?
C13 C14 C15 C16 -0.6(3) . . . . ?
S11 C14 C15 C16 -179.49(14) . . . . ?
C14 C15 C16 C11 -1.1(3) . . . . ?
C12 C11 C16 C15 2.9(3) . . . . ?
N11 C11 C16 C15 -178.98(17) . . . . ?
S11 N12 C17 N13 -166.05(16) . . . . ?
S11 N12 C17 S12 15.0(3) . . . . ?
C18 N13 C17 N12 179.78(19) . . . . ?
C18 N13 C17 S12 -1.0(2) . . . . ?
C19 S12 C17 N12 -179.7(2) . . . . ?
C19 S12 C17 N13 1.20(17) . . . . ?
C17 N13 C18 C19 0.2(3) . . . . ?
N13 C18 C19 S12 0.8(3) . . . . ?
C17 S12 C19 C18 -1.1(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N11 H10 N12 0.89(3) 2.36(3) 3.173(2) 153(2) 4_665
N11 H11 O11 0.84(3) 2.19(3) 2.988(2) 160(2) 2_655
N13 H17 N11 0.86(2) 2.06(2) 2.902(3) 166.3(19) 2_655

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.430
_refine_diff_density_min         -0.591
_refine_diff_density_rms         0.111


