# Electronic Supplementary Material for CrystEngComm
# This journal is (c) The Royal Society of Chemistry 2009

data_global

_journal_coden_Cambridge         1350

loop_
_publ_author_name
'Edward R.T. Tiekink'
'Carol A Ellis'
'Michael A. Miller'
'James Spencer'
'Julio Zukerman-Schpector'

_publ_contact_author_name        'Edward R.T. Tiekink'
_publ_contact_author_email       EDWARD.TIEKINK@UTSA.EDU

_publ_section_title              
;
Co-crystallization experiments of thiocarbamides with
bipyridine-type molecules
;

# Attachment '1.CIF'

data_shelxl
_database_code_depnum_ccdc_archive 'CCDC 713701'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H10 N2, 2(C8 H9 N O S)'
_chemical_formula_sum            'C28 H28 N4 O2 S2'
_chemical_formula_weight         516.66

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

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

_cell_length_a                   7.9582(15)
_cell_length_b                   9.2167(15)
_cell_length_c                   9.6845(19)
_cell_angle_alpha                73.672(9)
_cell_angle_beta                 81.868(11)
_cell_angle_gamma                70.650(9)
_cell_volume                     642.3(2)
_cell_formula_units_Z            1
_cell_measurement_temperature    98(2)
_cell_measurement_reflns_used    2298
_cell_measurement_theta_min      2.4
_cell_measurement_theta_max      40.5

_exptl_crystal_description       wedge
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             272
_exptl_absorpt_coefficient_mu    0.241
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.782
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_process_details   'ABSCOR (Higashi, 1995)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      98(2)
_diffrn_radiation_wavelength     0.71070
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  AFC12\k/SATURN724
_diffrn_measurement_method       \w
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        '< 1'
_diffrn_reflns_number            4560
_diffrn_reflns_av_R_equivalents  0.022
_diffrn_reflns_av_sigmaI/netI    0.033
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.2
_diffrn_reflns_theta_max         27.5
_reflns_number_total             2927
_reflns_number_gt                2695
_reflns_threshold_expression     I>2\s(I)

_computing_data_collection       'CrystalClear (Rigaku, 2005)'
_computing_cell_refinement       CrystalClear
_computing_data_reduction        CrystalClear
_computing_structure_solution    'SIR-92 (Altomare et al., 1994)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  SHELXL97

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0432P)^2^+0.3824P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2927
_refine_ls_number_parameters     164
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.050
_refine_ls_R_factor_gt           0.045
_refine_ls_wR_factor_ref         0.107
_refine_ls_wR_factor_gt          0.104
_refine_ls_goodness_of_fit_ref   1.08
_refine_ls_restrained_S_all      1.08
_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 0.33955(6) 1.36843(5) 0.13710(4) 0.02588(13) Uani 1 1 d . . .
O1 O 0.32027(15) 1.45848(14) -0.14915(13) 0.0252(3) Uani 1 1 d . . .
N1 N 0.54077(18) 1.23896(16) -0.06445(14) 0.0213(3) Uani 1 1 d . . .
H1N H 0.5940 1.1669 0.0103 0.026 Uiso 1 1 calc R . .
N2 N 0.75042(19) 0.98293(16) 0.16113(15) 0.0243(3) Uani 1 1 d . . .
C1 C 0.4027(2) 1.35711(18) -0.03299(17) 0.0206(3) Uani 1 1 d . . .
C2 C 0.6141(2) 1.21291(19) -0.20136(17) 0.0200(3) Uani 1 1 d . . .
C3 C 0.6136(2) 1.33389(19) -0.32587(17) 0.0223(3) Uani 1 1 d . . .
H3 H 0.5584 1.4418 -0.3237 0.027 Uiso 1 1 calc R . .
C4 C 0.6944(2) 1.2958(2) -0.45328(18) 0.0249(3) Uani 1 1 d . . .
H4 H 0.6917 1.3782 -0.5387 0.030 Uiso 1 1 calc R . .
C5 C 0.7791(2) 1.1388(2) -0.45723(18) 0.0258(4) Uani 1 1 d . . .
H5 H 0.8349 1.1140 -0.5447 0.031 Uiso 1 1 calc R . .
C6 C 0.7820(2) 1.0181(2) -0.33257(19) 0.0251(3) Uani 1 1 d . . .
H6 H 0.8409 0.9106 -0.3345 0.030 Uiso 1 1 calc R . .
C7 C 0.6987(2) 1.05463(19) -0.20532(18) 0.0228(3) Uani 1 1 d . . .
H7 H 0.6992 0.9718 -0.1206 0.027 Uiso 1 1 calc R . .
C8 C 0.1814(2) 1.6013(2) -0.1329(2) 0.0304(4) Uani 1 1 d . . .
H8A H 0.0887 1.5731 -0.0626 0.046 Uiso 1 1 calc R . .
H8B H 0.1291 1.6599 -0.2259 0.046 Uiso 1 1 calc R . .
H8C H 0.2320 1.6679 -0.0990 0.046 Uiso 1 1 calc R . .
C9 C 0.8912(2) 0.8595(2) 0.13976(18) 0.0243(3) Uani 1 1 d . . .
H9 H 0.9504 0.8686 0.0468 0.029 Uiso 1 1 calc R . .
C10 C 0.9552(2) 0.72067(19) 0.24430(17) 0.0224(3) Uani 1 1 d . . .
H10 H 1.0547 0.6373 0.2227 0.027 Uiso 1 1 calc R . .
C11 C 0.8713(2) 0.70440(18) 0.38262(17) 0.0197(3) Uani 1 1 d . . .
C12 C 0.7252(2) 0.83150(19) 0.40520(17) 0.0221(3) Uani 1 1 d . . .
H12 H 0.6628 0.8255 0.4968 0.026 Uiso 1 1 calc R . .
C13 C 0.6709(2) 0.96696(19) 0.29362(18) 0.0235(3) Uani 1 1 d . . .
H13 H 0.5723 1.0527 0.3122 0.028 Uiso 1 1 calc R . .
C14 C 0.9290(2) 0.56320(19) 0.50213(17) 0.0218(3) Uani 1 1 d . . .
H14 H 0.8591 0.5617 0.5903 0.026 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 0.0280(2) 0.0230(2) 0.0211(2) -0.00520(15) 0.00532(16) -0.00360(16)
O1 0.0218(6) 0.0238(6) 0.0230(6) -0.0034(5) -0.0014(5) 0.0001(5)
N1 0.0235(7) 0.0186(6) 0.0174(6) -0.0022(5) -0.0002(5) -0.0032(5)
N2 0.0248(7) 0.0215(7) 0.0217(7) -0.0010(5) -0.0025(5) -0.0039(6)
C1 0.0196(7) 0.0196(7) 0.0211(7) -0.0033(6) 0.0011(6) -0.0065(6)
C2 0.0175(7) 0.0220(7) 0.0194(7) -0.0054(6) 0.0000(6) -0.0051(6)
C3 0.0210(7) 0.0216(7) 0.0224(8) -0.0043(6) -0.0011(6) -0.0054(6)
C4 0.0230(8) 0.0291(9) 0.0211(8) -0.0028(6) -0.0014(6) -0.0087(7)
C5 0.0236(8) 0.0322(9) 0.0211(8) -0.0089(7) 0.0038(6) -0.0081(7)
C6 0.0238(8) 0.0230(8) 0.0277(8) -0.0099(7) 0.0013(7) -0.0042(6)
C7 0.0225(8) 0.0218(8) 0.0221(8) -0.0047(6) -0.0015(6) -0.0046(6)
C8 0.0220(8) 0.0261(8) 0.0311(9) -0.0018(7) 0.0024(7) 0.0021(7)
C9 0.0237(8) 0.0252(8) 0.0194(8) -0.0015(6) 0.0015(6) -0.0059(7)
C10 0.0204(7) 0.0216(7) 0.0218(8) -0.0040(6) 0.0010(6) -0.0040(6)
C11 0.0192(7) 0.0211(7) 0.0181(7) -0.0024(6) -0.0013(6) -0.0073(6)
C12 0.0209(7) 0.0242(8) 0.0192(7) -0.0045(6) 0.0009(6) -0.0061(6)
C13 0.0212(7) 0.0223(8) 0.0247(8) -0.0064(6) -0.0018(6) -0.0029(6)
C14 0.0228(8) 0.0228(8) 0.0176(7) -0.0028(6) 0.0015(6) -0.0070(6)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C1 1.6747(17) . ?
O1 C1 1.3345(19) . ?
O1 C8 1.443(2) . ?
N1 C1 1.336(2) . ?
N1 C2 1.422(2) . ?
N1 H1N 0.8800 . ?
N2 C13 1.339(2) . ?
N2 C9 1.347(2) . ?
C2 C3 1.393(2) . ?
C2 C7 1.399(2) . ?
C3 C4 1.389(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.388(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.390(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.388(2) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C10 1.381(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.401(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.393(2) . ?
C11 C14 1.467(2) . ?
C12 C13 1.389(2) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 C14 1.333(3) 2_766 ?
C14 H14 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
C1 O1 C8 119.07(13) . . ?
C1 N1 C2 129.31(14) . . ?
C1 N1 H1N 115.3 . . ?
C2 N1 H1N 115.3 . . ?
C13 N2 C9 116.43(14) . . ?
O1 C1 N1 113.15(14) . . ?
O1 C1 S1 124.85(12) . . ?
N1 C1 S1 121.96(12) . . ?
C3 C2 C7 119.68(15) . . ?
C3 C2 N1 124.14(14) . . ?
C7 C2 N1 116.10(14) . . ?
C4 C3 C2 119.60(15) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C5 C4 C3 120.77(16) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C4 C5 C6 119.69(16) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
C7 C6 C5 120.00(16) . . ?
C7 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C6 C7 C2 120.24(15) . . ?
C6 C7 H7 119.9 . . ?
C2 C7 H7 119.9 . . ?
O1 C8 H8A 109.5 . . ?
O1 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
O1 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N2 C9 C10 124.20(15) . . ?
N2 C9 H9 117.9 . . ?
C10 C9 H9 117.9 . . ?
C9 C10 C11 119.15(15) . . ?
C9 C10 H10 120.4 . . ?
C11 C10 H10 120.4 . . ?
C12 C11 C10 116.89(14) . . ?
C12 C11 C14 119.33(14) . . ?
C10 C11 C14 123.78(14) . . ?
C13 C12 C11 119.92(15) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
N2 C13 C12 123.40(15) . . ?
N2 C13 H13 118.3 . . ?
C12 C13 H13 118.3 . . ?
C14 C14 C11 125.71(19) 2_766 . ?
C14 C14 H14 117.1 2_766 . ?
C11 C14 H14 117.1 . . ?

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
C8 O1 C1 N1 -173.20(14) . . . . ?
C8 O1 C1 S1 9.0(2) . . . . ?
C2 N1 C1 O1 3.5(2) . . . . ?
C2 N1 C1 S1 -178.62(13) . . . . ?
C1 N1 C2 C3 31.3(3) . . . . ?
C1 N1 C2 C7 -152.08(16) . . . . ?
C7 C2 C3 C4 1.2(2) . . . . ?
N1 C2 C3 C4 177.73(15) . . . . ?
C2 C3 C4 C5 -1.5(2) . . . . ?
C3 C4 C5 C6 0.5(3) . . . . ?
C4 C5 C6 C7 0.7(3) . . . . ?
C5 C6 C7 C2 -1.0(3) . . . . ?
C3 C2 C7 C6 0.0(2) . . . . ?
N1 C2 C7 C6 -176.79(15) . . . . ?
C13 N2 C9 C10 0.5(3) . . . . ?
N2 C9 C10 C11 -0.4(3) . . . . ?
C9 C10 C11 C12 0.6(2) . . . . ?
C9 C10 C11 C14 -179.28(16) . . . . ?
C10 C11 C12 C13 -0.9(2) . . . . ?
C14 C11 C12 C13 178.95(15) . . . . ?
C9 N2 C13 C12 -0.9(2) . . . . ?
C11 C12 C13 N2 1.1(3) . . . . ?
C12 C11 C14 C14 -176.6(2) . . . 2_766 ?
C10 C11 C14 C14 3.3(3) . . . 2_766 ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        27.5
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.26
_refine_diff_density_min         -0.29
_refine_diff_density_rms         0.053

# Attachment '2.CIF'

data_shelxl2
_database_code_depnum_ccdc_archive 'CCDC 713702'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H10 N2, 2(C8 H8 N2 O3 S)'
_chemical_formula_sum            'C28 H26 N6 O6 S2'
_chemical_formula_weight         606.67

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

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

_cell_length_a                   7.378(8)
_cell_length_b                   7.956(10)
_cell_length_c                   12.339(15)
_cell_angle_alpha                101.02(5)
_cell_angle_beta                 95.14(3)
_cell_angle_gamma                99.78(3)
_cell_volume                     694.9(14)
_cell_formula_units_Z            1
_cell_measurement_temperature    98(2)
_cell_measurement_reflns_used    2379
_cell_measurement_theta_min      1.7
_cell_measurement_theta_max      30.4

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.450
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             316
_exptl_absorpt_coefficient_mu    0.247
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.644
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_process_details   'ABSCOR (Higashi, 1995)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      98(2)
_diffrn_radiation_wavelength     0.71070
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  AFC12\k/SATURN724
_diffrn_measurement_method       \w
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        '< 1'
_diffrn_reflns_number            6893
_diffrn_reflns_av_R_equivalents  0.034
_diffrn_reflns_av_sigmaI/netI    0.039
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.7
_diffrn_reflns_theta_max         26.5
_reflns_number_total             2863
_reflns_number_gt                2493
_reflns_threshold_expression     I>2\s(I)

_computing_data_collection       'CrystalClear (Rigaku, 2005)'
_computing_cell_refinement       CrystalClear
_computing_data_reduction        CrystalClear
_computing_structure_solution    'SIR-92 (Altomare et al., 1994)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  SHELXL97

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.098P)^2^+1.3266P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2863
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.081
_refine_ls_R_factor_gt           0.063
_refine_ls_wR_factor_ref         0.220
_refine_ls_wR_factor_gt          0.163
_refine_ls_goodness_of_fit_ref   1.22
_refine_ls_restrained_S_all      1.22
_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 0.72876(12) 0.95241(11) 0.38448(7) 0.0271(3) Uani 1 1 d . . .
O1 O 0.4276(3) 0.8667(3) 0.2344(2) 0.0260(6) Uani 1 1 d . . .
O2 O -0.0052(4) 0.0979(4) -0.1047(2) 0.0401(7) Uani 1 1 d . . .
O3 O 0.2272(4) -0.0354(3) -0.1051(2) 0.0354(7) Uani 1 1 d . . .
N1 N 0.5946(4) 0.6569(4) 0.2396(2) 0.0241(6) Uani 1 1 d . . .
H1N H 0.6978 0.6282 0.2653 0.029 Uiso 1 1 calc R . .
N2 N 0.1555(4) 0.0915(4) -0.0722(2) 0.0302(7) Uani 1 1 d . . .
N3 N 0.9305(4) 0.5549(4) 0.3181(2) 0.0256(6) Uani 1 1 d . . .
C1 C 0.5766(5) 0.8235(4) 0.2824(3) 0.0238(7) Uani 1 1 d . . .
C2 C 0.4755(5) 0.5237(4) 0.1614(3) 0.0239(7) Uani 1 1 d . . .
C3 C 0.2849(5) 0.5136(5) 0.1336(3) 0.0268(7) Uani 1 1 d . . .
H3 H 0.2268 0.6045 0.1673 0.032 Uiso 1 1 calc R . .
C4 C 0.1810(5) 0.3717(5) 0.0575(3) 0.0270(8) Uani 1 1 d . . .
H4 H 0.0518 0.3650 0.0389 0.032 Uiso 1 1 calc R . .
C5 C 0.2661(5) 0.2400(5) 0.0087(3) 0.0256(7) Uani 1 1 d . . .
C6 C 0.4537(5) 0.2457(5) 0.0347(3) 0.0264(7) Uani 1 1 d . . .
H6 H 0.5104 0.1543 0.0002 0.032 Uiso 1 1 calc R . .
C7 C 0.5575(5) 0.3865(5) 0.1117(3) 0.0272(7) Uani 1 1 d . . .
H7 H 0.6859 0.3902 0.1312 0.033 Uiso 1 1 calc R . .
C8 C 0.3922(5) 1.0377(5) 0.2767(3) 0.0313(8) Uani 1 1 d . . .
H8A H 0.3777 1.0505 0.3559 0.047 Uiso 1 1 calc R . .
H8B H 0.2783 1.0532 0.2356 0.047 Uiso 1 1 calc R . .
H8C H 0.4964 1.1259 0.2674 0.047 Uiso 1 1 calc R . .
C9 C 0.9453(5) 0.3941(4) 0.3300(3) 0.0260(7) Uani 1 1 d . . .
H9 H 0.8438 0.3016 0.2991 0.031 Uiso 1 1 calc R . .
C10 C 1.0992(5) 0.3546(5) 0.3843(3) 0.0263(7) Uani 1 1 d . . .
H10 H 1.1003 0.2382 0.3920 0.032 Uiso 1 1 calc R . .
C11 C 1.2541(5) 0.4868(4) 0.4283(3) 0.0239(7) Uani 1 1 d . . .
C12 C 1.2382(5) 0.6560(4) 0.4166(3) 0.0232(7) Uani 1 1 d . . .
H12 H 1.3376 0.7513 0.4461 0.028 Uiso 1 1 calc R . .
C13 C 1.0779(5) 0.6828(4) 0.3623(3) 0.0242(7) Uani 1 1 d . . .
H13 H 1.0705 0.7985 0.3555 0.029 Uiso 1 1 calc R . .
C14 C 1.4174(5) 0.4461(5) 0.4863(3) 0.0250(7) Uani 1 1 d . . .
H14 H 1.4056 0.3354 0.5061 0.030 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 0.0244(5) 0.0273(5) 0.0254(5) -0.0004(3) -0.0054(3) 0.0046(3)
O1 0.0223(12) 0.0255(12) 0.0283(13) 0.0027(10) -0.0040(10) 0.0060(9)
O2 0.0296(15) 0.0433(16) 0.0387(16) -0.0036(12) -0.0109(12) 0.0044(12)
O3 0.0360(15) 0.0312(14) 0.0330(14) -0.0055(11) -0.0011(12) 0.0065(12)
N1 0.0217(14) 0.0270(15) 0.0211(14) 0.0004(11) -0.0046(11) 0.0072(11)
N2 0.0284(16) 0.0346(17) 0.0226(15) 0.0015(13) -0.0033(12) 0.0007(13)
N3 0.0182(14) 0.0329(16) 0.0235(14) 0.0029(12) -0.0029(11) 0.0053(11)
C1 0.0223(16) 0.0292(17) 0.0210(16) 0.0039(13) 0.0018(12) 0.0098(13)
C2 0.0251(17) 0.0277(17) 0.0183(15) 0.0032(13) -0.0008(13) 0.0068(13)
C3 0.0241(17) 0.0309(18) 0.0246(17) 0.0010(14) 0.0010(13) 0.0096(14)
C4 0.0223(17) 0.0325(19) 0.0241(17) 0.0009(14) -0.0020(13) 0.0080(14)
C5 0.0246(17) 0.0309(18) 0.0188(15) 0.0037(13) -0.0011(13) 0.0023(14)
C6 0.0246(17) 0.0319(18) 0.0224(16) 0.0038(14) -0.0003(13) 0.0083(14)
C7 0.0207(16) 0.0375(19) 0.0228(16) 0.0046(14) -0.0024(13) 0.0087(14)
C8 0.0265(18) 0.0313(19) 0.0340(19) 0.0011(15) -0.0049(15) 0.0106(15)
C9 0.0236(17) 0.0247(17) 0.0278(17) 0.0019(13) -0.0013(13) 0.0058(13)
C10 0.0241(17) 0.0288(18) 0.0260(17) 0.0027(14) -0.0002(13) 0.0098(14)
C11 0.0232(17) 0.0297(17) 0.0182(15) 0.0012(13) 0.0010(13) 0.0091(13)
C12 0.0211(16) 0.0230(16) 0.0224(16) 0.0000(12) -0.0004(12) 0.0026(12)
C13 0.0246(17) 0.0262(17) 0.0225(16) 0.0031(13) 0.0009(13) 0.0100(13)
C14 0.0260(17) 0.0281(17) 0.0213(16) 0.0064(13) -0.0012(13) 0.0071(13)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C1 1.661(4) . ?
O1 C1 1.329(4) . ?
O1 C8 1.436(4) . ?
O2 N2 1.229(4) . ?
O3 N2 1.236(4) . ?
N1 C1 1.363(5) . ?
N1 C2 1.403(4) . ?
N1 H1N 0.8800 . ?
N2 C5 1.461(5) . ?
N3 C9 1.336(5) . ?
N3 C13 1.350(5) . ?
C2 C3 1.402(5) . ?
C2 C7 1.403(5) . ?
C3 C4 1.385(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.379(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.383(5) . ?
C6 C7 1.384(5) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C10 1.380(5) . ?
C9 H9 0.9500 . ?
C10 C11 1.403(5) . ?
C10 H10 0.9500 . ?
C11 C12 1.404(5) . ?
C11 C14 1.462(5) . ?
C12 C13 1.376(5) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 C14 1.340(7) 2_866 ?
C14 H14 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
C1 O1 C8 117.2(3) . . ?
C1 N1 C2 130.5(3) . . ?
C1 N1 H1N 114.8 . . ?
C2 N1 H1N 114.8 . . ?
O2 N2 O3 122.7(3) . . ?
O2 N2 C5 118.6(3) . . ?
O3 N2 C5 118.7(3) . . ?
C9 N3 C13 116.4(3) . . ?
O1 C1 N1 112.9(3) . . ?
O1 C1 S1 125.6(3) . . ?
N1 C1 S1 121.5(3) . . ?
C3 C2 C7 118.7(3) . . ?
C3 C2 N1 125.9(3) . . ?
C7 C2 N1 115.3(3) . . ?
C4 C3 C2 120.3(3) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C5 C4 C3 119.6(3) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
C4 C5 C6 121.4(3) . . ?
C4 C5 N2 119.2(3) . . ?
C6 C5 N2 119.3(3) . . ?
C5 C6 C7 119.1(3) . . ?
C5 C6 H6 120.5 . . ?
C7 C6 H6 120.5 . . ?
C6 C7 C2 120.8(3) . . ?
C6 C7 H7 119.6 . . ?
C2 C7 H7 119.6 . . ?
O1 C8 H8A 109.5 . . ?
O1 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
O1 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N3 C9 C10 123.9(3) . . ?
N3 C9 H9 118.1 . . ?
C10 C9 H9 118.1 . . ?
C9 C10 C11 119.8(3) . . ?
C9 C10 H10 120.1 . . ?
C11 C10 H10 120.1 . . ?
C10 C11 C12 116.3(3) . . ?
C10 C11 C14 120.1(3) . . ?
C12 C11 C14 123.5(3) . . ?
C13 C12 C11 119.6(3) . . ?
C13 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
N3 C13 C12 124.0(3) . . ?
N3 C13 H13 118.0 . . ?
C12 C13 H13 118.0 . . ?
C14 C14 C11 124.6(4) 2_866 . ?
C14 C14 H14 117.7 2_866 . ?
C11 C14 H14 117.7 . . ?

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
C8 O1 C1 N1 177.6(3) . . . . ?
C8 O1 C1 S1 -1.9(5) . . . . ?
C2 N1 C1 O1 -5.7(5) . . . . ?
C2 N1 C1 S1 173.9(3) . . . . ?
C1 N1 C2 C3 -21.0(6) . . . . ?
C1 N1 C2 C7 162.1(3) . . . . ?
C7 C2 C3 C4 -0.9(5) . . . . ?
N1 C2 C3 C4 -177.7(3) . . . . ?
C2 C3 C4 C5 -0.1(5) . . . . ?
C3 C4 C5 C6 0.4(5) . . . . ?
C3 C4 C5 N2 -179.5(3) . . . . ?
O2 N2 C5 C4 8.7(5) . . . . ?
O3 N2 C5 C4 -171.2(3) . . . . ?
O2 N2 C5 C6 -171.3(3) . . . . ?
O3 N2 C5 C6 8.9(5) . . . . ?
C4 C5 C6 C7 0.3(5) . . . . ?
N2 C5 C6 C7 -179.8(3) . . . . ?
C5 C6 C7 C2 -1.3(5) . . . . ?
C3 C2 C7 C6 1.6(5) . . . . ?
N1 C2 C7 C6 178.8(3) . . . . ?
C13 N3 C9 C10 0.4(5) . . . . ?
N3 C9 C10 C11 -1.8(5) . . . . ?
C9 C10 C11 C12 2.1(5) . . . . ?
C9 C10 C11 C14 179.8(3) . . . . ?
C10 C11 C12 C13 -1.3(5) . . . . ?
C14 C11 C12 C13 -178.8(3) . . . . ?
C9 N3 C13 C12 0.5(5) . . . . ?
C11 C12 C13 N3 0.0(5) . . . . ?
C10 C11 C14 C14 167.6(4) . . . 2_866 ?
C12 C11 C14 C14 -15.0(6) . . . 2_866 ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        26.5
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.69
_refine_diff_density_min         -0.76
_refine_diff_density_rms         0.118

# Attachment '3.CIF'

data_shelxl3
_database_code_depnum_ccdc_archive 'CCDC 713703'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H10 N2, 2(C9 H11 N O S)'
_chemical_formula_sum            'C30 H32 N4 O2 S2'
_chemical_formula_weight         544.72

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

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

_cell_length_a                   8.0156(17)
_cell_length_b                   9.3410(17)
_cell_length_c                   9.916(3)
_cell_angle_alpha                98.324(7)
_cell_angle_beta                 110.766(5)
_cell_angle_gamma                91.310(2)
_cell_volume                     684.7(3)
_cell_formula_units_Z            1
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    1417
_cell_measurement_theta_min      2.7
_cell_measurement_theta_max      30.1

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             288
_exptl_absorpt_coefficient_mu    0.230
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.913
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_process_details   'ABSCOR (Higashi, 1995)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71070
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  AFC12\k/SATURN724
_diffrn_measurement_method       \w
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        '< 1'
_diffrn_reflns_number            7075
_diffrn_reflns_av_R_equivalents  0.024
_diffrn_reflns_av_sigmaI/netI    0.026
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.2
_diffrn_reflns_theta_max         26.5
_reflns_number_total             2810
_reflns_number_gt                2625
_reflns_threshold_expression     I>2\s(I)

_computing_data_collection       'CrystalClear (Rigaku, 2005)'
_computing_cell_refinement       CrystalClear
_computing_data_reduction        CrystalClear
_computing_structure_solution    'SIR-92 (Altomare et al., 1994)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  SHELXL97

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0594P)^2^+0.2824P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2810
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.046
_refine_ls_R_factor_gt           0.043
_refine_ls_wR_factor_ref         0.115
_refine_ls_wR_factor_gt          0.111
_refine_ls_goodness_of_fit_ref   1.05
_refine_ls_restrained_S_all      1.05
_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 0.33095(6) 0.66931(4) 0.68643(4) 0.03339(15) Uani 1 1 d . . .
O1 O 0.34482(15) 0.40446(12) 0.55227(12) 0.0296(3) Uani 1 1 d . . .
N1 N 0.54365(17) 0.46298(14) 0.77869(13) 0.0274(3) Uani 1 1 d . . .
H1N H 0.5968 0.5309 0.8548 0.033 Uiso 1 1 calc R . .
N2 N 0.74042(18) 0.68024(14) 1.05189(14) 0.0315(3) Uani 1 1 d . . .
C1 C 0.4083(2) 0.50596(16) 0.67085(16) 0.0261(3) Uani 1 1 d . . .
C2 C 0.6148(2) 0.32521(16) 0.78959(16) 0.0258(3) Uani 1 1 d . . .
C3 C 0.5997(2) 0.21771(17) 0.67179(17) 0.0298(3) Uani 1 1 d . . .
H3 H 0.5393 0.2340 0.5745 0.036 Uiso 1 1 calc R . .
C4 C 0.6735(2) 0.08643(18) 0.69756(18) 0.0337(4) Uani 1 1 d . . .
H4 H 0.6614 0.0126 0.6172 0.040 Uiso 1 1 calc R . .
C5 C 0.7644(2) 0.06181(18) 0.83871(19) 0.0353(4) Uani 1 1 d . . .
H5 H 0.8144 -0.0281 0.8553 0.042 Uiso 1 1 calc R . .
C6 C 0.7812(2) 0.16961(18) 0.95503(18) 0.0349(4) Uani 1 1 d . . .
H6 H 0.8443 0.1538 1.0520 0.042 Uiso 1 1 calc R . .
C7 C 0.7070(2) 0.30076(17) 0.93157(17) 0.0303(3) Uani 1 1 d . . .
H7 H 0.7191 0.3740 1.0124 0.036 Uiso 1 1 calc R . .
C8 C 0.2021(2) 0.43604(17) 0.42439(17) 0.0300(3) Uani 1 1 d . . .
H8A H 0.2382 0.5227 0.3913 0.036 Uiso 1 1 calc R . .
H8B H 0.0927 0.4545 0.4466 0.036 Uiso 1 1 calc R . .
C9 C 0.1686(2) 0.30400(18) 0.30851(18) 0.0347(4) Uani 1 1 d . . .
H9A H 0.0727 0.3198 0.2190 0.052 Uiso 1 1 calc R . .
H9B H 0.1332 0.2193 0.3430 0.052 Uiso 1 1 calc R . .
H9C H 0.2782 0.2870 0.2882 0.052 Uiso 1 1 calc R . .
C10 C 0.8717(2) 0.65593(18) 1.17380(18) 0.0336(4) Uani 1 1 d . . .
H10 H 0.9224 0.5651 1.1714 0.040 Uiso 1 1 calc R . .
C11 C 0.9376(2) 0.75424(17) 1.30206(17) 0.0300(3) Uani 1 1 d . . .
H11 H 1.0307 0.7306 1.3846 0.036 Uiso 1 1 calc R . .
C12 C 0.8661(2) 0.88904(16) 1.30950(16) 0.0257(3) Uani 1 1 d . . .
C13 C 0.7303(2) 0.91505(17) 1.18376(17) 0.0299(3) Uani 1 1 d . . .
H13 H 0.6766 1.0047 1.1832 0.036 Uiso 1 1 calc R . .
C14 C 0.6734(2) 0.81026(17) 1.05940(17) 0.0317(4) Uani 1 1 d . . .
H14 H 0.5819 0.8316 0.9746 0.038 Uiso 1 1 calc R . .
C15 C 0.9283(2) 1.00159(16) 1.43969(16) 0.0275(3) Uani 1 1 d . . .
H15 H 0.8609 1.0841 1.4383 0.033 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 0.0393(3) 0.0283(2) 0.0269(2) -0.00046(16) 0.00647(18) 0.01182(17)
O1 0.0318(6) 0.0266(5) 0.0233(5) -0.0007(4) 0.0029(4) 0.0070(4)
N1 0.0324(7) 0.0241(6) 0.0213(6) 0.0000(5) 0.0057(5) 0.0049(5)
N2 0.0339(7) 0.0289(7) 0.0264(7) -0.0016(5) 0.0068(6) 0.0018(5)
C1 0.0285(7) 0.0266(7) 0.0231(7) 0.0015(6) 0.0100(6) 0.0032(6)
C2 0.0261(7) 0.0236(7) 0.0267(7) 0.0037(6) 0.0084(6) 0.0036(6)
C3 0.0316(8) 0.0297(8) 0.0259(7) 0.0033(6) 0.0082(6) 0.0075(6)
C4 0.0380(9) 0.0283(8) 0.0312(8) -0.0009(6) 0.0099(7) 0.0066(7)
C5 0.0366(9) 0.0265(8) 0.0375(9) 0.0056(7) 0.0067(7) 0.0080(6)
C6 0.0373(9) 0.0297(8) 0.0292(8) 0.0065(6) 0.0011(7) 0.0024(7)
C7 0.0351(8) 0.0256(8) 0.0246(7) 0.0013(6) 0.0051(6) 0.0014(6)
C8 0.0276(8) 0.0308(8) 0.0262(8) 0.0019(6) 0.0039(6) 0.0077(6)
C9 0.0348(9) 0.0315(8) 0.0279(8) -0.0022(6) 0.0022(7) 0.0023(7)
C10 0.0351(9) 0.0270(8) 0.0317(8) -0.0008(6) 0.0055(7) 0.0052(6)
C11 0.0323(8) 0.0251(8) 0.0271(8) 0.0024(6) 0.0046(6) 0.0035(6)
C12 0.0276(7) 0.0239(7) 0.0243(7) 0.0024(6) 0.0085(6) 0.0016(6)
C13 0.0322(8) 0.0257(7) 0.0286(8) 0.0029(6) 0.0076(7) 0.0049(6)
C14 0.0325(8) 0.0315(8) 0.0253(8) 0.0033(6) 0.0039(6) 0.0040(6)
C15 0.0309(8) 0.0223(7) 0.0267(7) 0.0007(6) 0.0084(6) 0.0042(6)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C1 1.6672(16) . ?
O1 C1 1.3309(18) . ?
O1 C8 1.4490(18) . ?
N1 C1 1.343(2) . ?
N1 C2 1.4225(19) . ?
N1 H1N 0.8800 . ?
N2 C14 1.342(2) . ?
N2 C10 1.345(2) . ?
C2 C7 1.394(2) . ?
C2 C3 1.393(2) . ?
C3 C4 1.391(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.386(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.382(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.388(2) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C9 1.507(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.380(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.399(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.391(2) . ?
C12 C15 1.465(2) . ?
C13 C14 1.385(2) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 C15 1.338(3) 2_778 ?
C15 H15 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
C1 O1 C8 119.26(12) . . ?
C1 N1 C2 130.32(13) . . ?
C1 N1 H1N 114.8 . . ?
C2 N1 H1N 114.8 . . ?
C14 N2 C10 115.99(13) . . ?
O1 C1 N1 112.58(13) . . ?
O1 C1 S1 124.54(11) . . ?
N1 C1 S1 122.88(11) . . ?
C7 C2 C3 119.48(14) . . ?
C7 C2 N1 115.23(13) . . ?
C3 C2 N1 125.29(13) . . ?
C2 C3 C4 119.57(14) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C5 C4 C3 120.95(15) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
C4 C5 C6 119.21(15) . . ?
C4 C5 H5 120.4 . . ?
C6 C5 H5 120.4 . . ?
C7 C6 C5 120.67(15) . . ?
C7 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C2 C7 C6 120.10(15) . . ?
C2 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
O1 C8 C9 106.10(12) . . ?
O1 C8 H8A 110.5 . . ?
C9 C8 H8A 110.5 . . ?
O1 C8 H8B 110.5 . . ?
C9 C8 H8B 110.5 . . ?
H8A C8 H8B 108.7 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N2 C10 C11 124.29(15) . . ?
N2 C10 H10 117.9 . . ?
C11 C10 H10 117.9 . . ?
C12 C11 C10 119.41(15) . . ?
C12 C11 H11 120.3 . . ?
C10 C11 H11 120.3 . . ?
C11 C12 C13 116.63(14) . . ?
C11 C12 C15 123.64(14) . . ?
C13 C12 C15 119.72(14) . . ?
C14 C13 C12 119.99(14) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
N2 C14 C13 123.68(14) . . ?
N2 C14 H14 118.2 . . ?
C13 C14 H14 118.2 . . ?
C15 C15 C12 125.73(18) 2_778 . ?
C15 C15 H15 117.1 2_778 . ?
C12 C15 H15 117.1 . . ?

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
C8 O1 C1 N1 -178.01(13) . . . . ?
C8 O1 C1 S1 1.9(2) . . . . ?
C2 N1 C1 O1 -6.7(2) . . . . ?
C2 N1 C1 S1 173.39(12) . . . . ?
C1 N1 C2 C7 -157.24(16) . . . . ?
C1 N1 C2 C3 23.2(3) . . . . ?
C7 C2 C3 C4 1.3(2) . . . . ?
N1 C2 C3 C4 -179.08(14) . . . . ?
C2 C3 C4 C5 -1.0(3) . . . . ?
C3 C4 C5 C6 0.1(3) . . . . ?
C4 C5 C6 C7 0.6(3) . . . . ?
C3 C2 C7 C6 -0.7(2) . . . . ?
N1 C2 C7 C6 179.65(15) . . . . ?
C5 C6 C7 C2 -0.2(3) . . . . ?
C1 O1 C8 C9 176.95(13) . . . . ?
C14 N2 C10 C11 0.5(3) . . . . ?
N2 C10 C11 C12 0.0(3) . . . . ?
C10 C11 C12 C13 -0.1(2) . . . . ?
C10 C11 C12 C15 -179.11(15) . . . . ?
C11 C12 C13 C14 -0.4(2) . . . . ?
C15 C12 C13 C14 178.66(15) . . . . ?
C10 N2 C14 C13 -1.1(2) . . . . ?
C12 C13 C14 N2 1.0(3) . . . . ?
C11 C12 C15 C15 8.1(3) . . . 2_778 ?
C13 C12 C15 C15 -170.9(2) . . . 2_778 ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        26.5
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.29
_refine_diff_density_min         -0.27
_refine_diff_density_rms         0.048

# Attachment '4.cif'

data_shelxl4
_database_code_depnum_ccdc_archive 'CCDC 713704'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H20 N4 O6 S2, C10 H8 N2'
_chemical_formula_sum            'C28 H28 N6 O6 S2 '
_chemical_formula_weight         608.70

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/n'
_symmetry_space_group_name_Hall  '-P 2yn'

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                   9.727(7)
_cell_length_b                   14.640(9)
_cell_length_c                   10.112(7)
_cell_angle_alpha                90
_cell_angle_beta                 100.83(2)
_cell_angle_gamma                90
_cell_volume                     1414.3(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    3974
_cell_measurement_theta_min      2.5
_cell_measurement_theta_max      30.3

_exptl_crystal_description       prism
_exptl_crystal_colour            pale-yellow
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.429
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             636
_exptl_absorpt_coefficient_mu    0.243
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.824
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_process_details   'ABSCOR (Higashi, 1995)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      153(2)
_diffrn_radiation_wavelength     0.71070
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  AFC12\k/SATURN724
_diffrn_measurement_method       \w
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        '< 1'
_diffrn_reflns_number            12891
_diffrn_reflns_av_R_equivalents  0.086
_diffrn_reflns_av_sigmaI/netI    0.054
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.5
_diffrn_reflns_theta_max         25.0
_reflns_number_total             2481
_reflns_number_gt                2062
_reflns_threshold_expression     I>2\s(I)

_computing_data_collection       'CrystalClear (Rigaku, 2005)'
_computing_cell_refinement       CrystalClear
_computing_data_reduction        CrystalClear
_computing_structure_solution    'SIR-92 (Altomare et al., 1994)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  SHELXL97

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.082P)^2^+2.0145P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2481
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.113
_refine_ls_R_factor_gt           0.094
_refine_ls_wR_factor_ref         0.225
_refine_ls_wR_factor_gt          0.214
_refine_ls_goodness_of_fit_ref   1.21
_refine_ls_restrained_S_all      1.21
_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 0.66278(12) 0.33698(8) 0.20924(15) 0.0572(5) Uani 1 1 d . . .
O1 O 0.7287(3) 0.16058(19) 0.2215(3) 0.0479(9) Uani 1 1 d . . .
O2 O 0.3268(4) -0.2277(2) 0.1235(4) 0.0644(10) Uani 1 1 d . . .
O3 O 0.1262(4) -0.1606(2) 0.0599(4) 0.0635(10) Uani 1 1 d . . .
N1 N 0.4997(4) 0.1909(3) 0.1588(4) 0.0460(10) Uani 1 1 d . . .
H1N H 0.4339 0.2326 0.1399 0.055 Uiso 1 1 calc R . .
N2 N 0.2539(4) -0.1595(3) 0.0969(4) 0.0508(10) Uani 1 1 d . . .
N3 N 0.2594(4) 0.3251(2) 0.0760(4) 0.0472(10) Uani 1 1 d . . .
C1 C 0.6321(5) 0.2256(3) 0.1963(5) 0.0455(11) Uani 1 1 d . . .
C2 C 0.4505(4) 0.1005(3) 0.1454(5) 0.0415(10) Uani 1 1 d . . .
C3 C 0.5312(5) 0.0216(3) 0.1766(5) 0.0416(11) Uani 1 1 d . . .
H3 H 0.6292 0.0261 0.2092 0.050 Uiso 1 1 calc R . .
C4 C 0.4661(4) -0.0640(3) 0.1591(4) 0.0415(11) Uani 1 1 d . . .
H4 H 0.5202 -0.1180 0.1789 0.050 Uiso 1 1 calc R . .
C5 C 0.3233(5) -0.0700(3) 0.1131(5) 0.0428(11) Uani 1 1 d . . .
C6 C 0.2422(5) 0.0074(3) 0.0800(5) 0.0554(13) Uani 1 1 d . . .
H6 H 0.1446 0.0026 0.0456 0.067 Uiso 1 1 calc R . .
C7 C 0.3069(5) 0.0917(3) 0.0983(6) 0.0562(14) Uani 1 1 d . . .
H7 H 0.2518 0.1453 0.0783 0.067 Uiso 1 1 calc R . .
C8 C 0.8753(4) 0.1873(3) 0.2678(5) 0.0479(12) Uani 1 1 d . . .
H8A H 0.8867 0.2195 0.3553 0.057 Uiso 1 1 calc R . .
H8B H 0.9068 0.2282 0.2014 0.057 Uiso 1 1 calc R . .
C9 C 0.9590(5) 0.0993(3) 0.2824(6) 0.0607(14) Uani 1 1 d . . .
H9A H 1.0583 0.1132 0.3136 0.091 Uiso 1 1 calc R . .
H9B H 0.9466 0.0682 0.1951 0.091 Uiso 1 1 calc R . .
H9C H 0.9261 0.0595 0.3479 0.091 Uiso 1 1 calc R . .
C10 C 0.1218(5) 0.3063(3) 0.0351(5) 0.0508(12) Uani 1 1 d . . .
H10 H 0.0947 0.2440 0.0263 0.061 Uiso 1 1 calc R . .
C11 C 0.0182(4) 0.3715(3) 0.0054(5) 0.0483(12) Uani 1 1 d . . .
H11 H -0.0769 0.3536 -0.0213 0.058 Uiso 1 1 calc R . .
C12 C 0.0538(4) 0.4636(3) 0.0148(4) 0.0372(10) Uani 1 1 d . . .
C13 C 0.1957(5) 0.4831(3) 0.0532(5) 0.0476(12) Uani 1 1 d . . .
H13 H 0.2261 0.5448 0.0585 0.057 Uiso 1 1 calc R . .
C14 C 0.2933(5) 0.4136(3) 0.0839(5) 0.0509(12) Uani 1 1 d . . .
H14 H 0.3889 0.4298 0.1119 0.061 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 0.0370(7) 0.0371(7) 0.0933(11) -0.0003(6) 0.0018(6) -0.0012(5)
O1 0.0293(16) 0.0365(17) 0.076(2) -0.0027(15) 0.0039(15) 0.0026(13)
O2 0.052(2) 0.0386(19) 0.100(3) -0.0010(18) 0.008(2) 0.0004(16)
O3 0.041(2) 0.054(2) 0.093(3) -0.0013(19) 0.0077(19) -0.0112(16)
N1 0.0315(19) 0.0356(19) 0.069(3) 0.0000(18) 0.0043(18) -0.0003(15)
N2 0.041(2) 0.049(2) 0.062(3) -0.005(2) 0.0096(19) -0.0077(19)
N3 0.033(2) 0.036(2) 0.070(3) -0.0005(18) 0.0041(18) 0.0058(16)
C1 0.041(3) 0.037(2) 0.058(3) -0.001(2) 0.008(2) 0.001(2)
C2 0.039(2) 0.032(2) 0.053(3) -0.003(2) 0.008(2) -0.0007(19)
C3 0.030(2) 0.040(2) 0.054(3) -0.002(2) 0.0050(19) -0.0014(18)
C4 0.034(2) 0.033(2) 0.056(3) -0.004(2) 0.005(2) -0.0018(18)
C5 0.042(2) 0.036(2) 0.049(3) -0.005(2) 0.007(2) -0.0077(19)
C6 0.031(2) 0.049(3) 0.081(4) -0.007(3) -0.002(2) -0.002(2)
C7 0.035(2) 0.036(3) 0.094(4) -0.004(3) 0.002(2) 0.005(2)
C8 0.028(2) 0.044(3) 0.069(3) 0.004(2) 0.003(2) -0.0001(19)
C9 0.035(3) 0.052(3) 0.091(4) 0.003(3) 0.001(3) 0.006(2)
C10 0.036(2) 0.038(2) 0.075(3) 0.001(2) 0.002(2) -0.003(2)
C11 0.026(2) 0.044(3) 0.072(3) 0.000(2) 0.005(2) -0.0011(19)
C12 0.027(2) 0.040(2) 0.044(2) -0.0009(19) 0.0040(18) 0.0009(17)
C13 0.037(2) 0.033(2) 0.070(3) -0.001(2) 0.001(2) -0.0054(19)
C14 0.029(2) 0.043(3) 0.077(3) 0.001(2) 0.000(2) -0.0011(19)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C1 1.659(5) . ?
O1 C1 1.328(5) . ?
O1 C8 1.468(5) . ?
O2 N2 1.225(5) . ?
O3 N2 1.229(5) . ?
N1 C1 1.369(6) . ?
N1 C2 1.405(6) . ?
N1 H1N 0.8800 . ?
N2 C5 1.469(6) . ?
N3 C14 1.336(6) . ?
N3 C10 1.352(6) . ?
C2 C7 1.395(6) . ?
C2 C3 1.399(6) . ?
C3 C4 1.400(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.383(6) . ?
C4 H4 0.9500 . ?
C5 C6 1.385(7) . ?
C6 C7 1.382(7) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C9 1.516(6) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.380(6) . ?
C10 H10 0.9500 . ?
C11 C12 1.390(6) . ?
C11 H11 0.9500 . ?
C12 C13 1.392(6) . ?
C12 C12 1.485(8) 3_565 ?
C13 C14 1.385(6) . ?
C13 H13 0.9500 . ?
C14 H14 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
C1 O1 C8 118.7(3) . . ?
C1 N1 C2 131.4(4) . . ?
C1 N1 H1N 114.3 . . ?
C2 N1 H1N 114.3 . . ?
O2 N2 O3 124.5(4) . . ?
O2 N2 C5 118.0(4) . . ?
O3 N2 C5 117.6(4) . . ?
C14 N3 C10 115.7(4) . . ?
O1 C1 N1 112.5(4) . . ?
O1 C1 S1 125.3(3) . . ?
N1 C1 S1 122.1(3) . . ?
C7 C2 C3 118.9(4) . . ?
C7 C2 N1 114.9(4) . . ?
C3 C2 N1 126.1(4) . . ?
C2 C3 C4 119.3(4) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 H3 120.4 . . ?
C5 C4 C3 120.1(4) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C5 C6 121.3(4) . . ?
C4 C5 N2 120.4(4) . . ?
C6 C5 N2 118.3(4) . . ?
C7 C6 C5 118.3(4) . . ?
C7 C6 H6 120.9 . . ?
C5 C6 H6 120.9 . . ?
C6 C7 C2 122.0(4) . . ?
C6 C7 H7 119.0 . . ?
C2 C7 H7 119.0 . . ?
O1 C8 C9 106.0(4) . . ?
O1 C8 H8A 110.5 . . ?
C9 C8 H8A 110.5 . . ?
O1 C8 H8B 110.5 . . ?
C9 C8 H8B 110.5 . . ?
H8A C8 H8B 108.7 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N3 C10 C11 124.5(4) . . ?
N3 C10 H10 117.7 . . ?
C11 C10 H10 117.7 . . ?
C10 C11 C12 119.5(4) . . ?
C10 C11 H11 120.2 . . ?
C12 C11 H11 120.2 . . ?
C11 C12 C13 116.1(4) . . ?
C11 C12 C12 121.7(5) . 3_565 ?
C13 C12 C12 122.2(5) . 3_565 ?
C14 C13 C12 120.9(4) . . ?
C14 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
N3 C14 C13 123.2(4) . . ?
N3 C14 H14 118.4 . . ?
C13 C14 H14 118.4 . . ?

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
C8 O1 C1 N1 -177.7(4) . . . . ?
C8 O1 C1 S1 1.5(6) . . . . ?
C2 N1 C1 O1 1.2(7) . . . . ?
C2 N1 C1 S1 -178.0(4) . . . . ?
C1 N1 C2 C7 -177.1(5) . . . . ?
C1 N1 C2 C3 4.0(8) . . . . ?
C7 C2 C3 C4 0.4(7) . . . . ?
N1 C2 C3 C4 179.2(4) . . . . ?
C2 C3 C4 C5 -0.8(7) . . . . ?
C3 C4 C5 C6 1.7(7) . . . . ?
C3 C4 C5 N2 -178.9(4) . . . . ?
O2 N2 C5 C4 -1.0(7) . . . . ?
O3 N2 C5 C4 177.7(4) . . . . ?
O2 N2 C5 C6 178.4(4) . . . . ?
O3 N2 C5 C6 -2.9(7) . . . . ?
C4 C5 C6 C7 -2.1(8) . . . . ?
N2 C5 C6 C7 178.4(5) . . . . ?
C5 C6 C7 C2 1.7(8) . . . . ?
C3 C2 C7 C6 -0.8(8) . . . . ?
N1 C2 C7 C6 -179.8(5) . . . . ?
C1 O1 C8 C9 -177.9(4) . . . . ?
C14 N3 C10 C11 -1.6(8) . . . . ?
N3 C10 C11 C12 1.1(8) . . . . ?
C10 C11 C12 C13 0.7(7) . . . . ?
C10 C11 C12 C12 -179.4(5) . . . 3_565 ?
C11 C12 C13 C14 -2.0(7) . . . . ?
C12 C12 C13 C14 178.2(5) 3_565 . . . ?
C10 N3 C14 C13 0.2(7) . . . . ?
C12 C13 C14 N3 1.6(8) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.0
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.36
_refine_diff_density_min         -0.33
_refine_diff_density_rms         0.068

# Attachment '5.CIF'

data_5
_database_code_depnum_ccdc_archive 'CCDC 713705'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H13 N O S, 0.5(C12 H10 N2)'
_chemical_formula_sum            'C16 H18 N2 O S'
_chemical_formula_weight         286.39

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2/c'
_symmetry_space_group_name_Hall  '-C 2yc'

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                   11.454(4)
_cell_length_b                   14.950(6)
_cell_length_c                   17.707(7)
_cell_angle_alpha                90
_cell_angle_beta                 95.738(11)
_cell_angle_gamma                90
_cell_volume                     3017(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    98(2)
_cell_measurement_reflns_used    9397
_cell_measurement_theta_min      1.8
_cell_measurement_theta_max      30.5

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1216
_exptl_absorpt_coefficient_mu    0.212
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      98(2)
_diffrn_radiation_wavelength     0.71070
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  AFC12\k/SATURN724
_diffrn_measurement_method       \w
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        '< 1'
_diffrn_reflns_number            13387
_diffrn_reflns_av_R_equivalents  0.043
_diffrn_reflns_av_sigmaI/netI    0.032
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.3
_diffrn_reflns_theta_max         25.0
_reflns_number_total             2658
_reflns_number_gt                2496
_reflns_threshold_expression     I>2\s(I)

_computing_data_collection       'CrystalClear (Rigaku, 2005)'
_computing_cell_refinement       CrystalClear
_computing_data_reduction        CrystalClear
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  SHELXL97

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.1181P)^2^+3.524P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2658
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.078
_refine_ls_R_factor_gt           0.072
_refine_ls_wR_factor_ref         0.214
_refine_ls_wR_factor_gt          0.201
_refine_ls_goodness_of_fit_ref   1.20
_refine_ls_restrained_S_all      1.20
_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 0.45389(6) 0.75096(4) 0.47674(4) 0.0367(3) Uani 1 1 d . . .
O1 O 0.28641(17) 0.63188(13) 0.43279(11) 0.0391(5) Uani 1 1 d . . .
N1 N 0.3807(2) 0.60880(14) 0.54661(13) 0.0332(6) Uani 1 1 d . . .
H1N H 0.4352 0.6245 0.5828 0.040 Uiso 1 1 calc R . .
N2 N 0.6023(2) 0.61951(16) 0.65296(14) 0.0407(6) Uani 1 1 d . . .
C1 C 0.3692(2) 0.66122(18) 0.48496(16) 0.0342(6) Uani 1 1 d . . .
C2 C 0.3148(2) 0.53061(17) 0.56047(15) 0.0331(6) Uani 1 1 d . . .
C3 C 0.1930(3) 0.52920(19) 0.54888(18) 0.0408(7) Uani 1 1 d . . .
H3 H 0.1510 0.5801 0.5289 0.049 Uiso 1 1 calc R . .
C4 C 0.1336(3) 0.45288(19) 0.56681(17) 0.0404(7) Uani 1 1 d . . .
H4 H 0.0504 0.4518 0.5589 0.048 Uiso 1 1 calc R . .
C5 C 0.1930(3) 0.37796(19) 0.59603(16) 0.0379(7) Uani 1 1 d . . .
H5 H 0.1512 0.3258 0.6079 0.046 Uiso 1 1 calc R . .
C6 C 0.3140(3) 0.38018(19) 0.60771(16) 0.0364(7) Uani 1 1 d . . .
H6 H 0.3558 0.3291 0.6276 0.044 Uiso 1 1 calc R . .
C7 C 0.3749(2) 0.45663(18) 0.59062(15) 0.0337(6) Uani 1 1 d . . .
H7 H 0.4581 0.4581 0.5997 0.040 Uiso 1 1 calc R . .
C8 C 0.2587(3) 0.6825(2) 0.36215(16) 0.0435(7) Uani 1 1 d . . .
H8 H 0.2641 0.7480 0.3732 0.052 Uiso 1 1 calc R . .
C9 C 0.3449(3) 0.6579(3) 0.30596(19) 0.0564(9) Uani 1 1 d . . .
H9A H 0.4240 0.6765 0.3260 0.085 Uiso 1 1 calc R . .
H9B H 0.3228 0.6883 0.2576 0.085 Uiso 1 1 calc R . .
H9C H 0.3436 0.5930 0.2980 0.085 Uiso 1 1 calc R . .
C10 C 0.1338(3) 0.6583(3) 0.3352(2) 0.0574(9) Uani 1 1 d . . .
H10A H 0.0821 0.6772 0.3731 0.086 Uiso 1 1 calc R . .
H10B H 0.1275 0.5934 0.3280 0.086 Uiso 1 1 calc R . .
H10C H 0.1104 0.6885 0.2870 0.086 Uiso 1 1 calc R . .
C11 C 0.6469(3) 0.6061(3) 0.72474(19) 0.0652(12) Uani 1 1 d . . .
H11 H 0.5937 0.5985 0.7621 0.078 Uiso 1 1 calc R . .
C12 C 0.7649(3) 0.6026(3) 0.74796(18) 0.0585(10) Uani 1 1 d . . .
H12 H 0.7910 0.5925 0.7999 0.070 Uiso 1 1 calc R . .
C13 C 0.8460(2) 0.61363(16) 0.69551(15) 0.0313(6) Uani 1 1 d . . .
C14 C 0.8005(2) 0.6268(2) 0.62057(16) 0.0361(7) Uani 1 1 d . . .
H14 H 0.8518 0.6341 0.5820 0.043 Uiso 1 1 calc R . .
C15 C 0.6802(2) 0.62927(19) 0.60237(16) 0.0359(7) Uani 1 1 d . . .
H15 H 0.6514 0.6385 0.5508 0.043 Uiso 1 1 calc R . .
C16 C 0.9734(2) 0.61271(17) 0.71509(16) 0.0333(6) Uani 1 1 d . . .
H16 H 1.0215 0.6121 0.6744 0.040 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 0.0414(5) 0.0261(5) 0.0418(5) -0.0004(3) 0.0001(4) 0.0011(3)
O1 0.0406(11) 0.0389(11) 0.0365(11) -0.0053(8) -0.0018(8) 0.0006(9)
N1 0.0331(12) 0.0285(12) 0.0372(13) -0.0023(9) -0.0006(10) -0.0028(9)
N2 0.0380(14) 0.0443(15) 0.0394(14) -0.0052(11) 0.0018(11) -0.0030(11)
C1 0.0327(14) 0.0307(14) 0.0386(15) -0.0084(11) 0.0005(11) 0.0040(11)
C2 0.0351(14) 0.0272(13) 0.0370(14) -0.0063(11) 0.0036(11) -0.0007(11)
C3 0.0353(15) 0.0291(14) 0.0575(18) -0.0059(13) 0.0024(13) 0.0010(11)
C4 0.0363(16) 0.0321(14) 0.0514(18) -0.0046(12) -0.0022(13) -0.0023(12)
C5 0.0419(16) 0.0324(15) 0.0396(16) -0.0030(11) 0.0049(12) -0.0039(12)
C6 0.0416(16) 0.0322(15) 0.0356(15) -0.0026(11) 0.0041(12) 0.0049(12)
C7 0.0318(14) 0.0339(14) 0.0351(14) -0.0011(11) 0.0018(11) 0.0041(11)
C8 0.0418(17) 0.0534(19) 0.0346(15) -0.0040(13) 0.0012(12) 0.0054(14)
C9 0.051(2) 0.073(2) 0.0460(19) -0.0136(17) 0.0078(15) 0.0093(17)
C10 0.0427(18) 0.083(3) 0.0443(18) -0.0093(18) -0.0038(14) 0.0020(18)
C11 0.0343(17) 0.127(4) 0.0344(17) 0.0001(19) 0.0057(13) -0.0162(19)
C12 0.0383(17) 0.107(3) 0.0308(16) 0.0019(17) 0.0045(13) -0.0123(18)
C13 0.0346(14) 0.0230(12) 0.0365(15) -0.0032(10) 0.0049(11) -0.0034(10)
C14 0.0344(15) 0.0415(16) 0.0330(14) 0.0040(12) 0.0065(11) 0.0024(12)
C15 0.0391(15) 0.0349(15) 0.0334(15) 0.0041(11) 0.0018(12) 0.0028(12)
C16 0.0349(15) 0.0317(14) 0.0340(13) -0.0001(11) 0.0067(11) 0.0008(11)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C1 1.671(3) . ?
O1 C1 1.330(3) . ?
O1 C8 1.469(4) . ?
N1 C1 1.339(4) . ?
N1 C2 1.426(3) . ?
N1 H1N 0.8800 . ?
N2 C15 1.335(4) . ?
N2 C11 1.337(4) . ?
C2 C7 1.381(4) . ?
C2 C3 1.391(4) . ?
C3 C4 1.381(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.384(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.381(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.388(4) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C10 1.507(4) . ?
C8 C9 1.515(4) . ?
C8 H8 1.0000 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.374(5) . ?
C11 H11 0.9500 . ?
C12 C13 1.388(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.390(4) . ?
C13 C16 1.465(4) . ?
C14 C15 1.384(4) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 C16 1.323(6) 2_756 ?
C16 H16 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
C1 O1 C8 120.0(2) . . ?
C1 N1 C2 127.6(2) . . ?
C1 N1 H1N 116.2 . . ?
C2 N1 H1N 116.2 . . ?
C15 N2 C11 115.9(3) . . ?
O1 C1 N1 112.2(2) . . ?
O1 C1 S1 125.7(2) . . ?
N1 C1 S1 122.0(2) . . ?
C7 C2 C3 119.9(3) . . ?
C7 C2 N1 118.1(2) . . ?
C3 C2 N1 121.8(2) . . ?
C4 C3 C2 119.2(3) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
C3 C4 C5 121.3(3) . . ?
C3 C4 H4 119.3 . . ?
C5 C4 H4 119.3 . . ?
C6 C5 C4 119.0(3) . . ?
C6 C5 H5 120.5 . . ?
C4 C5 H5 120.5 . . ?
C5 C6 C7 120.4(3) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 H6 119.8 . . ?
C2 C7 C6 120.1(3) . . ?
C2 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
O1 C8 C10 105.3(3) . . ?
O1 C8 C9 109.6(3) . . ?
C10 C8 C9 113.2(3) . . ?
O1 C8 H8 109.5 . . ?
C10 C8 H8 109.5 . . ?
C9 C8 H8 109.5 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N2 C11 C12 124.2(3) . . ?
N2 C11 H11 117.9 . . ?
C12 C11 H11 117.9 . . ?
C11 C12 C13 120.0(3) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C12 C13 C14 116.3(3) . . ?
C12 C13 C16 123.9(3) . . ?
C14 C13 C16 119.8(2) . . ?
C15 C14 C13 119.7(2) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
N2 C15 C14 123.9(3) . . ?
N2 C15 H15 118.0 . . ?
C14 C15 H15 118.0 . . ?
C16 C16 C13 125.2(3) 2_756 . ?
C16 C16 H16 117.4 2_756 . ?
C13 C16 H16 117.4 . . ?

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
C8 O1 C1 N1 178.1(2) . . . . ?
C8 O1 C1 S1 -3.4(3) . . . . ?
C2 N1 C1 O1 -1.1(4) . . . . ?
C2 N1 C1 S1 -179.7(2) . . . . ?
C1 N1 C2 C7 135.7(3) . . . . ?
C1 N1 C2 C3 -48.3(4) . . . . ?
C7 C2 C3 C4 -0.9(4) . . . . ?
N1 C2 C3 C4 -176.9(3) . . . . ?
C2 C3 C4 C5 0.0(5) . . . . ?
C3 C4 C5 C6 0.3(4) . . . . ?
C4 C5 C6 C7 0.3(4) . . . . ?
C3 C2 C7 C6 1.5(4) . . . . ?
N1 C2 C7 C6 177.6(2) . . . . ?
C5 C6 C7 C2 -1.2(4) . . . . ?
C1 O1 C8 C10 -154.8(3) . . . . ?
C1 O1 C8 C9 83.1(3) . . . . ?
C15 N2 C11 C12 0.4(6) . . . . ?
N2 C11 C12 C13 0.3(7) . . . . ?
C11 C12 C13 C14 -0.8(5) . . . . ?
C11 C12 C13 C16 178.7(3) . . . . ?
C12 C13 C14 C15 0.7(4) . . . . ?
C16 C13 C14 C15 -178.9(2) . . . . ?
C11 N2 C15 C14 -0.5(5) . . . . ?
C13 C14 C15 N2 -0.1(4) . . . . ?
C12 C13 C16 C16 -9.0(4) . . . 2_756 ?
C14 C13 C16 C16 170.53(18) . . . 2_756 ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.0
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.40
_refine_diff_density_min         -0.41
_refine_diff_density_rms         0.079