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

data_global
_journal_name_full               CrystEngComm

_journal_coden_Cambridge         1350

_publ_contact_author_name        'Maria Gdaniec'
_publ_contact_author_email       MAGDAN@AMU.EDU.PL

_publ_section_title              
;
Strong N-H***N hydrogen bonds and weak N-H***S=C
interactions in controlling structure of co-crystals of dithiooxamide
with nitrogen heterocycles
;
loop_
_publ_author_name
'Maria Gdaniec'
'Barbara Piotrkowska'
'Tadeusz Polonski'
'Aleksandra Wasilewska'

# Attachment 'publ32.cif'

data_dtox-1
_database_code_depnum_ccdc_archive 'CCDC 684402'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
dithioxamide-4,4'-bipyridyl (1/1)
;
_chemical_name_common            "dithioxamide-4,4'-bipyridyl (1/1)"
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H8 N2, C2 H4 N2 S2'
_chemical_formula_sum            'C12 H12 N4 S2'
_chemical_formula_weight         276.38

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

_symmetry_cell_setting           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                   7.5110(5)
_cell_length_b                   8.0199(7)
_cell_length_c                   11.8111(11)
_cell_angle_alpha                109.710(8)
_cell_angle_beta                 93.471(7)
_cell_angle_gamma                99.100(6)
_cell_volume                     656.38(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2455
_cell_measurement_theta_min      3.1
_cell_measurement_theta_max      25

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             288
_exptl_absorpt_coefficient_mu    0.392
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.815
_exptl_absorpt_correction_T_max  0.966
_exptl_absorpt_process_details   'Blessing (1995)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(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  'Kuma KM4CCD κ geometry'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        0
_diffrn_reflns_number            6517
_diffrn_reflns_av_R_equivalents  0.0383
_diffrn_reflns_av_sigmaI/netI    0.0289
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.13
_diffrn_reflns_theta_max         26.37
_reflns_number_total             2671
_reflns_number_gt                2187
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       
;
CrysAlis CCD (Oxford Diffraction, 2006)
;
_computing_cell_refinement       
;
CrysAlis CCD
;
_computing_data_reduction        
;
CrysAlis RED (Oxford Diffraction, 2006)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
; Stereochemical Workstation (Siemens, 1989).
Mercury, Version 1.4
(Macrae et al., 2006)
;
_computing_publication_material  SHELXL-97

_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'

_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)+(0.0677P)²+0.0512P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.008(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2671
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0443
_refine_ls_R_factor_gt           0.0379
_refine_ls_wR_factor_ref         0.1117
_refine_ls_wR_factor_gt          0.1065
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_restrained_S_all      1.092
_refine_ls_shift/su_max          0.002
_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
N1A N 0.96103(18) 0.2245(2) 0.54729(14) 0.0513(4) Uani 1 1 d . . .
C2A C 0.8579(2) 0.1803(3) 0.44228(16) 0.0543(5) Uani 1 1 d . . .
H2A H 0.9093 0.2095 0.3801 0.065 Uiso 1 1 calc R . .
C3A C 0.6785(2) 0.0934(2) 0.42035(15) 0.0474(4) Uani 1 1 d . . .
H3A H 0.6128 0.0658 0.3450 0.057 Uiso 1 1 calc R . .
C4A C 0.59615(19) 0.0473(2) 0.51012(13) 0.0355(3) Uani 1 1 d . . .
C5A C 0.7032(2) 0.0963(3) 0.62004(17) 0.0558(5) Uani 1 1 d . . .
H5A H 0.6551 0.0706 0.6843 0.067 Uiso 1 1 calc R . .
C6A C 0.8812(2) 0.1833(3) 0.63410(18) 0.0594(5) Uani 1 1 d . . .
H6A H 0.9495 0.2151 0.7091 0.071 Uiso 1 1 calc R . .
N1B N 0.94659(18) 0.2609(2) 1.05039(13) 0.0495(4) Uani 1 1 d . . .
C2B C 0.8851(2) 0.1224(3) 0.94803(16) 0.0520(5) Uani 1 1 d . . .
H2B H 0.9626 0.0948 0.8886 0.062 Uiso 1 1 d R . .
C3B C 0.7137(2) 0.0175(2) 0.92473(14) 0.0460(4) Uani 1 1 d . . .
H3B H 0.6785 -0.0777 0.8514 0.055 Uiso 1 1 d R . .
C4B C 0.59324(19) 0.0540(2) 1.01104(13) 0.0344(3) Uani 1 1 d . . .
C5B C 0.6579(2) 0.1976(2) 1.11834(16) 0.0457(4) Uani 1 1 d . . .
H5B H 0.5836 0.2286 1.1794 0.055 Uiso 1 1 calc R . .
C6B C 0.8326(2) 0.2939(2) 1.13402(16) 0.0498(4) Uani 1 1 d . . .
H6B H 0.8731 0.3876 1.2074 0.072(6) Uiso 1 1 calc R . .
S1C S 0.70916(5) 0.60808(6) 0.65386(3) 0.04715(18) Uani 1 1 d . . .
N3C N 0.6668(2) 0.5967(2) 0.42821(12) 0.0431(4) Uani 1 1 d . . .
H3CA H 0.781(3) 0.658(3) 0.4396(17) 0.066(6) Uiso 1 1 d . . .
H3CB H 0.596(3) 0.570(2) 0.3668(17) 0.045(5) Uiso 1 1 d . . .
C2C C 0.59805(19) 0.55319(19) 0.51613(12) 0.0325(3) Uani 1 1 d . . .
S1D S 0.66399(6) 0.70518(6) 1.15736(3) 0.04744(18) Uani 1 1 d . . .
N3D N 0.6936(2) 0.5377(2) 0.92717(13) 0.0490(4) Uani 1 1 d . . .
H3DA H 0.808(4) 0.599(3) 0.9414(19) 0.078(7) Uiso 1 1 d . . .
H3DB H 0.646(3) 0.457(3) 0.8650(17) 0.050(5) Uiso 1 1 d . . .
C2D C 0.59514(19) 0.5602(2) 1.01687(13) 0.0354(3) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1A 0.0297(7) 0.0563(9) 0.0660(9) 0.0245(7) 0.0042(6) -0.0032(6)
C2A 0.0372(9) 0.0684(12) 0.0550(10) 0.0247(9) 0.0129(8) -0.0061(9)
C3A 0.0350(9) 0.0596(11) 0.0414(9) 0.0164(8) 0.0043(7) -0.0056(8)
C4A 0.0285(8) 0.0330(8) 0.0439(8) 0.0136(6) 0.0056(6) 0.0017(6)
C5A 0.0366(9) 0.0779(13) 0.0561(10) 0.0382(9) -0.0019(8) -0.0102(9)
C6A 0.0347(9) 0.0807(14) 0.0622(11) 0.0367(10) -0.0074(8) -0.0116(9)
N1B 0.0316(7) 0.0534(9) 0.0617(9) 0.0238(7) 0.0018(7) -0.0039(6)
C2B 0.0358(9) 0.0671(12) 0.0531(10) 0.0240(9) 0.0131(7) 0.0007(8)
C3B 0.0358(9) 0.0547(10) 0.0412(8) 0.0134(7) 0.0075(7) -0.0022(7)
C4B 0.0294(8) 0.0374(8) 0.0394(8) 0.0187(6) 0.0032(6) 0.0041(6)
C5B 0.0351(9) 0.0470(10) 0.0469(9) 0.0090(7) 0.0080(7) -0.0001(7)
C6B 0.0367(9) 0.0487(10) 0.0525(10) 0.0089(8) 0.0015(7) -0.0040(7)
S1C 0.0364(3) 0.0615(3) 0.0337(2) 0.01294(19) -0.00137(17) -0.0083(2)
N3C 0.0308(8) 0.0570(9) 0.0367(7) 0.0184(6) 0.0027(6) -0.0090(6)
C2C 0.0287(8) 0.0315(7) 0.0327(7) 0.0071(5) 0.0061(6) 0.0013(6)
S1D 0.0384(3) 0.0540(3) 0.0372(2) 0.00901(19) -0.00245(17) -0.00938(19)
N3D 0.0314(8) 0.0677(10) 0.0366(7) 0.0142(7) 0.0019(6) -0.0131(7)
C2D 0.0288(8) 0.0422(8) 0.0353(7) 0.0179(6) -0.0005(6) -0.0011(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
N1A C6A 1.327(2) . ?
N1A C2A 1.328(2) . ?
C2A C3A 1.381(2) . ?
C2A H2A 0.9300 . ?
C3A C4A 1.384(2) . ?
C3A H3A 0.9300 . ?
C4A C5A 1.384(2) . ?
C4A C4A 1.486(3) 2_656 ?
C5A C6A 1.379(2) . ?
C5A H5A 0.9300 . ?
C6A H6A 0.9300 . ?
N1B C2B 1.331(2) . ?
N1B C6B 1.333(2) . ?
C2B C3B 1.379(2) . ?
C2B H2B 0.9300 . ?
C3B C4B 1.392(2) . ?
C3B H3B 0.9300 . ?
C4B C5B 1.390(2) . ?
C4B C4B 1.483(3) 2_657 ?
C5B C6B 1.381(2) . ?
C5B H5B 0.9300 . ?
C6B H6B 0.9300 . ?
S1C C2C 1.6652(14) . ?
N3C C2C 1.3110(19) . ?
N3C H3CA 0.90(2) . ?
N3C H3CB 0.817(19) . ?
C2C C2C 1.536(3) 2_666 ?
S1D C2D 1.6666(15) . ?
N3D C2D 1.308(2) . ?
N3D H3DA 0.89(3) . ?
N3D H3DB 0.813(19) . ?
C2D C2D 1.539(3) 2_667 ?

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
C6A N1A C2A 116.16(14) . . ?
N1A C2A C3A 123.60(16) . . ?
N1A C2A H2A 118.2 . . ?
C3A C2A H2A 118.2 . . ?
C2A C3A C4A 120.27(15) . . ?
C2A C3A H3A 119.9 . . ?
C4A C3A H3A 119.9 . . ?
C5A C4A C3A 115.94(14) . . ?
C5A C4A C4A 122.15(17) . 2_656 ?
C3A C4A C4A 121.91(17) . 2_656 ?
C6A C5A C4A 119.92(16) . . ?
C6A C5A H5A 120.0 . . ?
C4A C5A H5A 120.0 . . ?
N1A C6A C5A 124.10(17) . . ?
N1A C6A H6A 118.0 . . ?
C5A C6A H6A 118.0 . . ?
C2B N1B C6B 116.12(14) . . ?
N1B C2B C3B 123.99(16) . . ?
N1B C2B H2B 118.0 . . ?
C3B C2B H2B 118.0 . . ?
C2B C3B C4B 119.95(15) . . ?
C2B C3B H3B 120.0 . . ?
C4B C3B H3B 120.0 . . ?
C5B C4B C3B 116.08(14) . . ?
C5B C4B C4B 122.23(17) . 2_657 ?
C3B C4B C4B 121.69(17) . 2_657 ?
C6B C5B C4B 119.84(16) . . ?
C6B C5B H5B 120.1 . . ?
C4B C5B H5B 120.1 . . ?
N1B C6B C5B 123.99(16) . . ?
N1B C6B H6B 118.0 . . ?
C5B C6B H6B 118.0 . . ?
C2C N3C H3CA 120.4(13) . . ?
C2C N3C H3CB 115.0(14) . . ?
H3CA N3C H3CB 124.4(19) . . ?
N3C C2C C2C 114.85(15) . 2_666 ?
N3C C2C S1C 124.05(12) . . ?
C2C C2C S1C 121.10(14) 2_666 . ?
C2D N3D H3DA 119.1(14) . . ?
C2D N3D H3DB 113.9(14) . . ?
H3DA N3D H3DB 126(2) . . ?
N3D C2D C2D 114.40(16) . 2_667 ?
N3D C2D S1D 124.40(12) . . ?
C2D C2D S1D 121.20(14) 2_667 . ?

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
N3C H3CA N1A 0.90(2) 1.99(2) 2.883(2) 174.6(19) 2_766
N3C H3CB S1C 0.817(19) 2.454(19) 2.9560(15) 120.7(16) 2_666
N3C H3CB S1D 0.817(19) 3.055(19) 3.5871(15) 125.1(16) 1_554
N3D H3DA N1B 0.89(3) 1.98(3) 2.868(2) 171(2) 2_767
N3D H3DB S1D 0.813(19) 2.433(19) 2.9517(16) 122.6(16) 2_667
N3D H3DB S1C 0.813(19) 3.149(19) 3.4651(15) 106.3(15) .
C3B H3B S1C 0.93 2.85 3.7258(18) 157 1_545

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        26.37
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.257
_refine_diff_density_min         -0.352
_refine_diff_density_rms         0.056

#===END

data_dtox-2
_database_code_depnum_ccdc_archive 'CCDC 684403'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
4,4'-ethane-1,2-diyldipyridine - dithiooxamide (1/1)
;
_chemical_name_common            
"4,4'-ethane-1,2-diyldipyridine - dithiooxamide (1/1)"
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H12 N2, C2 H4 N2 S2'
_chemical_formula_sum            'C14 H16 N4 S2'
_chemical_formula_weight         304.43

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

_symmetry_cell_setting           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                   7.3183(7)
_cell_length_b                   9.4645(12)
_cell_length_c                   11.4992(11)
_cell_angle_alpha                66.910(11)
_cell_angle_beta                 89.531(8)
_cell_angle_gamma                84.021(9)
_cell_volume                     728.22(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    3251
_cell_measurement_theta_min      4.3
_cell_measurement_theta_max      25

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             320
_exptl_absorpt_coefficient_mu    0.361
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.850
_exptl_absorpt_correction_T_max  0.941
_exptl_absorpt_process_details   'Blessing (1995)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      130(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  'Kuma KM4CCD κ geometry'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        0
_diffrn_reflns_number            7619
_diffrn_reflns_av_R_equivalents  0.0236
_diffrn_reflns_av_sigmaI/netI    0.0355
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         4.33
_diffrn_reflns_theta_max         26.37
_reflns_number_total             2962
_reflns_number_gt                2293
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       
;
CrysAlis CCD (Oxford Diffraction, 2006)
;
_computing_cell_refinement       
;
CrysAlis CCD
;
_computing_data_reduction        
;
CrysAlis RED (Oxford Diffraction, 2006)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
; Stereochemical Workstation (Siemens, 1989).
Mercury, Version 1.4
(Macrae et al., 2006)
;
_computing_publication_material  SHELXL-97

_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'

_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)+(0.0705P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2962
_refine_ls_number_parameters     197
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0558
_refine_ls_R_factor_gt           0.0418
_refine_ls_wR_factor_ref         0.1165
_refine_ls_wR_factor_gt          0.1079
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_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
S1A S 0.11308(7) 0.49357(6) 0.67587(5) 0.02490(18) Uani 1 1 d . . .
C2A C 0.0794(3) 0.5313(2) 0.52257(18) 0.0201(4) Uani 1 1 d . . .
N3A N 0.1813(3) 0.6131(2) 0.43261(18) 0.0268(4) Uani 1 1 d . . .
H3AA H 0.144(3) 0.628(3) 0.358(2) 0.038(7) Uiso 1 1 d . . .
H3AB H 0.267(4) 0.654(3) 0.450(2) 0.042(7) Uiso 1 1 d . . .
N1D N 0.4771(2) 0.7622(2) 0.47752(16) 0.0246(4) Uani 1 1 d . . .
C2D C 0.5111(3) 0.7736(2) 0.58718(19) 0.0255(5) Uani 1 1 d . . .
H2D H 0.4249 0.7433 0.6496 0.031 Uiso 1 1 calc R . .
C3D C 0.6679(3) 0.8279(2) 0.61308(19) 0.0228(5) Uani 1 1 d . . .
H3D H 0.6846 0.8347 0.6907 0.027 Uiso 1 1 calc R . .
C4D C 0.8001(3) 0.8724(2) 0.52174(19) 0.0213(4) Uani 1 1 d . . .
C5D C 0.7646(3) 0.8617(2) 0.40729(19) 0.0221(4) Uani 1 1 d . . .
H5D H 0.8485 0.8909 0.3432 0.026 Uiso 1 1 calc R . .
C6D C 0.6031(3) 0.8071(2) 0.3893(2) 0.0237(5) Uani 1 1 d . . .
H6D H 0.5812 0.8013 0.3118 0.028 Uiso 1 1 calc R . .
C7D C 0.9764(3) 0.9245(2) 0.54984(19) 0.0279(5) Uani 1 1 d . . .
H72D H 1.0764 0.8448 0.5587 0.033 Uiso 1 1 calc R . .
H71D H 0.9667 0.9352 0.6302 0.033 Uiso 1 1 calc R . .
S1B S -0.82533(7) 0.94679(6) 0.16674(5) 0.02464(18) Uani 1 1 d . . .
C2B C -0.9135(3) 1.0266(2) 0.01875(18) 0.0192(4) Uani 1 1 d . . .
N3B N -0.8456(2) 1.1389(2) -0.07294(17) 0.0227(4) Uani 1 1 d . . .
H3BA H -0.906(3) 1.174(3) -0.143(2) 0.029(6) Uiso 1 1 d . . .
H3BB H -0.758(4) 1.180(3) -0.060(3) 0.055(9) Uiso 1 1 d . . .
N1C N -0.5250(2) 1.2676(2) -0.03504(16) 0.0245(4) Uani 1 1 d . . .
C2C C -0.4289(3) 1.1960(2) 0.07425(19) 0.0249(5) Uani 1 1 d . . .
H2C H -0.4728 1.1099 0.1356 0.030 Uiso 1 1 calc R . .
C3C C -0.2678(3) 1.2428(2) 0.10111(19) 0.0227(5) Uani 1 1 d . . .
H3C H -0.2070 1.1894 0.1793 0.027 Uiso 1 1 calc R . .
C4C C -0.1964(3) 1.3699(2) 0.01139(19) 0.0206(4) Uani 1 1 d . . .
C5C C -0.2958(3) 1.4439(2) -0.10229(19) 0.0232(5) Uani 1 1 d . . .
H5C H -0.2545 1.5296 -0.1657 0.028 Uiso 1 1 calc R . .
C6C C -0.4568(3) 1.3895(2) -0.1210(2) 0.0261(5) Uani 1 1 d . . .
H6C H -0.5211 1.4411 -0.1980 0.031 Uiso 1 1 calc R . .
C7C C -0.0186(3) 1.4181(2) 0.0416(2) 0.0249(5) Uani 1 1 d . . .
H72C H 0.0821 1.3470 0.0346 0.030 Uiso 1 1 calc R . .
H71C H -0.0192 1.4079 0.1289 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
S1A 0.0248(3) 0.0273(3) 0.0212(3) -0.0066(2) -0.0040(2) -0.0091(2)
C2A 0.0166(10) 0.0178(11) 0.0237(10) -0.0051(9) -0.0048(8) -0.0042(8)
N3A 0.0239(10) 0.0316(11) 0.0219(9) -0.0042(8) -0.0041(8) -0.0161(8)
N1D 0.0187(9) 0.0241(10) 0.0297(10) -0.0075(8) -0.0019(7) -0.0090(7)
C2D 0.0197(10) 0.0273(12) 0.0266(11) -0.0065(10) 0.0031(8) -0.0068(9)
C3D 0.0245(11) 0.0230(11) 0.0204(10) -0.0071(9) -0.0014(8) -0.0061(9)
C4D 0.0196(10) 0.0163(11) 0.0252(10) -0.0041(9) -0.0046(8) -0.0055(8)
C5D 0.0181(10) 0.0246(11) 0.0249(10) -0.0103(9) 0.0016(8) -0.0063(8)
C6D 0.0207(10) 0.0248(12) 0.0287(11) -0.0129(9) -0.0013(8) -0.0056(9)
C7D 0.0264(11) 0.0278(13) 0.0253(11) -0.0035(10) -0.0066(9) -0.0130(10)
S1B 0.0233(3) 0.0307(3) 0.0180(3) -0.0054(2) -0.0030(2) -0.0114(2)
C2B 0.0189(10) 0.0219(11) 0.0187(10) -0.0087(9) 0.0017(8) -0.0074(8)
N3B 0.0209(9) 0.0273(11) 0.0189(9) -0.0054(8) -0.0019(7) -0.0125(8)
N1C 0.0188(9) 0.0254(10) 0.0300(10) -0.0101(8) -0.0006(7) -0.0089(8)
C2C 0.0237(11) 0.0243(12) 0.0258(11) -0.0074(9) 0.0036(8) -0.0094(9)
C3C 0.0206(10) 0.0232(11) 0.0221(10) -0.0058(9) -0.0025(8) -0.0050(9)
C4C 0.0191(10) 0.0209(11) 0.0256(10) -0.0124(9) -0.0008(8) -0.0054(8)
C5C 0.0213(10) 0.0225(11) 0.0236(10) -0.0051(9) -0.0016(8) -0.0087(9)
C6C 0.0192(10) 0.0292(12) 0.0287(11) -0.0093(10) -0.0055(8) -0.0059(9)
C7C 0.0216(11) 0.0253(12) 0.0275(11) -0.0083(10) -0.0045(8) -0.0092(9)

_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
S1A C2A 1.6706(19) . ?
C2A N3A 1.306(3) . ?
C2A C2A 1.538(4) 2_566 ?
N3A H3AA 0.85(3) . ?
N3A H3AB 0.83(3) . ?
N1D C2D 1.335(3) . ?
N1D C6D 1.338(3) . ?
C2D C3D 1.385(3) . ?
C2D H2D 0.9300 . ?
C3D C4D 1.392(3) . ?
C3D H3D 0.9300 . ?
C4D C5D 1.388(3) . ?
C4D C7D 1.508(3) . ?
C5D C6D 1.387(3) . ?
C5D H5D 0.9300 . ?
C6D H6D 0.9300 . ?
C7D C7D 1.513(4) 2_776 ?
C7D H72D 0.9700 . ?
C7D H71D 0.9700 . ?
S1B C2B 1.6707(19) . ?
C2B N3B 1.307(3) . ?
C2B C2B 1.535(4) 2_375 ?
N3B H3BA 0.85(2) . ?
N3B H3BB 0.83(3) . ?
N1C C6C 1.332(3) . ?
N1C C2C 1.334(3) . ?
C2C C3C 1.380(3) . ?
C2C H2C 0.9300 . ?
C3C C4C 1.390(3) . ?
C3C H3C 0.9300 . ?
C4C C5C 1.385(3) . ?
C4C C7C 1.509(3) . ?
C5C C6C 1.384(3) . ?
C5C H5C 0.9300 . ?
C6C H6C 0.9300 . ?
C7C C7C 1.521(4) 2_585 ?
C7C H72C 0.9700 . ?
C7C H71C 0.9700 . ?

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
N3A C2A C2A 114.7(2) . 2_566 ?
N3A C2A S1A 124.50(16) . . ?
C2A C2A S1A 120.81(19) 2_566 . ?
C2A N3A H3AA 114.4(16) . . ?
C2A N3A H3AB 119.9(18) . . ?
H3AA N3A H3AB 125(2) . . ?
C2D N1D C6D 116.91(17) . . ?
N1D C2D C3D 123.60(18) . . ?
N1D C2D H2D 118.2 . . ?
C3D C2D H2D 118.2 . . ?
C2D C3D C4D 119.37(18) . . ?
C2D C3D H3D 120.3 . . ?
C4D C3D H3D 120.3 . . ?
C5D C4D C3D 117.19(18) . . ?
C5D C4D C7D 122.33(18) . . ?
C3D C4D C7D 120.45(18) . . ?
C6D C5D C4D 119.48(18) . . ?
C6D C5D H5D 120.3 . . ?
C4D C5D H5D 120.3 . . ?
N1D C6D C5D 123.44(19) . . ?
N1D C6D H6D 118.3 . . ?
C5D C6D H6D 118.3 . . ?
C4D C7D C7D 114.3(2) . 2_776 ?
C4D C7D H72D 108.7 . . ?
C7D C7D H72D 108.7 2_776 . ?
C4D C7D H71D 108.7 . . ?
C7D C7D H71D 108.7 2_776 . ?
H72D C7D H71D 107.6 . . ?
N3B C2B C2B 114.7(2) . 2_375 ?
N3B C2B S1B 124.01(15) . . ?
C2B C2B S1B 121.30(19) 2_375 . ?
C2B N3B H3BA 115.8(16) . . ?
C2B N3B H3BB 121(2) . . ?
H3BA N3B H3BB 122(2) . . ?
C6C N1C C2C 116.50(17) . . ?
N1C C2C C3C 123.50(19) . . ?
N1C C2C H2C 118.2 . . ?
C3C C2C H2C 118.2 . . ?
C2C C3C C4C 120.02(18) . . ?
C2C C3C H3C 120.0 . . ?
C4C C3C H3C 120.0 . . ?
C5C C4C C3C 116.46(18) . . ?
C5C C4C C7C 124.23(18) . . ?
C3C C4C C7C 119.31(18) . . ?
C6C C5C C4C 119.67(19) . . ?
C6C C5C H5C 120.2 . . ?
C4C C5C H5C 120.2 . . ?
N1C C6C C5C 123.84(19) . . ?
N1C C6C H6C 118.1 . . ?
C5C C6C H6C 118.1 . . ?
C4C C7C C7C 115.3(2) . 2_585 ?
C4C C7C H72C 108.4 . . ?
C7C C7C H72C 108.4 2_585 . ?
C4C C7C H71C 108.4 . . ?
C7C C7C H71C 108.4 2_585 . ?
H72C C7C H71C 107.5 . . ?

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
N3A H3AA S1A 0.85(3) 2.42(2) 2.950(2) 121(2) 2_566
N3A H3AA S1B 0.85(3) 2.99(2) 3.424(2) 114.0(18) 1_655
N3A H3AB N1D 0.83(3) 2.03(3) 2.858(3) 176(2) .
N3B H3BA S1B 0.85(2) 2.45(2) 2.9587(19) 119.6(19) 2_375
N3B H3BA S1A 0.85(2) 2.94(2) 3.450(2) 120.7(18) 1_464
N3B H3BB N1C 0.83(3) 2.04(3) 2.866(2) 174(3) .
C7C H71C S1A 0.97 2.80 3.702(2) 154.2 2_576
C7C H72C N3B 0.97 2.72 3.511(3) 139.7 1_655

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        26.37
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.530
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.066

#===END

data_dtox-3
_database_code_depnum_ccdc_archive 'CCDC 684404'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
dithiooxamide - 2,7-diazapyrene (1/1)
;
_chemical_name_common            'dithiooxamide - 2,7-diazapyrene (1/1)'
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H8 N2, C2 H4 N2 S2'
_chemical_formula_sum            'C16 H12 N4 S2'
_chemical_formula_weight         324.42

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

_symmetry_cell_setting           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                   7.2550(8)
_cell_length_b                   8.7786(12)
_cell_length_c                   11.8824(11)
_cell_angle_alpha                85.341(9)
_cell_angle_beta                 79.117(8)
_cell_angle_gamma                83.618(10)
_cell_volume                     737.15(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    1879
_cell_measurement_theta_min      4
_cell_measurement_theta_max      26

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.462
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             336
_exptl_absorpt_coefficient_mu    0.362
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.864
_exptl_absorpt_correction_T_max  0.981
_exptl_absorpt_process_details   'Blessing (1995)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      130(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  'Kuma KM4CCD κ geometry'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        0
_diffrn_reflns_number            8492
_diffrn_reflns_av_R_equivalents  0.0222
_diffrn_reflns_av_sigmaI/netI    0.0296
_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       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         4.09
_diffrn_reflns_theta_max         26.37
_reflns_number_total             2981
_reflns_number_gt                2231
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       
;
CrysAlis CCD (Oxford Diffraction, 2006)
;
_computing_cell_refinement       
;
CrysAlis CCD
;
_computing_data_reduction        
;
CrysAlis RED (Oxford Diffraction, 2006)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
; Stereochemical Workstation (Siemens, 1989).
Mercury, Version 1.4
(Macrae et al., 2006)
;
_computing_publication_material  SHELXL-97

_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'

_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)+(0.0585P)²P] 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         2981
_refine_ls_number_parameters     215
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0547
_refine_ls_R_factor_gt           0.0370
_refine_ls_wR_factor_ref         0.1045
_refine_ls_wR_factor_gt          0.0964
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_restrained_S_all      1.075
_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
S1A S 0.22479(7) 0.45359(6) 0.09730(4) 0.03224(17) Uani 1 1 d . . .
N3A N 0.4327(2) 0.68612(18) 0.05131(14) 0.0234(4) Uani 1 1 d . . .
H3AA H 0.532(3) 0.724(2) 0.0182(19) 0.038(6) Uiso 1 1 d . . .
H3AB H 0.341(3) 0.742(2) 0.0986(19) 0.039(6) Uiso 1 1 d . . .
C2A C 0.4151(2) 0.5421(2) 0.03790(14) 0.0204(4) Uani 1 1 d . . .
C1D C 0.1996(2) 1.0028(2) 0.25026(16) 0.0272(4) Uani 1 1 d . . .
H1D H 0.2662 1.0645 0.1901 0.033 Uiso 1 1 calc R . .
N1D N 0.1775(2) 0.85920(19) 0.22945(13) 0.0299(4) Uani 1 1 d . . .
C2D C 0.0839(3) 0.7709(2) 0.31348(17) 0.0298(5) Uani 1 1 d . . .
H2D H 0.0665 0.6697 0.2975 0.036 Uiso 1 1 calc R . .
C3D C 0.0102(2) 0.8199(2) 0.42371(16) 0.0249(4) Uani 1 1 d . . .
C4D C -0.0863(3) 0.7247(2) 0.51551(17) 0.0283(5) Uani 1 1 d . . .
H4D H -0.1031 0.6223 0.5022 0.034 Uiso 1 1 calc R . .
C5D C -0.1535(3) 0.7789(2) 0.62078(16) 0.0283(5) Uani 1 1 d . . .
H5D H -0.2170 0.7140 0.6800 0.034 Uiso 1 1 calc R . .
C6D C -0.1301(2) 0.9325(2) 0.64395(15) 0.0238(4) Uani 1 1 d . . .
C7D C 0.0349(2) 0.9715(2) 0.44481(14) 0.0217(4) Uani 1 1 d . . .
S1B S 0.28421(6) 1.03100(5) 0.90907(4) 0.02759(16) Uani 1 1 d . . .
N3B N 0.0485(2) 0.81567(18) 0.94488(14) 0.0234(4) Uani 1 1 d . . .
H3BA H -0.060(3) 0.787(2) 0.9743(18) 0.034(6) Uiso 1 1 d . . .
H3BB H 0.131(3) 0.757(3) 0.8971(19) 0.041(6) Uiso 1 1 d . . .
C2B C 0.0817(2) 0.9547(2) 0.96215(14) 0.0198(4) Uani 1 1 d . . .
C1C C 0.3047(3) 0.4917(2) 0.75089(16) 0.0282(5) Uani 1 1 d . . .
H1C H 0.2622 0.4247 0.8151 0.034 Uiso 1 1 calc R . .
N1C N 0.2725(2) 0.6427(2) 0.76213(14) 0.0319(4) Uani 1 1 d . . .
C2C C 0.3250(3) 0.7389(2) 0.67096(17) 0.0300(5) Uani 1 1 d . . .
H2C H 0.3010 0.8463 0.6800 0.036 Uiso 1 1 calc R . .
C3C C 0.4134(2) 0.6894(2) 0.56307(16) 0.0236(4) Uani 1 1 d . . .
C4C C 0.4675(3) 0.7906(2) 0.46441(17) 0.0285(4) Uani 1 1 d . . .
H4C H 0.4395 0.8983 0.4701 0.034 Uiso 1 1 calc R . .
C5C C 0.5580(3) 0.7356(2) 0.36317(16) 0.0279(5) Uani 1 1 d . . .
H5C H 0.5931 0.8053 0.2992 0.033 Uiso 1 1 calc R . .
C6C C 0.6016(2) 0.5732(2) 0.35115(15) 0.0228(4) Uani 1 1 d . . .
C7C C 0.4527(2) 0.5292(2) 0.55334(14) 0.0203(4) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1A 0.0275(3) 0.0297(3) 0.0364(3) -0.0097(2) 0.0107(2) -0.0122(2)
N3A 0.0223(8) 0.0213(9) 0.0247(9) -0.0038(7) 0.0033(7) -0.0045(7)
C2A 0.0221(9) 0.0229(10) 0.0166(9) -0.0012(7) -0.0032(7) -0.0046(7)
C1D 0.0211(9) 0.0388(12) 0.0210(10) -0.0016(9) -0.0036(7) 0.0001(8)
N1D 0.0244(8) 0.0384(10) 0.0264(9) -0.0079(8) -0.0030(7) 0.0009(7)
C2D 0.0261(10) 0.0336(11) 0.0304(11) -0.0112(9) -0.0040(8) -0.0016(9)
C3D 0.0188(9) 0.0303(11) 0.0260(10) -0.0042(8) -0.0049(7) -0.0013(8)
C4D 0.0261(10) 0.0262(11) 0.0338(12) -0.0051(9) -0.0076(8) -0.0019(8)
C5D 0.0226(9) 0.0339(12) 0.0272(11) 0.0033(9) -0.0034(8) -0.0032(8)
C6D 0.0175(9) 0.0320(11) 0.0214(10) -0.0008(8) -0.0044(7) 0.0011(8)
C7D 0.0150(8) 0.0306(11) 0.0196(9) -0.0038(8) -0.0052(7) 0.0020(7)
S1B 0.0229(3) 0.0267(3) 0.0302(3) -0.0045(2) 0.0072(2) -0.0083(2)
N3B 0.0215(8) 0.0230(9) 0.0245(9) -0.0067(7) 0.0027(7) -0.0045(7)
C2B 0.0210(9) 0.0230(10) 0.0152(9) -0.0003(7) -0.0028(7) -0.0028(7)
C1C 0.0233(10) 0.0400(12) 0.0216(10) -0.0034(9) -0.0025(8) -0.0060(9)
N1C 0.0278(9) 0.0430(11) 0.0252(9) -0.0105(8) -0.0024(7) -0.0034(8)
C2C 0.0259(10) 0.0311(11) 0.0344(12) -0.0121(9) -0.0059(8) 0.0002(8)
C3C 0.0193(9) 0.0257(10) 0.0268(10) -0.0046(8) -0.0055(7) -0.0024(7)
C4C 0.0269(10) 0.0210(10) 0.0387(12) -0.0024(9) -0.0093(9) -0.0016(8)
C5C 0.0270(10) 0.0306(11) 0.0272(11) 0.0039(9) -0.0080(8) -0.0063(8)
C6C 0.0181(9) 0.0294(10) 0.0216(10) -0.0028(8) -0.0040(7) -0.0041(8)
C7C 0.0145(8) 0.0263(10) 0.0210(10) -0.0045(8) -0.0041(7) -0.0029(7)

_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
S1A C2A 1.6704(17) . ?
N3A C2A 1.310(2) . ?
N3A H3AA 0.85(2) . ?
N3A H3AB 0.91(2) . ?
C2A C2A 1.537(3) 2_665 ?
C1D N1D 1.337(2) . ?
C1D C6D 1.404(3) 2_576 ?
C1D H1D 0.9500 . ?
N1D C2D 1.340(2) . ?
C2D C3D 1.401(2) . ?
C2D H2D 0.9500 . ?
C3D C7D 1.412(3) . ?
C3D C4D 1.439(2) . ?
C4D C5D 1.358(3) . ?
C4D H4D 0.9500 . ?
C5D C6D 1.433(3) . ?
C5D H5D 0.9500 . ?
C6D C7D 1.417(2) 2_576 ?
C7D C7D 1.423(3) 2_576 ?
S1B C2B 1.6749(17) . ?
N3B C2B 1.309(2) . ?
N3B H3BA 0.85(2) . ?
N3B H3BB 0.89(2) . ?
C2B C2B 1.534(3) 2_577 ?
C1C N1C 1.333(3) . ?
C1C C6C 1.404(3) 2_666 ?
C1C H1C 0.9500 . ?
N1C C2C 1.341(2) . ?
C2C C3C 1.401(3) . ?
C2C H2C 0.9500 . ?
C3C C7C 1.413(2) . ?
C3C C4C 1.433(2) . ?
C4C C5C 1.355(3) . ?
C4C H4C 0.9500 . ?
C5C C6C 1.438(3) . ?
C5C H5C 0.9500 . ?
C6C C7C 1.413(2) 2_666 ?
C7C C7C 1.428(3) 2_666 ?

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
C2A N3A H3AA 118.9(15) . . ?
C2A N3A H3AB 119.9(14) . . ?
H3AA N3A H3AB 121(2) . . ?
N3A C2A C2A 114.84(19) . 2_665 ?
N3A C2A S1A 123.67(14) . . ?
C2A C2A S1A 121.49(17) 2_665 . ?
N1D C1D C6D 123.67(17) . 2_576 ?
N1D C1D H1D 118.2 . . ?
C6D C1D H1D 118.2 2_576 . ?
C1D N1D C2D 118.82(16) . . ?
N1D C2D C3D 123.47(18) . . ?
N1D C2D H2D 118.3 . . ?
C3D C2D H2D 118.3 . . ?
C2D C3D C7D 117.20(16) . . ?
C2D C3D C4D 123.95(18) . . ?
C7D C3D C4D 118.85(17) . . ?
C5D C4D C3D 121.06(18) . . ?
C5D C4D H4D 119.5 . . ?
C3D C4D H4D 119.5 . . ?
C4D C5D C6D 120.98(17) . . ?
C4D C5D H5D 119.5 . . ?
C6D C5D H5D 119.5 . . ?
C1D C6D C7D 116.82(17) 2_576 2_576 ?
C1D C6D C5D 124.05(17) 2_576 . ?
C7D C6D C5D 119.11(16) 2_576 . ?
C3D C7D C6D 120.00(16) . 2_576 ?
C3D C7D C7D 120.2(2) . 2_576 ?
C6D C7D C7D 119.8(2) 2_576 2_576 ?
C2B N3B H3BA 117.7(14) . . ?
C2B N3B H3BB 120.8(14) . . ?
H3BA N3B H3BB 121(2) . . ?
N3B C2B C2B 114.36(19) . 2_577 ?
N3B C2B S1B 124.32(14) . . ?
C2B C2B S1B 121.32(17) 2_577 . ?
N1C C1C C6C 123.27(17) . 2_666 ?
N1C C1C H1C 118.4 . . ?
C6C C1C H1C 118.4 2_666 . ?
C1C N1C C2C 119.11(17) . . ?
N1C C2C C3C 123.39(18) . . ?
N1C C2C H2C 118.3 . . ?
C3C C2C H2C 118.3 . . ?
C2C C3C C7C 116.93(16) . . ?
C2C C3C C4C 124.06(17) . . ?
C7C C3C C4C 119.00(16) . . ?
C5C C4C C3C 121.23(17) . . ?
C5C C4C H4C 119.4 . . ?
C3C C4C H4C 119.4 . . ?
C4C C5C C6C 120.96(17) . . ?
C4C C5C H5C 119.5 . . ?
C6C C5C H5C 119.5 . . ?
C1C C6C C7C 117.07(17) 2_666 2_666 ?
C1C C6C C5C 123.99(17) 2_666 . ?
C7C C6C C5C 118.94(16) 2_666 . ?
C3C C7C C6C 120.14(16) . 2_666 ?
C3C C7C C7C 119.9(2) . 2_666 ?
C6C C7C C7C 119.9(2) 2_666 2_666 ?

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
N3A H3AA S1A 0.85(2) 2.50(2) 2.9690(17) 115.9(18) 2_665
N3A H3AA S1B 0.85(2) 2.92(2) 3.5065(17) 128.6(18) 2_676
N3A H3AB N1D 0.91(2) 2.04(2) 2.938(2) 167(2) .
N3B H3BA S1B 0.85(2) 2.46(2) 2.9540(18) 117.7(17) 2_577
N3B H3BB N1C 0.89(2) 2.01(2) 2.884(2) 166(2) .
C5D H5D S1A 0.95 2.92 3.7582(19) 148.4 2_566
N3B H3BA S1A 0.85(2) 2.80(2) 3.3734(17) 125.6(17) 2_566
C5C H5C S1B 0.95 2.80 3.7445(19) 171 2_676

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        26.37
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.452
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.053

#===END

data_dtox-4rt
_database_code_depnum_ccdc_archive 'CCDC 684405'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
1,4-diazabicyclo[2.2.2]octane - dithiooxamide (1/1)
;
_chemical_name_common            
'1,4-diazabicyclo(2.2.2)octane - dithiooxamide (1/1)'
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H12 N2, C2 H4 N2 S2'
_chemical_formula_sum            'C8 H16 N4 S2'
_chemical_formula_weight         232.37

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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                   15.7292(7)
_cell_length_b                   6.0827(3)
_cell_length_c                   12.5292(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.511(6)
_cell_angle_gamma                90.00
_cell_volume                     1174.63(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    2454
_cell_measurement_theta_min      4.6
_cell_measurement_theta_max      27

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             496
_exptl_absorpt_coefficient_mu    0.424
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.859
_exptl_absorpt_correction_T_max  0.905
_exptl_absorpt_process_details   'Blessing (1995)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      294(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  'Kuma KM4CCD κ geometry'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        0
_diffrn_reflns_number            5167
_diffrn_reflns_av_R_equivalents  0.0113
_diffrn_reflns_av_sigmaI/netI    0.0119
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         4.64
_diffrn_reflns_theta_max         27.10
_reflns_number_total             1285
_reflns_number_gt                989
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       
;
CrysAlis CCD (Oxford Diffraction, 2006)
;
_computing_cell_refinement       
;
CrysAlis CCD
;
_computing_data_reduction        
;
CrysAlis RED (Oxford Diffraction, 2006)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
; Stereochemical Workstation (Siemens, 1989).
Mercury, Version 1.4
(Macrae et al., 2006)
;
_computing_publication_material  SHELXL-97

_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'

_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)+(0.0570P)²+1.4584P] 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         1285
_refine_ls_number_parameters     72
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0577
_refine_ls_R_factor_gt           0.0442
_refine_ls_wR_factor_ref         0.1256
_refine_ls_wR_factor_gt          0.1139
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_restrained_S_all      1.077
_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 0.33907(4) 0.01219(10) 0.95659(7) 0.0638(3) Uani 1 1 d . . .
C2 C 0.28686(11) 0.2458(3) 0.96782(14) 0.0316(4) Uani 1 1 d . . .
N3 N 0.30372(12) 0.4317(3) 0.92512(16) 0.0424(5) Uani 1 1 d . . .
H3A H 0.3455(19) 0.442(5) 0.887(2) 0.060(7) Uiso 1 1 d . . .
H3B H 0.2767(17) 0.537(4) 0.936(2) 0.049(7) Uiso 1 1 d . . .
N1A N 0.44174(11) 0.4682(3) 0.80859(14) 0.0393(4) Uani 1 1 d . . .
C1A C 0.52000(15) 0.3557(6) 0.86543(19) 0.0582(7) Uani 1 1 d . . .
H1A1 H 0.5053 0.2075 0.8840 0.070 Uiso 1 1 calc R . .
H1A2 H 0.5435 0.4329 0.9326 0.070 Uiso 1 1 calc R . .
C2A C 0.41123(14) 0.3464(5) 0.70655(18) 0.0556(7) Uani 1 1 d . . .
H2A1 H 0.3574 0.4102 0.6676 0.067 Uiso 1 1 calc R . .
H2A2 H 0.4001 0.1945 0.7230 0.067 Uiso 1 1 calc R . .
C3A C 0.4633(2) 0.6914(4) 0.7829(3) 0.0864(12) Uani 1 1 d . . .
H3A1 H 0.4817 0.7738 0.8498 0.104 Uiso 1 1 calc R . .
H3A2 H 0.4123 0.7627 0.7408 0.104 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 0.0641(5) 0.0381(4) 0.1082(6) 0.0130(3) 0.0625(4) 0.0149(3)
C2 0.0281(8) 0.0344(10) 0.0361(9) -0.0001(8) 0.0153(7) 0.0006(7)
N3 0.0436(10) 0.0356(10) 0.0579(11) 0.0068(8) 0.0336(9) 0.0049(8)
N1A 0.0409(9) 0.0390(10) 0.0455(10) 0.0031(7) 0.0267(8) 0.0028(7)
C1A 0.0431(11) 0.091(2) 0.0451(12) 0.0101(13) 0.0193(10) 0.0036(13)
C2A 0.0393(11) 0.0805(19) 0.0510(13) -0.0013(12) 0.0190(10) -0.0058(12)
C3A 0.118(3) 0.0360(13) 0.138(3) -0.0020(15) 0.105(2) 0.0026(15)

_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 C2 1.6610(19) . ?
C2 N3 1.301(3) . ?
C2 C2 1.540(3) 7_557 ?
N3 H3A 0.89(3) . ?
N3 H3B 0.80(3) . ?
N1A C3A 1.451(3) . ?
N1A C1A 1.463(3) . ?
N1A C2A 1.473(3) . ?
C1A C2A 1.541(3) 2_656 ?
C1A H1A1 0.9700 . ?
C1A H1A2 0.9700 . ?
C2A H2A1 0.9700 . ?
C2A H2A2 0.9700 . ?
C3A C3A 1.548(4) 2_656 ?
C3A H3A1 0.9700 . ?
C3A H3A2 0.9700 . ?

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
N3 C2 C2 115.0(2) . 7_557 ?
N3 C2 S1 124.33(14) . . ?
C2 C2 S1 120.65(18) 7_557 . ?
C2 N3 H3A 120.9(19) . . ?
C2 N3 H3B 118.1(19) . . ?
H3A N3 H3B 121(3) . . ?
C3A N1A C1A 109.6(2) . . ?
C3A N1A C2A 109.2(2) . . ?
C1A N1A C2A 106.51(19) . . ?
N1A C1A C2A 110.65(18) . 2_656 ?
N1A C1A H1A1 109.5 . . ?
C2A C1A H1A1 109.5 2_656 . ?
N1A C1A H1A2 109.5 . . ?
C2A C1A H1A2 109.5 2_656 . ?
H1A1 C1A H1A2 108.1 . . ?
N1A C2A C1A 110.15(19) . 2_656 ?
N1A C2A H2A1 109.6 . . ?
C1A C2A H2A1 109.6 2_656 . ?
N1A C2A H2A2 109.6 . . ?
C1A C2A H2A2 109.6 2_656 . ?
H2A1 C2A H2A2 108.1 . . ?
N1A C3A C3A 110.49(11) . 2_656 ?
N1A C3A H3A1 109.6 . . ?
C3A C3A H3A1 109.6 2_656 . ?
N1A C3A H3A2 109.6 . . ?
C3A C3A H3A2 109.6 2_656 . ?
H3A1 C3A H3A2 108.1 . . ?

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
C3A N1A C1A C2A -60.4(3) . . . 2_656 ?
C2A N1A C1A C2A 57.5(2) . . . 2_656 ?
C3A N1A C2A C1A 55.8(3) . . . 2_656 ?
C1A N1A C2A C1A -62.4(2) . . . 2_656 ?
C1A N1A C3A C3A 55.3(5) . . . 2_656 ?
C2A N1A C3A C3A -61.0(5) . . . 2_656 ?
N1A C3A C3A N1A 4.9(6) . . 2_656 2_656 ?
N1A C2A C1A N1A 4.2(3) . . 2_656 2_656 ?

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
N3 H3A N1A 0.89(3) 1.97(3) 2.856(2) 178(3) .
N3 H3B S1 0.80(3) 2.49(3) 2.9471(18) 118(2) 7_557
N3 H3B S1 0.80(3) 3.05(3) 3.584(2) 127(2) 1_565

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        27.10
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.389
_refine_diff_density_min         -0.390
_refine_diff_density_rms         0.056

#===END

_vrf_PLAT029_dtox-4lt            
;
PROBLEM: _diffrn_measured_fraction_theta_full Low ....... 0.89
RESPONSE: The low data completness is due to the crystal twinning
because 257 partially overlapping reflections were removed from
the data set.
;

data_dtox-4(lt)
_database_code_depnum_ccdc_archive 'CCDC 684406'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
1,4-diazabicyclo[2.2.2]octane - dithiooxamide (1/1)
;
_chemical_name_common            
'1,4-diazabicyclo(2.2.2)octane - dithiooxamide (1/1)'
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H12 N2, C2 H4 N2 S2'
_chemical_formula_sum            'C8 H16 N4 S2'
_chemical_formula_weight         232.37

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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                   6.0414(8)
_cell_length_b                   8.3514(4)
_cell_length_c                   12.3639(6)
_cell_angle_alpha                77.833(4)
_cell_angle_beta                 88.565(8)
_cell_angle_gamma                69.780(8)
_cell_volume                     571.44(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    140(2)
_cell_measurement_reflns_used    3188
_cell_measurement_theta_min      4
_cell_measurement_theta_max      26

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             248
_exptl_absorpt_coefficient_mu    0.436
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.812
_exptl_absorpt_correction_T_max  0.881
_exptl_absorpt_process_details   'Blessing (1995)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      140(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  'Kuma KM4CCD κ geometry'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_reflns_number            8961
_diffrn_reflns_av_R_equivalents  0.0356
_diffrn_reflns_av_sigmaI/netI    0.0219
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         4.19
_diffrn_reflns_theta_max         26.37
_reflns_number_total             2090
_reflns_number_gt                1827
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       
;
CrysAlis CCD (Oxford Diffraction, 2006)
;
_computing_cell_refinement       
;
CrysAlis CCD
;
_computing_data_reduction        
;
CrysAlis RED (Oxford Diffraction, 2006)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
; Stereochemical Workstation (Siemens, 1989).
Mercury, Version 1.4
(Macrae et al., 2006)
;
_computing_publication_material  SHELXL-97

_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'

_refine_special_details          
; The crystal exhibits non-merohedral twinning corresponding to
180 degree rotation about
2 1 0 reciprocal lattice direction.
'HKLF 5' instruction of SHELXL has been used during the refinement.
The BASF parameter refined at 0.390(3).
A group of 257 reflections has been removed from the refinement process
(the cause of low completness of 89% )because these
reflections were 'partial overlapps' an could not be properly integrated
during data processing.

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)+(0.0873P)²+0.2318P] 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         2090
_refine_ls_number_parameters     144
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0506
_refine_ls_R_factor_gt           0.0439
_refine_ls_wR_factor_ref         0.1443
_refine_ls_wR_factor_gt          0.1307
_refine_ls_goodness_of_fit_ref   1.152
_refine_ls_restrained_S_all      1.152
_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
S1A S 0.17265(13) 0.19389(9) 0.53106(6) 0.0290(2) Uani 1 1 d . . .
C2A C 0.4582(5) 0.0756(3) 0.53114(17) 0.0171(5) Uani 1 1 d . . .
N3A N 0.6282(4) 0.1016(3) 0.58107(17) 0.0201(5) Uani 1 1 d . . .
H3AA H 0.596(7) 0.184(5) 0.618(3) 0.038(9) Uiso 1 1 d . . .
H3AB H 0.766(8) 0.037(5) 0.577(3) 0.032(9) Uiso 1 1 d . . .
S1B S -0.16015(12) 0.83397(9) 0.94415(6) 0.0280(2) Uani 1 1 d . . .
C2B C 0.0320(4) 0.9289(3) 0.96560(17) 0.0146(5) Uani 1 1 d . . .
N3B N 0.2430(4) 0.8907(3) 0.92733(17) 0.0204(5) Uani 1 1 d . . .
H3BA H 0.293(7) 0.807(5) 0.892(3) 0.034(9) Uiso 1 1 d . . .
H3BB H 0.326(8) 0.943(5) 0.945(3) 0.036(9) Uiso 1 1 d . . .
N1 N 0.5257(4) 0.3795(3) 0.69483(16) 0.0192(5) Uani 1 1 d . . .
N2 N 0.4159(4) 0.6150(3) 0.81181(16) 0.0192(5) Uani 1 1 d . . .
C1 C 0.3600(6) 0.5453(3) 0.6308(2) 0.0296(7) Uani 1 1 d . . .
H1A H 0.2259 0.5275 0.6023 0.036 Uiso 1 1 d R . .
H1B H 0.4405 0.5871 0.5690 0.036 Uiso 1 1 d R . .
C2 C 0.2793(6) 0.6826(3) 0.7042(2) 0.0269(6) Uani 1 1 d . . .
H2A H 0.3024 0.7888 0.6672 0.032 Uiso 1 1 d R . .
H2B H 0.1139 0.7084 0.7159 0.032 Uiso 1 1 d R . .
C3 C 0.7393(6) 0.4082(4) 0.7284(3) 0.0341(7) Uani 1 1 d . . .
H3A H 0.8209 0.4384 0.6636 0.041 Uiso 1 1 d R . .
H3B H 0.8433 0.3027 0.7746 0.041 Uiso 1 1 d R . .
C4 C 0.6687(6) 0.5596(4) 0.7919(3) 0.0348(7) Uani 1 1 d . . .
H4A H 0.7569 0.5198 0.8618 0.042 Uiso 1 1 d R . .
H4B H 0.7071 0.6568 0.7501 0.042 Uiso 1 1 d R . .
C5 C 0.4119(5) 0.3244(3) 0.7959(2) 0.0226(6) Uani 1 1 d . . .
H5A H 0.5121 0.2120 0.8363 0.027 Uiso 1 1 d R . .
H5B H 0.2656 0.3143 0.7759 0.027 Uiso 1 1 d R . .
C6 C 0.3606(5) 0.4608(3) 0.86994(19) 0.0236(6) Uani 1 1 d . . .
H6A H 0.1978 0.4956 0.8887 0.028 Uiso 1 1 d R . .
H6B H 0.4563 0.4083 0.9376 0.028 Uiso 1 1 d 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
S1A 0.0171(4) 0.0275(4) 0.0463(4) -0.0264(3) 0.0022(3) -0.0018(3)
C2A 0.0209(14) 0.0151(10) 0.0173(10) -0.0084(9) 0.0034(9) -0.0062(10)
N3A 0.0157(12) 0.0194(10) 0.0275(10) -0.0163(9) 0.0019(8) -0.0026(9)
S1B 0.0200(4) 0.0304(4) 0.0478(4) -0.0300(3) 0.0126(3) -0.0144(3)
C2B 0.0144(13) 0.0142(10) 0.0166(10) -0.0070(8) 0.0007(8) -0.0044(9)
N3B 0.0176(12) 0.0209(10) 0.0296(11) -0.0179(9) 0.0071(8) -0.0084(9)
N1 0.0176(12) 0.0198(9) 0.0235(10) -0.0138(8) 0.0037(8) -0.0054(9)
N2 0.0204(12) 0.0204(9) 0.0225(9) -0.0146(8) 0.0059(8) -0.0085(9)
C1 0.0470(19) 0.0187(11) 0.0205(11) -0.0096(10) 0.0001(11) -0.0047(12)
C2 0.0394(18) 0.0174(11) 0.0214(11) -0.0088(9) 0.0034(11) -0.0041(11)
C3 0.0209(16) 0.0425(16) 0.0533(17) -0.0383(14) 0.0139(12) -0.0135(13)
C4 0.0214(16) 0.0476(17) 0.0524(17) -0.0387(14) 0.0129(12) -0.0175(13)
C5 0.0276(15) 0.0192(11) 0.0245(11) -0.0106(9) 0.0029(10) -0.0089(11)
C6 0.0312(16) 0.0196(11) 0.0209(11) -0.0093(9) 0.0062(10) -0.0073(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
S1A C2A 1.665(3) . ?
C2A N3A 1.313(3) . ?
C2A C2A 1.546(4) 2_656 ?
N3A H3AA 0.87(4) . ?
N3A H3AB 0.83(4) . ?
S1B C2B 1.669(2) . ?
C2B N3B 1.305(3) . ?
C2B C2B 1.541(4) 2_577 ?
N3B H3BA 0.86(4) . ?
N3B H3BB 0.83(4) . ?
N1 C1 1.472(3) . ?
N1 C3 1.475(4) . ?
N1 C5 1.476(3) . ?
N2 C4 1.466(4) . ?
N2 C6 1.477(3) . ?
N2 C2 1.479(3) . ?
C1 C2 1.551(3) . ?
C1 H1A 0.9603 . ?
C1 H1B 0.9640 . ?
C2 H2A 0.9627 . ?
C2 H2B 0.9612 . ?
C3 C4 1.557(3) . ?
C3 H3A 0.9639 . ?
C3 H3B 0.9598 . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9632 . ?
C5 C6 1.553(3) . ?
C5 H5A 0.9599 . ?
C5 H5B 0.9605 . ?
C6 H6A 0.9614 . ?
C6 H6B 0.9599 . ?

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
N3A C2A C2A 114.8(3) . 2_656 ?
N3A C2A S1A 124.35(18) . . ?
C2A C2A S1A 120.8(2) 2_656 . ?
C2A N3A H3AA 121(3) . . ?
C2A N3A H3AB 118(3) . . ?
H3AA N3A H3AB 121(4) . . ?
N3B C2B C2B 115.1(3) . 2_577 ?
N3B C2B S1B 124.08(18) . . ?
C2B C2B S1B 120.9(2) 2_577 . ?
C2B N3B H3BA 119(3) . . ?
C2B N3B H3BB 116(3) . . ?
H3BA N3B H3BB 124(4) . . ?
C1 N1 C3 109.0(2) . . ?
C1 N1 C5 108.3(2) . . ?
C3 N1 C5 108.3(2) . . ?
C4 N2 C6 108.6(2) . . ?
C4 N2 C2 109.1(2) . . ?
C6 N2 C2 107.7(2) . . ?
N1 C1 C2 110.22(19) . . ?
N1 C1 H1A 110.5 . . ?
C2 C1 H1A 110.4 . . ?
N1 C1 H1B 108.1 . . ?
C2 C1 H1B 109.2 . . ?
H1A C1 H1B 108.3 . . ?
N2 C2 C1 110.3(2) . . ?
N2 C2 H2A 109.3 . . ?
C1 C2 H2A 109.9 . . ?
N2 C2 H2B 109.9 . . ?
C1 C2 H2B 109.0 . . ?
H2A C2 H2B 108.4 . . ?
N1 C3 C4 109.8(2) . . ?
N1 C3 H3A 109.7 . . ?
C4 C3 H3A 109.3 . . ?
N1 C3 H3B 109.5 . . ?
C4 C3 H3B 110.2 . . ?
H3A C3 H3B 108.3 . . ?
N2 C4 C3 110.6(2) . . ?
N2 C4 H4A 108.9 . . ?
C3 C4 H4A 109.1 . . ?
N2 C4 H4B 110.1 . . ?
C3 C4 H4B 109.9 . . ?
H4A C4 H4B 108.1 . . ?
N1 C5 C6 110.4(2) . . ?
N1 C5 H5A 109.8 . . ?
C6 C5 H5A 110.1 . . ?
N1 C5 H5B 109.6 . . ?
C6 C5 H5B 108.9 . . ?
H5A C5 H5B 108.0 . . ?
N2 C6 C5 110.08(19) . . ?
N2 C6 H6A 110.0 . . ?
C5 C6 H6A 110.2 . . ?
N2 C6 H6B 109.6 . . ?
C5 C6 H6B 109.0 . . ?
H6A C6 H6B 107.8 . . ?

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
C3 N1 C1 C2 -63.0(3) . . . . ?
C5 N1 C1 C2 54.7(3) . . . . ?
C4 N2 C2 C1 54.0(3) . . . . ?
C6 N2 C2 C1 -63.7(3) . . . . ?
N1 C1 C2 N2 7.5(3) . . . . ?
C1 N1 C3 C4 54.8(3) . . . . ?
C5 N1 C3 C4 -62.9(3) . . . . ?
C6 N2 C4 C3 54.9(3) . . . . ?
C2 N2 C4 C3 -62.2(3) . . . . ?
N1 C3 C4 N2 6.9(4) . . . . ?
C1 N1 C5 C6 -62.7(3) . . . . ?
C3 N1 C5 C6 55.4(3) . . . . ?
C4 N2 C6 C5 -62.4(3) . . . . ?
C2 N2 C6 C5 55.6(3) . . . . ?
N1 C5 C6 N2 6.3(3) . . . . ?

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
N3A H3AA N1 0.87(4) 1.98(4) 2.844(3) 177(3) .
N3B H3BA N2 0.86(4) 1.98(4) 2.843(3) 179(4) .
N3A H3AB S1A 0.83(4) 2.49(4) 2.960(2) 117(3) 2_656
N3A H3AB S1A 0.83(4) 3.15(4) 3.640(3) 121(3) 1_655
N3B H3BB S1B 0.83(4) 2.46(4) 2.961(2) 119(3) 2_577
N3B H3BB S1B 0.83(4) 2.92(4) 3.477(3) 127(3) 1_655

_diffrn_measured_fraction_theta_max 0.889
_diffrn_reflns_theta_full        26.37
_diffrn_measured_fraction_theta_full 0.889
_refine_diff_density_max         0.568
_refine_diff_density_min         -0.379
_refine_diff_density_rms         0.082

#===END

data_dtox-5
_database_code_depnum_ccdc_archive 'CCDC 684407'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
1,3,5,7-tetraazatricyclo[3.3.1.13,7]decane - dithiooxamide
(1/1)
;
_chemical_name_common            
;1,3,5,7-tetraazatricyclo(3.3.1.13,7)decane - dithiooxamide
(1/1)
;
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H12 N4, C2 H4 N2 S2'
_chemical_formula_sum            'C8 H16 N6 S2'
_chemical_formula_weight         260.39

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'
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                   9.7776(10)
_cell_length_b                   7.3250(7)
_cell_length_c                   17.6664(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.485(8)
_cell_angle_gamma                90.00
_cell_volume                     1225.06(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    2872
_cell_measurement_theta_min      4.8
_cell_measurement_theta_max      25

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             552
_exptl_absorpt_coefficient_mu    0.419
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8503
_exptl_absorpt_correction_T_max  0.9398
_exptl_absorpt_process_details   'Blessing (1995)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      130(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  'Kuma KM4CCD κ geometry'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        0
_diffrn_reflns_number            3310
_diffrn_reflns_av_R_equivalents  0.0175
_diffrn_reflns_av_sigmaI/netI    0.0199
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         4.77
_diffrn_reflns_theta_max         26.36
_reflns_number_total             1233
_reflns_number_gt                1070
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       
;
CrysAlis CCD (Oxford Diffraction, 2006)
;
_computing_cell_refinement       
;
CrysAlis CCD
;
_computing_data_reduction        
;
CrysAlis RED (Oxford Diffraction, 2006)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
; Stereochemical Workstation (Siemens, 1989).
Mercury, Version 1.4
(Macrae et al., 2006)
;
_computing_publication_material  SHELXL-97

_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'

_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)+(0.0505P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1233
_refine_ls_number_parameters     82
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0309
_refine_ls_R_factor_gt           0.0263
_refine_ls_wR_factor_ref         0.0756
_refine_ls_wR_factor_gt          0.0733
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_restrained_S_all      1.105
_refine_ls_shift/su_max          0.002
_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
N1A N 0.37038(11) 0.66195(14) 0.72745(6) 0.0182(3) Uani 1 1 d . . .
C2A C 0.36559(15) 0.54448(18) 0.79428(8) 0.0212(3) Uani 1 1 d . . .
H21A H 0.2798 0.4675 0.7803 0.025 Uiso 1 1 calc R . .
H22A H 0.3590 0.6221 0.8391 0.025 Uiso 1 1 calc R . .
C3A C 0.5000 0.7734(2) 0.7500 0.0184(4) Uani 1 2 d S . .
H3C H 0.5061 0.8494 0.7067 0.022 Uiso 1 1 d R . .
C4A C 0.38135(14) 0.54329(19) 0.66196(8) 0.0211(3) Uani 1 1 d . . .
H41A H 0.3850 0.6201 0.6164 0.025 Uiso 1 1 calc R . .
H42A H 0.2959 0.4658 0.6469 0.025 Uiso 1 1 calc R . .
N5A N 0.50807(11) 0.42502(15) 0.68198(6) 0.0185(3) Uani 1 1 d . . .
C6A C 0.5000 0.3124(2) 0.7500 0.0183(4) Uani 1 2 d S . .
H6A H 0.4190 0.2342 0.7348 0.022 Uiso 1 1 d R . .
S1 S 0.32489(3) 0.01141(4) 0.555328(19) 0.02089(15) Uani 1 1 d . . .
C2 C 0.47413(13) 0.06028(17) 0.52924(7) 0.0157(3) Uani 1 1 d . . .
N3 N 0.55498(13) 0.20064(16) 0.55555(7) 0.0232(3) Uani 1 1 d . . .
H3A H 0.5342(17) 0.272(3) 0.5888(11) 0.040(5) Uiso 1 1 d . . .
H3B H 0.6300(18) 0.222(2) 0.5398(9) 0.031(4) Uiso 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1A 0.0172(5) 0.0152(5) 0.0223(6) 0.0013(4) 0.0053(4) 0.0020(4)
C2A 0.0192(7) 0.0206(6) 0.0282(8) 0.0031(5) 0.0140(6) 0.0022(5)
C3A 0.0230(9) 0.0127(8) 0.0204(9) 0.000 0.0070(7) 0.000
C4A 0.0215(7) 0.0200(7) 0.0188(7) 0.0004(5) -0.0009(5) 0.0001(5)
N5A 0.0219(6) 0.0158(5) 0.0187(6) -0.0041(4) 0.0066(5) -0.0019(4)
C6A 0.0173(9) 0.0124(8) 0.0249(9) 0.000 0.0047(7) 0.000
S1 0.0214(2) 0.0211(2) 0.0247(2) -0.00495(13) 0.01420(15) -0.00377(12)
C2 0.0185(6) 0.0158(6) 0.0133(6) 0.0003(5) 0.0046(5) 0.0017(5)
N3 0.0233(6) 0.0222(6) 0.0279(7) -0.0126(5) 0.0136(5) -0.0072(5)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1A C2A 1.4711(16) . ?
N1A C4A 1.4722(17) . ?
N1A C3A 1.4761(14) . ?
C2A N5A 1.4861(17) 2_656 ?
C2A H21A 0.9900 . ?
C2A H22A 0.9900 . ?
C3A H3C 0.9601 . ?
C4A N5A 1.4804(18) . ?
C4A H41A 0.9900 . ?
C4A H42A 0.9900 . ?
N5A C6A 1.4758(14) . ?
C6A H6A 0.9600 . ?
S1 C2 1.6752(13) . ?
C2 N3 1.3092(17) . ?
C2 C2 1.538(2) 5_656 ?
N3 H3A 0.847(19) . ?
N3 H3B 0.861(18) . ?

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
C2A N1A C4A 107.97(10) . . ?
C2A N1A C3A 107.72(9) . . ?
C4A N1A C3A 108.19(9) . . ?
N1A C2A N5A 112.32(10) . 2_656 ?
N1A C2A H21A 109.1 . . ?
N5A C2A H21A 109.1 2_656 . ?
N1A C2A H22A 109.1 . . ?
N5A C2A H22A 109.1 2_656 . ?
H21A C2A H22A 107.9 . . ?
N1A C3A N1A 112.85(14) 2_656 . ?
N1A C3A H3C 108.4 2_656 . ?
N1A C3A H3C 109.0 . . ?
N1A C4A N5A 112.27(10) . . ?
N1A C4A H41A 109.2 . . ?
N5A C4A H41A 109.2 . . ?
N1A C4A H42A 109.2 . . ?
N5A C4A H42A 109.2 . . ?
H41A C4A H42A 107.9 . . ?
C6A N5A C4A 108.03(9) . . ?
C6A N5A C2A 108.01(9) . 2_656 ?
C4A N5A C2A 108.05(10) . 2_656 ?
N5A C6A N5A 112.05(14) . 2_656 ?
N5A C6A H6A 108.3 . . ?
N5A C6A H6A 110.7 2_656 . ?
N3 C2 C2 114.75(14) . 5_656 ?
N3 C2 S1 124.08(10) . . ?
C2 C2 S1 121.18(12) 5_656 . ?
C2 N3 H3A 120.1(12) . . ?
C2 N3 H3B 120.9(11) . . ?
H3A N3 H3B 119.1(16) . . ?

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
N3 H3A N5A 0.847(19) 2.06(2) 2.9005(16) 171.2(16) .
N3 H3B S1 0.861(18) 2.510(17) 2.9631(13) 113.7(13) 5_656
N3 H3B S1 0.861(18) 2.820(17) 3.4859(13) 135.4(14) 3

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        26.36
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         0.311
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.050

#===END

data_dtox-6
_database_code_depnum_ccdc_archive 'CCDC 684408'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
dithiooxamide-1,10-phenanthroline (1/1)
;
_chemical_name_common            'dithiooxamide-1,10-phenanthroline (1/1)'
_chemical_melting_point          ?
_chemical_formula_moiety         'C2 H4 N2 S2, 2(C12 H8 N2)'
_chemical_formula_sum            'C26 H20 N6 S2'
_chemical_formula_weight         480.60

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

_symmetry_cell_setting           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                   10.7438(9)
_cell_length_b                   10.0220(9)
_cell_length_c                   10.9457(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.110(7)
_cell_angle_gamma                90.00
_cell_volume                     1171.88(18)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2354
_cell_measurement_theta_min      3.2
_cell_measurement_theta_max      25.0

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.40
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             500
_exptl_absorpt_coefficient_mu    0.255
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8832
_exptl_absorpt_correction_T_max  0.9049
_exptl_absorpt_process_details   'Blessing (1995)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(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  'Kuma KM4CCD κ geometry'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        0
_diffrn_reflns_number            6999
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_av_sigmaI/netI    0.0224
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.24
_diffrn_reflns_theta_max         25.02
_reflns_number_total             2064
_reflns_number_gt                1647
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlis CCD (Oxford Diffraction, 2006)
;
_computing_cell_refinement       
;
CrysAlis CCD
;
_computing_data_reduction        
;
CrysAlis RED (Oxford Diffraction, 2006)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
; Stereochemical Workstation (Siemens, 1989).
Mercury, Version 1.4
(Macrae et al., 2006)
;
_computing_publication_material  SHELXL-97

_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'

_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)+(0.0850P)²+0.1893P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.011(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2064
_refine_ls_number_parameters     174
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0575
_refine_ls_R_factor_gt           0.0487
_refine_ls_wR_factor_ref         0.1467
_refine_ls_wR_factor_gt          0.1359
_refine_ls_goodness_of_fit_ref   1.122
_refine_ls_restrained_S_all      1.121
_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
N1A N 0.30395(18) 0.5463(2) 0.35982(17) 0.0629(5) Uani 1 1 d . . .
C2A C 0.2204(3) 0.4526(3) 0.3740(3) 0.0817(8) Uani 1 1 d . . .
H2A H 0.1830 0.4107 0.3037 0.098 Uiso 1 1 calc R . .
C3A C 0.1843(3) 0.4119(3) 0.4870(3) 0.0880(9) Uani 1 1 d . . .
H3C H 0.1236 0.3463 0.4910 0.106 Uiso 1 1 calc R . .
C4A C 0.2390(3) 0.4696(3) 0.5902(3) 0.0779(8) Uani 1 1 d . . .
H4A H 0.2175 0.4432 0.6666 0.093 Uiso 1 1 calc R . .
C5A C 0.3885(2) 0.6375(3) 0.6873(2) 0.0745(8) Uani 1 1 d . . .
H5A H 0.3661 0.6161 0.7648 0.089 Uiso 1 1 calc R . .
C6A C 0.4753(2) 0.7300(3) 0.6772(2) 0.0766(8) Uani 1 1 d . . .
H6A H 0.5149 0.7726 0.7497 0.092 Uiso 1 1 d R . .
C7A C 0.6032(2) 0.8632(3) 0.5461(2) 0.0735(8) Uani 1 1 d . . .
H7A H 0.6449 0.9057 0.6177 0.088 Uiso 1 1 d R . .
C8A C 0.6322(2) 0.8959(3) 0.4318(2) 0.0711(7) Uani 1 1 d . . .
H8A H 0.6950 0.9616 0.4204 0.085 Uiso 1 1 d R . .
C9A C 0.5705(2) 0.8310(2) 0.3317(2) 0.0611(6) Uani 1 1 d . . .
H9A H 0.5901 0.8544 0.2509 0.073 Uiso 1 1 d R . .
N10A N 0.48331(16) 0.73881(18) 0.33978(15) 0.0526(5) Uani 1 1 d . . .
C11A C 0.45242(17) 0.7061(2) 0.45259(17) 0.0459(5) Uani 1 1 d . . .
C12A C 0.51114(19) 0.7669(2) 0.55982(19) 0.0576(6) Uani 1 1 d . . .
C13A C 0.35903(18) 0.6047(2) 0.46357(18) 0.0487(5) Uani 1 1 d . . .
C14A C 0.3284(2) 0.5695(2) 0.5814(2) 0.0587(6) Uani 1 1 d . . .
S1 S 0.61439(7) 0.67735(8) 0.02422(10) 0.0640(4) Uani 0.937(4) 1 d P . .
N3 N 0.4321(2) 0.5616(3) 0.1286(2) 0.0547(8) Uani 0.937(4) 1 d P . .
H3A H 0.384(2) 0.493(3) 0.132(2) 0.061(7) Uiso 0.937(4) 1 d P . .
H3B H 0.437(2) 0.620(3) 0.187(2) 0.064(7) Uiso 0.937(4) 1 d P . .
C2 C 0.50800(18) 0.5602(2) 0.04317(17) 0.0461(6) Uani 0.937(4) 1 d P . .
S1B S 0.6400(10) 0.6510(12) -0.0248(15) 0.064(4) Uiso 0.063(4) 1 d PD A 2
C2B C 0.5464(18) 0.5182(18) -0.0460(13) 0.064(4) Uiso 0.063(4) 1 d PD . 2
N3B N 0.541(5) 0.439(5) -0.140(4) 0.064(4) Uiso 0.063(4) 1 d PD . 2
H3BA H 0.5913 0.4547 -0.1992 0.064(4) Uiso 0.063(4) 1 d PR A 2
H3BB H 0.4884 0.3695 -0.1458 0.064(4) Uiso 0.063(4) 1 d PR A 2

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
N1A 0.0642(12) 0.0594(12) 0.0667(12) -0.0043(9) 0.0147(9) -0.0106(9)
C2A 0.0813(17) 0.0712(18) 0.0952(19) -0.0111(14) 0.0211(15) -0.0200(14)
C3A 0.0857(18) 0.0603(17) 0.126(3) 0.0060(16) 0.0502(18) -0.0109(14)
C4A 0.0808(17) 0.0653(16) 0.095(2) 0.0221(14) 0.0428(15) 0.0172(14)
C5A 0.0679(15) 0.110(2) 0.0477(12) 0.0169(13) 0.0137(11) 0.0283(15)
C6A 0.0615(14) 0.119(2) 0.0482(12) -0.0050(13) 0.0019(10) 0.0131(15)
C7A 0.0564(14) 0.0870(19) 0.0754(16) -0.0294(14) -0.0006(12) -0.0013(13)
C8A 0.0573(13) 0.0703(17) 0.0865(17) -0.0178(13) 0.0121(12) -0.0137(12)
C9A 0.0610(13) 0.0579(14) 0.0657(14) -0.0016(10) 0.0121(11) -0.0074(11)
N10A 0.0555(10) 0.0526(11) 0.0503(10) -0.0020(8) 0.0079(7) -0.0038(8)
C11A 0.0437(10) 0.0477(12) 0.0466(10) 0.0001(8) 0.0060(8) 0.0117(8)
C12A 0.0490(12) 0.0714(15) 0.0510(12) -0.0070(10) -0.0004(9) 0.0129(11)
C13A 0.0481(10) 0.0472(12) 0.0521(11) 0.0035(9) 0.0113(8) 0.0113(9)
C14A 0.0539(12) 0.0615(14) 0.0638(13) 0.0141(11) 0.0201(10) 0.0221(11)
S1 0.0645(5) 0.0568(5) 0.0727(6) -0.0106(3) 0.0162(4) -0.0170(3)
N3 0.0589(18) 0.0565(13) 0.0499(12) -0.0089(10) 0.0116(12) -0.0073(13)
C2 0.0449(11) 0.0486(13) 0.0437(11) 0.0001(9) 0.0003(8) 0.0019(9)

_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
N1A C2A 1.320(3) . ?
N1A C13A 1.356(3) . ?
C2A C3A 1.397(4) . ?
C2A H2A 0.9300 . ?
C3A C4A 1.347(4) . ?
C3A H3C 0.9300 . ?
C4A C14A 1.397(4) . ?
C4A H4A 0.9300 . ?
C5A C6A 1.328(4) . ?
C5A C14A 1.438(4) . ?
C5A H5A 0.9300 . ?
C6A C12A 1.428(3) . ?
C6A H6A 0.9600 . ?
C7A C8A 1.361(4) . ?
C7A C12A 1.401(4) . ?
C7A H7A 0.9600 . ?
C8A C9A 1.382(3) . ?
C8A H8A 0.9600 . ?
C9A N10A 1.325(3) . ?
C9A H9A 0.9599 . ?
N10A C11A 1.353(3) . ?
C11A C12A 1.411(3) . ?
C11A C13A 1.442(3) . ?
C13A C14A 1.409(3) . ?
S1 C2 1.667(2) . ?
N3 C2 1.305(3) . ?
N3 H3A 0.86(3) . ?
N3 H3B 0.87(3) . ?
C2 C2 1.531(4) 3_665 ?
S1B C2B 1.669(5) . ?
C2B N3B 1.291(5) . ?
C2B C2B 1.5349(11) 3_665 ?
N3B H3BA 0.9000 . ?
N3B H3BB 0.8999 . ?

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
C2A N1A C13A 116.8(2) . . ?
N1A C2A C3A 124.6(3) . . ?
N1A C2A H2A 117.7 . . ?
C3A C2A H2A 117.7 . . ?
C4A C3A C2A 118.7(3) . . ?
C4A C3A H3C 120.7 . . ?
C2A C3A H3C 120.7 . . ?
C3A C4A C14A 119.5(2) . . ?
C3A C4A H4A 120.3 . . ?
C14A C4A H4A 120.3 . . ?
C6A C5A C14A 121.5(2) . . ?
C6A C5A H5A 119.3 . . ?
C14A C5A H5A 119.3 . . ?
C5A C6A C12A 121.0(2) . . ?
C5A C6A H6A 119.6 . . ?
C12A C6A H6A 119.3 . . ?
C8A C7A C12A 119.9(2) . . ?
C8A C7A H7A 120.7 . . ?
C12A C7A H7A 119.5 . . ?
C7A C8A C9A 118.5(2) . . ?
C7A C8A H8A 121.1 . . ?
C9A C8A H8A 120.3 . . ?
N10A C9A C8A 123.9(2) . . ?
N10A C9A H9A 117.3 . . ?
C8A C9A H9A 118.8 . . ?
C9A N10A C11A 118.31(18) . . ?
N10A C11A C12A 121.54(19) . . ?
N10A C11A C13A 119.18(18) . . ?
C12A C11A C13A 119.27(18) . . ?
C7A C12A C11A 117.8(2) . . ?
C7A C12A C6A 122.4(2) . . ?
C11A C12A C6A 119.8(2) . . ?
N1A C13A C14A 122.3(2) . . ?
N1A C13A C11A 118.66(17) . . ?
C14A C13A C11A 119.03(19) . . ?
C4A C14A C13A 118.2(2) . . ?
C4A C14A C5A 122.5(2) . . ?
C13A C14A C5A 119.4(2) . . ?
C2 N3 H3A 116.4(17) . . ?
C2 N3 H3B 123.2(17) . . ?
H3A N3 H3B 120(2) . . ?
N3 C2 C2 114.4(2) . 3_665 ?
N3 C2 S1 124.79(19) . . ?
C2 C2 S1 120.8(2) 3_665 . ?
N3B C2B C2B 113.6(7) . 3_665 ?
N3B C2B S1B 124.9(7) . . ?
C2B C2B S1B 121.4(6) 3_665 . ?
C2B N3B H3BA 119.5 . . ?
C2B N3B H3BB 120.5 . . ?
H3BA N3B H3BB 120.0 . . ?

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
N3 H3A S1 0.86(3) 2.42(3) 2.934(3) 119(2) 3_665
N3 H3B N10A 0.87(3) 2.07(3) 2.920(3) 168(2) .
N3 H3B N1A 0.87(3) 2.59(3) 3.011(3) 111(2) .
N3B H3BB S1B 0.90 2.45 2.933(16) 114.3 3_665
N3B H3BA N1A 0.90 2.19 3.073(13) 168.1 3_665

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.314
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.046

#===END


