# 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 \k geometry' _diffrn_measurement_method '\w 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>2\s(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 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^)+(0.0677P)^2^+0.0512P] where P=(Fo^2^+2Fc^2^)/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+0.001xFc^2^\l^3^/sin(2\q)]^-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 \k geometry' _diffrn_measurement_method '\w 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>2\s(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 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^)+(0.0705P)^2^] where P=(Fo^2^+2Fc^2^)/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 \k geometry' _diffrn_measurement_method '\w 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>2\s(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 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^)+(0.0585P)^2^P] 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 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 \k geometry' _diffrn_measurement_method '\w 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>2\s(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 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^)+(0.0570P)^2^+1.4584P] 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 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 \k geometry' _diffrn_measurement_method '\w 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>2\s(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 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^)+(0.0873P)^2^+0.2318P] 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 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 \k geometry' _diffrn_measurement_method '\w 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>2\s(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 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^)+(0.0505P)^2^] where P=(Fo^2^+2Fc^2^)/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 \k geometry' _diffrn_measurement_method '\w 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 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^)+(0.0850P)^2^+0.1893P] where P=(Fo^2^+2Fc^2^)/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+0.001xFc^2^\l^3^/sin(2\q)]^-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