# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2003 data_global _journal_coden_Cambridge 177 loop_ _publ_author_name 'Wim Dehaen' 'Vasiliy A. Bakulev' 'Mikhail I. Kodess' 'Luc Van Meervelt' 'Evgeniy V. Tarasov' 'Natalya N. Volkova' _publ_contact_author_name 'Prof Wim Dehaen' _publ_contact_author_address ; Chemistry K. U. Leuven Celestijnenlaan 200F Leuven 3001 BELGIUM ; _publ_contact_author_email WIM.DEHAEN@CHEM.KULEUVEN.AC.BE _publ_requested_journal 'Organic & Biomolecular Chemistry' _publ_section_title ; Reaction of 5-halo-1,2,3-thiadiazoles with aliphatic diamines. Synthesis and intramolecular cyclization of bis(1,2,3-triazolyl-1,2,3-thiadiazolyl)sulfides ; data_wim14 _database_code_CSD 214711 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C6 H6 N6 S' _chemical_formula_sum 'C6 H6 N6 S' _chemical_formula_weight 194.23 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 13.4019(2) _cell_length_b 8.13550(10) _cell_length_c 7.84470(10) _cell_angle_alpha 90.00 _cell_angle_beta 101.7440(10) _cell_angle_gamma 90.00 _cell_volume 837.412(19) _cell_formula_units_Z 4 _cell_measurement_temperature 299(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description blocks _exptl_crystal_colour transparent _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.541 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 400 _exptl_absorpt_coefficient_mu 3.129 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.496 _exptl_absorpt_correction_T_max 0.625 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 299(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'crossed Gobel mirrors' _diffrn_measurement_device_type 'SMART 6000' _diffrn_measurement_method 'omega and phi scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 1513 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0127 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 3.37 _diffrn_reflns_theta_max 71.11 _reflns_number_total 1513 _reflns_number_gt 1421 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics PLUTON _computing_publication_material PLATON _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^)+(0.1160P)^2^+0.1032P] 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 SHELXL _refine_ls_extinction_coef 0.033(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1513 _refine_ls_number_parameters 123 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0448 _refine_ls_R_factor_gt 0.0437 _refine_ls_wR_factor_ref 0.1405 _refine_ls_wR_factor_gt 0.1384 _refine_ls_goodness_of_fit_ref 1.001 _refine_ls_restrained_S_all 1.001 _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 S1 S 0.63893(3) 0.85464(7) 0.08435(6) 0.0596(3) Uani 1 1 d . . . N6 N 0.73410(12) 1.10833(19) 0.2991(2) 0.0512(4) Uani 1 1 d . . . N3 N 0.84402(12) 0.8193(2) 0.1691(2) 0.0543(5) Uani 1 1 d . . . C2 C 0.75182(14) 0.7480(2) 0.1526(2) 0.0493(4) Uani 1 1 d . . . C7 C 0.65239(13) 1.0122(2) 0.2397(2) 0.0507(5) Uani 1 1 d . . . N12 N 0.61275(16) 1.2113(3) 0.4064(3) 0.0786(6) Uani 1 1 d . . . N11 N 0.70974(15) 1.2277(2) 0.4027(3) 0.0688(5) Uani 1 1 d . . . N10 N 0.91864(15) 0.7082(2) 0.2162(3) 0.0707(6) Uani 1 1 d . . . C5 C 0.84273(15) 1.0988(3) 0.2903(3) 0.0590(5) Uani 1 1 d . . . H5A H 0.8810(7) 1.0555(8) 0.402(2) 0.071 Uiso 1 1 calc R . . H5B H 0.8678(5) 1.211(2) 0.2764(4) 0.071 Uiso 1 1 calc R . . N9 N 0.87441(18) 0.5641(2) 0.2252(3) 0.0766(6) Uani 1 1 d . . . C4 C 0.86496(15) 0.9936(3) 0.1458(3) 0.0581(5) Uani 1 1 d . . . H4A H 0.8231(8) 1.0318(8) 0.034(2) 0.070 Uiso 1 1 calc R . . H4B H 0.9375(13) 1.0067(4) 0.1393(3) 0.070 Uiso 1 1 calc R . . C8 C 0.77223(19) 0.5851(3) 0.1866(3) 0.0650(6) Uani 1 1 d . . . H8 H 0.7245(15) 0.504(3) 0.1837(3) 0.078 Uiso 1 1 calc R . . C13 C 0.57582(17) 1.0796(3) 0.3097(3) 0.0679(6) Uani 1 1 d . . . H13 H 0.504(2) 1.0379(14) 0.2917(7) 0.082 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 0.0421(4) 0.0683(4) 0.0646(4) -0.0111(2) 0.0019(2) 0.00004(18) N6 0.0476(8) 0.0469(8) 0.0612(9) -0.0018(6) 0.0163(7) 0.0026(6) N3 0.0440(9) 0.0536(9) 0.0668(10) -0.0032(7) 0.0147(7) 0.0053(7) C2 0.0487(9) 0.0499(9) 0.0506(9) -0.0040(7) 0.0133(7) -0.0002(7) C7 0.0423(9) 0.0557(10) 0.0546(10) 0.0027(7) 0.0112(7) 0.0054(7) N12 0.0658(12) 0.0854(14) 0.0894(14) -0.0192(11) 0.0268(10) 0.0140(11) N11 0.0682(11) 0.0607(10) 0.0805(12) -0.0164(9) 0.0224(9) 0.0047(9) N10 0.0525(10) 0.0673(12) 0.0919(13) -0.0054(9) 0.0135(9) 0.0177(9) C5 0.0459(10) 0.0580(11) 0.0756(13) -0.0049(9) 0.0180(9) -0.0071(8) N9 0.0795(13) 0.0610(11) 0.0906(14) 0.0049(9) 0.0205(11) 0.0201(10) C4 0.0481(10) 0.0605(11) 0.0693(12) 0.0030(9) 0.0207(9) -0.0027(8) C8 0.0761(14) 0.0495(10) 0.0726(13) -0.0031(9) 0.0225(11) -0.0016(10) C13 0.0478(10) 0.0829(15) 0.0763(14) -0.0037(11) 0.0202(9) 0.0113(10) _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 1.7318(19) . ? S1 C7 1.752(2) . ? N6 C7 1.349(3) . ? N6 N11 1.349(2) . ? N6 C5 1.473(2) . ? N3 N10 1.343(2) . ? N3 C2 1.348(2) . ? N3 C4 1.464(3) . ? C2 C8 1.368(3) . ? C7 C13 1.373(3) . ? N12 N11 1.313(3) . ? N12 C13 1.347(4) . ? N10 N9 1.322(3) . ? C5 C4 1.498(3) . ? C5 H5A 0.9830 . ? C5 H5B 0.9830 . ? N9 C8 1.352(3) . ? C4 H4A 0.9899 . ? C4 H4B 0.9899 . ? C8 H8 0.9179 . ? C13 H13 0.9998 . ? 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 C2 S1 C7 101.04(8) . . ? C7 N6 N11 110.29(16) . . ? C7 N6 C5 133.91(17) . . ? N11 N6 C5 115.38(17) . . ? N10 N3 C2 110.68(17) . . ? N10 N3 C4 122.38(16) . . ? C2 N3 C4 126.91(17) . . ? N3 C2 C8 104.80(18) . . ? N3 C2 S1 122.69(15) . . ? C8 C2 S1 132.30(17) . . ? N6 C7 C13 104.49(19) . . ? N6 C7 S1 128.73(14) . . ? C13 C7 S1 126.23(17) . . ? N11 N12 C13 108.67(18) . . ? N12 N11 N6 107.59(18) . . ? N9 N10 N3 107.15(18) . . ? N6 C5 C4 114.58(17) . . ? N6 C5 H5A 108.6 . . ? C4 C5 H5A 108.6 . . ? N6 C5 H5B 108.6 . . ? C4 C5 H5B 108.6 . . ? H5A C5 H5B 107.6 . . ? N10 N9 C8 108.73(18) . . ? N3 C4 C5 112.72(17) . . ? N3 C4 H4A 109.0 . . ? C5 C4 H4A 109.0 . . ? N3 C4 H4B 109.0 . . ? C5 C4 H4B 109.0 . . ? H4A C4 H4B 107.8 . . ? N9 C8 C2 108.6(2) . . ? N9 C8 H8 125.7 . . ? C2 C8 H8 125.7 . . ? N12 C13 C7 108.9(2) . . ? N12 C13 H13 125.5 . . ? C7 C13 H13 125.5 . . ? _diffrn_measured_fraction_theta_max 0.935 _diffrn_reflns_theta_full 71.11 _diffrn_measured_fraction_theta_full 0.935 _refine_diff_density_max 0.327 _refine_diff_density_min -0.219 _refine_diff_density_rms 0.051