# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_coden_Cambridge 1350 loop_ _publ_author_name 'Lenthall, Joseph' 'Foster, Jonathan' 'Anderson, Kirsty' 'Probert, Michael' 'Howard, Judith' 'Steed, Jonathan' _publ_contact_author_name 'Steed, Jonathan' _publ_contact_author_email jon.steed@durham.ac.uk _publ_section_title ; Hydrogen bonding interactions with the thiocarbonyl p-system ; #TrackingRef '- 1.cif' _publ_requested_journal ? # Attachment '- 1.cif' data_G6A2 _database_code_depnum_ccdc_archive 'CCDC 795070' _audit_creation_method SHELXL-97 _chemical_formula_moiety 'C8 H11 N3 S' _chemical_formula_sum 'C8 H11 N3 S' _chemical_formula_weight 181.26 _chemical_melting_point ? _chemical_name_common ? _chemical_name_systematic ? 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' _space_group_IT_number 14 _space_group_crystal_system monoclinic _space_group_name_H-M_alt 'P 1 21/n 1' _space_group_name_Hall '-P 2yn' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x+1/2, y+1/2, -z+1/2' 3 '-x, -y, -z' 4 'x-1/2, -y-1/2, z-1/2' _cell_angle_alpha 90.00 _cell_angle_beta 105.323(4) _cell_angle_gamma 90.00 _cell_formula_units_Z 8 _cell_length_a 14.7266(6) _cell_length_b 7.6637(3) _cell_length_c 16.2667(7) _cell_measurement_reflns_used 4870 _cell_measurement_temperature 120(2) _cell_measurement_theta_max 28.9702 _cell_measurement_theta_min 2.5913 _cell_volume 1770.61(12) _exptl_absorpt_coefficient_mu 0.312 _exptl_absorpt_correction_T_max 1.0 _exptl_absorpt_correction_T_min 0.68342 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.23 (release 20-04-2010 CrysAlis171 .NET) (compiled Apr 20 2010,18:09:47) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_F_000 768 _exptl_crystal_colour ? _exptl_crystal_colour_lustre clear _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.360 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_recrystallization_method 'Recrystalised from methanol' _exptl_crystal_size_max 0.7434 _exptl_crystal_size_mid 0.3342 _exptl_crystal_size_min 0.2347 _exptl_special_details ? _diffrn_ambient_temperature 120(2) _diffrn_detector_area_resol_mean 16.1511 _diffrn_measured_fraction_theta_full 0.874 _diffrn_measured_fraction_theta_max 0.874 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -95.00 -61.00 1.0000 16.4500 omega____ theta____ kappa____ phi______ frames - -18.0928 179.0000 -60.0000 34 #__ type_ start__ end____ width___ exp.time_ 2 omega -86.00 36.00 1.0000 16.4500 omega____ theta____ kappa____ phi______ frames - -18.0928 0.0000 -30.0000 122 #__ type_ start__ end____ width___ exp.time_ 3 omega -80.00 1.00 1.0000 16.4500 omega____ theta____ kappa____ phi______ frames - -18.0928 -38.0000 90.0000 81 ; _diffrn_measurement_device_type 'Xcalibur, Sapphire3, Gemini ultra' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 0.0153938 _diffrn_orient_matrix_UB_12 0.029797 _diffrn_orient_matrix_UB_13 0.0426972 _diffrn_orient_matrix_UB_21 0.0444419 _diffrn_orient_matrix_UB_22 0.0219892 _diffrn_orient_matrix_UB_23 -0.0064169 _diffrn_orient_matrix_UB_31 -0.0168424 _diffrn_orient_matrix_UB_32 0.0848275 _diffrn_orient_matrix_UB_33 -0.0133567 _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_reflns_av_R_equivalents 0.0635 _diffrn_reflns_av_sigmaI/netI 0.0718 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_number 8107 _diffrn_reflns_theta_full 29.03 _diffrn_reflns_theta_max 29.03 _diffrn_reflns_theta_min 2.60 _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 3508 _reflns_number_total 4136 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.23 (release 20-04-2010 CrysAlis171 .NET) (compiled Apr 20 2010,18:09:47) ; _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.23 (release 20-04-2010 CrysAlis171 .NET) (compiled Apr 20 2010,18:09:47) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.23 (release 20-04-2010 CrysAlis171 .NET) (compiled Apr 20 2010,18:09:47) ; _computing_molecular_graphics ; OLEX2: a complete structure solution, refinement and analysis program. Dolomanov et al., J. Appl. Cryst. (2009). 42, 339-341 ; _computing_publication_material ; OLEX2: a complete structure solution, refinement and analysis program. Dolomanov et al., J. Appl. Cryst. (2009). 42, 339-341 ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'A short history of SHELX (Sheldrick, 2007)' _refine_diff_density_max 0.642 _refine_diff_density_min -0.478 _refine_diff_density_rms 0.115 _refine_ls_R_factor_all 0.0620 _refine_ls_R_factor_gt 0.0531 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.064 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 235 _refine_ls_number_reflns 4136 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.064 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_wR_factor_gt 0.1373 _refine_ls_wR_factor_ref 0.1486 _refine_ls_weighting_details ; calc w=1/[\s^2^(Fo^2^)+(0.0843P)^2^+0.1851P] where P=(Fo^2^+2Fc^2^)/3 ; _refine_ls_weighting_scheme calc _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. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 0.22371(4) 0.09019(6) 0.10271(3) 0.01509(16) Uani 1 1 d . . . S2 S 0.47488(3) 1.03985(6) -0.13913(3) 0.01453(16) Uani 1 1 d . . . N2 N 0.37999(11) 0.2390(2) 0.19349(11) 0.0144(4) Uani 1 1 d . . . H2 H 0.4034 0.1910 0.1559 0.017 Uiso 1 1 calc R . . N1 N 0.50022(13) 0.4850(2) 0.15408(12) 0.0166(4) Uani 1 1 d . . . N5 N 0.37830(12) 0.7837(2) -0.09302(11) 0.0140(4) Uani 1 1 d . . . H5A H 0.4154 0.7185 -0.1124 0.017 Uiso 1 1 calc R . . N6 N 0.34387(12) 1.0596(2) -0.05437(12) 0.0144(4) Uani 1 1 d . . . H6 H 0.3014 1.0126 -0.0341 0.017 Uiso 1 1 calc R . . N4 N 0.23711(14) 0.6027(3) -0.21050(12) 0.0212(4) Uani 1 1 d . . . C15 C 0.39393(14) 0.9569(3) -0.09136(12) 0.0122(4) Uani 1 1 d . . . C1 C 0.50484(14) 0.4506(2) 0.24009(13) 0.0135(4) Uani 1 1 d . . . C7 C 0.28568(14) 0.2225(2) 0.18088(12) 0.0122(4) Uani 1 1 d . . . C14 C 0.30471(14) 0.6983(2) -0.06507(13) 0.0134(4) Uani 1 1 d . . . C13 C 0.30506(14) 0.6968(2) 0.02011(13) 0.0150(4) Uani 1 1 d . . . H13 H 0.3533 0.7526 0.0600 0.018 Uiso 1 1 calc R . . C9 C 0.23356(14) 0.6132(3) -0.12636(13) 0.0148(4) Uani 1 1 d . . . C16 C 0.35703(15) 1.2478(3) -0.04634(14) 0.0178(4) Uani 1 1 d . . . H16B H 0.3411 1.2999 -0.1020 0.027 Uiso 1 1 calc R . . H16C H 0.4216 1.2730 -0.0180 0.027 Uiso 1 1 calc R . . H16A H 0.3171 1.2947 -0.0137 0.027 Uiso 1 1 calc R . . C10 C 0.16241(15) 0.5294(3) -0.09918(15) 0.0196(5) Uani 1 1 d . . . H10 H 0.1143 0.4725 -0.1387 0.024 Uiso 1 1 calc R . . C6 C 0.44495(13) 0.3261(2) 0.26129(13) 0.0127(4) Uani 1 1 d . . . C2 C 0.57146(15) 0.5324(3) 0.30582(15) 0.0190(5) Uani 1 1 d . . . H2A H 0.6128 0.6128 0.2927 0.023 Uiso 1 1 calc R . . C5 C 0.45257(15) 0.2875(3) 0.34613(14) 0.0167(4) Uani 1 1 d . . . H5 H 0.4135 0.2031 0.3598 0.020 Uiso 1 1 calc R . . C8 C 0.14355(14) 0.3058(3) 0.22337(15) 0.0203(5) Uani 1 1 d . . . H8A H 0.1102 0.3497 0.1684 0.030 Uiso 1 1 calc R . . H8C H 0.1291 0.3762 0.2670 0.030 Uiso 1 1 calc R . . H8B H 0.1249 0.1874 0.2292 0.030 Uiso 1 1 calc R . . C4 C 0.51740(15) 0.3726(3) 0.41064(14) 0.0194(4) Uani 1 1 d . . . H4 H 0.5212 0.3478 0.4674 0.023 Uiso 1 1 calc R . . C11 C 0.16281(16) 0.5301(3) -0.01412(16) 0.0210(5) Uani 1 1 d . . . H11 H 0.1146 0.4745 0.0028 0.025 Uiso 1 1 calc R . . C3 C 0.57694(15) 0.4959(3) 0.38970(14) 0.0208(5) Uani 1 1 d . . . H3 H 0.6207 0.5540 0.4327 0.025 Uiso 1 1 calc R . . C12 C 0.23410(16) 0.6127(3) 0.04650(15) 0.0195(5) Uani 1 1 d . . . H12 H 0.2343 0.6117 0.1037 0.023 Uiso 1 1 calc R . . N3 N 0.24462(12) 0.3121(2) 0.23174(11) 0.0158(4) Uani 1 1 d . . . H3A H 0.2793 0.3762 0.2711 0.019 Uiso 1 1 calc R . . H4B H 0.2706(18) 0.680(3) -0.2271(17) 0.018(6) Uiso 1 1 d . . . H1A H 0.4393(19) 0.473(3) 0.1173(17) 0.020(6) Uiso 1 1 d . . . H4A H 0.179(2) 0.588(4) -0.247(2) 0.035(8) Uiso 1 1 d . . . H1B H 0.520(2) 0.583(4) 0.1493(19) 0.029(8) 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 S1 0.0157(3) 0.0169(3) 0.0122(3) -0.00287(18) 0.0030(2) -0.00508(19) S2 0.0127(3) 0.0160(3) 0.0166(3) 0.00054(19) 0.0069(2) -0.00006(18) N2 0.0126(8) 0.0165(8) 0.0154(9) -0.0053(7) 0.0057(7) -0.0033(7) N1 0.0195(10) 0.0154(9) 0.0157(9) 0.0003(7) 0.0062(8) -0.0035(7) N5 0.0133(8) 0.0119(8) 0.0186(9) -0.0001(7) 0.0076(7) 0.0026(6) N6 0.0154(8) 0.0129(8) 0.0173(9) 0.0021(7) 0.0084(7) 0.0011(7) N4 0.0194(10) 0.0301(11) 0.0128(9) -0.0024(8) 0.0019(8) -0.0023(8) C15 0.0107(9) 0.0151(10) 0.0096(9) 0.0004(7) 0.0006(7) 0.0002(7) C1 0.0119(9) 0.0139(9) 0.0156(10) -0.0010(8) 0.0052(8) 0.0021(7) C7 0.0146(9) 0.0101(9) 0.0114(9) 0.0021(7) 0.0027(7) -0.0010(7) C14 0.0134(9) 0.0099(9) 0.0172(10) 0.0013(7) 0.0047(8) 0.0029(7) C13 0.0176(10) 0.0119(9) 0.0150(10) 0.0003(7) 0.0034(8) 0.0010(8) C9 0.0144(10) 0.0132(9) 0.0160(10) 0.0007(8) 0.0024(8) 0.0029(7) C16 0.0222(11) 0.0134(9) 0.0202(11) -0.0004(8) 0.0097(9) 0.0008(8) C10 0.0164(10) 0.0168(10) 0.0243(12) -0.0021(9) 0.0030(9) -0.0027(8) C6 0.0097(9) 0.0118(9) 0.0166(10) -0.0024(7) 0.0036(7) 0.0017(7) C2 0.0150(10) 0.0168(10) 0.0255(12) -0.0022(8) 0.0056(9) -0.0020(8) C5 0.0156(10) 0.0168(10) 0.0198(11) 0.0018(8) 0.0086(8) 0.0012(8) C8 0.0123(10) 0.0225(11) 0.0267(12) -0.0036(9) 0.0064(8) -0.0007(8) C4 0.0200(11) 0.0234(11) 0.0139(10) 0.0000(9) 0.0028(8) 0.0050(9) C11 0.0184(11) 0.0167(10) 0.0314(13) 0.0005(9) 0.0127(9) -0.0019(8) C3 0.0155(10) 0.0242(11) 0.0192(11) -0.0074(9) -0.0015(8) 0.0003(9) C12 0.0260(12) 0.0155(10) 0.0205(11) 0.0027(8) 0.0123(9) 0.0025(9) N3 0.0137(8) 0.0178(8) 0.0170(9) -0.0051(7) 0.0060(7) -0.0011(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 S1 C7 1.693(2) . ? S2 C15 1.708(2) . ? N2 C7 1.355(2) . ? N2 C6 1.421(2) . ? N1 C1 1.408(3) . ? N5 C15 1.347(2) . ? N5 C14 1.439(2) . ? N6 C15 1.326(2) . ? N6 C16 1.457(3) . ? N4 C9 1.386(3) . ? C1 C6 1.403(3) . ? C1 C2 1.394(3) . ? C7 N3 1.336(2) . ? C14 C13 1.384(3) . ? C14 C9 1.402(3) . ? C13 C12 1.389(3) . ? C9 C10 1.397(3) . ? C10 C11 1.382(3) . ? C6 C5 1.387(3) . ? C2 C3 1.374(3) . ? C5 C4 1.382(3) . ? C8 N3 1.459(3) . ? C4 C3 1.391(3) . ? C11 C12 1.389(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 C7 S1 119.83(14) . . ? N5 C15 S2 119.59(14) . . ? N6 C15 S2 121.59(15) . . ? N6 C15 N5 118.79(17) . . ? N4 C9 C14 120.89(18) . . ? N4 C9 C10 120.9(2) . . ? C15 N5 C14 125.52(16) . . ? C15 N6 C16 123.48(17) . . ? C1 C6 N2 117.81(18) . . ? C7 N2 C6 127.90(16) . . ? C7 N3 C8 122.88(18) . . ? C14 C13 C12 120.6(2) . . ? C13 C14 N5 121.09(18) . . ? C13 C14 C9 120.82(18) . . ? C9 C14 N5 118.07(18) . . ? C10 C9 C14 118.10(19) . . ? C10 C11 C12 121.02(19) . . ? C6 C1 N1 120.24(19) . . ? C2 C1 N1 121.14(18) . . ? C2 C1 C6 118.55(19) . . ? C2 C3 C4 120.4(2) . . ? C5 C6 N2 122.20(17) . . ? C5 C6 C1 119.95(19) . . ? C5 C4 C3 119.2(2) . . ? C4 C5 C6 120.86(19) . . ? C11 C10 C9 120.7(2) . . ? C11 C12 C13 118.8(2) . . ? C3 C2 C1 120.98(19) . . ? N3 C7 S1 122.03(15) . . ? N3 C7 N2 118.14(18) . . ? # Attachment '- 2.CIF' data_06srv197 _database_code_depnum_ccdc_archive 'CCDC 795071' #TrackingRef '- 2.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H17 N3 S' _chemical_formula_sum 'C11 H17 N3 S' _chemical_formula_weight 223.34 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 P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 10.6285(4) _cell_length_b 9.7517(4) _cell_length_c 12.8232(5) _cell_angle_alpha 90.00 _cell_angle_beta 109.7120(10) _cell_angle_gamma 90.00 _cell_volume 1251.19(9) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.39 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.186 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 480 _exptl_absorpt_coefficient_mu 0.233 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.948 _exptl_absorpt_correction_T_max 0.959 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(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 'SMART 1k' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11735 _diffrn_reflns_av_R_equivalents 0.0598 _diffrn_reflns_av_sigmaI/netI 0.0428 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.16 _diffrn_reflns_theta_max 30.42 _reflns_number_total 3477 _reflns_number_gt 2825 _reflns_threshold_expression >2sigma(I) _computing_data_collection SMART _computing_cell_refinement SMART _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics XP _computing_publication_material XP _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^)+(0.0427P)^2^+0.3752P] 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 3477 _refine_ls_number_parameters 144 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0494 _refine_ls_R_factor_gt 0.0373 _refine_ls_wR_factor_ref 0.0982 _refine_ls_wR_factor_gt 0.0922 _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_restrained_S_all 1.042 _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 0.34849(3) 0.90144(3) 0.06016(3) 0.02076(10) Uani 1 1 d . . . N1 N 0.60786(10) 0.85756(11) 0.11123(9) 0.0197(2) Uani 1 1 d . . . H1N H 0.6063 0.9365 0.0776 0.024 Uiso 1 1 calc R . . N2 N 0.50344(11) 0.70530(11) 0.19046(10) 0.0223(2) Uani 1 1 d . . . H2N H 0.5828 0.6663 0.2129 0.027 Uiso 1 1 calc R . . N3 N 0.77433(15) 0.84851(16) 0.33966(11) 0.0355(3) Uani 1 1 d . . . C1 C 0.73142(12) 0.78342(12) 0.14731(10) 0.0182(2) Uani 1 1 d . . . C2 C 0.77600(13) 0.72130(14) 0.06879(11) 0.0233(3) Uani 1 1 d . . . H2 H 0.7249 0.7300 -0.0076 0.028 Uiso 1 1 calc R . . C3 C 0.89406(14) 0.64670(15) 0.10018(12) 0.0276(3) Uani 1 1 d . . . H3 H 0.9256 0.6070 0.0460 0.033 Uiso 1 1 calc R . . C4 C 0.96544(13) 0.63110(14) 0.21242(12) 0.0251(3) Uani 1 1 d . . . H4 H 1.0442 0.5766 0.2351 0.030 Uiso 1 1 calc R . . C5 C 0.92326(13) 0.69369(14) 0.29106(11) 0.0246(3) Uani 1 1 d . . . H5 H 0.9734 0.6814 0.3673 0.030 Uiso 1 1 calc R . . C6 C 0.80767(13) 0.77538(13) 0.26091(11) 0.0214(3) Uani 1 1 d . . . C7 C 0.49304(12) 0.81499(12) 0.12512(10) 0.0176(2) Uani 1 1 d . . . C8 C 0.40322(13) 0.63870(13) 0.23120(11) 0.0208(3) Uani 1 1 d . . . C9 C 0.29245(16) 0.57360(16) 0.13491(13) 0.0328(3) Uani 1 1 d . . . H9A H 0.2436 0.6455 0.0838 0.049 Uiso 1 1 calc R . . H9B H 0.2308 0.5240 0.1635 0.049 Uiso 1 1 calc R . . H9C H 0.3319 0.5096 0.0957 0.049 Uiso 1 1 calc R . . C10 C 0.34572(16) 0.74034(15) 0.29325(12) 0.0303(3) Uani 1 1 d . . . H10A H 0.4185 0.7806 0.3546 0.045 Uiso 1 1 calc R . . H10B H 0.2835 0.6927 0.3225 0.045 Uiso 1 1 calc R . . H10C H 0.2982 0.8131 0.2426 0.045 Uiso 1 1 calc R . . C11 C 0.48098(16) 0.52821(16) 0.31223(14) 0.0353(4) Uani 1 1 d . . . H11A H 0.5518 0.5714 0.3734 0.053 Uiso 1 1 calc R . . H11B H 0.5209 0.4639 0.2736 0.053 Uiso 1 1 calc R . . H11C H 0.4201 0.4786 0.3416 0.053 Uiso 1 1 calc R . . H3N H 0.801(2) 0.814(2) 0.4081(19) 0.051(6) Uiso 1 1 d . . . H4N H 0.704(2) 0.8971(19) 0.3193(15) 0.035(5) 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 S1 0.01679(16) 0.02006(15) 0.02312(16) 0.00464(11) 0.00368(12) 0.00038(11) N1 0.0181(5) 0.0180(5) 0.0220(5) 0.0063(4) 0.0054(4) -0.0002(4) N2 0.0187(5) 0.0186(5) 0.0320(6) 0.0082(4) 0.0119(5) 0.0029(4) N3 0.0365(8) 0.0459(8) 0.0208(6) -0.0021(6) 0.0052(5) 0.0161(6) C1 0.0159(5) 0.0182(5) 0.0199(6) 0.0037(4) 0.0052(5) -0.0011(4) C2 0.0229(6) 0.0274(6) 0.0197(6) 0.0022(5) 0.0074(5) -0.0014(5) C3 0.0275(7) 0.0314(7) 0.0277(7) 0.0005(6) 0.0145(6) 0.0029(6) C4 0.0189(6) 0.0252(6) 0.0323(7) 0.0068(5) 0.0099(5) 0.0025(5) C5 0.0207(6) 0.0280(6) 0.0224(6) 0.0058(5) 0.0036(5) 0.0005(5) C6 0.0218(6) 0.0224(6) 0.0194(6) 0.0017(5) 0.0061(5) -0.0008(5) C7 0.0189(6) 0.0152(5) 0.0180(5) -0.0003(4) 0.0052(5) -0.0011(4) C8 0.0223(6) 0.0173(5) 0.0267(6) 0.0025(5) 0.0136(5) 0.0000(5) C9 0.0399(8) 0.0278(7) 0.0338(8) -0.0056(6) 0.0165(7) -0.0151(6) C10 0.0408(8) 0.0275(7) 0.0289(7) -0.0008(5) 0.0199(7) 0.0046(6) C11 0.0344(8) 0.0283(7) 0.0486(9) 0.0189(7) 0.0211(7) 0.0065(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C7 1.7034(13) . ? N1 C7 1.3564(16) . ? N1 C1 1.4323(16) . ? N1 H1N 0.8800 . ? N2 C7 1.3402(15) . ? N2 C8 1.4848(16) . ? N2 H2N 0.8800 . ? N3 C6 1.3767(18) . ? N3 H3N 0.89(2) . ? N3 H4N 0.85(2) . ? C1 C2 1.3882(18) . ? C1 C6 1.4101(17) . ? C2 C3 1.3874(19) . ? C2 H2 0.9500 . ? C3 C4 1.391(2) . ? C3 H3 0.9500 . ? C4 C5 1.377(2) . ? C4 H4 0.9500 . ? C5 C6 1.4047(18) . ? C5 H5 0.9500 . ? C8 C10 1.5222(18) . ? C8 C9 1.527(2) . ? C8 C11 1.5311(19) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? 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 C7 N1 C1 124.79(10) . . ? C7 N1 H1N 117.6 . . ? C1 N1 H1N 117.6 . . ? C7 N2 C8 130.65(11) . . ? C7 N2 H2N 114.7 . . ? C8 N2 H2N 114.7 . . ? C6 N3 H3N 116.8(13) . . ? C6 N3 H4N 118.9(12) . . ? H3N N3 H4N 117.9(18) . . ? C2 C1 C6 120.48(12) . . ? C2 C1 N1 119.08(11) . . ? C6 C1 N1 120.44(11) . . ? C3 C2 C1 120.99(12) . . ? C3 C2 H2 119.5 . . ? C1 C2 H2 119.5 . . ? C2 C3 C4 118.81(13) . . ? C2 C3 H3 120.6 . . ? C4 C3 H3 120.6 . . ? C5 C4 C3 120.72(13) . . ? C5 C4 H4 119.6 . . ? C3 C4 H4 119.6 . . ? C4 C5 C6 121.36(12) . . ? C4 C5 H5 119.3 . . ? C6 C5 H5 119.3 . . ? N3 C6 C5 120.63(12) . . ? N3 C6 C1 121.90(12) . . ? C5 C6 C1 117.41(12) . . ? N2 C7 N1 115.99(11) . . ? N2 C7 S1 124.84(10) . . ? N1 C7 S1 119.17(9) . . ? N2 C8 C10 111.18(11) . . ? N2 C8 C9 110.26(11) . . ? C10 C8 C9 110.93(12) . . ? N2 C8 C11 105.04(11) . . ? C10 C8 C11 108.87(12) . . ? C9 C8 C11 110.40(12) . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C8 C10 H10A 109.5 . . ? C8 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C8 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C8 C11 H11A 109.5 . . ? C8 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C8 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.917 _diffrn_reflns_theta_full 30.42 _diffrn_measured_fraction_theta_full 0.917 _refine_diff_density_max 0.331 _refine_diff_density_min -0.319 _refine_diff_density_rms 0.050 # Attachment '- 3.cif' data_jws1 _database_code_depnum_ccdc_archive 'CCDC 795072' #TrackingRef '- 3.cif' _audit_creation_date 2010-09-28 _audit_creation_method ; Olex2 1.1-beta (compiled 2010.09.10 svn.r1414, GUI svn.r3225) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C6 H14 N4 S2' _chemical_formula_sum 'C6 H14 N4 S2' _chemical_formula_weight 206.33 _chemical_melting_point ? 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' _space_group_crystal_system tetragonal _space_group_IT_number 86 _space_group_name_H-M_alt 'P 42/n' _space_group_name_Hall '-P 4bc' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-y, x+1/2, z+1/2' 3 '-x+1/2, -y+1/2, z' 4 'y+1/2, -x, z+1/2' 5 '-x, -y, -z' 6 'y, -x-1/2, -z-1/2' 7 'x-1/2, y-1/2, -z' 8 '-y-1/2, x, -z-1/2' _symmetry_cell_setting Tetragonal _symmetry_space_group_name_H-M P4(2)/n _cell_length_a 9.5098(5) _cell_length_b 9.5098(5) _cell_length_c 10.8333(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 979.72(10) _cell_formula_units_Z 4 _cell_measurement_reflns_used 1455 _cell_measurement_temperature 200 _cell_measurement_theta_max 26.83 _cell_measurement_theta_min 2.85 _exptl_absorpt_coefficient_mu 0.498 _exptl_absorpt_correction_T_max ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_type none _exptl_absorpt_process_details ? _exptl_crystal_colour colourless _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.399 _exptl_crystal_density_meas . _exptl_crystal_density_method ? _exptl_crystal_description block _exptl_crystal_F_000 440 _exptl_crystal_size_max 0.09 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.05 _exptl_special_details ; The data collection nominally covered a full sphere of reciprocal space by a combination of 4 sets of \w scans each set at different \f and/or 2\q angles and each scan (60.00 s exposure) covering -0.300\ degrees in \w. The crystal to detector distance was 4.85 cm. ; _diffrn_ambient_temperature 200 _diffrn_detector 'CCD area detector' _diffrn_detector_area_resol_mean 5.6 _diffrn_detector_type 'Bruker SMART CCD 6000 area detector' _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device 'three-circle diffractometer' _diffrn_measurement_device_type 'Bruker SMART CCD 6000 area detector' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 0.038066 _diffrn_orient_matrix_UB_12 -0.067548 _diffrn_orient_matrix_UB_13 0.062351 _diffrn_orient_matrix_UB_21 -0.062970 _diffrn_orient_matrix_UB_22 0.041643 _diffrn_orient_matrix_UB_23 0.064283 _diffrn_orient_matrix_UB_31 -0.075092 _diffrn_orient_matrix_UB_32 -0.069024 _diffrn_orient_matrix_UB_33 -0.022240 _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_xray_symbol K-L~3~ _diffrn_reflns_av_R_equivalents 0.0608 _diffrn_reflns_av_sigmaI/netI 0.0461 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 6601 _diffrn_reflns_theta_full 26.37 _diffrn_reflns_theta_max 26.37 _diffrn_reflns_theta_min 2.85 _diffrn_source 'sealed X-ray tube' _diffrn_source_current 35.0 _diffrn_source_power 1.75 _diffrn_source_target Mo _diffrn_source_voltage 50.0 _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 716 _reflns_number_total 1002 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement 'SAINT v6.45A (Bruker, 2003)' _computing_data_collection 'SMART v5.625 (Bruker, 2001)' _computing_data_reduction 'SAINT v6.45A (Bruker, 2003)' _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'A short history of SHELX (Sheldrick, 2007)/Bruker' _refine_diff_density_max 0.209 _refine_diff_density_min -0.220 _refine_diff_density_rms 0.047 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.921 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 56 _refine_ls_number_reflns 1002 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0514 _refine_ls_R_factor_gt 0.0296 _refine_ls_restrained_S_all 0.921 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0360P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0625 _refine_ls_wR_factor_ref 0.0685 _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. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 0.10525(5) 0.47966(5) 0.17890(4) 0.02688(16) Uani 1 1 d . . . N2 N 0.09555(15) 0.74683(15) 0.25753(13) 0.0213(3) Uani 1 1 d . . . H2 H 0.0679 0.8344 0.2479 0.026 Uiso 1 1 calc R . . C2 C 0.05801(18) 0.65297(18) 0.17119(16) 0.0200(4) Uani 1 1 d . . . N1 N -0.02338(15) 0.69749(15) 0.07867(14) 0.0231(4) Uani 1 1 d . . . H1 H -0.0431 0.6367 0.0199 0.028 Uiso 1 1 calc R . . C1 C -0.0820(2) 0.83771(19) 0.06699(18) 0.0284(5) Uani 1 1 d . . . H1A H -0.1246 0.8484 -0.0148 0.043 Uiso 1 1 calc R . . H1C H -0.0070 0.9075 0.0773 0.043 Uiso 1 1 calc R . . H1B H -0.1538 0.8520 0.1306 0.043 Uiso 1 1 calc R . . C3 C 0.17901(19) 0.71320(19) 0.36599(16) 0.0228(4) Uani 1 1 d . . . H3A H 0.1940 0.6103 0.3695 0.027 Uiso 1 1 calc R . . H3B H 0.1262 0.7410 0.4409 0.027 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 0.0336(3) 0.0201(3) 0.0270(3) -0.0036(2) -0.0051(2) 0.0053(2) N2 0.0237(8) 0.0179(8) 0.0223(8) 0.0009(7) -0.0016(7) -0.0011(6) C2 0.0156(8) 0.0222(9) 0.0221(10) -0.0008(8) 0.0059(8) -0.0022(7) N1 0.0274(8) 0.0202(8) 0.0218(9) -0.0042(7) -0.0050(7) 0.0036(6) C1 0.0310(11) 0.0237(10) 0.0305(11) -0.0002(9) -0.0030(9) 0.0068(8) C3 0.0268(10) 0.0249(10) 0.0166(9) 0.0020(8) 0.0018(8) -0.0043(8) _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 1.7103(18) . ? N2 C2 1.341(2) . ? N2 C3 1.454(2) . ? C2 N1 1.335(2) . ? N1 C1 1.451(2) . ? C3 C3 1.521(3) 3_565 ? 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 N2 C2 S1 122.50(14) . . ? N2 C3 C3 112.55(12) . 3_565 ? C2 N2 C3 124.24(16) . . ? C2 N1 C1 125.41(15) . . ? N1 C2 S1 119.63(13) . . ? N1 C2 N2 117.82(16) . . ? # Attachment '- 4.CIF' data_x:\groupc~1\joelen~1\05srv2~1\05srv235 _database_code_depnum_ccdc_archive 'CCDC 795073' #TrackingRef '- 4.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C10 H14 N4 S2' _chemical_formula_sum 'C10 H14 N4 S2' _chemical_formula_weight 254.37 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' 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 18.0632(8) _cell_length_b 7.5649(3) _cell_length_c 19.4089(8) _cell_angle_alpha 90.00 _cell_angle_beta 116.0840(10) _cell_angle_gamma 90.00 _cell_volume 2382.03(17) _cell_formula_units_Z 8 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 8596 _cell_measurement_theta_min 2.33 _cell_measurement_theta_max 30.29 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.419 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1072 _exptl_absorpt_coefficient_mu 0.425 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(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 'Bruker SMART-1K CCD Diffractometer' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 13725 _diffrn_reflns_av_R_equivalents 0.0269 _diffrn_reflns_av_sigmaI/netI 0.0232 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 2.34 _diffrn_reflns_theta_max 30.34 _reflns_number_total 3395 _reflns_number_gt 2966 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART V5.049 (Bruker, 2002)' _computing_cell_refinement 'SMART v5.630 (Bruker 2002)' _computing_data_reduction 'SAINT v6.45A (Bruker, 2002)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0377P)^2^+1.9296P] 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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3395 _refine_ls_number_parameters 201 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0366 _refine_ls_R_factor_gt 0.0296 _refine_ls_wR_factor_ref 0.0769 _refine_ls_wR_factor_gt 0.0735 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_restrained_S_all 1.054 _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 0.004476(18) 0.07598(4) 0.094054(17) 0.01668(8) Uani 1 1 d . . . S2 S 0.307401(19) 0.04595(4) -0.072422(18) 0.01813(8) Uani 1 1 d . . . N1 N 0.09268(6) -0.21887(14) 0.10977(6) 0.0174(2) Uani 1 1 d . . . N2 N 0.15665(6) 0.04408(14) 0.11139(6) 0.01533(19) Uani 1 1 d . . . N3 N 0.20869(6) 0.00959(15) -0.00036(6) 0.0172(2) Uani 1 1 d . . . N4 N 0.14624(7) 0.09419(15) -0.12388(6) 0.0192(2) Uani 1 1 d . . . C1 C 0.23564(7) -0.03248(15) 0.13040(7) 0.0145(2) Uani 1 1 d . . . C2 C 0.26454(7) -0.04307(15) 0.07377(7) 0.0145(2) Uani 1 1 d . . . C3 C 0.34382(8) -0.10849(17) 0.09477(7) 0.0187(2) Uani 1 1 d . . . C4 C 0.39219(8) -0.16199(18) 0.16998(7) 0.0203(2) Uani 1 1 d . . . C5 C 0.36336(8) -0.15311(18) 0.22544(7) 0.0205(2) Uani 1 1 d . . . C6 C 0.28486(8) -0.08723(17) 0.20513(7) 0.0185(2) Uani 1 1 d . . . C7 C 0.08867(7) -0.04365(16) 0.10563(6) 0.0142(2) Uani 1 1 d . . . C8 C 0.02319(8) -0.33278(19) 0.09728(9) 0.0240(3) Uani 1 1 d . . . C9 C 0.21743(7) 0.04902(15) -0.06503(7) 0.0149(2) Uani 1 1 d . . . C10 C 0.13597(9) 0.1325(2) -0.20072(7) 0.0243(3) Uani 1 1 d . . . H3 H 0.3647(10) -0.118(2) 0.0574(9) 0.023(4) Uiso 1 1 d . . . H4 H 0.4470(11) -0.207(2) 0.1828(10) 0.027(4) Uiso 1 1 d . . . H5 H 0.3960(10) -0.189(2) 0.2745(10) 0.027(4) Uiso 1 1 d . . . H6 H 0.2662(11) -0.075(2) 0.2421(10) 0.028(4) Uiso 1 1 d . . . H8A H 0.0062(10) -0.323(2) 0.1384(10) 0.027(4) Uiso 1 1 d . . . H10A H 0.0794(14) 0.145(3) -0.2335(12) 0.052(6) Uiso 1 1 d . . . H8B H 0.0380(13) -0.454(3) 0.0948(12) 0.048(6) Uiso 1 1 d . . . H10B H 0.1532(12) 0.028(3) -0.2213(11) 0.044(5) Uiso 1 1 d . . . H8C H -0.0226(12) -0.303(3) 0.0485(11) 0.039(5) Uiso 1 1 d . . . H10C H 0.1686(12) 0.233(3) -0.2029(11) 0.041(5) Uiso 1 1 d . . . H1N H 0.1344(11) -0.267(2) 0.1119(10) 0.030(4) Uiso 1 1 d . . . H2N H 0.1540(10) 0.153(2) 0.1062(9) 0.025(4) Uiso 1 1 d . . . H3N H 0.1619(11) 0.026(2) -0.0035(9) 0.025(4) Uiso 1 1 d . . . H4N H 0.1032(12) 0.079(2) -0.1174(10) 0.030(5) 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 S1 0.01219(14) 0.02113(15) 0.01755(14) -0.00233(10) 0.00729(11) 0.00167(10) S2 0.01638(15) 0.01756(15) 0.02491(16) 0.00111(11) 0.01317(12) 0.00027(11) N1 0.0128(5) 0.0175(5) 0.0229(5) -0.0006(4) 0.0088(4) -0.0001(4) N2 0.0125(5) 0.0155(5) 0.0199(5) 0.0019(4) 0.0089(4) 0.0014(4) N3 0.0119(5) 0.0251(5) 0.0157(5) 0.0010(4) 0.0071(4) 0.0029(4) N4 0.0146(5) 0.0285(6) 0.0160(5) 0.0026(4) 0.0081(4) 0.0005(4) C1 0.0115(5) 0.0153(5) 0.0174(5) -0.0005(4) 0.0070(4) -0.0004(4) C2 0.0137(5) 0.0145(5) 0.0154(5) -0.0013(4) 0.0064(4) -0.0002(4) C3 0.0147(5) 0.0224(6) 0.0202(6) -0.0013(5) 0.0088(5) 0.0021(5) C4 0.0138(5) 0.0237(6) 0.0218(6) -0.0002(5) 0.0063(5) 0.0035(5) C5 0.0164(6) 0.0248(6) 0.0170(6) 0.0037(5) 0.0043(5) 0.0030(5) C6 0.0163(5) 0.0231(6) 0.0177(6) 0.0016(4) 0.0089(5) -0.0003(5) C7 0.0131(5) 0.0196(5) 0.0104(5) -0.0003(4) 0.0057(4) 0.0000(4) C8 0.0193(6) 0.0194(6) 0.0338(7) -0.0028(5) 0.0123(6) -0.0050(5) C9 0.0155(5) 0.0136(5) 0.0174(5) -0.0022(4) 0.0088(5) -0.0012(4) C10 0.0223(6) 0.0348(7) 0.0157(6) 0.0034(5) 0.0083(5) -0.0026(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C7 1.6975(12) . ? S2 C9 1.6933(12) . ? N1 C7 1.3280(16) . ? N1 C8 1.4524(16) . ? N1 H1N 0.821(18) . ? N2 C7 1.3566(15) . ? N2 C1 1.4298(15) . ? N2 H2N 0.828(18) . ? N3 C9 1.3651(15) . ? N3 C2 1.4037(15) . ? N3 H3N 0.829(18) . ? N4 C9 1.3354(16) . ? N4 C10 1.4488(16) . ? N4 H4N 0.849(19) . ? C1 C6 1.3900(17) . ? C1 C2 1.4111(16) . ? C2 C3 1.3960(16) . ? C3 C4 1.3916(18) . ? C3 H3 0.955(17) . ? C4 C5 1.3882(18) . ? C4 H4 0.969(17) . ? C5 C6 1.3867(17) . ? C5 H5 0.913(17) . ? C6 H6 0.922(17) . ? C8 H8A 0.975(17) . ? C8 H8B 0.96(2) . ? C8 H8C 0.97(2) . ? C10 H10A 0.94(2) . ? C10 H10B 1.00(2) . ? C10 H10C 0.98(2) . ? 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 C7 N1 C8 124.19(11) . . ? C7 N1 H1N 117.8(13) . . ? C8 N1 H1N 117.1(13) . . ? C7 N2 C1 125.98(10) . . ? C7 N2 H2N 118.3(12) . . ? C1 N2 H2N 115.6(12) . . ? C9 N3 C2 133.07(11) . . ? C9 N3 H3N 115.2(12) . . ? C2 N3 H3N 111.5(12) . . ? C9 N4 C10 124.82(11) . . ? C9 N4 H4N 116.0(12) . . ? C10 N4 H4N 117.9(12) . . ? C6 C1 C2 120.66(11) . . ? C6 C1 N2 119.86(10) . . ? C2 C1 N2 119.40(10) . . ? C3 C2 N3 125.63(11) . . ? C3 C2 C1 118.43(11) . . ? N3 C2 C1 115.91(10) . . ? C4 C3 C2 119.98(11) . . ? C4 C3 H3 119.9(10) . . ? C2 C3 H3 120.1(10) . . ? C5 C4 C3 121.52(11) . . ? C5 C4 H4 120.5(10) . . ? C3 C4 H4 118.0(10) . . ? C6 C5 C4 118.84(11) . . ? C6 C5 H5 120.9(11) . . ? C4 C5 H5 120.2(11) . . ? C5 C6 C1 120.57(11) . . ? C5 C6 H6 119.5(11) . . ? C1 C6 H6 119.9(11) . . ? N1 C7 N2 117.39(10) . . ? N1 C7 S1 124.19(9) . . ? N2 C7 S1 118.42(9) . . ? N1 C8 H8A 112.3(10) . . ? N1 C8 H8B 109.5(13) . . ? H8A C8 H8B 107.7(16) . . ? N1 C8 H8C 109.2(12) . . ? H8A C8 H8C 110.1(15) . . ? H8B C8 H8C 107.9(17) . . ? N4 C9 N3 112.66(10) . . ? N4 C9 S2 122.01(9) . . ? N3 C9 S2 125.32(9) . . ? N4 C10 H10A 109.0(13) . . ? N4 C10 H10B 109.4(12) . . ? H10A C10 H10B 104.4(17) . . ? N4 C10 H10C 113.2(11) . . ? H10A C10 H10C 112.8(18) . . ? H10B C10 H10C 107.6(16) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C7 N2 C1 C6 -72.44(16) . . . . ? C7 N2 C1 C2 110.87(13) . . . . ? C9 N3 C2 C3 -16.1(2) . . . . ? C9 N3 C2 C1 165.88(12) . . . . ? C6 C1 C2 C3 -0.47(18) . . . . ? N2 C1 C2 C3 176.20(11) . . . . ? C6 C1 C2 N3 177.72(11) . . . . ? N2 C1 C2 N3 -5.61(16) . . . . ? N3 C2 C3 C4 -177.76(12) . . . . ? C1 C2 C3 C4 0.24(18) . . . . ? C2 C3 C4 C5 0.4(2) . . . . ? C3 C4 C5 C6 -0.8(2) . . . . ? C4 C5 C6 C1 0.6(2) . . . . ? C2 C1 C6 C5 0.07(19) . . . . ? N2 C1 C6 C5 -176.58(11) . . . . ? C8 N1 C7 N2 -173.80(11) . . . . ? C8 N1 C7 S1 6.48(17) . . . . ? C1 N2 C7 N1 -7.76(17) . . . . ? C1 N2 C7 S1 171.98(9) . . . . ? C10 N4 C9 N3 -176.17(12) . . . . ? C10 N4 C9 S2 4.66(18) . . . . ? C2 N3 C9 N4 -179.88(12) . . . . ? C2 N3 C9 S2 -0.7(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C4 H4 S1 0.969(17) 2.885(17) 3.5838(13) 129.8(12) 3_545 N3 H3N S1 0.829(18) 2.841(17) 3.5205(11) 140.5(15) 5 N4 H4N S1 0.849(19) 2.477(19) 3.2848(11) 159.4(16) 5 N2 H2N S2 0.828(18) 2.551(18) 3.3232(11) 155.6(15) 7 C3 H3 S2 0.955(17) 2.583(16) 3.2328(13) 125.5(12) . N1 H1N S2 0.821(18) 2.620(19) 3.3250(11) 144.9(16) 7_545 _diffrn_measured_fraction_theta_max 0.945 _diffrn_reflns_theta_full 30.34 _diffrn_measured_fraction_theta_full 0.945 _refine_diff_density_max 0.435 _refine_diff_density_min -0.249 _refine_diff_density_rms 0.055 # Attachment '- 5.CIF' data_x:\groupc~1\joelen~1\06srv2~1\frm_m _database_code_depnum_ccdc_archive 'CCDC 795074' #TrackingRef '- 5.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H22 N4 S2' _chemical_formula_sum 'C14 H22 N4 S2' _chemical_formula_weight 310.48 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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.4599(6) _cell_length_b 9.5946(6) _cell_length_c 11.0971(7) _cell_angle_alpha 78.9840(10) _cell_angle_beta 66.4850(10) _cell_angle_gamma 65.0450(10) _cell_volume 837.03(9) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.232 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 332 _exptl_absorpt_coefficient_mu 0.315 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.924 _exptl_absorpt_correction_T_max 0.963 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(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 'SMART 1k' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8785 _diffrn_reflns_av_R_equivalents 0.0439 _diffrn_reflns_av_sigmaI/netI 0.0479 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.00 _diffrn_reflns_theta_max 30.04 _reflns_number_total 4507 _reflns_number_gt 3673 _reflns_threshold_expression >2sigma(I) _computing_data_collection SMART _computing_cell_refinement SMART _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics XP _computing_publication_material XP _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^)+(0.0342P)^2^+0.4676P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4507 _refine_ls_number_parameters 181 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0531 _refine_ls_R_factor_gt 0.0392 _refine_ls_wR_factor_ref 0.0986 _refine_ls_wR_factor_gt 0.0918 _refine_ls_goodness_of_fit_ref 1.018 _refine_ls_restrained_S_all 1.018 _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 0.39540(5) 0.54798(4) 0.34386(4) 0.01968(10) Uani 1 1 d . . . S2 S -0.26011(5) 0.94895(5) 0.65841(4) 0.02222(10) Uani 1 1 d . . . N1 N 0.09372(16) 0.76393(15) 0.46540(12) 0.0183(3) Uani 1 1 d . . . H1N H 0.0277 0.8287 0.5299 0.022 Uiso 1 1 calc R . . N2 N 0.29778(17) 0.70957(15) 0.54894(13) 0.0205(3) Uani 1 1 d . . . H2N H 0.4023 0.6563 0.5425 0.025 Uiso 1 1 calc R . . N3 N -0.19003(17) 0.68085(16) 0.56058(13) 0.0217(3) Uani 1 1 d . . . H3N H -0.1979 0.5904 0.5774 0.026 Uiso 1 1 calc R . . N4 N -0.29609(18) 0.69146(17) 0.78216(13) 0.0246(3) Uani 1 1 d . . . H4N H -0.2865 0.5971 0.7780 0.029 Uiso 1 1 calc R . . C1 C 0.02309(19) 0.75434(17) 0.37740(15) 0.0180(3) Uani 1 1 d . . . C2 C 0.0934(2) 0.78229(19) 0.24272(16) 0.0220(3) Uani 1 1 d . . . H2 H 0.1860 0.8123 0.2102 0.026 Uiso 1 1 calc R . . C3 C 0.0285(2) 0.7664(2) 0.15652(16) 0.0267(4) Uani 1 1 d . . . H3 H 0.0778 0.7839 0.0649 0.032 Uiso 1 1 calc R . . C4 C -0.1088(2) 0.7248(2) 0.20420(18) 0.0295(4) Uani 1 1 d . . . H4 H -0.1515 0.7112 0.1448 0.035 Uiso 1 1 calc R . . C5 C -0.1835(2) 0.7032(2) 0.33806(17) 0.0265(4) Uani 1 1 d . . . H5 H -0.2794 0.6780 0.3703 0.032 Uiso 1 1 calc R . . C6 C -0.11890(19) 0.71808(18) 0.42615(15) 0.0198(3) Uani 1 1 d . . . C7 C 0.25212(19) 0.68330(16) 0.45940(14) 0.0168(3) Uani 1 1 d . . . C8 C -0.24803(19) 0.76678(18) 0.66759(15) 0.0198(3) Uani 1 1 d . . . C9 C 0.1938(2) 0.81731(19) 0.65737(17) 0.0264(4) Uani 1 1 d . . . H9 H 0.1101 0.9081 0.6287 0.032 Uiso 1 1 calc R . . C10 C 0.3082(3) 0.8715(2) 0.6843(2) 0.0420(5) Uani 1 1 d . . . H10A H 0.3648 0.9193 0.6041 0.063 Uiso 1 1 calc R . . H10B H 0.3914 0.7833 0.7118 0.063 Uiso 1 1 calc R . . H10C H 0.2418 0.9467 0.7542 0.063 Uiso 1 1 calc R . . C11 C 0.1010(3) 0.7410(3) 0.77769(19) 0.0419(5) Uani 1 1 d . . . H11A H 0.0303 0.7075 0.7550 0.063 Uiso 1 1 calc R . . H11B H 0.0311 0.8148 0.8486 0.063 Uiso 1 1 calc R . . H11C H 0.1818 0.6518 0.8067 0.063 Uiso 1 1 calc R . . C12 C -0.3630(2) 0.7532(2) 0.91327(16) 0.0254(3) Uani 1 1 d . . . H12 H -0.3047 0.8204 0.9107 0.030 Uiso 1 1 calc R . . C13 C -0.3214(3) 0.6183(2) 1.00801(18) 0.0373(4) Uani 1 1 d . . . H13A H -0.2003 0.5605 0.9778 0.056 Uiso 1 1 calc R . . H13B H -0.3769 0.5507 1.0114 0.056 Uiso 1 1 calc R . . H13C H -0.3601 0.6568 1.0959 0.056 Uiso 1 1 calc R . . C14 C -0.5493(2) 0.8494(2) 0.95571(18) 0.0347(4) Uani 1 1 d . . . H14A H -0.5704 0.9348 0.8923 0.052 Uiso 1 1 calc R . . H14B H -0.5890 0.8902 1.0428 0.052 Uiso 1 1 calc R . . H14C H -0.6086 0.7851 0.9594 0.052 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 0.01748(18) 0.02071(19) 0.01951(19) -0.00512(14) -0.00425(14) -0.00640(14) S2 0.0241(2) 0.01978(19) 0.02039(19) -0.00461(14) -0.00287(15) -0.00926(15) N1 0.0182(6) 0.0203(6) 0.0162(6) -0.0047(5) -0.0054(5) -0.0061(5) N2 0.0193(6) 0.0187(6) 0.0233(7) -0.0053(5) -0.0096(5) -0.0032(5) N3 0.0265(7) 0.0222(7) 0.0176(6) -0.0042(5) -0.0024(5) -0.0142(6) N4 0.0307(7) 0.0260(7) 0.0187(7) -0.0031(5) -0.0032(6) -0.0166(6) C1 0.0181(7) 0.0176(7) 0.0171(7) -0.0033(5) -0.0063(6) -0.0046(6) C2 0.0204(7) 0.0243(8) 0.0185(7) -0.0023(6) -0.0048(6) -0.0075(6) C3 0.0296(9) 0.0318(9) 0.0166(7) -0.0025(6) -0.0081(7) -0.0092(7) C4 0.0329(9) 0.0368(10) 0.0247(8) -0.0080(7) -0.0133(7) -0.0129(8) C5 0.0253(8) 0.0333(9) 0.0262(8) -0.0079(7) -0.0082(7) -0.0141(7) C6 0.0203(7) 0.0202(7) 0.0181(7) -0.0042(6) -0.0048(6) -0.0075(6) C7 0.0189(7) 0.0142(6) 0.0165(7) 0.0004(5) -0.0047(6) -0.0075(5) C8 0.0180(7) 0.0234(7) 0.0181(7) -0.0042(6) -0.0030(6) -0.0097(6) C9 0.0288(9) 0.0222(8) 0.0269(8) -0.0087(6) -0.0164(7) 0.0007(7) C10 0.0438(12) 0.0311(10) 0.0594(14) -0.0215(9) -0.0356(11) 0.0026(9) C11 0.0388(11) 0.0493(12) 0.0223(9) -0.0029(8) -0.0119(8) -0.0013(9) C12 0.0292(9) 0.0332(9) 0.0166(7) -0.0044(6) -0.0029(6) -0.0180(7) C13 0.0512(12) 0.0447(11) 0.0215(9) 0.0033(8) -0.0107(8) -0.0273(10) C14 0.0283(9) 0.0508(12) 0.0246(9) -0.0112(8) -0.0007(7) -0.0188(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 S1 C7 1.7121(15) . ? S2 C8 1.6885(16) . ? N1 C7 1.3455(19) . ? N1 C1 1.4196(19) . ? N1 H1N 0.8800 . ? N2 C7 1.3296(19) . ? N2 C9 1.469(2) . ? N2 H2N 0.8800 . ? N3 C8 1.3651(19) . ? N3 C6 1.416(2) . ? N3 H3N 0.8800 . ? N4 C8 1.345(2) . ? N4 C12 1.465(2) . ? N4 H4N 0.8800 . ? C1 C2 1.397(2) . ? C1 C6 1.400(2) . ? C2 C3 1.385(2) . ? C2 H2 0.9500 . ? C3 C4 1.391(3) . ? C3 H3 0.9500 . ? C4 C5 1.385(2) . ? C4 H4 0.9500 . ? C5 C6 1.398(2) . ? C5 H5 0.9500 . ? C9 C10 1.523(3) . ? C9 C11 1.524(3) . ? C9 H9 1.0000 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 C14 1.520(3) . ? C12 C13 1.522(3) . ? C12 H12 1.0000 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? 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 C7 N1 C1 126.11(13) . . ? C7 N1 H1N 116.9 . . ? C1 N1 H1N 116.9 . . ? C7 N2 C9 127.43(13) . . ? C7 N2 H2N 116.3 . . ? C9 N2 H2N 116.3 . . ? C8 N3 C6 128.52(13) . . ? C8 N3 H3N 115.7 . . ? C6 N3 H3N 115.7 . . ? C8 N4 C12 125.58(14) . . ? C8 N4 H4N 117.2 . . ? C12 N4 H4N 117.2 . . ? C2 C1 C6 119.83(14) . . ? C2 C1 N1 120.43(14) . . ? C6 C1 N1 119.74(14) . . ? C3 C2 C1 120.26(15) . . ? C3 C2 H2 119.9 . . ? C1 C2 H2 119.9 . . ? C2 C3 C4 119.98(15) . . ? C2 C3 H3 120.0 . . ? C4 C3 H3 120.0 . . ? C5 C4 C3 120.08(16) . . ? C5 C4 H4 120.0 . . ? C3 C4 H4 120.0 . . ? C4 C5 C6 120.55(16) . . ? C4 C5 H5 119.7 . . ? C6 C5 H5 119.7 . . ? C5 C6 C1 119.20(14) . . ? C5 C6 N3 118.32(14) . . ? C1 C6 N3 122.18(14) . . ? N2 C7 N1 117.90(13) . . ? N2 C7 S1 118.90(12) . . ? N1 C7 S1 123.19(11) . . ? N4 C8 N3 112.92(14) . . ? N4 C8 S2 123.14(12) . . ? N3 C8 S2 123.94(12) . . ? N2 C9 C10 107.41(15) . . ? N2 C9 C11 110.51(15) . . ? C10 C9 C11 112.70(17) . . ? N2 C9 H9 108.7 . . ? C10 C9 H9 108.7 . . ? C11 C9 H9 108.7 . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C9 C11 H11A 109.5 . . ? C9 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C9 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? N4 C12 C14 111.82(15) . . ? N4 C12 C13 107.77(15) . . ? C14 C12 C13 112.19(15) . . ? N4 C12 H12 108.3 . . ? C14 C12 H12 108.3 . . ? C13 C12 H12 108.3 . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C12 C14 H14A 109.5 . . ? C12 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C12 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.919 _diffrn_reflns_theta_full 30.04 _diffrn_measured_fraction_theta_full 0.919 _refine_diff_density_max 0.358 _refine_diff_density_min -0.349 _refine_diff_density_rms 0.055 # Attachment '- 6.cif' data_jws2 _database_code_depnum_ccdc_archive 'CCDC 795075' #TrackingRef '- 6.cif' _audit_creation_date 2010-09-28 _audit_creation_method ; Olex2 1.1-beta (compiled 2010.09.10 svn.r1414, GUI svn.r3225) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C9 H13 N5 S2' _chemical_formula_sum 'C9 H13 N5 S2' _chemical_formula_weight 255.36 _chemical_melting_point ? 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' _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_H-M_alt 'P -1' _space_group_name_Hall '-P 1' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, -y, -z' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 _cell_length_a 5.798(2) _cell_length_b 9.447(4) _cell_length_c 11.167(4) _cell_angle_alpha 87.646(7) _cell_angle_beta 75.043(6) _cell_angle_gamma 75.422(6) _cell_volume 571.7(4) _cell_formula_units_Z 2 _cell_measurement_reflns_used 1195 _cell_measurement_temperature 120 _cell_measurement_theta_max 27.305 _cell_measurement_theta_min 3.748 _exptl_absorpt_coefficient_mu 0.446 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.703 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'TWINABS - G.M. Sheldrick' _exptl_crystal_colour colourless _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.483 _exptl_crystal_density_meas . _exptl_crystal_density_method ? _exptl_crystal_description block _exptl_crystal_F_000 268 _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.01 _exptl_special_details ; The data collection nominally covered a full sphere of reciprocal space by a combination of 4 sets of \w scans each set at different \f and/or 2\q angles and each scan (60.00 s exposure) covering -0.300\ degrees in \w. The crystal to detector distance was 6.85 cm. The crystal was non-merohedrally twinned with the primary and secondary components in the ration of 62.4 and 37.6 percent. The data were reduced using the two orientation matrices and postprocessed using TWINABS to extract both hklf4 and hklf5 files the first for structure solution the second for final refinement. The Rint value listed in this file is output from TWINABS after parameter refinement. The number for _diffrn_reflns_number is also taken from the TWINABS output as the number of unique reflections used for structure solution - hklf4. The total number of reflections for final refinement included all overlaps and reflections from the second component giving rise to the alert B and C from checkcif. ; _diffrn_ambient_temperature 120 _diffrn_detector 'CCD area detector' _diffrn_detector_area_resol_mean 5.6 _diffrn_detector_type 'Bruker SMART CCD 6000 area detector' _diffrn_measured_fraction_theta_full 0.980 _diffrn_measured_fraction_theta_max 0.980 _diffrn_measurement_device 'three-circle diffractometer' _diffrn_measurement_device_type 'Bruker SMART CCD 6000 area detector' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_xray_symbol K-L~3~ _diffrn_reflns_av_R_equivalents 0.0368 _diffrn_reflns_av_sigmaI/netI 0.0421 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 2558 _diffrn_reflns_theta_full 27.50 _diffrn_reflns_theta_max 27.50 _diffrn_reflns_theta_min 1.89 _diffrn_source 'sealed X-ray tube' _diffrn_source_current 35.0 _diffrn_source_power 1.75 _diffrn_source_target Mo _diffrn_source_voltage 50.0 _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 3349 _reflns_number_total 4141 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement 'SAINT v6.45A (Bruker, 2003)' _computing_data_collection 'SMART v5.625 (Bruker, 2001)' _computing_data_reduction 'SAINT v6.45A (Bruker, 2003)' _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _refine_diff_density_max 0.539 _refine_diff_density_min -0.416 _refine_diff_density_rms 0.103 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.070 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 148 _refine_ls_number_reflns 4141 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0592 _refine_ls_R_factor_gt 0.0450 _refine_ls_restrained_S_all 1.070 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0648P)^2^+0.1918P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1149 _refine_ls_wR_factor_ref 0.1207 _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. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 S2 S 0.60515(10) 0.27014(7) 0.44085(6) 0.02011(16) Uani 1 1 d . . . S1 S -0.36992(11) 0.27382(7) 0.02977(6) 0.01998(16) Uani 1 1 d . . . N3 N 0.0103(3) 0.4960(2) 0.24885(18) 0.0150(4) Uani 1 1 d . . . N5 N 0.2119(3) 0.2574(2) 0.36542(17) 0.0152(4) Uani 1 1 d . . . H5 H 0.0785 0.3012 0.3417 0.018 Uiso 1 1 calc R . . N1 N 0.0291(3) 0.2676(2) 0.10653(17) 0.0155(4) Uani 1 1 d . . . H1 H 0.1206 0.3129 0.1347 0.019 Uiso 1 1 calc R . . N4 N 0.2794(3) 0.4879(2) 0.37468(18) 0.0166(4) Uani 1 1 d . . . H4 H 0.3564 0.5399 0.4066 0.020 Uiso 1 1 calc R . . N2 N -0.2557(3) 0.4922(2) 0.12286(17) 0.0156(4) Uani 1 1 d . . . H2 H -0.3783 0.5442 0.0945 0.019 Uiso 1 1 calc R . . C8 C 0.3504(4) 0.3396(3) 0.3895(2) 0.0152(5) Uani 1 1 d . . . C4 C -0.2526(4) 0.7224(3) 0.2070(2) 0.0174(5) Uani 1 1 d . . . H4A H -0.3810 0.7728 0.1711 0.021 Uiso 1 1 calc R . . C3 C -0.1618(4) 0.5713(3) 0.1940(2) 0.0141(5) Uani 1 1 d . . . C6 C 0.0352(4) 0.7210(3) 0.3295(2) 0.0164(5) Uani 1 1 d . . . H6 H 0.1111 0.7710 0.3741 0.020 Uiso 1 1 calc R . . C7 C 0.1029(4) 0.5692(3) 0.3165(2) 0.0146(5) Uani 1 1 d . . . C2 C -0.1856(4) 0.3461(3) 0.0906(2) 0.0154(5) Uani 1 1 d . . . C1 C 0.1208(4) 0.1116(3) 0.0800(2) 0.0195(5) Uani 1 1 d . . . H1A H 0.1246 0.0911 -0.0059 0.029 Uiso 1 1 calc R . . H1B H 0.0120 0.0595 0.1363 0.029 Uiso 1 1 calc R . . H1C H 0.2876 0.0786 0.0917 0.029 Uiso 1 1 calc R . . C9 C 0.2676(5) 0.0997(3) 0.3759(2) 0.0223(5) Uani 1 1 d . . . H9B H 0.4055 0.0545 0.3062 0.033 Uiso 1 1 calc R . . H9A H 0.1225 0.0652 0.3745 0.033 Uiso 1 1 calc R . . H9C H 0.3127 0.0727 0.4540 0.033 Uiso 1 1 calc R . . C5 C -0.1473(4) 0.7962(3) 0.2746(2) 0.0184(5) Uani 1 1 d . . . H5A H -0.2012 0.8997 0.2835 0.022 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 S2 0.0137(3) 0.0264(3) 0.0227(3) 0.0036(3) -0.0094(2) -0.0049(3) S1 0.0161(3) 0.0254(3) 0.0227(3) -0.0011(3) -0.0089(2) -0.0086(3) N3 0.0135(9) 0.0207(9) 0.0111(9) 0.0005(9) -0.0036(7) -0.0046(9) N5 0.0118(9) 0.0181(10) 0.0166(10) 0.0010(8) -0.0060(8) -0.0030(8) N1 0.0134(9) 0.0191(10) 0.0175(10) -0.0007(8) -0.0064(8) -0.0075(8) N4 0.0168(10) 0.0207(11) 0.0162(10) 0.0004(8) -0.0089(8) -0.0071(8) N2 0.0130(9) 0.0209(10) 0.0143(10) 0.0019(8) -0.0069(8) -0.0033(8) C8 0.0130(11) 0.0245(13) 0.0075(10) 0.0011(9) -0.0008(9) -0.0056(9) C4 0.0140(11) 0.0222(12) 0.0156(12) 0.0045(10) -0.0037(9) -0.0044(10) C3 0.0119(11) 0.0225(12) 0.0091(10) 0.0013(9) -0.0019(8) -0.0075(9) C6 0.0162(11) 0.0214(12) 0.0130(11) -0.0009(10) -0.0041(9) -0.0063(10) C7 0.0125(11) 0.0210(12) 0.0104(11) 0.0036(9) -0.0015(9) -0.0066(9) C2 0.0123(11) 0.0256(13) 0.0092(11) 0.0021(9) -0.0021(9) -0.0073(10) C1 0.0206(12) 0.0189(12) 0.0209(13) 0.0002(10) -0.0079(10) -0.0057(10) C9 0.0210(13) 0.0194(13) 0.0272(14) 0.0026(10) -0.0092(11) -0.0035(10) C5 0.0178(12) 0.0191(11) 0.0169(12) -0.0002(10) -0.0021(10) -0.0044(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 S2 C8 1.691(2) . ? S1 C2 1.689(2) . ? N3 C3 1.342(3) . ? N3 C7 1.333(3) . ? N5 H5 0.8800 . ? N5 C8 1.328(3) . ? N5 C9 1.449(3) . ? N1 H1 0.8800 . ? N1 C2 1.331(3) . ? N1 C1 1.450(3) . ? N4 H4 0.8800 . ? N4 C8 1.373(3) . ? N4 C7 1.401(3) . ? N2 H2 0.8800 . ? N2 C3 1.401(3) . ? N2 C2 1.372(3) . ? C4 H4A 0.9500 . ? C4 C3 1.390(3) . ? C4 C5 1.388(3) . ? C6 H6 0.9500 . ? C6 C7 1.392(3) . ? C6 C5 1.386(3) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C9 H9B 0.9800 . ? C9 H9A 0.9800 . ? C9 H9C 0.9800 . ? C5 H5A 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N3 C3 N2 117.7(2) . . ? N3 C3 C4 122.9(2) . . ? N3 C7 N4 117.7(2) . . ? N3 C7 C6 122.9(2) . . ? N5 C8 S2 122.9(2) . . ? N5 C8 N4 118.3(2) . . ? N5 C9 H9B 109.5 . . ? N5 C9 H9A 109.5 . . ? N5 C9 H9C 109.5 . . ? N1 C2 S1 122.6(2) . . ? N1 C2 N2 118.2(2) . . ? N1 C1 H1A 109.5 . . ? N1 C1 H1B 109.5 . . ? N1 C1 H1C 109.5 . . ? N4 C8 S2 118.85(17) . . ? N2 C2 S1 119.22(17) . . ? C8 N5 H5 118.1 . . ? C8 N5 C9 123.8(2) . . ? C8 N4 H4 115.1 . . ? C8 N4 C7 129.9(2) . . ? C4 C3 N2 119.3(2) . . ? C4 C5 H5A 119.5 . . ? C3 N2 H2 115.1 . . ? C3 C4 H4A 121.5 . . ? C6 C7 N4 119.4(2) . . ? C6 C5 C4 120.9(2) . . ? C6 C5 H5A 119.5 . . ? C7 N3 C3 118.69(19) . . ? C7 N4 H4 115.1 . . ? C7 C6 H6 121.4 . . ? C2 N1 H1 118.2 . . ? C2 N1 C1 123.6(2) . . ? C2 N2 H2 115.1 . . ? C2 N2 C3 129.9(2) . . ? C1 N1 H1 118.2 . . ? H1A C1 H1B 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C9 N5 H5 118.1 . . ? H9B C9 H9A 109.5 . . ? H9B C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? C5 C4 H4A 121.5 . . ? C5 C4 C3 117.1(2) . . ? C5 C6 H6 121.4 . . ? C5 C6 C7 117.3(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C8 N4 C7 N3 -11.0(3) . . . . ? C8 N4 C7 C6 170.1(2) . . . . ? C3 N3 C7 N4 178.94(19) . . . . ? C3 N3 C7 C6 -2.3(3) . . . . ? C3 N2 C2 S1 167.05(18) . . . . ? C3 N2 C2 N1 -14.3(3) . . . . ? C3 C4 C5 C6 -1.8(3) . . . . ? C7 N3 C3 N2 179.73(19) . . . . ? C7 N3 C3 C4 -1.6(3) . . . . ? C7 N4 C8 S2 168.89(18) . . . . ? C7 N4 C8 N5 -12.6(3) . . . . ? C7 C6 C5 C4 -1.6(3) . . . . ? C2 N2 C3 N3 -5.8(3) . . . . ? C2 N2 C3 C4 175.4(2) . . . . ? C1 N1 C2 S1 -3.5(3) . . . . ? C1 N1 C2 N2 177.9(2) . . . . ? C9 N5 C8 S2 -2.4(3) . . . . ? C9 N5 C8 N4 179.2(2) . . . . ? C5 C4 C3 N3 3.6(3) . . . . ? C5 C4 C3 N2 -177.8(2) . . . . ? C5 C6 C7 N3 3.8(3) . . . . ? C5 C6 C7 N4 -177.4(2) . . . . ?