####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_kok33 _database_code_depnum_ccdc_archive 'CCDC 620570' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 5-Methyl-2-dimethylamino-4-methylcarbonyl- 1-thia-6-oxa-6a\l4-seleno-3-azapentalene ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C9 H12 N2 O2 S Se' _chemical_formula_sum 'C9 H12 N2 O2 S Se' _chemical_formula_weight 291.24 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Se Se -0.0929 2.2259 '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 2(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 7.6506(8) _cell_length_b 18.5206(18) _cell_length_c 8.4687(8) _cell_angle_alpha 90.00 _cell_angle_beta 110.451(5) _cell_angle_gamma 90.00 _cell_volume 1124.33(19) _cell_formula_units_Z 4 _cell_measurement_temperature 190(2) _cell_measurement_reflns_used 4173 _cell_measurement_theta_min 1.0 _cell_measurement_theta_max 27.5 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.721 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 584 _exptl_absorpt_coefficient_mu 3.507 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4963 _exptl_absorpt_correction_T_max 0.5699 _exptl_absorpt_process_details 'HKL Scalepack (Otwinowski & Minor, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 190(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 KappaCCD _diffrn_measurement_method 'CCD phi and omega scans' _diffrn_detector_area_resol_mean 9 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13403 _diffrn_reflns_av_R_equivalents 0.0198 _diffrn_reflns_av_sigmaI/netI 0.0233 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 3.0 _diffrn_reflns_theta_max 27.5 _reflns_number_total 2517 _reflns_number_gt 2271 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor, 1997)' _computing_data_reduction 'HKL Denzo, Scalepack (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXTL v6.1 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXTL v6.1 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL v6.1 (Sheldrick, 1997)' _computing_publication_material 'SHELXTL v6.1 (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. Three low angle reflections were omitted for the final cycles of refinement due to beam-stop shadow effects. ; _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^)+(0.0230P)^2^+0.5825P] 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 2517 _refine_ls_number_parameters 140 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0267 _refine_ls_R_factor_gt 0.0224 _refine_ls_wR_factor_ref 0.0582 _refine_ls_wR_factor_gt 0.0560 _refine_ls_goodness_of_fit_ref 1.078 _refine_ls_restrained_S_all 1.078 _refine_ls_shift/su_max 0.018 _refine_ls_shift/su_mean 0.001 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 Se1 Se 0.44054(2) 0.451038(10) 0.77565(2) 0.02919(8) Uani 1 1 d . . . S1 S 0.45119(6) 0.57533(3) 0.75871(6) 0.03126(11) Uani 1 1 d . . . C1 C 0.2980(2) 0.57721(9) 0.5518(2) 0.0248(3) Uani 1 1 d . . . N2 N 0.2225(2) 0.51643(8) 0.47103(18) 0.0251(3) Uani 1 1 d . . . C3 C 0.2690(2) 0.45372(9) 0.5478(2) 0.0233(3) Uani 1 1 d . . . C4 C 0.1999(2) 0.38599(9) 0.4767(2) 0.0246(3) Uani 1 1 d . . . O5 O 0.39017(19) 0.33657(7) 0.73066(17) 0.0345(3) Uani 1 1 d . . . C5 C 0.2734(2) 0.32545(10) 0.5830(2) 0.0280(4) Uani 1 1 d . . . N6 N 0.2535(2) 0.63978(8) 0.47083(19) 0.0283(3) Uani 1 1 d . . . C7 C 0.3325(3) 0.70763(10) 0.5531(3) 0.0357(4) Uani 1 1 d . . . H7A H 0.3045 0.7131 0.6569 0.054 Uiso 1 1 calc R . . H7B H 0.2780 0.7480 0.4771 0.054 Uiso 1 1 calc R . . H7C H 0.4680 0.7072 0.5804 0.054 Uiso 1 1 calc R . . C8 C 0.1287(3) 0.64169(10) 0.2956(2) 0.0333(4) Uani 1 1 d . . . H8A H 0.1975 0.6275 0.2223 0.050 Uiso 1 1 calc R . . H8B H 0.0799 0.6907 0.2668 0.050 Uiso 1 1 calc R . . H8C H 0.0250 0.6081 0.2800 0.050 Uiso 1 1 calc R . . O9 O -0.02278(19) 0.31952(7) 0.26356(17) 0.0380(3) Uani 1 1 d . . . C9 C 0.0606(2) 0.37663(10) 0.3055(2) 0.0270(4) Uani 1 1 d . . . C10 C 0.0183(3) 0.43679(11) 0.1795(3) 0.0378(5) Uani 1 1 d . . . H10A H -0.0569 0.4182 0.0681 0.057 Uiso 1 1 calc R . . H10B H 0.1353 0.4567 0.1753 0.057 Uiso 1 1 calc R . . H10C H -0.0511 0.4748 0.2127 0.057 Uiso 1 1 calc R . . C11 C 0.2280(3) 0.24791(10) 0.5347(3) 0.0365(4) Uani 1 1 d . . . H11A H 0.3180 0.2166 0.6171 0.055 Uiso 1 1 calc R . . H11B H 0.2346 0.2394 0.4227 0.055 Uiso 1 1 calc R . . H11C H 0.1019 0.2371 0.5327 0.055 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 Se1 0.03166(12) 0.02844(11) 0.02346(11) 0.00210(7) 0.00461(8) 0.00219(7) S1 0.0337(2) 0.0278(2) 0.0272(2) -0.00302(17) 0.00420(19) -0.00277(17) C1 0.0264(8) 0.0233(8) 0.0254(9) 0.0001(6) 0.0098(7) 0.0000(6) N2 0.0285(7) 0.0205(7) 0.0252(8) 0.0008(6) 0.0080(6) 0.0000(5) C3 0.0235(8) 0.0256(9) 0.0214(8) 0.0014(6) 0.0086(7) 0.0019(6) C4 0.0265(8) 0.0228(8) 0.0261(9) 0.0009(7) 0.0113(7) 0.0009(6) O5 0.0429(7) 0.0264(7) 0.0307(7) 0.0050(5) 0.0084(6) 0.0033(6) C5 0.0310(9) 0.0251(8) 0.0307(10) 0.0022(7) 0.0141(8) 0.0021(7) N6 0.0337(8) 0.0197(7) 0.0302(8) -0.0003(6) 0.0096(6) -0.0018(6) C7 0.0428(11) 0.0216(9) 0.0425(11) -0.0031(8) 0.0147(9) -0.0033(7) C8 0.0385(10) 0.0265(9) 0.0317(10) 0.0047(7) 0.0080(8) 0.0032(7) O9 0.0413(7) 0.0272(7) 0.0403(8) -0.0053(6) 0.0079(6) -0.0052(6) C9 0.0275(9) 0.0252(8) 0.0294(9) -0.0034(7) 0.0115(7) 0.0012(7) C10 0.0401(11) 0.0324(10) 0.0311(10) 0.0009(8) 0.0001(8) -0.0042(8) C11 0.0438(11) 0.0229(9) 0.0413(11) 0.0044(8) 0.0132(9) 0.0027(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 Se1 C3 1.9182(17) . yes Se1 O5 2.1647(13) . yes Se1 S1 2.3097(6) . yes S1 C1 1.7348(18) . yes C1 N6 1.329(2) . yes C1 N2 1.339(2) . yes N2 C3 1.318(2) . yes C3 C4 1.412(2) . yes C4 C5 1.425(2) . yes C4 C9 1.479(2) . yes O5 C5 1.274(2) . yes C5 C11 1.501(3) . yes N6 C8 1.457(2) . yes N6 C7 1.461(2) . yes C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? O9 C9 1.222(2) . yes C9 C10 1.498(3) . yes 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 C3 Se1 O5 80.28(6) . . yes C3 Se1 S1 86.46(5) . . yes O5 Se1 S1 166.70(4) . . yes C1 S1 Se1 93.25(6) . . yes N6 C1 N2 118.83(16) . . yes N6 C1 S1 119.98(13) . . yes N2 C1 S1 121.19(13) . . yes C3 N2 C1 119.67(16) . . yes N2 C3 C4 125.22(16) . . yes N2 C3 Se1 119.41(13) . . yes C4 C3 Se1 115.37(12) . . yes C3 C4 C5 115.06(15) . . yes C3 C4 C9 123.79(15) . . yes C5 C4 C9 121.15(16) . . yes C5 O5 Se1 110.58(11) . . yes O5 C5 C4 118.66(16) . . yes O5 C5 C11 116.00(16) . . yes C4 C5 C11 125.32(17) . . yes C1 N6 C8 120.35(15) . . yes C1 N6 C7 121.00(16) . . yes C8 N6 C7 118.62(15) . . yes N6 C7 H7A 109.5 . . ? N6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? N6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? N6 C8 H8A 109.5 . . ? N6 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? N6 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? O9 C9 C4 120.70(17) . . yes O9 C9 C10 118.41(17) . . yes C4 C9 C10 120.89(16) . . yes 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 . . ? C5 C11 H11A 109.5 . . ? C5 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C5 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? 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 Se1 S1 C1 -0.62(7) . . . . ? O5 Se1 S1 C1 3.66(18) . . . . ? Se1 S1 C1 N6 -178.60(13) . . . . ? Se1 S1 C1 N2 1.52(14) . . . . ? N6 C1 N2 C3 178.11(15) . . . . ? S1 C1 N2 C3 -2.0(2) . . . . ? C1 N2 C3 C4 -179.90(15) . . . . ? C1 N2 C3 Se1 1.2(2) . . . . ? O5 Se1 C3 N2 -179.16(14) . . . . ? S1 Se1 C3 N2 -0.16(13) . . . . ? O5 Se1 C3 C4 1.88(12) . . . . ? S1 Se1 C3 C4 -179.12(12) . . . . ? N2 C3 C4 C5 178.86(15) . . . . ? Se1 C3 C4 C5 -2.3(2) . . . . ? N2 C3 C4 C9 -1.5(3) . . . . ? Se1 C3 C4 C9 177.38(12) . . . . ? C3 Se1 O5 C5 -1.30(12) . . . . ? S1 Se1 O5 C5 -5.6(3) . . . . ? Se1 O5 C5 C4 0.45(19) . . . . ? Se1 O5 C5 C11 179.19(12) . . . . ? C3 C4 C5 O5 1.1(2) . . . . ? C9 C4 C5 O5 -178.55(15) . . . . ? C3 C4 C5 C11 -177.53(16) . . . . ? C9 C4 C5 C11 2.8(3) . . . . ? N2 C1 N6 C8 -1.7(2) . . . . ? S1 C1 N6 C8 178.38(13) . . . . ? N2 C1 N6 C7 -179.79(16) . . . . ? S1 C1 N6 C7 0.3(2) . . . . ? C3 C4 C9 O9 -164.54(17) . . . . ? C5 C4 C9 O9 15.1(3) . . . . ? C3 C4 C9 C10 15.4(3) . . . . ? C5 C4 C9 C10 -164.94(17) . . . . ? _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 0.319 _refine_diff_density_min -0.471 _refine_diff_density_rms 0.055 data_kok43 _database_code_depnum_ccdc_archive 'CCDC 620571' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 3-Diacetylmethylidene-5-dimethylamino-3H-1,2,4-dithiazole ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C9 H12 N2 O2 S2' _chemical_formula_sum 'C9 H12 N2 O2 S2' _chemical_formula_weight 244.33 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 2(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 7.6627(8) _cell_length_b 18.4638(18) _cell_length_c 8.3775(8) _cell_angle_alpha 90.00 _cell_angle_beta 110.288(5) _cell_angle_gamma 90.00 _cell_volume 1111.74(19) _cell_formula_units_Z 4 _cell_measurement_temperature 190(2) _cell_measurement_reflns_used 4982 _cell_measurement_theta_min 1.0 _cell_measurement_theta_max 27.5 _exptl_crystal_description needle _exptl_crystal_colour orange _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.460 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 512 _exptl_absorpt_coefficient_mu 0.460 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8373 _exptl_absorpt_correction_T_max 0.9729 _exptl_absorpt_process_details 'HKL Scalepack (Otwinowski & Minor, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 190(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD phi and omega scans' _diffrn_detector_area_resol_mean 9 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 31420 _diffrn_reflns_av_R_equivalents 0.0249 _diffrn_reflns_av_sigmaI/netI 0.0251 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.8 _diffrn_reflns_theta_max 27.5 _reflns_number_total 2537 _reflns_number_gt 2138 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor, 1997)' _computing_data_reduction 'HKL Denzo, Scalepack (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXTL V6.1 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXTL V6.1 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL V6.1 (Sheldrick, 1997)' _computing_publication_material 'SHELXTL V6.1 (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^)+(0.0377P)^2^+0.4864P] 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 2537 _refine_ls_number_parameters 140 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0412 _refine_ls_R_factor_gt 0.0320 _refine_ls_wR_factor_ref 0.0845 _refine_ls_wR_factor_gt 0.0802 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.031 _refine_ls_shift/su_max 0.011 _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 0.45506(6) 0.06985(2) 0.25642(5) 0.03383(13) Uani 1 1 d . . . C1 C 0.3027(2) 0.07588(8) 0.04782(19) 0.0264(3) Uani 1 1 d . . . S2 S 0.42912(6) -0.04522(2) 0.26335(5) 0.03232(12) Uani 1 1 d . . . N2 N 0.22342(17) 0.01591(6) -0.03230(16) 0.0264(3) Uani 1 1 d . . . C3 C 0.26871(19) -0.04644(8) 0.05111(19) 0.0246(3) Uani 1 1 d . . . C4 C 0.1938(2) -0.11410(8) -0.01829(19) 0.0264(3) Uani 1 1 d . . . O5 O 0.38250(17) -0.16270(6) 0.23739(15) 0.0389(3) Uani 1 1 d . . . C5 C 0.2649(2) -0.17471(8) 0.0909(2) 0.0306(3) Uani 1 1 d . . . N6 N 0.26531(18) 0.13935(7) -0.03090(17) 0.0304(3) Uani 1 1 d . . . C7 C 0.3511(2) 0.20604(9) 0.0552(2) 0.0382(4) Uani 1 1 d . . . H7A H 0.3333 0.2095 0.1653 0.057 Uiso 1 1 calc R . . H7B H 0.2929 0.2478 -0.0152 0.057 Uiso 1 1 calc R . . H7C H 0.4844 0.2055 0.0732 0.057 Uiso 1 1 calc R . . C8 C 0.1444(2) 0.14320(9) -0.2086(2) 0.0365(4) Uani 1 1 d . . . H8A H 0.2148 0.1294 -0.2817 0.055 Uiso 1 1 calc R . . H8B H 0.0978 0.1928 -0.2356 0.055 Uiso 1 1 calc R . . H8C H 0.0393 0.1100 -0.2279 0.055 Uiso 1 1 calc R . . C9 C 0.0515(2) -0.12293(8) -0.1889(2) 0.0288(3) Uani 1 1 d . . . O9 O -0.03681(16) -0.17947(6) -0.22768(15) 0.0395(3) Uani 1 1 d . . . C10 C 0.0106(3) -0.06363(9) -0.3201(2) 0.0406(4) Uani 1 1 d . . . H10A H -0.0686 -0.0827 -0.4307 0.061 Uiso 1 1 calc R . . H10B H 0.1276 -0.0458 -0.3287 0.061 Uiso 1 1 calc R . . H10C H -0.0536 -0.0238 -0.2863 0.061 Uiso 1 1 calc R . . C11 C 0.2140(2) -0.25228(9) 0.0429(2) 0.0386(4) Uani 1 1 d . . . H11A H 0.3005 -0.2842 0.1270 0.058 Uiso 1 1 calc R . . H11B H 0.2213 -0.2619 -0.0697 0.058 Uiso 1 1 calc R . . H11C H 0.0869 -0.2613 0.0400 0.058 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 0.0346(2) 0.0317(2) 0.0301(2) -0.00341(16) 0.00481(17) -0.00319(16) C1 0.0259(7) 0.0267(7) 0.0275(8) -0.0018(6) 0.0103(6) 0.0005(6) S2 0.0343(2) 0.0317(2) 0.0268(2) 0.00251(15) 0.00520(16) 0.00220(15) N2 0.0298(6) 0.0233(6) 0.0257(6) 0.0004(5) 0.0093(5) 0.0001(5) C3 0.0241(7) 0.0270(8) 0.0244(7) 0.0015(6) 0.0105(6) 0.0028(5) C4 0.0294(7) 0.0236(7) 0.0291(8) 0.0005(6) 0.0138(6) 0.0016(6) O5 0.0465(7) 0.0319(6) 0.0343(6) 0.0066(5) 0.0090(5) 0.0040(5) C5 0.0328(8) 0.0282(8) 0.0346(9) 0.0024(6) 0.0167(7) 0.0029(6) N6 0.0363(7) 0.0222(6) 0.0330(7) -0.0008(5) 0.0124(6) -0.0016(5) C7 0.0431(9) 0.0259(8) 0.0467(10) -0.0055(7) 0.0170(8) -0.0051(7) C8 0.0422(9) 0.0284(8) 0.0354(9) 0.0055(7) 0.0089(7) 0.0032(7) C9 0.0286(7) 0.0269(8) 0.0325(8) -0.0039(6) 0.0127(6) 0.0020(6) O9 0.0411(7) 0.0282(6) 0.0453(7) -0.0048(5) 0.0101(6) -0.0047(5) C10 0.0433(10) 0.0367(9) 0.0323(9) 0.0014(7) 0.0013(7) -0.0036(7) C11 0.0446(9) 0.0256(8) 0.0456(10) 0.0057(7) 0.0158(8) 0.0028(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 C1 1.7361(15) . yes S1 S2 2.1367(6) . yes C1 N6 1.326(2) . yes C1 N2 1.3279(19) . yes S2 C3 1.7768(15) . yes N2 C3 1.3288(19) . yes C3 C4 1.413(2) . yes C4 C5 1.428(2) . yes C4 C9 1.476(2) . yes O5 C5 1.265(2) . yes C5 C11 1.502(2) . yes N6 C8 1.457(2) . yes N6 C7 1.463(2) . yes C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 O9 1.2253(19) . yes C9 C10 1.505(2) . yes 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 C1 S1 S2 93.14(5) . . yes N6 C1 N2 120.22(14) . . yes N6 C1 S1 120.74(11) . . yes N2 C1 S1 119.05(12) . . yes C3 S2 S1 91.37(5) . . yes C1 N2 C3 117.79(13) . . yes N2 C3 C4 123.70(14) . . yes N2 C3 S2 118.64(11) . . yes C4 C3 S2 117.66(11) . . yes C3 C4 C5 114.76(13) . . yes C3 C4 C9 123.67(13) . . yes C5 C4 C9 121.57(13) . . yes O5 C5 C4 117.98(14) . . yes O5 C5 C11 117.30(14) . . yes C4 C5 C11 124.70(15) . . yes C1 N6 C8 120.15(13) . . yes C1 N6 C7 121.05(14) . . yes C8 N6 C7 118.73(13) . . yes N6 C7 H7A 109.5 . . ? N6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? N6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? N6 C8 H8A 109.5 . . ? N6 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? N6 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? O9 C9 C4 120.38(14) . . yes O9 C9 C10 118.04(14) . . yes C4 C9 C10 121.58(13) . . yes 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 . . ? C5 C11 H11A 109.5 . . ? C5 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C5 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? 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 S2 S1 C1 N6 -178.72(12) . . . . ? S2 S1 C1 N2 1.42(12) . . . . ? C1 S1 S2 C3 -0.80(7) . . . . ? N6 C1 N2 C3 178.60(13) . . . . ? S1 C1 N2 C3 -1.54(19) . . . . ? C1 N2 C3 C4 179.50(13) . . . . ? C1 N2 C3 S2 0.68(19) . . . . ? S1 S2 C3 N2 0.26(12) . . . . ? S1 S2 C3 C4 -178.63(11) . . . . ? N2 C3 C4 C5 178.36(13) . . . . ? S2 C3 C4 C5 -2.82(18) . . . . ? N2 C3 C4 C9 -2.4(2) . . . . ? S2 C3 C4 C9 176.41(11) . . . . ? C3 C4 C5 O5 1.4(2) . . . . ? C9 C4 C5 O5 -177.86(13) . . . . ? C3 C4 C5 C11 -176.92(14) . . . . ? C9 C4 C5 C11 3.8(2) . . . . ? N2 C1 N6 C8 -3.2(2) . . . . ? S1 C1 N6 C8 176.99(11) . . . . ? N2 C1 N6 C7 179.92(13) . . . . ? S1 C1 N6 C7 0.1(2) . . . . ? C3 C4 C9 O9 -164.03(14) . . . . ? C5 C4 C9 O9 15.1(2) . . . . ? C3 C4 C9 C10 16.2(2) . . . . ? C5 C4 C9 C10 -164.62(15) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.315 _refine_diff_density_min -0.215 _refine_diff_density_rms 0.047 data_kok44 _database_code_depnum_ccdc_archive 'CCDC 620572' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'Thiocarbamate thioanhydride' _chemical_melting_point ? _chemical_formula_moiety 'C6 H12 N2 S1.97 Se1.03' _chemical_formula_sum 'C6 H12 N2 S1.97 Se1.03' _chemical_formula_weight 256.50 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' Se Se -0.0929 2.2259 '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 2(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 10.1624(10) _cell_length_b 7.4766(7) _cell_length_c 14.1240(14) _cell_angle_alpha 90.00 _cell_angle_beta 111.027(5) _cell_angle_gamma 90.00 _cell_volume 1001.68(17) _cell_formula_units_Z 4 _cell_measurement_temperature 190(2) _cell_measurement_reflns_used 4452 _cell_measurement_theta_min 1.0 _cell_measurement_theta_max 27.5 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.41 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.701 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 514 _exptl_absorpt_coefficient_mu 4.211 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2595 _exptl_absorpt_correction_T_max 0.5534 _exptl_absorpt_process_details 'HKL Scalepack (Otwinowski & Minor, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 190(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 KappaCCD _diffrn_measurement_method 'CCD phi and omega scans' _diffrn_detector_area_resol_mean 9 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 29933 _diffrn_reflns_av_R_equivalents 0.0180 _diffrn_reflns_av_sigmaI/netI 0.0175 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.1 _diffrn_reflns_theta_max 27.5 _reflns_number_total 2293 _reflns_number_gt 2113 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor, 1997)' _computing_data_reduction 'HKL Denzo, Scalepack (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXTL v6.1 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXTL v6.1 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL v6.1 (Sheldrick, 1997)' _computing_publication_material 'SHELXTL v6.1 (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^)+(0.0082P)^2^+0.8003P] 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 SHELXL _refine_ls_extinction_coef 0.0043(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2293 _refine_ls_number_parameters 108 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0277 _refine_ls_R_factor_gt 0.0236 _refine_ls_wR_factor_ref 0.0486 _refine_ls_wR_factor_gt 0.0475 _refine_ls_goodness_of_fit_ref 1.143 _refine_ls_restrained_S_all 1.143 _refine_ls_shift/su_max 0.006 _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 N1 N 0.86069(16) 0.6736(2) 0.12257(11) 0.0258(4) Uani 1 1 d . . . S2 S 0.79456(3) 0.32008(4) 0.07837(3) 0.03369(12) Uani 0.559(3) 1 d P . . Se2 Se 0.79456(3) 0.32008(4) 0.07837(3) 0.03369(12) Uani 0.441(3) 1 d P . . C2 C 0.77210(18) 0.5401(2) 0.11407(13) 0.0240(4) Uani 1 1 d . . . S3 S 0.59638(3) 0.58946(4) 0.12475(2) 0.02761(12) Uani 0.661(3) 1 d P . . Se3 Se 0.59638(3) 0.58946(4) 0.12475(2) 0.02761(12) Uani 0.339(3) 1 d P . . S4 S 0.82027(4) 0.60089(5) 0.34831(3) 0.03330(14) Uani 0.751(3) 1 d P . . Se4 Se 0.82027(4) 0.60089(5) 0.34831(3) 0.03330(14) Uani 0.249(3) 1 d P . . C4 C 0.64832(18) 0.6057(2) 0.26455(13) 0.0241(4) Uani 1 1 d . . . N5 N 0.53549(16) 0.6190(2) 0.29197(12) 0.0271(4) Uani 1 1 d . . . C6 C 0.9955(2) 0.6438(3) 0.10909(17) 0.0360(5) Uani 1 1 d . . . H6A H 1.0206 0.5169 0.1193 0.054 Uiso 1 1 calc R . . H6B H 1.0691 0.7155 0.1586 0.054 Uiso 1 1 calc R . . H6C H 0.9870 0.6793 0.0403 0.054 Uiso 1 1 calc R . . C7 C 0.8392(2) 0.8602(3) 0.14547(17) 0.0370(5) Uani 1 1 d . . . H7A H 0.7439 0.8745 0.1465 0.056 Uiso 1 1 calc R . . H7B H 0.8509 0.9383 0.0933 0.056 Uiso 1 1 calc R . . H7C H 0.9085 0.8925 0.2119 0.056 Uiso 1 1 calc R . . C8 C 0.38983(19) 0.6206(3) 0.21937(16) 0.0336(5) Uani 1 1 d . . . H8A H 0.3848 0.6914 0.1598 0.050 Uiso 1 1 calc R . . H8B H 0.3280 0.6737 0.2514 0.050 Uiso 1 1 calc R . . H8C H 0.3594 0.4978 0.1984 0.050 Uiso 1 1 calc R . . C9 C 0.5542(2) 0.6181(3) 0.39980(15) 0.0376(5) Uani 1 1 d . . . H9A H 0.5869 0.4998 0.4286 0.056 Uiso 1 1 calc R . . H9B H 0.4641 0.6452 0.4073 0.056 Uiso 1 1 calc R . . H9C H 0.6241 0.7086 0.4357 0.056 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 N1 0.0258(8) 0.0269(8) 0.0271(8) -0.0014(6) 0.0125(6) -0.0011(6) S2 0.03130(18) 0.02452(17) 0.0500(2) -0.00338(13) 0.02030(14) -0.00116(11) Se2 0.03130(18) 0.02452(17) 0.0500(2) -0.00338(13) 0.02030(14) -0.00116(11) C2 0.0232(9) 0.0283(9) 0.0216(8) 0.0008(7) 0.0093(7) 0.0012(7) S3 0.02388(17) 0.0381(2) 0.02280(17) -0.00368(13) 0.01072(12) -0.00023(12) Se3 0.02388(17) 0.0381(2) 0.02280(17) -0.00368(13) 0.01072(12) -0.00023(12) S4 0.0255(2) 0.0461(3) 0.0265(2) -0.00308(15) 0.00713(14) 0.00578(15) Se4 0.0255(2) 0.0461(3) 0.0265(2) -0.00308(15) 0.00713(14) 0.00578(15) C4 0.0258(9) 0.0210(9) 0.0260(9) -0.0011(7) 0.0100(7) 0.0018(7) N5 0.0240(8) 0.0299(8) 0.0289(8) -0.0004(7) 0.0112(6) 0.0031(6) C6 0.0278(10) 0.0392(11) 0.0462(12) -0.0009(9) 0.0194(9) -0.0034(8) C7 0.0395(11) 0.0266(10) 0.0470(13) -0.0067(9) 0.0181(10) -0.0026(8) C8 0.0238(9) 0.0375(11) 0.0403(11) 0.0010(9) 0.0126(8) 0.0018(8) C9 0.0394(11) 0.0472(13) 0.0317(11) 0.0020(9) 0.0196(9) 0.0070(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 N1 C2 1.321(2) . yes N1 C7 1.466(2) . yes N1 C6 1.466(2) . yes S2 C2 1.7593(18) . yes C2 S3 1.8818(17) . yes S3 C4 1.8559(18) . yes S4 C4 1.7236(18) . yes C4 N5 1.339(2) . yes N5 C9 1.466(2) . yes N5 C8 1.467(2) . yes C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 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 C2 N1 C7 126.07(16) . . yes C2 N1 C6 120.78(16) . . yes C7 N1 C6 113.15(15) . . yes N1 C2 S2 125.35(13) . . yes N1 C2 S3 118.69(13) . . yes S2 C2 S3 115.51(10) . . yes C4 S3 C2 100.50(8) . . yes N5 C4 S4 124.43(14) . . yes N5 C4 S3 111.49(13) . . yes S4 C4 S3 124.07(10) . . yes C4 N5 C9 119.67(16) . . yes C4 N5 C8 123.51(16) . . yes C9 N5 C8 116.64(15) . . yes N1 C6 H6A 109.5 . . ? N1 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? N1 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? N1 C7 H7A 109.5 . . ? N1 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? N1 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? N5 C8 H8A 109.5 . . ? N5 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? N5 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? N5 C9 H9A 109.5 . . ? N5 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? N5 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? 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 N1 C2 S2 175.58(15) . . . . ? C6 N1 C2 S2 -4.5(3) . . . . ? C7 N1 C2 S3 3.6(3) . . . . ? C6 N1 C2 S3 -176.51(14) . . . . ? N1 C2 S3 C4 -79.45(15) . . . . ? S2 C2 S3 C4 107.77(10) . . . . ? C2 S3 C4 N5 -172.31(13) . . . . ? C2 S3 C4 S4 6.85(13) . . . . ? S4 C4 N5 C9 -4.3(3) . . . . ? S3 C4 N5 C9 174.89(14) . . . . ? S4 C4 N5 C8 -179.22(14) . . . . ? S3 C4 N5 C8 -0.1(2) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.266 _refine_diff_density_min -0.300 _refine_diff_density_rms 0.050