# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2005 data_global _journal_coden_Cambridge 182 _journal_volume ? _journal_year ? _journal_page_first ? _publ_requested_journal 'Chemical Communications' loop_ _publ_author_name 'Richard Oakley' 'Leanne Beer' 'Robert C. Haddon' 'Mikhail E. Itkis' 'Alicea A. Leitch' 'Robert W. Reed' 'John F. Richardson' 'Donald G. VanderVeer' _publ_contact_author_name 'Richard Oakley' _publ_contact_author_address ; Department of Chemistry University of Waterloo Waterloo Ontario N2L 3G1 CANADA ; _publ_contact_author_email OAKLEY@SCIBORG.UWATERLOO.CA _publ_section_title ; Resonance stabilized bis-thiadiazinyl radicals ; data_rto14rtb _database_code_depnum_ccdc_archive 'CCDC 256271' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 10-chloro-5-ethyl-3,7-diphenyl-5H-[1,2,4]thiadiazino [6',5':5,6]pyrido[2,3-e][1,2,4]thiadiazin-1-ium triflate ; _chemical_name_common '[PhClBTMe][OTf]' _chemical_melting_point 273 _chemical_formula_moiety 'C21 H13 Cl F3 N5 O3 S3' _chemical_formula_sum 'C21 H13 Cl F3 N5 O3 S3' _chemical_formula_weight 571.99 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' F F 0.0171 0.0103 '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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pbca _symmetry_space_group_name_Hall -P2ac2ab loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 8.4474(6) _cell_length_b 13.9712(10) _cell_length_c 40.105(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4733.2(6) _cell_formula_units_Z 8 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 7065 _cell_measurement_theta_min 2.41 _cell_measurement_theta_max 26.19 _exptl_crystal_description plate _exptl_crystal_colour purple _exptl_crystal_size_max 0.417 _exptl_crystal_size_mid 0.311 _exptl_crystal_size_min 0.117 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.605 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2320 _exptl_absorpt_coefficient_mu 0.486 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.816 _exptl_absorpt_correction_T_max 0.940 _exptl_absorpt_process_details 'SADABS (George Sheldrick)' _exptl_special_details ; Data were collected with a Bruker SMART APEX CCD-based diffractometer using /w-scans of width 0.3 deg. and 30s duration at a crystal-to-detector distance of 4.908 cm. Intensity decay over the course of the data collection was evaluated by recollecting the first 50 frames of data at the end of the experiment. No significant decay was noted. ; _diffrn_ambient_temperature 295(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 APEX' _diffrn_measurement_method /w-scans _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% <0.1 _diffrn_reflns_number 39098 _diffrn_reflns_av_R_equivalents 0.0288 _diffrn_reflns_av_sigmaI/netI 0.0300 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -52 _diffrn_reflns_limit_l_max 51 _diffrn_reflns_theta_min 2.03 _diffrn_reflns_theta_max 27.95 _reflns_number_total 5591 _reflns_number_gt 4165 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART 5.625 (Bruker, 2001)' _computing_cell_refinement 'SAINT 6.22 (Bruker, 2001)' _computing_data_reduction 'SAINT 6.22 (Bruker, 2001)' _computing_structure_solution 'SHELXS-90 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL 6.12 (Bruker, 2001)' _computing_publication_material 'SHELXTL 6.12 (Bruker, 2001)' _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^)+(0.0883P)^2^+3.8145P] 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 5591 _refine_ls_number_parameters 326 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0782 _refine_ls_R_factor_gt 0.0587 _refine_ls_wR_factor_ref 0.1745 _refine_ls_wR_factor_gt 0.1615 _refine_ls_goodness_of_fit_ref 1.018 _refine_ls_restrained_S_all 1.018 _refine_ls_shift/su_max 0.003 _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 -0.01351(11) 1.13005(6) 0.18057(2) 0.0648(3) Uani 1 1 d . . . S2 S -0.16908(10) 1.10559(5) 0.05091(2) 0.0563(2) Uani 1 1 d . . . Cl1 Cl -0.10983(11) 1.23289(5) 0.11468(2) 0.0686(3) Uani 1 1 d . . . N1 N -0.0776(3) 0.90004(16) 0.06101(6) 0.0456(5) Uani 1 1 d . . . N2 N -0.1793(3) 1.02007(18) 0.02401(6) 0.0564(6) Uani 1 1 d . . . N3 N -0.0096(2) 0.91668(15) 0.11585(5) 0.0408(5) Uani 1 1 d . . . N4 N 0.0588(3) 0.92127(16) 0.17084(6) 0.0464(5) Uani 1 1 d . . . N5 N 0.0511(4) 1.0543(2) 0.20844(7) 0.0633(7) Uani 1 1 d . . . C1 C -0.0632(3) 0.95669(18) 0.08656(6) 0.0406(5) Uani 1 1 d . . . C2 C -0.1349(3) 0.9321(2) 0.03120(7) 0.0470(6) Uani 1 1 d . . . C3 C -0.0985(3) 1.05722(19) 0.08655(7) 0.0454(6) Uani 1 1 d . . . C4 C -0.0766(3) 1.11162(19) 0.11493(7) 0.0485(6) Uani 1 1 d . . . C5 C -0.0283(3) 1.06858(19) 0.14400(7) 0.0462(6) Uani 1 1 d . . . C6 C 0.0087(3) 0.96776(19) 0.14494(7) 0.0428(6) Uani 1 1 d . . . C7 C 0.0800(3) 0.9652(2) 0.20115(7) 0.0515(7) Uani 1 1 d . . . C8 C -0.1460(3) 0.8598(2) 0.00432(7) 0.0495(6) Uani 1 1 d . . . C9 C -0.0836(4) 0.7692(2) 0.00897(8) 0.0561(7) Uani 1 1 d . . . H9 H -0.0365 0.7531 0.0292 0.067 Uiso 1 1 calc R . . C10 C -0.0914(4) 0.7023(3) -0.01656(8) 0.0645(8) Uani 1 1 d . . . H10 H -0.0482 0.6417 -0.0135 0.077 Uiso 1 1 calc R . . C11 C -0.1630(4) 0.7253(3) -0.04635(9) 0.0675(9) Uani 1 1 d . . . H11 H -0.1688 0.6801 -0.0633 0.081 Uiso 1 1 calc R . . C12 C -0.2258(4) 0.8151(3) -0.05104(8) 0.0671(9) Uani 1 1 d . . . H12 H -0.2742 0.8304 -0.0712 0.081 Uiso 1 1 calc R . . C13 C -0.2174(4) 0.8827(2) -0.02601(8) 0.0589(7) Uani 1 1 d . . . H13 H -0.2593 0.9435 -0.0294 0.071 Uiso 1 1 calc R . . C14 C 0.1439(3) 0.9043(2) 0.22811(7) 0.0525(7) Uani 1 1 d . . . C15 C 0.1437(4) 0.9359(3) 0.26084(8) 0.0677(9) Uani 1 1 d . . . H15 H 0.1027 0.9959 0.2660 0.081 Uiso 1 1 calc R . . C16 C 0.2039(5) 0.8792(3) 0.28578(9) 0.0765(10) Uani 1 1 d . . . H16 H 0.2016 0.9006 0.3077 0.092 Uiso 1 1 calc R . . C17 C 0.2665(4) 0.7922(3) 0.27873(9) 0.0722(9) Uani 1 1 d . . . H17 H 0.3085 0.7546 0.2957 0.087 Uiso 1 1 calc R . . C18 C 0.2678(5) 0.7598(3) 0.24634(10) 0.0787(10) Uani 1 1 d . . . H18 H 0.3113 0.7004 0.2414 0.094 Uiso 1 1 calc R . . C19 C 0.2050(5) 0.8150(3) 0.22125(8) 0.0702(9) Uani 1 1 d . . . H19 H 0.2037 0.7920 0.1995 0.084 Uiso 1 1 calc R . . C20 C 0.0323(4) 0.8139(2) 0.11654(7) 0.0536(7) Uani 1 1 d . . . H20A H 0.1431 0.8071 0.1213 0.080 Uiso 1 1 calc R . . H20B H 0.0094 0.7858 0.0953 0.080 Uiso 1 1 calc R . . H20C H -0.0284 0.7822 0.1335 0.080 Uiso 1 1 calc R . . C21 C 0.4555(4) 0.0556(3) 0.15308(11) 0.0800(11) Uani 1 1 d . . . F1 F 0.5867(4) 0.0967(3) 0.16435(8) 0.1388(13) Uani 1 1 d . . . F2 F 0.3421(3) 0.1195(2) 0.15288(9) 0.1182(10) Uani 1 1 d . . . F3 F 0.4145(4) -0.0110(3) 0.17433(8) 0.1435(14) Uani 1 1 d . . . S3 S 0.48675(10) 0.00748(6) 0.11163(3) 0.0721(3) Uani 1 1 d . . . O1 O 0.5273(3) 0.0936(2) 0.09352(8) 0.0884(8) Uani 1 1 d . . . O2 O 0.3353(4) -0.0326(3) 0.10390(9) 0.1169(13) Uani 1 1 d . . . O3 O 0.6170(4) -0.0570(2) 0.11647(13) 0.1368(17) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0801(6) 0.0506(4) 0.0638(5) -0.0188(4) -0.0040(4) 0.0111(4) S2 0.0631(5) 0.0474(4) 0.0583(4) 0.0069(3) 0.0011(3) 0.0041(3) Cl1 0.0801(6) 0.0409(4) 0.0846(6) -0.0031(4) 0.0057(4) 0.0065(4) N1 0.0448(12) 0.0448(12) 0.0473(12) -0.0008(10) 0.0028(9) -0.0018(10) N2 0.0588(14) 0.0557(14) 0.0547(14) 0.0051(11) -0.0010(12) -0.0009(12) N3 0.0398(11) 0.0377(11) 0.0449(12) -0.0037(9) 0.0043(9) 0.0001(8) N4 0.0479(12) 0.0464(12) 0.0447(12) -0.0059(10) 0.0036(10) 0.0013(10) N5 0.0732(17) 0.0613(16) 0.0556(15) -0.0163(13) -0.0029(13) 0.0029(14) C1 0.0350(12) 0.0409(12) 0.0460(14) 0.0013(11) 0.0057(10) -0.0034(10) C2 0.0404(13) 0.0541(15) 0.0465(14) 0.0026(12) 0.0032(11) -0.0052(12) C3 0.0379(13) 0.0425(13) 0.0558(15) 0.0017(12) 0.0086(11) -0.0027(10) C4 0.0473(15) 0.0363(12) 0.0620(17) -0.0009(12) 0.0072(13) 0.0019(11) C5 0.0406(13) 0.0415(13) 0.0564(16) -0.0100(12) 0.0069(11) -0.0004(11) C6 0.0372(12) 0.0422(13) 0.0490(14) -0.0061(11) 0.0078(11) -0.0018(10) C7 0.0480(15) 0.0552(16) 0.0514(16) -0.0076(13) 0.0060(12) -0.0021(13) C8 0.0427(14) 0.0583(16) 0.0476(15) -0.0019(12) 0.0025(11) -0.0076(12) C9 0.0587(17) 0.0583(17) 0.0512(16) -0.0031(13) -0.0029(13) -0.0052(14) C10 0.069(2) 0.0607(18) 0.064(2) -0.0081(15) -0.0025(16) -0.0072(16) C11 0.065(2) 0.078(2) 0.0594(19) -0.0155(17) -0.0003(16) -0.0155(18) C12 0.0613(19) 0.089(2) 0.0510(17) -0.0045(17) -0.0096(15) -0.0127(18) C13 0.0507(17) 0.0680(19) 0.0579(17) -0.0011(15) -0.0040(13) -0.0028(14) C14 0.0481(15) 0.0602(17) 0.0490(15) -0.0041(13) 0.0030(12) -0.0047(13) C15 0.073(2) 0.074(2) 0.0559(18) -0.0097(16) -0.0045(16) -0.0013(18) C16 0.078(2) 0.101(3) 0.0499(18) -0.0020(18) -0.0060(17) -0.007(2) C17 0.063(2) 0.091(3) 0.063(2) 0.0152(19) -0.0006(16) -0.0031(19) C18 0.092(3) 0.073(2) 0.071(2) 0.0083(18) 0.004(2) 0.017(2) C19 0.087(3) 0.073(2) 0.0513(17) -0.0032(16) 0.0050(17) 0.0106(19) C20 0.0723(19) 0.0382(13) 0.0502(16) -0.0063(11) -0.0033(14) 0.0059(13) C21 0.054(2) 0.090(3) 0.096(3) 0.013(2) -0.0062(19) -0.0159(19) F1 0.093(2) 0.201(4) 0.122(2) -0.024(2) -0.0138(17) -0.061(2) F2 0.0917(19) 0.115(2) 0.148(3) -0.0311(19) 0.0338(18) 0.0079(17) F3 0.094(2) 0.215(4) 0.121(2) 0.074(2) -0.0061(17) -0.040(2) S3 0.0506(5) 0.0562(5) 0.1094(8) -0.0130(5) 0.0178(4) -0.0089(4) O1 0.0737(17) 0.091(2) 0.100(2) 0.0236(17) 0.0146(15) -0.0031(14) O2 0.0773(19) 0.133(3) 0.140(3) -0.061(2) 0.0210(18) -0.046(2) O3 0.076(2) 0.0477(14) 0.286(5) 0.002(2) 0.064(3) 0.0080(13) _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 N5 1.633(3) . no S1 C5 1.704(3) . no S2 N2 1.612(3) . no S2 C3 1.690(3) . no Cl1 C4 1.717(3) . no N1 C1 1.301(3) . no N1 C2 1.365(4) . no N2 C2 1.317(4) . no N3 C6 1.376(3) . no N3 C1 1.378(3) . no N3 C20 1.479(3) . no N4 C6 1.296(4) . no N4 C7 1.374(4) . no N5 C7 1.302(4) . no C1 C3 1.436(4) . no C2 C8 1.480(4) . no C3 C4 1.381(4) . no C4 C5 1.374(4) . no C5 C6 1.443(4) . no C7 C14 1.477(4) . no C8 C9 1.384(4) . no C8 C13 1.395(4) . no C9 C10 1.388(4) . no C9 H9 0.9300 . no C10 C11 1.377(5) . no C10 H10 0.9300 . no C11 C12 1.375(5) . no C11 H11 0.9300 . no C12 C13 1.380(5) . no C12 H12 0.9300 . no C13 H13 0.9300 . no C14 C19 1.378(5) . no C14 C15 1.385(4) . no C15 C16 1.374(5) . no C15 H15 0.9300 . no C16 C17 1.355(5) . no C16 H16 0.9300 . no C17 C18 1.376(5) . no C17 H17 0.9300 . no C18 C19 1.374(5) . no C18 H18 0.9300 . no C19 H19 0.9300 . no C20 H20A 0.9600 . no C20 H20B 0.9600 . no C20 H20C 0.9600 . no C21 F3 1.308(5) . no C21 F2 1.310(5) . no C21 F1 1.327(4) . no C21 S3 1.812(5) . no S3 O2 1.431(3) . no S3 O3 1.435(3) . no S3 O1 1.446(3) . no 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 N5 S1 C5 106.67(14) . . no N2 S2 C3 106.77(13) . . no C1 N1 C2 121.6(2) . . no C2 N2 S2 122.0(2) . . no C6 N3 C1 123.3(2) . . no C6 N3 C20 117.4(2) . . no C1 N3 C20 119.3(2) . . no C6 N4 C7 121.9(2) . . no C7 N5 S1 121.9(2) . . no N1 C1 N3 117.1(2) . . no N1 C1 C3 125.1(2) . . no N3 C1 C3 117.7(2) . . no N2 C2 N1 126.8(3) . . no N2 C2 C8 117.3(3) . . no N1 C2 C8 115.9(2) . . no C4 C3 C1 120.7(3) . . no C4 C3 S2 121.6(2) . . no C1 C3 S2 117.7(2) . . no C5 C4 C3 119.9(3) . . no C5 C4 Cl1 119.0(2) . . no C3 C4 Cl1 121.1(2) . . no C4 C5 C6 120.9(2) . . no C4 C5 S1 122.1(2) . . no C6 C5 S1 117.0(2) . . no N4 C6 N3 117.1(2) . . no N4 C6 C5 125.5(2) . . no N3 C6 C5 117.4(2) . . no N5 C7 N4 127.0(3) . . no N5 C7 C14 117.0(3) . . no N4 C7 C14 116.0(3) . . no C9 C8 C13 119.5(3) . . no C9 C8 C2 120.1(3) . . no C13 C8 C2 120.4(3) . . no C8 C9 C10 119.9(3) . . no C8 C9 H9 120.0 . . no C10 C9 H9 120.0 . . no C11 C10 C9 120.2(3) . . no C11 C10 H10 119.9 . . no C9 C10 H10 119.9 . . no C12 C11 C10 120.1(3) . . no C12 C11 H11 120.0 . . no C10 C11 H11 120.0 . . no C11 C12 C13 120.3(3) . . no C11 C12 H12 119.8 . . no C13 C12 H12 119.8 . . no C12 C13 C8 120.0(3) . . no C12 C13 H13 120.0 . . no C8 C13 H13 120.0 . . no C19 C14 C15 118.6(3) . . no C19 C14 C7 120.8(3) . . no C15 C14 C7 120.6(3) . . no C16 C15 C14 120.4(4) . . no C16 C15 H15 119.8 . . no C14 C15 H15 119.8 . . no C17 C16 C15 120.7(3) . . no C17 C16 H16 119.7 . . no C15 C16 H16 119.7 . . no C16 C17 C18 119.7(4) . . no C16 C17 H17 120.2 . . no C18 C17 H17 120.2 . . no C19 C18 C17 120.3(4) . . no C19 C18 H18 119.9 . . no C17 C18 H18 119.9 . . no C18 C19 C14 120.4(3) . . no C18 C19 H19 119.8 . . no C14 C19 H19 119.8 . . no N3 C20 H20A 109.5 . . no N3 C20 H20B 109.5 . . no H20A C20 H20B 109.5 . . no N3 C20 H20C 109.5 . . no H20A C20 H20C 109.5 . . no H20B C20 H20C 109.5 . . no F3 C21 F2 107.2(4) . . no F3 C21 F1 107.9(4) . . no F2 C21 F1 108.5(4) . . no F3 C21 S3 111.9(3) . . no F2 C21 S3 110.7(3) . . no F1 C21 S3 110.6(3) . . no O2 S3 O3 118.0(2) . . no O2 S3 O1 115.4(2) . . no O3 S3 O1 114.10(18) . . no O2 S3 C21 102.35(18) . . no O3 S3 C21 102.7(2) . . no O1 S3 C21 100.77(19) . . no 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 S2 N2 C2 -1.1(3) . . . . no C5 S1 N5 C7 -0.6(3) . . . . no C2 N1 C1 N3 177.7(2) . . . . no C2 N1 C1 C3 -2.4(4) . . . . no C6 N3 C1 N1 -178.9(2) . . . . no C20 N3 C1 N1 1.6(3) . . . . no C6 N3 C1 C3 1.3(3) . . . . no C20 N3 C1 C3 -178.2(2) . . . . no S2 N2 C2 N1 0.8(4) . . . . no S2 N2 C2 C8 -178.6(2) . . . . no C1 N1 C2 N2 1.1(4) . . . . no C1 N1 C2 C8 -179.6(2) . . . . no N1 C1 C3 C4 -178.9(2) . . . . no N3 C1 C3 C4 1.0(4) . . . . no N1 C1 C3 S2 1.8(3) . . . . no N3 C1 C3 S2 -178.33(18) . . . . no N2 S2 C3 C4 -179.4(2) . . . . no N2 S2 C3 C1 -0.1(2) . . . . no C1 C3 C4 C5 -3.3(4) . . . . no S2 C3 C4 C5 176.0(2) . . . . no C1 C3 C4 Cl1 177.0(2) . . . . no S2 C3 C4 Cl1 -3.7(3) . . . . no C3 C4 C5 C6 3.5(4) . . . . no Cl1 C4 C5 C6 -176.9(2) . . . . no C3 C4 C5 S1 -175.0(2) . . . . no Cl1 C4 C5 S1 4.7(3) . . . . no N5 S1 C5 C4 -178.7(2) . . . . no N5 S1 C5 C6 2.8(3) . . . . no C7 N4 C6 N3 -179.5(2) . . . . no C7 N4 C6 C5 1.0(4) . . . . no C1 N3 C6 N4 179.4(2) . . . . no C20 N3 C6 N4 -1.1(4) . . . . no C1 N3 C6 C5 -1.1(4) . . . . no C20 N3 C6 C5 178.4(2) . . . . no C4 C5 C6 N4 178.2(3) . . . . no S1 C5 C6 N4 -3.3(4) . . . . no C4 C5 C6 N3 -1.3(4) . . . . no S1 C5 C6 N3 177.23(18) . . . . no S1 N5 C7 N4 -1.7(5) . . . . no S1 N5 C7 C14 177.7(2) . . . . no C6 N4 C7 N5 1.9(5) . . . . no C6 N4 C7 C14 -177.6(2) . . . . no N2 C2 C8 C9 172.2(3) . . . . no N1 C2 C8 C9 -7.2(4) . . . . no N2 C2 C8 C13 -6.9(4) . . . . no N1 C2 C8 C13 173.6(3) . . . . no C13 C8 C9 C10 0.5(5) . . . . no C2 C8 C9 C10 -178.7(3) . . . . no C8 C9 C10 C11 -0.9(5) . . . . no C9 C10 C11 C12 0.6(5) . . . . no C10 C11 C12 C13 0.1(5) . . . . no C11 C12 C13 C8 -0.5(5) . . . . no C9 C8 C13 C12 0.2(4) . . . . no C2 C8 C13 C12 179.4(3) . . . . no N5 C7 C14 C19 -168.0(3) . . . . no N4 C7 C14 C19 11.5(4) . . . . no N5 C7 C14 C15 12.0(4) . . . . no N4 C7 C14 C15 -168.5(3) . . . . no C19 C14 C15 C16 0.2(5) . . . . no C7 C14 C15 C16 -179.8(3) . . . . no C14 C15 C16 C17 1.1(6) . . . . no C15 C16 C17 C18 -1.0(6) . . . . no C16 C17 C18 C19 -0.4(6) . . . . no C17 C18 C19 C14 1.7(6) . . . . no C15 C14 C19 C18 -1.6(5) . . . . no C7 C14 C19 C18 178.4(3) . . . . no F3 C21 S3 O2 60.0(4) . . . . no F2 C21 S3 O2 -59.5(3) . . . . no F1 C21 S3 O2 -179.8(4) . . . . no F3 C21 S3 O3 -62.8(3) . . . . no F2 C21 S3 O3 177.7(3) . . . . no F1 C21 S3 O3 57.4(4) . . . . no F3 C21 S3 O1 179.2(3) . . . . no F2 C21 S3 O1 59.7(3) . . . . no F1 C21 S3 O1 -60.5(4) . . . . no _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.656 _refine_diff_density_min -0.434 _refine_diff_density_rms 0.066 data_aals _database_code_depnum_ccdc_archive 'CCDC 256272' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 10-chloro-5-methyl-3,7-diphenyl-5H-[1,2,4]thiadiazino [6',5':5,6]pyrido[2,3-e][1,2,4]thiadiazin-2-yl ; _chemical_name_common '[PhClBTMe]' _chemical_melting_point 195 _chemical_formula_moiety ? _chemical_formula_sum 'C20 H13 Cl N5 S2' _chemical_formula_weight 422.92 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' Cl Cl 0.1484 0.1585 '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/c 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 3.9232(8) _cell_length_b 27.527(6) _cell_length_c 16.378(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.17(3) _cell_angle_gamma 90.00 _cell_volume 1768.7(6) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 10985 _cell_measurement_theta_min 2.5427 _cell_measurement_theta_max 26.3714 _exptl_crystal_description needle _exptl_crystal_colour brown _exptl_crystal_size_max 0.77 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.588 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 868 _exptl_absorpt_coefficient_mu 0.470 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.6869 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173.1500 _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 ? _diffrn_measurement_method dtprofit.ref _diffrn_detector_area_resol_mean 14.6199 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 352 _diffrn_reflns_av_R_equivalents 0.0700 _diffrn_reflns_av_sigmaI/netI 0.1282 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -29 _diffrn_reflns_limit_k_max 34 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.5427 _diffrn_reflns_theta_max 26.3714 _reflns_number_total 3516 _reflns_number_gt 3025 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _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^)+(0.0825P)^2^+5.9905P] 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 3516 _refine_ls_number_parameters 253 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1108 _refine_ls_R_factor_gt 0.0983 _refine_ls_wR_factor_ref 0.2236 _refine_ls_wR_factor_gt 0.2159 _refine_ls_goodness_of_fit_ref 1.162 _refine_ls_restrained_S_all 1.162 _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 0.4367(4) 0.40079(5) 0.59673(8) 0.0340(3) Uani 1 1 d . . . S2 S -0.1948(4) 0.22907(5) 0.66863(8) 0.0339(3) Uani 1 1 d . . . Cl1 Cl 0.0980(4) 0.33064(5) 0.72494(8) 0.0403(4) Uani 1 1 d . . . N1 N -0.1143(11) 0.21409(15) 0.4855(3) 0.0277(9) Uani 1 1 d . . . C4 C 0.1213(13) 0.31323(18) 0.6238(3) 0.0267(10) Uani 1 1 d . . . N3 N 0.1751(10) 0.28531(14) 0.4625(3) 0.0261(9) Uani 1 1 d . . . C1 C 0.0095(12) 0.25445(18) 0.5166(3) 0.0270(10) Uani 1 1 d . . . C6 C 0.3136(12) 0.32959(17) 0.4859(3) 0.0248(9) Uani 1 1 d . . . N4 N 0.4687(11) 0.35467(15) 0.4285(3) 0.0290(9) Uani 1 1 d . . . C7 C 0.6008(12) 0.39989(18) 0.4441(3) 0.0282(10) Uani 1 1 d . . . N2 N -0.3293(12) 0.18249(16) 0.6126(3) 0.0321(10) Uani 1 1 d . . . C5 C 0.2784(12) 0.34466(18) 0.5689(3) 0.0267(10) Uani 1 1 d . . . C13 C -0.5634(13) 0.09993(19) 0.5352(4) 0.0328(11) Uani 1 1 d . . . H14A H -0.5928 0.1031 0.5913 0.039 Uiso 1 1 calc R . . C3 C -0.0072(13) 0.26907(18) 0.6004(3) 0.0286(10) Uani 1 1 d . . . C2 C -0.2785(12) 0.18084(18) 0.5339(3) 0.0271(10) Uani 1 1 d . . . N5 N 0.6021(12) 0.42418(16) 0.5125(3) 0.0330(10) Uani 1 1 d . . . C19 C 0.7882(13) 0.39971(19) 0.2988(3) 0.0314(11) Uani 1 1 d . . . H20A H 0.7008 0.3684 0.2939 0.038 Uiso 1 1 calc R . . C20 C 0.2001(15) 0.2706(2) 0.3764(3) 0.0357(12) Uani 1 1 d . . . H8A H 0.0933 0.2395 0.3692 0.054 Uiso 1 1 calc R . . H8B H 0.4358 0.2684 0.3612 0.054 Uiso 1 1 calc R . . H8C H 0.0878 0.2942 0.3427 0.054 Uiso 1 1 calc R . . C8 C -0.4063(12) 0.13693(18) 0.4910(3) 0.0292(11) Uani 1 1 d . . . C14 C 0.7626(13) 0.42379(18) 0.3728(3) 0.0288(10) Uani 1 1 d . . . C10 C -0.4872(14) 0.0906(2) 0.3677(3) 0.0347(11) Uani 1 1 d . . . H11A H -0.4616 0.0876 0.3115 0.042 Uiso 1 1 calc R . . C9 C -0.3704(13) 0.13232(19) 0.4067(3) 0.0314(11) Uani 1 1 d . . . H10A H -0.2688 0.1570 0.3767 0.038 Uiso 1 1 calc R . . C15 C 0.8883(14) 0.4714(2) 0.3788(4) 0.0358(12) Uani 1 1 d . . . H16A H 0.8688 0.4883 0.4277 0.043 Uiso 1 1 calc R . . C16 C 1.0412(14) 0.4931(2) 0.3123(4) 0.0369(12) Uani 1 1 d . . . H17A H 1.1244 0.5247 0.3167 0.044 Uiso 1 1 calc R . . C18 C 0.9424(14) 0.4214(2) 0.2315(3) 0.0367(12) Uani 1 1 d . . . H19A H 0.9589 0.4048 0.1822 0.044 Uiso 1 1 calc R . . C12 C -0.6759(14) 0.0584(2) 0.4953(4) 0.0377(12) Uani 1 1 d . . . H13A H -0.7761 0.0334 0.5251 0.045 Uiso 1 1 calc R . . C17 C 1.0713(14) 0.4683(2) 0.2389(3) 0.0379(13) Uani 1 1 d . . . H18A H 1.1778 0.4830 0.1946 0.045 Uiso 1 1 calc R . . C11 C -0.6396(14) 0.0538(2) 0.4107(4) 0.0384(13) Uani 1 1 d . . . H12A H -0.7178 0.0262 0.3839 0.046 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 0.0426(8) 0.0311(6) 0.0283(7) -0.0055(5) 0.0032(5) -0.0053(5) S2 0.0409(7) 0.0375(7) 0.0233(6) 0.0001(5) 0.0068(5) -0.0049(5) Cl1 0.0537(9) 0.0439(8) 0.0235(6) -0.0063(5) 0.0054(6) -0.0062(6) N1 0.030(2) 0.028(2) 0.025(2) 0.0004(16) 0.0021(16) -0.0003(16) C4 0.029(2) 0.031(2) 0.019(2) -0.0048(18) 0.0006(18) 0.0054(19) N3 0.029(2) 0.026(2) 0.023(2) -0.0026(15) 0.0036(16) 0.0022(16) C1 0.024(2) 0.030(2) 0.027(3) 0.0023(19) -0.0004(18) 0.0018(19) C6 0.023(2) 0.025(2) 0.026(2) 0.0000(18) -0.0014(18) 0.0032(18) N4 0.029(2) 0.028(2) 0.030(2) -0.0003(17) 0.0029(17) -0.0008(17) C7 0.023(2) 0.029(2) 0.033(3) -0.002(2) -0.0020(19) 0.0043(19) N2 0.037(2) 0.029(2) 0.031(2) 0.0025(17) 0.0063(18) -0.0021(18) C5 0.023(2) 0.032(2) 0.025(2) -0.0015(19) -0.0021(18) 0.0028(18) C13 0.028(3) 0.031(3) 0.040(3) 0.005(2) 0.008(2) -0.002(2) C3 0.025(2) 0.032(2) 0.029(3) 0.000(2) 0.0025(19) 0.0046(19) C2 0.022(2) 0.032(2) 0.028(2) 0.0022(19) -0.0009(18) 0.0025(19) N5 0.038(2) 0.033(2) 0.028(2) 0.0043(18) 0.0006(18) -0.0048(18) C19 0.029(3) 0.029(2) 0.036(3) 0.001(2) 0.003(2) -0.001(2) C20 0.046(3) 0.038(3) 0.023(3) -0.004(2) 0.007(2) -0.011(2) C8 0.023(2) 0.029(2) 0.035(3) 0.004(2) 0.001(2) 0.0038(19) C14 0.027(2) 0.030(2) 0.030(3) -0.001(2) -0.0039(19) 0.0003(19) C10 0.038(3) 0.035(3) 0.031(3) -0.002(2) 0.003(2) -0.001(2) C9 0.034(3) 0.030(2) 0.031(3) 0.002(2) 0.002(2) 0.002(2) C15 0.032(3) 0.035(3) 0.040(3) -0.001(2) 0.000(2) 0.001(2) C16 0.033(3) 0.030(3) 0.047(3) 0.005(2) -0.007(2) -0.006(2) C18 0.031(3) 0.050(3) 0.030(3) 0.001(2) 0.002(2) -0.002(2) C12 0.030(3) 0.035(3) 0.048(3) 0.001(2) 0.000(2) -0.004(2) C17 0.029(3) 0.050(3) 0.034(3) 0.013(2) 0.005(2) -0.001(2) C11 0.031(3) 0.028(2) 0.056(4) -0.004(2) -0.005(2) 0.000(2) _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 N5 1.657(5) . ? S1 C5 1.726(5) . ? S2 N2 1.662(5) . ? S2 C3 1.735(5) . ? Cl1 C4 1.727(5) . ? N1 C1 1.314(7) . ? N1 C2 1.372(6) . ? C4 C3 1.370(7) . ? C4 C5 1.393(7) . ? N3 C6 1.389(6) . ? N3 C1 1.390(6) . ? N3 C20 1.469(6) . ? C1 C3 1.432(7) . ? C6 N4 1.318(6) . ? C6 C5 1.427(7) . ? N4 C7 1.372(6) . ? C7 N5 1.304(7) . ? C7 C14 1.485(7) . ? N2 C2 1.305(7) . ? C13 C12 1.388(8) . ? C13 C8 1.394(7) . ? C2 C8 1.484(7) . ? C19 C14 1.385(7) . ? C19 C18 1.394(7) . ? C8 C9 1.394(7) . ? C14 C15 1.404(7) . ? C10 C11 1.372(8) . ? C10 C9 1.391(8) . ? C15 C16 1.382(8) . ? C16 C17 1.389(8) . ? C18 C17 1.391(8) . ? C12 C11 1.400(9) . ? 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 N5 S1 C5 105.6(2) . . ? N2 S2 C3 105.6(2) . . ? C1 N1 C2 120.9(4) . . ? C3 C4 C5 122.2(5) . . ? C3 C4 Cl1 119.6(4) . . ? C5 C4 Cl1 118.1(4) . . ? C6 N3 C1 122.9(4) . . ? C6 N3 C20 118.7(4) . . ? C1 N3 C20 118.4(4) . . ? N1 C1 N3 116.3(4) . . ? N1 C1 C3 126.2(5) . . ? N3 C1 C3 117.5(4) . . ? N4 C6 N3 116.3(4) . . ? N4 C6 C5 125.0(4) . . ? N3 C6 C5 118.7(4) . . ? C6 N4 C7 121.1(4) . . ? N5 C7 N4 128.7(5) . . ? N5 C7 C14 116.6(4) . . ? N4 C7 C14 114.7(4) . . ? C2 N2 S2 121.5(4) . . ? C4 C5 C6 118.6(4) . . ? C4 C5 S1 123.0(4) . . ? C6 C5 S1 118.4(4) . . ? C12 C13 C8 119.9(5) . . ? C4 C3 C1 120.0(5) . . ? C4 C3 S2 122.6(4) . . ? C1 C3 S2 117.4(4) . . ? N2 C2 N1 128.3(5) . . ? N2 C2 C8 116.3(4) . . ? N1 C2 C8 115.4(4) . . ? C7 N5 S1 121.0(4) . . ? C14 C19 C18 121.3(5) . . ? C13 C8 C9 119.6(5) . . ? C13 C8 C2 119.9(5) . . ? C9 C8 C2 120.5(5) . . ? C19 C14 C15 118.8(5) . . ? C19 C14 C7 120.6(4) . . ? C15 C14 C7 120.6(5) . . ? C11 C10 C9 121.1(5) . . ? C10 C9 C8 119.8(5) . . ? C16 C15 C14 120.1(5) . . ? C15 C16 C17 120.5(5) . . ? C17 C18 C19 119.2(5) . . ? C13 C12 C11 120.4(5) . . ? C16 C17 C18 120.0(5) . . ? C10 C11 C12 119.2(5) . . ? _diffrn_measured_fraction_theta_max 26.3714 _diffrn_reflns_theta_full 26.3714 _diffrn_measured_fraction_theta_full 92.9000 _refine_diff_density_max 0.528 _refine_diff_density_min -0.467 _refine_diff_density_rms 0.110