Supplementary Material (ESI) for Perkin Transactions This journal is © The Royal Society of Chemistry 2001 data_global _journal_coden_Cambridge 188 _publ_contact_author_name 'Kevin J. Duffy' _publ_contact_author_address ; GlaxoSmithKline, 1250 South Collegeville Road, Collegeville, PA, 19426 USA ; _publ_contact_author_email 'KEVIN_J_DUFFY@SBPHRD.COM' _publ_requested_journal 'J. Chem. Soc., Perkin Trans. II' _publ_section_title. ; Pyrido[1,2-a]quinoxalines: Synthesis, Crystal Structure Determination and pH-Dependent Fluorescence. ; loop_ _publ_author_name _publ_author_address 'Kevin J. Duffy' ; GlaxoSmithKline, 1250 South Collegeville Road, Collegeville, PA 19426, USA. ; 'R. Curtius Haltiwanger' ; GlaxoSmithKline, 709 Swedeland Road, King of Prussia, PA 19406, USA. ; 'Alan J. Freyer' ; GlaxoSmithKline, 709 Swedeland Road, King of Prussia, PA 19406, USA. ; 'Florence Li' ; GlaxoSmithKline, 709 Swedeland Road, King of Prussia, PA 19406, USA. ; 'Juan I. Luengo' ; GlaxoSmithKline, 1250 South Collegeville Road, Collegeville, PA 19426, USA. ; 'H.Y. Cheng' ; GlaxoSmithKline, 709 Swedeland Road, King of Prussia, PA 19406, USA. ; data_Compound_3g _database_code_CSD 162091 _audit_creation_method SHELXL _chemical_name_systematic ; 8,10-Diphenyl-5,6-dihydro-6-oxo-2-trifluoromethylpyrido[1,2-a]quinoxalin-11-ium ; _chemical_name_common '3g; xray# x1668; SB-270031' _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C25 H15 F3 N2 O' _chemical_formula_weight 416.39 _chemical_melting_point 175 _chemical_compound_source ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'F' 'F' 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting 'Monoclinic' _symmetry_space_group_name_H-M 'P2(1)/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 7.045(3) _cell_length_b 10.615(4) _cell_length_c 25.694(10) _cell_angle_alpha 90.00 _cell_angle_beta 92.68(3) _cell_angle_gamma 90.00 _cell_volume 1919.3(13) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 20.1 _cell_measurement_theta_max 23.5 _exptl_crystal_description needle _exptl_crystal_colour red _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.441 _exptl_crystal_density_method ? _exptl_crystal_F_000 856 _exptl_absorpt_coefficient_mu 0.917 _exptl_absorpt_correction_type 'Semiempirical - psi scans - XPREP' _exptl_absorpt_correction_T_min 0.693 _exptl_absorpt_correction_T_max 0.906 _exptl_special_details ; ? ; _diffrn_refln_scan_speed_min 5.49 _diffrn_refln_scan_speed_max 1.18 _diffrn_refln_theta_min 3.44 _diffrn_refln_theta_max 119.96 _diffrn_standards_number 3 _diffrn_standards_interval_time 180 _diffrn_standards_decay_% 2.70 _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_monochromator 'vertically mounted graphite crystal' _diffrn_measurement_device 'serial diffractometer' _diffrn_radiation_source 'fine focus sealed tube' _diffrn_measurement_device_type 'Nonius Turbo CAD4' _diffrn_measurement_method '\w-2\q scans' _diffrn_reflns_number 3418 _diffrn_reflns_av_R_equivalents 0.0903 _diffrn_reflns_av_sigmaI/netI 0.0372 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 3.44 _diffrn_reflns_theta_max 59.94 _reflns_number_total 2843 _reflns_number_observed 2158 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'CAD4 (Enraf Nonius, 1977)' _computing_cell_refinement 'CAD4 (Enraf Nonius, 1977)' _computing_data_reduction 'XCAD4 (Siemens, 1990)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'XPW (Siemens, 1990)' _computing_publication_material 'CIFTAB (Sheldrick, 1993)' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 1 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.1376P)^2^+2.6419P] 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 riding _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0039(7) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2842 _refine_ls_number_parameters 308 _refine_ls_number_restraints 45 _refine_ls_R_factor_all 0.0936 _refine_ls_R_factor_obs 0.0602 _refine_ls_wR_factor_all 0.2412 _refine_ls_wR_factor_obs 0.1618 _refine_ls_goodness_of_fit_all 1.073 _refine_ls_goodness_of_fit_obs 0.840 _refine_ls_restrained_S_all 1.074 _refine_ls_restrained_S_obs 0.845 _refine_ls_shift/esd_max 0.007 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group F1A F -0.3762(6) -0.0981(16) -0.1892(3) 0.052(3) Uani 0.50 d PD . F2A F -0.1766(20) -0.1677(12) -0.2408(4) 0.121(8) Uani 0.50 d PD . F3A F -0.1819(19) 0.0261(9) -0.2211(5) 0.119(5) Uani 0.50 d PD . F1B F -0.2136(19) -0.1877(10) -0.2331(4) 0.089(4) Uani 0.50 d PD . F2B F -0.1464(20) 0.0068(11) -0.2310(5) 0.162(10) Uani 0.50 d PD . F3B F -0.3710(7) -0.0635(17) -0.1880(4) 0.085(6) Uani 0.50 d PD . N1 N 0.1993(4) 0.0677(3) -0.05155(12) 0.0334(8) Uani 1 d . . N5 N 0.2326(5) -0.1875(3) -0.01626(13) 0.0405(9) Uani 1 d . . O6 O 0.3316(5) -0.1097(3) 0.06269(11) 0.0502(9) Uani 1 d . . C1 C 0.0044(6) -0.0114(5) -0.1271(2) 0.0440(11) Uani 1 d . . H1A H -0.0295(6) 0.0704(5) -0.1366(2) 0.053 Uiso 1 calc R . C2 C -0.0613(6) -0.1125(4) -0.1567(2) 0.0464(11) Uani 1 d D . C3 C -0.0115(6) -0.2353(5) -0.1421(2) 0.0479(11) Uani 1 d . . H3A H -0.0495(6) -0.3027(5) -0.1632(2) 0.058 Uiso 1 calc R . C4 C 0.0924(6) -0.2563(4) -0.0971(2) 0.0442(11) Uani 1 d . . H4A H 0.1231(6) -0.3387(4) -0.0876(2) 0.053 Uiso 1 calc R . C6 C 0.2706(5) -0.0932(4) 0.0175(2) 0.0367(10) Uani 1 d . . C7 C 0.3037(5) 0.1355(4) 0.0334(2) 0.0350(9) Uani 1 d . . H7A H 0.3382(5) 0.1147(4) 0.0677(2) 0.042 Uiso 1 calc R . C8 C 0.3041(5) 0.2616(4) 0.0187(2) 0.0353(9) Uani 1 d . . C9 C 0.2686(6) 0.2830(4) -0.03445(15) 0.0374(10) Uani 1 d . . H9A H 0.2775(6) 0.3651(4) -0.04669(15) 0.045 Uiso 1 calc R . C10 C 0.2219(6) 0.1907(4) -0.0693(2) 0.0375(10) Uani 1 d . . C12 C 0.1222(5) -0.0334(4) -0.08281(15) 0.0367(10) Uani 1 d . . C13 C 0.1555(5) -0.1561(4) -0.06404(15) 0.0357(10) Uani 1 d . . C14 C 0.2543(5) 0.0407(4) -0.00080(14) 0.0323(9) Uani 1 d . . C15 C -0.1953(6) -0.0890(3) -0.2015(2) 0.0599(14) Uani 1 d D . C16 C 0.3487(5) 0.3633(4) 0.0562(2) 0.0364(10) Uani 1 d . . C17 C 0.4379(6) 0.3386(4) 0.1045(2) 0.0443(11) Uani 1 d . . H17A H 0.4772(6) 0.2569(4) 0.1125(2) 0.053 Uiso 1 calc R . C18 C 0.4690(7) 0.4323(4) 0.1407(2) 0.0513(12) Uani 1 d . . H18A H 0.5296(7) 0.4138(4) 0.1727(2) 0.062 Uiso 1 calc R . C19 C 0.4110(7) 0.5536(4) 0.1299(2) 0.0522(12) Uani 1 d . . H19A H 0.4289(7) 0.6165(4) 0.1548(2) 0.063 Uiso 1 calc R . C20 C 0.3268(7) 0.5814(4) 0.0822(2) 0.0509(12) Uani 1 d . . H20A H 0.2911(7) 0.6639(4) 0.0745(2) 0.061 Uiso 1 calc R . C21 C 0.2945(6) 0.4882(4) 0.0454(2) 0.0455(11) Uani 1 d . . H21A H 0.2362(6) 0.5083(4) 0.0133(2) 0.055 Uiso 1 calc R . C22 C 0.2187(6) 0.2195(4) -0.1260(2) 0.0380(10) Uani 1 d . . C23 C 0.1095(6) 0.3189(4) -0.1454(2) 0.0483(11) Uani 1 d . . H23A H 0.0340(6) 0.3641(4) -0.1232(2) 0.058 Uiso 1 calc R . C24 C 0.1122(7) 0.3514(5) -0.1974(2) 0.0571(13) Uani 1 d . . H24A H 0.0390(7) 0.4183(5) -0.2103(2) 0.069 Uiso 1 calc R . C25 C 0.2242(7) 0.2838(5) -0.2300(2) 0.0568(13) Uani 1 d . . H25A H 0.2240(7) 0.3041(5) -0.2652(2) 0.068 Uiso 1 calc R . C26 C 0.3364(7) 0.1866(5) -0.2109(2) 0.0497(12) Uani 1 d . . H26A H 0.4132(7) 0.1427(5) -0.2331(2) 0.060 Uiso 1 calc R . C27 C 0.3355(6) 0.1537(4) -0.1588(2) 0.0424(10) Uani 1 d . . H27A H 0.4119(6) 0.0884(4) -0.1458(2) 0.051 Uiso 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 F1A 0.031(4) 0.067(7) 0.058(6) -0.003(4) -0.005(3) 0.006(3) F2A 0.071(7) 0.246(20) 0.045(5) -0.050(7) -0.003(5) 0.046(9) F3A 0.148(10) 0.110(9) 0.091(8) 0.067(7) -0.076(7) -0.056(8) F1B 0.082(7) 0.101(7) 0.081(8) -0.061(6) -0.041(6) 0.028(5) F2B 0.190(15) 0.223(21) 0.068(7) 0.064(9) -0.049(8) -0.132(14) F3B 0.097(10) 0.090(11) 0.065(7) -0.021(5) -0.026(6) 0.040(6) N1 0.033(2) 0.032(2) 0.034(2) 0.0001(14) 0.0006(13) 0.0011(13) N5 0.044(2) 0.033(2) 0.044(2) -0.001(2) -0.003(2) 0.0016(15) O6 0.073(2) 0.035(2) 0.041(2) 0.0044(13) -0.0066(15) 0.0057(15) C1 0.040(2) 0.054(3) 0.038(2) -0.001(2) 0.002(2) -0.005(2) C2 0.038(2) 0.062(3) 0.038(2) -0.003(2) -0.001(2) -0.006(2) C3 0.042(2) 0.052(3) 0.050(3) -0.013(2) 0.004(2) -0.011(2) C4 0.039(2) 0.042(2) 0.051(3) -0.008(2) 0.003(2) -0.001(2) C6 0.038(2) 0.036(2) 0.036(2) 0.001(2) 0.000(2) 0.001(2) C7 0.036(2) 0.034(2) 0.035(2) -0.001(2) 0.001(2) 0.004(2) C8 0.034(2) 0.033(2) 0.039(2) 0.003(2) 0.003(2) 0.002(2) C9 0.042(2) 0.033(2) 0.038(2) 0.005(2) 0.008(2) 0.000(2) C10 0.035(2) 0.039(2) 0.038(2) 0.005(2) -0.002(2) 0.005(2) C12 0.033(2) 0.044(2) 0.033(2) -0.006(2) 0.001(2) 0.002(2) C13 0.031(2) 0.039(2) 0.037(2) -0.004(2) 0.005(2) 0.002(2) C14 0.030(2) 0.035(2) 0.032(2) 0.004(2) 0.005(2) -0.002(2) C15 0.055(3) 0.079(4) 0.044(3) -0.008(3) -0.007(2) -0.005(3) C16 0.039(2) 0.031(2) 0.040(2) 0.000(2) 0.005(2) -0.002(2) C17 0.052(3) 0.032(2) 0.049(3) -0.003(2) -0.001(2) 0.004(2) C18 0.056(3) 0.048(3) 0.049(3) -0.006(2) -0.002(2) -0.008(2) C19 0.060(3) 0.040(3) 0.058(3) -0.012(2) 0.018(2) -0.011(2) C20 0.064(3) 0.031(2) 0.059(3) 0.001(2) 0.017(2) -0.002(2) C21 0.057(3) 0.036(2) 0.045(2) 0.005(2) 0.011(2) -0.001(2) C22 0.042(2) 0.037(2) 0.035(2) 0.004(2) -0.002(2) -0.004(2) C23 0.049(3) 0.053(3) 0.043(2) 0.004(2) -0.004(2) 0.010(2) C24 0.062(3) 0.056(3) 0.051(3) 0.015(2) -0.014(2) 0.003(2) C25 0.063(3) 0.070(3) 0.037(2) 0.012(2) -0.002(2) -0.010(3) C26 0.056(3) 0.058(3) 0.035(2) 0.000(2) 0.004(2) -0.007(2) C27 0.046(2) 0.043(2) 0.038(2) 0.003(2) 0.006(2) -0.001(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 F1A C15 1.331(5) . yes F2A C15 1.322(5) . yes F3A C15 1.327(5) . yes F1B C15 1.329(5) . yes F2B C15 1.323(5) . yes F3B C15 1.328(5) . yes N1 C14 1.373(5) . yes N1 C10 1.395(5) . yes N1 C12 1.432(5) . yes N5 C6 1.342(5) . yes N5 C13 1.360(5) . yes O6 C6 1.233(5) . yes C1 C2 1.382(6) . yes C1 C12 1.396(6) . yes C1 H1A 0.93 . ? C2 C3 1.396(6) . yes C2 C15 1.476(6) . yes C3 C4 1.358(6) . yes C3 H3A 0.93 . ? C4 C13 1.419(6) . yes C4 H4A 0.93 . ? C6 C14 1.500(6) . yes C7 C14 1.370(5) . yes C7 C8 1.390(6) . yes C7 H7A 0.93 . ? C8 C9 1.397(6) . yes C8 C16 1.470(6) . yes C9 C10 1.357(6) . yes C9 H9A 0.93 . ? C10 C22 1.489(5) . yes C12 C13 1.405(6) . yes C16 C17 1.390(6) . yes C16 C21 1.404(6) . yes C17 C18 1.373(6) . yes C17 H17A 0.93 . ? C18 C19 1.375(7) . yes C18 H18A 0.93 . ? C19 C20 1.368(7) . yes C19 H19A 0.93 . ? C20 C21 1.379(6) . yes C20 H20A 0.93 . ? C21 H21A 0.93 . ? C22 C23 1.384(6) . yes C22 C27 1.391(6) . yes C23 C24 1.382(6) . yes C23 H23A 0.93 . ? C24 C25 1.379(7) . yes C24 H24A 0.93 . ? C25 C26 1.376(7) . yes C25 H25A 0.93 . ? C26 C27 1.385(6) . yes C26 H26A 0.93 . ? C27 H27A 0.93 . ? 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 C14 N1 C10 118.3(3) . . yes C14 N1 C12 117.4(3) . . yes C10 N1 C12 124.4(3) . . yes C6 N5 C13 117.3(3) . . yes C2 C1 C12 119.3(4) . . yes C2 C1 H1A 120.4(3) . . ? C12 C1 H1A 120.4(3) . . ? C1 C2 C3 120.3(4) . . yes C1 C2 C15 118.9(4) . . yes C3 C2 C15 120.7(3) . . yes C4 C3 C2 120.0(4) . . yes C4 C3 H3A 120.0(3) . . ? C2 C3 H3A 120.0(2) . . ? C3 C4 C13 121.8(4) . . yes C3 C4 H4A 119.1(3) . . ? C13 C4 H4A 119.1(3) . . ? O6 C6 N5 123.6(4) . . yes O6 C6 C14 116.6(3) . . yes N5 C6 C14 119.7(3) . . yes C14 C7 C8 122.4(4) . . yes C14 C7 H7A 118.8(2) . . ? C8 C7 H7A 118.8(2) . . ? C7 C8 C9 114.8(4) . . yes C7 C8 C16 122.2(4) . . yes C9 C8 C16 122.9(4) . . yes C10 C9 C8 123.7(4) . . yes C10 C9 H9A 118.2(2) . . ? C8 C9 H9A 118.2(2) . . ? C9 C10 N1 119.2(4) . . yes C9 C10 C22 119.3(4) . . yes N1 C10 C22 121.0(3) . . yes C1 C12 C13 121.2(4) . . yes C1 C12 N1 121.8(4) . . yes C13 C12 N1 116.7(3) . . yes N5 C13 C12 126.2(4) . . yes N5 C13 C4 117.2(4) . . yes C12 C13 C4 116.5(4) . . yes C7 C14 N1 120.6(4) . . yes C7 C14 C6 118.8(3) . . yes N1 C14 C6 120.6(3) . . yes F2A C15 F2B 90.6(14) . . yes F2A C15 F3A 106.3(5) . . yes F2B C15 F3A 18.2(15) . . yes F2A C15 F3B 117.0(12) . . yes F2B C15 F3B 105.2(5) . . yes F3A C15 F3B 89.7(13) . . yes F2A C15 F1B 17.2(14) . . yes F2B C15 F1B 106.0(5) . . yes F3A C15 F1B 120.0(12) . . yes F3B C15 F1B 104.8(5) . . yes F2A C15 F1A 105.4(5) . . yes F2B C15 F1A 118.0(12) . . yes F3A C15 F1A 104.0(5) . . yes F3B C15 F1A 16.0(14) . . yes F1B C15 F1A 91.2(12) . . yes F2A C15 C2 114.0(5) . . yes F2B C15 C2 113.7(5) . . yes F3A C15 C2 113.4(4) . . yes F3B C15 C2 113.7(5) . . yes F1B C15 C2 112.6(5) . . yes F1A C15 C2 112.8(5) . . yes C17 C16 C21 117.5(4) . . yes C17 C16 C8 121.3(4) . . yes C21 C16 C8 121.2(4) . . yes C18 C17 C16 121.3(4) . . yes C18 C17 H17A 119.4(3) . . ? C16 C17 H17A 119.4(2) . . ? C17 C18 C19 120.3(5) . . yes C17 C18 H18A 119.8(3) . . ? C19 C18 H18A 119.8(3) . . ? C20 C19 C18 119.7(4) . . yes C20 C19 H19A 120.2(3) . . ? C18 C19 H19A 120.2(3) . . ? C19 C20 C21 120.6(4) . . yes C19 C20 H20A 119.7(3) . . ? C21 C20 H20A 119.7(3) . . ? C20 C21 C16 120.6(4) . . yes C20 C21 H21A 119.7(3) . . ? C16 C21 H21A 119.7(3) . . ? C23 C22 C27 120.0(4) . . yes C23 C22 C10 119.4(4) . . yes C27 C22 C10 120.4(4) . . yes C24 C23 C22 120.3(4) . . yes C24 C23 H23A 119.8(3) . . ? C22 C23 H23A 119.8(3) . . ? C25 C24 C23 119.5(4) . . yes C25 C24 H24A 120.3(3) . . ? C23 C24 H24A 120.3(3) . . ? C26 C25 C24 120.6(4) . . yes C26 C25 H25A 119.7(3) . . ? C24 C25 H25A 119.7(3) . . ? C25 C26 C27 120.4(4) . . yes C25 C26 H26A 119.8(3) . . ? C27 C26 H26A 119.8(3) . . ? C26 C27 C22 119.2(4) . . yes C26 C27 H27A 120.4(3) . . ? C22 C27 H27A 120.4(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 C12 C1 C2 C3 0.6(6) . . . . yes C12 C1 C2 C15 176.2(3) . . . . yes C1 C2 C3 C4 3.9(6) . . . . yes C15 C2 C3 C4 -171.6(4) . . . . yes C2 C3 C4 C13 -0.8(7) . . . . yes C13 N5 C6 O6 176.3(4) . . . . yes C13 N5 C6 C14 -8.8(5) . . . . yes C14 C7 C8 C9 -6.0(5) . . . . yes C14 C7 C8 C16 177.1(4) . . . . yes C7 C8 C9 C10 5.1(6) . . . . yes C16 C8 C9 C10 -178.0(4) . . . . yes C8 C9 C10 N1 2.9(6) . . . . yes C8 C9 C10 C22 -169.8(4) . . . . yes C14 N1 C10 C9 -10.2(5) . . . . yes C12 N1 C10 C9 169.9(3) . . . . yes C14 N1 C10 C22 162.4(3) . . . . yes C12 N1 C10 C22 -17.6(6) . . . . yes C2 C1 C12 C13 -8.2(6) . . . . yes C2 C1 C12 N1 178.1(3) . . . . yes C14 N1 C12 C1 157.5(4) . . . . yes C10 N1 C12 C1 -22.6(6) . . . . yes C14 N1 C12 C13 -16.5(5) . . . . yes C10 N1 C12 C13 163.5(3) . . . . yes C6 N5 C13 C12 4.2(6) . . . . yes C6 N5 C13 C4 -171.9(3) . . . . yes C1 C12 C13 N5 -165.2(4) . . . . yes N1 C12 C13 N5 8.8(6) . . . . yes C1 C12 C13 C4 10.9(6) . . . . yes N1 C12 C13 C4 -175.0(3) . . . . yes C3 C4 C13 N5 170.1(4) . . . . yes C3 C4 C13 C12 -6.4(6) . . . . yes C8 C7 C14 N1 -1.2(6) . . . . yes C8 C7 C14 C6 175.9(3) . . . . yes C10 N1 C14 C7 9.4(5) . . . . yes C12 N1 C14 C7 -170.6(3) . . . . yes C10 N1 C14 C6 -167.6(3) . . . . yes C12 N1 C14 C6 12.4(5) . . . . yes O6 C6 C14 C7 -1.2(5) . . . . yes N5 C6 C14 C7 -176.5(4) . . . . yes O6 C6 C14 N1 175.8(3) . . . . yes N5 C6 C14 N1 0.6(5) . . . . yes C1 C2 C15 F2A 147.1(9) . . . . yes C3 C2 C15 F2A -37.3(10) . . . . yes C1 C2 C15 F2B 45.1(10) . . . . yes C3 C2 C15 F2B -139.3(10) . . . . yes C1 C2 C15 F3A 25.3(10) . . . . yes C3 C2 C15 F3A -159.1(9) . . . . yes C1 C2 C15 F3B -75.3(9) . . . . yes C3 C2 C15 F3B 100.3(9) . . . . yes C1 C2 C15 F1B 165.7(9) . . . . yes C3 C2 C15 F1B -18.6(9) . . . . yes C1 C2 C15 F1A -92.7(9) . . . . yes C3 C2 C15 F1A 82.9(9) . . . . yes C7 C8 C16 C17 16.3(6) . . . . yes C9 C8 C16 C17 -160.3(4) . . . . yes C7 C8 C16 C21 -160.5(4) . . . . yes C9 C8 C16 C21 22.9(6) . . . . yes C21 C16 C17 C18 1.0(6) . . . . yes C8 C16 C17 C18 -175.9(4) . . . . yes C16 C17 C18 C19 0.4(7) . . . . yes C17 C18 C19 C20 -1.9(7) . . . . yes C18 C19 C20 C21 2.0(7) . . . . yes C19 C20 C21 C16 -0.5(7) . . . . yes C17 C16 C21 C20 -1.0(6) . . . . yes C8 C16 C21 C20 176.0(4) . . . . yes C9 C10 C22 C23 -54.5(6) . . . . yes N1 C10 C22 C23 132.9(4) . . . . yes C9 C10 C22 C27 120.4(4) . . . . yes N1 C10 C22 C27 -52.1(5) . . . . yes C27 C22 C23 C24 1.6(7) . . . . yes C10 C22 C23 C24 176.6(4) . . . . yes C22 C23 C24 C25 0.1(7) . . . . yes C23 C24 C25 C26 -1.6(7) . . . . yes C24 C25 C26 C27 1.2(7) . . . . yes C25 C26 C27 C22 0.5(7) . . . . yes C23 C22 C27 C26 -1.9(6) . . . . yes C10 C22 C27 C26 -176.9(4) . . . . yes _refine_diff_density_max 0.385 _refine_diff_density_min -0.362 _refine_diff_density_rms 0.091 _cell_measurement_temperature 293 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 5.0 _cell_measurement_theta_max 25.0 _diffrn_attenuator_scale 11.96 _diffrn_orient_matrix_UB_11 0.016517 _diffrn_orient_matrix_UB_12 0.092994 _diffrn_orient_matrix_UB_13 -0.004050 _diffrn_orient_matrix_UB_21 -0.129489 _diffrn_orient_matrix_UB_22 0.014121 _diffrn_orient_matrix_UB_23 0.013269 _diffrn_orient_matrix_UB_31 0.056151 _diffrn_orient_matrix_UB_32 0.005241 _diffrn_orient_matrix_UB_33 0.036409 loop_ _diffrn_oricheck_refln_index_h _diffrn_oricheck_refln_index_k _diffrn_oricheck_refln_index_l 3 0 4 4 2 4 9 3 1 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 3 0 4 4 2 4 9 3 1 data_Compound_3i _database_code_CSD 162092 _audit_creation_method SHELXL _chemical_name_systematic ; 8,10-Diphenyl-2-nitro-5,6-dihydro-6-oxopyrido[1,2-a]quinoxalin-11-ium trifluoromethanesulfonate ; _chemical_name_common '3i; xray# x1679; SB-271995' _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C25 H18 F3 N3 O7 S' _chemical_formula_weight 561.48 _chemical_melting_point 222 _chemical_compound_source ? 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' _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 8.454(2) _cell_length_b 9.474(2) _cell_length_c 17.001(3) _cell_angle_alpha 74.91(3) _cell_angle_beta 85.33(3) _cell_angle_gamma 68.33(3) _cell_volume 1221.6(4) _cell_formula_units_Z 2 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plates _exptl_crystal_colour 'clear yellow' _exptl_crystal_size_max 1.20 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.526 _exptl_crystal_density_method ? _exptl_crystal_F_000 576 _exptl_absorpt_coefficient_mu 0.208 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_monochromator 'vertically mounted graphite crystal' _diffrn_measurement_device 'area detector \k goniostat' _diffrn_radiation_source 'rotating anode generator' _diffrn_measurement_device_type 'Nonius FAST' _diffrn_measurement_method 'thin slice \k scans' _diffrn_standards_number N/A _diffrn_standards_interval_count ? _diffrn_standards_interval_time N/A _diffrn_standards_decay_% ? _diffrn_reflns_number 13511 _diffrn_reflns_av_R_equivalents 0.1184 _diffrn_reflns_av_sigmaI/netI 0.0649 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.39 _diffrn_reflns_theta_max 22.96 _reflns_number_total 3303 _reflns_number_observed 2998 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'MADNES (Enraf Nonius, 1993)' _computing_cell_refinement 'MADNES (Enraf Nonius, 1993)' _computing_data_reduction 'PROCOR (Siemens, 1990)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'XPW (Siemens, 1995)' _computing_publication_material 'CIFTAB (Sheldrick, 1993)' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 2 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.1032P)^2^+1.2710P] 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 ? _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0654(80) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 3301 _refine_ls_number_parameters 392 _refine_ls_number_restraints 46 _refine_ls_R_factor_all 0.0763 _refine_ls_R_factor_obs 0.0705 _refine_ls_wR_factor_all 0.1850 _refine_ls_wR_factor_obs 0.1771 _refine_ls_goodness_of_fit_all 1.095 _refine_ls_goodness_of_fit_obs 1.108 _refine_ls_restrained_S_all 1.117 _refine_ls_restrained_S_obs 1.130 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group O4 O 0.7671(4) 0.6053(4) -0.0110(2) 0.0617(9) Uani 1 d . . O5 O 0.8521(5) 0.7623(4) 0.0310(2) 0.0656(10) Uani 1 d . . O6 O 1.1238(4) 0.1244(3) 0.46642(14) 0.0406(7) Uani 1 d . . N1 N 1.1252(3) 0.4586(3) 0.30707(15) 0.0232(6) Uani 1 d . . N3 N 0.8331(4) 0.6375(4) 0.0398(2) 0.0426(8) Uani 1 d . . N5 N 1.0496(4) 0.1874(3) 0.3340(2) 0.0301(7) Uani 1 d . . H5A H 1.0312(48) 0.0999(46) 0.3435(23) 0.033(10) Uiso 1 d . . C1 C 0.9739(4) 0.5498(4) 0.1732(2) 0.0296(8) Uani 1 d . . H1A H 0.9820(4) 0.6490(4) 0.1646(2) 0.036 Uiso 1 calc R . C2 C 0.8966(5) 0.5164(4) 0.1158(2) 0.0336(8) Uani 1 d . . C3 C 0.8783(5) 0.3736(4) 0.1266(2) 0.0390(9) Uani 1 d . . H3A H 0.8293(5) 0.3525(4) 0.0854(2) 0.047 Uiso 1 calc R . C4 C 0.9335(5) 0.2632(4) 0.1989(2) 0.0367(9) Uani 1 d . . H4A H 0.9191(5) 0.1664(4) 0.2081(2) 0.044 Uiso 1 calc R . C6 C 1.1010(4) 0.2161(4) 0.3991(2) 0.0295(8) Uani 1 d . . C7 C 1.1862(4) 0.3985(4) 0.4502(2) 0.0272(8) Uani 1 d . . H7A H 1.1928(4) 0.3310(4) 0.5023(2) 0.033 Uiso 1 calc R . C8 C 1.2288(4) 0.5301(4) 0.4412(2) 0.0246(7) Uani 1 d . . C9 C 1.2357(4) 0.6132(4) 0.3599(2) 0.0254(7) Uani 1 d . . H9A H 1.2725(4) 0.6985(4) 0.3501(2) 0.030 Uiso 1 calc R . C10 C 1.1914(4) 0.5756(4) 0.2946(2) 0.0243(7) Uani 1 d . . C12 C 1.0402(4) 0.4337(4) 0.2444(2) 0.0246(7) Uani 1 d . . C13 C 1.0113(4) 0.2939(4) 0.2594(2) 0.0274(8) Uani 1 d . . C14 C 1.1343(4) 0.3639(4) 0.3849(2) 0.0244(7) Uani 1 d . . C16 C 1.2767(4) 0.5734(4) 0.5108(2) 0.0262(8) Uani 1 d . . C17 C 1.3001(4) 0.4723(4) 0.5886(2) 0.0310(8) Uani 1 d . . H17A H 1.2839(4) 0.3766(4) 0.5969(2) 0.037 Uiso 1 calc R . C18 C 1.3472(4) 0.5119(4) 0.6539(2) 0.0354(9) Uani 1 d . . H18A H 1.3631(4) 0.4426(4) 0.7059(2) 0.042 Uiso 1 calc R . C19 C 1.3709(4) 0.6535(4) 0.6426(2) 0.0345(8) Uani 1 d . . H19A H 1.4017(4) 0.6807(4) 0.6869(2) 0.041 Uiso 1 calc R . C20 C 1.3486(4) 0.7543(4) 0.5655(2) 0.0340(8) Uani 1 d . . H20A H 1.3650(4) 0.8499(4) 0.5576(2) 0.041 Uiso 1 calc R . C21 C 1.3023(4) 0.7152(4) 0.4998(2) 0.0305(8) Uani 1 d . . H21A H 1.2880(4) 0.7842(4) 0.4477(2) 0.037 Uiso 1 calc R . C22 C 1.2347(5) 0.6496(4) 0.2111(2) 0.0311(8) Uani 1 d . . C23 C 1.1803(6) 0.8123(5) 0.1849(2) 0.0462(10) Uani 1 d . . H23A H 1.1128(6) 0.8751(5) 0.2188(2) 0.055 Uiso 1 calc R . C24 C 1.2259(8) 0.8807(6) 0.1093(3) 0.072(2) Uani 1 d . . H24A H 1.1870(8) 0.9905(6) 0.0908(3) 0.087 Uiso 1 calc R . C25 C 1.3281(9) 0.7888(8) 0.0609(3) 0.080(2) Uani 1 d . . H25A H 1.3603(9) 0.8364(8) 0.0097(3) 0.096 Uiso 1 calc R . C26 C 1.3843(7) 0.6272(7) 0.0866(3) 0.068(2) Uani 1 d . . H26A H 1.4549(7) 0.5654(7) 0.0531(3) 0.082 Uiso 1 calc R . C27 C 1.3364(5) 0.5560(5) 0.1621(2) 0.0417(10) Uani 1 d . . H27A H 1.3724(5) 0.4462(5) 0.1796(2) 0.050 Uiso 1 calc R . F1 F 0.4330(16) 0.0768(19) 0.1428(7) 0.207(13) Uani 0.50 d PD 1 F2 F 0.6460(18) -0.1465(9) 0.1842(8) 0.131(8) Uani 0.50 d PD 1 F3 F 0.6731(21) 0.0808(22) 0.1708(9) 0.157(10) Uani 0.50 d PD 1 F1' F 0.4541(12) 0.0879(12) 0.1344(5) 0.085(3) Uani 0.50 d PD 2 F2' F 0.6153(22) -0.1385(12) 0.1762(8) 0.144(8) Uani 0.50 d PD 2 F3' F 0.7001(15) 0.0511(19) 0.1785(9) 0.107(6) Uani 0.50 d PD 2 S1 S 0.49745(12) -0.00352(10) 0.29426(6) 0.0374(4) Uani 1 d D . O1 O 0.4275(4) 0.1583(4) 0.2946(2) 0.0670(10) Uani 1 d . . O2 O 0.6520(5) -0.0908(4) 0.3409(3) 0.0884(14) Uani 1 d . . O3 O 0.3793(4) -0.0825(3) 0.3042(2) 0.0494(8) Uani 1 d . . C28 C 0.5697(6) 0.0006(5) 0.1923(3) 0.074(2) Uani 1 d D . O99 O 0.9553(3) -0.0710(3) 0.3682(2) 0.0367(6) Uani 1 d D . H99A H 0.8513(61) -0.0610(63) 0.3442(34) 0.088(18) Uiso 1 d D . H99B H 0.9590(82) -0.1024(67) 0.4267(26) 0.096(19) Uiso 1 d 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 O4 0.074(2) 0.085(2) 0.031(2) -0.0066(15) -0.0138(15) -0.037(2) O5 0.102(3) 0.055(2) 0.037(2) 0.0075(14) -0.017(2) -0.036(2) O6 0.058(2) 0.0359(14) 0.0278(14) 0.0040(11) -0.0010(12) -0.0246(13) N1 0.0247(14) 0.0247(14) 0.0193(14) -0.0054(11) 0.0056(11) -0.0089(11) N3 0.046(2) 0.051(2) 0.028(2) -0.0045(15) 0.0025(15) -0.019(2) N5 0.033(2) 0.028(2) 0.032(2) -0.0048(13) 0.0037(13) -0.0160(13) C1 0.028(2) 0.033(2) 0.027(2) -0.0067(14) 0.0070(14) -0.0127(15) C2 0.031(2) 0.046(2) 0.022(2) -0.006(2) 0.0041(14) -0.014(2) C3 0.041(2) 0.053(2) 0.030(2) -0.014(2) 0.001(2) -0.022(2) C4 0.040(2) 0.039(2) 0.037(2) -0.013(2) 0.005(2) -0.020(2) C6 0.029(2) 0.031(2) 0.028(2) -0.004(2) 0.0041(14) -0.014(2) C7 0.027(2) 0.030(2) 0.021(2) -0.0052(14) 0.0064(14) -0.0085(15) C8 0.020(2) 0.028(2) 0.024(2) -0.0093(13) 0.0077(13) -0.0052(14) C9 0.027(2) 0.024(2) 0.025(2) -0.0091(13) 0.0068(13) -0.0089(14) C10 0.027(2) 0.023(2) 0.023(2) -0.0071(13) 0.0082(13) -0.0099(14) C12 0.021(2) 0.031(2) 0.021(2) -0.0082(13) 0.0065(13) -0.0096(14) C13 0.024(2) 0.031(2) 0.028(2) -0.0085(14) 0.0076(14) -0.0109(14) C14 0.023(2) 0.025(2) 0.021(2) -0.0050(13) 0.0054(13) -0.0064(14) C16 0.020(2) 0.031(2) 0.025(2) -0.0095(14) 0.0072(13) -0.0060(14) C17 0.028(2) 0.035(2) 0.029(2) -0.0085(15) 0.0054(15) -0.011(2) C18 0.033(2) 0.044(2) 0.023(2) -0.007(2) 0.0023(15) -0.008(2) C19 0.027(2) 0.046(2) 0.031(2) -0.016(2) 0.0000(15) -0.009(2) C20 0.030(2) 0.036(2) 0.039(2) -0.016(2) 0.002(2) -0.011(2) C21 0.029(2) 0.031(2) 0.029(2) -0.0081(14) 0.0023(15) -0.0079(15) C22 0.040(2) 0.042(2) 0.019(2) -0.0079(14) 0.0076(14) -0.025(2) C23 0.075(3) 0.044(2) 0.029(2) -0.003(2) 0.002(2) -0.036(2) C24 0.130(5) 0.072(3) 0.034(2) 0.009(2) -0.005(3) -0.072(3) C25 0.129(5) 0.124(5) 0.026(2) -0.009(3) 0.022(3) -0.100(4) C26 0.079(3) 0.124(5) 0.035(2) -0.038(3) 0.030(2) -0.068(3) C27 0.042(2) 0.062(2) 0.034(2) -0.023(2) 0.017(2) -0.029(2) F1 0.344(27) 0.298(23) 0.066(9) 0.063(10) -0.080(11) -0.268(22) F2 0.129(10) 0.092(7) 0.179(16) -0.100(9) 0.097(9) -0.022(6) F3 0.225(20) 0.270(21) 0.073(9) -0.045(10) 0.067(10) -0.210(18) F1' 0.109(6) 0.113(7) 0.039(5) 0.016(5) -0.010(5) -0.068(6) F2' 0.150(12) 0.264(21) 0.102(10) -0.119(12) 0.066(8) -0.131(13) F3' 0.072(5) 0.192(13) 0.102(11) -0.053(9) 0.044(6) -0.095(7) S1 0.0382(6) 0.0404(6) 0.0391(6) -0.0081(4) 0.0016(4) -0.0218(5) O1 0.064(2) 0.052(2) 0.105(3) -0.039(2) 0.022(2) -0.033(2) O2 0.077(3) 0.078(2) 0.103(3) 0.028(2) -0.050(2) -0.044(2) O3 0.055(2) 0.053(2) 0.055(2) -0.0145(13) 0.0107(14) -0.0387(15) C28 0.081(4) 0.104(5) 0.063(4) -0.033(3) 0.027(3) -0.059(4) O99 0.0393(15) 0.0369(14) 0.0358(15) -0.0086(11) 0.0050(12) -0.0173(12) _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 O4 N3 1.221(4) . yes O5 N3 1.221(4) . yes O6 C6 1.223(4) . yes N1 C10 1.379(4) . yes N1 C14 1.382(4) . yes N1 C12 1.445(4) . yes N3 C2 1.470(5) . yes N5 C6 1.346(4) . yes N5 C13 1.375(4) . yes N5 H5A 0.87(4) . ? C1 C2 1.378(5) . yes C1 C12 1.397(5) . yes C1 H1A 0.94 . ? C2 C3 1.381(5) . yes C3 C4 1.374(5) . yes C3 H3A 0.94 . ? C4 C13 1.408(5) . yes C4 H4A 0.94 . ? C6 C14 1.484(5) . yes C7 C14 1.381(5) . yes C7 C8 1.390(5) . yes C7 H7A 0.94 . ? C8 C9 1.409(5) . yes C8 C16 1.480(5) . yes C9 C10 1.369(5) . yes C9 H9A 0.94 . ? C10 C22 1.492(4) . yes C12 C13 1.390(5) . yes C16 C17 1.396(5) . yes C16 C21 1.401(5) . yes C17 C18 1.388(5) . yes C17 H17A 0.94 . ? C18 C19 1.392(5) . yes C18 H18A 0.94 . ? C19 C20 1.386(5) . yes C19 H19A 0.94 . ? C20 C21 1.390(5) . yes C20 H20A 0.94 . ? C21 H21A 0.94 . ? C22 C27 1.387(5) . yes C22 C23 1.393(5) . yes C23 C24 1.375(6) . yes C23 H23A 0.94 . ? C24 C25 1.372(8) . yes C24 H24A 0.94 . ? C25 C26 1.382(8) . yes C25 H25A 0.94 . ? C26 C27 1.389(6) . yes C26 H26A 0.94 . ? C27 H27A 0.94 . ? F1 C28 1.338(7) . yes F2 C28 1.341(6) . yes F3 C28 1.330(7) . yes F1' C28 1.321(6) . yes F2' C28 1.325(7) . yes F3' C28 1.337(6) . yes S1 O1 1.426(3) . yes S1 O3 1.430(3) . yes S1 O2 1.432(3) . yes S1 C28 1.786(5) . yes O99 H99A 0.96(4) . ? O99 H99B 0.96(4) . ? 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 C10 N1 C14 118.1(3) . . yes C10 N1 C12 123.9(2) . . yes C14 N1 C12 118.0(3) . . yes O5 N3 O4 124.4(3) . . yes O5 N3 C2 118.1(3) . . yes O4 N3 C2 117.6(3) . . yes C6 N5 C13 123.2(3) . . yes C6 N5 H5A 115.1(25) . . ? C13 N5 H5A 121.3(25) . . ? C2 C1 C12 118.9(3) . . yes C2 C1 H1A 120.6(2) . . ? C12 C1 H1A 120.6(2) . . ? C1 C2 C3 122.6(3) . . yes C1 C2 N3 118.3(3) . . yes C3 C2 N3 119.0(3) . . yes C4 C3 C2 118.4(3) . . yes C4 C3 H3A 120.8(2) . . ? C2 C3 H3A 120.8(2) . . ? C3 C4 C13 120.4(3) . . yes C3 C4 H4A 119.8(2) . . ? C13 C4 H4A 119.8(2) . . ? O6 C6 N5 122.4(3) . . yes O6 C6 C14 121.0(3) . . yes N5 C6 C14 116.6(3) . . yes C14 C7 C8 122.0(3) . . yes C14 C7 H7A 119.0(2) . . ? C8 C7 H7A 119.0(2) . . ? C7 C8 C9 115.0(3) . . yes C7 C8 C16 122.8(3) . . yes C9 C8 C16 122.1(3) . . yes C10 C9 C8 123.0(3) . . yes C10 C9 H9A 118.5(2) . . ? C8 C9 H9A 118.5(2) . . ? C9 C10 N1 119.9(3) . . yes C9 C10 C22 118.8(3) . . yes N1 C10 C22 121.0(3) . . yes C13 C12 C1 119.3(3) . . yes C13 C12 N1 118.2(3) . . yes C1 C12 N1 122.3(3) . . yes N5 C13 C12 121.2(3) . . yes N5 C13 C4 118.8(3) . . yes C12 C13 C4 119.9(3) . . yes C7 C14 N1 120.9(3) . . yes C7 C14 C6 118.5(3) . . yes N1 C14 C6 120.5(3) . . yes C17 C16 C21 118.7(3) . . yes C17 C16 C8 120.5(3) . . yes C21 C16 C8 120.7(3) . . yes C18 C17 C16 120.6(3) . . yes C18 C17 H17A 119.7(2) . . ? C16 C17 H17A 119.7(2) . . ? C17 C18 C19 120.3(3) . . yes C17 C18 H18A 119.9(2) . . ? C19 C18 H18A 119.9(2) . . ? C20 C19 C18 119.5(3) . . yes C20 C19 H19A 120.3(2) . . ? C18 C19 H19A 120.3(2) . . ? C19 C20 C21 120.5(3) . . yes C19 C20 H20A 119.7(2) . . ? C21 C20 H20A 119.7(2) . . ? C20 C21 C16 120.3(3) . . yes C20 C21 H21A 119.9(2) . . ? C16 C21 H21A 119.9(2) . . ? C27 C22 C23 120.6(3) . . yes C27 C22 C10 119.8(3) . . yes C23 C22 C10 119.4(3) . . yes C24 C23 C22 119.6(4) . . yes C24 C23 H23A 120.2(3) . . ? C22 C23 H23A 120.2(2) . . ? C25 C24 C23 120.1(5) . . yes C25 C24 H24A 119.9(3) . . ? C23 C24 H24A 119.9(3) . . ? C24 C25 C26 120.8(4) . . yes C24 C25 H25A 119.6(3) . . ? C26 C25 H25A 119.6(3) . . ? C25 C26 C27 119.9(4) . . yes C25 C26 H26A 120.0(3) . . ? C27 C26 H26A 120.0(3) . . ? C22 C27 C26 119.0(4) . . yes C22 C27 H27A 120.5(2) . . ? C26 C27 H27A 120.5(3) . . ? O1 S1 O3 116.2(2) . . yes O1 S1 O2 114.2(2) . . yes O3 S1 O2 114.4(2) . . yes O1 S1 C28 103.2(2) . . yes O3 S1 C28 104.2(2) . . yes O2 S1 C28 102.2(3) . . yes F1' C28 F2' 101.0(10) . . yes F1' C28 F3' 107.4(8) . . yes F2' C28 F3' 109.6(8) . . yes F3 C28 F1 106.5(9) . . yes F3 C28 F2 110.9(8) . . yes F1 C28 F2 110.3(10) . . yes F1' C28 S1 115.6(6) . . yes F2' C28 S1 112.1(6) . . yes F3 C28 S1 112.1(7) . . yes F3' C28 S1 110.5(7) . . yes F1 C28 S1 107.4(7) . . yes F2 C28 S1 109.6(6) . . yes H99A O99 H99B 114.2(51) . . ? 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 C12 C1 C2 C3 1.5(5) . . . . yes C12 C1 C2 N3 -177.8(3) . . . . yes O5 N3 C2 C1 0.1(5) . . . . yes O4 N3 C2 C1 178.9(3) . . . . yes O5 N3 C2 C3 -179.2(4) . . . . yes O4 N3 C2 C3 -0.4(5) . . . . yes C1 C2 C3 C4 2.7(6) . . . . yes N3 C2 C3 C4 -178.0(3) . . . . yes C2 C3 C4 C13 -1.9(5) . . . . yes C13 N5 C6 O6 175.1(3) . . . . yes C13 N5 C6 C14 -6.8(5) . . . . yes C14 C7 C8 C9 -7.6(5) . . . . yes C14 C7 C8 C16 177.0(3) . . . . yes C7 C8 C9 C10 4.8(5) . . . . yes C16 C8 C9 C10 -179.8(3) . . . . yes C8 C9 C10 N1 4.8(5) . . . . yes C8 C9 C10 C22 -168.2(3) . . . . yes C14 N1 C10 C9 -11.6(4) . . . . yes C12 N1 C10 C9 165.6(3) . . . . yes C14 N1 C10 C22 161.3(3) . . . . yes C12 N1 C10 C22 -21.6(5) . . . . yes C2 C1 C12 C13 -6.5(5) . . . . yes C2 C1 C12 N1 179.1(3) . . . . yes C10 N1 C12 C13 166.6(3) . . . . yes C14 N1 C12 C13 -16.2(4) . . . . yes C10 N1 C12 C1 -19.0(4) . . . . yes C14 N1 C12 C1 158.2(3) . . . . yes C6 N5 C13 C12 6.6(5) . . . . yes C6 N5 C13 C4 -170.1(3) . . . . yes C1 C12 C13 N5 -169.4(3) . . . . yes N1 C12 C13 N5 5.3(5) . . . . yes C1 C12 C13 C4 7.3(5) . . . . yes N1 C12 C13 C4 -178.1(3) . . . . yes C3 C4 C13 N5 173.6(3) . . . . yes C3 C4 C13 C12 -3.1(5) . . . . yes C8 C7 C14 N1 1.0(5) . . . . yes C8 C7 C14 C6 176.5(3) . . . . yes C10 N1 C14 C7 8.9(4) . . . . yes C12 N1 C14 C7 -168.4(3) . . . . yes C10 N1 C14 C6 -166.5(3) . . . . yes C12 N1 C14 C6 16.2(4) . . . . yes O6 C6 C14 C7 -2.2(5) . . . . yes N5 C6 C14 C7 179.6(3) . . . . yes O6 C6 C14 N1 173.3(3) . . . . yes N5 C6 C14 N1 -4.9(5) . . . . yes C7 C8 C16 C17 7.5(5) . . . . yes C9 C8 C16 C17 -167.6(3) . . . . yes C7 C8 C16 C21 -173.6(3) . . . . yes C9 C8 C16 C21 11.3(5) . . . . yes C21 C16 C17 C18 0.3(5) . . . . yes C8 C16 C17 C18 179.2(3) . . . . yes C16 C17 C18 C19 0.3(5) . . . . yes C17 C18 C19 C20 -0.6(5) . . . . yes C18 C19 C20 C21 0.3(5) . . . . yes C19 C20 C21 C16 0.3(5) . . . . yes C17 C16 C21 C20 -0.6(5) . . . . yes C8 C16 C21 C20 -179.5(3) . . . . yes C9 C10 C22 C27 121.5(4) . . . . yes N1 C10 C22 C27 -51.4(5) . . . . yes C9 C10 C22 C23 -54.8(5) . . . . yes N1 C10 C22 C23 132.3(3) . . . . yes C27 C22 C23 C24 1.0(6) . . . . yes C10 C22 C23 C24 177.3(4) . . . . yes C22 C23 C24 C25 -1.7(7) . . . . yes C23 C24 C25 C26 1.0(8) . . . . yes C24 C25 C26 C27 0.4(8) . . . . yes C23 C22 C27 C26 0.5(6) . . . . yes C10 C22 C27 C26 -175.9(4) . . . . yes C25 C26 C27 C22 -1.1(7) . . . . yes O1 S1 C28 F1' -55.0(7) . . . . yes O3 S1 C28 F1' 66.8(7) . . . . yes O2 S1 C28 F1' -173.8(7) . . . . yes O1 S1 C28 F2' -170.1(9) . . . . yes O3 S1 C28 F2' -48.3(9) . . . . yes O2 S1 C28 F2' 71.1(9) . . . . yes O1 S1 C28 F3 53.8(10) . . . . yes O3 S1 C28 F3 175.6(10) . . . . yes O2 S1 C28 F3 -65.0(10) . . . . yes O1 S1 C28 F3' 67.3(8) . . . . yes O3 S1 C28 F3' -170.9(8) . . . . yes O2 S1 C28 F3' -51.5(8) . . . . yes O1 S1 C28 F1 -62.9(8) . . . . yes O3 S1 C28 F1 58.9(8) . . . . yes O2 S1 C28 F1 178.3(8) . . . . yes O1 S1 C28 F2 177.4(7) . . . . yes O3 S1 C28 F2 -60.8(8) . . . . yes O2 S1 C28 F2 58.6(8) . . . . yes _refine_diff_density_max 0.430 _refine_diff_density_min -0.400 _refine_diff_density_rms 0.093 _exptl_crystal_description 'plates' _exptl_crystal_colour 'clear yellow' _computing_data_collection 'MADNES (Enraf Nonius, 1993)' _computing_cell_refinement 'MADNES (Enraf Nonius, 1993)' _computing_data_reduction 'PROCOR (Siemens, 1990)' _computing_data_merging 'XPREP (Siemens, 1995)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_solution 'DIRDIF (Beurskens, 1990)' _computing_structure_refinement 'SHELXL (Sheldrick, 1993)' _computing_molecular_graphics 'XPW (Siemens, 1995)' _computing_publication_material 'CIFTAB (Sheldrick, 1993)' data_Compound_3k _database_code_CSD 162093 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4-Hydroxy-8,10-diphenyl-5,6-dihydro-6-oxopyrido[1,2-a]quinoxalin-11-ium trifluoromethanesulfonate ; _exptl_crystal_description 'prisms' _exptl_crystal_colour 'clear colorless' _chemical_name_common '3k; xray# x1737; SB-271225' _chemical_melting_point '272-273' _chemical_formula_moiety ? _chemical_formula_sum 'C26 H21 F3 N2 O6 S' _chemical_formula_weight 546.51 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' _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 7.633(3) _cell_length_b 10.495(4) _cell_length_c 15.251(6) _cell_angle_alpha 98.61(3) _cell_angle_beta 90.52(3) _cell_angle_gamma 93.99(3) _cell_volume 1204.8(8) _cell_formula_units_Z 2 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 13.00 _cell_measurement_theta_max 14.85 _exptl_crystal_size_max 0.58 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.506 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 564 _exptl_absorpt_coefficient_mu 0.205 _exptl_absorpt_correction_type 'Semiempirical - psi scans - XPREP' _exptl_absorpt_correction_T_min 0.8905 _exptl_absorpt_correction_T_max 0.9564 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_refln_scan_speed_min 1.5 _diffrn_refln_scan_speed_max 5.49 _diffrn_ambient_temperature 223(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'vertically mounted graphite crystal' _diffrn_measurement_device 'serial diffractometer' _diffrn_measurement_device_type 'Nonius Turbo CAD4' _diffrn_measurement_method '\w-2\q scans' _diffrn_standards_number 3 _diffrn_standards_interval_time 180 _diffrn_standards_decay_% 0.0 _diffrn_reflns_number 9167 _diffrn_reflns_av_R_equivalents 0.0176 _diffrn_reflns_av_sigmaI/netI 0.0200 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.35 _diffrn_reflns_theta_max 24.99 _reflns_number_total 4216 _reflns_number_gt 3587 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CAD4 (Enraf Nonius, 1977)' _computing_cell_refinement 'CAD4 (Enraf Nonius, 1977)' _computing_data_reduction 'XCAD4 (Siemens, 1990)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'XPW (Siemens, 1990)' _computing_publication_material 'CIFTAB (Sheldrick, 1993)' _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^)+(0.1486P)^2^+0.1165P] 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 4216 _refine_ls_number_parameters 360 _refine_ls_number_restraints 5 _refine_ls_R_factor_all 0.0886 _refine_ls_R_factor_gt 0.0815 _refine_ls_wR_factor_ref 0.2050 _refine_ls_wR_factor_gt 0.1943 _refine_ls_goodness_of_fit_ref 1.157 _refine_ls_restrained_S_all 1.166 _refine_ls_shift/su_max 0.093 _refine_ls_shift/su_mean 0.012 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 0.0865(3) 0.77752(19) 0.31756(13) 0.0477(5) Uani 1 1 d . . . N5 N -0.0494(3) 0.5684(2) 0.39169(14) 0.0509(5) Uani 1 1 d D . . H5N H -0.078(4) 0.4931(15) 0.4057(19) 0.058(8) Uiso 1 1 d D . . O4 O -0.2927(3) 0.39560(18) 0.30510(13) 0.0606(5) Uani 1 1 d D . . H4O H -0.385(3) 0.366(4) 0.278(3) 0.098(13) Uiso 1 1 d D . . O6 O 0.0659(3) 0.66179(18) 0.52582(12) 0.0627(5) Uani 1 1 d . . . C1 C -0.1156(3) 0.7105(3) 0.18840(16) 0.0536(6) Uani 1 1 d . . . H1B H -0.0781 0.7844 0.1637 0.064 Uiso 1 1 calc R . . C2 C -0.2456(4) 0.6229(3) 0.14660(17) 0.0580(6) Uani 1 1 d . . . H2A H -0.2956 0.6377 0.0928 0.070 Uiso 1 1 calc R . . C3 C -0.3028(4) 0.5149(3) 0.18210(17) 0.0570(6) Uani 1 1 d . . . H3A H -0.3881 0.4552 0.1515 0.068 Uiso 1 1 calc R . . C4 C -0.2356(3) 0.4936(2) 0.26262(17) 0.0520(6) Uani 1 1 d . . . C6 C 0.0319(3) 0.6659(2) 0.44766(16) 0.0513(6) Uani 1 1 d . . . C7 C 0.1750(3) 0.8879(2) 0.46221(16) 0.0508(6) Uani 1 1 d . . . H7A H 0.1769 0.8894 0.5240 0.061 Uiso 1 1 calc R . . C8 C 0.2541(3) 0.9925(2) 0.42667(16) 0.0493(6) Uani 1 1 d . . . C9 C 0.2658(3) 0.9741(2) 0.33465(17) 0.0511(6) Uani 1 1 d . . . H9A H 0.3287 1.0380 0.3081 0.061 Uiso 1 1 calc R . . C10 C 0.1898(3) 0.8670(2) 0.28019(16) 0.0489(5) Uani 1 1 d . . . C12 C -0.0419(3) 0.6868(2) 0.26775(16) 0.0477(5) Uani 1 1 d . . . C13 C -0.1046(3) 0.5817(2) 0.30667(16) 0.0488(5) Uani 1 1 d . . . C14 C 0.0947(3) 0.7832(2) 0.40860(16) 0.0490(6) Uani 1 1 d . . . C16 C 0.3345(3) 1.1105(2) 0.48281(16) 0.0503(6) Uani 1 1 d . . . C17 C 0.3340(3) 1.1234(2) 0.57519(17) 0.0533(6) Uani 1 1 d . . . H17A H 0.2787 1.0577 0.6030 0.064 Uiso 1 1 calc R . . C18 C 0.4144(4) 1.2323(3) 0.62625(18) 0.0568(6) Uani 1 1 d . . . H18A H 0.4136 1.2395 0.6884 0.068 Uiso 1 1 calc R . . C19 C 0.4956(4) 1.3304(2) 0.58701(19) 0.0586(6) Uani 1 1 d . . . H19A H 0.5505 1.4039 0.6220 0.070 Uiso 1 1 calc R . . C20 C 0.4950(4) 1.3193(3) 0.4959(2) 0.0639(7) Uani 1 1 d . . . H20A H 0.5492 1.3861 0.4687 0.077 Uiso 1 1 calc R . . C21 C 0.4155(4) 1.2109(3) 0.44398(19) 0.0610(7) Uani 1 1 d . . . H21A H 0.4162 1.2048 0.3819 0.073 Uiso 1 1 calc R . . C22 C 0.2326(3) 0.8439(2) 0.18473(16) 0.0506(6) Uani 1 1 d . . . C23 C 0.2349(4) 0.9459(3) 0.13571(18) 0.0606(7) Uani 1 1 d . . . H23A H 0.2014 1.0273 0.1617 0.073 Uiso 1 1 calc R . . C24 C 0.2871(5) 0.9260(3) 0.0482(2) 0.0701(8) Uani 1 1 d . . . H24A H 0.2897 0.9947 0.0150 0.084 Uiso 1 1 calc R . . C25 C 0.3356(5) 0.8065(3) 0.00919(19) 0.0700(8) Uani 1 1 d . . . H25A H 0.3695 0.7938 -0.0504 0.084 Uiso 1 1 calc R . . C26 C 0.3339(4) 0.7057(3) 0.05806(18) 0.0607(7) Uani 1 1 d . . . H26A H 0.3676 0.6245 0.0318 0.073 Uiso 1 1 calc R . . C27 C 0.2830(3) 0.7240(2) 0.14501(17) 0.0540(6) Uani 1 1 d . . . H27A H 0.2823 0.6551 0.1779 0.065 Uiso 1 1 calc R . . S1 S -0.75686(8) 0.33182(6) 0.22777(4) 0.0551(3) Uani 1 1 d . . . C30 C -0.8159(4) 0.3325(3) 0.11117(19) 0.0609(7) Uani 1 1 d . . . F1 F -0.9535(3) 0.3988(2) 0.10315(14) 0.0912(6) Uani 1 1 d . . . F2 F -0.6837(3) 0.3892(2) 0.07128(12) 0.0873(6) Uani 1 1 d . . . F3 F -0.8480(3) 0.21556(18) 0.06695(14) 0.0935(7) Uani 1 1 d . . . O1 O -0.9018(3) 0.2596(3) 0.25922(17) 0.0875(7) Uani 1 1 d . . . O2 O -0.7347(3) 0.4658(2) 0.26340(13) 0.0679(5) Uani 1 1 d . . . O3 O -0.5960(3) 0.26643(18) 0.22182(13) 0.0623(5) Uani 1 1 d . . . O98 O -1.1282(8) 0.0444(8) 0.2856(5) 0.091(2) Uani 0.50 1 d PD A 1 H98O H -1.0575 0.1116 0.2774 0.109 Uiso 0.50 1 d PRD A 1 O99 O -1.1898(13) 0.0951(9) 0.3073(4) 0.118(3) Uani 0.50 1 d PD A 2 H99O H -1.1000 0.1468 0.2924 0.141 Uiso 0.50 1 d PRD A 2 C99 C -1.2549(6) 0.0536(4) 0.2226(3) 0.0976(12) Uani 1 1 d D . . H99A H -1.3447 -0.0150 0.2230 0.146 Uiso 0.50 1 d PR A 1 H99B H -1.3057 0.1353 0.2357 0.146 Uiso 0.50 1 d PR A 1 H99C H -1.2029 0.0465 0.1652 0.146 Uiso 0.50 1 d PR A 1 H99D H -1.3563 -0.0052 0.2249 0.146 Uiso 0.50 1 d PR A 2 H99E H -1.2876 0.1269 0.1970 0.146 Uiso 0.50 1 d PR A 2 H99F H -1.1672 0.0107 0.1870 0.146 Uiso 0.50 1 d PR A 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0494(11) 0.0485(10) 0.0458(10) 0.0095(8) 0.0003(8) 0.0031(8) N5 0.0560(12) 0.0480(11) 0.0497(11) 0.0130(9) -0.0010(9) -0.0024(9) O4 0.0611(11) 0.0595(11) 0.0603(11) 0.0128(8) -0.0054(9) -0.0078(9) O6 0.0802(13) 0.0596(11) 0.0483(10) 0.0160(8) -0.0079(9) -0.0115(9) C1 0.0534(14) 0.0596(14) 0.0490(13) 0.0118(11) 0.0009(10) 0.0035(11) C2 0.0569(14) 0.0699(16) 0.0473(13) 0.0105(11) -0.0024(11) 0.0019(12) C3 0.0532(14) 0.0629(15) 0.0517(13) 0.0028(11) -0.0008(10) -0.0048(11) C4 0.0510(13) 0.0516(13) 0.0522(13) 0.0059(10) 0.0042(10) -0.0004(10) C6 0.0519(13) 0.0535(13) 0.0491(13) 0.0115(10) -0.0002(10) 0.0003(10) C7 0.0529(13) 0.0551(13) 0.0448(12) 0.0098(10) -0.0010(10) 0.0031(10) C8 0.0482(13) 0.0481(12) 0.0516(13) 0.0075(10) 0.0013(10) 0.0048(10) C9 0.0536(13) 0.0484(12) 0.0519(13) 0.0105(10) 0.0029(10) 0.0011(10) C10 0.0514(13) 0.0479(12) 0.0486(12) 0.0107(10) 0.0019(10) 0.0042(10) C12 0.0456(12) 0.0497(12) 0.0471(12) 0.0053(9) 0.0013(9) 0.0018(9) C13 0.0483(12) 0.0528(13) 0.0457(12) 0.0071(10) 0.0025(9) 0.0062(10) C14 0.0501(13) 0.0515(13) 0.0464(12) 0.0107(10) 0.0013(10) 0.0031(10) C16 0.0499(13) 0.0491(13) 0.0517(13) 0.0066(10) 0.0002(10) 0.0049(10) C17 0.0548(14) 0.0525(13) 0.0520(14) 0.0065(11) 0.0047(11) 0.0032(11) C18 0.0564(14) 0.0608(15) 0.0511(13) 0.0003(11) 0.0018(11) 0.0077(11) C19 0.0578(15) 0.0501(14) 0.0642(16) -0.0027(11) -0.0004(12) 0.0016(11) C20 0.0742(18) 0.0524(14) 0.0634(16) 0.0079(12) 0.0031(13) -0.0057(12) C21 0.0756(18) 0.0540(14) 0.0523(14) 0.0076(11) 0.0004(12) -0.0025(12) C22 0.0496(13) 0.0529(13) 0.0490(13) 0.0090(10) 0.0008(10) -0.0016(10) C23 0.0781(18) 0.0505(13) 0.0537(14) 0.0103(11) 0.0077(13) 0.0021(12) C24 0.098(2) 0.0593(15) 0.0562(15) 0.0173(12) 0.0111(14) 0.0055(14) C25 0.087(2) 0.0738(18) 0.0501(14) 0.0103(13) 0.0135(13) 0.0069(15) C26 0.0675(16) 0.0571(15) 0.0570(15) 0.0052(11) 0.0071(12) 0.0078(12) C27 0.0580(14) 0.0495(13) 0.0550(14) 0.0093(10) 0.0011(11) 0.0034(10) S1 0.0545(4) 0.0574(4) 0.0536(4) 0.0108(3) -0.0013(3) -0.0009(3) C30 0.0649(16) 0.0596(15) 0.0576(15) 0.0053(12) -0.0065(12) 0.0084(12) F1 0.0872(13) 0.1081(15) 0.0807(12) 0.0086(11) -0.0159(10) 0.0394(11) F2 0.0916(14) 0.1125(16) 0.0602(10) 0.0257(10) 0.0021(9) -0.0034(11) F3 0.1274(18) 0.0674(11) 0.0800(12) -0.0052(9) -0.0360(12) 0.0059(11) O1 0.0715(14) 0.1095(19) 0.0836(16) 0.0322(13) 0.0042(12) -0.0171(13) O2 0.0753(13) 0.0665(12) 0.0600(11) 0.0023(9) -0.0040(9) 0.0087(10) O3 0.0626(11) 0.0574(10) 0.0668(11) 0.0100(8) -0.0099(9) 0.0040(8) O98 0.069(3) 0.086(5) 0.128(5) 0.059(4) 0.002(3) -0.002(3) O99 0.148(8) 0.108(7) 0.099(5) 0.047(4) -0.013(5) -0.046(5) C99 0.088(3) 0.089(3) 0.120(3) 0.024(2) 0.003(2) 0.012(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 N1 C10 1.376(3) . yes N1 C14 1.381(3) . yes N1 C12 1.444(3) . yes N5 C6 1.342(3) . yes N5 C13 1.389(3) . yes N5 H5N 0.863(10) . ? O4 C4 1.345(3) . yes O4 H4O 0.835(10) . ? O6 C6 1.225(3) . yes C1 C2 1.386(4) . yes C1 C12 1.393(4) . yes C1 H1B 0.9400 . ? C2 C3 1.374(4) . yes C2 H2A 0.9400 . ? C3 C4 1.381(4) . yes C3 H3A 0.9400 . ? C4 C13 1.407(4) . yes C6 C14 1.497(3) . yes C7 C14 1.371(4) . yes C7 C8 1.398(4) . yes C7 H7A 0.9400 . ? C8 C9 1.392(4) . yes C8 C16 1.487(4) . yes C9 C10 1.382(4) . yes C9 H9A 0.9400 . ? C10 C22 1.483(3) . yes C12 C13 1.387(4) . yes C16 C21 1.395(4) . yes C16 C17 1.395(4) . yes C17 C18 1.384(4) . yes C17 H17A 0.9400 . ? C18 C19 1.381(4) . yes C18 H18A 0.9400 . ? C19 C20 1.377(4) . yes C19 H19A 0.9400 . ? C20 C21 1.384(4) . yes C20 H20A 0.9400 . ? C21 H21A 0.9400 . ? C22 C27 1.393(4) . yes C22 C23 1.394(4) . yes C23 C24 1.386(4) . yes C23 H23A 0.9400 . ? C24 C25 1.382(4) . yes C24 H24A 0.9400 . ? C25 C26 1.381(4) . yes C25 H25A 0.9400 . ? C26 C27 1.375(4) . yes C26 H26A 0.9400 . ? C27 H27A 0.9400 . ? S1 O1 1.425(2) . yes S1 O2 1.428(2) . yes S1 O3 1.445(2) . yes S1 C30 1.832(3) . yes C30 F1 1.314(3) . yes C30 F3 1.315(3) . yes C30 F2 1.333(4) . yes O98 C99 1.375(6) . yes O98 H98O 0.8827 . ? O98 H99O 1.0709 . ? O99 C99 1.376(6) . yes O99 H98O 1.1249 . ? O99 H99O 0.8971 . ? C99 H99A 0.9600 . ? C99 H99B 0.9600 . ? C99 H99C 0.9600 . ? C99 H99D 0.9600 . ? C99 H99E 0.9600 . ? C99 H99F 0.9600 . ? 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 C10 N1 C14 118.1(2) . . yes C10 N1 C12 123.3(2) . . yes C14 N1 C12 118.3(2) . . yes C6 N5 C13 122.7(2) . . yes C6 N5 H5N 124(2) . . ? C13 N5 H5N 113(2) . . ? C4 O4 H4O 104(3) . . ? C2 C1 C12 118.7(2) . . yes C2 C1 H1B 120.7 . . ? C12 C1 H1B 120.7 . . ? C3 C2 C1 121.4(2) . . yes C3 C2 H2A 119.3 . . ? C1 C2 H2A 119.3 . . ? C2 C3 C4 120.2(2) . . yes C2 C3 H3A 119.9 . . ? C4 C3 H3A 119.9 . . ? O4 C4 C3 124.2(2) . . yes O4 C4 C13 116.4(2) . . yes C3 C4 C13 119.3(2) . . yes O6 C6 N5 124.5(2) . . yes O6 C6 C14 118.9(2) . . yes N5 C6 C14 116.4(2) . . yes C14 C7 C8 121.2(2) . . yes C14 C7 H7A 119.4 . . ? C8 C7 H7A 119.4 . . ? C9 C8 C7 115.2(2) . . yes C9 C8 C16 121.9(2) . . yes C7 C8 C16 122.8(2) . . yes C10 C9 C8 123.5(2) . . yes C10 C9 H9A 118.2 . . ? C8 C9 H9A 118.2 . . ? N1 C10 C9 118.8(2) . . yes N1 C10 C22 120.9(2) . . yes C9 C10 C22 120.1(2) . . yes C13 C12 C1 120.5(2) . . yes C13 C12 N1 117.4(2) . . yes C1 C12 N1 121.6(2) . . yes C12 C13 N5 120.6(2) . . yes C12 C13 C4 119.7(2) . . yes N5 C13 C4 119.6(2) . . yes C7 C14 N1 121.4(2) . . yes C7 C14 C6 119.7(2) . . yes N1 C14 C6 118.5(2) . . yes C21 C16 C17 118.1(2) . . yes C21 C16 C8 120.5(2) . . yes C17 C16 C8 121.4(2) . . yes C18 C17 C16 120.5(2) . . yes C18 C17 H17A 119.8 . . ? C16 C17 H17A 119.8 . . ? C19 C18 C17 120.8(2) . . yes C19 C18 H18A 119.6 . . ? C17 C18 H18A 119.6 . . ? C20 C19 C18 119.1(2) . . yes C20 C19 H19A 120.4 . . ? C18 C19 H19A 120.4 . . ? C19 C20 C21 120.7(3) . . yes C19 C20 H20A 119.7 . . ? C21 C20 H20A 119.7 . . ? C20 C21 C16 120.7(3) . . yes C20 C21 H21A 119.6 . . ? C16 C21 H21A 119.6 . . ? C27 C22 C23 119.5(2) . . yes C27 C22 C10 120.8(2) . . yes C23 C22 C10 119.5(2) . . yes C24 C23 C22 119.3(3) . . yes C24 C23 H23A 120.3 . . ? C22 C23 H23A 120.4 . . ? C25 C24 C23 120.8(3) . . yes C25 C24 H24A 119.6 . . ? C23 C24 H24A 119.6 . . ? C26 C25 C24 119.8(3) . . yes C26 C25 H25A 120.1 . . ? C24 C25 H25A 120.1 . . ? C27 C26 C25 120.1(3) . . yes C27 C26 H26A 119.9 . . ? C25 C26 H26A 119.9 . . ? C26 C27 C22 120.6(2) . . yes C26 C27 H27A 119.7 . . ? C22 C27 H27A 119.7 . . ? O1 S1 O2 116.58(16) . . yes O1 S1 O3 114.00(15) . . yes O2 S1 O3 114.32(13) . . yes O1 S1 C30 103.32(15) . . yes O2 S1 C30 103.48(13) . . yes O3 S1 C30 102.70(13) . . yes F1 C30 F3 108.6(2) . . yes F1 C30 F2 106.8(2) . . yes F3 C30 F2 107.2(2) . . yes F1 C30 S1 111.6(2) . . yes F3 C30 S1 112.7(2) . . yes F2 C30 S1 109.70(19) . . yes C99 O98 H98O 98.7 . . ? C99 O98 H99O 89.1 . . ? H98O O98 H99O 29.9 . . ? C99 O99 H98O 87.8 . . ? C99 O99 H99O 96.8 . . ? H98O O99 H99O 27.9 . . ? O98 C99 O99 32.7(4) . . yes O98 C99 H99A 109.2 . . ? O99 C99 H99A 110.1 . . ? O98 C99 H99B 109.7 . . ? O99 C99 H99B 79.3 . . ? H99A C99 H99B 109.5 . . ? O98 C99 H99C 109.5 . . ? O99 C99 H99C 133.2 . . ? H99A C99 H99C 109.5 . . ? H99B C99 H99C 109.5 . . ? O98 C99 H99D 113.4 . . ? O99 C99 H99D 109.3 . . ? H99A C99 H99D 8.4 . . ? H99B C99 H99D 101.0 . . ? H99C C99 H99D 113.4 . . ? O98 C99 H99E 130.4 . . ? O99 C99 H99E 109.0 . . ? H99A C99 H99E 116.2 . . ? H99B C99 H99E 36.6 . . ? H99C C99 H99E 73.6 . . ? H99D C99 H99E 109.5 . . ? O98 C99 H99F 78.7 . . ? O99 C99 H99F 110.0 . . ? H99A C99 H99F 101.7 . . ? H99B C99 H99F 142.0 . . ? H99C C99 H99F 37.3 . . ? H99D C99 H99F 109.5 . . ? H99E C99 H99F 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 C12 C1 C2 C3 0.4(4) . . . . yes C1 C2 C3 C4 2.3(4) . . . . yes C2 C3 C4 O4 175.1(2) . . . . yes C2 C3 C4 C13 -1.7(4) . . . . yes C13 N5 C6 O6 172.0(3) . . . . yes C13 N5 C6 C14 -12.3(3) . . . . yes C14 C7 C8 C9 -8.4(3) . . . . yes C14 C7 C8 C16 176.8(2) . . . . yes C7 C8 C9 C10 6.5(4) . . . . yes C16 C8 C9 C10 -178.7(2) . . . . yes C14 N1 C10 C9 -14.2(3) . . . . yes C12 N1 C10 C9 159.5(2) . . . . yes C14 N1 C10 C22 160.3(2) . . . . yes C12 N1 C10 C22 -26.0(3) . . . . yes C8 C9 C10 N1 4.8(4) . . . . yes C8 C9 C10 C22 -169.8(2) . . . . yes C2 C1 C12 C13 -3.8(4) . . . . yes C2 C1 C12 N1 -176.3(2) . . . . yes C10 N1 C12 C13 163.9(2) . . . . yes C14 N1 C12 C13 -22.4(3) . . . . yes C10 N1 C12 C1 -23.3(3) . . . . yes C14 N1 C12 C1 150.4(2) . . . . yes C1 C12 C13 N5 -170.5(2) . . . . yes N1 C12 C13 N5 2.3(3) . . . . yes C1 C12 C13 C4 4.3(4) . . . . yes N1 C12 C13 C4 177.2(2) . . . . yes C6 N5 C13 C12 15.5(4) . . . . yes C6 N5 C13 C4 -159.3(2) . . . . yes O4 C4 C13 C12 -178.7(2) . . . . yes C3 C4 C13 C12 -1.6(4) . . . . yes O4 C4 C13 N5 -3.7(3) . . . . yes C3 C4 C13 N5 173.4(2) . . . . yes C8 C7 C14 N1 -0.9(4) . . . . yes C8 C7 C14 C6 172.1(2) . . . . yes C10 N1 C14 C7 12.5(3) . . . . yes C12 N1 C14 C7 -161.5(2) . . . . yes C10 N1 C14 C6 -160.6(2) . . . . yes C12 N1 C14 C6 25.4(3) . . . . yes O6 C6 C14 C7 -5.7(4) . . . . yes N5 C6 C14 C7 178.4(2) . . . . yes O6 C6 C14 N1 167.6(2) . . . . yes N5 C6 C14 N1 -8.3(3) . . . . yes C9 C8 C16 C21 4.0(4) . . . . yes C7 C8 C16 C21 178.5(2) . . . . yes C9 C8 C16 C17 -174.9(2) . . . . yes C7 C8 C16 C17 -0.4(4) . . . . yes C21 C16 C17 C18 -0.9(4) . . . . yes C8 C16 C17 C18 178.0(2) . . . . yes C16 C17 C18 C19 0.4(4) . . . . yes C17 C18 C19 C20 0.4(4) . . . . yes C18 C19 C20 C21 -0.5(5) . . . . yes C19 C20 C21 C16 -0.1(5) . . . . yes C17 C16 C21 C20 0.8(4) . . . . yes C8 C16 C21 C20 -178.1(3) . . . . yes N1 C10 C22 C27 -44.4(3) . . . . yes C9 C10 C22 C27 130.0(3) . . . . yes N1 C10 C22 C23 140.3(3) . . . . yes C9 C10 C22 C23 -45.2(4) . . . . yes C27 C22 C23 C24 0.1(4) . . . . yes C10 C22 C23 C24 175.4(3) . . . . yes C22 C23 C24 C25 0.4(5) . . . . yes C23 C24 C25 C26 -0.7(5) . . . . yes C24 C25 C26 C27 0.5(5) . . . . yes C25 C26 C27 C22 0.1(4) . . . . yes C23 C22 C27 C26 -0.4(4) . . . . yes C10 C22 C27 C26 -175.6(3) . . . . yes O1 S1 C30 F1 66.6(3) . . . . yes O2 S1 C30 F1 -55.4(2) . . . . yes O3 S1 C30 F1 -174.6(2) . . . . yes O1 S1 C30 F3 -55.9(3) . . . . yes O2 S1 C30 F3 -177.8(2) . . . . yes O3 S1 C30 F3 62.9(2) . . . . yes O1 S1 C30 F2 -175.2(2) . . . . yes O2 S1 C30 F2 62.8(2) . . . . yes O3 S1 C30 F2 -56.4(2) . . . . yes 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 O4 H4O O3 0.835(10) 1.968(13) 2.794(3) 170(4) . N5 H5N O6 0.863(10) 2.067(15) 2.882(3) 157(3) 2_566 O98 H98O O1 0.88 1.94 2.827(9) 179.9 . O99 H99O O1 0.90 1.97 2.869(10) 179.6 . _refine_diff_density_max 0.983 _refine_diff_density_min -0.378 _refine_diff_density_rms 0.190 _diffrn_attenuator_scale 14.50 _diffrn_orient_matrix_UB_11 0.088531 _diffrn_orient_matrix_UB_12 -0.065769 _diffrn_orient_matrix_UB_13 -0.013375 _diffrn_orient_matrix_UB_21 0.086679 _diffrn_orient_matrix_UB_22 0.055719 _diffrn_orient_matrix_UB_23 0.041012 _diffrn_orient_matrix_UB_31 -0.043621 _diffrn_orient_matrix_UB_32 -0.043649 _diffrn_orient_matrix_UB_33 0.050385 loop_ _diffrn_oricheck_refln_index_h _diffrn_oricheck_refln_index_k _diffrn_oricheck_refln_index_l 3 -3 3 10 4 1 13 0 6 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 3 -3 3 10 4 1 13 0 6