# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2010 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_name 'Teply, Filip' _publ_contact_author_email teply@uochb.cas.cz _publ_section_title ; Monocationic N-heteroaromatics by [2+2+2] cycloaddition ; loop_ _publ_author_name F.Teply M.Cizkova V.Kolivoska I.Cisarova D.Saman L.Pospisil # Attachment '- compound 8 X-ray.cif' data_zel-roz-ccl2-et2o-uochb _database_code_depnum_ccdc_archive 'CCDC 736009' #TrackingRef '- compound 8 X-ray.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H16 N, C F3 O3 S' _chemical_formula_sum 'C19 H16 F3 N O3 S' _chemical_formula_weight 395.39 _chemical_compound_source 'synthesized by the authors' 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' F F 0.0171 0.0103 '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 21/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 7.4866(2) _cell_length_b 14.3369(2) _cell_length_c 17.3851(3) _cell_angle_alpha 90.00 _cell_angle_beta 100.0166(9) _cell_angle_gamma 90.00 _cell_volume 1837.58(6) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 4377 _cell_measurement_theta_min 1 _cell_measurement_theta_max 27,5 _exptl_crystal_description prism _exptl_crystal_colour green _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.429 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 816 _exptl_absorpt_coefficient_mu 0.225 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 'Nonius KappaCCD area detector' _diffrn_measurement_method '\f and \w scans to fill the Ewald sphere' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 37823 _diffrn_reflns_av_R_equivalents 0.040 _diffrn_reflns_av_sigmaI/netI 0.0197 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.85 _diffrn_reflns_theta_max 27.52 _reflns_number_total 4219 _reflns_number_gt 3558 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997)' _computing_cell_refinement 'COLLECT and DENZO' _computing_data_reduction 'COLLECT and DENZO' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _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^)+(0.0549P)^2^+0.7320P] 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 4219 _refine_ls_number_parameters 245 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0482 _refine_ls_R_factor_gt 0.0393 _refine_ls_wR_factor_ref 0.1099 _refine_ls_wR_factor_gt 0.1022 _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_restrained_S_all 1.044 _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 C1 C 0.22156(18) 0.34479(10) -0.01900(8) 0.0280(3) Uani 1 1 d . . . N2 N 0.17185(15) 0.28814(8) 0.03682(7) 0.0297(3) Uani 1 1 d . . . C3 C 0.1517(2) 0.19528(11) 0.02466(10) 0.0392(4) Uani 1 1 d . . . H3 H 0.1185 0.1569 0.0644 0.047 Uiso 1 1 calc R . . C4 C 0.1786(2) 0.15570(11) -0.04425(11) 0.0442(4) Uani 1 1 d . . . H4 H 0.1639 0.0904 -0.0522 0.053 Uiso 1 1 calc R . . C5 C 0.2271(2) 0.21138(12) -0.10179(10) 0.0412(4) Uani 1 1 d . . . H5 H 0.2452 0.1848 -0.1499 0.049 Uiso 1 1 calc R . . C6 C 0.2492(2) 0.30616(11) -0.08922(9) 0.0342(3) Uani 1 1 d . . . H6 H 0.2833 0.3449 -0.1286 0.041 Uiso 1 1 calc R . . C7 C 0.24145(19) 0.44172(10) -0.00310(8) 0.0299(3) Uani 1 1 d . . . C8 C 0.25937(19) 0.52407(10) 0.00824(8) 0.0297(3) Uani 1 1 d . . . C9 C 0.27815(18) 0.62216(10) 0.02154(8) 0.0281(3) Uani 1 1 d . . . C10 C 0.2582(2) 0.65992(11) 0.09384(8) 0.0333(3) Uani 1 1 d . . . H10 H 0.2317 0.6203 0.1342 0.040 Uiso 1 1 calc R . . C11 C 0.2771(2) 0.75490(11) 0.10637(9) 0.0364(3) Uani 1 1 d . . . H11 H 0.2637 0.7799 0.1556 0.044 Uiso 1 1 calc R . . C12 C 0.3156(2) 0.81490(10) 0.04793(9) 0.0341(3) Uani 1 1 d . . . C13 C 0.33315(19) 0.77663(10) -0.02405(9) 0.0323(3) Uani 1 1 d . . . H13 H 0.3580 0.8164 -0.0646 0.039 Uiso 1 1 calc R . . C14 C 0.31510(19) 0.68174(10) -0.03749(8) 0.0295(3) Uani 1 1 d . . . H14 H 0.3278 0.6569 -0.0869 0.035 Uiso 1 1 calc R . . C15 C 0.1392(2) 0.32825(12) 0.11183(9) 0.0360(3) Uani 1 1 d . . . H15A H 0.0651 0.2842 0.1369 0.043 Uiso 1 1 calc R . . H15B H 0.0697 0.3870 0.1013 0.043 Uiso 1 1 calc R . . C16 C 0.3166(2) 0.34803(12) 0.16776(9) 0.0373(3) Uani 1 1 d . . . H16A H 0.3918 0.3911 0.1423 0.045 Uiso 1 1 calc R . . H16B H 0.2892 0.3791 0.2152 0.045 Uiso 1 1 calc R . . C17 C 0.4191(2) 0.26251(12) 0.19027(8) 0.0376(4) Uani 1 1 d . . . C18 C 0.4983(2) 0.19204(14) 0.20549(10) 0.0456(4) Uani 1 1 d . . . H18 H 0.5622 0.1352 0.2178 0.055 Uiso 1 1 calc R . . C19 C 0.3377(3) 0.91821(12) 0.06216(12) 0.0474(4) Uani 1 1 d . . . H19A H 0.3679 0.9484 0.0155 0.071 Uiso 1 1 calc R . . H19B H 0.4354 0.9292 0.1066 0.071 Uiso 1 1 calc R . . H19C H 0.2241 0.9442 0.0736 0.071 Uiso 1 1 calc R . . C20 C 0.1136(2) -0.01434(11) 0.25365(9) 0.0407(4) Uani 1 1 d . . . S1 S -0.05822(5) 0.05908(3) 0.19690(2) 0.03561(12) Uani 1 1 d . . . F1 F 0.1069(2) -0.00820(9) 0.32977(6) 0.0729(4) Uani 1 1 d . . . F2 F 0.27962(16) 0.00925(10) 0.24498(8) 0.0722(4) Uani 1 1 d . . . F3 F 0.08940(15) -0.10390(7) 0.23514(6) 0.0509(3) Uani 1 1 d . . . O1 O -0.22373(19) 0.01811(10) 0.21286(10) 0.0632(4) Uani 1 1 d . . . O2 O -0.0168(2) 0.15068(8) 0.22719(8) 0.0586(4) Uani 1 1 d . . . O3 O -0.02906(18) 0.04521(8) 0.11843(7) 0.0462(3) 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 C1 0.0237(6) 0.0288(7) 0.0302(7) 0.0037(5) 0.0009(5) 0.0013(5) N2 0.0240(6) 0.0323(6) 0.0318(6) 0.0046(5) 0.0023(5) -0.0001(5) C3 0.0306(8) 0.0321(8) 0.0518(9) 0.0100(7) -0.0015(7) -0.0044(6) C4 0.0385(9) 0.0302(8) 0.0578(10) -0.0058(7) -0.0087(7) -0.0009(6) C5 0.0392(9) 0.0408(8) 0.0394(8) -0.0095(7) -0.0047(7) 0.0058(7) C6 0.0314(7) 0.0385(8) 0.0310(7) -0.0002(6) 0.0006(6) 0.0027(6) C7 0.0285(7) 0.0315(7) 0.0295(7) 0.0026(5) 0.0041(5) 0.0020(5) C8 0.0266(7) 0.0331(7) 0.0288(7) 0.0026(5) 0.0030(5) 0.0021(5) C9 0.0234(6) 0.0292(7) 0.0308(7) 0.0017(5) 0.0022(5) 0.0031(5) C10 0.0361(8) 0.0355(8) 0.0283(7) 0.0033(6) 0.0058(6) 0.0038(6) C11 0.0406(8) 0.0369(8) 0.0314(7) -0.0034(6) 0.0052(6) 0.0076(6) C12 0.0294(7) 0.0303(7) 0.0417(8) 0.0001(6) 0.0039(6) 0.0061(6) C13 0.0286(7) 0.0326(7) 0.0357(7) 0.0065(6) 0.0056(6) 0.0029(6) C14 0.0264(7) 0.0335(7) 0.0289(7) 0.0010(5) 0.0052(5) 0.0031(5) C15 0.0314(8) 0.0449(8) 0.0339(7) 0.0073(6) 0.0116(6) 0.0056(6) C16 0.0383(8) 0.0451(9) 0.0289(7) -0.0015(6) 0.0070(6) 0.0068(7) C17 0.0339(8) 0.0522(10) 0.0264(7) 0.0029(6) 0.0043(6) 0.0030(7) C18 0.0417(9) 0.0551(10) 0.0392(9) 0.0088(8) 0.0047(7) 0.0085(8) C19 0.0518(10) 0.0309(8) 0.0598(11) -0.0043(7) 0.0101(8) 0.0040(7) C20 0.0495(10) 0.0364(8) 0.0338(8) 0.0009(6) 0.0005(7) -0.0082(7) S1 0.0412(2) 0.02698(19) 0.0408(2) 0.00383(14) 0.01307(16) -0.00060(14) F1 0.1264(12) 0.0575(7) 0.0289(5) 0.0037(5) -0.0030(6) -0.0214(7) F2 0.0412(6) 0.0763(9) 0.0924(10) 0.0272(7) -0.0075(6) -0.0096(6) F3 0.0612(7) 0.0311(5) 0.0564(6) -0.0003(4) -0.0009(5) 0.0061(4) O1 0.0461(8) 0.0477(8) 0.1025(12) 0.0252(7) 0.0318(7) 0.0035(6) O2 0.0882(11) 0.0276(6) 0.0632(9) -0.0044(6) 0.0219(8) -0.0012(6) O3 0.0600(8) 0.0448(7) 0.0317(6) 0.0052(5) 0.0025(5) -0.0020(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N2 1.3659(18) . ? C1 C6 1.388(2) . ? C1 C7 1.4197(19) . ? N2 C3 1.352(2) . ? N2 C15 1.4840(19) . ? C3 C4 1.372(3) . ? C3 H3 0.9500 . ? C4 C5 1.377(3) . ? C4 H4 0.9500 . ? C5 C6 1.382(2) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 C8 1.201(2) . ? C8 C9 1.428(2) . ? C9 C14 1.3993(19) . ? C9 C10 1.400(2) . ? C10 C11 1.382(2) . ? C10 H10 0.9500 . ? C11 C12 1.399(2) . ? C11 H11 0.9500 . ? C12 C13 1.393(2) . ? C12 C19 1.506(2) . ? C13 C14 1.383(2) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? C15 C16 1.530(2) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 C17 1.463(2) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 C18 1.178(2) . ? C18 H18 0.9500 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 F2 1.321(2) . ? C20 F3 1.3285(19) . ? C20 F1 1.3360(19) . ? C20 S1 1.8154(18) . ? S1 O2 1.4287(13) . ? S1 O3 1.4324(12) . ? S1 O1 1.4412(13) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 C1 C6 119.22(13) . . ? N2 C1 C7 118.43(13) . . ? C6 C1 C7 122.34(13) . . ? C3 N2 C1 120.73(13) . . ? C3 N2 C15 119.21(13) . . ? C1 N2 C15 120.06(12) . . ? N2 C3 C4 120.97(15) . . ? N2 C3 H3 119.5 . . ? C4 C3 H3 119.5 . . ? C3 C4 C5 119.47(15) . . ? C3 C4 H4 120.3 . . ? C5 C4 H4 120.3 . . ? C4 C5 C6 119.65(15) . . ? C4 C5 H5 120.2 . . ? C6 C5 H5 120.2 . . ? C5 C6 C1 119.95(15) . . ? C5 C6 H6 120.0 . . ? C1 C6 H6 120.0 . . ? C8 C7 C1 178.13(16) . . ? C7 C8 C9 179.24(16) . . ? C14 C9 C10 119.20(13) . . ? C14 C9 C8 120.59(13) . . ? C10 C9 C8 120.21(13) . . ? C11 C10 C9 119.89(14) . . ? C11 C10 H10 120.1 . . ? C9 C10 H10 120.1 . . ? C10 C11 C12 121.31(14) . . ? C10 C11 H11 119.3 . . ? C12 C11 H11 119.3 . . ? C13 C12 C11 118.27(14) . . ? C13 C12 C19 120.67(15) . . ? C11 C12 C19 121.06(15) . . ? C14 C13 C12 121.16(14) . . ? C14 C13 H13 119.4 . . ? C12 C13 H13 119.4 . . ? C13 C14 C9 120.17(13) . . ? C13 C14 H14 119.9 . . ? C9 C14 H14 119.9 . . ? N2 C15 C16 111.86(12) . . ? N2 C15 H15A 109.2 . . ? C16 C15 H15A 109.2 . . ? N2 C15 H15B 109.2 . . ? C16 C15 H15B 109.2 . . ? H15A C15 H15B 107.9 . . ? C17 C16 C15 111.82(14) . . ? C17 C16 H16A 109.3 . . ? C15 C16 H16A 109.3 . . ? C17 C16 H16B 109.3 . . ? C15 C16 H16B 109.3 . . ? H16A C16 H16B 107.9 . . ? C18 C17 C16 177.22(18) . . ? C17 C18 H18 180.0 . . ? C12 C19 H19A 109.5 . . ? C12 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C12 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? F2 C20 F3 108.14(15) . . ? F2 C20 F1 107.13(14) . . ? F3 C20 F1 106.06(13) . . ? F2 C20 S1 112.41(11) . . ? F3 C20 S1 112.01(11) . . ? F1 C20 S1 110.77(13) . . ? O2 S1 O3 114.79(8) . . ? O2 S1 O1 116.27(9) . . ? O3 S1 O1 113.91(9) . . ? O2 S1 C20 104.17(8) . . ? O3 S1 C20 103.06(8) . . ? O1 S1 C20 102.17(8) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.52 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.371 _refine_diff_density_min -0.387 _refine_diff_density_rms 0.045 #===END # Attachment '- compound 12 X-ray.cif' data_cerv-roz-etoac-benz-uochb _database_code_depnum_ccdc_archive 'CCDC 736010' #TrackingRef '- compound 12 X-ray.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C17 H18 N S, C F3 O3 S' _chemical_formula_sum 'C18 H18 F3 N O3 S2' _chemical_formula_weight 417.45 _chemical_compound_source 'synthesized by the authors' 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 orthorhombic _symmetry_space_group_name_H-M 'P c a 21' _symmetry_space_group_name_Hall 'P 2c -2ac' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x+1/2, y, z+1/2' 'x+1/2, -y, z' _cell_length_a 12.1750(2) _cell_length_b 10.9843(2) _cell_length_c 14.5988(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1952.35(5) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 2559 _cell_measurement_theta_min 1 _cell_measurement_theta_max 27.5 _exptl_crystal_description plate _exptl_crystal_colour green _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.420 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 864 _exptl_absorpt_coefficient_mu 0.318 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 'Nonius KappaCCD area detector' _diffrn_measurement_method '\f and \w scans to fill the Ewald sphere' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 36253 _diffrn_reflns_av_R_equivalents 0.0330 _diffrn_reflns_av_sigmaI/netI 0.0169 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.50 _diffrn_reflns_theta_max 27.48 _reflns_number_total 4275 _reflns_number_gt 4051 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997)' _computing_cell_refinement 'COLLECT and DENZO' _computing_data_reduction 'COLLECT and DENZO' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _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^)+(0.0502P)^2^+0.8053P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.50(6) _refine_ls_number_reflns 4275 _refine_ls_number_parameters 245 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0362 _refine_ls_R_factor_gt 0.0333 _refine_ls_wR_factor_ref 0.0893 _refine_ls_wR_factor_gt 0.0864 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.041 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.09263(15) 0.28850(17) 0.34773(15) 0.0269(4) Uani 1 1 d . . . S2 S 0.23232(4) 0.29343(4) 0.36168(4) 0.02832(11) Uani 1 1 d . . . C3 C 0.21595(16) 0.35019(17) 0.47199(13) 0.0239(4) Uani 1 1 d . . . C4 C 0.29648(17) 0.38483(19) 0.53456(14) 0.0283(4) Uani 1 1 d . . . H4 H 0.3724 0.3762 0.5209 0.034 Uiso 1 1 calc R . . C5 C 0.2616(2) 0.43249(18) 0.61772(15) 0.0313(4) Uani 1 1 d . . . H5 H 0.3147 0.4578 0.6614 0.038 Uiso 1 1 calc R . . C6 C 0.15031(17) 0.4439(2) 0.63840(15) 0.0308(4) Uani 1 1 d . . . H6 H 0.1293 0.4771 0.6959 0.037 Uiso 1 1 calc R . . C7 C 0.07047(16) 0.40833(19) 0.57773(14) 0.0275(4) Uani 1 1 d . . . H7 H -0.0052 0.4152 0.5926 0.033 Uiso 1 1 calc R . . C8 C 0.10429(16) 0.36173(17) 0.49332(13) 0.0235(4) Uani 1 1 d . . . N9 N 0.03736(14) 0.32511(16) 0.42039(12) 0.0248(3) Uani 1 1 d . . . C10 C 0.04497(17) 0.2524(2) 0.26367(15) 0.0312(4) Uani 1 1 d . . . C11 C 0.01140(19) 0.2251(2) 0.18950(16) 0.0352(5) Uani 1 1 d . . . C12 C -0.0284(2) 0.1929(2) 0.09820(15) 0.0419(6) Uani 1 1 d . . . H12A H 0.0327 0.1559 0.0632 0.050 Uiso 1 1 calc R . . H12B H -0.0505 0.2683 0.0660 0.050 Uiso 1 1 calc R . . C13 C -0.1246(2) 0.1054(2) 0.09815(18) 0.0462(6) Uani 1 1 d . . . H13A H -0.1878 0.1453 0.1285 0.055 Uiso 1 1 calc R . . H13B H -0.1459 0.0888 0.0339 0.055 Uiso 1 1 calc R . . C14 C -0.1029(3) -0.0126(3) 0.1447(2) 0.0554(7) Uani 1 1 d . . . H14A H -0.0767 0.0031 0.2078 0.067 Uiso 1 1 calc R . . H14B H -0.0442 -0.0567 0.1115 0.067 Uiso 1 1 calc R . . C15 C -0.2071(4) -0.0930(3) 0.1485(3) 0.0764(11) Uani 1 1 d . . . H15A H -0.2628 -0.0533 0.1867 0.115 Uiso 1 1 calc R . . H15B H -0.1886 -0.1725 0.1747 0.115 Uiso 1 1 calc R . . H15C H -0.2361 -0.1041 0.0864 0.115 Uiso 1 1 calc R . . C16 C -0.08337(16) 0.3297(2) 0.42343(15) 0.0286(4) Uani 1 1 d . . . H16A H -0.1126 0.3257 0.3602 0.034 Uiso 1 1 calc R . . H16B H -0.1068 0.4081 0.4506 0.034 Uiso 1 1 calc R . . C17 C -0.13145(17) 0.2250(2) 0.47961(15) 0.0314(4) Uani 1 1 d . . . H17A H -0.1037 0.2308 0.5432 0.038 Uiso 1 1 calc R . . H17B H -0.2124 0.2337 0.4816 0.038 Uiso 1 1 calc R . . C18 C -0.10409(19) 0.1045(2) 0.44277(16) 0.0355(5) Uani 1 1 d . . . C19 C -0.0808(2) 0.0079(2) 0.41373(19) 0.0477(6) Uani 1 1 d . . . H19 H -0.0621 -0.0700 0.3903 0.057 Uiso 1 1 calc R . . C20 C 0.13582(19) 0.7562(2) 0.28069(16) 0.0372(5) Uani 1 1 d . . . F1 F 0.22862(15) 0.7103(2) 0.24592(16) 0.0741(6) Uani 1 1 d . . . F2 F 0.16235(16) 0.85564(15) 0.32674(13) 0.0643(5) Uani 1 1 d . . . F3 F 0.07362(15) 0.79058(16) 0.21088(11) 0.0569(4) Uani 1 1 d . . . O1 O 0.04832(16) 0.54510(15) 0.29101(13) 0.0458(4) Uani 1 1 d . . . O2 O 0.14810(15) 0.62276(16) 0.42329(13) 0.0446(4) Uani 1 1 d . . . O3 O -0.02890(14) 0.70811(17) 0.38217(13) 0.0449(4) Uani 1 1 d . . . S1 S 0.06840(4) 0.64507(4) 0.35259(4) 0.02652(11) 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 C1 0.0275(8) 0.0294(8) 0.0238(9) 0.0015(8) 0.0002(8) -0.0006(6) S2 0.0256(2) 0.0356(2) 0.0238(2) -0.0031(2) 0.0030(2) 0.00051(16) C3 0.0255(9) 0.0244(9) 0.0217(9) 0.0020(7) 0.0018(7) 0.0005(7) C4 0.0277(9) 0.0301(10) 0.0273(10) 0.0032(8) -0.0014(8) -0.0024(7) C5 0.0376(12) 0.0324(9) 0.0239(10) 0.0017(8) -0.0028(8) -0.0054(9) C6 0.0384(11) 0.0325(10) 0.0216(9) -0.0019(8) 0.0019(8) -0.0005(8) C7 0.0284(10) 0.0284(9) 0.0257(9) -0.0008(8) 0.0033(7) -0.0002(7) C8 0.0241(9) 0.0243(8) 0.0222(9) 0.0033(7) 0.0007(7) -0.0003(7) N9 0.0255(8) 0.0261(7) 0.0229(8) 0.0017(6) -0.0008(6) -0.0004(6) C10 0.0314(10) 0.0369(11) 0.0253(10) -0.0011(8) 0.0004(8) -0.0033(8) C11 0.0380(11) 0.0404(11) 0.0272(11) 0.0000(9) 0.0018(9) -0.0082(9) C12 0.0536(15) 0.0485(14) 0.0236(11) -0.0004(9) -0.0044(10) -0.0118(11) C13 0.0506(15) 0.0515(15) 0.0365(13) -0.0047(11) -0.0075(11) -0.0024(12) C14 0.0696(19) 0.0514(15) 0.0453(15) -0.0018(12) -0.0047(13) 0.0014(14) C15 0.105(3) 0.0465(17) 0.077(2) -0.0144(16) 0.022(2) -0.0288(18) C16 0.0223(9) 0.0357(10) 0.0278(10) 0.0011(8) -0.0014(7) 0.0046(8) C17 0.0248(9) 0.0391(11) 0.0302(10) 0.0010(9) 0.0009(8) -0.0021(8) C18 0.0361(11) 0.0407(12) 0.0296(10) 0.0082(9) -0.0031(9) -0.0056(9) C19 0.0629(17) 0.0391(13) 0.0410(14) 0.0053(11) -0.0015(11) 0.0036(11) C20 0.0373(11) 0.0450(12) 0.0293(11) 0.0102(10) -0.0013(9) -0.0041(10) F1 0.0466(10) 0.0990(16) 0.0767(14) 0.0299(11) 0.0324(9) 0.0095(9) F2 0.0859(13) 0.0494(9) 0.0575(11) 0.0156(7) -0.0172(9) -0.0330(8) F3 0.0733(11) 0.0650(10) 0.0324(8) 0.0197(7) -0.0147(8) -0.0007(8) O1 0.0577(11) 0.0320(8) 0.0477(10) -0.0065(7) -0.0103(8) 0.0013(7) O2 0.0510(10) 0.0457(9) 0.0369(9) 0.0157(7) -0.0136(8) -0.0047(8) O3 0.0315(8) 0.0555(10) 0.0476(11) -0.0025(8) 0.0131(7) 0.0036(7) S1 0.0259(2) 0.0285(2) 0.0252(2) 0.0023(2) 0.0005(2) -0.00232(16) _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 C1 N9 1.319(3) . ? C1 C10 1.414(3) . ? C1 S2 1.7138(19) . ? S2 C3 1.738(2) . ? C3 C4 1.393(3) . ? C3 C8 1.400(3) . ? C4 C5 1.389(3) . ? C4 H4 0.9500 . ? C5 C6 1.394(3) . ? C5 H5 0.9500 . ? C6 C7 1.372(3) . ? C6 H6 0.9500 . ? C7 C8 1.396(3) . ? C7 H7 0.9500 . ? C8 N9 1.400(3) . ? N9 C16 1.471(3) . ? C10 C11 1.196(3) . ? C11 C12 1.462(3) . ? C12 C13 1.514(4) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.487(4) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C15 1.547(5) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 C17 1.529(3) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 C18 1.467(3) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 C19 1.176(4) . ? C19 H19 0.9500 . ? C20 F2 1.323(3) . ? C20 F3 1.325(3) . ? C20 F1 1.337(3) . ? C20 S1 1.807(2) . ? O1 S1 1.4400(18) . ? O2 S1 1.4377(17) . ? O3 S1 1.4385(17) . ? 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 N9 C1 C10 125.04(18) . . ? N9 C1 S2 113.65(15) . . ? C10 C1 S2 121.27(16) . . ? C1 S2 C3 90.44(10) . . ? C4 C3 C8 120.84(18) . . ? C4 C3 S2 128.66(15) . . ? C8 C3 S2 110.47(15) . . ? C5 C4 C3 117.46(19) . . ? C5 C4 H4 121.3 . . ? C3 C4 H4 121.3 . . ? C4 C5 C6 121.4(2) . . ? C4 C5 H5 119.3 . . ? C6 C5 H5 119.3 . . ? C7 C6 C5 121.6(2) . . ? C7 C6 H6 119.2 . . ? C5 C6 H6 119.2 . . ? C6 C7 C8 117.72(18) . . ? C6 C7 H7 121.1 . . ? C8 C7 H7 121.1 . . ? C7 C8 N9 127.22(18) . . ? C7 C8 C3 121.04(18) . . ? N9 C8 C3 111.71(17) . . ? C1 N9 C8 113.73(17) . . ? C1 N9 C16 122.97(17) . . ? C8 N9 C16 123.29(17) . . ? C11 C10 C1 175.2(2) . . ? C10 C11 C12 179.2(3) . . ? C11 C12 C13 114.2(2) . . ? C11 C12 H12A 108.7 . . ? C13 C12 H12A 108.7 . . ? C11 C12 H12B 108.7 . . ? C13 C12 H12B 108.7 . . ? H12A C12 H12B 107.6 . . ? C14 C13 C12 114.5(2) . . ? C14 C13 H13A 108.6 . . ? C12 C13 H13A 108.6 . . ? C14 C13 H13B 108.6 . . ? C12 C13 H13B 108.6 . . ? H13A C13 H13B 107.6 . . ? C13 C14 C15 111.6(3) . . ? C13 C14 H14A 109.3 . . ? C15 C14 H14A 109.3 . . ? C13 C14 H14B 109.3 . . ? C15 C14 H14B 109.3 . . ? H14A C14 H14B 108.0 . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? N9 C16 C17 111.91(17) . . ? N9 C16 H16A 109.2 . . ? C17 C16 H16A 109.2 . . ? N9 C16 H16B 109.2 . . ? C17 C16 H16B 109.2 . . ? H16A C16 H16B 107.9 . . ? C18 C17 C16 113.26(18) . . ? C18 C17 H17A 108.9 . . ? C16 C17 H17A 108.9 . . ? C18 C17 H17B 108.9 . . ? C16 C17 H17B 108.9 . . ? H17A C17 H17B 107.7 . . ? C19 C18 C17 179.1(3) . . ? C18 C19 H19 180.0 . . ? F2 C20 F3 107.2(2) . . ? F2 C20 F1 107.3(2) . . ? F3 C20 F1 107.4(2) . . ? F2 C20 S1 111.93(17) . . ? F3 C20 S1 112.33(16) . . ? F1 C20 S1 110.48(17) . . ? O2 S1 O3 114.98(12) . . ? O2 S1 O1 115.64(11) . . ? O3 S1 O1 114.50(11) . . ? O2 S1 C20 103.04(10) . . ? O3 S1 C20 102.91(11) . . ? O1 S1 C20 103.27(12) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.676 _refine_diff_density_min -0.254 _refine_diff_density_rms 0.045 #===END # Attachment '- compound 16 X-ray.cif' data_mc214-teply-uochb _database_code_depnum_ccdc_archive 'CCDC 736011' #TrackingRef '- compound 16 X-ray.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H18 N, C1 F3 O3 S' _chemical_formula_sum 'C21 H18 F3 N O3 S' _chemical_formula_weight 421.42 _chemical_compound_source 'synthesized by the authors' 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 monoclinic _symmetry_space_group_name_H-M 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 23.1671(5) _cell_length_b 10.5994(2) _cell_length_c 15.6896(3) _cell_angle_alpha 90.00 _cell_angle_beta 92.5160(13) _cell_angle_gamma 90.00 _cell_volume 3848.98(13) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 4603 _cell_measurement_theta_min 1 _cell_measurement_theta_max 27.5 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.454 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1744 _exptl_absorpt_coefficient_mu 0.220 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 'Nonius KappaCCD area detector' _diffrn_measurement_method '\f and \w scans to fill the Ewald sphere' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 30434 _diffrn_reflns_av_R_equivalents 0.035 _diffrn_reflns_av_sigmaI/netI 0.0240 _diffrn_reflns_limit_h_min -29 _diffrn_reflns_limit_h_max 30 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.76 _diffrn_reflns_theta_max 27.49 _reflns_number_total 4425 _reflns_number_gt 3684 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997)' _computing_cell_refinement 'COLLECT and DENZO' _computing_data_reduction 'COLLECT and DENZO' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _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^)+(0.0531P)^2^+4.1073P] 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 4425 _refine_ls_number_parameters 263 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0512 _refine_ls_R_factor_gt 0.0405 _refine_ls_wR_factor_ref 0.1105 _refine_ls_wR_factor_gt 0.1031 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.035 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.22826(7) 0.08182(16) 0.66595(10) 0.0278(3) Uani 1 1 d . . . H1 H 0.2138 0.1451 0.7022 0.033 Uiso 1 1 calc R . . C2 C 0.27051(7) 0.00033(17) 0.69717(10) 0.0317(4) Uani 1 1 d . . . H2 H 0.2847 0.0066 0.7548 0.038 Uiso 1 1 calc R . . C3 C 0.29215(7) -0.09084(18) 0.64369(11) 0.0341(4) Uani 1 1 d . . . H3 H 0.3205 -0.1492 0.6646 0.041 Uiso 1 1 calc R . . C4 C 0.27211(7) -0.09539(17) 0.56049(11) 0.0312(4) Uani 1 1 d . . . H4 H 0.2877 -0.1556 0.5229 0.037 Uiso 1 1 calc R . . N5 N 0.23058(5) -0.01554(13) 0.53108(8) 0.0257(3) Uani 1 1 d . . . C6 C 0.21034(7) -0.02238(16) 0.44016(10) 0.0292(3) Uani 1 1 d . . . H6A H 0.1711 -0.0593 0.4353 0.035 Uiso 1 1 calc R . . H6B H 0.2366 -0.0762 0.4079 0.035 Uiso 1 1 calc R . . C7 C 0.20964(7) 0.11017(16) 0.40475(10) 0.0301(3) Uani 1 1 d . . . H7A H 0.2490 0.1465 0.4091 0.036 Uiso 1 1 calc R . . H7B H 0.1964 0.1091 0.3439 0.036 Uiso 1 1 calc R . . C8 C 0.16909(7) 0.18891(15) 0.45547(10) 0.0266(3) Uani 1 1 d . . . C9 C 0.13636(7) 0.28511(17) 0.41782(11) 0.0321(4) Uani 1 1 d . . . H9 H 0.1409 0.3062 0.3596 0.039 Uiso 1 1 calc R . . C10 C 0.09711(8) 0.35023(17) 0.46505(11) 0.0346(4) Uani 1 1 d . . . H10 H 0.0764 0.4194 0.4403 0.042 Uiso 1 1 calc R . . C11 C 0.08798(7) 0.31481(16) 0.54843(11) 0.0313(4) Uani 1 1 d . . . H11 H 0.0592 0.3572 0.5789 0.038 Uiso 1 1 calc R . . C12 C 0.11988(7) 0.21875(14) 0.58873(10) 0.0250(3) Uani 1 1 d . . . C13 C 0.16328(6) 0.15883(15) 0.54218(9) 0.0239(3) Uani 1 1 d . . . C14 C 0.20654(6) 0.07242(15) 0.58190(9) 0.0238(3) Uani 1 1 d . . . C15 C 0.10313(6) 0.17831(15) 0.67543(10) 0.0249(3) Uani 1 1 d . . . C16 C 0.09714(7) 0.05088(15) 0.69550(10) 0.0271(3) Uani 1 1 d . . . H16 H 0.1061 -0.0115 0.6546 0.033 Uiso 1 1 calc R . . C17 C 0.07824(7) 0.01414(16) 0.77455(10) 0.0289(3) Uani 1 1 d . . . H17 H 0.0746 -0.0731 0.7870 0.035 Uiso 1 1 calc R . . C18 C 0.06452(6) 0.10282(17) 0.83592(10) 0.0291(3) Uani 1 1 d . . . C19 C 0.07065(7) 0.23002(17) 0.81578(11) 0.0316(4) Uani 1 1 d . . . H19 H 0.0619 0.2922 0.8569 0.038 Uiso 1 1 calc R . . C20 C 0.08934(7) 0.26774(16) 0.73658(10) 0.0282(3) Uani 1 1 d . . . H20 H 0.0927 0.3550 0.7241 0.034 Uiso 1 1 calc R . . C21 C 0.04292(8) 0.0623(2) 0.92097(11) 0.0371(4) Uani 1 1 d . . . H21A H 0.0015 0.0798 0.9226 0.056 Uiso 1 1 calc R . . H21B H 0.0636 0.1090 0.9667 0.056 Uiso 1 1 calc R . . H21C H 0.0497 -0.0284 0.9288 0.056 Uiso 1 1 calc R . . C22 C 0.06213(8) -0.33043(18) 0.62693(15) 0.0471(5) Uani 1 1 d . . . F1 F 0.03306(5) -0.22370(12) 0.63671(10) 0.0608(4) Uani 1 1 d . . . F2 F 0.04764(7) -0.40934(15) 0.68734(14) 0.0941(6) Uani 1 1 d . . . F3 F 0.04451(6) -0.38095(14) 0.55210(12) 0.0759(5) Uani 1 1 d . . . S1 S 0.139773(17) -0.30356(4) 0.63006(2) 0.02830(12) Uani 1 1 d . . . O1 O 0.16290(5) -0.42892(12) 0.62035(8) 0.0358(3) Uani 1 1 d . . . O2 O 0.14725(6) -0.22192(13) 0.55832(8) 0.0405(3) Uani 1 1 d . . . O3 O 0.15215(7) -0.24612(15) 0.71142(8) 0.0521(4) 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 C1 0.0242(7) 0.0370(9) 0.0222(7) -0.0018(6) 0.0018(6) -0.0036(6) C2 0.0258(8) 0.0444(10) 0.0246(8) 0.0048(7) -0.0016(6) -0.0037(7) C3 0.0259(8) 0.0432(10) 0.0330(9) 0.0066(7) -0.0002(7) 0.0046(7) C4 0.0254(8) 0.0370(9) 0.0314(8) 0.0006(7) 0.0041(6) 0.0036(7) N5 0.0219(6) 0.0325(7) 0.0229(6) -0.0006(5) 0.0023(5) -0.0001(5) C6 0.0275(8) 0.0384(9) 0.0217(7) -0.0047(7) 0.0010(6) 0.0014(7) C7 0.0286(8) 0.0411(9) 0.0206(7) 0.0011(6) 0.0033(6) -0.0018(7) C8 0.0245(7) 0.0317(8) 0.0238(7) 0.0003(6) 0.0012(6) -0.0050(6) C9 0.0330(8) 0.0369(9) 0.0264(8) 0.0057(7) 0.0011(7) -0.0043(7) C10 0.0358(9) 0.0314(8) 0.0366(9) 0.0078(7) 0.0003(7) 0.0017(7) C11 0.0303(8) 0.0298(8) 0.0339(9) 0.0001(7) 0.0035(7) 0.0017(7) C12 0.0239(7) 0.0261(7) 0.0249(7) -0.0020(6) 0.0012(6) -0.0030(6) C13 0.0221(7) 0.0270(7) 0.0227(7) -0.0003(6) 0.0003(6) -0.0035(6) C14 0.0204(7) 0.0289(8) 0.0224(7) 0.0004(6) 0.0029(5) -0.0042(6) C15 0.0199(7) 0.0308(8) 0.0240(7) -0.0024(6) 0.0017(6) -0.0012(6) C16 0.0268(7) 0.0292(8) 0.0255(8) -0.0028(6) 0.0037(6) -0.0005(6) C17 0.0264(8) 0.0333(8) 0.0269(8) 0.0013(6) 0.0023(6) -0.0034(6) C18 0.0195(7) 0.0444(9) 0.0234(7) -0.0008(7) 0.0009(6) -0.0026(7) C19 0.0269(8) 0.0404(9) 0.0278(8) -0.0091(7) 0.0035(6) -0.0007(7) C20 0.0275(8) 0.0292(8) 0.0279(8) -0.0040(6) 0.0015(6) -0.0004(6) C21 0.0304(8) 0.0567(11) 0.0246(8) 0.0006(8) 0.0047(7) -0.0045(8) C22 0.0346(10) 0.0317(9) 0.0764(15) 0.0032(9) 0.0164(10) 0.0051(8) F1 0.0369(6) 0.0393(6) 0.1073(11) -0.0053(7) 0.0150(7) 0.0122(5) F2 0.0737(10) 0.0569(9) 0.1575(17) 0.0400(10) 0.0729(11) 0.0101(8) F3 0.0384(7) 0.0583(8) 0.1290(14) -0.0330(9) -0.0204(8) 0.0031(6) S1 0.0289(2) 0.0321(2) 0.0240(2) 0.00136(15) 0.00231(15) 0.00351(16) O1 0.0341(6) 0.0368(7) 0.0364(7) -0.0003(5) 0.0011(5) 0.0099(5) O2 0.0448(7) 0.0429(7) 0.0344(7) 0.0107(6) 0.0078(6) 0.0011(6) O3 0.0712(10) 0.0543(9) 0.0300(7) -0.0113(6) -0.0073(6) 0.0119(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 C1 C2 1.379(2) . ? C1 C14 1.394(2) . ? C1 H1 0.9500 . ? C2 C3 1.388(2) . ? C2 H2 0.9500 . ? C3 C4 1.367(2) . ? C3 H3 0.9500 . ? C4 N5 1.348(2) . ? C4 H4 0.9500 . ? N5 C14 1.362(2) . ? N5 C6 1.484(2) . ? C6 C7 1.511(2) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.509(2) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.387(2) . ? C8 C13 1.410(2) . ? C9 C10 1.383(2) . ? C9 H9 0.9500 . ? C10 C11 1.386(2) . ? C10 H10 0.9500 . ? C11 C12 1.393(2) . ? C11 H11 0.9500 . ? C12 C13 1.419(2) . ? C12 C15 1.494(2) . ? C13 C14 1.475(2) . ? C15 C16 1.395(2) . ? C15 C20 1.396(2) . ? C16 C17 1.389(2) . ? C16 H16 0.9500 . ? C17 C18 1.392(2) . ? C17 H17 0.9500 . ? C18 C19 1.393(3) . ? C18 C21 1.508(2) . ? C19 C20 1.392(2) . ? C19 H19 0.9500 . ? C20 H20 0.9500 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 F2 1.318(3) . ? C22 F1 1.329(2) . ? C22 F3 1.338(3) . ? C22 S1 1.820(2) . ? S1 O3 1.4317(14) . ? S1 O2 1.4362(12) . ? S1 O1 1.4433(13) . ? 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 C1 C14 120.81(15) . . ? C2 C1 H1 119.6 . . ? C14 C1 H1 119.6 . . ? C1 C2 C3 119.40(15) . . ? C1 C2 H2 120.3 . . ? C3 C2 H2 120.3 . . ? C4 C3 C2 119.03(16) . . ? C4 C3 H3 120.5 . . ? C2 C3 H3 120.5 . . ? N5 C4 C3 120.82(16) . . ? N5 C4 H4 119.6 . . ? C3 C4 H4 119.6 . . ? C4 N5 C14 122.25(14) . . ? C4 N5 C6 119.30(13) . . ? C14 N5 C6 118.45(13) . . ? N5 C6 C7 107.81(13) . . ? N5 C6 H6A 110.1 . . ? C7 C6 H6A 110.1 . . ? N5 C6 H6B 110.1 . . ? C7 C6 H6B 110.1 . . ? H6A C6 H6B 108.5 . . ? C8 C7 C6 108.50(13) . . ? C8 C7 H7A 110.0 . . ? C6 C7 H7A 110.0 . . ? C8 C7 H7B 110.0 . . ? C6 C7 H7B 110.0 . . ? H7A C7 H7B 108.4 . . ? C9 C8 C13 120.24(15) . . ? C9 C8 C7 121.55(14) . . ? C13 C8 C7 118.15(14) . . ? C10 C9 C8 119.92(15) . . ? C10 C9 H9 120.0 . . ? C8 C9 H9 120.0 . . ? C9 C10 C11 120.12(16) . . ? C9 C10 H10 119.9 . . ? C11 C10 H10 119.9 . . ? C10 C11 C12 121.77(16) . . ? C10 C11 H11 119.1 . . ? C12 C11 H11 119.1 . . ? C11 C12 C13 117.86(14) . . ? C11 C12 C15 117.99(14) . . ? C13 C12 C15 123.97(14) . . ? C8 C13 C12 119.70(14) . . ? C8 C13 C14 117.15(13) . . ? C12 C13 C14 122.97(13) . . ? N5 C14 C1 117.57(14) . . ? N5 C14 C13 117.73(13) . . ? C1 C14 C13 124.43(14) . . ? C16 C15 C20 118.31(14) . . ? C16 C15 C12 121.05(14) . . ? C20 C15 C12 120.51(14) . . ? C17 C16 C15 120.75(15) . . ? C17 C16 H16 119.6 . . ? C15 C16 H16 119.6 . . ? C16 C17 C18 121.25(16) . . ? C16 C17 H17 119.4 . . ? C18 C17 H17 119.4 . . ? C17 C18 C19 117.88(15) . . ? C17 C18 C21 120.94(16) . . ? C19 C18 C21 121.17(15) . . ? C20 C19 C18 121.27(15) . . ? C20 C19 H19 119.4 . . ? C18 C19 H19 119.4 . . ? C19 C20 C15 120.53(16) . . ? C19 C20 H20 119.7 . . ? C15 C20 H20 119.7 . . ? C18 C21 H21A 109.5 . . ? C18 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C18 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? F2 C22 F1 108.10(16) . . ? F2 C22 F3 107.43(19) . . ? F1 C22 F3 107.79(18) . . ? F2 C22 S1 111.24(16) . . ? F1 C22 S1 111.65(14) . . ? F3 C22 S1 110.46(14) . . ? O3 S1 O2 114.59(9) . . ? O3 S1 O1 115.15(8) . . ? O2 S1 O1 114.45(8) . . ? O3 S1 C22 104.46(10) . . ? O2 S1 C22 103.07(9) . . ? O1 S1 C22 102.95(8) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.443 _refine_diff_density_min -0.507 _refine_diff_density_rms 0.049 #===END # Attachment '- compound 24 X-ray.cif' data_mc253-1-teply-uochb _database_code_depnum_ccdc_archive 'CCDC 736012' #TrackingRef '- compound 24 X-ray.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H8 N2' _chemical_formula_sum 'C12 H8 N2' _chemical_formula_weight 180.20 _chemical_compound_source 'synthesized by the authors' _chemical_absolute_configuration unk 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' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P n a 21' _symmetry_space_group_name_Hall 'P 2c -2n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x+1/2, y+1/2, z+1/2' 'x+1/2, -y+1/2, z' _cell_length_a 23.3925(2) _cell_length_b 6.2169(4) _cell_length_c 13.0456(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1897.21(17) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 2189 _cell_measurement_theta_min 1 _cell_measurement_theta_max 26. _exptl_crystal_description bar _exptl_crystal_colour colourless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.075 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.262 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 752 _exptl_absorpt_coefficient_mu 0.077 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 'Nonius KappaCCD area detector' _diffrn_measurement_method '\f and \w scans to fill the Ewald sphere' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 25711 _diffrn_reflns_av_R_equivalents 0.0790 _diffrn_reflns_av_sigmaI/netI 0.0430 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.74 _diffrn_reflns_theta_max 26.02 _reflns_number_total 3505 _reflns_number_gt 2484 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997)' _computing_cell_refinement 'COLLECT and DENZO' _computing_data_reduction 'COLLECT and DENZO' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _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^)+(0.0683P)^2^+0.2683P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 3(3) _refine_ls_number_reflns 3505 _refine_ls_number_parameters 253 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0893 _refine_ls_R_factor_gt 0.0517 _refine_ls_wR_factor_ref 0.1337 _refine_ls_wR_factor_gt 0.1121 _refine_ls_goodness_of_fit_ref 1.068 _refine_ls_restrained_S_all 1.067 _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 C11 C 0.37632(11) 1.0994(4) 0.1352(2) 0.0352(6) Uani 1 1 d . . . N12 N 0.36248(11) 1.3064(4) 0.1286(2) 0.0431(6) Uani 1 1 d . . . C13 C 0.40073(14) 1.4338(5) 0.0818(2) 0.0502(8) Uani 1 1 d . . . H13 H 0.3927 1.5831 0.0760 0.060 Uiso 1 1 calc R . . C14 C 0.45090(13) 1.3563(5) 0.0422(2) 0.0477(8) Uani 1 1 d . . . H14 H 0.4779 1.4487 0.0101 0.057 Uiso 1 1 calc R . . C15 C 0.46036(13) 1.1413(5) 0.0507(2) 0.0480(8) Uani 1 1 d . . . H15 H 0.4945 1.0830 0.0226 0.058 Uiso 1 1 calc R . . N16 N 0.42339(10) 1.0081(4) 0.09724(19) 0.0453(6) Uani 1 1 d . . . C17 C 0.33692(12) 0.9620(4) 0.1884(2) 0.0379(6) Uani 1 1 d . . . C18 C 0.30390(13) 0.8480(4) 0.2338(2) 0.0389(7) Uani 1 1 d . . . C19 C 0.26379(13) 0.7155(4) 0.2873(2) 0.0345(6) Uani 1 1 d . . . C21 C 0.36871(11) -0.0296(4) 0.4834(2) 0.0361(6) Uani 1 1 d . . . N22 N 0.37958(11) -0.2398(3) 0.4826(2) 0.0419(6) Uani 1 1 d . . . C23 C 0.33949(13) -0.3643(5) 0.5269(2) 0.0467(8) Uani 1 1 d . . . H23 H 0.3450 -0.5156 0.5279 0.056 Uiso 1 1 calc R . . C24 C 0.29111(13) -0.2808(5) 0.5704(3) 0.0450(8) Uani 1 1 d . . . H24 H 0.2631 -0.3708 0.6011 0.054 Uiso 1 1 calc R . . C25 C 0.28480(13) -0.0624(5) 0.5678(2) 0.0465(7) Uani 1 1 d . . . H25 H 0.2516 -0.0010 0.5978 0.056 Uiso 1 1 calc R . . N26 N 0.32324(10) 0.0686(4) 0.52512(19) 0.0436(6) Uani 1 1 d . . . C27 C 0.40932(12) 0.1062(4) 0.4323(2) 0.0404(7) Uani 1 1 d . . . C28 C 0.44286(12) 0.2172(4) 0.3864(2) 0.0388(7) Uani 1 1 d . . . C29 C 0.48380(12) 0.3397(4) 0.3291(2) 0.0365(7) Uani 1 1 d . . . C110 C 0.27851(13) 0.5047(4) 0.3158(2) 0.0413(7) Uani 1 1 d . . . H110 H 0.3155 0.4506 0.3003 0.050 Uiso 1 1 calc R . . C111 C 0.23969(13) 0.3761(4) 0.3659(2) 0.0440(7) Uani 1 1 d . . . H111 H 0.2500 0.2336 0.3846 0.053 Uiso 1 1 calc R . . C112 C 0.18575(14) 0.4527(5) 0.3893(2) 0.0477(8) Uani 1 1 d . . . H112 H 0.1592 0.3641 0.4248 0.057 Uiso 1 1 calc R . . C113 C 0.17062(13) 0.6596(5) 0.3605(3) 0.0502(8) Uani 1 1 d . . . H113 H 0.1335 0.7129 0.3760 0.060 Uiso 1 1 calc R . . C114 C 0.20920(12) 0.7878(4) 0.3098(3) 0.0405(7) Uani 1 1 d . . . H114 H 0.1982 0.9288 0.2897 0.049 Uiso 1 1 calc R . . C210 C 0.47130(12) 0.5488(4) 0.2977(2) 0.0419(7) Uani 1 1 d . . . H210 H 0.4358 0.6127 0.3156 0.050 Uiso 1 1 calc R . . C211 C 0.51078(14) 0.6630(5) 0.2405(2) 0.0460(7) Uani 1 1 d . . . H211 H 0.5021 0.8050 0.2187 0.055 Uiso 1 1 calc R . . C212 C 0.56225(14) 0.5730(5) 0.2152(2) 0.0503(8) Uani 1 1 d . . . H212 H 0.5890 0.6523 0.1754 0.060 Uiso 1 1 calc R . . C213 C 0.57553(13) 0.3665(5) 0.2474(3) 0.0498(8) Uani 1 1 d . . . H213 H 0.6115 0.3049 0.2306 0.060 Uiso 1 1 calc R . . C214 C 0.53661(13) 0.2511(4) 0.3037(3) 0.0415(7) Uani 1 1 d . . . H214 H 0.5458 0.1096 0.3256 0.050 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 C11 0.0307(15) 0.0390(16) 0.0360(14) 0.0008(12) -0.0030(13) -0.0016(12) N12 0.0447(15) 0.0418(13) 0.0427(14) -0.0005(11) 0.0078(13) 0.0007(11) C13 0.063(2) 0.0367(15) 0.0512(18) 0.0025(14) 0.0055(17) -0.0044(15) C14 0.050(2) 0.058(2) 0.0355(19) 0.0004(14) 0.0094(16) -0.0156(15) C15 0.0359(17) 0.066(2) 0.042(2) -0.0020(15) 0.0091(16) 0.0007(15) N16 0.0340(14) 0.0484(14) 0.0535(17) 0.0031(11) 0.0071(12) 0.0037(11) C17 0.0306(15) 0.0399(15) 0.0433(15) 0.0035(13) -0.0008(13) 0.0030(12) C18 0.0357(17) 0.0424(15) 0.0385(16) -0.0003(13) -0.0052(15) -0.0016(13) C19 0.0343(17) 0.0396(14) 0.0298(15) 0.0001(11) -0.0019(13) -0.0023(12) C21 0.0322(15) 0.0379(15) 0.0383(15) 0.0010(13) 0.0001(13) -0.0006(12) N22 0.0419(15) 0.0361(12) 0.0476(15) 0.0013(11) 0.0005(13) 0.0026(10) C23 0.055(2) 0.0365(16) 0.0483(17) 0.0051(13) -0.0071(17) -0.0048(14) C24 0.0393(19) 0.0552(18) 0.041(2) 0.0029(14) 0.0005(16) -0.0126(14) C25 0.0392(17) 0.0578(18) 0.0423(16) -0.0041(15) 0.0111(14) -0.0020(15) N26 0.0407(14) 0.0410(13) 0.0490(14) 0.0004(11) 0.0096(12) -0.0008(12) C27 0.0339(17) 0.0424(16) 0.0450(16) 0.0030(13) 0.0002(15) 0.0024(13) C28 0.0317(16) 0.0457(16) 0.0390(17) 0.0003(13) -0.0025(15) -0.0009(12) C29 0.0317(16) 0.0381(15) 0.0397(16) -0.0005(12) -0.0001(14) -0.0046(12) C110 0.0413(17) 0.0441(16) 0.0386(15) -0.0034(13) 0.0008(13) 0.0031(13) C111 0.0537(19) 0.0376(15) 0.0408(17) 0.0031(13) -0.0031(15) -0.0055(13) C112 0.053(2) 0.0493(17) 0.0408(17) 0.0031(14) 0.0025(15) -0.0129(15) C113 0.0360(17) 0.058(2) 0.056(2) -0.0043(16) 0.0061(16) -0.0005(14) C114 0.0354(18) 0.0370(14) 0.049(2) -0.0004(13) 0.0002(16) -0.0008(12) C210 0.0364(17) 0.0466(16) 0.0428(17) 0.0000(14) -0.0021(14) -0.0023(13) C211 0.051(2) 0.0384(15) 0.0485(17) 0.0044(13) -0.0039(16) -0.0052(14) C212 0.0410(19) 0.057(2) 0.053(2) 0.0112(15) 0.0027(15) -0.0112(15) C213 0.0377(18) 0.0533(19) 0.059(2) 0.0072(15) 0.0046(16) -0.0010(14) C214 0.0407(19) 0.0355(15) 0.048(2) 0.0051(13) 0.0008(16) -0.0011(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 C11 N12 1.330(3) . ? C11 N16 1.334(3) . ? C11 C17 1.436(4) . ? N12 C13 1.342(4) . ? C13 C14 1.370(4) . ? C13 H13 0.9500 . ? C14 C15 1.360(4) . ? C14 H14 0.9500 . ? C15 N16 1.343(4) . ? C15 H15 0.9500 . ? C17 C18 1.204(4) . ? C18 C19 1.430(4) . ? C19 C114 1.385(4) . ? C19 C110 1.405(4) . ? C21 N22 1.331(3) . ? C21 N26 1.342(3) . ? C21 C27 1.435(4) . ? N22 C23 1.346(4) . ? C23 C24 1.369(4) . ? C23 H23 0.9500 . ? C24 C25 1.366(4) . ? C24 H24 0.9500 . ? C25 N26 1.335(4) . ? C25 H25 0.9500 . ? C27 C28 1.204(4) . ? C28 C29 1.434(4) . ? C29 C214 1.392(4) . ? C29 C210 1.394(4) . ? C110 C111 1.375(4) . ? C110 H110 0.9500 . ? C111 C112 1.383(4) . ? C111 H111 0.9500 . ? C112 C113 1.386(4) . ? C112 H112 0.9500 . ? C113 C114 1.374(4) . ? C113 H113 0.9500 . ? C114 H114 0.9500 . ? C210 C211 1.383(4) . ? C210 H210 0.9500 . ? C211 C212 1.368(5) . ? C211 H211 0.9500 . ? C212 C213 1.386(4) . ? C212 H212 0.9500 . ? C213 C214 1.372(4) . ? C213 H213 0.9500 . ? C214 H214 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N12 C11 N16 126.1(3) . . ? N12 C11 C17 116.8(2) . . ? N16 C11 C17 117.1(2) . . ? C11 N12 C13 116.0(3) . . ? N12 C13 C14 122.4(3) . . ? N12 C13 H13 118.8 . . ? C14 C13 H13 118.8 . . ? C15 C14 C13 117.0(3) . . ? C15 C14 H14 121.5 . . ? C13 C14 H14 121.5 . . ? N16 C15 C14 122.6(3) . . ? N16 C15 H15 118.7 . . ? C14 C15 H15 118.7 . . ? C11 N16 C15 115.9(2) . . ? C18 C17 C11 179.4(3) . . ? C17 C18 C19 178.9(3) . . ? C114 C19 C110 118.2(3) . . ? C114 C19 C18 121.4(3) . . ? C110 C19 C18 120.4(3) . . ? N22 C21 N26 127.0(2) . . ? N22 C21 C27 116.6(3) . . ? N26 C21 C27 116.5(2) . . ? C21 N22 C23 115.3(3) . . ? N22 C23 C24 122.4(3) . . ? N22 C23 H23 118.8 . . ? C24 C23 H23 118.8 . . ? C25 C24 C23 117.1(3) . . ? C25 C24 H24 121.4 . . ? C23 C24 H24 121.4 . . ? N26 C25 C24 122.9(3) . . ? N26 C25 H25 118.5 . . ? C24 C25 H25 118.5 . . ? C25 N26 C21 115.2(2) . . ? C28 C27 C21 177.8(3) . . ? C27 C28 C29 177.1(3) . . ? C214 C29 C210 119.0(3) . . ? C214 C29 C28 120.4(2) . . ? C210 C29 C28 120.5(3) . . ? C111 C110 C19 120.4(3) . . ? C111 C110 H110 119.8 . . ? C19 C110 H110 119.8 . . ? C110 C111 C112 120.5(3) . . ? C110 C111 H111 119.8 . . ? C112 C111 H111 119.8 . . ? C111 C112 C113 119.5(3) . . ? C111 C112 H112 120.2 . . ? C113 C112 H112 120.2 . . ? C114 C113 C112 120.1(3) . . ? C114 C113 H113 120.0 . . ? C112 C113 H113 120.0 . . ? C113 C114 C19 121.3(3) . . ? C113 C114 H114 119.4 . . ? C19 C114 H114 119.4 . . ? C211 C210 C29 119.8(3) . . ? C211 C210 H210 120.1 . . ? C29 C210 H210 120.1 . . ? C212 C211 C210 120.5(3) . . ? C212 C211 H211 119.7 . . ? C210 C211 H211 119.7 . . ? C211 C212 C213 120.2(3) . . ? C211 C212 H212 119.9 . . ? C213 C212 H212 119.9 . . ? C214 C213 C212 119.8(3) . . ? C214 C213 H213 120.1 . . ? C212 C213 H213 120.1 . . ? C213 C214 C29 120.6(3) . . ? C213 C214 H214 119.7 . . ? C29 C214 H214 119.7 . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 26.02 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.279 _refine_diff_density_min -0.216 _refine_diff_density_rms 0.047 #===END # Attachment '- compound 25 X-ray.cif' data_mc264-et2o-teply-uochb _database_code_depnum_ccdc_archive 'CCDC 736013' #TrackingRef '- compound 25 X-ray.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H13 N2, C F3 O3 S' _chemical_formula_sum 'C17 H13 F3 N2 O3 S' _chemical_formula_weight 382.35 _chemical_compound_source 'synthesized by the authors' 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' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.4977(2) _cell_length_b 10.5242(2) _cell_length_c 11.7581(3) _cell_angle_alpha 81.4639(15) _cell_angle_beta 79.5813(13) _cell_angle_gamma 75.5501(15) _cell_volume 878.42(4) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 4011 _cell_measurement_theta_min 1 _cell_measurement_theta_max 27.5 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.446 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 392 _exptl_absorpt_coefficient_mu 0.234 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 'Nonius KappaCCD area detector' _diffrn_measurement_method '\f and \w scans to fill the Ewald sphere' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 25232 _diffrn_reflns_av_R_equivalents 0.035 _diffrn_reflns_av_sigmaI/netI 0.0226 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.77 _diffrn_reflns_theta_max 27.51 _reflns_number_total 4048 _reflns_number_gt 3457 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997)' _computing_cell_refinement 'COLLECT and DENZO' _computing_data_reduction 'COLLECT and DENZO' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _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^)+(0.0673P)^2^+0.1947P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4048 _refine_ls_number_parameters 235 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0449 _refine_ls_R_factor_gt 0.0363 _refine_ls_wR_factor_ref 0.1114 _refine_ls_wR_factor_gt 0.1032 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.037 _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 C1 C 0.74354(18) 0.05672(13) 0.13554(11) 0.0300(3) Uani 1 1 d . . . N2 N 0.75229(15) 0.02875(11) 0.25186(10) 0.0278(2) Uani 1 1 d . . . C3 C 0.66324(18) -0.05989(14) 0.31596(12) 0.0315(3) Uani 1 1 d . . . H3 H 0.6693 -0.0798 0.3969 0.038 Uiso 1 1 calc R . . C4 C 0.56328(19) -0.12165(15) 0.26368(13) 0.0349(3) Uani 1 1 d . . . H4 H 0.5020 -0.1866 0.3066 0.042 Uiso 1 1 calc R . . C5 C 0.5552(2) -0.08591(15) 0.14684(13) 0.0367(3) Uani 1 1 d . . . H5 H 0.4828 -0.1253 0.1102 0.044 Uiso 1 1 calc R . . N6 N 0.64506(17) 0.00185(13) 0.08251(11) 0.0357(3) Uani 1 1 d . . . C7 C 0.8467(2) 0.14690(15) 0.06988(12) 0.0354(3) Uani 1 1 d . . . C8 C 0.9403(2) 0.21980(14) 0.01749(12) 0.0347(3) Uani 1 1 d . . . C9 C 1.0602(2) 0.30500(14) -0.03768(12) 0.0343(3) Uani 1 1 d . . . C10 C 1.0438(2) 0.37128(16) -0.14890(13) 0.0432(4) Uani 1 1 d . . . H10 H 0.9515 0.3613 -0.1904 0.052 Uiso 1 1 calc R . . C11 C 1.1656(3) 0.45221(17) -0.19755(15) 0.0520(5) Uani 1 1 d . . . H11 H 1.1554 0.4985 -0.2727 0.062 Uiso 1 1 calc R . . C12 C 1.3007(3) 0.46590(17) -0.13784(16) 0.0522(5) Uani 1 1 d . . . H12 H 1.3832 0.5211 -0.1722 0.063 Uiso 1 1 calc R . . C13 C 1.3169(3) 0.39995(18) -0.02865(15) 0.0517(4) Uani 1 1 d . . . H13 H 1.4110 0.4091 0.0118 0.062 Uiso 1 1 calc R . . C14 C 1.1965(2) 0.32057(16) 0.02203(13) 0.0422(4) Uani 1 1 d . . . H14 H 1.2065 0.2763 0.0979 0.051 Uiso 1 1 calc R . . C15 C 0.8588(2) 0.09570(14) 0.30932(13) 0.0349(3) Uani 1 1 d . . . H15A H 0.8025 0.1009 0.3919 0.042 Uiso 1 1 calc R . . H15B H 0.8519 0.1868 0.2711 0.042 Uiso 1 1 calc R . . C16 C 1.0621(2) 0.02093(16) 0.30229(15) 0.0410(4) Uani 1 1 d . . . H16A H 1.1169 0.0133 0.2197 0.049 Uiso 1 1 calc R . . H16B H 1.1323 0.0713 0.3351 0.049 Uiso 1 1 calc R . . C17 C 1.0810(2) -0.11124(16) 0.36576(14) 0.0389(3) Uani 1 1 d . . . C18 C 1.0843(2) -0.21471(17) 0.42045(16) 0.0462(4) Uani 1 1 d . . . H18 H 1.0869 -0.2982 0.4646 0.055 Uiso 1 1 calc R . . C19 C 0.3774(3) 0.39544(17) 0.41982(15) 0.0474(4) Uani 1 1 d . . . S1 S 0.33688(5) 0.27130(3) 0.34136(3) 0.02984(12) Uani 1 1 d . . . F1 F 0.2688(2) 0.40222(14) 0.52216(11) 0.0826(4) Uani 1 1 d . . . F2 F 0.34273(19) 0.51438(10) 0.36105(11) 0.0709(4) Uani 1 1 d . . . F3 F 0.55316(18) 0.36909(13) 0.43701(12) 0.0781(4) Uani 1 1 d . . . O1 O 0.46355(15) 0.27864(10) 0.23423(8) 0.0365(2) Uani 1 1 d . . . O2 O 0.38577(15) 0.15113(10) 0.41713(9) 0.0390(3) Uani 1 1 d . . . O3 O 0.14273(15) 0.31345(12) 0.33058(10) 0.0468(3) 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 C1 0.0266(6) 0.0344(7) 0.0279(6) -0.0043(5) -0.0034(5) -0.0048(5) N2 0.0238(5) 0.0302(6) 0.0288(6) -0.0044(4) -0.0050(4) -0.0033(4) C3 0.0247(6) 0.0357(7) 0.0297(7) -0.0017(5) -0.0019(5) -0.0016(5) C4 0.0256(7) 0.0375(7) 0.0400(8) -0.0008(6) -0.0021(6) -0.0084(5) C5 0.0315(7) 0.0410(8) 0.0401(8) -0.0065(6) -0.0065(6) -0.0111(6) N6 0.0340(6) 0.0429(7) 0.0328(6) -0.0056(5) -0.0069(5) -0.0111(5) C7 0.0355(8) 0.0390(8) 0.0311(7) -0.0026(6) -0.0056(6) -0.0080(6) C8 0.0359(8) 0.0371(7) 0.0299(7) -0.0029(6) -0.0043(6) -0.0070(6) C9 0.0407(8) 0.0315(7) 0.0280(7) -0.0029(5) 0.0012(6) -0.0082(6) C10 0.0462(9) 0.0444(8) 0.0317(8) 0.0018(6) -0.0027(6) -0.0025(7) C11 0.0670(12) 0.0401(9) 0.0346(8) 0.0076(7) 0.0089(8) -0.0041(8) C12 0.0672(12) 0.0402(9) 0.0474(10) -0.0039(7) 0.0116(8) -0.0240(8) C13 0.0662(12) 0.0517(10) 0.0461(9) -0.0077(8) -0.0012(8) -0.0337(9) C14 0.0583(10) 0.0427(8) 0.0297(7) -0.0017(6) -0.0036(7) -0.0226(7) C15 0.0376(8) 0.0351(7) 0.0359(7) -0.0066(6) -0.0116(6) -0.0097(6) C16 0.0322(8) 0.0471(9) 0.0484(9) -0.0009(7) -0.0134(6) -0.0148(6) C17 0.0246(7) 0.0488(9) 0.0447(8) -0.0084(7) -0.0091(6) -0.0063(6) C18 0.0354(8) 0.0442(9) 0.0545(10) -0.0018(8) -0.0079(7) -0.0018(7) C19 0.0566(10) 0.0407(8) 0.0457(9) -0.0161(7) -0.0030(8) -0.0093(7) S1 0.0317(2) 0.02834(18) 0.02853(19) -0.00290(13) -0.00497(13) -0.00491(13) F1 0.1149(11) 0.0862(9) 0.0502(7) -0.0389(6) 0.0149(7) -0.0307(8) F2 0.0937(9) 0.0318(5) 0.0836(9) -0.0161(5) -0.0007(7) -0.0110(5) F3 0.0717(8) 0.0793(9) 0.1024(10) -0.0390(7) -0.0362(8) -0.0191(6) O1 0.0413(6) 0.0357(5) 0.0294(5) -0.0017(4) -0.0006(4) -0.0073(4) O2 0.0450(6) 0.0320(5) 0.0342(5) 0.0037(4) -0.0029(4) -0.0045(4) O3 0.0326(6) 0.0547(7) 0.0498(7) -0.0015(5) -0.0096(5) -0.0041(5) _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 C1 N6 1.3242(18) . ? C1 N2 1.3656(17) . ? C1 C7 1.424(2) . ? N2 C3 1.3432(18) . ? N2 C15 1.4858(17) . ? C3 C4 1.375(2) . ? C3 H3 0.9500 . ? C4 C5 1.378(2) . ? C4 H4 0.9500 . ? C5 N6 1.3407(19) . ? C5 H5 0.9500 . ? C7 C8 1.197(2) . ? C8 C9 1.433(2) . ? C9 C14 1.393(2) . ? C9 C10 1.399(2) . ? C10 C11 1.393(2) . ? C10 H10 0.9500 . ? C11 C12 1.379(3) . ? C11 H11 0.9500 . ? C12 C13 1.376(3) . ? C12 H12 0.9500 . ? C13 C14 1.379(2) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? C15 C16 1.525(2) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 C17 1.464(2) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 C18 1.177(2) . ? C18 H18 0.9500 . ? C19 F3 1.323(2) . ? C19 F2 1.326(2) . ? C19 F1 1.326(2) . ? C19 S1 1.8187(16) . ? S1 O3 1.4352(11) . ? S1 O1 1.4387(10) . ? S1 O2 1.4421(10) . ? 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 N6 C1 N2 122.30(13) . . ? N6 C1 C7 119.54(13) . . ? N2 C1 C7 118.15(12) . . ? C3 N2 C1 119.99(12) . . ? C3 N2 C15 119.14(11) . . ? C1 N2 C15 120.87(11) . . ? N2 C3 C4 119.54(13) . . ? N2 C3 H3 120.2 . . ? C4 C3 H3 120.2 . . ? C3 C4 C5 117.54(13) . . ? C3 C4 H4 121.2 . . ? C5 C4 H4 121.2 . . ? N6 C5 C4 122.99(14) . . ? N6 C5 H5 118.5 . . ? C4 C5 H5 118.5 . . ? C1 N6 C5 117.57(13) . . ? C8 C7 C1 176.88(16) . . ? C7 C8 C9 175.52(16) . . ? C14 C9 C10 119.97(14) . . ? C14 C9 C8 118.34(13) . . ? C10 C9 C8 121.69(15) . . ? C11 C10 C9 118.67(17) . . ? C11 C10 H10 120.7 . . ? C9 C10 H10 120.7 . . ? C12 C11 C10 120.75(16) . . ? C12 C11 H11 119.6 . . ? C10 C11 H11 119.6 . . ? C13 C12 C11 120.34(16) . . ? C13 C12 H12 119.8 . . ? C11 C12 H12 119.8 . . ? C12 C13 C14 120.03(18) . . ? C12 C13 H13 120.0 . . ? C14 C13 H13 120.0 . . ? C13 C14 C9 120.24(15) . . ? C13 C14 H14 119.9 . . ? C9 C14 H14 119.9 . . ? N2 C15 C16 110.82(12) . . ? N2 C15 H15A 109.5 . . ? C16 C15 H15A 109.5 . . ? N2 C15 H15B 109.5 . . ? C16 C15 H15B 109.5 . . ? H15A C15 H15B 108.1 . . ? C17 C16 C15 111.70(13) . . ? C17 C16 H16A 109.3 . . ? C15 C16 H16A 109.3 . . ? C17 C16 H16B 109.3 . . ? C15 C16 H16B 109.3 . . ? H16A C16 H16B 107.9 . . ? C18 C17 C16 175.53(17) . . ? C17 C18 H18 180.0 . . ? F3 C19 F2 106.84(15) . . ? F3 C19 F1 108.63(15) . . ? F2 C19 F1 107.46(14) . . ? F3 C19 S1 111.08(11) . . ? F2 C19 S1 111.53(12) . . ? F1 C19 S1 111.11(13) . . ? O3 S1 O1 115.41(7) . . ? O3 S1 O2 114.80(7) . . ? O1 S1 O2 114.13(6) . . ? O3 S1 C19 104.07(8) . . ? O1 S1 C19 103.29(7) . . ? O2 S1 C19 102.90(7) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.51 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.239 _refine_diff_density_min -0.397 _refine_diff_density_rms 0.043 #===END