# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2004 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Paul Seiler' _publ_contact_author_email seiler@org.chem.ethz.ch loop_ _publ_author_name '.A. Olsen' 'P. Seiler' B.Wagner 'T. Tschopp' 'U. Obst-Sander' 'D.W. Banner' 'M. Kansy' 'K. Muller' 'F. Diederich' data_olsen3 _database_code_depnum_ccdc_archive 'CCDC 231343' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety 'C23 H19 F2 N3 O2' _chemical_formula_sum 'C23 H19 F2 N3 O2' _chemical_formula_weight 407.41 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.673(1) _cell_length_b 11.394(2) _cell_length_c 11.894(2) _cell_angle_alpha 97.22(1) _cell_angle_beta 106.92(1) _cell_angle_gamma 90.85(1) _cell_volume 985.5(3) _cell_formula_units_Z 2 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 18 _cell_measurement_theta_min 18.60 _cell_measurement_theta_max 24.40 _exptl_crystal_description 'Cut fragment' _exptl_crystal_colour colorless _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.373 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 424 _exptl_absorpt_coefficient_mu 0.853 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.8345 _exptl_absorpt_correction_T_max 0.8616 _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(2) _diffrn_radiation_wavelength 1.54180 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'NONIUS CAD4' _diffrn_measurement_method \q/\q _diffrn_detector_area_resol_mean ? _diffrn_standards_number 2 _diffrn_standards_interval_count ? _diffrn_standards_interval_time '167 min.' _diffrn_standards_decay_% 0.200 _diffrn_reflns_number 4111 _diffrn_reflns_av_R_equivalents 0.030 _diffrn_reflns_av_sigmaI/netI 0.0197 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.92 _diffrn_reflns_theta_max 74.90 _reflns_number_total 3904 _reflns_number_gt 3272 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CAD4 VMS-software (Nonius, 1989)' _computing_cell_refinement 'CAD4 VMS-software (Nonius, 1989)' _computing_data_reduction 'MOLEN VMS-software (Nonius, 1990)' _computing_structure_solution 'SIR92 (Altomare et al.,1994)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP (Johnson,1976)' _computing_publication_material SHELXL97 _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 'w=1/[\s^2^(Fo^2^)+(0.0569P)^2^+0.2816P] 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 'H-atoms riding' _refine_ls_extinction_method SHELXL97 _refine_ls_extinction_coef 0.0050(7) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3904 _refine_ls_number_parameters 291 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0533 _refine_ls_R_factor_gt 0.0449 _refine_ls_wR_factor_ref 0.1343 _refine_ls_wR_factor_gt 0.1256 _refine_ls_goodness_of_fit_ref 1.080 _refine_ls_restrained_S_all 1.080 _refine_ls_shift/su_max 0.004 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.7394(2) 0.36009(17) 0.96883(16) 0.0610(5) Uani 1 d . . . N2 N 0.74261(18) 0.35181(13) 0.85262(13) 0.0553(4) Uani 1 d . . . C3 C 0.6798(2) 0.24175(15) 0.78805(15) 0.0530(4) Uani 1 d . . . C4 C 0.6164(2) 0.16642(15) 0.86572(15) 0.0524(4) Uani 1 d . . . H4A H 0.6811 0.0919 0.8726 0.063(5) Uiso 1 calc R . . C5 C 0.6575(2) 0.24508(16) 0.98676(15) 0.0573(4) Uani 1 d . . . H5A H 0.7401 0.2081 1.0516 0.075(6) Uiso 1 calc R . . O6 O 0.7903(2) 0.44793(14) 1.04118(13) 0.0840(5) Uani 1 d . . . O7 O 0.67845(18) 0.21599(12) 0.68626(12) 0.0672(4) Uani 1 d . . . C8 C 0.7985(2) 0.44880(18) 0.79999(19) 0.0668(5) Uani 1 d . . . H8A H 0.8692 0.4176 0.7473 0.090(7) Uiso 1 calc R . . H8B H 0.8784 0.5059 0.8632 0.090(7) Uiso 1 calc R . . C9 C 0.6402(2) 0.51236(15) 0.73025(16) 0.0565(4) Uani 1 d . . . C10 C 0.4659(2) 0.49831(17) 0.74034(18) 0.0624(5) Uani 1 d . . . H10A H 0.4438 0.4492 0.7932 0.069(6) Uiso 1 calc R . . C11 C 0.3249(3) 0.5563(2) 0.6730(2) 0.0789(6) Uani 1 d . . . H11A H 0.2064 0.5472 0.6796 0.095(8) Uiso 1 calc R . . C12 C 0.3593(3) 0.6271(2) 0.5966(2) 0.0834(7) Uani 1 d . . . C13 C 0.5282(3) 0.6452(2) 0.5857(2) 0.0814(6) Uani 1 d . . . H13A H 0.5487 0.6956 0.5335 0.111(9) Uiso 1 calc R . . C14 C 0.6684(3) 0.58743(18) 0.6533(2) 0.0705(5) Uani 1 d . . . H14A H 0.7867 0.5991 0.6472 0.103(8) Uiso 1 calc R . . F15 F 0.2189(2) 0.68030(18) 0.52778(19) 0.1350(7) Uani 1 d . . . C16 C 0.4060(2) 0.14205(14) 0.82495(14) 0.0489(4) Uani 1 d . . . H16A H 0.3762 0.0708 0.8570 0.055(5) Uiso 1 calc R . . N17 N 0.34423(18) 0.24710(11) 0.88525(12) 0.0487(3) Uani 1 d . . . C18 C 0.1648(2) 0.22777(18) 0.90441(18) 0.0645(5) Uani 1 d . . . H18A H 0.0841 0.1757 0.8369 0.067(6) Uiso 1 calc R . . H18B H 0.1075 0.3034 0.9125 0.080(6) Uiso 1 calc R . . C19 C 0.1960(3) 0.1709(3) 1.0173(2) 0.0915(8) Uani 1 d . . . H19A H 0.1519 0.0875 0.9986 0.166(15) Uiso 1 calc R . . H19B H 0.1322 0.2124 1.0696 0.148(13) Uiso 1 calc R . . C20 C 0.4021(3) 0.18185(19) 1.07610(18) 0.0721(5) Uani 1 d . . . H20A H 0.4556 0.1046 1.0699 0.100(8) Uiso 1 calc R . . H20B H 0.4313 0.2149 1.1600 0.080(6) Uiso 1 calc R . . C21 C 0.4709(2) 0.26621(15) 1.00594(15) 0.0544(4) Uani 1 d . . . H21A H 0.4684 0.3492 1.0418 0.063(5) Uiso 1 calc R . . C22 C 0.3176(2) 0.12593(14) 0.69254(14) 0.0487(4) Uani 1 d . . . C23 C 0.2114(2) 0.20964(16) 0.63399(16) 0.0556(4) Uani 1 d . . . H23A H 0.1915 0.2800 0.6780 0.061(5) Uiso 1 calc R . . C24 C 0.1341(2) 0.19204(18) 0.51231(17) 0.0619(5) Uani 1 d . . . H24A H 0.0634 0.2502 0.4740 0.078(7) Uiso 1 calc R . . C25 C 0.1616(2) 0.08758(18) 0.44675(16) 0.0605(5) Uani 1 d . . . C26 C 0.2657(3) 0.00209(17) 0.50210(17) 0.0632(5) Uani 1 d . . . H26A H 0.2849 -0.0687 0.4585 0.092(7) Uiso 1 calc R . . C27 C 0.3401(3) 0.02360(15) 0.62264(16) 0.0564(4) Uani 1 d . . . F28 F 0.44564(19) -0.05853(10) 0.67760(11) 0.0824(4) Uani 1 d . . . C29 C 0.0775(3) 0.0713(2) 0.31993(19) 0.0775(6) Uani 1 d . . . N30 N 0.0072(3) 0.0617(2) 0.22035(18) 0.1077(8) Uani 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 0.0444(8) 0.0730(11) 0.0569(10) -0.0078(9) 0.0087(7) 0.0000(8) N2 0.0437(7) 0.0593(8) 0.0586(8) -0.0011(6) 0.0123(6) -0.0002(6) C3 0.0415(8) 0.0577(9) 0.0572(9) -0.0027(7) 0.0149(7) 0.0083(7) C4 0.0516(9) 0.0497(9) 0.0550(9) 0.0035(7) 0.0151(7) 0.0151(7) C5 0.0541(9) 0.0638(10) 0.0493(9) 0.0045(8) 0.0089(7) 0.0115(8) O6 0.0742(9) 0.0917(10) 0.0740(9) -0.0266(8) 0.0201(7) -0.0265(8) O7 0.0688(8) 0.0739(8) 0.0615(8) -0.0071(6) 0.0303(6) -0.0008(6) C8 0.0482(9) 0.0710(12) 0.0772(13) 0.0016(10) 0.0163(9) -0.0096(8) C9 0.0557(9) 0.0490(9) 0.0628(10) -0.0074(7) 0.0210(8) -0.0044(7) C10 0.0598(10) 0.0602(10) 0.0726(12) 0.0055(9) 0.0292(9) 0.0059(8) C11 0.0639(12) 0.0825(14) 0.1046(17) 0.0226(13) 0.0420(12) 0.0219(10) C12 0.0825(14) 0.0823(15) 0.0995(17) 0.0302(13) 0.0398(13) 0.0320(12) C13 0.0909(15) 0.0715(13) 0.0970(16) 0.0214(12) 0.0468(13) 0.0138(11) C14 0.0686(12) 0.0638(11) 0.0857(14) 0.0056(10) 0.0353(10) -0.0024(9) F15 0.1069(12) 0.1619(16) 0.1744(17) 0.0992(14) 0.0658(11) 0.0715(11) C16 0.0538(8) 0.0413(8) 0.0535(9) 0.0018(7) 0.0205(7) 0.0057(6) N17 0.0481(7) 0.0467(7) 0.0520(7) -0.0027(6) 0.0197(6) 0.0046(5) C18 0.0557(10) 0.0692(11) 0.0723(12) -0.0063(9) 0.0318(9) -0.0026(8) C19 0.0920(16) 0.115(2) 0.0750(14) 0.0065(13) 0.0397(13) -0.0235(15) C20 0.0976(15) 0.0670(12) 0.0579(11) 0.0071(9) 0.0334(10) 0.0035(11) C21 0.0615(10) 0.0512(9) 0.0502(9) -0.0005(7) 0.0193(7) 0.0051(7) C22 0.0484(8) 0.0461(8) 0.0532(9) -0.0006(7) 0.0209(7) -0.0009(6) C23 0.0523(9) 0.0540(9) 0.0596(10) 0.0002(8) 0.0180(7) 0.0057(7) C24 0.0509(9) 0.0710(12) 0.0623(10) 0.0097(9) 0.0139(8) 0.0002(8) C25 0.0562(9) 0.0713(11) 0.0533(9) -0.0020(8) 0.0204(8) -0.0188(8) C26 0.0749(12) 0.0572(10) 0.0606(10) -0.0083(8) 0.0324(9) -0.0094(9) C27 0.0648(10) 0.0468(9) 0.0604(10) 0.0008(7) 0.0256(8) 0.0046(7) F28 0.1168(10) 0.0557(6) 0.0749(8) -0.0005(5) 0.0315(7) 0.0289(6) C29 0.0816(13) 0.0894(15) 0.0590(12) 0.0017(10) 0.0223(10) -0.0321(11) N30 0.1289(19) 0.1252(18) 0.0570(11) 0.0031(11) 0.0155(11) -0.0532(15) _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 O6 1.213(2) . ? C1 N2 1.381(2) . ? C1 C5 1.511(3) . ? N2 C3 1.385(2) . ? N2 C8 1.454(2) . ? C3 O7 1.206(2) . ? C3 C4 1.509(3) . ? C4 C5 1.542(2) . ? C4 C16 1.554(2) . ? C5 C21 1.531(2) . ? C8 C9 1.510(3) . ? C9 C10 1.386(2) . ? C9 C14 1.387(3) . ? C10 C11 1.377(3) . ? C11 C12 1.365(3) . ? C12 C13 1.355(3) . ? C12 F15 1.353(3) . ? C13 C14 1.374(3) . ? C16 N17 1.4734(19) . ? C16 C22 1.509(2) . ? N17 C21 1.468(2) . ? N17 C18 1.477(2) . ? C18 C19 1.521(3) . ? C19 C20 1.528(3) . ? C20 C21 1.531(3) . ? C22 C23 1.385(2) . ? C22 C27 1.388(2) . ? C23 C24 1.382(3) . ? C24 C25 1.392(3) . ? C25 C26 1.378(3) . ? C25 C29 1.444(3) . ? C26 C27 1.368(3) . ? C27 F28 1.352(2) . ? C29 N30 1.140(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O6 C1 N2 124.11(19) . . ? O6 C1 C5 127.22(18) . . ? N2 C1 C5 108.63(15) . . ? C1 N2 C3 113.16(16) . . ? C1 N2 C8 124.36(15) . . ? C3 N2 C8 122.43(15) . . ? O7 C3 N2 122.96(17) . . ? O7 C3 C4 128.34(16) . . ? N2 C3 C4 108.69(14) . . ? C3 C4 C5 104.64(14) . . ? C3 C4 C16 112.54(14) . . ? C5 C4 C16 104.69(13) . . ? C1 C5 C21 109.42(15) . . ? C1 C5 C4 104.78(14) . . ? C21 C5 C4 105.22(13) . . ? N2 C8 C9 113.32(14) . . ? C10 C9 C14 118.41(18) . . ? C10 C9 C8 122.13(17) . . ? C14 C9 C8 119.46(17) . . ? C11 C10 C9 120.03(19) . . ? C12 C11 C10 119.2(2) . . ? C13 C12 F15 118.5(2) . . ? C13 C12 C11 122.7(2) . . ? F15 C12 C11 118.8(2) . . ? C12 C13 C14 117.8(2) . . ? C13 C14 C9 121.79(19) . . ? N17 C16 C22 112.17(13) . . ? N17 C16 C4 102.10(12) . . ? C22 C16 C4 115.29(13) . . ? C21 N17 C16 105.36(12) . . ? C21 N17 C18 103.53(13) . . ? C16 N17 C18 113.85(13) . . ? N17 C18 C19 107.72(17) . . ? C18 C19 C20 105.51(17) . . ? C19 C20 C21 103.67(17) . . ? N17 C21 C5 103.54(13) . . ? N17 C21 C20 106.16(15) . . ? C5 C21 C20 117.49(16) . . ? C23 C22 C27 116.41(16) . . ? C23 C22 C16 123.19(14) . . ? C27 C22 C16 120.40(15) . . ? C24 C23 C22 121.44(16) . . ? C23 C24 C25 119.59(18) . . ? C26 C25 C24 120.56(17) . . ? C26 C25 C29 121.18(19) . . ? C24 C25 C29 118.3(2) . . ? C27 C26 C25 117.80(17) . . ? F28 C27 C26 118.32(16) . . ? F28 C27 C22 117.46(16) . . ? C26 C27 C22 124.21(18) . . ? N30 C29 C25 177.6(3) . . ? 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 O6 C1 N2 C3 179.13(17) . . . . ? C5 C1 N2 C3 -2.82(19) . . . . ? O6 C1 N2 C8 -3.2(3) . . . . ? C5 C1 N2 C8 174.80(15) . . . . ? C1 N2 C3 O7 -177.20(15) . . . . ? C8 N2 C3 O7 5.1(2) . . . . ? C1 N2 C3 C4 3.25(18) . . . . ? C8 N2 C3 C4 -174.42(14) . . . . ? O7 C3 C4 C5 178.23(17) . . . . ? N2 C3 C4 C5 -2.25(17) . . . . ? O7 C3 C4 C16 -68.7(2) . . . . ? N2 C3 C4 C16 110.84(14) . . . . ? O6 C1 C5 C21 66.8(2) . . . . ? N2 C1 C5 C21 -111.20(15) . . . . ? O6 C1 C5 C4 179.17(18) . . . . ? N2 C1 C5 C4 1.20(18) . . . . ? C3 C4 C5 C1 0.63(16) . . . . ? C16 C4 C5 C1 -117.94(14) . . . . ? C3 C4 C5 C21 115.98(14) . . . . ? C16 C4 C5 C21 -2.58(18) . . . . ? C1 N2 C8 C9 -97.79(19) . . . . ? C3 N2 C8 C9 79.6(2) . . . . ? N2 C8 C9 C10 14.8(2) . . . . ? N2 C8 C9 C14 -165.12(17) . . . . ? C14 C9 C10 C11 1.3(3) . . . . ? C8 C9 C10 C11 -178.64(18) . . . . ? C9 C10 C11 C12 0.1(3) . . . . ? C10 C11 C12 C13 -1.4(4) . . . . ? C10 C11 C12 F15 177.7(2) . . . . ? F15 C12 C13 C14 -177.9(2) . . . . ? C11 C12 C13 C14 1.3(4) . . . . ? C12 C13 C14 C9 0.3(3) . . . . ? C10 C9 C14 C13 -1.5(3) . . . . ? C8 C9 C14 C13 178.43(19) . . . . ? C3 C4 C16 N17 -85.93(15) . . . . ? C5 C4 C16 N17 27.13(16) . . . . ? C3 C4 C16 C22 35.95(18) . . . . ? C5 C4 C16 C22 149.01(14) . . . . ? C22 C16 N17 C21 -167.19(13) . . . . ? C4 C16 N17 C21 -43.20(16) . . . . ? C22 C16 N17 C18 80.06(17) . . . . ? C4 C16 N17 C18 -155.95(14) . . . . ? C21 N17 C18 C19 -30.3(2) . . . . ? C16 N17 C18 C19 83.56(19) . . . . ? N17 C18 C19 C20 11.5(2) . . . . ? C18 C19 C20 C21 11.0(2) . . . . ? C16 N17 C21 C5 42.00(16) . . . . ? C18 N17 C21 C5 161.83(14) . . . . ? C16 N17 C21 C20 -82.34(16) . . . . ? C18 N17 C21 C20 37.49(17) . . . . ? C1 C5 C21 N17 88.98(16) . . . . ? C4 C5 C21 N17 -23.12(17) . . . . ? C1 C5 C21 C20 -154.40(16) . . . . ? C4 C5 C21 C20 93.50(18) . . . . ? C19 C20 C21 N17 -30.2(2) . . . . ? C19 C20 C21 C5 -145.39(18) . . . . ? N17 C16 C22 C23 8.6(2) . . . . ? C4 C16 C22 C23 -107.71(17) . . . . ? N17 C16 C22 C27 -171.43(14) . . . . ? C4 C16 C22 C27 72.28(19) . . . . ? C27 C22 C23 C24 -0.6(2) . . . . ? C16 C22 C23 C24 179.36(15) . . . . ? C22 C23 C24 C25 0.6(3) . . . . ? C23 C24 C25 C26 -0.3(3) . . . . ? C23 C24 C25 C29 179.39(16) . . . . ? C24 C25 C26 C27 0.0(3) . . . . ? C29 C25 C26 C27 -179.66(17) . . . . ? C25 C26 C27 F28 -178.63(16) . . . . ? C25 C26 C27 C22 -0.1(3) . . . . ? C23 C22 C27 F28 178.94(15) . . . . ? C16 C22 C27 F28 -1.1(2) . . . . ? C23 C22 C27 C26 0.4(3) . . . . ? C16 C22 C27 C26 -179.64(16) . . . . ? C26 C25 C29 N30 164(5) . . . . ? C24 C25 C29 N30 -15(5) . . . . ? _diffrn_measured_fraction_theta_max 0.963 _diffrn_reflns_theta_full 74.90 _diffrn_measured_fraction_theta_full 0.963 _refine_diff_density_max 0.238 _refine_diff_density_min -0.266 _refine_diff_density_rms 0.035 data_olsen7 _database_code_depnum_ccdc_archive 'CCDC 231344' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety 'C23 H19 F2 N3 O2' _chemical_formula_sum 'C23 H19 F2 N3 O2' _chemical_formula_weight 407.41 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' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.4926(2) _cell_length_b 10.3004(3) _cell_length_c 10.9831(3) _cell_angle_alpha 93.680(1) _cell_angle_beta 94.130(1) _cell_angle_gamma 115.220(1) _cell_volume 963.64(4) _cell_formula_units_Z 2 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 4273 _cell_measurement_theta_min 1.87 _cell_measurement_theta_max 27.49 _exptl_crystal_description 'Cut fragment' _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.404 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 424 _exptl_absorpt_coefficient_mu 0.104 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9693 _exptl_absorpt_correction_T_max 0.9744 _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Kappa CCD' _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_reflns_number 8020 _diffrn_reflns_av_R_equivalents 0.0223 _diffrn_reflns_av_sigmaI/netI 0.0375 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.87 _diffrn_reflns_theta_max 27.49 _reflns_number_total 4404 _reflns_number_gt 3458 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Kappa CCD' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'Denzo + Scalepak (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR92 (Altomare et al.,1994)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP (Johnson,1976)' _computing_publication_material SHELXL97 _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 'w=1/[\s^2^(Fo^2^)+(0.0656P)^2^+0.1529P] 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 'H-atoms riding' _refine_ls_extinction_method SHELXL97 _refine_ls_extinction_coef 0.059(8) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4404 _refine_ls_number_parameters 291 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0583 _refine_ls_R_factor_gt 0.0437 _refine_ls_wR_factor_ref 0.1293 _refine_ls_wR_factor_gt 0.1161 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.048 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.55094(17) 0.49647(16) 0.28585(14) 0.0441(3) Uani 1 d . . . N2 N 0.53867(13) 0.39606(12) 0.36816(10) 0.0386(3) Uani 1 d . . . C3 C 0.39128(16) 0.32973(14) 0.40580(11) 0.0362(3) Uani 1 d . . . C4 C 0.28336(16) 0.37654(14) 0.33149(12) 0.0359(3) Uani 1 d . . . H4A H 0.2237 0.4104 0.3851 0.041(4) Uiso 1 calc R . . C5 C 0.39321(17) 0.49887(15) 0.26242(13) 0.0401(3) Uani 1 d . . . H5A H 0.3971 0.5934 0.2918 0.050(5) Uiso 1 calc R . . O6 O 0.66969(13) 0.56698(14) 0.24192(13) 0.0646(4) Uani 1 d . . . O7 O 0.35890(12) 0.24896(12) 0.48535(9) 0.0477(3) Uani 1 d . . . C8 C 0.66795(17) 0.36058(17) 0.40802(14) 0.0444(3) Uani 1 d . . . H8A H 0.6633 0.3415 0.4943 0.059(5) Uiso 1 calc R . . H8B H 0.7679 0.4435 0.4019 0.052(5) Uiso 1 calc R . . C9 C 0.66103(15) 0.23086(16) 0.33167(13) 0.0405(3) Uani 1 d . . . C10 C 0.6767(2) 0.2341(2) 0.20692(15) 0.0547(4) Uani 1 d . . . H10A H 0.6967 0.3197 0.1709 0.075(6) Uiso 1 calc R . . C11 C 0.6633(2) 0.1139(2) 0.13538(17) 0.0651(5) Uani 1 d . . . H11A H 0.6733 0.1165 0.0509 0.079(7) Uiso 1 calc R . . C12 C 0.6352(2) -0.0092(2) 0.18938(19) 0.0619(5) Uani 1 d . . . C13 C 0.62320(19) -0.01663(19) 0.31271(19) 0.0578(4) Uani 1 d . . . H13A H 0.6070 -0.1018 0.3483 0.070(6) Uiso 1 calc R . . C14 C 0.63551(17) 0.10466(18) 0.38319(15) 0.0471(4) Uani 1 d . . . H14A H 0.6264 0.1013 0.4677 0.059(5) Uiso 1 calc R . . F15 F 0.61762(18) -0.12905(16) 0.11861(15) 0.0988(5) Uani 1 d . . . C16 C 0.17185(15) 0.25819(14) 0.22770(12) 0.0348(3) Uani 1 d . . . H16A H 0.0725 0.2677 0.2151 0.043(4) Uiso 1 calc R . . N17 N 0.25438(14) 0.29702(12) 0.11781(10) 0.0374(3) Uani 1 d . . . C18 C 0.1459(2) 0.25423(18) 0.00385(13) 0.0494(4) Uani 1 d . . . H18A H 0.0565 0.1613 0.0086 0.053(5) Uiso 1 calc R . . H18B H 0.1996 0.2452 -0.0669 0.070(6) Uiso 1 calc R . . C19 C 0.0904(2) 0.3730(2) -0.00899(15) 0.0550(4) Uani 1 d . . . H19A H 0.0938 0.3993 -0.0933 0.063(5) Uiso 1 calc R . . H19B H -0.0171 0.3405 0.0122 0.076(6) Uiso 1 calc R . . C20 C 0.2034(2) 0.50114(18) 0.08023(15) 0.0510(4) Uani 1 d . . . H20A H 0.1502 0.5190 0.1481 0.072(6) Uiso 1 calc R . . H20B H 0.2488 0.5887 0.0384 0.070(6) Uiso 1 calc R . . C21 C 0.33020(18) 0.45554(15) 0.12689(13) 0.0405(3) Uani 1 d . . . H21A H 0.4177 0.4891 0.0752 0.043(4) Uiso 1 calc R . . C22 C 0.13502(14) 0.10523(14) 0.25249(11) 0.0338(3) Uani 1 d . . . C23 C 0.22422(15) 0.03850(14) 0.20814(13) 0.0367(3) Uani 1 d . . . H23A H 0.3044 0.0860 0.1592 0.043(4) Uiso 1 calc R . . C24 C 0.19275(15) -0.09789(15) 0.23728(13) 0.0372(3) Uani 1 d . . . C25 C 0.07604(15) -0.17286(15) 0.30977(12) 0.0372(3) Uani 1 d . . . C26 C -0.01569(16) -0.10693(16) 0.35090(13) 0.0431(3) Uani 1 d . . . H26A H -0.0975 -0.1557 0.3981 0.047(4) Uiso 1 calc R . . C27 C 0.01411(16) 0.03021(16) 0.32197(13) 0.0411(3) Uani 1 d . . . H27A H -0.0484 0.0739 0.3497 0.047(4) Uiso 1 calc R . . C28 C 0.05655(16) -0.31282(17) 0.33910(13) 0.0428(3) Uani 1 d . . . N29 N 0.04784(16) -0.42330(16) 0.36139(14) 0.0548(4) Uani 1 d . . . F30 F 0.27671(10) -0.16476(9) 0.19384(10) 0.0542(3) Uani 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 0.0418(8) 0.0374(7) 0.0457(8) 0.0064(6) 0.0013(6) 0.0103(6) N2 0.0351(6) 0.0381(6) 0.0376(6) 0.0042(5) -0.0008(5) 0.0119(5) C3 0.0386(7) 0.0344(7) 0.0287(6) -0.0028(5) -0.0021(5) 0.0111(5) C4 0.0389(7) 0.0367(7) 0.0319(6) -0.0018(5) 0.0014(5) 0.0172(6) C5 0.0461(8) 0.0339(7) 0.0390(7) 0.0021(6) 0.0000(6) 0.0170(6) O6 0.0459(6) 0.0612(8) 0.0782(9) 0.0305(7) 0.0114(6) 0.0111(6) O7 0.0465(6) 0.0545(6) 0.0354(5) 0.0120(5) 0.0009(4) 0.0151(5) C8 0.0356(7) 0.0489(8) 0.0428(8) 0.0031(6) -0.0049(6) 0.0145(6) C9 0.0290(6) 0.0489(8) 0.0420(7) 0.0089(6) 0.0014(5) 0.0152(6) C10 0.0623(10) 0.0601(10) 0.0457(9) 0.0147(8) 0.0142(7) 0.0277(8) C11 0.0707(12) 0.0844(14) 0.0491(10) 0.0044(9) 0.0146(8) 0.0413(10) C12 0.0532(10) 0.0654(11) 0.0751(12) -0.0086(9) 0.0029(9) 0.0361(9) C13 0.0464(9) 0.0522(10) 0.0791(12) 0.0143(9) 0.0008(8) 0.0255(7) C14 0.0374(7) 0.0547(9) 0.0491(8) 0.0153(7) 0.0019(6) 0.0190(7) F15 0.1075(10) 0.0893(9) 0.1168(11) -0.0267(8) 0.0034(8) 0.0652(8) C16 0.0324(6) 0.0393(7) 0.0333(6) -0.0027(5) -0.0011(5) 0.0178(5) N17 0.0450(6) 0.0404(6) 0.0299(5) 0.0013(5) 0.0014(5) 0.0223(5) C18 0.0637(10) 0.0551(9) 0.0333(7) -0.0043(6) -0.0072(7) 0.0324(8) C19 0.0623(10) 0.0643(10) 0.0460(8) 0.0031(8) -0.0073(7) 0.0371(8) C20 0.0688(10) 0.0548(9) 0.0425(8) 0.0066(7) -0.0010(7) 0.0399(8) C21 0.0484(8) 0.0410(7) 0.0360(7) 0.0057(6) 0.0047(6) 0.0228(6) C22 0.0303(6) 0.0359(7) 0.0321(6) -0.0030(5) -0.0026(5) 0.0133(5) C23 0.0306(6) 0.0355(7) 0.0411(7) 0.0017(5) 0.0061(5) 0.0114(5) C24 0.0307(6) 0.0361(7) 0.0420(7) -0.0005(6) 0.0017(5) 0.0128(5) C25 0.0326(6) 0.0371(7) 0.0334(6) 0.0018(5) -0.0029(5) 0.0081(5) C26 0.0362(7) 0.0469(8) 0.0387(7) 0.0033(6) 0.0078(6) 0.0105(6) C27 0.0322(7) 0.0473(8) 0.0415(7) -0.0025(6) 0.0052(5) 0.0159(6) C28 0.0351(7) 0.0465(8) 0.0388(7) 0.0071(6) -0.0019(6) 0.0106(6) N29 0.0500(8) 0.0515(8) 0.0593(8) 0.0190(7) 0.0024(6) 0.0172(6) F30 0.0474(5) 0.0412(5) 0.0806(7) 0.0085(4) 0.0212(5) 0.0230(4) _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 O6 1.2069(19) . ? C1 N2 1.3903(19) . ? C1 C5 1.512(2) . ? N2 C3 1.3785(18) . ? N2 C8 1.4686(18) . ? C3 O7 1.2099(17) . ? C3 C4 1.5163(19) . ? C4 C5 1.539(2) . ? C4 C16 1.5665(18) . ? C5 C21 1.5270(19) . ? C8 C9 1.505(2) . ? C9 C14 1.384(2) . ? C9 C10 1.390(2) . ? C10 C11 1.376(3) . ? C11 C12 1.365(3) . ? C12 F15 1.356(2) . ? C12 C13 1.372(3) . ? C13 C14 1.383(2) . ? C16 N17 1.4702(17) . ? C16 C22 1.5093(19) . ? N17 C21 1.4702(18) . ? N17 C18 1.4758(18) . ? C18 C19 1.535(2) . ? C19 C20 1.526(2) . ? C20 C21 1.534(2) . ? C22 C23 1.3925(19) . ? C22 C27 1.3939(19) . ? C23 C24 1.3708(19) . ? C24 F30 1.3483(16) . ? C24 C25 1.3908(19) . ? C25 C26 1.394(2) . ? C25 C28 1.434(2) . ? C26 C27 1.381(2) . ? C28 N29 1.149(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O6 C1 N2 123.97(15) . . ? O6 C1 C5 127.57(14) . . ? N2 C1 C5 108.46(12) . . ? C3 N2 C1 113.19(12) . . ? C3 N2 C8 123.27(12) . . ? C1 N2 C8 123.52(12) . . ? O7 C3 N2 123.96(13) . . ? O7 C3 C4 127.77(13) . . ? N2 C3 C4 108.27(11) . . ? C3 C4 C5 104.63(11) . . ? C3 C4 C16 113.24(11) . . ? C5 C4 C16 104.53(10) . . ? C1 C5 C21 110.60(12) . . ? C1 C5 C4 104.50(11) . . ? C21 C5 C4 105.81(11) . . ? N2 C8 C9 111.86(11) . . ? C14 C9 C10 118.39(16) . . ? C14 C9 C8 120.93(14) . . ? C10 C9 C8 120.66(14) . . ? C11 C10 C9 121.02(17) . . ? C12 C11 C10 118.72(17) . . ? F15 C12 C11 118.90(19) . . ? F15 C12 C13 118.66(19) . . ? C11 C12 C13 122.44(18) . . ? C12 C13 C14 118.15(17) . . ? C13 C14 C9 121.25(15) . . ? N17 C16 C22 111.74(11) . . ? N17 C16 C4 103.90(10) . . ? C22 C16 C4 114.66(11) . . ? C21 N17 C16 106.39(10) . . ? C21 N17 C18 104.07(11) . . ? C16 N17 C18 112.48(11) . . ? N17 C18 C19 106.79(12) . . ? C20 C19 C18 105.62(12) . . ? C19 C20 C21 104.18(12) . . ? N17 C21 C5 103.24(11) . . ? N17 C21 C20 106.19(12) . . ? C5 C21 C20 116.43(13) . . ? C23 C22 C27 119.21(13) . . ? C23 C22 C16 120.11(11) . . ? C27 C22 C16 120.67(12) . . ? C24 C23 C22 118.69(12) . . ? F30 C24 C23 119.45(12) . . ? F30 C24 C25 117.51(12) . . ? C23 C24 C25 123.04(13) . . ? C24 C25 C26 117.90(13) . . ? C24 C25 C28 118.74(13) . . ? C26 C25 C28 123.35(13) . . ? C27 C26 C25 119.75(13) . . ? C26 C27 C22 121.36(13) . . ? N29 C28 C25 176.86(16) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O6 C1 N2 C3 179.72(15) . . . . ? C5 C1 N2 C3 -0.76(17) . . . . ? O6 C1 N2 C8 -2.2(2) . . . . ? C5 C1 N2 C8 177.36(12) . . . . ? C1 N2 C3 O7 -172.98(13) . . . . ? C8 N2 C3 O7 8.9(2) . . . . ? C1 N2 C3 C4 6.80(15) . . . . ? C8 N2 C3 C4 -171.32(12) . . . . ? O7 C3 C4 C5 170.04(14) . . . . ? N2 C3 C4 C5 -9.73(14) . . . . ? O7 C3 C4 C16 -76.74(17) . . . . ? N2 C3 C4 C16 103.49(12) . . . . ? O6 C1 C5 C21 60.6(2) . . . . ? N2 C1 C5 C21 -118.87(13) . . . . ? O6 C1 C5 C4 174.09(16) . . . . ? N2 C1 C5 C4 -5.41(15) . . . . ? C3 C4 C5 C1 8.92(14) . . . . ? C16 C4 C5 C1 -110.35(12) . . . . ? C3 C4 C5 C21 125.73(12) . . . . ? C16 C4 C5 C21 6.47(14) . . . . ? C3 N2 C8 C9 83.49(16) . . . . ? C1 N2 C8 C9 -94.43(16) . . . . ? N2 C8 C9 C14 -115.09(14) . . . . ? N2 C8 C9 C10 63.46(18) . . . . ? C14 C9 C10 C11 1.6(2) . . . . ? C8 C9 C10 C11 -176.97(15) . . . . ? C9 C10 C11 C12 -0.4(3) . . . . ? C10 C11 C12 F15 178.18(16) . . . . ? C10 C11 C12 C13 -1.4(3) . . . . ? F15 C12 C13 C14 -177.61(14) . . . . ? C11 C12 C13 C14 2.0(3) . . . . ? C12 C13 C14 C9 -0.7(2) . . . . ? C10 C9 C14 C13 -1.0(2) . . . . ? C8 C9 C14 C13 177.56(13) . . . . ? C3 C4 C16 N17 -95.57(13) . . . . ? C5 C4 C16 N17 17.71(13) . . . . ? C3 C4 C16 C22 26.67(16) . . . . ? C5 C4 C16 C22 139.95(12) . . . . ? C22 C16 N17 C21 -160.93(10) . . . . ? C4 C16 N17 C21 -36.78(13) . . . . ? C22 C16 N17 C18 85.74(13) . . . . ? C4 C16 N17 C18 -150.11(11) . . . . ? C21 N17 C18 C19 -32.24(16) . . . . ? C16 N17 C18 C19 82.50(16) . . . . ? N17 C18 C19 C20 15.13(18) . . . . ? C18 C19 C20 C21 7.16(18) . . . . ? C16 N17 C21 C5 41.05(14) . . . . ? C18 N17 C21 C5 160.03(12) . . . . ? C16 N17 C21 C20 -81.93(13) . . . . ? C18 N17 C21 C20 37.05(14) . . . . ? C1 C5 C21 N17 84.29(13) . . . . ? C4 C5 C21 N17 -28.32(14) . . . . ? C1 C5 C21 C20 -159.81(13) . . . . ? C4 C5 C21 C20 87.57(15) . . . . ? C19 C20 C21 N17 -27.27(16) . . . . ? C19 C20 C21 C5 -141.51(14) . . . . ? N17 C16 C22 C23 24.07(16) . . . . ? C4 C16 C22 C23 -93.82(14) . . . . ? N17 C16 C22 C27 -157.34(12) . . . . ? C4 C16 C22 C27 84.78(15) . . . . ? C27 C22 C23 C24 -1.77(19) . . . . ? C16 C22 C23 C24 176.84(11) . . . . ? C22 C23 C24 F30 179.18(12) . . . . ? C22 C23 C24 C25 -0.3(2) . . . . ? F30 C24 C25 C26 -177.40(12) . . . . ? C23 C24 C25 C26 2.1(2) . . . . ? F30 C24 C25 C28 2.99(19) . . . . ? C23 C24 C25 C28 -177.50(12) . . . . ? C24 C25 C26 C27 -1.8(2) . . . . ? C28 C25 C26 C27 177.80(12) . . . . ? C25 C26 C27 C22 -0.3(2) . . . . ? C23 C22 C27 C26 2.1(2) . . . . ? C16 C22 C27 C26 -176.53(12) . . . . ? C24 C25 C28 N29 21(3) . . . . ? C26 C25 C28 N29 -159(3) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.199 _refine_diff_density_min -0.180 _refine_diff_density_rms 0.045 data_olsen17 _database_code_depnum_ccdc_archive 'CCDC 231345' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C8 H3 F2 N O' _chemical_formula_sum 'C8 H3 F2 N O' _chemical_formula_weight 167.11 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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 3.7369(2) _cell_length_b 6.2036(3) _cell_length_c 28.8526(18) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 668.87(6) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 801 _cell_measurement_theta_min 3.36 _cell_measurement_theta_max 27.45 _exptl_crystal_description 'Cut fragment' _exptl_crystal_colour colorless _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.660 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 336 _exptl_absorpt_coefficient_mu 0.149 _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 100(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Kappa CCD' _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_reflns_number 1401 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0469 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -36 _diffrn_reflns_limit_l_max 37 _diffrn_reflns_theta_min 3.36 _diffrn_reflns_theta_max 27.45 _reflns_number_total 1401 _reflns_number_gt 1267 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Kappa CCD' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'Denzo + Scalepak (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR92 (Altomare et Al., 1994)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP (Johnson,1976)' _computing_publication_material SHELXL97 _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^)+(0.0000P)^2^+0.2701P] 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 'H-atoms riding' _refine_ls_extinction_method SHELXL97 _refine_ls_extinction_coef 0.027(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.4(9) _refine_ls_number_reflns 1401 _refine_ls_number_parameters 113 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0405 _refine_ls_R_factor_gt 0.0327 _refine_ls_wR_factor_ref 0.0722 _refine_ls_wR_factor_gt 0.0677 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.052 _refine_ls_shift/su_max 0.002 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.3865(5) 0.0398(3) 0.59038(6) 0.0167(4) Uani 1 d . . . C2 C 0.2206(5) 0.2374(3) 0.58281(6) 0.0178(4) Uani 1 d . . . C3 C 0.1425(5) 0.3839(3) 0.61705(6) 0.0175(4) Uani 1 d . . . H3A H 0.0332 0.5183 0.6101 0.028(6) Uiso 1 calc R . . C4 C 0.2302(5) 0.3275(3) 0.66238(6) 0.0172(4) Uani 1 d . . . C5 C 0.3914(5) 0.1297(3) 0.67290(6) 0.0178(4) Uani 1 d . . . H5A H 0.4459 0.0909 0.7040 0.016(5) Uiso 1 calc R . . C6 C 0.4678(5) -0.0061(3) 0.63662(6) 0.0169(4) Uani 1 d . . . C7 C 0.4703(5) -0.1061(3) 0.55084(6) 0.0193(4) Uani 1 d . . . H7A H 0.3589 -0.0781 0.5219 0.027(5) Uiso 1 calc R . . O8 O 0.6723(4) -0.2586(2) 0.55350(4) 0.0268(3) Uani 1 d . . . C9 C 0.1519(5) 0.4766(3) 0.69961(6) 0.0193(4) Uani 1 d . . . N10 N 0.0928(5) 0.5968(2) 0.72867(5) 0.0260(4) Uani 1 d . . . F11 F 0.6281(3) -0.19524(15) 0.64655(3) 0.0228(3) Uani 1 d . . . F12 F 0.1293(3) 0.28762(17) 0.53878(3) 0.0258(3) Uani 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 0.0137(9) 0.0161(8) 0.0205(8) -0.0008(6) 0.0006(8) -0.0023(8) C2 0.0154(9) 0.0229(9) 0.0150(7) 0.0034(7) -0.0004(7) -0.0022(8) C3 0.0148(9) 0.0167(8) 0.0209(8) 0.0003(7) -0.0008(8) 0.0001(8) C4 0.0153(9) 0.0183(9) 0.0180(8) -0.0010(7) 0.0023(7) -0.0023(7) C5 0.0177(9) 0.0191(8) 0.0166(8) 0.0008(7) -0.0002(8) -0.0014(8) C6 0.0145(9) 0.0135(8) 0.0225(9) 0.0021(7) 0.0002(7) -0.0010(7) C7 0.0200(10) 0.0200(9) 0.0180(9) 0.0004(7) 0.0016(7) -0.0027(8) O8 0.0311(8) 0.0245(7) 0.0249(6) -0.0024(6) 0.0012(6) 0.0075(7) C9 0.0195(10) 0.0194(9) 0.0190(8) 0.0019(7) 0.0001(8) 0.0000(8) N10 0.0306(10) 0.0252(8) 0.0221(7) -0.0022(7) 0.0004(8) 0.0027(8) F11 0.0285(6) 0.0180(5) 0.0218(5) 0.0020(4) 0.0008(5) 0.0063(5) F12 0.0333(6) 0.0290(6) 0.0152(5) 0.0006(4) -0.0040(5) 0.0080(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 C2 1.391(2) . ? C1 C6 1.398(2) . ? C1 C7 1.489(2) . ? C2 F12 1.3518(18) . ? C2 C3 1.374(2) . ? C3 C4 1.393(2) . ? C4 C5 1.401(2) . ? C4 C9 1.447(2) . ? C5 C6 1.374(2) . ? C6 F11 1.3480(18) . ? C7 O8 1.213(2) . ? C9 N10 1.144(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C6 115.23(15) . . ? C2 C1 C7 120.60(15) . . ? C6 C1 C7 124.16(16) . . ? F12 C2 C3 118.02(16) . . ? F12 C2 C1 117.59(15) . . ? C3 C2 C1 124.39(15) . . ? C2 C3 C4 117.34(16) . . ? C3 C4 C5 121.65(16) . . ? C3 C4 C9 119.26(16) . . ? C5 C4 C9 119.09(15) . . ? C6 C5 C4 117.50(15) . . ? F11 C6 C5 117.66(16) . . ? F11 C6 C1 118.47(15) . . ? C5 C6 C1 123.87(16) . . ? O8 C7 C1 123.81(16) . . ? N10 C9 C4 178.9(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 C6 C1 C2 F12 -178.63(15) . . . . ? C7 C1 C2 F12 2.1(2) . . . . ? C6 C1 C2 C3 1.1(3) . . . . ? C7 C1 C2 C3 -178.18(17) . . . . ? F12 C2 C3 C4 178.45(16) . . . . ? C1 C2 C3 C4 -1.3(3) . . . . ? C2 C3 C4 C5 0.0(3) . . . . ? C2 C3 C4 C9 -179.81(17) . . . . ? C3 C4 C5 C6 1.4(3) . . . . ? C9 C4 C5 C6 -178.83(17) . . . . ? C4 C5 C6 F11 179.00(14) . . . . ? C4 C5 C6 C1 -1.6(3) . . . . ? C2 C1 C6 F11 179.82(14) . . . . ? C7 C1 C6 F11 -0.9(3) . . . . ? C2 C1 C6 C5 0.4(3) . . . . ? C7 C1 C6 C5 179.66(18) . . . . ? C2 C1 C7 O8 165.23(17) . . . . ? C6 C1 C7 O8 -14.0(3) . . . . ? C3 C4 C9 N10 -54(12) . . . . ? C5 C4 C9 N10 126(12) . . . . ? _diffrn_measured_fraction_theta_max 0.951 _diffrn_reflns_theta_full 27.45 _diffrn_measured_fraction_theta_full 0.951 _refine_diff_density_max 0.194 _refine_diff_density_min -0.197 _refine_diff_density_rms 0.042 data_olsen18 _database_code_depnum_ccdc_archive 'CCDC 231346' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C23 H19 CL F3 N3 O2 , H2O' _chemical_formula_sum 'C23 H21 Cl F3 N3 O3' _chemical_formula_weight 479.88 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.6360(6) _cell_length_b 6.9444(4) _cell_length_c 26.6949(16) _cell_angle_alpha 90.00 _cell_angle_beta 98.983(2) _cell_angle_gamma 90.00 _cell_volume 2130.63(17) _cell_formula_units_Z 4 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 2468 _cell_measurement_theta_min 3.03 _cell_measurement_theta_max 24.11 _exptl_crystal_description 'Cut fragment' _exptl_crystal_colour colorless _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.496 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 992 _exptl_absorpt_coefficient_mu 0.238 _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 223(2) _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Kappa CCD' _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_reflns_number 4227 _diffrn_reflns_av_R_equivalents 0.0326 _diffrn_reflns_av_sigmaI/netI 0.0496 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 3.03 _diffrn_reflns_theta_max 24.11 _reflns_number_total 2757 _reflns_number_gt 2354 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Kappa CCD' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'Denzo + Scalepak (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR92 (Altomare et Al., 1994)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP (Johnson,1976)' _computing_publication_material SHELXL97 _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^)+(0.0615P)^2^+4.5457P] 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 'H-atoms riding' _refine_ls_extinction_method SHELXL97 _refine_ls_extinction_coef 0.036(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2757 _refine_ls_number_parameters 321 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0782 _refine_ls_R_factor_gt 0.0664 _refine_ls_wR_factor_ref 0.1709 _refine_ls_wR_factor_gt 0.1639 _refine_ls_goodness_of_fit_ref 1.169 _refine_ls_restrained_S_all 1.169 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.9819(4) 0.2674(6) 0.28458(15) 0.0318(11) Uani 1 d . . . N2 N 0.8686(3) 0.2036(5) 0.28007(12) 0.0300(9) Uani 1 d . . . C3 C 0.8505(4) 0.0854(6) 0.32011(15) 0.0302(11) Uani 1 d . . . C4 C 0.9603(4) 0.0828(6) 0.35838(15) 0.0278(10) Uani 1 d . . . H4A H 0.9852 -0.0520 0.3656 0.039(13) Uiso 1 calc R . . C5 C 1.0512(4) 0.1878(6) 0.33272(15) 0.0293(11) Uani 1 d . . . H5A H 1.1086 0.0934 0.3239 0.041(13) Uiso 1 calc R . . O6 O 1.0190(3) 0.3692(5) 0.25355(12) 0.0479(10) Uani 1 d . . . O7 O 0.7607(3) 0.0024(5) 0.32277(11) 0.0400(9) Uani 1 d . . . C8 C 0.7893(4) 0.2097(7) 0.23193(15) 0.0360(12) Uani 1 d . . . H8A H 0.7472 0.0872 0.2278 0.024(11) Uiso 1 calc R . . H8B H 0.8362 0.2186 0.2045 0.050(14) Uiso 1 calc R . . C9 C 0.7011(4) 0.3708(7) 0.22510(15) 0.0328(11) Uani 1 d . . . C10 C 0.7200(5) 0.5488(7) 0.24797(16) 0.0348(12) Uani 1 d . . . H10A H 0.7882 0.5702 0.2712 0.050(15) Uiso 1 calc R . . C11 C 0.6401(5) 0.6961(7) 0.23711(18) 0.0417(13) Uani 1 d . . . H11A H 0.6516 0.8153 0.2538 0.046(14) Uiso 1 calc R . . C12 C 0.5437(4) 0.6645(7) 0.20149(18) 0.0400(13) Uani 1 d . . . C13 C 0.5214(5) 0.4903(8) 0.17815(19) 0.0466(14) Uani 1 d . . . H13A H 0.4538 0.4712 0.1543 0.056(17) Uiso 1 calc R . . C14 C 0.6003(5) 0.3433(7) 0.19042(18) 0.0423(13) Uani 1 d . . . H14A H 0.5856 0.2221 0.1750 0.035(12) Uiso 1 calc R . . F15 F 0.4685(3) 0.8132(5) 0.18883(12) 0.0609(9) Uani 1 d . . . C16 C 0.9528(4) 0.1892(6) 0.40880(15) 0.0279(11) Uani 1 d . . . H16A H 0.9583 0.0913 0.4360 0.025(11) Uiso 1 calc R . . N17 N 1.0608(3) 0.3120(5) 0.41855(12) 0.0260(9) Uani 1 d . . . C18 C 1.1559(4) 0.2283(7) 0.45732(16) 0.0333(11) Uani 1 d . . . H18A H 1.1576 0.0876 0.4549 0.062(17) Uiso 1 calc R . . H18B H 1.1455 0.2649 0.4918 0.038(12) Uiso 1 calc R . . C19 C 1.2653(4) 0.3160(8) 0.44336(17) 0.0395(12) Uani 1 d . . . H19A H 1.3341 0.2409 0.4575 0.035(13) Uiso 1 calc R . . H19B H 1.2754 0.4490 0.4555 0.054(15) Uiso 1 calc R . . C20 C 1.2446(4) 0.3082(8) 0.38530(16) 0.0374(12) Uani 1 d . . . H20A H 1.2881 0.4103 0.3712 0.052(15) Uiso 1 calc R . . H20B H 1.2688 0.1834 0.3733 0.071(19) Uiso 1 calc R . . C21 C 1.1139(4) 0.3371(6) 0.36974(15) 0.0288(11) Uani 1 d . . . H21A H 1.0981 0.4685 0.3560 0.039(13) Uiso 1 calc R . . C22 C 0.8422(4) 0.3057(6) 0.41012(14) 0.0280(11) Uani 1 d . . . C23 C 0.8201(4) 0.4843(6) 0.38854(14) 0.0283(11) Uani 1 d . . . C24 C 0.7257(4) 0.5984(7) 0.39424(15) 0.0356(12) Uani 1 d . . . H24A H 0.7160 0.7216 0.3796 0.035(12) Uiso 1 calc R . . C25 C 0.6456(4) 0.5235(7) 0.42248(16) 0.0372(12) Uani 1 d . . . C26 C 0.6596(4) 0.3344(7) 0.44230(17) 0.0384(12) Uani 1 d . . . H26A H 0.6036 0.2800 0.4599 0.10(2) Uiso 1 calc R . . C27 C 0.7561(4) 0.2331(6) 0.43536(16) 0.0330(11) Uani 1 d . . . C28 C 0.5470(5) 0.6359(8) 0.43185(18) 0.0442(13) Uani 1 d . . . N29 N 0.4707(5) 0.7243(8) 0.44028(18) 0.0617(14) Uani 1 d . . . F30 F 0.8971(2) 0.5561(3) 0.35978(9) 0.0342(7) Uani 1 d . . . F31 F 0.7668(2) 0.0526(4) 0.45337(10) 0.0431(8) Uani 1 d . . . Cl32 Cl 1.04694(11) 0.71811(16) 0.45995(4) 0.0383(4) Uani 1 d . . . H32 H 1.052 0.435 0.4299 0.032 Uiso 1 calc R . . O33 O 1.2192(4) 0.8107(6) 0.38756(14) 0.0634(11) Uani 1 d . . . H331 H 1.1668 0.7846 0.4122 0.088 Uiso 1 calc R . . H332 H 1.3286 0.8232 0.4048 0.250 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 C1 0.042(3) 0.029(3) 0.025(2) -0.0021(18) 0.006(2) -0.002(2) N2 0.037(3) 0.030(2) 0.0231(17) -0.0005(15) 0.0020(16) -0.0010(17) C3 0.038(3) 0.024(2) 0.029(2) -0.0079(17) 0.005(2) -0.001(2) C4 0.032(3) 0.025(2) 0.026(2) 0.0024(17) 0.0036(19) 0.0009(19) C5 0.037(3) 0.024(2) 0.028(2) -0.0004(17) 0.0076(19) -0.003(2) O6 0.059(3) 0.049(2) 0.0357(17) 0.0119(15) 0.0056(16) -0.0127(18) O7 0.041(2) 0.039(2) 0.0385(17) -0.0045(14) 0.0030(15) -0.0129(17) C8 0.048(4) 0.033(3) 0.025(2) -0.0033(18) -0.001(2) -0.001(2) C9 0.036(3) 0.036(3) 0.027(2) 0.0023(19) 0.006(2) -0.002(2) C10 0.037(3) 0.037(3) 0.030(2) 0.0005(19) 0.004(2) -0.006(2) C11 0.055(4) 0.031(3) 0.040(3) -0.004(2) 0.010(3) -0.001(2) C12 0.032(3) 0.047(3) 0.041(3) 0.004(2) 0.008(2) 0.008(2) C13 0.034(4) 0.058(4) 0.045(3) -0.003(2) -0.003(3) 0.008(3) C14 0.043(4) 0.043(3) 0.040(3) -0.013(2) 0.001(2) 0.001(2) F15 0.060(2) 0.059(2) 0.0625(19) 0.0038(16) 0.0046(16) 0.0256(17) C16 0.034(3) 0.026(2) 0.025(2) 0.0028(17) 0.0053(19) -0.004(2) N17 0.034(3) 0.019(2) 0.0256(17) -0.0017(14) 0.0052(16) 0.0000(16) C18 0.039(3) 0.031(3) 0.029(2) 0.0009(18) 0.003(2) 0.004(2) C19 0.031(3) 0.043(3) 0.042(3) -0.004(2) 0.002(2) 0.001(2) C20 0.030(4) 0.046(3) 0.035(2) -0.004(2) 0.004(2) -0.006(2) C21 0.033(3) 0.026(2) 0.028(2) 0.0022(17) 0.006(2) -0.0006(19) C22 0.035(3) 0.027(2) 0.0223(19) 0.0000(17) 0.0042(19) -0.001(2) C23 0.033(3) 0.031(3) 0.022(2) -0.0007(17) 0.0064(19) -0.004(2) C24 0.042(4) 0.036(3) 0.028(2) 0.0003(19) 0.004(2) 0.002(2) C25 0.033(3) 0.049(3) 0.029(2) -0.002(2) 0.004(2) 0.005(2) C26 0.034(3) 0.048(3) 0.033(2) 0.005(2) 0.007(2) -0.002(2) C27 0.039(3) 0.031(3) 0.028(2) 0.0016(18) 0.004(2) -0.002(2) C28 0.036(4) 0.054(3) 0.042(3) 0.007(2) 0.005(2) 0.012(3) N29 0.049(4) 0.077(4) 0.062(3) 0.009(3) 0.015(3) 0.017(3) F30 0.0385(18) 0.0320(15) 0.0334(13) 0.0073(10) 0.0098(12) 0.0013(11) F31 0.049(2) 0.0350(16) 0.0464(15) 0.0105(12) 0.0125(13) -0.0030(13) Cl32 0.0531(9) 0.0267(6) 0.0359(6) -0.0039(4) 0.0098(5) -0.0009(5) O33 0.076(3) 0.061(3) 0.058(2) 0.0041(19) 0.026(2) -0.002(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 C1 O6 1.218(5) . ? C1 N2 1.378(6) . ? C1 C5 1.511(6) . ? N2 C3 1.390(6) . ? N2 C8 1.461(5) . ? C3 O7 1.205(5) . ? C3 C4 1.506(7) . ? C4 C5 1.531(6) . ? C4 C16 1.550(6) . ? C5 C21 1.536(6) . ? C8 C9 1.510(7) . ? C9 C10 1.381(6) . ? C9 C14 1.390(7) . ? C10 C11 1.382(7) . ? C11 C12 1.370(7) . ? C12 F15 1.362(6) . ? C12 C13 1.367(8) . ? C13 C14 1.378(7) . ? C16 N17 1.507(6) . ? C16 C22 1.526(6) . ? N17 C18 1.508(6) . ? N17 C21 1.537(5) . ? C18 C19 1.510(7) . ? C19 C20 1.532(6) . ? C20 C21 1.525(7) . ? C22 C23 1.375(6) . ? C22 C27 1.387(6) . ? C23 F30 1.362(5) . ? C23 C24 1.382(6) . ? C24 C25 1.388(7) . ? C25 C26 1.415(7) . ? C25 C28 1.442(7) . ? C26 C27 1.362(7) . ? C27 F31 1.341(5) . ? C28 N29 1.130(6) . ? 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 O6 C1 N2 124.3(4) . . ? O6 C1 C5 126.3(5) . . ? N2 C1 C5 109.4(4) . . ? C1 N2 C3 112.4(4) . . ? C1 N2 C8 122.1(3) . . ? C3 N2 C8 122.9(4) . . ? O7 C3 N2 124.4(4) . . ? O7 C3 C4 127.3(4) . . ? N2 C3 C4 108.3(4) . . ? C3 C4 C5 105.2(3) . . ? C3 C4 C16 115.3(4) . . ? C5 C4 C16 107.3(3) . . ? C1 C5 C4 103.9(4) . . ? C1 C5 C21 115.9(4) . . ? C4 C5 C21 109.0(3) . . ? N2 C8 C9 116.9(4) . . ? C10 C9 C14 118.5(4) . . ? C10 C9 C8 123.4(4) . . ? C14 C9 C8 117.8(4) . . ? C11 C10 C9 120.9(5) . . ? C12 C11 C10 118.6(5) . . ? F15 C12 C13 119.3(5) . . ? F15 C12 C11 118.4(5) . . ? C13 C12 C11 122.3(5) . . ? C12 C13 C14 118.4(5) . . ? C13 C14 C9 121.2(5) . . ? N17 C16 C22 112.3(3) . . ? N17 C16 C4 105.2(3) . . ? C22 C16 C4 115.8(3) . . ? C18 N17 C16 113.8(3) . . ? C18 N17 C21 106.0(3) . . ? C16 N17 C21 110.6(3) . . ? N17 C18 C19 103.4(3) . . ? C18 C19 C20 103.3(4) . . ? C21 C20 C19 105.3(4) . . ? C20 C21 C5 116.1(4) . . ? C20 C21 N17 105.7(3) . . ? C5 C21 N17 104.8(3) . . ? C23 C22 C27 115.4(4) . . ? C23 C22 C16 124.9(4) . . ? C27 C22 C16 119.6(4) . . ? F30 C23 C22 118.0(4) . . ? F30 C23 C24 117.2(4) . . ? C22 C23 C24 124.8(4) . . ? C23 C24 C25 117.2(4) . . ? C24 C25 C26 120.2(4) . . ? C24 C25 C28 120.7(5) . . ? C26 C25 C28 119.1(4) . . ? C27 C26 C25 118.5(4) . . ? F31 C27 C26 117.8(4) . . ? F31 C27 C22 118.7(4) . . ? C26 C27 C22 123.5(4) . . ? N29 C28 C25 178.5(6) . . ? 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 O6 C1 N2 C3 178.3(4) . . . . ? C5 C1 N2 C3 -0.4(5) . . . . ? O6 C1 N2 C8 16.3(7) . . . . ? C5 C1 N2 C8 -162.5(4) . . . . ? C1 N2 C3 O7 -174.9(4) . . . . ? C8 N2 C3 O7 -13.0(6) . . . . ? C1 N2 C3 C4 5.7(5) . . . . ? C8 N2 C3 C4 167.6(4) . . . . ? O7 C3 C4 C5 172.2(4) . . . . ? N2 C3 C4 C5 -8.5(4) . . . . ? O7 C3 C4 C16 -69.8(6) . . . . ? N2 C3 C4 C16 109.6(4) . . . . ? O6 C1 C5 C4 176.4(4) . . . . ? N2 C1 C5 C4 -4.9(4) . . . . ? O6 C1 C5 C21 56.9(6) . . . . ? N2 C1 C5 C21 -124.5(4) . . . . ? C3 C4 C5 C1 7.9(4) . . . . ? C16 C4 C5 C1 -115.4(4) . . . . ? C3 C4 C5 C21 132.0(4) . . . . ? C16 C4 C5 C21 8.7(5) . . . . ? C1 N2 C8 C9 -101.9(5) . . . . ? C3 N2 C8 C9 97.9(5) . . . . ? N2 C8 C9 C10 29.6(6) . . . . ? N2 C8 C9 C14 -156.3(4) . . . . ? C14 C9 C10 C11 0.7(7) . . . . ? C8 C9 C10 C11 174.7(4) . . . . ? C9 C10 C11 C12 -2.7(7) . . . . ? C10 C11 C12 F15 -176.4(4) . . . . ? C10 C11 C12 C13 3.1(7) . . . . ? F15 C12 C13 C14 178.1(4) . . . . ? C11 C12 C13 C14 -1.3(8) . . . . ? C12 C13 C14 C9 -0.9(8) . . . . ? C10 C9 C14 C13 1.1(7) . . . . ? C8 C9 C14 C13 -173.2(4) . . . . ? C3 C4 C16 N17 -133.0(4) . . . . ? C5 C4 C16 N17 -16.1(4) . . . . ? C3 C4 C16 C22 -8.4(5) . . . . ? C5 C4 C16 C22 108.5(4) . . . . ? C22 C16 N17 C18 132.0(3) . . . . ? C4 C16 N17 C18 -101.3(4) . . . . ? C22 C16 N17 C21 -108.7(4) . . . . ? C4 C16 N17 C21 18.0(4) . . . . ? C16 N17 C18 C19 154.7(3) . . . . ? C21 N17 C18 C19 32.8(4) . . . . ? N17 C18 C19 C20 -40.8(4) . . . . ? C18 C19 C20 C21 33.4(5) . . . . ? C19 C20 C21 C5 -128.8(4) . . . . ? C19 C20 C21 N17 -13.2(5) . . . . ? C1 C5 C21 C20 -125.1(4) . . . . ? C4 C5 C21 C20 118.2(4) . . . . ? C1 C5 C21 N17 118.8(4) . . . . ? C4 C5 C21 N17 2.1(5) . . . . ? C18 N17 C21 C20 -12.0(4) . . . . ? C16 N17 C21 C20 -135.8(4) . . . . ? C18 N17 C21 C5 111.1(4) . . . . ? C16 N17 C21 C5 -12.7(4) . . . . ? N17 C16 C22 C23 42.6(5) . . . . ? C4 C16 C22 C23 -78.3(5) . . . . ? N17 C16 C22 C27 -136.2(4) . . . . ? C4 C16 C22 C27 103.0(4) . . . . ? C27 C22 C23 F30 -174.8(4) . . . . ? C16 C22 C23 F30 6.5(6) . . . . ? C27 C22 C23 C24 5.9(6) . . . . ? C16 C22 C23 C24 -172.9(4) . . . . ? F30 C23 C24 C25 178.4(4) . . . . ? C22 C23 C24 C25 -2.2(7) . . . . ? C23 C24 C25 C26 -2.7(6) . . . . ? C23 C24 C25 C28 177.7(4) . . . . ? C24 C25 C26 C27 3.5(7) . . . . ? C28 C25 C26 C27 -176.8(4) . . . . ? C25 C26 C27 F31 -178.5(4) . . . . ? C25 C26 C27 C22 0.5(7) . . . . ? C23 C22 C27 F31 174.1(4) . . . . ? C16 C22 C27 F31 -7.1(6) . . . . ? C23 C22 C27 C26 -4.9(6) . . . . ? C16 C22 C27 C26 173.9(4) . . . . ? C24 C25 C28 N29 -112(24) . . . . ? C26 C25 C28 N29 68(24) . . . . ? _diffrn_measured_fraction_theta_max 0.814 _diffrn_reflns_theta_full 24.11 _diffrn_measured_fraction_theta_full 0.814 _refine_diff_density_max 0.320 _refine_diff_density_min -0.267 _refine_diff_density_rms 0.060 data_olsen19 _database_code_depnum_ccdc_archive 'CCDC 231347' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C23 H18 F3 N3 O2' _chemical_formula_sum 'C23 H18 F3 N3 O2' _chemical_formula_weight 425.40 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/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 4.8890(7) _cell_length_b 20.180(2) _cell_length_c 19.844(2) _cell_angle_alpha 90.00 _cell_angle_beta 96.211(5) _cell_angle_gamma 90.00 _cell_volume 1946.3(4) _cell_formula_units_Z 4 _cell_measurement_temperature 243(2) _cell_measurement_reflns_used 2150 _cell_measurement_theta_min 3.20 _cell_measurement_theta_max 24.12 _exptl_crystal_description 'Cut fragment' _exptl_crystal_colour colorless _exptl_crystal_size_max 0.09 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.452 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 880 _exptl_absorpt_coefficient_mu 0.114 _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 243(2) _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Kappa CCD' _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_reflns_number 3963 _diffrn_reflns_av_R_equivalents 0.0658 _diffrn_reflns_av_sigmaI/netI 0.0732 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 3.20 _diffrn_reflns_theta_max 24.12 _reflns_number_total 2712 _reflns_number_gt 2225 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Kappa CCD' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'Denzo + Scalepak (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR92 (Altomare et Al., 1994)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP (Johnson,1976)' _computing_publication_material SHELXL97 _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^)+(0.0985P)^2^+11.3641P] 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 'H-atoms riding' _refine_ls_extinction_method SHELXL97 _refine_ls_extinction_coef 0.007(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2712 _refine_ls_number_parameters 299 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1434 _refine_ls_R_factor_gt 0.1252 _refine_ls_wR_factor_ref 0.3317 _refine_ls_wR_factor_gt 0.3214 _refine_ls_goodness_of_fit_ref 1.161 _refine_ls_restrained_S_all 1.161 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.0581(18) 0.4377(4) 0.7306(4) 0.049(2) Uani 1 d . . . N2 N -0.0061(14) 0.4637(3) 0.6664(3) 0.0451(17) Uani 1 d . . . C3 C -0.1977(16) 0.5159(4) 0.6653(4) 0.0444(19) Uani 1 d . . . C4 C -0.2622(16) 0.5278(3) 0.7372(4) 0.0395(18) Uani 1 d . . . H4A H -0.4625 0.5237 0.7398 0.036(19) Uiso 1 calc R . . C5 C -0.1071(16) 0.4728(4) 0.7793(4) 0.0426(18) Uani 1 d . . . H5A H -0.2375 0.4420 0.7979 0.12(5) Uiso 1 calc R . . O6 O 0.2239(14) 0.3929(3) 0.7426(3) 0.0622(18) Uani 1 d . . . O7 O -0.2924(13) 0.5428(3) 0.6143(3) 0.0562(16) Uani 1 d . . . C8 C 0.1029(19) 0.4389(4) 0.6052(5) 0.054(2) Uani 1 d . . . H8A H 0.2897 0.4219 0.6169 0.06(3) Uiso 1 calc R . . H8B H 0.1120 0.4753 0.5728 0.06(2) Uiso 1 calc R . . C9 C -0.0796(17) 0.3842(4) 0.5730(4) 0.0459(19) Uani 1 d . . . C10 C -0.2914(19) 0.3974(4) 0.5223(4) 0.052(2) Uani 1 d . . . H10A H -0.3186 0.4411 0.5065 0.030(18) Uiso 1 calc R . . C11 C -0.463(2) 0.3476(4) 0.4945(5) 0.057(2) Uani 1 d . . . H11A H -0.6062 0.3569 0.4602 0.09(4) Uiso 1 calc R . . C12 C -0.419(2) 0.2848(4) 0.5185(4) 0.057(2) Uani 1 d . . . C13 C -0.211(2) 0.2694(4) 0.5672(5) 0.063(3) Uani 1 d . . . H13A H -0.1807 0.2254 0.5817 0.05(2) Uiso 1 calc R . . C14 C -0.046(2) 0.3196(4) 0.5944(5) 0.057(2) Uani 1 d . . . H14A H 0.0952 0.3096 0.6289 0.09(4) Uiso 1 calc R . . F15 F -0.5862(15) 0.2359(3) 0.4912(3) 0.087(2) Uani 1 d . . . C16 C -0.1523(16) 0.5931(3) 0.7723(4) 0.0397(18) Uani 1 d . . . H16A H -0.2779 0.6050 0.8063 0.06(3) Uiso 1 calc R . . N17 N 0.1158(14) 0.5744(3) 0.8096(3) 0.0429(16) Uani 1 d . . . C18 C 0.1831(19) 0.6165(4) 0.8708(4) 0.046(2) Uani 1 d . . . H18A H 0.1152 0.6618 0.8621 0.06(2) Uiso 1 calc R . . H18B H 0.3828 0.6184 0.8828 0.08(3) Uiso 1 calc R . . C19 C 0.042(3) 0.5851(5) 0.9293(5) 0.067(3) Uani 1 d . . . H19A H 0.1721 0.5816 0.9704 0.16(7) Uiso 1 calc R . . H19B H -0.1156 0.6117 0.9394 0.4(2) Uiso 1 calc R . . C20 C -0.052(2) 0.5157(4) 0.9037(4) 0.055(2) Uani 1 d . . . H20A H -0.2527 0.5132 0.8962 0.15(6) Uiso 1 calc R . . H20B H 0.0157 0.4815 0.9364 0.08(3) Uiso 1 calc R . . C21 C 0.0756(17) 0.5070(3) 0.8364(4) 0.0442(19) Uani 1 d . . . H21A H 0.2546 0.4838 0.8446 0.05(2) Uiso 1 calc R . . C22 C -0.1235(15) 0.6536(3) 0.7284(4) 0.0374(17) Uani 1 d . . . C23 C 0.0610(16) 0.6591(3) 0.6805(4) 0.0416(18) Uani 1 d . . . C24 C 0.0954(17) 0.7157(4) 0.6425(4) 0.047(2) Uani 1 d . . . H24A H 0.2229 0.7168 0.6102 0.10(4) Uiso 1 calc R . . C25 C -0.0663(17) 0.7709(4) 0.6538(4) 0.0446(19) Uani 1 d . . . C26 C -0.2520(19) 0.7689(4) 0.7008(4) 0.051(2) Uani 1 d . . . H26A H -0.3587 0.8063 0.7088 0.04(2) Uiso 1 calc R . . C27 C -0.2781(15) 0.7112(4) 0.7359(4) 0.0409(18) Uani 1 d . . . C28 C -0.023(2) 0.8304(4) 0.6159(5) 0.057(2) Uani 1 d . . . N29 N 0.015(2) 0.8776(4) 0.5848(5) 0.075(3) Uani 1 d . . . F30 F 0.2209(10) 0.6067(2) 0.6699(2) 0.0552(14) Uani 1 d . . . F31 F -0.4630(10) 0.7099(2) 0.7821(2) 0.0549(13) Uani 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 0.045(5) 0.038(4) 0.062(5) -0.002(4) -0.001(4) -0.003(4) N2 0.054(4) 0.035(3) 0.047(4) 0.001(3) 0.005(3) -0.001(3) C3 0.039(4) 0.038(4) 0.055(5) 0.000(4) 0.000(4) -0.010(3) C4 0.036(4) 0.029(4) 0.054(5) 0.000(3) 0.005(3) -0.005(3) C5 0.042(5) 0.034(4) 0.051(5) 0.000(3) 0.002(3) 0.005(3) O6 0.067(4) 0.048(3) 0.067(4) -0.004(3) -0.007(3) 0.023(3) O7 0.065(4) 0.049(3) 0.053(3) 0.006(3) -0.004(3) 0.010(3) C8 0.051(6) 0.049(5) 0.065(5) -0.007(4) 0.017(4) -0.009(4) C9 0.049(5) 0.045(4) 0.045(4) -0.005(3) 0.010(4) 0.000(4) C10 0.061(6) 0.051(5) 0.044(5) -0.001(4) 0.005(4) 0.006(4) C11 0.062(6) 0.058(5) 0.051(5) -0.004(4) 0.002(4) 0.014(4) C12 0.068(6) 0.055(5) 0.047(5) 0.002(4) -0.002(4) -0.016(4) C13 0.086(7) 0.039(4) 0.060(6) 0.007(4) -0.007(5) -0.009(4) C14 0.065(6) 0.044(5) 0.059(5) -0.001(4) -0.005(5) 0.000(4) F15 0.109(5) 0.064(3) 0.080(4) -0.010(3) -0.026(4) -0.015(3) C16 0.044(5) 0.033(4) 0.044(4) -0.003(3) 0.010(3) -0.003(3) N17 0.045(4) 0.042(3) 0.042(4) 0.000(3) 0.005(3) -0.005(3) C18 0.055(5) 0.037(4) 0.045(4) 0.003(3) 0.002(4) -0.002(4) C19 0.091(8) 0.063(6) 0.049(5) 0.001(4) 0.019(5) -0.021(5) C20 0.074(7) 0.043(4) 0.048(5) 0.003(4) 0.009(4) -0.005(4) C21 0.046(5) 0.030(4) 0.056(5) 0.007(3) 0.004(4) 0.001(3) C22 0.042(4) 0.032(4) 0.037(4) 0.003(3) 0.000(3) -0.006(3) C23 0.042(4) 0.032(4) 0.051(5) 0.005(3) 0.005(4) 0.005(3) C24 0.048(5) 0.048(5) 0.044(4) 0.006(3) 0.001(4) -0.005(4) C25 0.048(5) 0.035(4) 0.049(5) 0.003(3) -0.001(4) -0.003(3) C26 0.062(6) 0.031(4) 0.057(5) -0.005(3) -0.004(4) 0.004(4) C27 0.034(4) 0.036(4) 0.054(5) -0.004(3) 0.012(3) -0.002(3) C28 0.071(6) 0.035(4) 0.060(5) 0.004(4) -0.012(4) -0.014(4) N29 0.092(7) 0.051(5) 0.078(6) 0.011(4) -0.010(5) -0.020(4) F30 0.058(3) 0.046(3) 0.064(3) 0.009(2) 0.020(2) 0.014(2) F31 0.061(3) 0.043(2) 0.063(3) -0.002(2) 0.017(2) 0.005(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 C1 O6 1.221(10) . ? C1 N2 1.381(11) . ? C1 C5 1.504(12) . ? N2 C3 1.409(10) . ? N2 C8 1.465(11) . ? C3 O7 1.196(9) . ? C3 C4 1.513(11) . ? C4 C5 1.539(10) . ? C4 C16 1.558(10) . ? C5 C21 1.529(11) . ? C8 C9 1.517(11) . ? C9 C14 1.375(11) . ? C9 C10 1.390(12) . ? C10 C11 1.386(13) . ? C11 C12 1.363(13) . ? C12 F15 1.355(10) . ? C12 C13 1.363(13) . ? C13 C14 1.368(12) . ? C16 N17 1.483(10) . ? C16 C22 1.515(10) . ? N17 C21 1.482(9) . ? N17 C18 1.490(10) . ? C18 C19 1.547(12) . ? C19 C20 1.542(12) . ? C20 C21 1.542(12) . ? C22 C23 1.383(11) . ? C22 C27 1.404(10) . ? C23 F30 1.345(8) . ? C23 C24 1.389(11) . ? C24 C25 1.398(12) . ? C25 C26 1.371(13) . ? C25 C28 1.444(11) . ? C26 C27 1.369(11) . ? C27 F31 1.356(9) . ? C28 N29 1.162(11) . ? 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 O6 C1 N2 122.8(8) . . ? O6 C1 C5 127.9(8) . . ? N2 C1 C5 109.3(7) . . ? C1 N2 C3 112.5(7) . . ? C1 N2 C8 124.6(7) . . ? C3 N2 C8 122.9(7) . . ? O7 C3 N2 123.2(8) . . ? O7 C3 C4 128.6(8) . . ? N2 C3 C4 108.1(6) . . ? C3 C4 C5 104.9(6) . . ? C3 C4 C16 117.3(6) . . ? C5 C4 C16 104.0(6) . . ? C1 C5 C21 112.2(7) . . ? C1 C5 C4 105.0(6) . . ? C21 C5 C4 107.0(6) . . ? N2 C8 C9 110.3(7) . . ? C14 C9 C10 117.4(8) . . ? C14 C9 C8 121.0(8) . . ? C10 C9 C8 121.5(8) . . ? C11 C10 C9 121.4(8) . . ? C12 C11 C10 118.0(8) . . ? F15 C12 C11 118.2(8) . . ? F15 C12 C13 119.3(8) . . ? C11 C12 C13 122.5(8) . . ? C12 C13 C14 118.3(8) . . ? C13 C14 C9 122.3(8) . . ? N17 C16 C22 111.1(6) . . ? N17 C16 C4 104.6(6) . . ? C22 C16 C4 118.3(6) . . ? C21 N17 C16 105.6(6) . . ? C21 N17 C18 104.9(6) . . ? C16 N17 C18 111.6(6) . . ? N17 C18 C19 107.4(6) . . ? C20 C19 C18 105.5(7) . . ? C19 C20 C21 104.8(7) . . ? N17 C21 C5 103.7(6) . . ? N17 C21 C20 106.6(6) . . ? C5 C21 C20 115.8(7) . . ? C23 C22 C27 113.8(6) . . ? C23 C22 C16 124.6(7) . . ? C27 C22 C16 121.5(7) . . ? F30 C23 C22 118.5(6) . . ? F30 C23 C24 117.0(7) . . ? C22 C23 C24 124.5(7) . . ? C23 C24 C25 117.6(8) . . ? C26 C25 C24 120.9(7) . . ? C26 C25 C28 121.6(8) . . ? C24 C25 C28 117.5(8) . . ? C27 C26 C25 118.4(7) . . ? F31 C27 C26 117.7(7) . . ? F31 C27 C22 117.5(6) . . ? C26 C27 C22 124.8(8) . . ? N29 C28 C25 178.8(12) . . ? 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 O6 C1 N2 C3 -178.6(7) . . . . ? C5 C1 N2 C3 1.8(9) . . . . ? O6 C1 N2 C8 3.4(13) . . . . ? C5 C1 N2 C8 -176.2(7) . . . . ? C1 N2 C3 O7 -175.7(7) . . . . ? C8 N2 C3 O7 2.3(12) . . . . ? C1 N2 C3 C4 2.1(9) . . . . ? C8 N2 C3 C4 -179.9(7) . . . . ? O7 C3 C4 C5 172.8(8) . . . . ? N2 C3 C4 C5 -4.8(8) . . . . ? O7 C3 C4 C16 -72.5(11) . . . . ? N2 C3 C4 C16 109.9(7) . . . . ? O6 C1 C5 C21 59.9(11) . . . . ? N2 C1 C5 C21 -120.5(7) . . . . ? O6 C1 C5 C4 175.7(8) . . . . ? N2 C1 C5 C4 -4.7(8) . . . . ? C3 C4 C5 C1 5.7(8) . . . . ? C16 C4 C5 C1 -118.0(7) . . . . ? C3 C4 C5 C21 125.0(7) . . . . ? C16 C4 C5 C21 1.3(8) . . . . ? C1 N2 C8 C9 88.5(10) . . . . ? C3 N2 C8 C9 -89.3(9) . . . . ? N2 C8 C9 C14 -85.1(10) . . . . ? N2 C8 C9 C10 93.2(9) . . . . ? C14 C9 C10 C11 0.4(13) . . . . ? C8 C9 C10 C11 -177.9(8) . . . . ? C9 C10 C11 C12 0.1(14) . . . . ? C10 C11 C12 F15 -179.7(8) . . . . ? C10 C11 C12 C13 -1.4(15) . . . . ? F15 C12 C13 C14 -179.5(9) . . . . ? C11 C12 C13 C14 2.2(16) . . . . ? C12 C13 C14 C9 -1.7(16) . . . . ? C10 C9 C14 C13 0.5(14) . . . . ? C8 C9 C14 C13 178.8(9) . . . . ? C3 C4 C16 N17 -93.5(7) . . . . ? C5 C4 C16 N17 21.7(8) . . . . ? C3 C4 C16 C22 30.7(10) . . . . ? C5 C4 C16 C22 145.9(7) . . . . ? C22 C16 N17 C21 -166.4(6) . . . . ? C4 C16 N17 C21 -37.8(7) . . . . ? C22 C16 N17 C18 80.1(7) . . . . ? C4 C16 N17 C18 -151.3(6) . . . . ? C21 N17 C18 C19 -28.5(9) . . . . ? C16 N17 C18 C19 85.3(8) . . . . ? N17 C18 C19 C20 12.4(11) . . . . ? C18 C19 C20 C21 7.8(11) . . . . ? C16 N17 C21 C5 38.4(8) . . . . ? C18 N17 C21 C5 156.4(6) . . . . ? C16 N17 C21 C20 -84.3(7) . . . . ? C18 N17 C21 C20 33.7(8) . . . . ? C1 C5 C21 N17 90.7(7) . . . . ? C4 C5 C21 N17 -23.8(8) . . . . ? C1 C5 C21 C20 -152.8(7) . . . . ? C4 C5 C21 C20 92.6(8) . . . . ? C19 C20 C21 N17 -25.6(10) . . . . ? C19 C20 C21 C5 -140.5(8) . . . . ? N17 C16 C22 C23 54.3(9) . . . . ? C4 C16 C22 C23 -66.6(10) . . . . ? N17 C16 C22 C27 -122.4(7) . . . . ? C4 C16 C22 C27 116.7(8) . . . . ? C27 C22 C23 F30 179.4(6) . . . . ? C16 C22 C23 F30 2.5(11) . . . . ? C27 C22 C23 C24 -0.1(11) . . . . ? C16 C22 C23 C24 -177.0(7) . . . . ? F30 C23 C24 C25 -179.0(7) . . . . ? C22 C23 C24 C25 0.5(12) . . . . ? C23 C24 C25 C26 0.0(12) . . . . ? C23 C24 C25 C28 177.8(7) . . . . ? C24 C25 C26 C27 -0.9(12) . . . . ? C28 C25 C26 C27 -178.6(8) . . . . ? C25 C26 C27 F31 -179.8(7) . . . . ? C25 C26 C27 C22 1.4(12) . . . . ? C23 C22 C27 F31 -179.7(6) . . . . ? C16 C22 C27 F31 -2.6(11) . . . . ? C23 C22 C27 C26 -0.9(11) . . . . ? C16 C22 C27 C26 176.1(7) . . . . ? C26 C25 C28 N29 -175(100) . . . . ? C24 C25 C28 N29 7(52) . . . . ? _diffrn_measured_fraction_theta_max 0.871 _diffrn_reflns_theta_full 24.12 _diffrn_measured_fraction_theta_full 0.871 _refine_diff_density_max 0.351 _refine_diff_density_min -0.336 _refine_diff_density_rms 0.080