# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_name 'Sang-gi Lee' _publ_contact_author_email SANGGI@EWHA.AC.KR _publ_section_title ; An effective and general method for highly regioselective synthesis of 1-phenypyrazoles from beta-enaminoketoesters, tandem Blaise-acylation adducts ; loop_ _publ_author_name 'Sang-gi Lee' 'Sungho Ahn' 'Yu Sung Chun' 'Jongki Hong' 'Youngmee Kim' ; Young Ok Ko ; 'Cho-Long Park' 'Hyunik Shin' # Attachment 'x-ray_data.cif.cif' data_2a _database_code_depnum_ccdc_archive 'CCDC 708928' _audit_creation_method SHELXTL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H18 N2 O2' _chemical_formula_weight 306.35 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/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 8.2775(12) _cell_length_b 15.616(2) _cell_length_c 12.3892(18) _cell_angle_alpha 90.00 _cell_angle_beta 98.896(3) _cell_angle_gamma 90.00 _cell_volume 1582.2(4) _cell_formula_units_Z 4 _cell_measurement_temperature 170(2) _cell_measurement_reflns_used 840 _cell_measurement_theta_min 2.61 _cell_measurement_theta_max 19.67 _exptl_crystal_description block _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.13 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.286 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 648 _exptl_absorpt_coefficient_mu 0.084 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.992 _exptl_absorpt_correction_T_max 0.993 _exptl_absorpt_process_details '(SADABS; Bruker, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 170(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8739 _diffrn_reflns_av_R_equivalents 0.0571 _diffrn_reflns_av_sigmaI/netI 0.0714 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.11 _diffrn_reflns_theta_max 26.00 _reflns_number_total 3094 _reflns_number_gt 1862 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0444P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0065(10) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3094 _refine_ls_number_parameters 211 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0793 _refine_ls_R_factor_gt 0.0421 _refine_ls_wR_factor_ref 0.0943 _refine_ls_wR_factor_gt 0.0862 _refine_ls_goodness_of_fit_ref 0.885 _refine_ls_restrained_S_all 0.885 _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 0.7523(2) 0.90071(10) 0.98010(13) 0.0285(4) Uani 1 1 d . . . C2 C 0.7237(2) 0.97692(10) 1.03702(12) 0.0284(4) Uani 1 1 d . . . C3 C 0.7613(2) 1.04377(11) 0.97179(13) 0.0305(4) Uani 1 1 d . . . C4 C 0.7391(2) 0.80937(10) 1.00842(13) 0.0290(4) Uani 1 1 d . . . C5 C 0.6747(2) 0.75167(11) 0.92821(14) 0.0340(4) Uani 1 1 d . . . H5 H 0.6364 0.7717 0.8564 0.041 Uiso 1 1 calc R . . C6 C 0.6654(2) 0.66551(11) 0.95105(15) 0.0392(5) Uani 1 1 d . . . H6 H 0.6192 0.6268 0.8956 0.047 Uiso 1 1 calc R . . C7 C 0.7237(2) 0.63569(12) 1.05505(15) 0.0404(5) Uani 1 1 d . . . H7 H 0.7181 0.5764 1.0711 0.048 Uiso 1 1 calc R . . C8 C 0.7894(2) 0.69213(12) 1.13494(15) 0.0401(5) Uani 1 1 d . . . H8 H 0.8300 0.6716 1.2061 0.048 Uiso 1 1 calc R . . C9 C 0.7971(2) 0.77848(11) 1.11265(14) 0.0347(5) Uani 1 1 d . . . H9 H 0.8422 0.8170 1.1686 0.042 Uiso 1 1 calc R . . C10 C 0.6516(2) 0.98271(11) 1.13753(13) 0.0306(4) Uani 1 1 d . . . C11 C 0.5903(2) 1.07657(11) 1.27715(13) 0.0372(5) Uani 1 1 d . . . H11A H 0.6242 1.0300 1.3300 0.045 Uiso 1 1 calc R . . H11B H 0.4693 1.0777 1.2614 0.045 Uiso 1 1 calc R . . C12 C 0.6543(2) 1.16077(12) 1.32298(14) 0.0470(5) Uani 1 1 d . . . H12A H 0.7740 1.1588 1.3382 0.071 Uiso 1 1 calc R . . H12B H 0.6111 1.1724 1.3908 0.071 Uiso 1 1 calc R . . H12C H 0.6199 1.2063 1.2699 0.071 Uiso 1 1 calc R . . C13 C 0.7656(2) 1.13859(10) 0.98996(14) 0.0404(5) Uani 1 1 d . . . H13A H 0.8309 1.1656 0.9398 0.061 Uiso 1 1 calc R . . H13B H 0.8147 1.1508 1.0655 0.061 Uiso 1 1 calc R . . H13C H 0.6540 1.1614 0.9764 0.061 Uiso 1 1 calc R . . C14 C 0.8440(2) 1.04605(11) 0.78446(13) 0.0291(4) Uani 1 1 d . . . C15 C 0.7527(2) 1.11303(11) 0.73610(14) 0.0381(5) Uani 1 1 d . . . H15 H 0.6617 1.1337 0.7666 0.046 Uiso 1 1 calc R . . C16 C 0.7937(2) 1.15005(12) 0.64303(14) 0.0441(5) Uani 1 1 d . . . H16 H 0.7320 1.1971 0.6101 0.053 Uiso 1 1 calc R . . C17 C 0.9243(2) 1.11907(12) 0.59729(15) 0.0433(5) Uani 1 1 d . . . H17 H 0.9541 1.1456 0.5342 0.052 Uiso 1 1 calc R . . C18 C 1.0104(2) 1.04987(12) 0.64355(14) 0.0394(5) Uani 1 1 d . . . H18 H 1.0977 1.0272 0.6108 0.047 Uiso 1 1 calc R . . C19 C 0.9714(2) 1.01284(11) 0.73750(13) 0.0330(4) Uani 1 1 d . . . H19 H 1.0316 0.9650 0.7695 0.040 Uiso 1 1 calc R . . N1 N 0.80464(17) 1.00706(8) 0.88146(10) 0.0296(4) Uani 1 1 d . . . N2 N 0.80224(17) 0.91929(8) 0.88587(11) 0.0313(4) Uani 1 1 d . . . O1 O 0.59209(14) 0.92351(8) 1.18073(9) 0.0393(3) Uani 1 1 d . . . O2 O 0.65786(14) 1.06288(7) 1.17762(9) 0.0352(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 0.0289(10) 0.0354(10) 0.0202(9) 0.0025(8) 0.0007(8) -0.0009(8) C2 0.0313(10) 0.0311(10) 0.0231(9) 0.0015(8) 0.0050(8) -0.0009(8) C3 0.0320(11) 0.0339(10) 0.0254(10) -0.0016(8) 0.0036(8) 0.0005(8) C4 0.0318(10) 0.0314(10) 0.0254(10) 0.0003(8) 0.0093(8) 0.0029(8) C5 0.0388(12) 0.0342(11) 0.0287(10) 0.0015(8) 0.0040(9) 0.0026(9) C6 0.0389(12) 0.0341(11) 0.0455(12) -0.0046(9) 0.0093(10) 0.0011(9) C7 0.0440(13) 0.0324(11) 0.0490(13) 0.0056(10) 0.0202(10) 0.0047(9) C8 0.0500(13) 0.0394(12) 0.0333(11) 0.0103(9) 0.0139(9) 0.0107(10) C9 0.0424(12) 0.0350(11) 0.0273(10) 0.0012(8) 0.0075(9) 0.0021(9) C10 0.0315(11) 0.0329(11) 0.0273(10) 0.0016(8) 0.0040(8) 0.0013(8) C11 0.0407(11) 0.0469(12) 0.0262(10) -0.0007(9) 0.0124(9) 0.0043(9) C12 0.0554(14) 0.0527(13) 0.0343(11) -0.0100(10) 0.0111(10) -0.0052(10) C13 0.0547(13) 0.0321(11) 0.0367(11) -0.0013(9) 0.0139(10) -0.0031(9) C14 0.0346(10) 0.0309(10) 0.0222(9) 0.0001(8) 0.0053(8) -0.0055(8) C15 0.0408(12) 0.0401(11) 0.0357(11) 0.0075(9) 0.0134(9) 0.0030(9) C16 0.0466(13) 0.0475(13) 0.0398(12) 0.0152(10) 0.0115(10) 0.0037(10) C17 0.0429(13) 0.0549(13) 0.0336(11) 0.0108(10) 0.0110(10) -0.0047(10) C18 0.0394(12) 0.0481(12) 0.0325(11) 0.0009(9) 0.0113(9) -0.0006(10) C19 0.0323(11) 0.0362(10) 0.0299(10) -0.0001(8) 0.0036(8) -0.0012(8) N1 0.0375(9) 0.0281(8) 0.0243(8) 0.0022(6) 0.0081(7) -0.0018(7) N2 0.0400(9) 0.0264(8) 0.0271(8) 0.0013(6) 0.0043(7) -0.0001(7) O1 0.0441(8) 0.0396(8) 0.0367(7) 0.0017(6) 0.0136(6) -0.0047(6) O2 0.0450(8) 0.0359(7) 0.0271(7) -0.0018(6) 0.0133(6) 0.0012(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 1.329(2) . ? C1 C2 1.422(2) . ? C1 C4 1.477(2) . ? C2 C3 1.385(2) . ? C2 C10 1.464(2) . ? C3 N1 1.3544(19) . ? C3 C13 1.497(2) . ? C4 C5 1.386(2) . ? C4 C9 1.393(2) . ? C5 C6 1.379(2) . ? C5 H5 0.9500 . ? C6 C7 1.385(2) . ? C6 H6 0.9500 . ? C7 C8 1.373(2) . ? C7 H7 0.9500 . ? C8 C9 1.380(2) . ? C8 H8 0.9500 . ? C9 H9 0.9500 . ? C10 O1 1.2107(19) . ? C10 O2 1.3449(19) . ? C11 O2 1.4466(18) . ? C11 C12 1.496(2) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 C15 1.373(2) . ? C14 C19 1.382(2) . ? C14 N1 1.4292(19) . ? C15 C16 1.378(2) . ? C15 H15 0.9500 . ? C16 C17 1.383(2) . ? C16 H16 0.9500 . ? C17 C18 1.370(2) . ? C17 H17 0.9500 . ? C18 C19 1.382(2) . ? C18 H18 0.9500 . ? C19 H19 0.9500 . ? N1 N2 1.3719(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 N2 C1 C2 110.57(14) . . ? N2 C1 C4 117.64(14) . . ? C2 C1 C4 131.78(15) . . ? C3 C2 C1 105.77(14) . . ? C3 C2 C10 127.41(15) . . ? C1 C2 C10 126.49(15) . . ? N1 C3 C2 105.98(14) . . ? N1 C3 C13 122.66(14) . . ? C2 C3 C13 131.31(15) . . ? C5 C4 C9 118.63(16) . . ? C5 C4 C1 119.48(15) . . ? C9 C4 C1 121.82(15) . . ? C6 C5 C4 120.97(17) . . ? C6 C5 H5 119.5 . . ? C4 C5 H5 119.5 . . ? C5 C6 C7 119.77(18) . . ? C5 C6 H6 120.1 . . ? C7 C6 H6 120.1 . . ? C8 C7 C6 119.80(17) . . ? C8 C7 H7 120.1 . . ? C6 C7 H7 120.1 . . ? C7 C8 C9 120.56(17) . . ? C7 C8 H8 119.7 . . ? C9 C8 H8 119.7 . . ? C8 C9 C4 120.27(17) . . ? C8 C9 H9 119.9 . . ? C4 C9 H9 119.9 . . ? O1 C10 O2 122.85(15) . . ? O1 C10 C2 125.17(16) . . ? O2 C10 C2 111.98(14) . . ? O2 C11 C12 106.99(14) . . ? O2 C11 H11A 110.3 . . ? C12 C11 H11A 110.3 . . ? O2 C11 H11B 110.3 . . ? C12 C11 H11B 110.3 . . ? H11A C11 H11B 108.6 . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C3 C13 H13A 109.5 . . ? C3 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C3 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C15 C14 C19 120.46(15) . . ? C15 C14 N1 120.64(15) . . ? C19 C14 N1 118.84(15) . . ? C14 C15 C16 119.62(17) . . ? C14 C15 H15 120.2 . . ? C16 C15 H15 120.2 . . ? C15 C16 C17 120.35(18) . . ? C15 C16 H16 119.8 . . ? C17 C16 H16 119.8 . . ? C18 C17 C16 119.57(17) . . ? C18 C17 H17 120.2 . . ? C16 C17 H17 120.2 . . ? C17 C18 C19 120.52(17) . . ? C17 C18 H18 119.7 . . ? C19 C18 H18 119.7 . . ? C14 C19 C18 119.38(17) . . ? C14 C19 H19 120.3 . . ? C18 C19 H19 120.3 . . ? C3 N1 N2 112.50(13) . . ? C3 N1 C14 129.68(14) . . ? N2 N1 C14 117.76(13) . . ? C1 N2 N1 105.15(13) . . ? C10 O2 C11 117.05(13) . . ? 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 N2 C1 C2 C3 -0.68(19) . . . . ? C4 C1 C2 C3 178.08(17) . . . . ? N2 C1 C2 C10 173.09(15) . . . . ? C4 C1 C2 C10 -8.1(3) . . . . ? C1 C2 C3 N1 1.53(18) . . . . ? C10 C2 C3 N1 -172.17(16) . . . . ? C1 C2 C3 C13 -175.78(18) . . . . ? C10 C2 C3 C13 10.5(3) . . . . ? N2 C1 C4 C5 -41.4(2) . . . . ? C2 C1 C4 C5 139.95(19) . . . . ? N2 C1 C4 C9 135.40(17) . . . . ? C2 C1 C4 C9 -43.3(3) . . . . ? C9 C4 C5 C6 1.1(3) . . . . ? C1 C4 C5 C6 177.92(15) . . . . ? C4 C5 C6 C7 -1.1(3) . . . . ? C5 C6 C7 C8 0.4(3) . . . . ? C6 C7 C8 C9 0.4(3) . . . . ? C7 C8 C9 C4 -0.4(3) . . . . ? C5 C4 C9 C8 -0.3(3) . . . . ? C1 C4 C9 C8 -177.08(16) . . . . ? C3 C2 C10 O1 165.07(17) . . . . ? C1 C2 C10 O1 -7.4(3) . . . . ? C3 C2 C10 O2 -14.6(2) . . . . ? C1 C2 C10 O2 172.97(16) . . . . ? C19 C14 C15 C16 -3.3(3) . . . . ? N1 C14 C15 C16 179.52(15) . . . . ? C14 C15 C16 C17 1.2(3) . . . . ? C15 C16 C17 C18 1.6(3) . . . . ? C16 C17 C18 C19 -2.3(3) . . . . ? C15 C14 C19 C18 2.6(3) . . . . ? N1 C14 C19 C18 179.85(15) . . . . ? C17 C18 C19 C14 0.2(3) . . . . ? C2 C3 N1 N2 -1.92(19) . . . . ? C13 C3 N1 N2 175.67(15) . . . . ? C2 C3 N1 C14 175.19(15) . . . . ? C13 C3 N1 C14 -7.2(3) . . . . ? C15 C14 N1 C3 -42.8(3) . . . . ? C19 C14 N1 C3 139.93(18) . . . . ? C15 C14 N1 N2 134.19(17) . . . . ? C19 C14 N1 N2 -43.1(2) . . . . ? C2 C1 N2 N1 -0.44(18) . . . . ? C4 C1 N2 N1 -179.41(14) . . . . ? C3 N1 N2 C1 1.49(18) . . . . ? C14 N1 N2 C1 -176.00(14) . . . . ? O1 C10 O2 C11 0.4(2) . . . . ? C2 C10 O2 C11 -179.95(14) . . . . ? C12 C11 O2 C10 163.40(15) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.176 _refine_diff_density_min -0.157 _refine_diff_density_rms 0.038 data_2b _database_code_depnum_ccdc_archive 'CCDC 708929' _audit_creation_method SHELXTL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H18 N2 O2' _chemical_formula_weight 306.35 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 10.468(8) _cell_length_b 15.676(12) _cell_length_c 10.469(8) _cell_angle_alpha 90.00 _cell_angle_beta 103.79 _cell_angle_gamma 90.00 _cell_volume 1668(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 971 _cell_measurement_theta_min 2.39 _cell_measurement_theta_max 18.78 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.220 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 648 _exptl_absorpt_coefficient_mu 0.080 _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 293(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9153 _diffrn_reflns_av_R_equivalents 0.1063 _diffrn_reflns_av_sigmaI/netI 0.1807 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.39 _diffrn_reflns_theta_max 25.99 _reflns_number_total 3264 _reflns_number_gt 1837 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0670P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.017(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3264 _refine_ls_number_parameters 211 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1489 _refine_ls_R_factor_gt 0.0587 _refine_ls_wR_factor_ref 0.1464 _refine_ls_wR_factor_gt 0.1324 _refine_ls_goodness_of_fit_ref 0.881 _refine_ls_restrained_S_all 0.881 _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 0.6757(3) 0.10107(18) 0.1206(3) 0.0583(8) Uani 1 1 d . . . C2 C 0.7251(3) 0.03934(18) 0.2145(3) 0.0631(9) Uani 1 1 d . . . C3 C 0.6218(4) 0.01559(19) 0.2697(3) 0.0684(9) Uani 1 1 d . . . C4 C 0.7324(3) 0.14942(18) 0.0267(3) 0.0604(8) Uani 1 1 d . . . C5 C 0.8419(3) 0.2009(2) 0.0713(3) 0.0750(10) Uani 1 1 d . . . H5 H 0.8817 0.2046 0.1606 0.090 Uiso 1 1 calc R . . C6 C 0.8900(4) 0.2462(2) -0.0191(5) 0.0969(12) Uani 1 1 d . . . H6 H 0.9636 0.2806 0.0100 0.116 Uiso 1 1 calc R . . C7 C 0.8325(5) 0.2424(3) -0.1519(5) 0.1062(14) Uani 1 1 d . . . H7 H 0.8656 0.2751 -0.2108 0.127 Uiso 1 1 calc R . . C8 C 0.7265(5) 0.1903(3) -0.1968(4) 0.1077(14) Uani 1 1 d . . . H8 H 0.6887 0.1859 -0.2865 0.129 Uiso 1 1 calc R . . C9 C 0.6765(3) 0.1446(2) -0.1078(4) 0.0809(10) Uani 1 1 d . . . H9 H 0.6038 0.1096 -0.1380 0.097 Uiso 1 1 calc R . . C10 C 0.8534(4) -0.0007(2) 0.2506(4) 0.0792(11) Uani 1 1 d . . . C11 C 1.0605(4) -0.0110(3) 0.1932(4) 0.1286(16) Uani 1 1 d . . . H11A H 1.0689 -0.0611 0.2489 0.154 Uiso 1 1 calc R . . H11B H 1.0828 -0.0272 0.1118 0.154 Uiso 1 1 calc R . . C12 C 1.1481(4) 0.0522(3) 0.2564(5) 0.167(2) Uani 1 1 d . . . H12A H 1.1321 0.1042 0.2066 0.251 Uiso 1 1 calc R . . H12B H 1.2368 0.0338 0.2630 0.251 Uiso 1 1 calc R . . H12C H 1.1350 0.0619 0.3430 0.251 Uiso 1 1 calc R . . C13 C 0.6150(3) -0.0489(2) 0.3742(3) 0.1088(13) Uani 1 1 d . . . H13A H 0.5248 -0.0582 0.3761 0.163 Uiso 1 1 calc R . . H13B H 0.6629 -0.0281 0.4583 0.163 Uiso 1 1 calc R . . H13C H 0.6530 -0.1017 0.3550 0.163 Uiso 1 1 calc R . . C14 C 0.4529(3) 0.1709(2) 0.0575(3) 0.0582(8) Uani 1 1 d . . . C15 C 0.4835(3) 0.2568(2) 0.0513(3) 0.0703(9) Uani 1 1 d . . . H15 H 0.5678 0.2768 0.0884 0.084 Uiso 1 1 calc R . . C16 C 0.3850(3) 0.3115(2) -0.0117(3) 0.0774(10) Uani 1 1 d . . . H16 H 0.4030 0.3695 -0.0153 0.093 Uiso 1 1 calc R . . C17 C 0.2638(3) 0.2826(2) -0.0680(3) 0.0807(10) Uani 1 1 d . . . H17 H 0.1993 0.3202 -0.1118 0.097 Uiso 1 1 calc R . . C18 C 0.2354(3) 0.1970(3) -0.0606(3) 0.0821(11) Uani 1 1 d . . . H18 H 0.1511 0.1769 -0.0977 0.098 Uiso 1 1 calc R . . C19 C 0.3323(3) 0.14166(19) 0.0020(3) 0.0705(10) Uani 1 1 d . . . H19 H 0.3140 0.0838 0.0057 0.085 Uiso 1 1 calc R . . N1 N 0.5141(2) 0.05966(17) 0.2187(3) 0.0717(8) Uani 1 1 d . . . N2 N 0.5498(2) 0.11232(14) 0.1275(2) 0.0587(7) Uani 1 1 d . . . O1 O 0.8907(2) -0.04577(17) 0.3436(2) 0.1151(10) Uani 1 1 d . . . O2 O 0.9259(2) 0.01921(15) 0.1649(3) 0.1002(9) 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 0.058(2) 0.060(2) 0.052(2) -0.0099(17) 0.0027(17) 0.0031(17) C2 0.064(2) 0.055(2) 0.061(2) -0.0020(17) -0.0039(18) 0.0004(17) C3 0.073(2) 0.059(2) 0.067(2) 0.0118(18) 0.003(2) -0.0012(18) C4 0.062(2) 0.058(2) 0.063(2) 0.0028(18) 0.0164(18) 0.0122(17) C5 0.073(2) 0.071(2) 0.085(3) -0.010(2) 0.026(2) -0.0025(19) C6 0.105(3) 0.075(3) 0.129(4) -0.001(3) 0.062(3) -0.005(2) C7 0.123(4) 0.100(3) 0.119(4) 0.032(3) 0.075(3) 0.028(3) C8 0.112(4) 0.142(4) 0.077(3) 0.027(3) 0.037(3) 0.035(3) C9 0.076(2) 0.102(3) 0.064(3) 0.006(2) 0.014(2) 0.0113(19) C10 0.084(3) 0.073(3) 0.070(3) 0.001(2) -0.002(2) -0.004(2) C11 0.071(3) 0.134(4) 0.168(4) 0.013(3) 0.005(3) 0.041(3) C12 0.086(3) 0.159(4) 0.236(6) -0.034(4) -0.002(3) -0.004(3) C13 0.108(3) 0.105(3) 0.109(3) 0.042(3) 0.015(2) -0.002(2) C14 0.056(2) 0.065(2) 0.051(2) -0.0008(17) 0.0070(15) -0.0017(17) C15 0.061(2) 0.072(2) 0.076(2) 0.0030(19) 0.0107(17) -0.0052(18) C16 0.083(3) 0.067(2) 0.081(3) 0.0062(19) 0.016(2) 0.008(2) C17 0.077(3) 0.084(3) 0.076(3) 0.009(2) 0.007(2) 0.015(2) C18 0.066(2) 0.089(3) 0.082(3) -0.007(2) -0.0002(19) -0.003(2) C19 0.065(2) 0.060(2) 0.078(2) -0.0057(18) 0.0022(18) 0.0012(18) N1 0.0731(19) 0.0691(17) 0.0732(19) 0.0139(15) 0.0179(15) -0.0071(15) N2 0.0530(17) 0.0582(16) 0.0621(17) 0.0026(14) 0.0083(14) 0.0025(14) O1 0.105(2) 0.124(2) 0.105(2) 0.0387(17) 0.0039(16) 0.0300(15) O2 0.0772(18) 0.1019(19) 0.116(2) 0.0222(16) 0.0108(16) 0.0306(14) _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 1.349(4) . ? C1 C2 1.388(4) . ? C1 C4 1.473(4) . ? C2 C3 1.393(4) . ? C2 C10 1.448(4) . ? C3 N1 1.321(3) . ? C3 C13 1.504(4) . ? C4 C5 1.388(4) . ? C4 C9 1.392(4) . ? C5 C6 1.372(4) . ? C5 H5 0.9300 . ? C6 C7 1.378(5) . ? C6 H6 0.9300 . ? C7 C8 1.367(5) . ? C7 H7 0.9300 . ? C8 C9 1.374(5) . ? C8 H8 0.9300 . ? C9 H9 0.9300 . ? C10 O1 1.191(4) . ? C10 O2 1.343(4) . ? C11 C12 1.404(5) . ? C11 O2 1.448(4) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 C19 1.338(4) . ? C14 C15 1.389(4) . ? C14 N2 1.434(3) . ? C15 C16 1.383(4) . ? C15 H15 0.9300 . ? C16 C17 1.344(4) . ? C16 H16 0.9300 . ? C17 C18 1.381(4) . ? C17 H17 0.9300 . ? C18 C19 1.377(4) . ? C18 H18 0.9300 . ? C19 H19 0.9300 . ? N1 N2 1.379(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 N2 C1 C2 104.9(3) . . ? N2 C1 C4 121.5(3) . . ? C2 C1 C4 133.6(3) . . ? C1 C2 C3 106.5(3) . . ? C1 C2 C10 130.7(4) . . ? C3 C2 C10 122.6(3) . . ? N1 C3 C2 111.4(3) . . ? N1 C3 C13 117.5(3) . . ? C2 C3 C13 131.1(3) . . ? C5 C4 C9 119.1(3) . . ? C5 C4 C1 120.4(3) . . ? C9 C4 C1 120.5(3) . . ? C6 C5 C4 118.6(3) . . ? C6 C5 H5 120.7 . . ? C4 C5 H5 120.7 . . ? C5 C6 C7 122.0(4) . . ? C5 C6 H6 119.0 . . ? C7 C6 H6 119.0 . . ? C8 C7 C6 119.8(4) . . ? C8 C7 H7 120.1 . . ? C6 C7 H7 120.1 . . ? C7 C8 C9 119.1(4) . . ? C7 C8 H8 120.4 . . ? C9 C8 H8 120.4 . . ? C8 C9 C4 121.4(4) . . ? C8 C9 H9 119.3 . . ? C4 C9 H9 119.3 . . ? O1 C10 O2 123.8(4) . . ? O1 C10 C2 125.0(4) . . ? O2 C10 C2 111.2(3) . . ? C12 C11 O2 111.1(3) . . ? C12 C11 H11A 109.4 . . ? O2 C11 H11A 109.4 . . ? C12 C11 H11B 109.4 . . ? O2 C11 H11B 109.4 . . ? H11A C11 H11B 108.0 . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C3 C13 H13A 109.5 . . ? C3 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C3 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C19 C14 C15 121.1(3) . . ? C19 C14 N2 118.8(3) . . ? C15 C14 N2 120.1(3) . . ? C16 C15 C14 118.0(3) . . ? C16 C15 H15 121.0 . . ? C14 C15 H15 121.0 . . ? C17 C16 C15 121.2(3) . . ? C17 C16 H16 119.4 . . ? C15 C16 H16 119.4 . . ? C16 C17 C18 119.8(3) . . ? C16 C17 H17 120.1 . . ? C18 C17 H17 120.1 . . ? C19 C18 C17 119.7(3) . . ? C19 C18 H18 120.2 . . ? C17 C18 H18 120.2 . . ? C14 C19 C18 120.2(3) . . ? C14 C19 H19 119.9 . . ? C18 C19 H19 119.9 . . ? C3 N1 N2 104.3(3) . . ? C1 N2 N1 112.8(2) . . ? C1 N2 C14 129.6(3) . . ? N1 N2 C14 117.5(3) . . ? C10 O2 C11 117.7(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 N2 C1 C2 C3 1.7(3) . . . . ? C4 C1 C2 C3 -178.0(3) . . . . ? N2 C1 C2 C10 178.3(3) . . . . ? C4 C1 C2 C10 -1.5(5) . . . . ? C1 C2 C3 N1 -1.5(3) . . . . ? C10 C2 C3 N1 -178.4(3) . . . . ? C1 C2 C3 C13 179.1(3) . . . . ? C10 C2 C3 C13 2.2(5) . . . . ? N2 C1 C4 C5 121.1(3) . . . . ? C2 C1 C4 C5 -59.2(4) . . . . ? N2 C1 C4 C9 -58.4(4) . . . . ? C2 C1 C4 C9 121.3(3) . . . . ? C9 C4 C5 C6 0.9(4) . . . . ? C1 C4 C5 C6 -178.7(3) . . . . ? C4 C5 C6 C7 0.4(5) . . . . ? C5 C6 C7 C8 -1.9(6) . . . . ? C6 C7 C8 C9 2.0(6) . . . . ? C7 C8 C9 C4 -0.8(6) . . . . ? C5 C4 C9 C8 -0.7(5) . . . . ? C1 C4 C9 C8 178.9(3) . . . . ? C1 C2 C10 O1 170.5(3) . . . . ? C3 C2 C10 O1 -13.4(5) . . . . ? C1 C2 C10 O2 -9.8(4) . . . . ? C3 C2 C10 O2 166.3(3) . . . . ? C19 C14 C15 C16 1.2(5) . . . . ? N2 C14 C15 C16 -176.8(3) . . . . ? C14 C15 C16 C17 -1.4(5) . . . . ? C15 C16 C17 C18 1.5(5) . . . . ? C16 C17 C18 C19 -1.4(5) . . . . ? C15 C14 C19 C18 -1.2(5) . . . . ? N2 C14 C19 C18 176.9(3) . . . . ? C17 C18 C19 C14 1.2(5) . . . . ? C2 C3 N1 N2 0.6(3) . . . . ? C13 C3 N1 N2 -179.9(2) . . . . ? C2 C1 N2 N1 -1.5(3) . . . . ? C4 C1 N2 N1 178.3(2) . . . . ? C2 C1 N2 C14 177.0(3) . . . . ? C4 C1 N2 C14 -3.3(4) . . . . ? C3 N1 N2 C1 0.6(3) . . . . ? C3 N1 N2 C14 -178.1(2) . . . . ? C19 C14 N2 C1 132.6(3) . . . . ? C15 C14 N2 C1 -49.2(4) . . . . ? C19 C14 N2 N1 -49.0(4) . . . . ? C15 C14 N2 N1 129.2(3) . . . . ? O1 C10 O2 C11 -4.8(5) . . . . ? C2 C10 O2 C11 175.6(3) . . . . ? C12 C11 O2 C10 -96.3(4) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.99 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.233 _refine_diff_density_min -0.188 _refine_diff_density_rms 0.042 data_2e _database_code_depnum_ccdc_archive 'CCDC 708930' _audit_creation_method SHELXTL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H19 F3 N2 O2' _chemical_formula_weight 436.42 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 P2(1)/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 12.182(2) _cell_length_b 19.321(4) _cell_length_c 9.0766(17) _cell_angle_alpha 90.00 _cell_angle_beta 98.535(4) _cell_angle_gamma 90.00 _cell_volume 2112.7(7) _cell_formula_units_Z 4 _cell_measurement_temperature 170(2) _cell_measurement_reflns_used 1635 _cell_measurement_theta_min 2.50 _cell_measurement_theta_max 22.33 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.372 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 904 _exptl_absorpt_coefficient_mu 0.106 _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 170(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11696 _diffrn_reflns_av_R_equivalents 0.0557 _diffrn_reflns_av_sigmaI/netI 0.1132 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 1.69 _diffrn_reflns_theta_max 26.00 _reflns_number_total 4139 _reflns_number_gt 1985 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0151P)^2^+0.0000P] 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 4139 _refine_ls_number_parameters 290 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0749 _refine_ls_R_factor_gt 0.0341 _refine_ls_wR_factor_ref 0.0586 _refine_ls_wR_factor_gt 0.0551 _refine_ls_goodness_of_fit_ref 0.676 _refine_ls_restrained_S_all 0.676 _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 0.42143(12) -0.00783(8) 0.23918(17) 0.0269(4) Uani 1 1 d . . . C2 C 0.52595(12) 0.01402(8) 0.21314(17) 0.0262(4) Uani 1 1 d . . . C3 C 0.59930(13) -0.04107(8) 0.26291(18) 0.0287(4) Uani 1 1 d . . . C4 C 0.31282(12) 0.02830(8) 0.22084(19) 0.0267(4) Uani 1 1 d . . . C5 C 0.28976(13) 0.07314(8) 0.33191(19) 0.0348(4) Uani 1 1 d . . . H5 H 0.3408 0.0777 0.4213 0.042 Uiso 1 1 calc R . . C6 C 0.19227(14) 0.11111(8) 0.3121(2) 0.0388(5) Uani 1 1 d . . . H6 H 0.1771 0.1423 0.3875 0.047 Uiso 1 1 calc R . . C7 C 0.11738(13) 0.10385(8) 0.1839(2) 0.0335(5) Uani 1 1 d . . . C8 C 0.13863(13) 0.05771(8) 0.07556(19) 0.0383(5) Uani 1 1 d . . . H8 H 0.0862 0.0518 -0.0120 0.046 Uiso 1 1 calc R . . C9 C 0.23633(13) 0.02005(8) 0.09460(19) 0.0346(4) Uani 1 1 d . . . H9 H 0.2507 -0.0117 0.0199 0.041 Uiso 1 1 calc R . . C10 C 0.01777(16) 0.14902(10) 0.1537(2) 0.0502(6) Uani 1 1 d . . . C11 C 0.55085(14) 0.07813(8) 0.13835(19) 0.0305(4) Uani 1 1 d . . . C12 C 0.47894(14) 0.18771(8) 0.0530(2) 0.0444(5) Uani 1 1 d . . . H12A H 0.4822 0.1785 -0.0535 0.053 Uiso 1 1 calc R . . H12B H 0.5478 0.2120 0.0965 0.053 Uiso 1 1 calc R . . C13 C 0.37908(14) 0.23078(8) 0.0697(2) 0.0583(6) Uani 1 1 d . . . H13A H 0.3117 0.2061 0.0264 0.087 Uiso 1 1 calc R . . H13B H 0.3834 0.2750 0.0180 0.087 Uiso 1 1 calc R . . H13C H 0.3769 0.2394 0.1757 0.087 Uiso 1 1 calc R . . C14 C 0.72133(13) -0.04934(8) 0.27682(18) 0.0288(4) Uani 1 1 d . . . C15 C 0.76554(13) -0.11515(8) 0.26629(19) 0.0379(5) Uani 1 1 d . . . H15 H 0.7172 -0.1534 0.2425 0.045 Uiso 1 1 calc R . . C16 C 0.87861(14) -0.12555(10) 0.2899(2) 0.0469(5) Uani 1 1 d . . . H16 H 0.9076 -0.1708 0.2816 0.056 Uiso 1 1 calc R . . C17 C 0.95017(14) -0.07062(10) 0.3255(2) 0.0466(5) Uani 1 1 d . . . H17 H 1.0282 -0.0779 0.3427 0.056 Uiso 1 1 calc R . . C18 C 0.90699(13) -0.00500(9) 0.33558(18) 0.0418(5) Uani 1 1 d . . . H18 H 0.9557 0.0331 0.3590 0.050 Uiso 1 1 calc R . . C19 C 0.79367(13) 0.00565(9) 0.31188(18) 0.0347(4) Uani 1 1 d . . . H19 H 0.7650 0.0510 0.3197 0.042 Uiso 1 1 calc R . . C20 C 0.35647(13) -0.11804(8) 0.3481(2) 0.0280(4) Uani 1 1 d . . . C21 C 0.26654(13) -0.14078(8) 0.2516(2) 0.0369(5) Uani 1 1 d . . . H21 H 0.2554 -0.1261 0.1506 0.044 Uiso 1 1 calc R . . C22 C 0.19217(14) -0.18546(8) 0.3036(2) 0.0423(5) Uani 1 1 d . . . H22 H 0.1290 -0.2013 0.2381 0.051 Uiso 1 1 calc R . . C23 C 0.20920(15) -0.20697(8) 0.4493(2) 0.0428(5) Uani 1 1 d . . . H23 H 0.1574 -0.2372 0.4847 0.051 Uiso 1 1 calc R . . C24 C 0.30126(15) -0.18489(8) 0.5444(2) 0.0440(5) Uani 1 1 d . . . H24 H 0.3134 -0.2005 0.6448 0.053 Uiso 1 1 calc R . . C25 C 0.37601(13) -0.14001(8) 0.4940(2) 0.0360(5) Uani 1 1 d . . . H25 H 0.4397 -0.1246 0.5589 0.043 Uiso 1 1 calc R . . F1 F -0.06937(8) 0.11876(5) 0.07527(14) 0.0703(4) Uani 1 1 d . . . F2 F -0.01637(9) 0.17234(6) 0.27744(14) 0.0863(4) Uani 1 1 d . . . F3 F 0.03729(9) 0.20557(6) 0.07641(15) 0.0810(4) Uani 1 1 d . . . N1 N 0.43624(10) -0.07213(6) 0.29780(14) 0.0295(4) Uani 1 1 d . . . N2 N 0.54415(10) -0.09326(6) 0.31487(15) 0.0315(4) Uani 1 1 d . . . O1 O 0.63517(9) 0.09023(5) 0.08833(13) 0.0402(3) Uani 1 1 d . . . O2 O 0.46719(9) 0.12354(5) 0.13156(13) 0.0399(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 0.0279(10) 0.0247(10) 0.0279(11) 0.0004(9) 0.0037(8) 0.0011(8) C2 0.0260(10) 0.0212(10) 0.0320(11) -0.0012(8) 0.0063(8) 0.0005(8) C3 0.0284(10) 0.0274(10) 0.0308(11) -0.0025(8) 0.0063(9) -0.0023(8) C4 0.0247(10) 0.0245(10) 0.0315(11) 0.0026(8) 0.0065(9) -0.0017(8) C5 0.0294(11) 0.0410(11) 0.0327(12) -0.0032(9) 0.0009(9) 0.0013(9) C6 0.0355(11) 0.0382(12) 0.0437(14) -0.0084(10) 0.0089(10) 0.0058(9) C7 0.0264(11) 0.0319(11) 0.0427(13) 0.0016(9) 0.0068(10) 0.0022(8) C8 0.0362(11) 0.0428(12) 0.0334(13) 0.0000(10) -0.0030(9) 0.0042(9) C9 0.0341(11) 0.0332(11) 0.0359(12) -0.0037(9) 0.0038(10) 0.0054(9) C10 0.0404(13) 0.0450(14) 0.0642(17) 0.0013(12) 0.0045(12) 0.0090(11) C11 0.0300(11) 0.0271(11) 0.0338(12) -0.0047(9) 0.0030(9) 0.0021(9) C12 0.0486(12) 0.0289(11) 0.0566(14) 0.0125(10) 0.0109(11) 0.0014(9) C13 0.0636(14) 0.0360(12) 0.0763(17) 0.0081(11) 0.0140(13) 0.0156(10) C14 0.0247(10) 0.0307(11) 0.0312(12) 0.0044(8) 0.0053(8) 0.0010(8) C15 0.0339(11) 0.0322(11) 0.0490(13) 0.0035(9) 0.0106(10) 0.0023(9) C16 0.0409(12) 0.0449(13) 0.0563(15) 0.0067(11) 0.0121(11) 0.0140(10) C17 0.0262(11) 0.0641(14) 0.0500(14) 0.0056(12) 0.0076(10) 0.0084(11) C18 0.0297(11) 0.0509(13) 0.0442(13) 0.0017(10) 0.0036(9) -0.0067(9) C19 0.0324(11) 0.0334(11) 0.0383(12) -0.0009(9) 0.0051(9) 0.0010(9) C20 0.0242(10) 0.0208(10) 0.0403(13) 0.0002(9) 0.0093(9) -0.0013(8) C21 0.0343(11) 0.0355(11) 0.0408(13) 0.0042(9) 0.0054(10) -0.0029(9) C22 0.0304(11) 0.0421(12) 0.0539(15) -0.0028(11) 0.0045(10) -0.0088(9) C23 0.0431(12) 0.0361(12) 0.0525(15) -0.0020(11) 0.0180(11) -0.0139(9) C24 0.0565(13) 0.0402(12) 0.0374(13) 0.0020(10) 0.0140(11) -0.0128(10) C25 0.0368(11) 0.0313(11) 0.0399(13) -0.0039(9) 0.0059(10) -0.0087(9) F1 0.0335(7) 0.0661(8) 0.1056(10) -0.0059(7) -0.0090(7) 0.0102(6) F2 0.0711(9) 0.1046(10) 0.0847(10) -0.0178(8) 0.0165(8) 0.0531(7) F3 0.0588(8) 0.0496(8) 0.1348(12) 0.0339(8) 0.0147(8) 0.0189(6) N1 0.0253(8) 0.0272(8) 0.0369(10) 0.0031(7) 0.0071(7) 0.0003(7) N2 0.0235(8) 0.0286(8) 0.0430(10) 0.0033(7) 0.0068(7) 0.0022(7) O1 0.0340(7) 0.0370(8) 0.0535(9) 0.0069(6) 0.0197(7) 0.0006(6) O2 0.0377(7) 0.0253(7) 0.0594(9) 0.0137(6) 0.0165(7) 0.0058(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 N1 1.3529(17) . ? C1 C2 1.3945(18) . ? C1 C4 1.4833(19) . ? C2 C3 1.420(2) . ? C2 C11 1.466(2) . ? C3 N2 1.3360(16) . ? C3 C14 1.482(2) . ? C4 C9 1.375(2) . ? C4 C5 1.389(2) . ? C5 C6 1.385(2) . ? C5 H5 0.9500 . ? C6 C7 1.376(2) . ? C6 H6 0.9500 . ? C7 C8 1.380(2) . ? C7 C10 1.487(2) . ? C8 C9 1.384(2) . ? C8 H8 0.9500 . ? C9 H9 0.9500 . ? C10 F1 1.323(2) . ? C10 F2 1.333(2) . ? C10 F3 1.3387(19) . ? C11 O1 1.2059(16) . ? C11 O2 1.3393(17) . ? C12 O2 1.4476(16) . ? C12 C13 1.500(2) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 C19 1.387(2) . ? C14 C15 1.3897(19) . ? C15 C16 1.377(2) . ? C15 H15 0.9500 . ? C16 C17 1.381(2) . ? C16 H16 0.9500 . ? C17 C18 1.381(2) . ? C17 H17 0.9500 . ? C18 C19 1.381(2) . ? C18 H18 0.9500 . ? C19 H19 0.9500 . ? C20 C21 1.370(2) . ? C20 C25 1.377(2) . ? C20 N1 1.4393(17) . ? C21 C22 1.3841(19) . ? C21 H21 0.9500 . ? C22 C23 1.372(2) . ? C22 H22 0.9500 . ? C23 C24 1.378(2) . ? C23 H23 0.9500 . ? C24 C25 1.3836(19) . ? C24 H24 0.9500 . ? C25 H25 0.9500 . ? N1 N2 1.3633(15) . ? 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 N1 C1 C2 105.84(13) . . ? N1 C1 C4 122.75(13) . . ? C2 C1 C4 131.30(14) . . ? C1 C2 C3 105.45(14) . . ? C1 C2 C11 126.26(15) . . ? C3 C2 C11 128.11(14) . . ? N2 C3 C2 110.65(13) . . ? N2 C3 C14 116.05(14) . . ? C2 C3 C14 133.16(15) . . ? C9 C4 C5 119.48(15) . . ? C9 C4 C1 121.46(15) . . ? C5 C4 C1 119.02(16) . . ? C6 C5 C4 119.89(17) . . ? C6 C5 H5 120.1 . . ? C4 C5 H5 120.1 . . ? C7 C6 C5 120.26(16) . . ? C7 C6 H6 119.9 . . ? C5 C6 H6 119.9 . . ? C6 C7 C8 119.86(15) . . ? C6 C7 C10 121.10(17) . . ? C8 C7 C10 118.85(18) . . ? C7 C8 C9 119.98(17) . . ? C7 C8 H8 120.0 . . ? C9 C8 H8 120.0 . . ? C4 C9 C8 120.47(16) . . ? C4 C9 H9 119.8 . . ? C8 C9 H9 119.8 . . ? F1 C10 F2 106.08(16) . . ? F1 C10 F3 105.63(17) . . ? F2 C10 F3 105.52(16) . . ? F1 C10 C7 114.03(16) . . ? F2 C10 C7 113.05(18) . . ? F3 C10 C7 111.84(15) . . ? O1 C11 O2 122.72(15) . . ? O1 C11 C2 125.78(15) . . ? O2 C11 C2 111.50(14) . . ? O2 C12 C13 106.53(12) . . ? O2 C12 H12A 110.4 . . ? C13 C12 H12A 110.4 . . ? O2 C12 H12B 110.4 . . ? C13 C12 H12B 110.4 . . ? H12A C12 H12B 108.6 . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C19 C14 C15 118.50(15) . . ? C19 C14 C3 122.15(15) . . ? C15 C14 C3 119.14(15) . . ? C16 C15 C14 120.78(16) . . ? C16 C15 H15 119.6 . . ? C14 C15 H15 119.6 . . ? C15 C16 C17 120.43(17) . . ? C15 C16 H16 119.8 . . ? C17 C16 H16 119.8 . . ? C18 C17 C16 119.18(17) . . ? C18 C17 H17 120.4 . . ? C16 C17 H17 120.4 . . ? C19 C18 C17 120.56(16) . . ? C19 C18 H18 119.7 . . ? C17 C18 H18 119.7 . . ? C18 C19 C14 120.54(16) . . ? C18 C19 H19 119.7 . . ? C14 C19 H19 119.7 . . ? C21 C20 C25 121.60(15) . . ? C21 C20 N1 120.54(16) . . ? C25 C20 N1 117.82(15) . . ? C20 C21 C22 118.93(17) . . ? C20 C21 H21 120.5 . . ? C22 C21 H21 120.5 . . ? C23 C22 C21 120.30(17) . . ? C23 C22 H22 119.9 . . ? C21 C22 H22 119.9 . . ? C22 C23 C24 120.18(16) . . ? C22 C23 H23 119.9 . . ? C24 C23 H23 119.9 . . ? C23 C24 C25 120.09(17) . . ? C23 C24 H24 120.0 . . ? C25 C24 H24 120.0 . . ? C20 C25 C24 118.87(17) . . ? C20 C25 H25 120.6 . . ? C24 C25 H25 120.6 . . ? C1 N1 N2 112.94(12) . . ? C1 N1 C20 129.33(13) . . ? N2 N1 C20 117.67(12) . . ? C3 N2 N1 105.11(12) . . ? C11 O2 C12 116.97(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 N1 C1 C2 C3 -1.01(17) . . . . ? C4 C1 C2 C3 175.19(17) . . . . ? N1 C1 C2 C11 174.38(15) . . . . ? C4 C1 C2 C11 -9.4(3) . . . . ? C1 C2 C3 N2 0.40(18) . . . . ? C11 C2 C3 N2 -174.87(15) . . . . ? C1 C2 C3 C14 -174.96(17) . . . . ? C11 C2 C3 C14 9.8(3) . . . . ? N1 C1 C4 C9 -87.9(2) . . . . ? C2 C1 C4 C9 96.5(2) . . . . ? N1 C1 C4 C5 94.24(19) . . . . ? C2 C1 C4 C5 -81.4(2) . . . . ? C9 C4 C5 C6 -2.6(2) . . . . ? C1 C4 C5 C6 175.38(14) . . . . ? C4 C5 C6 C7 1.0(2) . . . . ? C5 C6 C7 C8 1.1(2) . . . . ? C5 C6 C7 C10 -173.88(16) . . . . ? C6 C7 C8 C9 -1.5(2) . . . . ? C10 C7 C8 C9 173.56(15) . . . . ? C5 C4 C9 C8 2.1(2) . . . . ? C1 C4 C9 C8 -175.75(14) . . . . ? C7 C8 C9 C4 -0.1(2) . . . . ? C6 C7 C10 F1 -148.71(17) . . . . ? C8 C7 C10 F1 36.3(2) . . . . ? C6 C7 C10 F2 -27.4(2) . . . . ? C8 C7 C10 F2 157.57(16) . . . . ? C6 C7 C10 F3 91.5(2) . . . . ? C8 C7 C10 F3 -83.5(2) . . . . ? C1 C2 C11 O1 -163.38(17) . . . . ? C3 C2 C11 O1 11.0(3) . . . . ? C1 C2 C11 O2 16.8(2) . . . . ? C3 C2 C11 O2 -168.87(16) . . . . ? N2 C3 C14 C19 -141.99(16) . . . . ? C2 C3 C14 C19 33.2(3) . . . . ? N2 C3 C14 C15 32.7(2) . . . . ? C2 C3 C14 C15 -152.09(18) . . . . ? C19 C14 C15 C16 -0.1(2) . . . . ? C3 C14 C15 C16 -175.03(15) . . . . ? C14 C15 C16 C17 0.4(3) . . . . ? C15 C16 C17 C18 -0.7(3) . . . . ? C16 C17 C18 C19 0.6(3) . . . . ? C17 C18 C19 C14 -0.3(3) . . . . ? C15 C14 C19 C18 0.0(2) . . . . ? C3 C14 C19 C18 174.81(15) . . . . ? C25 C20 C21 C22 1.8(2) . . . . ? N1 C20 C21 C22 179.34(13) . . . . ? C20 C21 C22 C23 -0.6(2) . . . . ? C21 C22 C23 C24 -0.8(3) . . . . ? C22 C23 C24 C25 1.1(3) . . . . ? C21 C20 C25 C24 -1.5(2) . . . . ? N1 C20 C25 C24 -179.15(13) . . . . ? C23 C24 C25 C20 0.1(2) . . . . ? C2 C1 N1 N2 1.33(18) . . . . ? C4 C1 N1 N2 -175.28(14) . . . . ? C2 C1 N1 C20 178.55(15) . . . . ? C4 C1 N1 C20 1.9(3) . . . . ? C21 C20 N1 C1 60.7(2) . . . . ? C25 C20 N1 C1 -121.69(18) . . . . ? C21 C20 N1 N2 -122.23(16) . . . . ? C25 C20 N1 N2 55.43(19) . . . . ? C2 C3 N2 N1 0.37(17) . . . . ? C14 C3 N2 N1 176.60(13) . . . . ? C1 N1 N2 C3 -1.07(17) . . . . ? C20 N1 N2 C3 -178.65(13) . . . . ? O1 C11 O2 C12 3.4(2) . . . . ? C2 C11 O2 C12 -176.78(13) . . . . ? C13 C12 O2 C11 -176.48(15) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.159 _refine_diff_density_min -0.167 _refine_diff_density_rms 0.032 data_2f _database_code_depnum_ccdc_archive 'CCDC 708931' _audit_creation_method SHELXTL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H19 F3 N2 O2' _chemical_formula_weight 436.42 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 9.801(2) _cell_length_b 9.982(2) _cell_length_c 12.377(3) _cell_angle_alpha 78.875(5) _cell_angle_beta 88.801(5) _cell_angle_gamma 64.005(4) _cell_volume 1065.2(4) _cell_formula_units_Z 2 _cell_measurement_temperature 170(2) _cell_measurement_reflns_used 470 _cell_measurement_theta_min 2.32 _cell_measurement_theta_max 20.15 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.361 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 452 _exptl_absorpt_coefficient_mu 0.105 _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 170(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5963 _diffrn_reflns_av_R_equivalents 0.1207 _diffrn_reflns_av_sigmaI/netI 0.3516 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.68 _diffrn_reflns_theta_max 26.00 _reflns_number_total 4052 _reflns_number_gt 2041 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0411P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0067(14) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4052 _refine_ls_number_parameters 291 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2089 _refine_ls_R_factor_gt 0.0684 _refine_ls_wR_factor_ref 0.1613 _refine_ls_wR_factor_gt 0.1151 _refine_ls_goodness_of_fit_ref 0.714 _refine_ls_restrained_S_all 0.714 _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 1.0171(5) 0.7811(5) -0.0733(4) 0.0417(14) Uani 1 1 d . . . C2 C 1.0300(5) 0.7005(5) 0.0346(4) 0.0379(13) Uani 1 1 d . . . C3 C 0.8955(5) 0.7918(5) 0.0818(4) 0.0335(12) Uani 1 1 d . . . C4 C 1.1241(5) 0.7461(5) -0.1602(4) 0.0416(14) Uani 1 1 d . . . C5 C 1.1852(5) 0.8458(5) -0.2036(4) 0.0407(13) Uani 1 1 d . . . H5 H 1.1594 0.9357 -0.1759 0.049 Uiso 1 1 calc R . . C6 C 1.2825(5) 0.8141(5) -0.2860(4) 0.0450(14) Uani 1 1 d . . . H6 H 1.3245 0.8822 -0.3144 0.054 Uiso 1 1 calc R . . C7 C 1.3211(5) 0.6850(5) -0.3291(4) 0.0447(13) Uani 1 1 d . . . H7 H 1.3877 0.6650 -0.3871 0.054 Uiso 1 1 calc R . . C8 C 1.2607(5) 0.5859(6) -0.2861(4) 0.0502(15) Uani 1 1 d . . . H8 H 1.2874 0.4958 -0.3137 0.060 Uiso 1 1 calc R . . C9 C 1.1628(5) 0.6168(5) -0.2042(4) 0.0445(14) Uani 1 1 d . . . H9 H 1.1204 0.5488 -0.1767 0.053 Uiso 1 1 calc R . . C10 C 1.1487(6) 0.5527(6) 0.0859(4) 0.0398(14) Uani 1 1 d . . . C11 C 1.4140(5) 0.3852(5) 0.0955(4) 0.0532(15) Uani 1 1 d . . . H11A H 1.3978 0.3488 0.1727 0.064 Uiso 1 1 calc R . . H11B H 1.5096 0.3962 0.0958 0.064 Uiso 1 1 calc R . . C12 C 1.4280(6) 0.2715(5) 0.0283(4) 0.0628(16) Uani 1 1 d . . . H12A H 1.3425 0.2456 0.0398 0.094 Uiso 1 1 calc R . . H12B H 1.5239 0.1795 0.0509 0.094 Uiso 1 1 calc R . . H12C H 1.4269 0.3148 -0.0500 0.094 Uiso 1 1 calc R . . C13 C 0.8465(5) 0.7732(5) 0.1964(4) 0.0372(12) Uani 1 1 d . . . C14 C 0.9491(6) 0.7038(5) 0.2877(4) 0.0489(14) Uani 1 1 d . . . H14 H 1.0550 0.6613 0.2774 0.059 Uiso 1 1 calc R . . C15 C 0.9023(6) 0.6945(5) 0.3930(4) 0.0472(14) Uani 1 1 d . . . H15 H 0.9743 0.6474 0.4551 0.057 Uiso 1 1 calc R . . C16 C 0.7479(6) 0.7552(5) 0.4067(4) 0.0413(13) Uani 1 1 d . . . C17 C 0.6428(6) 0.8268(5) 0.3175(4) 0.0461(14) Uani 1 1 d . . . H17 H 0.5369 0.8702 0.3280 0.055 Uiso 1 1 calc R . . C18 C 0.6930(5) 0.8346(5) 0.2123(4) 0.0396(13) Uani 1 1 d . . . H18 H 0.6209 0.8830 0.1502 0.047 Uiso 1 1 calc R . . C19 C 0.7012(7) 0.7369(7) 0.5189(5) 0.0630(17) Uani 1 1 d . . . C20 C 0.8155(5) 1.0304(5) -0.1796(4) 0.0389(13) Uani 1 1 d . . . C21 C 0.7409(5) 1.1762(5) -0.1637(4) 0.0385(12) Uani 1 1 d . . . H21 H 0.7344 1.1962 -0.0913 0.046 Uiso 1 1 calc R . . C22 C 0.6749(5) 1.2948(5) -0.2540(4) 0.0436(13) Uani 1 1 d . . . H22 H 0.6218 1.3968 -0.2442 0.052 Uiso 1 1 calc R . . C23 C 0.6873(5) 1.2630(6) -0.3585(4) 0.0503(15) Uani 1 1 d . . . H23 H 0.6441 1.3439 -0.4209 0.060 Uiso 1 1 calc R . . C24 C 0.7609(5) 1.1163(6) -0.3729(4) 0.0496(15) Uani 1 1 d . . . H24 H 0.7691 1.0964 -0.4454 0.060 Uiso 1 1 calc R . . C25 C 0.8236(5) 0.9965(5) -0.2834(4) 0.0421(13) Uani 1 1 d . . . H25 H 0.8709 0.8941 -0.2928 0.050 Uiso 1 1 calc R . . F1 F 0.6931(4) 0.6057(4) 0.5555(3) 0.0981(12) Uani 1 1 d . . . F2 F 0.7865(5) 0.7405(6) 0.5961(3) 0.144(2) Uani 1 1 d . . . F3 F 0.5587(5) 0.8352(4) 0.5354(3) 0.1179(15) Uani 1 1 d . . . N1 N 0.8845(4) 0.9079(4) -0.0842(3) 0.0410(11) Uani 1 1 d . . . N2 N 0.8090(4) 0.9206(4) 0.0098(3) 0.0401(11) Uani 1 1 d . . . O1 O 1.1325(4) 0.4565(4) 0.1527(3) 0.0603(11) Uani 1 1 d . . . O2 O 1.2874(3) 0.5323(3) 0.0510(2) 0.0423(9) 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 0.018(3) 0.034(3) 0.068(4) -0.023(3) -0.008(3) -0.002(2) C2 0.037(3) 0.036(3) 0.040(3) -0.002(3) -0.012(3) -0.017(3) C3 0.024(3) 0.038(3) 0.039(3) -0.010(3) 0.001(3) -0.014(3) C4 0.034(3) 0.031(3) 0.054(4) -0.021(3) -0.012(3) -0.003(3) C5 0.031(3) 0.041(3) 0.057(4) -0.024(3) 0.006(3) -0.017(3) C6 0.038(3) 0.040(3) 0.055(4) -0.007(3) -0.007(3) -0.016(3) C7 0.047(3) 0.053(4) 0.033(3) -0.011(3) 0.003(3) -0.020(3) C8 0.047(3) 0.040(3) 0.066(4) -0.027(3) 0.002(3) -0.014(3) C9 0.041(3) 0.038(3) 0.060(4) -0.016(3) -0.002(3) -0.019(3) C10 0.041(3) 0.036(3) 0.038(3) -0.010(3) -0.010(3) -0.012(3) C11 0.037(3) 0.035(3) 0.072(4) 0.000(3) -0.023(3) -0.005(3) C12 0.065(4) 0.054(4) 0.066(4) -0.023(3) 0.000(3) -0.018(3) C13 0.034(3) 0.039(3) 0.039(3) -0.014(2) 0.003(3) -0.015(3) C14 0.049(3) 0.043(3) 0.051(4) -0.007(3) -0.009(3) -0.017(3) C15 0.058(4) 0.055(4) 0.031(3) -0.007(3) 0.000(3) -0.028(3) C16 0.058(4) 0.045(3) 0.029(3) -0.012(2) 0.012(3) -0.029(3) C17 0.042(3) 0.055(4) 0.048(4) -0.016(3) 0.012(3) -0.026(3) C18 0.047(3) 0.037(3) 0.037(3) -0.009(2) 0.004(3) -0.020(3) C19 0.086(5) 0.065(4) 0.053(4) -0.037(3) 0.028(4) -0.038(4) C20 0.027(3) 0.037(3) 0.049(4) -0.009(3) -0.012(3) -0.010(3) C21 0.031(3) 0.034(3) 0.047(3) -0.012(3) -0.003(3) -0.010(3) C22 0.038(3) 0.037(3) 0.055(4) -0.012(3) -0.003(3) -0.014(3) C23 0.052(4) 0.046(4) 0.048(4) 0.003(3) -0.022(3) -0.022(3) C24 0.052(3) 0.054(4) 0.033(3) -0.011(3) -0.002(3) -0.014(3) C25 0.039(3) 0.035(3) 0.055(4) -0.012(3) -0.004(3) -0.016(3) F1 0.148(3) 0.074(3) 0.082(3) -0.017(2) 0.038(2) -0.059(3) F2 0.187(5) 0.279(6) 0.063(3) -0.069(3) 0.028(3) -0.177(5) F3 0.124(3) 0.096(3) 0.074(3) -0.015(2) 0.047(3) 0.002(3) N1 0.035(3) 0.041(3) 0.047(3) -0.022(2) -0.003(2) -0.010(2) N2 0.037(2) 0.043(3) 0.040(3) -0.021(2) 0.003(2) -0.013(2) O1 0.053(2) 0.037(2) 0.077(3) 0.006(2) -0.006(2) -0.015(2) O2 0.033(2) 0.036(2) 0.051(2) -0.0044(16) -0.0054(18) -0.0104(17) _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 N1 1.346(5) . ? C1 C2 1.396(6) . ? C1 C4 1.468(6) . ? C2 C3 1.425(6) . ? C2 C10 1.449(6) . ? C3 N2 1.341(5) . ? C3 C13 1.492(6) . ? C4 C5 1.393(6) . ? C4 C9 1.393(5) . ? C5 C6 1.367(6) . ? C5 H5 0.9500 . ? C6 C7 1.384(6) . ? C6 H6 0.9500 . ? C7 C8 1.381(6) . ? C7 H7 0.9500 . ? C8 C9 1.365(6) . ? C8 H8 0.9500 . ? C9 H9 0.9500 . ? C10 O1 1.206(5) . ? C10 O2 1.357(6) . ? C11 O2 1.456(5) . ? C11 C12 1.490(6) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 C14 1.379(5) . ? C13 C18 1.380(6) . ? C14 C15 1.373(6) . ? C14 H14 0.9500 . ? C15 C16 1.382(6) . ? C15 H15 0.9500 . ? C16 C17 1.374(6) . ? C16 C19 1.456(7) . ? C17 C18 1.382(6) . ? C17 H17 0.9500 . ? C18 H18 0.9500 . ? C19 F2 1.299(5) . ? C19 F1 1.337(6) . ? C19 F3 1.349(6) . ? C20 C21 1.365(6) . ? C20 C25 1.382(6) . ? C20 N1 1.448(5) . ? C21 C22 1.385(6) . ? C21 H21 0.9500 . ? C22 C23 1.380(6) . ? C22 H22 0.9500 . ? C23 C24 1.366(6) . ? C23 H23 0.9500 . ? C24 C25 1.382(6) . ? C24 H24 0.9500 . ? C25 H25 0.9500 . ? N1 N2 1.362(5) . ? 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 N1 C1 C2 106.2(5) . . ? N1 C1 C4 124.1(5) . . ? C2 C1 C4 129.7(4) . . ? C1 C2 C3 104.7(4) . . ? C1 C2 C10 128.0(5) . . ? C3 C2 C10 127.2(5) . . ? N2 C3 C2 111.2(4) . . ? N2 C3 C13 117.7(4) . . ? C2 C3 C13 130.9(4) . . ? C5 C4 C9 118.3(5) . . ? C5 C4 C1 120.2(4) . . ? C9 C4 C1 121.5(5) . . ? C6 C5 C4 119.9(5) . . ? C6 C5 H5 120.0 . . ? C4 C5 H5 120.0 . . ? C5 C6 C7 121.5(5) . . ? C5 C6 H6 119.3 . . ? C7 C6 H6 119.3 . . ? C8 C7 C6 118.7(5) . . ? C8 C7 H7 120.7 . . ? C6 C7 H7 120.7 . . ? C9 C8 C7 120.3(5) . . ? C9 C8 H8 119.8 . . ? C7 C8 H8 119.8 . . ? C8 C9 C4 121.2(5) . . ? C8 C9 H9 119.4 . . ? C4 C9 H9 119.4 . . ? O1 C10 O2 121.8(5) . . ? O1 C10 C2 126.4(5) . . ? O2 C10 C2 111.8(5) . . ? O2 C11 C12 110.7(4) . . ? O2 C11 H11A 109.5 . . ? C12 C11 H11A 109.5 . . ? O2 C11 H11B 109.5 . . ? C12 C11 H11B 109.5 . . ? H11A C11 H11B 108.1 . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C14 C13 C18 118.6(5) . . ? C14 C13 C3 122.3(4) . . ? C18 C13 C3 118.9(4) . . ? C15 C14 C13 121.7(5) . . ? C15 C14 H14 119.1 . . ? C13 C14 H14 119.1 . . ? C14 C15 C16 118.5(5) . . ? C14 C15 H15 120.8 . . ? C16 C15 H15 120.8 . . ? C17 C16 C15 121.2(5) . . ? C17 C16 C19 121.4(5) . . ? C15 C16 C19 117.4(5) . . ? C16 C17 C18 119.2(5) . . ? C16 C17 H17 120.4 . . ? C18 C17 H17 120.4 . . ? C13 C18 C17 120.8(5) . . ? C13 C18 H18 119.6 . . ? C17 C18 H18 119.6 . . ? F2 C19 F1 103.1(5) . . ? F2 C19 F3 104.6(5) . . ? F1 C19 F3 99.3(5) . . ? F2 C19 C16 116.9(5) . . ? F1 C19 C16 114.3(4) . . ? F3 C19 C16 116.3(5) . . ? C21 C20 C25 121.9(4) . . ? C21 C20 N1 118.7(4) . . ? C25 C20 N1 119.4(4) . . ? C20 C21 C22 119.4(5) . . ? C20 C21 H21 120.3 . . ? C22 C21 H21 120.3 . . ? C23 C22 C21 119.2(5) . . ? C23 C22 H22 120.4 . . ? C21 C22 H22 120.4 . . ? C24 C23 C22 120.7(5) . . ? C24 C23 H23 119.7 . . ? C22 C23 H23 119.7 . . ? C23 C24 C25 120.8(5) . . ? C23 C24 H24 119.6 . . ? C25 C24 H24 119.6 . . ? C24 C25 C20 117.9(5) . . ? C24 C25 H25 121.0 . . ? C20 C25 H25 121.0 . . ? C1 N1 N2 113.6(4) . . ? C1 N1 C20 129.1(5) . . ? N2 N1 C20 117.3(4) . . ? C3 N2 N1 104.3(4) . . ? C10 O2 C11 116.1(4) . . ? 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 N1 C1 C2 C3 0.0(5) . . . . ? C4 C1 C2 C3 177.4(4) . . . . ? N1 C1 C2 C10 176.8(4) . . . . ? C4 C1 C2 C10 -5.8(8) . . . . ? C1 C2 C3 N2 -1.8(5) . . . . ? C10 C2 C3 N2 -178.6(4) . . . . ? C1 C2 C3 C13 -175.5(4) . . . . ? C10 C2 C3 C13 7.7(8) . . . . ? N1 C1 C4 C5 58.4(6) . . . . ? C2 C1 C4 C5 -118.6(6) . . . . ? N1 C1 C4 C9 -119.2(5) . . . . ? C2 C1 C4 C9 63.8(6) . . . . ? C9 C4 C5 C6 -1.0(6) . . . . ? C1 C4 C5 C6 -178.7(4) . . . . ? C4 C5 C6 C7 0.8(6) . . . . ? C5 C6 C7 C8 -0.8(6) . . . . ? C6 C7 C8 C9 1.2(7) . . . . ? C7 C8 C9 C4 -1.5(7) . . . . ? C5 C4 C9 C8 1.4(6) . . . . ? C1 C4 C9 C8 179.1(4) . . . . ? C1 C2 C10 O1 -144.2(5) . . . . ? C3 C2 C10 O1 31.8(8) . . . . ? C1 C2 C10 O2 36.5(6) . . . . ? C3 C2 C10 O2 -147.5(4) . . . . ? N2 C3 C13 C14 -142.9(4) . . . . ? C2 C3 C13 C14 30.4(7) . . . . ? N2 C3 C13 C18 33.5(6) . . . . ? C2 C3 C13 C18 -153.1(5) . . . . ? C18 C13 C14 C15 0.1(7) . . . . ? C3 C13 C14 C15 176.6(5) . . . . ? C13 C14 C15 C16 0.8(7) . . . . ? C14 C15 C16 C17 -1.6(7) . . . . ? C14 C15 C16 C19 176.9(4) . . . . ? C15 C16 C17 C18 1.6(7) . . . . ? C19 C16 C17 C18 -176.8(5) . . . . ? C14 C13 C18 C17 -0.1(7) . . . . ? C3 C13 C18 C17 -176.7(4) . . . . ? C16 C17 C18 C13 -0.7(7) . . . . ? C17 C16 C19 F2 -147.1(5) . . . . ? C15 C16 C19 F2 34.5(8) . . . . ? C17 C16 C19 F1 92.4(6) . . . . ? C15 C16 C19 F1 -86.0(6) . . . . ? C17 C16 C19 F3 -22.6(7) . . . . ? C15 C16 C19 F3 159.0(5) . . . . ? C25 C20 C21 C22 -1.9(7) . . . . ? N1 C20 C21 C22 179.7(4) . . . . ? C20 C21 C22 C23 -0.6(7) . . . . ? C21 C22 C23 C24 1.3(7) . . . . ? C22 C23 C24 C25 0.5(8) . . . . ? C23 C24 C25 C20 -2.9(8) . . . . ? C21 C20 C25 C24 3.6(7) . . . . ? N1 C20 C25 C24 -178.0(5) . . . . ? C2 C1 N1 N2 1.8(5) . . . . ? C4 C1 N1 N2 -175.8(4) . . . . ? C2 C1 N1 C20 -179.6(4) . . . . ? C4 C1 N1 C20 2.8(7) . . . . ? C21 C20 N1 C1 -141.8(5) . . . . ? C25 C20 N1 C1 39.7(7) . . . . ? C21 C20 N1 N2 36.8(6) . . . . ? C25 C20 N1 N2 -141.7(4) . . . . ? C2 C3 N2 N1 2.8(5) . . . . ? C13 C3 N2 N1 177.4(3) . . . . ? C1 N1 N2 C3 -2.9(5) . . . . ? C20 N1 N2 C3 178.4(4) . . . . ? O1 C10 O2 C11 2.4(7) . . . . ? C2 C10 O2 C11 -178.3(4) . . . . ? C12 C11 O2 C10 85.9(5) . . . . ? _diffrn_measured_fraction_theta_max 0.968 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.968 _refine_diff_density_max 0.345 _refine_diff_density_min -0.398 _refine_diff_density_rms 0.078