data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Yong-Ming Wu' _publ_contact_author_email ymwu@sioc.ac.cn _publ_author_name 'Yong-Ming Wu' data_cd201272 _database_code_depnum_ccdc_archive 'CCDC 784283' #TrackingRef 'cd201272.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H10 F4 N2' _chemical_formula_weight 318.27 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.7404(12) _cell_length_b 8.9622(12) _cell_length_c 9.2170(12) _cell_angle_alpha 91.509(2) _cell_angle_beta 91.580(2) _cell_angle_gamma 112.259(2) _cell_volume 667.41(15) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1741 _cell_measurement_theta_min 4.915 _cell_measurement_theta_max 56.290 _exptl_crystal_description prismatic _exptl_crystal_colour colorless _exptl_crystal_size_max 0.425 _exptl_crystal_size_mid 0.388 _exptl_crystal_size_min 0.327 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.584 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 324 _exptl_absorpt_coefficient_mu 0.134 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.7576 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details sadabs _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 3632 _diffrn_reflns_av_R_equivalents 0.0160 _diffrn_reflns_av_sigmaI/netI 0.0235 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.21 _diffrn_reflns_theta_max 26.00 _reflns_number_total 2570 _reflns_number_gt 2016 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.0842P)^2^+0.0337P] 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 0.011(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2570 _refine_ls_number_parameters 210 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0603 _refine_ls_R_factor_gt 0.0502 _refine_ls_wR_factor_ref 0.1414 _refine_ls_wR_factor_gt 0.1339 _refine_ls_goodness_of_fit_ref 1.059 _refine_ls_restrained_S_all 1.059 _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 F1 F 0.26395(18) -0.00924(16) 0.40267(16) 0.0879(5) Uani 1 1 d . . . F2 F 0.45628(16) 0.90893(13) 0.77950(14) 0.0718(4) Uani 1 1 d . . . F3 F 0.29729(15) 0.77200(15) 0.94104(12) 0.0671(4) Uani 1 1 d . . . F4 F 0.19751(17) 0.79261(18) 0.73338(15) 0.0855(5) Uani 1 1 d . . . N1 N 0.48224(17) 0.59327(16) 0.79191(14) 0.0414(4) Uani 1 1 d . . . N2 N 0.23767(19) 0.54018(18) 0.64967(16) 0.0487(4) Uani 1 1 d . . . C1 C 0.6144(2) 0.6721(2) 0.89144(18) 0.0418(4) Uani 1 1 d . . . C2 C 0.6503(2) 0.8034(2) 0.9888(2) 0.0536(5) Uani 1 1 d . . . H2 H 0.5780 0.8569 0.9971 0.064 Uiso 1 1 calc R . . C3 C 0.7937(2) 0.8520(2) 1.0718(2) 0.0601(5) Uani 1 1 d . . . H3 H 0.8186 0.9399 1.1368 0.072 Uiso 1 1 calc R . . C4 C 0.9030(2) 0.7743(3) 1.0619(2) 0.0619(6) Uani 1 1 d . . . H4 H 1.0004 0.8110 1.1191 0.074 Uiso 1 1 calc R . . C5 C 0.8687(2) 0.6443(2) 0.9688(2) 0.0558(5) Uani 1 1 d . . . H5 H 0.9418 0.5914 0.9631 0.067 Uiso 1 1 calc R . . C6 C 0.7231(2) 0.5907(2) 0.88183(19) 0.0440(4) Uani 1 1 d . . . C7 C 0.6566(2) 0.4595(2) 0.77724(19) 0.0465(4) Uani 1 1 d . . . C8 C 0.5102(2) 0.4609(2) 0.72539(17) 0.0421(4) Uani 1 1 d . . . C9 C 0.3846(2) 0.3585(2) 0.62285(18) 0.0443(4) Uani 1 1 d . . . C10 C 0.3877(3) 0.2171(2) 0.5577(2) 0.0553(5) Uani 1 1 d . . . H10 H 0.4742 0.1838 0.5786 0.066 Uiso 1 1 calc R . . C11 C 0.2612(3) 0.1293(2) 0.4628(2) 0.0595(6) Uani 1 1 d . . . C12 C 0.1299(3) 0.1713(3) 0.4262(2) 0.0622(6) Uani 1 1 d . . . H12 H 0.0472 0.1086 0.3596 0.075 Uiso 1 1 calc R . . C13 C 0.1247(3) 0.3083(2) 0.4907(2) 0.0575(5) Uani 1 1 d . . . H13 H 0.0369 0.3395 0.4686 0.069 Uiso 1 1 calc R . . C14 C 0.2501(2) 0.4014(2) 0.58919(19) 0.0474(4) Uani 1 1 d . . . C15 C 0.3482(2) 0.6259(2) 0.74337(18) 0.0431(4) Uani 1 1 d . . . C16 C 0.3243(2) 0.7751(2) 0.7995(2) 0.0545(5) Uani 1 1 d . . . C17 C 0.7416(3) 0.3489(3) 0.7341(2) 0.0629(6) Uani 1 1 d . . . H17A H 0.6821 0.2434 0.7691 0.094 Uiso 1 1 calc R . . H17B H 0.8525 0.3901 0.7754 0.094 Uiso 1 1 calc R . . H17C H 0.7447 0.3424 0.6301 0.094 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 F1 0.0963(10) 0.0591(8) 0.1016(10) -0.0302(7) 0.0070(8) 0.0240(7) F2 0.0848(9) 0.0453(7) 0.0864(9) 0.0044(6) 0.0064(7) 0.0258(6) F3 0.0670(8) 0.0806(8) 0.0607(7) -0.0142(6) 0.0058(6) 0.0368(6) F4 0.0916(10) 0.0920(10) 0.0981(10) -0.0285(8) -0.0371(8) 0.0681(8) N1 0.0437(8) 0.0406(8) 0.0427(8) 0.0005(6) 0.0022(6) 0.0193(6) N2 0.0510(9) 0.0484(9) 0.0497(9) -0.0010(7) -0.0039(7) 0.0227(7) C1 0.0410(9) 0.0419(9) 0.0421(9) 0.0055(7) 0.0028(7) 0.0152(7) C2 0.0510(11) 0.0506(11) 0.0620(12) -0.0055(9) -0.0014(9) 0.0231(9) C3 0.0590(12) 0.0527(11) 0.0650(13) -0.0096(9) -0.0102(10) 0.0188(10) C4 0.0489(11) 0.0591(12) 0.0715(13) -0.0005(10) -0.0136(10) 0.0148(10) C5 0.0504(11) 0.0548(12) 0.0668(13) 0.0089(10) -0.0014(9) 0.0250(9) C6 0.0447(10) 0.0434(10) 0.0464(9) 0.0088(8) 0.0042(7) 0.0190(8) C7 0.0520(10) 0.0445(10) 0.0489(10) 0.0072(8) 0.0058(8) 0.0244(8) C8 0.0503(10) 0.0387(9) 0.0413(9) 0.0050(7) 0.0065(8) 0.0209(8) C9 0.0531(10) 0.0404(9) 0.0390(9) 0.0047(7) 0.0071(8) 0.0167(8) C10 0.0629(13) 0.0479(11) 0.0560(11) 0.0008(9) 0.0102(10) 0.0217(10) C11 0.0714(14) 0.0426(10) 0.0570(12) -0.0077(9) 0.0131(10) 0.0132(10) C12 0.0637(13) 0.0532(12) 0.0554(12) -0.0059(9) -0.0011(10) 0.0071(10) C13 0.0564(12) 0.0547(12) 0.0562(12) -0.0011(9) -0.0037(9) 0.0158(9) C14 0.0521(11) 0.0455(10) 0.0428(10) 0.0030(8) 0.0026(8) 0.0163(8) C15 0.0444(10) 0.0459(10) 0.0425(9) 0.0035(8) 0.0025(8) 0.0209(8) C16 0.0534(12) 0.0568(12) 0.0600(12) -0.0057(9) -0.0075(9) 0.0297(10) C17 0.0712(14) 0.0628(13) 0.0688(13) -0.0014(10) -0.0001(11) 0.0419(11) _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 F1 C11 1.355(2) . ? F2 C16 1.334(2) . ? F3 C16 1.331(2) . ? F4 C16 1.313(2) . ? N1 C15 1.377(2) . ? N1 C1 1.402(2) . ? N1 C8 1.426(2) . ? N2 C15 1.275(2) . ? N2 C14 1.393(2) . ? C1 C2 1.392(2) . ? C1 C6 1.403(2) . ? C2 C3 1.364(3) . ? C2 H2 0.9300 . ? C3 C4 1.384(3) . ? C3 H3 0.9300 . ? C4 C5 1.361(3) . ? C4 H4 0.9300 . ? C5 C6 1.398(2) . ? C5 H5 0.9300 . ? C6 C7 1.429(3) . ? C7 C8 1.358(2) . ? C7 C17 1.498(3) . ? C8 C9 1.441(2) . ? C9 C10 1.397(3) . ? C9 C14 1.398(3) . ? C10 C11 1.363(3) . ? C10 H10 0.9300 . ? C11 C12 1.374(3) . ? C12 C13 1.367(3) . ? C12 H12 0.9300 . ? C13 C14 1.391(3) . ? C13 H13 0.9300 . ? C15 C16 1.510(2) . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C15 N1 C1 133.43(14) . . ? C15 N1 C8 118.57(14) . . ? C1 N1 C8 107.80(14) . . ? C15 N2 C14 118.85(16) . . ? C2 C1 N1 133.24(16) . . ? C2 C1 C6 120.10(17) . . ? N1 C1 C6 106.66(15) . . ? C3 C2 C1 118.64(17) . . ? C3 C2 H2 120.7 . . ? C1 C2 H2 120.7 . . ? C2 C3 C4 121.83(19) . . ? C2 C3 H3 119.1 . . ? C4 C3 H3 119.1 . . ? C5 C4 C3 120.30(19) . . ? C5 C4 H4 119.9 . . ? C3 C4 H4 119.9 . . ? C4 C5 C6 119.62(19) . . ? C4 C5 H5 120.2 . . ? C6 C5 H5 120.2 . . ? C5 C6 C1 119.50(17) . . ? C5 C6 C7 131.37(17) . . ? C1 C6 C7 109.13(16) . . ? C8 C7 C6 106.93(15) . . ? C8 C7 C17 128.75(18) . . ? C6 C7 C17 124.29(17) . . ? C7 C8 N1 109.44(15) . . ? C7 C8 C9 133.49(16) . . ? N1 C8 C9 117.07(15) . . ? C10 C9 C14 118.23(17) . . ? C10 C9 C8 123.79(18) . . ? C14 C9 C8 117.97(16) . . ? C11 C10 C9 118.59(19) . . ? C11 C10 H10 120.7 . . ? C9 C10 H10 120.7 . . ? F1 C11 C10 118.0(2) . . ? F1 C11 C12 117.99(19) . . ? C10 C11 C12 123.99(19) . . ? C13 C12 C11 117.87(19) . . ? C13 C12 H12 121.1 . . ? C11 C12 H12 121.1 . . ? C12 C13 C14 120.3(2) . . ? C12 C13 H13 119.9 . . ? C14 C13 H13 119.9 . . ? C13 C14 N2 117.22(17) . . ? C13 C14 C9 121.01(17) . . ? N2 C14 C9 121.75(16) . . ? N2 C15 N1 125.41(16) . . ? N2 C15 C16 114.36(15) . . ? N1 C15 C16 120.22(15) . . ? F4 C16 F3 106.82(16) . . ? F4 C16 F2 106.92(17) . . ? F3 C16 F2 106.70(15) . . ? F4 C16 C15 111.66(15) . . ? F3 C16 C15 112.50(16) . . ? F2 C16 C15 111.89(15) . . ? C7 C17 H17A 109.5 . . ? C7 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C7 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C15 N1 C1 C2 7.7(3) . . . . ? C8 N1 C1 C2 -177.76(19) . . . . ? C15 N1 C1 C6 -172.93(16) . . . . ? C8 N1 C1 C6 1.63(18) . . . . ? N1 C1 C2 C3 -179.55(18) . . . . ? C6 C1 C2 C3 1.1(3) . . . . ? C1 C2 C3 C4 -0.2(3) . . . . ? C2 C3 C4 C5 -0.7(3) . . . . ? C3 C4 C5 C6 0.7(3) . . . . ? C4 C5 C6 C1 0.2(3) . . . . ? C4 C5 C6 C7 -179.58(18) . . . . ? C2 C1 C6 C5 -1.1(3) . . . . ? N1 C1 C6 C5 179.39(15) . . . . ? C2 C1 C6 C7 178.68(16) . . . . ? N1 C1 C6 C7 -0.80(19) . . . . ? C5 C6 C7 C8 179.40(18) . . . . ? C1 C6 C7 C8 -0.38(19) . . . . ? C5 C6 C7 C17 -2.5(3) . . . . ? C1 C6 C7 C17 177.74(17) . . . . ? C6 C7 C8 N1 1.41(19) . . . . ? C17 C7 C8 N1 -176.60(17) . . . . ? C6 C7 C8 C9 -177.85(18) . . . . ? C17 C7 C8 C9 4.1(3) . . . . ? C15 N1 C8 C7 173.57(14) . . . . ? C1 N1 C8 C7 -1.94(18) . . . . ? C15 N1 C8 C9 -7.0(2) . . . . ? C1 N1 C8 C9 177.46(14) . . . . ? C7 C8 C9 C10 4.5(3) . . . . ? N1 C8 C9 C10 -174.69(15) . . . . ? C7 C8 C9 C14 -176.91(17) . . . . ? N1 C8 C9 C14 3.9(2) . . . . ? C14 C9 C10 C11 1.0(3) . . . . ? C8 C9 C10 C11 179.58(17) . . . . ? C9 C10 C11 F1 -178.66(16) . . . . ? C9 C10 C11 C12 0.3(3) . . . . ? F1 C11 C12 C13 177.89(17) . . . . ? C10 C11 C12 C13 -1.1(3) . . . . ? C11 C12 C13 C14 0.5(3) . . . . ? C12 C13 C14 N2 179.39(17) . . . . ? C12 C13 C14 C9 0.9(3) . . . . ? C15 N2 C14 C13 178.10(17) . . . . ? C15 N2 C14 C9 -3.4(3) . . . . ? C10 C9 C14 C13 -1.6(3) . . . . ? C8 C9 C14 C13 179.74(16) . . . . ? C10 C9 C14 N2 179.93(15) . . . . ? C8 C9 C14 N2 1.3(3) . . . . ? C14 N2 C15 N1 -0.1(3) . . . . ? C14 N2 C15 C16 178.86(15) . . . . ? C1 N1 C15 N2 179.50(17) . . . . ? C8 N1 C15 N2 5.4(3) . . . . ? C1 N1 C15 C16 0.6(3) . . . . ? C8 N1 C15 C16 -173.47(14) . . . . ? N2 C15 C16 F4 -3.8(2) . . . . ? N1 C15 C16 F4 175.23(16) . . . . ? N2 C15 C16 F3 116.34(17) . . . . ? N1 C15 C16 F3 -64.7(2) . . . . ? N2 C15 C16 F2 -123.55(18) . . . . ? N1 C15 C16 F2 55.4(2) . . . . ? _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 0.220 _refine_diff_density_min -0.249 _refine_diff_density_rms 0.057 data_cd201336 _database_code_depnum_ccdc_archive 'CCDC 784284' #TrackingRef 'cd201336.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H13 F3 N2' _chemical_formula_weight 362.34 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 10.308(2) _cell_length_b 7.6365(16) _cell_length_c 42.549(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3349.4(12) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1968 _cell_measurement_theta_min 5.503 _cell_measurement_theta_max 41.115 _exptl_crystal_description prismatic _exptl_crystal_colour yellow _exptl_crystal_size_max 0.269 _exptl_crystal_size_mid 0.215 _exptl_crystal_size_min 0.065 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.437 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1488 _exptl_absorpt_coefficient_mu 0.109 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.54073 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details sadabs _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 16151 _diffrn_reflns_av_R_equivalents 0.1001 _diffrn_reflns_av_sigmaI/netI 0.0836 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -51 _diffrn_reflns_limit_l_max 49 _diffrn_reflns_theta_min 1.91 _diffrn_reflns_theta_max 25.50 _reflns_number_total 3124 _reflns_number_gt 1611 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.0807P)^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 0.0018(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3124 _refine_ls_number_parameters 245 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1215 _refine_ls_R_factor_gt 0.0684 _refine_ls_wR_factor_ref 0.1698 _refine_ls_wR_factor_gt 0.1563 _refine_ls_goodness_of_fit_ref 0.925 _refine_ls_restrained_S_all 0.925 _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 F1 F 0.48178(18) -0.0660(3) 0.17918(5) 0.0648(6) Uani 1 1 d . . . F2 F 0.6560(2) 0.0733(4) 0.18641(5) 0.0873(9) Uani 1 1 d . . . F3 F 0.6581(3) -0.1619(4) 0.16075(6) 0.1053(10) Uani 1 1 d . . . N1 N 0.6638(2) 0.0614(4) 0.11562(6) 0.0462(8) Uani 1 1 d . . . N2 N 0.4537(2) 0.1722(3) 0.12923(6) 0.0403(7) Uani 1 1 d . . . C1 C 0.5722(3) 0.0801(4) 0.13486(7) 0.0405(8) Uani 1 1 d . . . C2 C 0.5913(3) -0.0180(5) 0.16505(8) 0.0504(9) Uani 1 1 d . . . C3 C 0.6699(3) 0.1288(5) 0.08495(8) 0.0449(9) Uani 1 1 d . . . C4 C 0.7943(3) 0.1755(6) 0.07483(9) 0.0611(11) Uani 1 1 d . . . H4 H 0.8631 0.1692 0.0889 0.073 Uiso 1 1 calc R . . C5 C 0.8168(4) 0.2297(6) 0.04491(11) 0.0763(13) Uani 1 1 d . . . H5 H 0.9003 0.2600 0.0387 0.092 Uiso 1 1 calc R . . C6 C 0.7161(5) 0.2397(6) 0.02403(10) 0.0737(13) Uani 1 1 d . . . H6 H 0.7303 0.2791 0.0036 0.088 Uiso 1 1 calc R . . C7 C 0.5930(4) 0.1908(5) 0.03349(8) 0.0616(11) Uani 1 1 d . . . H7 H 0.5255 0.1956 0.0190 0.074 Uiso 1 1 calc R . . C8 C 0.5671(3) 0.1349(4) 0.06370(7) 0.0470(9) Uani 1 1 d . . . C9 C 0.4325(3) 0.0836(4) 0.07273(8) 0.0452(9) Uani 1 1 d . . . C10 C 0.3435(3) 0.0231(5) 0.05080(8) 0.0563(10) Uani 1 1 d . . . H10 H 0.3717 -0.0070 0.0308 0.068 Uiso 1 1 calc R . . C11 C 0.2126(4) 0.0067(5) 0.05834(9) 0.0643(11) Uani 1 1 d . . . H11 H 0.1554 -0.0360 0.0433 0.077 Uiso 1 1 calc R . . C12 C 0.1662(3) 0.0514(5) 0.08721(10) 0.0594(10) Uani 1 1 d . . . H12 H 0.0779 0.0444 0.0915 0.071 Uiso 1 1 calc R . . C13 C 0.2528(3) 0.1079(5) 0.11015(8) 0.0476(9) Uani 1 1 d . . . C14 C 0.3845(3) 0.1138(4) 0.10244(7) 0.0398(8) Uani 1 1 d . . . C15 C 0.3598(3) 0.2126(5) 0.15297(7) 0.0428(9) Uani 1 1 d . . . C16 C 0.2417(3) 0.1735(5) 0.14127(8) 0.0498(9) Uani 1 1 d . . . H16 H 0.1639 0.1875 0.1521 0.060 Uiso 1 1 calc R . . C17 C 0.3942(3) 0.2992(4) 0.18186(7) 0.0430(8) Uani 1 1 d . . . C18 C 0.3181(3) 0.2797(5) 0.20854(8) 0.0549(10) Uani 1 1 d . . . H18 H 0.2464 0.2058 0.2079 0.066 Uiso 1 1 calc R . . C19 C 0.3467(4) 0.3674(6) 0.23566(9) 0.0621(11) Uani 1 1 d . . . H19 H 0.2941 0.3529 0.2532 0.075 Uiso 1 1 calc R . . C20 C 0.4520(4) 0.4765(6) 0.23725(9) 0.0667(11) Uani 1 1 d . . . H20 H 0.4707 0.5364 0.2557 0.080 Uiso 1 1 calc R . . C21 C 0.5297(3) 0.4964(6) 0.21122(9) 0.0618(11) Uani 1 1 d . . . H21 H 0.6020 0.5690 0.2123 0.074 Uiso 1 1 calc R . . C22 C 0.5018(3) 0.4109(5) 0.18395(8) 0.0517(10) Uani 1 1 d . . . H22 H 0.5549 0.4268 0.1665 0.062 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 F1 0.0478(12) 0.0708(16) 0.0758(14) 0.0235(11) 0.0015(10) -0.0029(10) F2 0.0681(15) 0.124(2) 0.0696(15) 0.0226(14) -0.0297(11) -0.0222(14) F3 0.116(2) 0.103(2) 0.0967(19) 0.0346(15) 0.0278(14) 0.0691(18) N1 0.0309(15) 0.057(2) 0.0503(18) -0.0042(14) 0.0003(13) 0.0039(13) N2 0.0293(14) 0.0485(18) 0.0432(16) 0.0032(13) 0.0009(12) 0.0037(12) C1 0.0275(17) 0.045(2) 0.049(2) 0.0005(16) -0.0050(15) 0.0035(14) C2 0.037(2) 0.056(3) 0.059(2) 0.004(2) 0.0017(18) 0.0061(18) C3 0.0371(19) 0.049(2) 0.049(2) -0.0047(17) 0.0080(16) -0.0012(16) C4 0.047(2) 0.070(3) 0.066(3) -0.011(2) 0.0114(19) -0.0064(19) C5 0.063(3) 0.090(4) 0.075(3) -0.012(3) 0.026(2) -0.020(2) C6 0.096(4) 0.065(3) 0.060(3) 0.001(2) 0.031(3) -0.017(2) C7 0.073(3) 0.063(3) 0.048(2) 0.000(2) 0.002(2) 0.003(2) C8 0.049(2) 0.046(2) 0.046(2) -0.0018(17) 0.0060(17) 0.0027(17) C9 0.045(2) 0.043(2) 0.047(2) 0.0012(16) -0.0100(17) 0.0014(16) C10 0.059(2) 0.052(3) 0.058(2) -0.0001(19) -0.0125(18) 0.0045(19) C11 0.062(3) 0.054(3) 0.077(3) 0.000(2) -0.030(2) -0.005(2) C12 0.0338(19) 0.054(3) 0.090(3) 0.005(2) -0.015(2) -0.0056(17) C13 0.0337(18) 0.042(2) 0.067(2) 0.0085(18) -0.0042(17) -0.0016(15) C14 0.0336(17) 0.039(2) 0.047(2) 0.0060(16) -0.0074(15) 0.0042(14) C15 0.037(2) 0.045(2) 0.046(2) 0.0092(17) 0.0078(15) 0.0069(15) C16 0.0274(18) 0.055(2) 0.067(2) 0.0052(19) 0.0056(16) 0.0033(16) C17 0.0378(19) 0.044(2) 0.047(2) 0.0058(17) 0.0065(15) 0.0114(16) C18 0.050(2) 0.056(3) 0.059(2) 0.007(2) 0.0123(18) 0.0095(18) C19 0.063(3) 0.068(3) 0.055(3) 0.007(2) 0.0179(19) 0.012(2) C20 0.071(3) 0.076(3) 0.054(2) -0.007(2) -0.001(2) 0.015(2) C21 0.052(2) 0.077(3) 0.057(2) -0.006(2) -0.0002(19) -0.001(2) C22 0.040(2) 0.065(3) 0.051(2) -0.0007(19) 0.0060(16) 0.0045(18) _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 F1 C2 1.330(4) . ? F2 C2 1.325(4) . ? F3 C2 1.310(4) . ? N1 C1 1.258(4) . ? N1 C3 1.404(4) . ? N2 C14 1.417(4) . ? N2 C1 1.430(4) . ? N2 C15 1.433(4) . ? C1 C2 1.500(5) . ? C3 C8 1.394(4) . ? C3 C4 1.399(4) . ? C4 C5 1.359(5) . ? C4 H4 0.9300 . ? C5 C6 1.369(6) . ? C5 H5 0.9300 . ? C6 C7 1.383(5) . ? C6 H6 0.9300 . ? C7 C8 1.380(4) . ? C7 H7 0.9300 . ? C8 C9 1.492(4) . ? C9 C14 1.377(4) . ? C9 C10 1.388(4) . ? C10 C11 1.393(5) . ? C10 H10 0.9300 . ? C11 C12 1.362(5) . ? C11 H11 0.9300 . ? C12 C13 1.392(5) . ? C12 H12 0.9300 . ? C13 C14 1.397(4) . ? C13 C16 1.420(5) . ? C15 C16 1.348(4) . ? C15 C17 1.440(4) . ? C16 H16 0.9300 . ? C17 C18 1.388(4) . ? C17 C22 1.402(5) . ? C18 C19 1.366(5) . ? C18 H18 0.9300 . ? C19 C20 1.370(5) . ? C19 H19 0.9300 . ? C20 C21 1.375(5) . ? C20 H20 0.9300 . ? C21 C22 1.362(5) . ? C21 H21 0.9300 . ? C22 H22 0.9300 . ? 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 C1 N1 C3 126.7(3) . . ? C14 N2 C1 114.2(2) . . ? C14 N2 C15 107.1(2) . . ? C1 N2 C15 124.4(2) . . ? N1 C1 N2 126.0(3) . . ? N1 C1 C2 113.7(3) . . ? N2 C1 C2 120.1(3) . . ? F3 C2 F2 105.8(3) . . ? F3 C2 F1 106.1(3) . . ? F2 C2 F1 105.2(3) . . ? F3 C2 C1 111.6(3) . . ? F2 C2 C1 113.0(3) . . ? F1 C2 C1 114.4(3) . . ? C8 C3 C4 119.2(3) . . ? C8 C3 N1 125.5(3) . . ? C4 C3 N1 114.9(3) . . ? C5 C4 C3 121.5(4) . . ? C5 C4 H4 119.2 . . ? C3 C4 H4 119.2 . . ? C4 C5 C6 119.7(4) . . ? C4 C5 H5 120.2 . . ? C6 C5 H5 120.2 . . ? C5 C6 C7 119.5(4) . . ? C5 C6 H6 120.3 . . ? C7 C6 H6 120.3 . . ? C8 C7 C6 122.2(4) . . ? C8 C7 H7 118.9 . . ? C6 C7 H7 118.9 . . ? C7 C8 C3 117.9(3) . . ? C7 C8 C9 120.1(3) . . ? C3 C8 C9 122.1(3) . . ? C14 C9 C10 115.8(3) . . ? C14 C9 C8 121.8(3) . . ? C10 C9 C8 121.9(3) . . ? C9 C10 C11 121.0(3) . . ? C9 C10 H10 119.5 . . ? C11 C10 H10 119.5 . . ? C12 C11 C10 121.7(3) . . ? C12 C11 H11 119.1 . . ? C10 C11 H11 119.1 . . ? C11 C12 C13 119.0(3) . . ? C11 C12 H12 120.5 . . ? C13 C12 H12 120.5 . . ? C12 C13 C14 118.0(3) . . ? C12 C13 C16 135.3(3) . . ? C14 C13 C16 106.6(3) . . ? C9 C14 C13 124.0(3) . . ? C9 C14 N2 127.6(3) . . ? C13 C14 N2 108.1(3) . . ? C16 C15 N2 107.6(3) . . ? C16 C15 C17 129.7(3) . . ? N2 C15 C17 122.3(3) . . ? C15 C16 C13 110.4(3) . . ? C15 C16 H16 124.8 . . ? C13 C16 H16 124.8 . . ? C18 C17 C22 117.4(3) . . ? C18 C17 C15 120.6(3) . . ? C22 C17 C15 121.9(3) . . ? C19 C18 C17 121.1(4) . . ? C19 C18 H18 119.5 . . ? C17 C18 H18 119.5 . . ? C18 C19 C20 120.7(3) . . ? C18 C19 H19 119.6 . . ? C20 C19 H19 119.6 . . ? C19 C20 C21 119.3(4) . . ? C19 C20 H20 120.4 . . ? C21 C20 H20 120.4 . . ? C22 C21 C20 120.7(4) . . ? C22 C21 H21 119.6 . . ? C20 C21 H21 119.6 . . ? C21 C22 C17 120.8(3) . . ? C21 C22 H22 119.6 . . ? C17 C22 H22 119.6 . . ? 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 C3 N1 C1 N2 1.1(5) . . . . ? C3 N1 C1 C2 176.2(3) . . . . ? C14 N2 C1 N1 55.1(4) . . . . ? C15 N2 C1 N1 -170.6(3) . . . . ? C14 N2 C1 C2 -119.8(3) . . . . ? C15 N2 C1 C2 14.6(5) . . . . ? N1 C1 C2 F3 -31.1(4) . . . . ? N2 C1 C2 F3 144.4(3) . . . . ? N1 C1 C2 F2 88.0(4) . . . . ? N2 C1 C2 F2 -96.5(3) . . . . ? N1 C1 C2 F1 -151.6(3) . . . . ? N2 C1 C2 F1 23.9(5) . . . . ? C1 N1 C3 C8 -40.1(5) . . . . ? C1 N1 C3 C4 146.7(4) . . . . ? C8 C3 C4 C5 1.2(6) . . . . ? N1 C3 C4 C5 174.8(4) . . . . ? C3 C4 C5 C6 0.1(6) . . . . ? C4 C5 C6 C7 -1.4(7) . . . . ? C5 C6 C7 C8 1.3(6) . . . . ? C6 C7 C8 C3 0.0(6) . . . . ? C6 C7 C8 C9 180.0(3) . . . . ? C4 C3 C8 C7 -1.2(5) . . . . ? N1 C3 C8 C7 -174.1(3) . . . . ? C4 C3 C8 C9 178.8(3) . . . . ? N1 C3 C8 C9 5.9(5) . . . . ? C7 C8 C9 C14 -145.9(3) . . . . ? C3 C8 C9 C14 34.1(5) . . . . ? C7 C8 C9 C10 26.0(5) . . . . ? C3 C8 C9 C10 -154.1(3) . . . . ? C14 C9 C10 C11 4.3(5) . . . . ? C8 C9 C10 C11 -168.0(3) . . . . ? C9 C10 C11 C12 1.0(6) . . . . ? C10 C11 C12 C13 -2.8(6) . . . . ? C11 C12 C13 C14 -0.8(5) . . . . ? C11 C12 C13 C16 175.5(4) . . . . ? C10 C9 C14 C13 -8.2(5) . . . . ? C8 C9 C14 C13 164.1(3) . . . . ? C10 C9 C14 N2 178.8(3) . . . . ? C8 C9 C14 N2 -8.9(5) . . . . ? C12 C13 C14 C9 6.6(5) . . . . ? C16 C13 C14 C9 -170.7(3) . . . . ? C12 C13 C14 N2 -179.2(3) . . . . ? C16 C13 C14 N2 3.5(4) . . . . ? C1 N2 C14 C9 -47.8(4) . . . . ? C15 N2 C14 C9 170.3(3) . . . . ? C1 N2 C14 C13 138.3(3) . . . . ? C15 N2 C14 C13 -3.6(3) . . . . ? C14 N2 C15 C16 2.3(4) . . . . ? C1 N2 C15 C16 -134.7(3) . . . . ? C14 N2 C15 C17 -171.0(3) . . . . ? C1 N2 C15 C17 52.0(4) . . . . ? N2 C15 C16 C13 -0.1(4) . . . . ? C17 C15 C16 C13 172.5(3) . . . . ? C12 C13 C16 C15 -178.7(4) . . . . ? C14 C13 C16 C15 -2.1(4) . . . . ? C16 C15 C17 C18 32.6(5) . . . . ? N2 C15 C17 C18 -155.8(3) . . . . ? C16 C15 C17 C22 -145.0(4) . . . . ? N2 C15 C17 C22 26.7(5) . . . . ? C22 C17 C18 C19 0.6(5) . . . . ? C15 C17 C18 C19 -177.1(3) . . . . ? C17 C18 C19 C20 -0.4(6) . . . . ? C18 C19 C20 C21 -0.4(6) . . . . ? C19 C20 C21 C22 0.9(6) . . . . ? C20 C21 C22 C17 -0.7(6) . . . . ? C18 C17 C22 C21 -0.1(5) . . . . ? C15 C17 C22 C21 177.6(3) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.244 _refine_diff_density_min -0.234 _refine_diff_density_rms 0.059