data_a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C17 H14 F6 N2' _chemical_formula_sum 'C17 H14 F6 N2' _chemical_formula_weight 360.30 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 Monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' 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 12.7506(10) _cell_length_b 9.9723(8) _cell_length_c 13.5743(11) _cell_angle_alpha 90.00 _cell_angle_beta 116.3980(10) _cell_angle_gamma 90.00 _cell_volume 1546.0(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 309 _cell_measurement_theta_min 3 _cell_measurement_theta_max 28 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.29 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.548 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 736 _exptl_absorpt_coefficient_mu 0.143 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.960 _exptl_absorpt_correction_T_max 0.965 _exptl_absorpt_process_details 'SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'Bruker APEX II CCD area detector'' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 16679 _diffrn_reflns_av_R_equivalents 0.0595 _diffrn_reflns_av_sigmaI/netI 0.0351 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.82 _diffrn_reflns_theta_max 28.99 _reflns_number_total 4106 _reflns_number_gt 3329 _reflns_threshold_expression 'I>2\s(I)' _computing_data_collection 'Bruker APEX II' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _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^)+(0.0919P)^2^+0.2477P] 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 4106 _refine_ls_number_parameters 227 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0564 _refine_ls_R_factor_gt 0.0482 _refine_ls_wR_factor_ref 0.1432 _refine_ls_wR_factor_gt 0.1339 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.035 _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 0.79340(7) 0.74344(10) 0.37698(7) 0.0339(2) Uani 1 1 d . . . F2 F 0.74697(7) 0.72971(9) 0.20456(7) 0.0325(2) Uani 1 1 d . . . F3 F 0.74910(8) 0.92131(9) 0.27803(8) 0.0366(2) Uani 1 1 d . . . F4 F 0.53706(9) 0.90089(9) 0.08872(7) 0.0378(2) Uani 1 1 d . . . F5 F 0.51817(7) 0.68750(9) 0.07013(6) 0.0311(2) Uani 1 1 d . . . F6 F 0.40034(7) 0.80033(9) 0.11287(7) 0.0322(2) Uani 1 1 d . . . N1 N 0.58173(9) 0.68557(10) 0.55304(8) 0.0206(2) Uani 1 1 d . . . N7 N 0.56719(9) 0.86354(10) 0.32520(9) 0.0217(2) Uani 1 1 d . . . C2 C 0.64258(10) 0.57961(12) 0.61390(10) 0.0200(2) Uani 1 1 d . . . C3 C 0.68673(11) 0.48029(12) 0.56982(10) 0.0222(3) Uani 1 1 d . . . H3A H 0.7280 0.4060 0.6137 0.027 Uiso 1 1 calc R . . C4A C 0.60723(10) 0.59914(12) 0.39954(10) 0.0196(2) Uani 1 1 d . . . C4 C 0.67005(11) 0.49056(12) 0.46168(10) 0.0216(3) Uani 1 1 d . . . H4A H 0.7009 0.4248 0.4311 0.026 Uiso 1 1 calc R . . C5 C 0.57680(11) 0.62227(12) 0.28056(10) 0.0203(2) Uani 1 1 d . . . H5A H 0.4946 0.5949 0.2349 0.024 Uiso 1 1 calc R . . H5B H 0.6274 0.5651 0.2599 0.024 Uiso 1 1 calc R . . C6 C 0.59207(10) 0.77150(12) 0.25524(10) 0.0205(2) Uani 1 1 d . . . C8A C 0.56442(10) 0.69149(12) 0.44883(10) 0.0198(2) Uani 1 1 d . . . C8 C 0.49868(11) 0.80807(12) 0.37881(10) 0.0221(3) Uani 1 1 d . . . H8A H 0.4210 0.7783 0.3225 0.027 Uiso 1 1 calc R . . H8B H 0.4867 0.8776 0.4249 0.027 Uiso 1 1 calc R . . C9 C 0.53061(13) 1.00114(13) 0.28674(11) 0.0285(3) Uani 1 1 d . . . H9A H 0.5803 1.0371 0.2549 0.043 Uiso 1 1 calc R . . H9B H 0.5383 1.0573 0.3489 0.043 Uiso 1 1 calc R . . H9C H 0.4488 1.0009 0.2308 0.043 Uiso 1 1 calc R . . C10 C 0.51181(12) 0.79064(14) 0.13037(11) 0.0267(3) Uani 1 1 d . . . C11 C 0.72099(12) 0.79194(14) 0.27864(11) 0.0253(3) Uani 1 1 d . . . C12 C 0.65842(11) 0.57680(12) 0.72926(10) 0.0213(3) Uani 1 1 d . . . C13 C 0.59707(12) 0.66854(14) 0.76208(11) 0.0267(3) Uani 1 1 d . . . H13A H 0.5472 0.7325 0.7108 0.032 Uiso 1 1 calc R . . C14 C 0.60800(14) 0.66756(15) 0.86856(12) 0.0312(3) Uani 1 1 d . . . H14A H 0.5657 0.7306 0.8894 0.037 Uiso 1 1 calc R . . C15 C 0.68081(13) 0.57442(14) 0.94485(11) 0.0302(3) Uani 1 1 d . . . H15A H 0.6887 0.5739 1.0178 0.036 Uiso 1 1 calc R . . C16 C 0.74151(12) 0.48265(14) 0.91319(11) 0.0278(3) Uani 1 1 d . . . H16A H 0.7908 0.4185 0.9647 0.033 Uiso 1 1 calc R . . C17 C 0.73115(11) 0.48331(14) 0.80655(10) 0.0244(3) Uani 1 1 d . . . H17A H 0.7736 0.4200 0.7861 0.029 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 0.0183(4) 0.0489(5) 0.0246(4) 0.0067(4) 0.0006(3) -0.0032(3) F2 0.0290(4) 0.0391(5) 0.0311(5) 0.0008(4) 0.0150(4) 0.0026(3) F3 0.0351(5) 0.0303(5) 0.0460(5) -0.0001(4) 0.0194(4) -0.0100(3) F4 0.0487(5) 0.0345(5) 0.0239(4) 0.0105(3) 0.0107(4) 0.0002(4) F5 0.0336(4) 0.0351(5) 0.0173(4) -0.0015(3) 0.0046(3) 0.0037(3) F6 0.0240(4) 0.0383(5) 0.0212(4) 0.0009(3) -0.0017(3) 0.0069(3) N1 0.0184(5) 0.0213(5) 0.0178(5) 0.0010(4) 0.0043(4) 0.0001(4) N7 0.0248(5) 0.0179(5) 0.0180(5) 0.0027(4) 0.0057(4) 0.0021(4) C2 0.0168(5) 0.0203(6) 0.0177(5) 0.0012(4) 0.0027(4) -0.0028(4) C3 0.0199(5) 0.0201(6) 0.0205(6) 0.0023(4) 0.0034(5) 0.0002(4) C4A 0.0165(5) 0.0199(6) 0.0179(5) 0.0006(4) 0.0037(4) -0.0014(4) C4 0.0212(6) 0.0190(5) 0.0210(6) 0.0000(4) 0.0063(5) 0.0011(4) C5 0.0194(5) 0.0197(5) 0.0169(5) 0.0001(4) 0.0036(4) -0.0002(4) C6 0.0187(5) 0.0219(6) 0.0152(5) 0.0015(4) 0.0024(4) -0.0001(4) C8A 0.0162(5) 0.0203(6) 0.0176(5) 0.0018(4) 0.0029(4) -0.0004(4) C8 0.0210(6) 0.0232(6) 0.0186(5) 0.0028(4) 0.0056(5) 0.0035(4) C9 0.0342(7) 0.0211(6) 0.0248(6) 0.0041(5) 0.0083(6) 0.0036(5) C10 0.0275(6) 0.0284(6) 0.0172(6) 0.0030(5) 0.0038(5) 0.0020(5) C11 0.0236(6) 0.0272(6) 0.0215(6) 0.0022(5) 0.0068(5) -0.0031(5) C12 0.0192(5) 0.0223(6) 0.0167(5) 0.0007(4) 0.0030(4) -0.0044(4) C13 0.0337(7) 0.0214(6) 0.0210(6) 0.0015(5) 0.0086(5) 0.0012(5) C14 0.0446(8) 0.0243(6) 0.0229(6) -0.0010(5) 0.0133(6) 0.0013(6) C15 0.0366(7) 0.0301(7) 0.0177(6) -0.0002(5) 0.0066(5) -0.0040(6) C16 0.0239(6) 0.0316(7) 0.0183(6) 0.0050(5) 0.0009(5) -0.0020(5) C17 0.0195(6) 0.0280(6) 0.0193(6) 0.0026(5) 0.0029(5) -0.0004(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag F1 C11 1.3314(15) . ? F2 C11 1.3425(16) . ? F3 C11 1.3400(16) . ? F4 C10 1.3394(16) . ? F5 C10 1.3386(16) . ? F6 C10 1.3363(17) . ? N1 C8A 1.3325(16) . ? N1 C2 1.3532(16) . ? N7 C6 1.4535(16) . ? N7 C9 1.4685(16) . ? N7 C8 1.4710(16) . ? C2 C3 1.3984(18) . ? C2 C12 1.4876(17) . ? C3 C4 1.3902(17) . ? C3 H3A 0.9500 . ? C4A C8A 1.3850(17) . ? C4A C4 1.3874(17) . ? C4A C5 1.5017(17) . ? C4 H4A 0.9500 . ? C5 C6 1.5589(17) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C11 1.5428(18) . ? C6 C10 1.5539(18) . ? C8A C8 1.4997(16) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C12 C13 1.3990(19) . ? C12 C17 1.4017(17) . ? C13 C14 1.3890(19) . ? C13 H13A 0.9500 . ? C14 C15 1.394(2) . ? C14 H14A 0.9500 . ? C15 C16 1.385(2) . ? C15 H15A 0.9500 . ? C16 C17 1.3938(18) . ? C16 H16A 0.9500 . ? C17 H17A 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C8A N1 C2 117.52(11) . . ? C6 N7 C9 119.01(10) . . ? C6 N7 C8 115.84(10) . . ? C9 N7 C8 111.26(10) . . ? N1 C2 C3 121.50(11) . . ? N1 C2 C12 115.47(11) . . ? C3 C2 C12 123.03(11) . . ? C4 C3 C2 119.86(11) . . ? C4 C3 H3A 120.1 . . ? C2 C3 H3A 120.1 . . ? C8A C4A C4 118.05(11) . . ? C8A C4A C5 116.65(10) . . ? C4 C4A C5 125.24(11) . . ? C4A C4 C3 118.39(11) . . ? C4A C4 H4A 120.8 . . ? C3 C4 H4A 120.8 . . ? C4A C5 C6 112.70(10) . . ? C4A C5 H5A 109.1 . . ? C6 C5 H5A 109.1 . . ? C4A C5 H5B 109.1 . . ? C6 C5 H5B 109.1 . . ? H5A C5 H5B 107.8 . . ? N7 C6 C11 107.71(10) . . ? N7 C6 C10 113.95(10) . . ? C11 C6 C10 109.45(11) . . ? N7 C6 C5 111.95(10) . . ? C11 C6 C5 107.87(10) . . ? C10 C6 C5 105.75(10) . . ? N1 C8A C4A 124.64(11) . . ? N1 C8A C8 119.29(11) . . ? C4A C8A C8 116.01(11) . . ? N7 C8 C8A 108.52(10) . . ? N7 C8 H8A 110.0 . . ? C8A C8 H8A 110.0 . . ? N7 C8 H8B 110.0 . . ? C8A C8 H8B 110.0 . . ? H8A C8 H8B 108.4 . . ? N7 C9 H9A 109.5 . . ? N7 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? N7 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? F6 C10 F5 107.18(11) . . ? F6 C10 F4 107.57(11) . . ? F5 C10 F4 106.36(11) . . ? F6 C10 C6 109.59(11) . . ? F5 C10 C6 112.50(11) . . ? F4 C10 C6 113.33(11) . . ? F1 C11 F3 106.72(11) . . ? F1 C11 F2 106.92(11) . . ? F3 C11 F2 106.54(11) . . ? F1 C11 C6 111.03(11) . . ? F3 C11 C6 112.92(11) . . ? F2 C11 C6 112.33(11) . . ? C13 C12 C17 118.31(12) . . ? C13 C12 C2 119.31(11) . . ? C17 C12 C2 122.38(12) . . ? C14 C13 C12 121.00(12) . . ? C14 C13 H13A 119.5 . . ? C12 C13 H13A 119.5 . . ? C13 C14 C15 120.22(14) . . ? C13 C14 H14A 119.9 . . ? C15 C14 H14A 119.9 . . ? C16 C15 C14 119.31(13) . . ? C16 C15 H15A 120.3 . . ? C14 C15 H15A 120.3 . . ? C15 C16 C17 120.75(12) . . ? C15 C16 H16A 119.6 . . ? C17 C16 H16A 119.6 . . ? C16 C17 C12 120.41(13) . . ? C16 C17 H17A 119.8 . . ? C12 C17 H17A 119.8 . . ? 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 C8A N1 C2 C3 0.52(17) . . . . ? C8A N1 C2 C12 -179.35(10) . . . . ? N1 C2 C3 C4 1.10(18) . . . . ? C12 C2 C3 C4 -179.04(11) . . . . ? C8A C4A C4 C3 -0.06(17) . . . . ? C5 C4A C4 C3 -177.19(11) . . . . ? C2 C3 C4 C4A -1.30(18) . . . . ? C8A C4A C5 C6 44.65(14) . . . . ? C4 C4A C5 C6 -138.18(12) . . . . ? C9 N7 C6 C11 86.09(13) . . . . ? C8 N7 C6 C11 -137.09(10) . . . . ? C9 N7 C6 C10 -35.53(16) . . . . ? C8 N7 C6 C10 101.29(12) . . . . ? C9 N7 C6 C5 -155.48(11) . . . . ? C8 N7 C6 C5 -18.67(14) . . . . ? C4A C5 C6 N7 -32.35(14) . . . . ? C4A C5 C6 C11 85.97(12) . . . . ? C4A C5 C6 C10 -157.00(11) . . . . ? C2 N1 C8A C4A -2.02(18) . . . . ? C2 N1 C8A C8 -179.26(11) . . . . ? C4 C4A C8A N1 1.80(18) . . . . ? C5 C4A C8A N1 179.19(11) . . . . ? C4 C4A C8A C8 179.12(11) . . . . ? C5 C4A C8A C8 -3.50(16) . . . . ? C6 N7 C8 C8A 59.22(13) . . . . ? C9 N7 C8 C8A -160.73(10) . . . . ? N1 C8A C8 N7 130.03(11) . . . . ? C4A C8A C8 N7 -47.44(14) . . . . ? N7 C6 C10 F6 -46.79(14) . . . . ? C11 C6 C10 F6 -167.44(11) . . . . ? C5 C6 C10 F6 76.60(13) . . . . ? N7 C6 C10 F5 -165.92(11) . . . . ? C11 C6 C10 F5 73.43(14) . . . . ? C5 C6 C10 F5 -42.53(14) . . . . ? N7 C6 C10 F4 73.37(15) . . . . ? C11 C6 C10 F4 -47.27(15) . . . . ? C5 C6 C10 F4 -163.23(11) . . . . ? N7 C6 C11 F1 71.69(13) . . . . ? C10 C6 C11 F1 -163.93(11) . . . . ? C5 C6 C11 F1 -49.32(14) . . . . ? N7 C6 C11 F3 -48.12(14) . . . . ? C10 C6 C11 F3 76.26(14) . . . . ? C5 C6 C11 F3 -169.14(10) . . . . ? N7 C6 C11 F2 -168.64(10) . . . . ? C10 C6 C11 F2 -44.26(14) . . . . ? C5 C6 C11 F2 70.35(13) . . . . ? N1 C2 C12 C13 9.36(17) . . . . ? C3 C2 C12 C13 -170.51(12) . . . . ? N1 C2 C12 C17 -171.99(11) . . . . ? C3 C2 C12 C17 8.14(19) . . . . ? C17 C12 C13 C14 0.2(2) . . . . ? C2 C12 C13 C14 178.89(12) . . . . ? C12 C13 C14 C15 0.0(2) . . . . ? C13 C14 C15 C16 -0.3(2) . . . . ? C14 C15 C16 C17 0.5(2) . . . . ? C15 C16 C17 C12 -0.3(2) . . . . ? C13 C12 C17 C16 -0.03(19) . . . . ? C2 C12 C17 C16 -178.69(11) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 28.99 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.516 _refine_diff_density_min -0.294 _refine_diff_density_rms 0.070 _publ_section_references ; Bruker, Programs APEX II, version 2.0-1; SAINT, version 7.23A; SADABS, version 2004/1; XPREP, version 2005/2; SHELXTL, version 6.1. Bruker AXS Inc., Madison, WI, USA, 2005. G.M. Sheldrick, Programs SHELXS97 (crystal structure solution) and SHELXL97 (crystal structure refinement), University of Gottingen, Germany, 1997. ; _publ_section_exptl_refinement ; The H(C) atom positions were calculated and refined in isotropic approximation in riding model with the Uiso(H) parameters equal to 1.2 Ueq(Ci), where U(Ci) and U(Cii) are respectively the equivalent thermal parameters of the atoms to which corresponding H atoms are bonded. ;