# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_cd213126 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H20 F5 N3 O3' _chemical_formula_weight 457.40 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 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 10.4352(16) _cell_length_b 9.1374(13) _cell_length_c 42.862(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.359(3) _cell_angle_gamma 90.00 _cell_volume 4086.8(11) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 4530 _cell_measurement_theta_min 4.756 _cell_measurement_theta_max 52.711 _exptl_crystal_description prismatic _exptl_crystal_colour colorless _exptl_crystal_size_max 0.257 _exptl_crystal_size_mid 0.211 _exptl_crystal_size_min 0.123 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.487 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1888 _exptl_absorpt_coefficient_mu 0.131 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.26426 _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 23870 _diffrn_reflns_av_R_equivalents 0.0872 _diffrn_reflns_av_sigmaI/netI 0.0709 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -50 _diffrn_reflns_limit_l_max 52 _diffrn_reflns_theta_min 1.90 _diffrn_reflns_theta_max 26.00 _reflns_number_total 8018 _reflns_number_gt 4983 _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^)+(0.0964P)^2^+0.1792P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 8018 _refine_ls_number_parameters 601 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.1029 _refine_ls_R_factor_gt 0.0638 _refine_ls_wR_factor_ref 0.1862 _refine_ls_wR_factor_gt 0.1644 _refine_ls_goodness_of_fit_ref 1.002 _refine_ls_restrained_S_all 1.001 _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 N1 N 0.6950(2) 0.1180(2) 0.15035(5) 0.0456(6) Uani 1 1 d D . . N2 N 0.9953(3) -0.0057(3) 0.27073(6) 0.0624(7) Uani 1 1 d D . . N3 N 1.2586(2) 0.1227(3) 0.38103(5) 0.0476(6) Uani 1 1 d D . . N4 N 0.2227(2) 0.6666(3) 0.14762(5) 0.0470(6) Uani 1 1 d D . . N5 N 0.5321(3) 0.5893(3) 0.26780(5) 0.0568(7) Uani 1 1 d D . . N6 N 0.7834(2) 0.6663(3) 0.37960(5) 0.0453(6) Uani 1 1 d D . . O1 O 0.6204(2) -0.0707(2) 0.12199(4) 0.0586(6) Uani 1 1 d . . . O2 O 0.9287(3) 0.2130(2) 0.25450(5) 0.0829(8) Uani 1 1 d . . . O3 O 1.2120(2) -0.0872(2) 0.35572(4) 0.0570(6) Uani 1 1 d . . . O4 O 0.1267(2) 0.4717(2) 0.12595(4) 0.0551(5) Uani 1 1 d . . . O5 O 0.5444(3) 0.7914(2) 0.23803(5) 0.0760(7) Uani 1 1 d . . . O6 O 0.7198(2) 0.4700(2) 0.35158(4) 0.0618(6) Uani 1 1 d . . . F1 F 0.65718(18) 0.0257(2) 0.06025(4) 0.0667(5) Uani 1 1 d . . . F2 F 0.56001(19) 0.2110(2) 0.01845(4) 0.0749(6) Uani 1 1 d . . . F3 F 0.43426(18) 0.4531(2) 0.03692(4) 0.0732(6) Uani 1 1 d . . . F4 F 0.41350(18) 0.5137(2) 0.09849(4) 0.0708(5) Uani 1 1 d . . . F5 F 0.50434(16) 0.32837(18) 0.14082(3) 0.0566(5) Uani 1 1 d . . . F6 F 0.16177(18) 0.56038(19) 0.06142(4) 0.0633(5) Uani 1 1 d . . . F7 F 0.05311(19) 0.7363(2) 0.01944(4) 0.0725(6) Uani 1 1 d . . . F8 F -0.07775(18) 0.9753(2) 0.03755(4) 0.0736(6) Uani 1 1 d . . . F9 F -0.09570(17) 1.0399(2) 0.09921(4) 0.0694(5) Uani 1 1 d . . . F10 F 0.00630(16) 0.86040(19) 0.14172(3) 0.0593(5) Uani 1 1 d . . . C1 C 0.5965(3) 0.1444(3) 0.07068(6) 0.0465(7) Uani 1 1 d . . . C2 C 0.5474(3) 0.2393(3) 0.04882(6) 0.0501(7) Uani 1 1 d . . . C3 C 0.4847(3) 0.3625(3) 0.05794(6) 0.0504(7) Uani 1 1 d . . . C4 C 0.4732(3) 0.3918(3) 0.08924(6) 0.0476(7) Uani 1 1 d . . . C5 C 0.5230(3) 0.2958(3) 0.11062(6) 0.0423(6) Uani 1 1 d . . . C6 C 0.5865(2) 0.1695(3) 0.10242(6) 0.0395(6) Uani 1 1 d . . . C7 C 0.6360(3) 0.0613(3) 0.12576(6) 0.0429(6) Uani 1 1 d . . . C8 C 0.7491(3) 0.0237(3) 0.17410(6) 0.0474(7) Uani 1 1 d . . . H8A H 0.8121 -0.0402 0.1647 0.057 Uiso 1 1 calc R . . H8B H 0.6818 -0.0372 0.1827 0.057 Uiso 1 1 calc R . . C9 C 0.8119(3) 0.1087(3) 0.20018(6) 0.0507(7) Uani 1 1 d . . . H9A H 0.7475 0.1644 0.2113 0.061 Uiso 1 1 calc R . . H9B H 0.8734 0.1771 0.1916 0.061 Uiso 1 1 calc R . . C10 C 0.8792(3) 0.0063(3) 0.22256(6) 0.0567(8) Uani 1 1 d . . . H10A H 0.8182 -0.0663 0.2297 0.068 Uiso 1 1 calc R . . H10B H 0.9463 -0.0449 0.2114 0.068 Uiso 1 1 calc R . . C11 C 0.9374(3) 0.0813(3) 0.25052(6) 0.0532(8) Uani 1 1 d . . . C12 C 1.0566(3) 0.0466(4) 0.29910(6) 0.0598(8) Uani 1 1 d . . . H12A H 1.0332 -0.0170 0.3163 0.072 Uiso 1 1 calc R . . H12B H 1.0248 0.1439 0.3038 0.072 Uiso 1 1 calc R . . C13 C 1.1986(3) 0.0520(4) 0.29679(6) 0.0582(8) Uani 1 1 d . . . H13A H 1.2221 0.1065 0.2783 0.070 Uiso 1 1 calc R . . H13B H 1.2314 -0.0468 0.2946 0.070 Uiso 1 1 calc R . . C14 C 1.2602(3) 0.1234(4) 0.32529(6) 0.0633(9) Uani 1 1 d . . . H14A H 1.3515 0.1329 0.3217 0.076 Uiso 1 1 calc R . . H14B H 1.2254 0.2212 0.3276 0.076 Uiso 1 1 calc R . . C15 C 1.2410(3) 0.0418(3) 0.35521(6) 0.0436(7) Uani 1 1 d . . . C16 C 1.2463(3) 0.0793(3) 0.41242(6) 0.0433(7) Uani 1 1 d . . . C17 C 1.3077(3) 0.1640(3) 0.43476(6) 0.0540(8) Uani 1 1 d . . . H17 H 1.3562 0.2445 0.4287 0.065 Uiso 1 1 calc R . . C18 C 1.2970(3) 0.1294(4) 0.46580(7) 0.0659(9) Uani 1 1 d . . . H18 H 1.3385 0.1867 0.4807 0.079 Uiso 1 1 calc R . . C19 C 1.2261(4) 0.0118(4) 0.47506(7) 0.0712(10) Uani 1 1 d . . . H19 H 1.2197 -0.0115 0.4961 0.085 Uiso 1 1 calc R . . C20 C 1.1641(3) -0.0722(4) 0.45293(7) 0.0633(9) Uani 1 1 d . . . H20 H 1.1154 -0.1521 0.4592 0.076 Uiso 1 1 calc R . . C21 C 1.1732(3) -0.0393(3) 0.42154(6) 0.0535(8) Uani 1 1 d . . . H21 H 1.1308 -0.0962 0.4067 0.064 Uiso 1 1 calc R . . C22 C 0.0958(3) 0.6764(3) 0.07152(6) 0.0433(6) Uani 1 1 d . . . C23 C 0.0409(3) 0.7662(3) 0.04963(6) 0.0480(7) Uani 1 1 d . . . C24 C -0.0248(3) 0.8876(3) 0.05883(6) 0.0476(7) Uani 1 1 d . . . C25 C -0.0342(3) 0.9196(3) 0.09001(7) 0.0475(7) Uani 1 1 d . . . C26 C 0.0207(3) 0.8272(3) 0.11149(6) 0.0419(6) Uani 1 1 d . . . C27 C 0.0884(2) 0.7040(3) 0.10322(6) 0.0381(6) Uani 1 1 d . . . C28 C 0.1484(3) 0.6032(3) 0.12664(6) 0.0403(6) Uani 1 1 d . . . C29 C 0.2873(3) 0.5839(3) 0.17174(6) 0.0462(7) Uani 1 1 d . . . H29A H 0.3453 0.5146 0.1621 0.055 Uiso 1 1 calc R . . H29B H 0.2243 0.5286 0.1834 0.055 Uiso 1 1 calc R . . C30 C 0.3620(3) 0.6791(3) 0.19397(6) 0.0519(8) Uani 1 1 d . . . H30A H 0.3046 0.7466 0.2043 0.062 Uiso 1 1 calc R . . H30B H 0.4249 0.7358 0.1826 0.062 Uiso 1 1 calc R . . C31 C 0.4287(3) 0.5840(3) 0.21786(6) 0.0524(8) Uani 1 1 d . . . H31A H 0.3646 0.5254 0.2284 0.063 Uiso 1 1 calc R . . H31B H 0.4854 0.5173 0.2070 0.063 Uiso 1 1 calc R . . C32 C 0.5055(3) 0.6650(3) 0.24212(6) 0.0533(8) Uani 1 1 d . . . C33 C 0.6008(3) 0.6487(3) 0.29459(6) 0.0587(9) Uani 1 1 d . . . H33A H 0.5650 0.6072 0.3135 0.070 Uiso 1 1 calc R . . H33B H 0.5871 0.7537 0.2953 0.070 Uiso 1 1 calc R . . C34 C 0.7413(3) 0.6196(3) 0.29426(6) 0.0559(8) Uani 1 1 d . . . H34A H 0.7790 0.6685 0.2764 0.067 Uiso 1 1 calc R . . H34B H 0.7556 0.5153 0.2919 0.067 Uiso 1 1 calc R . . C35 C 0.8075(3) 0.6723(3) 0.32394(6) 0.0542(8) Uani 1 1 d . . . H35A H 0.8993 0.6600 0.3217 0.065 Uiso 1 1 calc R . . H35B H 0.7907 0.7760 0.3265 0.065 Uiso 1 1 calc R . . C36 C 0.7652(3) 0.5929(3) 0.35295(6) 0.0430(7) Uani 1 1 d . . . C37 C 0.7645(3) 0.6161(3) 0.41040(6) 0.0425(6) Uani 1 1 d . . . C38 C 0.8222(3) 0.6979(3) 0.43409(6) 0.0535(8) Uani 1 1 d . . . H38 H 0.8707 0.7800 0.4291 0.064 Uiso 1 1 calc R . . C39 C 0.8076(3) 0.6577(4) 0.46460(7) 0.0671(10) Uani 1 1 d . . . H39 H 0.8466 0.7126 0.4803 0.081 Uiso 1 1 calc R . . C40 C 0.7364(4) 0.5378(4) 0.47230(7) 0.0702(10) Uani 1 1 d . . . H40 H 0.7269 0.5109 0.4931 0.084 Uiso 1 1 calc R . . C41 C 0.6787(3) 0.4570(4) 0.44900(7) 0.0621(8) Uani 1 1 d . . . H41 H 0.6305 0.3751 0.4542 0.075 Uiso 1 1 calc R . . C42 C 0.6911(3) 0.4956(3) 0.41801(6) 0.0515(7) Uani 1 1 d . . . H42 H 0.6506 0.4412 0.4025 0.062 Uiso 1 1 calc R . . H1 H 0.713(3) 0.206(2) 0.1506(6) 0.043(8) Uiso 1 1 d D . . H4 H 0.238(3) 0.754(2) 0.1468(6) 0.041(8) Uiso 1 1 d D . . H2 H 1.005(3) -0.093(2) 0.2660(6) 0.053(9) Uiso 1 1 d D . . H3 H 1.290(2) 0.206(2) 0.3772(6) 0.036(7) Uiso 1 1 d D . . H5 H 0.513(3) 0.499(2) 0.2681(7) 0.060(10) Uiso 1 1 d D . . H6 H 0.815(3) 0.749(2) 0.3781(7) 0.064(10) Uiso 1 1 d 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 N1 0.0575(16) 0.0346(13) 0.0445(13) 0.0004(10) -0.0177(11) 0.0044(11) N2 0.089(2) 0.0473(16) 0.0510(14) 0.0029(12) -0.0295(13) 0.0021(15) N3 0.0619(17) 0.0411(13) 0.0397(13) -0.0017(10) -0.0123(11) -0.0010(12) N4 0.0606(16) 0.0321(13) 0.0479(13) -0.0014(10) -0.0246(11) 0.0022(11) N5 0.083(2) 0.0427(15) 0.0443(13) 0.0002(11) -0.0265(13) 0.0033(14) N6 0.0573(16) 0.0362(13) 0.0422(12) -0.0050(10) -0.0150(11) -0.0012(12) O1 0.0798(15) 0.0408(12) 0.0550(12) -0.0016(9) -0.0204(10) -0.0054(10) O2 0.133(2) 0.0480(14) 0.0676(14) -0.0023(11) -0.0438(14) 0.0021(14) O3 0.0845(16) 0.0404(12) 0.0457(11) -0.0040(9) -0.0167(10) 0.0036(11) O4 0.0729(15) 0.0386(11) 0.0535(11) 0.0028(9) -0.0211(10) -0.0056(10) O5 0.117(2) 0.0429(13) 0.0681(14) 0.0002(10) -0.0432(13) -0.0078(13) O6 0.1017(18) 0.0347(11) 0.0487(11) -0.0023(8) -0.0255(11) -0.0045(11) F1 0.0815(13) 0.0667(11) 0.0517(10) -0.0142(8) -0.0075(9) 0.0135(10) F2 0.0911(15) 0.0974(15) 0.0361(9) -0.0005(9) -0.0126(8) -0.0017(11) F3 0.0764(13) 0.0835(13) 0.0594(10) 0.0265(9) -0.0242(9) 0.0060(10) F4 0.0697(13) 0.0687(12) 0.0740(12) 0.0084(9) -0.0093(9) 0.0264(10) F5 0.0645(11) 0.0628(10) 0.0425(9) -0.0026(7) -0.0051(7) 0.0175(9) F6 0.0809(13) 0.0587(10) 0.0502(9) -0.0115(8) -0.0108(8) 0.0162(10) F7 0.0878(14) 0.0927(14) 0.0369(9) 0.0016(8) -0.0175(8) 0.0074(11) F8 0.0677(13) 0.0856(13) 0.0670(11) 0.0299(10) -0.0243(9) 0.0106(10) F9 0.0628(12) 0.0627(11) 0.0827(12) 0.0029(9) -0.0098(9) 0.0254(10) F10 0.0640(11) 0.0692(11) 0.0447(9) -0.0061(8) -0.0051(8) 0.0176(9) C1 0.0457(17) 0.0482(16) 0.0454(15) -0.0044(12) -0.0117(12) -0.0041(13) C2 0.0489(18) 0.0630(19) 0.0383(15) 0.0023(13) -0.0092(12) -0.0067(15) C3 0.0413(17) 0.0615(19) 0.0482(16) 0.0166(14) -0.0174(13) -0.0059(15) C4 0.0388(16) 0.0496(16) 0.0544(17) 0.0060(13) -0.0099(13) 0.0048(13) C5 0.0380(16) 0.0513(16) 0.0376(14) 0.0036(12) -0.0069(11) -0.0022(13) C6 0.0379(15) 0.0405(14) 0.0399(14) 0.0018(11) -0.0109(11) -0.0015(12) C7 0.0461(17) 0.0406(16) 0.0419(14) 0.0005(12) -0.0072(12) -0.0008(13) C8 0.0564(18) 0.0410(15) 0.0447(15) -0.0002(12) -0.0119(13) 0.0116(13) C9 0.0591(19) 0.0464(16) 0.0464(16) 0.0001(12) -0.0150(13) 0.0068(14) C10 0.071(2) 0.0463(16) 0.0529(17) 0.0009(13) -0.0250(15) 0.0044(15) C11 0.070(2) 0.0466(18) 0.0426(15) 0.0053(13) -0.0154(14) 0.0005(15) C12 0.071(2) 0.068(2) 0.0407(15) 0.0016(14) -0.0175(14) 0.0021(17) C13 0.077(2) 0.0639(19) 0.0340(14) 0.0016(13) -0.0066(14) -0.0139(17) C14 0.081(2) 0.067(2) 0.0418(16) 0.0001(14) -0.0070(15) -0.0198(18) C15 0.0481(17) 0.0440(16) 0.0386(14) -0.0032(11) -0.0130(12) 0.0057(13) C16 0.0483(17) 0.0439(15) 0.0376(14) -0.0033(11) -0.0123(12) 0.0154(13) C17 0.068(2) 0.0500(17) 0.0438(16) -0.0089(13) -0.0135(14) 0.0103(15) C18 0.083(2) 0.072(2) 0.0422(17) -0.0151(15) -0.0194(16) 0.014(2) C19 0.084(3) 0.089(3) 0.0407(17) 0.0043(17) -0.0072(16) 0.013(2) C20 0.066(2) 0.072(2) 0.0520(18) 0.0095(16) -0.0034(15) 0.0026(18) C21 0.0551(19) 0.0600(19) 0.0451(16) -0.0018(14) -0.0110(13) 0.0046(15) C22 0.0420(16) 0.0447(15) 0.0429(14) -0.0026(12) -0.0101(12) -0.0005(13) C23 0.0464(17) 0.0601(18) 0.0374(14) 0.0059(13) -0.0118(12) -0.0046(15) C24 0.0392(16) 0.0530(17) 0.0504(16) 0.0159(13) -0.0176(13) -0.0032(14) C25 0.0370(16) 0.0475(16) 0.0579(17) 0.0041(13) -0.0085(13) 0.0039(13) C26 0.0391(16) 0.0465(15) 0.0401(14) -0.0006(12) -0.0082(11) 0.0003(13) C27 0.0350(15) 0.0399(14) 0.0394(13) 0.0025(11) -0.0086(11) -0.0039(12) C28 0.0465(16) 0.0357(15) 0.0386(14) 0.0013(11) -0.0057(11) -0.0001(12) C29 0.0589(19) 0.0366(14) 0.0430(14) 0.0008(11) -0.0168(13) 0.0073(13) C30 0.065(2) 0.0395(15) 0.0509(16) -0.0018(12) -0.0240(14) 0.0040(14) C31 0.069(2) 0.0411(15) 0.0466(15) 0.0029(12) -0.0246(14) -0.0035(14) C32 0.074(2) 0.0366(16) 0.0493(16) -0.0021(12) -0.0260(15) 0.0056(14) C33 0.078(2) 0.0569(18) 0.0411(15) -0.0082(13) -0.0232(15) 0.0094(17) C34 0.077(2) 0.0543(18) 0.0362(15) -0.0043(12) -0.0098(14) -0.0045(16) C35 0.064(2) 0.0529(17) 0.0451(16) -0.0029(13) -0.0120(14) -0.0057(15) C36 0.0544(18) 0.0323(14) 0.0421(14) -0.0047(11) -0.0209(12) 0.0080(12) C37 0.0481(17) 0.0414(15) 0.0378(14) -0.0046(11) -0.0128(12) 0.0121(13) C38 0.061(2) 0.0544(18) 0.0446(16) -0.0100(13) -0.0170(14) 0.0086(15) C39 0.075(2) 0.081(2) 0.0443(17) -0.0164(16) -0.0195(16) 0.019(2) C40 0.072(2) 0.094(3) 0.0450(18) 0.0038(18) -0.0079(16) 0.020(2) C41 0.060(2) 0.068(2) 0.0580(19) 0.0139(16) -0.0016(15) 0.0124(17) C42 0.0489(18) 0.0529(17) 0.0523(17) -0.0027(13) -0.0132(13) 0.0108(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 N1 C7 1.323(3) . ? N1 C8 1.446(3) . ? N1 H1 0.829(17) . ? N2 C11 1.320(4) . ? N2 C12 1.451(3) . ? N2 H2 0.829(17) . ? N3 C15 1.343(3) . ? N3 C16 1.409(3) . ? N3 H3 0.843(17) . ? N4 C28 1.318(3) . ? N4 C29 1.445(3) . ? N4 H4 0.814(17) . ? N5 C32 1.328(3) . ? N5 C33 1.454(3) . ? N5 H5 0.847(18) . ? N6 C36 1.337(3) . ? N6 C37 1.412(3) . ? N6 H6 0.828(18) . ? O1 C7 1.227(3) . ? O2 C11 1.218(3) . ? O3 C15 1.217(3) . ? O4 C28 1.223(3) . ? O5 C32 1.238(3) . ? O6 C36 1.220(3) . ? F1 C1 1.334(3) . ? F2 C2 1.334(3) . ? F3 C3 1.330(3) . ? F4 C4 1.338(3) . ? F5 C5 1.344(3) . ? F6 C22 1.338(3) . ? F7 C23 1.330(3) . ? F8 C24 1.332(3) . ? F9 C25 1.333(3) . ? F10 C26 1.340(3) . ? C1 C2 1.373(4) . ? C1 C6 1.384(4) . ? C2 C3 1.360(4) . ? C3 C4 1.374(4) . ? C4 C5 1.368(4) . ? C5 C6 1.378(4) . ? C6 C7 1.496(3) . ? C8 C9 1.507(3) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.510(3) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C11 1.506(4) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C12 C13 1.487(4) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C14 1.524(4) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 C15 1.498(4) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C16 C21 1.384(4) . ? C16 C17 1.385(4) . ? C17 C18 1.373(4) . ? C17 H17 0.9300 . ? C18 C19 1.365(5) . ? C18 H18 0.9300 . ? C19 C20 1.378(5) . ? C19 H19 0.9300 . ? C20 C21 1.382(4) . ? C20 H20 0.9300 . ? C21 H21 0.9300 . ? C22 C23 1.369(4) . ? C22 C27 1.385(3) . ? C23 C24 1.364(4) . ? C24 C25 1.372(4) . ? C25 C26 1.372(4) . ? C26 C27 1.377(4) . ? C27 C28 1.496(3) . ? C29 C30 1.504(3) . ? C29 H29A 0.9700 . ? C29 H29B 0.9700 . ? C30 C31 1.510(3) . ? C30 H30A 0.9700 . ? C30 H30B 0.9700 . ? C31 C32 1.503(3) . ? C31 H31A 0.9700 . ? C31 H31B 0.9700 . ? C33 C34 1.491(4) . ? C33 H33A 0.9700 . ? C33 H33B 0.9700 . ? C34 C35 1.522(3) . ? C34 H34A 0.9700 . ? C34 H34B 0.9700 . ? C35 C36 1.508(4) . ? C35 H35A 0.9700 . ? C35 H35B 0.9700 . ? C37 C42 1.382(4) . ? C37 C38 1.394(4) . ? C38 C39 1.368(4) . ? C38 H38 0.9300 . ? C39 C40 1.366(5) . ? C39 H39 0.9300 . ? C40 C41 1.377(5) . ? C40 H40 0.9300 . ? C41 C42 1.381(4) . ? C41 H41 0.9300 . ? C42 H42 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 C7 N1 C8 120.3(2) . . ? C7 N1 H1 120.0(18) . . ? C8 N1 H1 118.7(19) . . ? C11 N2 C12 123.3(3) . . ? C11 N2 H2 118(2) . . ? C12 N2 H2 118(2) . . ? C15 N3 C16 128.3(2) . . ? C15 N3 H3 112.7(17) . . ? C16 N3 H3 118.5(17) . . ? C28 N4 C29 121.9(2) . . ? C28 N4 H4 121.1(18) . . ? C29 N4 H4 116.9(19) . . ? C32 N5 C33 124.0(3) . . ? C32 N5 H5 118(2) . . ? C33 N5 H5 118(2) . . ? C36 N6 C37 128.0(2) . . ? C36 N6 H6 116(2) . . ? C37 N6 H6 115(2) . . ? F1 C1 C2 117.4(2) . . ? F1 C1 C6 120.2(2) . . ? C2 C1 C6 122.4(3) . . ? F2 C2 C3 119.4(3) . . ? F2 C2 C1 120.3(3) . . ? C3 C2 C1 120.3(3) . . ? F3 C3 C2 120.6(3) . . ? F3 C3 C4 120.2(3) . . ? C2 C3 C4 119.1(2) . . ? F4 C4 C5 120.7(3) . . ? F4 C4 C3 119.7(2) . . ? C5 C4 C3 119.6(3) . . ? F5 C5 C4 116.5(2) . . ? F5 C5 C6 120.3(2) . . ? C4 C5 C6 123.2(2) . . ? C5 C6 C1 115.4(2) . . ? C5 C6 C7 123.2(2) . . ? C1 C6 C7 121.3(2) . . ? O1 C7 N1 123.4(2) . . ? O1 C7 C6 121.1(2) . . ? N1 C7 C6 115.5(2) . . ? N1 C8 C9 112.4(2) . . ? N1 C8 H8A 109.1 . . ? C9 C8 H8A 109.1 . . ? N1 C8 H8B 109.1 . . ? C9 C8 H8B 109.1 . . ? H8A C8 H8B 107.9 . . ? C8 C9 C10 110.5(2) . . ? C8 C9 H9A 109.6 . . ? C10 C9 H9A 109.6 . . ? C8 C9 H9B 109.6 . . ? C10 C9 H9B 109.6 . . ? H9A C9 H9B 108.1 . . ? C11 C10 C9 114.0(2) . . ? C11 C10 H10A 108.7 . . ? C9 C10 H10A 108.7 . . ? C11 C10 H10B 108.7 . . ? C9 C10 H10B 108.7 . . ? H10A C10 H10B 107.6 . . ? O2 C11 N2 122.5(3) . . ? O2 C11 C10 122.1(2) . . ? N2 C11 C10 115.4(3) . . ? N2 C12 C13 112.9(3) . . ? N2 C12 H12A 109.0 . . ? C13 C12 H12A 109.0 . . ? N2 C12 H12B 109.0 . . ? C13 C12 H12B 109.0 . . ? H12A C12 H12B 107.8 . . ? C12 C13 C14 112.1(3) . . ? C12 C13 H13A 109.2 . . ? C14 C13 H13A 109.2 . . ? C12 C13 H13B 109.2 . . ? C14 C13 H13B 109.2 . . ? H13A C13 H13B 107.9 . . ? C15 C14 C13 114.5(2) . . ? C15 C14 H14A 108.6 . . ? C13 C14 H14A 108.6 . . ? C15 C14 H14B 108.6 . . ? C13 C14 H14B 108.6 . . ? H14A C14 H14B 107.6 . . ? O3 C15 N3 123.5(2) . . ? O3 C15 C14 122.1(2) . . ? N3 C15 C14 114.4(2) . . ? C21 C16 C17 119.7(3) . . ? C21 C16 N3 122.9(2) . . ? C17 C16 N3 117.3(3) . . ? C18 C17 C16 120.1(3) . . ? C18 C17 H17 120.0 . . ? C16 C17 H17 120.0 . . ? C19 C18 C17 120.7(3) . . ? C19 C18 H18 119.7 . . ? C17 C18 H18 119.7 . . ? C18 C19 C20 119.4(3) . . ? C18 C19 H19 120.3 . . ? C20 C19 H19 120.3 . . ? C19 C20 C21 120.9(3) . . ? C19 C20 H20 119.5 . . ? C21 C20 H20 119.5 . . ? C20 C21 C16 119.1(3) . . ? C20 C21 H21 120.4 . . ? C16 C21 H21 120.4 . . ? F6 C22 C23 117.9(2) . . ? F6 C22 C27 119.6(2) . . ? C23 C22 C27 122.5(3) . . ? F7 C23 C24 120.0(2) . . ? F7 C23 C22 120.1(3) . . ? C24 C23 C22 119.9(3) . . ? F8 C24 C23 119.9(3) . . ? F8 C24 C25 120.5(3) . . ? C23 C24 C25 119.6(2) . . ? F9 C25 C26 120.5(3) . . ? F9 C25 C24 120.1(2) . . ? C26 C25 C24 119.4(3) . . ? F10 C26 C25 117.5(2) . . ? F10 C26 C27 119.6(2) . . ? C25 C26 C27 122.9(2) . . ? C26 C27 C22 115.7(2) . . ? C26 C27 C28 122.9(2) . . ? C22 C27 C28 121.4(2) . . ? O4 C28 N4 123.8(2) . . ? O4 C28 C27 120.8(2) . . ? N4 C28 C27 115.4(2) . . ? N4 C29 C30 112.9(2) . . ? N4 C29 H29A 109.0 . . ? C30 C29 H29A 109.0 . . ? N4 C29 H29B 109.0 . . ? C30 C29 H29B 109.0 . . ? H29A C29 H29B 107.8 . . ? C29 C30 C31 109.3(2) . . ? C29 C30 H30A 109.8 . . ? C31 C30 H30A 109.8 . . ? C29 C30 H30B 109.8 . . ? C31 C30 H30B 109.8 . . ? H30A C30 H30B 108.3 . . ? C32 C31 C30 115.3(2) . . ? C32 C31 H31A 108.5 . . ? C30 C31 H31A 108.5 . . ? C32 C31 H31B 108.5 . . ? C30 C31 H31B 108.5 . . ? H31A C31 H31B 107.5 . . ? O5 C32 N5 122.4(2) . . ? O5 C32 C31 122.4(2) . . ? N5 C32 C31 115.2(2) . . ? N5 C33 C34 113.9(2) . . ? N5 C33 H33A 108.8 . . ? C34 C33 H33A 108.8 . . ? N5 C33 H33B 108.8 . . ? C34 C33 H33B 108.8 . . ? H33A C33 H33B 107.7 . . ? C33 C34 C35 112.1(2) . . ? C33 C34 H34A 109.2 . . ? C35 C34 H34A 109.2 . . ? C33 C34 H34B 109.2 . . ? C35 C34 H34B 109.2 . . ? H34A C34 H34B 107.9 . . ? C36 C35 C34 113.8(2) . . ? C36 C35 H35A 108.8 . . ? C34 C35 H35A 108.8 . . ? C36 C35 H35B 108.8 . . ? C34 C35 H35B 108.8 . . ? H35A C35 H35B 107.7 . . ? O6 C36 N6 123.8(3) . . ? O6 C36 C35 121.2(2) . . ? N6 C36 C35 115.0(2) . . ? C42 C37 C38 119.5(3) . . ? C42 C37 N6 124.1(2) . . ? C38 C37 N6 116.4(3) . . ? C39 C38 C37 120.1(3) . . ? C39 C38 H38 119.9 . . ? C37 C38 H38 119.9 . . ? C40 C39 C38 120.7(3) . . ? C40 C39 H39 119.7 . . ? C38 C39 H39 119.7 . . ? C39 C40 C41 119.4(3) . . ? C39 C40 H40 120.3 . . ? C41 C40 H40 120.3 . . ? C40 C41 C42 121.2(3) . . ? C40 C41 H41 119.4 . . ? C42 C41 H41 119.4 . . ? C41 C42 C37 119.1(3) . . ? C41 C42 H42 120.5 . . ? C37 C42 H42 120.5 . . ? 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 F1 C1 C2 F2 0.6(4) . . . . ? C6 C1 C2 F2 179.6(3) . . . . ? F1 C1 C2 C3 -179.9(3) . . . . ? C6 C1 C2 C3 -0.9(4) . . . . ? F2 C2 C3 F3 1.1(4) . . . . ? C1 C2 C3 F3 -178.4(2) . . . . ? F2 C2 C3 C4 -179.3(3) . . . . ? C1 C2 C3 C4 1.1(4) . . . . ? F3 C3 C4 F4 -1.4(4) . . . . ? C2 C3 C4 F4 179.0(3) . . . . ? F3 C3 C4 C5 178.5(2) . . . . ? C2 C3 C4 C5 -1.1(4) . . . . ? F4 C4 C5 F5 2.3(4) . . . . ? C3 C4 C5 F5 -177.6(2) . . . . ? F4 C4 C5 C6 -179.3(3) . . . . ? C3 C4 C5 C6 0.8(4) . . . . ? F5 C5 C6 C1 177.9(2) . . . . ? C4 C5 C6 C1 -0.5(4) . . . . ? F5 C5 C6 C7 1.1(4) . . . . ? C4 C5 C6 C7 -177.3(3) . . . . ? F1 C1 C6 C5 179.5(2) . . . . ? C2 C1 C6 C5 0.5(4) . . . . ? F1 C1 C6 C7 -3.6(4) . . . . ? C2 C1 C6 C7 177.4(3) . . . . ? C8 N1 C7 O1 2.1(5) . . . . ? C8 N1 C7 C6 -178.7(2) . . . . ? C5 C6 C7 O1 135.4(3) . . . . ? C1 C6 C7 O1 -41.2(4) . . . . ? C5 C6 C7 N1 -43.8(4) . . . . ? C1 C6 C7 N1 139.5(3) . . . . ? C7 N1 C8 C9 -179.9(3) . . . . ? N1 C8 C9 C10 -173.9(3) . . . . ? C8 C9 C10 C11 -176.2(3) . . . . ? C12 N2 C11 O2 -1.5(6) . . . . ? C12 N2 C11 C10 -179.8(3) . . . . ? C9 C10 C11 O2 0.8(5) . . . . ? C9 C10 C11 N2 179.1(3) . . . . ? C11 N2 C12 C13 -103.2(4) . . . . ? N2 C12 C13 C14 173.5(3) . . . . ? C12 C13 C14 C15 64.1(4) . . . . ? C16 N3 C15 O3 -1.0(5) . . . . ? C16 N3 C15 C14 179.1(3) . . . . ? C13 C14 C15 O3 19.8(4) . . . . ? C13 C14 C15 N3 -160.3(3) . . . . ? C15 N3 C16 C21 -22.6(4) . . . . ? C15 N3 C16 C17 159.6(3) . . . . ? C21 C16 C17 C18 0.7(4) . . . . ? N3 C16 C17 C18 178.5(3) . . . . ? C16 C17 C18 C19 0.0(5) . . . . ? C17 C18 C19 C20 -0.4(5) . . . . ? C18 C19 C20 C21 0.3(5) . . . . ? C19 C20 C21 C16 0.3(5) . . . . ? C17 C16 C21 C20 -0.8(4) . . . . ? N3 C16 C21 C20 -178.5(3) . . . . ? F6 C22 C23 F7 0.6(4) . . . . ? C27 C22 C23 F7 178.6(3) . . . . ? F6 C22 C23 C24 -178.5(3) . . . . ? C27 C22 C23 C24 -0.6(4) . . . . ? F7 C23 C24 F8 0.6(4) . . . . ? C22 C23 C24 F8 179.7(2) . . . . ? F7 C23 C24 C25 -178.4(3) . . . . ? C22 C23 C24 C25 0.8(4) . . . . ? F8 C24 C25 F9 -0.6(4) . . . . ? C23 C24 C25 F9 178.4(3) . . . . ? F8 C24 C25 C26 179.7(2) . . . . ? C23 C24 C25 C26 -1.3(4) . . . . ? F9 C25 C26 F10 2.1(4) . . . . ? C24 C25 C26 F10 -178.2(2) . . . . ? F9 C25 C26 C27 -178.1(2) . . . . ? C24 C25 C26 C27 1.6(4) . . . . ? F10 C26 C27 C22 178.5(2) . . . . ? C25 C26 C27 C22 -1.4(4) . . . . ? F10 C26 C27 C28 -0.2(4) . . . . ? C25 C26 C27 C28 180.0(2) . . . . ? F6 C22 C27 C26 178.8(2) . . . . ? C23 C22 C27 C26 0.8(4) . . . . ? F6 C22 C27 C28 -2.6(4) . . . . ? C23 C22 C27 C28 179.5(3) . . . . ? C29 N4 C28 O4 0.8(5) . . . . ? C29 N4 C28 C27 -180.0(2) . . . . ? C26 C27 C28 O4 127.3(3) . . . . ? C22 C27 C28 O4 -51.3(4) . . . . ? C26 C27 C28 N4 -52.0(4) . . . . ? C22 C27 C28 N4 129.5(3) . . . . ? C28 N4 C29 C30 -177.3(3) . . . . ? N4 C29 C30 C31 -178.7(3) . . . . ? C29 C30 C31 C32 -178.9(3) . . . . ? C33 N5 C32 O5 4.7(5) . . . . ? C33 N5 C32 C31 -177.5(3) . . . . ? C30 C31 C32 O5 -21.2(5) . . . . ? C30 C31 C32 N5 161.0(3) . . . . ? C32 N5 C33 C34 -94.5(4) . . . . ? N5 C33 C34 C35 -175.2(2) . . . . ? C33 C34 C35 C36 64.3(3) . . . . ? C37 N6 C36 O6 5.1(5) . . . . ? C37 N6 C36 C35 -173.8(3) . . . . ? C34 C35 C36 O6 24.0(4) . . . . ? C34 C35 C36 N6 -157.0(3) . . . . ? C36 N6 C37 C42 -18.4(4) . . . . ? C36 N6 C37 C38 163.2(3) . . . . ? C42 C37 C38 C39 0.9(4) . . . . ? N6 C37 C38 C39 179.4(3) . . . . ? C37 C38 C39 C40 -0.2(5) . . . . ? C38 C39 C40 C41 -0.1(5) . . . . ? C39 C40 C41 C42 -0.3(5) . . . . ? C40 C41 C42 C37 1.0(4) . . . . ? C38 C37 C42 C41 -1.3(4) . . . . ? N6 C37 C42 C41 -179.6(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N6 H6 O4 0.828(18) 2.130(19) 2.953(3) 173(3) 2_655 N5 H5 O5 0.847(18) 2.008(19) 2.847(3) 171(3) 2_645 N4 H4 O6 0.814(17) 2.025(17) 2.837(3) 175(3) 2_655 N3 H3 O1 0.843(17) 2.246(18) 3.075(3) 168(2) 2_755 N2 H2 O2 0.829(17) 2.098(19) 2.901(4) 163(3) 2_745 N1 H1 O3 0.829(17) 2.060(18) 2.875(3) 168(3) 2_755 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.343 _refine_diff_density_min -0.231 _refine_diff_density_rms 0.055 _database_code_depnum_ccdc_archive 'CCDC 965767' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_cd212303 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H13 F5 N2 O2' _chemical_formula_weight 372.29 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 6.303(6) _cell_length_b 7.483(7) _cell_length_c 17.132(15) _cell_angle_alpha 85.192(18) _cell_angle_beta 81.417(18) _cell_angle_gamma 83.941(18) _cell_volume 792.6(12) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1652 _cell_measurement_theta_min 5.530 _cell_measurement_theta_max 56.597 _exptl_crystal_description prismatic _exptl_crystal_colour colorless _exptl_crystal_size_max 0.321 _exptl_crystal_size_mid 0.212 _exptl_crystal_size_min 0.145 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.560 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 380 _exptl_absorpt_coefficient_mu 0.143 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.0907 _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 4193 _diffrn_reflns_av_R_equivalents 0.0359 _diffrn_reflns_av_sigmaI/netI 0.0658 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.20 _diffrn_reflns_theta_max 25.50 _reflns_number_total 2882 _reflns_number_gt 1989 _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^)+(0.1119P)^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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef ? _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2882 _refine_ls_number_parameters 244 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0886 _refine_ls_R_factor_gt 0.0565 _refine_ls_wR_factor_ref 0.1750 _refine_ls_wR_factor_gt 0.1549 _refine_ls_goodness_of_fit_ref 1.009 _refine_ls_restrained_S_all 1.009 _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 0.4580(2) 0.8163(2) 0.34271(8) 0.0577(5) Uani 1 1 d . . . F2 F 0.7008(3) 0.7056(3) 0.45590(9) 0.0755(6) Uani 1 1 d . . . F3 F 1.1183(3) 0.5668(3) 0.41857(9) 0.0715(6) Uani 1 1 d . . . F4 F 1.2895(2) 0.5397(2) 0.26426(9) 0.0626(5) Uani 1 1 d . . . F5 F 1.0571(2) 0.6587(2) 0.14942(8) 0.0586(5) Uani 1 1 d . . . N1 N 0.6322(3) 0.7001(3) 0.11654(11) 0.0419(5) Uani 1 1 d . . . N2 N 0.9619(4) 0.8524(3) -0.18418(11) 0.0451(6) Uani 1 1 d . . . O1 O 0.4893(3) 0.9473(2) 0.18118(11) 0.0550(5) Uani 1 1 d . . . O2 O 1.1934(3) 0.6707(2) -0.11529(10) 0.0538(5) Uani 1 1 d . . . C1 C 0.6084(3) 0.8054(3) 0.17634(13) 0.0380(6) Uani 1 1 d . . . C2 C 0.7463(4) 0.7413(3) 0.24116(13) 0.0373(6) Uani 1 1 d . . . C3 C 0.6644(4) 0.7528(3) 0.32051(13) 0.0421(6) Uani 1 1 d . . . C4 C 0.7877(4) 0.6943(4) 0.37997(14) 0.0502(7) Uani 1 1 d . . . C5 C 0.9978(4) 0.6232(4) 0.36104(15) 0.0503(7) Uani 1 1 d . . . C6 C 1.0851(4) 0.6103(3) 0.28333(15) 0.0449(6) Uani 1 1 d . . . C7 C 0.9591(4) 0.6695(3) 0.22474(13) 0.0406(6) Uani 1 1 d . . . C8 C 0.5305(4) 0.7488(3) 0.04528(13) 0.0447(6) Uani 1 1 d . . . H8A H 0.4832 0.8765 0.0429 0.054 Uiso 1 1 calc R . . H8B H 0.4045 0.6833 0.0479 0.054 Uiso 1 1 calc R . . C9 C 0.6852(4) 0.7059(4) -0.02907(14) 0.0462(6) Uani 1 1 d . . . H9A H 0.6082 0.7277 -0.0744 0.055 Uiso 1 1 calc R . . H9B H 0.7367 0.5791 -0.0254 0.055 Uiso 1 1 calc R . . C10 C 0.8784(4) 0.8177(3) -0.04230(13) 0.0427(6) Uani 1 1 d . . . H10A H 0.8275 0.9446 -0.0457 0.051 Uiso 1 1 calc R . . H10B H 0.9571 0.7949 0.0026 0.051 Uiso 1 1 calc R . . C11 C 1.0286(4) 0.7736(3) -0.11709(13) 0.0388(6) Uani 1 1 d . . . C12 C 1.0570(4) 0.8286(3) -0.26369(14) 0.0404(6) Uani 1 1 d . . . C13 C 0.9227(4) 0.8704(4) -0.32172(15) 0.0517(7) Uani 1 1 d . . . H13 H 0.7777 0.9078 -0.3074 0.062 Uiso 1 1 calc R . . C14 C 1.0050(5) 0.8561(4) -0.40026(16) 0.0618(8) Uani 1 1 d . . . H14 H 0.9152 0.8844 -0.4388 0.074 Uiso 1 1 calc R . . C15 C 1.2199(5) 0.8001(5) -0.42224(16) 0.0640(8) Uani 1 1 d . . . H15 H 1.2752 0.7913 -0.4754 0.077 Uiso 1 1 calc R . . C16 C 1.3524(5) 0.7570(4) -0.36432(16) 0.0584(8) Uani 1 1 d . . . H16 H 1.4967 0.7176 -0.3790 0.070 Uiso 1 1 calc R . . C17 C 1.2734(4) 0.7718(4) -0.28496(15) 0.0490(7) Uani 1 1 d . . . H17 H 1.3638 0.7442 -0.2465 0.059 Uiso 1 1 calc R . . H1 H 0.704(4) 0.588(4) 0.1164(15) 0.051(7) Uiso 1 1 d . . . H2 H 0.837(5) 0.912(4) -0.1780(16) 0.060(8) Uiso 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 F1 0.0419(8) 0.0729(11) 0.0520(8) -0.0062(7) 0.0015(6) 0.0135(7) F2 0.0698(11) 0.1156(16) 0.0369(8) -0.0021(8) -0.0036(7) 0.0032(11) F3 0.0612(10) 0.0986(14) 0.0561(9) 0.0111(9) -0.0278(8) -0.0001(9) F4 0.0341(8) 0.0793(12) 0.0718(10) -0.0022(8) -0.0113(7) 0.0088(8) F5 0.0391(8) 0.0865(12) 0.0463(8) -0.0071(8) 0.0010(6) 0.0034(8) N1 0.0438(11) 0.0403(12) 0.0391(10) 0.0009(9) -0.0084(8) 0.0090(9) N2 0.0390(11) 0.0493(12) 0.0431(11) -0.0013(9) -0.0050(9) 0.0117(10) O1 0.0562(11) 0.0465(11) 0.0610(11) -0.0105(8) -0.0180(8) 0.0199(9) O2 0.0462(10) 0.0526(11) 0.0571(10) 0.0034(8) -0.0091(8) 0.0176(9) C1 0.0338(12) 0.0372(12) 0.0405(11) 0.0016(10) -0.0039(9) 0.0029(10) C2 0.0367(12) 0.0327(12) 0.0422(12) -0.0012(10) -0.0074(10) -0.0006(10) C3 0.0386(13) 0.0407(13) 0.0446(13) -0.0038(10) -0.0021(10) 0.0033(10) C4 0.0498(15) 0.0622(17) 0.0375(12) 0.0009(11) -0.0058(11) -0.0036(13) C5 0.0451(15) 0.0572(16) 0.0498(14) 0.0069(12) -0.0174(11) -0.0044(12) C6 0.0309(12) 0.0470(14) 0.0560(14) -0.0003(11) -0.0090(10) 0.0009(10) C7 0.0369(13) 0.0419(13) 0.0416(12) -0.0022(10) -0.0028(10) -0.0018(10) C8 0.0382(13) 0.0502(15) 0.0449(13) 0.0024(11) -0.0099(10) 0.0016(11) C9 0.0449(14) 0.0525(15) 0.0421(13) -0.0025(11) -0.0107(10) -0.0034(12) C10 0.0425(13) 0.0430(14) 0.0432(12) -0.0043(11) -0.0100(10) 0.0000(11) C11 0.0362(12) 0.0333(12) 0.0462(12) 0.0001(10) -0.0083(10) 0.0017(10) C12 0.0414(13) 0.0336(12) 0.0446(12) -0.0013(10) -0.0059(10) 0.0033(10) C13 0.0430(14) 0.0585(17) 0.0510(14) 0.0032(12) -0.0103(11) 0.0072(12) C14 0.0622(18) 0.073(2) 0.0499(15) 0.0025(14) -0.0173(13) 0.0008(15) C15 0.0646(19) 0.077(2) 0.0475(15) -0.0064(14) 0.0008(13) -0.0046(16) C16 0.0449(15) 0.0693(19) 0.0575(16) -0.0077(14) 0.0007(12) 0.0022(13) C17 0.0389(14) 0.0578(16) 0.0494(14) -0.0046(12) -0.0069(10) 0.0013(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag F1 C3 1.347(3) . ? F2 C4 1.340(3) . ? F3 C5 1.346(3) . ? F4 C6 1.344(3) . ? F5 C7 1.350(3) . ? N1 C1 1.326(3) . ? N1 C8 1.464(3) . ? N1 H1 0.91(3) . ? N2 C11 1.350(3) . ? N2 C12 1.422(3) . ? N2 H2 0.86(3) . ? O1 C1 1.235(3) . ? O2 C11 1.229(3) . ? C1 C2 1.526(3) . ? C2 C3 1.386(3) . ? C2 C7 1.388(3) . ? C3 C4 1.386(4) . ? C4 C5 1.376(4) . ? C5 C6 1.370(4) . ? C6 C7 1.387(3) . ? C8 C9 1.519(3) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.528(4) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C11 1.513(3) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C12 C17 1.388(4) . ? C12 C13 1.395(4) . ? C13 C14 1.377(4) . ? C13 H13 0.9300 . ? C14 C15 1.381(4) . ? C14 H14 0.9300 . ? C15 C16 1.387(4) . ? C15 H15 0.9300 . ? C16 C17 1.386(4) . ? C16 H16 0.9300 . ? C17 H17 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 C8 122.7(2) . . ? C1 N1 H1 124.6(17) . . ? C8 N1 H1 112.6(17) . . ? C11 N2 C12 128.2(2) . . ? C11 N2 H2 115.1(18) . . ? C12 N2 H2 116.0(19) . . ? O1 C1 N1 124.8(2) . . ? O1 C1 C2 120.4(2) . . ? N1 C1 C2 114.84(19) . . ? C3 C2 C7 116.1(2) . . ? C3 C2 C1 121.3(2) . . ? C7 C2 C1 122.6(2) . . ? F1 C3 C4 117.4(2) . . ? F1 C3 C2 120.7(2) . . ? C4 C3 C2 121.8(2) . . ? F2 C4 C5 120.1(2) . . ? F2 C4 C3 119.8(2) . . ? C5 C4 C3 120.1(2) . . ? F3 C5 C6 119.8(2) . . ? F3 C5 C4 120.3(2) . . ? C6 C5 C4 119.9(2) . . ? F4 C6 C5 120.3(2) . . ? F4 C6 C7 120.5(2) . . ? C5 C6 C7 119.1(2) . . ? F5 C7 C6 116.1(2) . . ? F5 C7 C2 121.0(2) . . ? C6 C7 C2 122.9(2) . . ? N1 C8 C9 111.37(19) . . ? N1 C8 H8A 109.4 . . ? C9 C8 H8A 109.4 . . ? N1 C8 H8B 109.4 . . ? C9 C8 H8B 109.4 . . ? H8A C8 H8B 108.0 . . ? C8 C9 C10 112.9(2) . . ? C8 C9 H9A 109.0 . . ? C10 C9 H9A 109.0 . . ? C8 C9 H9B 109.0 . . ? C10 C9 H9B 109.0 . . ? H9A C9 H9B 107.8 . . ? C11 C10 C9 111.8(2) . . ? C11 C10 H10A 109.2 . . ? C9 C10 H10A 109.2 . . ? C11 C10 H10B 109.2 . . ? C9 C10 H10B 109.2 . . ? H10A C10 H10B 107.9 . . ? O2 C11 N2 124.2(2) . . ? O2 C11 C10 121.53(19) . . ? N2 C11 C10 114.3(2) . . ? C17 C12 C13 120.1(2) . . ? C17 C12 N2 123.2(2) . . ? C13 C12 N2 116.6(2) . . ? C14 C13 C12 120.0(2) . . ? C14 C13 H13 120.0 . . ? C12 C13 H13 120.0 . . ? C13 C14 C15 120.5(3) . . ? C13 C14 H14 119.7 . . ? C15 C14 H14 119.7 . . ? C14 C15 C16 119.4(3) . . ? C14 C15 H15 120.3 . . ? C16 C15 H15 120.3 . . ? C17 C16 C15 121.1(3) . . ? C17 C16 H16 119.5 . . ? C15 C16 H16 119.5 . . ? C16 C17 C12 119.0(2) . . ? C16 C17 H17 120.5 . . ? C12 C17 H17 120.5 . . ? 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 C8 N1 C1 O1 5.0(4) . . . . ? C8 N1 C1 C2 -173.60(19) . . . . ? O1 C1 C2 C3 42.0(3) . . . . ? N1 C1 C2 C3 -139.3(2) . . . . ? O1 C1 C2 C7 -137.7(3) . . . . ? N1 C1 C2 C7 41.0(3) . . . . ? C7 C2 C3 F1 -178.3(2) . . . . ? C1 C2 C3 F1 1.9(4) . . . . ? C7 C2 C3 C4 -0.5(4) . . . . ? C1 C2 C3 C4 179.7(2) . . . . ? F1 C3 C4 F2 -1.2(4) . . . . ? C2 C3 C4 F2 -179.0(2) . . . . ? F1 C3 C4 C5 178.1(2) . . . . ? C2 C3 C4 C5 0.2(4) . . . . ? F2 C4 C5 F3 -0.9(4) . . . . ? C3 C4 C5 F3 179.8(2) . . . . ? F2 C4 C5 C6 179.4(2) . . . . ? C3 C4 C5 C6 0.1(4) . . . . ? F3 C5 C6 F4 0.8(4) . . . . ? C4 C5 C6 F4 -179.4(3) . . . . ? F3 C5 C6 C7 -179.8(2) . . . . ? C4 C5 C6 C7 -0.1(4) . . . . ? F4 C6 C7 F5 -2.8(4) . . . . ? C5 C6 C7 F5 177.9(2) . . . . ? F4 C6 C7 C2 179.1(2) . . . . ? C5 C6 C7 C2 -0.3(4) . . . . ? C3 C2 C7 F5 -177.5(2) . . . . ? C1 C2 C7 F5 2.2(4) . . . . ? C3 C2 C7 C6 0.6(4) . . . . ? C1 C2 C7 C6 -179.7(2) . . . . ? C1 N1 C8 C9 137.1(2) . . . . ? N1 C8 C9 C10 -64.7(3) . . . . ? C8 C9 C10 C11 -179.43(17) . . . . ? C12 N2 C11 O2 3.1(4) . . . . ? C12 N2 C11 C10 -175.1(2) . . . . ? C9 C10 C11 O2 -98.9(3) . . . . ? C9 C10 C11 N2 79.4(3) . . . . ? C11 N2 C12 C17 -24.3(4) . . . . ? C11 N2 C12 C13 157.5(3) . . . . ? C17 C12 C13 C14 -0.3(4) . . . . ? N2 C12 C13 C14 178.0(2) . . . . ? C12 C13 C14 C15 0.2(5) . . . . ? C13 C14 C15 C16 0.4(5) . . . . ? C14 C15 C16 C17 -0.9(5) . . . . ? C15 C16 C17 C12 0.9(4) . . . . ? C13 C12 C17 C16 -0.2(4) . . . . ? N2 C12 C17 C16 -178.4(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2 O1 0.86(3) 2.22(3) 3.067(4) 171(3) 2_675 N1 H1 O2 0.91(3) 1.97(3) 2.875(3) 170(2) 2_765 _diffrn_measured_fraction_theta_max 0.978 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.978 _refine_diff_density_max 0.332 _refine_diff_density_min -0.273 _refine_diff_density_rms 0.074 _database_code_depnum_ccdc_archive 'CCDC 965768' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_a11213b _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H9 F5 N2 O2' _chemical_formula_weight 344.24 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 6.214(6) _cell_length_b 7.246(7) _cell_length_c 15.518(14) _cell_angle_alpha 93.009(12) _cell_angle_beta 96.517(12) _cell_angle_gamma 95.237(13) _cell_volume 689.9(11) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 587 _cell_measurement_theta_min 2.647 _cell_measurement_theta_max 25.668 _exptl_crystal_description sheet _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.657 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 348 _exptl_absorpt_coefficient_mu 0.157 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9694 _exptl_absorpt_correction_T_max 0.9922 _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 2884 _diffrn_reflns_av_R_equivalents 0.0336 _diffrn_reflns_av_sigmaI/netI 0.0416 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.32 _diffrn_reflns_theta_max 25.01 _reflns_number_total 2396 _reflns_number_gt 1852 _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^)+(0.1777P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2396 _refine_ls_number_parameters 225 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.1059 _refine_ls_R_factor_gt 0.0890 _refine_ls_wR_factor_ref 0.2584 _refine_ls_wR_factor_gt 0.2421 _refine_ls_goodness_of_fit_ref 1.091 _refine_ls_restrained_S_all 1.092 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group F1 F 0.3427(4) 0.6759(3) 1.32207(14) 0.0472(7) Uani 1 1 d . . . F2 F 0.6676(4) 0.7942(4) 1.44379(15) 0.0601(8) Uani 1 1 d . . . F3 F 1.0578(4) 0.9289(4) 1.40073(17) 0.0599(8) Uani 1 1 d . . . F4 F 1.1178(4) 0.9488(4) 1.23061(17) 0.0553(8) Uani 1 1 d . . . F5 F 0.8036(4) 0.8191(4) 1.10681(15) 0.0531(8) Uani 1 1 d . . . O1 O 0.2517(5) 0.5349(4) 1.15025(19) 0.0502(9) Uani 1 1 d . . . O2 O 0.4697(5) 0.8462(4) 0.91292(17) 0.0484(8) Uani 1 1 d . . . N1 N 0.3553(6) 0.7649(6) 1.0688(2) 0.0483(10) Uani 1 1 d D . . H1 H 0.422(6) 0.873(5) 1.070(2) 0.027(9) Uiso 1 1 d D . . N2 N 0.1807(6) 0.6702(5) 0.83923(19) 0.0388(8) Uani 1 1 d D . . H2 H 0.065(7) 0.614(5) 0.848(3) 0.037(11) Uiso 1 1 d D . . C1 C 0.5326(6) 0.7380(5) 1.2958(2) 0.0342(9) Uani 1 1 d . . . C2 C 0.6986(7) 0.8001(6) 1.3602(2) 0.0404(10) Uani 1 1 d . . . C3 C 0.8970(6) 0.8687(6) 1.3388(3) 0.0413(10) Uani 1 1 d . . . C4 C 0.9276(6) 0.8776(5) 1.2532(3) 0.0393(10) Uani 1 1 d . . . C5 C 0.7598(6) 0.8136(5) 1.1895(2) 0.0358(9) Uani 1 1 d . . . C6 C 0.5565(6) 0.7444(5) 1.2084(2) 0.0334(9) Uani 1 1 d . . . C7 C 0.3727(6) 0.6716(5) 1.1400(2) 0.0336(9) Uani 1 1 d . . . C8 C 0.2040(8) 0.7000(8) 0.9944(3) 0.0591(14) Uani 1 1 d . . . H8A H 0.0695 0.7575 0.9968 0.071 Uiso 1 1 calc R . . H8B H 0.1708 0.5666 0.9946 0.071 Uiso 1 1 calc R . . C9 C 0.3004(6) 0.7477(5) 0.9113(2) 0.0361(9) Uani 1 1 d . . . C10 C 0.2217(6) 0.6864(5) 0.7518(2) 0.0320(8) Uani 1 1 d . . . C11 C 0.4248(7) 0.7414(6) 0.7282(2) 0.0400(9) Uani 1 1 d . . . H11 H 0.5437 0.7717 0.7702 0.048 Uiso 1 1 calc R . . C12 C 0.4475(7) 0.7503(6) 0.6408(3) 0.0464(11) Uani 1 1 d . . . H12 H 0.5831 0.7885 0.6244 0.056 Uiso 1 1 calc R . . C13 C 0.2751(7) 0.7042(7) 0.5779(3) 0.0494(11) Uani 1 1 d . . . H13 H 0.2941 0.7092 0.5194 0.059 Uiso 1 1 calc R . . C14 C 0.0728(8) 0.6503(6) 0.6022(3) 0.0497(11) Uani 1 1 d . . . H14 H -0.0458 0.6201 0.5600 0.060 Uiso 1 1 calc R . . C15 C 0.0468(7) 0.6413(5) 0.6894(2) 0.0393(9) Uani 1 1 d . . . H15 H -0.0893 0.6046 0.7057 0.047 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 0.0433(13) 0.0593(16) 0.0403(13) 0.0084(11) 0.0160(10) -0.0044(11) F2 0.0623(17) 0.088(2) 0.0296(12) 0.0043(12) 0.0046(11) 0.0049(14) F3 0.0468(15) 0.0744(19) 0.0527(15) -0.0016(13) -0.0135(12) 0.0020(13) F4 0.0331(13) 0.0658(17) 0.0671(17) 0.0072(13) 0.0114(12) -0.0028(11) F5 0.0464(14) 0.0748(18) 0.0407(13) 0.0057(12) 0.0202(11) 0.0009(12) O1 0.0528(18) 0.0446(17) 0.0495(17) 0.0102(13) 0.0034(14) -0.0160(14) O2 0.0511(18) 0.0568(19) 0.0328(14) -0.0038(12) 0.0096(12) -0.0200(14) N1 0.055(2) 0.056(2) 0.0282(17) 0.0047(15) 0.0029(15) -0.0256(19) N2 0.0371(18) 0.046(2) 0.0295(17) 0.0028(14) 0.0012(14) -0.0109(15) C1 0.0337(19) 0.035(2) 0.0358(19) 0.0042(15) 0.0083(16) 0.0053(16) C2 0.047(2) 0.044(2) 0.0321(19) 0.0043(16) 0.0048(17) 0.0115(18) C3 0.038(2) 0.041(2) 0.044(2) 0.0010(17) -0.0011(17) 0.0084(17) C4 0.0288(19) 0.037(2) 0.054(2) 0.0048(18) 0.0101(17) 0.0050(16) C5 0.040(2) 0.034(2) 0.0360(19) 0.0019(15) 0.0101(16) 0.0066(16) C6 0.036(2) 0.0295(19) 0.0356(19) 0.0031(15) 0.0088(16) 0.0018(15) C7 0.039(2) 0.0304(19) 0.0316(19) -0.0006(14) 0.0118(16) -0.0028(16) C8 0.055(3) 0.087(4) 0.029(2) 0.003(2) 0.0065(19) -0.028(2) C9 0.041(2) 0.040(2) 0.0273(18) 0.0023(15) 0.0093(15) -0.0059(17) C10 0.040(2) 0.0239(17) 0.0328(18) -0.0006(14) 0.0097(16) 0.0027(15) C11 0.038(2) 0.045(2) 0.036(2) 0.0037(17) 0.0028(16) 0.0027(17) C12 0.045(2) 0.058(3) 0.039(2) 0.0080(19) 0.0151(19) 0.008(2) C13 0.055(3) 0.065(3) 0.030(2) 0.0034(18) 0.0082(19) 0.009(2) C14 0.056(3) 0.058(3) 0.033(2) -0.0045(18) -0.0013(19) 0.007(2) C15 0.040(2) 0.044(2) 0.0325(19) -0.0008(16) 0.0030(16) -0.0007(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 F1 C1 1.338(4) . ? F2 C2 1.334(4) . ? F3 C3 1.330(5) . ? F4 C4 1.337(4) . ? F5 C5 1.343(4) . ? O1 C7 1.217(4) . ? O2 C9 1.213(4) . ? N1 C7 1.323(5) . ? N1 C8 1.434(5) . ? N1 H1 0.85(4) . ? N2 C9 1.338(5) . ? N2 C10 1.418(5) . ? N2 H2 0.82(4) . ? C1 C2 1.378(6) . ? C1 C6 1.384(5) . ? C2 C3 1.370(6) . ? C3 C4 1.368(6) . ? C4 C5 1.382(6) . ? C5 C6 1.384(5) . ? C6 C7 1.506(5) . ? C8 C9 1.525(5) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C10 C15 1.374(5) . ? C10 C11 1.383(5) . ? C11 C12 1.382(5) . ? C11 H11 0.9300 . ? C12 C13 1.370(6) . ? C12 H12 0.9300 . ? C13 C14 1.382(6) . ? C13 H13 0.9300 . ? C14 C15 1.385(6) . ? C14 H14 0.9300 . ? C15 H15 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 C7 N1 C8 121.6(3) . . ? C7 N1 H1 119(2) . . ? C8 N1 H1 118(2) . . ? C9 N2 C10 128.0(3) . . ? C9 N2 H2 114(3) . . ? C10 N2 H2 117(3) . . ? F1 C1 C2 116.5(3) . . ? F1 C1 C6 121.2(3) . . ? C2 C1 C6 122.3(3) . . ? F2 C2 C3 119.5(3) . . ? F2 C2 C1 120.4(4) . . ? C3 C2 C1 120.1(4) . . ? F3 C3 C4 120.2(4) . . ? F3 C3 C2 120.4(4) . . ? C4 C3 C2 119.4(4) . . ? F4 C4 C3 120.6(4) . . ? F4 C4 C5 119.7(4) . . ? C3 C4 C5 119.6(4) . . ? F5 C5 C4 116.6(3) . . ? F5 C5 C6 120.8(3) . . ? C4 C5 C6 122.6(4) . . ? C1 C6 C5 115.8(3) . . ? C1 C6 C7 120.8(3) . . ? C5 C6 C7 123.4(3) . . ? O1 C7 N1 123.3(3) . . ? O1 C7 C6 121.3(3) . . ? N1 C7 C6 115.4(3) . . ? N1 C8 C9 110.0(3) . . ? N1 C8 H8A 109.7 . . ? C9 C8 H8A 109.7 . . ? N1 C8 H8B 109.7 . . ? C9 C8 H8B 109.7 . . ? H8A C8 H8B 108.2 . . ? O2 C9 N2 125.0(3) . . ? O2 C9 C8 121.7(3) . . ? N2 C9 C8 113.3(3) . . ? C15 C10 C11 120.4(3) . . ? C15 C10 N2 116.2(3) . . ? C11 C10 N2 123.4(3) . . ? C12 C11 C10 118.6(4) . . ? C12 C11 H11 120.7 . . ? C10 C11 H11 120.7 . . ? C13 C12 C11 121.6(4) . . ? C13 C12 H12 119.2 . . ? C11 C12 H12 119.2 . . ? C12 C13 C14 119.2(4) . . ? C12 C13 H13 120.4 . . ? C14 C13 H13 120.4 . . ? C13 C14 C15 119.9(4) . . ? C13 C14 H14 120.0 . . ? C15 C14 H14 120.0 . . ? C10 C15 C14 120.1(4) . . ? C10 C15 H15 119.9 . . ? C14 C15 H15 119.9 . . ? 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 F1 C1 C2 F2 0.9(6) . . . . ? C6 C1 C2 F2 178.9(3) . . . . ? F1 C1 C2 C3 -178.9(3) . . . . ? C6 C1 C2 C3 -1.0(6) . . . . ? F2 C2 C3 F3 0.1(6) . . . . ? C1 C2 C3 F3 179.9(4) . . . . ? F2 C2 C3 C4 -178.9(4) . . . . ? C1 C2 C3 C4 1.0(6) . . . . ? F3 C3 C4 F4 -0.9(6) . . . . ? C2 C3 C4 F4 178.1(3) . . . . ? F3 C3 C4 C5 179.6(3) . . . . ? C2 C3 C4 C5 -1.4(6) . . . . ? F4 C4 C5 F5 3.2(5) . . . . ? C3 C4 C5 F5 -177.2(3) . . . . ? F4 C4 C5 C6 -177.6(3) . . . . ? C3 C4 C5 C6 1.9(6) . . . . ? F1 C1 C6 C5 179.2(3) . . . . ? C2 C1 C6 C5 1.3(6) . . . . ? F1 C1 C6 C7 -3.4(6) . . . . ? C2 C1 C6 C7 178.7(3) . . . . ? F5 C5 C6 C1 177.3(3) . . . . ? C4 C5 C6 C1 -1.8(6) . . . . ? F5 C5 C6 C7 0.0(6) . . . . ? C4 C5 C6 C7 -179.1(4) . . . . ? C8 N1 C7 O1 -6.3(7) . . . . ? C8 N1 C7 C6 172.9(4) . . . . ? C1 C6 C7 O1 -36.5(6) . . . . ? C5 C6 C7 O1 140.7(4) . . . . ? C1 C6 C7 N1 144.3(4) . . . . ? C5 C6 C7 N1 -38.5(5) . . . . ? C7 N1 C8 C9 -144.9(4) . . . . ? C10 N2 C9 O2 -0.7(7) . . . . ? C10 N2 C9 C8 179.6(4) . . . . ? N1 C8 C9 O2 -8.1(7) . . . . ? N1 C8 C9 N2 171.6(4) . . . . ? C9 N2 C10 C15 -161.1(4) . . . . ? C9 N2 C10 C11 19.8(7) . . . . ? C15 C10 C11 C12 0.2(6) . . . . ? N2 C10 C11 C12 179.2(4) . . . . ? C10 C11 C12 C13 -0.7(7) . . . . ? C11 C12 C13 C14 1.0(7) . . . . ? C12 C13 C14 C15 -0.8(7) . . . . ? C11 C10 C15 C14 0.1(6) . . . . ? N2 C10 C15 C14 -179.0(4) . . . . ? C13 C14 C15 C10 0.2(7) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2 O1 0.82(4) 2.16(4) 2.975(5) 172(4) 2_567 N1 H1 O2 0.85(4) 2.08(4) 2.914(5) 167(4) 2_677 _diffrn_measured_fraction_theta_max 0.979 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.979 _refine_diff_density_max 0.571 _refine_diff_density_min -0.367 _refine_diff_density_rms 0.129 _database_code_depnum_ccdc_archive 'CCDC 965769' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_dm13126 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H28 F5 N3 O3' _chemical_formula_weight 513.50 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 18.850(3) _cell_length_b 9.5190(13) _cell_length_c 13.5917(19) _cell_angle_alpha 90.00 _cell_angle_beta 100.231(2) _cell_angle_gamma 90.00 _cell_volume 2400.1(6) _cell_formula_units_Z 4 _cell_measurement_temperature 140(2) _cell_measurement_reflns_used 8125 _cell_measurement_theta_min 2.40 _cell_measurement_theta_max 30.52 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.421 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1072 _exptl_absorpt_coefficient_mu 0.120 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9649 _exptl_absorpt_correction_T_max 0.9964 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 140(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' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 16414 _diffrn_reflns_av_R_equivalents 0.0516 _diffrn_reflns_av_sigmaI/netI 0.0426 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.40 _diffrn_reflns_theta_max 26.00 _reflns_number_total 4702 _reflns_number_gt 3951 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.1163P)^2^+10.8368P] 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 0.0053(16) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4702 _refine_ls_number_parameters 326 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0922 _refine_ls_R_factor_gt 0.0811 _refine_ls_wR_factor_ref 0.3173 _refine_ls_wR_factor_gt 0.3056 _refine_ls_goodness_of_fit_ref 1.233 _refine_ls_restrained_S_all 1.233 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group F1 F 0.85200(18) 0.1129(3) -0.3892(2) 0.0375(8) Uani 1 1 d . . . F2 F 0.96305(18) 0.2674(3) -0.4291(2) 0.0376(8) Uani 1 1 d . . . F3 F 1.02187(17) 0.4701(4) -0.2995(3) 0.0451(9) Uani 1 1 d . . . F4 F 0.9696(2) 0.5162(4) -0.1292(3) 0.0516(10) Uani 1 1 d . . . F5 F 0.85860(17) 0.3654(3) -0.0882(2) 0.0385(8) Uani 1 1 d . . . O1 O 0.7976(2) 0.0100(4) -0.2194(3) 0.0327(8) Uani 1 1 d . . . O2 O 0.5092(2) 0.3500(4) 0.2177(3) 0.0350(9) Uani 1 1 d . . . O3 O 0.2736(2) 0.0029(3) 0.7226(3) 0.0323(8) Uani 1 1 d . . . N1 N 0.7389(2) 0.2041(4) -0.1799(3) 0.0267(9) Uani 1 1 d . . . H1 H 0.7358 0.2961 -0.1851 0.032 Uiso 1 1 calc R . . N2 N 0.4765(2) 0.1507(4) 0.2845(3) 0.0293(9) Uani 1 1 d . . . H2 H 0.4774 0.0582 0.2849 0.035 Uiso 1 1 calc R . . N3 N 0.2199(2) 0.2081(4) 0.7555(3) 0.0274(9) Uani 1 1 d . . . H3 H 0.2143 0.2961 0.7358 0.033 Uiso 1 1 calc R . . C1 C 0.8813(3) 0.2102(5) -0.3229(3) 0.0278(10) Uani 1 1 d . . . C2 C 0.9370(3) 0.2872(5) -0.3446(4) 0.0290(11) Uani 1 1 d . . . C3 C 0.9677(3) 0.3913(6) -0.2788(4) 0.0326(11) Uani 1 1 d . . . C4 C 0.9396(3) 0.4161(6) -0.1933(4) 0.0327(11) Uani 1 1 d . . . C5 C 0.8830(3) 0.3382(5) -0.1738(3) 0.0278(10) Uani 1 1 d . . . C6 C 0.8514(3) 0.2326(5) -0.2368(3) 0.0238(10) Uani 1 1 d . . . C7 C 0.7926(3) 0.1382(5) -0.2123(3) 0.0242(10) Uani 1 1 d . . . C8 C 0.6847(3) 0.1268(5) -0.1354(4) 0.0269(10) Uani 1 1 d . . . H8A H 0.7046 0.0347 -0.1103 0.032 Uiso 1 1 calc R . . H8B H 0.6415 0.1096 -0.1870 0.032 Uiso 1 1 calc R . . C9 C 0.6638(3) 0.2113(5) -0.0495(4) 0.0304(11) Uani 1 1 d . . . H9A H 0.7081 0.2436 -0.0049 0.036 Uiso 1 1 calc R . . H9B H 0.6365 0.2956 -0.0770 0.036 Uiso 1 1 calc R . . C10 C 0.6183(2) 0.1273(5) 0.0116(4) 0.0262(10) Uani 1 1 d . . . H10A H 0.5767 0.0861 -0.0340 0.031 Uiso 1 1 calc R . . H10B H 0.6475 0.0490 0.0454 0.031 Uiso 1 1 calc R . . C11 C 0.5907(3) 0.2163(5) 0.0897(4) 0.0285(11) Uani 1 1 d . . . H11A H 0.6321 0.2625 0.1324 0.034 Uiso 1 1 calc R . . H11B H 0.5589 0.2909 0.0555 0.034 Uiso 1 1 calc R . . C12 C 0.5493(3) 0.1317(5) 0.1553(4) 0.0310(11) Uani 1 1 d . . . H12A H 0.5834 0.0683 0.1980 0.037 Uiso 1 1 calc R . . H12B H 0.5135 0.0723 0.1120 0.037 Uiso 1 1 calc R . . C13 C 0.5104(2) 0.2204(5) 0.2218(4) 0.0251(10) Uani 1 1 d . . . C14 C 0.4380(3) 0.2246(5) 0.3525(4) 0.0280(10) Uani 1 1 d . . . H14A H 0.4014 0.2868 0.3132 0.034 Uiso 1 1 calc R . . H14B H 0.4724 0.2845 0.3975 0.034 Uiso 1 1 calc R . . C15 C 0.4007(3) 0.1255(5) 0.4155(4) 0.0308(11) Uani 1 1 d . . . H15A H 0.3647 0.0679 0.3711 0.037 Uiso 1 1 calc R . . H15B H 0.4367 0.0614 0.4538 0.037 Uiso 1 1 calc R . . C16 C 0.3635(3) 0.2084(5) 0.4871(4) 0.0263(10) Uani 1 1 d . . . H16A H 0.3259 0.2684 0.4477 0.032 Uiso 1 1 calc R . . H16B H 0.3993 0.2712 0.5273 0.032 Uiso 1 1 calc R . . C17 C 0.3288(3) 0.1176(5) 0.5578(4) 0.0292(11) Uani 1 1 d . . . H17A H 0.2939 0.0524 0.5184 0.035 Uiso 1 1 calc R . . H17B H 0.3663 0.0607 0.6001 0.035 Uiso 1 1 calc R . . C18 C 0.2901(3) 0.2078(5) 0.6242(4) 0.0280(10) Uani 1 1 d . . . H18A H 0.3242 0.2797 0.6572 0.034 Uiso 1 1 calc R . . H18B H 0.2500 0.2576 0.5814 0.034 Uiso 1 1 calc R . . C19 C 0.2600(2) 0.1274(5) 0.7043(4) 0.0250(10) Uani 1 1 d . . . C20 C 0.1854(2) 0.1702(5) 0.8365(3) 0.0255(10) Uani 1 1 d . . . C21 C 0.1963(3) 0.0428(5) 0.8872(3) 0.0257(10) Uani 1 1 d . . . H21 H 0.2275 -0.0260 0.8674 0.031 Uiso 1 1 calc R . . C22 C 0.1611(3) 0.0174(5) 0.9669(4) 0.0289(10) Uani 1 1 d . . . H22 H 0.1688 -0.0693 1.0017 0.035 Uiso 1 1 calc R . . C23 C 0.1150(3) 0.1158(6) 0.9967(4) 0.0367(12) Uani 1 1 d . . . H23 H 0.0908 0.0964 1.0508 0.044 Uiso 1 1 calc R . . C25 C 0.1402(3) 0.2700(6) 0.8679(4) 0.0331(11) Uani 1 1 d . . . H25 H 0.1337 0.3580 0.8347 0.040 Uiso 1 1 calc R . . C24 C 0.1049(3) 0.2432(6) 0.9463(4) 0.0382(13) Uani 1 1 d . . . H24 H 0.0736 0.3119 0.9660 0.046 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 0.060(2) 0.0301(16) 0.0263(15) -0.0076(12) 0.0192(14) -0.0112(14) F2 0.0456(18) 0.0383(17) 0.0357(17) 0.0034(13) 0.0257(14) 0.0031(13) F3 0.0329(16) 0.051(2) 0.054(2) 0.0035(16) 0.0148(15) -0.0113(14) F4 0.053(2) 0.055(2) 0.046(2) -0.0193(17) 0.0071(16) -0.0247(17) F5 0.0489(18) 0.0448(18) 0.0246(15) -0.0113(13) 0.0144(13) -0.0087(14) O1 0.046(2) 0.0212(17) 0.0350(19) -0.0004(14) 0.0185(16) 0.0001(15) O2 0.044(2) 0.0190(18) 0.046(2) -0.0007(15) 0.0212(17) -0.0010(15) O3 0.043(2) 0.0175(16) 0.041(2) 0.0017(14) 0.0179(16) 0.0015(14) N1 0.035(2) 0.0176(18) 0.030(2) -0.0001(16) 0.0142(17) -0.0029(16) N2 0.031(2) 0.0176(19) 0.043(2) -0.0014(17) 0.0173(18) 0.0015(16) N3 0.033(2) 0.0195(19) 0.031(2) 0.0044(16) 0.0110(17) 0.0042(16) C1 0.041(3) 0.021(2) 0.022(2) 0.0004(18) 0.009(2) 0.004(2) C2 0.032(2) 0.033(3) 0.024(2) 0.005(2) 0.0114(19) 0.009(2) C3 0.028(2) 0.033(3) 0.038(3) 0.006(2) 0.008(2) -0.001(2) C4 0.029(2) 0.038(3) 0.029(3) -0.006(2) 0.000(2) -0.003(2) C5 0.033(2) 0.029(2) 0.021(2) -0.0001(19) 0.0048(18) 0.002(2) C6 0.029(2) 0.022(2) 0.022(2) 0.0017(17) 0.0079(18) 0.0019(18) C7 0.032(2) 0.023(2) 0.018(2) 0.0005(17) 0.0047(18) 0.0007(18) C8 0.028(2) 0.022(2) 0.032(2) 0.0001(19) 0.0099(19) -0.0034(18) C9 0.035(3) 0.023(2) 0.035(3) -0.001(2) 0.012(2) -0.002(2) C10 0.023(2) 0.022(2) 0.034(3) -0.0004(19) 0.0073(19) -0.0005(18) C11 0.031(2) 0.022(2) 0.035(3) -0.0020(19) 0.011(2) -0.0039(19) C12 0.035(3) 0.021(2) 0.041(3) 0.000(2) 0.017(2) 0.0004(19) C13 0.022(2) 0.022(2) 0.033(3) 0.0005(19) 0.0063(18) -0.0004(17) C14 0.033(3) 0.020(2) 0.033(3) -0.0026(19) 0.012(2) 0.0016(19) C15 0.034(3) 0.021(2) 0.041(3) -0.001(2) 0.016(2) -0.0008(19) C16 0.026(2) 0.024(2) 0.029(2) -0.0005(19) 0.0063(19) 0.0027(19) C17 0.034(3) 0.023(2) 0.035(3) 0.0006(19) 0.015(2) 0.0018(19) C18 0.034(3) 0.022(2) 0.030(2) 0.0039(19) 0.011(2) 0.0020(19) C19 0.027(2) 0.020(2) 0.028(2) 0.0001(18) 0.0062(18) -0.0006(18) C20 0.024(2) 0.026(2) 0.027(2) -0.0015(19) 0.0048(18) -0.0016(18) C21 0.029(2) 0.022(2) 0.026(2) -0.0011(18) 0.0035(18) -0.0013(18) C22 0.029(2) 0.031(3) 0.025(2) 0.0051(19) 0.0013(18) -0.007(2) C23 0.038(3) 0.047(3) 0.027(3) 0.003(2) 0.009(2) -0.002(2) C25 0.033(3) 0.031(3) 0.037(3) 0.004(2) 0.012(2) 0.006(2) C24 0.035(3) 0.040(3) 0.043(3) 0.003(2) 0.016(2) 0.008(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag F1 C1 1.342(6) . ? F2 C2 1.339(5) . ? F3 C3 1.336(6) . ? F4 C4 1.347(6) . ? F5 C5 1.350(5) . ? O1 C7 1.229(6) . ? O2 C13 1.234(6) . ? O3 C19 1.229(6) . ? N1 C7 1.330(6) . ? N1 C8 1.473(6) . ? N1 H1 0.8800 . ? N2 C13 1.330(6) . ? N2 C14 1.454(6) . ? N2 H2 0.8800 . ? N3 C19 1.354(6) . ? N3 C20 1.422(6) . ? N3 H3 0.8800 . ? C1 C2 1.355(7) . ? C1 C6 1.402(6) . ? C2 C3 1.391(8) . ? C3 C4 1.381(7) . ? C4 C5 1.363(7) . ? C5 C6 1.384(7) . ? C6 C7 1.510(6) . ? C8 C9 1.527(7) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.522(6) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.520(7) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.516(7) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C13 1.519(7) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C14 C15 1.527(7) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 C16 1.518(6) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 C17 1.525(7) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 C18 1.522(6) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 C19 1.520(6) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C20 C21 1.391(7) . ? C20 C25 1.392(7) . ? C21 C22 1.388(7) . ? C21 H21 0.9500 . ? C22 C23 1.387(8) . ? C22 H22 0.9500 . ? C23 C24 1.389(8) . ? C23 H23 0.9500 . ? C25 C24 1.377(8) . ? C25 H25 0.9500 . ? C24 H24 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 C7 N1 C8 121.6(4) . . ? C7 N1 H1 119.2 . . ? C8 N1 H1 119.2 . . ? C13 N2 C14 121.1(4) . . ? C13 N2 H2 119.5 . . ? C14 N2 H2 119.5 . . ? C19 N3 C20 128.9(4) . . ? C19 N3 H3 115.5 . . ? C20 N3 H3 115.5 . . ? F1 C1 C2 118.0(4) . . ? F1 C1 C6 119.1(4) . . ? C2 C1 C6 122.8(5) . . ? F2 C2 C1 121.8(5) . . ? F2 C2 C3 118.5(5) . . ? C1 C2 C3 119.7(4) . . ? F3 C3 C4 120.3(5) . . ? F3 C3 C2 120.7(5) . . ? C4 C3 C2 119.0(5) . . ? F4 C4 C5 120.8(5) . . ? F4 C4 C3 119.0(5) . . ? C5 C4 C3 120.1(5) . . ? F5 C5 C4 117.5(4) . . ? F5 C5 C6 119.8(4) . . ? C4 C5 C6 122.7(4) . . ? C5 C6 C1 115.7(4) . . ? C5 C6 C7 123.3(4) . . ? C1 C6 C7 120.9(4) . . ? O1 C7 N1 124.6(4) . . ? O1 C7 C6 120.3(4) . . ? N1 C7 C6 115.0(4) . . ? N1 C8 C9 110.1(4) . . ? N1 C8 H8A 109.6 . . ? C9 C8 H8A 109.6 . . ? N1 C8 H8B 109.6 . . ? C9 C8 H8B 109.6 . . ? H8A C8 H8B 108.2 . . ? C10 C9 C8 112.8(4) . . ? C10 C9 H9A 109.0 . . ? C8 C9 H9A 109.0 . . ? C10 C9 H9B 109.0 . . ? C8 C9 H9B 109.0 . . ? H9A C9 H9B 107.8 . . ? C11 C10 C9 112.5(4) . . ? C11 C10 H10A 109.1 . . ? C9 C10 H10A 109.1 . . ? C11 C10 H10B 109.1 . . ? C9 C10 H10B 109.1 . . ? H10A C10 H10B 107.8 . . ? C12 C11 C10 112.9(4) . . ? C12 C11 H11A 109.0 . . ? C10 C11 H11A 109.0 . . ? C12 C11 H11B 109.0 . . ? C10 C11 H11B 109.0 . . ? H11A C11 H11B 107.8 . . ? C11 C12 C13 114.1(4) . . ? C11 C12 H12A 108.7 . . ? C13 C12 H12A 108.7 . . ? C11 C12 H12B 108.7 . . ? C13 C12 H12B 108.7 . . ? H12A C12 H12B 107.6 . . ? O2 C13 N2 121.4(4) . . ? O2 C13 C12 122.4(4) . . ? N2 C13 C12 116.2(4) . . ? N2 C14 C15 112.9(4) . . ? N2 C14 H14A 109.0 . . ? C15 C14 H14A 109.0 . . ? N2 C14 H14B 109.0 . . ? C15 C14 H14B 109.0 . . ? H14A C14 H14B 107.8 . . ? C16 C15 C14 110.5(4) . . ? C16 C15 H15A 109.6 . . ? C14 C15 H15A 109.6 . . ? C16 C15 H15B 109.6 . . ? C14 C15 H15B 109.6 . . ? H15A C15 H15B 108.1 . . ? C15 C16 C17 114.1(4) . . ? C15 C16 H16A 108.7 . . ? C17 C16 H16A 108.7 . . ? C15 C16 H16B 108.7 . . ? C17 C16 H16B 108.7 . . ? H16A C16 H16B 107.6 . . ? C18 C17 C16 111.0(4) . . ? C18 C17 H17A 109.4 . . ? C16 C17 H17A 109.4 . . ? C18 C17 H17B 109.4 . . ? C16 C17 H17B 109.4 . . ? H17A C17 H17B 108.0 . . ? C19 C18 C17 114.8(4) . . ? C19 C18 H18A 108.6 . . ? C17 C18 H18A 108.6 . . ? C19 C18 H18B 108.6 . . ? C17 C18 H18B 108.6 . . ? H18A C18 H18B 107.5 . . ? O3 C19 N3 123.9(4) . . ? O3 C19 C18 122.7(4) . . ? N3 C19 C18 113.4(4) . . ? C21 C20 C25 119.2(4) . . ? C21 C20 N3 123.8(4) . . ? C25 C20 N3 116.9(4) . . ? C22 C21 C20 119.2(4) . . ? C22 C21 H21 120.4 . . ? C20 C21 H21 120.4 . . ? C23 C22 C21 121.5(5) . . ? C23 C22 H22 119.3 . . ? C21 C22 H22 119.3 . . ? C22 C23 C24 118.9(5) . . ? C22 C23 H23 120.5 . . ? C24 C23 H23 120.5 . . ? C24 C25 C20 121.1(5) . . ? C24 C25 H25 119.4 . . ? C20 C25 H25 119.4 . . ? C25 C24 C23 120.0(5) . . ? C25 C24 H24 120.0 . . ? C23 C24 H24 120.0 . . ? 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 F1 C1 C2 F2 -0.6(7) . . . . ? C6 C1 C2 F2 -177.6(4) . . . . ? F1 C1 C2 C3 178.6(4) . . . . ? C6 C1 C2 C3 1.5(8) . . . . ? F2 C2 C3 F3 0.3(7) . . . . ? C1 C2 C3 F3 -178.9(5) . . . . ? F2 C2 C3 C4 177.7(5) . . . . ? C1 C2 C3 C4 -1.5(8) . . . . ? F3 C3 C4 F4 -3.1(8) . . . . ? C2 C3 C4 F4 179.5(5) . . . . ? F3 C3 C4 C5 178.2(5) . . . . ? C2 C3 C4 C5 0.7(8) . . . . ? F4 C4 C5 F5 0.1(7) . . . . ? C3 C4 C5 F5 178.8(5) . . . . ? F4 C4 C5 C6 -178.8(5) . . . . ? C3 C4 C5 C6 0.0(8) . . . . ? F5 C5 C6 C1 -178.8(4) . . . . ? C4 C5 C6 C1 0.0(7) . . . . ? F5 C5 C6 C7 -3.7(7) . . . . ? C4 C5 C6 C7 175.2(5) . . . . ? F1 C1 C6 C5 -177.8(4) . . . . ? C2 C1 C6 C5 -0.8(7) . . . . ? F1 C1 C6 C7 7.0(7) . . . . ? C2 C1 C6 C7 -176.0(4) . . . . ? C8 N1 C7 O1 8.8(7) . . . . ? C8 N1 C7 C6 -168.5(4) . . . . ? C5 C6 C7 O1 -129.8(5) . . . . ? C1 C6 C7 O1 45.1(7) . . . . ? C5 C6 C7 N1 47.6(6) . . . . ? C1 C6 C7 N1 -137.5(5) . . . . ? C7 N1 C8 C9 142.9(5) . . . . ? N1 C8 C9 C10 -169.8(4) . . . . ? C8 C9 C10 C11 -173.7(4) . . . . ? C9 C10 C11 C12 -176.3(4) . . . . ? C10 C11 C12 C13 -170.1(4) . . . . ? C14 N2 C13 O2 -1.4(7) . . . . ? C14 N2 C13 C12 179.4(4) . . . . ? C11 C12 C13 O2 4.2(7) . . . . ? C11 C12 C13 N2 -176.6(4) . . . . ? C13 N2 C14 C15 178.0(4) . . . . ? N2 C14 C15 C16 178.2(4) . . . . ? C14 C15 C16 C17 -176.3(4) . . . . ? C15 C16 C17 C18 -177.7(4) . . . . ? C16 C17 C18 C19 -174.3(4) . . . . ? C20 N3 C19 O3 -0.7(8) . . . . ? C20 N3 C19 C18 -178.0(4) . . . . ? C17 C18 C19 O3 8.9(7) . . . . ? C17 C18 C19 N3 -173.8(4) . . . . ? C19 N3 C20 C21 9.6(8) . . . . ? C19 N3 C20 C25 -172.7(5) . . . . ? C25 C20 C21 C22 0.9(7) . . . . ? N3 C20 C21 C22 178.5(4) . . . . ? C20 C21 C22 C23 0.4(7) . . . . ? C21 C22 C23 C24 -1.0(8) . . . . ? C21 C20 C25 C24 -1.7(8) . . . . ? N3 C20 C25 C24 -179.5(5) . . . . ? C20 C25 C24 C23 1.2(9) . . . . ? C22 C23 C24 C25 0.2(9) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.471 _refine_diff_density_min -0.410 _refine_diff_density_rms 0.110 _database_code_depnum_ccdc_archive 'CCDC 965770' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_cd212448 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H17 F5 N2 O2' _chemical_formula_weight 400.35 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' 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 8.7960(9) _cell_length_b 20.174(2) _cell_length_c 10.7947(12) _cell_angle_alpha 90.00 _cell_angle_beta 105.704(3) _cell_angle_gamma 90.00 _cell_volume 1844.0(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1803 _cell_measurement_theta_min 5.628 _cell_measurement_theta_max 46.168 _exptl_crystal_description prismatic _exptl_crystal_colour colorless _exptl_crystal_size_max 0.256 _exptl_crystal_size_mid 0.211 _exptl_crystal_size_min 0.145 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.442 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 824 _exptl_absorpt_coefficient_mu 0.128 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.0890 _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 11065 _diffrn_reflns_av_R_equivalents 0.0414 _diffrn_reflns_av_sigmaI/netI 0.0471 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.02 _diffrn_reflns_theta_max 26.00 _reflns_number_total 3616 _reflns_number_gt 2174 _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^)+(0.0636P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3616 _refine_ls_number_parameters 261 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0858 _refine_ls_R_factor_gt 0.0463 _refine_ls_wR_factor_ref 0.1318 _refine_ls_wR_factor_gt 0.1133 _refine_ls_goodness_of_fit_ref 1.013 _refine_ls_restrained_S_all 1.013 _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 0.27844(17) 0.69977(6) 0.36893(12) 0.0788(4) Uani 1 1 d . . . F2 F 0.2941(2) 0.56722(7) 0.38322(16) 0.1048(6) Uani 1 1 d . . . F3 F 0.44421(17) 0.49850(6) 0.23741(14) 0.0945(5) Uani 1 1 d . . . F4 F 0.57973(17) 0.56329(6) 0.07504(15) 0.0867(4) Uani 1 1 d . . . F5 F 0.56077(17) 0.69531(6) 0.05676(13) 0.0817(4) Uani 1 1 d . . . N1 N 0.2747(2) 0.80413(8) 0.17222(16) 0.0489(4) Uani 1 1 d . . . N2 N -0.1797(2) 0.76314(8) 0.41696(19) 0.0543(5) Uani 1 1 d . . . O1 O 0.54034(17) 0.80780(7) 0.23186(14) 0.0636(4) Uani 1 1 d . . . O2 O 0.01943(18) 0.78501(7) 0.59188(15) 0.0688(4) Uani 1 1 d . . . C1 C 0.3506(2) 0.66718(11) 0.29272(19) 0.0547(5) Uani 1 1 d . . . C2 C 0.3591(3) 0.59975(11) 0.3018(2) 0.0634(6) Uani 1 1 d . . . C3 C 0.4357(3) 0.56441(10) 0.2285(2) 0.0615(6) Uani 1 1 d . . . C4 C 0.5036(2) 0.59745(10) 0.1465(2) 0.0584(5) Uani 1 1 d . . . C5 C 0.4941(2) 0.66474(10) 0.1393(2) 0.0535(5) Uani 1 1 d . . . C6 C 0.4178(2) 0.70221(9) 0.21123(17) 0.0457(5) Uani 1 1 d . . . C7 C 0.4156(2) 0.77651(10) 0.20544(17) 0.0463(5) Uani 1 1 d . . . C8 C 0.2509(3) 0.87527(9) 0.1692(2) 0.0560(5) Uani 1 1 d . . . H8A H 0.1589 0.8861 0.0994 0.067 Uiso 1 1 calc R . . H8B H 0.3416 0.8968 0.1519 0.067 Uiso 1 1 calc R . . C9 C 0.2281(3) 0.90195(10) 0.2934(2) 0.0591(6) Uani 1 1 d . . . H9A H 0.2189 0.9498 0.2874 0.071 Uiso 1 1 calc R . . H9B H 0.3207 0.8915 0.3630 0.071 Uiso 1 1 calc R . . C10 C 0.0836(3) 0.87403(11) 0.3249(2) 0.0642(6) Uani 1 1 d . . . H10A H 0.0990 0.8268 0.3407 0.077 Uiso 1 1 calc R . . H10B H -0.0065 0.8795 0.2505 0.077 Uiso 1 1 calc R . . C11 C 0.0451(3) 0.90550(10) 0.4403(2) 0.0653(6) Uani 1 1 d . . . H11A H 0.0314 0.9528 0.4258 0.078 Uiso 1 1 calc R . . H11B H 0.1333 0.8989 0.5157 0.078 Uiso 1 1 calc R . . C12 C -0.1033(3) 0.87694(10) 0.4659(2) 0.0615(6) Uani 1 1 d . . . H12A H -0.1262 0.9004 0.5372 0.074 Uiso 1 1 calc R . . H12B H -0.1918 0.8832 0.3906 0.074 Uiso 1 1 calc R . . C13 C -0.0837(2) 0.80437(10) 0.4973(2) 0.0508(5) Uani 1 1 d . . . C14 C -0.1762(2) 0.69274(9) 0.42992(18) 0.0488(5) Uani 1 1 d . . . C15 C -0.2496(3) 0.66225(10) 0.5120(2) 0.0596(6) Uani 1 1 d . . . H15 H -0.2984 0.6878 0.5619 0.072 Uiso 1 1 calc R . . C16 C -0.2514(3) 0.59428(11) 0.5209(2) 0.0698(6) Uani 1 1 d . . . H16 H -0.3015 0.5741 0.5765 0.084 Uiso 1 1 calc R . . C17 C -0.1801(3) 0.55651(11) 0.4487(2) 0.0691(6) Uani 1 1 d . . . H17 H -0.1811 0.5105 0.4550 0.083 Uiso 1 1 calc R . . C18 C -0.1070(3) 0.58631(12) 0.3668(2) 0.0720(7) Uani 1 1 d . . . H18 H -0.0584 0.5603 0.3174 0.086 Uiso 1 1 calc R . . C19 C -0.1042(3) 0.65465(11) 0.3564(2) 0.0621(6) Uani 1 1 d . . . H19 H -0.0543 0.6746 0.3003 0.075 Uiso 1 1 calc R . . H1 H 0.195(2) 0.7805(9) 0.1517(15) 0.033(5) Uiso 1 1 d . . . H2 H -0.250(3) 0.7784(11) 0.357(2) 0.060(7) Uiso 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 F1 0.1034(11) 0.0713(9) 0.0795(9) 0.0111(7) 0.0551(8) 0.0112(7) F2 0.1457(14) 0.0723(10) 0.1224(12) 0.0364(8) 0.0810(11) 0.0047(9) F3 0.1078(11) 0.0467(9) 0.1337(13) 0.0145(8) 0.0406(10) 0.0086(7) F4 0.0931(10) 0.0658(9) 0.1150(11) -0.0150(7) 0.0519(9) 0.0096(7) F5 0.1028(11) 0.0650(9) 0.0996(10) 0.0012(7) 0.0657(9) -0.0071(7) N1 0.0433(10) 0.0424(10) 0.0581(11) 0.0011(8) 0.0086(8) -0.0033(8) N2 0.0474(10) 0.0481(11) 0.0613(11) 0.0083(9) 0.0044(9) 0.0039(9) O1 0.0497(9) 0.0547(9) 0.0811(10) 0.0078(7) 0.0087(7) -0.0066(7) O2 0.0632(10) 0.0596(10) 0.0727(10) -0.0025(8) -0.0004(8) 0.0067(7) C1 0.0553(13) 0.0576(14) 0.0536(12) 0.0061(10) 0.0185(10) 0.0052(10) C2 0.0693(15) 0.0532(15) 0.0716(14) 0.0201(11) 0.0257(12) 0.0007(11) C3 0.0614(14) 0.0401(13) 0.0805(16) 0.0110(11) 0.0149(12) 0.0049(10) C4 0.0496(12) 0.0527(14) 0.0728(14) -0.0043(11) 0.0166(11) 0.0047(10) C5 0.0507(12) 0.0515(13) 0.0617(13) 0.0052(10) 0.0208(10) -0.0047(9) C6 0.0410(11) 0.0459(12) 0.0476(11) 0.0034(9) 0.0076(9) 0.0004(8) C7 0.0466(13) 0.0486(12) 0.0427(11) 0.0032(8) 0.0107(9) -0.0041(9) C8 0.0607(13) 0.0445(13) 0.0620(13) 0.0083(10) 0.0148(10) 0.0031(9) C9 0.0666(14) 0.0407(12) 0.0689(14) 0.0017(10) 0.0164(11) -0.0013(10) C10 0.0654(15) 0.0520(14) 0.0761(15) -0.0053(11) 0.0209(12) -0.0021(10) C11 0.0716(15) 0.0461(13) 0.0812(16) -0.0072(11) 0.0257(12) -0.0006(11) C12 0.0598(14) 0.0463(13) 0.0819(16) -0.0043(10) 0.0253(12) 0.0074(10) C13 0.0422(11) 0.0501(13) 0.0615(13) -0.0016(10) 0.0166(11) 0.0066(10) C14 0.0417(11) 0.0448(12) 0.0550(12) 0.0037(9) 0.0049(9) 0.0028(9) C15 0.0620(14) 0.0557(14) 0.0652(14) 0.0027(11) 0.0240(11) 0.0030(10) C16 0.0755(16) 0.0583(16) 0.0747(16) 0.0107(12) 0.0189(13) -0.0061(12) C17 0.0715(15) 0.0469(14) 0.0792(16) -0.0019(12) 0.0041(13) -0.0033(11) C18 0.0722(16) 0.0601(16) 0.0813(17) -0.0182(13) 0.0164(13) 0.0065(12) C19 0.0591(14) 0.0613(15) 0.0676(14) -0.0007(11) 0.0198(11) -0.0010(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 C1 1.340(2) . ? F2 C2 1.342(2) . ? F3 C3 1.334(2) . ? F4 C4 1.341(2) . ? F5 C5 1.342(2) . ? N1 C7 1.317(2) . ? N1 C8 1.449(2) . ? N1 H1 0.827(17) . ? N2 C13 1.327(3) . ? N2 C14 1.427(2) . ? N2 H2 0.82(2) . ? O1 C7 1.230(2) . ? O2 C13 1.231(2) . ? C1 C2 1.364(3) . ? C1 C6 1.380(3) . ? C2 C3 1.371(3) . ? C3 C4 1.367(3) . ? C4 C5 1.361(3) . ? C5 C6 1.381(3) . ? C6 C7 1.500(3) . ? C8 C9 1.507(3) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.512(3) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C11 1.515(3) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.519(3) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C13 1.502(3) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C14 C15 1.375(3) . ? C14 C19 1.376(3) . ? C15 C16 1.375(3) . ? C15 H15 0.9300 . ? C16 C17 1.359(3) . ? C16 H16 0.9300 . ? C17 C18 1.365(3) . ? C17 H17 0.9300 . ? C18 C19 1.384(3) . ? C18 H18 0.9300 . ? C19 H19 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 C7 N1 C8 122.98(18) . . ? C7 N1 H1 119.7(12) . . ? C8 N1 H1 117.3(12) . . ? C13 N2 C14 124.53(19) . . ? C13 N2 H2 119.2(15) . . ? C14 N2 H2 116.1(15) . . ? F1 C1 C2 118.10(19) . . ? F1 C1 C6 119.73(19) . . ? C2 C1 C6 122.1(2) . . ? F2 C2 C1 120.7(2) . . ? F2 C2 C3 119.1(2) . . ? C1 C2 C3 120.2(2) . . ? F3 C3 C4 120.5(2) . . ? F3 C3 C2 120.2(2) . . ? C4 C3 C2 119.3(2) . . ? F4 C4 C5 120.8(2) . . ? F4 C4 C3 119.7(2) . . ? C5 C4 C3 119.5(2) . . ? F5 C5 C4 117.74(19) . . ? F5 C5 C6 119.20(18) . . ? C4 C5 C6 123.06(19) . . ? C1 C6 C5 115.80(19) . . ? C1 C6 C7 122.37(18) . . ? C5 C6 C7 121.75(17) . . ? O1 C7 N1 124.09(19) . . ? O1 C7 C6 120.16(18) . . ? N1 C7 C6 115.75(17) . . ? N1 C8 C9 112.76(16) . . ? N1 C8 H8A 109.0 . . ? C9 C8 H8A 109.0 . . ? N1 C8 H8B 109.0 . . ? C9 C8 H8B 109.0 . . ? H8A C8 H8B 107.8 . . ? C8 C9 C10 112.95(18) . . ? C8 C9 H9A 109.0 . . ? C10 C9 H9A 109.0 . . ? C8 C9 H9B 109.0 . . ? C10 C9 H9B 109.0 . . ? H9A C9 H9B 107.8 . . ? C9 C10 C11 114.68(18) . . ? C9 C10 H10A 108.6 . . ? C11 C10 H10A 108.6 . . ? C9 C10 H10B 108.6 . . ? C11 C10 H10B 108.6 . . ? H10A C10 H10B 107.6 . . ? C10 C11 C12 112.62(18) . . ? C10 C11 H11A 109.1 . . ? C12 C11 H11A 109.1 . . ? C10 C11 H11B 109.1 . . ? C12 C11 H11B 109.1 . . ? H11A C11 H11B 107.8 . . ? C13 C12 C11 111.03(17) . . ? C13 C12 H12A 109.4 . . ? C11 C12 H12A 109.4 . . ? C13 C12 H12B 109.4 . . ? C11 C12 H12B 109.4 . . ? H12A C12 H12B 108.0 . . ? O2 C13 N2 122.60(19) . . ? O2 C13 C12 120.67(19) . . ? N2 C13 C12 116.71(19) . . ? C15 C14 C19 119.4(2) . . ? C15 C14 N2 120.48(18) . . ? C19 C14 N2 120.03(18) . . ? C14 C15 C16 120.5(2) . . ? C14 C15 H15 119.7 . . ? C16 C15 H15 119.7 . . ? C17 C16 C15 120.2(2) . . ? C17 C16 H16 119.9 . . ? C15 C16 H16 119.9 . . ? C16 C17 C18 119.7(2) . . ? C16 C17 H17 120.1 . . ? C18 C17 H17 120.1 . . ? C17 C18 C19 120.9(2) . . ? C17 C18 H18 119.6 . . ? C19 C18 H18 119.6 . . ? C14 C19 C18 119.2(2) . . ? C14 C19 H19 120.4 . . ? C18 C19 H19 120.4 . . ? 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 F1 C1 C2 F2 1.3(3) . . . . ? C6 C1 C2 F2 179.18(19) . . . . ? F1 C1 C2 C3 -178.13(19) . . . . ? C6 C1 C2 C3 -0.2(3) . . . . ? F2 C2 C3 F3 0.5(3) . . . . ? C1 C2 C3 F3 179.94(19) . . . . ? F2 C2 C3 C4 -179.3(2) . . . . ? C1 C2 C3 C4 0.2(3) . . . . ? F3 C3 C4 F4 -0.3(3) . . . . ? C2 C3 C4 F4 179.54(19) . . . . ? F3 C3 C4 C5 -179.71(19) . . . . ? C2 C3 C4 C5 0.1(3) . . . . ? F4 C4 C5 F5 1.2(3) . . . . ? C3 C4 C5 F5 -179.30(18) . . . . ? F4 C4 C5 C6 -179.71(18) . . . . ? C3 C4 C5 C6 -0.3(3) . . . . ? F1 C1 C6 C5 177.94(17) . . . . ? C2 C1 C6 C5 0.1(3) . . . . ? F1 C1 C6 C7 0.9(3) . . . . ? C2 C1 C6 C7 -176.97(19) . . . . ? F5 C5 C6 C1 179.21(17) . . . . ? C4 C5 C6 C1 0.2(3) . . . . ? F5 C5 C6 C7 -3.7(3) . . . . ? C4 C5 C6 C7 177.23(19) . . . . ? C8 N1 C7 O1 -3.1(3) . . . . ? C8 N1 C7 C6 176.26(17) . . . . ? C1 C6 C7 O1 119.1(2) . . . . ? C5 C6 C7 O1 -57.8(3) . . . . ? C1 C6 C7 N1 -60.3(2) . . . . ? C5 C6 C7 N1 122.8(2) . . . . ? C7 N1 C8 C9 -93.0(2) . . . . ? N1 C8 C9 C10 -61.9(2) . . . . ? C8 C9 C10 C11 -173.04(18) . . . . ? C9 C10 C11 C12 178.56(19) . . . . ? C10 C11 C12 C13 62.4(3) . . . . ? C14 N2 C13 O2 0.2(3) . . . . ? C14 N2 C13 C12 178.71(17) . . . . ? C11 C12 C13 O2 61.1(3) . . . . ? C11 C12 C13 N2 -117.4(2) . . . . ? C13 N2 C14 C15 81.8(3) . . . . ? C13 N2 C14 C19 -100.7(2) . . . . ? C19 C14 C15 C16 0.0(3) . . . . ? N2 C14 C15 C16 177.5(2) . . . . ? C14 C15 C16 C17 0.2(3) . . . . ? C15 C16 C17 C18 -0.2(4) . . . . ? C16 C17 C18 C19 0.1(4) . . . . ? C15 C14 C19 C18 -0.1(3) . . . . ? N2 C14 C19 C18 -177.7(2) . . . . ? C17 C18 C19 C14 0.1(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2 O1 0.82(2) 2.06(2) 2.864(2) 167(2) 1_455 N1 H1 O2 0.827(17) 2.002(18) 2.824(2) 172.3(17) 4_575 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.219 _refine_diff_density_min -0.149 _refine_diff_density_rms 0.038 _database_code_depnum_ccdc_archive 'CCDC 965771' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_cd212256 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H11 F5 N2 O2' _chemical_formula_weight 358.27 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' 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 6.235(4) _cell_length_b 7.257(5) _cell_length_c 32.88(2) _cell_angle_alpha 87.826(13) _cell_angle_beta 89.408(12) _cell_angle_gamma 84.552(13) _cell_volume 1480.1(17) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3423 _cell_measurement_theta_min 4.959 _cell_measurement_theta_max 55.694 _exptl_crystal_description prismatic _exptl_crystal_colour colorless _exptl_crystal_size_max 0.321 _exptl_crystal_size_mid 0.212 _exptl_crystal_size_min 0.121 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.608 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 728 _exptl_absorpt_coefficient_mu 0.149 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.71726 _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 7991 _diffrn_reflns_av_R_equivalents 0.0452 _diffrn_reflns_av_sigmaI/netI 0.0821 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 39 _diffrn_reflns_theta_min 0.62 _diffrn_reflns_theta_max 25.50 _reflns_number_total 5441 _reflns_number_gt 4273 _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^)+(0.1233P)^2^+0.8691P] 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 5441 _refine_ls_number_parameters 452 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0885 _refine_ls_R_factor_gt 0.0749 _refine_ls_wR_factor_ref 0.2331 _refine_ls_wR_factor_gt 0.2220 _refine_ls_goodness_of_fit_ref 1.082 _refine_ls_restrained_S_all 1.084 _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 0.9092(4) 0.5974(4) 0.18116(8) 0.0596(7) Uani 1 1 d . . . F2 F 1.1884(4) 0.4961(4) 0.12299(10) 0.0630(8) Uani 1 1 d . . . F3 F 1.0820(5) 0.5535(5) 0.04379(9) 0.0670(8) Uani 1 1 d . . . F4 F 0.6808(5) 0.6968(5) 0.02396(8) 0.0667(8) Uani 1 1 d . . . F5 F 0.3924(4) 0.7872(4) 0.08113(8) 0.0546(7) Uani 1 1 d . . . F6 F -0.0985(4) 0.3134(4) 0.41792(8) 0.0516(7) Uani 1 1 d . . . F7 F 0.1830(5) 0.2078(5) 0.47554(8) 0.0649(8) Uani 1 1 d . . . F8 F 0.5857(5) 0.0685(5) 0.45637(9) 0.0675(8) Uani 1 1 d . . . F9 F 0.7032(4) 0.0336(4) 0.37770(9) 0.0617(8) Uani 1 1 d . . . F10 F 0.4304(4) 0.1484(4) 0.31905(8) 0.0601(7) Uani 1 1 d . . . N1 N 0.4670(7) 0.6220(6) 0.19654(11) 0.0575(11) Uani 1 1 d . . . H1 H 0.5448 0.5185 0.1943 0.069 Uiso 1 1 calc R . . N2 N 0.4377(6) 0.6473(5) 0.34010(10) 0.0457(9) Uani 1 1 d . . . H2 H 0.5573 0.5800 0.3368 0.055 Uiso 1 1 calc R . . N3 N -0.0029(7) 0.1867(6) 0.30197(11) 0.0528(10) Uani 1 1 d . . . H3 H 0.0779 0.0839 0.3030 0.063 Uiso 1 1 calc R . . N4 N -0.0769(6) 0.1022(5) 0.16011(11) 0.0464(9) Uani 1 1 d . . . H4 H 0.0434 0.0352 0.1635 0.056 Uiso 1 1 calc R . . O1 O 0.3614(6) 0.8941(5) 0.16404(12) 0.0620(9) Uani 1 1 d . . . O2 O 0.1689(6) 0.8112(5) 0.30510(9) 0.0573(9) Uani 1 1 d . . . O3 O -0.1257(5) 0.4404(4) 0.33506(10) 0.0542(8) Uani 1 1 d . . . O4 O -0.3492(6) 0.2529(5) 0.19452(10) 0.0624(10) Uani 1 1 d . . . C1 C 0.4723(7) 0.7462(6) 0.16647(13) 0.0437(10) Uani 1 1 d . . . C2 C 0.6373(7) 0.6951(6) 0.13375(12) 0.0392(9) Uani 1 1 d . . . C3 C 0.8445(7) 0.6215(6) 0.14295(13) 0.0406(9) Uani 1 1 d . . . C4 C 0.9935(7) 0.5722(6) 0.11292(14) 0.0440(10) Uani 1 1 d . . . C5 C 0.9378(7) 0.5995(6) 0.07302(13) 0.0453(10) Uani 1 1 d . . . C6 C 0.7366(7) 0.6727(6) 0.06286(12) 0.0439(10) Uani 1 1 d . . . C7 C 0.5875(7) 0.7211(6) 0.09312(13) 0.0409(9) Uani 1 1 d . . . C8 C 0.3397(9) 0.6476(10) 0.23312(15) 0.0691(16) Uani 1 1 d D . . H8A H 0.2690 0.5364 0.2395 0.083 Uiso 1 1 calc R . . H8B H 0.2288 0.7491 0.2285 0.083 Uiso 1 1 calc R . . C9 C 0.4711(9) 0.6873(10) 0.26767(15) 0.0704(16) Uani 1 1 d D . . H9A H 0.5455 0.7959 0.2608 0.084 Uiso 1 1 calc R . . H9B H 0.5793 0.5839 0.2726 0.084 Uiso 1 1 calc R . . C10 C 0.3431(8) 0.7203(7) 0.30581(13) 0.0481(11) Uani 1 1 d . . . C11 C 0.3664(7) 0.6666(5) 0.38083(12) 0.0375(9) Uani 1 1 d . . . C12 C 0.1552(7) 0.7214(6) 0.39151(13) 0.0426(10) Uani 1 1 d . . . H12 H 0.0508 0.7476 0.3716 0.051 Uiso 1 1 calc R . . C13 C 0.1027(8) 0.7365(7) 0.43183(14) 0.0509(11) Uani 1 1 d . . . H13 H -0.0389 0.7745 0.4390 0.061 Uiso 1 1 calc R . . C14 C 0.2523(8) 0.6972(7) 0.46199(14) 0.0530(12) Uani 1 1 d . . . H14 H 0.2135 0.7083 0.4892 0.064 Uiso 1 1 calc R . . C15 C 0.4609(8) 0.6411(7) 0.45096(14) 0.0542(12) Uani 1 1 d . . . H15 H 0.5641 0.6122 0.4710 0.065 Uiso 1 1 calc R . . C16 C 0.5194(8) 0.6271(6) 0.41026(13) 0.0454(10) Uani 1 1 d . . . H16 H 0.6614 0.5912 0.4030 0.055 Uiso 1 1 calc R . . C17 C -0.0064(7) 0.2947(6) 0.33285(12) 0.0405(9) Uani 1 1 d . . . C18 C 0.1522(6) 0.2346(5) 0.36595(12) 0.0357(9) Uani 1 1 d . . . C19 C 0.0985(7) 0.2491(5) 0.40656(12) 0.0380(9) Uani 1 1 d . . . C20 C 0.2437(7) 0.1935(6) 0.43715(12) 0.0427(10) Uani 1 1 d . . . C21 C 0.4475(7) 0.1223(6) 0.42752(14) 0.0457(10) Uani 1 1 d . . . C22 C 0.5055(7) 0.1057(6) 0.38746(14) 0.0427(10) Uani 1 1 d . . . C23 C 0.3599(7) 0.1619(6) 0.35765(13) 0.0416(9) Uani 1 1 d . . . C24 C -0.1300(8) 0.2342(7) 0.26620(13) 0.0538(12) Uani 1 1 d . . . H24A H -0.1245 0.3645 0.2589 0.065 Uiso 1 1 calc R . . H24B H -0.2790 0.2133 0.2718 0.065 Uiso 1 1 calc R . . C25 C -0.0476(9) 0.1210(8) 0.23209(14) 0.0603(14) Uani 1 1 d . . . H25A H -0.0531 -0.0090 0.2397 0.072 Uiso 1 1 calc R . . H25B H 0.1019 0.1415 0.2269 0.072 Uiso 1 1 calc R . . C26 C -0.1741(8) 0.1654(6) 0.19379(13) 0.0471(11) Uani 1 1 d . . . C27 C -0.1479(7) 0.1321(5) 0.11965(12) 0.0382(9) Uani 1 1 d . . . C28 C -0.3557(7) 0.1903(6) 0.10875(13) 0.0463(10) Uani 1 1 d . . . H28 H -0.4611 0.2132 0.1286 0.056 Uiso 1 1 calc R . . C29 C -0.4068(8) 0.2147(7) 0.06824(14) 0.0506(11) Uani 1 1 d . . . H29 H -0.5479 0.2533 0.0608 0.061 Uiso 1 1 calc R . . C30 C -0.2517(8) 0.1828(7) 0.03841(14) 0.0555(12) Uani 1 1 d . . . H30 H -0.2872 0.2003 0.0110 0.067 Uiso 1 1 calc R . . C31 C -0.0463(9) 0.1253(7) 0.04967(14) 0.0542(12) Uani 1 1 d . . . H31 H 0.0591 0.1039 0.0297 0.065 Uiso 1 1 calc R . . C32 C 0.0079(8) 0.0985(6) 0.08951(13) 0.0452(10) Uani 1 1 d . . . H32 H 0.1489 0.0578 0.0966 0.054 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 0.0481(15) 0.087(2) 0.0423(14) 0.0029(13) -0.0125(11) 0.0010(14) F2 0.0345(14) 0.075(2) 0.077(2) 0.0012(15) -0.0038(13) 0.0064(13) F3 0.0579(18) 0.085(2) 0.0576(17) -0.0076(15) 0.0192(14) -0.0049(15) F4 0.073(2) 0.088(2) 0.0375(14) 0.0016(14) -0.0053(13) -0.0027(17) F5 0.0454(15) 0.0655(17) 0.0504(15) -0.0007(12) -0.0113(11) 0.0090(12) F6 0.0439(14) 0.0614(16) 0.0477(14) -0.0095(12) 0.0049(11) 0.0072(12) F7 0.0701(19) 0.089(2) 0.0350(14) -0.0009(13) -0.0018(12) -0.0029(16) F8 0.0588(18) 0.080(2) 0.0625(18) 0.0041(15) -0.0248(14) -0.0015(15) F9 0.0350(14) 0.0708(19) 0.078(2) -0.0093(15) -0.0007(13) 0.0060(13) F10 0.0488(15) 0.086(2) 0.0447(15) -0.0107(14) 0.0111(12) 0.0016(14) N1 0.055(2) 0.076(3) 0.036(2) -0.0009(19) 0.0035(17) 0.023(2) N2 0.044(2) 0.055(2) 0.0354(18) -0.0029(16) -0.0014(15) 0.0130(16) N3 0.061(2) 0.055(2) 0.038(2) -0.0071(17) -0.0065(16) 0.0241(19) N4 0.048(2) 0.050(2) 0.0365(19) -0.0022(16) -0.0073(15) 0.0151(17) O1 0.056(2) 0.0493(19) 0.077(2) -0.0075(17) 0.0067(17) 0.0149(16) O2 0.060(2) 0.066(2) 0.0394(17) 0.0024(15) -0.0013(14) 0.0248(17) O3 0.061(2) 0.0489(18) 0.0493(18) -0.0078(14) -0.0096(15) 0.0166(15) O4 0.057(2) 0.074(2) 0.0502(19) -0.0072(17) -0.0040(15) 0.0286(18) C1 0.035(2) 0.050(3) 0.045(2) -0.007(2) -0.0052(17) 0.0062(19) C2 0.041(2) 0.035(2) 0.041(2) -0.0038(17) -0.0030(17) 0.0021(17) C3 0.041(2) 0.042(2) 0.038(2) 0.0008(17) -0.0059(17) -0.0022(18) C4 0.037(2) 0.040(2) 0.054(3) 0.0034(19) -0.0020(19) -0.0034(18) C5 0.043(2) 0.049(3) 0.044(2) -0.0028(19) 0.0101(18) -0.0026(19) C6 0.052(3) 0.046(2) 0.035(2) -0.0017(18) -0.0005(18) -0.009(2) C7 0.041(2) 0.037(2) 0.042(2) 0.0008(17) -0.0052(18) 0.0033(17) C8 0.054(3) 0.107(5) 0.042(3) -0.004(3) 0.003(2) 0.015(3) C9 0.050(3) 0.114(5) 0.044(3) -0.009(3) -0.002(2) 0.011(3) C10 0.052(3) 0.054(3) 0.035(2) -0.0045(19) -0.0029(18) 0.014(2) C11 0.045(2) 0.030(2) 0.037(2) -0.0014(16) -0.0054(17) 0.0000(17) C12 0.041(2) 0.049(2) 0.037(2) 0.0010(18) -0.0011(17) -0.0006(18) C13 0.050(3) 0.056(3) 0.047(3) -0.006(2) 0.003(2) -0.007(2) C14 0.063(3) 0.062(3) 0.035(2) -0.002(2) 0.003(2) -0.008(2) C15 0.060(3) 0.058(3) 0.044(3) 0.003(2) -0.013(2) -0.005(2) C16 0.045(2) 0.047(2) 0.041(2) 0.0057(19) -0.0017(18) 0.0077(19) C17 0.040(2) 0.045(2) 0.034(2) -0.0034(17) 0.0020(16) 0.0066(18) C18 0.037(2) 0.0311(19) 0.038(2) 0.0005(15) -0.0004(16) 0.0003(16) C19 0.039(2) 0.036(2) 0.038(2) -0.0025(16) 0.0042(16) -0.0002(17) C20 0.046(2) 0.046(2) 0.037(2) -0.0031(18) -0.0003(18) -0.0072(19) C21 0.043(2) 0.045(2) 0.050(3) 0.0033(19) -0.0118(19) -0.0102(19) C22 0.032(2) 0.041(2) 0.055(3) -0.0028(19) -0.0019(18) -0.0019(17) C23 0.041(2) 0.043(2) 0.041(2) -0.0051(18) 0.0052(18) -0.0035(18) C24 0.051(3) 0.068(3) 0.038(2) -0.006(2) -0.0083(19) 0.019(2) C25 0.070(3) 0.068(3) 0.038(2) -0.007(2) -0.010(2) 0.029(3) C26 0.055(3) 0.044(2) 0.039(2) -0.0019(18) -0.0059(19) 0.014(2) C27 0.046(2) 0.034(2) 0.035(2) 0.0001(16) -0.0031(17) -0.0015(17) C28 0.046(2) 0.049(3) 0.042(2) 0.0017(19) -0.0008(19) 0.001(2) C29 0.047(3) 0.057(3) 0.047(3) 0.008(2) -0.010(2) -0.006(2) C30 0.064(3) 0.064(3) 0.038(2) 0.001(2) -0.008(2) -0.005(2) C31 0.065(3) 0.063(3) 0.034(2) -0.005(2) 0.006(2) -0.003(2) C32 0.047(2) 0.049(2) 0.038(2) -0.0035(18) -0.0001(18) 0.0040(19) _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 C3 1.324(5) . ? F2 C4 1.326(5) . ? F3 C5 1.339(5) . ? F4 C6 1.330(5) . ? F5 C7 1.323(5) . ? F6 C19 1.327(5) . ? F7 C20 1.319(5) . ? F8 C21 1.311(5) . ? F9 C22 1.333(5) . ? F10 C23 1.343(5) . ? N1 C1 1.315(6) . ? N1 C8 1.443(6) . ? N1 H1 0.8600 . ? N2 C10 1.345(5) . ? N2 C11 1.414(5) . ? N2 H2 0.8600 . ? N3 C17 1.305(6) . ? N3 C24 1.438(5) . ? N3 H3 0.8600 . ? N4 C26 1.333(6) . ? N4 C27 1.409(5) . ? N4 H4 0.8600 . ? O1 C1 1.221(5) . ? O2 C10 1.216(5) . ? O3 C17 1.238(5) . ? O4 C26 1.210(5) . ? C1 C2 1.513(6) . ? C2 C7 1.377(6) . ? C2 C3 1.382(6) . ? C3 C4 1.382(6) . ? C4 C5 1.363(6) . ? C5 C6 1.355(7) . ? C6 C7 1.387(6) . ? C8 C9 1.461(7) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.494(7) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C11 C16 1.369(6) . ? C11 C12 1.385(6) . ? C12 C13 1.368(6) . ? C12 H12 0.9300 . ? C13 C14 1.372(7) . ? C13 H13 0.9300 . ? C14 C15 1.375(7) . ? C14 H14 0.9300 . ? C15 C16 1.388(7) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? C17 C18 1.502(6) . ? C18 C19 1.379(6) . ? C18 C23 1.380(6) . ? C19 C20 1.383(6) . ? C20 C21 1.365(7) . ? C21 C22 1.369(7) . ? C22 C23 1.367(6) . ? C24 C25 1.475(6) . ? C24 H24A 0.9700 . ? C24 H24B 0.9700 . ? C25 C26 1.501(6) . ? C25 H25A 0.9700 . ? C25 H25B 0.9700 . ? C27 C28 1.371(6) . ? C27 C32 1.392(6) . ? C28 C29 1.374(6) . ? C28 H28 0.9300 . ? C29 C30 1.381(7) . ? C29 H29 0.9300 . ? C30 C31 1.359(7) . ? C30 H30 0.9300 . ? C31 C32 1.359(6) . ? C31 H31 0.9300 . ? C32 H32 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 C8 124.5(4) . . ? C1 N1 H1 117.8 . . ? C8 N1 H1 117.8 . . ? C10 N2 C11 128.6(4) . . ? C10 N2 H2 115.7 . . ? C11 N2 H2 115.7 . . ? C17 N3 C24 122.1(4) . . ? C17 N3 H3 119.0 . . ? C24 N3 H3 119.0 . . ? C26 N4 C27 127.7(4) . . ? C26 N4 H4 116.2 . . ? C27 N4 H4 116.2 . . ? O1 C1 N1 125.5(4) . . ? O1 C1 C2 120.2(4) . . ? N1 C1 C2 114.3(4) . . ? C7 C2 C3 116.7(4) . . ? C7 C2 C1 121.2(4) . . ? C3 C2 C1 122.1(4) . . ? F1 C3 C4 117.1(4) . . ? F1 C3 C2 121.0(4) . . ? C4 C3 C2 121.8(4) . . ? F2 C4 C5 120.3(4) . . ? F2 C4 C3 120.0(4) . . ? C5 C4 C3 119.7(4) . . ? F3 C5 C6 119.9(4) . . ? F3 C5 C4 120.0(4) . . ? C6 C5 C4 120.1(4) . . ? F4 C6 C5 120.3(4) . . ? F4 C6 C7 119.8(4) . . ? C5 C6 C7 119.9(4) . . ? F5 C7 C2 121.4(4) . . ? F5 C7 C6 116.9(4) . . ? C2 C7 C6 121.7(4) . . ? N1 C8 C9 111.8(5) . . ? N1 C8 H8A 109.2 . . ? C9 C8 H8A 109.2 . . ? N1 C8 H8B 109.2 . . ? C9 C8 H8B 109.2 . . ? H8A C8 H8B 107.9 . . ? C8 C9 C10 113.3(4) . . ? C8 C9 H9A 108.9 . . ? C10 C9 H9A 108.9 . . ? C8 C9 H9B 108.9 . . ? C10 C9 H9B 108.9 . . ? H9A C9 H9B 107.7 . . ? O2 C10 N2 123.8(4) . . ? O2 C10 C9 121.1(4) . . ? N2 C10 C9 115.1(4) . . ? C16 C11 C12 120.3(4) . . ? C16 C11 N2 116.2(4) . . ? C12 C11 N2 123.4(4) . . ? C13 C12 C11 119.0(4) . . ? C13 C12 H12 120.5 . . ? C11 C12 H12 120.5 . . ? C12 C13 C14 122.0(5) . . ? C12 C13 H13 119.0 . . ? C14 C13 H13 119.0 . . ? C13 C14 C15 118.4(4) . . ? C13 C14 H14 120.8 . . ? C15 C14 H14 120.8 . . ? C14 C15 C16 120.8(4) . . ? C14 C15 H15 119.6 . . ? C16 C15 H15 119.6 . . ? C11 C16 C15 119.5(4) . . ? C11 C16 H16 120.2 . . ? C15 C16 H16 120.2 . . ? O3 C17 N3 123.7(4) . . ? O3 C17 C18 120.8(4) . . ? N3 C17 C18 115.5(4) . . ? C19 C18 C23 116.0(4) . . ? C19 C18 C17 121.8(4) . . ? C23 C18 C17 122.2(4) . . ? F6 C19 C18 120.9(4) . . ? F6 C19 C20 117.0(4) . . ? C18 C19 C20 122.1(4) . . ? F7 C20 C21 120.4(4) . . ? F7 C20 C19 119.6(4) . . ? C21 C20 C19 120.0(4) . . ? F8 C21 C20 120.3(4) . . ? F8 C21 C22 120.3(4) . . ? C20 C21 C22 119.4(4) . . ? F9 C22 C23 120.3(4) . . ? F9 C22 C21 119.9(4) . . ? C23 C22 C21 119.8(4) . . ? F10 C23 C22 116.6(4) . . ? F10 C23 C18 120.5(4) . . ? C22 C23 C18 122.9(4) . . ? N3 C24 C25 110.2(4) . . ? N3 C24 H24A 109.6 . . ? C25 C24 H24A 109.6 . . ? N3 C24 H24B 109.6 . . ? C25 C24 H24B 109.6 . . ? H24A C24 H24B 108.1 . . ? C24 C25 C26 112.5(4) . . ? C24 C25 H25A 109.1 . . ? C26 C25 H25A 109.1 . . ? C24 C25 H25B 109.1 . . ? C26 C25 H25B 109.1 . . ? H25A C25 H25B 107.8 . . ? O4 C26 N4 124.3(4) . . ? O4 C26 C25 121.1(4) . . ? N4 C26 C25 114.6(4) . . ? C28 C27 C32 119.5(4) . . ? C28 C27 N4 124.5(4) . . ? C32 C27 N4 116.1(4) . . ? C27 C28 C29 119.4(4) . . ? C27 C28 H28 120.3 . . ? C29 C28 H28 120.3 . . ? C28 C29 C30 121.0(4) . . ? C28 C29 H29 119.5 . . ? C30 C29 H29 119.5 . . ? C31 C30 C29 118.9(4) . . ? C31 C30 H30 120.5 . . ? C29 C30 H30 120.5 . . ? C32 C31 C30 121.2(5) . . ? C32 C31 H31 119.4 . . ? C30 C31 H31 119.4 . . ? C31 C32 C27 119.9(4) . . ? C31 C32 H32 120.0 . . ? C27 C32 H32 120.0 . . ? 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 C8 N1 C1 O1 -4.9(8) . . . . ? C8 N1 C1 C2 173.4(4) . . . . ? O1 C1 C2 C7 -45.4(6) . . . . ? N1 C1 C2 C7 136.3(4) . . . . ? O1 C1 C2 C3 134.3(5) . . . . ? N1 C1 C2 C3 -44.1(6) . . . . ? C7 C2 C3 F1 177.7(4) . . . . ? C1 C2 C3 F1 -1.9(6) . . . . ? C7 C2 C3 C4 -1.4(6) . . . . ? C1 C2 C3 C4 178.9(4) . . . . ? F1 C3 C4 F2 3.2(6) . . . . ? C2 C3 C4 F2 -177.7(4) . . . . ? F1 C3 C4 C5 -177.9(4) . . . . ? C2 C3 C4 C5 1.2(7) . . . . ? F2 C4 C5 F3 -1.7(7) . . . . ? C3 C4 C5 F3 179.5(4) . . . . ? F2 C4 C5 C6 178.2(4) . . . . ? C3 C4 C5 C6 -0.7(7) . . . . ? F3 C5 C6 F4 0.9(7) . . . . ? C4 C5 C6 F4 -179.0(4) . . . . ? F3 C5 C6 C7 -179.7(4) . . . . ? C4 C5 C6 C7 0.4(7) . . . . ? C3 C2 C7 F5 178.6(4) . . . . ? C1 C2 C7 F5 -1.8(6) . . . . ? C3 C2 C7 C6 1.2(6) . . . . ? C1 C2 C7 C6 -179.2(4) . . . . ? F4 C6 C7 F5 1.1(6) . . . . ? C5 C6 C7 F5 -178.2(4) . . . . ? F4 C6 C7 C2 178.7(4) . . . . ? C5 C6 C7 C2 -0.7(7) . . . . ? C1 N1 C8 C9 -103.4(6) . . . . ? N1 C8 C9 C10 178.2(5) . . . . ? C11 N2 C10 O2 -3.6(8) . . . . ? C11 N2 C10 C9 174.6(5) . . . . ? C8 C9 C10 O2 -41.2(8) . . . . ? C8 C9 C10 N2 140.6(5) . . . . ? C10 N2 C11 C16 -160.7(5) . . . . ? C10 N2 C11 C12 19.4(7) . . . . ? C16 C11 C12 C13 0.4(6) . . . . ? N2 C11 C12 C13 -179.8(4) . . . . ? C11 C12 C13 C14 -0.6(7) . . . . ? C12 C13 C14 C15 0.0(7) . . . . ? C13 C14 C15 C16 0.9(7) . . . . ? C12 C11 C16 C15 0.5(7) . . . . ? N2 C11 C16 C15 -179.3(4) . . . . ? C14 C15 C16 C11 -1.2(7) . . . . ? C24 N3 C17 O3 3.9(8) . . . . ? C24 N3 C17 C18 -174.0(4) . . . . ? O3 C17 C18 C19 42.3(6) . . . . ? N3 C17 C18 C19 -139.7(4) . . . . ? O3 C17 C18 C23 -137.6(4) . . . . ? N3 C17 C18 C23 40.3(6) . . . . ? C23 C18 C19 F6 -178.5(4) . . . . ? C17 C18 C19 F6 1.6(6) . . . . ? C23 C18 C19 C20 -0.3(6) . . . . ? C17 C18 C19 C20 179.8(4) . . . . ? F6 C19 C20 F7 -0.7(6) . . . . ? C18 C19 C20 F7 -179.0(4) . . . . ? F6 C19 C20 C21 178.5(4) . . . . ? C18 C19 C20 C21 0.2(7) . . . . ? F7 C20 C21 F8 -0.5(7) . . . . ? C19 C20 C21 F8 -179.7(4) . . . . ? F7 C20 C21 C22 178.8(4) . . . . ? C19 C20 C21 C22 -0.3(7) . . . . ? F8 C21 C22 F9 0.3(6) . . . . ? C20 C21 C22 F9 -179.0(4) . . . . ? F8 C21 C22 C23 179.9(4) . . . . ? C20 C21 C22 C23 0.5(6) . . . . ? F9 C22 C23 F10 -3.0(6) . . . . ? C21 C22 C23 F10 177.4(4) . . . . ? F9 C22 C23 C18 178.9(4) . . . . ? C21 C22 C23 C18 -0.6(7) . . . . ? C19 C18 C23 F10 -177.5(4) . . . . ? C17 C18 C23 F10 2.4(6) . . . . ? C19 C18 C23 C22 0.5(6) . . . . ? C17 C18 C23 C22 -179.6(4) . . . . ? C17 N3 C24 C25 162.7(5) . . . . ? N3 C24 C25 C26 -179.7(5) . . . . ? C27 N4 C26 O4 4.2(8) . . . . ? C27 N4 C26 C25 -175.4(5) . . . . ? C24 C25 C26 O4 -15.4(8) . . . . ? C24 C25 C26 N4 164.2(5) . . . . ? C26 N4 C27 C28 -18.3(7) . . . . ? C26 N4 C27 C32 161.9(5) . . . . ? C32 C27 C28 C29 0.0(7) . . . . ? N4 C27 C28 C29 -179.9(4) . . . . ? C27 C28 C29 C30 -0.5(7) . . . . ? C28 C29 C30 C31 0.4(8) . . . . ? C29 C30 C31 C32 0.2(8) . . . . ? C30 C31 C32 C27 -0.7(7) . . . . ? C28 C27 C32 C31 0.6(7) . . . . ? N4 C27 C32 C31 -179.5(4) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 O4 0.86 1.98 2.815(6) 164.3 1_655 N2 H2 O3 0.86 2.14 2.988(5) 171.2 1_655 N3 H3 O2 0.86 2.00 2.831(5) 160.6 1_545 N4 H4 O1 0.86 2.14 2.996(5) 171.0 1_545 _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.418 _refine_diff_density_min -0.335 _refine_diff_density_rms 0.086 _database_code_depnum_ccdc_archive 'CCDC 965772' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_cd212428 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H11 N O' _chemical_formula_weight 197.23 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.352(6) _cell_length_b 7.971(8) _cell_length_c 12.471(13) _cell_angle_alpha 73.23(2) _cell_angle_beta 79.202(19) _cell_angle_gamma 89.85(2) _cell_volume 499.6(9) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 863 _cell_measurement_theta_min 6.958 _cell_measurement_theta_max 51.794 _exptl_crystal_description prismatic _exptl_crystal_colour colorless _exptl_crystal_size_max 0.245 _exptl_crystal_size_mid 0.211 _exptl_crystal_size_min 0.147 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.311 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 208 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.11032 _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 1847 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0619 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.73 _diffrn_reflns_theta_max 25.50 _reflns_number_total 1847 _reflns_number_gt 1254 _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^)+(0.1227P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1849 _refine_ls_number_parameters 141 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0840 _refine_ls_R_factor_gt 0.0646 _refine_ls_wR_factor_ref 0.1886 _refine_ls_wR_factor_gt 0.1770 _refine_ls_goodness_of_fit_ref 0.960 _refine_ls_restrained_S_all 0.963 _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 N1 N 0.3127(4) 0.2518(3) 0.46428(19) 0.0435(6) Uani 1 1 d D . . O1 O -0.1191(3) 0.2439(3) 0.50066(15) 0.0560(7) Uani 1 1 d U . . C1 C 0.0833(5) 0.2459(4) 0.5335(2) 0.0421(7) Uani 1 1 d U . . C2 C 0.0942(5) 0.2387(3) 0.65440(19) 0.0364(6) Uani 1 1 d . . . C3 C -0.1088(5) 0.1521(3) 0.7387(2) 0.0413(7) Uani 1 1 d . . . H3 H -0.2402 0.0977 0.7194 0.050 Uiso 1 1 calc R . . C4 C -0.1170(5) 0.1462(4) 0.8508(2) 0.0440(7) Uani 1 1 d . . . H4 H -0.2534 0.0865 0.9067 0.053 Uiso 1 1 calc R . . C5 C 0.0731(5) 0.2272(4) 0.8813(2) 0.0435(7) Uani 1 1 d . . . H5 H 0.0649 0.2229 0.9572 0.052 Uiso 1 1 calc R . . C6 C 0.2769(5) 0.3154(4) 0.7983(2) 0.0452(7) Uani 1 1 d . . . H6 H 0.4055 0.3715 0.8182 0.054 Uiso 1 1 calc R . . C7 C 0.2886(5) 0.3196(3) 0.6856(2) 0.0417(7) Uani 1 1 d . . . H7 H 0.4273 0.3770 0.6301 0.050 Uiso 1 1 calc R . . C8 C 0.3526(5) 0.2580(3) 0.34684(19) 0.0365(6) Uani 1 1 d . . . C9 C 0.5661(5) 0.1828(4) 0.3051(2) 0.0422(7) Uani 1 1 d . . . H9 H 0.6712 0.1253 0.3540 0.051 Uiso 1 1 calc R . . C10 C 0.6251(5) 0.1920(4) 0.1911(2) 0.0443(7) Uani 1 1 d . . . H10 H 0.7696 0.1403 0.1639 0.053 Uiso 1 1 calc R . . C11 C 0.4724(5) 0.2770(4) 0.1171(2) 0.0435(7) Uani 1 1 d . . . H11 H 0.5137 0.2827 0.0402 0.052 Uiso 1 1 calc R . . C12 C 0.2589(5) 0.3531(3) 0.1576(2) 0.0420(7) Uani 1 1 d . . . H12 H 0.1554 0.4105 0.1078 0.050 Uiso 1 1 calc R . . C13 C 0.1963(5) 0.3450(3) 0.27228(19) 0.0409(7) Uani 1 1 d . . . H13 H 0.0517 0.3970 0.2993 0.049 Uiso 1 1 calc R . . H1 H 0.428(6) 0.246(5) 0.505(3) 0.109(16) Uiso 1 1 d 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 N1 0.0421(13) 0.0556(16) 0.0341(12) -0.0156(11) -0.0068(9) 0.0042(10) O1 0.0324(10) 0.1021(18) 0.0346(10) -0.0223(10) -0.0057(7) -0.0014(10) C1 0.0372(13) 0.0454(17) 0.0433(15) -0.0132(12) -0.0065(10) 0.0001(12) C2 0.0411(14) 0.0363(15) 0.0310(13) -0.0100(11) -0.0049(10) 0.0079(11) C3 0.0419(14) 0.0462(17) 0.0362(14) -0.0123(12) -0.0081(11) -0.0006(12) C4 0.0432(14) 0.0492(17) 0.0333(14) -0.0091(12) 0.0031(11) 0.0024(12) C5 0.0524(15) 0.0514(18) 0.0293(13) -0.0155(12) -0.0083(11) 0.0129(13) C6 0.0438(14) 0.0491(18) 0.0482(16) -0.0202(13) -0.0127(12) 0.0023(12) C7 0.0386(14) 0.0446(17) 0.0375(14) -0.0105(12) 0.0011(11) -0.0005(12) C8 0.0445(14) 0.0367(15) 0.0274(12) -0.0094(10) -0.0048(10) -0.0040(11) C9 0.0433(14) 0.0437(17) 0.0425(15) -0.0145(12) -0.0124(11) 0.0028(12) C10 0.0399(14) 0.0514(18) 0.0436(15) -0.0215(13) -0.0008(11) 0.0026(12) C11 0.0483(15) 0.0528(18) 0.0300(13) -0.0175(12) -0.0005(11) -0.0062(13) C12 0.0447(14) 0.0468(17) 0.0341(14) -0.0091(11) -0.0108(11) -0.0009(12) C13 0.0396(13) 0.0467(17) 0.0352(14) -0.0134(12) -0.0021(11) 0.0046(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C1 1.354(3) . ? N1 C8 1.426(3) . ? N1 H1 0.857(19) . ? O1 C1 1.229(3) . ? C1 C2 1.505(4) . ? C2 C3 1.385(4) . ? C2 C7 1.397(4) . ? C3 C4 1.378(3) . ? C3 H3 0.9300 . ? C4 C5 1.373(4) . ? C4 H4 0.9300 . ? C5 C6 1.384(4) . ? C5 H5 0.9300 . ? C6 C7 1.386(3) . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? C8 C9 1.374(4) . ? C8 C13 1.401(4) . ? C9 C10 1.377(3) . ? C9 H9 0.9300 . ? C10 C11 1.378(4) . ? C10 H10 0.9300 . ? C11 C12 1.373(4) . ? C11 H11 0.9300 . ? C12 C13 1.389(3) . ? C12 H12 0.9300 . ? C13 H13 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 C8 125.6(2) . . ? C1 N1 H1 108(2) . . ? C8 N1 H1 127(2) . . ? O1 C1 N1 122.7(3) . . ? O1 C1 C2 122.3(2) . . ? N1 C1 C2 115.0(2) . . ? C3 C2 C7 118.6(2) . . ? C3 C2 C1 117.1(2) . . ? C7 C2 C1 124.2(2) . . ? C4 C3 C2 120.4(2) . . ? C4 C3 H3 119.8 . . ? C2 C3 H3 119.8 . . ? C5 C4 C3 121.0(2) . . ? C5 C4 H4 119.5 . . ? C3 C4 H4 119.5 . . ? C4 C5 C6 119.6(2) . . ? C4 C5 H5 120.2 . . ? C6 C5 H5 120.2 . . ? C5 C6 C7 119.8(3) . . ? C5 C6 H6 120.1 . . ? C7 C6 H6 120.1 . . ? C6 C7 C2 120.6(2) . . ? C6 C7 H7 119.7 . . ? C2 C7 H7 119.7 . . ? C9 C8 C13 119.4(2) . . ? C9 C8 N1 117.0(2) . . ? C13 C8 N1 123.5(2) . . ? C8 C9 C10 120.3(2) . . ? C8 C9 H9 119.8 . . ? C10 C9 H9 119.8 . . ? C9 C10 C11 120.8(2) . . ? C9 C10 H10 119.6 . . ? C11 C10 H10 119.6 . . ? C12 C11 C10 119.5(2) . . ? C12 C11 H11 120.3 . . ? C10 C11 H11 120.3 . . ? C11 C12 C13 120.5(2) . . ? C11 C12 H12 119.7 . . ? C13 C12 H12 119.7 . . ? C12 C13 C8 119.4(2) . . ? C12 C13 H13 120.3 . . ? C8 C13 H13 120.3 . . ? 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 C8 N1 C1 O1 0.6(4) . . . . ? C8 N1 C1 C2 179.5(2) . . . . ? O1 C1 C2 C3 28.9(4) . . . . ? N1 C1 C2 C3 -150.0(3) . . . . ? O1 C1 C2 C7 -148.1(3) . . . . ? N1 C1 C2 C7 32.9(4) . . . . ? C7 C2 C3 C4 -0.2(4) . . . . ? C1 C2 C3 C4 -177.4(2) . . . . ? C2 C3 C4 C5 0.8(4) . . . . ? C3 C4 C5 C6 -0.4(4) . . . . ? C4 C5 C6 C7 -0.6(4) . . . . ? C5 C6 C7 C2 1.2(4) . . . . ? C3 C2 C7 C6 -0.8(4) . . . . ? C1 C2 C7 C6 176.2(2) . . . . ? C1 N1 C8 C9 -150.0(3) . . . . ? C1 N1 C8 C13 34.1(4) . . . . ? C13 C8 C9 C10 -0.4(4) . . . . ? N1 C8 C9 C10 -176.4(2) . . . . ? C8 C9 C10 C11 0.2(4) . . . . ? C9 C10 C11 C12 -0.1(4) . . . . ? C10 C11 C12 C13 0.0(4) . . . . ? C11 C12 C13 C8 -0.1(4) . . . . ? C9 C8 C13 C12 0.3(4) . . . . ? N1 C8 C13 C12 176.1(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 O1 0.857(19) 2.42(3) 3.155(4) 145(3) 1_655 _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.447 _refine_diff_density_min -0.331 _refine_diff_density_rms 0.066 _database_code_depnum_ccdc_archive 'CCDC 965773' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_cd213488 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H24 F5 N3 O3' _chemical_formula_weight 485.45 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 16.8272(18) _cell_length_b 9.5857(10) _cell_length_c 13.9962(14) _cell_angle_alpha 90.00 _cell_angle_beta 91.955(2) _cell_angle_gamma 90.00 _cell_volume 2256.3(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2513 _cell_measurement_theta_min 4.844 _cell_measurement_theta_max 45.950 _exptl_crystal_description prismatic _exptl_crystal_colour colorless _exptl_crystal_size_max 0.213 _exptl_crystal_size_mid 0.156 _exptl_crystal_size_min 0.112 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.429 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1008 _exptl_absorpt_coefficient_mu 0.123 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.39148 _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 12875 _diffrn_reflns_av_R_equivalents 0.0388 _diffrn_reflns_av_sigmaI/netI 0.0394 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.42 _diffrn_reflns_theta_max 25.50 _reflns_number_total 4208 _reflns_number_gt 2747 _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^)+(0.0868P)^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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0024(8) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4208 _refine_ls_number_parameters 320 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0704 _refine_ls_R_factor_gt 0.0442 _refine_ls_wR_factor_ref 0.1439 _refine_ls_wR_factor_gt 0.1268 _refine_ls_goodness_of_fit_ref 0.982 _refine_ls_restrained_S_all 0.982 _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 0.16943(9) 0.63324(12) 1.36020(8) 0.0818(4) Uani 1 1 d . . . F2 F 0.04838(9) 0.78551(14) 1.42182(10) 0.0934(5) Uani 1 1 d . . . F3 F -0.01990(9) 0.98243(18) 1.30737(12) 0.1102(6) Uani 1 1 d . . . F4 F 0.03258(10) 1.02159(17) 1.12976(12) 0.1125(6) Uani 1 1 d . . . F5 F 0.15060(9) 0.86590(13) 1.06444(9) 0.0845(4) Uani 1 1 d . . . N1 N 0.28766(11) 0.71346(18) 1.13322(11) 0.0584(5) Uani 1 1 d . . . N2 N 0.52762(10) 0.63992(17) 0.71173(12) 0.0622(5) Uani 1 1 d . . . N3 N 0.75553(11) 0.72169(17) 0.27611(12) 0.0590(5) Uani 1 1 d . . . O1 O 0.22301(10) 0.52274(14) 1.18198(11) 0.0772(5) Uani 1 1 d . . . O2 O 0.47845(9) 0.44222(12) 0.77014(10) 0.0688(4) Uani 1 1 d . . . O3 O 0.71428(9) 0.50759(12) 0.32042(10) 0.0671(4) Uani 1 1 d . . . C1 C 0.13484(13) 0.72527(19) 1.29968(14) 0.0577(5) Uani 1 1 d . . . C2 C 0.07327(14) 0.8034(2) 1.33323(15) 0.0673(6) Uani 1 1 d . . . C3 C 0.03924(14) 0.9030(2) 1.27558(19) 0.0747(7) Uani 1 1 d . . . C4 C 0.06579(14) 0.9234(2) 1.18572(18) 0.0735(6) Uani 1 1 d . . . C5 C 0.12745(13) 0.8433(2) 1.15330(15) 0.0615(6) Uani 1 1 d . . . C6 C 0.16352(12) 0.74233(17) 1.20979(13) 0.0509(5) Uani 1 1 d . . . C7 C 0.22834(13) 0.64903(19) 1.17376(12) 0.0537(5) Uani 1 1 d . . . C8 C 0.35035(14) 0.6396(2) 1.08480(15) 0.0652(6) Uani 1 1 d . . . H8A H 0.3380 0.5408 1.0832 0.078 Uiso 1 1 calc R . . H8B H 0.4002 0.6514 1.1209 0.078 Uiso 1 1 calc R . . C9 C 0.36007(12) 0.69051(18) 0.98515(13) 0.0551(5) Uani 1 1 d . . . H9A H 0.3783 0.7865 0.9876 0.066 Uiso 1 1 calc R . . H9B H 0.3086 0.6894 0.9518 0.066 Uiso 1 1 calc R . . C10 C 0.41800(12) 0.60529(18) 0.92837(13) 0.0532(5) Uani 1 1 d . . . H10A H 0.4697 0.6071 0.9611 0.064 Uiso 1 1 calc R . . H10B H 0.4001 0.5091 0.9261 0.064 Uiso 1 1 calc R . . C11 C 0.42635(13) 0.65743(18) 0.82812(15) 0.0610(6) Uani 1 1 d . . . H11A H 0.4469 0.7520 0.8308 0.073 Uiso 1 1 calc R . . H11B H 0.3740 0.6608 0.7969 0.073 Uiso 1 1 calc R . . C12 C 0.48020(12) 0.56998(18) 0.76813(13) 0.0516(5) Uani 1 1 d . . . C13 C 0.57804(14) 0.57201(19) 0.64371(16) 0.0683(6) Uani 1 1 d . . . H13A H 0.5496 0.4939 0.6147 0.082 Uiso 1 1 calc R . . H13B H 0.6251 0.5357 0.6771 0.082 Uiso 1 1 calc R . . C14 C 0.60263(12) 0.67030(18) 0.56715(14) 0.0569(5) Uani 1 1 d . . . H14A H 0.6340 0.7448 0.5964 0.068 Uiso 1 1 calc R . . H14B H 0.5553 0.7119 0.5376 0.068 Uiso 1 1 calc R . . C15 C 0.65027(13) 0.60273(18) 0.49057(15) 0.0598(5) Uani 1 1 d . . . H15A H 0.6973 0.5603 0.5202 0.072 Uiso 1 1 calc R . . H15B H 0.6187 0.5289 0.4609 0.072 Uiso 1 1 calc R . . C16 C 0.67551(14) 0.70168(18) 0.41456(15) 0.0611(6) Uani 1 1 d . . . H16A H 0.7107 0.7711 0.4435 0.073 Uiso 1 1 calc R . . H16B H 0.6289 0.7499 0.3888 0.073 Uiso 1 1 calc R . . C17 C 0.71706(12) 0.63321(18) 0.33404(14) 0.0517(5) Uani 1 1 d . . . C18 C 0.79488(12) 0.69142(19) 0.19151(14) 0.0537(5) Uani 1 1 d . . . C19 C 0.78497(13) 0.5691(2) 0.14057(14) 0.0626(6) Uani 1 1 d . . . H19 H 0.7519 0.4995 0.1629 0.075 Uiso 1 1 calc R . . C20 C 0.82392(14) 0.5502(2) 0.05662(16) 0.0744(6) Uani 1 1 d . . . H20 H 0.8175 0.4667 0.0234 0.089 Uiso 1 1 calc R . . C21 C 0.87179(16) 0.6513(3) 0.02121(18) 0.0852(7) Uani 1 1 d . . . H21 H 0.8976 0.6377 -0.0358 0.102 Uiso 1 1 calc R . . C22 C 0.88111(17) 0.7727(3) 0.07104(19) 0.0925(8) Uani 1 1 d . . . H22 H 0.9131 0.8428 0.0472 0.111 Uiso 1 1 calc R . . C23 C 0.84424(15) 0.7933(2) 0.15571(17) 0.0772(7) Uani 1 1 d . . . H23 H 0.8524 0.8760 0.1893 0.093 Uiso 1 1 calc R . . H2 H 0.5281(13) 0.730(2) 0.7123(15) 0.074(7) Uiso 1 1 d . . . H1 H 0.2898(11) 0.798(2) 1.1308(13) 0.056(6) Uiso 1 1 d . . . H3 H 0.7595(14) 0.802(2) 0.2955(16) 0.075(7) Uiso 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 F1 0.1234(11) 0.0681(8) 0.0556(8) 0.0122(6) 0.0249(7) 0.0204(7) F2 0.1098(12) 0.0956(10) 0.0779(9) -0.0012(7) 0.0504(8) 0.0032(8) F3 0.0855(11) 0.1133(12) 0.1339(14) -0.0041(9) 0.0360(9) 0.0339(8) F4 0.1133(13) 0.1141(12) 0.1099(13) 0.0326(10) 0.0016(10) 0.0428(10) F5 0.1076(11) 0.0929(9) 0.0535(8) 0.0163(6) 0.0114(7) 0.0096(8) N1 0.0799(13) 0.0385(10) 0.0583(11) -0.0036(8) 0.0245(9) 0.0024(8) N2 0.0832(13) 0.0303(9) 0.0758(12) -0.0004(7) 0.0410(10) 0.0011(8) N3 0.0797(12) 0.0375(9) 0.0614(11) -0.0014(8) 0.0246(9) -0.0047(8) O1 0.1090(13) 0.0403(8) 0.0841(11) -0.0017(7) 0.0315(9) -0.0012(7) O2 0.0921(11) 0.0286(7) 0.0883(11) 0.0025(6) 0.0409(8) 0.0030(6) O3 0.0971(11) 0.0362(8) 0.0699(9) 0.0003(6) 0.0317(8) -0.0002(7) C1 0.0740(14) 0.0465(11) 0.0535(12) 0.0005(9) 0.0138(10) -0.0030(9) C2 0.0751(15) 0.0666(14) 0.0619(14) -0.0063(11) 0.0261(12) -0.0050(11) C3 0.0615(14) 0.0747(16) 0.0891(18) -0.0047(13) 0.0173(13) 0.0068(11) C4 0.0699(16) 0.0698(14) 0.0808(17) 0.0101(12) 0.0007(13) 0.0115(11) C5 0.0717(14) 0.0622(13) 0.0511(13) 0.0037(10) 0.0074(10) -0.0036(10) C6 0.0619(13) 0.0431(10) 0.0482(11) -0.0030(8) 0.0106(9) -0.0048(8) C7 0.0806(15) 0.0412(11) 0.0401(10) -0.0021(8) 0.0115(10) -0.0015(9) C8 0.0798(15) 0.0560(12) 0.0613(13) -0.0027(9) 0.0236(11) 0.0116(10) C9 0.0663(13) 0.0405(10) 0.0596(12) -0.0011(8) 0.0203(10) 0.0032(9) C10 0.0600(12) 0.0400(10) 0.0606(13) -0.0015(8) 0.0165(10) 0.0033(8) C11 0.0738(14) 0.0366(10) 0.0744(14) 0.0038(9) 0.0310(11) 0.0076(9) C12 0.0658(13) 0.0329(10) 0.0575(12) 0.0008(8) 0.0207(9) 0.0036(8) C13 0.0900(16) 0.0417(11) 0.0760(15) 0.0038(9) 0.0436(12) 0.0096(10) C14 0.0660(13) 0.0417(10) 0.0644(13) 0.0031(8) 0.0228(10) 0.0041(9) C15 0.0722(14) 0.0433(11) 0.0657(13) 0.0046(9) 0.0264(11) 0.0035(9) C16 0.0785(15) 0.0398(11) 0.0665(13) 0.0016(9) 0.0251(11) 0.0029(9) C17 0.0626(12) 0.0356(10) 0.0577(12) 0.0030(8) 0.0157(9) 0.0019(8) C18 0.0574(12) 0.0508(11) 0.0538(12) 0.0044(9) 0.0165(9) 0.0027(9) C19 0.0751(15) 0.0590(13) 0.0546(13) -0.0032(9) 0.0148(11) -0.0056(10) C20 0.0871(17) 0.0775(15) 0.0595(14) -0.0110(11) 0.0163(12) -0.0015(12) C21 0.0831(17) 0.113(2) 0.0613(15) -0.0060(14) 0.0286(12) -0.0075(15) C22 0.096(2) 0.100(2) 0.0847(18) 0.0009(15) 0.0430(15) -0.0295(15) C23 0.0909(18) 0.0623(14) 0.0808(17) -0.0033(11) 0.0359(13) -0.0157(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag F1 C1 1.342(2) . ? F2 C2 1.333(2) . ? F3 C3 1.341(3) . ? F4 C4 1.335(2) . ? F5 C5 1.334(2) . ? N1 C7 1.318(2) . ? N1 C8 1.457(2) . ? N1 H1 0.808(19) . ? N2 C12 1.324(2) . ? N2 C13 1.451(2) . ? N2 H2 0.87(2) . ? N3 C17 1.353(2) . ? N3 C18 1.406(2) . ? N3 H3 0.82(2) . ? O1 C7 1.220(2) . ? O2 C12 1.225(2) . ? O3 C17 1.2198(19) . ? C1 C6 1.373(3) . ? C1 C2 1.374(3) . ? C2 C3 1.363(3) . ? C3 C4 1.363(3) . ? C4 C5 1.380(3) . ? C5 C6 1.377(3) . ? C6 C7 1.511(3) . ? C8 C9 1.492(3) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.517(2) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C11 1.501(3) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.510(2) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C13 C14 1.496(2) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 C15 1.506(3) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 C16 1.498(3) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 C17 1.498(3) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C18 C19 1.379(3) . ? C18 C23 1.387(3) . ? C19 C20 1.377(3) . ? C19 H19 0.9300 . ? C20 C21 1.365(3) . ? C20 H20 0.9300 . ? C21 C22 1.363(3) . ? C21 H21 0.9300 . ? C22 C23 1.371(3) . ? C22 H22 0.9300 . ? C23 H23 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 C7 N1 C8 122.92(17) . . ? C7 N1 H1 121.4(14) . . ? C8 N1 H1 115.5(14) . . ? C12 N2 C13 122.82(16) . . ? C12 N2 H2 120.5(14) . . ? C13 N2 H2 116.7(14) . . ? C17 N3 C18 128.58(16) . . ? C17 N3 H3 115.3(16) . . ? C18 N3 H3 115.9(16) . . ? F1 C1 C6 119.89(18) . . ? F1 C1 C2 117.30(18) . . ? C6 C1 C2 122.75(19) . . ? F2 C2 C3 120.1(2) . . ? F2 C2 C1 120.8(2) . . ? C3 C2 C1 119.1(2) . . ? F3 C3 C2 120.2(2) . . ? F3 C3 C4 119.7(2) . . ? C2 C3 C4 120.2(2) . . ? F4 C4 C3 119.9(2) . . ? F4 C4 C5 120.3(2) . . ? C3 C4 C5 119.8(2) . . ? F5 C5 C6 120.82(19) . . ? F5 C5 C4 117.59(19) . . ? C6 C5 C4 121.6(2) . . ? C1 C6 C5 116.61(18) . . ? C1 C6 C7 121.06(17) . . ? C5 C6 C7 122.24(17) . . ? O1 C7 N1 124.40(18) . . ? O1 C7 C6 119.99(18) . . ? N1 C7 C6 115.61(15) . . ? N1 C8 C9 112.35(17) . . ? N1 C8 H8A 109.1 . . ? C9 C8 H8A 109.1 . . ? N1 C8 H8B 109.1 . . ? C9 C8 H8B 109.1 . . ? H8A C8 H8B 107.9 . . ? C8 C9 C10 113.99(16) . . ? C8 C9 H9A 108.8 . . ? C10 C9 H9A 108.8 . . ? C8 C9 H9B 108.8 . . ? C10 C9 H9B 108.8 . . ? H9A C9 H9B 107.7 . . ? C11 C10 C9 113.13(15) . . ? C11 C10 H10A 109.0 . . ? C9 C10 H10A 109.0 . . ? C11 C10 H10B 109.0 . . ? C9 C10 H10B 109.0 . . ? H10A C10 H10B 107.8 . . ? C10 C11 C12 114.33(15) . . ? C10 C11 H11A 108.7 . . ? C12 C11 H11A 108.7 . . ? C10 C11 H11B 108.7 . . ? C12 C11 H11B 108.7 . . ? H11A C11 H11B 107.6 . . ? O2 C12 N2 122.36(16) . . ? O2 C12 C11 121.78(16) . . ? N2 C12 C11 115.83(16) . . ? N2 C13 C14 111.69(15) . . ? N2 C13 H13A 109.3 . . ? C14 C13 H13A 109.3 . . ? N2 C13 H13B 109.3 . . ? C14 C13 H13B 109.3 . . ? H13A C13 H13B 107.9 . . ? C13 C14 C15 113.93(15) . . ? C13 C14 H14A 108.8 . . ? C15 C14 H14A 108.8 . . ? C13 C14 H14B 108.8 . . ? C15 C14 H14B 108.8 . . ? H14A C14 H14B 107.7 . . ? C16 C15 C14 113.81(15) . . ? C16 C15 H15A 108.8 . . ? C14 C15 H15A 108.8 . . ? C16 C15 H15B 108.8 . . ? C14 C15 H15B 108.8 . . ? H15A C15 H15B 107.7 . . ? C15 C16 C17 114.07(15) . . ? C15 C16 H16A 108.7 . . ? C17 C16 H16A 108.7 . . ? C15 C16 H16B 108.7 . . ? C17 C16 H16B 108.7 . . ? H16A C16 H16B 107.6 . . ? O3 C17 N3 122.79(17) . . ? O3 C17 C16 122.26(17) . . ? N3 C17 C16 114.91(16) . . ? C19 C18 C23 118.36(19) . . ? C19 C18 N3 123.95(18) . . ? C23 C18 N3 117.64(18) . . ? C20 C19 C18 120.1(2) . . ? C20 C19 H19 120.0 . . ? C18 C19 H19 120.0 . . ? C21 C20 C19 121.3(2) . . ? C21 C20 H20 119.3 . . ? C19 C20 H20 119.3 . . ? C22 C21 C20 118.7(2) . . ? C22 C21 H21 120.7 . . ? C20 C21 H21 120.7 . . ? C21 C22 C23 121.2(2) . . ? C21 C22 H22 119.4 . . ? C23 C22 H22 119.4 . . ? C22 C23 C18 120.3(2) . . ? C22 C23 H23 119.8 . . ? C18 C23 H23 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 F1 C1 C2 F2 -1.4(3) . . . . ? C6 C1 C2 F2 -178.53(18) . . . . ? F1 C1 C2 C3 176.7(2) . . . . ? C6 C1 C2 C3 -0.4(3) . . . . ? F2 C2 C3 F3 -0.6(4) . . . . ? C1 C2 C3 F3 -178.7(2) . . . . ? F2 C2 C3 C4 178.6(2) . . . . ? C1 C2 C3 C4 0.5(4) . . . . ? F3 C3 C4 F4 -0.4(4) . . . . ? C2 C3 C4 F4 -179.6(2) . . . . ? F3 C3 C4 C5 179.0(2) . . . . ? C2 C3 C4 C5 -0.2(4) . . . . ? F4 C4 C5 F5 -1.5(3) . . . . ? C3 C4 C5 F5 179.1(2) . . . . ? F4 C4 C5 C6 179.2(2) . . . . ? C3 C4 C5 C6 -0.2(4) . . . . ? F1 C1 C6 C5 -177.00(17) . . . . ? C2 C1 C6 C5 0.1(3) . . . . ? F1 C1 C6 C7 6.2(3) . . . . ? C2 C1 C6 C7 -176.68(18) . . . . ? F5 C5 C6 C1 -179.05(17) . . . . ? C4 C5 C6 C1 0.2(3) . . . . ? F5 C5 C6 C7 -2.3(3) . . . . ? C4 C5 C6 C7 177.0(2) . . . . ? C8 N1 C7 O1 6.3(3) . . . . ? C8 N1 C7 C6 -172.70(18) . . . . ? C1 C6 C7 O1 48.4(3) . . . . ? C5 C6 C7 O1 -128.1(2) . . . . ? C1 C6 C7 N1 -132.5(2) . . . . ? C5 C6 C7 N1 50.9(3) . . . . ? C7 N1 C8 C9 126.1(2) . . . . ? N1 C8 C9 C10 -173.25(17) . . . . ? C8 C9 C10 C11 179.48(18) . . . . ? C9 C10 C11 C12 -176.82(17) . . . . ? C13 N2 C12 O2 3.7(3) . . . . ? C13 N2 C12 C11 -174.6(2) . . . . ? C10 C11 C12 O2 42.1(3) . . . . ? C10 C11 C12 N2 -139.58(19) . . . . ? C12 N2 C13 C14 159.8(2) . . . . ? N2 C13 C14 C15 -175.85(19) . . . . ? C13 C14 C15 C16 -179.40(19) . . . . ? C14 C15 C16 C17 -175.22(18) . . . . ? C18 N3 C17 O3 2.8(4) . . . . ? C18 N3 C17 C16 -175.1(2) . . . . ? C15 C16 C17 O3 16.0(3) . . . . ? C15 C16 C17 N3 -166.08(19) . . . . ? C17 N3 C18 C19 16.1(3) . . . . ? C17 N3 C18 C23 -166.4(2) . . . . ? C23 C18 C19 C20 0.3(3) . . . . ? N3 C18 C19 C20 177.8(2) . . . . ? C18 C19 C20 C21 -1.0(4) . . . . ? C19 C20 C21 C22 0.4(4) . . . . ? C20 C21 C22 C23 0.8(4) . . . . ? C21 C22 C23 C18 -1.5(4) . . . . ? C19 C18 C23 C22 0.9(4) . . . . ? N3 C18 C23 C22 -176.8(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N3 H3 O1 0.82(2) 2.16(2) 2.964(2) 169(2) 2_656 N1 H1 O3 0.808(19) 2.13(2) 2.894(2) 158.3(18) 2_656 N2 H2 O2 0.87(2) 2.05(2) 2.911(2) 173(2) 2_656 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.191 _refine_diff_density_min -0.147 _refine_diff_density_rms 0.036 _database_code_depnum_ccdc_archive 'CCDC 965774' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_cd212237 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H6 F5 N O' _chemical_formula_weight 287.19 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 5.434(4) _cell_length_b 9.157(7) _cell_length_c 24.300(19) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1209.1(16) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3330 _cell_measurement_theta_min 4.754 _cell_measurement_theta_max 49.680 _exptl_crystal_description prismatic _exptl_crystal_colour colorless _exptl_crystal_size_max 0.331 _exptl_crystal_size_mid 0.224 _exptl_crystal_size_min 0.156 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.578 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 576 _exptl_absorpt_coefficient_mu 0.153 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.26378 _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 7275 _diffrn_reflns_av_R_equivalents 0.0402 _diffrn_reflns_av_sigmaI/netI 0.0334 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 2.38 _diffrn_reflns_theta_max 26.00 _reflns_number_total 2383 _reflns_number_gt 2014 _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^)+(0.0639P)^2^+0.0567P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.0(8) _chemical_absolute_configuration unk _refine_ls_number_reflns 2383 _refine_ls_number_parameters 185 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0454 _refine_ls_R_factor_gt 0.0377 _refine_ls_wR_factor_ref 0.1093 _refine_ls_wR_factor_gt 0.1027 _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_restrained_S_all 1.026 _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 O1 O -0.0925(4) -0.04044(14) 0.23130(6) 0.0798(5) Uani 1 1 d . . . C7 C -0.0497(3) 0.08331(17) 0.24642(8) 0.0523(4) Uani 1 1 d . . . C8 C 0.1128(4) 0.17591(19) 0.15897(7) 0.0543(4) Uani 1 1 d . . . N1 N 0.0426(3) 0.18806(16) 0.21489(6) 0.0561(4) Uani 1 1 d D . . F5 F 0.2421(3) -0.01037(16) 0.33447(6) 0.0889(5) Uani 1 1 d . . . F3 F -0.2429(4) 0.2163(2) 0.46793(6) 0.1187(7) Uani 1 1 d . . . C6 C -0.0973(4) 0.12695(19) 0.30526(7) 0.0514(4) Uani 1 1 d . . . F1 F -0.4397(3) 0.2687(2) 0.28179(6) 0.1014(5) Uani 1 1 d . . . F2 F -0.5350(3) 0.3273(2) 0.38833(8) 0.1223(7) Uani 1 1 d . . . F4 F 0.1506(4) 0.0495(2) 0.44029(6) 0.1182(6) Uani 1 1 d . . . C5 C 0.0487(4) 0.0739(2) 0.34704(8) 0.0598(5) Uani 1 1 d . . . C13 C -0.0120(5) 0.0880(2) 0.12215(9) 0.0751(6) Uani 1 1 d . . . H13 H -0.1455 0.0321 0.1336 0.090 Uiso 1 1 calc R . . C9 C 0.3076(4) 0.2591(3) 0.14155(9) 0.0699(6) Uani 1 1 d . . . H9 H 0.3906 0.3185 0.1664 0.084 Uiso 1 1 calc R . . C1 C -0.2914(4) 0.2142(2) 0.32053(9) 0.0651(5) Uani 1 1 d . . . C4 C 0.0029(5) 0.1036(3) 0.40147(8) 0.0730(6) Uani 1 1 d . . . C12 C 0.0660(7) 0.0849(3) 0.06770(10) 0.0927(8) Uani 1 1 d U . . H12 H -0.0149 0.0251 0.0426 0.111 Uiso 1 1 calc R . . C3 C -0.1955(5) 0.1886(3) 0.41533(9) 0.0768(6) Uani 1 1 d . . . C2 C -0.3424(4) 0.2448(3) 0.37455(10) 0.0767(6) Uani 1 1 d . . . C11 C 0.2598(6) 0.1683(3) 0.05046(10) 0.0891(7) Uani 1 1 d U . . H11 H 0.3090 0.1661 0.0138 0.107 Uiso 1 1 calc R . . C10 C 0.3806(5) 0.2548(3) 0.08732(9) 0.0869(7) Uani 1 1 d . . . H10 H 0.5131 0.3113 0.0757 0.104 Uiso 1 1 calc R . . H1 H 0.078(4) 0.267(2) 0.2282(8) 0.065(6) Uiso 1 1 d 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 O1 0.1304(14) 0.0421(7) 0.0669(9) 0.0056(6) -0.0070(9) -0.0154(8) C7 0.0616(10) 0.0402(8) 0.0551(9) 0.0053(7) -0.0084(8) 0.0016(8) C8 0.0699(11) 0.0424(8) 0.0506(10) 0.0003(7) -0.0068(9) 0.0047(8) N1 0.0784(10) 0.0383(7) 0.0517(8) -0.0013(6) 0.0000(8) -0.0067(7) F5 0.0928(9) 0.0887(9) 0.0852(9) -0.0013(7) -0.0204(7) 0.0358(8) F3 0.1408(15) 0.1499(16) 0.0653(9) -0.0172(9) 0.0204(8) -0.0057(14) C6 0.0551(9) 0.0445(8) 0.0546(9) 0.0081(7) -0.0049(8) -0.0036(8) F1 0.0857(9) 0.1263(12) 0.0923(9) 0.0014(9) -0.0234(8) 0.0438(10) F2 0.0882(9) 0.1569(17) 0.1217(13) -0.0301(12) 0.0149(9) 0.0384(12) F4 0.1561(15) 0.1313(13) 0.0672(8) 0.0107(8) -0.0401(10) 0.0317(14) C5 0.0650(11) 0.0532(9) 0.0611(11) 0.0056(8) -0.0071(9) 0.0049(9) C13 0.0957(16) 0.0676(12) 0.0620(12) -0.0022(10) -0.0150(11) -0.0151(12) C9 0.0817(14) 0.0692(12) 0.0587(11) -0.0047(10) 0.0014(10) -0.0136(12) C1 0.0595(11) 0.0704(12) 0.0654(11) 0.0063(10) -0.0064(9) 0.0042(10) C4 0.0911(15) 0.0743(13) 0.0536(11) 0.0102(9) -0.0142(11) -0.0022(12) C12 0.132(2) 0.0854(15) 0.0604(13) -0.0134(11) -0.0225(13) -0.0120(15) C3 0.0858(14) 0.0878(15) 0.0568(12) -0.0033(11) 0.0083(11) -0.0099(13) C2 0.0609(12) 0.0850(14) 0.0843(15) -0.0068(13) 0.0096(11) 0.0033(13) C11 0.1184(19) 0.0957(17) 0.0533(12) -0.0048(12) 0.0054(13) 0.0118(14) C10 0.0945(16) 0.1004(18) 0.0659(13) -0.0017(14) 0.0164(12) -0.0117(16) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C7 1.214(2) . ? C7 N1 1.326(2) . ? C7 C6 1.507(3) . ? C8 C9 1.371(3) . ? C8 C13 1.381(3) . ? C8 N1 1.416(3) . ? N1 H1 0.812(16) . ? F5 C5 1.339(3) . ? F3 C3 1.328(3) . ? C6 C1 1.375(3) . ? C6 C5 1.377(3) . ? F1 C1 1.336(2) . ? F2 C2 1.333(3) . ? F4 C4 1.334(3) . ? C5 C4 1.373(3) . ? C13 C12 1.390(4) . ? C13 H13 0.9300 . ? C9 C10 1.377(3) . ? C9 H9 0.9300 . ? C1 C2 1.371(3) . ? C4 C3 1.371(4) . ? C12 C11 1.367(4) . ? C12 H12 0.9300 . ? C3 C2 1.373(4) . ? C11 C10 1.364(4) . ? C11 H11 0.9300 . ? C10 H10 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 O1 C7 N1 124.95(18) . . ? O1 C7 C6 120.13(16) . . ? N1 C7 C6 114.91(15) . . ? C9 C8 C13 120.17(19) . . ? C9 C8 N1 117.43(17) . . ? C13 C8 N1 122.37(19) . . ? C7 N1 C8 126.84(15) . . ? C7 N1 H1 120.1(15) . . ? C8 N1 H1 112.8(15) . . ? C1 C6 C5 116.64(19) . . ? C1 C6 C7 122.80(16) . . ? C5 C6 C7 120.49(18) . . ? F5 C5 C4 118.44(18) . . ? F5 C5 C6 119.15(18) . . ? C4 C5 C6 122.4(2) . . ? C8 C13 C12 118.6(2) . . ? C8 C13 H13 120.7 . . ? C12 C13 H13 120.7 . . ? C8 C9 C10 120.1(2) . . ? C8 C9 H9 119.9 . . ? C10 C9 H9 119.9 . . ? F1 C1 C2 118.5(2) . . ? F1 C1 C6 119.33(19) . . ? C2 C1 C6 122.17(19) . . ? F4 C4 C3 120.7(2) . . ? F4 C4 C5 119.9(2) . . ? C3 C4 C5 119.4(2) . . ? C11 C12 C13 121.0(2) . . ? C11 C12 H12 119.5 . . ? C13 C12 H12 119.5 . . ? F3 C3 C4 119.8(2) . . ? F3 C3 C2 120.7(2) . . ? C4 C3 C2 119.5(2) . . ? F2 C2 C1 121.0(2) . . ? F2 C2 C3 119.2(2) . . ? C1 C2 C3 119.8(2) . . ? C10 C11 C12 119.6(2) . . ? C10 C11 H11 120.2 . . ? C12 C11 H11 120.2 . . ? C11 C10 C9 120.4(3) . . ? C11 C10 H10 119.8 . . ? C9 C10 H10 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 O1 C7 N1 C8 -1.4(3) . . . . ? C6 C7 N1 C8 177.54(17) . . . . ? C9 C8 N1 C7 -147.0(2) . . . . ? C13 C8 N1 C7 35.0(3) . . . . ? O1 C7 C6 C1 -106.4(2) . . . . ? N1 C7 C6 C1 74.6(3) . . . . ? O1 C7 C6 C5 70.4(3) . . . . ? N1 C7 C6 C5 -108.6(2) . . . . ? C1 C6 C5 F5 -179.28(17) . . . . ? C7 C6 C5 F5 3.7(3) . . . . ? C1 C6 C5 C4 1.1(3) . . . . ? C7 C6 C5 C4 -175.89(18) . . . . ? C9 C8 C13 C12 0.7(3) . . . . ? N1 C8 C13 C12 178.6(2) . . . . ? C13 C8 C9 C10 -0.3(3) . . . . ? N1 C8 C9 C10 -178.4(2) . . . . ? C5 C6 C1 F1 -179.89(19) . . . . ? C7 C6 C1 F1 -3.0(3) . . . . ? C5 C6 C1 C2 -1.5(3) . . . . ? C7 C6 C1 C2 175.4(2) . . . . ? F5 C5 C4 F4 0.5(3) . . . . ? C6 C5 C4 F4 -179.9(2) . . . . ? F5 C5 C4 C3 -179.4(2) . . . . ? C6 C5 C4 C3 0.2(3) . . . . ? C8 C13 C12 C11 -1.0(4) . . . . ? F4 C4 C3 F3 -0.7(4) . . . . ? C5 C4 C3 F3 179.2(2) . . . . ? F4 C4 C3 C2 179.0(2) . . . . ? C5 C4 C3 C2 -1.1(3) . . . . ? F1 C1 C2 F2 -0.2(4) . . . . ? C6 C1 C2 F2 -178.6(2) . . . . ? F1 C1 C2 C3 179.0(2) . . . . ? C6 C1 C2 C3 0.7(4) . . . . ? F3 C3 C2 F2 -0.3(4) . . . . ? C4 C3 C2 F2 180.0(2) . . . . ? F3 C3 C2 C1 -179.6(2) . . . . ? C4 C3 C2 C1 0.7(4) . . . . ? C13 C12 C11 C10 0.8(4) . . . . ? C12 C11 C10 C9 -0.4(4) . . . . ? C8 C9 C10 C11 0.1(4) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 O1 0.812(16) 2.023(17) 2.822(3) 168(2) 3 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.153 _refine_diff_density_min -0.139 _refine_diff_density_rms 0.029 _database_code_depnum_ccdc_archive 'CCDC 965775'