# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email ks42@leicester.ac.uk loop_ _publ_author_name 'Michal Fornalczyk' 'Kuldip Singh' 'Alison Stuart' data_08013 _database_code_depnum_ccdc_archive 'CCDC 842560' #TrackingRef '08013.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H14 F2 O3' _chemical_formula_sum 'C13 H14 F2 O3' _chemical_formula_weight 256.24 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 12.556(2) _cell_length_b 14.418(3) _cell_length_c 13.450(2) _cell_angle_alpha 90.00 _cell_angle_beta 101.806(3) _cell_angle_gamma 90.00 _cell_volume 2383.6(7) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 980 _cell_measurement_theta_min 2.178 _cell_measurement_theta_max 26.336 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.428 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1072 _exptl_absorpt_coefficient_mu 0.120 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 2000 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 18192 _diffrn_reflns_av_R_equivalents 0.1454 _diffrn_reflns_av_sigmaI/netI 0.0986 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.66 _diffrn_reflns_theta_max 26.00 _reflns_number_total 4684 _reflns_number_gt 3369 _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^)+(0.0326P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4684 _refine_ls_number_parameters 329 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0894 _refine_ls_R_factor_gt 0.0574 _refine_ls_wR_factor_ref 0.1317 _refine_ls_wR_factor_gt 0.1198 _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_restrained_S_all 1.055 _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 0.46280(10) 0.13188(10) 0.56778(10) 0.0329(4) Uani 1 1 d . . . F2 F 0.30291(10) 0.17077(9) 0.59340(10) 0.0303(4) Uani 1 1 d . . . O1 O 0.24297(12) -0.00799(10) 0.58667(12) 0.0261(4) Uani 1 1 d . . . O2 O 0.41961(13) -0.04098(12) 0.60158(13) 0.0355(5) Uani 1 1 d . . . O3 O 0.35110(12) 0.04369(11) 0.37897(12) 0.0273(4) Uani 1 1 d . . . H3 H 0.4194 0.0423 0.3926 0.041 Uiso 1 1 calc R . . C1 C 0.1092(2) -0.10991(18) 0.6288(2) 0.0378(7) Uani 1 1 d . . . H1A H 0.0974 -0.0672 0.6822 0.057 Uiso 1 1 calc R . . H1B H 0.0942 -0.1735 0.6476 0.057 Uiso 1 1 calc R . . H1C H 0.0603 -0.0936 0.5646 0.057 Uiso 1 1 calc R . . C2 C 0.22457(19) -0.10291(16) 0.61651(19) 0.0290(6) Uani 1 1 d . . . H2A H 0.2747 -0.1183 0.6813 0.035 Uiso 1 1 calc R . . H2B H 0.2378 -0.1469 0.5638 0.035 Uiso 1 1 calc R . . C3 C 0.34352(18) 0.01141(17) 0.58047(17) 0.0246(5) Uani 1 1 d . . . C4 C 0.35521(18) 0.11056(16) 0.54173(18) 0.0250(5) Uani 1 1 d . . . C5 C 0.31425(17) 0.12194(16) 0.42632(17) 0.0232(5) Uani 1 1 d . . . C6 C 0.18937(17) 0.12619(16) 0.39673(18) 0.0258(5) Uani 1 1 d . . . H6A H 0.1563 0.0928 0.4472 0.031 Uiso 1 1 calc R . . H6B H 0.1631 0.0977 0.3292 0.031 Uiso 1 1 calc R . . C7 C 0.15953(18) 0.23025(16) 0.39453(19) 0.0267(6) Uani 1 1 d . . . H7A H 0.0965 0.2439 0.3391 0.032 Uiso 1 1 calc R . . H7B H 0.1424 0.2502 0.4599 0.032 Uiso 1 1 calc R . . C8 C 0.26090(18) 0.27687(16) 0.37619(17) 0.0240(5) Uani 1 1 d . . . C9 C 0.34808(17) 0.21607(16) 0.39208(17) 0.0226(5) Uani 1 1 d . . . C10 C 0.44947(18) 0.24373(16) 0.37693(17) 0.0239(5) Uani 1 1 d . . . H10 H 0.5088 0.2015 0.3872 0.029 Uiso 1 1 calc R . . C11 C 0.46247(19) 0.33428(16) 0.34649(18) 0.0276(6) Uani 1 1 d . . . H11 H 0.5310 0.3544 0.3350 0.033 Uiso 1 1 calc R . . C12 C 0.37518(19) 0.39548(17) 0.33288(18) 0.0282(6) Uani 1 1 d . . . H12 H 0.3853 0.4577 0.3135 0.034 Uiso 1 1 calc R . . C13 C 0.27393(19) 0.36770(16) 0.34704(18) 0.0273(6) Uani 1 1 d . . . H13 H 0.2146 0.4099 0.3370 0.033 Uiso 1 1 calc R . . F1A F 0.93356(10) 0.36541(10) 0.42632(10) 0.0317(4) Uani 1 1 d . . . F2A F 0.76159(10) 0.32847(9) 0.39376(10) 0.0315(4) Uani 1 1 d . . . O1A O 0.70761(12) 0.50929(11) 0.40072(12) 0.0262(4) Uani 1 1 d . . . O2A O 0.87923(12) 0.53861(12) 0.38727(13) 0.0331(4) Uani 1 1 d . . . O3A O 0.89593(12) 0.45714(11) 0.61012(12) 0.0265(4) Uani 1 1 d . . . H3A H 0.9619 0.4541 0.6068 0.040 Uiso 1 1 calc R . . C1A C 0.55932(19) 0.61607(18) 0.3664(2) 0.0364(6) Uani 1 1 d . . . H1A1 H 0.5194 0.5759 0.3127 0.055 Uiso 1 1 calc R . . H1A2 H 0.5382 0.6808 0.3512 0.055 Uiso 1 1 calc R . . H1A3 H 0.5420 0.5985 0.4317 0.055 Uiso 1 1 calc R . . C2A C 0.67862(18) 0.60551(16) 0.37204(19) 0.0270(6) Uani 1 1 d . . . H2A1 H 0.6966 0.6198 0.3054 0.032 Uiso 1 1 calc R . . H2A2 H 0.7196 0.6486 0.4232 0.032 Uiso 1 1 calc R . . C3A C 0.81054(18) 0.48763(17) 0.40731(17) 0.0238(5) Uani 1 1 d . . . C4A C 0.83582(18) 0.38865(16) 0.44746(18) 0.0248(5) Uani 1 1 d . . . C5A C 0.83979(17) 0.37763(16) 0.56172(17) 0.0234(5) Uani 1 1 d . . . C6A C 0.72524(18) 0.37563(17) 0.58682(19) 0.0287(6) Uani 1 1 d . . . H6A1 H 0.7239 0.4130 0.6483 0.034 Uiso 1 1 calc R . . H6A2 H 0.6709 0.4014 0.5296 0.034 Uiso 1 1 calc R . . C7A C 0.69926(18) 0.27349(17) 0.60509(19) 0.0290(6) Uani 1 1 d . . . H7A1 H 0.6639 0.2673 0.6641 0.035 Uiso 1 1 calc R . . H7A2 H 0.6510 0.2465 0.5445 0.035 Uiso 1 1 calc R . . C8A C 0.80872(18) 0.22721(16) 0.62542(17) 0.0243(5) Uani 1 1 d . . . C9A C 0.88823(17) 0.28513(16) 0.60108(16) 0.0225(5) Uani 1 1 d . . . C10A C 0.99521(18) 0.25573(17) 0.61449(17) 0.0261(6) Uani 1 1 d . . . H10A H 1.0496 0.2956 0.5986 0.031 Uiso 1 1 calc R . . C11A C 1.0216(2) 0.16713(17) 0.65156(18) 0.0306(6) Uani 1 1 d . . . H11A H 1.0946 0.1460 0.6605 0.037 Uiso 1 1 calc R . . C12A C 0.9429(2) 0.10940(17) 0.67557(18) 0.0314(6) Uani 1 1 d . . . H12A H 0.9624 0.0492 0.7017 0.038 Uiso 1 1 calc R . . C13A C 0.8357(2) 0.13839(17) 0.66197(18) 0.0294(6) Uani 1 1 d . . . H13A H 0.7815 0.0981 0.6774 0.035 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 0.0231(7) 0.0382(9) 0.0341(8) 0.0085(7) -0.0019(6) -0.0057(6) F2 0.0397(8) 0.0233(8) 0.0284(8) -0.0010(6) 0.0085(6) 0.0032(6) O1 0.0246(9) 0.0212(9) 0.0334(10) 0.0040(7) 0.0077(7) 0.0010(7) O2 0.0269(9) 0.0326(11) 0.0483(12) 0.0138(9) 0.0108(8) 0.0092(8) O3 0.0247(9) 0.0230(9) 0.0349(10) -0.0017(7) 0.0077(8) 0.0019(7) C1 0.0348(15) 0.0322(16) 0.0477(17) 0.0031(13) 0.0116(13) -0.0062(12) C2 0.0393(15) 0.0179(13) 0.0321(14) 0.0043(11) 0.0126(11) -0.0007(11) C3 0.0265(13) 0.0250(14) 0.0222(13) 0.0009(10) 0.0049(10) 0.0018(11) C4 0.0203(12) 0.0240(13) 0.0306(13) 0.0008(11) 0.0046(10) 0.0013(10) C5 0.0219(12) 0.0194(13) 0.0286(13) 0.0013(10) 0.0055(10) 0.0014(10) C6 0.0218(12) 0.0256(14) 0.0287(13) 0.0037(11) 0.0021(10) -0.0030(10) C7 0.0223(13) 0.0271(14) 0.0315(14) 0.0041(11) 0.0068(10) 0.0034(10) C8 0.0234(12) 0.0266(14) 0.0210(12) -0.0006(10) 0.0022(10) 0.0011(10) C9 0.0242(12) 0.0220(13) 0.0199(12) -0.0017(10) 0.0004(9) 0.0003(10) C10 0.0196(12) 0.0241(13) 0.0277(13) -0.0004(10) 0.0042(10) 0.0013(10) C11 0.0270(13) 0.0273(14) 0.0288(14) -0.0001(11) 0.0066(11) -0.0084(11) C12 0.0352(14) 0.0190(13) 0.0290(14) 0.0030(11) 0.0033(11) -0.0050(11) C13 0.0314(14) 0.0227(14) 0.0271(13) 0.0009(11) 0.0040(10) 0.0056(11) F1A 0.0306(8) 0.0351(9) 0.0326(8) 0.0066(6) 0.0135(6) 0.0104(6) F2A 0.0379(8) 0.0235(8) 0.0312(8) -0.0022(6) 0.0023(6) -0.0019(6) O1A 0.0241(9) 0.0220(9) 0.0329(10) 0.0050(7) 0.0066(7) -0.0001(7) O2A 0.0256(9) 0.0271(10) 0.0471(11) 0.0085(8) 0.0090(8) -0.0017(8) O3A 0.0239(8) 0.0219(9) 0.0342(10) -0.0023(7) 0.0074(7) -0.0012(7) C1A 0.0309(14) 0.0315(16) 0.0458(17) 0.0066(13) 0.0057(12) 0.0057(12) C2A 0.0284(13) 0.0217(13) 0.0295(14) 0.0040(11) 0.0029(10) 0.0031(10) C3A 0.0205(12) 0.0276(14) 0.0230(13) -0.0017(10) 0.0034(10) -0.0014(11) C4A 0.0205(12) 0.0240(13) 0.0299(13) -0.0008(11) 0.0053(10) 0.0003(10) C5A 0.0226(12) 0.0219(13) 0.0262(13) -0.0015(10) 0.0060(10) -0.0018(10) C6A 0.0268(13) 0.0276(15) 0.0330(14) 0.0031(11) 0.0098(11) 0.0033(11) C7A 0.0274(13) 0.0270(15) 0.0332(15) 0.0013(11) 0.0076(11) -0.0017(11) C8A 0.0258(13) 0.0250(14) 0.0221(13) -0.0016(10) 0.0048(10) -0.0017(10) C9A 0.0259(13) 0.0206(13) 0.0195(12) -0.0010(10) 0.0010(10) 0.0006(10) C10A 0.0256(13) 0.0256(14) 0.0270(13) -0.0021(11) 0.0053(10) -0.0011(11) C11A 0.0284(13) 0.0325(15) 0.0289(14) 0.0002(11) 0.0009(11) 0.0102(11) C12A 0.0427(15) 0.0222(14) 0.0274(14) 0.0021(11) 0.0026(11) 0.0053(12) C13A 0.0369(15) 0.0227(14) 0.0287(14) 0.0001(11) 0.0074(11) -0.0056(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 C4 1.360(2) . ? F2 C4 1.362(3) . ? O1 C3 1.312(3) . ? O1 C2 1.458(3) . ? O2 C3 1.205(3) . ? O3 C5 1.419(3) . ? O3 H3 0.8400 . ? C1 C2 1.495(3) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.539(3) . ? C4 C5 1.541(3) . ? C5 C9 1.521(3) . ? C5 C6 1.538(3) . ? C6 C7 1.545(3) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.504(3) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.384(3) . ? C8 C13 1.386(3) . ? C9 C10 1.388(3) . ? C10 C11 1.388(3) . ? C10 H10 0.9500 . ? C11 C12 1.390(3) . ? C11 H11 0.9500 . ? C12 C13 1.383(3) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? F1A C4A 1.357(3) . ? F2A C4A 1.367(3) . ? O1A C3A 1.315(3) . ? O1A C2A 1.466(3) . ? O2A C3A 1.205(3) . ? O3A C5A 1.431(3) . ? O3A H3A 0.8400 . ? C1A C2A 1.492(3) . ? C1A H1A1 0.9800 . ? C1A H1A2 0.9800 . ? C1A H1A3 0.9800 . ? C2A H2A1 0.9900 . ? C2A H2A2 0.9900 . ? C3A C4A 1.536(3) . ? C4A C5A 1.536(3) . ? C5A C9A 1.516(3) . ? C5A C6A 1.543(3) . ? C6A C7A 1.539(3) . ? C6A H6A1 0.9900 . ? C6A H6A2 0.9900 . ? C7A C8A 1.502(3) . ? C7A H7A1 0.9900 . ? C7A H7A2 0.9900 . ? C8A C13A 1.389(3) . ? C8A C9A 1.391(3) . ? C9A C10A 1.385(3) . ? C10A C11A 1.387(3) . ? C10A H10A 0.9500 . ? C11A C12A 1.380(3) . ? C11A H11A 0.9500 . ? C12A C13A 1.385(3) . ? C12A H12A 0.9500 . ? C13A H13A 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 C3 O1 C2 115.23(17) . . ? C5 O3 H3 109.5 . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? O1 C2 C1 107.80(18) . . ? O1 C2 H2A 110.1 . . ? C1 C2 H2A 110.1 . . ? O1 C2 H2B 110.1 . . ? C1 C2 H2B 110.1 . . ? H2A C2 H2B 108.5 . . ? O2 C3 O1 125.3(2) . . ? O2 C3 C4 122.4(2) . . ? O1 C3 C4 112.28(19) . . ? F1 C4 F2 106.37(18) . . ? F1 C4 C3 106.34(18) . . ? F2 C4 C3 109.27(18) . . ? F1 C4 C5 110.17(18) . . ? F2 C4 C5 110.48(18) . . ? C3 C4 C5 113.87(19) . . ? O3 C5 C9 115.88(19) . . ? O3 C5 C6 108.93(18) . . ? C9 C5 C6 102.65(17) . . ? O3 C5 C4 107.18(18) . . ? C9 C5 C4 110.09(18) . . ? C6 C5 C4 112.18(18) . . ? C5 C6 C7 105.91(18) . . ? C5 C6 H6A 110.6 . . ? C7 C6 H6A 110.6 . . ? C5 C6 H6B 110.6 . . ? C7 C6 H6B 110.6 . . ? H6A C6 H6B 108.7 . . ? C8 C7 C6 103.12(18) . . ? C8 C7 H7A 111.1 . . ? C6 C7 H7A 111.1 . . ? C8 C7 H7B 111.1 . . ? C6 C7 H7B 111.1 . . ? H7A C7 H7B 109.1 . . ? C9 C8 C13 120.4(2) . . ? C9 C8 C7 111.1(2) . . ? C13 C8 C7 128.4(2) . . ? C8 C9 C10 121.0(2) . . ? C8 C9 C5 110.53(19) . . ? C10 C9 C5 128.5(2) . . ? C11 C10 C9 118.7(2) . . ? C11 C10 H10 120.6 . . ? C9 C10 H10 120.6 . . ? C10 C11 C12 119.9(2) . . ? C10 C11 H11 120.0 . . ? C12 C11 H11 120.0 . . ? C13 C12 C11 121.4(2) . . ? C13 C12 H12 119.3 . . ? C11 C12 H12 119.3 . . ? C12 C13 C8 118.5(2) . . ? C12 C13 H13 120.7 . . ? C8 C13 H13 120.7 . . ? C3A O1A C2A 115.49(17) . . ? C5A O3A H3A 109.5 . . ? C2A C1A H1A1 109.5 . . ? C2A C1A H1A2 109.5 . . ? H1A1 C1A H1A2 109.5 . . ? C2A C1A H1A3 109.5 . . ? H1A1 C1A H1A3 109.5 . . ? H1A2 C1A H1A3 109.5 . . ? O1A C2A C1A 107.61(18) . . ? O1A C2A H2A1 110.2 . . ? C1A C2A H2A1 110.2 . . ? O1A C2A H2A2 110.2 . . ? C1A C2A H2A2 110.2 . . ? H2A1 C2A H2A2 108.5 . . ? O2A C3A O1A 125.4(2) . . ? O2A C3A C4A 122.7(2) . . ? O1A C3A C4A 111.97(19) . . ? F1A C4A F2A 106.31(18) . . ? F1A C4A C5A 109.79(18) . . ? F2A C4A C5A 110.01(19) . . ? F1A C4A C3A 106.64(18) . . ? F2A C4A C3A 109.55(18) . . ? C5A C4A C3A 114.20(19) . . ? O3A C5A C9A 114.90(18) . . ? O3A C5A C4A 106.53(18) . . ? C9A C5A C4A 111.66(19) . . ? O3A C5A C6A 108.05(18) . . ? C9A C5A C6A 103.45(18) . . ? C4A C5A C6A 112.33(19) . . ? C7A C6A C5A 106.87(18) . . ? C7A C6A H6A1 110.3 . . ? C5A C6A H6A1 110.3 . . ? C7A C6A H6A2 110.3 . . ? C5A C6A H6A2 110.3 . . ? H6A1 C6A H6A2 108.6 . . ? C8A C7A C6A 103.79(18) . . ? C8A C7A H7A1 111.0 . . ? C6A C7A H7A1 111.0 . . ? C8A C7A H7A2 111.0 . . ? C6A C7A H7A2 111.0 . . ? H7A1 C7A H7A2 109.0 . . ? C13A C8A C9A 120.1(2) . . ? C13A C8A C7A 128.5(2) . . ? C9A C8A C7A 111.4(2) . . ? C10A C9A C8A 120.6(2) . . ? C10A C9A C5A 128.6(2) . . ? C8A C9A C5A 110.76(19) . . ? C9A C10A C11A 118.9(2) . . ? C9A C10A H10A 120.6 . . ? C11A C10A H10A 120.6 . . ? C12A C11A C10A 120.6(2) . . ? C12A C11A H11A 119.7 . . ? C10A C11A H11A 119.7 . . ? C11A C12A C13A 120.7(2) . . ? C11A C12A H12A 119.7 . . ? C13A C12A H12A 119.7 . . ? C12A C13A C8A 119.0(2) . . ? C12A C13A H13A 120.5 . . ? C8A C13A H13A 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 C3 O1 C2 C1 174.9(2) . . . . ? C2 O1 C3 O2 -3.5(3) . . . . ? C2 O1 C3 C4 176.14(18) . . . . ? O2 C3 C4 F1 -18.6(3) . . . . ? O1 C3 C4 F1 161.73(18) . . . . ? O2 C3 C4 F2 -133.1(2) . . . . ? O1 C3 C4 F2 47.3(2) . . . . ? O2 C3 C4 C5 102.9(3) . . . . ? O1 C3 C4 C5 -76.8(2) . . . . ? F1 C4 C5 O3 76.8(2) . . . . ? F2 C4 C5 O3 -165.94(17) . . . . ? C3 C4 C5 O3 -42.5(2) . . . . ? F1 C4 C5 C9 -50.0(2) . . . . ? F2 C4 C5 C9 67.2(2) . . . . ? C3 C4 C5 C9 -169.38(18) . . . . ? F1 C4 C5 C6 -163.66(18) . . . . ? F2 C4 C5 C6 -46.4(2) . . . . ? C3 C4 C5 C6 77.0(2) . . . . ? O3 C5 C6 C7 -148.37(18) . . . . ? C9 C5 C6 C7 -25.0(2) . . . . ? C4 C5 C6 C7 93.1(2) . . . . ? C5 C6 C7 C8 24.2(2) . . . . ? C6 C7 C8 C9 -14.2(2) . . . . ? C6 C7 C8 C13 165.7(2) . . . . ? C13 C8 C9 C10 -1.6(3) . . . . ? C7 C8 C9 C10 178.3(2) . . . . ? C13 C8 C9 C5 178.4(2) . . . . ? C7 C8 C9 C5 -1.7(3) . . . . ? O3 C5 C9 C8 135.5(2) . . . . ? C6 C5 C9 C8 16.9(2) . . . . ? C4 C5 C9 C8 -102.7(2) . . . . ? O3 C5 C9 C10 -44.6(3) . . . . ? C6 C5 C9 C10 -163.1(2) . . . . ? C4 C5 C9 C10 77.2(3) . . . . ? C8 C9 C10 C11 0.7(3) . . . . ? C5 C9 C10 C11 -179.2(2) . . . . ? C9 C10 C11 C12 0.7(3) . . . . ? C10 C11 C12 C13 -1.3(4) . . . . ? C11 C12 C13 C8 0.5(4) . . . . ? C9 C8 C13 C12 0.9(3) . . . . ? C7 C8 C13 C12 -178.9(2) . . . . ? C3A O1A C2A C1A 178.83(19) . . . . ? C2A O1A C3A O2A -3.7(3) . . . . ? C2A O1A C3A C4A 174.55(18) . . . . ? O2A C3A C4A F1A -17.3(3) . . . . ? O1A C3A C4A F1A 164.40(17) . . . . ? O2A C3A C4A F2A -132.0(2) . . . . ? O1A C3A C4A F2A 49.8(3) . . . . ? O2A C3A C4A C5A 104.1(3) . . . . ? O1A C3A C4A C5A -74.1(2) . . . . ? F1A C4A C5A O3A 78.1(2) . . . . ? F2A C4A C5A O3A -165.23(16) . . . . ? C3A C4A C5A O3A -41.6(2) . . . . ? F1A C4A C5A C9A -48.1(2) . . . . ? F2A C4A C5A C9A 68.6(2) . . . . ? C3A C4A C5A C9A -167.76(18) . . . . ? F1A C4A C5A C6A -163.76(18) . . . . ? F2A C4A C5A C6A -47.1(2) . . . . ? C3A C4A C5A C6A 76.5(2) . . . . ? O3A C5A C6A C7A -140.79(19) . . . . ? C9A C5A C6A C7A -18.6(2) . . . . ? C4A C5A C6A C7A 102.0(2) . . . . ? C5A C6A C7A C8A 18.7(2) . . . . ? C6A C7A C8A C13A 169.0(2) . . . . ? C6A C7A C8A C9A -12.0(3) . . . . ? C13A C8A C9A C10A -1.1(3) . . . . ? C7A C8A C9A C10A 179.8(2) . . . . ? C13A C8A C9A C5A 179.3(2) . . . . ? C7A C8A C9A C5A 0.2(3) . . . . ? O3A C5A C9A C10A -50.5(3) . . . . ? C4A C5A C9A C10A 71.0(3) . . . . ? C6A C5A C9A C10A -168.0(2) . . . . ? O3A C5A C9A C8A 129.1(2) . . . . ? C4A C5A C9A C8A -109.4(2) . . . . ? C6A C5A C9A C8A 11.6(2) . . . . ? C8A C9A C10A C11A 0.7(3) . . . . ? C5A C9A C10A C11A -179.8(2) . . . . ? C9A C10A C11A C12A -0.5(4) . . . . ? C10A C11A C12A C13A 0.8(4) . . . . ? C11A C12A C13A C8A -1.1(4) . . . . ? C9A C8A C13A C12A 1.3(3) . . . . ? C7A C8A C13A C12A -179.8(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 O3A H3A O2A 0.84 1.98 2.817(2) 172.0 3_766 O3 H3 O2 0.84 2.01 2.837(2) 169.9 3_656 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.321 _refine_diff_density_min -0.215 _refine_diff_density_rms 0.052 # Attachment '08023.cif' data_08023 _database_code_depnum_ccdc_archive 'CCDC 842561' #TrackingRef '08023.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H16 F2 O3' _chemical_formula_sum 'C13 H16 F2 O3' _chemical_formula_weight 258.26 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' 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 10.052(2) _cell_length_b 7.8441(18) _cell_length_c 17.153(4) _cell_angle_alpha 90.00 _cell_angle_beta 106.959(3) _cell_angle_gamma 90.00 _cell_volume 1293.8(5) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 762 _cell_measurement_theta_min 2.754 _cell_measurement_theta_max 24.508 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.326 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 544 _exptl_absorpt_coefficient_mu 0.111 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 2000 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 8916 _diffrn_reflns_av_R_equivalents 0.1658 _diffrn_reflns_av_sigmaI/netI 0.1138 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.12 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2286 _reflns_number_gt 1639 _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^)+(0.0000P)^2^+0.3929P] 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 2286 _refine_ls_number_parameters 166 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0994 _refine_ls_R_factor_gt 0.0622 _refine_ls_wR_factor_ref 0.1463 _refine_ls_wR_factor_gt 0.1330 _refine_ls_goodness_of_fit_ref 1.086 _refine_ls_restrained_S_all 1.086 _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 0.33144(18) 0.5804(2) 0.19604(10) 0.0367(5) Uani 1 1 d . . . F2 F 0.13958(17) 0.5734(2) 0.23020(10) 0.0356(5) Uani 1 1 d . . . O1 O 0.2660(2) 0.4516(2) 0.37314(12) 0.0334(5) Uani 1 1 d . . . O2 O 0.4615(2) 0.4248(3) 0.33520(12) 0.0346(6) Uani 1 1 d . . . O3 O 0.44486(19) 0.8285(3) 0.30524(12) 0.0291(5) Uani 1 1 d . . . H3 H 0.4669 0.8565 0.2634 0.044 Uiso 1 1 calc R . . C1 C 0.2320(5) 0.3479(5) 0.4962(3) 0.0733(14) Uani 1 1 d . . . H1A H 0.2189 0.4665 0.5104 0.110 Uiso 1 1 calc R . . H1B H 0.2736 0.2826 0.5461 0.110 Uiso 1 1 calc R . . H1C H 0.1417 0.2981 0.4671 0.110 Uiso 1 1 calc R . . C2 C 0.3245(4) 0.3425(4) 0.44390(19) 0.0416(9) Uani 1 1 d . . . H2A H 0.4184 0.3832 0.4745 0.050 Uiso 1 1 calc R . . H2B H 0.3327 0.2240 0.4260 0.050 Uiso 1 1 calc R . . C3 C 0.3476(3) 0.4828(4) 0.32687(17) 0.0256(7) Uani 1 1 d . . . C4 C 0.2779(3) 0.6103(4) 0.25898(16) 0.0239(6) Uani 1 1 d . . . C5 C 0.2994(3) 0.8000(4) 0.28425(16) 0.0225(6) Uani 1 1 d . . . C6 C 0.2215(3) 0.9122(4) 0.21200(17) 0.0293(7) Uani 1 1 d . . . H6A H 0.2544 0.8850 0.1644 0.035 Uiso 1 1 calc R . . H6B H 0.1209 0.8858 0.1973 0.035 Uiso 1 1 calc R . . C7 C 0.2429(3) 1.1016(4) 0.2312(2) 0.0402(8) Uani 1 1 d . . . H7A H 0.1998 1.1320 0.2737 0.060 Uiso 1 1 calc R . . H7B H 0.2001 1.1681 0.1819 0.060 Uiso 1 1 calc R . . H7C H 0.3428 1.1265 0.2504 0.060 Uiso 1 1 calc R . . C8 C 0.2532(3) 0.8292(3) 0.36011(16) 0.0211(6) Uani 1 1 d . . . C9 C 0.1133(3) 0.8298(4) 0.35667(18) 0.0284(7) Uani 1 1 d . . . H9 H 0.0445 0.8183 0.3055 0.034 Uiso 1 1 calc R . . C10 C 0.0736(3) 0.8470(4) 0.4263(2) 0.0339(8) Uani 1 1 d . . . H10 H -0.0225 0.8472 0.4227 0.041 Uiso 1 1 calc R . . C11 C 0.1712(3) 0.8638(4) 0.50147(18) 0.0319(8) Uani 1 1 d . . . H11 H 0.1431 0.8733 0.5496 0.038 Uiso 1 1 calc R . . C12 C 0.3106(3) 0.8667(4) 0.50570(18) 0.0308(7) Uani 1 1 d . . . H12 H 0.3789 0.8797 0.5570 0.037 Uiso 1 1 calc R . . C13 C 0.3512(3) 0.8507(3) 0.43551(17) 0.0246(7) Uani 1 1 d . . . H13 H 0.4472 0.8545 0.4390 0.030 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 0.0502(12) 0.0392(11) 0.0256(9) -0.0007(8) 0.0188(9) 0.0098(8) F2 0.0288(10) 0.0351(10) 0.0374(10) -0.0051(8) 0.0011(8) -0.0051(8) O1 0.0404(13) 0.0291(11) 0.0376(13) 0.0075(10) 0.0221(11) 0.0070(9) O2 0.0306(13) 0.0410(13) 0.0352(13) 0.0076(10) 0.0145(10) 0.0090(10) O3 0.0199(11) 0.0420(13) 0.0275(11) 0.0035(10) 0.0102(9) -0.0039(9) C1 0.113(4) 0.062(3) 0.071(3) 0.027(2) 0.068(3) 0.024(3) C2 0.063(2) 0.0354(19) 0.0310(19) 0.0146(15) 0.0217(17) 0.0079(17) C3 0.0332(18) 0.0211(16) 0.0249(16) -0.0028(12) 0.0122(14) -0.0016(13) C4 0.0204(15) 0.0314(16) 0.0217(15) -0.0036(12) 0.0089(12) 0.0009(12) C5 0.0156(15) 0.0288(16) 0.0238(15) 0.0001(12) 0.0069(12) -0.0027(12) C6 0.0282(17) 0.0348(17) 0.0250(16) 0.0062(13) 0.0078(13) 0.0012(13) C7 0.046(2) 0.0304(18) 0.042(2) 0.0097(15) 0.0098(17) 0.0078(15) C8 0.0220(15) 0.0177(14) 0.0228(15) 0.0005(12) 0.0055(12) 0.0014(11) C9 0.0260(17) 0.0327(17) 0.0268(16) -0.0004(13) 0.0080(13) 0.0058(13) C10 0.0271(17) 0.0392(19) 0.0397(19) 0.0008(15) 0.0166(15) 0.0052(14) C11 0.0374(19) 0.0379(18) 0.0247(17) 0.0016(14) 0.0157(15) 0.0070(14) C12 0.0345(18) 0.0330(18) 0.0208(16) 0.0008(13) 0.0016(14) -0.0010(14) C13 0.0237(16) 0.0274(16) 0.0226(15) 0.0028(12) 0.0066(13) 0.0008(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 C4 1.360(3) . ? F2 C4 1.364(3) . ? O1 C3 1.320(3) . ? O1 C2 1.461(4) . ? O2 C3 1.201(3) . ? O3 C5 1.417(3) . ? O3 H3 0.8400 . ? C1 C2 1.469(4) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.540(4) . ? C4 C5 1.547(4) . ? C5 C8 1.522(4) . ? C5 C6 1.536(4) . ? C6 C7 1.524(4) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 C13 1.389(4) . ? C8 C9 1.390(4) . ? C9 C10 1.372(4) . ? C9 H9 0.9500 . ? C10 C11 1.380(4) . ? C10 H10 0.9500 . ? C11 C12 1.382(4) . ? C11 H11 0.9500 . ? C12 C13 1.385(4) . ? C12 H12 0.9500 . ? C13 H13 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 C3 O1 C2 116.0(2) . . ? C5 O3 H3 109.5 . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? O1 C2 C1 108.5(3) . . ? O1 C2 H2A 110.0 . . ? C1 C2 H2A 110.0 . . ? O1 C2 H2B 110.0 . . ? C1 C2 H2B 110.0 . . ? H2A C2 H2B 108.4 . . ? O2 C3 O1 126.6(3) . . ? O2 C3 C4 122.9(2) . . ? O1 C3 C4 110.5(2) . . ? F1 C4 F2 105.9(2) . . ? F1 C4 C3 106.9(2) . . ? F2 C4 C3 109.1(2) . . ? F1 C4 C5 109.4(2) . . ? F2 C4 C5 110.5(2) . . ? C3 C4 C5 114.6(2) . . ? O3 C5 C8 108.0(2) . . ? O3 C5 C6 111.1(2) . . ? C8 C5 C6 113.1(2) . . ? O3 C5 C4 105.8(2) . . ? C8 C5 C4 109.4(2) . . ? C6 C5 C4 109.2(2) . . ? C7 C6 C5 112.2(2) . . ? C7 C6 H6A 109.2 . . ? C5 C6 H6A 109.2 . . ? C7 C6 H6B 109.2 . . ? C5 C6 H6B 109.2 . . ? H6A C6 H6B 107.9 . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C13 C8 C9 118.2(2) . . ? C13 C8 C5 120.3(2) . . ? C9 C8 C5 121.5(2) . . ? C10 C9 C8 120.7(3) . . ? C10 C9 H9 119.6 . . ? C8 C9 H9 119.6 . . ? C9 C10 C11 120.9(3) . . ? C9 C10 H10 119.5 . . ? C11 C10 H10 119.5 . . ? C10 C11 C12 119.0(3) . . ? C10 C11 H11 120.5 . . ? C12 C11 H11 120.5 . . ? C11 C12 C13 120.3(3) . . ? C11 C12 H12 119.9 . . ? C13 C12 H12 119.9 . . ? C12 C13 C8 120.8(3) . . ? C12 C13 H13 119.6 . . ? C8 C13 H13 119.6 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C3 O1 C2 C1 169.4(3) . . . . ? C2 O1 C3 O2 3.5(4) . . . . ? C2 O1 C3 C4 -175.4(2) . . . . ? O2 C3 C4 F1 27.4(4) . . . . ? O1 C3 C4 F1 -153.6(2) . . . . ? O2 C3 C4 F2 141.5(3) . . . . ? O1 C3 C4 F2 -39.5(3) . . . . ? O2 C3 C4 C5 -94.0(3) . . . . ? O1 C3 C4 C5 84.9(3) . . . . ? F1 C4 C5 O3 -58.1(3) . . . . ? F2 C4 C5 O3 -174.32(19) . . . . ? C3 C4 C5 O3 62.0(3) . . . . ? F1 C4 C5 C8 -174.2(2) . . . . ? F2 C4 C5 C8 69.6(3) . . . . ? C3 C4 C5 C8 -54.1(3) . . . . ? F1 C4 C5 C6 61.5(3) . . . . ? F2 C4 C5 C6 -54.7(3) . . . . ? C3 C4 C5 C6 -178.4(2) . . . . ? O3 C5 C6 C7 -61.3(3) . . . . ? C8 C5 C6 C7 60.3(3) . . . . ? C4 C5 C6 C7 -177.6(2) . . . . ? O3 C5 C8 C13 -9.5(3) . . . . ? C6 C5 C8 C13 -132.9(3) . . . . ? C4 C5 C8 C13 105.2(3) . . . . ? O3 C5 C8 C9 172.6(2) . . . . ? C6 C5 C8 C9 49.2(3) . . . . ? C4 C5 C8 C9 -72.7(3) . . . . ? C13 C8 C9 C10 -1.6(4) . . . . ? C5 C8 C9 C10 176.4(3) . . . . ? C8 C9 C10 C11 -0.1(4) . . . . ? C9 C10 C11 C12 1.3(4) . . . . ? C10 C11 C12 C13 -0.8(4) . . . . ? C11 C12 C13 C8 -0.9(4) . . . . ? C9 C8 C13 C12 2.1(4) . . . . ? C5 C8 C13 C12 -175.9(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 O3 H3 O2 0.84 2.09 2.930(3) 175.4 2_655 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.270 _refine_diff_density_min -0.199 _refine_diff_density_rms 0.051 # Attachment '09044.cif' data_09044 _database_code_depnum_ccdc_archive 'CCDC 842562' #TrackingRef '09044.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H18 F2 O3' _chemical_formula_sum 'C14 H18 F2 O3' _chemical_formula_weight 272.28 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' 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 Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 7.046(3) _cell_length_b 16.235(7) _cell_length_c 24.642(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2819(2) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 946 _cell_measurement_theta_min 2.642 _cell_measurement_theta_max 24.409 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.283 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1152 _exptl_absorpt_coefficient_mu 0.106 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9679 _exptl_absorpt_correction_T_max 0.9822 _exptl_absorpt_process_details ; absorption correction based on 6170 reflections(SADABS);Rint 0.1869 before correction and 0.0572 after. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 2000 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 18732 _diffrn_reflns_av_R_equivalents 0.0929 _diffrn_reflns_av_sigmaI/netI 0.0457 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 2.51 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2484 _reflns_number_gt 1929 _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^)+(0.0510P)^2^+0.6594P] 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 2484 _refine_ls_number_parameters 175 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0712 _refine_ls_R_factor_gt 0.0498 _refine_ls_wR_factor_ref 0.1184 _refine_ls_wR_factor_gt 0.1087 _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_restrained_S_all 1.042 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group F1 F 0.33417(18) 1.06160(6) 0.44867(4) 0.0361(3) Uani 1 1 d . . . F2 F 0.13691(17) 1.01844(7) 0.38734(4) 0.0342(3) Uani 1 1 d . . . O1 O 0.0655(2) 0.88356(8) 0.44450(5) 0.0335(4) Uani 1 1 d . . . O2 O 0.1963(2) 0.95034(9) 0.51519(5) 0.0360(4) Uani 1 1 d . . . O3 O 0.5591(2) 0.92391(8) 0.43760(5) 0.0337(4) Uani 1 1 d . . . H3 H 0.6173 0.9647 0.4504 0.051 Uiso 1 1 calc R . . C1 C -0.0403(4) 0.74558(14) 0.44928(12) 0.0606(8) Uani 1 1 d . . . H1A H -0.1155 0.7537 0.4163 0.091 Uiso 1 1 calc R . . H1B H -0.1008 0.7036 0.4720 0.091 Uiso 1 1 calc R . . H1C H 0.0878 0.7274 0.4394 0.091 Uiso 1 1 calc R . . C2 C -0.0290(3) 0.82353(13) 0.47940(10) 0.0411(6) Uani 1 1 d . . . H2A H -0.1579 0.8430 0.4890 0.049 Uiso 1 1 calc R . . H2B H 0.0441 0.8158 0.5133 0.049 Uiso 1 1 calc R . . C3 C 0.1723(3) 0.94004(12) 0.46724(8) 0.0282(5) Uani 1 1 d . . . C4 C 0.2693(3) 0.99201(11) 0.42353(8) 0.0265(5) Uani 1 1 d . . . C5 C 0.4374(3) 0.95032(11) 0.39509(7) 0.0260(5) Uani 1 1 d . . . C6 C 0.5381(3) 1.01166(12) 0.35767(8) 0.0309(5) Uani 1 1 d . . . H6A H 0.4460 1.0319 0.3304 0.037 Uiso 1 1 calc R . . H6B H 0.5800 1.0595 0.3795 0.037 Uiso 1 1 calc R . . C7 C 0.7081(3) 0.97621(14) 0.32841(9) 0.0409(6) Uani 1 1 d . . . H7A H 0.6661 0.9302 0.3050 0.049 Uiso 1 1 calc R . . H7B H 0.7985 0.9538 0.3554 0.049 Uiso 1 1 calc R . . C8 C 0.8080(3) 1.04013(17) 0.29394(9) 0.0512(7) Uani 1 1 d . . . H8A H 0.7190 1.0624 0.2671 0.077 Uiso 1 1 calc R . . H8B H 0.9156 1.0146 0.2752 0.077 Uiso 1 1 calc R . . H8C H 0.8540 1.0848 0.3172 0.077 Uiso 1 1 calc R . . C9 C 0.3729(3) 0.87340(12) 0.36459(8) 0.0284(5) Uani 1 1 d . . . C10 C 0.4358(4) 0.79649(13) 0.37990(9) 0.0429(6) Uani 1 1 d . . . H10 H 0.5215 0.7910 0.4095 0.051 Uiso 1 1 calc R . . C11 C 0.3745(5) 0.72708(15) 0.35229(13) 0.0641(9) Uani 1 1 d . . . H11 H 0.4178 0.6743 0.3634 0.077 Uiso 1 1 calc R . . C12 C 0.2528(5) 0.73351(17) 0.30938(12) 0.0720(10) Uani 1 1 d . . . H12 H 0.2113 0.6855 0.2908 0.086 Uiso 1 1 calc R . . C13 C 0.1915(4) 0.80934(17) 0.29345(10) 0.0589(8) Uani 1 1 d . . . H13 H 0.1072 0.8142 0.2635 0.071 Uiso 1 1 calc R . . C14 C 0.2514(3) 0.87945(14) 0.32062(8) 0.0405(6) Uani 1 1 d . . . H14 H 0.2087 0.9321 0.3090 0.049 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 F1 0.0478(8) 0.0257(6) 0.0347(7) -0.0051(5) 0.0011(6) -0.0051(5) F2 0.0343(7) 0.0323(7) 0.0361(7) 0.0067(5) -0.0067(6) 0.0061(5) O1 0.0383(9) 0.0289(8) 0.0333(8) 0.0013(6) 0.0043(7) -0.0051(7) O2 0.0351(9) 0.0461(9) 0.0270(8) 0.0017(7) -0.0001(7) -0.0004(7) O3 0.0313(9) 0.0407(9) 0.0292(8) 0.0067(6) -0.0067(6) 0.0014(7) C1 0.0608(19) 0.0307(13) 0.090(2) -0.0002(13) 0.0298(16) -0.0100(12) C2 0.0382(14) 0.0364(12) 0.0487(14) 0.0103(11) 0.0119(11) -0.0062(11) C3 0.0235(11) 0.0261(10) 0.0351(12) -0.0012(9) 0.0002(9) 0.0052(9) C4 0.0310(12) 0.0206(10) 0.0280(11) -0.0016(8) -0.0077(9) -0.0010(9) C5 0.0271(11) 0.0262(10) 0.0248(10) 0.0023(8) -0.0027(9) -0.0009(9) C6 0.0359(13) 0.0303(11) 0.0264(10) 0.0020(9) -0.0048(9) -0.0096(9) C7 0.0342(13) 0.0522(14) 0.0362(12) 0.0082(11) 0.0025(11) -0.0060(11) C8 0.0387(15) 0.0753(18) 0.0396(13) 0.0135(12) -0.0031(12) -0.0190(13) C9 0.0279(11) 0.0289(11) 0.0283(10) -0.0024(9) 0.0088(9) -0.0014(9) C10 0.0530(15) 0.0298(12) 0.0458(14) 0.0023(10) 0.0210(12) 0.0054(11) C11 0.093(2) 0.0242(13) 0.075(2) -0.0064(13) 0.0420(19) -0.0007(13) C12 0.109(3) 0.0450(17) 0.0624(19) -0.0281(15) 0.0353(19) -0.0366(17) C13 0.071(2) 0.0624(18) 0.0436(15) -0.0170(13) 0.0063(14) -0.0326(15) C14 0.0464(14) 0.0390(13) 0.0360(12) -0.0039(10) 0.0021(11) -0.0125(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 C4 1.367(2) . ? F2 C4 1.360(2) . ? O1 C3 1.312(2) . ? O1 C2 1.460(2) . ? O2 C3 1.205(2) . ? O3 C5 1.420(2) . ? O3 H3 0.8400 . ? C1 C2 1.469(3) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.529(3) . ? C4 C5 1.534(3) . ? C5 C9 1.527(3) . ? C5 C6 1.531(3) . ? C6 C7 1.512(3) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.515(3) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 C10 1.378(3) . ? C9 C14 1.385(3) . ? C10 C11 1.385(4) . ? C10 H10 0.9500 . ? C11 C12 1.365(4) . ? C11 H11 0.9500 . ? C12 C13 1.363(4) . ? C12 H12 0.9500 . ? C13 C14 1.386(3) . ? C13 H13 0.9500 . ? C14 H14 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 C3 O1 C2 118.45(16) . . ? C5 O3 H3 109.5 . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? O1 C2 C1 107.58(19) . . ? O1 C2 H2A 110.2 . . ? C1 C2 H2A 110.2 . . ? O1 C2 H2B 110.2 . . ? C1 C2 H2B 110.2 . . ? H2A C2 H2B 108.5 . . ? O2 C3 O1 126.60(19) . . ? O2 C3 C4 123.44(18) . . ? O1 C3 C4 109.95(17) . . ? F2 C4 F1 105.40(14) . . ? F2 C4 C3 109.22(16) . . ? F1 C4 C3 106.64(15) . . ? F2 C4 C5 111.67(15) . . ? F1 C4 C5 108.27(16) . . ? C3 C4 C5 115.07(15) . . ? O3 C5 C9 107.22(15) . . ? O3 C5 C6 111.17(16) . . ? C9 C5 C6 111.92(16) . . ? O3 C5 C4 105.20(15) . . ? C9 C5 C4 110.85(16) . . ? C6 C5 C4 110.23(16) . . ? C7 C6 C5 113.98(17) . . ? C7 C6 H6A 108.8 . . ? C5 C6 H6A 108.8 . . ? C7 C6 H6B 108.8 . . ? C5 C6 H6B 108.8 . . ? H6A C6 H6B 107.7 . . ? C6 C7 C8 112.0(2) . . ? C6 C7 H7A 109.2 . . ? C8 C7 H7A 109.2 . . ? C6 C7 H7B 109.2 . . ? C8 C7 H7B 109.2 . . ? H7A C7 H7B 107.9 . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C10 C9 C14 118.5(2) . . ? C10 C9 C5 120.7(2) . . ? C14 C9 C5 120.76(18) . . ? C9 C10 C11 120.2(3) . . ? C9 C10 H10 119.9 . . ? C11 C10 H10 119.9 . . ? C12 C11 C10 120.9(3) . . ? C12 C11 H11 119.5 . . ? C10 C11 H11 119.5 . . ? C13 C12 C11 119.4(2) . . ? C13 C12 H12 120.3 . . ? C11 C12 H12 120.3 . . ? C12 C13 C14 120.4(3) . . ? C12 C13 H13 119.8 . . ? C14 C13 H13 119.8 . . ? C9 C14 C13 120.5(2) . . ? C9 C14 H14 119.7 . . ? C13 C14 H14 119.7 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C3 O1 C2 C1 -147.3(2) . . . . ? C2 O1 C3 O2 -3.1(3) . . . . ? C2 O1 C3 C4 175.63(16) . . . . ? O2 C3 C4 F2 -130.72(19) . . . . ? O1 C3 C4 F2 50.46(19) . . . . ? O2 C3 C4 F1 -17.3(3) . . . . ? O1 C3 C4 F1 163.89(15) . . . . ? O2 C3 C4 C5 102.8(2) . . . . ? O1 C3 C4 C5 -76.0(2) . . . . ? F2 C4 C5 O3 -178.12(14) . . . . ? F1 C4 C5 O3 66.27(17) . . . . ? C3 C4 C5 O3 -52.9(2) . . . . ? F2 C4 C5 C9 -62.55(19) . . . . ? F1 C4 C5 C9 -178.15(14) . . . . ? C3 C4 C5 C9 62.7(2) . . . . ? F2 C4 C5 C6 61.9(2) . . . . ? F1 C4 C5 C6 -53.67(19) . . . . ? C3 C4 C5 C6 -172.83(16) . . . . ? O3 C5 C6 C7 62.9(2) . . . . ? C9 C5 C6 C7 -57.0(2) . . . . ? C4 C5 C6 C7 179.17(16) . . . . ? C5 C6 C7 C8 -177.39(17) . . . . ? O3 C5 C9 C10 -0.8(3) . . . . ? C6 C5 C9 C10 121.3(2) . . . . ? C4 C5 C9 C10 -115.2(2) . . . . ? O3 C5 C9 C14 179.78(18) . . . . ? C6 C5 C9 C14 -58.1(3) . . . . ? C4 C5 C9 C14 65.5(2) . . . . ? C14 C9 C10 C11 -1.4(3) . . . . ? C5 C9 C10 C11 179.2(2) . . . . ? C9 C10 C11 C12 0.6(4) . . . . ? C10 C11 C12 C13 0.2(4) . . . . ? C11 C12 C13 C14 -0.2(4) . . . . ? C10 C9 C14 C13 1.3(3) . . . . ? C5 C9 C14 C13 -179.3(2) . . . . ? C12 C13 C14 C9 -0.6(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 O3 H3 O2 0.84 2.09 2.914(2) 168.9 5_676 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.211 _refine_diff_density_min -0.184 _refine_diff_density_rms 0.044 # Attachment '09048.cif' data_09048 _database_code_depnum_ccdc_archive 'CCDC 842563' #TrackingRef '09048.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H20 F2 O3' _chemical_formula_sum 'C15 H20 F2 O3' _chemical_formula_weight 286.31 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' 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 7.953(3) _cell_length_b 20.190(8) _cell_length_c 9.179(4) _cell_angle_alpha 90.00 _cell_angle_beta 93.291(9) _cell_angle_gamma 90.00 _cell_volume 1471.4(10) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 408 _cell_measurement_theta_min 2.441 _cell_measurement_theta_max 23.311 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.292 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 608 _exptl_absorpt_coefficient_mu 0.105 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9783 _exptl_absorpt_correction_T_max 0.9948 _exptl_absorpt_process_details ; absorption correction based on 922 reflections(SADABS);Rint 0.2165 before correction and 0.1143 after. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 2000 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 10577 _diffrn_reflns_av_R_equivalents 0.4355 _diffrn_reflns_av_sigmaI/netI 0.3068 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.02 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2591 _reflns_number_gt 996 _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^)+(0.0000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2591 _refine_ls_number_parameters 185 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2035 _refine_ls_R_factor_gt 0.0886 _refine_ls_wR_factor_ref 0.1847 _refine_ls_wR_factor_gt 0.1417 _refine_ls_goodness_of_fit_ref 0.846 _refine_ls_restrained_S_all 0.846 _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 0.3588(4) 0.42052(14) -0.0694(4) 0.0388(10) Uani 1 1 d . . . F2 F 0.1813(4) 0.36309(13) 0.0486(4) 0.0358(10) Uani 1 1 d . . . O1 O 0.1069(5) 0.46715(16) 0.2046(5) 0.0328(11) Uani 1 1 d . . . O2 O 0.2383(5) 0.52822(17) 0.0435(5) 0.0379(12) Uani 1 1 d . . . O3 O 0.5476(5) 0.44930(17) 0.1871(4) 0.0335(11) Uani 1 1 d . . . H3 H 0.5979 0.4546 0.1100 0.050 Uiso 1 1 calc R . . C1 C 0.1253(8) 0.5569(3) 0.3820(7) 0.0439(19) Uani 1 1 d . . . H1A H 0.1514 0.5236 0.4577 0.066 Uiso 1 1 calc R . . H1B H 0.0638 0.5937 0.4238 0.066 Uiso 1 1 calc R . . H1C H 0.2302 0.5735 0.3444 0.066 Uiso 1 1 calc R . . C2 C 0.0187(8) 0.5261(2) 0.2598(7) 0.0384(17) Uani 1 1 d . . . H2A H -0.0916 0.5128 0.2952 0.046 Uiso 1 1 calc R . . H2B H -0.0016 0.5587 0.1800 0.046 Uiso 1 1 calc R . . C3 C 0.2127(7) 0.4763(3) 0.1031(7) 0.0266(15) Uani 1 1 d . . . C4 C 0.2978(7) 0.4115(3) 0.0650(7) 0.0282(15) Uani 1 1 d . . . C5 C 0.4451(8) 0.3910(2) 0.1745(7) 0.0323(17) Uani 1 1 d . . . C6 C 0.5385(7) 0.3329(2) 0.1075(7) 0.0319(16) Uani 1 1 d . . . H6A H 0.4545 0.2991 0.0746 0.038 Uiso 1 1 calc R . . H6B H 0.5929 0.3492 0.0199 0.038 Uiso 1 1 calc R . . C7 C 0.6726(7) 0.2996(3) 0.2085(7) 0.0366(17) Uani 1 1 d . . . H7 H 0.6155 0.2829 0.2955 0.044 Uiso 1 1 calc R . . C8 C 0.7444(8) 0.2396(3) 0.1314(8) 0.058(2) Uani 1 1 d . . . H8A H 0.8120 0.2547 0.0518 0.086 Uiso 1 1 calc R . . H8B H 0.6518 0.2118 0.0916 0.086 Uiso 1 1 calc R . . H8C H 0.8155 0.2139 0.2013 0.086 Uiso 1 1 calc R . . C9 C 0.8116(8) 0.3451(3) 0.2631(8) 0.052(2) Uani 1 1 d . . . H9A H 0.8704 0.3624 0.1801 0.079 Uiso 1 1 calc R . . H9B H 0.8913 0.3206 0.3282 0.079 Uiso 1 1 calc R . . H9C H 0.7640 0.3820 0.3165 0.079 Uiso 1 1 calc R . . C10 C 0.3841(7) 0.3759(2) 0.3240(7) 0.0267(15) Uani 1 1 d . . . C11 C 0.4312(7) 0.4148(2) 0.4417(6) 0.0249(15) Uani 1 1 d . . . H11 H 0.5010 0.4522 0.4280 0.030 Uiso 1 1 calc R . . C12 C 0.3805(8) 0.4013(2) 0.5780(8) 0.0382(18) Uani 1 1 d . . . H12 H 0.4149 0.4293 0.6574 0.046 Uiso 1 1 calc R . . C13 C 0.2778(7) 0.3462(2) 0.6016(7) 0.0336(16) Uani 1 1 d . . . H13 H 0.2411 0.3366 0.6959 0.040 Uiso 1 1 calc R . . C14 C 0.2315(7) 0.3062(3) 0.4829(7) 0.0327(16) Uani 1 1 d . . . H14 H 0.1624 0.2685 0.4959 0.039 Uiso 1 1 calc R . . C15 C 0.2851(7) 0.3207(2) 0.3465(7) 0.0323(17) Uani 1 1 d . . . H15 H 0.2537 0.2926 0.2666 0.039 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 0.053(3) 0.0275(19) 0.036(2) -0.0013(17) 0.003(2) 0.0063(16) F2 0.042(2) 0.0118(16) 0.052(2) -0.0045(16) -0.0108(19) -0.0023(15) O1 0.031(3) 0.014(2) 0.053(3) -0.004(2) 0.000(2) 0.0011(18) O2 0.050(3) 0.017(2) 0.048(3) 0.012(2) 0.007(2) 0.0035(19) O3 0.038(3) 0.016(2) 0.046(3) -0.006(2) -0.002(2) -0.0081(18) C1 0.045(5) 0.031(3) 0.056(5) -0.014(3) -0.002(4) 0.006(3) C2 0.041(4) 0.021(3) 0.052(5) -0.002(3) -0.001(4) 0.007(3) C3 0.018(3) 0.019(3) 0.042(4) -0.007(3) -0.004(3) 0.002(3) C4 0.032(4) 0.016(3) 0.038(4) -0.007(3) 0.010(3) -0.001(3) C5 0.039(4) 0.012(3) 0.045(4) -0.002(3) -0.008(4) -0.004(3) C6 0.034(4) 0.016(3) 0.047(4) -0.007(3) 0.000(3) -0.006(3) C7 0.038(4) 0.021(3) 0.051(5) 0.004(3) 0.000(3) 0.006(3) C8 0.062(6) 0.029(4) 0.079(6) -0.015(4) -0.016(5) 0.024(3) C9 0.047(5) 0.039(4) 0.069(6) 0.000(4) -0.016(4) -0.005(3) C10 0.030(4) 0.012(3) 0.038(4) 0.001(3) 0.000(3) 0.010(2) C11 0.031(4) 0.015(3) 0.029(4) 0.000(3) 0.000(3) -0.004(3) C12 0.052(5) 0.013(3) 0.049(5) -0.002(3) -0.007(4) -0.004(3) C13 0.040(4) 0.022(3) 0.040(4) 0.010(3) 0.010(3) 0.007(3) C14 0.035(4) 0.017(3) 0.046(5) 0.005(3) -0.001(3) 0.003(3) C15 0.040(4) 0.012(3) 0.043(4) -0.003(3) -0.010(3) 0.001(3) _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 C4 1.364(7) . ? F2 C4 1.349(6) . ? O1 C3 1.304(7) . ? O1 C2 1.486(6) . ? O2 C3 1.205(6) . ? O3 C5 1.432(6) . ? O3 H3 0.8400 . ? C1 C2 1.502(7) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.522(7) . ? C4 C5 1.555(7) . ? C5 C10 1.512(8) . ? C5 C6 1.536(7) . ? C6 C7 1.528(7) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C9 1.501(7) . ? C7 C8 1.531(8) . ? C7 H7 1.0000 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 C11 1.371(7) . ? C10 C15 1.387(7) . ? C11 C12 1.364(8) . ? C11 H11 0.9500 . ? C12 C13 1.404(7) . ? C12 H12 0.9500 . ? C13 C14 1.389(7) . ? C13 H13 0.9500 . ? C14 C15 1.378(8) . ? C14 H14 0.9500 . ? C15 H15 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 C3 O1 C2 117.9(4) . . ? C5 O3 H3 109.5 . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? O1 C2 C1 109.2(5) . . ? O1 C2 H2A 109.8 . . ? C1 C2 H2A 109.8 . . ? O1 C2 H2B 109.8 . . ? C1 C2 H2B 109.8 . . ? H2A C2 H2B 108.3 . . ? O2 C3 O1 125.4(5) . . ? O2 C3 C4 123.7(6) . . ? O1 C3 C4 110.9(5) . . ? F2 C4 F1 105.8(5) . . ? F2 C4 C3 109.7(5) . . ? F1 C4 C3 106.2(5) . . ? F2 C4 C5 111.5(4) . . ? F1 C4 C5 109.0(5) . . ? C3 C4 C5 114.1(5) . . ? O3 C5 C10 107.7(5) . . ? O3 C5 C6 111.9(5) . . ? C10 C5 C6 113.4(5) . . ? O3 C5 C4 103.8(4) . . ? C10 C5 C4 111.8(5) . . ? C6 C5 C4 107.9(5) . . ? C7 C6 C5 115.4(5) . . ? C7 C6 H6A 108.4 . . ? C5 C6 H6A 108.4 . . ? C7 C6 H6B 108.4 . . ? C5 C6 H6B 108.4 . . ? H6A C6 H6B 107.5 . . ? C9 C7 C6 114.1(5) . . ? C9 C7 C8 110.5(5) . . ? C6 C7 C8 109.5(5) . . ? C9 C7 H7 107.5 . . ? C6 C7 H7 107.5 . . ? C8 C7 H7 107.5 . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C7 C9 H9A 109.5 . . ? C7 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C7 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C11 C10 C15 118.4(6) . . ? C11 C10 C5 120.8(5) . . ? C15 C10 C5 120.8(5) . . ? C12 C11 C10 121.8(5) . . ? C12 C11 H11 119.1 . . ? C10 C11 H11 119.1 . . ? C11 C12 C13 120.3(6) . . ? C11 C12 H12 119.8 . . ? C13 C12 H12 119.8 . . ? C14 C13 C12 118.1(6) . . ? C14 C13 H13 120.9 . . ? C12 C13 H13 120.9 . . ? C15 C14 C13 120.4(5) . . ? C15 C14 H14 119.8 . . ? C13 C14 H14 119.8 . . ? C14 C15 C10 121.0(6) . . ? C14 C15 H15 119.5 . . ? C10 C15 H15 119.5 . . ? 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 C3 O1 C2 C1 -87.4(6) . . . . ? C2 O1 C3 O2 -4.6(8) . . . . ? C2 O1 C3 C4 177.2(4) . . . . ? O2 C3 C4 F2 -132.1(5) . . . . ? O1 C3 C4 F2 46.2(6) . . . . ? O2 C3 C4 F1 -18.2(7) . . . . ? O1 C3 C4 F1 160.1(4) . . . . ? O2 C3 C4 C5 101.9(7) . . . . ? O1 C3 C4 C5 -79.8(6) . . . . ? F2 C4 C5 O3 -175.5(5) . . . . ? F1 C4 C5 O3 68.0(5) . . . . ? C3 C4 C5 O3 -50.6(7) . . . . ? F2 C4 C5 C10 -59.8(6) . . . . ? F1 C4 C5 C10 -176.3(4) . . . . ? C3 C4 C5 C10 65.2(6) . . . . ? F2 C4 C5 C6 65.5(6) . . . . ? F1 C4 C5 C6 -51.0(6) . . . . ? C3 C4 C5 C6 -169.5(5) . . . . ? O3 C5 C6 C7 74.6(7) . . . . ? C10 C5 C6 C7 -47.4(7) . . . . ? C4 C5 C6 C7 -171.8(5) . . . . ? C5 C6 C7 C9 -60.0(8) . . . . ? C5 C6 C7 C8 175.5(5) . . . . ? O3 C5 C10 C11 -1.0(7) . . . . ? C6 C5 C10 C11 123.4(5) . . . . ? C4 C5 C10 C11 -114.3(6) . . . . ? O3 C5 C10 C15 -178.3(5) . . . . ? C6 C5 C10 C15 -53.9(7) . . . . ? C4 C5 C10 C15 68.4(6) . . . . ? C15 C10 C11 C12 -1.3(9) . . . . ? C5 C10 C11 C12 -178.6(5) . . . . ? C10 C11 C12 C13 0.2(9) . . . . ? C11 C12 C13 C14 0.6(9) . . . . ? C12 C13 C14 C15 -0.2(8) . . . . ? C13 C14 C15 C10 -0.8(9) . . . . ? C11 C10 C15 C14 1.6(8) . . . . ? C5 C10 C15 C14 178.9(5) . . . . ? 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 O3 H3 O2 0.84 2.00 2.829(6) 167.3 3_665 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.364 _refine_diff_density_min -0.299 _refine_diff_density_rms 0.081 # Attachment '09082.cif' data_09082 _database_code_depnum_ccdc_archive 'CCDC 842564' #TrackingRef '09082.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H19 F2 N O2' _chemical_formula_sum 'C18 H19 F2 N O2' _chemical_formula_weight 319.34 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 8.402(3) _cell_length_b 9.710(4) _cell_length_c 19.088(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1557.3(10) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 587 _cell_measurement_theta_min 2.353 _cell_measurement_theta_max 20.048 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.362 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 672 _exptl_absorpt_coefficient_mu 0.104 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.569 _exptl_absorpt_correction_T_max 0.969 _exptl_absorpt_process_details ; absorption correction based on 587 reflections(SADABS);Rint 0.1898 before correction and 0.0707 after. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 2000 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 11336 _diffrn_reflns_av_R_equivalents 0.1280 _diffrn_reflns_av_sigmaI/netI 0.0994 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.13 _diffrn_reflns_theta_max 24.99 _reflns_number_total 2739 _reflns_number_gt 2098 _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^)+(0.0251P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -1.5(9) _chemical_absolute_configuration ,unk _refine_ls_number_reflns 2739 _refine_ls_number_parameters 211 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0692 _refine_ls_R_factor_gt 0.0512 _refine_ls_wR_factor_ref 0.0919 _refine_ls_wR_factor_gt 0.0862 _refine_ls_goodness_of_fit_ref 0.912 _refine_ls_restrained_S_all 0.912 _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 1.11937(17) 0.07738(18) 0.89680(8) 0.0343(5) Uani 1 1 d . . . F2 F 1.02251(17) 0.27292(16) 0.86078(8) 0.0281(4) Uani 1 1 d . . . O1 O 0.8302(3) -0.02614(19) 0.93189(10) 0.0313(5) Uani 1 1 d . . . H1 H 0.8480 -0.0729 0.8957 0.047 Uiso 1 1 calc R . . O2 O 0.9503(2) -0.0545(2) 0.79121(11) 0.0312(5) Uani 1 1 d . . . N1 N 0.9537(3) 0.1572(2) 0.74118(11) 0.0233(6) Uani 1 1 d . . . H1A H 0.9749 0.2449 0.7482 0.028 Uiso 1 1 calc R . . C1 C 0.8429(3) 0.1158(3) 0.91569(14) 0.0246(7) Uani 1 1 d . . . C2 C 0.9880(3) 0.1355(3) 0.86714(15) 0.0241(7) Uani 1 1 d . . . C3 C 0.9651(3) 0.0717(3) 0.79471(15) 0.0230(7) Uani 1 1 d . . . C4 C 0.9080(3) 0.1138(3) 0.67118(14) 0.0247(7) Uani 1 1 d . . . H4 H 0.8718 0.0158 0.6740 0.030 Uiso 1 1 calc R . . C5 C 0.8678(4) 0.1879(3) 0.98492(14) 0.0300(8) Uani 1 1 d . . . H5A H 0.7737 0.1750 1.0145 0.045 Uiso 1 1 calc R . . H5B H 0.8847 0.2864 0.9767 0.045 Uiso 1 1 calc R . . H5C H 0.9612 0.1490 1.0084 0.045 Uiso 1 1 calc R . . C6 C 0.7663(3) 0.2014(3) 0.64763(16) 0.0341(8) Uani 1 1 d . . . H6A H 0.6783 0.1898 0.6808 0.051 Uiso 1 1 calc R . . H6B H 0.7321 0.1719 0.6009 0.051 Uiso 1 1 calc R . . H6C H 0.7978 0.2985 0.6461 0.051 Uiso 1 1 calc R . . C7 C 0.6940(3) 0.1683(3) 0.87698(14) 0.0238(7) Uani 1 1 d . . . C8 C 0.5837(3) 0.0771(3) 0.84930(15) 0.0297(8) Uani 1 1 d . . . H8 H 0.5996 -0.0192 0.8546 0.036 Uiso 1 1 calc R . . C9 C 0.4508(4) 0.1249(3) 0.81402(16) 0.0382(9) Uani 1 1 d . . . H9 H 0.3760 0.0613 0.7954 0.046 Uiso 1 1 calc R . . C10 C 0.4264(4) 0.2648(3) 0.80577(16) 0.0359(8) Uani 1 1 d . . . H10 H 0.3346 0.2976 0.7820 0.043 Uiso 1 1 calc R . . C11 C 0.5355(4) 0.3556(3) 0.83215(15) 0.0326(8) Uani 1 1 d . . . H11 H 0.5198 0.4518 0.8262 0.039 Uiso 1 1 calc R . . C12 C 0.6695(3) 0.3079(3) 0.86764(15) 0.0270(7) Uani 1 1 d . . . H12 H 0.7448 0.3719 0.8856 0.032 Uiso 1 1 calc R . . C13 C 1.0458(3) 0.1207(3) 0.61928(14) 0.0214(6) Uani 1 1 d . . . C14 C 1.1968(3) 0.1644(3) 0.63915(15) 0.0232(7) Uani 1 1 d . . . H14 H 1.2156 0.1921 0.6862 0.028 Uiso 1 1 calc R . . C15 C 1.3199(3) 0.1678(3) 0.59105(15) 0.0291(8) Uani 1 1 d . . . H15 H 1.4222 0.1987 0.6053 0.035 Uiso 1 1 calc R . . C16 C 1.2959(4) 0.1271(3) 0.52335(15) 0.0295(8) Uani 1 1 d . . . H16 H 1.3812 0.1286 0.4907 0.035 Uiso 1 1 calc R . . C17 C 1.1464(4) 0.0838(3) 0.50302(16) 0.0301(8) Uani 1 1 d . . . H17 H 1.1287 0.0554 0.4560 0.036 Uiso 1 1 calc R . . C18 C 1.0227(3) 0.0815(3) 0.55041(14) 0.0261(7) Uani 1 1 d . . . H18 H 0.9201 0.0525 0.5356 0.031 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 0.0262(10) 0.0436(11) 0.0331(10) 0.0054(9) -0.0054(8) 0.0056(8) F2 0.0278(10) 0.0278(10) 0.0287(9) -0.0012(8) -0.0003(8) -0.0067(8) O1 0.0439(13) 0.0211(12) 0.0289(12) 0.0024(9) 0.0048(11) -0.0007(11) O2 0.0420(13) 0.0204(12) 0.0313(12) 0.0021(9) 0.0029(11) 0.0018(11) N1 0.0267(15) 0.0210(13) 0.0222(13) 0.0013(11) 0.0020(12) -0.0011(12) C1 0.0311(18) 0.0215(17) 0.0211(15) 0.0005(13) 0.0036(14) -0.0012(14) C2 0.0242(17) 0.0232(17) 0.0249(16) 0.0036(13) -0.0044(14) 0.0015(14) C3 0.0184(16) 0.0240(17) 0.0266(16) 0.0023(14) 0.0034(14) 0.0027(14) C4 0.0232(17) 0.0267(17) 0.0241(16) -0.0003(14) -0.0008(13) -0.0031(14) C5 0.0370(19) 0.0294(17) 0.0235(17) 0.0007(14) 0.0009(15) -0.0007(15) C6 0.0187(16) 0.052(2) 0.0321(18) 0.0011(16) -0.0006(14) 0.0044(16) C7 0.0207(16) 0.0284(18) 0.0223(16) -0.0024(13) 0.0078(13) -0.0031(13) C8 0.0271(17) 0.0275(18) 0.0345(19) -0.0065(15) 0.0049(15) -0.0053(15) C9 0.0251(18) 0.048(2) 0.042(2) -0.0131(17) 0.0024(16) -0.0101(18) C10 0.0249(18) 0.051(2) 0.0316(19) -0.0070(17) -0.0034(15) 0.0067(17) C11 0.0323(19) 0.0337(19) 0.0319(18) -0.0029(15) -0.0041(16) 0.0051(17) C12 0.0250(18) 0.0288(19) 0.0273(17) -0.0049(14) 0.0012(14) -0.0039(15) C13 0.0196(15) 0.0167(15) 0.0280(17) 0.0001(13) 0.0012(13) 0.0037(14) C14 0.0247(16) 0.0239(17) 0.0209(15) -0.0021(13) -0.0007(14) -0.0002(14) C15 0.0212(17) 0.0270(18) 0.039(2) 0.0007(15) -0.0010(15) -0.0009(14) C16 0.0301(19) 0.0304(19) 0.0280(17) -0.0002(14) 0.0104(14) 0.0032(16) C17 0.0366(19) 0.0301(18) 0.0234(16) -0.0019(14) 0.0013(15) 0.0015(16) C18 0.0233(17) 0.0271(17) 0.0278(17) 0.0006(14) -0.0060(14) 0.0000(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 F1 C2 1.363(3) . ? F2 C2 1.371(3) . ? O1 C1 1.417(3) . ? O1 H1 0.8400 . ? O2 C3 1.234(3) . ? N1 C3 1.320(3) . ? N1 C4 1.453(3) . ? N1 H1A 0.8800 . ? C1 C5 1.510(4) . ? C1 C7 1.539(4) . ? C1 C2 1.543(4) . ? C2 C3 1.527(4) . ? C4 C13 1.525(4) . ? C4 C6 1.531(4) . ? C4 H4 1.0000 . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 C12 1.383(4) . ? C7 C8 1.386(4) . ? C8 C9 1.384(4) . ? C8 H8 0.9500 . ? C9 C10 1.383(4) . ? C9 H9 0.9500 . ? C10 C11 1.368(4) . ? C10 H10 0.9500 . ? C11 C12 1.393(4) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C13 C18 1.382(4) . ? C13 C14 1.390(4) . ? C14 C15 1.383(4) . ? C14 H14 0.9500 . ? C15 C16 1.366(4) . ? C15 H15 0.9500 . ? C16 C17 1.380(4) . ? C16 H16 0.9500 . ? C17 C18 1.378(4) . ? C17 H17 0.9500 . ? C18 H18 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 C1 O1 H1 109.5 . . ? C3 N1 C4 123.3(2) . . ? C3 N1 H1A 118.4 . . ? C4 N1 H1A 118.4 . . ? O1 C1 C5 105.7(2) . . ? O1 C1 C7 111.5(2) . . ? C5 C1 C7 112.3(2) . . ? O1 C1 C2 108.1(2) . . ? C5 C1 C2 111.0(2) . . ? C7 C1 C2 108.2(2) . . ? F1 C2 F2 105.5(2) . . ? F1 C2 C3 108.1(2) . . ? F2 C2 C3 109.9(2) . . ? F1 C2 C1 109.8(2) . . ? F2 C2 C1 109.9(2) . . ? C3 C2 C1 113.2(2) . . ? O2 C3 N1 125.1(3) . . ? O2 C3 C2 117.7(3) . . ? N1 C3 C2 117.1(3) . . ? N1 C4 C13 112.6(2) . . ? N1 C4 C6 108.3(2) . . ? C13 C4 C6 112.0(2) . . ? N1 C4 H4 107.9 . . ? C13 C4 H4 107.9 . . ? C6 C4 H4 107.9 . . ? C1 C5 H5A 109.5 . . ? C1 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C1 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C4 C6 H6A 109.5 . . ? C4 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C4 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C12 C7 C8 118.5(3) . . ? C12 C7 C1 120.5(3) . . ? C8 C7 C1 121.0(3) . . ? C9 C8 C7 120.7(3) . . ? C9 C8 H8 119.7 . . ? C7 C8 H8 119.7 . . ? C10 C9 C8 120.3(3) . . ? C10 C9 H9 119.9 . . ? C8 C9 H9 119.9 . . ? C11 C10 C9 119.5(3) . . ? C11 C10 H10 120.3 . . ? C9 C10 H10 120.3 . . ? C10 C11 C12 120.4(3) . . ? C10 C11 H11 119.8 . . ? C12 C11 H11 119.8 . . ? C7 C12 C11 120.6(3) . . ? C7 C12 H12 119.7 . . ? C11 C12 H12 119.7 . . ? C18 C13 C14 118.2(3) . . ? C18 C13 C4 119.9(3) . . ? C14 C13 C4 121.9(2) . . ? C15 C14 C13 120.5(3) . . ? C15 C14 H14 119.7 . . ? C13 C14 H14 119.7 . . ? C16 C15 C14 120.7(3) . . ? C16 C15 H15 119.6 . . ? C14 C15 H15 119.6 . . ? C15 C16 C17 119.2(3) . . ? C15 C16 H16 120.4 . . ? C17 C16 H16 120.4 . . ? C18 C17 C16 120.5(3) . . ? C18 C17 H17 119.8 . . ? C16 C17 H17 119.8 . . ? C17 C18 C13 120.9(3) . . ? C17 C18 H18 119.6 . . ? C13 C18 H18 119.6 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 F1 -53.0(3) . . . . ? C5 C1 C2 F1 62.5(3) . . . . ? C7 C1 C2 F1 -173.9(2) . . . . ? O1 C1 C2 F2 -168.7(2) . . . . ? C5 C1 C2 F2 -53.2(3) . . . . ? C7 C1 C2 F2 70.4(3) . . . . ? O1 C1 C2 C3 67.9(3) . . . . ? C5 C1 C2 C3 -176.6(2) . . . . ? C7 C1 C2 C3 -53.0(3) . . . . ? C4 N1 C3 O2 5.6(4) . . . . ? C4 N1 C3 C2 -170.4(2) . . . . ? F1 C2 C3 O2 57.6(3) . . . . ? F2 C2 C3 O2 172.3(2) . . . . ? C1 C2 C3 O2 -64.3(3) . . . . ? F1 C2 C3 N1 -126.1(2) . . . . ? F2 C2 C3 N1 -11.4(3) . . . . ? C1 C2 C3 N1 112.0(3) . . . . ? C3 N1 C4 C13 -110.1(3) . . . . ? C3 N1 C4 C6 125.5(3) . . . . ? O1 C1 C7 C12 168.3(2) . . . . ? C5 C1 C7 C12 49.9(4) . . . . ? C2 C1 C7 C12 -73.0(3) . . . . ? O1 C1 C7 C8 -13.3(3) . . . . ? C5 C1 C7 C8 -131.6(3) . . . . ? C2 C1 C7 C8 105.5(3) . . . . ? C12 C7 C8 C9 -1.0(4) . . . . ? C1 C7 C8 C9 -179.4(2) . . . . ? C7 C8 C9 C10 0.1(5) . . . . ? C8 C9 C10 C11 0.6(5) . . . . ? C9 C10 C11 C12 -0.6(5) . . . . ? C8 C7 C12 C11 1.0(4) . . . . ? C1 C7 C12 C11 179.5(2) . . . . ? C10 C11 C12 C7 -0.3(4) . . . . ? N1 C4 C13 C18 179.4(2) . . . . ? C6 C4 C13 C18 -58.2(4) . . . . ? N1 C4 C13 C14 0.0(4) . . . . ? C6 C4 C13 C14 122.4(3) . . . . ? C18 C13 C14 C15 -0.2(4) . . . . ? C4 C13 C14 C15 179.2(3) . . . . ? C13 C14 C15 C16 -0.6(4) . . . . ? C14 C15 C16 C17 0.7(4) . . . . ? C15 C16 C17 C18 0.0(5) . . . . ? C16 C17 C18 C13 -0.8(5) . . . . ? C14 C13 C18 C17 0.9(4) . . . . ? C4 C13 C18 C17 -178.5(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 N1 H1A O2 0.88 2.18 2.978(3) 150.4 3_756 O1 H1 O2 0.84 2.18 2.882(3) 141.1 . _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.244 _refine_diff_density_min -0.261 _refine_diff_density_rms 0.062 # Attachment '10046.cif' data_10046 _database_code_depnum_ccdc_archive 'CCDC 842565' #TrackingRef '10046.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H21 F2 N O2' _chemical_formula_sum 'C19 H21 F2 N O2' _chemical_formula_weight 333.37 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 8.8405(17) _cell_length_b 9.7476(19) _cell_length_c 19.684(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1696.3(6) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 949 _cell_measurement_theta_min 2.331 _cell_measurement_theta_max 22.316 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.305 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 704 _exptl_absorpt_coefficient_mu 0.099 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9653 _exptl_absorpt_correction_T_max 0.9873 _exptl_absorpt_process_details ; absorption correction based on 5599 reflections(SADABS);Rint 0.2678 before correction and 0.0666 after. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 2000 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 12172 _diffrn_reflns_av_R_equivalents 0.1351 _diffrn_reflns_av_sigmaI/netI 0.0843 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.07 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2987 _reflns_number_gt 2532 _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^)+(0.0464P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _chemical_absolute_configuration ,unk _refine_ls_abs_structure_Flack -0.1(9) _refine_ls_number_reflns 2987 _refine_ls_number_parameters 220 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0603 _refine_ls_R_factor_gt 0.0497 _refine_ls_wR_factor_ref 0.1055 _refine_ls_wR_factor_gt 0.0995 _refine_ls_goodness_of_fit_ref 1.007 _refine_ls_restrained_S_all 1.007 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group F1 F 0.36523(15) 0.06394(14) 0.11943(8) 0.0357(4) Uani 1 1 d . . . F2 F 0.46486(16) 0.25873(13) 0.14915(8) 0.0316(4) Uani 1 1 d . . . O1 O 0.6273(2) -0.04247(15) 0.07514(10) 0.0329(4) Uani 1 1 d . . . H1 H 0.6199 -0.0895 0.1108 0.049 Uiso 1 1 calc R . . O2 O 0.5472(2) -0.06535(15) 0.21705(10) 0.0361(4) Uani 1 1 d . . . N1 N 0.5343(2) 0.14710(19) 0.26461(11) 0.0282(5) Uani 1 1 d . . . H1A H 0.5149 0.2341 0.2564 0.034 Uiso 1 1 calc R . . C1 C 0.6256(3) 0.0985(2) 0.09199(13) 0.0260(5) Uani 1 1 d . . . C2 C 0.4957(2) 0.1213(2) 0.14402(14) 0.0264(6) Uani 1 1 d . . . C3 C 0.5267(3) 0.0605(2) 0.21345(13) 0.0264(5) Uani 1 1 d . . . C4 C 0.5729(3) 0.1084(2) 0.33412(13) 0.0265(6) Uani 1 1 d . . . H4 H 0.6086 0.0110 0.3334 0.032 Uiso 1 1 calc R . . C5 C 0.5918(3) 0.1757(2) 0.02623(14) 0.0289(6) Uani 1 1 d . . . H5A H 0.4885 0.1521 0.0107 0.035 Uiso 1 1 calc R . . H5B H 0.5944 0.2756 0.0353 0.035 Uiso 1 1 calc R . . C6 C 0.7039(3) 0.1420(3) -0.02975(15) 0.0381(7) Uani 1 1 d . . . H6A H 0.8071 0.1582 -0.0133 0.057 Uiso 1 1 calc R . . H6B H 0.6842 0.2006 -0.0692 0.057 Uiso 1 1 calc R . . H6C H 0.6929 0.0456 -0.0428 0.057 Uiso 1 1 calc R . . C7 C 0.7044(3) 0.1978(3) 0.35788(15) 0.0371(7) Uani 1 1 d . . . H7A H 0.7908 0.1852 0.3273 0.056 Uiso 1 1 calc R . . H7B H 0.7335 0.1714 0.4041 0.056 Uiso 1 1 calc R . . H7C H 0.6735 0.2944 0.3575 0.056 Uiso 1 1 calc R . . C8 C 0.7738(3) 0.1441(2) 0.12600(14) 0.0272(6) Uani 1 1 d . . . C9 C 0.8823(3) 0.0486(3) 0.14498(15) 0.0356(6) Uani 1 1 d . . . H9 H 0.8670 -0.0458 0.1350 0.043 Uiso 1 1 calc R . . C10 C 1.0124(3) 0.0894(3) 0.17820(17) 0.0488(8) Uani 1 1 d . . . H10 H 1.0855 0.0228 0.1910 0.059 Uiso 1 1 calc R . . C11 C 1.0371(3) 0.2260(3) 0.19291(16) 0.0473(8) Uani 1 1 d . . . H11 H 1.1262 0.2535 0.2162 0.057 Uiso 1 1 calc R . . C12 C 0.9319(3) 0.3214(3) 0.17358(16) 0.0418(7) Uani 1 1 d . . . H12 H 0.9487 0.4157 0.1833 0.050 Uiso 1 1 calc R . . C13 C 0.8009(3) 0.2818(3) 0.13998(14) 0.0329(6) Uani 1 1 d . . . H13 H 0.7293 0.3491 0.1265 0.040 Uiso 1 1 calc R . . C14 C 0.4357(3) 0.1161(2) 0.38124(13) 0.0262(6) Uani 1 1 d . . . C15 C 0.2919(3) 0.1481(2) 0.35731(15) 0.0312(6) Uani 1 1 d . . . H15 H 0.2770 0.1680 0.3105 0.037 Uiso 1 1 calc R . . C16 C 0.1695(3) 0.1508(3) 0.40202(17) 0.0384(7) Uani 1 1 d . . . H16 H 0.0719 0.1740 0.3853 0.046 Uiso 1 1 calc R . . C17 C 0.1871(3) 0.1210(3) 0.46914(16) 0.0406(8) Uani 1 1 d . . . H17 H 0.1027 0.1227 0.4990 0.049 Uiso 1 1 calc R . . C18 C 0.3288(3) 0.0883(3) 0.49306(15) 0.0407(7) Uani 1 1 d . . . H18 H 0.3423 0.0661 0.5397 0.049 Uiso 1 1 calc R . . C19 C 0.4519(3) 0.0877(2) 0.44962(14) 0.0345(6) Uani 1 1 d . . . H19 H 0.5495 0.0673 0.4672 0.041 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 0.0250(7) 0.0397(8) 0.0422(10) -0.0036(7) -0.0005(6) -0.0057(7) F2 0.0328(8) 0.0233(7) 0.0388(9) -0.0012(6) 0.0013(6) 0.0076(6) O1 0.0400(10) 0.0189(8) 0.0399(12) -0.0016(7) 0.0015(9) 0.0026(8) O2 0.0484(11) 0.0187(8) 0.0413(12) -0.0002(8) 0.0025(9) -0.0034(8) N1 0.0306(12) 0.0203(9) 0.0337(14) -0.0014(9) 0.0024(9) 0.0018(9) C1 0.0267(12) 0.0192(11) 0.0322(15) -0.0001(10) 0.0024(11) -0.0008(10) C2 0.0227(13) 0.0213(11) 0.0352(16) -0.0030(11) 0.0016(10) -0.0015(10) C3 0.0210(12) 0.0240(12) 0.0343(15) -0.0020(12) 0.0042(10) -0.0039(10) C4 0.0288(14) 0.0204(11) 0.0302(15) -0.0004(10) 0.0020(11) 0.0028(10) C5 0.0256(14) 0.0241(12) 0.0372(17) -0.0012(11) -0.0033(10) 0.0005(10) C6 0.0327(15) 0.0434(16) 0.0380(18) 0.0047(13) 0.0024(12) 0.0018(12) C7 0.0273(14) 0.0376(15) 0.0463(19) 0.0014(14) -0.0009(13) -0.0026(12) C8 0.0251(13) 0.0281(12) 0.0283(16) 0.0026(11) 0.0053(10) -0.0005(10) C9 0.0326(14) 0.0330(13) 0.0413(18) 0.0107(12) 0.0021(12) 0.0038(12) C10 0.0290(16) 0.0565(18) 0.061(2) 0.0227(16) -0.0033(13) 0.0068(14) C11 0.0321(16) 0.064(2) 0.046(2) 0.0153(16) -0.0086(13) -0.0143(15) C12 0.0359(15) 0.0407(15) 0.049(2) 0.0008(14) -0.0035(13) -0.0079(13) C13 0.0300(13) 0.0335(14) 0.0353(17) -0.0001(12) -0.0039(12) 0.0016(11) C14 0.0310(14) 0.0179(10) 0.0297(16) -0.0018(10) 0.0025(11) -0.0019(10) C15 0.0321(15) 0.0272(12) 0.0342(17) 0.0001(12) -0.0008(12) -0.0041(11) C16 0.0284(15) 0.0285(14) 0.058(2) 0.0001(13) 0.0047(13) -0.0017(11) C17 0.0423(17) 0.0313(14) 0.048(2) -0.0025(13) 0.0217(14) -0.0006(12) C18 0.0478(19) 0.0409(16) 0.0333(18) 0.0062(13) 0.0097(13) 0.0037(14) C19 0.0350(15) 0.0309(14) 0.0375(18) 0.0016(12) 0.0025(12) 0.0049(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 C2 1.370(3) . ? F2 C2 1.371(2) . ? O1 C1 1.414(3) . ? O1 H1 0.8400 . ? O2 C3 1.242(3) . ? N1 C3 1.316(3) . ? N1 C4 1.460(3) . ? N1 H1A 0.8800 . ? C1 C5 1.527(4) . ? C1 C8 1.537(3) . ? C1 C2 1.555(3) . ? C2 C3 1.515(4) . ? C4 C7 1.527(3) . ? C4 C14 1.528(3) . ? C4 H4 1.0000 . ? C5 C6 1.518(4) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 C9 1.388(3) . ? C8 C13 1.391(3) . ? C9 C10 1.381(4) . ? C9 H9 0.9500 . ? C10 C11 1.380(4) . ? C10 H10 0.9500 . ? C11 C12 1.370(4) . ? C11 H11 0.9500 . ? C12 C13 1.388(4) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? C14 C19 1.382(4) . ? C14 C15 1.392(4) . ? C15 C16 1.395(4) . ? C15 H15 0.9500 . ? C16 C17 1.362(4) . ? C16 H16 0.9500 . ? C17 C18 1.376(4) . ? C17 H17 0.9500 . ? C18 C19 1.384(4) . ? C18 H18 0.9500 . ? C19 H19 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 C1 O1 H1 109.5 . . ? C3 N1 C4 124.3(2) . . ? C3 N1 H1A 117.9 . . ? C4 N1 H1A 117.9 . . ? O1 C1 C5 106.39(19) . . ? O1 C1 C8 111.98(19) . . ? C5 C1 C8 113.2(2) . . ? O1 C1 C2 107.52(19) . . ? C5 C1 C2 110.1(2) . . ? C8 C1 C2 107.5(2) . . ? F1 C2 F2 104.91(17) . . ? F1 C2 C3 108.13(18) . . ? F2 C2 C3 110.6(2) . . ? F1 C2 C1 109.3(2) . . ? F2 C2 C1 109.57(19) . . ? C3 C2 C1 113.90(19) . . ? O2 C3 N1 125.6(2) . . ? O2 C3 C2 117.7(2) . . ? N1 C3 C2 116.66(19) . . ? N1 C4 C7 108.5(2) . . ? N1 C4 C14 111.8(2) . . ? C7 C4 C14 113.0(2) . . ? N1 C4 H4 107.8 . . ? C7 C4 H4 107.8 . . ? C14 C4 H4 107.8 . . ? C6 C5 C1 112.4(2) . . ? C6 C5 H5A 109.1 . . ? C1 C5 H5A 109.1 . . ? C6 C5 H5B 109.1 . . ? C1 C5 H5B 109.1 . . ? H5A C5 H5B 107.9 . . ? C5 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C5 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C4 C7 H7A 109.5 . . ? C4 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C4 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C9 C8 C13 118.4(2) . . ? C9 C8 C1 120.8(2) . . ? C13 C8 C1 120.8(2) . . ? C10 C9 C8 120.6(3) . . ? C10 C9 H9 119.7 . . ? C8 C9 H9 119.7 . . ? C11 C10 C9 120.6(3) . . ? C11 C10 H10 119.7 . . ? C9 C10 H10 119.7 . . ? C12 C11 C10 119.3(3) . . ? C12 C11 H11 120.3 . . ? C10 C11 H11 120.3 . . ? C11 C12 C13 120.6(3) . . ? C11 C12 H12 119.7 . . ? C13 C12 H12 119.7 . . ? C12 C13 C8 120.4(2) . . ? C12 C13 H13 119.8 . . ? C8 C13 H13 119.8 . . ? C19 C14 C15 118.0(2) . . ? C19 C14 C4 120.0(2) . . ? C15 C14 C4 122.0(2) . . ? C14 C15 C16 120.0(3) . . ? C14 C15 H15 120.0 . . ? C16 C15 H15 120.0 . . ? C17 C16 C15 121.3(3) . . ? C17 C16 H16 119.4 . . ? C15 C16 H16 119.4 . . ? C16 C17 C18 119.0(3) . . ? C16 C17 H17 120.5 . . ? C18 C17 H17 120.5 . . ? C17 C18 C19 120.4(3) . . ? C17 C18 H18 119.8 . . ? C19 C18 H18 119.8 . . ? C14 C19 C18 121.3(3) . . ? C14 C19 H19 119.4 . . ? C18 C19 H19 119.4 . . ? 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 O1 C1 C2 F1 -50.7(2) . . . . ? C5 C1 C2 F1 64.8(2) . . . . ? C8 C1 C2 F1 -171.43(18) . . . . ? O1 C1 C2 F2 -165.13(18) . . . . ? C5 C1 C2 F2 -49.6(2) . . . . ? C8 C1 C2 F2 74.1(2) . . . . ? O1 C1 C2 C3 70.4(2) . . . . ? C5 C1 C2 C3 -174.11(18) . . . . ? C8 C1 C2 C3 -50.4(2) . . . . ? C4 N1 C3 O2 1.9(4) . . . . ? C4 N1 C3 C2 -175.8(2) . . . . ? F1 C2 C3 O2 61.3(3) . . . . ? F2 C2 C3 O2 175.6(2) . . . . ? C1 C2 C3 O2 -60.5(3) . . . . ? F1 C2 C3 N1 -120.9(2) . . . . ? F2 C2 C3 N1 -6.5(3) . . . . ? C1 C2 C3 N1 117.4(2) . . . . ? C3 N1 C4 C7 126.1(2) . . . . ? C3 N1 C4 C14 -108.7(2) . . . . ? O1 C1 C5 C6 -56.1(3) . . . . ? C8 C1 C5 C6 67.3(3) . . . . ? C2 C1 C5 C6 -172.3(2) . . . . ? O1 C1 C8 C9 -8.3(4) . . . . ? C5 C1 C8 C9 -128.6(3) . . . . ? C2 C1 C8 C9 109.6(3) . . . . ? O1 C1 C8 C13 173.2(2) . . . . ? C5 C1 C8 C13 52.9(3) . . . . ? C2 C1 C8 C13 -68.9(3) . . . . ? C13 C8 C9 C10 1.4(4) . . . . ? C1 C8 C9 C10 -177.2(3) . . . . ? C8 C9 C10 C11 -0.3(5) . . . . ? C9 C10 C11 C12 -0.7(5) . . . . ? C10 C11 C12 C13 0.5(5) . . . . ? C11 C12 C13 C8 0.6(4) . . . . ? C9 C8 C13 C12 -1.5(4) . . . . ? C1 C8 C13 C12 177.0(3) . . . . ? N1 C4 C14 C19 -177.7(2) . . . . ? C7 C4 C14 C19 -55.0(3) . . . . ? N1 C4 C14 C15 3.9(3) . . . . ? C7 C4 C14 C15 126.5(2) . . . . ? C19 C14 C15 C16 0.1(3) . . . . ? C4 C14 C15 C16 178.5(2) . . . . ? C14 C15 C16 C17 -0.8(4) . . . . ? C15 C16 C17 C18 0.4(4) . . . . ? C16 C17 C18 C19 0.8(4) . . . . ? C15 C14 C19 C18 1.2(4) . . . . ? C4 C14 C19 C18 -177.3(2) . . . . ? C17 C18 C19 C14 -1.7(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 H1A O2 0.88 2.10 2.916(2) 154.6 3_655 O1 H1 O2 0.84 2.20 2.890(3) 139.3 . _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.214 _refine_diff_density_min -0.269 _refine_diff_density_rms 0.060 # Attachment '10051.cif' data_10051 _database_code_depnum_ccdc_archive 'CCDC 842566' #TrackingRef '10051.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H21 F2 N O2' _chemical_formula_sum 'C20 H21 F2 N O2' _chemical_formula_weight 345.38 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 8.5802(18) _cell_length_b 9.972(2) _cell_length_c 19.406(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1660.4(6) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 1014 _cell_measurement_theta_min 2.596 _cell_measurement_theta_max 25.299 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.382 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 728 _exptl_absorpt_coefficient_mu 0.104 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9715 _exptl_absorpt_correction_T_max 0.9816 _exptl_absorpt_process_details ; absorption correction based on 6405 reflections(SADABS);Rint 0.1520 before correction and 0.0543 after. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 2000 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 11962 _diffrn_reflns_av_R_equivalents 0.0704 _diffrn_reflns_av_sigmaI/netI 0.0516 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.10 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2917 _reflns_number_gt 2639 _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^)+(0.0505P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _chemical_absolute_configuration ,unk _refine_ls_abs_structure_Flack 0.0(8) _refine_ls_number_reflns 2917 _refine_ls_number_parameters 227 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0477 _refine_ls_R_factor_gt 0.0421 _refine_ls_wR_factor_ref 0.0981 _refine_ls_wR_factor_gt 0.0954 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.034 _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 -0.08006(14) 0.38807(13) 0.10865(6) 0.0293(3) Uani 1 1 d . . . F2 F -0.02879(14) 0.58588(12) 0.14943(6) 0.0275(3) Uani 1 1 d . . . O1 O 0.14790(18) 0.54732(17) 0.03932(7) 0.0293(4) Uani 1 1 d . . . H1 H 0.0529 0.5409 0.0293 0.044 Uiso 1 1 calc R . . O2 O 0.0656(2) 0.27463(15) 0.21925(8) 0.0327(4) Uani 1 1 d . . . N1 N 0.0603(2) 0.48267(18) 0.26619(8) 0.0255(4) Uani 1 1 d . . . H1A H 0.0362 0.5672 0.2587 0.031 Uiso 1 1 calc R . . C1 C 0.1812(2) 0.4646(2) 0.09716(10) 0.0217(5) Uani 1 1 d . . . C2 C 0.0322(2) 0.4592(2) 0.14259(11) 0.0230(5) Uani 1 1 d . . . C3 C 0.0520(2) 0.3967(2) 0.21412(11) 0.0233(5) Uani 1 1 d . . . C4 C 0.1079(2) 0.4425(2) 0.33559(11) 0.0258(5) Uani 1 1 d . . . H4 H 0.1584 0.3523 0.3323 0.031 Uiso 1 1 calc R . . C5 C 0.2120(3) 0.3238(2) 0.06904(12) 0.0278(5) Uani 1 1 d . . . H5A H 0.1890 0.2570 0.1054 0.033 Uiso 1 1 calc R . . H5B H 0.1411 0.3064 0.0298 0.033 Uiso 1 1 calc R . . C6 C 0.3786(3) 0.3067(2) 0.04548(12) 0.0302(6) Uani 1 1 d . . . H6A H 0.3922 0.2172 0.0242 0.036 Uiso 1 1 calc R . . H6B H 0.4044 0.3756 0.0106 0.036 Uiso 1 1 calc R . . C7 C 0.4848(3) 0.3205(2) 0.10648(13) 0.0350(6) Uani 1 1 d . . . H7A H 0.5945 0.3142 0.0910 0.042 Uiso 1 1 calc R . . H7B H 0.4651 0.2460 0.1391 0.042 Uiso 1 1 calc R . . C8 C 0.4598(2) 0.4526(2) 0.14277(11) 0.0266(5) Uani 1 1 d . . . C9 C 0.3187(2) 0.5221(2) 0.13739(11) 0.0229(5) Uani 1 1 d . . . C10 C 0.3077(3) 0.6502(2) 0.16604(12) 0.0286(5) Uani 1 1 d . . . H10 H 0.2131 0.6990 0.1615 0.034 Uiso 1 1 calc R . . C11 C 0.4316(3) 0.7075(2) 0.20081(13) 0.0356(6) Uani 1 1 d . . . H11 H 0.4220 0.7951 0.2196 0.043 Uiso 1 1 calc R . . C12 C 0.5688(3) 0.6375(3) 0.20821(13) 0.0355(6) Uani 1 1 d . . . H12 H 0.6536 0.6755 0.2330 0.043 Uiso 1 1 calc R . . C13 C 0.5821(3) 0.5112(3) 0.17917(12) 0.0327(6) Uani 1 1 d . . . H13 H 0.6771 0.4632 0.1842 0.039 Uiso 1 1 calc R . . C14 C 0.2303(3) 0.5423(3) 0.36080(13) 0.0395(6) Uani 1 1 d . . . H14A H 0.3195 0.5418 0.3292 0.059 Uiso 1 1 calc R . . H14B H 0.2651 0.5167 0.4071 0.059 Uiso 1 1 calc R . . H14C H 0.1849 0.6324 0.3623 0.059 Uiso 1 1 calc R . . C15 C -0.0274(3) 0.4313(2) 0.38491(11) 0.0240(5) Uani 1 1 d . . . C16 C -0.1763(3) 0.4757(2) 0.36959(13) 0.0324(6) Uani 1 1 d . . . H16 H -0.1976 0.5140 0.3258 0.039 Uiso 1 1 calc R . . C17 C -0.2943(3) 0.4643(3) 0.41800(15) 0.0406(6) Uani 1 1 d . . . H17 H -0.3965 0.4938 0.4069 0.049 Uiso 1 1 calc R . . C18 C -0.2651(3) 0.4111(3) 0.48148(15) 0.0459(7) Uani 1 1 d . . . H18 H -0.3464 0.4050 0.5146 0.055 Uiso 1 1 calc R . . C19 C -0.1179(4) 0.3664(3) 0.49754(13) 0.0412(7) Uani 1 1 d . . . H19 H -0.0974 0.3292 0.5417 0.049 Uiso 1 1 calc R . . C20 C -0.0006(3) 0.3757(2) 0.44956(12) 0.0313(5) Uani 1 1 d . . . H20 H 0.1005 0.3436 0.4607 0.038 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 0.0236(7) 0.0338(7) 0.0307(7) -0.0034(6) -0.0041(6) -0.0041(6) F2 0.0274(6) 0.0229(7) 0.0320(7) 0.0000(6) 0.0006(6) 0.0073(5) O1 0.0246(8) 0.0372(10) 0.0260(8) 0.0078(8) -0.0016(7) 0.0023(7) O2 0.0485(11) 0.0186(9) 0.0311(9) 0.0006(7) 0.0003(8) 0.0012(7) N1 0.0362(11) 0.0172(9) 0.0231(10) 0.0010(8) -0.0003(8) 0.0030(8) C1 0.0239(11) 0.0188(11) 0.0224(11) 0.0014(9) 0.0005(9) 0.0005(9) C2 0.0212(10) 0.0206(11) 0.0273(12) -0.0015(10) -0.0043(9) 0.0017(9) C3 0.0193(11) 0.0234(12) 0.0273(12) 0.0007(10) 0.0014(9) -0.0023(9) C4 0.0289(12) 0.0244(12) 0.0241(11) -0.0003(9) 0.0002(10) 0.0015(10) C5 0.0312(13) 0.0239(12) 0.0283(12) -0.0039(10) 0.0005(10) 0.0007(10) C6 0.0361(13) 0.0225(13) 0.0318(13) -0.0016(10) 0.0076(11) 0.0014(10) C7 0.0319(13) 0.0308(13) 0.0422(15) 0.0011(11) 0.0022(12) 0.0080(11) C8 0.0241(11) 0.0292(12) 0.0265(12) 0.0052(11) 0.0029(10) 0.0019(10) C9 0.0236(11) 0.0226(11) 0.0224(11) 0.0033(10) 0.0015(9) -0.0031(9) C10 0.0282(12) 0.0214(12) 0.0361(13) -0.0009(10) -0.0001(11) 0.0002(10) C11 0.0401(15) 0.0267(14) 0.0398(14) -0.0027(11) -0.0017(12) -0.0087(11) C12 0.0325(14) 0.0418(15) 0.0322(13) 0.0031(12) -0.0050(11) -0.0126(11) C13 0.0253(12) 0.0403(15) 0.0325(13) 0.0079(11) -0.0017(11) -0.0015(11) C14 0.0358(14) 0.0505(16) 0.0323(13) 0.0010(13) -0.0020(12) -0.0144(12) C15 0.0305(12) 0.0152(10) 0.0262(12) -0.0046(9) -0.0006(10) -0.0036(9) C16 0.0353(13) 0.0194(12) 0.0426(14) -0.0004(11) 0.0014(11) 0.0013(10) C17 0.0323(14) 0.0232(13) 0.0662(18) -0.0054(14) 0.0104(13) 0.0014(11) C18 0.0537(18) 0.0285(14) 0.0555(18) -0.0129(13) 0.0291(15) -0.0098(14) C19 0.065(2) 0.0285(14) 0.0296(14) -0.0042(11) 0.0092(13) -0.0135(14) C20 0.0398(14) 0.0269(12) 0.0273(12) -0.0036(10) -0.0014(11) -0.0083(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 C2 1.366(2) . ? F2 C2 1.373(2) . ? O1 C1 1.422(2) . ? O1 H1 0.8400 . ? O2 C3 1.227(3) . ? N1 C3 1.327(3) . ? N1 C4 1.463(3) . ? N1 H1A 0.8800 . ? C1 C9 1.526(3) . ? C1 C5 1.530(3) . ? C1 C2 1.554(3) . ? C2 C3 1.531(3) . ? C4 C15 1.509(3) . ? C4 C14 1.527(3) . ? C4 H4 1.0000 . ? C5 C6 1.510(3) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.500(3) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.509(3) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C13 1.394(3) . ? C8 C9 1.398(3) . ? C9 C10 1.396(3) . ? C10 C11 1.383(3) . ? C10 H10 0.9500 . ? C11 C12 1.377(4) . ? C11 H11 0.9500 . ? C12 C13 1.385(4) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 C16 1.384(3) . ? C15 C20 1.391(3) . ? C16 C17 1.386(3) . ? C16 H16 0.9500 . ? C17 C18 1.364(4) . ? C17 H17 0.9500 . ? C18 C19 1.375(4) . ? C18 H18 0.9500 . ? C19 C20 1.374(3) . ? C19 H19 0.9500 . ? C20 H20 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 C1 O1 H1 109.5 . . ? C3 N1 C4 122.61(18) . . ? C3 N1 H1A 118.7 . . ? C4 N1 H1A 118.7 . . ? O1 C1 C9 109.98(16) . . ? O1 C1 C5 106.59(17) . . ? C9 C1 C5 113.17(17) . . ? O1 C1 C2 107.61(16) . . ? C9 C1 C2 111.03(16) . . ? C5 C1 C2 108.22(18) . . ? F1 C2 F2 104.81(15) . . ? F1 C2 C3 107.70(17) . . ? F2 C2 C3 109.21(17) . . ? F1 C2 C1 108.95(16) . . ? F2 C2 C1 109.66(17) . . ? C3 C2 C1 115.92(16) . . ? O2 C3 N1 125.0(2) . . ? O2 C3 C2 119.2(2) . . ? N1 C3 C2 115.68(18) . . ? N1 C4 C15 112.90(17) . . ? N1 C4 C14 107.96(19) . . ? C15 C4 C14 111.97(18) . . ? N1 C4 H4 107.9 . . ? C15 C4 H4 107.9 . . ? C14 C4 H4 107.9 . . ? C6 C5 C1 112.06(19) . . ? C6 C5 H5A 109.2 . . ? C1 C5 H5A 109.2 . . ? C6 C5 H5B 109.2 . . ? C1 C5 H5B 109.2 . . ? H5A C5 H5B 107.9 . . ? C7 C6 C5 109.00(19) . . ? C7 C6 H6A 109.9 . . ? C5 C6 H6A 109.9 . . ? C7 C6 H6B 109.9 . . ? C5 C6 H6B 109.9 . . ? H6A C6 H6B 108.3 . . ? C6 C7 C8 111.2(2) . . ? C6 C7 H7A 109.4 . . ? C8 C7 H7A 109.4 . . ? C6 C7 H7B 109.4 . . ? C8 C7 H7B 109.4 . . ? H7A C7 H7B 108.0 . . ? C13 C8 C9 118.8(2) . . ? C13 C8 C7 119.7(2) . . ? C9 C8 C7 121.4(2) . . ? C10 C9 C8 118.8(2) . . ? C10 C9 C1 119.65(19) . . ? C8 C9 C1 121.41(18) . . ? C11 C10 C9 121.4(2) . . ? C11 C10 H10 119.3 . . ? C9 C10 H10 119.3 . . ? C12 C11 C10 119.9(2) . . ? C12 C11 H11 120.0 . . ? C10 C11 H11 120.0 . . ? C11 C12 C13 119.3(2) . . ? C11 C12 H12 120.4 . . ? C13 C12 H12 120.4 . . ? C12 C13 C8 121.7(2) . . ? C12 C13 H13 119.2 . . ? C8 C13 H13 119.2 . . ? C4 C14 H14A 109.5 . . ? C4 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C4 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C16 C15 C20 118.3(2) . . ? C16 C15 C4 123.4(2) . . ? C20 C15 C4 118.31(19) . . ? C15 C16 C17 120.2(2) . . ? C15 C16 H16 119.9 . . ? C17 C16 H16 119.9 . . ? C18 C17 C16 120.6(3) . . ? C18 C17 H17 119.7 . . ? C16 C17 H17 119.7 . . ? C17 C18 C19 120.0(3) . . ? C17 C18 H18 120.0 . . ? C19 C18 H18 120.0 . . ? C20 C19 C18 119.8(3) . . ? C20 C19 H19 120.1 . . ? C18 C19 H19 120.1 . . ? C19 C20 C15 121.1(2) . . ? C19 C20 H20 119.4 . . ? C15 C20 H20 119.4 . . ? 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 O1 C1 C2 F1 69.2(2) . . . . ? C9 C1 C2 F1 -170.36(16) . . . . ? C5 C1 C2 F1 -45.6(2) . . . . ? O1 C1 C2 F2 -44.9(2) . . . . ? C9 C1 C2 F2 75.5(2) . . . . ? C5 C1 C2 F2 -159.77(17) . . . . ? O1 C1 C2 C3 -169.14(17) . . . . ? C9 C1 C2 C3 -48.7(2) . . . . ? C5 C1 C2 C3 76.0(2) . . . . ? C4 N1 C3 O2 8.5(3) . . . . ? C4 N1 C3 C2 -168.29(18) . . . . ? F1 C2 C3 O2 47.9(3) . . . . ? F2 C2 C3 O2 161.14(18) . . . . ? C1 C2 C3 O2 -74.4(3) . . . . ? F1 C2 C3 N1 -135.15(19) . . . . ? F2 C2 C3 N1 -21.9(2) . . . . ? C1 C2 C3 N1 102.6(2) . . . . ? C3 N1 C4 C15 -103.8(2) . . . . ? C3 N1 C4 C14 131.9(2) . . . . ? O1 C1 C5 C6 84.2(2) . . . . ? C9 C1 C5 C6 -36.8(3) . . . . ? C2 C1 C5 C6 -160.34(18) . . . . ? C1 C5 C6 C7 64.1(3) . . . . ? C5 C6 C7 C8 -56.0(3) . . . . ? C6 C7 C8 C13 -152.3(2) . . . . ? C6 C7 C8 C9 23.9(3) . . . . ? C13 C8 C9 C10 2.8(3) . . . . ? C7 C8 C9 C10 -173.4(2) . . . . ? C13 C8 C9 C1 178.88(19) . . . . ? C7 C8 C9 C1 2.7(3) . . . . ? O1 C1 C9 C10 60.8(2) . . . . ? C5 C1 C9 C10 179.9(2) . . . . ? C2 C1 C9 C10 -58.2(3) . . . . ? O1 C1 C9 C8 -115.3(2) . . . . ? C5 C1 C9 C8 3.8(3) . . . . ? C2 C1 C9 C8 125.8(2) . . . . ? C8 C9 C10 C11 -1.6(3) . . . . ? C1 C9 C10 C11 -177.8(2) . . . . ? C9 C10 C11 C12 -0.5(4) . . . . ? C10 C11 C12 C13 1.5(4) . . . . ? C11 C12 C13 C8 -0.2(4) . . . . ? C9 C8 C13 C12 -1.9(3) . . . . ? C7 C8 C13 C12 174.3(2) . . . . ? N1 C4 C15 C16 -10.1(3) . . . . ? C14 C4 C15 C16 112.0(2) . . . . ? N1 C4 C15 C20 170.99(18) . . . . ? C14 C4 C15 C20 -66.9(3) . . . . ? C20 C15 C16 C17 0.0(3) . . . . ? C4 C15 C16 C17 -178.8(2) . . . . ? C15 C16 C17 C18 0.9(4) . . . . ? C16 C17 C18 C19 -1.0(4) . . . . ? C17 C18 C19 C20 0.1(4) . . . . ? C18 C19 C20 C15 0.8(4) . . . . ? C16 C15 C20 C19 -0.9(3) . . . . ? C4 C15 C20 C19 178.1(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 O1 H1 F1 0.84 2.45 2.856(2) 110.7 . N1 H1A O2 0.88 2.29 3.118(2) 157.8 3 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.348 _refine_diff_density_min -0.269 _refine_diff_density_rms 0.043