# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_her _database_code_depnum_ccdc_archive 'CCDC 887849' #TrackingRef '29a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H25 F3 N2 O5' _chemical_formula_weight 430.42 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0727 0.0534 '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 6.34460(10) _cell_length_b 16.7461(2) _cell_length_c 19.6159(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2084.14(5) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 7557 _cell_measurement_theta_min 3.4673 _cell_measurement_theta_max 74.7116 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.298 _exptl_crystal_size_mid 0.106 _exptl_crystal_size_min 0.091 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.372 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 904 _exptl_absorpt_coefficient_mu 0.993 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.37445 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details 'CrysAlisPro, Agilent Technologies' _exptl_special_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'SuperNova (Cu) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 10.3468 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11926 _diffrn_reflns_av_R_equivalents 0.0250 _diffrn_reflns_av_sigmaI/netI 0.0242 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 3.47 _diffrn_reflns_theta_max 74.89 _reflns_number_total 4175 _reflns_number_gt 4068 _reflns_threshold_expression >2\s(I) _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) ; _computing_structure_solution 'SHELXS-97 (SHELDRICK, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _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^ > 2\s(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^)+(0.0462P)^2^+0.1985P] 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 -0.02(9) _refine_ls_number_reflns 4175 _refine_ls_number_parameters 275 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0303 _refine_ls_R_factor_gt 0.0295 _refine_ls_wR_factor_ref 0.0758 _refine_ls_wR_factor_gt 0.0751 _refine_ls_goodness_of_fit_ref 1.059 _refine_ls_restrained_S_all 1.059 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _chemical_absolute_configuration ad loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.1021(2) 0.87613(7) 0.93825(6) 0.0181(2) Uani 1 1 d . . . C2 C -0.2322(2) 0.83376(8) 0.96535(7) 0.0226(3) Uani 1 1 d . . . H2A H -0.3153 0.8720 0.9929 0.027 Uiso 1 1 calc R . . H2B H -0.2909 0.7795 0.9719 0.027 Uiso 1 1 calc R . . C3 C -0.23613(19) 0.85717(7) 0.88990(7) 0.0202(2) Uani 1 1 d . . . H3 H -0.3487 0.8980 0.8823 0.024 Uiso 1 1 calc R . . C4 C 0.0238(2) 0.93951(7) 0.82510(6) 0.0185(2) Uani 1 1 d . . . C5 C -0.2712(2) 0.78672(8) 0.84131(7) 0.0233(3) Uani 1 1 d . . . H5A H -0.4119 0.7637 0.8508 0.028 Uiso 1 1 calc R . . H5B H -0.2738 0.8075 0.7941 0.028 Uiso 1 1 calc R . . C6 C -0.1104(2) 0.72055(7) 0.84499(6) 0.0198(2) Uani 1 1 d . . . C7 C -0.1560(2) 0.64813(8) 0.87708(7) 0.0220(3) Uani 1 1 d . . . H7 H -0.2884 0.6410 0.8989 0.026 Uiso 1 1 calc R . . C8 C -0.0100(3) 0.58636(8) 0.87755(7) 0.0270(3) Uani 1 1 d . . . H8 H -0.0436 0.5374 0.8995 0.032 Uiso 1 1 calc R . . C9 C 0.1844(2) 0.59561(9) 0.84626(7) 0.0281(3) Uani 1 1 d . . . H9 H 0.2837 0.5532 0.8464 0.034 Uiso 1 1 calc R . . C10 C 0.2324(2) 0.66773(9) 0.81474(7) 0.0287(3) Uani 1 1 d . . . H10 H 0.3658 0.6748 0.7936 0.034 Uiso 1 1 calc R . . C11 C 0.0870(2) 0.72926(8) 0.81403(7) 0.0245(3) Uani 1 1 d . . . H11 H 0.1217 0.7782 0.7922 0.029 Uiso 1 1 calc R . . C13 C 0.2235(2) 1.05919(7) 0.86544(6) 0.0202(3) Uani 1 1 d . . . H13 H 0.1586 1.0441 0.9101 0.024 Uiso 1 1 calc R . . C14 C 0.4374(2) 1.09391(8) 0.88152(7) 0.0248(3) Uani 1 1 d . . . C15 C 0.0804(2) 1.12268(8) 0.83402(8) 0.0286(3) Uani 1 1 d . . . H15A H 0.0615 1.1666 0.8664 0.043 Uiso 1 1 calc R . . H15B H -0.0569 1.0990 0.8233 0.043 Uiso 1 1 calc R . . H15C H 0.1450 1.1431 0.7921 0.043 Uiso 1 1 calc R . . C12 C 0.2388(2) 0.98154(7) 0.82313(6) 0.0179(2) Uani 1 1 d . . . H12 H 0.3452 0.9458 0.8451 0.021 Uiso 1 1 calc R . . C16 C 0.3697(2) 0.93069(8) 0.71725(6) 0.0189(2) Uani 1 1 d . . . C17 C 0.4827(2) 0.89049(8) 0.60346(6) 0.0237(3) Uani 1 1 d . . . C18 C 0.6879(2) 0.85240(9) 0.62702(7) 0.0298(3) Uani 1 1 d . . . H18A H 0.7855 0.8942 0.6421 0.045 Uiso 1 1 calc R . . H18B H 0.7512 0.8227 0.5892 0.045 Uiso 1 1 calc R . . H18C H 0.6593 0.8159 0.6649 0.045 Uiso 1 1 calc R . . C19 C 0.3083(3) 0.83003(10) 0.59185(8) 0.0327(3) Uani 1 1 d . . . H19A H 0.2847 0.7995 0.6338 0.049 Uiso 1 1 calc R . . H19B H 0.3491 0.7936 0.5551 0.049 Uiso 1 1 calc R . . H19C H 0.1783 0.8580 0.5792 0.049 Uiso 1 1 calc R . . C20 C 0.5210(3) 0.94076(10) 0.53976(7) 0.0343(3) Uani 1 1 d . . . H20A H 0.3912 0.9691 0.5276 0.051 Uiso 1 1 calc R . . H20B H 0.5631 0.9059 0.5020 0.051 Uiso 1 1 calc R . . H20C H 0.6332 0.9796 0.5488 0.051 Uiso 1 1 calc R . . F1 F 0.52988(15) 1.12906(6) 0.82823(5) 0.0366(2) Uani 1 1 d . . . F2 F 0.42160(16) 1.15051(5) 0.93000(5) 0.0355(2) Uani 1 1 d . . . F3 F 0.57467(16) 1.03998(5) 0.90553(6) 0.0421(2) Uani 1 1 d . . . N1 N -0.02804(16) 0.89542(6) 0.88339(5) 0.0173(2) Uani 1 1 d . . . N2 N 0.30402(19) 0.99594(6) 0.75347(5) 0.0208(2) Uani 1 1 d . . . H2 H 0.3015 1.0440 0.7354 0.025 Uiso 1 1 calc R . . O1 O -0.10274(16) 0.94516(6) 0.77929(5) 0.0268(2) Uani 1 1 d . . . O2 O 0.41111(16) 0.95183(5) 0.65246(5) 0.02189(19) Uani 1 1 d . . . O3 O 0.28595(15) 0.89163(6) 0.94609(5) 0.0254(2) Uani 1 1 d . . . O4 O 0.38897(16) 0.86457(5) 0.74160(5) 0.02276(19) Uani 1 1 d . . . O5 O -0.01135(15) 0.83607(5) 0.98471(4) 0.02207(19) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0185(6) 0.0170(5) 0.0189(5) 0.0025(4) 0.0004(5) 0.0006(5) C2 0.0166(6) 0.0244(6) 0.0269(6) 0.0006(5) 0.0030(5) -0.0036(5) C3 0.0135(6) 0.0187(5) 0.0284(6) 0.0015(5) -0.0005(5) -0.0011(4) C4 0.0190(6) 0.0162(5) 0.0203(5) 0.0023(4) -0.0012(5) 0.0019(5) C5 0.0207(6) 0.0204(6) 0.0287(6) 0.0007(5) -0.0062(5) -0.0039(5) C6 0.0202(6) 0.0200(5) 0.0193(5) -0.0029(4) -0.0029(5) -0.0032(5) C7 0.0219(6) 0.0220(6) 0.0222(6) -0.0022(5) 0.0009(5) -0.0048(5) C8 0.0327(7) 0.0207(6) 0.0276(6) -0.0017(5) -0.0033(6) -0.0001(6) C9 0.0247(7) 0.0262(6) 0.0335(7) -0.0111(5) -0.0043(6) 0.0041(6) C10 0.0214(7) 0.0320(7) 0.0326(7) -0.0142(6) 0.0030(5) -0.0048(6) C11 0.0255(7) 0.0231(6) 0.0250(6) -0.0056(5) 0.0049(5) -0.0078(5) C13 0.0213(6) 0.0189(6) 0.0205(6) 0.0011(4) 0.0022(5) -0.0013(5) C14 0.0264(7) 0.0205(6) 0.0276(6) 0.0002(5) -0.0017(5) -0.0022(5) C15 0.0262(7) 0.0219(6) 0.0379(7) 0.0000(5) -0.0007(6) 0.0039(6) C12 0.0183(6) 0.0184(5) 0.0170(5) 0.0027(4) 0.0011(4) 0.0003(5) C16 0.0168(6) 0.0205(5) 0.0195(5) 0.0014(4) 0.0003(5) -0.0015(5) C17 0.0249(6) 0.0262(6) 0.0199(5) -0.0034(5) 0.0002(5) 0.0043(5) C18 0.0250(7) 0.0368(7) 0.0275(6) -0.0035(6) 0.0001(5) 0.0069(6) C19 0.0302(7) 0.0338(7) 0.0343(7) -0.0084(6) -0.0046(6) -0.0007(7) C20 0.0438(9) 0.0397(8) 0.0193(6) 0.0015(5) 0.0048(6) 0.0063(7) F1 0.0295(5) 0.0436(5) 0.0367(4) 0.0014(4) 0.0070(4) -0.0143(4) F2 0.0443(5) 0.0275(4) 0.0346(4) -0.0091(3) -0.0004(4) -0.0090(4) F3 0.0359(5) 0.0280(4) 0.0625(6) -0.0020(4) -0.0249(5) 0.0002(4) N1 0.0139(5) 0.0173(4) 0.0207(5) 0.0020(4) -0.0008(4) -0.0003(4) N2 0.0257(6) 0.0186(5) 0.0181(5) 0.0032(4) 0.0023(4) 0.0012(4) O1 0.0247(5) 0.0292(5) 0.0265(5) 0.0067(4) -0.0082(4) -0.0031(4) O2 0.0269(5) 0.0206(4) 0.0182(4) 0.0019(3) 0.0022(4) 0.0018(4) O3 0.0167(5) 0.0352(5) 0.0242(4) 0.0081(4) -0.0030(3) -0.0027(4) O4 0.0251(5) 0.0198(4) 0.0234(4) 0.0038(3) 0.0022(4) 0.0017(4) O5 0.0189(4) 0.0250(4) 0.0223(4) 0.0065(3) 0.0013(3) -0.0014(4) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O3 1.2046(17) . ? C1 O5 1.3412(15) . ? C1 N1 1.3944(16) . ? C2 O5 1.4522(16) . ? C2 C3 1.5312(18) . ? C3 N1 1.4730(16) . ? C3 C5 1.5331(17) . ? C4 O1 1.2087(17) . ? C4 N1 1.4002(15) . ? C4 C12 1.5356(18) . ? C5 C6 1.5080(18) . ? C6 C7 1.3966(17) . ? C6 C11 1.4000(19) . ? C7 C8 1.388(2) . ? C8 C9 1.386(2) . ? C9 C10 1.391(2) . ? C10 C11 1.383(2) . ? C13 C14 1.5096(19) . ? C13 C15 1.5279(19) . ? C13 C12 1.5456(16) . ? C14 F1 1.3355(17) . ? C14 F3 1.3403(17) . ? C14 F2 1.3463(16) . ? C12 N2 1.4479(15) . ? C16 O4 1.2120(16) . ? C16 O2 1.3451(15) . ? C16 N2 1.3684(17) . ? C17 O2 1.4784(15) . ? C17 C19 1.517(2) . ? C17 C18 1.522(2) . ? C17 C20 1.5260(19) . ? 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 O3 C1 O5 122.73(12) . . ? O3 C1 N1 128.46(12) . . ? O5 C1 N1 108.80(11) . . ? O5 C2 C3 105.17(10) . . ? N1 C3 C2 100.40(10) . . ? N1 C3 C5 114.27(11) . . ? C2 C3 C5 113.97(10) . . ? O1 C4 N1 119.50(12) . . ? O1 C4 C12 122.38(11) . . ? N1 C4 C12 118.09(11) . . ? C6 C5 C3 115.94(11) . . ? C7 C6 C11 118.11(12) . . ? C7 C6 C5 121.32(12) . . ? C11 C6 C5 120.54(12) . . ? C8 C7 C6 120.79(13) . . ? C9 C8 C7 120.48(13) . . ? C8 C9 C10 119.27(13) . . ? C11 C10 C9 120.35(13) . . ? C10 C11 C6 120.99(13) . . ? C14 C13 C15 110.50(11) . . ? C14 C13 C12 112.32(11) . . ? C15 C13 C12 113.96(11) . . ? F1 C14 F3 106.64(12) . . ? F1 C14 F2 105.97(11) . . ? F3 C14 F2 105.94(11) . . ? F1 C14 C13 113.65(11) . . ? F3 C14 C13 113.46(11) . . ? F2 C14 C13 110.61(12) . . ? N2 C12 C4 110.72(10) . . ? N2 C12 C13 112.62(10) . . ? C4 C12 C13 108.43(10) . . ? O4 C16 O2 126.37(12) . . ? O4 C16 N2 123.75(11) . . ? O2 C16 N2 109.87(10) . . ? O2 C17 C19 109.69(12) . . ? O2 C17 C18 110.90(11) . . ? C19 C17 C18 112.96(12) . . ? O2 C17 C20 101.42(10) . . ? C19 C17 C20 111.18(12) . . ? C18 C17 C20 110.10(13) . . ? C1 N1 C4 127.82(11) . . ? C1 N1 C3 111.30(10) . . ? C4 N1 C3 120.70(10) . . ? C16 N2 C12 116.37(10) . . ? C16 O2 C17 119.44(10) . . ? C1 O5 C2 110.70(10) . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 74.89 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.272 _refine_diff_density_min -0.279 _refine_diff_density_rms 0.047 data_he0112a _database_code_depnum_ccdc_archive 'CCDC 887850' #TrackingRef '30a.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H27 F3 N2 O5' _chemical_formula_weight 444.45 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting 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 6.3032(14) _cell_length_b 17.505(4) _cell_length_c 19.677(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2171.1(8) _cell_formula_units_Z 4 _cell_measurement_temperature 133(2) _cell_measurement_reflns_used 989 _cell_measurement_theta_min 3.4 _cell_measurement_theta_max 30.5 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.8 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.360 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 936 _exptl_absorpt_coefficient_mu 0.113 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.705 _exptl_absorpt_correction_T_max 0.746 _exptl_absorpt_process_details 'BRUKER-AXS SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 133(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'BRUKER-AXS SMART CCD' _diffrn_measurement_method 'omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 35355 _diffrn_reflns_av_R_equivalents 0.0254 _diffrn_reflns_av_sigmaI/netI 0.0183 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.07 _diffrn_reflns_theta_max 30.60 _reflns_number_total 6616 _reflns_number_gt 6156 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (BRUKER-AXS)' _computing_cell_refinement 'SAINT (BRUKER-AXS)' _computing_data_reduction 'SAINT (BRUKER-AXS)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0524P)^2^+0.2787P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.1(4) _refine_ls_number_reflns 6616 _refine_ls_number_parameters 288 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0384 _refine_ls_R_factor_gt 0.0346 _refine_ls_wR_factor_ref 0.0886 _refine_ls_wR_factor_gt 0.0859 _refine_ls_goodness_of_fit_ref 1.063 _refine_ls_restrained_S_all 1.063 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _chemical_absolute_configuration syn loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.11536(17) 0.87770(6) 0.43888(5) 0.01766(19) Uani 1 1 d . . . C2 C -0.21683(19) 0.83249(7) 0.46611(6) 0.0231(2) Uani 1 1 d . . . H2A H -0.2997 0.8660 0.4968 0.028 Uiso 1 1 calc R . . H2B H -0.2727 0.7798 0.4696 0.028 Uiso 1 1 calc R . . C3 C -0.22928(16) 0.86127(6) 0.39269(6) 0.01894(19) Uani 1 1 d . . . H3 H -0.3439 0.9006 0.3892 0.023 Uiso 1 1 calc R . . C4 C 0.02354(17) 0.94625(6) 0.33076(5) 0.01707(18) Uani 1 1 d . . . C5 C -0.26945(18) 0.79829(6) 0.34022(6) 0.0215(2) Uani 1 1 d . . . H5A H -0.4104 0.7755 0.3494 0.026 Uiso 1 1 calc R . . H5B H -0.2754 0.8220 0.2946 0.026 Uiso 1 1 calc R . . C6 C -0.10781(17) 0.73503(6) 0.33861(5) 0.01809(19) Uani 1 1 d . . . C7 C 0.08602(19) 0.74526(7) 0.30522(6) 0.0227(2) Uani 1 1 d . . . H7 H 0.1168 0.7930 0.2844 0.027 Uiso 1 1 calc R . . C8 C 0.2334(2) 0.68683(7) 0.30213(6) 0.0273(2) Uani 1 1 d . . . H8 H 0.3645 0.6949 0.2794 0.033 Uiso 1 1 calc R . . C9 C 0.1916(2) 0.61653(7) 0.33201(7) 0.0288(2) Uani 1 1 d . . . H9 H 0.2927 0.5764 0.3296 0.035 Uiso 1 1 calc R . . C10 C 0.0001(2) 0.60571(7) 0.36550(6) 0.0273(2) Uani 1 1 d . . . H10 H -0.0297 0.5579 0.3863 0.033 Uiso 1 1 calc R . . C11 C -0.14821(19) 0.66431(6) 0.36879(6) 0.0222(2) Uani 1 1 d . . . H11 H -0.2787 0.6562 0.3918 0.027 Uiso 1 1 calc R . . C12 C 0.23969(16) 0.98685(6) 0.32788(5) 0.01579(18) Uani 1 1 d . . . H12 H 0.3491 0.9526 0.3485 0.019 Uiso 1 1 calc R . . C13 C 0.22735(16) 1.06105(6) 0.37039(5) 0.01597(18) Uani 1 1 d . . . H13 H 0.1590 1.0474 0.4146 0.019 Uiso 1 1 calc R . . C14 C 0.44772(18) 1.09099(7) 0.38667(6) 0.0223(2) Uani 1 1 d . . . C15 C 0.08783(18) 1.12254(6) 0.33702(6) 0.0219(2) Uani 1 1 d . . . H15A H 0.1674 1.1451 0.2986 0.026 Uiso 1 1 calc R . . H15B H -0.0398 1.0974 0.3180 0.026 Uiso 1 1 calc R . . C16 C 0.0162(2) 1.18704(7) 0.38362(7) 0.0307(3) Uani 1 1 d . . . H16A H -0.0592 1.1656 0.4228 0.046 Uiso 1 1 calc R . . H16B H -0.0787 1.2214 0.3586 0.046 Uiso 1 1 calc R . . H16C H 0.1404 1.2157 0.3994 0.046 Uiso 1 1 calc R . . C17 C 0.37439(17) 0.94392(6) 0.21997(5) 0.01764(19) Uani 1 1 d . . . C18 C 0.51358(18) 0.91835(6) 0.10615(5) 0.0205(2) Uani 1 1 d . . . C19 C 0.7295(2) 0.89124(8) 0.13060(6) 0.0299(3) Uani 1 1 d . . . H19A H 0.8126 0.9352 0.1463 0.045 Uiso 1 1 calc R . . H19B H 0.8043 0.8660 0.0931 0.045 Uiso 1 1 calc R . . H19C H 0.7110 0.8551 0.1681 0.045 Uiso 1 1 calc R . . C20 C 0.3667(3) 0.85229(9) 0.08997(7) 0.0371(3) Uani 1 1 d . . . H20A H 0.3548 0.8189 0.1298 0.056 Uiso 1 1 calc R . . H20B H 0.4241 0.8231 0.0516 0.056 Uiso 1 1 calc R . . H20C H 0.2261 0.8721 0.0780 0.056 Uiso 1 1 calc R . . C21 C 0.5389(2) 0.97171(8) 0.04557(6) 0.0293(3) Uani 1 1 d . . . H21A H 0.3999 0.9921 0.0326 0.044 Uiso 1 1 calc R . . H21B H 0.5995 0.9434 0.0072 0.044 Uiso 1 1 calc R . . H21C H 0.6336 1.0139 0.0578 0.044 Uiso 1 1 calc R . . F1 F 0.53940(15) 1.12632(6) 0.33436(5) 0.0481(3) Uani 1 1 d . . . F2 F 0.44400(14) 1.14223(5) 0.43745(5) 0.0383(2) Uani 1 1 d . . . F3 F 0.58209(14) 1.03651(5) 0.40676(6) 0.0434(2) Uani 1 1 d . . . H1N H 0.245(3) 1.0402(10) 0.2383(8) 0.028(4) Uiso 1 1 d . . . N1 N -0.02031(14) 0.89918(5) 0.38637(4) 0.01582(16) Uani 1 1 d . . . N2 N 0.29997(16) 1.00281(5) 0.25840(5) 0.01979(18) Uani 1 1 d . . . O5 O 0.00701(14) 0.83459(5) 0.48367(4) 0.02285(17) Uani 1 1 d . . . O1 O -0.10893(15) 0.95489(5) 0.28713(4) 0.02667(18) Uani 1 1 d . . . O2 O 0.41610(14) 0.96947(4) 0.15656(4) 0.02079(16) Uani 1 1 d . . . O3 O 0.29870(13) 0.89344(5) 0.44637(4) 0.02614(18) Uani 1 1 d . . . O4 O 0.40122(14) 0.87965(5) 0.24080(4) 0.02243(16) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0185(5) 0.0184(4) 0.0161(4) 0.0034(4) 0.0009(4) 0.0020(4) C2 0.0191(5) 0.0239(5) 0.0262(5) -0.0013(4) 0.0058(4) -0.0051(4) C3 0.0128(4) 0.0171(4) 0.0269(5) -0.0001(4) 0.0003(4) -0.0007(4) C4 0.0183(4) 0.0151(4) 0.0179(4) 0.0006(3) -0.0004(4) 0.0003(4) C5 0.0184(5) 0.0172(4) 0.0290(5) -0.0003(4) -0.0064(4) -0.0008(4) C6 0.0198(5) 0.0167(4) 0.0178(4) -0.0030(4) -0.0034(4) -0.0015(4) C7 0.0265(6) 0.0200(5) 0.0216(5) -0.0048(4) 0.0024(4) -0.0058(4) C8 0.0226(5) 0.0300(6) 0.0295(6) -0.0131(5) 0.0035(4) -0.0027(5) C9 0.0287(6) 0.0267(6) 0.0309(6) -0.0094(5) -0.0037(5) 0.0080(5) C10 0.0352(6) 0.0192(5) 0.0275(5) 0.0009(4) -0.0024(5) 0.0016(5) C11 0.0239(5) 0.0197(5) 0.0230(5) 0.0002(4) 0.0011(4) -0.0019(4) C12 0.0171(4) 0.0168(4) 0.0134(4) 0.0016(3) 0.0011(3) 0.0010(3) C13 0.0156(4) 0.0162(4) 0.0162(4) 0.0007(3) 0.0008(3) -0.0006(3) C14 0.0195(5) 0.0219(5) 0.0254(5) -0.0001(4) -0.0010(4) -0.0027(4) C15 0.0228(5) 0.0190(5) 0.0238(5) 0.0008(4) -0.0009(4) 0.0055(4) C16 0.0354(7) 0.0216(5) 0.0352(6) -0.0042(5) 0.0010(5) 0.0086(5) C17 0.0163(4) 0.0211(5) 0.0155(4) 0.0015(4) 0.0015(3) -0.0003(4) C18 0.0235(5) 0.0222(5) 0.0157(4) -0.0036(4) 0.0025(4) -0.0019(4) C19 0.0285(6) 0.0336(6) 0.0276(6) -0.0004(5) 0.0049(5) 0.0080(5) C20 0.0437(8) 0.0383(7) 0.0294(6) -0.0104(5) 0.0049(6) -0.0191(6) C21 0.0393(7) 0.0340(6) 0.0146(4) 0.0017(4) 0.0039(5) -0.0016(5) F1 0.0339(4) 0.0712(7) 0.0391(5) 0.0122(5) 0.0040(4) -0.0272(5) F2 0.0333(4) 0.0376(4) 0.0439(5) -0.0190(4) -0.0060(4) -0.0040(3) F3 0.0283(4) 0.0291(4) 0.0728(6) -0.0044(4) -0.0238(4) 0.0042(3) N1 0.0136(4) 0.0152(4) 0.0186(4) 0.0009(3) -0.0014(3) -0.0006(3) N2 0.0266(5) 0.0189(4) 0.0138(4) 0.0033(3) 0.0039(3) 0.0056(4) O5 0.0206(4) 0.0261(4) 0.0218(4) 0.0077(3) 0.0023(3) -0.0018(3) O1 0.0264(4) 0.0274(4) 0.0262(4) 0.0066(3) -0.0112(3) -0.0031(3) O2 0.0287(4) 0.0198(3) 0.0139(3) 0.0021(3) 0.0040(3) 0.0036(3) O3 0.0171(4) 0.0376(5) 0.0238(4) 0.0111(3) -0.0029(3) -0.0022(3) O4 0.0280(4) 0.0187(3) 0.0206(3) 0.0029(3) 0.0038(3) 0.0017(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 C1 O3 1.1972(14) . ? C1 O5 1.3465(13) . ? C1 N1 1.3929(13) . ? C2 O5 1.4530(15) . ? C2 C3 1.5321(16) . ? C3 N1 1.4801(13) . ? C3 C5 1.5316(15) . ? C4 O1 1.2072(13) . ? C4 N1 1.3974(13) . ? C4 C12 1.5377(15) . ? C5 C6 1.5051(15) . ? C6 C11 1.3963(15) . ? C6 C7 1.3988(16) . ? C7 C8 1.3832(18) . ? C8 C9 1.3893(19) . ? C9 C10 1.3879(19) . ? C10 C11 1.3894(17) . ? C12 N2 1.4463(13) . ? C12 C13 1.5468(14) . ? C13 C14 1.5189(15) . ? C13 C15 1.5373(15) . ? C14 F1 1.3326(14) . ? C14 F3 1.3353(14) . ? C14 F2 1.3428(14) . ? C15 C16 1.5228(16) . ? C17 O4 1.2092(14) . ? C17 O2 1.3513(12) . ? C17 N2 1.3618(14) . ? C18 O2 1.4705(13) . ? C18 C20 1.5154(17) . ? C18 C19 1.5198(18) . ? C18 C21 1.5227(16) . ? 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 O3 C1 O5 122.55(10) . . ? O3 C1 N1 128.46(10) . . ? O5 C1 N1 108.99(9) . . ? O5 C2 C3 105.41(8) . . ? N1 C3 C5 114.40(9) . . ? N1 C3 C2 100.44(8) . . ? C5 C3 C2 114.05(9) . . ? O1 C4 N1 119.60(10) . . ? O1 C4 C12 121.92(9) . . ? N1 C4 C12 118.47(9) . . ? C6 C5 C3 115.59(9) . . ? C11 C6 C7 118.20(10) . . ? C11 C6 C5 121.32(10) . . ? C7 C6 C5 120.46(10) . . ? C8 C7 C6 120.85(11) . . ? C7 C8 C9 120.58(12) . . ? C10 C9 C8 119.15(11) . . ? C9 C10 C11 120.42(11) . . ? C10 C11 C6 120.80(11) . . ? N2 C12 C4 110.91(8) . . ? N2 C12 C13 111.24(8) . . ? C4 C12 C13 108.88(8) . . ? C14 C13 C15 111.81(9) . . ? C14 C13 C12 110.97(9) . . ? C15 C13 C12 112.69(9) . . ? F1 C14 F3 106.56(11) . . ? F1 C14 F2 105.81(10) . . ? F3 C14 F2 105.54(10) . . ? F1 C14 C13 113.19(10) . . ? F3 C14 C13 113.33(9) . . ? F2 C14 C13 111.81(9) . . ? C16 C15 C13 115.57(10) . . ? O4 C17 O2 126.43(10) . . ? O4 C17 N2 124.34(10) . . ? O2 C17 N2 109.22(9) . . ? O2 C18 C20 110.53(10) . . ? O2 C18 C19 110.52(9) . . ? C20 C18 C19 112.06(11) . . ? O2 C18 C21 101.46(9) . . ? C20 C18 C21 111.58(10) . . ? C19 C18 C21 110.21(10) . . ? C1 N1 C4 128.21(9) . . ? C1 N1 C3 111.29(8) . . ? C4 N1 C3 120.41(9) . . ? C17 N2 C12 117.99(9) . . ? C1 O5 C2 110.55(9) . . ? C17 O2 C18 120.18(9) . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 30.60 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.270 _refine_diff_density_min -0.251 _refine_diff_density_rms 0.050 data_he3 _database_code_depnum_ccdc_archive 'CCDC 887851' #TrackingRef '5a.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H16 F3 N O3' _chemical_formula_weight 315.29 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 5.409(2) _cell_length_b 11.831(5) _cell_length_c 22.811(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1459.7(11) _cell_formula_units_Z 4 _cell_measurement_temperature 133(2) _cell_measurement_reflns_used 783 _cell_measurement_theta_min 3.6 _cell_measurement_theta_max 24.3 _exptl_crystal_description platelett _exptl_crystal_colour colourless _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.435 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 656 _exptl_absorpt_coefficient_mu 0.124 _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 133(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-AXS SMART CCD' _diffrn_measurement_method 'omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10619 _diffrn_reflns_av_R_equivalents 0.0627 _diffrn_reflns_av_sigmaI/netI 0.0366 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.79 _diffrn_reflns_theta_max 25.05 _reflns_number_total 1531 _reflns_number_gt 1164 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (BRUKER-AXS)' _computing_cell_refinement 'SAINT (BRUKER-AXS)' _computing_data_reduction 'SAINT (BRUKER-AXS)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0537P)^2^+1.0557P] 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 2(2) _refine_ls_number_reflns 1531 _refine_ls_number_parameters 200 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0723 _refine_ls_R_factor_gt 0.0472 _refine_ls_wR_factor_ref 0.1266 _refine_ls_wR_factor_gt 0.1143 _refine_ls_goodness_of_fit_ref 1.121 _refine_ls_restrained_S_all 1.121 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _chemical_absolute_configuration syn loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.3703(9) 0.4319(3) 0.98835(18) 0.0293(10) Uani 1 1 d . . . H1A H 0.4725 0.4285 1.0243 0.035 Uiso 1 1 calc R . . H1B H 0.2484 0.4938 0.9925 0.035 Uiso 1 1 calc R . . C2 C 0.5314(8) 0.4502(3) 0.93470(17) 0.0235(10) Uani 1 1 d . . . H2 H 0.6969 0.4804 0.9464 0.028 Uiso 1 1 calc R . . C3 C 0.4167(9) 0.5239(3) 0.88702(17) 0.0277(10) Uani 1 1 d . . . H3A H 0.5127 0.5141 0.8504 0.033 Uiso 1 1 calc R . . H3B H 0.2463 0.4972 0.8794 0.033 Uiso 1 1 calc R . . C4 C 0.4079(8) 0.6484(3) 0.90198(18) 0.0229(9) Uani 1 1 d . . . C5 C 0.5988(9) 0.7194(3) 0.88419(19) 0.0295(10) Uani 1 1 d . . . H5 H 0.7364 0.6895 0.8635 0.035 Uiso 1 1 calc R . . C6 C 0.5877(10) 0.8342(4) 0.8968(2) 0.0354(11) Uani 1 1 d . . . H6 H 0.7176 0.8825 0.8842 0.042 Uiso 1 1 calc R . . C7 C 0.3913(10) 0.8786(4) 0.9271(2) 0.0361(12) Uani 1 1 d . . . H7 H 0.3851 0.9573 0.9351 0.043 Uiso 1 1 calc R . . C8 C 0.2032(10) 0.8090(4) 0.9459(2) 0.0362(11) Uani 1 1 d . . . H8 H 0.0690 0.8391 0.9677 0.043 Uiso 1 1 calc R . . C9 C 0.2110(8) 0.6943(3) 0.93269(19) 0.0299(10) Uani 1 1 d . . . H9 H 0.0792 0.6467 0.9449 0.036 Uiso 1 1 calc R . . C10 C 0.3698(9) 0.2649(3) 0.9377(2) 0.0287(10) Uani 1 1 d . . . C11 C 0.7413(9) 0.3026(3) 0.87613(17) 0.0263(10) Uani 1 1 d . . . C12 C 0.7451(9) 0.1853(3) 0.85005(17) 0.0292(10) Uani 1 1 d . . . H12A H 0.8118 0.1312 0.8792 0.035 Uiso 1 1 calc R . . H12B H 0.5743 0.1618 0.8402 0.035 Uiso 1 1 calc R . . C13 C 0.9026(10) 0.1826(4) 0.79548(18) 0.0351(11) Uani 1 1 d . . . H13 H 1.0610 0.2229 0.8040 0.042 Uiso 1 1 calc R . . C14 C 0.9626(11) 0.0629(5) 0.7792(2) 0.0436(14) Uani 1 1 d . . . C15 C 0.7749(15) 0.2428(4) 0.7443(2) 0.0625(18) Uani 1 1 d . . . H15A H 0.7406 0.3214 0.7552 0.094 Uiso 1 1 calc R . . H15B H 0.6193 0.2042 0.7351 0.094 Uiso 1 1 calc R . . H15C H 0.8832 0.2413 0.7099 0.094 Uiso 1 1 calc R . . F1 F 1.0801(7) 0.0074(3) 0.82181(14) 0.0656(10) Uani 1 1 d . . . F2 F 1.1098(8) 0.0574(3) 0.73174(15) 0.0789(12) Uani 1 1 d . . . F3 F 0.7614(8) 0.0012(3) 0.76648(13) 0.0589(9) Uani 1 1 d . . . N1 N 0.5534(7) 0.3330(3) 0.91411(14) 0.0236(8) Uani 1 1 d . . . O1 O 0.2464(6) 0.3248(2) 0.97839(12) 0.0326(7) Uani 1 1 d . . . O2 O 0.3184(6) 0.1691(2) 0.92486(13) 0.0364(8) Uani 1 1 d . . . O3 O 0.8992(6) 0.3728(2) 0.86415(14) 0.0346(8) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.034(3) 0.021(2) 0.032(2) -0.0009(18) -0.001(2) 0.000(2) C2 0.029(2) 0.016(2) 0.025(2) 0.0002(17) 0.002(2) -0.0050(18) C3 0.029(2) 0.024(2) 0.030(2) 0.0010(17) 0.000(2) -0.007(2) C4 0.023(2) 0.021(2) 0.025(2) 0.0045(16) -0.003(2) -0.0024(18) C5 0.029(3) 0.023(2) 0.036(2) 0.0044(18) -0.002(2) -0.004(2) C6 0.034(3) 0.027(2) 0.046(3) 0.009(2) -0.005(3) -0.006(2) C7 0.040(3) 0.022(2) 0.047(3) 0.000(2) -0.013(3) 0.006(2) C8 0.035(3) 0.030(2) 0.044(3) 0.000(2) -0.005(2) 0.007(2) C9 0.021(2) 0.030(2) 0.039(2) 0.006(2) 0.000(2) 0.000(2) C10 0.029(2) 0.025(2) 0.032(2) 0.0060(19) -0.002(2) -0.003(2) C11 0.027(2) 0.026(2) 0.025(2) 0.0009(17) 0.000(2) -0.003(2) C12 0.033(2) 0.025(2) 0.030(2) -0.0015(18) -0.003(2) 0.004(2) C13 0.042(3) 0.033(2) 0.030(2) -0.005(2) 0.002(2) -0.004(3) C14 0.051(3) 0.044(3) 0.036(3) -0.012(2) 0.010(3) 0.000(3) C15 0.105(6) 0.048(3) 0.034(3) 0.003(2) -0.001(4) 0.006(4) F1 0.077(2) 0.0516(19) 0.068(2) -0.0101(17) -0.008(2) 0.026(2) F2 0.105(3) 0.057(2) 0.075(2) -0.0208(17) 0.049(2) -0.002(2) F3 0.076(2) 0.0418(16) 0.0589(18) -0.0152(14) -0.0005(19) -0.0077(18) N1 0.0251(19) 0.0158(16) 0.0298(19) 0.0007(15) 0.0040(16) -0.0037(16) O1 0.0347(18) 0.0239(15) 0.0390(16) 0.0036(13) 0.0072(17) -0.0038(16) O2 0.037(2) 0.0209(15) 0.0507(19) -0.0010(14) 0.0031(16) -0.0089(14) O3 0.0282(18) 0.0306(16) 0.0449(19) -0.0046(14) 0.0061(17) -0.0086(15) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.450(5) . ? C1 C2 1.518(6) . ? C2 N1 1.470(5) . ? C2 C3 1.525(6) . ? C3 C4 1.513(5) . ? C4 C9 1.386(6) . ? C4 C5 1.392(6) . ? C5 C6 1.389(6) . ? C6 C7 1.372(7) . ? C7 C8 1.377(7) . ? C8 C9 1.390(6) . ? C10 O2 1.204(5) . ? C10 O1 1.345(5) . ? C10 N1 1.387(5) . ? C11 O3 1.222(5) . ? C11 N1 1.383(5) . ? C11 C12 1.510(5) . ? C12 C13 1.509(6) . ? C13 C14 1.501(7) . ? C13 C15 1.531(7) . ? C14 F1 1.334(6) . ? C14 F3 1.342(6) . ? C14 F2 1.346(6) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 C2 105.3(3) . . ? N1 C2 C1 99.7(3) . . ? N1 C2 C3 110.1(3) . . ? C1 C2 C3 115.0(4) . . ? C4 C3 C2 114.1(3) . . ? C9 C4 C5 118.7(4) . . ? C9 C4 C3 121.4(4) . . ? C5 C4 C3 119.9(4) . . ? C6 C5 C4 119.9(5) . . ? C7 C6 C5 120.8(5) . . ? C6 C7 C8 120.0(4) . . ? C7 C8 C9 119.6(5) . . ? C4 C9 C8 121.0(4) . . ? O2 C10 O1 123.3(4) . . ? O2 C10 N1 128.1(4) . . ? O1 C10 N1 108.5(3) . . ? O3 C11 N1 118.5(4) . . ? O3 C11 C12 121.8(4) . . ? N1 C11 C12 119.7(4) . . ? C13 C12 C11 110.6(4) . . ? C14 C13 C12 110.2(4) . . ? C14 C13 C15 110.4(4) . . ? C12 C13 C15 111.4(5) . . ? F1 C14 F3 106.1(5) . . ? F1 C14 F2 106.3(5) . . ? F3 C14 F2 106.2(4) . . ? F1 C14 C13 112.8(4) . . ? F3 C14 C13 113.1(5) . . ? F2 C14 C13 111.9(4) . . ? C11 N1 C10 128.2(4) . . ? C11 N1 C2 120.3(3) . . ? C10 N1 C2 111.5(3) . . ? C10 O1 C1 109.8(3) . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 25.05 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.252 _refine_diff_density_min -0.241 _refine_diff_density_rms 0.059