# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Chun-Jiang Wang' _publ_contact_author_email cjwang@whu.edu.cn loop_ _publ_author_name 'Chun-Jiang Wang' 'Qin-Hua Li Min-Chao Tong' 'Hai-Yan Tao' data_110307ltl_0m _database_code_depnum_ccdc_archive 'CCDC 827404' #TrackingRef '- 827404_0m.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_absolute_configuration 7S,8R,9S.10R _chemical_formula_sum 'C23 H21 Cl F3 N O5' _chemical_formula_weight 483.86 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' Cl Cl 0.1484 0.1585 '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 8.6745(12) _cell_length_b 13.3919(18) _cell_length_c 19.262(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2237.6(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour ? _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.436 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1000 _exptl_absorpt_coefficient_mu 0.231 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9297 _exptl_absorpt_correction_T_max 0.9531 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12954 _diffrn_reflns_av_R_equivalents 0.0219 _diffrn_reflns_av_sigmaI/netI 0.0265 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.58 _diffrn_reflns_theta_max 26.49 _reflns_number_total 4613 _reflns_number_gt 3670 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _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^)+(0.0366P)^2^+0.3021P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0032(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.08(7) _refine_ls_number_reflns 4613 _refine_ls_number_parameters 301 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0500 _refine_ls_R_factor_gt 0.0353 _refine_ls_wR_factor_ref 0.0845 _refine_ls_wR_factor_gt 0.0775 _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_restrained_S_all 1.025 _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 C1 C 0.8060(3) 0.66515(16) 0.79507(11) 0.0539(6) Uani 1 1 d . . . C2 C 0.8531(3) 0.62126(16) 0.73467(12) 0.0547(6) Uani 1 1 d . . . H2 H 0.9515 0.5942 0.7311 0.066 Uiso 1 1 calc R . . C3 C 0.7523(3) 0.61755(16) 0.67870(11) 0.0493(5) Uani 1 1 d . . . H3 H 0.7838 0.5886 0.6372 0.059 Uiso 1 1 calc R . . C4 C 0.6060(2) 0.65638(14) 0.68432(9) 0.0418(5) Uani 1 1 d . . . C5 C 0.5620(3) 0.69944(16) 0.74635(10) 0.0520(5) Uani 1 1 d . . . H5 H 0.4634 0.7261 0.7505 0.062 Uiso 1 1 calc R . . C6 C 0.6612(3) 0.70370(16) 0.80234(11) 0.0572(6) Uani 1 1 d . . . H6 H 0.6300 0.7322 0.8441 0.069 Uiso 1 1 calc R . . C7 C 0.4911(2) 0.65505(14) 0.62483(9) 0.0405(4) Uani 1 1 d . . . H7 H 0.4580 0.7241 0.6169 0.049 Uiso 1 1 calc R . . C8 C 0.3445(2) 0.59217(15) 0.63839(10) 0.0424(4) Uani 1 1 d . . . H8 H 0.2621 0.6355 0.6557 0.051 Uiso 1 1 calc R . . C9 C 0.3034(2) 0.55505(15) 0.56517(10) 0.0431(5) Uani 1 1 d . . . H9 H 0.2646 0.6142 0.5408 0.052 Uiso 1 1 calc R . . C10 C 0.4596(2) 0.53274(14) 0.53133(9) 0.0407(4) Uani 1 1 d . . . H10 H 0.4481 0.5425 0.4812 0.049 Uiso 1 1 calc R . . C11 C 0.6320(3) 0.68034(14) 0.51750(10) 0.0475(5) Uani 1 1 d . . . C12 C 0.6658(3) 0.65086(14) 0.44423(10) 0.0451(5) Uani 1 1 d . . . C13 C 0.7759(3) 0.58086(17) 0.42847(13) 0.0643(6) Uani 1 1 d . . . H13 H 0.8264 0.5466 0.4638 0.077 Uiso 1 1 calc R . . C14 C 0.8115(3) 0.5615(2) 0.35932(17) 0.0804(9) Uani 1 1 d . . . H14 H 0.8861 0.5142 0.3485 0.096 Uiso 1 1 calc R . . C15 C 0.7385(4) 0.6110(2) 0.30760(14) 0.0738(8) Uani 1 1 d . . . H15 H 0.7644 0.5981 0.2616 0.089 Uiso 1 1 calc R . . C16 C 0.6280(3) 0.67925(19) 0.32249(11) 0.0668(7) Uani 1 1 d . . . H16 H 0.5770 0.7121 0.2867 0.080 Uiso 1 1 calc R . . C17 C 0.5907(3) 0.70024(17) 0.39111(11) 0.0557(6) Uani 1 1 d . . . H17 H 0.5154 0.7474 0.4013 0.067 Uiso 1 1 calc R . . C18 C 0.3719(2) 0.50783(16) 0.68949(10) 0.0458(5) Uani 1 1 d . . . C19 C 0.2774(4) 0.4308(2) 0.79139(12) 0.0784(8) Uani 1 1 d . . . H19A H 0.2080 0.3770 0.7786 0.094 Uiso 1 1 calc R . . H19B H 0.3814 0.4043 0.7931 0.094 Uiso 1 1 calc R . . C20 C 0.2359(5) 0.4696(3) 0.85688(15) 0.1126(13) Uani 1 1 d . . . H20A H 0.2983 0.5269 0.8671 0.169 Uiso 1 1 calc R . . H20B H 0.2519 0.4195 0.8918 0.169 Uiso 1 1 calc R . . H20C H 0.1292 0.4886 0.8563 0.169 Uiso 1 1 calc R . . C21 C 0.1728(3) 0.48091(18) 0.56259(12) 0.0568(6) Uani 1 1 d . . . C22 C 0.5272(2) 0.42915(15) 0.54272(10) 0.0460(5) Uani 1 1 d . . . C23 C 0.7470(4) 0.3344(2) 0.56539(19) 0.0955(10) Uani 1 1 d . . . H23A H 0.6904 0.2959 0.5988 0.143 Uiso 1 1 calc R . . H23B H 0.8513 0.3426 0.5810 0.143 Uiso 1 1 calc R . . H23C H 0.7467 0.3004 0.5215 0.143 Uiso 1 1 calc R . . Cl1 Cl 0.93225(9) 0.66989(5) 0.86545(4) 0.0841(2) Uani 1 1 d . . . F1 F 0.14798(18) 0.44664(11) 0.49896(7) 0.0801(4) Uani 1 1 d . . . F2 F 0.18464(16) 0.40296(10) 0.60419(7) 0.0701(4) Uani 1 1 d . . . F3 F 0.04131(16) 0.52782(12) 0.58123(9) 0.0855(5) Uani 1 1 d . . . N1 N 0.55186(19) 0.61640(11) 0.55838(7) 0.0392(4) Uani 1 1 d . . . O1 O 0.6773(2) 0.76051(12) 0.54005(8) 0.0761(6) Uani 1 1 d . . . O2 O 0.47186(18) 0.44716(11) 0.68434(7) 0.0568(4) Uani 1 1 d . . . O3 O 0.26834(19) 0.51115(13) 0.74002(8) 0.0645(4) Uani 1 1 d . . . O4 O 0.67592(18) 0.43094(10) 0.55758(8) 0.0578(4) Uani 1 1 d . . . O5 O 0.45310(19) 0.35518(11) 0.53343(9) 0.0667(5) 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 0.0629(15) 0.0467(12) 0.0521(12) 0.0013(10) -0.0158(11) -0.0023(11) C2 0.0464(13) 0.0539(13) 0.0638(14) 0.0016(11) -0.0041(11) 0.0017(11) C3 0.0490(13) 0.0508(12) 0.0482(12) -0.0028(10) 0.0022(10) 0.0024(10) C4 0.0479(12) 0.0373(10) 0.0402(10) 0.0047(8) 0.0015(9) -0.0027(9) C5 0.0548(13) 0.0548(13) 0.0464(11) -0.0033(10) 0.0002(10) 0.0098(11) C6 0.0714(16) 0.0545(13) 0.0457(12) -0.0084(10) -0.0040(11) 0.0069(12) C7 0.0473(12) 0.0360(10) 0.0382(10) 0.0028(8) 0.0030(8) 0.0035(9) C8 0.0378(11) 0.0460(11) 0.0433(10) 0.0070(9) 0.0028(9) 0.0056(9) C9 0.0382(11) 0.0464(10) 0.0447(10) 0.0098(9) -0.0031(9) 0.0019(9) C10 0.0424(11) 0.0410(11) 0.0386(10) 0.0039(8) 0.0001(8) -0.0069(9) C11 0.0587(14) 0.0392(11) 0.0446(11) 0.0036(9) 0.0040(10) -0.0091(10) C12 0.0501(12) 0.0399(10) 0.0454(11) 0.0055(9) 0.0078(10) -0.0104(10) C13 0.0655(16) 0.0554(14) 0.0719(15) 0.0047(12) 0.0079(13) 0.0024(12) C14 0.0792(19) 0.0602(15) 0.102(2) -0.0160(16) 0.0401(18) -0.0016(15) C15 0.101(2) 0.0634(16) 0.0570(15) -0.0137(13) 0.0262(15) -0.0281(16) C16 0.0866(19) 0.0683(16) 0.0454(13) -0.0015(11) -0.0033(12) -0.0114(15) C17 0.0596(15) 0.0566(13) 0.0510(12) 0.0000(10) 0.0036(11) -0.0012(11) C18 0.0413(12) 0.0499(12) 0.0462(11) 0.0061(9) 0.0030(9) -0.0020(10) C19 0.103(2) 0.0734(17) 0.0588(15) 0.0263(13) 0.0220(15) 0.0025(16) C20 0.158(4) 0.111(3) 0.0692(18) 0.0249(18) 0.026(2) 0.040(3) C21 0.0403(12) 0.0698(14) 0.0604(14) 0.0074(13) -0.0029(11) -0.0024(11) C22 0.0449(12) 0.0448(12) 0.0484(11) 0.0016(9) 0.0063(9) -0.0057(10) C23 0.0698(18) 0.0571(15) 0.160(3) 0.0145(19) 0.003(2) 0.0162(15) Cl1 0.0944(5) 0.0795(5) 0.0784(4) -0.0116(4) -0.0417(4) 0.0094(4) F1 0.0711(10) 0.0999(11) 0.0694(9) -0.0023(8) -0.0121(8) -0.0302(9) F2 0.0620(9) 0.0667(8) 0.0815(9) 0.0214(7) -0.0002(7) -0.0206(7) F3 0.0363(8) 0.0996(11) 0.1205(12) 0.0022(10) 0.0044(8) 0.0015(8) N1 0.0440(9) 0.0364(8) 0.0372(8) 0.0027(7) 0.0044(8) -0.0043(7) O1 0.1225(17) 0.0543(9) 0.0517(9) -0.0045(7) 0.0155(10) -0.0391(11) O2 0.0546(9) 0.0532(9) 0.0625(9) 0.0175(7) 0.0026(8) 0.0069(8) O3 0.0668(10) 0.0759(10) 0.0509(8) 0.0171(8) 0.0184(8) 0.0058(9) O4 0.0463(9) 0.0461(8) 0.0812(10) 0.0080(8) 0.0016(8) 0.0039(7) O5 0.0601(10) 0.0448(9) 0.0951(12) -0.0084(8) 0.0087(9) -0.0099(8) _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 C6 1.366(3) . ? C1 C2 1.366(3) . ? C1 Cl1 1.744(2) . ? C2 C3 1.389(3) . ? C2 H2 0.9300 . ? C3 C4 1.375(3) . ? C3 H3 0.9300 . ? C4 C5 1.381(3) . ? C4 C7 1.519(3) . ? C5 C6 1.381(3) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 N1 1.478(2) . ? C7 C8 1.547(3) . ? C7 H7 0.9800 . ? C8 C18 1.517(3) . ? C8 C9 1.537(3) . ? C8 H8 0.9800 . ? C9 C21 1.507(3) . ? C9 C10 1.533(3) . ? C9 H9 0.9800 . ? C10 N1 1.472(2) . ? C10 C22 1.522(3) . ? C10 H10 0.9800 . ? C11 O1 1.223(2) . ? C11 N1 1.355(2) . ? C11 C12 1.494(3) . ? C12 C13 1.372(3) . ? C12 C17 1.381(3) . ? C13 C14 1.392(4) . ? C13 H13 0.9300 . ? C14 C15 1.353(4) . ? C14 H14 0.9300 . ? C15 C16 1.355(4) . ? C15 H15 0.9300 . ? C16 C17 1.389(3) . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? C18 O2 1.192(2) . ? C18 O3 1.325(2) . ? C19 C20 1.411(4) . ? C19 O3 1.464(3) . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C21 F2 1.320(3) . ? C21 F1 1.326(3) . ? C21 F3 1.351(3) . ? C22 O5 1.194(2) . ? C22 O4 1.322(3) . ? C23 O4 1.440(3) . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 C1 C2 121.7(2) . . ? C6 C1 Cl1 118.96(18) . . ? C2 C1 Cl1 119.35(19) . . ? C1 C2 C3 119.2(2) . . ? C1 C2 H2 120.4 . . ? C3 C2 H2 120.4 . . ? C4 C3 C2 120.41(19) . . ? C4 C3 H3 119.8 . . ? C2 C3 H3 119.8 . . ? C3 C4 C5 118.79(19) . . ? C3 C4 C7 122.78(17) . . ? C5 C4 C7 118.43(18) . . ? C4 C5 C6 121.4(2) . . ? C4 C5 H5 119.3 . . ? C6 C5 H5 119.3 . . ? C1 C6 C5 118.5(2) . . ? C1 C6 H6 120.7 . . ? C5 C6 H6 120.7 . . ? N1 C7 C4 115.06(16) . . ? N1 C7 C8 104.39(15) . . ? C4 C7 C8 114.73(15) . . ? N1 C7 H7 107.4 . . ? C4 C7 H7 107.4 . . ? C8 C7 H7 107.4 . . ? C18 C8 C9 113.01(16) . . ? C18 C8 C7 112.71(16) . . ? C9 C8 C7 102.22(15) . . ? C18 C8 H8 109.6 . . ? C9 C8 H8 109.6 . . ? C7 C8 H8 109.6 . . ? C21 C9 C10 121.46(17) . . ? C21 C9 C8 114.68(17) . . ? C10 C9 C8 104.38(15) . . ? C21 C9 H9 104.9 . . ? C10 C9 H9 104.9 . . ? C8 C9 H9 104.9 . . ? N1 C10 C22 115.67(16) . . ? N1 C10 C9 100.46(14) . . ? C22 C10 C9 117.18(16) . . ? N1 C10 H10 107.6 . . ? C22 C10 H10 107.6 . . ? C9 C10 H10 107.6 . . ? O1 C11 N1 120.87(18) . . ? O1 C11 C12 120.30(18) . . ? N1 C11 C12 118.83(17) . . ? C13 C12 C17 119.4(2) . . ? C13 C12 C11 121.7(2) . . ? C17 C12 C11 118.73(19) . . ? C12 C13 C14 119.5(2) . . ? C12 C13 H13 120.2 . . ? C14 C13 H13 120.2 . . ? C15 C14 C13 120.6(3) . . ? C15 C14 H14 119.7 . . ? C13 C14 H14 119.7 . . ? C14 C15 C16 120.3(2) . . ? C14 C15 H15 119.8 . . ? C16 C15 H15 119.8 . . ? C15 C16 C17 120.2(2) . . ? C15 C16 H16 119.9 . . ? C17 C16 H16 119.9 . . ? C12 C17 C16 119.9(2) . . ? C12 C17 H17 120.1 . . ? C16 C17 H17 120.1 . . ? O2 C18 O3 125.23(19) . . ? O2 C18 C8 124.57(18) . . ? O3 C18 C8 110.20(18) . . ? C20 C19 O3 108.7(2) . . ? C20 C19 H19A 110.0 . . ? O3 C19 H19A 110.0 . . ? C20 C19 H19B 110.0 . . ? O3 C19 H19B 110.0 . . ? H19A C19 H19B 108.3 . . ? C19 C20 H20A 109.5 . . ? C19 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C19 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? F2 C21 F1 107.46(19) . . ? F2 C21 F3 105.78(19) . . ? F1 C21 F3 105.62(19) . . ? F2 C21 C9 116.26(18) . . ? F1 C21 C9 112.37(18) . . ? F3 C21 C9 108.65(19) . . ? O5 C22 O4 124.9(2) . . ? O5 C22 C10 121.81(19) . . ? O4 C22 C10 113.00(17) . . ? O4 C23 H23A 109.5 . . ? O4 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? O4 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C11 N1 C10 123.65(15) . . ? C11 N1 C7 117.70(15) . . ? C10 N1 C7 112.29(15) . . ? C18 O3 C19 115.80(18) . . ? C22 O4 C23 115.11(19) . . ? 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 C6 C1 C2 C3 1.4(3) . . . . ? Cl1 C1 C2 C3 179.97(17) . . . . ? C1 C2 C3 C4 -0.9(3) . . . . ? C2 C3 C4 C5 0.3(3) . . . . ? C2 C3 C4 C7 179.62(18) . . . . ? C3 C4 C5 C6 -0.3(3) . . . . ? C7 C4 C5 C6 -179.58(19) . . . . ? C2 C1 C6 C5 -1.3(4) . . . . ? Cl1 C1 C6 C5 -179.88(17) . . . . ? C4 C5 C6 C1 0.7(3) . . . . ? C3 C4 C7 N1 -4.8(3) . . . . ? C5 C4 C7 N1 174.47(17) . . . . ? C3 C4 C7 C8 116.3(2) . . . . ? C5 C4 C7 C8 -64.4(2) . . . . ? N1 C7 C8 C18 99.62(18) . . . . ? C4 C7 C8 C18 -27.2(2) . . . . ? N1 C7 C8 C9 -21.98(18) . . . . ? C4 C7 C8 C9 -148.83(16) . . . . ? C18 C8 C9 C21 52.0(2) . . . . ? C7 C8 C9 C21 173.44(17) . . . . ? C18 C8 C9 C10 -83.26(19) . . . . ? C7 C8 C9 C10 38.15(18) . . . . ? C21 C9 C10 N1 -170.31(17) . . . . ? C8 C9 C10 N1 -38.84(17) . . . . ? C21 C9 C10 C22 -44.2(3) . . . . ? C8 C9 C10 C22 87.32(19) . . . . ? O1 C11 C12 C13 105.0(3) . . . . ? N1 C11 C12 C13 -74.5(3) . . . . ? O1 C11 C12 C17 -70.8(3) . . . . ? N1 C11 C12 C17 109.7(2) . . . . ? C17 C12 C13 C14 0.7(3) . . . . ? C11 C12 C13 C14 -175.0(2) . . . . ? C12 C13 C14 C15 -0.1(4) . . . . ? C13 C14 C15 C16 -0.9(4) . . . . ? C14 C15 C16 C17 1.2(4) . . . . ? C13 C12 C17 C16 -0.5(3) . . . . ? C11 C12 C17 C16 175.4(2) . . . . ? C15 C16 C17 C12 -0.5(4) . . . . ? C9 C8 C18 O2 62.5(3) . . . . ? C7 C8 C18 O2 -52.8(3) . . . . ? C9 C8 C18 O3 -117.02(19) . . . . ? C7 C8 C18 O3 127.71(19) . . . . ? C10 C9 C21 F2 75.2(3) . . . . ? C8 C9 C21 F2 -51.8(3) . . . . ? C10 C9 C21 F1 -49.2(3) . . . . ? C8 C9 C21 F1 -176.18(18) . . . . ? C10 C9 C21 F3 -165.69(17) . . . . ? C8 C9 C21 F3 67.3(2) . . . . ? N1 C10 C22 O5 167.75(19) . . . . ? C9 C10 C22 O5 49.5(3) . . . . ? N1 C10 C22 O4 -17.7(2) . . . . ? C9 C10 C22 O4 -135.95(18) . . . . ? O1 C11 N1 C10 163.2(2) . . . . ? C12 C11 N1 C10 -17.3(3) . . . . ? O1 C11 N1 C7 13.4(3) . . . . ? C12 C11 N1 C7 -167.13(18) . . . . ? C22 C10 N1 C11 107.2(2) . . . . ? C9 C10 N1 C11 -125.62(19) . . . . ? C22 C10 N1 C7 -101.58(19) . . . . ? C9 C10 N1 C7 25.59(18) . . . . ? C4 C7 N1 C11 -82.6(2) . . . . ? C8 C7 N1 C11 150.71(17) . . . . ? C4 C7 N1 C10 124.28(17) . . . . ? C8 C7 N1 C10 -2.36(19) . . . . ? O2 C18 O3 C19 -2.2(3) . . . . ? C8 C18 O3 C19 177.29(19) . . . . ? C20 C19 O3 C18 145.5(3) . . . . ? O5 C22 O4 C23 -2.7(3) . . . . ? C10 C22 O4 C23 -177.0(2) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.49 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.173 _refine_diff_density_min -0.181 _refine_diff_density_rms 0.029 # Attachment '- 827405_0m.cif' data_110418lqh_0m _database_code_depnum_ccdc_archive 'CCDC 827405' #TrackingRef '- 827405_0m.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_absolute_configuration 7S,8S,12S,14R,38R,41S,43S,30S _chemical_formula_sum 'C23 H21 Cl F3 N O5' _chemical_formula_weight 483.86 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' Cl Cl 0.1484 0.1585 '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 14.7950(17) _cell_length_b 15.6582(17) _cell_length_c 20.390(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4723.6(9) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour ? _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.361 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2000 _exptl_absorpt_coefficient_mu 0.219 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9413 _exptl_absorpt_correction_T_max 0.9514 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 26602 _diffrn_reflns_av_R_equivalents 0.0287 _diffrn_reflns_av_sigmaI/netI 0.0345 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.14 _diffrn_reflns_theta_max 26.00 _reflns_number_total 9253 _reflns_number_gt 6467 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _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^)+(0.0322P)^2^+0.9061P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0038(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.02(6) _refine_ls_number_reflns 9253 _refine_ls_number_parameters 600 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0700 _refine_ls_R_factor_gt 0.0422 _refine_ls_wR_factor_ref 0.0945 _refine_ls_wR_factor_gt 0.0827 _refine_ls_goodness_of_fit_ref 1.015 _refine_ls_restrained_S_all 1.015 _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 C1 C -0.0493(2) 0.63914(18) 1.11336(14) 0.0710(8) Uani 1 1 d . . . C2 C 0.0387(3) 0.65836(19) 1.10263(15) 0.0792(9) Uani 1 1 d . . . H2 H 0.0640 0.7072 1.1211 0.095 Uiso 1 1 calc R . . C3 C 0.0909(2) 0.60474(17) 1.06395(13) 0.0642(7) Uani 1 1 d . . . H3 H 0.1517 0.6169 1.0573 0.077 Uiso 1 1 calc R . . C4 C 0.05311(17) 0.53350(14) 1.03530(11) 0.0477(6) Uani 1 1 d . . . C5 C -0.03671(18) 0.51716(16) 1.04556(13) 0.0572(6) Uani 1 1 d . . . H5 H -0.0633 0.4701 1.0255 0.069 Uiso 1 1 calc R . . C6 C -0.0886(2) 0.56933(19) 1.08508(14) 0.0702(8) Uani 1 1 d . . . H6 H -0.1493 0.5571 1.0923 0.084 Uiso 1 1 calc R . . C7 C 0.10983(16) 0.48106(14) 0.98911(11) 0.0472(6) Uani 1 1 d . . . H7 H 0.1738 0.4928 0.9976 0.057 Uiso 1 1 calc R . . C8 C 0.08854(17) 0.50144(15) 0.91654(11) 0.0519(6) Uani 1 1 d . . . H8 H 0.0236 0.5115 0.9110 0.062 Uiso 1 1 calc R . . C9 C 0.1412(2) 0.5792(2) 0.89478(14) 0.0716(8) Uani 1 1 d . . . C10 C 0.1289(4) 0.7294(3) 0.8789(3) 0.155(2) Uani 1 1 d . . . H10A H 0.1033 0.7712 0.9087 0.186 Uiso 1 1 calc R . . H10B H 0.1934 0.7261 0.8871 0.186 Uiso 1 1 calc R . . C11 C 0.1141(6) 0.7541(3) 0.8162(3) 0.217(4) Uani 1 1 d . . . H11A H 0.1369 0.7113 0.7868 0.326 Uiso 1 1 calc R . . H11B H 0.1447 0.8072 0.8081 0.326 Uiso 1 1 calc R . . H11C H 0.0505 0.7614 0.8091 0.326 Uiso 1 1 calc R . . C12 C 0.11603(17) 0.41943(16) 0.88131(11) 0.0543(6) Uani 1 1 d . . . H12 H 0.1822 0.4172 0.8809 0.065 Uiso 1 1 calc R . . C13 C 0.0847(2) 0.4129(2) 0.81167(14) 0.0728(8) Uani 1 1 d . . . C14 C 0.08297(16) 0.34897(15) 0.92729(11) 0.0485(6) Uani 1 1 d . . . H14 H 0.1222 0.2988 0.9234 0.058 Uiso 1 1 calc R . . C15 C -0.01532(18) 0.32264(16) 0.91822(12) 0.0533(6) Uani 1 1 d . . . C16 C -0.1121(2) 0.2221(2) 0.87049(16) 0.0840(9) Uani 1 1 d . . . H16A H -0.1428 0.2118 0.9112 0.126 Uiso 1 1 calc R . . H16B H -0.1101 0.1703 0.8454 0.126 Uiso 1 1 calc R . . H16C H -0.1439 0.2651 0.8462 0.126 Uiso 1 1 calc R . . C17 C 0.08217(17) 0.33692(16) 1.04452(13) 0.0522(6) Uani 1 1 d . . . C18 C 0.10534(18) 0.36663(15) 1.11119(12) 0.0524(6) Uani 1 1 d . . . C19 C 0.18390(19) 0.40969(18) 1.12500(13) 0.0649(7) Uani 1 1 d . . . H19 H 0.2218 0.4266 1.0910 0.078 Uiso 1 1 calc R . . C20 C 0.2068(2) 0.4279(2) 1.18901(15) 0.0821(9) Uani 1 1 d . . . H20 H 0.2608 0.4558 1.1982 0.099 Uiso 1 1 calc R . . C21 C 0.1499(3) 0.4051(2) 1.23900(15) 0.0881(11) Uani 1 1 d . . . H21 H 0.1654 0.4176 1.2822 0.106 Uiso 1 1 calc R . . C22 C 0.0706(3) 0.3641(2) 1.22565(16) 0.0900(11) Uani 1 1 d . . . H22 H 0.0310 0.3504 1.2595 0.108 Uiso 1 1 calc R . . C23 C 0.0493(2) 0.34305(19) 1.16193(14) 0.0741(8) Uani 1 1 d . . . H23 H -0.0034 0.3127 1.1531 0.089 Uiso 1 1 calc R . . C24 C 0.3285(2) 0.71625(18) 1.07166(16) 0.0730(8) Uani 1 1 d . . . C25 C 0.3575(3) 0.7046(2) 1.00985(17) 0.0933(11) Uani 1 1 d . . . H25 H 0.3460 0.7456 0.9779 0.112 Uiso 1 1 calc R . . C26 C 0.4050(2) 0.63075(19) 0.99390(15) 0.0821(10) Uani 1 1 d . . . H26 H 0.4253 0.6227 0.9512 0.099 Uiso 1 1 calc R . . C27 C 0.42209(16) 0.56984(16) 1.04037(12) 0.0513(6) Uani 1 1 d . . . C28 C 0.3895(2) 0.58389(19) 1.10242(13) 0.0737(8) Uani 1 1 d . . . H28 H 0.3991 0.5428 1.1346 0.088 Uiso 1 1 calc R . . C29 C 0.3431(2) 0.6570(2) 1.11840(16) 0.0856(10) Uani 1 1 d . . . H29 H 0.3221 0.6654 1.1609 0.103 Uiso 1 1 calc R . . C30 C 0.47510(16) 0.48979(15) 1.02648(12) 0.0501(6) Uani 1 1 d . . . H30 H 0.4602 0.4478 1.0605 0.060 Uiso 1 1 calc R . . C38 C 0.54135(16) 0.42440(15) 0.92909(12) 0.0512(6) Uani 1 1 d . . . H38 H 0.5349 0.3665 0.9114 0.061 Uiso 1 1 calc R . . C39 C 0.56598(19) 0.4864(2) 0.87456(15) 0.0670(8) Uani 1 1 d . . . C40 C 0.6437(3) 0.4976(3) 0.77382(19) 0.1355(18) Uani 1 1 d . . . H40A H 0.5937 0.5209 0.7498 0.203 Uiso 1 1 calc R . . H40B H 0.6800 0.4633 0.7450 0.203 Uiso 1 1 calc R . . H40C H 0.6798 0.5432 0.7913 0.203 Uiso 1 1 calc R . . C41 C 0.60815(15) 0.42432(16) 0.98644(13) 0.0537(6) Uani 1 1 d . . . H41 H 0.5948 0.3737 1.0130 0.064 Uiso 1 1 calc R . . C42 C 0.70634(19) 0.4205(2) 0.96924(17) 0.0714(8) Uani 1 1 d . . . C43 C 0.57826(16) 0.50185(16) 1.02624(13) 0.0567(7) Uani 1 1 d . . . H43 H 0.5927 0.5536 1.0013 0.068 Uiso 1 1 calc R . . C44 C 0.6199(2) 0.50899(19) 1.09305(16) 0.0682(8) Uani 1 1 d . . . C45 C 0.6284(3) 0.4510(3) 1.19948(17) 0.0975(11) Uani 1 1 d . . . H45A H 0.6931 0.4409 1.1976 0.117 Uiso 1 1 calc R . . H45B H 0.6182 0.5065 1.2194 0.117 Uiso 1 1 calc R . . C46 C 0.5847(4) 0.3847(3) 1.23806(19) 0.1311(17) Uani 1 1 d . . . H46A H 0.5208 0.3949 1.2392 0.197 Uiso 1 1 calc R . . H46B H 0.6083 0.3855 1.2819 0.197 Uiso 1 1 calc R . . H46C H 0.5963 0.3300 1.2185 0.197 Uiso 1 1 calc R . . C47 C 0.37806(17) 0.40757(16) 0.95452(13) 0.0523(6) Uani 1 1 d . . . C48 C 0.36324(16) 0.35842(17) 0.89267(13) 0.0543(6) Uani 1 1 d . . . C49 C 0.3293(2) 0.27687(19) 0.89871(16) 0.0756(9) Uani 1 1 d . . . H49 H 0.3195 0.2533 0.9400 0.091 Uiso 1 1 calc R . . C50 C 0.3099(3) 0.2306(2) 0.8431(2) 0.1020(12) Uani 1 1 d . . . H50 H 0.2863 0.1757 0.8469 0.122 Uiso 1 1 calc R . . C51 C 0.3252(3) 0.2646(3) 0.7827(2) 0.1074(13) Uani 1 1 d . . . H51 H 0.3133 0.2324 0.7453 0.129 Uiso 1 1 calc R . . C52 C 0.3578(3) 0.3459(3) 0.77655(17) 0.0962(11) Uani 1 1 d . . . H52 H 0.3664 0.3696 0.7352 0.115 Uiso 1 1 calc R . . C53 C 0.3778(2) 0.3926(2) 0.83190(14) 0.0716(8) Uani 1 1 d . . . H53 H 0.4013 0.4474 0.8279 0.086 Uiso 1 1 calc R . . Cl1 Cl -0.11462(9) 0.70515(6) 1.16254(5) 0.1197(4) Uani 1 1 d . . . Cl2 Cl 0.26681(9) 0.80789(6) 1.09099(5) 0.1258(4) Uani 1 1 d . . . F1 F -0.00504(14) 0.41932(13) 0.80548(8) 0.0924(6) Uani 1 1 d . . . F2 F 0.10772(16) 0.33936(14) 0.78422(8) 0.1019(6) Uani 1 1 d . . . F3 F 0.11893(16) 0.47520(14) 0.77494(8) 0.1104(7) Uani 1 1 d . . . F4 F 0.75672(11) 0.41092(12) 1.02346(10) 0.0944(6) Uani 1 1 d . . . F5 F 0.73711(12) 0.48898(13) 0.93918(11) 0.1004(6) Uani 1 1 d . . . F6 F 0.72425(11) 0.35378(12) 0.93114(10) 0.0942(6) Uani 1 1 d . . . N1 N 0.09466(13) 0.38806(12) 0.99150(9) 0.0463(5) Uani 1 1 d . . . N2 N 0.45781(13) 0.45028(12) 0.96225(9) 0.0485(5) Uani 1 1 d . . . O1 O 0.22073(18) 0.57954(16) 0.88543(12) 0.0992(7) Uani 1 1 d . . . O2 O 0.08765(19) 0.64623(15) 0.89075(14) 0.1108(9) Uani 1 1 d . . . O3 O -0.07772(13) 0.36255(13) 0.93764(10) 0.0763(6) Uani 1 1 d . . . O4 O -0.02118(12) 0.25082(11) 0.88358(9) 0.0652(5) Uani 1 1 d . . . O5 O 0.05233(15) 0.26447(11) 1.03578(9) 0.0729(6) Uani 1 1 d . . . O6 O 0.59029(14) 0.44904(14) 1.13369(10) 0.0792(6) Uani 1 1 d . . . O7 O 0.67435(16) 0.56212(16) 1.10809(12) 0.1049(8) Uani 1 1 d . . . O8 O 0.55037(16) 0.56112(13) 0.87412(11) 0.0888(7) Uani 1 1 d . . . O9 O 0.61010(16) 0.44499(13) 0.82728(10) 0.0876(6) Uani 1 1 d . . . O10 O 0.31981(12) 0.41024(13) 0.99674(9) 0.0672(5) 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 0.087(2) 0.0634(17) 0.0626(18) -0.0151(14) -0.0063(17) 0.0173(17) C2 0.097(3) 0.0595(17) 0.081(2) -0.0170(16) -0.021(2) -0.0056(18) C3 0.0621(18) 0.0590(16) 0.0716(18) -0.0068(14) -0.0110(15) -0.0091(14) C4 0.0496(16) 0.0469(13) 0.0468(14) 0.0020(11) -0.0049(12) 0.0012(11) C5 0.0502(15) 0.0528(14) 0.0687(17) -0.0116(13) 0.0011(14) -0.0024(13) C6 0.0632(18) 0.0705(18) 0.0768(19) -0.0159(16) 0.0043(16) 0.0039(16) C7 0.0399(13) 0.0510(13) 0.0506(14) 0.0064(11) -0.0035(11) -0.0069(11) C8 0.0470(14) 0.0576(15) 0.0513(14) 0.0067(12) -0.0003(12) -0.0037(12) C9 0.078(2) 0.076(2) 0.0609(17) 0.0137(16) -0.0052(16) -0.0202(18) C10 0.196(5) 0.093(3) 0.175(5) 0.064(3) -0.022(4) -0.052(3) C11 0.386(11) 0.129(4) 0.137(4) 0.048(3) -0.083(6) -0.135(6) C12 0.0437(14) 0.0699(16) 0.0491(14) 0.0035(12) 0.0034(12) 0.0001(13) C13 0.080(2) 0.087(2) 0.0513(17) 0.0034(16) 0.0028(16) -0.0084(19) C14 0.0450(14) 0.0517(13) 0.0488(14) -0.0042(11) 0.0038(12) 0.0028(11) C15 0.0526(17) 0.0550(15) 0.0522(15) -0.0065(12) 0.0028(13) -0.0021(13) C16 0.073(2) 0.091(2) 0.088(2) -0.0202(18) -0.0071(18) -0.0241(18) C17 0.0493(15) 0.0480(14) 0.0592(16) 0.0025(12) 0.0055(13) 0.0076(12) C18 0.0563(16) 0.0516(14) 0.0492(14) 0.0062(11) 0.0014(13) 0.0121(13) C19 0.0605(18) 0.0793(19) 0.0550(16) 0.0042(15) -0.0030(14) 0.0067(16) C20 0.080(2) 0.102(2) 0.065(2) -0.0058(18) -0.0185(17) 0.004(2) C21 0.119(3) 0.098(3) 0.0478(18) -0.0056(18) -0.013(2) 0.030(2) C22 0.108(3) 0.107(3) 0.055(2) 0.0145(18) 0.0135(19) 0.015(2) C23 0.077(2) 0.086(2) 0.0598(19) 0.0174(16) 0.0044(16) -0.0052(17) C24 0.083(2) 0.0597(17) 0.076(2) -0.0140(16) 0.0043(17) 0.0206(16) C25 0.125(3) 0.069(2) 0.086(2) 0.0177(18) 0.018(2) 0.037(2) C26 0.109(3) 0.0721(19) 0.0656(18) 0.0107(15) 0.0225(19) 0.0307(19) C27 0.0506(14) 0.0530(14) 0.0504(14) 0.0028(12) 0.0037(12) 0.0078(12) C28 0.092(2) 0.0716(18) 0.0577(17) 0.0025(14) 0.0041(16) 0.0289(18) C29 0.106(3) 0.092(2) 0.0593(19) -0.0108(18) 0.0045(18) 0.038(2) C30 0.0446(14) 0.0486(13) 0.0570(15) 0.0033(12) 0.0035(12) 0.0036(11) C38 0.0396(13) 0.0475(13) 0.0666(16) -0.0016(12) 0.0115(12) -0.0009(12) C39 0.0603(18) 0.0679(18) 0.0729(19) 0.0005(16) 0.0149(15) -0.0034(15) C40 0.167(4) 0.145(4) 0.095(3) 0.013(3) 0.075(3) -0.014(3) C41 0.0384(13) 0.0479(13) 0.0749(16) -0.0041(12) 0.0013(12) 0.0013(11) C42 0.0443(16) 0.0671(19) 0.103(2) -0.0174(19) 0.0029(17) 0.0019(15) C43 0.0458(14) 0.0492(14) 0.0752(18) -0.0071(13) 0.0006(13) 0.0000(12) C44 0.0519(17) 0.0632(18) 0.090(2) -0.0192(17) -0.0024(16) 0.0046(15) C45 0.093(3) 0.118(3) 0.081(2) -0.023(2) -0.029(2) 0.020(2) C46 0.190(5) 0.115(3) 0.089(3) 0.010(2) -0.039(3) -0.005(3) C47 0.0418(14) 0.0545(14) 0.0605(15) 0.0067(12) 0.0033(13) 0.0044(12) C48 0.0400(14) 0.0616(15) 0.0611(17) -0.0007(13) -0.0005(12) 0.0007(12) C49 0.065(2) 0.0749(19) 0.087(2) -0.0026(18) -0.0131(17) -0.0114(16) C50 0.092(3) 0.085(2) 0.129(4) -0.015(3) -0.028(3) -0.014(2) C51 0.099(3) 0.118(3) 0.106(3) -0.043(3) -0.030(3) 0.009(3) C52 0.091(3) 0.133(3) 0.064(2) -0.012(2) -0.0091(19) 0.009(3) C53 0.0639(19) 0.084(2) 0.0665(19) 0.0044(16) -0.0036(16) -0.0045(16) Cl1 0.1478(10) 0.1024(7) 0.1088(7) -0.0479(6) 0.0114(7) 0.0363(7) Cl2 0.1634(11) 0.0880(6) 0.1260(8) -0.0206(6) 0.0051(8) 0.0642(7) F1 0.0856(14) 0.1204(15) 0.0713(11) 0.0073(10) -0.0250(10) -0.0057(12) F2 0.1268(17) 0.1163(15) 0.0625(11) -0.0225(10) 0.0145(11) 0.0007(13) F3 0.1426(19) 0.1311(16) 0.0575(10) 0.0233(10) 0.0054(12) -0.0436(15) F4 0.0485(10) 0.1102(14) 0.1243(15) -0.0212(12) -0.0142(10) 0.0123(10) F5 0.0596(11) 0.0902(13) 0.1516(18) -0.0015(12) 0.0254(12) -0.0224(10) F6 0.0511(10) 0.0956(12) 0.1360(16) -0.0449(12) 0.0141(10) 0.0057(9) N1 0.0441(11) 0.0470(11) 0.0477(11) 0.0006(9) 0.0031(10) 0.0037(9) N2 0.0411(11) 0.0517(11) 0.0528(12) -0.0018(9) 0.0071(10) 0.0031(10) O1 0.0818(16) 0.1085(18) 0.1071(17) 0.0222(14) 0.0174(14) -0.0347(15) O2 0.113(2) 0.0671(14) 0.152(2) 0.0421(15) -0.0141(18) -0.0157(14) O3 0.0444(11) 0.0866(13) 0.0979(15) -0.0349(12) 0.0051(11) 0.0022(10) O4 0.0618(13) 0.0651(11) 0.0687(12) -0.0187(9) 0.0038(10) -0.0067(9) O5 0.1015(16) 0.0480(10) 0.0694(12) 0.0016(9) 0.0037(11) -0.0063(10) O6 0.0786(14) 0.0852(14) 0.0738(13) -0.0058(11) -0.0242(12) -0.0008(12) O7 0.0869(17) 0.1030(17) 0.125(2) -0.0376(16) -0.0132(14) -0.0260(15) O8 0.1110(17) 0.0623(13) 0.0932(15) 0.0144(12) 0.0332(13) 0.0045(13) O9 0.0943(16) 0.0865(14) 0.0821(14) -0.0056(11) 0.0436(13) -0.0060(13) O10 0.0483(10) 0.0849(13) 0.0685(12) -0.0037(10) 0.0166(9) -0.0019(10) _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 C2 1.354(4) . ? C1 C6 1.366(4) . ? C1 Cl1 1.734(3) . ? C2 C3 1.386(4) . ? C2 H2 0.9300 . ? C3 C4 1.378(3) . ? C3 H3 0.9300 . ? C4 C5 1.369(3) . ? C4 C7 1.505(3) . ? C5 C6 1.380(3) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 N1 1.474(3) . ? C7 C8 1.546(3) . ? C7 H7 0.9800 . ? C8 C9 1.512(4) . ? C8 C12 1.527(3) . ? C8 H8 0.9800 . ? C9 O1 1.192(4) . ? C9 O2 1.318(4) . ? C10 C11 1.355(6) . ? C10 O2 1.458(4) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 C13 1.497(4) . ? C12 C14 1.528(3) . ? C12 H12 0.9800 . ? C13 F2 1.325(4) . ? C13 F3 1.330(3) . ? C13 F1 1.338(3) . ? C14 N1 1.455(3) . ? C14 C15 1.523(3) . ? C14 H14 0.9800 . ? C15 O3 1.183(3) . ? C15 O4 1.331(3) . ? C16 O4 1.443(3) . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C17 O5 1.230(3) . ? C17 N1 1.358(3) . ? C17 C18 1.477(4) . ? C18 C19 1.373(4) . ? C18 C23 1.376(4) . ? C19 C20 1.378(4) . ? C19 H19 0.9300 . ? C20 C21 1.369(5) . ? C20 H20 0.9300 . ? C21 C22 1.366(5) . ? C21 H21 0.9300 . ? C22 C23 1.377(4) . ? C22 H22 0.9300 . ? C23 H23 0.9300 . ? C24 C25 1.344(4) . ? C24 C29 1.348(4) . ? C24 Cl2 1.746(3) . ? C25 C26 1.391(4) . ? C25 H25 0.9300 . ? C26 C27 1.368(4) . ? C26 H26 0.9300 . ? C27 C28 1.372(3) . ? C27 C30 1.505(3) . ? C28 C29 1.373(4) . ? C28 H28 0.9300 . ? C29 H29 0.9300 . ? C30 N2 1.471(3) . ? C30 C43 1.538(3) . ? C30 H30 0.9800 . ? C38 N2 1.466(3) . ? C38 C39 1.520(4) . ? C38 C41 1.531(3) . ? C38 H38 0.9800 . ? C39 O8 1.193(3) . ? C39 O9 1.332(3) . ? C40 O9 1.454(4) . ? C40 H40A 0.9600 . ? C40 H40B 0.9600 . ? C40 H40C 0.9600 . ? C41 C42 1.496(4) . ? C41 C43 1.526(3) . ? C41 H41 0.9800 . ? C42 F5 1.316(3) . ? C42 F6 1.329(3) . ? C42 F4 1.342(3) . ? C43 C44 1.500(4) . ? C43 H43 0.9800 . ? C44 O7 1.198(3) . ? C44 O6 1.327(4) . ? C45 C46 1.454(5) . ? C45 O6 1.456(4) . ? C45 H45A 0.9700 . ? C45 H45B 0.9700 . ? C46 H46A 0.9600 . ? C46 H46B 0.9600 . ? C46 H46C 0.9600 . ? C47 O10 1.219(3) . ? C47 N2 1.365(3) . ? C47 C48 1.494(4) . ? C48 C53 1.367(4) . ? C48 C49 1.378(4) . ? C49 C50 1.375(5) . ? C49 H49 0.9300 . ? C50 C51 1.362(5) . ? C50 H50 0.9300 . ? C51 C52 1.367(5) . ? C51 H51 0.9300 . ? C52 C53 1.377(4) . ? C52 H52 0.9300 . ? C53 H53 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C6 121.2(3) . . ? C2 C1 Cl1 119.8(2) . . ? C6 C1 Cl1 119.0(3) . . ? C1 C2 C3 119.5(3) . . ? C1 C2 H2 120.2 . . ? C3 C2 H2 120.2 . . ? C4 C3 C2 120.4(3) . . ? C4 C3 H3 119.8 . . ? C2 C3 H3 119.8 . . ? C5 C4 C3 118.7(2) . . ? C5 C4 C7 122.3(2) . . ? C3 C4 C7 118.8(2) . . ? C4 C5 C6 121.2(2) . . ? C4 C5 H5 119.4 . . ? C6 C5 H5 119.4 . . ? C1 C6 C5 118.9(3) . . ? C1 C6 H6 120.5 . . ? C5 C6 H6 120.5 . . ? N1 C7 C4 115.68(19) . . ? N1 C7 C8 101.79(18) . . ? C4 C7 C8 111.88(19) . . ? N1 C7 H7 109.1 . . ? C4 C7 H7 109.1 . . ? C8 C7 H7 109.1 . . ? C9 C8 C12 113.7(2) . . ? C9 C8 C7 110.0(2) . . ? C12 C8 C7 102.86(19) . . ? C9 C8 H8 110.0 . . ? C12 C8 H8 110.0 . . ? C7 C8 H8 110.0 . . ? O1 C9 O2 125.4(3) . . ? O1 C9 C8 124.0(3) . . ? O2 C9 C8 110.5(3) . . ? C11 C10 O2 110.2(4) . . ? C11 C10 H10A 109.6 . . ? O2 C10 H10A 109.6 . . ? C11 C10 H10B 109.6 . . ? O2 C10 H10B 109.6 . . ? H10A C10 H10B 108.1 . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C13 C12 C8 114.9(2) . . ? C13 C12 C14 115.7(2) . . ? C8 C12 C14 103.48(18) . . ? C13 C12 H12 107.4 . . ? C8 C12 H12 107.4 . . ? C14 C12 H12 107.4 . . ? F2 C13 F3 107.6(2) . . ? F2 C13 F1 106.3(3) . . ? F3 C13 F1 105.7(3) . . ? F2 C13 C12 112.3(3) . . ? F3 C13 C12 111.5(3) . . ? F1 C13 C12 113.1(2) . . ? N1 C14 C15 109.7(2) . . ? N1 C14 C12 102.14(18) . . ? C15 C14 C12 115.3(2) . . ? N1 C14 H14 109.8 . . ? C15 C14 H14 109.8 . . ? C12 C14 H14 109.8 . . ? O3 C15 O4 125.0(2) . . ? O3 C15 C14 124.2(2) . . ? O4 C15 C14 110.8(2) . . ? O4 C16 H16A 109.5 . . ? O4 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? O4 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? O5 C17 N1 118.5(2) . . ? O5 C17 C18 120.5(2) . . ? N1 C17 C18 121.0(2) . . ? C19 C18 C23 119.2(3) . . ? C19 C18 C17 122.7(2) . . ? C23 C18 C17 117.9(3) . . ? C18 C19 C20 120.2(3) . . ? C18 C19 H19 119.9 . . ? C20 C19 H19 119.9 . . ? C21 C20 C19 120.0(3) . . ? C21 C20 H20 120.0 . . ? C19 C20 H20 120.0 . . ? C22 C21 C20 120.2(3) . . ? C22 C21 H21 119.9 . . ? C20 C21 H21 119.9 . . ? C21 C22 C23 119.8(3) . . ? C21 C22 H22 120.1 . . ? C23 C22 H22 120.1 . . ? C18 C23 C22 120.5(3) . . ? C18 C23 H23 119.8 . . ? C22 C23 H23 119.8 . . ? C25 C24 C29 121.2(3) . . ? C25 C24 Cl2 119.4(3) . . ? C29 C24 Cl2 119.4(2) . . ? C24 C25 C26 119.5(3) . . ? C24 C25 H25 120.2 . . ? C26 C25 H25 120.2 . . ? C27 C26 C25 120.7(3) . . ? C27 C26 H26 119.6 . . ? C25 C26 H26 119.6 . . ? C26 C27 C28 117.5(2) . . ? C26 C27 C30 123.1(2) . . ? C28 C27 C30 119.3(2) . . ? C27 C28 C29 121.9(3) . . ? C27 C28 H28 119.1 . . ? C29 C28 H28 119.1 . . ? C24 C29 C28 119.1(3) . . ? C24 C29 H29 120.5 . . ? C28 C29 H29 120.5 . . ? N2 C30 C27 115.28(19) . . ? N2 C30 C43 102.79(19) . . ? C27 C30 C43 114.5(2) . . ? N2 C30 H30 107.9 . . ? C27 C30 H30 107.9 . . ? C43 C30 H30 107.9 . . ? N2 C38 C39 111.3(2) . . ? N2 C38 C41 101.08(18) . . ? C39 C38 C41 113.9(2) . . ? N2 C38 H38 110.1 . . ? C39 C38 H38 110.1 . . ? C41 C38 H38 110.1 . . ? O8 C39 O9 124.5(3) . . ? O8 C39 C38 125.8(3) . . ? O9 C39 C38 109.7(2) . . ? O9 C40 H40A 109.5 . . ? O9 C40 H40B 109.5 . . ? H40A C40 H40B 109.5 . . ? O9 C40 H40C 109.5 . . ? H40A C40 H40C 109.5 . . ? H40B C40 H40C 109.5 . . ? C42 C41 C43 116.0(2) . . ? C42 C41 C38 116.6(2) . . ? C43 C41 C38 102.6(2) . . ? C42 C41 H41 107.0 . . ? C43 C41 H41 107.0 . . ? C38 C41 H41 107.0 . . ? F5 C42 F6 107.4(3) . . ? F5 C42 F4 106.4(2) . . ? F6 C42 F4 106.4(2) . . ? F5 C42 C41 114.4(3) . . ? F6 C42 C41 111.2(2) . . ? F4 C42 C41 110.5(3) . . ? C44 C43 C41 115.0(2) . . ? C44 C43 C30 114.5(2) . . ? C41 C43 C30 101.05(19) . . ? C44 C43 H43 108.6 . . ? C41 C43 H43 108.6 . . ? C30 C43 H43 108.6 . . ? O7 C44 O6 123.6(3) . . ? O7 C44 C43 124.1(3) . . ? O6 C44 C43 112.3(2) . . ? C46 C45 O6 108.1(3) . . ? C46 C45 H45A 110.1 . . ? O6 C45 H45A 110.1 . . ? C46 C45 H45B 110.1 . . ? O6 C45 H45B 110.1 . . ? H45A C45 H45B 108.4 . . ? C45 C46 H46A 109.5 . . ? C45 C46 H46B 109.5 . . ? H46A C46 H46B 109.5 . . ? C45 C46 H46C 109.5 . . ? H46A C46 H46C 109.5 . . ? H46B C46 H46C 109.5 . . ? O10 C47 N2 120.8(2) . . ? O10 C47 C48 120.7(2) . . ? N2 C47 C48 118.5(2) . . ? C53 C48 C49 120.1(3) . . ? C53 C48 C47 122.7(2) . . ? C49 C48 C47 117.1(3) . . ? C50 C49 C48 119.4(3) . . ? C50 C49 H49 120.3 . . ? C48 C49 H49 120.3 . . ? C51 C50 C49 120.3(4) . . ? C51 C50 H50 119.8 . . ? C49 C50 H50 119.8 . . ? C50 C51 C52 120.4(4) . . ? C50 C51 H51 119.8 . . ? C52 C51 H51 119.8 . . ? C51 C52 C53 119.7(4) . . ? C51 C52 H52 120.2 . . ? C53 C52 H52 120.2 . . ? C48 C53 C52 120.1(3) . . ? C48 C53 H53 120.0 . . ? C52 C53 H53 120.0 . . ? C17 N1 C14 116.87(19) . . ? C17 N1 C7 129.01(19) . . ? C14 N1 C7 113.81(18) . . ? C47 N2 C38 122.68(19) . . ? C47 N2 C30 117.33(19) . . ? C38 N2 C30 112.35(19) . . ? C9 O2 C10 118.1(3) . . ? C15 O4 C16 115.0(2) . . ? C44 O6 C45 115.6(3) . . ? C39 O9 C40 115.8(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 -2.1(5) . . . . ? Cl1 C1 C2 C3 179.2(2) . . . . ? C1 C2 C3 C4 1.5(4) . . . . ? C2 C3 C4 C5 0.3(4) . . . . ? C2 C3 C4 C7 174.9(2) . . . . ? C3 C4 C5 C6 -1.6(4) . . . . ? C7 C4 C5 C6 -176.0(2) . . . . ? C2 C1 C6 C5 0.8(5) . . . . ? Cl1 C1 C6 C5 179.5(2) . . . . ? C4 C5 C6 C1 1.1(4) . . . . ? C5 C4 C7 N1 -41.6(3) . . . . ? C3 C4 C7 N1 144.0(2) . . . . ? C5 C4 C7 C8 74.3(3) . . . . ? C3 C4 C7 C8 -100.1(3) . . . . ? N1 C7 C8 C9 -152.2(2) . . . . ? C4 C7 C8 C9 83.7(3) . . . . ? N1 C7 C8 C12 -30.7(2) . . . . ? C4 C7 C8 C12 -154.85(19) . . . . ? C12 C8 C9 O1 -42.6(4) . . . . ? C7 C8 C9 O1 72.2(4) . . . . ? C12 C8 C9 O2 140.3(3) . . . . ? C7 C8 C9 O2 -104.9(3) . . . . ? C9 C8 C12 C13 -73.7(3) . . . . ? C7 C8 C12 C13 167.4(2) . . . . ? C9 C8 C12 C14 159.2(2) . . . . ? C7 C8 C12 C14 40.3(2) . . . . ? C8 C12 C13 F2 -177.8(2) . . . . ? C14 C12 C13 F2 -57.2(3) . . . . ? C8 C12 C13 F3 61.3(3) . . . . ? C14 C12 C13 F3 -178.1(2) . . . . ? C8 C12 C13 F1 -57.5(3) . . . . ? C14 C12 C13 F1 63.0(3) . . . . ? C13 C12 C14 N1 -159.9(2) . . . . ? C8 C12 C14 N1 -33.3(2) . . . . ? C13 C12 C14 C15 -41.1(3) . . . . ? C8 C12 C14 C15 85.5(2) . . . . ? N1 C14 C15 O3 37.3(3) . . . . ? C12 C14 C15 O3 -77.2(3) . . . . ? N1 C14 C15 O4 -145.0(2) . . . . ? C12 C14 C15 O4 100.5(2) . . . . ? O5 C17 C18 C19 135.0(3) . . . . ? N1 C17 C18 C19 -43.9(4) . . . . ? O5 C17 C18 C23 -39.1(4) . . . . ? N1 C17 C18 C23 142.1(2) . . . . ? C23 C18 C19 C20 0.9(4) . . . . ? C17 C18 C19 C20 -173.1(3) . . . . ? C18 C19 C20 C21 -1.7(5) . . . . ? C19 C20 C21 C22 0.1(5) . . . . ? C20 C21 C22 C23 2.2(5) . . . . ? C19 C18 C23 C22 1.5(4) . . . . ? C17 C18 C23 C22 175.7(3) . . . . ? C21 C22 C23 C18 -3.1(5) . . . . ? C29 C24 C25 C26 -1.2(6) . . . . ? Cl2 C24 C25 C26 -178.6(3) . . . . ? C24 C25 C26 C27 0.3(6) . . . . ? C25 C26 C27 C28 1.0(5) . . . . ? C25 C26 C27 C30 -178.4(3) . . . . ? C26 C27 C28 C29 -1.5(5) . . . . ? C30 C27 C28 C29 178.0(3) . . . . ? C25 C24 C29 C28 0.8(6) . . . . ? Cl2 C24 C29 C28 178.1(3) . . . . ? C27 C28 C29 C24 0.6(5) . . . . ? C26 C27 C30 N2 -38.9(4) . . . . ? C28 C27 C30 N2 141.7(3) . . . . ? C26 C27 C30 C43 80.1(3) . . . . ? C28 C27 C30 C43 -99.3(3) . . . . ? N2 C38 C39 O8 31.6(4) . . . . ? C41 C38 C39 O8 -81.8(4) . . . . ? N2 C38 C39 O9 -149.9(2) . . . . ? C41 C38 C39 O9 96.7(3) . . . . ? N2 C38 C41 C42 -166.2(2) . . . . ? C39 C38 C41 C42 -46.8(3) . . . . ? N2 C38 C41 C43 -38.3(2) . . . . ? C39 C38 C41 C43 81.1(3) . . . . ? C43 C41 C42 F5 -54.0(4) . . . . ? C38 C41 C42 F5 67.0(3) . . . . ? C43 C41 C42 F6 -175.9(3) . . . . ? C38 C41 C42 F6 -54.9(3) . . . . ? C43 C41 C42 F4 66.0(3) . . . . ? C38 C41 C42 F4 -172.9(2) . . . . ? C42 C41 C43 C44 -63.1(3) . . . . ? C38 C41 C43 C44 168.6(2) . . . . ? C42 C41 C43 C30 173.1(2) . . . . ? C38 C41 C43 C30 44.8(2) . . . . ? N2 C30 C43 C44 -157.5(2) . . . . ? C27 C30 C43 C44 76.7(3) . . . . ? N2 C30 C43 C41 -33.3(2) . . . . ? C27 C30 C43 C41 -159.1(2) . . . . ? C41 C43 C44 O7 110.0(3) . . . . ? C30 C43 C44 O7 -133.6(3) . . . . ? C41 C43 C44 O6 -69.4(3) . . . . ? C30 C43 C44 O6 47.1(3) . . . . ? O10 C47 C48 C53 129.8(3) . . . . ? N2 C47 C48 C53 -49.4(4) . . . . ? O10 C47 C48 C49 -47.0(4) . . . . ? N2 C47 C48 C49 133.8(3) . . . . ? C53 C48 C49 C50 -0.3(5) . . . . ? C47 C48 C49 C50 176.6(3) . . . . ? C48 C49 C50 C51 0.8(5) . . . . ? C49 C50 C51 C52 -1.6(6) . . . . ? C50 C51 C52 C53 1.9(6) . . . . ? C49 C48 C53 C52 0.6(5) . . . . ? C47 C48 C53 C52 -176.1(3) . . . . ? C51 C52 C53 C48 -1.5(5) . . . . ? O5 C17 N1 C14 -8.0(3) . . . . ? C18 C17 N1 C14 170.9(2) . . . . ? O5 C17 N1 C7 165.2(2) . . . . ? C18 C17 N1 C7 -15.9(4) . . . . ? C15 C14 N1 C17 65.7(3) . . . . ? C12 C14 N1 C17 -171.5(2) . . . . ? C15 C14 N1 C7 -108.5(2) . . . . ? C12 C14 N1 C7 14.2(3) . . . . ? C4 C7 N1 C17 -41.4(3) . . . . ? C8 C7 N1 C17 -163.0(2) . . . . ? C4 C7 N1 C14 131.9(2) . . . . ? C8 C7 N1 C14 10.4(3) . . . . ? O10 C47 N2 C38 154.9(2) . . . . ? C48 C47 N2 C38 -25.9(3) . . . . ? O10 C47 N2 C30 7.8(3) . . . . ? C48 C47 N2 C30 -173.1(2) . . . . ? C39 C38 N2 C47 107.8(3) . . . . ? C41 C38 N2 C47 -131.0(2) . . . . ? C39 C38 N2 C30 -103.6(2) . . . . ? C41 C38 N2 C30 17.6(2) . . . . ? C27 C30 N2 C47 -74.3(3) . . . . ? C43 C30 N2 C47 160.3(2) . . . . ? C27 C30 N2 C38 135.2(2) . . . . ? C43 C30 N2 C38 9.9(2) . . . . ? O1 C9 O2 C10 -5.0(5) . . . . ? C8 C9 O2 C10 172.0(3) . . . . ? C11 C10 O2 C9 105.5(6) . . . . ? O3 C15 O4 C16 -0.4(4) . . . . ? C14 C15 O4 C16 -178.1(2) . . . . ? O7 C44 O6 C45 -0.1(4) . . . . ? C43 C44 O6 C45 179.3(2) . . . . ? C46 C45 O6 C44 176.6(3) . . . . ? O8 C39 O9 C40 2.8(5) . . . . ? C38 C39 O9 C40 -175.8(3) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.269 _refine_diff_density_min -0.275 _refine_diff_density_rms 0.028