# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Sorensen, Erik' _publ_contact_author_email ejs@princeton.edu _publ_section_title ; A Concise Synthesis of the Molecular Framework of Pleuromutilin ; loop_ _publ_author_name J.Liu S.Lotesta E.Sorensen # Attachment '- cyanoketone 13 X-ray.cif' data_lotest3 _database_code_depnum_ccdc_archive 'CCDC 798052' #TrackingRef '- cyanoketone 13 X-ray.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H15 N O' _chemical_formula_weight 189.25 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 7.2455(5) _cell_length_b 6.4925(4) _cell_length_c 11.1739(7) _cell_angle_alpha 90.00 _cell_angle_beta 102.217(1) _cell_angle_gamma 90.00 _cell_volume 513.73(6) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 4982 _cell_measurement_theta_min 3.08 _cell_measurement_theta_max 30.53 _exptl_crystal_description lathe _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.223 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 204 _exptl_absorpt_coefficient_mu 0.078 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9846 _exptl_absorpt_correction_T_max 0.9892 _exptl_absorpt_process_details 'Bruker SAINT (SADABS)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type '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 6303 _diffrn_reflns_av_R_equivalents 0.0118 _diffrn_reflns_av_sigmaI/netI 0.0183 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.86 _diffrn_reflns_theta_max 30.53 _reflns_number_total 3056 _reflns_number_gt 2956 _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^)+(0.0600P)^2^+0.0880P] 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 0.2(11) _refine_ls_number_reflns 3056 _refine_ls_number_parameters 127 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0402 _refine_ls_R_factor_gt 0.0389 _refine_ls_wR_factor_ref 0.0968 _refine_ls_wR_factor_gt 0.0954 _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_restrained_S_all 1.042 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O -0.58723(12) 0.14805(15) 0.02814(8) 0.02470(19) Uani 1 1 d . . . N1 N -0.33381(16) 0.4485(2) 0.47457(11) 0.0303(3) Uani 1 1 d . . . C1 C -0.32470(14) 0.28349(16) 0.17940(10) 0.01575(19) Uani 1 1 d . . . H1 H -0.3481 0.4354 0.1744 0.019 Uiso 1 1 calc R . . C2 C -0.40841(15) 0.20107(18) 0.28521(10) 0.0189(2) Uani 1 1 d . . . H2 H -0.5488 0.1953 0.2567 0.023 Uiso 1 1 calc R . . C3 C -0.33799(17) -0.01778(18) 0.32240(11) 0.0215(2) Uani 1 1 d . . . H3A H -0.3833 -0.0603 0.3963 0.026 Uiso 1 1 calc R . . H3B H -0.3902 -0.1150 0.2556 0.026 Uiso 1 1 calc R . . C4 C -0.12257(16) -0.02671(18) 0.34884(10) 0.0205(2) Uani 1 1 d . . . H4A H -0.0798 -0.1678 0.3745 0.025 Uiso 1 1 calc R . . H4B H -0.0701 0.0686 0.4167 0.025 Uiso 1 1 calc R . . C5 C -0.04994(16) 0.03326(17) 0.23462(10) 0.0181(2) Uani 1 1 d . . . H5A H -0.0970 -0.0680 0.1690 0.022 Uiso 1 1 calc R . . H5B H 0.0897 0.0260 0.2538 0.022 Uiso 1 1 calc R . . C6 C -0.11069(14) 0.25014(16) 0.18700(9) 0.01486(19) Uani 1 1 d . . . C7 C -0.09922(15) 0.27082(17) 0.05049(10) 0.0177(2) Uani 1 1 d . . . H7A H -0.0953 0.4177 0.0273 0.021 Uiso 1 1 calc R . . H7B H 0.0155 0.2017 0.0353 0.021 Uiso 1 1 calc R . . C8 C -0.27691(16) 0.16724(18) -0.02303(10) 0.0199(2) Uani 1 1 d . . . H8A H -0.3203 0.2362 -0.1031 0.024 Uiso 1 1 calc R . . H8B H -0.2534 0.0200 -0.0372 0.024 Uiso 1 1 calc R . . C9 C -0.42106(15) 0.19137(17) 0.05661(10) 0.0180(2) Uani 1 1 d . . . C10 C 0.00356(15) 0.42240(18) 0.25763(10) 0.0187(2) Uani 1 1 d . . . H10 H -0.0373 0.5582 0.2338 0.022 Uiso 1 1 calc R . . C11 C 0.15390(16) 0.4080(2) 0.34881(11) 0.0227(2) Uani 1 1 d . . . H11A H 0.2018 0.2765 0.3769 0.027 Uiso 1 1 calc R . . H11B H 0.2135 0.5293 0.3859 0.027 Uiso 1 1 calc R . . C12 C -0.36515(16) 0.3407(2) 0.39169(11) 0.0219(2) 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 O1 0.0204(4) 0.0259(4) 0.0268(4) -0.0059(4) 0.0026(3) -0.0019(3) N1 0.0243(5) 0.0391(7) 0.0282(5) -0.0107(5) 0.0074(4) -0.0019(5) C1 0.0148(4) 0.0152(4) 0.0172(4) -0.0021(4) 0.0034(3) 0.0006(4) C2 0.0162(4) 0.0226(5) 0.0188(5) -0.0037(4) 0.0054(4) -0.0015(4) C3 0.0241(5) 0.0207(5) 0.0208(5) 0.0003(4) 0.0071(4) -0.0055(4) C4 0.0249(5) 0.0176(5) 0.0193(5) 0.0032(4) 0.0057(4) 0.0019(4) C5 0.0209(5) 0.0149(4) 0.0193(5) 0.0006(4) 0.0062(4) 0.0031(4) C6 0.0154(4) 0.0134(4) 0.0160(4) -0.0004(3) 0.0039(3) 0.0004(3) C7 0.0200(4) 0.0166(4) 0.0176(4) -0.0003(4) 0.0062(4) -0.0006(4) C8 0.0227(5) 0.0210(5) 0.0162(4) -0.0020(4) 0.0044(4) 0.0006(4) C9 0.0203(5) 0.0148(5) 0.0182(4) -0.0008(4) 0.0026(4) 0.0012(4) C10 0.0185(4) 0.0170(5) 0.0213(5) -0.0029(4) 0.0059(4) -0.0012(4) C11 0.0190(5) 0.0277(6) 0.0220(5) -0.0034(4) 0.0055(4) -0.0022(4) C12 0.0163(5) 0.0277(6) 0.0229(5) -0.0026(5) 0.0066(4) 0.0010(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C9 1.2115(13) . ? N1 C12 1.1448(16) . ? C1 C9 1.5240(15) . ? C1 C2 1.5348(15) . ? C1 C6 1.5501(14) . ? C1 H1 1.0000 . ? C2 C12 1.4757(16) . ? C2 C3 1.5370(17) . ? C2 H2 1.0000 . ? C3 C4 1.5269(16) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.5302(15) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.5364(15) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C10 1.5108(15) . ? C6 C7 1.5509(15) . ? C7 C8 1.5287(16) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.5167(15) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C10 C11 1.3280(16) . ? C10 H10 0.9500 . ? C11 H11A 0.9500 . ? C11 H11B 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 C9 C1 C2 112.10(9) . . ? C9 C1 C6 104.88(8) . . ? C2 C1 C6 117.58(8) . . ? C9 C1 H1 107.3 . . ? C2 C1 H1 107.3 . . ? C6 C1 H1 107.3 . . ? C12 C2 C1 110.84(10) . . ? C12 C2 C3 110.37(9) . . ? C1 C2 C3 111.59(9) . . ? C12 C2 H2 108.0 . . ? C1 C2 H2 108.0 . . ? C3 C2 H2 108.0 . . ? C4 C3 C2 110.77(9) . . ? C4 C3 H3A 109.5 . . ? C2 C3 H3A 109.5 . . ? C4 C3 H3B 109.5 . . ? C2 C3 H3B 109.5 . . ? H3A C3 H3B 108.1 . . ? C3 C4 C5 110.29(9) . . ? C3 C4 H4A 109.6 . . ? C5 C4 H4A 109.6 . . ? C3 C4 H4B 109.6 . . ? C5 C4 H4B 109.6 . . ? H4A C4 H4B 108.1 . . ? C4 C5 C6 113.47(9) . . ? C4 C5 H5A 108.9 . . ? C6 C5 H5A 108.9 . . ? C4 C5 H5B 108.9 . . ? C6 C5 H5B 108.9 . . ? H5A C5 H5B 107.7 . . ? C10 C6 C5 114.36(9) . . ? C10 C6 C1 110.88(9) . . ? C5 C6 C1 110.91(8) . . ? C10 C6 C7 108.19(9) . . ? C5 C6 C7 110.43(9) . . ? C1 C6 C7 101.26(8) . . ? C8 C7 C6 106.03(8) . . ? C8 C7 H7A 110.5 . . ? C6 C7 H7A 110.5 . . ? C8 C7 H7B 110.5 . . ? C6 C7 H7B 110.5 . . ? H7A C7 H7B 108.7 . . ? C9 C8 C7 104.21(9) . . ? C9 C8 H8A 110.9 . . ? C7 C8 H8A 110.9 . . ? C9 C8 H8B 110.9 . . ? C7 C8 H8B 110.9 . . ? H8A C8 H8B 108.9 . . ? O1 C9 C8 126.26(10) . . ? O1 C9 C1 124.61(10) . . ? C8 C9 C1 109.12(9) . . ? C11 C10 C6 128.21(11) . . ? C11 C10 H10 115.9 . . ? C6 C10 H10 115.9 . . ? C10 C11 H11A 120.0 . . ? C10 C11 H11B 120.0 . . ? H11A C11 H11B 120.0 . . ? N1 C12 C2 179.14(12) . . ? 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 C9 C1 C2 C12 -159.64(9) . . . . ? C6 C1 C2 C12 78.70(12) . . . . ? C9 C1 C2 C3 76.91(11) . . . . ? C6 C1 C2 C3 -44.75(12) . . . . ? C12 C2 C3 C4 -70.67(12) . . . . ? C1 C2 C3 C4 53.05(12) . . . . ? C2 C3 C4 C5 -60.59(12) . . . . ? C3 C4 C5 C6 58.77(12) . . . . ? C4 C5 C6 C10 78.65(12) . . . . ? C4 C5 C6 C1 -47.63(12) . . . . ? C4 C5 C6 C7 -159.05(9) . . . . ? C9 C1 C6 C10 147.95(9) . . . . ? C2 C1 C6 C10 -86.74(11) . . . . ? C9 C1 C6 C5 -83.87(10) . . . . ? C2 C1 C6 C5 41.44(12) . . . . ? C9 C1 C6 C7 33.32(10) . . . . ? C2 C1 C6 C7 158.64(9) . . . . ? C10 C6 C7 C8 -154.80(9) . . . . ? C5 C6 C7 C8 79.35(10) . . . . ? C1 C6 C7 C8 -38.20(11) . . . . ? C6 C7 C8 C9 27.99(11) . . . . ? C7 C8 C9 O1 172.60(11) . . . . ? C7 C8 C9 C1 -6.42(12) . . . . ? C2 C1 C9 O1 34.92(15) . . . . ? C6 C1 C9 O1 163.60(11) . . . . ? C2 C1 C9 C8 -146.04(9) . . . . ? C6 C1 C9 C8 -17.36(11) . . . . ? C5 C6 C10 C11 4.53(16) . . . . ? C1 C6 C10 C11 130.83(12) . . . . ? C7 C6 C10 C11 -118.97(12) . . . . ? C1 C2 C12 N1 141(10) . . . . ? C3 C2 C12 N1 -94(10) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 30.53 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.349 _refine_diff_density_min -0.176 _refine_diff_density_rms 0.052 # Attachment '- trityl side chain-epoxide 31 X-ray.cif' data_lotest4 _database_code_depnum_ccdc_archive 'CCDC 798053' #TrackingRef '- trityl side chain-epoxide 31 X-ray.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '(C38 H42 O6), 0.5(C H2 CL2)' _chemical_formula_sum 'C38.50 H43 Cl O6' _chemical_formula_weight 637.18 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' Cl Cl 0.1484 0.1585 '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)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.5755(10) _cell_length_b 11.3095(13) _cell_length_c 33.730(4) _cell_angle_alpha 90.00 _cell_angle_beta 94.856(3) _cell_angle_gamma 90.00 _cell_volume 3259.6(7) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5663 _cell_measurement_theta_min 2.41 _cell_measurement_theta_max 31.78 _exptl_crystal_description lathe _exptl_crystal_colour colourless _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.298 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1356 _exptl_absorpt_coefficient_mu 0.165 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.958 _exptl_absorpt_correction_T_max 0.99 _exptl_absorpt_process_details 'Bruker SAINT (SADABS)' _exptl_special_details ; Crystal was twinned. Only one component was used. ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11172 _diffrn_reflns_av_R_equivalents 0.0485 _diffrn_reflns_av_sigmaI/netI 0.0637 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -40 _diffrn_reflns_limit_l_max 40 _diffrn_reflns_theta_min 1.90 _diffrn_reflns_theta_max 25.35 _reflns_number_total 5903 _reflns_number_gt 4485 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _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^)+(0.0600P)^2^+6.9000P] 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 5903 _refine_ls_number_parameters 425 _refine_ls_number_restraints 30 _refine_ls_R_factor_all 0.0987 _refine_ls_R_factor_gt 0.0727 _refine_ls_wR_factor_ref 0.1709 _refine_ls_wR_factor_gt 0.1597 _refine_ls_goodness_of_fit_ref 1.022 _refine_ls_restrained_S_all 1.021 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.7253(3) 1.0156(2) 0.00898(6) 0.0245(5) Uani 1 1 d . . . O2 O 0.4707(3) 0.7235(2) 0.15351(7) 0.0234(5) Uani 1 1 d . . . O3 O 0.5250(2) 0.70319(19) 0.08954(6) 0.0186(5) Uani 1 1 d . . . O4 O 0.3079(2) 0.52246(18) 0.14976(6) 0.0181(5) Uani 1 1 d . . . O5 O 0.9042(3) 0.9748(2) 0.18165(6) 0.0228(5) Uani 1 1 d . . . O6 O 0.9997(3) 0.78739(19) 0.18271(6) 0.0221(5) Uani 1 1 d . . . C1 C 0.8975(4) 0.8800(3) 0.11830(9) 0.0150(6) Uani 1 1 d . . . H1 H 0.8333 0.9534 0.1140 0.018 Uiso 1 1 calc R . . C2 C 1.0218(4) 0.8840(3) 0.08779(9) 0.0184(7) Uani 1 1 d . . . C3 C 0.9638(4) 0.9281(3) 0.04602(10) 0.0231(7) Uani 1 1 d . . . H3A H 1.0530 0.9645 0.0337 0.028 Uiso 1 1 calc R . . H3B H 0.9290 0.8590 0.0296 0.028 Uiso 1 1 calc R . . C4 C 0.8329(4) 1.0158(3) 0.04481(9) 0.0226(7) Uani 1 1 d . . . H4 H 0.8618 1.0957 0.0557 0.027 Uiso 1 1 calc R . . C5 C 0.6682(4) 0.9824(3) 0.04660(9) 0.0196(7) Uani 1 1 d . . . C6 C 0.6221(4) 0.8528(3) 0.04940(9) 0.0191(7) Uani 1 1 d . . . H6A H 0.6949 0.8042 0.0349 0.023 Uiso 1 1 calc R . . H6B H 0.5156 0.8420 0.0361 0.023 Uiso 1 1 calc R . . C7 C 0.6246(4) 0.8082(3) 0.09238(9) 0.0172(7) Uani 1 1 d . . . H7 H 0.5718 0.8690 0.1081 0.021 Uiso 1 1 calc R . . C8 C 0.7811(4) 0.7757(3) 0.11579(9) 0.0182(7) Uani 1 1 d . . . H8 H 0.7540 0.7636 0.1438 0.022 Uiso 1 1 calc R . . C9 C 0.8577(4) 0.6585(3) 0.10451(10) 0.0228(7) Uani 1 1 d . . . H9A H 0.9132 0.6246 0.1288 0.027 Uiso 1 1 calc R . . H9B H 0.7736 0.6025 0.0953 0.027 Uiso 1 1 calc R . . C10 C 0.9730(4) 0.6667(3) 0.07248(10) 0.0244(8) Uani 1 1 d . . . H10A H 0.9160 0.6866 0.0466 0.029 Uiso 1 1 calc R . . H10B H 1.0251 0.5893 0.0698 0.029 Uiso 1 1 calc R . . C11 C 1.0959(4) 0.7618(3) 0.08377(10) 0.0240(8) Uani 1 1 d . . . H11A H 1.1543 0.7402 0.1093 0.029 Uiso 1 1 calc R . . H11B H 1.1714 0.7651 0.0632 0.029 Uiso 1 1 calc R . . C12 C 1.1425(4) 0.9714(3) 0.10821(10) 0.0241(8) Uani 1 1 d . . . H12A H 1.2455 0.9627 0.0973 0.029 Uiso 1 1 calc R . . H12B H 1.1064 1.0541 0.1043 0.029 Uiso 1 1 calc R . . C13 C 1.1530(4) 0.9379(3) 0.15211(10) 0.0247(8) Uani 1 1 d . . . H13A H 1.1819 1.0074 0.1690 0.030 Uiso 1 1 calc R . . H13B H 1.2320 0.8750 0.1579 0.030 Uiso 1 1 calc R . . C14 C 0.9892(4) 0.8935(3) 0.15955(9) 0.0183(7) Uani 1 1 d . . . C15 C 0.9343(4) 0.8095(3) 0.21949(10) 0.0280(8) Uani 1 1 d . . . H15A H 1.0001 0.7746 0.2421 0.034 Uiso 1 1 calc R . . H15B H 0.8272 0.7767 0.2192 0.034 Uiso 1 1 calc R . . C16 C 0.9323(4) 0.9423(3) 0.22225(10) 0.0268(8) Uani 1 1 d . . . H16A H 0.8476 0.9703 0.2381 0.032 Uiso 1 1 calc R . . H16B H 1.0338 0.9734 0.2340 0.032 Uiso 1 1 calc R . . C17 C 0.5550(4) 1.0698(3) 0.06142(10) 0.0245(8) Uani 1 1 d . . . H17A H 0.5920 1.1503 0.0569 0.037 Uiso 1 1 calc R . . H17B H 0.5472 1.0575 0.0899 0.037 Uiso 1 1 calc R . . H17C H 0.4519 1.0587 0.0471 0.037 Uiso 1 1 calc R . . C18 C 0.4630(3) 0.6698(3) 0.12301(9) 0.0166(7) Uani 1 1 d . . . C19 C 0.3849(4) 0.5510(3) 0.11574(9) 0.0179(7) Uani 1 1 d . . . H19A H 0.3087 0.5548 0.0920 0.022 Uiso 1 1 calc R . . H19B H 0.4641 0.4900 0.1111 0.022 Uiso 1 1 calc R . . C20 C 0.2835(4) 0.3982(3) 0.15692(9) 0.0160(7) Uani 1 1 d . . . C21 C 0.1830(4) 0.3498(3) 0.12069(9) 0.0175(7) Uani 1 1 d . . . C22 C 0.0213(4) 0.3616(3) 0.11869(10) 0.0200(7) Uani 1 1 d . . . H22 H -0.0270 0.3881 0.1414 0.024 Uiso 1 1 calc R . . C23 C -0.0704(4) 0.3352(3) 0.08410(10) 0.0263(8) Uani 1 1 d . . . H23 H -0.1810 0.3424 0.0834 0.032 Uiso 1 1 calc R . . C24 C -0.0020(4) 0.2983(3) 0.05038(10) 0.0259(8) Uani 1 1 d . . . H24 H -0.0646 0.2838 0.0263 0.031 Uiso 1 1 calc R . . C25 C 0.1583(4) 0.2830(3) 0.05233(10) 0.0266(8) Uani 1 1 d . . . H25 H 0.2058 0.2546 0.0297 0.032 Uiso 1 1 calc R . . C26 C 0.2504(4) 0.3087(3) 0.08705(9) 0.0223(7) Uani 1 1 d . . . H26 H 0.3606 0.2982 0.0879 0.027 Uiso 1 1 calc R . . C27 C 0.1988(3) 0.3949(3) 0.19520(9) 0.0149(6) Uani 1 1 d . . . C28 C 0.1472(4) 0.4983(3) 0.21199(9) 0.0195(7) Uani 1 1 d . . . H28 H 0.1618 0.5722 0.1995 0.023 Uiso 1 1 calc R . . C29 C 0.0739(4) 0.4933(3) 0.24737(9) 0.0219(7) Uani 1 1 d . . . H29 H 0.0384 0.5643 0.2587 0.026 Uiso 1 1 calc R . . C30 C 0.0521(4) 0.3872(3) 0.26618(9) 0.0207(7) Uani 1 1 d . . . H30 H 0.0031 0.3847 0.2904 0.025 Uiso 1 1 calc R . . C31 C 0.1028(4) 0.2841(3) 0.24924(10) 0.0230(7) Uani 1 1 d . . . H31 H 0.0884 0.2103 0.2619 0.028 Uiso 1 1 calc R . . C32 C 0.1742(4) 0.2875(3) 0.21404(10) 0.0210(7) Uani 1 1 d . . . H32 H 0.2069 0.2160 0.2025 0.025 Uiso 1 1 calc R . . C33 C 0.4431(4) 0.3370(3) 0.16507(9) 0.0176(7) Uani 1 1 d . . . C34 C 0.4608(4) 0.2150(3) 0.16017(9) 0.0203(7) Uani 1 1 d . . . H34 H 0.3738 0.1683 0.1504 0.024 Uiso 1 1 calc R . . C35 C 0.6056(4) 0.1617(3) 0.16960(10) 0.0240(7) Uani 1 1 d . . . H35 H 0.6168 0.0789 0.1662 0.029 Uiso 1 1 calc R . . C36 C 0.7336(4) 0.2287(3) 0.18398(10) 0.0243(8) Uani 1 1 d . . . H36 H 0.8324 0.1921 0.1902 0.029 Uiso 1 1 calc R . . C37 C 0.7162(4) 0.3491(3) 0.18923(9) 0.0229(7) Uani 1 1 d . . . H37 H 0.8031 0.3958 0.1990 0.027 Uiso 1 1 calc R . . C38 C 0.5712(4) 0.4016(3) 0.18012(9) 0.0187(7) Uani 1 1 d . . . H38 H 0.5599 0.4841 0.1843 0.022 Uiso 1 1 calc R . . Cl1 Cl 0.6107(9) 0.4197(7) 0.0154(2) 0.150(3) Uani 0.50 1 d PDU . . Cl2 Cl 0.4294(5) 0.6141(4) -0.01585(13) 0.0466(8) Uani 0.50 1 d PDU . . C39 C 0.4260(12) 0.4670(7) -0.0058(3) 0.054(2) Uani 0.50 1 d PDU . . H39A H 0.3979 0.4226 -0.0307 0.065 Uiso 0.50 1 calc PR . . H39B H 0.3456 0.4506 0.0129 0.065 Uiso 0.50 1 calc PR . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0237(13) 0.0274(14) 0.0221(12) 0.0090(10) -0.0001(9) -0.0053(10) O2 0.0246(13) 0.0215(13) 0.0250(12) -0.0037(10) 0.0063(10) -0.0053(10) O3 0.0211(12) 0.0143(11) 0.0205(11) 0.0023(9) 0.0024(9) -0.0065(9) O4 0.0210(12) 0.0113(11) 0.0230(11) -0.0006(9) 0.0067(9) -0.0025(9) O5 0.0283(13) 0.0191(12) 0.0205(11) -0.0022(9) 0.0000(9) 0.0060(10) O6 0.0282(13) 0.0152(12) 0.0226(12) 0.0027(9) 0.0005(10) 0.0026(10) C1 0.0132(16) 0.0119(16) 0.0198(15) 0.0021(12) 0.0008(12) 0.0010(12) C2 0.0126(16) 0.0163(17) 0.0265(17) -0.0012(13) 0.0030(13) -0.0030(13) C3 0.0215(18) 0.0237(19) 0.0250(17) 0.0015(14) 0.0069(14) -0.0074(14) C4 0.0258(18) 0.0199(18) 0.0216(16) 0.0051(14) -0.0005(13) -0.0046(14) C5 0.0209(17) 0.0191(17) 0.0180(16) 0.0047(13) -0.0025(13) -0.0009(14) C6 0.0191(17) 0.0171(17) 0.0209(16) -0.0002(13) 0.0005(13) -0.0021(13) C7 0.0178(16) 0.0094(15) 0.0248(16) -0.0013(12) 0.0038(13) -0.0043(12) C8 0.0167(16) 0.0153(16) 0.0226(16) 0.0020(13) 0.0016(13) -0.0012(13) C9 0.0210(18) 0.0164(17) 0.0302(18) -0.0019(14) -0.0033(14) -0.0010(14) C10 0.0259(19) 0.0194(18) 0.0277(18) -0.0057(14) 0.0003(14) 0.0045(15) C11 0.0175(17) 0.028(2) 0.0264(18) -0.0018(14) 0.0021(13) 0.0027(14) C12 0.0171(17) 0.0238(19) 0.0310(18) 0.0025(15) -0.0002(14) -0.0046(14) C13 0.0195(18) 0.0226(18) 0.0313(19) -0.0028(15) -0.0026(14) -0.0046(14) C14 0.0178(17) 0.0138(16) 0.0230(16) 0.0009(13) -0.0002(13) 0.0021(13) C15 0.035(2) 0.028(2) 0.0215(17) 0.0063(14) 0.0036(15) 0.0021(16) C16 0.032(2) 0.028(2) 0.0201(17) -0.0028(14) -0.0005(14) 0.0052(16) C17 0.0258(19) 0.0174(17) 0.0295(18) 0.0040(14) -0.0021(14) 0.0005(14) C18 0.0137(16) 0.0186(17) 0.0176(16) 0.0010(13) 0.0009(12) 0.0034(13) C19 0.0178(16) 0.0142(16) 0.0218(16) 0.0027(13) 0.0020(13) -0.0013(13) C20 0.0186(17) 0.0088(15) 0.0206(16) 0.0029(12) 0.0021(13) -0.0018(13) C21 0.0180(17) 0.0099(15) 0.0246(17) 0.0023(13) 0.0014(13) -0.0028(13) C22 0.0199(17) 0.0139(16) 0.0262(17) 0.0007(13) 0.0022(13) -0.0016(13) C23 0.0214(18) 0.0226(19) 0.0338(19) 0.0047(15) -0.0038(15) -0.0029(15) C24 0.036(2) 0.0170(18) 0.0231(17) 0.0021(14) -0.0051(15) -0.0090(15) C25 0.036(2) 0.0229(19) 0.0210(17) -0.0045(14) 0.0046(15) -0.0082(16) C26 0.0231(18) 0.0194(18) 0.0251(17) -0.0006(13) 0.0050(14) -0.0045(14) C27 0.0087(15) 0.0149(16) 0.0208(16) -0.0007(12) -0.0009(12) -0.0014(12) C28 0.0216(17) 0.0128(16) 0.0243(17) 0.0013(13) 0.0025(13) -0.0020(13) C29 0.0252(18) 0.0181(17) 0.0230(17) -0.0038(14) 0.0051(14) 0.0005(14) C30 0.0166(17) 0.0268(19) 0.0187(16) 0.0017(14) 0.0017(13) -0.0029(14) C31 0.0186(17) 0.0208(18) 0.0300(18) 0.0087(14) 0.0033(14) 0.0008(14) C32 0.0218(18) 0.0154(17) 0.0264(17) 0.0005(13) 0.0049(14) 0.0030(14) C33 0.0181(17) 0.0158(16) 0.0193(16) 0.0004(13) 0.0041(12) -0.0005(13) C34 0.0229(18) 0.0167(17) 0.0213(16) -0.0005(13) 0.0024(13) -0.0021(14) C35 0.0293(19) 0.0172(17) 0.0262(17) 0.0008(14) 0.0068(14) 0.0048(15) C36 0.0206(18) 0.028(2) 0.0248(17) 0.0023(15) 0.0041(14) 0.0058(15) C37 0.0187(17) 0.0271(19) 0.0228(17) -0.0014(14) 0.0016(13) -0.0011(14) C38 0.0208(17) 0.0174(17) 0.0182(16) 0.0001(13) 0.0036(13) 0.0012(14) Cl1 0.147(6) 0.134(6) 0.154(5) -0.008(4) -0.084(5) 0.082(5) Cl2 0.0424(15) 0.0430(16) 0.0519(16) 0.0176(12) -0.0104(12) -0.0054(12) C39 0.086(7) 0.029(5) 0.047(5) 0.003(4) -0.001(5) -0.012(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C5 1.448(4) . ? O1 C4 1.457(4) . ? O2 C18 1.192(4) . ? O3 C18 1.342(4) . ? O3 C7 1.461(4) . ? O4 C19 1.409(4) . ? O4 C20 1.445(4) . ? O5 C16 1.419(4) . ? O5 C14 1.424(4) . ? O6 C15 1.426(4) . ? O6 C14 1.430(4) . ? C1 C8 1.543(4) . ? C1 C2 1.544(4) . ? C1 C14 1.547(4) . ? C1 H1 1.0000 . ? C2 C11 1.532(5) . ? C2 C3 1.537(5) . ? C2 C12 1.549(4) . ? C3 C4 1.496(5) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.468(5) . ? C4 H4 1.0000 . ? C5 C17 1.501(5) . ? C5 C6 1.523(4) . ? C6 C7 1.533(4) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.543(4) . ? C7 H7 1.0000 . ? C8 C9 1.540(4) . ? C8 H8 1.0000 . ? C9 C10 1.528(5) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.532(5) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C13 1.524(5) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.532(5) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C15 C16 1.505(5) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 C19 1.513(4) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 C27 1.534(4) . ? C20 C21 1.535(4) . ? C20 C33 1.538(4) . ? C21 C22 1.389(4) . ? C21 C26 1.396(4) . ? C22 C23 1.383(5) . ? C22 H22 0.9500 . ? C23 C24 1.387(5) . ? C23 H23 0.9500 . ? C24 C25 1.382(5) . ? C24 H24 0.9500 . ? C25 C26 1.387(5) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? C27 C28 1.388(4) . ? C27 C32 1.395(4) . ? C28 C29 1.397(4) . ? C28 H28 0.9500 . ? C29 C30 1.377(5) . ? C29 H29 0.9500 . ? C30 C31 1.384(5) . ? C30 H30 0.9500 . ? C31 C32 1.382(5) . ? C31 H31 0.9500 . ? C32 H32 0.9500 . ? C33 C38 1.380(5) . ? C33 C34 1.400(4) . ? C34 C35 1.392(5) . ? C34 H34 0.9500 . ? C35 C36 1.387(5) . ? C35 H35 0.9500 . ? C36 C37 1.383(5) . ? C36 H36 0.9500 . ? C37 C38 1.389(5) . ? C37 H37 0.9500 . ? C38 H38 0.9500 . ? Cl1 C39 1.765(11) . ? Cl2 C39 1.699(9) . ? C39 H39A 0.9900 . ? C39 H39B 0.9900 . ? 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 C5 O1 C4 60.70(19) . . ? C18 O3 C7 116.4(2) . . ? C19 O4 C20 116.3(2) . . ? C16 O5 C14 106.5(2) . . ? C15 O6 C14 108.5(2) . . ? C8 C1 C2 117.8(3) . . ? C8 C1 C14 113.7(2) . . ? C2 C1 C14 105.6(2) . . ? C8 C1 H1 106.3 . . ? C2 C1 H1 106.3 . . ? C14 C1 H1 106.3 . . ? C11 C2 C3 108.4(3) . . ? C11 C2 C1 110.3(3) . . ? C3 C2 C1 115.6(3) . . ? C11 C2 C12 110.4(3) . . ? C3 C2 C12 110.6(3) . . ? C1 C2 C12 101.3(2) . . ? C4 C3 C2 115.1(3) . . ? C4 C3 H3A 108.5 . . ? C2 C3 H3A 108.5 . . ? C4 C3 H3B 108.5 . . ? C2 C3 H3B 108.5 . . ? H3A C3 H3B 107.5 . . ? O1 C4 C5 59.33(19) . . ? O1 C4 C3 116.3(3) . . ? C5 C4 C3 123.4(3) . . ? O1 C4 H4 115.3 . . ? C5 C4 H4 115.3 . . ? C3 C4 H4 115.3 . . ? O1 C5 C4 59.97(19) . . ? O1 C5 C17 113.4(3) . . ? C4 C5 C17 119.7(3) . . ? O1 C5 C6 114.4(3) . . ? C4 C5 C6 120.4(3) . . ? C17 C5 C6 115.8(3) . . ? C5 C6 C7 113.0(3) . . ? C5 C6 H6A 109.0 . . ? C7 C6 H6A 109.0 . . ? C5 C6 H6B 109.0 . . ? C7 C6 H6B 109.0 . . ? H6A C6 H6B 107.8 . . ? O3 C7 C6 104.1(2) . . ? O3 C7 C8 108.5(2) . . ? C6 C7 C8 120.3(3) . . ? O3 C7 H7 107.8 . . ? C6 C7 H7 107.8 . . ? C8 C7 H7 107.8 . . ? C9 C8 C7 116.7(3) . . ? C9 C8 C1 112.6(3) . . ? C7 C8 C1 112.1(2) . . ? C9 C8 H8 104.7 . . ? C7 C8 H8 104.7 . . ? C1 C8 H8 104.7 . . ? C10 C9 C8 116.0(3) . . ? C10 C9 H9A 108.3 . . ? C8 C9 H9A 108.3 . . ? C10 C9 H9B 108.3 . . ? C8 C9 H9B 108.3 . . ? H9A C9 H9B 107.4 . . ? C9 C10 C11 109.8(3) . . ? C9 C10 H10A 109.7 . . ? C11 C10 H10A 109.7 . . ? C9 C10 H10B 109.7 . . ? C11 C10 H10B 109.7 . . ? H10A C10 H10B 108.2 . . ? C2 C11 C10 112.0(3) . . ? C2 C11 H11A 109.2 . . ? C10 C11 H11A 109.2 . . ? C2 C11 H11B 109.2 . . ? C10 C11 H11B 109.2 . . ? H11A C11 H11B 107.9 . . ? C13 C12 C2 104.8(3) . . ? C13 C12 H12A 110.8 . . ? C2 C12 H12A 110.8 . . ? C13 C12 H12B 110.8 . . ? C2 C12 H12B 110.8 . . ? H12A C12 H12B 108.9 . . ? C12 C13 C14 105.1(3) . . ? C12 C13 H13A 110.7 . . ? C14 C13 H13A 110.7 . . ? C12 C13 H13B 110.7 . . ? C14 C13 H13B 110.7 . . ? H13A C13 H13B 108.8 . . ? O5 C14 O6 105.5(2) . . ? O5 C14 C13 113.0(3) . . ? O6 C14 C13 110.4(3) . . ? O5 C14 C1 106.9(2) . . ? O6 C14 C1 114.3(2) . . ? C13 C14 C1 106.8(3) . . ? O6 C15 C16 103.7(3) . . ? O6 C15 H15A 111.0 . . ? C16 C15 H15A 111.0 . . ? O6 C15 H15B 111.0 . . ? C16 C15 H15B 111.0 . . ? H15A C15 H15B 109.0 . . ? O5 C16 C15 101.6(3) . . ? O5 C16 H16A 111.4 . . ? C15 C16 H16A 111.4 . . ? O5 C16 H16B 111.4 . . ? C15 C16 H16B 111.4 . . ? H16A C16 H16B 109.3 . . ? C5 C17 H17A 109.5 . . ? C5 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C5 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? O2 C18 O3 125.9(3) . . ? O2 C18 C19 125.7(3) . . ? O3 C18 C19 108.3(2) . . ? O4 C19 C18 107.6(2) . . ? O4 C19 H19A 110.2 . . ? C18 C19 H19A 110.2 . . ? O4 C19 H19B 110.2 . . ? C18 C19 H19B 110.2 . . ? H19A C19 H19B 108.5 . . ? O4 C20 C27 104.5(2) . . ? O4 C20 C21 107.1(2) . . ? C27 C20 C21 112.8(2) . . ? O4 C20 C33 109.2(2) . . ? C27 C20 C33 108.4(2) . . ? C21 C20 C33 114.4(3) . . ? C22 C21 C26 118.2(3) . . ? C22 C21 C20 119.7(3) . . ? C26 C21 C20 121.5(3) . . ? C23 C22 C21 121.0(3) . . ? C23 C22 H22 119.5 . . ? C21 C22 H22 119.5 . . ? C22 C23 C24 120.5(3) . . ? C22 C23 H23 119.8 . . ? C24 C23 H23 119.8 . . ? C25 C24 C23 119.1(3) . . ? C25 C24 H24 120.4 . . ? C23 C24 H24 120.4 . . ? C24 C25 C26 120.5(3) . . ? C24 C25 H25 119.8 . . ? C26 C25 H25 119.8 . . ? C25 C26 C21 120.7(3) . . ? C25 C26 H26 119.7 . . ? C21 C26 H26 119.7 . . ? C28 C27 C32 118.8(3) . . ? C28 C27 C20 120.9(3) . . ? C32 C27 C20 120.3(3) . . ? C27 C28 C29 119.8(3) . . ? C27 C28 H28 120.1 . . ? C29 C28 H28 120.1 . . ? C30 C29 C28 121.1(3) . . ? C30 C29 H29 119.4 . . ? C28 C29 H29 119.4 . . ? C29 C30 C31 119.0(3) . . ? C29 C30 H30 120.5 . . ? C31 C30 H30 120.5 . . ? C32 C31 C30 120.5(3) . . ? C32 C31 H31 119.7 . . ? C30 C31 H31 119.7 . . ? C31 C32 C27 120.7(3) . . ? C31 C32 H32 119.6 . . ? C27 C32 H32 119.6 . . ? C38 C33 C34 118.4(3) . . ? C38 C33 C20 119.7(3) . . ? C34 C33 C20 121.8(3) . . ? C35 C34 C33 120.2(3) . . ? C35 C34 H34 119.9 . . ? C33 C34 H34 119.9 . . ? C36 C35 C34 120.5(3) . . ? C36 C35 H35 119.7 . . ? C34 C35 H35 119.7 . . ? C37 C36 C35 119.4(3) . . ? C37 C36 H36 120.3 . . ? C35 C36 H36 120.3 . . ? C36 C37 C38 119.8(3) . . ? C36 C37 H37 120.1 . . ? C38 C37 H37 120.1 . . ? C33 C38 C37 121.6(3) . . ? C33 C38 H38 119.2 . . ? C37 C38 H38 119.2 . . ? Cl2 C39 Cl1 110.4(6) . . ? Cl2 C39 H39A 109.6 . . ? Cl1 C39 H39A 109.6 . . ? Cl2 C39 H39B 109.6 . . ? Cl1 C39 H39B 109.6 . . ? H39A C39 H39B 108.1 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C8 C1 C2 C11 -45.1(4) . . . . ? C14 C1 C2 C11 83.1(3) . . . . ? C8 C1 C2 C3 78.3(4) . . . . ? C14 C1 C2 C3 -153.4(3) . . . . ? C8 C1 C2 C12 -162.1(3) . . . . ? C14 C1 C2 C12 -33.8(3) . . . . ? C11 C2 C3 C4 154.8(3) . . . . ? C1 C2 C3 C4 30.4(4) . . . . ? C12 C2 C3 C4 -84.0(3) . . . . ? C5 O1 C4 C3 114.9(3) . . . . ? C2 C3 C4 O1 -150.3(3) . . . . ? C2 C3 C4 C5 -81.1(4) . . . . ? C4 O1 C5 C17 112.0(3) . . . . ? C4 O1 C5 C6 -112.3(3) . . . . ? C3 C4 C5 O1 -103.1(3) . . . . ? O1 C4 C5 C17 -101.4(3) . . . . ? C3 C4 C5 C17 155.5(3) . . . . ? O1 C4 C5 C6 102.3(3) . . . . ? C3 C4 C5 C6 -0.7(5) . . . . ? O1 C5 C6 C7 157.4(3) . . . . ? C4 C5 C6 C7 89.2(4) . . . . ? C17 C5 C6 C7 -68.0(4) . . . . ? C18 O3 C7 C6 -157.8(3) . . . . ? C18 O3 C7 C8 73.0(3) . . . . ? C5 C6 C7 O3 159.6(2) . . . . ? C5 C6 C7 C8 -78.7(4) . . . . ? O3 C7 C8 C9 45.0(3) . . . . ? C6 C7 C8 C9 -74.5(4) . . . . ? O3 C7 C8 C1 176.9(2) . . . . ? C6 C7 C8 C1 57.4(4) . . . . ? C2 C1 C8 C9 37.2(4) . . . . ? C14 C1 C8 C9 -87.1(3) . . . . ? C2 C1 C8 C7 -96.8(3) . . . . ? C14 C1 C8 C7 138.9(3) . . . . ? C7 C8 C9 C10 91.0(3) . . . . ? C1 C8 C9 C10 -40.7(4) . . . . ? C8 C9 C10 C11 52.4(4) . . . . ? C3 C2 C11 C10 -71.4(3) . . . . ? C1 C2 C11 C10 56.1(4) . . . . ? C12 C2 C11 C10 167.2(3) . . . . ? C9 C10 C11 C2 -60.2(4) . . . . ? C11 C2 C12 C13 -76.0(3) . . . . ? C3 C2 C12 C13 163.9(3) . . . . ? C1 C2 C12 C13 40.8(3) . . . . ? C2 C12 C13 C14 -32.2(3) . . . . ? C16 O5 C14 O6 27.6(3) . . . . ? C16 O5 C14 C13 -93.1(3) . . . . ? C16 O5 C14 C1 149.7(3) . . . . ? C15 O6 C14 O5 -5.1(3) . . . . ? C15 O6 C14 C13 117.3(3) . . . . ? C15 O6 C14 C1 -122.3(3) . . . . ? C12 C13 C14 O5 -106.7(3) . . . . ? C12 C13 C14 O6 135.4(3) . . . . ? C12 C13 C14 C1 10.6(3) . . . . ? C8 C1 C14 O5 -93.2(3) . . . . ? C2 C1 C14 O5 136.2(3) . . . . ? C8 C1 C14 O6 23.2(4) . . . . ? C2 C1 C14 O6 -107.4(3) . . . . ? C8 C1 C14 C13 145.6(3) . . . . ? C2 C1 C14 C13 15.0(3) . . . . ? C14 O6 C15 C16 -17.5(3) . . . . ? C14 O5 C16 C15 -37.6(3) . . . . ? O6 C15 C16 O5 33.4(3) . . . . ? C7 O3 C18 O2 7.0(4) . . . . ? C7 O3 C18 C19 -171.7(2) . . . . ? C20 O4 C19 C18 -154.7(2) . . . . ? O2 C18 C19 O4 6.8(4) . . . . ? O3 C18 C19 O4 -174.5(2) . . . . ? C19 O4 C20 C27 -180.0(2) . . . . ? C19 O4 C20 C21 -60.1(3) . . . . ? C19 O4 C20 C33 64.2(3) . . . . ? O4 C20 C21 C22 -83.9(3) . . . . ? C27 C20 C21 C22 30.5(4) . . . . ? C33 C20 C21 C22 155.0(3) . . . . ? O4 C20 C21 C26 87.1(3) . . . . ? C27 C20 C21 C26 -158.5(3) . . . . ? C33 C20 C21 C26 -34.0(4) . . . . ? C26 C21 C22 C23 -1.1(5) . . . . ? C20 C21 C22 C23 170.2(3) . . . . ? C21 C22 C23 C24 -1.2(5) . . . . ? C22 C23 C24 C25 3.0(5) . . . . ? C23 C24 C25 C26 -2.6(5) . . . . ? C24 C25 C26 C21 0.4(5) . . . . ? C22 C21 C26 C25 1.4(5) . . . . ? C20 C21 C26 C25 -169.7(3) . . . . ? O4 C20 C27 C28 7.5(4) . . . . ? C21 C20 C27 C28 -108.4(3) . . . . ? C33 C20 C27 C28 123.8(3) . . . . ? O4 C20 C27 C32 -171.6(3) . . . . ? C21 C20 C27 C32 72.5(4) . . . . ? C33 C20 C27 C32 -55.3(4) . . . . ? C32 C27 C28 C29 0.7(5) . . . . ? C20 C27 C28 C29 -178.4(3) . . . . ? C27 C28 C29 C30 0.3(5) . . . . ? C28 C29 C30 C31 -0.7(5) . . . . ? C29 C30 C31 C32 0.0(5) . . . . ? C30 C31 C32 C27 1.0(5) . . . . ? C28 C27 C32 C31 -1.4(5) . . . . ? C20 C27 C32 C31 177.8(3) . . . . ? O4 C20 C33 C38 25.7(4) . . . . ? C27 C20 C33 C38 -87.6(3) . . . . ? C21 C20 C33 C38 145.6(3) . . . . ? O4 C20 C33 C34 -158.7(3) . . . . ? C27 C20 C33 C34 88.1(3) . . . . ? C21 C20 C33 C34 -38.7(4) . . . . ? C38 C33 C34 C35 -1.3(5) . . . . ? C20 C33 C34 C35 -177.0(3) . . . . ? C33 C34 C35 C36 0.1(5) . . . . ? C34 C35 C36 C37 0.6(5) . . . . ? C35 C36 C37 C38 0.0(5) . . . . ? C34 C33 C38 C37 1.9(5) . . . . ? C20 C33 C38 C37 177.7(3) . . . . ? C36 C37 C38 C33 -1.3(5) . . . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 25.35 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.371 _refine_diff_density_min -0.311 _refine_diff_density_rms 0.064