data_cd26176 _publ_contact_author_name 'Jian-Min Yue' _publ_contact_author_address ; State Key Laboratory of Drug Research, Institute of Materia Medica, Shanghai Institutes for Biological Sciences, Chinese Academy of Sciences, 555 Zuchongzhi Road, Zhangjiang Hi-Tech Park, Shanghai 201203 P.R.China ; _publ_contact_author_email jmyue@mail.shcnc.ac.cn _publ_contact_author_phone +862150806718 _publ_contact_author_fax +862150806718 loop_ _publ_author_name ; Xiao-ning Wang, Sheng Yin, Cheng-Qi Fan, Fang-Dao Wang, Li-Ping Lin, Jian Ding, Jian-Min Yue ; _journal_name_full 'Organic Letters' _publ_section_title ; Turrapubesins A and B, First Examples of Halogenated and Maleimide-bearing Limonoids in Nature from Turraea pubescens ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'Turrapubesin A' _chemical_melting_point 454 _chemical_formula_moiety ? _chemical_formula_sum 'C31 H39 Cl O9' _chemical_formula_weight 591.07 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) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 10.5361(10) _cell_length_b 11.1344(10) _cell_length_c 13.6933(12) _cell_angle_alpha 90.00 _cell_angle_beta 108.7020(10) _cell_angle_gamma 90.00 _cell_volume 1521.6(2) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3217 _cell_measurement_theta_min 4.821 _cell_measurement_theta_max 52.000 _exptl_crystal_preparation methanol _exptl_crystal_description prismatic _exptl_crystal_colour colorless _exptl_crystal_size_max 0.506 _exptl_crystal_size_mid 0.485 _exptl_crystal_size_min 0.347 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.290 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 628 _exptl_absorpt_coefficient_mu 0.178 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.7689 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8668 _diffrn_reflns_av_R_equivalents 0.0473 _diffrn_reflns_av_sigmaI/netI 0.0490 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.04 _diffrn_reflns_theta_max 26.49 _reflns_number_total 5363 _reflns_number_gt 4073 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1047P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.008(3) _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 0.04(13) _chemical_absolute_configuration ad _refine_ls_number_reflns 5363 _refine_ls_number_parameters 382 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0703 _refine_ls_R_factor_gt 0.0585 _refine_ls_wR_factor_ref 0.1680 _refine_ls_wR_factor_gt 0.1598 _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_restrained_S_all 1.030 _refine_ls_shift/su_max 0.094 _refine_ls_shift/su_mean 0.008 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 Cl1 Cl 0.3613(2) 0.2893(4) 0.18126(13) 0.1332(19) Uani 1 1 d . . . O1 O 0.0231(4) -0.0825(3) 0.6154(3) 0.0951(10) Uani 1 1 d . . . O2 O 0.0203(3) 0.4522(2) 0.1923(2) 0.0750(8) Uani 1 1 d . . . O3 O -0.4867(4) 0.0726(5) -0.0678(4) 0.1038(16) Uani 1 1 d . . . O4 O 0.5636(4) 0.1012(5) 0.4413(3) 0.1042(15) Uani 1 1 d . . . O5 O 0.4748(3) -0.0800(4) 0.3992(2) 0.0834(9) Uani 1 1 d . . . O6 O 0.1389(2) -0.11284(18) 0.29829(15) 0.0479(5) Uani 1 1 d . . . O7 O 0.2333(4) -0.1920(3) 0.1888(3) 0.0990(11) Uani 1 1 d . . . O8 O -0.0881(2) -0.07815(19) 0.14260(15) 0.0448(5) Uani 1 1 d . . . O9 O -0.1791(3) -0.1385(3) 0.2618(2) 0.0820(9) Uani 1 1 d . . . C1 C 0.0565(3) 0.1171(3) 0.4259(2) 0.0501(8) Uani 1 1 d . . . H1 H 0.0005 0.1694 0.3784 0.060 Uiso 1 1 calc R . . C2 C 0.0014(4) 0.0536(4) 0.4832(3) 0.0586(9) Uani 1 1 d . . . H2 H -0.0904 0.0599 0.4710 0.070 Uiso 1 1 calc R . . C3 C 0.0784(4) -0.0250(3) 0.5637(3) 0.0607(10) Uani 1 1 d . . . C4 C 0.2290(4) -0.0303(3) 0.5904(2) 0.0545(8) Uani 1 1 d . . . C5 C 0.2762(3) 0.0062(3) 0.4974(2) 0.0466(7) Uani 1 1 d . . . H5 H 0.2592 -0.0639 0.4516 0.056 Uiso 1 1 calc R . . C6 C 0.4290(4) 0.0242(4) 0.5344(3) 0.0665(10) Uani 1 1 d . . . H6A H 0.4484 0.1004 0.5704 0.080 Uiso 1 1 calc R . . H6B H 0.4689 -0.0382 0.5842 0.080 Uiso 1 1 calc R . . C7 C 0.4969(4) 0.0229(6) 0.4537(3) 0.0791(13) Uani 1 1 d . . . C8 C 0.1663(3) 0.2193(3) 0.2525(2) 0.0469(7) Uani 1 1 d . . . C9 C 0.2035(3) 0.1030(3) 0.3143(2) 0.0409(6) Uani 1 1 d . . . H9 H 0.2975 0.0874 0.3210 0.049 Uiso 1 1 calc R . . C10 C 0.1982(3) 0.1135(3) 0.4295(2) 0.0434(7) Uani 1 1 d . . . C11 C 0.1218(3) 0.0007(2) 0.2458(2) 0.0389(6) Uani 1 1 d . . . H11 H 0.1551 -0.0085 0.1870 0.047 Uiso 1 1 calc R . . C12 C -0.0270(3) 0.0248(3) 0.20278(19) 0.0381(6) Uani 1 1 d . . . H12 H -0.0639 0.0366 0.2593 0.046 Uiso 1 1 calc R . . C13 C -0.0540(3) 0.1347(3) 0.1338(2) 0.0393(6) Uani 1 1 d . . . C14 C 0.0473(3) 0.2329(3) 0.1798(2) 0.0462(7) Uani 1 1 d . . . C15 C -0.0115(4) 0.3505(3) 0.1273(3) 0.0598(9) Uani 1 1 d . . . H15 H 0.0231 0.3640 0.0697 0.072 Uiso 1 1 calc R . . C16 C -0.1618(4) 0.3268(4) 0.0827(3) 0.0685(11) Uani 1 1 d . . . H16A H -0.1899 0.3271 0.0079 0.082 Uiso 1 1 calc R . . H16B H -0.2116 0.3883 0.1051 0.082 Uiso 1 1 calc R . . C17 C -0.1872(3) 0.2027(3) 0.1226(2) 0.0548(9) Uani 1 1 d . . . H17 H -0.1923 0.2144 0.1922 0.066 Uiso 1 1 calc R . . C18 C -0.0432(3) 0.1052(3) 0.0266(2) 0.0469(7) Uani 1 1 d . . . H18A H 0.0416 0.0678 0.0346 0.070 Uiso 1 1 calc R . . H18B H -0.0503 0.1779 -0.0124 0.070 Uiso 1 1 calc R . . H18C H -0.1142 0.0515 -0.0091 0.070 Uiso 1 1 calc R . . C19 C 0.2555(4) 0.2355(4) 0.4765(3) 0.0661(10) Uani 1 1 d . . . H19A H 0.2031 0.2992 0.4358 0.099 Uiso 1 1 calc R . . H19B H 0.3467 0.2425 0.4773 0.099 Uiso 1 1 calc R . . H19C H 0.2525 0.2407 0.5457 0.099 Uiso 1 1 calc R . . C20 C -0.3136(4) 0.1410(4) 0.0606(3) 0.0672(11) Uani 1 1 d . . . C21 C -0.3750(4) 0.1413(5) -0.0399(3) 0.0917(15) Uani 1 1 d . . . H21 H -0.3448 0.1842 -0.0865 0.110 Uiso 1 1 calc R . . C22 C -0.3904(5) 0.0664(8) 0.0992(5) 0.116(3) Uani 1 1 d . . . H22 H -0.3713 0.0466 0.1684 0.123 Uiso 1 1 calc R . . C23 C -0.4934(5) 0.0278(8) 0.0250(7) 0.117(3) Uani 1 1 d . . . H23 H -0.5605 -0.0217 0.0327 0.126 Uiso 1 1 calc R . . C28 C 0.2753(6) -0.1587(5) 0.6211(4) 0.0945(16) Uani 1 1 d . . . H28A H 0.2394 -0.1859 0.6734 0.122 Uiso 1 1 calc R . . H28B H 0.3714 -0.1610 0.6473 0.122 Uiso 1 1 calc R . . H28C H 0.2442 -0.2101 0.5618 0.122 Uiso 1 1 calc R . . C29 C 0.2826(5) 0.0517(5) 0.6868(3) 0.0866(14) Uani 1 1 d . . . H29A H 0.2448 0.1306 0.6709 0.130 Uiso 1 1 calc R . . H29B H 0.3785 0.0567 0.7062 0.130 Uiso 1 1 calc R . . H29C H 0.2577 0.0185 0.7427 0.130 Uiso 1 1 calc R . . C30 C 0.2752(4) 0.3125(4) 0.2700(4) 0.0834(13) Uani 1 1 d . . . H30A H 0.3368 0.3060 0.3398 0.100 Uiso 1 1 calc R . . H30B H 0.2362 0.3923 0.2612 0.100 Uiso 1 1 calc R . . C31 C 0.5376(6) -0.0837(7) 0.3194(4) 0.115(3) Uani 1 1 d . . . H31A H 0.4853 -0.0378 0.2610 0.128 Uiso 1 1 calc R . . H31B H 0.5431 -0.1655 0.2989 0.128 Uiso 1 1 calc R . . H31C H 0.6261 -0.0503 0.3454 0.128 Uiso 1 1 calc R . . C32 C 0.1926(4) -0.2022(4) 0.2611(3) 0.0669(10) Uani 1 1 d . . . C33 C 0.1992(7) -0.3137(4) 0.3213(4) 0.106(2) Uani 1 1 d . . . H33A H 0.2172 -0.3806 0.2835 0.129 Uiso 1 1 calc R . . H33B H 0.1152 -0.3260 0.3333 0.129 Uiso 1 1 calc R . . H33C H 0.2695 -0.3068 0.3862 0.129 Uiso 1 1 calc R . . C34 C -0.1604(4) -0.1537(4) 0.1813(3) 0.0600(9) Uani 1 1 d . . . C35 C -0.2121(6) -0.2558(5) 0.1093(4) 0.0975(17) Uani 1 1 d . . . H35A H -0.1457 -0.3181 0.1229 0.126 Uiso 1 1 calc R . . H35B H -0.2315 -0.2284 0.0395 0.126 Uiso 1 1 calc R . . H35C H -0.2924 -0.2866 0.1188 0.126 Uiso 1 1 calc R . . H3 H 0.008(5) 0.443(5) 0.257(4) 0.103(17) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.1001(17) 0.256(5) 0.0938(10) -0.0287(18) 0.0554(11) -0.107(3) O1 0.115(2) 0.097(2) 0.092(2) 0.0164(19) 0.059(2) -0.024(2) O2 0.120(2) 0.0350(14) 0.0684(17) -0.0028(13) 0.0277(16) -0.0013(14) O3 0.077(2) 0.132(4) 0.116(3) 0.002(3) -0.017(2) 0.000(2) O4 0.088(2) 0.135(4) 0.113(3) 0.020(3) 0.024(2) -0.046(3) O5 0.0784(19) 0.100(2) 0.0826(19) 0.024(2) 0.0413(16) 0.0225(18) O6 0.0618(13) 0.0366(11) 0.0385(10) 0.0006(9) 0.0064(9) -0.0025(9) O7 0.133(3) 0.081(2) 0.088(2) -0.0112(18) 0.042(2) 0.042(2) O8 0.0522(12) 0.0430(12) 0.0369(10) -0.0018(9) 0.0111(9) -0.0114(9) O9 0.101(2) 0.092(2) 0.0651(16) -0.0097(16) 0.0439(15) -0.0422(17) C1 0.0561(19) 0.0530(19) 0.0388(15) -0.0109(15) 0.0116(13) 0.0071(15) C2 0.0559(19) 0.073(2) 0.0514(18) -0.0093(18) 0.0230(15) -0.0024(17) C3 0.082(3) 0.060(2) 0.0479(18) -0.0071(18) 0.0306(18) -0.0088(19) C4 0.080(2) 0.0479(19) 0.0353(15) 0.0048(14) 0.0178(15) -0.0014(17) C5 0.0501(18) 0.0510(19) 0.0363(14) -0.0008(14) 0.0103(13) 0.0012(14) C6 0.060(2) 0.082(3) 0.0490(18) 0.006(2) 0.0054(16) 0.002(2) C7 0.040(2) 0.118(4) 0.069(2) 0.026(3) 0.0034(17) -0.007(2) C8 0.0552(19) 0.0410(18) 0.0423(15) 0.0009(14) 0.0126(14) -0.0096(14) C9 0.0403(15) 0.0411(16) 0.0395(14) 0.0005(13) 0.0105(11) -0.0093(12) C10 0.0492(16) 0.0383(16) 0.0376(14) -0.0016(13) 0.0068(12) -0.0045(13) C11 0.0459(16) 0.0341(16) 0.0360(14) 0.0028(12) 0.0124(12) 0.0035(12) C12 0.0414(15) 0.0425(16) 0.0298(12) -0.0047(12) 0.0105(11) -0.0066(13) C13 0.0425(15) 0.0439(17) 0.0304(13) -0.0017(12) 0.0100(11) 0.0027(12) C14 0.065(2) 0.0408(17) 0.0342(14) -0.0001(13) 0.0181(14) -0.0038(14) C15 0.094(3) 0.0406(18) 0.0447(17) 0.0035(15) 0.0221(17) 0.0063(18) C16 0.088(3) 0.057(2) 0.0499(19) 0.0008(18) 0.0079(18) 0.022(2) C17 0.058(2) 0.067(2) 0.0374(15) 0.0036(16) 0.0131(14) 0.0229(17) C18 0.0640(19) 0.0431(17) 0.0342(14) 0.0007(14) 0.0166(13) 0.0031(15) C19 0.087(3) 0.056(2) 0.0450(17) -0.0095(17) 0.0072(17) -0.0150(19) C20 0.047(2) 0.084(3) 0.065(2) 0.009(2) 0.0115(17) 0.0173(18) C21 0.064(3) 0.124(4) 0.067(3) 0.001(3) -0.007(2) -0.013(3) C22 0.059(3) 0.150(8) 0.117(4) 0.071(5) 0.012(3) -0.019(4) C23 0.054(3) 0.168(7) 0.182(7) 0.072(6) -0.014(4) -0.030(3) C28 0.133(4) 0.081(3) 0.079(3) 0.044(3) 0.047(3) 0.021(3) C29 0.117(4) 0.101(4) 0.0354(17) -0.010(2) 0.016(2) -0.024(3) C30 0.080(3) 0.070(3) 0.090(3) 0.020(2) 0.011(2) -0.025(2) C31 0.109(4) 0.189(7) 0.104(4) 0.057(5) 0.071(3) 0.059(5) C32 0.081(3) 0.048(2) 0.054(2) -0.0118(18) -0.0024(19) 0.0125(19) C33 0.153(5) 0.041(2) 0.092(3) 0.000(2) -0.005(3) 0.014(3) C34 0.062(2) 0.064(2) 0.0512(19) -0.0003(18) 0.0147(16) -0.0215(18) C35 0.135(4) 0.087(3) 0.070(3) -0.019(2) 0.033(3) -0.064(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 Cl1 C30 1.753(5) . ? O1 C3 1.231(4) . ? O2 C15 1.413(4) . ? O2 H3 0.95(5) . ? O3 C21 1.352(6) . ? O3 C23 1.387(8) . ? O4 C7 1.165(6) . ? O5 C7 1.346(6) . ? O5 C31 1.449(5) . ? O6 C32 1.325(4) . ? O6 C11 1.437(3) . ? O7 C32 1.203(5) . ? O8 C34 1.352(4) . ? O8 C12 1.438(3) . ? O9 C34 1.191(4) . ? C1 C2 1.321(5) . ? C1 C10 1.478(4) . ? C1 H1 0.9300 . ? C2 C3 1.437(5) . ? C2 H2 0.9300 . ? C3 C4 1.510(6) . ? C4 C28 1.526(6) . ? C4 C29 1.555(5) . ? C4 C5 1.563(4) . ? C5 C6 1.538(5) . ? C5 C10 1.574(4) . ? C5 H5 0.9800 . ? C6 C7 1.497(6) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C8 C14 1.336(5) . ? C8 C30 1.508(5) . ? C8 C9 1.528(4) . ? C9 C11 1.550(4) . ? C9 C10 1.600(4) . ? C9 H9 0.9800 . ? C10 C19 1.541(5) . ? C11 C12 1.512(4) . ? C11 H11 0.9800 . ? C12 C13 1.516(4) . ? C12 H12 0.9800 . ? C13 C14 1.517(4) . ? C13 C18 1.544(4) . ? C13 C17 1.559(4) . ? C14 C15 1.526(5) . ? C15 C16 1.527(6) . ? C15 H15 0.9800 . ? C16 C17 1.540(6) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 C20 1.497(6) . ? C17 H17 0.9800 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 C21 1.320(6) . ? C20 C22 1.377(7) . ? C21 H21 0.9300 . ? C22 C23 1.299(9) . ? C22 H22 0.9300 . ? C23 H23 0.9300 . ? C28 H28A 0.9600 . ? C28 H28B 0.9600 . ? C28 H28C 0.9600 . ? C29 H29A 0.9600 . ? C29 H29B 0.9600 . ? C29 H29C 0.9600 . ? C30 H30A 0.9700 . ? C30 H30B 0.9700 . ? C31 H31A 0.9600 . ? C31 H31B 0.9600 . ? C31 H31C 0.9600 . ? C32 C33 1.479(6) . ? C33 H33A 0.9600 . ? C33 H33B 0.9600 . ? C33 H33C 0.9600 . ? C34 C35 1.489(6) . ? C35 H35A 0.9600 . ? C35 H35B 0.9600 . ? C35 H35C 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 C15 O2 H3 116(4) . . ? C21 O3 C23 103.9(4) . . ? C7 O5 C31 113.7(5) . . ? C32 O6 C11 117.9(3) . . ? C34 O8 C12 118.4(2) . . ? C2 C1 C10 126.7(3) . . ? C2 C1 H1 116.7 . . ? C10 C1 H1 116.7 . . ? C1 C2 C3 122.3(3) . . ? C1 C2 H2 118.9 . . ? C3 C2 H2 118.9 . . ? O1 C3 C2 120.2(4) . . ? O1 C3 C4 119.7(4) . . ? C2 C3 C4 120.0(3) . . ? C3 C4 C28 108.8(3) . . ? C3 C4 C29 104.5(3) . . ? C28 C4 C29 108.6(4) . . ? C3 C4 C5 112.2(3) . . ? C28 C4 C5 108.1(3) . . ? C29 C4 C5 114.5(3) . . ? C6 C5 C4 109.8(3) . . ? C6 C5 C10 112.9(3) . . ? C4 C5 C10 115.8(3) . . ? C6 C5 H5 105.8 . . ? C4 C5 H5 105.8 . . ? C10 C5 H5 105.8 . . ? C7 C6 C5 116.9(3) . . ? C7 C6 H6A 108.1 . . ? C5 C6 H6A 108.1 . . ? C7 C6 H6B 108.1 . . ? C5 C6 H6B 108.1 . . ? H6A C6 H6B 107.3 . . ? O4 C7 O5 124.2(5) . . ? O4 C7 C6 123.6(6) . . ? O5 C7 C6 112.2(4) . . ? C14 C8 C30 121.6(3) . . ? C14 C8 C9 121.5(3) . . ? C30 C8 C9 116.6(3) . . ? C8 C9 C11 107.1(2) . . ? C8 C9 C10 113.6(2) . . ? C11 C9 C10 117.5(2) . . ? C8 C9 H9 105.9 . . ? C11 C9 H9 105.9 . . ? C10 C9 H9 105.9 . . ? C1 C10 C19 104.3(3) . . ? C1 C10 C5 111.8(3) . . ? C19 C10 C5 111.2(2) . . ? C1 C10 C9 108.9(2) . . ? C19 C10 C9 110.1(3) . . ? C5 C10 C9 110.5(2) . . ? O6 C11 C12 107.4(2) . . ? O6 C11 C9 112.8(2) . . ? C12 C11 C9 114.3(2) . . ? O6 C11 H11 107.4 . . ? C12 C11 H11 107.4 . . ? C9 C11 H11 107.4 . . ? O8 C12 C11 107.4(2) . . ? O8 C12 C13 109.05(19) . . ? C11 C12 C13 110.4(2) . . ? O8 C12 H12 110.0 . . ? C11 C12 H12 110.0 . . ? C13 C12 H12 110.0 . . ? C12 C13 C14 110.9(2) . . ? C12 C13 C18 111.4(2) . . ? C14 C13 C18 107.0(2) . . ? C12 C13 C17 115.9(2) . . ? C14 C13 C17 100.5(3) . . ? C18 C13 C17 110.4(2) . . ? C8 C14 C13 126.5(3) . . ? C8 C14 C15 126.2(3) . . ? C13 C14 C15 107.3(3) . . ? O2 C15 C14 114.4(3) . . ? O2 C15 C16 113.4(3) . . ? C14 C15 C16 104.6(3) . . ? O2 C15 H15 108.1 . . ? C14 C15 H15 108.1 . . ? C16 C15 H15 108.1 . . ? C15 C16 C17 106.8(3) . . ? C15 C16 H16A 110.4 . . ? C17 C16 H16A 110.4 . . ? C15 C16 H16B 110.4 . . ? C17 C16 H16B 110.4 . . ? H16A C16 H16B 108.6 . . ? C20 C17 C16 115.8(3) . . ? C20 C17 C13 116.2(3) . . ? C16 C17 C13 102.6(3) . . ? C20 C17 H17 107.2 . . ? C16 C17 H17 107.2 . . ? C13 C17 H17 107.2 . . ? C13 C18 H18A 109.5 . . ? C13 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C13 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C10 C19 H19A 109.5 . . ? C10 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C10 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C21 C20 C22 104.5(5) . . ? C21 C20 C17 129.7(4) . . ? C22 C20 C17 125.8(4) . . ? C20 C21 O3 112.6(5) . . ? C20 C21 H21 123.7 . . ? O3 C21 H21 123.7 . . ? C23 C22 C20 110.2(6) . . ? C23 C22 H22 124.9 . . ? C20 C22 H22 124.9 . . ? C22 C23 O3 108.8(5) . . ? C22 C23 H23 125.6 . . ? O3 C23 H23 125.6 . . ? C4 C28 H28A 109.5 . . ? C4 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C4 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C4 C29 H29A 109.5 . . ? C4 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C4 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C8 C30 Cl1 108.9(3) . . ? C8 C30 H30A 109.9 . . ? Cl1 C30 H30A 109.9 . . ? C8 C30 H30B 109.9 . . ? Cl1 C30 H30B 109.9 . . ? H30A C30 H30B 108.3 . . ? O5 C31 H31A 109.5 . . ? O5 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? O5 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? O7 C32 O6 123.6(4) . . ? O7 C32 C33 124.9(4) . . ? O6 C32 C33 111.4(4) . . ? C32 C33 H33A 109.5 . . ? C32 C33 H33B 109.5 . . ? H33A C33 H33B 109.5 . . ? C32 C33 H33C 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? O9 C34 O8 123.7(3) . . ? O9 C34 C35 126.0(4) . . ? O8 C34 C35 110.3(3) . . ? C34 C35 H35A 109.5 . . ? C34 C35 H35B 109.5 . . ? H35A C35 H35B 109.5 . . ? C34 C35 H35C 109.5 . . ? H35A C35 H35C 109.5 . . ? H35B C35 H35C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C10 C1 C2 C3 3.9(5) . . . . ? C1 C2 C3 O1 179.9(4) . . . . ? C1 C2 C3 C4 4.4(5) . . . . ? O1 C3 C4 C28 39.3(5) . . . . ? C2 C3 C4 C28 -145.1(4) . . . . ? O1 C3 C4 C29 -76.5(4) . . . . ? C2 C3 C4 C29 99.0(4) . . . . ? O1 C3 C4 C5 158.9(3) . . . . ? C2 C3 C4 C5 -25.6(4) . . . . ? C3 C4 C5 C6 168.5(3) . . . . ? C28 C4 C5 C6 -71.6(4) . . . . ? C29 C4 C5 C6 49.6(4) . . . . ? C3 C4 C5 C10 39.2(4) . . . . ? C28 C4 C5 C10 159.1(3) . . . . ? C29 C4 C5 C10 -79.7(4) . . . . ? C4 C5 C6 C7 162.2(4) . . . . ? C10 C5 C6 C7 -66.9(5) . . . . ? C31 O5 C7 O4 -2.3(6) . . . . ? C31 O5 C7 C6 179.2(3) . . . . ? C5 C6 C7 O4 123.9(5) . . . . ? C5 C6 C7 O5 -57.6(5) . . . . ? C14 C8 C9 C11 26.9(4) . . . . ? C30 C8 C9 C11 -147.1(3) . . . . ? C14 C8 C9 C10 -104.5(3) . . . . ? C30 C8 C9 C10 81.5(4) . . . . ? C2 C1 C10 C19 -109.9(4) . . . . ? C2 C1 C10 C5 10.4(4) . . . . ? C2 C1 C10 C9 132.7(3) . . . . ? C6 C5 C10 C1 -159.7(3) . . . . ? C4 C5 C10 C1 -31.9(4) . . . . ? C6 C5 C10 C19 -43.6(4) . . . . ? C4 C5 C10 C19 84.2(3) . . . . ? C6 C5 C10 C9 79.0(3) . . . . ? C4 C5 C10 C9 -153.2(3) . . . . ? C8 C9 C10 C1 73.4(3) . . . . ? C11 C9 C10 C1 -52.7(3) . . . . ? C8 C9 C10 C19 -40.3(4) . . . . ? C11 C9 C10 C19 -166.4(3) . . . . ? C8 C9 C10 C5 -163.5(2) . . . . ? C11 C9 C10 C5 70.4(3) . . . . ? C32 O6 C11 C12 115.4(3) . . . . ? C32 O6 C11 C9 -117.9(3) . . . . ? C8 C9 C11 O6 -175.0(2) . . . . ? C10 C9 C11 O6 -45.8(3) . . . . ? C8 C9 C11 C12 -52.0(3) . . . . ? C10 C9 C11 C12 77.2(3) . . . . ? C34 O8 C12 C11 106.5(3) . . . . ? C34 O8 C12 C13 -133.7(3) . . . . ? O6 C11 C12 O8 -53.4(2) . . . . ? C9 C11 C12 O8 -179.3(2) . . . . ? O6 C11 C12 C13 -172.3(2) . . . . ? C9 C11 C12 C13 61.9(3) . . . . ? O8 C12 C13 C14 -158.6(2) . . . . ? C11 C12 C13 C14 -40.8(3) . . . . ? O8 C12 C13 C18 -39.6(3) . . . . ? C11 C12 C13 C18 78.2(3) . . . . ? O8 C12 C13 C17 87.6(3) . . . . ? C11 C12 C13 C17 -154.5(3) . . . . ? C30 C8 C14 C13 161.3(3) . . . . ? C9 C8 C14 C13 -12.3(5) . . . . ? C30 C8 C14 C15 -18.4(5) . . . . ? C9 C8 C14 C15 167.9(3) . . . . ? C12 C13 C14 C8 18.6(4) . . . . ? C18 C13 C14 C8 -103.1(3) . . . . ? C17 C13 C14 C8 141.7(3) . . . . ? C12 C13 C14 C15 -161.6(2) . . . . ? C18 C13 C14 C15 76.7(3) . . . . ? C17 C13 C14 C15 -38.5(3) . . . . ? C8 C14 C15 O2 -35.5(5) . . . . ? C13 C14 C15 O2 144.7(3) . . . . ? C8 C14 C15 C16 -160.1(3) . . . . ? C13 C14 C15 C16 20.1(3) . . . . ? O2 C15 C16 C17 -118.1(3) . . . . ? C14 C15 C16 C17 7.1(3) . . . . ? C15 C16 C17 C20 -158.2(3) . . . . ? C15 C16 C17 C13 -30.6(3) . . . . ? C12 C13 C17 C20 -71.5(3) . . . . ? C14 C13 C17 C20 168.9(3) . . . . ? C18 C13 C17 C20 56.2(4) . . . . ? C12 C13 C17 C16 161.1(2) . . . . ? C14 C13 C17 C16 41.5(3) . . . . ? C18 C13 C17 C16 -71.1(3) . . . . ? C16 C17 C20 C21 34.9(6) . . . . ? C13 C17 C20 C21 -85.6(6) . . . . ? C16 C17 C20 C22 -147.0(5) . . . . ? C13 C17 C20 C22 92.5(6) . . . . ? C22 C20 C21 O3 0.5(7) . . . . ? C17 C20 C21 O3 179.0(4) . . . . ? C23 O3 C21 C20 0.6(7) . . . . ? C21 C20 C22 C23 -1.6(9) . . . . ? C17 C20 C22 C23 179.9(6) . . . . ? C20 C22 C23 O3 2.0(9) . . . . ? C21 O3 C23 C22 -1.6(8) . . . . ? C14 C8 C30 Cl1 -82.9(4) . . . . ? C9 C8 C30 Cl1 91.1(3) . . . . ? C11 O6 C32 O7 3.5(5) . . . . ? C11 O6 C32 C33 -178.1(3) . . . . ? C12 O8 C34 O9 1.8(5) . . . . ? C12 O8 C34 C35 -178.5(4) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O2 H3 O1 0.95(5) 1.89(5) 2.840(5) 177(5) 2_556 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.49 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.657 _refine_diff_density_min -0.542 _refine_diff_density_rms 0.046