# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2006 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 #============================================================================ # 1. SUBMISSION DETAILS _publ_contact_author ; Dr. J. F. Malone School of Chemistry and Chemical Engineering The Queen's University of Belfast Belfast UK BT9 5AG ; _publ_contact_author_phone '0044 2890 274349' _publ_contact_author_fax '0044 2890 974687' _publ_contact_author_email DR.BOYD@QUB.AC.UK _publ_requested_coeditor_name ? #============================================================================ # 2. TITLE AND AUTHOR LIST _publ_section_title ; Dioxygenase-catalysed dihydroxylation of arene cis-dihydrodiols and acetonide derivatives: a new approach to the synthesis of enantiopure tetraoxygenated arene bioproducts ; loop_ _publ_author_name _publ_author_address D.R.Boyd ; School of Chemistry and Chemical Engineering The Queen's University of Belfast Belfast UK BT9 5AG ; N.D.Sharma ; School of Chemistry and Chemical Engineering The Queen's University of Belfast Belfast UK BT9 5AG ; T.Belhocine ; School of Chemistry and Chemical Engineering The Queen's University of Belfast Belfast UK BT9 5AG ; J.F.Malone ; School of Chemistry and Chemical Engineering The Queen's University of Belfast Belfast UK BT9 5AG ; S.McGregor ; School of Chemistry and Chemical Engineering The Queen's University of Belfast Belfast UK BT9 5AG ; ; C.C.R.Allen ; ; QUESTOR Centre The Queen's University of Belfast Belfast UK BT9 5AG ; _publ_contact_author_name 'Prof. D.Boyd' #============================================================================ data_22bcam _database_code_depnum_ccdc_archive 'CCDC 618516' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C35 H39 Cl3 O8' _chemical_formula_weight 694.01 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 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 11.634(2) _cell_length_b 12.065(2) _cell_length_c 50.230(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 7050(2) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 985 _cell_measurement_theta_min 2.64 _cell_measurement_theta_max 22.62 _exptl_crystal_description blocks _exptl_crystal_colour colourless _exptl_crystal_size_max .60 _exptl_crystal_size_mid .40 _exptl_crystal_size_min .25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.308 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2912 _exptl_absorpt_coefficient_mu 0.309 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.8635 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'Bruker 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 'Bruker SMART CCD area detector' _diffrn_measurement_method 'phi and omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 58452 _diffrn_reflns_av_R_equivalents 0.0562 _diffrn_reflns_av_sigmaI/netI 0.0521 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -55 _diffrn_reflns_limit_l_max 55 _diffrn_reflns_theta_min 0.81 _diffrn_reflns_theta_max 23.31 _reflns_number_total 10148 _reflns_number_gt 6591 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _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 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.1272P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0021(4) _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 0.01(10) _refine_ls_number_reflns 10148 _refine_ls_number_parameters 842 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0995 _refine_ls_R_factor_gt 0.0664 _refine_ls_wR_factor_ref 0.1982 _refine_ls_wR_factor_gt 0.1770 _refine_ls_goodness_of_fit_ref 0.987 _refine_ls_restrained_S_all 0.987 _refine_ls_shift/su_max 0.041 _refine_ls_shift/su_mean 0.005 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 0.0021(4) 0.7462(4) 0.18604(9) 0.0478(12) Uani 1 1 d . . . H1 H -0.0270 0.6701 0.1870 0.057 Uiso 1 1 calc R . . C2 C 0.0958(4) 0.7555(5) 0.16509(11) 0.0556(14) Uani 1 1 d . . . H2 H 0.0649 0.7326 0.1478 0.067 Uiso 1 1 calc R . . C3 C 0.1366(5) 0.8723(5) 0.16331(11) 0.0604(15) Uani 1 1 d . . . H3A H 0.2038 0.8766 0.1519 0.073 Uiso 1 1 calc R . . H3B H 0.1573 0.8993 0.1808 0.073 Uiso 1 1 calc R . . C4 C 0.0398(5) 0.9422(5) 0.15180(11) 0.0579(14) Uani 1 1 d . . . H4A H 0.0565 1.0198 0.1549 0.069 Uiso 1 1 calc R . . H4B H 0.0366 0.9307 0.1327 0.069 Uiso 1 1 calc R . . C4A C -0.0764(4) 0.9151(4) 0.16365(10) 0.0490(13) Uani 1 1 d . . . C4B C -0.1750(4) 0.9820(4) 0.15655(10) 0.0500(13) Uani 1 1 d . . . C5 C -0.1670(6) 1.0724(5) 0.13846(11) 0.0633(16) Uani 1 1 d . . . H5 H -0.0964 1.0900 0.1309 0.076 Uiso 1 1 calc R . . C6 C -0.2599(7) 1.1324(5) 0.13221(12) 0.0764(19) Uani 1 1 d . . . H6 H -0.2526 1.1917 0.1205 0.092 Uiso 1 1 calc R . . C7 C -0.3685(7) 1.1077(6) 0.14303(14) 0.080(2) Uani 1 1 d . . . H7 H -0.4325 1.1495 0.1383 0.096 Uiso 1 1 calc R . . C8 C -0.3786(6) 1.0225(5) 0.16035(13) 0.0733(17) Uani 1 1 d . . . H8 H -0.4498 1.0074 0.1679 0.088 Uiso 1 1 calc R . . C8A C -0.2845(5) 0.9569(5) 0.16707(10) 0.0568(14) Uani 1 1 d . . . C9 C -0.2954(5) 0.8644(5) 0.18468(11) 0.0640(15) Uani 1 1 d . . . H9 H -0.3664 0.8479 0.1922 0.077 Uiso 1 1 calc R . . C10 C -0.2035(5) 0.8012(5) 0.19041(11) 0.0616(15) Uani 1 1 d . . . H10 H -0.2126 0.7403 0.2016 0.074 Uiso 1 1 calc R . . C10A C -0.0932(4) 0.8250(4) 0.17989(10) 0.0504(13) Uani 1 1 d . . . O1 O 0.0504(3) 0.7806(3) 0.21208(6) 0.0550(9) Uani 1 1 d . . . C11 C 0.0871(5) 0.7014(5) 0.22817(11) 0.0586(14) Uani 1 1 d . . . O11 O 0.0842(4) 0.6038(4) 0.22400(8) 0.0763(12) Uani 1 1 d . . . C12 C 0.1308(5) 0.7477(5) 0.25392(10) 0.0565(14) Uani 1 1 d . . . O12 O 0.1617(3) 0.8647(3) 0.25167(7) 0.0681(11) Uani 1 1 d . . . C13 C 0.2370(6) 0.6904(6) 0.26624(12) 0.0802(19) Uani 1 1 d . . . H13A H 0.2284 0.6105 0.2664 0.096 Uiso 1 1 calc R . . H13B H 0.3068 0.7098 0.2568 0.096 Uiso 1 1 calc R . . C14 C 0.2373(6) 0.7375(6) 0.29447(12) 0.083(2) Uani 1 1 d . . . H14A H 0.3062 0.7807 0.2977 0.100 Uiso 1 1 calc R . . H14B H 0.2324 0.6787 0.3076 0.100 Uiso 1 1 calc R . . C15 C 0.1293(5) 0.8113(5) 0.29516(11) 0.0689(16) Uani 1 1 d . . . C16 C 0.0940(7) 0.8508(7) 0.32311(12) 0.095(2) Uani 1 1 d . . . H16A H 0.1523 0.8989 0.3301 0.142 Uiso 1 1 calc R . . H16B H 0.0852 0.7878 0.3346 0.142 Uiso 1 1 calc R . . H16C H 0.0224 0.8902 0.3220 0.142 Uiso 1 1 calc R . . C17 C 0.0431(5) 0.7508(5) 0.27747(10) 0.0561(14) Uani 1 1 d . . . C18 C 0.0070(6) 0.6350(5) 0.28766(13) 0.0844(19) Uani 1 1 d . . . H18A H -0.0353 0.6427 0.3040 0.127 Uiso 1 1 calc R . . H18B H 0.0743 0.5908 0.2908 0.127 Uiso 1 1 calc R . . H18C H -0.0405 0.5994 0.2746 0.127 Uiso 1 1 calc R . . C19 C -0.0650(5) 0.8166(6) 0.27072(13) 0.0794(18) Uani 1 1 d . . . H19A H -0.1110 0.8254 0.2865 0.119 Uiso 1 1 calc R . . H19B H -0.1085 0.7776 0.2574 0.119 Uiso 1 1 calc R . . H19C H -0.0437 0.8882 0.2640 0.119 Uiso 1 1 calc R . . C20 C 0.1635(5) 0.9059(6) 0.27649(12) 0.0709(17) Uani 1 1 d . . . O20 O 0.1923(5) 1.0002(4) 0.28094(10) 0.0993(15) Uani 1 1 d . . . O2 O 0.1927(3) 0.6827(3) 0.17227(7) 0.0569(9) Uani 1 1 d . . . C21 C 0.1822(5) 0.5756(5) 0.16439(11) 0.0569(14) Uani 1 1 d . . . O21 O 0.1002(4) 0.5407(4) 0.15292(9) 0.0761(12) Uani 1 1 d . . . C22 C 0.2908(4) 0.5134(4) 0.17047(10) 0.0522(13) Uani 1 1 d . . . O22 O 0.2715(3) 0.3988(3) 0.16224(7) 0.0612(10) Uani 1 1 d . . . C23 C 0.3377(5) 0.5099(5) 0.19893(11) 0.0695(17) Uani 1 1 d . . . H23A H 0.2906 0.4638 0.2104 0.083 Uiso 1 1 calc R . . H23B H 0.3436 0.5836 0.2065 0.083 Uiso 1 1 calc R . . C24 C 0.4576(5) 0.4581(6) 0.19417(12) 0.0742(17) Uani 1 1 d . . . H24A H 0.4640 0.3870 0.2031 0.089 Uiso 1 1 calc R . . H24B H 0.5179 0.5066 0.2006 0.089 Uiso 1 1 calc R . . C25 C 0.4650(5) 0.4439(5) 0.16327(12) 0.0617(15) Uani 1 1 d . . . C26 C 0.5848(5) 0.4221(6) 0.15285(14) 0.085(2) Uani 1 1 d . . . H26A H 0.6122 0.3527 0.1597 0.127 Uiso 1 1 calc R . . H26B H 0.6352 0.4806 0.1585 0.127 Uiso 1 1 calc R . . H26C H 0.5831 0.4191 0.1338 0.127 Uiso 1 1 calc R . . C27 C 0.3970(4) 0.5467(5) 0.15311(11) 0.0561(14) Uani 1 1 d . . . C28 C 0.4527(5) 0.6566(5) 0.16011(14) 0.0769(18) Uani 1 1 d . . . H28A H 0.5270 0.6611 0.1519 0.115 Uiso 1 1 calc R . . H28B H 0.4611 0.6621 0.1791 0.115 Uiso 1 1 calc R . . H28C H 0.4053 0.7163 0.1538 0.115 Uiso 1 1 calc R . . C29 C 0.3720(6) 0.5418(6) 0.12320(11) 0.0738(17) Uani 1 1 d . . . H29A H 0.3098 0.5912 0.1190 0.111 Uiso 1 1 calc R . . H29B H 0.3512 0.4675 0.1183 0.111 Uiso 1 1 calc R . . H29C H 0.4394 0.5637 0.1135 0.111 Uiso 1 1 calc R . . C30 C 0.3772(5) 0.3558(5) 0.15759(11) 0.0632(16) Uani 1 1 d . . . O30 O 0.3873(4) 0.2613(4) 0.15069(9) 0.0792(12) Uani 1 1 d . . . C31 C 0.2966(9) 0.5955(8) 0.02197(15) 0.118(3) Uani 1 1 d . . . H31 H 0.2821 0.5276 0.0118 0.142 Uiso 1 1 calc R . . Cl1 Cl 0.4245(4) 0.6538(4) 0.01026(8) 0.221(2) Uani 1 1 d . . . Cl2 Cl 0.3109(4) 0.5604(2) 0.05429(5) 0.1665(13) Uani 1 1 d . . . Cl3 Cl 0.1819(4) 0.6862(3) 0.01640(5) 0.1876(15) Uani 1 1 d . . . C1' C -0.0420(5) 1.2560(4) 0.06769(9) 0.0516(13) Uani 1 1 d . . . H1' H -0.1233 1.2353 0.0665 0.062 Uiso 1 1 calc R . . C2' C -0.0239(5) 1.3418(4) 0.08955(10) 0.0550(14) Uani 1 1 d . . . H2' H -0.0597 1.3153 0.1060 0.066 Uiso 1 1 calc R . . C3' C 0.1016(5) 1.3632(4) 0.09462(11) 0.0588(14) Uani 1 1 d . . . H3'1 H 0.1100 1.4214 0.1078 0.071 Uiso 1 1 calc R . . H3'2 H 0.1384 1.3875 0.0783 0.071 Uiso 1 1 calc R . . C4' C 0.1582(5) 1.2582(5) 0.10453(11) 0.0643(15) Uani 1 1 d . . . H4'1 H 0.2410 1.2674 0.1036 0.077 Uiso 1 1 calc R . . H4'2 H 0.1378 1.2474 0.1231 0.077 Uiso 1 1 calc R . . C4A' C 0.1256(5) 1.1558(4) 0.08916(10) 0.0517(13) Uani 1 1 d . . . C4B' C 0.1919(4) 1.0573(4) 0.09258(10) 0.0533(13) Uani 1 1 d . . . C5' C 0.2876(5) 1.0522(5) 0.10974(11) 0.0620(15) Uani 1 1 d . . . H5' H 0.3075 1.1138 0.1199 0.074 Uiso 1 1 calc R . . C6' C 0.3518(5) 0.9567(6) 0.11156(13) 0.0738(18) Uani 1 1 d . . . H6' H 0.4160 0.9551 0.1226 0.089 Uiso 1 1 calc R . . C7' C 0.3223(6) 0.8632(6) 0.09729(14) 0.0760(18) Uani 1 1 d . . . H7' H 0.3669 0.7995 0.0988 0.091 Uiso 1 1 calc R . . C8' C 0.2300(6) 0.8633(5) 0.08123(12) 0.0706(17) Uani 1 1 d . . . H8' H 0.2106 0.7988 0.0721 0.085 Uiso 1 1 calc R . . C8A' C 0.1604(4) 0.9610(4) 0.07775(11) 0.0534(14) Uani 1 1 d . . . C9' C 0.0651(5) 0.9638(5) 0.06076(12) 0.0657(16) Uani 1 1 d . . . H9' H 0.0450 0.9010 0.0511 0.079 Uiso 1 1 calc R . . C10' C 0.0021(5) 1.0577(5) 0.05833(11) 0.0622(15) Uani 1 1 d . . . H10' H -0.0616 1.0581 0.0471 0.075 Uiso 1 1 calc R . . C10" C 0.0312(4) 1.1553(4) 0.07249(10) 0.0473(12) Uani 1 1 d . . . O1' O -0.0018(3) 1.3028(3) 0.04235(6) 0.0539(9) Uani 1 1 d . . . C11' C -0.0822(5) 1.3432(4) 0.02546(10) 0.0511(13) Uani 1 1 d . . . O11' O -0.1838(3) 1.3461(3) 0.03020(7) 0.0680(11) Uani 1 1 d . . . C12' C -0.0333(4) 1.3785(4) -0.00061(10) 0.0510(13) Uani 1 1 d . . . O12' O 0.0896(3) 1.4027(3) 0.00206(7) 0.0592(10) Uani 1 1 d . . . C13' C -0.0851(5) 1.4818(5) -0.01292(11) 0.0660(16) Uani 1 1 d . . . H13C H -0.0601 1.5480 -0.0036 0.079 Uiso 1 1 calc R . . H13D H -0.1684 1.4787 -0.0127 0.079 Uiso 1 1 calc R . . C14' C -0.0384(6) 1.4794(6) -0.04153(12) 0.083(2) Uani 1 1 d . . . H14C H 0.0086 1.5440 -0.0452 0.100 Uiso 1 1 calc R . . H14D H -0.1003 1.4755 -0.0544 0.100 Uiso 1 1 calc R . . C15' C 0.0363(5) 1.3693(5) -0.04171(10) 0.0596(14) Uani 1 1 d . . . C16' C 0.0740(7) 1.3274(7) -0.06882(12) 0.091(2) Uani 1 1 d . . . H16D H 0.1241 1.3808 -0.0769 0.137 Uiso 1 1 calc R . . H16E H 0.0077 1.3167 -0.0799 0.137 Uiso 1 1 calc R . . H16F H 0.1139 1.2583 -0.0668 0.137 Uiso 1 1 calc R . . C17' C -0.0340(4) 1.2919(4) -0.02339(10) 0.0540(13) Uani 1 1 d . . . C18' C -0.1557(5) 1.2627(6) -0.03322(13) 0.0796(19) Uani 1 1 d . . . H18D H -0.1507 1.2259 -0.0501 0.119 Uiso 1 1 calc R . . H18E H -0.2001 1.3293 -0.0351 0.119 Uiso 1 1 calc R . . H18F H -0.1923 1.2146 -0.0206 0.119 Uiso 1 1 calc R . . C19' C 0.0261(6) 1.1837(5) -0.01641(12) 0.0738(17) Uani 1 1 d . . . H19D H 0.0244 1.1350 -0.0315 0.111 Uiso 1 1 calc R . . H19E H -0.0127 1.1492 -0.0017 0.111 Uiso 1 1 calc R . . H19F H 0.1044 1.1986 -0.0116 0.111 Uiso 1 1 calc R . . C20' C 0.1331(5) 1.3998(5) -0.02311(11) 0.0619(15) Uani 1 1 d . . . O20' O 0.2321(4) 1.4212(4) -0.02730(9) 0.0872(13) Uani 1 1 d . . . O2' O -0.0778(3) 1.4452(3) 0.08170(7) 0.0628(10) Uani 1 1 d . . . C21' C -0.1892(5) 1.4583(5) 0.08727(11) 0.0571(14) Uani 1 1 d . . . O21' O -0.2479(4) 1.3900(4) 0.09716(10) 0.0831(13) Uani 1 1 d . . . C22' C -0.2247(5) 1.5729(5) 0.07934(11) 0.0568(14) Uani 1 1 d . . . O22' O -0.3447(4) 1.5834(4) 0.08353(12) 0.1030(17) Uani 1 1 d . . . C23' C -0.2022(9) 1.6093(6) 0.04969(13) 0.113(3) Uani 1 1 d . . . H23C H -0.1234 1.5952 0.0444 0.136 Uiso 1 1 calc R . . H23D H -0.2540 1.5723 0.0374 0.136 Uiso 1 1 calc R . . C24' C -0.2272(9) 1.7330(6) 0.05138(13) 0.106(3) Uani 1 1 d . . . H24C H -0.2914 1.7528 0.0400 0.128 Uiso 1 1 calc R . . H24D H -0.1605 1.7760 0.0461 0.128 Uiso 1 1 calc R . . C25' C -0.2564(5) 1.7532(5) 0.08082(11) 0.0598(14) Uani 1 1 d . . . C26' C -0.2545(8) 1.8741(5) 0.08910(18) 0.109(3) Uani 1 1 d . . . H26D H -0.2944 1.9177 0.0761 0.164 Uiso 1 1 calc R . . H26E H -0.1763 1.8989 0.0904 0.164 Uiso 1 1 calc R . . H26F H -0.2916 1.8821 0.1061 0.164 Uiso 1 1 calc R . . C27' C -0.1719(5) 1.6696(5) 0.09374(13) 0.0704(17) Uani 1 1 d . . . C28' C -0.0487(7) 1.6927(6) 0.09143(18) 0.106(3) Uani 1 1 d . . . H28D H -0.0060 1.6365 0.1007 0.159 Uiso 1 1 calc R . . H28E H -0.0322 1.7638 0.0991 0.159 Uiso 1 1 calc R . . H28F H -0.0270 1.6930 0.0730 0.159 Uiso 1 1 calc R . . C29' C -0.1980(8) 1.6563(6) 0.12507(12) 0.105(3) Uani 1 1 d . . . H29D H -0.1612 1.5905 0.1316 0.157 Uiso 1 1 calc R . . H29E H -0.2794 1.6508 0.1278 0.157 Uiso 1 1 calc R . . H29F H -0.1689 1.7197 0.1344 0.157 Uiso 1 1 calc R . . C30' C -0.3624(7) 1.6968(7) 0.08634(19) 0.108(3) Uani 1 1 d . . . O30' O -0.4571(6) 1.7297(6) 0.0899(2) 0.187(4) Uani 1 1 d . . . C31' C 0.3683(9) 0.0748(7) 0.23394(18) 0.124(3) Uani 1 1 d . . . H31' H 0.2978 0.0457 0.2420 0.149 Uiso 1 1 calc R . . Cl1' Cl 0.4692(4) -0.0256(3) 0.23519(6) 0.1904(16) Uani 1 1 d . . . Cl2' Cl 0.3361(3) 0.1149(3) 0.20149(5) 0.1442(10) Uani 1 1 d . . . Cl3' Cl 0.4145(3) 0.1886(3) 0.25306(7) 0.1725(12) 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 0.052(3) 0.045(3) 0.046(3) 0.003(2) 0.002(2) 0.005(3) C2 0.049(3) 0.058(4) 0.059(3) -0.008(3) -0.003(3) 0.019(3) C3 0.057(3) 0.061(4) 0.064(3) 0.008(3) 0.010(3) 0.012(3) C4 0.064(3) 0.047(3) 0.062(3) 0.003(3) 0.005(3) 0.000(3) C4A 0.057(3) 0.050(3) 0.041(3) -0.001(2) 0.006(2) 0.006(3) C4B 0.055(3) 0.046(3) 0.049(3) -0.002(2) -0.003(3) 0.009(3) C5 0.079(4) 0.047(3) 0.064(4) -0.005(3) -0.015(3) 0.011(3) C6 0.111(6) 0.054(4) 0.064(4) -0.005(3) -0.030(4) 0.019(4) C7 0.087(5) 0.062(4) 0.091(5) -0.011(4) -0.029(4) 0.025(4) C8 0.075(4) 0.066(4) 0.079(4) -0.005(4) -0.012(3) 0.013(3) C8A 0.056(3) 0.066(4) 0.048(3) -0.007(3) -0.009(3) 0.012(3) C9 0.052(3) 0.079(4) 0.062(4) 0.007(3) 0.009(3) 0.007(3) C10 0.066(4) 0.063(4) 0.056(3) 0.008(3) 0.015(3) 0.007(3) C10A 0.053(3) 0.052(3) 0.046(3) 0.000(3) -0.002(2) 0.006(3) O1 0.065(2) 0.056(2) 0.0437(19) 0.0028(17) -0.0013(17) 0.0067(18) C11 0.068(4) 0.053(4) 0.056(3) 0.006(3) -0.001(3) 0.006(3) O11 0.109(3) 0.052(3) 0.068(3) 0.007(2) -0.021(2) 0.005(2) C12 0.062(3) 0.053(3) 0.054(3) 0.006(3) 0.004(3) -0.002(3) O12 0.072(3) 0.078(3) 0.054(2) 0.007(2) 0.0053(19) -0.014(2) C13 0.070(4) 0.107(5) 0.064(4) 0.000(4) -0.018(3) 0.020(4) C14 0.078(4) 0.110(5) 0.062(4) -0.002(4) -0.020(3) 0.018(4) C15 0.079(4) 0.075(4) 0.053(3) 0.004(3) 0.002(3) 0.006(3) C16 0.116(6) 0.114(6) 0.055(4) -0.007(4) 0.009(4) 0.004(5) C17 0.061(3) 0.059(3) 0.048(3) 0.004(3) 0.004(3) 0.001(3) C18 0.103(5) 0.072(4) 0.078(4) 0.016(4) 0.012(4) -0.017(4) C19 0.060(4) 0.091(5) 0.087(4) -0.004(4) 0.008(3) 0.007(3) C20 0.074(4) 0.074(5) 0.064(4) -0.004(3) -0.003(3) -0.011(4) O20 0.119(4) 0.078(3) 0.101(4) -0.008(3) -0.003(3) -0.029(3) O2 0.055(2) 0.055(2) 0.061(2) -0.0055(18) -0.0020(17) 0.0134(18) C21 0.062(4) 0.052(4) 0.057(3) -0.005(3) 0.004(3) 0.017(3) O21 0.067(3) 0.075(3) 0.087(3) -0.016(2) -0.023(2) 0.011(2) C22 0.053(3) 0.050(3) 0.054(3) -0.001(2) 0.000(3) 0.006(3) O22 0.057(2) 0.051(2) 0.076(3) 0.0010(19) 0.0004(19) 0.0075(18) C23 0.070(4) 0.078(4) 0.060(4) -0.002(3) 0.005(3) 0.023(3) C24 0.068(4) 0.081(4) 0.074(4) 0.005(3) -0.018(3) 0.013(3) C25 0.058(3) 0.058(3) 0.070(4) -0.002(3) -0.005(3) 0.010(3) C26 0.061(4) 0.105(5) 0.088(5) 0.002(4) 0.007(3) 0.026(4) C27 0.046(3) 0.056(3) 0.066(3) 0.005(3) 0.003(3) 0.008(3) C28 0.067(4) 0.064(4) 0.099(5) -0.007(4) 0.003(3) -0.008(3) C29 0.075(4) 0.080(4) 0.067(4) 0.012(3) 0.007(3) 0.008(3) C30 0.076(4) 0.058(4) 0.056(3) 0.000(3) -0.009(3) 0.020(3) O30 0.094(3) 0.053(3) 0.091(3) -0.009(2) -0.015(2) 0.021(2) C31 0.154(8) 0.120(7) 0.081(5) -0.016(5) -0.002(5) 0.003(6) Cl1 0.200(4) 0.297(5) 0.167(3) 0.071(3) -0.012(3) -0.069(4) Cl2 0.295(4) 0.1145(18) 0.0899(15) 0.0184(13) 0.004(2) 0.007(2) Cl3 0.245(4) 0.210(3) 0.1076(19) -0.012(2) -0.005(2) 0.083(3) C1' 0.055(3) 0.061(3) 0.038(3) 0.009(3) 0.001(2) -0.007(3) C2' 0.062(3) 0.050(3) 0.053(3) 0.007(3) 0.001(3) 0.012(3) C3' 0.069(4) 0.045(3) 0.063(3) -0.009(3) -0.012(3) 0.008(3) C4' 0.073(4) 0.057(4) 0.062(3) -0.008(3) -0.012(3) 0.004(3) C4A' 0.054(3) 0.048(3) 0.053(3) 0.003(3) 0.004(3) 0.001(3) C4B' 0.056(3) 0.051(3) 0.053(3) 0.008(3) 0.008(3) 0.002(3) C5' 0.060(4) 0.065(4) 0.060(3) 0.015(3) 0.005(3) 0.007(3) C6' 0.061(4) 0.081(5) 0.079(4) 0.020(4) 0.004(3) 0.002(4) C7' 0.073(4) 0.061(4) 0.094(5) 0.010(4) 0.001(4) 0.017(4) C8' 0.082(4) 0.048(4) 0.082(4) 0.006(3) 0.009(4) 0.011(3) C8A' 0.056(3) 0.043(3) 0.061(3) 0.006(3) 0.009(3) 0.000(3) C9' 0.075(4) 0.050(4) 0.071(4) 0.002(3) -0.020(3) -0.004(3) C10' 0.068(4) 0.059(4) 0.060(3) 0.009(3) -0.009(3) -0.003(3) C10" 0.050(3) 0.045(3) 0.047(3) 0.005(2) 0.001(2) 0.006(2) O1' 0.048(2) 0.061(2) 0.053(2) 0.0117(18) 0.0022(17) 0.0029(17) C11' 0.051(3) 0.055(3) 0.047(3) 0.002(3) 0.001(3) 0.007(3) O11' 0.053(2) 0.091(3) 0.061(2) 0.008(2) -0.0010(19) 0.007(2) C12' 0.045(3) 0.055(3) 0.053(3) 0.000(3) -0.004(2) 0.001(3) O12' 0.054(2) 0.071(3) 0.053(2) 0.0018(18) -0.0009(18) -0.0127(19) C13' 0.076(4) 0.067(4) 0.055(3) 0.015(3) 0.005(3) 0.021(3) C14' 0.089(5) 0.110(6) 0.052(3) 0.019(3) 0.000(3) 0.019(4) C15' 0.060(3) 0.068(4) 0.051(3) -0.002(3) 0.010(3) 0.001(3) C16' 0.106(5) 0.115(6) 0.053(4) -0.009(4) 0.021(4) -0.005(5) C17' 0.051(3) 0.060(3) 0.051(3) -0.003(3) 0.003(3) -0.002(3) C18' 0.060(4) 0.105(5) 0.073(4) -0.007(4) -0.011(3) -0.018(4) C19' 0.081(4) 0.067(4) 0.074(4) -0.008(3) 0.012(3) 0.004(3) C20' 0.063(4) 0.064(4) 0.059(4) 0.008(3) 0.004(3) 0.003(3) O20' 0.066(3) 0.106(4) 0.090(3) 0.005(3) 0.016(2) -0.014(3) O2' 0.065(3) 0.054(2) 0.069(2) 0.0034(19) 0.001(2) 0.009(2) C21' 0.065(4) 0.048(3) 0.059(3) -0.001(3) 0.005(3) 0.006(3) O21' 0.073(3) 0.059(3) 0.117(4) 0.015(3) 0.024(3) 0.006(2) C22' 0.052(3) 0.054(4) 0.064(3) -0.004(3) -0.006(3) 0.010(3) O22' 0.059(3) 0.065(3) 0.185(5) 0.013(3) 0.002(3) 0.008(2) C23' 0.178(8) 0.099(6) 0.063(4) -0.001(4) -0.009(5) 0.054(6) C24' 0.162(8) 0.087(5) 0.070(4) 0.011(4) -0.012(5) 0.046(5) C25' 0.066(4) 0.049(3) 0.064(4) -0.001(3) 0.005(3) 0.010(3) C26' 0.130(7) 0.050(4) 0.149(7) -0.008(5) 0.000(5) 0.017(4) C27' 0.069(4) 0.049(3) 0.094(4) -0.002(3) 0.005(3) 0.010(3) C28' 0.100(6) 0.067(4) 0.151(7) 0.016(5) -0.039(5) -0.016(4) C29' 0.156(8) 0.090(5) 0.068(4) -0.017(4) -0.008(5) 0.016(5) C30' 0.081(5) 0.067(5) 0.176(9) 0.025(5) 0.036(5) 0.031(4) O30' 0.083(4) 0.135(6) 0.342(12) 0.050(7) 0.054(6) 0.042(4) C31' 0.156(8) 0.097(6) 0.121(7) 0.022(5) 0.062(6) 0.035(6) Cl1' 0.245(4) 0.207(3) 0.119(2) 0.017(2) 0.015(2) 0.118(3) Cl2' 0.141(2) 0.174(2) 0.1174(17) 0.0389(17) 0.0104(15) 0.0337(19) Cl3' 0.188(3) 0.151(3) 0.179(3) -0.027(2) 0.021(2) -0.024(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.483(6) . ? C1 C10A 1.492(7) . ? C1 C2 1.520(7) . ? C2 O2 1.474(6) . ? C2 C3 1.489(8) . ? C3 C4 1.521(7) . ? C4 C4A 1.513(7) . ? C4A C10A 1.373(7) . ? C4A C4B 1.447(7) . ? C4B C8A 1.412(8) . ? C4B C5 1.423(8) . ? C5 C6 1.338(8) . ? C6 C7 1.407(10) . ? C7 C8 1.352(9) . ? C8 C8A 1.393(8) . ? C8A C9 1.429(8) . ? C9 C10 1.344(8) . ? C10 C10A 1.418(8) . ? O1 C11 1.322(6) . ? C11 O11 1.197(6) . ? C11 C12 1.498(8) . ? C12 O12 1.461(7) . ? C12 C13 1.545(8) . ? C12 C17 1.563(7) . ? O12 C20 1.342(7) . ? C13 C14 1.528(9) . ? C14 C15 1.540(9) . ? C15 C17 1.525(9) . ? C15 C20 1.530(9) . ? C15 C16 1.538(9) . ? C17 C19 1.525(8) . ? C17 C18 1.547(8) . ? C20 O20 1.208(7) . ? O2 C21 1.356(7) . ? C21 O21 1.192(7) . ? C21 C22 1.501(8) . ? C22 O22 1.461(6) . ? C22 C23 1.530(8) . ? C22 C27 1.564(8) . ? O22 C30 1.355(7) . ? C23 C24 1.547(8) . ? C24 C25 1.564(8) . ? C25 C30 1.501(9) . ? C25 C26 1.512(8) . ? C25 C27 1.557(8) . ? C27 C28 1.518(8) . ? C27 C29 1.531(8) . ? C30 O30 1.198(7) . ? C31 Cl2 1.686(8) . ? C31 Cl1 1.747(10) . ? C31 Cl3 1.749(10) . ? C1' O1' 1.469(6) . ? C1' C10" 1.503(7) . ? C1' C2' 1.524(7) . ? C2' O2' 1.450(6) . ? C2' C3' 1.504(8) . ? C3' C4' 1.513(8) . ? C4' C4A' 1.505(8) . ? C4A' C10" 1.381(7) . ? C4A' C4B' 1.427(7) . ? C4B' C5' 1.409(8) . ? C4B' C8A' 1.428(8) . ? C5' C6' 1.376(8) . ? C6' C7' 1.380(9) . ? C7' C8' 1.343(9) . ? C8' C8A' 1.441(8) . ? C8A' C9' 1.399(8) . ? C9' C10' 1.355(8) . ? C10' C10" 1.417(8) . ? O1' C11' 1.354(6) . ? C11' O11' 1.206(6) . ? C11' C12' 1.490(7) . ? C12' O12' 1.465(6) . ? C12' C13' 1.516(8) . ? C12' C17' 1.550(7) . ? O12' C20' 1.363(7) . ? C13' C14' 1.537(8) . ? C14' C15' 1.587(9) . ? C15' C20' 1.509(8) . ? C15' C16' 1.517(8) . ? C15' C17' 1.545(8) . ? C17' C19' 1.522(8) . ? C17' C18' 1.541(8) . ? C20' O20' 1.199(7) . ? O2' C21' 1.336(7) . ? C21' O21' 1.180(6) . ? C21' C22' 1.497(8) . ? C22' O22' 1.418(7) . ? C22' C27' 1.504(8) . ? C22' C23' 1.575(9) . ? O22' C30' 1.390(9) . ? C23' C24' 1.523(10) . ? C24' C25' 1.537(9) . ? C25' C30' 1.435(10) . ? C25' C26' 1.517(8) . ? C25' C27' 1.551(8) . ? C27' C28' 1.465(10) . ? C27' C29' 1.611(9) . ? C30' O30' 1.185(9) . ? C31' Cl1' 1.689(9) . ? C31' Cl2' 1.740(10) . ? C31' Cl3' 1.759(10) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 C10A 106.6(4) . . ? O1 C1 C2 108.5(4) . . ? C10A C1 C2 110.0(4) . . ? O2 C2 C3 109.6(4) . . ? O2 C2 C1 109.6(4) . . ? C3 C2 C1 109.9(4) . . ? C2 C3 C4 108.2(5) . . ? C4A C4 C3 113.1(4) . . ? C10A C4A C4B 118.4(5) . . ? C10A C4A C4 122.1(5) . . ? C4B C4A C4 119.4(4) . . ? C8A C4B C5 117.6(5) . . ? C8A C4B C4A 120.2(5) . . ? C5 C4B C4A 122.2(5) . . ? C6 C5 C4B 120.8(6) . . ? C5 C6 C7 121.3(6) . . ? C8 C7 C6 119.2(6) . . ? C7 C8 C8A 121.3(7) . . ? C8 C8A C4B 119.8(6) . . ? C8 C8A C9 121.6(6) . . ? C4B C8A C9 118.7(5) . . ? C10 C9 C8A 120.3(5) . . ? C9 C10 C10A 121.7(5) . . ? C4A C10A C10 120.7(5) . . ? C4A C10A C1 121.5(5) . . ? C10 C10A C1 117.8(5) . . ? C11 O1 C1 117.3(4) . . ? O11 C11 O1 126.5(5) . . ? O11 C11 C12 121.9(5) . . ? O1 C11 C12 111.6(5) . . ? O12 C12 C11 112.2(4) . . ? O12 C12 C13 105.4(5) . . ? C11 C12 C13 116.7(5) . . ? O12 C12 C17 101.3(4) . . ? C11 C12 C17 116.2(5) . . ? C13 C12 C17 103.3(4) . . ? C20 O12 C12 106.8(4) . . ? C14 C13 C12 101.9(5) . . ? C13 C14 C15 103.5(5) . . ? C17 C15 C20 99.8(4) . . ? C17 C15 C16 120.3(5) . . ? C20 C15 C16 113.4(6) . . ? C17 C15 C14 104.3(5) . . ? C20 C15 C14 101.8(5) . . ? C16 C15 C14 114.7(5) . . ? C15 C17 C19 115.0(5) . . ? C15 C17 C18 114.7(5) . . ? C19 C17 C18 108.7(5) . . ? C15 C17 C12 91.3(4) . . ? C19 C17 C12 112.5(4) . . ? C18 C17 C12 114.0(5) . . ? O20 C20 O12 121.6(6) . . ? O20 C20 C15 131.5(6) . . ? O12 C20 C15 106.8(5) . . ? C21 O2 C2 115.3(4) . . ? O21 C21 O2 123.4(5) . . ? O21 C21 C22 126.6(5) . . ? O2 C21 C22 109.9(5) . . ? O22 C22 C21 106.6(4) . . ? O22 C22 C23 107.0(4) . . ? C21 C22 C23 120.3(4) . . ? O22 C22 C27 101.9(4) . . ? C21 C22 C27 115.0(4) . . ? C23 C22 C27 104.3(4) . . ? C30 O22 C22 105.8(4) . . ? C22 C23 C24 100.9(4) . . ? C23 C24 C25 104.3(4) . . ? C30 C25 C26 116.0(5) . . ? C30 C25 C27 98.9(4) . . ? C26 C25 C27 119.6(5) . . ? C30 C25 C24 103.2(5) . . ? C26 C25 C24 114.4(5) . . ? C27 C25 C24 102.1(4) . . ? C28 C27 C29 110.0(5) . . ? C28 C27 C25 113.7(5) . . ? C29 C27 C25 112.8(5) . . ? C28 C27 C22 115.6(5) . . ? C29 C27 C22 112.8(4) . . ? C25 C27 C22 90.8(4) . . ? O30 C30 O22 120.2(6) . . ? O30 C30 C25 131.4(6) . . ? O22 C30 C25 108.3(5) . . ? Cl2 C31 Cl1 110.0(6) . . ? Cl2 C31 Cl3 112.8(5) . . ? Cl1 C31 Cl3 110.1(5) . . ? O1' C1' C10" 105.6(4) . . ? O1' C1' C2' 108.6(4) . . ? C10" C1' C2' 110.8(4) . . ? O2' C2' C3' 108.5(4) . . ? O2' C2' C1' 109.2(4) . . ? C3' C2' C1' 111.9(4) . . ? C2' C3' C4' 109.6(5) . . ? C4A' C4' C3' 114.1(4) . . ? C10" C4A' C4B' 119.9(5) . . ? C10" C4A' C4' 121.0(5) . . ? C4B' C4A' C4' 119.0(5) . . ? C5' C4B' C4A' 122.5(5) . . ? C5' C4B' C8A' 119.1(5) . . ? C4A' C4B' C8A' 118.4(5) . . ? C6' C5' C4B' 120.4(6) . . ? C5' C6' C7' 121.0(6) . . ? C8' C7' C6' 120.6(6) . . ? C7' C8' C8A' 121.5(6) . . ? C9' C8A' C4B' 120.1(5) . . ? C9' C8A' C8' 122.6(5) . . ? C4B' C8A' C8' 117.3(5) . . ? C10' C9' C8A' 120.3(5) . . ? C9' C10' C10" 121.4(5) . . ? C4A' C10" C10' 119.9(5) . . ? C4A' C10" C1' 123.0(5) . . ? C10' C10" C1' 117.1(5) . . ? C11' O1' C1' 117.5(4) . . ? O11' C11' O1' 124.3(5) . . ? O11' C11' C12' 122.6(5) . . ? O1' C11' C12' 112.9(4) . . ? O12' C12' C11' 110.4(4) . . ? O12' C12' C13' 105.2(4) . . ? C11' C12' C13' 116.2(4) . . ? O12' C12' C17' 102.0(4) . . ? C11' C12' C17' 117.0(4) . . ? C13' C12' C17' 104.6(4) . . ? C20' O12' C12' 105.8(4) . . ? C12' C13' C14' 103.0(5) . . ? C13' C14' C15' 102.4(4) . . ? C20' C15' C16' 114.9(5) . . ? C20' C15' C17' 100.0(4) . . ? C16' C15' C17' 119.1(5) . . ? C20' C15' C14' 101.6(5) . . ? C16' C15' C14' 116.2(5) . . ? C17' C15' C14' 102.3(4) . . ? C19' C17' C18' 107.4(5) . . ? C19' C17' C15' 114.4(4) . . ? C18' C17' C15' 115.7(5) . . ? C19' C17' C12' 114.0(4) . . ? C18' C17' C12' 113.3(4) . . ? C15' C17' C12' 91.7(4) . . ? O20' C20' O12' 121.0(5) . . ? O20' C20' C15' 131.4(6) . . ? O12' C20' C15' 107.6(5) . . ? C21' O2' C2' 117.7(4) . . ? O21' C21' O2' 124.5(5) . . ? O21' C21' C22' 126.7(5) . . ? O2' C21' C22' 108.8(5) . . ? O22' C22' C21' 108.3(5) . . ? O22' C22' C27' 105.2(5) . . ? C21' C22' C27' 118.4(5) . . ? O22' C22' C23' 106.2(5) . . ? C21' C22' C23' 117.6(5) . . ? C27' C22' C23' 99.8(5) . . ? C30' O22' C22' 104.4(5) . . ? C24' C23' C22' 100.9(5) . . ? C23' C24' C25' 104.5(5) . . ? C30' C25' C26' 114.6(6) . . ? C30' C25' C24' 107.5(7) . . ? C26' C25' C24' 114.4(6) . . ? C30' C25' C27' 99.0(5) . . ? C26' C25' C27' 120.1(6) . . ? C24' C25' C27' 99.2(5) . . ? C28' C27' C22' 120.6(6) . . ? C28' C27' C25' 117.6(5) . . ? C22' C27' C25' 92.5(5) . . ? C28' C27' C29' 106.3(6) . . ? C22' C27' C29' 108.4(5) . . ? C25' C27' C29' 110.7(5) . . ? O30' C30' O22' 118.9(8) . . ? O30' C30' C25' 132.0(7) . . ? O22' C30' C25' 108.7(6) . . ? Cl1' C31' Cl2' 112.6(5) . . ? Cl1' C31' Cl3' 109.1(6) . . ? Cl2' C31' Cl3' 111.1(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 O1 C1 C2 O2 60.1(5) . . . . ? C10A C1 C2 O2 176.4(4) . . . . ? O1 C1 C2 C3 -60.4(5) . . . . ? C10A C1 C2 C3 55.9(6) . . . . ? O2 C2 C3 C4 171.4(4) . . . . ? C1 C2 C3 C4 -68.1(6) . . . . ? C2 C3 C4 C4A 43.4(6) . . . . ? C3 C4 C4A C10A -9.6(7) . . . . ? C3 C4 C4A C4B 174.1(5) . . . . ? C10A C4A C4B C8A 2.5(7) . . . . ? C4 C4A C4B C8A 179.0(5) . . . . ? C10A C4A C4B C5 -175.8(5) . . . . ? C4 C4A C4B C5 0.7(7) . . . . ? C8A C4B C5 C6 1.4(8) . . . . ? C4A C4B C5 C6 179.7(5) . . . . ? C4B C5 C6 C7 -0.7(9) . . . . ? C5 C6 C7 C8 0.9(9) . . . . ? C6 C7 C8 C8A -1.9(9) . . . . ? C7 C8 C8A C4B 2.7(9) . . . . ? C7 C8 C8A C9 -177.9(6) . . . . ? C5 C4B C8A C8 -2.4(8) . . . . ? C4A C4B C8A C8 179.3(5) . . . . ? C5 C4B C8A C9 178.2(5) . . . . ? C4A C4B C8A C9 -0.1(7) . . . . ? C8 C8A C9 C10 178.7(6) . . . . ? C4B C8A C9 C10 -1.9(8) . . . . ? C8A C9 C10 C10A 1.6(9) . . . . ? C4B C4A C10A C10 -2.8(7) . . . . ? C4 C4A C10A C10 -179.3(5) . . . . ? C4B C4A C10A C1 174.3(4) . . . . ? C4 C4A C10A C1 -2.1(8) . . . . ? C9 C10 C10A C4A 0.9(8) . . . . ? C9 C10 C10A C1 -176.4(5) . . . . ? O1 C1 C10A C4A 97.0(5) . . . . ? C2 C1 C10A C4A -20.5(7) . . . . ? O1 C1 C10A C10 -85.8(5) . . . . ? C2 C1 C10A C10 156.7(5) . . . . ? C10A C1 O1 C11 144.8(4) . . . . ? C2 C1 O1 C11 -96.7(5) . . . . ? C1 O1 C11 O11 -0.9(8) . . . . ? C1 O1 C11 C12 -178.5(4) . . . . ? O11 C11 C12 O12 161.3(5) . . . . ? O1 C11 C12 O12 -20.9(6) . . . . ? O11 C11 C12 C13 39.5(8) . . . . ? O1 C11 C12 C13 -142.7(5) . . . . ? O11 C11 C12 C17 -82.8(7) . . . . ? O1 C11 C12 C17 95.0(6) . . . . ? C11 C12 O12 C20 160.6(5) . . . . ? C13 C12 O12 C20 -71.3(5) . . . . ? C17 C12 O12 C20 36.1(5) . . . . ? O12 C12 C13 C14 68.7(6) . . . . ? C11 C12 C13 C14 -166.1(5) . . . . ? C17 C12 C13 C14 -37.3(6) . . . . ? C12 C13 C14 C15 2.3(7) . . . . ? C13 C14 C15 C17 34.4(7) . . . . ? C13 C14 C15 C20 -69.1(6) . . . . ? C13 C14 C15 C16 167.9(6) . . . . ? C20 C15 C17 C19 -64.7(6) . . . . ? C16 C15 C17 C19 60.0(8) . . . . ? C14 C15 C17 C19 -169.7(5) . . . . ? C20 C15 C17 C18 168.2(5) . . . . ? C16 C15 C17 C18 -67.1(8) . . . . ? C14 C15 C17 C18 63.2(6) . . . . ? C20 C15 C17 C12 51.0(5) . . . . ? C16 C15 C17 C12 175.7(6) . . . . ? C14 C15 C17 C12 -54.0(5) . . . . ? O12 C12 C17 C15 -53.5(5) . . . . ? C11 C12 C17 C15 -175.3(5) . . . . ? C13 C12 C17 C15 55.6(5) . . . . ? O12 C12 C17 C19 64.4(6) . . . . ? C11 C12 C17 C19 -57.4(7) . . . . ? C13 C12 C17 C19 173.4(5) . . . . ? O12 C12 C17 C18 -171.4(5) . . . . ? C11 C12 C17 C18 66.8(7) . . . . ? C13 C12 C17 C18 -62.3(6) . . . . ? C12 O12 C20 O20 176.2(6) . . . . ? C12 O12 C20 C15 -1.4(6) . . . . ? C17 C15 C20 O20 148.2(8) . . . . ? C16 C15 C20 O20 19.0(10) . . . . ? C14 C15 C20 O20 -104.7(8) . . . . ? C17 C15 C20 O12 -34.5(6) . . . . ? C16 C15 C20 O12 -163.7(5) . . . . ? C14 C15 C20 O12 72.5(6) . . . . ? C3 C2 O2 C21 -154.5(4) . . . . ? C1 C2 O2 C21 84.9(5) . . . . ? C2 O2 C21 O21 -1.5(7) . . . . ? C2 O2 C21 C22 174.4(4) . . . . ? O21 C21 C22 O22 -6.1(8) . . . . ? O2 C21 C22 O22 178.2(4) . . . . ? O21 C21 C22 C23 -128.0(7) . . . . ? O2 C21 C22 C23 56.3(6) . . . . ? O21 C21 C22 C27 106.1(7) . . . . ? O2 C21 C22 C27 -69.7(6) . . . . ? C21 C22 O22 C30 156.0(4) . . . . ? C23 C22 O22 C30 -74.0(5) . . . . ? C27 C22 O22 C30 35.1(5) . . . . ? O22 C22 C23 C24 68.5(6) . . . . ? C21 C22 C23 C24 -169.7(5) . . . . ? C27 C22 C23 C24 -38.9(6) . . . . ? C22 C23 C24 C25 2.5(6) . . . . ? C23 C24 C25 C30 -68.0(6) . . . . ? C23 C24 C25 C26 165.1(6) . . . . ? C23 C24 C25 C27 34.4(6) . . . . ? C30 C25 C27 C28 170.1(5) . . . . ? C26 C25 C27 C28 -63.1(7) . . . . ? C24 C25 C27 C28 64.4(6) . . . . ? C30 C25 C27 C29 -63.8(6) . . . . ? C26 C25 C27 C29 63.1(7) . . . . ? C24 C25 C27 C29 -169.4(5) . . . . ? C30 C25 C27 C22 51.5(5) . . . . ? C26 C25 C27 C22 178.3(5) . . . . ? C24 C25 C27 C22 -54.2(5) . . . . ? O22 C22 C27 C28 -170.2(4) . . . . ? C21 C22 C27 C28 74.9(6) . . . . ? C23 C22 C27 C28 -58.9(6) . . . . ? O22 C22 C27 C29 62.0(5) . . . . ? C21 C22 C27 C29 -52.9(6) . . . . ? C23 C22 C27 C29 173.3(5) . . . . ? O22 C22 C27 C25 -53.2(4) . . . . ? C21 C22 C27 C25 -168.1(5) . . . . ? C23 C22 C27 C25 58.0(5) . . . . ? C22 O22 C30 O30 179.3(5) . . . . ? C22 O22 C30 C25 0.7(5) . . . . ? C26 C25 C30 O30 16.3(9) . . . . ? C27 C25 C30 O30 145.5(6) . . . . ? C24 C25 C30 O30 -109.7(7) . . . . ? C26 C25 C30 O22 -165.3(5) . . . . ? C27 C25 C30 O22 -36.0(5) . . . . ? C24 C25 C30 O22 68.8(5) . . . . ? O1' C1' C2' O2' 53.4(5) . . . . ? C10" C1' C2' O2' 169.0(4) . . . . ? O1' C1' C2' C3' -66.7(5) . . . . ? C10" C1' C2' C3' 48.9(6) . . . . ? O2' C2' C3' C4' 176.5(4) . . . . ? C1' C2' C3' C4' -63.0(6) . . . . ? C2' C3' C4' C4A' 44.9(7) . . . . ? C3' C4' C4A' C10" -15.7(8) . . . . ? C3' C4' C4A' C4B' 166.0(5) . . . . ? C10" C4A' C4B' C5' -178.6(5) . . . . ? C4' C4A' C4B' C5' -0.4(8) . . . . ? C10" C4A' C4B' C8A' 2.1(7) . . . . ? C4' C4A' C4B' C8A' -179.6(5) . . . . ? C4A' C4B' C5' C6' -177.3(5) . . . . ? C8A' C4B' C5' C6' 1.9(8) . . . . ? C4B' C5' C6' C7' -1.8(9) . . . . ? C5' C6' C7' C8' 0.0(10) . . . . ? C6' C7' C8' C8A' 1.6(10) . . . . ? C5' C4B' C8A' C9' 179.4(5) . . . . ? C4A' C4B' C8A' C9' -1.3(7) . . . . ? C5' C4B' C8A' C8' -0.3(7) . . . . ? C4A' C4B' C8A' C8' 178.9(5) . . . . ? C7' C8' C8A' C9' 178.8(6) . . . . ? C7' C8' C8A' C4B' -1.5(8) . . . . ? C4B' C8A' C9' C10' -0.2(8) . . . . ? C8' C8A' C9' C10' 179.6(5) . . . . ? C8A' C9' C10' C10" 0.8(9) . . . . ? C4B' C4A' C10" C10' -1.5(7) . . . . ? C4' C4A' C10" C10' -179.7(5) . . . . ? C4B' C4A' C10" C1' -179.4(5) . . . . ? C4' C4A' C10" C1' 2.4(8) . . . . ? C9' C10' C10" C4A' 0.0(8) . . . . ? C9' C10' C10" C1' 178.0(5) . . . . ? O1' C1' C10" C4A' 98.8(5) . . . . ? C2' C1' C10" C4A' -18.6(7) . . . . ? O1' C1' C10" C10' -79.1(5) . . . . ? C2' C1' C10" C10' 163.5(5) . . . . ? C10" C1' O1' C11' 140.5(4) . . . . ? C2' C1' O1' C11' -100.6(5) . . . . ? C1' O1' C11' O11' 2.2(8) . . . . ? C1' O1' C11' C12' -174.5(4) . . . . ? O11' C11' C12' O12' 160.5(5) . . . . ? O1' C11' C12' O12' -22.7(6) . . . . ? O11' C11' C12' C13' 40.9(8) . . . . ? O1' C11' C12' C13' -142.4(5) . . . . ? O11' C11' C12' C17' -83.5(7) . . . . ? O1' C11' C12' C17' 93.2(5) . . . . ? C11' C12' O12' C20' 161.5(4) . . . . ? C13' C12' O12' C20' -72.4(5) . . . . ? C17' C12' O12' C20' 36.4(5) . . . . ? O12' C12' C13' C14' 70.5(6) . . . . ? C11' C12' C13' C14' -167.1(5) . . . . ? C17' C12' C13' C14' -36.5(6) . . . . ? C12' C13' C14' C15' 0.5(6) . . . . ? C13' C14' C15' C20' -67.7(6) . . . . ? C13' C14' C15' C16' 166.8(6) . . . . ? C13' C14' C15' C17' 35.4(6) . . . . ? C20' C15' C17' C19' -67.1(6) . . . . ? C16' C15' C17' C19' 58.8(7) . . . . ? C14' C15' C17' C19' -171.5(5) . . . . ? C20' C15' C17' C18' 167.1(5) . . . . ? C16' C15' C17' C18' -66.9(7) . . . . ? C14' C15' C17' C18' 62.8(6) . . . . ? C20' C15' C17' C12' 50.2(5) . . . . ? C16' C15' C17' C12' 176.1(5) . . . . ? C14' C15' C17' C12' -54.1(5) . . . . ? O12' C12' C17' C19' 64.7(5) . . . . ? C11' C12' C17' C19' -55.9(6) . . . . ? C13' C12' C17' C19' 174.0(5) . . . . ? O12' C12' C17' C18' -172.0(4) . . . . ? C11' C12' C17' C18' 67.4(6) . . . . ? C13' C12' C17' C18' -62.7(6) . . . . ? O12' C12' C17' C15' -53.1(4) . . . . ? C11' C12' C17' C15' -173.6(4) . . . . ? C13' C12' C17' C15' 56.3(5) . . . . ? C12' O12' C20' O20' 176.9(6) . . . . ? C12' O12' C20' C15' -1.9(6) . . . . ? C16' C15' C20' O20' 19.4(10) . . . . ? C17' C15' C20' O20' 148.2(7) . . . . ? C14' C15' C20' O20' -106.9(7) . . . . ? C16' C15' C20' O12' -161.9(5) . . . . ? C17' C15' C20' O12' -33.1(5) . . . . ? C14' C15' C20' O12' 71.8(5) . . . . ? C3' C2' O2' C21' -151.6(5) . . . . ? C1' C2' O2' C21' 86.2(5) . . . . ? C2' O2' C21' O21' -3.2(8) . . . . ? C2' O2' C21' C22' 175.9(4) . . . . ? O21' C21' C22' O22' -5.1(8) . . . . ? O2' C21' C22' O22' 175.8(5) . . . . ? O21' C21' C22' C27' 114.4(7) . . . . ? O2' C21' C22' C27' -64.6(6) . . . . ? O21' C21' C22' C23' -125.5(7) . . . . ? O2' C21' C22' C23' 55.5(7) . . . . ? C21' C22' O22' C30' 156.7(6) . . . . ? C27' C22' O22' C30' 29.1(7) . . . . ? C23' C22' O22' C30' -76.1(7) . . . . ? O22' C22' C23' C24' 69.1(8) . . . . ? C21' C22' C23' C24' -169.4(6) . . . . ? C27' C22' C23' C24' -40.0(8) . . . . ? C22' C23' C24' C25' 1.6(9) . . . . ? C23' C24' C25' C30' -66.7(8) . . . . ? C23' C24' C25' C26' 164.9(7) . . . . ? C23' C24' C25' C27' 35.8(8) . . . . ? O22' C22' C27' C28' -173.5(6) . . . . ? C21' C22' C27' C28' 65.3(8) . . . . ? C23' C22' C27' C28' -63.6(7) . . . . ? O22' C22' C27' C25' -49.0(5) . . . . ? C21' C22' C27' C25' -170.2(5) . . . . ? C23' C22' C27' C25' 60.9(5) . . . . ? O22' C22' C27' C29' 63.8(6) . . . . ? C21' C22' C27' C29' -57.4(7) . . . . ? C23' C22' C27' C29' 173.7(6) . . . . ? C30' C25' C27' C28' 176.9(7) . . . . ? C26' C25' C27' C28' -57.8(9) . . . . ? C24' C25' C27' C28' 67.4(8) . . . . ? C30' C25' C27' C22' 50.1(6) . . . . ? C26' C25' C27' C22' 175.4(6) . . . . ? C24' C25' C27' C22' -59.4(6) . . . . ? C30' C25' C27' C29' -60.6(7) . . . . ? C26' C25' C27' C29' 64.6(8) . . . . ? C24' C25' C27' C29' -170.2(6) . . . . ? C22' O22' C30' O30' 179.4(9) . . . . ? C22' O22' C30' C25' 6.5(9) . . . . ? C26' C25' C30' O30' 21.7(16) . . . . ? C24' C25' C30' O30' -106.7(13) . . . . ? C27' C25' C30' O30' 150.7(12) . . . . ? C26' C25' C30' O22' -166.7(7) . . . . ? C24' C25' C30' O22' 65.0(8) . . . . ? C27' C25' C30' O22' -37.7(8) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 23.31 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.592 _refine_diff_density_min -0.428 _refine_diff_density_rms 0.063