# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Prof Antonio Togni' _publ_contact_author_email TOGNI@INORG.CHEM.ETHZ.CH _publ_section_title ; Ni(II)-Catalyzed Enantioselective Nazarov Cyclizations ; loop_ _publ_author_name 'A. Togni' 'Irene Walz' # Attachment 'Compound_5.cif' data_IWA_139_2 _database_code_depnum_ccdc_archive 'CCDC 682373' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C32 H40 O6' _chemical_formula_sum 'C32 H40 O6' _chemical_formula_weight 520.64 _chemical_absolute_configuration rm 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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_int_tables_number 19 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 10.0389(5) _cell_length_b 15.9508(7) _cell_length_c 18.4174(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2949.2(2) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description cube _exptl_crystal_colour colourless _exptl_crystal_size_max 0.51 _exptl_crystal_size_mid 0.44 _exptl_crystal_size_min 0.40 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.173 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1120 _exptl_absorpt_coefficient_mu 0.080 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9602 _exptl_absorpt_correction_T_max 0.9691 _exptl_absorpt_process_details 'Sadabs vers. 2.03' _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(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 120948 _diffrn_reflns_av_R_equivalents 0.0493 _diffrn_reflns_av_sigmaI/netI 0.0234 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 1.69 _diffrn_reflns_theta_max 36.35 _reflns_number_total 14329 _reflns_number_gt 12741 _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^)+(0.0789P)^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 riding _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 0.8(4) _refine_ls_number_reflns 14329 _refine_ls_number_parameters 504 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0503 _refine_ls_R_factor_gt 0.0440 _refine_ls_wR_factor_ref 0.1140 _refine_ls_wR_factor_gt 0.1089 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.037 _refine_ls_shift/su_max 0.003 _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 0.44053(8) 0.53059(5) -0.12380(3) 0.03933(15) Uani 1 1 d . . . O2 O 0.56785(7) 0.30683(4) -0.00300(3) 0.03261(13) Uani 1 1 d . . . O3 O 0.45221(10) 0.13296(5) 0.20304(5) 0.0479(2) Uani 1 1 d . . . O4 O 0.31081(7) 0.41637(4) 0.18492(3) 0.03152(12) Uani 1 1 d . . . O5 O 0.13406(7) 0.46520(4) -0.01106(5) 0.03999(16) Uani 1 1 d . . . O6 O 0.25640(6) 0.57783(3) 0.01940(4) 0.03070(12) Uani 1 1 d . . . C1 C 0.37286(7) 0.45582(4) -0.01429(4) 0.02141(10) Uani 1 1 d . . . H1A H 0.3530(15) 0.4020(9) -0.0358(8) 0.032(3) Uiso 1 1 d . . . C2 C 0.45000(7) 0.44627(4) 0.05786(3) 0.01954(10) Uani 1 1 d . . . H2A H 0.4176(12) 0.4870(7) 0.0921(6) 0.021(2) Uiso 1 1 d . . . C3 C 0.59102(7) 0.47368(4) 0.03853(4) 0.02091(10) Uani 1 1 d . . . C4 C 0.60052(7) 0.50463(5) -0.02956(4) 0.02413(11) Uani 1 1 d . . . C5 C 0.46964(8) 0.50205(5) -0.06447(4) 0.02464(12) Uani 1 1 d . . . C6 C 0.71933(10) 0.53963(7) -0.06771(5) 0.03806(19) Uani 1 1 d . . . H6A H 0.773(2) 0.4959(14) -0.0948(11) 0.066(5) Uiso 1 1 d . . . H6B H 0.6859(18) 0.5819(12) -0.1062(10) 0.054(4) Uiso 1 1 d . . . H6C H 0.784(2) 0.5588(13) -0.0308(11) 0.064(5) Uiso 1 1 d . . . C7 C 0.69585(7) 0.46700(5) 0.09383(4) 0.02489(12) Uani 1 1 d . . . C8 C 0.82415(9) 0.43934(8) 0.07812(6) 0.03827(19) Uani 1 1 d . . . H8A H 0.848(2) 0.4303(15) 0.0312(12) 0.069(6) Uiso 1 1 d . . . C9 C 0.91824(11) 0.43172(10) 0.13336(7) 0.0505(3) Uani 1 1 d . . . H9A H 1.004(3) 0.4113(19) 0.1241(16) 0.107(9) Uiso 1 1 d . . . C10 C 0.88605(12) 0.45167(10) 0.20421(7) 0.0510(3) Uani 1 1 d . . . H10A H 0.943(2) 0.4503(15) 0.2412(13) 0.078(7) Uiso 1 1 d . . . C11 C 0.76041(12) 0.48260(11) 0.21948(6) 0.0545(3) Uani 1 1 d . . . H11A H 0.745(2) 0.4988(17) 0.2690(13) 0.080(6) Uiso 1 1 d . . . C12 C 0.66628(10) 0.48925(9) 0.16511(5) 0.0428(2) Uani 1 1 d . . . H12A H 0.5810(18) 0.5023(12) 0.1769(9) 0.050(4) Uiso 1 1 d . . . C13 C 0.44416(7) 0.36064(4) 0.09280(4) 0.02072(10) Uani 1 1 d . . . C14 C 0.51079(7) 0.29198(4) 0.06285(4) 0.02367(11) Uani 1 1 d . . . C15 C 0.51709(9) 0.21400(5) 0.09737(4) 0.02846(13) Uani 1 1 d . . . H15A H 0.5533(16) 0.1706(10) 0.0746(8) 0.039(3) Uiso 1 1 d . . . C16 C 0.45198(9) 0.20541(5) 0.16356(5) 0.03048(14) Uani 1 1 d . . . C17 C 0.37909(9) 0.27090(5) 0.19393(4) 0.02913(14) Uani 1 1 d . . . H17A H 0.3319(15) 0.2600(9) 0.2389(8) 0.035(3) Uiso 1 1 d . . . C18 C 0.37689(7) 0.34790(4) 0.15864(4) 0.02333(11) Uani 1 1 d . . . C19 C 0.66295(16) 0.24843(7) -0.02937(8) 0.0539(3) Uani 1 1 d . . . H19A H 0.737(3) 0.2352(17) 0.0077(14) 0.084(7) Uiso 1 1 d . . . H19B H 0.623(2) 0.1948(14) -0.0367(11) 0.064(5) Uiso 1 1 d . . . H19C H 0.6848(19) 0.2673(12) -0.0707(10) 0.052(4) Uiso 1 1 d . . . C20 C 0.53986(17) 0.06857(7) 0.18051(8) 0.0558(4) Uani 1 1 d . . . H20A H 0.540(2) 0.0281(14) 0.2190(13) 0.074(6) Uiso 1 1 d . . . H20B H 0.6334(19) 0.0876(11) 0.1770(9) 0.048(4) Uiso 1 1 d . . . H20C H 0.528(3) 0.0490(15) 0.1321(13) 0.076(6) Uiso 1 1 d . . . C21 C 0.23736(10) 0.40711(6) 0.25032(5) 0.03444(17) Uani 1 1 d . . . H21A H 0.1701(18) 0.3655(11) 0.2436(9) 0.048(4) Uiso 1 1 d . . . H21B H 0.2006(15) 0.4620(10) 0.2619(8) 0.037(3) Uiso 1 1 d . . . H21C H 0.2934(16) 0.3933(10) 0.2878(9) 0.042(4) Uiso 1 1 d . . . C22 C 0.24050(7) 0.49903(4) -0.00339(4) 0.02338(11) Uani 1 1 d . . . C23 C 0.13961(8) 0.62087(5) 0.04911(5) 0.02944(14) Uani 1 1 d . . . H23A H 0.0614(13) 0.5905(8) 0.0345(7) 0.024(3) Uiso 1 1 d . . . H23B H 0.2150(15) 0.7383(9) 0.0344(8) 0.035(3) Uiso 1 1 d . . . C24 C 0.13415(8) 0.70964(4) 0.01853(5) 0.02779(13) Uani 1 1 d . . . C25 C 0.01609(11) 0.75444(6) 0.05529(6) 0.03830(19) Uani 1 1 d . . . H25A H 0.0146(16) 0.8101(10) 0.0399(8) 0.036(3) Uiso 1 1 d . . . H25B H -0.0688(17) 0.7281(11) 0.0405(9) 0.041(4) Uiso 1 1 d . . . C26 C 0.02678(16) 0.75412(7) 0.13761(6) 0.0491(3) Uani 1 1 d . . . H26A H -0.062(2) 0.7825(14) 0.1603(12) 0.065(5) Uiso 1 1 d . . . H26B H 0.0982(19) 0.7828(12) 0.1557(10) 0.053(5) Uiso 1 1 d . . . C27 C 0.03767(16) 0.66524(8) 0.16798(7) 0.0507(3) Uani 1 1 d . . . H27A H -0.047(2) 0.6334(14) 0.1558(12) 0.068(6) Uiso 1 1 d . . . C28 C 0.15377(13) 0.62013(6) 0.13127(6) 0.0414(2) Uani 1 1 d . . . H28A H 0.1589(18) 0.5649(12) 0.1470(10) 0.051(4) Uiso 1 1 d . . . H28B H 0.2371(19) 0.6465(11) 0.1418(9) 0.046(4) Uiso 1 1 d . . . C29 C 0.12979(8) 0.71288(5) -0.06521(5) 0.02946(14) Uani 1 1 d . . . H29A H 0.2095(14) 0.6845(9) -0.0808(7) 0.030(3) Uiso 1 1 d . . . C30 C 0.13667(14) 0.80315(6) -0.09263(6) 0.0413(2) Uani 1 1 d . . . H30A H 0.064(2) 0.8333(14) -0.0806(11) 0.064(5) Uiso 1 1 d . . . H30B H 0.151(2) 0.8055(12) -0.1420(11) 0.055(5) Uiso 1 1 d . . . H30C H 0.207(2) 0.8363(13) -0.0674(11) 0.059(5) Uiso 1 1 d . . . C31 C 0.00904(11) 0.66831(7) -0.09804(6) 0.03994(19) Uani 1 1 d . . . H31A H 0.0137(19) 0.6720(11) -0.1505(10) 0.050(4) Uiso 1 1 d . . . H31B H -0.068(2) 0.6899(13) -0.0833(11) 0.064(5) Uiso 1 1 d . . . H31C H 0.002(2) 0.6087(13) -0.0823(12) 0.066(6) Uiso 1 1 d . . . C32 C 0.0542(3) 0.66647(13) 0.25044(8) 0.0795(7) Uani 1 1 d . . . H32A H 0.133(2) 0.6891(15) 0.2657(12) 0.063(6) Uiso 1 1 d . . . H32B H 0.064(3) 0.6104(16) 0.2699(15) 0.086(7) Uiso 1 1 d . . . H32C H -0.010(3) 0.7014(18) 0.2773(17) 0.106(9) 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 O1 0.0443(4) 0.0504(4) 0.0233(2) 0.0109(3) -0.0038(2) 0.0016(3) O2 0.0454(3) 0.0237(2) 0.0287(2) 0.00299(19) 0.0169(2) 0.0095(2) O3 0.0672(5) 0.0299(3) 0.0466(4) 0.0191(3) 0.0215(4) 0.0134(3) O4 0.0392(3) 0.0278(2) 0.0276(2) 0.0026(2) 0.0159(2) 0.0073(2) O5 0.0249(2) 0.0313(3) 0.0638(5) -0.0134(3) -0.0038(3) -0.0014(2) O6 0.0235(2) 0.0190(2) 0.0496(3) -0.0052(2) 0.0043(2) 0.00224(17) C1 0.0235(3) 0.0189(2) 0.0218(2) -0.00047(19) -0.0005(2) 0.00323(19) C2 0.0211(2) 0.0183(2) 0.0192(2) 0.00088(18) 0.00269(19) 0.00245(18) C3 0.0219(2) 0.0210(2) 0.0198(2) 0.00123(19) 0.00224(19) 0.00127(19) C4 0.0265(3) 0.0255(3) 0.0205(2) 0.0027(2) 0.0038(2) 0.0004(2) C5 0.0299(3) 0.0245(3) 0.0195(2) 0.0014(2) 0.0012(2) 0.0033(2) C6 0.0337(4) 0.0479(5) 0.0326(4) 0.0109(3) 0.0108(3) -0.0044(3) C7 0.0226(3) 0.0287(3) 0.0233(3) 0.0021(2) -0.0001(2) -0.0002(2) C8 0.0249(3) 0.0546(5) 0.0354(4) -0.0037(4) -0.0005(3) 0.0066(3) C9 0.0269(4) 0.0776(8) 0.0470(5) -0.0028(5) -0.0067(4) 0.0110(5) C10 0.0341(5) 0.0776(8) 0.0412(5) 0.0028(5) -0.0143(4) 0.0050(5) C11 0.0411(5) 0.0960(10) 0.0263(4) -0.0033(5) -0.0073(4) 0.0118(6) C12 0.0320(4) 0.0740(7) 0.0224(3) -0.0013(4) -0.0021(3) 0.0123(4) C13 0.0227(2) 0.0193(2) 0.0202(2) 0.00222(18) 0.0041(2) 0.00288(19) C14 0.0267(3) 0.0203(2) 0.0239(3) 0.0023(2) 0.0056(2) 0.0040(2) C15 0.0339(3) 0.0209(3) 0.0306(3) 0.0039(2) 0.0069(3) 0.0056(2) C16 0.0363(4) 0.0242(3) 0.0310(3) 0.0091(2) 0.0065(3) 0.0038(3) C17 0.0355(4) 0.0267(3) 0.0252(3) 0.0069(2) 0.0080(3) 0.0023(3) C18 0.0249(3) 0.0234(3) 0.0217(2) 0.0024(2) 0.0051(2) 0.0024(2) C19 0.0732(8) 0.0326(4) 0.0558(6) 0.0044(4) 0.0397(6) 0.0179(5) C20 0.0731(8) 0.0335(4) 0.0609(7) 0.0230(5) 0.0235(6) 0.0210(5) C21 0.0361(4) 0.0416(4) 0.0256(3) 0.0034(3) 0.0126(3) 0.0075(3) C22 0.0231(3) 0.0198(2) 0.0272(3) -0.0004(2) -0.0014(2) 0.0026(2) C23 0.0267(3) 0.0214(3) 0.0402(4) -0.0004(3) 0.0059(3) 0.0048(2) C24 0.0293(3) 0.0203(3) 0.0338(3) -0.0017(2) 0.0044(3) 0.0034(2) C25 0.0455(5) 0.0298(4) 0.0396(4) 0.0017(3) 0.0115(4) 0.0157(3) C26 0.0745(8) 0.0355(4) 0.0372(4) 0.0003(4) 0.0174(5) 0.0198(5) C27 0.0718(8) 0.0394(5) 0.0408(5) 0.0073(4) 0.0198(5) 0.0177(5) C28 0.0527(6) 0.0315(4) 0.0402(5) 0.0059(3) 0.0066(4) 0.0121(4) C29 0.0287(3) 0.0247(3) 0.0350(3) -0.0038(3) 0.0045(3) 0.0009(2) C30 0.0579(6) 0.0293(4) 0.0366(4) 0.0025(3) 0.0022(4) -0.0014(4) C31 0.0330(4) 0.0416(5) 0.0452(5) -0.0079(4) -0.0009(4) -0.0033(3) C32 0.134(2) 0.0643(9) 0.0402(6) 0.0103(6) 0.0229(10) 0.0315(12) _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 1.2193(9) . ? O2 C14 1.3621(9) . ? O2 C19 1.4194(11) . ? O3 C16 1.3654(10) . ? O3 C20 1.4146(14) . ? O4 C18 1.3665(9) . ? O4 C21 1.4199(10) . ? O5 C22 1.2054(10) . ? O6 C22 1.3348(9) . ? O6 C23 1.4646(10) . ? C1 C22 1.5102(9) . ? C1 C5 1.5303(10) . ? C1 C2 1.5456(9) . ? C2 C13 1.5111(9) . ? C2 C3 1.5239(9) . ? C3 C4 1.3512(9) . ? C3 C7 1.4683(10) . ? C4 C5 1.4633(11) . ? C4 C6 1.4925(11) . ? C7 C12 1.3919(12) . ? C7 C8 1.3920(12) . ? C8 C9 1.3935(15) . ? C9 C10 1.3815(19) . ? C10 C11 1.3831(17) . ? C11 C12 1.3809(14) . ? C13 C14 1.3968(9) . ? C13 C18 1.4027(9) . ? C14 C15 1.3984(10) . ? C15 C16 1.3899(11) . ? C16 C17 1.3926(11) . ? C17 C18 1.3897(10) . ? C23 C28 1.5199(14) . ? C23 C24 1.5249(11) . ? C24 C25 1.5407(12) . ? C24 C29 1.5436(12) . ? C25 C26 1.5199(15) . ? C26 C27 1.5280(15) . ? C27 C28 1.5275(16) . ? C27 C32 1.528(2) . ? C29 C30 1.5274(13) . ? C29 C31 1.5299(14) . ? 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 C14 O2 C19 118.26(7) . . ? C16 O3 C20 117.35(8) . . ? C18 O4 C21 117.99(6) . . ? C22 O6 C23 117.58(6) . . ? C22 C1 C5 114.77(6) . . ? C22 C1 C2 111.81(5) . . ? C5 C1 C2 104.40(5) . . ? C13 C2 C3 113.26(5) . . ? C13 C2 C1 115.84(6) . . ? C3 C2 C1 103.67(5) . . ? C4 C3 C7 128.30(6) . . ? C4 C3 C2 112.78(6) . . ? C7 C3 C2 118.88(6) . . ? C3 C4 C5 109.52(6) . . ? C3 C4 C6 129.04(7) . . ? C5 C4 C6 121.42(7) . . ? O1 C5 C4 126.76(7) . . ? O1 C5 C1 124.68(7) . . ? C4 C5 C1 108.56(6) . . ? C12 C7 C8 118.30(8) . . ? C12 C7 C3 118.87(7) . . ? C8 C7 C3 122.82(7) . . ? C7 C8 C9 120.21(9) . . ? C10 C9 C8 120.73(10) . . ? C9 C10 C11 119.18(10) . . ? C12 C11 C10 120.27(10) . . ? C11 C12 C7 121.22(9) . . ? C14 C13 C18 117.29(6) . . ? C14 C13 C2 121.46(6) . . ? C18 C13 C2 121.18(6) . . ? O2 C14 C13 114.63(6) . . ? O2 C14 C15 122.72(6) . . ? C13 C14 C15 122.64(6) . . ? C16 C15 C14 117.72(7) . . ? O3 C16 C15 123.34(7) . . ? O3 C16 C17 114.96(7) . . ? C15 C16 C17 121.69(6) . . ? C18 C17 C16 118.91(6) . . ? O4 C18 C17 123.26(6) . . ? O4 C18 C13 115.10(6) . . ? C17 C18 C13 121.64(6) . . ? O5 C22 O6 124.36(7) . . ? O5 C22 C1 124.06(7) . . ? O6 C22 C1 111.49(6) . . ? O6 C23 C28 107.06(7) . . ? O6 C23 C24 109.03(6) . . ? C28 C23 C24 112.22(7) . . ? C23 C24 C25 107.22(7) . . ? C23 C24 C29 113.65(6) . . ? C25 C24 C29 113.69(7) . . ? C26 C25 C24 112.49(9) . . ? C25 C26 C27 111.92(9) . . ? C28 C27 C32 111.31(14) . . ? C28 C27 C26 109.25(10) . . ? C32 C27 C26 111.08(12) . . ? C23 C28 C27 111.45(9) . . ? C30 C29 C31 110.07(9) . . ? C30 C29 C24 111.14(7) . . ? C31 C29 C24 113.69(8) . . ? 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 C22 C1 C2 C13 101.03(6) . . . . ? C5 C1 C2 C13 -134.32(6) . . . . ? C22 C1 C2 C3 -134.27(6) . . . . ? C5 C1 C2 C3 -9.61(6) . . . . ? C13 C2 C3 C4 132.79(6) . . . . ? C1 C2 C3 C4 6.43(7) . . . . ? C13 C2 C3 C7 -49.36(8) . . . . ? C1 C2 C3 C7 -175.72(6) . . . . ? C7 C3 C4 C5 -177.70(7) . . . . ? C2 C3 C4 C5 -0.10(8) . . . . ? C7 C3 C4 C6 0.67(14) . . . . ? C2 C3 C4 C6 178.28(8) . . . . ? C3 C4 C5 O1 174.28(8) . . . . ? C6 C4 C5 O1 -4.24(13) . . . . ? C3 C4 C5 C1 -6.50(8) . . . . ? C6 C4 C5 C1 174.98(7) . . . . ? C22 C1 C5 O1 -47.91(10) . . . . ? C2 C1 C5 O1 -170.66(8) . . . . ? C22 C1 C5 C4 132.85(6) . . . . ? C2 C1 C5 C4 10.11(7) . . . . ? C4 C3 C7 C12 136.45(10) . . . . ? C2 C3 C7 C12 -41.03(11) . . . . ? C4 C3 C7 C8 -43.51(12) . . . . ? C2 C3 C7 C8 139.01(9) . . . . ? C12 C7 C8 C9 2.14(17) . . . . ? C3 C7 C8 C9 -177.91(11) . . . . ? C7 C8 C9 C10 -0.2(2) . . . . ? C8 C9 C10 C11 -2.5(2) . . . . ? C9 C10 C11 C12 3.4(3) . . . . ? C10 C11 C12 C7 -1.4(2) . . . . ? C8 C7 C12 C11 -1.32(19) . . . . ? C3 C7 C12 C11 178.72(12) . . . . ? C3 C2 C13 C14 -48.59(9) . . . . ? C1 C2 C13 C14 71.01(9) . . . . ? C3 C2 C13 C18 128.22(7) . . . . ? C1 C2 C13 C18 -112.18(7) . . . . ? C19 O2 C14 C13 165.27(10) . . . . ? C19 O2 C14 C15 -15.42(14) . . . . ? C18 C13 C14 O2 176.46(7) . . . . ? C2 C13 C14 O2 -6.60(11) . . . . ? C18 C13 C14 C15 -2.85(12) . . . . ? C2 C13 C14 C15 174.08(7) . . . . ? O2 C14 C15 C16 -178.22(8) . . . . ? C13 C14 C15 C16 1.04(13) . . . . ? C20 O3 C16 C15 10.04(17) . . . . ? C20 O3 C16 C17 -170.99(12) . . . . ? C14 C15 C16 O3 -179.08(9) . . . . ? C14 C15 C16 C17 2.01(14) . . . . ? O3 C16 C17 C18 177.92(9) . . . . ? C15 C16 C17 C18 -3.09(14) . . . . ? C21 O4 C18 C17 -2.15(13) . . . . ? C21 O4 C18 C13 178.18(8) . . . . ? C16 C17 C18 O4 -178.50(8) . . . . ? C16 C17 C18 C13 1.14(13) . . . . ? C14 C13 C18 O4 -178.60(7) . . . . ? C2 C13 C18 O4 4.45(10) . . . . ? C14 C13 C18 C17 1.73(11) . . . . ? C2 C13 C18 C17 -175.22(7) . . . . ? C23 O6 C22 O5 11.30(12) . . . . ? C23 O6 C22 C1 -165.43(7) . . . . ? C5 C1 C22 O5 128.97(9) . . . . ? C2 C1 C22 O5 -112.37(9) . . . . ? C5 C1 C22 O6 -54.28(8) . . . . ? C2 C1 C22 O6 64.38(8) . . . . ? C22 O6 C23 C28 102.35(9) . . . . ? C22 O6 C23 C24 -136.03(7) . . . . ? O6 C23 C24 C25 -176.02(8) . . . . ? C28 C23 C24 C25 -57.58(10) . . . . ? O6 C23 C24 C29 57.48(9) . . . . ? C28 C23 C24 C29 175.91(8) . . . . ? C23 C24 C25 C26 56.48(11) . . . . ? C29 C24 C25 C26 -177.04(9) . . . . ? C24 C25 C26 C27 -56.96(15) . . . . ? C25 C26 C27 C28 54.45(17) . . . . ? C25 C26 C27 C32 177.63(16) . . . . ? O6 C23 C28 C27 178.90(9) . . . . ? C24 C23 C28 C27 59.32(12) . . . . ? C32 C27 C28 C23 -178.45(14) . . . . ? C26 C27 C28 C23 -55.41(15) . . . . ? C23 C24 C29 C30 -175.06(8) . . . . ? C25 C24 C29 C30 61.92(10) . . . . ? C23 C24 C29 C31 60.10(10) . . . . ? C25 C24 C29 C31 -62.93(10) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 36.35 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.444 _refine_diff_density_min -0.135 _refine_diff_density_rms 0.059