Electronic Supplementary Material for Organic & Biomolecular Chemistry This journal is © The Royal Society of Chemistry 2005 data_global _journal_coden_Cambridge 177 loop_ _publ_author_name 'Jonathan White' 'Goh Yit Wooi' _publ_contact_author_name 'Dr Jonathan White' _publ_contact_author_address ; Chemistry University of Melbourne Melbourne Victoria 3010 AUSTRALIA ; _publ_contact_author_email WHITEJM@UNIMELB.EDU.AU _publ_requested_journal 'Organic & Biomolecular Chemistry' _publ_section_title ; Structural Manifestations of the Cheletropic Reaction ; data_jmwrg66 _database_code_depnum_ccdc_archive 'CCDC 256554' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C39 H24 O3' _chemical_formula_weight 540.58 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 Hexagonal _symmetry_space_group_name_H-M 'P6(3)/m ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' '-x, -y, z+1/2' 'y, -x+y, z+1/2' 'x-y, x, z+1/2' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' 'x, y, -z-1/2' '-y, x-y, -z-1/2' '-x+y, -x, -z-1/2' _cell_length_a 15.3580(4) _cell_length_b 15.3580(4) _cell_length_c 20.1237(12) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 4110.6(3) _cell_formula_units_Z 6 _cell_measurement_temperature 130(2) _cell_measurement_reflns_used 1721 _cell_measurement_theta_min 2.65 _cell_measurement_theta_max 27.00 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_min 0.10 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_max 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.310 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1692 _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 130(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 25909 _diffrn_reflns_av_R_equivalents 0.0977 _diffrn_reflns_av_sigmaI/netI 0.0825 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.53 _diffrn_reflns_theta_max 27.50 _reflns_number_total 3233 _reflns_number_gt 1982 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0270P)^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 0.00032(13) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3233 _refine_ls_number_parameters 194 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0966 _refine_ls_R_factor_gt 0.0497 _refine_ls_wR_factor_ref 0.0881 _refine_ls_wR_factor_gt 0.0773 _refine_ls_goodness_of_fit_ref 0.887 _refine_ls_restrained_S_all 0.887 _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 C1 C 0.01715(12) 0.77650(13) 0.39177(8) 0.0232(4) Uani 1 1 d . . . H1 H -0.0171 0.7150 0.4156 0.028 Uiso 1 1 calc R . . C1A C 0.00882(12) 0.77598(12) 0.32201(8) 0.0187(4) Uani 1 1 d . . . C2 C 0.07408(13) 0.86465(13) 0.42562(9) 0.0287(4) Uani 1 1 d . . . H2 H 0.0801 0.8640 0.4726 0.034 Uiso 1 1 calc R . . C3 C 0.12323(14) 0.95545(14) 0.39085(9) 0.0317(5) Uani 1 1 d . . . H3 H 0.1598 1.0169 0.4145 0.038 Uiso 1 1 calc R . . C4 C 0.11892(13) 0.95621(13) 0.32308(9) 0.0284(5) Uani 1 1 d . . . H4 H 0.1545 1.0185 0.3002 0.034 Uiso 1 1 calc R . . C4A C 0.06332(12) 0.86743(12) 0.28617(8) 0.0208(4) Uani 1 1 d . . . C10 C -0.05324(11) 0.68613(11) 0.28399(8) 0.0177(4) Uani 1 1 d . . . C11 C -0.12808(12) 0.58004(12) 0.30895(8) 0.0184(4) Uani 1 1 d . . . C12 C -0.20116(18) 0.55354(17) 0.2500 0.0210(6) Uani 1 2 d S . . C15 C -0.08505(12) 0.51082(12) 0.28902(7) 0.0194(4) Uani 1 1 d . . . H15 H -0.1352 0.4411 0.3036 0.023 Uiso 1 1 calc R . . C16 C 0.01417(13) 0.53674(12) 0.32094(9) 0.0244(4) Uani 1 1 d . . . C17 C 0.07781(12) 0.50492(12) 0.28439(8) 0.0269(4) Uani 1 1 d . . . C18 C 0.14241(14) 0.48153(14) 0.31922(11) 0.0380(5) Uani 1 1 d . . . H18 H 0.1441 0.4835 0.3664 0.046 Uiso 1 1 calc R . . C19 C 0.20342(15) 0.45565(15) 0.28469(10) 0.0487(6) Uani 1 1 d . . . H19 H 0.2458 0.4377 0.3082 0.058 Uiso 1 1 calc R . . C20 C -0.17933(12) 0.56565(12) 0.37510(8) 0.0226(4) Uani 1 1 d . . . C21 C -0.23356(13) 0.61489(13) 0.38622(9) 0.0290(5) Uani 1 1 d . . . H21 H -0.2359 0.6570 0.3525 0.035 Uiso 1 1 calc R . . C22 C -0.28417(14) 0.60355(14) 0.44553(10) 0.0380(5) Uani 1 1 d . . . H22 H -0.3204 0.6380 0.4524 0.046 Uiso 1 1 calc R . . C23 C -0.28167(15) 0.54197(15) 0.49461(10) 0.0428(6) Uani 1 1 d . . . H23 H -0.3155 0.5344 0.5356 0.051 Uiso 1 1 calc R . . C24 C -0.22987(15) 0.49179(14) 0.48379(9) 0.0406(6) Uani 1 1 d . . . H24 H -0.2286 0.4491 0.5175 0.049 Uiso 1 1 calc R . . C25 C -0.17932(14) 0.50242(13) 0.42442(9) 0.0293(5) Uani 1 1 d . . . H25 H -0.1447 0.4664 0.4176 0.035 Uiso 1 1 calc R . . O1 O -0.28994(13) 0.52128(14) 0.2500 0.0371(5) Uani 1 2 d S . . O2 O 0.03923(9) 0.57775(9) 0.37483(6) 0.0344(3) 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 0.0235(10) 0.0216(10) 0.0227(10) 0.0004(8) 0.0011(8) 0.0098(8) C1A 0.0161(9) 0.0192(9) 0.0215(10) -0.0022(8) 0.0000(8) 0.0094(8) C2 0.0302(11) 0.0275(11) 0.0240(11) -0.0046(9) -0.0019(9) 0.0110(10) C3 0.0354(12) 0.0226(11) 0.0294(12) -0.0102(9) -0.0058(9) 0.0087(9) C4 0.0319(11) 0.0177(10) 0.0298(12) -0.0012(8) -0.0006(9) 0.0079(9) C4A 0.0197(9) 0.0187(9) 0.0248(10) -0.0027(8) -0.0016(8) 0.0101(8) C10 0.0147(9) 0.0181(9) 0.0217(10) 0.0011(7) 0.0005(7) 0.0092(7) C11 0.0190(9) 0.0180(9) 0.0160(9) 0.0000(7) 0.0007(7) 0.0075(8) C12 0.0191(14) 0.0148(13) 0.0250(15) 0.000 0.000 0.0053(11) C15 0.0230(10) 0.0142(9) 0.0180(10) 0.0013(7) 0.0008(7) 0.0071(8) C16 0.0282(11) 0.0172(10) 0.0255(11) 0.0013(8) -0.0035(9) 0.0095(9) C17 0.0246(10) 0.0216(10) 0.0353(11) -0.0008(8) -0.0024(8) 0.0123(8) C18 0.0353(12) 0.0375(12) 0.0459(14) 0.0014(10) -0.0066(10) 0.0217(10) C19 0.0393(12) 0.0438(13) 0.0751(16) 0.0000(11) -0.0081(11) 0.0298(11) C20 0.0184(10) 0.0187(10) 0.0219(10) -0.0039(8) 0.0004(8) 0.0028(8) C21 0.0264(11) 0.0260(11) 0.0290(12) -0.0031(9) 0.0037(9) 0.0088(9) C22 0.0326(12) 0.0321(12) 0.0431(14) -0.0077(10) 0.0117(10) 0.0116(10) C23 0.0467(14) 0.0332(12) 0.0308(13) -0.0066(10) 0.0191(11) 0.0066(11) C24 0.0556(15) 0.0310(12) 0.0252(12) 0.0041(9) 0.0116(11) 0.0141(11) C25 0.0372(12) 0.0229(11) 0.0225(11) -0.0014(9) 0.0035(9) 0.0110(9) O1 0.0177(10) 0.0530(13) 0.0285(11) 0.000 0.000 0.0085(10) O2 0.0376(8) 0.0386(8) 0.0280(8) -0.0088(6) -0.0115(6) 0.0198(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.370(2) . ? C1 C1A 1.409(2) . ? C1 H1 0.9500 . ? C1A C4A 1.421(2) . ? C1A C10 1.443(2) . ? C2 C3 1.397(2) . ? C2 H2 0.9500 . ? C3 C4 1.366(2) . ? C3 H3 0.9500 . ? C4 C4A 1.406(2) . ? C4 H4 0.9500 . ? C4A C4A 1.456(3) 10_556 ? C10 C10 1.368(3) 10_556 ? C10 C11 1.535(2) . ? C11 C20 1.505(2) . ? C11 C12 1.541(2) . ? C11 C15 1.559(2) . ? C12 O1 1.195(3) . ? C12 C11 1.541(2) 10_556 ? C15 C16 1.512(2) . ? C15 C15 1.571(3) 10_556 ? C15 H15 1.0000 . ? C16 O2 1.2158(19) . ? C16 C17 1.488(2) . ? C17 C17 1.384(3) 10_556 ? C17 C18 1.400(2) . ? C18 C19 1.375(3) . ? C18 H18 0.9500 . ? C19 C19 1.396(4) 10_556 ? C19 H19 0.9500 . ? C20 C25 1.389(2) . ? C20 C21 1.395(2) . ? C21 C22 1.387(2) . ? C21 H21 0.9500 . ? C22 C23 1.381(3) . ? C22 H22 0.9500 . ? C23 C24 1.374(3) . ? C23 H23 0.9500 . ? C24 C25 1.389(2) . ? C24 H24 0.9500 . ? C25 H25 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 C2 C1 C1A 120.80(16) . . ? C2 C1 H1 119.6 . . ? C1A C1 H1 119.6 . . ? C1 C1A C4A 119.55(15) . . ? C1 C1A C10 123.25(15) . . ? C4A C1A C10 117.20(14) . . ? C1 C2 C3 119.79(17) . . ? C1 C2 H2 120.1 . . ? C3 C2 H2 120.1 . . ? C4 C3 C2 120.28(17) . . ? C4 C3 H3 119.9 . . ? C2 C3 H3 119.9 . . ? C3 C4 C4A 121.87(17) . . ? C3 C4 H4 119.1 . . ? C4A C4 H4 119.1 . . ? C4 C4A C1A 117.55(15) . . ? C4 C4A C4A 121.90(10) . 10_556 ? C1A C4A C4A 120.52(9) . 10_556 ? C10 C10 C1A 122.02(9) 10_556 . ? C10 C10 C11 109.11(8) 10_556 . ? C1A C10 C11 128.87(14) . . ? C20 C11 C10 120.29(13) . . ? C20 C11 C12 112.56(14) . . ? C10 C11 C12 95.07(13) . . ? C20 C11 C15 119.74(14) . . ? C10 C11 C15 106.98(12) . . ? C12 C11 C15 97.06(14) . . ? O1 C12 C11 129.68(9) . . ? O1 C12 C11 129.68(9) . 10_556 ? C11 C12 C11 100.65(18) . 10_556 ? C16 C15 C11 115.22(13) . . ? C16 C15 C15 115.14(9) . 10_556 ? C11 C15 C15 104.91(8) . 10_556 ? C16 C15 H15 107.0 . . ? C11 C15 H15 107.0 . . ? C15 C15 H15 107.0 10_556 . ? O2 C16 C17 121.41(16) . . ? O2 C16 C15 122.12(16) . . ? C17 C16 C15 116.40(15) . . ? C17 C17 C18 120.03(12) 10_556 . ? C17 C17 C16 119.63(10) 10_556 . ? C18 C17 C16 120.21(17) . . ? C19 C18 C17 119.59(19) . . ? C19 C18 H18 120.2 . . ? C17 C18 H18 120.2 . . ? C18 C19 C19 120.35(12) . 10_556 ? C18 C19 H19 119.8 . . ? C19 C19 H19 119.8 10_556 . ? C25 C20 C21 118.25(16) . . ? C25 C20 C11 123.49(16) . . ? C21 C20 C11 118.19(16) . . ? C22 C21 C20 121.27(18) . . ? C22 C21 H21 119.4 . . ? C20 C21 H21 119.4 . . ? C23 C22 C21 119.71(19) . . ? C23 C22 H22 120.1 . . ? C21 C22 H22 120.1 . . ? C24 C23 C22 119.54(19) . . ? C24 C23 H23 120.2 . . ? C22 C23 H23 120.2 . . ? C23 C24 C25 121.10(19) . . ? C23 C24 H24 119.4 . . ? C25 C24 H24 119.4 . . ? C20 C25 C24 120.10(18) . . ? C20 C25 H25 120.0 . . ? C24 C25 H25 120.0 . . ? 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 C2 C1 C1A C4A 2.5(3) . . . . ? C2 C1 C1A C10 -177.38(15) . . . . ? C1A C1 C2 C3 1.1(3) . . . . ? C1 C2 C3 C4 -3.3(3) . . . . ? C2 C3 C4 C4A 1.9(3) . . . . ? C3 C4 C4A C1A 1.7(3) . . . . ? C3 C4 C4A C4A -176.41(13) . . . 10_556 ? C1 C1A C4A C4 -3.8(2) . . . . ? C10 C1A C4A C4 176.07(15) . . . . ? C1 C1A C4A C4A 174.27(11) . . . 10_556 ? C10 C1A C4A C4A -5.82(17) . . . 10_556 ? C1 C1A C10 C10 -174.18(12) . . . 10_556 ? C4A C1A C10 C10 5.91(17) . . . 10_556 ? C1 C1A C10 C11 6.9(3) . . . . ? C4A C1A C10 C11 -172.97(15) . . . . ? C10 C10 C11 C20 -151.81(12) 10_556 . . . ? C1A C10 C11 C20 27.2(2) . . . . ? C10 C10 C11 C12 -31.96(12) 10_556 . . . ? C1A C10 C11 C12 147.04(17) . . . . ? C10 C10 C11 C15 67.02(11) 10_556 . . . ? C1A C10 C11 C15 -113.98(17) . . . . ? C20 C11 C12 O1 -2.7(3) . . . . ? C10 C11 C12 O1 -128.5(3) . . . . ? C15 C11 C12 O1 123.7(3) . . . . ? C20 C11 C12 C11 177.38(10) . . . 10_556 ? C10 C11 C12 C11 51.57(17) . . . 10_556 ? C15 C11 C12 C11 -56.27(17) . . . 10_556 ? C20 C11 C15 C16 -77.93(19) . . . . ? C10 C11 C15 C16 63.49(17) . . . . ? C12 C11 C15 C16 161.01(14) . . . . ? C20 C11 C15 C15 154.39(12) . . . 10_556 ? C10 C11 C15 C15 -64.19(11) . . . 10_556 ? C12 C11 C15 C15 33.33(11) . . . 10_556 ? C11 C15 C16 O2 28.0(2) . . . . ? C15 C15 C16 O2 150.31(13) 10_556 . . . ? C11 C15 C16 C17 -154.93(14) . . . . ? C15 C15 C16 C17 -32.58(16) 10_556 . . . ? O2 C16 C17 C17 -148.75(13) . . . 10_556 ? C15 C16 C17 C17 34.11(16) . . . 10_556 ? O2 C16 C17 C18 27.0(3) . . . . ? C15 C16 C17 C18 -150.14(16) . . . . ? C17 C17 C18 C19 -2.0(2) 10_556 . . . ? C16 C17 C18 C19 -177.71(17) . . . . ? C17 C18 C19 C19 2.0(2) . . . 10_556 ? C10 C11 C20 C25 -127.28(17) . . . . ? C12 C11 C20 C25 122.03(19) . . . . ? C15 C11 C20 C25 9.0(2) . . . . ? C10 C11 C20 C21 55.8(2) . . . . ? C12 C11 C20 C21 -54.9(2) . . . . ? C15 C11 C20 C21 -167.90(15) . . . . ? C25 C20 C21 C22 1.7(3) . . . . ? C11 C20 C21 C22 178.80(16) . . . . ? C20 C21 C22 C23 -0.4(3) . . . . ? C21 C22 C23 C24 -0.7(3) . . . . ? C22 C23 C24 C25 0.4(3) . . . . ? C21 C20 C25 C24 -1.9(3) . . . . ? C11 C20 C25 C24 -178.87(16) . . . . ? C23 C24 C25 C20 0.9(3) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.243 _refine_diff_density_min -0.213 _refine_diff_density_rms 0.041 data_jmwrg68 _database_code_depnum_ccdc_archive 'CCDC 256555' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C38 H26.50 N1.50 O' _chemical_formula_weight 520.11 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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'C2/c ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 20.7668(18) _cell_length_b 10.7728(8) _cell_length_c 25.1640(18) _cell_angle_alpha 90.00 _cell_angle_beta 104.376(2) _cell_angle_gamma 90.00 _cell_volume 5453.3(7) _cell_formula_units_Z 8 _cell_measurement_temperature 130(2) _cell_measurement_reflns_used 7638 _cell_measurement_theta_min 2.21 _cell_measurement_theta_max 27.46 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_min 0.30 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_max 0.50 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.267 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2184 _exptl_absorpt_coefficient_mu 0.076 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 130(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source '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 14041 _diffrn_reflns_av_R_equivalents 0.0945 _diffrn_reflns_av_sigmaI/netI 0.0597 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 1.67 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4789 _reflns_number_gt 4195 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _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^)+(0.0807P)^2^+0.9702P] 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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4789 _refine_ls_number_parameters 369 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0526 _refine_ls_R_factor_gt 0.0481 _refine_ls_wR_factor_ref 0.1369 _refine_ls_wR_factor_gt 0.1329 _refine_ls_goodness_of_fit_ref 1.072 _refine_ls_restrained_S_all 1.072 _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 C1 C 0.13779(8) 0.27449(13) -0.01091(6) 0.0250(3) Uani 1 1 d . . . H1 H 0.1722 0.3104 0.0170 0.030 Uiso 1 1 calc R . . C1A C 0.07563(7) 0.24932(13) 0.00002(5) 0.0220(3) Uani 1 1 d . . . C2 C 0.14955(8) 0.24809(14) -0.06102(6) 0.0291(4) Uani 1 1 d . . . H2 H 0.1920 0.2645 -0.0674 0.035 Uiso 1 1 calc R . . C3 C 0.09898(8) 0.19696(15) -0.10290(6) 0.0309(4) Uani 1 1 d . . . H3 H 0.1063 0.1832 -0.1382 0.037 Uiso 1 1 calc R . . C4 C 0.03907(8) 0.16684(14) -0.09280(6) 0.0276(3) Uani 1 1 d . . . H4 H 0.0057 0.1300 -0.1212 0.033 Uiso 1 1 calc R . . C4A C 0.02531(7) 0.18907(13) -0.04115(5) 0.0227(3) Uani 1 1 d . . . C5 C -0.08316(7) 0.07295(14) -0.06553(6) 0.0254(3) Uani 1 1 d . . . H5 H -0.0760 0.0536 -0.1004 0.030 Uiso 1 1 calc R . . C5A C -0.03604(7) 0.14689(13) -0.02870(5) 0.0220(3) Uani 1 1 d . . . C6 C -0.13898(7) 0.02846(13) -0.05208(6) 0.0269(3) Uani 1 1 d . . . H6 H -0.1704 -0.0189 -0.0781 0.032 Uiso 1 1 calc R . . C7 C -0.14997(7) 0.05233(13) -0.00038(6) 0.0253(3) Uani 1 1 d . . . H7 H -0.1883 0.0200 0.0090 0.030 Uiso 1 1 calc R . . C8 C -0.10507(7) 0.12277(13) 0.03679(5) 0.0218(3) Uani 1 1 d . . . H8 H -0.1122 0.1376 0.0721 0.026 Uiso 1 1 calc R . . C8A C -0.04848(7) 0.17352(12) 0.02329(5) 0.0205(3) Uani 1 1 d . . . C9 C -0.00013(7) 0.24683(12) 0.06108(5) 0.0200(3) Uani 1 1 d . . . C10 C 0.05933(7) 0.27928(12) 0.05087(5) 0.0206(3) Uani 1 1 d . . . C11 C 0.10372(7) 0.33919(13) 0.10356(5) 0.0209(3) Uani 1 1 d . . . C12 C 0.04476(7) 0.40148(13) 0.12142(5) 0.0207(3) Uani 1 1 d . . . C13 C -0.00083(7) 0.28579(13) 0.12000(5) 0.0206(3) Uani 1 1 d . . . C14 C 0.11478(7) 0.23435(13) 0.14673(5) 0.0207(3) Uani 1 1 d . . . C15 C 0.17132(7) 0.16776(13) 0.17181(5) 0.0225(3) Uani 1 1 d . . . H15 H 0.2130 0.1868 0.1645 0.027 Uiso 1 1 calc R . . C16 C 0.16588(7) 0.07199(13) 0.20802(6) 0.0246(3) Uani 1 1 d . . . H16 H 0.2045 0.0277 0.2265 0.030 Uiso 1 1 calc R . . C17 C 0.10481(7) 0.04084(13) 0.21735(6) 0.0250(3) Uani 1 1 d . . . H17 H 0.1021 -0.0248 0.2420 0.030 Uiso 1 1 calc R . . C18 C 0.04713(7) 0.10476(12) 0.19100(5) 0.0219(3) Uani 1 1 d . . . H18 H 0.0051 0.0816 0.1964 0.026 Uiso 1 1 calc R . . C19 C 0.05273(7) 0.20320(13) 0.15660(5) 0.0203(3) Uani 1 1 d . . . C20 C 0.15659(7) 0.43175(13) 0.09937(5) 0.0215(3) Uani 1 1 d . . . C21 C 0.22022(7) 0.43460(14) 0.13416(6) 0.0281(3) Uani 1 1 d . . . H21 H 0.2332 0.3727 0.1616 0.034 Uiso 1 1 calc R . . C22 C 0.26512(8) 0.52723(15) 0.12907(7) 0.0322(4) Uani 1 1 d . . . H22 H 0.3087 0.5268 0.1525 0.039 Uiso 1 1 calc R . . C23 C 0.24675(8) 0.61972(14) 0.09019(6) 0.0294(4) Uani 1 1 d . . . H23 H 0.2775 0.6827 0.0869 0.035 Uiso 1 1 calc R . . C24 C 0.18309(8) 0.61993(14) 0.05597(6) 0.0275(3) Uani 1 1 d . . . H24 H 0.1701 0.6837 0.0294 0.033 Uiso 1 1 calc R . . C25 C 0.13856(7) 0.52736(13) 0.06049(6) 0.0253(3) Uani 1 1 d . . . H25 H 0.0950 0.5284 0.0369 0.030 Uiso 1 1 calc R . . C26 C -0.06498(7) 0.32029(13) 0.13396(5) 0.0207(3) Uani 1 1 d . . . C27 C -0.10958(7) 0.39639(13) 0.09718(6) 0.0258(3) Uani 1 1 d . . . H27 H -0.1002 0.4187 0.0633 0.031 Uiso 1 1 calc R . . C28 C -0.16696(8) 0.43966(14) 0.10926(6) 0.0297(4) Uani 1 1 d . . . H28 H -0.1968 0.4906 0.0836 0.036 Uiso 1 1 calc R . . C29 C -0.18121(8) 0.40904(14) 0.15874(6) 0.0311(4) Uani 1 1 d . . . H29 H -0.2207 0.4386 0.1671 0.037 Uiso 1 1 calc R . . C30 C -0.13737(8) 0.33507(15) 0.19568(6) 0.0311(4) Uani 1 1 d . . . H30 H -0.1468 0.3137 0.2296 0.037 Uiso 1 1 calc R . . C31 C -0.07962(7) 0.29173(14) 0.18364(6) 0.0266(3) Uani 1 1 d . . . H31 H -0.0497 0.2419 0.2097 0.032 Uiso 1 1 calc R . . O1 O 0.03648(5) 0.50725(9) 0.13267(4) 0.0286(3) Uani 1 1 d . . . C34 C 0.0000 0.5977(2) 0.2500 0.0494(7) Uani 1 2 d S . . H34A H -0.0060 0.5674 0.2852 0.074 Uiso 0.50 1 calc PR . . H34B H 0.0424 0.5674 0.2446 0.074 Uiso 0.50 1 calc PR . . H34C H -0.0364 0.5674 0.2202 0.074 Uiso 0.50 1 calc PR . . C35 C 0.0000 0.7325(2) 0.2500 0.0318(5) Uani 1 2 d S . . N2 N 0.0000 0.8378(2) 0.2500 0.0448(5) Uani 1 2 d S . . C32 C 0.14743(11) 0.72454(17) 0.17916(7) 0.0455(5) Uani 1 1 d . . . H32A H 0.0995 0.7191 0.1628 0.068 Uiso 1 1 calc R . . H32B H 0.1697 0.6528 0.1677 0.068 Uiso 1 1 calc R . . H32C H 0.1648 0.8011 0.1669 0.068 Uiso 1 1 calc R . . C33 C 0.15965(7) 0.72545(15) 0.23831(7) 0.0309(4) Uani 1 1 d . . . N1 N 0.16868(7) 0.72724(16) 0.28497(6) 0.0485(4) 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 0.0314(8) 0.0195(7) 0.0258(8) 0.0002(6) 0.0103(6) 0.0004(6) C1A 0.0297(8) 0.0173(7) 0.0200(7) 0.0031(5) 0.0078(6) 0.0034(6) C2 0.0361(9) 0.0253(8) 0.0310(8) 0.0025(6) 0.0181(7) 0.0007(6) C3 0.0450(9) 0.0306(9) 0.0207(7) 0.0018(6) 0.0153(7) 0.0039(7) C4 0.0372(9) 0.0261(8) 0.0198(7) 0.0000(6) 0.0079(6) 0.0031(6) C4A 0.0317(8) 0.0178(7) 0.0183(7) 0.0022(5) 0.0057(6) 0.0044(6) C5 0.0336(8) 0.0234(8) 0.0180(7) -0.0021(5) 0.0043(6) 0.0038(6) C5A 0.0289(8) 0.0183(7) 0.0181(7) 0.0024(5) 0.0042(6) 0.0057(6) C6 0.0313(8) 0.0218(8) 0.0249(8) -0.0046(6) 0.0018(6) 0.0002(6) C7 0.0269(8) 0.0199(7) 0.0283(8) 0.0000(6) 0.0057(6) -0.0008(6) C8 0.0279(7) 0.0187(7) 0.0189(7) 0.0015(5) 0.0059(6) 0.0026(6) C8A 0.0272(8) 0.0149(7) 0.0186(7) 0.0015(5) 0.0040(6) 0.0040(5) C9 0.0269(8) 0.0172(7) 0.0163(7) 0.0021(5) 0.0058(6) 0.0026(6) C10 0.0275(7) 0.0155(7) 0.0178(7) 0.0023(5) 0.0039(6) 0.0013(6) C11 0.0267(8) 0.0197(7) 0.0164(7) 0.0005(5) 0.0055(6) -0.0001(6) C12 0.0267(7) 0.0210(8) 0.0134(6) 0.0013(5) 0.0032(5) -0.0004(6) C13 0.0266(7) 0.0191(7) 0.0158(7) -0.0005(5) 0.0044(5) -0.0017(6) C14 0.0300(8) 0.0173(7) 0.0151(6) -0.0033(5) 0.0060(6) -0.0019(6) C15 0.0273(8) 0.0202(7) 0.0197(7) -0.0033(5) 0.0054(6) -0.0006(6) C16 0.0323(8) 0.0195(7) 0.0203(7) -0.0012(5) 0.0032(6) 0.0039(6) C17 0.0391(9) 0.0174(7) 0.0186(7) 0.0004(5) 0.0074(6) 0.0011(6) C18 0.0320(8) 0.0180(7) 0.0171(7) -0.0032(5) 0.0090(6) -0.0026(6) C19 0.0275(7) 0.0192(7) 0.0139(6) -0.0039(5) 0.0045(5) 0.0006(6) C20 0.0280(7) 0.0184(7) 0.0196(7) -0.0023(5) 0.0087(6) -0.0002(6) C21 0.0314(8) 0.0229(8) 0.0279(8) 0.0017(6) 0.0034(6) -0.0014(6) C22 0.0259(8) 0.0293(9) 0.0391(9) -0.0011(7) 0.0040(7) -0.0034(6) C23 0.0331(8) 0.0231(8) 0.0351(8) -0.0030(6) 0.0141(7) -0.0072(6) C24 0.0380(9) 0.0214(8) 0.0249(7) 0.0020(6) 0.0111(6) -0.0017(6) C25 0.0298(8) 0.0238(8) 0.0220(7) 0.0000(6) 0.0057(6) -0.0020(6) C26 0.0270(7) 0.0170(7) 0.0187(7) -0.0036(5) 0.0067(5) -0.0039(6) C27 0.0334(8) 0.0229(8) 0.0227(7) 0.0015(6) 0.0098(6) 0.0000(6) C28 0.0318(8) 0.0235(8) 0.0340(8) 0.0039(6) 0.0087(7) 0.0042(6) C29 0.0307(8) 0.0266(8) 0.0399(9) -0.0032(7) 0.0162(7) 0.0011(6) C30 0.0377(9) 0.0326(9) 0.0276(8) 0.0012(6) 0.0169(7) 0.0003(7) C31 0.0310(8) 0.0273(8) 0.0219(7) 0.0021(6) 0.0076(6) 0.0010(6) O1 0.0359(6) 0.0192(6) 0.0329(6) -0.0041(4) 0.0124(5) -0.0011(4) C34 0.0684(18) 0.0313(14) 0.0606(17) 0.000 0.0387(15) 0.000 C35 0.0308(12) 0.0327(14) 0.0355(12) 0.000 0.0153(10) 0.000 N2 0.0367(12) 0.0365(13) 0.0629(15) 0.000 0.0151(10) 0.000 C32 0.0682(13) 0.0330(10) 0.0367(10) -0.0064(7) 0.0159(9) -0.0038(9) C33 0.0260(8) 0.0277(9) 0.0391(10) -0.0051(7) 0.0085(7) 0.0011(6) N1 0.0378(9) 0.0673(11) 0.0381(9) -0.0043(7) 0.0053(7) 0.0036(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.372(2) . ? C1 C1A 1.411(2) . ? C1 H1 0.9500 . ? C1A C4A 1.431(2) . ? C1A C10 1.4391(19) . ? C2 C3 1.403(2) . ? C2 H2 0.9500 . ? C3 C4 1.369(2) . ? C3 H3 0.9500 . ? C4 C4A 1.4187(19) . ? C4 H4 0.9500 . ? C4A C5A 1.458(2) . ? C5 C6 1.372(2) . ? C5 C5A 1.414(2) . ? C5 H5 0.9500 . ? C5A C8A 1.4242(18) . ? C6 C7 1.399(2) . ? C6 H6 0.9500 . ? C7 C8 1.374(2) . ? C7 H7 0.9500 . ? C8 C8A 1.4118(19) . ? C8 H8 0.9500 . ? C8A C9 1.4360(19) . ? C9 C10 1.368(2) . ? C9 C13 1.5446(18) . ? C10 C11 1.5547(18) . ? C11 C20 1.5059(19) . ? C11 C14 1.5443(18) . ? C11 C12 1.5572(19) . ? C12 O1 1.1968(16) . ? C12 C13 1.5602(19) . ? C13 C26 1.506(2) . ? C13 C19 1.5389(19) . ? C14 C15 1.387(2) . ? C14 C19 1.412(2) . ? C15 C16 1.399(2) . ? C15 H15 0.9500 . ? C16 C17 1.387(2) . ? C16 H16 0.9500 . ? C17 C18 1.398(2) . ? C17 H17 0.9500 . ? C18 C19 1.3918(19) . ? C18 H18 0.9500 . ? C20 C21 1.393(2) . ? C20 C25 1.406(2) . ? C21 C22 1.393(2) . ? C21 H21 0.9500 . ? C22 C23 1.382(2) . ? C22 H22 0.9500 . ? C23 C24 1.387(2) . ? C23 H23 0.9500 . ? C24 C25 1.384(2) . ? C24 H24 0.9500 . ? C25 H25 0.9500 . ? C26 C31 1.3922(19) . ? C26 C27 1.400(2) . ? C27 C28 1.382(2) . ? C27 H27 0.9500 . ? C28 C29 1.389(2) . ? C28 H28 0.9500 . ? C29 C30 1.381(2) . ? C29 H29 0.9500 . ? C30 C31 1.389(2) . ? C30 H30 0.9500 . ? C31 H31 0.9500 . ? C34 C35 1.452(3) . ? C34 H34A 0.9800 . ? C34 H34B 0.9800 . ? C34 H34C 0.9800 . ? C35 N2 1.134(3) . ? C32 C33 1.447(2) . ? C32 H32A 0.9800 . ? C32 H32B 0.9800 . ? C32 H32C 0.9800 . ? C33 N1 1.142(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C1A 121.28(14) . . ? C2 C1 H1 119.4 . . ? C1A C1 H1 119.4 . . ? C1 C1A C4A 118.99(13) . . ? C1 C1A C10 123.96(13) . . ? C4A C1A C10 117.05(13) . . ? C1 C2 C3 120.06(14) . . ? C1 C2 H2 120.0 . . ? C3 C2 H2 120.0 . . ? C4 C3 C2 119.94(13) . . ? C4 C3 H3 120.0 . . ? C2 C3 H3 120.0 . . ? C3 C4 C4A 121.94(14) . . ? C3 C4 H4 119.0 . . ? C4A C4 H4 119.0 . . ? C4 C4A C1A 117.56(13) . . ? C4 C4A C5A 121.99(13) . . ? C1A C4A C5A 120.37(12) . . ? C6 C5 C5A 121.63(13) . . ? C6 C5 H5 119.2 . . ? C5A C5 H5 119.2 . . ? C5 C5A C8A 117.48(13) . . ? C5 C5A C4A 122.28(12) . . ? C8A C5A C4A 120.14(12) . . ? C5 C6 C7 120.52(13) . . ? C5 C6 H6 119.7 . . ? C7 C6 H6 119.7 . . ? C8 C7 C6 119.65(14) . . ? C8 C7 H7 120.2 . . ? C6 C7 H7 120.2 . . ? C7 C8 C8A 120.99(13) . . ? C7 C8 H8 119.5 . . ? C8A C8 H8 119.5 . . ? C8 C8A C5A 119.65(12) . . ? C8 C8A C9 122.72(12) . . ? C5A C8A C9 117.55(12) . . ? C10 C9 C8A 122.12(12) . . ? C10 C9 C13 109.56(12) . . ? C8A C9 C13 127.84(12) . . ? C9 C10 C1A 122.15(13) . . ? C9 C10 C11 108.54(11) . . ? C1A C10 C11 129.11(13) . . ? C20 C11 C14 123.35(12) . . ? C20 C11 C10 120.23(11) . . ? C14 C11 C10 104.44(11) . . ? C20 C11 C12 111.96(11) . . ? C14 C11 C12 95.88(10) . . ? C10 C11 C12 94.75(10) . . ? O1 C12 C11 130.40(12) . . ? O1 C12 C13 130.08(13) . . ? C11 C12 C13 99.52(11) . . ? C26 C13 C19 123.55(11) . . ? C26 C13 C9 120.70(11) . . ? C19 C13 C9 103.88(11) . . ? C26 C13 C12 111.37(11) . . ? C19 C13 C12 95.97(10) . . ? C9 C13 C12 95.09(10) . . ? C15 C14 C19 120.23(13) . . ? C15 C14 C11 131.28(13) . . ? C19 C14 C11 108.34(12) . . ? C14 C15 C16 118.78(13) . . ? C14 C15 H15 120.6 . . ? C16 C15 H15 120.6 . . ? C17 C16 C15 120.91(13) . . ? C17 C16 H16 119.5 . . ? C15 C16 H16 119.5 . . ? C16 C17 C18 120.81(13) . . ? C16 C17 H17 119.6 . . ? C18 C17 H17 119.6 . . ? C19 C18 C17 118.45(13) . . ? C19 C18 H18 120.8 . . ? C17 C18 H18 120.8 . . ? C18 C19 C14 120.74(13) . . ? C18 C19 C13 130.79(13) . . ? C14 C19 C13 108.23(11) . . ? C21 C20 C25 117.93(13) . . ? C21 C20 C11 124.41(13) . . ? C25 C20 C11 117.45(12) . . ? C20 C21 C22 120.69(14) . . ? C20 C21 H21 119.7 . . ? C22 C21 H21 119.7 . . ? C23 C22 C21 120.53(14) . . ? C23 C22 H22 119.7 . . ? C21 C22 H22 119.7 . . ? C22 C23 C24 119.58(14) . . ? C22 C23 H23 120.2 . . ? C24 C23 H23 120.2 . . ? C25 C24 C23 120.08(14) . . ? C25 C24 H24 120.0 . . ? C23 C24 H24 120.0 . . ? C24 C25 C20 121.15(14) . . ? C24 C25 H25 119.4 . . ? C20 C25 H25 119.4 . . ? C31 C26 C27 117.83(13) . . ? C31 C26 C13 123.91(13) . . ? C27 C26 C13 117.93(12) . . ? C28 C27 C26 121.13(13) . . ? C28 C27 H27 119.4 . . ? C26 C27 H27 119.4 . . ? C27 C28 C29 120.29(14) . . ? C27 C28 H28 119.9 . . ? C29 C28 H28 119.9 . . ? C30 C29 C28 119.26(14) . . ? C30 C29 H29 120.4 . . ? C28 C29 H29 120.4 . . ? C29 C30 C31 120.51(14) . . ? C29 C30 H30 119.7 . . ? C31 C30 H30 119.7 . . ? C30 C31 C26 120.97(14) . . ? C30 C31 H31 119.5 . . ? C26 C31 H31 119.5 . . ? C35 C34 H34A 109.5 . . ? C35 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? C35 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? N2 C35 C34 180.000(1) . . ? C33 C32 H32A 109.5 . . ? C33 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C33 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? N1 C33 C32 179.15(19) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C2 C1 C1A C4A 3.3(2) . . . . ? C2 C1 C1A C10 -177.43(13) . . . . ? C1A C1 C2 C3 1.1(2) . . . . ? C1 C2 C3 C4 -3.7(2) . . . . ? C2 C3 C4 C4A 1.9(2) . . . . ? C3 C4 C4A C1A 2.5(2) . . . . ? C3 C4 C4A C5A -174.29(13) . . . . ? C1 C1A C4A C4 -5.0(2) . . . . ? C10 C1A C4A C4 175.72(12) . . . . ? C1 C1A C4A C5A 171.81(12) . . . . ? C10 C1A C4A C5A -7.46(19) . . . . ? C6 C5 C5A C8A 0.2(2) . . . . ? C6 C5 C5A C4A 176.51(13) . . . . ? C4 C4A C5A C5 5.1(2) . . . . ? C1A C4A C5A C5 -171.55(13) . . . . ? C4 C4A C5A C8A -178.66(12) . . . . ? C1A C4A C5A C8A 4.7(2) . . . . ? C5A C5 C6 C7 -1.9(2) . . . . ? C5 C6 C7 C8 1.2(2) . . . . ? C6 C7 C8 C8A 1.2(2) . . . . ? C7 C8 C8A C5A -2.8(2) . . . . ? C7 C8 C8A C9 -179.52(13) . . . . ? C5 C5A C8A C8 2.12(19) . . . . ? C4A C5A C8A C8 -174.28(12) . . . . ? C5 C5A C8A C9 178.98(12) . . . . ? C4A C5A C8A C9 2.58(19) . . . . ? C8 C8A C9 C10 169.66(13) . . . . ? C5A C8A C9 C10 -7.1(2) . . . . ? C8 C8A C9 C13 -1.6(2) . . . . ? C5A C8A C9 C13 -178.39(12) . . . . ? C8A C9 C10 C1A 4.3(2) . . . . ? C13 C9 C10 C1A 176.98(12) . . . . ? C8A C9 C10 C11 -170.98(12) . . . . ? C13 C9 C10 C11 1.73(15) . . . . ? C1 C1A C10 C9 -176.09(13) . . . . ? C4A C1A C10 C9 3.1(2) . . . . ? C1 C1A C10 C11 -1.9(2) . . . . ? C4A C1A C10 C11 177.34(13) . . . . ? C9 C10 C11 C20 -153.04(12) . . . . ? C1A C10 C11 C20 32.1(2) . . . . ? C9 C10 C11 C14 63.15(14) . . . . ? C1A C10 C11 C14 -111.67(15) . . . . ? C9 C10 C11 C12 -34.18(13) . . . . ? C1A C10 C11 C12 151.01(14) . . . . ? C20 C11 C12 O1 -1.40(19) . . . . ? C14 C11 C12 O1 128.21(15) . . . . ? C10 C11 C12 O1 -126.72(15) . . . . ? C20 C11 C12 C13 178.23(10) . . . . ? C14 C11 C12 C13 -52.17(11) . . . . ? C10 C11 C12 C13 52.90(10) . . . . ? C10 C9 C13 C26 150.03(13) . . . . ? C8A C9 C13 C26 -37.8(2) . . . . ? C10 C9 C13 C19 -65.99(14) . . . . ? C8A C9 C13 C19 106.19(15) . . . . ? C10 C9 C13 C12 31.45(14) . . . . ? C8A C9 C13 C12 -156.37(13) . . . . ? O1 C12 C13 C26 1.76(19) . . . . ? C11 C12 C13 C26 -177.86(10) . . . . ? O1 C12 C13 C19 -127.85(15) . . . . ? C11 C12 C13 C19 52.53(11) . . . . ? O1 C12 C13 C9 127.58(15) . . . . ? C11 C12 C13 C9 -52.04(11) . . . . ? C20 C11 C14 C15 -31.0(2) . . . . ? C10 C11 C14 C15 111.31(16) . . . . ? C12 C11 C14 C15 -152.23(14) . . . . ? C20 C11 C14 C19 153.50(12) . . . . ? C10 C11 C14 C19 -64.14(13) . . . . ? C12 C11 C14 C19 32.32(13) . . . . ? C19 C14 C15 C16 -1.74(19) . . . . ? C11 C14 C15 C16 -176.74(13) . . . . ? C14 C15 C16 C17 2.3(2) . . . . ? C15 C16 C17 C18 -0.3(2) . . . . ? C16 C17 C18 C19 -2.2(2) . . . . ? C17 C18 C19 C14 2.67(19) . . . . ? C17 C18 C19 C13 176.28(13) . . . . ? C15 C14 C19 C18 -0.74(19) . . . . ? C11 C14 C19 C18 175.31(11) . . . . ? C15 C14 C19 C13 -175.65(11) . . . . ? C11 C14 C19 C13 0.40(14) . . . . ? C26 C13 C19 C18 32.3(2) . . . . ? C9 C13 C19 C18 -110.33(16) . . . . ? C12 C13 C19 C18 152.91(14) . . . . ? C26 C13 C19 C14 -153.47(12) . . . . ? C9 C13 C19 C14 63.89(13) . . . . ? C12 C13 C19 C14 -32.87(13) . . . . ? C14 C11 C20 C21 -1.2(2) . . . . ? C10 C11 C20 C21 -138.02(14) . . . . ? C12 C11 C20 C21 112.21(15) . . . . ? C14 C11 C20 C25 -175.94(12) . . . . ? C10 C11 C20 C25 47.26(18) . . . . ? C12 C11 C20 C25 -62.51(15) . . . . ? C25 C20 C21 C22 -2.2(2) . . . . ? C11 C20 C21 C22 -176.87(14) . . . . ? C20 C21 C22 C23 1.5(2) . . . . ? C21 C22 C23 C24 -0.1(2) . . . . ? C22 C23 C24 C25 -0.6(2) . . . . ? C23 C24 C25 C20 -0.1(2) . . . . ? C21 C20 C25 C24 1.5(2) . . . . ? C11 C20 C25 C24 176.57(13) . . . . ? C19 C13 C26 C31 6.7(2) . . . . ? C9 C13 C26 C31 143.45(14) . . . . ? C12 C13 C26 C31 -106.48(15) . . . . ? C19 C13 C26 C27 179.88(12) . . . . ? C9 C13 C26 C27 -43.36(18) . . . . ? C12 C13 C26 C27 66.72(15) . . . . ? C31 C26 C27 C28 -1.3(2) . . . . ? C13 C26 C27 C28 -174.94(13) . . . . ? C26 C27 C28 C29 0.6(2) . . . . ? C27 C28 C29 C30 0.1(2) . . . . ? C28 C29 C30 C31 0.1(2) . . . . ? C29 C30 C31 C26 -0.8(2) . . . . ? C27 C26 C31 C30 1.5(2) . . . . ? C13 C26 C31 C30 174.66(13) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.301 _refine_diff_density_min -0.233 _refine_diff_density_rms 0.050 data_jmwrg61 _database_code_depnum_ccdc_archive 'CCDC 256556' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C35 H22 O3' _chemical_formula_weight 490.53 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 Triclinic _symmetry_space_group_name_H-M 'P-1 ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.0236(11) _cell_length_b 10.4368(11) _cell_length_c 12.1152(13) _cell_angle_alpha 109.755(2) _cell_angle_beta 103.475(2) _cell_angle_gamma 90.167(2) _cell_volume 1155.4(2) _cell_formula_units_Z 2 _cell_measurement_temperature 130(2) _cell_measurement_reflns_used 1117 _cell_measurement_theta_min 2.25 _cell_measurement_theta_max 27.03 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_min 0.10 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_max 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.410 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 512 _exptl_absorpt_coefficient_mu 0.089 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 130(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_source '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 6182 _diffrn_reflns_av_R_equivalents 0.0390 _diffrn_reflns_av_sigmaI/netI 0.1008 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.84 _diffrn_reflns_theta_max 24.99 _reflns_number_total 4034 _reflns_number_gt 2534 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _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^)+(0.0136P)^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 0.0035(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4034 _refine_ls_number_parameters 344 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0788 _refine_ls_R_factor_gt 0.0456 _refine_ls_wR_factor_ref 0.0753 _refine_ls_wR_factor_gt 0.0676 _refine_ls_goodness_of_fit_ref 0.803 _refine_ls_restrained_S_all 0.803 _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 C1 C 0.9098(2) 0.6945(2) 0.31402(19) 0.0268(6) Uani 1 1 d . . . H1 H 0.9701 0.6809 0.2619 0.032 Uiso 1 1 calc R . . C1A C 0.8381(2) 0.8109(2) 0.33502(18) 0.0201(5) Uani 1 1 d . . . C2 C 0.8958(2) 0.5981(2) 0.3669(2) 0.0301(6) Uani 1 1 d . . . H2 H 0.9464 0.5198 0.3521 0.036 Uiso 1 1 calc R . . C3 C 0.8069(2) 0.6184(2) 0.4413(2) 0.0313(6) Uani 1 1 d . . . H3 H 0.7916 0.5509 0.4746 0.038 Uiso 1 1 calc R . . C4 C 0.7399(2) 0.7364(2) 0.46786(19) 0.0278(6) Uani 1 1 d . . . H4 H 0.6797 0.7489 0.5200 0.033 Uiso 1 1 calc R . . C4A C 0.7586(2) 0.8380(2) 0.41983(18) 0.0206(5) Uani 1 1 d . . . C5 C 0.6581(2) 1.0133(2) 0.57056(18) 0.0251(6) Uani 1 1 d . . . H5 H 0.6412 0.9455 0.6030 0.030 Uiso 1 1 calc R . . C5A C 0.7103(2) 0.9761(2) 0.46698(18) 0.0205(5) Uani 1 1 d . . . C6 C 0.6309(2) 1.1460(2) 0.62620(19) 0.0286(6) Uani 1 1 d . . . H6 H 0.5940 1.1680 0.6952 0.034 Uiso 1 1 calc R . . C7 C 0.6569(2) 1.2467(2) 0.58244(19) 0.0298(6) Uani 1 1 d . . . H7 H 0.6408 1.3387 0.6220 0.036 Uiso 1 1 calc R . . C8 C 0.7069(2) 1.2117(2) 0.47978(19) 0.0275(6) Uani 1 1 d . . . H8 H 0.7248 1.2809 0.4491 0.033 Uiso 1 1 calc R . . C8A C 0.7317(2) 1.0782(2) 0.42050(18) 0.0209(5) Uani 1 1 d . . . C9 C 0.7869(2) 1.0461(2) 0.31039(18) 0.0206(5) Uani 1 1 d . . . C10 C 0.8459(2) 0.9038(2) 0.26623(18) 0.0193(5) Uani 1 1 d . . . C11 C 0.7752(2) 0.8432(2) 0.12326(18) 0.0204(5) Uani 1 1 d . . . C12 C 0.6371(2) 0.9060(2) 0.12228(18) 0.0206(5) Uani 1 1 d . . . C13 C 0.6855(2) 1.0570(2) 0.19117(18) 0.0213(5) Uani 1 1 d . . . C14 C 0.7917(2) 1.0812(2) 0.12451(19) 0.0243(6) Uani 1 1 d . . . H14 H 0.7521 1.1166 0.0578 0.029 Uiso 1 1 calc R . . C15 C 0.8524(2) 0.9369(2) 0.07924(19) 0.0228(6) Uani 1 1 d . . . H15 H 0.8426 0.9006 -0.0102 0.027 Uiso 1 1 calc R . . C16 C 1.0002(2) 0.9464(2) 0.1524(2) 0.0257(6) Uani 1 1 d . . . C17 C 0.9880(2) 0.9764(2) 0.28001(18) 0.0238(6) Uani 1 1 d . . . H17 H 1.0687 0.9588 0.3376 0.029 Uiso 1 1 calc R . . C18 C 0.9285(2) 1.1201(2) 0.32487(19) 0.0248(6) Uani 1 1 d . . . H18 H 0.9755 1.1840 0.4078 0.030 Uiso 1 1 calc R . . C19 C 0.9064(2) 1.1771(2) 0.2235(2) 0.0267(6) Uani 1 1 d . . . C20 C 0.7711(2) 0.6923(2) 0.05766(18) 0.0223(5) Uani 1 1 d . . . C21 C 0.8541(2) 0.6388(2) -0.02128(18) 0.0283(6) Uani 1 1 d . . . H21 H 0.9158 0.6987 -0.0339 0.034 Uiso 1 1 calc R . . C22 C 0.8480(2) 0.4997(3) -0.0816(2) 0.0360(7) Uani 1 1 d . . . H22 H 0.9047 0.4652 -0.1360 0.043 Uiso 1 1 calc R . . C23 C 0.7607(2) 0.4102(3) -0.0638(2) 0.0370(7) Uani 1 1 d . . . H23 H 0.7578 0.3145 -0.1046 0.044 Uiso 1 1 calc R . . C24 C 0.6775(2) 0.4621(2) 0.0146(2) 0.0318(6) Uani 1 1 d . . . H24 H 0.6167 0.4016 0.0274 0.038 Uiso 1 1 calc R . . C25 C 0.6821(2) 0.6011(2) 0.07428(19) 0.0259(6) Uani 1 1 d . . . H25 H 0.6239 0.6352 0.1274 0.031 Uiso 1 1 calc R . . C26 C 0.5784(2) 1.1583(2) 0.20870(18) 0.0213(5) Uani 1 1 d . . . C27 C 0.4496(2) 1.1202(2) 0.21918(18) 0.0255(6) Uani 1 1 d . . . H27 H 0.4272 1.0282 0.2103 0.031 Uiso 1 1 calc R . . C28 C 0.3539(2) 1.2153(2) 0.24237(18) 0.0265(6) Uani 1 1 d . . . H28 H 0.2664 1.1880 0.2489 0.032 Uiso 1 1 calc R . . C29 C 0.3856(2) 1.3489(2) 0.25596(19) 0.0318(6) Uani 1 1 d . . . H29 H 0.3206 1.4142 0.2733 0.038 Uiso 1 1 calc R . . C30 C 0.5118(2) 1.3883(2) 0.2445(2) 0.0330(6) Uani 1 1 d . . . H30 H 0.5337 1.4804 0.2535 0.040 Uiso 1 1 calc R . . C31 C 0.6065(2) 1.2926(2) 0.21976(19) 0.0278(6) Uani 1 1 d . . . H31 H 0.6924 1.3199 0.2102 0.033 Uiso 1 1 calc R . . O1 O 0.52257(15) 0.84924(15) 0.07866(13) 0.0292(4) Uani 1 1 d . . . O2 O 1.10344(15) 0.93238(16) 0.11559(13) 0.0332(4) Uani 1 1 d . . . O3 O 0.97024(16) 1.27451(16) 0.22052(14) 0.0350(4) 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 0.0259(14) 0.0296(15) 0.0232(13) 0.0068(12) 0.0067(10) 0.0031(12) C1A 0.0192(12) 0.0208(14) 0.0159(12) 0.0029(11) 0.0013(10) -0.0008(11) C2 0.0348(15) 0.0249(15) 0.0278(14) 0.0089(12) 0.0028(11) 0.0060(12) C3 0.0383(16) 0.0231(15) 0.0303(15) 0.0113(12) 0.0015(12) -0.0048(12) C4 0.0275(14) 0.0283(15) 0.0275(14) 0.0092(12) 0.0072(11) -0.0017(12) C4A 0.0157(12) 0.0234(14) 0.0197(12) 0.0068(11) -0.0002(10) -0.0010(10) C5 0.0208(13) 0.0308(16) 0.0229(13) 0.0091(12) 0.0044(10) 0.0009(11) C5A 0.0125(12) 0.0262(14) 0.0176(12) 0.0044(11) -0.0010(9) -0.0009(10) C6 0.0234(14) 0.0392(17) 0.0195(13) 0.0041(12) 0.0077(10) 0.0044(12) C7 0.0318(15) 0.0259(15) 0.0253(14) 0.0004(12) 0.0079(11) 0.0048(12) C8 0.0303(14) 0.0274(15) 0.0234(13) 0.0086(12) 0.0046(11) 0.0029(12) C8A 0.0157(12) 0.0236(14) 0.0206(12) 0.0054(11) 0.0026(10) 0.0025(11) C9 0.0205(12) 0.0192(13) 0.0193(12) 0.0039(11) 0.0037(10) -0.0003(10) C10 0.0212(13) 0.0199(13) 0.0153(12) 0.0040(10) 0.0048(9) 0.0009(10) C11 0.0199(13) 0.0228(14) 0.0180(12) 0.0060(11) 0.0051(10) 0.0009(11) C12 0.0226(13) 0.0268(15) 0.0135(12) 0.0081(11) 0.0054(10) 0.0009(11) C13 0.0229(13) 0.0218(14) 0.0209(12) 0.0089(11) 0.0061(10) 0.0018(11) C14 0.0255(13) 0.0254(14) 0.0256(13) 0.0125(12) 0.0077(10) 0.0020(11) C15 0.0247(13) 0.0264(14) 0.0176(12) 0.0067(11) 0.0072(10) 0.0019(11) C16 0.0272(14) 0.0201(14) 0.0320(14) 0.0094(12) 0.0112(11) -0.0010(11) C17 0.0187(12) 0.0293(15) 0.0207(12) 0.0063(11) 0.0037(10) 0.0001(11) C18 0.0251(13) 0.0223(14) 0.0232(13) 0.0040(11) 0.0048(10) -0.0020(11) C19 0.0261(14) 0.0247(15) 0.0307(14) 0.0062(12) 0.0149(11) 0.0026(12) C20 0.0224(13) 0.0242(14) 0.0168(12) 0.0054(11) 0.0009(10) 0.0025(11) C21 0.0286(14) 0.0292(16) 0.0222(13) 0.0043(12) 0.0038(11) 0.0031(12) C22 0.0339(16) 0.0417(18) 0.0238(14) 0.0035(13) 0.0029(11) 0.0160(14) C23 0.0420(17) 0.0250(16) 0.0302(15) 0.0006(13) -0.0035(12) 0.0094(14) C24 0.0314(15) 0.0250(16) 0.0338(15) 0.0105(13) -0.0022(12) 0.0007(12) C25 0.0261(14) 0.0265(15) 0.0212(13) 0.0052(11) 0.0030(10) 0.0023(12) C26 0.0252(13) 0.0224(14) 0.0156(12) 0.0071(11) 0.0030(10) 0.0001(11) C27 0.0333(14) 0.0218(14) 0.0223(13) 0.0082(11) 0.0078(11) 0.0022(12) C28 0.0262(14) 0.0291(15) 0.0232(13) 0.0084(12) 0.0051(10) 0.0037(12) C29 0.0346(16) 0.0296(16) 0.0267(14) 0.0077(12) 0.0025(11) 0.0103(13) C30 0.0391(16) 0.0227(15) 0.0361(15) 0.0121(12) 0.0046(12) 0.0044(13) C31 0.0270(14) 0.0266(15) 0.0322(14) 0.0142(12) 0.0058(11) 0.0015(12) O1 0.0228(9) 0.0279(10) 0.0320(9) 0.0052(8) 0.0053(7) 0.0004(8) O2 0.0285(10) 0.0399(11) 0.0364(10) 0.0143(9) 0.0165(8) 0.0036(8) O3 0.0368(11) 0.0284(11) 0.0434(11) 0.0141(9) 0.0147(8) -0.0054(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.385(3) . ? C1 C1A 1.392(3) . ? C1 H1 0.9500 . ? C1A C4A 1.398(3) . ? C1A C10 1.489(3) . ? C2 C3 1.379(3) . ? C2 H2 0.9500 . ? C3 C4 1.381(3) . ? C3 H3 0.9500 . ? C4 C4A 1.402(3) . ? C4 H4 0.9500 . ? C4A C5A 1.488(3) . ? C5 C6 1.380(3) . ? C5 C5A 1.406(3) . ? C5 H5 0.9500 . ? C5A C8A 1.400(3) . ? C6 C7 1.376(3) . ? C6 H6 0.9500 . ? C7 C8 1.384(3) . ? C7 H7 0.9500 . ? C8 C8A 1.389(3) . ? C8 H8 0.9500 . ? C8A C9 1.497(3) . ? C9 C18 1.558(3) . ? C9 C10 1.567(3) . ? C9 C13 1.600(3) . ? C10 C17 1.558(3) . ? C10 C11 1.608(3) . ? C11 C20 1.500(3) . ? C11 C12 1.533(3) . ? C11 C15 1.543(3) . ? C12 O1 1.204(2) . ? C12 C13 1.528(3) . ? C13 C26 1.508(3) . ? C13 C14 1.545(3) . ? C14 C19 1.517(3) . ? C14 C15 1.593(3) . ? C14 H14 1.0000 . ? C15 C16 1.523(3) . ? C15 H15 1.0000 . ? C16 O2 1.209(2) . ? C16 C17 1.505(3) . ? C17 C18 1.583(3) . ? C17 H17 1.0000 . ? C18 C19 1.509(3) . ? C18 H18 1.0000 . ? C19 O3 1.215(3) . ? C20 C21 1.390(3) . ? C20 C25 1.397(3) . ? C21 C22 1.380(3) . ? C21 H21 0.9500 . ? C22 C23 1.380(3) . ? C22 H22 0.9500 . ? C23 C24 1.384(3) . ? C23 H23 0.9500 . ? C24 C25 1.380(3) . ? C24 H24 0.9500 . ? C25 H25 0.9500 . ? C26 C31 1.385(3) . ? C26 C27 1.396(3) . ? C27 C28 1.388(3) . ? C27 H27 0.9500 . ? C28 C29 1.375(3) . ? C28 H28 0.9500 . ? C29 C30 1.381(3) . ? C29 H29 0.9500 . ? C30 C31 1.387(3) . ? C30 H30 0.9500 . ? C31 H31 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 C2 C1 C1A 122.0(2) . . ? C2 C1 H1 119.0 . . ? C1A C1 H1 119.0 . . ? C1 C1A C4A 119.4(2) . . ? C1 C1A C10 119.6(2) . . ? C4A C1A C10 120.99(19) . . ? C3 C2 C1 118.4(2) . . ? C3 C2 H2 120.8 . . ? C1 C2 H2 120.8 . . ? C2 C3 C4 120.4(2) . . ? C2 C3 H3 119.8 . . ? C4 C3 H3 119.8 . . ? C3 C4 C4A 121.7(2) . . ? C3 C4 H4 119.2 . . ? C4A C4 H4 119.2 . . ? C1A C4A C4 117.6(2) . . ? C1A C4A C5A 120.3(2) . . ? C4 C4A C5A 121.6(2) . . ? C6 C5 C5A 121.5(2) . . ? C6 C5 H5 119.2 . . ? C5A C5 H5 119.2 . . ? C8A C5A C5 117.6(2) . . ? C8A C5A C4A 121.5(2) . . ? C5 C5A C4A 120.4(2) . . ? C7 C6 C5 120.4(2) . . ? C7 C6 H6 119.8 . . ? C5 C6 H6 119.8 . . ? C6 C7 C8 118.8(2) . . ? C6 C7 H7 120.6 . . ? C8 C7 H7 120.6 . . ? C7 C8 C8A 121.7(2) . . ? C7 C8 H8 119.1 . . ? C8A C8 H8 119.1 . . ? C8 C8A C5A 119.8(2) . . ? C8 C8A C9 119.5(2) . . ? C5A C8A C9 120.64(19) . . ? C8A C9 C18 117.57(18) . . ? C8A C9 C10 116.94(18) . . ? C18 C9 C10 90.41(15) . . ? C8A C9 C13 116.87(17) . . ? C18 C9 C13 106.71(17) . . ? C10 C9 C13 104.65(16) . . ? C1A C10 C17 119.30(17) . . ? C1A C10 C9 117.23(18) . . ? C17 C10 C9 90.15(16) . . ? C1A C10 C11 116.26(18) . . ? C17 C10 C11 106.02(16) . . ? C9 C10 C11 104.06(16) . . ? C20 C11 C12 117.42(18) . . ? C20 C11 C15 116.37(18) . . ? C12 C11 C15 101.39(17) . . ? C20 C11 C10 118.72(17) . . ? C12 C11 C10 99.47(15) . . ? C15 C11 C10 100.28(17) . . ? O1 C12 C13 130.5(2) . . ? O1 C12 C11 128.4(2) . . ? C13 C12 C11 101.09(18) . . ? C26 C13 C12 118.49(18) . . ? C26 C13 C14 116.39(18) . . ? C12 C13 C14 101.67(17) . . ? C26 C13 C9 117.26(17) . . ? C12 C13 C9 99.79(16) . . ? C14 C13 C9 100.11(16) . . ? C19 C14 C13 104.66(17) . . ? C19 C14 C15 106.59(16) . . ? C13 C14 C15 104.15(18) . . ? C19 C14 H14 113.5 . . ? C13 C14 H14 113.5 . . ? C15 C14 H14 113.5 . . ? C16 C15 C11 102.66(17) . . ? C16 C15 C14 109.38(17) . . ? C11 C15 C14 104.72(16) . . ? C16 C15 H15 113.1 . . ? C11 C15 H15 113.1 . . ? C14 C15 H15 113.1 . . ? O2 C16 C17 128.2(2) . . ? O2 C16 C15 127.6(2) . . ? C17 C16 C15 104.24(17) . . ? C16 C17 C10 104.88(17) . . ? C16 C17 C18 108.93(17) . . ? C10 C17 C18 89.84(15) . . ? C16 C17 H17 116.6 . . ? C10 C17 H17 116.6 . . ? C18 C17 H17 116.6 . . ? C19 C18 C9 105.48(17) . . ? C19 C18 C17 107.78(17) . . ? C9 C18 C17 89.59(16) . . ? C19 C18 H18 116.8 . . ? C9 C18 H18 116.8 . . ? C17 C18 H18 116.8 . . ? O3 C19 C18 127.5(2) . . ? O3 C19 C14 128.0(2) . . ? C18 C19 C14 104.38(19) . . ? C21 C20 C25 118.0(2) . . ? C21 C20 C11 121.7(2) . . ? C25 C20 C11 120.4(2) . . ? C22 C21 C20 120.8(2) . . ? C22 C21 H21 119.6 . . ? C20 C21 H21 119.6 . . ? C21 C22 C23 120.9(2) . . ? C21 C22 H22 119.6 . . ? C23 C22 H22 119.6 . . ? C22 C23 C24 118.9(2) . . ? C22 C23 H23 120.5 . . ? C24 C23 H23 120.5 . . ? C25 C24 C23 120.5(2) . . ? C25 C24 H24 119.7 . . ? C23 C24 H24 119.7 . . ? C24 C25 C20 120.9(2) . . ? C24 C25 H25 119.5 . . ? C20 C25 H25 119.5 . . ? C31 C26 C27 118.0(2) . . ? C31 C26 C13 121.2(2) . . ? C27 C26 C13 120.7(2) . . ? C28 C27 C26 120.7(2) . . ? C28 C27 H27 119.6 . . ? C26 C27 H27 119.6 . . ? C29 C28 C27 120.1(2) . . ? C29 C28 H28 119.9 . . ? C27 C28 H28 119.9 . . ? C28 C29 C30 120.0(2) . . ? C28 C29 H29 120.0 . . ? C30 C29 H29 120.0 . . ? C29 C30 C31 119.7(2) . . ? C29 C30 H30 120.1 . . ? C31 C30 H30 120.1 . . ? C26 C31 C30 121.3(2) . . ? C26 C31 H31 119.3 . . ? C30 C31 H31 119.3 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C2 C1 C1A C4A 5.6(3) . . . . ? C2 C1 C1A C10 -173.8(2) . . . . ? C1A C1 C2 C3 0.7(3) . . . . ? C1 C2 C3 C4 -3.8(3) . . . . ? C2 C3 C4 C4A 0.6(3) . . . . ? C1 C1A C4A C4 -8.6(3) . . . . ? C10 C1A C4A C4 170.84(19) . . . . ? C1 C1A C4A C5A 164.49(19) . . . . ? C10 C1A C4A C5A -16.1(3) . . . . ? C3 C4 C4A C1A 5.6(3) . . . . ? C3 C4 C4A C5A -167.33(19) . . . . ? C6 C5 C5A C8A -1.1(3) . . . . ? C6 C5 C5A C4A 170.69(19) . . . . ? C1A C4A C5A C8A 5.9(3) . . . . ? C4 C4A C5A C8A 178.6(2) . . . . ? C1A C4A C5A C5 -165.6(2) . . . . ? C4 C4A C5A C5 7.2(3) . . . . ? C5A C5 C6 C7 -1.2(3) . . . . ? C5 C6 C7 C8 1.9(3) . . . . ? C6 C7 C8 C8A -0.2(3) . . . . ? C7 C8 C8A C5A -2.1(3) . . . . ? C7 C8 C8A C9 -179.50(19) . . . . ? C5 C5A C8A C8 2.7(3) . . . . ? C4A C5A C8A C8 -168.98(18) . . . . ? C5 C5A C8A C9 -179.95(18) . . . . ? C4A C5A C8A C9 8.4(3) . . . . ? C8 C8A C9 C18 59.7(3) . . . . ? C5A C8A C9 C18 -117.6(2) . . . . ? C8 C8A C9 C10 165.67(18) . . . . ? C5A C8A C9 C10 -11.7(3) . . . . ? C8 C8A C9 C13 -69.2(3) . . . . ? C5A C8A C9 C13 113.5(2) . . . . ? C1 C1A C10 C17 -61.7(3) . . . . ? C4A C1A C10 C17 118.9(2) . . . . ? C1 C1A C10 C9 -168.68(18) . . . . ? C4A C1A C10 C9 11.9(3) . . . . ? C1 C1A C10 C11 67.4(3) . . . . ? C4A C1A C10 C11 -112.1(2) . . . . ? C8A C9 C10 C1A 1.8(3) . . . . ? C18 C9 C10 C1A 123.37(19) . . . . ? C13 C9 C10 C1A -129.22(19) . . . . ? C8A C9 C10 C17 -121.64(18) . . . . ? C18 C9 C10 C17 -0.12(15) . . . . ? C13 C9 C10 C17 107.29(17) . . . . ? C8A C9 C10 C11 131.79(18) . . . . ? C18 C9 C10 C11 -106.69(17) . . . . ? C13 C9 C10 C11 0.7(2) . . . . ? C1A C10 C11 C20 -30.2(3) . . . . ? C17 C10 C11 C20 105.0(2) . . . . ? C9 C10 C11 C20 -160.70(18) . . . . ? C1A C10 C11 C12 98.4(2) . . . . ? C17 C10 C11 C12 -126.39(17) . . . . ? C9 C10 C11 C12 -32.1(2) . . . . ? C1A C10 C11 C15 -158.07(17) . . . . ? C17 C10 C11 C15 -22.88(19) . . . . ? C9 C10 C11 C15 71.41(18) . . . . ? C20 C11 C12 O1 2.9(3) . . . . ? C15 C11 C12 O1 130.8(2) . . . . ? C10 C11 C12 O1 -126.6(2) . . . . ? C20 C11 C12 C13 -177.37(18) . . . . ? C15 C11 C12 C13 -49.42(19) . . . . ? C10 C11 C12 C13 53.18(19) . . . . ? O1 C12 C13 C26 -1.5(3) . . . . ? C11 C12 C13 C26 178.70(17) . . . . ? O1 C12 C13 C14 -130.5(2) . . . . ? C11 C12 C13 C14 49.77(18) . . . . ? O1 C12 C13 C9 127.0(2) . . . . ? C11 C12 C13 C9 -52.80(18) . . . . ? C8A C9 C13 C26 29.3(3) . . . . ? C18 C9 C13 C26 -104.7(2) . . . . ? C10 C9 C13 C26 160.37(19) . . . . ? C8A C9 C13 C12 -100.0(2) . . . . ? C18 C9 C13 C12 126.02(18) . . . . ? C10 C9 C13 C12 31.1(2) . . . . ? C8A C9 C13 C14 156.12(19) . . . . ? C18 C9 C13 C14 22.2(2) . . . . ? C10 C9 C13 C14 -72.77(19) . . . . ? C26 C13 C14 C19 87.7(2) . . . . ? C12 C13 C14 C19 -142.01(17) . . . . ? C9 C13 C14 C19 -39.7(2) . . . . ? C26 C13 C14 C15 -160.53(17) . . . . ? C12 C13 C14 C15 -30.28(19) . . . . ? C9 C13 C14 C15 72.03(18) . . . . ? C20 C11 C15 C16 -87.4(2) . . . . ? C12 C11 C15 C16 143.92(16) . . . . ? C10 C11 C15 C16 41.98(19) . . . . ? C20 C11 C15 C14 158.30(16) . . . . ? C12 C11 C15 C14 29.7(2) . . . . ? C10 C11 C15 C14 -72.27(18) . . . . ? C19 C14 C15 C16 1.2(2) . . . . ? C13 C14 C15 C16 -109.15(19) . . . . ? C19 C14 C15 C11 110.61(19) . . . . ? C13 C14 C15 C11 0.3(2) . . . . ? C11 C15 C16 O2 132.4(2) . . . . ? C14 C15 C16 O2 -116.8(2) . . . . ? C11 C15 C16 C17 -47.4(2) . . . . ? C14 C15 C16 C17 63.4(2) . . . . ? O2 C16 C17 C10 -148.2(2) . . . . ? C15 C16 C17 C10 31.5(2) . . . . ? O2 C16 C17 C18 116.7(3) . . . . ? C15 C16 C17 C18 -63.6(2) . . . . ? C1A C10 C17 C16 128.79(19) . . . . ? C9 C10 C17 C16 -109.46(17) . . . . ? C11 C10 C17 C16 -4.8(2) . . . . ? C1A C10 C17 C18 -121.64(19) . . . . ? C9 C10 C17 C18 0.12(15) . . . . ? C11 C10 C17 C18 104.80(17) . . . . ? C8A C9 C18 C19 -130.54(19) . . . . ? C10 C9 C18 C19 108.47(17) . . . . ? C13 C9 C18 C19 3.0(2) . . . . ? C8A C9 C18 C17 121.11(19) . . . . ? C10 C9 C18 C17 0.12(15) . . . . ? C13 C9 C18 C17 -105.33(16) . . . . ? C16 C17 C18 C19 -0.6(2) . . . . ? C10 C17 C18 C19 -106.26(18) . . . . ? C16 C17 C18 C9 105.58(18) . . . . ? C10 C17 C18 C9 -0.12(15) . . . . ? C9 C18 C19 O3 154.8(2) . . . . ? C17 C18 C19 O3 -110.6(2) . . . . ? C9 C18 C19 C14 -28.0(2) . . . . ? C17 C18 C19 C14 66.7(2) . . . . ? C13 C14 C19 O3 -139.1(2) . . . . ? C15 C14 C19 O3 111.0(3) . . . . ? C13 C14 C19 C18 43.7(2) . . . . ? C15 C14 C19 C18 -66.3(2) . . . . ? C12 C11 C20 C21 132.7(2) . . . . ? C15 C11 C20 C21 12.4(3) . . . . ? C10 C11 C20 C21 -107.6(2) . . . . ? C12 C11 C20 C25 -47.0(3) . . . . ? C15 C11 C20 C25 -167.35(18) . . . . ? C10 C11 C20 C25 72.7(3) . . . . ? C25 C20 C21 C22 0.2(3) . . . . ? C11 C20 C21 C22 -179.47(19) . . . . ? C20 C21 C22 C23 -0.9(3) . . . . ? C21 C22 C23 C24 0.9(3) . . . . ? C22 C23 C24 C25 -0.2(3) . . . . ? C23 C24 C25 C20 -0.4(3) . . . . ? C21 C20 C25 C24 0.4(3) . . . . ? C11 C20 C25 C24 -179.90(18) . . . . ? C12 C13 C26 C31 -151.4(2) . . . . ? C14 C13 C26 C31 -29.7(3) . . . . ? C9 C13 C26 C31 88.8(3) . . . . ? C12 C13 C26 C27 31.2(3) . . . . ? C14 C13 C26 C27 152.99(19) . . . . ? C9 C13 C26 C27 -88.6(2) . . . . ? C31 C26 C27 C28 -1.2(3) . . . . ? C13 C26 C27 C28 176.21(18) . . . . ? C26 C27 C28 C29 -0.4(3) . . . . ? C27 C28 C29 C30 1.1(3) . . . . ? C28 C29 C30 C31 -0.3(3) . . . . ? C27 C26 C31 C30 2.1(3) . . . . ? C13 C26 C31 C30 -175.35(18) . . . . ? C29 C30 C31 C26 -1.3(3) . . . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.189 _refine_diff_density_min -0.185 _refine_diff_density_rms 0.042