# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_shelxl _database_code_depnum_ccdc_archive 'CCDC 888070' #TrackingRef '12020_web_deposit_cif_file_0_Dr.KannupalSrinivasan_1340169674.dihydronaphthalene.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C33 H28 O4' _chemical_formula_sum 'C33 H28 O4' _chemical_formula_weight 488.55 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 Monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 13.3763(2) _cell_length_b 18.3674(2) _cell_length_c 10.67070(10) _cell_angle_alpha 90.00 _cell_angle_beta 98.9390(10) _cell_angle_gamma 90.00 _cell_volume 2589.82(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 1.54 _cell_measurement_theta_max 20.53 _exptl_crystal_description Needle _exptl_crystal_colour brown _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.253 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1032 _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.9635 _exptl_absorpt_correction_T_max 0.9823 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 32650 _diffrn_reflns_av_R_equivalents 0.0355 _diffrn_reflns_av_sigmaI/netI 0.0163 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 1.54 _diffrn_reflns_theta_max 20.53 _reflns_number_total 2600 _reflns_number_gt 2160 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _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^)+(0.0639P)^2^+1.2650P] 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(11) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2600 _refine_ls_number_parameters 359 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0513 _refine_ls_R_factor_gt 0.0419 _refine_ls_wR_factor_ref 0.1199 _refine_ls_wR_factor_gt 0.1112 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.031 _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 0.2633(2) -0.07142(14) 0.1121(2) 0.0466(7) Uani 1 1 d . . . C2 C 0.3105(2) 0.00159(14) 0.0765(3) 0.0465(7) Uani 1 1 d . . . C3 C 0.2292(2) 0.05680(13) 0.0292(2) 0.0458(7) Uani 1 1 d . . . C4 C 0.1392(2) 0.05520(15) 0.0694(2) 0.0475(7) Uani 1 1 d . . . C5 C 0.11321(18) 0.00002(13) 0.1570(2) 0.0450(7) Uani 1 1 d . . . C6 C 0.17566(18) -0.06031(14) 0.1835(2) 0.0454(7) Uani 1 1 d . . . C7 C 0.1539(2) -0.11118(14) 0.2713(2) 0.0525(7) Uani 1 1 d . . . H7 H 0.1957 -0.1516 0.2890 0.063 Uiso 1 1 calc R . . C8 C 0.0707(2) -0.10276(15) 0.3331(3) 0.0536(7) Uani 1 1 d . . . C9 C 0.00718(19) -0.04267(15) 0.3051(3) 0.0509(7) Uani 1 1 d . . . C10 C 0.02760(19) 0.00729(14) 0.2178(3) 0.0495(7) Uani 1 1 d . . . H10 H -0.0157 0.0467 0.1982 0.059 Uiso 1 1 calc R . . C11 C 0.2322(2) -0.11595(13) -0.0085(3) 0.0512(7) Uani 1 1 d . . . C12 C 0.3123(2) -0.15315(14) -0.0690(3) 0.0547(8) Uani 1 1 d . . . C13 C 0.2851(3) -0.18259(15) -0.1898(3) 0.0704(9) Uani 1 1 d . . . H13 H 0.2188 -0.1778 -0.2311 0.084 Uiso 1 1 calc R . . C14 C 0.3554(4) -0.21881(18) -0.2490(4) 0.0896(12) Uani 1 1 d . . . H14 H 0.3366 -0.2383 -0.3297 0.107 Uiso 1 1 calc R . . C15 C 0.4530(4) -0.22590(19) -0.1884(5) 0.0970(13) Uani 1 1 d . . . H15 H 0.5004 -0.2503 -0.2281 0.116 Uiso 1 1 calc R . . C16 C 0.4813(3) -0.19728(18) -0.0692(4) 0.0860(11) Uani 1 1 d . . . H16 H 0.5476 -0.2025 -0.0284 0.103 Uiso 1 1 calc R . . C17 C 0.4113(2) -0.16076(15) -0.0098(3) 0.0671(9) Uani 1 1 d . . . H17 H 0.4309 -0.1412 0.0706 0.081 Uiso 1 1 calc R . . C18 C 0.38584(19) 0.03050(14) 0.1867(2) 0.0473(7) Uani 1 1 d . . . C19 C 0.4863(2) 0.00930(15) 0.2004(3) 0.0573(8) Uani 1 1 d . . . H19 H 0.5079 -0.0198 0.1385 0.069 Uiso 1 1 calc R . . C20 C 0.5545(2) 0.03054(17) 0.3037(3) 0.0668(9) Uani 1 1 d . . . H20 H 0.6213 0.0149 0.3106 0.080 Uiso 1 1 calc R . . C21 C 0.5268(2) 0.07423(16) 0.3973(3) 0.0627(8) Uani 1 1 d . . . C22 C 0.4267(2) 0.09641(16) 0.3832(3) 0.0645(8) Uani 1 1 d . . . H22 H 0.4057 0.1263 0.4445 0.077 Uiso 1 1 calc R . . C23 C 0.3573(2) 0.07504(15) 0.2799(3) 0.0573(8) Uani 1 1 d . . . H23 H 0.2906 0.0908 0.2728 0.069 Uiso 1 1 calc R . . C24 C 0.2529(2) 0.11132(15) -0.0624(3) 0.0598(8) Uani 1 1 d . . . C25 C 0.2048(2) 0.18463(15) -0.0701(3) 0.0545(8) Uani 1 1 d . . . C26 C 0.2284(3) 0.2326(2) 0.0280(4) 0.0951(12) Uani 1 1 d . . . H26 H 0.2669 0.2167 0.1031 0.114 Uiso 1 1 calc R . . C27 C 0.1965(4) 0.3040(2) 0.0180(5) 0.1121(14) Uani 1 1 d . . . H27 H 0.2145 0.3360 0.0853 0.135 Uiso 1 1 calc R . . C28 C 0.1397(4) 0.3271(2) -0.0885(6) 0.1055(15) Uani 1 1 d . . . H28 H 0.1191 0.3755 -0.0953 0.127 Uiso 1 1 calc R . . C29 C 0.1123(4) 0.2825(3) -0.1839(5) 0.1188(15) Uani 1 1 d . . . H29 H 0.0707 0.2990 -0.2564 0.143 Uiso 1 1 calc R . . C30 C 0.1464(3) 0.2092(2) -0.1764(4) 0.0982(12) Uani 1 1 d . . . H30 H 0.1284 0.1780 -0.2449 0.118 Uiso 1 1 calc R . . C31 C 0.1023(3) -0.21325(19) 0.4516(4) 0.0996(13) Uani 1 1 d . . . H31A H 0.0991 -0.2426 0.3767 0.149 Uiso 1 1 calc R . . H31B H 0.0756 -0.2402 0.5160 0.149 Uiso 1 1 calc R . . H31C H 0.1714 -0.2004 0.4817 0.149 Uiso 1 1 calc R . . C32 C -0.1385(2) 0.02044(17) 0.3504(3) 0.0788(10) Uani 1 1 d . . . H32A H -0.0996 0.0644 0.3659 0.118 Uiso 1 1 calc R . . H32B H -0.1874 0.0181 0.4072 0.118 Uiso 1 1 calc R . . H32C H -0.1727 0.0203 0.2643 0.118 Uiso 1 1 calc R . . C33 C 0.6026(4) 0.0967(3) 0.5105(4) 0.0883(12) Uani 1 1 d . . . O1 O 0.04423(15) -0.14899(11) 0.42262(19) 0.0719(6) Uani 1 1 d . . . O2 O -0.07324(14) -0.04044(10) 0.3705(2) 0.0706(6) Uani 1 1 d . . . O3 O 0.14410(17) -0.11996(10) -0.05777(19) 0.0690(6) Uani 1 1 d . . . O4 O 0.3135(2) 0.09712(14) -0.1330(3) 0.1187(11) Uani 1 1 d . . . H1 H 0.3168(18) -0.0977(12) 0.166(2) 0.042(7) Uiso 1 1 d . . . H2 H 0.3462(16) -0.0083(11) 0.009(2) 0.034(6) Uiso 1 1 d . . . H3 H 0.0905(18) 0.0912(13) 0.042(2) 0.040(7) Uiso 1 1 d . . . H33A H 0.633(4) 0.060(3) 0.545(5) 0.16(2) Uiso 1 1 d . . . H33B H 0.621(3) 0.141(3) 0.509(4) 0.129(18) Uiso 1 1 d . . . H33C H 0.567(4) 0.104(3) 0.591(5) 0.17(2) 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 C1 0.0466(16) 0.0428(16) 0.0511(17) 0.0032(14) 0.0097(14) 0.0069(13) C2 0.0489(16) 0.0455(16) 0.0488(17) -0.0013(13) 0.0188(15) 0.0032(14) C3 0.0513(18) 0.0432(16) 0.0436(15) -0.0010(12) 0.0096(13) 0.0029(13) C4 0.0490(18) 0.0412(17) 0.0515(17) -0.0007(14) 0.0049(14) 0.0089(15) C5 0.0423(16) 0.0406(15) 0.0513(16) 0.0024(13) 0.0054(13) 0.0020(14) C6 0.0440(16) 0.0441(16) 0.0486(16) 0.0019(13) 0.0093(13) 0.0020(14) C7 0.0520(18) 0.0470(17) 0.0603(18) 0.0060(14) 0.0145(15) 0.0098(13) C8 0.0553(18) 0.0491(18) 0.0596(18) 0.0071(15) 0.0190(15) 0.0026(15) C9 0.0439(17) 0.0502(18) 0.0629(18) 0.0008(15) 0.0216(14) 0.0020(14) C10 0.0412(16) 0.0434(16) 0.0639(18) -0.0004(14) 0.0085(14) 0.0062(13) C11 0.059(2) 0.0375(16) 0.0586(18) 0.0064(13) 0.0128(16) 0.0028(14) C12 0.069(2) 0.0393(16) 0.061(2) 0.0028(14) 0.0282(16) 0.0009(14) C13 0.100(2) 0.0498(18) 0.067(2) -0.0003(16) 0.0322(19) -0.0023(18) C14 0.138(4) 0.064(2) 0.079(2) -0.0090(19) 0.056(3) -0.001(2) C15 0.119(4) 0.064(2) 0.127(4) -0.008(2) 0.080(3) 0.007(2) C16 0.082(2) 0.067(2) 0.119(3) -0.007(2) 0.048(2) 0.0063(19) C17 0.070(2) 0.0516(18) 0.087(2) -0.0015(16) 0.036(2) 0.0058(16) C18 0.0450(18) 0.0467(16) 0.0523(17) 0.0029(14) 0.0146(14) 0.0013(13) C19 0.0485(19) 0.0591(18) 0.067(2) -0.0031(15) 0.0192(16) 0.0028(15) C20 0.0463(18) 0.071(2) 0.083(2) 0.0027(19) 0.0096(18) 0.0020(16) C21 0.060(2) 0.0601(19) 0.065(2) 0.0068(16) 0.0012(17) -0.0076(16) C22 0.066(2) 0.066(2) 0.063(2) -0.0081(16) 0.0114(17) 0.0022(17) C23 0.0473(17) 0.0628(18) 0.0627(19) -0.0059(16) 0.0109(16) 0.0049(14) C24 0.0667(19) 0.057(2) 0.0602(19) 0.0078(16) 0.0257(16) 0.0089(16) C25 0.0596(18) 0.0520(19) 0.0550(19) 0.0127(16) 0.0187(15) 0.0007(15) C26 0.103(3) 0.083(3) 0.098(3) -0.015(2) 0.014(2) 0.033(2) C27 0.134(4) 0.074(3) 0.140(4) -0.013(3) 0.055(3) 0.017(3) C28 0.131(4) 0.069(3) 0.133(4) 0.038(3) 0.074(3) 0.023(3) C29 0.140(4) 0.106(4) 0.106(4) 0.044(3) 0.004(3) 0.032(3) C30 0.121(3) 0.078(3) 0.089(3) 0.007(2) -0.004(2) 0.008(2) C31 0.105(3) 0.083(3) 0.124(3) 0.052(2) 0.058(2) 0.034(2) C32 0.061(2) 0.075(2) 0.107(3) 0.0007(19) 0.0354(18) 0.0184(18) C33 0.088(3) 0.082(3) 0.086(3) 0.002(2) -0.015(2) -0.013(3) O1 0.0765(14) 0.0616(13) 0.0864(15) 0.0246(11) 0.0405(12) 0.0140(11) O2 0.0599(12) 0.0640(13) 0.0964(15) 0.0122(11) 0.0383(12) 0.0116(11) O3 0.0660(15) 0.0632(13) 0.0752(14) -0.0120(10) 0.0033(12) 0.0056(11) O4 0.157(2) 0.0973(19) 0.126(2) 0.0483(16) 0.098(2) 0.0546(18) _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 C6 1.507(4) . ? C1 C11 1.527(4) . ? C1 C2 1.554(4) . ? C1 H1 0.98(2) . ? C2 C3 1.515(4) . ? C2 C18 1.521(4) . ? C2 H2 0.94(2) . ? C3 C4 1.341(4) . ? C3 C24 1.468(4) . ? C4 C5 1.457(4) . ? C4 H3 0.94(2) . ? C5 C6 1.390(3) . ? C5 C10 1.407(4) . ? C6 C7 1.386(4) . ? C7 C8 1.388(4) . ? C7 H7 0.9300 . ? C8 O1 1.365(3) . ? C8 C9 1.397(4) . ? C9 C10 1.365(4) . ? C9 O2 1.370(3) . ? C10 H10 0.9300 . ? C11 O3 1.216(3) . ? C11 C12 1.499(4) . ? C12 C17 1.383(4) . ? C12 C13 1.393(4) . ? C13 C14 1.383(5) . ? C13 H13 0.9300 . ? C14 C15 1.370(5) . ? C14 H14 0.9300 . ? C15 C16 1.374(5) . ? C15 H15 0.9300 . ? C16 C17 1.383(4) . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? C18 C19 1.385(4) . ? C18 C23 1.386(4) . ? C19 C20 1.374(4) . ? C19 H19 0.9300 . ? C20 C21 1.376(4) . ? C20 H20 0.9300 . ? C21 C22 1.386(4) . ? C21 C33 1.509(5) . ? C22 C23 1.384(4) . ? C22 H22 0.9300 . ? C23 H23 0.9300 . ? C24 O4 1.218(3) . ? C24 C25 1.489(4) . ? C25 C30 1.351(4) . ? C25 C26 1.367(4) . ? C26 C27 1.379(5) . ? C26 H26 0.9300 . ? C27 C28 1.334(6) . ? C27 H27 0.9300 . ? C28 C29 1.314(6) . ? C28 H28 0.9300 . ? C29 C30 1.420(6) . ? C29 H29 0.9300 . ? C30 H30 0.9300 . ? C31 O1 1.420(4) . ? C31 H31A 0.9600 . ? C31 H31B 0.9600 . ? C31 H31C 0.9600 . ? C32 O2 1.414(3) . ? C32 H32A 0.9600 . ? C32 H32B 0.9600 . ? C32 H32C 0.9600 . ? C33 H33A 0.83(5) . ? C33 H33B 0.85(4) . ? C33 H33C 1.06(6) . ? 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 C6 C1 C11 111.5(2) . . ? C6 C1 C2 112.6(2) . . ? C11 C1 C2 108.9(2) . . ? C6 C1 H1 108.8(13) . . ? C11 C1 H1 108.3(13) . . ? C2 C1 H1 106.5(13) . . ? C3 C2 C18 112.3(2) . . ? C3 C2 C1 111.2(2) . . ? C18 C2 C1 110.9(2) . . ? C3 C2 H2 107.4(13) . . ? C18 C2 H2 107.7(13) . . ? C1 C2 H2 107.1(13) . . ? C4 C3 C24 121.7(2) . . ? C4 C3 C2 120.9(2) . . ? C24 C3 C2 117.4(2) . . ? C3 C4 C5 122.4(3) . . ? C3 C4 H3 120.0(14) . . ? C5 C4 H3 117.6(14) . . ? C6 C5 C10 119.2(2) . . ? C6 C5 C4 119.3(2) . . ? C10 C5 C4 121.4(2) . . ? C7 C6 C5 119.5(2) . . ? C7 C6 C1 120.8(2) . . ? C5 C6 C1 119.7(2) . . ? C6 C7 C8 121.0(2) . . ? C6 C7 H7 119.5 . . ? C8 C7 H7 119.5 . . ? O1 C8 C7 125.3(2) . . ? O1 C8 C9 115.2(2) . . ? C7 C8 C9 119.5(2) . . ? C10 C9 O2 125.7(2) . . ? C10 C9 C8 119.8(2) . . ? O2 C9 C8 114.5(2) . . ? C9 C10 C5 120.9(2) . . ? C9 C10 H10 119.5 . . ? C5 C10 H10 119.5 . . ? O3 C11 C12 119.7(3) . . ? O3 C11 C1 121.0(2) . . ? C12 C11 C1 119.2(3) . . ? C17 C12 C13 118.5(3) . . ? C17 C12 C11 123.2(3) . . ? C13 C12 C11 118.3(3) . . ? C14 C13 C12 120.7(3) . . ? C14 C13 H13 119.6 . . ? C12 C13 H13 119.6 . . ? C15 C14 C13 119.7(4) . . ? C15 C14 H14 120.1 . . ? C13 C14 H14 120.1 . . ? C14 C15 C16 120.4(3) . . ? C14 C15 H15 119.8 . . ? C16 C15 H15 119.8 . . ? C15 C16 C17 120.1(4) . . ? C15 C16 H16 120.0 . . ? C17 C16 H16 120.0 . . ? C12 C17 C16 120.6(3) . . ? C12 C17 H17 119.7 . . ? C16 C17 H17 119.7 . . ? C19 C18 C23 117.5(2) . . ? C19 C18 C2 119.9(2) . . ? C23 C18 C2 122.5(2) . . ? C20 C19 C18 121.1(3) . . ? C20 C19 H19 119.4 . . ? C18 C19 H19 119.4 . . ? C19 C20 C21 121.9(3) . . ? C19 C20 H20 119.1 . . ? C21 C20 H20 119.1 . . ? C20 C21 C22 117.2(3) . . ? C20 C21 C33 121.2(3) . . ? C22 C21 C33 121.6(4) . . ? C23 C22 C21 121.4(3) . . ? C23 C22 H22 119.3 . . ? C21 C22 H22 119.3 . . ? C22 C23 C18 120.9(3) . . ? C22 C23 H23 119.6 . . ? C18 C23 H23 119.6 . . ? O4 C24 C3 120.0(3) . . ? O4 C24 C25 118.9(2) . . ? C3 C24 C25 121.1(2) . . ? C30 C25 C26 117.5(3) . . ? C30 C25 C24 122.5(3) . . ? C26 C25 C24 119.6(3) . . ? C25 C26 C27 121.5(4) . . ? C25 C26 H26 119.3 . . ? C27 C26 H26 119.3 . . ? C28 C27 C26 119.8(4) . . ? C28 C27 H27 120.1 . . ? C26 C27 H27 120.1 . . ? C29 C28 C27 121.0(4) . . ? C29 C28 H28 119.5 . . ? C27 C28 H28 119.5 . . ? C28 C29 C30 120.0(4) . . ? C28 C29 H29 120.0 . . ? C30 C29 H29 120.0 . . ? C25 C30 C29 120.2(4) . . ? C25 C30 H30 119.9 . . ? C29 C30 H30 119.9 . . ? O1 C31 H31A 109.5 . . ? O1 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? O1 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? O2 C32 H32A 109.5 . . ? O2 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? O2 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? C21 C33 H33A 111(4) . . ? C21 C33 H33B 114(3) . . ? H33A C33 H33B 130(5) . . ? C21 C33 H33C 111(3) . . ? H33A C33 H33C 90(4) . . ? H33B C33 H33C 93(4) . . ? C8 O1 C31 118.5(2) . . ? C9 O2 C32 117.5(2) . . ? 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 C6 C1 C2 C3 -42.5(3) . . . . ? C11 C1 C2 C3 81.8(3) . . . . ? C6 C1 C2 C18 83.2(3) . . . . ? C11 C1 C2 C18 -152.5(2) . . . . ? C18 C2 C3 C4 -96.2(3) . . . . ? C1 C2 C3 C4 28.7(3) . . . . ? C18 C2 C3 C24 84.2(3) . . . . ? C1 C2 C3 C24 -150.9(2) . . . . ? C24 C3 C4 C5 177.9(2) . . . . ? C2 C3 C4 C5 -1.7(4) . . . . ? C3 C4 C5 C6 -11.4(4) . . . . ? C3 C4 C5 C10 167.0(2) . . . . ? C10 C5 C6 C7 -1.5(4) . . . . ? C4 C5 C6 C7 177.0(2) . . . . ? C10 C5 C6 C1 175.7(2) . . . . ? C4 C5 C6 C1 -5.9(3) . . . . ? C11 C1 C6 C7 87.3(3) . . . . ? C2 C1 C6 C7 -149.9(2) . . . . ? C11 C1 C6 C5 -89.8(3) . . . . ? C2 C1 C6 C5 32.9(3) . . . . ? C5 C6 C7 C8 0.0(4) . . . . ? C1 C6 C7 C8 -177.2(2) . . . . ? C6 C7 C8 O1 -178.6(2) . . . . ? C6 C7 C8 C9 0.9(4) . . . . ? O1 C8 C9 C10 179.3(2) . . . . ? C7 C8 C9 C10 -0.3(4) . . . . ? O1 C8 C9 O2 -1.3(3) . . . . ? C7 C8 C9 O2 179.1(2) . . . . ? O2 C9 C10 C5 179.4(2) . . . . ? C8 C9 C10 C5 -1.3(4) . . . . ? C6 C5 C10 C9 2.2(4) . . . . ? C4 C5 C10 C9 -176.2(2) . . . . ? C6 C1 C11 O3 21.8(3) . . . . ? C2 C1 C11 O3 -103.1(3) . . . . ? C6 C1 C11 C12 -160.2(2) . . . . ? C2 C1 C11 C12 74.9(3) . . . . ? O3 C11 C12 C17 -169.7(3) . . . . ? C1 C11 C12 C17 12.3(4) . . . . ? O3 C11 C12 C13 9.1(4) . . . . ? C1 C11 C12 C13 -168.9(2) . . . . ? C17 C12 C13 C14 0.2(4) . . . . ? C11 C12 C13 C14 -178.7(3) . . . . ? C12 C13 C14 C15 0.0(5) . . . . ? C13 C14 C15 C16 0.0(5) . . . . ? C14 C15 C16 C17 -0.3(5) . . . . ? C13 C12 C17 C16 -0.4(4) . . . . ? C11 C12 C17 C16 178.3(3) . . . . ? C15 C16 C17 C12 0.5(5) . . . . ? C3 C2 C18 C19 -146.5(2) . . . . ? C1 C2 C18 C19 88.5(3) . . . . ? C3 C2 C18 C23 37.0(3) . . . . ? C1 C2 C18 C23 -88.1(3) . . . . ? C23 C18 C19 C20 1.2(4) . . . . ? C2 C18 C19 C20 -175.5(2) . . . . ? C18 C19 C20 C21 -0.7(4) . . . . ? C19 C20 C21 C22 -0.2(4) . . . . ? C19 C20 C21 C33 179.6(3) . . . . ? C20 C21 C22 C23 0.5(4) . . . . ? C33 C21 C22 C23 -179.3(3) . . . . ? C21 C22 C23 C18 0.0(4) . . . . ? C19 C18 C23 C22 -0.9(4) . . . . ? C2 C18 C23 C22 175.7(2) . . . . ? C4 C3 C24 O4 -151.7(3) . . . . ? C2 C3 C24 O4 27.9(4) . . . . ? C4 C3 C24 C25 29.0(4) . . . . ? C2 C3 C24 C25 -151.4(3) . . . . ? O4 C24 C25 C30 61.4(4) . . . . ? C3 C24 C25 C30 -119.3(3) . . . . ? O4 C24 C25 C26 -111.3(4) . . . . ? C3 C24 C25 C26 68.1(4) . . . . ? C30 C25 C26 C27 -1.8(5) . . . . ? C24 C25 C26 C27 171.2(3) . . . . ? C25 C26 C27 C28 1.2(6) . . . . ? C26 C27 C28 C29 0.9(7) . . . . ? C27 C28 C29 C30 -2.3(7) . . . . ? C26 C25 C30 C29 0.4(5) . . . . ? C24 C25 C30 C29 -172.4(3) . . . . ? C28 C29 C30 C25 1.7(7) . . . . ? C7 C8 O1 C31 -3.5(4) . . . . ? C9 C8 O1 C31 176.9(3) . . . . ? C10 C9 O2 C32 -3.1(4) . . . . ? C8 C9 O2 C32 177.6(3) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 20.53 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.304 _refine_diff_density_min -0.170 _refine_diff_density_rms 0.030