# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers # This journal is © The Partner Organisations 2014 ####################################################################### # # 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_a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C40 H40' _chemical_formula_weight 520.72 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' _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 9.1290(18) _cell_length_b 12.580(3) _cell_length_c 15.035(3) _cell_angle_alpha 81.14(3) _cell_angle_beta 73.69(3) _cell_angle_gamma 70.31(3) _cell_volume 1556.9(5) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 9949 _cell_measurement_theta_min 2.16 _cell_measurement_theta_max 25.02 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.111 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 560 _exptl_absorpt_coefficient_mu 0.062 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.972 _exptl_absorpt_correction_T_max 0.988 _exptl_absorpt_process_details ; HIGASHI, T. (1995). Abscor-Empirical Absorption Correction based on Fourier Series Approximation. Rigaku Corporation,Tokyo,Japan. ; _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 'Rigaku RAXIS RAPID IP' _diffrn_measurement_method \W _diffrn_detector_area_resol_mean 10.00 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 9949 _diffrn_reflns_av_R_equivalents 0.0622 _diffrn_reflns_av_sigmaI/netI 0.0801 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.16 _diffrn_reflns_theta_max 25.02 _reflns_number_total 5270 _reflns_number_gt 2299 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Rapid-AUTO (Rigaku,2000)' _computing_cell_refinement Rapid-AUTO _computing_data_reduction 'CrystalStructure (Rigaku/MSC,2000)' _computing_structure_solution SHELXS-97,(Sheldrick,1997) _computing_structure_refinement SHELXL-97,(Sheldrick,1997) _computing_molecular_graphics 'Siemens SHELXTL V4.2,(Sheldrick,1990)' _computing_publication_material SHELXL-97,(Sheldrick,1997) _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0460P)^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 constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.031(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 5270 _refine_ls_number_parameters 362 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1273 _refine_ls_R_factor_gt 0.0554 _refine_ls_wR_factor_ref 0.1309 _refine_ls_wR_factor_gt 0.1180 _refine_ls_goodness_of_fit_ref 1.010 _refine_ls_restrained_S_all 1.010 _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 -0.2410(3) 0.6898(2) 0.23817(15) 0.0588(7) Uani 1 1 d . . . C2 C -0.2869(3) 0.8174(2) 0.22644(17) 0.0657(7) Uani 1 1 d . . . C3 C -0.2447(3) 0.8577(2) 0.29812(15) 0.0586(7) Uani 1 1 d . . . C4 C -0.1695(3) 0.7699(2) 0.35202(16) 0.0689(8) Uani 1 1 d . . . C5 C -0.1404(3) 0.65549(19) 0.31454(15) 0.0608(7) Uani 1 1 d . . . C6 C 0.0300(3) 0.6471(2) 0.25801(17) 0.0646(7) Uani 1 1 d . . . C7 C 0.0304(3) 0.69328(19) 0.17030(15) 0.0582(7) Uani 1 1 d . . . C8 C -0.1320(3) 0.7291(2) 0.15287(16) 0.0720(8) Uani 1 1 d . . . C9 C -0.3563(3) 0.6303(2) 0.23051(17) 0.0773(8) Uani 1 1 d . . . H9A H -0.3996 0.6652 0.1773 0.093 Uiso 1 1 calc R . . H9B H -0.4452 0.6440 0.2853 0.093 Uiso 1 1 calc R . . C10 C -0.2881(4) 0.5030(2) 0.22053(19) 0.1040(11) Uani 1 1 d . . . H10A H -0.3711 0.4747 0.2162 0.156 Uiso 1 1 calc R . . H10B H -0.2482 0.4664 0.2737 0.156 Uiso 1 1 calc R . . H10C H -0.2022 0.4877 0.1654 0.156 Uiso 1 1 calc R . . C11 C -0.4301(3) 0.8896(2) 0.18950(17) 0.0772(8) Uani 1 1 d . . . H11A H -0.4396 0.8507 0.1415 0.093 Uiso 1 1 calc R . . H11B H -0.4120 0.9603 0.1614 0.093 Uiso 1 1 calc R . . C12 C -0.5859(3) 0.9152(3) 0.26404(19) 0.1017(10) Uani 1 1 d . . . H12A H -0.6722 0.9615 0.2371 0.153 Uiso 1 1 calc R . . H12B H -0.5779 0.9546 0.3115 0.153 Uiso 1 1 calc R . . H12C H -0.6064 0.8457 0.2908 0.153 Uiso 1 1 calc R . . C13 C -0.2758(3) 0.9790(2) 0.30866(17) 0.0621(7) Uani 1 1 d . . . C14 C -0.3449(3) 1.0233(2) 0.39507(19) 0.0779(8) Uani 1 1 d . . . H14 H -0.3673 0.9752 0.4469 0.094 Uiso 1 1 calc R . . C15 C -0.3810(4) 1.1357(3) 0.4062(2) 0.0981(10) Uani 1 1 d . . . H15 H -0.4294 1.1636 0.4647 0.118 Uiso 1 1 calc R . . C16 C -0.3458(4) 1.2070(3) 0.3312(3) 0.1034(11) Uani 1 1 d . . . H16 H -0.3700 1.2835 0.3390 0.124 Uiso 1 1 calc R . . C17 C -0.2754(4) 1.1676(3) 0.2448(3) 0.0985(10) Uani 1 1 d . . . H17 H -0.2516 1.2169 0.1942 0.118 Uiso 1 1 calc R . . C18 C -0.2390(3) 1.0518(2) 0.23254(19) 0.0824(9) Uani 1 1 d . . . H18 H -0.1907 1.0243 0.1739 0.099 Uiso 1 1 calc R . . C19 C -0.1046(3) 0.7827(2) 0.42857(16) 0.0654(7) Uani 1 1 d . . . C20 C 0.0158(4) 0.8327(2) 0.41065(19) 0.0832(9) Uani 1 1 d . . . H20 H 0.0612 0.8529 0.3496 0.100 Uiso 1 1 calc R . . C21 C 0.0698(4) 0.8531(3) 0.4811(2) 0.1082(11) Uani 1 1 d . . . H21 H 0.1537 0.8839 0.4666 0.130 Uiso 1 1 calc R . . C22 C 0.0019(5) 0.8288(3) 0.5726(2) 0.1189(13) Uani 1 1 d . . . H22 H 0.0356 0.8455 0.6203 0.143 Uiso 1 1 calc R . . C23 C -0.1172(5) 0.7791(3) 0.5914(2) 0.1150(12) Uani 1 1 d . . . H23 H -0.1632 0.7602 0.6527 0.138 Uiso 1 1 calc R . . C24 C -0.1698(4) 0.7567(2) 0.52079(18) 0.0858(9) Uani 1 1 d . . . H24 H -0.2511 0.7232 0.5356 0.103 Uiso 1 1 calc R . . C25 C -0.1573(3) 0.5578(2) 0.38767(16) 0.0795(8) Uani 1 1 d . . . H25A H -0.1195 0.4884 0.3560 0.095 Uiso 1 1 calc R . . H25B H -0.0871 0.5500 0.4279 0.095 Uiso 1 1 calc R . . C26 C -0.3265(4) 0.5699(2) 0.44838(17) 0.0971(10) Uani 1 1 d . . . H26A H -0.3241 0.5056 0.4923 0.146 Uiso 1 1 calc R . . H26B H -0.3965 0.5740 0.4099 0.146 Uiso 1 1 calc R . . H26C H -0.3651 0.6376 0.4811 0.146 Uiso 1 1 calc R . . C27 C 0.1773(3) 0.5951(2) 0.29521(17) 0.0777(8) Uani 1 1 d . . . H27A H 0.1468 0.6016 0.3619 0.093 Uiso 1 1 calc R . . H27B H 0.2520 0.6377 0.2681 0.093 Uiso 1 1 calc R . . C28 C 0.2619(4) 0.4715(3) 0.2754(2) 0.1067(11) Uani 1 1 d . . . H28A H 0.3544 0.4437 0.3007 0.160 Uiso 1 1 calc R . . H28B H 0.2948 0.4645 0.2095 0.160 Uiso 1 1 calc R . . H28C H 0.1898 0.4283 0.3034 0.160 Uiso 1 1 calc R . . C29 C 0.1696(3) 0.7186(2) 0.10212(16) 0.0611(7) Uani 1 1 d . . . C30 C 0.1992(4) 0.8188(3) 0.10074(18) 0.0885(9) Uani 1 1 d . . . H30 H 0.1306 0.8717 0.1431 0.106 Uiso 1 1 calc R . . C31 C 0.3289(4) 0.8433(3) 0.0377(2) 0.0972(10) Uani 1 1 d . . . H31 H 0.3468 0.9115 0.0390 0.117 Uiso 1 1 calc R . . C32 C 0.4282(4) 0.7703(4) -0.0244(2) 0.1041(11) Uani 1 1 d . . . H32 H 0.5141 0.7876 -0.0672 0.125 Uiso 1 1 calc R . . C33 C 0.4022(4) 0.6693(3) -0.0247(2) 0.1212(13) Uani 1 1 d . . . H33 H 0.4717 0.6171 -0.0673 0.145 Uiso 1 1 calc R . . C34 C 0.2729(4) 0.6447(2) 0.03837(19) 0.0940(10) Uani 1 1 d . . . H34 H 0.2562 0.5761 0.0371 0.113 Uiso 1 1 calc R . . C35 C -0.1397(3) 0.7375(2) 0.05349(16) 0.0680(7) Uani 1 1 d . . . C36 C -0.1349(3) 0.8362(2) -0.00044(18) 0.0830(9) Uani 1 1 d . . . H36 H -0.1359 0.8983 0.0265 0.100 Uiso 1 1 calc R . . C37 C -0.1286(4) 0.8436(3) -0.0947(2) 0.0981(10) Uani 1 1 d . . . H37 H -0.1256 0.9106 -0.1302 0.118 Uiso 1 1 calc R . . C38 C -0.1269(4) 0.7537(3) -0.1352(2) 0.1014(11) Uani 1 1 d . . . H38 H -0.1234 0.7594 -0.1981 0.122 Uiso 1 1 calc R . . C39 C -0.1302(4) 0.6547(3) -0.0831(2) 0.0999(10) Uani 1 1 d . . . H39 H -0.1273 0.5925 -0.1108 0.120 Uiso 1 1 calc R . . C40 C -0.1380(3) 0.6475(3) 0.01054(19) 0.0825(9) Uani 1 1 d . . . H40 H -0.1421 0.5804 0.0456 0.099 Uiso 1 1 calc R . . 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 0.0534(17) 0.0622(16) 0.0596(15) -0.0024(12) -0.0048(13) -0.0244(14) C2 0.060(2) 0.0657(18) 0.0694(17) 0.0043(14) -0.0233(15) -0.0152(16) C3 0.0573(18) 0.0616(17) 0.0524(14) 0.0045(13) -0.0073(12) -0.0215(14) C4 0.086(2) 0.0674(18) 0.0589(15) 0.0082(14) -0.0232(15) -0.0321(17) C5 0.067(2) 0.0584(16) 0.0566(14) 0.0073(12) -0.0118(13) -0.0259(14) C6 0.0530(19) 0.0630(16) 0.0699(16) 0.0121(13) -0.0162(14) -0.0144(15) C7 0.0545(19) 0.0605(16) 0.0558(15) 0.0025(12) -0.0081(13) -0.0204(14) C8 0.068(2) 0.101(2) 0.0546(15) 0.0069(14) -0.0131(14) -0.0432(18) C9 0.080(2) 0.088(2) 0.0723(17) -0.0044(15) -0.0078(15) -0.0456(18) C10 0.128(3) 0.096(2) 0.102(2) -0.0113(18) -0.010(2) -0.065(2) C11 0.068(2) 0.0832(19) 0.0764(18) -0.0030(15) -0.0173(17) -0.0202(18) C12 0.064(2) 0.120(3) 0.105(2) -0.0092(19) -0.0148(19) -0.012(2) C13 0.0605(19) 0.0577(17) 0.0635(16) 0.0038(14) -0.0093(14) -0.0206(14) C14 0.081(2) 0.066(2) 0.0809(19) -0.0059(15) -0.0056(16) -0.0268(17) C15 0.099(3) 0.070(2) 0.115(3) -0.012(2) -0.011(2) -0.021(2) C16 0.105(3) 0.064(2) 0.140(3) -0.010(2) -0.031(2) -0.023(2) C17 0.103(3) 0.076(2) 0.119(3) 0.029(2) -0.034(2) -0.041(2) C18 0.091(2) 0.070(2) 0.0821(19) 0.0136(15) -0.0194(16) -0.0292(18) C19 0.073(2) 0.0617(17) 0.0571(16) 0.0056(13) -0.0147(14) -0.0202(16) C20 0.090(3) 0.098(2) 0.0687(18) -0.0023(16) -0.0136(17) -0.044(2) C21 0.112(3) 0.142(3) 0.096(2) -0.011(2) -0.025(2) -0.071(3) C22 0.150(4) 0.155(3) 0.086(3) 0.000(2) -0.044(2) -0.082(3) C23 0.161(4) 0.147(3) 0.0595(19) 0.0128(19) -0.035(2) -0.079(3) C24 0.102(3) 0.096(2) 0.0674(18) 0.0094(16) -0.0203(17) -0.048(2) C25 0.094(2) 0.0745(18) 0.0695(17) 0.0126(14) -0.0112(16) -0.0403(18) C26 0.105(3) 0.115(2) 0.0744(18) 0.0109(17) 0.0002(18) -0.064(2) C27 0.069(2) 0.082(2) 0.0709(17) 0.0170(15) -0.0204(15) -0.0161(18) C28 0.094(3) 0.099(3) 0.103(2) -0.0004(19) -0.0283(19) 0.001(2) C29 0.0521(18) 0.0709(18) 0.0581(15) 0.0052(14) -0.0135(14) -0.0203(16) C30 0.085(2) 0.099(2) 0.087(2) -0.0140(17) 0.0026(18) -0.051(2) C31 0.090(3) 0.117(3) 0.095(2) 0.006(2) -0.010(2) -0.061(2) C32 0.078(3) 0.127(3) 0.094(2) 0.033(2) -0.005(2) -0.045(3) C33 0.096(3) 0.112(3) 0.111(3) -0.008(2) 0.031(2) -0.022(2) C34 0.086(3) 0.080(2) 0.089(2) -0.0060(17) 0.0195(19) -0.025(2) C35 0.068(2) 0.087(2) 0.0539(16) 0.0009(15) -0.0139(13) -0.0329(17) C36 0.100(3) 0.096(2) 0.0604(17) -0.0008(16) -0.0158(16) -0.0452(19) C37 0.124(3) 0.115(3) 0.061(2) 0.0094(18) -0.0178(18) -0.055(2) C38 0.110(3) 0.145(3) 0.0556(18) -0.005(2) -0.0161(18) -0.051(3) C39 0.122(3) 0.122(3) 0.065(2) -0.0210(19) -0.0081(18) -0.056(2) C40 0.089(2) 0.090(2) 0.0671(19) -0.0043(16) -0.0116(16) -0.0335(19) _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 1.512(3) . ? C1 C8 1.516(3) . ? C1 C9 1.519(3) . ? C1 C5 1.587(3) . ? C2 C3 1.449(3) . ? C2 C11 1.515(3) . ? C2 C8 1.703(4) . ? C3 C4 1.369(3) . ? C3 C13 1.480(3) . ? C4 C19 1.485(3) . ? C4 C5 1.539(3) . ? C5 C6 1.526(3) . ? C5 C25 1.536(3) . ? C6 C7 1.356(3) . ? C6 C27 1.506(3) . ? C7 C8 1.483(3) . ? C7 C29 1.486(3) . ? C8 C35 1.501(3) . ? C9 C10 1.525(3) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 C12 1.513(3) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 C14 1.387(3) . ? C13 C18 1.389(3) . ? C14 C15 1.365(4) . ? C14 H14 0.9300 . ? C15 C16 1.363(4) . ? C15 H15 0.9300 . ? C16 C17 1.364(4) . ? C16 H16 0.9300 . ? C17 C18 1.410(4) . ? C17 H17 0.9300 . ? C18 H18 0.9300 . ? C19 C24 1.383(3) . ? C19 C20 1.387(3) . ? C20 C21 1.376(4) . ? C20 H20 0.9300 . ? C21 C22 1.375(4) . ? C21 H21 0.9300 . ? C22 C23 1.372(4) . ? C22 H22 0.9300 . ? C23 C24 1.382(4) . ? C23 H23 0.9300 . ? C24 H24 0.9300 . ? C25 C26 1.528(4) . ? C25 H25A 0.9700 . ? C25 H25B 0.9700 . ? C26 H26A 0.9600 . ? C26 H26B 0.9600 . ? C26 H26C 0.9600 . ? C27 C28 1.519(4) . ? C27 H27A 0.9700 . ? C27 H27B 0.9700 . ? C28 H28A 0.9600 . ? C28 H28B 0.9600 . ? C28 H28C 0.9600 . ? C29 C34 1.359(3) . ? C29 C30 1.372(3) . ? C30 C31 1.385(4) . ? C30 H30 0.9300 . ? C31 C32 1.329(4) . ? C31 H31 0.9300 . ? C32 C33 1.370(4) . ? C32 H32 0.9300 . ? C33 C34 1.384(4) . ? C33 H33 0.9300 . ? C34 H34 0.9300 . ? C35 C36 1.381(3) . ? C35 C40 1.380(3) . ? C36 C37 1.392(3) . ? C36 H36 0.9300 . ? C37 C38 1.358(4) . ? C37 H37 0.9300 . ? C38 C39 1.371(4) . ? C38 H38 0.9300 . ? C39 C40 1.380(3) . ? C39 H39 0.9300 . ? C40 H40 0.9300 . ? 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 C8 68.45(17) . . ? C2 C1 C9 119.9(2) . . ? C8 C1 C9 121.7(2) . . ? C2 C1 C5 104.69(19) . . ? C8 C1 C5 104.49(19) . . ? C9 C1 C5 123.98(19) . . ? C3 C2 C1 108.8(2) . . ? C3 C2 C11 119.9(2) . . ? C1 C2 C11 122.7(2) . . ? C3 C2 C8 115.9(2) . . ? C1 C2 C8 55.89(15) . . ? C11 C2 C8 117.6(2) . . ? C4 C3 C2 111.5(2) . . ? C4 C3 C13 125.1(2) . . ? C2 C3 C13 123.4(2) . . ? C3 C4 C19 124.8(2) . . ? C3 C4 C5 110.9(2) . . ? C19 C4 C5 123.8(2) . . ? C6 C5 C25 115.9(2) . . ? C6 C5 C4 94.10(18) . . ? C25 C5 C4 116.17(19) . . ? C6 C5 C1 103.34(18) . . ? C25 C5 C1 120.5(2) . . ? C4 C5 C1 102.82(18) . . ? C7 C6 C27 124.8(2) . . ? C7 C6 C5 110.9(2) . . ? C27 C6 C5 124.3(2) . . ? C6 C7 C8 111.8(2) . . ? C6 C7 C29 125.2(2) . . ? C8 C7 C29 122.63(19) . . ? C7 C8 C35 116.7(2) . . ? C7 C8 C1 107.07(19) . . ? C35 C8 C1 127.8(2) . . ? C7 C8 C2 118.7(2) . . ? C35 C8 C2 117.4(2) . . ? C1 C8 C2 55.66(15) . . ? C1 C9 C10 116.7(2) . . ? C1 C9 H9A 108.1 . . ? C10 C9 H9A 108.1 . . ? C1 C9 H9B 108.1 . . ? C10 C9 H9B 108.1 . . ? H9A C9 H9B 107.3 . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C2 C11 C12 112.9(2) . . ? C2 C11 H11A 109.0 . . ? C12 C11 H11A 109.0 . . ? C2 C11 H11B 109.0 . . ? C12 C11 H11B 109.0 . . ? H11A C11 H11B 107.8 . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C14 C13 C18 118.2(2) . . ? C14 C13 C3 120.6(2) . . ? C18 C13 C3 121.2(2) . . ? C15 C14 C13 121.8(3) . . ? C15 C14 H14 119.1 . . ? C13 C14 H14 119.1 . . ? C16 C15 C14 119.8(3) . . ? C16 C15 H15 120.1 . . ? C14 C15 H15 120.1 . . ? C15 C16 C17 120.8(3) . . ? C15 C16 H16 119.6 . . ? C17 C16 H16 119.6 . . ? C16 C17 C18 119.8(3) . . ? C16 C17 H17 120.1 . . ? C18 C17 H17 120.1 . . ? C13 C18 C17 119.6(3) . . ? C13 C18 H18 120.2 . . ? C17 C18 H18 120.2 . . ? C24 C19 C20 116.7(3) . . ? C24 C19 C4 122.6(3) . . ? C20 C19 C4 120.4(2) . . ? C21 C20 C19 121.5(3) . . ? C21 C20 H20 119.2 . . ? C19 C20 H20 119.2 . . ? C22 C21 C20 121.2(3) . . ? C22 C21 H21 119.4 . . ? C20 C21 H21 119.4 . . ? C23 C22 C21 117.8(3) . . ? C23 C22 H22 121.1 . . ? C21 C22 H22 121.1 . . ? C22 C23 C24 121.1(3) . . ? C22 C23 H23 119.4 . . ? C24 C23 H23 119.4 . . ? C23 C24 C19 121.5(3) . . ? C23 C24 H24 119.2 . . ? C19 C24 H24 119.2 . . ? C26 C25 C5 115.9(2) . . ? C26 C25 H25A 108.3 . . ? C5 C25 H25A 108.3 . . ? C26 C25 H25B 108.3 . . ? C5 C25 H25B 108.3 . . ? H25A C25 H25B 107.4 . . ? C25 C26 H26A 109.5 . . ? C25 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C25 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C6 C27 C28 113.7(2) . . ? C6 C27 H27A 108.8 . . ? C28 C27 H27A 108.8 . . ? C6 C27 H27B 108.8 . . ? C28 C27 H27B 108.8 . . ? H27A C27 H27B 107.7 . . ? C27 C28 H28A 109.5 . . ? C27 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C27 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C34 C29 C30 116.8(2) . . ? C34 C29 C7 122.1(2) . . ? C30 C29 C7 121.0(2) . . ? C29 C30 C31 121.6(3) . . ? C29 C30 H30 119.2 . . ? C31 C30 H30 119.2 . . ? C32 C31 C30 120.8(3) . . ? C32 C31 H31 119.6 . . ? C30 C31 H31 119.6 . . ? C31 C32 C33 119.1(3) . . ? C31 C32 H32 120.5 . . ? C33 C32 H32 120.5 . . ? C32 C33 C34 120.1(3) . . ? C32 C33 H33 119.9 . . ? C34 C33 H33 119.9 . . ? C29 C34 C33 121.6(3) . . ? C29 C34 H34 119.2 . . ? C33 C34 H34 119.2 . . ? C36 C35 C40 117.6(2) . . ? C36 C35 C8 119.2(2) . . ? C40 C35 C8 123.0(2) . . ? C35 C36 C37 120.6(3) . . ? C35 C36 H36 119.7 . . ? C37 C36 H36 119.7 . . ? C38 C37 C36 120.5(3) . . ? C38 C37 H37 119.8 . . ? C36 C37 H37 119.8 . . ? C37 C38 C39 119.8(3) . . ? C37 C38 H38 120.1 . . ? C39 C38 H38 120.1 . . ? C38 C39 C40 119.8(3) . . ? C38 C39 H39 120.1 . . ? C40 C39 H39 120.1 . . ? C39 C40 C35 121.6(3) . . ? C39 C40 H40 119.2 . . ? C35 C40 H40 119.2 . . ? 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 C8 C1 C2 C3 -109.0(2) . . . . ? C9 C1 C2 C3 135.9(2) . . . . ? C5 C1 C2 C3 -9.0(3) . . . . ? C8 C1 C2 C11 103.3(3) . . . . ? C9 C1 C2 C11 -11.8(3) . . . . ? C5 C1 C2 C11 -156.6(2) . . . . ? C9 C1 C2 C8 -115.1(2) . . . . ? C5 C1 C2 C8 100.1(2) . . . . ? C1 C2 C3 C4 3.0(3) . . . . ? C11 C2 C3 C4 151.6(2) . . . . ? C8 C2 C3 C4 -57.5(3) . . . . ? C1 C2 C3 C13 -178.7(2) . . . . ? C11 C2 C3 C13 -30.1(3) . . . . ? C8 C2 C3 C13 120.8(2) . . . . ? C2 C3 C4 C19 177.1(2) . . . . ? C13 C3 C4 C19 -1.2(4) . . . . ? C2 C3 C4 C5 4.8(3) . . . . ? C13 C3 C4 C5 -173.5(2) . . . . ? C3 C4 C5 C6 94.7(2) . . . . ? C19 C4 C5 C6 -77.7(3) . . . . ? C3 C4 C5 C25 -143.8(2) . . . . ? C19 C4 C5 C25 43.9(3) . . . . ? C3 C4 C5 C1 -10.0(3) . . . . ? C19 C4 C5 C1 177.7(2) . . . . ? C2 C1 C5 C6 -86.4(2) . . . . ? C8 C1 C5 C6 -15.4(2) . . . . ? C9 C1 C5 C6 130.6(2) . . . . ? C2 C1 C5 C25 142.2(2) . . . . ? C8 C1 C5 C25 -146.7(2) . . . . ? C9 C1 C5 C25 -0.8(4) . . . . ? C2 C1 C5 C4 11.0(2) . . . . ? C8 C1 C5 C4 82.1(2) . . . . ? C9 C1 C5 C4 -132.0(2) . . . . ? C25 C5 C6 C7 146.9(2) . . . . ? C4 C5 C6 C7 -91.4(2) . . . . ? C1 C5 C6 C7 12.8(3) . . . . ? C25 C5 C6 C27 -33.5(3) . . . . ? C4 C5 C6 C27 88.2(3) . . . . ? C1 C5 C6 C27 -167.6(2) . . . . ? C27 C6 C7 C8 175.5(2) . . . . ? C5 C6 C7 C8 -4.9(3) . . . . ? C27 C6 C7 C29 -11.3(4) . . . . ? C5 C6 C7 C29 168.2(2) . . . . ? C6 C7 C8 C35 -156.4(2) . . . . ? C29 C7 C8 C35 30.3(3) . . . . ? C6 C7 C8 C1 -5.7(3) . . . . ? C29 C7 C8 C1 -179.1(2) . . . . ? C6 C7 C8 C2 54.0(3) . . . . ? C29 C7 C8 C2 -119.4(2) . . . . ? C2 C1 C8 C7 113.5(2) . . . . ? C9 C1 C8 C7 -133.8(2) . . . . ? C5 C1 C8 C7 13.1(3) . . . . ? C2 C1 C8 C35 -100.2(3) . . . . ? C9 C1 C8 C35 12.6(4) . . . . ? C5 C1 C8 C35 159.5(3) . . . . ? C9 C1 C8 C2 112.7(3) . . . . ? C5 C1 C8 C2 -100.3(2) . . . . ? C3 C2 C8 C7 4.2(3) . . . . ? C1 C2 C8 C7 -91.8(2) . . . . ? C11 C2 C8 C7 155.8(2) . . . . ? C3 C2 C8 C35 -145.2(2) . . . . ? C1 C2 C8 C35 118.8(2) . . . . ? C11 C2 C8 C35 6.4(3) . . . . ? C3 C2 C8 C1 96.0(2) . . . . ? C11 C2 C8 C1 -112.4(3) . . . . ? C2 C1 C9 C10 166.2(2) . . . . ? C8 C1 C9 C10 84.4(3) . . . . ? C5 C1 C9 C10 -56.0(3) . . . . ? C3 C2 C11 C12 -59.8(3) . . . . ? C1 C2 C11 C12 84.4(3) . . . . ? C8 C2 C11 C12 149.8(2) . . . . ? C4 C3 C13 C14 -48.9(4) . . . . ? C2 C3 C13 C14 133.0(3) . . . . ? C4 C3 C13 C18 132.0(3) . . . . ? C2 C3 C13 C18 -46.0(4) . . . . ? C18 C13 C14 C15 1.8(4) . . . . ? C3 C13 C14 C15 -177.2(3) . . . . ? C13 C14 C15 C16 -1.4(5) . . . . ? C14 C15 C16 C17 0.3(5) . . . . ? C15 C16 C17 C18 0.3(5) . . . . ? C14 C13 C18 C17 -1.2(4) . . . . ? C3 C13 C18 C17 177.8(3) . . . . ? C16 C17 C18 C13 0.2(5) . . . . ? C3 C4 C19 C24 112.2(3) . . . . ? C5 C4 C19 C24 -76.4(3) . . . . ? C3 C4 C19 C20 -61.2(4) . . . . ? C5 C4 C19 C20 110.1(3) . . . . ? C24 C19 C20 C21 1.3(4) . . . . ? C4 C19 C20 C21 175.1(3) . . . . ? C19 C20 C21 C22 -2.6(5) . . . . ? C20 C21 C22 C23 2.6(6) . . . . ? C21 C22 C23 C24 -1.5(6) . . . . ? C22 C23 C24 C19 0.3(5) . . . . ? C20 C19 C24 C23 -0.2(4) . . . . ? C4 C19 C24 C23 -173.9(3) . . . . ? C6 C5 C25 C26 176.3(2) . . . . ? C4 C5 C25 C26 67.2(3) . . . . ? C1 C5 C25 C26 -58.0(3) . . . . ? C7 C6 C27 C28 -85.7(3) . . . . ? C5 C6 C27 C28 94.8(3) . . . . ? C6 C7 C29 C34 94.4(3) . . . . ? C8 C7 C29 C34 -93.2(3) . . . . ? C6 C7 C29 C30 -85.8(3) . . . . ? C8 C7 C29 C30 86.7(3) . . . . ? C34 C29 C30 C31 -0.4(4) . . . . ? C7 C29 C30 C31 179.7(3) . . . . ? C29 C30 C31 C32 0.8(5) . . . . ? C30 C31 C32 C33 -1.0(5) . . . . ? C31 C32 C33 C34 0.9(5) . . . . ? C30 C29 C34 C33 0.3(4) . . . . ? C7 C29 C34 C33 -179.9(3) . . . . ? C32 C33 C34 C29 -0.5(5) . . . . ? C7 C8 C35 C36 -85.4(3) . . . . ? C1 C8 C35 C36 130.9(3) . . . . ? C2 C8 C35 C36 64.6(3) . . . . ? C7 C8 C35 C40 88.9(3) . . . . ? C1 C8 C35 C40 -54.7(4) . . . . ? C2 C8 C35 C40 -121.0(3) . . . . ? C40 C35 C36 C37 0.0(4) . . . . ? C8 C35 C36 C37 174.7(3) . . . . ? C35 C36 C37 C38 -0.1(5) . . . . ? C36 C37 C38 C39 -0.4(5) . . . . ? C37 C38 C39 C40 1.0(5) . . . . ? C38 C39 C40 C35 -1.1(5) . . . . ? C36 C35 C40 C39 0.6(4) . . . . ? C8 C35 C40 C39 -173.9(3) . . . . ? _diffrn_measured_fraction_theta_max 0.962 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.962 _refine_diff_density_max 0.179 _refine_diff_density_min -0.140 _refine_diff_density_rms 0.030 _database_code_depnum_ccdc_archive 'CCDC 966203' ####################################################################### # # 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_a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C32 H56' _chemical_formula_weight 440.77 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' _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 35.265(7) _cell_length_b 19.026(4) _cell_length_c 21.174(4) _cell_angle_alpha 90.00 _cell_angle_beta 122.27(3) _cell_angle_gamma 90.00 _cell_volume 12012(4) _cell_formula_units_Z 16 _cell_measurement_temperature 143(2) _cell_measurement_reflns_used 22640 _cell_measurement_theta_min 1.93 _cell_measurement_theta_max 25.03 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 0.975 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3968 _exptl_absorpt_coefficient_mu 0.054 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.973 _exptl_absorpt_correction_T_max 0.987 _exptl_absorpt_process_details ; HIGASHI, T. (1995). Abscor-Empirical Absorption Correction based on Fourier Series Approximation. Rigaku Corporation,Tokyo,Japan. ; _diffrn_ambient_temperature 143(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 'Rigaku RAXIS RAPID IP' _diffrn_measurement_method \W _diffrn_detector_area_resol_mean 10.00 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 22640 _diffrn_reflns_av_R_equivalents 0.0382 _diffrn_reflns_av_sigmaI/netI 0.1049 _diffrn_reflns_limit_h_min -41 _diffrn_reflns_limit_h_max 41 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.93 _diffrn_reflns_theta_max 25.03 _reflns_number_total 10249 _reflns_number_gt 5201 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Rapid-AUTO (Rigaku,2000)' _computing_cell_refinement Rapid-AUTO _computing_data_reduction 'CrystalStructure (Rigaku/MSC,2000)' _computing_structure_solution SHELXS-97,(Sheldrick,1997) _computing_structure_refinement SHELXL-97,(Sheldrick,1997) _computing_molecular_graphics 'Siemens SHELXTL V4.2,(Sheldrick,1990)' _computing_publication_material SHELXL-97,(Sheldrick,1997) _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0450P)^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 constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.00134(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 10249 _refine_ls_number_parameters 578 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1197 _refine_ls_R_factor_gt 0.0548 _refine_ls_wR_factor_ref 0.1208 _refine_ls_wR_factor_gt 0.1098 _refine_ls_goodness_of_fit_ref 0.987 _refine_ls_restrained_S_all 0.987 _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 0.08579(7) 0.70119(12) 0.48296(13) 0.0340(6) Uani 1 1 d . . . C2 C 0.09694(7) 0.76877(11) 0.52309(12) 0.0269(6) Uani 1 1 d . . . C3 C 0.14165(7) 0.77430(12) 0.57354(12) 0.0296(6) Uani 1 1 d . . . C4 C 0.16651(7) 0.71365(11) 0.56418(12) 0.0237(5) Uani 1 1 d . . . C5 C 0.17335(8) 0.74702(12) 0.50443(13) 0.0323(6) Uani 1 1 d . . . C6 C 0.14084(7) 0.72689(11) 0.43524(12) 0.0267(6) Uani 1 1 d . . . C7 C 0.11134(7) 0.67509(12) 0.43841(12) 0.0301(6) Uani 1 1 d . . . C8 C 0.12868(7) 0.65863(11) 0.51926(12) 0.0248(5) Uani 1 1 d . . . C9 C 0.04010(7) 0.66868(13) 0.45625(12) 0.0358(6) Uani 1 1 d . . . H9A H 0.0428 0.6180 0.4553 0.043 Uiso 1 1 calc R . . H9B H 0.0321 0.6795 0.4925 0.043 Uiso 1 1 calc R . . C10 C 0.00197(7) 0.69255(13) 0.37968(13) 0.0395(7) Uani 1 1 d . . . H10A H -0.0014 0.7431 0.3800 0.047 Uiso 1 1 calc R . . H10B H 0.0093 0.6814 0.3427 0.047 Uiso 1 1 calc R . . C11 C -0.04202(7) 0.65730(14) 0.35815(14) 0.0523(8) Uani 1 1 d . . . H11A H -0.0653 0.6733 0.3096 0.078 Uiso 1 1 calc R . . H11B H -0.0496 0.6690 0.3941 0.078 Uiso 1 1 calc R . . H11C H -0.0389 0.6073 0.3571 0.078 Uiso 1 1 calc R . . C12 C 0.06269(7) 0.82422(12) 0.50893(13) 0.0330(6) Uani 1 1 d . . . H12A H 0.0729 0.8496 0.5551 0.040 Uiso 1 1 calc R . . H12B H 0.0347 0.8011 0.4950 0.040 Uiso 1 1 calc R . . C13 C 0.05358(8) 0.87691(12) 0.44822(13) 0.0384(6) Uani 1 1 d . . . H13A H 0.0810 0.9023 0.4632 0.046 Uiso 1 1 calc R . . H13B H 0.0447 0.8517 0.4025 0.046 Uiso 1 1 calc R . . C14 C 0.01705(8) 0.92924(13) 0.43316(15) 0.0495(8) Uani 1 1 d . . . H14A H 0.0126 0.9614 0.3948 0.074 Uiso 1 1 calc R . . H14B H 0.0259 0.9549 0.4781 0.074 Uiso 1 1 calc R . . H14C H -0.0104 0.9045 0.4171 0.074 Uiso 1 1 calc R . . C15 C 0.16473(7) 0.83292(12) 0.62916(12) 0.0323(6) Uani 1 1 d . . . H15A H 0.1479 0.8761 0.6083 0.039 Uiso 1 1 calc R . . H15B H 0.1944 0.8399 0.6378 0.039 Uiso 1 1 calc R . . C16 C 0.16909(8) 0.81815(13) 0.70336(13) 0.0423(7) Uani 1 1 d . . . H16A H 0.1394 0.8158 0.6955 0.051 Uiso 1 1 calc R . . H16B H 0.1833 0.7728 0.7219 0.051 Uiso 1 1 calc R . . C17 C 0.19631(8) 0.87399(14) 0.76163(13) 0.0519(8) Uani 1 1 d . . . H17A H 0.1982 0.8625 0.8074 0.078 Uiso 1 1 calc R . . H17B H 0.1820 0.9189 0.7441 0.078 Uiso 1 1 calc R . . H17C H 0.2259 0.8760 0.7703 0.078 Uiso 1 1 calc R . . C18 C 0.20986(7) 0.68734(11) 0.63318(12) 0.0264(5) Uani 1 1 d . . . H18A H 0.2267 0.7275 0.6634 0.032 Uiso 1 1 calc R . . H18B H 0.2022 0.6586 0.6627 0.032 Uiso 1 1 calc R . . C19 C 0.23971(7) 0.64458(11) 0.61564(12) 0.0301(6) Uani 1 1 d . . . H19A H 0.2218 0.6083 0.5797 0.036 Uiso 1 1 calc R . . H19B H 0.2511 0.6751 0.5928 0.036 Uiso 1 1 calc R . . C20 C 0.27901(8) 0.61034(13) 0.68430(13) 0.0474(7) Uani 1 1 d . . . H20A H 0.2964 0.5839 0.6700 0.071 Uiso 1 1 calc R . . H20B H 0.2680 0.5795 0.7068 0.071 Uiso 1 1 calc R . . H20C H 0.2975 0.6460 0.7195 0.071 Uiso 1 1 calc R . . C21 C 0.20917(7) 0.80199(11) 0.52425(12) 0.0305(6) Uani 1 1 d . . . H21A H 0.2256 0.7884 0.5014 0.037 Uiso 1 1 calc R . . H21B H 0.2301 0.8010 0.5779 0.037 Uiso 1 1 calc R . . C22 C 0.19338(8) 0.87739(12) 0.50154(13) 0.0345(6) Uani 1 1 d . . . H22A H 0.1768 0.8811 0.4475 0.041 Uiso 1 1 calc R . . H22B H 0.1733 0.8898 0.5179 0.041 Uiso 1 1 calc R . . C23 C 0.23246(9) 0.92882(13) 0.53510(14) 0.0509(8) Uani 1 1 d . . . H23A H 0.2212 0.9758 0.5200 0.076 Uiso 1 1 calc R . . H23B H 0.2520 0.9175 0.5179 0.076 Uiso 1 1 calc R . . H23C H 0.2488 0.9256 0.5886 0.076 Uiso 1 1 calc R . . C24 C 0.13308(7) 0.75538(12) 0.36281(12) 0.0315(6) Uani 1 1 d . . . H24A H 0.1282 0.7164 0.3297 0.038 Uiso 1 1 calc R . . H24B H 0.1598 0.7801 0.3728 0.038 Uiso 1 1 calc R . . C25 C 0.09296(8) 0.80537(13) 0.32341(12) 0.0369(6) Uani 1 1 d . . . H25A H 0.0660 0.7800 0.3110 0.044 Uiso 1 1 calc R . . H25B H 0.0971 0.8430 0.3574 0.044 Uiso 1 1 calc R . . C26 C 0.08681(8) 0.83677(13) 0.25311(13) 0.0482(7) Uani 1 1 d . . . H26A H 0.0613 0.8676 0.2307 0.072 Uiso 1 1 calc R . . H26B H 0.0820 0.7998 0.2187 0.072 Uiso 1 1 calc R . . H26C H 0.1132 0.8628 0.2652 0.072 Uiso 1 1 calc R . . C27 C 0.08938(7) 0.62004(12) 0.37741(12) 0.0333(6) Uani 1 1 d . . . H27A H 0.0729 0.6432 0.3292 0.040 Uiso 1 1 calc R . . H27B H 0.0681 0.5933 0.3835 0.040 Uiso 1 1 calc R . . C28 C 0.12360(8) 0.56993(12) 0.37895(13) 0.0398(7) Uani 1 1 d . . . H28A H 0.1448 0.5969 0.3728 0.048 Uiso 1 1 calc R . . H28B H 0.1402 0.5473 0.4275 0.048 Uiso 1 1 calc R . . C29 C 0.10284(9) 0.51401(13) 0.31913(15) 0.0572(8) Uani 1 1 d . . . H29A H 0.1260 0.4841 0.3233 0.086 Uiso 1 1 calc R . . H29B H 0.0872 0.5359 0.2708 0.086 Uiso 1 1 calc R . . H29C H 0.0822 0.4865 0.3252 0.086 Uiso 1 1 calc R . . C30 C 0.13049(7) 0.58606(11) 0.55034(12) 0.0288(6) Uani 1 1 d . . . H30A H 0.1602 0.5665 0.5702 0.035 Uiso 1 1 calc R . . H30B H 0.1092 0.5559 0.5099 0.035 Uiso 1 1 calc R . . C31 C 0.12009(8) 0.58563(12) 0.61182(13) 0.0316(6) Uani 1 1 d . . . H31A H 0.1403 0.6177 0.6512 0.038 Uiso 1 1 calc R . . H31B H 0.0897 0.6025 0.5914 0.038 Uiso 1 1 calc R . . C32 C 0.12463(9) 0.51318(13) 0.64496(14) 0.0530(8) Uani 1 1 d . . . H32A H 0.1179 0.5157 0.6832 0.079 Uiso 1 1 calc R . . H32B H 0.1548 0.4965 0.6661 0.079 Uiso 1 1 calc R . . H32C H 0.1041 0.4815 0.6065 0.079 Uiso 1 1 calc R . . C33 C 0.16717(8) 0.81612(13) 1.03718(13) 0.0378(6) Uani 1 1 d . . . C34 C 0.15512(7) 0.80646(12) 0.96396(13) 0.0320(6) Uani 1 1 d . . . C35 C 0.13564(12) 0.74046(14) 0.93801(15) 0.0688(10) Uani 1 1 d . . . C36 C 0.13609(7) 0.70008(12) 1.00018(12) 0.0292(6) Uani 1 1 d . . . C37 C 0.08656(7) 0.71456(12) 0.95195(13) 0.0374(6) Uani 1 1 d . . . C38 C 0.07553(7) 0.77203(12) 0.98047(12) 0.0293(6) Uani 1 1 d . . . C39 C 0.11262(9) 0.79743(15) 1.04462(14) 0.0589(9) Uani 1 1 d . . . C40 C 0.15338(7) 0.75459(12) 1.06477(12) 0.0283(6) Uani 1 1 d . . . C41 C 0.20060(7) 0.87124(12) 1.08831(13) 0.0380(6) Uani 1 1 d . . . H41A H 0.1966 0.8800 1.1295 0.046 Uiso 1 1 calc R . . H41B H 0.1948 0.9148 1.0608 0.046 Uiso 1 1 calc R . . C42 C 0.24883(7) 0.84864(13) 1.11921(13) 0.0383(6) Uani 1 1 d . . . H42A H 0.2546 0.8052 1.1469 0.046 Uiso 1 1 calc R . . H42B H 0.2527 0.8395 1.0780 0.046 Uiso 1 1 calc R . . C43 C 0.28254(8) 0.90378(13) 1.16997(14) 0.0494(8) Uani 1 1 d . . . H43A H 0.3124 0.8874 1.1877 0.074 Uiso 1 1 calc R . . H43B H 0.2794 0.9121 1.2117 0.074 Uiso 1 1 calc R . . H43C H 0.2772 0.9467 1.1426 0.074 Uiso 1 1 calc R . . C44 C 0.16039(8) 0.86205(12) 0.91797(13) 0.0386(7) Uani 1 1 d . . . H44A H 0.1609 0.8393 0.8774 0.046 Uiso 1 1 calc R . . H44B H 0.1890 0.8854 0.9492 0.046 Uiso 1 1 calc R . . C45 C 0.12313(8) 0.91733(12) 0.88522(13) 0.0372(6) Uani 1 1 d . . . H45A H 0.0945 0.8939 0.8542 0.045 Uiso 1 1 calc R . . H45B H 0.1227 0.9403 0.9258 0.045 Uiso 1 1 calc R . . C46 C 0.12841(9) 0.97305(13) 0.83871(14) 0.0484(7) Uani 1 1 d . . . H46A H 0.1039 1.0057 0.8195 0.073 Uiso 1 1 calc R . . H46B H 0.1284 0.9509 0.7980 0.073 Uiso 1 1 calc R . . H46C H 0.1562 0.9976 0.8694 0.073 Uiso 1 1 calc R . . C47 C 0.13123(9) 0.70620(13) 0.86963(13) 0.0449(7) Uani 1 1 d . . . H47A H 0.1586 0.7149 0.8705 0.054 Uiso 1 1 calc R . . H47B H 0.1287 0.6558 0.8733 0.054 Uiso 1 1 calc R . . C48 C 0.09187(8) 0.73063(13) 0.79498(13) 0.0438(7) Uani 1 1 d . . . H48A H 0.0643 0.7231 0.7939 0.053 Uiso 1 1 calc R . . H48B H 0.0947 0.7807 0.7896 0.053 Uiso 1 1 calc R . . C49 C 0.08898(8) 0.69217(13) 0.72979(13) 0.0451(7) Uani 1 1 d . . . H49A H 0.0637 0.7094 0.6838 0.068 Uiso 1 1 calc R . . H49B H 0.0854 0.6427 0.7342 0.068 Uiso 1 1 calc R . . H49C H 0.1160 0.7001 0.7301 0.068 Uiso 1 1 calc R . . C50 C 0.15564(7) 0.62641(12) 1.01694(12) 0.0295(6) Uani 1 1 d . . . H50A H 0.1361 0.5961 0.9750 0.035 Uiso 1 1 calc R . . H50B H 0.1562 0.6085 1.0604 0.035 Uiso 1 1 calc R . . C51 C 0.20301(7) 0.62271(12) 1.03160(13) 0.0332(6) Uani 1 1 d . . . H51A H 0.2019 0.6340 0.9860 0.040 Uiso 1 1 calc R . . H51B H 0.2217 0.6575 1.0689 0.040 Uiso 1 1 calc R . . C52 C 0.22388(8) 0.55098(12) 1.05846(15) 0.0444(7) Uani 1 1 d . . . H52A H 0.2536 0.5511 1.0674 0.067 Uiso 1 1 calc R . . H52B H 0.2060 0.5165 1.0211 0.067 Uiso 1 1 calc R . . H52C H 0.2254 0.5397 1.1039 0.067 Uiso 1 1 calc R . . C53 C 0.05260(7) 0.66050(12) 0.90036(13) 0.0378(6) Uani 1 1 d . . . H53A H 0.0650 0.6335 0.8767 0.045 Uiso 1 1 calc R . . H53B H 0.0260 0.6843 0.8614 0.045 Uiso 1 1 calc R . . C54 C 0.03972(8) 0.61090(14) 0.94231(14) 0.0475(7) Uani 1 1 d . . . H54A H 0.0668 0.5906 0.9840 0.057 Uiso 1 1 calc R . . H54B H 0.0252 0.6378 0.9625 0.057 Uiso 1 1 calc R . . C55 C 0.00885(9) 0.55222(14) 0.89479(16) 0.0644(9) Uani 1 1 d . . . H55A H 0.0019 0.5233 0.9245 0.097 Uiso 1 1 calc R . . H55B H 0.0233 0.5243 0.8758 0.097 Uiso 1 1 calc R . . H55C H -0.0183 0.5717 0.8538 0.097 Uiso 1 1 calc R . . C56 C 0.02900(7) 0.80377(12) 0.94231(13) 0.0345(6) Uani 1 1 d . . . H56A H 0.0266 0.8310 0.9788 0.041 Uiso 1 1 calc R . . H56B H 0.0073 0.7659 0.9254 0.041 Uiso 1 1 calc R . . C57 C 0.01692(8) 0.85055(13) 0.87643(13) 0.0406(7) Uani 1 1 d . . . H57A H 0.0171 0.8227 0.8382 0.049 Uiso 1 1 calc R . . H57B H 0.0397 0.8866 0.8923 0.049 Uiso 1 1 calc R . . C58 C -0.02884(7) 0.88581(13) 0.84243(13) 0.0449(7) Uani 1 1 d . . . H58A H -0.0344 0.9150 0.8014 0.067 Uiso 1 1 calc R . . H58B H -0.0292 0.9141 0.8796 0.067 Uiso 1 1 calc R . . H58C H -0.0517 0.8505 0.8249 0.067 Uiso 1 1 calc R . . C59 C 0.11052(8) 0.84968(12) 1.09694(12) 0.0361(6) Uani 1 1 d . . . H59A H 0.1386 0.8472 1.1450 0.043 Uiso 1 1 calc R . . H59B H 0.0869 0.8350 1.1045 0.043 Uiso 1 1 calc R . . C60 C 0.10222(8) 0.92586(12) 1.07144(13) 0.0354(6) Uani 1 1 d . . . H60A H 0.1233 0.9394 1.0575 0.042 Uiso 1 1 calc R . . H60B H 0.0722 0.9302 1.0275 0.042 Uiso 1 1 calc R . . C61 C 0.10702(8) 0.97564(12) 1.13135(13) 0.0419(7) Uani 1 1 d . . . H61A H 0.1013 1.0229 1.1126 0.063 Uiso 1 1 calc R . . H61B H 0.1369 0.9725 1.1746 0.063 Uiso 1 1 calc R . . H61C H 0.0859 0.9630 1.1448 0.063 Uiso 1 1 calc R . . C62 C 0.18200(7) 0.72872(12) 1.14531(12) 0.0301(6) Uani 1 1 d . . . H62A H 0.1972 0.7687 1.1776 0.036 Uiso 1 1 calc R . . H62B H 0.2048 0.6971 1.1494 0.036 Uiso 1 1 calc R . . C63 C 0.15537(7) 0.69063(12) 1.17320(12) 0.0310(6) Uani 1 1 d . . . H63A H 0.1350 0.7238 1.1748 0.037 Uiso 1 1 calc R . . H63B H 0.1374 0.6540 1.1378 0.037 Uiso 1 1 calc R . . C64 C 0.18454(8) 0.65809(14) 1.24962(13) 0.0461(7) Uani 1 1 d . . . H64A H 0.1660 0.6348 1.2636 0.069 Uiso 1 1 calc R . . H64B H 0.2017 0.6942 1.2854 0.069 Uiso 1 1 calc R . . H64C H 0.2045 0.6247 1.2484 0.069 Uiso 1 1 calc R . . 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 0.0203(13) 0.0264(14) 0.0455(15) 0.0018(12) 0.0109(12) 0.0003(11) C2 0.0276(14) 0.0224(13) 0.0364(14) 0.0029(12) 0.0209(12) 0.0054(11) C3 0.0264(14) 0.0208(13) 0.0424(15) -0.0037(12) 0.0189(12) 0.0015(11) C4 0.0217(12) 0.0200(13) 0.0319(13) 0.0005(11) 0.0160(11) 0.0018(10) C5 0.0315(14) 0.0275(14) 0.0380(15) 0.0012(12) 0.0187(13) -0.0045(12) C6 0.0259(13) 0.0245(13) 0.0336(15) 0.0014(12) 0.0186(12) 0.0029(11) C7 0.0299(13) 0.0279(14) 0.0347(15) -0.0021(12) 0.0188(12) -0.0017(12) C8 0.0238(13) 0.0203(13) 0.0322(14) 0.0008(11) 0.0162(11) 0.0033(11) C9 0.0237(13) 0.0305(15) 0.0504(17) -0.0007(13) 0.0178(12) 0.0005(12) C10 0.0249(14) 0.0404(16) 0.0487(16) 0.0043(14) 0.0166(12) 0.0033(13) C11 0.0254(14) 0.0553(19) 0.0610(19) 0.0025(16) 0.0128(13) -0.0045(14) C12 0.0261(13) 0.0276(14) 0.0475(15) -0.0025(12) 0.0212(12) 0.0045(11) C13 0.0318(14) 0.0318(15) 0.0515(17) 0.0064(13) 0.0221(13) 0.0087(12) C14 0.0380(16) 0.0345(17) 0.0649(19) 0.0016(14) 0.0200(14) 0.0128(13) C15 0.0270(13) 0.0289(14) 0.0437(15) 0.0008(12) 0.0206(12) 0.0040(12) C16 0.0388(15) 0.0416(17) 0.0544(18) -0.0005(14) 0.0302(14) 0.0024(14) C17 0.0495(17) 0.061(2) 0.0442(17) -0.0037(16) 0.0243(14) 0.0146(16) C18 0.0251(13) 0.0219(13) 0.0337(14) 0.0026(11) 0.0166(11) 0.0029(11) C19 0.0256(13) 0.0237(14) 0.0413(15) 0.0023(12) 0.0181(12) 0.0027(11) C20 0.0333(15) 0.0478(18) 0.0519(17) -0.0015(14) 0.0166(13) 0.0157(14) C21 0.0296(13) 0.0278(14) 0.0396(15) 0.0000(12) 0.0221(12) -0.0010(12) C22 0.0389(15) 0.0252(14) 0.0450(16) 0.0019(12) 0.0261(13) -0.0008(12) C23 0.0637(19) 0.0303(16) 0.0643(19) -0.0032(15) 0.0379(16) -0.0105(15) C24 0.0328(14) 0.0304(14) 0.0343(15) -0.0004(12) 0.0199(12) -0.0029(12) C25 0.0389(15) 0.0339(15) 0.0401(15) 0.0066(13) 0.0226(13) 0.0012(13) C26 0.0568(18) 0.0393(17) 0.0455(17) 0.0091(14) 0.0254(15) 0.0009(15) C27 0.0331(14) 0.0311(15) 0.0385(15) 0.0007(12) 0.0209(12) 0.0000(12) C28 0.0429(16) 0.0342(16) 0.0473(17) 0.0048(13) 0.0274(14) 0.0078(13) C29 0.079(2) 0.0402(18) 0.068(2) -0.0051(16) 0.0493(18) 0.0077(16) C30 0.0285(13) 0.0246(13) 0.0350(14) 0.0017(11) 0.0182(12) 0.0021(11) C31 0.0314(14) 0.0309(14) 0.0376(14) 0.0005(12) 0.0219(12) -0.0009(12) C32 0.080(2) 0.0347(17) 0.0611(19) 0.0032(15) 0.0491(17) -0.0071(15) C33 0.0388(15) 0.0358(16) 0.0375(16) -0.0040(13) 0.0194(12) -0.0161(13) C34 0.0309(14) 0.0242(14) 0.0436(16) 0.0044(13) 0.0217(12) 0.0022(12) C35 0.143(3) 0.0260(16) 0.0478(19) -0.0005(15) 0.058(2) 0.0064(19) C36 0.0254(13) 0.0240(13) 0.0369(15) 0.0003(12) 0.0158(12) 0.0036(11) C37 0.0245(14) 0.0313(15) 0.0524(17) -0.0116(13) 0.0178(13) -0.0022(12) C38 0.0259(13) 0.0292(14) 0.0311(14) -0.0019(12) 0.0140(12) 0.0012(12) C39 0.0542(19) 0.055(2) 0.0397(17) -0.0114(15) 0.0066(15) 0.0326(16) C40 0.0242(13) 0.0242(14) 0.0339(14) 0.0004(12) 0.0139(11) 0.0023(11) C41 0.0352(15) 0.0332(15) 0.0459(16) 0.0047(13) 0.0219(13) -0.0054(13) C42 0.0346(15) 0.0367(16) 0.0480(16) -0.0003(13) 0.0250(13) -0.0055(13) C43 0.0278(15) 0.0450(18) 0.0640(19) 0.0061(15) 0.0169(14) -0.0012(13) C44 0.0423(15) 0.0357(16) 0.0428(16) 0.0053(13) 0.0260(13) 0.0031(13) C45 0.0412(15) 0.0333(15) 0.0398(16) 0.0076(13) 0.0235(13) 0.0082(13) C46 0.0493(17) 0.0397(17) 0.0578(18) 0.0099(15) 0.0295(15) 0.0014(14) C47 0.0630(19) 0.0343(16) 0.0398(16) 0.0050(13) 0.0290(15) 0.0134(14) C48 0.0494(17) 0.0411(17) 0.0503(18) 0.0045(14) 0.0329(15) 0.0117(14) C49 0.0454(16) 0.0431(17) 0.0419(16) -0.0026(14) 0.0200(13) 0.0030(14) C50 0.0278(13) 0.0263(14) 0.0365(14) -0.0004(11) 0.0185(12) 0.0000(11) C51 0.0295(14) 0.0293(14) 0.0459(16) 0.0008(12) 0.0235(12) 0.0042(12) C52 0.0295(14) 0.0298(15) 0.0718(19) -0.0054(14) 0.0256(14) 0.0035(12) C53 0.0251(13) 0.0328(15) 0.0508(16) -0.0099(13) 0.0172(12) 0.0011(12) C54 0.0343(15) 0.0468(18) 0.0605(19) -0.0028(15) 0.0248(14) -0.0041(14) C55 0.0433(18) 0.0392(18) 0.103(3) -0.0003(17) 0.0340(18) -0.0071(15) C56 0.0277(14) 0.0318(15) 0.0431(15) -0.0015(13) 0.0184(12) 0.0042(12) C57 0.0338(15) 0.0406(16) 0.0457(16) 0.0031(14) 0.0200(13) 0.0131(13) C58 0.0331(15) 0.0391(17) 0.0517(17) 0.0013(14) 0.0155(13) 0.0097(13) C59 0.0320(14) 0.0321(15) 0.0370(15) -0.0032(12) 0.0136(12) 0.0074(12) C60 0.0305(14) 0.0320(15) 0.0474(16) 0.0036(13) 0.0233(13) 0.0043(12) C61 0.0385(15) 0.0256(15) 0.0573(18) -0.0047(14) 0.0227(14) 0.0001(13) C62 0.0225(13) 0.0275(14) 0.0394(15) 0.0020(12) 0.0160(12) 0.0019(11) C63 0.0297(14) 0.0245(14) 0.0440(15) 0.0023(12) 0.0230(12) 0.0010(11) C64 0.0417(16) 0.0531(18) 0.0471(17) 0.0073(15) 0.0262(14) -0.0040(15) _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 1.474(3) . ? C1 C8 1.514(3) . ? C1 C9 1.525(3) . ? C1 C7 1.690(3) . ? C2 C3 1.356(3) . ? C2 C12 1.508(3) . ? C3 C15 1.506(3) . ? C3 C4 1.525(3) . ? C4 C18 1.529(3) . ? C4 C5 1.545(3) . ? C4 C8 1.557(3) . ? C5 C6 1.347(3) . ? C5 C21 1.516(3) . ? C6 C7 1.460(3) . ? C6 C24 1.507(3) . ? C7 C8 1.511(3) . ? C7 C27 1.516(3) . ? C8 C30 1.516(3) . ? C9 C10 1.521(3) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C11 1.519(3) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 C13 1.523(3) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C14 1.521(3) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 C16 1.521(3) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 C17 1.519(3) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 C19 1.525(3) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 C20 1.519(3) . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C21 C22 1.521(3) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C22 C23 1.522(3) . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? C24 C25 1.530(3) . ? C24 H24A 0.9700 . ? C24 H24B 0.9700 . ? C25 C26 1.508(3) . ? C25 H25A 0.9700 . ? C25 H25B 0.9700 . ? C26 H26A 0.9600 . ? C26 H26B 0.9600 . ? C26 H26C 0.9600 . ? C27 C28 1.525(3) . ? C27 H27A 0.9700 . ? C27 H27B 0.9700 . ? C28 C29 1.511(3) . ? C28 H28A 0.9700 . ? C28 H28B 0.9700 . ? C29 H29A 0.9600 . ? C29 H29B 0.9600 . ? C29 H29C 0.9600 . ? C30 C31 1.529(3) . ? C30 H30A 0.9700 . ? C30 H30B 0.9700 . ? C31 C32 1.516(3) . ? C31 H31A 0.9700 . ? C31 H31B 0.9700 . ? C32 H32A 0.9600 . ? C32 H32B 0.9600 . ? C32 H32C 0.9600 . ? C33 C34 1.384(3) . ? C33 C40 1.501(3) . ? C33 C41 1.516(3) . ? C34 C35 1.396(3) . ? C34 C44 1.515(3) . ? C35 C36 1.517(3) . ? C35 C47 1.518(3) . ? C35 C37 1.968(4) . ? C36 C37 1.505(3) . ? C36 C50 1.518(3) . ? C36 C40 1.558(3) . ? C37 C38 1.401(3) . ? C37 C53 1.513(3) . ? C38 C39 1.375(3) . ? C38 C56 1.515(3) . ? C39 C40 1.503(3) . ? C39 C59 1.519(3) . ? C40 C62 1.527(3) . ? C41 C42 1.522(3) . ? C41 H41A 0.9700 . ? C41 H41B 0.9700 . ? C42 C43 1.518(3) . ? C42 H42A 0.9700 . ? C42 H42B 0.9700 . ? C43 H43A 0.9600 . ? C43 H43B 0.9600 . ? C43 H43C 0.9600 . ? C44 C45 1.530(3) . ? C44 H44A 0.9700 . ? C44 H44B 0.9700 . ? C45 C46 1.524(3) . ? C45 H45A 0.9700 . ? C45 H45B 0.9700 . ? C46 H46A 0.9600 . ? C46 H46B 0.9600 . ? C46 H46C 0.9600 . ? C47 C48 1.516(3) . ? C47 H47A 0.9700 . ? C47 H47B 0.9700 . ? C48 C49 1.517(3) . ? C48 H48A 0.9700 . ? C48 H48B 0.9700 . ? C49 H49A 0.9600 . ? C49 H49B 0.9600 . ? C49 H49C 0.9600 . ? C50 C51 1.529(3) . ? C50 H50A 0.9700 . ? C50 H50B 0.9700 . ? C51 C52 1.510(3) . ? C51 H51A 0.9700 . ? C51 H51B 0.9700 . ? C52 H52A 0.9600 . ? C52 H52B 0.9600 . ? C52 H52C 0.9600 . ? C53 C54 1.522(3) . ? C53 H53A 0.9700 . ? C53 H53B 0.9700 . ? C54 C55 1.508(3) . ? C54 H54A 0.9700 . ? C54 H54B 0.9700 . ? C55 H55A 0.9600 . ? C55 H55B 0.9600 . ? C55 H55C 0.9600 . ? C56 C57 1.512(3) . ? C56 H56A 0.9700 . ? C56 H56B 0.9700 . ? C57 C58 1.527(3) . ? C57 H57A 0.9700 . ? C57 H57B 0.9700 . ? C58 H58A 0.9600 . ? C58 H58B 0.9600 . ? C58 H58C 0.9600 . ? C59 C60 1.520(3) . ? C59 H59A 0.9700 . ? C59 H59B 0.9700 . ? C60 C61 1.518(3) . ? C60 H60A 0.9700 . ? C60 H60B 0.9700 . ? C61 H61A 0.9600 . ? C61 H61B 0.9600 . ? C61 H61C 0.9600 . ? C62 C63 1.533(3) . ? C62 H62A 0.9700 . ? C62 H62B 0.9700 . ? C63 C64 1.511(3) . ? C63 H63A 0.9700 . ? C63 H63B 0.9700 . ? C64 H64A 0.9600 . ? C64 H64B 0.9600 . ? C64 H64C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C8 106.69(18) . . ? C2 C1 C9 118.1(2) . . ? C8 C1 C9 122.9(2) . . ? C2 C1 C7 121.36(19) . . ? C8 C1 C7 55.97(13) . . ? C9 C1 C7 116.52(19) . . ? C3 C2 C1 111.20(19) . . ? C3 C2 C12 125.0(2) . . ? C1 C2 C12 123.82(19) . . ? C2 C3 C15 126.1(2) . . ? C2 C3 C4 110.3(2) . . ? C15 C3 C4 123.63(19) . . ? C3 C4 C18 118.33(18) . . ? C3 C4 C5 98.47(17) . . ? C18 C4 C5 113.79(18) . . ? C3 C4 C8 102.92(17) . . ? C18 C4 C8 117.20(18) . . ? C5 C4 C8 103.50(17) . . ? C6 C5 C21 126.6(2) . . ? C6 C5 C4 111.07(19) . . ? C21 C5 C4 121.9(2) . . ? C5 C6 C7 110.8(2) . . ? C5 C6 C24 126.2(2) . . ? C7 C6 C24 122.9(2) . . ? C6 C7 C8 108.94(19) . . ? C6 C7 C27 118.66(19) . . ? C8 C7 C27 122.4(2) . . ? C6 C7 C1 115.63(18) . . ? C8 C7 C1 56.12(13) . . ? C27 C7 C1 119.78(18) . . ? C7 C8 C1 67.91(15) . . ? C7 C8 C30 125.32(19) . . ? C1 C8 C30 120.43(19) . . ? C7 C8 C4 104.42(17) . . ? C1 C8 C4 104.38(17) . . ? C30 C8 C4 121.55(18) . . ? C10 C9 C1 115.58(19) . . ? C10 C9 H9A 108.4 . . ? C1 C9 H9A 108.4 . . ? C10 C9 H9B 108.4 . . ? C1 C9 H9B 108.4 . . ? H9A C9 H9B 107.4 . . ? C11 C10 C9 111.6(2) . . ? C11 C10 H10A 109.3 . . ? C9 C10 H10A 109.3 . . ? C11 C10 H10B 109.3 . . ? C9 C10 H10B 109.3 . . ? H10A C10 H10B 108.0 . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C2 C12 C13 114.45(19) . . ? C2 C12 H12A 108.6 . . ? C13 C12 H12A 108.6 . . ? C2 C12 H12B 108.6 . . ? C13 C12 H12B 108.6 . . ? H12A C12 H12B 107.6 . . ? C14 C13 C12 112.4(2) . . ? C14 C13 H13A 109.1 . . ? C12 C13 H13A 109.1 . . ? C14 C13 H13B 109.1 . . ? C12 C13 H13B 109.1 . . ? H13A C13 H13B 107.9 . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C3 C15 C16 112.7(2) . . ? C3 C15 H15A 109.1 . . ? C16 C15 H15A 109.1 . . ? C3 C15 H15B 109.1 . . ? C16 C15 H15B 109.1 . . ? H15A C15 H15B 107.8 . . ? C17 C16 C15 112.4(2) . . ? C17 C16 H16A 109.1 . . ? C15 C16 H16A 109.1 . . ? C17 C16 H16B 109.1 . . ? C15 C16 H16B 109.1 . . ? H16A C16 H16B 107.9 . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C19 C18 C4 114.21(18) . . ? C19 C18 H18A 108.7 . . ? C4 C18 H18A 108.7 . . ? C19 C18 H18B 108.7 . . ? C4 C18 H18B 108.7 . . ? H18A C18 H18B 107.6 . . ? C20 C19 C18 113.05(19) . . ? C20 C19 H19A 109.0 . . ? C18 C19 H19A 109.0 . . ? C20 C19 H19B 109.0 . . ? C18 C19 H19B 109.0 . . ? H19A C19 H19B 107.8 . . ? C19 C20 H20A 109.5 . . ? C19 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C19 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C5 C21 C22 116.92(19) . . ? C5 C21 H21A 108.1 . . ? C22 C21 H21A 108.1 . . ? C5 C21 H21B 108.1 . . ? C22 C21 H21B 108.1 . . ? H21A C21 H21B 107.3 . . ? C23 C22 C21 111.80(19) . . ? C23 C22 H22A 109.3 . . ? C21 C22 H22A 109.3 . . ? C23 C22 H22B 109.3 . . ? C21 C22 H22B 109.3 . . ? H22A C22 H22B 107.9 . . ? C22 C23 H23A 109.5 . . ? C22 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C22 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C6 C24 C25 113.01(18) . . ? C6 C24 H24A 109.0 . . ? C25 C24 H24A 109.0 . . ? C6 C24 H24B 109.0 . . ? C25 C24 H24B 109.0 . . ? H24A C24 H24B 107.8 . . ? C26 C25 C24 112.8(2) . . ? C26 C25 H25A 109.0 . . ? C24 C25 H25A 109.0 . . ? C26 C25 H25B 109.0 . . ? C24 C25 H25B 109.0 . . ? H25A C25 H25B 107.8 . . ? C25 C26 H26A 109.5 . . ? C25 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C25 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C7 C27 C28 112.05(19) . . ? C7 C27 H27A 109.2 . . ? C28 C27 H27A 109.2 . . ? C7 C27 H27B 109.2 . . ? C28 C27 H27B 109.2 . . ? H27A C27 H27B 107.9 . . ? C29 C28 C27 113.5(2) . . ? C29 C28 H28A 108.9 . . ? C27 C28 H28A 108.9 . . ? C29 C28 H28B 108.9 . . ? C27 C28 H28B 108.9 . . ? H28A C28 H28B 107.7 . . ? C28 C29 H29A 109.5 . . ? C28 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C28 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C8 C30 C31 113.61(18) . . ? C8 C30 H30A 108.8 . . ? C31 C30 H30A 108.8 . . ? C8 C30 H30B 108.8 . . ? C31 C30 H30B 108.8 . . ? H30A C30 H30B 107.7 . . ? C32 C31 C30 112.62(19) . . ? C32 C31 H31A 109.1 . . ? C30 C31 H31A 109.1 . . ? C32 C31 H31B 109.1 . . ? C30 C31 H31B 109.1 . . ? H31A C31 H31B 107.8 . . ? C31 C32 H32A 109.5 . . ? C31 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C31 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? C34 C33 C40 111.3(2) . . ? C34 C33 C41 123.3(2) . . ? C40 C33 C41 123.5(2) . . ? C33 C34 C35 110.7(2) . . ? C33 C34 C44 123.9(2) . . ? C35 C34 C44 125.4(2) . . ? C34 C35 C36 109.8(2) . . ? C34 C35 C47 122.7(3) . . ? C36 C35 C47 123.9(2) . . ? C34 C35 C37 117.0(2) . . ? C36 C35 C37 49.11(14) . . ? C47 C35 C37 112.7(2) . . ? C37 C36 C35 81.3(2) . . ? C37 C36 C50 123.0(2) . . ? C35 C36 C50 117.6(2) . . ? C37 C36 C40 104.02(18) . . ? C35 C36 C40 104.03(19) . . ? C50 C36 C40 119.56(19) . . ? C38 C37 C36 109.8(2) . . ? C38 C37 C53 123.2(2) . . ? C36 C37 C53 123.4(2) . . ? C38 C37 C35 109.76(18) . . ? C36 C37 C35 49.64(14) . . ? C53 C37 C35 118.86(18) . . ? C39 C38 C37 111.3(2) . . ? C39 C38 C56 125.1(2) . . ? C37 C38 C56 123.5(2) . . ? C38 C39 C40 110.5(2) . . ? C38 C39 C59 124.0(2) . . ? C40 C39 C59 124.0(2) . . ? C33 C40 C39 85.8(2) . . ? C33 C40 C62 121.9(2) . . ? C39 C40 C62 117.0(2) . . ? C33 C40 C36 103.52(18) . . ? C39 C40 C36 104.19(18) . . ? C62 C40 C36 118.78(19) . . ? C33 C41 C42 112.1(2) . . ? C33 C41 H41A 109.2 . . ? C42 C41 H41A 109.2 . . ? C33 C41 H41B 109.2 . . ? C42 C41 H41B 109.2 . . ? H41A C41 H41B 107.9 . . ? C43 C42 C41 112.5(2) . . ? C43 C42 H42A 109.1 . . ? C41 C42 H42A 109.1 . . ? C43 C42 H42B 109.1 . . ? C41 C42 H42B 109.1 . . ? H42A C42 H42B 107.8 . . ? C42 C43 H43A 109.5 . . ? C42 C43 H43B 109.5 . . ? H43A C43 H43B 109.5 . . ? C42 C43 H43C 109.5 . . ? H43A C43 H43C 109.5 . . ? H43B C43 H43C 109.5 . . ? C34 C44 C45 113.63(19) . . ? C34 C44 H44A 108.8 . . ? C45 C44 H44A 108.8 . . ? C34 C44 H44B 108.8 . . ? C45 C44 H44B 108.8 . . ? H44A C44 H44B 107.7 . . ? C46 C45 C44 113.5(2) . . ? C46 C45 H45A 108.9 . . ? C44 C45 H45A 108.9 . . ? C46 C45 H45B 108.9 . . ? C44 C45 H45B 108.9 . . ? H45A C45 H45B 107.7 . . ? C45 C46 H46A 109.5 . . ? C45 C46 H46B 109.5 . . ? H46A C46 H46B 109.5 . . ? C45 C46 H46C 109.5 . . ? H46A C46 H46C 109.5 . . ? H46B C46 H46C 109.5 . . ? C48 C47 C35 115.7(2) . . ? C48 C47 H47A 108.4 . . ? C35 C47 H47A 108.4 . . ? C48 C47 H47B 108.4 . . ? C35 C47 H47B 108.4 . . ? H47A C47 H47B 107.4 . . ? C49 C48 C47 112.3(2) . . ? C49 C48 H48A 109.1 . . ? C47 C48 H48A 109.1 . . ? C49 C48 H48B 109.1 . . ? C47 C48 H48B 109.1 . . ? H48A C48 H48B 107.9 . . ? C48 C49 H49A 109.5 . . ? C48 C49 H49B 109.5 . . ? H49A C49 H49B 109.5 . . ? C48 C49 H49C 109.5 . . ? H49A C49 H49C 109.5 . . ? H49B C49 H49C 109.5 . . ? C36 C50 C51 113.61(18) . . ? C36 C50 H50A 108.8 . . ? C51 C50 H50A 108.8 . . ? C36 C50 H50B 108.8 . . ? C51 C50 H50B 108.8 . . ? H50A C50 H50B 107.7 . . ? C52 C51 C50 112.21(19) . . ? C52 C51 H51A 109.2 . . ? C50 C51 H51A 109.2 . . ? C52 C51 H51B 109.2 . . ? C50 C51 H51B 109.2 . . ? H51A C51 H51B 107.9 . . ? C51 C52 H52A 109.5 . . ? C51 C52 H52B 109.5 . . ? H52A C52 H52B 109.5 . . ? C51 C52 H52C 109.5 . . ? H52A C52 H52C 109.5 . . ? H52B C52 H52C 109.5 . . ? C37 C53 C54 111.6(2) . . ? C37 C53 H53A 109.3 . . ? C54 C53 H53A 109.3 . . ? C37 C53 H53B 109.3 . . ? C54 C53 H53B 109.3 . . ? H53A C53 H53B 108.0 . . ? C55 C54 C53 113.8(2) . . ? C55 C54 H54A 108.8 . . ? C53 C54 H54A 108.8 . . ? C55 C54 H54B 108.8 . . ? C53 C54 H54B 108.8 . . ? H54A C54 H54B 107.7 . . ? C54 C55 H55A 109.5 . . ? C54 C55 H55B 109.5 . . ? H55A C55 H55B 109.5 . . ? C54 C55 H55C 109.5 . . ? H55A C55 H55C 109.5 . . ? H55B C55 H55C 109.5 . . ? C38 C56 C57 114.73(19) . . ? C38 C56 H56A 108.6 . . ? C57 C56 H56A 108.6 . . ? C38 C56 H56B 108.6 . . ? C57 C56 H56B 108.6 . . ? H56A C56 H56B 107.6 . . ? C56 C57 C58 113.6(2) . . ? C56 C57 H57A 108.9 . . ? C58 C57 H57A 108.9 . . ? C56 C57 H57B 108.9 . . ? C58 C57 H57B 108.9 . . ? H57A C57 H57B 107.7 . . ? C57 C58 H58A 109.5 . . ? C57 C58 H58B 109.5 . . ? H58A C58 H58B 109.5 . . ? C57 C58 H58C 109.5 . . ? H58A C58 H58C 109.5 . . ? H58B C58 H58C 109.5 . . ? C39 C59 C60 116.1(2) . . ? C39 C59 H59A 108.3 . . ? C60 C59 H59A 108.3 . . ? C39 C59 H59B 108.3 . . ? C60 C59 H59B 108.3 . . ? H59A C59 H59B 107.4 . . ? C61 C60 C59 112.56(19) . . ? C61 C60 H60A 109.1 . . ? C59 C60 H60A 109.1 . . ? C61 C60 H60B 109.1 . . ? C59 C60 H60B 109.1 . . ? H60A C60 H60B 107.8 . . ? C60 C61 H61A 109.5 . . ? C60 C61 H61B 109.5 . . ? H61A C61 H61B 109.5 . . ? C60 C61 H61C 109.5 . . ? H61A C61 H61C 109.5 . . ? H61B C61 H61C 109.5 . . ? C40 C62 C63 114.03(18) . . ? C40 C62 H62A 108.7 . . ? C63 C62 H62A 108.7 . . ? C40 C62 H62B 108.7 . . ? C63 C62 H62B 108.7 . . ? H62A C62 H62B 107.6 . . ? C64 C63 C62 113.56(19) . . ? C64 C63 H63A 108.9 . . ? C62 C63 H63A 108.9 . . ? C64 C63 H63B 108.9 . . ? C62 C63 H63B 108.9 . . ? H63A C63 H63B 107.7 . . ? C63 C64 H64A 109.5 . . ? C63 C64 H64B 109.5 . . ? H64A C64 H64B 109.5 . . ? C63 C64 H64C 109.5 . . ? H64A C64 H64C 109.5 . . ? H64B C64 H64C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C8 C1 C2 C3 5.9(3) . . . . ? C9 C1 C2 C3 149.3(2) . . . . ? C7 C1 C2 C3 -54.0(3) . . . . ? C8 C1 C2 C12 -174.4(2) . . . . ? C9 C1 C2 C12 -31.0(3) . . . . ? C7 C1 C2 C12 125.7(2) . . . . ? C1 C2 C3 C15 -174.3(2) . . . . ? C12 C2 C3 C15 6.0(4) . . . . ? C1 C2 C3 C4 8.4(3) . . . . ? C12 C2 C3 C4 -171.3(2) . . . . ? C2 C3 C4 C18 -149.5(2) . . . . ? C15 C3 C4 C18 33.0(3) . . . . ? C2 C3 C4 C5 87.5(2) . . . . ? C15 C3 C4 C5 -89.9(2) . . . . ? C2 C3 C4 C8 -18.5(2) . . . . ? C15 C3 C4 C8 164.0(2) . . . . ? C3 C4 C5 C6 -95.5(2) . . . . ? C18 C4 C5 C6 138.3(2) . . . . ? C8 C4 C5 C6 10.0(2) . . . . ? C3 C4 C5 C21 77.4(2) . . . . ? C18 C4 C5 C21 -48.8(3) . . . . ? C8 C4 C5 C21 -177.1(2) . . . . ? C21 C5 C6 C7 -177.3(2) . . . . ? C4 C5 C6 C7 -4.8(3) . . . . ? C21 C5 C6 C24 -0.5(4) . . . . ? C4 C5 C6 C24 172.0(2) . . . . ? C5 C6 C7 C8 -2.7(3) . . . . ? C24 C6 C7 C8 -179.63(19) . . . . ? C5 C6 C7 C27 -149.1(2) . . . . ? C24 C6 C7 C27 34.0(3) . . . . ? C5 C6 C7 C1 58.0(3) . . . . ? C24 C6 C7 C1 -118.9(2) . . . . ? C2 C1 C7 C6 -6.7(3) . . . . ? C8 C1 C7 C6 -96.4(2) . . . . ? C9 C1 C7 C6 150.3(2) . . . . ? C2 C1 C7 C8 89.7(2) . . . . ? C9 C1 C7 C8 -113.3(2) . . . . ? C2 C1 C7 C27 -159.3(2) . . . . ? C8 C1 C7 C27 111.1(2) . . . . ? C9 C1 C7 C27 -2.2(3) . . . . ? C6 C7 C8 C1 108.7(2) . . . . ? C27 C7 C8 C1 -106.4(2) . . . . ? C6 C7 C8 C30 -138.8(2) . . . . ? C27 C7 C8 C30 6.1(3) . . . . ? C1 C7 C8 C30 112.5(2) . . . . ? C6 C7 C8 C4 8.8(2) . . . . ? C27 C7 C8 C4 153.67(19) . . . . ? C1 C7 C8 C4 -99.93(18) . . . . ? C2 C1 C8 C7 -116.9(2) . . . . ? C9 C1 C8 C7 101.8(2) . . . . ? C2 C1 C8 C30 124.0(2) . . . . ? C9 C1 C8 C30 -17.2(3) . . . . ? C7 C1 C8 C30 -119.0(2) . . . . ? C2 C1 C8 C4 -17.0(2) . . . . ? C9 C1 C8 C4 -158.2(2) . . . . ? C7 C1 C8 C4 99.98(18) . . . . ? C3 C4 C8 C7 91.32(19) . . . . ? C18 C4 C8 C7 -136.98(18) . . . . ? C5 C4 C8 C7 -10.8(2) . . . . ? C3 C4 C8 C1 20.9(2) . . . . ? C18 C4 C8 C1 152.60(19) . . . . ? C5 C4 C8 C1 -81.3(2) . . . . ? C3 C4 C8 C30 -119.6(2) . . . . ? C18 C4 C8 C30 12.2(3) . . . . ? C5 C4 C8 C30 138.29(19) . . . . ? C2 C1 C9 C10 87.3(3) . . . . ? C8 C1 C9 C10 -135.6(2) . . . . ? C7 C1 C9 C10 -70.6(3) . . . . ? C1 C9 C10 C11 180.0(2) . . . . ? C3 C2 C12 C13 90.7(3) . . . . ? C1 C2 C12 C13 -89.0(3) . . . . ? C2 C12 C13 C14 176.9(2) . . . . ? C2 C3 C15 C16 90.5(3) . . . . ? C4 C3 C15 C16 -92.5(3) . . . . ? C3 C15 C16 C17 174.45(19) . . . . ? C3 C4 C18 C19 -161.29(19) . . . . ? C5 C4 C18 C19 -46.4(3) . . . . ? C8 C4 C18 C19 74.5(2) . . . . ? C4 C18 C19 C20 -171.68(19) . . . . ? C6 C5 C21 C22 65.1(3) . . . . ? C4 C5 C21 C22 -106.6(2) . . . . ? C5 C21 C22 C23 170.9(2) . . . . ? C5 C6 C24 C25 -104.6(3) . . . . ? C7 C6 C24 C25 71.8(3) . . . . ? C6 C24 C25 C26 176.9(2) . . . . ? C6 C7 C27 C28 65.9(3) . . . . ? C8 C7 C27 C28 -75.8(3) . . . . ? C1 C7 C27 C28 -142.4(2) . . . . ? C7 C27 C28 C29 179.6(2) . . . . ? C7 C8 C30 C31 -143.1(2) . . . . ? C1 C8 C30 C31 -59.9(3) . . . . ? C4 C8 C30 C31 74.5(3) . . . . ? C8 C30 C31 C32 -176.8(2) . . . . ? C40 C33 C34 C35 -3.1(3) . . . . ? C41 C33 C34 C35 161.4(3) . . . . ? C40 C33 C34 C44 173.9(2) . . . . ? C41 C33 C34 C44 -21.6(4) . . . . ? C33 C34 C35 C36 -2.5(3) . . . . ? C44 C34 C35 C36 -179.4(2) . . . . ? C33 C34 C35 C47 -162.0(3) . . . . ? C44 C34 C35 C47 21.1(4) . . . . ? C33 C34 C35 C37 50.8(3) . . . . ? C44 C34 C35 C37 -126.1(2) . . . . ? C34 C35 C36 C37 109.0(3) . . . . ? C47 C35 C36 C37 -91.8(3) . . . . ? C34 C35 C36 C50 -128.1(2) . . . . ? C47 C35 C36 C50 31.0(4) . . . . ? C37 C35 C36 C50 122.8(2) . . . . ? C34 C35 C36 C40 6.7(3) . . . . ? C47 C35 C36 C40 165.8(3) . . . . ? C37 C35 C36 C40 -102.37(19) . . . . ? C35 C36 C37 C38 -99.5(2) . . . . ? C50 C36 C37 C38 143.1(2) . . . . ? C40 C36 C37 C38 2.9(3) . . . . ? C35 C36 C37 C53 101.5(3) . . . . ? C50 C36 C37 C53 -15.9(4) . . . . ? C40 C36 C37 C53 -156.2(2) . . . . ? C50 C36 C37 C35 -117.3(3) . . . . ? C40 C36 C37 C35 102.4(2) . . . . ? C34 C35 C37 C38 6.1(3) . . . . ? C36 C35 C37 C38 99.7(2) . . . . ? C47 C35 C37 C38 -144.3(2) . . . . ? C34 C35 C37 C36 -93.6(3) . . . . ? C47 C35 C37 C36 116.0(2) . . . . ? C34 C35 C37 C53 155.6(2) . . . . ? C36 C35 C37 C53 -110.9(2) . . . . ? C47 C35 C37 C53 5.2(3) . . . . ? C36 C37 C38 C39 -1.3(3) . . . . ? C53 C37 C38 C39 157.8(3) . . . . ? C35 C37 C38 C39 -54.3(3) . . . . ? C36 C37 C38 C56 175.6(2) . . . . ? C53 C37 C38 C56 -25.3(4) . . . . ? C35 C37 C38 C56 122.6(2) . . . . ? C37 C38 C39 C40 -0.9(3) . . . . ? C56 C38 C39 C40 -177.8(2) . . . . ? C37 C38 C39 C59 -167.7(2) . . . . ? C56 C38 C39 C59 15.5(4) . . . . ? C34 C33 C40 C39 -96.5(2) . . . . ? C41 C33 C40 C39 99.0(2) . . . . ? C34 C33 C40 C62 144.1(2) . . . . ? C41 C33 C40 C62 -20.3(3) . . . . ? C34 C33 C40 C36 7.0(3) . . . . ? C41 C33 C40 C36 -157.4(2) . . . . ? C38 C39 C40 C33 105.6(3) . . . . ? C59 C39 C40 C33 -87.7(3) . . . . ? C38 C39 C40 C62 -130.6(2) . . . . ? C59 C39 C40 C62 36.1(4) . . . . ? C38 C39 C40 C36 2.7(3) . . . . ? C59 C39 C40 C36 169.4(2) . . . . ? C37 C36 C40 C33 -92.2(2) . . . . ? C35 C36 C40 C33 -7.9(2) . . . . ? C50 C36 C40 C33 125.8(2) . . . . ? C37 C36 C40 C39 -3.2(3) . . . . ? C35 C36 C40 C39 81.1(3) . . . . ? C50 C36 C40 C39 -145.2(2) . . . . ? C37 C36 C40 C62 129.1(2) . . . . ? C35 C36 C40 C62 -146.6(2) . . . . ? C50 C36 C40 C62 -12.9(3) . . . . ? C34 C33 C41 C42 -78.2(3) . . . . ? C40 C33 C41 C42 84.4(3) . . . . ? C33 C41 C42 C43 179.5(2) . . . . ? C33 C34 C44 C45 -80.0(3) . . . . ? C35 C34 C44 C45 96.5(3) . . . . ? C34 C44 C45 C46 -179.8(2) . . . . ? C34 C35 C47 C48 -81.3(4) . . . . ? C36 C35 C47 C48 122.1(3) . . . . ? C37 C35 C47 C48 67.2(3) . . . . ? C35 C47 C48 C49 -178.1(2) . . . . ? C37 C36 C50 C51 151.4(2) . . . . ? C35 C36 C50 C51 53.6(3) . . . . ? C40 C36 C50 C51 -74.1(3) . . . . ? C36 C50 C51 C52 172.1(2) . . . . ? C38 C37 C53 C54 -74.6(3) . . . . ? C36 C37 C53 C54 81.7(3) . . . . ? C35 C37 C53 C54 140.2(2) . . . . ? C37 C53 C54 C55 -175.2(2) . . . . ? C39 C38 C56 C57 98.9(3) . . . . ? C37 C38 C56 C57 -77.6(3) . . . . ? C38 C56 C57 C58 -176.0(2) . . . . ? C38 C39 C59 C60 -77.3(4) . . . . ? C40 C39 C59 C60 117.7(3) . . . . ? C39 C59 C60 C61 -172.1(2) . . . . ? C33 C40 C62 C63 153.9(2) . . . . ? C39 C40 C62 C63 51.3(3) . . . . ? C36 C40 C62 C63 -75.1(3) . . . . ? C40 C62 C63 C64 173.4(2) . . . . ? _diffrn_measured_fraction_theta_max 0.967 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.967 _refine_diff_density_max 0.277 _refine_diff_density_min -0.213 _refine_diff_density_rms 0.039 _database_code_depnum_ccdc_archive 'CCDC 966204' ####################################################################### # # 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_a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C34 H24 O2' _chemical_formula_sum 'C34 H24 O2' _chemical_formula_weight 464.53 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 monoclinic _symmetry_space_group_name_H-M P2(1)/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 11.409(2) _cell_length_b 8.8005(18) _cell_length_c 24.458(5) _cell_angle_alpha 90.00 _cell_angle_beta 102.84(3) _cell_angle_gamma 90.00 _cell_volume 2394.3(8) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 6851 _cell_measurement_theta_min 1.7080 _cell_measurement_theta_max 27.4797 _exptl_crystal_description block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.289 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 976 _exptl_absorpt_coefficient_mu 0.079 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6771 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'CrystalClear (Rigaku Inc., 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'Saturn724+ CCD' _diffrn_measurement_method '\w scans at fixed \c = 45\%' _diffrn_detector_area_resol_mean 28.5714 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15719 _diffrn_reflns_av_R_equivalents 0.0443 _diffrn_reflns_av_sigmaI/netI 0.0488 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 2.95 _diffrn_reflns_theta_max 27.47 _reflns_number_total 5384 _reflns_number_gt 4713 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2008)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2008)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2008)' _computing_structure_solution 'SHELX-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELX-97 (Sheldrick, 2008)' _computing_molecular_graphics ; Mercury: visualization and analysis of crystal structures, C. F. Macrae, P. R. Edgington, P. McCabe, E. Pidcock, G. P. Shields, R. Taylor, M. Towler and J. van de Streek, J. Appl. Cryst., 39, 453-457, 2006. ; _computing_publication_material 'SHELX-97 (Sheldrick, 2008)' _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^)+(0.0279P)^2^+1.1828P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5384 _refine_ls_number_parameters 325 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0870 _refine_ls_R_factor_gt 0.0744 _refine_ls_wR_factor_ref 0.1370 _refine_ls_wR_factor_gt 0.1312 _refine_ls_goodness_of_fit_ref 1.217 _refine_ls_restrained_S_all 1.217 _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 O1 O 0.60671(14) 0.65197(16) 0.09054(6) 0.0386(4) Uani 1 1 d . . . O2 O 0.41420(15) 0.07522(19) 0.06175(7) 0.0497(4) Uani 1 1 d . . . C1 C 0.5148(2) 0.1261(2) 0.06367(9) 0.0351(5) Uani 1 1 d . . . C2 C 0.6275(2) 0.0421(2) 0.07446(9) 0.0357(5) Uani 1 1 d . . . H2 H 0.6340 -0.0642 0.0811 0.043 Uiso 1 1 calc R . . C3 C 0.72127(19) 0.1342(2) 0.07382(8) 0.0298(4) Uani 1 1 d . . . C4 C 0.8463(2) 0.0846(2) 0.07835(8) 0.0330(5) Uani 1 1 d . . . C5 C 0.8701(2) -0.0620(3) 0.06151(10) 0.0431(6) Uani 1 1 d . . . H5 H 0.8056 -0.1306 0.0486 0.052 Uiso 1 1 calc R . . C6 C 0.9869(2) -0.1078(3) 0.06346(11) 0.0518(7) Uani 1 1 d . . . H6 H 1.0020 -0.2076 0.0519 0.062 Uiso 1 1 calc R . . C7 C 1.0818(2) -0.0096(3) 0.08213(10) 0.0493(6) Uani 1 1 d . . . H7 H 1.1618 -0.0413 0.0831 0.059 Uiso 1 1 calc R . . C8 C 1.0597(2) 0.1345(3) 0.09926(10) 0.0443(6) Uani 1 1 d . . . H8 H 1.1248 0.2019 0.1127 0.053 Uiso 1 1 calc R . . C9 C 0.9432(2) 0.1813(3) 0.09700(10) 0.0392(5) Uani 1 1 d . . . H9 H 0.9290 0.2816 0.1084 0.047 Uiso 1 1 calc R . . C10 C 0.68299(18) 0.3002(2) 0.06316(8) 0.0282(4) Uani 1 1 d . . . C11 C 0.72470(18) 0.3643(2) 0.01243(8) 0.0289(4) Uani 1 1 d . . . C12 C 0.69994(19) 0.2835(2) -0.03782(9) 0.0337(5) Uani 1 1 d . . . H12 H 0.6555 0.1915 -0.0404 0.040 Uiso 1 1 calc R . . C13 C 0.7397(2) 0.3363(3) -0.08417(9) 0.0379(5) Uani 1 1 d . . . H13 H 0.7214 0.2807 -0.1183 0.045 Uiso 1 1 calc R . . C14 C 0.8055(2) 0.4691(3) -0.08086(9) 0.0413(6) Uani 1 1 d . . . H14 H 0.8345 0.5036 -0.1122 0.050 Uiso 1 1 calc R . . C15 C 0.8287(2) 0.5505(3) -0.03189(10) 0.0477(6) Uani 1 1 d . . . H15 H 0.8726 0.6429 -0.0297 0.057 Uiso 1 1 calc R . . C16 C 0.7887(2) 0.4995(3) 0.01457(9) 0.0401(5) Uani 1 1 d . . . H16 H 0.8052 0.5576 0.0481 0.048 Uiso 1 1 calc R . . C17 C 0.71694(18) 0.4079(2) 0.11575(8) 0.0279(4) Uani 1 1 d . . . H17 H 0.7986 0.4553 0.1225 0.033 Uiso 1 1 calc R . . C18 C 0.61009(19) 0.5181(2) 0.09999(8) 0.0308(5) Uani 1 1 d . . . C19 C 0.51124(19) 0.3998(2) 0.09999(8) 0.0313(5) Uani 1 1 d . . . H19 H 0.4269 0.4390 0.0928 0.038 Uiso 1 1 calc R . . C20 C 0.54205(19) 0.2920(2) 0.05474(8) 0.0313(5) Uani 1 1 d . . . H20 H 0.5013 0.3261 0.0162 0.038 Uiso 1 1 calc R . . C21 C 0.68329(18) 0.3360(2) 0.16644(8) 0.0284(4) Uani 1 1 d . . . C22 C 0.77538(18) 0.2780(2) 0.21427(8) 0.0300(4) Uani 1 1 d . . . C23 C 0.8720(2) 0.3692(3) 0.23982(9) 0.0371(5) Uani 1 1 d . . . H23 H 0.8791 0.4688 0.2259 0.045 Uiso 1 1 calc R . . C24 C 0.9576(2) 0.3168(3) 0.28511(10) 0.0453(6) Uani 1 1 d . . . H24 H 1.0217 0.3812 0.3028 0.054 Uiso 1 1 calc R . . C25 C 0.9496(2) 0.1712(3) 0.30448(10) 0.0485(6) Uani 1 1 d . . . H25 H 1.0081 0.1350 0.3357 0.058 Uiso 1 1 calc R . . C26 C 0.8564(2) 0.0778(3) 0.27852(9) 0.0444(6) Uani 1 1 d . . . H26 H 0.8522 -0.0236 0.2913 0.053 Uiso 1 1 calc R . . C27 C 0.7695(2) 0.1308(3) 0.23427(9) 0.0367(5) Uani 1 1 d . . . H27 H 0.7050 0.0663 0.2172 0.044 Uiso 1 1 calc R . . C28 C 0.56187(19) 0.3352(2) 0.15814(8) 0.0305(4) Uani 1 1 d . . . C29 C 0.48703(19) 0.2956(2) 0.19818(9) 0.0319(5) Uani 1 1 d . . . C30 C 0.5260(2) 0.3289(3) 0.25508(9) 0.0393(5) Uani 1 1 d . . . H30 H 0.6025 0.3748 0.2682 0.047 Uiso 1 1 calc R . . C31 C 0.4551(2) 0.2963(3) 0.29271(10) 0.0435(6) Uani 1 1 d . . . H31 H 0.4827 0.3202 0.3313 0.052 Uiso 1 1 calc R . . C32 C 0.3437(2) 0.2286(3) 0.27409(10) 0.0452(6) Uani 1 1 d . . . H32 H 0.2951 0.2049 0.2998 0.054 Uiso 1 1 calc R . . C33 C 0.3043(2) 0.1961(3) 0.21805(10) 0.0461(6) Uani 1 1 d . . . H33 H 0.2278 0.1499 0.2052 0.055 Uiso 1 1 calc R . . C34 C 0.3742(2) 0.2294(3) 0.18010(10) 0.0397(5) Uani 1 1 d . . . H34 H 0.3451 0.2070 0.1415 0.048 Uiso 1 1 calc R . . 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 0.0527(10) 0.0261(8) 0.0370(8) 0.0027(6) 0.0098(7) 0.0016(7) O2 0.0419(10) 0.0426(9) 0.0652(11) -0.0107(9) 0.0136(8) -0.0152(8) C1 0.0390(13) 0.0334(11) 0.0324(11) -0.0075(9) 0.0070(9) -0.0097(10) C2 0.0448(14) 0.0247(10) 0.0378(11) -0.0008(9) 0.0096(10) -0.0043(9) C3 0.0388(12) 0.0252(10) 0.0250(10) -0.0005(8) 0.0060(9) 0.0005(9) C4 0.0406(13) 0.0286(10) 0.0286(10) 0.0035(8) 0.0054(9) 0.0037(9) C5 0.0476(15) 0.0360(12) 0.0420(13) -0.0029(10) 0.0021(11) 0.0057(11) C6 0.0559(17) 0.0472(15) 0.0490(14) -0.0064(12) 0.0045(12) 0.0201(13) C7 0.0438(15) 0.0583(16) 0.0447(14) 0.0079(12) 0.0074(11) 0.0149(13) C8 0.0371(14) 0.0473(14) 0.0468(13) 0.0101(11) 0.0056(11) 0.0034(11) C9 0.0395(13) 0.0311(11) 0.0464(13) 0.0009(10) 0.0080(10) 0.0033(10) C10 0.0304(11) 0.0264(10) 0.0265(10) 0.0001(8) 0.0037(8) -0.0012(8) C11 0.0308(11) 0.0256(10) 0.0297(10) 0.0018(8) 0.0053(8) 0.0025(8) C12 0.0372(12) 0.0284(10) 0.0336(11) -0.0008(9) 0.0042(9) 0.0023(9) C13 0.0485(14) 0.0386(12) 0.0270(10) -0.0034(9) 0.0093(10) 0.0098(10) C14 0.0465(14) 0.0454(13) 0.0356(12) 0.0063(10) 0.0169(11) 0.0038(11) C15 0.0610(17) 0.0441(14) 0.0409(13) 0.0015(11) 0.0179(12) -0.0155(12) C16 0.0542(15) 0.0352(12) 0.0316(11) -0.0028(9) 0.0110(10) -0.0115(11) C17 0.0318(11) 0.0241(10) 0.0268(10) 0.0009(8) 0.0044(8) -0.0033(8) C18 0.0409(12) 0.0302(11) 0.0204(9) -0.0006(8) 0.0047(8) 0.0008(9) C19 0.0320(12) 0.0288(10) 0.0330(10) 0.0022(9) 0.0069(9) 0.0005(9) C20 0.0335(12) 0.0311(10) 0.0281(10) 0.0008(8) 0.0041(9) -0.0002(9) C21 0.0338(12) 0.0226(9) 0.0287(10) 0.0013(8) 0.0065(9) -0.0009(8) C22 0.0325(12) 0.0313(10) 0.0269(10) -0.0002(8) 0.0083(9) 0.0021(9) C23 0.0373(13) 0.0382(12) 0.0341(11) 0.0012(9) 0.0041(10) -0.0030(10) C24 0.0364(13) 0.0596(16) 0.0370(12) -0.0022(11) 0.0014(10) -0.0018(11) C25 0.0477(15) 0.0621(17) 0.0311(12) 0.0030(12) -0.0009(11) 0.0168(13) C26 0.0603(16) 0.0391(13) 0.0333(12) 0.0083(10) 0.0093(11) 0.0094(12) C27 0.0448(13) 0.0344(11) 0.0305(10) 0.0030(9) 0.0074(10) 0.0003(10) C28 0.0349(12) 0.0265(10) 0.0297(10) 0.0000(8) 0.0065(9) 0.0000(9) C29 0.0336(12) 0.0293(10) 0.0329(11) 0.0044(9) 0.0076(9) 0.0034(9) C30 0.0388(13) 0.0424(13) 0.0373(12) -0.0021(10) 0.0100(10) -0.0033(10) C31 0.0457(15) 0.0518(15) 0.0335(11) 0.0048(11) 0.0099(10) 0.0059(12) C32 0.0402(14) 0.0559(15) 0.0423(13) 0.0157(12) 0.0154(11) 0.0051(12) C33 0.0360(13) 0.0560(15) 0.0456(13) 0.0127(12) 0.0079(11) -0.0056(11) C34 0.0369(13) 0.0450(13) 0.0361(11) 0.0083(10) 0.0061(10) -0.0013(10) _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 C18 1.200(2) . ? O2 C1 1.223(3) . ? C1 C2 1.456(3) . ? C1 C20 1.519(3) . ? C2 C3 1.345(3) . ? C2 H2 0.9500 . ? C3 C4 1.472(3) . ? C3 C10 1.530(3) . ? C4 C9 1.390(3) . ? C4 C5 1.400(3) . ? C5 C6 1.382(3) . ? C5 H5 0.9500 . ? C6 C7 1.381(4) . ? C6 H6 0.9500 . ? C7 C8 1.376(4) . ? C7 H7 0.9500 . ? C8 C9 1.381(3) . ? C8 H8 0.9500 . ? C9 H9 0.9500 . ? C10 C11 1.532(3) . ? C10 C17 1.575(3) . ? C10 C20 1.577(3) . ? C11 C16 1.390(3) . ? C11 C12 1.393(3) . ? C12 C13 1.391(3) . ? C12 H12 0.9500 . ? C13 C14 1.382(3) . ? C13 H13 0.9500 . ? C14 C15 1.370(3) . ? C14 H14 0.9500 . ? C15 C16 1.390(3) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C17 C21 1.515(3) . ? C17 C18 1.538(3) . ? C17 H17 1.0000 . ? C18 C19 1.535(3) . ? C19 C28 1.521(3) . ? C19 C20 1.556(3) . ? C19 H19 1.0000 . ? C20 H20 1.0000 . ? C21 C28 1.355(3) . ? C21 C22 1.479(3) . ? C22 C27 1.391(3) . ? C22 C23 1.394(3) . ? C23 C24 1.383(3) . ? C23 H23 0.9500 . ? C24 C25 1.376(4) . ? C24 H24 0.9500 . ? C25 C26 1.382(4) . ? C25 H25 0.9500 . ? C26 C27 1.376(3) . ? C26 H26 0.9500 . ? C27 H27 0.9500 . ? C28 C29 1.477(3) . ? C29 C34 1.392(3) . ? C29 C30 1.395(3) . ? C30 C31 1.384(3) . ? C30 H30 0.9500 . ? C31 C32 1.385(3) . ? C31 H31 0.9500 . ? C32 C33 1.375(3) . ? C32 H32 0.9500 . ? C33 C34 1.383(3) . ? C33 H33 0.9500 . ? C34 H34 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 O2 C1 C2 127.2(2) . . ? O2 C1 C20 124.5(2) . . ? C2 C1 C20 108.25(18) . . ? C3 C2 C1 111.41(19) . . ? C3 C2 H2 124.3 . . ? C1 C2 H2 124.3 . . ? C2 C3 C4 125.47(19) . . ? C2 C3 C10 112.30(19) . . ? C4 C3 C10 122.08(18) . . ? C9 C4 C5 118.0(2) . . ? C9 C4 C3 121.99(19) . . ? C5 C4 C3 120.0(2) . . ? C6 C5 C4 120.5(2) . . ? C6 C5 H5 119.7 . . ? C4 C5 H5 119.7 . . ? C7 C6 C5 120.5(2) . . ? C7 C6 H6 119.7 . . ? C5 C6 H6 119.7 . . ? C8 C7 C6 119.6(2) . . ? C8 C7 H7 120.2 . . ? C6 C7 H7 120.2 . . ? C7 C8 C9 120.1(2) . . ? C7 C8 H8 119.9 . . ? C9 C8 H8 119.9 . . ? C8 C9 C4 121.3(2) . . ? C8 C9 H9 119.4 . . ? C4 C9 H9 119.4 . . ? C3 C10 C11 111.18(16) . . ? C3 C10 C17 115.23(16) . . ? C11 C10 C17 112.05(16) . . ? C3 C10 C20 102.88(16) . . ? C11 C10 C20 113.73(16) . . ? C17 C10 C20 101.11(16) . . ? C16 C11 C12 118.14(19) . . ? C16 C11 C10 122.64(18) . . ? C12 C11 C10 119.20(18) . . ? C13 C12 C11 120.6(2) . . ? C13 C12 H12 119.7 . . ? C11 C12 H12 119.7 . . ? C14 C13 C12 120.4(2) . . ? C14 C13 H13 119.8 . . ? C12 C13 H13 119.8 . . ? C15 C14 C13 119.4(2) . . ? C15 C14 H14 120.3 . . ? C13 C14 H14 120.3 . . ? C14 C15 C16 120.7(2) . . ? C14 C15 H15 119.6 . . ? C16 C15 H15 119.6 . . ? C15 C16 C11 120.7(2) . . ? C15 C16 H16 119.6 . . ? C11 C16 H16 119.6 . . ? C21 C17 C18 97.91(16) . . ? C21 C17 C10 110.83(16) . . ? C18 C17 C10 97.90(15) . . ? C21 C17 H17 115.8 . . ? C18 C17 H17 115.8 . . ? C10 C17 H17 115.8 . . ? O1 C18 C19 132.4(2) . . ? O1 C18 C17 131.1(2) . . ? C19 C18 C17 96.54(16) . . ? C28 C19 C18 97.30(16) . . ? C28 C19 C20 109.77(16) . . ? C18 C19 C20 97.55(16) . . ? C28 C19 H19 116.4 . . ? C18 C19 H19 116.4 . . ? C20 C19 H19 116.4 . . ? C1 C20 C19 113.46(17) . . ? C1 C20 C10 105.10(17) . . ? C19 C20 C10 105.33(16) . . ? C1 C20 H20 110.9 . . ? C19 C20 H20 110.9 . . ? C10 C20 H20 110.9 . . ? C28 C21 C22 129.79(18) . . ? C28 C21 C17 108.42(18) . . ? C22 C21 C17 121.78(17) . . ? C27 C22 C23 118.2(2) . . ? C27 C22 C21 121.22(19) . . ? C23 C22 C21 120.53(19) . . ? C24 C23 C22 121.0(2) . . ? C24 C23 H23 119.5 . . ? C22 C23 H23 119.5 . . ? C25 C24 C23 119.8(2) . . ? C25 C24 H24 120.1 . . ? C23 C24 H24 120.1 . . ? C24 C25 C26 119.9(2) . . ? C24 C25 H25 120.0 . . ? C26 C25 H25 120.0 . . ? C27 C26 C25 120.4(2) . . ? C27 C26 H26 119.8 . . ? C25 C26 H26 119.8 . . ? C26 C27 C22 120.7(2) . . ? C26 C27 H27 119.7 . . ? C22 C27 H27 119.7 . . ? C21 C28 C29 128.64(19) . . ? C21 C28 C19 107.54(18) . . ? C29 C28 C19 123.56(18) . . ? C34 C29 C30 118.2(2) . . ? C34 C29 C28 121.20(19) . . ? C30 C29 C28 120.56(19) . . ? C31 C30 C29 121.0(2) . . ? C31 C30 H30 119.5 . . ? C29 C30 H30 119.5 . . ? C30 C31 C32 120.0(2) . . ? C30 C31 H31 120.0 . . ? C32 C31 H31 120.0 . . ? C33 C32 C31 119.4(2) . . ? C33 C32 H32 120.3 . . ? C31 C32 H32 120.3 . . ? C32 C33 C34 121.0(2) . . ? C32 C33 H33 119.5 . . ? C34 C33 H33 119.5 . . ? C33 C34 C29 120.4(2) . . ? C33 C34 H34 119.8 . . ? C29 C34 H34 119.8 . . ? 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 O2 C1 C2 C3 -179.7(2) . . . . ? C20 C1 C2 C3 0.5(2) . . . . ? C1 C2 C3 C4 -174.44(19) . . . . ? C1 C2 C3 C10 1.1(2) . . . . ? C2 C3 C4 C9 -156.8(2) . . . . ? C10 C3 C4 C9 28.1(3) . . . . ? C2 C3 C4 C5 25.8(3) . . . . ? C10 C3 C4 C5 -149.3(2) . . . . ? C9 C4 C5 C6 -0.1(3) . . . . ? C3 C4 C5 C6 177.4(2) . . . . ? C4 C5 C6 C7 0.1(4) . . . . ? C5 C6 C7 C8 0.5(4) . . . . ? C6 C7 C8 C9 -1.0(4) . . . . ? C7 C8 C9 C4 0.9(4) . . . . ? C5 C4 C9 C8 -0.4(3) . . . . ? C3 C4 C9 C8 -177.9(2) . . . . ? C2 C3 C10 C11 -124.23(19) . . . . ? C4 C3 C10 C11 51.5(2) . . . . ? C2 C3 C10 C17 106.9(2) . . . . ? C4 C3 C10 C17 -77.4(2) . . . . ? C2 C3 C10 C20 -2.1(2) . . . . ? C4 C3 C10 C20 173.60(17) . . . . ? C3 C10 C11 C16 -128.4(2) . . . . ? C17 C10 C11 C16 2.1(3) . . . . ? C20 C10 C11 C16 116.0(2) . . . . ? C3 C10 C11 C12 50.4(2) . . . . ? C17 C10 C11 C12 -179.04(18) . . . . ? C20 C10 C11 C12 -65.1(2) . . . . ? C16 C11 C12 C13 0.8(3) . . . . ? C10 C11 C12 C13 -178.08(19) . . . . ? C11 C12 C13 C14 0.7(3) . . . . ? C12 C13 C14 C15 -1.7(4) . . . . ? C13 C14 C15 C16 1.2(4) . . . . ? C14 C15 C16 C11 0.3(4) . . . . ? C12 C11 C16 C15 -1.3(3) . . . . ? C10 C11 C16 C15 177.5(2) . . . . ? C3 C10 C17 C21 -47.1(2) . . . . ? C11 C10 C17 C21 -175.59(16) . . . . ? C20 C10 C17 C21 62.94(19) . . . . ? C3 C10 C17 C18 -148.76(17) . . . . ? C11 C10 C17 C18 82.80(19) . . . . ? C20 C10 C17 C18 -38.67(17) . . . . ? C21 C17 C18 O1 129.4(2) . . . . ? C10 C17 C18 O1 -118.1(2) . . . . ? C21 C17 C18 C19 -51.05(16) . . . . ? C10 C17 C18 C19 61.39(16) . . . . ? O1 C18 C19 C28 -128.0(2) . . . . ? C17 C18 C19 C28 52.54(16) . . . . ? O1 C18 C19 C20 120.9(2) . . . . ? C17 C18 C19 C20 -58.62(16) . . . . ? O2 C1 C20 C19 63.8(3) . . . . ? C2 C1 C20 C19 -116.30(19) . . . . ? O2 C1 C20 C10 178.4(2) . . . . ? C2 C1 C20 C10 -1.7(2) . . . . ? C28 C19 C20 C1 47.7(2) . . . . ? C18 C19 C20 C1 148.29(18) . . . . ? C28 C19 C20 C10 -66.7(2) . . . . ? C18 C19 C20 C10 33.87(18) . . . . ? C3 C10 C20 C1 2.24(19) . . . . ? C11 C10 C20 C1 122.59(18) . . . . ? C17 C10 C20 C1 -117.13(16) . . . . ? C3 C10 C20 C19 122.34(16) . . . . ? C11 C10 C20 C19 -117.31(17) . . . . ? C17 C10 C20 C19 2.97(19) . . . . ? C18 C17 C21 C28 31.1(2) . . . . ? C10 C17 C21 C28 -70.5(2) . . . . ? C18 C17 C21 C22 -149.78(18) . . . . ? C10 C17 C21 C22 108.6(2) . . . . ? C28 C21 C22 C27 51.3(3) . . . . ? C17 C21 C22 C27 -127.6(2) . . . . ? C28 C21 C22 C23 -130.0(2) . . . . ? C17 C21 C22 C23 51.1(3) . . . . ? C27 C22 C23 C24 -2.2(3) . . . . ? C21 C22 C23 C24 179.0(2) . . . . ? C22 C23 C24 C25 1.8(4) . . . . ? C23 C24 C25 C26 0.2(4) . . . . ? C24 C25 C26 C27 -1.7(4) . . . . ? C25 C26 C27 C22 1.2(3) . . . . ? C23 C22 C27 C26 0.7(3) . . . . ? C21 C22 C27 C26 179.5(2) . . . . ? C22 C21 C28 C29 9.6(4) . . . . ? C17 C21 C28 C29 -171.36(19) . . . . ? C22 C21 C28 C19 -176.22(19) . . . . ? C17 C21 C28 C19 2.8(2) . . . . ? C18 C19 C28 C21 -35.6(2) . . . . ? C20 C19 C28 C21 65.1(2) . . . . ? C18 C19 C28 C29 138.9(2) . . . . ? C20 C19 C28 C29 -120.3(2) . . . . ? C21 C28 C29 C34 -148.3(2) . . . . ? C19 C28 C29 C34 38.3(3) . . . . ? C21 C28 C29 C30 34.1(3) . . . . ? C19 C28 C29 C30 -139.3(2) . . . . ? C34 C29 C30 C31 0.4(3) . . . . ? C28 C29 C30 C31 178.1(2) . . . . ? C29 C30 C31 C32 0.4(4) . . . . ? C30 C31 C32 C33 -0.7(4) . . . . ? C31 C32 C33 C34 0.2(4) . . . . ? C32 C33 C34 C29 0.7(4) . . . . ? C30 C29 C34 C33 -1.0(3) . . . . ? C28 C29 C34 C33 -178.6(2) . . . . ? _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 0.175 _refine_diff_density_min -0.155 _refine_diff_density_rms 0.039 _database_code_depnum_ccdc_archive 'CCDC 966206' ####################################################################### # # 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_a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H20 O2' _chemical_formula_sum 'C18 H20 O2' _chemical_formula_weight 268.34 _chemical_absolute_configuration unk 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 P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 9.1769(18) _cell_length_b 10.289(2) _cell_length_c 14.620(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1380.4(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3122 _cell_measurement_theta_min 1.3929 _cell_measurement_theta_max 27.4836 _exptl_crystal_description block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.34 _exptl_crystal_size_min 0.32 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.291 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 576 _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7441 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'CrystalClear (Rigaku Inc., 2008)' _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 'Saturn724+ CCD' _diffrn_measurement_method '\w scans at fixed \c = 45\%' _diffrn_detector_area_resol_mean 28.5714 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7672 _diffrn_reflns_av_R_equivalents 0.0279 _diffrn_reflns_av_sigmaI/netI 0.0191 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.28 _diffrn_reflns_theta_max 27.49 _reflns_number_total 1814 _reflns_number_gt 1738 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2008)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2008)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2008)' _computing_structure_solution 'SHELX-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELX-97 (Sheldrick, 2008)' _computing_molecular_graphics ; Mercury: visualization and analysis of crystal structures, C. F. Macrae, P. R. Edgington, P. McCabe, E. Pidcock, G. P. Shields, R. Taylor, M. Towler and J. van de Streek, J. Appl. Cryst., 39, 453-457, 2006. ; _computing_publication_material 'SHELX-97 (Sheldrick, 2008)' _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^)+(0.0498P)^2^+0.2573P] 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 constr _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(3) _refine_ls_number_reflns 1814 _refine_ls_number_parameters 200 _refine_ls_number_restraints 66 _refine_ls_R_factor_all 0.0534 _refine_ls_R_factor_gt 0.0499 _refine_ls_wR_factor_ref 0.1232 _refine_ls_wR_factor_gt 0.1210 _refine_ls_goodness_of_fit_ref 1.168 _refine_ls_restrained_S_all 1.199 _refine_ls_shift/su_max 0.001 _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 1.1673(2) 0.4048(2) 0.40218(17) 0.0733(7) Uani 1 1 d . . . O2 O 0.6714(3) 0.4884(2) 0.60594(14) 0.0795(7) Uani 1 1 d . B . C1 C 0.8761(3) 0.5892(2) 0.36536(16) 0.0433(6) Uani 1 1 d . B . C2 C 0.8112(4) 0.6862(2) 0.30110(18) 0.0532(7) Uani 1 1 d D . . H2A H 0.7103 0.6644 0.2885 0.064 Uiso 1 1 calc R A 1 H2B H 0.8644 0.6868 0.2438 0.064 Uiso 1 1 calc R A 1 C3 C 0.8211(11) 0.8209(6) 0.3480(5) 0.0600(18) Uani 0.456(9) 1 d PDU B 1 H3B H 0.9212 0.8511 0.3461 0.072 Uiso 0.456(9) 1 calc PR B 1 H3A H 0.7618 0.8827 0.3144 0.072 Uiso 0.456(9) 1 calc PR B 1 C4 C 0.7702(9) 0.8166(9) 0.4468(5) 0.0654(19) Uani 0.456(9) 1 d PDU B 1 H4B H 0.7672 0.9040 0.4716 0.078 Uiso 0.456(9) 1 calc PR B 1 H4A H 0.6726 0.7806 0.4497 0.078 Uiso 0.456(9) 1 calc PR B 1 C3' C 0.7432(8) 0.8017(6) 0.3499(4) 0.0595(15) Uani 0.544(9) 1 d PDU B 2 H3'B H 0.7299 0.8725 0.3070 0.071 Uiso 0.544(9) 1 calc PR B 2 H3'A H 0.6482 0.7775 0.3736 0.071 Uiso 0.544(9) 1 calc PR B 2 C4' C 0.8392(9) 0.8458(6) 0.4275(5) 0.0608(16) Uani 0.544(9) 1 d PDU B 2 H4'A H 0.7937 0.9195 0.4574 0.073 Uiso 0.544(9) 1 calc PR B 2 H4'B H 0.9317 0.8748 0.4027 0.073 Uiso 0.544(9) 1 calc PR B 2 C5 C 0.8688(4) 0.7371(3) 0.5010(2) 0.0614(8) Uani 1 1 d D . . H5A H 0.8249 0.7193 0.5600 0.074 Uiso 1 1 calc R B 1 H5B H 0.9588 0.7844 0.5114 0.074 Uiso 1 1 calc R B 1 C6 C 0.9019(3) 0.6116(3) 0.45367(17) 0.0489(6) Uani 1 1 d . B . C7 C 0.9606(3) 0.4877(3) 0.49614(18) 0.0534(7) Uani 1 1 d . . . H7 H 1.0165 0.4969 0.5529 0.064 Uiso 1 1 calc R B . C8 C 1.0440(3) 0.4395(3) 0.4117(2) 0.0528(6) Uani 1 1 d . B . C9 C 0.9168(3) 0.4503(2) 0.34362(16) 0.0431(6) Uani 1 1 d . . . H9 H 0.9389 0.4307 0.2795 0.052 Uiso 1 1 calc R B . C10 C 0.8075(3) 0.3551(2) 0.39379(16) 0.0439(6) Uani 1 1 d . B . C11 C 0.8352(3) 0.3872(3) 0.49652(16) 0.0503(6) Uani 1 1 d . B . H11 H 0.8620 0.3091 0.5310 0.060 Uiso 1 1 calc R . . C12 C 0.6912(4) 0.4429(3) 0.52994(17) 0.0564(7) Uani 1 1 d . . . C13 C 0.5866(3) 0.4340(3) 0.45537(19) 0.0557(7) Uani 1 1 d . B . H13 H 0.4891 0.4577 0.4597 0.067 Uiso 1 1 calc R . . C14 C 0.6495(3) 0.3871(3) 0.37995(17) 0.0475(6) Uani 1 1 d . . . C15 C 0.5803(3) 0.3554(3) 0.29017(19) 0.0603(8) Uani 1 1 d . B . H15B H 0.6191 0.4118 0.2429 0.072 Uiso 1 1 calc R . . H15A H 0.4759 0.3692 0.2938 0.072 Uiso 1 1 calc R . . C16 C 0.6122(4) 0.2122(3) 0.2661(2) 0.0648(8) Uani 1 1 d . . . H16B H 0.5611 0.1559 0.3086 0.078 Uiso 1 1 calc R B . H16A H 0.5766 0.1938 0.2050 0.078 Uiso 1 1 calc R . . C17 C 0.7736(4) 0.1841(3) 0.2706(2) 0.0628(8) Uani 1 1 d . B . H17B H 0.8240 0.2368 0.2256 0.075 Uiso 1 1 calc R . . H17A H 0.7905 0.0935 0.2556 0.075 Uiso 1 1 calc R . . C18 C 0.8356(3) 0.2127(2) 0.36545(19) 0.0534(7) Uani 1 1 d . . . H18B H 0.9396 0.1961 0.3654 0.064 Uiso 1 1 calc R B . H18A H 0.7910 0.1549 0.4098 0.064 Uiso 1 1 calc R . . 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 0.0481(11) 0.0807(16) 0.0911(16) -0.0025(13) -0.0075(11) 0.0117(12) O2 0.0998(18) 0.0901(16) 0.0486(11) -0.0093(11) 0.0192(12) -0.0077(16) C1 0.0440(13) 0.0422(13) 0.0436(12) 0.0032(10) 0.0039(10) -0.0022(11) C2 0.0562(16) 0.0510(15) 0.0522(14) 0.0083(12) -0.0024(13) -0.0017(14) C3 0.055(4) 0.046(3) 0.079(4) 0.009(3) -0.010(4) 0.005(3) C4 0.045(3) 0.061(4) 0.091(4) -0.017(3) -0.002(3) 0.011(3) C3' 0.051(3) 0.054(3) 0.074(3) 0.001(2) -0.006(3) 0.003(3) C4' 0.052(3) 0.047(3) 0.083(4) -0.010(3) -0.008(3) 0.006(3) C5 0.0720(19) 0.0536(15) 0.0586(15) -0.0130(13) 0.0054(15) -0.0055(15) C6 0.0539(15) 0.0472(14) 0.0457(13) -0.0003(11) -0.0001(12) -0.0034(13) C7 0.0623(16) 0.0534(15) 0.0444(13) 0.0017(12) -0.0118(12) -0.0024(14) C8 0.0526(16) 0.0474(14) 0.0584(15) 0.0045(12) -0.0032(13) 0.0001(13) C9 0.0452(13) 0.0453(13) 0.0389(11) 0.0008(10) 0.0033(10) -0.0002(11) C10 0.0498(14) 0.0423(12) 0.0396(12) 0.0032(9) 0.0014(11) -0.0001(12) C11 0.0650(16) 0.0473(13) 0.0386(12) 0.0083(10) -0.0043(12) 0.0001(13) C12 0.0721(19) 0.0536(15) 0.0435(13) 0.0053(11) 0.0143(13) -0.0064(15) C13 0.0508(15) 0.0586(16) 0.0577(15) 0.0057(13) 0.0099(13) 0.0000(14) C14 0.0510(15) 0.0430(13) 0.0485(13) 0.0060(11) 0.0007(11) -0.0045(12) C15 0.0514(17) 0.0732(19) 0.0562(15) 0.0044(14) -0.0068(13) -0.0030(16) C16 0.073(2) 0.0675(19) 0.0542(16) -0.0039(14) -0.0040(15) -0.0201(17) C17 0.081(2) 0.0474(15) 0.0601(17) -0.0072(13) 0.0089(16) -0.0043(16) C18 0.0601(17) 0.0419(13) 0.0581(15) 0.0039(11) 0.0017(14) 0.0035(13) _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 C8 1.195(4) . ? O2 C12 1.219(3) . ? C1 C6 1.333(3) . ? C1 C2 1.495(3) . ? C1 C9 1.511(3) . ? C2 C3' 1.521(6) . ? C2 C3 1.550(7) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.519(8) . ? C3 H3B 0.9700 . ? C3 H3A 0.9700 . ? C4 C5 1.454(7) . ? C4 H4B 0.9700 . ? C4 H4A 0.9700 . ? C3' C4' 1.506(7) . ? C3' H3'B 0.9700 . ? C3' H3'A 0.9700 . ? C4' C5 1.574(6) . ? C4' H4'A 0.9700 . ? C4' H4'B 0.9700 . ? C5 C6 1.496(4) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C7 1.517(4) . ? C7 C8 1.535(4) . ? C7 C11 1.547(4) . ? C7 H7 0.9800 . ? C8 C9 1.537(4) . ? C9 C10 1.583(3) . ? C9 H9 0.9800 . ? C10 C14 1.501(4) . ? C10 C18 1.544(4) . ? C10 C11 1.559(3) . ? C11 C12 1.521(4) . ? C11 H11 0.9800 . ? C12 C13 1.455(4) . ? C13 C14 1.334(4) . ? C13 H13 0.9300 . ? C14 C15 1.494(4) . ? C15 C16 1.543(5) . ? C15 H15B 0.9700 . ? C15 H15A 0.9700 . ? C16 C17 1.511(5) . ? C16 H16B 0.9700 . ? C16 H16A 0.9700 . ? C17 C18 1.528(4) . ? C17 H17B 0.9700 . ? C17 H17A 0.9700 . ? C18 H18B 0.9700 . ? C18 H18A 0.9700 . ? 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 C2 124.3(2) . . ? C6 C1 C9 108.9(2) . . ? C2 C1 C9 126.7(2) . . ? C1 C2 C3' 113.0(3) . . ? C1 C2 C3 107.2(3) . . ? C3' C2 C3 28.0(3) . . ? C1 C2 H2A 110.3 . . ? C3' C2 H2A 83.0 . . ? C3 C2 H2A 110.3 . . ? C1 C2 H2B 110.3 . . ? C3' C2 H2B 127.4 . . ? C3 C2 H2B 110.3 . . ? H2A C2 H2B 108.5 . . ? C4 C3 C2 112.1(6) . . ? C4 C3 H3B 109.2 . . ? C2 C3 H3B 109.2 . . ? C4 C3 H3A 109.2 . . ? C2 C3 H3A 109.2 . . ? H3B C3 H3A 107.9 . . ? C5 C4 C3 110.1(6) . . ? C5 C4 H4B 109.6 . . ? C3 C4 H4B 109.6 . . ? C5 C4 H4A 109.6 . . ? C3 C4 H4A 109.6 . . ? H4B C4 H4A 108.2 . . ? C4' C3' C2 110.4(5) . . ? C4' C3' H3'B 109.6 . . ? C2 C3' H3'B 109.6 . . ? C4' C3' H3'A 109.6 . . ? C2 C3' H3'A 109.6 . . ? H3'B C3' H3'A 108.1 . . ? C3' C4' C5 113.6(5) . . ? C3' C4' H4'A 108.8 . . ? C5 C4' H4'A 108.8 . . ? C3' C4' H4'B 108.8 . . ? C5 C4' H4'B 108.8 . . ? H4'A C4' H4'B 107.7 . . ? C4 C5 C6 111.1(4) . . ? C4 C5 C4' 28.5(3) . . ? C6 C5 C4' 109.4(3) . . ? C4 C5 H5A 109.4 . . ? C6 C5 H5A 109.4 . . ? C4' C5 H5A 132.1 . . ? C4 C5 H5B 109.4 . . ? C6 C5 H5B 109.4 . . ? C4' C5 H5B 84.1 . . ? H5A C5 H5B 108.0 . . ? C1 C6 C5 124.2(3) . . ? C1 C6 C7 108.3(2) . . ? C5 C6 C7 127.4(2) . . ? C6 C7 C8 96.8(2) . . ? C6 C7 C11 107.4(2) . . ? C8 C7 C11 99.1(2) . . ? C6 C7 H7 116.8 . . ? C8 C7 H7 116.8 . . ? C11 C7 H7 116.8 . . ? O1 C8 C7 131.5(3) . . ? O1 C8 C9 131.7(3) . . ? C7 C8 C9 96.8(2) . . ? C1 C9 C8 96.8(2) . . ? C1 C9 C10 109.35(19) . . ? C8 C9 C10 97.86(19) . . ? C1 C9 H9 116.6 . . ? C8 C9 H9 116.6 . . ? C10 C9 H9 116.6 . . ? C14 C10 C18 109.5(2) . . ? C14 C10 C11 103.9(2) . . ? C18 C10 C11 115.6(2) . . ? C14 C10 C9 114.5(2) . . ? C18 C10 C9 110.9(2) . . ? C11 C10 C9 102.2(2) . . ? C12 C11 C7 113.3(2) . . ? C12 C11 C10 104.4(2) . . ? C7 C11 C10 105.0(2) . . ? C12 C11 H11 111.3 . . ? C7 C11 H11 111.3 . . ? C10 C11 H11 111.3 . . ? O2 C12 C13 127.5(3) . . ? O2 C12 C11 124.5(3) . . ? C13 C12 C11 108.0(2) . . ? C14 C13 C12 110.9(3) . . ? C14 C13 H13 124.5 . . ? C12 C13 H13 124.5 . . ? C13 C14 C15 128.4(3) . . ? C13 C14 C10 112.7(2) . . ? C15 C14 C10 118.7(2) . . ? C14 C15 C16 109.2(3) . . ? C14 C15 H15B 109.8 . . ? C16 C15 H15B 109.8 . . ? C14 C15 H15A 109.8 . . ? C16 C15 H15A 109.8 . . ? H15B C15 H15A 108.3 . . ? C17 C16 C15 111.0(3) . . ? C17 C16 H16B 109.4 . . ? C15 C16 H16B 109.4 . . ? C17 C16 H16A 109.4 . . ? C15 C16 H16A 109.4 . . ? H16B C16 H16A 108.0 . . ? C16 C17 C18 111.5(3) . . ? C16 C17 H17B 109.3 . . ? C18 C17 H17B 109.3 . . ? C16 C17 H17A 109.3 . . ? C18 C17 H17A 109.3 . . ? H17B C17 H17A 108.0 . . ? C17 C18 C10 111.4(2) . . ? C17 C18 H18B 109.4 . . ? C10 C18 H18B 109.4 . . ? C17 C18 H18A 109.4 . . ? C10 C18 H18A 109.4 . . ? H18B C18 H18A 108.0 . . ? 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 C6 C1 C2 C3' -13.9(5) . . . . ? C9 C1 C2 C3' 163.1(4) . . . . ? C6 C1 C2 C3 15.2(5) . . . . ? C9 C1 C2 C3 -167.7(4) . . . . ? C1 C2 C3 C4 -46.8(8) . . . . ? C3' C2 C3 C4 60.0(8) . . . . ? C2 C3 C4 C5 65.9(10) . . . . ? C1 C2 C3' C4' 41.9(7) . . . . ? C3 C2 C3' C4' -41.5(7) . . . . ? C2 C3' C4' C5 -58.7(9) . . . . ? C3 C4 C5 C6 -46.8(9) . . . . ? C3 C4 C5 C4' 45.4(7) . . . . ? C3' C4' C5 C4 -54.7(8) . . . . ? C3' C4' C5 C6 43.9(8) . . . . ? C2 C1 C6 C5 0.2(5) . . . . ? C9 C1 C6 C5 -177.3(3) . . . . ? C2 C1 C6 C7 177.1(3) . . . . ? C9 C1 C6 C7 -0.4(3) . . . . ? C4 C5 C6 C1 15.9(6) . . . . ? C4' C5 C6 C1 -14.5(5) . . . . ? C4 C5 C6 C7 -160.4(5) . . . . ? C4' C5 C6 C7 169.2(4) . . . . ? C1 C6 C7 C8 33.7(3) . . . . ? C5 C6 C7 C8 -149.6(3) . . . . ? C1 C6 C7 C11 -68.1(3) . . . . ? C5 C6 C7 C11 108.7(3) . . . . ? C6 C7 C8 O1 128.3(4) . . . . ? C11 C7 C8 O1 -122.8(3) . . . . ? C6 C7 C8 C9 -51.9(2) . . . . ? C11 C7 C8 C9 57.1(2) . . . . ? C6 C1 C9 C8 -33.0(3) . . . . ? C2 C1 C9 C8 149.6(3) . . . . ? C6 C1 C9 C10 67.9(3) . . . . ? C2 C1 C9 C10 -109.6(3) . . . . ? O1 C8 C9 C1 -128.5(3) . . . . ? C7 C8 C9 C1 51.6(2) . . . . ? O1 C8 C9 C10 120.8(3) . . . . ? C7 C8 C9 C10 -59.1(2) . . . . ? C1 C9 C10 C14 49.7(3) . . . . ? C8 C9 C10 C14 149.8(2) . . . . ? C1 C9 C10 C18 174.2(2) . . . . ? C8 C9 C10 C18 -85.7(2) . . . . ? C1 C9 C10 C11 -62.0(3) . . . . ? C8 C9 C10 C11 38.2(2) . . . . ? C6 C7 C11 C12 -45.7(3) . . . . ? C8 C7 C11 C12 -145.9(2) . . . . ? C6 C7 C11 C10 67.6(3) . . . . ? C8 C7 C11 C10 -32.6(2) . . . . ? C14 C10 C11 C12 -3.5(2) . . . . ? C18 C10 C11 C12 -123.5(2) . . . . ? C9 C10 C11 C12 115.9(2) . . . . ? C14 C10 C11 C7 -122.9(2) . . . . ? C18 C10 C11 C7 117.1(3) . . . . ? C9 C10 C11 C7 -3.5(3) . . . . ? C7 C11 C12 O2 -61.1(4) . . . . ? C10 C11 C12 O2 -174.7(3) . . . . ? C7 C11 C12 C13 117.9(2) . . . . ? C10 C11 C12 C13 4.2(3) . . . . ? O2 C12 C13 C14 175.5(3) . . . . ? C11 C12 C13 C14 -3.4(3) . . . . ? C12 C13 C14 C15 176.2(3) . . . . ? C12 C13 C14 C10 1.1(3) . . . . ? C18 C10 C14 C13 125.7(3) . . . . ? C11 C10 C14 C13 1.6(3) . . . . ? C9 C10 C14 C13 -109.0(3) . . . . ? C18 C10 C14 C15 -49.9(3) . . . . ? C11 C10 C14 C15 -174.0(2) . . . . ? C9 C10 C14 C15 75.4(3) . . . . ? C13 C14 C15 C16 -123.8(3) . . . . ? C10 C14 C15 C16 51.1(3) . . . . ? C14 C15 C16 C17 -53.0(3) . . . . ? C15 C16 C17 C18 58.6(3) . . . . ? C16 C17 C18 C10 -57.3(3) . . . . ? C14 C10 C18 C17 50.3(3) . . . . ? C11 C10 C18 C17 167.2(2) . . . . ? C9 C10 C18 C17 -77.0(3) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.159 _refine_diff_density_min -0.106 _refine_diff_density_rms 0.029 _database_code_depnum_ccdc_archive 'CCDC 966207' ####################################################################### # # 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_13nov07f _audit_creation_date 2013-11-13 _audit_creation_method ; Olex2 1.2 (compiled Apr 23 2013 17:54:37, GUI svn.r4466) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C40 H36' _chemical_formula_sum 'C40 H36' _chemical_formula_weight 516.69 _chemical_melting_point ? 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' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 1 21/n 1' _space_group_name_Hall '-P 2yn' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 12.6639(4) _cell_length_b 16.9311(6) _cell_length_c 13.6040(4) _cell_angle_alpha 90 _cell_angle_beta 92.886(3) _cell_angle_gamma 90 _cell_volume 2913.20(16) _cell_formula_units_Z 4 _cell_measurement_reflns_used ? _cell_measurement_temperature 180.15 _cell_measurement_theta_max ? _cell_measurement_theta_min ? _exptl_absorpt_coefficient_mu 0.066 _exptl_absorpt_correction_T_max ? _exptl_absorpt_correction_T_min 0.990 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ? _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.178 _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_description block _exptl_crystal_F_000 1104 _exptl_crystal_preparation ? _exptl_crystal_recrystallization_method ? _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.1 _exptl_special_details ; ? ; _exptl_transmission_factor_max ? _exptl_transmission_factor_min ? _diffrn_reflns_av_R_equivalents 0.0281 _diffrn_reflns_av_unetI/netI 0.0321 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.999 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 15003 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.999 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 26.014 _diffrn_reflns_theta_min 2.835 _diffrn_ambient_temperature 180.15 _diffrn_detector_area_resol_mean ? _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source ? _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_full . _reflns_Friedel_fraction_max . _reflns_number_gt 4525 _reflns_number_total 5737 _reflns_special_details ; Reflections were merged by SHELXL according to the crystal class for the calculation of statistics and refinement. _reflns_Friedel_fraction is defined as the number of unique Friedel pairs measured divided by the number that would be possible theoretically, ignoring centric projections and systematic absences. ; _reflns_threshold_expression 'I > 2\s(I)' _computing_cell_refinement ? _computing_data_collection ? _computing_data_reduction ? _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; XL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution 'SUPERFLIP, J. Appl. Cryst. (2007) 40, 786-790' _refine_diff_density_max 0.244 _refine_diff_density_min -0.192 _refine_diff_density_rms 0.037 _refine_ls_extinction_coef . _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.020 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 361 _refine_ls_number_reflns 5737 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0590 _refine_ls_R_factor_gt 0.0436 _refine_ls_restrained_S_all 1.020 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0399P)^2^+1.1189P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0997 _refine_ls_wR_factor_ref 0.1090 _refine_special_details ; ? ; _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups 2.a Secondary CH2 refined with riding coordinates: C15(H15A,H15B), C16(H16A,H16B), C17(H17A,H17B), C18(H18A,H18B), C31(H31A, H31B), C32(H32A,H32B), C33(H33A,H33B), C34(H34A,H34B) 2.b Aromatic/amide H refined with riding coordinates: C10(H10), C11(H11), C12(H12), C13(H13), C14(H14), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24), C26(H26), C27(H27), C28(H28), C29(H29), C30(H30), C36(H36), C37(H37), C38(H38), C39(H39), C40(H40) ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary iterative _atom_sites_solution_secondary ? 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_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.72602(11) 0.29452(8) 0.96211(10) 0.0247(3) Uani 1 1 d . . . . . C2 C 0.76712(11) 0.21634(8) 0.99764(10) 0.0244(3) Uani 1 1 d . . . . . C3 C 0.70421(11) 0.15688(8) 1.02134(10) 0.0249(3) Uani 1 1 d . . . . . C4 C 0.58671(11) 0.16531(8) 1.01715(10) 0.0246(3) Uani 1 1 d . . . . . C5 C 0.52989(11) 0.17488(8) 0.93223(10) 0.0245(3) Uani 1 1 d . . . . . C6 C 0.58024(11) 0.17655(8) 0.83564(10) 0.0247(3) Uani 1 1 d . . . . . C7 C 0.64319(11) 0.23517(8) 0.80912(10) 0.0251(3) Uani 1 1 d . . . . . C8 C 0.66905(11) 0.30316(8) 0.87614(10) 0.0252(3) Uani 1 1 d . . . . . C9 C 0.75347(11) 0.36250(8) 1.02893(10) 0.0260(3) Uani 1 1 d . . . . . C10 C 0.78951(12) 0.43479(9) 0.99542(11) 0.0319(3) Uani 1 1 d . . . . . H10 H 0.8001 0.4418 0.9273 0.038 Uiso 1 1 calc R U . . . C11 C 0.81008(13) 0.49651(9) 1.05991(12) 0.0374(4) Uani 1 1 d . . . . . H11 H 0.8347 0.5455 1.0358 0.045 Uiso 1 1 calc R U . . . C12 C 0.79517(13) 0.48756(9) 1.15901(11) 0.0362(4) Uani 1 1 d . . . . . H12 H 0.8074 0.5307 1.2028 0.043 Uiso 1 1 calc R U . . . C13 C 0.76246(12) 0.41571(9) 1.19412(11) 0.0336(4) Uani 1 1 d . . . . . H13 H 0.7534 0.4089 1.2625 0.040 Uiso 1 1 calc R U . . . C14 C 0.74287(11) 0.35369(9) 1.12993(10) 0.0296(3) Uani 1 1 d . . . . . H14 H 0.7218 0.3041 1.1550 0.035 Uiso 1 1 calc R U . . . C15 C 0.88666(12) 0.20999(9) 1.01199(11) 0.0330(3) Uani 1 1 d . . . . . H15A H 0.9169 0.1999 0.9474 0.040 Uiso 1 1 calc R U . . . H15B H 0.9151 0.2610 1.0370 0.040 Uiso 1 1 calc R U . . . C16 C 0.92181(13) 0.14506(10) 1.08276(13) 0.0413(4) Uani 1 1 d . . . . . H16A H 0.9992 0.1374 1.0806 0.050 Uiso 1 1 calc R U . . . H16B H 0.9057 0.1603 1.1507 0.050 Uiso 1 1 calc R U . . . C17 C 0.86576(13) 0.06933(10) 1.05544(13) 0.0406(4) Uani 1 1 d . . . . . H17A H 0.8906 0.0268 1.1009 0.049 Uiso 1 1 calc R U . . . H17B H 0.8827 0.0538 0.9879 0.049 Uiso 1 1 calc R U . . . C18 C 0.74713(12) 0.07911(9) 1.06067(12) 0.0358(4) Uani 1 1 d . . . . . H18A H 0.7117 0.0357 1.0231 0.043 Uiso 1 1 calc R U . . . H18B H 0.7285 0.0738 1.1302 0.043 Uiso 1 1 calc R U . . . C19 C 0.53875(11) 0.16715(8) 1.11569(10) 0.0259(3) Uani 1 1 d . . . . . C20 C 0.50844(11) 0.23867(9) 1.15491(11) 0.0298(3) Uani 1 1 d . . . . . H20 H 0.5159 0.2858 1.1181 0.036 Uiso 1 1 calc R U . . . C21 C 0.46753(13) 0.24214(9) 1.24690(12) 0.0358(4) Uani 1 1 d . . . . . H21 H 0.4471 0.2916 1.2728 0.043 Uiso 1 1 calc R U . . . C22 C 0.45604(13) 0.17427(10) 1.30152(11) 0.0358(4) Uani 1 1 d . . . . . H22 H 0.4284 0.1769 1.3651 0.043 Uiso 1 1 calc R U . . . C23 C 0.48484(12) 0.10285(9) 1.26320(11) 0.0332(4) Uani 1 1 d . . . . . H23 H 0.4766 0.0559 1.3002 0.040 Uiso 1 1 calc R U . . . C24 C 0.52575(12) 0.09907(9) 1.17092(11) 0.0300(3) Uani 1 1 d . . . . . H24 H 0.5452 0.0493 1.1450 0.036 Uiso 1 1 calc R U . . . C25 C 0.41187(11) 0.18390(8) 0.92705(10) 0.0264(3) Uani 1 1 d . . . . . C26 C 0.34629(12) 0.13455(9) 0.97854(11) 0.0320(3) Uani 1 1 d . . . . . H26 H 0.3765 0.0925 1.0167 0.038 Uiso 1 1 calc R U . . . C27 C 0.23806(13) 0.14567(10) 0.97509(12) 0.0392(4) Uani 1 1 d . . . . . H27 H 0.1946 0.1116 1.0111 0.047 Uiso 1 1 calc R U . . . C28 C 0.19289(13) 0.20613(11) 0.91955(13) 0.0422(4) Uani 1 1 d . . . . . H28 H 0.1186 0.2143 0.9181 0.051 Uiso 1 1 calc R U . . . C29 C 0.25610(13) 0.25456(10) 0.86620(13) 0.0405(4) Uani 1 1 d . . . . . H29 H 0.2252 0.2959 0.8273 0.049 Uiso 1 1 calc R U . . . C30 C 0.36491(12) 0.24310(9) 0.86914(11) 0.0328(3) Uani 1 1 d . . . . . H30 H 0.4077 0.2761 0.8311 0.039 Uiso 1 1 calc R U . . . C31 C 0.55271(12) 0.10720(9) 0.76938(11) 0.0315(3) Uani 1 1 d . . . . . H31A H 0.4766 0.0950 0.7735 0.038 Uiso 1 1 calc R U . . . H31B H 0.5932 0.0604 0.7935 0.038 Uiso 1 1 calc R U . . . C32 C 0.57584(14) 0.12152(10) 0.66263(11) 0.0403(4) Uani 1 1 d . . . . . H32A H 0.5743 0.0707 0.6267 0.048 Uiso 1 1 calc R U . . . H32B H 0.5206 0.1562 0.6318 0.048 Uiso 1 1 calc R U . . . C33 C 0.68284(14) 0.15980(10) 0.65497(12) 0.0417(4) Uani 1 1 d . . . . . H33A H 0.6975 0.1674 0.5848 0.050 Uiso 1 1 calc R U . . . H33B H 0.7383 0.1249 0.6849 0.050 Uiso 1 1 calc R U . . . C34 C 0.68570(12) 0.23893(9) 0.70722(10) 0.0321(3) Uani 1 1 d . . . . . H34A H 0.7596 0.2582 0.7126 0.039 Uiso 1 1 calc R U . . . H34B H 0.6435 0.2775 0.6671 0.039 Uiso 1 1 calc R U . . . C35 C 0.62293(12) 0.38091(9) 0.84352(11) 0.0306(3) Uani 1 1 d . . . . . C36 C 0.53774(13) 0.41143(9) 0.89158(13) 0.0386(4) Uani 1 1 d . . . . . H36 H 0.5112 0.3831 0.9454 0.046 Uiso 1 1 calc R U . . . C37 C 0.49061(16) 0.48194(11) 0.86307(16) 0.0541(5) Uani 1 1 d . . . . . H37 H 0.4325 0.5018 0.8971 0.065 Uiso 1 1 calc R U . . . C38 C 0.52824(19) 0.52305(11) 0.78540(17) 0.0619(6) Uani 1 1 d . . . . . H38 H 0.4956 0.5713 0.7650 0.074 Uiso 1 1 calc R U . . . C39 C 0.61297(19) 0.49467(11) 0.73700(14) 0.0581(6) Uani 1 1 d . . . . . H39 H 0.6393 0.5238 0.6838 0.070 Uiso 1 1 calc R U . . . C40 C 0.66066(15) 0.42343(10) 0.76531(12) 0.0423(4) Uani 1 1 d . . . . . H40 H 0.7189 0.4040 0.7312 0.051 Uiso 1 1 calc R U . . . 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 0.0238(7) 0.0262(7) 0.0243(7) 0.0021(6) 0.0013(6) -0.0044(6) C2 0.0249(7) 0.0283(7) 0.0197(6) 0.0002(6) -0.0021(5) -0.0010(6) C3 0.0266(7) 0.0270(7) 0.0208(7) 0.0003(6) -0.0013(5) 0.0002(6) C4 0.0266(7) 0.0203(7) 0.0269(7) 0.0021(6) 0.0004(6) -0.0022(6) C5 0.0255(7) 0.0198(7) 0.0281(7) 0.0008(6) -0.0007(6) -0.0029(6) C6 0.0233(7) 0.0268(7) 0.0236(7) 0.0002(6) -0.0042(6) 0.0013(6) C7 0.0243(7) 0.0275(7) 0.0229(7) 0.0023(6) -0.0041(6) 0.0014(6) C8 0.0258(7) 0.0266(7) 0.0233(7) 0.0034(6) 0.0009(6) -0.0042(6) C9 0.0227(7) 0.0285(7) 0.0263(7) 0.0011(6) -0.0043(6) -0.0020(6) C10 0.0367(9) 0.0330(8) 0.0255(7) 0.0016(6) -0.0028(6) -0.0073(7) C11 0.0447(10) 0.0294(8) 0.0375(9) 0.0007(7) -0.0043(7) -0.0106(7) C12 0.0392(9) 0.0354(9) 0.0333(8) -0.0085(7) -0.0064(7) -0.0036(7) C13 0.0333(8) 0.0422(9) 0.0248(7) -0.0014(7) -0.0042(6) -0.0016(7) C14 0.0283(8) 0.0327(8) 0.0271(7) 0.0046(6) -0.0043(6) -0.0037(6) C15 0.0258(8) 0.0379(9) 0.0348(8) 0.0028(7) -0.0034(6) -0.0033(6) C16 0.0293(8) 0.0503(10) 0.0430(9) 0.0072(8) -0.0089(7) 0.0028(7) C17 0.0368(9) 0.0389(9) 0.0458(10) 0.0079(8) -0.0025(7) 0.0100(7) C18 0.0326(9) 0.0307(8) 0.0440(9) 0.0093(7) -0.0007(7) 0.0014(7) C19 0.0222(7) 0.0290(7) 0.0262(7) 0.0020(6) -0.0023(6) -0.0024(6) C20 0.0289(8) 0.0268(7) 0.0333(8) 0.0031(6) -0.0011(6) -0.0018(6) C21 0.0377(9) 0.0319(8) 0.0382(8) -0.0070(7) 0.0061(7) 0.0002(7) C22 0.0364(9) 0.0421(9) 0.0295(8) -0.0025(7) 0.0078(7) -0.0036(7) C23 0.0368(9) 0.0320(8) 0.0311(8) 0.0057(7) 0.0047(7) -0.0019(7) C24 0.0338(8) 0.0257(7) 0.0307(8) 0.0007(6) 0.0039(6) 0.0002(6) C25 0.0264(7) 0.0273(7) 0.0252(7) -0.0051(6) -0.0019(6) -0.0020(6) C26 0.0298(8) 0.0357(8) 0.0302(8) -0.0001(7) -0.0010(6) -0.0051(7) C27 0.0285(8) 0.0525(10) 0.0367(9) -0.0058(8) 0.0030(7) -0.0082(8) C28 0.0247(8) 0.0561(11) 0.0456(10) -0.0137(9) -0.0009(7) 0.0031(8) C29 0.0356(9) 0.0406(9) 0.0441(9) -0.0045(8) -0.0093(7) 0.0096(7) C30 0.0326(8) 0.0332(8) 0.0321(8) 0.0002(7) -0.0047(6) -0.0015(7) C31 0.0343(8) 0.0289(8) 0.0308(8) -0.0031(6) -0.0019(6) -0.0040(6) C32 0.0580(11) 0.0339(9) 0.0283(8) -0.0049(7) -0.0044(7) -0.0039(8) C33 0.0552(11) 0.0406(9) 0.0302(8) -0.0010(7) 0.0109(8) 0.0015(8) C34 0.0344(8) 0.0359(8) 0.0260(7) 0.0026(6) 0.0023(6) -0.0028(7) C35 0.0370(8) 0.0255(7) 0.0279(7) 0.0019(6) -0.0124(6) -0.0075(6) C36 0.0380(9) 0.0307(8) 0.0461(9) -0.0008(7) -0.0101(7) -0.0010(7) C37 0.0529(12) 0.0350(10) 0.0722(13) -0.0044(10) -0.0202(10) 0.0057(9) C38 0.0800(16) 0.0307(10) 0.0711(14) 0.0035(10) -0.0357(12) 0.0060(10) C39 0.0951(17) 0.0354(10) 0.0411(10) 0.0131(8) -0.0254(11) -0.0187(11) C40 0.0615(12) 0.0326(9) 0.0316(8) 0.0047(7) -0.0099(8) -0.0109(8) _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 1.4937(19) . ? C1 C8 1.351(2) . ? C1 C9 1.497(2) . ? C2 C3 1.3334(19) . ? C2 C15 1.520(2) . ? C3 C4 1.493(2) . ? C3 C18 1.512(2) . ? C4 C5 1.340(2) . ? C4 C19 1.4996(18) . ? C5 C6 1.4894(18) . ? C5 C25 1.5006(19) . ? C6 C7 1.3342(19) . ? C6 C31 1.510(2) . ? C7 C8 1.495(2) . ? C7 C34 1.5135(19) . ? C8 C35 1.498(2) . ? C9 C10 1.391(2) . ? C9 C14 1.395(2) . ? C10 H10 0.9500 . ? C10 C11 1.381(2) . ? C11 H11 0.9500 . ? C11 C12 1.379(2) . ? C12 H12 0.9500 . ? C12 C13 1.378(2) . ? C13 H13 0.9500 . ? C13 C14 1.380(2) . ? C14 H14 0.9500 . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C15 C16 1.513(2) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C16 C17 1.503(2) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C17 C18 1.517(2) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 C20 1.385(2) . ? C19 C24 1.390(2) . ? C20 H20 0.9500 . ? C20 C21 1.380(2) . ? C21 H21 0.9500 . ? C21 C22 1.380(2) . ? C22 H22 0.9500 . ? C22 C23 1.373(2) . ? C23 H23 0.9500 . ? C23 C24 1.383(2) . ? C24 H24 0.9500 . ? C25 C26 1.392(2) . ? C25 C30 1.390(2) . ? C26 H26 0.9500 . ? C26 C27 1.382(2) . ? C27 H27 0.9500 . ? C27 C28 1.379(2) . ? C28 H28 0.9500 . ? C28 C29 1.378(2) . ? C29 H29 0.9500 . ? C29 C30 1.390(2) . ? C30 H30 0.9500 . ? C31 H31A 0.9900 . ? C31 H31B 0.9900 . ? C31 C32 1.515(2) . ? C32 H32A 0.9900 . ? C32 H32B 0.9900 . ? C32 C33 1.510(2) . ? C33 H33A 0.9900 . ? C33 H33B 0.9900 . ? C33 C34 1.516(2) . ? C34 H34A 0.9900 . ? C34 H34B 0.9900 . ? C35 C36 1.389(2) . ? C35 C40 1.389(2) . ? C36 H36 0.9500 . ? C36 C37 1.381(2) . ? C37 H37 0.9500 . ? C37 C38 1.371(3) . ? C38 H38 0.9500 . ? C38 C39 1.374(3) . ? C39 H39 0.9500 . ? C39 C40 1.394(3) . ? C40 H40 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 C9 114.74(12) . . ? C8 C1 C2 122.57(13) . . ? C8 C1 C9 122.69(13) . . ? C1 C2 C15 115.64(12) . . ? C3 C2 C1 122.99(13) . . ? C3 C2 C15 121.25(13) . . ? C2 C3 C4 121.68(13) . . ? C2 C3 C18 122.31(13) . . ? C4 C3 C18 115.88(12) . . ? C3 C4 C19 114.56(12) . . ? C5 C4 C3 122.37(12) . . ? C5 C4 C19 122.97(13) . . ? C4 C5 C6 121.86(13) . . ? C4 C5 C25 122.91(12) . . ? C6 C5 C25 115.23(12) . . ? C5 C6 C31 114.56(12) . . ? C7 C6 C5 122.74(13) . . ? C7 C6 C31 122.69(12) . . ? C6 C7 C8 121.58(12) . . ? C6 C7 C34 121.59(13) . . ? C8 C7 C34 116.70(12) . . ? C1 C8 C7 122.40(13) . . ? C1 C8 C35 122.34(13) . . ? C7 C8 C35 115.20(12) . . ? C10 C9 C1 123.21(12) . . ? C10 C9 C14 117.78(13) . . ? C14 C9 C1 119.01(12) . . ? C9 C10 H10 119.6 . . ? C11 C10 C9 120.82(14) . . ? C11 C10 H10 119.6 . . ? C10 C11 H11 119.8 . . ? C12 C11 C10 120.48(14) . . ? C12 C11 H11 119.8 . . ? C11 C12 H12 120.2 . . ? C13 C12 C11 119.61(14) . . ? C13 C12 H12 120.2 . . ? C12 C13 H13 120.0 . . ? C12 C13 C14 119.99(14) . . ? C14 C13 H13 120.0 . . ? C9 C14 H14 119.4 . . ? C13 C14 C9 121.23(14) . . ? C13 C14 H14 119.4 . . ? C2 C15 H15A 109.0 . . ? C2 C15 H15B 109.0 . . ? H15A C15 H15B 107.8 . . ? C16 C15 C2 113.09(12) . . ? C16 C15 H15A 109.0 . . ? C16 C15 H15B 109.0 . . ? C15 C16 H16A 109.7 . . ? C15 C16 H16B 109.7 . . ? H16A C16 H16B 108.2 . . ? C17 C16 C15 110.01(14) . . ? C17 C16 H16A 109.7 . . ? C17 C16 H16B 109.7 . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? C16 C17 C18 110.60(14) . . ? H17A C17 H17B 108.1 . . ? C18 C17 H17A 109.5 . . ? C18 C17 H17B 109.5 . . ? C3 C18 C17 114.69(13) . . ? C3 C18 H18A 108.6 . . ? C3 C18 H18B 108.6 . . ? C17 C18 H18A 108.6 . . ? C17 C18 H18B 108.6 . . ? H18A C18 H18B 107.6 . . ? C20 C19 C4 119.67(12) . . ? C20 C19 C24 118.29(13) . . ? C24 C19 C4 122.02(13) . . ? C19 C20 H20 119.6 . . ? C21 C20 C19 120.70(14) . . ? C21 C20 H20 119.6 . . ? C20 C21 H21 119.7 . . ? C20 C21 C22 120.50(14) . . ? C22 C21 H21 119.7 . . ? C21 C22 H22 120.3 . . ? C23 C22 C21 119.44(13) . . ? C23 C22 H22 120.3 . . ? C22 C23 H23 119.9 . . ? C22 C23 C24 120.26(14) . . ? C24 C23 H23 119.9 . . ? C19 C24 H24 119.6 . . ? C23 C24 C19 120.80(14) . . ? C23 C24 H24 119.6 . . ? C26 C25 C5 122.24(13) . . ? C30 C25 C5 119.79(13) . . ? C30 C25 C26 117.98(14) . . ? C25 C26 H26 119.4 . . ? C27 C26 C25 121.13(15) . . ? C27 C26 H26 119.4 . . ? C26 C27 H27 119.9 . . ? C28 C27 C26 120.19(15) . . ? C28 C27 H27 119.9 . . ? C27 C28 H28 120.2 . . ? C29 C28 C27 119.63(15) . . ? C29 C28 H28 120.2 . . ? C28 C29 H29 119.9 . . ? C28 C29 C30 120.21(16) . . ? C30 C29 H29 119.9 . . ? C25 C30 C29 120.81(15) . . ? C25 C30 H30 119.6 . . ? C29 C30 H30 119.6 . . ? C6 C31 H31A 108.9 . . ? C6 C31 H31B 108.9 . . ? C6 C31 C32 113.43(12) . . ? H31A C31 H31B 107.7 . . ? C32 C31 H31A 108.9 . . ? C32 C31 H31B 108.9 . . ? C31 C32 H32A 109.5 . . ? C31 C32 H32B 109.5 . . ? H32A C32 H32B 108.1 . . ? C33 C32 C31 110.62(14) . . ? C33 C32 H32A 109.5 . . ? C33 C32 H32B 109.5 . . ? C32 C33 H33A 109.6 . . ? C32 C33 H33B 109.6 . . ? C32 C33 C34 110.31(13) . . ? H33A C33 H33B 108.1 . . ? C34 C33 H33A 109.6 . . ? C34 C33 H33B 109.6 . . ? C7 C34 C33 113.02(12) . . ? C7 C34 H34A 109.0 . . ? C7 C34 H34B 109.0 . . ? C33 C34 H34A 109.0 . . ? C33 C34 H34B 109.0 . . ? H34A C34 H34B 107.8 . . ? C36 C35 C8 119.21(13) . . ? C36 C35 C40 118.22(15) . . ? C40 C35 C8 122.56(14) . . ? C35 C36 H36 119.2 . . ? C37 C36 C35 121.62(17) . . ? C37 C36 H36 119.2 . . ? C36 C37 H37 120.2 . . ? C38 C37 C36 119.6(2) . . ? C38 C37 H37 120.2 . . ? C37 C38 H38 119.9 . . ? C37 C38 C39 120.15(18) . . ? C39 C38 H38 119.9 . . ? C38 C39 H39 119.7 . . ? C38 C39 C40 120.53(18) . . ? C40 C39 H39 119.7 . . ? C35 C40 C39 119.93(18) . . ? C35 C40 H40 120.0 . . ? C39 C40 H40 120.0 . . ? _shelx_estimated_absorpt_T_max 0.993 _shelx_estimated_absorpt_T_min 0.990 _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _shelxl_version_number 2013-3 _database_code_depnum_ccdc_archive 'CCDC 971720'