Supplementary Material (ESI) for Dalton Transactions This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'J. Woollins' _publ_contact_author_address ; Department of Chemistry University of St Andrews St Andrews FIFE SCOTLAND KY16 9ST UNITED KINGDOM ; _publ_contact_author_email JDW3@ST-ANDREWS.AC.UK _publ_section_title ; Stereoselective Synthesis of Olefins by a Reductive Coupling Reaction ; loop_ _publ_author_name 'J. Woollins' 'Guoxiong Hua.' 'Yang Li.' 'A Slawin' # Attachment '17.cif' data_17 _database_code_depnum_ccdc_archive 'CCDC 614296' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C35 H25 P Se' _chemical_formula_sum 'C35 H25 P Se' _chemical_formula_weight 555.28 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0030 0.0020 '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' P P 0.1020 0.0940 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Se Se -0.0930 2.2260 '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 8.7786(16) _cell_length_b 12.928(3) _cell_length_c 13.292(3) _cell_angle_alpha 110.949(5) _cell_angle_beta 96.458(5) _cell_angle_gamma 106.949(5) _cell_volume 1307.3(5) _cell_formula_units_Z 2 _cell_measurement_temperature 93(2) _cell_measurement_reflns_used 3739 _cell_measurement_theta_min 1.71 _cell_measurement_theta_max 24.78 _exptl_crystal_description Prism _exptl_crystal_colour Brown _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.411 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 568 _exptl_absorpt_coefficient_mu 1.520 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8628 _exptl_absorpt_correction_T_max 0.9279 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 93(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator confocal _diffrn_measurement_device_type CCD _diffrn_measurement_method dtprofit.ref _diffrn_detector_area_resol_mean 0.83 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8762 _diffrn_reflns_av_R_equivalents 0.0522 _diffrn_reflns_av_sigmaI/netI 0.1470 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.51 _diffrn_reflns_theta_max 28.24 _reflns_number_total 4720 _reflns_number_gt 3071 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Corp., 2004)' _computing_cell_refinement 'CrystalClear (Rigaku Corp., 2004)' _computing_data_reduction 'CrystalClear (Rigaku Corp., 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics PLATON _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0280P)^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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4720 _refine_ls_number_parameters 334 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0930 _refine_ls_R_factor_gt 0.0563 _refine_ls_wR_factor_ref 0.1082 _refine_ls_wR_factor_gt 0.0926 _refine_ls_goodness_of_fit_ref 0.945 _refine_ls_restrained_S_all 0.945 _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 Se1 Se 0.07052(5) -0.03489(4) 0.32467(4) 0.03075(17) Uani 1 1 d . . . P1 P 0.24949(13) 0.12524(11) 0.34684(10) 0.0267(3) Uani 1 1 d . . . C1 C 0.2329(4) 0.1842(4) 0.2439(4) 0.0193(10) Uani 1 1 d . . . C2 C 0.2211(4) 0.1504(4) 0.1334(4) 0.0213(10) Uani 1 1 d . . . C3 C 0.1913(5) 0.2463(3) 0.1024(3) 0.0191(10) Uani 1 1 d . . . H3 H 0.0799 0.2126 0.0511 0.023 Uiso 1 1 calc R . . C4 C 0.1905(4) 0.3395(4) 0.2119(4) 0.0199(10) Uani 1 1 d . . . C5 C 0.2146(5) 0.3014(4) 0.2933(4) 0.0223(10) Uani 1 1 d . . . C6 C 0.2149(5) 0.3394(4) 0.4105(4) 0.0224(10) Uani 1 1 d . . . C7 C 0.2369(5) 0.2570(4) 0.4534(4) 0.0242(11) Uani 1 1 d . . . C8 C 0.2344(5) 0.2741(4) 0.5624(4) 0.0320(12) Uani 1 1 d . . . H8 H 0.2488 0.2178 0.5893 0.038 Uiso 1 1 calc R . . C9 C 0.2104(5) 0.3750(4) 0.6316(4) 0.0340(12) Uani 1 1 d . . . H9 H 0.2091 0.3880 0.7064 0.041 Uiso 1 1 calc R . . C10 C 0.1886(5) 0.4564(4) 0.5920(4) 0.0333(12) Uani 1 1 d . . . H10 H 0.1729 0.5251 0.6402 0.040 Uiso 1 1 calc R . . C11 C 0.1892(5) 0.4390(4) 0.4820(4) 0.0277(11) Uani 1 1 d . . . H11 H 0.1721 0.4951 0.4557 0.033 Uiso 1 1 calc R . . C12 C 0.4591(5) 0.1318(4) 0.3785(4) 0.0277(11) Uani 1 1 d . . . C13 C 0.4939(6) 0.0368(5) 0.3856(4) 0.0416(14) Uani 1 1 d . . . H13 H 0.4064 -0.0328 0.3749 0.050 Uiso 1 1 calc R . . C14 C 0.6545(6) 0.0412(5) 0.4079(4) 0.0447(14) Uani 1 1 d . . . H14 H 0.6766 -0.0255 0.4110 0.054 Uiso 1 1 calc R . . C15 C 0.7826(5) 0.1441(5) 0.4259(4) 0.0393(14) Uani 1 1 d . . . H15 H 0.8935 0.1499 0.4440 0.047 Uiso 1 1 calc R . . C16 C 0.7461(6) 0.2376(4) 0.4170(4) 0.0330(12) Uani 1 1 d . . . H16 H 0.8329 0.3077 0.4279 0.040 Uiso 1 1 calc R . . C17 C 0.5941(5) 0.2316(4) 0.3938(3) 0.0213(10) Uani 1 1 d . . . H17 H 0.5740 0.2974 0.3869 0.026 Uiso 1 1 calc R . . C18 C 0.2367(4) 0.0438(4) 0.0533(4) 0.0210(10) Uani 1 1 d . . . C19 C 0.3133(5) -0.0221(4) 0.0876(4) 0.0295(12) Uani 1 1 d . . . H19 H 0.3539 0.0011 0.1647 0.035 Uiso 1 1 calc R . . C20 C 0.3317(5) -0.1220(4) 0.0107(4) 0.0357(13) Uani 1 1 d . . . H20 H 0.3848 -0.1660 0.0354 0.043 Uiso 1 1 calc R . . C21 C 0.2720(5) -0.1562(4) -0.1015(4) 0.0296(12) Uani 1 1 d . . . H21 H 0.2851 -0.2237 -0.1540 0.036 Uiso 1 1 calc R . . C22 C 0.1943(5) -0.0938(4) -0.1376(4) 0.0262(11) Uani 1 1 d . . . H22 H 0.1525 -0.1185 -0.2148 0.031 Uiso 1 1 calc R . . C23 C 0.1765(5) 0.0057(4) -0.0613(4) 0.0222(10) Uani 1 1 d . . . H23 H 0.1227 0.0487 -0.0870 0.027 Uiso 1 1 calc R . . C24 C 0.3182(5) 0.2954(4) 0.0459(4) 0.0216(10) Uani 1 1 d . . . C25 C 0.4828(5) 0.3559(4) 0.1071(4) 0.0285(11) Uani 1 1 d . . . H25 H 0.5113 0.3674 0.1825 0.034 Uiso 1 1 calc R . . C26 C 0.6005(6) 0.3976(4) 0.0593(4) 0.0328(12) Uani 1 1 d . . . H26 H 0.7108 0.4386 0.1020 0.039 Uiso 1 1 calc R . . C27 C 0.5641(6) 0.3821(4) -0.0486(5) 0.0360(13) Uani 1 1 d . . . H27 H 0.6484 0.4124 -0.0806 0.043 Uiso 1 1 calc R . . C28 C 0.4020(6) 0.3214(4) -0.1122(4) 0.0400(13) Uani 1 1 d . . . H28 H 0.3757 0.3085 -0.1881 0.048 Uiso 1 1 calc R . . C29 C 0.2795(6) 0.2801(4) -0.0626(4) 0.0313(12) Uani 1 1 d . . . H29 H 0.1685 0.2412 -0.1043 0.038 Uiso 1 1 calc R . . C30 C 0.1790(5) 0.4533(4) 0.2203(4) 0.0214(10) Uani 1 1 d . . . C31 C 0.0595(5) 0.4585(4) 0.1459(4) 0.0260(11) Uani 1 1 d . . . H31 H -0.0178 0.3869 0.0895 0.031 Uiso 1 1 calc R . . C32 C 0.0511(5) 0.5668(4) 0.1528(4) 0.0323(12) Uani 1 1 d . . . H32 H -0.0317 0.5684 0.1014 0.039 Uiso 1 1 calc R . . C33 C 0.1638(6) 0.6726(4) 0.2347(4) 0.0350(13) Uani 1 1 d . . . H33 H 0.1580 0.7465 0.2400 0.042 Uiso 1 1 calc R . . C34 C 0.2845(6) 0.6686(4) 0.3082(4) 0.0322(12) Uani 1 1 d . . . H34 H 0.3626 0.7405 0.3638 0.039 Uiso 1 1 calc R . . C35 C 0.2929(5) 0.5619(4) 0.3020(4) 0.0263(11) Uani 1 1 d . . . H35 H 0.3765 0.5613 0.3535 0.032 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 Se1 0.0302(3) 0.0279(3) 0.0334(3) 0.0120(3) 0.0065(2) 0.0107(2) P1 0.0272(6) 0.0294(8) 0.0231(8) 0.0090(6) 0.0036(5) 0.0127(6) C1 0.015(2) 0.020(2) 0.021(3) 0.007(2) -0.0008(17) 0.0059(19) C2 0.017(2) 0.021(3) 0.024(3) 0.007(2) 0.0034(18) 0.0074(19) C3 0.020(2) 0.015(2) 0.017(3) 0.002(2) 0.0010(17) 0.0047(19) C4 0.014(2) 0.020(3) 0.021(3) 0.005(2) 0.0017(17) 0.0056(19) C5 0.017(2) 0.021(3) 0.022(3) 0.004(2) 0.0028(18) 0.0049(19) C6 0.020(2) 0.023(3) 0.017(3) 0.006(2) 0.0024(18) 0.001(2) C7 0.019(2) 0.029(3) 0.021(3) 0.007(2) 0.0056(18) 0.008(2) C8 0.036(3) 0.042(3) 0.022(3) 0.015(3) 0.007(2) 0.017(2) C9 0.040(3) 0.042(3) 0.018(3) 0.008(3) 0.007(2) 0.017(3) C10 0.030(3) 0.028(3) 0.029(3) -0.001(2) 0.009(2) 0.007(2) C11 0.032(2) 0.024(3) 0.022(3) 0.004(2) 0.005(2) 0.010(2) C12 0.035(3) 0.034(3) 0.018(3) 0.006(2) 0.007(2) 0.024(2) C13 0.035(3) 0.047(4) 0.044(4) 0.021(3) 0.008(2) 0.015(3) C14 0.047(3) 0.067(4) 0.050(4) 0.038(3) 0.020(3) 0.040(3) C15 0.024(3) 0.063(4) 0.024(3) 0.006(3) 0.004(2) 0.022(3) C16 0.040(3) 0.028(3) 0.023(3) 0.001(2) 0.013(2) 0.011(2) C17 0.018(2) 0.018(3) 0.012(2) -0.0033(19) 0.0004(17) -0.002(2) C18 0.016(2) 0.024(3) 0.024(3) 0.012(2) 0.0068(18) 0.005(2) C19 0.038(3) 0.027(3) 0.025(3) 0.009(2) 0.003(2) 0.020(2) C20 0.043(3) 0.036(3) 0.045(4) 0.023(3) 0.015(3) 0.028(3) C21 0.032(3) 0.025(3) 0.026(3) 0.000(2) 0.012(2) 0.011(2) C22 0.029(2) 0.025(3) 0.025(3) 0.007(2) 0.009(2) 0.013(2) C23 0.021(2) 0.020(3) 0.024(3) 0.009(2) 0.0005(18) 0.007(2) C24 0.027(2) 0.013(2) 0.022(3) 0.004(2) 0.0048(19) 0.006(2) C25 0.028(2) 0.022(3) 0.033(3) 0.008(2) 0.004(2) 0.010(2) C26 0.035(3) 0.020(3) 0.045(4) 0.010(3) 0.018(2) 0.013(2) C27 0.041(3) 0.024(3) 0.051(4) 0.016(3) 0.028(3) 0.017(2) C28 0.060(3) 0.047(3) 0.031(3) 0.025(3) 0.021(3) 0.031(3) C29 0.041(3) 0.023(3) 0.026(3) 0.008(2) 0.004(2) 0.010(2) C30 0.022(2) 0.026(3) 0.020(3) 0.011(2) 0.0086(18) 0.011(2) C31 0.018(2) 0.024(3) 0.035(3) 0.013(2) 0.0037(19) 0.007(2) C32 0.026(2) 0.032(3) 0.040(3) 0.015(3) 0.008(2) 0.013(2) C33 0.046(3) 0.029(3) 0.045(4) 0.020(3) 0.022(3) 0.024(3) C34 0.049(3) 0.017(3) 0.024(3) 0.003(2) 0.017(2) 0.006(2) C35 0.030(2) 0.022(3) 0.021(3) 0.004(2) 0.0021(19) 0.008(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Se1 P1 2.0986(13) . ? P1 C1 1.800(4) . ? P1 C12 1.811(4) . ? P1 C7 1.828(5) . ? C1 C2 1.356(6) . ? C1 C5 1.486(6) . ? C2 C18 1.465(6) . ? C2 C3 1.519(6) . ? C3 C4 1.524(6) . ? C3 C24 1.525(6) . ? C3 H3 1.0000 . ? C4 C5 1.359(6) . ? C4 C30 1.470(6) . ? C5 C6 1.456(6) . ? C6 C11 1.398(6) . ? C6 C7 1.423(6) . ? C7 C8 1.388(6) . ? C8 C9 1.392(6) . ? C8 H8 0.9500 . ? C9 C10 1.382(6) . ? C9 H9 0.9500 . ? C10 C11 1.399(6) . ? C10 H10 0.9500 . ? C11 H11 0.9500 . ? C12 C13 1.380(6) . ? C12 C17 1.406(6) . ? C13 C14 1.388(6) . ? C13 H13 0.9500 . ? C14 C15 1.390(6) . ? C14 H14 0.9500 . ? C15 C16 1.377(6) . ? C15 H15 0.9500 . ? C16 C17 1.309(6) . ? C16 H16 0.9500 . ? C17 H17 0.9500 . ? C18 C19 1.388(6) . ? C18 C23 1.404(5) . ? C19 C20 1.397(6) . ? C19 H19 0.9500 . ? C20 C21 1.383(6) . ? C20 H20 0.9500 . ? C21 C22 1.368(6) . ? C21 H21 0.9500 . ? C22 C23 1.388(6) . ? C22 H22 0.9500 . ? C23 H23 0.9500 . ? C24 C29 1.371(6) . ? C24 C25 1.408(5) . ? C25 C26 1.353(6) . ? C25 H25 0.9500 . ? C26 C27 1.362(6) . ? C26 H26 0.9500 . ? C27 C28 1.400(6) . ? C27 H27 0.9500 . ? C28 C29 1.399(6) . ? C28 H28 0.9500 . ? C29 H29 0.9500 . ? C30 C31 1.392(5) . ? C30 C35 1.413(6) . ? C31 C32 1.395(6) . ? C31 H31 0.9500 . ? C32 C33 1.392(6) . ? C32 H32 0.9500 . ? C33 C34 1.384(6) . ? C33 H33 0.9500 . ? C34 C35 1.376(6) . ? C34 H34 0.9500 . ? C35 H35 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 C1 P1 C12 107.27(19) . . ? C1 P1 C7 91.3(2) . . ? C12 P1 C7 106.9(2) . . ? C1 P1 Se1 119.56(13) . . ? C12 P1 Se1 114.64(16) . . ? C7 P1 Se1 114.37(14) . . ? C2 C1 C5 110.5(4) . . ? C2 C1 P1 139.0(4) . . ? C5 C1 P1 110.3(3) . . ? C1 C2 C18 128.9(4) . . ? C1 C2 C3 107.9(4) . . ? C18 C2 C3 123.2(4) . . ? C2 C3 C4 104.1(4) . . ? C2 C3 C24 113.0(3) . . ? C4 C3 C24 113.3(3) . . ? C2 C3 H3 108.8 . . ? C4 C3 H3 108.8 . . ? C24 C3 H3 108.8 . . ? C5 C4 C30 129.5(4) . . ? C5 C4 C3 108.7(4) . . ? C30 C4 C3 121.7(4) . . ? C4 C5 C6 137.6(4) . . ? C4 C5 C1 108.8(4) . . ? C6 C5 C1 113.4(4) . . ? C11 C6 C7 117.7(4) . . ? C11 C6 C5 129.6(4) . . ? C7 C6 C5 112.7(4) . . ? C8 C7 C6 121.8(4) . . ? C8 C7 P1 125.6(4) . . ? C6 C7 P1 112.4(3) . . ? C7 C8 C9 119.0(5) . . ? C7 C8 H8 120.5 . . ? C9 C8 H8 120.5 . . ? C10 C9 C8 120.4(5) . . ? C10 C9 H9 119.8 . . ? C8 C9 H9 119.8 . . ? C9 C10 C11 120.9(5) . . ? C9 C10 H10 119.5 . . ? C11 C10 H10 119.5 . . ? C6 C11 C10 120.2(5) . . ? C6 C11 H11 119.9 . . ? C10 C11 H11 119.9 . . ? C13 C12 C17 116.6(4) . . ? C13 C12 P1 121.3(4) . . ? C17 C12 P1 122.1(4) . . ? C12 C13 C14 121.2(5) . . ? C12 C13 H13 119.4 . . ? C14 C13 H13 119.4 . . ? C13 C14 C15 119.3(5) . . ? C13 C14 H14 120.3 . . ? C15 C14 H14 120.3 . . ? C16 C15 C14 118.8(4) . . ? C16 C15 H15 120.6 . . ? C14 C15 H15 120.6 . . ? C17 C16 C15 121.3(4) . . ? C17 C16 H16 119.4 . . ? C15 C16 H16 119.4 . . ? C16 C17 C12 122.7(5) . . ? C16 C17 H17 118.6 . . ? C12 C17 H17 118.6 . . ? C19 C18 C23 117.7(4) . . ? C19 C18 C2 121.4(4) . . ? C23 C18 C2 120.9(4) . . ? C18 C19 C20 121.1(5) . . ? C18 C19 H19 119.4 . . ? C20 C19 H19 119.4 . . ? C21 C20 C19 119.5(4) . . ? C21 C20 H20 120.2 . . ? C19 C20 H20 120.2 . . ? C22 C21 C20 120.5(5) . . ? C22 C21 H21 119.7 . . ? C20 C21 H21 119.7 . . ? C21 C22 C23 120.0(4) . . ? C21 C22 H22 120.0 . . ? C23 C22 H22 120.0 . . ? C22 C23 C18 121.1(4) . . ? C22 C23 H23 119.4 . . ? C18 C23 H23 119.4 . . ? C29 C24 C25 118.9(4) . . ? C29 C24 C3 122.8(4) . . ? C25 C24 C3 118.3(4) . . ? C26 C25 C24 120.4(5) . . ? C26 C25 H25 119.8 . . ? C24 C25 H25 119.8 . . ? C25 C26 C27 121.4(5) . . ? C25 C26 H26 119.3 . . ? C27 C26 H26 119.3 . . ? C26 C27 C28 119.8(4) . . ? C26 C27 H27 120.1 . . ? C28 C27 H27 120.1 . . ? C29 C28 C27 119.1(5) . . ? C29 C28 H28 120.5 . . ? C27 C28 H28 120.5 . . ? C24 C29 C28 120.5(4) . . ? C24 C29 H29 119.7 . . ? C28 C29 H29 119.7 . . ? C31 C30 C35 117.5(4) . . ? C31 C30 C4 121.4(4) . . ? C35 C30 C4 121.1(4) . . ? C30 C31 C32 121.2(4) . . ? C30 C31 H31 119.4 . . ? C32 C31 H31 119.4 . . ? C33 C32 C31 120.1(4) . . ? C33 C32 H32 119.9 . . ? C31 C32 H32 119.9 . . ? C34 C33 C32 119.2(5) . . ? C34 C33 H33 120.4 . . ? C32 C33 H33 120.4 . . ? C35 C34 C33 120.9(4) . . ? C35 C34 H34 119.6 . . ? C33 C34 H34 119.6 . . ? C34 C35 C30 121.1(4) . . ? C34 C35 H35 119.4 . . ? C30 C35 H35 119.4 . . ? 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 C12 P1 C1 C2 76.5(5) . . . . ? C7 P1 C1 C2 -175.4(4) . . . . ? Se1 P1 C1 C2 -56.3(5) . . . . ? C12 P1 C1 C5 -109.4(3) . . . . ? C7 P1 C1 C5 -1.3(3) . . . . ? Se1 P1 C1 C5 117.9(2) . . . . ? C5 C1 C2 C18 178.0(3) . . . . ? P1 C1 C2 C18 -7.9(7) . . . . ? C5 C1 C2 C3 -0.7(4) . . . . ? P1 C1 C2 C3 173.5(3) . . . . ? C1 C2 C3 C4 0.8(4) . . . . ? C18 C2 C3 C4 -178.0(3) . . . . ? C1 C2 C3 C24 124.1(4) . . . . ? C18 C2 C3 C24 -54.7(5) . . . . ? C2 C3 C4 C5 -0.6(4) . . . . ? C24 C3 C4 C5 -123.7(4) . . . . ? C2 C3 C4 C30 174.7(3) . . . . ? C24 C3 C4 C30 51.6(5) . . . . ? C30 C4 C5 C6 11.2(8) . . . . ? C3 C4 C5 C6 -174.0(4) . . . . ? C30 C4 C5 C1 -174.6(4) . . . . ? C3 C4 C5 C1 0.2(4) . . . . ? C2 C1 C5 C4 0.3(4) . . . . ? P1 C1 C5 C4 -175.6(3) . . . . ? C2 C1 C5 C6 176.1(3) . . . . ? P1 C1 C5 C6 0.1(4) . . . . ? C4 C5 C6 C11 -0.9(8) . . . . ? C1 C5 C6 C11 -175.0(4) . . . . ? C4 C5 C6 C7 175.6(4) . . . . ? C1 C5 C6 C7 1.5(5) . . . . ? C11 C6 C7 C8 -0.4(6) . . . . ? C5 C6 C7 C8 -177.4(4) . . . . ? C11 C6 C7 P1 174.5(3) . . . . ? C5 C6 C7 P1 -2.4(4) . . . . ? C1 P1 C7 C8 176.9(4) . . . . ? C12 P1 C7 C8 -74.6(4) . . . . ? Se1 P1 C7 C8 53.4(4) . . . . ? C1 P1 C7 C6 2.1(3) . . . . ? C12 P1 C7 C6 110.6(3) . . . . ? Se1 P1 C7 C6 -121.4(3) . . . . ? C6 C7 C8 C9 -0.3(6) . . . . ? P1 C7 C8 C9 -174.6(3) . . . . ? C7 C8 C9 C10 0.4(6) . . . . ? C8 C9 C10 C11 0.3(7) . . . . ? C7 C6 C11 C10 1.1(6) . . . . ? C5 C6 C11 C10 177.5(4) . . . . ? C9 C10 C11 C6 -1.1(6) . . . . ? C1 P1 C12 C13 -134.6(4) . . . . ? C7 P1 C12 C13 128.6(4) . . . . ? Se1 P1 C12 C13 0.7(5) . . . . ? C1 P1 C12 C17 43.4(4) . . . . ? C7 P1 C12 C17 -53.4(4) . . . . ? Se1 P1 C12 C17 178.7(3) . . . . ? C17 C12 C13 C14 0.8(7) . . . . ? P1 C12 C13 C14 178.9(4) . . . . ? C12 C13 C14 C15 1.4(8) . . . . ? C13 C14 C15 C16 -2.3(7) . . . . ? C14 C15 C16 C17 1.1(7) . . . . ? C15 C16 C17 C12 1.2(7) . . . . ? C13 C12 C17 C16 -2.1(7) . . . . ? P1 C12 C17 C16 179.8(4) . . . . ? C1 C2 C18 C19 -19.0(6) . . . . ? C3 C2 C18 C19 159.4(4) . . . . ? C1 C2 C18 C23 161.9(4) . . . . ? C3 C2 C18 C23 -19.7(5) . . . . ? C23 C18 C19 C20 0.8(6) . . . . ? C2 C18 C19 C20 -178.3(4) . . . . ? C18 C19 C20 C21 -0.3(6) . . . . ? C19 C20 C21 C22 -0.5(6) . . . . ? C20 C21 C22 C23 0.8(6) . . . . ? C21 C22 C23 C18 -0.2(6) . . . . ? C19 C18 C23 C22 -0.6(6) . . . . ? C2 C18 C23 C22 178.6(3) . . . . ? C2 C3 C24 C29 114.1(5) . . . . ? C4 C3 C24 C29 -127.8(4) . . . . ? C2 C3 C24 C25 -64.1(5) . . . . ? C4 C3 C24 C25 54.0(5) . . . . ? C29 C24 C25 C26 -0.3(7) . . . . ? C3 C24 C25 C26 177.9(4) . . . . ? C24 C25 C26 C27 -0.3(7) . . . . ? C25 C26 C27 C28 -0.3(7) . . . . ? C26 C27 C28 C29 1.5(7) . . . . ? C25 C24 C29 C28 1.5(7) . . . . ? C3 C24 C29 C28 -176.6(4) . . . . ? C27 C28 C29 C24 -2.1(7) . . . . ? C5 C4 C30 C31 -136.3(5) . . . . ? C3 C4 C30 C31 49.5(6) . . . . ? C5 C4 C30 C35 46.0(6) . . . . ? C3 C4 C30 C35 -128.2(4) . . . . ? C35 C30 C31 C32 -0.9(6) . . . . ? C4 C30 C31 C32 -178.7(4) . . . . ? C30 C31 C32 C33 0.3(7) . . . . ? C31 C32 C33 C34 0.5(7) . . . . ? C32 C33 C34 C35 -0.7(7) . . . . ? C33 C34 C35 C30 0.2(7) . . . . ? C31 C30 C35 C34 0.6(6) . . . . ? C4 C30 C35 C34 178.4(4) . . . . ? _diffrn_measured_fraction_theta_max 0.730 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.930 _refine_diff_density_max 0.578 _refine_diff_density_min -0.561 _refine_diff_density_rms 0.090 # Attachment '9.cif' data_9 _database_code_depnum_ccdc_archive 'CCDC 614297' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C38 H28' _chemical_formula_sum 'C38 H28' _chemical_formula_weight 484.38 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0030 0.0020 '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 9.7367(18) _cell_length_b 10.2143(17) _cell_length_c 14.483(2) _cell_angle_alpha 91.593(10) _cell_angle_beta 91.994(11) _cell_angle_gamma 114.825(8) _cell_volume 1305.1(4) _cell_formula_units_Z 2 _cell_measurement_temperature 93(2) _cell_measurement_reflns_used 3710 _cell_measurement_theta_min 2.1984 _cell_measurement_theta_max 28.0773 _exptl_crystal_description Prism _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.233 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 512 _exptl_absorpt_coefficient_mu 0.070 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9896 _exptl_absorpt_correction_T_max 0.9972 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 93(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator confocal _diffrn_measurement_device_type CCD _diffrn_measurement_method dtprofit.ref _diffrn_detector_area_resol_mean 0.83 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8008 _diffrn_reflns_av_R_equivalents 0.0350 _diffrn_reflns_av_sigmaI/netI 0.0439 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.31 _diffrn_reflns_theta_max 27.33 _reflns_number_total 4377 _reflns_number_gt 3217 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Corp., 2004)' _computing_cell_refinement 'CrystalClear (Rigaku Corp., 2004)' _computing_data_reduction 'CrystalClear (Rigaku Corp., 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics PLATON _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0324P)^2^+2.7316P] 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 4377 _refine_ls_number_parameters 343 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1042 _refine_ls_R_factor_gt 0.0699 _refine_ls_wR_factor_ref 0.1631 _refine_ls_wR_factor_gt 0.1437 _refine_ls_goodness_of_fit_ref 1.158 _refine_ls_restrained_S_all 1.158 _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 C1 C 0.5829(4) 0.2623(3) 0.0989(2) 0.0180(7) Uani 1 1 d . . . C36 C 0.2285(4) 0.1090(4) -0.4807(2) 0.0292(8) Uani 1 1 d . . . H36 H 0.1867 0.0229 -0.5189 0.035 Uiso 1 1 calc R . . C13 C 0.5244(4) 0.1709(4) 0.2609(2) 0.0203(7) Uani 1 1 d . . . H13 H 0.4266 0.1039 0.2382 0.024 Uiso 1 1 calc R . . C3 C 0.8135(4) 0.2272(4) 0.0552(2) 0.0204(7) Uani 1 1 d . . . H3 H 0.8006 0.1696 0.1074 0.025 Uiso 1 1 calc R . . C9 C 0.7658(4) 0.3619(4) 0.2372(2) 0.0196(7) Uani 1 1 d . . . H9 H 0.8353 0.4275 0.1977 0.024 Uiso 1 1 calc R . . C23 C 0.3288(4) 0.3454(4) 0.1840(2) 0.0219(7) Uani 1 1 d . . . H23 H 0.4185 0.4328 0.1860 0.026 Uiso 1 1 calc R . . C26 C 0.0675(4) 0.0905(4) 0.1815(3) 0.0309(9) Uani 1 1 d . . . H26 H -0.0210 0.0023 0.1814 0.037 Uiso 1 1 calc R . . C35 C 0.2503(4) 0.1016(4) -0.3857(2) 0.0240(8) Uani 1 1 d . . . H35 H 0.2236 0.0103 -0.3597 0.029 Uiso 1 1 calc R . . C38 C 0.3274(4) 0.3664(4) -0.4639(2) 0.0265(8) Uani 1 1 d . . . H38 H 0.3545 0.4574 -0.4904 0.032 Uiso 1 1 calc R . . C15 C 0.9029(4) 0.2784(4) 0.5112(2) 0.0243(8) Uani 1 1 d . . . H15 H 0.9748 0.2977 0.4649 0.029 Uiso 1 1 calc R . . C24 C 0.2103(4) 0.3344(4) 0.2381(2) 0.0269(8) Uani 1 1 d . . . H24 H 0.2186 0.4152 0.2760 0.032 Uiso 1 1 calc R . . C8 C 0.6228(3) 0.2654(3) 0.2004(2) 0.0178(7) Uani 1 1 d . . . C27 C 0.1844(4) 0.1025(4) 0.1251(2) 0.0238(8) Uani 1 1 d . . . H27 H 0.1739 0.0233 0.0850 0.029 Uiso 1 1 calc R . . C32 C 0.3853(4) 0.1232(4) -0.1899(2) 0.0196(7) Uani 1 1 d . . . H32 H 0.3973 0.0536 -0.2297 0.024 Uiso 1 1 calc R . . C37 C 0.2677(4) 0.2418(4) -0.5197(2) 0.0288(9) Uani 1 1 d . . . H37 H 0.2535 0.2467 -0.5846 0.035 Uiso 1 1 calc R . . C25 C 0.0802(4) 0.2073(4) 0.2378(2) 0.0308(9) Uani 1 1 d . . . H25 H 0.0000 0.2001 0.2758 0.037 Uiso 1 1 calc R . . C34 C 0.3105(4) 0.2258(4) -0.3290(2) 0.0202(7) Uani 1 1 d . . . C22 C 0.3173(4) 0.2298(4) 0.1268(2) 0.0200(7) Uani 1 1 d . . . C19 C 0.6570(4) 0.2442(4) 0.5578(2) 0.0270(8) Uani 1 1 d . . . H19 H 0.5579 0.2364 0.5433 0.032 Uiso 1 1 calc R . . C33 C 0.4188(3) 0.1267(4) -0.0954(2) 0.0188(7) Uani 1 1 d . . . H33 H 0.4563 0.0614 -0.0719 0.023 Uiso 1 1 calc R . . C2 C 0.7112(3) 0.2881(4) 0.0367(2) 0.0186(7) Uani 1 1 d . . . C11 C 0.7097(4) 0.2688(4) 0.3894(2) 0.0195(7) Uani 1 1 d . . . C10 C 0.8084(4) 0.3641(4) 0.3296(2) 0.0203(7) Uani 1 1 d . . . H10 H 0.9060 0.4314 0.3525 0.024 Uiso 1 1 calc R . . C30 C 0.3091(4) 0.3151(4) -0.1662(2) 0.0198(7) Uani 1 1 d . . . H30 H 0.2724 0.3811 -0.1896 0.024 Uiso 1 1 calc R . . C7 C 0.7361(4) 0.3747(3) -0.0391(2) 0.0190(7) Uani 1 1 d . . . H7 H 0.6698 0.4191 -0.0526 0.023 Uiso 1 1 calc R . . C6 C 0.8561(4) 0.3976(4) -0.0954(2) 0.0218(7) Uani 1 1 d . . . H6 H 0.8713 0.4571 -0.1468 0.026 Uiso 1 1 calc R . . C5 C 0.9540(4) 0.3329(4) -0.0761(2) 0.0220(7) Uani 1 1 d . . . H5 H 1.0351 0.3469 -0.1151 0.026 Uiso 1 1 calc R . . C4 C 0.9330(4) 0.2488(4) -0.0007(2) 0.0223(7) Uani 1 1 d . . . H4 H 1.0003 0.2057 0.0130 0.027 Uiso 1 1 calc R . . C28 C 0.3983(3) 0.2244(4) -0.0349(2) 0.0187(7) Uani 1 1 d . . . C29 C 0.3367(4) 0.3142(4) -0.0717(2) 0.0203(7) Uani 1 1 d . . . H29 H 0.3133 0.3759 -0.0312 0.024 Uiso 1 1 calc R . . C31 C 0.3343(3) 0.2208(4) -0.2271(2) 0.0193(7) Uani 1 1 d . . . C12 C 0.5667(4) 0.1730(4) 0.3537(2) 0.0207(7) Uani 1 1 d . . . H12 H 0.4971 0.1080 0.3935 0.025 Uiso 1 1 calc R . . C17 C 0.8421(4) 0.2417(4) 0.6706(2) 0.0292(8) Uani 1 1 d . . . H17 H 0.8701 0.2315 0.7326 0.035 Uiso 1 1 calc R . . C39 C 0.3483(4) 0.3595(4) -0.3689(2) 0.0234(8) Uani 1 1 d . . . H39 H 0.3883 0.4458 -0.3309 0.028 Uiso 1 1 calc R . . C14 C 0.7573(4) 0.2651(4) 0.4876(2) 0.0204(7) Uani 1 1 d . . . C18 C 0.7000(4) 0.2345(4) 0.6488(2) 0.0303(9) Uani 1 1 d . . . H18 H 0.6314 0.2230 0.6962 0.036 Uiso 1 1 calc R . . C21 C 0.4424(4) 0.2390(4) 0.0659(2) 0.0201(7) Uani 1 1 d . . . C16 C 0.9435(4) 0.2638(4) 0.6018(2) 0.0280(8) Uani 1 1 d . . . H16 H 1.0415 0.2689 0.6167 0.034 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 0.0232(17) 0.0151(17) 0.0171(16) 0.0007(13) 0.0022(13) 0.0093(13) C36 0.029(2) 0.035(2) 0.0235(18) -0.0050(16) -0.0031(15) 0.0142(17) C13 0.0141(16) 0.0238(18) 0.0238(17) -0.0002(14) -0.0005(13) 0.0091(14) C3 0.0172(16) 0.0220(18) 0.0200(16) 0.0001(14) -0.0017(13) 0.0065(14) C9 0.0186(17) 0.0215(18) 0.0200(16) 0.0065(14) 0.0057(13) 0.0090(14) C23 0.0220(17) 0.0260(19) 0.0192(17) 0.0043(15) -0.0010(13) 0.0115(15) C26 0.0169(18) 0.040(2) 0.034(2) 0.0104(18) 0.0035(15) 0.0097(16) C35 0.0254(19) 0.025(2) 0.0219(17) 0.0028(15) 0.0009(14) 0.0112(15) C38 0.0240(18) 0.031(2) 0.0267(18) 0.0126(16) 0.0050(15) 0.0132(16) C15 0.0211(18) 0.029(2) 0.0228(17) 0.0008(15) 0.0029(14) 0.0106(15) C24 0.035(2) 0.041(2) 0.0152(16) 0.0039(15) 0.0032(14) 0.0259(18) C8 0.0178(16) 0.0203(18) 0.0180(16) 0.0020(14) 0.0026(13) 0.0105(14) C27 0.0208(18) 0.0255(19) 0.0247(18) 0.0031(15) 0.0001(14) 0.0091(15) C32 0.0182(17) 0.0192(18) 0.0202(16) -0.0009(14) 0.0024(13) 0.0067(14) C37 0.028(2) 0.048(2) 0.0164(17) 0.0065(17) 0.0004(14) 0.0208(18) C25 0.025(2) 0.052(3) 0.0253(18) 0.0110(18) 0.0088(15) 0.0244(19) C34 0.0149(16) 0.029(2) 0.0208(16) 0.0023(15) 0.0012(13) 0.0126(14) C22 0.0188(17) 0.028(2) 0.0160(16) 0.0028(14) -0.0011(13) 0.0123(15) C19 0.0193(18) 0.039(2) 0.0247(18) 0.0038(16) 0.0009(14) 0.0138(16) C33 0.0160(16) 0.0200(18) 0.0213(16) 0.0052(14) 0.0018(13) 0.0082(13) C2 0.0158(16) 0.0198(18) 0.0179(16) -0.0017(14) -0.0018(13) 0.0056(13) C11 0.0228(17) 0.0228(19) 0.0186(16) 0.0012(14) 0.0019(13) 0.0150(14) C10 0.0174(16) 0.0238(19) 0.0204(16) 0.0001(14) -0.0023(13) 0.0098(14) C30 0.0161(16) 0.0249(19) 0.0215(17) 0.0027(14) 0.0024(13) 0.0114(14) C7 0.0196(17) 0.0175(17) 0.0186(16) -0.0028(14) -0.0007(13) 0.0068(14) C6 0.0225(18) 0.0244(19) 0.0168(16) 0.0026(14) 0.0016(13) 0.0082(14) C5 0.0158(16) 0.0268(19) 0.0203(16) -0.0017(14) 0.0033(13) 0.0058(14) C4 0.0185(17) 0.0227(19) 0.0263(18) -0.0035(15) -0.0002(14) 0.0096(14) C28 0.0136(16) 0.0217(18) 0.0191(16) 0.0016(14) 0.0012(13) 0.0058(13) C29 0.0168(16) 0.0226(18) 0.0224(17) -0.0011(14) 0.0029(13) 0.0092(14) C31 0.0102(16) 0.0229(18) 0.0226(17) 0.0031(14) 0.0019(13) 0.0045(13) C12 0.0180(17) 0.0262(19) 0.0220(17) 0.0072(14) 0.0064(13) 0.0126(14) C17 0.033(2) 0.035(2) 0.0155(16) -0.0009(16) -0.0052(15) 0.0110(17) C39 0.0212(18) 0.028(2) 0.0228(17) 0.0021(15) 0.0012(14) 0.0124(15) C14 0.0212(17) 0.0188(18) 0.0217(17) -0.0003(14) 0.0012(13) 0.0089(14) C18 0.0257(19) 0.043(2) 0.0210(17) 0.0020(16) 0.0045(15) 0.0132(17) C21 0.0216(17) 0.0194(18) 0.0215(17) 0.0040(14) 0.0031(14) 0.0105(14) C16 0.0223(18) 0.033(2) 0.0285(19) -0.0032(16) -0.0033(15) 0.0123(16) _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 C21 1.353(4) . ? C1 C2 1.502(4) . ? C1 C8 1.503(4) . ? C36 C37 1.388(5) . ? C36 C35 1.394(5) . ? C36 H36 0.9500 . ? C13 C12 1.389(5) . ? C13 C8 1.395(5) . ? C13 H13 0.9500 . ? C3 C4 1.384(5) . ? C3 C2 1.401(5) . ? C3 H3 0.9500 . ? C9 C10 1.384(4) . ? C9 C8 1.400(4) . ? C9 H9 0.9500 . ? C23 C24 1.385(5) . ? C23 C22 1.386(5) . ? C23 H23 0.9500 . ? C26 C25 1.385(5) . ? C26 C27 1.389(5) . ? C26 H26 0.9500 . ? C35 C34 1.383(5) . ? C35 H35 0.9500 . ? C38 C37 1.378(5) . ? C38 C39 1.392(5) . ? C38 H38 0.9500 . ? C15 C16 1.388(5) . ? C15 C14 1.395(5) . ? C15 H15 0.9500 . ? C24 C25 1.382(5) . ? C24 H24 0.9500 . ? C27 C22 1.396(5) . ? C27 H27 0.9500 . ? C32 C33 1.392(4) . ? C32 C31 1.400(5) . ? C32 H32 0.9500 . ? C37 H37 0.9500 . ? C25 H25 0.9500 . ? C34 C39 1.404(5) . ? C34 C31 1.491(5) . ? C22 C21 1.501(4) . ? C19 C18 1.386(5) . ? C19 C14 1.393(5) . ? C19 H19 0.9500 . ? C33 C28 1.391(5) . ? C33 H33 0.9500 . ? C2 C7 1.393(5) . ? C11 C10 1.393(5) . ? C11 C12 1.393(5) . ? C11 C14 1.487(5) . ? C10 H10 0.9500 . ? C30 C29 1.387(5) . ? C30 C31 1.390(4) . ? C30 H30 0.9500 . ? C7 C6 1.389(4) . ? C7 H7 0.9500 . ? C6 C5 1.394(5) . ? C6 H6 0.9500 . ? C5 C4 1.376(5) . ? C5 H5 0.9500 . ? C4 H4 0.9500 . ? C28 C29 1.397(5) . ? C28 C21 1.492(4) . ? C29 H29 0.9500 . ? C12 H12 0.9500 . ? C17 C18 1.379(5) . ? C17 C16 1.383(5) . ? C17 H17 0.9500 . ? C39 H39 0.9500 . ? C18 H18 0.9500 . ? C16 H16 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 C21 C1 C2 122.4(3) . . ? C21 C1 C8 122.6(3) . . ? C2 C1 C8 114.9(3) . . ? C37 C36 C35 120.3(3) . . ? C37 C36 H36 119.9 . . ? C35 C36 H36 119.9 . . ? C12 C13 C8 121.3(3) . . ? C12 C13 H13 119.3 . . ? C8 C13 H13 119.3 . . ? C4 C3 C2 121.6(3) . . ? C4 C3 H3 119.2 . . ? C2 C3 H3 119.2 . . ? C10 C9 C8 121.7(3) . . ? C10 C9 H9 119.1 . . ? C8 C9 H9 119.1 . . ? C24 C23 C22 120.4(3) . . ? C24 C23 H23 119.8 . . ? C22 C23 H23 119.8 . . ? C25 C26 C27 119.9(4) . . ? C25 C26 H26 120.0 . . ? C27 C26 H26 120.0 . . ? C34 C35 C36 120.7(3) . . ? C34 C35 H35 119.7 . . ? C36 C35 H35 119.7 . . ? C37 C38 C39 120.3(3) . . ? C37 C38 H38 119.8 . . ? C39 C38 H38 119.8 . . ? C16 C15 C14 120.5(3) . . ? C16 C15 H15 119.8 . . ? C14 C15 H15 119.8 . . ? C25 C24 C23 120.7(3) . . ? C25 C24 H24 119.7 . . ? C23 C24 H24 119.7 . . ? C13 C8 C9 117.1(3) . . ? C13 C8 C1 122.7(3) . . ? C9 C8 C1 120.1(3) . . ? C26 C27 C22 120.7(3) . . ? C26 C27 H27 119.7 . . ? C22 C27 H27 119.7 . . ? C33 C32 C31 120.9(3) . . ? C33 C32 H32 119.5 . . ? C31 C32 H32 119.5 . . ? C38 C37 C36 119.6(3) . . ? C38 C37 H37 120.2 . . ? C36 C37 H37 120.2 . . ? C24 C25 C26 119.5(3) . . ? C24 C25 H25 120.3 . . ? C26 C25 H25 120.3 . . ? C35 C34 C39 118.6(3) . . ? C35 C34 C31 121.7(3) . . ? C39 C34 C31 119.6(3) . . ? C23 C22 C27 118.7(3) . . ? C23 C22 C21 121.8(3) . . ? C27 C22 C21 119.5(3) . . ? C18 C19 C14 120.8(3) . . ? C18 C19 H19 119.6 . . ? C14 C19 H19 119.6 . . ? C32 C33 C28 121.0(3) . . ? C32 C33 H33 119.5 . . ? C28 C33 H33 119.5 . . ? C7 C2 C3 117.4(3) . . ? C7 C2 C1 122.4(3) . . ? C3 C2 C1 120.2(3) . . ? C10 C11 C12 118.1(3) . . ? C10 C11 C14 121.1(3) . . ? C12 C11 C14 120.8(3) . . ? C9 C10 C11 120.7(3) . . ? C9 C10 H10 119.6 . . ? C11 C10 H10 119.6 . . ? C29 C30 C31 120.9(3) . . ? C29 C30 H30 119.6 . . ? C31 C30 H30 119.6 . . ? C6 C7 C2 121.3(3) . . ? C6 C7 H7 119.4 . . ? C2 C7 H7 119.4 . . ? C7 C6 C5 119.8(3) . . ? C7 C6 H6 120.1 . . ? C5 C6 H6 120.1 . . ? C4 C5 C6 119.9(3) . . ? C4 C5 H5 120.1 . . ? C6 C5 H5 120.1 . . ? C5 C4 C3 119.9(3) . . ? C5 C4 H4 120.0 . . ? C3 C4 H4 120.0 . . ? C33 C28 C29 117.7(3) . . ? C33 C28 C21 122.9(3) . . ? C29 C28 C21 119.4(3) . . ? C30 C29 C28 121.3(3) . . ? C30 C29 H29 119.3 . . ? C28 C29 H29 119.3 . . ? C30 C31 C32 117.9(3) . . ? C30 C31 C34 120.9(3) . . ? C32 C31 C34 121.2(3) . . ? C13 C12 C11 121.0(3) . . ? C13 C12 H12 119.5 . . ? C11 C12 H12 119.5 . . ? C18 C17 C16 119.6(3) . . ? C18 C17 H17 120.2 . . ? C16 C17 H17 120.2 . . ? C38 C39 C34 120.4(3) . . ? C38 C39 H39 119.8 . . ? C34 C39 H39 119.8 . . ? C19 C14 C15 118.4(3) . . ? C19 C14 C11 121.1(3) . . ? C15 C14 C11 120.5(3) . . ? C17 C18 C19 120.3(3) . . ? C17 C18 H18 119.9 . . ? C19 C18 H18 119.9 . . ? C1 C21 C28 123.1(3) . . ? C1 C21 C22 123.4(3) . . ? C28 C21 C22 113.5(3) . . ? C17 C16 C15 120.4(3) . . ? C17 C16 H16 119.8 . . ? C15 C16 H16 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 C37 C36 C35 C34 0.3(5) . . . . ? C22 C23 C24 C25 1.4(5) . . . . ? C12 C13 C8 C9 0.1(5) . . . . ? C12 C13 C8 C1 177.6(3) . . . . ? C10 C9 C8 C13 0.0(5) . . . . ? C10 C9 C8 C1 -177.6(3) . . . . ? C21 C1 C8 C13 39.0(5) . . . . ? C2 C1 C8 C13 -141.4(3) . . . . ? C21 C1 C8 C9 -143.6(3) . . . . ? C2 C1 C8 C9 36.0(4) . . . . ? C25 C26 C27 C22 2.2(5) . . . . ? C39 C38 C37 C36 -0.1(5) . . . . ? C35 C36 C37 C38 -0.5(5) . . . . ? C23 C24 C25 C26 -1.0(5) . . . . ? C27 C26 C25 C24 -0.8(5) . . . . ? C36 C35 C34 C39 0.4(5) . . . . ? C36 C35 C34 C31 179.7(3) . . . . ? C24 C23 C22 C27 -0.1(5) . . . . ? C24 C23 C22 C21 178.8(3) . . . . ? C26 C27 C22 C23 -1.7(5) . . . . ? C26 C27 C22 C21 179.4(3) . . . . ? C31 C32 C33 C28 1.9(5) . . . . ? C4 C3 C2 C7 -1.6(5) . . . . ? C4 C3 C2 C1 -180.0(3) . . . . ? C21 C1 C2 C7 41.2(5) . . . . ? C8 C1 C2 C7 -138.4(3) . . . . ? C21 C1 C2 C3 -140.5(3) . . . . ? C8 C1 C2 C3 39.9(4) . . . . ? C8 C9 C10 C11 0.4(5) . . . . ? C12 C11 C10 C9 -0.9(5) . . . . ? C14 C11 C10 C9 176.7(3) . . . . ? C3 C2 C7 C6 1.3(5) . . . . ? C1 C2 C7 C6 179.6(3) . . . . ? C2 C7 C6 C5 0.0(5) . . . . ? C7 C6 C5 C4 -1.1(5) . . . . ? C6 C5 C4 C3 0.8(5) . . . . ? C2 C3 C4 C5 0.5(5) . . . . ? C32 C33 C28 C29 2.8(5) . . . . ? C32 C33 C28 C21 -175.8(3) . . . . ? C31 C30 C29 C28 3.5(5) . . . . ? C33 C28 C29 C30 -5.5(5) . . . . ? C21 C28 C29 C30 173.1(3) . . . . ? C29 C30 C31 C32 1.3(5) . . . . ? C29 C30 C31 C34 -177.5(3) . . . . ? C33 C32 C31 C30 -4.0(5) . . . . ? C33 C32 C31 C34 174.8(3) . . . . ? C35 C34 C31 C30 -142.5(3) . . . . ? C39 C34 C31 C30 36.7(4) . . . . ? C35 C34 C31 C32 38.7(5) . . . . ? C39 C34 C31 C32 -142.0(3) . . . . ? C8 C13 C12 C11 -0.6(5) . . . . ? C10 C11 C12 C13 0.9(5) . . . . ? C14 C11 C12 C13 -176.7(3) . . . . ? C37 C38 C39 C34 0.8(5) . . . . ? C35 C34 C39 C38 -0.9(5) . . . . ? C31 C34 C39 C38 179.8(3) . . . . ? C18 C19 C14 C15 -1.0(6) . . . . ? C18 C19 C14 C11 177.2(3) . . . . ? C16 C15 C14 C19 3.2(5) . . . . ? C16 C15 C14 C11 -175.0(3) . . . . ? C10 C11 C14 C19 141.9(3) . . . . ? C12 C11 C14 C19 -40.5(5) . . . . ? C10 C11 C14 C15 -39.9(5) . . . . ? C12 C11 C14 C15 137.6(3) . . . . ? C16 C17 C18 C19 2.3(6) . . . . ? C14 C19 C18 C17 -1.8(6) . . . . ? C2 C1 C21 C28 5.3(5) . . . . ? C8 C1 C21 C28 -175.1(3) . . . . ? C2 C1 C21 C22 -172.8(3) . . . . ? C8 C1 C21 C22 6.8(5) . . . . ? C33 C28 C21 C1 53.6(5) . . . . ? C29 C28 C21 C1 -125.0(4) . . . . ? C33 C28 C21 C22 -128.2(3) . . . . ? C29 C28 C21 C22 53.3(4) . . . . ? C23 C22 C21 C1 62.2(5) . . . . ? C27 C22 C21 C1 -118.9(4) . . . . ? C23 C22 C21 C28 -116.0(3) . . . . ? C27 C22 C21 C28 62.8(4) . . . . ? C18 C17 C16 C15 -0.1(6) . . . . ? C14 C15 C16 C17 -2.7(6) . . . . ? _diffrn_measured_fraction_theta_max 0.743 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.901 _refine_diff_density_max 0.258 _refine_diff_density_min -0.268 _refine_diff_density_rms 0.060 # Attachment '16.cif' data_16 _database_code_depnum_ccdc_archive 'CCDC 614298' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C30 H22' _chemical_formula_sum 'C30 H22' _chemical_formula_weight 382.48 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 5.872(3) _cell_length_b 7.437(3) _cell_length_c 11.851(7) _cell_angle_alpha 83.77(3) _cell_angle_beta 89.75(3) _cell_angle_gamma 81.48(2) _cell_volume 508.8(4) _cell_formula_units_Z 1 _cell_measurement_temperature 93(2) _cell_measurement_reflns_used 1472 _cell_measurement_theta_min 2.7858 _cell_measurement_theta_max 27.9444 _exptl_crystal_description Prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.248 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 202 _exptl_absorpt_coefficient_mu 0.071 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9930 _exptl_absorpt_correction_T_max 0.9979 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 93(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator confocal _diffrn_measurement_device_type CCD _diffrn_measurement_method dtprofit.ref _diffrn_detector_area_resol_mean 0.83 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3376 _diffrn_reflns_av_R_equivalents 0.0834 _diffrn_reflns_av_sigmaI/netI 0.0798 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.73 _diffrn_reflns_theta_max 28.00 _reflns_number_total 1840 _reflns_number_gt 1357 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Corp., 2004)' _computing_cell_refinement 'CrystalClear (Rigaku Corp., 2004)' _computing_data_reduction 'CrystalClear (Rigaku Corp., 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics PLATON _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0957P)^2^+0.4080P] 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 1840 _refine_ls_number_parameters 137 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1009 _refine_ls_R_factor_gt 0.0788 _refine_ls_wR_factor_ref 0.2176 _refine_ls_wR_factor_gt 0.1955 _refine_ls_goodness_of_fit_ref 1.071 _refine_ls_restrained_S_all 1.071 _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 C4 C 1.0094(5) 0.1142(4) 0.2579(2) 0.0263(7) Uani 1 1 d . . . C1 C 0.8409(5) 0.1369(4) 0.4477(2) 0.0248(6) Uani 1 1 d . . . H1 H 0.7301 0.2307 0.4109 0.030 Uiso 1 1 calc R . . C2 C 1.0109(5) 0.0490(4) 0.3822(2) 0.0244(6) Uani 1 1 d . . . C5 C 0.8240(5) 0.0959(4) 0.1889(2) 0.0281(7) Uani 1 1 d . . . H5 H 0.7016 0.0375 0.2208 0.034 Uiso 1 1 calc R . . C6 C 0.8150(5) 0.1616(4) 0.0744(3) 0.0336(7) Uani 1 1 d . . . H6 H 0.6894 0.1461 0.0279 0.040 Uiso 1 1 calc R . . C3 C 0.8247(5) 0.0937(4) 0.5658(2) 0.0247(6) Uani 1 1 d . . . C15 C 0.6812(5) 0.2588(4) 0.7328(2) 0.0278(7) Uani 1 1 d . . . H15 H 0.8292 0.2249 0.7673 0.033 Uiso 1 1 calc R . . C11 C 0.4203(5) 0.2547(4) 0.5796(2) 0.0278(7) Uani 1 1 d . . . H11 H 0.3869 0.2172 0.5082 0.033 Uiso 1 1 calc R . . C12 C 0.2489(5) 0.3625(4) 0.6347(3) 0.0299(7) Uani 1 1 d . . . H12 H 0.1012 0.3990 0.6002 0.036 Uiso 1 1 calc R . . C13 C 0.2944(5) 0.4161(4) 0.7395(3) 0.0307(7) Uani 1 1 d . . . H13 H 0.1771 0.4877 0.7776 0.037 Uiso 1 1 calc R . . C7 C 0.9931(6) 0.2507(4) 0.0285(3) 0.0344(8) Uani 1 1 d . . . H7 H 0.9878 0.2975 -0.0495 0.041 Uiso 1 1 calc R . . C14 C 0.5099(5) 0.3653(4) 0.7886(2) 0.0305(7) Uani 1 1 d . . . H14 H 0.5418 0.4028 0.8602 0.037 Uiso 1 1 calc R . . C9 C 1.1866(5) 0.2042(4) 0.2101(3) 0.0298(7) Uani 1 1 d . . . H9 H 1.3133 0.2194 0.2559 0.036 Uiso 1 1 calc R . . C10 C 0.6405(5) 0.2009(4) 0.6277(2) 0.0250(6) Uani 1 1 d . . . C8 C 1.1767(5) 0.2712(4) 0.0956(3) 0.0319(7) Uani 1 1 d . . . H8 H 1.2973 0.3315 0.0636 0.038 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 C4 0.0293(15) 0.0245(14) 0.0229(14) -0.0035(10) 0.0034(11) 0.0042(12) C1 0.0246(14) 0.0238(14) 0.0257(15) -0.0030(10) 0.0016(11) -0.0025(12) C2 0.0269(14) 0.0268(14) 0.0205(14) -0.0042(10) 0.0005(11) -0.0062(12) C5 0.0273(14) 0.0288(15) 0.0283(15) -0.0061(11) 0.0027(11) -0.0029(13) C6 0.0350(16) 0.0380(17) 0.0265(16) -0.0046(12) -0.0008(12) -0.0007(14) C3 0.0243(14) 0.0266(14) 0.0234(14) -0.0034(10) 0.0025(11) -0.0034(12) C15 0.0269(14) 0.0286(15) 0.0278(15) -0.0062(11) 0.0025(11) -0.0018(13) C11 0.0302(15) 0.0280(15) 0.0260(15) -0.0034(11) 0.0039(11) -0.0064(13) C12 0.0249(15) 0.0283(15) 0.0355(17) -0.0010(12) 0.0032(12) -0.0027(13) C13 0.0320(16) 0.0253(15) 0.0337(17) -0.0030(11) 0.0089(12) -0.0008(13) C7 0.0449(18) 0.0313(16) 0.0247(15) -0.0021(12) 0.0077(13) 0.0005(14) C14 0.0371(17) 0.0283(15) 0.0264(15) -0.0073(11) 0.0052(12) -0.0028(13) C9 0.0279(15) 0.0287(15) 0.0320(16) -0.0042(11) 0.0042(12) -0.0015(13) C10 0.0267(14) 0.0235(14) 0.0252(15) -0.0029(10) 0.0034(11) -0.0048(12) C8 0.0326(16) 0.0305(16) 0.0320(17) -0.0031(12) 0.0108(13) -0.0035(14) _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 C4 C5 1.396(4) . ? C4 C9 1.404(4) . ? C4 C2 1.500(4) . ? C1 C2 1.391(4) . ? C1 C3 1.407(4) . ? C1 H1 0.9500 . ? C2 C3 1.413(4) 2_756 ? C5 C6 1.390(4) . ? C5 H5 0.9500 . ? C6 C7 1.397(5) . ? C6 H6 0.9500 . ? C3 C2 1.413(4) 2_756 ? C3 C10 1.486(4) . ? C15 C10 1.394(4) . ? C15 C14 1.395(4) . ? C15 H15 0.9500 . ? C11 C12 1.397(4) . ? C11 C10 1.400(4) . ? C11 H11 0.9500 . ? C12 C13 1.384(4) . ? C12 H12 0.9500 . ? C13 C14 1.378(4) . ? C13 H13 0.9500 . ? C7 C8 1.379(5) . ? C7 H7 0.9500 . ? C14 H14 0.9500 . ? C9 C8 1.392(4) . ? C9 H9 0.9500 . ? C8 H8 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 C5 C4 C9 118.7(3) . . ? C5 C4 C2 120.3(3) . . ? C9 C4 C2 120.9(3) . . ? C2 C1 C3 123.3(3) . . ? C2 C1 H1 118.4 . . ? C3 C1 H1 118.4 . . ? C1 C2 C3 119.7(2) . 2_756 ? C1 C2 C4 117.0(2) . . ? C3 C2 C4 123.3(2) 2_756 . ? C6 C5 C4 121.2(3) . . ? C6 C5 H5 119.4 . . ? C4 C5 H5 119.4 . . ? C5 C6 C7 119.1(3) . . ? C5 C6 H6 120.4 . . ? C7 C6 H6 120.4 . . ? C1 C3 C2 117.0(2) . 2_756 ? C1 C3 C10 118.6(2) . . ? C2 C3 C10 124.4(2) 2_756 . ? C10 C15 C14 121.7(3) . . ? C10 C15 H15 119.2 . . ? C14 C15 H15 119.2 . . ? C12 C11 C10 121.2(3) . . ? C12 C11 H11 119.4 . . ? C10 C11 H11 119.4 . . ? C13 C12 C11 120.0(3) . . ? C13 C12 H12 120.0 . . ? C11 C12 H12 120.0 . . ? C14 C13 C12 119.9(3) . . ? C14 C13 H13 120.0 . . ? C12 C13 H13 120.0 . . ? C8 C7 C6 120.4(3) . . ? C8 C7 H7 119.8 . . ? C6 C7 H7 119.8 . . ? C13 C14 C15 119.9(3) . . ? C13 C14 H14 120.0 . . ? C15 C14 H14 120.0 . . ? C8 C9 C4 120.0(3) . . ? C8 C9 H9 120.0 . . ? C4 C9 H9 120.0 . . ? C15 C10 C11 117.3(3) . . ? C15 C10 C3 121.9(3) . . ? C11 C10 C3 120.7(2) . . ? C7 C8 C9 120.5(3) . . ? C7 C8 H8 119.7 . . ? C9 C8 H8 119.7 . . ? 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 C3 C1 C2 C3 1.3(4) . . . 2_756 ? C3 C1 C2 C4 -178.2(3) . . . . ? C5 C4 C2 C1 -64.0(4) . . . . ? C9 C4 C2 C1 112.1(3) . . . . ? C5 C4 C2 C3 116.4(3) . . . 2_756 ? C9 C4 C2 C3 -67.4(4) . . . 2_756 ? C9 C4 C5 C6 1.3(4) . . . . ? C2 C4 C5 C6 177.5(3) . . . . ? C4 C5 C6 C7 -1.3(4) . . . . ? C2 C1 C3 C2 -1.3(4) . . . 2_756 ? C2 C1 C3 C10 178.0(2) . . . . ? C10 C11 C12 C13 -0.9(4) . . . . ? C11 C12 C13 C14 1.0(4) . . . . ? C5 C6 C7 C8 0.8(4) . . . . ? C12 C13 C14 C15 -0.5(4) . . . . ? C10 C15 C14 C13 -0.2(5) . . . . ? C5 C4 C9 C8 -0.8(4) . . . . ? C2 C4 C9 C8 -177.0(3) . . . . ? C14 C15 C10 C11 0.3(4) . . . . ? C14 C15 C10 C3 177.5(3) . . . . ? C12 C11 C10 C15 0.2(4) . . . . ? C12 C11 C10 C3 -177.0(2) . . . . ? C1 C3 C10 C15 -138.3(3) . . . . ? C2 C3 C10 C15 40.9(4) 2_756 . . . ? C1 C3 C10 C11 38.8(4) . . . . ? C2 C3 C10 C11 -142.0(3) 2_756 . . . ? C6 C7 C8 C9 -0.3(4) . . . . ? C4 C9 C8 C7 0.3(4) . . . . ? _diffrn_measured_fraction_theta_max 0.746 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.918 _refine_diff_density_max 0.318 _refine_diff_density_min -0.271 _refine_diff_density_rms 0.075 data_1 _database_code_depnum_ccdc_archive 'CCDC 633293' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H20' _chemical_formula_sum 'C26 H20' _chemical_formula_weight 332.42 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 P2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 9.786(3) _cell_length_b 9.186(3) _cell_length_c 10.804(3) _cell_angle_alpha 90.00 _cell_angle_beta 108.007(8) _cell_angle_gamma 90.00 _cell_volume 923.7(5) _cell_formula_units_Z 2 _cell_measurement_temperature 93(2) _cell_measurement_reflns_used 3600 _cell_measurement_theta_min 3.1147 _cell_measurement_theta_max 25.3491 _exptl_crystal_description Prism _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.1500 _exptl_crystal_size_mid 0.1500 _exptl_crystal_size_min 0.1000 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.195 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 352 _exptl_absorpt_coefficient_mu 0.067 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8453 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 93(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator confocal _diffrn_measurement_device_type CCD _diffrn_measurement_method dtprofit.ref _diffrn_detector_area_resol_mean 0.83 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5717 _diffrn_reflns_av_R_equivalents 0.0233 _diffrn_reflns_av_sigmaI/netI 0.0339 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.12 _diffrn_reflns_theta_max 25.34 _reflns_number_total 2932 _reflns_number_gt 2805 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Corp., 2004)' _computing_cell_refinement 'CrystalClear (Rigaku Corp., 2004)' _computing_data_reduction 'CrystalClear (Rigaku Corp., 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0542P)^2^+0.0846P] 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 -3(8) _refine_ls_number_reflns 2932 _refine_ls_number_parameters 236 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0357 _refine_ls_R_factor_gt 0.0341 _refine_ls_wR_factor_ref 0.0886 _refine_ls_wR_factor_gt 0.0871 _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_restrained_S_all 1.051 _refine_ls_shift/su_max 0.016 _refine_ls_shift/su_mean 0.002 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 0.52861(16) 0.08358(19) 0.04892(15) 0.0189(4) Uani 1 1 d . . . C2 C 0.39292(17) 0.1469(2) 0.00012(16) 0.0216(4) Uani 1 1 d . . . H2A H 0.3499 0.1901 0.0588 0.026 Uiso 1 1 calc R . . C3 C 0.31954(19) 0.1480(2) -0.13193(16) 0.0289(4) Uani 1 1 d . . . H3A H 0.2281 0.1934 -0.1630 0.035 Uiso 1 1 calc R . . C4 C 0.3789(2) 0.0835(2) -0.21807(17) 0.0345(5) Uani 1 1 d . . . H4A H 0.3279 0.0826 -0.3085 0.041 Uiso 1 1 calc R . . C5 C 0.5132(2) 0.0197(2) -0.17246(16) 0.0322(5) Uani 1 1 d . . . H5A H 0.5547 -0.0243 -0.2320 0.039 Uiso 1 1 calc R . . C6 C 0.58781(19) 0.0196(2) -0.04037(16) 0.0247(4) Uani 1 1 d . . . H6A H 0.6801 -0.0243 -0.0102 0.030 Uiso 1 1 calc R . . C7 C 0.50313(16) 0.04751(18) 0.27148(14) 0.0166(4) Uani 1 1 d . . . C8 C 0.48887(17) 0.14408(19) 0.36634(15) 0.0201(4) Uani 1 1 d . . . H8A H 0.5400 0.2336 0.3797 0.024 Uiso 1 1 calc R . . C9 C 0.40074(17) 0.1109(2) 0.44144(16) 0.0232(4) Uani 1 1 d . . . H9A H 0.3917 0.1777 0.5056 0.028 Uiso 1 1 calc R . . C10 C 0.32584(18) -0.0196(2) 0.42290(16) 0.0252(4) Uani 1 1 d . . . H10A H 0.2669 -0.0431 0.4753 0.030 Uiso 1 1 calc R . . C11 C 0.33735(17) -0.1158(2) 0.32733(16) 0.0240(4) Uani 1 1 d . . . H11A H 0.2857 -0.2050 0.3141 0.029 Uiso 1 1 calc R . . C12 C 0.42418(17) -0.08174(19) 0.25113(15) 0.0194(4) Uani 1 1 d . . . H12A H 0.4299 -0.1469 0.1846 0.023 Uiso 1 1 calc R . . C13 C 0.83853(16) 0.16791(18) 0.17938(14) 0.0175(3) Uani 1 1 d . . . C14 C 0.79679(18) 0.2831(2) 0.09129(15) 0.0206(4) Uani 1 1 d . . . H14A H 0.7035 0.3238 0.0737 0.025 Uiso 1 1 calc R . . C15 C 0.89005(19) 0.3385(2) 0.02929(16) 0.0250(4) Uani 1 1 d . . . H15A H 0.8597 0.4160 -0.0312 0.030 Uiso 1 1 calc R . . C16 C 1.02705(18) 0.2821(2) 0.05469(16) 0.0247(4) Uani 1 1 d . . . H16A H 1.0904 0.3203 0.0116 0.030 Uiso 1 1 calc R . . C17 C 1.07120(17) 0.1694(2) 0.14348(15) 0.0212(4) Uani 1 1 d . . . H17A H 1.1654 0.1307 0.1620 0.025 Uiso 1 1 calc R . . C18 C 0.97790(17) 0.1133(2) 0.20535(15) 0.0201(4) Uani 1 1 d . . . H18A H 1.0092 0.0364 0.2664 0.024 Uiso 1 1 calc R . . C19 C 0.81007(16) 0.09135(19) 0.39425(15) 0.0186(4) Uani 1 1 d . . . C20 C 0.89771(17) 0.2010(2) 0.46675(16) 0.0218(4) Uani 1 1 d . . . H20A H 0.9157 0.2858 0.4240 0.026 Uiso 1 1 calc R . . C21 C 0.95909(18) 0.1875(2) 0.60090(17) 0.0261(4) Uani 1 1 d . . . H21A H 1.0179 0.2633 0.6491 0.031 Uiso 1 1 calc R . . C22 C 0.93451(18) 0.0636(2) 0.66436(16) 0.0277(4) Uani 1 1 d . . . H22A H 0.9751 0.0550 0.7561 0.033 Uiso 1 1 calc R . . C23 C 0.85072(18) -0.0469(2) 0.59349(17) 0.0265(4) Uani 1 1 d . . . H23A H 0.8346 -0.1323 0.6365 0.032 Uiso 1 1 calc R . . C24 C 0.78982(17) -0.0342(2) 0.45966(16) 0.0222(4) Uani 1 1 d . . . H24A H 0.7336 -0.1118 0.4119 0.027 Uiso 1 1 calc R . . C25 C 0.60070(16) 0.08155(18) 0.19234(15) 0.0174(3) Uani 1 1 d . . . C26 C 0.74192(16) 0.11020(18) 0.25076(15) 0.0175(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0220(8) 0.0159(9) 0.0195(8) -0.0007(7) 0.0076(7) -0.0065(7) C2 0.0212(8) 0.0248(10) 0.0190(8) 0.0001(7) 0.0067(6) -0.0044(7) C3 0.0260(9) 0.0357(12) 0.0207(8) 0.0062(8) 0.0011(7) -0.0083(8) C4 0.0427(11) 0.0402(13) 0.0163(9) 0.0001(9) 0.0028(8) -0.0167(10) C5 0.0502(12) 0.0309(12) 0.0219(10) -0.0098(8) 0.0205(9) -0.0166(9) C6 0.0292(9) 0.0205(10) 0.0280(10) -0.0051(8) 0.0142(8) -0.0065(8) C7 0.0152(7) 0.0196(9) 0.0134(8) 0.0015(7) 0.0018(6) 0.0016(6) C8 0.0186(8) 0.0212(9) 0.0182(8) 0.0014(7) 0.0024(6) 0.0021(7) C9 0.0256(9) 0.0278(10) 0.0176(8) 0.0011(7) 0.0087(6) 0.0031(7) C10 0.0227(8) 0.0338(11) 0.0216(8) 0.0062(8) 0.0106(7) 0.0008(8) C11 0.0194(8) 0.0252(10) 0.0256(9) 0.0055(8) 0.0046(7) -0.0032(7) C12 0.0190(8) 0.0204(9) 0.0173(8) 0.0000(7) 0.0035(6) -0.0002(7) C13 0.0188(8) 0.0169(9) 0.0176(8) -0.0033(7) 0.0066(6) -0.0025(7) C14 0.0194(8) 0.0202(9) 0.0213(8) 0.0013(7) 0.0049(7) -0.0004(7) C15 0.0278(9) 0.0242(10) 0.0218(9) 0.0050(8) 0.0062(7) -0.0028(7) C16 0.0258(9) 0.0286(10) 0.0231(9) -0.0036(8) 0.0123(7) -0.0081(8) C17 0.0170(8) 0.0242(10) 0.0234(8) -0.0071(8) 0.0077(6) -0.0015(7) C18 0.0202(8) 0.0194(9) 0.0206(8) 0.0002(7) 0.0060(6) 0.0001(7) C19 0.0143(7) 0.0198(9) 0.0225(8) 0.0033(7) 0.0068(6) 0.0028(7) C20 0.0190(8) 0.0233(10) 0.0234(9) 0.0019(7) 0.0070(7) 0.0010(7) C21 0.0198(8) 0.0303(11) 0.0259(9) -0.0037(8) 0.0038(7) 0.0012(7) C22 0.0218(9) 0.0395(12) 0.0190(9) 0.0061(8) 0.0020(7) 0.0089(8) C23 0.0225(8) 0.0304(11) 0.0264(9) 0.0135(8) 0.0073(7) 0.0072(8) C24 0.0190(8) 0.0200(9) 0.0260(9) 0.0061(8) 0.0048(7) 0.0012(7) C25 0.0208(8) 0.0128(8) 0.0198(8) 0.0006(7) 0.0079(6) 0.0011(7) C26 0.0189(8) 0.0148(9) 0.0198(8) 0.0029(7) 0.0072(6) 0.0030(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.395(2) . ? C1 C6 1.399(2) . ? C1 C25 1.491(2) . ? C2 C3 1.385(2) . ? C2 H2A 0.9500 . ? C3 C4 1.375(3) . ? C3 H3A 0.9500 . ? C4 C5 1.383(3) . ? C4 H4A 0.9500 . ? C5 C6 1.388(2) . ? C5 H5A 0.9500 . ? C6 H6A 0.9500 . ? C7 C8 1.395(2) . ? C7 C12 1.396(2) . ? C7 C25 1.498(2) . ? C8 C9 1.388(2) . ? C8 H8A 0.9500 . ? C9 C10 1.387(3) . ? C9 H9A 0.9500 . ? C10 C11 1.390(3) . ? C10 H10A 0.9500 . ? C11 C12 1.389(2) . ? C11 H11A 0.9500 . ? C12 H12A 0.9500 . ? C13 C14 1.397(2) . ? C13 C18 1.398(2) . ? C13 C26 1.490(2) . ? C14 C15 1.385(2) . ? C14 H14A 0.9500 . ? C15 C16 1.383(3) . ? C15 H15A 0.9500 . ? C16 C17 1.386(3) . ? C16 H16A 0.9500 . ? C17 C18 1.387(2) . ? C17 H17A 0.9500 . ? C18 H18A 0.9500 . ? C19 C20 1.396(2) . ? C19 C24 1.398(2) . ? C19 C26 1.496(2) . ? C20 C21 1.392(2) . ? C20 H20A 0.9500 . ? C21 C22 1.387(3) . ? C21 H21A 0.9500 . ? C22 C23 1.379(3) . ? C22 H22A 0.9500 . ? C23 C24 1.388(2) . ? C23 H23A 0.9500 . ? C24 H24A 0.9500 . ? C25 C26 1.356(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C6 117.59(14) . . ? C2 C1 C25 119.16(14) . . ? C6 C1 C25 123.21(14) . . ? C3 C2 C1 121.49(16) . . ? C3 C2 H2A 119.3 . . ? C1 C2 H2A 119.3 . . ? C4 C3 C2 120.07(17) . . ? C4 C3 H3A 120.0 . . ? C2 C3 H3A 120.0 . . ? C3 C4 C5 119.70(16) . . ? C3 C4 H4A 120.1 . . ? C5 C4 H4A 120.1 . . ? C4 C5 C6 120.43(16) . . ? C4 C5 H5A 119.8 . . ? C6 C5 H5A 119.8 . . ? C5 C6 C1 120.71(17) . . ? C5 C6 H6A 119.6 . . ? C1 C6 H6A 119.6 . . ? C8 C7 C12 118.70(15) . . ? C8 C7 C25 120.85(15) . . ? C12 C7 C25 120.45(14) . . ? C9 C8 C7 120.76(16) . . ? C9 C8 H8A 119.6 . . ? C7 C8 H8A 119.6 . . ? C10 C9 C8 120.07(16) . . ? C10 C9 H9A 120.0 . . ? C8 C9 H9A 120.0 . . ? C9 C10 C11 119.76(15) . . ? C9 C10 H10A 120.1 . . ? C11 C10 H10A 120.1 . . ? C12 C11 C10 120.13(17) . . ? C12 C11 H11A 119.9 . . ? C10 C11 H11A 119.9 . . ? C11 C12 C7 120.54(16) . . ? C11 C12 H12A 119.7 . . ? C7 C12 H12A 119.7 . . ? C14 C13 C18 118.05(14) . . ? C14 C13 C26 121.56(14) . . ? C18 C13 C26 120.28(15) . . ? C15 C14 C13 120.68(15) . . ? C15 C14 H14A 119.7 . . ? C13 C14 H14A 119.7 . . ? C16 C15 C14 120.61(17) . . ? C16 C15 H15A 119.7 . . ? C14 C15 H15A 119.7 . . ? C15 C16 C17 119.52(16) . . ? C15 C16 H16A 120.2 . . ? C17 C16 H16A 120.2 . . ? C16 C17 C18 120.02(16) . . ? C16 C17 H17A 120.0 . . ? C18 C17 H17A 120.0 . . ? C17 C18 C13 121.11(16) . . ? C17 C18 H18A 119.4 . . ? C13 C18 H18A 119.4 . . ? C20 C19 C24 118.02(14) . . ? C20 C19 C26 119.86(15) . . ? C24 C19 C26 122.12(15) . . ? C21 C20 C19 120.86(16) . . ? C21 C20 H20A 119.6 . . ? C19 C20 H20A 119.6 . . ? C22 C21 C20 120.15(17) . . ? C22 C21 H21A 119.9 . . ? C20 C21 H21A 119.9 . . ? C23 C22 C21 119.59(16) . . ? C23 C22 H22A 120.2 . . ? C21 C22 H22A 120.2 . . ? C22 C23 C24 120.43(17) . . ? C22 C23 H23A 119.8 . . ? C24 C23 H23A 119.8 . . ? C23 C24 C19 120.90(16) . . ? C23 C24 H24A 119.5 . . ? C19 C24 H24A 119.5 . . ? C26 C25 C1 124.62(13) . . ? C26 C25 C7 120.83(14) . . ? C1 C25 C7 114.54(13) . . ? C25 C26 C13 123.13(14) . . ? C25 C26 C19 121.58(14) . . ? C13 C26 C19 115.25(13) . . ? 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 -0.6(3) . . . . ? C25 C1 C2 C3 -178.17(16) . . . . ? C1 C2 C3 C4 1.2(3) . . . . ? C2 C3 C4 C5 -1.1(3) . . . . ? C3 C4 C5 C6 0.5(3) . . . . ? C4 C5 C6 C1 0.1(3) . . . . ? C2 C1 C6 C5 0.0(2) . . . . ? C25 C1 C6 C5 177.38(15) . . . . ? C12 C7 C8 C9 1.6(2) . . . . ? C25 C7 C8 C9 -178.63(14) . . . . ? C7 C8 C9 C10 0.2(2) . . . . ? C8 C9 C10 C11 -1.2(2) . . . . ? C9 C10 C11 C12 0.4(2) . . . . ? C10 C11 C12 C7 1.4(2) . . . . ? C8 C7 C12 C11 -2.4(2) . . . . ? C25 C7 C12 C11 177.84(15) . . . . ? C18 C13 C14 C15 1.6(2) . . . . ? C26 C13 C14 C15 177.73(15) . . . . ? C13 C14 C15 C16 -0.8(3) . . . . ? C14 C15 C16 C17 -0.3(3) . . . . ? C15 C16 C17 C18 0.5(3) . . . . ? C16 C17 C18 C13 0.3(2) . . . . ? C14 C13 C18 C17 -1.4(2) . . . . ? C26 C13 C18 C17 -177.54(15) . . . . ? C24 C19 C20 C21 -2.1(2) . . . . ? C26 C19 C20 C21 178.24(14) . . . . ? C19 C20 C21 C22 0.5(2) . . . . ? C20 C21 C22 C23 1.0(3) . . . . ? C21 C22 C23 C24 -0.7(3) . . . . ? C22 C23 C24 C19 -1.0(2) . . . . ? C20 C19 C24 C23 2.4(2) . . . . ? C26 C19 C24 C23 -177.98(14) . . . . ? C2 C1 C25 C26 -137.80(18) . . . . ? C6 C1 C25 C26 44.8(2) . . . . ? C2 C1 C25 C7 41.0(2) . . . . ? C6 C1 C25 C7 -136.40(17) . . . . ? C8 C7 C25 C26 56.3(2) . . . . ? C12 C7 C25 C26 -123.94(17) . . . . ? C8 C7 C25 C1 -122.54(16) . . . . ? C12 C7 C25 C1 57.2(2) . . . . ? C1 C25 C26 C13 9.0(3) . . . . ? C7 C25 C26 C13 -169.76(15) . . . . ? C1 C25 C26 C19 -173.67(15) . . . . ? C7 C25 C26 C19 7.6(2) . . . . ? C14 C13 C26 C25 45.8(2) . . . . ? C18 C13 C26 C25 -138.20(17) . . . . ? C14 C13 C26 C19 -131.73(16) . . . . ? C18 C13 C26 C19 44.3(2) . . . . ? C20 C19 C26 C25 -132.77(18) . . . . ? C24 C19 C26 C25 47.6(2) . . . . ? C20 C19 C26 C13 44.8(2) . . . . ? C24 C19 C26 C13 -134.82(16) . . . . ? _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 25.34 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 0.158 _refine_diff_density_min -0.156 _refine_diff_density_rms 0.035 # Attachment '2.cif' data_p21n _database_code_depnum_ccdc_archive 'CCDC 633294' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C30 H28 O4' _chemical_formula_sum 'C30 H28 O4' _chemical_formula_weight 452.52 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/n loop_ _symmetry_equiv_pos_as_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 9.5954(12) _cell_length_b 15.3661(19) _cell_length_c 16.1322(19) _cell_angle_alpha 90.00 _cell_angle_beta 93.312(3) _cell_angle_gamma 90.00 _cell_volume 2374.6(5) _cell_formula_units_Z 4 _cell_measurement_temperature 93(2) _cell_measurement_reflns_used 9114 _cell_measurement_theta_min 1.83 _cell_measurement_theta_max 28.35 _exptl_crystal_description Prism _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.266 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 960 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9755 _exptl_absorpt_correction_T_max 0.9755 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 93(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator confocal _diffrn_measurement_device_type CCD _diffrn_measurement_method dtprofit.ref _diffrn_detector_area_resol_mean 0.83 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12943 _diffrn_reflns_av_R_equivalents 0.0724 _diffrn_reflns_av_sigmaI/netI 0.0476 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.65 _diffrn_reflns_theta_max 27.26 _reflns_number_total 4207 _reflns_number_gt 3531 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Corp., 2004)' _computing_cell_refinement 'CrystalClear (Rigaku Corp., 2004)' _computing_data_reduction 'CrystalClear (Rigaku Corp., 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics PLATON _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0545P)^2^+1.0636P] 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 4207 _refine_ls_number_parameters 311 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0653 _refine_ls_R_factor_gt 0.0517 _refine_ls_wR_factor_ref 0.1262 _refine_ls_wR_factor_gt 0.1188 _refine_ls_goodness_of_fit_ref 1.076 _refine_ls_restrained_S_all 1.076 _refine_ls_shift/su_max 0.010 _refine_ls_shift/su_mean 0.001 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 O32 O 1.45622(14) 0.07044(8) 0.24591(7) 0.0254(3) Uani 1 1 d . . . O5 O 1.44161(14) 0.41351(9) 0.92108(8) 0.0283(3) Uani 1 1 d . . . O12 O 1.93457(14) 0.43208(9) 0.42157(8) 0.0305(3) Uani 1 1 d . . . O25 O 0.98095(14) 0.08535(9) 0.75507(9) 0.0331(4) Uani 1 1 d . . . C21 C 1.40188(18) 0.22678(12) 0.56131(10) 0.0193(4) Uani 1 1 d . . . C22 C 1.29009(19) 0.18791(11) 0.61057(11) 0.0202(4) Uani 1 1 d . . . C29 C 1.41181(18) 0.19030(12) 0.47576(11) 0.0200(4) Uani 1 1 d . . . C1 C 1.49008(18) 0.28873(12) 0.59371(11) 0.0191(4) Uani 1 1 d . . . C14 C 1.71077(19) 0.26972(12) 0.51696(11) 0.0206(4) Uani 1 1 d . . . H14 H 1.7034 0.2086 0.5241 0.025 Uiso 1 1 calc R . . C10 C 1.62646(19) 0.41357(12) 0.53950(11) 0.0225(4) Uani 1 1 d . . . H10 H 1.5619 0.4520 0.5629 0.027 Uiso 1 1 calc R . . C33 C 1.44059(18) 0.20408(12) 0.32730(11) 0.0207(4) Uani 1 1 d . . . H33 H 1.4503 0.2402 0.2802 0.025 Uiso 1 1 calc R . . C12 C 1.83206(19) 0.39206(12) 0.46341(10) 0.0226(4) Uani 1 1 d . . . C27 C 1.15260(19) 0.18439(12) 0.57875(11) 0.0222(4) Uani 1 1 d . . . H27 H 1.1306 0.2053 0.5241 0.027 Uiso 1 1 calc R . . C6 C 1.57101(19) 0.35008(12) 0.81838(11) 0.0214(4) Uani 1 1 d . . . H6 H 1.6470 0.3452 0.8586 0.026 Uiso 1 1 calc R . . C31 C 1.42554(18) 0.06214(12) 0.38823(11) 0.0209(4) Uani 1 1 d . . . H31 H 1.4256 0.0006 0.3829 0.025 Uiso 1 1 calc R . . C25 C 1.0771(2) 0.11931(12) 0.70411(12) 0.0246(4) Uani 1 1 d . . . C11 C 1.7343(2) 0.44736(12) 0.49636(11) 0.0250(4) Uani 1 1 d . . . H11 H 1.7418 0.5085 0.4891 0.030 Uiso 1 1 calc R . . C4 C 1.33528(19) 0.39504(12) 0.78077(11) 0.0223(4) Uani 1 1 d . . . H4 H 1.2498 0.4207 0.7950 0.027 Uiso 1 1 calc R . . C35 C 1.4689(2) 0.12182(13) 0.17256(11) 0.0253(4) Uani 1 1 d . . . H35A H 1.3808 0.1523 0.1590 0.038 Uiso 1 1 calc R . . H35B H 1.4906 0.0838 0.1262 0.038 Uiso 1 1 calc R . . H35C H 1.5440 0.1645 0.1823 0.038 Uiso 1 1 calc R . . C23 C 1.3191(2) 0.15338(13) 0.69008(11) 0.0245(4) Uani 1 1 d . . . H23 H 1.4127 0.1532 0.7128 0.029 Uiso 1 1 calc R . . C32 C 1.44108(18) 0.11408(12) 0.31863(11) 0.0204(4) Uani 1 1 d . . . C30 C 1.41000(18) 0.09967(12) 0.46494(11) 0.0193(4) Uani 1 1 d . . . H30 H 1.3978 0.0632 0.5115 0.023 Uiso 1 1 calc R . . C13 C 1.82140(19) 0.30272(12) 0.47445(11) 0.0223(4) Uani 1 1 d . . . H13 H 1.8887 0.2646 0.4533 0.027 Uiso 1 1 calc R . . C34 C 1.42589(18) 0.24133(12) 0.40506(11) 0.0202(4) Uani 1 1 d . . . H34 H 1.4254 0.3029 0.4101 0.024 Uiso 1 1 calc R . . C7 C 1.58412(19) 0.32089(12) 0.73842(11) 0.0214(4) Uani 1 1 d . . . H7 H 1.6704 0.2964 0.7240 0.026 Uiso 1 1 calc R . . C5 C 1.44501(19) 0.38687(12) 0.83976(11) 0.0206(4) Uani 1 1 d . . . C2 C 1.47430(18) 0.32629(11) 0.67795(11) 0.0191(4) Uani 1 1 d . . . C24 C 1.2146(2) 0.11945(13) 0.73627(11) 0.0262(4) Uani 1 1 d . . . H24 H 1.2369 0.0962 0.7900 0.031 Uiso 1 1 calc R . . C9 C 1.61052(18) 0.32366(12) 0.54933(10) 0.0192(4) Uani 1 1 d . . . C26 C 1.04595(19) 0.15116(12) 0.62444(12) 0.0244(4) Uani 1 1 d . . . H26 H 0.9526 0.1502 0.6014 0.029 Uiso 1 1 calc R . . C8 C 1.3163(2) 0.45401(13) 0.94514(12) 0.0282(5) Uani 1 1 d . . . H8A H 1.2949 0.5042 0.9092 0.042 Uiso 1 1 calc R . . H8B H 1.3287 0.4734 1.0030 0.042 Uiso 1 1 calc R . . H8C H 1.2392 0.4122 0.9398 0.042 Uiso 1 1 calc R . . C15 C 2.0439(2) 0.37881(15) 0.39331(13) 0.0350(5) Uani 1 1 d . . . H15A H 2.0950 0.3520 0.4411 0.053 Uiso 1 1 calc R . . H15B H 2.1079 0.4146 0.3626 0.053 Uiso 1 1 calc R . . H15C H 2.0039 0.3331 0.3568 0.053 Uiso 1 1 calc R . . C3 C 1.35113(19) 0.36540(12) 0.70047(11) 0.0224(4) Uani 1 1 d . . . H3 H 1.2761 0.3720 0.6599 0.027 Uiso 1 1 calc R . . C28 C 0.8434(2) 0.07148(15) 0.72028(15) 0.0394(6) Uani 1 1 d . . . H28A H 0.7995 0.1277 0.7067 0.059 Uiso 1 1 calc R . . H28B H 0.7885 0.0407 0.7605 0.059 Uiso 1 1 calc R . . H28C H 0.8471 0.0365 0.6697 0.059 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 O32 0.0351(7) 0.0242(7) 0.0169(6) -0.0024(5) 0.0030(5) -0.0006(6) O5 0.0304(7) 0.0330(8) 0.0216(7) -0.0062(6) 0.0027(6) 0.0069(6) O12 0.0330(8) 0.0313(8) 0.0284(7) 0.0028(6) 0.0115(6) -0.0064(6) O25 0.0347(8) 0.0298(8) 0.0366(8) -0.0048(6) 0.0167(7) -0.0084(6) C21 0.0196(9) 0.0194(9) 0.0187(9) 0.0017(7) -0.0007(7) 0.0011(7) C22 0.0245(9) 0.0168(9) 0.0194(9) -0.0029(7) 0.0009(7) -0.0015(8) C29 0.0165(9) 0.0235(10) 0.0196(9) 0.0011(8) -0.0018(7) -0.0010(7) C1 0.0192(9) 0.0178(9) 0.0201(9) 0.0003(7) -0.0003(7) 0.0026(7) C14 0.0244(9) 0.0162(9) 0.0211(9) -0.0028(7) -0.0010(8) -0.0018(8) C10 0.0237(9) 0.0204(10) 0.0232(9) -0.0017(8) 0.0000(8) 0.0014(8) C33 0.0215(9) 0.0216(10) 0.0187(9) 0.0048(8) -0.0008(7) -0.0032(8) C12 0.0232(9) 0.0284(11) 0.0158(8) 0.0010(8) -0.0008(7) -0.0059(8) C27 0.0263(10) 0.0174(9) 0.0227(9) -0.0003(8) 0.0002(8) 0.0012(8) C6 0.0200(9) 0.0220(10) 0.0218(9) -0.0006(8) -0.0021(7) -0.0005(8) C31 0.0229(9) 0.0166(9) 0.0230(9) 0.0007(7) -0.0008(8) -0.0001(7) C25 0.0304(11) 0.0173(10) 0.0275(10) -0.0082(8) 0.0130(8) -0.0036(8) C11 0.0305(11) 0.0189(10) 0.0251(9) 0.0027(8) -0.0009(8) -0.0017(8) C4 0.0178(9) 0.0209(10) 0.0284(10) -0.0026(8) 0.0050(8) 0.0018(8) C35 0.0250(10) 0.0338(11) 0.0171(9) 0.0016(8) 0.0030(8) 0.0028(9) C23 0.0254(10) 0.0272(11) 0.0203(9) -0.0031(8) -0.0032(8) -0.0068(8) C32 0.0181(9) 0.0245(10) 0.0183(9) -0.0023(8) -0.0005(7) -0.0015(8) C30 0.0194(9) 0.0201(10) 0.0182(9) 0.0047(7) -0.0006(7) -0.0019(7) C13 0.0219(9) 0.0242(10) 0.0209(9) -0.0036(8) 0.0007(7) 0.0013(8) C34 0.0215(9) 0.0161(9) 0.0226(9) 0.0000(7) -0.0002(7) -0.0030(7) C7 0.0185(9) 0.0215(10) 0.0246(9) -0.0020(8) 0.0031(7) -0.0001(7) C5 0.0252(10) 0.0163(9) 0.0206(9) -0.0018(7) 0.0040(7) -0.0021(8) C2 0.0199(9) 0.0164(9) 0.0211(9) 0.0001(7) 0.0024(7) -0.0032(7) C24 0.0363(11) 0.0265(11) 0.0158(9) -0.0020(8) 0.0024(8) -0.0078(9) C9 0.0197(9) 0.0220(10) 0.0155(8) -0.0006(7) -0.0029(7) -0.0021(7) C26 0.0201(9) 0.0204(10) 0.0327(10) -0.0044(8) 0.0021(8) -0.0011(8) C8 0.0334(11) 0.0256(11) 0.0266(10) 0.0009(8) 0.0106(9) 0.0060(9) C15 0.0332(11) 0.0392(13) 0.0340(11) 0.0019(10) 0.0130(9) -0.0034(10) C3 0.0186(9) 0.0234(10) 0.0247(9) -0.0003(8) -0.0026(8) -0.0014(8) C28 0.0297(11) 0.0322(12) 0.0583(15) -0.0044(11) 0.0185(10) -0.0051(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 O32 C32 1.366(2) . ? O32 C35 1.434(2) . ? O5 C5 1.376(2) . ? O5 C8 1.428(2) . ? O12 C12 1.370(2) . ? O12 C15 1.426(2) . ? O25 C25 1.374(2) . ? O25 C28 1.420(3) . ? C21 C1 1.358(3) . ? C21 C22 1.496(2) . ? C21 C29 1.498(2) . ? C22 C27 1.389(3) . ? C22 C23 1.401(3) . ? C29 C34 1.397(2) . ? C29 C30 1.404(3) . ? C1 C2 1.492(2) . ? C1 C9 1.494(2) . ? C14 C13 1.392(3) . ? C14 C9 1.394(3) . ? C14 H14 0.9500 . ? C10 C11 1.381(3) . ? C10 C9 1.400(3) . ? C10 H10 0.9500 . ? C33 C32 1.390(3) . ? C33 C34 1.393(3) . ? C33 H33 0.9500 . ? C12 C13 1.389(3) . ? C12 C11 1.394(3) . ? C27 C26 1.392(3) . ? C27 H27 0.9500 . ? C6 C7 1.378(3) . ? C6 C5 1.396(3) . ? C6 H6 0.9500 . ? C31 C30 1.381(3) . ? C31 C32 1.393(3) . ? C31 H31 0.9500 . ? C25 C24 1.389(3) . ? C25 C26 1.392(3) . ? C11 H11 0.9500 . ? C4 C5 1.384(3) . ? C4 C3 1.390(3) . ? C4 H4 0.9500 . ? C35 H35A 0.9800 . ? C35 H35B 0.9800 . ? C35 H35C 0.9800 . ? C23 C24 1.386(3) . ? C23 H23 0.9500 . ? C30 H30 0.9500 . ? C13 H13 0.9500 . ? C34 H34 0.9500 . ? C7 C2 1.397(3) . ? C7 H7 0.9500 . ? C2 C3 1.393(3) . ? C24 H24 0.9500 . ? C26 H26 0.9500 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C3 H3 0.9500 . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 H28C 0.9800 . ? 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 C32 O32 C35 117.19(14) . . ? C5 O5 C8 117.10(14) . . ? C12 O12 C15 117.52(15) . . ? C25 O25 C28 117.49(16) . . ? C1 C21 C22 121.70(16) . . ? C1 C21 C29 123.06(16) . . ? C22 C21 C29 115.20(15) . . ? C27 C22 C23 117.27(17) . . ? C27 C22 C21 120.95(16) . . ? C23 C22 C21 121.78(16) . . ? C34 C29 C30 117.16(16) . . ? C34 C29 C21 123.82(16) . . ? C30 C29 C21 119.01(15) . . ? C21 C1 C2 121.86(16) . . ? C21 C1 C9 123.33(16) . . ? C2 C1 C9 114.80(15) . . ? C13 C14 C9 122.02(17) . . ? C13 C14 H14 119.0 . . ? C9 C14 H14 119.0 . . ? C11 C10 C9 121.20(17) . . ? C11 C10 H10 119.4 . . ? C9 C10 H10 119.4 . . ? C32 C33 C34 120.03(16) . . ? C32 C33 H33 120.0 . . ? C34 C33 H33 120.0 . . ? O12 C12 C13 124.54(17) . . ? O12 C12 C11 115.62(17) . . ? C13 C12 C11 119.83(17) . . ? C22 C27 C26 122.02(17) . . ? C22 C27 H27 119.0 . . ? C26 C27 H27 119.0 . . ? C7 C6 C5 119.36(17) . . ? C7 C6 H6 120.3 . . ? C5 C6 H6 120.3 . . ? C30 C31 C32 120.35(17) . . ? C30 C31 H31 119.8 . . ? C32 C31 H31 119.8 . . ? O25 C25 C24 115.67(17) . . ? O25 C25 C26 124.79(18) . . ? C24 C25 C26 119.54(17) . . ? C10 C11 C12 120.22(17) . . ? C10 C11 H11 119.9 . . ? C12 C11 H11 119.9 . . ? C5 C4 C3 119.44(16) . . ? C5 C4 H4 120.3 . . ? C3 C4 H4 120.3 . . ? O32 C35 H35A 109.5 . . ? O32 C35 H35B 109.5 . . ? H35A C35 H35B 109.5 . . ? O32 C35 H35C 109.5 . . ? H35A C35 H35C 109.5 . . ? H35B C35 H35C 109.5 . . ? C24 C23 C22 121.52(17) . . ? C24 C23 H23 119.2 . . ? C22 C23 H23 119.2 . . ? O32 C32 C33 125.16(16) . . ? O32 C32 C31 115.64(16) . . ? C33 C32 C31 119.20(16) . . ? C31 C30 C29 121.63(16) . . ? C31 C30 H30 119.2 . . ? C29 C30 H30 119.2 . . ? C12 C13 C14 119.15(17) . . ? C12 C13 H13 120.4 . . ? C14 C13 H13 120.4 . . ? C33 C34 C29 121.60(17) . . ? C33 C34 H34 119.2 . . ? C29 C34 H34 119.2 . . ? C6 C7 C2 121.89(17) . . ? C6 C7 H7 119.1 . . ? C2 C7 H7 119.1 . . ? O5 C5 C4 124.73(16) . . ? O5 C5 C6 115.12(16) . . ? C4 C5 C6 120.15(16) . . ? C3 C2 C7 117.45(16) . . ? C3 C2 C1 122.47(16) . . ? C7 C2 C1 120.06(16) . . ? C23 C24 C25 120.08(17) . . ? C23 C24 H24 120.0 . . ? C25 C24 H24 120.0 . . ? C14 C9 C10 117.52(17) . . ? C14 C9 C1 122.38(16) . . ? C10 C9 C1 120.10(16) . . ? C25 C26 C27 119.52(17) . . ? C25 C26 H26 120.2 . . ? C27 C26 H26 120.2 . . ? O5 C8 H8A 109.5 . . ? O5 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? O5 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? O12 C15 H15A 109.5 . . ? O12 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? O12 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C4 C3 C2 121.66(17) . . ? C4 C3 H3 119.2 . . ? C2 C3 H3 119.2 . . ? O25 C28 H28A 109.5 . . ? O25 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? O25 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 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 C1 C21 C22 C27 128.77(19) . . . . ? C29 C21 C22 C27 -53.2(2) . . . . ? C1 C21 C22 C23 -51.5(3) . . . . ? C29 C21 C22 C23 126.52(18) . . . . ? C1 C21 C29 C34 -47.5(3) . . . . ? C22 C21 C29 C34 134.51(18) . . . . ? C1 C21 C29 C30 131.09(19) . . . . ? C22 C21 C29 C30 -46.9(2) . . . . ? C22 C21 C1 C2 -4.5(3) . . . . ? C29 C21 C1 C2 177.62(16) . . . . ? C22 C21 C1 C9 174.59(16) . . . . ? C29 C21 C1 C9 -3.3(3) . . . . ? C15 O12 C12 C13 -5.3(3) . . . . ? C15 O12 C12 C11 174.48(16) . . . . ? C23 C22 C27 C26 2.4(3) . . . . ? C21 C22 C27 C26 -177.84(16) . . . . ? C28 O25 C25 C24 -170.49(17) . . . . ? C28 O25 C25 C26 8.5(3) . . . . ? C9 C10 C11 C12 -1.7(3) . . . . ? O12 C12 C11 C10 179.84(16) . . . . ? C13 C12 C11 C10 -0.4(3) . . . . ? C27 C22 C23 C24 -1.9(3) . . . . ? C21 C22 C23 C24 178.35(17) . . . . ? C35 O32 C32 C33 -1.7(3) . . . . ? C35 O32 C32 C31 178.45(15) . . . . ? C34 C33 C32 O32 -179.27(16) . . . . ? C34 C33 C32 C31 0.6(3) . . . . ? C30 C31 C32 O32 179.76(16) . . . . ? C30 C31 C32 C33 -0.1(3) . . . . ? C32 C31 C30 C29 -1.2(3) . . . . ? C34 C29 C30 C31 1.8(3) . . . . ? C21 C29 C30 C31 -176.84(16) . . . . ? O12 C12 C13 C14 -178.85(16) . . . . ? C11 C12 C13 C14 1.4(3) . . . . ? C9 C14 C13 C12 -0.4(3) . . . . ? C32 C33 C34 C29 0.2(3) . . . . ? C30 C29 C34 C33 -1.4(3) . . . . ? C21 C29 C34 C33 177.26(17) . . . . ? C5 C6 C7 C2 -0.6(3) . . . . ? C8 O5 C5 C4 -1.3(3) . . . . ? C8 O5 C5 C6 178.11(16) . . . . ? C3 C4 C5 O5 -179.82(17) . . . . ? C3 C4 C5 C6 0.8(3) . . . . ? C7 C6 C5 O5 179.55(16) . . . . ? C7 C6 C5 C4 -1.0(3) . . . . ? C6 C7 C2 C3 2.2(3) . . . . ? C6 C7 C2 C1 -176.07(17) . . . . ? C21 C1 C2 C3 -56.1(3) . . . . ? C9 C1 C2 C3 124.73(18) . . . . ? C21 C1 C2 C7 122.1(2) . . . . ? C9 C1 C2 C7 -57.0(2) . . . . ? C22 C23 C24 C25 -0.2(3) . . . . ? O25 C25 C24 C23 -179.17(16) . . . . ? C26 C25 C24 C23 1.8(3) . . . . ? C13 C14 C9 C10 -1.6(2) . . . . ? C13 C14 C9 C1 178.89(16) . . . . ? C11 C10 C9 C14 2.6(2) . . . . ? C11 C10 C9 C1 -177.85(16) . . . . ? C21 C1 C9 C14 -52.8(2) . . . . ? C2 C1 C9 C14 126.41(18) . . . . ? C21 C1 C9 C10 127.72(19) . . . . ? C2 C1 C9 C10 -53.1(2) . . . . ? O25 C25 C26 C27 179.75(17) . . . . ? C24 C25 C26 C27 -1.3(3) . . . . ? C22 C27 C26 C25 -0.8(3) . . . . ? C5 C4 C3 C2 1.0(3) . . . . ? C7 C2 C3 C4 -2.5(3) . . . . ? C1 C2 C3 C4 175.81(17) . . . . ? _diffrn_measured_fraction_theta_max 0.932 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.946 _refine_diff_density_max 0.196 _refine_diff_density_min -0.250 _refine_diff_density_rms 0.048