data_1 _publ_contact_author_name 'LYDIA BRELOT' _publ_contact_author_address ;Institut de Chimie CNRS UMR 7177 Universite de Strasbourg 4, rue Blaise Pascal 67000 STRASBOURG FRANCE ; _publ_contact_author_email djukic@chimie.u-strasbg.fr _publ_contact_author_phone 33-0-390241523 loop_ _publ_author_name _publ_author_address 'DJUKIC, JEAN-PIERRE' ;Institut de Chimie CNRS UMR 7177 Universite de Strasbourg 4, rue Blaise Pascal 67000 STRASBOURG FRANCE ; 'PARKHOMENKO, Ksenia' ;Institut de Chimie CNRS UMR 7177 Universite de Strasbourg 4, rue Blaise Pascal 67000 STRASBOURG FRANCE ; 'ANTHOPOULOS, Thomas' ;Blackett Laboratory Imperial College London South Kensington Campus London SW7 2AZ Great Britain ; 'WOBKENBERG, Paul' ;Blackett Laboratory Imperial College London South Kensington Campus London SW7 2AZ Great Britain ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C34 H34 O2' _chemical_formula_sum 'C34 H34 O2' _chemical_formula_weight 474.61 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 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' 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 9.6702(6) _cell_length_b 14.2059(10) _cell_length_c 11.0365(7) _cell_angle_alpha 90.00 _cell_angle_beta 123.306(4) _cell_angle_gamma 90.00 _cell_volume 1267.10(14) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 6269 _cell_measurement_theta_min 0.998 _cell_measurement_theta_max 27.485 _exptl_crystal_description plate _exptl_crystal_colour brown _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.244 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 508 _exptl_absorpt_coefficient_mu 0.075 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _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 KappaCCD _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10136 _diffrn_reflns_av_R_equivalents 0.0653 _diffrn_reflns_av_sigmaI/netI 0.0714 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.52 _diffrn_reflns_theta_max 27.46 _reflns_number_total 2894 _reflns_number_gt 1850 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'Collect (Nonius B.V., 1998)' _computing_cell_refinement 'Denzo (Nonius B.V., 1998)' _computing_data_reduction 'Denzo (Nonius B.V., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON 98 (Spek, 1998)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2^, conventional R-factors R are based on F, with F set to zero for negative F2^. The threshold expression of F2^ > 2sigma(F2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2^ 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/[\s2^(Fo2^)+(0.0716P)2^+0.0000P] where P=(Fo2^+2Fc2^)/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 2894 _refine_ls_number_parameters 167 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1014 _refine_ls_R_factor_gt 0.0560 _refine_ls_wR_factor_ref 0.1373 _refine_ls_wR_factor_gt 0.1198 _refine_ls_goodness_of_fit_ref 1.017 _refine_ls_restrained_S_all 1.017 _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 -0.22207(15) 0.01974(9) 0.14165(11) 0.0341(4) Uani 1 1 d . . . C1 C -0.3728(2) 0.00960(12) 0.06683(17) 0.0256(4) Uani 1 1 d . . . C2 C -0.5023(2) -0.02241(12) 0.08910(16) 0.0243(4) Uani 1 1 d . . . C3 C -0.5263(2) -0.06057(12) 0.19476(17) 0.0238(4) Uani 1 1 d . . . C4 C -0.6709(2) -0.11528(12) 0.15115(17) 0.0259(4) Uani 1 1 d . . . H4 H -0.7629 -0.1211 0.0538 0.031 Uiso 1 1 calc R . . C5 C -0.6598(2) -0.15806(12) 0.26717(17) 0.0250(4) Uani 1 1 d . . . C6 C -0.7872(2) -0.21977(13) 0.26426(18) 0.0336(5) Uani 1 1 d . . . H6A H -0.8743 -0.2345 0.1635 0.050 Uiso 1 1 calc R . . H6B H -0.8356 -0.1870 0.3105 0.050 Uiso 1 1 calc R . . H6C H -0.7349 -0.2783 0.3168 0.050 Uiso 1 1 calc R . . C7 C -0.5049(2) -0.13177(12) 0.39444(16) 0.0236(4) Uani 1 1 d . . . C8 C -0.4223(2) -0.06549(12) 0.35146(17) 0.0234(4) Uani 1 1 d . . . C9 C -0.2872(2) -0.00924(12) 0.44664(17) 0.0255(4) Uani 1 1 d . . . C10 C -0.2476(2) 0.07556(13) 0.38981(18) 0.0332(5) Uani 1 1 d . . . H10A H -0.1761 0.0569 0.3566 0.050 Uiso 1 1 calc R . . H10B H -0.1905 0.1225 0.4671 0.050 Uiso 1 1 calc R . . H10C H -0.3504 0.1026 0.3086 0.050 Uiso 1 1 calc R . . C11 C -0.1800(2) -0.02436(13) 0.59677(16) 0.0308(4) Uani 1 1 d . . . H11 H -0.0893 0.0181 0.6436 0.037 Uiso 1 1 calc R . . C12 C -0.1823(2) -0.08971(13) 0.68900(18) 0.0323(5) Uani 1 1 d . . . H12 H -0.0861 -0.0899 0.7848 0.039 Uiso 1 1 calc R . . C13 C -0.3030(2) -0.15540(12) 0.66404(17) 0.0265(4) Uani 1 1 d . . . C14 C -0.4496(2) -0.16898(12) 0.53096(16) 0.0263(4) Uani 1 1 d . . . H14 H -0.5253 -0.2106 0.5328 0.032 Uiso 1 1 calc R . . C15 C -0.2706(2) -0.21686(13) 0.79097(17) 0.0310(5) Uani 1 1 d . . . H15 H -0.3738 -0.2536 0.7577 0.037 Uiso 1 1 calc R . . C16 C -0.2318(3) -0.16013(15) 0.92275(19) 0.0466(6) Uani 1 1 d . . . H16A H -0.1302 -0.1239 0.9589 0.070 Uiso 1 1 calc R . . H16B H -0.2167 -0.2029 0.9988 0.070 Uiso 1 1 calc R . . H16C H -0.3236 -0.1170 0.8956 0.070 Uiso 1 1 calc R . . C17 C -0.1330(2) -0.28731(13) 0.83179(19) 0.0381(5) Uani 1 1 d . . . H17A H -0.1636 -0.3265 0.7475 0.057 Uiso 1 1 calc R . . H17B H -0.1164 -0.3273 0.9111 0.057 Uiso 1 1 calc R . . H17C H -0.0303 -0.2534 0.8631 0.057 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 0.0247(7) 0.0509(9) 0.0233(6) 0.0002(6) 0.0110(6) -0.0036(7) C1 0.0238(10) 0.0299(10) 0.0219(8) -0.0009(8) 0.0119(8) -0.0004(8) C2 0.0279(10) 0.0237(9) 0.0222(8) 0.0004(7) 0.0145(8) 0.0015(8) C3 0.0243(10) 0.0254(9) 0.0223(8) -0.0009(7) 0.0131(7) -0.0007(8) C4 0.0237(10) 0.0316(10) 0.0203(8) -0.0010(7) 0.0107(8) -0.0009(8) C5 0.0248(10) 0.0279(10) 0.0238(9) -0.0009(7) 0.0142(8) 0.0003(8) C6 0.0329(11) 0.0386(11) 0.0305(9) -0.0037(8) 0.0182(9) -0.0066(9) C7 0.0253(10) 0.0244(9) 0.0238(9) -0.0004(7) 0.0152(8) 0.0009(8) C8 0.0230(10) 0.0259(9) 0.0225(8) 0.0008(7) 0.0132(8) 0.0022(8) C9 0.0254(10) 0.0290(10) 0.0241(8) -0.0010(8) 0.0148(8) -0.0007(8) C10 0.0381(12) 0.0366(11) 0.0256(9) -0.0046(8) 0.0179(9) -0.0103(9) C11 0.0303(11) 0.0349(11) 0.0249(9) -0.0025(8) 0.0138(8) -0.0054(9) C12 0.0305(11) 0.0391(11) 0.0221(9) -0.0001(8) 0.0111(8) -0.0010(9) C13 0.0262(10) 0.0324(10) 0.0224(9) 0.0017(8) 0.0142(8) 0.0041(8) C14 0.0275(10) 0.0290(10) 0.0266(9) 0.0013(8) 0.0176(8) 0.0011(8) C15 0.0322(11) 0.0389(11) 0.0233(9) 0.0060(8) 0.0162(8) 0.0025(9) C16 0.0620(15) 0.0541(14) 0.0320(10) 0.0092(10) 0.0310(11) 0.0189(12) C17 0.0446(13) 0.0367(11) 0.0397(11) 0.0070(9) 0.0274(10) 0.0082(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 C1 1.2269(19) . ? C1 C2 1.473(2) 3_455 ? C1 C2 1.474(2) . ? C2 C3 1.416(2) . ? C2 C1 1.473(2) 3_455 ? C3 C4 1.432(2) . ? C3 C8 1.448(2) . ? C4 C5 1.368(2) . ? C4 H4 0.9500 . ? C5 C7 1.430(2) . ? C5 C6 1.497(2) . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 C14 1.397(2) . ? C7 C8 1.472(2) . ? C8 C9 1.393(2) . ? C9 C11 1.407(2) . ? C9 C10 1.502(2) . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 C12 1.387(2) . ? C11 H11 0.9500 . ? C12 C13 1.399(2) . ? C12 H12 0.9500 . ? C13 C14 1.385(2) . ? C13 C15 1.530(2) . ? C14 H14 0.9500 . ? C15 C16 1.519(2) . ? C15 C17 1.522(3) . ? C15 H15 1.0000 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 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 O1 C1 C2 132.88(15) . 3_455 ? O1 C1 C2 136.72(15) . . ? C2 C1 C2 90.36(13) 3_455 . ? C3 C2 C1 127.54(16) . 3_455 ? C3 C2 C1 142.54(16) . . ? C1 C2 C1 89.64(13) 3_455 . ? C2 C3 C4 120.14(14) . . ? C2 C3 C8 132.97(16) . . ? C4 C3 C8 106.55(13) . . ? C5 C4 C3 111.51(14) . . ? C5 C4 H4 124.2 . . ? C3 C4 H4 124.2 . . ? C4 C5 C7 107.73(15) . . ? C4 C5 C6 126.85(16) . . ? C7 C5 C6 125.41(15) . . ? C5 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C5 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C14 C7 C5 122.32(16) . . ? C14 C7 C8 129.47(15) . . ? C5 C7 C8 108.17(14) . . ? C9 C8 C3 128.42(15) . . ? C9 C8 C7 125.04(14) . . ? C3 C8 C7 105.77(14) . . ? C8 C9 C11 125.42(16) . . ? C8 C9 C10 119.59(14) . . ? C11 C9 C10 114.99(15) . . ? 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 . . ? C12 C11 C9 131.94(17) . . ? C12 C11 H11 114.0 . . ? C9 C11 H11 114.0 . . ? C11 C12 C13 130.53(16) . . ? C11 C12 H12 114.7 . . ? C13 C12 H12 114.7 . . ? C14 C13 C12 124.02(15) . . ? C14 C13 C15 117.88(16) . . ? C12 C13 C15 118.10(15) . . ? C13 C14 C7 130.85(17) . . ? C13 C14 H14 114.6 . . ? C7 C14 H14 114.6 . . ? C16 C15 C17 110.46(14) . . ? C16 C15 C13 113.12(15) . . ? C17 C15 C13 110.66(14) . . ? C16 C15 H15 107.4 . . ? C17 C15 H15 107.4 . . ? C13 C15 H15 107.4 . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C15 C17 H17A 109.5 . . ? C15 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C15 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 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 O1 C1 C2 C3 -4.3(4) . . . . ? C2 C1 C2 C3 173.5(3) 3_455 . . . ? O1 C1 C2 C1 -177.9(3) . . . 3_455 ? C2 C1 C2 C1 0.0 3_455 . . 3_455 ? C1 C2 C3 C4 17.4(3) 3_455 . . . ? C1 C2 C3 C4 -154.4(2) . . . . ? C1 C2 C3 C8 -170.28(17) 3_455 . . . ? C1 C2 C3 C8 17.9(4) . . . . ? C2 C3 C4 C5 170.44(15) . . . . ? C8 C3 C4 C5 -3.71(19) . . . . ? C3 C4 C5 C7 0.6(2) . . . . ? C3 C4 C5 C6 179.32(16) . . . . ? C4 C5 C7 C14 -175.30(15) . . . . ? C6 C5 C7 C14 5.9(3) . . . . ? C4 C5 C7 C8 2.76(19) . . . . ? C6 C5 C7 C8 -176.00(16) . . . . ? C2 C3 C8 C9 21.8(3) . . . . ? C4 C3 C8 C9 -165.08(17) . . . . ? C2 C3 C8 C7 -167.93(18) . . . . ? C4 C3 C8 C7 5.15(18) . . . . ? C14 C7 C8 C9 -16.4(3) . . . . ? C5 C7 C8 C9 165.72(16) . . . . ? C14 C7 C8 C3 172.94(16) . . . . ? C5 C7 C8 C3 -4.93(18) . . . . ? C3 C8 C9 C11 -172.49(17) . . . . ? C7 C8 C9 C11 19.0(3) . . . . ? C3 C8 C9 C10 7.7(3) . . . . ? C7 C8 C9 C10 -160.80(16) . . . . ? C8 C9 C11 C12 -4.7(3) . . . . ? C10 C9 C11 C12 175.08(19) . . . . ? C9 C11 C12 C13 -8.0(3) . . . . ? C11 C12 C13 C14 2.4(3) . . . . ? C11 C12 C13 C15 -178.34(18) . . . . ? C12 C13 C14 C7 7.0(3) . . . . ? C15 C13 C14 C7 -172.24(17) . . . . ? C5 C7 C14 C13 177.21(17) . . . . ? C8 C7 C14 C13 -0.4(3) . . . . ? C14 C13 C15 C16 -125.90(18) . . . . ? C12 C13 C15 C16 54.8(2) . . . . ? C14 C13 C15 C17 109.55(18) . . . . ? C12 C13 C15 C17 -69.8(2) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.46 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.209 _refine_diff_density_min -0.277 _refine_diff_density_rms 0.051