# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_global #============================================================================== data_wa915 #TrackingRef 'deposit.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C30 H30 B2' _chemical_formula_sum 'C30 H30 B2' _chemical_formula_weight 412.16 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' B B 0.0013 0.0007 '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 12.8350(12) _cell_length_b 22.061(3) _cell_length_c 9.0732(8) _cell_angle_alpha 90.00 _cell_angle_beta 107.478(7) _cell_angle_gamma 90.00 _cell_volume 2450.5(5) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 5236 _cell_measurement_theta_min 3.3 _cell_measurement_theta_max 25.9 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.117 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 880 _exptl_absorpt_coefficient_mu 0.062 _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 'STOE IPDS II two-circle-diffractometer' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 16322 _diffrn_reflns_av_R_equivalents 0.0948 _diffrn_reflns_av_sigmaI/netI 0.1413 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 3.23 _diffrn_reflns_theta_max 25.03 _reflns_number_total 4331 _reflns_number_gt 2228 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'X-Area (Stoe & Cie, 2001)' _computing_cell_refinement 'X-Area (Stoe & Cie, 2001)' _computing_data_reduction 'X-Area (Stoe & Cie, 2001)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP in SHELXTL-Plus (Sheldrick, 1991)' _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0576P)^2^] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0120(13) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4331 _refine_ls_number_parameters 296 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1454 _refine_ls_R_factor_gt 0.0717 _refine_ls_wR_factor_ref 0.1646 _refine_ls_wR_factor_gt 0.1390 _refine_ls_goodness_of_fit_ref 0.913 _refine_ls_restrained_S_all 0.913 _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 B1 B 0.2561(3) 0.4008(2) 0.7019(4) 0.0293(9) Uani 1 1 d . . . B2 B 0.4626(3) 0.37049(19) 0.6294(4) 0.0298(9) Uani 1 1 d . . . C1 C 0.1472(3) 0.40610(17) 0.7482(3) 0.0311(8) Uani 1 1 d . . . C2 C 0.1061(3) 0.35365(18) 0.8008(3) 0.0344(8) Uani 1 1 d . . . C3 C 0.0128(3) 0.3580(2) 0.8496(4) 0.0387(9) Uani 1 1 d . . . H3 H -0.0151 0.3226 0.8839 0.046 Uiso 1 1 calc R . . C4 C -0.0398(3) 0.4129(2) 0.8490(3) 0.0391(10) Uani 1 1 d . . . C5 C -0.0007(3) 0.4637(2) 0.7943(3) 0.0383(9) Uani 1 1 d . . . H5 H -0.0375 0.5013 0.7910 0.046 Uiso 1 1 calc R . . C6 C 0.0919(3) 0.46094(18) 0.7437(3) 0.0338(8) Uani 1 1 d . . . C7 C 0.1611(3) 0.2932(2) 0.8021(4) 0.0505(10) Uani 1 1 d . . . H7A H 0.1315 0.2638 0.8598 0.076 Uiso 1 1 calc R . . H7B H 0.2399 0.2975 0.8515 0.076 Uiso 1 1 calc R . . H7C H 0.1477 0.2789 0.6957 0.076 Uiso 1 1 calc R . . C8 C -0.1391(3) 0.4162(3) 0.9076(4) 0.0553(13) Uani 1 1 d . . . H8A H -0.1684 0.4575 0.8948 0.083 Uiso 1 1 calc R . . H8B H -0.1177 0.4051 1.0173 0.083 Uiso 1 1 calc R . . H8C H -0.1952 0.3880 0.8486 0.083 Uiso 1 1 calc R . . C9 C 0.1313(3) 0.5169(2) 0.6817(4) 0.0433(9) Uani 1 1 d . . . H9A H 0.2113 0.5182 0.7181 0.065 Uiso 1 1 calc R . . H9B H 0.1019 0.5530 0.7181 0.065 Uiso 1 1 calc R . . H9C H 0.1063 0.5160 0.5685 0.065 Uiso 1 1 calc R . . C21 C 0.2529(3) 0.38578(17) 0.5324(3) 0.0301(8) Uani 1 1 d . . . C22 C 0.1538(3) 0.38540(19) 0.4141(4) 0.0374(9) Uani 1 1 d . . . H22 H 0.0880 0.3939 0.4379 0.045 Uiso 1 1 calc R . . C23 C 0.1496(3) 0.37280(19) 0.2619(4) 0.0413(9) Uani 1 1 d . . . H23 H 0.0819 0.3739 0.1819 0.050 Uiso 1 1 calc R . . C24 C 0.2447(3) 0.3587(2) 0.2285(4) 0.0414(10) Uani 1 1 d . . . H24 H 0.2422 0.3495 0.1252 0.050 Uiso 1 1 calc R . . C25 C 0.3446(3) 0.35789(19) 0.3450(4) 0.0374(9) Uani 1 1 d . . . H25 H 0.4092 0.3476 0.3202 0.045 Uiso 1 1 calc R . . C26 C 0.3510(3) 0.37194(17) 0.4979(3) 0.0294(8) Uani 1 1 d . . . C31 C 0.3686(3) 0.40910(17) 0.8277(3) 0.0286(8) Uani 1 1 d . . . C32 C 0.3755(3) 0.42945(18) 0.9759(3) 0.0346(8) Uani 1 1 d . . . H32 H 0.3106 0.4405 0.9989 0.042 Uiso 1 1 calc R . . C33 C 0.4755(3) 0.43385(19) 1.0906(4) 0.0387(9) Uani 1 1 d . . . H33 H 0.4784 0.4485 1.1902 0.046 Uiso 1 1 calc R . . C34 C 0.5698(3) 0.41697(19) 1.0599(4) 0.0398(9) Uani 1 1 d . . . H34 H 0.6378 0.4192 1.1389 0.048 Uiso 1 1 calc R . . C35 C 0.5657(3) 0.39653(19) 0.9129(4) 0.0399(10) Uani 1 1 d . . . H35 H 0.6315 0.3850 0.8927 0.048 Uiso 1 1 calc R . . C36 C 0.4666(2) 0.39268(17) 0.7945(3) 0.0302(8) Uani 1 1 d . . . C41 C 0.5684(3) 0.34557(17) 0.5955(3) 0.0311(8) Uani 1 1 d . . . C42 C 0.5899(3) 0.28331(19) 0.6091(4) 0.0381(9) Uani 1 1 d . . . C43 C 0.6819(3) 0.2594(2) 0.5794(4) 0.0456(10) Uani 1 1 d . . . H43 H 0.6950 0.2170 0.5895 0.055 Uiso 1 1 calc R . . C44 C 0.7551(3) 0.2963(2) 0.5353(4) 0.0412(9) Uani 1 1 d . . . C45 C 0.7345(3) 0.3582(2) 0.5219(4) 0.0403(9) Uani 1 1 d . . . H45 H 0.7836 0.3840 0.4912 0.048 Uiso 1 1 calc R . . C46 C 0.6435(3) 0.38359(18) 0.5524(3) 0.0349(9) Uani 1 1 d . . . C47 C 0.5119(4) 0.2409(2) 0.6558(5) 0.0557(11) Uani 1 1 d . . . H47A H 0.4558 0.2267 0.5630 0.084 Uiso 1 1 calc R . . H47B H 0.4769 0.2627 0.7225 0.084 Uiso 1 1 calc R . . H47C H 0.5525 0.2062 0.7118 0.084 Uiso 1 1 calc R . . C48 C 0.8545(3) 0.2699(3) 0.5021(5) 0.0643(14) Uani 1 1 d . . . H48A H 0.8330 0.2523 0.3981 0.096 Uiso 1 1 calc R . . H48B H 0.8864 0.2382 0.5780 0.096 Uiso 1 1 calc R . . H48C H 0.9085 0.3020 0.5086 0.096 Uiso 1 1 calc R . . C49 C 0.6255(3) 0.4514(2) 0.5419(5) 0.0505(10) Uani 1 1 d . . . H49A H 0.6886 0.4712 0.5229 0.076 Uiso 1 1 calc R . . H49B H 0.6166 0.4664 0.6391 0.076 Uiso 1 1 calc R . . H49C H 0.5595 0.4606 0.4568 0.076 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 B1 0.0253(19) 0.030(2) 0.0337(18) -0.0008(16) 0.0107(15) 0.0019(17) B2 0.025(2) 0.030(2) 0.0358(18) 0.0067(16) 0.0115(15) 0.0001(17) C1 0.0246(16) 0.045(2) 0.0250(14) -0.0030(14) 0.0088(12) -0.0007(16) C2 0.0313(19) 0.042(2) 0.0317(15) -0.0013(15) 0.0117(14) -0.0032(17) C3 0.0306(19) 0.053(3) 0.0344(17) -0.0029(17) 0.0127(14) -0.0119(18) C4 0.0225(18) 0.064(3) 0.0336(17) -0.0090(17) 0.0120(14) -0.0030(18) C5 0.0292(19) 0.048(3) 0.0375(16) -0.0036(17) 0.0104(14) 0.0063(17) C6 0.0248(18) 0.046(3) 0.0309(15) -0.0026(15) 0.0092(13) 0.0005(16) C7 0.056(3) 0.043(3) 0.059(2) 0.000(2) 0.0280(19) -0.001(2) C8 0.032(2) 0.090(4) 0.049(2) -0.011(2) 0.0204(17) -0.005(2) C9 0.038(2) 0.046(3) 0.0488(19) 0.0030(18) 0.0169(16) 0.0019(19) C21 0.0253(17) 0.034(2) 0.0318(15) 0.0025(14) 0.0092(13) 0.0014(15) C22 0.0269(18) 0.047(3) 0.0384(17) 0.0002(16) 0.0095(14) 0.0083(17) C23 0.037(2) 0.046(3) 0.0359(18) 0.0001(16) 0.0042(15) 0.0024(18) C24 0.048(2) 0.050(3) 0.0272(16) -0.0017(16) 0.0121(15) 0.0007(19) C25 0.0332(19) 0.047(3) 0.0368(17) -0.0038(16) 0.0173(15) 0.0025(18) C26 0.0290(17) 0.034(2) 0.0286(15) 0.0007(14) 0.0130(13) 0.0003(15) C31 0.0294(17) 0.030(2) 0.0300(15) 0.0020(14) 0.0143(13) 0.0007(15) C32 0.0307(18) 0.041(2) 0.0337(16) -0.0018(16) 0.0120(14) -0.0003(17) C33 0.040(2) 0.044(3) 0.0326(16) -0.0064(16) 0.0111(15) -0.0066(18) C34 0.0304(19) 0.049(3) 0.0331(16) -0.0014(17) -0.0014(14) -0.0065(18) C35 0.0217(17) 0.054(3) 0.0419(18) 0.0061(17) 0.0068(14) 0.0010(17) C36 0.0206(16) 0.035(2) 0.0356(16) 0.0032(15) 0.0095(13) -0.0013(15) C41 0.0265(17) 0.037(2) 0.0322(16) 0.0000(15) 0.0124(13) 0.0031(16) C42 0.0338(19) 0.037(2) 0.0464(19) -0.0048(17) 0.0159(16) 0.0004(18) C43 0.035(2) 0.045(3) 0.055(2) -0.0152(19) 0.0110(17) 0.0050(19) C44 0.0287(19) 0.048(3) 0.0482(19) -0.0095(18) 0.0139(16) 0.0061(18) C45 0.0266(18) 0.057(3) 0.0428(18) -0.0031(18) 0.0179(15) -0.0040(18) C46 0.0301(18) 0.043(2) 0.0342(16) 0.0033(16) 0.0135(14) 0.0017(17) C47 0.053(3) 0.045(3) 0.076(3) 0.000(2) 0.029(2) 0.000(2) C48 0.039(2) 0.077(4) 0.077(3) -0.025(3) 0.018(2) 0.015(2) C49 0.044(2) 0.050(3) 0.064(2) 0.009(2) 0.0264(19) 0.004(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 B1 C31 1.560(5) . ? B1 C21 1.562(4) . ? B1 C1 1.580(5) . ? B2 C36 1.562(5) . ? B2 C26 1.566(5) . ? B2 C41 1.578(5) . ? C1 C6 1.397(5) . ? C1 C2 1.413(5) . ? C2 C3 1.399(5) . ? C2 C7 1.508(6) . ? C3 C4 1.385(6) . ? C3 H3 0.9500 . ? C4 C5 1.380(6) . ? C4 C8 1.524(5) . ? C5 C6 1.399(5) . ? C5 H5 0.9500 . ? C6 C9 1.506(5) . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C21 C22 1.396(4) . ? C21 C26 1.418(4) . ? C22 C23 1.395(5) . ? C22 H22 0.9500 . ? C23 C24 1.378(5) . ? C23 H23 0.9500 . ? C24 C25 1.396(5) . ? C24 H24 0.9500 . ? C25 C26 1.399(4) . ? C25 H25 0.9500 . ? C31 C32 1.394(4) . ? C31 C36 1.426(4) . ? C32 C33 1.392(5) . ? C32 H32 0.9500 . ? C33 C34 1.372(5) . ? C33 H33 0.9500 . ? C34 C35 1.395(5) . ? C34 H34 0.9500 . ? C35 C36 1.400(4) . ? C35 H35 0.9500 . ? C41 C42 1.399(5) . ? C41 C46 1.418(5) . ? C42 C43 1.391(5) . ? C42 C47 1.520(6) . ? C43 C44 1.390(6) . ? C43 H43 0.9500 . ? C44 C45 1.390(6) . ? C44 C48 1.513(5) . ? C45 C46 1.395(5) . ? C45 H45 0.9500 . ? C46 C49 1.513(6) . ? C47 H47A 0.9800 . ? C47 H47B 0.9800 . ? C47 H47C 0.9800 . ? C48 H48A 0.9800 . ? C48 H48B 0.9800 . ? C48 H48C 0.9800 . ? C49 H49A 0.9800 . ? C49 H49B 0.9800 . ? C49 H49C 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 C31 B1 C21 119.4(3) . . ? C31 B1 C1 119.7(3) . . ? C21 B1 C1 120.9(3) . . ? C36 B2 C26 118.9(3) . . ? C36 B2 C41 120.9(3) . . ? C26 B2 C41 120.2(3) . . ? C6 C1 C2 118.7(3) . . ? C6 C1 B1 122.6(3) . . ? C2 C1 B1 118.6(3) . . ? C3 C2 C1 119.5(4) . . ? C3 C2 C7 120.1(4) . . ? C1 C2 C7 120.4(3) . . ? C4 C3 C2 121.4(4) . . ? C4 C3 H3 119.3 . . ? C2 C3 H3 119.3 . . ? C5 C4 C3 118.9(3) . . ? C5 C4 C8 121.3(4) . . ? C3 C4 C8 119.8(4) . . ? C4 C5 C6 121.2(4) . . ? C4 C5 H5 119.4 . . ? C6 C5 H5 119.4 . . ? C1 C6 C5 120.2(4) . . ? C1 C6 C9 119.8(3) . . ? C5 C6 C9 120.0(4) . . ? C2 C7 H7A 109.5 . . ? C2 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C2 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C4 C8 H8A 109.5 . . ? C4 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C4 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C6 C9 H9A 109.5 . . ? C6 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C6 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C22 C21 C26 119.6(3) . . ? C22 C21 B1 120.4(3) . . ? C26 C21 B1 120.0(3) . . ? C23 C22 C21 121.1(3) . . ? C23 C22 H22 119.4 . . ? C21 C22 H22 119.4 . . ? C24 C23 C22 119.3(3) . . ? C24 C23 H23 120.3 . . ? C22 C23 H23 120.3 . . ? C23 C24 C25 120.6(3) . . ? C23 C24 H24 119.7 . . ? C25 C24 H24 119.7 . . ? C24 C25 C26 121.0(3) . . ? C24 C25 H25 119.5 . . ? C26 C25 H25 119.5 . . ? C25 C26 C21 118.3(3) . . ? C25 C26 B2 121.2(3) . . ? C21 C26 B2 120.4(3) . . ? C32 C31 C36 118.8(3) . . ? C32 C31 B1 121.4(3) . . ? C36 C31 B1 119.8(3) . . ? C33 C32 C31 121.4(3) . . ? C33 C32 H32 119.3 . . ? C31 C32 H32 119.3 . . ? C34 C33 C32 120.0(3) . . ? C34 C33 H33 120.0 . . ? C32 C33 H33 120.0 . . ? C33 C34 C35 120.0(3) . . ? C33 C34 H34 120.0 . . ? C35 C34 H34 120.0 . . ? C34 C35 C36 121.2(3) . . ? C34 C35 H35 119.4 . . ? C36 C35 H35 119.4 . . ? C35 C36 C31 118.6(3) . . ? C35 C36 B2 121.0(3) . . ? C31 C36 B2 120.4(3) . . ? C42 C41 C46 118.2(3) . . ? C42 C41 B2 118.9(3) . . ? C46 C41 B2 122.9(3) . . ? C43 C42 C41 120.8(4) . . ? C43 C42 C47 119.3(4) . . ? C41 C42 C47 119.9(3) . . ? C44 C43 C42 121.3(4) . . ? C44 C43 H43 119.4 . . ? C42 C43 H43 119.4 . . ? C45 C44 C43 118.3(3) . . ? C45 C44 C48 120.8(4) . . ? C43 C44 C48 121.0(4) . . ? C44 C45 C46 121.7(3) . . ? C44 C45 H45 119.1 . . ? C46 C45 H45 119.1 . . ? C45 C46 C41 119.7(4) . . ? C45 C46 C49 120.3(3) . . ? C41 C46 C49 119.9(3) . . ? C42 C47 H47A 109.5 . . ? C42 C47 H47B 109.5 . . ? H47A C47 H47B 109.5 . . ? C42 C47 H47C 109.5 . . ? H47A C47 H47C 109.5 . . ? H47B C47 H47C 109.5 . . ? C44 C48 H48A 109.5 . . ? C44 C48 H48B 109.5 . . ? H48A C48 H48B 109.5 . . ? C44 C48 H48C 109.5 . . ? H48A C48 H48C 109.5 . . ? H48B C48 H48C 109.5 . . ? C46 C49 H49A 109.5 . . ? C46 C49 H49B 109.5 . . ? H49A C49 H49B 109.5 . . ? C46 C49 H49C 109.5 . . ? H49A C49 H49C 109.5 . . ? H49B C49 H49C 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 C31 B1 C1 C6 90.3(4) . . . . ? C21 B1 C1 C6 -91.2(4) . . . . ? C31 B1 C1 C2 -87.7(4) . . . . ? C21 B1 C1 C2 90.9(4) . . . . ? C6 C1 C2 C3 -1.2(5) . . . . ? B1 C1 C2 C3 176.9(3) . . . . ? C6 C1 C2 C7 177.8(3) . . . . ? B1 C1 C2 C7 -4.1(5) . . . . ? C1 C2 C3 C4 -0.7(5) . . . . ? C7 C2 C3 C4 -179.7(3) . . . . ? C2 C3 C4 C5 2.1(5) . . . . ? C2 C3 C4 C8 -178.1(3) . . . . ? C3 C4 C5 C6 -1.6(5) . . . . ? C8 C4 C5 C6 178.6(3) . . . . ? C2 C1 C6 C5 1.6(4) . . . . ? B1 C1 C6 C5 -176.3(3) . . . . ? C2 C1 C6 C9 -177.4(3) . . . . ? B1 C1 C6 C9 4.6(5) . . . . ? C4 C5 C6 C1 -0.2(5) . . . . ? C4 C5 C6 C9 178.8(3) . . . . ? C31 B1 C21 C22 -172.2(4) . . . . ? C1 B1 C21 C22 9.2(6) . . . . ? C31 B1 C21 C26 8.4(5) . . . . ? C1 B1 C21 C26 -170.2(3) . . . . ? C26 C21 C22 C23 -1.3(6) . . . . ? B1 C21 C22 C23 179.2(4) . . . . ? C21 C22 C23 C24 1.9(6) . . . . ? C22 C23 C24 C25 -0.9(6) . . . . ? C23 C24 C25 C26 -0.8(7) . . . . ? C24 C25 C26 C21 1.4(6) . . . . ? C24 C25 C26 B2 179.4(4) . . . . ? C22 C21 C26 C25 -0.4(6) . . . . ? B1 C21 C26 C25 179.1(4) . . . . ? C22 C21 C26 B2 -178.4(4) . . . . ? B1 C21 C26 B2 1.0(5) . . . . ? C36 B2 C26 C25 174.1(3) . . . . ? C41 B2 C26 C25 -7.3(5) . . . . ? C36 B2 C26 C21 -7.9(5) . . . . ? C41 B2 C26 C21 170.7(3) . . . . ? C21 B1 C31 C32 172.3(3) . . . . ? C1 B1 C31 C32 -9.1(5) . . . . ? C21 B1 C31 C36 -11.0(5) . . . . ? C1 B1 C31 C36 167.6(3) . . . . ? C36 C31 C32 C33 -0.1(6) . . . . ? B1 C31 C32 C33 176.6(4) . . . . ? C31 C32 C33 C34 -1.2(6) . . . . ? C32 C33 C34 C35 1.3(6) . . . . ? C33 C34 C35 C36 -0.1(6) . . . . ? C34 C35 C36 C31 -1.1(6) . . . . ? C34 C35 C36 B2 179.3(4) . . . . ? C32 C31 C36 C35 1.2(5) . . . . ? B1 C31 C36 C35 -175.5(4) . . . . ? C32 C31 C36 B2 -179.2(3) . . . . ? B1 C31 C36 B2 4.1(5) . . . . ? C26 B2 C36 C35 -175.2(4) . . . . ? C41 B2 C36 C35 6.2(5) . . . . ? C26 B2 C36 C31 5.2(5) . . . . ? C41 B2 C36 C31 -173.4(3) . . . . ? C36 B2 C41 C42 92.0(4) . . . . ? C26 B2 C41 C42 -86.6(4) . . . . ? C36 B2 C41 C46 -87.7(4) . . . . ? C26 B2 C41 C46 93.7(4) . . . . ? C46 C41 C42 C43 -0.7(5) . . . . ? B2 C41 C42 C43 179.6(3) . . . . ? C46 C41 C42 C47 179.7(3) . . . . ? B2 C41 C42 C47 0.0(5) . . . . ? C41 C42 C43 C44 -0.1(5) . . . . ? C47 C42 C43 C44 179.5(3) . . . . ? C42 C43 C44 C45 0.2(5) . . . . ? C42 C43 C44 C48 -179.6(4) . . . . ? C43 C44 C45 C46 0.4(5) . . . . ? C48 C44 C45 C46 -179.8(3) . . . . ? C44 C45 C46 C41 -1.2(5) . . . . ? C44 C45 C46 C49 178.0(3) . . . . ? C42 C41 C46 C45 1.3(5) . . . . ? B2 C41 C46 C45 -179.0(3) . . . . ? C42 C41 C46 C49 -177.8(3) . . . . ? B2 C41 C46 C49 1.9(5) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.222 _refine_diff_density_min -0.251 _refine_diff_density_rms 0.056 _database_code_depnum_ccdc_archive 'CCDC 922259' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_global data_wa1028 #TrackingRef 'deposit.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C46 H62 B2 Li2 O4' _chemical_formula_sum 'C46 H62 B2 Li2 O4' _chemical_formula_weight 714.46 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' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Li Li -0.0003 0.0001 '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 _symmetry_space_group_name_Hall '-P 2yn' 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 10.5785(15) _cell_length_b 11.7290(16) _cell_length_c 17.244(3) _cell_angle_alpha 90.00 _cell_angle_beta 104.849(12) _cell_angle_gamma 90.00 _cell_volume 2068.1(5) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 3089 _cell_measurement_theta_min 3.7 _cell_measurement_theta_max 25.2 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.31 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.147 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 772 _exptl_absorpt_coefficient_mu 0.069 _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 'STOE IPDS II two-circle-diffractometer' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 5231 _diffrn_reflns_av_R_equivalents 0.0622 _diffrn_reflns_av_sigmaI/netI 0.0547 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.05 _diffrn_reflns_theta_max 25.03 _reflns_number_total 3656 _reflns_number_gt 2597 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'X-Area (Stoe & Cie, 2001)' _computing_cell_refinement 'X-Area (Stoe & Cie, 2001)' _computing_data_reduction 'X-Area (Stoe & Cie, 2001)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008) ' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008) ' _computing_molecular_graphics 'XP (Sheldrick, 2008)' _computing_publication_material SHELXL97 _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^)+(0.0959P)^2^+0.1223P] 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 3656 _refine_ls_number_parameters 247 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0833 _refine_ls_R_factor_gt 0.0562 _refine_ls_wR_factor_ref 0.1682 _refine_ls_wR_factor_gt 0.1600 _refine_ls_goodness_of_fit_ref 1.101 _refine_ls_restrained_S_all 1.101 _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 Li1 Li 0.1441(3) 0.59857(19) 0.55128(17) 0.0322(7) Uani 1 1 d . . . O1 O 0.18297(14) 0.76420(8) 0.56529(8) 0.0414(4) Uani 1 1 d . . . O2 O 0.32476(13) 0.56285(9) 0.61480(7) 0.0347(4) Uani 1 1 d . A . B1 B 0.0443(2) 0.50434(12) 0.42171(10) 0.0261(5) Uani 1 1 d . . . C1 C 0.08474(18) 0.51088(12) 0.33709(10) 0.0291(4) Uani 1 1 d . . . C2 C 0.1487(2) 0.60609(14) 0.31554(11) 0.0372(5) Uani 1 1 d . . . C3 C 0.1747(2) 0.61208(17) 0.23942(12) 0.0462(6) Uani 1 1 d . . . H3 H 0.2154 0.6784 0.2255 0.055 Uiso 1 1 calc R . . C4 C 0.1426(2) 0.52431(17) 0.18458(11) 0.0451(5) Uani 1 1 d . . . C5 C 0.0830(2) 0.43005(15) 0.20600(11) 0.0421(5) Uani 1 1 d . . . H5 H 0.0605 0.3687 0.1690 0.051 Uiso 1 1 calc R . . C6 C 0.05421(19) 0.42109(12) 0.28086(10) 0.0330(5) Uani 1 1 d . . . C7 C 0.1933(2) 0.70306(15) 0.37159(13) 0.0486(6) Uani 1 1 d . . . H7A H 0.1174 0.7395 0.3839 0.073 Uiso 1 1 calc R . . H7B H 0.2395 0.7587 0.3465 0.073 Uiso 1 1 calc R . . H7C H 0.2524 0.6747 0.4213 0.073 Uiso 1 1 calc R . . C8 C 0.1688(3) 0.5337(3) 0.10228(14) 0.0761(8) Uani 1 1 d . . . H8A H 0.1980 0.4597 0.0870 0.114 Uiso 1 1 calc R . . H8B H 0.2370 0.5908 0.1038 0.114 Uiso 1 1 calc R . . H8C H 0.0885 0.5566 0.0629 0.114 Uiso 1 1 calc R . . C9 C -0.0130(2) 0.31443(12) 0.29746(11) 0.0397(5) Uani 1 1 d . . . H9A H -0.0266 0.2632 0.2512 0.060 Uiso 1 1 calc R . . H9B H -0.0977 0.3342 0.3071 0.060 Uiso 1 1 calc R . . H9C H 0.0415 0.2763 0.3449 0.060 Uiso 1 1 calc R . . C31 C 0.10099(17) 0.41899(10) 0.48678(9) 0.0257(4) Uani 1 1 d . . . C32 C 0.20319(18) 0.34010(11) 0.48038(10) 0.0286(4) Uani 1 1 d . . . H32 H 0.2323 0.3414 0.4327 0.034 Uiso 1 1 calc R . . C33 C 0.2594(2) 0.26497(12) 0.53797(11) 0.0355(5) Uani 1 1 d . . . H33 H 0.3277 0.2169 0.5307 0.043 Uiso 1 1 calc R . . C34 C 0.2167(2) 0.25727(11) 0.60977(9) 0.0330(5) Uani 1 1 d . . . H34 H 0.2537 0.2025 0.6497 0.040 Uiso 1 1 calc R . . C35 C 0.12159(18) 0.33016(10) 0.61996(10) 0.0275(4) Uani 1 1 d . . . H35 H 0.0953 0.3255 0.6686 0.033 Uiso 1 1 calc R . . C36 C 0.05950(17) 0.41250(10) 0.56238(9) 0.0242(4) Uani 1 1 d . . . C41 C 0.0891(2) 0.85437(13) 0.53578(12) 0.0458(6) Uani 1 1 d . . . H41A H -0.0014 0.8275 0.5308 0.055 Uiso 1 1 calc R . . H41B H 0.0962 0.8824 0.4829 0.055 Uiso 1 1 calc R . . C42 C 0.1255(3) 0.94414(14) 0.59732(15) 0.0622(8) Uani 1 1 d . . . H42A H 0.0878 0.9285 0.6432 0.075 Uiso 1 1 calc R . . H42B H 0.0953 1.0199 0.5747 0.075 Uiso 1 1 calc R . . C43 C 0.2743(2) 0.93858(13) 0.62298(15) 0.0563(8) Uani 1 1 d . . . H43A H 0.3136 0.9894 0.5897 0.068 Uiso 1 1 calc R . . H43B H 0.3082 0.9598 0.6801 0.068 Uiso 1 1 calc R . . C44 C 0.3011(3) 0.81898(13) 0.60983(18) 0.0727(11) Uani 1 1 d . . . H44A H 0.3689 0.8136 0.5797 0.087 Uiso 1 1 calc R . . H44B H 0.3343 0.7802 0.6621 0.087 Uiso 1 1 calc R . . C51 C 0.4355(2) 0.55015(16) 0.58140(14) 0.0483(6) Uani 1 1 d . . . H51A H 0.4325 0.6054 0.5376 0.058 Uiso 0.512(9) 1 calc PR A 1 H51B H 0.4415 0.4718 0.5613 0.058 Uiso 0.512(9) 1 calc PR A 1 H51C H 0.4117 0.5003 0.5335 0.058 Uiso 0.488(9) 1 calc PR A 2 H51D H 0.4609 0.6256 0.5644 0.058 Uiso 0.488(9) 1 calc PR A 2 C52 C 0.5507(7) 0.5766(6) 0.6566(4) 0.084(2) Uiso 0.512(9) 1 d P A 1 H52A H 0.6331 0.5417 0.6510 0.100 Uiso 0.512(9) 1 calc PR A 1 H52B H 0.5637 0.6599 0.6641 0.100 Uiso 0.512(9) 1 calc PR A 1 C52' C 0.5375(8) 0.5041(7) 0.6365(4) 0.089(3) Uiso 0.488(9) 1 d P A 2 H52C H 0.6207 0.5398 0.6330 0.107 Uiso 0.488(9) 1 calc PR A 2 H52D H 0.5428 0.4211 0.6276 0.107 Uiso 0.488(9) 1 calc PR A 2 C53 C 0.5113(3) 0.5281(2) 0.72093(18) 0.0797(10) Uani 1 1 d . . . H53A H 0.5494 0.5704 0.7712 0.096 Uiso 0.512(9) 1 calc PR A 1 H53B H 0.5393 0.4475 0.7285 0.096 Uiso 0.512(9) 1 calc PR A 1 H53C H 0.5425 0.4647 0.7589 0.096 Uiso 0.488(9) 1 calc PR A 2 H53D H 0.5528 0.6001 0.7445 0.096 Uiso 0.488(9) 1 calc PR A 2 C54 C 0.3668(2) 0.53666(17) 0.69893(12) 0.0492(6) Uani 1 1 d . A . H54A H 0.3280 0.4636 0.7101 0.059 Uiso 1 1 calc R . . H54B H 0.3386 0.5974 0.7307 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 Li1 0.0299(18) 0.0315(11) 0.0316(15) -0.0077(10) 0.0011(11) -0.0031(11) O1 0.0329(9) 0.0293(5) 0.0523(8) -0.0037(5) -0.0066(6) -0.0025(5) O2 0.0261(8) 0.0418(5) 0.0351(7) -0.0002(5) 0.0059(5) 0.0029(5) B1 0.0244(11) 0.0316(8) 0.0214(9) -0.0031(6) 0.0042(7) -0.0018(8) C1 0.0257(11) 0.0347(7) 0.0253(9) 0.0055(6) 0.0040(7) 0.0078(7) C2 0.0339(12) 0.0485(8) 0.0301(10) 0.0088(7) 0.0097(7) 0.0049(8) C3 0.0412(13) 0.0624(10) 0.0384(11) 0.0238(9) 0.0165(9) 0.0133(9) C4 0.0415(14) 0.0682(11) 0.0276(10) 0.0126(8) 0.0126(8) 0.0198(10) C5 0.0367(13) 0.0628(10) 0.0243(10) -0.0027(7) 0.0029(8) 0.0178(9) C6 0.0295(11) 0.0427(8) 0.0248(9) 0.0032(6) 0.0036(7) 0.0130(8) C7 0.0526(16) 0.0443(8) 0.0527(13) 0.0048(8) 0.0205(10) -0.0150(9) C8 0.073(2) 0.1230(19) 0.0386(14) 0.0210(12) 0.0262(12) 0.0225(16) C9 0.0411(13) 0.0426(8) 0.0317(9) -0.0088(7) 0.0028(8) 0.0006(8) C31 0.0230(10) 0.0286(6) 0.0233(8) -0.0028(5) 0.0019(7) -0.0002(6) C32 0.0261(11) 0.0292(6) 0.0283(9) -0.0030(6) 0.0031(7) 0.0007(7) C33 0.0313(12) 0.0340(7) 0.0368(10) -0.0043(7) 0.0007(8) 0.0069(7) C34 0.0372(12) 0.0280(6) 0.0262(9) 0.0020(6) -0.0058(8) 0.0036(7) C35 0.0283(11) 0.0271(6) 0.0240(8) 0.0019(5) 0.0007(7) -0.0001(7) C36 0.0265(10) 0.0232(6) 0.0204(8) -0.0002(5) 0.0015(6) -0.0015(6) C41 0.0385(14) 0.0382(8) 0.0507(12) 0.0062(7) -0.0070(9) 0.0043(8) C42 0.0492(17) 0.0482(9) 0.0762(17) -0.0144(10) -0.0076(12) 0.0049(10) C43 0.0434(15) 0.0398(8) 0.0732(15) -0.0125(9) -0.0078(11) -0.0062(9) C44 0.0377(16) 0.0417(9) 0.117(2) -0.0147(11) -0.0206(15) -0.0062(9) C51 0.0380(14) 0.0481(9) 0.0647(14) -0.0075(9) 0.0240(10) -0.0022(9) C53 0.0507(19) 0.0997(16) 0.078(2) 0.0270(15) -0.0039(14) 0.0011(14) C54 0.0374(14) 0.0678(11) 0.0367(11) 0.0047(9) -0.0007(9) -0.0022(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 Li1 O1 1.988(2) . ? Li1 O2 1.989(3) . ? Li1 C31 2.371(2) . ? Li1 C36 2.385(3) . ? Li1 B1 2.473(3) . ? Li1 B1 2.474(4) 3_566 ? Li1 C31 2.514(4) 3_566 ? Li1 C36 2.516(3) 3_566 ? O1 C44 1.439(2) . ? O1 C41 1.451(2) . ? O2 C54 1.437(2) . ? O2 C51 1.439(3) . ? B1 C31 1.5085(19) . ? B1 C36 1.545(3) 3_566 ? B1 C1 1.624(3) . ? B1 Li1 2.474(4) 3_566 ? C1 C2 1.404(3) . ? C1 C6 1.412(2) . ? C2 C3 1.410(3) . ? C2 C7 1.489(2) . ? C3 C4 1.380(3) . ? C3 H3 0.9500 . ? C4 C5 1.369(3) . ? C4 C8 1.518(4) . ? C5 C6 1.404(3) . ? C5 H5 0.9500 . ? C6 C9 1.502(3) . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C31 C32 1.449(3) . ? C31 C36 1.480(3) . ? C31 Li1 2.514(4) 3_566 ? C32 C33 1.3468(19) . ? C32 H32 0.9500 . ? C33 C34 1.425(3) . ? C33 H33 0.9500 . ? C34 C35 1.366(3) . ? C34 H34 0.9500 . ? C35 C36 1.4197(16) . ? C35 H35 0.9500 . ? C36 B1 1.545(3) 3_566 ? C36 Li1 2.516(3) 3_566 ? C41 C42 1.474(2) . ? C41 H41A 0.9900 . ? C41 H41B 0.9900 . ? C42 C43 1.523(4) . ? C42 H42A 0.9900 . ? C42 H42B 0.9900 . ? C43 C44 1.460(3) . ? C43 H43A 0.9900 . ? C43 H43B 0.9900 . ? C44 H44A 0.9900 . ? C44 H44B 0.9900 . ? C51 C52' 1.354(6) . ? C51 C52 1.566(7) . ? C51 H51A 0.9900 . ? C51 H51B 0.9900 . ? C51 H51C 0.9900 . ? C51 H51D 0.9900 . ? C52 C53 1.402(8) . ? C52 H52A 0.9900 . ? C52 H52B 0.9900 . ? C52' C53 1.576(9) . ? C52' H52C 0.9900 . ? C52' H52D 0.9900 . ? C53 C54 1.481(4) . ? C53 H53A 0.9900 . ? C53 H53B 0.9900 . ? C53 H53C 0.9900 . ? C53 H53D 0.9900 . ? C54 H54A 0.9900 . ? C54 H54B 0.9900 . ? 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 Li1 O2 89.94(11) . . ? O1 Li1 C31 159.10(19) . . ? O2 Li1 C31 96.50(12) . . ? O1 Li1 C36 162.7(2) . . ? O2 Li1 C36 95.18(10) . . ? C31 Li1 C36 36.27(8) . . ? O1 Li1 B1 125.01(14) . . ? O2 Li1 B1 122.04(16) . . ? C31 Li1 B1 36.21(6) . . ? C36 Li1 B1 65.27(8) . . ? O1 Li1 B1 127.28(18) . 3_566 ? O2 Li1 B1 120.02(13) . 3_566 ? C31 Li1 B1 65.65(9) . 3_566 ? C36 Li1 B1 37.03(8) . 3_566 ? B1 Li1 B1 76.96(11) . 3_566 ? O1 Li1 C31 106.22(13) . 3_566 ? O2 Li1 C31 155.18(16) . 3_566 ? C31 Li1 C31 75.14(10) . 3_566 ? C36 Li1 C31 64.10(9) . 3_566 ? B1 Li1 C31 63.58(9) . 3_566 ? B1 Li1 C31 35.19(6) 3_566 3_566 ? O1 Li1 C36 104.74(10) . 3_566 ? O2 Li1 C36 158.11(16) . 3_566 ? C31 Li1 C36 64.25(7) . 3_566 ? C36 Li1 C36 75.62(8) . 3_566 ? B1 Li1 C36 36.07(7) . 3_566 ? B1 Li1 C36 63.36(9) 3_566 3_566 ? C31 Li1 C36 34.23(8) 3_566 3_566 ? C44 O1 C41 106.52(11) . . ? C44 O1 Li1 128.73(12) . . ? C41 O1 Li1 124.61(13) . . ? C54 O2 C51 107.97(17) . . ? C54 O2 Li1 127.31(19) . . ? C51 O2 Li1 124.56(16) . . ? C31 B1 C36 116.87(17) . 3_566 ? C31 B1 C1 123.62(16) . . ? C36 B1 C1 119.50(12) 3_566 . ? C31 B1 Li1 68.19(9) . . ? C36 B1 Li1 73.48(11) 3_566 . ? C1 B1 Li1 129.86(14) . . ? C31 B1 Li1 73.85(12) . 3_566 ? C36 B1 Li1 68.35(12) 3_566 3_566 ? C1 B1 Li1 127.04(11) . 3_566 ? Li1 B1 Li1 103.04(11) . 3_566 ? C2 C1 C6 116.90(18) . . ? C2 C1 B1 122.07(14) . . ? C6 C1 B1 121.02(16) . . ? C1 C2 C3 120.53(17) . . ? C1 C2 C7 121.99(19) . . ? C3 C2 C7 117.47(19) . . ? C4 C3 C2 121.9(2) . . ? C4 C3 H3 119.1 . . ? C2 C3 H3 119.1 . . ? C5 C4 C3 117.8(2) . . ? C5 C4 C8 121.2(2) . . ? C3 C4 C8 121.0(2) . . ? C4 C5 C6 122.12(17) . . ? C4 C5 H5 118.9 . . ? C6 C5 H5 118.9 . . ? C5 C6 C1 120.67(17) . . ? C5 C6 C9 117.53(15) . . ? C1 C6 C9 121.78(18) . . ? C2 C7 H7A 109.5 . . ? C2 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C2 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C4 C8 H8A 109.5 . . ? C4 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C4 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C6 C9 H9A 109.5 . . ? C6 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C6 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C32 C31 C36 115.45(12) . . ? C32 C31 B1 121.95(17) . . ? C36 C31 B1 122.56(16) . . ? C32 C31 Li1 123.08(13) . . ? C36 C31 Li1 72.38(12) . . ? B1 C31 Li1 75.60(10) . . ? C32 C31 Li1 131.87(10) . 3_566 ? C36 C31 Li1 72.97(12) . 3_566 ? B1 C31 Li1 70.95(12) . 3_566 ? Li1 C31 Li1 104.86(9) . 3_566 ? C33 C32 C31 123.97(19) . . ? C33 C32 H32 118.0 . . ? C31 C32 H32 118.0 . . ? C32 C33 C34 120.25(19) . . ? C32 C33 H33 119.9 . . ? C34 C33 H33 119.9 . . ? C35 C34 C33 118.69(13) . . ? C35 C34 H34 120.7 . . ? C33 C34 H34 120.7 . . ? C34 C35 C36 124.05(18) . . ? C34 C35 H35 118.0 . . ? C36 C35 H35 118.0 . . ? C35 C36 C31 117.55(16) . . ? C35 C36 B1 121.85(17) . 3_566 ? C31 C36 B1 120.57(12) . 3_566 ? C35 C36 Li1 124.25(11) . . ? C31 C36 Li1 71.35(11) . . ? B1 C36 Li1 74.63(12) 3_566 . ? C35 C36 Li1 131.28(11) . 3_566 ? C31 C36 Li1 72.81(11) . 3_566 ? B1 C36 Li1 70.45(11) 3_566 3_566 ? Li1 C36 Li1 104.38(8) . 3_566 ? O1 C41 C42 103.82(13) . . ? O1 C41 H41A 111.0 . . ? C42 C41 H41A 111.0 . . ? O1 C41 H41B 111.0 . . ? C42 C41 H41B 111.0 . . ? H41A C41 H41B 109.0 . . ? C41 C42 C43 103.8(2) . . ? C41 C42 H42A 111.0 . . ? C43 C42 H42A 111.0 . . ? C41 C42 H42B 111.0 . . ? C43 C42 H42B 111.0 . . ? H42A C42 H42B 109.0 . . ? C44 C43 C42 102.87(16) . . ? C44 C43 H43A 111.2 . . ? C42 C43 H43A 111.2 . . ? C44 C43 H43B 111.2 . . ? C42 C43 H43B 111.2 . . ? H43A C43 H43B 109.1 . . ? O1 C44 C43 109.62(18) . . ? O1 C44 H44A 109.7 . . ? C43 C44 H44A 109.7 . . ? O1 C44 H44B 109.7 . . ? C43 C44 H44B 109.7 . . ? H44A C44 H44B 108.2 . . ? C52' C51 O2 110.2(4) . . ? O2 C51 C52 100.9(4) . . ? C52' C51 H51A 131.3 . . ? O2 C51 H51A 111.6 . . ? C52 C51 H51A 111.6 . . ? C52' C51 H51B 76.4 . . ? O2 C51 H51B 111.6 . . ? C52 C51 H51B 111.6 . . ? H51A C51 H51B 109.4 . . ? C52' C51 H51C 109.6 . . ? O2 C51 H51C 109.6 . . ? C52 C51 H51C 141.7 . . ? H51A C51 H51C 78.4 . . ? C52' C51 H51D 109.6 . . ? O2 C51 H51D 109.6 . . ? C52 C51 H51D 81.7 . . ? H51C C51 H51D 108.1 . . ? C53 C52 C51 104.4(5) . . ? C53 C52 H52A 110.9 . . ? C51 C52 H52A 110.9 . . ? C53 C52 H52B 110.9 . . ? C51 C52 H52B 110.9 . . ? H52A C52 H52B 108.9 . . ? C51 C52' C53 106.2(6) . . ? C51 C52' H52C 110.5 . . ? C53 C52' H52C 110.5 . . ? C51 C52' H52D 110.5 . . ? C53 C52' H52D 110.5 . . ? H52C C52' H52D 108.7 . . ? C52 C53 C54 105.4(3) . . ? C54 C53 C52' 100.9(3) . . ? C52 C53 H53A 110.7 . . ? C54 C53 H53A 110.7 . . ? C52 C53 H53B 110.7 . . ? C54 C53 H53B 110.7 . . ? H53A C53 H53B 108.8 . . ? C54 C53 H53C 111.6 . . ? C52' C53 H53C 111.6 . . ? C52 C53 H53D 77.8 . . ? C54 C53 H53D 111.6 . . ? C52' C53 H53D 111.6 . . ? H53C C53 H53D 109.4 . . ? O2 C54 C53 107.8(2) . . ? O2 C54 H54A 110.2 . . ? C53 C54 H54A 110.2 . . ? O2 C54 H54B 110.2 . . ? C53 C54 H54B 110.2 . . ? H54A C54 H54B 108.5 . . ? 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 O2 Li1 O1 C44 -2.4(3) . . . . ? C31 Li1 O1 C44 -110.8(5) . . . . ? C36 Li1 O1 C44 105.1(5) . . . . ? B1 Li1 O1 C44 -132.7(3) . . . . ? B1 Li1 O1 C44 126.5(3) 3_566 . . . ? C31 Li1 O1 C44 158.5(2) 3_566 . . . ? C36 Li1 O1 C44 -166.0(2) 3_566 . . . ? O2 Li1 O1 C41 -177.36(19) . . . . ? C31 Li1 O1 C41 74.3(6) . . . . ? C36 Li1 O1 C41 -69.8(5) . . . . ? B1 Li1 O1 C41 52.3(3) . . . . ? B1 Li1 O1 C41 -48.5(3) 3_566 . . . ? C31 Li1 O1 C41 -16.5(3) 3_566 . . . ? C36 Li1 O1 C41 19.1(3) 3_566 . . . ? O1 Li1 O2 C54 96.20(19) . . . . ? C31 Li1 O2 C54 -103.72(18) . . . . ? C36 Li1 O2 C54 -67.28(19) . . . . ? B1 Li1 O2 C54 -131.26(19) . . . . ? B1 Li1 O2 C54 -38.1(2) 3_566 . . . ? C31 Li1 O2 C54 -35.4(4) 3_566 . . . ? C36 Li1 O2 C54 -131.0(4) 3_566 . . . ? O1 Li1 O2 C51 -89.02(18) . . . . ? C31 Li1 O2 C51 71.05(19) . . . . ? C36 Li1 O2 C51 107.50(17) . . . . ? B1 Li1 O2 C51 43.5(2) . . . . ? B1 Li1 O2 C51 136.63(17) 3_566 . . . ? C31 Li1 O2 C51 139.4(3) 3_566 . . . ? C36 Li1 O2 C51 43.8(5) 3_566 . . . ? O1 Li1 B1 C31 166.9(2) . . . . ? O2 Li1 B1 C31 51.04(18) . . . . ? C36 Li1 B1 C31 -29.12(12) . . . . ? B1 Li1 B1 C31 -66.41(11) 3_566 . . . ? C31 Li1 B1 C31 -101.17(13) 3_566 . . . ? C36 Li1 B1 C31 -128.79(18) 3_566 . . . ? O1 Li1 B1 C36 -64.3(2) . . . 3_566 ? O2 Li1 B1 C36 179.82(19) . . . 3_566 ? C31 Li1 B1 C36 128.79(18) . . . 3_566 ? C36 Li1 B1 C36 99.67(11) . . . 3_566 ? B1 Li1 B1 C36 62.37(11) 3_566 . . 3_566 ? C31 Li1 B1 C36 27.62(9) 3_566 . . 3_566 ? O1 Li1 B1 C1 50.7(3) . . . . ? O2 Li1 B1 C1 -65.3(2) . . . . ? C31 Li1 B1 C1 -116.3(2) . . . . ? C36 Li1 B1 C1 -145.41(15) . . . . ? B1 Li1 B1 C1 177.30(16) 3_566 . . . ? C31 Li1 B1 C1 142.54(14) 3_566 . . . ? C36 Li1 B1 C1 114.92(16) 3_566 . . . ? O1 Li1 B1 Li1 -126.6(2) . . . 3_566 ? O2 Li1 B1 Li1 117.45(18) . . . 3_566 ? C31 Li1 B1 Li1 66.41(11) . . . 3_566 ? C36 Li1 B1 Li1 37.29(7) . . . 3_566 ? B1 Li1 B1 Li1 0.001(1) 3_566 . . 3_566 ? C31 Li1 B1 Li1 -34.75(6) 3_566 . . 3_566 ? C36 Li1 B1 Li1 -62.37(11) 3_566 . . 3_566 ? C31 B1 C1 C2 -115.53(16) . . . . ? C36 B1 C1 C2 65.7(2) 3_566 . . . ? Li1 B1 C1 C2 -27.0(2) . . . . ? Li1 B1 C1 C2 149.69(14) 3_566 . . . ? C31 B1 C1 C6 65.8(2) . . . . ? C36 B1 C1 C6 -112.98(16) 3_566 . . . ? Li1 B1 C1 C6 154.35(15) . . . . ? Li1 B1 C1 C6 -29.0(2) 3_566 . . . ? C6 C1 C2 C3 2.9(2) . . . . ? B1 C1 C2 C3 -175.82(15) . . . . ? C6 C1 C2 C7 -176.20(17) . . . . ? B1 C1 C2 C7 5.1(3) . . . . ? C1 C2 C3 C4 -2.1(3) . . . . ? C7 C2 C3 C4 177.02(19) . . . . ? C2 C3 C4 C5 0.5(3) . . . . ? C2 C3 C4 C8 178.68(18) . . . . ? C3 C4 C5 C6 0.2(3) . . . . ? C8 C4 C5 C6 -178.01(18) . . . . ? C4 C5 C6 C1 0.7(3) . . . . ? C4 C5 C6 C9 179.16(17) . . . . ? C2 C1 C6 C5 -2.2(2) . . . . ? B1 C1 C6 C5 176.48(14) . . . . ? C2 C1 C6 C9 179.42(15) . . . . ? B1 C1 C6 C9 -1.9(2) . . . . ? C36 B1 C31 C32 -177.17(13) 3_566 . . . ? C1 B1 C31 C32 4.0(2) . . . . ? Li1 B1 C31 C32 -120.27(16) . . . . ? Li1 B1 C31 C32 128.09(14) 3_566 . . . ? C36 B1 C31 C36 0.8(2) 3_566 . . . ? C1 B1 C31 C36 -178.07(13) . . . . ? Li1 B1 C31 C36 57.67(14) . . . . ? Li1 B1 C31 C36 -53.97(13) 3_566 . . . ? C36 B1 C31 Li1 -56.90(15) 3_566 . . . ? C1 B1 C31 Li1 124.26(17) . . . . ? Li1 B1 C31 Li1 -111.64(9) 3_566 . . . ? C36 B1 C31 Li1 54.74(13) 3_566 . . 3_566 ? C1 B1 C31 Li1 -124.10(15) . . . 3_566 ? Li1 B1 C31 Li1 111.64(9) . . . 3_566 ? O1 Li1 C31 C32 87.8(5) . . . . ? O2 Li1 C31 C32 -19.4(2) . . . . ? C36 Li1 C31 C32 -109.35(16) . . . . ? B1 Li1 C31 C32 119.0(2) . . . . ? B1 Li1 C31 C32 -139.52(16) 3_566 . . . ? C31 Li1 C31 C32 -175.63(18) 3_566 . . . ? C36 Li1 C31 C32 149.63(16) 3_566 . . . ? O1 Li1 C31 C36 -162.9(5) . . . . ? O2 Li1 C31 C36 89.90(14) . . . . ? B1 Li1 C31 C36 -131.65(16) . . . . ? B1 Li1 C31 C36 -30.18(9) 3_566 . . . ? C31 Li1 C31 C36 -66.28(11) 3_566 . . . ? C36 Li1 C31 C36 -101.02(10) 3_566 . . . ? O1 Li1 C31 B1 -31.2(5) . . . . ? O2 Li1 C31 B1 -138.44(18) . . . . ? C36 Li1 C31 B1 131.65(16) . . . . ? B1 Li1 C31 B1 101.48(13) 3_566 . . . ? C31 Li1 C31 B1 65.37(11) 3_566 . . . ? C36 Li1 C31 B1 30.63(12) 3_566 . . . ? O1 Li1 C31 Li1 -96.6(5) . . . 3_566 ? O2 Li1 C31 Li1 156.18(17) . . . 3_566 ? C36 Li1 C31 Li1 66.28(11) . . . 3_566 ? B1 Li1 C31 Li1 -65.37(11) . . . 3_566 ? B1 Li1 C31 Li1 36.10(6) 3_566 . . 3_566 ? C31 Li1 C31 Li1 0.0 3_566 . . 3_566 ? C36 Li1 C31 Li1 -34.74(7) 3_566 . . 3_566 ? C36 C31 C32 C33 -0.2(2) . . . . ? B1 C31 C32 C33 177.87(13) . . . . ? Li1 C31 C32 C33 84.6(2) . . . . ? Li1 C31 C32 C33 -89.69(19) 3_566 . . . ? C31 C32 C33 C34 1.8(2) . . . . ? C32 C33 C34 C35 -2.4(2) . . . . ? C33 C34 C35 C36 1.5(2) . . . . ? C34 C35 C36 C31 0.1(2) . . . . ? C34 C35 C36 B1 -177.88(14) . . . 3_566 ? C34 C35 C36 Li1 -85.3(2) . . . . ? C34 C35 C36 Li1 90.9(3) . . . 3_566 ? C32 C31 C36 C35 -0.72(17) . . . . ? B1 C31 C36 C35 -178.78(12) . . . . ? Li1 C31 C36 C35 -119.60(13) . . . . ? Li1 C31 C36 C35 128.14(12) 3_566 . . . ? C32 C31 C36 B1 177.27(12) . . . 3_566 ? B1 C31 C36 B1 -0.8(2) . . . 3_566 ? Li1 C31 C36 B1 58.38(13) . . . 3_566 ? Li1 C31 C36 B1 -53.88(12) 3_566 . . 3_566 ? C32 C31 C36 Li1 118.89(13) . . . . ? B1 C31 C36 Li1 -59.17(13) . . . . ? Li1 C31 C36 Li1 -112.26(8) 3_566 . . . ? C32 C31 C36 Li1 -128.85(12) . . . 3_566 ? B1 C31 C36 Li1 53.09(13) . . . 3_566 ? Li1 C31 C36 Li1 112.26(8) . . . 3_566 ? O1 Li1 C36 C35 -89.5(5) . . . . ? O2 Li1 C36 C35 17.2(2) . . . . ? C31 Li1 C36 C35 111.1(2) . . . . ? B1 Li1 C36 C35 140.22(19) . . . . ? B1 Li1 C36 C35 -118.4(2) 3_566 . . . ? C31 Li1 C36 C35 -148.50(18) 3_566 . . . ? C36 Li1 C36 C35 177.0(2) 3_566 . . . ? O1 Li1 C36 C31 159.3(5) . . . . ? O2 Li1 C36 C31 -93.93(15) . . . . ? B1 Li1 C36 C31 29.07(9) . . . . ? B1 Li1 C36 C31 130.50(11) 3_566 . . . ? C31 Li1 C36 C31 100.36(10) 3_566 . . . ? C36 Li1 C36 C31 65.88(9) 3_566 . . . ? O1 Li1 C36 B1 28.8(4) . . . 3_566 ? O2 Li1 C36 B1 135.57(14) . . . 3_566 ? C31 Li1 C36 B1 -130.50(11) . . . 3_566 ? B1 Li1 C36 B1 -101.43(11) . . . 3_566 ? C31 Li1 C36 B1 -30.14(8) 3_566 . . 3_566 ? C36 Li1 C36 B1 -64.62(10) 3_566 . . 3_566 ? O1 Li1 C36 Li1 93.4(5) . . . 3_566 ? O2 Li1 C36 Li1 -159.82(18) . . . 3_566 ? C31 Li1 C36 Li1 -65.89(9) . . . 3_566 ? B1 Li1 C36 Li1 -36.81(8) . . . 3_566 ? B1 Li1 C36 Li1 64.61(10) 3_566 . . 3_566 ? C31 Li1 C36 Li1 34.47(7) 3_566 . . 3_566 ? C36 Li1 C36 Li1 0.0 3_566 . . 3_566 ? C44 O1 C41 C42 -30.5(3) . . . . ? Li1 O1 C41 C42 145.4(2) . . . . ? O1 C41 C42 C43 36.9(3) . . . . ? C41 C42 C43 C44 -29.3(3) . . . . ? C41 O1 C44 C43 11.9(3) . . . . ? Li1 O1 C44 C43 -163.8(2) . . . . ? C42 C43 C44 O1 11.0(3) . . . . ? C54 O2 C51 C52' 7.8(4) . . . . ? Li1 O2 C51 C52' -167.8(4) . . . . ? C54 O2 C51 C52 -27.9(3) . . . . ? Li1 O2 C51 C52 156.4(3) . . . . ? C52' C51 C52 C53 -72.5(8) . . . . ? O2 C51 C52 C53 37.1(5) . . . . ? O2 C51 C52' C53 -21.5(6) . . . . ? C52 C51 C52' C53 58.8(7) . . . . ? C51 C52 C53 C54 -31.2(5) . . . . ? C51 C52 C53 C52' 55.9(6) . . . . ? C51 C52' C53 C52 -75.0(7) . . . . ? C51 C52' C53 C54 26.4(6) . . . . ? C51 O2 C54 C53 10.4(2) . . . . ? Li1 O2 C54 C53 -174.15(16) . . . . ? C52 C53 C54 O2 14.4(4) . . . . ? C52' C53 C54 O2 -21.5(4) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.568 _refine_diff_density_min -0.418 _refine_diff_density_rms 0.048 _database_code_depnum_ccdc_archive 'CCDC 922260' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_global data_wa1027 #TrackingRef 'deposit.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C38 H50 B2 Li2 O2' _chemical_formula_sum 'C38 H50 B2 Li2 O2' _chemical_formula_weight 574.28 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 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' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Li Li -0.0003 0.0001 '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 C2/c _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 20.2695(12) _cell_length_b 13.5626(9) _cell_length_c 14.2131(8) _cell_angle_alpha 90.00 _cell_angle_beta 117.614(4) _cell_angle_gamma 90.00 _cell_volume 3462.2(4) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 15811 _cell_measurement_theta_min 3.3 _cell_measurement_theta_max 26.0 _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_max 0.37 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.33 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.102 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1240 _exptl_absorpt_coefficient_mu 0.064 _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 'STOE IPDS II two-circle-diffractometer' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 18192 _diffrn_reflns_av_R_equivalents 0.0836 _diffrn_reflns_av_sigmaI/netI 0.0435 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.24 _diffrn_reflns_theta_max 25.62 _reflns_number_total 3242 _reflns_number_gt 2679 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'X-Area (Stoe & Cie, 2001)' _computing_cell_refinement 'X-Area (Stoe & Cie, 2001)' _computing_data_reduction 'X-Area (Stoe & Cie, 2001)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008) ' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008) ' _computing_molecular_graphics 'XP (Sheldrick, 2008)' _computing_publication_material SHELXL97 _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^)+(0.0775P)^2^+0.6605P] 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 3242 _refine_ls_number_parameters 202 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0556 _refine_ls_R_factor_gt 0.0448 _refine_ls_wR_factor_ref 0.1246 _refine_ls_wR_factor_gt 0.1184 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.046 _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 Li1 Li 0.77057(12) 0.12504(16) 0.52352(17) 0.0284(5) Uani 1 1 d . . . O1 O 0.79742(5) -0.01205(7) 0.55284(8) 0.0335(3) Uani 1 1 d . . . B1 B 0.81982(7) 0.26513(10) 0.48405(11) 0.0209(3) Uani 1 1 d . . . C1 C 0.89084(7) 0.28016(9) 0.46390(9) 0.0216(3) Uani 1 1 d . . . C2 C 0.93809(7) 0.20068(9) 0.47182(10) 0.0254(3) Uani 1 1 d . . . C3 C 0.99575(7) 0.21273(10) 0.44506(11) 0.0290(3) Uani 1 1 d . . . H3 H 1.0262 0.1577 0.4500 0.035 Uiso 1 1 calc R . . C4 C 1.00986(7) 0.30243(11) 0.41158(10) 0.0287(3) Uani 1 1 d . . . C5 C 0.96546(7) 0.38174(10) 0.40727(10) 0.0304(3) Uani 1 1 d . . . H5 H 0.9750 0.4445 0.3864 0.036 Uiso 1 1 calc R . . C6 C 0.90704(7) 0.37172(10) 0.43293(10) 0.0260(3) Uani 1 1 d . . . C7 C 0.92785(9) 0.10188(10) 0.51153(14) 0.0410(4) Uani 1 1 d . . . H7A H 0.9665 0.0564 0.5151 0.062 Uiso 1 1 calc R . . H7B H 0.8787 0.0754 0.4629 0.062 Uiso 1 1 calc R . . H7C H 0.9316 0.1095 0.5824 0.062 Uiso 1 1 calc R . . C8 C 1.07230(8) 0.31427(13) 0.38248(12) 0.0380(4) Uani 1 1 d . . . H8A H 1.1202 0.3050 0.4459 0.057 Uiso 1 1 calc R . . H8B H 1.0703 0.3805 0.3537 0.057 Uiso 1 1 calc R . . H8C H 1.0669 0.2650 0.3290 0.057 Uiso 1 1 calc R . . C9 C 0.86195(9) 0.46177(11) 0.42800(14) 0.0399(4) Uani 1 1 d . . . H9A H 0.8822 0.5193 0.4084 0.060 Uiso 1 1 calc R . . H9B H 0.8643 0.4729 0.4976 0.060 Uiso 1 1 calc R . . H9C H 0.8100 0.4517 0.3748 0.060 Uiso 1 1 calc R . . C31 C 0.74355(6) 0.24001(8) 0.39145(9) 0.0201(3) Uani 1 1 d . . . C32 C 0.73352(7) 0.23069(9) 0.28452(10) 0.0247(3) Uani 1 1 d . . . H32 H 0.7755 0.2398 0.2725 0.030 Uiso 1 1 calc R . . C33 C 0.66679(8) 0.20950(10) 0.20014(10) 0.0305(3) Uani 1 1 d . . . H33 H 0.6629 0.2050 0.1310 0.037 Uiso 1 1 calc R . . C34 C 0.60278(8) 0.19401(11) 0.21496(10) 0.0311(3) Uani 1 1 d . . . H34 H 0.5563 0.1785 0.1560 0.037 Uiso 1 1 calc R . . C35 C 0.60836(7) 0.20148(10) 0.31373(10) 0.0262(3) Uani 1 1 d . . . H35 H 0.5650 0.1906 0.3220 0.031 Uiso 1 1 calc R . . C36 C 0.67706(6) 0.22511(9) 0.40650(9) 0.0206(3) Uani 1 1 d . . . C41 C 0.87002(12) 0.02628(15) 0.73740(14) 0.0577(5) Uani 1 1 d . . . H41A H 0.9033 -0.0023 0.8067 0.087 Uiso 1 1 calc R . . H41B H 0.8262 0.0543 0.7396 0.087 Uiso 1 1 calc R . . H41C H 0.8963 0.0783 0.7203 0.087 Uiso 1 1 calc R . . C42 C 0.84615(11) -0.05171(13) 0.65491(15) 0.0567(5) Uani 1 1 d . . . H42A H 0.8905 -0.0807 0.6533 0.068 Uiso 1 1 calc R . . H42B H 0.8203 -0.1048 0.6727 0.068 Uiso 1 1 calc R . . C43 C 0.77363(10) -0.08431(11) 0.46947(15) 0.0489(4) Uani 1 1 d . . . H43A H 0.7479 -0.1390 0.4852 0.059 Uiso 1 1 calc R . . H43B H 0.8176 -0.1119 0.4658 0.059 Uiso 1 1 calc R . . C44 C 0.72261(10) -0.03911(12) 0.36597(14) 0.0471(4) Uani 1 1 d . . . H44A H 0.7069 -0.0892 0.3100 0.071 Uiso 1 1 calc R . . H44B H 0.7484 0.0144 0.3501 0.071 Uiso 1 1 calc R . . H44C H 0.6788 -0.0126 0.3694 0.071 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 Li1 0.0284(11) 0.0265(10) 0.0321(11) 0.0020(9) 0.0155(10) 0.0036(9) O1 0.0344(5) 0.0265(5) 0.0444(6) 0.0055(4) 0.0225(5) 0.0056(4) B1 0.0191(6) 0.0222(6) 0.0228(7) 0.0014(5) 0.0110(5) 0.0022(5) C1 0.0169(6) 0.0301(6) 0.0172(6) -0.0020(5) 0.0074(5) -0.0004(5) C2 0.0202(6) 0.0306(7) 0.0267(6) -0.0032(5) 0.0120(5) 0.0000(5) C3 0.0216(6) 0.0368(7) 0.0326(7) -0.0045(5) 0.0160(6) 0.0020(5) C4 0.0206(6) 0.0451(8) 0.0230(6) -0.0031(5) 0.0124(5) -0.0026(5) C5 0.0276(7) 0.0361(7) 0.0310(7) 0.0048(6) 0.0166(6) -0.0011(5) C6 0.0219(6) 0.0325(7) 0.0257(6) 0.0026(5) 0.0129(5) 0.0012(5) C7 0.0394(8) 0.0295(7) 0.0696(11) 0.0047(7) 0.0383(8) 0.0074(6) C8 0.0273(7) 0.0565(9) 0.0383(8) 0.0001(7) 0.0220(7) -0.0020(6) C9 0.0401(8) 0.0326(7) 0.0589(10) 0.0124(7) 0.0332(8) 0.0066(6) C31 0.0198(6) 0.0210(6) 0.0212(6) 0.0002(4) 0.0108(5) 0.0017(4) C32 0.0244(6) 0.0289(6) 0.0233(6) -0.0008(5) 0.0132(5) -0.0002(5) C33 0.0317(7) 0.0403(8) 0.0202(6) -0.0040(5) 0.0125(6) -0.0026(6) C34 0.0232(7) 0.0421(8) 0.0219(6) -0.0038(5) 0.0053(5) -0.0031(5) C35 0.0184(6) 0.0340(7) 0.0244(6) -0.0021(5) 0.0085(5) -0.0011(5) C36 0.0174(6) 0.0220(6) 0.0217(6) -0.0001(5) 0.0086(5) 0.0016(4) C41 0.0597(11) 0.0692(12) 0.0408(9) 0.0162(9) 0.0204(8) 0.0169(9) C42 0.0573(11) 0.0415(9) 0.0601(11) 0.0204(8) 0.0177(9) 0.0130(8) C43 0.0451(9) 0.0280(7) 0.0737(12) -0.0094(7) 0.0277(9) -0.0014(6) C44 0.0503(10) 0.0437(9) 0.0530(10) -0.0152(7) 0.0289(8) -0.0113(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 Li1 O1 1.928(2) . ? Li1 C31 2.283(2) 7_656 ? Li1 C36 2.295(2) 7_656 ? Li1 C36 2.298(2) . ? Li1 C31 2.303(2) . ? Li1 B1 2.325(2) 7_656 ? Li1 B1 2.333(3) . ? Li1 Li1 3.481(4) 7_656 ? O1 C42 1.429(2) . ? O1 C43 1.438(2) . ? B1 C36 1.5330(17) 7_656 ? B1 C31 1.5337(18) . ? B1 C1 1.6055(17) . ? B1 Li1 2.325(2) 7_656 ? C1 C6 1.4062(18) . ? C1 C2 1.4114(17) . ? C2 C3 1.3961(17) . ? C2 C7 1.5053(19) . ? C3 C4 1.384(2) . ? C3 H3 0.9500 . ? C4 C5 1.385(2) . ? C4 C8 1.5114(17) . ? C5 C6 1.3979(17) . ? C5 H5 0.9500 . ? C6 C9 1.5074(19) . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C31 C32 1.4425(16) . ? C31 C36 1.4733(16) . ? C31 Li1 2.283(2) 7_656 ? C32 C33 1.3588(19) . ? C32 H32 0.9500 . ? C33 C34 1.4231(19) . ? C33 H33 0.9500 . ? C34 C35 1.3589(19) . ? C34 H34 0.9500 . ? C35 C36 1.4417(17) . ? C35 H35 0.9500 . ? C36 B1 1.5331(17) 7_656 ? C36 Li1 2.295(2) 7_656 ? C41 C42 1.484(3) . ? C41 H41A 0.9800 . ? C41 H41B 0.9800 . ? C41 H41C 0.9800 . ? C42 H42A 0.9900 . ? C42 H42B 0.9900 . ? C43 C44 1.483(3) . ? C43 H43A 0.9900 . ? C43 H43B 0.9900 . ? C44 H44A 0.9800 . ? C44 H44B 0.9800 . ? C44 H44C 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 Li1 C31 138.66(12) . 7_656 ? O1 Li1 C36 137.13(12) . 7_656 ? C31 Li1 C36 37.54(5) 7_656 7_656 ? O1 Li1 C36 141.42(12) . . ? C31 Li1 C36 69.26(7) 7_656 . ? C36 Li1 C36 81.45(8) 7_656 . ? O1 Li1 C31 140.00(12) . . ? C31 Li1 C31 81.25(8) 7_656 . ? C36 Li1 C31 68.97(7) 7_656 . ? C36 Li1 C31 37.36(5) . . ? O1 Li1 B1 139.94(12) . 7_656 ? C31 Li1 B1 38.86(6) 7_656 7_656 ? C36 Li1 B1 69.45(7) 7_656 7_656 ? C36 Li1 B1 38.73(5) . 7_656 ? C31 Li1 B1 69.14(7) . 7_656 ? O1 Li1 B1 136.74(11) . . ? C31 Li1 B1 69.33(7) 7_656 . ? C36 Li1 B1 38.68(6) 7_656 . ? C36 Li1 B1 69.28(7) . . ? C31 Li1 B1 38.64(6) . . ? B1 Li1 B1 83.28(8) 7_656 . ? O1 Li1 Li1 177.76(15) . 7_656 ? C31 Li1 Li1 40.83(5) 7_656 7_656 ? C36 Li1 Li1 40.75(6) 7_656 7_656 ? C36 Li1 Li1 40.70(5) . 7_656 ? C31 Li1 Li1 40.42(5) . 7_656 ? B1 Li1 Li1 41.73(6) 7_656 7_656 ? B1 Li1 Li1 41.55(6) . 7_656 ? C42 O1 C43 112.96(12) . . ? C42 O1 Li1 125.14(12) . . ? C43 O1 Li1 121.74(11) . . ? C36 B1 C31 116.17(10) 7_656 . ? C36 B1 C1 123.46(11) 7_656 . ? C31 B1 C1 120.37(10) . . ? C36 B1 Li1 69.67(8) 7_656 7_656 ? C31 B1 Li1 69.10(9) . 7_656 ? C1 B1 Li1 131.52(10) . 7_656 ? C36 B1 Li1 69.34(8) 7_656 . ? C31 B1 Li1 69.62(9) . . ? C1 B1 Li1 131.71(10) . . ? Li1 B1 Li1 96.72(8) 7_656 . ? C6 C1 C2 116.81(11) . . ? C6 C1 B1 121.78(10) . . ? C2 C1 B1 121.35(11) . . ? C3 C2 C1 120.78(12) . . ? C3 C2 C7 118.99(11) . . ? C1 C2 C7 120.22(11) . . ? C4 C3 C2 121.95(12) . . ? C4 C3 H3 119.0 . . ? C2 C3 H3 119.0 . . ? C3 C4 C5 117.66(11) . . ? C3 C4 C8 121.35(13) . . ? C5 C4 C8 120.97(13) . . ? C4 C5 C6 121.63(12) . . ? C4 C5 H5 119.2 . . ? C6 C5 H5 119.2 . . ? C5 C6 C1 121.09(12) . . ? C5 C6 C9 118.53(12) . . ? C1 C6 C9 120.37(11) . . ? C2 C7 H7A 109.5 . . ? C2 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C2 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C4 C8 H8A 109.5 . . ? C4 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C4 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C6 C9 H9A 109.5 . . ? C6 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C6 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C32 C31 C36 116.70(10) . . ? C32 C31 B1 121.16(10) . . ? C36 C31 B1 122.14(10) . . ? C32 C31 Li1 129.56(10) . 7_656 ? C36 C31 Li1 71.67(8) . 7_656 ? B1 C31 Li1 72.03(9) . 7_656 ? C32 C31 Li1 131.59(10) . . ? C36 C31 Li1 71.14(8) . . ? B1 C31 Li1 71.74(9) . . ? Li1 C31 Li1 98.75(8) 7_656 . ? C33 C32 C31 123.02(11) . . ? C33 C32 H32 118.5 . . ? C31 C32 H32 118.5 . . ? C32 C33 C34 120.23(12) . . ? C32 C33 H33 119.9 . . ? C34 C33 H33 119.9 . . ? C35 C34 C33 119.80(12) . . ? C35 C34 H34 120.1 . . ? C33 C34 H34 120.1 . . ? C34 C35 C36 122.96(12) . . ? C34 C35 H35 118.5 . . ? C36 C35 H35 118.5 . . ? C35 C36 C31 117.29(10) . . ? C35 C36 B1 121.02(10) . 7_656 ? C31 C36 B1 121.69(10) . 7_656 ? C35 C36 Li1 130.53(10) . 7_656 ? C31 C36 Li1 70.79(8) . 7_656 ? B1 C36 Li1 71.98(8) 7_656 7_656 ? C35 C36 Li1 130.83(10) . . ? C31 C36 Li1 71.51(8) . . ? B1 C36 Li1 71.60(8) 7_656 . ? Li1 C36 Li1 98.55(8) 7_656 . ? C42 C41 H41A 109.5 . . ? C42 C41 H41B 109.5 . . ? H41A C41 H41B 109.5 . . ? C42 C41 H41C 109.5 . . ? H41A C41 H41C 109.5 . . ? H41B C41 H41C 109.5 . . ? O1 C42 C41 110.65(14) . . ? O1 C42 H42A 109.5 . . ? C41 C42 H42A 109.5 . . ? O1 C42 H42B 109.5 . . ? C41 C42 H42B 109.5 . . ? H42A C42 H42B 108.1 . . ? O1 C43 C44 110.43(13) . . ? O1 C43 H43A 109.6 . . ? C44 C43 H43A 109.6 . . ? O1 C43 H43B 109.6 . . ? C44 C43 H43B 109.6 . . ? H43A C43 H43B 108.1 . . ? C43 C44 H44A 109.5 . . ? C43 C44 H44B 109.5 . . ? H44A C44 H44B 109.5 . . ? C43 C44 H44C 109.5 . . ? H44A C44 H44C 109.5 . . ? H44B C44 H44C 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 C31 Li1 O1 C42 -29.4(2) 7_656 . . . ? C36 Li1 O1 C42 27.9(2) 7_656 . . . ? C36 Li1 O1 C42 -153.81(18) . . . . ? C31 Li1 O1 C42 145.47(18) . . . . ? B1 Li1 O1 C42 -90.7(2) 7_656 . . . ? B1 Li1 O1 C42 85.9(2) . . . . ? C31 Li1 O1 C43 155.50(16) 7_656 . . . ? C36 Li1 O1 C43 -147.18(15) 7_656 . . . ? C36 Li1 O1 C43 31.1(2) . . . . ? C31 Li1 O1 C43 -29.6(2) . . . . ? B1 Li1 O1 C43 94.2(2) 7_656 . . . ? B1 Li1 O1 C43 -89.15(19) . . . . ? O1 Li1 B1 C36 -112.57(18) . . . 7_656 ? C31 Li1 B1 C36 27.79(7) 7_656 . . 7_656 ? C36 Li1 B1 C36 102.60(8) . . . 7_656 ? C31 Li1 B1 C36 130.00(10) . . . 7_656 ? B1 Li1 B1 C36 65.27(7) 7_656 . . 7_656 ? Li1 Li1 B1 C36 65.27(7) 7_656 . . 7_656 ? O1 Li1 B1 C31 117.43(18) . . . . ? C31 Li1 B1 C31 -102.21(8) 7_656 . . . ? C36 Li1 B1 C31 -130.00(10) 7_656 . . . ? C36 Li1 B1 C31 -27.40(7) . . . . ? B1 Li1 B1 C31 -64.73(8) 7_656 . . . ? Li1 Li1 B1 C31 -64.73(8) 7_656 . . . ? O1 Li1 B1 C1 4.4(2) . . . . ? C31 Li1 B1 C1 144.74(12) 7_656 . . . ? C36 Li1 B1 C1 116.95(15) 7_656 . . . ? C36 Li1 B1 C1 -140.45(12) . . . . ? C31 Li1 B1 C1 -113.05(14) . . . . ? B1 Li1 B1 C1 -177.78(14) 7_656 . . . ? Li1 Li1 B1 C1 -177.77(14) 7_656 . . . ? O1 Li1 B1 Li1 -177.8(2) . . . 7_656 ? C31 Li1 B1 Li1 -37.49(5) 7_656 . . 7_656 ? C36 Li1 B1 Li1 -65.27(7) 7_656 . . 7_656 ? C36 Li1 B1 Li1 37.32(5) . . . 7_656 ? C31 Li1 B1 Li1 64.73(8) . . . 7_656 ? B1 Li1 B1 Li1 0.0 7_656 . . 7_656 ? C36 B1 C1 C6 -93.66(15) 7_656 . . . ? C31 B1 C1 C6 86.10(15) . . . . ? Li1 B1 C1 C6 -1.99(19) 7_656 . . . ? Li1 B1 C1 C6 175.05(12) . . . . ? C36 B1 C1 C2 89.27(15) 7_656 . . . ? C31 B1 C1 C2 -90.98(15) . . . . ? Li1 B1 C1 C2 -179.07(12) 7_656 . . . ? Li1 B1 C1 C2 -2.03(19) . . . . ? C6 C1 C2 C3 -2.89(18) . . . . ? B1 C1 C2 C3 174.32(11) . . . . ? C6 C1 C2 C7 175.87(12) . . . . ? B1 C1 C2 C7 -6.91(18) . . . . ? C1 C2 C3 C4 1.1(2) . . . . ? C7 C2 C3 C4 -177.73(13) . . . . ? C2 C3 C4 C5 1.3(2) . . . . ? C2 C3 C4 C8 -179.77(12) . . . . ? C3 C4 C5 C6 -1.7(2) . . . . ? C8 C4 C5 C6 179.36(12) . . . . ? C4 C5 C6 C1 -0.2(2) . . . . ? C4 C5 C6 C9 179.06(13) . . . . ? C2 C1 C6 C5 2.50(18) . . . . ? B1 C1 C6 C5 -174.71(11) . . . . ? C2 C1 C6 C9 -176.78(12) . . . . ? B1 C1 C6 C9 6.02(19) . . . . ? C36 B1 C31 C32 178.89(10) 7_656 . . . ? C1 B1 C31 C32 -0.88(17) . . . . ? Li1 B1 C31 C32 125.89(12) 7_656 . . . ? Li1 B1 C31 C32 -128.12(12) . . . . ? C36 B1 C31 C36 -0.55(18) 7_656 . . . ? C1 B1 C31 C36 179.68(10) . . . . ? Li1 B1 C31 C36 -53.54(11) 7_656 . . . ? Li1 B1 C31 C36 52.45(11) . . . . ? C36 B1 C31 Li1 52.99(11) 7_656 . . 7_656 ? C1 B1 C31 Li1 -126.78(12) . . . 7_656 ? Li1 B1 C31 Li1 105.99(8) . . . 7_656 ? C36 B1 C31 Li1 -53.00(11) 7_656 . . . ? C1 B1 C31 Li1 127.23(12) . . . . ? Li1 B1 C31 Li1 -105.99(8) 7_656 . . . ? O1 Li1 C31 C32 6.9(3) . . . . ? C31 Li1 C31 C32 -176.48(14) 7_656 . . . ? C36 Li1 C31 C32 146.68(12) 7_656 . . . ? C36 Li1 C31 C32 -109.36(14) . . . . ? B1 Li1 C31 C32 -138.14(13) 7_656 . . . ? B1 Li1 C31 C32 115.82(14) . . . . ? Li1 Li1 C31 C32 -176.48(14) 7_656 . . . ? O1 Li1 C31 C36 116.30(19) . . . . ? C31 Li1 C31 C36 -67.11(8) 7_656 . . . ? C36 Li1 C31 C36 -103.95(8) 7_656 . . . ? B1 Li1 C31 C36 -28.78(7) 7_656 . . . ? B1 Li1 C31 C36 -134.81(10) . . . . ? Li1 Li1 C31 C36 -67.12(8) 7_656 . . . ? O1 Li1 C31 B1 -108.89(19) . . . . ? C31 Li1 C31 B1 67.70(8) 7_656 . . . ? C36 Li1 C31 B1 30.86(7) 7_656 . . . ? C36 Li1 C31 B1 134.81(10) . . . . ? B1 Li1 C31 B1 106.03(8) 7_656 . . . ? Li1 Li1 C31 B1 67.70(8) 7_656 . . . ? O1 Li1 C31 Li1 -176.6(2) . . . 7_656 ? C31 Li1 C31 Li1 0.0 7_656 . . 7_656 ? C36 Li1 C31 Li1 -36.84(5) 7_656 . . 7_656 ? C36 Li1 C31 Li1 67.12(8) . . . 7_656 ? B1 Li1 C31 Li1 38.34(5) 7_656 . . 7_656 ? B1 Li1 C31 Li1 -67.70(8) . . . 7_656 ? C36 C31 C32 C33 0.13(18) . . . . ? B1 C31 C32 C33 -179.33(12) . . . . ? Li1 C31 C32 C33 -87.51(17) 7_656 . . . ? Li1 C31 C32 C33 87.98(17) . . . . ? C31 C32 C33 C34 -0.9(2) . . . . ? C32 C33 C34 C35 0.7(2) . . . . ? C33 C34 C35 C36 0.2(2) . . . . ? C34 C35 C36 C31 -0.92(19) . . . . ? C34 C35 C36 B1 178.69(13) . . . 7_656 ? C34 C35 C36 Li1 86.44(17) . . . 7_656 ? C34 C35 C36 Li1 -89.44(17) . . . . ? C32 C31 C36 C35 0.73(16) . . . . ? B1 C31 C36 C35 -179.81(11) . . . . ? Li1 C31 C36 C35 126.48(12) 7_656 . . . ? Li1 C31 C36 C35 -127.10(12) . . . . ? C32 C31 C36 B1 -178.88(11) . . . 7_656 ? B1 C31 C36 B1 0.58(19) . . . 7_656 ? Li1 C31 C36 B1 -53.12(11) 7_656 . . 7_656 ? Li1 C31 C36 B1 53.29(11) . . . 7_656 ? C32 C31 C36 Li1 -125.76(12) . . . 7_656 ? B1 C31 C36 Li1 53.70(12) . . . 7_656 ? Li1 C31 C36 Li1 106.42(7) . . . 7_656 ? C32 C31 C36 Li1 127.83(12) . . . . ? B1 C31 C36 Li1 -52.71(12) . . . . ? Li1 C31 C36 Li1 -106.42(7) 7_656 . . . ? O1 Li1 C36 C35 -2.0(3) . . . . ? C31 Li1 C36 C35 -146.34(12) 7_656 . . . ? C36 Li1 C36 C35 176.83(13) 7_656 . . . ? C31 Li1 C36 C35 110.48(14) . . . . ? B1 Li1 C36 C35 -115.49(14) 7_656 . . . ? B1 Li1 C36 C35 138.75(12) . . . . ? Li1 Li1 C36 C35 176.83(13) 7_656 . . . ? O1 Li1 C36 C31 -112.47(19) . . . . ? C31 Li1 C36 C31 103.18(8) 7_656 . . . ? C36 Li1 C36 C31 66.35(7) 7_656 . . . ? B1 Li1 C36 C31 134.03(11) 7_656 . . . ? B1 Li1 C36 C31 28.27(7) . . . . ? Li1 Li1 C36 C31 66.35(7) 7_656 . . . ? O1 Li1 C36 B1 113.49(19) . . . 7_656 ? C31 Li1 C36 B1 -30.85(7) 7_656 . . 7_656 ? C36 Li1 C36 B1 -67.68(8) 7_656 . . 7_656 ? C31 Li1 C36 B1 -134.03(11) . . . 7_656 ? B1 Li1 C36 B1 -105.76(8) . . . 7_656 ? Li1 Li1 C36 B1 -67.68(8) 7_656 . . 7_656 ? O1 Li1 C36 Li1 -178.8(2) . . . 7_656 ? C31 Li1 C36 Li1 36.83(5) 7_656 . . 7_656 ? C36 Li1 C36 Li1 0.001(1) 7_656 . . 7_656 ? C31 Li1 C36 Li1 -66.35(7) . . . 7_656 ? B1 Li1 C36 Li1 67.68(8) 7_656 . . 7_656 ? B1 Li1 C36 Li1 -38.08(5) . . . 7_656 ? C43 O1 C42 C41 178.94(15) . . . . ? Li1 O1 C42 C41 3.5(2) . . . . ? C42 O1 C43 C44 179.32(14) . . . . ? Li1 O1 C43 C44 -5.04(19) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.190 _refine_diff_density_min -0.226 _refine_diff_density_rms 0.045 _database_code_depnum_ccdc_archive 'CCDC 922261' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_global data_wa1004 #TrackingRef 'deposit.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C34 H26 B2, 2(C6 H6)' _chemical_formula_sum 'C46 H38 B2' _chemical_formula_weight 612.38 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 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' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/c _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 9.2654(6) _cell_length_b 20.7217(10) _cell_length_c 9.6220(6) _cell_angle_alpha 90.00 _cell_angle_beta 109.597(5) _cell_angle_gamma 90.00 _cell_volume 1740.36(18) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 21483 _cell_measurement_theta_min 3.3 _cell_measurement_theta_max 26.0 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.33 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.169 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 648 _exptl_absorpt_coefficient_mu 0.065 _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 'STOE IPDS II two-circle-diffractometer' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 28271 _diffrn_reflns_av_R_equivalents 0.0596 _diffrn_reflns_av_sigmaI/netI 0.0273 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.29 _diffrn_reflns_theta_max 25.65 _reflns_number_total 3276 _reflns_number_gt 2677 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'X-Area (Stoe & Cie, 2001)' _computing_cell_refinement 'X-Area (Stoe & Cie, 2001)' _computing_data_reduction 'X-Area (Stoe & Cie, 2001)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008) ' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008) ' _computing_molecular_graphics 'XP in SHELXTL-Plus (Sheldrick, 1991)' _computing_publication_material SHELXL97 _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^)+(0.0660P)^2^+0.1806P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.017(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3276 _refine_ls_number_parameters 219 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0570 _refine_ls_R_factor_gt 0.0435 _refine_ls_wR_factor_ref 0.1144 _refine_ls_wR_factor_gt 0.1075 _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_restrained_S_all 1.027 _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 B1 B 0.56601(16) 0.55239(7) 0.93208(16) 0.0310(3) Uani 1 1 d . . . C1 C 0.63330(15) 0.60862(6) 0.86102(13) 0.0319(3) Uani 1 1 d . . . C2 C 0.56390(15) 0.66851(6) 0.83791(15) 0.0364(3) Uani 1 1 d . . . C3 C 0.62398(18) 0.71838(7) 0.77203(17) 0.0452(4) Uani 1 1 d . . . H3 H 0.5759 0.7595 0.7563 0.054 Uiso 1 1 calc R . . C4 C 0.74961(17) 0.70833(7) 0.73089(17) 0.0455(4) Uani 1 1 d . . . H4 H 0.7862 0.7424 0.6856 0.055 Uiso 1 1 calc R . . C5 C 0.82616(15) 0.64834(7) 0.75433(14) 0.0378(3) Uani 1 1 d . . . C6 C 0.76583(14) 0.59773(7) 0.81913(13) 0.0329(3) Uani 1 1 d . . . C7 C 0.42473(17) 0.68214(7) 0.88123(18) 0.0457(4) Uani 1 1 d . . . H7A H 0.3672 0.6421 0.8770 0.069 Uiso 1 1 calc R . . H7B H 0.3594 0.7138 0.8130 0.069 Uiso 1 1 calc R . . H7C H 0.4572 0.6994 0.9818 0.069 Uiso 1 1 calc R . . C21 C 0.95805(16) 0.63611(8) 0.71534(16) 0.0455(4) Uani 1 1 d . . . H21 H 0.9996 0.6697 0.6733 0.055 Uiso 1 1 calc R . . C22 C 1.02625(16) 0.57716(9) 0.73698(16) 0.0493(4) Uani 1 1 d . . . H22 H 1.1146 0.5700 0.7100 0.059 Uiso 1 1 calc R . . C23 C 0.96659(17) 0.52649(8) 0.79936(16) 0.0471(4) Uani 1 1 d . . . H23 H 1.0139 0.4852 0.8134 0.056 Uiso 1 1 calc R . . C24 C 0.84016(15) 0.53707(7) 0.83957(14) 0.0384(3) Uani 1 1 d . . . H24 H 0.8013 0.5028 0.8823 0.046 Uiso 1 1 calc R . . C31 C 0.61281(14) 0.54650(6) 1.10346(14) 0.0311(3) Uani 1 1 d . . . C32 C 0.71593(16) 0.58983(7) 1.19645(15) 0.0408(3) Uani 1 1 d . . . H32 H 0.7590 0.6230 1.1545 0.049 Uiso 1 1 calc R . . C33 C 0.75715(19) 0.58571(8) 1.34877(16) 0.0493(4) Uani 1 1 d . . . H33 H 0.8278 0.6158 1.4097 0.059 Uiso 1 1 calc R . . C34 C 0.69539(17) 0.53785(8) 1.41170(15) 0.0453(4) Uani 1 1 d . . . H34 H 0.7232 0.5349 1.5159 0.054 Uiso 1 1 calc R . . C35 C 0.59259(16) 0.49414(7) 1.32172(14) 0.0367(3) Uani 1 1 d . . . H35 H 0.5505 0.4614 1.3656 0.044 Uiso 1 1 calc R . . C36 C 0.54939(14) 0.49709(6) 1.16792(13) 0.0309(3) Uani 1 1 d . . . C41 C 0.2357(2) 0.66830(9) 0.4397(2) 0.0602(5) Uani 1 1 d . . . H41 H 0.2508 0.6730 0.5418 0.072 Uiso 1 1 calc R . . C42 C 0.0982(2) 0.68685(9) 0.3355(2) 0.0569(4) Uani 1 1 d . . . H42 H 0.0196 0.7050 0.3662 0.068 Uiso 1 1 calc R . . C43 C 0.07544(19) 0.67904(8) 0.18767(19) 0.0534(4) Uani 1 1 d . . . H43 H -0.0191 0.6916 0.1163 0.064 Uiso 1 1 calc R . . C44 C 0.1898(2) 0.65299(8) 0.1429(2) 0.0558(4) Uani 1 1 d . . . H44 H 0.1737 0.6471 0.0408 0.067 Uiso 1 1 calc R . . C45 C 0.3279(2) 0.63555(8) 0.2469(2) 0.0568(4) Uani 1 1 d . . . H45 H 0.4073 0.6184 0.2161 0.068 Uiso 1 1 calc R . . C46 C 0.3507(2) 0.64297(8) 0.3952(2) 0.0571(4) Uani 1 1 d . . . H46 H 0.4455 0.6307 0.4665 0.068 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 B1 0.0310(7) 0.0315(7) 0.0312(7) 0.0001(6) 0.0114(6) 0.0040(6) C1 0.0340(7) 0.0353(7) 0.0248(6) -0.0007(5) 0.0076(5) -0.0024(5) C2 0.0390(7) 0.0331(7) 0.0356(7) 0.0006(5) 0.0107(6) -0.0016(6) C3 0.0511(8) 0.0337(8) 0.0500(9) 0.0059(6) 0.0162(7) -0.0007(6) C4 0.0483(8) 0.0417(8) 0.0477(8) 0.0059(7) 0.0177(7) -0.0105(7) C5 0.0366(7) 0.0456(8) 0.0286(6) -0.0010(6) 0.0076(5) -0.0084(6) C6 0.0324(7) 0.0399(7) 0.0242(6) -0.0006(5) 0.0064(5) -0.0025(5) C7 0.0470(8) 0.0414(8) 0.0516(9) 0.0004(7) 0.0203(7) 0.0050(7) C21 0.0381(8) 0.0621(10) 0.0362(8) -0.0036(7) 0.0124(6) -0.0131(7) C22 0.0322(7) 0.0770(12) 0.0389(8) -0.0062(7) 0.0121(6) -0.0011(7) C23 0.0391(8) 0.0609(10) 0.0387(8) -0.0001(7) 0.0097(6) 0.0108(7) C24 0.0386(7) 0.0461(8) 0.0290(6) 0.0022(6) 0.0093(6) 0.0037(6) C31 0.0305(6) 0.0336(7) 0.0288(6) -0.0002(5) 0.0094(5) -0.0004(5) C32 0.0437(8) 0.0443(8) 0.0325(7) -0.0026(6) 0.0104(6) -0.0119(6) C33 0.0528(9) 0.0569(9) 0.0320(7) -0.0075(7) 0.0063(7) -0.0193(7) C34 0.0487(8) 0.0580(9) 0.0245(6) -0.0019(6) 0.0058(6) -0.0072(7) C35 0.0397(7) 0.0407(8) 0.0286(7) 0.0028(5) 0.0101(6) -0.0022(6) C36 0.0310(6) 0.0341(7) 0.0268(6) 0.0009(5) 0.0087(5) 0.0024(5) C41 0.0661(11) 0.0694(12) 0.0494(9) 0.0100(8) 0.0251(8) -0.0034(9) C42 0.0502(9) 0.0674(11) 0.0604(10) 0.0017(8) 0.0282(8) 0.0015(8) C43 0.0444(8) 0.0599(10) 0.0551(10) -0.0010(8) 0.0158(7) -0.0011(7) C44 0.0619(10) 0.0555(10) 0.0524(10) -0.0112(8) 0.0225(8) -0.0021(8) C45 0.0582(10) 0.0449(9) 0.0735(12) -0.0013(8) 0.0303(9) 0.0081(7) C46 0.0537(9) 0.0497(9) 0.0656(11) 0.0183(8) 0.0171(8) 0.0064(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag B1 C36 1.5589(19) 3_667 ? B1 C31 1.5629(18) . ? B1 C1 1.5812(19) . ? C1 C2 1.3810(19) . ? C1 C6 1.4329(18) . ? C2 C3 1.4199(19) . ? C2 C7 1.5089(19) . ? C3 C4 1.365(2) . ? C3 H3 0.9500 . ? C4 C5 1.411(2) . ? C4 H4 0.9500 . ? C5 C21 1.416(2) . ? C5 C6 1.4265(19) . ? C6 C24 1.4149(19) . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C21 C22 1.359(2) . ? C21 H21 0.9500 . ? C22 C23 1.411(2) . ? C22 H22 0.9500 . ? C23 C24 1.3690(19) . ? C23 H23 0.9500 . ? C24 H24 0.9500 . ? C31 C32 1.3951(19) . ? C31 C36 1.4222(17) . ? C32 C33 1.388(2) . ? C32 H32 0.9500 . ? C33 C34 1.382(2) . ? C33 H33 0.9500 . ? C34 C35 1.387(2) . ? C34 H34 0.9500 . ? C35 C36 1.3988(18) . ? C35 H35 0.9500 . ? C36 B1 1.5589(19) 3_667 ? C41 C46 1.378(3) . ? C41 C42 1.385(3) . ? C41 H41 0.9500 . ? C42 C43 1.376(2) . ? C42 H42 0.9500 . ? C43 C44 1.381(2) . ? C43 H43 0.9500 . ? C44 C45 1.382(3) . ? C44 H44 0.9500 . ? C45 C46 1.380(3) . ? C45 H45 0.9500 . ? C46 H46 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 C36 B1 C31 119.35(11) 3_667 . ? C36 B1 C1 120.40(11) 3_667 . ? C31 B1 C1 120.24(11) . . ? C2 C1 C6 119.53(12) . . ? C2 C1 B1 120.14(11) . . ? C6 C1 B1 120.33(11) . . ? C1 C2 C3 119.65(13) . . ? C1 C2 C7 121.24(12) . . ? C3 C2 C7 119.11(13) . . ? C4 C3 C2 121.23(14) . . ? C4 C3 H3 119.4 . . ? C2 C3 H3 119.4 . . ? C3 C4 C5 121.31(13) . . ? C3 C4 H4 119.3 . . ? C5 C4 H4 119.3 . . ? C4 C5 C21 123.19(13) . . ? C4 C5 C6 117.89(13) . . ? C21 C5 C6 118.92(13) . . ? C24 C6 C5 118.04(12) . . ? C24 C6 C1 121.60(12) . . ? C5 C6 C1 120.37(12) . . ? C2 C7 H7A 109.5 . . ? C2 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C2 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C22 C21 C5 121.23(14) . . ? C22 C21 H21 119.4 . . ? C5 C21 H21 119.4 . . ? C21 C22 C23 120.38(13) . . ? C21 C22 H22 119.8 . . ? C23 C22 H22 119.8 . . ? C24 C23 C22 119.70(15) . . ? C24 C23 H23 120.1 . . ? C22 C23 H23 120.1 . . ? C23 C24 C6 121.72(14) . . ? C23 C24 H24 119.1 . . ? C6 C24 H24 119.1 . . ? C32 C31 C36 118.55(11) . . ? C32 C31 B1 120.96(12) . . ? C36 C31 B1 120.49(11) . . ? C33 C32 C31 121.62(13) . . ? C33 C32 H32 119.2 . . ? C31 C32 H32 119.2 . . ? C34 C33 C32 119.95(13) . . ? C34 C33 H33 120.0 . . ? C32 C33 H33 120.0 . . ? C33 C34 C35 119.58(13) . . ? C33 C34 H34 120.2 . . ? C35 C34 H34 120.2 . . ? C34 C35 C36 121.65(13) . . ? C34 C35 H35 119.2 . . ? C36 C35 H35 119.2 . . ? C35 C36 C31 118.64(12) . . ? C35 C36 B1 121.19(12) . 3_667 ? C31 C36 B1 120.16(11) . 3_667 ? C46 C41 C42 119.99(17) . . ? C46 C41 H41 120.0 . . ? C42 C41 H41 120.0 . . ? C43 C42 C41 120.04(16) . . ? C43 C42 H42 120.0 . . ? C41 C42 H42 120.0 . . ? C42 C43 C44 120.07(16) . . ? C42 C43 H43 120.0 . . ? C44 C43 H43 120.0 . . ? C43 C44 C45 119.79(16) . . ? C43 C44 H44 120.1 . . ? C45 C44 H44 120.1 . . ? C46 C45 C44 120.26(16) . . ? C46 C45 H45 119.9 . . ? C44 C45 H45 119.9 . . ? C41 C46 C45 119.82(17) . . ? C41 C46 H46 120.1 . . ? C45 C46 H46 120.1 . . ? 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 C36 B1 C1 C2 93.97(15) 3_667 . . . ? C31 B1 C1 C2 -85.13(15) . . . . ? C36 B1 C1 C6 -85.55(15) 3_667 . . . ? C31 B1 C1 C6 95.35(14) . . . . ? C6 C1 C2 C3 0.44(19) . . . . ? B1 C1 C2 C3 -179.08(12) . . . . ? C6 C1 C2 C7 -179.63(12) . . . . ? B1 C1 C2 C7 0.85(19) . . . . ? C1 C2 C3 C4 0.0(2) . . . . ? C7 C2 C3 C4 -179.95(14) . . . . ? C2 C3 C4 C5 -1.0(2) . . . . ? C3 C4 C5 C21 -179.07(14) . . . . ? C3 C4 C5 C6 1.6(2) . . . . ? C4 C5 C6 C24 178.53(12) . . . . ? C21 C5 C6 C24 -0.83(18) . . . . ? C4 C5 C6 C1 -1.16(19) . . . . ? C21 C5 C6 C1 179.47(12) . . . . ? C2 C1 C6 C24 -179.52(12) . . . . ? B1 C1 C6 C24 0.00(18) . . . . ? C2 C1 C6 C5 0.16(18) . . . . ? B1 C1 C6 C5 179.68(12) . . . . ? C4 C5 C21 C22 -178.55(14) . . . . ? C6 C5 C21 C22 0.8(2) . . . . ? C5 C21 C22 C23 0.0(2) . . . . ? C21 C22 C23 C24 -0.7(2) . . . . ? C22 C23 C24 C6 0.6(2) . . . . ? C5 C6 C24 C23 0.17(19) . . . . ? C1 C6 C24 C23 179.86(12) . . . . ? C36 B1 C31 C32 179.91(12) 3_667 . . . ? C1 B1 C31 C32 -0.98(18) . . . . ? C36 B1 C31 C36 -0.85(19) 3_667 . . . ? C1 B1 C31 C36 178.26(11) . . . . ? C36 C31 C32 C33 -0.1(2) . . . . ? B1 C31 C32 C33 179.20(14) . . . . ? C31 C32 C33 C34 -0.1(2) . . . . ? C32 C33 C34 C35 0.1(2) . . . . ? C33 C34 C35 C36 0.1(2) . . . . ? C34 C35 C36 C31 -0.2(2) . . . . ? C34 C35 C36 B1 179.88(13) . . . 3_667 ? C32 C31 C36 C35 0.22(18) . . . . ? B1 C31 C36 C35 -179.04(11) . . . . ? C32 C31 C36 B1 -179.88(12) . . . 3_667 ? B1 C31 C36 B1 0.86(19) . . . 3_667 ? C46 C41 C42 C43 1.0(3) . . . . ? C41 C42 C43 C44 -0.3(3) . . . . ? C42 C43 C44 C45 -0.8(3) . . . . ? C43 C44 C45 C46 1.2(3) . . . . ? C42 C41 C46 C45 -0.7(3) . . . . ? C44 C45 C46 C41 -0.4(3) . . . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.161 _refine_diff_density_min -0.153 _refine_diff_density_rms 0.037 _database_code_depnum_ccdc_archive 'CCDC 922262' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_global data_wa1500 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C32 H30' _chemical_formula_sum 'C32 H30' _chemical_formula_weight 414.56 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 P21/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 7.2622(4) _cell_length_b 19.4203(12) _cell_length_c 8.8976(5) _cell_angle_alpha 90.00 _cell_angle_beta 100.495(5) _cell_angle_gamma 90.00 _cell_volume 1233.87(12) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 28023 _cell_measurement_theta_min 3.34 _cell_measurement_theta_max 29.04 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.55 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.116 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 444 _exptl_absorpt_coefficient_mu 0.063 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9663 _exptl_absorpt_correction_T_max 0.9876 _exptl_absorpt_process_details 'X-Area (Stoe & Cie, 2001)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Genix 3D I\mS microfocus X-ray source' _diffrn_radiation_monochromator 'Genix 3D multilayer optics' _diffrn_measurement_device_type 'STOE IPDS II two-circle-diffractometer' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 26584 _diffrn_reflns_av_R_equivalents 0.0692 _diffrn_reflns_av_sigmaI/netI 0.0329 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.50 _diffrn_reflns_theta_max 28.67 _reflns_number_total 3144 _reflns_number_gt 2787 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'X-Area (Stoe & Cie, 2001)' _computing_cell_refinement 'X-Area (Stoe & Cie, 2001)' _computing_data_reduction 'X-Area (Stoe & Cie, 2001)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008) ' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008) ' _computing_molecular_graphics 'XP in SHELXTL-Plus (Sheldrick, 2008)' _computing_publication_material SHELXL97 _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^)+(0.0613P)^2^+0.4867P] 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 3144 _refine_ls_number_parameters 148 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0619 _refine_ls_R_factor_gt 0.0541 _refine_ls_wR_factor_ref 0.1442 _refine_ls_wR_factor_gt 0.1392 _refine_ls_goodness_of_fit_ref 1.115 _refine_ls_restrained_S_all 1.115 _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 0.73181(17) 0.41202(6) 0.72500(13) 0.0213(3) Uani 1 1 d . . . C2 C 0.65540(18) 0.35157(6) 0.77344(14) 0.0242(3) Uani 1 1 d . . . C3 C 0.7656(2) 0.31054(7) 0.88337(16) 0.0307(3) Uani 1 1 d . . . H3 H 0.7135 0.2696 0.9166 0.037 Uiso 1 1 calc R . . C4 C 0.9483(2) 0.32771(8) 0.94525(17) 0.0357(3) Uani 1 1 d . . . C5 C 1.0214(2) 0.38761(9) 0.89538(17) 0.0356(3) Uani 1 1 d . . . H5 H 1.1470 0.3999 0.9369 0.043 Uiso 1 1 calc R . . C6 C 0.91678(18) 0.43039(7) 0.78635(15) 0.0280(3) Uani 1 1 d . . . C7 C 0.4572(2) 0.33039(8) 0.71016(19) 0.0366(3) Uani 1 1 d . . . H7A H 0.4232 0.2909 0.7679 0.055 Uiso 1 1 calc R . . H7B H 0.4469 0.3176 0.6024 0.055 Uiso 1 1 calc R . . H7C H 0.3725 0.3689 0.7189 0.055 Uiso 1 1 calc R . . C8 C 1.0659(3) 0.28235(12) 1.0638(3) 0.0616(6) Uani 1 1 d . . . H8A H 0.9837 0.2529 1.1120 0.092 Uiso 1 1 calc R . . H8B H 1.1418 0.3112 1.1417 0.092 Uiso 1 1 calc R . . H8C H 1.1484 0.2535 1.0144 0.092 Uiso 1 1 calc R . . C9 C 1.0031(2) 0.49526(9) 0.7376(2) 0.0430(4) Uani 1 1 d . . . H9A H 0.9580 0.5350 0.7884 0.064 Uiso 1 1 calc R . . H9B H 0.9677 0.5006 0.6265 0.064 Uiso 1 1 calc R . . H9C H 1.1397 0.4924 0.7660 0.064 Uiso 1 1 calc R . . C10 C 0.61428(16) 0.45735(6) 0.60963(13) 0.0209(3) Uani 1 1 d . . . C31 C 0.59039(17) 0.44163(6) 0.45299(13) 0.0215(3) Uani 1 1 d . . . C32 C 0.67997(19) 0.38333(7) 0.39970(15) 0.0264(3) Uani 1 1 d . . . H32 H 0.7588 0.3550 0.4712 0.032 Uiso 1 1 calc R . . C33 C 0.6543(2) 0.36768(7) 0.24820(16) 0.0297(3) Uani 1 1 d . . . H33 H 0.7140 0.3284 0.2152 0.036 Uiso 1 1 calc R . . C34 C 0.5392(2) 0.40965(7) 0.13946(15) 0.0289(3) Uani 1 1 d . . . H34 H 0.5218 0.3982 0.0340 0.035 Uiso 1 1 calc R . . C35 C 0.45324(19) 0.46620(7) 0.18492(14) 0.0254(3) Uani 1 1 d . . . H35 H 0.3775 0.4941 0.1104 0.030 Uiso 1 1 calc R . . C36 C 0.47487(17) 0.48446(6) 0.34278(13) 0.0209(2) 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 0.0221(6) 0.0220(6) 0.0186(5) 0.0000(4) 0.0001(4) 0.0018(4) C2 0.0275(6) 0.0220(6) 0.0221(6) -0.0007(4) 0.0014(5) 0.0009(5) C3 0.0413(8) 0.0221(6) 0.0280(6) 0.0033(5) 0.0044(6) 0.0057(5) C4 0.0376(8) 0.0382(8) 0.0287(7) 0.0041(6) -0.0011(6) 0.0156(6) C5 0.0235(6) 0.0478(9) 0.0318(7) 0.0010(6) -0.0049(5) 0.0056(6) C6 0.0223(6) 0.0333(7) 0.0267(6) 0.0004(5) -0.0005(5) -0.0006(5) C7 0.0346(8) 0.0332(7) 0.0390(8) 0.0039(6) -0.0016(6) -0.0121(6) C8 0.0554(12) 0.0686(13) 0.0545(11) 0.0240(10) -0.0063(9) 0.0281(10) C9 0.0303(7) 0.0488(9) 0.0468(9) 0.0074(7) -0.0009(6) -0.0143(7) C10 0.0206(5) 0.0206(5) 0.0198(5) 0.0011(4) -0.0004(4) -0.0015(4) C31 0.0225(6) 0.0203(5) 0.0207(6) 0.0000(4) 0.0012(4) -0.0010(4) C32 0.0312(7) 0.0225(6) 0.0244(6) 0.0010(5) 0.0021(5) 0.0041(5) C33 0.0380(7) 0.0249(6) 0.0267(6) -0.0027(5) 0.0071(5) 0.0046(5) C34 0.0365(7) 0.0298(7) 0.0198(6) -0.0036(5) 0.0038(5) 0.0007(5) C35 0.0288(6) 0.0264(6) 0.0194(6) 0.0004(4) -0.0003(5) -0.0002(5) C36 0.0209(5) 0.0214(6) 0.0191(5) 0.0006(4) 0.0004(4) -0.0020(4) _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 1.3997(17) . ? C1 C6 1.4009(17) . ? C1 C10 1.4960(16) . ? C2 C3 1.3952(18) . ? C2 C7 1.5040(19) . ? C3 C4 1.381(2) . ? C3 H3 0.9500 . ? C4 C5 1.385(2) . ? C4 C8 1.513(2) . ? C5 C6 1.3929(19) . ? C5 H5 0.9500 . ? C6 C9 1.506(2) . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 C36 1.4056(17) 3_666 ? C10 C31 1.4062(16) . ? C31 C32 1.4292(17) . ? C31 C36 1.4344(16) . ? C32 C33 1.3611(18) . ? C32 H32 0.9500 . ? C33 C34 1.4160(19) . ? C33 H33 0.9500 . ? C34 C35 1.3607(19) . ? C34 H34 0.9500 . ? C35 C36 1.4293(17) . ? C35 H35 0.9500 . ? C36 C10 1.4055(17) 3_666 ? 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 119.96(11) . . ? C2 C1 C10 119.75(11) . . ? C6 C1 C10 120.28(11) . . ? C3 C2 C1 119.07(12) . . ? C3 C2 C7 119.59(12) . . ? C1 C2 C7 121.34(11) . . ? C4 C3 C2 121.88(13) . . ? C4 C3 H3 119.1 . . ? C2 C3 H3 119.1 . . ? C3 C4 C5 118.14(13) . . ? C3 C4 C8 121.11(16) . . ? C5 C4 C8 120.76(16) . . ? C4 C5 C6 122.11(13) . . ? C4 C5 H5 118.9 . . ? C6 C5 H5 118.9 . . ? C5 C6 C1 118.84(13) . . ? C5 C6 C9 119.78(13) . . ? C1 C6 C9 121.38(12) . . ? C2 C7 H7A 109.5 . . ? C2 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C2 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C4 C8 H8A 109.5 . . ? C4 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C4 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C6 C9 H9A 109.5 . . ? C6 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C6 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C36 C10 C31 119.51(10) 3_666 . ? C36 C10 C1 120.19(10) 3_666 . ? C31 C10 C1 120.29(11) . . ? C10 C31 C32 121.28(11) . . ? C10 C31 C36 120.19(11) . . ? C32 C31 C36 118.52(11) . . ? C33 C32 C31 121.13(12) . . ? C33 C32 H32 119.4 . . ? C31 C32 H32 119.4 . . ? C32 C33 C34 120.36(12) . . ? C32 C33 H33 119.8 . . ? C34 C33 H33 119.8 . . ? C35 C34 C33 120.48(12) . . ? C35 C34 H34 119.8 . . ? C33 C34 H34 119.8 . . ? C34 C35 C36 121.21(12) . . ? C34 C35 H35 119.4 . . ? C36 C35 H35 119.4 . . ? C10 C36 C35 121.42(11) 3_666 . ? C10 C36 C31 120.29(10) 3_666 . ? C35 C36 C31 118.28(11) . . ? 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 0.28(19) . . . . ? C10 C1 C2 C3 -178.73(12) . . . . ? C6 C1 C2 C7 179.88(13) . . . . ? C10 C1 C2 C7 0.88(19) . . . . ? C1 C2 C3 C4 -0.3(2) . . . . ? C7 C2 C3 C4 -179.92(14) . . . . ? C2 C3 C4 C5 0.1(2) . . . . ? C2 C3 C4 C8 -179.68(16) . . . . ? C3 C4 C5 C6 0.2(2) . . . . ? C8 C4 C5 C6 179.94(16) . . . . ? C4 C5 C6 C1 -0.2(2) . . . . ? C4 C5 C6 C9 179.40(15) . . . . ? C2 C1 C6 C5 0.0(2) . . . . ? C10 C1 C6 C5 178.97(12) . . . . ? C2 C1 C6 C9 -179.63(14) . . . . ? C10 C1 C6 C9 -0.6(2) . . . . ? C2 C1 C10 C36 97.80(14) . . . 3_666 ? C6 C1 C10 C36 -81.21(16) . . . 3_666 ? C2 C1 C10 C31 -81.46(15) . . . . ? C6 C1 C10 C31 99.54(15) . . . . ? C36 C10 C31 C32 179.41(11) 3_666 . . . ? C1 C10 C31 C32 -1.33(18) . . . . ? C36 C10 C31 C36 -0.40(19) 3_666 . . . ? C1 C10 C31 C36 178.86(11) . . . . ? C10 C31 C32 C33 179.01(13) . . . . ? C36 C31 C32 C33 -1.17(19) . . . . ? C31 C32 C33 C34 0.7(2) . . . . ? C32 C33 C34 C35 0.2(2) . . . . ? C33 C34 C35 C36 -0.6(2) . . . . ? C34 C35 C36 C10 -179.71(12) . . . 3_666 ? C34 C35 C36 C31 0.15(19) . . . . ? C10 C31 C36 C10 0.41(19) . . . 3_666 ? C32 C31 C36 C10 -179.41(11) . . . 3_666 ? C10 C31 C36 C35 -179.46(11) . . . . ? C32 C31 C36 C35 0.73(17) . . . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.284 _refine_diff_density_min -0.228 _refine_diff_density_rms 0.044 _database_code_depnum_ccdc_archive 'CCDC 922263' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_global data_wa1443 #TrackingRef 'deposit.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C36 H26, 2(C6 H6)' _chemical_formula_sum 'C48 H38' _chemical_formula_weight 614.78 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 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.1166(17) _cell_length_b 9.4240(18) _cell_length_c 10.5376(18) _cell_angle_alpha 87.558(15) _cell_angle_beta 81.861(14) _cell_angle_gamma 71.156(15) _cell_volume 848.2(3) _cell_formula_units_Z 1 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 9987 _cell_measurement_theta_min 3.3 _cell_measurement_theta_max 26.1 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.204 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 326 _exptl_absorpt_coefficient_mu 0.068 _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 'Genix 3D I\mS microfocus X-ray source' _diffrn_radiation_monochromator 'Genix 3D multilayer optics' _diffrn_measurement_device_type 'STOE IPDS II two-circle-diffractometer' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 7523 _diffrn_reflns_av_R_equivalents 0.1172 _diffrn_reflns_av_sigmaI/netI 0.0950 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.28 _diffrn_reflns_theta_max 25.03 _reflns_number_total 2969 _reflns_number_gt 2106 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'X-Area (Stoe & Cie, 2001)' _computing_cell_refinement 'X-Area (Stoe & Cie, 2001)' _computing_data_reduction 'X-Area (Stoe & Cie, 2001)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008) ' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008) ' _computing_molecular_graphics 'XP in SHELXTL-Plus (Sheldrick, 2008)' _computing_publication_material SHELXL97 _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^)+(0.0369P)^2^+1.5086P] 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 2969 _refine_ls_number_parameters 218 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1325 _refine_ls_R_factor_gt 0.0988 _refine_ls_wR_factor_ref 0.2104 _refine_ls_wR_factor_gt 0.1984 _refine_ls_goodness_of_fit_ref 1.134 _refine_ls_restrained_S_all 1.134 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.0980(5) 0.6393(4) 0.2013(3) 0.0278(8) Uani 1 1 d . . . C2 C 0.0132(5) 0.6640(4) 0.3218(4) 0.0335(9) Uani 1 1 d . . . C3 C 0.0628(6) 0.7323(5) 0.4173(4) 0.0420(11) Uani 1 1 d . . . H3 H 0.0023 0.7510 0.4996 0.050 Uiso 1 1 calc R . . C4 C 0.1947(5) 0.7716(5) 0.3939(4) 0.0400(10) Uani 1 1 d . . . H4 H 0.2257 0.8162 0.4603 0.048 Uiso 1 1 calc R . . C5 C 0.2863(5) 0.7473(4) 0.2725(4) 0.0347(9) Uani 1 1 d . . . C6 C 0.2367(4) 0.6805(4) 0.1741(3) 0.0288(8) Uani 1 1 d . . . C7 C -0.1348(5) 0.6207(5) 0.3546(4) 0.0437(11) Uani 1 1 d . . . H7A H -0.1939 0.6425 0.2814 0.066 Uiso 1 1 calc R . . H7B H -0.1991 0.6785 0.4294 0.066 Uiso 1 1 calc R . . H7C H -0.1065 0.5134 0.3741 0.066 Uiso 1 1 calc R . . C10 C 0.0475(4) 0.5679(4) 0.0989(3) 0.0271(8) Uani 1 1 d . . . C21 C 0.4232(5) 0.7884(5) 0.2442(4) 0.0420(11) Uani 1 1 d . . . H21 H 0.4585 0.8299 0.3099 0.050 Uiso 1 1 calc R . . C22 C 0.5053(5) 0.7697(5) 0.1248(5) 0.0461(11) Uani 1 1 d . . . H22 H 0.5953 0.8009 0.1070 0.055 Uiso 1 1 calc R . . C23 C 0.4578(5) 0.7046(5) 0.0277(5) 0.0429(10) Uani 1 1 d . . . H23 H 0.5167 0.6906 -0.0554 0.052 Uiso 1 1 calc R . . C24 C 0.3266(5) 0.6609(4) 0.0519(4) 0.0330(9) Uani 1 1 d . . . H24 H 0.2960 0.6167 -0.0149 0.040 Uiso 1 1 calc R . . C31 C 0.0860(4) 0.4112(4) 0.0925(3) 0.0268(8) Uani 1 1 d . . . C32 C 0.1723(5) 0.3138(5) 0.1825(4) 0.0332(9) Uani 1 1 d . . . H32 H 0.2044 0.3565 0.2493 0.040 Uiso 1 1 calc R . . C33 C 0.2095(5) 0.1661(5) 0.1768(4) 0.0376(10) Uani 1 1 d . . . H33 H 0.2682 0.1058 0.2385 0.045 Uiso 1 1 calc R . . C34 C 0.1620(5) 0.0957(5) 0.0784(4) 0.0359(9) Uani 1 1 d . . . H34 H 0.1883 -0.0103 0.0753 0.043 Uiso 1 1 calc R . . C35 C 0.0800(4) 0.1821(4) -0.0094(4) 0.0297(8) Uani 1 1 d . . . H35 H 0.0490 0.1356 -0.0745 0.036 Uiso 1 1 calc R . . C36 C 0.0382(4) 0.3421(4) -0.0069(3) 0.0255(8) Uani 1 1 d . . . C41 C 0.3844(6) 0.6273(6) 0.6814(4) 0.0472(11) Uani 1 1 d . . . H41 H 0.3963 0.5235 0.6877 0.057 Uiso 1 1 calc R . . C42 C 0.2445(6) 0.7321(6) 0.7269(4) 0.0488(12) Uani 1 1 d . . . H42 H 0.1595 0.7000 0.7644 0.059 Uiso 1 1 calc R . . C43 C 0.2260(6) 0.8809(6) 0.7191(4) 0.0539(13) Uani 1 1 d . . . H43 H 0.1288 0.9524 0.7510 0.065 Uiso 1 1 calc R . . C44 C 0.3499(7) 0.9279(6) 0.6643(5) 0.0578(14) Uani 1 1 d . . . H44 H 0.3378 1.0319 0.6586 0.069 Uiso 1 1 calc R . . C45 C 0.4906(6) 0.8234(6) 0.6183(5) 0.0526(13) Uani 1 1 d . . . H45 H 0.5760 0.8550 0.5809 0.063 Uiso 1 1 calc R . . C46 C 0.5068(6) 0.6734(6) 0.6268(4) 0.0474(11) Uani 1 1 d . . . H46 H 0.6035 0.6013 0.5946 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 C1 0.034(2) 0.0219(19) 0.0313(18) 0.0015(14) -0.0096(15) -0.0122(16) C2 0.039(2) 0.028(2) 0.035(2) 0.0006(16) -0.0053(16) -0.0126(18) C3 0.055(3) 0.048(3) 0.0262(19) -0.0020(17) -0.0071(18) -0.019(2) C4 0.057(3) 0.036(2) 0.034(2) -0.0020(17) -0.0164(19) -0.020(2) C5 0.041(2) 0.025(2) 0.043(2) 0.0039(16) -0.0172(18) -0.0137(18) C6 0.032(2) 0.0216(19) 0.0338(19) 0.0028(14) -0.0104(15) -0.0074(16) C7 0.043(3) 0.047(3) 0.042(2) -0.0035(19) 0.0061(18) -0.020(2) C10 0.0265(19) 0.028(2) 0.0292(18) -0.0010(14) -0.0029(14) -0.0113(16) C21 0.043(3) 0.033(2) 0.059(3) 0.0025(19) -0.026(2) -0.015(2) C22 0.032(2) 0.040(3) 0.071(3) 0.002(2) -0.009(2) -0.017(2) C23 0.035(2) 0.040(3) 0.055(3) -0.0003(19) 0.0000(19) -0.017(2) C24 0.032(2) 0.030(2) 0.038(2) -0.0041(16) -0.0049(16) -0.0105(17) C31 0.0241(19) 0.027(2) 0.0313(18) -0.0012(14) -0.0031(14) -0.0108(16) C32 0.036(2) 0.033(2) 0.035(2) 0.0037(16) -0.0122(16) -0.0144(18) C33 0.043(2) 0.031(2) 0.040(2) 0.0050(17) -0.0171(18) -0.0087(19) C34 0.039(2) 0.025(2) 0.046(2) 0.0011(16) -0.0114(18) -0.0115(18) C35 0.029(2) 0.027(2) 0.0362(19) -0.0019(15) -0.0060(15) -0.0114(17) C36 0.0266(19) 0.0253(19) 0.0270(17) -0.0006(14) -0.0013(14) -0.0124(16) C41 0.052(3) 0.050(3) 0.046(2) 0.011(2) -0.015(2) -0.023(2) C42 0.056(3) 0.064(3) 0.037(2) 0.003(2) -0.003(2) -0.036(3) C43 0.059(3) 0.063(3) 0.041(2) -0.020(2) 0.002(2) -0.021(3) C44 0.085(4) 0.046(3) 0.058(3) -0.003(2) -0.016(3) -0.039(3) C45 0.054(3) 0.072(4) 0.048(3) 0.006(2) -0.010(2) -0.041(3) C46 0.040(3) 0.056(3) 0.050(3) 0.003(2) -0.012(2) -0.017(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 C1 C2 1.377(5) . ? C1 C6 1.427(5) . ? C1 C10 1.494(5) . ? C2 C3 1.415(6) . ? C2 C7 1.522(6) . ? C3 C4 1.356(6) . ? C3 H3 0.9500 . ? C4 C5 1.410(6) . ? C4 H4 0.9500 . ? C5 C21 1.412(6) . ? C5 C6 1.431(5) . ? C6 C24 1.410(5) . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C10 C31 1.406(5) . ? C10 C36 1.409(5) 2_565 ? C21 C22 1.357(7) . ? C21 H21 0.9500 . ? C22 C23 1.400(7) . ? C22 H22 0.9500 . ? C23 C24 1.374(6) . ? C23 H23 0.9500 . ? C24 H24 0.9500 . ? C31 C32 1.425(5) . ? C31 C36 1.444(5) . ? C32 C33 1.324(6) . ? C32 H32 0.9500 . ? C33 C34 1.440(6) . ? C33 H33 0.9500 . ? C34 C35 1.347(5) . ? C34 H34 0.9500 . ? C35 C36 1.431(5) . ? C35 H35 0.9500 . ? C36 C10 1.409(5) 2_565 ? C41 C46 1.369(7) . ? C41 C42 1.373(7) . ? C41 H41 0.9500 . ? C42 C43 1.358(7) . ? C42 H42 0.9500 . ? C43 C44 1.386(8) . ? C43 H43 0.9500 . ? C44 C45 1.378(8) . ? C44 H44 0.9500 . ? C45 C46 1.373(7) . ? C45 H45 0.9500 . ? C46 H46 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C6 119.8(3) . . ? C2 C1 C10 120.7(3) . . ? C6 C1 C10 119.5(3) . . ? C1 C2 C3 119.8(4) . . ? C1 C2 C7 121.3(3) . . ? C3 C2 C7 118.9(4) . . ? C4 C3 C2 121.5(4) . . ? C4 C3 H3 119.2 . . ? C2 C3 H3 119.2 . . ? C3 C4 C5 120.8(4) . . ? C3 C4 H4 119.6 . . ? C5 C4 H4 119.6 . . ? C4 C5 C21 122.4(4) . . ? C4 C5 C6 118.4(4) . . ? C21 C5 C6 119.1(4) . . ? C24 C6 C1 122.4(3) . . ? C24 C6 C5 117.9(4) . . ? C1 C6 C5 119.7(3) . . ? C2 C7 H7A 109.5 . . ? C2 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C2 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C31 C10 C36 119.5(3) . 2_565 ? C31 C10 C1 120.6(3) . . ? C36 C10 C1 119.9(3) 2_565 . ? C22 C21 C5 121.1(4) . . ? C22 C21 H21 119.4 . . ? C5 C21 H21 119.4 . . ? C21 C22 C23 120.3(4) . . ? C21 C22 H22 119.9 . . ? C23 C22 H22 119.9 . . ? C24 C23 C22 120.3(4) . . ? C24 C23 H23 119.8 . . ? C22 C23 H23 119.8 . . ? C23 C24 C6 121.2(4) . . ? C23 C24 H24 119.4 . . ? C6 C24 H24 119.4 . . ? C10 C31 C32 122.4(3) . . ? C10 C31 C36 120.6(3) . . ? C32 C31 C36 117.0(3) . . ? C33 C32 C31 122.7(4) . . ? C33 C32 H32 118.7 . . ? C31 C32 H32 118.7 . . ? C32 C33 C34 120.9(4) . . ? C32 C33 H33 119.6 . . ? C34 C33 H33 119.6 . . ? C35 C34 C33 119.2(4) . . ? C35 C34 H34 120.4 . . ? C33 C34 H34 120.4 . . ? C34 C35 C36 121.7(3) . . ? C34 C35 H35 119.2 . . ? C36 C35 H35 119.2 . . ? C10 C36 C35 121.5(3) 2_565 . ? C10 C36 C31 119.9(3) 2_565 . ? C35 C36 C31 118.6(3) . . ? C46 C41 C42 119.6(5) . . ? C46 C41 H41 120.2 . . ? C42 C41 H41 120.2 . . ? C43 C42 C41 120.9(5) . . ? C43 C42 H42 119.6 . . ? C41 C42 H42 119.6 . . ? C42 C43 C44 119.6(5) . . ? C42 C43 H43 120.2 . . ? C44 C43 H43 120.2 . . ? C45 C44 C43 119.8(5) . . ? C45 C44 H44 120.1 . . ? C43 C44 H44 120.1 . . ? C46 C45 C44 119.7(5) . . ? C46 C45 H45 120.2 . . ? C44 C45 H45 120.2 . . ? C41 C46 C45 120.4(5) . . ? C41 C46 H46 119.8 . . ? C45 C46 H46 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 C6 C1 C2 C3 1.1(6) . . . . ? C10 C1 C2 C3 -179.8(4) . . . . ? C6 C1 C2 C7 -179.7(4) . . . . ? C10 C1 C2 C7 -0.5(6) . . . . ? C1 C2 C3 C4 -1.5(7) . . . . ? C7 C2 C3 C4 179.3(4) . . . . ? C2 C3 C4 C5 0.8(7) . . . . ? C3 C4 C5 C21 179.2(4) . . . . ? C3 C4 C5 C6 0.2(6) . . . . ? C2 C1 C6 C24 -178.7(4) . . . . ? C10 C1 C6 C24 2.1(5) . . . . ? C2 C1 C6 C5 -0.1(5) . . . . ? C10 C1 C6 C5 -179.3(3) . . . . ? C4 C5 C6 C24 178.1(4) . . . . ? C21 C5 C6 C24 -1.0(5) . . . . ? C4 C5 C6 C1 -0.6(5) . . . . ? C21 C5 C6 C1 -179.6(4) . . . . ? C2 C1 C10 C31 -82.5(5) . . . . ? C6 C1 C10 C31 96.7(4) . . . . ? C2 C1 C10 C36 98.2(4) . . . 2_565 ? C6 C1 C10 C36 -82.7(5) . . . 2_565 ? C4 C5 C21 C22 -177.0(4) . . . . ? C6 C5 C21 C22 2.0(6) . . . . ? C5 C21 C22 C23 -1.9(7) . . . . ? C21 C22 C23 C24 0.9(7) . . . . ? C22 C23 C24 C6 0.1(6) . . . . ? C1 C6 C24 C23 178.6(4) . . . . ? C5 C6 C24 C23 -0.1(6) . . . . ? C36 C10 C31 C32 -179.9(4) 2_565 . . . ? C1 C10 C31 C32 0.7(5) . . . . ? C36 C10 C31 C36 -0.2(6) 2_565 . . . ? C1 C10 C31 C36 -179.5(3) . . . . ? C10 C31 C32 C33 -179.7(4) . . . . ? C36 C31 C32 C33 0.5(6) . . . . ? C31 C32 C33 C34 -0.7(7) . . . . ? C32 C33 C34 C35 0.6(6) . . . . ? C33 C34 C35 C36 -0.2(6) . . . . ? C34 C35 C36 C10 179.9(4) . . . 2_565 ? C34 C35 C36 C31 0.0(5) . . . . ? C10 C31 C36 C10 0.2(6) . . . 2_565 ? C32 C31 C36 C10 180.0(3) . . . 2_565 ? C10 C31 C36 C35 -179.9(3) . . . . ? C32 C31 C36 C35 -0.1(5) . . . . ? C46 C41 C42 C43 -0.3(7) . . . . ? C41 C42 C43 C44 0.1(7) . . . . ? C42 C43 C44 C45 0.0(7) . . . . ? C43 C44 C45 C46 0.2(7) . . . . ? C42 C41 C46 C45 0.5(7) . . . . ? C44 C45 C46 C41 -0.4(7) . . . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.217 _refine_diff_density_min -0.259 _refine_diff_density_rms 0.053 _database_code_depnum_ccdc_archive 'CCDC 922264' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_global data_wa1532 #TrackingRef 'deposit.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C36 H26, 2(C6 H6)' _chemical_formula_sum 'C48 H38' _chemical_formula_weight 614.78 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 19.6910(15) _cell_length_b 9.7696(5) _cell_length_c 18.3312(14) _cell_angle_alpha 90.00 _cell_angle_beta 101.556(6) _cell_angle_gamma 90.00 _cell_volume 3454.9(4) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 31357 _cell_measurement_theta_min 3.39 _cell_measurement_theta_max 26.13 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.48 _exptl_crystal_size_min 0.38 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.182 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1304 _exptl_absorpt_coefficient_mu 0.067 _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 'Genix 3D I\mS microfocus X-ray source' _diffrn_radiation_monochromator 'Genix 3D multilayer optics' _diffrn_measurement_device_type 'STOE IPDS II two-circle-diffractometer' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 23515 _diffrn_reflns_av_R_equivalents 0.0548 _diffrn_reflns_av_sigmaI/netI 0.0243 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 3.40 _diffrn_reflns_theta_max 25.69 _reflns_number_total 3235 _reflns_number_gt 2939 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'X-Area (Stoe & Cie, 2001)' _computing_cell_refinement 'X-Area (Stoe & Cie, 2001)' _computing_data_reduction 'X-Area (Stoe & Cie, 2001)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008) ' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008) ' _computing_molecular_graphics 'XP in SHELXTL-Plus (Sheldrick, 2008)' _computing_publication_material SHELXL97 _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^)+(0.0559P)^2^+2.5672P] 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 3235 _refine_ls_number_parameters 218 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0543 _refine_ls_R_factor_gt 0.0486 _refine_ls_wR_factor_ref 0.1316 _refine_ls_wR_factor_gt 0.1281 _refine_ls_goodness_of_fit_ref 1.143 _refine_ls_restrained_S_all 1.143 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.62476(7) 0.59085(15) 0.68676(7) 0.0242(3) Uani 1 1 d . . . C2 C 0.66414(8) 0.70586(16) 0.68165(8) 0.0293(3) Uani 1 1 d . . . C3 C 0.72455(8) 0.69308(18) 0.65047(9) 0.0371(4) Uani 1 1 d . . . H3 H 0.7519 0.7720 0.6470 0.045 Uiso 1 1 calc R . . C4 C 0.74397(8) 0.57133(18) 0.62566(9) 0.0363(4) Uani 1 1 d . . . H4 H 0.7842 0.5666 0.6046 0.044 Uiso 1 1 calc R . . C5 C 0.70520(7) 0.45167(16) 0.63072(8) 0.0289(3) Uani 1 1 d . . . C6 C 0.64425(7) 0.46074(15) 0.66161(7) 0.0237(3) Uani 1 1 d . . . C7 C 0.64527(9) 0.84258(17) 0.70852(10) 0.0379(4) Uani 1 1 d . . . H7A H 0.5965 0.8622 0.6874 0.057 Uiso 1 1 calc R . . H7B H 0.6745 0.9134 0.6928 0.057 Uiso 1 1 calc R . . H7C H 0.6524 0.8417 0.7630 0.057 Uiso 1 1 calc R . . C10 C 0.56082(7) 0.59862(14) 0.71909(7) 0.0219(3) Uani 1 1 d . . . C21 C 0.72438(8) 0.32343(18) 0.60578(9) 0.0357(4) Uani 1 1 d . . . H21 H 0.7651 0.3163 0.5857 0.043 Uiso 1 1 calc R . . C22 C 0.68538(9) 0.20952(18) 0.61011(10) 0.0395(4) Uani 1 1 d . . . H22 H 0.6989 0.1241 0.5928 0.047 Uiso 1 1 calc R . . C23 C 0.62519(9) 0.21835(17) 0.64021(9) 0.0360(4) Uani 1 1 d . . . H23 H 0.5981 0.1388 0.6429 0.043 Uiso 1 1 calc R . . C24 C 0.60553(8) 0.34048(16) 0.66552(8) 0.0292(3) Uani 1 1 d . . . H24 H 0.5650 0.3446 0.6862 0.035 Uiso 1 1 calc R . . C31 C 0.56630(7) 0.59746(13) 0.79696(7) 0.0217(3) Uani 1 1 d . . . C32 C 0.63218(7) 0.59084(15) 0.84689(8) 0.0269(3) Uani 1 1 d . . . H32 H 0.6732 0.5865 0.8272 0.032 Uiso 1 1 calc R . . C33 C 0.63709(8) 0.59064(16) 0.92197(8) 0.0308(4) Uani 1 1 d . . . H33 H 0.6814 0.5853 0.9540 0.037 Uiso 1 1 calc R . . C34 C 0.57676(8) 0.59831(16) 0.95272(8) 0.0297(3) Uani 1 1 d . . . H34 H 0.5809 0.6006 1.0052 0.036 Uiso 1 1 calc R . . C35 C 0.51291(8) 0.60250(15) 0.90757(8) 0.0261(3) Uani 1 1 d . . . H35 H 0.4729 0.6068 0.9291 0.031 Uiso 1 1 calc R . . C36 C 0.50499(7) 0.60047(13) 0.82810(7) 0.0215(3) Uani 1 1 d . . . C41 C 0.92748(14) 0.4822(2) 0.55198(13) 0.0643(6) Uani 1 1 d . . . H41 H 0.9326 0.3998 0.5261 0.077 Uiso 1 1 calc R . . C42 C 0.90928(17) 0.6004(2) 0.51318(13) 0.0752(8) Uani 1 1 d . . . H42 H 0.9017 0.5995 0.4603 0.090 Uiso 1 1 calc R . . C43 C 0.90184(13) 0.7194(2) 0.54930(13) 0.0619(6) Uani 1 1 d . . . H43 H 0.8887 0.8009 0.5218 0.074 Uiso 1 1 calc R . . C44 C 0.91342(10) 0.7212(2) 0.62565(12) 0.0520(5) Uani 1 1 d . . . H44 H 0.9092 0.8043 0.6512 0.062 Uiso 1 1 calc R . . C45 C 0.93116(9) 0.6020(2) 0.66510(11) 0.0526(5) Uani 1 1 d . . . H45 H 0.9385 0.6024 0.7179 0.063 Uiso 1 1 calc R . . C46 C 0.93823(10) 0.4824(2) 0.62762(12) 0.0520(5) Uani 1 1 d . . . H46 H 0.9506 0.4000 0.6546 0.062 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 0.0229(7) 0.0297(8) 0.0193(6) 0.0033(5) 0.0030(5) 0.0006(6) C2 0.0291(7) 0.0319(8) 0.0264(7) 0.0038(6) 0.0042(6) -0.0026(6) C3 0.0285(8) 0.0415(9) 0.0429(9) 0.0048(7) 0.0107(7) -0.0075(7) C4 0.0237(7) 0.0481(10) 0.0390(9) 0.0040(7) 0.0107(6) -0.0016(7) C5 0.0226(7) 0.0384(9) 0.0245(7) 0.0031(6) 0.0020(5) 0.0056(6) C6 0.0213(6) 0.0310(8) 0.0177(6) 0.0028(5) 0.0016(5) 0.0029(5) C7 0.0418(9) 0.0303(9) 0.0429(9) 0.0010(7) 0.0118(7) -0.0065(7) C10 0.0244(7) 0.0202(7) 0.0219(7) 0.0008(5) 0.0062(5) -0.0002(5) C21 0.0273(7) 0.0468(10) 0.0330(8) 0.0021(7) 0.0062(6) 0.0145(7) C22 0.0411(9) 0.0351(9) 0.0421(9) -0.0024(7) 0.0076(7) 0.0149(7) C23 0.0420(9) 0.0263(8) 0.0400(9) 0.0014(7) 0.0090(7) 0.0037(7) C24 0.0306(7) 0.0297(8) 0.0281(7) 0.0025(6) 0.0079(6) 0.0038(6) C31 0.0237(7) 0.0194(7) 0.0219(7) 0.0006(5) 0.0040(5) -0.0032(5) C32 0.0228(7) 0.0319(8) 0.0254(7) 0.0021(6) 0.0034(5) -0.0065(6) C33 0.0269(7) 0.0373(9) 0.0250(7) 0.0035(6) -0.0025(6) -0.0098(6) C34 0.0372(8) 0.0338(8) 0.0174(7) 0.0003(6) 0.0035(6) -0.0110(6) C35 0.0299(7) 0.0273(8) 0.0220(7) -0.0014(6) 0.0075(5) -0.0070(6) C36 0.0255(7) 0.0191(7) 0.0204(6) -0.0007(5) 0.0053(5) -0.0034(5) C41 0.0937(17) 0.0399(11) 0.0664(14) -0.0105(10) 0.0325(13) 0.0039(11) C42 0.128(2) 0.0554(14) 0.0485(12) 0.0019(10) 0.0329(14) 0.0043(14) C43 0.0813(15) 0.0377(11) 0.0731(15) 0.0104(10) 0.0306(12) -0.0010(10) C44 0.0439(10) 0.0403(11) 0.0730(14) -0.0183(10) 0.0146(9) -0.0088(8) C45 0.0369(9) 0.0715(14) 0.0463(11) -0.0071(10) 0.0012(8) 0.0017(9) C46 0.0438(10) 0.0454(11) 0.0684(13) 0.0132(10) 0.0154(9) 0.0095(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.379(2) . ? C1 C6 1.431(2) . ? C1 C10 1.4970(18) . ? C2 C3 1.425(2) . ? C2 C7 1.496(2) . ? C3 C4 1.356(2) . ? C3 H3 0.9500 . ? C4 C5 1.409(2) . ? C4 H4 0.9500 . ? C5 C21 1.411(2) . ? C5 C6 1.4287(19) . ? C6 C24 1.410(2) . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C10 C36 1.4067(19) 2_656 ? C10 C31 1.4099(19) . ? C21 C22 1.363(3) . ? C21 H21 0.9500 . ? C22 C23 1.406(2) . ? C22 H22 0.9500 . ? C23 C24 1.364(2) . ? C23 H23 0.9500 . ? C24 H24 0.9500 . ? C31 C32 1.4313(19) . ? C31 C36 1.4354(19) . ? C32 C33 1.360(2) . ? C32 H32 0.9500 . ? C33 C34 1.415(2) . ? C33 H33 0.9500 . ? C34 C35 1.360(2) . ? C34 H34 0.9500 . ? C35 C36 1.4338(19) . ? C35 H35 0.9500 . ? C36 C10 1.4067(19) 2_656 ? C41 C46 1.360(3) . ? C41 C42 1.366(3) . ? C41 H41 0.9500 . ? C42 C43 1.360(3) . ? C42 H42 0.9500 . ? C43 C44 1.372(3) . ? C43 H43 0.9500 . ? C44 C45 1.378(3) . ? C44 H44 0.9500 . ? C45 C46 1.377(3) . ? C45 H45 0.9500 . ? C46 H46 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C6 120.74(13) . . ? C2 C1 C10 120.97(13) . . ? C6 C1 C10 118.29(12) . . ? C1 C2 C3 118.81(14) . . ? C1 C2 C7 121.66(13) . . ? C3 C2 C7 119.52(14) . . ? C4 C3 C2 121.72(15) . . ? C4 C3 H3 119.1 . . ? C2 C3 H3 119.1 . . ? C3 C4 C5 120.86(14) . . ? C3 C4 H4 119.6 . . ? C5 C4 H4 119.6 . . ? C4 C5 C21 122.11(14) . . ? C4 C5 C6 118.92(14) . . ? C21 C5 C6 118.96(14) . . ? C24 C6 C5 118.31(13) . . ? C24 C6 C1 122.76(12) . . ? C5 C6 C1 118.93(13) . . ? C2 C7 H7A 109.5 . . ? C2 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C2 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C36 C10 C31 119.81(12) 2_656 . ? C36 C10 C1 120.09(12) 2_656 . ? C31 C10 C1 120.03(12) . . ? C22 C21 C5 121.02(14) . . ? C22 C21 H21 119.5 . . ? C5 C21 H21 119.5 . . ? C21 C22 C23 120.11(15) . . ? C21 C22 H22 119.9 . . ? C23 C22 H22 119.9 . . ? C24 C23 C22 120.39(15) . . ? C24 C23 H23 119.8 . . ? C22 C23 H23 119.8 . . ? C23 C24 C6 121.21(14) . . ? C23 C24 H24 119.4 . . ? C6 C24 H24 119.4 . . ? C10 C31 C32 121.57(12) . . ? C10 C31 C36 120.17(12) . . ? C32 C31 C36 118.25(12) . . ? C33 C32 C31 121.24(13) . . ? C33 C32 H32 119.4 . . ? C31 C32 H32 119.4 . . ? C32 C33 C34 120.51(13) . . ? C32 C33 H33 119.7 . . ? C34 C33 H33 119.7 . . ? C35 C34 C33 120.44(13) . . ? C35 C34 H34 119.8 . . ? C33 C34 H34 119.8 . . ? C34 C35 C36 121.11(13) . . ? C34 C35 H35 119.4 . . ? C36 C35 H35 119.4 . . ? C10 C36 C35 121.61(12) 2_656 . ? C10 C36 C31 119.98(12) 2_656 . ? C35 C36 C31 118.39(12) . . ? C46 C41 C42 120.0(2) . . ? C46 C41 H41 120.0 . . ? C42 C41 H41 120.0 . . ? C43 C42 C41 120.8(2) . . ? C43 C42 H42 119.6 . . ? C41 C42 H42 119.6 . . ? C42 C43 C44 119.7(2) . . ? C42 C43 H43 120.2 . . ? C44 C43 H43 120.2 . . ? C43 C44 C45 119.81(19) . . ? C43 C44 H44 120.1 . . ? C45 C44 H44 120.1 . . ? C46 C45 C44 119.71(19) . . ? C46 C45 H45 120.1 . . ? C44 C45 H45 120.1 . . ? C41 C46 C45 120.0(2) . . ? C41 C46 H46 120.0 . . ? C45 C46 H46 120.0 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 0.3(2) . . . . ? C10 C1 C2 C3 179.97(13) . . . . ? C6 C1 C2 C7 -179.17(13) . . . . ? C10 C1 C2 C7 0.5(2) . . . . ? C1 C2 C3 C4 0.2(2) . . . . ? C7 C2 C3 C4 179.71(15) . . . . ? C2 C3 C4 C5 -0.8(3) . . . . ? C3 C4 C5 C21 -179.61(15) . . . . ? C3 C4 C5 C6 0.8(2) . . . . ? C4 C5 C6 C24 179.27(13) . . . . ? C21 C5 C6 C24 -0.29(19) . . . . ? C4 C5 C6 C1 -0.33(19) . . . . ? C21 C5 C6 C1 -179.89(13) . . . . ? C2 C1 C6 C24 -179.82(13) . . . . ? C10 C1 C6 C24 0.51(19) . . . . ? C2 C1 C6 C5 -0.24(19) . . . . ? C10 C1 C6 C5 -179.91(12) . . . . ? C2 C1 C10 C36 101.74(16) . . . 2_656 ? C6 C1 C10 C36 -78.59(16) . . . 2_656 ? C2 C1 C10 C31 -81.30(17) . . . . ? C6 C1 C10 C31 98.37(15) . . . . ? C4 C5 C21 C22 -178.88(15) . . . . ? C6 C5 C21 C22 0.7(2) . . . . ? C5 C21 C22 C23 -0.4(2) . . . . ? C21 C22 C23 C24 -0.3(2) . . . . ? C22 C23 C24 C6 0.6(2) . . . . ? C5 C6 C24 C23 -0.4(2) . . . . ? C1 C6 C24 C23 179.23(14) . . . . ? C36 C10 C31 C32 177.83(13) 2_656 . . . ? C1 C10 C31 C32 0.9(2) . . . . ? C36 C10 C31 C36 -1.04(18) 2_656 . . . ? C1 C10 C31 C36 -178.01(12) . . . . ? C10 C31 C32 C33 179.58(14) . . . . ? C36 C31 C32 C33 -1.5(2) . . . . ? C31 C32 C33 C34 -0.6(2) . . . . ? C32 C33 C34 C35 1.7(2) . . . . ? C33 C34 C35 C36 -0.5(2) . . . . ? C34 C35 C36 C10 177.13(14) . . . 2_656 ? C34 C35 C36 C31 -1.6(2) . . . . ? C10 C31 C36 C10 2.75(17) . . . 2_656 ? C32 C31 C36 C10 -176.16(13) . . . 2_656 ? C10 C31 C36 C35 -178.52(12) . . . . ? C32 C31 C36 C35 2.57(19) . . . . ? C46 C41 C42 C43 0.2(4) . . . . ? C41 C42 C43 C44 0.7(4) . . . . ? C42 C43 C44 C45 -1.3(3) . . . . ? C43 C44 C45 C46 1.0(3) . . . . ? C42 C41 C46 C45 -0.4(4) . . . . ? C44 C45 C46 C41 -0.2(3) . . . . ? _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.210 _refine_diff_density_min -0.185 _refine_diff_density_rms 0.038 _database_code_depnum_ccdc_archive 'CCDC 922265'