# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2011 ####################################################################### # # 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_wa758 _database_code_depnum_ccdc_archive 'CCDC 793257' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H21 B Li O2' _chemical_formula_sum 'C11 H21 B Li O2' _chemical_formula_weight 203.03 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 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 14.456(2) _cell_length_b 11.0059(11) _cell_length_c 16.369(2) _cell_angle_alpha 90.00 _cell_angle_beta 106.218(11) _cell_angle_gamma 90.00 _cell_volume 2500.7(5) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 5297 _cell_measurement_theta_min 3.8 _cell_measurement_theta_max 25.8 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.52 _exptl_crystal_size_mid 0.45 _exptl_crystal_size_min 0.38 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.079 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 888 _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 '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 5116 _diffrn_reflns_av_R_equivalents 0.0209 _diffrn_reflns_av_sigmaI/netI 0.0224 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.70 _diffrn_reflns_theta_max 25.66 _reflns_number_total 2300 _reflns_number_gt 1869 _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, 1990) ' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997) ' _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^)+(0.0948P)^2^+3.2115P] 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 0.0050(13) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2300 _refine_ls_number_parameters 158 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0759 _refine_ls_R_factor_gt 0.0642 _refine_ls_wR_factor_ref 0.1808 _refine_ls_wR_factor_gt 0.1711 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.052 _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 0.48342(16) 0.3816(2) 0.40834(14) 0.0289(5) Uani 1 1 d . . . H1A H 0.5154 0.4608 0.4130 0.043 Uiso 1 1 calc R . . H1B H 0.5133 0.3330 0.4590 0.043 Uiso 1 1 calc R . . H1C H 0.4149 0.3932 0.4037 0.043 Uiso 1 1 calc R . . C1 C 0.5000 0.3707(2) 0.2500 0.0233(6) Uani 1 2 d S . . H1 H 0.5000 0.4570 0.2500 0.028 Uiso 1 2 calc SR . . C2 C 0.49447(12) 0.31168(17) 0.32478(11) 0.0220(4) Uani 1 1 d . . . C3 C 0.49542(13) 0.18406(17) 0.32234(12) 0.0259(5) Uani 1 1 d . . . H3 H 0.4929 0.1397 0.3714 0.031 Uiso 1 1 calc R . . C4 C 0.5000 0.1209(3) 0.2500 0.0296(6) Uani 1 2 d S . . H4 H 0.5000 0.0346 0.2500 0.035 Uiso 1 2 calc SR . . Li1 Li 0.6031(2) 0.4461(3) 0.5407(2) 0.0321(8) Uani 1 1 d . . . O11 O 0.72376(10) 0.47750(15) 0.51308(10) 0.0403(5) Uani 1 1 d . . . C12 C 0.7703(6) 0.4020(5) 0.4690(7) 0.063(2) Uani 0.638(11) 1 d P A 1 H12A H 0.7235 0.3718 0.4166 0.076 Uiso 0.638(11) 1 calc PR A 1 H12B H 0.7979 0.3312 0.5048 0.076 Uiso 0.638(11) 1 calc PR A 1 C12' C 0.7369(8) 0.4417(14) 0.4288(7) 0.053(3) Uani 0.362(11) 1 d P A 2 H12C H 0.6971 0.4918 0.3818 0.064 Uiso 0.362(11) 1 calc PR A 2 H12D H 0.7226 0.3546 0.4162 0.064 Uiso 0.362(11) 1 calc PR A 2 C13 C 0.8480(2) 0.4701(3) 0.4465(2) 0.0658(9) Uani 1 1 d . . . H13A H 0.8278 0.4961 0.3862 0.079 Uiso 0.638(11) 1 calc PR A 1 H13B H 0.9073 0.4205 0.4565 0.079 Uiso 0.638(11) 1 calc PR A 1 H13C H 0.8877 0.4001 0.4739 0.079 Uiso 0.362(11) 1 calc PR A 2 H13D H 0.8641 0.4902 0.3930 0.079 Uiso 0.362(11) 1 calc PR A 2 C14 C 0.86360(18) 0.5774(3) 0.50498(19) 0.0523(7) Uani 1 1 d . A . H14A H 0.8868 0.6487 0.4795 0.063 Uiso 0.638(11) 1 calc PR A 1 H14B H 0.9103 0.5585 0.5604 0.063 Uiso 0.638(11) 1 calc PR A 1 H14C H 0.9309 0.5809 0.5414 0.063 Uiso 0.362(11) 1 calc PR A 2 H14D H 0.8478 0.6543 0.4728 0.063 Uiso 0.362(11) 1 calc PR A 2 C15 C 0.7615(4) 0.5995(4) 0.5147(4) 0.0383(13) Uani 0.638(11) 1 d P A 1 H15A H 0.7645 0.6406 0.5692 0.046 Uiso 0.638(11) 1 calc PR A 1 H15B H 0.7220 0.6488 0.4671 0.046 Uiso 0.638(11) 1 calc PR A 1 C15' C 0.7985(7) 0.5540(9) 0.5538(6) 0.043(3) Uani 0.362(11) 1 d P A 2 H15C H 0.8342 0.5169 0.6086 0.052 Uiso 0.362(11) 1 calc PR A 2 H15D H 0.7713 0.6320 0.5664 0.052 Uiso 0.362(11) 1 calc PR A 2 O21 O 0.64889(10) 0.33189(15) 0.63563(9) 0.0365(4) Uani 1 1 d . . . C22 C 0.58098(15) 0.2819(2) 0.67618(14) 0.0387(6) Uani 1 1 d . A . H22A H 0.5421 0.2175 0.6403 0.046 Uiso 1 1 calc R . . H22B H 0.5370 0.3461 0.6854 0.046 Uiso 1 1 calc R . . C23 C 0.6379(2) 0.2308(4) 0.7589(2) 0.0815(12) Uani 1 1 d . . . H23A H 0.6213 0.2726 0.8065 0.098 Uiso 1 1 calc R A . H23B H 0.6243 0.1430 0.7618 0.098 Uiso 1 1 calc R . . C24 C 0.7396(2) 0.2500(4) 0.7640(2) 0.0796(12) Uani 1 1 d . A . H24A H 0.7695 0.1734 0.7523 0.096 Uiso 1 1 calc R . . H24B H 0.7754 0.2795 0.8212 0.096 Uiso 1 1 calc R . . C25 C 0.74084(16) 0.3430(2) 0.69813(15) 0.0440(6) Uani 1 1 d . A . H25A H 0.7491 0.4254 0.7233 0.053 Uiso 1 1 calc R . . H25B H 0.7939 0.3269 0.6723 0.053 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 0.0306(11) 0.0374(12) 0.0200(10) -0.0028(9) 0.0090(8) -0.0057(9) C1 0.0253(12) 0.0229(13) 0.0219(13) 0.000 0.0070(10) 0.000 C2 0.0174(8) 0.0299(10) 0.0187(9) 0.0000(7) 0.0049(6) -0.0001(7) C3 0.0240(9) 0.0298(10) 0.0263(10) 0.0068(8) 0.0108(7) 0.0014(7) C4 0.0312(14) 0.0226(13) 0.0387(16) 0.000 0.0160(12) 0.000 Li1 0.0285(16) 0.043(2) 0.0260(17) 0.0036(14) 0.0093(13) -0.0014(14) O11 0.0361(8) 0.0464(10) 0.0455(10) -0.0075(7) 0.0232(7) -0.0076(7) C12 0.070(4) 0.043(3) 0.096(6) -0.018(3) 0.057(4) -0.007(2) C12' 0.056(6) 0.075(8) 0.041(5) -0.029(5) 0.032(4) -0.026(5) C13 0.0625(17) 0.0691(19) 0.084(2) -0.0120(17) 0.0498(16) -0.0033(15) C14 0.0420(13) 0.0581(16) 0.0626(17) -0.0038(13) 0.0243(12) -0.0129(12) C15 0.041(2) 0.038(2) 0.041(3) -0.0075(19) 0.020(2) -0.0052(18) C15' 0.043(4) 0.051(5) 0.036(4) -0.008(4) 0.013(4) -0.016(4) O21 0.0252(7) 0.0527(10) 0.0302(8) 0.0111(7) 0.0055(6) -0.0031(6) C22 0.0282(10) 0.0504(13) 0.0387(12) 0.0106(10) 0.0114(9) -0.0012(9) C23 0.0399(15) 0.135(3) 0.066(2) 0.059(2) 0.0100(13) -0.0024(17) C24 0.0404(14) 0.128(3) 0.0613(19) 0.049(2) -0.0011(13) -0.0096(16) C25 0.0309(11) 0.0596(15) 0.0361(12) 0.0086(11) 0.0005(9) -0.0088(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 B1 C2 1.616(3) . ? B1 H1A 0.9800 . ? B1 H1B 0.9800 . ? B1 H1C 0.9800 . ? C1 C2 1.408(2) 2_655 ? C1 C2 1.408(2) . ? C1 H1 0.9500 . ? C2 C3 1.405(3) . ? C3 C4 1.390(2) . ? C3 H3 0.9500 . ? C4 C3 1.390(2) 2_655 ? C4 H4 0.9500 . ? Li1 O11 1.952(4) . ? Li1 O21 1.964(4) . ? Li1 B1 2.537(4) 5_666 ? Li1 Li1 3.138(7) 5_666 ? O11 C15' 1.384(7) . ? O11 C12 1.391(6) . ? O11 C15 1.447(4) . ? O11 C12' 1.498(8) . ? C12 C13 1.480(7) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C12' C13 1.582(10) . ? C12' H12C 0.9900 . ? C12' H12D 0.9900 . ? C13 C14 1.497(4) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C13 H13C 0.9900 . ? C13 H13D 0.9900 . ? C14 C15' 1.418(7) . ? C14 C15 1.547(5) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C14 H14C 0.9900 . ? C14 H14D 0.9900 . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C15' H15C 0.9900 . ? C15' H15D 0.9900 . ? O21 C25 1.438(3) . ? O21 C22 1.439(3) . ? C22 C23 1.484(4) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C23 C24 1.465(4) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C24 C25 1.490(4) . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? C25 H25A 0.9900 . ? C25 H25B 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 C2 B1 H1A 109.5 . . ? C2 B1 H1B 109.5 . . ? H1A B1 H1B 109.5 . . ? C2 B1 H1C 109.5 . . ? H1A B1 H1C 109.5 . . ? H1B B1 H1C 109.5 . . ? C2 C1 C2 125.1(2) 2_655 . ? C2 C1 H1 117.5 2_655 . ? C2 C1 H1 117.5 . . ? C3 C2 C1 115.65(17) . . ? C3 C2 B1 120.27(17) . . ? C1 C2 B1 124.04(18) . . ? C4 C3 C2 121.79(18) . . ? C4 C3 H3 119.1 . . ? C2 C3 H3 119.1 . . ? C3 C4 C3 120.0(3) 2_655 . ? C3 C4 H4 120.0 2_655 . ? C3 C4 H4 120.0 . . ? O11 Li1 O21 99.84(16) . . ? O11 Li1 B1 119.89(18) . 5_666 ? O21 Li1 B1 107.87(16) . 5_666 ? O11 Li1 Li1 129.7(2) . 5_666 ? O21 Li1 Li1 130.4(2) . 5_666 ? B1 Li1 Li1 50.23(11) 5_666 5_666 ? C15' O11 C12 100.8(4) . . ? C12 O11 C15 109.2(3) . . ? C15' O11 C12' 108.7(5) . . ? C15 O11 C12' 96.7(5) . . ? C15' O11 Li1 128.6(3) . . ? C12 O11 Li1 127.4(3) . . ? C15 O11 Li1 121.1(2) . . ? C12' O11 Li1 121.3(4) . . ? O11 C12 C13 109.8(4) . . ? O11 C12 H12A 109.7 . . ? C13 C12 H12A 109.7 . . ? O11 C12 H12B 109.7 . . ? C13 C12 H12B 109.7 . . ? H12A C12 H12B 108.2 . . ? O11 C12' C13 99.4(5) . . ? O11 C12' H12C 111.9 . . ? C13 C12' H12C 111.9 . . ? O11 C12' H12D 111.9 . . ? C13 C12' H12D 111.9 . . ? H12C C12' H12D 109.6 . . ? C12 C13 C14 103.2(3) . . ? C14 C13 C12' 103.7(4) . . ? C12 C13 H13A 111.1 . . ? C14 C13 H13A 111.1 . . ? C12 C13 H13B 111.1 . . ? C14 C13 H13B 111.1 . . ? H13A C13 H13B 109.1 . . ? C14 C13 H13C 111.0 . . ? C12' C13 H13C 111.0 . . ? H13A C13 H13C 130.5 . . ? C14 C13 H13D 111.0 . . ? C12' C13 H13D 111.0 . . ? H13C C13 H13D 109.0 . . ? C15' C14 C13 102.3(4) . . ? C13 C14 C15 102.3(2) . . ? C13 C14 H14A 111.3 . . ? C15 C14 H14A 111.3 . . ? C13 C14 H14B 111.3 . . ? C15 C14 H14B 111.3 . . ? H14A C14 H14B 109.2 . . ? C15' C14 H14C 111.3 . . ? C13 C14 H14C 111.3 . . ? C15' C14 H14D 111.3 . . ? C13 C14 H14D 111.3 . . ? H14C C14 H14D 109.2 . . ? O11 C15 C14 102.6(3) . . ? O11 C15 H15A 111.2 . . ? C14 C15 H15A 111.2 . . ? O11 C15 H15B 111.2 . . ? C14 C15 H15B 111.2 . . ? H15A C15 H15B 109.2 . . ? O11 C15' C14 113.0(5) . . ? O11 C15' H15C 109.0 . . ? C14 C15' H15C 109.0 . . ? O11 C15' H15D 109.0 . . ? C14 C15' H15D 109.0 . . ? H15C C15' H15D 107.8 . . ? C25 O21 C22 108.56(16) . . ? C25 O21 Li1 123.29(17) . . ? C22 O21 Li1 119.12(16) . . ? O21 C22 C23 106.85(18) . . ? O21 C22 H22A 110.4 . . ? C23 C22 H22A 110.4 . . ? O21 C22 H22B 110.4 . . ? C23 C22 H22B 110.4 . . ? H22A C22 H22B 108.6 . . ? C24 C23 C22 106.8(2) . . ? C24 C23 H23A 110.4 . . ? C22 C23 H23A 110.4 . . ? C24 C23 H23B 110.4 . . ? C22 C23 H23B 110.4 . . ? H23A C23 H23B 108.6 . . ? C23 C24 C25 105.8(2) . . ? C23 C24 H24A 110.6 . . ? C25 C24 H24A 110.6 . . ? C23 C24 H24B 110.6 . . ? C25 C24 H24B 110.6 . . ? H24A C24 H24B 108.7 . . ? O21 C25 C24 105.13(19) . . ? O21 C25 H25A 110.7 . . ? C24 C25 H25A 110.7 . . ? O21 C25 H25B 110.7 . . ? C24 C25 H25B 110.7 . . ? H25A C25 H25B 108.8 . . ? 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 C2 C1 C2 C3 0.47(11) 2_655 . . . ? C2 C1 C2 B1 -177.16(18) 2_655 . . . ? C1 C2 C3 C4 -1.0(2) . . . . ? B1 C2 C3 C4 176.75(14) . . . . ? C2 C3 C4 C3 0.52(12) . . . 2_655 ? O21 Li1 O11 C15' -79.2(7) . . . . ? B1 Li1 O11 C15' 38.1(7) 5_666 . . . ? Li1 Li1 O11 C15' 99.3(8) 5_666 . . . ? O21 Li1 O11 C12 76.6(6) . . . . ? B1 Li1 O11 C12 -166.1(6) 5_666 . . . ? Li1 Li1 O11 C12 -104.9(6) 5_666 . . . ? O21 Li1 O11 C15 -122.1(3) . . . . ? B1 Li1 O11 C15 -4.8(4) 5_666 . . . ? Li1 Li1 O11 C15 56.4(4) 5_666 . . . ? O21 Li1 O11 C12' 116.1(8) . . . . ? B1 Li1 O11 C12' -126.6(8) 5_666 . . . ? Li1 Li1 O11 C12' -65.4(8) 5_666 . . . ? C15' O11 C12 C13 -30.6(7) . . . . ? C15 O11 C12 C13 5.3(7) . . . . ? C12' O11 C12 C13 77.2(9) . . . . ? Li1 O11 C12 C13 168.3(4) . . . . ? C15' O11 C12' C13 20.3(9) . . . . ? C12 O11 C12' C13 -60.5(8) . . . . ? C15 O11 C12' C13 54.8(7) . . . . ? Li1 O11 C12' C13 -172.3(4) . . . . ? O11 C12 C13 C14 17.9(8) . . . . ? O11 C12 C13 C12' -76.8(9) . . . . ? O11 C12' C13 C12 59.6(7) . . . . ? O11 C12' C13 C14 -33.3(9) . . . . ? C12 C13 C14 C15' 2.5(9) . . . . ? C12' C13 C14 C15' 34.4(10) . . . . ? C12 C13 C14 C15 -32.0(6) . . . . ? C12' C13 C14 C15 -0.1(8) . . . . ? C15' O11 C15 C14 56.2(6) . . . . ? C12 O11 C15 C14 -25.4(5) . . . . ? C12' O11 C15 C14 -56.7(5) . . . . ? Li1 O11 C15 C14 170.3(2) . . . . ? C15' C14 C15 O11 -58.5(6) . . . . ? C13 C14 C15 O11 35.3(4) . . . . ? C12 O11 C15' C14 33.9(8) . . . . ? C15 O11 C15' C14 -74.1(8) . . . . ? C12' O11 C15' C14 0.8(10) . . . . ? Li1 O11 C15' C14 -165.4(4) . . . . ? C13 C14 C15' O11 -23.0(10) . . . . ? C15 C14 C15' O11 70.8(8) . . . . ? O11 Li1 O21 C25 37.6(3) . . . . ? B1 Li1 O21 C25 -88.3(2) 5_666 . . . ? Li1 Li1 O21 C25 -140.9(3) 5_666 . . . ? O11 Li1 O21 C22 -179.09(17) . . . . ? B1 Li1 O21 C22 54.9(2) 5_666 . . . ? Li1 Li1 O21 C22 2.4(4) 5_666 . . . ? C25 O21 C22 C23 -15.2(3) . . . . ? Li1 O21 C22 C23 -163.4(3) . . . . ? O21 C22 C23 C24 -1.3(4) . . . . ? C22 C23 C24 C25 16.5(5) . . . . ? C22 O21 C25 C24 25.4(3) . . . . ? Li1 O21 C25 C24 172.0(2) . . . . ? C23 C24 C25 O21 -25.6(4) . . . . ? _diffrn_measured_fraction_theta_max 0.973 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.539 _refine_diff_density_min -0.303 _refine_diff_density_rms 0.050 data_wa787 _database_code_depnum_ccdc_archive 'CCDC 793258' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H42 B2 Li2 O4' _chemical_formula_sum 'C22 H42 B2 Li2 O4' _chemical_formula_weight 406.06 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 Triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.8448(8) _cell_length_b 9.0494(8) _cell_length_c 9.1349(9) _cell_angle_alpha 73.851(7) _cell_angle_beta 68.733(7) _cell_angle_gamma 66.814(7) _cell_volume 618.47(10) _cell_formula_units_Z 1 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 16361 _cell_measurement_theta_min 3.6 _cell_measurement_theta_max 27.6 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.37 _exptl_crystal_size_mid 0.33 _exptl_crystal_size_min 0.32 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.090 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 222 _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 14793 _diffrn_reflns_av_R_equivalents 0.0470 _diffrn_reflns_av_sigmaI/netI 0.0217 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 3.73 _diffrn_reflns_theta_max 25.03 _reflns_number_total 2176 _reflns_number_gt 1888 _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^)+(0.1027P)^2^+0.5383P] 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 2176 _refine_ls_number_parameters 147 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0755 _refine_ls_R_factor_gt 0.0679 _refine_ls_wR_factor_ref 0.1927 _refine_ls_wR_factor_gt 0.1865 _refine_ls_goodness_of_fit_ref 1.075 _refine_ls_restrained_S_all 1.075 _refine_ls_shift/su_max 0.002 _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 0.3263(3) 0.7000(3) 0.4419(3) 0.0212(5) Uani 1 1 d . . . H1A H 0.4251 0.7375 0.3826 0.032 Uiso 1 1 calc R . . H1B H 0.3159 0.6336 0.3799 0.032 Uiso 1 1 calc R . . H1C H 0.3425 0.6347 0.5438 0.032 Uiso 1 1 calc R . . C1 C 0.1529(2) 0.8562(2) 0.4741(2) 0.0183(5) Uani 1 1 d . . . C2 C 0.0675(3) 0.9084(3) 0.6228(3) 0.0252(5) Uani 1 1 d . . . H2 H 0.1105 0.8472 0.7106 0.030 Uiso 1 1 calc R . . C3 C -0.0784(3) 1.0467(3) 0.6470(3) 0.0252(5) Uani 1 1 d . . . H3 H -0.1293 1.0762 0.7503 0.030 Uiso 1 1 calc R . . Li1 Li 0.3908(4) 0.3978(4) 0.4965(4) 0.0246(8) Uani 1 1 d . . . O11 O 0.1897(2) 0.3566(2) 0.6606(2) 0.0339(5) Uani 1 1 d . . . C12 C 0.041(2) 0.4846(10) 0.7378(17) 0.057(4) Uani 0.49(3) 1 d P A 1 H12A H -0.0122 0.5680 0.6583 0.069 Uiso 0.49(3) 1 calc PR A 1 H12B H 0.0749 0.5381 0.7959 0.069 Uiso 0.49(3) 1 calc PR A 1 C12' C 0.0196(13) 0.449(2) 0.681(2) 0.076(5) Uani 0.51(3) 1 d P A 2 H12C H -0.0239 0.4291 0.6043 0.092 Uiso 0.51(3) 1 calc PR A 2 H12D H 0.0058 0.5657 0.6612 0.092 Uiso 0.51(3) 1 calc PR A 2 C13 C -0.0791(4) 0.3998(5) 0.8487(5) 0.0728(11) Uani 1 1 d . . . H13A H -0.1472 0.3828 0.7933 0.087 Uiso 0.49(3) 1 calc PR A 1 H13B H -0.1581 0.4611 0.9369 0.087 Uiso 0.49(3) 1 calc PR A 1 H13C H -0.1096 0.4829 0.9150 0.087 Uiso 0.51(3) 1 calc PR A 2 H13D H -0.1858 0.3864 0.8509 0.087 Uiso 0.51(3) 1 calc PR A 2 C14 C 0.0390(4) 0.2416(4) 0.9077(3) 0.0523(8) Uani 1 1 d . A . H14A H -0.0134 0.1546 0.9409 0.063 Uiso 1 1 calc R . . H14B H 0.0680 0.2514 0.9989 0.063 Uiso 1 1 calc R . . C15 C 0.1955(4) 0.2068(4) 0.7672(4) 0.0607(9) Uani 1 1 d . A . H15A H 0.3009 0.1637 0.8018 0.073 Uiso 1 1 calc R . . H15B H 0.1955 0.1250 0.7143 0.073 Uiso 1 1 calc R . . O21 O 0.4210(2) 0.2846(2) 0.32757(19) 0.0356(5) Uani 1 1 d . . . C22 C 0.3631(3) 0.1537(3) 0.3361(3) 0.0298(6) Uani 1 1 d . A . H22A H 0.2402 0.1773 0.3967 0.036 Uiso 1 1 calc R . . H22B H 0.4303 0.0503 0.3888 0.036 Uiso 1 1 calc R . . C23 C 0.3902(4) 0.1426(3) 0.1657(3) 0.0392(6) Uani 1 1 d . . . H23A H 0.2862 0.2103 0.1312 0.047 Uiso 1 1 calc R A . H23B H 0.4198 0.0286 0.1526 0.047 Uiso 1 1 calc R . . C24 C 0.5397(4) 0.2071(4) 0.0716(3) 0.0477(7) Uani 1 1 d . A . H24A H 0.6501 0.1166 0.0541 0.057 Uiso 1 1 calc R . . H24B H 0.5250 0.2697 -0.0329 0.057 Uiso 1 1 calc R . . C25 C 0.5340(4) 0.3149(4) 0.1732(3) 0.0453(7) Uani 1 1 d . A . H25A H 0.6504 0.2909 0.1809 0.054 Uiso 1 1 calc R . . H25B H 0.4918 0.4306 0.1259 0.054 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 0.0174(11) 0.0169(11) 0.0261(12) -0.0046(9) -0.0058(9) -0.0022(9) C1 0.0140(9) 0.0147(9) 0.0266(11) -0.0044(8) -0.0050(8) -0.0049(7) C2 0.0238(11) 0.0232(11) 0.0234(11) -0.0023(8) -0.0106(8) 0.0001(9) C3 0.0224(11) 0.0255(11) 0.0222(11) -0.0089(8) -0.0053(8) 0.0004(9) Li1 0.0232(17) 0.0229(17) 0.0280(18) -0.0068(14) -0.0060(14) -0.0072(14) O11 0.0248(9) 0.0315(9) 0.0360(9) -0.0017(7) 0.0000(7) -0.0100(7) C12 0.044(6) 0.027(3) 0.057(6) -0.010(3) 0.022(4) 0.002(3) C12' 0.027(3) 0.080(10) 0.083(9) 0.028(7) -0.014(5) -0.008(5) C13 0.0425(18) 0.069(2) 0.070(2) -0.0120(18) 0.0121(16) -0.0055(16) C14 0.0485(17) 0.069(2) 0.0336(14) 0.0053(13) -0.0064(12) -0.0273(15) C15 0.0471(17) 0.0396(16) 0.069(2) 0.0056(15) 0.0002(15) -0.0119(14) O21 0.0500(11) 0.0397(10) 0.0258(9) -0.0127(7) 0.0011(7) -0.0292(9) C22 0.0373(13) 0.0253(11) 0.0321(12) -0.0078(9) -0.0094(10) -0.0139(10) C23 0.0529(16) 0.0367(13) 0.0360(14) -0.0138(11) -0.0161(12) -0.0145(12) C24 0.071(2) 0.0407(15) 0.0277(13) -0.0117(11) -0.0013(13) -0.0218(14) C25 0.0470(16) 0.0666(19) 0.0295(13) -0.0157(12) 0.0025(11) -0.0325(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag B1 C1 1.622(3) . ? B1 H1A 0.9800 . ? B1 H1B 0.9800 . ? B1 H1C 0.9800 . ? C1 C3 1.401(3) 2_576 ? C1 C2 1.403(3) . ? C2 C3 1.398(3) . ? C2 H2 0.9500 . ? C3 C1 1.401(3) 2_576 ? C3 H3 0.9500 . ? Li1 O11 1.956(4) . ? Li1 O21 1.967(4) . ? Li1 B1 2.522(4) 2_666 ? Li1 Li1 3.182(7) 2_666 ? O11 C12' 1.374(11) . ? O11 C15 1.427(3) . ? O11 C12 1.467(8) . ? C12 C13 1.473(12) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C12' C13 1.507(14) . ? C12' H12C 0.9900 . ? C12' H12D 0.9900 . ? C13 C14 1.494(5) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C13 H13C 0.9900 . ? C13 H13D 0.9900 . ? C14 C15 1.502(4) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? O21 C25 1.428(3) . ? O21 C22 1.438(3) . ? C22 C23 1.513(3) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C23 C24 1.527(4) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C24 C25 1.499(4) . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? C25 H25A 0.9900 . ? C25 H25B 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 C1 B1 H1A 109.5 . . ? C1 B1 H1B 109.5 . . ? H1A B1 H1B 109.5 . . ? C1 B1 H1C 109.5 . . ? H1A B1 H1C 109.5 . . ? H1B B1 H1C 109.5 . . ? C3 C1 C2 114.26(18) 2_576 . ? C3 C1 B1 122.22(18) 2_576 . ? C2 C1 B1 123.50(18) . . ? C3 C2 C1 122.69(19) . . ? C3 C2 H2 118.7 . . ? C1 C2 H2 118.7 . . ? C2 C3 C1 123.1(2) . 2_576 ? C2 C3 H3 118.5 . . ? C1 C3 H3 118.5 2_576 . ? O11 Li1 O21 102.82(17) . . ? O11 Li1 B1 119.87(18) . 2_666 ? O21 Li1 B1 107.87(16) . 2_666 ? O11 Li1 Li1 128.1(2) . 2_666 ? O21 Li1 Li1 129.1(2) . 2_666 ? B1 Li1 Li1 50.49(11) 2_666 2_666 ? C12' O11 C15 107.2(5) . . ? C15 O11 C12 107.5(5) . . ? C12' O11 Li1 128.4(5) . . ? C15 O11 Li1 123.69(19) . . ? C12 O11 Li1 123.6(4) . . ? O11 C12 C13 105.0(6) . . ? O11 C12 H12A 110.8 . . ? C13 C12 H12A 110.8 . . ? O11 C12 H12B 110.8 . . ? C13 C12 H12B 110.8 . . ? H12A C12 H12B 108.8 . . ? O11 C12' C13 108.0(7) . . ? O11 C12' H12C 110.1 . . ? C13 C12' H12C 110.1 . . ? O11 C12' H12D 110.1 . . ? C13 C12' H12D 110.1 . . ? H12C C12' H12D 108.4 . . ? C12 C13 C14 102.5(7) . . ? C14 C13 C12' 105.2(6) . . ? C12 C13 H13A 111.3 . . ? C14 C13 H13A 111.3 . . ? C12 C13 H13B 111.3 . . ? C14 C13 H13B 111.3 . . ? C12' C13 H13B 133.5 . . ? H13A C13 H13B 109.2 . . ? C14 C13 H13C 110.7 . . ? C12' C13 H13C 110.7 . . ? C14 C13 H13D 110.7 . . ? C12' C13 H13D 110.7 . . ? H13C C13 H13D 108.8 . . ? C13 C14 C15 104.0(2) . . ? C13 C14 H14A 111.0 . . ? C15 C14 H14A 111.0 . . ? C13 C14 H14B 111.0 . . ? C15 C14 H14B 111.0 . . ? H14A C14 H14B 109.0 . . ? O11 C15 C14 107.2(2) . . ? O11 C15 H15A 110.3 . . ? C14 C15 H15A 110.3 . . ? O11 C15 H15B 110.3 . . ? C14 C15 H15B 110.3 . . ? H15A C15 H15B 108.5 . . ? C25 O21 C22 110.14(18) . . ? C25 O21 Li1 119.31(18) . . ? C22 O21 Li1 130.02(17) . . ? O21 C22 C23 105.77(19) . . ? O21 C22 H22A 110.6 . . ? C23 C22 H22A 110.6 . . ? O21 C22 H22B 110.6 . . ? C23 C22 H22B 110.6 . . ? H22A C22 H22B 108.7 . . ? C22 C23 C24 103.7(2) . . ? C22 C23 H23A 111.0 . . ? C24 C23 H23A 111.0 . . ? C22 C23 H23B 111.0 . . ? C24 C23 H23B 111.0 . . ? H23A C23 H23B 109.0 . . ? C25 C24 C23 104.7(2) . . ? C25 C24 H24A 110.8 . . ? C23 C24 H24A 110.8 . . ? C25 C24 H24B 110.8 . . ? C23 C24 H24B 110.8 . . ? H24A C24 H24B 108.9 . . ? O21 C25 C24 108.0(2) . . ? O21 C25 H25A 110.1 . . ? C24 C25 H25A 110.1 . . ? O21 C25 H25B 110.1 . . ? C24 C25 H25B 110.1 . . ? H25A C25 H25B 108.4 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C3 C1 C2 C3 -0.7(3) 2_576 . . . ? B1 C1 C2 C3 177.66(19) . . . . ? C1 C2 C3 C1 0.8(4) . . . 2_576 ? O21 Li1 O11 C12' -90.5(15) . . . . ? B1 Li1 O11 C12' 149.9(15) 2_666 . . . ? Li1 Li1 O11 C12' 88.7(15) 2_666 . . . ? O21 Li1 O11 C15 78.6(3) . . . . ? B1 Li1 O11 C15 -41.0(3) 2_666 . . . ? Li1 Li1 O11 C15 -102.2(3) 2_666 . . . ? O21 Li1 O11 C12 -130.2(11) . . . . ? B1 Li1 O11 C12 110.2(11) 2_666 . . . ? Li1 Li1 O11 C12 49.0(11) 2_666 . . . ? C12' O11 C12 C13 68.7(14) . . . . ? C15 O11 C12 C13 -26.1(14) . . . . ? Li1 O11 C12 C13 178.8(6) . . . . ? C15 O11 C12' C13 28.0(18) . . . . ? C12 O11 C12' C13 -67.6(15) . . . . ? Li1 O11 C12' C13 -161.4(6) . . . . ? O11 C12 C13 C14 36.9(13) . . . . ? O11 C12 C13 C12' -62.0(10) . . . . ? O11 C12' C13 C12 73.2(11) . . . . ? O11 C12' C13 C14 -15.7(18) . . . . ? C12 C13 C14 C15 -33.8(8) . . . . ? C12' C13 C14 C15 -2.1(11) . . . . ? C12' O11 C15 C14 -29.5(12) . . . . ? C12 O11 C15 C14 4.3(10) . . . . ? Li1 O11 C15 C14 159.4(2) . . . . ? C13 C14 C15 O11 18.6(4) . . . . ? O11 Li1 O21 C25 167.0(2) . . . . ? B1 Li1 O21 C25 -65.4(3) 2_666 . . . ? Li1 Li1 O21 C25 -12.3(4) 2_666 . . . ? O11 Li1 O21 C22 -22.2(3) . . . . ? B1 Li1 O21 C22 105.4(2) 2_666 . . . ? Li1 Li1 O21 C22 158.6(2) 2_666 . . . ? C25 O21 C22 C23 -20.5(3) . . . . ? Li1 O21 C22 C23 168.0(2) . . . . ? O21 C22 C23 C24 27.6(3) . . . . ? C22 C23 C24 C25 -24.6(3) . . . . ? C22 O21 C25 C24 4.5(3) . . . . ? Li1 O21 C25 C24 177.1(2) . . . . ? C23 C24 C25 O21 13.1(3) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.687 _refine_diff_density_min -0.404 _refine_diff_density_rms 0.059 data_wa981 _database_code_depnum_ccdc_archive 'CCDC 793259' # start Validation Reply Form _vrf_PLAT222_wa981 ; PROBLEM: Large Non-Solvent H Ueq(max)/Ueq(min) ... 5.38 Ratio RESPONSE: This atom belongs to a disordered terminal group of a hexyl chain. ; # end Validation Reply Form _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H54 B2 N2' _chemical_formula_sum 'C26 H54 B2 N2' _chemical_formula_weight 416.33 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' N N 0.0061 0.0033 '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 10.3561(10) _cell_length_b 10.8699(6) _cell_length_c 12.2614(10) _cell_angle_alpha 90.00 _cell_angle_beta 94.386(7) _cell_angle_gamma 90.00 _cell_volume 1376.22(19) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 10528 _cell_measurement_theta_min 3.3 _cell_measurement_theta_max 26.8 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.005 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 468 _exptl_absorpt_coefficient_mu 0.056 _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 13090 _diffrn_reflns_av_R_equivalents 0.0479 _diffrn_reflns_av_sigmaI/netI 0.0331 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.27 _diffrn_reflns_theta_max 26.40 _reflns_number_total 2800 _reflns_number_gt 2208 _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, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0813P)^2^+0.1124P] 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 2800 _refine_ls_number_parameters 163 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0653 _refine_ls_R_factor_gt 0.0495 _refine_ls_wR_factor_ref 0.1302 _refine_ls_wR_factor_gt 0.1231 _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_restrained_S_all 1.029 _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 N1 N 0.55258(11) 0.18676(9) 0.33742(9) 0.0236(3) Uani 1 1 d . . . B1 B 0.58499(14) 0.23265(13) 0.46495(12) 0.0224(3) Uani 1 1 d . . . H1A H 0.5370 0.1804 0.5142 0.027 Uiso 1 1 calc R . . H1B H 0.6787 0.2222 0.4854 0.027 Uiso 1 1 calc R . . C1 C 0.54558(12) 0.37561(10) 0.48181(9) 0.0194(3) Uani 1 1 d . . . C2 C 0.41719(12) 0.40410(11) 0.50139(10) 0.0200(3) Uani 1 1 d . . . H2 H 0.3578 0.3376 0.5032 0.024 Uiso 1 1 calc R . . C3 C 0.36941(12) 0.52262(11) 0.51847(9) 0.0199(3) Uani 1 1 d . . . C4 C 0.22603(12) 0.53629(12) 0.53328(11) 0.0246(3) Uani 1 1 d . . . H4A H 0.2141 0.6050 0.5845 0.030 Uiso 1 1 calc R . . H4B H 0.1950 0.4603 0.5673 0.030 Uiso 1 1 calc R . . C5 C 0.14206(13) 0.56050(12) 0.42669(12) 0.0272(3) Uani 1 1 d . B . H5A H 0.0543 0.5847 0.4454 0.033 Uiso 1 1 calc R . . H5B H 0.1793 0.6309 0.3885 0.033 Uiso 1 1 calc R . . C6 C 0.12990(14) 0.45192(13) 0.34857(12) 0.0321(3) Uani 1 1 d D . . H6A H 0.1000 0.3783 0.3870 0.039 Uiso 0.50 1 calc PR A 1 H6B H 0.2152 0.4331 0.3211 0.039 Uiso 0.50 1 calc PR A 1 H6C H 0.2186 0.4268 0.3331 0.039 Uiso 0.50 1 calc PR A 2 H6D H 0.0919 0.3827 0.3877 0.039 Uiso 0.50 1 calc PR A 2 C7 C 0.0279(10) 0.4864(12) 0.2485(9) 0.0303(15) Uani 0.50 1 d PD B 1 H7A H -0.0528 0.5173 0.2773 0.036 Uiso 0.50 1 calc PR B 1 H7B H 0.0640 0.5529 0.2048 0.036 Uiso 0.50 1 calc PR B 1 C8 C -0.0036(4) 0.3747(4) 0.1749(4) 0.0365(10) Uani 0.50 1 d PD B 1 H8A H -0.0804 0.3936 0.1247 0.044 Uiso 0.50 1 calc PR B 1 H8B H -0.0256 0.3041 0.2210 0.044 Uiso 0.50 1 calc PR B 1 C9 C 0.1119(4) 0.3375(4) 0.1057(4) 0.0436(10) Uani 0.50 1 d PD B 1 H9A H 0.0871 0.2658 0.0605 0.065 Uiso 0.50 1 calc PR B 1 H9B H 0.1879 0.3173 0.1550 0.065 Uiso 0.50 1 calc PR B 1 H9C H 0.1327 0.4064 0.0585 0.065 Uiso 0.50 1 calc PR B 1 C7' C 0.0550(11) 0.4661(12) 0.2444(11) 0.043(2) Uani 0.50 1 d PD B 2 H7'1 H 0.0829 0.5429 0.2097 0.052 Uiso 0.50 1 calc PR B 2 H7'2 H -0.0372 0.4763 0.2587 0.052 Uiso 0.50 1 calc PR B 2 C8' C 0.0655(8) 0.3568(4) 0.1602(5) 0.0660(18) Uani 0.50 1 d PD B 2 H8'1 H 0.1583 0.3403 0.1517 0.079 Uiso 0.50 1 calc PR B 2 H8'2 H 0.0281 0.2818 0.1911 0.079 Uiso 0.50 1 calc PR B 2 C9' C -0.0008(6) 0.3802(5) 0.0503(4) 0.0862(17) Uani 0.50 1 d PD B 2 H9'1 H 0.0172 0.3124 0.0010 0.129 Uiso 0.50 1 calc PR B 2 H9'2 H 0.0311 0.4574 0.0210 0.129 Uiso 0.50 1 calc PR B 2 H9'3 H -0.0944 0.3863 0.0564 0.129 Uiso 0.50 1 calc PR B 2 C10 C 0.63040(16) 0.25981(13) 0.26380(12) 0.0334(3) Uani 1 1 d . . . H10A H 0.6065 0.3468 0.2680 0.050 Uiso 1 1 calc R . . H10B H 0.6134 0.2307 0.1884 0.050 Uiso 1 1 calc R . . H10C H 0.7227 0.2501 0.2864 0.050 Uiso 1 1 calc R . . C11 C 0.59195(16) 0.05539(12) 0.32790(13) 0.0350(4) Uani 1 1 d . . . H11A H 0.5420 0.0045 0.3755 0.052 Uiso 1 1 calc R . . H11B H 0.6845 0.0471 0.3500 0.052 Uiso 1 1 calc R . . H11C H 0.5753 0.0282 0.2519 0.052 Uiso 1 1 calc R . . C12 C 0.41341(14) 0.20065(13) 0.29551(12) 0.0339(4) Uani 1 1 d . . . H12A H 0.4059 0.1812 0.2164 0.041 Uiso 1 1 calc R . . H12B H 0.3883 0.2879 0.3035 0.041 Uiso 1 1 calc R . . C13 C 0.31813(16) 0.12134(16) 0.35112(17) 0.0491(5) Uani 1 1 d . . . H13A H 0.2304 0.1367 0.3182 0.074 Uiso 1 1 calc R . . H13B H 0.3221 0.1415 0.4292 0.074 Uiso 1 1 calc R . . H13C H 0.3401 0.0344 0.3420 0.074 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 N1 0.0295(6) 0.0183(5) 0.0231(6) -0.0036(4) 0.0027(4) 0.0030(4) B1 0.0267(7) 0.0210(6) 0.0195(7) 0.0003(5) 0.0013(5) 0.0017(5) C1 0.0244(6) 0.0204(6) 0.0134(5) 0.0002(4) 0.0010(4) 0.0003(4) C2 0.0229(6) 0.0193(5) 0.0178(6) -0.0010(4) 0.0014(5) -0.0035(4) C3 0.0218(6) 0.0226(6) 0.0154(6) -0.0013(5) 0.0018(4) 0.0000(5) C4 0.0232(7) 0.0254(6) 0.0260(7) -0.0029(5) 0.0064(5) -0.0004(5) C5 0.0200(6) 0.0280(6) 0.0339(7) 0.0007(5) 0.0035(5) 0.0008(5) C6 0.0318(8) 0.0332(7) 0.0312(8) -0.0008(6) 0.0011(6) -0.0050(6) C7 0.023(3) 0.042(4) 0.025(2) -0.003(2) -0.0073(18) 0.003(2) C8 0.0210(16) 0.053(2) 0.0349(18) -0.0104(15) 0.0002(16) -0.0104(16) C9 0.043(2) 0.053(2) 0.035(2) -0.0276(18) 0.0060(16) -0.0061(15) C7' 0.038(5) 0.039(4) 0.051(4) 0.012(3) -0.007(3) -0.002(3) C8' 0.099(5) 0.039(2) 0.054(4) 0.010(2) -0.038(4) -0.026(3) C9' 0.113(5) 0.080(3) 0.061(3) 0.003(2) -0.021(3) -0.017(3) C10 0.0484(9) 0.0310(7) 0.0218(7) -0.0024(5) 0.0084(6) -0.0011(6) C11 0.0443(9) 0.0207(7) 0.0403(8) -0.0084(6) 0.0054(6) 0.0059(6) C12 0.0341(8) 0.0363(7) 0.0301(8) -0.0123(6) -0.0062(6) 0.0058(6) C13 0.0342(9) 0.0426(9) 0.0702(13) -0.0228(8) 0.0033(8) -0.0064(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 N1 C10 1.4853(18) . ? N1 C11 1.4921(16) . ? N1 C12 1.5002(18) . ? N1 B1 1.6513(17) . ? B1 C1 1.6239(17) . ? B1 H1A 0.9900 . ? B1 H1B 0.9900 . ? C1 C2 1.4037(18) . ? C1 C3 1.4139(17) 3_666 ? C2 C3 1.4016(17) . ? C2 H2 0.9500 . ? C3 C1 1.4138(17) 3_666 ? C3 C4 1.5170(17) . ? C4 C5 1.5361(19) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.519(2) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7' 1.451(13) . ? C6 C7 1.601(10) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C6 H6C 0.9900 . ? C6 H6D 0.9900 . ? C7 C8 1.532(13) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.571(5) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C7' C8' 1.584(13) . ? C7' H7'1 0.9900 . ? C7' H7'2 0.9900 . ? C8' C9' 1.487(6) . ? C8' H8'1 0.9900 . ? C8' H8'2 0.9900 . ? C9' H9'1 0.9800 . ? C9' H9'2 0.9800 . ? C9' H9'3 0.9800 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 C13 1.511(2) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 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 C10 N1 C11 107.45(11) . . ? C10 N1 C12 106.85(11) . . ? C11 N1 C12 109.31(11) . . ? C10 N1 B1 109.48(10) . . ? C11 N1 B1 109.04(10) . . ? C12 N1 B1 114.47(10) . . ? C1 B1 N1 112.01(10) . . ? C1 B1 H1A 109.2 . . ? N1 B1 H1A 109.2 . . ? C1 B1 H1B 109.2 . . ? N1 B1 H1B 109.2 . . ? H1A B1 H1B 107.9 . . ? C2 C1 C3 115.21(11) . 3_666 ? C2 C1 B1 118.91(11) . . ? C3 C1 B1 125.86(11) 3_666 . ? C3 C2 C1 125.32(11) . . ? C3 C2 H2 117.3 . . ? C1 C2 H2 117.3 . . ? C2 C3 C1 119.46(11) . 3_666 ? C2 C3 C4 117.89(11) . . ? C1 C3 C4 122.62(11) 3_666 . ? C3 C4 C5 114.24(11) . . ? C3 C4 H4A 108.7 . . ? C5 C4 H4A 108.7 . . ? C3 C4 H4B 108.7 . . ? C5 C4 H4B 108.7 . . ? H4A C4 H4B 107.6 . . ? C6 C5 C4 114.68(11) . . ? C6 C5 H5A 108.6 . . ? C4 C5 H5A 108.6 . . ? C6 C5 H5B 108.6 . . ? C4 C5 H5B 108.6 . . ? H5A C5 H5B 107.6 . . ? C7' C6 C5 119.0(5) . . ? C5 C6 C7 108.6(4) . . ? C7' C6 H6A 109.8 . . ? C5 C6 H6A 110.0 . . ? C7 C6 H6A 110.0 . . ? C5 C6 H6B 110.0 . . ? C7 C6 H6B 110.0 . . ? H6A C6 H6B 108.3 . . ? C7' C6 H6C 107.6 . . ? C5 C6 H6C 107.6 . . ? C7 C6 H6C 119.0 . . ? H6A C6 H6C 101.4 . . ? C7' C6 H6D 107.6 . . ? C5 C6 H6D 107.6 . . ? H6C C6 H6D 107.0 . . ? C8 C7 C6 111.4(7) . . ? C8 C7 H7A 109.4 . . ? C6 C7 H7A 109.4 . . ? C8 C7 H7B 109.4 . . ? C6 C7 H7B 109.4 . . ? H7A C7 H7B 108.0 . . ? C7 C8 C9 112.7(5) . . ? C7 C8 H8A 109.1 . . ? C9 C8 H8A 109.1 . . ? C7 C8 H8B 109.1 . . ? C9 C8 H8B 109.1 . . ? H8A C8 H8B 107.8 . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C6 C7' C8' 115.8(7) . . ? C6 C7' H7'1 108.3 . . ? C8' C7' H7'1 108.3 . . ? C6 C7' H7'2 108.3 . . ? C8' C7' H7'2 108.3 . . ? H7'1 C7' H7'2 107.4 . . ? C9' C8' C7' 114.3(6) . . ? C9' C8' H8'1 108.7 . . ? C7' C8' H8'1 108.7 . . ? C9' C8' H8'2 108.7 . . ? C7' C8' H8'2 108.7 . . ? H8'1 C8' H8'2 107.6 . . ? C8' C9' H9'1 109.5 . . ? C8' C9' H9'2 109.5 . . ? H9'1 C9' H9'2 109.5 . . ? C8' C9' H9'3 109.5 . . ? H9'1 C9' H9'3 109.5 . . ? H9'2 C9' H9'3 109.5 . . ? N1 C10 H10A 109.5 . . ? N1 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? N1 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? N1 C11 H11A 109.5 . . ? N1 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? N1 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? N1 C12 C13 115.55(13) . . ? N1 C12 H12A 108.4 . . ? C13 C12 H12A 108.4 . . ? N1 C12 H12B 108.4 . . ? C13 C12 H12B 108.4 . . ? H12A C12 H12B 107.5 . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 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 C10 N1 B1 C1 62.33(14) . . . . ? C11 N1 B1 C1 179.62(11) . . . . ? C12 N1 B1 C1 -57.60(14) . . . . ? N1 B1 C1 C2 84.41(14) . . . . ? N1 B1 C1 C3 -97.35(14) . . . 3_666 ? C3 C1 C2 C3 0.93(19) 3_666 . . . ? B1 C1 C2 C3 179.36(11) . . . . ? C1 C2 C3 C1 -1.0(2) . . . 3_666 ? C1 C2 C3 C4 177.25(11) . . . . ? C2 C3 C4 C5 -91.54(14) . . . . ? C1 C3 C4 C5 86.62(14) 3_666 . . . ? C3 C4 C5 C6 69.64(15) . . . . ? C4 C5 C6 C7' -178.6(6) . . . . ? C4 C5 C6 C7 173.8(5) . . . . ? C7' C6 C7 C8 40(5) . . . . ? C5 C6 C7 C8 -171.9(6) . . . . ? C6 C7 C8 C9 -71.6(9) . . . . ? C5 C6 C7' C8' 170.5(7) . . . . ? C7 C6 C7' C8' -154(6) . . . . ? C6 C7' C8' C9' -173.7(8) . . . . ? C10 N1 C12 C13 173.17(12) . . . . ? C11 N1 C12 C13 57.18(16) . . . . ? B1 N1 C12 C13 -65.45(15) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.264 _refine_diff_density_min -0.234 _refine_diff_density_rms 0.045 data_wa1024 _database_code_depnum_ccdc_archive 'CCDC 793260' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C34 H56 B2' _chemical_formula_sum 'C34 H56 B2' _chemical_formula_weight 486.41 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 12.5723(11) _cell_length_b 9.5902(6) _cell_length_c 13.5233(11) _cell_angle_alpha 90.00 _cell_angle_beta 108.187(6) _cell_angle_gamma 90.00 _cell_volume 1549.1(2) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 7583 _cell_measurement_theta_min 2.7 _cell_measurement_theta_max 26.9 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.33 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.043 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 540 _exptl_absorpt_coefficient_mu 0.057 _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 10470 _diffrn_reflns_av_R_equivalents 0.0647 _diffrn_reflns_av_sigmaI/netI 0.0493 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.65 _diffrn_reflns_theta_max 25.03 _reflns_number_total 2727 _reflns_number_gt 1961 _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^)+(0.0936P)^2^+0.1350P] 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 2727 _refine_ls_number_parameters 162 _refine_ls_number_restraints 8 _refine_ls_R_factor_all 0.0795 _refine_ls_R_factor_gt 0.0579 _refine_ls_wR_factor_ref 0.1646 _refine_ls_wR_factor_gt 0.1540 _refine_ls_goodness_of_fit_ref 1.070 _refine_ls_restrained_S_all 1.108 _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 0.38352(19) 0.7834(2) 0.58764(16) 0.0313(5) Uani 1 1 d . . . C1 C 0.43981(16) 0.90327(19) 0.54262(13) 0.0277(4) Uani 1 1 d . . . C2 C 0.55287(16) 0.88379(19) 0.54958(13) 0.0292(4) Uani 1 1 d . . . H2 H 0.5901 0.8034 0.5849 0.035 Uiso 1 1 calc R . . C3 C 0.61327(16) 0.9753(2) 0.50771(14) 0.0292(4) Uani 1 1 d . . . C4 C 0.73103(17) 0.9366(2) 0.51085(16) 0.0361(5) Uani 1 1 d . . . H4A H 0.7568 0.8563 0.5583 0.043 Uiso 1 1 calc R . . H4B H 0.7817 1.0160 0.5392 0.043 Uiso 1 1 calc R . . C5 C 0.73843(17) 0.8990(2) 0.40386(17) 0.0378(5) Uani 1 1 d . . . H5A H 0.6815 0.8269 0.3727 0.045 Uiso 1 1 calc R . . H5B H 0.7196 0.9826 0.3588 0.045 Uiso 1 1 calc R . . C6 C 0.8520(2) 0.8455(3) 0.4041(2) 0.0539(6) Uani 1 1 d D A . H6A H 0.9087 0.9186 0.4332 0.065 Uiso 1 1 calc R . . H6B H 0.8719 0.7633 0.4505 0.065 Uiso 1 1 calc R . . C7 C 0.8573(2) 0.8049(4) 0.2979(3) 0.0867(12) Uani 1 1 d D . . H7A H 0.8114 0.7193 0.2787 0.104 Uiso 0.508(7) 1 calc PR A 1 H7B H 0.8162 0.8787 0.2500 0.104 Uiso 0.508(7) 1 calc PR A 1 H7C H 0.8522 0.8880 0.2533 0.104 Uiso 0.492(7) 1 calc PR A 2 H7D H 0.7962 0.7395 0.2630 0.104 Uiso 0.492(7) 1 calc PR A 2 C8 C 0.9588(4) 0.7784(6) 0.2689(5) 0.0581(16) Uiso 0.508(7) 1 d PD A 1 H8A H 1.0196 0.8438 0.3045 0.070 Uiso 0.508(7) 1 calc PR A 1 H8B H 0.9436 0.7855 0.1928 0.070 Uiso 0.508(7) 1 calc PR A 1 C9 C 0.9874(5) 0.6305(6) 0.3067(5) 0.0687(19) Uiso 0.508(7) 1 d PD A 1 H9A H 0.9278 0.5930 0.3315 0.103 Uiso 0.508(7) 1 calc PR A 1 H9B H 1.0583 0.6298 0.3637 0.103 Uiso 0.508(7) 1 calc PR A 1 H9C H 0.9945 0.5728 0.2493 0.103 Uiso 0.508(7) 1 calc PR A 1 C8' C 0.9799(4) 0.7296(6) 0.3231(4) 0.0538(16) Uiso 0.492(7) 1 d PD A 2 H8C H 1.0398 0.7990 0.3520 0.065 Uiso 0.492(7) 1 calc PR A 2 H8D H 0.9872 0.6554 0.3757 0.065 Uiso 0.492(7) 1 calc PR A 2 C9' C 0.9929(6) 0.6680(7) 0.2263(5) 0.073(2) Uiso 0.492(7) 1 d PD A 2 H9D H 0.9936 0.5660 0.2315 0.110 Uiso 0.492(7) 1 calc PR A 2 H9E H 1.0634 0.7001 0.2175 0.110 Uiso 0.492(7) 1 calc PR A 2 H9F H 0.9302 0.6973 0.1663 0.110 Uiso 0.492(7) 1 calc PR A 2 C11 C 0.27038(18) 0.7072(2) 0.53001(16) 0.0408(5) Uani 1 1 d . . . H11 H 0.2301 0.7597 0.4653 0.049 Uiso 1 1 calc R . . C12 C 0.1945(2) 0.6957(3) 0.60006(19) 0.0533(6) Uani 1 1 d . . . H12A H 0.1592 0.7877 0.6013 0.064 Uiso 1 1 calc R . . H12B H 0.1338 0.6286 0.5677 0.064 Uiso 1 1 calc R . . C13 C 0.2523(2) 0.6499(3) 0.71279(19) 0.0530(6) Uani 1 1 d . . . H13A H 0.2040 0.6754 0.7554 0.064 Uiso 1 1 calc R . . H13B H 0.2599 0.5471 0.7146 0.064 Uiso 1 1 calc R . . C14 C 0.3678(2) 0.7143(2) 0.76165(16) 0.0449(6) Uani 1 1 d . . . H14A H 0.4051 0.6654 0.8279 0.054 Uiso 1 1 calc R . . H14B H 0.3581 0.8129 0.7786 0.054 Uiso 1 1 calc R . . C15 C 0.44524(18) 0.7089(2) 0.69318(15) 0.0347(5) Uani 1 1 d . . . H15 H 0.5159 0.7605 0.7289 0.042 Uiso 1 1 calc R . . C16 C 0.4748(2) 0.5591(2) 0.66840(18) 0.0459(6) Uani 1 1 d . . . H16A H 0.5390 0.5642 0.6408 0.055 Uiso 1 1 calc R . . H16B H 0.4997 0.5058 0.7343 0.055 Uiso 1 1 calc R . . C17 C 0.3811(2) 0.4779(3) 0.5911(2) 0.0557(7) Uani 1 1 d . . . H17A H 0.3317 0.4382 0.6284 0.067 Uiso 1 1 calc R . . H17B H 0.4144 0.3992 0.5636 0.067 Uiso 1 1 calc R . . C18 C 0.3103(2) 0.5645(3) 0.50000(18) 0.0555(7) Uani 1 1 d . . . H18A H 0.2436 0.5093 0.4617 0.067 Uiso 1 1 calc R . . H18B H 0.3543 0.5817 0.4519 0.067 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 0.0415(12) 0.0286(12) 0.0272(10) -0.0009(8) 0.0153(9) 0.0016(9) C1 0.0367(10) 0.0270(10) 0.0197(8) -0.0007(7) 0.0090(7) 0.0000(7) C2 0.0390(11) 0.0245(10) 0.0233(9) 0.0017(7) 0.0084(8) 0.0037(8) C3 0.0351(10) 0.0305(11) 0.0214(9) 0.0007(7) 0.0081(7) 0.0016(8) C4 0.0359(11) 0.0364(11) 0.0361(11) 0.0060(9) 0.0110(8) 0.0041(8) C5 0.0358(11) 0.0376(12) 0.0440(12) -0.0015(9) 0.0182(9) 0.0000(9) C6 0.0387(12) 0.0585(16) 0.0694(16) -0.0122(13) 0.0239(12) 0.0011(11) C7 0.0594(17) 0.113(3) 0.107(3) -0.064(2) 0.0538(18) -0.0318(17) C11 0.0469(12) 0.0403(13) 0.0327(10) 0.0061(9) 0.0087(9) -0.0081(9) C12 0.0470(13) 0.0632(17) 0.0503(14) 0.0060(12) 0.0158(11) -0.0126(11) C13 0.0637(16) 0.0573(16) 0.0472(13) 0.0050(11) 0.0308(12) -0.0084(12) C14 0.0653(15) 0.0433(13) 0.0294(10) 0.0029(9) 0.0197(10) -0.0056(10) C15 0.0454(12) 0.0286(11) 0.0290(10) 0.0034(8) 0.0099(9) -0.0042(8) C16 0.0619(15) 0.0312(12) 0.0447(12) 0.0050(9) 0.0169(11) 0.0029(10) C17 0.0812(18) 0.0350(13) 0.0529(14) -0.0074(10) 0.0236(13) -0.0045(11) C18 0.0789(18) 0.0482(15) 0.0375(12) -0.0102(10) 0.0155(12) -0.0145(12) _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 C15 1.568(3) . ? B1 C1 1.569(3) . ? B1 C11 1.573(3) . ? C1 C2 1.407(3) . ? C1 C3 1.407(3) 3_676 ? C2 C3 1.391(3) . ? C2 H2 0.9500 . ? C3 C1 1.407(3) 3_676 ? C3 C4 1.514(3) . ? C4 C5 1.522(3) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.517(3) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.508(4) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.469(5) . ? C7 C8' 1.639(5) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C7 H7C 0.9900 . ? C7 H7D 0.9900 . ? C8 C9 1.512(7) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C8' C9' 1.491(7) . ? C8' H8C 0.9900 . ? C8' H8D 0.9900 . ? C9' H9D 0.9800 . ? C9' H9E 0.9800 . ? C9' H9F 0.9800 . ? C11 C12 1.544(3) . ? C11 C18 1.554(3) . ? C11 H11 1.0000 . ? C12 C13 1.534(3) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.525(3) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C15 1.540(3) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 C16 1.546(3) . ? C15 H15 1.0000 . ? C16 C17 1.522(3) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 C18 1.522(4) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 H18A 0.9900 . ? C18 H18B 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 C15 B1 C1 122.15(18) . . ? C15 B1 C11 110.70(17) . . ? C1 B1 C11 126.58(17) . . ? C2 C1 C3 117.30(17) . 3_676 ? C2 C1 B1 116.43(16) . . ? C3 C1 B1 126.20(18) 3_676 . ? C3 C2 C1 123.86(17) . . ? C3 C2 H2 118.1 . . ? C1 C2 H2 118.1 . . ? C2 C3 C1 118.82(18) . 3_676 ? C2 C3 C4 119.15(17) . . ? C1 C3 C4 121.89(17) 3_676 . ? C3 C4 C5 112.39(17) . . ? C3 C4 H4A 109.1 . . ? C5 C4 H4A 109.1 . . ? C3 C4 H4B 109.1 . . ? C5 C4 H4B 109.1 . . ? H4A C4 H4B 107.9 . . ? C6 C5 C4 114.55(19) . . ? C6 C5 H5A 108.6 . . ? C4 C5 H5A 108.6 . . ? C6 C5 H5B 108.6 . . ? C4 C5 H5B 108.6 . . ? H5A C5 H5B 107.6 . . ? C7 C6 C5 114.0(2) . . ? C7 C6 H6A 108.7 . . ? C5 C6 H6A 108.7 . . ? C7 C6 H6B 108.7 . . ? C5 C6 H6B 108.7 . . ? H6A C6 H6B 107.6 . . ? C8 C7 C6 126.8(3) . . ? C6 C7 C8' 103.6(3) . . ? C8 C7 H7A 105.6 . . ? C6 C7 H7A 105.6 . . ? C8 C7 H7B 105.6 . . ? C6 C7 H7B 105.6 . . ? H7A C7 H7B 106.1 . . ? C6 C7 H7C 111.0 . . ? C8' C7 H7C 111.0 . . ? C8 C7 H7D 111.8 . . ? C6 C7 H7D 111.0 . . ? C8' C7 H7D 111.0 . . ? H7C C7 H7D 109.0 . . ? C7 C8 C9 102.0(4) . . ? C7 C8 H8A 111.4 . . ? C9 C8 H8A 111.4 . . ? C7 C8 H8B 111.4 . . ? C9 C8 H8B 111.4 . . ? H8A C8 H8B 109.2 . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C9' C8' C7 110.2(4) . . ? C9' C8' H8C 109.6 . . ? C7 C8' H8C 109.6 . . ? C9' C8' H8D 109.6 . . ? C7 C8' H8D 109.6 . . ? H8C C8' H8D 108.1 . . ? C8' C9' H9D 109.5 . . ? C8' C9' H9E 109.5 . . ? H9D C9' H9E 109.5 . . ? C8' C9' H9F 109.5 . . ? H9D C9' H9F 109.5 . . ? H9E C9' H9F 109.5 . . ? C12 C11 C18 114.16(19) . . ? C12 C11 B1 111.43(18) . . ? C18 C11 B1 102.86(18) . . ? C12 C11 H11 109.4 . . ? C18 C11 H11 109.4 . . ? B1 C11 H11 109.4 . . ? C13 C12 C11 116.0(2) . . ? C13 C12 H12A 108.3 . . ? C11 C12 H12A 108.3 . . ? C13 C12 H12B 108.3 . . ? C11 C12 H12B 108.3 . . ? H12A C12 H12B 107.4 . . ? C14 C13 C12 113.95(18) . . ? C14 C13 H13A 108.8 . . ? C12 C13 H13A 108.8 . . ? C14 C13 H13B 108.8 . . ? C12 C13 H13B 108.8 . . ? H13A C13 H13B 107.7 . . ? C13 C14 C15 114.88(18) . . ? C13 C14 H14A 108.5 . . ? C15 C14 H14A 108.5 . . ? C13 C14 H14B 108.5 . . ? C15 C14 H14B 108.5 . . ? H14A C14 H14B 107.5 . . ? C14 C15 C16 113.66(17) . . ? C14 C15 B1 107.80(17) . . ? C16 C15 B1 108.06(17) . . ? C14 C15 H15 109.1 . . ? C16 C15 H15 109.1 . . ? B1 C15 H15 109.1 . . ? C17 C16 C15 115.9(2) . . ? C17 C16 H16A 108.3 . . ? C15 C16 H16A 108.3 . . ? C17 C16 H16B 108.3 . . ? C15 C16 H16B 108.3 . . ? H16A C16 H16B 107.4 . . ? C16 C17 C18 114.1(2) . . ? C16 C17 H17A 108.7 . . ? C18 C17 H17A 108.7 . . ? C16 C17 H17B 108.7 . . ? C18 C17 H17B 108.7 . . ? H17A C17 H17B 107.6 . . ? C17 C18 C11 115.07(19) . . ? C17 C18 H18A 108.5 . . ? C11 C18 H18A 108.5 . . ? C17 C18 H18B 108.5 . . ? C11 C18 H18B 108.5 . . ? H18A C18 H18B 107.5 . . ? 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 C15 B1 C1 C2 42.3(2) . . . . ? C11 B1 C1 C2 -128.2(2) . . . . ? C15 B1 C1 C3 -140.6(2) . . . 3_676 ? C11 B1 C1 C3 48.9(3) . . . 3_676 ? C3 C1 C2 C3 -1.6(3) 3_676 . . . ? B1 C1 C2 C3 175.76(17) . . . . ? C1 C2 C3 C1 1.6(3) . . . 3_676 ? C1 C2 C3 C4 -174.11(17) . . . . ? C2 C3 C4 C5 108.4(2) . . . . ? C1 C3 C4 C5 -67.2(2) 3_676 . . . ? C3 C4 C5 C6 -174.17(18) . . . . ? C4 C5 C6 C7 178.4(2) . . . . ? C5 C6 C7 C8 166.1(4) . . . . ? C5 C6 C7 C8' -171.5(3) . . . . ? C6 C7 C8 C9 80.7(5) . . . . ? C8' C7 C8 C9 34.0(5) . . . . ? C8 C7 C8' C9' -43.5(6) . . . . ? C6 C7 C8' C9' 173.4(4) . . . . ? C15 B1 C11 C12 55.3(2) . . . . ? C1 B1 C11 C12 -133.3(2) . . . . ? C15 B1 C11 C18 -67.4(2) . . . . ? C1 B1 C11 C18 104.0(2) . . . . ? C18 C11 C12 C13 71.3(3) . . . . ? B1 C11 C12 C13 -44.7(3) . . . . ? C11 C12 C13 C14 40.2(3) . . . . ? C12 C13 C14 C15 -46.9(3) . . . . ? C13 C14 C15 C16 -62.9(3) . . . . ? C13 C14 C15 B1 56.9(2) . . . . ? C1 B1 C15 C14 127.64(19) . . . . ? C11 B1 C15 C14 -60.5(2) . . . . ? C1 B1 C15 C16 -109.1(2) . . . . ? C11 B1 C15 C16 62.7(2) . . . . ? C14 C15 C16 C17 72.7(2) . . . . ? B1 C15 C16 C17 -46.9(2) . . . . ? C15 C16 C17 C18 39.9(3) . . . . ? C16 C17 C18 C11 -47.5(3) . . . . ? C12 C11 C18 C17 -61.7(3) . . . . ? B1 C11 C18 C17 59.2(2) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.259 _refine_diff_density_min -0.271 _refine_diff_density_rms 0.042 data_wa780 _database_code_depnum_ccdc_archive 'CCDC 793266' #TrackingRef 'publ.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H28 B2 O4' _chemical_formula_sum 'C18 H28 B2 O4' _chemical_formula_weight 330.02 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.3824(8) _cell_length_b 9.8427(9) _cell_length_c 12.8041(12) _cell_angle_alpha 102.329(7) _cell_angle_beta 96.038(8) _cell_angle_gamma 110.013(7) _cell_volume 951.26(15) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 14669 _cell_measurement_theta_min 3.9 _cell_measurement_theta_max 25.4 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.152 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 356 _exptl_absorpt_coefficient_mu 0.077 _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 14687 _diffrn_reflns_av_R_equivalents 0.0378 _diffrn_reflns_av_sigmaI/netI 0.0267 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.82 _diffrn_reflns_theta_max 25.55 _reflns_number_total 3545 _reflns_number_gt 2922 _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, 1990) ' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997) ' _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^)+(0.0495P)^2^+0.2211P] 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 0.037(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3545 _refine_ls_number_parameters 218 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0494 _refine_ls_R_factor_gt 0.0385 _refine_ls_wR_factor_ref 0.0973 _refine_ls_wR_factor_gt 0.0928 _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_restrained_S_all 1.024 _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 0.40796(18) 0.25976(16) 0.59948(12) 0.0227(3) Uani 1 1 d . . . O1 O 0.29679(12) 0.30451(10) 0.54243(7) 0.0269(2) Uani 1 1 d . . . O2 O 0.46902(13) 0.34248(10) 0.70567(8) 0.0294(2) Uani 1 1 d . . . C1 C 0.25870(17) 0.41613(15) 0.62118(11) 0.0265(3) Uani 1 1 d . . . C2 C 0.41676(18) 0.47279(15) 0.71793(11) 0.0272(3) Uani 1 1 d . . . C11 C 0.2433(2) 0.53468(18) 0.56575(14) 0.0422(4) Uani 1 1 d . . . H11A H 0.3554 0.5883 0.5488 0.063 Uiso 1 1 calc R . . H11B H 0.2083 0.6059 0.6145 0.063 Uiso 1 1 calc R . . H11C H 0.1564 0.4861 0.4982 0.063 Uiso 1 1 calc R . . C12 C 0.0852(2) 0.33254(19) 0.64844(15) 0.0452(4) Uani 1 1 d . . . H12A H 0.0960 0.2564 0.6840 0.068 Uiso 1 1 calc R . . H12B H -0.0025 0.2838 0.5812 0.068 Uiso 1 1 calc R . . H12C H 0.0505 0.4037 0.6976 0.068 Uiso 1 1 calc R . . C21 C 0.3746(2) 0.50824(19) 0.83111(13) 0.0430(4) Uani 1 1 d . . . H21A H 0.2752 0.4236 0.8372 0.065 Uiso 1 1 calc R . . H21B H 0.3465 0.5985 0.8426 0.065 Uiso 1 1 calc R . . H21C H 0.4748 0.5254 0.8862 0.065 Uiso 1 1 calc R . . C22 C 0.57091(19) 0.60262(17) 0.70646(15) 0.0404(4) Uani 1 1 d . . . H22A H 0.5959 0.5784 0.6332 0.061 Uiso 1 1 calc R . . H22B H 0.6721 0.6196 0.7608 0.061 Uiso 1 1 calc R . . H22C H 0.5440 0.6934 0.7180 0.061 Uiso 1 1 calc R . . C31 C 0.45805(16) 0.12462(14) 0.54704(10) 0.0220(3) Uani 1 1 d . . . C32 C 0.60163(17) 0.10300(15) 0.59640(11) 0.0255(3) Uani 1 1 d . . . H32 H 0.6720 0.1729 0.6623 0.031 Uiso 1 1 calc R . . C33 C 0.64249(17) -0.01913(15) 0.55038(11) 0.0259(3) Uani 1 1 d . . . H33 H 0.7403 -0.0315 0.5855 0.031 Uiso 1 1 calc R . . B1A B 0.09753(18) 0.75944(16) 0.90186(12) 0.0229(3) Uani 1 1 d . . . O1A O 0.23088(12) 0.89322(10) 0.95239(7) 0.0271(2) Uani 1 1 d . . . O2A O 0.01856(12) 0.75489(10) 0.80108(8) 0.0274(2) Uani 1 1 d . . . C1A C 0.26376(17) 0.97996(14) 0.87103(10) 0.0250(3) Uani 1 1 d . . . C2A C 0.08552(17) 0.90917(14) 0.78961(11) 0.0242(3) Uani 1 1 d . . . C11A C 0.3201(2) 1.14531(16) 0.92897(13) 0.0395(4) Uani 1 1 d . . . H11D H 0.2252 1.1629 0.9607 0.059 Uiso 1 1 calc R . . H11E H 0.3503 1.2050 0.8766 0.059 Uiso 1 1 calc R . . H11F H 0.4211 1.1747 0.9870 0.059 Uiso 1 1 calc R . . C12A C 0.41041(18) 0.95186(18) 0.82116(12) 0.0341(3) Uani 1 1 d . . . H12D H 0.3735 0.8451 0.7839 0.051 Uiso 1 1 calc R . . H12E H 0.5118 0.9811 0.8788 0.051 Uiso 1 1 calc R . . H12F H 0.4404 1.0113 0.7687 0.051 Uiso 1 1 calc R . . C21A C 0.09597(19) 0.90136(16) 0.67068(11) 0.0306(3) Uani 1 1 d . . . H21D H 0.1793 0.8560 0.6499 0.046 Uiso 1 1 calc R . . H21E H 0.1335 1.0028 0.6607 0.046 Uiso 1 1 calc R . . H21F H -0.0182 0.8402 0.6248 0.046 Uiso 1 1 calc R . . C22A C -0.0444(2) 0.97923(18) 0.82275(13) 0.0358(3) Uani 1 1 d . . . H22D H -0.0508 0.9836 0.8993 0.054 Uiso 1 1 calc R . . H22E H -0.1587 0.9182 0.7769 0.054 Uiso 1 1 calc R . . H22F H -0.0072 1.0810 0.8133 0.054 Uiso 1 1 calc R . . C31A C 0.04431(16) 0.62400(14) 0.95387(10) 0.0232(3) Uani 1 1 d . . . C32A C -0.09731(17) 0.49029(15) 0.90176(11) 0.0255(3) Uani 1 1 d . . . H32A H -0.1647 0.4826 0.8347 0.031 Uiso 1 1 calc R . . C33A C -0.14013(17) 0.36880(15) 0.94709(11) 0.0262(3) Uani 1 1 d . . . H33A H -0.2361 0.2794 0.9102 0.031 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 0.0231(7) 0.0202(7) 0.0270(7) 0.0080(6) 0.0091(6) 0.0086(6) O1 0.0296(5) 0.0258(5) 0.0276(5) 0.0025(4) 0.0044(4) 0.0165(4) O2 0.0393(6) 0.0250(5) 0.0286(5) 0.0034(4) 0.0031(4) 0.0209(4) C1 0.0253(7) 0.0225(7) 0.0332(7) 0.0025(6) 0.0075(5) 0.0133(5) C2 0.0318(7) 0.0205(7) 0.0321(7) 0.0036(5) 0.0048(6) 0.0156(6) C11 0.0484(9) 0.0375(9) 0.0466(9) 0.0082(7) 0.0002(7) 0.0278(8) C12 0.0299(8) 0.0406(9) 0.0587(11) 0.0011(8) 0.0164(7) 0.0106(7) C21 0.0658(11) 0.0379(9) 0.0320(8) 0.0019(7) 0.0098(7) 0.0319(8) C22 0.0286(8) 0.0248(8) 0.0625(11) 0.0043(7) 0.0033(7) 0.0096(6) C31 0.0251(6) 0.0198(6) 0.0255(6) 0.0089(5) 0.0108(5) 0.0101(5) C32 0.0265(7) 0.0241(7) 0.0238(6) 0.0026(5) 0.0040(5) 0.0096(5) C33 0.0258(7) 0.0276(7) 0.0279(7) 0.0077(5) 0.0047(5) 0.0145(6) B1A 0.0233(7) 0.0218(7) 0.0255(7) 0.0093(6) 0.0072(6) 0.0084(6) O1A 0.0331(5) 0.0224(5) 0.0225(5) 0.0114(4) 0.0035(4) 0.0036(4) O2A 0.0283(5) 0.0191(5) 0.0309(5) 0.0123(4) 0.0003(4) 0.0024(4) C1A 0.0310(7) 0.0204(7) 0.0229(6) 0.0118(5) 0.0053(5) 0.0051(5) C2A 0.0285(7) 0.0175(6) 0.0271(7) 0.0114(5) 0.0053(5) 0.0059(5) C11A 0.0522(10) 0.0213(7) 0.0354(8) 0.0083(6) 0.0029(7) 0.0033(7) C12A 0.0276(7) 0.0376(8) 0.0372(8) 0.0174(7) 0.0066(6) 0.0080(6) C21A 0.0377(8) 0.0299(7) 0.0258(7) 0.0116(6) 0.0040(6) 0.0130(6) C22A 0.0387(8) 0.0386(8) 0.0414(8) 0.0213(7) 0.0145(7) 0.0198(7) C31A 0.0242(6) 0.0225(7) 0.0272(7) 0.0114(5) 0.0099(5) 0.0098(5) C32A 0.0254(7) 0.0260(7) 0.0263(7) 0.0119(5) 0.0046(5) 0.0083(5) C33A 0.0247(7) 0.0215(7) 0.0296(7) 0.0094(5) 0.0053(5) 0.0039(5) _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 O2 1.3672(17) . ? B1 O1 1.3679(17) . ? B1 C31 1.5674(19) . ? O1 C1 1.4698(15) . ? O2 C2 1.4746(16) . ? C1 C11 1.523(2) . ? C1 C12 1.525(2) . ? C1 C2 1.5668(19) . ? C2 C22 1.521(2) . ? C2 C21 1.524(2) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C31 C32 1.4021(18) . ? C31 C33 1.4039(19) 2_656 ? C32 C33 1.3897(18) . ? C32 H32 0.9500 . ? C33 C31 1.4039(19) 2_656 ? C33 H33 0.9500 . ? B1A O1A 1.3706(17) . ? B1A O2A 1.3713(17) . ? B1A C31A 1.5667(19) . ? O1A C1A 1.4729(15) . ? O2A C2A 1.4737(15) . ? C1A C11A 1.5188(19) . ? C1A C12A 1.522(2) . ? C1A C2A 1.5666(18) . ? C2A C21A 1.5216(18) . ? C2A C22A 1.5259(19) . ? C11A H11D 0.9800 . ? C11A H11E 0.9800 . ? C11A H11F 0.9800 . ? C12A H12D 0.9800 . ? C12A H12E 0.9800 . ? C12A H12F 0.9800 . ? C21A H21D 0.9800 . ? C21A H21E 0.9800 . ? C21A H21F 0.9800 . ? C22A H22D 0.9800 . ? C22A H22E 0.9800 . ? C22A H22F 0.9800 . ? C31A C33A 1.4023(19) 2_567 ? C31A C32A 1.4055(19) . ? C32A C33A 1.3937(18) . ? C32A H32A 0.9500 . ? C33A C31A 1.4023(19) 2_567 ? C33A H33A 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 B1 O1 113.88(11) . . ? O2 B1 C31 123.61(12) . . ? O1 B1 C31 122.51(12) . . ? B1 O1 C1 107.19(10) . . ? B1 O2 C2 106.88(10) . . ? O1 C1 C11 107.91(11) . . ? O1 C1 C12 106.34(11) . . ? C11 C1 C12 109.93(13) . . ? O1 C1 C2 102.34(9) . . ? C11 C1 C2 115.10(12) . . ? C12 C1 C2 114.38(13) . . ? O2 C2 C22 106.67(11) . . ? O2 C2 C21 108.19(11) . . ? C22 C2 C21 110.46(13) . . ? O2 C2 C1 102.28(10) . . ? C22 C2 C1 113.45(12) . . ? C21 C2 C1 115.01(12) . . ? C1 C11 H11A 109.5 . . ? C1 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C1 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C1 C12 H12A 109.5 . . ? C1 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C1 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C2 C21 H21A 109.5 . . ? C2 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C2 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C2 C22 H22A 109.5 . . ? C2 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C2 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C32 C31 C33 117.80(12) . 2_656 ? C32 C31 B1 121.51(12) . . ? C33 C31 B1 120.68(12) 2_656 . ? C33 C32 C31 120.98(12) . . ? C33 C32 H32 119.5 . . ? C31 C32 H32 119.5 . . ? C32 C33 C31 121.22(12) . 2_656 ? C32 C33 H33 119.4 . . ? C31 C33 H33 119.4 2_656 . ? O1A B1A O2A 113.61(11) . . ? O1A B1A C31A 122.79(12) . . ? O2A B1A C31A 123.58(12) . . ? B1A O1A C1A 106.87(10) . . ? B1A O2A C2A 106.84(10) . . ? O1A C1A C11A 108.57(11) . . ? O1A C1A C12A 106.66(11) . . ? C11A C1A C12A 109.76(12) . . ? O1A C1A C2A 102.09(10) . . ? C11A C1A C2A 115.57(12) . . ? C12A C1A C2A 113.44(11) . . ? O2A C2A C21A 108.41(10) . . ? O2A C2A C22A 106.78(10) . . ? C21A C2A C22A 109.92(11) . . ? O2A C2A C1A 101.96(10) . . ? C21A C2A C1A 115.29(11) . . ? C22A C2A C1A 113.71(11) . . ? C1A C11A H11D 109.5 . . ? C1A C11A H11E 109.5 . . ? H11D C11A H11E 109.5 . . ? C1A C11A H11F 109.5 . . ? H11D C11A H11F 109.5 . . ? H11E C11A H11F 109.5 . . ? C1A C12A H12D 109.5 . . ? C1A C12A H12E 109.5 . . ? H12D C12A H12E 109.5 . . ? C1A C12A H12F 109.5 . . ? H12D C12A H12F 109.5 . . ? H12E C12A H12F 109.5 . . ? C2A C21A H21D 109.5 . . ? C2A C21A H21E 109.5 . . ? H21D C21A H21E 109.5 . . ? C2A C21A H21F 109.5 . . ? H21D C21A H21F 109.5 . . ? H21E C21A H21F 109.5 . . ? C2A C22A H22D 109.5 . . ? C2A C22A H22E 109.5 . . ? H22D C22A H22E 109.5 . . ? C2A C22A H22F 109.5 . . ? H22D C22A H22F 109.5 . . ? H22E C22A H22F 109.5 . . ? C33A C31A C32A 117.87(12) 2_567 . ? C33A C31A B1A 120.74(12) 2_567 . ? C32A C31A B1A 121.36(12) . . ? C33A C32A C31A 120.87(13) . . ? C33A C32A H32A 119.6 . . ? C31A C32A H32A 119.6 . . ? C32A C33A C31A 121.26(12) . 2_567 ? C32A C33A H33A 119.4 . . ? C31A C33A H33A 119.4 2_567 . ? 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 B1 O1 C1 -8.46(15) . . . . ? C31 B1 O1 C1 170.94(12) . . . . ? O1 B1 O2 C2 -10.07(15) . . . . ? C31 B1 O2 C2 170.54(12) . . . . ? B1 O1 C1 C11 143.59(12) . . . . ? B1 O1 C1 C12 -98.51(13) . . . . ? B1 O1 C1 C2 21.79(13) . . . . ? B1 O2 C2 C22 -96.71(13) . . . . ? B1 O2 C2 C21 144.45(12) . . . . ? B1 O2 C2 C1 22.65(13) . . . . ? O1 C1 C2 O2 -26.65(12) . . . . ? C11 C1 C2 O2 -143.39(12) . . . . ? C12 C1 C2 O2 87.89(13) . . . . ? O1 C1 C2 C22 87.84(13) . . . . ? C11 C1 C2 C22 -28.91(16) . . . . ? C12 C1 C2 C22 -157.62(12) . . . . ? O1 C1 C2 C21 -143.64(12) . . . . ? C11 C1 C2 C21 99.61(15) . . . . ? C12 C1 C2 C21 -29.11(17) . . . . ? O2 B1 C31 C32 -16.6(2) . . . . ? O1 B1 C31 C32 164.03(12) . . . . ? O2 B1 C31 C33 162.05(12) . . . 2_656 ? O1 B1 C31 C33 -17.29(19) . . . 2_656 ? C33 C31 C32 C33 -0.2(2) 2_656 . . . ? B1 C31 C32 C33 178.55(12) . . . . ? C31 C32 C33 C31 0.2(2) . . . 2_656 ? O2A B1A O1A C1A -9.62(15) . . . . ? C31A B1A O1A C1A 169.02(12) . . . . ? O1A B1A O2A C2A -10.29(15) . . . . ? C31A B1A O2A C2A 171.08(11) . . . . ? B1A O1A C1A C11A 146.26(12) . . . . ? B1A O1A C1A C12A -95.52(12) . . . . ? B1A O1A C1A C2A 23.74(13) . . . . ? B1A O2A C2A C21A 146.14(11) . . . . ? B1A O2A C2A C22A -95.47(12) . . . . ? B1A O2A C2A C1A 24.08(12) . . . . ? O1A C1A C2A O2A -28.68(12) . . . . ? C11A C1A C2A O2A -146.30(11) . . . . ? C12A C1A C2A O2A 85.68(12) . . . . ? O1A C1A C2A C21A -145.89(11) . . . . ? C11A C1A C2A C21A 96.50(14) . . . . ? C12A C1A C2A C21A -31.52(16) . . . . ? O1A C1A C2A C22A 85.86(12) . . . . ? C11A C1A C2A C22A -31.75(16) . . . . ? C12A C1A C2A C22A -159.77(12) . . . . ? O1A B1A C31A C33A -4.25(19) . . . 2_567 ? O2A B1A C31A C33A 174.26(12) . . . 2_567 ? O1A B1A C31A C32A 177.54(12) . . . . ? O2A B1A C31A C32A -3.9(2) . . . . ? C33A C31A C32A C33A -0.3(2) 2_567 . . . ? B1A C31A C32A C33A 177.94(12) . . . . ? C31A C32A C33A C31A 0.3(2) . . . 2_567 ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.234 _refine_diff_density_min -0.156 _refine_diff_density_rms 0.035 data_wa1063 _database_code_depnum_ccdc_archive 'CCDC 793267' #TrackingRef 'publ.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H28 Br2' _chemical_formula_sum 'C18 H28 Br2' _chemical_formula_weight 404.22 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' Br Br -0.2901 2.4595 '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 6.6943(6) _cell_length_b 7.8948(8) _cell_length_c 9.8024(9) _cell_angle_alpha 109.190(7) _cell_angle_beta 99.292(7) _cell_angle_gamma 108.450(7) _cell_volume 443.27(7) _cell_formula_units_Z 1 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 6617 _cell_measurement_theta_min 3.4 _cell_measurement_theta_max 26.8 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.514 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 206 _exptl_absorpt_coefficient_mu 4.563 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3950 _exptl_absorpt_correction_T_max 0.5885 _exptl_absorpt_process_details 'MULABS (Spek, 2003; Blessing, 1995)' _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 7617 _diffrn_reflns_av_R_equivalents 0.0594 _diffrn_reflns_av_sigmaI/netI 0.0351 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.36 _diffrn_reflns_theta_max 26.36 _reflns_number_total 1798 _reflns_number_gt 1746 _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^)+(0.0366P)^2^+0.0690P] 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 0.057(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1798 _refine_ls_number_parameters 92 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0257 _refine_ls_R_factor_gt 0.0243 _refine_ls_wR_factor_ref 0.0597 _refine_ls_wR_factor_gt 0.0592 _refine_ls_goodness_of_fit_ref 1.077 _refine_ls_restrained_S_all 1.077 _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 Br1 Br -0.09138(3) -0.01473(3) 0.813674(18) 0.02707(11) Uani 1 1 d . . . C1 C -0.0433(3) -0.0103(3) 0.6288(2) 0.0201(3) Uani 1 1 d . . . C2 C 0.1703(3) 0.0967(3) 0.6341(2) 0.0216(3) Uani 1 1 d . . . H2 H 0.2839 0.1624 0.7278 0.026 Uiso 1 1 calc R . . C3 C 0.2196(3) 0.1087(2) 0.5041(2) 0.0199(3) Uani 1 1 d . . . C4 C 0.4501(3) 0.2239(3) 0.5054(2) 0.0227(4) Uani 1 1 d . . . H4A H 0.4432 0.3236 0.4667 0.027 Uiso 1 1 calc R . . H4B H 0.4974 0.1337 0.4343 0.027 Uiso 1 1 calc R . . C5 C 0.6258(3) 0.3263(3) 0.6588(2) 0.0231(4) Uani 1 1 d . . . H5A H 0.6343 0.2281 0.6990 0.028 Uiso 1 1 calc R . . H5B H 0.5826 0.4197 0.7304 0.028 Uiso 1 1 calc R . . C6 C 0.8530(3) 0.4359(3) 0.6490(2) 0.0236(4) Uani 1 1 d . . . H6A H 0.8940 0.3436 0.5746 0.028 Uiso 1 1 calc R . . H6B H 0.8464 0.5378 0.6128 0.028 Uiso 1 1 calc R . . C7 C 1.0290(3) 0.5310(3) 0.8020(2) 0.0244(4) Uani 1 1 d . . . H7A H 0.9843 0.6197 0.8765 0.029 Uiso 1 1 calc R . . H7B H 1.0365 0.4280 0.8365 0.029 Uiso 1 1 calc R . . C8 C 1.2577(3) 0.6466(3) 0.7991(2) 0.0282(4) Uani 1 1 d . . . H8A H 1.2541 0.7564 0.7726 0.034 Uiso 1 1 calc R . . H8B H 1.2994 0.5609 0.7201 0.034 Uiso 1 1 calc R . . C9 C 1.4305(3) 0.7266(3) 0.9513(3) 0.0350(4) Uani 1 1 d . . . H9A H 1.5750 0.7999 0.9454 0.053 Uiso 1 1 calc R . . H9B H 1.4365 0.6180 0.9770 0.053 Uiso 1 1 calc R . . H9C H 1.3911 0.8133 1.0295 0.053 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 Br1 0.02605(13) 0.03447(16) 0.01920(14) 0.01194(10) 0.00796(8) 0.00845(9) C1 0.0222(8) 0.0209(8) 0.0175(8) 0.0077(7) 0.0072(6) 0.0084(6) C2 0.0194(7) 0.0202(8) 0.0200(8) 0.0056(7) 0.0024(6) 0.0055(6) C3 0.0181(7) 0.0180(8) 0.0220(9) 0.0069(7) 0.0061(6) 0.0062(6) C4 0.0186(7) 0.0237(9) 0.0225(9) 0.0087(8) 0.0064(7) 0.0051(7) C5 0.0185(7) 0.0248(9) 0.0217(9) 0.0075(8) 0.0060(7) 0.0052(7) C6 0.0192(8) 0.0251(9) 0.0243(9) 0.0098(8) 0.0068(7) 0.0061(7) C7 0.0199(7) 0.0248(9) 0.0243(9) 0.0089(8) 0.0056(7) 0.0051(7) C8 0.0201(8) 0.0322(10) 0.0292(10) 0.0134(9) 0.0066(7) 0.0059(7) C9 0.0218(8) 0.0403(12) 0.0331(11) 0.0124(10) 0.0030(8) 0.0052(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 Br1 C1 1.9006(18) . ? C1 C2 1.394(2) . ? C1 C3 1.397(2) 2_556 ? C2 C3 1.392(3) . ? C2 H2 0.9500 . ? C3 C1 1.397(2) 2_556 ? C3 C4 1.519(2) . ? C4 C5 1.525(2) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.530(2) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.527(2) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.524(2) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.525(3) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 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 C2 C1 C3 122.93(16) . 2_556 ? C2 C1 Br1 117.22(13) . . ? C3 C1 Br1 119.83(13) 2_556 . ? C3 C2 C1 120.95(16) . . ? C3 C2 H2 119.5 . . ? C1 C2 H2 119.5 . . ? C2 C3 C1 116.11(15) . 2_556 ? C2 C3 C4 122.48(16) . . ? C1 C3 C4 121.40(16) 2_556 . ? C3 C4 C5 115.74(15) . . ? C3 C4 H4A 108.3 . . ? C5 C4 H4A 108.3 . . ? C3 C4 H4B 108.3 . . ? C5 C4 H4B 108.3 . . ? H4A C4 H4B 107.4 . . ? C4 C5 C6 112.12(15) . . ? C4 C5 H5A 109.2 . . ? C6 C5 H5A 109.2 . . ? C4 C5 H5B 109.2 . . ? C6 C5 H5B 109.2 . . ? H5A C5 H5B 107.9 . . ? C7 C6 C5 111.59(16) . . ? C7 C6 H6A 109.3 . . ? C5 C6 H6A 109.3 . . ? C7 C6 H6B 109.3 . . ? C5 C6 H6B 109.3 . . ? H6A C6 H6B 108.0 . . ? C8 C7 C6 113.66(16) . . ? C8 C7 H7A 108.8 . . ? C6 C7 H7A 108.8 . . ? C8 C7 H7B 108.8 . . ? C6 C7 H7B 108.8 . . ? H7A C7 H7B 107.7 . . ? C7 C8 C9 111.73(17) . . ? C7 C8 H8A 109.3 . . ? C9 C8 H8A 109.3 . . ? C7 C8 H8B 109.3 . . ? C9 C8 H8B 109.3 . . ? H8A C8 H8B 107.9 . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 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 C3 C1 C2 C3 -0.9(3) 2_556 . . . ? Br1 C1 C2 C3 -179.60(13) . . . . ? C1 C2 C3 C1 0.8(3) . . . 2_556 ? C1 C2 C3 C4 179.94(15) . . . . ? C2 C3 C4 C5 0.1(2) . . . . ? C1 C3 C4 C5 179.16(15) 2_556 . . . ? C3 C4 C5 C6 179.14(14) . . . . ? C4 C5 C6 C7 -177.78(14) . . . . ? C5 C6 C7 C8 -178.56(15) . . . . ? C6 C7 C8 C9 -175.95(17) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.383 _refine_diff_density_min -0.545 _refine_diff_density_rms 0.089 data_wa956 _database_code_depnum_ccdc_archive 'CCDC 793268' #TrackingRef 'publ.cif' # start Validation Reply Form _vrf_PLAT241_wa956 ; PROBLEM: Check High Ueq as Compared to Neighbors for C6 RESPONSE: The hexyl chain is disordered. ; _vrf_PLAT242_wa956 ; PROBLEM: Check Low Ueq as Compared to Neighbors for C7' RESPONSE: The hexyl chain is disordered. ; # end Validation Reply Form _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C30 H52 B2 O4' _chemical_formula_sum 'C30 H52 B2 O4' _chemical_formula_weight 498.34 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' O O 0.0106 0.0060 '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 7.6693(9) _cell_length_b 9.4074(10) _cell_length_c 11.9721(13) _cell_angle_alpha 76.715(8) _cell_angle_beta 86.255(9) _cell_angle_gamma 73.941(8) _cell_volume 807.84(16) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 10863 _cell_measurement_theta_min 3.3 _cell_measurement_theta_max 25.9 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.51 _exptl_crystal_size_mid 0.48 _exptl_crystal_size_min 0.39 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.024 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 274 _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 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type '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 13355 _diffrn_reflns_av_R_equivalents 0.0754 _diffrn_reflns_av_sigmaI/netI 0.0451 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.27 _diffrn_reflns_theta_max 25.03 _reflns_number_total 2851 _reflns_number_gt 2141 _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^)+(0.1331P)^2^+0.2348P] 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 0.12(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2851 _refine_ls_number_parameters 163 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1003 _refine_ls_R_factor_gt 0.0841 _refine_ls_wR_factor_ref 0.2677 _refine_ls_wR_factor_gt 0.2535 _refine_ls_goodness_of_fit_ref 1.112 _refine_ls_restrained_S_all 1.112 _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 0.9548(3) 0.6519(3) 0.4352(2) 0.0632(7) Uani 1 1 d . . . B1 B 0.8946(4) 0.8245(3) 0.3738(3) 0.0647(8) Uani 1 1 d . . . O1 O 0.7853(3) 0.92796(19) 0.42885(16) 0.0784(7) Uani 1 1 d . . . O2 O 0.9389(3) 0.8874(2) 0.26657(17) 0.0833(7) Uani 1 1 d . . . C2 C 0.8722(4) 0.6085(3) 0.5398(2) 0.0688(8) Uani 1 1 d . . . H2 H 0.7846 0.6829 0.5671 0.083 Uiso 1 1 calc R . . C3 C 0.9120(4) 0.4619(3) 0.6058(2) 0.0692(8) Uani 1 1 d . . . C4 C 0.8084(5) 0.4288(4) 0.7152(3) 0.0921(11) Uani 1 1 d . . . H4A H 0.8886 0.3508 0.7710 0.111 Uiso 1 1 calc R . . H4B H 0.7700 0.5196 0.7458 0.111 Uiso 1 1 calc R . . C5 C 0.6463(6) 0.3777(5) 0.7002(4) 0.1187(15) Uani 1 1 d . A . H5A H 0.6836 0.2810 0.6777 0.142 Uiso 1 1 calc R . . H5B H 0.5690 0.4509 0.6404 0.142 Uiso 1 1 calc R . . C6 C 0.5403(9) 0.3615(9) 0.8160(6) 0.186(3) Uani 1 1 d . . . H6A H 0.6065 0.3905 0.8695 0.223 Uiso 0.308(13) 1 calc PR A 1 H6B H 0.4249 0.4382 0.8027 0.223 Uiso 0.308(13) 1 calc PR A 1 H6C H 0.6161 0.2821 0.8731 0.223 Uiso 0.692(13) 1 calc PR A 2 H6D H 0.5170 0.4556 0.8418 0.223 Uiso 0.692(13) 1 calc PR A 2 C7 C 0.508(3) 0.252(2) 0.8635(16) 0.135(7) Uiso 0.308(13) 1 d P A 1 H7A H 0.6160 0.1926 0.9078 0.162 Uiso 0.308(13) 1 calc PR A 1 H7B H 0.4995 0.1983 0.8049 0.162 Uiso 0.308(13) 1 calc PR A 1 C7' C 0.3777(13) 0.3282(11) 0.8098(7) 0.147(4) Uiso 0.692(13) 1 d P A 2 H7'1 H 0.4029 0.2368 0.7803 0.176 Uiso 0.692(13) 1 calc PR A 2 H7'2 H 0.3032 0.4095 0.7532 0.176 Uiso 0.692(13) 1 calc PR A 2 C8 C 0.3377(19) 0.2386(16) 0.9495(12) 0.093(4) Uiso 0.308(13) 1 d P A 1 H8A H 0.2453 0.2183 0.9086 0.112 Uiso 0.308(13) 1 calc PR A 1 H8B H 0.3782 0.1525 1.0131 0.112 Uiso 0.308(13) 1 calc PR A 1 C8' C 0.255(3) 0.303(2) 0.9271(14) 0.231(7) Uiso 0.692(13) 1 d P A 2 H8C H 0.1298 0.3245 0.9037 0.277 Uiso 0.692(13) 1 calc PR A 2 H8D H 0.2932 0.1965 0.9645 0.277 Uiso 0.692(13) 1 calc PR A 2 C9 C 0.2566(14) 0.3719(13) 0.9949(8) 0.249(5) Uani 1 1 d . . . H9A H 0.2759 0.4598 0.9420 0.373 Uiso 0.308(13) 1 calc PR A 1 H9B H 0.3114 0.3611 1.0672 0.373 Uiso 0.308(13) 1 calc PR A 1 H9C H 0.1287 0.3832 1.0054 0.373 Uiso 0.308(13) 1 calc PR A 1 H9D H 0.3156 0.4501 0.9636 0.373 Uiso 0.692(13) 1 calc PR A 2 H9E H 0.3214 0.3059 1.0614 0.373 Uiso 0.692(13) 1 calc PR A 2 H9F H 0.1344 0.4170 1.0160 0.373 Uiso 0.692(13) 1 calc PR A 2 C10 C 0.7299(4) 1.0720(3) 0.3463(3) 0.0743(8) Uani 1 1 d . . . C11 C 0.8793(4) 1.0529(3) 0.2532(3) 0.0784(8) Uani 1 1 d . . . C12 C 0.5420(4) 1.0854(4) 0.3064(4) 0.1016(11) Uani 1 1 d . . . H12A H 0.4576 1.0972 0.3687 0.152 Uiso 1 1 calc R . . H12B H 0.5422 0.9955 0.2814 0.152 Uiso 1 1 calc R . . H12C H 0.5067 1.1720 0.2439 0.152 Uiso 1 1 calc R . . C13 C 0.7207(6) 1.1980(4) 0.4083(3) 0.1090(13) Uani 1 1 d . . . H13A H 0.8403 1.1911 0.4325 0.163 Uiso 1 1 calc R . . H13B H 0.6431 1.1878 0.4742 0.163 Uiso 1 1 calc R . . H13C H 0.6731 1.2946 0.3574 0.163 Uiso 1 1 calc R . . C14 C 0.8153(6) 1.1222(4) 0.1304(3) 0.1094(13) Uani 1 1 d . . . H14A H 0.9166 1.1049 0.0791 0.164 Uiso 1 1 calc R . . H14B H 0.7625 1.2294 0.1217 0.164 Uiso 1 1 calc R . . H14C H 0.7262 1.0763 0.1128 0.164 Uiso 1 1 calc R . . C15 C 1.0451(5) 1.1017(5) 0.2760(4) 0.1142(13) Uani 1 1 d . . . H15A H 1.1321 1.0868 0.2155 0.171 Uiso 1 1 calc R . . H15B H 1.0986 1.0421 0.3480 0.171 Uiso 1 1 calc R . . H15C H 1.0089 1.2070 0.2789 0.171 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 0.0631(14) 0.0501(13) 0.0705(15) -0.0144(11) 0.0031(12) -0.0055(11) B1 0.0607(16) 0.0565(16) 0.0709(18) -0.0121(13) -0.0006(13) -0.0073(12) O1 0.0894(13) 0.0504(10) 0.0793(12) -0.0075(8) 0.0058(10) 0.0003(9) O2 0.0904(14) 0.0597(11) 0.0813(13) -0.0040(9) 0.0122(10) -0.0025(9) C2 0.0703(16) 0.0529(14) 0.0743(16) -0.0176(12) 0.0097(13) -0.0016(11) C3 0.0718(16) 0.0563(15) 0.0719(16) -0.0153(12) 0.0102(13) -0.0061(12) C4 0.109(2) 0.0686(18) 0.0776(19) -0.0119(14) 0.0310(17) -0.0002(16) C5 0.102(3) 0.099(3) 0.126(3) 0.001(2) 0.044(2) -0.011(2) C6 0.165(5) 0.189(6) 0.201(6) -0.020(5) 0.077(5) -0.078(5) C9 0.295(11) 0.288(12) 0.212(8) -0.089(8) 0.080(8) -0.147(10) C10 0.0814(18) 0.0490(14) 0.0822(18) -0.0079(12) -0.0089(14) -0.0043(12) C11 0.0816(18) 0.0564(15) 0.0853(19) -0.0016(13) -0.0065(15) -0.0092(13) C12 0.075(2) 0.092(2) 0.126(3) -0.023(2) -0.0096(19) -0.0017(17) C13 0.146(3) 0.0601(18) 0.112(3) -0.0213(17) -0.016(2) -0.0079(19) C14 0.131(3) 0.088(2) 0.085(2) 0.0063(18) -0.012(2) -0.009(2) C15 0.100(3) 0.104(3) 0.135(3) 0.002(2) -0.008(2) -0.044(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 1.393(4) . ? C1 C3 1.415(3) 2_766 ? C1 B1 1.571(4) . ? B1 O2 1.349(4) . ? B1 O1 1.362(3) . ? O1 C10 1.455(3) . ? O2 C11 1.469(3) . ? C2 C3 1.385(4) . ? C2 H2 0.9300 . ? C3 C1 1.415(3) 2_766 ? C3 C4 1.502(4) . ? C4 C5 1.486(6) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C6 1.560(6) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C7 1.139(18) . ? C6 C7' 1.377(10) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C6 H6C 0.9700 . ? C6 H6D 0.9700 . ? C7 C8 1.63(2) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C7' C8' 1.647(16) . ? C7' H7'1 0.9700 . ? C7' H7'2 0.9700 . ? C8 C9 1.446(17) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C8' C9 1.151(15) . ? C8' H8C 0.9700 . ? C8' H8D 0.9700 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C9 H9D 0.9600 . ? C9 H9E 0.9600 . ? C9 H9F 0.9600 . ? C10 C12 1.510(4) . ? C10 C13 1.521(4) . ? C10 C11 1.549(4) . ? C11 C14 1.519(4) . ? C11 C15 1.526(5) . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C3 117.5(2) . 2_766 ? C2 C1 B1 117.0(2) . . ? C3 C1 B1 125.4(2) 2_766 . ? O2 B1 O1 112.8(2) . . ? O2 B1 C1 126.8(2) . . ? O1 B1 C1 120.4(2) . . ? B1 O1 C10 108.1(2) . . ? B1 O2 C11 107.5(2) . . ? C3 C2 C1 124.3(2) . . ? C3 C2 H2 117.8 . . ? C1 C2 H2 117.8 . . ? C2 C3 C1 118.1(2) . 2_766 ? C2 C3 C4 119.1(2) . . ? C1 C3 C4 122.7(2) 2_766 . ? C5 C4 C3 113.4(3) . . ? C5 C4 H4A 108.9 . . ? C3 C4 H4A 108.9 . . ? C5 C4 H4B 108.9 . . ? C3 C4 H4B 108.9 . . ? H4A C4 H4B 107.7 . . ? C4 C5 C6 108.7(4) . . ? C4 C5 H5A 109.9 . . ? C6 C5 H5A 109.9 . . ? C4 C5 H5B 109.9 . . ? C6 C5 H5B 109.9 . . ? H5A C5 H5B 108.3 . . ? C7 C6 C7' 55.2(10) . . ? C7 C6 C5 123.7(11) . . ? C7' C6 C5 114.0(7) . . ? C7 C6 H6A 106.4 . . ? C7' C6 H6A 139.1 . . ? C5 C6 H6A 106.4 . . ? C7 C6 H6B 106.4 . . ? C7' C6 H6B 56.7 . . ? C5 C6 H6B 106.4 . . ? H6A C6 H6B 106.5 . . ? C7 C6 H6C 53.8 . . ? C7' C6 H6C 108.7 . . ? C5 C6 H6C 108.7 . . ? H6A C6 H6C 61.6 . . ? H6B C6 H6C 144.8 . . ? C7 C6 H6D 127.4 . . ? C7' C6 H6D 108.7 . . ? C5 C6 H6D 108.7 . . ? H6A C6 H6D 49.5 . . ? H6B C6 H6D 58.1 . . ? H6C C6 H6D 107.6 . . ? C6 C7 C8 126.1(15) . . ? C6 C7 H7A 105.8 . . ? C8 C7 H7A 105.8 . . ? C6 C7 H7B 105.8 . . ? C8 C7 H7B 105.8 . . ? H7A C7 H7B 106.2 . . ? C6 C7' C8' 119.0(8) . . ? C6 C7' H7'1 107.6 . . ? C8' C7' H7'1 107.6 . . ? C6 C7' H7'2 107.6 . . ? C8' C7' H7'2 107.6 . . ? H7'1 C7' H7'2 107.0 . . ? C9 C8 C7 114.5(11) . . ? C9 C8 H8A 108.6 . . ? C7 C8 H8A 108.6 . . ? C9 C8 H8B 108.6 . . ? C7 C8 H8B 108.6 . . ? H8A C8 H8B 107.6 . . ? C9 C8' C7' 119.0(14) . . ? C9 C8' H8C 107.6 . . ? C7' C8' H8C 107.6 . . ? C9 C8' H8D 107.6 . . ? C7' C8' H8D 107.6 . . ? H8C C8' H8D 107.0 . . ? C8 C9 H9A 109.5 . . ? C8' C9 H9B 140.4 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C8' C9 H9D 109.5 . . ? C8' C9 H9E 109.5 . . ? H9D C9 H9E 109.5 . . ? C8' C9 H9F 109.5 . . ? H9D C9 H9F 109.5 . . ? H9E C9 H9F 109.5 . . ? O1 C10 C12 106.7(3) . . ? O1 C10 C13 107.9(2) . . ? C12 C10 C13 109.2(3) . . ? O1 C10 C11 102.1(2) . . ? C12 C10 C11 114.6(3) . . ? C13 C10 C11 115.5(3) . . ? O2 C11 C14 107.7(3) . . ? O2 C11 C15 106.6(3) . . ? C14 C11 C15 110.3(3) . . ? O2 C11 C10 102.2(2) . . ? C14 C11 C10 115.4(3) . . ? C15 C11 C10 113.8(3) . . ? C10 C12 H12A 109.5 . . ? C10 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C10 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C10 C13 H13A 109.5 . . ? C10 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C10 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C11 C14 H14A 109.5 . . ? C11 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C11 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C11 C15 H15A 109.5 . . ? C11 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C11 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 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 C2 C1 B1 O2 -170.9(3) . . . . ? C3 C1 B1 O2 10.3(5) 2_766 . . . ? C2 C1 B1 O1 8.7(4) . . . . ? C3 C1 B1 O1 -170.1(3) 2_766 . . . ? O2 B1 O1 C10 8.3(3) . . . . ? C1 B1 O1 C10 -171.3(2) . . . . ? O1 B1 O2 C11 10.1(3) . . . . ? C1 B1 O2 C11 -170.3(3) . . . . ? C3 C1 C2 C3 0.0(5) 2_766 . . . ? B1 C1 C2 C3 -178.8(3) . . . . ? C1 C2 C3 C1 0.0(5) . . . 2_766 ? C1 C2 C3 C4 -177.9(3) . . . . ? C2 C3 C4 C5 92.8(4) . . . . ? C1 C3 C4 C5 -85.0(4) 2_766 . . . ? C3 C4 C5 C6 -174.8(4) . . . . ? C4 C5 C6 C7 -122.7(14) . . . . ? C4 C5 C6 C7' 174.3(6) . . . . ? C7' C6 C7 C8 -55.2(16) . . . . ? C5 C6 C7 C8 -152.8(12) . . . . ? C7 C6 C7' C8' 62.7(15) . . . . ? C5 C6 C7' C8' 178.2(9) . . . . ? C6 C7 C8 C9 -20(2) . . . . ? C6 C7' C8' C9 33(2) . . . . ? C7' C8' C9 C8 -87(2) . . . . ? C7 C8 C9 C8' 96(2) . . . . ? B1 O1 C10 C12 98.9(3) . . . . ? B1 O1 C10 C13 -143.8(3) . . . . ? B1 O1 C10 C11 -21.6(3) . . . . ? B1 O2 C11 C14 -144.6(3) . . . . ? B1 O2 C11 C15 97.0(3) . . . . ? B1 O2 C11 C10 -22.6(3) . . . . ? O1 C10 C11 O2 26.2(3) . . . . ? C12 C10 C11 O2 -88.6(3) . . . . ? C13 C10 C11 O2 143.1(3) . . . . ? O1 C10 C11 C14 142.8(3) . . . . ? C12 C10 C11 C14 28.0(4) . . . . ? C13 C10 C11 C14 -100.3(3) . . . . ? O1 C10 C11 C15 -88.2(3) . . . . ? C12 C10 C11 C15 156.9(3) . . . . ? C13 C10 C11 C15 28.6(4) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.368 _refine_diff_density_min -0.284 _refine_diff_density_rms 0.041 data_wa920 _database_code_depnum_ccdc_archive 'CCDC 793269' #TrackingRef 'publ.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C34 H66 B2 Li2 O4' _chemical_formula_sum 'C34 H66 B2 Li2 O4' _chemical_formula_weight 574.37 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 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 9.2666(10) _cell_length_b 14.2673(15) _cell_length_c 15.9830(19) _cell_angle_alpha 67.763(8) _cell_angle_beta 76.707(9) _cell_angle_gamma 75.464(9) _cell_volume 1871.7(4) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 4459 _cell_measurement_theta_min 3.3 _cell_measurement_theta_max 26.0 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.019 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 636 _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 11646 _diffrn_reflns_av_R_equivalents 0.0788 _diffrn_reflns_av_sigmaI/netI 0.1397 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.39 _diffrn_reflns_theta_max 25.03 _reflns_number_total 6579 _reflns_number_gt 3327 _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^)+(0.0464P)^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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6579 _refine_ls_number_parameters 381 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1275 _refine_ls_R_factor_gt 0.0572 _refine_ls_wR_factor_ref 0.1117 _refine_ls_wR_factor_gt 0.0961 _refine_ls_goodness_of_fit_ref 0.829 _refine_ls_restrained_S_all 0.829 _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 0.3752(4) 0.31109(18) 0.21234(17) 0.0283(9) Uani 1 1 d . . . Li2 Li 0.1484(4) 0.16145(18) 0.26053(17) 0.0271(9) Uani 1 1 d . . . B1 B 0.3245(3) 0.16978(12) 0.35512(12) 0.0261(6) Uani 1 1 d . . . H1A H 0.2165 0.1679 0.3740 0.039 Uiso 1 1 calc R . . H1B H 0.3580 0.1575 0.2968 0.039 Uiso 1 1 calc R . . H1C H 0.3424 0.2374 0.3479 0.039 Uiso 1 1 calc R . . C1 C 0.4175(2) 0.08166(11) 0.43196(10) 0.0194(5) Uani 1 1 d . . . C2 C 0.5331(2) 0.00528(12) 0.41113(10) 0.0210(5) Uani 1 1 d . . . H2 H 0.5581 0.0080 0.3493 0.025 Uiso 1 1 calc R . . C3 C 0.6134(2) -0.07415(11) 0.47523(11) 0.0203(5) Uani 1 1 d . . . C4 C 0.7265(2) -0.15644(11) 0.44370(10) 0.0248(5) Uani 1 1 d . . . H4A H 0.8057 -0.1873 0.4836 0.030 Uiso 1 1 calc R . . H4B H 0.7756 -0.1245 0.3805 0.030 Uiso 1 1 calc R . . C5 C 0.6488(2) -0.24053(12) 0.44686(11) 0.0297(5) Uani 1 1 d . . . H5A H 0.5941 -0.2682 0.5094 0.036 Uiso 1 1 calc R . . H5B H 0.5730 -0.2090 0.4047 0.036 Uiso 1 1 calc R . . C6 C 0.7540(2) -0.32973(11) 0.42154(11) 0.0313(6) Uani 1 1 d . . . H6A H 0.8220 -0.3672 0.4680 0.038 Uiso 1 1 calc R . . H6B H 0.8170 -0.3021 0.3619 0.038 Uiso 1 1 calc R . . C7 C 0.6685(3) -0.40491(13) 0.41532(13) 0.0410(6) Uani 1 1 d . . . H7A H 0.6071 -0.4329 0.4755 0.049 Uiso 1 1 calc R . . H7B H 0.5981 -0.3662 0.3704 0.049 Uiso 1 1 calc R . . C8 C 0.7666(3) -0.49497(14) 0.38780(13) 0.0481(7) Uani 1 1 d . . . H8A H 0.7015 -0.5300 0.3728 0.058 Uiso 1 1 calc R . . H8B H 0.8381 -0.4680 0.3319 0.058 Uiso 1 1 calc R . . C9 C 0.8549(4) -0.57287(15) 0.46167(15) 0.0609(9) Uani 1 1 d . . . H9A H 0.9153 -0.6287 0.4402 0.091 Uiso 1 1 calc R . . H9B H 0.7849 -0.6011 0.5168 0.091 Uiso 1 1 calc R . . H9C H 0.9217 -0.5392 0.4758 0.091 Uiso 1 1 calc R . . B1A B 0.1879(3) 0.31041(13) 0.12300(12) 0.0285(6) Uani 1 1 d . . . H1A1 H 0.1649 0.2473 0.1224 0.043 Uiso 1 1 calc R . . H1A2 H 0.1624 0.3123 0.1854 0.043 Uiso 1 1 calc R . . H1A3 H 0.2956 0.3116 0.1016 0.043 Uiso 1 1 calc R . . C1A C 0.0901(2) 0.40951(12) 0.05626(11) 0.0237(5) Uani 1 1 d . . . C2A C -0.0271(3) 0.47368(12) 0.09223(10) 0.0232(5) Uani 1 1 d . . . H2A H -0.0480 0.4563 0.1568 0.028 Uiso 1 1 calc R . . C3A C -0.1156(2) 0.56177(12) 0.03936(11) 0.0229(5) Uani 1 1 d . . . C4A C -0.2335(2) 0.62672(11) 0.08770(10) 0.0272(6) Uani 1 1 d . . . H4A1 H -0.2684 0.5817 0.1500 0.033 Uiso 1 1 calc R . . H4A2 H -0.3213 0.6558 0.0544 0.033 Uiso 1 1 calc R . . C5A C -0.1775(3) 0.71517(12) 0.09518(11) 0.0319(6) Uani 1 1 d . . . H5A1 H -0.0901 0.6863 0.1289 0.038 Uiso 1 1 calc R . . H5A2 H -0.1424 0.7603 0.0330 0.038 Uiso 1 1 calc R . . C6A C -0.2972(3) 0.77944(13) 0.14338(12) 0.0418(7) Uani 1 1 d . . . H6A1 H -0.3413 0.7329 0.2023 0.050 Uiso 1 1 calc R . . H6A2 H -0.3789 0.8149 0.1056 0.050 Uiso 1 1 calc R . . C7A C -0.2396(3) 0.86056(15) 0.16225(14) 0.0534(8) Uani 1 1 d . . . H7A1 H -0.3229 0.8938 0.1988 0.064 Uiso 1 1 calc R . . H7A2 H -0.1581 0.8247 0.2002 0.064 Uiso 1 1 calc R . . C8A C -0.1808(4) 0.94309(16) 0.07967(15) 0.0583(9) Uani 1 1 d . . . H8A1 H -0.0994 0.9105 0.0417 0.070 Uiso 1 1 calc R . . H8A2 H -0.1364 0.9860 0.0996 0.070 Uiso 1 1 calc R . . C9A C -0.3015(4) 1.01211(18) 0.02162(17) 0.0803(12) Uani 1 1 d . . . H9A1 H -0.2570 1.0653 -0.0305 0.120 Uiso 1 1 calc R . . H9A2 H -0.3824 1.0448 0.0587 0.120 Uiso 1 1 calc R . . H9A3 H -0.3428 0.9707 -0.0007 0.120 Uiso 1 1 calc R . . O11 O 0.33800(18) 0.45097(8) 0.21962(8) 0.0357(4) Uani 1 1 d . . . C12 C 0.1904(3) 0.49579(14) 0.25026(15) 0.0492(7) Uani 1 1 d . . . H12A H 0.1469 0.4469 0.3078 0.059 Uiso 1 1 calc R . . H12B H 0.1241 0.5145 0.2037 0.059 Uiso 1 1 calc R . . C13 C 0.2053(4) 0.5908(2) 0.2657(2) 0.0692(9) Uani 1 1 d . . . H13A H 0.1752 0.6538 0.2143 0.083 Uiso 1 1 calc R . . H13B H 0.1420 0.5965 0.3232 0.083 Uiso 1 1 calc R . . C14 C 0.3685(4) 0.5756(2) 0.2712(2) 0.0804(10) Uani 1 1 d . . . H14A H 0.4146 0.6321 0.2227 0.097 Uiso 1 1 calc R . . H14B H 0.3817 0.5742 0.3314 0.097 Uiso 1 1 calc R . . C15 C 0.4372(4) 0.4785(2) 0.2588(3) 0.0851(11) Uani 1 1 d . . . H15A H 0.5351 0.4844 0.2179 0.102 Uiso 1 1 calc R . . H15B H 0.4558 0.4249 0.3184 0.102 Uiso 1 1 calc R . . O21 O 0.58832(18) 0.29983(8) 0.15893(8) 0.0332(4) Uani 1 1 d . . . C22 C 0.6277(3) 0.37958(15) 0.07391(15) 0.0616(10) Uani 1 1 d . . . H22A H 0.6709 0.4297 0.0853 0.074 Uiso 1 1 calc R . . H22B H 0.5370 0.4167 0.0443 0.074 Uiso 1 1 calc R . . C23 C 0.7401(4) 0.32930(18) 0.01428(15) 0.0668(10) Uani 1 1 d . . . H23A H 0.8155 0.3730 -0.0231 0.080 Uiso 1 1 calc R . . H23B H 0.6907 0.3142 -0.0268 0.080 Uiso 1 1 calc R . . C24 C 0.8122(3) 0.23092(16) 0.08182(16) 0.0555(8) Uani 1 1 d . . . H24A H 0.8542 0.1767 0.0539 0.067 Uiso 1 1 calc R . . H24B H 0.8930 0.2430 0.1056 0.067 Uiso 1 1 calc R . . C25 C 0.6804(3) 0.20296(13) 0.15591(13) 0.0402(7) Uani 1 1 d . . . H25A H 0.6229 0.1629 0.1411 0.048 Uiso 1 1 calc R . . H25B H 0.7154 0.1616 0.2155 0.048 Uiso 1 1 calc R . . O31 O -0.06568(18) 0.16891(8) 0.31154(8) 0.0308(4) Uani 1 1 d . . . C32 C -0.1008(3) 0.08932(14) 0.39747(13) 0.0521(8) Uani 1 1 d . . . H32A H -0.0075 0.0498 0.4234 0.063 Uiso 1 1 calc R . . H32B H -0.1519 0.0412 0.3888 0.063 Uiso 1 1 calc R . . C33 C -0.2031(3) 0.14245(15) 0.46026(13) 0.0567(9) Uani 1 1 d . . . H33A H -0.1447 0.1607 0.4947 0.068 Uiso 1 1 calc R . . H33B H -0.2749 0.0990 0.5039 0.068 Uiso 1 1 calc R . . C34 C -0.2833(3) 0.23720(15) 0.39429(15) 0.0476(7) Uani 1 1 d . . . H34A H -0.3224 0.2929 0.4207 0.057 Uiso 1 1 calc R . . H34B H -0.3677 0.2217 0.3764 0.057 Uiso 1 1 calc R . . C35 C -0.1597(3) 0.26589(13) 0.31393(13) 0.0379(6) Uani 1 1 d . . . H35A H -0.2027 0.3036 0.2564 0.045 Uiso 1 1 calc R . . H35B H -0.1008 0.3097 0.3227 0.045 Uiso 1 1 calc R . . O41 O 0.18270(19) 0.02077(9) 0.25874(9) 0.0389(4) Uani 1 1 d . . . C42 C 0.0864(3) -0.01500(17) 0.22382(17) 0.0544(7) Uani 1 1 d . . . H42A H 0.1022 0.0120 0.1561 0.065 Uiso 1 1 calc R . . H42B H -0.0209 0.0068 0.2464 0.065 Uiso 1 1 calc R . . C43 C 0.1302(4) -0.12921(19) 0.2584(2) 0.0797(11) Uani 1 1 d . . . H43A H 0.0647 -0.1593 0.3163 0.096 Uiso 1 1 calc R . . H43B H 0.1217 -0.1585 0.2130 0.096 Uiso 1 1 calc R . . C44 C 0.2890(4) -0.15062(19) 0.2737(2) 0.0736(10) Uani 1 1 d . . . H44A H 0.3575 -0.1786 0.2278 0.088 Uiso 1 1 calc R . . H44B H 0.3016 -0.2010 0.3355 0.088 Uiso 1 1 calc R . . C45 C 0.3216(3) -0.04997(15) 0.26406(16) 0.0503(7) Uani 1 1 d . . . H45A H 0.3654 -0.0565 0.3174 0.060 Uiso 1 1 calc R . . H45B H 0.3944 -0.0260 0.2080 0.060 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 0.031(2) 0.0236(13) 0.0308(14) -0.0061(10) -0.0075(14) -0.0086(14) Li2 0.025(2) 0.0220(13) 0.0306(14) -0.0023(10) -0.0069(14) -0.0054(13) B1 0.0278(15) 0.0244(9) 0.0247(9) -0.0047(7) -0.0084(10) -0.0043(10) C1 0.0183(12) 0.0174(8) 0.0219(8) -0.0010(6) -0.0065(8) -0.0080(8) C2 0.0258(13) 0.0237(8) 0.0150(8) -0.0040(5) -0.0039(8) -0.0102(8) C3 0.0189(12) 0.0169(8) 0.0244(9) -0.0040(6) -0.0058(8) -0.0042(8) C4 0.0228(13) 0.0248(8) 0.0249(9) -0.0080(6) -0.0050(8) -0.0004(8) C5 0.0269(13) 0.0260(8) 0.0367(10) -0.0112(6) -0.0055(9) -0.0042(9) C6 0.0277(14) 0.0298(9) 0.0389(10) -0.0151(6) -0.0080(9) -0.0013(9) C7 0.0408(16) 0.0318(10) 0.0595(13) -0.0230(7) -0.0163(11) -0.0030(10) C8 0.059(2) 0.0369(11) 0.0616(14) -0.0276(7) -0.0247(13) -0.0014(12) C9 0.081(2) 0.0361(11) 0.0767(16) -0.0254(8) -0.0401(16) 0.0056(13) B1A 0.0294(15) 0.0295(9) 0.0250(9) -0.0028(7) -0.0108(10) -0.0063(10) C1A 0.0249(13) 0.0223(9) 0.0256(9) -0.0029(6) -0.0098(9) -0.0103(9) C2A 0.0257(13) 0.0260(9) 0.0182(8) -0.0012(6) -0.0070(9) -0.0116(9) C3A 0.0220(13) 0.0210(9) 0.0265(9) -0.0041(6) -0.0091(9) -0.0069(9) C4A 0.0225(13) 0.0283(8) 0.0258(9) -0.0017(6) -0.0046(8) -0.0072(8) C5A 0.0303(14) 0.0358(9) 0.0306(9) -0.0085(6) -0.0037(9) -0.0128(9) C6A 0.0441(17) 0.0387(10) 0.0441(11) -0.0176(7) -0.0018(11) -0.0090(11) C7A 0.060(2) 0.0512(13) 0.0575(14) -0.0287(9) -0.0080(14) -0.0089(14) C8A 0.065(2) 0.0525(13) 0.0684(15) -0.0325(9) -0.0025(15) -0.0186(14) C9A 0.111(3) 0.0615(14) 0.0705(15) -0.0168(11) -0.0284(18) -0.0142(18) O11 0.0316(10) 0.0249(6) 0.0518(8) -0.0139(5) -0.0081(7) -0.0041(6) C12 0.0335(17) 0.0457(12) 0.0733(15) -0.0290(8) -0.0068(13) -0.0029(11) C13 0.053(2) 0.0741(18) 0.106(2) -0.0664(12) -0.0167(19) 0.0044(17) C14 0.059(2) 0.092(2) 0.128(3) -0.0786(16) -0.022(2) -0.007(2) C15 0.045(2) 0.065(2) 0.178(4) -0.0688(16) -0.039(2) -0.0041(17) O21 0.0256(10) 0.0257(7) 0.0423(8) -0.0058(5) -0.0045(7) -0.0038(6) C22 0.0409(18) 0.0412(12) 0.0763(16) 0.0090(11) 0.0021(14) -0.0173(12) C23 0.067(2) 0.0833(17) 0.0418(13) -0.0073(11) 0.0030(15) -0.0321(17) C24 0.0436(19) 0.0480(12) 0.0729(15) -0.0285(9) 0.0115(14) -0.0107(13) C25 0.0349(16) 0.0303(11) 0.0520(12) -0.0128(7) -0.0051(11) -0.0035(10) O31 0.0274(9) 0.0261(7) 0.0348(7) -0.0053(4) -0.0047(7) -0.0058(6) C32 0.0509(19) 0.0352(10) 0.0545(13) -0.0021(9) 0.0112(13) -0.0186(11) C33 0.066(2) 0.0551(12) 0.0454(12) -0.0133(9) 0.0174(13) -0.0343(14) C34 0.0321(17) 0.0454(12) 0.0712(14) -0.0321(8) 0.0108(13) -0.0150(12) C35 0.0320(15) 0.0310(10) 0.0504(12) -0.0166(7) -0.0062(11) -0.0012(10) O41 0.0357(11) 0.0284(7) 0.0594(9) -0.0200(5) -0.0202(8) 0.0019(7) C42 0.0416(19) 0.0581(15) 0.0836(19) -0.0437(9) -0.0311(15) 0.0067(13) C43 0.057(2) 0.0439(15) 0.154(3) -0.0500(13) -0.019(2) -0.0081(15) C44 0.063(2) 0.0448(15) 0.132(3) -0.0489(11) -0.037(2) 0.0070(15) C45 0.0334(17) 0.0472(12) 0.0780(16) -0.0315(9) -0.0181(14) 0.0041(12) _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 O21 1.956(4) . ? Li1 O11 1.982(3) . ? Li1 Li2 3.135(4) . ? Li2 O31 1.956(4) . ? Li2 O41 1.962(3) . ? B1 C1 1.615(2) . ? B1 H1A 0.9800 . ? B1 H1B 0.9800 . ? B1 H1C 0.9800 . ? C1 C2 1.403(3) . ? C1 C3 1.412(3) 2_656 ? C2 C3 1.391(2) . ? C2 H2 0.9500 . ? C3 C1 1.412(3) 2_656 ? C3 C4 1.523(3) . ? C4 C5 1.527(2) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.523(3) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.527(3) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.526(4) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.514(3) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? B1A C1A 1.618(2) . ? B1A H1A1 0.9800 . ? B1A H1A2 0.9800 . ? B1A H1A3 0.9800 . ? C1A C2A 1.400(3) . ? C1A C3A 1.403(3) 2_565 ? C2A C3A 1.402(3) . ? C2A H2A 0.9500 . ? C3A C1A 1.403(3) 2_565 ? C3A C4A 1.515(3) . ? C4A C5A 1.532(3) . ? C4A H4A1 0.9900 . ? C4A H4A2 0.9900 . ? C5A C6A 1.515(3) . ? C5A H5A1 0.9900 . ? C5A H5A2 0.9900 . ? C6A C7A 1.538(3) . ? C6A H6A1 0.9900 . ? C6A H6A2 0.9900 . ? C7A C8A 1.4966(18) . ? C7A H7A1 0.9900 . ? C7A H7A2 0.9900 . ? C8A C9A 1.521(5) . ? C8A H8A1 0.9900 . ? C8A H8A2 0.9900 . ? C9A H9A1 0.9800 . ? C9A H9A2 0.9800 . ? C9A H9A3 0.9800 . ? O11 C12 1.417(3) . ? O11 C15 1.422(4) . ? C12 C13 1.510(4) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.491(5) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C15 1.440(4) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? O21 C25 1.442(3) . ? O21 C22 1.4438(12) . ? C22 C23 1.481(4) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C23 C24 1.515(3) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C24 C25 1.509(3) . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? C25 H25A 0.9900 . ? C25 H25B 0.9900 . ? O31 C32 1.4427(10) . ? O31 C35 1.447(3) . ? C32 C33 1.502(4) . ? C32 H32A 0.9900 . ? C32 H32B 0.9900 . ? C33 C34 1.506(3) . ? C33 H33A 0.9900 . ? C33 H33B 0.9900 . ? C34 C35 1.513(3) . ? C34 H34A 0.9900 . ? C34 H34B 0.9900 . ? C35 H35A 0.9900 . ? C35 H35B 0.9900 . ? O41 C45 1.420(3) . ? O41 C42 1.429(3) . ? C42 C43 1.488(3) . ? C42 H42A 0.9900 . ? C42 H42B 0.9900 . ? C43 C44 1.484(5) . ? C43 H43A 0.9900 . ? C43 H43B 0.9900 . ? C44 C45 1.486(3) . ? C44 H44A 0.9900 . ? C44 H44B 0.9900 . ? C45 H45A 0.9900 . ? C45 H45B 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 O21 Li1 O11 99.32(13) . . ? O21 Li1 Li2 131.14(17) . . ? O11 Li1 Li2 129.42(18) . . ? O31 Li2 O41 96.09(13) . . ? O31 Li2 Li1 133.26(17) . . ? O41 Li2 Li1 130.46(18) . . ? C1 B1 H1A 109.5 . . ? C1 B1 H1B 109.5 . . ? H1A B1 H1B 109.5 . . ? C1 B1 H1C 109.5 . . ? H1A B1 H1C 109.5 . . ? H1B B1 H1C 109.5 . . ? C2 C1 C3 115.25(14) . 2_656 ? C2 C1 B1 121.95(19) . . ? C3 C1 B1 122.8(2) 2_656 . ? C3 C2 C1 124.2(2) . . ? C3 C2 H2 117.9 . . ? C1 C2 H2 117.9 . . ? C2 C3 C1 120.5(2) . 2_656 ? C2 C3 C4 118.12(19) . . ? C1 C3 C4 121.20(14) 2_656 . ? C3 C4 C5 110.81(18) . . ? C3 C4 H4A 109.5 . . ? C5 C4 H4A 109.5 . . ? C3 C4 H4B 109.5 . . ? C5 C4 H4B 109.5 . . ? H4A C4 H4B 108.1 . . ? C6 C5 C4 114.89(18) . . ? C6 C5 H5A 108.5 . . ? C4 C5 H5A 108.5 . . ? C6 C5 H5B 108.5 . . ? C4 C5 H5B 108.5 . . ? H5A C5 H5B 107.5 . . ? C5 C6 C7 112.45(19) . . ? C5 C6 H6A 109.1 . . ? C7 C6 H6A 109.1 . . ? C5 C6 H6B 109.1 . . ? C7 C6 H6B 109.1 . . ? H6A C6 H6B 107.8 . . ? C8 C7 C6 115.4(2) . . ? C8 C7 H7A 108.4 . . ? C6 C7 H7A 108.4 . . ? C8 C7 H7B 108.4 . . ? C6 C7 H7B 108.4 . . ? H7A C7 H7B 107.5 . . ? C9 C8 C7 113.2(2) . . ? C9 C8 H8A 108.9 . . ? C7 C8 H8A 108.9 . . ? C9 C8 H8B 108.9 . . ? C7 C8 H8B 108.9 . . ? H8A C8 H8B 107.8 . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C1A B1A H1A1 109.5 . . ? C1A B1A H1A2 109.5 . . ? H1A1 B1A H1A2 109.5 . . ? C1A B1A H1A3 109.5 . . ? H1A1 B1A H1A3 109.5 . . ? H1A2 B1A H1A3 109.5 . . ? C2A C1A C3A 115.48(17) . 2_565 ? C2A C1A B1A 120.69(18) . . ? C3A C1A B1A 123.8(2) 2_565 . ? C1A C2A C3A 124.38(18) . . ? C1A C2A H2A 117.8 . . ? C3A C2A H2A 117.8 . . ? C2A C3A C1A 120.1(2) . 2_565 ? C2A C3A C4A 118.42(17) . . ? C1A C3A C4A 121.38(16) 2_565 . ? C3A C4A C5A 113.96(17) . . ? C3A C4A H4A1 108.8 . . ? C5A C4A H4A1 108.8 . . ? C3A C4A H4A2 108.8 . . ? C5A C4A H4A2 108.8 . . ? H4A1 C4A H4A2 107.7 . . ? C6A C5A C4A 113.13(17) . . ? C6A C5A H5A1 109.0 . . ? C4A C5A H5A1 109.0 . . ? C6A C5A H5A2 109.0 . . ? C4A C5A H5A2 109.0 . . ? H5A1 C5A H5A2 107.8 . . ? C5A C6A C7A 114.4(2) . . ? C5A C6A H6A1 108.7 . . ? C7A C6A H6A1 108.7 . . ? C5A C6A H6A2 108.7 . . ? C7A C6A H6A2 108.7 . . ? H6A1 C6A H6A2 107.6 . . ? C8A C7A C6A 115.9(2) . . ? C8A C7A H7A1 108.3 . . ? C6A C7A H7A1 108.3 . . ? C8A C7A H7A2 108.3 . . ? C6A C7A H7A2 108.3 . . ? H7A1 C7A H7A2 107.4 . . ? C7A C8A C9A 113.2(2) . . ? C7A C8A H8A1 108.9 . . ? C9A C8A H8A1 108.9 . . ? C7A C8A H8A2 108.9 . . ? C9A C8A H8A2 108.9 . . ? H8A1 C8A H8A2 107.8 . . ? C8A C9A H9A1 109.5 . . ? C8A C9A H9A2 109.5 . . ? H9A1 C9A H9A2 109.5 . . ? C8A C9A H9A3 109.5 . . ? H9A1 C9A H9A3 109.5 . . ? H9A2 C9A H9A3 109.5 . . ? C12 O11 C15 106.0(2) . . ? C12 O11 Li1 119.58(16) . . ? C15 O11 Li1 120.5(2) . . ? O11 C12 C13 106.4(2) . . ? O11 C12 H12A 110.4 . . ? C13 C12 H12A 110.4 . . ? O11 C12 H12B 110.4 . . ? C13 C12 H12B 110.4 . . ? H12A C12 H12B 108.6 . . ? C14 C13 C12 104.3(3) . . ? C14 C13 H13A 110.9 . . ? C12 C13 H13A 110.9 . . ? C14 C13 H13B 110.9 . . ? C12 C13 H13B 110.9 . . ? H13A C13 H13B 108.9 . . ? C15 C14 C13 106.3(3) . . ? C15 C14 H14A 110.5 . . ? C13 C14 H14A 110.5 . . ? C15 C14 H14B 110.5 . . ? C13 C14 H14B 110.5 . . ? H14A C14 H14B 108.7 . . ? O11 C15 C14 108.4(3) . . ? O11 C15 H15A 110.0 . . ? C14 C15 H15A 110.0 . . ? O11 C15 H15B 110.0 . . ? C14 C15 H15B 110.0 . . ? H15A C15 H15B 108.4 . . ? C25 O21 C22 108.46(16) . . ? C25 O21 Li1 121.84(12) . . ? C22 O21 Li1 116.82(14) . . ? O21 C22 C23 107.52(18) . . ? O21 C22 H22A 110.2 . . ? C23 C22 H22A 110.2 . . ? O21 C22 H22B 110.2 . . ? C23 C22 H22B 110.2 . . ? H22A C22 H22B 108.5 . . ? C22 C23 C24 103.2(2) . . ? C22 C23 H23A 111.1 . . ? C24 C23 H23A 111.1 . . ? C22 C23 H23B 111.1 . . ? C24 C23 H23B 111.1 . . ? H23A C23 H23B 109.1 . . ? C25 C24 C23 101.9(2) . . ? C25 C24 H24A 111.4 . . ? C23 C24 H24A 111.4 . . ? C25 C24 H24B 111.4 . . ? C23 C24 H24B 111.4 . . ? H24A C24 H24B 109.3 . . ? O21 C25 C24 105.34(14) . . ? O21 C25 H25A 110.7 . . ? C24 C25 H25A 110.7 . . ? O21 C25 H25B 110.7 . . ? C24 C25 H25B 110.7 . . ? H25A C25 H25B 108.8 . . ? C32 O31 C35 108.86(15) . . ? C32 O31 Li2 115.59(14) . . ? C35 O31 Li2 120.62(12) . . ? O31 C32 C33 106.69(17) . . ? O31 C32 H32A 110.4 . . ? C33 C32 H32A 110.4 . . ? O31 C32 H32B 110.4 . . ? C33 C32 H32B 110.4 . . ? H32A C32 H32B 108.6 . . ? C32 C33 C34 102.17(19) . . ? C32 C33 H33A 111.3 . . ? C34 C33 H33A 111.3 . . ? C32 C33 H33B 111.3 . . ? C34 C33 H33B 111.3 . . ? H33A C33 H33B 109.2 . . ? C33 C34 C35 102.4(2) . . ? C33 C34 H34A 111.3 . . ? C35 C34 H34A 111.3 . . ? C33 C34 H34B 111.3 . . ? C35 C34 H34B 111.3 . . ? H34A C34 H34B 109.2 . . ? O31 C35 C34 105.13(13) . . ? O31 C35 H35A 110.7 . . ? C34 C35 H35A 110.7 . . ? O31 C35 H35B 110.7 . . ? C34 C35 H35B 110.7 . . ? H35A C35 H35B 108.8 . . ? C45 O41 C42 107.38(19) . . ? C45 O41 Li2 126.25(18) . . ? C42 O41 Li2 123.81(18) . . ? O41 C42 C43 104.9(2) . . ? O41 C42 H42A 110.8 . . ? C43 C42 H42A 110.8 . . ? O41 C42 H42B 110.8 . . ? C43 C42 H42B 110.8 . . ? H42A C42 H42B 108.9 . . ? C44 C43 C42 105.6(2) . . ? C44 C43 H43A 110.6 . . ? C42 C43 H43A 110.6 . . ? C44 C43 H43B 110.6 . . ? C42 C43 H43B 110.6 . . ? H43A C43 H43B 108.8 . . ? C43 C44 C45 105.6(2) . . ? C43 C44 H44A 110.6 . . ? C45 C44 H44A 110.6 . . ? C43 C44 H44B 110.6 . . ? C45 C44 H44B 110.6 . . ? H44A C44 H44B 108.8 . . ? O41 C45 C44 107.1(2) . . ? O41 C45 H45A 110.3 . . ? C44 C45 H45A 110.3 . . ? O41 C45 H45B 110.3 . . ? C44 C45 H45B 110.3 . . ? H45A C45 H45B 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 O21 Li1 Li2 O31 -178.64(17) . . . . ? O11 Li1 Li2 O31 -3.5(3) . . . . ? O21 Li1 Li2 O41 7.6(3) . . . . ? O11 Li1 Li2 O41 -177.27(17) . . . . ? C3 C1 C2 C3 0.6(3) 2_656 . . . ? B1 C1 C2 C3 -177.89(17) . . . . ? C1 C2 C3 C1 -0.7(3) . . . 2_656 ? C1 C2 C3 C4 174.97(16) . . . . ? C2 C3 C4 C5 -85.17(17) . . . . ? C1 C3 C4 C5 90.4(2) 2_656 . . . ? C3 C4 C5 C6 -176.78(13) . . . . ? C4 C5 C6 C7 -173.46(12) . . . . ? C5 C6 C7 C8 178.51(14) . . . . ? C6 C7 C8 C9 70.7(2) . . . . ? C3A C1A C2A C3A -0.4(4) 2_565 . . . ? B1A C1A C2A C3A 178.97(18) . . . . ? C1A C2A C3A C1A 0.4(4) . . . 2_565 ? C1A C2A C3A C4A -177.00(18) . . . . ? C2A C3A C4A C5A 92.58(17) . . . . ? C1A C3A C4A C5A -84.8(2) 2_565 . . . ? C3A C4A C5A C6A 179.76(16) . . . . ? C4A C5A C6A C7A 173.02(13) . . . . ? C5A C6A C7A C8A 63.4(3) . . . . ? C6A C7A C8A C9A 65.0(4) . . . . ? O21 Li1 O11 C12 176.13(16) . . . . ? Li2 Li1 O11 C12 -0.1(3) . . . . ? O21 Li1 O11 C15 -49.2(2) . . . . ? Li2 Li1 O11 C15 134.5(2) . . . . ? C15 O11 C12 C13 28.7(2) . . . . ? Li1 O11 C12 C13 169.09(18) . . . . ? O11 C12 C13 C14 -17.8(3) . . . . ? C12 C13 C14 C15 0.3(4) . . . . ? C12 O11 C15 C14 -29.2(3) . . . . ? Li1 O11 C15 C14 -169.1(2) . . . . ? C13 C14 C15 O11 17.3(4) . . . . ? O11 Li1 O21 C25 167.32(15) . . . . ? Li2 Li1 O21 C25 -16.5(3) . . . . ? O11 Li1 O21 C22 -55.6(2) . . . . ? Li2 Li1 O21 C22 120.51(19) . . . . ? C25 O21 C22 C23 3.9(3) . . . . ? Li1 O21 C22 C23 -138.5(2) . . . . ? O21 C22 C23 C24 -25.1(3) . . . . ? C22 C23 C24 C25 35.6(3) . . . . ? C22 O21 C25 C24 19.3(3) . . . . ? Li1 O21 C25 C24 159.4(2) . . . . ? C23 C24 C25 O21 -34.0(3) . . . . ? O41 Li2 O31 C32 56.2(2) . . . . ? Li1 Li2 O31 C32 -118.98(18) . . . . ? O41 Li2 O31 C35 -169.35(14) . . . . ? Li1 Li2 O31 C35 15.4(3) . . . . ? C35 O31 C32 C33 -9.0(3) . . . . ? Li2 O31 C32 C33 130.5(2) . . . . ? O31 C32 C33 C34 29.5(3) . . . . ? C32 C33 C34 C35 -37.8(3) . . . . ? C32 O31 C35 C34 -15.3(3) . . . . ? Li2 O31 C35 C34 -152.4(2) . . . . ? C33 C34 C35 O31 33.3(3) . . . . ? O31 Li2 O41 C45 -153.09(16) . . . . ? Li1 Li2 O41 C45 22.3(3) . . . . ? O31 Li2 O41 C42 47.4(2) . . . . ? Li1 Li2 O41 C42 -137.2(2) . . . . ? C45 O41 C42 C43 31.9(2) . . . . ? Li2 O41 C42 C43 -165.3(2) . . . . ? O41 C42 C43 C44 -25.6(4) . . . . ? C42 C43 C44 C45 10.2(4) . . . . ? C42 O41 C45 C44 -25.7(2) . . . . ? Li2 O41 C45 C44 172.0(2) . . . . ? C43 C44 C45 O41 8.9(3) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.233 _refine_diff_density_min -0.196 _refine_diff_density_rms 0.044