# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2007 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Jim Mayer' _publ_contact_author_address ; Department of Chemistry, BOX 351700 University of Washington Seattle, WA 98195 USA ; _publ_contact_author_email mayer@chem.washington.edu _publ_section_title ; The First Crystal Structure of a Monomeric Phenoxyl Radical: 2,4,6-Tri-tert-butylphenoxyl Radical ; _publ_section_abstract ; Crystals have been obtained of 2,4,6-tri-tert-butylphenoxyl radical. ; _publ_section_comment ; The tert-butyl group in the 4-position is disordered. ; _publ_section_exptl_prep ; tBu3PhO was crystallized in dry acetonitrile at -30 C. ; _publ_section_exptl_refinement ; All H atoms were initially located in a difference Fourier map and were refined with a riding model. H atoms were placed in geometrically idealised positions and constrained to ride on their parent atoms with C---H distances in the range 0.95-1.00 \%A. U~iso~ values were fixed such that they were 1.2U~eq~ of their parent atom U~eq~ for CH's and 1.5U~eq~ of their parent atom U~eq~ in case of methyl groups. ; _publ_section_references ; Altomare, A.; Cascarano, G.; Giacovazzo, C.; Burla, M.C.; Polidori, G.; Camalli, M. (1994) J. Appl. Cryst. 27, 435-442. Beurskens, P.T., Admiraal, G., Beurskens, G., Bosman, W. P., Garcia-Granada, S., Gould, R. O., Smits, J. M. M. & Smykalla, C. (1996) The DIRDIF96 Program System. Technical Report of the Crystallography Laboratory, University of Nijmegen, The Netherlands. MacKay, S.; Gilmore, C.J.; Edwards, C.; Tremayne, M.; Stewart, N.; Shankland, K. (1998) "maXus: a computer program for the solution and refinement of crystal structures from diffraction data" University of Glasgow, Scotland, UK, Nonius BV, Delft, The Netherlands and MacScience Co. Ltd., Yokohama, Japan. Otwinowski, Z.; Minor, W. (1996) Methods in Enzymology, 276, 307-326. Sheldrick, G. M. (1997) SHELXL97 University of G\"ottingen, Germany. ; loop_ _publ_author_name 'James Mayer' 'John Freudenthal' 'Virginia W. Manner' 'Todd F. Markle' 'Justine Roth' data_shelxl _database_code_depnum_ccdc_archive 'CCDC 658150' _audit_creation_method SHELXL-97 _chemical_name_systematic ; tBu3PhO ; _chemical_name_common tBu3PhO _chemical_melting_point ? _chemical_formula_moiety 'C18 H29 O1' _chemical_formula_sum 'C18 H29 O' _chemical_formula_weight 261.41 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_space_group_name_H-M 'c 2/c' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_Hall '-c 2yc' _symmetry_Int_Tables_number 15 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 15.6814(7) _cell_length_b 9.5268(5) _cell_length_c 11.3995(5) _cell_angle_alpha 90.00 _cell_angle_beta 94.948(3) _cell_angle_gamma 90.00 _cell_volume 1696.58(14) _cell_formula_units_Z 4 _cell_measurement_temperature 130(2) _cell_measurement_reflns_used 84 _exptl_crystal_description cut-block _exptl_crystal_colour blue _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.023 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 580 _exptl_absorpt_coefficient_mu 0.061 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9940 _exptl_absorpt_correction_T_max 0.9940 _exptl_absorpt_process_details HKL2000 _exptl_special_details ; Data was collected with \w and \f scans in 1^o^ increments with 30 second exposures per degree. Crystal-to-detector distance was 30 mm. 21990 full and partial reflection were integrated. ; _diffrn_ambient_temperature 130(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 'Nonius KappaCCD' _diffrn_measurement_method '\f and \w scans' _diffrn_reflns_number 3809 _diffrn_reflns_av_R_equivalents 0.0780 _diffrn_reflns_av_sigmaI/netI 0.0817 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.50 _diffrn_reflns_theta_max 28.47 _reflns_number_total 2037 _reflns_number_gt 1322 _reflns_threshold_expression >2sigma(I) _computing_data_collection KappaCCD _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'maXus, Zortep' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2037 _refine_ls_number_parameters 105 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0899 _refine_ls_R_factor_gt 0.0569 _refine_ls_wR_factor_ref 0.1675 _refine_ls_wR_factor_gt 0.1471 _refine_ls_goodness_of_fit_ref 0.985 _refine_ls_restrained_S_all 0.985 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.5000 0.67893(12) 0.2500 0.0328(4) Uani 1 2 d S . . C1 C 0.5000 0.54818(17) 0.2500 0.0220(4) Uani 1 2 d S . . C2 C 0.42877(7) 0.46929(13) 0.18881(8) 0.0232(3) Uani 1 1 d . . . C3 C 0.43190(7) 0.32591(14) 0.19180(9) 0.0282(3) Uani 1 1 d . . . H3 H 0.3858 0.2749 0.1526 0.034 Uiso 1 1 d R . . C4 C 0.5000 0.25016(18) 0.2500 0.0305(4) Uani 1 2 d S . . C5 C 0.35449(7) 0.54916(14) 0.12425(9) 0.0294(4) Uani 1 1 d . . . C6 C 0.38758(8) 0.63787(18) 0.02485(10) 0.0427(4) Uani 1 1 d . . . H6A H 0.4297 0.7059 0.0585 0.051 Uiso 1 1 d R . . H6B H 0.3396 0.6879 -0.0172 0.051 Uiso 1 1 d R . . H6C H 0.4145 0.5762 -0.0301 0.051 Uiso 1 1 d R . . C7 C 0.31156(8) 0.64391(15) 0.21128(11) 0.0370(4) Uani 1 1 d . . . H7A H 0.2914 0.5863 0.2746 0.044 Uiso 1 1 d R . . H7B H 0.2629 0.6928 0.1699 0.044 Uiso 1 1 d R . . H7C H 0.3531 0.7129 0.2449 0.044 Uiso 1 1 d R . . C8 C 0.28582(9) 0.44985(16) 0.06828(12) 0.0447(4) Uani 1 1 d . . . H8A H 0.3116 0.3866 0.0135 0.054 Uiso 1 1 d R . . H8B H 0.2403 0.5047 0.0255 0.054 Uiso 1 1 d R . . H8C H 0.2617 0.3947 0.1300 0.054 Uiso 1 1 d R . . C9 C 0.5000 0.09011(19) 0.2500 0.0396(5) Uani 1 2 d S . . C10 C 0.4826(3) 0.0352(3) 0.3601(3) 0.0471(8) Uani 0.50 1 d P A -2 H10A H 0.4796 -0.0674 0.3554 0.071 Uiso 0.50 1 calc PR A -2 H10B H 0.4278 0.0722 0.3819 0.071 Uiso 0.50 1 calc PR A -2 H10C H 0.5283 0.0627 0.4198 0.071 Uiso 0.50 1 calc PR A -2 C11 C 0.41658(17) 0.0323(3) 0.1552(3) 0.0382(6) Uani 0.50 1 d P A -2 H11A H 0.4213 -0.0695 0.1448 0.057 Uiso 0.50 1 calc PR A -2 H11B H 0.4185 0.0790 0.0789 0.057 Uiso 0.50 1 calc PR A -2 H11C H 0.3623 0.0542 0.1878 0.057 Uiso 0.50 1 calc PR A -2 C12 C 0.57442(18) 0.0355(3) 0.1909(3) 0.0368(7) Uani 0.50 1 d P A -2 H12A H 0.6276 0.0598 0.2379 0.055 Uiso 0.50 1 calc PR A -2 H12B H 0.5746 0.0775 0.1125 0.055 Uiso 0.50 1 calc PR A -2 H12C H 0.5700 -0.0668 0.1835 0.055 Uiso 0.50 1 calc PR A -2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0281(7) 0.0197(7) 0.0492(7) 0.000 -0.0045(5) 0.000 C1 0.0227(8) 0.0204(9) 0.0233(8) 0.000 0.0041(6) 0.000 C2 0.0237(6) 0.0252(8) 0.0208(6) -0.0002(4) 0.0031(4) -0.0033(5) C3 0.0317(7) 0.0246(8) 0.0297(6) -0.0062(5) 0.0101(5) -0.0088(5) C4 0.0389(10) 0.0200(10) 0.0358(9) 0.000 0.0213(7) 0.000 C5 0.0222(6) 0.0385(9) 0.0266(6) 0.0054(5) -0.0027(5) -0.0033(5) C6 0.0338(8) 0.0573(10) 0.0362(7) 0.0177(7) -0.0006(6) 0.0021(6) C7 0.0247(7) 0.0451(9) 0.0404(7) 0.0030(6) -0.0019(5) 0.0057(6) C8 0.0337(8) 0.0607(11) 0.0379(7) -0.0023(6) -0.0072(6) -0.0120(7) C9 0.0466(12) 0.0176(10) 0.0589(12) 0.000 0.0296(9) 0.000 C10 0.079(2) 0.0253(16) 0.0392(15) 0.0053(12) 0.0190(16) 0.0008(16) C11 0.0348(14) 0.0194(14) 0.0591(16) -0.0081(12) -0.0032(12) -0.0014(11) C12 0.0305(15) 0.0210(15) 0.0594(18) -0.0044(12) 0.0073(13) 0.0015(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.246(2) . ? C1 C2 1.4713(14) 2_655 ? C1 C2 1.4713(14) . ? C2 C3 1.3673(18) . ? C2 C5 1.5261(16) . ? C3 C4 1.4068(15) . ? C3 H3 0.9500 . ? C4 C3 1.4068(15) 2_655 ? C4 C9 1.525(2) . ? C5 C8 1.5308(18) . ? C5 C7 1.5387(18) . ? C5 C6 1.5390(17) . ? C6 H6A 0.9800 . ? C6 H6B 0.9799 . ? C6 H6C 0.9801 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 H8A 0.9800 . ? C8 H8B 0.9801 . ? C8 H8C 0.9800 . ? C9 C10 1.408(3) . ? C9 C10 1.408(3) 2_655 ? C9 C12 1.491(3) 2_655 ? C9 C12 1.491(3) . ? C9 C11 1.714(3) . ? C9 C11 1.714(3) 2_655 ? 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 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 C2 120.72(8) . 2_655 ? O1 C1 C2 120.72(8) . . ? C2 C1 C2 118.56(15) 2_655 . ? C3 C2 C1 118.32(11) . . ? C3 C2 C5 122.31(10) . . ? C1 C2 C5 119.38(12) . . ? C2 C3 C4 123.27(11) . . ? C2 C3 H3 118.3 . . ? C4 C3 H3 118.4 . . ? C3 C4 C3 118.27(16) 2_655 . ? C3 C4 C9 120.86(8) 2_655 . ? C3 C4 C9 120.86(8) . . ? C2 C5 C8 111.90(12) . . ? C2 C5 C7 109.86(9) . . ? C8 C5 C7 107.47(10) . . ? C2 C5 C6 109.70(9) . . ? C8 C5 C6 107.59(10) . . ? C7 C5 C6 110.27(12) . . ? C5 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C5 C6 H6C 109.4 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C5 C7 H7A 109.5 . . ? C5 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C5 C7 H7C 109.4 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C5 C8 H8A 109.4 . . ? C5 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C5 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C10 C9 C10 136.4(3) . 2_655 ? C10 C9 C12 41.26(17) . 2_655 ? C10 C9 C12 119.50(18) 2_655 2_655 ? C10 C9 C12 119.50(18) . . ? C10 C9 C12 41.26(17) 2_655 . ? C12 C9 C12 139.1(2) 2_655 . ? C10 C9 C4 111.80(14) . . ? C10 C9 C4 111.80(14) 2_655 . ? C12 C9 C4 110.43(12) 2_655 . ? C12 C9 C4 110.43(12) . . ? C10 C9 C11 104.3(2) . . ? C10 C9 C11 60.96(19) 2_655 . ? C12 C9 C11 65.66(16) 2_655 . ? C12 C9 C11 100.82(17) . . ? C4 C9 C11 108.75(11) . . ? C10 C9 C11 60.96(19) . 2_655 ? C10 C9 C11 104.3(2) 2_655 2_655 ? C12 C9 C11 100.81(17) 2_655 2_655 ? C12 C9 C11 65.66(16) . 2_655 ? C4 C9 C11 108.75(11) . 2_655 ? C11 C9 C11 142.5(2) . 2_655 ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C9 C11 H11A 109.5 . . ? C9 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C9 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C9 C12 H12A 109.5 . . ? C9 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C9 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.950 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.389 _refine_diff_density_min -0.200 _refine_diff_density_rms 0.047 #===END data_2 _database_code_depnum_ccdc_archive 'CCDC 658151' _audit_creation_method SHELXL-97 _chemical_name_systematic ; tBu3PhOH ; _chemical_name_common tBu3PhOH _chemical_melting_point ? _chemical_formula_moiety 'C18 H27.99 O0.99' _chemical_formula_sum 'C18 H27.99 O0.99' _chemical_formula_weight 260.23 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_space_group_name_H-M c2/c _symmetry_cell_setting Monoclinic _symmetry_space_group_name_Hall -c_2yc _symmetry_Int_Tables_number 15 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 10.0648(5) _cell_length_b 17.4311(9) _cell_length_c 19.6355(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.185(3) _cell_angle_gamma 90.00 _cell_volume 3444.8(3) _cell_formula_units_Z 8 _cell_measurement_temperature 130(2) _cell_measurement_reflns_used 82 _exptl_crystal_description cut-block _exptl_crystal_colour clear _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.003 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1151 _exptl_absorpt_coefficient_mu 0.060 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9947 _exptl_absorpt_correction_T_max 0.9947 _exptl_absorpt_process_details HKL2000 _exptl_special_details ; Data was collected with \w and \f scans in 2^o^ increments with 60 second exposures per degree. Crystal-to-detector distance was 30 mm. 24564 full and partial reflection were integrated. ; _diffrn_ambient_temperature 130(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 'Nonius KappaCCD' _diffrn_measurement_method '\f and \w scans' _diffrn_reflns_number 6571 _diffrn_reflns_av_R_equivalents 0.0623 _diffrn_reflns_av_sigmaI/netI 0.0854 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.07 _diffrn_reflns_theta_max 26.96 _reflns_number_total 3479 _reflns_number_gt 1388 _reflns_threshold_expression >2sigma(I) _computing_data_collection KappaCCD _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'maXus, Zortep' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. Size of data was cut due to signal to noise ratio on the detector. Three one-third site occupancies give 0.99 for oxygen and 27.99 for hydrogens. All three tert-butyl groups are disordered. ; _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^)+(0.0950P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3479 _refine_ls_number_parameters 292 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1640 _refine_ls_R_factor_gt 0.0643 _refine_ls_wR_factor_ref 0.1983 _refine_ls_wR_factor_gt 0.1479 _refine_ls_goodness_of_fit_ref 0.944 _refine_ls_restrained_S_all 0.944 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.4683(4) 0.3050(2) 0.62529(19) 0.0481(10) Uani 0.33 1 d P . . H1 H 0.5310 0.3030 0.5972 0.072 Uiso 0.33 1 calc PR . . O2 O 0.0596(4) 0.1642(3) 0.6234(2) 0.0522(10) Uani 0.33 1 d P . . H2 H 0.0302 0.2078 0.6131 0.078 Uiso 0.33 1 calc PR . . O3 O 0.4688(4) 0.0296(2) 0.6269(2) 0.0502(11) Uani 0.33 1 d P . . H3 H 0.5445 0.0358 0.6099 0.075 Uiso 0.33 1 calc PR . . C1 C 0.40026(19) 0.23582(12) 0.62496(9) 0.0417(5) Uani 1 1 d . . . C2 C 0.2621(2) 0.23676(11) 0.62337(9) 0.0428(5) Uani 1 1 d . B . C3 C 0.19488(18) 0.16580(13) 0.62352(9) 0.0454(5) Uani 1 1 d . . . C4 C 0.2630(2) 0.09594(11) 0.62523(9) 0.0449(6) Uani 1 1 d . C . C5 C 0.4019(2) 0.09816(12) 0.62665(9) 0.0449(6) Uani 1 1 d . . . C6 C 0.47335(18) 0.16703(12) 0.62640(8) 0.0436(5) Uani 1 1 d . A . C7 C 0.62616(19) 0.16796(14) 0.62807(10) 0.0501(5) Uani 1 1 d . . . C8 C 0.1842(2) 0.31274(12) 0.62181(10) 0.0498(6) Uani 1 1 d . . . C9 C 0.1877(2) 0.01960(12) 0.62488(11) 0.0578(7) Uani 1 1 d . . . C10 C 0.6747(4) 0.2096(3) 0.6933(2) 0.0558(12) Uani 0.50 1 d P A -2 H10A H 0.7720 0.2091 0.6948 0.084 Uiso 0.50 1 calc PR A -2 H10B H 0.6398 0.1832 0.7335 0.084 Uiso 0.50 1 calc PR A -2 H10C H 0.6430 0.2627 0.6929 0.084 Uiso 0.50 1 calc PR A -2 C12 C 0.6805(4) 0.2059(3) 0.5644(2) 0.0546(12) Uani 0.50 1 d P A -2 H12A H 0.7775 0.2090 0.5676 0.082 Uiso 0.50 1 calc PR A -2 H12B H 0.6434 0.2577 0.5601 0.082 Uiso 0.50 1 calc PR A -2 H12C H 0.6556 0.1755 0.5243 0.082 Uiso 0.50 1 calc PR A -2 C14 C 0.6807(4) 0.0867(3) 0.6310(2) 0.0592(12) Uani 0.50 1 d P A -2 H14A H 0.6522 0.0584 0.5904 0.089 Uiso 0.50 1 calc PR A -2 H14B H 0.6472 0.0609 0.6718 0.089 Uiso 0.50 1 calc PR A -2 H14C H 0.7780 0.0885 0.6327 0.089 Uiso 0.50 1 calc PR A -2 C11 C 0.6820(5) 0.2503(3) 0.6256(3) 0.0818(16) Uani 0.50 1 d P A -3 H11A H 0.7788 0.2487 0.6309 0.123 Uiso 0.50 1 calc PR A -3 H11B H 0.6433 0.2806 0.6625 0.123 Uiso 0.50 1 calc PR A -3 H11C H 0.6594 0.2738 0.5817 0.123 Uiso 0.50 1 calc PR A -3 C13 C 0.6832(5) 0.1291(4) 0.5642(3) 0.0809(16) Uani 0.50 1 d P A -3 H13A H 0.6475 0.1541 0.5234 0.121 Uiso 0.50 1 calc PR A -3 H13B H 0.6583 0.0747 0.5640 0.121 Uiso 0.50 1 calc PR A -3 H13C H 0.7803 0.1336 0.5645 0.121 Uiso 0.50 1 calc PR A -3 C15 C 0.6805(5) 0.1307(4) 0.6920(3) 0.0781(16) Uani 0.50 1 d P A -3 H15A H 0.7777 0.1345 0.6922 0.117 Uiso 0.50 1 calc PR A -3 H15B H 0.6544 0.0766 0.6930 0.117 Uiso 0.50 1 calc PR A -3 H15C H 0.6448 0.1570 0.7321 0.117 Uiso 0.50 1 calc PR A -3 C16 C 0.0970(5) 0.3211(3) 0.6857(2) 0.0703(14) Uani 0.50 1 d P B -2 H16A H 0.0301 0.2803 0.6862 0.105 Uiso 0.50 1 calc PR B -2 H16B H 0.0527 0.3711 0.6850 0.105 Uiso 0.50 1 calc PR B -2 H16C H 0.1529 0.3171 0.7265 0.105 Uiso 0.50 1 calc PR B -2 C18 C 0.1009(5) 0.3192(3) 0.5568(2) 0.0653(13) Uani 0.50 1 d P B -2 H18A H 0.1594 0.3172 0.5170 0.098 Uiso 0.50 1 calc PR B -2 H18B H 0.0525 0.3680 0.5569 0.098 Uiso 0.50 1 calc PR B -2 H18C H 0.0374 0.2767 0.5548 0.098 Uiso 0.50 1 calc PR B -2 C20 C 0.2802(5) 0.3816(3) 0.6235(3) 0.0665(13) Uani 0.50 1 d P B -2 H20A H 0.3315 0.3807 0.6660 0.100 Uiso 0.50 1 calc PR B -2 H20B H 0.2292 0.4295 0.6209 0.100 Uiso 0.50 1 calc PR B -2 H20C H 0.3409 0.3786 0.5846 0.100 Uiso 0.50 1 calc PR B -2 C17 C 0.0322(5) 0.2995(3) 0.6195(3) 0.0687(14) Uani 0.50 1 d P B -3 H17A H 0.0090 0.2710 0.5781 0.103 Uiso 0.50 1 calc PR B -3 H17B H -0.0136 0.3491 0.6192 0.103 Uiso 0.50 1 calc PR B -3 H17C H 0.0050 0.2700 0.6596 0.103 Uiso 0.50 1 calc PR B -3 C19 C 0.2172(5) 0.3589(3) 0.5574(2) 0.0670(14) Uani 0.50 1 d P B -3 H19A H 0.3106 0.3748 0.5589 0.101 Uiso 0.50 1 calc PR B -3 H19B H 0.1603 0.4045 0.5552 0.101 Uiso 0.50 1 calc PR B -3 H19C H 0.2019 0.3270 0.5171 0.101 Uiso 0.50 1 calc PR B -3 C21 C 0.2124(6) 0.3609(3) 0.6852(2) 0.0673(14) Uani 0.50 1 d P B -3 H21A H 0.1870 0.3319 0.7259 0.101 Uiso 0.50 1 calc PR B -3 H21B H 0.1609 0.4086 0.6830 0.101 Uiso 0.50 1 calc PR B -3 H21C H 0.3073 0.3731 0.6874 0.101 Uiso 0.50 1 calc PR B -3 C22 C 0.2212(6) -0.0270(3) 0.6878(2) 0.0683(14) Uani 0.50 1 d P C -2 H22A H 0.1760 -0.0768 0.6854 0.102 Uiso 0.50 1 calc PR C -2 H22B H 0.1917 0.0006 0.7285 0.102 Uiso 0.50 1 calc PR C -2 H22C H 0.3174 -0.0351 0.6902 0.102 Uiso 0.50 1 calc PR C -2 C24 C 0.2315(5) -0.0276(3) 0.5581(2) 0.0652(14) Uani 0.50 1 d P C -2 H24A H 0.1821 -0.0760 0.5560 0.098 Uiso 0.50 1 calc PR C -2 H24B H 0.3270 -0.0384 0.5603 0.098 Uiso 0.50 1 calc PR C -2 H24C H 0.2122 0.0029 0.5173 0.098 Uiso 0.50 1 calc PR C -2 C26 C 0.0394(5) 0.0314(3) 0.6187(3) 0.0682(14) Uani 0.50 1 d P C -2 H26A H 0.0196 0.0591 0.5764 0.102 Uiso 0.50 1 calc PR C -2 H26B H 0.0077 0.0613 0.6576 0.102 Uiso 0.50 1 calc PR C -2 H26C H -0.0052 -0.0186 0.6179 0.102 Uiso 0.50 1 calc PR C -2 C23 C 0.2809(6) -0.0480(3) 0.6308(3) 0.0845(17) Uani 0.50 1 d P C -3 H23A H 0.2295 -0.0958 0.6297 0.127 Uiso 0.50 1 calc PR C -3 H23B H 0.3302 -0.0448 0.6738 0.127 Uiso 0.50 1 calc PR C -3 H23C H 0.3434 -0.0474 0.5926 0.127 Uiso 0.50 1 calc PR C -3 C25 C 0.1018(6) 0.0105(3) 0.5630(3) 0.0811(16) Uani 0.50 1 d P C -3 H25A H 0.0553 -0.0389 0.5651 0.122 Uiso 0.50 1 calc PR C -3 H25B H 0.1573 0.0120 0.5221 0.122 Uiso 0.50 1 calc PR C -3 H25C H 0.0367 0.0522 0.5612 0.122 Uiso 0.50 1 calc PR C -3 C27 C 0.0967(5) 0.0162(3) 0.6914(3) 0.0794(16) Uani 0.50 1 d P C -3 H27A H 0.0326 0.0584 0.6904 0.119 Uiso 0.50 1 calc PR C -3 H27B H 0.1528 0.0208 0.7321 0.119 Uiso 0.50 1 calc PR C -3 H27C H 0.0490 -0.0328 0.6926 0.119 Uiso 0.50 1 calc PR C -3 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.045(3) 0.049(3) 0.050(3) -0.0017(19) 0.0103(18) -0.011(2) O2 0.038(2) 0.051(3) 0.067(3) 0.000(2) -0.0087(19) 0.000(2) O3 0.044(3) 0.048(3) 0.058(3) 0.0068(19) 0.001(2) 0.003(2) C1 0.0407(13) 0.0441(13) 0.0402(11) -0.0016(9) 0.0027(9) 0.0000(10) C2 0.0455(13) 0.0437(13) 0.0391(12) 0.0004(9) -0.0005(9) 0.0047(10) C3 0.0440(12) 0.0492(13) 0.0431(11) -0.0014(10) -0.0053(8) -0.0002(11) C4 0.0473(14) 0.0433(14) 0.0443(12) 0.0014(9) 0.0000(9) -0.0017(10) C5 0.0471(14) 0.0427(14) 0.0449(13) 0.0042(9) -0.0007(9) 0.0009(10) C6 0.0419(11) 0.0502(12) 0.0387(11) 0.0022(10) -0.0013(8) 0.0019(12) C7 0.0399(12) 0.0601(14) 0.0502(12) 0.0008(11) 0.0023(9) 0.0030(12) C8 0.0518(13) 0.0488(16) 0.0488(12) -0.0019(9) -0.0014(10) 0.0078(10) C9 0.0587(16) 0.0476(16) 0.0670(16) 0.0026(11) -0.0062(11) -0.0062(11) C10 0.042(3) 0.077(4) 0.048(3) -0.005(2) -0.005(2) -0.004(3) C12 0.041(3) 0.075(4) 0.048(3) -0.004(2) 0.0058(19) -0.005(3) C14 0.044(3) 0.084(4) 0.050(3) -0.002(2) -0.004(2) 0.014(2) C11 0.055(3) 0.082(4) 0.109(5) 0.011(3) -0.007(3) -0.008(3) C13 0.060(3) 0.109(5) 0.074(4) 0.010(3) 0.014(3) 0.013(4) C15 0.050(3) 0.110(5) 0.074(4) 0.018(3) -0.003(2) 0.016(3) C16 0.062(3) 0.085(4) 0.063(3) -0.010(3) -0.003(2) 0.022(3) C18 0.067(3) 0.068(4) 0.060(3) 0.003(2) -0.013(2) 0.019(3) C20 0.078(4) 0.045(3) 0.077(3) -0.005(2) -0.002(3) 0.011(3) C17 0.058(3) 0.073(4) 0.075(3) 0.004(3) -0.007(3) 0.014(3) C19 0.089(4) 0.054(3) 0.058(3) 0.005(2) 0.006(3) 0.014(3) C21 0.084(4) 0.063(4) 0.054(3) -0.010(2) 0.001(3) 0.017(3) C22 0.091(4) 0.047(3) 0.067(3) 0.013(2) 0.007(3) -0.013(3) C24 0.079(4) 0.046(3) 0.070(3) -0.006(2) -0.012(3) -0.002(3) C26 0.062(4) 0.064(3) 0.078(4) -0.005(3) -0.008(3) -0.023(3) C23 0.083(4) 0.048(4) 0.123(5) 0.014(3) -0.005(4) -0.012(3) C25 0.089(4) 0.080(4) 0.074(4) -0.001(3) -0.025(3) -0.029(4) C27 0.074(4) 0.077(4) 0.088(4) 0.014(3) -0.008(3) -0.024(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.386(4) . ? O1 H1 0.8400 . ? O2 C3 1.362(4) . ? O2 H2 0.8400 . ? O3 C5 1.371(4) . ? O3 H3 0.8400 . ? C1 C2 1.391(3) . ? C1 C6 1.407(3) . ? C2 C3 1.410(3) . ? C2 C8 1.539(3) . ? C3 C4 1.398(3) . ? C4 C5 1.399(3) . ? C4 C9 1.532(3) . ? C5 C6 1.400(3) . ? C6 C7 1.538(3) . ? C7 C15 1.514(5) . ? C7 C12 1.518(5) . ? C7 C14 1.520(5) . ? C7 C13 1.539(5) . ? C7 C11 1.542(5) . ? C7 C10 1.550(4) . ? C8 C21 1.528(5) . ? C8 C18 1.529(4) . ? C8 C19 1.536(5) . ? C8 C16 1.540(5) . ? C8 C20 1.542(5) . ? C8 C17 1.547(5) . ? C9 C25 1.498(5) . ? C9 C26 1.510(5) . ? C9 C23 1.511(6) . ? C9 C22 1.515(5) . ? C9 C27 1.599(5) . ? C9 C24 1.611(5) . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 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 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 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 C1 O1 H1 109.5 . . ? C3 O2 H2 109.5 . . ? C5 O3 H3 109.5 . . ? O1 C1 C2 118.9(2) . . ? O1 C1 C6 118.9(2) . . ? C2 C1 C6 122.22(18) . . ? C1 C2 C3 117.99(18) . . ? C1 C2 C8 121.32(18) . . ? C3 C2 C8 120.69(18) . . ? O2 C3 C4 118.2(3) . . ? O2 C3 C2 119.9(3) . . ? C4 C3 C2 121.94(17) . . ? C3 C4 C5 117.82(18) . . ? C3 C4 C9 120.92(18) . . ? C5 C4 C9 121.26(18) . . ? O3 C5 C4 117.8(2) . . ? O3 C5 C6 119.7(2) . . ? C4 C5 C6 122.50(18) . . ? C5 C6 C1 117.54(17) . . ? C5 C6 C7 121.52(19) . . ? C1 C6 C7 120.94(19) . . ? C15 C7 C12 137.7(3) . . ? C15 C7 C14 55.9(3) . . ? C12 C7 C14 107.8(3) . . ? C15 C7 C6 111.8(2) . . ? C12 C7 C6 110.5(2) . . ? C14 C7 C6 110.6(2) . . ? C15 C7 C13 110.6(4) . . ? C12 C7 C13 52.0(3) . . ? C14 C7 C13 59.0(3) . . ? C6 C7 C13 110.7(2) . . ? C15 C7 C11 107.1(3) . . ? C12 C7 C11 55.7(3) . . ? C14 C7 C11 137.4(3) . . ? C6 C7 C11 112.0(3) . . ? C13 C7 C11 104.3(3) . . ? C15 C7 C10 53.3(3) . . ? C12 C7 C10 111.3(3) . . ? C14 C7 C10 107.0(3) . . ? C6 C7 C10 109.6(2) . . ? C13 C7 C10 139.7(3) . . ? C11 C7 C10 58.5(3) . . ? C21 C8 C18 137.7(3) . . ? C21 C8 C19 110.0(3) . . ? C18 C8 C19 52.7(2) . . ? C21 C8 C2 111.3(2) . . ? C18 C8 C2 111.0(2) . . ? C19 C8 C2 110.8(2) . . ? C21 C8 C16 52.3(3) . . ? C18 C8 C16 111.2(3) . . ? C19 C8 C16 138.3(3) . . ? C2 C8 C16 110.9(2) . . ? C21 C8 C20 55.9(3) . . ? C18 C8 C20 107.6(3) . . ? C19 C8 C20 58.1(3) . . ? C2 C8 C20 110.5(2) . . ? C16 C8 C20 105.5(3) . . ? C21 C8 C17 106.7(3) . . ? C18 C8 C17 56.4(3) . . ? C19 C8 C17 105.7(3) . . ? C2 C8 C17 112.1(2) . . ? C16 C8 C17 58.2(3) . . ? C20 C8 C17 137.4(3) . . ? C25 C9 C26 51.8(3) . . ? C25 C9 C23 109.6(4) . . ? C26 C9 C23 136.5(3) . . ? C25 C9 C22 136.9(3) . . ? C26 C9 C22 110.8(3) . . ? C23 C9 C22 51.9(3) . . ? C25 C9 C4 112.4(3) . . ? C26 C9 C4 111.8(2) . . ? C23 C9 C4 111.7(3) . . ? C22 C9 C4 110.7(2) . . ? C25 C9 C27 109.2(4) . . ? C26 C9 C27 60.2(3) . . ? C23 C9 C27 105.4(3) . . ? C22 C9 C27 56.0(3) . . ? C4 C9 C27 108.3(2) . . ? C25 C9 C24 56.2(3) . . ? C26 C9 C24 106.1(3) . . ? C23 C9 C24 59.5(3) . . ? C22 C9 C24 109.2(3) . . ? C4 C9 C24 108.1(2) . . ? C27 C9 C24 143.6(3) . . ? C7 C10 H10A 109.5 . . ? C7 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C7 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C7 C12 H12A 109.5 . . ? C7 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C7 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C7 C14 H14A 109.5 . . ? C7 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C7 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C7 C11 H11A 109.5 . . ? C7 C11 H11B 109.5 . . ? C7 C11 H11C 109.5 . . ? C7 C13 H13A 109.5 . . ? C7 C13 H13B 109.5 . . ? C7 C13 H13C 109.5 . . ? C7 C15 H15A 109.5 . . ? C7 C15 H15B 109.5 . . ? C7 C15 H15C 109.5 . . ? C8 C16 H16A 109.5 . . ? C8 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C8 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C8 C18 H18A 109.5 . . ? C8 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C8 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C8 C20 H20A 109.5 . . ? C8 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C8 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C8 C17 H17A 109.5 . . ? C8 C17 H17B 109.5 . . ? C8 C17 H17C 109.5 . . ? C8 C19 H19A 109.5 . . ? C8 C19 H19B 109.5 . . ? C8 C19 H19C 109.5 . . ? C8 C21 H21A 109.5 . . ? C8 C21 H21B 109.5 . . ? C8 C21 H21C 109.5 . . ? C9 C22 H22A 109.5 . . ? C9 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C9 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C9 C24 H24A 109.5 . . ? C9 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C9 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C9 C26 H26A 109.5 . . ? C9 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C9 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C9 C23 H23A 109.5 . . ? C9 C23 H23B 109.5 . . ? C9 C23 H23C 109.5 . . ? C9 C25 H25A 109.5 . . ? C9 C25 H25B 109.5 . . ? C9 C25 H25C 109.5 . . ? C9 C27 H27A 109.5 . . ? C9 C27 H27B 109.5 . . ? C9 C27 H27C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 C3 -179.6(2) . . . . ? C6 C1 C2 C3 0.3(3) . . . . ? O1 C1 C2 C8 0.1(3) . . . . ? C6 C1 C2 C8 -179.99(16) . . . . ? C1 C2 C3 O2 178.6(2) . . . . ? C8 C2 C3 O2 -1.1(3) . . . . ? C1 C2 C3 C4 0.0(3) . . . . ? C8 C2 C3 C4 -179.71(17) . . . . ? O2 C3 C4 C5 -178.8(2) . . . . ? C2 C3 C4 C5 -0.2(3) . . . . ? O2 C3 C4 C9 1.8(3) . . . . ? C2 C3 C4 C9 -179.60(18) . . . . ? C3 C4 C5 O3 -178.6(2) . . . . ? C9 C4 C5 O3 0.8(3) . . . . ? C3 C4 C5 C6 0.0(3) . . . . ? C9 C4 C5 C6 179.43(17) . . . . ? O3 C5 C6 C1 178.9(2) . . . . ? C4 C5 C6 C1 0.3(3) . . . . ? O3 C5 C6 C7 -1.5(3) . . . . ? C4 C5 C6 C7 179.93(16) . . . . ? O1 C1 C6 C5 179.4(2) . . . . ? C2 C1 C6 C5 -0.4(3) . . . . ? O1 C1 C6 C7 -0.2(3) . . . . ? C2 C1 C6 C7 179.93(15) . . . . ? C5 C6 C7 C15 -61.3(4) . . . . ? C1 C6 C7 C15 118.4(3) . . . . ? C5 C6 C7 C12 118.4(3) . . . . ? C1 C6 C7 C12 -61.9(3) . . . . ? C5 C6 C7 C14 -0.9(3) . . . . ? C1 C6 C7 C14 178.7(2) . . . . ? C5 C6 C7 C13 62.6(3) . . . . ? C1 C6 C7 C13 -117.8(3) . . . . ? C5 C6 C7 C11 178.5(3) . . . . ? C1 C6 C7 C11 -1.9(3) . . . . ? C5 C6 C7 C10 -118.6(3) . . . . ? C1 C6 C7 C10 61.1(3) . . . . ? C1 C2 C8 C21 -61.2(3) . . . . ? C3 C2 C8 C21 118.6(3) . . . . ? C1 C2 C8 C18 118.3(3) . . . . ? C3 C2 C8 C18 -61.9(3) . . . . ? C1 C2 C8 C19 61.6(3) . . . . ? C3 C2 C8 C19 -118.6(3) . . . . ? C1 C2 C8 C16 -117.6(3) . . . . ? C3 C2 C8 C16 62.2(3) . . . . ? C1 C2 C8 C20 -0.9(3) . . . . ? C3 C2 C8 C20 178.8(3) . . . . ? C1 C2 C8 C17 179.4(2) . . . . ? C3 C2 C8 C17 -0.8(3) . . . . ? C3 C4 C9 C25 59.4(4) . . . . ? C5 C4 C9 C25 -120.0(3) . . . . ? C3 C4 C9 C26 3.1(3) . . . . ? C5 C4 C9 C26 -176.3(3) . . . . ? C3 C4 C9 C23 -176.9(3) . . . . ? C5 C4 C9 C23 3.7(4) . . . . ? C3 C4 C9 C22 -121.0(3) . . . . ? C5 C4 C9 C22 59.6(3) . . . . ? C3 C4 C9 C27 -61.3(3) . . . . ? C5 C4 C9 C27 119.3(3) . . . . ? C3 C4 C9 C24 119.5(3) . . . . ? C5 C4 C9 C24 -59.9(3) . . . . ? _diffrn_measured_fraction_theta_max 0.931 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.145 _refine_diff_density_min -0.158 _refine_diff_density_rms 0.041