# Electronic Supplementary Material (ESI) for Chemical Science # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full 'Chemical Science' _journal_coden_Cambridge 1475 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Dr Huw M L Davies' _publ_contact_author_email hmdavie@emory.edu _publ_section_title ; Asymmetric Synthesis of Highly Functionalized Cyclopentanes by a Rhodium- and Scandium-Catalyzed Five-Step Domino Sequence ; loop_ _publ_author_name B.Parr 'Zjanjie Li' H.M.L.Davies # Attachment '- compound 7a.cif' data_bp_4_083d _database_code_depnum_ccdc_archive 'CCDC 827543' #TrackingRef '- compound 7a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C17 H22 O3' _chemical_formula_sum 'C17 H22 O3' _chemical_formula_weight 274.35 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 12.7496(10) _cell_length_b 10.6190(12) _cell_length_c 22.4445(18) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3038.7(5) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 1222 _cell_measurement_theta_min 3.94 _cell_measurement_theta_max 55.36 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.199 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1184 _exptl_absorpt_coefficient_mu 0.646 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9150 _exptl_absorpt_correction_T_max 0.9721 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15922 _diffrn_reflns_av_R_equivalents 0.0829 _diffrn_reflns_av_sigmaI/netI 0.0529 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 3.94 _diffrn_reflns_theta_max 69.41 _reflns_number_total 2779 _reflns_number_gt 1615 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1300P)^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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0009(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2779 _refine_ls_number_parameters 190 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1217 _refine_ls_R_factor_gt 0.0761 _refine_ls_wR_factor_ref 0.2347 _refine_ls_wR_factor_gt 0.1951 _refine_ls_goodness_of_fit_ref 1.066 _refine_ls_restrained_S_all 1.066 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.2628(3) 0.2173(3) 0.27674(15) 0.0561(9) Uani 1 1 d . . . H1A H 0.3300 0.1735 0.2842 0.067 Uiso 1 1 calc R . . H1B H 0.2771 0.2941 0.2531 0.067 Uiso 1 1 calc R . . C2 C 0.2095(3) 0.2524(3) 0.33653(14) 0.0493(9) Uani 1 1 d . . . C3 C 0.1169(3) 0.1559(3) 0.34160(14) 0.0466(8) Uani 1 1 d . . . H3A H 0.1492 0.0735 0.3531 0.056 Uiso 1 1 calc R . . C4 C 0.0817(3) 0.1418(3) 0.27665(14) 0.0465(8) Uani 1 1 d . . . H4A H 0.0460 0.2212 0.2639 0.056 Uiso 1 1 calc R . . C5 C 0.1856(3) 0.1294(3) 0.24274(15) 0.0493(9) Uani 1 1 d . . . H5A H 0.2110 0.0410 0.2479 0.059 Uiso 1 1 calc R . . C6 C 0.1793(3) 0.1553(3) 0.17653(15) 0.0488(8) Uani 1 1 d . . . C7 C 0.2183(3) 0.0697(3) 0.13516(16) 0.0574(10) Uani 1 1 d . . . H7A H 0.2480 -0.0073 0.1487 0.069 Uiso 1 1 calc R . . C8 C 0.2146(3) 0.0947(4) 0.07459(17) 0.0650(11) Uani 1 1 d . . . H8A H 0.2418 0.0348 0.0472 0.078 Uiso 1 1 calc R . . C9 C 0.1725(3) 0.2047(4) 0.05373(17) 0.0648(11) Uani 1 1 d . . . H9A H 0.1705 0.2215 0.0122 0.078 Uiso 1 1 calc R . . C10 C 0.1326(3) 0.2910(3) 0.09410(16) 0.0619(10) Uani 1 1 d . . . H10A H 0.1029 0.3676 0.0802 0.074 Uiso 1 1 calc R . . C11 C 0.1361(3) 0.2662(3) 0.15458(15) 0.0564(10) Uani 1 1 d . . . H11A H 0.1083 0.3262 0.1817 0.068 Uiso 1 1 calc R . . C12 C 0.0071(3) 0.0308(3) 0.26655(16) 0.0580(10) Uani 1 1 d . . . H12A H -0.0130 0.0275 0.2244 0.087 Uiso 1 1 calc R . . H12B H -0.0558 0.0418 0.2911 0.087 Uiso 1 1 calc R . . H12C H 0.0423 -0.0478 0.2776 0.087 Uiso 1 1 calc R . . C13 C 0.2834(3) 0.2453(3) 0.38914(15) 0.0521(9) Uani 1 1 d . . . C14 C 0.3921(4) 0.1142(4) 0.44725(19) 0.0780(13) Uani 1 1 d . . . H14A H 0.4144 0.0260 0.4495 0.117 Uiso 1 1 calc R . . H14B H 0.3569 0.1379 0.4844 0.117 Uiso 1 1 calc R . . H14C H 0.4536 0.1682 0.4413 0.117 Uiso 1 1 calc R . . C15 C 0.0343(3) 0.1831(3) 0.38738(14) 0.0509(9) Uani 1 1 d . . . C16 C 0.0295(4) 0.1167(4) 0.43748(18) 0.0618(10) Uani 1 1 d . . . C17 C -0.0467(3) 0.2845(3) 0.37476(17) 0.0616(10) Uani 1 1 d . . . H17A H -0.0954 0.2905 0.4084 0.092 Uiso 1 1 calc R . . H17B H -0.0858 0.2628 0.3386 0.092 Uiso 1 1 calc R . . H17C H -0.0113 0.3655 0.3691 0.092 Uiso 1 1 calc R . . H16A H -0.026(3) 0.129(3) 0.4678(16) 0.060(11) Uiso 1 1 d . . . H16B H 0.074(3) 0.050(4) 0.4454(16) 0.067(11) Uiso 1 1 d . . . O1 O 0.1691(2) 0.3769(2) 0.33299(11) 0.0643(8) Uani 1 1 d . . . H1C H 0.2190 0.4282 0.3302 0.096 Uiso 1 1 calc R . . O2 O 0.3057(2) 0.3350(2) 0.41915(11) 0.0668(8) Uani 1 1 d . . . O3 O 0.3207(2) 0.1298(2) 0.39802(12) 0.0622(7) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.058(2) 0.0604(19) 0.0499(19) 0.0001(15) -0.0004(17) -0.0071(17) C2 0.056(2) 0.0374(15) 0.0542(19) 0.0016(13) -0.0012(16) -0.0073(14) C3 0.054(2) 0.0365(14) 0.0490(18) 0.0012(12) 0.0023(15) -0.0015(13) C4 0.055(2) 0.0372(15) 0.0477(17) -0.0002(13) -0.0009(15) -0.0002(13) C5 0.060(2) 0.0360(15) 0.0517(18) -0.0019(13) 0.0024(16) 0.0012(14) C6 0.057(2) 0.0372(15) 0.0520(18) -0.0051(13) 0.0016(16) -0.0043(13) C7 0.064(3) 0.0481(18) 0.060(2) -0.0072(16) 0.0001(18) 0.0011(16) C8 0.072(3) 0.067(2) 0.056(2) -0.0171(18) 0.004(2) -0.0051(19) C9 0.064(3) 0.080(3) 0.051(2) -0.0055(18) 0.0020(18) -0.014(2) C10 0.069(3) 0.0557(19) 0.061(2) 0.0071(17) -0.0028(19) -0.0031(18) C11 0.073(3) 0.0418(16) 0.054(2) -0.0028(14) 0.0044(18) -0.0002(16) C12 0.062(3) 0.0441(17) 0.067(2) -0.0059(15) -0.0034(19) -0.0053(16) C13 0.063(2) 0.0405(16) 0.0534(19) -0.0003(14) 0.0059(16) -0.0090(15) C14 0.076(3) 0.080(3) 0.078(3) 0.018(2) -0.027(2) -0.011(2) C15 0.060(2) 0.0390(15) 0.0537(19) -0.0010(14) 0.0005(16) -0.0038(14) C16 0.072(3) 0.056(2) 0.057(2) 0.0061(18) 0.010(2) 0.0013(19) C17 0.062(3) 0.0549(19) 0.068(2) 0.0016(17) 0.010(2) 0.0052(17) O1 0.0695(18) 0.0352(11) 0.0882(19) 0.0077(11) -0.0014(14) -0.0040(11) O2 0.087(2) 0.0541(14) 0.0588(15) -0.0088(11) -0.0049(14) -0.0127(13) O3 0.0692(19) 0.0493(13) 0.0682(16) 0.0022(11) -0.0172(13) -0.0007(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 C1 C2 1.550(5) . ? C1 C5 1.556(5) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 O1 1.421(4) . ? C2 C13 1.513(5) . ? C2 C3 1.568(4) . ? C3 C15 1.499(5) . ? C3 C4 1.533(4) . ? C3 H3A 1.0000 . ? C4 C12 1.531(4) . ? C4 C5 1.534(5) . ? C4 H4A 1.0000 . ? C5 C6 1.513(5) . ? C5 H5A 1.0000 . ? C6 C11 1.390(5) . ? C6 C7 1.392(5) . ? C7 C8 1.386(5) . ? C7 H7A 0.9500 . ? C8 C9 1.368(6) . ? C8 H8A 0.9500 . ? C9 C10 1.386(5) . ? C9 H9A 0.9500 . ? C10 C11 1.384(5) . ? C10 H10A 0.9500 . ? C11 H11A 0.9500 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 O2 1.201(4) . ? C13 O3 1.330(4) . ? C14 O3 1.442(5) . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 C16 1.328(5) . ? C15 C17 1.519(5) . ? C16 H16A 0.99(4) . ? C16 H16B 0.93(4) . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? O1 H1C 0.8400 . ? 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 C5 106.9(3) . . ? C2 C1 H1A 110.3 . . ? C5 C1 H1A 110.3 . . ? C2 C1 H1B 110.3 . . ? C5 C1 H1B 110.3 . . ? H1A C1 H1B 108.6 . . ? O1 C2 C13 108.4(3) . . ? O1 C2 C1 109.5(3) . . ? C13 C2 C1 113.0(3) . . ? O1 C2 C3 109.9(3) . . ? C13 C2 C3 112.3(3) . . ? C1 C2 C3 103.6(2) . . ? C15 C3 C4 117.7(3) . . ? C15 C3 C2 116.9(3) . . ? C4 C3 C2 102.4(2) . . ? C15 C3 H3A 106.3 . . ? C4 C3 H3A 106.3 . . ? C2 C3 H3A 106.3 . . ? C12 C4 C3 113.4(3) . . ? C12 C4 C5 113.4(3) . . ? C3 C4 C5 103.2(3) . . ? C12 C4 H4A 108.9 . . ? C3 C4 H4A 108.9 . . ? C5 C4 H4A 108.9 . . ? C6 C5 C4 115.2(3) . . ? C6 C5 C1 114.0(3) . . ? C4 C5 C1 104.6(3) . . ? C6 C5 H5A 107.6 . . ? C4 C5 H5A 107.6 . . ? C1 C5 H5A 107.6 . . ? C11 C6 C7 117.3(3) . . ? C11 C6 C5 121.5(3) . . ? C7 C6 C5 121.2(3) . . ? C8 C7 C6 121.1(3) . . ? C8 C7 H7A 119.4 . . ? C6 C7 H7A 119.4 . . ? C9 C8 C7 120.9(3) . . ? C9 C8 H8A 119.6 . . ? C7 C8 H8A 119.6 . . ? C8 C9 C10 119.0(4) . . ? C8 C9 H9A 120.5 . . ? C10 C9 H9A 120.5 . . ? C11 C10 C9 120.2(4) . . ? C11 C10 H10A 119.9 . . ? C9 C10 H10A 119.9 . . ? C10 C11 C6 121.5(3) . . ? C10 C11 H11A 119.3 . . ? C6 C11 H11A 119.3 . . ? C4 C12 H12A 109.5 . . ? C4 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C4 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? O2 C13 O3 124.2(3) . . ? O2 C13 C2 123.1(3) . . ? O3 C13 C2 112.7(3) . . ? O3 C14 H14A 109.5 . . ? O3 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? O3 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C16 C15 C3 120.7(3) . . ? C16 C15 C17 120.2(4) . . ? C3 C15 C17 119.1(3) . . ? C15 C16 H16A 123(2) . . ? C15 C16 H16B 123(2) . . ? H16A C16 H16B 114(3) . . ? C15 C17 H17A 109.5 . . ? C15 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C15 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C2 O1 H1C 109.5 . . ? C13 O3 C14 116.5(3) . . ? 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 C5 C1 C2 O1 -103.1(3) . . . . ? C5 C1 C2 C13 135.9(3) . . . . ? C5 C1 C2 C3 14.1(3) . . . . ? O1 C2 C3 C15 -49.1(4) . . . . ? C13 C2 C3 C15 71.7(4) . . . . ? C1 C2 C3 C15 -166.1(3) . . . . ? O1 C2 C3 C4 81.1(3) . . . . ? C13 C2 C3 C4 -158.1(3) . . . . ? C1 C2 C3 C4 -35.8(3) . . . . ? C15 C3 C4 C12 -62.8(4) . . . . ? C2 C3 C4 C12 167.5(3) . . . . ? C15 C3 C4 C5 174.1(2) . . . . ? C2 C3 C4 C5 44.4(3) . . . . ? C12 C4 C5 C6 75.5(3) . . . . ? C3 C4 C5 C6 -161.4(2) . . . . ? C12 C4 C5 C1 -158.6(3) . . . . ? C3 C4 C5 C1 -35.5(3) . . . . ? C2 C1 C5 C6 139.5(3) . . . . ? C2 C1 C5 C4 12.9(3) . . . . ? C4 C5 C6 C11 53.2(4) . . . . ? C1 C5 C6 C11 -67.6(5) . . . . ? C4 C5 C6 C7 -127.9(3) . . . . ? C1 C5 C6 C7 111.2(4) . . . . ? C11 C6 C7 C8 0.4(6) . . . . ? C5 C6 C7 C8 -178.5(4) . . . . ? C6 C7 C8 C9 0.0(6) . . . . ? C7 C8 C9 C10 -0.3(6) . . . . ? C8 C9 C10 C11 0.2(6) . . . . ? C9 C10 C11 C6 0.2(6) . . . . ? C7 C6 C11 C10 -0.5(6) . . . . ? C5 C6 C11 C10 178.4(3) . . . . ? O1 C2 C13 O2 -3.9(5) . . . . ? C1 C2 C13 O2 117.7(4) . . . . ? C3 C2 C13 O2 -125.5(4) . . . . ? O1 C2 C13 O3 176.5(3) . . . . ? C1 C2 C13 O3 -61.9(4) . . . . ? C3 C2 C13 O3 54.9(4) . . . . ? C4 C3 C15 C16 131.3(4) . . . . ? C2 C3 C15 C16 -106.0(4) . . . . ? C4 C3 C15 C17 -46.4(4) . . . . ? C2 C3 C15 C17 76.2(4) . . . . ? O2 C13 O3 C14 0.2(6) . . . . ? C2 C13 O3 C14 179.9(3) . . . . ? _diffrn_measured_fraction_theta_max 0.974 _diffrn_reflns_theta_full 69.41 _diffrn_measured_fraction_theta_full 0.974 _refine_diff_density_max 0.285 _refine_diff_density_min -0.395 _refine_diff_density_rms 0.078 # Attachment '- compound 9c.cif' data_bp_8_037b _database_code_depnum_ccdc_archive 'CCDC 827544' #TrackingRef '- compound 9c.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H21 Br O3' _chemical_formula_weight 353.25 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) _chemical_absolute_configuration ad loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 5.8343(3) _cell_length_b 7.4644(4) _cell_length_c 37.7001(18) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1641.82(14) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 9939 _cell_measurement_theta_min 2.34 _cell_measurement_theta_max 68.92 _exptl_crystal_description irreg _exptl_crystal_colour colorless _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.429 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 728 _exptl_absorpt_coefficient_mu 3.473 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3678 _exptl_absorpt_correction_T_max 0.6065 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13100 _diffrn_reflns_av_R_equivalents 0.0216 _diffrn_reflns_av_sigmaI/netI 0.0175 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -41 _diffrn_reflns_limit_l_max 45 _diffrn_reflns_theta_min 2.34 _diffrn_reflns_theta_max 69.24 _reflns_number_total 2837 _reflns_number_gt 2816 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0391P)^2^+0.6504P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.024(16) _refine_ls_number_reflns 2837 _refine_ls_number_parameters 190 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0245 _refine_ls_R_factor_gt 0.0243 _refine_ls_wR_factor_ref 0.0654 _refine_ls_wR_factor_gt 0.0653 _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_restrained_S_all 1.028 _refine_ls_shift/su_max 0.004 _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 0.33767(5) 0.03062(4) 0.815225(6) 0.04457(10) Uani 1 1 d . . . C1 C 0.1529(5) -0.1691(3) 0.63753(6) 0.0329(5) Uani 1 1 d . . . H1A H 0.2371 -0.2482 0.6541 0.039 Uiso 1 1 calc R . . H1B H 0.0053 -0.2268 0.6314 0.039 Uiso 1 1 calc R . . C2 C 0.2954(4) -0.1357(3) 0.60385(6) 0.0287(5) Uani 1 1 d . . . C3 C 0.2374(4) 0.0629(3) 0.59516(6) 0.0266(5) Uani 1 1 d . . . H3A H 0.0728 0.0655 0.5878 0.032 Uiso 1 1 calc R . . C4 C 0.2487(4) 0.1498(3) 0.63197(6) 0.0274(5) Uani 1 1 d . . . H4A H 0.4116 0.1495 0.6402 0.033 Uiso 1 1 calc R . . C5 C 0.1105(4) 0.0171(3) 0.65482(6) 0.0283(5) Uani 1 1 d . . . H5A H -0.0557 0.0466 0.6520 0.034 Uiso 1 1 calc R . . C6 C 0.1677(4) 0.0245(3) 0.69405(5) 0.0271(4) Uani 1 1 d . . . C7 C 0.3774(4) -0.0379(3) 0.70650(6) 0.0313(5) Uani 1 1 d . . . H7A H 0.4873 -0.0824 0.6901 0.038 Uiso 1 1 calc R . . C8 C 0.4286(4) -0.0362(3) 0.74253(6) 0.0320(5) Uani 1 1 d . . . H8A H 0.5714 -0.0803 0.7509 0.038 Uiso 1 1 calc R . . C9 C 0.2681(4) 0.0308(3) 0.76579(5) 0.0297(5) Uani 1 1 d . . . C10 C 0.0618(4) 0.0981(3) 0.75439(6) 0.0328(5) Uani 1 1 d . . . H10A H -0.0450 0.1464 0.7708 0.039 Uiso 1 1 calc R . . C11 C 0.0121(4) 0.0942(3) 0.71839(6) 0.0304(5) Uani 1 1 d . . . H11A H -0.1304 0.1398 0.7102 0.037 Uiso 1 1 calc R . . C12 C 0.1588(5) 0.3405(3) 0.63318(6) 0.0372(5) Uani 1 1 d . . . H12A H 0.2542 0.4171 0.6181 0.056 Uiso 1 1 calc R . . H12B H 0.1638 0.3846 0.6577 0.056 Uiso 1 1 calc R . . H12C H 0.0003 0.3429 0.6246 0.056 Uiso 1 1 calc R . . C13 C 0.3721(4) 0.1465(3) 0.56534(6) 0.0332(5) Uani 1 1 d . . . C14 C 0.2814(5) 0.1564(4) 0.53326(7) 0.0457(7) Uani 1 1 d . . . H14A H 0.1357 0.0930 0.5276 0.069 Uiso 1 1 d R . . H14B H 0.3517 0.2084 0.5140 0.069 Uiso 1 1 d R . . C15 C 0.6048(5) 0.2194(5) 0.57349(8) 0.0537(8) Uani 1 1 d . . . H15A H 0.6726 0.2692 0.5518 0.081 Uiso 1 1 calc R . . H15B H 0.7026 0.1230 0.5825 0.081 Uiso 1 1 calc R . . H15C H 0.5918 0.3139 0.5914 0.081 Uiso 1 1 calc R . . C16 C 0.2416(4) -0.2559(3) 0.57257(6) 0.0298(5) Uani 1 1 d . . . C17 C -0.0405(5) -0.3703(4) 0.53431(7) 0.0466(7) Uani 1 1 d . . . H17A H -0.2068 -0.3672 0.5307 0.070 Uiso 1 1 calc R . . H17B H 0.0088 -0.4943 0.5382 0.070 Uiso 1 1 calc R . . H17C H 0.0367 -0.3219 0.5133 0.070 Uiso 1 1 calc R . . O1 O 0.5321(3) -0.1541(2) 0.61206(5) 0.0385(4) Uani 1 1 d . . . H1C H 0.5610 -0.2618 0.6167 0.058 Uiso 1 1 calc R . . O2 O 0.0185(3) -0.2629(2) 0.56506(4) 0.0360(4) Uani 1 1 d . . . O3 O 0.3871(3) -0.3302(2) 0.55558(5) 0.0424(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.05029(16) 0.05768(16) 0.02576(13) 0.00007(11) -0.00298(11) -0.01601(13) C1 0.0428(13) 0.0281(10) 0.0278(11) 0.0009(9) -0.0009(11) -0.0066(11) C2 0.0296(12) 0.0285(11) 0.0281(11) 0.0012(9) -0.0051(10) 0.0033(9) C3 0.0238(10) 0.0300(11) 0.0262(10) 0.0025(9) 0.0003(8) 0.0038(8) C4 0.0263(10) 0.0280(11) 0.0280(11) 0.0003(9) -0.0008(9) 0.0002(9) C5 0.0281(11) 0.0303(10) 0.0266(10) 0.0008(9) -0.0010(8) -0.0022(9) C6 0.0292(10) 0.0249(9) 0.0273(10) -0.0007(8) 0.0032(9) -0.0032(10) C7 0.0298(12) 0.0347(10) 0.0295(11) -0.0033(9) 0.0036(9) 0.0044(11) C8 0.0290(11) 0.0345(10) 0.0324(11) 0.0016(10) -0.0022(9) -0.0023(10) C9 0.0400(12) 0.0273(10) 0.0217(10) -0.0005(9) -0.0007(9) -0.0091(10) C10 0.0327(12) 0.0338(11) 0.0320(12) -0.0041(10) 0.0097(10) -0.0010(10) C11 0.0274(11) 0.0300(10) 0.0339(12) 0.0010(10) 0.0026(9) 0.0020(9) C12 0.0464(14) 0.0286(10) 0.0367(12) -0.0013(9) 0.0009(12) 0.0028(11) C13 0.0394(13) 0.0280(11) 0.0321(12) 0.0025(9) 0.0073(11) 0.0053(10) C14 0.0605(18) 0.0468(15) 0.0298(12) 0.0078(11) 0.0027(12) -0.0014(13) C15 0.0361(15) 0.0650(18) 0.0602(18) 0.0151(16) 0.0083(13) -0.0076(13) C16 0.0350(12) 0.0259(10) 0.0286(11) 0.0025(9) 0.0020(10) 0.0017(9) C17 0.0451(15) 0.0563(17) 0.0383(13) -0.0122(13) -0.0055(12) -0.0101(13) O1 0.0370(10) 0.0362(9) 0.0423(10) -0.0014(7) -0.0112(8) 0.0103(8) O2 0.0340(9) 0.0424(9) 0.0316(8) -0.0098(8) -0.0037(7) 0.0004(8) O3 0.0364(10) 0.0472(10) 0.0436(10) -0.0129(9) 0.0042(8) 0.0036(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 C9 1.907(2) . ? C1 C2 1.538(3) . ? C1 C5 1.554(3) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 O1 1.422(3) . ? C2 C16 1.515(3) . ? C2 C3 1.556(3) . ? C3 C13 1.507(3) . ? C3 C4 1.533(3) . ? C3 H3A 1.0000 . ? C4 C12 1.517(3) . ? C4 C5 1.541(3) . ? C4 H4A 1.0000 . ? C5 C6 1.517(3) . ? C5 H5A 1.0000 . ? C6 C7 1.390(3) . ? C6 C11 1.392(3) . ? C7 C8 1.391(3) . ? C7 H7A 0.9500 . ? C8 C9 1.377(3) . ? C8 H8A 0.9500 . ? C9 C10 1.374(3) . ? C10 C11 1.388(3) . ? C10 H10A 0.9500 . ? C11 H11A 0.9500 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 C14 1.322(4) . ? C13 C15 1.495(4) . ? C14 H14A 0.9962 . ? C14 H14B 0.9202 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 O3 1.199(3) . ? C16 O2 1.333(3) . ? C17 O2 1.451(3) . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? O1 H1C 0.8400 . ? 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 C5 106.72(17) . . ? C2 C1 H1A 110.4 . . ? C5 C1 H1A 110.4 . . ? C2 C1 H1B 110.4 . . ? C5 C1 H1B 110.4 . . ? H1A C1 H1B 108.6 . . ? O1 C2 C16 108.28(19) . . ? O1 C2 C1 109.24(19) . . ? C16 C2 C1 115.8(2) . . ? O1 C2 C3 110.42(18) . . ? C16 C2 C3 110.84(18) . . ? C1 C2 C3 102.15(18) . . ? C13 C3 C4 118.54(19) . . ? C13 C3 C2 116.00(19) . . ? C4 C3 C2 101.74(17) . . ? C13 C3 H3A 106.6 . . ? C4 C3 H3A 106.6 . . ? C2 C3 H3A 106.6 . . ? C12 C4 C3 114.16(19) . . ? C12 C4 C5 113.9(2) . . ? C3 C4 C5 102.22(17) . . ? C12 C4 H4A 108.8 . . ? C3 C4 H4A 108.8 . . ? C5 C4 H4A 108.8 . . ? C6 C5 C4 113.97(18) . . ? C6 C5 C1 113.99(18) . . ? C4 C5 C1 104.89(17) . . ? C6 C5 H5A 107.9 . . ? C4 C5 H5A 107.9 . . ? C1 C5 H5A 107.9 . . ? C7 C6 C11 118.4(2) . . ? C7 C6 C5 120.70(19) . . ? C11 C6 C5 120.9(2) . . ? C6 C7 C8 121.0(2) . . ? C6 C7 H7A 119.5 . . ? C8 C7 H7A 119.5 . . ? C9 C8 C7 118.6(2) . . ? C9 C8 H8A 120.7 . . ? C7 C8 H8A 120.7 . . ? C10 C9 C8 122.0(2) . . ? C10 C9 Br1 119.50(18) . . ? C8 C9 Br1 118.52(18) . . ? C9 C10 C11 118.8(2) . . ? C9 C10 H10A 120.6 . . ? C11 C10 H10A 120.6 . . ? C10 C11 C6 121.1(2) . . ? C10 C11 H11A 119.5 . . ? C6 C11 H11A 119.5 . . ? C4 C12 H12A 109.5 . . ? C4 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C4 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C14 C13 C15 122.1(2) . . ? C14 C13 C3 119.8(2) . . ? C15 C13 C3 118.1(2) . . ? C13 C14 H14A 120.8 . . ? C13 C14 H14B 124.6 . . ? H14A C14 H14B 114.3 . . ? C13 C15 H15A 109.5 . . ? C13 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C13 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? O3 C16 O2 124.0(2) . . ? O3 C16 C2 122.9(2) . . ? O2 C16 C2 113.0(2) . . ? O2 C17 H17A 109.5 . . ? O2 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? O2 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C2 O1 H1C 109.5 . . ? C16 O2 C17 115.0(2) . . ? 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 C5 C1 C2 O1 93.5(2) . . . . ? C5 C1 C2 C16 -144.02(19) . . . . ? C5 C1 C2 C3 -23.5(2) . . . . ? O1 C2 C3 C13 57.2(3) . . . . ? C16 C2 C3 C13 -62.8(2) . . . . ? C1 C2 C3 C13 173.3(2) . . . . ? O1 C2 C3 C4 -73.0(2) . . . . ? C16 C2 C3 C4 167.05(19) . . . . ? C1 C2 C3 C4 43.1(2) . . . . ? C13 C3 C4 C12 61.6(3) . . . . ? C2 C3 C4 C12 -169.9(2) . . . . ? C13 C3 C4 C5 -174.91(19) . . . . ? C2 C3 C4 C5 -46.4(2) . . . . ? C12 C4 C5 C6 -79.5(2) . . . . ? C3 C4 C5 C6 156.86(18) . . . . ? C12 C4 C5 C1 155.2(2) . . . . ? C3 C4 C5 C1 31.5(2) . . . . ? C2 C1 C5 C6 -130.0(2) . . . . ? C2 C1 C5 C4 -4.7(2) . . . . ? C4 C5 C6 C7 -70.4(3) . . . . ? C1 C5 C6 C7 50.0(3) . . . . ? C4 C5 C6 C11 109.5(2) . . . . ? C1 C5 C6 C11 -130.2(2) . . . . ? C11 C6 C7 C8 2.0(3) . . . . ? C5 C6 C7 C8 -178.2(2) . . . . ? C6 C7 C8 C9 -0.8(4) . . . . ? C7 C8 C9 C10 -1.0(4) . . . . ? C7 C8 C9 Br1 179.35(18) . . . . ? C8 C9 C10 C11 1.6(4) . . . . ? Br1 C9 C10 C11 -178.81(19) . . . . ? C9 C10 C11 C6 -0.3(3) . . . . ? C7 C6 C11 C10 -1.4(3) . . . . ? C5 C6 C11 C10 178.7(2) . . . . ? C4 C3 C13 C14 -140.0(2) . . . . ? C2 C3 C13 C14 98.4(3) . . . . ? C4 C3 C13 C15 38.8(3) . . . . ? C2 C3 C13 C15 -82.7(3) . . . . ? O1 C2 C16 O3 -9.6(3) . . . . ? C1 C2 C16 O3 -132.7(3) . . . . ? C3 C2 C16 O3 111.6(3) . . . . ? O1 C2 C16 O2 173.4(2) . . . . ? C1 C2 C16 O2 50.4(3) . . . . ? C3 C2 C16 O2 -65.4(3) . . . . ? O3 C16 O2 C17 0.5(4) . . . . ? C2 C16 O2 C17 177.4(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1C Br1 0.84 3.05 3.6918(17) 134.5 3_646 _diffrn_measured_fraction_theta_max 0.972 _diffrn_reflns_theta_full 69.24 _diffrn_measured_fraction_theta_full 0.972 _refine_diff_density_max 0.289 _refine_diff_density_min -0.308 _refine_diff_density_rms 0.051 # Attachment '- compound 12.cif' data_123a _database_code_depnum_ccdc_archive 'CCDC 827545' #TrackingRef '- compound 12.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H24 O4' _chemical_formula_weight 304.37 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 12.1533(3) _cell_length_b 35.1495(7) _cell_length_c 12.2922(3) _cell_angle_alpha 90.00 _cell_angle_beta 110.6840(10) _cell_angle_gamma 90.00 _cell_volume 4912.5(2) _cell_formula_units_Z 12 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 9893 _cell_measurement_theta_min 3.77 _cell_measurement_theta_max 69.15 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.235 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1968 _exptl_absorpt_coefficient_mu 0.696 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7681 _exptl_absorpt_correction_T_max 0.9149 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 41157 _diffrn_reflns_av_R_equivalents 0.1191 _diffrn_reflns_av_sigmaI/netI 0.0651 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -37 _diffrn_reflns_limit_k_max 41 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.51 _diffrn_reflns_theta_max 67.32 _reflns_number_total 8401 _reflns_number_gt 6171 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1740P)^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 SHELXL _refine_ls_extinction_coef 0.00078(18) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 8401 _refine_ls_number_parameters 596 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0976 _refine_ls_R_factor_gt 0.0801 _refine_ls_wR_factor_ref 0.2637 _refine_ls_wR_factor_gt 0.2275 _refine_ls_goodness_of_fit_ref 1.132 _refine_ls_restrained_S_all 1.132 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.5739(3) 0.02391(7) 0.1776(3) 0.0378(7) Uani 1 1 d . . . H1A H 0.6408 0.0158 0.1549 0.045 Uiso 1 1 calc R . . H1B H 0.5003 0.0166 0.1142 0.045 Uiso 1 1 calc R . . C2 C 0.5803(2) 0.00345(7) 0.2887(2) 0.0350(6) Uani 1 1 d . . . H2A H 0.5082 0.0087 0.3061 0.042 Uiso 1 1 calc R . . H2B H 0.5854 -0.0243 0.2784 0.042 Uiso 1 1 calc R . . C3 C 0.6875(2) 0.01696(6) 0.3888(2) 0.0311(6) Uani 1 1 d . . . H3A H 0.7601 0.0087 0.3746 0.037 Uiso 1 1 calc R . . C4 C 0.6977(2) 0.00532(7) 0.5116(2) 0.0341(6) Uani 1 1 d . . . H4A H 0.6204 0.0105 0.5205 0.041 Uiso 1 1 calc R . . C5 C 0.7880(3) 0.03388(7) 0.5880(3) 0.0412(7) Uani 1 1 d . . . H5A H 0.8682 0.0230 0.6122 0.049 Uiso 1 1 calc R . . H5B H 0.7701 0.0399 0.6587 0.049 Uiso 1 1 calc R . . C6 C 0.7800(2) 0.07059(7) 0.5141(3) 0.0331(6) Uani 1 1 d . . . C7 C 0.6860(2) 0.06053(6) 0.3950(2) 0.0304(6) Uani 1 1 d . . . H7A H 0.6090 0.0670 0.4027 0.037 Uiso 1 1 calc R . . C8 C 0.6826(2) 0.07967(7) 0.2816(3) 0.0358(6) Uani 1 1 d . . . C9 C 0.6588(3) 0.12191(7) 0.2822(3) 0.0489(8) Uani 1 1 d . . . H9A H 0.5897 0.1261 0.3040 0.073 Uiso 1 1 calc R . . H9B H 0.6443 0.1324 0.2045 0.073 Uiso 1 1 calc R . . H9C H 0.7272 0.1346 0.3385 0.073 Uiso 1 1 calc R . . C10 C 0.7898(3) 0.07232(8) 0.2464(3) 0.0437(7) Uani 1 1 d . . . H10A H 0.7798 0.0857 0.1736 0.066 Uiso 1 1 calc R . . H10B H 0.7972 0.0450 0.2353 0.066 Uiso 1 1 calc R . . H10C H 0.8609 0.0816 0.3077 0.066 Uiso 1 1 calc R . . C11 C 0.7414(2) 0.10466(7) 0.5692(2) 0.0359(6) Uani 1 1 d . . . C12 C 0.5967(3) 0.12672(10) 0.6417(3) 0.0632(10) Uani 1 1 d . . . H12A H 0.5227 0.1183 0.6489 0.095 Uiso 1 1 calc R . . H12B H 0.5832 0.1501 0.5953 0.095 Uiso 1 1 calc R . . H12C H 0.6547 0.1316 0.7193 0.095 Uiso 1 1 calc R . . C13 C 0.7275(2) -0.03621(7) 0.5398(2) 0.0347(6) Uani 1 1 d . . . C14 C 0.6475(3) -0.06010(8) 0.5627(3) 0.0425(7) Uani 1 1 d . . . H14A H 0.5748 -0.0500 0.5622 0.051 Uiso 1 1 calc R . . C15 C 0.6714(3) -0.09838(8) 0.5862(3) 0.0479(8) Uani 1 1 d . . . H15A H 0.6157 -0.1141 0.6026 0.057 Uiso 1 1 calc R . . C16 C 0.7757(3) -0.11373(7) 0.5859(3) 0.0457(7) Uani 1 1 d . . . H16A H 0.7916 -0.1400 0.6011 0.055 Uiso 1 1 calc R . . C17 C 0.8570(3) -0.09050(7) 0.5633(3) 0.0427(7) Uani 1 1 d . . . H17A H 0.9294 -0.1008 0.5634 0.051 Uiso 1 1 calc R . . C18 C 0.8323(2) -0.05188(7) 0.5402(3) 0.0385(7) Uani 1 1 d . . . H18A H 0.8884 -0.0361 0.5245 0.046 Uiso 1 1 calc R . . O1 O 0.57713(17) 0.06460(5) 0.19160(17) 0.0367(5) Uani 1 1 d . . . O2 O 0.88927(17) 0.07863(5) 0.50224(18) 0.0420(5) Uani 1 1 d . . . H2C H 0.9378 0.0856 0.5667 0.063 Uiso 1 1 calc R . . O3 O 0.7947(2) 0.13392(5) 0.5977(2) 0.0594(7) Uani 1 1 d . . . O4 O 0.64051(19) 0.09729(6) 0.5850(2) 0.0497(6) Uani 1 1 d . . . C1B C 0.0845(3) 0.14123(7) -0.3083(3) 0.0425(7) Uani 1 1 d . . . H1BA H 0.0174 0.1514 -0.3741 0.051 Uiso 1 1 calc R . . H1BB H 0.1552 0.1421 -0.3306 0.051 Uiso 1 1 calc R . . C2B C 0.1044(3) 0.16612(7) -0.2016(3) 0.0391(7) Uani 1 1 d . . . H2BA H 0.0308 0.1680 -0.1845 0.047 Uiso 1 1 calc R . . H2BB H 0.1273 0.1921 -0.2165 0.047 Uiso 1 1 calc R . . C3B C 0.2015(2) 0.14869(6) -0.0979(2) 0.0322(6) Uani 1 1 d . . . H3BA H 0.2766 0.1492 -0.1140 0.039 Uiso 1 1 calc R . . C4B C 0.2237(2) 0.16667(6) 0.0217(2) 0.0349(7) Uani 1 1 d . . . H4BA H 0.1471 0.1762 0.0239 0.042 Uiso 1 1 calc R . . C5B C 0.2651(3) 0.13302(7) 0.1091(3) 0.0382(7) Uani 1 1 d . . . H5BA H 0.3461 0.1376 0.1639 0.046 Uiso 1 1 calc R . . H5BB H 0.2125 0.1302 0.1543 0.046 Uiso 1 1 calc R . . C6B C 0.2612(2) 0.09648(7) 0.0364(2) 0.0327(6) Uani 1 1 d . . . C7B C 0.1706(2) 0.10728(6) -0.0833(2) 0.0311(6) Uani 1 1 d . . . H7BA H 0.0924 0.1079 -0.0733 0.037 Uiso 1 1 calc R . . C8B C 0.1534(2) 0.08325(7) -0.1920(3) 0.0376(7) Uani 1 1 d . . . C9B C 0.1002(3) 0.04462(7) -0.1850(3) 0.0500(8) Uani 1 1 d . . . H9BA H 0.0298 0.0480 -0.1645 0.075 Uiso 1 1 calc R . . H9BB H 0.1577 0.0291 -0.1255 0.075 Uiso 1 1 calc R . . H9BC H 0.0786 0.0318 -0.2605 0.075 Uiso 1 1 calc R . . C10B C 0.2626(3) 0.07819(9) -0.2250(3) 0.0508(8) Uani 1 1 d . . . H10D H 0.2430 0.0623 -0.2947 0.076 Uiso 1 1 calc R . . H10E H 0.3249 0.0659 -0.1607 0.076 Uiso 1 1 calc R . . H10F H 0.2898 0.1031 -0.2406 0.076 Uiso 1 1 calc R . . C11B C 0.2250(2) 0.06183(7) 0.0910(3) 0.0346(6) Uani 1 1 d . . . C12B C 0.0713(3) 0.03596(8) 0.1449(3) 0.0521(9) Uani 1 1 d . . . H12D H -0.0081 0.0424 0.1422 0.078 Uiso 1 1 calc R . . H12E H 0.1229 0.0323 0.2260 0.078 Uiso 1 1 calc R . . H12F H 0.0685 0.0124 0.1013 0.078 Uiso 1 1 calc R . . C13B C 0.3086(3) 0.19967(6) 0.0459(3) 0.0346(6) Uani 1 1 d . . . C14B C 0.2748(3) 0.23629(7) 0.0632(3) 0.0458(8) Uani 1 1 d . . . H14B H 0.1979 0.2407 0.0638 0.055 Uiso 1 1 calc R . . C15B C 0.3532(3) 0.26684(8) 0.0798(3) 0.0550(9) Uani 1 1 d . . . H15B H 0.3300 0.2918 0.0925 0.066 Uiso 1 1 calc R . . C16B C 0.4641(3) 0.26045(8) 0.0777(3) 0.0500(8) Uani 1 1 d . . . H16B H 0.5167 0.2812 0.0871 0.060 Uiso 1 1 calc R . . C17B C 0.4995(3) 0.22422(8) 0.0621(3) 0.0446(7) Uani 1 1 d . . . H17B H 0.5767 0.2200 0.0621 0.054 Uiso 1 1 calc R . . C18B C 0.4226(2) 0.19429(7) 0.0467(3) 0.0375(7) Uani 1 1 d . . . H18B H 0.4476 0.1694 0.0363 0.045 Uiso 1 1 calc R . . O1B O 0.06077(18) 0.10247(5) -0.28723(18) 0.0414(5) Uani 1 1 d . . . O2B O 0.37039(16) 0.08991(5) 0.02348(18) 0.0414(5) Uani 1 1 d . . . H2BC H 0.4193 0.0823 0.0869 0.062 Uiso 1 1 calc R . . O3B O 0.28471(19) 0.03455(5) 0.1282(2) 0.0508(6) Uani 1 1 d . . . O4B O 0.11655(17) 0.06648(5) 0.09386(19) 0.0426(5) Uani 1 1 d . . . C1C C 0.9901(3) 0.19334(7) 0.3197(3) 0.0397(7) Uani 1 1 d . . . H1CA H 0.9178 0.1930 0.3394 0.048 Uiso 1 1 calc R . . H1CB H 1.0553 0.1832 0.3873 0.048 Uiso 1 1 calc R . . C2C C 0.9725(3) 0.16781(7) 0.2144(3) 0.0406(7) Uani 1 1 d . . . H2CA H 0.9475 0.1421 0.2292 0.049 Uiso 1 1 calc R . . H2CB H 1.0475 0.1653 0.2003 0.049 Uiso 1 1 calc R . . C3C C 0.8787(2) 0.18529(6) 0.1079(2) 0.0321(6) Uani 1 1 d . . . H3CA H 0.8015 0.1849 0.1199 0.039 Uiso 1 1 calc R . . C4C C 0.8628(2) 0.16738(6) -0.0102(2) 0.0357(7) Uani 1 1 d . . . H4CA H 0.9421 0.1593 -0.0092 0.043 Uiso 1 1 calc R . . C5C C 0.8194(3) 0.20055(7) -0.0992(3) 0.0399(7) Uani 1 1 d . . . H5CA H 0.7376 0.1959 -0.1520 0.048 Uiso 1 1 calc R . . H5CB H 0.8702 0.2029 -0.1465 0.048 Uiso 1 1 calc R . . C6C C 0.8257(2) 0.23750(7) -0.0268(2) 0.0323(6) Uani 1 1 d . . . C7C C 0.9116(2) 0.22660(6) 0.0946(2) 0.0317(6) Uani 1 1 d . . . H7CA H 0.9913 0.2257 0.0880 0.038 Uiso 1 1 calc R . . C8C C 0.9255(3) 0.25091(7) 0.2026(3) 0.0370(7) Uani 1 1 d . . . C9C C 0.9791(3) 0.28940(7) 0.1951(3) 0.0481(8) Uani 1 1 d . . . H9CA H 0.9861 0.3044 0.2644 0.072 Uiso 1 1 calc R . . H9CB H 0.9286 0.3029 0.1256 0.072 Uiso 1 1 calc R . . H9CC H 1.0573 0.2858 0.1904 0.072 Uiso 1 1 calc R . . C10C C 0.8156(3) 0.25623(9) 0.2336(3) 0.0480(8) Uani 1 1 d . . . H10G H 0.8342 0.2724 0.3026 0.072 Uiso 1 1 calc R . . H10H H 0.7881 0.2314 0.2497 0.072 Uiso 1 1 calc R . . H10I H 0.7539 0.2683 0.1683 0.072 Uiso 1 1 calc R . . C11C C 0.8656(3) 0.27102(7) -0.0832(3) 0.0353(6) Uani 1 1 d . . . C12C C 1.0229(3) 0.29512(9) -0.1345(3) 0.0606(10) Uani 1 1 d . . . H12G H 1.1040 0.2887 -0.1262 0.091 Uiso 1 1 calc R . . H12H H 1.0218 0.3198 -0.0977 0.091 Uiso 1 1 calc R . . H12I H 0.9745 0.2966 -0.2173 0.091 Uiso 1 1 calc R . . C13C C 0.7837(2) 0.13276(7) -0.0387(2) 0.0332(6) Uani 1 1 d . . . C14C C 0.8243(3) 0.09765(7) -0.0606(3) 0.0429(7) Uani 1 1 d . . . H14C H 0.9030 0.0952 -0.0583 0.052 Uiso 1 1 calc R . . C15C C 0.7505(3) 0.06588(8) -0.0861(3) 0.0539(9) Uani 1 1 d . . . H15C H 0.7786 0.0421 -0.1022 0.065 Uiso 1 1 calc R . . C16C C 0.6373(3) 0.06901(9) -0.0879(3) 0.0559(9) Uani 1 1 d . . . H16C H 0.5878 0.0472 -0.1035 0.067 Uiso 1 1 calc R . . C17C C 0.5949(3) 0.10386(9) -0.0669(3) 0.0484(8) Uani 1 1 d . . . H17C H 0.5163 0.1061 -0.0690 0.058 Uiso 1 1 calc R . . C18C C 0.6676(3) 0.13527(8) -0.0430(3) 0.0404(7) Uani 1 1 d . . . H18C H 0.6381 0.1591 -0.0292 0.048 Uiso 1 1 calc R . . O1C O 1.01615(17) 0.23175(5) 0.29840(18) 0.0381(5) Uani 1 1 d . . . O2C O 0.71513(17) 0.24586(6) -0.01879(19) 0.0441(5) Uani 1 1 d . . . H2CC H 0.6676 0.2520 -0.0846 0.066 Uiso 1 1 calc R . . O3C O 0.8063(2) 0.29761(5) -0.1279(2) 0.0545(6) Uani 1 1 d . . . O4C O 0.97634(18) 0.26606(5) -0.0790(2) 0.0460(6) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0459(16) 0.0259(13) 0.0461(17) -0.0047(11) 0.0217(14) 0.0022(11) C2 0.0382(15) 0.0251(12) 0.0468(17) -0.0045(11) 0.0211(14) -0.0022(10) C3 0.0374(14) 0.0220(11) 0.0427(16) -0.0016(11) 0.0252(13) 0.0011(10) C4 0.0392(15) 0.0266(12) 0.0454(17) 0.0002(11) 0.0259(14) 0.0026(10) C5 0.0593(19) 0.0251(13) 0.0450(17) 0.0004(12) 0.0257(16) 0.0012(12) C6 0.0384(15) 0.0253(12) 0.0410(16) -0.0016(11) 0.0207(13) -0.0017(10) C7 0.0368(14) 0.0222(11) 0.0392(16) -0.0030(10) 0.0219(13) 0.0001(10) C8 0.0412(16) 0.0252(12) 0.0474(17) 0.0008(11) 0.0234(14) -0.0023(10) C9 0.070(2) 0.0238(14) 0.055(2) 0.0026(12) 0.0242(18) -0.0005(13) C10 0.0451(17) 0.0477(16) 0.0468(18) 0.0045(13) 0.0269(15) -0.0041(13) C11 0.0430(16) 0.0282(13) 0.0398(16) -0.0018(11) 0.0186(14) -0.0013(11) C12 0.078(3) 0.063(2) 0.062(2) -0.0138(17) 0.040(2) 0.0201(18) C13 0.0488(16) 0.0230(12) 0.0402(16) -0.0006(11) 0.0257(14) 0.0000(11) C14 0.0454(17) 0.0369(14) 0.057(2) 0.0061(13) 0.0325(16) 0.0035(12) C15 0.0525(19) 0.0370(15) 0.061(2) 0.0097(14) 0.0280(17) -0.0066(13) C16 0.061(2) 0.0260(13) 0.0514(19) 0.0063(12) 0.0222(17) 0.0028(13) C17 0.0504(18) 0.0319(14) 0.0537(19) 0.0037(13) 0.0281(16) 0.0111(12) C18 0.0470(16) 0.0308(13) 0.0483(18) 0.0036(12) 0.0300(15) 0.0010(11) O1 0.0438(11) 0.0258(9) 0.0425(12) -0.0012(8) 0.0178(10) 0.0011(7) O2 0.0402(11) 0.0448(11) 0.0476(13) -0.0058(9) 0.0238(10) -0.0051(8) O3 0.0735(16) 0.0287(10) 0.0855(18) -0.0160(11) 0.0400(15) -0.0104(10) O4 0.0565(13) 0.0459(11) 0.0613(15) -0.0168(10) 0.0390(12) -0.0016(9) C1B 0.0501(18) 0.0297(14) 0.0504(19) 0.0043(12) 0.0211(15) -0.0078(12) C2B 0.0468(16) 0.0252(12) 0.0491(18) 0.0063(12) 0.0218(15) -0.0011(11) C3B 0.0376(15) 0.0217(12) 0.0448(17) -0.0001(11) 0.0238(13) -0.0041(10) C4B 0.0401(15) 0.0251(12) 0.0512(18) -0.0020(11) 0.0304(14) -0.0018(10) C5B 0.0533(18) 0.0275(13) 0.0425(17) -0.0005(12) 0.0274(15) -0.0075(11) C6B 0.0369(15) 0.0257(12) 0.0444(16) 0.0027(11) 0.0255(14) -0.0011(10) C7B 0.0349(14) 0.0207(11) 0.0452(17) 0.0007(11) 0.0232(13) -0.0025(10) C8B 0.0425(16) 0.0249(12) 0.0481(18) -0.0009(12) 0.0192(14) 0.0022(11) C9B 0.061(2) 0.0256(14) 0.057(2) -0.0021(13) 0.0133(17) -0.0047(13) C10B 0.0533(19) 0.0533(18) 0.053(2) -0.0142(15) 0.0282(17) 0.0069(14) C11B 0.0443(16) 0.0251(12) 0.0430(16) 0.0029(11) 0.0260(14) -0.0009(11) C12B 0.061(2) 0.0433(16) 0.066(2) 0.0129(15) 0.0388(19) -0.0121(14) C13B 0.0499(17) 0.0209(12) 0.0428(17) -0.0010(11) 0.0285(15) -0.0016(10) C14B 0.0562(19) 0.0304(14) 0.058(2) -0.0041(13) 0.0298(18) 0.0046(13) C15B 0.081(3) 0.0243(14) 0.066(2) -0.0046(13) 0.034(2) -0.0031(14) C16B 0.065(2) 0.0387(15) 0.050(2) -0.0044(14) 0.0260(18) -0.0208(14) C17B 0.0486(18) 0.0459(16) 0.0483(19) -0.0053(14) 0.0282(16) -0.0106(13) C18B 0.0457(16) 0.0316(13) 0.0456(17) -0.0054(12) 0.0288(15) -0.0056(11) O1B 0.0497(12) 0.0267(9) 0.0491(13) 0.0020(8) 0.0191(11) -0.0032(8) O2B 0.0367(11) 0.0466(11) 0.0492(13) 0.0059(9) 0.0257(10) 0.0025(8) O3B 0.0581(14) 0.0319(10) 0.0710(16) 0.0141(10) 0.0334(13) 0.0081(9) O4B 0.0458(12) 0.0341(10) 0.0602(14) 0.0134(9) 0.0338(11) -0.0005(8) C1C 0.0473(17) 0.0311(13) 0.0432(17) 0.0037(12) 0.0191(15) -0.0032(12) C2C 0.0536(18) 0.0264(13) 0.0474(18) 0.0050(12) 0.0245(15) 0.0001(11) C3C 0.0401(15) 0.0227(12) 0.0409(16) -0.0002(10) 0.0235(13) -0.0030(10) C4C 0.0433(16) 0.0242(12) 0.0508(18) -0.0025(11) 0.0305(15) -0.0033(10) C5C 0.0562(18) 0.0295(13) 0.0402(17) -0.0003(12) 0.0247(15) -0.0068(12) C6C 0.0357(15) 0.0250(12) 0.0452(17) 0.0026(11) 0.0253(14) 0.0003(10) C7C 0.0376(15) 0.0224(12) 0.0432(16) 0.0004(11) 0.0241(14) -0.0024(10) C8C 0.0448(17) 0.0245(12) 0.0461(17) -0.0015(11) 0.0216(15) 0.0023(11) C9C 0.060(2) 0.0278(14) 0.054(2) -0.0025(13) 0.0167(17) -0.0049(13) C10C 0.0498(19) 0.0486(17) 0.053(2) -0.0080(14) 0.0273(17) 0.0095(14) C11C 0.0463(16) 0.0247(12) 0.0427(17) 0.0002(11) 0.0252(14) -0.0001(11) C12C 0.069(2) 0.061(2) 0.065(2) 0.0145(17) 0.041(2) -0.0189(17) C13C 0.0446(16) 0.0232(12) 0.0412(16) -0.0009(11) 0.0269(14) -0.0029(10) C14C 0.0491(18) 0.0323(14) 0.055(2) -0.0027(13) 0.0283(16) 0.0026(12) C15C 0.078(2) 0.0270(14) 0.061(2) -0.0065(13) 0.030(2) -0.0036(14) C16C 0.072(2) 0.0473(17) 0.051(2) -0.0034(15) 0.0256(19) -0.0289(16) C17C 0.0463(18) 0.0608(19) 0.0435(18) -0.0041(15) 0.0225(16) -0.0164(14) C18C 0.0480(17) 0.0364(14) 0.0491(18) -0.0058(13) 0.0323(15) -0.0045(12) O1C 0.0418(11) 0.0291(9) 0.0452(12) 0.0019(8) 0.0176(10) -0.0008(7) O2C 0.0354(11) 0.0586(12) 0.0456(13) 0.0068(10) 0.0234(10) 0.0058(9) O3C 0.0712(16) 0.0314(11) 0.0718(16) 0.0166(10) 0.0387(14) 0.0148(10) O4C 0.0453(12) 0.0457(11) 0.0581(14) 0.0159(10) 0.0320(11) -0.0028(9) _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 O1 1.439(3) . ? C1 C2 1.521(4) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 C3 1.518(4) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.526(4) . ? C3 C7 1.534(3) . ? C3 H3A 1.0000 . ? C4 C13 1.514(3) . ? C4 C5 1.538(4) . ? C4 H4A 1.0000 . ? C5 C6 1.561(3) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 O2 1.415(3) . ? C6 C11 1.529(3) . ? C6 C7 1.547(4) . ? C7 C8 1.535(4) . ? C7 H7A 1.0000 . ? C8 O1 1.465(3) . ? C8 C9 1.513(3) . ? C8 C10 1.532(3) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 O3 1.200(3) . ? C11 O4 1.333(3) . ? C12 O4 1.449(3) . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 C18 1.386(4) . ? C13 C14 1.387(3) . ? C14 C15 1.386(4) . ? C14 H14A 0.9500 . ? C15 C16 1.378(4) . ? C15 H15A 0.9500 . ? C16 C17 1.384(4) . ? C16 H16A 0.9500 . ? C17 C18 1.398(3) . ? C17 H17A 0.9500 . ? C18 H18A 0.9500 . ? O2 H2C 0.8400 . ? C1B O1B 1.435(3) . ? C1B C2B 1.523(4) . ? C1B H1BA 0.9900 . ? C1B H1BB 0.9900 . ? C2B C3B 1.526(4) . ? C2B H2BA 0.9900 . ? C2B H2BB 0.9900 . ? C3B C7B 1.530(3) . ? C3B C4B 1.534(4) . ? C3B H3BA 1.0000 . ? C4B C13B 1.510(3) . ? C4B C5B 1.557(4) . ? C4B H4BA 1.0000 . ? C5B C6B 1.556(3) . ? C5B H5BA 0.9900 . ? C5B H5BB 0.9900 . ? C6B O2B 1.409(3) . ? C6B C11B 1.529(3) . ? C6B C7B 1.542(4) . ? C7B C8B 1.532(4) . ? C7B H7BA 1.0000 . ? C8B O1B 1.471(3) . ? C8B C9B 1.520(3) . ? C8B C10B 1.528(4) . ? C9B H9BA 0.9800 . ? C9B H9BB 0.9800 . ? C9B H9BC 0.9800 . ? C10B H10D 0.9800 . ? C10B H10E 0.9800 . ? C10B H10F 0.9800 . ? C11B O3B 1.192(3) . ? C11B O4B 1.341(3) . ? C12B O4B 1.446(3) . ? C12B H12D 0.9800 . ? C12B H12E 0.9800 . ? C12B H12F 0.9800 . ? C13B C14B 1.390(3) . ? C13B C18B 1.395(4) . ? C14B C15B 1.402(4) . ? C14B H14B 0.9500 . ? C15B C16B 1.375(5) . ? C15B H15B 0.9500 . ? C16B C17B 1.379(4) . ? C16B H16B 0.9500 . ? C17B C18B 1.375(4) . ? C17B H17B 0.9500 . ? C18B H18B 0.9500 . ? O2B H2BC 0.8400 . ? C1C O1C 1.432(3) . ? C1C C2C 1.527(4) . ? C1C H1CA 0.9900 . ? C1C H1CB 0.9900 . ? C2C C3C 1.529(4) . ? C2C H2CA 0.9900 . ? C2C H2CB 0.9900 . ? C3C C7C 1.530(3) . ? C3C C4C 1.531(4) . ? C3C H3CA 1.0000 . ? C4C C13C 1.513(3) . ? C4C C5C 1.558(4) . ? C4C H4CA 1.0000 . ? C5C C6C 1.560(3) . ? C5C H5CA 0.9900 . ? C5C H5CB 0.9900 . ? C6C O2C 1.413(3) . ? C6C C11C 1.530(3) . ? C6C C7C 1.537(4) . ? C7C C8C 1.538(4) . ? C7C H7CA 1.0000 . ? C8C O1C 1.462(4) . ? C8C C9C 1.518(3) . ? C8C C10C 1.525(4) . ? C9C H9CA 0.9800 . ? C9C H9CB 0.9800 . ? C9C H9CC 0.9800 . ? C10C H10G 0.9800 . ? C10C H10H 0.9800 . ? C10C H10I 0.9800 . ? C11C O3C 1.190(3) . ? C11C O4C 1.340(3) . ? C12C O4C 1.450(3) . ? C12C H12G 0.9800 . ? C12C H12H 0.9800 . ? C12C H12I 0.9800 . ? C13C C14C 1.391(3) . ? C13C C18C 1.396(4) . ? C14C C15C 1.397(4) . ? C14C H14C 0.9500 . ? C15C C16C 1.373(5) . ? C15C H15C 0.9500 . ? C16C C17C 1.388(5) . ? C16C H16C 0.9500 . ? C17C C18C 1.379(4) . ? C17C H17C 0.9500 . ? C18C H18C 0.9500 . ? O2C H2CC 0.8400 . ? 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 111.8(2) . . ? O1 C1 H1A 109.3 . . ? C2 C1 H1A 109.3 . . ? O1 C1 H1B 109.3 . . ? C2 C1 H1B 109.3 . . ? H1A C1 H1B 107.9 . . ? C3 C2 C1 109.7(2) . . ? C3 C2 H2A 109.7 . . ? C1 C2 H2A 109.7 . . ? C3 C2 H2B 109.7 . . ? C1 C2 H2B 109.7 . . ? H2A C2 H2B 108.2 . . ? C2 C3 C4 117.7(2) . . ? C2 C3 C7 109.3(2) . . ? C4 C3 C7 102.51(19) . . ? C2 C3 H3A 109.0 . . ? C4 C3 H3A 109.0 . . ? C7 C3 H3A 109.0 . . ? C13 C4 C3 114.4(2) . . ? C13 C4 C5 115.3(2) . . ? C3 C4 C5 102.7(2) . . ? C13 C4 H4A 108.0 . . ? C3 C4 H4A 108.0 . . ? C5 C4 H4A 108.0 . . ? C4 C5 C6 107.4(2) . . ? C4 C5 H5A 110.2 . . ? C6 C5 H5A 110.2 . . ? C4 C5 H5B 110.2 . . ? C6 C5 H5B 110.2 . . ? H5A C5 H5B 108.5 . . ? O2 C6 C11 109.6(2) . . ? O2 C6 C7 110.8(2) . . ? C11 C6 C7 111.0(2) . . ? O2 C6 C5 110.9(2) . . ? C11 C6 C5 110.8(2) . . ? C7 C6 C5 103.6(2) . . ? C3 C7 C8 112.9(2) . . ? C3 C7 C6 104.9(2) . . ? C8 C7 C6 122.2(2) . . ? C3 C7 H7A 105.1 . . ? C8 C7 H7A 105.1 . . ? C6 C7 H7A 105.1 . . ? O1 C8 C9 103.9(2) . . ? O1 C8 C10 109.3(2) . . ? C9 C8 C10 110.5(2) . . ? O1 C8 C7 105.21(19) . . ? C9 C8 C7 111.7(2) . . ? C10 C8 C7 115.4(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 . . ? C8 C10 H10A 109.5 . . ? C8 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C8 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? O3 C11 O4 123.6(2) . . ? O3 C11 C6 125.6(2) . . ? O4 C11 C6 110.8(2) . . ? O4 C12 H12A 109.5 . . ? O4 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? O4 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C18 C13 C14 117.9(2) . . ? C18 C13 C4 122.0(2) . . ? C14 C13 C4 120.1(2) . . ? C15 C14 C13 121.3(3) . . ? C15 C14 H14A 119.3 . . ? C13 C14 H14A 119.3 . . ? C16 C15 C14 120.3(3) . . ? C16 C15 H15A 119.8 . . ? C14 C15 H15A 119.8 . . ? C15 C16 C17 119.5(3) . . ? C15 C16 H16A 120.3 . . ? C17 C16 H16A 120.3 . . ? C16 C17 C18 119.8(3) . . ? C16 C17 H17A 120.1 . . ? C18 C17 H17A 120.1 . . ? C13 C18 C17 121.2(2) . . ? C13 C18 H18A 119.4 . . ? C17 C18 H18A 119.4 . . ? C1 O1 C8 115.4(2) . . ? C6 O2 H2C 109.5 . . ? C11 O4 C12 116.4(2) . . ? O1B C1B C2B 111.7(2) . . ? O1B C1B H1BA 109.3 . . ? C2B C1B H1BA 109.3 . . ? O1B C1B H1BB 109.3 . . ? C2B C1B H1BB 109.3 . . ? H1BA C1B H1BB 107.9 . . ? C1B C2B C3B 109.2(2) . . ? C1B C2B H2BA 109.8 . . ? C3B C2B H2BA 109.8 . . ? C1B C2B H2BB 109.8 . . ? C3B C2B H2BB 109.8 . . ? H2BA C2B H2BB 108.3 . . ? C2B C3B C7B 109.3(2) . . ? C2B C3B C4B 117.2(2) . . ? C7B C3B C4B 104.3(2) . . ? C2B C3B H3BA 108.6 . . ? C7B C3B H3BA 108.6 . . ? C4B C3B H3BA 108.6 . . ? C13B C4B C3B 112.5(2) . . ? C13B C4B C5B 114.6(2) . . ? C3B C4B C5B 104.64(19) . . ? C13B C4B H4BA 108.3 . . ? C3B C4B H4BA 108.3 . . ? C5B C4B H4BA 108.3 . . ? C6B C5B C4B 107.1(2) . . ? C6B C5B H5BA 110.3 . . ? C4B C5B H5BA 110.3 . . ? C6B C5B H5BB 110.3 . . ? C4B C5B H5BB 110.3 . . ? H5BA C5B H5BB 108.5 . . ? O2B C6B C11B 110.3(2) . . ? O2B C6B C7B 108.5(2) . . ? C11B C6B C7B 113.3(2) . . ? O2B C6B C5B 111.1(2) . . ? C11B C6B C5B 111.1(2) . . ? C7B C6B C5B 102.2(2) . . ? C3B C7B C8B 112.7(2) . . ? C3B C7B C6B 102.9(2) . . ? C8B C7B C6B 121.9(2) . . ? C3B C7B H7BA 106.1 . . ? C8B C7B H7BA 106.1 . . ? C6B C7B H7BA 106.1 . . ? O1B C8B C9B 103.5(2) . . ? O1B C8B C10B 109.6(2) . . ? C9B C8B C10B 109.8(2) . . ? O1B C8B C7B 105.70(19) . . ? C9B C8B C7B 111.9(2) . . ? C10B C8B C7B 115.6(2) . . ? C8B C9B H9BA 109.5 . . ? C8B C9B H9BB 109.5 . . ? H9BA C9B H9BB 109.5 . . ? C8B C9B H9BC 109.5 . . ? H9BA C9B H9BC 109.5 . . ? H9BB C9B H9BC 109.5 . . ? C8B C10B H10D 109.5 . . ? C8B C10B H10E 109.5 . . ? H10D C10B H10E 109.5 . . ? C8B C10B H10F 109.5 . . ? H10D C10B H10F 109.5 . . ? H10E C10B H10F 109.5 . . ? O3B C11B O4B 124.0(2) . . ? O3B C11B C6B 125.4(2) . . ? O4B C11B C6B 110.6(2) . . ? O4B C12B H12D 109.5 . . ? O4B C12B H12E 109.5 . . ? H12D C12B H12E 109.5 . . ? O4B C12B H12F 109.5 . . ? H12D C12B H12F 109.5 . . ? H12E C12B H12F 109.5 . . ? C14B C13B C18B 118.1(2) . . ? C14B C13B C4B 121.6(2) . . ? C18B C13B C4B 120.3(2) . . ? C13B C14B C15B 120.6(3) . . ? C13B C14B H14B 119.7 . . ? C15B C14B H14B 119.7 . . ? C16B C15B C14B 119.5(3) . . ? C16B C15B H15B 120.3 . . ? C14B C15B H15B 120.3 . . ? C15B C16B C17B 120.6(3) . . ? C15B C16B H16B 119.7 . . ? C17B C16B H16B 119.7 . . ? C18B C17B C16B 119.7(3) . . ? C18B C17B H17B 120.2 . . ? C16B C17B H17B 120.2 . . ? C17B C18B C13B 121.5(2) . . ? C17B C18B H18B 119.3 . . ? C13B C18B H18B 119.3 . . ? C1B O1B C8B 115.7(2) . . ? C6B O2B H2BC 109.5 . . ? C11B O4B C12B 116.7(2) . . ? O1C C1C C2C 111.9(2) . . ? O1C C1C H1CA 109.2 . . ? C2C C1C H1CA 109.2 . . ? O1C C1C H1CB 109.2 . . ? C2C C1C H1CB 109.2 . . ? H1CA C1C H1CB 107.9 . . ? C1C C2C C3C 109.2(2) . . ? C1C C2C H2CA 109.8 . . ? C3C C2C H2CA 109.8 . . ? C1C C2C H2CB 109.8 . . ? C3C C2C H2CB 109.8 . . ? H2CA C2C H2CB 108.3 . . ? C2C C3C C7C 109.2(2) . . ? C2C C3C C4C 116.9(2) . . ? C7C C3C C4C 103.8(2) . . ? C2C C3C H3CA 108.9 . . ? C7C C3C H3CA 108.9 . . ? C4C C3C H3CA 108.9 . . ? C13C C4C C3C 114.0(2) . . ? C13C C4C C5C 114.1(2) . . ? C3C C4C C5C 104.82(19) . . ? C13C C4C H4CA 107.8 . . ? C3C C4C H4CA 107.8 . . ? C5C C4C H4CA 107.8 . . ? C4C C5C C6C 106.7(2) . . ? C4C C5C H5CA 110.4 . . ? C6C C5C H5CA 110.4 . . ? C4C C5C H5CB 110.4 . . ? C6C C5C H5CB 110.4 . . ? H5CA C5C H5CB 108.6 . . ? O2C C6C C11C 109.4(2) . . ? O2C C6C C7C 108.7(2) . . ? C11C C6C C7C 114.6(2) . . ? O2C C6C C5C 110.9(2) . . ? C11C C6C C5C 110.1(2) . . ? C7C C6C C5C 103.0(2) . . ? C3C C7C C6C 103.1(2) . . ? C3C C7C C8C 112.8(2) . . ? C6C C7C C8C 122.0(2) . . ? C3C C7C H7CA 105.9 . . ? C6C C7C H7CA 105.9 . . ? C8C C7C H7CA 105.9 . . ? O1C C8C C9C 104.0(2) . . ? O1C C8C C10C 109.4(2) . . ? C9C C8C C10C 109.8(2) . . ? O1C C8C C7C 105.15(19) . . ? C9C C8C C7C 111.2(2) . . ? C10C C8C C7C 116.4(2) . . ? C8C C9C H9CA 109.5 . . ? C8C C9C H9CB 109.5 . . ? H9CA C9C H9CB 109.5 . . ? C8C C9C H9CC 109.5 . . ? H9CA C9C H9CC 109.5 . . ? H9CB C9C H9CC 109.5 . . ? C8C C10C H10G 109.5 . . ? C8C C10C H10H 109.5 . . ? H10G C10C H10H 109.5 . . ? C8C C10C H10I 109.5 . . ? H10G C10C H10I 109.5 . . ? H10H C10C H10I 109.5 . . ? O3C C11C O4C 123.8(2) . . ? O3C C11C C6C 125.3(2) . . ? O4C C11C C6C 110.9(2) . . ? O4C C12C H12G 109.5 . . ? O4C C12C H12H 109.5 . . ? H12G C12C H12H 109.5 . . ? O4C C12C H12I 109.5 . . ? H12G C12C H12I 109.5 . . ? H12H C12C H12I 109.5 . . ? C14C C13C C18C 118.2(2) . . ? C14C C13C C4C 121.2(2) . . ? C18C C13C C4C 120.6(2) . . ? C13C C14C C15C 120.6(3) . . ? C13C C14C H14C 119.7 . . ? C15C C14C H14C 119.7 . . ? C16C C15C C14C 120.0(3) . . ? C16C C15C H15C 120.0 . . ? C14C C15C H15C 120.0 . . ? C15C C16C C17C 120.2(3) . . ? C15C C16C H16C 119.9 . . ? C17C C16C H16C 119.9 . . ? C18C C17C C16C 119.6(3) . . ? C18C C17C H17C 120.2 . . ? C16C C17C H17C 120.2 . . ? C17C C18C C13C 121.4(3) . . ? C17C C18C H18C 119.3 . . ? C13C C18C H18C 119.3 . . ? C1C O1C C8C 115.4(2) . . ? C6C O2C H2CC 109.5 . . ? C11C O4C C12C 116.4(2) . . ? 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 -54.1(3) . . . . ? C1 C2 C3 C4 169.13(19) . . . . ? C1 C2 C3 C7 52.9(2) . . . . ? C2 C3 C4 C13 72.6(3) . . . . ? C7 C3 C4 C13 -167.5(2) . . . . ? C2 C3 C4 C5 -161.6(2) . . . . ? C7 C3 C4 C5 -41.7(2) . . . . ? C13 C4 C5 C6 152.1(2) . . . . ? C3 C4 C5 C6 26.9(2) . . . . ? C4 C5 C6 O2 -120.6(2) . . . . ? C4 C5 C6 C11 117.5(2) . . . . ? C4 C5 C6 C7 -1.7(2) . . . . ? C2 C3 C7 C8 -57.5(3) . . . . ? C4 C3 C7 C8 177.0(2) . . . . ? C2 C3 C7 C6 167.14(18) . . . . ? C4 C3 C7 C6 41.6(2) . . . . ? O2 C6 C7 C3 94.7(2) . . . . ? C11 C6 C7 C3 -143.27(19) . . . . ? C5 C6 C7 C3 -24.3(2) . . . . ? O2 C6 C7 C8 -35.4(3) . . . . ? C11 C6 C7 C8 86.6(3) . . . . ? C5 C6 C7 C8 -154.4(2) . . . . ? C3 C7 C8 O1 57.5(3) . . . . ? C6 C7 C8 O1 -175.89(19) . . . . ? C3 C7 C8 C9 169.6(2) . . . . ? C6 C7 C8 C9 -63.8(3) . . . . ? C3 C7 C8 C10 -63.1(3) . . . . ? C6 C7 C8 C10 63.5(3) . . . . ? O2 C6 C11 O3 0.4(4) . . . . ? C7 C6 C11 O3 -122.3(3) . . . . ? C5 C6 C11 O3 123.1(3) . . . . ? O2 C6 C11 O4 -177.8(2) . . . . ? C7 C6 C11 O4 59.5(3) . . . . ? C5 C6 C11 O4 -55.1(3) . . . . ? C3 C4 C13 C18 62.6(4) . . . . ? C5 C4 C13 C18 -56.3(4) . . . . ? C3 C4 C13 C14 -115.4(3) . . . . ? C5 C4 C13 C14 125.7(3) . . . . ? C18 C13 C14 C15 0.5(5) . . . . ? C4 C13 C14 C15 178.6(3) . . . . ? C13 C14 C15 C16 -0.8(5) . . . . ? C14 C15 C16 C17 0.8(5) . . . . ? C15 C16 C17 C18 -0.5(5) . . . . ? C14 C13 C18 C17 -0.2(5) . . . . ? C4 C13 C18 C17 -178.2(3) . . . . ? C16 C17 C18 C13 0.2(5) . . . . ? C2 C1 O1 C8 59.9(3) . . . . ? C9 C8 O1 C1 -176.5(2) . . . . ? C10 C8 O1 C1 65.5(3) . . . . ? C7 C8 O1 C1 -59.0(2) . . . . ? O3 C11 O4 C12 -1.0(5) . . . . ? C6 C11 O4 C12 177.3(3) . . . . ? O1B C1B C2B C3B 54.6(3) . . . . ? C1B C2B C3B C7B -53.9(3) . . . . ? C1B C2B C3B C4B -172.2(2) . . . . ? C2B C3B C4B C13B -86.8(3) . . . . ? C7B C3B C4B C13B 152.2(2) . . . . ? C2B C3B C4B C5B 148.2(2) . . . . ? C7B C3B C4B C5B 27.3(2) . . . . ? C13B C4B C5B C6B -125.5(2) . . . . ? C3B C4B C5B C6B -1.9(3) . . . . ? C4B C5B C6B O2B 91.8(3) . . . . ? C4B C5B C6B C11B -144.9(2) . . . . ? C4B C5B C6B C7B -23.7(2) . . . . ? C2B C3B C7B C8B 58.0(3) . . . . ? C4B C3B C7B C8B -175.9(2) . . . . ? C2B C3B C7B C6B -168.90(19) . . . . ? C4B C3B C7B C6B -42.8(2) . . . . ? O2B C6B C7B C3B -77.0(2) . . . . ? C11B C6B C7B C3B 160.15(19) . . . . ? C5B C6B C7B C3B 40.5(2) . . . . ? O2B C6B C7B C8B 50.5(3) . . . . ? C11B C6B C7B C8B -72.3(3) . . . . ? C5B C6B C7B C8B 168.0(2) . . . . ? C3B C7B C8B O1B -57.0(3) . . . . ? C6B C7B C8B O1B 179.97(19) . . . . ? C3B C7B C8B C9B -169.0(2) . . . . ? C6B C7B C8B C9B 68.0(3) . . . . ? C3B C7B C8B C10B 64.4(3) . . . . ? C6B C7B C8B C10B -58.7(3) . . . . ? O2B C6B C11B O3B 6.8(4) . . . . ? C7B C6B C11B O3B 128.6(3) . . . . ? C5B C6B C11B O3B -116.9(3) . . . . ? O2B C6B C11B O4B -174.4(2) . . . . ? C7B C6B C11B O4B -52.5(3) . . . . ? C5B C6B C11B O4B 61.9(3) . . . . ? C3B C4B C13B C14B 117.7(3) . . . . ? C5B C4B C13B C14B -123.0(3) . . . . ? C3B C4B C13B C18B -59.6(4) . . . . ? C5B C4B C13B C18B 59.8(3) . . . . ? C18B C13B C14B C15B 0.5(5) . . . . ? C4B C13B C14B C15B -176.8(3) . . . . ? C13B C14B C15B C16B 0.7(5) . . . . ? C14B C15B C16B C17B -1.5(5) . . . . ? C15B C16B C17B C18B 1.1(5) . . . . ? C16B C17B C18B C13B 0.2(5) . . . . ? C14B C13B C18B C17B -1.0(5) . . . . ? C4B C13B C18B C17B 176.4(3) . . . . ? C2B C1B O1B C8B -59.4(3) . . . . ? C9B C8B O1B C1B 175.9(2) . . . . ? C10B C8B O1B C1B -67.0(3) . . . . ? C7B C8B O1B C1B 58.2(3) . . . . ? O3B C11B O4B C12B -0.4(4) . . . . ? C6B C11B O4B C12B -179.2(2) . . . . ? O1C C1C C2C C3C -54.3(3) . . . . ? C1C C2C C3C C7C 52.9(3) . . . . ? C1C C2C C3C C4C 170.3(2) . . . . ? C2C C3C C4C C13C 83.8(3) . . . . ? C7C C3C C4C C13C -155.9(2) . . . . ? C2C C3C C4C C5C -150.7(2) . . . . ? C7C C3C C4C C5C -30.4(3) . . . . ? C13C C4C C5C C6C 131.9(2) . . . . ? C3C C4C C5C C6C 6.4(3) . . . . ? C4C C5C C6C O2C -96.4(3) . . . . ? C4C C5C C6C C11C 142.4(2) . . . . ? C4C C5C C6C C7C 19.7(3) . . . . ? C2C C3C C7C C6C 168.81(19) . . . . ? C4C C3C C7C C6C 43.4(2) . . . . ? C2C C3C C7C C8C -57.7(3) . . . . ? C4C C3C C7C C8C 176.9(2) . . . . ? O2C C6C C7C C3C 79.1(2) . . . . ? C11C C6C C7C C3C -158.11(19) . . . . ? C5C C6C C7C C3C -38.6(2) . . . . ? O2C C6C C7C C8C -48.8(3) . . . . ? C11C C6C C7C C8C 74.0(3) . . . . ? C5C C6C C7C C8C -166.5(2) . . . . ? C3C C7C C8C O1C 57.8(3) . . . . ? C6C C7C C8C O1C -178.60(19) . . . . ? C3C C7C C8C C9C 169.8(2) . . . . ? C6C C7C C8C C9C -66.7(3) . . . . ? C3C C7C C8C C10C -63.5(3) . . . . ? C6C C7C C8C C10C 60.1(3) . . . . ? O2C C6C C11C O3C -9.7(4) . . . . ? C7C C6C C11C O3C -132.0(3) . . . . ? C5C C6C C11C O3C 112.4(3) . . . . ? O2C C6C C11C O4C 172.3(2) . . . . ? C7C C6C C11C O4C 49.9(3) . . . . ? C5C C6C C11C O4C -65.6(3) . . . . ? C3C C4C C13C C14C -121.1(3) . . . . ? C5C C4C C13C C14C 118.5(3) . . . . ? C3C C4C C13C C18C 58.5(4) . . . . ? C5C C4C C13C C18C -61.9(3) . . . . ? C18C C13C C14C C15C -0.1(5) . . . . ? C4C C13C C14C C15C 179.6(3) . . . . ? C13C C14C C15C C16C -1.0(5) . . . . ? C14C C15C C16C C17C 1.4(5) . . . . ? C15C C16C C17C C18C -0.7(5) . . . . ? C16C C17C C18C C13C -0.4(5) . . . . ? C14C C13C C18C C17C 0.8(5) . . . . ? C4C C13C C18C C17C -178.9(3) . . . . ? C2C C1C O1C C8C 60.6(3) . . . . ? C9C C8C O1C C1C -176.5(2) . . . . ? C10C C8C O1C C1C 66.2(3) . . . . ? C7C C8C O1C C1C -59.6(3) . . . . ? O3C C11C O4C C12C -0.9(4) . . . . ? C6C C11C O4C C12C 177.2(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O2 H2C O1B 0.84 1.98 2.817(3) 175.7 1_656 O2B H2BC O1 0.84 1.99 2.776(3) 154.5 . O2C H2CC O1C 0.84 1.98 2.771(3) 157.2 4_565 _diffrn_measured_fraction_theta_max 0.951 _diffrn_reflns_theta_full 67.32 _diffrn_measured_fraction_theta_full 0.951 _refine_diff_density_max 0.395 _refine_diff_density_min -0.592 _refine_diff_density_rms 0.088