# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 1999 # CCDC Number: 188/184 # # Article submitted to J. Chem. Soc., Perkin Trans. 2 # 'Conformation of cis,trans-1,3,5-trimethyl-1,3,5- # cyclohexanetricarboxylic acid derivatives: crystal structures # and semiempirical molecular orbital calculations.' # data_global _publ_contact_author ; Pierre Thu\'ery CEA Saclay, SCM (CNRS URA 331) B\^at. 125 91191 Gif-sur-Yvette France ; _publ_contact_author_phone '16(1)69 08 63 29' _publ_contact_author_fax '16(1)69 08 66 40' _publ_contact_author_email thuery@drecam.cea.fr _publ_requested_journal 'J. Chem. Soc., Perkin Trans. 2' _publ_requested_coeditor_name ? _publ_contact_letter ? data_1a _audit_creation_method SHELXL _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C23 H32 O6' _chemical_formula_weight 404.49 _chemical_melting_point ? _chemical_compound_source ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 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 18.3529(12) _cell_length_b 6.4184(5) _cell_length_c 19.1454(13) _cell_angle_alpha 90.00 _cell_angle_beta 93.695(3) _cell_angle_gamma 90.00 _cell_volume 2251(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 20567 _cell_measurement_theta_min 2.22 _cell_measurement_theta_max 26.68 _exptl_crystal_description platelet _exptl_crystal_colour colourless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.194 _exptl_crystal_density_method ? _exptl_crystal_F_000 872 _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_type none _exptl_special_details 'see text' _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Nonius Kappa-CCD' _diffrn_measurement_method 'area detector' _diffrn_standards_decay_% none _diffrn_reflns_number 20567 _diffrn_reflns_av_R_equivalents 0.0357 _diffrn_reflns_av_sigmaI/netI 0.0469 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.22 _diffrn_reflns_theta_max 26.68 _reflns_number_total 3863 _reflns_number_observed 1762 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'Kappa-CCD software (Nonius, 1997)' _computing_cell_refinement 'HKL package (Otwinowski & Minor, 1997)' _computing_data_reduction 'HKL package (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 1997)' _computing_publication_material 'SHELXTL (Sheldrick, 1997)' _refine_special_details ; Structure solved by direct methods. All non-hydrogen atoms refined with anisotropic displacement factors.Carboxylic protons found on the Fourier-difference map and introduced as riding atoms with a displacement factor equal to 1.2 times that of the attached oxygen atom. All other hydrogen atoms introduced at calculated positions (unless in disordered parts) as riding atoms with a displacement factor equal to 1.2 (CH, CH2) or 1.5 (CH3) times that of the attached carbon atom. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0985P)^2^+1.9041P] 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 'see text' _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0134(78) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 3863 _refine_ls_number_parameters 292 _refine_ls_number_restraints 61 _refine_ls_R_factor_all 0.1682 _refine_ls_R_factor_obs 0.0783 _refine_ls_wR_factor_all 0.3331 _refine_ls_wR_factor_obs 0.1995 _refine_ls_goodness_of_fit_all 1.182 _refine_ls_goodness_of_fit_obs 1.214 _refine_ls_restrained_S_all 1.449 _refine_ls_restrained_S_obs 1.318 _refine_ls_shift/esd_max 0.004 _refine_ls_shift/esd_mean 0.001 _refine_diff_density_max 0.551 _refine_diff_density_min -0.299 _refine_diff_density_rms 0.042 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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group O1 O 0.0384(2) 0.2561(6) 0.0428(2) 0.0833(12) Uani 1 d . . H1O H 0.0719(2) 0.3401(6) 0.0064(2) 0.100 Uiso 1 d R . O2 O 0.0706(2) 0.5097(8) 0.1155(2) 0.0936(13) Uani 1 d . . O3 O -0.1338(2) 0.2715(7) -0.0189(2) 0.0998(14) Uani 1 d . . H3O H -0.1142(2) 0.3388(7) -0.0656(2) 0.120 Uiso 1 d R . O4 O -0.1057(2) 0.5378(6) 0.0517(2) 0.0892(13) Uani 1 d . . O5 O -0.1624(3) 0.0619(7) 0.2793(2) 0.110(2) Uani 1 d . . O6 O -0.0579(3) 0.1931(8) 0.3269(2) 0.113(2) Uani 1 d . . C1 C -0.0068(3) 0.2452(8) 0.1568(3) 0.0696(15) Uani 1 d . . C2 C -0.0688(3) 0.1066(8) 0.1256(3) 0.0705(15) Uani 1 d . . H2A H -0.0782(3) -0.0011(8) 0.1595(3) 0.085 Uiso 1 calc R . H2B H -0.0520(3) 0.0379(8) 0.0845(3) 0.085 Uiso 1 calc R . C3 C -0.1416(3) 0.2162(8) 0.1047(3) 0.0732(15) Uani 1 d . . C4 C -0.1679(3) 0.3450(9) 0.1658(3) 0.085(2) Uani 1 d . . H4A H -0.1822(3) 0.4817(9) 0.1482(3) 0.102 Uiso 1 calc R . H4B H -0.2113(3) 0.2789(9) 0.1819(3) 0.102 Uiso 1 calc R . C5 C -0.1136(3) 0.3740(8) 0.2286(3) 0.081(2) Uani 1 d . . C6 C -0.0369(3) 0.4176(9) 0.2046(3) 0.088(2) Uani 1 d . . H6A H -0.0036(3) 0.4333(9) 0.2457(3) 0.105 Uiso 1 calc R . H6B H -0.0379(3) 0.5488(9) 0.1795(3) 0.105 Uiso 1 calc R . C7 C 0.0358(3) 0.3466(9) 0.1017(3) 0.0697(14) Uani 1 d . . C8 C -0.1269(3) 0.3558(10) 0.0419(3) 0.0727(15) Uani 1 d . . C9 C -0.1151(4) 0.1915(10) 0.2790(4) 0.090(2) Uani 1 d . . C10 C 0.0488(3) 0.1030(10) 0.1975(3) 0.088(2) Uani 1 d . . H10A H 0.0252(3) 0.0322(10) 0.2340(3) 0.133 Uiso 1 calc R . H10B H 0.0883(3) 0.1858(10) 0.2176(3) 0.133 Uiso 1 calc R . H10C H 0.0674(3) 0.0024(10) 0.1661(3) 0.133 Uiso 1 calc R . C11 C -0.1986(3) 0.0460(10) 0.0818(4) 0.098(2) Uani 1 d . . H11A H -0.1812(3) -0.0329(10) 0.0437(4) 0.146 Uiso 1 calc R . H11B H -0.2442(3) 0.1112(10) 0.0672(4) 0.146 Uiso 1 calc R . H11C H -0.2057(3) -0.0453(10) 0.1205(4) 0.146 Uiso 1 calc R . C12 C -0.1371(5) 0.5616(10) 0.2721(4) 0.122(3) Uani 1 d . . H12A H -0.1376(5) 0.6852(10) 0.2438(4) 0.184 Uiso 1 calc R . H12B H -0.1033(5) 0.5794(10) 0.3120(4) 0.184 Uiso 1 calc R . H12C H -0.1851(5) 0.5373(10) 0.2875(4) 0.184 Uiso 1 calc R . C13 C -0.0577(5) 0.0416(14) 0.3829(3) 0.128(3) Uani 1 d . . H13A H -0.0078(5) 0.0023(14) 0.3966(3) 0.154 Uiso 1 calc R . H13B H -0.0836(5) -0.0825(14) 0.3664(3) 0.154 Uiso 1 calc R . C14 C -0.0932(4) 0.1272(11) 0.4453(3) 0.097(2) Uani 1 d U . C15 C -0.0567(5) 0.2626(16) 0.4889(5) 0.154(3) Uani 1 d U . H15A H -0.0093(5) 0.3025(16) 0.4804(5) 0.185 Uiso 1 calc R . C16 C -0.0899(5) 0.3426(15) 0.5468(4) 0.147(3) Uani 1 d U . H16A H -0.0648(5) 0.4438(15) 0.5735(4) 0.177 Uiso 1 calc R . C17 C -0.1551(3) 0.2834(10) 0.5663(3) 0.081(2) Uani 1 d U . C18 C -0.1860(4) 0.1351(12) 0.5258(4) 0.110(2) Uani 1 d U . H18A H -0.2307(4) 0.0811(12) 0.5374(4) 0.132 Uiso 1 calc R . C19 C -0.1543(4) 0.0567(12) 0.4666(4) 0.112(2) Uani 1 d U . H19A H -0.1780(4) -0.0504(12) 0.4415(4) 0.134 Uiso 1 calc R . C20 C -0.1861(3) 0.3707(11) 0.6318(3) 0.093(2) Uani 1 d D . C21 C -0.1432(6) 0.2790(23) 0.6957(4) 0.139(5) Uani 0.830(14) d PDU . C22 C -0.1783(9) 0.6089(14) 0.6336(6) 0.169(6) Uani 0.830(14) d PD . C23 C -0.2664(5) 0.3062(34) 0.6366(7) 0.190(7) Uani 0.830(14) d PDU . C25 C -0.2212(31) 0.1917(61) 0.6698(29) 0.186(9) Uani 0.170(12) d PDU . C26 C -0.1213(19) 0.4438(111) 0.6790(22) 0.138(8) Uani 0.170(12) d PDU . C24 C -0.2549(26) 0.4927(124) 0.6102(30) 0.189(10) Uani 0.170(12) d PDU . 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 0.086(3) 0.079(3) 0.088(3) -0.009(2) 0.028(2) 0.000(2) O2 0.090(3) 0.106(3) 0.086(3) -0.004(2) 0.010(2) -0.027(3) O3 0.100(3) 0.110(3) 0.089(3) 0.000(3) 0.001(2) -0.034(2) O4 0.097(3) 0.055(2) 0.120(3) 0.002(2) 0.038(2) 0.001(2) O5 0.134(4) 0.071(3) 0.127(4) 0.006(3) 0.019(3) -0.014(3) O6 0.131(4) 0.134(4) 0.076(3) -0.017(3) 0.023(3) -0.011(3) C1 0.070(3) 0.058(3) 0.082(3) -0.007(3) 0.012(3) 0.001(3) C2 0.073(3) 0.051(3) 0.089(4) -0.002(3) 0.015(3) 0.004(3) C3 0.066(3) 0.058(3) 0.097(4) -0.001(3) 0.016(3) -0.003(3) C4 0.078(4) 0.064(4) 0.118(5) 0.003(3) 0.036(4) 0.007(3) C5 0.098(4) 0.050(3) 0.101(4) -0.013(3) 0.043(4) -0.003(3) C6 0.091(4) 0.068(4) 0.106(4) -0.014(3) 0.030(3) -0.010(3) C7 0.063(3) 0.065(4) 0.083(4) -0.007(3) 0.014(3) 0.001(3) C8 0.055(3) 0.066(4) 0.098(4) 0.000(4) 0.013(3) 0.002(3) C9 0.106(5) 0.063(4) 0.105(5) -0.023(4) 0.039(4) -0.002(4) C10 0.087(4) 0.093(4) 0.086(4) 0.006(3) 0.007(3) 0.015(3) C11 0.088(4) 0.082(4) 0.124(5) 0.004(4) 0.011(4) -0.020(3) C12 0.152(6) 0.068(4) 0.155(6) -0.032(4) 0.068(5) 0.000(4) C13 0.184(8) 0.126(6) 0.077(4) -0.007(5) 0.020(5) 0.025(6) C14 0.113(4) 0.111(5) 0.069(3) -0.024(3) 0.017(3) -0.029(4) C15 0.150(5) 0.179(6) 0.141(5) -0.064(5) 0.067(5) -0.066(5) C16 0.146(5) 0.179(6) 0.122(5) -0.074(5) 0.054(4) -0.072(5) C17 0.066(3) 0.116(4) 0.060(3) -0.005(3) 0.007(3) -0.018(3) C18 0.106(4) 0.126(5) 0.100(4) -0.013(4) 0.021(4) -0.042(4) C19 0.130(5) 0.108(5) 0.097(4) -0.023(4) 0.004(4) -0.038(4) C20 0.081(4) 0.133(6) 0.063(3) 0.005(4) 0.000(3) 0.015(4) C21 0.139(8) 0.209(14) 0.069(5) 0.005(6) 0.000(5) 0.033(8) C22 0.283(17) 0.113(8) 0.119(8) -0.009(6) 0.076(9) 0.046(9) C23 0.080(6) 0.351(23) 0.143(10) -0.045(12) 0.044(6) -0.023(10) C25 0.078(13) 0.348(25) 0.137(15) -0.045(16) 0.044(12) -0.027(15) C26 0.142(13) 0.209(18) 0.061(11) 0.001(13) -0.001(11) 0.025(14) C24 0.085(12) 0.349(26) 0.139(15) -0.052(17) 0.046(12) -0.016(15) _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 C7 1.271(6) . ? O2 C7 1.246(6) . ? O3 C8 1.283(7) . ? O4 C8 1.242(6) . ? O5 C9 1.202(7) . ? O6 C9 1.348(8) . ? O6 C13 1.448(9) . ? C1 C7 1.502(8) . ? C1 C2 1.535(7) . ? C1 C10 1.542(8) . ? C1 C6 1.560(7) . ? C2 C3 1.539(7) . ? C3 C4 1.536(8) . ? C3 C8 1.537(8) . ? C3 C11 1.557(8) . ? C4 C5 1.523(9) . ? C5 C9 1.519(9) . ? C5 C6 1.534(8) . ? C5 C12 1.542(8) . ? C13 C14 1.501(9) . ? C14 C19 1.300(9) . ? C14 C15 1.353(10) . ? C15 C16 1.396(10) . ? C16 C17 1.331(9) . ? C17 C18 1.331(8) . ? C17 C20 1.519(8) . ? C18 C19 1.400(10) . ? C20 C24 1.520(12) . ? C20 C26 1.520(12) . ? C20 C25 1.524(12) . ? C20 C21 1.528(8) . ? C20 C22 1.536(9) . ? C20 C23 1.538(9) . ? C21 C26 1.18(6) . ? C21 C25 1.59(6) . ? C22 C24 1.63(8) . ? C22 C26 1.69(6) . ? C23 C25 1.25(5) . ? C23 C24 1.32(7) . ? 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 C9 O6 C13 117.6(6) . . ? C7 C1 C2 112.6(4) . . ? C7 C1 C10 104.7(4) . . ? C2 C1 C10 107.6(4) . . ? C7 C1 C6 109.0(4) . . ? C2 C1 C6 110.9(4) . . ? C10 C1 C6 111.8(5) . . ? C1 C2 C3 116.4(4) . . ? C4 C3 C8 111.2(5) . . ? C4 C3 C2 111.0(5) . . ? C8 C3 C2 106.1(4) . . ? C4 C3 C11 110.6(5) . . ? C8 C3 C11 109.7(5) . . ? C2 C3 C11 108.0(4) . . ? C5 C4 C3 116.4(5) . . ? C9 C5 C4 111.7(5) . . ? C9 C5 C6 112.7(5) . . ? C4 C5 C6 110.7(5) . . ? C9 C5 C12 104.0(5) . . ? C4 C5 C12 109.3(6) . . ? C6 C5 C12 108.2(5) . . ? C5 C6 C1 114.4(4) . . ? O2 C7 O1 121.7(5) . . ? O2 C7 C1 119.8(5) . . ? O1 C7 C1 118.4(5) . . ? O4 C8 O3 123.1(5) . . ? O4 C8 C3 119.9(6) . . ? O3 C8 C3 116.9(5) . . ? O5 C9 O6 122.2(7) . . ? O5 C9 C5 125.3(7) . . ? O6 C9 C5 112.4(6) . . ? O6 C13 C14 111.3(6) . . ? C19 C14 C15 115.7(6) . . ? C19 C14 C13 123.4(7) . . ? C15 C14 C13 120.2(7) . . ? C14 C15 C16 120.1(7) . . ? C17 C16 C15 124.3(7) . . ? C16 C17 C18 113.5(6) . . ? C16 C17 C20 121.2(6) . . ? C18 C17 C20 125.2(5) . . ? C17 C18 C19 123.0(6) . . ? C14 C19 C18 122.7(6) . . ? C17 C20 C24 108.3(24) . . ? C17 C20 C26 106.5(20) . . ? C24 C20 C26 127.4(43) . . ? C17 C20 C25 108.0(22) . . ? C24 C20 C25 98.6(37) . . ? C26 C20 C25 106.7(34) . . ? C17 C20 C21 108.5(6) . . ? C24 C20 C21 142.4(23) . . ? C26 C20 C21 45.7(24) . . ? C25 C20 C21 62.6(25) . . ? C17 C20 C22 110.2(6) . . ? C24 C20 C22 64.4(34) . . ? C26 C20 C22 67.1(28) . . ? C25 C20 C22 141.4(22) . . ? C21 C20 C22 108.8(9) . . ? C17 C20 C23 111.2(6) . . ? C24 C20 C23 51.2(30) . . ? C26 C20 C23 139.8(20) . . ? C25 C20 C23 48.2(22) . . ? C21 C20 C23 107.2(9) . . ? C22 C20 C23 110.8(11) . . ? C26 C21 C20 66.8(13) . . ? C26 C21 C25 123.2(22) . . ? C20 C21 C25 58.6(13) . . ? C20 C22 C24 57.3(17) . . ? C20 C22 C26 56.0(15) . . ? C24 C22 C26 110.4(24) . . ? C25 C23 C24 127.6(25) . . ? C25 C23 C20 65.3(11) . . ? C24 C23 C20 63.7(15) . . ? C23 C25 C20 66.5(14) . . ? C23 C25 C21 120.4(20) . . ? C20 C25 C21 58.8(13) . . ? C21 C26 C20 67.5(15) . . ? C21 C26 C22 119.4(18) . . ? C20 C26 C22 56.9(15) . . ? C23 C24 C20 65.1(17) . . ? C23 C24 C22 117.7(19) . . ? C20 C24 C22 58.3(17) . . ? #===END data_1b _audit_creation_method SHELXL _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C23 H32 O6' _chemical_formula_weight 404.49 _chemical_melting_point ? _chemical_compound_source ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 12.6745(7) _cell_length_b 18.0319(11) _cell_length_c 19.9940(11) _cell_angle_alpha 84.929(3) _cell_angle_beta 72.592(3) _cell_angle_gamma 89.799(3) _cell_volume 4342(2) _cell_formula_units_Z 8 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 32811 _cell_measurement_theta_min 2.63 _cell_measurement_theta_max 28.99 _exptl_crystal_description Platelet _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.238 _exptl_crystal_density_method ? _exptl_crystal_F_000 1744 _exptl_absorpt_coefficient_mu 0.088 _exptl_absorpt_correction_type none _exptl_special_details ? _diffrn_ambient_temperature 123(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 'Nonius Kappa-CCD' _diffrn_measurement_method 'area detector' _diffrn_standards_decay_% none _diffrn_reflns_number 32811 _diffrn_reflns_av_R_equivalents 0.082 _diffrn_reflns_av_sigmaI/netI 0.072 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 2.63 _diffrn_reflns_theta_max 28.99 _reflns_number_total 16960 _reflns_number_observed 9735 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'Kappa-CCD software (Nonius, 1997)' _computing_cell_refinement 'HKL package (Otwinowski & Minor, 1997)' _computing_data_reduction 'HKL package (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 1997)' _computing_publication_material 'SHELXTL (Sheldrick, 1997)' _refine_special_details ; Structure solved by direct methods. Carboxylic protons found on the Fourier-difference map and introduced as riding atoms with an isotropic displacement parameter equal to 1.2 times that of the attached O atom. All other hydrogen atoms introduced at calculated positions (unless for disordered parts) and constrained to ride on their parent carbon atom with displacement parameters equal to 1.2 (CH2) or 1.5 (CH3) times that of the parent atom. All non-hydrogen atoms refined anisotropically unless those of the disordered parts. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0169P)^2^+33.9531P] 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 'see text' _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0163(17) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 16960 _refine_ls_number_parameters 1045 _refine_ls_number_restraints 13 _refine_ls_R_factor_all 0.1559 _refine_ls_R_factor_obs 0.1134 _refine_ls_wR_factor_all 0.3113 _refine_ls_wR_factor_obs 0.2590 _refine_ls_goodness_of_fit_all 1.091 _refine_ls_goodness_of_fit_obs 1.162 _refine_ls_restrained_S_all 1.080 _refine_ls_restrained_S_obs 1.163 _refine_ls_shift/esd_max -0.007 _refine_ls_shift/esd_mean 0.000 _refine_diff_density_max 0.471 _refine_diff_density_min -0.487 _refine_diff_density_rms 0.079 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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group O1D O 0.3552(4) 0.9735(2) 0.5350(2) 0.0385(12) Uani 1 d . . H1D H 0.3383(4) 0.9438(2) 0.5093(2) 0.046 Uiso 1 d R . O1A O 0.2202(4) 0.4206(3) 0.1058(2) 0.0425(12) Uani 1 d . . H1A H 0.2856(4) 0.4043(3) 0.0690(2) 0.051 Uiso 1 d R . O1B O 0.6376(4) 0.6463(3) -0.0037(2) 0.0469(13) Uani 1 d . . O1C O 0.1319(5) 0.8761(3) 0.5087(3) 0.0519(15) Uani 1 d . . H1C H 0.1378(5) 0.8973(3) 0.5517(3) 0.062 Uiso 1 d R . C1D C 0.3012(5) 1.0229(3) 0.6481(3) 0.0296(15) Uani 1 d . . C1A C 0.0629(5) 0.4976(3) 0.1419(3) 0.0305(15) Uani 1 d . . C1C C 0.1647(6) 0.8696(3) 0.3846(3) 0.032(2) Uani 1 d . . C1B C 0.5357(5) 0.6441(3) 0.1199(3) 0.0292(15) Uani 1 d . . O2C O 0.3008(4) 0.9063(3) 0.4381(3) 0.0413(12) Uani 1 d . . O2A O 0.1306(4) 0.4530(2) 0.0270(2) 0.0361(11) Uani 1 d . . O2B O 0.7202(4) 0.6031(3) 0.0748(2) 0.0392(12) Uani 1 d . . H2B H 0.7818(4) 0.5824(3) 0.0397(2) 0.047 Uiso 1 d R . O2D O 0.1864(4) 0.9439(3) 0.6070(2) 0.0392(12) Uani 1 d . . C2A C 0.0011(5) 0.5567(3) 0.1095(3) 0.0291(14) Uani 1 d . . H2AA H -0.0700(5) 0.5636(3) 0.1437(3) 0.035 Uiso 1 calc R . H2AB H -0.0132(5) 0.5373(3) 0.0692(3) 0.035 Uiso 1 calc R . C2D C 0.3925(5) 1.0827(4) 0.6165(4) 0.034(2) Uani 1 d . . H2DA H 0.4479(5) 1.0630(4) 0.5777(4) 0.041 Uiso 1 calc R . H2DB H 0.4279(5) 1.0915(4) 0.6521(4) 0.041 Uiso 1 calc R . C2C C 0.1203(6) 0.9440(4) 0.3623(4) 0.034(2) Uani 1 d . . H2CA H 0.0657(6) 0.9608(4) 0.4031(4) 0.041 Uiso 1 calc R . H2CB H 0.0825(6) 0.9353(4) 0.3280(4) 0.041 Uiso 1 calc R . C2B C 0.4714(5) 0.5691(3) 0.1395(3) 0.032(2) Uani 1 d . . H2BA H 0.3998(5) 0.5773(3) 0.1726(3) 0.038 Uiso 1 calc R . H2BB H 0.4583(5) 0.5537(3) 0.0973(3) 0.038 Uiso 1 calc R . O3A O 0.2519(4) 0.6070(2) 0.0331(2) 0.0331(11) Uani 1 d . . O3D O 0.3951(4) 1.1458(3) 0.4664(2) 0.0397(12) Uani 1 d . . H3D H 0.3625(4) 1.1174(3) 0.4398(2) 0.048 Uiso 1 d R . O3B O 0.5907(4) 0.4642(2) 0.0556(2) 0.0333(11) Uani 1 d . . H3B H 0.6422(4) 0.4352(2) 0.0284(2) 0.040 Uiso 1 d R . O3C O 0.1570(4) 1.0511(3) 0.4451(2) 0.0383(12) Uani 1 d . . H3C H 0.1816(4) 1.0724(3) 0.4847(2) 0.046 Uiso 1 d R . C3B C 0.5247(5) 0.5046(3) 0.1713(3) 0.0300(15) Uani 1 d . . C3C C 0.2071(6) 1.0077(3) 0.3305(3) 0.032(2) Uani 1 d . . C3A C 0.0592(5) 0.6338(3) 0.0853(3) 0.0288(14) Uani 1 d . . C3D C 0.3560(5) 1.1581(3) 0.5895(3) 0.0309(15) Uani 1 d . . O4B O 0.6856(4) 0.4301(2) 0.1304(2) 0.0373(11) Uani 1 d . . O4D O 0.2210(4) 1.1236(3) 0.5337(2) 0.0370(11) Uani 1 d . . O4A O 0.1447(4) 0.6212(2) -0.0372(2) 0.0366(11) Uani 1 d . . H4A H 0.2171(4) 0.6045(2) -0.0601(2) 0.044 Uiso 1 d R . O4C O 0.3266(4) 1.0808(2) 0.3741(2) 0.0393(12) Uani 1 d . . C4D C 0.2588(5) 1.1895(4) 0.6472(3) 0.0312(15) Uani 1 d . . H4DA H 0.2856(5) 1.2334(4) 0.6624(3) 0.037 Uiso 1 calc R . H4DB H 0.2016(5) 1.2052(4) 0.6261(3) 0.037 Uiso 1 calc R . C4C C 0.3142(6) 0.9774(4) 0.2813(4) 0.035(2) Uani 1 d . . H4CA H 0.3401(6) 1.0120(4) 0.2395(4) 0.042 Uiso 1 calc R . H4CB H 0.3706(6) 0.9758(4) 0.3052(4) 0.042 Uiso 1 calc R . C4A C 0.0916(5) 0.6646(3) 0.1468(3) 0.0308(15) Uani 1 d . . H4AA H 0.1672(5) 0.6839(3) 0.1287(3) 0.037 Uiso 1 calc R . H4AB H 0.0446(5) 0.7061(3) 0.1625(3) 0.037 Uiso 1 calc R . C4B C 0.5824(5) 0.5311(3) 0.2243(3) 0.0306(15) Uani 1 d . . H4BA H 0.5652(5) 0.4955(3) 0.2655(3) 0.037 Uiso 1 calc R . H4BB H 0.6618(5) 0.5319(3) 0.2025(3) 0.037 Uiso 1 calc R . O5B O 0.3674(4) 0.6629(3) 0.2973(2) 0.0369(11) Uani 1 d . . O5C O 0.1698(4) 0.8454(3) 0.2092(2) 0.0393(12) Uani 1 d . . O5A O -0.1086(4) 0.6439(3) 0.2591(2) 0.0408(12) Uani 1 d . . O5D O 0.3443(4) 1.1774(3) 0.7631(3) 0.0475(13) Uani 1 d . . C5A C 0.0833(5) 0.6092(4) 0.2104(3) 0.0305(15) Uani 1 d . . C5D C 0.2063(5) 1.1352(4) 0.7123(3) 0.031(2) Uani 1 d . . C5C C 0.3016(5) 0.9003(4) 0.2587(3) 0.033(2) Uani 1 d . . C5B C 0.5468(5) 0.6094(3) 0.2478(3) 0.0295(15) Uani 1 d . . O6B O 0.4014(4) 0.5491(3) 0.3406(2) 0.0385(12) Uani 1 d . . O6A O -0.0428(4) 0.5477(3) 0.3122(2) 0.0365(11) Uani 1 d . . O6C O 0.2430(4) 0.9593(2) 0.1656(2) 0.0370(11) Uani 1 d . . O6D O 0.2316(4) 1.0810(3) 0.8176(2) 0.0422(12) Uani 1 d . . C6B C 0.5689(6) 0.6677(4) 0.1845(3) 0.034(2) Uani 1 d . . H6BA H 0.6472(6) 0.6808(4) 0.1689(3) 0.041 Uiso 1 calc R . H6BB H 0.5292(6) 0.7122(4) 0.1999(3) 0.041 Uiso 1 calc R . C6D C 0.1919(5) 1.0576(3) 0.6902(3) 0.0293(15) Uani 1 d . . H6DA H 0.1417(5) 1.0606(3) 0.6618(3) 0.035 Uiso 1 calc R . H6DB H 0.1578(5) 1.0246(3) 0.7322(3) 0.035 Uiso 1 calc R . C6C C 0.2605(6) 0.8433(4) 0.3235(4) 0.035(2) Uani 1 d . . H6CA H 0.3223(6) 0.8307(4) 0.3412(4) 0.042 Uiso 1 calc R . H6CB H 0.2364(6) 0.7982(4) 0.3087(4) 0.042 Uiso 1 calc R . C6A C 0.1261(5) 0.5336(3) 0.1873(3) 0.0278(14) Uani 1 d . . H6AA H 0.1209(5) 0.4999(3) 0.2288(3) 0.033 Uiso 1 calc R . H6AB H 0.2037(5) 0.5392(3) 0.1604(3) 0.033 Uiso 1 calc R . C7C C 0.2044(6) 0.8832(3) 0.4477(3) 0.032(2) Uani 1 d . . C7A C 0.1431(5) 0.4560(3) 0.0857(3) 0.0291(15) Uani 1 d . . C7B C 0.6378(6) 0.6321(3) 0.0592(3) 0.0287(15) Uani 1 d . . C7D C 0.2773(6) 0.9778(3) 0.5930(3) 0.032(2) Uani 1 d . . C8A C 0.1616(5) 0.6206(3) 0.0242(3) 0.0267(14) Uani 1 d . . C8D C 0.3187(6) 1.1425(3) 0.5264(3) 0.0300(15) Uani 1 d . . C8C C 0.2371(6) 1.0493(3) 0.3857(3) 0.031(2) Uani 1 d . . C8B C 0.6100(5) 0.4637(3) 0.1172(3) 0.0304(15) Uani 1 d . . C9C C 0.2283(6) 0.8974(4) 0.2109(3) 0.035(2) Uani 1 d . . C9B C 0.4282(6) 0.6109(4) 0.2958(3) 0.033(2) Uani 1 d . . C9D C 0.2705(6) 1.1347(4) 0.7652(3) 0.032(2) Uani 1 d . . C9A C -0.0340(5) 0.6036(4) 0.2613(3) 0.0307(15) Uani 1 d . . C10A C -0.0219(6) 0.4380(4) 0.1860(4) 0.038(2) Uani 1 d . . H10A H -0.0754(6) 0.4604(4) 0.2230(4) 0.056 Uiso 1 calc R . H10B H 0.0153(6) 0.3997(4) 0.2061(4) 0.056 Uiso 1 calc R . H10C H -0.0587(6) 0.4166(4) 0.1564(4) 0.056 Uiso 1 calc R . C10B C 0.4624(6) 0.7021(4) 0.0969(4) 0.037(2) Uani 1 d . . H10D H 0.3981(6) 0.7091(4) 0.1358(4) 0.055 Uiso 1 calc R . H10E H 0.4399(6) 0.6852(4) 0.0589(4) 0.055 Uiso 1 calc R . H10F H 0.5030(6) 0.7484(4) 0.0814(4) 0.055 Uiso 1 calc R . C10D C 0.3443(6) 0.9653(4) 0.6948(3) 0.035(2) Uani 1 d . . H10G H 0.3614(6) 0.9896(4) 0.7312(3) 0.052 Uiso 1 calc R . H10H H 0.4097(6) 0.9433(4) 0.6666(3) 0.052 Uiso 1 calc R . H10I H 0.2885(6) 0.9272(4) 0.7157(3) 0.052 Uiso 1 calc R . C10C C 0.0688(6) 0.8121(4) 0.4065(4) 0.041(2) Uani 1 d . . H10J H 0.0447(6) 0.8041(4) 0.3664(4) 0.062 Uiso 1 calc R . H10K H 0.0085(6) 0.8302(4) 0.4426(4) 0.062 Uiso 1 calc R . H10L H 0.0932(6) 0.7660(4) 0.4241(4) 0.062 Uiso 1 calc R . C11A C -0.0186(6) 0.6873(4) 0.0602(4) 0.037(2) Uani 1 d . . H11A H -0.0825(6) 0.6950(4) 0.0991(4) 0.056 Uiso 1 calc R . H11B H -0.0414(6) 0.6662(4) 0.0241(4) 0.056 Uiso 1 calc R . H11C H 0.0194(6) 0.7341(4) 0.0417(4) 0.056 Uiso 1 calc R . C11B C 0.4346(6) 0.4449(4) 0.2085(4) 0.037(2) Uani 1 d . . H11D H 0.3771(6) 0.4666(4) 0.2438(4) 0.055 Uiso 1 calc R . H11E H 0.4664(6) 0.4048(4) 0.2302(4) 0.055 Uiso 1 calc R . H11F H 0.4041(6) 0.4262(4) 0.1745(4) 0.055 Uiso 1 calc R . C11D C 0.4555(6) 1.2121(4) 0.5669(4) 0.040(2) Uani 1 d . . H11G H 0.4781(6) 1.2214(4) 0.6072(4) 0.060 Uiso 1 calc R . H11H H 0.4356(6) 1.2581(4) 0.5463(4) 0.060 Uiso 1 calc R . H11I H 0.5154(6) 1.1907(4) 0.5329(4) 0.060 Uiso 1 calc R . C11C C 0.1551(7) 1.0684(4) 0.2915(4) 0.043(2) Uani 1 d . . H11J H 0.1333(7) 1.0473(4) 0.2551(4) 0.065 Uiso 1 calc R . H11K H 0.2084(7) 1.1081(4) 0.2709(4) 0.065 Uiso 1 calc R . H11L H 0.0915(7) 1.0876(4) 0.3242(4) 0.065 Uiso 1 calc R . C12B C 0.6155(6) 0.6308(4) 0.2957(4) 0.040(2) Uani 1 d . . H12A H 0.6928(6) 0.6314(4) 0.2699(4) 0.061 Uiso 1 calc R . H12B H 0.6013(6) 0.5950(4) 0.3360(4) 0.061 Uiso 1 calc R . H12C H 0.5951(6) 0.6793(4) 0.3109(4) 0.061 Uiso 1 calc R . C12A C 0.1535(6) 0.6406(4) 0.2535(4) 0.038(2) Uani 1 d . . H12D H 0.1495(6) 0.6065(4) 0.2939(4) 0.057 Uiso 1 calc R . H12E H 0.1254(6) 0.6879(4) 0.2685(4) 0.057 Uiso 1 calc R . H12F H 0.2291(6) 0.6470(4) 0.2246(4) 0.057 Uiso 1 calc R . C12D C 0.0909(6) 1.1648(4) 0.7512(4) 0.038(2) Uani 1 d . . H12G H 0.0451(6) 1.1667(4) 0.7206(4) 0.057 Uiso 1 calc R . H12H H 0.0994(6) 1.2138(4) 0.7643(4) 0.057 Uiso 1 calc R . H12I H 0.0570(6) 1.1320(4) 0.7926(4) 0.057 Uiso 1 calc R . C12C C 0.4154(6) 0.8760(4) 0.2133(4) 0.046(2) Uani 1 d . . H12J H 0.4673(6) 0.8763(4) 0.2397(4) 0.069 Uiso 1 calc R . H12K H 0.4410(6) 0.9100(4) 0.1716(4) 0.069 Uiso 1 calc R . H12L H 0.4088(6) 0.8267(4) 0.2001(4) 0.069 Uiso 1 calc R . C13A C -0.1469(6) 0.5408(4) 0.3694(3) 0.039(2) Uani 1 d . . H13A H -0.1631(6) 0.4887(4) 0.3861(3) 0.046 Uiso 1 calc R . H13B H -0.2065(6) 0.5596(4) 0.3520(3) 0.046 Uiso 1 calc R . C13B C 0.2976(6) 0.5498(4) 0.3981(3) 0.040(2) Uani 1 d . . H13C H 0.2710(6) 0.4990(4) 0.4141(3) 0.048 Uiso 1 calc R . H13D H 0.2423(6) 0.5756(4) 0.3809(3) 0.048 Uiso 1 calc R . C13C C 0.1911(6) 0.9585(4) 0.1085(3) 0.043(2) Uani 1 d . . H13E H 0.1793(6) 1.0091(4) 0.0920(3) 0.051 Uiso 1 calc R . H13F H 0.1199(6) 0.9326(4) 0.1261(3) 0.051 Uiso 1 calc R . C13D C 0.2776(7) 1.0759(5) 0.8759(4) 0.048(2) Uani 1 d . . H13G H 0.3481(7) 1.1027(5) 0.8618(4) 0.058 Uiso 1 calc R . H13H H 0.2905(7) 1.0241(5) 0.8881(4) 0.058 Uiso 1 calc R . C14A C -0.1403(6) 0.5840(4) 0.4298(3) 0.034(2) Uani 1 d . . C14B C 0.3130(5) 0.5873(4) 0.4584(3) 0.032(2) Uani 1 d . . C14D C 0.2009(6) 1.1078(4) 0.9395(3) 0.035(2) Uani 1 d . . C14C C 0.2656(6) 0.9196(4) 0.0485(3) 0.033(2) Uani 1 d . . C15C C 0.3578(6) 0.9568(4) 0.0029(4) 0.038(2) Uani 1 d . . H15A H 0.3730(6) 1.0057(4) 0.0090(4) 0.045 Uiso 1 calc R . C15B C 0.2714(6) 0.6575(4) 0.4719(4) 0.038(2) Uani 1 d . . H15B H 0.2353(6) 0.6818(4) 0.4424(4) 0.046 Uiso 1 calc R . C15A C -0.0522(6) 0.5775(4) 0.4559(4) 0.038(2) Uani 1 d . . H15C H 0.0077(6) 0.5496(4) 0.4334(4) 0.045 Uiso 1 calc R . C15D C 0.2395(6) 1.1559(4) 0.9780(4) 0.045(2) Uani 1 d . . H15D H 0.3127(6) 1.1731(4) 0.9619(4) 0.054 Uiso 1 calc R . C16D C 0.1701(6) 1.1784(4) 1.0401(4) 0.042(2) Uani 1 d . . H16A H 0.1985(6) 1.2102(4) 1.0651(4) 0.051 Uiso 1 calc R . C16B C 0.2831(6) 0.6918(4) 0.5290(3) 0.036(2) Uani 1 d . . H16B H 0.2540(6) 0.7388(4) 0.5372(3) 0.043 Uiso 1 calc R . C16C C 0.4278(6) 0.9219(4) -0.0517(4) 0.040(2) Uani 1 d . . H16C H 0.4903(6) 0.9475(4) -0.0812(4) 0.048 Uiso 1 calc R . C16A C -0.0501(6) 0.6117(4) 0.5154(4) 0.043(2) Uani 1 d . . H16D H 0.0108(6) 0.6058(4) 0.5321(4) 0.051 Uiso 1 calc R . C17B C 0.3374(5) 0.6576(3) 0.5740(3) 0.032(2) Uani 1 d . . C17D C 0.0608(6) 1.1558(3) 1.0664(3) 0.035(2) Uani 1 d . . C17A C -0.1394(6) 0.6557(3) 0.5511(3) 0.037(2) Uani 1 d D . C17C C 0.4066(6) 0.8493(3) -0.0634(3) 0.032(2) Uani 1 d . . C18A C -0.2259(6) 0.6623(4) 0.5211(4) 0.038(2) Uani 1 d . . H18A H -0.2860(6) 0.6908(4) 0.5421(4) 0.046 Uiso 1 calc R . C18B C 0.3810(6) 0.5883(4) 0.5577(3) 0.035(2) Uani 1 d . . H18B H 0.4197(6) 0.5642(4) 0.5858(3) 0.042 Uiso 1 calc R . C18C C 0.3128(6) 0.8123(4) -0.0174(3) 0.040(2) Uani 1 d . . H18C H 0.2962(6) 0.7636(4) -0.0234(3) 0.048 Uiso 1 calc R . C18D C 0.0207(6) 1.1106(4) 1.0262(4) 0.039(2) Uani 1 d . . H18D H -0.0539(6) 1.0967(4) 1.0409(4) 0.046 Uiso 1 calc R . C19B C 0.3691(6) 0.5539(4) 0.5012(3) 0.036(2) Uani 1 d . . H19A H 0.3995(6) 0.5075(4) 0.4922(3) 0.043 Uiso 1 calc R . C19C C 0.2440(6) 0.8486(4) 0.0376(4) 0.041(2) Uani 1 d . . H19B H 0.1815(6) 0.8234(4) 0.0677(4) 0.050 Uiso 1 calc R . C19D C 0.0895(6) 1.0853(4) 0.9642(4) 0.041(2) Uani 1 d . . H19C H 0.0611(6) 1.0535(4) 0.9393(4) 0.049 Uiso 1 calc R . C19A C -0.2263(6) 0.6284(4) 0.4615(3) 0.038(2) Uani 1 d . . H19D H -0.2849(6) 0.6356(4) 0.4429(3) 0.045 Uiso 1 calc R . C20B C 0.3451(6) 0.6922(4) 0.6398(3) 0.036(2) Uani 1 d . . C20C C 0.4828(6) 0.8129(4) -0.1260(3) 0.036(2) Uani 1 d . . C20A C -0.1383(5) 0.6873(3) 0.6193(3) 0.041(2) Uani 1 d D . C20D C -0.0149(6) 1.1769(4) 1.1375(4) 0.041(2) Uani 1 d . . C21B C 0.4634(7) 0.6900(5) 0.6424(4) 0.051(2) Uani 1 d . . H21A H 0.4679(7) 0.7117(5) 0.6836(4) 0.076 Uiso 1 calc R . H21B H 0.5108(7) 0.7177(5) 0.6012(4) 0.076 Uiso 1 calc R . H21C H 0.4865(7) 0.6393(5) 0.6439(4) 0.076 Uiso 1 calc R . C21C C 0.6020(7) 0.8174(5) -0.1241(4) 0.057(2) Uani 1 d . . H21D H 0.6228(7) 0.8685(5) -0.1236(4) 0.086 Uiso 1 calc R . H21E H 0.6501(7) 0.7974(5) -0.1649(4) 0.086 Uiso 1 calc R . H21F H 0.6082(7) 0.7893(5) -0.0824(4) 0.086 Uiso 1 calc R . C21D C 0.0455(9) 1.2259(5) 1.1738(5) 0.079(3) Uani 1 d . . H21G H 0.1103(9) 1.2013(5) 1.1788(5) 0.118 Uiso 1 calc R . H21H H -0.0027(9) 1.2346(5) 1.2194(5) 0.118 Uiso 1 calc R . H21I H 0.0667(9) 1.2726(5) 1.1459(5) 0.118 Uiso 1 calc R . C21A C -0.1272(12) 0.6245(5) 0.6725(5) 0.051(3) Uiso 0.73(2) d PD . C22A C -0.1809(42) 0.6275(14) 0.6806(7) 0.076(13) Uiso 0.27(2) d PD . C23A C -0.2487(7) 0.7256(6) 0.6526(5) 0.047(3) Uiso 0.73(2) d PD . C24A C -0.1999(46) 0.7604(19) 0.6267(20) 0.112(19) Uiso 0.27(2) d PD . C25A C -0.0461(9) 0.7458(6) 0.6044(6) 0.055(4) Uiso 0.73(2) d PD . C26A C -0.0183(14) 0.7016(29) 0.6178(16) 0.093(16) Uiso 0.27(2) d PD . C22B C 0.2690(7) 0.6466(4) 0.7044(4) 0.044(2) Uani 1 d . . H22A H 0.1943(7) 0.6482(4) 0.7024(4) 0.066 Uiso 1 calc R . H22B H 0.2727(7) 0.6670(4) 0.7464(4) 0.066 Uiso 1 calc R . H22C H 0.2922(7) 0.5958(4) 0.7050(4) 0.066 Uiso 1 calc R . C22C C 0.4737(7) 0.8544(4) -0.1947(4) 0.047(2) Uani 1 d . . H22D H 0.4929(7) 0.9061(4) -0.1960(4) 0.070 Uiso 1 calc R . H22E H 0.3993(7) 0.8498(4) -0.1965(4) 0.070 Uiso 1 calc R . H22F H 0.5233(7) 0.8333(4) -0.2342(4) 0.070 Uiso 1 calc R . C22D C -0.1173(9) 1.2145(7) 1.1290(5) 0.094(4) Uani 1 d . . H22J H -0.0964(9) 1.2596(7) 1.0984(5) 0.141 Uiso 1 calc R . H22K H -0.1638(9) 1.2262(7) 1.1742(5) 0.141 Uiso 1 calc R . H22L H -0.1568(9) 1.1818(7) 1.1091(5) 0.141 Uiso 1 calc R . C23C C 0.4517(8) 0.7317(4) -0.1266(4) 0.061(2) Uani 1 d . . H23A H 0.3768(8) 0.7280(4) -0.1279(4) 0.091 Uiso 1 calc R . H23B H 0.4584(8) 0.7038(4) -0.0850(4) 0.091 Uiso 1 calc R . H23C H 0.5003(8) 0.7119(4) -0.1674(4) 0.091 Uiso 1 calc R . C23B C 0.3082(7) 0.7733(4) 0.6410(4) 0.053(2) Uani 1 d . . H23D H 0.2333(7) 0.7755(4) 0.6394(4) 0.079 Uiso 1 calc R . H23E H 0.3555(7) 0.8027(4) 0.6010(4) 0.079 Uiso 1 calc R . H23F H 0.3125(7) 0.7924(4) 0.6834(4) 0.079 Uiso 1 calc R . C23D C -0.0495(8) 1.1059(4) 1.1859(4) 0.057(2) Uani 1 d . . H23J H 0.0151(8) 1.0815(4) 1.1917(4) 0.085 Uiso 1 calc R . H23K H -0.0892(8) 1.0735(4) 1.1659(4) 0.085 Uiso 1 calc R . H23L H -0.0962(8) 1.1179(4) 1.2310(4) 0.085 Uiso 1 calc R . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1D 0.046(3) 0.038(3) 0.031(3) -0.018(2) -0.007(2) 0.007(2) O1A 0.049(3) 0.045(3) 0.034(3) -0.012(2) -0.010(2) 0.021(2) O1B 0.061(3) 0.044(3) 0.030(3) -0.007(2) -0.005(2) 0.021(2) O1C 0.074(4) 0.048(3) 0.031(3) -0.003(2) -0.012(3) -0.025(3) C1D 0.036(4) 0.025(3) 0.029(3) -0.007(3) -0.010(3) 0.004(3) C1A 0.033(4) 0.032(4) 0.026(3) -0.008(3) -0.007(3) 0.002(3) C1C 0.038(4) 0.027(3) 0.031(4) -0.006(3) -0.010(3) 0.002(3) C1B 0.030(3) 0.031(4) 0.026(3) -0.011(3) -0.006(3) 0.001(3) O2C 0.036(3) 0.042(3) 0.051(3) -0.020(2) -0.017(2) 0.012(2) O2A 0.041(3) 0.041(3) 0.027(3) -0.014(2) -0.008(2) 0.004(2) O2B 0.032(3) 0.044(3) 0.043(3) -0.022(2) -0.007(2) 0.007(2) O2D 0.044(3) 0.045(3) 0.028(2) -0.013(2) -0.007(2) -0.005(2) C2A 0.030(3) 0.033(4) 0.025(3) -0.010(3) -0.007(3) 0.004(3) C2D 0.031(4) 0.038(4) 0.033(4) -0.013(3) -0.007(3) 0.005(3) C2C 0.034(4) 0.038(4) 0.035(4) -0.012(3) -0.016(3) 0.009(3) C2B 0.034(4) 0.034(4) 0.025(3) -0.011(3) -0.004(3) 0.005(3) O3A 0.032(3) 0.037(3) 0.028(2) -0.011(2) -0.005(2) 0.002(2) O3D 0.049(3) 0.041(3) 0.027(3) -0.011(2) -0.006(2) -0.006(2) O3B 0.039(3) 0.034(3) 0.028(2) -0.017(2) -0.009(2) 0.009(2) O3C 0.044(3) 0.042(3) 0.031(3) -0.015(2) -0.011(2) 0.007(2) C3B 0.035(4) 0.029(3) 0.024(3) -0.009(3) -0.005(3) 0.004(3) C3C 0.042(4) 0.025(3) 0.028(3) -0.007(3) -0.009(3) 0.010(3) C3A 0.030(3) 0.032(4) 0.023(3) -0.005(3) -0.007(3) 0.007(3) C3D 0.036(4) 0.030(4) 0.029(3) -0.013(3) -0.011(3) -0.001(3) O4B 0.045(3) 0.035(3) 0.032(3) -0.011(2) -0.008(2) 0.014(2) O4D 0.041(3) 0.043(3) 0.030(3) -0.014(2) -0.011(2) 0.006(2) O4A 0.041(3) 0.042(3) 0.025(2) -0.007(2) -0.008(2) 0.012(2) O4C 0.051(3) 0.033(3) 0.032(3) -0.010(2) -0.007(2) -0.004(2) C4D 0.036(4) 0.032(4) 0.025(3) -0.007(3) -0.008(3) 0.000(3) C4C 0.039(4) 0.034(4) 0.031(4) -0.011(3) -0.007(3) 0.002(3) C4A 0.032(4) 0.026(3) 0.030(4) -0.007(3) -0.003(3) 0.006(3) C4B 0.037(4) 0.030(4) 0.028(3) -0.014(3) -0.011(3) 0.007(3) O5B 0.038(3) 0.039(3) 0.036(3) -0.014(2) -0.012(2) 0.011(2) O5C 0.040(3) 0.046(3) 0.035(3) -0.007(2) -0.015(2) -0.002(2) O5A 0.033(3) 0.045(3) 0.037(3) 0.001(2) -0.001(2) 0.009(2) O5D 0.054(3) 0.043(3) 0.054(3) -0.008(2) -0.028(3) -0.002(3) C5A 0.029(3) 0.039(4) 0.026(3) -0.015(3) -0.010(3) 0.005(3) C5D 0.031(4) 0.036(4) 0.029(3) -0.011(3) -0.009(3) 0.007(3) C5C 0.029(4) 0.036(4) 0.034(4) -0.010(3) -0.007(3) 0.004(3) C5B 0.035(4) 0.029(3) 0.030(3) -0.016(3) -0.013(3) 0.004(3) O6B 0.041(3) 0.041(3) 0.030(3) -0.010(2) -0.004(2) 0.005(2) O6A 0.039(3) 0.041(3) 0.025(2) -0.004(2) -0.002(2) 0.006(2) O6C 0.054(3) 0.028(3) 0.029(2) -0.007(2) -0.011(2) 0.005(2) O6D 0.049(3) 0.055(3) 0.024(2) -0.009(2) -0.011(2) 0.004(2) C6B 0.033(4) 0.032(4) 0.037(4) -0.016(3) -0.007(3) 0.002(3) C6D 0.033(4) 0.028(3) 0.026(3) -0.010(3) -0.006(3) 0.003(3) C6C 0.038(4) 0.035(4) 0.037(4) -0.015(3) -0.015(3) 0.012(3) C6A 0.032(3) 0.030(3) 0.020(3) -0.010(3) -0.003(3) 0.006(3) C7C 0.040(4) 0.022(3) 0.033(4) -0.006(3) -0.008(3) 0.004(3) C7A 0.035(4) 0.018(3) 0.032(4) -0.007(3) -0.005(3) 0.003(3) C7B 0.038(4) 0.020(3) 0.032(4) -0.006(3) -0.016(3) -0.003(3) C7D 0.040(4) 0.025(3) 0.031(4) -0.004(3) -0.008(3) 0.005(3) C8A 0.033(4) 0.022(3) 0.026(3) -0.009(3) -0.008(3) 0.005(3) C8D 0.038(4) 0.022(3) 0.030(4) -0.006(3) -0.008(3) 0.001(3) C8C 0.043(4) 0.019(3) 0.031(4) -0.003(3) -0.011(3) 0.006(3) C8B 0.034(4) 0.029(4) 0.029(4) -0.008(3) -0.009(3) 0.000(3) C9C 0.034(4) 0.037(4) 0.030(4) -0.012(3) -0.004(3) 0.008(3) C9B 0.036(4) 0.031(4) 0.031(4) -0.014(3) -0.006(3) -0.001(3) C9D 0.037(4) 0.032(4) 0.025(4) -0.007(3) -0.007(3) 0.007(3) C9A 0.029(4) 0.035(4) 0.028(4) -0.010(3) -0.006(3) 0.001(3) C10A 0.043(4) 0.037(4) 0.030(4) -0.006(3) -0.006(3) -0.003(3) C10B 0.038(4) 0.038(4) 0.034(4) -0.013(3) -0.009(3) 0.007(3) C10D 0.045(4) 0.031(4) 0.030(4) -0.006(3) -0.014(3) 0.002(3) C10C 0.049(4) 0.037(4) 0.042(4) -0.008(3) -0.019(4) 0.002(3) C11A 0.038(4) 0.038(4) 0.033(4) 0.000(3) -0.007(3) 0.008(3) C11B 0.045(4) 0.029(4) 0.032(4) -0.010(3) -0.003(3) -0.004(3) C11D 0.039(4) 0.044(4) 0.035(4) -0.002(3) -0.007(3) -0.002(3) C11C 0.063(5) 0.033(4) 0.036(4) -0.008(3) -0.016(4) 0.015(3) C12B 0.038(4) 0.055(5) 0.034(4) -0.022(3) -0.014(3) 0.003(3) C12A 0.040(4) 0.043(4) 0.033(4) -0.018(3) -0.010(3) 0.007(3) C12D 0.039(4) 0.029(4) 0.041(4) -0.009(3) -0.004(3) 0.005(3) C12C 0.033(4) 0.058(5) 0.049(5) -0.030(4) -0.008(4) 0.012(3) C13A 0.037(4) 0.045(4) 0.028(4) -0.002(3) -0.002(3) -0.003(3) C13B 0.036(4) 0.053(5) 0.028(4) -0.008(3) -0.004(3) -0.003(3) C13C 0.054(5) 0.050(4) 0.025(4) -0.010(3) -0.011(3) 0.012(4) C13D 0.050(5) 0.072(5) 0.026(4) -0.010(4) -0.015(4) 0.014(4) C14A 0.035(4) 0.037(4) 0.026(3) 0.002(3) -0.001(3) 0.002(3) C14B 0.034(4) 0.033(4) 0.025(3) -0.007(3) -0.001(3) 0.001(3) C14D 0.037(4) 0.044(4) 0.026(3) -0.005(3) -0.009(3) 0.011(3) C14C 0.045(4) 0.034(4) 0.024(3) -0.009(3) -0.013(3) 0.005(3) C15C 0.048(4) 0.030(4) 0.037(4) -0.009(3) -0.013(4) 0.001(3) C15B 0.042(4) 0.040(4) 0.035(4) -0.009(3) -0.013(3) 0.010(3) C15A 0.036(4) 0.045(4) 0.033(4) -0.011(3) -0.008(3) 0.007(3) C15D 0.036(4) 0.063(5) 0.035(4) -0.004(4) -0.009(3) -0.005(4) C16D 0.057(5) 0.042(4) 0.030(4) -0.014(3) -0.013(4) 0.000(3) C16B 0.044(4) 0.030(4) 0.035(4) -0.008(3) -0.011(3) 0.007(3) C16C 0.042(4) 0.038(4) 0.036(4) -0.003(3) -0.007(3) -0.007(3) C16A 0.041(4) 0.047(4) 0.040(4) -0.002(3) -0.013(4) 0.002(3) C17B 0.033(4) 0.029(4) 0.030(4) -0.004(3) 0.000(3) -0.002(3) C17D 0.043(4) 0.024(3) 0.032(4) 0.002(3) -0.004(3) 0.007(3) C17A 0.050(4) 0.030(4) 0.029(4) 0.001(3) -0.011(3) -0.005(3) C17C 0.043(4) 0.026(3) 0.029(4) -0.005(3) -0.015(3) 0.001(3) C18A 0.044(4) 0.033(4) 0.039(4) -0.012(3) -0.012(4) 0.011(3) C18B 0.043(4) 0.032(4) 0.032(4) -0.006(3) -0.014(3) 0.006(3) C18C 0.058(5) 0.032(4) 0.029(4) -0.003(3) -0.013(4) -0.002(3) C18D 0.036(4) 0.041(4) 0.034(4) -0.003(3) -0.004(3) 0.003(3) C19B 0.042(4) 0.031(4) 0.032(4) -0.008(3) -0.005(3) 0.010(3) C19C 0.050(4) 0.039(4) 0.032(4) -0.005(3) -0.007(3) -0.005(3) C19D 0.049(5) 0.037(4) 0.040(4) -0.010(3) -0.017(4) -0.001(3) C19A 0.046(4) 0.039(4) 0.029(4) -0.006(3) -0.012(3) 0.009(3) C20B 0.048(4) 0.030(4) 0.028(4) -0.005(3) -0.008(3) -0.006(3) C20C 0.050(4) 0.027(4) 0.028(4) -0.008(3) -0.007(3) 0.002(3) C20A 0.056(5) 0.028(4) 0.037(4) -0.003(3) -0.008(4) -0.004(3) C20D 0.059(5) 0.031(4) 0.029(4) -0.008(3) -0.006(3) 0.013(3) C21B 0.056(5) 0.061(5) 0.035(4) -0.011(4) -0.012(4) -0.007(4) C21C 0.060(5) 0.064(6) 0.049(5) -0.018(4) -0.015(4) 0.024(4) C21D 0.101(8) 0.069(6) 0.057(6) -0.030(5) -0.003(6) -0.007(6) C22B 0.062(5) 0.035(4) 0.027(4) -0.003(3) -0.001(4) -0.003(3) C22C 0.059(5) 0.056(5) 0.025(4) -0.011(3) -0.011(4) 0.004(4) C22D 0.089(8) 0.122(9) 0.054(6) -0.005(6) 0.002(5) 0.072(7) C23C 0.098(7) 0.034(4) 0.039(4) -0.016(3) -0.001(5) 0.004(4) C23B 0.076(6) 0.035(4) 0.042(4) -0.015(3) -0.006(4) -0.003(4) C23D 0.077(6) 0.055(5) 0.031(4) -0.005(4) -0.005(4) 0.018(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1D C7D 1.287(8) . ? O1A C7A 1.306(8) . ? O1B C7B 1.261(8) . ? O1C C7C 1.285(8) . ? C1D C7D 1.524(9) . ? C1D C2D 1.534(9) . ? C1D C10D 1.543(9) . ? C1D C6D 1.552(8) . ? C1A C7A 1.523(8) . ? C1A C2A 1.531(9) . ? C1A C10A 1.537(9) . ? C1A C6A 1.557(9) . ? C1C C7C 1.529(9) . ? C1C C10C 1.534(9) . ? C1C C2C 1.536(9) . ? C1C C6C 1.550(9) . ? C1B C7B 1.516(9) . ? C1B C10B 1.528(9) . ? C1B C2B 1.539(9) . ? C1B C6B 1.565(9) . ? O2C C7C 1.245(8) . ? O2A C7A 1.237(8) . ? O2B C7B 1.274(8) . ? O2D C7D 1.249(8) . ? C2A C3A 1.545(9) . ? C2D C3D 1.540(9) . ? C2C C3C 1.547(9) . ? C2B C3B 1.529(9) . ? O3A C8A 1.230(8) . ? O3D C8D 1.294(8) . ? O3B C8B 1.325(8) . ? O3C C8C 1.314(8) . ? C3B C8B 1.522(9) . ? C3B C11B 1.541(9) . ? C3B C4B 1.561(9) . ? C3C C8C 1.526(9) . ? C3C C11C 1.547(9) . ? C3C C4C 1.549(9) . ? C3A C8A 1.528(8) . ? C3A C11A 1.536(9) . ? C3A C4A 1.554(9) . ? C3D C8D 1.522(9) . ? C3D C11D 1.527(9) . ? C3D C4D 1.557(9) . ? O4B C8B 1.215(8) . ? O4D C8D 1.248(8) . ? O4A C8A 1.306(8) . ? O4C C8C 1.220(8) . ? C4D C5D 1.535(9) . ? C4C C5C 1.523(9) . ? C4A C5A 1.525(9) . ? C4B C5B 1.550(8) . ? O5B C9B 1.208(8) . ? O5C C9C 1.206(8) . ? O5A C9A 1.200(8) . ? O5D C9D 1.203(8) . ? C5A C6A 1.524(8) . ? C5A C9A 1.528(9) . ? C5A C12A 1.551(9) . ? C5D C9D 1.515(10) . ? C5D C6D 1.532(9) . ? C5D C12D 1.553(9) . ? C5C C9C 1.522(10) . ? C5C C6C 1.540(9) . ? C5C C12C 1.543(9) . ? C5B C9B 1.524(9) . ? C5B C6B 1.531(9) . ? C5B C12B 1.545(9) . ? O6B C9B 1.343(8) . ? O6B C13B 1.465(8) . ? O6A C9A 1.347(8) . ? O6A C13A 1.462(8) . ? O6C C9C 1.351(8) . ? O6C C13C 1.478(8) . ? O6D C9D 1.339(8) . ? O6D C13D 1.447(8) . ? C13A C14A 1.516(10) . ? C13B C14B 1.495(9) . ? C13C C14C 1.513(9) . ? C13D C14D 1.511(9) . ? C14A C15A 1.368(10) . ? C14A C19A 1.379(9) . ? C14B C19B 1.368(10) . ? C14B C15B 1.386(9) . ? C14D C15D 1.389(10) . ? C14D C19D 1.398(10) . ? C14C C19C 1.361(9) . ? C14C C15C 1.380(10) . ? C15C C16C 1.382(10) . ? C15B C16B 1.392(10) . ? C15A C16A 1.395(10) . ? C15D C16D 1.383(10) . ? C16D C17D 1.376(10) . ? C16B C17B 1.390(10) . ? C16C C17C 1.391(9) . ? C16A C17A 1.424(10) . ? C17B C18B 1.391(9) . ? C17B C20B 1.534(9) . ? C17D C18D 1.390(10) . ? C17D C20D 1.537(9) . ? C17A C18A 1.398(10) . ? C17A C20A 1.528(8) . ? C17C C18C 1.395(10) . ? C17C C20C 1.533(9) . ? C18A C19A 1.388(10) . ? C18B C19B 1.381(9) . ? C18C C19C 1.395(10) . ? C18D C19D 1.398(10) . ? C20B C21B 1.515(11) . ? C20B C22B 1.534(9) . ? C20B C23B 1.534(10) . ? C20C C23C 1.520(10) . ? C20C C21C 1.525(11) . ? C20C C22C 1.540(10) . ? C20A C21A 1.520(8) . ? C20A C25A 1.520(8) . ? C20A C24A 1.524(10) . ? C20A C22A 1.527(10) . ? C20A C26A 1.534(10) . ? C20A C23A 1.548(8) . ? C20D C22D 1.510(12) . ? C20D C23D 1.516(10) . ? C20D C21D 1.532(12) . ? C21A C22A 0.65(5) . ? C21A C26A 1.97(4) . ? C23A C24A 0.89(6) . ? C24A C25A 1.89(5) . ? C25A C26A 0.92(5) . ? 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 C7D C1D C2D 113.2(5) . . ? C7D C1D C10D 104.3(5) . . ? C2D C1D C10D 107.5(6) . . ? C7D C1D C6D 108.6(5) . . ? C2D C1D C6D 111.3(5) . . ? C10D C1D C6D 111.7(5) . . ? C7A C1A C2A 111.6(5) . . ? C7A C1A C10A 104.8(5) . . ? C2A C1A C10A 108.0(5) . . ? C7A C1A C6A 109.9(5) . . ? C2A C1A C6A 110.8(5) . . ? C10A C1A C6A 111.6(5) . . ? C7C C1C C10C 110.4(6) . . ? C7C C1C C2C 106.2(5) . . ? C10C C1C C2C 107.9(6) . . ? C7C C1C C6C 111.0(5) . . ? C10C C1C C6C 110.3(5) . . ? C2C C1C C6C 110.9(5) . . ? C7B C1B C10B 110.4(5) . . ? C7B C1B C2B 106.4(5) . . ? C10B C1B C2B 108.3(5) . . ? C7B C1B C6B 110.6(5) . . ? C10B C1B C6B 110.9(5) . . ? C2B C1B C6B 110.0(5) . . ? C1A C2A C3A 116.7(5) . . ? C1D C2D C3D 116.3(6) . . ? C1C C2C C3C 116.2(6) . . ? C3B C2B C1B 117.3(6) . . ? C8B C3B C2B 114.0(5) . . ? C8B C3B C11B 104.4(5) . . ? C2B C3B C11B 108.6(6) . . ? C8B C3B C4B 107.6(5) . . ? C2B C3B C4B 111.7(5) . . ? C11B C3B C4B 110.4(5) . . ? C8C C3C C11C 103.2(5) . . ? C8C C3C C2C 113.5(5) . . ? C11C C3C C2C 108.5(6) . . ? C8C C3C C4C 108.7(6) . . ? C11C C3C C4C 112.1(5) . . ? C2C C3C C4C 110.7(5) . . ? C8A C3A C11A 110.4(5) . . ? C8A C3A C2A 105.4(5) . . ? C11A C3A C2A 109.3(5) . . ? C8A C3A C4A 111.2(5) . . ? C11A C3A C4A 110.4(5) . . ? C2A C3A C4A 110.1(5) . . ? C8D C3D C11D 110.4(5) . . ? C8D C3D C2D 105.6(5) . . ? C11D C3D C2D 108.5(6) . . ? C8D C3D C4D 110.3(5) . . ? C11D C3D C4D 110.9(5) . . ? C2D C3D C4D 111.0(5) . . ? C5D C4D C3D 115.4(5) . . ? C5C C4C C3C 114.7(6) . . ? C5A C4A C3A 115.9(5) . . ? C5B C4B C3B 113.4(5) . . ? C4A C5A C6A 110.8(5) . . ? C4A C5A C9A 111.7(6) . . ? C6A C5A C9A 112.2(5) . . ? C4A C5A C12A 108.0(5) . . ? C6A C5A C12A 109.8(5) . . ? C9A C5A C12A 104.1(5) . . ? C9D C5D C6D 112.8(5) . . ? C9D C5D C4D 111.6(5) . . ? C6D C5D C4D 110.3(5) . . ? C9D C5D C12D 104.6(5) . . ? C6D C5D C12D 109.2(5) . . ? C4D C5D C12D 108.0(5) . . ? C9C C5C C4C 114.2(6) . . ? C9C C5C C6C 110.7(6) . . ? C4C C5C C6C 110.5(5) . . ? C9C C5C C12C 104.0(5) . . ? C4C C5C C12C 108.8(6) . . ? C6C C5C C12C 108.4(6) . . ? C9B C5B C6B 112.1(6) . . ? C9B C5B C12B 103.0(5) . . ? C6B C5B C12B 108.8(5) . . ? C9B C5B C4B 113.4(5) . . ? C6B C5B C4B 111.2(5) . . ? C12B C5B C4B 107.9(5) . . ? C9B O6B C13B 116.9(5) . . ? C9A O6A C13A 116.8(5) . . ? C9C O6C C13C 116.7(5) . . ? C9D O6D C13D 118.5(6) . . ? C5B C6B C1B 115.9(5) . . ? C5D C6D C1D 114.4(5) . . ? C5C C6C C1C 115.2(5) . . ? C5A C6A C1A 114.1(5) . . ? O2C C7C O1C 122.7(6) . . ? O2C C7C C1C 120.0(6) . . ? O1C C7C C1C 117.0(6) . . ? O2A C7A O1A 123.4(6) . . ? O2A C7A C1A 121.3(6) . . ? O1A C7A C1A 115.2(6) . . ? O1B C7B O2B 122.2(6) . . ? O1B C7B C1B 120.8(6) . . ? O2B C7B C1B 116.9(6) . . ? O2D C7D O1D 122.8(6) . . ? O2D C7D C1D 119.5(6) . . ? O1D C7D C1D 117.6(6) . . ? O3A C8A O4A 122.8(5) . . ? O3A C8A C3A 122.1(5) . . ? O4A C8A C3A 115.0(6) . . ? O4D C8D O3D 122.8(6) . . ? O4D C8D C3D 121.0(6) . . ? O3D C8D C3D 116.1(6) . . ? O4C C8C O3C 123.3(6) . . ? O4C C8C C3C 122.3(6) . . ? O3C C8C C3C 114.4(6) . . ? O4B C8B O3B 122.7(6) . . ? O4B C8B C3B 123.0(6) . . ? O3B C8B C3B 114.1(6) . . ? O5C C9C O6C 122.9(7) . . ? O5C C9C C5C 125.8(6) . . ? O6C C9C C5C 111.1(6) . . ? O5B C9B O6B 123.3(6) . . ? O5B C9B C5B 124.8(6) . . ? O6B C9B C5B 111.6(6) . . ? O5D C9D O6D 123.2(6) . . ? O5D C9D C5D 125.9(6) . . ? O6D C9D C5D 110.8(6) . . ? O5A C9A O6A 123.2(6) . . ? O5A C9A C5A 126.2(6) . . ? O6A C9A C5A 110.6(6) . . ? O6A C13A C14A 110.8(5) . . ? O6B C13B C14B 111.3(6) . . ? O6C C13C C14C 109.5(6) . . ? O6D C13D C14D 111.4(6) . . ? C15A C14A C19A 118.6(7) . . ? C15A C14A C13A 121.2(6) . . ? C19A C14A C13A 120.1(7) . . ? C19B C14B C15B 118.2(6) . . ? C19B C14B C13B 121.2(6) . . ? C15B C14B C13B 120.6(6) . . ? C15D C14D C19D 118.0(6) . . ? C15D C14D C13D 121.6(7) . . ? C19D C14D C13D 120.2(7) . . ? C19C C14C C15C 118.5(6) . . ? C19C C14C C13C 121.8(6) . . ? C15C C14C C13C 119.7(6) . . ? C14C C15C C16C 120.6(6) . . ? C14B C15B C16B 120.8(7) . . ? C14A C15A C16A 121.6(6) . . ? C16D C15D C14D 120.6(7) . . ? C17D C16D C15D 122.5(7) . . ? C17B C16B C15B 121.5(6) . . ? C15C C16C C17C 121.4(6) . . ? C15A C16A C17A 121.2(7) . . ? C16B C17B C18B 116.2(6) . . ? C16B C17B C20B 122.4(6) . . ? C18B C17B C20B 121.3(6) . . ? C16D C17D C18D 116.9(6) . . ? C16D C17D C20D 122.8(7) . . ? C18D C17D C20D 120.3(6) . . ? C18A C17A C16A 115.0(6) . . ? C18A C17A C20A 125.2(6) . . ? C16A C17A C20A 119.7(6) . . ? C16C C17C C18C 117.6(6) . . ? C16C C17C C20C 120.4(6) . . ? C18C C17C C20C 121.9(6) . . ? C19A C18A C17A 123.1(6) . . ? C19B C18B C17B 122.4(6) . . ? C17C C18C C19C 119.8(6) . . ? C17D C18D C19D 121.8(7) . . ? C14B C19B C18B 120.8(6) . . ? C14C C19C C18C 122.0(7) . . ? C14D C19D C18D 120.1(7) . . ? C14A C19A C18A 120.5(7) . . ? C21B C20B C17B 109.7(6) . . ? C21B C20B C22B 110.0(6) . . ? C17B C20B C22B 107.9(5) . . ? C21B C20B C23B 108.6(6) . . ? C17B C20B C23B 112.1(6) . . ? C22B C20B C23B 108.5(6) . . ? C23C C20C C21C 108.6(7) . . ? C23C C20C C17C 112.7(6) . . ? C21C C20C C17C 109.7(6) . . ? C23C C20C C22C 107.3(6) . . ? C21C C20C C22C 109.7(6) . . ? C17C C20C C22C 108.8(6) . . ? C21A C20A C25A 112.0(8) . . ? C21A C20A C24A 132.7(17) . . ? C25A C20A C24A 76.6(23) . . ? C21A C20A C22A 24.8(18) . . ? C25A C20A C22A 130.9(16) . . ? C24A C20A C22A 115.4(25) . . ? C21A C20A C17A 109.8(5) . . ? C25A C20A C17A 110.2(6) . . ? C24A C20A C17A 109.8(9) . . ? C22A C20A C17A 109.1(9) . . ? C21A C20A C26A 80.3(20) . . ? C25A C20A C26A 35.1(19) . . ? C24A C20A C26A 109.3(26) . . ? C22A C20A C26A 103.6(24) . . ? C17A C20A C26A 109.5(9) . . ? C21A C20A C23A 106.9(7) . . ? C25A C20A C23A 107.5(7) . . ? C24A C20A C23A 33.8(23) . . ? C22A C20A C23A 84.6(19) . . ? C17A C20A C23A 110.5(6) . . ? C26A C20A C23A 133.7(14) . . ? C22D C20D C23D 108.7(7) . . ? C22D C20D C21D 110.4(8) . . ? C23D C20D C21D 106.2(7) . . ? C22D C20D C17D 111.1(6) . . ? C23D C20D C17D 108.1(5) . . ? C21D C20D C17D 112.1(7) . . ? C22A C21A C20A 78.2(14) . . ? C22A C21A C26A 125.1(21) . . ? C20A C21A C26A 50.2(10) . . ? C21A C22A C20A 77.0(14) . . ? C24A C23A C20A 71.7(12) . . ? C23A C24A C20A 74.5(15) . . ? C23A C24A C25A 121.5(16) . . ? C20A C24A C25A 51.6(12) . . ? C26A C25A C20A 73.3(12) . . ? C26A C25A C24A 121.3(19) . . ? C20A C25A C24A 51.8(12) . . ? C25A C26A C20A 71.6(12) . . ? C25A C26A C21A 116.6(14) . . ? C20A C26A C21A 49.5(10) . . ? #===END data_2 _audit_creation_method SHELXL _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C20 H26 O6' _chemical_formula_weight 362.41 _chemical_melting_point ? _chemical_compound_source ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 12.3657(7) _cell_length_b 13.0496(5) _cell_length_c 13.4977(7) _cell_angle_alpha 61.992(3) _cell_angle_beta 76.774(2) _cell_angle_gamma 88.767(3) _cell_volume 1863(2) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 14083 _cell_measurement_theta_min 3.04 _cell_measurement_theta_max 28.95 _exptl_crystal_description Parallelepipedic _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.292 _exptl_crystal_density_method ? _exptl_crystal_F_000 776 _exptl_absorpt_coefficient_mu 0.095 _exptl_absorpt_correction_type none _exptl_special_details ? _diffrn_ambient_temperature 123(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 'Nonius Kappa-CCD' _diffrn_measurement_method 'area detector' _diffrn_standards_decay_% none _diffrn_reflns_number 14083 _diffrn_reflns_av_R_equivalents 0.039 _diffrn_reflns_av_sigmaI/netI 0.042 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.04 _diffrn_reflns_theta_max 28.95 _reflns_number_total 7221 _reflns_number_observed 6109 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'Kappa-CCD software (Nonius, 1997)' _computing_cell_refinement 'HKL package (Otwinowski & Minor, 1997)' _computing_data_reduction 'HKL package (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 1997)' _computing_publication_material 'SHELXTL (Sheldrick, 1997)' _refine_special_details ; Structure solved by direct methods. All non-hydrogen atoms refined anisotropically. Carboxylic protons found on the Fourier-difference map and introduced as riding atoms with a displacement factor equal to 1.2 times that of the parent oxygen atom. All other hydrogen atoms introduced at calculated positions and constrained to ride on their parent carbon atom with a displacement factor equal to 1.2 (CH, CH2) or 1.5 (CH3) times that of the parent carbon atom. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0755P)^2^+0.8689P] 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 'see text' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7221 _refine_ls_number_parameters 469 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0551 _refine_ls_R_factor_obs 0.0456 _refine_ls_wR_factor_all 0.1299 _refine_ls_wR_factor_obs 0.1183 _refine_ls_goodness_of_fit_all 0.917 _refine_ls_goodness_of_fit_obs 0.918 _refine_ls_restrained_S_all 0.926 _refine_ls_restrained_S_obs 0.918 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/esd_mean 0.000 _refine_diff_density_max 0.254 _refine_diff_density_min -0.318 _refine_diff_density_rms 0.040 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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group O1A O 0.53947(9) 0.07232(10) 0.30895(9) 0.0317(2) Uani 1 d . . C1A C 0.47857(12) -0.06370(14) 0.25476(13) 0.0281(3) Uani 1 d . . O1B O -0.05840(9) -0.56521(10) 0.68653(9) 0.0324(2) Uani 1 d . . H1B H -0.00163(9) -0.57665(10) 0.64461(9) 0.039 Uiso 1 d R . C1B C -0.15429(12) -0.42480(13) 0.73108(13) 0.0292(3) Uani 1 d . . O2A O 0.61816(9) -0.09483(11) 0.36140(10) 0.0350(3) Uani 1 d . . H2A H 0.66127(9) -0.07905(11) 0.41487(10) 0.042 Uiso 1 d R . C2A C 0.37321(13) -0.13262(13) 0.35339(13) 0.0290(3) Uani 1 d . . H2AA H 0.33131(13) -0.17307(13) 0.32729(13) 0.035 Uiso 1 calc R . H2AB H 0.39737(13) -0.19146(13) 0.41933(13) 0.035 Uiso 1 calc R . C2B C -0.21695(13) -0.36549(13) 0.63405(13) 0.0301(3) Uani 1 d . . H2B1 H -0.27505(13) -0.32489(13) 0.65812(13) 0.036 Uiso 1 calc R . H2B2 H -0.16482(13) -0.30720(13) 0.56520(13) 0.036 Uiso 1 calc R . O2B O 0.03869(10) -0.39595(11) 0.62731(11) 0.0396(3) Uani 1 d . . O3A O 0.30647(10) 0.05309(10) 0.49124(10) 0.0351(3) Uani 1 d . . C3B C -0.27071(12) -0.44653(13) 0.60110(12) 0.0282(3) Uani 1 d . . C3A C 0.29402(12) -0.06032(13) 0.39462(12) 0.0278(3) Uani 1 d . . O3B O -0.20343(10) -0.56793(10) 0.51456(10) 0.0365(3) Uani 1 d . . H3B H -0.13912(10) -0.58046(10) 0.46138(10) 0.044 Uiso 1 d R . O4A O 0.38863(10) -0.11243(10) 0.54590(9) 0.0340(3) Uani 1 d . . H4A H 0.41927(10) -0.09038(10) 0.59865(9) 0.041 Uiso 1 d R . C4A C 0.27864(12) 0.05531(13) 0.29053(12) 0.0266(3) Uani 1 d . . H4AA H 0.19985(12) 0.06655(13) 0.30147(12) 0.032 Uiso 1 calc R . H4AB H 0.31728(12) 0.11942(13) 0.29018(12) 0.032 Uiso 1 calc R . C4B C -0.32867(12) -0.56072(13) 0.71044(12) 0.0275(3) Uani 1 d . . H4BA H -0.40159(12) -0.57723(13) 0.70289(12) 0.033 Uiso 1 calc R . H4BB H -0.28508(12) -0.62449(13) 0.71392(12) 0.033 Uiso 1 calc R . O4B O -0.10321(9) -0.39885(10) 0.45027(9) 0.0340(3) Uani 1 d . . O5B O -0.41035(9) -0.40902(11) 0.87983(10) 0.0366(3) Uani 1 d . . O5A O 0.29638(10) -0.07615(12) 0.10134(11) 0.0411(3) Uani 1 d . . C5A C 0.32183(12) 0.06031(13) 0.17181(12) 0.0263(3) Uani 1 d . . C5B C -0.34328(12) -0.55658(13) 0.82490(12) 0.0268(3) Uani 1 d . . O6B O -0.51102(9) -0.46803(10) 0.79387(9) 0.0304(2) Uani 1 d . . O6A O 0.14874(9) -0.04227(10) 0.20941(9) 0.0306(2) Uani 1 d . . C6A C 0.44697(12) 0.04318(14) 0.15241(12) 0.0287(3) Uani 1 d . . H6AA H 0.48838(12) 0.11301(14) 0.13827(12) 0.034 Uiso 1 calc R . H6AB H 0.47034(12) 0.03446(14) 0.08333(12) 0.034 Uiso 1 calc R . C6B C -0.22877(12) -0.53101(14) 0.83902(13) 0.0297(3) Uani 1 d . . H6BA H -0.18884(12) -0.59980(14) 0.85641(13) 0.036 Uiso 1 calc R . H6BB H -0.24014(12) -0.51682(14) 0.90489(13) 0.036 Uiso 1 calc R . C7A C 0.55174(12) -0.02413(13) 0.30966(12) 0.0272(3) Uani 1 d . . C7B C -0.04908(12) -0.46361(13) 0.67903(12) 0.0283(3) Uani 1 d . . C8A C 0.33386(12) -0.03550(13) 0.48115(12) 0.0274(3) Uani 1 d . . C8B C -0.18441(13) -0.47273(13) 0.51729(12) 0.0284(3) Uani 1 d . . C9A C 0.25748(13) -0.02798(14) 0.15706(13) 0.0285(3) Uani 1 d . . C9B C -0.42221(12) -0.46851(13) 0.83573(12) 0.0279(3) Uani 1 d . . C10A C 0.53865(14) -0.1458(2) 0.21332(15) 0.0361(4) Uani 1 d . . H10A H 0.49182(14) -0.1701(2) 0.17892(15) 0.054 Uiso 1 calc R . H10B H 0.55449(14) -0.2129(2) 0.27807(15) 0.054 Uiso 1 calc R . H10C H 0.60726(14) -0.1057(2) 0.15703(15) 0.054 Uiso 1 calc R . C10B C -0.12083(15) -0.3345(2) 0.7640(2) 0.0376(4) Uani 1 d . . H10D H -0.18680(15) -0.3098(2) 0.7967(2) 0.056 Uiso 1 calc R . H10E H -0.07774(15) -0.2684(2) 0.6962(2) 0.056 Uiso 1 calc R . H10F H -0.07703(15) -0.3689(2) 0.8199(2) 0.056 Uiso 1 calc R . C11A C 0.18174(14) -0.13609(15) 0.46762(14) 0.0347(4) Uani 1 d . . H11A H 0.14924(14) -0.15662(15) 0.42040(14) 0.052 Uiso 1 calc R . H11B H 0.13180(14) -0.09289(15) 0.49572(14) 0.052 Uiso 1 calc R . H11C H 0.19451(14) -0.20576(15) 0.53202(14) 0.052 Uiso 1 calc R . C11B C -0.35456(14) -0.3799(2) 0.52940(14) 0.0366(4) Uani 1 d . . H11D H -0.41264(14) -0.3595(2) 0.57582(14) 0.055 Uiso 1 calc R . H11E H -0.38665(14) -0.4286(2) 0.50585(14) 0.055 Uiso 1 calc R . H11F H -0.31636(14) -0.3102(2) 0.46207(14) 0.055 Uiso 1 calc R . C12A C 0.30446(13) 0.18045(14) 0.07671(13) 0.0304(3) Uani 1 d . . H12A H 0.34309(13) 0.24068(14) 0.08105(13) 0.046 Uiso 1 calc R . H12B H 0.22619(13) 0.19019(14) 0.08772(13) 0.046 Uiso 1 calc R . H12C H 0.33326(13) 0.18534(14) 0.00210(13) 0.046 Uiso 1 calc R . C12B C -0.39851(13) -0.67618(14) 0.92561(13) 0.0311(3) Uani 1 d . . H12D H -0.35291(13) -0.73610(14) 0.92394(13) 0.047 Uiso 1 calc R . H12E H -0.47095(13) -0.69095(14) 0.91768(13) 0.047 Uiso 1 calc R . H12F H -0.40605(13) -0.67595(14) 0.99789(13) 0.047 Uiso 1 calc R . C13B C -0.59263(13) -0.38932(15) 0.80253(15) 0.0339(3) Uani 1 d . . H13A H -0.55619(13) -0.31144(15) 0.77057(15) 0.041 Uiso 1 calc R . H13B H -0.63070(13) -0.41578(15) 0.88298(15) 0.041 Uiso 1 calc R . C13A C 0.07812(14) -0.12351(15) 0.2011(2) 0.0347(4) Uani 1 d . . H13C H 0.10485(14) -0.20017(15) 0.2319(2) 0.042 Uiso 1 calc R . H13D H 0.07753(14) -0.09707(15) 0.1210(2) 0.042 Uiso 1 calc R . C14B C -0.67521(13) -0.38837(15) 0.73499(14) 0.0350(4) Uani 1 d . . H14A H -0.72106(13) -0.32483(15) 0.72613(14) 0.042 Uiso 1 calc R . H14B H -0.63421(13) -0.37299(15) 0.65817(14) 0.042 Uiso 1 calc R . C14A C -0.03776(14) -0.12780(14) 0.27176(15) 0.0363(4) Uani 1 d . . H14C H -0.08608(14) -0.18786(14) 0.27566(15) 0.044 Uiso 1 calc R . H14D H -0.03406(14) -0.14956(14) 0.35012(15) 0.044 Uiso 1 calc R . C15A C -0.08851(12) -0.01385(14) 0.22311(13) 0.0315(3) Uani 1 d . . C15B C -0.75053(13) -0.50012(14) 0.79006(13) 0.0315(3) Uani 1 d . . C16A C -0.14503(14) 0.01511(15) 0.13655(14) 0.0348(3) Uani 1 d . . H16A H -0.15130(14) -0.03680(15) 0.10850(14) 0.042 Uiso 1 calc R . C16B C -0.84859(14) -0.5189(2) 0.8742(2) 0.0394(4) Uani 1 d . . H16B H -0.86703(14) -0.4623(2) 0.8969(2) 0.047 Uiso 1 calc R . C17A C -0.19211(14) 0.1199(2) 0.09146(15) 0.0373(4) Uani 1 d . . H17A H -0.22945(14) 0.1378(2) 0.03368(15) 0.045 Uiso 1 calc R . C17B C -0.9190(2) -0.6210(2) 0.9246(2) 0.0446(4) Uani 1 d . . H17B H -0.9844(2) -0.6321(2) 0.9803(2) 0.054 Uiso 1 calc R . C18A C -0.18331(14) 0.1977(2) 0.13279(15) 0.0366(4) Uani 1 d . . H18A H -0.21553(14) 0.2676(2) 0.10351(15) 0.044 Uiso 1 calc R . C18B C -0.8926(2) -0.7059(2) 0.8924(2) 0.0448(4) Uani 1 d . . H18B H -0.9400(2) -0.7742(2) 0.9261(2) 0.054 Uiso 1 calc R . C19A C -0.12636(14) 0.1711(2) 0.2179(2) 0.0386(4) Uani 1 d . . H19A H -0.11933(14) 0.2237(2) 0.2450(2) 0.046 Uiso 1 calc R . C19B C -0.7950(2) -0.6890(2) 0.8096(2) 0.0427(4) Uani 1 d . . H19B H -0.7765(2) -0.7462(2) 0.7879(2) 0.051 Uiso 1 calc R . C20A C -0.07992(14) 0.0661(2) 0.26277(14) 0.0359(4) Uani 1 d . . H20A H -0.04239(14) 0.0487(2) 0.32031(14) 0.043 Uiso 1 calc R . C20B C -0.72496(14) -0.5868(2) 0.75918(15) 0.0370(4) Uani 1 d . . H20B H -0.65962(14) -0.5762(2) 0.70358(15) 0.044 Uiso 1 calc R . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1A 0.0383(6) 0.0285(6) 0.0305(5) -0.0152(4) -0.0097(5) 0.0023(5) C1A 0.0287(7) 0.0301(8) 0.0286(7) -0.0160(6) -0.0081(6) 0.0042(6) O1B 0.0320(6) 0.0295(6) 0.0320(5) -0.0155(4) 0.0005(4) 0.0028(4) C1B 0.0275(7) 0.0289(8) 0.0292(7) -0.0154(6) 0.0006(6) -0.0005(6) O2A 0.0358(6) 0.0405(7) 0.0359(6) -0.0213(5) -0.0162(5) 0.0140(5) C2A 0.0328(8) 0.0267(8) 0.0279(7) -0.0125(6) -0.0092(6) 0.0007(6) C2B 0.0316(7) 0.0245(8) 0.0277(7) -0.0111(6) 0.0011(6) 0.0017(6) O2B 0.0299(6) 0.0468(7) 0.0428(7) -0.0276(6) 0.0049(5) -0.0098(5) O3A 0.0410(6) 0.0374(7) 0.0322(6) -0.0211(5) -0.0085(5) 0.0052(5) C3B 0.0283(7) 0.0273(8) 0.0257(7) -0.0117(6) -0.0029(6) 0.0044(6) C3A 0.0290(7) 0.0285(8) 0.0255(7) -0.0128(6) -0.0058(6) -0.0018(6) O3B 0.0372(6) 0.0381(7) 0.0346(6) -0.0220(5) 0.0010(5) -0.0015(5) O4A 0.0408(6) 0.0324(6) 0.0279(5) -0.0119(4) -0.0121(5) -0.0005(5) C4A 0.0267(7) 0.0277(8) 0.0260(7) -0.0141(6) -0.0043(6) 0.0008(6) C4B 0.0275(7) 0.0270(8) 0.0273(7) -0.0143(6) -0.0025(6) 0.0014(6) O4B 0.0348(6) 0.0299(6) 0.0278(5) -0.0106(4) 0.0025(4) 0.0011(5) O5B 0.0321(6) 0.0420(7) 0.0437(7) -0.0293(5) -0.0037(5) 0.0021(5) O5A 0.0376(6) 0.0532(8) 0.0512(7) -0.0394(6) -0.0127(6) 0.0088(6) C5A 0.0275(7) 0.0278(8) 0.0243(7) -0.0132(5) -0.0060(5) 0.0024(6) C5B 0.0255(7) 0.0262(8) 0.0255(7) -0.0118(5) -0.0012(5) 0.0004(6) O6B 0.0262(5) 0.0322(6) 0.0358(6) -0.0200(5) -0.0046(4) 0.0051(4) O6A 0.0271(5) 0.0330(6) 0.0357(6) -0.0195(5) -0.0075(4) -0.0001(4) C6A 0.0291(7) 0.0314(8) 0.0241(7) -0.0127(6) -0.0051(6) 0.0020(6) C6B 0.0273(7) 0.0327(8) 0.0261(7) -0.0134(6) -0.0026(6) 0.0013(6) C7A 0.0263(7) 0.0288(8) 0.0249(7) -0.0124(6) -0.0043(6) 0.0022(6) C7B 0.0282(7) 0.0294(8) 0.0253(7) -0.0132(6) -0.0025(6) -0.0011(6) C8A 0.0267(7) 0.0298(8) 0.0232(7) -0.0119(6) -0.0029(5) -0.0020(6) C8B 0.0289(7) 0.0291(8) 0.0243(7) -0.0110(6) -0.0050(6) 0.0032(6) C9A 0.0297(7) 0.0300(8) 0.0284(7) -0.0153(6) -0.0091(6) 0.0055(6) C9B 0.0262(7) 0.0290(8) 0.0245(7) -0.0125(6) 0.0012(6) -0.0032(6) C10A 0.0385(9) 0.0406(10) 0.0399(9) -0.0265(7) -0.0129(7) 0.0093(7) C10B 0.0354(8) 0.0382(10) 0.0419(9) -0.0251(7) -0.0006(7) -0.0026(7) C11A 0.0340(8) 0.0375(9) 0.0275(7) -0.0126(6) -0.0038(6) -0.0075(7) C11B 0.0352(8) 0.0396(10) 0.0295(8) -0.0132(7) -0.0063(6) 0.0118(7) C12A 0.0338(8) 0.0306(8) 0.0265(7) -0.0128(6) -0.0084(6) 0.0034(6) C12B 0.0325(8) 0.0279(8) 0.0276(7) -0.0118(6) -0.0007(6) -0.0001(6) C13B 0.0292(8) 0.0304(9) 0.0432(9) -0.0209(7) -0.0036(7) 0.0061(6) C13A 0.0356(8) 0.0300(9) 0.0441(9) -0.0195(7) -0.0159(7) 0.0025(7) C14B 0.0324(8) 0.0324(9) 0.0337(8) -0.0127(6) -0.0036(6) 0.0062(6) C14A 0.0342(8) 0.0301(9) 0.0383(8) -0.0100(6) -0.0111(7) -0.0044(7) C15A 0.0256(7) 0.0328(9) 0.0297(7) -0.0112(6) -0.0030(6) -0.0031(6) C15B 0.0303(8) 0.0342(9) 0.0304(7) -0.0150(6) -0.0096(6) 0.0071(6) C16A 0.0360(8) 0.0350(9) 0.0351(8) -0.0172(7) -0.0106(7) 0.0010(7) C16B 0.0350(9) 0.0436(10) 0.0388(9) -0.0221(7) -0.0022(7) 0.0026(7) C17A 0.0364(9) 0.0414(10) 0.0342(8) -0.0173(7) -0.0111(7) 0.0052(7) C17B 0.0352(9) 0.0520(12) 0.0389(9) -0.0188(8) -0.0008(7) -0.0044(8) C18A 0.0326(8) 0.0387(10) 0.0368(8) -0.0184(7) -0.0052(7) 0.0066(7) C18B 0.0411(10) 0.0428(11) 0.0471(10) -0.0155(8) -0.0177(8) -0.0033(8) C19A 0.0348(8) 0.0457(11) 0.0416(9) -0.0271(8) -0.0067(7) 0.0051(7) C19B 0.0411(9) 0.0430(11) 0.0547(11) -0.0279(8) -0.0211(8) 0.0071(8) C20A 0.0313(8) 0.0445(10) 0.0339(8) -0.0201(7) -0.0085(6) 0.0032(7) C20B 0.0334(8) 0.0439(10) 0.0387(9) -0.0233(7) -0.0105(7) 0.0067(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1A C7A 1.260(2) . ? C1A C7A 1.523(2) . ? C1A C10A 1.533(2) . ? C1A C2A 1.553(2) . ? C1A C6A 1.556(2) . ? O1B C7B 1.287(2) . ? C1B C7B 1.527(2) . ? C1B C10B 1.534(2) . ? C1B C2B 1.550(2) . ? C1B C6B 1.561(2) . ? O2A C7A 1.280(2) . ? C2A C3A 1.537(2) . ? C2B C3B 1.538(2) . ? O2B C7B 1.249(2) . ? O3A C8A 1.257(2) . ? C3B C8B 1.527(2) . ? C3B C11B 1.548(2) . ? C3B C4B 1.552(2) . ? C3A C8A 1.529(2) . ? C3A C11A 1.547(2) . ? C3A C4A 1.551(2) . ? O3B C8B 1.288(2) . ? O4A C8A 1.284(2) . ? C4A C5A 1.539(2) . ? C4B C5B 1.540(2) . ? O4B C8B 1.250(2) . ? O5B C9B 1.207(2) . ? O5A C9A 1.207(2) . ? C5A C9A 1.526(2) . ? C5A C6A 1.539(2) . ? C5A C12A 1.541(2) . ? C5B C9B 1.529(2) . ? C5B C6B 1.535(2) . ? C5B C12B 1.542(2) . ? O6B C9B 1.344(2) . ? O6B C13B 1.450(2) . ? O6A C9A 1.340(2) . ? O6A C13A 1.447(2) . ? C13B C14B 1.513(2) . ? C13A C14A 1.514(2) . ? C14B C15B 1.507(2) . ? C14A C15A 1.506(2) . ? C15A C20A 1.394(2) . ? C15A C16A 1.394(2) . ? C15B C20B 1.386(2) . ? C15B C16B 1.393(2) . ? C16A C17A 1.387(3) . ? C16B C17B 1.387(3) . ? C17A C18A 1.385(2) . ? C17B C18B 1.376(3) . ? C18A C19A 1.387(2) . ? C18B C19B 1.384(3) . ? C19A C20A 1.385(3) . ? C19B C20B 1.385(3) . ? 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 C7A C1A C10A 110.19(13) . . ? C7A C1A C2A 105.31(12) . . ? C10A C1A C2A 108.97(13) . . ? C7A C1A C6A 110.66(12) . . ? C10A C1A C6A 110.53(12) . . ? C2A C1A C6A 111.06(12) . . ? C7B C1B C10B 109.22(12) . . ? C7B C1B C2B 106.18(12) . . ? C10B C1B C2B 108.89(13) . . ? C7B C1B C6B 111.06(13) . . ? C10B C1B C6B 110.55(12) . . ? C2B C1B C6B 110.82(12) . . ? C3A C2A C1A 116.13(12) . . ? C3B C2B C1B 116.21(13) . . ? C8B C3B C2B 110.77(12) . . ? C8B C3B C11B 103.60(12) . . ? C2B C3B C11B 108.69(13) . . ? C8B C3B C4B 111.11(13) . . ? C2B C3B C4B 111.12(12) . . ? C11B C3B C4B 111.29(13) . . ? C8A C3A C2A 111.98(12) . . ? C8A C3A C11A 102.85(11) . . ? C2A C3A C11A 108.34(12) . . ? C8A C3A C4A 110.40(12) . . ? C2A C3A C4A 111.01(12) . . ? C11A C3A C4A 112.01(13) . . ? C5A C4A C3A 114.37(12) . . ? C5B C4B C3B 114.10(12) . . ? C9A C5A C6A 110.35(12) . . ? C9A C5A C12A 105.04(12) . . ? C6A C5A C12A 109.55(12) . . ? C9A C5A C4A 113.40(12) . . ? C6A C5A C4A 109.54(12) . . ? C12A C5A C4A 108.83(12) . . ? C9B C5B C6B 110.24(12) . . ? C9B C5B C4B 113.65(12) . . ? C6B C5B C4B 109.69(12) . . ? C9B C5B C12B 105.05(11) . . ? C6B C5B C12B 109.68(12) . . ? C4B C5B C12B 108.37(12) . . ? C9B O6B C13B 115.97(12) . . ? C9A O6A C13A 116.95(12) . . ? C5A C6A C1A 114.65(12) . . ? C5B C6B C1B 114.71(12) . . ? O1A C7A O2A 122.91(14) . . ? O1A C7A C1A 119.19(13) . . ? O2A C7A C1A 117.74(13) . . ? O2B C7B O1B 123.16(14) . . ? O2B C7B C1B 120.25(14) . . ? O1B C7B C1B 116.49(13) . . ? O3A C8A O4A 123.19(13) . . ? O3A C8A C3A 119.85(13) . . ? O4A C8A C3A 116.80(13) . . ? O4B C8B O3B 123.17(14) . . ? O4B C8B C3B 119.24(14) . . ? O3B C8B C3B 117.44(13) . . ? O5A C9A O6A 122.89(14) . . ? O5A C9A C5A 125.54(14) . . ? O6A C9A C5A 111.49(12) . . ? O5B C9B O6B 123.01(14) . . ? O5B C9B C5B 125.41(14) . . ? O6B C9B C5B 111.53(12) . . ? O6B C13B C14B 107.46(13) . . ? O6A C13A C14A 106.23(13) . . ? C15B C14B C13B 114.26(14) . . ? C15A C14A C13A 113.42(13) . . ? C20A C15A C16A 118.0(2) . . ? C20A C15A C14A 121.03(14) . . ? C16A C15A C14A 121.0(2) . . ? C20B C15B C16B 118.1(2) . . ? C20B C15B C14B 121.50(15) . . ? C16B C15B C14B 120.4(2) . . ? C17A C16A C15A 121.3(2) . . ? C17B C16B C15B 120.9(2) . . ? C18A C17A C16A 119.8(2) . . ? C18B C17B C16B 120.3(2) . . ? C19A C18A C17A 119.9(2) . . ? C17B C18B C19B 119.6(2) . . ? C20A C19A C18A 120.0(2) . . ? C20B C19B C18B 120.0(2) . . ? C19A C20A C15A 121.1(2) . . ? C15B C20B C19B 121.2(2) . . ? #===END data_3 _audit_creation_method SHELXL _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C20 H27 N O5' _chemical_formula_weight 361.43 _chemical_melting_point ? _chemical_compound_source ? 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' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbcn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' '-x, y, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' 'x, -y, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 24.3829(15) _cell_length_b 9.8960(6) _cell_length_c 15.7266(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3795(2) _cell_formula_units_Z 8 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Parallelepipedic _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.40 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.265 _exptl_crystal_density_method ? _exptl_crystal_F_000 1552 _exptl_absorpt_coefficient_mu 0.090 _exptl_absorpt_correction_type none _exptl_special_details 'see text' _diffrn_ambient_temperature 123(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 'Nonius Kappa-CCD' _diffrn_measurement_method 'area detector' _diffrn_standards_decay_% none _diffrn_reflns_number 25229 _diffrn_reflns_av_R_equivalents 0.059 _diffrn_reflns_av_sigmaI/netI 0.044 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.34 _diffrn_reflns_theta_max 28.19 _reflns_number_total 3527 _reflns_number_observed 2808 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'Kappa-CCD software (Nonius, 1997)' _computing_cell_refinement 'HKL package (Otwinowski & Minor, 1997)' _computing_data_reduction 'HKL package (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 1997)' _computing_publication_material 'SHELXTL (Sheldrick, 1997)' _refine_special_details ; Structure solved by direct methods. All non-hydrogen atoms refined anisotropically. Carboxylic protons found on the Fourier-difference map and introduced as riding atoms with a displacement factor equal to 1.2 times that of the parent atom. All other hydrogen atoms introduced at calculated positions as riding atoms with a displacement factor equal to 1.2 (CH, CH2) or 1.5 (CH3) times that of the parent atom. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0781P)^2^+3.2260P] 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 'see text' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3527 _refine_ls_number_parameters 241 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0821 _refine_ls_R_factor_obs 0.0632 _refine_ls_wR_factor_all 0.1887 _refine_ls_wR_factor_obs 0.1581 _refine_ls_goodness_of_fit_all 1.037 _refine_ls_goodness_of_fit_obs 1.068 _refine_ls_restrained_S_all 1.138 _refine_ls_restrained_S_obs 1.068 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/esd_mean 0.000 _refine_diff_density_max 0.637 _refine_diff_density_min -0.301 _refine_diff_density_rms 0.049 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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group O1 O 0.52741(9) 0.4210(3) 0.15446(13) 0.0646(7) Uani 1 d . . H1 H 0.5068(15) 0.3430(36) 0.1145(25) 0.078 Uiso 1 d . . O2 O 0.58466(7) 0.4241(2) 0.04604(12) 0.0476(5) Uani 1 d . . O3 O 0.48400(8) 0.6737(3) 0.06571(14) 0.0685(7) Uani 1 d . . H3 H 0.4596(17) 0.6379(39) 0.0126(26) 0.082 Uiso 1 d . . O4 O 0.53079(7) 0.7450(2) -0.04742(12) 0.0458(5) Uani 1 d . . O5 O 0.73118(7) 0.8774(2) 0.03788(11) 0.0364(4) Uani 1 d . . N N 0.76068(7) 0.6629(2) 0.02924(12) 0.0287(4) Uani 1 d . . H0A H 0.75255(7) 0.5784(2) 0.03119(12) 0.034 Uiso 1 calc R . C1 C 0.60397(9) 0.5734(3) 0.16432(15) 0.0358(5) Uani 1 d . . C2 C 0.57092(9) 0.7054(3) 0.1744(2) 0.0407(6) Uani 1 d . . H2A H 0.53416(9) 0.6823(3) 0.1930(2) 0.049 Uiso 1 calc R . H2B H 0.58772(9) 0.7587(3) 0.2192(2) 0.049 Uiso 1 calc R . C3 C 0.56637(9) 0.7938(3) 0.0945(2) 0.0384(6) Uani 1 d . . C4 C 0.62347(9) 0.8228(2) 0.0582(2) 0.0346(5) Uani 1 d . . H4A H 0.64185(9) 0.8852(2) 0.0963(2) 0.042 Uiso 1 calc R . H4B H 0.61890(9) 0.8685(2) 0.0042(2) 0.042 Uiso 1 calc R . C5 C 0.66154(8) 0.7008(2) 0.04420(14) 0.0277(5) Uani 1 d . . C6 C 0.65966(8) 0.6042(2) 0.12205(14) 0.0311(5) Uani 1 d . . H6A H 0.67555(8) 0.5188(2) 0.10457(14) 0.037 Uiso 1 calc R . H6B H 0.68353(8) 0.6417(2) 0.16539(14) 0.037 Uiso 1 calc R . C7 C 0.57141(9) 0.4686(2) 0.11505(15) 0.0330(5) Uani 1 d . . C8 C 0.52622(9) 0.7359(3) 0.0297(2) 0.0387(6) Uani 1 d . . C9 C 0.72085(9) 0.7553(2) 0.03735(14) 0.0270(4) Uani 1 d . . C10 C 0.61494(11) 0.5117(3) 0.2528(2) 0.0466(7) Uani 1 d . . H10A H 0.63555(11) 0.5745(3) 0.2865(2) 0.070 Uiso 1 calc R . H10B H 0.63542(11) 0.4294(3) 0.2465(2) 0.070 Uiso 1 calc R . H10C H 0.58065(11) 0.4927(3) 0.2803(2) 0.070 Uiso 1 calc R . C11 C 0.53990(11) 0.9307(3) 0.1202(2) 0.0548(8) Uani 1 d . . H11A H 0.56270(11) 0.9750(3) 0.1614(2) 0.082 Uiso 1 calc R . H11B H 0.50430(11) 0.9146(3) 0.1442(2) 0.082 Uiso 1 calc R . H11C H 0.53635(11) 0.9870(3) 0.0708(2) 0.082 Uiso 1 calc R . C12 C 0.65044(10) 0.6305(2) -0.04175(15) 0.0352(5) Uani 1 d . . H12A H 0.67489(10) 0.5552(2) -0.04820(15) 0.053 Uiso 1 calc R . H12B H 0.65632(10) 0.6936(2) -0.08723(15) 0.053 Uiso 1 calc R . H12C H 0.61320(10) 0.5991(2) -0.04326(15) 0.053 Uiso 1 calc R . C13 C 0.81760(9) 0.7036(2) 0.01715(15) 0.0312(5) Uani 1 d . . H13A H 0.84136(9) 0.6288(2) 0.03222(15) 0.037 Uiso 1 calc R . H13B H 0.82582(9) 0.7780(2) 0.05521(15) 0.037 Uiso 1 calc R . C14 C 0.82997(10) 0.7470(2) -0.0742(2) 0.0363(5) Uani 1 d . . H14A H 0.80314(10) 0.8139(2) -0.0915(2) 0.044 Uiso 1 calc R . H14B H 0.86578(10) 0.7896(2) -0.0757(2) 0.044 Uiso 1 calc R . C15 C 0.82928(9) 0.6325(2) -0.13731(14) 0.0330(5) Uani 1 d . . C16 C 0.78643(11) 0.6152(3) -0.1945(2) 0.0498(7) Uani 1 d . . H16A H 0.75722(11) 0.6756(3) -0.1952(2) 0.060 Uiso 1 calc R . C17 C 0.7876(2) 0.5055(4) -0.2514(2) 0.0678(10) Uani 1 d . . H17A H 0.7590(2) 0.4939(4) -0.2899(2) 0.081 Uiso 1 calc R . C18 C 0.8301(2) 0.4160(3) -0.2506(2) 0.0628(9) Uani 1 d . . H18A H 0.8302(2) 0.3437(3) -0.2884(2) 0.075 Uiso 1 calc R . C19 C 0.87217(15) 0.4318(3) -0.1951(2) 0.0558(8) Uani 1 d . . H19A H 0.90104(15) 0.3704(3) -0.1947(2) 0.067 Uiso 1 calc R . C20 C 0.87199(11) 0.5389(3) -0.1393(2) 0.0401(6) Uani 1 d . . H20A H 0.90122(11) 0.5492(3) -0.1019(2) 0.048 Uiso 1 calc R . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0571(12) 0.093(2) 0.0440(13) -0.0183(11) 0.0149(9) -0.0386(12) O2 0.0298(9) 0.0625(12) 0.0504(12) -0.0225(9) 0.0055(7) -0.0084(8) O3 0.0412(11) 0.116(2) 0.0486(13) -0.0215(12) 0.0009(8) -0.0277(12) O4 0.0379(10) 0.0537(11) 0.0457(13) 0.0015(8) -0.0116(7) -0.0059(8) O5 0.0357(9) 0.0241(9) 0.0496(11) -0.0009(7) -0.0001(7) -0.0028(6) N 0.0253(9) 0.0245(9) 0.0362(11) 0.0006(7) 0.0013(7) -0.0028(7) C1 0.0308(11) 0.0501(14) 0.0263(13) -0.0013(10) -0.0013(8) -0.0073(10) C2 0.0300(12) 0.061(2) 0.0315(14) -0.0151(11) 0.0010(9) -0.0059(11) C3 0.0265(11) 0.0459(14) 0.043(2) -0.0162(10) -0.0047(9) 0.0032(10) C4 0.0288(11) 0.0328(12) 0.0422(14) -0.0049(9) -0.0064(9) 0.0021(9) C5 0.0248(10) 0.0276(11) 0.0307(12) -0.0008(8) -0.0034(7) -0.0006(8) C6 0.0249(10) 0.0388(12) 0.0297(13) 0.0009(9) -0.0044(8) -0.0027(9) C7 0.0264(11) 0.0443(13) 0.0282(13) 0.0025(9) -0.0001(8) 0.0001(9) C8 0.0258(11) 0.0510(15) 0.039(2) -0.0115(10) -0.0031(9) 0.0084(10) C9 0.0292(11) 0.0250(11) 0.0268(12) -0.0002(8) -0.0013(8) -0.0004(8) C10 0.0457(14) 0.065(2) 0.0291(15) 0.0034(11) -0.0028(10) -0.0170(12) C11 0.0359(14) 0.060(2) 0.069(2) -0.0301(15) -0.0120(12) 0.0139(13) C12 0.0353(12) 0.0358(12) 0.0344(14) -0.0036(9) -0.0056(9) -0.0019(10) C13 0.0250(10) 0.0331(12) 0.0355(13) -0.0023(9) 0.0019(8) -0.0041(9) C14 0.0385(12) 0.0330(12) 0.0374(14) 0.0005(9) 0.0049(9) -0.0084(10) C15 0.0327(11) 0.0380(12) 0.0281(13) 0.0037(9) 0.0024(8) -0.0088(9) C16 0.0409(14) 0.069(2) 0.040(2) 0.0056(13) -0.0061(10) -0.0118(13) C17 0.073(2) 0.095(3) 0.035(2) 0.001(2) -0.0124(14) -0.044(2) C18 0.094(3) 0.052(2) 0.042(2) -0.0083(13) 0.017(2) -0.022(2) C19 0.080(2) 0.044(2) 0.044(2) 0.0030(12) 0.0240(15) 0.0017(14) C20 0.0431(14) 0.0439(14) 0.0334(14) 0.0022(10) 0.0064(10) -0.0019(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C7 1.325(3) . ? O2 C7 1.215(3) . ? O3 C8 1.326(3) . ? O4 C8 1.222(3) . ? O5 C9 1.235(3) . ? N C9 1.340(3) . ? N C13 1.457(3) . ? C1 C7 1.518(3) . ? C1 C10 1.542(4) . ? C1 C6 1.542(3) . ? C1 C2 1.543(4) . ? C2 C3 1.535(4) . ? C3 C8 1.525(3) . ? C3 C4 1.532(3) . ? C3 C11 1.554(3) . ? C4 C5 1.539(3) . ? C5 C12 1.544(3) . ? C5 C9 1.547(3) . ? C5 C6 1.554(3) . ? C13 C14 1.530(3) . ? C14 C15 1.506(3) . ? C15 C16 1.389(3) . ? C15 C20 1.394(3) . ? C16 C17 1.407(5) . ? C17 C18 1.363(5) . ? C18 C19 1.356(5) . ? C19 C20 1.376(4) . ? 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 C9 N C13 121.0(2) . . ? C7 C1 C10 106.3(2) . . ? C7 C1 C6 112.1(2) . . ? C10 C1 C6 108.3(2) . . ? C7 C1 C2 110.9(2) . . ? C10 C1 C2 109.4(2) . . ? C6 C1 C2 109.7(2) . . ? C3 C2 C1 115.9(2) . . ? C8 C3 C4 113.9(2) . . ? C8 C3 C2 112.3(2) . . ? C4 C3 C2 110.2(2) . . ? C8 C3 C11 103.6(2) . . ? C4 C3 C11 108.1(2) . . ? C2 C3 C11 108.3(2) . . ? C3 C4 C5 117.1(2) . . ? C4 C5 C12 111.9(2) . . ? C4 C5 C9 107.5(2) . . ? C12 C5 C9 105.1(2) . . ? C4 C5 C6 110.6(2) . . ? C12 C5 C6 114.1(2) . . ? C9 C5 C6 107.3(2) . . ? C1 C6 C5 119.2(2) . . ? O2 C7 O1 120.3(2) . . ? O2 C7 C1 124.3(2) . . ? O1 C7 C1 115.3(2) . . ? O4 C8 O3 121.9(2) . . ? O4 C8 C3 125.3(2) . . ? O3 C8 C3 112.8(2) . . ? O5 C9 N 121.4(2) . . ? O5 C9 C5 122.1(2) . . ? N C9 C5 116.5(2) . . ? N C13 C14 112.8(2) . . ? C15 C14 C13 113.9(2) . . ? C16 C15 C20 117.7(2) . . ? C16 C15 C14 121.8(2) . . ? C20 C15 C14 120.4(2) . . ? C15 C16 C17 119.5(3) . . ? C18 C17 C16 120.7(3) . . ? C19 C18 C17 120.4(3) . . ? C18 C19 C20 119.8(3) . . ? C19 C20 C15 121.9(3) . . ?