# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2003 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 loop_ _publ_author_name 'Jin-Gen Deng' 'Xin Cui' 'Jian Liao' 'Xiaohua Peng' 'Kai-Bei Yu' 'Juhua Zhang' _publ_contact_author_name 'Dr Jin-Gen Deng' _publ_contact_author_address ; Union Laboratory of Asymmetric Synthesis Chengdu Institute of Organic Chemistry The Chinese Academy of Sciences Chengdu 610041 CHINA ; _publ_contact_author_email JGDENG@CIOC.AC.CN _publ_section_title ; Facile resolution of racemic terbutaline and a study of molecular recognition through chiral supramolecules based on enantiodifferentiating self-assembly ; #============================================================================== data_y1077 _database_code_CSD 174434 _audit_creation_method SHELXL-97 _chemical_name_systematic ; (R)-alpha-[[(1,1-dimethylethyl)amino]methyl]-3,5-dihydroxybenzenemethanol (2S,3S)-di-O-toluoyl tartrate hydrate ; _chemical_name_common 'Crystal 7 ((R)-1/4)' _chemical_melting_point 165.8-167.0 _chemical_formula_moiety ? _chemical_formula_sum 'C32 H39 N O12' _chemical_formula_weight 629.64 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0000 '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) 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 7.917(2) _cell_length_b 19.736(5) _cell_length_c 21.320(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3331.2(14) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 28 _cell_measurement_theta_min 2.81 _cell_measurement_theta_max 11.15 _exptl_crystal_description column _exptl_crystal_colour colourless _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas calculated _exptl_crystal_density_diffrn 1.255 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1336 _exptl_absorpt_coefficient_mu 0.096 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Siemens P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 3.18 _diffrn_reflns_number 4353 _diffrn_reflns_av_R_equivalents 0.0300 _diffrn_reflns_av_sigmaI/netI 0.1433 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -1 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.91 _diffrn_reflns_theta_max 26.75 _reflns_number_total 3985 _reflns_number_gt 1598 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Siemens XSCANS' _computing_cell_refinement 'Siemens XSCANS' _computing_data_reduction 'Siemens SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Siemens SHELXTL' _computing_publication_material 'Siemens 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^)+(0.0287P)^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 0.0039(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0(10) _refine_ls_number_reflns 3985 _refine_ls_number_parameters 419 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.1520 _refine_ls_R_factor_gt 0.0495 _refine_ls_wR_factor_ref 0.0973 _refine_ls_wR_factor_gt 0.0759 _refine_ls_goodness_of_fit_ref 0.796 _refine_ls_restrained_S_all 0.796 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.4739(6) 0.69070(16) 0.82550(18) 0.0713(14) Uani 1 1 d . . . H1O H 0.4903 0.6497 0.8251 0.086 Uiso 1 1 calc R . . O2 O 0.2116(5) 0.63451(15) 1.02008(16) 0.0531(11) Uani 1 1 d . . . H2O H 0.2471 0.5969 1.0106 0.064 Uiso 1 1 calc R . . O3 O 0.3731(6) 0.90585(17) 0.9593(3) 0.113(2) Uani 1 1 d . . . H3O H 0.4528 0.8793 0.9591 0.136 Uiso 1 1 calc R . . O4 O 0.0642(4) 0.40385(15) 1.00079(15) 0.0410(9) Uani 1 1 d . . . O5 O -0.0431(5) 0.44813(16) 1.08938(16) 0.0563(11) Uani 1 1 d . . . O6 O -0.1661(5) 0.50889(19) 0.89630(18) 0.0698(13) Uani 1 1 d . . . O7 O -0.2491(5) 0.4350(2) 0.96996(17) 0.0533(10) Uani 1 1 d . . . H7O H -0.3406 0.4381 0.9521 0.064 Uiso 1 1 calc R . . O8 O 0.3721(4) 0.51630(15) 0.99113(14) 0.0443(9) Uani 1 1 d . . . O9 O 0.4588(5) 0.43158(17) 0.92916(16) 0.0509(10) Uani 1 1 d . . . O10 O 0.1515(4) 0.41376(15) 0.87870(15) 0.0430(9) Uani 1 1 d . . . O11 O 0.2939(5) 0.46668(16) 0.80198(16) 0.0614(12) Uani 1 1 d . . . N N 0.1166(5) 0.97887(17) 0.91201(16) 0.0400(11) Uani 1 1 d . . . H0A H 0.2218 0.9940 0.9198 0.048 Uiso 1 1 calc R . . H0B H 0.0565 0.9845 0.9475 0.048 Uiso 1 1 calc R . . C1 C 0.3436(7) 0.7757(2) 0.8859(2) 0.0481(15) Uani 1 1 d . . . H1 H 0.3733 0.8074 0.8555 0.058 Uiso 1 1 calc R . . C2 C 0.3862(7) 0.7078(3) 0.8783(2) 0.0473(15) Uani 1 1 d . . . C3 C 0.3462(7) 0.6608(2) 0.9226(2) 0.0419(14) Uani 1 1 d . . . H3 H 0.3799 0.6159 0.9179 0.050 Uiso 1 1 calc R . . C4 C 0.2557(7) 0.6804(2) 0.9742(2) 0.0401(14) Uani 1 1 d . . . C5 C 0.2106(7) 0.7485(2) 0.9836(2) 0.0438(14) Uani 1 1 d . . . H5 H 0.1511 0.7617 1.0191 0.053 Uiso 1 1 calc R . . C6 C 0.2572(7) 0.7954(2) 0.9386(2) 0.0463(15) Uani 1 1 d . . . C7 C 0.2227(8) 0.8701(2) 0.9516(3) 0.0527(17) Uani 1 1 d . . . H7 H 0.1564 0.8738 0.9903 0.063 Uiso 1 1 calc R . . C8 C 0.1277(7) 0.9049(2) 0.8994(2) 0.0543(17) Uani 1 1 d . . . H8A H 0.1853 0.8973 0.8599 0.065 Uiso 1 1 calc R . . H8B H 0.0149 0.8860 0.8962 0.065 Uiso 1 1 calc R . . C9 C 0.0388(8) 1.0250(3) 0.8616(3) 0.0559(17) Uani 1 1 d . . . C10 C 0.0442(7) 1.0965(2) 0.8893(2) 0.0688(19) Uani 1 1 d . . . H10A H -0.0239 1.0980 0.9266 0.103 Uiso 1 1 calc R . . H10B H 0.0011 1.1282 0.8592 0.103 Uiso 1 1 calc R . . H10C H 0.1586 1.1080 0.8996 0.103 Uiso 1 1 calc R . . C11 C -0.1423(7) 1.0033(3) 0.8517(3) 0.076(2) Uani 1 1 d . . . H11A H -0.1447 0.9584 0.8346 0.114 Uiso 1 1 calc R . . H11B H -0.1965 1.0340 0.8232 0.114 Uiso 1 1 calc R . . H11C H -0.2009 1.0038 0.8912 0.114 Uiso 1 1 calc R . . C12 C 0.1471(9) 1.0202(3) 0.8028(2) 0.089(2) Uani 1 1 d . . . H12A H 0.1408 0.9751 0.7861 0.133 Uiso 1 1 calc R . . H12B H 0.2623 1.0306 0.8131 0.133 Uiso 1 1 calc R . . H12C H 0.1067 1.0519 0.7721 0.133 Uiso 1 1 calc R . . C13 C 0.1763(8) 0.1458(2) 1.1832(2) 0.0683(19) Uani 1 1 d . . . H13A H 0.1351 0.1480 1.2255 0.102 Uiso 1 1 calc R . . H13B H 0.2959 0.1377 1.1837 0.102 Uiso 1 1 calc R . . H13C H 0.1206 0.1096 1.1614 0.102 Uiso 1 1 calc R . . C14 C 0.1403(8) 0.2127(3) 1.1501(3) 0.0532(17) Uani 1 1 d . . . C15 C 0.1840(8) 0.2240(2) 1.0890(3) 0.0631(19) Uani 1 1 d . . . H15 H 0.2391 0.1900 1.0668 0.076 Uiso 1 1 calc R . . C16 C 0.1484(8) 0.2849(2) 1.0589(2) 0.0603(19) Uani 1 1 d . . . H16 H 0.1813 0.2915 1.0174 0.072 Uiso 1 1 calc R . . C17 C 0.0641(7) 0.3355(2) 1.0907(2) 0.0410(14) Uani 1 1 d . . . C18 C 0.0191(8) 0.3246(3) 1.1531(3) 0.0621(19) Uani 1 1 d . . . H18 H -0.0365 0.3584 1.1754 0.074 Uiso 1 1 calc R . . C19 C 0.0571(8) 0.2634(3) 1.1818(3) 0.0635(18) Uani 1 1 d . . . H19 H 0.0257 0.2565 1.2234 0.076 Uiso 1 1 calc R . . C20 C 0.0222(7) 0.4011(3) 1.0619(3) 0.0471(15) Uani 1 1 d . . . C21 C 0.0379(6) 0.4670(2) 0.9675(2) 0.0378(13) Uani 1 1 d . . . H21 H 0.0532 0.5043 0.9974 0.045 Uiso 1 1 calc R . . C22 C -0.1392(7) 0.4717(3) 0.9411(3) 0.0454(15) Uani 1 1 d . . . C23 C 0.1741(7) 0.4714(2) 0.9198(2) 0.0405(14) Uani 1 1 d . . . H23 H 0.1586 0.5131 0.8954 0.049 Uiso 1 1 calc R . . C24 C 0.3510(7) 0.4720(3) 0.9487(2) 0.0394(14) Uani 1 1 d . . . C25 C 0.2230(7) 0.4172(3) 0.8206(2) 0.0462(15) Uani 1 1 d . . . C26 C 0.1894(7) 0.3543(3) 0.7836(2) 0.0462(15) Uani 1 1 d . . . C27 C 0.2588(8) 0.3517(3) 0.7240(2) 0.0550(17) Uani 1 1 d . . . H27 H 0.3309 0.3858 0.7102 0.066 Uiso 1 1 calc R . . C28 C 0.2197(8) 0.2978(3) 0.6851(2) 0.0648(19) Uani 1 1 d . . . H28 H 0.2627 0.2972 0.6445 0.078 Uiso 1 1 calc R . . C29 C 0.1192(8) 0.2452(3) 0.7047(3) 0.0609(18) Uani 1 1 d . . . C30 C 0.0557(8) 0.2484(3) 0.7651(3) 0.0652(19) Uani 1 1 d . . . H30 H -0.0117 0.2132 0.7798 0.078 Uiso 1 1 calc R . . C31 C 0.0900(8) 0.3025(3) 0.8042(3) 0.0600(18) Uani 1 1 d . . . H31 H 0.0454 0.3036 0.8445 0.072 Uiso 1 1 calc R . . C32 C 0.0765(9) 0.1857(3) 0.6621(3) 0.093(2) Uani 1 1 d . . . H32A H 0.0034 0.1549 0.6840 0.139 Uiso 1 1 calc R . . H32B H 0.1785 0.1627 0.6505 0.139 Uiso 1 1 calc R . . H32C H 0.0206 0.2020 0.6251 0.139 Uiso 1 1 calc R . . O12W O 0.5636(8) 0.5599(2) 0.8230(2) 0.0655(12) Uani 1 1 d D . . H2AW H 0.486(4) 0.534(2) 0.814(2) 0.042(19) Uiso 1 1 d D . . H2BW H 0.628(7) 0.532(3) 0.838(3) 0.15(4) Uiso 1 1 d 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 O1 0.108(4) 0.044(2) 0.062(3) 0.005(2) 0.035(3) 0.009(3) O2 0.073(3) 0.035(2) 0.051(2) 0.0064(19) 0.015(2) 0.005(2) O3 0.081(4) 0.033(2) 0.226(6) -0.004(3) -0.066(4) 0.001(3) O4 0.047(2) 0.0353(19) 0.040(2) 0.0045(17) 0.001(2) 0.0071(19) O5 0.074(3) 0.049(2) 0.046(2) -0.0065(19) 0.007(2) 0.013(2) O6 0.054(3) 0.068(3) 0.087(3) 0.033(2) -0.013(3) -0.002(2) O7 0.038(2) 0.064(2) 0.058(3) 0.003(2) -0.009(2) -0.005(2) O8 0.048(2) 0.0376(18) 0.047(2) -0.0087(18) -0.003(2) 0.0032(19) O9 0.040(2) 0.055(2) 0.058(2) -0.016(2) -0.001(2) 0.007(2) O10 0.049(2) 0.0395(19) 0.040(2) -0.0069(17) 0.000(2) -0.0020(19) O11 0.082(3) 0.050(2) 0.053(2) 0.005(2) 0.011(2) -0.016(2) N 0.045(3) 0.032(2) 0.043(2) -0.005(2) 0.000(2) 0.003(2) C1 0.066(4) 0.029(3) 0.049(3) 0.009(3) 0.006(4) -0.001(3) C2 0.055(4) 0.044(3) 0.043(3) 0.002(3) 0.007(4) -0.002(3) C3 0.057(4) 0.029(3) 0.041(3) -0.002(3) 0.007(3) -0.002(3) C4 0.040(4) 0.030(3) 0.051(3) 0.007(3) 0.005(3) -0.007(3) C5 0.054(4) 0.038(3) 0.039(3) 0.000(3) 0.010(3) -0.001(3) C6 0.049(4) 0.031(3) 0.059(4) 0.000(3) 0.000(3) 0.001(3) C7 0.070(5) 0.034(3) 0.054(4) 0.001(3) -0.001(4) 0.001(3) C8 0.067(4) 0.032(3) 0.063(4) -0.015(3) -0.006(4) 0.012(3) C9 0.073(5) 0.044(3) 0.050(4) 0.008(3) -0.017(4) 0.018(4) C10 0.082(5) 0.042(3) 0.082(5) 0.013(3) -0.011(4) 0.010(4) C11 0.069(5) 0.081(5) 0.078(5) 0.008(4) -0.034(4) 0.012(4) C12 0.124(7) 0.090(5) 0.052(4) 0.016(4) 0.014(5) 0.016(5) C13 0.075(5) 0.057(4) 0.073(4) 0.014(3) 0.001(4) 0.004(4) C14 0.059(5) 0.048(3) 0.053(4) 0.000(3) -0.018(4) -0.005(4) C15 0.100(6) 0.039(3) 0.051(4) 0.002(3) 0.007(4) 0.011(4) C16 0.099(6) 0.041(3) 0.041(3) -0.002(3) 0.009(4) 0.008(4) C17 0.043(4) 0.037(3) 0.043(3) -0.002(3) 0.000(3) 0.004(3) C18 0.086(5) 0.057(4) 0.043(4) -0.008(3) 0.012(4) 0.014(4) C19 0.082(5) 0.062(4) 0.046(4) 0.011(3) 0.005(4) 0.013(4) C20 0.046(4) 0.044(3) 0.052(4) -0.014(3) -0.002(3) 0.004(3) C21 0.035(3) 0.029(3) 0.049(3) 0.000(3) -0.003(3) 0.003(3) C22 0.039(4) 0.028(3) 0.069(4) -0.012(3) 0.012(4) 0.006(3) C23 0.047(4) 0.026(3) 0.048(3) -0.002(3) -0.001(3) 0.003(3) C24 0.038(4) 0.042(3) 0.038(3) 0.007(3) 0.000(3) -0.006(3) C25 0.046(4) 0.049(3) 0.044(3) 0.006(3) 0.002(3) 0.007(3) C26 0.050(4) 0.042(3) 0.046(4) -0.002(3) -0.004(3) 0.009(3) C27 0.067(5) 0.057(4) 0.041(3) 0.007(3) -0.007(4) 0.012(4) C28 0.088(6) 0.072(4) 0.035(4) -0.010(3) -0.009(4) 0.020(4) C29 0.067(5) 0.057(4) 0.058(4) -0.012(4) -0.014(4) 0.017(4) C30 0.075(5) 0.045(4) 0.076(5) -0.002(3) 0.003(4) -0.005(4) C31 0.071(5) 0.052(3) 0.057(4) 0.006(3) 0.003(4) 0.000(4) C32 0.115(6) 0.069(4) 0.095(5) -0.040(4) -0.032(5) 0.020(5) O12W 0.074(4) 0.043(2) 0.079(3) 0.002(2) -0.004(3) 0.000(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C2 1.366(5) . ? O1 H1O 0.8200 . ? O2 C4 1.379(5) . ? O2 H2O 0.8200 . ? O3 C7 1.394(6) . ? O3 H3O 0.8200 . ? O4 C20 1.346(5) . ? O4 C21 1.449(5) . ? O5 C20 1.213(5) . ? O6 C22 1.224(6) . ? O7 C22 1.288(6) . ? O7 H7O 0.8200 . ? O8 C24 1.269(5) . ? O9 C24 1.241(6) . ? O10 C25 1.363(5) . ? O10 C23 1.448(5) . ? O11 C25 1.195(5) . ? N C8 1.486(5) . ? N C9 1.537(6) . ? N H0A 0.9000 . ? N H0B 0.9000 . ? C1 C6 1.372(6) . ? C1 C2 1.391(6) . ? C1 H1 0.9300 . ? C2 C3 1.362(6) . ? C3 C4 1.368(6) . ? C3 H3 0.9300 . ? C4 C5 1.405(6) . ? C5 C6 1.383(6) . ? C5 H5 0.9300 . ? C6 C7 1.525(6) . ? C7 C8 1.509(6) . ? C7 H7 0.9800 . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C11 1.511(7) . ? C9 C12 1.522(7) . ? C9 C10 1.530(6) . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 C14 1.525(6) . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 C15 1.366(6) . ? C14 C19 1.376(7) . ? C15 C16 1.392(6) . ? C15 H15 0.9300 . ? C16 C17 1.380(6) . ? C16 H16 0.9300 . ? C17 C18 1.393(6) . ? C17 C20 1.470(7) . ? C18 C19 1.388(6) . ? C18 H18 0.9300 . ? C19 H19 0.9300 . ? C21 C23 1.485(6) . ? C21 C22 1.514(7) . ? C21 H21 0.9800 . ? C23 C24 1.530(6) . ? C23 H23 0.9800 . ? C25 C26 1.494(7) . ? C26 C31 1.363(7) . ? C26 C27 1.385(6) . ? C27 C28 1.383(6) . ? C27 H27 0.9300 . ? C28 C29 1.374(7) . ? C28 H28 0.9300 . ? C29 C30 1.384(7) . ? C29 C32 1.521(6) . ? C30 C31 1.382(7) . ? C30 H30 0.9300 . ? C31 H31 0.9300 . ? C32 H32A 0.9600 . ? C32 H32B 0.9600 . ? C32 H32C 0.9600 . ? O12W H2AW 0.820(10) . ? O12W H2BW 0.820(10) . ? 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 O1 H1O 109.5 . . ? C4 O2 H2O 109.5 . . ? C7 O3 H3O 109.5 . . ? C20 O4 C21 118.2(4) . . ? C22 O7 H7O 109.5 . . ? C25 O10 C23 117.4(4) . . ? C8 N C9 118.6(4) . . ? C8 N H0A 107.7 . . ? C9 N H0A 107.7 . . ? C8 N H0B 107.7 . . ? C9 N H0B 107.7 . . ? H0A N H0B 107.1 . . ? C6 C1 C2 119.2(5) . . ? C6 C1 H1 120.4 . . ? C2 C1 H1 120.4 . . ? C3 C2 O1 121.4(5) . . ? C3 C2 C1 121.4(5) . . ? O1 C2 C1 117.2(5) . . ? C2 C3 C4 119.0(5) . . ? C2 C3 H3 120.5 . . ? C4 C3 H3 120.5 . . ? C3 C4 O2 121.1(4) . . ? C3 C4 C5 121.3(5) . . ? O2 C4 C5 117.6(5) . . ? C6 C5 C4 118.2(5) . . ? C6 C5 H5 120.9 . . ? C4 C5 H5 120.9 . . ? C1 C6 C5 120.8(4) . . ? C1 C6 C7 120.9(5) . . ? C5 C6 C7 118.2(5) . . ? O3 C7 C8 106.4(4) . . ? O3 C7 C6 110.9(5) . . ? C8 C7 C6 113.3(4) . . ? O3 C7 H7 108.7 . . ? C8 C7 H7 108.7 . . ? C6 C7 H7 108.7 . . ? N C8 C7 110.1(4) . . ? N C8 H8A 109.6 . . ? C7 C8 H8A 109.6 . . ? N C8 H8B 109.6 . . ? C7 C8 H8B 109.6 . . ? H8A C8 H8B 108.2 . . ? C11 C9 C12 113.8(5) . . ? C11 C9 C10 109.9(5) . . ? C12 C9 C10 111.1(5) . . ? C11 C9 N 108.0(5) . . ? C12 C9 N 108.3(4) . . ? C10 C9 N 105.4(4) . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C9 C11 H11A 109.5 . . ? C9 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C9 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C9 C12 H12A 109.5 . . ? C9 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C9 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C14 C13 H13A 109.5 . . ? C14 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C14 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C15 C14 C19 118.2(5) . . ? C15 C14 C13 122.4(5) . . ? C19 C14 C13 119.4(5) . . ? C14 C15 C16 122.0(5) . . ? C14 C15 H15 119.0 . . ? C16 C15 H15 119.0 . . ? C17 C16 C15 119.7(5) . . ? C17 C16 H16 120.1 . . ? C15 C16 H16 120.1 . . ? C16 C17 C18 118.8(5) . . ? C16 C17 C20 122.7(5) . . ? C18 C17 C20 118.5(5) . . ? C19 C18 C17 120.0(5) . . ? C19 C18 H18 120.0 . . ? C17 C18 H18 120.0 . . ? C14 C19 C18 121.3(5) . . ? C14 C19 H19 119.4 . . ? C18 C19 H19 119.4 . . ? O5 C20 O4 122.8(5) . . ? O5 C20 C17 124.6(5) . . ? O4 C20 C17 112.6(4) . . ? O4 C21 C23 106.3(4) . . ? O4 C21 C22 111.5(4) . . ? C23 C21 C22 114.5(4) . . ? O4 C21 H21 108.1 . . ? C23 C21 H21 108.1 . . ? C22 C21 H21 108.1 . . ? O6 C22 O7 126.3(6) . . ? O6 C22 C21 119.2(5) . . ? O7 C22 C21 114.4(5) . . ? O10 C23 C21 106.2(4) . . ? O10 C23 C24 111.3(4) . . ? C21 C23 C24 113.0(4) . . ? O10 C23 H23 108.8 . . ? C21 C23 H23 108.8 . . ? C24 C23 H23 108.8 . . ? O9 C24 O8 126.2(5) . . ? O9 C24 C23 119.4(5) . . ? O8 C24 C23 114.4(5) . . ? O11 C25 O10 122.5(5) . . ? O11 C25 C26 125.9(5) . . ? O10 C25 C26 111.4(5) . . ? C31 C26 C27 119.8(5) . . ? C31 C26 C25 123.7(5) . . ? C27 C26 C25 116.5(5) . . ? C28 C27 C26 119.3(6) . . ? C28 C27 H27 120.3 . . ? C26 C27 H27 120.3 . . ? C29 C28 C27 121.9(5) . . ? C29 C28 H28 119.1 . . ? C27 C28 H28 119.1 . . ? C28 C29 C30 117.3(6) . . ? C28 C29 C32 122.0(6) . . ? C30 C29 C32 120.6(6) . . ? C31 C30 C29 121.7(6) . . ? C31 C30 H30 119.1 . . ? C29 C30 H30 119.1 . . ? C26 C31 C30 119.9(6) . . ? C26 C31 H31 120.1 . . ? C30 C31 H31 120.1 . . ? C29 C32 H32A 109.5 . . ? C29 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C29 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? H2AW O12W H2BW 98(6) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 -1.0(9) . . . . ? C6 C1 C2 O1 -179.2(5) . . . . ? O1 C2 C3 C4 -179.0(5) . . . . ? C1 C2 C3 C4 2.9(8) . . . . ? C2 C3 C4 O2 179.7(5) . . . . ? C2 C3 C4 C5 -3.0(8) . . . . ? C3 C4 C5 C6 1.3(8) . . . . ? O2 C4 C5 C6 178.6(5) . . . . ? C2 C1 C6 C5 -0.8(8) . . . . ? C2 C1 C6 C7 174.2(5) . . . . ? C4 C5 C6 C1 0.7(8) . . . . ? C4 C5 C6 C7 -174.5(5) . . . . ? C1 C6 C7 O3 -62.6(7) . . . . ? C5 C6 C7 O3 112.5(6) . . . . ? C1 C6 C7 C8 57.0(7) . . . . ? C5 C6 C7 C8 -127.9(5) . . . . ? C9 N C8 C7 174.5(5) . . . . ? O3 C7 C8 N -51.2(6) . . . . ? C6 C7 C8 N -173.4(5) . . . . ? C8 N C9 C11 61.8(6) . . . . ? C8 N C9 C12 -61.9(6) . . . . ? C8 N C9 C10 179.2(5) . . . . ? C19 C14 C15 C16 0.7(10) . . . . ? C13 C14 C15 C16 179.1(5) . . . . ? C14 C15 C16 C17 -1.1(10) . . . . ? C15 C16 C17 C18 1.1(9) . . . . ? C15 C16 C17 C20 -179.9(5) . . . . ? C16 C17 C18 C19 -0.8(9) . . . . ? C20 C17 C18 C19 -179.8(5) . . . . ? C15 C14 C19 C18 -0.4(10) . . . . ? C13 C14 C19 C18 -178.8(5) . . . . ? C17 C18 C19 C14 0.5(10) . . . . ? C21 O4 C20 O5 3.3(8) . . . . ? C21 O4 C20 C17 -176.8(4) . . . . ? C16 C17 C20 O5 -175.6(5) . . . . ? C18 C17 C20 O5 3.3(9) . . . . ? C16 C17 C20 O4 4.4(8) . . . . ? C18 C17 C20 O4 -176.7(5) . . . . ? C20 O4 C21 C23 147.3(4) . . . . ? C20 O4 C21 C22 -87.2(5) . . . . ? O4 C21 C22 O6 -156.4(4) . . . . ? C23 C21 C22 O6 -35.6(7) . . . . ? O4 C21 C22 O7 24.3(6) . . . . ? C23 C21 C22 O7 145.1(5) . . . . ? C25 O10 C23 C21 159.4(4) . . . . ? C25 O10 C23 C24 -77.3(5) . . . . ? O4 C21 C23 O10 61.4(5) . . . . ? C22 C21 C23 O10 -62.2(5) . . . . ? O4 C21 C23 C24 -60.8(5) . . . . ? C22 C21 C23 C24 175.6(4) . . . . ? O10 C23 C24 O9 9.2(6) . . . . ? C21 C23 C24 O9 128.6(5) . . . . ? O10 C23 C24 O8 -171.6(4) . . . . ? C21 C23 C24 O8 -52.3(6) . . . . ? C23 O10 C25 O11 -4.1(7) . . . . ? C23 O10 C25 C26 180.0(4) . . . . ? O11 C25 C26 C31 -171.6(6) . . . . ? O10 C25 C26 C31 4.2(7) . . . . ? O11 C25 C26 C27 5.3(8) . . . . ? O10 C25 C26 C27 -178.9(5) . . . . ? C31 C26 C27 C28 3.0(9) . . . . ? C25 C26 C27 C28 -174.1(5) . . . . ? C26 C27 C28 C29 -2.7(9) . . . . ? C27 C28 C29 C30 0.9(9) . . . . ? C27 C28 C29 C32 -179.7(5) . . . . ? C28 C29 C30 C31 0.7(9) . . . . ? C32 C29 C30 C31 -178.7(5) . . . . ? C27 C26 C31 C30 -1.5(9) . . . . ? C25 C26 C31 C30 175.3(5) . . . . ? C29 C30 C31 C26 -0.4(9) . . . . ? 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 H1O O12W 0.82 1.86 2.677(6) 170.9 . O2 H2O O8 0.82 1.92 2.727(4) 169.0 . O12W H2AW O11 0.820(10) 2.037(13) 2.854(6) 174(5) . O12W H2BW O6 0.820(10) 2.09(4) 2.835(7) 150(7) 1_655 O3 H3O O2 0.82 2.11 2.830(6) 145.8 4_567 O7 H7O O9 0.82 1.67 2.471(5) 166.3 1_455 N H0B O8 0.90 1.96 2.832(5) 162.4 4_467 N H0A O5 0.90 2.19 3.055(5) 160.3 4_567 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 26.75 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.173 _refine_diff_density_min -0.177 _refine_diff_density_rms 0.040 data_y1097 _database_code_CSD 174435 _audit_creation_method SHELXL-97 _chemical_name_systematic ; (S)-alpha-[[(1,1-dimethylethyl)amino]methyl]-3,5-dihydroxybenzenemethanol (2S,3S)-di-O-toluoyl tartrate ; _chemical_name_common 'Crystal 6((S)-1/4)' _chemical_melting_point 193.0-195.0 _chemical_formula_moiety ? _chemical_formula_sum 'C32 H37 N O11' _chemical_formula_weight 611.63 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 7.512(1) _cell_length_b 18.733(4) _cell_length_c 11.599(2) _cell_angle_alpha 90.00 _cell_angle_beta 103.10(1) _cell_angle_gamma 90.00 _cell_volume 1589.8(5) _cell_formula_units_Z 5 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 29 _cell_measurement_theta_min 3.68 _cell_measurement_theta_max 15.06 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.52 _exptl_crystal_size_mid 0.48 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas calculated _exptl_crystal_density_diffrn 1.278 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 648 _exptl_absorpt_coefficient_mu 0.097 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Siemens P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 2.20 _diffrn_reflns_number 3225 _diffrn_reflns_av_R_equivalents 0.0145 _diffrn_reflns_av_sigmaI/netI 0.0417 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.80 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2882 _reflns_number_gt 2194 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Siemens XSCANS' _computing_cell_refinement 'Siemens XSCANS' _computing_data_reduction 'Siemens SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Siemens SHELXTL' _computing_publication_material 'Siemens 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^)+(0.0666P)^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 0.014(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0(10) _refine_ls_number_reflns 2882 _refine_ls_number_parameters 407 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0579 _refine_ls_R_factor_gt 0.0418 _refine_ls_wR_factor_ref 0.1066 _refine_ls_wR_factor_gt 0.1003 _refine_ls_goodness_of_fit_ref 0.944 _refine_ls_restrained_S_all 0.943 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.9890(4) 0.5211(2) 1.1713(2) 0.0607(9) Uani 1 1 d . . . H1O H 0.9320 0.5179 1.2236 0.073 Uiso 1 1 calc R . . O2 O 0.3856(4) 0.5135(3) 0.9367(3) 0.0739(10) Uani 1 1 d . . . H2O H 0.3294 0.5056 0.8687 0.089 Uiso 1 1 calc R . . O3 O 1.0733(5) 0.47917(19) 0.7571(3) 0.0618(9) Uani 1 1 d . . . H3O H 1.0941 0.4711 0.6920 0.074 Uiso 1 1 calc R . . O4 O 0.3901(3) 0.40872(13) 0.3173(2) 0.0334(6) Uani 1 1 d . . . O5 O 0.4207(4) 0.29761(15) 0.3897(3) 0.0535(8) Uani 1 1 d . . . O6 O 0.2446(4) 0.49145(16) 0.5551(3) 0.0528(8) Uani 1 1 d . . . O7 O 0.1119(4) 0.41313(17) 0.4182(3) 0.0551(8) Uani 1 1 d . . . H7O H 0.0190 0.4252 0.4390 0.066 Uiso 1 1 calc R . . O8 O 0.7860(4) 0.52235(18) 0.3443(3) 0.0586(8) Uani 1 1 d . . . O9 O 0.8167(4) 0.43401(17) 0.4747(3) 0.0547(8) Uani 1 1 d . . . O10 O 0.4505(3) 0.55415(14) 0.3615(2) 0.0381(6) Uani 1 1 d . . . O11 O 0.6281(4) 0.63806(15) 0.4693(2) 0.0497(8) Uani 1 1 d . . . N N 0.9945(4) 0.60469(18) 0.6011(3) 0.0375(8) Uani 1 1 d . . . H0A H 0.8898 0.6050 0.5450 0.045 Uiso 1 1 calc R . . H0B H 1.0585 0.5661 0.5880 0.045 Uiso 1 1 calc R . . C1 C 0.9428(5) 0.5183(2) 0.9640(3) 0.0374(9) Uani 1 1 d . . . H1 H 1.0687 0.5205 0.9724 0.045 Uiso 1 1 calc R . . C2 C 0.8708(5) 0.5189(2) 1.0642(3) 0.0406(9) Uani 1 1 d . . . C3 C 0.6828(5) 0.5168(2) 1.0520(3) 0.0446(10) Uani 1 1 d . . . H3 H 0.6337 0.5170 1.1187 0.054 Uiso 1 1 calc R . . C4 C 0.5700(5) 0.5143(2) 0.9414(4) 0.0462(10) Uani 1 1 d . . . C5 C 0.6414(5) 0.5130(2) 0.8410(4) 0.0449(10) Uani 1 1 d . . . H5 H 0.5639 0.5112 0.7662 0.054 Uiso 1 1 calc R . . C6 C 0.8315(5) 0.5143(2) 0.8535(3) 0.0366(9) Uani 1 1 d . . . C7 C 0.9088(5) 0.5181(3) 0.7430(3) 0.0434(9) Uani 1 1 d . . . H7 H 0.8189 0.4987 0.6756 0.052 Uiso 1 1 calc R . . C8 C 0.9463(6) 0.5952(2) 0.7184(4) 0.0457(10) Uani 1 1 d . . . H8A H 0.8389 0.6236 0.7202 0.055 Uiso 1 1 calc R . . H8B H 1.0461 0.6127 0.7804 0.055 Uiso 1 1 calc R . . C9 C 1.1034(5) 0.6707(2) 0.5836(3) 0.0406(9) Uani 1 1 d . . . C10 C 1.1029(7) 0.6707(3) 0.4530(4) 0.0627(13) Uani 1 1 d . . . H10A H 1.1478 0.6257 0.4320 0.075 Uiso 1 1 calc R . . H10B H 1.1801 0.7084 0.4366 0.075 Uiso 1 1 calc R . . H10C H 0.9805 0.6780 0.4076 0.075 Uiso 1 1 calc R . . C11 C 1.0111(7) 0.7368(3) 0.6175(5) 0.0675(14) Uani 1 1 d . . . H11A H 0.8889 0.7398 0.5698 0.081 Uiso 1 1 calc R . . H11B H 1.0788 0.7783 0.6046 0.081 Uiso 1 1 calc R . . H11C H 1.0072 0.7341 0.6995 0.081 Uiso 1 1 calc R . . C12 C 1.2961(6) 0.6618(3) 0.6573(4) 0.0649(14) Uani 1 1 d . . . H12A H 1.2959 0.6667 0.7397 0.078 Uiso 1 1 calc R . . H12B H 1.3737 0.6977 0.6355 0.078 Uiso 1 1 calc R . . H12C H 1.3411 0.6154 0.6435 0.078 Uiso 1 1 calc R . . C13 C 0.1228(8) 0.2364(4) -0.1725(5) 0.089(2) Uani 1 1 d . . . H13A H 0.2204 0.2123 -0.1975 0.116 Uiso 1 1 calc R . . H13B H 0.0807 0.2757 -0.2248 0.116 Uiso 1 1 calc R . . H13C H 0.0239 0.2037 -0.1743 0.116 Uiso 1 1 calc R . . C14 C 0.1907(6) 0.2640(3) -0.0486(4) 0.0578(13) Uani 1 1 d . . . C15 C 0.1977(7) 0.3367(3) -0.0248(4) 0.0643(14) Uani 1 1 d . . . H15 H 0.1608 0.3689 -0.0866 0.077 Uiso 1 1 calc R . . C16 C 0.2588(6) 0.3621(3) 0.0897(4) 0.0523(12) Uani 1 1 d . . . H16 H 0.2622 0.4109 0.1048 0.063 Uiso 1 1 calc R . . C17 C 0.3148(5) 0.3138(2) 0.1817(3) 0.0364(9) Uani 1 1 d . . . C18 C 0.3073(6) 0.2416(2) 0.1574(4) 0.0486(11) Uani 1 1 d . . . H18 H 0.3434 0.2090 0.2188 0.058 Uiso 1 1 calc R . . C19 C 0.2467(6) 0.2171(3) 0.0429(4) 0.0605(13) Uani 1 1 d . . . H19 H 0.2439 0.1683 0.0279 0.073 Uiso 1 1 calc R . . C20 C 0.3810(5) 0.3372(2) 0.3062(3) 0.0333(9) Uani 1 1 d . . . C21 C 0.4247(5) 0.4365(2) 0.4353(3) 0.0308(8) Uani 1 1 d . . . H21 H 0.4938 0.4003 0.4882 0.037 Uiso 1 1 calc R . . C22 C 0.2462(5) 0.4495(2) 0.4741(3) 0.0361(9) Uani 1 1 d . . . C23 C 0.5442(4) 0.5014(2) 0.4419(3) 0.0316(8) Uani 1 1 d . . . H23 H 0.5654 0.5208 0.5223 0.038 Uiso 1 1 calc R . . C24 C 0.7294(5) 0.4849(2) 0.4146(3) 0.0359(9) Uani 1 1 d . . . C25 C 0.5193(5) 0.6211(2) 0.3797(4) 0.0379(9) Uani 1 1 d . . . C26 C 0.4458(5) 0.6695(2) 0.2798(4) 0.0397(9) Uani 1 1 d . . . C27 C 0.4725(7) 0.7430(2) 0.2965(4) 0.0547(12) Uani 1 1 d . . . H27 H 0.5289 0.7607 0.3707 0.066 Uiso 1 1 calc R . . C28 C 0.4146(8) 0.7895(3) 0.2021(5) 0.0645(14) Uani 1 1 d . . . H28 H 0.4320 0.8384 0.2136 0.077 Uiso 1 1 calc R . . C29 C 0.3320(7) 0.7641(3) 0.0917(5) 0.0600(13) Uani 1 1 d . . . C30 C 0.3019(7) 0.6906(3) 0.0770(4) 0.0584(13) Uani 1 1 d . . . H30 H 0.2429 0.6730 0.0033 0.070 Uiso 1 1 calc R . . C31 C 0.3580(6) 0.6440(2) 0.1697(4) 0.0495(11) Uani 1 1 d . . . H31 H 0.3368 0.5953 0.1584 0.059 Uiso 1 1 calc R . . C32 C 0.2726(9) 0.8146(4) -0.0133(6) 0.0873(18) Uani 1 1 d . . . H32A H 0.3166 0.8619 0.0092 0.113 Uiso 1 1 calc R . . H32B H 0.1416 0.8153 -0.0372 0.113 Uiso 1 1 calc R . . H32C H 0.3223 0.7985 -0.0781 0.113 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0458(17) 0.106(3) 0.0326(15) 0.0028(18) 0.0129(12) -0.0047(19) O2 0.0383(16) 0.112(3) 0.073(2) 0.006(3) 0.0144(15) -0.003(2) O3 0.081(2) 0.075(2) 0.0381(16) 0.0105(16) 0.0328(16) 0.0279(19) O4 0.0391(15) 0.0308(15) 0.0298(13) -0.0016(11) 0.0068(11) -0.0007(12) O5 0.074(2) 0.0349(16) 0.0470(18) 0.0049(14) 0.0030(15) 0.0063(15) O6 0.0409(16) 0.064(2) 0.0582(19) -0.0224(16) 0.0200(14) -0.0046(14) O7 0.0262(14) 0.0570(19) 0.084(2) -0.0201(17) 0.0173(15) -0.0038(14) O8 0.062(2) 0.062(2) 0.0634(19) 0.0119(17) 0.0397(16) 0.0080(17) O9 0.0335(15) 0.062(2) 0.073(2) 0.0179(17) 0.0208(14) 0.0085(15) O10 0.0304(14) 0.0361(15) 0.0434(16) 0.0003(12) -0.0007(12) -0.0037(12) O11 0.0493(17) 0.0485(18) 0.0474(17) -0.0146(15) 0.0031(14) -0.0064(14) N 0.0381(17) 0.0410(19) 0.0348(17) -0.0017(14) 0.0111(14) -0.0017(15) C1 0.0306(19) 0.048(2) 0.035(2) 0.0054(19) 0.0093(15) -0.0012(19) C2 0.037(2) 0.048(2) 0.037(2) 0.006(2) 0.0102(16) -0.001(2) C3 0.044(2) 0.051(2) 0.044(2) 0.003(2) 0.0223(19) 0.004(2) C4 0.029(2) 0.051(3) 0.059(3) 0.005(2) 0.0115(18) -0.001(2) C5 0.039(2) 0.053(2) 0.040(2) 0.006(2) 0.0020(17) -0.004(2) C6 0.034(2) 0.038(2) 0.038(2) 0.0051(19) 0.0085(16) -0.0028(19) C7 0.041(2) 0.056(3) 0.033(2) 0.002(2) 0.0075(16) -0.005(2) C8 0.058(3) 0.042(2) 0.044(2) -0.0008(19) 0.027(2) 0.000(2) C9 0.039(2) 0.039(2) 0.046(2) 0.0060(19) 0.0156(18) -0.0032(19) C10 0.066(3) 0.066(3) 0.063(3) 0.021(3) 0.029(2) -0.003(3) C11 0.078(3) 0.041(3) 0.090(4) 0.003(3) 0.032(3) 0.001(3) C12 0.049(3) 0.068(3) 0.073(3) 0.006(3) 0.004(2) -0.013(3) C13 0.080(4) 0.133(6) 0.059(3) -0.044(4) 0.026(3) -0.037(4) C14 0.049(3) 0.076(4) 0.052(3) -0.024(3) 0.018(2) -0.014(3) C15 0.078(3) 0.068(4) 0.044(3) -0.004(2) 0.006(2) -0.007(3) C16 0.067(3) 0.046(3) 0.041(3) -0.005(2) 0.006(2) -0.001(2) C17 0.037(2) 0.035(2) 0.039(2) -0.0068(18) 0.0125(17) -0.0021(17) C18 0.049(3) 0.036(2) 0.062(3) -0.007(2) 0.014(2) -0.003(2) C19 0.058(3) 0.054(3) 0.070(3) -0.029(3) 0.017(3) -0.005(2) C20 0.030(2) 0.030(2) 0.039(2) 0.0020(18) 0.0078(17) 0.0064(16) C21 0.0296(19) 0.037(2) 0.0248(18) 0.0010(16) 0.0052(14) 0.0028(16) C22 0.032(2) 0.038(2) 0.038(2) -0.0028(18) 0.0074(17) 0.0014(18) C23 0.0248(18) 0.038(2) 0.0297(19) -0.0003(16) 0.0019(15) 0.0031(16) C24 0.038(2) 0.040(2) 0.030(2) -0.0067(18) 0.0098(17) -0.0042(19) C25 0.031(2) 0.040(2) 0.044(2) -0.0032(18) 0.0104(18) -0.0026(18) C26 0.036(2) 0.036(2) 0.050(2) -0.0008(19) 0.0170(19) -0.0001(18) C27 0.063(3) 0.045(3) 0.057(3) -0.003(2) 0.018(2) -0.002(2) C28 0.077(3) 0.036(3) 0.085(4) 0.008(3) 0.028(3) 0.001(2) C29 0.058(3) 0.057(3) 0.071(3) 0.020(3) 0.028(3) 0.012(2) C30 0.061(3) 0.059(3) 0.052(3) 0.007(2) 0.007(2) 0.002(2) C31 0.051(3) 0.044(2) 0.052(3) 0.001(2) 0.009(2) -0.001(2) C32 0.091(4) 0.076(4) 0.099(4) 0.041(3) 0.030(4) 0.020(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C2 1.354(4) . ? O1 H1O 0.8200 . ? O2 C4 1.374(5) . ? O2 H2O 0.8200 . ? O3 C7 1.412(5) . ? O3 H3O 0.8200 . ? O4 C20 1.347(4) . ? O4 C21 1.432(4) . ? O5 C20 1.202(5) . ? O6 C22 1.228(4) . ? O7 C22 1.267(4) . ? O7 H7O 0.8200 . ? O8 C24 1.222(5) . ? O9 C24 1.272(5) . ? O10 C25 1.355(5) . ? O10 C23 1.429(4) . ? O11 C25 1.210(4) . ? N C8 1.496(5) . ? N C9 1.522(5) . ? N H0A 0.9000 . ? N H0B 0.9000 . ? C1 C6 1.365(5) . ? C1 C2 1.388(5) . ? C1 H1 0.9300 . ? C2 C3 1.387(5) . ? C3 C4 1.368(5) . ? C3 H3 0.9300 . ? C4 C5 1.388(6) . ? C5 C6 1.402(5) . ? C5 H5 0.9300 . ? C6 C7 1.524(5) . ? C7 C8 1.511(6) . ? C7 H7 0.9800 . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C11 1.512(6) . ? C9 C10 1.514(6) . ? C9 C12 1.515(6) . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 C14 1.503(6) . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 C19 1.368(7) . ? C14 C15 1.389(7) . ? C15 C16 1.388(6) . ? C15 H15 0.9300 . ? C16 C17 1.389(6) . ? C16 H16 0.9300 . ? C17 C18 1.381(6) . ? C17 C20 1.482(5) . ? C18 C19 1.381(6) . ? C18 H18 0.9300 . ? C19 H19 0.9300 . ? C21 C23 1.504(5) . ? C21 C22 1.527(5) . ? C21 H21 0.9800 . ? C23 C24 1.527(5) . ? C23 H23 0.9800 . ? C25 C26 1.476(6) . ? C26 C31 1.383(6) . ? C26 C27 1.399(6) . ? C27 C28 1.390(7) . ? C27 H27 0.9300 . ? C28 C29 1.375(7) . ? C28 H28 0.9300 . ? C29 C30 1.399(7) . ? C29 C32 1.528(7) . ? C30 C31 1.375(6) . ? C30 H30 0.9300 . ? C31 H31 0.9300 . ? C32 H32A 0.9600 . ? C32 H32B 0.9600 . ? C32 H32C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 O1 H1O 109.5 . . ? C4 O2 H2O 109.5 . . ? C7 O3 H3O 109.5 . . ? C20 O4 C21 116.6(3) . . ? C22 O7 H7O 109.5 . . ? C25 O10 C23 115.1(3) . . ? C8 N C9 117.8(3) . . ? C8 N H0A 107.9 . . ? C9 N H0A 107.9 . . ? C8 N H0B 107.9 . . ? C9 N H0B 107.9 . . ? H0A N H0B 107.2 . . ? C6 C1 C2 121.0(3) . . ? C6 C1 H1 119.5 . . ? C2 C1 H1 119.5 . . ? O1 C2 C3 122.4(3) . . ? O1 C2 C1 118.0(3) . . ? C3 C2 C1 119.7(3) . . ? C4 C3 C2 119.8(4) . . ? C4 C3 H3 120.1 . . ? C2 C3 H3 120.1 . . ? C3 C4 O2 116.2(4) . . ? C3 C4 C5 120.8(4) . . ? O2 C4 C5 123.0(4) . . ? C4 C5 C6 119.4(4) . . ? C4 C5 H5 120.3 . . ? C6 C5 H5 120.3 . . ? C1 C6 C5 119.4(4) . . ? C1 C6 C7 121.2(3) . . ? C5 C6 C7 119.2(3) . . ? O3 C7 C8 108.7(3) . . ? O3 C7 C6 111.6(3) . . ? C8 C7 C6 109.0(3) . . ? O3 C7 H7 109.2 . . ? C8 C7 H7 109.2 . . ? C6 C7 H7 109.2 . . ? N C8 C7 112.2(3) . . ? N C8 H8A 109.2 . . ? C7 C8 H8A 109.2 . . ? N C8 H8B 109.2 . . ? C7 C8 H8B 109.2 . . ? H8A C8 H8B 107.9 . . ? C11 C9 C10 111.3(4) . . ? C11 C9 C12 112.3(4) . . ? C10 C9 C12 110.5(4) . . ? C11 C9 N 109.8(3) . . ? C10 C9 N 104.7(3) . . ? C12 C9 N 108.0(3) . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C9 C11 H11A 109.5 . . ? C9 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C9 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C9 C12 H12A 109.5 . . ? C9 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C9 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C14 C13 H13A 109.5 . . ? C14 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C14 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C19 C14 C15 118.9(4) . . ? C19 C14 C13 120.0(5) . . ? C15 C14 C13 121.1(5) . . ? C16 C15 C14 121.0(5) . . ? C16 C15 H15 119.5 . . ? C14 C15 H15 119.5 . . ? C15 C16 C17 119.3(4) . . ? C15 C16 H16 120.3 . . ? C17 C16 H16 120.3 . . ? C18 C17 C16 119.3(4) . . ? C18 C17 C20 118.5(4) . . ? C16 C17 C20 122.2(4) . . ? C19 C18 C17 120.7(5) . . ? C19 C18 H18 119.7 . . ? C17 C18 H18 119.7 . . ? C14 C19 C18 120.7(5) . . ? C14 C19 H19 119.7 . . ? C18 C19 H19 119.7 . . ? O5 C20 O4 122.5(4) . . ? O5 C20 C17 124.8(4) . . ? O4 C20 C17 112.7(3) . . ? O4 C21 C23 108.6(3) . . ? O4 C21 C22 111.0(3) . . ? C23 C21 C22 114.2(3) . . ? O4 C21 H21 107.6 . . ? C23 C21 H21 107.6 . . ? C22 C21 H21 107.6 . . ? O6 C22 O7 126.2(3) . . ? O6 C22 C21 119.3(3) . . ? O7 C22 C21 114.5(3) . . ? O10 C23 C21 109.0(3) . . ? O10 C23 C24 110.0(3) . . ? C21 C23 C24 112.8(3) . . ? O10 C23 H23 108.3 . . ? C21 C23 H23 108.3 . . ? C24 C23 H23 108.3 . . ? O8 C24 O9 125.6(4) . . ? O8 C24 C23 119.6(4) . . ? O9 C24 C23 114.7(3) . . ? O11 C25 O10 122.4(4) . . ? O11 C25 C26 124.9(4) . . ? O10 C25 C26 112.6(3) . . ? C31 C26 C27 119.4(4) . . ? C31 C26 C25 121.9(4) . . ? C27 C26 C25 118.7(4) . . ? C28 C27 C26 119.9(5) . . ? C28 C27 H27 120.0 . . ? C26 C27 H27 120.0 . . ? C29 C28 C27 120.7(5) . . ? C29 C28 H28 119.6 . . ? C27 C28 H28 119.6 . . ? C28 C29 C30 118.8(5) . . ? C28 C29 C32 121.1(5) . . ? C30 C29 C32 120.1(5) . . ? C31 C30 C29 121.1(5) . . ? C31 C30 H30 119.5 . . ? C29 C30 H30 119.5 . . ? C30 C31 C26 120.1(4) . . ? C30 C31 H31 120.0 . . ? C26 C31 H31 120.0 . . ? C29 C32 H32A 109.5 . . ? C29 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C29 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 O1 178.4(4) . . . . ? C6 C1 C2 C3 -1.1(7) . . . . ? O1 C2 C3 C4 -179.7(4) . . . . ? C1 C2 C3 C4 -0.2(7) . . . . ? C2 C3 C4 O2 -178.9(4) . . . . ? C2 C3 C4 C5 0.8(7) . . . . ? C3 C4 C5 C6 -0.2(7) . . . . ? O2 C4 C5 C6 179.6(5) . . . . ? C2 C1 C6 C5 1.8(7) . . . . ? C2 C1 C6 C7 176.3(4) . . . . ? C4 C5 C6 C1 -1.2(7) . . . . ? C4 C5 C6 C7 -175.8(4) . . . . ? C1 C6 C7 O3 40.3(6) . . . . ? C5 C6 C7 O3 -145.2(4) . . . . ? C1 C6 C7 C8 -79.8(5) . . . . ? C5 C6 C7 C8 94.7(5) . . . . ? C9 N C8 C7 -157.1(3) . . . . ? O3 C7 C8 N 67.2(4) . . . . ? C6 C7 C8 N -170.9(3) . . . . ? C8 N C9 C11 -51.7(5) . . . . ? C8 N C9 C10 -171.2(4) . . . . ? C8 N C9 C12 71.1(4) . . . . ? C19 C14 C15 C16 -0.5(8) . . . . ? C13 C14 C15 C16 179.4(5) . . . . ? C14 C15 C16 C17 0.4(8) . . . . ? C15 C16 C17 C18 -0.5(7) . . . . ? C15 C16 C17 C20 -179.8(4) . . . . ? C16 C17 C18 C19 0.7(6) . . . . ? C20 C17 C18 C19 -180.0(4) . . . . ? C15 C14 C19 C18 0.7(7) . . . . ? C13 C14 C19 C18 -179.2(4) . . . . ? C17 C18 C19 C14 -0.8(7) . . . . ? C21 O4 C20 O5 -8.6(5) . . . . ? C21 O4 C20 C17 170.5(3) . . . . ? C18 C17 C20 O5 -3.9(6) . . . . ? C16 C17 C20 O5 175.4(4) . . . . ? C18 C17 C20 O4 177.0(3) . . . . ? C16 C17 C20 O4 -3.7(5) . . . . ? C20 O4 C21 C23 143.8(3) . . . . ? C20 O4 C21 C22 -89.8(4) . . . . ? O4 C21 C22 O6 -158.6(3) . . . . ? C23 C21 C22 O6 -35.4(5) . . . . ? O4 C21 C22 O7 22.8(5) . . . . ? C23 C21 C22 O7 146.0(3) . . . . ? C25 O10 C23 C21 163.6(3) . . . . ? C25 O10 C23 C24 -72.3(4) . . . . ? O4 C21 C23 O10 61.2(3) . . . . ? C22 C21 C23 O10 -63.3(4) . . . . ? O4 C21 C23 C24 -61.3(4) . . . . ? C22 C21 C23 C24 174.2(3) . . . . ? O10 C23 C24 O8 9.7(5) . . . . ? C21 C23 C24 O8 131.7(4) . . . . ? O10 C23 C24 O9 -174.1(3) . . . . ? C21 C23 C24 O9 -52.2(4) . . . . ? C23 O10 C25 O11 -13.5(5) . . . . ? C23 O10 C25 C26 167.0(3) . . . . ? O11 C25 C26 C31 164.1(4) . . . . ? O10 C25 C26 C31 -16.4(5) . . . . ? O11 C25 C26 C27 -13.4(6) . . . . ? O10 C25 C26 C27 166.1(4) . . . . ? C31 C26 C27 C28 -1.5(7) . . . . ? C25 C26 C27 C28 176.1(4) . . . . ? C26 C27 C28 C29 -0.4(7) . . . . ? C27 C28 C29 C30 2.0(8) . . . . ? C27 C28 C29 C32 -178.3(5) . . . . ? C28 C29 C30 C31 -1.9(8) . . . . ? C32 C29 C30 C31 178.5(4) . . . . ? C29 C30 C31 C26 0.0(7) . . . . ? C27 C26 C31 C30 1.7(6) . . . . ? C25 C26 C31 C30 -175.8(4) . . . . ? 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 N H0A O11 0.90 2.06 2.897(4) 154.6 . O7 H7O O9 0.82 1.67 2.482(4) 169.2 1_455 O2 H2O O3 0.82 2.12 2.836(5) 145.8 1_455 N H0B O6 0.90 2.07 2.962(4) 168.9 1_655 O3 H3O O6 0.82 2.18 2.927(4) 151.3 1_655 O1 H1O O8 0.82 1.97 2.782(4) 173.1 1_556 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.575 _refine_diff_density_min -0.136 _refine_diff_density_rms 0.037 #===END data_y1066 _database_code_CSD 174436 _audit_creation_method SHELXL-97 _chemical_name_systematic ; (S)-alpha-[[(1,1-dimethylethyl)amino]methyl]-3,5-dihydroxybenzenemethanol (2S,3S)-di-O-toluoyl tartrate ; _chemical_name_common 'Crystal 5((S)-1/4)' _chemical_melting_point 193.0-195.0 _chemical_formula_moiety ? _chemical_formula_sum 'C32 H37 N O11' _chemical_formula_weight 611.63 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 7.506(1) _cell_length_b 18.714(3) _cell_length_c 11.590(2) _cell_angle_alpha 90.00 _cell_angle_beta 103.03(1) _cell_angle_gamma 90.00 _cell_volume 1586.1(4) _cell_formula_units_Z 2 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 3.15 _cell_measurement_theta_max 14.21 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.48 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas calculated _exptl_crystal_density_diffrn 1.281 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 648 _exptl_absorpt_coefficient_mu 0.097 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Siemens P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 3.92 _diffrn_reflns_number 4378 _diffrn_reflns_av_R_equivalents 0.0145 _diffrn_reflns_av_sigmaI/netI 0.0428 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.80 _diffrn_reflns_theta_max 28.00 _reflns_number_total 3938 _reflns_number_gt 2765 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Siemens XSCANS' _computing_cell_refinement 'Siemens XSCANS' _computing_data_reduction 'Siemens SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Siemens SHELXTL' _computing_publication_material 'Siemens 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^)+(0.0689P)^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 0.012(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0(10) _refine_ls_number_reflns 3938 _refine_ls_number_parameters 407 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0676 _refine_ls_R_factor_gt 0.0450 _refine_ls_wR_factor_ref 0.1151 _refine_ls_wR_factor_gt 0.1061 _refine_ls_goodness_of_fit_ref 0.925 _refine_ls_restrained_S_all 0.925 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.9891(3) 0.52123(18) 1.17154(19) 0.0587(7) Uani 1 1 d . . . H1O H 0.9329 0.5170 1.2242 0.070 Uiso 1 1 calc R . . O2 O 0.3851(3) 0.5135(2) 0.9361(3) 0.0727(9) Uani 1 1 d . . . H2O H 0.3298 0.5032 0.8688 0.087 Uiso 1 1 calc R . . O3 O 1.0737(4) 0.47913(16) 0.7576(2) 0.0601(7) Uani 1 1 d . . . H3O H 1.0849 0.4646 0.6929 0.072 Uiso 1 1 calc R . . O4 O 0.3898(3) 0.40876(10) 0.31712(17) 0.0321(5) Uani 1 1 d . . . O5 O 0.4211(4) 0.29753(13) 0.3896(2) 0.0514(6) Uani 1 1 d . . . O6 O 0.2452(3) 0.49148(14) 0.5552(2) 0.0530(7) Uani 1 1 d . . . O7 O 0.1116(3) 0.41304(14) 0.4180(2) 0.0529(7) Uani 1 1 d . . . H7O H 0.0183 0.4258 0.4377 0.063 Uiso 1 1 calc R . . O8 O 0.7862(3) 0.52234(15) 0.3445(2) 0.0559(6) Uani 1 1 d . . . O9 O 0.8166(3) 0.43413(14) 0.4749(2) 0.0530(6) Uani 1 1 d . . . O10 O 0.4505(3) 0.55416(11) 0.36168(19) 0.0373(5) Uani 1 1 d . . . O11 O 0.6279(3) 0.63790(13) 0.4691(2) 0.0486(6) Uani 1 1 d . . . N N 0.9940(3) 0.60468(14) 0.6013(2) 0.0359(6) Uani 1 1 d . . . H0A H 0.8895 0.6051 0.5450 0.043 Uiso 1 1 calc R . . H0B H 1.0577 0.5659 0.5883 0.043 Uiso 1 1 calc R . . C1 C 0.9437(4) 0.51777(19) 0.9646(3) 0.0388(7) Uani 1 1 d . . . H1 H 1.0698 0.5192 0.9730 0.047 Uiso 1 1 calc R . . C2 C 0.8701(4) 0.5188(2) 1.0645(3) 0.0410(7) Uani 1 1 d . . . C3 C 0.6821(4) 0.5167(2) 1.0527(3) 0.0440(8) Uani 1 1 d . . . H3 H 0.6329 0.5169 1.1195 0.053 Uiso 1 1 calc R . . C4 C 0.5689(4) 0.5143(2) 0.9413(3) 0.0467(8) Uani 1 1 d . . . C5 C 0.6412(4) 0.5129(2) 0.8407(3) 0.0451(8) Uani 1 1 d . . . H5 H 0.5641 0.5108 0.7657 0.054 Uiso 1 1 calc R . . C6 C 0.8312(4) 0.51466(18) 0.8537(3) 0.0375(7) Uani 1 1 d . . . C7 C 0.9078(4) 0.51852(19) 0.7432(2) 0.0390(7) Uani 1 1 d . . . H7 H 0.8178 0.4990 0.6760 0.047 Uiso 1 1 calc R . . C8 C 0.9452(5) 0.59535(19) 0.7182(3) 0.0460(8) Uani 1 1 d . . . H8A H 0.8376 0.6237 0.7197 0.055 Uiso 1 1 calc R . . H8B H 1.0448 0.6129 0.7802 0.055 Uiso 1 1 calc R . . C9 C 1.1041(4) 0.67066(18) 0.5837(3) 0.0409(7) Uani 1 1 d . . . C10 C 1.1031(6) 0.6710(2) 0.4532(3) 0.0620(11) Uani 1 1 d . . . H10A H 1.1536 0.6270 0.4325 0.074 Uiso 1 1 calc R . . H10B H 1.1752 0.7104 0.4362 0.074 Uiso 1 1 calc R . . H10C H 0.9797 0.6760 0.4081 0.074 Uiso 1 1 calc R . . C11 C 1.0103(6) 0.7369(2) 0.6175(4) 0.0653(11) Uani 1 1 d . . . H11A H 0.8879 0.7395 0.5700 0.078 Uiso 1 1 calc R . . H11B H 1.0771 0.7786 0.6042 0.078 Uiso 1 1 calc R . . H11C H 1.0066 0.7343 0.6996 0.078 Uiso 1 1 calc R . . C12 C 1.2961(5) 0.6618(2) 0.6576(4) 0.0627(11) Uani 1 1 d . . . H12A H 1.2955 0.6677 0.7398 0.075 Uiso 1 1 calc R . . H12B H 1.3744 0.6972 0.6349 0.075 Uiso 1 1 calc R . . H12C H 1.3405 0.6150 0.6452 0.075 Uiso 1 1 calc R . . C13 C 0.1238(7) 0.2358(3) -0.1723(4) 0.0871(17) Uani 1 1 d . . . H13A H 0.2209 0.2107 -0.1962 0.113 Uiso 1 1 calc R . . H13B H 0.0845 0.2750 -0.2254 0.113 Uiso 1 1 calc R . . H13C H 0.0230 0.2039 -0.1744 0.113 Uiso 1 1 calc R . . C14 C 0.1909(5) 0.2638(2) -0.0484(4) 0.0581(11) Uani 1 1 d . . . C15 C 0.1981(6) 0.3366(2) -0.0242(3) 0.0637(11) Uani 1 1 d . . . H15 H 0.1613 0.3688 -0.0861 0.076 Uiso 1 1 calc R . . C16 C 0.2585(5) 0.3624(2) 0.0893(3) 0.0508(9) Uani 1 1 d . . . H16 H 0.2612 0.4113 0.1042 0.061 Uiso 1 1 calc R . . C17 C 0.3154(4) 0.31377(17) 0.1814(3) 0.0359(7) Uani 1 1 d . . . C18 C 0.3073(5) 0.24122(18) 0.1580(3) 0.0473(8) Uani 1 1 d . . . H18 H 0.3428 0.2087 0.2196 0.057 Uiso 1 1 calc R . . C19 C 0.2462(5) 0.2170(2) 0.0428(4) 0.0601(11) Uani 1 1 d . . . H19 H 0.2428 0.1682 0.0276 0.072 Uiso 1 1 calc R . . C20 C 0.3813(4) 0.33743(16) 0.3065(3) 0.0328(6) Uani 1 1 d . . . C21 C 0.4250(4) 0.43601(16) 0.4352(2) 0.0305(6) Uani 1 1 d . . . H21 H 0.4941 0.3997 0.4880 0.037 Uiso 1 1 calc R . . C22 C 0.2462(4) 0.44943(17) 0.4739(3) 0.0348(7) Uani 1 1 d . . . C23 C 0.5438(4) 0.50158(15) 0.4421(2) 0.0312(6) Uani 1 1 d . . . H23 H 0.5646 0.5209 0.5225 0.037 Uiso 1 1 calc R . . C24 C 0.7293(4) 0.48507(18) 0.4147(3) 0.0347(7) Uani 1 1 d . . . C25 C 0.5185(4) 0.62132(17) 0.3793(3) 0.0364(7) Uani 1 1 d . . . C26 C 0.4448(4) 0.66938(18) 0.2800(3) 0.0395(7) Uani 1 1 d . . . C27 C 0.4720(5) 0.7426(2) 0.2964(4) 0.0549(9) Uani 1 1 d . . . H27 H 0.5290 0.7602 0.3706 0.066 Uiso 1 1 calc R . . C28 C 0.4146(6) 0.7893(2) 0.2028(4) 0.0630(11) Uani 1 1 d . . . H28 H 0.4319 0.8382 0.2151 0.076 Uiso 1 1 calc R . . C29 C 0.3320(6) 0.7644(2) 0.0916(4) 0.0597(10) Uani 1 1 d . . . C30 C 0.3018(6) 0.6909(2) 0.0767(4) 0.0581(10) Uani 1 1 d . . . H30 H 0.2433 0.6732 0.0029 0.070 Uiso 1 1 calc R . . C31 C 0.3577(5) 0.6444(2) 0.1702(3) 0.0479(8) Uani 1 1 d . . . H31 H 0.3362 0.5957 0.1588 0.057 Uiso 1 1 calc R . . C32 C 0.2729(7) 0.8145(3) -0.0128(5) 0.0861(15) Uani 1 1 d . . . H32A H 0.3132 0.8621 0.0104 0.112 Uiso 1 1 calc R . . H32B H 0.1420 0.8139 -0.0382 0.112 Uiso 1 1 calc R . . H32C H 0.3260 0.7991 -0.0766 0.112 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0451(13) 0.103(2) 0.0308(11) 0.0017(14) 0.0144(10) -0.0028(15) O2 0.0345(12) 0.110(3) 0.0755(19) 0.005(2) 0.0173(12) -0.0009(16) O3 0.0804(18) 0.0718(18) 0.0363(13) 0.0094(13) 0.0305(13) 0.0265(15) O4 0.0351(11) 0.0303(11) 0.0300(10) -0.0013(8) 0.0059(9) 0.0011(9) O5 0.0715(17) 0.0374(13) 0.0425(13) 0.0047(11) 0.0065(11) 0.0069(12) O6 0.0423(13) 0.0635(16) 0.0577(15) -0.0224(13) 0.0208(11) -0.0032(12) O7 0.0275(11) 0.0568(15) 0.0772(17) -0.0195(13) 0.0176(12) -0.0064(11) O8 0.0597(15) 0.0634(16) 0.0560(14) 0.0106(13) 0.0370(12) 0.0070(13) O9 0.0309(11) 0.0625(17) 0.0692(16) 0.0166(14) 0.0186(11) 0.0095(12) O10 0.0324(11) 0.0344(11) 0.0409(12) 0.0014(9) -0.0006(9) -0.0019(9) O11 0.0482(13) 0.0459(14) 0.0478(13) -0.0115(11) 0.0026(11) -0.0063(11) N 0.0361(13) 0.0399(14) 0.0336(13) 0.0007(11) 0.0118(11) -0.0021(12) C1 0.0292(14) 0.0517(19) 0.0367(15) 0.0050(16) 0.0099(12) -0.0001(15) C2 0.0376(16) 0.0489(18) 0.0375(16) 0.0023(16) 0.0107(13) -0.0001(16) C3 0.0425(17) 0.0518(19) 0.0436(18) 0.0057(16) 0.0225(14) 0.0036(17) C4 0.0304(16) 0.050(2) 0.061(2) 0.0066(19) 0.0134(14) -0.0017(16) C5 0.0376(17) 0.053(2) 0.0417(17) 0.0082(17) 0.0024(13) -0.0014(16) C6 0.0383(16) 0.0397(16) 0.0354(15) 0.0050(14) 0.0104(12) -0.0018(15) C7 0.0383(16) 0.0490(18) 0.0289(14) 0.0016(14) 0.0058(12) -0.0063(16) C8 0.057(2) 0.047(2) 0.0413(18) 0.0009(15) 0.0279(16) -0.0020(17) C9 0.0422(17) 0.0396(17) 0.0445(17) 0.0057(15) 0.0177(14) -0.0024(15) C10 0.067(2) 0.067(3) 0.059(2) 0.021(2) 0.0296(19) 0.003(2) C11 0.080(3) 0.041(2) 0.080(3) 0.002(2) 0.029(2) 0.004(2) C12 0.045(2) 0.066(3) 0.072(3) 0.007(2) 0.0016(19) -0.0142(19) C13 0.078(3) 0.130(5) 0.058(3) -0.043(3) 0.023(2) -0.040(3) C14 0.049(2) 0.077(3) 0.051(2) -0.026(2) 0.0175(18) -0.017(2) C15 0.077(3) 0.071(3) 0.040(2) -0.0031(19) 0.0070(19) -0.005(2) C16 0.066(2) 0.0409(19) 0.0424(19) -0.0056(15) 0.0048(18) 0.0010(18) C17 0.0334(15) 0.0343(16) 0.0401(16) -0.0045(13) 0.0085(13) -0.0015(13) C18 0.049(2) 0.0362(18) 0.056(2) -0.0071(16) 0.0114(17) -0.0044(16) C19 0.061(2) 0.050(2) 0.071(3) -0.030(2) 0.017(2) -0.0072(19) C20 0.0313(15) 0.0329(16) 0.0358(16) 0.0006(13) 0.0109(13) 0.0040(13) C21 0.0296(14) 0.0343(16) 0.0273(14) -0.0024(12) 0.0062(11) 0.0031(12) C22 0.0303(15) 0.0378(16) 0.0369(16) -0.0015(14) 0.0088(12) 0.0031(13) C23 0.0271(14) 0.0348(16) 0.0301(14) -0.0035(12) 0.0032(11) 0.0007(12) C24 0.0330(15) 0.0397(16) 0.0330(15) -0.0069(13) 0.0106(13) -0.0050(14) C25 0.0321(15) 0.0372(17) 0.0425(17) -0.0061(14) 0.0135(14) -0.0026(14) C26 0.0364(16) 0.0390(18) 0.0469(18) 0.0002(15) 0.0175(14) -0.0016(14) C27 0.061(2) 0.045(2) 0.060(2) -0.0026(18) 0.0170(19) -0.0035(19) C28 0.078(3) 0.0340(19) 0.081(3) 0.0083(19) 0.027(2) 0.0011(19) C29 0.056(2) 0.056(2) 0.073(3) 0.021(2) 0.026(2) 0.0105(19) C30 0.062(2) 0.057(2) 0.052(2) 0.0111(19) 0.0073(18) 0.0006(19) C31 0.049(2) 0.0443(19) 0.049(2) 0.0030(16) 0.0090(16) 0.0005(16) C32 0.087(3) 0.080(3) 0.093(4) 0.041(3) 0.027(3) 0.014(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C2 1.357(4) . ? O1 H1O 0.8200 . ? O2 C4 1.368(4) . ? O2 H2O 0.8200 . ? O3 C7 1.424(4) . ? O3 H3O 0.8200 . ? O4 C20 1.341(4) . ? O4 C21 1.429(3) . ? O5 C20 1.202(4) . ? O6 C22 1.229(4) . ? O7 C22 1.268(4) . ? O7 H7O 0.8200 . ? O8 C24 1.219(4) . ? O9 C24 1.273(4) . ? O10 C25 1.355(4) . ? O10 C23 1.426(3) . ? O11 C25 1.211(4) . ? N C8 1.492(4) . ? N C9 1.525(4) . ? N H0A 0.9000 . ? N H0B 0.9000 . ? C1 C6 1.371(4) . ? C1 C2 1.391(4) . ? C1 H1 0.9300 . ? C2 C3 1.387(4) . ? C3 C4 1.378(5) . ? C3 H3 0.9300 . ? C4 C5 1.392(5) . ? C5 C6 1.400(4) . ? C5 H5 0.9300 . ? C6 C7 1.519(4) . ? C7 C8 1.505(5) . ? C7 H7 0.9800 . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.510(5) . ? C9 C12 1.511(5) . ? C9 C11 1.520(5) . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 C14 1.504(5) . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 C19 1.364(6) . ? C14 C15 1.389(6) . ? C15 C16 1.378(5) . ? C15 H15 0.9300 . ? C16 C17 1.394(5) . ? C16 H16 0.9300 . ? C17 C18 1.383(5) . ? C17 C20 1.489(4) . ? C18 C19 1.386(5) . ? C18 H18 0.9300 . ? C19 H19 0.9300 . ? C21 C23 1.509(4) . ? C21 C22 1.528(4) . ? C21 H21 0.9800 . ? C23 C24 1.528(4) . ? C23 H23 0.9800 . ? C25 C26 1.467(5) . ? C26 C31 1.375(5) . ? C26 C27 1.393(5) . ? C27 C28 1.384(6) . ? C27 H27 0.9300 . ? C28 C29 1.379(6) . ? C28 H28 0.9300 . ? C29 C30 1.398(6) . ? C29 C32 1.515(6) . ? C30 C31 1.380(5) . ? C30 H30 0.9300 . ? C31 H31 0.9300 . ? C32 H32A 0.9600 . ? C32 H32B 0.9600 . ? C32 H32C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 O1 H1O 109.5 . . ? C4 O2 H2O 109.5 . . ? C7 O3 H3O 109.5 . . ? C20 O4 C21 116.0(2) . . ? C22 O7 H7O 109.5 . . ? C25 O10 C23 115.4(2) . . ? C8 N C9 117.9(2) . . ? C8 N H0A 107.8 . . ? C9 N H0A 107.8 . . ? C8 N H0B 107.8 . . ? C9 N H0B 107.8 . . ? H0A N H0B 107.2 . . ? C6 C1 C2 120.3(3) . . ? C6 C1 H1 119.8 . . ? C2 C1 H1 119.8 . . ? O1 C2 C3 122.4(3) . . ? O1 C2 C1 117.3(3) . . ? C3 C2 C1 120.3(3) . . ? C4 C3 C2 119.4(3) . . ? C4 C3 H3 120.3 . . ? C2 C3 H3 120.3 . . ? O2 C4 C3 116.4(3) . . ? O2 C4 C5 122.9(3) . . ? C3 C4 C5 120.8(3) . . ? C4 C5 C6 119.3(3) . . ? C4 C5 H5 120.4 . . ? C6 C5 H5 120.4 . . ? C1 C6 C5 119.9(3) . . ? C1 C6 C7 121.2(3) . . ? C5 C6 C7 118.7(3) . . ? O3 C7 C8 108.7(3) . . ? O3 C7 C6 111.4(2) . . ? C8 C7 C6 109.3(3) . . ? O3 C7 H7 109.1 . . ? C8 C7 H7 109.1 . . ? C6 C7 H7 109.1 . . ? N C8 C7 112.4(3) . . ? N C8 H8A 109.1 . . ? C7 C8 H8A 109.1 . . ? N C8 H8B 109.1 . . ? C7 C8 H8B 109.1 . . ? H8A C8 H8B 107.9 . . ? C10 C9 C12 111.0(3) . . ? C10 C9 C11 110.9(3) . . ? C12 C9 C11 112.4(3) . . ? C10 C9 N 104.9(3) . . ? C12 C9 N 108.2(3) . . ? C11 C9 N 109.2(3) . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C9 C11 H11A 109.5 . . ? C9 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C9 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C9 C12 H12A 109.5 . . ? C9 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C9 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C14 C13 H13A 109.5 . . ? C14 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C14 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C19 C14 C15 118.8(4) . . ? C19 C14 C13 119.6(4) . . ? C15 C14 C13 121.6(5) . . ? C16 C15 C14 121.7(4) . . ? C16 C15 H15 119.1 . . ? C14 C15 H15 119.1 . . ? C15 C16 C17 118.7(4) . . ? C15 C16 H16 120.7 . . ? C17 C16 H16 120.7 . . ? C18 C17 C16 119.9(3) . . ? C18 C17 C20 118.2(3) . . ? C16 C17 C20 121.9(3) . . ? C17 C18 C19 120.0(4) . . ? C17 C18 H18 120.0 . . ? C19 C18 H18 120.0 . . ? C14 C19 C18 120.9(4) . . ? C14 C19 H19 119.5 . . ? C18 C19 H19 119.5 . . ? O5 C20 O4 123.1(3) . . ? O5 C20 C17 124.3(3) . . ? O4 C20 C17 112.6(3) . . ? O4 C21 C23 108.7(2) . . ? O4 C21 C22 110.8(2) . . ? C23 C21 C22 113.5(2) . . ? O4 C21 H21 107.9 . . ? C23 C21 H21 107.9 . . ? C22 C21 H21 107.9 . . ? O6 C22 O7 126.4(3) . . ? O6 C22 C21 119.2(3) . . ? O7 C22 C21 114.4(2) . . ? O10 C23 C21 109.2(2) . . ? O10 C23 C24 109.9(2) . . ? C21 C23 C24 112.4(2) . . ? O10 C23 H23 108.4 . . ? C21 C23 H23 108.4 . . ? C24 C23 H23 108.4 . . ? O8 C24 O9 125.4(3) . . ? O8 C24 C23 119.7(3) . . ? O9 C24 C23 114.7(3) . . ? O11 C25 O10 121.8(3) . . ? O11 C25 C26 125.4(3) . . ? O10 C25 C26 112.8(3) . . ? C31 C26 C27 119.1(3) . . ? C31 C26 C25 122.3(3) . . ? C27 C26 C25 118.6(3) . . ? C28 C27 C26 120.3(4) . . ? C28 C27 H27 119.9 . . ? C26 C27 H27 119.9 . . ? C29 C28 C27 120.9(4) . . ? C29 C28 H28 119.5 . . ? C27 C28 H28 119.5 . . ? C28 C29 C30 118.3(4) . . ? C28 C29 C32 121.7(4) . . ? C30 C29 C32 119.9(5) . . ? C31 C30 C29 120.8(4) . . ? C31 C30 H30 119.6 . . ? C29 C30 H30 119.6 . . ? C26 C31 C30 120.6(4) . . ? C26 C31 H31 119.7 . . ? C30 C31 H31 119.7 . . ? C29 C32 H32A 109.5 . . ? C29 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C29 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 O1 179.4(3) . . . . ? C6 C1 C2 C3 -0.1(6) . . . . ? O1 C2 C3 C4 179.9(3) . . . . ? C1 C2 C3 C4 -0.6(6) . . . . ? C2 C3 C4 O2 -179.0(4) . . . . ? C2 C3 C4 C5 1.0(6) . . . . ? O2 C4 C5 C6 179.3(4) . . . . ? C3 C4 C5 C6 -0.7(6) . . . . ? C2 C1 C6 C5 0.4(5) . . . . ? C2 C1 C6 C7 175.9(3) . . . . ? C4 C5 C6 C1 0.0(6) . . . . ? C4 C5 C6 C7 -175.6(3) . . . . ? C1 C6 C7 O3 39.6(5) . . . . ? C5 C6 C7 O3 -144.8(3) . . . . ? C1 C6 C7 C8 -80.5(4) . . . . ? C5 C6 C7 C8 95.1(4) . . . . ? C9 N C8 C7 -156.8(3) . . . . ? O3 C7 C8 N 66.9(3) . . . . ? C6 C7 C8 N -171.3(3) . . . . ? C8 N C9 C10 -170.7(3) . . . . ? C8 N C9 C12 70.8(4) . . . . ? C8 N C9 C11 -51.8(4) . . . . ? C19 C14 C15 C16 -0.3(7) . . . . ? C13 C14 C15 C16 179.6(4) . . . . ? C14 C15 C16 C17 0.7(6) . . . . ? C15 C16 C17 C18 -1.2(5) . . . . ? C15 C16 C17 C20 -179.6(3) . . . . ? C16 C17 C18 C19 1.3(5) . . . . ? C20 C17 C18 C19 179.8(3) . . . . ? C15 C14 C19 C18 0.5(6) . . . . ? C13 C14 C19 C18 -179.4(4) . . . . ? C17 C18 C19 C14 -1.0(6) . . . . ? C21 O4 C20 O5 -8.4(4) . . . . ? C21 O4 C20 C17 170.9(2) . . . . ? C18 C17 C20 O5 -3.2(5) . . . . ? C16 C17 C20 O5 175.3(3) . . . . ? C18 C17 C20 O4 177.5(3) . . . . ? C16 C17 C20 O4 -4.0(4) . . . . ? C20 O4 C21 C23 144.1(2) . . . . ? C20 O4 C21 C22 -90.6(3) . . . . ? O4 C21 C22 O6 -158.3(3) . . . . ? C23 C21 C22 O6 -35.8(4) . . . . ? O4 C21 C22 O7 23.4(4) . . . . ? C23 C21 C22 O7 146.0(3) . . . . ? C25 O10 C23 C21 163.9(2) . . . . ? C25 O10 C23 C24 -72.4(3) . . . . ? O4 C21 C23 O10 60.4(3) . . . . ? C22 C21 C23 O10 -63.4(3) . . . . ? O4 C21 C23 C24 -61.9(3) . . . . ? C22 C21 C23 C24 174.4(2) . . . . ? O10 C23 C24 O8 9.8(4) . . . . ? C21 C23 C24 O8 131.6(3) . . . . ? O10 C23 C24 O9 -174.1(2) . . . . ? C21 C23 C24 O9 -52.2(3) . . . . ? C23 O10 C25 O11 -13.0(4) . . . . ? C23 O10 C25 C26 167.2(2) . . . . ? O11 C25 C26 C31 163.7(3) . . . . ? O10 C25 C26 C31 -16.6(4) . . . . ? O11 C25 C26 C27 -13.2(5) . . . . ? O10 C25 C26 C27 166.5(3) . . . . ? C31 C26 C27 C28 -1.0(6) . . . . ? C25 C26 C27 C28 176.0(3) . . . . ? C26 C27 C28 C29 -0.9(6) . . . . ? C27 C28 C29 C30 2.2(6) . . . . ? C27 C28 C29 C32 -178.3(4) . . . . ? C28 C29 C30 C31 -1.7(6) . . . . ? C32 C29 C30 C31 178.8(4) . . . . ? C27 C26 C31 C30 1.6(5) . . . . ? C25 C26 C31 C30 -175.4(3) . . . . ? C29 C30 C31 C26 -0.2(6) . . . . ? 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 N H0A O11 0.90 2.06 2.896(4) 154.9 . O7 H7O O9 0.82 1.67 2.480(3) 168.2 1_455 O2 H2O O3 0.82 2.11 2.825(4) 146.0 1_455 N H0B O6 0.90 2.08 2.963(4) 168.3 1_655 O3 H3O O6 0.82 2.26 2.928(3) 138.8 1_655 O1 H1O O8 0.82 1.96 2.778(3) 171.1 1_556 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 28.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.592 _refine_diff_density_min -0.163 _refine_diff_density_rms 0.040 #===END #===END data_y1003 _database_code_CSD 174437 _audit_creation_method SHELXL-97 _chemical_name_systematic ; Inclusion complex of (R)-alpha-[[(1,1-dimethylethyl)amino]methyl]- 3,5-dihydroxybenzenemethanol (2S,3S)-di-O-toluoyl tartrate hydrate and acetone ; _chemical_name_common 'Crystal 8 ((R)-1/4)' _chemical_melting_point 165.8-167.0 _chemical_formula_moiety ? _chemical_formula_sum 'C35 H45 N O13' _chemical_formula_weight 687.72 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0000 '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) 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 7.810(1) _cell_length_b 21.431(4) _cell_length_c 21.948(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3673.6(10) _cell_formula_units_Z 4 _cell_measurement_temperature 291(2) _cell_measurement_reflns_used 28 _cell_measurement_theta_min 2.77 _cell_measurement_theta_max 12.47 _exptl_crystal_description column _exptl_crystal_colour colourless _exptl_crystal_size_max 0.58 _exptl_crystal_size_mid 0.52 _exptl_crystal_size_min 0.32 _exptl_crystal_density_meas calculated _exptl_crystal_density_diffrn 1.243 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1464 _exptl_absorpt_coefficient_mu 0.095 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 291(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Siemens P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 4.46 _diffrn_reflns_number 4670 _diffrn_reflns_av_R_equivalents 0.0163 _diffrn_reflns_av_sigmaI/netI 0.0667 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -1 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.86 _diffrn_reflns_theta_max 26.50 _reflns_number_total 4288 _reflns_number_gt 2430 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Siemens XSCANS' _computing_cell_refinement 'Siemens XSCANS' _computing_data_reduction 'Siemens SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Siemens SHELXTL' _computing_publication_material 'Siemens 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^)+(0.0595P)^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 0.0076(7) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0(10) _refine_ls_number_reflns 4288 _refine_ls_number_parameters 470 _refine_ls_number_restraints 7 _refine_ls_R_factor_all 0.0912 _refine_ls_R_factor_gt 0.0464 _refine_ls_wR_factor_ref 0.1124 _refine_ls_wR_factor_gt 0.0990 _refine_ls_goodness_of_fit_ref 0.862 _refine_ls_restrained_S_all 0.865 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.0879(5) 0.88453(13) 0.63304(13) 0.0625(9) Uani 1 1 d . . . H1 H 0.0646 0.8660 0.6647 0.075 Uiso 1 1 calc R . . O2 O 0.3318(4) 0.68579(11) 0.58353(11) 0.0501(7) Uani 1 1 d . . . H2 H 0.2897 0.6767 0.6166 0.060 Uiso 1 1 calc R . . O3 O 0.1695(5) 0.86452(18) 0.40052(15) 0.0836(12) Uani 1 1 d . . . H3 H 0.0895 0.8475 0.4181 0.100 Uiso 1 1 calc R . . O4 O 0.9924(3) 0.90950(10) 0.22974(10) 0.0358(6) Uani 1 1 d . . . O5 O 1.1043(4) 0.96788(12) 0.30476(12) 0.0537(8) Uani 1 1 d . . . O6 O 1.2368(4) 0.77443(12) 0.26303(14) 0.0608(9) Uani 1 1 d . . . O7 O 1.3101(3) 0.87009(12) 0.23447(15) 0.0540(8) Uani 1 1 d . . . H7 H 1.4022 0.8536 0.2265 0.065 Uiso 1 1 calc R . . O8 O 0.6800(3) 0.84758(11) 0.31109(10) 0.0398(6) Uani 1 1 d . . . O9 O 0.6064(3) 0.83449(13) 0.21354(12) 0.0493(7) Uani 1 1 d . . . O10 O 0.9135(3) 0.79988(11) 0.17894(10) 0.0374(6) Uani 1 1 d . . . O11 O 0.7872(4) 0.70616(12) 0.18058(12) 0.0585(8) Uani 1 1 d . . . N N 0.4419(5) 0.93218(15) 0.36393(14) 0.0379(8) Uani 1 1 d D . . C1 C 0.2074(6) 0.86659(18) 0.53653(17) 0.0489(11) Uani 1 1 d . . . H1' H 0.1789 0.9072 0.5255 0.059 Uiso 1 1 calc R . . C2 C 0.1673(6) 0.84486(17) 0.59389(17) 0.0435(10) Uani 1 1 d . . . C3 C 0.2068(5) 0.78410(17) 0.60965(16) 0.0386(9) Uani 1 1 d . . . H3' H 0.1774 0.7689 0.6479 0.046 Uiso 1 1 calc R . . C4 C 0.2891(5) 0.74645(16) 0.56881(16) 0.0377(9) Uani 1 1 d . . . C5 C 0.3324(5) 0.76785(16) 0.51155(15) 0.0382(9) Uani 1 1 d . . . H5 H 0.3895 0.7420 0.4842 0.046 Uiso 1 1 calc R . . C6 C 0.2897(6) 0.82816(17) 0.49546(15) 0.0411(10) Uani 1 1 d . . . C7 C 0.3235(6) 0.85057(18) 0.43090(15) 0.0445(10) Uani 1 1 d . . . H7' H 0.3840 0.8178 0.4084 0.053 Uiso 1 1 calc R . . C8 C 0.4282(6) 0.90976(18) 0.42887(15) 0.0453(10) Uani 1 1 d . . . H8A H 0.3742 0.9416 0.4537 0.054 Uiso 1 1 calc R . . H8B H 0.5417 0.9019 0.4451 0.054 Uiso 1 1 calc R . . C9 C 0.5261(6) 0.99564(17) 0.35259(19) 0.0468(10) Uani 1 1 d . . . C10 C 0.5361(7) 1.0028(2) 0.28371(19) 0.0636(13) Uani 1 1 d . . . H10A H 0.5875 1.0422 0.2739 0.076 Uiso 1 1 calc R . . H10B H 0.4229 1.0010 0.2668 0.076 Uiso 1 1 calc R . . H10C H 0.6042 0.9696 0.2670 0.076 Uiso 1 1 calc R . . C11 C 0.4131(7) 1.04637(18) 0.3800(2) 0.0680(14) Uani 1 1 d . . . H11A H 0.4075 1.0410 0.4234 0.082 Uiso 1 1 calc R . . H11B H 0.3001 1.0435 0.3631 0.082 Uiso 1 1 calc R . . H11C H 0.4608 1.0866 0.3708 0.082 Uiso 1 1 calc R . . C12 C 0.7014(6) 0.9953(2) 0.3814(2) 0.0750(15) Uani 1 1 d . . . H12A H 0.7617 1.0326 0.3701 0.090 Uiso 1 1 calc R . . H12B H 0.7640 0.9595 0.3675 0.090 Uiso 1 1 calc R . . H12C H 0.6900 0.9936 0.4249 0.090 Uiso 1 1 calc R . . C13 C 0.8193(7) 1.1744(2) 0.1110(2) 0.0762(16) Uani 1 1 d . . . H13A H 0.8567 1.2126 0.1298 0.091 Uiso 1 1 calc R . . H13B H 0.6966 1.1741 0.1086 0.091 Uiso 1 1 calc R . . H13C H 0.8668 1.1715 0.0708 0.091 Uiso 1 1 calc R . . C14 C 0.8788(6) 1.1198(2) 0.1486(2) 0.0566(12) Uani 1 1 d . . . C15 C 0.8629(9) 1.0604(2) 0.1268(2) 0.088(2) Uani 1 1 d . . . H15 H 0.8162 1.0539 0.0883 0.105 Uiso 1 1 calc R . . C16 C 0.9153(8) 1.0101(2) 0.1611(2) 0.0818(18) Uani 1 1 d . . . H16 H 0.9028 0.9701 0.1453 0.098 Uiso 1 1 calc R . . C17 C 0.9844(5) 1.01720(16) 0.21717(17) 0.0402(9) Uani 1 1 d . . . C18 C 1.0035(7) 1.07743(17) 0.2384(2) 0.0591(12) Uani 1 1 d . . . H18 H 1.0543 1.0842 0.2762 0.071 Uiso 1 1 calc R . . C19 C 0.9488(7) 1.12729(19) 0.2046(2) 0.0685(14) Uani 1 1 d . . . H19 H 0.9599 1.1673 0.2206 0.082 Uiso 1 1 calc R . . C20 C 1.0342(5) 0.96436(16) 0.25580(17) 0.0368(9) Uani 1 1 d . . . C21 C 1.0254(4) 0.85312(14) 0.26312(16) 0.0309(8) Uani 1 1 d . . . H21 H 1.0105 0.8617 0.3067 0.037 Uiso 1 1 calc R . . C22 C 1.2042(5) 0.82839(17) 0.25295(16) 0.0357(9) Uani 1 1 d . . . C23 C 0.8898(5) 0.80770(16) 0.24336(15) 0.0326(8) Uani 1 1 d . . . H23 H 0.9072 0.7677 0.2640 0.039 Uiso 1 1 calc R . . C24 C 0.7096(5) 0.83176(15) 0.25643(17) 0.0339(9) Uani 1 1 d . . . C25 C 0.8427(5) 0.74989(18) 0.15233(18) 0.0419(10) Uani 1 1 d . . . C26 C 0.8447(6) 0.75606(19) 0.08525(18) 0.0466(11) Uani 1 1 d . . . C27 C 0.8139(8) 0.7044(2) 0.0493(2) 0.0793(17) Uani 1 1 d . . . H27 H 0.7940 0.6658 0.0674 0.095 Uiso 1 1 calc R . . C28 C 0.8128(9) 0.7099(3) -0.0134(2) 0.095(2) Uani 1 1 d . . . H28 H 0.7954 0.6744 -0.0370 0.114 Uiso 1 1 calc R . . C29 C 0.8361(7) 0.7652(3) -0.0414(2) 0.0779(16) Uani 1 1 d . . . C30 C 0.8617(9) 0.8164(3) -0.0056(2) 0.093(2) Uani 1 1 d . . . H30 H 0.8754 0.8552 -0.0239 0.111 Uiso 1 1 calc R . . C31 C 0.8678(8) 0.8120(2) 0.05701(19) 0.0765(16) Uani 1 1 d . . . H31 H 0.8879 0.8476 0.0802 0.092 Uiso 1 1 calc R . . C32 C 0.8323(10) 0.7690(3) -0.1109(2) 0.118(3) Uani 1 1 d . . . H32A H 0.9471 0.7670 -0.1263 0.142 Uiso 1 1 calc R . . H32B H 0.7803 0.8076 -0.1231 0.142 Uiso 1 1 calc R . . H32C H 0.7671 0.7347 -0.1268 0.142 Uiso 1 1 calc R . . O12 O 0.0016(5) 0.82329(16) 0.73969(16) 0.0654(9) Uani 1 1 d D . . C33 C 0.096(2) 1.0451(5) 0.6153(3) 0.260(9) Uani 1 1 d D . . H33A H 0.0764 1.0044 0.6321 0.312 Uiso 1 1 calc R . . H33B H -0.0030 1.0707 0.6217 0.312 Uiso 1 1 calc R . . H33C H 0.1933 1.0637 0.6350 0.312 Uiso 1 1 calc R . . C34 C 0.1292(12) 1.0398(3) 0.5504(3) 0.140(3) Uani 1 1 d D . . C35 C -0.0083(16) 1.0363(6) 0.5060(5) 0.273(8) Uani 1 1 d D . . H35A H 0.0381 1.0407 0.4657 0.327 Uiso 1 1 calc R . . H35B H -0.0890 1.0692 0.5134 0.327 Uiso 1 1 calc R . . H35C H -0.0651 0.9967 0.5094 0.327 Uiso 1 1 calc R . . O13 O 0.2716(13) 1.0391(4) 0.5295(4) 0.251(5) Uani 1 1 d D . . H0A H 0.506(5) 0.9066(16) 0.3436(17) 0.071(16) Uiso 1 1 d D . . H0B H 0.340(2) 0.9351(19) 0.3492(18) 0.058(14) Uiso 1 1 d D . . H12D H -0.079(6) 0.799(2) 0.740(3) 0.13(3) Uiso 1 1 d D . . H12E H 0.072(6) 0.806(3) 0.762(2) 0.13(3) Uiso 1 1 d 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 O1 0.091(2) 0.0497(17) 0.0471(18) 0.0027(13) 0.0218(18) 0.0164(18) O2 0.066(2) 0.0467(15) 0.0378(15) 0.0110(13) 0.0095(15) 0.0125(15) O3 0.072(2) 0.122(3) 0.057(2) 0.0496(19) -0.026(2) -0.045(2) O4 0.0427(15) 0.0292(12) 0.0355(13) 0.0040(11) -0.0069(13) 0.0016(12) O5 0.070(2) 0.0430(15) 0.0484(16) -0.0003(13) -0.0160(17) -0.0022(16) O6 0.0463(17) 0.0430(16) 0.093(2) 0.0211(16) 0.0040(18) 0.0140(14) O7 0.0325(15) 0.0464(15) 0.083(2) 0.0048(16) 0.0108(17) 0.0052(14) O8 0.0429(15) 0.0463(14) 0.0302(13) -0.0007(11) 0.0043(13) 0.0083(13) O9 0.0342(15) 0.0739(19) 0.0400(15) -0.0068(14) -0.0059(14) 0.0071(15) O10 0.0394(15) 0.0414(14) 0.0315(13) -0.0061(12) 0.0081(13) -0.0022(13) O11 0.080(2) 0.0432(16) 0.0525(17) -0.0007(14) -0.0004(18) -0.0116(17) N 0.040(2) 0.0387(19) 0.0352(18) -0.0023(15) 0.0026(18) -0.0039(17) C1 0.069(3) 0.038(2) 0.039(2) 0.0058(18) 0.006(2) 0.006(2) C2 0.049(3) 0.041(2) 0.040(2) -0.0006(18) 0.003(2) 0.003(2) C3 0.045(2) 0.042(2) 0.0288(19) 0.0049(17) 0.002(2) 0.002(2) C4 0.040(2) 0.036(2) 0.037(2) 0.0035(17) -0.005(2) 0.0001(19) C5 0.041(2) 0.045(2) 0.028(2) -0.0040(16) -0.0023(18) -0.001(2) C6 0.052(3) 0.041(2) 0.0307(19) 0.0046(17) -0.006(2) -0.007(2) C7 0.060(3) 0.045(2) 0.0286(19) 0.0040(17) 0.000(2) -0.005(2) C8 0.055(3) 0.055(2) 0.0262(18) 0.0004(18) -0.0019(19) -0.012(2) C9 0.051(3) 0.036(2) 0.054(2) -0.0007(19) 0.010(2) -0.010(2) C10 0.073(3) 0.051(3) 0.066(3) 0.011(2) 0.015(3) -0.012(3) C11 0.086(4) 0.042(2) 0.076(3) -0.007(2) -0.004(3) -0.004(3) C12 0.059(3) 0.079(3) 0.086(4) -0.006(3) 0.000(3) -0.026(3) C13 0.076(4) 0.061(3) 0.091(4) 0.041(3) 0.008(3) 0.007(3) C14 0.061(3) 0.044(3) 0.065(3) 0.018(2) 0.004(3) 0.004(2) C15 0.144(6) 0.056(3) 0.064(3) 0.012(3) -0.046(4) 0.008(4) C16 0.143(5) 0.036(2) 0.067(3) 0.000(2) -0.031(4) 0.008(3) C17 0.041(2) 0.034(2) 0.046(2) 0.0069(17) -0.003(2) 0.002(2) C18 0.074(3) 0.041(2) 0.062(3) 0.002(2) -0.018(3) -0.005(2) C19 0.085(4) 0.030(2) 0.091(4) 0.010(2) -0.010(3) 0.001(2) C20 0.035(2) 0.0358(19) 0.040(2) -0.0002(18) 0.000(2) -0.0017(18) C21 0.033(2) 0.0296(18) 0.0303(18) 0.0028(15) -0.0013(17) 0.0015(17) C22 0.036(2) 0.037(2) 0.034(2) 0.0010(17) -0.0024(18) -0.0004(19) C23 0.035(2) 0.0350(19) 0.0278(18) -0.0011(16) 0.0028(17) 0.0019(17) C24 0.036(2) 0.0293(19) 0.036(2) 0.0023(16) 0.006(2) -0.0030(17) C25 0.041(2) 0.040(2) 0.044(2) -0.007(2) 0.005(2) 0.000(2) C26 0.048(3) 0.052(3) 0.039(2) -0.010(2) 0.006(2) -0.010(2) C27 0.117(5) 0.065(3) 0.056(3) -0.020(2) 0.005(3) -0.026(3) C28 0.130(6) 0.101(4) 0.055(3) -0.030(3) 0.013(4) -0.031(4) C29 0.070(4) 0.119(5) 0.044(3) -0.008(3) 0.008(3) -0.031(3) C30 0.143(6) 0.098(4) 0.038(3) 0.009(3) 0.002(3) -0.032(4) C31 0.114(5) 0.071(3) 0.045(3) -0.003(2) -0.002(3) -0.018(3) C32 0.128(6) 0.186(7) 0.041(3) 0.000(4) -0.007(4) -0.049(6) O12 0.067(2) 0.072(2) 0.057(2) 0.0121(18) -0.001(2) -0.009(2) C33 0.49(3) 0.191(9) 0.102(6) -0.041(6) 0.071(12) -0.038(13) C34 0.128(8) 0.069(4) 0.222(11) 0.009(6) 0.013(8) 0.011(5) C35 0.33(2) 0.230(12) 0.256(14) 0.063(10) -0.171(15) -0.081(14) O13 0.294(12) 0.169(6) 0.289(9) 0.025(6) 0.146(10) 0.034(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 O1 C2 1.359(4) . ? O1 H1 0.8200 . ? O2 C4 1.380(4) . ? O2 H2 0.8200 . ? O3 C7 1.407(5) . ? O3 H3 0.8200 . ? O4 C20 1.348(4) . ? O4 C21 1.436(4) . ? O5 C20 1.208(4) . ? O6 C22 1.205(4) . ? O7 C22 1.284(4) . ? O7 H7 0.8200 . ? O8 C24 1.268(4) . ? O9 C24 1.241(4) . ? O10 C25 1.339(4) . ? O10 C23 1.436(4) . ? O11 C25 1.204(4) . ? N C8 1.508(4) . ? N C9 1.531(5) . ? N H0A 0.866(10) . ? N H0B 0.865(10) . ? C1 C2 1.378(5) . ? C1 C6 1.380(5) . ? C1 H1 0.9300 . ? C2 C3 1.382(5) . ? C3 C4 1.367(5) . ? C3 H3 0.9300 . ? C4 C5 1.380(5) . ? C5 C6 1.381(5) . ? C5 H5 0.9300 . ? C6 C7 1.519(5) . ? C7 C8 1.510(5) . ? C7 H7 0.9800 . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C12 1.508(7) . ? C9 C10 1.521(5) . ? C9 C11 1.524(6) . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 C14 1.505(6) . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 C19 1.356(6) . ? C14 C15 1.365(6) . ? C15 C16 1.379(6) . ? C15 H15 0.9300 . ? C16 C17 1.352(6) . ? C16 H16 0.9300 . ? C17 C18 1.381(5) . ? C17 C20 1.467(5) . ? C18 C19 1.369(5) . ? C18 H18 0.9300 . ? C19 H19 0.9300 . ? C21 C23 1.502(5) . ? C21 C22 1.511(5) . ? C21 H21 0.9800 . ? C23 C24 1.526(5) . ? C23 H23 0.9800 . ? C25 C26 1.478(5) . ? C26 C31 1.362(6) . ? C26 C27 1.380(6) . ? C27 C28 1.383(7) . ? C27 H27 0.9300 . ? C28 C29 1.348(7) . ? C28 H28 0.9300 . ? C29 C30 1.364(7) . ? C29 C32 1.526(7) . ? C30 C31 1.379(6) . ? C30 H30 0.9300 . ? C31 H31 0.9300 . ? C32 H32A 0.9600 . ? C32 H32B 0.9600 . ? C32 H32C 0.9600 . ? O12 H12D 0.820(11) . ? O12 H12E 0.821(11) . ? C33 C34 1.452(4) . ? C33 H33A 0.9600 . ? C33 H33B 0.9600 . ? C33 H33C 0.9600 . ? C34 O13 1.203(4) . ? C34 C35 1.453(4) . ? C35 H35A 0.9600 . ? C35 H35B 0.9600 . ? C35 H35C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 O1 H1 109.5 . . ? C4 O2 H2 109.5 . . ? C7 O3 H3 109.5 . . ? C20 O4 C21 118.3(2) . . ? C22 O7 H7 109.5 . . ? C25 O10 C23 118.0(3) . . ? C8 N C9 117.8(3) . . ? C8 N H0A 109(3) . . ? C9 N H0A 103(3) . . ? C8 N H0B 108(3) . . ? C9 N H0B 106(3) . . ? H0A N H0B 113(4) . . ? C2 C1 C6 120.0(4) . . ? C2 C1 H1 120.0 . . ? C6 C1 H1 120.0 . . ? O1 C2 C1 118.0(3) . . ? O1 C2 C3 122.2(3) . . ? C1 C2 C3 119.8(4) . . ? C4 C3 C2 119.8(3) . . ? C4 C3 H3 120.1 . . ? C2 C3 H3 120.1 . . ? C3 C4 C5 121.1(3) . . ? C3 C4 O2 121.1(3) . . ? C5 C4 O2 117.8(3) . . ? C4 C5 C6 119.0(3) . . ? C4 C5 H5 120.5 . . ? C6 C5 H5 120.5 . . ? C1 C6 C5 120.3(3) . . ? C1 C6 C7 120.1(3) . . ? C5 C6 C7 119.5(3) . . ? O3 C7 C8 105.7(3) . . ? O3 C7 C6 111.2(4) . . ? C8 C7 C6 112.8(3) . . ? O3 C7 H7 109.0 . . ? C8 C7 H7 109.0 . . ? C6 C7 H7 109.0 . . ? N C8 C7 109.5(3) . . ? N C8 H8A 109.8 . . ? C7 C8 H8A 109.8 . . ? N C8 H8B 109.8 . . ? C7 C8 H8B 109.8 . . ? H8A C8 H8B 108.2 . . ? C12 C9 C10 111.7(4) . . ? C12 C9 C11 111.3(4) . . ? C10 C9 C11 110.5(4) . . ? C12 C9 N 108.5(4) . . ? C10 C9 N 105.8(3) . . ? C11 C9 N 108.7(3) . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C9 C11 H11A 109.5 . . ? C9 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C9 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C9 C12 H12A 109.5 . . ? C9 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C9 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C14 C13 H13A 109.5 . . ? C14 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C14 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C19 C14 C15 117.7(4) . . ? C19 C14 C13 122.0(4) . . ? C15 C14 C13 120.3(5) . . ? C14 C15 C16 120.8(4) . . ? C14 C15 H15 119.6 . . ? C16 C15 H15 119.6 . . ? C17 C16 C15 121.8(4) . . ? C17 C16 H16 119.1 . . ? C15 C16 H16 119.1 . . ? C16 C17 C18 117.2(4) . . ? C16 C17 C20 123.0(4) . . ? C18 C17 C20 119.8(4) . . ? C19 C18 C17 120.8(4) . . ? C19 C18 H18 119.6 . . ? C17 C18 H18 119.6 . . ? C14 C19 C18 121.7(4) . . ? C14 C19 H19 119.1 . . ? C18 C19 H19 119.1 . . ? O5 C20 O4 122.8(3) . . ? O5 C20 C17 125.9(3) . . ? O4 C20 C17 111.3(3) . . ? O4 C21 C23 105.8(3) . . ? O4 C21 C22 112.7(3) . . ? C23 C21 C22 112.4(3) . . ? O4 C21 H21 108.6 . . ? C23 C21 H21 108.6 . . ? C22 C21 H21 108.6 . . ? O6 C22 O7 126.2(4) . . ? O6 C22 C21 120.3(3) . . ? O7 C22 C21 113.5(3) . . ? O10 C23 C21 105.6(3) . . ? O10 C23 C24 110.1(3) . . ? C21 C23 C24 112.1(3) . . ? O10 C23 H23 109.6 . . ? C21 C23 H23 109.6 . . ? C24 C23 H23 109.6 . . ? O9 C24 O8 125.9(4) . . ? O9 C24 C23 118.2(3) . . ? O8 C24 C23 115.9(3) . . ? O11 C25 O10 123.1(4) . . ? O11 C25 C26 125.9(4) . . ? O10 C25 C26 111.0(3) . . ? C31 C26 C27 118.0(4) . . ? C31 C26 C25 122.2(4) . . ? C27 C26 C25 119.7(4) . . ? C26 C27 C28 120.1(5) . . ? C26 C27 H27 120.0 . . ? C28 C27 H27 120.0 . . ? C29 C28 C27 121.9(5) . . ? C29 C28 H28 119.0 . . ? C27 C28 H28 119.0 . . ? C28 C29 C30 117.7(5) . . ? C28 C29 C32 119.9(5) . . ? C30 C29 C32 122.4(6) . . ? C29 C30 C31 121.6(5) . . ? C29 C30 H30 119.2 . . ? C31 C30 H30 119.2 . . ? C26 C31 C30 120.6(5) . . ? C26 C31 H31 119.7 . . ? C30 C31 H31 119.7 . . ? C29 C32 H32A 109.5 . . ? C29 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C29 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? H12D O12 H12E 103(6) . . ? C34 C33 H33A 109.5 . . ? C34 C33 H33B 109.5 . . ? H33A C33 H33B 109.5 . . ? C34 C33 H33C 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? O13 C34 C33 122.7(11) . . ? O13 C34 C35 115.3(10) . . ? C33 C34 C35 122.1(10) . . ? C34 C35 H35A 109.5 . . ? C34 C35 H35B 109.5 . . ? H35A C35 H35B 109.5 . . ? C34 C35 H35C 109.5 . . ? H35A C35 H35C 109.5 . . ? H35B C35 H35C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 O1 179.3(4) . . . . ? C6 C1 C2 C3 -1.3(7) . . . . ? O1 C2 C3 C4 -179.0(4) . . . . ? C1 C2 C3 C4 1.6(6) . . . . ? C2 C3 C4 C5 -0.6(6) . . . . ? C2 C3 C4 O2 179.3(4) . . . . ? C3 C4 C5 C6 -0.7(6) . . . . ? O2 C4 C5 C6 179.4(4) . . . . ? C2 C1 C6 C5 0.0(7) . . . . ? C2 C1 C6 C7 176.0(4) . . . . ? C4 C5 C6 C1 1.0(6) . . . . ? C4 C5 C6 C7 -175.0(4) . . . . ? C1 C6 C7 O3 -60.6(5) . . . . ? C5 C6 C7 O3 115.5(4) . . . . ? C1 C6 C7 C8 57.9(6) . . . . ? C5 C6 C7 C8 -126.1(4) . . . . ? C9 N C8 C7 173.3(4) . . . . ? O3 C7 C8 N -53.0(4) . . . . ? C6 C7 C8 N -174.7(4) . . . . ? C8 N C9 C12 54.9(5) . . . . ? C8 N C9 C10 175.0(4) . . . . ? C8 N C9 C11 -66.3(5) . . . . ? C19 C14 C15 C16 0.5(9) . . . . ? C13 C14 C15 C16 -179.3(6) . . . . ? C14 C15 C16 C17 -0.2(10) . . . . ? C15 C16 C17 C18 -1.2(8) . . . . ? C15 C16 C17 C20 177.2(5) . . . . ? C16 C17 C18 C19 2.3(7) . . . . ? C20 C17 C18 C19 -176.2(5) . . . . ? C15 C14 C19 C18 0.6(8) . . . . ? C13 C14 C19 C18 -179.6(5) . . . . ? C17 C18 C19 C14 -2.0(8) . . . . ? C21 O4 C20 O5 3.1(5) . . . . ? C21 O4 C20 C17 -177.1(3) . . . . ? C16 C17 C20 O5 176.0(5) . . . . ? C18 C17 C20 O5 -5.7(6) . . . . ? C16 C17 C20 O4 -3.9(6) . . . . ? C18 C17 C20 O4 174.5(4) . . . . ? C20 O4 C21 C23 149.5(3) . . . . ? C20 O4 C21 C22 -87.3(4) . . . . ? O4 C21 C22 O6 -159.2(3) . . . . ? C23 C21 C22 O6 -39.8(5) . . . . ? O4 C21 C22 O7 21.9(4) . . . . ? C23 C21 C22 O7 141.4(3) . . . . ? C25 O10 C23 C21 162.0(3) . . . . ? C25 O10 C23 C24 -76.8(4) . . . . ? O4 C21 C23 O10 60.7(3) . . . . ? C22 C21 C23 O10 -62.7(4) . . . . ? O4 C21 C23 C24 -59.2(3) . . . . ? C22 C21 C23 C24 177.4(3) . . . . ? O10 C23 C24 O9 7.7(4) . . . . ? C21 C23 C24 O9 125.0(3) . . . . ? O10 C23 C24 O8 -171.9(3) . . . . ? C21 C23 C24 O8 -54.6(4) . . . . ? C23 O10 C25 O11 -13.5(6) . . . . ? C23 O10 C25 C26 167.1(3) . . . . ? O11 C25 C26 C31 162.8(5) . . . . ? O10 C25 C26 C31 -17.8(6) . . . . ? O11 C25 C26 C27 -14.0(7) . . . . ? O10 C25 C26 C27 165.4(4) . . . . ? C31 C26 C27 C28 2.0(8) . . . . ? C25 C26 C27 C28 179.0(5) . . . . ? C26 C27 C28 C29 -2.0(10) . . . . ? C27 C28 C29 C30 0.2(10) . . . . ? C27 C28 C29 C32 -179.5(6) . . . . ? C28 C29 C30 C31 1.5(10) . . . . ? C32 C29 C30 C31 -178.8(6) . . . . ? C27 C26 C31 C30 -0.4(8) . . . . ? C25 C26 C31 C30 -177.3(5) . . . . ? C29 C30 C31 C26 -1.4(10) . . . . ? 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 N H0A O8 0.866(10) 1.989(14) 2.844(4) 169(4) . O1 H1 O12 0.82 1.95 2.767(4) 178.1 . N H0B O5 0.865(10) 2.195(16) 3.037(5) 164(4) 1_455 O7 H7 O9 0.82 1.67 2.479(4) 168.3 1_655 O2 H2 O8 0.82 1.88 2.695(3) 175.4 4_466 O3 H3 O2 0.82 2.14 2.871(5) 149.2 4_466 O12 H12E O11 0.821(11) 2.12(2) 2.905(5) 160(6) 4_466 O12 H12D O6 0.820(11) 2.130(15) 2.944(5) 172(7) 4_366 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 26.50 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.238 _refine_diff_density_min -0.250 _refine_diff_density_rms 0.038 #===END