# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2005 data_global _journal_coden_Cambridge 182 loop_ _publ_author_name 'Reiko Kuroda' 'Yoshitane Imai' 'Tomohiro Sato' 'Masatoshi Takeshita' _publ_contact_author_name 'ProfD Reiko Kuroda' _publ_contact_author_address ; Life Sciences, Graduate School of Arts and Sciences, The University of Tokyo, JST ERATO-SORST 3-8-1 Komaba, Meguro-ku, Tokyo 153-8902 JAPAN ; _publ_contact_author_email CKURODA@MAIL.ECC.U-TOKYO.AC.JP _publ_requested_journal 'Chemical Communications' _publ_section_title ; Efficient Optical Resolution of Secondary Alkyl Alcohols by Chiral Supramolecular Hosts ; data_316121a _database_code_depnum_ccdc_archive 'CCDC 267537' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C32 H38 N2 O6' _chemical_formula_weight 546.64 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 0.0016 '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 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 9.7328(7) _cell_length_b 13.7878(9) _cell_length_c 22.0639(14) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2960.8(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9999 _cell_measurement_theta_min 1.74 _cell_measurement_theta_max 28.34 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.226 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1168 _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9589 _exptl_absorpt_correction_T_max 0.9916 _exptl_absorpt_process_details 'Bruker SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 22219 _diffrn_reflns_av_R_equivalents 0.0402 _diffrn_reflns_av_sigmaI/netI 0.0975 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 1.74 _diffrn_reflns_theta_max 28.34 _reflns_number_total 7357 _reflns_number_gt 4670 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0381P)^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 none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.0(9) _refine_ls_number_reflns 7357 _refine_ls_number_parameters 389 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0726 _refine_ls_R_factor_gt 0.0464 _refine_ls_wR_factor_ref 0.0896 _refine_ls_wR_factor_gt 0.0849 _refine_ls_goodness_of_fit_ref 0.839 _refine_ls_restrained_S_all 0.839 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.29480(18) 0.95043(14) 0.85461(9) 0.0199(4) Uani 1 1 d . . . C2 C 0.22829(18) 0.93937(14) 0.91052(9) 0.0198(4) Uani 1 1 d . . . C3 C 0.17872(19) 1.02035(14) 0.94055(9) 0.0241(5) Uani 1 1 d . . . H3 H 0.1339 1.0126 0.9775 0.029 Uiso 1 1 calc R . . C4 C 0.1945(2) 1.11209(15) 0.91681(9) 0.0269(5) Uani 1 1 d . . . H4 H 0.1624 1.1659 0.9379 0.032 Uiso 1 1 calc R . . C5 C 0.2586(2) 1.12351(15) 0.86113(10) 0.0292(5) Uani 1 1 d . . . H5 H 0.2693 1.1850 0.8445 0.035 Uiso 1 1 calc R . . C6 C 0.3067(2) 1.04284(15) 0.83044(9) 0.0260(5) Uani 1 1 d . . . H6 H 0.3478 1.0508 0.7927 0.031 Uiso 1 1 calc R . . C7 C 0.21342(19) 0.84113(15) 0.93985(8) 0.0202(4) Uani 1 1 d . . . C10 C 0.3421(2) 0.86537(14) 0.81778(8) 0.0207(5) Uani 1 1 d . . . C11 C 0.4712(2) 0.82100(15) 0.82416(8) 0.0204(4) Uani 1 1 d . . . C12 C 0.5050(2) 0.74331(15) 0.78738(9) 0.0275(5) Uani 1 1 d . . . H12 H 0.5907 0.7142 0.7916 0.033 Uiso 1 1 calc R . . C13 C 0.4142(2) 0.70773(16) 0.74423(9) 0.0310(5) Uani 1 1 d . . . H13 H 0.4386 0.6556 0.7198 0.037 Uiso 1 1 calc R . . C14 C 0.2873(2) 0.75099(16) 0.73825(9) 0.0290(5) Uani 1 1 d . . . H14 H 0.2251 0.7274 0.7098 0.035 Uiso 1 1 calc R . . C15 C 0.2516(2) 0.82920(16) 0.77415(8) 0.0262(5) Uani 1 1 d . . . H15 H 0.1661 0.8582 0.7692 0.031 Uiso 1 1 calc R . . C16 C 0.5722(2) 0.85295(15) 0.87202(8) 0.0224(5) Uani 1 1 d . . . C21 C 0.14217(18) 0.56299(14) 0.95144(8) 0.0198(4) Uani 1 1 d . . . H21 H 0.1731 0.5952 0.9143 0.024 Uiso 1 1 calc R . . C23 C 0.07276(19) 0.46905(15) 0.93385(9) 0.0227(5) Uani 1 1 d . . . C24 C -0.0201(2) 0.42467(16) 0.97231(10) 0.0298(5) Uani 1 1 d . . . H24 H -0.0387 0.4519 1.0100 0.036 Uiso 1 1 calc R . . C25 C -0.0854(2) 0.34027(16) 0.95506(11) 0.0379(6) Uani 1 1 d . . . H25 H -0.1489 0.3114 0.9809 0.046 Uiso 1 1 calc R . . C26 C -0.0572(2) 0.29874(17) 0.90007(11) 0.0380(6) Uani 1 1 d . . . H26 H -0.1018 0.2419 0.8887 0.046 Uiso 1 1 calc R . . C27 C 0.0364(3) 0.34056(17) 0.86175(10) 0.0382(6) Uani 1 1 d . . . H27 H 0.0563 0.3116 0.8247 0.046 Uiso 1 1 calc R . . C28 C 0.1014(2) 0.42621(16) 0.87831(9) 0.0314(5) Uani 1 1 d . . . H28 H 0.1644 0.4549 0.8521 0.038 Uiso 1 1 calc R . . C29 C 0.26883(19) 0.54430(14) 0.99145(8) 0.0191(4) Uani 1 1 d . . . H29 H 0.2415 0.5019 1.0250 0.023 Uiso 1 1 calc R . . C31 C 0.37720(19) 0.49279(15) 0.95453(9) 0.0234(5) Uani 1 1 d . . . C32 C 0.4472(2) 0.54017(18) 0.90914(10) 0.0438(6) Uani 1 1 d . . . H32 H 0.4312 0.6057 0.9021 0.053 Uiso 1 1 calc R . . C33 C 0.5411(3) 0.4904(2) 0.87405(13) 0.0655(9) Uani 1 1 d . . . H33 H 0.5881 0.5225 0.8433 0.079 Uiso 1 1 calc R . . C34 C 0.5654(3) 0.3930(2) 0.88450(13) 0.0640(9) Uani 1 1 d . . . H34 H 0.6287 0.3597 0.8607 0.077 Uiso 1 1 calc R . . C35 C 0.4972(2) 0.34594(19) 0.92933(12) 0.0467(7) Uani 1 1 d . . . H35 H 0.5140 0.2805 0.9365 0.056 Uiso 1 1 calc R . . C36 C 0.4027(2) 0.39538(15) 0.96442(10) 0.0307(5) Uani 1 1 d . . . H36 H 0.3558 0.3628 0.9950 0.037 Uiso 1 1 calc R . . O8 O 0.31703(13) 0.78684(10) 0.94087(6) 0.0254(3) Uani 1 1 d . . . O9 O 0.09864(13) 0.81985(9) 0.96296(6) 0.0263(3) Uani 1 1 d . . . O17 O 0.55752(13) 0.93493(10) 0.89631(5) 0.0231(3) Uani 1 1 d . . . O18 O 0.66701(14) 0.79475(10) 0.88630(6) 0.0318(4) Uani 1 1 d . . . N22 N 0.04147(18) 0.62861(14) 0.98253(9) 0.0220(4) Uani 1 1 d . . . N30 N 0.32197(18) 0.63733(13) 1.01737(8) 0.0183(4) Uani 1 1 d . . . O41 O 0.24487(16) 0.57756(11) 0.62992(7) 0.0381(4) Uani 1 1 d . . . H41 H 0.3125 0.5427 0.6259 0.057 Uiso 1 1 calc R . . C42 C 0.1349(2) 0.52268(18) 0.65628(10) 0.0406(6) Uani 1 1 d . . . H42A H 0.1128 0.4687 0.6298 0.049 Uiso 1 1 calc R . . H42B H 0.0541 0.5635 0.6592 0.049 Uiso 1 1 calc R . . C43 C 0.1699(3) 0.48396(18) 0.71858(10) 0.0445(7) Uani 1 1 d . . . H43A H 0.1932 0.5370 0.7449 0.067 Uiso 1 1 calc R . . H43B H 0.2465 0.4404 0.7156 0.067 Uiso 1 1 calc R . . H43C H 0.0920 0.4500 0.7348 0.067 Uiso 1 1 calc R . . O46 O 0.83047(19) 0.63751(14) 0.89623(7) 0.0556(5) Uani 1 1 d . . . H46 H 0.7769 0.6834 0.8964 0.083 Uiso 1 1 calc R . . C47 C 0.8641(4) 0.6123(2) 0.83446(16) 0.0871(12) Uani 1 1 d . . . H47A H 0.9167 0.5526 0.8337 0.104 Uiso 1 1 calc R . . H47B H 0.7805 0.6023 0.8114 0.104 Uiso 1 1 calc R . . C48 C 0.9419(3) 0.6884(2) 0.8083(2) 0.1203(18) Uani 1 1 d . . . H48A H 1.0173 0.7044 0.8345 0.180 Uiso 1 1 calc R . . H48B H 0.8844 0.7444 0.8030 0.180 Uiso 1 1 calc R . . H48C H 0.9766 0.6680 0.7696 0.180 Uiso 1 1 calc R . . H22A H -0.033(2) 0.6295(15) 0.9597(9) 0.036(7) Uiso 1 1 d . . . H22C H 0.074(2) 0.6961(17) 0.9834(9) 0.039(6) Uiso 1 1 d . . . H22B H 0.031(2) 0.6096(15) 1.0249(10) 0.036(6) Uiso 1 1 d . . . H30B H 0.317(2) 0.6871(18) 0.9900(11) 0.048(8) Uiso 1 1 d . . . H30C H 0.403(2) 0.6341(15) 1.0292(9) 0.030(6) Uiso 1 1 d . . . H30A H 0.263(2) 0.6572(16) 1.0587(10) 0.044(6) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0133(10) 0.0187(11) 0.0276(10) 0.0016(9) -0.0049(8) 0.0019(9) C2 0.0112(9) 0.0191(11) 0.0292(11) 0.0025(10) -0.0022(8) 0.0012(9) C3 0.0166(10) 0.0241(12) 0.0316(11) -0.0005(10) 0.0010(9) 0.0018(9) C4 0.0222(11) 0.0178(11) 0.0408(13) -0.0034(10) -0.0008(10) 0.0042(9) C5 0.0270(12) 0.0185(12) 0.0420(13) 0.0089(11) -0.0040(11) 0.0000(10) C6 0.0202(11) 0.0263(12) 0.0315(11) 0.0054(10) -0.0016(9) 0.0029(10) C7 0.0160(10) 0.0231(11) 0.0216(10) -0.0045(9) -0.0036(8) -0.0010(9) C10 0.0195(10) 0.0217(11) 0.0207(10) 0.0054(9) 0.0014(9) -0.0026(9) C11 0.0190(10) 0.0213(11) 0.0208(10) 0.0037(9) 0.0005(8) -0.0016(9) C12 0.0223(11) 0.0309(13) 0.0292(12) -0.0011(11) -0.0037(9) 0.0054(10) C13 0.0317(12) 0.0300(13) 0.0314(12) -0.0066(10) -0.0042(10) 0.0025(11) C14 0.0251(11) 0.0373(14) 0.0245(11) -0.0013(11) -0.0081(10) -0.0029(11) C15 0.0202(11) 0.0322(13) 0.0262(11) 0.0041(10) -0.0034(9) 0.0030(10) C16 0.0171(11) 0.0257(12) 0.0244(11) 0.0046(10) -0.0001(9) 0.0018(10) C21 0.0167(10) 0.0211(11) 0.0217(10) -0.0016(9) -0.0003(8) 0.0050(9) C23 0.0172(10) 0.0224(11) 0.0286(11) -0.0010(10) -0.0078(9) 0.0074(9) C24 0.0264(11) 0.0235(12) 0.0395(13) -0.0067(11) 0.0010(10) 0.0013(10) C25 0.0313(12) 0.0211(12) 0.0613(16) -0.0056(12) 0.0016(12) -0.0010(11) C26 0.0359(14) 0.0223(13) 0.0557(16) -0.0056(12) -0.0167(13) 0.0030(11) C27 0.0505(15) 0.0321(14) 0.0320(12) -0.0078(12) -0.0189(12) 0.0081(13) C28 0.0374(13) 0.0320(13) 0.0248(11) 0.0006(11) -0.0084(10) 0.0055(12) C29 0.0191(10) 0.0172(11) 0.0211(10) 0.0028(9) 0.0006(8) 0.0003(9) C31 0.0177(10) 0.0279(12) 0.0245(11) -0.0041(10) -0.0016(9) 0.0042(9) C32 0.0451(15) 0.0392(16) 0.0471(14) 0.0041(13) 0.0182(13) 0.0097(13) C33 0.069(2) 0.063(2) 0.0647(19) -0.0006(17) 0.0449(16) 0.0112(17) C34 0.0485(18) 0.076(2) 0.0679(19) -0.0242(18) 0.0212(16) 0.0191(17) C35 0.0358(14) 0.0399(16) 0.0645(17) -0.0186(14) -0.0083(13) 0.0146(13) C36 0.0269(12) 0.0232(12) 0.0420(13) -0.0064(11) -0.0098(10) 0.0053(10) O8 0.0167(7) 0.0236(8) 0.0360(8) 0.0087(7) 0.0019(6) 0.0048(6) O9 0.0157(7) 0.0208(8) 0.0423(8) 0.0039(7) 0.0057(6) -0.0003(6) O17 0.0207(7) 0.0188(8) 0.0298(8) -0.0026(7) -0.0033(6) 0.0000(6) O18 0.0275(8) 0.0307(9) 0.0372(8) -0.0066(7) -0.0160(7) 0.0104(7) N22 0.0164(9) 0.0205(11) 0.0291(11) -0.0007(9) -0.0036(8) 0.0018(8) N30 0.0131(9) 0.0168(9) 0.0250(10) 0.0018(8) -0.0014(8) -0.0011(8) O41 0.0477(10) 0.0324(9) 0.0342(9) -0.0020(8) 0.0045(8) 0.0120(8) C42 0.0376(14) 0.0481(16) 0.0363(13) -0.0144(13) -0.0024(11) 0.0058(12) C43 0.0557(17) 0.0400(15) 0.0379(13) 0.0011(12) 0.0074(12) -0.0043(14) O46 0.0652(13) 0.0695(14) 0.0321(9) -0.0135(9) -0.0122(9) 0.0475(11) C47 0.071(2) 0.068(2) 0.122(3) -0.022(2) -0.037(2) 0.036(2) C48 0.0388(19) 0.084(3) 0.238(5) 0.094(3) 0.042(2) 0.0145(19) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C6 1.386(3) . ? C1 C2 1.401(3) . ? C1 C10 1.499(3) . ? C2 C3 1.385(3) . ? C2 C7 1.508(3) . ? C3 C4 1.378(3) . ? C4 C5 1.387(3) . ? C5 C6 1.383(3) . ? C7 O8 1.256(2) . ? C7 O9 1.263(2) . ? C10 C15 1.397(3) . ? C10 C11 1.405(3) . ? C11 C12 1.383(3) . ? C11 C16 1.508(3) . ? C12 C13 1.389(3) . ? C13 C14 1.378(3) . ? C14 C15 1.382(3) . ? C16 O17 1.259(2) . ? C16 O18 1.263(2) . ? C21 N22 1.500(2) . ? C21 C23 1.512(3) . ? C21 C29 1.538(2) . ? C23 C24 1.383(3) . ? C23 C28 1.389(3) . ? C24 C25 1.380(3) . ? C25 C26 1.369(3) . ? C26 C27 1.370(3) . ? C27 C28 1.389(3) . ? C29 N30 1.496(2) . ? C29 C31 1.510(3) . ? C31 C32 1.376(3) . ? C31 C36 1.383(3) . ? C32 C33 1.380(3) . ? C33 C34 1.383(4) . ? C34 C35 1.357(4) . ? C35 C36 1.382(3) . ? O41 C42 1.434(3) . ? C42 C43 1.513(3) . ? O46 C47 1.444(4) . ? C47 C48 1.417(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 C6 C1 C2 118.50(18) . . ? C6 C1 C10 119.01(17) . . ? C2 C1 C10 122.27(17) . . ? C3 C2 C1 119.62(18) . . ? C3 C2 C7 119.04(17) . . ? C1 C2 C7 121.31(18) . . ? C4 C3 C2 121.30(18) . . ? C3 C4 C5 119.41(19) . . ? C6 C5 C4 119.6(2) . . ? C5 C6 C1 121.50(19) . . ? O8 C7 O9 124.37(18) . . ? O8 C7 C2 117.77(17) . . ? O9 C7 C2 117.84(17) . . ? C15 C10 C11 118.53(18) . . ? C15 C10 C1 117.34(17) . . ? C11 C10 C1 124.12(17) . . ? C12 C11 C10 119.41(18) . . ? C12 C11 C16 118.82(18) . . ? C10 C11 C16 121.72(18) . . ? C11 C12 C13 121.6(2) . . ? C14 C13 C12 118.9(2) . . ? C13 C14 C15 120.5(2) . . ? C14 C15 C10 121.00(19) . . ? O17 C16 O18 123.17(18) . . ? O17 C16 C11 119.10(17) . . ? O18 C16 C11 117.72(18) . . ? N22 C21 C23 110.02(15) . . ? N22 C21 C29 111.24(15) . . ? C23 C21 C29 111.23(16) . . ? C24 C23 C28 119.0(2) . . ? C24 C23 C21 120.91(18) . . ? C28 C23 C21 120.08(19) . . ? C25 C24 C23 120.3(2) . . ? C26 C25 C24 120.3(2) . . ? C25 C26 C27 120.3(2) . . ? C26 C27 C28 119.9(2) . . ? C23 C28 C27 120.1(2) . . ? N30 C29 C31 111.59(16) . . ? N30 C29 C21 110.66(16) . . ? C31 C29 C21 109.21(14) . . ? C32 C31 C36 119.1(2) . . ? C32 C31 C29 120.99(19) . . ? C36 C31 C29 119.81(19) . . ? C31 C32 C33 120.0(2) . . ? C32 C33 C34 120.2(3) . . ? C35 C34 C33 120.1(3) . . ? C34 C35 C36 119.9(3) . . ? C35 C36 C31 120.7(2) . . ? O41 C42 C43 112.76(19) . . ? C48 C47 O46 109.1(3) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 28.34 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.592 _refine_diff_density_min -0.382 _refine_diff_density_rms 0.042 data_40204a _database_code_depnum_ccdc_archive 'CCDC 267538' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C32 H38 N2 O6' _chemical_formula_weight 546.64 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 0.0016 '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 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 11.3720(8) _cell_length_b 9.4378(7) _cell_length_c 13.8177(10) _cell_angle_alpha 90.00 _cell_angle_beta 97.694(2) _cell_angle_gamma 90.00 _cell_volume 1469.66(18) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9999 _cell_measurement_theta_min 1.49 _cell_measurement_theta_max 28.32 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.65 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.235 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 584 _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9467 _exptl_absorpt_correction_T_max 0.9873 _exptl_absorpt_process_details 'Bruker SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10974 _diffrn_reflns_av_R_equivalents 0.0186 _diffrn_reflns_av_sigmaI/netI 0.0610 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.49 _diffrn_reflns_theta_max 28.32 _reflns_number_total 6872 _reflns_number_gt 5469 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0509P)^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 none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.7(8) _refine_ls_number_reflns 6872 _refine_ls_number_parameters 391 _refine_ls_number_restraints 12 _refine_ls_R_factor_all 0.0531 _refine_ls_R_factor_gt 0.0430 _refine_ls_wR_factor_ref 0.1003 _refine_ls_wR_factor_gt 0.0981 _refine_ls_goodness_of_fit_ref 0.964 _refine_ls_restrained_S_all 0.985 _refine_ls_shift/su_max 0.037 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.80099(17) 0.1836(2) 0.73671(14) 0.0222(4) Uani 1 1 d . . . C2 C 0.69969(18) 0.2655(2) 0.70686(14) 0.0215(4) Uani 1 1 d . . . C3 C 0.6399(2) 0.3295(2) 0.77643(14) 0.0248(5) Uani 1 1 d . . . H3 H 0.5732 0.3844 0.7561 0.030 Uiso 1 1 calc R . . C4 C 0.6770(2) 0.3136(2) 0.87519(16) 0.0320(5) Uani 1 1 d . . . H4 H 0.6347 0.3550 0.9210 0.038 Uiso 1 1 calc R . . C5 C 0.7780(2) 0.2351(3) 0.90476(16) 0.0353(6) Uani 1 1 d . . . H5 H 0.8047 0.2243 0.9710 0.042 Uiso 1 1 calc R . . C6 C 0.8390(2) 0.1730(2) 0.83657(15) 0.0294(5) Uani 1 1 d . . . H6 H 0.9078 0.1223 0.8577 0.035 Uiso 1 1 calc R . . C7 C 0.64864(17) 0.2866(2) 0.60140(14) 0.0199(4) Uani 1 1 d . . . O8 O 0.65540(12) 0.18389(16) 0.54393(9) 0.0260(3) Uani 1 1 d . . . O9 O 0.60080(12) 0.40387(14) 0.57648(9) 0.0232(3) Uani 1 1 d . . . C10 C 0.87762(17) 0.1164(2) 0.66880(14) 0.0216(4) Uani 1 1 d . . . C11 C 0.84899(17) -0.0085(2) 0.61576(13) 0.0196(4) Uani 1 1 d . . . C12 C 0.92874(18) -0.0657(2) 0.55802(15) 0.0262(5) Uani 1 1 d . . . H12 H 0.9085 -0.1476 0.5222 0.031 Uiso 1 1 calc R . . C13 C 1.0376(2) -0.0024(3) 0.55336(17) 0.0342(6) Uani 1 1 d . . . H13 H 1.0904 -0.0415 0.5149 0.041 Uiso 1 1 calc R . . C14 C 1.06709(19) 0.1201(3) 0.60679(18) 0.0376(6) Uani 1 1 d . . . H14 H 1.1402 0.1634 0.6048 0.045 Uiso 1 1 calc R . . C15 C 0.98745(19) 0.1772(3) 0.66275(16) 0.0312(5) Uani 1 1 d . . . H15 H 1.0081 0.2597 0.6978 0.037 Uiso 1 1 calc R . . C16 C 0.73558(17) -0.0861(2) 0.62213(14) 0.0197(4) Uani 1 1 d . . . O17 O 0.68745(11) -0.07188(15) 0.69898(9) 0.0203(3) Uani 1 1 d . . . O18 O 0.69298(12) -0.16445(16) 0.55240(10) 0.0269(3) Uani 1 1 d . . . C21 C 0.53938(16) 0.2280(2) 0.30050(13) 0.0169(4) Uani 1 1 d . . . H21 H 0.4734 0.2466 0.2488 0.020 Uiso 1 1 calc R . . N22 N 0.49009(13) 0.17427(18) 0.38795(10) 0.0176(3) Uani 1 1 d . . . H22A H 0.4648 0.0857 0.3772 0.026 Uiso 1 1 calc R . . H22B H 0.4297 0.2288 0.3996 0.026 Uiso 1 1 calc R . . H22C H 0.5463 0.1762 0.4394 0.026 Uiso 1 1 calc R . . C23 C 0.62069(17) 0.1194(2) 0.26342(14) 0.0182(4) Uani 1 1 d . . . C24 C 0.59618(19) 0.0691(2) 0.16863(15) 0.0249(5) Uani 1 1 d . . . H24 H 0.5285 0.0996 0.1288 0.030 Uiso 1 1 calc R . . C25 C 0.6724(2) -0.0265(2) 0.13310(15) 0.0311(5) Uani 1 1 d . . . H25 H 0.6556 -0.0604 0.0695 0.037 Uiso 1 1 calc R . . C26 C 0.7728(2) -0.0714(2) 0.19182(16) 0.0309(5) Uani 1 1 d . . . H26 H 0.8241 -0.1351 0.1678 0.037 Uiso 1 1 calc R . . C27 C 0.79750(18) -0.0218(2) 0.28663(15) 0.0249(5) Uani 1 1 d . . . H27 H 0.8653 -0.0525 0.3261 0.030 Uiso 1 1 calc R . . C28 C 0.72220(17) 0.0728(2) 0.32271(14) 0.0209(4) Uani 1 1 d . . . H28 H 0.7390 0.1057 0.3865 0.025 Uiso 1 1 calc R . . C29 C 0.60879(16) 0.3678(2) 0.32388(13) 0.0161(4) Uani 1 1 d . . . H29 H 0.6849 0.3447 0.3627 0.019 Uiso 1 1 calc R . . N30 N 0.54354(14) 0.46545(17) 0.38187(11) 0.0184(4) Uani 1 1 d . . . H30A H 0.5722 0.5528 0.3785 0.028 Uiso 1 1 calc R . . H30B H 0.5524 0.4372 0.4439 0.028 Uiso 1 1 calc R . . H30C H 0.4668 0.4649 0.3581 0.028 Uiso 1 1 calc R . . C31 C 0.63377(17) 0.4399(2) 0.23068(13) 0.0194(4) Uani 1 1 d . . . C32 C 0.74667(18) 0.4371(2) 0.20330(14) 0.0243(5) Uani 1 1 d . . . H32 H 0.8075 0.3890 0.2414 0.029 Uiso 1 1 calc R . . C33 C 0.7688(2) 0.5061(3) 0.11899(15) 0.0297(5) Uani 1 1 d . . . H33 H 0.8445 0.5037 0.1007 0.036 Uiso 1 1 calc R . . C34 C 0.6789(2) 0.5783(2) 0.06183(15) 0.0292(5) Uani 1 1 d . . . H34 H 0.6940 0.6252 0.0056 0.035 Uiso 1 1 calc R . . C35 C 0.5671(2) 0.5801(2) 0.08918(14) 0.0289(5) Uani 1 1 d . . . H35 H 0.5066 0.6286 0.0508 0.035 Uiso 1 1 calc R . . C36 C 0.54271(19) 0.5115(2) 0.17237(14) 0.0232(5) Uani 1 1 d . . . H36 H 0.4664 0.5128 0.1895 0.028 Uiso 1 1 calc R . . O41 O 0.26531(16) 0.2147(3) 0.15973(17) 0.0264(6) Uani 0.829(3) 1 d P A 1 H41 H 0.2632 0.3002 0.1490 0.040 Uiso 0.829(3) 1 calc PR A 1 C42 C 0.1467(3) 0.1619(4) 0.1571(3) 0.0524(11) Uani 0.829(3) 1 d PD A 1 H42 H 0.1366 0.0844 0.1095 0.063 Uiso 0.829(3) 1 calc PR A 1 C43 C 0.1223(3) 0.0985(3) 0.2618(2) 0.0414(8) Uani 0.829(3) 1 d PD A 1 H43A H 0.1836 0.0321 0.2849 0.062 Uiso 0.829(3) 1 calc PR A 1 H43B H 0.0468 0.0514 0.2544 0.062 Uiso 0.829(3) 1 calc PR A 1 H43C H 0.1220 0.1744 0.3080 0.062 Uiso 0.829(3) 1 calc PR A 1 C44 C 0.0565(3) 0.2724(4) 0.1242(2) 0.0497(9) Uani 0.829(3) 1 d P A 1 H44A H 0.0607 0.3478 0.1721 0.060 Uiso 0.829(3) 1 calc PR A 1 H44B H -0.0223 0.2312 0.1184 0.060 Uiso 0.829(3) 1 calc PR A 1 C45 C 0.0783(3) 0.3322(4) 0.0266(2) 0.0454(9) Uani 0.829(3) 1 d P A 1 H45A H 0.1600 0.3596 0.0298 0.068 Uiso 0.829(3) 1 calc PR A 1 H45B H 0.0285 0.4134 0.0112 0.068 Uiso 0.829(3) 1 calc PR A 1 H45C H 0.0602 0.2615 -0.0231 0.068 Uiso 0.829(3) 1 calc PR A 1 O61 O 0.0708(9) 0.1982(12) 0.2041(7) 0.050 Uiso 0.171(3) 1 d PD A 2 C62 C 0.1430(14) 0.1807(16) 0.1270(10) 0.050 Uiso 0.171(3) 1 d PD A 2 H62 H 0.1456 0.0826 0.1041 0.060 Uiso 0.171(3) 1 calc PR A 2 C63 C 0.2642(11) 0.235(4) 0.1748(17) 0.050 Uiso 0.171(3) 1 d PD A 2 H63A H 0.3141 0.2531 0.1253 0.075 Uiso 0.171(3) 1 calc PR A 2 H63B H 0.3008 0.1657 0.2197 0.075 Uiso 0.171(3) 1 calc PR A 2 H63C H 0.2536 0.3217 0.2094 0.075 Uiso 0.171(3) 1 calc PR A 2 C64 C 0.0879(18) 0.2831(16) 0.0477(9) 0.050 Uiso 0.171(3) 1 d PD A 2 H64A H 0.0022 0.2824 0.0449 0.060 Uiso 0.171(3) 1 calc PR A 2 H64B H 0.1075 0.2530 -0.0154 0.060 Uiso 0.171(3) 1 calc PR A 2 C65 C 0.1352(14) 0.4340(15) 0.0702(11) 0.050 Uiso 0.171(3) 1 d PD A 2 H65A H 0.1082 0.4952 0.0162 0.075 Uiso 0.171(3) 1 calc PR A 2 H65B H 0.2204 0.4324 0.0803 0.075 Uiso 0.171(3) 1 calc PR A 2 H65C H 0.1065 0.4685 0.1280 0.075 Uiso 0.171(3) 1 calc PR A 2 O51 O 0.36196(13) 0.23198(16) 0.62798(11) 0.0280(3) Uani 1 1 d D . . H51B H 0.320(3) 0.288(3) 0.5723(17) 0.096(12) Uiso 1 1 d D . . H51A H 0.357(3) 0.282(3) 0.6905(13) 0.075(10) 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 C1 0.0251(11) 0.0133(9) 0.0257(10) -0.0006(9) -0.0055(8) -0.0059(8) C2 0.0273(11) 0.0148(10) 0.0211(11) 0.0003(8) -0.0009(8) -0.0038(8) C3 0.0326(12) 0.0182(10) 0.0232(11) -0.0013(9) 0.0022(9) -0.0042(9) C4 0.0463(15) 0.0245(12) 0.0245(11) -0.0022(9) 0.0022(10) -0.0025(10) C5 0.0499(15) 0.0313(13) 0.0204(11) -0.0022(10) -0.0113(10) -0.0055(12) C6 0.0321(12) 0.0248(11) 0.0277(11) 0.0020(10) -0.0087(9) -0.0019(10) C7 0.0189(10) 0.0192(10) 0.0210(10) 0.0011(8) 0.0002(8) -0.0015(8) O8 0.0320(8) 0.0226(8) 0.0207(7) -0.0050(6) -0.0064(6) 0.0086(6) O9 0.0303(8) 0.0178(7) 0.0209(7) 0.0008(6) 0.0010(6) 0.0039(6) C10 0.0180(10) 0.0192(10) 0.0254(10) 0.0077(9) -0.0049(8) -0.0004(8) C11 0.0163(10) 0.0196(10) 0.0217(10) 0.0058(8) -0.0016(8) 0.0008(8) C12 0.0241(11) 0.0272(12) 0.0277(11) 0.0066(10) 0.0044(8) 0.0028(9) C13 0.0229(12) 0.0416(15) 0.0397(13) 0.0123(11) 0.0094(10) 0.0048(10) C14 0.0176(11) 0.0413(15) 0.0533(15) 0.0161(12) 0.0020(10) -0.0079(10) C15 0.0266(12) 0.0260(12) 0.0382(13) 0.0063(10) -0.0059(9) -0.0084(10) C16 0.0194(10) 0.0155(10) 0.0236(10) 0.0020(8) 0.0009(8) -0.0010(8) O17 0.0207(7) 0.0192(7) 0.0211(7) -0.0011(6) 0.0036(6) -0.0030(6) O18 0.0280(8) 0.0258(8) 0.0276(8) -0.0102(7) 0.0060(6) -0.0083(7) C21 0.0180(9) 0.0166(9) 0.0157(9) 0.0009(8) 0.0002(7) 0.0016(8) N22 0.0175(8) 0.0148(8) 0.0199(8) -0.0018(7) 0.0007(6) 0.0020(7) C23 0.0182(9) 0.0143(10) 0.0227(10) -0.0012(8) 0.0047(8) -0.0016(8) C24 0.0256(11) 0.0243(11) 0.0244(10) -0.0031(9) 0.0016(8) 0.0015(9) C25 0.0390(14) 0.0316(13) 0.0236(11) -0.0090(10) 0.0077(10) 0.0025(11) C26 0.0336(12) 0.0237(12) 0.0381(13) -0.0027(10) 0.0148(10) 0.0088(10) C27 0.0217(11) 0.0244(11) 0.0298(11) 0.0039(9) 0.0070(9) 0.0046(9) C28 0.0234(10) 0.0169(10) 0.0221(10) -0.0005(8) 0.0016(8) 0.0023(8) C29 0.0146(9) 0.0163(10) 0.0174(9) 0.0002(8) 0.0019(7) 0.0015(7) N30 0.0206(9) 0.0154(8) 0.0191(8) 0.0011(6) 0.0025(6) -0.0009(7) C31 0.0258(10) 0.0149(10) 0.0175(9) -0.0037(8) 0.0034(8) -0.0025(8) C32 0.0249(11) 0.0223(11) 0.0262(11) -0.0020(9) 0.0048(8) -0.0017(9) C33 0.0315(13) 0.0317(13) 0.0290(12) -0.0043(10) 0.0153(10) -0.0061(10) C34 0.0457(14) 0.0223(12) 0.0220(11) -0.0001(9) 0.0133(10) -0.0065(10) C35 0.0424(13) 0.0247(12) 0.0188(10) 0.0000(9) 0.0014(9) 0.0052(10) C36 0.0273(12) 0.0229(11) 0.0206(10) 0.0001(9) 0.0073(8) 0.0023(9) O41 0.0152(8) 0.0323(14) 0.0327(12) -0.0175(9) 0.0067(7) -0.0035(8) C42 0.0245(16) 0.048(2) 0.085(3) -0.044(2) 0.0076(19) -0.0024(14) C43 0.0317(16) 0.0210(15) 0.068(2) 0.0005(15) -0.0062(14) 0.0032(12) C44 0.046(2) 0.054(2) 0.049(2) -0.0053(17) 0.0056(16) -0.0025(17) C45 0.048(2) 0.056(3) 0.0340(17) -0.0086(16) 0.0141(15) -0.012(2) O51 0.0348(8) 0.0237(8) 0.0266(8) 0.0026(7) 0.0083(7) 0.0076(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 C1 C6 1.393(3) . ? C1 C2 1.403(3) . ? C1 C10 1.504(3) . ? C2 C3 1.388(3) . ? C2 C7 1.508(3) . ? C3 C4 1.381(3) . ? C4 C5 1.382(3) . ? C5 C6 1.374(3) . ? C7 O9 1.261(2) . ? C7 O8 1.262(2) . ? C10 C15 1.387(3) . ? C10 C11 1.403(3) . ? C11 C12 1.395(3) . ? C11 C16 1.496(3) . ? C12 C13 1.384(3) . ? C13 C14 1.389(4) . ? C14 C15 1.377(3) . ? C16 O18 1.259(2) . ? C16 O17 1.265(2) . ? C21 N22 1.488(2) . ? C21 C23 1.515(3) . ? C21 C29 1.550(3) . ? C23 C24 1.386(3) . ? C23 C28 1.394(3) . ? C24 C25 1.386(3) . ? C25 C26 1.376(3) . ? C26 C27 1.384(3) . ? C27 C28 1.376(3) . ? C29 N30 1.483(2) . ? C29 C31 1.517(3) . ? C31 C32 1.386(3) . ? C31 C36 1.398(3) . ? C32 C33 1.386(3) . ? C33 C34 1.385(3) . ? C34 C35 1.375(3) . ? C35 C36 1.379(3) . ? O41 C42 1.433(3) . ? C42 C44 1.491(5) . ? C42 C43 1.624(4) . ? C44 C45 1.513(5) . ? O61 C62 1.439(5) . ? C62 C64 1.532(5) . ? C62 C63 1.536(5) . ? C64 C65 1.538(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 C6 C1 C2 117.67(19) . . ? C6 C1 C10 117.32(18) . . ? C2 C1 C10 124.80(17) . . ? C3 C2 C1 119.71(18) . . ? C3 C2 C7 116.79(18) . . ? C1 C2 C7 123.49(18) . . ? C4 C3 C2 121.6(2) . . ? C3 C4 C5 118.8(2) . . ? C6 C5 C4 120.1(2) . . ? C5 C6 C1 122.0(2) . . ? O9 C7 O8 124.26(18) . . ? O9 C7 C2 118.44(17) . . ? O8 C7 C2 117.29(17) . . ? C15 C10 C11 117.7(2) . . ? C15 C10 C1 117.69(19) . . ? C11 C10 C1 124.54(18) . . ? C12 C11 C10 120.09(19) . . ? C12 C11 C16 118.39(19) . . ? C10 C11 C16 121.49(17) . . ? C13 C12 C11 120.9(2) . . ? C12 C13 C14 119.3(2) . . ? C15 C14 C13 119.6(2) . . ? C14 C15 C10 122.5(2) . . ? O18 C16 O17 122.64(18) . . ? O18 C16 C11 119.28(17) . . ? O17 C16 C11 118.07(17) . . ? N22 C21 C23 110.95(15) . . ? N22 C21 C29 110.96(14) . . ? C23 C21 C29 109.27(15) . . ? C24 C23 C28 119.58(18) . . ? C24 C23 C21 119.78(17) . . ? C28 C23 C21 120.61(17) . . ? C25 C24 C23 120.1(2) . . ? C26 C25 C24 120.0(2) . . ? C25 C26 C27 120.1(2) . . ? C28 C27 C26 120.3(2) . . ? C27 C28 C23 119.87(19) . . ? N30 C29 C31 110.14(15) . . ? N30 C29 C21 111.34(14) . . ? C31 C29 C21 110.68(15) . . ? C32 C31 C36 119.58(18) . . ? C32 C31 C29 120.58(17) . . ? C36 C31 C29 119.84(17) . . ? C33 C32 C31 119.9(2) . . ? C34 C33 C32 120.5(2) . . ? C35 C34 C33 119.25(19) . . ? C34 C35 C36 121.3(2) . . ? C35 C36 C31 119.42(19) . . ? O41 C42 C44 111.8(3) . . ? O41 C42 C43 112.2(3) . . ? C44 C42 C43 109.7(2) . . ? C42 C44 C45 110.1(3) . . ? O61 C62 C64 103.8(7) . . ? O61 C62 C63 102.2(7) . . ? C64 C62 C63 110.7(7) . . ? C62 C64 C65 110.0(7) . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 28.32 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.483 _refine_diff_density_min -0.463 _refine_diff_density_rms 0.046