# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2006 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Reiko Kuroda' _publ_contact_author_address ; Department of Lifes Sciences The University of Tokyo Graduate School of Arts and Science Komaba Meguro-ku Tokyo 153-8901 JAPAN ; _publ_contact_author_email CKURODA@MAIL.ECC.U-TOKYO.AC.JP _publ_section_title ; Successive optical resolution of two compounds by one enantiopure compound ; loop_ _publ_author_name 'Reiko Kuroda' 'Yoshitane Imai' 'Tomohiro Sato' 'Masatoshi Takeshita' data_imai5_1 _database_code_depnum_ccdc_archive 'CCDC 287388' #data_4655a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C36 H32 N2 O5' _chemical_formula_weight 572.64 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 11.0468(8) _cell_length_b 27.344(2) _cell_length_c 9.9797(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3014.5(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9999 _cell_measurement_theta_min 1.49 _cell_measurement_theta_max 27.90 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.262 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1208 _exptl_absorpt_coefficient_mu 0.084 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9670 _exptl_absorpt_correction_T_max 0.9751 _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 'Bruker APEX' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18966 _diffrn_reflns_av_R_equivalents 0.0287 _diffrn_reflns_av_sigmaI/netI 0.0374 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -35 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.49 _diffrn_reflns_theta_max 27.90 _reflns_number_total 6985 _reflns_number_gt 6590 _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^)+(0.0759P)^2^+1.5614P] 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 -0.4(12) _refine_ls_number_reflns 6985 _refine_ls_number_parameters 396 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0647 _refine_ls_R_factor_gt 0.0612 _refine_ls_wR_factor_ref 0.1566 _refine_ls_wR_factor_gt 0.1538 _refine_ls_goodness_of_fit_ref 1.119 _refine_ls_restrained_S_all 1.119 _refine_ls_shift/su_max 0.035 _refine_ls_shift/su_mean 0.003 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 0.00626(19) 0.09612(8) 1.0288(2) 0.0151(4) Uani 1 1 d . . . C2 C -0.0115(2) 0.13455(8) 1.1166(2) 0.0180(4) Uani 1 1 d . . . C3 C 0.0269(2) 0.13038(9) 1.2523(2) 0.0229(5) Uani 1 1 d . . . H3 H 0.0156 0.1566 1.3105 0.027 Uiso 1 1 calc R . . C4 C 0.0798(2) 0.08886(9) 1.2981(2) 0.0232(5) Uani 1 1 d . . . H4 H 0.1027 0.0867 1.3876 0.028 Uiso 1 1 calc R . . C5 C 0.1561(2) 0.00476(9) 1.2569(3) 0.0271(5) Uani 1 1 d . . . H5 H 0.1803 0.0023 1.3459 0.033 Uiso 1 1 calc R . . C6 C 0.1743(2) -0.03355(10) 1.1732(3) 0.0310(6) Uani 1 1 d . . . H6 H 0.2107 -0.0620 1.2046 0.037 Uiso 1 1 calc R . . C7 C 0.1377(3) -0.02987(9) 1.0380(3) 0.0294(6) Uani 1 1 d . . . H7 H 0.1492 -0.0563 0.9808 0.035 Uiso 1 1 calc R . . C8 C 0.0858(2) 0.01171(9) 0.9899(3) 0.0224(5) Uani 1 1 d . . . H8 H 0.0640 0.0136 0.9000 0.027 Uiso 1 1 calc R . . C9 C 0.06441(19) 0.05242(8) 1.0760(2) 0.0160(4) Uani 1 1 d . . . C10 C 0.1006(2) 0.04861(9) 1.2116(2) 0.0200(5) Uani 1 1 d . . . C21 C -0.0702(2) 0.18232(8) 1.0753(2) 0.0201(5) Uani 1 1 d . . . O22 O -0.15138(16) 0.18191(6) 0.98720(18) 0.0246(4) Uani 1 1 d . . . O23 O -0.03158(18) 0.21986(6) 1.13421(18) 0.0276(4) Uani 1 1 d . . . C11 C -0.0270(2) 0.09934(8) 0.8841(2) 0.0170(4) Uani 1 1 d . . . C12 C 0.0440(2) 0.12556(8) 0.7965(2) 0.0182(4) Uani 1 1 d . . . C13 C 0.0149(2) 0.12776(10) 0.6581(3) 0.0258(5) Uani 1 1 d . . . H13 H 0.0639 0.1456 0.6001 0.031 Uiso 1 1 calc R . . C14 C -0.0834(2) 0.10414(10) 0.6100(2) 0.0260(5) Uani 1 1 d . . . H14 H -0.0998 0.1050 0.5186 0.031 Uiso 1 1 calc R . . C15 C -0.2702(2) 0.05619(9) 0.6505(3) 0.0262(5) Uani 1 1 d . . . H15 H -0.2892 0.0576 0.5599 0.031 Uiso 1 1 calc R . . C16 C -0.3470(2) 0.03314(10) 0.7368(3) 0.0290(6) Uani 1 1 d . . . H16 H -0.4178 0.0190 0.7046 0.035 Uiso 1 1 calc R . . C17 C -0.3197(2) 0.03074(9) 0.8742(3) 0.0266(5) Uani 1 1 d . . . H17 H -0.3727 0.0151 0.9324 0.032 Uiso 1 1 calc R . . C18 C -0.2157(2) 0.05126(9) 0.9233(2) 0.0210(5) Uani 1 1 d . . . H18 H -0.1987 0.0492 1.0144 0.025 Uiso 1 1 calc R . . C19 C -0.1331(2) 0.07572(8) 0.8359(2) 0.0168(4) Uani 1 1 d . . . C20 C -0.1620(2) 0.07803(9) 0.6967(2) 0.0211(5) Uani 1 1 d . . . O25 O 0.24448(16) 0.12945(6) 0.87793(19) 0.0273(4) Uani 1 1 d . . . O26 O 0.14149(17) 0.19886(6) 0.8571(2) 0.0289(4) Uani 1 1 d . . . C24 C 0.1526(2) 0.15329(8) 0.8477(2) 0.0198(5) Uani 1 1 d . . . C31 C 0.4997(3) 0.14714(12) 1.1531(3) 0.0382(7) Uani 1 1 d . . . C32 C 0.6056(3) 0.1515(2) 1.2230(4) 0.0632(12) Uani 1 1 d . . . H32 H 0.6394 0.1820 1.2396 0.076 Uiso 1 1 calc R . . C33 C 0.6639(4) 0.1072(2) 1.2707(4) 0.0754(16) Uani 1 1 d . . . H33 H 0.7374 0.1089 1.3160 0.090 Uiso 1 1 calc R . . C34 C 0.6096(5) 0.0632(2) 1.2483(5) 0.0766(16) Uani 1 1 d . . . H34 H 0.6459 0.0351 1.2819 0.092 Uiso 1 1 calc R . . C35 C 0.5062(5) 0.05891(15) 1.1800(4) 0.0646(13) Uani 1 1 d . . . H35 H 0.4718 0.0283 1.1660 0.078 Uiso 1 1 calc R . . C36 C 0.4506(4) 0.10061(12) 1.1301(3) 0.0488(9) Uani 1 1 d . . . H36 H 0.3796 0.0977 1.0805 0.059 Uiso 1 1 calc R . . C37 C 0.4362(2) 0.19207(9) 1.0982(2) 0.0236(5) Uani 1 1 d . . . H37 H 0.4835 0.2212 1.1214 0.028 Uiso 1 1 calc R . . N38 N 0.42848(17) 0.18806(7) 0.9494(2) 0.0194(4) Uani 1 1 d . . . H38A H 0.4953 0.1739 0.9181 0.029 Uiso 1 1 calc R . . H38B H 0.4212 0.2178 0.9140 0.029 Uiso 1 1 calc R . . H38C H 0.3643 0.1701 0.9272 0.029 Uiso 1 1 calc R . . C39 C 0.3169(3) 0.20949(10) 1.3081(3) 0.0297(6) Uani 1 1 d . . . C40 C 0.3366(5) 0.25711(13) 1.3492(4) 0.0687(14) Uani 1 1 d . . . H40 H 0.3436 0.2821 1.2866 0.082 Uiso 1 1 calc R . . C41 C 0.3457(7) 0.26718(15) 1.4858(4) 0.093(2) Uani 1 1 d . . . H41 H 0.3572 0.2993 1.5135 0.112 Uiso 1 1 calc R . . C42 C 0.3381(5) 0.23095(15) 1.5800(4) 0.0682(13) Uani 1 1 d . . . H42 H 0.3440 0.2382 1.6708 0.082 Uiso 1 1 calc R . . C43 C 0.3214(3) 0.18362(13) 1.5379(3) 0.0440(8) Uani 1 1 d . . . H43 H 0.3173 0.1586 1.6008 0.053 Uiso 1 1 calc R . . C44 C 0.3107(3) 0.17264(10) 1.4038(3) 0.0313(6) Uani 1 1 d . . . H44 H 0.2992 0.1404 1.3771 0.038 Uiso 1 1 calc R . . C45 C 0.3086(2) 0.19657(9) 1.1607(2) 0.0223(5) Uani 1 1 d . . . H45 H 0.2682 0.1648 1.1528 0.027 Uiso 1 1 calc R . . N46 N 0.23451(19) 0.23366(7) 1.0865(2) 0.0230(4) Uani 1 1 d . . . H46A H 0.1691 0.2411 1.1344 0.034 Uiso 1 1 calc R . . H46B H 0.2119 0.2214 1.0078 0.034 Uiso 1 1 calc R . . H46C H 0.2785 0.2605 1.0733 0.034 Uiso 1 1 calc R . . O51 O -0.35182(19) 0.15789(8) 0.8423(2) 0.0369(5) Uani 1 1 d . . . H51A H -0.279(4) 0.1560(13) 0.893(4) 0.050 Uiso 1 1 d . . . H51B H -0.351(4) 0.1403(15) 0.778(4) 0.050 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 0.0139(9) 0.0148(10) 0.0167(10) 0.0015(8) 0.0021(8) -0.0033(8) C2 0.0213(10) 0.0147(10) 0.0180(11) -0.0006(8) 0.0020(9) -0.0029(8) C3 0.0279(12) 0.0239(12) 0.0169(11) -0.0051(9) 0.0007(10) -0.0027(10) C4 0.0261(12) 0.0266(12) 0.0168(11) 0.0017(9) -0.0048(9) -0.0062(10) C5 0.0226(11) 0.0295(13) 0.0293(13) 0.0121(11) -0.0079(10) 0.0000(10) C6 0.0238(12) 0.0245(12) 0.0446(17) 0.0108(11) -0.0012(12) 0.0047(10) C7 0.0329(14) 0.0206(12) 0.0346(14) -0.0002(10) 0.0075(12) 0.0043(10) C8 0.0230(11) 0.0220(11) 0.0222(12) 0.0022(9) 0.0017(9) 0.0001(9) C9 0.0130(9) 0.0156(10) 0.0196(10) 0.0031(8) 0.0022(8) -0.0025(8) C10 0.0167(10) 0.0205(11) 0.0229(11) 0.0048(9) -0.0029(9) -0.0032(9) C21 0.0235(11) 0.0168(10) 0.0202(11) -0.0003(9) 0.0050(9) 0.0001(9) O22 0.0232(8) 0.0187(8) 0.0318(9) 0.0005(7) -0.0013(7) 0.0013(7) O23 0.0403(10) 0.0172(8) 0.0253(9) -0.0032(7) -0.0033(8) 0.0011(7) C11 0.0174(10) 0.0140(10) 0.0198(11) -0.0025(8) -0.0003(8) 0.0016(8) C12 0.0192(10) 0.0169(10) 0.0186(11) -0.0018(8) 0.0003(9) -0.0023(8) C13 0.0258(12) 0.0325(13) 0.0191(12) 0.0031(10) 0.0037(10) -0.0060(10) C14 0.0296(12) 0.0342(13) 0.0142(11) -0.0001(10) -0.0021(9) -0.0041(11) C15 0.0266(12) 0.0302(13) 0.0219(12) -0.0044(10) -0.0050(10) 0.0011(10) C16 0.0200(11) 0.0290(13) 0.0378(15) -0.0048(11) -0.0068(11) -0.0042(10) C17 0.0232(12) 0.0273(12) 0.0292(13) 0.0014(10) 0.0051(10) -0.0063(10) C18 0.0223(11) 0.0197(11) 0.0209(11) -0.0002(9) 0.0016(9) -0.0026(9) C19 0.0163(10) 0.0159(10) 0.0183(10) -0.0024(8) 0.0013(9) 0.0017(8) C20 0.0217(11) 0.0217(11) 0.0200(11) -0.0030(9) -0.0019(9) 0.0003(9) O25 0.0209(8) 0.0231(8) 0.0377(11) -0.0073(8) -0.0032(8) -0.0029(7) O26 0.0318(9) 0.0212(8) 0.0338(10) -0.0013(8) -0.0095(8) -0.0042(7) C24 0.0223(11) 0.0222(11) 0.0149(10) -0.0003(9) 0.0026(9) -0.0068(9) C31 0.0337(14) 0.0508(18) 0.0300(14) 0.0172(13) 0.0063(12) 0.0140(13) C32 0.0334(16) 0.114(4) 0.042(2) 0.034(2) -0.0030(15) 0.014(2) C33 0.0360(19) 0.144(5) 0.046(2) 0.037(3) 0.0047(16) 0.023(3) C34 0.076(3) 0.094(4) 0.060(3) 0.034(3) 0.028(2) 0.045(3) C35 0.096(3) 0.055(2) 0.042(2) 0.0218(17) 0.025(2) 0.039(2) C36 0.068(2) 0.0397(17) 0.0391(17) 0.0131(14) 0.0134(17) 0.0216(16) C37 0.0219(11) 0.0274(13) 0.0215(11) 0.0044(10) -0.0032(10) -0.0026(9) N38 0.0157(9) 0.0205(9) 0.0221(10) 0.0016(8) -0.0006(7) -0.0006(7) C39 0.0374(14) 0.0290(14) 0.0227(13) -0.0004(10) -0.0032(11) -0.0065(11) C40 0.144(4) 0.0355(17) 0.0268(16) 0.0035(14) -0.014(2) -0.022(2) C41 0.209(7) 0.040(2) 0.0306(19) -0.0062(16) -0.014(3) -0.021(3) C42 0.127(4) 0.055(2) 0.0226(16) -0.0005(15) -0.011(2) -0.016(3) C43 0.057(2) 0.0493(19) 0.0261(14) 0.0088(13) -0.0024(14) -0.0127(16) C44 0.0395(15) 0.0270(13) 0.0275(13) 0.0018(11) 0.0004(12) -0.0089(11) C45 0.0286(12) 0.0174(10) 0.0209(11) 0.0017(9) 0.0001(10) -0.0030(9) N46 0.0247(10) 0.0208(10) 0.0234(10) -0.0015(8) 0.0038(8) 0.0015(8) O51 0.0245(9) 0.0426(12) 0.0438(12) -0.0134(10) -0.0016(10) 0.0066(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.382(3) . ? C1 C9 1.436(3) . ? C1 C11 1.492(3) . ? C2 C3 1.424(3) . ? C2 C21 1.516(3) . ? C3 C4 1.356(4) . ? C4 C10 1.418(3) . ? C5 C6 1.355(4) . ? C5 C10 1.421(3) . ? C6 C7 1.413(4) . ? C7 C8 1.361(4) . ? C8 C9 1.425(3) . ? C9 C10 1.415(3) . ? C21 O22 1.256(3) . ? C21 O23 1.257(3) . ? C11 C12 1.376(3) . ? C11 C19 1.422(3) . ? C12 C13 1.419(3) . ? C12 C24 1.509(3) . ? C13 C14 1.352(4) . ? C14 C20 1.419(3) . ? C15 C16 1.364(4) . ? C15 C20 1.413(3) . ? C16 C17 1.406(4) . ? C17 C18 1.369(3) . ? C18 C19 1.429(3) . ? C19 C20 1.427(3) . ? O25 C24 1.243(3) . ? O26 C24 1.256(3) . ? C31 C32 1.367(5) . ? C31 C36 1.402(5) . ? C31 C37 1.517(4) . ? C32 C33 1.451(6) . ? C33 C34 1.364(8) . ? C34 C35 1.335(8) . ? C35 C36 1.388(5) . ? C37 N38 1.491(3) . ? C37 C45 1.546(4) . ? C39 C40 1.382(4) . ? C39 C44 1.390(4) . ? C39 C45 1.516(4) . ? C40 C41 1.394(5) . ? C41 C42 1.368(5) . ? C42 C43 1.373(5) . ? C43 C44 1.376(4) . ? C45 N46 1.499(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C9 119.2(2) . . ? C2 C1 C11 122.2(2) . . ? C9 C1 C11 118.44(19) . . ? C1 C2 C3 120.0(2) . . ? C1 C2 C21 122.9(2) . . ? C3 C2 C21 117.1(2) . . ? C4 C3 C2 121.1(2) . . ? C3 C4 C10 121.0(2) . . ? C6 C5 C10 121.4(2) . . ? C5 C6 C7 119.4(2) . . ? C8 C7 C6 121.1(3) . . ? C7 C8 C9 120.7(2) . . ? C10 C9 C8 118.2(2) . . ? C10 C9 C1 120.1(2) . . ? C8 C9 C1 121.8(2) . . ? C9 C10 C4 118.7(2) . . ? C9 C10 C5 119.3(2) . . ? C4 C10 C5 122.1(2) . . ? O22 C21 O23 125.2(2) . . ? O22 C21 C2 119.2(2) . . ? O23 C21 C2 115.6(2) . . ? C12 C11 C19 119.4(2) . . ? C12 C11 C1 120.3(2) . . ? C19 C11 C1 120.3(2) . . ? C11 C12 C13 120.8(2) . . ? C11 C12 C24 120.0(2) . . ? C13 C12 C24 119.2(2) . . ? C14 C13 C12 120.5(2) . . ? C13 C14 C20 121.0(2) . . ? C16 C15 C20 121.1(2) . . ? C15 C16 C17 120.2(2) . . ? C18 C17 C16 120.7(2) . . ? C17 C18 C19 120.6(2) . . ? C11 C19 C20 119.6(2) . . ? C11 C19 C18 122.1(2) . . ? C20 C19 C18 118.2(2) . . ? C15 C20 C14 122.1(2) . . ? C15 C20 C19 119.2(2) . . ? C14 C20 C19 118.6(2) . . ? O25 C24 O26 125.6(2) . . ? O25 C24 C12 117.9(2) . . ? O26 C24 C12 116.5(2) . . ? C32 C31 C36 119.6(3) . . ? C32 C31 C37 120.6(3) . . ? C36 C31 C37 119.8(3) . . ? C31 C32 C33 118.3(5) . . ? C34 C33 C32 119.1(4) . . ? C35 C34 C33 122.5(4) . . ? C34 C35 C36 119.3(5) . . ? C35 C36 C31 121.0(4) . . ? N38 C37 C31 109.1(2) . . ? N38 C37 C45 110.82(19) . . ? C31 C37 C45 109.9(2) . . ? C40 C39 C44 119.1(3) . . ? C40 C39 C45 121.2(3) . . ? C44 C39 C45 119.7(2) . . ? C39 C40 C41 119.2(3) . . ? C42 C41 C40 121.6(4) . . ? C41 C42 C43 118.7(3) . . ? C42 C43 C44 121.0(3) . . ? C43 C44 C39 120.4(3) . . ? N46 C45 C39 110.8(2) . . ? N46 C45 C37 110.63(19) . . ? C39 C45 C37 110.8(2) . . ? _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 27.90 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 0.542 _refine_diff_density_min -0.272 _refine_diff_density_rms 0.064 #===END data_imai5_2 _database_code_depnum_ccdc_archive 'CCDC 287389' #data_ima570a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C40 H42 N2 O6' _chemical_formula_weight 646.76 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 9.5831(6) _cell_length_b 18.4429(12) _cell_length_c 19.5963(12) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3463.5(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9999 _cell_measurement_theta_min 2.08 _cell_measurement_theta_max 27.88 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.65 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.240 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1376 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9479 _exptl_absorpt_correction_T_max 0.9917 _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 'Bruker APEX' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 21849 _diffrn_reflns_av_R_equivalents 0.0451 _diffrn_reflns_av_sigmaI/netI 0.0627 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.08 _diffrn_reflns_theta_max 27.88 _reflns_number_total 8076 _reflns_number_gt 6540 _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 ; Two 2-butanols of different chirality (from C61 to O65 and from C71 to O75) share the same site. Their occupancies were refined. The positions of the hydrogens attached to O65 and O75 were not assigned. 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^)+(0.0569P)^2^+1.1800P] 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 0.1(11) _refine_ls_number_reflns 8076 _refine_ls_number_parameters 437 _refine_ls_number_restraints 8 _refine_ls_R_factor_all 0.0740 _refine_ls_R_factor_gt 0.0561 _refine_ls_wR_factor_ref 0.1294 _refine_ls_wR_factor_gt 0.1208 _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_restrained_S_all 1.037 _refine_ls_shift/su_max 0.008 _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 0.9903(2) 0.09622(12) 0.14398(11) 0.0167(5) Uani 1 1 d . . . C2 C 1.1301(2) 0.11113(13) 0.15668(12) 0.0176(5) Uani 1 1 d . . . C3 C 1.1692(3) 0.14557(13) 0.21827(12) 0.0214(5) Uani 1 1 d . . . H3 H 1.2633 0.1540 0.2267 0.026 Uiso 1 1 calc R . . C4 C 1.0734(3) 0.16668(13) 0.26549(12) 0.0229(5) Uani 1 1 d . . . H4 H 1.1025 0.1871 0.3065 0.027 Uiso 1 1 calc R . . C5 C 0.8254(3) 0.18364(14) 0.29839(13) 0.0273(6) Uani 1 1 d . . . H5 H 0.8527 0.2049 0.3393 0.033 Uiso 1 1 calc R . . C6 C 0.6870(3) 0.17780(14) 0.28311(14) 0.0282(6) Uani 1 1 d . . . H6 H 0.6205 0.1960 0.3131 0.034 Uiso 1 1 calc R . . C7 C 0.6446(3) 0.14438(14) 0.22230(13) 0.0258(6) Uani 1 1 d . . . H7 H 0.5501 0.1416 0.2118 0.031 Uiso 1 1 calc R . . C8 C 0.7408(3) 0.11580(13) 0.17811(12) 0.0205(5) Uani 1 1 d . . . H8 H 0.7105 0.0921 0.1389 0.025 Uiso 1 1 calc R . . C9 C 0.8868(2) 0.12183(12) 0.19118(12) 0.0167(5) Uani 1 1 d . . . C10 C 0.9288(3) 0.15745(13) 0.25206(12) 0.0212(5) Uani 1 1 d . . . C11 C 0.9419(2) 0.05469(12) 0.08234(11) 0.0161(5) Uani 1 1 d . . . C12 C 0.8814(2) 0.08904(12) 0.02733(11) 0.0152(4) Uani 1 1 d . . . C13 C 0.8317(2) 0.04909(13) -0.02945(12) 0.0207(5) Uani 1 1 d . . . H13 H 0.7905 0.0733 -0.0659 0.025 Uiso 1 1 calc R . . C14 C 0.8438(3) -0.02399(14) -0.03113(13) 0.0252(5) Uani 1 1 d . . . H14 H 0.8138 -0.0495 -0.0694 0.030 Uiso 1 1 calc R . . C15 C 0.9144(3) -0.13860(14) 0.02473(15) 0.0343(7) Uani 1 1 d . . . H15 H 0.8859 -0.1646 -0.0135 0.041 Uiso 1 1 calc R . . C16 C 0.9672(3) -0.17476(15) 0.07935(15) 0.0366(7) Uani 1 1 d . . . H16 H 0.9744 -0.2250 0.0783 0.044 Uiso 1 1 calc R . . C17 C 1.0106(3) -0.13647(14) 0.13727(14) 0.0294(6) Uani 1 1 d . . . H17 H 1.0448 -0.1616 0.1749 0.035 Uiso 1 1 calc R . . C18 C 1.0032(3) -0.06257(13) 0.13894(12) 0.0226(5) Uani 1 1 d . . . H18 H 1.0338 -0.0379 0.1775 0.027 Uiso 1 1 calc R . . C19 C 0.9496(2) -0.02289(13) 0.08278(12) 0.0192(5) Uani 1 1 d . . . C20 C 0.9019(3) -0.06204(14) 0.02491(13) 0.0239(5) Uani 1 1 d . . . C21 C 1.2423(2) 0.09914(13) 0.10367(12) 0.0197(5) Uani 1 1 d . . . O22 O 1.21522(17) 0.06152(9) 0.05170(8) 0.0225(4) Uani 1 1 d . . . O23 O 1.35706(18) 0.13141(10) 0.11268(9) 0.0284(4) Uani 1 1 d . . . C24 C 0.8658(2) 0.17029(12) 0.02558(11) 0.0165(5) Uani 1 1 d . . . O25 O 0.96546(17) 0.20807(8) 0.04729(8) 0.0194(4) Uani 1 1 d . . . O26 O 0.75380(17) 0.19547(8) 0.00083(8) 0.0205(4) Uani 1 1 d . . . C31 C 1.2168(2) 0.09973(13) -0.15605(12) 0.0194(5) Uani 1 1 d . . . C32 C 1.1477(3) 0.03717(14) -0.13525(14) 0.0282(6) Uani 1 1 d . . . H32 H 1.1413 0.0259 -0.0891 0.034 Uiso 1 1 calc R . . C33 C 1.0880(3) -0.00860(16) -0.18368(15) 0.0366(7) Uani 1 1 d . . . H33 H 1.0402 -0.0499 -0.1696 0.044 Uiso 1 1 calc R . . C34 C 1.0992(3) 0.00685(16) -0.25222(14) 0.0327(7) Uani 1 1 d . . . H34 H 1.0600 -0.0242 -0.2843 0.039 Uiso 1 1 calc R . . C35 C 1.1684(3) 0.06813(17) -0.27311(14) 0.0348(7) Uani 1 1 d . . . H35 H 1.1767 0.0784 -0.3194 0.042 Uiso 1 1 calc R . . C36 C 1.2259(3) 0.11470(15) -0.22516(13) 0.0276(6) Uani 1 1 d . . . H36 H 1.2712 0.1566 -0.2396 0.033 Uiso 1 1 calc R . . C37 C 1.2876(2) 0.14861(13) -0.10498(11) 0.0169(5) Uani 1 1 d . . . H37 H 1.3180 0.1926 -0.1287 0.020 Uiso 1 1 calc R . . N38 N 1.18764(19) 0.17015(11) -0.04971(10) 0.0177(4) Uani 1 1 d . . . H38A H 1.1790 0.1339 -0.0200 0.027 Uiso 1 1 calc R . . H38B H 1.1048 0.1800 -0.0680 0.027 Uiso 1 1 calc R . . H38C H 1.2198 0.2093 -0.0283 0.027 Uiso 1 1 calc R . . C39 C 1.5281(2) 0.10137(12) -0.13001(11) 0.0171(5) Uani 1 1 d . . . C40 C 1.5707(2) 0.03208(13) -0.14898(12) 0.0204(5) Uani 1 1 d . . . H40 H 1.5280 -0.0083 -0.1297 0.024 Uiso 1 1 calc R . . C41 C 1.6773(3) 0.02295(14) -0.19670(13) 0.0243(5) Uani 1 1 d . . . H41 H 1.7063 -0.0234 -0.2088 0.029 Uiso 1 1 calc R . . C42 C 1.7396(3) 0.08279(14) -0.22594(12) 0.0251(5) Uani 1 1 d . . . H42 H 1.8111 0.0767 -0.2575 0.030 Uiso 1 1 calc R . . C43 C 1.6961(3) 0.15179(14) -0.20842(12) 0.0232(5) Uani 1 1 d . . . H43 H 1.7370 0.1919 -0.2290 0.028 Uiso 1 1 calc R . . C44 C 1.5913(2) 0.16148(13) -0.16008(12) 0.0209(5) Uani 1 1 d . . . H44 H 1.5634 0.2080 -0.1479 0.025 Uiso 1 1 calc R . . C45 C 1.4181(2) 0.11035(12) -0.07562(11) 0.0158(4) Uani 1 1 d . . . H45 H 1.3905 0.0621 -0.0596 0.019 Uiso 1 1 calc R . . N46 N 1.47670(19) 0.15182(10) -0.01631(9) 0.0169(4) Uani 1 1 d . . . H46A H 1.4616 0.1990 -0.0224 0.025 Uiso 1 1 calc R . . H46B H 1.5680 0.1437 -0.0133 0.025 Uiso 1 1 calc R . . H46C H 1.4352 0.1374 0.0220 0.025 Uiso 1 1 calc R . . O51 O 1.9576(2) 0.22610(12) -0.12371(10) 0.0309(5) Uani 1 1 d . . . C61 C 1.3042(7) -0.1308(4) -0.0358(4) 0.0466(18) Uiso 0.601(8) 1 d PD A 1 H61A H 1.2204 -0.1024 -0.0385 0.070 Uiso 0.601(8) 1 calc PR A 1 H61B H 1.2809 -0.1813 -0.0375 0.070 Uiso 0.601(8) 1 calc PR A 1 H61C H 1.3639 -0.1189 -0.0736 0.070 Uiso 0.601(8) 1 calc PR A 1 C62 C 1.3801(6) -0.1141(3) 0.0315(3) 0.0412(15) Uiso 0.601(8) 1 d PD A 1 H62 H 1.3196 -0.1167 0.0718 0.049 Uiso 0.601(8) 1 calc PR A 1 C63 C 1.5138(6) -0.1588(3) 0.0382(3) 0.0423(16) Uiso 0.601(8) 1 d PD A 1 H63A H 1.5790 -0.1448 0.0027 0.051 Uiso 0.601(8) 1 calc PR A 1 H63B H 1.4923 -0.2098 0.0324 0.051 Uiso 0.601(8) 1 calc PR A 1 C64 C 1.5807(8) -0.1467(4) 0.1084(4) 0.0572(19) Uiso 0.601(8) 1 d PD A 1 H64A H 1.6649 -0.1747 0.1116 0.086 Uiso 0.601(8) 1 calc PR A 1 H64B H 1.5168 -0.1616 0.1434 0.086 Uiso 0.601(8) 1 calc PR A 1 H64C H 1.6022 -0.0962 0.1140 0.086 Uiso 0.601(8) 1 calc PR A 1 O65 O 1.4229(6) -0.0395(3) 0.0135(3) 0.0707(17) Uiso 0.601(8) 1 d PD A 1 C71 C 1.2806(19) -0.1201(11) -0.0512(9) 0.123(8) Uiso 0.399(8) 1 d PD A 2 H71A H 1.2911 -0.0873 -0.0889 0.185 Uiso 0.399(8) 1 calc PR A 2 H71B H 1.1971 -0.1083 -0.0264 0.185 Uiso 0.399(8) 1 calc PR A 2 H71C H 1.2744 -0.1689 -0.0680 0.185 Uiso 0.399(8) 1 calc PR A 2 C72 C 1.4056(13) -0.1134(6) -0.0042(6) 0.075(4) Uiso 0.399(8) 1 d PD A 2 H72 H 1.4918 -0.1226 -0.0297 0.089 Uiso 0.399(8) 1 calc PR A 2 C73 C 1.3993(12) -0.1622(6) 0.0587(5) 0.074(4) Uiso 0.399(8) 1 d PD A 2 H73A H 1.3312 -0.1429 0.0905 0.089 Uiso 0.399(8) 1 calc PR A 2 H73B H 1.3685 -0.2102 0.0451 0.089 Uiso 0.399(8) 1 calc PR A 2 C74 C 1.5404(18) -0.1682(10) 0.0943(9) 0.119(7) Uiso 0.399(8) 1 d PD A 2 H74A H 1.5324 -0.2000 0.1329 0.179 Uiso 0.399(8) 1 calc PR A 2 H74B H 1.5696 -0.1211 0.1094 0.179 Uiso 0.399(8) 1 calc PR A 2 H74C H 1.6082 -0.1874 0.0630 0.179 Uiso 0.399(8) 1 calc PR A 2 O75 O 1.4225(6) -0.0422(3) 0.0419(4) 0.0367(16) Uiso 0.399(8) 1 d PD A 2 H51A H 1.933(4) 0.273(2) -0.1265(17) 0.050 Uiso 1 1 d . . . H51B H 1.893(4) 0.202(2) -0.1163(18) 0.050 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 0.0184(11) 0.0154(11) 0.0164(11) 0.0028(9) -0.0034(9) -0.0010(9) C2 0.0162(11) 0.0173(12) 0.0194(11) 0.0028(9) 0.0002(9) -0.0016(9) C3 0.0177(12) 0.0240(13) 0.0226(12) 0.0035(10) -0.0048(10) -0.0027(10) C4 0.0251(13) 0.0240(13) 0.0196(12) -0.0019(10) -0.0034(10) -0.0060(11) C5 0.0324(15) 0.0254(14) 0.0241(13) -0.0051(10) 0.0050(11) -0.0021(12) C6 0.0270(14) 0.0236(14) 0.0340(15) -0.0014(11) 0.0107(12) 0.0023(11) C7 0.0201(12) 0.0255(13) 0.0318(14) 0.0061(11) 0.0040(11) 0.0031(10) C8 0.0198(12) 0.0189(12) 0.0228(12) 0.0040(9) -0.0012(10) -0.0009(10) C9 0.0168(11) 0.0144(11) 0.0189(11) 0.0058(9) 0.0008(9) -0.0004(9) C10 0.0224(12) 0.0182(12) 0.0231(12) 0.0002(9) 0.0014(10) -0.0021(10) C11 0.0102(11) 0.0172(12) 0.0210(12) -0.0013(9) 0.0028(9) -0.0009(9) C12 0.0092(10) 0.0174(11) 0.0189(11) -0.0003(9) 0.0016(8) -0.0005(9) C13 0.0171(12) 0.0224(13) 0.0228(12) 0.0015(10) -0.0042(10) 0.0013(10) C14 0.0270(14) 0.0234(13) 0.0251(13) -0.0053(10) -0.0092(10) -0.0015(11) C15 0.0464(18) 0.0215(14) 0.0349(15) -0.0050(11) -0.0131(14) 0.0021(13) C16 0.0465(18) 0.0166(13) 0.0469(18) 0.0019(12) -0.0115(15) 0.0027(12) C17 0.0337(15) 0.0226(14) 0.0320(14) 0.0054(11) -0.0048(12) 0.0014(11) C18 0.0232(13) 0.0230(13) 0.0215(12) 0.0000(10) -0.0013(10) -0.0002(10) C19 0.0148(11) 0.0195(12) 0.0234(12) 0.0008(9) 0.0007(9) -0.0018(9) C20 0.0222(13) 0.0208(12) 0.0288(13) -0.0012(10) -0.0043(11) 0.0027(10) C21 0.0167(11) 0.0219(12) 0.0205(11) 0.0071(9) -0.0026(9) -0.0004(10) O22 0.0176(9) 0.0275(9) 0.0225(9) -0.0014(7) 0.0016(7) 0.0002(7) O23 0.0184(9) 0.0398(11) 0.0269(10) 0.0011(8) 0.0010(7) -0.0103(8) C24 0.0145(11) 0.0200(12) 0.0150(11) 0.0003(9) 0.0028(9) -0.0005(9) O25 0.0160(8) 0.0176(9) 0.0246(9) 0.0010(7) -0.0036(7) -0.0019(6) O26 0.0122(8) 0.0196(8) 0.0296(9) 0.0004(7) -0.0041(7) 0.0027(7) C31 0.0114(11) 0.0228(13) 0.0240(12) -0.0038(9) -0.0006(9) 0.0034(9) C32 0.0281(14) 0.0296(15) 0.0269(13) -0.0041(11) -0.0002(11) -0.0047(11) C33 0.0311(15) 0.0310(16) 0.0477(18) -0.0120(13) 0.0012(13) -0.0098(13) C34 0.0214(13) 0.0397(17) 0.0372(15) -0.0189(13) -0.0039(11) 0.0013(12) C35 0.0284(15) 0.0505(18) 0.0254(14) -0.0076(12) -0.0010(11) 0.0041(13) C36 0.0242(13) 0.0302(14) 0.0285(13) 0.0005(11) -0.0001(11) -0.0032(11) C37 0.0118(11) 0.0195(12) 0.0195(11) 0.0001(9) 0.0013(9) 0.0008(9) N38 0.0115(9) 0.0195(10) 0.0220(10) -0.0022(8) -0.0001(8) 0.0009(8) C39 0.0105(10) 0.0211(12) 0.0197(11) -0.0016(9) -0.0035(9) 0.0004(9) C40 0.0172(12) 0.0193(12) 0.0246(12) -0.0032(9) -0.0019(10) -0.0009(10) C41 0.0218(13) 0.0248(13) 0.0262(13) -0.0111(10) -0.0047(10) 0.0050(11) C42 0.0178(12) 0.0367(15) 0.0207(12) -0.0066(11) 0.0014(10) 0.0045(11) C43 0.0176(12) 0.0295(14) 0.0224(12) 0.0005(10) 0.0022(10) -0.0025(10) C44 0.0170(12) 0.0198(12) 0.0260(12) -0.0020(10) 0.0006(10) 0.0018(10) C45 0.0114(10) 0.0150(11) 0.0210(11) -0.0010(9) -0.0018(9) -0.0003(9) N46 0.0103(9) 0.0175(10) 0.0228(10) 0.0012(8) 0.0008(8) 0.0002(8) O51 0.0234(10) 0.0296(11) 0.0398(11) 0.0046(9) -0.0053(9) -0.0034(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.390(3) . ? C1 C9 1.436(3) . ? C1 C11 1.503(3) . ? C2 C3 1.414(3) . ? C2 C21 1.511(3) . ? C3 C4 1.361(3) . ? C4 C10 1.421(3) . ? C5 C6 1.365(4) . ? C5 C10 1.428(3) . ? C6 C7 1.402(4) . ? C7 C8 1.370(3) . ? C8 C9 1.427(3) . ? C9 C10 1.420(3) . ? C11 C12 1.378(3) . ? C11 C19 1.433(3) . ? C12 C13 1.417(3) . ? C12 C24 1.506(3) . ? C13 C14 1.353(3) . ? C14 C20 1.417(3) . ? C15 C16 1.359(4) . ? C15 C20 1.417(4) . ? C16 C17 1.400(4) . ? C17 C18 1.365(4) . ? C18 C19 1.418(3) . ? C19 C20 1.420(3) . ? C21 O22 1.259(3) . ? C21 O23 1.263(3) . ? C24 O25 1.257(3) . ? C24 O26 1.266(3) . ? C31 C36 1.385(3) . ? C31 C32 1.391(4) . ? C31 C37 1.508(3) . ? C32 C33 1.393(4) . ? C33 C34 1.377(4) . ? C34 C35 1.373(4) . ? C35 C36 1.387(4) . ? C37 N38 1.500(3) . ? C37 C45 1.547(3) . ? C39 C40 1.392(3) . ? C39 C44 1.394(3) . ? C39 C45 1.508(3) . ? C40 C41 1.395(3) . ? C41 C42 1.379(4) . ? C42 C43 1.382(4) . ? C43 C44 1.392(3) . ? C45 N46 1.500(3) . ? C61 C62 1.538(8) . ? C62 O65 1.478(7) . ? C62 C63 1.528(7) . ? C63 C64 1.533(9) . ? C71 C72 1.516(14) . ? C72 C73 1.527(13) . ? C72 O75 1.602(11) . ? C73 C74 1.527(15) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C9 119.0(2) . . ? C2 C1 C11 122.8(2) . . ? C9 C1 C11 118.2(2) . . ? C1 C2 C3 119.8(2) . . ? C1 C2 C21 122.2(2) . . ? C3 C2 C21 117.6(2) . . ? C4 C3 C2 122.0(2) . . ? C3 C4 C10 119.9(2) . . ? C6 C5 C10 120.6(2) . . ? C5 C6 C7 120.2(2) . . ? C8 C7 C6 120.7(2) . . ? C7 C8 C9 121.1(2) . . ? C10 C9 C8 117.7(2) . . ? C10 C9 C1 119.9(2) . . ? C8 C9 C1 122.4(2) . . ? C9 C10 C4 119.2(2) . . ? C9 C10 C5 119.6(2) . . ? C4 C10 C5 121.2(2) . . ? C12 C11 C19 119.0(2) . . ? C12 C11 C1 121.6(2) . . ? C19 C11 C1 119.2(2) . . ? C11 C12 C13 121.1(2) . . ? C11 C12 C24 121.1(2) . . ? C13 C12 C24 117.8(2) . . ? C14 C13 C12 120.5(2) . . ? C13 C14 C20 120.5(2) . . ? C16 C15 C20 121.2(3) . . ? C15 C16 C17 120.1(2) . . ? C18 C17 C16 120.5(2) . . ? C17 C18 C19 121.0(2) . . ? C18 C19 C20 118.3(2) . . ? C18 C19 C11 122.6(2) . . ? C20 C19 C11 119.1(2) . . ? C15 C20 C14 121.6(2) . . ? C15 C20 C19 118.8(2) . . ? C14 C20 C19 119.6(2) . . ? O22 C21 O23 123.5(2) . . ? O22 C21 C2 119.4(2) . . ? O23 C21 C2 117.0(2) . . ? O25 C24 O26 124.8(2) . . ? O25 C24 C12 117.9(2) . . ? O26 C24 C12 117.2(2) . . ? C36 C31 C32 118.8(2) . . ? C36 C31 C37 120.1(2) . . ? C32 C31 C37 121.0(2) . . ? C31 C32 C33 119.9(3) . . ? C34 C33 C32 120.5(3) . . ? C35 C34 C33 119.9(2) . . ? C34 C35 C36 120.0(3) . . ? C31 C36 C35 120.9(3) . . ? N38 C37 C31 110.50(18) . . ? N38 C37 C45 111.62(18) . . ? C31 C37 C45 109.76(18) . . ? C40 C39 C44 119.3(2) . . ? C40 C39 C45 119.6(2) . . ? C44 C39 C45 121.0(2) . . ? C39 C40 C41 120.3(2) . . ? C42 C41 C40 119.9(2) . . ? C41 C42 C43 120.2(2) . . ? C42 C43 C44 120.3(2) . . ? C43 C44 C39 119.9(2) . . ? N46 C45 C39 109.97(17) . . ? N46 C45 C37 111.00(18) . . ? C39 C45 C37 110.62(18) . . ? O65 C62 C63 106.9(4) . . ? O65 C62 C61 96.4(5) . . ? C63 C62 C61 111.3(5) . . ? C62 C63 C64 110.4(5) . . ? C71 C72 C73 114.2(11) . . ? C71 C72 O75 119.2(11) . . ? C73 C72 O75 91.9(8) . . ? C74 C73 C72 112.1(11) . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 27.88 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.374 _refine_diff_density_min -0.334 _refine_diff_density_rms 0.053 #===END data_imai5_3 _database_code_depnum_ccdc_archive 'CCDC 287390' #data_4689a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C41 H44 N2 O6' _chemical_formula_weight 660.78 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 9.5068(6) _cell_length_b 18.9504(11) _cell_length_c 19.9816(12) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3599.8(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9999 _cell_measurement_theta_min 1.48 _cell_measurement_theta_max 27.87 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.219 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1408 _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9839 _exptl_absorpt_correction_T_max 0.9919 _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 'Bruker APEX' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 22810 _diffrn_reflns_av_R_equivalents 0.0486 _diffrn_reflns_av_sigmaI/netI 0.0716 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.48 _diffrn_reflns_theta_max 27.87 _reflns_number_total 8093 _reflns_number_gt 5760 _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^)+(0.0907P)^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 0.1(13) _refine_ls_number_reflns 8093 _refine_ls_number_parameters 451 _refine_ls_number_restraints 5 _refine_ls_R_factor_all 0.0885 _refine_ls_R_factor_gt 0.0605 _refine_ls_wR_factor_ref 0.1588 _refine_ls_wR_factor_gt 0.1484 _refine_ls_goodness_of_fit_ref 1.015 _refine_ls_restrained_S_all 1.024 _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 0.9557(3) 0.43919(14) 0.91538(13) 0.0234(6) Uani 1 1 d . . . C2 C 0.8975(3) 0.40707(13) 0.97060(13) 0.0212(6) Uani 1 1 d . . . C3 C 0.8549(3) 0.44632(15) 1.02704(14) 0.0264(6) Uani 1 1 d . . . H3 H 0.8159 0.4233 1.0637 0.032 Uiso 1 1 calc R . . C4 C 0.8706(3) 0.51786(15) 1.02815(15) 0.0327(7) Uani 1 1 d . . . H4 H 0.8472 0.5432 1.0664 0.039 Uiso 1 1 calc R . . C5 C 0.9344(4) 0.62845(16) 0.96938(18) 0.0448(9) Uani 1 1 d . . . H5 H 0.9124 0.6544 1.0075 0.054 Uiso 1 1 calc R . . C6 C 0.9770(4) 0.66243(18) 0.91334(18) 0.0526(10) Uani 1 1 d . . . H6 H 0.9810 0.7115 0.9127 0.063 Uiso 1 1 calc R . . C7 C 1.0153(4) 0.62397(17) 0.85626(17) 0.0443(8) Uani 1 1 d . . . H7 H 1.0447 0.6477 0.8180 0.053 Uiso 1 1 calc R . . C8 C 1.0099(3) 0.55202(15) 0.85645(15) 0.0330(7) Uani 1 1 d . . . H8 H 1.0369 0.5272 0.8184 0.040 Uiso 1 1 calc R . . C9 C 0.9637(3) 0.51471(15) 0.91372(14) 0.0258(6) Uani 1 1 d . . . C10 C 0.9228(3) 0.55376(15) 0.97072(15) 0.0303(7) Uani 1 1 d . . . C21 C 0.8802(3) 0.32788(13) 0.97325(13) 0.0199(6) Uani 1 1 d . . . O22 O 0.76870(19) 0.30432(9) 0.99946(10) 0.0257(4) Uani 1 1 d . . . O23 O 0.9783(2) 0.29041(9) 0.95116(9) 0.0240(4) Uani 1 1 d . . . C11 C 1.0022(3) 0.39760(14) 0.85490(13) 0.0233(6) Uani 1 1 d . . . C12 C 1.1412(3) 0.38110(14) 0.84302(13) 0.0234(6) Uani 1 1 d . . . C13 C 1.1789(3) 0.34503(15) 0.78343(14) 0.0287(7) Uani 1 1 d . . . H13 H 1.2731 0.3347 0.7754 0.034 Uiso 1 1 calc R . . C14 C 1.0813(3) 0.32543(15) 0.73828(14) 0.0310(7) Uani 1 1 d . . . H14 H 1.1095 0.3035 0.6989 0.037 Uiso 1 1 calc R . . C15 C 0.8315(3) 0.31338(16) 0.70529(16) 0.0337(7) Uani 1 1 d . . . H15 H 0.8576 0.2899 0.6663 0.040 Uiso 1 1 calc R . . C16 C 0.6926(3) 0.32384(16) 0.71871(16) 0.0353(7) Uani 1 1 d . . . H16 H 0.6245 0.3076 0.6890 0.042 Uiso 1 1 calc R . . C17 C 0.6525(3) 0.35905(16) 0.77728(15) 0.0315(7) Uani 1 1 d . . . H17 H 0.5574 0.3649 0.7868 0.038 Uiso 1 1 calc R . . C18 C 0.7501(3) 0.38476(14) 0.82037(15) 0.0267(6) Uani 1 1 d . . . H18 H 0.7210 0.4096 0.8580 0.032 Uiso 1 1 calc R . . C19 C 0.8968(3) 0.37422(14) 0.80882(14) 0.0230(6) Uani 1 1 d . . . C20 C 0.9368(3) 0.33773(14) 0.74987(14) 0.0268(6) Uani 1 1 d . . . C24 C 1.2566(3) 0.39352(15) 0.89475(14) 0.0263(6) Uani 1 1 d . . . O25 O 1.2278(2) 0.42874(11) 0.94661(9) 0.0298(5) Uani 1 1 d . . . O26 O 1.3738(2) 0.36471(11) 0.88503(10) 0.0352(5) Uani 1 1 d . . . C31 C 1.5416(3) 0.39943(15) 1.12439(13) 0.0240(6) Uani 1 1 d . . . C32 C 1.5745(3) 0.46890(15) 1.14267(14) 0.0275(6) Uani 1 1 d . . . H32 H 1.5281 0.5065 1.1225 0.033 Uiso 1 1 calc R . . C33 C 1.6760(3) 0.48138(17) 1.19077(15) 0.0344(7) Uani 1 1 d . . . H33 H 1.6988 0.5274 1.2027 0.041 Uiso 1 1 calc R . . C34 C 1.7442(4) 0.42491(18) 1.22132(15) 0.0387(8) Uani 1 1 d . . . H34 H 1.8130 0.4334 1.2534 0.046 Uiso 1 1 calc R . . C35 C 1.7104(3) 0.35670(18) 1.20436(15) 0.0361(7) Uani 1 1 d . . . H35 H 1.7554 0.3192 1.2255 0.043 Uiso 1 1 calc R . . C36 C 1.6089(3) 0.34353(15) 1.15564(14) 0.0271(6) Uani 1 1 d . . . H36 H 1.5864 0.2973 1.1441 0.032 Uiso 1 1 calc R . . C37 C 1.4316(3) 0.38737(14) 1.07098(13) 0.0219(6) Uani 1 1 d . . . H37 H 1.4022 0.4333 1.0534 0.026 Uiso 1 1 calc R . . N38 N 1.4916(2) 0.34469(12) 1.01443(11) 0.0215(5) Uani 1 1 d . . . H38A H 1.4758 0.2991 1.0219 0.032 Uiso 1 1 calc R . . H38B H 1.5838 0.3523 1.0117 0.032 Uiso 1 1 calc R . . H38C H 1.4508 0.3575 0.9762 0.032 Uiso 1 1 calc R . . C39 C 1.2312(3) 0.39900(14) 1.15123(14) 0.0238(6) Uani 1 1 d . . . C40 C 1.1748(3) 0.46339(16) 1.13158(16) 0.0362(7) Uani 1 1 d . . . H40 H 1.1757 0.4765 1.0867 0.043 Uiso 1 1 calc R . . C41 C 1.1174(4) 0.50763(17) 1.17905(18) 0.0435(8) Uani 1 1 d . . . H41 H 1.0782 0.5504 1.1658 0.052 Uiso 1 1 calc R . . C42 C 1.1172(4) 0.48953(19) 1.24599(18) 0.0449(9) Uani 1 1 d . . . H42 H 1.0809 0.5204 1.2778 0.054 Uiso 1 1 calc R . . C43 C 1.1706(4) 0.4260(2) 1.26490(17) 0.0547(10) Uani 1 1 d . . . H43 H 1.1696 0.4130 1.3098 0.066 Uiso 1 1 calc R . . C44 C 1.2265(4) 0.38064(18) 1.21760(15) 0.0396(8) Uani 1 1 d . . . H44 H 1.2614 0.3370 1.2310 0.048 Uiso 1 1 calc R . . C45 C 1.3015(3) 0.35043(14) 1.10164(13) 0.0213(6) Uani 1 1 d . . . H45 H 1.3336 0.3083 1.1257 0.026 Uiso 1 1 calc R . . N46 N 1.1991(2) 0.32770(12) 1.04875(11) 0.0230(5) Uani 1 1 d . . . H46A H 1.1858 0.3628 1.0199 0.035 Uiso 1 1 calc R . . H46B H 1.1175 0.3164 1.0678 0.035 Uiso 1 1 calc R . . H46C H 1.2331 0.2903 1.0272 0.035 Uiso 1 1 calc R . . O51 O 1.3405(4) 0.54445(14) 1.00594(14) 0.0740(9) Uani 1 1 d D . . H51 H 1.3002 0.5170 0.9807 0.111 Uiso 1 1 calc R . . C52 C 1.3718(5) 0.6069(2) 0.9715(3) 0.104(2) Uani 1 1 d D . . H52 H 1.3139 0.6100 0.9310 0.124 Uiso 1 1 calc R . . C53 C 1.3286(7) 0.6667(3) 1.0216(3) 0.117(2) Uani 1 1 d D . . H53A H 1.2306 0.6621 1.0324 0.175 Uiso 1 1 calc R . . H53B H 1.3449 0.7119 1.0013 0.175 Uiso 1 1 calc R . . H53C H 1.3837 0.6627 1.0617 0.175 Uiso 1 1 calc R . . C54 C 1.5255(6) 0.6133(3) 0.9530(3) 0.117(2) Uani 1 1 d D . . H54 H 1.5814 0.6163 0.9941 0.140 Uiso 1 1 calc R . . C55 C 1.5552(6) 0.5418(3) 0.9188(2) 0.0835(16) Uani 1 1 d D . . H55A H 1.6518 0.5400 0.9048 0.125 Uiso 1 1 calc R . . H55B H 1.4952 0.5366 0.8804 0.125 Uiso 1 1 calc R . . H55C H 1.5371 0.5041 0.9498 0.125 Uiso 1 1 calc R . . C56 C 1.5454(7) 0.6816(3) 0.9128(3) 0.125(3) Uani 1 1 d D . . H56A H 1.6417 0.6853 0.8987 0.188 Uiso 1 1 calc R . . H56B H 1.5217 0.7213 0.9403 0.188 Uiso 1 1 calc R . . H56C H 1.4853 0.6807 0.8742 0.188 Uiso 1 1 calc R . . O61 O 1.9674(2) 0.27468(13) 1.12061(11) 0.0374(5) Uani 1 1 d . . . H61B H 1.942(4) 0.235(2) 1.1248(18) 0.050 Uiso 1 1 d . . . H61A H 1.899(4) 0.301(2) 1.1096(19) 0.050 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 0.0200(14) 0.0257(15) 0.0244(14) 0.0011(11) -0.0039(11) -0.0007(11) C2 0.0198(14) 0.0208(13) 0.0230(14) 0.0002(11) 0.0000(11) 0.0012(11) C3 0.0245(15) 0.0284(15) 0.0262(14) 0.0028(12) 0.0019(12) -0.0018(12) C4 0.0391(17) 0.0251(15) 0.0339(16) -0.0080(13) 0.0109(14) 0.0010(13) C5 0.062(2) 0.0277(17) 0.045(2) -0.0023(15) 0.0105(18) -0.0048(16) C6 0.078(3) 0.0215(16) 0.058(2) 0.0006(16) 0.013(2) -0.0029(17) C7 0.059(2) 0.0350(18) 0.0391(18) 0.0095(15) 0.0062(17) -0.0077(16) C8 0.0410(19) 0.0270(15) 0.0310(16) 0.0026(13) -0.0007(14) 0.0005(13) C9 0.0259(15) 0.0233(14) 0.0284(15) 0.0025(12) 0.0003(12) -0.0005(12) C10 0.0323(17) 0.0226(14) 0.0360(16) -0.0027(13) 0.0005(13) 0.0023(12) C21 0.0193(13) 0.0227(13) 0.0176(13) -0.0014(11) -0.0034(11) 0.0004(11) O22 0.0193(10) 0.0233(10) 0.0346(11) -0.0029(8) 0.0041(9) -0.0017(8) O23 0.0225(10) 0.0219(10) 0.0276(10) 0.0015(8) 0.0044(8) 0.0011(8) C11 0.0251(15) 0.0222(13) 0.0224(14) 0.0038(11) 0.0020(11) 0.0011(11) C12 0.0249(15) 0.0241(14) 0.0212(14) 0.0041(11) 0.0019(11) -0.0011(11) C13 0.0256(15) 0.0323(16) 0.0284(16) 0.0006(13) 0.0026(12) 0.0051(13) C14 0.0376(17) 0.0329(16) 0.0226(15) -0.0069(13) 0.0032(13) 0.0048(14) C15 0.0394(18) 0.0317(16) 0.0301(17) -0.0071(13) -0.0016(14) 0.0005(14) C16 0.0364(18) 0.0325(17) 0.0370(18) -0.0054(14) -0.0101(14) -0.0027(13) C17 0.0235(16) 0.0328(16) 0.0380(17) 0.0049(14) -0.0020(13) -0.0034(13) C18 0.0249(15) 0.0257(15) 0.0295(15) 0.0024(12) 0.0004(12) -0.0001(12) C19 0.0263(15) 0.0190(13) 0.0237(14) 0.0048(11) -0.0004(11) -0.0003(11) C20 0.0313(16) 0.0242(14) 0.0250(15) 0.0010(12) -0.0020(13) 0.0005(12) C24 0.0246(15) 0.0280(15) 0.0262(15) 0.0061(12) 0.0008(12) -0.0024(12) O25 0.0262(11) 0.0395(11) 0.0236(10) -0.0039(9) -0.0018(9) 0.0022(9) O26 0.0271(11) 0.0464(13) 0.0323(12) -0.0043(10) -0.0015(9) 0.0098(10) C31 0.0198(14) 0.0312(15) 0.0209(14) -0.0039(11) 0.0036(11) -0.0043(12) C32 0.0283(16) 0.0256(15) 0.0285(15) -0.0068(12) 0.0070(12) -0.0023(12) C33 0.0359(17) 0.0341(17) 0.0331(16) -0.0153(14) 0.0078(14) -0.0102(15) C34 0.0321(18) 0.055(2) 0.0287(16) -0.0159(15) -0.0021(14) -0.0089(16) C35 0.0284(16) 0.049(2) 0.0308(17) -0.0016(14) -0.0029(13) 0.0040(15) C36 0.0232(15) 0.0291(15) 0.0289(15) -0.0040(12) 0.0003(12) -0.0003(12) C37 0.0218(14) 0.0202(13) 0.0238(14) -0.0029(11) 0.0018(11) -0.0005(11) N38 0.0168(11) 0.0219(11) 0.0260(12) 0.0003(9) 0.0020(9) 0.0010(9) C39 0.0175(14) 0.0253(14) 0.0285(15) -0.0040(12) -0.0022(11) -0.0019(11) C40 0.0382(18) 0.0358(18) 0.0346(17) 0.0006(13) 0.0081(14) 0.0106(14) C41 0.046(2) 0.0277(17) 0.057(2) -0.0020(15) 0.0103(17) 0.0097(15) C42 0.038(2) 0.052(2) 0.044(2) -0.0261(17) 0.0081(16) 0.0033(17) C43 0.065(3) 0.071(3) 0.0284(18) -0.0084(17) 0.0042(18) 0.020(2) C44 0.045(2) 0.0437(19) 0.0307(17) 0.0016(15) 0.0036(15) 0.0111(16) C45 0.0175(13) 0.0222(13) 0.0242(14) -0.0011(11) -0.0010(11) -0.0020(11) N46 0.0182(11) 0.0254(12) 0.0255(12) -0.0044(10) 0.0028(10) 0.0008(9) O51 0.107(3) 0.0510(17) 0.0636(18) -0.0003(14) -0.0107(18) -0.0149(17) C52 0.113(5) 0.103(4) 0.095(4) 0.049(4) -0.040(4) -0.057(4) C53 0.136(6) 0.091(4) 0.124(5) -0.040(4) -0.007(5) -0.010(4) C54 0.100(5) 0.155(6) 0.096(4) 0.029(4) -0.038(4) -0.036(4) C55 0.085(4) 0.081(3) 0.084(3) -0.026(3) -0.032(3) 0.020(3) C56 0.116(5) 0.116(5) 0.143(6) 0.063(4) -0.024(5) -0.065(4) O61 0.0336(13) 0.0351(12) 0.0435(13) 0.0069(11) 0.0104(11) 0.0024(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.376(4) . ? C1 C9 1.434(4) . ? C1 C11 1.509(4) . ? C2 C3 1.411(4) . ? C2 C21 1.511(4) . ? C3 C4 1.364(4) . ? C4 C10 1.423(4) . ? C5 C6 1.354(5) . ? C5 C10 1.420(4) . ? C6 C7 1.402(5) . ? C7 C8 1.365(4) . ? C8 C9 1.415(4) . ? C9 C10 1.413(4) . ? C21 O23 1.252(3) . ? C21 O22 1.264(3) . ? C11 C12 1.378(4) . ? C11 C19 1.431(4) . ? C12 C13 1.419(4) . ? C12 C24 1.526(4) . ? C13 C14 1.346(4) . ? C14 C20 1.413(4) . ? C15 C16 1.362(5) . ? C15 C20 1.417(4) . ? C16 C17 1.400(4) . ? C17 C18 1.356(4) . ? C18 C19 1.428(4) . ? C19 C20 1.418(4) . ? C24 O26 1.256(3) . ? C24 O25 1.263(3) . ? C31 C36 1.386(4) . ? C31 C32 1.402(4) . ? C31 C37 1.511(4) . ? C32 C33 1.383(4) . ? C33 C34 1.392(5) . ? C34 C35 1.374(5) . ? C35 C36 1.393(4) . ? C37 N38 1.502(3) . ? C37 C45 1.547(4) . ? C39 C44 1.372(4) . ? C39 C40 1.390(4) . ? C39 C45 1.508(4) . ? C40 C41 1.378(4) . ? C41 C42 1.381(5) . ? C42 C43 1.360(5) . ? C43 C44 1.384(5) . ? C45 N46 1.500(3) . ? O51 C52 1.401(4) . ? C52 C54 1.512(4) . ? C52 C53 1.566(4) . ? C54 C56 1.535(4) . ? C54 C55 1.544(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 C2 C1 C9 118.8(2) . . ? C2 C1 C11 121.9(2) . . ? C9 C1 C11 119.2(2) . . ? C1 C2 C3 121.5(2) . . ? C1 C2 C21 120.8(2) . . ? C3 C2 C21 117.7(2) . . ? C4 C3 C2 120.4(3) . . ? C3 C4 C10 120.0(3) . . ? C6 C5 C10 120.8(3) . . ? C5 C6 C7 120.2(3) . . ? C8 C7 C6 120.5(3) . . ? C7 C8 C9 120.9(3) . . ? C10 C9 C8 118.4(3) . . ? C10 C9 C1 119.3(2) . . ? C8 C9 C1 122.3(3) . . ? C9 C10 C5 119.1(3) . . ? C9 C10 C4 119.7(2) . . ? C5 C10 C4 121.2(3) . . ? O23 C21 O22 124.8(2) . . ? O23 C21 C2 118.0(2) . . ? O22 C21 C2 117.2(2) . . ? C12 C11 C19 119.3(2) . . ? C12 C11 C1 122.5(2) . . ? C19 C11 C1 118.1(2) . . ? C11 C12 C13 119.8(3) . . ? C11 C12 C24 122.5(2) . . ? C13 C12 C24 117.4(2) . . ? C14 C13 C12 121.4(3) . . ? C13 C14 C20 121.0(3) . . ? C16 C15 C20 120.9(3) . . ? C15 C16 C17 119.9(3) . . ? C18 C17 C16 121.0(3) . . ? C17 C18 C19 121.0(3) . . ? C20 C19 C18 117.7(3) . . ? C20 C19 C11 119.9(2) . . ? C18 C19 C11 122.5(2) . . ? C14 C20 C15 122.0(3) . . ? C14 C20 C19 118.5(3) . . ? C15 C20 C19 119.5(3) . . ? O26 C24 O25 123.3(3) . . ? O26 C24 C12 117.8(2) . . ? O25 C24 C12 118.8(2) . . ? C36 C31 C32 119.8(3) . . ? C36 C31 C37 121.5(2) . . ? C32 C31 C37 118.7(3) . . ? C33 C32 C31 119.8(3) . . ? C32 C33 C34 119.9(3) . . ? C35 C34 C33 120.4(3) . . ? C34 C35 C36 120.2(3) . . ? C31 C36 C35 119.8(3) . . ? N38 C37 C31 110.5(2) . . ? N38 C37 C45 111.0(2) . . ? C31 C37 C45 110.0(2) . . ? C44 C39 C40 118.9(3) . . ? C44 C39 C45 119.7(3) . . ? C40 C39 C45 121.4(3) . . ? C41 C40 C39 119.5(3) . . ? C40 C41 C42 121.1(3) . . ? C43 C42 C41 119.2(3) . . ? C42 C43 C44 120.2(3) . . ? C39 C44 C43 121.0(3) . . ? N46 C45 C39 110.5(2) . . ? N46 C45 C37 111.7(2) . . ? C39 C45 C37 109.8(2) . . ? O51 C52 C54 113.1(4) . . ? O51 C52 C53 104.0(4) . . ? C54 C52 C53 110.6(4) . . ? C52 C54 C56 108.3(4) . . ? C52 C54 C55 102.4(4) . . ? C56 C54 C55 119.0(5) . . ? _diffrn_measured_fraction_theta_max 0.975 _diffrn_reflns_theta_full 27.87 _diffrn_measured_fraction_theta_full 0.975 _refine_diff_density_max 0.674 _refine_diff_density_min -0.369 _refine_diff_density_rms 0.056 #===END data_imai5_4 _database_code_depnum_ccdc_archive 'CCDC 287391' #data_ima572a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C41 H44 N2 O6' _chemical_formula_weight 660.78 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 9.5768(8) _cell_length_b 18.6287(16) _cell_length_c 19.5140(17) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3481.4(5) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9999 _cell_measurement_theta_min 1.51 _cell_measurement_theta_max 27.95 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.261 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1408 _exptl_absorpt_coefficient_mu 0.084 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9591 _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 'Bruker APEX' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 21530 _diffrn_reflns_av_R_equivalents 0.0534 _diffrn_reflns_av_sigmaI/netI 0.0742 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.51 _diffrn_reflns_theta_max 27.95 _reflns_number_total 7857 _reflns_number_gt 6317 _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 ; Two 2-pentanols of different chirality (from O62 to C65 and from O72 to C75) share the same site. Their occupancies were refined. The positions of the hydrogens attached to O62 nad O72 were not assigned. 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^)+(0.0857P)^2^+2.3337P] 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 -0.1(14) _refine_ls_number_reflns 7857 _refine_ls_number_parameters 443 _refine_ls_number_restraints 10 _refine_ls_R_factor_all 0.0898 _refine_ls_R_factor_gt 0.0715 _refine_ls_wR_factor_ref 0.1764 _refine_ls_wR_factor_gt 0.1652 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.037 _refine_ls_shift/su_max 0.016 _refine_ls_shift/su_mean 0.005 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 0.9492(3) 0.94494(16) 0.92096(15) 0.0134(6) Uani 1 1 d . . . C2 C 0.8886(3) 0.91063(16) 0.97529(15) 0.0138(6) Uani 1 1 d . . . C3 C 0.8410(3) 0.94933(17) 1.03274(17) 0.0193(7) Uani 1 1 d . . . H3 H 0.7977 0.9249 1.0685 0.023 Uiso 1 1 calc R . . C4 C 0.8571(4) 1.02171(18) 1.03693(18) 0.0236(7) Uani 1 1 d . . . H4 H 0.8303 1.0461 1.0764 0.028 Uiso 1 1 calc R . . C5 C 0.9292(4) 1.13513(18) 0.98330(19) 0.0276(8) Uani 1 1 d . . . H5 H 0.9033 1.1601 1.0225 0.033 Uiso 1 1 calc R . . C6 C 0.9808(4) 1.17129(19) 0.9285(2) 0.0322(9) Uani 1 1 d . . . H6 H 0.9897 1.2210 0.9304 0.039 Uiso 1 1 calc R . . C7 C 1.0208(4) 1.13448(18) 0.86884(19) 0.0261(8) Uani 1 1 d . . . H7 H 1.0543 1.1600 0.8313 0.031 Uiso 1 1 calc R . . C8 C 1.0109(4) 1.06152(17) 0.86572(17) 0.0201(7) Uani 1 1 d . . . H8 H 1.0386 1.0377 0.8261 0.024 Uiso 1 1 calc R . . C9 C 0.9591(3) 1.02160(17) 0.92163(16) 0.0166(6) Uani 1 1 d . . . C10 C 0.9148(4) 1.05955(17) 0.98102(18) 0.0210(7) Uani 1 1 d . . . C11 C 0.9955(3) 0.90528(15) 0.85810(15) 0.0141(6) Uani 1 1 d . . . C12 C 1.1338(3) 0.88998(16) 0.84442(16) 0.0161(6) Uani 1 1 d . . . C13 C 1.1715(4) 0.85733(17) 0.78182(17) 0.0206(7) Uani 1 1 d . . . H13 H 1.2652 0.8482 0.7729 0.025 Uiso 1 1 calc R . . C14 C 1.0743(4) 0.83888(17) 0.73442(17) 0.0204(7) Uani 1 1 d . . . H14 H 1.1023 0.8195 0.6927 0.024 Uiso 1 1 calc R . . C15 C 0.8260(4) 0.82549(18) 0.70232(18) 0.0243(8) Uani 1 1 d . . . H15 H 0.8520 0.8048 0.6609 0.029 Uiso 1 1 calc R . . C16 C 0.6878(4) 0.83246(19) 0.71747(18) 0.0270(8) Uani 1 1 d . . . H16 H 0.6205 0.8161 0.6869 0.032 Uiso 1 1 calc R . . C17 C 0.6475(4) 0.86458(18) 0.77957(18) 0.0242(8) Uani 1 1 d . . . H17 H 0.5533 0.8687 0.7903 0.029 Uiso 1 1 calc R . . C18 C 0.7461(3) 0.88992(16) 0.82444(17) 0.0178(7) Uani 1 1 d . . . H18 H 0.7178 0.9124 0.8646 0.021 Uiso 1 1 calc R . . C19 C 0.8902(3) 0.88232(16) 0.81043(16) 0.0156(6) Uani 1 1 d . . . C20 C 0.9303(4) 0.84895(16) 0.74808(17) 0.0182(7) Uani 1 1 d . . . C21 C 0.8707(3) 0.83069(16) 0.97574(15) 0.0138(6) Uani 1 1 d . . . O22 O 0.9701(2) 0.79319(11) 0.95333(11) 0.0160(5) Uani 1 1 d . . . O23 O 0.7595(2) 0.80539(11) 1.00003(11) 0.0170(5) Uani 1 1 d . . . C24 C 1.2471(3) 0.89915(16) 0.89759(16) 0.0165(6) Uani 1 1 d . . . O25 O 1.2227(2) 0.93543(12) 0.95031(11) 0.0186(5) Uani 1 1 d . . . O26 O 1.3608(3) 0.86701(13) 0.88720(12) 0.0261(6) Uani 1 1 d . . . C31 C 1.2209(3) 0.89481(17) 1.15758(16) 0.0153(6) Uani 1 1 d . . . C32 C 1.2251(4) 0.87714(19) 1.22631(18) 0.0264(8) Uani 1 1 d . . . H32 H 1.2666 0.8344 1.2401 0.032 Uiso 1 1 calc R . . C33 C 1.1686(4) 0.9223(2) 1.2744(2) 0.0357(10) Uani 1 1 d . . . H33 H 1.1746 0.9103 1.3206 0.043 Uiso 1 1 calc R . . C34 C 1.1037(4) 0.9844(2) 1.2556(2) 0.0338(9) Uani 1 1 d . . . H34 H 1.0649 1.0145 1.2886 0.041 Uiso 1 1 calc R . . C35 C 1.0963(4) 1.0022(2) 1.1866(2) 0.0338(9) Uani 1 1 d . . . H35 H 1.0511 1.0441 1.1731 0.041 Uiso 1 1 calc R . . C36 C 1.1560(4) 0.95780(19) 1.13790(17) 0.0236(7) Uani 1 1 d . . . H36 H 1.1525 0.9704 1.0918 0.028 Uiso 1 1 calc R . . C37 C 1.2912(3) 0.84681(16) 1.10590(15) 0.0138(6) Uani 1 1 d . . . H37 H 1.3213 0.8029 1.1292 0.017 Uiso 1 1 calc R . . N38 N 1.1915(3) 0.82671(14) 1.05023(13) 0.0146(5) Uani 1 1 d . . . H38A H 1.2344 0.7983 1.0202 0.022 Uiso 1 1 calc R . . H38B H 1.1619 0.8662 1.0291 0.022 Uiso 1 1 calc R . . H38C H 1.1189 0.8036 1.0682 0.022 Uiso 1 1 calc R . . C39 C 1.5311(3) 0.89268(17) 1.13219(15) 0.0153(6) Uani 1 1 d . . . C40 C 1.5727(3) 0.96048(16) 1.15376(16) 0.0180(7) Uani 1 1 d . . . H40 H 1.5299 1.0010 1.1355 0.022 Uiso 1 1 calc R . . C41 C 1.6775(4) 0.96827(18) 1.20236(16) 0.0202(7) Uani 1 1 d . . . H41 H 1.7057 1.0138 1.2161 0.024 Uiso 1 1 calc R . . C42 C 1.7400(3) 0.90795(18) 1.23033(16) 0.0197(7) Uani 1 1 d . . . H42 H 1.8106 0.9128 1.2627 0.024 Uiso 1 1 calc R . . C43 C 1.6972(4) 0.84076(18) 1.20997(17) 0.0211(7) Uani 1 1 d . . . H43 H 1.7378 0.8003 1.2295 0.025 Uiso 1 1 calc R . . C44 C 1.5946(3) 0.83273(18) 1.16100(16) 0.0174(6) Uani 1 1 d . . . H44 H 1.5677 0.7870 1.1472 0.021 Uiso 1 1 calc R . . C45 C 1.4219(3) 0.88539(16) 1.07733(16) 0.0141(6) Uani 1 1 d . . . H45 H 1.3946 0.9335 1.0622 0.017 Uiso 1 1 calc R . . N46 N 1.4812(3) 0.84578(13) 1.01732(12) 0.0131(5) Uani 1 1 d . . . H46A H 1.4163 0.8418 0.9849 0.020 Uiso 1 1 calc R . . H46B H 1.5083 0.8022 1.0305 0.020 Uiso 1 1 calc R . . H46C H 1.5542 0.8698 1.0008 0.020 Uiso 1 1 calc R . . O51 O 0.4630(3) 0.72763(15) 0.87531(14) 0.0267(6) Uani 1 1 d . . . O62 O 0.4385(10) 0.0236(4) 0.9779(4) 0.084(2) Uiso 0.707(12) 1 d PD A 1 C61 C 0.3733(15) 0.1204(7) 1.0399(7) 0.118(5) Uiso 0.707(12) 1 d PD A 1 H61A H 0.2894 0.0969 1.0549 0.177 Uiso 0.707(12) 1 calc PR A 1 H61B H 0.3593 0.1714 1.0404 0.177 Uiso 0.707(12) 1 calc PR A 1 H61C H 0.4486 0.1082 1.0702 0.177 Uiso 0.707(12) 1 calc PR A 1 C62 C 0.4072(14) 0.0973(6) 0.9709(6) 0.099(4) Uiso 0.707(12) 1 d PD A 1 H62 H 0.3245 0.1027 0.9418 0.119 Uiso 0.707(12) 1 calc PR A 1 C63 C 0.5396(18) 0.1342(7) 0.9335(9) 0.138(7) Uiso 0.707(12) 1 d PD A 1 H63A H 0.6194 0.1307 0.9640 0.166 Uiso 0.707(12) 1 calc PR A 1 H63B H 0.5612 0.1066 0.8927 0.166 Uiso 0.707(12) 1 calc PR A 1 C64 C 0.5249(13) 0.2017(5) 0.9157(6) 0.084(3) Uiso 0.707(12) 1 d PD A 1 H64A H 0.5448 0.2313 0.9554 0.101 Uiso 0.707(12) 1 calc PR A 1 H64B H 0.4279 0.2095 0.9034 0.101 Uiso 0.707(12) 1 calc PR A 1 C65 C 0.6101(12) 0.2257(6) 0.8603(5) 0.073(3) Uiso 0.707(12) 1 d PD A 1 H65A H 0.5953 0.2761 0.8531 0.110 Uiso 0.707(12) 1 calc PR A 1 H65B H 0.5859 0.1999 0.8194 0.110 Uiso 0.707(12) 1 calc PR A 1 H65C H 0.7066 0.2174 0.8711 0.110 Uiso 0.707(12) 1 calc PR A 1 O72 O 0.4991(13) 0.0031(5) 0.9660(5) 0.038(3) Uiso 0.293(12) 1 d PD A 2 C71 C 0.3708(18) 0.1052(11) 1.0092(12) 0.057(5) Uiso 0.293(12) 1 d PD A 2 H71A H 0.3428 0.0791 1.0493 0.086 Uiso 0.293(12) 1 calc PR A 2 H71B H 0.3022 0.0989 0.9738 0.086 Uiso 0.293(12) 1 calc PR A 2 H71C H 0.3791 0.1553 1.0201 0.086 Uiso 0.293(12) 1 calc PR A 2 C72 C 0.5047(16) 0.0783(6) 0.9854(7) 0.037(4) Uiso 0.293(12) 1 d PD A 2 H72 H 0.5730 0.0838 1.0225 0.045 Uiso 0.293(12) 1 calc PR A 2 C73 C 0.5593(12) 0.1212(5) 0.9204(6) 0.011(3) Uiso 0.293(12) 1 d PD A 2 H73A H 0.6460 0.0993 0.9053 0.014 Uiso 0.293(12) 1 calc PR A 2 H73B H 0.4919 0.1154 0.8837 0.014 Uiso 0.293(12) 1 calc PR A 2 C74 C 0.581(2) 0.1895(7) 0.9293(8) 0.045(4) Uiso 0.293(12) 1 d PD A 2 H74A H 0.6455 0.1937 0.9674 0.054 Uiso 0.293(12) 1 calc PR A 2 H74B H 0.4931 0.2097 0.9448 0.054 Uiso 0.293(12) 1 calc PR A 2 C75 C 0.6333(16) 0.2378(8) 0.8758(8) 0.026(4) Uiso 0.293(12) 1 d PD A 2 H75A H 0.6360 0.2861 0.8930 0.039 Uiso 0.293(12) 1 calc PR A 2 H75B H 0.5726 0.2357 0.8367 0.039 Uiso 0.293(12) 1 calc PR A 2 H75C H 0.7257 0.2233 0.8625 0.039 Uiso 0.293(12) 1 calc PR A 2 H51A H 0.431(5) 0.774(3) 0.880(2) 0.050 Uiso 1 1 d . . . H51B H 0.388(6) 0.708(3) 0.879(3) 0.050 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 0.0093(14) 0.0143(14) 0.0166(15) 0.0003(12) -0.0004(12) 0.0011(12) C2 0.0107(14) 0.0167(14) 0.0139(14) -0.0016(12) -0.0049(11) 0.0011(12) C3 0.0178(17) 0.0215(16) 0.0186(16) 0.0003(13) 0.0030(13) -0.0010(13) C4 0.0243(18) 0.0240(17) 0.0225(17) -0.0096(14) 0.0086(14) -0.0011(15) C5 0.0299(19) 0.0219(17) 0.031(2) -0.0095(15) 0.0064(16) -0.0024(16) C6 0.037(2) 0.0128(16) 0.046(2) 0.0026(16) 0.0028(19) -0.0018(16) C7 0.0260(19) 0.0212(16) 0.0309(19) 0.0051(15) -0.0013(16) -0.0030(15) C8 0.0217(17) 0.0198(15) 0.0189(16) 0.0027(13) -0.0041(14) 0.0006(14) C9 0.0127(15) 0.0167(15) 0.0203(16) 0.0006(13) -0.0027(13) 0.0024(12) C10 0.0195(17) 0.0160(15) 0.0275(18) -0.0053(14) -0.0013(14) 0.0004(13) C11 0.0186(15) 0.0116(13) 0.0122(14) 0.0036(12) 0.0006(12) -0.0017(13) C12 0.0182(15) 0.0137(14) 0.0163(15) 0.0048(12) 0.0002(13) 0.0005(12) C13 0.0202(17) 0.0187(15) 0.0230(17) 0.0014(13) 0.0039(14) 0.0034(13) C14 0.0233(17) 0.0207(15) 0.0172(16) -0.0019(13) 0.0005(14) 0.0021(14) C15 0.035(2) 0.0185(16) 0.0194(17) -0.0028(14) -0.0028(15) -0.0046(15) C16 0.028(2) 0.0248(17) 0.0278(19) 0.0018(15) -0.0095(15) -0.0087(15) C17 0.0192(17) 0.0275(18) 0.0259(18) 0.0095(15) -0.0045(14) -0.0054(15) C18 0.0179(16) 0.0156(14) 0.0199(16) 0.0038(12) 0.0009(13) 0.0004(13) C19 0.0162(16) 0.0136(14) 0.0171(15) 0.0060(12) -0.0006(12) -0.0011(12) C20 0.0205(16) 0.0141(14) 0.0201(16) 0.0036(13) -0.0025(13) 0.0010(13) C21 0.0152(15) 0.0154(14) 0.0109(14) 0.0000(12) -0.0045(12) -0.0034(12) O22 0.0153(11) 0.0158(11) 0.0170(11) 0.0009(9) 0.0021(9) 0.0016(9) O23 0.0130(11) 0.0163(10) 0.0217(11) -0.0009(9) 0.0017(9) 0.0004(9) C24 0.0174(16) 0.0173(14) 0.0149(15) 0.0091(13) 0.0027(12) 0.0021(13) O25 0.0167(12) 0.0241(11) 0.0149(11) -0.0013(9) -0.0020(9) 0.0022(9) O26 0.0194(12) 0.0369(14) 0.0218(12) -0.0011(11) -0.0026(10) 0.0125(11) C31 0.0098(14) 0.0198(15) 0.0162(15) -0.0024(12) -0.0019(12) -0.0046(12) C32 0.032(2) 0.0273(17) 0.0194(17) 0.0005(14) 0.0022(15) -0.0003(16) C33 0.038(2) 0.051(2) 0.0177(17) -0.0081(17) 0.0077(16) -0.012(2) C34 0.025(2) 0.046(2) 0.031(2) -0.0229(18) 0.0056(16) -0.0082(18) C35 0.026(2) 0.032(2) 0.044(2) -0.0154(18) -0.0040(18) 0.0088(16) C36 0.0226(18) 0.0303(18) 0.0178(16) -0.0071(14) -0.0014(14) 0.0032(15) C37 0.0120(15) 0.0145(14) 0.0150(14) 0.0009(12) -0.0023(12) -0.0015(12) N38 0.0136(12) 0.0145(12) 0.0158(13) -0.0022(10) 0.0008(10) 0.0016(10) C39 0.0121(15) 0.0193(15) 0.0144(14) -0.0027(12) 0.0048(12) -0.0007(12) C40 0.0198(16) 0.0170(15) 0.0172(15) -0.0016(13) 0.0050(13) 0.0004(13) C41 0.0224(17) 0.0198(16) 0.0182(16) -0.0095(13) 0.0027(13) -0.0041(14) C42 0.0156(16) 0.0318(17) 0.0118(14) -0.0074(13) -0.0028(12) -0.0021(14) C43 0.0193(17) 0.0243(16) 0.0199(16) 0.0010(14) -0.0034(13) 0.0033(14) C44 0.0141(15) 0.0198(15) 0.0182(15) -0.0019(13) -0.0002(13) -0.0044(13) C45 0.0108(14) 0.0130(14) 0.0186(15) -0.0004(12) 0.0021(12) -0.0017(12) N46 0.0114(12) 0.0145(12) 0.0134(12) -0.0002(10) -0.0025(10) -0.0009(10) O51 0.0211(14) 0.0276(14) 0.0313(14) 0.0040(11) -0.0062(11) -0.0026(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.368(4) . ? C1 C9 1.431(4) . ? C1 C11 1.499(4) . ? C2 C3 1.409(4) . ? C2 C21 1.499(4) . ? C3 C4 1.360(5) . ? C4 C10 1.412(5) . ? C5 C6 1.357(5) . ? C5 C10 1.415(5) . ? C6 C7 1.404(5) . ? C7 C8 1.364(5) . ? C8 C9 1.411(5) . ? C9 C10 1.422(5) . ? C11 C12 1.381(5) . ? C11 C19 1.437(4) . ? C12 C13 1.411(5) . ? C12 C24 1.511(5) . ? C13 C14 1.357(5) . ? C14 C20 1.416(5) . ? C15 C16 1.362(5) . ? C15 C20 1.410(5) . ? C16 C17 1.406(5) . ? C17 C18 1.371(5) . ? C18 C19 1.414(5) . ? C19 C20 1.419(5) . ? C21 O23 1.257(4) . ? C21 O22 1.259(4) . ? C24 O25 1.253(4) . ? C24 O26 1.259(4) . ? C31 C32 1.382(5) . ? C31 C36 1.382(5) . ? C31 C37 1.507(4) . ? C32 C33 1.371(5) . ? C33 C34 1.365(6) . ? C34 C35 1.389(6) . ? C35 C36 1.384(5) . ? C37 N38 1.494(4) . ? C37 C45 1.548(4) . ? C39 C40 1.389(4) . ? C39 C44 1.390(5) . ? C39 C45 1.503(4) . ? C40 C41 1.389(5) . ? C41 C42 1.385(5) . ? C42 C43 1.376(5) . ? C43 C44 1.378(5) . ? C45 N46 1.496(4) . ? O62 C62 1.411(12) . ? C61 C62 1.451(15) . ? C62 C63 1.617(15) . ? C63 C64 1.311(12) . ? C64 C65 1.427(11) . ? O72 C72 1.452(14) . ? C71 C72 1.452(17) . ? C72 C73 1.588(14) . ? C73 C74 1.302(14) . ? C74 C75 1.466(14) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C9 119.2(3) . . ? C2 C1 C11 122.0(3) . . ? C9 C1 C11 118.7(3) . . ? C1 C2 C3 121.0(3) . . ? C1 C2 C21 121.2(3) . . ? C3 C2 C21 117.8(3) . . ? C4 C3 C2 121.3(3) . . ? C3 C4 C10 119.5(3) . . ? C6 C5 C10 120.3(3) . . ? C5 C6 C7 120.7(3) . . ? C8 C7 C6 120.3(3) . . ? C7 C8 C9 121.0(3) . . ? C8 C9 C10 118.2(3) . . ? C8 C9 C1 122.8(3) . . ? C10 C9 C1 118.9(3) . . ? C4 C10 C5 120.7(3) . . ? C4 C10 C9 119.9(3) . . ? C5 C10 C9 119.4(3) . . ? C12 C11 C19 119.1(3) . . ? C12 C11 C1 122.9(3) . . ? C19 C11 C1 117.9(3) . . ? C11 C12 C13 120.1(3) . . ? C11 C12 C24 122.2(3) . . ? C13 C12 C24 117.4(3) . . ? C14 C13 C12 121.6(3) . . ? C13 C14 C20 120.4(3) . . ? C16 C15 C20 121.4(3) . . ? C15 C16 C17 119.6(3) . . ? C18 C17 C16 120.5(3) . . ? C17 C18 C19 120.9(3) . . ? C18 C19 C20 118.3(3) . . ? C18 C19 C11 122.0(3) . . ? C20 C19 C11 119.7(3) . . ? C15 C20 C14 122.0(3) . . ? C15 C20 C19 119.1(3) . . ? C14 C20 C19 118.9(3) . . ? O23 C21 O22 124.3(3) . . ? O23 C21 C2 118.1(3) . . ? O22 C21 C2 117.6(3) . . ? O25 C24 O26 123.4(3) . . ? O25 C24 C12 119.4(3) . . ? O26 C24 C12 117.2(3) . . ? C32 C31 C36 119.0(3) . . ? C32 C31 C37 119.7(3) . . ? C36 C31 C37 121.3(3) . . ? C33 C32 C31 120.4(4) . . ? C34 C33 C32 121.1(4) . . ? C33 C34 C35 119.1(3) . . ? C36 C35 C34 120.1(4) . . ? C31 C36 C35 120.2(3) . . ? N38 C37 C31 110.5(2) . . ? N38 C37 C45 111.8(2) . . ? C31 C37 C45 109.1(2) . . ? C40 C39 C44 118.9(3) . . ? C40 C39 C45 119.8(3) . . ? C44 C39 C45 121.3(3) . . ? C41 C40 C39 120.6(3) . . ? C42 C41 C40 119.8(3) . . ? C43 C42 C41 119.7(3) . . ? C42 C43 C44 120.8(3) . . ? C43 C44 C39 120.3(3) . . ? N46 C45 C39 109.8(2) . . ? N46 C45 C37 111.1(2) . . ? C39 C45 C37 110.4(2) . . ? O62 C62 C61 104.3(10) . . ? O62 C62 C63 106.9(10) . . ? C61 C62 C63 117.9(12) . . ? C64 C63 C62 116.3(13) . . ? C63 C64 C65 116.1(11) . . ? O72 C72 C71 112.5(13) . . ? O72 C72 C73 106.8(10) . . ? C71 C72 C73 111.9(13) . . ? C74 C73 C72 115.9(11) . . ? C73 C74 C75 124.0(14) . . ? _diffrn_measured_fraction_theta_max 0.973 _diffrn_reflns_theta_full 27.95 _diffrn_measured_fraction_theta_full 0.973 _refine_diff_density_max 0.851 _refine_diff_density_min -0.376 _refine_diff_density_rms 0.068 #===END data_imai5_5 _database_code_depnum_ccdc_archive 'CCDC 287392' #data_ima5d4b _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C42 H46 N2 O6' _chemical_formula_weight 674.81 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+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 9.6692(5) _cell_length_b 18.7489(11) _cell_length_c 19.8331(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3595.5(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9999 _cell_measurement_theta_min 1.49 _cell_measurement_theta_max 27.90 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.247 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1440 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9558 _exptl_absorpt_correction_T_max 0.9917 _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 'Bruker APEX' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 22550 _diffrn_reflns_av_R_equivalents 0.0504 _diffrn_reflns_av_sigmaI/netI 0.0676 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 1.49 _diffrn_reflns_theta_max 27.90 _reflns_number_total 8229 _reflns_number_gt 6793 _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 ; Two 2-hexanols of different chirality (from C41 to O42 and from C51 and O52) share the same site. Their occupancies were refined. The positions of the hydrogens attached to O42 and O52 were not assigned. 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^)+(0.0680P)^2^+1.3412P] 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 -0.2(12) _refine_ls_number_reflns 8229 _refine_ls_number_parameters 453 _refine_ls_number_restraints 12 _refine_ls_R_factor_all 0.0789 _refine_ls_R_factor_gt 0.0631 _refine_ls_wR_factor_ref 0.1528 _refine_ls_wR_factor_gt 0.1432 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_restrained_S_all 1.069 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.5081(3) 0.90471(13) 0.63946(12) 0.0176(5) Uani 1 1 d . . . C2 C 0.3716(3) 0.88747(13) 0.65276(13) 0.0199(5) Uani 1 1 d . . . C3 C 0.3348(3) 0.85474(14) 0.71462(13) 0.0247(6) Uani 1 1 d . . . H3 H 0.2423 0.8451 0.7235 0.030 Uiso 1 1 calc R . . C4 C 0.4319(3) 0.83716(15) 0.76112(14) 0.0281(6) Uani 1 1 d . . . H4 H 0.4050 0.8174 0.8021 0.034 Uiso 1 1 calc R . . C5 C 0.5735(3) 0.84868(14) 0.74758(14) 0.0243(6) Uani 1 1 d . . . C6 C 0.6784(3) 0.82645(16) 0.79357(15) 0.0313(7) Uani 1 1 d . . . H6 H 0.6536 0.8055 0.8343 0.038 Uiso 1 1 calc R . . C7 C 0.8135(3) 0.83554(17) 0.77857(16) 0.0355(7) Uani 1 1 d . . . H7 H 0.8805 0.8197 0.8087 0.043 Uiso 1 1 calc R . . C8 C 0.8540(3) 0.86839(15) 0.71859(15) 0.0304(7) Uani 1 1 d . . . H8 H 0.9475 0.8739 0.7088 0.036 Uiso 1 1 calc R . . C9 C 0.7558(3) 0.89259(14) 0.67400(14) 0.0232(6) Uani 1 1 d . . . H9 H 0.7835 0.9157 0.6348 0.028 Uiso 1 1 calc R . . C10 C 0.6132(3) 0.88278(13) 0.68692(13) 0.0201(5) Uani 1 1 d . . . C11 C 0.2597(3) 0.89625(14) 0.60078(13) 0.0223(5) Uani 1 1 d . . . C12 C 0.5528(3) 0.94479(14) 0.57861(13) 0.0193(5) Uani 1 1 d . . . C13 C 0.6130(2) 0.91161(14) 0.52404(13) 0.0194(5) Uani 1 1 d . . . C14 C 0.6557(3) 0.95142(15) 0.46704(14) 0.0244(6) Uani 1 1 d . . . H14 H 0.6975 0.9282 0.4310 0.029 Uiso 1 1 calc R . . C15 C 0.6365(3) 1.02307(15) 0.46441(14) 0.0284(6) Uani 1 1 d . . . H15 H 0.6612 1.0480 0.4257 0.034 Uiso 1 1 calc R . . C16 C 0.5793(3) 1.06016(15) 0.52000(15) 0.0286(6) Uani 1 1 d . . . C17 C 0.5625(4) 1.13533(16) 0.51988(18) 0.0393(8) Uani 1 1 d . . . H17 H 0.5856 1.1613 0.4815 0.047 Uiso 1 1 calc R . . C18 C 0.5131(4) 1.16982(16) 0.57497(18) 0.0409(8) Uani 1 1 d . . . H18 H 0.5030 1.2191 0.5742 0.049 Uiso 1 1 calc R . . C19 C 0.4774(3) 1.13153(16) 0.63287(17) 0.0364(7) Uani 1 1 d . . . H19 H 0.4447 1.1557 0.6705 0.044 Uiso 1 1 calc R . . C20 C 0.4900(3) 1.05907(15) 0.63479(15) 0.0284(6) Uani 1 1 d . . . H20 H 0.4651 1.0344 0.6737 0.034 Uiso 1 1 calc R . . C21 C 0.5402(3) 1.02127(14) 0.57884(14) 0.0229(6) Uani 1 1 d . . . C22 C 0.6324(3) 0.83240(14) 0.52304(12) 0.0193(5) Uani 1 1 d . . . C23 C 0.4188(3) 0.11635(14) 0.92470(13) 0.0189(5) Uani 1 1 d . . . H23 H 0.3895 0.0690 0.9400 0.023 Uiso 1 1 calc R . . C24 C 0.5286(3) 0.10701(14) 0.87115(13) 0.0200(5) Uani 1 1 d . . . C25 C 0.5654(3) 0.03891(15) 0.84985(14) 0.0253(6) Uani 1 1 d . . . H25 H 0.5207 -0.0006 0.8679 0.030 Uiso 1 1 calc R . . C26 C 0.6678(3) 0.02958(16) 0.80207(15) 0.0303(7) Uani 1 1 d . . . H26 H 0.6926 -0.0161 0.7885 0.036 Uiso 1 1 calc R . . C27 C 0.7333(3) 0.08818(17) 0.77440(14) 0.0310(7) Uani 1 1 d . . . H27 H 0.8023 0.0819 0.7423 0.037 Uiso 1 1 calc R . . C28 C 0.6963(3) 0.15597(17) 0.79438(14) 0.0285(6) Uani 1 1 d . . . H28 H 0.7398 0.1953 0.7753 0.034 Uiso 1 1 calc R . . C29 C 0.5945(3) 0.16582(15) 0.84290(13) 0.0232(6) Uani 1 1 d . . . H29 H 0.5705 0.2116 0.8565 0.028 Uiso 1 1 calc R . . C30 C 0.2921(3) 0.15522(14) 0.89505(13) 0.0192(5) Uani 1 1 d . . . H30 H 0.3241 0.1986 0.8724 0.023 Uiso 1 1 calc R . . C31 C 0.2230(3) 0.10782(14) 0.84338(13) 0.0213(5) Uani 1 1 d . . . C32 C 0.2280(3) 0.12609(17) 0.77628(15) 0.0334(7) Uani 1 1 d . . . H32 H 0.2687 0.1689 0.7634 0.040 Uiso 1 1 calc R . . C33 C 0.1729(4) 0.0812(2) 0.72773(17) 0.0433(8) Uani 1 1 d . . . H33 H 0.1795 0.0935 0.6824 0.052 Uiso 1 1 calc R . . C34 C 0.1087(3) 0.0190(2) 0.74590(17) 0.0413(8) Uani 1 1 d . . . H34 H 0.0702 -0.0105 0.7132 0.050 Uiso 1 1 calc R . . C35 C 0.1018(3) 0.00033(18) 0.81314(18) 0.0420(8) Uani 1 1 d . . . H35 H 0.0591 -0.0420 0.8259 0.050 Uiso 1 1 calc R . . C36 C 0.1585(3) 0.04477(17) 0.86178(16) 0.0338(7) Uani 1 1 d . . . H36 H 0.1531 0.0322 0.9071 0.041 Uiso 1 1 calc R . . N1 N 0.1910(2) 0.17602(12) 0.94906(11) 0.0202(5) Uani 1 1 d . . . H1A H 0.1092 0.1853 0.9305 0.030 Uiso 1 1 calc R . . H1B H 0.2217 0.2147 0.9703 0.030 Uiso 1 1 calc R . . H1C H 0.1824 0.1404 0.9784 0.030 Uiso 1 1 calc R . . N2 N 0.4771(2) 0.15614(11) 0.98389(10) 0.0185(4) Uani 1 1 d . . . H2A H 0.5668 0.1464 0.9879 0.028 Uiso 1 1 calc R . . H2B H 0.4331 0.1429 1.0213 0.028 Uiso 1 1 calc R . . H2C H 0.4659 0.2028 0.9776 0.028 Uiso 1 1 calc R . . O1 O 0.53510(18) 0.79419(9) 0.54439(9) 0.0213(4) Uani 1 1 d . . . O2 O 0.74421(19) 0.80814(9) 0.49934(10) 0.0236(4) Uani 1 1 d . . . O3 O 0.28556(19) 0.92965(10) 0.54728(9) 0.0240(4) Uani 1 1 d . . . O4 O 0.1456(2) 0.86575(11) 0.61157(10) 0.0314(5) Uani 1 1 d . . . O6 O 0.9602(2) 0.22839(13) 0.87663(11) 0.0333(5) Uani 1 1 d . . . C41 C -0.0209(7) 0.0250(3) 0.5604(3) 0.0469(16) Uiso 0.584(5) 1 d PD A 1 H41A H 0.0316 -0.0111 0.5834 0.070 Uiso 0.584(5) 1 calc PR A 1 H41B H -0.0687 0.0040 0.5229 0.070 Uiso 0.584(5) 1 calc PR A 1 H41C H -0.0868 0.0455 0.5909 0.070 Uiso 0.584(5) 1 calc PR A 1 C42 C 0.0747(6) 0.0819(3) 0.5354(3) 0.0293(13) Uiso 0.584(5) 1 d PD A 1 H42 H 0.1281 0.1000 0.5737 0.035 Uiso 0.584(5) 1 calc PR A 1 C43 C 0.0167(8) 0.1443(3) 0.4975(4) 0.0532(18) Uiso 0.584(5) 1 d PD A 1 H43A H -0.0281 0.1276 0.4567 0.064 Uiso 0.584(5) 1 calc PR A 1 H43B H 0.0913 0.1761 0.4846 0.064 Uiso 0.584(5) 1 calc PR A 1 C44 C -0.0888(7) 0.1855(4) 0.5409(3) 0.0512(17) Uiso 0.584(5) 1 d PD A 1 H44A H -0.1278 0.2238 0.5141 0.061 Uiso 0.584(5) 1 calc PR A 1 H44B H -0.1636 0.1535 0.5530 0.061 Uiso 0.584(5) 1 calc PR A 1 C45 C -0.0351(7) 0.2136(4) 0.5980(4) 0.0541(18) Uiso 0.584(5) 1 d PD A 1 H45A H 0.0388 0.2461 0.5859 0.065 Uiso 0.584(5) 1 calc PR A 1 H45B H 0.0052 0.1753 0.6245 0.065 Uiso 0.584(5) 1 calc PR A 1 C46 C -0.1387(8) 0.2533(4) 0.6417(4) 0.0464(17) Uiso 0.584(5) 1 d PD A 1 H46A H -0.0931 0.2710 0.6813 0.070 Uiso 0.584(5) 1 calc PR A 1 H46B H -0.2118 0.2215 0.6546 0.070 Uiso 0.584(5) 1 calc PR A 1 H46C H -0.1766 0.2926 0.6167 0.070 Uiso 0.584(5) 1 calc PR A 1 O42 O 0.1707(4) 0.0469(2) 0.4883(2) 0.0461(12) Uiso 0.584(5) 1 d PD A 1 C51 C 0.1537(16) 0.1198(8) 0.4569(7) 0.103(5) Uiso 0.416(5) 1 d PD A 2 H51A H 0.2449 0.1007 0.4505 0.154 Uiso 0.416(5) 1 calc PR A 2 H51B H 0.1572 0.1709 0.4545 0.154 Uiso 0.416(5) 1 calc PR A 2 H51C H 0.0935 0.1020 0.4222 0.154 Uiso 0.416(5) 1 calc PR A 2 C52 C 0.1008(13) 0.0980(6) 0.5234(7) 0.072(4) Uiso 0.416(5) 1 d PD A 2 H52 H 0.1635 0.1128 0.5596 0.086 Uiso 0.416(5) 1 calc PR A 2 C53 C -0.0449(15) 0.1307(8) 0.5327(7) 0.108(5) Uiso 0.416(5) 1 d PD A 2 H53A H -0.0443 0.1797 0.5168 0.129 Uiso 0.416(5) 1 calc PR A 2 H53B H -0.1110 0.1043 0.5057 0.129 Uiso 0.416(5) 1 calc PR A 2 C54 C -0.0874(13) 0.1295(6) 0.6013(6) 0.077(4) Uiso 0.416(5) 1 d PD A 2 H54A H -0.0385 0.0914 0.6243 0.092 Uiso 0.416(5) 1 calc PR A 2 H54B H -0.1854 0.1186 0.6031 0.092 Uiso 0.416(5) 1 calc PR A 2 C55 C -0.0613(18) 0.1995(7) 0.6387(8) 0.104(5) Uiso 0.416(5) 1 d PD A 2 H55A H 0.0361 0.2103 0.6333 0.125 Uiso 0.416(5) 1 calc PR A 2 H55B H -0.0756 0.1897 0.6862 0.125 Uiso 0.416(5) 1 calc PR A 2 C56 C -0.1448(19) 0.2721(8) 0.6221(9) 0.105(6) Uiso 0.416(5) 1 d PD A 2 H56A H -0.1123 0.3097 0.6509 0.157 Uiso 0.416(5) 1 calc PR A 2 H56B H -0.2418 0.2647 0.6297 0.157 Uiso 0.416(5) 1 calc PR A 2 H56C H -0.1299 0.2851 0.5758 0.157 Uiso 0.416(5) 1 calc PR A 2 O52 O 0.0673(9) 0.0220(4) 0.5284(4) 0.072(2) Uiso 0.416(5) 1 d PD A 2 H6B H 0.932(4) 0.274(2) 0.8752(19) 0.050 Uiso 1 1 d . . . H6A H 0.892(4) 0.202(2) 0.881(2) 0.050 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 0.0187(12) 0.0168(11) 0.0173(12) -0.0036(10) 0.0001(10) 0.0008(10) C2 0.0198(12) 0.0196(12) 0.0204(12) -0.0061(10) -0.0023(10) -0.0004(10) C3 0.0206(14) 0.0281(14) 0.0254(14) -0.0023(11) 0.0056(11) -0.0023(11) C4 0.0308(15) 0.0316(15) 0.0219(14) 0.0054(12) 0.0009(12) -0.0062(13) C5 0.0256(14) 0.0210(13) 0.0263(14) -0.0029(11) -0.0036(11) -0.0028(11) C6 0.0337(17) 0.0305(15) 0.0297(15) 0.0058(12) -0.0072(13) -0.0009(13) C7 0.0309(16) 0.0371(17) 0.0385(17) 0.0031(13) -0.0131(14) 0.0063(14) C8 0.0210(14) 0.0338(16) 0.0364(17) -0.0059(13) -0.0027(12) 0.0027(12) C9 0.0212(13) 0.0250(13) 0.0234(13) -0.0070(11) -0.0016(11) 0.0015(11) C10 0.0218(13) 0.0165(12) 0.0221(13) -0.0065(10) -0.0006(10) -0.0007(10) C11 0.0194(13) 0.0232(13) 0.0243(14) -0.0047(11) 0.0012(11) -0.0008(11) C12 0.0120(12) 0.0241(13) 0.0218(13) -0.0010(10) -0.0027(10) -0.0009(10) C13 0.0123(12) 0.0238(13) 0.0219(13) 0.0002(10) -0.0022(10) -0.0016(10) C14 0.0177(13) 0.0289(14) 0.0268(14) -0.0009(11) 0.0057(11) -0.0022(11) C15 0.0287(15) 0.0292(15) 0.0273(15) 0.0085(12) 0.0046(12) -0.0054(12) C16 0.0264(15) 0.0220(13) 0.0373(16) 0.0028(12) -0.0018(13) -0.0030(11) C17 0.0445(19) 0.0252(16) 0.048(2) 0.0098(14) 0.0004(16) -0.0019(14) C18 0.050(2) 0.0188(15) 0.054(2) -0.0024(14) 0.0015(17) 0.0009(14) C19 0.0372(18) 0.0284(15) 0.0435(19) -0.0125(14) 0.0021(15) 0.0013(13) C20 0.0293(16) 0.0262(14) 0.0296(15) -0.0030(12) -0.0038(12) -0.0014(12) C21 0.0194(13) 0.0223(13) 0.0270(14) 0.0001(11) -0.0031(11) -0.0021(10) C22 0.0151(12) 0.0247(13) 0.0180(12) -0.0020(10) -0.0046(10) -0.0010(10) C23 0.0142(12) 0.0212(13) 0.0213(13) 0.0004(10) -0.0017(10) -0.0007(10) C24 0.0143(12) 0.0241(13) 0.0215(13) -0.0032(10) -0.0046(10) 0.0009(10) C25 0.0203(14) 0.0251(14) 0.0307(15) -0.0040(11) -0.0054(11) 0.0008(11) C26 0.0278(15) 0.0320(16) 0.0312(15) -0.0124(12) -0.0067(12) 0.0100(13) C27 0.0195(14) 0.0507(18) 0.0229(14) -0.0136(13) 0.0031(11) 0.0055(13) C28 0.0205(14) 0.0408(17) 0.0242(14) 0.0000(12) 0.0043(11) -0.0025(12) C29 0.0197(13) 0.0273(14) 0.0227(13) -0.0008(11) 0.0010(10) 0.0024(11) C30 0.0153(12) 0.0201(12) 0.0222(13) -0.0004(10) 0.0015(10) 0.0001(10) C31 0.0124(12) 0.0263(13) 0.0252(14) -0.0023(11) -0.0003(10) 0.0020(10) C32 0.0312(16) 0.0389(17) 0.0299(16) 0.0005(13) -0.0031(13) -0.0025(13) C33 0.043(2) 0.062(2) 0.0249(16) -0.0070(15) -0.0018(14) -0.0012(17) C34 0.0286(17) 0.053(2) 0.0423(19) -0.0238(16) -0.0051(14) -0.0024(15) C35 0.0340(18) 0.0407(19) 0.051(2) -0.0096(16) -0.0059(16) -0.0115(14) C36 0.0298(16) 0.0404(17) 0.0312(16) -0.0045(13) -0.0010(13) -0.0080(13) N1 0.0130(10) 0.0237(11) 0.0240(11) -0.0009(9) 0.0004(9) 0.0006(8) N2 0.0130(10) 0.0216(11) 0.0208(11) 0.0014(8) 0.0017(8) -0.0003(8) O1 0.0154(9) 0.0208(9) 0.0278(10) -0.0012(7) 0.0035(8) -0.0024(7) O2 0.0144(9) 0.0247(9) 0.0317(10) 0.0002(8) 0.0044(8) 0.0005(7) O3 0.0196(9) 0.0288(10) 0.0237(10) 0.0025(8) -0.0015(8) 0.0002(7) O4 0.0199(10) 0.0443(12) 0.0300(11) 0.0023(9) -0.0046(8) -0.0113(9) O6 0.0289(12) 0.0345(12) 0.0364(12) 0.0041(10) -0.0084(9) -0.0019(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.384(4) . ? C1 C10 1.445(4) . ? C1 C12 1.486(4) . ? C2 C3 1.417(4) . ? C2 C11 1.504(4) . ? C3 C4 1.356(4) . ? C4 C5 1.412(4) . ? C5 C10 1.415(4) . ? C5 C6 1.427(4) . ? C6 C7 1.350(5) . ? C7 C8 1.396(4) . ? C8 C9 1.375(4) . ? C9 C10 1.415(4) . ? C11 O3 1.257(3) . ? C11 O4 1.260(3) . ? C12 C13 1.377(4) . ? C12 C21 1.439(4) . ? C13 C14 1.416(4) . ? C13 C22 1.497(4) . ? C14 C15 1.357(4) . ? C15 C16 1.416(4) . ? C16 C17 1.419(4) . ? C16 C21 1.427(4) . ? C17 C18 1.356(5) . ? C18 C19 1.398(5) . ? C19 C20 1.365(4) . ? C20 C21 1.403(4) . ? C22 O1 1.256(3) . ? C22 O2 1.263(3) . ? C23 N2 1.501(3) . ? C23 C24 1.512(4) . ? C23 C30 1.542(3) . ? C24 C25 1.391(4) . ? C24 C29 1.391(4) . ? C25 C26 1.382(4) . ? C26 C27 1.382(4) . ? C27 C28 1.379(4) . ? C28 C29 1.389(4) . ? C30 N1 1.501(3) . ? C30 C31 1.512(4) . ? C31 C32 1.375(4) . ? C31 C36 1.386(4) . ? C32 C33 1.385(4) . ? C33 C34 1.370(5) . ? C34 C35 1.380(5) . ? C35 C36 1.387(4) . ? C41 C42 1.496(8) . ? C42 O42 1.471(7) . ? C42 C43 1.500(8) . ? C43 C44 1.542(10) . ? C44 C45 1.352(9) . ? C45 C46 1.519(9) . ? C51 C52 1.473(14) . ? C52 O52 1.464(12) . ? C52 C53 1.549(14) . ? C53 C54 1.420(15) . ? C54 C55 1.529(14) . ? C55 C56 1.617(15) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C10 118.7(2) . . ? C2 C1 C12 123.4(2) . . ? C10 C1 C12 117.9(2) . . ? C1 C2 C3 120.4(2) . . ? C1 C2 C11 122.0(2) . . ? C3 C2 C11 117.4(2) . . ? C4 C3 C2 121.4(3) . . ? C3 C4 C5 120.3(3) . . ? C4 C5 C10 119.6(3) . . ? C4 C5 C6 121.6(3) . . ? C10 C5 C6 118.8(3) . . ? C7 C6 C5 120.7(3) . . ? C6 C7 C8 121.0(3) . . ? C9 C8 C7 120.0(3) . . ? C8 C9 C10 120.9(3) . . ? C9 C10 C5 118.5(2) . . ? C9 C10 C1 122.0(2) . . ? C5 C10 C1 119.4(2) . . ? O3 C11 O4 122.9(3) . . ? O3 C11 C2 119.3(2) . . ? O4 C11 C2 117.6(2) . . ? C13 C12 C21 119.2(2) . . ? C13 C12 C1 122.2(2) . . ? C21 C12 C1 118.4(2) . . ? C12 C13 C14 120.8(2) . . ? C12 C13 C22 120.8(2) . . ? C14 C13 C22 118.4(2) . . ? C15 C14 C13 120.8(3) . . ? C14 C15 C16 120.6(3) . . ? C15 C16 C17 122.1(3) . . ? C15 C16 C21 119.3(2) . . ? C17 C16 C21 118.6(3) . . ? C18 C17 C16 120.8(3) . . ? C17 C18 C19 120.3(3) . . ? C20 C19 C18 120.8(3) . . ? C19 C20 C21 120.8(3) . . ? C20 C21 C16 118.7(2) . . ? C20 C21 C12 122.4(2) . . ? C16 C21 C12 118.9(2) . . ? O1 C22 O2 124.1(2) . . ? O1 C22 C13 117.9(2) . . ? O2 C22 C13 118.0(2) . . ? N2 C23 C24 110.1(2) . . ? N2 C23 C30 111.2(2) . . ? C24 C23 C30 110.2(2) . . ? C25 C24 C29 119.2(2) . . ? C25 C24 C23 119.9(2) . . ? C29 C24 C23 120.9(2) . . ? C26 C25 C24 120.5(3) . . ? C25 C26 C27 120.0(3) . . ? C28 C27 C26 120.0(3) . . ? C27 C28 C29 120.4(3) . . ? C28 C29 C24 119.9(3) . . ? N1 C30 C31 110.4(2) . . ? N1 C30 C23 111.6(2) . . ? C31 C30 C23 109.4(2) . . ? C32 C31 C36 118.9(3) . . ? C32 C31 C30 119.6(2) . . ? C36 C31 C30 121.5(2) . . ? C31 C32 C33 120.5(3) . . ? C34 C33 C32 120.6(3) . . ? C33 C34 C35 119.5(3) . . ? C34 C35 C36 120.0(3) . . ? C31 C36 C35 120.5(3) . . ? O42 C42 C41 106.4(4) . . ? O42 C42 C43 105.4(5) . . ? C41 C42 C43 119.4(6) . . ? C42 C43 C44 111.0(6) . . ? C45 C44 C43 114.1(6) . . ? C44 C45 C46 114.5(6) . . ? O52 C52 C51 114.1(10) . . ? O52 C52 C53 100.1(10) . . ? C51 C52 C53 108.2(11) . . ? C54 C53 C52 111.8(12) . . ? C53 C54 C55 113.8(12) . . ? C54 C55 C56 122.8(12) . . ? _diffrn_measured_fraction_theta_max 0.976 _diffrn_reflns_theta_full 27.90 _diffrn_measured_fraction_theta_full 0.976 _refine_diff_density_max 0.787 _refine_diff_density_min -0.352 _refine_diff_density_rms 0.058 #===END data_imai5_6 _database_code_depnum_ccdc_archive 'CCDC 287393' #data_ima568a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C86 H96 N4 O12' _chemical_formula_weight 1377.67 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 9.5777(6) _cell_length_b 27.1971(17) _cell_length_c 28.9068(17) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 7529.8(8) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9999 _cell_measurement_theta_min 1.65 _cell_measurement_theta_max 27.94 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.215 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2944 _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9685 _exptl_absorpt_correction_T_max 0.9920 _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 'Bruker APEX' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 48549 _diffrn_reflns_av_R_equivalents 0.0745 _diffrn_reflns_av_sigmaI/netI 0.1175 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -35 _diffrn_reflns_limit_k_max 35 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 37 _diffrn_reflns_theta_min 1.65 _diffrn_reflns_theta_max 27.94 _reflns_number_total 17745 _reflns_number_gt 10882 _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 ; Two 2-heptanols of different chirality (from O302 to C307 and from O312 and C317) share the same site. Their occupancies were refined. The positions of the hydrogens attached to O302 and O312 were not assigned. 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^)+(0.0779P)^2^+0.4059P] 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 -1.5(10) _refine_ls_number_reflns 17745 _refine_ls_number_parameters 917 _refine_ls_number_restraints 62 _refine_ls_R_factor_all 0.1249 _refine_ls_R_factor_gt 0.0689 _refine_ls_wR_factor_ref 0.1737 _refine_ls_wR_factor_gt 0.1508 _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_restrained_S_all 1.038 _refine_ls_shift/su_max 0.019 _refine_ls_shift/su_mean 0.008 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 0.0413(3) 0.30192(12) 0.87014(11) 0.0242(7) Uani 1 1 d . . . C2 C -0.0214(3) 0.31510(12) 0.91120(12) 0.0239(7) Uani 1 1 d . . . C3 C -0.0760(3) 0.36275(12) 0.91796(13) 0.0299(8) Uani 1 1 d . . . H3 H -0.1170 0.3710 0.9461 0.036 Uiso 1 1 calc R . . C4 C -0.0687(4) 0.39672(13) 0.88344(14) 0.0370(9) Uani 1 1 d . . . H4 H -0.1040 0.4281 0.8884 0.044 Uiso 1 1 calc R . . C5 C -0.0028(4) 0.41986(15) 0.80392(16) 0.0465(11) Uani 1 1 d . . . H5 H -0.0412 0.4510 0.8080 0.056 Uiso 1 1 calc R . . C6 C 0.0584(4) 0.40824(17) 0.76289(16) 0.0507(12) Uani 1 1 d . . . H6 H 0.0625 0.4316 0.7394 0.061 Uiso 1 1 calc R . . C7 C 0.1154(5) 0.36134(17) 0.75566(14) 0.0498(11) Uani 1 1 d . . . H7 H 0.1570 0.3538 0.7275 0.060 Uiso 1 1 calc R . . C8 C 0.1098(4) 0.32625(15) 0.79035(12) 0.0390(9) Uani 1 1 d . . . H8 H 0.1466 0.2951 0.7852 0.047 Uiso 1 1 calc R . . C9 C 0.0482(4) 0.33758(13) 0.83372(12) 0.0316(8) Uani 1 1 d . . . C10 C -0.0089(4) 0.38512(14) 0.84072(14) 0.0379(9) Uani 1 1 d . . . C11 C 0.0884(3) 0.25084(12) 0.86079(10) 0.0254(7) Uani 1 1 d . . . C12 C 0.2247(3) 0.23469(12) 0.86373(11) 0.0248(7) Uani 1 1 d . . . C13 C 0.2594(4) 0.18584(13) 0.85146(11) 0.0305(8) Uani 1 1 d . . . H13 H 0.3523 0.1760 0.8523 0.037 Uiso 1 1 calc R . . C14 C 0.1606(4) 0.15319(13) 0.83854(12) 0.0347(9) Uani 1 1 d . . . H14 H 0.1868 0.1215 0.8301 0.042 Uiso 1 1 calc R . . C15 C -0.0886(4) 0.13249(15) 0.82640(13) 0.0415(10) Uani 1 1 d . . . H15 H -0.0651 0.1001 0.8195 0.050 Uiso 1 1 calc R . . C16 C -0.2257(5) 0.14636(17) 0.82557(15) 0.0514(12) Uani 1 1 d . . . H16 H -0.2945 0.1236 0.8181 0.062 Uiso 1 1 calc R . . C17 C -0.2620(4) 0.19449(16) 0.83582(13) 0.0418(10) Uani 1 1 d . . . H17 H -0.3556 0.2035 0.8357 0.050 Uiso 1 1 calc R . . C18 C -0.1625(4) 0.22925(14) 0.84621(12) 0.0343(9) Uani 1 1 d . . . H18 H -0.1890 0.2616 0.8521 0.041 Uiso 1 1 calc R . . C19 C -0.0194(3) 0.21587(13) 0.84804(11) 0.0278(8) Uani 1 1 d . . . C20 C 0.0184(4) 0.16650(13) 0.83766(12) 0.0324(8) Uani 1 1 d . . . C21 C -0.0350(3) 0.27831(11) 0.95003(11) 0.0219(7) Uani 1 1 d . . . O22 O 0.0635(2) 0.24860(8) 0.95698(7) 0.0237(5) Uani 1 1 d . . . O23 O -0.1456(2) 0.27984(8) 0.97407(8) 0.0266(5) Uani 1 1 d . . . C24 C 0.3391(4) 0.26709(13) 0.88413(11) 0.0285(8) Uani 1 1 d . . . O25 O 0.3118(2) 0.31140(8) 0.89241(8) 0.0279(5) Uani 1 1 d . . . O26 O 0.4528(3) 0.24669(9) 0.89343(9) 0.0405(7) Uani 1 1 d . . . C31 C 0.9027(3) 0.39405(11) 0.51266(11) 0.0219(7) Uani 1 1 d . . . C32 C 1.0409(3) 0.39292(11) 0.49960(12) 0.0244(7) Uani 1 1 d . . . C33 C 1.0797(4) 0.41018(11) 0.45528(12) 0.0297(8) Uani 1 1 d . . . H33 H 1.1737 0.4106 0.4472 0.036 Uiso 1 1 calc R . . C34 C 0.9834(4) 0.42610(12) 0.42432(12) 0.0296(8) Uani 1 1 d . . . H34 H 1.0121 0.4379 0.3957 0.036 Uiso 1 1 calc R . . C35 C 0.7364(4) 0.43879(13) 0.40253(13) 0.0331(8) Uani 1 1 d . . . H35 H 0.7635 0.4498 0.3734 0.040 Uiso 1 1 calc R . . C36 C 0.5986(4) 0.43626(13) 0.41309(13) 0.0363(9) Uani 1 1 d . . . H36 H 0.5321 0.4456 0.3914 0.044 Uiso 1 1 calc R . . C37 C 0.5562(4) 0.41935(12) 0.45713(13) 0.0318(8) Uani 1 1 d . . . H37 H 0.4616 0.4167 0.4640 0.038 Uiso 1 1 calc R . . C38 C 0.6523(3) 0.40695(11) 0.48950(12) 0.0239(7) Uani 1 1 d . . . H38 H 0.6225 0.3967 0.5186 0.029 Uiso 1 1 calc R . . C39 C 0.7987(3) 0.40927(11) 0.47984(12) 0.0244(7) Uani 1 1 d . . . C40 C 0.8402(4) 0.42489(12) 0.43529(12) 0.0276(8) Uani 1 1 d . . . C41 C 0.8543(3) 0.38062(11) 0.56023(11) 0.0226(7) Uani 1 1 d . . . C42 C 0.7926(3) 0.33583(11) 0.56946(11) 0.0222(7) Uani 1 1 d . . . C43 C 0.7431(3) 0.32408(12) 0.61397(12) 0.0252(7) Uani 1 1 d . . . H43 H 0.7006 0.2938 0.6192 0.030 Uiso 1 1 calc R . . C44 C 0.7574(3) 0.35711(13) 0.64980(12) 0.0286(8) Uani 1 1 d . . . H44 H 0.7291 0.3485 0.6795 0.034 Uiso 1 1 calc R . . C45 C 0.8249(4) 0.43988(14) 0.67730(13) 0.0349(9) Uani 1 1 d . . . H45 H 0.7953 0.4320 0.7070 0.042 Uiso 1 1 calc R . . C46 C 0.8771(4) 0.48507(14) 0.66844(14) 0.0412(10) Uani 1 1 d . . . H46 H 0.8843 0.5079 0.6923 0.049 Uiso 1 1 calc R . . C47 C 0.9205(4) 0.49802(13) 0.62377(14) 0.0384(9) Uani 1 1 d . . . H47 H 0.9538 0.5295 0.6180 0.046 Uiso 1 1 calc R . . C48 C 0.9139(4) 0.46433(12) 0.58857(13) 0.0315(8) Uani 1 1 d . . . H48 H 0.9447 0.4731 0.5592 0.038 Uiso 1 1 calc R . . C49 C 0.8615(3) 0.41683(12) 0.59612(12) 0.0277(8) Uani 1 1 d . . . C50 C 0.8150(3) 0.40420(13) 0.64145(12) 0.0298(8) Uani 1 1 d . . . C51 C 1.1519(3) 0.36907(11) 0.52893(13) 0.0280(8) Uani 1 1 d . . . O52 O 1.1211(2) 0.35458(8) 0.56923(8) 0.0296(5) Uani 1 1 d . . . O53 O 1.2696(2) 0.36249(9) 0.51091(9) 0.0385(6) Uani 1 1 d . . . C54 C 0.7762(3) 0.29809(11) 0.53197(12) 0.0224(7) Uani 1 1 d . . . O55 O 0.8730(2) 0.29356(7) 0.50293(8) 0.0260(5) Uani 1 1 d . . . O56 O 0.6660(2) 0.27215(8) 0.53161(8) 0.0281(5) Uani 1 1 d . . . C61 C 0.1224(3) 0.22489(11) 0.63974(12) 0.0238(7) Uani 1 1 d . . . C62 C 0.1324(4) 0.18095(12) 0.66390(12) 0.0322(8) Uani 1 1 d . . . H62 H 0.1863 0.1554 0.6521 0.039 Uiso 1 1 calc R . . C63 C 0.0631(4) 0.17479(14) 0.70543(13) 0.0394(9) Uani 1 1 d . . . H63 H 0.0719 0.1454 0.7215 0.047 Uiso 1 1 calc R . . C64 C -0.0184(4) 0.21172(14) 0.72306(12) 0.0352(9) Uani 1 1 d . . . H64 H -0.0663 0.2071 0.7507 0.042 Uiso 1 1 calc R . . C65 C -0.0293(4) 0.25570(14) 0.69976(12) 0.0349(9) Uani 1 1 d . . . H65 H -0.0842 0.2809 0.7118 0.042 Uiso 1 1 calc R . . C66 C 0.0414(3) 0.26248(12) 0.65849(12) 0.0288(8) Uani 1 1 d . . . H66 H 0.0349 0.2924 0.6431 0.035 Uiso 1 1 calc R . . C67 C 0.1981(3) 0.23198(12) 0.59514(11) 0.0225(7) Uani 1 1 d . . . H67 H 0.2330 0.1999 0.5848 0.027 Uiso 1 1 calc R . . N68 N 0.0989(3) 0.25133(10) 0.55909(9) 0.0242(6) Uani 1 1 d . . . H68A H 0.1444 0.2556 0.5325 0.036 Uiso 1 1 calc R . . H68B H 0.0639 0.2800 0.5685 0.036 Uiso 1 1 calc R . . H68C H 0.0298 0.2299 0.5550 0.036 Uiso 1 1 calc R . . C69 C 0.4296(3) 0.24262(12) 0.63342(12) 0.0257(7) Uani 1 1 d . . . C70 C 0.4492(4) 0.25974(15) 0.67759(13) 0.0378(9) Uani 1 1 d . . . H70 H 0.3999 0.2872 0.6875 0.045 Uiso 1 1 calc R . . C71 C 0.5417(4) 0.23673(16) 0.70780(14) 0.0468(11) Uani 1 1 d . . . H71 H 0.5534 0.2483 0.7378 0.056 Uiso 1 1 calc R . . C72 C 0.6166(4) 0.19592(16) 0.69226(15) 0.0468(11) Uani 1 1 d . . . H72 H 0.6787 0.1801 0.7120 0.056 Uiso 1 1 calc R . . C73 C 0.5989(4) 0.17907(14) 0.64801(14) 0.0362(9) Uani 1 1 d . . . H73 H 0.6505 0.1523 0.6377 0.043 Uiso 1 1 calc R . . C74 C 0.5056(3) 0.20146(13) 0.61874(13) 0.0314(8) Uani 1 1 d . . . H74 H 0.4927 0.1892 0.5890 0.038 Uiso 1 1 calc R . . C75 C 0.3247(3) 0.26669(12) 0.60231(11) 0.0243(7) Uani 1 1 d . . . H75 H 0.2914 0.2967 0.6175 0.029 Uiso 1 1 calc R . . N76 N 0.3868(3) 0.28084(9) 0.55666(9) 0.0233(6) Uani 1 1 d . . . H76A H 0.3217 0.2950 0.5392 0.035 Uiso 1 1 calc R . . H76B H 0.4190 0.2541 0.5425 0.035 Uiso 1 1 calc R . . H76C H 0.4567 0.3019 0.5612 0.035 Uiso 1 1 calc R . . C81 C 0.8748(3) 0.61378(11) 0.49597(12) 0.0235(7) Uani 1 1 d . . . C82 C 0.8397(3) 0.56987(12) 0.47442(12) 0.0278(8) Uani 1 1 d . . . H82 H 0.8843 0.5608 0.4472 0.033 Uiso 1 1 calc R . . C83 C 0.7382(3) 0.53951(12) 0.49343(13) 0.0322(8) Uani 1 1 d . . . H83 H 0.7142 0.5103 0.4786 0.039 Uiso 1 1 calc R . . C84 C 0.6731(3) 0.55239(12) 0.53395(14) 0.0342(9) Uani 1 1 d . . . H84 H 0.6052 0.5319 0.5465 0.041 Uiso 1 1 calc R . . C85 C 0.7080(3) 0.59558(13) 0.55609(13) 0.0309(8) Uani 1 1 d . . . H85 H 0.6643 0.6039 0.5837 0.037 Uiso 1 1 calc R . . C86 C 0.8083(3) 0.62665(12) 0.53732(12) 0.0252(7) Uani 1 1 d . . . H86 H 0.8312 0.6559 0.5522 0.030 Uiso 1 1 calc R . . C87 C 0.9843(3) 0.64681(11) 0.47469(11) 0.0214(7) Uani 1 1 d . . . H87 H 1.0134 0.6323 0.4452 0.026 Uiso 1 1 calc R . . N88 N 0.9245(2) 0.69638(9) 0.46519(9) 0.0203(6) Uani 1 1 d . . . H88A H 0.9896 0.7154 0.4525 0.030 Uiso 1 1 calc R . . H88B H 0.8954 0.7098 0.4916 0.030 Uiso 1 1 calc R . . H88C H 0.8527 0.6935 0.4458 0.030 Uiso 1 1 calc R . . C89 C 1.1854(3) 0.60141(11) 0.50829(12) 0.0230(7) Uani 1 1 d . . . C90 C 1.1754(4) 0.57311(13) 0.54738(13) 0.0354(9) Uani 1 1 d . . . H90 H 1.1277 0.5851 0.5731 0.043 Uiso 1 1 calc R . . C91 C 1.2358(4) 0.52678(14) 0.54896(16) 0.0465(11) Uani 1 1 d . . . H91 H 1.2280 0.5079 0.5756 0.056 Uiso 1 1 calc R . . C92 C 1.3066(4) 0.50875(14) 0.51159(16) 0.0445(10) Uani 1 1 d . . . H92 H 1.3452 0.4774 0.5126 0.053 Uiso 1 1 calc R . . C93 C 1.3206(4) 0.53711(14) 0.47267(16) 0.0457(10) Uani 1 1 d . . . H93 H 1.3725 0.5256 0.4477 0.055 Uiso 1 1 calc R . . C94 C 1.2574(4) 0.58299(13) 0.47045(13) 0.0343(9) Uani 1 1 d . . . H94 H 1.2634 0.6015 0.4434 0.041 Uiso 1 1 calc R . . C95 C 1.1133(3) 0.65037(11) 0.50619(11) 0.0213(7) Uani 1 1 d . . . H95 H 1.0822 0.6590 0.5374 0.026 Uiso 1 1 calc R . . N96 N 1.2115(3) 0.68896(9) 0.48979(10) 0.0234(6) Uani 1 1 d . . . H96A H 1.1676 0.7178 0.4888 0.035 Uiso 1 1 calc R . . H96B H 1.2419 0.6813 0.4616 0.035 Uiso 1 1 calc R . . H96C H 1.2836 0.6909 0.5091 0.035 Uiso 1 1 calc R . . O101 O 0.8607(2) 0.19004(9) 0.56554(9) 0.0366(6) Uani 1 1 d D . . O102 O 0.4426(2) 0.67494(9) 0.54848(9) 0.0369(6) Uani 1 1 d D . . O202 O 0.2814(7) 0.3778(2) 0.6509(2) 0.061(2) Uiso 0.648(8) 1 d PD A 1 C201 C 0.4427(11) 0.4131(4) 0.6027(3) 0.084(4) Uiso 0.648(8) 1 d PD A 1 H20A H 0.3994 0.4020 0.5746 0.126 Uiso 0.648(8) 1 calc PR A 1 H20B H 0.4992 0.3872 0.6153 0.126 Uiso 0.648(8) 1 calc PR A 1 H20C H 0.5003 0.4412 0.5962 0.126 Uiso 0.648(8) 1 calc PR A 1 C202 C 0.3280(6) 0.42762(18) 0.63827(17) 0.0314(15) Uiso 0.648(8) 1 d PD A 1 H202 H 0.2547 0.4493 0.6262 0.038 Uiso 0.648(8) 1 calc PR A 1 C203 C 0.3993(7) 0.4456(2) 0.6823(2) 0.0455(19) Uiso 0.648(8) 1 d PD A 1 H20D H 0.4740 0.4230 0.6903 0.055 Uiso 0.648(8) 1 calc PR A 1 H20E H 0.3321 0.4452 0.7075 0.055 Uiso 0.648(8) 1 calc PR A 1 C204 C 0.4600(8) 0.4978(2) 0.6777(2) 0.053(2) Uiso 0.648(8) 1 d PD A 1 H20F H 0.5287 0.4981 0.6530 0.063 Uiso 0.648(8) 1 calc PR A 1 H20G H 0.3857 0.5203 0.6692 0.063 Uiso 0.648(8) 1 calc PR A 1 C205 C 0.5279(11) 0.5156(3) 0.7220(3) 0.075(3) Uiso 0.648(8) 1 d PD A 1 H20H H 0.6167 0.4989 0.7258 0.090 Uiso 0.648(8) 1 calc PR A 1 H20I H 0.4690 0.5067 0.7479 0.090 Uiso 0.648(8) 1 calc PR A 1 C206 C 0.5528(9) 0.5716(2) 0.7228(3) 0.059(2) Uiso 0.648(8) 1 d PD A 1 H20J H 0.5961 0.5814 0.6939 0.071 Uiso 0.648(8) 1 calc PR A 1 H20K H 0.4632 0.5882 0.7249 0.071 Uiso 0.648(8) 1 calc PR A 1 C207 C 0.6449(11) 0.5888(4) 0.7629(4) 0.101(4) Uiso 0.648(8) 1 d PD A 1 H20L H 0.6559 0.6239 0.7615 0.151 Uiso 0.648(8) 1 calc PR A 1 H20M H 0.7348 0.5734 0.7608 0.151 Uiso 0.648(8) 1 calc PR A 1 H20N H 0.6018 0.5800 0.7918 0.151 Uiso 0.648(8) 1 calc PR A 1 O212 O 0.2415(9) 0.3856(3) 0.6483(3) 0.029(2) Uiso 0.352(8) 1 d PD A 2 C211 C 0.4368(12) 0.4262(5) 0.6016(4) 0.026(3) Uiso 0.352(8) 1 d PD A 2 H21A H 0.4843 0.3976 0.5901 0.038 Uiso 0.352(8) 1 calc PR A 2 H21B H 0.4993 0.4538 0.6013 0.038 Uiso 0.352(8) 1 calc PR A 2 H21C H 0.3576 0.4332 0.5823 0.038 Uiso 0.352(8) 1 calc PR A 2 C212 C 0.3883(14) 0.4168(4) 0.6504(4) 0.060(4) Uiso 0.352(8) 1 d PD A 2 H212 H 0.4595 0.4025 0.6707 0.072 Uiso 0.352(8) 1 calc PR A 2 C213 C 0.3113(14) 0.4595(4) 0.6709(5) 0.054(4) Uiso 0.352(8) 1 d PD A 2 H21D H 0.2840 0.4499 0.7019 0.065 Uiso 0.352(8) 1 calc PR A 2 H21E H 0.2259 0.4633 0.6532 0.065 Uiso 0.352(8) 1 calc PR A 2 C214 C 0.3781(19) 0.5104(5) 0.6745(6) 0.084(5) Uiso 0.352(8) 1 d PD A 2 H21F H 0.4141 0.5179 0.6439 0.101 Uiso 0.352(8) 1 calc PR A 2 H21G H 0.3019 0.5332 0.6799 0.101 Uiso 0.352(8) 1 calc PR A 2 C215 C 0.4852(17) 0.5241(5) 0.7061(6) 0.068(5) Uiso 0.352(8) 1 d PD A 2 H21H H 0.5502 0.4967 0.7068 0.082 Uiso 0.352(8) 1 calc PR A 2 H21I H 0.4416 0.5253 0.7363 0.082 Uiso 0.352(8) 1 calc PR A 2 C216 C 0.575(2) 0.5710(6) 0.7021(7) 0.088(6) Uiso 0.352(8) 1 d PD A 2 H21J H 0.5185 0.6006 0.7008 0.105 Uiso 0.352(8) 1 calc PR A 2 H21K H 0.6379 0.5699 0.6759 0.105 Uiso 0.352(8) 1 calc PR A 2 C217 C 0.659(2) 0.5655(9) 0.7525(7) 0.106(7) Uiso 0.352(8) 1 d PD A 2 H21L H 0.7195 0.5933 0.7568 0.159 Uiso 0.352(8) 1 calc PR A 2 H21M H 0.7138 0.5359 0.7523 0.159 Uiso 0.352(8) 1 calc PR A 2 H21N H 0.5926 0.5641 0.7773 0.159 Uiso 0.352(8) 1 calc PR A 2 O302 O 0.5505(5) 0.36677(17) 0.86800(15) 0.0455(13) Uiso 0.687(6) 1 d PD B 1 C301 C 0.5427(10) 0.3519(3) 0.7874(3) 0.070(2) Uiso 0.687(6) 1 d PD B 1 H30A H 0.6286 0.3338 0.7899 0.105 Uiso 0.687(6) 1 calc PR B 1 H30B H 0.5366 0.3666 0.7573 0.105 Uiso 0.687(6) 1 calc PR B 1 H30C H 0.4654 0.3299 0.7919 0.105 Uiso 0.687(6) 1 calc PR B 1 C302 C 0.5390(9) 0.3926(3) 0.8248(2) 0.062(3) Uiso 0.687(6) 1 d PD B 1 H302 H 0.6198 0.4143 0.8210 0.075 Uiso 0.687(6) 1 calc PR B 1 C303 C 0.4059(6) 0.4225(2) 0.8222(2) 0.0547(19) Uiso 0.687(6) 1 d PD B 1 H30D H 0.3960 0.4351 0.7910 0.066 Uiso 0.687(6) 1 calc PR B 1 H30E H 0.3273 0.4009 0.8281 0.066 Uiso 0.687(6) 1 calc PR B 1 C304 C 0.3996(7) 0.4645(2) 0.8551(2) 0.0577(19) Uiso 0.687(6) 1 d PD B 1 H30F H 0.4814 0.4848 0.8501 0.069 Uiso 0.687(6) 1 calc PR B 1 H30G H 0.4057 0.4514 0.8862 0.069 Uiso 0.687(6) 1 calc PR B 1 C305 C 0.2715(7) 0.4973(2) 0.8525(2) 0.0495(18) Uiso 0.687(6) 1 d PD B 1 H30H H 0.1886 0.4768 0.8527 0.059 Uiso 0.687(6) 1 calc PR B 1 H30I H 0.2687 0.5180 0.8798 0.059 Uiso 0.687(6) 1 calc PR B 1 C306 C 0.2678(7) 0.5298(3) 0.8099(2) 0.063(2) Uiso 0.687(6) 1 d PD B 1 H30J H 0.3465 0.5522 0.8116 0.076 Uiso 0.687(6) 1 calc PR B 1 H30K H 0.2824 0.5090 0.7830 0.076 Uiso 0.687(6) 1 calc PR B 1 C307 C 0.1381(9) 0.5601(3) 0.8014(3) 0.075(2) Uiso 0.687(6) 1 d PD B 1 H30L H 0.1499 0.5792 0.7738 0.113 Uiso 0.687(6) 1 calc PR B 1 H30M H 0.1226 0.5816 0.8272 0.113 Uiso 0.687(6) 1 calc PR B 1 H30N H 0.0592 0.5386 0.7978 0.113 Uiso 0.687(6) 1 calc PR B 1 O312 O 0.5005(16) 0.3774(5) 0.8677(5) 0.086(5) Uiso 0.313(6) 1 d PD B 2 C311 C 0.610(3) 0.3449(7) 0.7984(8) 0.102(7) Uiso 0.313(6) 1 d PD B 2 H31A H 0.5670 0.3131 0.8006 0.152 Uiso 0.313(6) 1 calc PR B 2 H31B H 0.6951 0.3451 0.8158 0.152 Uiso 0.313(6) 1 calc PR B 2 H31C H 0.6294 0.3522 0.7666 0.152 Uiso 0.313(6) 1 calc PR B 2 C312 C 0.505(2) 0.3858(5) 0.8189(5) 0.054(6) Uiso 0.313(6) 1 d PD B 2 H312 H 0.4124 0.3843 0.8047 0.065 Uiso 0.313(6) 1 calc PR B 2 C313 C 0.5748(18) 0.4346(5) 0.8112(6) 0.081(6) Uiso 0.313(6) 1 d PD B 2 H31D H 0.5888 0.4398 0.7784 0.097 Uiso 0.313(6) 1 calc PR B 2 H31E H 0.6657 0.4346 0.8261 0.097 Uiso 0.313(6) 1 calc PR B 2 C314 C 0.4868(16) 0.4760(6) 0.8307(7) 0.090(6) Uiso 0.313(6) 1 d PD B 2 H31F H 0.4982 0.4752 0.8641 0.108 Uiso 0.313(6) 1 calc PR B 2 H31G H 0.5282 0.5065 0.8201 0.108 Uiso 0.313(6) 1 calc PR B 2 C315 C 0.3377(14) 0.4793(5) 0.8217(6) 0.065(5) Uiso 0.313(6) 1 d PD B 2 H31H H 0.2988 0.4471 0.8281 0.078 Uiso 0.313(6) 1 calc PR B 2 H31I H 0.3273 0.4846 0.7887 0.078 Uiso 0.313(6) 1 calc PR B 2 C316 C 0.2442(19) 0.5165(6) 0.8455(6) 0.071(5) Uiso 0.313(6) 1 d PD B 2 H31J H 0.1583 0.4999 0.8541 0.086 Uiso 0.313(6) 1 calc PR B 2 H31K H 0.2897 0.5265 0.8740 0.086 Uiso 0.313(6) 1 calc PR B 2 C317 C 0.207(2) 0.5609(6) 0.8199(7) 0.081(6) Uiso 0.313(6) 1 d PD B 2 H31L H 0.1503 0.5817 0.8390 0.121 Uiso 0.313(6) 1 calc PR B 2 H31M H 0.1558 0.5521 0.7926 0.121 Uiso 0.313(6) 1 calc PR B 2 H31N H 0.2904 0.5782 0.8112 0.121 Uiso 0.313(6) 1 calc PR B 2 H01B H 0.782(3) 0.2109(12) 0.5750(11) 0.050 Uiso 1 1 d D . . H01A H 0.842(4) 0.1726(12) 0.5362(8) 0.050 Uiso 1 1 d D . . H02B H 0.470(3) 0.6983(11) 0.5731(9) 0.050 Uiso 1 1 d D . . H02A H 0.528(2) 0.6589(12) 0.5360(12) 0.050 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 0.0185(15) 0.0309(18) 0.0231(18) 0.0020(14) -0.0043(14) -0.0011(13) C2 0.0130(15) 0.0257(18) 0.033(2) 0.0059(15) -0.0021(14) -0.0011(13) C3 0.0211(18) 0.0282(19) 0.040(2) 0.0021(16) 0.0029(16) 0.0026(14) C4 0.0256(19) 0.030(2) 0.056(3) 0.0084(18) -0.0031(18) 0.0020(15) C5 0.035(2) 0.046(2) 0.058(3) 0.029(2) -0.015(2) -0.0079(18) C6 0.041(2) 0.061(3) 0.050(3) 0.033(2) -0.013(2) -0.020(2) C7 0.050(3) 0.067(3) 0.033(2) 0.016(2) -0.002(2) -0.023(2) C8 0.042(2) 0.049(2) 0.026(2) 0.0071(17) -0.0084(17) -0.0132(19) C9 0.0215(17) 0.040(2) 0.034(2) 0.0116(16) -0.0080(16) -0.0090(15) C10 0.026(2) 0.039(2) 0.049(3) 0.0126(19) -0.0091(18) -0.0075(16) C11 0.0312(18) 0.0314(18) 0.0137(16) 0.0016(14) 0.0005(14) -0.0037(15) C12 0.0232(17) 0.0309(19) 0.0205(18) -0.0004(14) 0.0001(14) -0.0010(14) C13 0.0278(18) 0.042(2) 0.0216(18) -0.0008(16) -0.0006(15) 0.0071(16) C14 0.046(2) 0.0301(19) 0.028(2) -0.0042(16) -0.0020(18) -0.0003(17) C15 0.044(2) 0.045(2) 0.036(2) -0.0049(18) -0.0009(19) -0.0132(19) C16 0.053(3) 0.054(3) 0.047(3) -0.004(2) -0.004(2) -0.030(2) C17 0.027(2) 0.056(3) 0.043(2) 0.000(2) -0.0012(18) -0.0142(18) C18 0.0294(19) 0.047(2) 0.0260(19) 0.0002(16) 0.0012(16) -0.0109(17) C19 0.0265(18) 0.038(2) 0.0188(18) 0.0022(15) -0.0002(14) -0.0061(15) C20 0.039(2) 0.035(2) 0.0225(19) 0.0027(15) -0.0027(16) -0.0088(17) C21 0.0195(16) 0.0217(16) 0.0244(18) -0.0037(14) -0.0008(14) -0.0055(13) O22 0.0209(11) 0.0250(12) 0.0251(12) 0.0015(9) 0.0027(10) 0.0037(10) O23 0.0178(11) 0.0298(12) 0.0324(13) 0.0047(10) 0.0038(10) 0.0020(9) C24 0.0258(18) 0.040(2) 0.0201(18) 0.0023(15) 0.0000(15) -0.0002(16) O25 0.0249(12) 0.0287(13) 0.0301(13) -0.0023(10) -0.0003(10) 0.0009(10) O26 0.0281(13) 0.0411(15) 0.0522(17) -0.0085(13) -0.0152(12) 0.0102(12) C31 0.0215(16) 0.0134(15) 0.0308(19) -0.0004(13) 0.0003(14) 0.0002(12) C32 0.0184(15) 0.0183(16) 0.036(2) 0.0023(14) 0.0025(15) 0.0003(13) C33 0.0234(17) 0.0244(18) 0.041(2) 0.0025(15) 0.0033(16) 0.0017(14) C34 0.0290(19) 0.0286(18) 0.031(2) 0.0065(15) 0.0065(16) 0.0054(15) C35 0.035(2) 0.034(2) 0.030(2) 0.0039(16) -0.0008(17) 0.0036(16) C36 0.032(2) 0.034(2) 0.043(2) 0.0004(17) -0.0149(18) 0.0044(16) C37 0.0217(17) 0.0273(19) 0.047(2) -0.0035(16) -0.0017(17) 0.0011(14) C38 0.0231(16) 0.0170(16) 0.0317(19) 0.0010(14) 0.0024(15) -0.0001(13) C39 0.0196(16) 0.0215(17) 0.032(2) -0.0018(14) 0.0014(14) 0.0039(13) C40 0.0254(17) 0.0227(17) 0.035(2) 0.0006(15) 0.0019(16) 0.0009(14) C41 0.0127(15) 0.0246(17) 0.0304(19) 0.0021(14) -0.0013(14) 0.0050(12) C42 0.0129(15) 0.0241(17) 0.0297(19) 0.0015(14) 0.0007(14) 0.0042(13) C43 0.0159(16) 0.0254(18) 0.034(2) 0.0051(15) 0.0009(15) 0.0023(13) C44 0.0243(18) 0.036(2) 0.0258(19) 0.0045(16) -0.0006(15) 0.0045(15) C45 0.032(2) 0.041(2) 0.031(2) -0.0031(17) -0.0036(17) 0.0059(17) C46 0.044(2) 0.038(2) 0.042(2) -0.0154(18) -0.0089(19) 0.0024(19) C47 0.040(2) 0.030(2) 0.045(2) -0.0058(17) 0.0001(19) 0.0000(16) C48 0.0307(19) 0.0275(19) 0.036(2) 0.0003(16) -0.0033(17) 0.0028(15) C49 0.0182(16) 0.0323(19) 0.033(2) 0.0037(15) -0.0010(15) 0.0035(14) C50 0.0197(17) 0.038(2) 0.032(2) 0.0009(16) -0.0019(15) 0.0070(15) C51 0.0226(17) 0.0226(17) 0.039(2) 0.0023(15) 0.0039(16) 0.0007(14) O52 0.0243(12) 0.0322(13) 0.0322(14) 0.0062(10) 0.0027(11) 0.0036(10) O53 0.0219(13) 0.0460(15) 0.0477(16) 0.0151(12) 0.0074(12) 0.0095(11) C54 0.0193(16) 0.0204(16) 0.0273(18) 0.0068(14) -0.0036(15) 0.0014(13) O55 0.0188(11) 0.0259(12) 0.0333(14) 0.0011(10) 0.0073(10) -0.0009(9) O56 0.0178(11) 0.0312(12) 0.0352(14) 0.0012(10) 0.0017(10) -0.0040(9) C61 0.0145(15) 0.0250(17) 0.0318(19) -0.0018(14) -0.0034(14) -0.0002(13) C62 0.035(2) 0.0282(19) 0.034(2) 0.0027(16) 0.0011(16) 0.0044(15) C63 0.042(2) 0.041(2) 0.035(2) 0.0143(17) -0.0004(19) -0.0032(18) C64 0.0299(19) 0.056(2) 0.0199(19) 0.0044(17) -0.0012(15) -0.0009(18) C65 0.0278(19) 0.048(2) 0.028(2) -0.0063(17) -0.0026(16) 0.0076(17) C66 0.0259(18) 0.0299(19) 0.031(2) 0.0007(15) 0.0004(16) 0.0003(14) C67 0.0156(15) 0.0240(17) 0.0278(18) 0.0019(14) -0.0045(14) 0.0028(13) N68 0.0166(13) 0.0320(15) 0.0240(14) 0.0021(12) -0.0008(11) 0.0010(11) C69 0.0146(15) 0.0298(18) 0.033(2) 0.0009(15) 0.0003(14) -0.0028(13) C70 0.0292(19) 0.046(2) 0.038(2) -0.0013(18) -0.0070(17) -0.0006(17) C71 0.045(2) 0.061(3) 0.034(2) -0.002(2) -0.019(2) -0.003(2) C72 0.024(2) 0.058(3) 0.058(3) 0.015(2) -0.0164(19) 0.0004(19) C73 0.0213(18) 0.040(2) 0.047(2) 0.0080(18) -0.0042(17) 0.0039(16) C74 0.0213(17) 0.037(2) 0.036(2) 0.0034(17) 0.0014(16) -0.0010(15) C75 0.0162(16) 0.0256(17) 0.0312(19) 0.0019(14) -0.0010(14) 0.0011(13) N76 0.0140(12) 0.0251(14) 0.0309(16) 0.0029(12) 0.0007(12) -0.0006(11) C81 0.0156(15) 0.0226(16) 0.0323(19) 0.0013(14) -0.0052(14) 0.0044(13) C82 0.0208(16) 0.0268(17) 0.036(2) -0.0059(15) -0.0048(15) 0.0015(14) C83 0.0295(18) 0.0152(16) 0.052(2) -0.0002(16) -0.0069(18) -0.0014(14) C84 0.0227(17) 0.0288(19) 0.051(2) 0.0100(17) -0.0014(18) -0.0077(15) C85 0.0258(18) 0.033(2) 0.034(2) 0.0074(16) 0.0008(16) -0.0004(15) C86 0.0193(16) 0.0251(17) 0.031(2) -0.0004(14) 0.0018(15) -0.0028(13) C87 0.0155(15) 0.0197(16) 0.0290(19) -0.0021(14) 0.0004(14) 0.0038(12) N88 0.0129(12) 0.0234(14) 0.0245(14) -0.0026(11) -0.0022(11) -0.0006(10) C89 0.0140(15) 0.0212(16) 0.034(2) 0.0017(14) -0.0040(14) -0.0028(12) C90 0.0299(19) 0.0322(19) 0.044(2) 0.0063(17) 0.0031(18) 0.0044(16) C91 0.045(2) 0.038(2) 0.057(3) 0.019(2) -0.009(2) 0.0056(19) C92 0.036(2) 0.030(2) 0.068(3) 0.005(2) -0.007(2) 0.0114(17) C93 0.036(2) 0.036(2) 0.065(3) -0.009(2) 0.001(2) 0.0109(18) C94 0.0300(19) 0.033(2) 0.040(2) 0.0007(17) 0.0000(18) 0.0055(15) C95 0.0165(15) 0.0250(17) 0.0226(17) 0.0012(13) 0.0030(14) -0.0002(13) N96 0.0157(13) 0.0230(14) 0.0315(16) -0.0013(12) -0.0025(12) 0.0014(11) O101 0.0255(13) 0.0317(14) 0.0525(17) 0.0025(12) 0.0021(12) -0.0021(11) O102 0.0304(13) 0.0428(15) 0.0374(16) 0.0009(12) -0.0058(12) 0.0066(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.378(5) . ? C1 C9 1.433(5) . ? C1 C11 1.486(5) . ? C2 C3 1.411(4) . ? C2 C21 1.509(5) . ? C3 C4 1.361(5) . ? C4 C10 1.397(5) . ? C5 C6 1.360(6) . ? C5 C10 1.424(5) . ? C6 C7 1.403(6) . ? C7 C8 1.385(5) . ? C8 C9 1.419(5) . ? C9 C10 1.418(5) . ? C11 C12 1.380(5) . ? C11 C19 1.451(5) . ? C12 C13 1.415(5) . ? C12 C24 1.525(5) . ? C13 C14 1.350(5) . ? C14 C20 1.409(5) . ? C15 C16 1.366(6) . ? C15 C20 1.419(5) . ? C16 C17 1.386(6) . ? C17 C18 1.376(5) . ? C18 C19 1.419(5) . ? C19 C20 1.423(5) . ? C21 O22 1.259(4) . ? C21 O23 1.267(4) . ? C24 O26 1.252(4) . ? C24 O25 1.256(4) . ? C31 C32 1.377(4) . ? C31 C39 1.436(4) . ? C31 C41 1.497(4) . ? C32 C33 1.414(5) . ? C32 C51 1.506(5) . ? C33 C34 1.356(5) . ? C34 C40 1.409(5) . ? C35 C36 1.356(5) . ? C35 C40 1.424(5) . ? C36 C37 1.413(5) . ? C37 C38 1.355(5) . ? C38 C39 1.431(4) . ? C39 C40 1.413(5) . ? C41 C42 1.380(4) . ? C41 C49 1.432(5) . ? C42 C43 1.408(5) . ? C42 C54 1.501(5) . ? C43 C44 1.378(5) . ? C44 C50 1.415(5) . ? C45 C46 1.351(5) . ? C45 C50 1.423(5) . ? C46 C47 1.401(6) . ? C47 C48 1.371(5) . ? C48 C49 1.403(5) . ? C49 C50 1.426(5) . ? C51 O53 1.255(4) . ? C51 O52 1.265(4) . ? C54 O55 1.257(4) . ? C54 O56 1.269(4) . ? C61 C62 1.388(5) . ? C61 C66 1.393(4) . ? C61 C67 1.492(5) . ? C62 C63 1.382(5) . ? C63 C64 1.371(5) . ? C64 C65 1.377(5) . ? C65 C66 1.384(5) . ? C67 N68 1.505(4) . ? C67 C75 1.551(4) . ? C69 C70 1.372(5) . ? C69 C74 1.401(5) . ? C69 C75 1.499(4) . ? C70 C71 1.393(5) . ? C71 C72 1.395(6) . ? C72 C73 1.369(6) . ? C73 C74 1.373(5) . ? C75 N76 1.498(4) . ? C81 C82 1.388(4) . ? C81 C86 1.399(5) . ? C81 C87 1.512(4) . ? C82 C83 1.389(5) . ? C83 C84 1.372(5) . ? C84 C85 1.379(5) . ? C85 C86 1.390(5) . ? C87 N88 1.490(4) . ? C87 C95 1.538(4) . ? C89 C90 1.371(5) . ? C89 C94 1.387(5) . ? C89 C95 1.501(4) . ? C90 C91 1.387(5) . ? C91 C92 1.367(6) . ? C92 C93 1.371(6) . ? C93 C94 1.388(5) . ? C95 N96 1.487(4) . ? O202 C202 1.472(6) . ? C201 C202 1.555(7) . ? C202 C203 1.526(6) . ? C203 C204 1.541(6) . ? C204 C205 1.516(7) . ? C205 C206 1.543(7) . ? C206 C207 1.530(7) . ? O212 C212 1.643(13) . ? C211 C212 1.506(13) . ? C212 C213 1.497(13) . ? C213 C214 1.530(14) . ? C214 C215 1.421(15) . ? C215 C216 1.544(15) . ? C216 C217 1.671(16) . ? O302 C302 1.436(6) . ? C301 C302 1.548(7) . ? C302 C303 1.515(7) . ? C303 C304 1.486(6) . ? C304 C305 1.520(7) . ? C305 C306 1.517(7) . ? C306 C307 1.510(7) . ? O312 C312 1.429(14) . ? C311 C312 1.610(16) . ? C312 C313 1.502(16) . ? C313 C314 1.515(15) . ? C314 C315 1.455(16) . ? C315 C316 1.517(15) . ? C316 C317 1.462(17) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C9 118.5(3) . . ? C2 C1 C11 122.2(3) . . ? C9 C1 C11 119.0(3) . . ? C1 C2 C3 121.3(3) . . ? C1 C2 C21 120.4(3) . . ? C3 C2 C21 118.3(3) . . ? C4 C3 C2 120.2(3) . . ? C3 C4 C10 121.0(3) . . ? C6 C5 C10 121.0(4) . . ? C5 C6 C7 120.6(4) . . ? C8 C7 C6 120.2(4) . . ? C7 C8 C9 120.4(4) . . ? C10 C9 C8 118.9(3) . . ? C10 C9 C1 119.6(3) . . ? C8 C9 C1 121.4(3) . . ? C4 C10 C9 119.3(3) . . ? C4 C10 C5 121.8(4) . . ? C9 C10 C5 118.8(4) . . ? C12 C11 C19 118.7(3) . . ? C12 C11 C1 125.0(3) . . ? C19 C11 C1 116.3(3) . . ? C11 C12 C13 120.3(3) . . ? C11 C12 C24 121.3(3) . . ? C13 C12 C24 118.1(3) . . ? C14 C13 C12 121.5(3) . . ? C13 C14 C20 120.9(3) . . ? C16 C15 C20 121.2(4) . . ? C15 C16 C17 119.9(4) . . ? C18 C17 C16 121.5(4) . . ? C17 C18 C19 120.1(4) . . ? C18 C19 C20 118.7(3) . . ? C18 C19 C11 121.9(3) . . ? C20 C19 C11 119.4(3) . . ? C14 C20 C15 122.3(3) . . ? C14 C20 C19 119.0(3) . . ? C15 C20 C19 118.7(3) . . ? O22 C21 O23 124.1(3) . . ? O22 C21 C2 118.7(3) . . ? O23 C21 C2 117.3(3) . . ? O26 C24 O25 124.5(3) . . ? O26 C24 C12 116.9(3) . . ? O25 C24 C12 118.6(3) . . ? C32 C31 C39 119.5(3) . . ? C32 C31 C41 123.0(3) . . ? C39 C31 C41 117.6(3) . . ? C31 C32 C33 119.6(3) . . ? C31 C32 C51 122.3(3) . . ? C33 C32 C51 117.9(3) . . ? C34 C33 C32 121.7(3) . . ? C33 C34 C40 120.4(3) . . ? C36 C35 C40 121.1(3) . . ? C35 C36 C37 119.9(3) . . ? C38 C37 C36 120.5(3) . . ? C37 C38 C39 121.3(3) . . ? C40 C39 C38 117.8(3) . . ? C40 C39 C31 119.6(3) . . ? C38 C39 C31 122.5(3) . . ? C34 C40 C39 119.1(3) . . ? C34 C40 C35 121.6(3) . . ? C39 C40 C35 119.3(3) . . ? C42 C41 C49 119.2(3) . . ? C42 C41 C31 121.7(3) . . ? C49 C41 C31 118.9(3) . . ? C41 C42 C43 121.4(3) . . ? C41 C42 C54 120.6(3) . . ? C43 C42 C54 118.0(3) . . ? C44 C43 C42 120.4(3) . . ? C43 C44 C50 120.0(3) . . ? C46 C45 C50 120.5(4) . . ? C45 C46 C47 120.9(3) . . ? C48 C47 C46 120.2(3) . . ? C47 C48 C49 121.1(4) . . ? C48 C49 C50 118.4(3) . . ? C48 C49 C41 122.5(3) . . ? C50 C49 C41 119.0(3) . . ? C44 C50 C45 121.3(3) . . ? C44 C50 C49 119.8(3) . . ? C45 C50 C49 119.0(3) . . ? O53 C51 O52 123.2(3) . . ? O53 C51 C32 117.5(3) . . ? O52 C51 C32 119.2(3) . . ? O55 C54 O56 123.6(3) . . ? O55 C54 C42 118.2(3) . . ? O56 C54 C42 118.2(3) . . ? C62 C61 C66 118.3(3) . . ? C62 C61 C67 120.9(3) . . ? C66 C61 C67 120.8(3) . . ? C63 C62 C61 120.6(3) . . ? C64 C63 C62 120.5(3) . . ? C63 C64 C65 119.9(3) . . ? C64 C65 C66 120.0(3) . . ? C65 C66 C61 120.7(3) . . ? C61 C67 N68 109.7(2) . . ? C61 C67 C75 110.1(3) . . ? N68 C67 C75 111.9(2) . . ? C70 C69 C74 118.8(3) . . ? C70 C69 C75 120.1(3) . . ? C74 C69 C75 121.0(3) . . ? C69 C70 C71 121.2(4) . . ? C70 C71 C72 118.8(4) . . ? C73 C72 C71 120.2(4) . . ? C72 C73 C74 120.5(4) . . ? C73 C74 C69 120.4(4) . . ? N76 C75 C69 112.0(2) . . ? N76 C75 C67 110.5(2) . . ? C69 C75 C67 109.8(2) . . ? C82 C81 C86 119.2(3) . . ? C82 C81 C87 119.8(3) . . ? C86 C81 C87 121.0(3) . . ? C81 C82 C83 120.2(3) . . ? C84 C83 C82 120.2(3) . . ? C83 C84 C85 120.3(3) . . ? C84 C85 C86 120.3(3) . . ? C85 C86 C81 119.7(3) . . ? N88 C87 C81 110.2(2) . . ? N88 C87 C95 111.2(2) . . ? C81 C87 C95 110.7(3) . . ? C90 C89 C94 118.8(3) . . ? C90 C89 C95 119.9(3) . . ? C94 C89 C95 121.2(3) . . ? C89 C90 C91 120.5(4) . . ? C92 C91 C90 120.5(4) . . ? C91 C92 C93 119.7(3) . . ? C92 C93 C94 120.1(4) . . ? C89 C94 C93 120.3(4) . . ? N96 C95 C89 110.4(2) . . ? N96 C95 C87 111.3(2) . . ? C89 C95 C87 109.7(2) . . ? O202 C202 C203 102.9(5) . . ? O202 C202 C201 98.3(6) . . ? C203 C202 C201 108.5(6) . . ? C202 C203 C204 113.0(5) . . ? C205 C204 C203 112.5(5) . . ? C204 C205 C206 113.3(6) . . ? C207 C206 C205 113.8(7) . . ? C213 C212 C211 113.0(11) . . ? C213 C212 O212 89.6(9) . . ? C211 C212 O212 108.5(10) . . ? C212 C213 C214 121.6(12) . . ? C215 C214 C213 125.6(13) . . ? C214 C215 C216 124.8(14) . . ? C215 C216 C217 97.5(12) . . ? O302 C302 C303 111.8(6) . . ? O302 C302 C301 104.8(5) . . ? C303 C302 C301 111.6(7) . . ? C304 C303 C302 114.5(5) . . ? C303 C304 C305 116.9(5) . . ? C306 C305 C304 113.7(5) . . ? C307 C306 C305 117.9(6) . . ? O312 C312 C313 107.5(14) . . ? O312 C312 C311 105.9(13) . . ? C313 C312 C311 106.2(13) . . ? C312 C313 C314 110.7(13) . . ? C315 C314 C313 121.7(14) . . ? C314 C315 C316 122.6(14) . . ? C317 C316 C315 117.7(15) . . ? 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 C201 C203 C202 O202 103.5(7) . . . . ? C211 C213 C212 O212 -110.0(13) . . . . ? C301 C303 C302 O302 -117.0(10) . . . . ? C311 C313 C312 O312 112.9(19) . . . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 27.94 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.473 _refine_diff_density_min -0.319 _refine_diff_density_rms 0.056 #===END