Electronic Supplementary Material for CrystEngComm This journal is (c) The Royal Society of Chemistry 2006 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Agata Bialonska' _publ_contact_author_address ; Faculty of Chemistry University of Wroclaw 14. F. Curie-Joliot Wroclaw 50-383 POLAND ; _publ_contact_author_email BIALONSK@WCHETO.CHEM.UNI.WROC.PL _publ_section_title ; When in the presence of the strong hydrogen bonds, the weak hydrogen bonds gain an importance. ; loop_ _publ_author_name 'Agata Bialonska' 'Zbigniew Ciunik' # Attachment 'cif 4.txt' data_4 _database_code_depnum_ccdc_archive 'CCDC 203141' _audit_creation_method SHELXL-97 _chemical_name_systematic ; brucinium N-tert-Butoxycarbonyl-L-prolinate ethanol solvate hydrate ; _chemical_name_common ;brucinium N-tert-Butoxycarbonyl-L-prolinate ethanol solvate hydrate ; _chemical_melting_point ? _chemical_formula_moiety 'C23 H27 N2 O4, C10 H16 N O4, C2 H6 O, H2 O' _chemical_formula_sum 'C35 H51 N3 O10' _chemical_formula_weight 673.79 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting MONOCLINIC _symmetry_space_group_name_H-M 'P 21' _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 7.5255(10) _cell_length_b 12.0556(15) _cell_length_c 18.597(2) _cell_angle_alpha 90.00 _cell_angle_beta 96.238(10) _cell_angle_gamma 90.00 _cell_volume 1677.2(4) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2562 _cell_measurement_theta_min 3.56 _cell_measurement_theta_max 26.67 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.334 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 724 _exptl_absorpt_coefficient_mu 0.098 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 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 'Kuma KM4CCD' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10422 _diffrn_reflns_av_R_equivalents 0.0546 _diffrn_reflns_av_sigmaI/netI 0.0498 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 3.56 _diffrn_reflns_theta_max 26.00 _reflns_number_total 3404 _reflns_number_gt 3002 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD (Oxford Diffraction,Poland Sp. z o.o)' _computing_cell_refinement 'CrysAlis RED (Oxford Diffraction,Poland Sp. z o.o)' _computing_data_reduction 'CrysAlis RED (Oxford Diffraction,Poland Sp. z o.o)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL-NT V5.1, Bruker AXS 1999' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0520P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _chemical_absolute_configuration rm _refine_ls_abs_structure_details 'from known structure (Toda et al., 1985)' _refine_ls_number_reflns 3404 _refine_ls_number_parameters 433 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0470 _refine_ls_R_factor_gt 0.0391 _refine_ls_wR_factor_ref 0.0899 _refine_ls_wR_factor_gt 0.0859 _refine_ls_goodness_of_fit_ref 1.022 _refine_ls_restrained_S_all 1.022 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.8747(2) 0.96885(16) 0.13530(10) 0.0181(4) Uani 1 1 d . . . O2 O 0.6893(2) 0.38766(16) -0.13785(10) 0.0172(4) Uani 1 1 d . . . O3 O 0.6951(3) 0.26832(15) -0.02074(10) 0.0190(4) Uani 1 1 d . . . O4 O 0.7478(3) 0.79844(16) -0.09019(10) 0.0219(4) Uani 1 1 d . . . N1 N 0.8552(3) 0.71563(18) 0.01599(12) 0.0150(5) Uani 1 1 d . . . N2 N 1.0043(3) 0.61142(19) 0.25364(12) 0.0172(5) Uani 1 1 d . . . H2 H 1.0330 0.5503 0.2831 0.021 Uiso 1 1 calc R . . C1 C 0.7705(4) 0.5569(2) -0.07037(15) 0.0161(6) Uani 1 1 d . . . H1 H 0.7593 0.6017 -0.1127 0.019 Uiso 1 1 calc R . . C2 C 0.7359(3) 0.4432(2) -0.07402(14) 0.0158(6) Uani 1 1 d . . . C3 C 0.7462(3) 0.3776(2) -0.01084(14) 0.0146(6) Uani 1 1 d . . . C4 C 0.8051(4) 0.4244(2) 0.05581(14) 0.0153(6) Uani 1 1 d . . . H4 H 0.8176 0.3801 0.0983 0.018 Uiso 1 1 calc R . . C5 C 0.8455(3) 0.5372(2) 0.05956(14) 0.0147(6) Uani 1 1 d . . . C6 C 0.8220(3) 0.6023(2) -0.00262(15) 0.0159(6) Uani 1 1 d . . . C7 C 0.9246(4) 0.6048(2) 0.12282(15) 0.0162(6) Uani 1 1 d . . . C8 C 0.8888(4) 0.7259(2) 0.09625(14) 0.0141(6) Uani 1 1 d . . . H8 H 0.9980 0.7720 0.1093 0.017 Uiso 1 1 calc R . . C9 C 0.7892(3) 0.8039(2) -0.02404(15) 0.0173(6) Uani 1 1 d . . . C10 C 0.7649(4) 0.9118(2) 0.01607(15) 0.0176(6) Uani 1 1 d . . . H10A H 0.6625 0.9518 -0.0100 0.021 Uiso 1 1 calc R . . H10B H 0.8726 0.9578 0.0126 0.021 Uiso 1 1 calc R . . C11 C 0.7328(4) 0.9056(2) 0.09708(15) 0.0163(6) Uani 1 1 d . . . H11 H 0.6161 0.9419 0.1034 0.020 Uiso 1 1 calc R . . C12 C 0.8527(4) 0.9919(2) 0.20971(15) 0.0192(6) Uani 1 1 d . . . H12A H 0.7240 1.0016 0.2147 0.023 Uiso 1 1 calc R . . H12B H 0.9145 1.0621 0.2244 0.023 Uiso 1 1 calc R . . C13 C 0.9266(4) 0.8997(2) 0.25920(15) 0.0178(6) Uani 1 1 d . . . H13 H 1.0215 0.9166 0.2955 0.021 Uiso 1 1 calc R . . C14 C 0.8656(4) 0.7960(2) 0.25452(15) 0.0185(6) Uani 1 1 d . . . C15 C 0.9521(4) 0.7046(2) 0.30081(15) 0.0195(6) Uani 1 1 d . . . H15A H 1.0595 0.7334 0.3304 0.023 Uiso 1 1 calc R . . H15B H 0.8678 0.6768 0.3340 0.023 Uiso 1 1 calc R . . C16 C 1.1656(4) 0.6394(2) 0.21546(15) 0.0187(6) Uani 1 1 d . . . H16A H 1.2761 0.6092 0.2422 0.022 Uiso 1 1 calc R . . H16B H 1.1786 0.7207 0.2106 0.022 Uiso 1 1 calc R . . C17 C 1.1283(4) 0.5848(2) 0.14173(14) 0.0164(6) Uani 1 1 d . . . H17A H 1.1564 0.5046 0.1443 0.020 Uiso 1 1 calc R . . H17B H 1.1980 0.6203 0.1058 0.020 Uiso 1 1 calc R . . C18 C 0.7259(3) 0.7841(2) 0.12160(14) 0.0148(6) Uani 1 1 d . . . H18 H 0.6187 0.7506 0.0932 0.018 Uiso 1 1 calc R . . C19 C 0.7065(4) 0.7605(2) 0.20129(14) 0.0157(6) Uani 1 1 d . . . H19 H 0.5968 0.7988 0.2145 0.019 Uiso 1 1 calc R . . C20 C 0.6800(4) 0.6346(2) 0.20758(15) 0.0180(6) Uani 1 1 d . . . H20A H 0.6462 0.6160 0.2561 0.022 Uiso 1 1 calc R . . H20B H 0.5830 0.6096 0.1709 0.022 Uiso 1 1 calc R . . C21 C 0.8541(4) 0.5770(2) 0.19552(14) 0.0159(6) Uani 1 1 d . . . H21 H 0.8364 0.4950 0.1984 0.019 Uiso 1 1 calc R . . C22 C 0.6780(4) 0.4533(2) -0.20247(15) 0.0202(6) Uani 1 1 d . . . H22A H 0.6441 0.4058 -0.2445 0.030 Uiso 1 1 calc R . . H22B H 0.7944 0.4875 -0.2071 0.030 Uiso 1 1 calc R . . H22C H 0.5879 0.5114 -0.2000 0.030 Uiso 1 1 calc R . . C23 C 0.6872(4) 0.2043(2) 0.04386(15) 0.0237(6) Uani 1 1 d . . . H23A H 0.6495 0.1284 0.0309 0.035 Uiso 1 1 calc R . . H23B H 0.6012 0.2380 0.0732 0.035 Uiso 1 1 calc R . . H23C H 0.8057 0.2027 0.0716 0.035 Uiso 1 1 calc R . . O5 O 1.1232(3) 0.42391(17) 0.31256(11) 0.0253(5) Uani 1 1 d . . . O6 O 1.2795(3) 0.54164(18) 0.38727(12) 0.0325(5) Uani 1 1 d . . . O7 O 1.2274(3) 0.08901(16) 0.33303(11) 0.0258(5) Uani 1 1 d . . . O8 O 1.1827(3) 0.21719(16) 0.42077(10) 0.0235(5) Uani 1 1 d . . . N3 N 1.3711(3) 0.25527(19) 0.34047(13) 0.0216(6) Uani 1 1 d . . . C24 C 1.2570(4) 0.4494(2) 0.35696(16) 0.0214(6) Uani 1 1 d . . . C25 C 1.4078(4) 0.3636(2) 0.37385(16) 0.0221(6) Uani 1 1 d . . . H25 H 1.4345 0.3549 0.4274 0.026 Uiso 1 1 calc R . . C26 C 1.5776(4) 0.3995(3) 0.34123(17) 0.0274(7) Uani 1 1 d . . . H26A H 1.5859 0.4814 0.3386 0.033 Uiso 1 1 calc R . . H26B H 1.6861 0.3705 0.3700 0.033 Uiso 1 1 calc R . . C27 C 1.5537(5) 0.3480(3) 0.26549(18) 0.0314(8) Uani 1 1 d . . . H27A H 1.4762 0.3949 0.2315 0.038 Uiso 1 1 calc R . . H27B H 1.6706 0.3382 0.2464 0.038 Uiso 1 1 calc R . . C28 C 1.4658(4) 0.2359(3) 0.27656(16) 0.0242(7) Uani 1 1 d . . . H28A H 1.3815 0.2155 0.2340 0.029 Uiso 1 1 calc R . . H28B H 1.5565 0.1766 0.2857 0.029 Uiso 1 1 calc R . . C29 C 1.2569(4) 0.1787(2) 0.36192(16) 0.0218(6) Uani 1 1 d . . . C30 C 1.0400(4) 0.1542(2) 0.45041(17) 0.0251(7) Uani 1 1 d . . . C31 C 0.9824(5) 0.2343(3) 0.50659(18) 0.0324(8) Uani 1 1 d . . . H31A H 1.0820 0.2465 0.5443 0.049 Uiso 1 1 calc R . . H31B H 0.8806 0.2030 0.5284 0.049 Uiso 1 1 calc R . . H31C H 0.9473 0.3051 0.4833 0.049 Uiso 1 1 calc R . . C32 C 1.1143(5) 0.0486(3) 0.4851(2) 0.0434(9) Uani 1 1 d . . . H32A H 1.2128 0.0664 0.5222 0.065 Uiso 1 1 calc R . . H32B H 1.1586 0.0010 0.4482 0.065 Uiso 1 1 calc R . . H32C H 1.0200 0.0097 0.5074 0.065 Uiso 1 1 calc R . . C33 C 0.8865(4) 0.1348(3) 0.39181(19) 0.0359(8) Uani 1 1 d . . . H33A H 0.9244 0.0832 0.3558 0.054 Uiso 1 1 calc R . . H33B H 0.8512 0.2055 0.3684 0.054 Uiso 1 1 calc R . . H33C H 0.7847 0.1033 0.4134 0.054 Uiso 1 1 calc R . . O34 O 1.4699(5) 0.7283(2) 0.35676(14) 0.0654(9) Uani 1 1 d . . . H34 H 1.4151 0.6651 0.3686 0.098 Uiso 1 1 d R . . C34 C 1.4797(5) 0.7958(3) 0.4168(2) 0.0417(9) Uani 1 1 d . . . H34A H 1.5432 0.7562 0.4586 0.050 Uiso 1 1 calc R . . H34B H 1.3572 0.8125 0.4285 0.050 Uiso 1 1 calc R . . C35 C 1.5750(5) 0.9022(3) 0.40500(18) 0.0332(8) Uani 1 1 d . . . H35A H 1.5789 0.9480 0.4487 0.050 Uiso 1 1 calc R . . H35B H 1.5113 0.9422 0.3641 0.050 Uiso 1 1 calc R . . H35C H 1.6971 0.8859 0.3945 0.050 Uiso 1 1 calc R . . O1W O 1.0002(3) 0.28027(18) 0.19935(11) 0.0305(5) Uani 1 1 d . . . H11W H 1.0593 0.3162 0.2400 0.046 Uiso 1 1 d R . . H12W H 1.0781 0.2812 0.1705 0.046 Uiso 1 1 d R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0176(10) 0.0164(10) 0.0210(10) -0.0028(8) 0.0056(8) -0.0024(8) O2 0.0209(10) 0.0173(10) 0.0138(10) -0.0009(8) 0.0035(8) -0.0001(8) O3 0.0234(11) 0.0121(10) 0.0213(11) -0.0002(8) 0.0018(8) -0.0013(8) O4 0.0300(11) 0.0193(11) 0.0160(10) 0.0019(8) 0.0006(8) 0.0008(9) N1 0.0166(12) 0.0143(12) 0.0141(11) -0.0002(9) 0.0018(9) 0.0000(9) N2 0.0196(12) 0.0151(13) 0.0174(12) -0.0004(9) 0.0046(9) -0.0007(9) C1 0.0149(14) 0.0159(15) 0.0177(14) 0.0039(11) 0.0026(11) 0.0029(11) C2 0.0116(13) 0.0190(15) 0.0169(14) -0.0044(11) 0.0024(11) 0.0019(11) C3 0.0143(13) 0.0113(14) 0.0186(15) -0.0019(11) 0.0034(11) -0.0016(10) C4 0.0149(14) 0.0153(14) 0.0158(13) 0.0023(11) 0.0015(10) 0.0026(11) C5 0.0124(14) 0.0167(14) 0.0157(14) 0.0005(11) 0.0038(11) 0.0013(11) C6 0.0118(14) 0.0124(14) 0.0240(15) 0.0002(11) 0.0043(11) 0.0005(10) C7 0.0182(14) 0.0119(14) 0.0186(14) -0.0008(11) 0.0031(11) 0.0015(11) C8 0.0144(14) 0.0142(14) 0.0146(13) 0.0018(11) 0.0056(10) 0.0005(11) C9 0.0118(14) 0.0163(15) 0.0246(16) 0.0023(12) 0.0054(11) -0.0007(11) C10 0.0198(15) 0.0141(14) 0.0189(14) 0.0009(11) 0.0023(11) -0.0005(11) C11 0.0142(14) 0.0142(14) 0.0209(14) 0.0001(11) 0.0042(11) 0.0007(11) C12 0.0202(15) 0.0164(14) 0.0216(15) -0.0053(12) 0.0054(11) -0.0015(11) C13 0.0171(14) 0.0191(15) 0.0179(14) -0.0058(11) 0.0052(11) -0.0005(11) C14 0.0158(14) 0.0227(16) 0.0178(14) -0.0004(12) 0.0058(11) 0.0018(12) C15 0.0247(15) 0.0156(14) 0.0186(15) -0.0020(12) 0.0034(11) 0.0005(12) C16 0.0174(14) 0.0183(15) 0.0208(15) 0.0004(12) 0.0043(11) 0.0006(11) C17 0.0156(14) 0.0142(14) 0.0195(14) 0.0019(11) 0.0025(11) 0.0014(10) C18 0.0143(14) 0.0120(13) 0.0185(14) -0.0011(11) 0.0039(10) 0.0014(11) C19 0.0154(14) 0.0155(14) 0.0175(14) -0.0005(11) 0.0074(11) 0.0010(10) C20 0.0195(14) 0.0167(14) 0.0189(15) 0.0018(11) 0.0067(11) -0.0010(12) C21 0.0180(14) 0.0145(14) 0.0150(14) 0.0015(11) 0.0015(11) -0.0024(11) C22 0.0234(16) 0.0204(15) 0.0167(14) 0.0005(12) 0.0017(11) 0.0000(12) C23 0.0321(17) 0.0157(15) 0.0238(16) 0.0034(13) 0.0060(13) -0.0018(13) O5 0.0270(12) 0.0223(11) 0.0254(11) 0.0012(9) -0.0027(9) 0.0010(9) O6 0.0435(14) 0.0194(12) 0.0330(13) -0.0083(10) -0.0023(11) 0.0044(10) O7 0.0315(12) 0.0159(11) 0.0310(12) -0.0051(9) 0.0078(9) -0.0039(9) O8 0.0322(11) 0.0183(11) 0.0214(11) 0.0003(8) 0.0090(9) -0.0037(9) N3 0.0245(14) 0.0145(12) 0.0268(13) -0.0013(10) 0.0079(11) -0.0020(10) C24 0.0299(17) 0.0163(15) 0.0185(14) 0.0023(12) 0.0053(12) 0.0004(12) C25 0.0273(16) 0.0151(15) 0.0235(16) 0.0010(12) 0.0016(12) 0.0002(12) C26 0.0253(17) 0.0243(17) 0.0326(18) 0.0018(14) 0.0040(13) -0.0053(13) C27 0.0313(18) 0.0285(18) 0.0367(19) 0.0012(15) 0.0137(15) -0.0024(14) C28 0.0243(16) 0.0247(17) 0.0239(16) 0.0003(13) 0.0041(12) 0.0021(13) C29 0.0222(15) 0.0194(16) 0.0235(16) 0.0028(13) 0.0013(12) 0.0017(12) C30 0.0302(17) 0.0194(16) 0.0276(17) 0.0016(13) 0.0110(13) -0.0054(12) C31 0.0404(19) 0.0319(19) 0.0265(17) -0.0041(14) 0.0110(14) -0.0072(15) C32 0.052(2) 0.030(2) 0.051(2) 0.0156(18) 0.0201(19) 0.0024(17) C33 0.0293(18) 0.0352(19) 0.044(2) -0.0121(17) 0.0083(16) -0.0028(15) O34 0.112(3) 0.0465(18) 0.0410(16) -0.0185(14) 0.0247(16) -0.0373(17) C34 0.047(2) 0.035(2) 0.046(2) -0.0104(17) 0.0148(17) -0.0147(17) C35 0.0345(19) 0.0333(19) 0.0321(18) -0.0004(15) 0.0058(14) -0.0023(15) O1W 0.0326(13) 0.0322(13) 0.0269(12) -0.0012(10) 0.0031(9) -0.0029(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C11 1.436(3) . ? O1 C12 1.439(3) . ? O2 C2 1.375(3) . ? O2 C22 1.433(3) . ? O3 C3 1.379(3) . ? O3 C23 1.434(3) . ? O4 C9 1.238(3) . ? N1 C9 1.361(4) . ? N1 C6 1.425(3) . ? N1 C8 1.492(3) . ? N2 C15 1.503(3) . ? N2 C16 1.510(3) . ? N2 C21 1.534(3) . ? N2 H2 0.9300 . ? C1 C6 1.389(4) . ? C1 C2 1.396(4) . ? C1 H1 0.9500 . ? C2 C3 1.412(4) . ? C3 C4 1.390(4) . ? C4 C5 1.393(4) . ? C4 H4 0.9500 . ? C5 C6 1.393(4) . ? C5 C7 1.500(4) . ? C7 C21 1.542(4) . ? C7 C17 1.554(4) . ? C7 C8 1.555(4) . ? C8 C18 1.531(3) . ? C8 H8 1.0000 . ? C9 C10 1.521(4) . ? C10 C11 1.553(4) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C18 1.536(4) . ? C11 H11 1.0000 . ? C12 C13 1.510(4) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.332(4) . ? C13 H13 0.9500 . ? C14 C15 1.503(4) . ? C14 C19 1.529(4) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 C17 1.519(4) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 C19 1.532(4) . ? C18 H18 1.0000 . ? C19 C20 1.536(4) . ? C19 H19 1.0000 . ? C20 C21 1.521(4) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C21 H21 1.0000 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? O5 C24 1.268(4) . ? O6 C24 1.250(3) . ? O7 C29 1.217(3) . ? O8 C29 1.363(3) . ? O8 C30 1.470(3) . ? N3 C29 1.351(4) . ? N3 C25 1.460(4) . ? N3 C28 1.469(4) . ? C24 C25 1.542(4) . ? C25 C26 1.535(4) . ? C25 H25 1.0000 . ? C26 C27 1.532(4) . ? C26 H26A 0.9900 . ? C26 H26B 0.9900 . ? C27 C28 1.528(4) . ? C27 H27A 0.9900 . ? C27 H27B 0.9900 . ? C28 H28A 0.9900 . ? C28 H28B 0.9900 . ? C30 C32 1.507(5) . ? C30 C33 1.518(4) . ? C30 C31 1.520(4) . ? C31 H31A 0.9800 . ? C31 H31B 0.9800 . ? C31 H31C 0.9800 . ? C32 H32A 0.9800 . ? C32 H32B 0.9800 . ? C32 H32C 0.9800 . ? C33 H33A 0.9800 . ? C33 H33B 0.9800 . ? C33 H33C 0.9800 . ? O34 C34 1.377(4) . ? O34 H34 0.9039 . ? C34 C35 1.497(5) . ? C34 H34A 0.9900 . ? C34 H34B 0.9900 . ? C35 H35A 0.9800 . ? C35 H35B 0.9800 . ? C35 H35C 0.9800 . ? O1W H11W 0.9405 . ? O1W H12W 0.8362 . ? 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 C11 O1 C12 114.9(2) . . ? C2 O2 C22 116.2(2) . . ? C3 O3 C23 116.0(2) . . ? C9 N1 C6 125.0(2) . . ? C9 N1 C8 119.6(2) . . ? C6 N1 C8 109.2(2) . . ? C15 N2 C16 112.5(2) . . ? C15 N2 C21 113.2(2) . . ? C16 N2 C21 107.3(2) . . ? C15 N2 H2 107.9 . . ? C16 N2 H2 107.9 . . ? C21 N2 H2 107.9 . . ? C6 C1 C2 117.6(2) . . ? C6 C1 H1 121.2 . . ? C2 C1 H1 121.2 . . ? O2 C2 C1 123.3(2) . . ? O2 C2 C3 115.6(2) . . ? C1 C2 C3 121.1(2) . . ? O3 C3 C4 124.4(2) . . ? O3 C3 C2 115.8(2) . . ? C4 C3 C2 119.8(2) . . ? C3 C4 C5 119.2(3) . . ? C3 C4 H4 120.4 . . ? C5 C4 H4 120.4 . . ? C6 C5 C4 120.1(3) . . ? C6 C5 C7 110.4(2) . . ? C4 C5 C7 129.4(3) . . ? C1 C6 C5 121.9(2) . . ? C1 C6 N1 128.4(2) . . ? C5 C6 N1 109.6(2) . . ? C5 C7 C21 115.1(2) . . ? C5 C7 C17 113.0(2) . . ? C21 C7 C17 101.1(2) . . ? C5 C7 C8 102.7(2) . . ? C21 C7 C8 114.7(2) . . ? C17 C7 C8 110.5(2) . . ? N1 C8 C18 107.0(2) . . ? N1 C8 C7 104.2(2) . . ? C18 C8 C7 116.7(2) . . ? N1 C8 H8 109.6 . . ? C18 C8 H8 109.6 . . ? C7 C8 H8 109.6 . . ? O4 C9 N1 122.7(3) . . ? O4 C9 C10 120.1(2) . . ? N1 C9 C10 117.2(2) . . ? C9 C10 C11 118.3(2) . . ? C9 C10 H10A 107.7 . . ? C11 C10 H10A 107.7 . . ? C9 C10 H10B 107.7 . . ? C11 C10 H10B 107.7 . . ? H10A C10 H10B 107.1 . . ? O1 C11 C18 114.0(2) . . ? O1 C11 C10 105.6(2) . . ? C18 C11 C10 110.4(2) . . ? O1 C11 H11 108.9 . . ? C18 C11 H11 108.9 . . ? C10 C11 H11 108.9 . . ? O1 C12 C13 111.8(2) . . ? O1 C12 H12A 109.3 . . ? C13 C12 H12A 109.3 . . ? O1 C12 H12B 109.3 . . ? C13 C12 H12B 109.3 . . ? H12A C12 H12B 107.9 . . ? C14 C13 C12 123.3(3) . . ? C14 C13 H13 118.4 . . ? C12 C13 H13 118.4 . . ? C13 C14 C15 121.8(3) . . ? C13 C14 C19 123.1(3) . . ? C15 C14 C19 115.2(2) . . ? N2 C15 C14 109.8(2) . . ? N2 C15 H15A 109.7 . . ? C14 C15 H15A 109.7 . . ? N2 C15 H15B 109.7 . . ? C14 C15 H15B 109.7 . . ? H15A C15 H15B 108.2 . . ? N2 C16 C17 104.4(2) . . ? N2 C16 H16A 110.9 . . ? C17 C16 H16A 110.9 . . ? N2 C16 H16B 110.9 . . ? C17 C16 H16B 110.9 . . ? H16A C16 H16B 108.9 . . ? C16 C17 C7 102.6(2) . . ? C16 C17 H17A 111.2 . . ? C7 C17 H17A 111.2 . . ? C16 C17 H17B 111.2 . . ? C7 C17 H17B 111.2 . . ? H17A C17 H17B 109.2 . . ? C8 C18 C19 112.1(2) . . ? C8 C18 C11 107.0(2) . . ? C19 C18 C11 118.3(2) . . ? C8 C18 H18 106.2 . . ? C19 C18 H18 106.2 . . ? C11 C18 H18 106.2 . . ? C14 C19 C18 115.1(2) . . ? C14 C19 C20 109.1(2) . . ? C18 C19 C20 106.5(2) . . ? C14 C19 H19 108.7 . . ? C18 C19 H19 108.7 . . ? C20 C19 H19 108.7 . . ? C21 C20 C19 108.6(2) . . ? C21 C20 H20A 110.0 . . ? C19 C20 H20A 110.0 . . ? C21 C20 H20B 110.0 . . ? C19 C20 H20B 110.0 . . ? H20A C20 H20B 108.4 . . ? C20 C21 N2 110.7(2) . . ? C20 C21 C7 114.5(2) . . ? N2 C21 C7 105.2(2) . . ? C20 C21 H21 108.8 . . ? N2 C21 H21 108.8 . . ? C7 C21 H21 108.8 . . ? O2 C22 H22A 109.5 . . ? O2 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? O2 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? O3 C23 H23A 109.5 . . ? O3 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? O3 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C29 O8 C30 120.3(2) . . ? C29 N3 C25 125.6(3) . . ? C29 N3 C28 120.7(2) . . ? C25 N3 C28 113.6(2) . . ? O6 C24 O5 124.6(3) . . ? O6 C24 C25 116.3(3) . . ? O5 C24 C25 119.0(2) . . ? N3 C25 C26 102.2(2) . . ? N3 C25 C24 114.4(2) . . ? C26 C25 C24 110.9(2) . . ? N3 C25 H25 109.7 . . ? C26 C25 H25 109.7 . . ? C24 C25 H25 109.7 . . ? C27 C26 C25 103.3(2) . . ? C27 C26 H26A 111.1 . . ? C25 C26 H26A 111.1 . . ? C27 C26 H26B 111.1 . . ? C25 C26 H26B 111.1 . . ? H26A C26 H26B 109.1 . . ? C28 C27 C26 104.1(3) . . ? C28 C27 H27A 110.9 . . ? C26 C27 H27A 110.9 . . ? C28 C27 H27B 110.9 . . ? C26 C27 H27B 110.9 . . ? H27A C27 H27B 108.9 . . ? N3 C28 C27 102.9(2) . . ? N3 C28 H28A 111.2 . . ? C27 C28 H28A 111.2 . . ? N3 C28 H28B 111.2 . . ? C27 C28 H28B 111.2 . . ? H28A C28 H28B 109.1 . . ? O7 C29 N3 124.6(3) . . ? O7 C29 O8 125.9(3) . . ? N3 C29 O8 109.5(2) . . ? O8 C30 C32 110.2(3) . . ? O8 C30 C33 109.9(2) . . ? C32 C30 C33 113.3(3) . . ? O8 C30 C31 101.8(2) . . ? C32 C30 C31 111.3(3) . . ? C33 C30 C31 109.8(3) . . ? C30 C31 H31A 109.5 . . ? C30 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? C30 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? C30 C32 H32A 109.5 . . ? C30 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C30 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? C30 C33 H33A 109.5 . . ? C30 C33 H33B 109.5 . . ? H33A C33 H33B 109.5 . . ? C30 C33 H33C 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? C34 O34 H34 106.6 . . ? O34 C34 C35 111.8(3) . . ? O34 C34 H34A 109.2 . . ? C35 C34 H34A 109.2 . . ? O34 C34 H34B 109.2 . . ? C35 C34 H34B 109.2 . . ? H34A C34 H34B 107.9 . . ? C34 C35 H35A 109.5 . . ? C34 C35 H35B 109.5 . . ? H35A C35 H35B 109.5 . . ? C34 C35 H35C 109.5 . . ? H35A C35 H35C 109.5 . . ? H35B C35 H35C 109.5 . . ? H11W O1W H12W 101.9 . . ? 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 C22 O2 C2 C1 0.2(4) . . . . ? C22 O2 C2 C3 179.9(2) . . . . ? C6 C1 C2 O2 -177.9(2) . . . . ? C6 C1 C2 C3 2.4(4) . . . . ? C23 O3 C3 C4 6.3(4) . . . . ? C23 O3 C3 C2 -173.7(2) . . . . ? O2 C2 C3 O3 -4.8(3) . . . . ? C1 C2 C3 O3 174.9(2) . . . . ? O2 C2 C3 C4 175.2(2) . . . . ? C1 C2 C3 C4 -5.0(4) . . . . ? O3 C3 C4 C5 -177.1(2) . . . . ? C2 C3 C4 C5 2.9(4) . . . . ? C3 C4 C5 C6 1.8(4) . . . . ? C3 C4 C5 C7 -174.4(3) . . . . ? C2 C1 C6 C5 2.4(4) . . . . ? C2 C1 C6 N1 -176.3(3) . . . . ? C4 C5 C6 C1 -4.6(4) . . . . ? C7 C5 C6 C1 172.3(2) . . . . ? C4 C5 C6 N1 174.3(2) . . . . ? C7 C5 C6 N1 -8.8(3) . . . . ? C9 N1 C6 C1 22.3(4) . . . . ? C8 N1 C6 C1 174.2(3) . . . . ? C9 N1 C6 C5 -156.5(2) . . . . ? C8 N1 C6 C5 -4.6(3) . . . . ? C6 C5 C7 C21 143.0(2) . . . . ? C4 C5 C7 C21 -40.5(4) . . . . ? C6 C5 C7 C17 -101.5(3) . . . . ? C4 C5 C7 C17 75.0(4) . . . . ? C6 C5 C7 C8 17.6(3) . . . . ? C4 C5 C7 C8 -165.9(3) . . . . ? C9 N1 C8 C18 44.7(3) . . . . ? C6 N1 C8 C18 -109.0(2) . . . . ? C9 N1 C8 C7 168.8(2) . . . . ? C6 N1 C8 C7 15.2(3) . . . . ? C5 C7 C8 N1 -19.1(3) . . . . ? C21 C7 C8 N1 -144.8(2) . . . . ? C17 C7 C8 N1 101.7(2) . . . . ? C5 C7 C8 C18 98.5(3) . . . . ? C21 C7 C8 C18 -27.2(3) . . . . ? C17 C7 C8 C18 -140.7(2) . . . . ? C6 N1 C9 O4 -26.0(4) . . . . ? C8 N1 C9 O4 -175.3(2) . . . . ? C6 N1 C9 C10 153.2(2) . . . . ? C8 N1 C9 C10 4.0(3) . . . . ? O4 C9 C10 C11 152.4(2) . . . . ? N1 C9 C10 C11 -26.8(4) . . . . ? C12 O1 C11 C18 -69.9(3) . . . . ? C12 O1 C11 C10 168.7(2) . . . . ? C9 C10 C11 O1 121.8(2) . . . . ? C9 C10 C11 C18 -1.8(3) . . . . ? C11 O1 C12 C13 87.3(3) . . . . ? O1 C12 C13 C14 -61.3(3) . . . . ? C12 C13 C14 C15 175.0(2) . . . . ? C12 C13 C14 C19 -3.7(4) . . . . ? C16 N2 C15 C14 73.9(3) . . . . ? C21 N2 C15 C14 -48.0(3) . . . . ? C13 C14 C15 N2 -124.3(3) . . . . ? C19 C14 C15 N2 54.4(3) . . . . ? C15 N2 C16 C17 -143.6(2) . . . . ? C21 N2 C16 C17 -18.5(3) . . . . ? N2 C16 C17 C7 38.7(3) . . . . ? C5 C7 C17 C16 -167.3(2) . . . . ? C21 C7 C17 C16 -43.7(3) . . . . ? C8 C7 C17 C16 78.2(3) . . . . ? N1 C8 C18 C19 157.6(2) . . . . ? C7 C8 C18 C19 41.5(3) . . . . ? N1 C8 C18 C11 -71.2(2) . . . . ? C7 C8 C18 C11 172.7(2) . . . . ? O1 C11 C18 C8 -69.9(3) . . . . ? C10 C11 C18 C8 48.7(3) . . . . ? O1 C11 C18 C19 57.8(3) . . . . ? C10 C11 C18 C19 176.4(2) . . . . ? C13 C14 C19 C18 57.2(4) . . . . ? C15 C14 C19 C18 -121.6(2) . . . . ? C13 C14 C19 C20 176.8(2) . . . . ? C15 C14 C19 C20 -2.0(3) . . . . ? C8 C18 C19 C14 59.3(3) . . . . ? C11 C18 C19 C14 -65.9(3) . . . . ? C8 C18 C19 C20 -61.7(3) . . . . ? C11 C18 C19 C20 173.1(2) . . . . ? C14 C19 C20 C21 -55.6(3) . . . . ? C18 C19 C20 C21 69.2(3) . . . . ? C19 C20 C21 N2 61.9(3) . . . . ? C19 C20 C21 C7 -56.8(3) . . . . ? C15 N2 C21 C20 -8.5(3) . . . . ? C16 N2 C21 C20 -133.2(2) . . . . ? C15 N2 C21 C7 115.6(2) . . . . ? C16 N2 C21 C7 -9.1(3) . . . . ? C5 C7 C21 C20 -84.0(3) . . . . ? C17 C7 C21 C20 153.9(2) . . . . ? C8 C7 C21 C20 35.0(3) . . . . ? C5 C7 C21 N2 154.3(2) . . . . ? C17 C7 C21 N2 32.2(3) . . . . ? C8 C7 C21 N2 -86.7(3) . . . . ? C29 N3 C25 C26 165.8(3) . . . . ? C28 N3 C25 C26 -16.9(3) . . . . ? C29 N3 C25 C24 -74.3(4) . . . . ? C28 N3 C25 C24 103.0(3) . . . . ? O6 C24 C25 N3 176.8(2) . . . . ? O5 C24 C25 N3 -5.3(4) . . . . ? O6 C24 C25 C26 -68.4(3) . . . . ? O5 C24 C25 C26 109.6(3) . . . . ? N3 C25 C26 C27 32.7(3) . . . . ? C24 C25 C26 C27 -89.6(3) . . . . ? C25 C26 C27 C28 -37.4(3) . . . . ? C29 N3 C28 C27 171.3(3) . . . . ? C25 N3 C28 C27 -6.1(3) . . . . ? C26 C27 C28 N3 26.8(3) . . . . ? C25 N3 C29 O7 179.5(3) . . . . ? C28 N3 C29 O7 2.4(4) . . . . ? C25 N3 C29 O8 -1.1(4) . . . . ? C28 N3 C29 O8 -178.2(2) . . . . ? C30 O8 C29 O7 -6.7(4) . . . . ? C30 O8 C29 N3 173.9(2) . . . . ? C29 O8 C30 C32 69.6(4) . . . . ? C29 O8 C30 C33 -56.0(3) . . . . ? C29 O8 C30 C31 -172.3(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2 O5 0.93 1.73 2.626(3) 160.3 . N2 H2 O6 0.93 2.53 3.171(3) 125.9 . O34 H34 O6 0.90 1.86 2.759(4) 173.6 . O1W H11W O5 0.94 1.90 2.804(3) 161.6 . O1W H12W O4 0.84 2.10 2.933(3) 172.5 2_745 _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 0.171 _refine_diff_density_min -0.239 _refine_diff_density_rms 0.045 # Attachment 'cif 1.txt' data_1 _database_code_depnum_ccdc_archive 'CCDC 288082' _audit_creation_method SHELXL-97 _chemical_name_systematic ; brucinium hydrogen N-benzoyl-D-aspartate tetrahydrate ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C23 H27 N2 O4, C11 H10 N O5, 4(H2 O)' _chemical_formula_sum 'C34 H45 N3 O13' _chemical_formula_weight 703.73 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' 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 8.2334(14) _cell_length_b 12.283(2) _cell_length_c 33.625(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3400.6(9) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2364 _cell_measurement_theta_min 3.32 _cell_measurement_theta_max 28.06 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.375 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1496 _exptl_absorpt_coefficient_mu 0.106 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 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 'Kuma KM4CCD' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 22753 _diffrn_reflns_av_R_equivalents 0.1173 _diffrn_reflns_av_sigmaI/netI 0.0949 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -43 _diffrn_reflns_limit_l_max 43 _diffrn_reflns_theta_min 3.32 _diffrn_reflns_theta_max 27.50 _reflns_number_total 4313 _reflns_number_gt 2955 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD (Oxford Diffraction, Poland Sp. z o.o)' _computing_cell_refinement 'CrysAlis RED (Oxford Diffraction, Poland Sp. z o.o)' _computing_data_reduction 'CrysAlis RED (Oxford Diffraction, Poland Sp. z o.o)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL-NT V5.1, Bruker AXS 1999' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0926P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _chemical_absolute_configuration rm _refine_ls_abs_structure_details 'from known structure (Toda et al., 1985)' _refine_ls_number_reflns 4313 _refine_ls_number_parameters 451 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1192 _refine_ls_R_factor_gt 0.0776 _refine_ls_wR_factor_ref 0.1882 _refine_ls_wR_factor_gt 0.1642 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.052 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.7521(5) 1.0261(3) 0.68759(11) 0.0360(9) Uani 1 1 d . . . O2 O 0.7054(5) 0.4384(3) 0.83099(10) 0.0341(9) Uani 1 1 d . . . O3 O 0.7492(5) 0.3264(3) 0.76676(10) 0.0338(9) Uani 1 1 d . . . O4 O 0.7021(5) 0.8399(3) 0.80889(11) 0.0391(10) Uani 1 1 d . . . N1 N 0.6516(6) 0.7686(3) 0.74751(13) 0.0303(10) Uani 1 1 d . . . N2 N 0.6566(6) 0.6892(4) 0.61486(13) 0.0349(11) Uani 1 1 d . . . H2 H 0.6427 0.6326 0.5968 0.042 Uiso 1 1 calc R . . C1 C 0.6715(6) 0.6082(4) 0.79461(15) 0.0270(11) Uani 1 1 d . . . H1 H 0.6604 0.6505 0.8181 0.032 Uiso 1 1 calc R . . C2 C 0.6961(7) 0.4964(4) 0.79630(15) 0.0305(12) Uani 1 1 d . . . C3 C 0.7152(6) 0.4345(4) 0.76116(16) 0.0304(12) Uani 1 1 d . . . C4 C 0.7011(6) 0.4845(4) 0.72451(14) 0.0271(11) Uani 1 1 d . . . H4 H 0.7091 0.4427 0.7008 0.033 Uiso 1 1 calc R . . C5 C 0.6753(7) 0.5962(4) 0.72242(15) 0.0303(12) Uani 1 1 d . . . C6 C 0.6639(6) 0.6559(4) 0.75690(15) 0.0282(11) Uani 1 1 d . . . C7 C 0.6467(6) 0.6669(4) 0.68641(14) 0.0273(11) Uani 1 1 d . . . C8 C 0.6734(7) 0.7838(4) 0.70381(15) 0.0303(12) Uani 1 1 d . . . H8 H 0.5887 0.8345 0.6933 0.036 Uiso 1 1 calc R . . C9 C 0.6973(7) 0.8505(4) 0.77295(17) 0.0334(12) Uani 1 1 d . . . C10 C 0.7392(7) 0.9574(4) 0.75248(15) 0.0306(12) Uani 1 1 d . . . H10A H 0.8030 1.0020 0.7714 0.037 Uiso 1 1 calc R . . H10B H 0.6365 0.9968 0.7473 0.037 Uiso 1 1 calc R . . C11 C 0.8355(7) 0.9513(4) 0.71272(16) 0.0334(12) Uani 1 1 d . . . H11 H 0.9487 0.9781 0.7173 0.040 Uiso 1 1 calc R . . C12 C 0.8286(8) 1.0458(4) 0.65014(17) 0.0407(14) Uani 1 1 d . . . H12A H 0.9479 1.0407 0.6534 0.049 Uiso 1 1 calc R . . H12B H 0.8023 1.1204 0.6411 0.049 Uiso 1 1 calc R . . C13 C 0.7743(7) 0.9656(5) 0.61929(16) 0.0378(14) Uani 1 1 d . . . H13 H 0.7160 0.9909 0.5967 0.045 Uiso 1 1 calc R . . C14 C 0.8061(7) 0.8592(5) 0.62277(16) 0.0341(13) Uani 1 1 d . . . C15 C 0.7394(8) 0.7791(5) 0.59299(15) 0.0355(13) Uani 1 1 d . . . H15A H 0.6612 0.8160 0.5751 0.043 Uiso 1 1 calc R . . H15B H 0.8288 0.7493 0.5766 0.043 Uiso 1 1 calc R . . C16 C 0.4900(7) 0.7189(5) 0.62994(17) 0.0360(13) Uani 1 1 d . . . H16A H 0.4050 0.6956 0.6109 0.043 Uiso 1 1 calc R . . H16B H 0.4809 0.7985 0.6342 0.043 Uiso 1 1 calc R . . C17 C 0.4744(7) 0.6578(5) 0.66913(17) 0.0353(13) Uani 1 1 d . . . H17A H 0.4435 0.5808 0.6647 0.042 Uiso 1 1 calc R . . H17B H 0.3934 0.6925 0.6868 0.042 Uiso 1 1 calc R . . C18 C 0.8424(7) 0.8328(4) 0.69774(16) 0.0322(12) Uani 1 1 d . . . H18 H 0.9159 0.7932 0.7165 0.039 Uiso 1 1 calc R . . C19 C 0.9108(7) 0.8133(4) 0.65648(17) 0.0336(13) Uani 1 1 d . . . H19 H 1.0221 0.8456 0.6548 0.040 Uiso 1 1 calc R . . C20 C 0.9225(7) 0.6894(5) 0.65106(18) 0.0367(13) Uani 1 1 d . . . H20A H 0.9794 0.6724 0.6259 0.044 Uiso 1 1 calc R . . H20B H 0.9851 0.6571 0.6733 0.044 Uiso 1 1 calc R . . C21 C 0.7552(7) 0.6423(5) 0.65025(16) 0.0342(13) Uani 1 1 d . . . H21 H 0.7636 0.5616 0.6470 0.041 Uiso 1 1 calc R . . C22 C 0.6844(8) 0.4976(5) 0.86722(16) 0.0397(14) Uani 1 1 d . . . H22A H 0.6930 0.4475 0.8898 0.060 Uiso 1 1 calc R . . H22B H 0.5771 0.5321 0.8674 0.060 Uiso 1 1 calc R . . H22C H 0.7686 0.5537 0.8693 0.060 Uiso 1 1 calc R . . C23 C 0.7724(8) 0.2625(4) 0.73128(17) 0.0409(14) Uani 1 1 d . . . H23A H 0.7965 0.1870 0.7386 0.061 Uiso 1 1 calc R . . H23B H 0.8631 0.2925 0.7159 0.061 Uiso 1 1 calc R . . H23C H 0.6732 0.2647 0.7152 0.061 Uiso 1 1 calc R . . O5 O 0.5633(5) 0.5639(3) 0.55718(13) 0.0445(10) Uani 1 1 d . . . O6 O 0.8195(5) 0.5168(3) 0.55128(12) 0.0391(10) Uani 1 1 d . . . O7 O 0.7822(7) 0.6947(4) 0.48711(16) 0.0649(14) Uani 1 1 d . . . O8 O 0.6096(6) 0.7419(3) 0.44016(14) 0.0510(12) Uani 1 1 d . . . H87 H 0.6663 0.8055 0.4410 0.061 Uiso 1 1 d R . . O9 O 0.6243(5) 0.3071(3) 0.44581(13) 0.0412(10) Uani 1 1 d . . . N3 N 0.7765(6) 0.4332(4) 0.47733(14) 0.0368(11) Uani 1 1 d . . . H37 H 0.8736 0.4611 0.4812 0.044 Uiso 1 1 calc R . . C24 C 0.6802(7) 0.5235(4) 0.53877(16) 0.0326(12) Uani 1 1 d . . . C25 C 0.6362(7) 0.4831(5) 0.49675(17) 0.0341(13) Uani 1 1 d . . . H25 H 0.5525 0.4247 0.5000 0.041 Uiso 1 1 calc R . . C26 C 0.5600(8) 0.5723(5) 0.47064(17) 0.0389(14) Uani 1 1 d . . . H26A H 0.5395 0.5418 0.4438 0.047 Uiso 1 1 calc R . . H26B H 0.4538 0.5931 0.4822 0.047 Uiso 1 1 calc R . . C27 C 0.6629(7) 0.6733(5) 0.46637(18) 0.0391(14) Uani 1 1 d . . . C28 C 0.7605(7) 0.3455(4) 0.45364(16) 0.0330(12) Uani 1 1 d . . . C29 C 0.9124(7) 0.2970(4) 0.43759(16) 0.0301(12) Uani 1 1 d . . . C30 C 0.9036(7) 0.2387(4) 0.40225(16) 0.0334(13) Uani 1 1 d . . . H30 H 0.8011 0.2289 0.3898 0.040 Uiso 1 1 calc R . . C31 C 1.0414(8) 0.1943(5) 0.38479(19) 0.0415(14) Uani 1 1 d . . . H31 H 1.0331 0.1546 0.3606 0.050 Uiso 1 1 calc R . . C32 C 1.1902(8) 0.2083(5) 0.40281(18) 0.0429(15) Uani 1 1 d . . . H32 H 1.2851 0.1797 0.3906 0.051 Uiso 1 1 calc R . . C33 C 1.2027(7) 0.2637(5) 0.43858(18) 0.0397(14) Uani 1 1 d . . . H33 H 1.3050 0.2706 0.4514 0.048 Uiso 1 1 calc R . . C34 C 1.0631(7) 0.3093(5) 0.45563(18) 0.0366(13) Uani 1 1 d . . . H34 H 1.0716 0.3491 0.4798 0.044 Uiso 1 1 calc R . . O1W O 1.0045(6) 0.4241(4) 0.65764(13) 0.0557(13) Uani 1 1 d . . . H11W H 1.0332 0.4160 0.6331 0.084 Uiso 1 1 d R . . H12W H 1.0874 0.4083 0.6728 0.084 Uiso 1 1 d R . . O2W O 1.2458(5) 0.5702(3) 0.54984(14) 0.0526(12) Uani 1 1 d . . . H21W H 1.3502 0.5595 0.5483 0.079 Uiso 1 1 d R . . H22W H 1.2031 0.5174 0.5634 0.079 Uiso 1 1 d R . . O3W O 1.0708(5) 0.4019(3) 0.57586(12) 0.0442(11) Uani 1 1 d . . . H31W H 0.9826 0.4242 0.5652 0.066 Uiso 1 1 d R . . H32W H 1.0839 0.3343 0.5699 0.066 Uiso 1 1 d R . . O4W O 1.0676(6) 0.5728(4) 0.47800(14) 0.0536(12) Uani 1 1 d . . . H41W H 0.9934 0.6216 0.4834 0.080 Uiso 1 1 d R . . H42W H 1.1307 0.5660 0.4988 0.080 Uiso 1 1 d R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.045(2) 0.030(2) 0.033(2) 0.0039(17) 0.0010(18) 0.0026(18) O2 0.049(2) 0.0269(19) 0.0264(18) 0.0030(16) -0.0001(17) 0.0041(18) O3 0.048(2) 0.0219(18) 0.0311(19) -0.0008(16) 0.0054(17) 0.0036(17) O4 0.060(3) 0.031(2) 0.027(2) -0.0003(17) -0.0028(18) -0.0090(19) N1 0.046(3) 0.018(2) 0.027(2) -0.0020(18) -0.003(2) 0.001(2) N2 0.049(3) 0.029(2) 0.027(2) 0.002(2) -0.001(2) 0.002(2) C1 0.032(3) 0.024(2) 0.025(3) 0.000(2) -0.003(2) -0.003(2) C2 0.039(3) 0.029(3) 0.023(3) -0.001(2) 0.002(2) 0.003(2) C3 0.032(3) 0.022(2) 0.038(3) 0.003(2) -0.004(2) 0.001(2) C4 0.037(3) 0.024(2) 0.021(2) -0.004(2) 0.002(2) -0.005(2) C5 0.034(3) 0.027(3) 0.029(3) 0.001(2) 0.001(2) -0.004(2) C6 0.030(3) 0.024(2) 0.031(3) -0.003(2) 0.006(2) -0.006(2) C7 0.034(3) 0.026(3) 0.022(2) 0.003(2) 0.003(2) 0.001(2) C8 0.038(3) 0.027(3) 0.026(3) -0.003(2) 0.007(2) 0.000(2) C9 0.038(3) 0.025(3) 0.037(3) 0.001(2) -0.002(3) -0.003(2) C10 0.043(3) 0.019(2) 0.030(3) -0.003(2) -0.005(2) 0.000(2) C11 0.038(3) 0.024(3) 0.038(3) 0.005(2) 0.001(2) -0.001(2) C12 0.058(4) 0.026(3) 0.039(3) 0.006(3) 0.002(3) 0.004(3) C13 0.044(4) 0.040(3) 0.030(3) 0.007(3) 0.003(3) 0.000(3) C14 0.038(3) 0.029(3) 0.036(3) 0.001(2) 0.006(3) 0.000(2) C15 0.050(4) 0.038(3) 0.019(2) 0.004(2) 0.001(2) 0.000(3) C16 0.040(3) 0.032(3) 0.036(3) -0.002(3) -0.001(2) 0.004(3) C17 0.040(3) 0.028(3) 0.037(3) 0.000(3) -0.001(3) 0.002(2) C18 0.038(3) 0.026(3) 0.033(3) 0.002(2) -0.002(2) 0.000(2) C19 0.032(3) 0.026(3) 0.043(3) 0.006(3) 0.007(2) 0.001(2) C20 0.045(4) 0.029(3) 0.036(3) -0.002(3) 0.007(3) -0.003(3) C21 0.042(3) 0.028(3) 0.032(3) -0.001(2) 0.005(3) 0.003(3) C22 0.057(4) 0.028(3) 0.034(3) 0.000(2) 0.008(3) -0.004(3) C23 0.060(4) 0.025(3) 0.038(3) -0.008(3) 0.007(3) 0.005(3) O5 0.042(2) 0.043(2) 0.048(2) -0.008(2) 0.001(2) 0.006(2) O6 0.038(2) 0.039(2) 0.041(2) -0.0023(18) -0.0065(19) 0.0010(19) O7 0.069(3) 0.041(3) 0.084(3) 0.011(3) -0.033(3) -0.009(3) O8 0.057(3) 0.037(2) 0.059(3) 0.011(2) -0.011(2) -0.004(2) O9 0.035(2) 0.039(2) 0.050(3) -0.007(2) 0.0030(18) -0.0018(19) N3 0.036(3) 0.029(2) 0.045(3) -0.007(2) 0.005(2) -0.003(2) C24 0.039(3) 0.027(3) 0.032(3) 0.004(2) 0.005(3) 0.000(2) C25 0.033(3) 0.030(3) 0.039(3) -0.001(3) -0.001(2) 0.001(2) C26 0.051(4) 0.039(3) 0.026(3) -0.001(3) -0.007(3) 0.005(3) C27 0.039(3) 0.036(3) 0.042(3) 0.007(3) -0.010(3) -0.003(3) C28 0.037(3) 0.028(3) 0.034(3) -0.002(2) 0.001(2) 0.007(3) C29 0.038(3) 0.020(2) 0.033(3) 0.005(2) 0.005(2) 0.001(2) C30 0.042(3) 0.025(3) 0.034(3) 0.003(2) 0.002(2) 0.000(2) C31 0.045(4) 0.038(3) 0.041(3) 0.003(3) 0.010(3) 0.006(3) C32 0.051(4) 0.036(3) 0.042(3) 0.013(3) 0.009(3) 0.012(3) C33 0.032(3) 0.037(3) 0.050(4) 0.011(3) -0.002(3) -0.003(3) C34 0.036(3) 0.031(3) 0.043(3) -0.001(3) 0.000(3) 0.002(3) O1W 0.067(3) 0.059(3) 0.041(3) -0.010(2) -0.003(2) 0.011(3) O2W 0.037(2) 0.040(2) 0.081(3) 0.008(2) -0.004(2) -0.004(2) O3W 0.048(3) 0.031(2) 0.053(3) -0.005(2) 0.001(2) 0.004(2) O4W 0.053(3) 0.052(3) 0.057(3) -0.002(2) 0.000(2) -0.009(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C11 1.426(6) . ? O1 C12 1.429(7) . ? O2 C2 1.369(6) . ? O2 C22 1.429(6) . ? O3 C3 1.370(6) . ? O3 C23 1.440(6) . ? O4 C9 1.216(6) . ? N1 C9 1.373(7) . ? N1 C6 1.424(6) . ? N1 C8 1.492(6) . ? N2 C15 1.492(7) . ? N2 C16 1.508(8) . ? N2 C21 1.551(7) . ? N2 H2 0.9300 . ? C1 C2 1.389(7) . ? C1 C6 1.398(7) . ? C1 H1 0.9500 . ? C2 C3 1.414(7) . ? C3 C4 1.382(7) . ? C4 C5 1.390(7) . ? C4 H4 0.9500 . ? C5 C6 1.375(7) . ? C5 C7 1.509(7) . ? C7 C17 1.538(8) . ? C7 C21 1.538(7) . ? C7 C8 1.565(7) . ? C8 C18 1.529(8) . ? C8 H8 1.0000 . ? C9 C10 1.522(7) . ? C10 C11 1.556(8) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C18 1.541(7) . ? C11 H11 1.0000 . ? C12 C13 1.499(8) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.337(7) . ? C13 H13 0.9500 . ? C14 C15 1.508(8) . ? C14 C19 1.532(8) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 C17 1.523(8) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 C19 1.517(8) . ? C18 H18 1.0000 . ? C19 C20 1.537(8) . ? C19 H19 1.0000 . ? C20 C21 1.494(8) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C21 H21 1.0000 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? O5 C24 1.247(7) . ? O6 C24 1.224(7) . ? O7 C27 1.233(7) . ? O8 C27 1.296(7) . ? O8 H87 0.9099 . ? O9 C28 1.244(7) . ? N3 C28 1.347(7) . ? N3 C25 1.462(7) . ? N3 H37 0.8800 . ? C24 C25 1.541(8) . ? C25 C26 1.537(8) . ? C25 H25 1.0000 . ? C26 C27 1.509(8) . ? C26 H26A 0.9900 . ? C26 H26B 0.9900 . ? C28 C29 1.487(8) . ? C29 C30 1.390(8) . ? C29 C34 1.389(8) . ? C30 C31 1.389(8) . ? C30 H30 0.9500 . ? C31 C32 1.377(9) . ? C31 H31 0.9500 . ? C32 C33 1.386(9) . ? C32 H32 0.9500 . ? C33 C34 1.401(8) . ? C33 H33 0.9500 . ? C34 H34 0.9500 . ? O1W H11W 0.8653 . ? O1W H12W 0.8725 . ? O2W H21W 0.8711 . ? O2W H22W 0.8669 . ? O3W H31W 0.8548 . ? O3W H32W 0.8607 . ? O4W H41W 0.8745 . ? O4W H42W 0.8742 . ? 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 C11 O1 C12 114.7(4) . . ? C2 O2 C22 117.1(4) . . ? C3 O3 C23 116.2(4) . . ? C9 N1 C6 123.7(4) . . ? C9 N1 C8 119.3(4) . . ? C6 N1 C8 109.4(4) . . ? C15 N2 C16 113.7(4) . . ? C15 N2 C21 114.5(4) . . ? C16 N2 C21 107.9(4) . . ? C15 N2 H2 106.8 . . ? C16 N2 H2 106.8 . . ? C21 N2 H2 106.8 . . ? C2 C1 C6 117.2(5) . . ? C2 C1 H1 121.4 . . ? C6 C1 H1 121.4 . . ? O2 C2 C1 123.9(5) . . ? O2 C2 C3 115.2(4) . . ? C1 C2 C3 120.9(5) . . ? O3 C3 C4 124.8(5) . . ? O3 C3 C2 115.4(4) . . ? C4 C3 C2 119.8(5) . . ? C3 C4 C5 119.8(5) . . ? C3 C4 H4 120.1 . . ? C5 C4 H4 120.1 . . ? C6 C5 C4 119.6(5) . . ? C6 C5 C7 111.1(5) . . ? C4 C5 C7 129.3(5) . . ? C5 C6 C1 122.6(5) . . ? C5 C6 N1 109.6(4) . . ? C1 C6 N1 127.7(4) . . ? C5 C7 C17 113.9(5) . . ? C5 C7 C21 115.5(4) . . ? C17 C7 C21 102.9(4) . . ? C5 C7 C8 101.9(4) . . ? C17 C7 C8 109.8(4) . . ? C21 C7 C8 113.2(4) . . ? N1 C8 C18 106.9(4) . . ? N1 C8 C7 103.7(4) . . ? C18 C8 C7 116.0(4) . . ? N1 C8 H8 110.0 . . ? C18 C8 H8 110.0 . . ? C7 C8 H8 110.0 . . ? O4 C9 N1 123.3(5) . . ? O4 C9 C10 122.3(5) . . ? N1 C9 C10 114.3(5) . . ? C9 C10 C11 117.6(4) . . ? C9 C10 H10A 107.9 . . ? C11 C10 H10A 107.9 . . ? C9 C10 H10B 107.9 . . ? C11 C10 H10B 107.9 . . ? H10A C10 H10B 107.2 . . ? O1 C11 C18 115.7(4) . . ? O1 C11 C10 103.4(4) . . ? C18 C11 C10 110.2(4) . . ? O1 C11 H11 109.1 . . ? C18 C11 H11 109.1 . . ? C10 C11 H11 109.1 . . ? O1 C12 C13 111.6(5) . . ? O1 C12 H12A 109.3 . . ? C13 C12 H12A 109.3 . . ? O1 C12 H12B 109.3 . . ? C13 C12 H12B 109.3 . . ? H12A C12 H12B 108.0 . . ? C14 C13 C12 121.5(5) . . ? C14 C13 H13 119.2 . . ? C12 C13 H13 119.2 . . ? C13 C14 C15 120.6(5) . . ? C13 C14 C19 122.3(5) . . ? C15 C14 C19 117.1(5) . . ? N2 C15 C14 108.8(4) . . ? N2 C15 H15A 109.9 . . ? C14 C15 H15A 109.9 . . ? N2 C15 H15B 109.9 . . ? C14 C15 H15B 109.9 . . ? H15A C15 H15B 108.3 . . ? N2 C16 C17 104.4(4) . . ? N2 C16 H16A 110.9 . . ? C17 C16 H16A 110.9 . . ? N2 C16 H16B 110.9 . . ? C17 C16 H16B 110.9 . . ? H16A C16 H16B 108.9 . . ? C16 C17 C7 102.3(5) . . ? C16 C17 H17A 111.3 . . ? C7 C17 H17A 111.3 . . ? C16 C17 H17B 111.3 . . ? C7 C17 H17B 111.3 . . ? H17A C17 H17B 109.2 . . ? C19 C18 C8 113.4(5) . . ? C19 C18 C11 117.5(4) . . ? C8 C18 C11 107.2(5) . . ? C19 C18 H18 106.0 . . ? C8 C18 H18 106.0 . . ? C11 C18 H18 106.0 . . ? C18 C19 C14 114.2(5) . . ? C18 C19 C20 106.7(4) . . ? C14 C19 C20 108.2(5) . . ? C18 C19 H19 109.2 . . ? C14 C19 H19 109.2 . . ? C20 C19 H19 109.2 . . ? C21 C20 C19 109.1(5) . . ? C21 C20 H20A 109.9 . . ? C19 C20 H20A 109.9 . . ? C21 C20 H20B 109.9 . . ? C19 C20 H20B 109.9 . . ? H20A C20 H20B 108.3 . . ? C20 C21 C7 116.4(5) . . ? C20 C21 N2 110.7(4) . . ? C7 C21 N2 103.3(4) . . ? C20 C21 H21 108.7 . . ? C7 C21 H21 108.7 . . ? N2 C21 H21 108.7 . . ? O2 C22 H22A 109.5 . . ? O2 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? O2 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? O3 C23 H23A 109.5 . . ? O3 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? O3 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C27 O8 H87 111.2 . . ? C28 N3 C25 121.5(5) . . ? C28 N3 H37 119.3 . . ? C25 N3 H37 119.3 . . ? O6 C24 O5 125.4(5) . . ? O6 C24 C25 120.9(5) . . ? O5 C24 C25 113.7(5) . . ? N3 C25 C26 111.4(5) . . ? N3 C25 C24 111.0(5) . . ? C26 C25 C24 113.0(5) . . ? N3 C25 H25 107.0 . . ? C26 C25 H25 107.0 . . ? C24 C25 H25 107.0 . . ? C27 C26 C25 114.3(5) . . ? C27 C26 H26A 108.7 . . ? C25 C26 H26A 108.7 . . ? C27 C26 H26B 108.7 . . ? C25 C26 H26B 108.7 . . ? H26A C26 H26B 107.6 . . ? O7 C27 O8 121.1(6) . . ? O7 C27 C26 124.6(5) . . ? O8 C27 C26 114.2(5) . . ? O9 C28 N3 121.1(5) . . ? O9 C28 C29 122.0(5) . . ? N3 C28 C29 116.9(5) . . ? C30 C29 C34 118.4(5) . . ? C30 C29 C28 118.2(5) . . ? C34 C29 C28 123.3(5) . . ? C31 C30 C29 121.4(6) . . ? C31 C30 H30 119.3 . . ? C29 C30 H30 119.3 . . ? C32 C31 C30 119.4(6) . . ? C32 C31 H31 120.3 . . ? C30 C31 H31 120.3 . . ? C31 C32 C33 120.6(6) . . ? C31 C32 H32 119.7 . . ? C33 C32 H32 119.7 . . ? C32 C33 C34 119.4(6) . . ? C32 C33 H33 120.3 . . ? C34 C33 H33 120.3 . . ? C29 C34 C33 120.7(6) . . ? C29 C34 H34 119.7 . . ? C33 C34 H34 119.7 . . ? H11W O1W H12W 108.5 . . ? H21W O2W H22W 108.7 . . ? H31W O3W H32W 108.5 . . ? H41W O4W H42W 108.4 . . ? 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 C22 O2 C2 C1 1.5(8) . . . . ? C22 O2 C2 C3 -179.1(5) . . . . ? C6 C1 C2 O2 -179.6(5) . . . . ? C6 C1 C2 C3 1.0(8) . . . . ? C23 O3 C3 C4 0.4(8) . . . . ? C23 O3 C3 C2 -178.8(5) . . . . ? O2 C2 C3 O3 -3.4(7) . . . . ? C1 C2 C3 O3 175.9(5) . . . . ? O2 C2 C3 C4 177.3(5) . . . . ? C1 C2 C3 C4 -3.3(8) . . . . ? O3 C3 C4 C5 -176.4(5) . . . . ? C2 C3 C4 C5 2.8(8) . . . . ? C3 C4 C5 C6 -0.1(8) . . . . ? C3 C4 C5 C7 -176.1(5) . . . . ? C4 C5 C6 C1 -2.3(9) . . . . ? C7 C5 C6 C1 174.4(5) . . . . ? C4 C5 C6 N1 175.1(5) . . . . ? C7 C5 C6 N1 -8.2(6) . . . . ? C2 C1 C6 C5 1.8(8) . . . . ? C2 C1 C6 N1 -175.1(5) . . . . ? C9 N1 C6 C5 -155.1(5) . . . . ? C8 N1 C6 C5 -6.1(6) . . . . ? C9 N1 C6 C1 22.1(9) . . . . ? C8 N1 C6 C1 171.1(5) . . . . ? C6 C5 C7 C17 -100.1(6) . . . . ? C4 C5 C7 C17 76.2(7) . . . . ? C6 C5 C7 C21 141.2(5) . . . . ? C4 C5 C7 C21 -42.5(8) . . . . ? C6 C5 C7 C8 18.0(6) . . . . ? C4 C5 C7 C8 -165.6(6) . . . . ? C9 N1 C8 C18 44.4(6) . . . . ? C6 N1 C8 C18 -106.2(5) . . . . ? C9 N1 C8 C7 167.5(5) . . . . ? C6 N1 C8 C7 16.9(6) . . . . ? C5 C7 C8 N1 -20.2(5) . . . . ? C17 C7 C8 N1 100.8(5) . . . . ? C21 C7 C8 N1 -144.9(4) . . . . ? C5 C7 C8 C18 96.6(5) . . . . ? C17 C7 C8 C18 -142.3(5) . . . . ? C21 C7 C8 C18 -28.0(6) . . . . ? C6 N1 C9 O4 -24.7(9) . . . . ? C8 N1 C9 O4 -170.8(5) . . . . ? C6 N1 C9 C10 156.3(5) . . . . ? C8 N1 C9 C10 10.2(7) . . . . ? O4 C9 C10 C11 141.3(6) . . . . ? N1 C9 C10 C11 -39.7(7) . . . . ? C12 O1 C11 C18 -66.5(6) . . . . ? C12 O1 C11 C10 172.9(4) . . . . ? C9 C10 C11 O1 134.8(5) . . . . ? C9 C10 C11 C18 10.6(7) . . . . ? C11 O1 C12 C13 88.4(6) . . . . ? O1 C12 C13 C14 -64.0(8) . . . . ? C12 C13 C14 C15 175.3(5) . . . . ? C12 C13 C14 C19 -5.0(9) . . . . ? C16 N2 C15 C14 78.0(6) . . . . ? C21 N2 C15 C14 -46.7(6) . . . . ? C13 C14 C15 N2 -129.0(6) . . . . ? C19 C14 C15 N2 51.2(6) . . . . ? C15 N2 C16 C17 -145.5(5) . . . . ? C21 N2 C16 C17 -17.4(6) . . . . ? N2 C16 C17 C7 37.8(5) . . . . ? C5 C7 C17 C16 -169.9(4) . . . . ? C21 C7 C17 C16 -44.1(5) . . . . ? C8 C7 C17 C16 76.6(5) . . . . ? N1 C8 C18 C19 157.4(4) . . . . ? C7 C8 C18 C19 42.4(6) . . . . ? N1 C8 C18 C11 -71.2(5) . . . . ? C7 C8 C18 C11 173.7(4) . . . . ? O1 C11 C18 C19 54.7(7) . . . . ? C10 C11 C18 C19 171.6(5) . . . . ? O1 C11 C18 C8 -74.3(6) . . . . ? C10 C11 C18 C8 42.5(6) . . . . ? C8 C18 C19 C14 59.0(6) . . . . ? C11 C18 C19 C14 -67.0(7) . . . . ? C8 C18 C19 C20 -60.5(6) . . . . ? C11 C18 C19 C20 173.4(5) . . . . ? C13 C14 C19 C18 61.7(7) . . . . ? C15 C14 C19 C18 -118.6(5) . . . . ? C13 C14 C19 C20 -179.6(6) . . . . ? C15 C14 C19 C20 0.1(7) . . . . ? C18 C19 C20 C21 66.6(6) . . . . ? C14 C19 C20 C21 -56.7(6) . . . . ? C19 C20 C21 C7 -56.2(6) . . . . ? C19 C20 C21 N2 61.3(6) . . . . ? C5 C7 C21 C20 -81.0(6) . . . . ? C17 C7 C21 C20 154.4(5) . . . . ? C8 C7 C21 C20 36.0(7) . . . . ? C5 C7 C21 N2 157.6(4) . . . . ? C17 C7 C21 N2 32.9(5) . . . . ? C8 C7 C21 N2 -85.5(5) . . . . ? C15 N2 C21 C20 -7.4(6) . . . . ? C16 N2 C21 C20 -135.1(5) . . . . ? C15 N2 C21 C7 117.8(5) . . . . ? C16 N2 C21 C7 -9.8(5) . . . . ? C28 N3 C25 C26 -90.1(6) . . . . ? C28 N3 C25 C24 143.0(5) . . . . ? O6 C24 C25 N3 3.4(7) . . . . ? O5 C24 C25 N3 -177.9(5) . . . . ? O6 C24 C25 C26 -122.6(6) . . . . ? O5 C24 C25 C26 56.0(7) . . . . ? N3 C25 C26 C27 -69.9(6) . . . . ? C24 C25 C26 C27 55.9(7) . . . . ? C25 C26 C27 O7 -13.2(9) . . . . ? C25 C26 C27 O8 171.0(5) . . . . ? C25 N3 C28 O9 3.7(9) . . . . ? C25 N3 C28 C29 -176.0(5) . . . . ? O9 C28 C29 C30 25.7(8) . . . . ? N3 C28 C29 C30 -154.6(5) . . . . ? O9 C28 C29 C34 -156.0(6) . . . . ? N3 C28 C29 C34 23.8(8) . . . . ? C34 C29 C30 C31 -0.7(8) . . . . ? C28 C29 C30 C31 177.8(5) . . . . ? C29 C30 C31 C32 0.0(8) . . . . ? C30 C31 C32 C33 1.7(9) . . . . ? C31 C32 C33 C34 -2.5(9) . . . . ? C30 C29 C34 C33 -0.2(8) . . . . ? C28 C29 C34 C33 -178.5(5) . . . . ? C32 C33 C34 C29 1.7(9) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2 O5 0.93 1.71 2.592(6) 157.8 . N2 H2 O6 0.93 2.55 3.294(6) 137.7 . O8 H87 O2W 0.91 1.69 2.588(6) 168.5 4_466 N3 H37 O4W 0.88 2.11 2.948(7) 159.2 . O1W H11W O3W 0.87 1.96 2.817(6) 173.1 . O1W H12W O4 0.87 2.02 2.859(6) 160.1 3_746 O2W H21W O5 0.87 1.78 2.627(6) 163.2 1_655 O2W H22W O3W 0.87 1.84 2.667(6) 159.7 . O3W H31W O6 0.85 1.82 2.637(6) 159.2 . O3W H32W O9 0.86 1.85 2.705(6) 175.5 4_556 O4W H41W O7 0.87 1.96 2.803(7) 161.1 . O4W H42W O2W 0.87 1.96 2.826(7) 169.6 . _diffrn_measured_fraction_theta_max 0.977 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.977 _refine_diff_density_max 0.271 _refine_diff_density_min -0.287 _refine_diff_density_rms 0.066 # Attachment 'cif 2.txt' data_2 _database_code_depnum_ccdc_archive 'CCDC 288083' _audit_creation_method SHELXL-97 _chemical_name_systematic ; brucinium N-benzoyl-D-asparaginate trihydrate ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C23 H27 N2 O4, C11 H11 N2 O4, 3(H2 O)' _chemical_formula_sum 'C34 H44 N4 O11' _chemical_formula_weight 684.73 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 7.8711(8) _cell_length_b 12.4649(12) _cell_length_c 33.044(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3242.0(6) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 1926 _cell_measurement_theta_min 3.06 _cell_measurement_theta_max 28.30 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.403 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1456 _exptl_absorpt_coefficient_mu 0.105 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 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 'Kuma KM4CCD' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 30873 _diffrn_reflns_av_R_equivalents 0.1278 _diffrn_reflns_av_sigmaI/netI 0.1341 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -42 _diffrn_reflns_limit_l_max 43 _diffrn_reflns_theta_min 3.06 _diffrn_reflns_theta_max 28.00 _reflns_number_total 4367 _reflns_number_gt 2109 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD (Oxford Diffraction, Poland Sp. z o.o)' _computing_cell_refinement 'CrysAlis RED (Oxford Diffraction, Poland Sp. z o.o)' _computing_data_reduction 'CrysAlis RED (Oxford Diffraction, Poland Sp. z o.o)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL-NT V5.1, Bruker AXS 1999' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0230P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _chemical_absolute_configuration rm _refine_ls_abs_structure_details 'from known structure (Toda et al., 1985)' _refine_ls_number_reflns 4367 _refine_ls_number_parameters 598 _refine_ls_number_restraints 450 _refine_ls_R_factor_all 0.1489 _refine_ls_R_factor_gt 0.0583 _refine_ls_wR_factor_ref 0.0867 _refine_ls_wR_factor_gt 0.0722 _refine_ls_goodness_of_fit_ref 1.005 _refine_ls_restrained_S_all 0.987 _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 O1 O 0.6869(3) -0.01764(11) 0.32066(5) 0.0431(6) Uani 1 1 d . . . O2 O 0.7574(3) 0.55608(11) 0.17338(5) 0.0380(6) Uani 1 1 d . . . O3 O 0.7796(2) 0.66855(10) 0.23903(5) 0.0371(5) Uani 1 1 d . . . O4 O 0.7306(2) 0.16114(11) 0.19656(5) 0.0404(6) Uani 1 1 d . . . N1 N 0.6531(3) 0.23373(12) 0.25702(6) 0.0250(6) Uani 1 1 d . . . N2 N 0.5759(3) 0.31981(14) 0.39068(6) 0.0412(7) Uani 1 1 d . . . H2 H 0.5566 0.3766 0.4083 0.049 Uiso 1 1 calc R . . C1 C 0.7021(3) 0.39037(15) 0.21027(7) 0.0264(7) Uani 1 1 d . . . H1 H 0.6991 0.3483 0.1863 0.032 Uiso 1 1 calc R . . C2 C 0.7336(4) 0.50024(17) 0.20858(8) 0.0307(8) Uani 1 1 d . . . C3 C 0.7399(3) 0.56148(15) 0.24445(7) 0.0274(8) Uani 1 1 d . . . C4 C 0.7056(3) 0.51438(16) 0.28128(8) 0.0262(8) Uani 1 1 d . . . H4 H 0.7052 0.5563 0.3053 0.031 Uiso 1 1 calc R . . C5 C 0.6713(3) 0.40466(16) 0.28298(7) 0.0223(7) Uani 1 1 d . . . C6 C 0.6756(3) 0.34448(16) 0.24763(8) 0.0249(7) Uani 1 1 d . . . C7 C 0.6174(3) 0.33567(16) 0.31866(7) 0.0247(7) Uani 1 1 d . . . C8 C 0.6470(3) 0.21951(16) 0.30217(8) 0.0304(8) Uani 1 1 d . . . H8 H 0.5486 0.1727 0.3096 0.036 Uiso 1 1 calc R . . C9 C 0.7099(4) 0.15184(17) 0.23302(8) 0.0320(8) Uani 1 1 d . . . C10 C 0.7413(4) 0.04518(16) 0.25478(7) 0.0303(8) Uani 1 1 d . . . H10A H 0.8254 0.0042 0.2387 0.036 Uiso 1 1 calc R . . H10B H 0.6338 0.0040 0.2543 0.036 Uiso 1 1 calc R . . C11 C 0.8046(4) 0.04832(17) 0.29905(8) 0.0381(9) Uani 1 1 d . . . H11 H 0.9206 0.0158 0.3006 0.046 Uiso 1 1 calc R . . C12 C 0.7356(5) -0.04169(17) 0.36177(8) 0.0571(11) Uani 1 1 d . . . H12A H 0.8610 -0.0456 0.3636 0.068 Uiso 1 1 calc R . . H12B H 0.6891 -0.1126 0.3695 0.068 Uiso 1 1 calc R . . C13 C 0.6715(5) 0.04202(19) 0.39060(8) 0.0568(11) Uani 1 1 d . . . H13 H 0.5943 0.0210 0.4112 0.068 Uiso 1 1 calc R . . C14 C 0.7177(4) 0.14343(18) 0.38850(8) 0.0462(9) Uani 1 1 d . . . C15 C 0.6395(5) 0.22715(19) 0.41571(8) 0.0532(11) Uani 1 1 d . . . H15A H 0.5440 0.1953 0.4311 0.064 Uiso 1 1 calc R . . H15B H 0.7253 0.2530 0.4353 0.064 Uiso 1 1 calc R . . C16 C 0.4095(4) 0.29671(19) 0.36939(8) 0.0391(9) Uani 1 1 d . . . H16A H 0.3929 0.2186 0.3657 0.047 Uiso 1 1 calc R . . H16B H 0.3123 0.3261 0.3849 0.047 Uiso 1 1 calc R . . C17 C 0.4278(4) 0.35253(18) 0.32913(7) 0.0319(8) Uani 1 1 d . . . H17A H 0.4002 0.4298 0.3314 0.038 Uiso 1 1 calc R . . H17B H 0.3533 0.3195 0.3084 0.038 Uiso 1 1 calc R . . C18 C 0.8116(4) 0.16588(16) 0.31455(8) 0.0338(8) Uani 1 1 d . . . H18 H 0.9042 0.2023 0.2990 0.041 Uiso 1 1 calc R . . C19 C 0.8511(4) 0.18338(17) 0.35953(9) 0.0449(10) Uani 1 1 d . . . H19 H 0.9613 0.1475 0.3660 0.054 Uiso 1 1 calc R . . C20 C 0.8728(4) 0.30593(18) 0.36513(9) 0.0416(9) Uani 1 1 d . . . H20A H 0.9162 0.3216 0.3926 0.050 Uiso 1 1 calc R . . H20B H 0.9553 0.3340 0.3452 0.050 Uiso 1 1 calc R . . C21 C 0.7021(4) 0.35870(17) 0.35910(8) 0.0321(8) Uani 1 1 d . . . H21 H 0.7161 0.4381 0.3620 0.038 Uiso 1 1 calc R . . C22 C 0.7464(5) 0.49353(19) 0.13690(8) 0.0529(11) Uani 1 1 d . . . H22A H 0.7663 0.5400 0.1134 0.079 Uiso 1 1 calc R . . H22B H 0.6331 0.4614 0.1349 0.079 Uiso 1 1 calc R . . H22C H 0.8323 0.4366 0.1375 0.079 Uiso 1 1 calc R . . C23 C 0.7872(3) 0.73351(11) 0.27527(5) 0.0446(10) Uani 1 1 d . . . H23A H 0.8157 0.8076 0.2680 0.067 Uiso 1 1 calc R . . H23B H 0.8745 0.7049 0.2935 0.067 Uiso 1 1 calc R . . H23C H 0.6767 0.7321 0.2889 0.067 Uiso 1 1 calc R . . O5 O 0.4912(3) 0.46667(11) 0.44597(5) 0.0637(17) Uani 0.50 1 d PRU A 1 O6 O 0.7746(3) 0.45763(11) 0.45458(5) 0.0709(18) Uani 0.50 1 d PRU A 1 O7 O 0.7775(3) 0.33179(11) 0.55044(5) 0.0676(16) Uani 0.50 1 d PRU A 1 O8 O 0.5759(3) 0.70423(11) 0.56110(5) 0.0427(13) Uani 0.50 1 d PRU A 1 N3 N 0.7548(3) 0.57728(11) 0.52352(5) 0.0569(13) Uani 0.50 1 d PRU A 1 H37 H 0.8635 0.5602 0.5105 0.050 Uiso 0.50 1 d P B 1 N4 N 0.5544(8) 0.2603(4) 0.52111(16) 0.066(2) Uani 0.50 1 d PU A 1 H47A H 0.6032 0.1968 0.5213 0.079 Uiso 0.50 1 calc PR A 1 H47B H 0.4520 0.2680 0.5108 0.079 Uiso 0.50 1 calc PR A 1 C24 C 0.6514(11) 0.4814(5) 0.4643(2) 0.0559(16) Uani 0.50 1 d PU A 1 C25 C 0.6180(10) 0.5309(4) 0.5091(2) 0.0547(13) Uani 0.50 1 d PU A 1 H25 H 0.5219 0.6027 0.5120 0.050 Uiso 0.50 1 d P C 1 C26 C 0.5403(9) 0.4505(4) 0.53560(19) 0.0537(15) Uani 0.50 1 d PU A 1 H26A H 0.4221 0.4377 0.5266 0.064 Uiso 0.50 1 calc PR A 1 H26B H 0.5357 0.4794 0.5635 0.064 Uiso 0.50 1 calc PR A 1 C27 C 0.6348(10) 0.3440(5) 0.5362(2) 0.0493(17) Uani 0.50 1 d PU A 1 C28 C 0.7098(9) 0.6674(4) 0.54968(18) 0.0433(15) Uani 0.50 1 d PU A 1 C29 C 0.8816(7) 0.7139(4) 0.56596(17) 0.0283(12) Uani 0.50 1 d PU A 1 C30 C 0.8673(7) 0.7717(3) 0.60204(17) 0.0294(14) Uani 0.50 1 d PU A 1 H30 H 0.7609 0.7798 0.6153 0.035 Uiso 0.50 1 calc PR A 1 C31 C 1.0179(7) 0.8179(4) 0.61814(18) 0.0289(13) Uani 0.50 1 d PU A 1 H31 H 1.0113 0.8559 0.6430 0.035 Uiso 0.50 1 calc PR A 1 C32 C 1.1776(7) 0.8097(4) 0.59851(17) 0.0265(13) Uani 0.50 1 d PU A 1 H32 H 1.2777 0.8417 0.6091 0.032 Uiso 0.50 1 calc PR A 1 C33 C 1.1773(7) 0.7496(4) 0.56161(17) 0.0298(13) Uani 0.50 1 d PU A 1 H33 H 1.2817 0.7407 0.5476 0.036 Uiso 0.50 1 calc PR A 1 C34 C 1.0285(7) 0.7028(4) 0.54499(18) 0.0256(14) Uani 0.50 1 d PU A 1 H34 H 1.0318 0.6650 0.5200 0.031 Uiso 0.50 1 calc PR A 1 O5A O 0.4928(7) 0.4638(3) 0.44350(14) 0.075(2) Uani 0.50 1 d PU D 2 O6A O 0.7685(7) 0.4590(3) 0.45537(13) 0.0669(19) Uani 0.50 1 d PU D 2 O7A O 0.6761(6) 0.3412(3) 0.55618(13) 0.0471(14) Uani 0.50 1 d PU D 2 O8A O 0.6638(5) 0.7036(3) 0.55901(13) 0.0399(14) Uani 0.50 1 d PU D 2 N3A N 0.7630(8) 0.5800(3) 0.52322(13) 0.0576(13) Uani 0.50 1 d PU D 2 H37A H 0.8503 0.5397 0.5165 0.069 Uiso 0.50 1 calc PR D 2 N4A N 0.4729(8) 0.2850(4) 0.51353(16) 0.0489(18) Uani 0.50 1 d PU D 2 H47C H 0.5156 0.2198 0.5135 0.059 Uiso 0.50 1 calc PR D 2 H47D H 0.3819 0.2996 0.4991 0.059 Uiso 0.50 1 calc PR D 2 C24A C 0.6063(12) 0.4883(5) 0.4660(2) 0.0495(16) Uani 0.50 1 d PU D 2 C25A C 0.5786(10) 0.5479(5) 0.5035(2) 0.0526(13) Uani 0.50 1 d PU D 2 H25A H 0.5130 0.6148 0.4975 0.063 Uiso 0.50 1 calc PR D 2 C26A C 0.4689(10) 0.4721(5) 0.5339(2) 0.0540(16) Uani 0.50 1 d PU D 2 H26C H 0.4580 0.5016 0.5605 0.065 Uiso 0.50 1 d P E 2 H26D H 0.3567 0.4661 0.5204 0.065 Uiso 0.50 1 d P F 2 C27A C 0.5474(10) 0.3631(5) 0.5359(2) 0.0491(16) Uani 0.50 1 d PU D 2 C28A C 0.7933(9) 0.6604(4) 0.54826(18) 0.0350(13) Uani 0.50 1 d PU D 2 C29A C 0.9649(8) 0.6974(4) 0.5614(2) 0.0284(14) Uani 0.50 1 d PU D 2 C30A C 0.9614(7) 0.7617(4) 0.59705(19) 0.0259(13) Uani 0.50 1 d PU D 2 H30A H 0.8593 0.7712 0.6120 0.031 Uiso 0.50 1 calc PR D 2 C31A C 1.1095(7) 0.8094(4) 0.6091(2) 0.0287(14) Uani 0.50 1 d PU D 2 H31A H 1.1093 0.8550 0.6322 0.034 Uiso 0.50 1 calc PR D 2 C32A C 1.2648(8) 0.7915(4) 0.58753(19) 0.0416(14) Uani 0.50 1 d PU D 2 H32A H 1.3679 0.8223 0.5969 0.050 Uiso 0.50 1 calc PR D 2 C33A C 1.2638(8) 0.7290(4) 0.55296(19) 0.0409(15) Uani 0.50 1 d PU D 2 H33A H 1.3650 0.7187 0.5378 0.049 Uiso 0.50 1 calc PR D 2 C34A C 1.1146(7) 0.6821(4) 0.54087(19) 0.0334(14) Uani 0.50 1 d PU D 2 H34A H 1.1148 0.6377 0.5175 0.040 Uiso 0.50 1 calc PR D 2 O1W O 1.0355(3) 0.54121(16) 0.35011(7) 0.0751(8) Uani 1 1 d . . . H11W H 1.1035 0.5795 0.3356 0.113 Uiso 1 1 d . . . H12W H 1.0742 0.5389 0.3743 0.113 Uiso 1 1 d . . . O2W O 1.1971(8) 0.4541(3) 0.47885(14) 0.097(2) Uani 0.50 1 d P G 1 H21W H 1.2801 0.4285 0.4633 0.146 Uiso 0.50 1 d P H 1 H22W H 1.1517 0.4968 0.4601 0.146 Uiso 0.50 1 d P I 1 O3W O 1.0544(8) 0.5758(4) 0.42473(18) 0.111(2) Uani 0.50 1 d P J 1 H31W H 0.9764 0.5369 0.4358 0.166 Uiso 0.50 1 d P K 1 H32W H 1.0350 0.6443 0.4310 0.166 Uiso 0.50 1 d P L 1 O21W O 1.0393(6) 0.4462(3) 0.49435(13) 0.0556(14) Uani 0.50 1 d P M 2 H23W H 0.9437 0.4358 0.4829 0.083 Uiso 0.50 1 d P N 2 H24W H 1.1005 0.4866 0.4786 0.083 Uiso 0.50 1 d P O 2 O31W O 1.1749(5) 0.5741(3) 0.43487(13) 0.0465(14) Uani 0.50 1 d P P 2 H33W H 1.2727 0.5421 0.4406 0.070 Uiso 0.50 1 d P Q 2 H34W H 1.1947 0.6441 0.4344 0.070 Uiso 0.50 1 d P R 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0769(15) 0.0196(8) 0.0328(12) 0.0087(7) -0.0171(11) -0.0029(9) O2 0.0722(15) 0.0214(8) 0.0203(11) 0.0022(7) 0.0032(11) -0.0027(10) O3 0.0687(13) 0.0172(7) 0.0255(11) 0.0007(7) 0.0011(11) -0.0072(10) O4 0.0754(14) 0.0234(8) 0.0224(11) -0.0055(7) -0.0013(11) 0.0092(10) N1 0.0425(14) 0.0145(8) 0.0181(13) 0.0010(9) -0.0036(12) 0.0052(10) N2 0.0822(19) 0.0258(11) 0.0156(14) 0.0077(10) -0.0014(14) -0.0025(13) C1 0.0470(18) 0.0190(10) 0.0131(15) -0.0020(10) -0.0017(16) 0.0020(12) C2 0.0431(19) 0.0291(12) 0.0200(16) 0.0055(11) 0.0053(16) 0.0044(13) C3 0.0433(18) 0.0136(10) 0.0252(16) -0.0013(10) 0.0042(16) 0.0029(13) C4 0.0391(18) 0.0199(11) 0.0195(16) -0.0057(10) 0.0013(15) 0.0016(12) C5 0.0345(17) 0.0203(11) 0.0121(15) 0.0039(10) -0.0037(14) 0.0019(12) C6 0.0347(17) 0.0198(11) 0.0202(16) 0.0014(11) -0.0010(14) 0.0038(12) C7 0.0456(18) 0.0183(11) 0.0102(15) -0.0028(11) -0.0042(14) 0.0041(13) C8 0.0517(19) 0.0189(11) 0.0206(18) -0.0009(11) -0.0045(16) -0.0060(13) C9 0.0398(18) 0.0209(11) 0.0352(19) -0.0079(12) -0.0071(16) 0.0035(14) C10 0.0416(18) 0.0191(10) 0.0300(17) -0.0009(11) -0.0088(16) 0.0056(14) C11 0.053(2) 0.0216(11) 0.0394(19) 0.0052(12) -0.0189(18) 0.0026(14) C12 0.105(3) 0.0206(12) 0.046(2) 0.0120(13) -0.024(2) 0.0029(18) C13 0.113(3) 0.0274(13) 0.030(2) 0.0082(13) -0.022(2) -0.0003(18) C14 0.087(2) 0.0283(13) 0.0236(17) 0.0079(12) -0.0177(19) -0.0005(17) C15 0.102(3) 0.0336(14) 0.024(2) 0.0103(13) -0.019(2) -0.0119(18) C16 0.065(2) 0.0290(13) 0.0236(19) -0.0046(12) 0.0007(17) -0.0056(15) C17 0.056(2) 0.0232(12) 0.0167(17) 0.0005(12) 0.0008(16) 0.0000(14) C18 0.0532(19) 0.0155(11) 0.0325(18) -0.0022(11) -0.0162(16) 0.0029(14) C19 0.070(2) 0.0208(12) 0.044(2) -0.0006(13) -0.0351(19) 0.0045(15) C20 0.065(2) 0.0266(13) 0.033(2) 0.0004(13) -0.0174(17) -0.0021(15) C21 0.053(2) 0.0187(11) 0.0240(17) 0.0025(11) -0.0118(17) 0.0019(13) C22 0.099(3) 0.0393(14) 0.0206(18) 0.0022(13) 0.010(2) -0.0057(18) C23 0.082(2) 0.0193(11) 0.0323(19) -0.0010(12) -0.0019(19) -0.0062(16) O5 0.118(4) 0.042(2) 0.031(3) -0.021(2) 0.013(3) -0.035(3) O6 0.136(4) 0.038(2) 0.039(3) -0.007(2) -0.015(3) 0.011(3) O7 0.083(3) 0.052(2) 0.068(3) 0.009(2) -0.029(3) -0.002(3) O8 0.035(2) 0.050(2) 0.043(3) -0.026(2) 0.015(2) -0.019(2) N3 0.109(3) 0.0349(19) 0.027(2) -0.0004(18) 0.009(2) -0.028(2) N4 0.088(4) 0.051(3) 0.058(4) -0.002(3) -0.009(3) -0.019(3) C24 0.116(3) 0.026(2) 0.026(3) 0.002(2) 0.003(3) -0.022(3) C25 0.107(3) 0.033(2) 0.024(2) -0.001(2) 0.005(2) -0.021(2) C26 0.100(3) 0.038(2) 0.023(3) 0.002(2) 0.006(3) -0.011(3) C27 0.091(4) 0.030(2) 0.027(3) 0.010(2) 0.000(3) -0.016(3) C28 0.075(3) 0.033(2) 0.022(3) -0.003(2) 0.005(3) -0.025(3) C29 0.035(2) 0.0210(19) 0.029(2) 0.0019(19) 0.009(2) -0.012(2) C30 0.024(3) 0.023(2) 0.041(3) 0.006(2) 0.011(3) -0.004(2) C31 0.021(3) 0.027(2) 0.039(3) 0.002(2) 0.008(2) -0.001(2) C32 0.017(3) 0.023(2) 0.040(3) 0.008(2) 0.016(2) 0.006(2) C33 0.015(2) 0.033(2) 0.041(3) 0.016(2) 0.006(2) 0.010(2) C34 0.019(3) 0.029(2) 0.030(3) 0.009(2) 0.006(2) 0.002(2) O5A 0.127(5) 0.057(3) 0.041(4) -0.004(3) 0.009(4) -0.034(4) O6A 0.128(5) 0.038(3) 0.034(3) -0.011(2) -0.009(4) 0.013(4) O7A 0.076(3) 0.034(2) 0.031(3) 0.008(2) 0.010(3) -0.001(2) O8A 0.036(3) 0.046(2) 0.037(3) -0.018(2) 0.008(2) -0.024(2) N3A 0.110(3) 0.036(2) 0.027(2) -0.001(2) 0.009(3) -0.028(2) N4A 0.079(4) 0.031(2) 0.037(4) 0.008(2) -0.009(3) -0.023(3) C24A 0.108(3) 0.018(2) 0.022(3) 0.002(2) 0.007(3) -0.017(3) C25A 0.106(3) 0.030(2) 0.022(2) -0.001(2) 0.007(2) -0.019(2) C26A 0.099(3) 0.040(3) 0.022(3) 0.007(2) 0.008(3) -0.016(3) C27A 0.088(3) 0.039(3) 0.020(3) 0.010(2) 0.007(3) -0.016(3) C28A 0.067(3) 0.024(2) 0.014(2) 0.003(2) 0.011(2) -0.020(2) C29A 0.034(3) 0.023(2) 0.028(3) 0.010(2) -0.001(3) -0.005(2) C30A 0.019(3) 0.021(2) 0.038(3) 0.009(2) 0.006(2) -0.006(2) C31A 0.015(3) 0.026(2) 0.045(3) 0.008(2) 0.001(3) -0.004(2) C32A 0.026(3) 0.043(2) 0.056(3) 0.031(2) -0.003(3) 0.000(2) C33A 0.022(3) 0.053(3) 0.048(3) 0.029(2) 0.007(3) 0.008(3) C34A 0.023(3) 0.038(2) 0.039(3) 0.016(2) 0.003(3) 0.004(2) O1W 0.0832(18) 0.0669(13) 0.0750(18) -0.0035(14) 0.0062(16) -0.0301(14) O2W 0.158(5) 0.068(3) 0.066(4) 0.020(2) -0.049(4) -0.005(4) O3W 0.123(6) 0.090(4) 0.120(5) 0.012(3) -0.004(4) 0.015(4) O21W 0.068(3) 0.051(2) 0.047(3) 0.013(2) 0.004(3) -0.006(3) O31W 0.044(3) 0.040(2) 0.056(3) 0.0138(19) -0.019(3) 0.000(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C11 1.430(3) . ? O1 C12 1.443(3) . ? O2 C2 1.368(3) . ? O2 C22 1.438(3) . ? O3 C3 1.382(2) . ? O3 C23 1.447(2) . ? O4 C9 1.221(3) . ? N1 C9 1.368(3) . ? N1 C6 1.426(3) . ? N1 C8 1.503(3) . ? N2 C15 1.506(3) . ? N2 C16 1.514(4) . ? N2 C21 1.520(3) . ? N2 H2 0.9300 . ? C1 C6 1.377(3) . ? C1 C2 1.393(3) . ? C1 H1 0.9500 . ? C2 C3 1.411(3) . ? C3 C4 1.378(3) . ? C4 C5 1.395(3) . ? C4 H4 0.9500 . ? C5 C6 1.388(3) . ? C5 C7 1.520(3) . ? C7 C21 1.521(3) . ? C7 C17 1.546(4) . ? C7 C8 1.564(3) . ? C8 C18 1.514(4) . ? C8 H8 1.0000 . ? C9 C10 1.532(3) . ? C10 C11 1.546(3) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C18 1.553(3) . ? C11 H11 1.0000 . ? C12 C13 1.500(4) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.317(3) . ? C13 H13 0.9500 . ? C14 C19 1.506(4) . ? C14 C15 1.509(4) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 C17 1.508(3) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 C19 1.534(4) . ? C18 H18 1.0000 . ? C19 C20 1.548(3) . ? C19 H19 1.0000 . ? C20 C21 1.509(4) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C21 H21 1.0000 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? O5 C24 1.411(9) . ? O6 C24 1.064(9) . ? O7 C27 1.227(8) . ? O8 C28 1.210(7) . ? N3 C25 1.312(8) . ? N3 C28 1.461(6) . ? N3 H37 0.9809 . ? N4 C27 1.318(8) . ? N4 H47A 0.8800 . ? N4 H47B 0.8800 . ? C24 C25 1.625(10) . ? C25 C26 1.465(9) . ? C25 H25 1.1751 . ? C26 C27 1.522(8) . ? C26 H26A 0.9900 . ? C26 H26B 0.9900 . ? C26 H26C 1.2264 . ? C26 H26D 1.5425 . ? C28 C29 1.566(9) . ? C29 C34 1.355(8) . ? C29 C30 1.398(7) . ? C30 C31 1.421(7) . ? C30 H30 0.9500 . ? C31 C32 1.419(7) . ? C31 H31 0.9500 . ? C32 C33 1.430(7) . ? C32 H32 0.9500 . ? C33 C34 1.420(7) . ? C33 H33 0.9500 . ? C34 H34 0.9500 . ? O5A C24A 1.201(10) . ? O6A C24A 1.374(10) . ? O7A C27A 1.245(8) . ? O8A C28A 1.206(7) . ? N3A C28A 1.321(7) . ? N3A C25A 1.640(10) . ? N3A H37 0.9292 . ? N3A H37A 0.8800 . ? N4A C27A 1.355(8) . ? N4A H47C 0.8800 . ? N4A H47D 0.8800 . ? C24A C25A 1.462(10) . ? C25A C26A 1.627(10) . ? C25A H25 0.8630 . ? C25A H25A 1.0000 . ? C26A C27A 1.494(9) . ? C26A H26C 0.9573 . ? C26A H26D 0.9926 . ? C28A C29A 1.493(9) . ? C29A C34A 1.373(8) . ? C29A C30A 1.424(8) . ? C30A C31A 1.368(8) . ? C30A H30A 0.9500 . ? C31A C32A 1.434(8) . ? C31A H31A 0.9500 . ? C32A C33A 1.382(8) . ? C32A H32A 0.9500 . ? C33A C34A 1.371(8) . ? C33A H33A 0.9500 . ? C34A H34A 0.9500 . ? O1W H11W 0.8630 . ? O1W H12W 0.8549 . ? O2W H21W 0.8904 . ? O2W H22W 0.8916 . ? O2W H24W 0.8611 . ? O3W H31W 0.8634 . ? O3W H32W 0.8924 . ? O3W H34W 1.4306 . ? O21W H23W 0.8532 . ? O21W H24W 0.8690 . ? O31W H22W 1.2869 . ? O31W H32W 1.4124 . ? O31W H33W 0.8875 . ? O31W H34W 0.8872 . ? 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 C11 O1 C12 114.7(2) . . ? C2 O2 C22 115.37(17) . . ? C3 O3 C23 116.25(16) . . ? C9 N1 C6 123.8(2) . . ? C9 N1 C8 119.86(18) . . ? C6 N1 C8 109.52(17) . . ? C15 N2 C16 113.4(2) . . ? C15 N2 C21 113.8(2) . . ? C16 N2 C21 107.90(19) . . ? C15 N2 H2 107.1 . . ? C16 N2 H2 107.1 . . ? C21 N2 H2 107.1 . . ? C6 C1 C2 118.1(2) . . ? C6 C1 H1 120.9 . . ? C2 C1 H1 120.9 . . ? O2 C2 C1 124.0(2) . . ? O2 C2 C3 115.73(18) . . ? C1 C2 C3 120.3(2) . . ? C4 C3 O3 124.8(2) . . ? C4 C3 C2 120.30(19) . . ? O3 C3 C2 114.9(2) . . ? C3 C4 C5 119.4(2) . . ? C3 C4 H4 120.3 . . ? C5 C4 H4 120.3 . . ? C6 C5 C4 119.4(2) . . ? C6 C5 C7 110.71(18) . . ? C4 C5 C7 129.8(2) . . ? C1 C6 C5 122.2(2) . . ? C1 C6 N1 128.0(2) . . ? C5 C6 N1 109.7(2) . . ? C5 C7 C21 116.9(2) . . ? C5 C7 C17 111.49(19) . . ? C21 C7 C17 101.6(2) . . ? C5 C7 C8 102.24(19) . . ? C21 C7 C8 114.54(19) . . ? C17 C7 C8 110.3(2) . . ? N1 C8 C18 107.0(2) . . ? N1 C8 C7 103.96(17) . . ? C18 C8 C7 116.2(2) . . ? N1 C8 H8 109.8 . . ? C18 C8 H8 109.8 . . ? C7 C8 H8 109.8 . . ? O4 C9 N1 123.0(2) . . ? O4 C9 C10 121.6(2) . . ? N1 C9 C10 115.4(2) . . ? C9 C10 C11 118.31(18) . . ? C9 C10 H10A 107.7 . . ? C11 C10 H10A 107.7 . . ? C9 C10 H10B 107.7 . . ? C11 C10 H10B 107.7 . . ? H10A C10 H10B 107.1 . . ? O1 C11 C10 104.4(2) . . ? O1 C11 C18 113.6(2) . . ? C10 C11 C18 110.33(18) . . ? O1 C11 H11 109.4 . . ? C10 C11 H11 109.4 . . ? C18 C11 H11 109.4 . . ? O1 C12 C13 111.3(2) . . ? O1 C12 H12A 109.4 . . ? C13 C12 H12A 109.4 . . ? O1 C12 H12B 109.4 . . ? C13 C12 H12B 109.4 . . ? H12A C12 H12B 108.0 . . ? C14 C13 C12 122.8(3) . . ? C14 C13 H13 118.6 . . ? C12 C13 H13 118.6 . . ? C13 C14 C19 122.9(3) . . ? C13 C14 C15 121.3(3) . . ? C19 C14 C15 115.8(2) . . ? N2 C15 C14 109.8(2) . . ? N2 C15 H15A 109.7 . . ? C14 C15 H15A 109.7 . . ? N2 C15 H15B 109.7 . . ? C14 C15 H15B 109.7 . . ? H15A C15 H15B 108.2 . . ? C17 C16 N2 103.8(2) . . ? C17 C16 H16A 111.0 . . ? N2 C16 H16A 111.0 . . ? C17 C16 H16B 111.0 . . ? N2 C16 H16B 111.0 . . ? H16A C16 H16B 109.0 . . ? C16 C17 C7 103.1(2) . . ? C16 C17 H17A 111.1 . . ? C7 C17 H17A 111.1 . . ? C16 C17 H17B 111.1 . . ? C7 C17 H17B 111.1 . . ? H17A C17 H17B 109.1 . . ? C8 C18 C19 111.9(2) . . ? C8 C18 C11 107.3(2) . . ? C19 C18 C11 117.45(19) . . ? C8 C18 H18 106.5 . . ? C19 C18 H18 106.5 . . ? C11 C18 H18 106.5 . . ? C14 C19 C18 115.3(2) . . ? C14 C19 C20 109.1(2) . . ? C18 C19 C20 106.2(2) . . ? C14 C19 H19 108.7 . . ? C18 C19 H19 108.7 . . ? C20 C19 H19 108.7 . . ? C21 C20 C19 108.4(2) . . ? C21 C20 H20A 110.0 . . ? C19 C20 H20A 110.0 . . ? C21 C20 H20B 110.0 . . ? C19 C20 H20B 110.0 . . ? H20A C20 H20B 108.4 . . ? C20 C21 N2 110.6(2) . . ? C20 C21 C7 115.1(2) . . ? N2 C21 C7 104.8(2) . . ? C20 C21 H21 108.7 . . ? N2 C21 H21 108.7 . . ? C7 C21 H21 108.7 . . ? O2 C22 H22A 109.5 . . ? O2 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? O2 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? O3 C23 H23A 109.5 . . ? O3 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? O3 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C25 N3 C28 110.8(4) . . ? C25 N3 H37 117.5 . . ? C28 N3 H37 129.6 . . ? C27 N4 H47A 120.0 . . ? C27 N4 H47B 120.0 . . ? H47A N4 H47B 120.0 . . ? O6 C24 O5 130.4(6) . . ? O6 C24 C25 121.9(7) . . ? O5 C24 C25 107.2(6) . . ? N3 C25 C26 115.2(5) . . ? N3 C25 C24 111.4(6) . . ? C26 C25 C24 110.6(5) . . ? N3 C25 H25 99.4 . . ? C26 C25 H25 101.8 . . ? C24 C25 H25 117.9 . . ? C25 C26 C27 113.7(6) . . ? C25 C26 H26A 108.8 . . ? C27 C26 H26A 108.8 . . ? C25 C26 H26B 108.8 . . ? C27 C26 H26B 108.8 . . ? H26A C26 H26B 107.7 . . ? C25 C26 H26C 105.4 . . ? C27 C26 H26C 134.7 . . ? H26A C26 H26C 77.8 . . ? H26B C26 H26C 33.6 . . ? C25 C26 H26D 96.3 . . ? C27 C26 H26D 124.9 . . ? H26A C26 H26D 16.6 . . ? H26B C26 H26D 102.9 . . ? H26C C26 H26D 70.0 . . ? O7 C27 N4 119.1(5) . . ? O7 C27 C26 124.1(5) . . ? N4 C27 C26 116.8(6) . . ? O8 C28 N3 133.4(5) . . ? O8 C28 C29 120.3(5) . . ? N3 C28 C29 106.2(5) . . ? C34 C29 C30 123.9(5) . . ? C34 C29 C28 121.5(5) . . ? C30 C29 C28 114.5(5) . . ? C29 C30 C31 117.5(5) . . ? C29 C30 H30 121.3 . . ? C31 C30 H30 121.3 . . ? C32 C31 C30 122.6(5) . . ? C32 C31 H31 118.7 . . ? C30 C31 H31 118.7 . . ? C31 C32 C33 115.2(5) . . ? C31 C32 H32 122.4 . . ? C33 C32 H32 122.4 . . ? C34 C33 C32 123.1(5) . . ? C34 C33 H33 118.4 . . ? C32 C33 H33 118.4 . . ? C29 C34 C33 117.7(5) . . ? C29 C34 H34 121.2 . . ? C33 C34 H34 121.2 . . ? C28A N3A C25A 126.4(6) . . ? C28A N3A H37 109.3 . . ? C25A N3A H37 120.6 . . ? C28A N3A H37A 116.8 . . ? C25A N3A H37A 116.8 . . ? H37 N3A H37A 21.4 . . ? C27A N4A H47C 120.0 . . ? C27A N4A H47D 120.0 . . ? H47C N4A H47D 120.0 . . ? O5A C24A O6A 117.8(7) . . ? O5A C24A C25A 122.9(8) . . ? O6A C24A C25A 119.3(7) . . ? C24A C25A C26A 107.9(5) . . ? C24A C25A N3A 109.2(6) . . ? C26A C25A N3A 111.5(5) . . ? C24A C25A H25 139.1 . . ? C26A C25A H25 89.1 . . ? N3A C25A H25 97.8 . . ? C24A C25A H25A 109.4 . . ? C26A C25A H25A 109.4 . . ? N3A C25A H25A 109.4 . . ? H25 C25A H25A 30.5 . . ? C27A C26A C25A 109.6(6) . . ? C27A C26A H26C 110.3 . . ? C25A C26A H26C 113.1 . . ? C27A C26A H26D 108.6 . . ? C25A C26A H26D 103.8 . . ? H26C C26A H26D 111.3 . . ? O7A C27A N4A 119.2(6) . . ? O7A C27A C26A 124.0(6) . . ? N4A C27A C26A 116.8(6) . . ? O8A C28A N3A 111.8(6) . . ? O8A C28A C29A 122.7(5) . . ? N3A C28A C29A 125.5(6) . . ? C34A C29A C30A 120.3(6) . . ? C34A C29A C28A 126.1(6) . . ? C30A C29A C28A 113.4(5) . . ? C31A C30A C29A 118.0(6) . . ? C31A C30A H30A 121.0 . . ? C29A C30A H30A 121.0 . . ? C30A C31A C32A 120.9(6) . . ? C30A C31A H31A 119.5 . . ? C32A C31A H31A 119.5 . . ? C33A C32A C31A 119.6(6) . . ? C33A C32A H32A 120.2 . . ? C31A C32A H32A 120.2 . . ? C34A C33A C32A 119.1(6) . . ? C34A C33A H33A 120.5 . . ? C32A C33A H33A 120.5 . . ? C33A C34A C29A 122.1(6) . . ? C33A C34A H34A 119.0 . . ? C29A C34A H34A 119.0 . . ? H11W O1W H12W 108.5 . . ? H21W O2W H22W 96.1 . . ? H21W O2W H24W 144.2 . . ? H22W O2W H24W 50.2 . . ? H31W O3W H32W 108.5 . . ? H31W O3W H34W 142.1 . . ? H32W O3W H34W 60.6 . . ? H23W O21W H24W 108.2 . . ? H22W O31W H32W 114.3 . . ? H22W O31W H33W 69.4 . . ? H32W O31W H33W 166.9 . . ? H22W O31W H34W 140.7 . . ? H32W O31W H34W 61.6 . . ? H33W O31W H34W 107.1 . . ? 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 C22 O2 C2 C1 0.6(4) . . . . ? C22 O2 C2 C3 -178.5(3) . . . . ? C6 C1 C2 O2 -178.2(2) . . . . ? C6 C1 C2 C3 0.8(4) . . . . ? C23 O3 C3 C4 1.0(4) . . . . ? C23 O3 C3 C2 -180.0(2) . . . . ? O2 C2 C3 C4 175.4(2) . . . . ? C1 C2 C3 C4 -3.7(4) . . . . ? O2 C2 C3 O3 -3.7(4) . . . . ? C1 C2 C3 O3 177.2(2) . . . . ? O3 C3 C4 C5 -178.4(2) . . . . ? C2 C3 C4 C5 2.6(4) . . . . ? C3 C4 C5 C6 1.2(4) . . . . ? C3 C4 C5 C7 -174.9(3) . . . . ? C2 C1 C6 C5 3.1(4) . . . . ? C2 C1 C6 N1 -175.3(2) . . . . ? C4 C5 C6 C1 -4.2(4) . . . . ? C7 C5 C6 C1 172.6(2) . . . . ? C4 C5 C6 N1 174.5(2) . . . . ? C7 C5 C6 N1 -8.7(3) . . . . ? C9 N1 C6 C1 23.2(4) . . . . ? C8 N1 C6 C1 173.9(3) . . . . ? C9 N1 C6 C5 -155.4(2) . . . . ? C8 N1 C6 C5 -4.6(3) . . . . ? C6 C5 C7 C21 143.5(2) . . . . ? C4 C5 C7 C21 -40.2(4) . . . . ? C6 C5 C7 C17 -100.3(2) . . . . ? C4 C5 C7 C17 76.1(3) . . . . ? C6 C5 C7 C8 17.6(3) . . . . ? C4 C5 C7 C8 -166.1(3) . . . . ? C9 N1 C8 C18 43.8(3) . . . . ? C6 N1 C8 C18 -108.2(2) . . . . ? C9 N1 C8 C7 167.3(2) . . . . ? C6 N1 C8 C7 15.3(3) . . . . ? C5 C7 C8 N1 -19.0(2) . . . . ? C21 C7 C8 N1 -146.4(2) . . . . ? C17 C7 C8 N1 99.7(2) . . . . ? C5 C7 C8 C18 98.3(2) . . . . ? C21 C7 C8 C18 -29.1(3) . . . . ? C17 C7 C8 C18 -143.0(2) . . . . ? C6 N1 C9 O4 -26.1(4) . . . . ? C8 N1 C9 O4 -174.0(2) . . . . ? C6 N1 C9 C10 155.7(2) . . . . ? C8 N1 C9 C10 7.8(3) . . . . ? O4 C9 C10 C11 148.5(3) . . . . ? N1 C9 C10 C11 -33.2(4) . . . . ? C12 O1 C11 C10 170.21(19) . . . . ? C12 O1 C11 C18 -69.5(3) . . . . ? C9 C10 C11 O1 126.8(2) . . . . ? C9 C10 C11 C18 4.4(3) . . . . ? C11 O1 C12 C13 88.9(3) . . . . ? O1 C12 C13 C14 -61.6(4) . . . . ? C12 C13 C14 C19 -5.8(5) . . . . ? C12 C13 C14 C15 174.8(3) . . . . ? C16 N2 C15 C14 77.3(3) . . . . ? C21 N2 C15 C14 -46.5(3) . . . . ? C13 C14 C15 N2 -128.2(3) . . . . ? C19 C14 C15 N2 52.3(3) . . . . ? C15 N2 C16 C17 -143.0(2) . . . . ? C21 N2 C16 C17 -15.9(2) . . . . ? N2 C16 C17 C7 36.6(2) . . . . ? C5 C7 C17 C16 -168.77(19) . . . . ? C21 C7 C17 C16 -43.5(2) . . . . ? C8 C7 C17 C16 78.4(2) . . . . ? N1 C8 C18 C19 159.16(18) . . . . ? C7 C8 C18 C19 43.6(3) . . . . ? N1 C8 C18 C11 -70.7(2) . . . . ? C7 C8 C18 C11 173.7(2) . . . . ? O1 C11 C18 C8 -71.0(3) . . . . ? C10 C11 C18 C8 45.9(3) . . . . ? O1 C11 C18 C19 55.9(3) . . . . ? C10 C11 C18 C19 172.8(2) . . . . ? C13 C14 C19 C18 60.5(4) . . . . ? C15 C14 C19 C18 -120.0(3) . . . . ? C13 C14 C19 C20 179.8(3) . . . . ? C15 C14 C19 C20 -0.7(3) . . . . ? C8 C18 C19 C14 58.5(3) . . . . ? C11 C18 C19 C14 -66.2(3) . . . . ? C8 C18 C19 C20 -62.4(3) . . . . ? C11 C18 C19 C20 172.9(2) . . . . ? C14 C19 C20 C21 -56.4(3) . . . . ? C18 C19 C20 C21 68.5(3) . . . . ? C19 C20 C21 N2 62.0(3) . . . . ? C19 C20 C21 C7 -56.5(3) . . . . ? C15 N2 C21 C20 -9.2(3) . . . . ? C16 N2 C21 C20 -135.9(2) . . . . ? C15 N2 C21 C7 115.5(2) . . . . ? C16 N2 C21 C7 -11.3(2) . . . . ? C5 C7 C21 C20 -83.5(3) . . . . ? C17 C7 C21 C20 154.9(2) . . . . ? C8 C7 C21 C20 36.0(3) . . . . ? C5 C7 C21 N2 154.73(19) . . . . ? C17 C7 C21 N2 33.2(2) . . . . ? C8 C7 C21 N2 -85.8(2) . . . . ? C28 N3 C25 C26 -84.6(6) . . . . ? C28 N3 C25 C24 148.3(4) . . . . ? O6 C24 C25 N3 26.2(8) . . . . ? O5 C24 C25 N3 -160.7(4) . . . . ? O6 C24 C25 C26 -103.4(8) . . . . ? O5 C24 C25 C26 69.8(6) . . . . ? N3 C25 C26 C27 -76.5(7) . . . . ? C24 C25 C26 C27 51.0(8) . . . . ? C25 C26 C27 O7 67.3(8) . . . . ? C25 C26 C27 N4 -114.2(7) . . . . ? C25 N3 C28 O8 2.5(8) . . . . ? C25 N3 C28 C29 178.4(4) . . . . ? O8 C28 C29 C34 -157.1(5) . . . . ? N3 C28 C29 C34 26.4(6) . . . . ? O8 C28 C29 C30 19.5(7) . . . . ? N3 C28 C29 C30 -157.1(4) . . . . ? C34 C29 C30 C31 -2.4(8) . . . . ? C28 C29 C30 C31 -178.8(4) . . . . ? C29 C30 C31 C32 1.7(7) . . . . ? C30 C31 C32 C33 -1.1(7) . . . . ? C31 C32 C33 C34 1.1(7) . . . . ? C30 C29 C34 C33 2.4(8) . . . . ? C28 C29 C34 C33 178.6(4) . . . . ? C32 C33 C34 C29 -1.7(8) . . . . ? O5A C24A C25A C26A 65.8(9) . . . . ? O6A C24A C25A C26A -114.6(7) . . . . ? O5A C24A C25A N3A -172.9(6) . . . . ? O6A C24A C25A N3A 6.7(8) . . . . ? C28A N3A C25A C24A 156.0(5) . . . . ? C28A N3A C25A C26A -84.8(7) . . . . ? C24A C25A C26A C27A 48.8(8) . . . . ? N3A C25A C26A C27A -71.1(7) . . . . ? C25A C26A C27A O7A 78.2(8) . . . . ? C25A C26A C27A N4A -100.9(7) . . . . ? C25A N3A C28A O8A 7.3(8) . . . . ? C25A N3A C28A C29A -171.1(5) . . . . ? O8A C28A C29A C34A -154.6(6) . . . . ? N3A C28A C29A C34A 23.7(9) . . . . ? O8A C28A C29A C30A 19.9(8) . . . . ? N3A C28A C29A C30A -161.9(5) . . . . ? C34A C29A C30A C31A 1.8(8) . . . . ? C28A C29A C30A C31A -173.0(5) . . . . ? C29A C30A C31A C32A -2.5(8) . . . . ? C30A C31A C32A C33A 2.9(8) . . . . ? C31A C32A C33A C34A -2.4(8) . . . . ? C32A C33A C34A C29A 1.7(9) . . . . ? C30A C29A C34A C33A -1.4(9) . . . . ? C28A C29A C34A C33A 172.7(5) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2 O5A 0.93 1.67 2.588(5) 169.1 . N2 H2 O5 0.93 1.75 2.671(3) 168.7 . N2 H2 O6A 0.93 2.50 3.143(5) 126.4 . N2 H2 O6 0.93 2.51 3.139(3) 125.2 . N4 H47A O2W 0.88 2.02 2.899(7) 175.6 4_456 N3A H37A O21W 0.88 2.03 2.902(7) 173.3 . N4A H47C O21W 0.88 2.09 2.941(6) 161.4 4_456 O1W H11W O4 0.86 1.97 2.829(3) 176.6 3_755 O1W H12W O3W 0.85 1.74 2.508(6) 148.8 . O1W H12W O31W 0.85 2.20 3.036(5) 166.5 . O2W H21W O5 0.89 1.82 2.562(6) 139.3 1_655 O2W H22W O3W 0.89 1.71 2.600(7) 177.0 . O3W H31W O6 0.86 1.97 2.827(7) 171.1 . O3W H32W O8 0.89 1.93 2.787(6) 159.7 4_566 O21W H23W O6A 0.85 1.68 2.495(7) 160.1 . O21W H24W O31W 0.87 1.90 2.746(6) 163.0 . O31W H33W O5A 0.89 1.99 2.869(7) 170.3 1_655 O31W H34W O8A 0.89 1.93 2.780(5) 161.0 4_566 _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 28.00 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.173 _refine_diff_density_min -0.194 _refine_diff_density_rms 0.040 # Attachment 'cif 3.txt' data_3 _database_code_depnum_ccdc_archive 'CCDC 288084' _audit_creation_method SHELXL-97 _chemical_name_systematic ; brucinium N-tert-Butoxycarbonyl-L-alaninate 2-propanol solvate hydrate ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C23 H27 N2 O4, C8 H14 N O4, C3 H8 O, H2 O' _chemical_formula_sum 'C34 H51 N3 O10' _chemical_formula_weight 661.78 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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting MONOCLINIC _symmetry_space_group_name_H-M 'C 2' _symmetry_space_group_name_Hall 'C 2y' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' _cell_length_a 13.611(2) _cell_length_b 12.374(2) _cell_length_c 20.458(3) _cell_angle_alpha 90.00 _cell_angle_beta 93.146(18) _cell_angle_gamma 90.00 _cell_volume 3440.2(10) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 1896 _cell_measurement_theta_min 3.44 _cell_measurement_theta_max 25.00 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.278 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1424 _exptl_absorpt_coefficient_mu 0.094 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 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 'Kuma KM4CCD' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9880 _diffrn_reflns_av_R_equivalents 0.0465 _diffrn_reflns_av_sigmaI/netI 0.0586 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 3.44 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3132 _reflns_number_gt 2644 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD (Oxford Diffraction,Poland Sp. z o.o)' _computing_cell_refinement 'CrysAlis RED (Oxford Diffraction,Poland Sp. z o.o)' _computing_data_reduction 'CrysAlis RED (Oxford Diffraction,Poland Sp. z o.o)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL-NT V5.1, Bruker AXS 1999' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0335P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _chemical_absolute_configuration rm _refine_ls_abs_structure_details 'from known structure (Toda et al., 1985)' _refine_ls_number_reflns 3132 _refine_ls_number_parameters 424 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0555 _refine_ls_R_factor_gt 0.0406 _refine_ls_wR_factor_ref 0.0735 _refine_ls_wR_factor_gt 0.0687 _refine_ls_goodness_of_fit_ref 1.000 _refine_ls_restrained_S_all 1.000 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.82936(16) 0.01201(16) 0.14091(10) 0.0210(5) Uani 1 1 d . . . O2 O 0.91420(15) 0.60141(16) -0.08459(10) 0.0190(5) Uani 1 1 d . . . O3 O 0.88075(16) 0.71500(15) 0.01815(10) 0.0195(5) Uani 1 1 d . . . O4 O 0.90475(15) 0.19790(17) -0.05059(10) 0.0201(5) Uani 1 1 d . . . N1 N 0.83094(18) 0.27102(19) 0.03724(11) 0.0155(6) Uani 1 1 d . . . N2 N 0.71482(19) 0.3492(2) 0.23896(12) 0.0200(6) Uani 1 1 d . . . H2 H 0.6939 0.4045 0.2657 0.024 Uiso 1 1 calc R . . C1 C 0.8744(2) 0.4330(2) -0.03168(15) 0.0165(7) Uani 1 1 d . . . H1 H 0.8895 0.3912 -0.0688 0.020 Uiso 1 1 calc R . . C2 C 0.8844(2) 0.5436(3) -0.03161(14) 0.0161(7) Uani 1 1 d . . . C3 C 0.8635(2) 0.6064(2) 0.02363(14) 0.0165(7) Uani 1 1 d . . . C4 C 0.8266(2) 0.5561(2) 0.07835(15) 0.0165(7) Uani 1 1 d . . . H4 H 0.8089 0.5977 0.1149 0.020 Uiso 1 1 calc R . . C5 C 0.8163(2) 0.4435(2) 0.07846(14) 0.0157(7) Uani 1 1 d . . . C6 C 0.8415(2) 0.3842(2) 0.02465(15) 0.0144(7) Uani 1 1 d . . . C7 C 0.7713(2) 0.3707(2) 0.12873(15) 0.0163(7) Uani 1 1 d . . . C8 C 0.8024(2) 0.2553(2) 0.10571(14) 0.0138(7) Uani 1 1 d . . . H8 H 0.7447 0.2054 0.1061 0.017 Uiso 1 1 calc R . . C9 C 0.8741(2) 0.1886(2) 0.00534(15) 0.0167(7) Uani 1 1 d . . . C10 C 0.8796(2) 0.0823(2) 0.04170(15) 0.0184(7) Uani 1 1 d . . . H10A H 0.9320 0.0382 0.0232 0.022 Uiso 1 1 calc R . . H10B H 0.8166 0.0437 0.0326 0.022 Uiso 1 1 calc R . . C11 C 0.8996(2) 0.0868(2) 0.11665(15) 0.0181(7) Uani 1 1 d . . . H11 H 0.9676 0.0593 0.1279 0.022 Uiso 1 1 calc R . . C12 C 0.8394(3) -0.0112(3) 0.20981(15) 0.0229(8) Uani 1 1 d . . . H12A H 0.9097 -0.0075 0.2249 0.027 Uiso 1 1 calc R . . H12B H 0.8156 -0.0854 0.2179 0.027 Uiso 1 1 calc R . . C13 C 0.7812(2) 0.0683(2) 0.24794(15) 0.0207(8) Uani 1 1 d . . . H13 H 0.7279 0.0433 0.2719 0.025 Uiso 1 1 calc R . . C14 C 0.8035(2) 0.1739(2) 0.24864(14) 0.0181(7) Uani 1 1 d . . . C15 C 0.7415(2) 0.2539(2) 0.28282(15) 0.0224(8) Uani 1 1 d . . . H15A H 0.7781 0.2799 0.3230 0.027 Uiso 1 1 calc R . . H15B H 0.6806 0.2181 0.2960 0.027 Uiso 1 1 calc R . . C16 C 0.6314(2) 0.3249(3) 0.18961(16) 0.0228(8) Uani 1 1 d . . . H16A H 0.5684 0.3528 0.2048 0.027 Uiso 1 1 calc R . . H16B H 0.6251 0.2461 0.1823 0.027 Uiso 1 1 calc R . . C17 C 0.6582(2) 0.3820(2) 0.12735(15) 0.0177(7) Uani 1 1 d . . . H17A H 0.6382 0.4589 0.1278 0.021 Uiso 1 1 calc R . . H17B H 0.6268 0.3466 0.0882 0.021 Uiso 1 1 calc R . . C18 C 0.8911(2) 0.2029(2) 0.14217(14) 0.0155(7) Uani 1 1 d . . . H18 H 0.9501 0.2420 0.1272 0.019 Uiso 1 1 calc R . . C19 C 0.8922(2) 0.2199(2) 0.21653(15) 0.0182(7) Uani 1 1 d . . . H19 H 0.9531 0.1860 0.2371 0.022 Uiso 1 1 calc R . . C20 C 0.8970(2) 0.3434(2) 0.22798(16) 0.0199(7) Uani 1 1 d . . . H20A H 0.9074 0.3589 0.2753 0.024 Uiso 1 1 calc R . . H20B H 0.9527 0.3747 0.2051 0.024 Uiso 1 1 calc R . . C21 C 0.8003(2) 0.3934(3) 0.20157(14) 0.0183(7) Uani 1 1 d . . . H21 H 0.8039 0.4734 0.2082 0.022 Uiso 1 1 calc R . . C22 C 0.9367(2) 0.5371(3) -0.14067(15) 0.0202(8) Uani 1 1 d . . . H22A H 0.9570 0.5846 -0.1758 0.030 Uiso 1 1 calc R . . H22B H 0.8781 0.4963 -0.1559 0.030 Uiso 1 1 calc R . . H22C H 0.9901 0.4868 -0.1284 0.030 Uiso 1 1 calc R . . C23 C 0.8756(3) 0.7782(3) 0.07620(16) 0.0269(8) Uani 1 1 d . . . H23A H 0.8890 0.8541 0.0662 0.040 Uiso 1 1 calc R . . H23B H 0.9245 0.7521 0.1094 0.040 Uiso 1 1 calc R . . H23C H 0.8096 0.7720 0.0928 0.040 Uiso 1 1 calc R . . O5 O 0.66942(19) 0.47868(17) 0.33168(11) 0.0351(7) Uani 1 1 d . . . O6 O 0.61836(18) 0.59466(18) 0.25395(10) 0.0312(6) Uani 1 1 d . . . O7 O 0.62717(18) 0.94017(18) 0.36105(12) 0.0344(6) Uani 1 1 d . . . O8 O 0.68054(18) 0.81571(18) 0.43714(11) 0.0312(6) Uani 1 1 d . . . N3 N 0.6082(2) 0.7594(2) 0.34403(13) 0.0253(7) Uani 1 1 d . . . H3 H 0.5844 0.7706 0.3038 0.030 Uiso 1 1 calc R . . C24 C 0.6360(2) 0.5687(3) 0.31189(16) 0.0204(8) Uani 1 1 d . . . C25 C 0.6134(3) 0.6468(3) 0.36731(16) 0.0235(8) Uani 1 1 d . . . H25 H 0.6677 0.6414 0.4021 0.028 Uiso 1 1 calc R . . C26 C 0.5174(3) 0.6134(3) 0.39693(17) 0.0345(9) Uani 1 1 d . . . H26A H 0.5030 0.6632 0.4324 0.052 Uiso 1 1 calc R . . H26B H 0.5239 0.5398 0.4143 0.052 Uiso 1 1 calc R . . H26C H 0.4637 0.6157 0.3631 0.052 Uiso 1 1 calc R . . C27 C 0.6373(2) 0.8466(3) 0.37968(17) 0.0256(8) Uani 1 1 d . . . C28 C 0.7254(3) 0.8941(3) 0.48478(17) 0.0318(9) Uani 1 1 d . . . C29 C 0.6460(3) 0.9609(4) 0.5137(2) 0.0598(14) Uani 1 1 d . . . H29A H 0.6157 1.0082 0.4799 0.090 Uiso 1 1 calc R . . H29B H 0.6748 1.0049 0.5497 0.090 Uiso 1 1 calc R . . H29C H 0.5958 0.9129 0.5304 0.090 Uiso 1 1 calc R . . C30 C 0.8017(3) 0.9623(3) 0.4530(2) 0.0459(11) Uani 1 1 d . . . H30A H 0.7691 1.0101 0.4204 0.069 Uiso 1 1 calc R . . H30B H 0.8481 0.9151 0.4316 0.069 Uiso 1 1 calc R . . H30C H 0.8375 1.0059 0.4865 0.069 Uiso 1 1 calc R . . C31 C 0.7744(3) 0.8188(3) 0.53567(18) 0.0497(12) Uani 1 1 d . . . H31A H 0.7242 0.7748 0.5555 0.075 Uiso 1 1 calc R . . H31B H 0.8098 0.8617 0.5697 0.075 Uiso 1 1 calc R . . H31C H 0.8209 0.7715 0.5145 0.075 Uiso 1 1 calc R . . O33 O 0.51618(19) 1.1013(2) 0.29307(11) 0.0447(7) Uani 1 1 d . . . H33 H 0.5395 1.0553 0.3113 0.067 Uiso 1 1 d R . . C34 C 0.3775(3) 1.2142(4) 0.2873(2) 0.0537(12) Uani 1 1 d . . . H34A H 0.3558 1.1788 0.2462 0.081 Uiso 1 1 calc R . . H34B H 0.4185 1.2768 0.2780 0.081 Uiso 1 1 calc R . . H34C H 0.3199 1.2382 0.3102 0.081 Uiso 1 1 calc R . . C32 C 0.4720(4) 1.1850(4) 0.3934(2) 0.0656(14) Uani 1 1 d . . . H32A H 0.5099 1.1312 0.4193 0.098 Uiso 1 1 calc R . . H32B H 0.4156 1.2087 0.4176 0.098 Uiso 1 1 calc R . . H32C H 0.5140 1.2472 0.3850 0.098 Uiso 1 1 calc R . . C33 C 0.4360(3) 1.1359(3) 0.32982(17) 0.0326(9) Uani 1 1 d . . . H33A H 0.3938 1.0721 0.3388 0.039 Uiso 1 1 calc R . . O1W O 0.65292(18) 0.77415(19) 0.17807(11) 0.0381(7) Uani 1 1 d . . . H11W H 0.6403 0.7492 0.1322 0.057 Uiso 1 1 d R . . H12W H 0.6438 0.7221 0.2029 0.057 Uiso 1 1 d R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0259(13) 0.0180(12) 0.0195(12) 0.0020(10) 0.0052(10) -0.0038(10) O2 0.0237(13) 0.0154(11) 0.0184(12) 0.0031(10) 0.0050(10) 0.0036(10) O3 0.0265(13) 0.0120(11) 0.0201(13) -0.0005(10) 0.0012(10) -0.0001(10) O4 0.0235(13) 0.0214(12) 0.0157(12) -0.0010(10) 0.0048(10) 0.0018(10) N1 0.0191(15) 0.0139(14) 0.0136(14) -0.0005(12) 0.0011(11) -0.0009(12) N2 0.0261(16) 0.0148(13) 0.0199(16) 0.0023(12) 0.0083(12) 0.0035(12) C1 0.0157(17) 0.0202(18) 0.0137(17) -0.0022(14) 0.0014(13) 0.0037(14) C2 0.0125(18) 0.0225(19) 0.0132(18) 0.0043(14) -0.0017(13) 0.0016(14) C3 0.0154(18) 0.0131(16) 0.0207(18) 0.0016(15) -0.0014(14) 0.0006(14) C4 0.0180(18) 0.0156(17) 0.0156(17) -0.0029(14) -0.0022(13) 0.0022(14) C5 0.0145(17) 0.0156(16) 0.0169(17) 0.0022(15) -0.0006(13) -0.0019(14) C6 0.0131(17) 0.0129(16) 0.0169(18) -0.0010(14) -0.0023(13) 0.0014(13) C7 0.0195(17) 0.0120(17) 0.0172(17) 0.0003(13) 0.0002(14) 0.0006(13) C8 0.0139(17) 0.0140(17) 0.0138(16) -0.0017(13) 0.0023(13) -0.0009(13) C9 0.0092(17) 0.0174(17) 0.024(2) -0.0031(15) 0.0007(14) -0.0027(14) C10 0.0170(18) 0.0151(17) 0.0232(18) -0.0003(14) 0.0032(14) 0.0035(14) C11 0.0153(17) 0.0184(18) 0.0209(17) 0.0009(15) 0.0037(14) 0.0002(14) C12 0.031(2) 0.0186(17) 0.0190(18) 0.0061(15) 0.0033(14) 0.0013(16) C13 0.0217(18) 0.0253(19) 0.0153(17) 0.0035(15) 0.0050(13) 0.0002(15) C14 0.0212(18) 0.0208(18) 0.0121(17) 0.0042(14) -0.0008(13) -0.0004(14) C15 0.029(2) 0.0201(18) 0.0185(18) 0.0069(15) 0.0077(15) 0.0029(15) C16 0.0199(19) 0.0228(18) 0.026(2) -0.0006(16) 0.0052(14) 0.0025(16) C17 0.0180(17) 0.0160(17) 0.0191(18) -0.0002(14) 0.0023(13) 0.0024(14) C18 0.0150(17) 0.0173(16) 0.0143(16) 0.0018(14) 0.0016(13) -0.0012(14) C19 0.0192(18) 0.0177(17) 0.0175(18) 0.0008(14) 0.0004(14) -0.0002(14) C20 0.0240(19) 0.0207(17) 0.0149(17) 0.0023(15) 0.0009(14) -0.0048(15) C21 0.0239(18) 0.0161(16) 0.0152(18) -0.0016(14) 0.0042(14) -0.0020(15) C22 0.0217(19) 0.0214(18) 0.0179(18) 0.0015(14) 0.0037(14) 0.0039(15) C23 0.037(2) 0.0165(17) 0.027(2) -0.0022(17) 0.0024(16) -0.0043(16) O5 0.0634(19) 0.0222(14) 0.0201(13) 0.0018(11) 0.0065(12) 0.0171(13) O6 0.0478(17) 0.0281(14) 0.0170(13) 0.0022(11) -0.0031(11) 0.0052(12) O7 0.0458(17) 0.0177(13) 0.0391(15) 0.0000(12) -0.0047(12) 0.0046(12) O8 0.0504(17) 0.0220(13) 0.0202(14) -0.0042(11) -0.0073(11) -0.0023(12) N3 0.0361(18) 0.0200(16) 0.0187(15) -0.0016(13) -0.0085(13) 0.0039(13) C24 0.0197(19) 0.0212(19) 0.0206(19) 0.0009(16) 0.0031(14) -0.0018(15) C25 0.032(2) 0.0193(17) 0.0187(19) 0.0003(15) -0.0002(15) 0.0057(16) C26 0.042(2) 0.033(2) 0.030(2) 0.0002(18) 0.0157(18) 0.0054(19) C27 0.028(2) 0.026(2) 0.023(2) -0.0019(17) 0.0016(15) 0.0040(17) C28 0.041(2) 0.0284(19) 0.025(2) -0.0128(17) -0.0004(17) -0.0051(19) C29 0.053(3) 0.070(3) 0.056(3) -0.039(3) -0.001(2) 0.009(3) C30 0.049(3) 0.048(3) 0.041(2) -0.008(2) -0.0045(19) -0.017(2) C31 0.073(3) 0.049(3) 0.025(2) -0.008(2) -0.012(2) -0.003(2) O33 0.0506(18) 0.0514(16) 0.0339(15) 0.0146(14) 0.0177(13) 0.0235(15) C34 0.040(3) 0.054(3) 0.067(3) 0.005(2) -0.002(2) 0.017(2) C32 0.092(4) 0.061(3) 0.044(3) -0.010(3) 0.005(3) 0.022(3) C33 0.035(2) 0.031(2) 0.033(2) 0.0028(17) 0.0155(18) 0.0063(18) O1W 0.0552(18) 0.0331(14) 0.0253(14) 0.0076(12) -0.0048(12) -0.0132(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C12 1.438(4) . ? O1 C11 1.439(3) . ? O2 C2 1.378(4) . ? O2 C22 1.443(3) . ? O3 C3 1.369(3) . ? O3 C23 1.427(4) . ? O4 C9 1.245(3) . ? N1 C9 1.361(4) . ? N1 C6 1.432(4) . ? N1 C8 1.487(4) . ? N2 C16 1.508(4) . ? N2 C15 1.514(4) . ? N2 C21 1.528(4) . ? N2 H2 0.9300 . ? C1 C2 1.375(4) . ? C1 C6 1.397(4) . ? C1 H1 0.9500 . ? C2 C3 1.414(4) . ? C3 C4 1.398(4) . ? C4 C5 1.401(4) . ? C4 H4 0.9500 . ? C5 C6 1.382(4) . ? C5 C7 1.521(4) . ? C7 C17 1.545(4) . ? C7 C21 1.546(4) . ? C7 C8 1.569(4) . ? C8 C18 1.528(4) . ? C8 H8 1.0000 . ? C9 C10 1.511(4) . ? C10 C11 1.544(4) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C18 1.536(4) . ? C11 H11 1.0000 . ? C12 C13 1.507(4) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.340(4) . ? C13 H13 0.9500 . ? C14 C15 1.498(4) . ? C14 C19 1.517(4) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 C17 1.518(4) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 C19 1.535(4) . ? C18 H18 1.0000 . ? C19 C20 1.548(4) . ? C19 H19 1.0000 . ? C20 C21 1.526(4) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C21 H21 1.0000 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? O5 C24 1.262(4) . ? O6 C24 1.239(4) . ? O7 C27 1.225(4) . ? O8 C27 1.341(4) . ? O8 C28 1.483(4) . ? N3 C27 1.350(4) . ? N3 C25 1.472(4) . ? N3 H3 0.8800 . ? C24 C25 1.533(4) . ? C25 C26 1.527(5) . ? C25 H25 1.0000 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? C28 C29 1.508(5) . ? C28 C30 1.513(5) . ? C28 C31 1.523(5) . ? C29 H29A 0.9800 . ? C29 H29B 0.9800 . ? C29 H29C 0.9800 . ? C30 H30A 0.9800 . ? C30 H30B 0.9800 . ? C30 H30C 0.9800 . ? C31 H31A 0.9800 . ? C31 H31B 0.9800 . ? C31 H31C 0.9800 . ? O33 C33 1.425(4) . ? O33 H33 0.7421 . ? C34 C33 1.501(5) . ? C34 H34A 0.9800 . ? C34 H34B 0.9800 . ? C34 H34C 0.9800 . ? C32 C33 1.494(5) . ? C32 H32A 0.9800 . ? C32 H32B 0.9800 . ? C32 H32C 0.9800 . ? C33 H33A 1.0000 . ? O1W H11W 0.9937 . ? O1W H12W 0.8343 . ? 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 C12 O1 C11 116.0(2) . . ? C2 O2 C22 115.0(2) . . ? C3 O3 C23 116.9(2) . . ? C9 N1 C6 126.6(3) . . ? C9 N1 C8 119.7(2) . . ? C6 N1 C8 109.3(2) . . ? C16 N2 C15 112.9(2) . . ? C16 N2 C21 107.6(2) . . ? C15 N2 C21 114.2(2) . . ? C16 N2 H2 107.2 . . ? C15 N2 H2 107.2 . . ? C21 N2 H2 107.2 . . ? C2 C1 C6 117.7(3) . . ? C2 C1 H1 121.1 . . ? C6 C1 H1 121.1 . . ? C1 C2 O2 123.3(3) . . ? C1 C2 C3 121.6(3) . . ? O2 C2 C3 115.1(3) . . ? O3 C3 C4 125.0(3) . . ? O3 C3 C2 115.6(3) . . ? C4 C3 C2 119.5(3) . . ? C3 C4 C5 119.0(3) . . ? C3 C4 H4 120.5 . . ? C5 C4 H4 120.5 . . ? C6 C5 C4 119.8(3) . . ? C6 C5 C7 110.6(3) . . ? C4 C5 C7 129.4(3) . . ? C5 C6 C1 122.2(3) . . ? C5 C6 N1 110.1(3) . . ? C1 C6 N1 127.7(3) . . ? C5 C7 C17 111.8(2) . . ? C5 C7 C21 116.9(2) . . ? C17 C7 C21 101.7(2) . . ? C5 C7 C8 102.1(2) . . ? C17 C7 C8 111.2(2) . . ? C21 C7 C8 113.3(2) . . ? N1 C8 C18 106.0(2) . . ? N1 C8 C7 104.6(2) . . ? C18 C8 C7 117.3(3) . . ? N1 C8 H8 109.5 . . ? C18 C8 H8 109.5 . . ? C7 C8 H8 109.5 . . ? O4 C9 N1 123.2(3) . . ? O4 C9 C10 121.5(3) . . ? N1 C9 C10 115.3(3) . . ? C9 C10 C11 117.3(2) . . ? C9 C10 H10A 108.0 . . ? C11 C10 H10A 108.0 . . ? C9 C10 H10B 108.0 . . ? C11 C10 H10B 108.0 . . ? H10A C10 H10B 107.2 . . ? O1 C11 C18 114.9(2) . . ? O1 C11 C10 103.6(2) . . ? C18 C11 C10 111.0(2) . . ? O1 C11 H11 109.1 . . ? C18 C11 H11 109.1 . . ? C10 C11 H11 109.1 . . ? O1 C12 C13 110.6(2) . . ? O1 C12 H12A 109.5 . . ? C13 C12 H12A 109.5 . . ? O1 C12 H12B 109.5 . . ? C13 C12 H12B 109.5 . . ? H12A C12 H12B 108.1 . . ? C14 C13 C12 121.2(3) . . ? C14 C13 H13 119.4 . . ? C12 C13 H13 119.4 . . ? C13 C14 C15 121.1(3) . . ? C13 C14 C19 123.0(3) . . ? C15 C14 C19 115.8(3) . . ? C14 C15 N2 111.2(2) . . ? C14 C15 H15A 109.4 . . ? N2 C15 H15A 109.4 . . ? C14 C15 H15B 109.4 . . ? N2 C15 H15B 109.4 . . ? H15A C15 H15B 108.0 . . ? N2 C16 C17 105.2(2) . . ? N2 C16 H16A 110.7 . . ? C17 C16 H16A 110.7 . . ? N2 C16 H16B 110.7 . . ? C17 C16 H16B 110.7 . . ? H16A C16 H16B 108.8 . . ? C16 C17 C7 103.2(2) . . ? C16 C17 H17A 111.1 . . ? C7 C17 H17A 111.1 . . ? C16 C17 H17B 111.1 . . ? C7 C17 H17B 111.1 . . ? H17A C17 H17B 109.1 . . ? C8 C18 C19 113.0(3) . . ? C8 C18 C11 107.7(2) . . ? C19 C18 C11 117.9(2) . . ? C8 C18 H18 105.8 . . ? C19 C18 H18 105.8 . . ? C11 C18 H18 105.8 . . ? C14 C19 C18 114.4(2) . . ? C14 C19 C20 109.5(3) . . ? C18 C19 C20 106.4(2) . . ? C14 C19 H19 108.8 . . ? C18 C19 H19 108.8 . . ? C20 C19 H19 108.8 . . ? C21 C20 C19 108.6(3) . . ? C21 C20 H20A 110.0 . . ? C19 C20 H20A 110.0 . . ? C21 C20 H20B 110.0 . . ? C19 C20 H20B 110.0 . . ? H20A C20 H20B 108.4 . . ? C20 C21 N2 110.1(2) . . ? C20 C21 C7 115.9(2) . . ? N2 C21 C7 104.8(2) . . ? C20 C21 H21 108.6 . . ? N2 C21 H21 108.6 . . ? C7 C21 H21 108.6 . . ? O2 C22 H22A 109.5 . . ? O2 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? O2 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? O3 C23 H23A 109.5 . . ? O3 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? O3 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C27 O8 C28 122.4(3) . . ? C27 N3 C25 125.0(3) . . ? C27 N3 H3 117.5 . . ? C25 N3 H3 117.5 . . ? O6 C24 O5 125.7(3) . . ? O6 C24 C25 120.5(3) . . ? O5 C24 C25 113.7(3) . . ? N3 C25 C26 111.0(3) . . ? N3 C25 C24 111.4(3) . . ? C26 C25 C24 109.5(3) . . ? N3 C25 H25 108.3 . . ? C26 C25 H25 108.3 . . ? C24 C25 H25 108.3 . . ? C25 C26 H26A 109.5 . . ? C25 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C25 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? O7 C27 O8 125.4(3) . . ? O7 C27 N3 124.3(3) . . ? O8 C27 N3 110.3(3) . . ? O8 C28 C29 109.8(3) . . ? O8 C28 C30 110.5(3) . . ? C29 C28 C30 112.8(3) . . ? O8 C28 C31 101.5(3) . . ? C29 C28 C31 111.3(3) . . ? C30 C28 C31 110.5(3) . . ? C28 C29 H29A 109.5 . . ? C28 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C28 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C28 C30 H30A 109.5 . . ? C28 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C28 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? C28 C31 H31A 109.5 . . ? C28 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? C28 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? C33 O33 H33 106.5 . . ? C33 C34 H34A 109.5 . . ? C33 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? C33 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? C33 C32 H32A 109.5 . . ? C33 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C33 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? O33 C33 C32 111.0(3) . . ? O33 C33 C34 106.6(3) . . ? C32 C33 C34 112.3(3) . . ? O33 C33 H33A 108.9 . . ? C32 C33 H33A 108.9 . . ? C34 C33 H33A 108.9 . . ? H11W O1W H12W 108.2 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 O2 -178.6(3) . . . . ? C6 C1 C2 C3 0.8(5) . . . . ? C22 O2 C2 C1 -1.3(4) . . . . ? C22 O2 C2 C3 179.3(3) . . . . ? C23 O3 C3 C4 10.5(4) . . . . ? C23 O3 C3 C2 -170.3(3) . . . . ? C1 C2 C3 O3 177.2(3) . . . . ? O2 C2 C3 O3 -3.4(4) . . . . ? C1 C2 C3 C4 -3.5(5) . . . . ? O2 C2 C3 C4 175.9(3) . . . . ? O3 C3 C4 C5 -177.4(3) . . . . ? C2 C3 C4 C5 3.4(4) . . . . ? C3 C4 C5 C6 -0.6(5) . . . . ? C3 C4 C5 C7 -174.7(3) . . . . ? C4 C5 C6 C1 -2.1(5) . . . . ? C7 C5 C6 C1 173.0(3) . . . . ? C4 C5 C6 N1 176.3(3) . . . . ? C7 C5 C6 N1 -8.6(4) . . . . ? C2 C1 C6 C5 2.0(5) . . . . ? C2 C1 C6 N1 -176.1(3) . . . . ? C9 N1 C6 C5 -159.7(3) . . . . ? C8 N1 C6 C5 -3.6(3) . . . . ? C9 N1 C6 C1 18.6(5) . . . . ? C8 N1 C6 C1 174.8(3) . . . . ? C6 C5 C7 C17 -102.9(3) . . . . ? C4 C5 C7 C17 71.7(4) . . . . ? C6 C5 C7 C21 140.5(3) . . . . ? C4 C5 C7 C21 -45.0(4) . . . . ? C6 C5 C7 C8 16.2(3) . . . . ? C4 C5 C7 C8 -169.3(3) . . . . ? C9 N1 C8 C18 46.9(3) . . . . ? C6 N1 C8 C18 -111.2(3) . . . . ? C9 N1 C8 C7 171.5(2) . . . . ? C6 N1 C8 C7 13.5(3) . . . . ? C5 C7 C8 N1 -17.3(3) . . . . ? C17 C7 C8 N1 102.2(3) . . . . ? C21 C7 C8 N1 -143.9(2) . . . . ? C5 C7 C8 C18 99.8(3) . . . . ? C17 C7 C8 C18 -140.7(3) . . . . ? C21 C7 C8 C18 -26.8(4) . . . . ? C6 N1 C9 O4 -21.9(5) . . . . ? C8 N1 C9 O4 -175.9(3) . . . . ? C6 N1 C9 C10 160.0(3) . . . . ? C8 N1 C9 C10 6.1(4) . . . . ? O4 C9 C10 C11 144.9(3) . . . . ? N1 C9 C10 C11 -37.0(4) . . . . ? C12 O1 C11 C18 -66.5(3) . . . . ? C12 O1 C11 C10 172.2(2) . . . . ? C9 C10 C11 O1 134.6(3) . . . . ? C9 C10 C11 C18 10.8(4) . . . . ? C11 O1 C12 C13 88.8(3) . . . . ? O1 C12 C13 C14 -63.5(4) . . . . ? C12 C13 C14 C15 175.9(3) . . . . ? C12 C13 C14 C19 -5.2(5) . . . . ? C13 C14 C15 N2 -130.6(3) . . . . ? C19 C14 C15 N2 50.4(4) . . . . ? C16 N2 C15 C14 79.1(3) . . . . ? C21 N2 C15 C14 -44.3(3) . . . . ? C15 N2 C16 C17 -141.6(2) . . . . ? C21 N2 C16 C17 -14.6(3) . . . . ? N2 C16 C17 C7 35.3(3) . . . . ? C5 C7 C17 C16 -167.4(2) . . . . ? C21 C7 C17 C16 -41.9(3) . . . . ? C8 C7 C17 C16 79.0(3) . . . . ? N1 C8 C18 C19 157.8(2) . . . . ? C7 C8 C18 C19 41.5(4) . . . . ? N1 C8 C18 C11 -70.2(3) . . . . ? C7 C8 C18 C11 173.5(2) . . . . ? O1 C11 C18 C8 -76.0(3) . . . . ? C10 C11 C18 C8 41.1(3) . . . . ? O1 C11 C18 C19 53.2(4) . . . . ? C10 C11 C18 C19 170.3(3) . . . . ? C13 C14 C19 C18 62.0(4) . . . . ? C15 C14 C19 C18 -119.0(3) . . . . ? C13 C14 C19 C20 -178.7(3) . . . . ? C15 C14 C19 C20 0.3(4) . . . . ? C8 C18 C19 C14 60.2(3) . . . . ? C11 C18 C19 C14 -66.6(4) . . . . ? C8 C18 C19 C20 -60.8(3) . . . . ? C11 C18 C19 C20 172.4(3) . . . . ? C14 C19 C20 C21 -56.5(3) . . . . ? C18 C19 C20 C21 67.5(3) . . . . ? C19 C20 C21 N2 62.3(3) . . . . ? C19 C20 C21 C7 -56.5(3) . . . . ? C16 N2 C21 C20 -137.1(3) . . . . ? C15 N2 C21 C20 -10.9(3) . . . . ? C16 N2 C21 C7 -11.7(3) . . . . ? C15 N2 C21 C7 114.5(3) . . . . ? C5 C7 C21 C20 -83.5(3) . . . . ? C17 C7 C21 C20 154.4(3) . . . . ? C8 C7 C21 C20 34.9(4) . . . . ? C5 C7 C21 N2 154.9(2) . . . . ? C17 C7 C21 N2 32.8(3) . . . . ? C8 C7 C21 N2 -86.7(3) . . . . ? C27 N3 C25 C26 92.1(4) . . . . ? C27 N3 C25 C24 -145.6(3) . . . . ? O6 C24 C25 N3 -22.0(4) . . . . ? O5 C24 C25 N3 160.2(3) . . . . ? O6 C24 C25 C26 101.1(3) . . . . ? O5 C24 C25 C26 -76.7(4) . . . . ? C28 O8 C27 O7 -2.4(5) . . . . ? C28 O8 C27 N3 176.1(3) . . . . ? C25 N3 C27 O7 -175.4(3) . . . . ? C25 N3 C27 O8 6.0(4) . . . . ? C27 O8 C28 C29 69.2(4) . . . . ? C27 O8 C28 C30 -55.8(4) . . . . ? C27 O8 C28 C31 -173.0(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2 O5 0.93 1.68 2.584(3) 162.6 . N3 H3 O6 0.88 2.46 2.756(3) 100.3 . O33 H33 O7 0.74 2.09 2.821(3) 170.4 . O1W H11W O4 0.99 1.86 2.843(3) 170.3 4_655 O1W H12W O6 0.83 1.93 2.765(3) 175.0 . _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.173 _refine_diff_density_min -0.170 _refine_diff_density_rms 0.039