# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Bialonska, Agata' _publ_contact_author_email agata.bialonska@gmail.com _publ_section_title ; hen a host becomes a guest competition between decreasing of hydrophobic spaces and supramolecular synthon propagation ; loop_ _publ_author_name A.Bialonska Z.Ciunik # Attachment '- bialonska_cif.txt' data_1 _database_code_depnum_ccdc_archive 'CCDC 783801' #TrackingRef '- bialonska_cif.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; brucinium N-(4-nitrobenzoyl)-D-asparaginate heptahydrate ; _chemical_name_common 'brucinium N-(4-nitrobenzoyl)-D-asparaginate heptahydrate' _chemical_melting_point ? _chemical_formula_moiety 'C23 H27 N2 O4, C11 H10 N3 O6, 7(H2 O)' _chemical_formula_sum 'C34 H51 N5 O17' _chemical_formula_weight 801.80 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 7.119(2) _cell_length_b 12.530(3) _cell_length_c 41.520(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3703.6(14) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 19273 _cell_measurement_theta_min 2.90 _cell_measurement_theta_max 28.29 _exptl_crystal_description plate _exptl_crystal_colour orange _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.438 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1704 _exptl_absorpt_coefficient_mu 0.116 _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 24975 _diffrn_reflns_av_R_equivalents 0.1187 _diffrn_reflns_av_sigmaI/netI 0.0995 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -53 _diffrn_reflns_limit_l_max 52 _diffrn_reflns_theta_min 2.90 _diffrn_reflns_theta_max 27.50 _reflns_number_total 4773 _reflns_number_gt 3072 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.31.8 (release 12-01-2007 CrysAlis171 .NET) (compiled Jan 12 2007,17:49:11) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.8 (release 12-01-2007 CrysAlis171 .NET) (compiled Jan 12 2007,17:49:11) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.8 (release 12-01-2007 CrysAlis171 .NET) (compiled Jan 12 2007,17:49:11) ; _computing_structure_solution ; SHELXS-97 (Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.) ; _computing_structure_refinement ; SHELXL-97 (Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.) ; _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0680P)^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 4773 _refine_ls_number_parameters 505 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1033 _refine_ls_R_factor_gt 0.0621 _refine_ls_wR_factor_ref 0.1462 _refine_ls_wR_factor_gt 0.1289 _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_restrained_S_all 1.023 _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 O5 O 0.3386(5) -0.0049(3) 0.20246(8) 0.0270(8) Uani 1 1 d . . . O6 O 0.5774(5) -0.1065(3) 0.21850(8) 0.0232(8) Uani 1 1 d . . . O7 O 0.8724(5) 0.2383(3) 0.24599(9) 0.0295(9) Uani 1 1 d . . . O8 O 0.6710(5) 0.0395(3) 0.15367(8) 0.0250(8) Uani 1 1 d . . . O9 O 0.6769(6) 0.5528(3) 0.07327(9) 0.0348(10) Uani 1 1 d . . . O10 O 0.6525(7) 0.4298(3) 0.03657(9) 0.0424(11) Uani 1 1 d . . . N3 N 0.6008(6) 0.1614(3) 0.19163(10) 0.0238(10) Uani 1 1 d . . . H37 H 0.5644 0.2270 0.1958 0.029 Uiso 1 1 calc R . . N4 N 1.1015(6) 0.1711(4) 0.21502(10) 0.0310(11) Uani 1 1 d . . . H471 H 1.1677 0.2301 0.2168 0.037 Uiso 1 1 calc R . . H472 H 1.1449 0.1174 0.2036 0.037 Uiso 1 1 calc R . . N5 N 0.6601(6) 0.4582(3) 0.06486(11) 0.0286(10) Uani 1 1 d . . . C24 C 0.5040(7) -0.0178(4) 0.21190(12) 0.0245(12) Uani 1 1 d . . . C25 C 0.6217(7) 0.0841(4) 0.21822(13) 0.0246(12) Uani 1 1 d . . . H25 H 0.5687 0.1186 0.2379 0.029 Uiso 1 1 calc R . . C26 C 0.8267(7) 0.0611(4) 0.22516(13) 0.0257(12) Uani 1 1 d . . . H26A H 0.8805 0.0192 0.2072 0.031 Uiso 1 1 calc R . . H26B H 0.8364 0.0176 0.2450 0.031 Uiso 1 1 calc R . . C27 C 0.9389(7) 0.1632(4) 0.22940(12) 0.0238(11) Uani 1 1 d . . . C28 C 0.6365(7) 0.1328(4) 0.16139(12) 0.0215(11) Uani 1 1 d . . . C29 C 0.6360(6) 0.2206(4) 0.13677(12) 0.0196(11) Uani 1 1 d . . . C3O C 0.5953(7) 0.1945(4) 0.10475(12) 0.0217(11) Uani 1 1 d . . . H3O H 0.5635 0.1233 0.0991 0.026 Uiso 1 1 calc R . . C31 C 0.6017(7) 0.2724(4) 0.08141(12) 0.0239(12) Uani 1 1 d . . . H31 H 0.5738 0.2559 0.0596 0.029 Uiso 1 1 calc R . . C32 C 0.6502(7) 0.3766(4) 0.09047(13) 0.0242(12) Uani 1 1 d . . . C33 C 0.6919(7) 0.4046(4) 0.12124(12) 0.0221(11) Uani 1 1 d . . . H33 H 0.7251 0.4758 0.1267 0.027 Uiso 1 1 calc R . . C34 C 0.6840(7) 0.3246(4) 0.14460(12) 0.0238(11) Uani 1 1 d . . . H34 H 0.7122 0.3419 0.1664 0.029 Uiso 1 1 calc R . . O1W O 0.8325(6) 0.5790(3) 0.17881(10) 0.0439(11) Uani 1 1 d . . . H11W H 0.8450 0.5356 0.1953 0.066 Uiso 1 1 d R . . H12W H 0.8095 0.6423 0.1863 0.066 Uiso 1 1 d R . . O2W O 0.4434(6) 0.5329(3) 0.18149(9) 0.0398(10) Uani 1 1 d . . . H21W H 0.3912 0.5919 0.1885 0.060 Uiso 1 1 d R . . H22W H 0.5644 0.5384 0.1841 0.060 Uiso 1 1 d R . . O3W O 0.8394(7) 0.4542(3) 0.23442(11) 0.0518(12) Uani 1 1 d . . . H31W H 0.8727 0.3864 0.2331 0.078 Uiso 1 1 d R . . H32W H 0.7822 0.4641 0.2530 0.078 Uiso 1 1 d R . . O5W O 0.8989(5) 0.7908(3) 0.19984(8) 0.0281(9) Uani 1 1 d . . . H51W H 0.7995 0.8268 0.2050 0.042 Uiso 1 1 d R . . H52W H 0.9836 0.8006 0.2146 0.042 Uiso 1 1 d R . . O6W O 0.3819(5) 0.3446(3) 0.21534(9) 0.0295(9) Uani 1 1 d . . . H61W H 0.3855 0.3513 0.2361 0.044 Uiso 1 1 d R . . H62W H 0.3947 0.4074 0.2067 0.044 Uiso 1 1 d R . . O7W O 0.3368(5) 0.7395(3) 0.19805(8) 0.0269(8) Uani 1 1 d . . . H71W H 0.2723 0.7354 0.2157 0.040 Uiso 1 1 d R . . H72W H 0.4203 0.7881 0.1998 0.040 Uiso 1 1 d R . . O1 O 0.0639(5) 1.0136(2) 0.03871(7) 0.0184(7) Uani 1 1 d . . . O2 O 0.1634(5) 0.3154(2) 0.04393(8) 0.0251(8) Uani 1 1 d . . . O3 O 0.1579(5) 0.3253(3) 0.10633(8) 0.0250(8) Uani 1 1 d . . . O4 O 0.0642(5) 0.6728(3) -0.01085(8) 0.0223(8) Uani 1 1 d . . . N1 N 0.1572(6) 0.7098(3) 0.04052(9) 0.0180(9) Uani 1 1 d . . . N2 N 0.1926(5) 0.8494(3) 0.14357(10) 0.0177(9) Uani 1 1 d . . . H24 H 0.2135 0.8308 0.1650 0.021 Uiso 1 1 calc R . . C1 C 0.1556(7) 0.5072(4) 0.03804(11) 0.0181(10) Uani 1 1 d . . . H1 H 0.1519 0.5030 0.0152 0.022 Uiso 1 1 calc R . . C2 C 0.1595(7) 0.4163(4) 0.05693(12) 0.0218(11) Uani 1 1 d . . . C3 C 0.1617(7) 0.4210(4) 0.09058(12) 0.0202(11) Uani 1 1 d . . . C4 C 0.1696(7) 0.5195(4) 0.10612(11) 0.0177(10) Uani 1 1 d . . . H4 H 0.1765 0.5238 0.1289 0.021 Uiso 1 1 calc R . . C5 C 0.1673(7) 0.6119(4) 0.08724(12) 0.0191(11) Uani 1 1 d . . . C6 C 0.1572(7) 0.6051(4) 0.05394(12) 0.0180(10) Uani 1 1 d . . . C7 C 0.1949(6) 0.7268(4) 0.09809(11) 0.0149(10) Uani 1 1 d . . . C8 C 0.1510(7) 0.7903(4) 0.06700(11) 0.0167(10) Uani 1 1 d . . . H8 H 0.2509 0.8451 0.0634 0.020 Uiso 1 1 calc R . . C9 C 0.0917(6) 0.7380(4) 0.01097(11) 0.0199(11) Uani 1 1 d . . . C10 C 0.0621(7) 0.8562(4) 0.00661(11) 0.0190(11) Uani 1 1 d . . . H10A H -0.0124 0.8673 -0.0133 0.023 Uiso 1 1 calc R . . H10B H 0.1862 0.8900 0.0032 0.023 Uiso 1 1 calc R . . C11 C -0.0369(7) 0.9150(3) 0.03440(11) 0.0181(11) Uani 1 1 d . . . H11 H -0.1686 0.9317 0.0277 0.022 Uiso 1 1 calc R . . C12 C -0.0233(8) 1.0858(4) 0.06085(12) 0.0234(12) Uani 1 1 d . . . H12A H -0.1611 1.0751 0.0606 0.028 Uiso 1 1 calc R . . H12B H 0.0031 1.1603 0.0543 0.028 Uiso 1 1 calc R . . C13 C 0.0515(7) 1.0663(4) 0.09442(12) 0.0209(11) Uani 1 1 d . . . H3 H 0.1269 1.1193 0.1044 0.025 Uiso 1 1 calc R . . C14 C 0.0140(7) 0.9769(4) 0.11019(12) 0.0192(11) Uani 1 1 d . . . C15 C 0.0931(7) 0.9555(4) 0.14307(12) 0.0209(11) Uani 1 1 d . . . H15A H -0.0097 0.9552 0.1591 0.025 Uiso 1 1 calc R . . H15B H 0.1824 1.0129 0.1489 0.025 Uiso 1 1 calc R . . C16 C 0.3816(6) 0.8544(4) 0.12669(12) 0.0203(11) Uani 1 1 d . . . H16A H 0.4848 0.8639 0.1424 0.024 Uiso 1 1 calc R . . H16B H 0.3852 0.9138 0.1110 0.024 Uiso 1 1 calc R . . C17 C 0.3969(6) 0.7470(4) 0.10973(12) 0.0194(11) Uani 1 1 d . . . H17A H 0.4386 0.6905 0.1248 0.023 Uiso 1 1 calc R . . H17B H 0.4854 0.7506 0.0914 0.023 Uiso 1 1 calc R . . C18 C -0.0430(6) 0.8431(4) 0.06440(11) 0.0166(10) Uani 1 1 d . . . H18 H -0.1325 0.7842 0.0591 0.020 Uiso 1 1 calc R . . C19 C -0.1117(6) 0.8899(3) 0.09682(11) 0.0172(10) Uani 1 1 d . . . H19 H -0.2412 0.9193 0.0939 0.021 Uiso 1 1 calc R . . C20 C -0.1197(6) 0.7960(4) 0.12058(11) 0.0151(10) Uani 1 1 d . . . H20A H -0.1813 0.8188 0.1408 0.018 Uiso 1 1 calc R . . H20B H -0.1939 0.7369 0.1112 0.018 Uiso 1 1 calc R . . C21 C 0.0785(6) 0.7585(4) 0.12755(11) 0.0178(10) Uani 1 1 d . . . H21 H 0.0727 0.6964 0.1427 0.021 Uiso 1 1 calc R . . C22 C 0.1881(9) 0.3079(4) 0.00947(12) 0.0340(14) Uani 1 1 d . . . H22A H 0.1883 0.2327 0.0030 0.051 Uiso 1 1 calc R . . H22B H 0.3078 0.3409 0.0034 0.051 Uiso 1 1 calc R . . H22C H 0.0849 0.3452 -0.0014 0.051 Uiso 1 1 calc R . . C23 C 0.1755(8) 0.3293(4) 0.14086(12) 0.0257(12) Uani 1 1 d . . . H23A H 0.1700 0.2567 0.1496 0.039 Uiso 1 1 calc R . . H23B H 0.0725 0.3718 0.1499 0.039 Uiso 1 1 calc R . . H23C H 0.2959 0.3621 0.1466 0.039 Uiso 1 1 calc R . . O4W O -0.0290(5) 0.4913(3) -0.04896(9) 0.0334(9) Uani 1 1 d . . . H41W H 0.0011 0.5486 -0.0382 0.050 Uiso 1 1 d R . . H42W H -0.1506 0.4892 -0.0499 0.050 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 O5 0.0188(19) 0.0266(19) 0.036(2) 0.0036(16) -0.0028(17) 0.0025(17) O6 0.0184(18) 0.0198(18) 0.031(2) 0.0025(15) -0.0017(16) 0.0042(15) O7 0.026(2) 0.024(2) 0.038(2) -0.0041(17) 0.0034(18) 0.0006(17) O8 0.0231(19) 0.0166(18) 0.035(2) -0.0002(15) 0.0042(17) 0.0004(16) O9 0.049(3) 0.019(2) 0.037(2) 0.0032(17) -0.001(2) 0.0014(19) O10 0.067(3) 0.034(2) 0.026(2) 0.0033(18) -0.005(2) 0.001(2) N3 0.027(2) 0.016(2) 0.028(2) 0.0037(18) 0.000(2) -0.0001(19) N4 0.028(3) 0.035(3) 0.030(3) -0.007(2) 0.005(2) -0.004(2) N5 0.028(3) 0.023(2) 0.034(3) 0.004(2) -0.004(2) 0.003(2) C24 0.021(3) 0.030(3) 0.022(3) -0.005(2) 0.000(2) 0.000(2) C25 0.020(3) 0.024(3) 0.030(3) 0.004(2) 0.001(2) 0.000(2) C26 0.024(3) 0.024(3) 0.030(3) -0.001(2) -0.001(3) 0.000(2) C27 0.021(3) 0.027(3) 0.023(3) 0.004(2) -0.002(2) 0.000(2) C28 0.009(2) 0.025(3) 0.031(3) 0.004(2) 0.000(2) -0.002(2) C29 0.012(2) 0.021(3) 0.026(3) -0.001(2) 0.001(2) 0.001(2) C3O 0.020(3) 0.016(2) 0.029(3) -0.001(2) 0.001(2) 0.000(2) C31 0.023(3) 0.027(3) 0.022(3) -0.003(2) -0.001(2) 0.004(2) C32 0.020(3) 0.018(3) 0.034(3) 0.002(2) 0.000(2) 0.001(2) C33 0.022(3) 0.017(3) 0.027(3) -0.004(2) 0.000(2) 0.001(2) C34 0.020(3) 0.031(3) 0.021(3) 0.001(2) 0.000(2) -0.004(2) O1W 0.055(3) 0.032(2) 0.045(3) -0.0009(19) 0.008(2) -0.007(2) O2W 0.042(2) 0.027(2) 0.051(3) -0.0085(19) 0.001(2) -0.0029(19) O3W 0.056(3) 0.041(2) 0.059(3) 0.001(2) 0.004(3) -0.001(2) O5W 0.0230(19) 0.028(2) 0.033(2) -0.0007(16) -0.0024(17) 0.0046(16) O6W 0.035(2) 0.0241(19) 0.030(2) -0.0029(16) -0.0012(18) -0.0051(17) O7W 0.0211(19) 0.0251(19) 0.034(2) -0.0005(16) -0.0025(17) -0.0072(17) O1 0.0207(17) 0.0122(16) 0.0223(17) -0.0003(14) 0.0045(14) -0.0003(14) O2 0.036(2) 0.0128(17) 0.026(2) -0.0032(14) 0.0068(17) -0.0004(17) O3 0.035(2) 0.0159(17) 0.0247(19) 0.0018(14) -0.0009(17) -0.0010(16) O4 0.0231(19) 0.0210(19) 0.0230(19) -0.0057(15) -0.0015(16) -0.0026(16) N1 0.018(2) 0.013(2) 0.022(2) -0.0027(16) 0.0025(19) 0.0028(17) N2 0.019(2) 0.016(2) 0.019(2) -0.0017(16) -0.0004(18) 0.0026(17) C1 0.021(3) 0.017(2) 0.017(2) -0.004(2) 0.001(2) 0.000(2) C2 0.019(3) 0.018(3) 0.029(3) -0.003(2) -0.001(2) -0.002(2) C3 0.014(2) 0.018(3) 0.029(3) 0.003(2) 0.003(2) -0.002(2) C4 0.017(2) 0.018(2) 0.018(2) -0.001(2) 0.002(2) -0.002(2) C5 0.012(2) 0.018(3) 0.028(3) -0.004(2) 0.002(2) 0.001(2) C6 0.012(2) 0.016(2) 0.026(3) 0.004(2) 0.000(2) 0.001(2) C7 0.011(2) 0.021(3) 0.013(2) -0.0008(19) -0.002(2) -0.003(2) C8 0.017(2) 0.016(2) 0.017(2) -0.0050(19) -0.004(2) -0.004(2) C9 0.011(2) 0.025(3) 0.024(3) -0.001(2) 0.002(2) -0.004(2) C10 0.021(3) 0.019(3) 0.017(3) 0.002(2) 0.003(2) -0.003(2) C11 0.018(3) 0.013(2) 0.023(3) -0.003(2) 0.002(2) -0.002(2) C12 0.030(3) 0.016(3) 0.024(3) 0.002(2) 0.006(2) 0.006(2) C13 0.020(3) 0.018(3) 0.024(3) -0.007(2) 0.003(2) 0.004(2) C14 0.016(2) 0.015(2) 0.026(3) -0.004(2) 0.002(2) 0.001(2) C15 0.017(2) 0.017(2) 0.029(3) -0.009(2) -0.001(2) 0.006(2) C16 0.010(2) 0.025(3) 0.026(3) -0.001(2) 0.003(2) 0.001(2) C17 0.016(2) 0.018(2) 0.024(3) -0.002(2) 0.000(2) -0.001(2) C18 0.015(2) 0.014(2) 0.021(3) -0.0015(19) -0.002(2) 0.001(2) C19 0.012(2) 0.015(2) 0.025(3) -0.003(2) -0.002(2) 0.0024(19) C20 0.012(2) 0.016(2) 0.017(2) -0.0030(19) 0.005(2) -0.0006(19) C21 0.017(2) 0.011(2) 0.026(3) 0.0000(19) -0.002(2) -0.004(2) C22 0.047(4) 0.021(3) 0.034(3) -0.006(2) 0.005(3) -0.004(3) C23 0.033(3) 0.015(2) 0.029(3) 0.007(2) -0.007(3) 0.001(2) O4W 0.0201(19) 0.034(2) 0.046(2) -0.0161(19) -0.0053(17) 0.0005(17) _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 O5 C24 1.252(6) . ? O6 C24 1.258(6) . ? O7 C27 1.259(6) . ? O8 C28 1.237(6) . ? O9 N5 1.241(5) . ? O10 N5 1.229(6) . ? N3 C28 1.330(6) . ? N3 C25 1.477(6) . ? N3 H37 0.8800 . ? N4 C27 1.307(7) . ? N4 H471 0.8800 . ? N4 H472 0.8800 . ? N5 C32 1.477(6) . ? C24 C25 1.550(7) . ? C25 C26 1.515(7) . ? C25 H25 1.0000 . ? C26 C27 1.518(7) . ? C26 H26A 0.9900 . ? C26 H26B 0.9900 . ? C28 C29 1.502(7) . ? C29 C34 1.386(7) . ? C29 C3O 1.399(7) . ? C3O C31 1.376(7) . ? C3O H3O 0.9500 . ? C31 C32 1.401(7) . ? C31 H31 0.9500 . ? C32 C33 1.358(7) . ? C33 C34 1.396(7) . ? C33 H33 0.9500 . ? C34 H34 0.9500 . ? O1W H11W 0.8792 . ? O1W H12W 0.8673 . ? O2W H21W 0.8767 . ? O2W H22W 0.8712 . ? O3W H31W 0.8848 . ? O3W H32W 0.8823 . ? O5W H51W 0.8660 . ? O5W H52W 0.8693 . ? O6W H61W 0.8669 . ? O6W H62W 0.8696 . ? O7W H71W 0.8671 . ? O7W H72W 0.8541 . ? O1 C12 1.431(5) . ? O1 C11 1.441(5) . ? O2 C2 1.375(6) . ? O2 C22 1.445(6) . ? O3 C3 1.366(6) . ? O3 C23 1.440(6) . ? O4 C9 1.236(6) . ? N1 C9 1.359(6) . ? N1 C6 1.426(6) . ? N1 C8 1.493(5) . ? N2 C15 1.506(6) . ? N2 C16 1.518(6) . ? N2 C21 1.550(6) . ? N2 H24 0.9300 . ? C1 C2 1.382(6) . ? C1 C6 1.393(6) . ? C1 H1 0.9500 . ? C2 C3 1.399(7) . ? C3 C4 1.394(6) . ? C4 C5 1.397(6) . ? C4 H4 0.9500 . ? C5 C6 1.387(7) . ? C5 C7 1.522(6) . ? C7 C21 1.530(6) . ? C7 C17 1.538(6) . ? C7 C8 1.548(6) . ? C8 C18 1.535(6) . ? C8 H8 1.0000 . ? C9 C10 1.507(7) . ? C10 C11 1.540(6) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C18 1.537(7) . ? C11 H11 1.0000 . ? C12 C13 1.512(7) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.325(6) . ? C13 H3 0.9500 . ? C14 C15 1.501(7) . ? C14 C19 1.515(6) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 C17 1.523(6) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 C19 1.547(6) . ? C18 H18 1.0000 . ? C19 C20 1.537(6) . ? C19 H19 1.0000 . ? C20 C21 1.515(6) . ? 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 . ? O4W H41W 0.8714 . ? O4W H42W 0.8671 . ? 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 C28 N3 C25 120.6(4) . . ? C28 N3 H37 119.7 . . ? C25 N3 H37 119.7 . . ? C27 N4 H471 120.0 . . ? C27 N4 H472 120.0 . . ? H471 N4 H472 120.0 . . ? O10 N5 O9 123.4(4) . . ? O10 N5 C32 119.0(4) . . ? O9 N5 C32 117.6(4) . . ? O5 C24 O6 125.0(5) . . ? O5 C24 C25 117.1(5) . . ? O6 C24 C25 117.8(4) . . ? N3 C25 C26 111.3(4) . . ? N3 C25 C24 111.1(4) . . ? C26 C25 C24 113.4(4) . . ? N3 C25 H25 106.9 . . ? C26 C25 H25 106.9 . . ? C24 C25 H25 106.9 . . ? C25 C26 C27 111.6(4) . . ? C25 C26 H26A 109.3 . . ? C27 C26 H26A 109.3 . . ? C25 C26 H26B 109.3 . . ? C27 C26 H26B 109.3 . . ? H26A C26 H26B 108.0 . . ? O7 C27 N4 121.8(5) . . ? O7 C27 C26 119.7(4) . . ? N4 C27 C26 118.5(5) . . ? O8 C28 N3 122.5(5) . . ? O8 C28 C29 121.1(5) . . ? N3 C28 C29 116.4(4) . . ? C34 C29 C3O 119.6(4) . . ? C34 C29 C28 121.9(4) . . ? C3O C29 C28 118.4(4) . . ? C31 C3O C29 119.8(5) . . ? C31 C3O H3O 120.1 . . ? C29 C3O H3O 120.1 . . ? C3O C31 C32 118.7(5) . . ? C3O C31 H31 120.7 . . ? C32 C31 H31 120.7 . . ? C33 C32 C31 123.2(5) . . ? C33 C32 N5 119.2(4) . . ? C31 C32 N5 117.6(5) . . ? C32 C33 C34 117.3(5) . . ? C32 C33 H33 121.3 . . ? C34 C33 H33 121.3 . . ? C29 C34 C33 121.5(5) . . ? C29 C34 H34 119.3 . . ? C33 C34 H34 119.3 . . ? H11W O1W H12W 107.9 . . ? H21W O2W H22W 108.2 . . ? H31W O3W H32W 108.3 . . ? H51W O5W H52W 108.7 . . ? H61W O6W H62W 108.6 . . ? H71W O7W H72W 109.9 . . ? C12 O1 C11 113.9(4) . . ? C2 O2 C22 116.8(4) . . ? C3 O3 C23 116.4(4) . . ? C9 N1 C6 126.3(4) . . ? C9 N1 C8 118.6(4) . . ? C6 N1 C8 109.5(4) . . ? C15 N2 C16 112.0(4) . . ? C15 N2 C21 113.3(4) . . ? C16 N2 C21 107.3(3) . . ? C15 N2 H24 108.0 . . ? C16 N2 H24 108.0 . . ? C21 N2 H24 108.0 . . ? C2 C1 C6 117.1(4) . . ? C2 C1 H1 121.4 . . ? C6 C1 H1 121.4 . . ? O2 C2 C1 122.3(4) . . ? O2 C2 C3 115.5(4) . . ? C1 C2 C3 122.2(4) . . ? O3 C3 C4 123.8(4) . . ? O3 C3 C2 116.2(4) . . ? C4 C3 C2 120.0(4) . . ? C3 C4 C5 118.2(4) . . ? C3 C4 H4 120.9 . . ? C5 C4 H4 120.9 . . ? C6 C5 C4 120.6(4) . . ? C6 C5 C7 111.1(4) . . ? C4 C5 C7 128.0(4) . . ? C5 C6 C1 121.8(4) . . ? C5 C6 N1 109.4(4) . . ? C1 C6 N1 128.7(4) . . ? C5 C7 C21 114.3(4) . . ? C5 C7 C17 111.7(4) . . ? C21 C7 C17 102.3(4) . . ? C5 C7 C8 102.3(4) . . ? C21 C7 C8 115.1(4) . . ? C17 C7 C8 111.5(4) . . ? N1 C8 C18 105.4(4) . . ? N1 C8 C7 105.1(3) . . ? C18 C8 C7 117.5(4) . . ? N1 C8 H8 109.5 . . ? C18 C8 H8 109.5 . . ? C7 C8 H8 109.5 . . ? O4 C9 N1 122.9(5) . . ? O4 C9 C10 122.7(4) . . ? N1 C9 C10 114.3(4) . . ? C9 C10 C11 116.3(4) . . ? C9 C10 H10A 108.2 . . ? C11 C10 H10A 108.2 . . ? C9 C10 H10B 108.2 . . ? C11 C10 H10B 108.2 . . ? H10A C10 H10B 107.4 . . ? O1 C11 C18 114.6(4) . . ? O1 C11 C10 106.0(4) . . ? C18 C11 C10 109.9(4) . . ? O1 C11 H11 108.7 . . ? C18 C11 H11 108.7 . . ? C10 C11 H11 108.7 . . ? O1 C12 C13 109.7(4) . . ? O1 C12 H12A 109.7 . . ? C13 C12 H12A 109.7 . . ? O1 C12 H12B 109.7 . . ? C13 C12 H12B 109.7 . . ? H12A C12 H12B 108.2 . . ? C14 C13 C12 121.4(5) . . ? C14 C13 H3 119.3 . . ? C12 C13 H3 119.3 . . ? C13 C14 C15 121.7(4) . . ? C13 C14 C19 123.1(5) . . ? C15 C14 C19 115.3(4) . . ? C14 C15 N2 110.3(4) . . ? C14 C15 H15A 109.6 . . ? N2 C15 H15A 109.6 . . ? C14 C15 H15B 109.6 . . ? N2 C15 H15B 109.6 . . ? H15A C15 H15B 108.1 . . ? N2 C16 C17 103.9(4) . . ? N2 C16 H16A 111.0 . . ? C17 C16 H16A 111.0 . . ? N2 C16 H16B 111.0 . . ? C17 C16 H16B 111.0 . . ? H16A C16 H16B 109.0 . . ? C16 C17 C7 102.9(4) . . ? C16 C17 H17A 111.2 . . ? C7 C17 H17A 111.2 . . ? C16 C17 H17B 111.2 . . ? C7 C17 H17B 111.2 . . ? H17A C17 H17B 109.1 . . ? C8 C18 C11 106.5(4) . . ? C8 C18 C19 112.7(4) . . ? C11 C18 C19 119.4(4) . . ? C8 C18 H18 105.7 . . ? C11 C18 H18 105.7 . . ? C19 C18 H18 105.7 . . ? C14 C19 C20 109.7(4) . . ? C14 C19 C18 113.9(4) . . ? C20 C19 C18 106.2(3) . . ? C14 C19 H19 109.0 . . ? C20 C19 H19 109.0 . . ? C18 C19 H19 109.0 . . ? C21 C20 C19 109.0(4) . . ? 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 115.6(4) . . ? C20 C21 N2 110.0(4) . . ? C7 C21 N2 104.4(4) . . ? C20 C21 H21 108.9 . . ? C7 C21 H21 108.9 . . ? N2 C21 H21 108.9 . . ? 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 . . ? H41W O4W H42W 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 C28 N3 C25 C26 72.5(6) . . . . ? C28 N3 C25 C24 -54.9(6) . . . . ? O5 C24 C25 N3 -45.9(6) . . . . ? O6 C24 C25 N3 138.3(5) . . . . ? O5 C24 C25 C26 -172.2(4) . . . . ? O6 C24 C25 C26 12.1(6) . . . . ? N3 C25 C26 C27 50.8(6) . . . . ? C24 C25 C26 C27 176.9(4) . . . . ? C25 C26 C27 O7 43.8(6) . . . . ? C25 C26 C27 N4 -134.9(5) . . . . ? C25 N3 C28 O8 6.9(7) . . . . ? C25 N3 C28 C29 -172.1(4) . . . . ? O8 C28 C29 C34 -149.7(5) . . . . ? N3 C28 C29 C34 29.4(7) . . . . ? O8 C28 C29 C3O 26.8(7) . . . . ? N3 C28 C29 C3O -154.1(4) . . . . ? C34 C29 C3O C31 -0.6(7) . . . . ? C28 C29 C3O C31 -177.2(4) . . . . ? C29 C3O C31 C32 0.3(7) . . . . ? C3O C31 C32 C33 0.2(8) . . . . ? C3O C31 C32 N5 178.7(4) . . . . ? O10 N5 C32 C33 168.3(5) . . . . ? O9 N5 C32 C33 -11.3(7) . . . . ? O10 N5 C32 C31 -10.3(7) . . . . ? O9 N5 C32 C31 170.2(5) . . . . ? C31 C32 C33 C34 -0.4(8) . . . . ? N5 C32 C33 C34 -178.9(4) . . . . ? C3O C29 C34 C33 0.4(7) . . . . ? C28 C29 C34 C33 176.9(4) . . . . ? C32 C33 C34 C29 0.1(7) . . . . ? C22 O2 C2 C1 7.9(7) . . . . ? C22 O2 C2 C3 -171.5(4) . . . . ? C6 C1 C2 O2 -178.3(5) . . . . ? C6 C1 C2 C3 1.1(7) . . . . ? C23 O3 C3 C4 -4.1(7) . . . . ? C23 O3 C3 C2 175.1(4) . . . . ? O2 C2 C3 O3 -3.2(7) . . . . ? C1 C2 C3 O3 177.5(4) . . . . ? O2 C2 C3 C4 176.1(4) . . . . ? C1 C2 C3 C4 -3.3(8) . . . . ? O3 C3 C4 C5 -178.2(4) . . . . ? C2 C3 C4 C5 2.6(7) . . . . ? C3 C4 C5 C6 0.1(7) . . . . ? C3 C4 C5 C7 -173.0(5) . . . . ? C4 C5 C6 C1 -2.3(7) . . . . ? C7 C5 C6 C1 171.9(4) . . . . ? C4 C5 C6 N1 -179.9(4) . . . . ? C7 C5 C6 N1 -5.7(6) . . . . ? C2 C1 C6 C5 1.7(7) . . . . ? C2 C1 C6 N1 178.8(5) . . . . ? C9 N1 C6 C5 -158.0(4) . . . . ? C8 N1 C6 C5 -5.0(5) . . . . ? C9 N1 C6 C1 24.6(8) . . . . ? C8 N1 C6 C1 177.6(5) . . . . ? C6 C5 C7 C21 138.5(4) . . . . ? C4 C5 C7 C21 -47.9(7) . . . . ? C6 C5 C7 C17 -106.0(5) . . . . ? C4 C5 C7 C17 67.6(6) . . . . ? C6 C5 C7 C8 13.4(5) . . . . ? C4 C5 C7 C8 -173.0(5) . . . . ? C9 N1 C8 C18 43.7(5) . . . . ? C6 N1 C8 C18 -111.7(4) . . . . ? C9 N1 C8 C7 168.5(4) . . . . ? C6 N1 C8 C7 13.1(5) . . . . ? C5 C7 C8 N1 -15.3(5) . . . . ? C21 C7 C8 N1 -139.9(4) . . . . ? C17 C7 C8 N1 104.1(4) . . . . ? C5 C7 C8 C18 101.5(4) . . . . ? C21 C7 C8 C18 -23.1(6) . . . . ? C17 C7 C8 C18 -139.1(4) . . . . ? C6 N1 C9 O4 -17.6(7) . . . . ? C8 N1 C9 O4 -168.5(4) . . . . ? C6 N1 C9 C10 164.6(4) . . . . ? C8 N1 C9 C10 13.7(6) . . . . ? O4 C9 C10 C11 137.2(5) . . . . ? N1 C9 C10 C11 -44.9(6) . . . . ? C12 O1 C11 C18 -66.5(5) . . . . ? C12 O1 C11 C10 172.2(4) . . . . ? C9 C10 C11 O1 137.7(4) . . . . ? C9 C10 C11 C18 13.3(6) . . . . ? C11 O1 C12 C13 91.0(5) . . . . ? O1 C12 C13 C14 -67.6(6) . . . . ? C12 C13 C14 C15 177.9(4) . . . . ? C12 C13 C14 C19 -2.7(7) . . . . ? C13 C14 C15 N2 -126.7(5) . . . . ? C19 C14 C15 N2 54.0(5) . . . . ? C16 N2 C15 C14 75.1(5) . . . . ? C21 N2 C15 C14 -46.5(5) . . . . ? C15 N2 C16 C17 -142.8(4) . . . . ? C21 N2 C16 C17 -17.8(5) . . . . ? N2 C16 C17 C7 38.1(5) . . . . ? C5 C7 C17 C16 -166.7(4) . . . . ? C21 C7 C17 C16 -44.0(4) . . . . ? C8 C7 C17 C16 79.5(4) . . . . ? N1 C8 C18 C11 -72.5(4) . . . . ? C7 C8 C18 C11 170.8(4) . . . . ? N1 C8 C18 C19 154.6(4) . . . . ? C7 C8 C18 C19 38.0(5) . . . . ? O1 C11 C18 C8 -76.4(4) . . . . ? C10 C11 C18 C8 42.8(5) . . . . ? O1 C11 C18 C19 52.7(6) . . . . ? C10 C11 C18 C19 171.8(4) . . . . ? C13 C14 C19 C20 178.0(4) . . . . ? C15 C14 C19 C20 -2.6(5) . . . . ? C13 C14 C19 C18 59.1(6) . . . . ? C15 C14 C19 C18 -121.5(4) . . . . ? C8 C18 C19 C14 61.4(5) . . . . ? C11 C18 C19 C14 -64.8(6) . . . . ? C8 C18 C19 C20 -59.5(5) . . . . ? C11 C18 C19 C20 174.4(4) . . . . ? C14 C19 C20 C21 -55.3(5) . . . . ? C18 C19 C20 C21 68.2(5) . . . . ? C19 C20 C21 C7 -56.1(5) . . . . ? C19 C20 C21 N2 61.9(5) . . . . ? C5 C7 C21 C20 -85.8(5) . . . . ? C17 C7 C21 C20 153.4(4) . . . . ? C8 C7 C21 C20 32.3(5) . . . . ? C5 C7 C21 N2 153.2(4) . . . . ? C17 C7 C21 N2 32.4(4) . . . . ? C8 C7 C21 N2 -88.7(4) . . . . ? C15 N2 C21 C20 -9.8(5) . . . . ? C16 N2 C21 C20 -133.9(4) . . . . ? C15 N2 C21 C7 114.8(4) . . . . ? C16 N2 C21 C7 -9.3(4) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H24 O7W 0.93 1.99 2.840(5) 150.8 . N3 H37 O6W 0.88 2.12 2.944(5) 154.7 . N4 H471 O6W 0.88 2.09 2.951(6) 164.3 1_655 N4 H472 O5 0.88 2.06 2.826(6) 144.6 1_655 O1W H11W O3W 0.88 1.92 2.789(6) 170.6 . O1W H12W O5W 0.87 2.05 2.834(5) 150.7 . O2W H21W O7W 0.88 1.93 2.784(5) 163.9 . O2W H22W O1W 0.87 1.99 2.832(6) 163.1 . O3W H31W O7 0.88 1.93 2.758(5) 154.9 . O3W H32W O5 0.88 2.07 2.956(6) 176.1 3_655 O4W H41W O4 0.87 1.98 2.849(5) 175.6 . O4W H42W O1 0.87 2.09 2.930(5) 164.4 4_465 O5W H51W O6 0.87 1.87 2.738(5) 174.5 1_565 O5W H52W O7 0.87 2.08 2.854(5) 147.5 3_755 O6W H61W O6 0.87 1.98 2.829(5) 168.3 3_655 O6W H62W O2W 0.87 1.92 2.781(5) 169.9 . O7W H71W O7 0.87 1.89 2.760(5) 175.4 3_655 O7W H72W O6 0.85 1.90 2.716(5) 160.3 1_565 _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.508 _refine_diff_density_min -0.413 _refine_diff_density_rms 0.068 #===== end data_1a _database_code_depnum_ccdc_archive 'CCDC 783802' #TrackingRef '- bialonska_cif.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; brucinium N-(4-nitrobenzoyl)-D-asparaginate methanol disolvate 0.73-hydrate ; _chemical_name_common ;brucinium N-(4-nitrobenzoyl)-D-asparaginate methanol disolvate 0.73-hydrate ; _chemical_melting_point ? _chemical_formula_moiety ; C23 H27 N2 O4, C11 H10 N3 O6, 2(C H4 O), 0.73(H2 O) ; _chemical_formula_sum 'C36 H46.45 N5 O12.73' _chemical_formula_weight 752.87 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 7.979(2) _cell_length_b 19.404(3) _cell_length_c 22.853(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3538.2(12) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 18256 _cell_measurement_theta_min 3.11 _cell_measurement_theta_max 28.50 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.413 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1597 _exptl_absorpt_coefficient_mu 0.108 _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 23757 _diffrn_reflns_av_R_equivalents 0.0444 _diffrn_reflns_av_sigmaI/netI 0.0464 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 3.11 _diffrn_reflns_theta_max 27.50 _reflns_number_total 4548 _reflns_number_gt 3682 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.31.8 (release 12-01-2007 CrysAlis171 .NET) (compiled Jan 12 2007,17:49:11) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.8 (release 12-01-2007 CrysAlis171 .NET) (compiled Jan 12 2007,17:49:11) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.8 (release 12-01-2007 CrysAlis171 .NET) (compiled Jan 12 2007,17:49:11) ; _computing_structure_solution ; SHELXS-97 (Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.) ; _computing_structure_refinement ; SHELXL-97 (Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.) ; _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0519P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _chemical_absolute_configuration rm _refine_ls_abs_structure_details 'from known structure (Toda et al., 1985)' _refine_ls_number_reflns 4548 _refine_ls_number_parameters 520 _refine_ls_number_restraints 12 _refine_ls_R_factor_all 0.0655 _refine_ls_R_factor_gt 0.0462 _refine_ls_wR_factor_ref 0.0970 _refine_ls_wR_factor_gt 0.0921 _refine_ls_goodness_of_fit_ref 1.078 _refine_ls_restrained_S_all 1.077 _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 0.3061(3) 0.10396(10) 0.42750(8) 0.0266(5) Uani 1 1 d . . . O2 O 0.3291(3) 0.55286(10) 0.45792(8) 0.0251(5) Uani 1 1 d . . . O3 O 0.2794(3) 0.56063(10) 0.34672(8) 0.0266(5) Uani 1 1 d . . . O4 O 0.3024(3) 0.30910(10) 0.53637(9) 0.0301(5) Uani 1 1 d . . . N1 N 0.3579(3) 0.29830(11) 0.43904(10) 0.0201(5) Uani 1 1 d . . . N2 N 0.2967(3) 0.23424(11) 0.24455(10) 0.0227(5) Uani 1 1 d . . . H24 H 0.2919 0.2521 0.2068 0.027 Uiso 1 1 calc R . . C1 C 0.3442(3) 0.42715(14) 0.45645(12) 0.0210(6) Uani 1 1 d . . . H1 H 0.3609 0.4240 0.4975 0.025 Uiso 1 1 calc R . . C2 C 0.3250(4) 0.49059(14) 0.42902(12) 0.0220(6) Uani 1 1 d . . . C3 C 0.2986(4) 0.49526(14) 0.36860(12) 0.0211(6) Uani 1 1 d . . . C4 C 0.2942(4) 0.43580(14) 0.33450(12) 0.0213(6) Uani 1 1 d . . . H4 H 0.2772 0.4386 0.2934 0.026 Uiso 1 1 calc R . . C5 C 0.3152(4) 0.37226(14) 0.36159(12) 0.0207(6) Uani 1 1 d . . . C6 C 0.3380(3) 0.36869(14) 0.42176(12) 0.0210(6) Uani 1 1 d . . . C7 C 0.3350(4) 0.30238(13) 0.33334(11) 0.0189(6) Uani 1 1 d . . . C8 C 0.3327(4) 0.25283(13) 0.38705(11) 0.0194(6) Uani 1 1 d . . . H8 H 0.4280 0.2195 0.3840 0.023 Uiso 1 1 calc R . . C9 C 0.3204(4) 0.27244(14) 0.49289(13) 0.0246(7) Uani 1 1 d . . . C10 C 0.3104(4) 0.19451(14) 0.49560(12) 0.0268(7) Uani 1 1 d . . . H10A H 0.2617 0.1812 0.5338 0.032 Uiso 1 1 calc R . . H10B H 0.4258 0.1758 0.4941 0.032 Uiso 1 1 calc R . . C11 C 0.2063(4) 0.16032(14) 0.44660(12) 0.0241(7) Uani 1 1 d . . . H11 H 0.0984 0.1428 0.4631 0.029 Uiso 1 1 calc R . . C12 C 0.2239(4) 0.05775(15) 0.38696(13) 0.0302(7) Uani 1 1 d . . . H12A H 0.1029 0.0555 0.3964 0.036 Uiso 1 1 calc R . . H12B H 0.2712 0.0109 0.3914 0.036 Uiso 1 1 calc R . . C13 C 0.2455(4) 0.08102(15) 0.32467(13) 0.0280(7) Uani 1 1 d . . . H13 H 0.3051 0.0520 0.2984 0.034 Uiso 1 1 calc R . . C14 C 0.1851(4) 0.14008(14) 0.30466(12) 0.0247(7) Uani 1 1 d . . . C15 C 0.2176(4) 0.16414(14) 0.24353(12) 0.0264(7) Uani 1 1 d . . . H15A H 0.1108 0.1660 0.2215 0.032 Uiso 1 1 calc R . . H15B H 0.2931 0.1312 0.2235 0.032 Uiso 1 1 calc R . . C16 C 0.4777(4) 0.23230(15) 0.26283(13) 0.0253(7) Uani 1 1 d . . . H16A H 0.5522 0.2329 0.2282 0.030 Uiso 1 1 calc R . . H16B H 0.5016 0.1904 0.2861 0.030 Uiso 1 1 calc R . . C17 C 0.5021(4) 0.29618(15) 0.29930(13) 0.0249(7) Uani 1 1 d . . . H17A H 0.5211 0.3371 0.2743 0.030 Uiso 1 1 calc R . . H17B H 0.5981 0.2909 0.3264 0.030 Uiso 1 1 calc R . . C18 C 0.1699(4) 0.21351(14) 0.39868(11) 0.0201(6) Uani 1 1 d . . . H18 H 0.0920 0.2477 0.4168 0.024 Uiso 1 1 calc R . . C19 C 0.0822(4) 0.18923(14) 0.34206(13) 0.0223(7) Uani 1 1 d . . . H19 H -0.0257 0.1662 0.3527 0.027 Uiso 1 1 calc R . . C20 C 0.0435(4) 0.25429(15) 0.30685(12) 0.0225(7) Uani 1 1 d . . . H20A H -0.0286 0.2427 0.2730 0.027 Uiso 1 1 calc R . . H20B H -0.0170 0.2879 0.3317 0.027 Uiso 1 1 calc R . . C21 C 0.2063(4) 0.28521(14) 0.28573(12) 0.0215(6) Uani 1 1 d . . . H21 H 0.1807 0.3282 0.2634 0.026 Uiso 1 1 calc R . . C22 C 0.3752(4) 0.55292(16) 0.51845(12) 0.0287(7) Uani 1 1 d . . . H22A H 0.3726 0.6002 0.5335 0.043 Uiso 1 1 calc R . . H22B H 0.4886 0.5341 0.5227 0.043 Uiso 1 1 calc R . . H22C H 0.2961 0.5245 0.5406 0.043 Uiso 1 1 calc R . . C23 C 0.2447(5) 0.56549(16) 0.28522(13) 0.0358(8) Uani 1 1 d . . . H23A H 0.2344 0.6141 0.2741 0.054 Uiso 1 1 calc R . . H23B H 0.1396 0.5415 0.2765 0.054 Uiso 1 1 calc R . . H23C H 0.3363 0.5442 0.2631 0.054 Uiso 1 1 calc R . . O5 O 0.2774(2) 0.24866(10) 0.12858(8) 0.0235(5) Uani 1 1 d . . . O6 O 0.3061(2) 0.26815(10) 0.03292(8) 0.0207(4) Uani 1 1 d . . . O7 O 0.8369(3) 0.23274(10) 0.17564(8) 0.0250(5) Uani 1 1 d . . . O8 O 0.4997(3) 0.41896(10) 0.08265(8) 0.0266(5) Uani 1 1 d . . . O9 O 0.6984(4) 0.59784(12) -0.16669(12) 0.0561(8) Uani 1 1 d . . . O10 O 0.8350(3) 0.51029(11) -0.20066(9) 0.0351(5) Uani 1 1 d . . . N3 N 0.6210(3) 0.32237(11) 0.04835(11) 0.0184(5) Uani 1 1 d . . . H3 H 0.672(4) 0.2995(15) 0.0150(14) 0.033(9) Uiso 1 1 d . . . N4 N 0.9414(3) 0.21926(13) 0.08503(11) 0.0251(6) Uani 1 1 d . . . H4A H 1.0450 0.2259 0.0970 0.030 Uiso 1 1 calc R . . H4B H 0.9210 0.2111 0.0478 0.030 Uiso 1 1 calc R . . N5 N 0.7527(3) 0.53897(13) -0.16262(12) 0.0306(7) Uani 1 1 d . . . C24 C 0.3613(3) 0.26597(13) 0.08410(12) 0.0167(6) Uani 1 1 d . . . C25 C 0.5489(3) 0.28040(14) 0.09476(12) 0.0171(6) Uani 1 1 d . . . H25 H 0.5616 0.3052 0.1328 0.021 Uiso 1 1 calc R . . C26 C 0.6410(3) 0.21120(14) 0.09857(12) 0.0177(6) Uani 1 1 d . . . H26A H 0.5777 0.1794 0.1242 0.021 Uiso 1 1 calc R . . H26B H 0.6480 0.1902 0.0592 0.021 Uiso 1 1 calc R . . C27 C 0.8166(4) 0.22153(13) 0.12295(12) 0.0179(6) Uani 1 1 d . . . C28 C 0.5807(3) 0.38939(14) 0.04440(13) 0.0195(6) Uani 1 1 d . . . C29 C 0.6370(3) 0.42783(14) -0.00926(12) 0.0193(6) Uani 1 1 d . . . C30 C 0.5604(4) 0.49094(14) -0.02030(13) 0.0227(6) Uani 1 1 d . . . H30 H 0.4818 0.5088 0.0070 0.027 Uiso 1 1 calc R . . C31 C 0.5966(4) 0.52789(15) -0.07001(13) 0.0237(7) Uani 1 1 d . . . H31 H 0.5431 0.5707 -0.0777 0.028 Uiso 1 1 calc R . . C32 C 0.7133(4) 0.50088(14) -0.10846(12) 0.0222(6) Uani 1 1 d . . . C33 C 0.7977(4) 0.43956(14) -0.09819(12) 0.0239(6) Uani 1 1 d . . . H33 H 0.8801 0.4231 -0.1247 0.029 Uiso 1 1 calc R . . C34 C 0.7577(4) 0.40312(15) -0.04782(13) 0.0230(7) Uani 1 1 d . . . H34 H 0.8132 0.3609 -0.0396 0.028 Uiso 1 1 calc R . . O1W O 0.2999(15) 0.4072(5) 0.1857(5) 0.054(3) Uani 0.727(7) 1 d P A 1 H11W H 0.2142 0.3945 0.1786 0.081 Uiso 0.727(7) 1 d PR A 1 H12W H 0.3669 0.4056 0.1521 0.081 Uiso 0.727(7) 1 d PR A 1 O35 O -0.0018(4) 0.35890(18) 0.1775(2) 0.0624(15) Uani 0.727(7) 1 d P A 1 H35 H -0.0562 0.3165 0.1769 0.094 Uiso 0.727(7) 1 d PR A 1 C35 C -0.1277(7) 0.4039(3) 0.1860(3) 0.061(2) Uani 0.727(7) 1 d P A 1 H35A H -0.2111 0.3836 0.2123 0.091 Uiso 0.727(7) 1 calc PR A 1 H35B H -0.1805 0.4147 0.1483 0.091 Uiso 0.727(7) 1 calc PR A 1 H35C H -0.0833 0.4463 0.2034 0.091 Uiso 0.727(7) 1 calc PR A 1 O351 O 0.300(2) 0.4224(14) 0.1816(13) 0.028(4) Uani 0.273(7) 1 d PU A 2 H351 H 0.3625 0.4068 0.1550 0.042 Uiso 0.273(7) 1 calc PR A 2 C351 C 0.1046(19) 0.4041(8) 0.1664(6) 0.044(4) Uani 0.273(7) 1 d PU A 2 H35D H 0.0886 0.4043 0.1239 0.066 Uiso 0.273(7) 1 calc PR A 2 H35E H 0.0312 0.4388 0.1842 0.066 Uiso 0.273(7) 1 calc PR A 2 H35F H 0.0768 0.3585 0.1820 0.066 Uiso 0.273(7) 1 calc PR A 2 O36 O 0.3219(6) 0.6475(3) 0.14239(19) 0.0429(16) Uani 0.495(6) 1 d P B 1 H36 H 0.2852 0.6686 0.1129 0.064 Uiso 0.495(6) 1 calc PR B 1 O361 O 0.1824(6) 0.5461(2) 0.14890(19) 0.0392(15) Uani 0.505(6) 1 d P B 2 H361 H 0.2046 0.5059 0.1600 0.059 Uiso 0.505(6) 1 calc PR B 2 C36 C 0.3246(5) 0.57763(18) 0.13108(15) 0.0387(8) Uani 1 1 d . . . H36A H 0.3401 0.5523 0.1678 0.058 Uiso 0.495(6) 1 calc PR B 1 H36B H 0.4173 0.5671 0.1044 0.058 Uiso 0.495(6) 1 calc PR B 1 H36C H 0.2184 0.5638 0.1130 0.058 Uiso 0.495(6) 1 calc PR B 1 H36D H 0.3668 0.5547 0.0958 0.058 Uiso 0.505(6) 1 d PR B 2 H36E H 0.4091 0.5748 0.1621 0.058 Uiso 0.505(6) 1 d PR B 2 H36F H 0.3011 0.6261 0.1223 0.058 Uiso 0.505(6) 1 d PR B 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 0.0371(12) 0.0182(10) 0.0246(11) 0.0001(8) -0.0021(10) 0.0013(10) O2 0.0351(12) 0.0191(10) 0.0211(10) -0.0038(8) -0.0040(10) -0.0010(9) O3 0.0403(13) 0.0173(10) 0.0220(10) 0.0026(9) -0.0040(10) -0.0020(10) O4 0.0416(13) 0.0278(11) 0.0208(11) -0.0019(9) -0.0006(11) 0.0001(11) N1 0.0257(13) 0.0163(12) 0.0184(12) 0.0002(9) 0.0017(10) 0.0008(11) N2 0.0314(14) 0.0199(12) 0.0169(12) 0.0014(10) 0.0029(11) -0.0017(12) C1 0.0234(15) 0.0228(15) 0.0168(14) -0.0004(12) -0.0016(12) 0.0006(13) C2 0.0212(15) 0.0204(15) 0.0245(15) -0.0025(12) 0.0013(13) -0.0005(13) C3 0.0230(15) 0.0155(14) 0.0249(15) 0.0025(11) 0.0015(13) -0.0020(13) C4 0.0261(15) 0.0204(14) 0.0174(14) 0.0001(11) 0.0004(12) -0.0017(13) C5 0.0206(15) 0.0183(14) 0.0233(15) -0.0018(11) 0.0030(13) -0.0035(13) C6 0.0178(15) 0.0188(14) 0.0265(16) 0.0010(12) 0.0023(13) -0.0004(12) C7 0.0223(15) 0.0164(14) 0.0181(14) 0.0011(11) 0.0029(12) -0.0003(12) C8 0.0241(15) 0.0146(14) 0.0193(14) 0.0000(11) 0.0004(13) -0.0005(12) C9 0.0247(17) 0.0241(16) 0.0250(16) 0.0025(13) -0.0033(14) -0.0004(14) C10 0.0347(18) 0.0265(16) 0.0193(15) 0.0043(12) 0.0002(14) -0.0001(15) C11 0.0289(16) 0.0202(14) 0.0231(15) 0.0019(12) 0.0046(14) -0.0011(13) C12 0.043(2) 0.0188(15) 0.0290(17) 0.0007(13) -0.0025(15) -0.0035(15) C13 0.0378(19) 0.0194(15) 0.0268(17) -0.0029(13) 0.0062(14) -0.0019(14) C14 0.0280(16) 0.0211(15) 0.0249(16) -0.0020(12) -0.0021(14) -0.0069(14) C15 0.0389(18) 0.0172(14) 0.0230(15) -0.0035(12) 0.0002(15) -0.0057(14) C16 0.0278(17) 0.0265(17) 0.0217(15) 0.0009(13) 0.0051(13) -0.0006(14) C17 0.0288(16) 0.0212(16) 0.0245(16) 0.0017(13) 0.0053(14) -0.0009(14) C18 0.0246(16) 0.0169(14) 0.0188(14) 0.0010(11) 0.0029(13) -0.0007(12) C19 0.0234(16) 0.0186(15) 0.0249(16) 0.0002(12) 0.0014(13) -0.0074(12) C20 0.0246(15) 0.0208(15) 0.0221(15) 0.0001(12) -0.0033(13) 0.0006(13) C21 0.0276(16) 0.0182(14) 0.0187(14) -0.0015(11) 0.0015(13) 0.0020(13) C22 0.0342(18) 0.0286(17) 0.0233(16) -0.0021(14) -0.0031(14) -0.0022(15) C23 0.056(2) 0.0241(17) 0.0270(17) 0.0036(14) -0.0080(16) 0.0042(17) O5 0.0173(10) 0.0331(12) 0.0200(10) 0.0037(9) 0.0028(8) -0.0034(9) O6 0.0186(10) 0.0257(10) 0.0177(10) 0.0022(8) -0.0020(8) -0.0032(9) O7 0.0242(11) 0.0299(11) 0.0210(11) -0.0023(9) -0.0026(9) 0.0017(10) O8 0.0342(13) 0.0235(11) 0.0221(11) -0.0012(9) 0.0069(10) 0.0029(10) O9 0.0628(18) 0.0332(14) 0.0723(19) 0.0288(13) 0.0341(16) 0.0137(14) O10 0.0409(13) 0.0356(13) 0.0289(12) 0.0030(10) 0.0064(11) -0.0020(11) N3 0.0185(12) 0.0160(12) 0.0206(13) 0.0011(10) 0.0020(11) -0.0018(10) N4 0.0145(12) 0.0383(15) 0.0225(13) 0.0018(11) -0.0035(11) -0.0005(11) N5 0.0305(16) 0.0251(15) 0.0362(16) 0.0061(12) 0.0044(13) -0.0035(12) C24 0.0179(14) 0.0131(13) 0.0190(14) -0.0011(11) -0.0003(12) 0.0001(12) C25 0.0179(14) 0.0188(14) 0.0148(14) 0.0002(11) 0.0006(11) -0.0009(12) C26 0.0171(14) 0.0185(14) 0.0176(14) -0.0020(11) 0.0014(12) -0.0004(12) C27 0.0186(14) 0.0130(14) 0.0220(15) 0.0019(11) -0.0035(13) 0.0029(12) C28 0.0162(14) 0.0200(15) 0.0224(16) -0.0033(12) -0.0010(13) -0.0013(12) C29 0.0178(15) 0.0168(14) 0.0233(15) -0.0024(12) -0.0038(12) -0.0049(12) C30 0.0231(15) 0.0200(15) 0.0249(16) -0.0009(13) 0.0047(13) 0.0003(13) C31 0.0218(15) 0.0159(14) 0.0333(18) 0.0027(13) 0.0020(14) 0.0006(12) C32 0.0249(15) 0.0187(14) 0.0230(15) 0.0045(12) 0.0008(13) -0.0051(13) C33 0.0251(16) 0.0214(15) 0.0250(15) -0.0033(12) 0.0029(13) -0.0002(14) C34 0.0241(16) 0.0195(14) 0.0255(16) -0.0008(12) 0.0000(13) 0.0007(12) O1W 0.093(5) 0.039(5) 0.030(3) 0.001(3) 0.018(3) -0.009(3) O35 0.028(2) 0.036(2) 0.124(4) -0.020(2) -0.002(2) -0.0010(17) C35 0.051(4) 0.026(3) 0.106(5) -0.001(3) 0.000(4) 0.010(3) O351 0.019(6) 0.036(9) 0.029(7) 0.000(6) 0.000(5) -0.002(5) C351 0.059(8) 0.046(7) 0.028(6) 0.006(5) 0.008(6) 0.008(6) O36 0.047(3) 0.052(3) 0.029(3) -0.008(2) -0.007(2) -0.002(3) O361 0.033(3) 0.047(3) 0.038(3) -0.002(2) 0.002(2) 0.002(2) C36 0.039(2) 0.041(2) 0.0367(19) 0.0001(16) -0.0018(17) -0.0043(18) _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 1.422(3) . ? O1 C12 1.447(3) . ? O2 C2 1.377(3) . ? O2 C22 1.432(3) . ? O3 C3 1.372(3) . ? O3 C23 1.436(3) . ? O4 C9 1.230(3) . ? N1 C9 1.362(4) . ? N1 C6 1.431(3) . ? N1 C8 1.494(3) . ? N2 C15 1.500(4) . ? N2 C16 1.504(4) . ? N2 C21 1.544(3) . ? N2 H24 0.9300 . ? C1 C6 1.385(4) . ? C1 C2 1.390(4) . ? C1 H1 0.9500 . ? C2 C3 1.400(4) . ? C3 C4 1.393(4) . ? C4 C5 1.390(4) . ? C4 H4 0.9500 . ? C5 C6 1.389(4) . ? C5 C7 1.510(4) . ? C7 C21 1.533(4) . ? C7 C17 1.548(4) . ? C7 C8 1.559(4) . ? C8 C18 1.530(4) . ? C8 H8 1.0000 . ? C9 C10 1.516(4) . ? C10 C11 1.544(4) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C18 1.533(4) . ? C11 H11 1.0000 . ? C12 C13 1.503(4) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.324(4) . ? C13 H13 0.9500 . ? C14 C15 1.496(4) . ? C14 C19 1.521(4) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 C17 1.506(4) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 C19 1.545(4) . ? C18 H18 1.0000 . ? C19 C20 1.529(4) . ? C19 H19 1.0000 . ? C20 C21 1.511(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 1.263(3) . ? O6 C24 1.250(3) . ? O7 C27 1.234(3) . ? O8 C28 1.230(3) . ? O9 N5 1.225(3) . ? O10 N5 1.224(3) . ? N3 C28 1.343(3) . ? N3 C25 1.456(3) . ? N3 H3 0.97(3) . ? N4 C27 1.321(4) . ? N4 H4A 0.8800 . ? N4 H4B 0.8800 . ? N5 C32 1.475(4) . ? C24 C25 1.542(4) . ? C25 C26 1.533(4) . ? C25 H25 1.0000 . ? C26 C27 1.521(4) . ? C26 H26A 0.9900 . ? C26 H26B 0.9900 . ? C28 C29 1.504(4) . ? C29 C34 1.391(4) . ? C29 C30 1.392(4) . ? C30 C31 1.374(4) . ? C30 H30 0.9500 . ? C31 C32 1.384(4) . ? C31 H31 0.9500 . ? C32 C33 1.387(4) . ? C33 C34 1.388(4) . ? C33 H33 0.9500 . ? C34 H34 0.9500 . ? O1W H11W 0.7450 . ? O1W H12W 0.9358 . ? O35 C35 1.346(6) . ? O35 H35 0.9300 . ? C35 H35A 0.9800 . ? C35 H35B 0.9800 . ? C35 H35C 0.9800 . ? O351 C351 1.64(3) . ? O351 H11W 0.8763 . ? O351 H12W 0.9176 . ? O351 H351 0.8400 . ? C351 H11W 0.9372 . ? C351 H35D 0.9800 . ? C351 H35E 0.9800 . ? C351 H35F 0.9800 . ? O36 C36 1.381(6) . ? O36 H36 0.8400 . ? O36 H36F 0.6415 . ? O361 C36 1.352(6) . ? O361 H361 0.8400 . ? C36 H36A 0.9800 . ? C36 H36B 0.9800 . ? C36 H36C 0.9800 . ? C36 H36D 0.9798 . ? C36 H36E 0.9802 . ? C36 H36F 0.9799 . ? 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 114.8(2) . . ? C2 O2 C22 118.0(2) . . ? C3 O3 C23 116.0(2) . . ? C9 N1 C6 125.2(2) . . ? C9 N1 C8 118.1(2) . . ? C6 N1 C8 109.2(2) . . ? C15 N2 C16 112.7(2) . . ? C15 N2 C21 113.2(2) . . ? C16 N2 C21 107.2(2) . . ? C15 N2 H24 107.9 . . ? C16 N2 H24 107.9 . . ? C21 N2 H24 107.9 . . ? C6 C1 C2 117.6(3) . . ? C6 C1 H1 121.2 . . ? C2 C1 H1 121.2 . . ? O2 C2 C1 123.9(2) . . ? O2 C2 C3 114.8(2) . . ? C1 C2 C3 121.3(3) . . ? O3 C3 C4 124.0(2) . . ? O3 C3 C2 115.9(2) . . ? C4 C3 C2 120.1(3) . . ? C5 C4 C3 118.9(2) . . ? C5 C4 H4 120.6 . . ? C3 C4 H4 120.6 . . ? C6 C5 C4 120.1(2) . . ? C6 C5 C7 111.4(2) . . ? C4 C5 C7 128.2(2) . . ? C1 C6 C5 122.0(3) . . ? C1 C6 N1 128.3(3) . . ? C5 C6 N1 109.6(2) . . ? C5 C7 C21 115.4(2) . . ? C5 C7 C17 112.0(2) . . ? C21 C7 C17 101.7(2) . . ? C5 C7 C8 102.5(2) . . ? C21 C7 C8 114.6(2) . . ? C17 C7 C8 111.0(2) . . ? N1 C8 C18 105.7(2) . . ? N1 C8 C7 105.1(2) . . ? C18 C8 C7 117.0(2) . . ? N1 C8 H8 109.6 . . ? C18 C8 H8 109.6 . . ? C7 C8 H8 109.6 . . ? O4 C9 N1 122.8(3) . . ? O4 C9 C10 122.5(2) . . ? N1 C9 C10 114.6(3) . . ? C9 C10 C11 115.3(2) . . ? C9 C10 H10A 108.5 . . ? C11 C10 H10A 108.5 . . ? C9 C10 H10B 108.5 . . ? C11 C10 H10B 108.5 . . ? H10A C10 H10B 107.5 . . ? O1 C11 C18 113.9(2) . . ? O1 C11 C10 104.6(2) . . ? C18 C11 C10 109.3(2) . . ? O1 C11 H11 109.6 . . ? C18 C11 H11 109.6 . . ? C10 C11 H11 109.6 . . ? O1 C12 C13 111.6(2) . . ? 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 123.0(3) . . ? C14 C13 H13 118.5 . . ? C12 C13 H13 118.5 . . ? C13 C14 C15 122.0(3) . . ? C13 C14 C19 123.0(3) . . ? C15 C14 C19 115.0(2) . . ? C14 C15 N2 110.0(2) . . ? C14 C15 H15A 109.7 . . ? N2 C15 H15A 109.7 . . ? C14 C15 H15B 109.7 . . ? N2 C15 H15B 109.7 . . ? H15A C15 H15B 108.2 . . ? N2 C16 C17 104.9(2) . . ? N2 C16 H16A 110.8 . . ? C17 C16 H16A 110.8 . . ? N2 C16 H16B 110.8 . . ? C17 C16 H16B 110.8 . . ? H16A C16 H16B 108.8 . . ? C16 C17 C7 103.4(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 C11 107.4(2) . . ? C8 C18 C19 113.0(2) . . ? C11 C18 C19 118.6(2) . . ? C8 C18 H18 105.6 . . ? C11 C18 H18 105.6 . . ? C19 C18 H18 105.6 . . ? C14 C19 C20 109.3(2) . . ? C14 C19 C18 114.7(2) . . ? C20 C19 C18 106.3(2) . . ? C14 C19 H19 108.8 . . ? C20 C19 H19 108.8 . . ? C18 C19 H19 108.8 . . ? C21 C20 C19 108.8(2) . . ? 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 115.8(2) . . ? C20 C21 N2 110.0(2) . . ? C7 C21 N2 105.0(2) . . ? C20 C21 H21 108.6 . . ? C7 C21 H21 108.6 . . ? N2 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 . . ? C28 N3 C25 119.7(2) . . ? C28 N3 H3 119.4(18) . . ? C25 N3 H3 118.7(18) . . ? C27 N4 H4A 120.0 . . ? C27 N4 H4B 120.0 . . ? H4A N4 H4B 120.0 . . ? O10 N5 O9 124.1(3) . . ? O10 N5 C32 118.8(2) . . ? O9 N5 C32 117.1(3) . . ? O6 C24 O5 125.1(3) . . ? O6 C24 C25 118.9(2) . . ? O5 C24 C25 115.8(2) . . ? N3 C25 C26 110.0(2) . . ? N3 C25 C24 111.7(2) . . ? C26 C25 C24 108.4(2) . . ? N3 C25 H25 108.9 . . ? C26 C25 H25 108.9 . . ? C24 C25 H25 108.9 . . ? C27 C26 C25 110.3(2) . . ? C27 C26 H26A 109.6 . . ? C25 C26 H26A 109.6 . . ? C27 C26 H26B 109.6 . . ? C25 C26 H26B 109.6 . . ? H26A C26 H26B 108.1 . . ? O7 C27 N4 123.2(3) . . ? O7 C27 C26 120.1(3) . . ? N4 C27 C26 116.7(2) . . ? O8 C28 N3 122.0(3) . . ? O8 C28 C29 120.3(2) . . ? N3 C28 C29 117.6(3) . . ? C34 C29 C30 119.5(3) . . ? C34 C29 C28 123.5(3) . . ? C30 C29 C28 117.0(3) . . ? C31 C30 C29 121.1(3) . . ? C31 C30 H30 119.4 . . ? C29 C30 H30 119.4 . . ? C30 C31 C32 118.0(3) . . ? C30 C31 H31 121.0 . . ? C32 C31 H31 121.0 . . ? C31 C32 C33 123.0(3) . . ? C31 C32 N5 119.1(3) . . ? C33 C32 N5 117.9(3) . . ? C32 C33 C34 117.7(3) . . ? C32 C33 H33 121.1 . . ? C34 C33 H33 121.1 . . ? C33 C34 C29 120.6(3) . . ? C33 C34 H34 119.7 . . ? C29 C34 H34 119.7 . . ? H11W O1W H12W 109.5 . . ? C35 O35 H35 103.2 . . ? O35 C35 H35A 109.5 . . ? O35 C35 H35B 109.5 . . ? H35A C35 H35B 109.5 . . ? O35 C35 H35C 109.5 . . ? H35A C35 H35C 109.5 . . ? H35B C35 H35C 109.5 . . ? C351 O351 H11W 26.3 . . ? C351 O351 H12W 108.7 . . ? H11W O351 H12W 100.2 . . ? C351 O351 H351 109.5 . . ? H11W O351 H351 100.7 . . ? H12W O351 H351 1.0 . . ? O351 C351 H11W 24.5 . . ? O351 C351 H35D 109.5 . . ? H11W C351 H35D 114.6 . . ? O351 C351 H35E 109.5 . . ? H11W C351 H35E 124.8 . . ? H35D C351 H35E 109.5 . . ? O351 C351 H35F 109.5 . . ? H11W C351 H35F 85.5 . . ? H35D C351 H35F 109.5 . . ? H35E C351 H35F 109.5 . . ? C36 O36 H36 109.5 . . ? C36 O36 H36F 40.0 . . ? H36 O36 H36F 69.6 . . ? C36 O361 H361 109.5 . . ? O361 C36 O36 112.0(4) . . ? O361 C36 H36A 67.8 . . ? O36 C36 H36A 109.5 . . ? O361 C36 H36B 136.6 . . ? O36 C36 H36B 109.5 . . ? H36A C36 H36B 109.5 . . ? O361 C36 H36C 43.7 . . ? O36 C36 H36C 109.5 . . ? H36A C36 H36C 109.5 . . ? H36B C36 H36C 109.5 . . ? O361 C36 H36D 109.3 . . ? O36 C36 H36D 127.3 . . ? H36A C36 H36D 115.6 . . ? H36B C36 H36D 30.1 . . ? H36C C36 H36D 80.0 . . ? O361 C36 H36E 109.6 . . ? O36 C36 H36E 86.0 . . ? H36A C36 H36E 42.8 . . ? H36B C36 H36E 85.4 . . ? H36C C36 H36E 152.2 . . ? H36D C36 H36E 109.5 . . ? O361 C36 H36F 109.6 . . ? O36 C36 H36F 24.9 . . ? H36A C36 H36F 132.9 . . ? H36B C36 H36F 102.5 . . ? H36C C36 H36F 90.6 . . ? H36D C36 H36F 109.5 . . ? H36E C36 H36F 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C22 O2 C2 C1 7.7(4) . . . . ? C22 O2 C2 C3 -172.7(3) . . . . ? C6 C1 C2 O2 -179.7(3) . . . . ? C6 C1 C2 C3 0.7(4) . . . . ? C23 O3 C3 C4 3.2(4) . . . . ? C23 O3 C3 C2 -177.2(3) . . . . ? O2 C2 C3 O3 -0.4(4) . . . . ? C1 C2 C3 O3 179.2(3) . . . . ? O2 C2 C3 C4 179.1(3) . . . . ? C1 C2 C3 C4 -1.2(5) . . . . ? O3 C3 C4 C5 -180.0(3) . . . . ? C2 C3 C4 C5 0.5(5) . . . . ? C3 C4 C5 C6 0.8(5) . . . . ? C3 C4 C5 C7 -172.3(3) . . . . ? C2 C1 C6 C5 0.6(4) . . . . ? C2 C1 C6 N1 178.5(3) . . . . ? C4 C5 C6 C1 -1.3(5) . . . . ? C7 C5 C6 C1 172.8(3) . . . . ? C4 C5 C6 N1 -179.5(3) . . . . ? C7 C5 C6 N1 -5.4(3) . . . . ? C9 N1 C6 C1 28.1(5) . . . . ? C8 N1 C6 C1 177.2(3) . . . . ? C9 N1 C6 C5 -153.8(3) . . . . ? C8 N1 C6 C5 -4.7(3) . . . . ? C6 C5 C7 C21 137.8(3) . . . . ? C4 C5 C7 C21 -48.6(4) . . . . ? C6 C5 C7 C17 -106.4(3) . . . . ? C4 C5 C7 C17 67.1(4) . . . . ? C6 C5 C7 C8 12.6(3) . . . . ? C4 C5 C7 C8 -173.9(3) . . . . ? C9 N1 C8 C18 39.5(3) . . . . ? C6 N1 C8 C18 -112.0(2) . . . . ? C9 N1 C8 C7 163.9(2) . . . . ? C6 N1 C8 C7 12.3(3) . . . . ? C5 C7 C8 N1 -14.5(3) . . . . ? C21 C7 C8 N1 -140.2(2) . . . . ? C17 C7 C8 N1 105.3(3) . . . . ? C5 C7 C8 C18 102.4(3) . . . . ? C21 C7 C8 C18 -23.4(3) . . . . ? C17 C7 C8 C18 -137.9(2) . . . . ? C6 N1 C9 O4 -17.5(5) . . . . ? C8 N1 C9 O4 -164.1(3) . . . . ? C6 N1 C9 C10 165.2(3) . . . . ? C8 N1 C9 C10 18.6(4) . . . . ? O4 C9 C10 C11 135.3(3) . . . . ? N1 C9 C10 C11 -47.4(4) . . . . ? C12 O1 C11 C18 -69.1(3) . . . . ? C12 O1 C11 C10 171.6(2) . . . . ? C9 C10 C11 O1 135.0(3) . . . . ? C9 C10 C11 C18 12.7(4) . . . . ? C11 O1 C12 C13 87.9(3) . . . . ? O1 C12 C13 C14 -63.2(4) . . . . ? C12 C13 C14 C15 176.0(3) . . . . ? C12 C13 C14 C19 -2.3(5) . . . . ? C13 C14 C15 N2 -124.0(3) . . . . ? C19 C14 C15 N2 54.5(3) . . . . ? C16 N2 C15 C14 74.5(3) . . . . ? C21 N2 C15 C14 -47.4(3) . . . . ? C15 N2 C16 C17 -142.8(2) . . . . ? C21 N2 C16 C17 -17.6(3) . . . . ? N2 C16 C17 C7 37.2(3) . . . . ? C5 C7 C17 C16 -166.0(2) . . . . ? C21 C7 C17 C16 -42.3(3) . . . . ? C8 C7 C17 C16 80.1(3) . . . . ? N1 C8 C18 C11 -72.5(3) . . . . ? C7 C8 C18 C11 171.0(2) . . . . ? N1 C8 C18 C19 154.8(2) . . . . ? C7 C8 C18 C19 38.3(3) . . . . ? O1 C11 C18 C8 -72.2(3) . . . . ? C10 C11 C18 C8 44.3(3) . . . . ? O1 C11 C18 C19 57.4(4) . . . . ? C10 C11 C18 C19 174.0(2) . . . . ? C13 C14 C19 C20 176.1(3) . . . . ? C15 C14 C19 C20 -2.4(3) . . . . ? C13 C14 C19 C18 56.8(4) . . . . ? C15 C14 C19 C18 -121.7(3) . . . . ? C8 C18 C19 C14 60.9(3) . . . . ? C11 C18 C19 C14 -66.1(3) . . . . ? C8 C18 C19 C20 -60.0(3) . . . . ? C11 C18 C19 C20 172.9(3) . . . . ? C14 C19 C20 C21 -55.9(3) . . . . ? C18 C19 C20 C21 68.5(3) . . . . ? C19 C20 C21 C7 -56.5(3) . . . . ? C19 C20 C21 N2 62.4(3) . . . . ? C5 C7 C21 C20 -86.0(3) . . . . ? C17 C7 C21 C20 152.5(2) . . . . ? C8 C7 C21 C20 32.7(3) . . . . ? C5 C7 C21 N2 152.4(2) . . . . ? C17 C7 C21 N2 31.0(3) . . . . ? C8 C7 C21 N2 -88.8(3) . . . . ? C15 N2 C21 C20 -9.4(3) . . . . ? C16 N2 C21 C20 -134.3(2) . . . . ? C15 N2 C21 C7 115.9(2) . . . . ? C16 N2 C21 C7 -8.9(3) . . . . ? C28 N3 C25 C26 -167.7(2) . . . . ? C28 N3 C25 C24 71.9(3) . . . . ? O6 C24 C25 N3 24.5(3) . . . . ? O5 C24 C25 N3 -159.6(2) . . . . ? O6 C24 C25 C26 -96.9(3) . . . . ? O5 C24 C25 C26 79.1(3) . . . . ? N3 C25 C26 C27 70.8(3) . . . . ? C24 C25 C26 C27 -166.8(2) . . . . ? C25 C26 C27 O7 75.0(3) . . . . ? C25 C26 C27 N4 -103.6(3) . . . . ? C25 N3 C28 O8 8.6(4) . . . . ? C25 N3 C28 C29 -170.8(2) . . . . ? O8 C28 C29 C34 165.5(3) . . . . ? N3 C28 C29 C34 -15.0(4) . . . . ? O8 C28 C29 C30 -15.4(4) . . . . ? N3 C28 C29 C30 164.1(3) . . . . ? C34 C29 C30 C31 2.9(4) . . . . ? C28 C29 C30 C31 -176.2(3) . . . . ? C29 C30 C31 C32 -0.9(4) . . . . ? C30 C31 C32 C33 -1.8(4) . . . . ? C30 C31 C32 N5 179.1(3) . . . . ? O10 N5 C32 C31 -168.6(3) . . . . ? O9 N5 C32 C31 10.7(4) . . . . ? O10 N5 C32 C33 12.1(4) . . . . ? O9 N5 C32 C33 -168.5(3) . . . . ? C31 C32 C33 C34 2.2(4) . . . . ? N5 C32 C33 C34 -178.6(2) . . . . ? C32 C33 C34 C29 -0.1(4) . . . . ? C30 C29 C34 C33 -2.4(4) . . . . ? C28 C29 C34 C33 176.7(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 H24 O5 0.93 1.79 2.670(3) 155.9 . N3 H3 O6 0.97(3) 2.02(3) 2.952(3) 161(3) 4 N4 H4A O5 0.88 2.04 2.916(3) 175.0 1_655 N4 H4B O6 0.88 2.10 2.914(3) 153.6 4 O1W H11W O35 0.75 1.86 2.590(12) 168.0 . O1W H12W O8 0.94 1.93 2.853(12) 170.2 . O35 H35 O7 0.93 1.84 2.766(4) 179.9 1_455 O351 H351 O8 0.84 2.00 2.77(3) 151.6 . O36 H36 O4 0.84 1.93 2.750(5) 163.8 2_564 O361 H361 O351 0.84 1.86 2.69(3) 167.9 . _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.208 _refine_diff_density_min -0.168 _refine_diff_density_rms 0.042 #==== end data_2 _database_code_depnum_ccdc_archive 'CCDC 783803' #TrackingRef '- bialonska_cif.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; brucinium N-(4-nitrobenzoyl)-L-asparaginate methanol trisolvate ; _chemical_name_common ;brucinium N-(4-nitrobenzoyl)-L-asparaginate methanol trisolvate ; _chemical_melting_point ? _chemical_formula_moiety 'C23 H27 N2 O4, C11 H10 N3 O6, 3(C H4 O)' _chemical_formula_sum 'C37 H49 N5 O13' _chemical_formula_weight 771.81 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0000 '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 7.605(2) _cell_length_b 21.238(5) _cell_length_c 23.666(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3822.4(16) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 51278 _cell_measurement_theta_min 2.97 _cell_measurement_theta_max 35.25 _exptl_crystal_description needle _exptl_crystal_colour yellow _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 1.341 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1640 _exptl_absorpt_coefficient_mu 0.102 _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 48706 _diffrn_reflns_av_R_equivalents 0.0961 _diffrn_reflns_av_sigmaI/netI 0.0511 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 2.97 _diffrn_reflns_theta_max 27.50 _reflns_number_total 4917 _reflns_number_gt 4411 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.31.8 (release 12-01-2007 CrysAlis171 .NET) (compiled Jan 12 2007,17:49:11) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.8 (release 12-01-2007 CrysAlis171 .NET) (compiled Jan 12 2007,17:49:11) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.8 (release 12-01-2007 CrysAlis171 .NET) (compiled Jan 12 2007,17:49:11) ; _computing_structure_solution ; SHELXS-97 (Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.) ; _computing_structure_refinement ; SHELXL-97 (Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.) ; _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0769P)^2^+1.5601P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _chemical_absolute_configuration rm _refine_ls_abs_structure_details 'from known structure (Toda et al., 1985)' _refine_ls_number_reflns 4917 _refine_ls_number_parameters 558 _refine_ls_number_restraints 137 _refine_ls_R_factor_all 0.0845 _refine_ls_R_factor_gt 0.0711 _refine_ls_wR_factor_ref 0.1599 _refine_ls_wR_factor_gt 0.1540 _refine_ls_goodness_of_fit_ref 1.197 _refine_ls_restrained_S_all 1.204 _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 -0.0557(4) 0.72215(13) 1.02089(12) 0.0238(6) Uani 1 1 d . . . O2 O 0.2064(5) 0.57353(14) 0.68862(12) 0.0299(7) Uani 1 1 d . . . O3 O 0.3357(5) 0.47538(14) 0.73588(13) 0.0347(8) Uani 1 1 d . . . O4 O -0.0077(5) 0.74193(15) 0.82354(14) 0.0362(8) Uani 1 1 d . . . N1 N 0.1325(5) 0.66978(15) 0.87835(14) 0.0193(7) Uani 1 1 d . . . N2 N 0.2917(4) 0.52672(15) 1.01633(14) 0.0184(7) Uani 1 1 d . . . H24 H 0.3523 0.4892 1.0217 0.022 Uiso 1 1 calc R . . C1 C 0.1655(5) 0.62858(19) 0.77813(17) 0.0216(9) Uani 1 1 d . . . H1 H 0.1206 0.6654 0.7605 0.026 Uiso 1 1 calc R . . C2 C 0.2169(6) 0.5764(2) 0.74650(17) 0.0245(9) Uani 1 1 d . . . C3 C 0.2856(6) 0.52230(19) 0.77184(18) 0.0241(9) Uani 1 1 d . . . C4 C 0.3023(6) 0.52002(19) 0.83057(18) 0.0233(9) Uani 1 1 d . . . H4 H 0.3494 0.4837 0.8485 0.028 Uiso 1 1 calc R . . C5 C 0.2493(5) 0.57139(18) 0.86233(16) 0.0173(8) Uani 1 1 d . . . C6 C 0.1825(5) 0.62460(18) 0.83668(17) 0.0185(8) Uani 1 1 d . . . C7 C 0.2585(5) 0.58038(18) 0.92617(16) 0.0174(8) Uani 1 1 d . . . C8 C 0.1436(5) 0.64027(17) 0.93497(16) 0.0165(8) Uani 1 1 d . . . H8 H 0.2051 0.6696 0.9615 0.020 Uiso 1 1 calc R . . C9 C 0.0198(6) 0.71892(19) 0.87040(18) 0.0242(9) Uani 1 1 d . . . C10 C -0.0681(6) 0.74376(19) 0.92297(19) 0.0257(9) Uani 1 1 d . . . H10A H -0.1755 0.7666 0.9112 0.031 Uiso 1 1 calc R . . H10B H 0.0119 0.7750 0.9404 0.031 Uiso 1 1 calc R . . C11 C -0.1209(6) 0.69603(18) 0.96907(17) 0.0223(9) Uani 1 1 d . . . H11 H -0.2520 0.6934 0.9710 0.027 Uiso 1 1 calc R . . C12 C -0.1071(6) 0.6885(2) 1.07121(18) 0.0299(10) Uani 1 1 d . . . H12A H -0.2258 0.6704 1.0657 0.036 Uiso 1 1 calc R . . H12B H -0.1131 0.7183 1.1033 0.036 Uiso 1 1 calc R . . C13 C 0.0197(5) 0.6368(2) 1.08499(17) 0.0229(9) Uani 1 1 d . . . H13 H 0.0879 0.6401 1.1185 0.028 Uiso 1 1 calc R . . C14 C 0.0406(5) 0.58664(18) 1.05237(16) 0.0193(8) Uani 1 1 d . . . C15 C 0.1712(5) 0.53541(18) 1.06600(16) 0.0186(8) Uani 1 1 d . . . H15A H 0.2402 0.5472 1.0999 0.022 Uiso 1 1 calc R . . H15B H 0.1084 0.4956 1.0741 0.022 Uiso 1 1 calc R . . C16 C 0.4261(5) 0.57866(19) 1.01161(17) 0.0204(8) Uani 1 1 d . . . H16A H 0.5392 0.5655 1.0286 0.024 Uiso 1 1 calc R . . H16B H 0.3845 0.6171 1.0311 0.024 Uiso 1 1 calc R . . C17 C 0.4478(5) 0.5907(2) 0.94873(17) 0.0217(9) Uani 1 1 d . . . H17A H 0.5314 0.5606 0.9315 0.026 Uiso 1 1 calc R . . H17B H 0.4887 0.6342 0.9414 0.026 Uiso 1 1 calc R . . C18 C -0.0464(5) 0.63078(18) 0.95485(16) 0.0160(8) Uani 1 1 d . . . H18A H -0.1127 0.6164 0.9207 0.019 Uiso 1 1 calc R . . C19 C -0.0634(5) 0.57733(18) 0.99785(15) 0.0175(8) Uani 1 1 d . . . H19 H -0.1905 0.5722 1.0077 0.021 Uiso 1 1 calc R . . C20 C -0.0006(5) 0.51713(18) 0.96832(16) 0.0170(8) Uani 1 1 d . . . H20A H -0.0284 0.4799 0.9918 0.020 Uiso 1 1 calc R . . H20B H -0.0605 0.5124 0.9314 0.020 Uiso 1 1 calc R . . C21 C 0.1958(5) 0.52210(18) 0.95969(15) 0.0168(8) Uani 1 1 d . . . H21 H 0.2372 0.4834 0.9397 0.020 Uiso 1 1 calc R . . C22 C 0.1478(9) 0.6285(3) 0.6599(2) 0.0444(14) Uani 1 1 d . . . H22A H 0.1463 0.6206 0.6191 0.067 Uiso 1 1 calc R . . H22B H 0.2277 0.6635 0.6682 0.067 Uiso 1 1 calc R . . H22C H 0.0289 0.6393 0.6727 0.067 Uiso 1 1 calc R . . C23 C 0.3745(9) 0.4156(2) 0.7598(2) 0.0457(14) Uani 1 1 d . . . H23A H 0.4082 0.3863 0.7298 0.069 Uiso 1 1 calc R . . H23B H 0.2704 0.3995 0.7795 0.069 Uiso 1 1 calc R . . H23C H 0.4717 0.4199 0.7867 0.069 Uiso 1 1 calc R . . O5 O 0.4536(4) 0.41504(13) 1.01744(13) 0.0274(7) Uani 1 1 d . . . O6 O 0.5709(5) 0.44215(15) 0.93478(13) 0.0367(8) Uani 1 1 d . . . O7 O 0.9231(5) 0.25351(15) 0.93600(15) 0.0372(8) Uani 1 1 d . . . O8 O 0.8997(5) 0.41183(17) 1.06265(13) 0.0415(9) Uani 1 1 d . . . O9 O 0.8976(6) 0.23139(16) 1.31579(14) 0.0426(9) Uani 1 1 d . . . O10 O 0.8682(5) 0.32750(16) 1.34419(13) 0.0374(8) Uani 1 1 d . . . N3 N 0.7174(5) 0.33211(16) 1.04088(14) 0.0189(7) Uani 1 1 d . . . H3 H 0.639(6) 0.310(2) 1.0551(18) 0.016(11) Uiso 1 1 d . . . N4 N 0.7089(6) 0.19130(18) 0.96998(18) 0.0354(10) Uani 1 1 d . . . H47A H 0.7801 0.1589 0.9738 0.043 Uiso 1 1 calc R . . H47B H 0.5974 0.1878 0.9794 0.043 Uiso 1 1 calc R . . N5 N 0.8715(6) 0.28731(19) 1.30723(15) 0.0316(9) Uani 1 1 d . . . C24 C 0.5638(6) 0.40892(19) 0.97805(18) 0.0233(9) Uani 1 1 d . . . C25 C 0.6972(6) 0.35391(18) 0.98298(16) 0.0202(8) Uani 1 1 d . . . H25 H 0.8141 0.3690 0.9692 0.024 Uiso 1 1 calc R . . C26 C 0.6382(6) 0.29919(19) 0.94570(17) 0.0231(9) Uani 1 1 d . . . H26A H 0.5208 0.2844 0.9580 0.028 Uiso 1 1 calc R . . H26B H 0.6290 0.3134 0.9060 0.028 Uiso 1 1 calc R . . C27 C 0.7697(6) 0.2456(2) 0.94987(16) 0.0234(9) Uani 1 1 d . . . C28 C 0.8128(5) 0.36573(18) 1.07720(17) 0.0203(8) Uani 1 1 d . . . C29 C 0.8190(5) 0.34349(18) 1.13793(17) 0.0195(8) Uani 1 1 d . . . C30 C 0.8722(6) 0.3868(2) 1.17837(18) 0.0251(9) Uani 1 1 d . . . H30 H 0.9001 0.4287 1.1676 0.030 Uiso 1 1 calc R . . C31 C 0.8844(6) 0.3687(2) 1.23437(17) 0.0239(9) Uani 1 1 d . . . H31 H 0.9188 0.3980 1.2626 0.029 Uiso 1 1 calc R . . C32 C 0.8455(6) 0.3071(2) 1.24847(17) 0.0231(9) Uani 1 1 d . . . C33 C 0.7894(7) 0.2634(2) 1.20942(18) 0.0314(11) Uani 1 1 d . . . H33 H 0.7602 0.2217 1.2205 0.038 Uiso 1 1 calc R . . C34 C 0.7767(7) 0.2821(2) 1.15297(18) 0.0287(10) Uani 1 1 d . . . H34 H 0.7392 0.2530 1.1250 0.034 Uiso 1 1 calc R . . O35 O -0.1903(5) 0.44486(14) 0.84973(14) 0.0352(8) Uani 1 1 d . . . H35 H -0.2811 0.4431 0.8794 0.053 Uiso 1 1 d R . . C35 C -0.2094(7) 0.5026(2) 0.81983(19) 0.0336(11) Uani 1 1 d . . . H35A H -0.0930 0.5207 0.8126 0.050 Uiso 1 1 calc R . . H35B H -0.2792 0.5321 0.8425 0.050 Uiso 1 1 calc R . . H35C H -0.2690 0.4948 0.7838 0.050 Uiso 1 1 calc R . . O36 O 0.4723(15) 0.6216(4) 1.1446(3) 0.055(2) Uani 0.540(11) 1 d PDU A 1 H36 H 0.4926 0.6573 1.1586 0.083 Uiso 0.540(11) 1 calc PR A 1 C36 C 0.571(2) 0.5752(6) 1.1741(6) 0.064(3) Uani 0.540(11) 1 d PDU A 1 H36A H 0.6003 0.5406 1.1484 0.096 Uiso 0.540(11) 1 calc PR A 1 H36B H 0.5020 0.5590 1.2058 0.096 Uiso 0.540(11) 1 calc PR A 1 H36C H 0.6802 0.5941 1.1885 0.096 Uiso 0.540(11) 1 calc PR A 1 O361 O 0.5690(18) 0.5969(6) 1.1415(5) 0.066(3) Uani 0.460(11) 1 d PDU A 2 H361 H 0.5651 0.6179 1.1715 0.100 Uiso 0.460(11) 1 calc PR A 2 C361 C 0.650(2) 0.5377(7) 1.1523(7) 0.068(3) Uani 0.460(11) 1 d PDU A 2 H36D H 0.7667 0.5445 1.1689 0.102 Uiso 0.460(11) 1 calc PR A 2 H36E H 0.6625 0.5144 1.1167 0.102 Uiso 0.460(11) 1 calc PR A 2 H36F H 0.5774 0.5134 1.1786 0.102 Uiso 0.460(11) 1 calc PR A 2 O37 O -0.104(2) 0.3564(5) 0.7628(6) 0.078(3) Uani 0.427(11) 1 d PDU B 1 H37 H -0.0335 0.3447 0.7376 0.117 Uiso 0.427(11) 1 calc PR B 1 C37 C -0.214(3) 0.3072(8) 0.7768(9) 0.058(4) Uani 0.427(11) 1 d PDU B 1 H37A H -0.3209 0.3238 0.7945 0.087 Uiso 0.427(11) 1 calc PR B 1 H37B H -0.1536 0.2792 0.8034 0.087 Uiso 0.427(11) 1 calc PR B 1 H37C H -0.2450 0.2837 0.7426 0.087 Uiso 0.427(11) 1 calc PR B 1 O371 O -0.025(2) 0.3450(8) 0.7989(9) 0.073(3) Uani 0.315(11) 1 d PDU C 2 H371 H -0.0614 0.3801 0.8105 0.109 Uiso 0.315(11) 1 calc PR C 2 C371 C -0.167(3) 0.3057(13) 0.7902(14) 0.062(4) Uani 0.315(11) 1 d PDU C 2 H37D H -0.1640 0.2715 0.8180 0.093 Uiso 0.315(11) 1 calc PR C 2 H37E H -0.1606 0.2880 0.7520 0.093 Uiso 0.315(11) 1 calc PR C 2 H37F H -0.2762 0.3296 0.7945 0.093 Uiso 0.315(11) 1 calc PR C 2 O372 O 0.065(3) 0.3563(9) 0.8390(8) 0.079(4) Uani 0.258(8) 1 d PDU D 3 H37J H -0.0217 0.3795 0.8323 0.118 Uiso 0.258(8) 1 calc PR D 3 C372 C 0.132(3) 0.3706(9) 0.8915(8) 0.044(5) Uani 0.258(8) 1 d PDU D 3 H37G H 0.2603 0.3660 0.8909 0.066 Uiso 0.258(8) 1 calc PR D 3 H37H H 0.0820 0.3418 0.9196 0.066 Uiso 0.258(8) 1 calc PR D 3 H37I H 0.1015 0.4140 0.9013 0.066 Uiso 0.258(8) 1 calc PR D 3 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 0.0241(15) 0.0231(14) 0.0242(14) -0.0089(12) -0.0061(13) 0.0026(13) O2 0.0412(19) 0.0299(16) 0.0187(14) 0.0003(13) 0.0005(14) -0.0001(15) O3 0.053(2) 0.0263(16) 0.0248(16) -0.0038(14) 0.0108(15) 0.0049(16) O4 0.044(2) 0.0293(17) 0.0354(18) 0.0128(15) 0.0084(16) 0.0140(15) N1 0.0209(17) 0.0135(15) 0.0236(17) -0.0002(14) 0.0006(14) 0.0004(14) N2 0.0170(16) 0.0169(15) 0.0213(16) -0.0003(14) 0.0019(14) 0.0022(14) C1 0.019(2) 0.023(2) 0.022(2) 0.0065(17) 0.0060(16) -0.0029(17) C2 0.025(2) 0.028(2) 0.0205(19) -0.0016(17) 0.0019(17) -0.0044(19) C3 0.026(2) 0.0189(19) 0.028(2) -0.0042(17) 0.0084(18) -0.0025(18) C4 0.022(2) 0.0161(18) 0.032(2) 0.0004(18) 0.0032(18) 0.0007(17) C5 0.0159(19) 0.0181(18) 0.0178(18) 0.0018(16) 0.0039(15) -0.0016(15) C6 0.0158(19) 0.0178(18) 0.0217(19) -0.0022(16) 0.0036(15) -0.0061(16) C7 0.0180(19) 0.0163(18) 0.0178(18) -0.0038(16) 0.0046(15) 0.0014(15) C8 0.0196(19) 0.0114(16) 0.0185(19) -0.0013(15) -0.0003(16) -0.0044(15) C9 0.022(2) 0.0186(19) 0.032(2) 0.0019(19) 0.0030(18) -0.0024(17) C10 0.024(2) 0.0174(19) 0.035(2) -0.0041(18) -0.0006(19) 0.0047(18) C11 0.019(2) 0.0202(19) 0.028(2) -0.0086(17) -0.0031(17) 0.0010(17) C12 0.029(2) 0.039(2) 0.022(2) -0.0119(19) -0.0037(19) 0.013(2) C13 0.019(2) 0.032(2) 0.0178(19) -0.0069(18) -0.0022(16) 0.0003(18) C14 0.0175(19) 0.0206(19) 0.0198(19) -0.0015(17) 0.0031(15) -0.0040(16) C15 0.020(2) 0.0212(18) 0.0141(18) -0.0035(16) 0.0039(15) -0.0045(16) C16 0.0154(19) 0.0226(19) 0.023(2) -0.0026(17) -0.0002(16) -0.0013(16) C17 0.018(2) 0.0218(19) 0.025(2) -0.0002(17) 0.0031(17) 0.0000(17) C18 0.0139(18) 0.0176(18) 0.0164(18) -0.0048(15) -0.0010(15) -0.0010(15) C19 0.0117(18) 0.0230(19) 0.0177(18) -0.0041(16) 0.0029(15) -0.0029(16) C20 0.022(2) 0.0143(17) 0.0142(17) -0.0026(15) -0.0006(16) -0.0045(15) C21 0.022(2) 0.0143(17) 0.0137(17) -0.0013(15) 0.0045(16) 0.0008(16) C22 0.062(4) 0.050(3) 0.021(2) -0.001(2) -0.005(2) 0.019(3) C23 0.071(4) 0.026(2) 0.040(3) -0.008(2) 0.008(3) 0.010(3) O5 0.0363(18) 0.0196(14) 0.0263(15) 0.0060(13) 0.0101(14) 0.0098(14) O6 0.047(2) 0.0341(17) 0.0285(17) 0.0179(15) 0.0133(16) 0.0178(17) O7 0.0331(19) 0.0303(17) 0.048(2) 0.0109(16) 0.0145(16) 0.0123(15) O8 0.055(2) 0.0433(19) 0.0261(16) 0.0084(15) -0.0016(16) -0.0289(18) O9 0.063(3) 0.0364(19) 0.0281(17) 0.0088(15) -0.0104(17) 0.0079(18) O10 0.052(2) 0.0405(18) 0.0195(15) -0.0026(15) -0.0075(15) -0.0175(17) N3 0.0244(18) 0.0189(16) 0.0134(15) 0.0037(14) -0.0007(14) 0.0000(15) N4 0.035(2) 0.0244(18) 0.047(2) 0.0072(19) -0.015(2) 0.0018(18) N5 0.040(2) 0.036(2) 0.0192(18) 0.0007(17) -0.0090(17) -0.0035(19) C24 0.027(2) 0.0186(19) 0.024(2) 0.0011(18) 0.0019(18) 0.0019(18) C25 0.027(2) 0.0217(19) 0.0121(17) 0.0021(16) 0.0023(17) 0.0031(18) C26 0.027(2) 0.027(2) 0.0160(18) -0.0004(17) -0.0031(16) 0.0044(18) C27 0.035(3) 0.022(2) 0.0131(18) -0.0045(16) -0.0024(17) 0.0025(19) C28 0.022(2) 0.0198(19) 0.0192(19) -0.0018(17) 0.0042(17) 0.0006(17) C29 0.0142(19) 0.0216(19) 0.023(2) -0.0027(17) 0.0008(16) -0.0026(16) C30 0.032(2) 0.022(2) 0.021(2) 0.0036(17) -0.0017(19) -0.0107(18) C31 0.026(2) 0.026(2) 0.020(2) -0.0084(18) -0.0007(17) -0.0108(18) C32 0.026(2) 0.027(2) 0.0165(19) 0.0018(17) -0.0023(17) -0.0001(18) C33 0.053(3) 0.0160(19) 0.025(2) 0.0059(18) -0.009(2) -0.002(2) C34 0.046(3) 0.0194(19) 0.021(2) -0.0033(18) -0.007(2) 0.002(2) O35 0.043(2) 0.0290(16) 0.0331(17) -0.0012(14) 0.0099(16) 0.0018(16) C35 0.036(3) 0.045(3) 0.020(2) 0.006(2) 0.000(2) -0.005(2) O36 0.084(5) 0.037(4) 0.045(4) 0.001(3) -0.018(4) -0.006(4) C36 0.074(5) 0.059(5) 0.058(5) 0.017(4) -0.018(5) -0.006(5) O361 0.074(5) 0.072(5) 0.053(4) 0.012(4) -0.016(5) -0.005(4) C361 0.073(6) 0.072(6) 0.059(6) 0.019(5) -0.015(5) -0.004(5) O37 0.099(6) 0.057(4) 0.079(6) 0.002(4) 0.021(5) -0.002(5) C37 0.081(7) 0.032(5) 0.061(7) -0.005(5) 0.021(6) 0.010(5) O371 0.078(6) 0.057(5) 0.083(6) -0.007(5) 0.017(5) 0.012(5) C371 0.078(7) 0.041(5) 0.068(6) -0.002(5) 0.022(6) 0.008(5) O372 0.079(7) 0.064(6) 0.093(7) 0.003(6) 0.009(6) 0.009(6) C372 0.049(7) 0.025(7) 0.059(8) -0.008(6) -0.007(6) 0.003(6) _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 1.434(5) . ? O1 C12 1.442(6) . ? O2 C2 1.373(5) . ? O2 C22 1.422(6) . ? O3 C3 1.365(5) . ? O3 C23 1.421(6) . ? O4 C9 1.230(5) . ? N1 C9 1.363(5) . ? N1 C6 1.428(5) . ? N1 C8 1.482(5) . ? N2 C15 1.502(5) . ? N2 C16 1.508(5) . ? N2 C21 1.529(5) . ? N2 H24 0.9300 . ? C1 C2 1.393(6) . ? C1 C6 1.394(6) . ? C1 H1 0.9500 . ? C2 C3 1.397(6) . ? C3 C4 1.396(6) . ? C4 C5 1.385(6) . ? C4 H4 0.9500 . ? C5 C6 1.380(5) . ? C5 C7 1.524(5) . ? C7 C21 1.546(5) . ? C7 C17 1.551(6) . ? C7 C8 1.557(5) . ? C8 C18 1.533(5) . ? C8 H8 1.0000 . ? C9 C10 1.508(6) . ? C10 C11 1.542(6) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C18 1.534(5) . ? C11 H11 1.0000 . ? C12 C13 1.498(6) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.325(6) . ? C13 H13 0.9500 . ? C14 C15 1.508(6) . ? C14 C19 1.526(5) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 C17 1.519(6) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 C19 1.530(5) . ? C18 H18A 1.0000 . ? C19 C20 1.533(5) . ? C19 H19 1.0000 . ? C20 C21 1.511(6) . ? 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 1.261(5) . ? O6 C24 1.245(5) . ? O7 C27 1.223(6) . ? O8 C28 1.230(5) . ? O9 N5 1.221(5) . ? O10 N5 1.222(5) . ? N3 C28 1.332(5) . ? N3 C25 1.455(5) . ? N3 H3 0.83(5) . ? N4 C27 1.330(6) . ? N4 H47A 0.8800 . ? N4 H47B 0.8800 . ? N5 C32 1.466(5) . ? C24 C25 1.552(6) . ? C25 C26 1.526(6) . ? C25 H25 1.0000 . ? C26 C27 1.519(6) . ? C26 H26A 0.9900 . ? C26 H26B 0.9900 . ? C28 C29 1.514(6) . ? C29 C30 1.388(6) . ? C29 C34 1.389(6) . ? C30 C31 1.383(6) . ? C30 H30 0.9500 . ? C31 C32 1.383(6) . ? C31 H31 0.9500 . ? C32 C33 1.378(6) . ? C33 C34 1.397(6) . ? C33 H33 0.9500 . ? C34 H34 0.9500 . ? O35 C35 1.423(6) . ? O35 H35 0.9852 . ? C35 H35A 0.9800 . ? C35 H35B 0.9800 . ? C35 H35C 0.9800 . ? O36 C36 1.424(13) . ? O36 H36 0.8400 . ? C36 H36A 0.9800 . ? C36 H36B 0.9800 . ? C36 H36C 0.9800 . ? O361 C361 1.424(14) . ? O361 H361 0.8400 . ? C361 H36D 0.9800 . ? C361 H36E 0.9800 . ? C361 H36F 0.9800 . ? O37 C37 1.377(13) . ? O37 H37 0.8400 . ? C37 H37A 0.9800 . ? C37 H37B 0.9800 . ? C37 H37C 0.9800 . ? O371 C371 1.376(13) . ? O371 H371 0.8400 . ? C371 H37D 0.9800 . ? C371 H37E 0.9800 . ? C371 H37F 0.9800 . ? O372 C372 1.375(13) . ? O372 H37J 0.8400 . ? C372 H37G 0.9800 . ? C372 H37H 0.9800 . ? C372 H37I 0.9800 . ? 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(3) . . ? C2 O2 C22 117.3(3) . . ? C3 O3 C23 117.5(4) . . ? C9 N1 C6 125.9(4) . . ? C9 N1 C8 119.0(3) . . ? C6 N1 C8 109.0(3) . . ? C15 N2 C16 112.4(3) . . ? C15 N2 C21 113.8(3) . . ? C16 N2 C21 107.8(3) . . ? C15 N2 H24 107.5 . . ? C16 N2 H24 107.5 . . ? C21 N2 H24 107.5 . . ? C2 C1 C6 117.4(4) . . ? C2 C1 H1 121.3 . . ? C6 C1 H1 121.3 . . ? O2 C2 C1 123.7(4) . . ? O2 C2 C3 114.4(4) . . ? C1 C2 C3 121.9(4) . . ? O3 C3 C4 124.8(4) . . ? O3 C3 C2 115.9(4) . . ? C4 C3 C2 119.3(4) . . ? C5 C4 C3 119.1(4) . . ? C5 C4 H4 120.4 . . ? C3 C4 H4 120.4 . . ? C6 C5 C4 120.9(4) . . ? C6 C5 C7 110.5(3) . . ? C4 C5 C7 128.5(4) . . ? C5 C6 C1 121.4(4) . . ? C5 C6 N1 110.2(3) . . ? C1 C6 N1 128.4(4) . . ? C5 C7 C21 113.2(3) . . ? C5 C7 C17 113.7(3) . . ? C21 C7 C17 102.9(3) . . ? C5 C7 C8 102.1(3) . . ? C21 C7 C8 114.3(3) . . ? C17 C7 C8 111.0(3) . . ? N1 C8 C18 106.2(3) . . ? N1 C8 C7 104.9(3) . . ? C18 C8 C7 117.6(3) . . ? N1 C8 H8 109.3 . . ? C18 C8 H8 109.3 . . ? C7 C8 H8 109.3 . . ? O4 C9 N1 122.4(4) . . ? O4 C9 C10 122.0(4) . . ? N1 C9 C10 115.6(4) . . ? C9 C10 C11 118.0(3) . . ? C9 C10 H10A 107.8 . . ? C11 C10 H10A 107.8 . . ? C9 C10 H10B 107.8 . . ? C11 C10 H10B 107.8 . . ? H10A C10 H10B 107.1 . . ? O1 C11 C18 114.2(3) . . ? O1 C11 C10 105.1(3) . . ? C18 C11 C10 110.0(3) . . ? O1 C11 H11 109.1 . . ? C18 C11 H11 109.1 . . ? C10 C11 H11 109.1 . . ? O1 C12 C13 111.6(4) . . ? 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 122.7(4) . . ? C14 C13 H13 118.7 . . ? C12 C13 H13 118.7 . . ? C13 C14 C15 122.3(4) . . ? C13 C14 C19 122.3(4) . . ? C15 C14 C19 115.4(3) . . ? N2 C15 C14 108.8(3) . . ? 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 105.6(3) . . ? N2 C16 H16A 110.6 . . ? C17 C16 H16A 110.6 . . ? N2 C16 H16B 110.6 . . ? C17 C16 H16B 110.6 . . ? H16A C16 H16B 108.7 . . ? C16 C17 C7 102.3(3) . . ? 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 112.4(3) . . ? C19 C18 C11 119.5(3) . . ? C8 C18 C11 107.2(3) . . ? C19 C18 H18A 105.5 . . ? C8 C18 H18A 105.5 . . ? C11 C18 H18A 105.5 . . ? C14 C19 C18 115.0(3) . . ? C14 C19 C20 109.4(3) . . ? C18 C19 C20 106.8(3) . . ? C14 C19 H19 108.5 . . ? C18 C19 H19 108.5 . . ? C20 C19 H19 108.5 . . ? C21 C20 C19 108.2(3) . . ? C21 C20 H20A 110.1 . . ? C19 C20 H20A 110.1 . . ? C21 C20 H20B 110.1 . . ? C19 C20 H20B 110.1 . . ? H20A C20 H20B 108.4 . . ? C20 C21 N2 111.0(3) . . ? C20 C21 C7 115.5(3) . . ? N2 C21 C7 104.5(3) . . ? C20 C21 H21 108.5 . . ? N2 C21 H21 108.5 . . ? C7 C21 H21 108.5 . . ? 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 . . ? C28 N3 C25 119.7(4) . . ? C28 N3 H3 115(3) . . ? C25 N3 H3 119(3) . . ? C27 N4 H47A 120.0 . . ? C27 N4 H47B 120.0 . . ? H47A N4 H47B 120.0 . . ? O9 N5 O10 124.3(4) . . ? O9 N5 C32 117.3(4) . . ? O10 N5 C32 118.4(4) . . ? O6 C24 O5 125.4(4) . . ? O6 C24 C25 117.4(4) . . ? O5 C24 C25 117.2(3) . . ? N3 C25 C26 109.5(3) . . ? N3 C25 C24 112.3(3) . . ? C26 C25 C24 109.7(3) . . ? N3 C25 H25 108.4 . . ? C26 C25 H25 108.4 . . ? C24 C25 H25 108.4 . . ? C27 C26 C25 109.8(3) . . ? C27 C26 H26A 109.7 . . ? C25 C26 H26A 109.7 . . ? C27 C26 H26B 109.7 . . ? C25 C26 H26B 109.7 . . ? H26A C26 H26B 108.2 . . ? O7 C27 N4 123.1(4) . . ? O7 C27 C26 120.5(4) . . ? N4 C27 C26 116.3(4) . . ? O8 C28 N3 122.6(4) . . ? O8 C28 C29 119.8(4) . . ? N3 C28 C29 117.5(3) . . ? C30 C29 C34 120.9(4) . . ? C30 C29 C28 117.2(4) . . ? C34 C29 C28 121.9(4) . . ? C31 C30 C29 119.8(4) . . ? C31 C30 H30 120.1 . . ? C29 C30 H30 120.1 . . ? C32 C31 C30 118.7(4) . . ? C32 C31 H31 120.7 . . ? C30 C31 H31 120.7 . . ? C33 C32 C31 122.8(4) . . ? C33 C32 N5 119.0(4) . . ? C31 C32 N5 118.1(4) . . ? C32 C33 C34 118.1(4) . . ? C32 C33 H33 121.0 . . ? C34 C33 H33 121.0 . . ? C29 C34 C33 119.8(4) . . ? C29 C34 H34 120.1 . . ? C33 C34 H34 120.1 . . ? C35 O35 H35 108.4 . . ? O35 C35 H35A 109.5 . . ? O35 C35 H35B 109.5 . . ? H35A C35 H35B 109.5 . . ? O35 C35 H35C 109.5 . . ? H35A C35 H35C 109.5 . . ? H35B C35 H35C 109.5 . . ? C36 O36 H36 109.5 . . ? O36 C36 H36A 109.5 . . ? O36 C36 H36B 109.5 . . ? H36A C36 H36B 109.5 . . ? O36 C36 H36C 109.5 . . ? H36A C36 H36C 109.5 . . ? H36B C36 H36C 109.5 . . ? C361 O361 H361 109.5 . . ? O361 C361 H36D 109.5 . . ? O361 C361 H36E 109.5 . . ? H36D C361 H36E 109.5 . . ? O361 C361 H36F 109.5 . . ? H36D C361 H36F 109.5 . . ? H36E C361 H36F 109.5 . . ? C37 O37 H37 109.5 . . ? O37 C37 H37A 109.5 . . ? O37 C37 H37B 109.5 . . ? H37A C37 H37B 109.5 . . ? O37 C37 H37C 109.5 . . ? H37A C37 H37C 109.5 . . ? H37B C37 H37C 109.5 . . ? C371 O371 H371 109.5 . . ? O371 C371 H37D 109.5 . . ? O371 C371 H37E 109.5 . . ? H37D C371 H37E 109.5 . . ? O371 C371 H37F 109.5 . . ? H37D C371 H37F 109.5 . . ? H37E C371 H37F 109.5 . . ? C372 O372 H37J 109.5 . . ? O372 C372 H37G 109.5 . . ? O372 C372 H37H 109.5 . . ? H37G C372 H37H 109.5 . . ? O372 C372 H37I 109.5 . . ? H37G C372 H37I 109.5 . . ? H37H C372 H37I 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C22 O2 C2 C1 3.3(7) . . . . ? C22 O2 C2 C3 -176.2(4) . . . . ? C6 C1 C2 O2 179.5(4) . . . . ? C6 C1 C2 C3 -1.0(6) . . . . ? C23 O3 C3 C4 13.1(7) . . . . ? C23 O3 C3 C2 -168.4(5) . . . . ? O2 C2 C3 O3 1.4(6) . . . . ? C1 C2 C3 O3 -178.1(4) . . . . ? O2 C2 C3 C4 -180.0(4) . . . . ? C1 C2 C3 C4 0.5(7) . . . . ? O3 C3 C4 C5 178.8(4) . . . . ? C2 C3 C4 C5 0.4(6) . . . . ? C3 C4 C5 C6 -0.7(6) . . . . ? C3 C4 C5 C7 -178.4(4) . . . . ? C4 C5 C6 C1 0.2(6) . . . . ? C7 C5 C6 C1 178.3(4) . . . . ? C4 C5 C6 N1 178.1(4) . . . . ? C7 C5 C6 N1 -3.8(4) . . . . ? C2 C1 C6 C5 0.6(6) . . . . ? C2 C1 C6 N1 -176.9(4) . . . . ? C9 N1 C6 C5 -160.6(4) . . . . ? C8 N1 C6 C5 -8.7(4) . . . . ? C9 N1 C6 C1 17.2(7) . . . . ? C8 N1 C6 C1 169.1(4) . . . . ? C6 C5 C7 C21 137.0(4) . . . . ? C4 C5 C7 C21 -45.1(6) . . . . ? C6 C5 C7 C17 -106.0(4) . . . . ? C4 C5 C7 C17 71.9(5) . . . . ? C6 C5 C7 C8 13.7(4) . . . . ? C4 C5 C7 C8 -168.4(4) . . . . ? C9 N1 C8 C18 45.9(4) . . . . ? C6 N1 C8 C18 -108.2(3) . . . . ? C9 N1 C8 C7 171.0(3) . . . . ? C6 N1 C8 C7 16.9(4) . . . . ? C5 C7 C8 N1 -17.9(4) . . . . ? C21 C7 C8 N1 -140.5(3) . . . . ? C17 C7 C8 N1 103.6(3) . . . . ? C5 C7 C8 C18 99.8(4) . . . . ? C21 C7 C8 C18 -22.8(5) . . . . ? C17 C7 C8 C18 -138.7(3) . . . . ? C6 N1 C9 O4 -24.0(6) . . . . ? C8 N1 C9 O4 -173.4(4) . . . . ? C6 N1 C9 C10 156.5(4) . . . . ? C8 N1 C9 C10 7.1(5) . . . . ? O4 C9 C10 C11 144.0(4) . . . . ? N1 C9 C10 C11 -36.5(5) . . . . ? C12 O1 C11 C18 -65.9(4) . . . . ? C12 O1 C11 C10 173.4(3) . . . . ? C9 C10 C11 O1 131.5(4) . . . . ? C9 C10 C11 C18 8.2(5) . . . . ? C11 O1 C12 C13 88.0(4) . . . . ? O1 C12 C13 C14 -66.3(5) . . . . ? C12 C13 C14 C15 178.8(4) . . . . ? C12 C13 C14 C19 -0.1(6) . . . . ? C16 N2 C15 C14 75.4(4) . . . . ? C21 N2 C15 C14 -47.5(4) . . . . ? C13 C14 C15 N2 -124.7(4) . . . . ? C19 C14 C15 N2 54.2(4) . . . . ? C15 N2 C16 C17 -142.9(3) . . . . ? C21 N2 C16 C17 -16.7(4) . . . . ? N2 C16 C17 C7 35.7(4) . . . . ? C5 C7 C17 C16 -163.8(3) . . . . ? C21 C7 C17 C16 -41.0(4) . . . . ? C8 C7 C17 C16 81.8(4) . . . . ? N1 C8 C18 C19 154.9(3) . . . . ? C7 C8 C18 C19 38.0(4) . . . . ? N1 C8 C18 C11 -71.7(4) . . . . ? C7 C8 C18 C11 171.3(3) . . . . ? O1 C11 C18 C19 55.1(5) . . . . ? C10 C11 C18 C19 173.0(3) . . . . ? O1 C11 C18 C8 -74.3(4) . . . . ? C10 C11 C18 C8 43.6(4) . . . . ? C13 C14 C19 C18 56.4(5) . . . . ? C15 C14 C19 C18 -122.6(4) . . . . ? C13 C14 C19 C20 176.5(4) . . . . ? C15 C14 C19 C20 -2.5(4) . . . . ? C8 C18 C19 C14 60.9(4) . . . . ? C11 C18 C19 C14 -66.1(5) . . . . ? C8 C18 C19 C20 -60.6(4) . . . . ? C11 C18 C19 C20 172.4(3) . . . . ? C14 C19 C20 C21 -55.3(4) . . . . ? C18 C19 C20 C21 69.7(4) . . . . ? C19 C20 C21 N2 62.1(4) . . . . ? C19 C20 C21 C7 -56.7(4) . . . . ? C15 N2 C21 C20 -9.0(4) . . . . ? C16 N2 C21 C20 -134.4(3) . . . . ? C15 N2 C21 C7 116.2(3) . . . . ? C16 N2 C21 C7 -9.2(4) . . . . ? C5 C7 C21 C20 -83.8(4) . . . . ? C17 C7 C21 C20 153.1(3) . . . . ? C8 C7 C21 C20 32.6(5) . . . . ? C5 C7 C21 N2 154.0(3) . . . . ? C17 C7 C21 N2 30.9(4) . . . . ? C8 C7 C21 N2 -89.6(4) . . . . ? C28 N3 C25 C26 161.3(4) . . . . ? C28 N3 C25 C24 -76.5(5) . . . . ? O6 C24 C25 N3 160.9(4) . . . . ? O5 C24 C25 N3 -21.3(5) . . . . ? O6 C24 C25 C26 -77.1(5) . . . . ? O5 C24 C25 C26 100.8(4) . . . . ? N3 C25 C26 C27 -57.0(4) . . . . ? C24 C25 C26 C27 179.3(3) . . . . ? C25 C26 C27 O7 -60.3(5) . . . . ? C25 C26 C27 N4 118.7(4) . . . . ? C25 N3 C28 O8 -7.2(6) . . . . ? C25 N3 C28 C29 175.7(4) . . . . ? O8 C28 C29 C30 21.5(6) . . . . ? N3 C28 C29 C30 -161.4(4) . . . . ? O8 C28 C29 C34 -157.4(4) . . . . ? N3 C28 C29 C34 19.7(6) . . . . ? C34 C29 C30 C31 0.4(7) . . . . ? C28 C29 C30 C31 -178.5(4) . . . . ? C29 C30 C31 C32 1.0(7) . . . . ? C30 C31 C32 C33 -2.2(7) . . . . ? C30 C31 C32 N5 175.6(4) . . . . ? O9 N5 C32 C33 23.0(7) . . . . ? O10 N5 C32 C33 -158.1(5) . . . . ? O9 N5 C32 C31 -154.9(5) . . . . ? O10 N5 C32 C31 24.0(7) . . . . ? C31 C32 C33 C34 2.0(8) . . . . ? N5 C32 C33 C34 -175.8(4) . . . . ? C30 C29 C34 C33 -0.7(7) . . . . ? C28 C29 C34 C33 178.2(4) . . . . ? C32 C33 C34 C29 -0.5(7) . . . . ? 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 H24 O5 0.93 1.76 2.673(4) 168.2 . N3 H3 O7 0.83(5) 2.14(5) 2.935(5) 162(4) 4_457 N4 H47A O5 0.88 2.06 2.941(5) 178.2 4_557 O35 H35 O6 0.99 1.73 2.712(5) 175.8 1_455 O36 H36 O4 0.84 2.18 2.998(9) 163.7 4_567 O37 H37 O36 0.84 2.36 3.008(15) 134.2 2_564 O371 H371 O35 0.84 1.93 2.741(16) 162.9 . O372 H37J O35 0.84 1.93 2.72(2) 154.4 . _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.652 _refine_diff_density_min -0.303 _refine_diff_density_rms 0.056 #===== end of cif