# 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 'Agata Bialonska' _publ_contact_author_email AGATA.BIALONSKA@GMAIL.COM _publ_section_title ; Crucial factors influencing on racemic resolution of N-(4-nitrobenzoyl)-DL-serine by brucine ; loop_ _publ_author_name 'Agata Bialonska' 'Zbigniew Ciunik' # Attachment 'bialonska1.cif' data_1 _database_code_depnum_ccdc_archive 'CCDC 758142' #TrackingRef 'bialonska1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; brucinium N-(4-nitrobenzoyl)-(DL)-serinate trihydrate ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C23 H27 N2 O4, C10 H9 N2 O6, 3(H2 O)' _chemical_formula_sum 'C33 H42 N4 O13' _chemical_formula_weight 702.71 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+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 7.174(2) _cell_length_b 12.459(3) _cell_length_c 35.802(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3200.0(12) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 10366 _cell_measurement_theta_min 2.83 _cell_measurement_theta_max 36.82 _exptl_crystal_description plate _exptl_crystal_colour orange _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.459 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1488 _exptl_absorpt_coefficient_mu 0.113 _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 40247 _diffrn_reflns_av_R_equivalents 0.0808 _diffrn_reflns_av_sigmaI/netI 0.0378 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -48 _diffrn_reflns_limit_l_max 48 _diffrn_reflns_theta_min 3.06 _diffrn_reflns_theta_max 29.00 _reflns_number_total 4764 _reflns_number_gt 4345 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET) (compiled May 8 2007,13:10:02) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET) (compiled May 8 2007,13:10:02) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET) (compiled May 8 2007,13:10:02) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1159P)^2^+2.8021P] 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 4764 _refine_ls_number_parameters 642 _refine_ls_number_restraints 369 _refine_ls_R_factor_all 0.0864 _refine_ls_R_factor_gt 0.0800 _refine_ls_wR_factor_ref 0.2146 _refine_ls_wR_factor_gt 0.2101 _refine_ls_goodness_of_fit_ref 1.092 _refine_ls_restrained_S_all 1.070 _refine_ls_shift/su_max 0.003 _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 O8 O 0.4870(10) -0.0406(4) 0.17167(11) 0.113(2) Uani 1 1 d . . . O9 O 0.4490(7) -0.4419(3) 0.04081(10) 0.0768(12) Uani 1 1 d . . . O10 O 0.4283(6) -0.5629(3) 0.08419(12) 0.0708(11) Uani 1 1 d . . . N3 N 0.432(2) -0.1414(8) 0.2197(2) 0.077(4) Uani 0.50 1 d P A . H3 H 0.4173 -0.2045 0.2290 0.092 Uiso 0.50 1 d PR . . N3A N 0.528(2) -0.1734(11) 0.2169(3) 0.090(4) Uani 0.50 1 d P A . H3A H 0.5415 -0.2410 0.2208 0.108 Uiso 0.50 1 d PR . . N4 N 0.4460(6) -0.4690(3) 0.07362(13) 0.0587(10) Uani 1 1 d . . . C25 C 0.3982(11) -0.0481(6) 0.2449(2) 0.078(3) Uani 0.50 1 d PDU . . C251 C 0.5636(16) -0.0967(7) 0.2446(2) 0.095(4) Uani 0.50 1 d PDU A . C27 C 0.4790(10) -0.1320(5) 0.18309(14) 0.0744(17) Uani 1 1 d . . . C28 C 0.4762(6) -0.2254(4) 0.15551(12) 0.0461(10) Uani 1 1 d . . . C29 C 0.5282(6) -0.2037(4) 0.11870(11) 0.0458(9) Uani 1 1 d . . . H29 H 0.5685 -0.1354 0.1121 0.055 Uiso 1 1 calc R A . C30 C 0.5196(6) -0.2841(4) 0.09211(12) 0.0473(10) Uani 1 1 d . . . H30 H 0.5551 -0.2705 0.0676 0.057 Uiso 1 1 calc R . . C31 C 0.4576(6) -0.3847(3) 0.10243(12) 0.0460(9) Uani 1 1 d . . . C32 C 0.4077(6) -0.4087(4) 0.13866(13) 0.0532(11) Uani 1 1 d . . . H32 H 0.3684 -0.4773 0.1451 0.064 Uiso 1 1 calc R . . C33 C 0.4174(7) -0.3285(4) 0.16503(12) 0.0540(11) Uani 1 1 d . . . H33 H 0.3842 -0.3434 0.1896 0.065 Uiso 1 1 calc R A . O5 O 0.361(2) -0.071(2) 0.3102(4) 0.154(4) Uani 0.25 1 d PDU A 1 O6 O 0.6227(15) -0.130(2) 0.2847(6) 0.148(3) Uani 0.25 1 d PDU A 1 O5A O 0.462(5) -0.1945(9) 0.2898(9) 0.153(4) Uani 0.25 1 d PDU A 1 O6A O 0.3003(17) -0.073(2) 0.2773(8) 0.144(3) Uani 0.25 1 d PDU A 1 C24 C 0.4610(14) -0.0981(10) 0.2840(3) 0.146(3) Uani 0.50 1 d PDU A 1 O7 O 0.445(3) 0.1691(16) 0.2383(8) 0.127(4) Uani 0.25 1 d PDU A 1 C26 C 0.316(4) 0.0535(12) 0.2485(11) 0.131(4) Uani 0.25 1 d PDU A 1 O7A O 0.781(5) -0.052(2) 0.2920(5) 0.148(4) Uani 0.25 1 d PDU A 1 C26A C 0.758(2) -0.085(4) 0.2449(7) 0.141(4) Uani 0.25 1 d PDU A 1 O51 O 0.552(3) 0.1267(8) 0.2469(8) 0.123(3) Uani 0.25 1 d PDU A 2 O61 O 0.7246(15) -0.0141(18) 0.2409(8) 0.137(3) Uani 0.25 1 d PDU A 2 O5B O 0.465(3) 0.1043(14) 0.2491(8) 0.126(3) Uani 0.25 1 d PDU A 2 O6B O 0.7240(19) 0.070(2) 0.2525(7) 0.133(3) Uani 0.25 1 d PDU A 2 C241 C 0.5734(15) 0.0301(9) 0.2447(6) 0.128(3) Uani 0.50 1 d PDU A 2 O71 O 0.125(4) -0.1095(19) 0.2815(8) 0.139(5) Uani 0.25 1 d PDU A 2 C261 C 0.221(3) -0.009(2) 0.2537(10) 0.138(4) Uani 0.25 1 d PDU A 2 O7B O 0.787(5) -0.255(2) 0.2630(9) 0.143(9) Uani 0.25 1 d PDU . 2 C26B C 0.681(5) -0.132(3) 0.2735(7) 0.145(3) Uani 0.25 1 d PDU A 2 O2W O -0.032(3) 0.1575(17) 0.2417(5) 0.082(5) Uani 0.25 1 d PU B 1 O3W O 0.246(4) -0.1665(19) 0.2859(6) 0.097(6) Uani 0.25 1 d PU A 1 O21W O -0.121(3) 0.2153(16) 0.2392(5) 0.074(4) Uani 0.25 1 d PU C 2 O31W O 0.276(4) 0.158(2) 0.2460(7) 0.120(7) Uani 0.25 1 d PU . 2 O22W O -0.174(3) 0.1558(19) 0.2397(5) 0.084(5) Uani 0.25 1 d PU D 3 O32W O 0.085(5) -0.105(3) 0.2481(8) 0.145(9) Uani 0.25 1 d PU E 3 O23W O 0.111(5) 0.188(3) 0.2400(9) 0.130(8) Uani 0.25 1 d PU F 4 O33W O -0.011(7) -0.508(4) 0.2261(12) 0.199(11) Uani 0.25 1 d PU G 4 O1 O 0.0828(3) -1.01352(17) 0.04428(7) 0.0322(5) Uani 1 1 d . . . O2 O -0.0461(4) -0.31197(18) 0.05352(7) 0.0357(6) Uani 1 1 d . . . O3 O -0.0515(4) -0.32434(18) 0.12576(7) 0.0369(6) Uani 1 1 d . . . O4 O 0.0828(4) -0.66833(19) -0.01103(7) 0.0328(5) Uani 1 1 d . . . N1 N -0.0200(4) -0.7085(2) 0.04776(7) 0.0251(5) Uani 1 1 d . . . N2 N -0.0777(5) -0.8557(3) 0.16563(9) 0.0396(7) Uani 1 1 d . . . H2 H -0.1032 -0.8394 0.1899 0.048 Uiso 1 1 d R . . C1 C -0.0288(4) -0.5049(2) 0.04596(9) 0.0261(6) Uani 1 1 d . . . H1 H -0.0208 -0.5001 0.0201 0.031 Uiso 1 1 calc R . . C2 C -0.0410(5) -0.4133(2) 0.06811(10) 0.0289(6) Uani 1 1 d . . . C3 C -0.0491(5) -0.4206(2) 0.10717(9) 0.0302(7) Uani 1 1 d . . . C4 C -0.0531(5) -0.5201(3) 0.12421(9) 0.0292(6) Uani 1 1 d . . . H4 H -0.0613 -0.5252 0.1501 0.035 Uiso 1 1 calc R . . C5 C -0.0449(4) -0.6127(2) 0.10252(9) 0.0274(6) Uani 1 1 d . . . C6 C -0.0289(4) -0.6048(2) 0.06404(9) 0.0246(6) Uani 1 1 d . . . C7 C -0.0692(5) -0.7282(2) 0.11381(9) 0.0260(6) Uani 1 1 d . . . C8 C -0.0171(4) -0.7906(2) 0.07795(9) 0.0248(6) Uani 1 1 d . . . H8 H -0.1123 -0.8451 0.0729 0.030 Uiso 1 1 calc R . . C9 C 0.0520(4) -0.7343(2) 0.01376(9) 0.0260(6) Uani 1 1 d . . . C10 C 0.0850(5) -0.8535(2) 0.00801(9) 0.0274(6) Uani 1 1 d . . . H10A H 0.1611 -0.8627 -0.0141 0.033 Uiso 1 1 calc R . . H10B H -0.0342 -0.8876 0.0032 0.033 Uiso 1 1 calc R . . C11 C 0.1810(4) -0.9131(2) 0.04105(9) 0.0262(6) Uani 1 1 d . . . H11 H 0.3110 -0.9276 0.0344 0.031 Uiso 1 1 calc R . . C12 C 0.1674(5) -1.0858(3) 0.07058(11) 0.0356(8) Uani 1 1 d . . . H12A H 0.3004 -1.0723 0.0718 0.043 Uiso 1 1 calc R . . H12B H 0.1489 -1.1593 0.0624 0.043 Uiso 1 1 calc R . . C13 C 0.0832(6) -1.0709(3) 0.10852(11) 0.0383(8) Uani 1 1 d . . . H13 H 0.0101 -1.1252 0.1187 0.046 Uiso 1 1 calc R . . C14 C 0.1110(5) -0.9818(3) 0.12786(11) 0.0363(8) Uani 1 1 d . . . C15 C 0.0236(7) -0.9628(3) 0.16498(11) 0.0441(9) Uani 1 1 d . . . H15A H 0.1191 -0.9634 0.1842 0.053 Uiso 1 1 calc R . . H15B H -0.0638 -1.0201 0.1704 0.053 Uiso 1 1 calc R . . C16 C -0.2608(6) -0.8597(3) 0.14473(12) 0.0424(9) Uani 1 1 d . . . H16A H -0.3642 -0.8699 0.1618 0.051 Uiso 1 1 calc R . . H16B H -0.2609 -0.9176 0.1266 0.051 Uiso 1 1 calc R . . C17 C -0.2735(5) -0.7511(3) 0.12541(11) 0.0358(8) Uani 1 1 d . . . H17A H -0.3195 -0.6964 0.1424 0.043 Uiso 1 1 calc R . . H17B H -0.3545 -0.7544 0.1037 0.043 Uiso 1 1 calc R . . C18 C 0.1768(5) -0.8422(2) 0.07597(9) 0.0258(6) Uani 1 1 d . . . H18 H 0.2642 -0.7834 0.0711 0.031 Uiso 1 1 calc R . . C19 C 0.2370(5) -0.8916(3) 0.11353(9) 0.0299(7) Uani 1 1 d . . . H19 H 0.3640 -0.9195 0.1109 0.036 Uiso 1 1 calc R . . C20 C 0.2389(5) -0.7988(3) 0.14208(10) 0.0329(7) Uani 1 1 d . . . H20A H 0.2959 -0.8226 0.1652 0.040 Uiso 1 1 calc R . . H20B H 0.3113 -0.7392 0.1324 0.040 Uiso 1 1 calc R . . C21 C 0.0412(5) -0.7633(3) 0.14925(9) 0.0333(7) Uani 1 1 d . . . H21 H 0.0427 -0.7037 0.1671 0.040 Uiso 1 1 calc R . . C22 C -0.0679(6) -0.3032(3) 0.01374(10) 0.0392(8) Uani 1 1 d . . . H22A H -0.0801 -0.2289 0.0070 0.059 Uiso 1 1 calc R . . H22B H -0.1776 -0.3415 0.0061 0.059 Uiso 1 1 calc R . . H22C H 0.0393 -0.3332 0.0016 0.059 Uiso 1 1 calc R . . C23 C -0.0685(6) -0.3294(3) 0.16537(11) 0.0414(9) Uani 1 1 d . . . H23A H -0.0668 -0.2580 0.1755 0.062 Uiso 1 1 calc R . . H23B H 0.0336 -0.3698 0.1755 0.062 Uiso 1 1 calc R . . H23C H -0.1839 -0.3637 0.1718 0.062 Uiso 1 1 calc R . . O1W O 0.6730(4) -0.0173(2) 0.05404(8) 0.0391(6) Uani 1 1 d . . . H11W H 0.7839 -0.0328 0.0467 0.059 Uiso 1 1 d R . . H12W H 0.6682 0.0381 0.0397 0.059 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 O8 0.188(5) 0.091(3) 0.061(2) 0.006(2) -0.012(3) -0.079(4) O9 0.113(3) 0.0507(18) 0.067(2) 0.0037(17) 0.036(2) 0.018(2) O10 0.069(2) 0.0394(15) 0.104(3) 0.0159(17) 0.017(2) 0.0151(17) N3 0.147(12) 0.046(5) 0.036(4) 0.004(3) 0.005(6) 0.000(7) N3A 0.131(12) 0.080(8) 0.058(6) 0.001(6) -0.002(7) 0.018(8) N4 0.054(2) 0.0436(18) 0.078(3) 0.0101(19) 0.022(2) 0.0183(18) C25 0.109(7) 0.089(6) 0.036(4) -0.004(4) 0.007(5) -0.008(6) C251 0.110(8) 0.116(8) 0.060(5) 0.004(6) -0.020(6) -0.002(7) C27 0.089(4) 0.086(4) 0.048(2) 0.015(3) -0.014(3) -0.038(3) C28 0.0394(19) 0.054(2) 0.0448(19) 0.0187(18) -0.0077(16) -0.0060(19) C29 0.0377(18) 0.054(2) 0.0455(19) 0.0207(18) -0.0050(16) -0.0041(18) C30 0.0374(18) 0.052(2) 0.052(2) 0.0244(19) 0.0127(16) 0.0119(18) C31 0.0348(18) 0.046(2) 0.058(2) 0.0173(18) 0.0058(18) 0.0132(17) C32 0.0406(19) 0.056(2) 0.063(2) 0.031(2) -0.0026(19) -0.003(2) C33 0.049(2) 0.072(3) 0.0405(19) 0.025(2) -0.0001(18) -0.015(2) O5 0.158(6) 0.151(6) 0.152(6) 0.001(5) 0.003(5) -0.003(5) O6 0.153(5) 0.150(5) 0.141(5) 0.003(4) -0.004(4) -0.002(4) O5A 0.157(6) 0.156(6) 0.145(6) -0.001(5) 0.001(5) -0.003(6) O6A 0.148(5) 0.144(5) 0.139(5) -0.002(4) 0.006(4) -0.004(4) C24 0.153(4) 0.148(4) 0.138(4) 0.001(4) 0.001(4) -0.002(4) O7 0.137(6) 0.129(6) 0.114(6) -0.015(5) -0.003(5) 0.001(5) C26 0.136(6) 0.136(6) 0.122(6) 0.001(6) -0.006(6) -0.003(6) O7A 0.151(6) 0.149(6) 0.144(6) 0.002(5) -0.009(5) -0.002(6) C26A 0.146(6) 0.141(6) 0.135(6) 0.000(6) 0.000(6) -0.004(6) O51 0.133(5) 0.129(5) 0.107(5) -0.014(4) -0.003(4) 0.001(4) O61 0.142(5) 0.142(5) 0.128(5) -0.007(5) -0.002(5) 0.003(5) O5B 0.136(5) 0.132(5) 0.109(5) -0.007(4) -0.003(4) 0.001(5) O6B 0.142(5) 0.135(5) 0.122(5) -0.007(5) -0.002(5) 0.002(5) C241 0.139(5) 0.134(5) 0.112(4) -0.008(4) -0.001(4) 0.003(4) O71 0.143(7) 0.142(7) 0.133(7) -0.002(6) 0.010(6) -0.002(7) C261 0.142(6) 0.142(6) 0.130(6) 0.000(6) -0.003(6) -0.004(6) O7B 0.146(12) 0.142(11) 0.141(11) 0.006(8) -0.016(8) 0.006(9) C26B 0.150(5) 0.147(5) 0.139(5) 0.001(5) -0.003(5) -0.001(5) O2W 0.098(9) 0.091(8) 0.057(7) -0.026(6) 0.005(7) -0.006(7) O3W 0.106(9) 0.106(9) 0.080(8) 0.013(7) 0.002(7) -0.010(8) O21W 0.080(8) 0.081(8) 0.062(7) -0.001(7) 0.007(6) -0.015(7) O31W 0.120(10) 0.127(11) 0.114(10) -0.018(8) -0.010(8) -0.005(8) O22W 0.097(9) 0.091(8) 0.063(7) -0.025(7) 0.010(7) -0.012(8) O32W 0.144(12) 0.147(11) 0.143(11) 0.015(8) 0.004(8) 0.017(9) O23W 0.128(11) 0.137(11) 0.126(11) 0.002(8) -0.005(8) 0.009(9) O33W 0.205(13) 0.201(14) 0.191(14) 0.011(9) -0.005(9) -0.002(9) O1 0.0331(11) 0.0191(9) 0.0444(12) 0.0038(9) -0.0067(10) -0.0035(9) O2 0.0449(14) 0.0192(9) 0.0430(12) 0.0003(9) -0.0071(12) -0.0001(10) O3 0.0452(14) 0.0220(10) 0.0434(13) -0.0087(10) -0.0068(12) -0.0003(11) O4 0.0325(12) 0.0262(10) 0.0396(12) 0.0037(10) 0.0013(10) 0.0020(10) N1 0.0247(12) 0.0181(10) 0.0324(12) 0.0015(10) -0.0013(10) -0.0005(10) N2 0.0450(17) 0.0362(15) 0.0377(14) 0.0099(13) 0.0074(14) 0.0020(15) C1 0.0260(13) 0.0195(12) 0.0329(14) 0.0028(11) -0.0024(12) 0.0010(11) C2 0.0250(13) 0.0216(13) 0.0400(15) 0.0002(12) -0.0091(13) -0.0023(12) C3 0.0276(14) 0.0229(13) 0.0401(16) -0.0077(13) -0.0060(14) 0.0001(12) C4 0.0312(15) 0.0260(13) 0.0304(14) -0.0028(12) -0.0012(13) 0.0006(13) C5 0.0241(13) 0.0223(12) 0.0357(15) 0.0012(12) 0.0010(12) 0.0001(12) C6 0.0199(12) 0.0196(12) 0.0341(14) -0.0033(11) -0.0012(11) -0.0032(11) C7 0.0274(14) 0.0212(12) 0.0293(13) 0.0013(11) 0.0038(12) -0.0005(12) C8 0.0240(13) 0.0200(12) 0.0304(14) 0.0025(11) -0.0015(11) -0.0028(11) C9 0.0222(13) 0.0231(12) 0.0326(14) 0.0015(11) 0.0002(12) -0.0027(11) C10 0.0280(14) 0.0218(12) 0.0323(14) -0.0007(12) 0.0021(13) 0.0027(12) C11 0.0215(12) 0.0169(12) 0.0402(16) 0.0005(12) -0.0014(12) -0.0016(11) C12 0.0383(17) 0.0201(13) 0.0485(18) 0.0026(14) -0.0108(16) -0.0020(14) C13 0.0395(18) 0.0275(15) 0.0480(19) 0.0123(14) -0.0040(16) -0.0046(15) C14 0.0371(17) 0.0278(14) 0.0440(18) 0.0090(15) -0.0022(15) -0.0029(14) C15 0.050(2) 0.0345(17) 0.0473(19) 0.0152(16) 0.0015(18) 0.0015(17) C16 0.0355(17) 0.0388(18) 0.053(2) 0.0118(17) 0.0106(17) -0.0052(16) C17 0.0324(16) 0.0309(16) 0.0440(18) 0.0038(15) 0.0119(15) 0.0015(13) C18 0.0238(13) 0.0187(12) 0.0348(15) 0.0018(12) -0.0011(12) -0.0018(12) C19 0.0314(15) 0.0224(13) 0.0360(15) 0.0004(13) -0.0045(13) 0.0004(13) C20 0.0394(17) 0.0266(14) 0.0328(15) 0.0026(13) -0.0070(14) -0.0009(14) C21 0.0426(18) 0.0288(14) 0.0284(14) 0.0025(13) -0.0008(14) -0.0045(15) C22 0.052(2) 0.0228(13) 0.0425(18) 0.0061(13) -0.0089(17) -0.0010(15) C23 0.045(2) 0.0327(16) 0.0463(19) -0.0090(16) -0.0038(17) 0.0036(17) O1W 0.0300(11) 0.0371(13) 0.0504(14) 0.0158(12) -0.0020(11) -0.0057(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O8 C27 1.211(7) . ? O9 N4 1.223(5) . ? O10 N4 1.236(5) . ? N3 N3A 0.800(18) . ? N3 C27 1.360(11) . ? N3 C251 1.413(16) . ? N3 C25 1.491(12) . ? N3 H3 0.8599 . ? N3 H3A 1.4687 . ? N3A C27 1.362(13) . ? N3A C251 1.401(16) . ? N3A H3 0.9840 . ? N3A H3A 0.8600 . ? N4 C31 1.475(6) . ? C25 C251 1.332(15) . ? C25 O6A 1.39(3) . ? C25 C261 1.402(16) . ? C25 C26 1.402(15) . ? C25 C241 1.590(12) . ? C25 C24 1.597(12) . ? C251 C26A 1.404(15) . ? C251 C26B 1.406(16) . ? C251 O61 1.55(2) . ? C251 O6 1.55(2) . ? C251 C241 1.581(12) . ? C251 C24 1.591(12) . ? C27 C28 1.526(8) . ? C28 C33 1.394(6) . ? C28 C29 1.396(6) . ? C29 C30 1.383(7) . ? C29 H29 0.9300 . ? C30 C31 1.380(6) . ? C30 H30 0.9300 . ? C31 C32 1.378(6) . ? C32 C33 1.376(7) . ? C32 H32 0.9300 . ? C33 H33 0.9300 . ? O5 C24 1.226(9) . ? O5 O6A 1.25(3) . ? O5 O3W 1.69(3) . ? O6 C24 1.228(8) . ? O6 O5A 1.42(4) . ? O6 O7A 1.52(4) . ? O6 C26A 1.81(3) . ? O5A C24 1.218(9) . ? O5A O3W 1.60(4) . ? O6A C24 1.220(9) . ? O6A O3W 1.27(3) . ? O6A C26 1.88(4) . ? C24 O3W 1.77(3) . ? O7 C26 1.75(2) . ? O7A C26A 1.74(2) . ? O51 O5B 0.69(3) . ? O51 C241 1.215(9) . ? O51 O6B 1.44(3) . ? O61 O6B 1.12(3) . ? O61 C241 1.224(9) . ? O61 C26B 1.91(4) . ? O5B C241 1.216(9) . ? O5B O31W 1.51(3) . ? O6B C241 1.219(10) . ? O71 C261 1.75(2) . ? O7B O31W 1.22(4) 4_645 ? O7B C26B 1.75(2) . ? O31W O7B 1.22(4) 4_655 ? O1 C12 1.438(4) . ? O1 C11 1.441(4) . ? O2 C2 1.367(4) . ? O2 C22 1.437(4) . ? O3 C3 1.372(4) . ? O3 C23 1.425(5) . ? O4 C9 1.230(4) . ? N1 C9 1.361(4) . ? N1 C6 1.419(4) . ? N1 C8 1.488(4) . ? N2 C16 1.512(5) . ? N2 C15 1.520(5) . ? N2 C21 1.548(5) . ? N2 H2 0.9102 . ? C1 C2 1.392(4) . ? C1 C6 1.402(4) . ? C1 H1 0.9300 . ? C2 C3 1.403(5) . ? C3 C4 1.382(4) . ? C4 C5 1.392(4) . ? C4 H4 0.9300 . ? C5 C6 1.386(4) . ? C5 C7 1.505(4) . ? C7 C8 1.547(4) . ? C7 C17 1.549(5) . ? C7 C21 1.559(5) . ? C8 C18 1.534(4) . ? C8 H8 0.9800 . ? C9 C10 1.517(4) . ? C10 C11 1.557(4) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C18 1.530(4) . ? C11 H11 0.9800 . ? C12 C13 1.498(6) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C14 1.323(5) . ? C13 H13 0.9300 . ? C14 C15 1.489(6) . ? C14 C19 1.531(5) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 C17 1.523(5) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 C19 1.540(4) . ? C18 H18 0.9800 . ? C19 C20 1.543(5) . ? C19 H19 0.9800 . ? C20 C21 1.507(5) . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C21 H21 0.9800 . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? O1W H11W 0.8600 . ? O1W H12W 0.8601 . ? 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 N3A N3 C27 73.0(13) . . ? N3A N3 C251 72.7(16) . . ? C27 N3 C251 114.2(11) . . ? N3A N3 C25 127.2(18) . . ? C27 N3 C25 123.8(8) . . ? C251 N3 C25 54.5(7) . . ? N3A N3 H3 72.6 . . ? C27 N3 H3 118.9 . . ? C251 N3 H3 101.5 . . ? C25 N3 H3 117.3 . . ? N3A N3 H3A 28.9 . . ? C27 N3 H3A 88.1 . . ? C251 N3 H3A 87.7 . . ? C25 N3 H3A 136.8 . . ? H3 N3 H3A 44.3 . . ? N3 N3A C27 72.8(13) . . ? N3 N3A C251 74.2(14) . . ? C27 N3A C251 114.8(10) . . ? N3 N3A H3 56.5 . . ? C27 N3A H3 109.5 . . ? C251 N3A H3 95.9 . . ? N3 N3A H3A 124.4 . . ? C27 N3A H3A 123.1 . . ? C251 N3A H3A 122.1 . . ? H3 N3A H3A 68.5 . . ? O9 N4 O10 123.9(5) . . ? O9 N4 C31 118.3(4) . . ? O10 N4 C31 117.8(4) . . ? C251 C25 O6A 110.9(8) . . ? C251 C25 C261 166.3(15) . . ? O6A C25 C261 55.3(15) . . ? C251 C25 C26 141.7(13) . . ? O6A C25 C26 84.8(18) . . ? C261 C25 C26 44.0(17) . . ? C251 C25 N3 59.7(8) . . ? O6A C25 N3 114.6(14) . . ? C261 C25 N3 123.9(17) . . ? C26 C25 N3 145.9(18) . . ? C251 C25 C241 64.8(4) . . ? O6A C25 C241 122.5(14) . . ? C261 C25 C241 120.2(14) . . ? C26 C25 C241 77.2(12) . . ? N3 C25 C241 110.3(9) . . ? C251 C25 C24 65.1(4) . . ? O6A C25 C24 47.6(6) . . ? C261 C25 C24 101.4(15) . . ? C26 C25 C24 113.0(18) . . ? N3 C25 C24 100.4(7) . . ? C241 C25 C24 91.1(9) . . ? C25 C251 N3A 98.7(10) . . ? C25 C251 C26A 147(2) . . ? N3A C251 C26A 104.8(17) . . ? C25 C251 C26B 132.1(15) . . ? N3A C251 C26B 114.5(17) . . ? C26A C251 C26B 55(2) . . ? C25 C251 N3 65.7(8) . . ? N3A C251 N3 33.0(7) . . ? C26A C251 N3 135.1(14) . . ? C26B C251 N3 137.6(18) . . ? C25 C251 O61 111.2(8) . . ? N3A C251 O61 121.9(13) . . ? C26A C251 O61 36(2) . . ? C26B C251 O61 80(2) . . ? N3 C251 O61 134.8(12) . . ? C25 C251 O6 111.0(7) . . ? N3A C251 O6 121.4(13) . . ? C26A C251 O6 75.5(14) . . ? C26B C251 O6 21.8(16) . . ? N3 C251 O6 131.2(12) . . ? O61 C251 O6 93.1(14) . . ? C25 C251 C241 65.5(5) . . ? N3A C251 C241 133.7(11) . . ? C26A C251 C241 82(2) . . ? C26B C251 C241 106.8(18) . . ? N3 C251 C241 115.2(10) . . ? O61 C251 C241 46.0(6) . . ? O6 C251 C241 104.8(14) . . ? C25 C251 C24 65.5(5) . . ? N3A C251 C24 122.4(10) . . ? C26A C251 C24 117.1(12) . . ? C26B C251 C24 67.7(15) . . ? N3 C251 C24 104.2(9) . . ? O61 C251 C24 115.3(12) . . ? O6 C251 C24 45.9(5) . . ? C241 C251 C24 91.7(9) . . ? O8 C27 N3 114.8(7) . . ? O8 C27 N3A 130.1(8) . . ? N3 C27 N3A 34.2(7) . . ? O8 C27 C28 119.9(5) . . ? N3 C27 C28 123.7(6) . . ? N3A C27 C28 106.8(7) . . ? C33 C28 C29 119.3(4) . . ? C33 C28 C27 123.3(4) . . ? C29 C28 C27 117.4(4) . . ? C30 C29 C28 119.8(4) . . ? C30 C29 H29 120.1 . . ? C28 C29 H29 120.1 . . ? C31 C30 C29 119.2(4) . . ? C31 C30 H30 120.4 . . ? C29 C30 H30 120.4 . . ? C32 C31 C30 122.1(4) . . ? C32 C31 N4 119.3(4) . . ? C30 C31 N4 118.6(4) . . ? C33 C32 C31 118.4(4) . . ? C33 C32 H32 120.8 . . ? C31 C32 H32 120.8 . . ? C32 C33 C28 121.1(4) . . ? C32 C33 H33 119.5 . . ? C28 C33 H33 119.5 . . ? C24 O5 O6A 58.9(9) . . ? C24 O5 O3W 72.5(14) . . ? O6A O5 O3W 48.4(16) . . ? C24 O6 O5A 54.3(11) . . ? C24 O6 O7A 120(2) . . ? O5A O6 O7A 162(2) . . ? C24 O6 C251 68.7(10) . . ? O5A O6 C251 92.8(17) . . ? O7A O6 C251 100.9(16) . . ? C24 O6 C26A 113.1(17) . . ? O5A O6 C26A 135(2) . . ? O7A O6 C26A 62.4(12) . . ? C251 O6 C26A 48.6(9) . . ? C24 O5A O6 54.9(11) . . ? C24 O5A O3W 76.4(19) . . ? O6 O5A O3W 131.1(15) . . ? C24 O6A O5 59.4(9) . . ? C24 O6A O3W 90(2) . . ? O5 O6A O3W 84(2) . . ? C24 O6A C25 75.1(12) . . ? O5 O6A C25 127.0(15) . . ? O3W O6A C25 124(3) . . ? C24 O6A C26 105.5(18) . . ? O5 O6A C26 119(3) . . ? O3W O6A C26 157(2) . . ? C25 O6A C26 47.9(12) . . ? O5A C24 O6A 107(3) . . ? O5A C24 O5 98(2) . . ? O6A C24 O5 61.7(16) . . ? O5A C24 O6 71(2) . . ? O6A C24 O6 169(2) . . ? O5 C24 O6 128.9(15) . . ? O5A C24 C251 99.1(19) . . ? O6A C24 C251 105.1(16) . . ? O5 C24 C251 160.7(14) . . ? O6 C24 C251 65.4(11) . . ? O5A C24 C25 122(2) . . ? O6A C24 C25 57.3(14) . . ? O5 C24 C25 113.3(11) . . ? O6 C24 C25 114.2(12) . . ? C251 C24 C25 49.4(6) . . ? O5A C24 O3W 61(2) . . ? O6A C24 O3W 46.0(16) . . ? O5 C24 O3W 66.0(14) . . ? O6 C24 O3W 132.0(17) . . ? C251 C24 O3W 116.3(11) . . ? C25 C24 O3W 88.5(9) . . ? C25 C26 O7 120.3(18) . . ? C25 C26 O6A 47.3(11) . . ? O7 C26 O6A 146(2) . . ? O6 O7A C26A 67.1(15) . . ? C251 C26A O7A 97.0(17) . . ? C251 C26A O6 56.0(10) . . ? O7A C26A O6 50.5(14) . . ? O5B O51 C241 73.7(10) . . ? O5B O51 O6B 124(2) . . ? C241 O51 O6B 54.0(10) . . ? O6B O61 C241 62.5(9) . . ? O6B O61 C251 125.6(15) . . ? C241 O61 C251 68.3(9) . . ? O6B O61 C26B 120(3) . . ? C241 O61 C26B 97.7(17) . . ? C251 O61 C26B 46.6(11) . . ? O51 O5B C241 73.5(11) . . ? O51 O5B O31W 129(3) . . ? C241 O5B O31W 153(2) . . ? O61 O6B C241 62.9(9) . . ? O61 O6B O51 114.4(14) . . ? C241 O6B O51 53.7(9) . . ? O51 C241 O5B 32.9(15) . . ? O51 C241 O6B 72.3(17) . . ? O5B C241 O6B 103.2(17) . . ? O51 C241 O61 124.2(19) . . ? O5B C241 O61 157.0(18) . . ? O6B C241 O61 54.6(16) . . ? O51 C241 C251 169.7(16) . . ? O5B C241 C251 137.0(15) . . ? O6B C241 C251 116.3(15) . . ? O61 C241 C251 65.8(11) . . ? O51 C241 C25 120.6(13) . . ? O5B C241 C25 87.9(13) . . ? O6B C241 C25 161(2) . . ? O61 C241 C25 115.1(11) . . ? C251 C241 C25 49.7(6) . . ? C25 C261 O71 103.4(18) . . ? O31W O7B C26B 132(3) 4_645 . ? C251 C26B O7B 112(2) . . ? C251 C26B O61 53.3(12) . . ? O7B C26B O61 118(2) . . ? O6A O3W O5A 85.5(16) . . ? O6A O3W O5 47.5(16) . . ? O5A O3W O5 68.4(13) . . ? O6A O3W C24 43.7(9) . . ? O5A O3W C24 42.1(7) . . ? O5 O3W C24 41.5(7) . . ? O7B O31W O5B 138(3) 4_655 . ? C12 O1 C11 113.0(2) . . ? C2 O2 C22 116.9(3) . . ? C3 O3 C23 116.5(3) . . ? C9 N1 C6 126.8(3) . . ? C9 N1 C8 118.8(2) . . ? C6 N1 C8 109.2(2) . . ? C16 N2 C15 112.3(3) . . ? C16 N2 C21 108.4(3) . . ? C15 N2 C21 112.5(3) . . ? C16 N2 H2 107.8 . . ? C15 N2 H2 107.8 . . ? C21 N2 H2 107.8 . . ? C2 C1 C6 117.6(3) . . ? C2 C1 H1 121.2 . . ? C6 C1 H1 121.2 . . ? O2 C2 C1 122.8(3) . . ? O2 C2 C3 116.1(3) . . ? C1 C2 C3 121.2(3) . . ? O3 C3 C4 124.7(3) . . ? O3 C3 C2 115.3(3) . . ? C4 C3 C2 119.9(3) . . ? C3 C4 C5 119.8(3) . . ? C3 C4 H4 120.1 . . ? C5 C4 H4 120.1 . . ? C6 C5 C4 119.9(3) . . ? C6 C5 C7 110.2(3) . . ? C4 C5 C7 129.6(3) . . ? C5 C6 C1 121.5(3) . . ? C5 C6 N1 110.3(3) . . ? C1 C6 N1 128.2(3) . . ? C5 C7 C8 103.3(2) . . ? C5 C7 C17 110.9(3) . . ? C8 C7 C17 111.0(3) . . ? C5 C7 C21 115.4(3) . . ? C8 C7 C21 114.3(3) . . ? C17 C7 C21 102.2(3) . . ? N1 C8 C18 105.5(2) . . ? N1 C8 C7 104.7(2) . . ? C18 C8 C7 117.9(3) . . ? N1 C8 H8 109.4 . . ? C18 C8 H8 109.4 . . ? C7 C8 H8 109.4 . . ? O4 C9 N1 123.8(3) . . ? O4 C9 C10 121.9(3) . . ? N1 C9 C10 114.3(3) . . ? C9 C10 C11 115.6(3) . . ? C9 C10 H10A 108.4 . . ? C11 C10 H10A 108.4 . . ? C9 C10 H10B 108.4 . . ? C11 C10 H10B 108.4 . . ? H10A C10 H10B 107.4 . . ? O1 C11 C18 115.2(3) . . ? O1 C11 C10 105.0(2) . . ? C18 C11 C10 109.7(2) . . ? O1 C11 H11 108.9 . . ? C18 C11 H11 108.9 . . ? C10 C11 H11 108.9 . . ? O1 C12 C13 110.2(3) . . ? O1 C12 H12A 109.6 . . ? C13 C12 H12A 109.6 . . ? O1 C12 H12B 109.6 . . ? C13 C12 H12B 109.6 . . ? H12A C12 H12B 108.1 . . ? C14 C13 C12 121.2(3) . . ? C14 C13 H13 119.4 . . ? C12 C13 H13 119.4 . . ? C13 C14 C15 122.5(3) . . ? C13 C14 C19 122.0(3) . . ? C15 C14 C19 115.5(3) . . ? C14 C15 N2 110.8(3) . . ? C14 C15 H15A 109.5 . . ? N2 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? N2 C15 H15B 109.5 . . ? H15A C15 H15B 108.1 . . ? N2 C16 C17 104.3(3) . . ? 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 103.2(3) . . ? 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 . . ? C11 C18 C8 107.3(3) . . ? C11 C18 C19 118.5(3) . . ? C8 C18 C19 112.4(3) . . ? C11 C18 H18 105.9 . . ? C8 C18 H18 105.9 . . ? C19 C18 H18 105.9 . . ? C14 C19 C18 114.9(3) . . ? C14 C19 C20 109.5(3) . . ? C18 C19 C20 106.4(3) . . ? C14 C19 H19 108.7 . . ? C18 C19 H19 108.7 . . ? C20 C19 H19 108.7 . . ? C21 C20 C19 108.9(3) . . ? 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 N2 111.4(3) . . ? C20 C21 C7 114.9(3) . . ? N2 C21 C7 103.7(3) . . ? 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 . . ? H11W O1W H12W 92.0 . . ? 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 C251 N3 N3A C27 -122.9(8) . . . . ? C25 N3 N3A C27 -119.9(15) . . . . ? C27 N3 N3A C251 122.9(8) . . . . ? C25 N3 N3A C251 3.0(15) . . . . ? N3A N3 C25 C251 -3.5(18) . . . . ? C27 N3 C25 C251 -97.3(14) . . . . ? N3A N3 C25 O6A -104(2) . . . . ? C27 N3 C25 O6A 161.8(12) . . . . ? C251 N3 C25 O6A -100.8(10) . . . . ? N3A N3 C25 C261 -168(2) . . . . ? C27 N3 C25 C261 98(2) . . . . ? C251 N3 C25 C261 -164.3(17) . . . . ? N3A N3 C25 C26 136(3) . . . . ? C27 N3 C25 C26 42(3) . . . . ? C251 N3 C25 C26 139(2) . . . . ? N3A N3 C25 C241 39(2) . . . . ? C27 N3 C25 C241 -55.1(16) . . . . ? C251 N3 C25 C241 42.2(8) . . . . ? N3A N3 C25 C24 -56(2) . . . . ? C27 N3 C25 C24 -150.3(12) . . . . ? C251 N3 C25 C24 -52.9(6) . . . . ? O6A C25 C251 N3A 108.6(15) . . . . ? C261 C25 C251 N3A 111(7) . . . . ? C26 C25 C251 N3A -142(3) . . . . ? N3 C25 C251 N3A 1.6(8) . . . . ? C241 C25 C251 N3A -134.3(11) . . . . ? C24 C25 C251 N3A 121.7(10) . . . . ? O6A C25 C251 C26A -116(3) . . . . ? C261 C25 C251 C26A -113(7) . . . . ? C26 C25 C251 C26A -6(4) . . . . ? N3 C25 C251 C26A 137(2) . . . . ? C241 C25 C251 C26A 2(2) . . . . ? C24 C25 C251 C26A -103(2) . . . . ? O6A C25 C251 C26B -26(3) . . . . ? C261 C25 C251 C26B -24(7) . . . . ? C26 C25 C251 C26B 83(4) . . . . ? N3 C25 C251 C26B -133(3) . . . . ? C241 C25 C251 C26B 91(3) . . . . ? C24 C25 C251 C26B -13(2) . . . . ? O6A C25 C251 N3 107.0(15) . . . . ? C261 C25 C251 N3 109(7) . . . . ? C26 C25 C251 N3 -144(3) . . . . ? C241 C25 C251 N3 -135.9(10) . . . . ? C24 C25 C251 N3 120.1(9) . . . . ? O6A C25 C251 O61 -122.1(18) . . . . ? C261 C25 C251 O61 -120(7) . . . . ? C26 C25 C251 O61 -13(3) . . . . ? N3 C25 C251 O61 130.9(13) . . . . ? C241 C25 C251 O61 -5.0(15) . . . . ? C24 C25 C251 O61 -109.0(14) . . . . ? O6A C25 C251 O6 -19.9(19) . . . . ? C261 C25 C251 O6 -18(7) . . . . ? C26 C25 C251 O6 89(3) . . . . ? N3 C25 C251 O6 -126.9(13) . . . . ? C241 C25 C251 O6 97.2(15) . . . . ? C24 C25 C251 O6 -6.8(13) . . . . ? O6A C25 C251 C241 -117.1(16) . . . . ? C261 C25 C251 C241 -115(7) . . . . ? C26 C25 C251 C241 -8(3) . . . . ? N3 C25 C251 C241 135.9(10) . . . . ? C24 C25 C251 C241 -104.1(11) . . . . ? O6A C25 C251 C24 -13.0(15) . . . . ? C261 C25 C251 C24 -11(7) . . . . ? C26 C25 C251 C24 96(3) . . . . ? N3 C25 C251 C24 -120.1(9) . . . . ? C241 C25 C251 C24 104.1(11) . . . . ? N3 N3A C251 C25 -2.7(14) . . . . ? C27 N3A C251 C25 59.3(13) . . . . ? N3 N3A C251 C26A -160(2) . . . . ? C27 N3A C251 C26A -98(2) . . . . ? N3 N3A C251 C26B 142(2) . . . . ? C27 N3A C251 C26B -156(2) . . . . ? C27 N3A C251 N3 62.0(13) . . . . ? N3 N3A C251 O61 -124.5(16) . . . . ? C27 N3A C251 O61 -62.5(18) . . . . ? N3 N3A C251 O6 118.5(15) . . . . ? C27 N3A C251 O6 -179.5(10) . . . . ? N3 N3A C251 C241 -67.0(19) . . . . ? C27 N3A C251 C241 -5(2) . . . . ? N3 N3A C251 C24 63.8(16) . . . . ? C27 N3A C251 C24 125.8(11) . . . . ? N3A N3 C251 C25 177.1(15) . . . . ? C27 N3 C251 C25 115.4(9) . . . . ? C27 N3 C251 N3A -61.7(14) . . . . ? C25 N3 C251 N3A -177.1(15) . . . . ? N3A N3 C251 C26A 28(3) . . . . ? C27 N3 C251 C26A -33(3) . . . . ? C25 N3 C251 C26A -149(3) . . . . ? N3A N3 C251 C26B -56(3) . . . . ? C27 N3 C251 C26B -118(2) . . . . ? C25 N3 C251 C26B 127(2) . . . . ? N3A N3 C251 O61 80.6(19) . . . . ? C27 N3 C251 O61 19.0(18) . . . . ? C25 N3 C251 O61 -96.5(14) . . . . ? N3A N3 C251 O6 -85.6(19) . . . . ? C27 N3 C251 O6 -147.3(12) . . . . ? C25 N3 C251 O6 97.3(13) . . . . ? N3A N3 C251 C241 132.6(15) . . . . ? C27 N3 C251 C241 71.0(13) . . . . ? C25 N3 C251 C241 -44.4(9) . . . . ? N3A N3 C251 C24 -128.6(14) . . . . ? C27 N3 C251 C24 169.8(8) . . . . ? C25 N3 C251 C24 54.3(6) . . . . ? N3A N3 C27 O8 -125.6(15) . . . . ? C251 N3 C27 O8 -64.1(12) . . . . ? C25 N3 C27 O8 -1.8(17) . . . . ? C251 N3 C27 N3A 61.5(17) . . . . ? C25 N3 C27 N3A 124(2) . . . . ? N3A N3 C27 C28 68.7(18) . . . . ? C251 N3 C27 C28 130.2(8) . . . . ? C25 N3 C27 C28 -167.5(9) . . . . ? N3 N3A C27 O8 74.7(19) . . . . ? C251 N3A C27 O8 11.9(19) . . . . ? C251 N3A C27 N3 -62.9(14) . . . . ? N3 N3A C27 C28 -125.9(14) . . . . ? C251 N3A C27 C28 171.2(10) . . . . ? O8 C27 C28 C33 -162.0(6) . . . . ? N3 C27 C28 C33 2.9(11) . . . . ? N3A C27 C28 C33 36.1(10) . . . . ? O8 C27 C28 C29 15.1(9) . . . . ? N3 C27 C28 C29 -179.9(9) . . . . ? N3A C27 C28 C29 -146.7(8) . . . . ? C33 C28 C29 C30 0.5(6) . . . . ? C27 C28 C29 C30 -176.8(4) . . . . ? C28 C29 C30 C31 0.6(6) . . . . ? C29 C30 C31 C32 -1.5(6) . . . . ? C29 C30 C31 N4 178.9(4) . . . . ? O9 N4 C31 C32 163.6(5) . . . . ? O10 N4 C31 C32 -14.3(6) . . . . ? O9 N4 C31 C30 -16.8(6) . . . . ? O10 N4 C31 C30 165.3(4) . . . . ? C30 C31 C32 C33 1.2(7) . . . . ? N4 C31 C32 C33 -179.3(4) . . . . ? C31 C32 C33 C28 0.0(7) . . . . ? C29 C28 C33 C32 -0.8(7) . . . . ? C27 C28 C33 C32 176.3(5) . . . . ? C25 C251 O6 C24 8.7(16) . . . . ? N3A C251 O6 C24 -106.4(16) . . . . ? C26A C251 O6 C24 155(2) . . . . ? C26B C251 O6 C24 176(6) . . . . ? N3 C251 O6 C24 -67(2) . . . . ? O61 C251 O6 C24 122.8(14) . . . . ? C241 C251 O6 C24 77.7(14) . . . . ? C25 C251 O6 O5A 58.5(18) . . . . ? N3A C251 O6 O5A -56.7(17) . . . . ? C26A C251 O6 O5A -155(2) . . . . ? C26B C251 O6 O5A -134(6) . . . . ? N3 C251 O6 O5A -17(2) . . . . ? O61 C251 O6 O5A 172.6(15) . . . . ? C241 C251 O6 O5A 127.5(16) . . . . ? C24 C251 O6 O5A 49.8(12) . . . . ? C25 C251 O6 O7A -109.3(14) . . . . ? N3A C251 O6 O7A 135.6(18) . . . . ? C26A C251 O6 O7A 37(2) . . . . ? C26B C251 O6 O7A 58(5) . . . . ? N3 C251 O6 O7A 175.1(16) . . . . ? O61 C251 O6 O7A 4.9(17) . . . . ? C241 C251 O6 O7A -40.3(16) . . . . ? C24 C251 O6 O7A -118(2) . . . . ? C25 C251 O6 C26A -146(2) . . . . ? N3A C251 O6 C26A 99(2) . . . . ? C26B C251 O6 C26A 21(6) . . . . ? N3 C251 O6 C26A 138(2) . . . . ? O61 C251 O6 C26A -32.0(19) . . . . ? C241 C251 O6 C26A -77(2) . . . . ? C24 C251 O6 C26A -155(2) . . . . ? O7A O6 O5A C24 77(7) . . . . ? C251 O6 O5A C24 -61.1(15) . . . . ? C26A O6 O5A C24 -88(3) . . . . ? C24 O6 O5A O3W 7(3) . . . . ? O7A O6 O5A O3W 84(8) . . . . ? C251 O6 O5A O3W -55(3) . . . . ? C26A O6 O5A O3W -81(4) . . . . ? O3W O5 O6A C24 -94(2) . . . . ? C24 O5 O6A O3W 94(2) . . . . ? C24 O5 O6A C25 -35(2) . . . . ? O3W O5 O6A C25 -129(3) . . . . ? C24 O5 O6A C26 -91.8(18) . . . . ? O3W O5 O6A C26 174(2) . . . . ? C251 C25 O6A C24 16.1(19) . . . . ? C261 C25 O6A C24 -163(3) . . . . ? C26 C25 O6A C24 -128(2) . . . . ? N3 C25 O6A C24 81.4(16) . . . . ? C241 C25 O6A C24 -57(2) . . . . ? C251 C25 O6A O5 47(3) . . . . ? C261 C25 O6A O5 -133(4) . . . . ? C26 C25 O6A O5 -97(3) . . . . ? N3 C25 O6A O5 112(3) . . . . ? C241 C25 O6A O5 -26(4) . . . . ? C24 C25 O6A O5 31(2) . . . . ? C251 C25 O6A O3W -64(2) . . . . ? C261 C25 O6A O3W 117(3) . . . . ? C26 C25 O6A O3W 152(2) . . . . ? N3 C25 O6A O3W 1(2) . . . . ? C241 C25 O6A O3W -137(2) . . . . ? C24 C25 O6A O3W -80(2) . . . . ? C251 C25 O6A C26 143.9(17) . . . . ? C261 C25 O6A C26 -35(3) . . . . ? N3 C25 O6A C26 -150.8(17) . . . . ? C241 C25 O6A C26 71.2(17) . . . . ? C24 C25 O6A C26 128(2) . . . . ? O6 O5A C24 O6A 169(2) . . . . ? O3W O5A C24 O6A -6(2) . . . . ? O6 O5A C24 O5 -128.3(16) . . . . ? O3W O5A C24 O5 56.7(16) . . . . ? O3W O5A C24 O6 -174.9(19) . . . . ? O6 O5A C24 C251 59.8(14) . . . . ? O3W O5A C24 C251 -115.1(13) . . . . ? O6 O5A C24 C25 107.1(17) . . . . ? O3W O5A C24 C25 -67.8(19) . . . . ? O6 O5A C24 O3W 174.9(19) . . . . ? O5 O6A C24 O5A 90(3) . . . . ? O3W O6A C24 O5A 7(3) . . . . ? C25 O6A C24 O5A -118(2) . . . . ? C26 O6A C24 O5A -155(2) . . . . ? O3W O6A C24 O5 -83(2) . . . . ? C25 O6A C24 O5 152(2) . . . . ? C26 O6A C24 O5 114(3) . . . . ? O5 O6A C24 O6 168(12) . . . . ? O3W O6A C24 O6 85(12) . . . . ? C25 O6A C24 O6 -41(13) . . . . ? C26 O6A C24 O6 -78(13) . . . . ? O5 O6A C24 C251 -164.8(19) . . . . ? O3W O6A C24 C251 112.2(18) . . . . ? C25 O6A C24 C251 -13.0(15) . . . . ? C26 O6A C24 C251 -50(2) . . . . ? O5 O6A C24 C25 -152(2) . . . . ? O3W O6A C24 C25 125(2) . . . . ? C26 O6A C24 C25 -37.4(14) . . . . ? O5 O6A C24 O3W 83(2) . . . . ? C25 O6A C24 O3W -125(2) . . . . ? C26 O6A C24 O3W -163(3) . . . . ? O6A O5 C24 O5A -105(3) . . . . ? O3W O5 C24 O5A -54(2) . . . . ? O3W O5 C24 O6A 51.5(18) . . . . ? O6A O5 C24 O6 -177(3) . . . . ? O3W O5 C24 O6 -126(2) . . . . ? O6A O5 C24 C251 50(5) . . . . ? O3W O5 C24 C251 102(5) . . . . ? O6A O5 C24 C25 26(2) . . . . ? O3W O5 C24 C25 77.1(14) . . . . ? O6A O5 C24 O3W -51.5(18) . . . . ? O7A O6 C24 O5A -159(3) . . . . ? C251 O6 C24 O5A 110(2) . . . . ? C26A O6 C24 O5A 130(3) . . . . ? O5A O6 C24 O6A -81(13) . . . . ? O7A O6 C24 O6A 120(12) . . . . ? C251 O6 C24 O6A 30(12) . . . . ? C26A O6 C24 O6A 50(13) . . . . ? O5A O6 C24 O5 85(3) . . . . ? O7A O6 C24 O5 -74(3) . . . . ? C251 O6 C24 O5 -165(2) . . . . ? C26A O6 C24 O5 -144(2) . . . . ? O5A O6 C24 C251 -110(2) . . . . ? O7A O6 C24 C251 90.6(18) . . . . ? C26A O6 C24 C251 20.2(17) . . . . ? O5A O6 C24 C25 -118(2) . . . . ? O7A O6 C24 C25 83(2) . . . . ? C251 O6 C24 C25 -7.4(14) . . . . ? C26A O6 C24 C25 13(3) . . . . ? O5A O6 C24 O3W -6(2) . . . . ? O7A O6 C24 O3W -165.3(16) . . . . ? C251 O6 C24 O3W 104.1(17) . . . . ? C26A O6 C24 O3W 124(2) . . . . ? C25 C251 C24 O5A 125(2) . . . . ? N3A C251 C24 O5A 40(2) . . . . ? C26A C251 C24 O5A -91(3) . . . . ? C26B C251 C24 O5A -65(3) . . . . ? N3 C251 C24 O5A 71(2) . . . . ? O61 C251 C24 O5A -132(2) . . . . ? O6 C251 C24 O5A -64(2) . . . . ? C241 C251 C24 O5A -173(2) . . . . ? C25 C251 C24 O6A 14.4(17) . . . . ? N3A C251 C24 O6A -70(2) . . . . ? C26A C251 C24 O6A 158(3) . . . . ? C26B C251 C24 O6A -176(3) . . . . ? N3 C251 C24 O6A -40.1(19) . . . . ? O61 C251 C24 O6A 117(2) . . . . ? O6 C251 C24 O6A -175(3) . . . . ? C241 C251 C24 O6A 76.4(19) . . . . ? C25 C251 C24 O5 -30(4) . . . . ? N3A C251 C24 O5 -115(4) . . . . ? C26A C251 C24 O5 114(5) . . . . ? C26B C251 C24 O5 140(5) . . . . ? N3 C251 C24 O5 -84(5) . . . . ? O61 C251 C24 O5 73(5) . . . . ? O6 C251 C24 O5 141(5) . . . . ? C241 C251 C24 O5 32(5) . . . . ? C25 C251 C24 O6 -171.1(17) . . . . ? N3A C251 C24 O6 104.1(19) . . . . ? C26A C251 C24 O6 -27(3) . . . . ? C26B C251 C24 O6 -2(3) . . . . ? N3 C251 C24 O6 134.4(17) . . . . ? O61 C251 C24 O6 -68.1(18) . . . . ? C241 C251 C24 O6 -109.1(17) . . . . ? N3A C251 C24 C25 -84.8(12) . . . . ? C26A C251 C24 C25 144(2) . . . . ? C26B C251 C24 C25 169.5(19) . . . . ? N3 C251 C24 C25 -54.5(8) . . . . ? O61 C251 C24 C25 103.0(10) . . . . ? O6 C251 C24 C25 171.1(17) . . . . ? C241 C251 C24 C25 62.0(6) . . . . ? C25 C251 C24 O3W 62.5(11) . . . . ? N3A C251 C24 O3W -22.3(16) . . . . ? C26A C251 C24 O3W -154(2) . . . . ? C26B C251 C24 O3W -128(2) . . . . ? N3 C251 C24 O3W 8.0(13) . . . . ? O61 C251 C24 O3W 165.5(13) . . . . ? O6 C251 C24 O3W -126.4(19) . . . . ? C241 C251 C24 O3W 124.5(12) . . . . ? C251 C25 C24 O5A -73(2) . . . . ? O6A C25 C24 O5A 91(3) . . . . ? C261 C25 C24 O5A 105(3) . . . . ? C26 C25 C24 O5A 149(2) . . . . ? N3 C25 C24 O5A -23(2) . . . . ? C241 C25 C24 O5A -134(2) . . . . ? C251 C25 C24 O6A -163(2) . . . . ? C261 C25 C24 O6A 14(2) . . . . ? C26 C25 C24 O6A 59(2) . . . . ? N3 C25 C24 O6A -114.0(19) . . . . ? C241 C25 C24 O6A 135.2(19) . . . . ? C251 C25 C24 O5 169.6(18) . . . . ? O6A C25 C24 O5 -27(2) . . . . ? C261 C25 C24 O5 -13(2) . . . . ? C26 C25 C24 O5 32(2) . . . . ? N3 C25 C24 O5 -140.9(17) . . . . ? C241 C25 C24 O5 108.2(17) . . . . ? C251 C25 C24 O6 8.9(17) . . . . ? O6A C25 C24 O6 172(3) . . . . ? C261 C25 C24 O6 -174(2) . . . . ? C26 C25 C24 O6 -129(2) . . . . ? N3 C25 C24 O6 58.3(19) . . . . ? C241 C25 C24 O6 -52.5(18) . . . . ? O6A C25 C24 C251 163(2) . . . . ? C261 C25 C24 C251 177.4(15) . . . . ? C26 C25 C24 C251 -137.9(14) . . . . ? N3 C25 C24 C251 49.4(9) . . . . ? C241 C25 C24 C251 -61.4(6) . . . . ? C251 C25 C24 O3W -127.4(11) . . . . ? O6A C25 C24 O3W 36.1(19) . . . . ? C261 C25 C24 O3W 50.1(17) . . . . ? C26 C25 C24 O3W 94.7(15) . . . . ? N3 C25 C24 O3W -77.9(11) . . . . ? C241 C25 C24 O3W 171.2(10) . . . . ? C251 C25 C26 O7 23(5) . . . . ? O6A C25 C26 O7 141(3) . . . . ? C261 C25 C26 O7 -176(5) . . . . ? N3 C25 C26 O7 -91(3) . . . . ? C241 C25 C26 O7 16(2) . . . . ? C24 C25 C26 O7 102(3) . . . . ? C251 C25 C26 O6A -118(2) . . . . ? C261 C25 C26 O6A 43(3) . . . . ? N3 C25 C26 O6A 128(2) . . . . ? C241 C25 C26 O6A -125.0(13) . . . . ? C24 C25 C26 O6A -39.3(11) . . . . ? C24 O6A C26 C25 52.4(19) . . . . ? O5 O6A C26 C25 115.6(15) . . . . ? O3W O6A C26 C25 -79(6) . . . . ? C24 O6A C26 O7 -29(5) . . . . ? O5 O6A C26 O7 34(4) . . . . ? O3W O6A C26 O7 -160(5) . . . . ? C25 O6A C26 O7 -81(4) . . . . ? C24 O6 O7A C26A -102(2) . . . . ? O5A O6 O7A C26A -168(7) . . . . ? C251 O6 O7A C26A -30.5(18) . . . . ? C25 C251 C26A O7A 75(3) . . . . ? N3A C251 C26A O7A -150.3(18) . . . . ? C26B C251 C26A O7A -40(2) . . . . ? N3 C251 C26A O7A -165.9(14) . . . . ? O61 C251 C26A O7A 85(3) . . . . ? O6 C251 C26A O7A -31.1(19) . . . . ? C241 C251 C26A O7A 77(2) . . . . ? C24 C251 C26A O7A -11(3) . . . . ? C25 C251 C26A O6 106(2) . . . . ? N3A C251 C26A O6 -119.2(13) . . . . ? C26B C251 C26A O6 -9(2) . . . . ? N3 C251 C26A O6 -135(2) . . . . ? O61 C251 C26A O6 117(3) . . . . ? C241 C251 C26A O6 107.7(14) . . . . ? C24 C251 C26A O6 20.0(18) . . . . ? O6 O7A C26A C251 34(2) . . . . ? C24 O6 C26A C251 -25(2) . . . . ? O5A O6 C26A C251 36(3) . . . . ? O7A O6 C26A C251 -138(3) . . . . ? C24 O6 C26A O7A 113(3) . . . . ? O5A O6 C26A O7A 175(3) . . . . ? C251 O6 C26A O7A 138(3) . . . . ? C25 C251 O61 O6B 32(3) . . . . ? N3A C251 O61 O6B 148(3) . . . . ? C26A C251 O61 O6B -142(5) . . . . ? C26B C251 O61 O6B -99(3) . . . . ? N3 C251 O61 O6B 109(3) . . . . ? O6 C251 O61 O6B -82(3) . . . . ? C241 C251 O61 O6B 26(2) . . . . ? C24 C251 O61 O6B -40(3) . . . . ? C25 C251 O61 C241 6.3(19) . . . . ? N3A C251 O61 C241 122.0(16) . . . . ? C26A C251 O61 C241 -168(3) . . . . ? C26B C251 O61 C241 -125(2) . . . . ? N3 C251 O61 C241 83(2) . . . . ? O6 C251 O61 C241 -107.6(17) . . . . ? C24 C251 O61 C241 -65.7(18) . . . . ? C25 C251 O61 C26B 131.5(16) . . . . ? N3A C251 O61 C26B -112.8(18) . . . . ? C26A C251 O61 C26B -43(3) . . . . ? N3 C251 O61 C26B -152(2) . . . . ? O6 C251 O61 C26B 17.5(16) . . . . ? C241 C251 O61 C26B 125(2) . . . . ? C24 C251 O61 C26B 59.4(15) . . . . ? O6B O51 O5B C241 -20(4) . . . . ? C241 O51 O5B O31W -163(5) . . . . ? O6B O51 O5B O31W 177(3) . . . . ? C251 O61 O6B C241 -27(3) . . . . ? C26B O61 O6B C241 -83.0(19) . . . . ? C241 O61 O6B O51 -16(3) . . . . ? C251 O61 O6B O51 -43(4) . . . . ? C26B O61 O6B O51 -99(3) . . . . ? O5B O51 O6B O61 42(6) . . . . ? C241 O51 O6B O61 18(3) . . . . ? O5B O51 O6B C241 24(5) . . . . ? O6B O51 C241 O5B 159(4) . . . . ? O5B O51 C241 O6B -159(4) . . . . ? O5B O51 C241 O61 -177(4) . . . . ? O6B O51 C241 O61 -18(3) . . . . ? O5B O51 C241 C251 -12(15) . . . . ? O6B O51 C241 C251 147(13) . . . . ? O5B O51 C241 C25 5(5) . . . . ? O6B O51 C241 C25 165(3) . . . . ? O31W O5B C241 O51 150(9) . . . . ? O51 O5B C241 O6B 20(4) . . . . ? O31W O5B C241 O6B 170(6) . . . . ? O51 O5B C241 O61 6(9) . . . . ? O31W O5B C241 O61 156(6) . . . . ? O51 O5B C241 C251 177(4) . . . . ? O31W O5B C241 C251 -33(8) . . . . ? O51 O5B C241 C25 -175(4) . . . . ? O31W O5B C241 C25 -25(6) . . . . ? O61 O6B C241 O51 -162(3) . . . . ? O61 O6B C241 O5B -173(3) . . . . ? O51 O6B C241 O5B -11(2) . . . . ? O51 O6B C241 O61 162(3) . . . . ? O61 O6B C241 C251 24(2) . . . . ? O51 O6B C241 C251 -174(3) . . . . ? O61 O6B C241 C25 62(5) . . . . ? O51 O6B C241 C25 -136(6) . . . . ? O6B O61 C241 O51 21(3) . . . . ? C251 O61 C241 O51 177(3) . . . . ? C26B O61 C241 O51 140(3) . . . . ? O6B O61 C241 O5B 17(7) . . . . ? C251 O61 C241 O5B 173(7) . . . . ? C26B O61 C241 O5B 137(7) . . . . ? C251 O61 C241 O6B 156(2) . . . . ? C26B O61 C241 O6B 119(3) . . . . ? O6B O61 C241 C251 -156(2) . . . . ? C26B O61 C241 C251 -36.8(12) . . . . ? O6B O61 C241 C25 -162(2) . . . . ? C251 O61 C241 C25 -5.5(16) . . . . ? C26B O61 C241 C25 -42(2) . . . . ? C25 C251 C241 O51 20(13) . . . . ? N3A C251 C241 O51 98(13) . . . . ? C26A C251 C241 O51 -159(13) . . . . ? C26B C251 C241 O51 -109(13) . . . . ? N3 C251 C241 O51 64(13) . . . . ? O61 C251 C241 O51 -167(14) . . . . ? O6 C251 C241 O51 -87(13) . . . . ? C24 C251 C241 O51 -42(13) . . . . ? C25 C251 C241 O5B 10(3) . . . . ? N3A C251 C241 O5B 89(3) . . . . ? C26A C251 C241 O5B -169(3) . . . . ? C26B C251 C241 O5B -119(3) . . . . ? N3 C251 C241 O5B 55(3) . . . . ? O61 C251 C241 O5B -176(4) . . . . ? O6 C251 C241 O5B -96(3) . . . . ? C24 C251 C241 O5B -52(3) . . . . ? C25 C251 C241 O6B 165(2) . . . . ? N3A C251 C241 O6B -117(2) . . . . ? C26A C251 C241 O6B -14(2) . . . . ? C26B C251 C241 O6B 36(3) . . . . ? N3 C251 C241 O6B -150(2) . . . . ? O61 C251 C241 O6B -22(2) . . . . ? O6 C251 C241 O6B 58(2) . . . . ? C24 C251 C241 O6B 103(2) . . . . ? C25 C251 C241 O61 -173.5(19) . . . . ? N3A C251 C241 O61 -95(2) . . . . ? C26A C251 C241 O61 7(2) . . . . ? C26B C251 C241 O61 57(2) . . . . ? N3 C251 C241 O61 -129.0(18) . . . . ? O6 C251 C241 O61 79.8(18) . . . . ? C24 C251 C241 O61 124.4(18) . . . . ? N3A C251 C241 C25 78.2(15) . . . . ? C26A C251 C241 C25 -179.2(12) . . . . ? C26B C251 C241 C25 -129.2(17) . . . . ? N3 C251 C241 C25 44.5(10) . . . . ? O61 C251 C241 C25 173.5(19) . . . . ? O6 C251 C241 C25 -106.7(7) . . . . ? C24 C251 C241 C25 -62.0(6) . . . . ? C251 C25 C241 O51 -176(3) . . . . ? O6A C25 C241 O51 -76(3) . . . . ? C261 C25 C241 O51 -10(3) . . . . ? C26 C25 C241 O51 -1(3) . . . . ? N3 C25 C241 O51 144(2) . . . . ? C24 C25 C241 O51 -114(2) . . . . ? C251 C25 C241 O5B -173(2) . . . . ? O6A C25 C241 O5B -73(2) . . . . ? C261 C25 C241 O5B -7(3) . . . . ? C26 C25 C241 O5B 2(2) . . . . ? N3 C25 C241 O5B 147.1(17) . . . . ? C24 C25 C241 O5B -111.4(18) . . . . ? C251 C25 C241 O6B -46(5) . . . . ? O6A C25 C241 O6B 54(5) . . . . ? C261 C25 C241 O6B 119(5) . . . . ? C26 C25 C241 O6B 129(6) . . . . ? N3 C25 C241 O6B -86(5) . . . . ? C24 C25 C241 O6B 15(5) . . . . ? C251 C25 C241 O61 6.5(19) . . . . ? O6A C25 C241 O61 106(2) . . . . ? C261 C25 C241 O61 172(3) . . . . ? C26 C25 C241 O61 -179(3) . . . . ? N3 C25 C241 O61 -33(2) . . . . ? C24 C25 C241 O61 68(2) . . . . ? O6A C25 C241 C251 99.7(12) . . . . ? C261 C25 C241 C251 165.6(19) . . . . ? C26 C25 C241 C251 174.9(19) . . . . ? N3 C25 C241 C251 -39.9(9) . . . . ? C24 C25 C241 C251 61.6(6) . . . . ? C251 C25 C261 O71 -31(8) . . . . ? O6A C25 C261 O71 -29(2) . . . . ? C26 C25 C261 O71 -153(4) . . . . ? N3 C25 C261 O71 70(3) . . . . ? C241 C25 C261 O71 -139.4(17) . . . . ? C24 C25 C261 O71 -41(2) . . . . ? C25 C251 C26B O7B 140.9(18) . . . . ? N3A C251 C26B O7B 11(3) . . . . ? C26A C251 C26B O7B -80(3) . . . . ? N3 C251 C26B O7B 41(4) . . . . ? O61 C251 C26B O7B -109(3) . . . . ? O6 C251 C26B O7B 125(7) . . . . ? C241 C251 C26B O7B -147(2) . . . . ? C24 C251 C26B O7B 128(3) . . . . ? C25 C251 C26B O61 -109.8(19) . . . . ? N3A C251 C26B O61 120.6(15) . . . . ? C26A C251 C26B O61 29(2) . . . . ? N3 C251 C26B O61 151(2) . . . . ? O6 C251 C26B O61 -126(6) . . . . ? C241 C251 C26B O61 -37.9(11) . . . . ? C24 C251 C26B O61 -122.7(13) . . . . ? O31W O7B C26B C251 -55(5) 4_645 . . . ? O31W O7B C26B O61 -114(4) 4_645 . . . ? O6B O61 C26B C251 112.7(14) . . . . ? C241 O61 C26B C251 50.0(16) . . . . ? O6B O61 C26B O7B -150(2) . . . . ? C241 O61 C26B O7B 148(2) . . . . ? C251 O61 C26B O7B 98(2) . . . . ? C24 O6A O3W O5A -5(2) . . . . ? O5 O6A O3W O5A -64.6(17) . . . . ? C25 O6A O3W O5A 67(2) . . . . ? C26 O6A O3W O5A 128(5) . . . . ? C24 O6A O3W O5 59.2(10) . . . . ? C25 O6A O3W O5 131.4(16) . . . . ? C26 O6A O3W O5 -168(6) . . . . ? O5 O6A O3W C24 -59.2(10) . . . . ? C25 O6A O3W C24 72.2(16) . . . . ? C26 O6A O3W C24 133(6) . . . . ? C24 O5A O3W O6A 6(2) . . . . ? O6 O5A O3W O6A 0(4) . . . . ? C24 O5A O3W O5 -40.1(13) . . . . ? O6 O5A O3W O5 -46(3) . . . . ? O6 O5A O3W C24 -6(2) . . . . ? C24 O5 O3W O6A -63.6(14) . . . . ? C24 O5 O3W O5A 40.7(13) . . . . ? O6A O5 O3W O5A 104.4(19) . . . . ? O6A O5 O3W C24 63.6(14) . . . . ? O5A C24 O3W O6A -172(3) . . . . ? O5 C24 O3W O6A 73(2) . . . . ? O6 C24 O3W O6A -165(3) . . . . ? C251 C24 O3W O6A -86(2) . . . . ? C25 C24 O3W O6A -43(2) . . . . ? O6A C24 O3W O5A 172(3) . . . . ? O5 C24 O3W O5A -115(2) . . . . ? O6 C24 O3W O5A 6(2) . . . . ? C251 C24 O3W O5A 86(2) . . . . ? C25 C24 O3W O5A 128(2) . . . . ? O5A C24 O3W O5 115(2) . . . . ? O6A C24 O3W O5 -73(2) . . . . ? O6 C24 O3W O5 122(2) . . . . ? C251 C24 O3W O5 -158.8(15) . . . . ? C25 C24 O3W O5 -116.4(13) . . . . ? O51 O5B O31W O7B 6(8) . . . 4_655 ? C241 O5B O31W O7B -136(6) . . . 4_655 ? C22 O2 C2 C1 9.5(5) . . . . ? C22 O2 C2 C3 -170.4(3) . . . . ? C6 C1 C2 O2 -178.6(3) . . . . ? C6 C1 C2 C3 1.3(5) . . . . ? C23 O3 C3 C4 -3.2(5) . . . . ? C23 O3 C3 C2 177.1(3) . . . . ? O2 C2 C3 O3 -3.2(5) . . . . ? C1 C2 C3 O3 176.9(3) . . . . ? O2 C2 C3 C4 177.1(3) . . . . ? C1 C2 C3 C4 -2.8(5) . . . . ? O3 C3 C4 C5 -178.2(3) . . . . ? C2 C3 C4 C5 1.4(5) . . . . ? C3 C4 C5 C6 1.3(5) . . . . ? C3 C4 C5 C7 -172.1(3) . . . . ? C4 C5 C6 C1 -2.8(5) . . . . ? C7 C5 C6 C1 171.8(3) . . . . ? C4 C5 C6 N1 179.1(3) . . . . ? C7 C5 C6 N1 -6.4(4) . . . . ? C2 C1 C6 C5 1.4(5) . . . . ? C2 C1 C6 N1 179.2(3) . . . . ? C9 N1 C6 C5 -158.0(3) . . . . ? C8 N1 C6 C5 -4.0(4) . . . . ? C9 N1 C6 C1 24.0(5) . . . . ? C8 N1 C6 C1 178.0(3) . . . . ? C6 C5 C7 C8 13.5(3) . . . . ? C4 C5 C7 C8 -172.6(3) . . . . ? C6 C5 C7 C17 -105.5(3) . . . . ? C4 C5 C7 C17 68.4(4) . . . . ? C6 C5 C7 C21 138.9(3) . . . . ? C4 C5 C7 C21 -47.2(5) . . . . ? C9 N1 C8 C18 43.4(3) . . . . ? C6 N1 C8 C18 -112.9(3) . . . . ? C9 N1 C8 C7 168.5(3) . . . . ? C6 N1 C8 C7 12.2(3) . . . . ? C5 C7 C8 N1 -15.1(3) . . . . ? C17 C7 C8 N1 103.9(3) . . . . ? C21 C7 C8 N1 -141.2(3) . . . . ? C5 C7 C8 C18 101.8(3) . . . . ? C17 C7 C8 C18 -139.2(3) . . . . ? C21 C7 C8 C18 -24.3(4) . . . . ? C6 N1 C9 O4 -16.6(5) . . . . ? C8 N1 C9 O4 -168.3(3) . . . . ? C6 N1 C9 C10 165.8(3) . . . . ? C8 N1 C9 C10 14.1(4) . . . . ? O4 C9 C10 C11 136.9(3) . . . . ? N1 C9 C10 C11 -45.4(4) . . . . ? C12 O1 C11 C18 -66.5(4) . . . . ? C12 O1 C11 C10 172.7(3) . . . . ? C9 C10 C11 O1 138.4(3) . . . . ? C9 C10 C11 C18 14.0(4) . . . . ? C11 O1 C12 C13 91.8(3) . . . . ? O1 C12 C13 C14 -68.2(4) . . . . ? C12 C13 C14 C15 177.6(4) . . . . ? C12 C13 C14 C19 -2.8(6) . . . . ? C13 C14 C15 N2 -127.6(4) . . . . ? C19 C14 C15 N2 52.8(5) . . . . ? C16 N2 C15 C14 75.6(4) . . . . ? C21 N2 C15 C14 -47.1(4) . . . . ? C15 N2 C16 C17 -142.2(3) . . . . ? C21 N2 C16 C17 -17.2(4) . . . . ? N2 C16 C17 C7 37.2(4) . . . . ? C5 C7 C17 C16 -166.3(3) . . . . ? C8 C7 C17 C16 79.5(3) . . . . ? C21 C7 C17 C16 -42.8(3) . . . . ? O1 C11 C18 C8 -76.0(3) . . . . ? C10 C11 C18 C8 42.2(3) . . . . ? O1 C11 C18 C19 52.6(4) . . . . ? C10 C11 C18 C19 170.8(3) . . . . ? N1 C8 C18 C11 -72.5(3) . . . . ? C7 C8 C18 C11 171.0(2) . . . . ? N1 C8 C18 C19 155.5(2) . . . . ? C7 C8 C18 C19 39.0(4) . . . . ? C13 C14 C19 C18 59.8(5) . . . . ? C15 C14 C19 C18 -120.6(3) . . . . ? C13 C14 C19 C20 179.4(3) . . . . ? C15 C14 C19 C20 -1.0(4) . . . . ? C11 C18 C19 C14 -64.8(4) . . . . ? C8 C18 C19 C14 61.3(4) . . . . ? C11 C18 C19 C20 173.9(3) . . . . ? C8 C18 C19 C20 -60.0(3) . . . . ? C14 C19 C20 C21 -55.5(4) . . . . ? C18 C19 C20 C21 69.2(3) . . . . ? C19 C20 C21 N2 60.8(4) . . . . ? C19 C20 C21 C7 -56.8(4) . . . . ? C16 N2 C21 C20 -133.5(3) . . . . ? C15 N2 C21 C20 -8.7(4) . . . . ? C16 N2 C21 C7 -9.3(4) . . . . ? C15 N2 C21 C7 115.5(3) . . . . ? C5 C7 C21 C20 -86.1(3) . . . . ? C8 C7 C21 C20 33.4(4) . . . . ? C17 C7 C21 C20 153.4(3) . . . . ? C5 C7 C21 N2 152.0(3) . . . . ? C8 C7 C21 N2 -88.5(3) . . . . ? C17 C7 C21 N2 31.5(3) . . . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 29.00 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.531 _refine_diff_density_min -0.425 _refine_diff_density_rms 0.079 # start Validation Reply Form _vrf_PLAT771_2 ; PROBLEM: Suspect N-H Bond in CIF: N3 -- H3A .. 1.47 Ang. RESPONSE: N3 and H3A belong to the different part of disordered anion ; _vrf_PLAT780_2 ; PROBLEM: Coordinates do not Form a Properly Connected Set ? RESPONSE: Anion and water molecules reveal high degree of disorder. Some of hydrogen atoms are missing ; # end Validation Reply Form #==== end data_2 _database_code_depnum_ccdc_archive 'CCDC 758143' #TrackingRef 'bialonska1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; brucinium N-(4-nitrobenzoyl)-D-serinate trihydrate ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C23 H27 N2 O4, C10 H9 N2 O6, 3(H2 O)' _chemical_formula_sum 'C33 H42 N4 O13' _chemical_formula_weight 702.71 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 12.559(2) _cell_length_b 7.069(2) _cell_length_c 35.388(4) _cell_angle_alpha 90.00 _cell_angle_beta 92.13(3) _cell_angle_gamma 90.00 _cell_volume 3139.6(11) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 10423 _cell_measurement_theta_min 3.10 _cell_measurement_theta_max 37.90 _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.487 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1488 _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 45471 _diffrn_reflns_av_R_equivalents 0.0531 _diffrn_reflns_av_sigmaI/netI 0.0538 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -47 _diffrn_reflns_limit_l_max 51 _diffrn_reflns_theta_min 3.10 _diffrn_reflns_theta_max 31.00 _reflns_number_total 10585 _reflns_number_gt 8539 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET) (compiled May 8 2007,13:10:02) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET) (compiled May 8 2007,13:10:02) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET) (compiled May 8 2007,13:10:02) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0434P)^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 10585 _refine_ls_number_parameters 901 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0550 _refine_ls_R_factor_gt 0.0405 _refine_ls_wR_factor_ref 0.0837 _refine_ls_wR_factor_gt 0.0803 _refine_ls_goodness_of_fit_ref 1.003 _refine_ls_restrained_S_all 1.003 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.24199(10) 0.3923(2) 0.95022(4) 0.0158(3) Uani 1 1 d . . . O2 O 0.93032(11) 0.5226(3) 0.95107(4) 0.0219(3) Uani 1 1 d . . . O3 O 0.94021(11) 0.4698(2) 0.87889(4) 0.0184(3) Uani 1 1 d . . . O4 O 0.56326(11) 0.4453(3) 1.01343(4) 0.0202(3) Uani 1 1 d . . . N1 N 0.54499(12) 0.3826(2) 0.95103(5) 0.0129(3) Uani 1 1 d . . . N2 N 0.43346(13) 0.3281(3) 0.82846(5) 0.0133(3) Uani 1 1 d . . . H2 H 0.4540 0.3157 0.8036 0.016 Uiso 1 1 calc R . . C1 C 0.74101(15) 0.4542(3) 0.95611(5) 0.0148(4) Uani 1 1 d . . . H1 H 0.7422 0.4668 0.9828 0.018 Uiso 1 1 calc R . . C2 C 0.83538(15) 0.4779(3) 0.93539(6) 0.0167(4) Uani 1 1 d . . . C3 C 0.84071(15) 0.4542(3) 0.89585(6) 0.0156(4) Uani 1 1 d . . . C4 C 0.74852(15) 0.4173(3) 0.87670(6) 0.0151(4) Uani 1 1 d . . . H4 H 0.7467 0.4029 0.8500 0.018 Uiso 1 1 calc R . . C5 C 0.65270(15) 0.3999(3) 0.89746(5) 0.0129(4) Uani 1 1 d . . . C6 C 0.65023(15) 0.4134(3) 0.93637(5) 0.0131(4) Uani 1 1 d . . . C7 C 0.54470(15) 0.3478(3) 0.88330(5) 0.0122(4) Uani 1 1 d . . . C8 C 0.47101(15) 0.3735(3) 0.91934(5) 0.0115(4) Uani 1 1 d . . . H8 H 0.4246 0.2595 0.9218 0.014 Uiso 1 1 calc R . . C9 C 0.50582(15) 0.4241(3) 0.98613(5) 0.0148(4) Uani 1 1 d . . . C10 C 0.38596(15) 0.4398(3) 0.99042(5) 0.0159(4) Uani 1 1 d . . . H10A H 0.3571 0.3119 0.9951 0.019 Uiso 1 1 calc R . . H10B H 0.3725 0.5180 1.0130 0.019 Uiso 1 1 calc R . . C11 C 0.32656(16) 0.5240(3) 0.95700(5) 0.0147(4) Uani 1 1 d . . . H11 H 0.2962 0.6491 0.9643 0.018 Uiso 1 1 calc R . . C12 C 0.16521(16) 0.4571(4) 0.92368(6) 0.0198(4) Uani 1 1 d . . . H12A H 0.1585 0.5963 0.9255 0.024 Uiso 1 1 calc R . . H12B H 0.0952 0.4001 0.9287 0.024 Uiso 1 1 calc R . . C13 C 0.19900(16) 0.4018(3) 0.88399(6) 0.0172(4) Uani 1 1 d . . . H13 H 0.1553 0.3140 0.8703 0.021 Uiso 1 1 calc R . . C14 C 0.28659(15) 0.4685(3) 0.86691(5) 0.0146(4) Uani 1 1 d . . . C15 C 0.32062(15) 0.4034(3) 0.82808(6) 0.0158(4) Uani 1 1 d . . . H15A H 0.2713 0.3031 0.8187 0.019 Uiso 1 1 calc R . . H15B H 0.3146 0.5110 0.8102 0.019 Uiso 1 1 calc R . . C16 C 0.43916(17) 0.1366(3) 0.84701(6) 0.0154(4) Uani 1 1 d . . . H16A H 0.3790 0.1176 0.8639 0.018 Uiso 1 1 calc R . . H16B H 0.4387 0.0342 0.8279 0.018 Uiso 1 1 calc R . . C17 C 0.54128(16) 0.1433(3) 0.86857(6) 0.0149(4) Uani 1 1 d . . . H17A H 0.6017 0.1172 0.8521 0.018 Uiso 1 1 calc R . . H17B H 0.5427 0.0514 0.8897 0.018 Uiso 1 1 calc R . . C18 C 0.40319(16) 0.5524(3) 0.92273(5) 0.0130(4) Uani 1 1 d . . . H18 H 0.4541 0.6543 0.9310 0.016 Uiso 1 1 calc R . . C19 C 0.35875(16) 0.6138(3) 0.88481(6) 0.0140(4) Uani 1 1 d . . . H19 H 0.3186 0.7347 0.8877 0.017 Uiso 1 1 calc R . . C20 C 0.45509(17) 0.6478(3) 0.85790(6) 0.0161(4) Uani 1 1 d . . . H20A H 0.4284 0.7085 0.8342 0.019 Uiso 1 1 calc R . . H20B H 0.5074 0.7343 0.8704 0.019 Uiso 1 1 calc R . . C21 C 0.50923(15) 0.4622(3) 0.84875(5) 0.0125(4) Uani 1 1 d . . . H21 H 0.5717 0.4870 0.8328 0.015 Uiso 1 1 calc R . . C22 C 0.92906(18) 0.5517(4) 0.99107(6) 0.0252(5) Uani 1 1 d . . . H22A H 1.0010 0.5839 1.0007 0.038 Uiso 1 1 calc R . . H22B H 0.9051 0.4358 1.0034 0.038 Uiso 1 1 calc R . . H22C H 0.8802 0.6555 0.9965 0.038 Uiso 1 1 calc R . . C23 C 0.94737(16) 0.4283(4) 0.83954(5) 0.0188(4) Uani 1 1 d . . . H23A H 1.0211 0.4455 0.8320 0.028 Uiso 1 1 calc R . . H23B H 0.9005 0.5139 0.8248 0.028 Uiso 1 1 calc R . . H23C H 0.9254 0.2972 0.8348 0.028 Uiso 1 1 calc R . . O1A O -0.26176(11) 0.3357(2) 0.54924(4) 0.0162(3) Uani 1 1 d . . . O2A O 0.43479(11) 0.4282(3) 0.54751(4) 0.0211(3) Uani 1 1 d . . . O3A O 0.42404(10) 0.4481(2) 0.62010(4) 0.0174(3) Uani 1 1 d . . . O4A O 0.07767(11) 0.3248(2) 0.48764(4) 0.0175(3) Uani 1 1 d . . . N1A N 0.04151(12) 0.4297(3) 0.54759(4) 0.0127(3) Uani 1 1 d . . . N2A N -0.10257(13) 0.5244(3) 0.66774(5) 0.0138(3) Uani 1 1 d . . . H2A H -0.0808 0.5587 0.6922 0.017 Uiso 1 1 calc R . . C1A C 0.24245(15) 0.4256(3) 0.54249(5) 0.0148(4) Uani 1 1 d . . . H1A H 0.2421 0.4112 0.5158 0.018 Uiso 1 1 calc R . . C2A C 0.33410(15) 0.4351(3) 0.56324(6) 0.0154(4) Uani 1 1 d . . . C3A C 0.32813(15) 0.4507(3) 0.60290(5) 0.0143(4) Uani 1 1 d . . . C4A C 0.23001(15) 0.4689(3) 0.62179(5) 0.0136(4) Uani 1 1 d . . . H4A H 0.2297 0.4845 0.6484 0.016 Uiso 1 1 calc R . . C5A C 0.13824(15) 0.4635(3) 0.60109(5) 0.0130(4) Uani 1 1 d . . . C6A C 0.14512(15) 0.4380(3) 0.56233(5) 0.0126(4) Uani 1 1 d . . . C7A C 0.02388(15) 0.4980(3) 0.61407(5) 0.0114(4) Uani 1 1 d . . . C8A C -0.03932(14) 0.4355(3) 0.57925(5) 0.0113(4) Uani 1 1 d . . . H8A H -0.0945 0.5334 0.5728 0.014 Uiso 1 1 calc R . . C9A C 0.01355(16) 0.3555(3) 0.51391(5) 0.0134(4) Uani 1 1 d . . . C10A C -0.10473(16) 0.3224(3) 0.51081(5) 0.0142(4) Uani 1 1 d . . . H10C H -0.1191 0.2396 0.4886 0.017 Uiso 1 1 calc R . . H10D H -0.1391 0.4456 0.5050 0.017 Uiso 1 1 calc R . . C11A C -0.16339(15) 0.2324(3) 0.54556(6) 0.0137(4) Uani 1 1 d . . . H11A H -0.1803 0.0970 0.5398 0.016 Uiso 1 1 calc R . . C12A C -0.33542(16) 0.2598(3) 0.57777(6) 0.0185(4) Uani 1 1 d . . . H12C H -0.4101 0.2809 0.5688 0.022 Uiso 1 1 calc R . . H12D H -0.3243 0.1218 0.5806 0.022 Uiso 1 1 calc R . . C13A C -0.31699(16) 0.3531(3) 0.61508(6) 0.0173(4) Uani 1 1 d . . . H13A H -0.3701 0.4324 0.6251 0.021 Uiso 1 1 calc R . . C14A C -0.22826(16) 0.3253(3) 0.63355(6) 0.0148(4) Uani 1 1 d . . . C15A C -0.20864(15) 0.4248(3) 0.67008(5) 0.0156(4) Uani 1 1 d . . . H15C H -0.2065 0.3331 0.6912 0.019 Uiso 1 1 calc R . . H15D H -0.2660 0.5176 0.6743 0.019 Uiso 1 1 calc R . . C16A C -0.10551(16) 0.7027(3) 0.64400(6) 0.0146(4) Uani 1 1 d . . . H16C H -0.1121 0.8158 0.6603 0.018 Uiso 1 1 calc R . . H16D H -0.1668 0.6998 0.6256 0.018 Uiso 1 1 calc R . . C17A C 0.00200(16) 0.7077(3) 0.62299(6) 0.0134(4) Uani 1 1 d . . . H17C H -0.0051 0.7833 0.5995 0.016 Uiso 1 1 calc R . . H17D H 0.0599 0.7618 0.6394 0.016 Uiso 1 1 calc R . . C18A C -0.09282(15) 0.2417(3) 0.57994(5) 0.0121(4) Uani 1 1 d . . . H18A H -0.0350 0.1472 0.5761 0.015 Uiso 1 1 calc R . . C19A C -0.14103(16) 0.1916(3) 0.61930(6) 0.0139(4) Uani 1 1 d . . . H19A H -0.1700 0.0598 0.6181 0.017 Uiso 1 1 calc R . . C20A C -0.04882(16) 0.1964(3) 0.64676(6) 0.0145(4) Uani 1 1 d . . . H20C H 0.0097 0.1170 0.6375 0.017 Uiso 1 1 calc R . . H20D H -0.0700 0.1459 0.6715 0.017 Uiso 1 1 calc R . . C21A C -0.01161(15) 0.3987(3) 0.65127(5) 0.0132(4) Uani 1 1 d . . . H21A H 0.0504 0.4001 0.6698 0.016 Uiso 1 1 calc R . . C22A C 0.44454(18) 0.4298(5) 0.50719(6) 0.0327(6) Uani 1 1 d . . . H22D H 0.5200 0.4244 0.5012 0.049 Uiso 1 1 calc R . . H22E H 0.4129 0.5461 0.4967 0.049 Uiso 1 1 calc R . . H22F H 0.4074 0.3199 0.4961 0.049 Uiso 1 1 calc R . . C23A C 0.42049(16) 0.4818(3) 0.65990(5) 0.0170(4) Uani 1 1 d . . . H23D H 0.4929 0.4783 0.6712 0.026 Uiso 1 1 calc R . . H23E H 0.3772 0.3840 0.6715 0.026 Uiso 1 1 calc R . . H23F H 0.3889 0.6063 0.6643 0.026 Uiso 1 1 calc R . . O5 O 0.59382(12) 0.3093(2) 0.76762(4) 0.0215(3) Uani 1 1 d . . . O6 O 0.76618(12) 0.2571(2) 0.77798(5) 0.0242(4) Uani 1 1 d . . . O7 O 0.57653(13) -0.1518(2) 0.78953(4) 0.0244(3) Uani 1 1 d . . . H7 H 0.5299 -0.2236 0.7759 0.037 Uiso 1 1 d R . . O8 O 0.68411(12) -0.1434(3) 0.67297(4) 0.0264(4) Uani 1 1 d . . . O9 O 0.29935(13) -0.0626(3) 0.54210(4) 0.0337(4) Uani 1 1 d . . . O10 O 0.17931(12) -0.0094(3) 0.58621(5) 0.0262(4) Uani 1 1 d . . . N3 N 0.58904(13) 0.0260(3) 0.71610(5) 0.0156(3) Uani 1 1 d . . . H3 H 0.5283 0.0798 0.7215 0.019 Uiso 1 1 calc R . . N4 N 0.27154(14) -0.0407(3) 0.57530(5) 0.0207(4) Uani 1 1 d . . . C24 C 0.67764(17) 0.2154(3) 0.76395(6) 0.0167(4) Uani 1 1 d . . . C25 C 0.67656(16) 0.0298(3) 0.74178(6) 0.0161(4) Uani 1 1 d . . . H25 H 0.7431 0.0230 0.7272 0.019 Uiso 1 1 calc R . . C26 C 0.67324(17) -0.1417(3) 0.76778(6) 0.0206(5) Uani 1 1 d . . . H26A H 0.6785 -0.2579 0.7524 0.025 Uiso 1 1 calc R . . H26B H 0.7360 -0.1380 0.7856 0.025 Uiso 1 1 calc R . . C27 C 0.60074(15) -0.0632(3) 0.68271(5) 0.0157(4) Uani 1 1 d . . . C28 C 0.50997(15) -0.0572(3) 0.65610(5) 0.0143(4) Uani 1 1 d . . . C29 C 0.53282(16) -0.1160(3) 0.61912(6) 0.0164(4) Uani 1 1 d . . . H29 H 0.6023 -0.1572 0.6133 0.020 Uiso 1 1 calc R . . C30 C 0.45466(17) -0.1123(3) 0.59262(6) 0.0178(4) Uani 1 1 d . . . H30 H 0.4663 -0.1505 0.5674 0.021 Uiso 1 1 calc R . . C31 C 0.35448(16) -0.0496(3) 0.60362(6) 0.0168(4) Uani 1 1 d . . . C32 C 0.32808(16) 0.0053(3) 0.64052(6) 0.0160(4) Uani 1 1 d . . . H32 H 0.2579 0.0430 0.6463 0.019 Uiso 1 1 calc R . . C33 C 0.40712(16) 0.0014(3) 0.66679(6) 0.0158(4) Uani 1 1 d . . . H33 H 0.3948 0.0370 0.6921 0.019 Uiso 1 1 calc R . . O5A O 0.25231(12) 0.4277(2) 0.72724(4) 0.0227(3) Uani 1 1 d . . . O6A O 0.08838(12) 0.4146(2) 0.75427(4) 0.0233(3) Uani 1 1 d . . . O7A O 0.04868(12) 0.8031(2) 0.70744(4) 0.0208(3) Uani 1 1 d . . . H7A H 0.0122 0.8709 0.7207 0.031 Uiso 1 1 d R . . O8A O 0.22271(11) 0.9515(3) 0.81451(4) 0.0237(3) Uani 1 1 d . . . O9A O -0.16067(13) 1.0000(3) 0.96048(4) 0.0302(4) Uani 1 1 d . . . O10A O -0.28203(12) 0.9477(3) 0.91989(4) 0.0313(4) Uani 1 1 d . . . N3A N 0.10924(13) 0.7623(3) 0.78383(5) 0.0161(4) Uani 1 1 d . . . H3A H 0.0452 0.7116 0.7834 0.019 Uiso 1 1 calc R . . N4A N -0.18878(14) 0.9667(3) 0.92832(5) 0.0212(4) Uani 1 1 d . . . C24A C 0.17274(16) 0.4986(3) 0.74441(6) 0.0164(4) Uani 1 1 d . . . C25A C 0.18077(16) 0.7108(3) 0.75265(6) 0.0153(4) Uani 1 1 d . . . H25A H 0.2557 0.7388 0.7614 0.018 Uiso 1 1 calc R . . C26A C 0.15623(17) 0.8271(3) 0.71754(6) 0.0189(4) Uani 1 1 d . . . H26C H 0.1715 0.9623 0.7226 0.023 Uiso 1 1 calc R . . H26D H 0.2010 0.7848 0.6967 0.023 Uiso 1 1 calc R . . C27A C 0.13448(16) 0.8779(3) 0.81200(5) 0.0154(4) Uani 1 1 d . . . C28A C 0.04772(15) 0.9068(3) 0.84182(5) 0.0142(4) Uani 1 1 d . . . C29A C 0.07717(16) 0.9362(3) 0.87887(5) 0.0169(4) Uani 1 1 d . . . H29A H 0.1508 0.9433 0.8859 0.020 Uiso 1 1 calc R . . C30A C -0.00030(16) 0.9566(3) 0.90745(6) 0.0191(4) Uani 1 1 d . . . H30A H 0.0224 0.9755 0.9331 0.023 Uiso 1 1 calc R . . C31A C -0.10572(16) 0.9489(3) 0.89793(5) 0.0162(4) Uani 1 1 d . . . C32A C -0.13755(16) 0.9230(3) 0.86142(6) 0.0185(4) Uani 1 1 d . . . H32A H -0.2113 0.9183 0.8545 0.022 Uiso 1 1 calc R . . C33A C -0.05951(16) 0.9025(3) 0.83307(6) 0.0171(4) Uani 1 1 d . . . H33A H -0.0829 0.8853 0.8075 0.021 Uiso 1 1 calc R . . O1W O -0.04591(13) 0.1034(2) 0.74512(5) 0.0246(4) Uani 1 1 d . . . H11W H -0.1029 0.1440 0.7552 0.037 Uiso 1 1 d R . . H12W H 0.0031 0.1873 0.7484 0.037 Uiso 1 1 d R . . O2W O -0.11291(13) 0.5658(2) 0.74807(4) 0.0226(3) Uani 1 1 d . . . H21W H -0.1590 0.4942 0.7584 0.034 Uiso 1 1 d R . . H22W H -0.0523 0.5090 0.7486 0.034 Uiso 1 1 d R . . O3W O 0.27383(12) -0.0003(2) 0.93571(4) 0.0247(4) Uani 1 1 d . . . H31W H 0.2666 0.1192 0.9393 0.037 Uiso 1 1 d R . . H32W H 0.3317 -0.0374 0.9472 0.037 Uiso 1 1 d R . . O4W O 0.45213(13) 0.5883(3) 0.74946(5) 0.0287(4) Uani 1 1 d . . . H41W H 0.4985 0.4987 0.7499 0.043 Uiso 1 1 d R . . H42W H 0.3935 0.5457 0.7395 0.043 Uiso 1 1 d R . . O5W O 0.35869(12) 0.1238(2) 0.75650(4) 0.0217(3) Uani 1 1 d . . . H51W H 0.3223 0.0623 0.7725 0.033 Uiso 1 1 d R . . H52W H 0.3179 0.2080 0.7461 0.033 Uiso 1 1 d R . . O6W O 0.26206(13) 0.2467(3) 0.44187(5) 0.0253(4) Uani 1 1 d . . . H61W H 0.2083 0.2785 0.4548 0.038 Uiso 1 1 d R . . H62W H 0.2726 0.1272 0.4446 0.038 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 0.0106(6) 0.0184(8) 0.0180(7) 0.0020(6) -0.0035(5) -0.0005(6) O2 0.0108(7) 0.0390(10) 0.0155(7) -0.0049(7) -0.0034(6) -0.0027(7) O3 0.0111(6) 0.0295(9) 0.0145(7) -0.0014(6) 0.0000(5) -0.0006(6) O4 0.0143(7) 0.0325(9) 0.0135(7) -0.0003(7) -0.0046(5) 0.0003(7) N1 0.0095(7) 0.0154(9) 0.0136(8) 0.0006(6) -0.0023(6) -0.0008(6) N2 0.0146(8) 0.0130(8) 0.0121(8) -0.0019(6) -0.0031(6) 0.0007(7) C1 0.0120(8) 0.0183(10) 0.0141(9) -0.0005(8) -0.0003(7) 0.0008(8) C2 0.0107(9) 0.0199(11) 0.0193(10) 0.0007(8) -0.0029(8) -0.0002(8) C3 0.0109(8) 0.0178(10) 0.0182(9) -0.0003(8) 0.0024(7) 0.0002(8) C4 0.0144(9) 0.0169(10) 0.0137(9) -0.0016(8) -0.0013(7) 0.0011(8) C5 0.0111(8) 0.0131(10) 0.0144(9) -0.0011(7) -0.0020(7) 0.0004(7) C6 0.0127(8) 0.0122(10) 0.0145(9) 0.0004(7) 0.0028(7) 0.0003(8) C7 0.0097(8) 0.0135(10) 0.0131(9) -0.0016(7) -0.0013(7) -0.0013(7) C8 0.0102(8) 0.0134(10) 0.0107(9) -0.0010(7) -0.0028(7) -0.0007(7) C9 0.0138(9) 0.0152(10) 0.0155(9) 0.0015(8) 0.0003(7) -0.0009(8) C10 0.0122(8) 0.0227(11) 0.0128(9) 0.0005(8) 0.0005(7) -0.0014(8) C11 0.0130(9) 0.0157(10) 0.0154(9) -0.0012(8) 0.0009(8) 0.0004(8) C12 0.0117(9) 0.0282(12) 0.0190(10) 0.0011(9) -0.0047(8) 0.0029(9) C13 0.0149(9) 0.0192(11) 0.0172(10) 0.0000(8) -0.0048(8) 0.0054(8) C14 0.0150(9) 0.0133(10) 0.0152(9) -0.0006(8) -0.0048(7) 0.0053(8) C15 0.0138(9) 0.0166(10) 0.0165(9) -0.0022(8) -0.0053(7) 0.0030(8) C16 0.0157(10) 0.0101(9) 0.0200(10) -0.0007(8) -0.0036(8) 0.0002(8) C17 0.0121(9) 0.0134(10) 0.0190(10) -0.0032(8) -0.0035(8) 0.0024(8) C18 0.0142(9) 0.0123(9) 0.0124(9) -0.0003(7) -0.0018(7) 0.0000(8) C19 0.0152(9) 0.0113(9) 0.0152(9) -0.0006(7) -0.0007(8) 0.0027(8) C20 0.0219(11) 0.0105(10) 0.0158(10) 0.0011(8) -0.0001(8) -0.0001(8) C21 0.0118(8) 0.0119(9) 0.0139(9) -0.0015(7) -0.0007(7) -0.0024(7) C22 0.0169(10) 0.0432(15) 0.0152(10) -0.0023(10) -0.0048(9) -0.0022(10) C23 0.0154(9) 0.0271(12) 0.0143(9) -0.0002(9) 0.0035(8) 0.0013(9) O1A 0.0104(6) 0.0207(8) 0.0175(7) 0.0026(6) -0.0007(5) 0.0003(6) O2A 0.0103(6) 0.0387(10) 0.0145(7) -0.0005(7) 0.0011(5) 0.0011(7) O3A 0.0101(6) 0.0271(8) 0.0145(7) -0.0007(6) -0.0037(5) 0.0015(6) O4A 0.0159(7) 0.0219(8) 0.0147(7) -0.0028(6) 0.0006(6) -0.0014(6) N1A 0.0099(7) 0.0140(9) 0.0142(7) -0.0002(7) -0.0001(6) 0.0002(7) N2A 0.0127(8) 0.0147(8) 0.0139(8) 0.0007(7) -0.0015(6) 0.0016(7) C1A 0.0140(9) 0.0186(11) 0.0119(9) 0.0013(8) -0.0001(7) 0.0000(8) C2A 0.0120(8) 0.0164(10) 0.0180(9) 0.0002(8) 0.0021(7) 0.0003(8) C3A 0.0110(8) 0.0148(10) 0.0169(9) 0.0003(8) -0.0027(7) 0.0010(8) C4A 0.0140(9) 0.0130(10) 0.0137(9) -0.0001(8) 0.0006(7) -0.0018(8) C5A 0.0112(8) 0.0110(9) 0.0170(9) 0.0000(8) 0.0022(7) 0.0001(7) C6A 0.0118(8) 0.0113(9) 0.0144(9) 0.0003(8) -0.0022(7) 0.0003(8) C7A 0.0097(8) 0.0129(10) 0.0115(8) 0.0003(7) -0.0004(7) -0.0007(7) C8A 0.0093(8) 0.0130(9) 0.0117(8) 0.0004(7) 0.0010(7) 0.0006(7) C9A 0.0145(9) 0.0117(9) 0.0139(9) 0.0000(7) -0.0011(7) 0.0004(8) C10A 0.0134(9) 0.0160(10) 0.0132(9) -0.0024(8) -0.0015(7) -0.0001(8) C11A 0.0129(9) 0.0114(10) 0.0166(10) -0.0021(7) -0.0016(8) 0.0020(8) C12A 0.0129(9) 0.0242(11) 0.0185(10) 0.0022(9) -0.0006(8) -0.0031(9) C13A 0.0122(9) 0.0188(11) 0.0211(10) 0.0023(8) 0.0030(8) -0.0004(8) C14A 0.0148(9) 0.0129(10) 0.0167(10) 0.0027(8) 0.0029(8) -0.0013(8) C15A 0.0121(8) 0.0172(10) 0.0178(9) 0.0015(8) 0.0032(7) -0.0007(8) C16A 0.0153(9) 0.0114(10) 0.0171(10) 0.0016(8) -0.0003(8) 0.0022(8) C17A 0.0126(9) 0.0134(10) 0.0142(9) 0.0006(8) 0.0001(7) 0.0010(8) C18A 0.0111(9) 0.0105(9) 0.0147(9) -0.0015(7) 0.0002(7) 0.0008(7) C19A 0.0137(9) 0.0128(10) 0.0150(9) 0.0034(8) -0.0019(8) -0.0001(8) C20A 0.0155(9) 0.0124(10) 0.0155(10) 0.0011(8) -0.0019(8) 0.0007(8) C21A 0.0119(8) 0.0145(10) 0.0130(9) -0.0006(7) -0.0008(7) 0.0022(8) C22A 0.0172(10) 0.066(2) 0.0156(10) 0.0004(12) 0.0053(8) -0.0026(12) C23A 0.0139(9) 0.0220(11) 0.0149(9) -0.0029(8) -0.0017(7) -0.0001(8) O5 0.0190(8) 0.0198(8) 0.0256(8) -0.0032(6) 0.0002(6) 0.0027(6) O6 0.0190(8) 0.0269(9) 0.0261(8) -0.0057(7) -0.0057(7) -0.0050(7) O7 0.0274(8) 0.0245(9) 0.0214(8) -0.0016(7) 0.0032(7) -0.0037(7) O8 0.0192(8) 0.0382(10) 0.0214(8) -0.0091(7) -0.0035(6) 0.0107(7) O9 0.0254(8) 0.0566(13) 0.0183(8) -0.0062(9) -0.0086(7) -0.0014(9) O10 0.0166(7) 0.0325(10) 0.0289(8) 0.0018(7) -0.0040(6) -0.0027(7) N3 0.0119(8) 0.0182(9) 0.0165(8) -0.0026(7) -0.0020(6) 0.0022(7) N4 0.0193(9) 0.0218(10) 0.0204(9) -0.0003(8) -0.0054(7) -0.0035(8) C24 0.0167(10) 0.0186(11) 0.0149(10) 0.0007(8) 0.0006(8) -0.0025(8) C25 0.0120(9) 0.0208(11) 0.0154(9) -0.0021(8) -0.0013(8) 0.0001(8) C26 0.0189(10) 0.0195(11) 0.0230(11) -0.0002(9) -0.0037(9) 0.0017(9) C27 0.0146(9) 0.0167(10) 0.0157(9) 0.0001(8) -0.0006(7) 0.0004(8) C28 0.0163(9) 0.0116(9) 0.0148(9) 0.0005(8) -0.0013(7) 0.0001(8) C29 0.0152(9) 0.0166(10) 0.0174(10) -0.0006(8) 0.0013(8) -0.0013(8) C30 0.0221(10) 0.0177(11) 0.0137(9) -0.0015(8) 0.0021(8) -0.0032(9) C31 0.0169(9) 0.0170(10) 0.0160(9) 0.0016(8) -0.0044(8) -0.0044(9) C32 0.0134(9) 0.0153(10) 0.0194(10) 0.0007(8) 0.0008(8) -0.0003(8) C33 0.0181(10) 0.0163(10) 0.0131(9) -0.0017(8) 0.0013(8) 0.0014(8) O5A 0.0213(7) 0.0234(9) 0.0236(8) -0.0028(7) 0.0042(6) 0.0035(7) O6A 0.0179(7) 0.0184(8) 0.0335(9) -0.0012(7) 0.0000(6) -0.0027(6) O7A 0.0215(8) 0.0226(9) 0.0177(7) -0.0049(6) -0.0058(6) 0.0014(6) O8A 0.0161(7) 0.0345(10) 0.0206(7) -0.0071(7) 0.0005(6) -0.0084(7) O9A 0.0276(9) 0.0487(12) 0.0141(7) -0.0035(8) -0.0003(7) 0.0055(8) O10A 0.0174(7) 0.0538(12) 0.0225(8) 0.0041(9) -0.0011(6) 0.0074(8) N3A 0.0110(8) 0.0204(9) 0.0170(9) -0.0035(7) 0.0007(7) -0.0031(7) N4A 0.0199(9) 0.0267(11) 0.0169(9) 0.0033(8) 0.0012(7) 0.0058(8) C24A 0.0174(10) 0.0188(11) 0.0127(9) -0.0004(8) -0.0029(8) 0.0012(8) C25A 0.0123(9) 0.0184(11) 0.0154(10) -0.0017(8) 0.0011(8) -0.0011(8) C26A 0.0198(10) 0.0181(11) 0.0188(10) 0.0006(9) 0.0001(8) -0.0024(9) C27A 0.0173(9) 0.0164(10) 0.0122(9) 0.0021(8) -0.0025(8) 0.0003(8) C28A 0.0142(9) 0.0126(10) 0.0158(9) -0.0002(8) 0.0004(7) -0.0004(8) C29A 0.0157(9) 0.0199(11) 0.0149(9) -0.0002(8) -0.0029(7) 0.0001(9) C30A 0.0208(10) 0.0223(11) 0.0139(9) -0.0020(9) -0.0026(8) -0.0008(9) C31A 0.0165(9) 0.0172(10) 0.0153(9) 0.0010(8) 0.0045(7) 0.0028(8) C32A 0.0151(9) 0.0223(11) 0.0180(10) -0.0001(9) -0.0018(8) 0.0013(9) C33A 0.0173(9) 0.0218(11) 0.0121(9) -0.0008(8) -0.0024(8) 0.0028(9) O1W 0.0199(8) 0.0195(8) 0.0340(9) -0.0048(7) -0.0018(7) 0.0002(7) O2W 0.0209(8) 0.0230(9) 0.0236(8) 0.0016(7) -0.0025(6) -0.0007(7) O3W 0.0262(8) 0.0183(8) 0.0283(8) -0.0027(7) -0.0139(7) 0.0029(7) O4W 0.0218(8) 0.0261(9) 0.0377(10) -0.0040(8) -0.0056(7) 0.0020(7) O5W 0.0208(8) 0.0217(8) 0.0226(8) 0.0003(6) 0.0006(6) 0.0007(7) O6W 0.0256(8) 0.0215(9) 0.0292(9) -0.0021(7) 0.0066(7) -0.0037(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C12 1.398(2) . ? O1 C11 1.426(3) . ? O2 C2 1.334(2) . ? O2 C22 1.431(3) . ? O3 C3 1.411(2) . ? O3 C23 1.429(2) . ? O4 C9 1.193(2) . ? N1 C9 1.385(3) . ? N1 C8 1.431(2) . ? N1 C6 1.454(2) . ? N2 C16 1.505(3) . ? N2 C21 1.506(3) . ? N2 C15 1.514(3) . ? N2 H2 0.9300 . ? C1 C6 1.346(3) . ? C1 C2 1.426(3) . ? C1 H1 0.9500 . ? C2 C3 1.413(3) . ? C3 C4 1.345(3) . ? C4 C5 1.438(3) . ? C4 H4 0.9500 . ? C5 C6 1.382(3) . ? C5 C7 1.475(3) . ? C7 C21 1.518(3) . ? C7 C17 1.537(3) . ? C7 C8 1.614(3) . ? C8 C18 1.532(3) . ? C8 H8 1.0000 . ? C9 C10 1.523(3) . ? C10 C11 1.498(3) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C18 1.589(3) . ? C11 H11 1.0000 . ? C12 C13 1.533(3) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.359(3) . ? C13 H13 0.9500 . ? C14 C19 1.495(3) . ? C14 C15 1.525(3) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 C17 1.468(3) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 C19 1.498(3) . ? C18 H18 1.0000 . ? C19 C20 1.586(3) . ? C19 H19 1.0000 . ? C20 C21 1.519(3) . ? 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 . ? O1A C11A 1.445(2) . ? O1A C12A 1.494(3) . ? O2A C2A 1.401(2) . ? O2A C22A 1.437(3) . ? O3A C3A 1.329(2) . ? O3A C23A 1.431(2) . ? O4A C9A 1.271(2) . ? N1A C9A 1.337(3) . ? N1A C6A 1.385(2) . ? N1A C8A 1.540(2) . ? N2A C15A 1.512(3) . ? N2A C16A 1.515(3) . ? N2A C21A 1.576(3) . ? N2A H2A 0.9300 . ? C1A C2A 1.344(3) . ? C1A C6A 1.435(3) . ? C1A H1A 0.9500 . ? C2A C3A 1.413(3) . ? C3A C4A 1.429(3) . ? C4A C5A 1.343(3) . ? C4A H4A 0.9500 . ? C5A C6A 1.389(3) . ? C5A C7A 1.543(3) . ? C7A C8A 1.507(3) . ? C7A C17A 1.542(3) . ? C7A C21A 1.571(3) . ? C8A C18A 1.527(3) . ? C8A H8A 1.0000 . ? C9A C10A 1.504(3) . ? C10A C11A 1.590(3) . ? C10A H10C 0.9900 . ? C10A H10D 0.9900 . ? C11A C18A 1.480(3) . ? C11A H11A 1.0000 . ? C12A C13A 1.487(3) . ? C12A H12C 0.9900 . ? C12A H12D 0.9900 . ? C13A C14A 1.286(3) . ? C13A H13A 0.9500 . ? C14A C15A 1.484(3) . ? C14A C19A 1.545(3) . ? C15A H15C 0.9900 . ? C15A H15D 0.9900 . ? C16A C17A 1.566(3) . ? C16A H16C 0.9900 . ? C16A H16D 0.9900 . ? C17A H17C 0.9900 . ? C17A H17D 0.9900 . ? C18A C19A 1.579(3) . ? C18A H18A 1.0000 . ? C19A C20A 1.484(3) . ? C19A H19A 1.0000 . ? C20A C21A 1.511(3) . ? C20A H20C 0.9900 . ? C20A H20D 0.9900 . ? C21A H21A 1.0000 . ? C22A H22D 0.9800 . ? C22A H22E 0.9800 . ? C22A H22F 0.9800 . ? C23A H23D 0.9800 . ? C23A H23E 0.9800 . ? C23A H23F 0.9800 . ? O5 C24 1.255(3) . ? O6 C24 1.236(3) . ? O7 C26 1.464(3) . ? O7 H7 0.9024 . ? O8 C27 1.250(2) . ? O9 N4 1.248(2) . ? O10 N4 1.254(2) . ? N3 C27 1.352(3) . ? N3 C25 1.400(3) . ? N3 H3 0.8800 . ? N4 C31 1.420(3) . ? C24 C25 1.528(3) . ? C25 C26 1.524(3) . ? C25 H25 1.0000 . ? C26 H26A 0.9900 . ? C26 H26B 0.9900 . ? C27 C28 1.452(3) . ? C28 C29 1.413(3) . ? C28 C33 1.421(3) . ? C29 C30 1.332(3) . ? C29 H29 0.9500 . ? C30 C31 1.403(3) . ? C30 H30 0.9500 . ? C31 C32 1.414(3) . ? C32 C33 1.335(3) . ? C32 H32 0.9500 . ? C33 H33 0.9500 . ? O5A C24A 1.290(3) . ? O6A C24A 1.275(3) . ? O7A C26A 1.395(3) . ? O7A H7A 0.8215 . ? O8A C27A 1.224(3) . ? O9A N4A 1.202(2) . ? O10A N4A 1.205(2) . ? N3A C27A 1.319(3) . ? N3A C25A 1.494(3) . ? N3A H3A 0.8800 . ? N4A C31A 1.531(3) . ? C24A C25A 1.531(3) . ? C25A C26A 1.512(3) . ? C25A H25A 1.0000 . ? C26A H26C 0.9900 . ? C26A H26D 0.9900 . ? C27A C28A 1.558(3) . ? C28A C29A 1.365(3) . ? C28A C33A 1.371(3) . ? C29A C30A 1.437(3) . ? C29A H29A 0.9500 . ? C30A C31A 1.355(3) . ? C30A H30A 0.9500 . ? C31A C32A 1.351(3) . ? C32A C33A 1.436(3) . ? C32A H32A 0.9500 . ? C33A H33A 0.9500 . ? O1W H11W 0.8601 . ? O1W H12W 0.8600 . ? O2W H21W 0.8599 . ? O2W H22W 0.8600 . ? O3W H31W 0.8600 . ? O3W H32W 0.8601 . ? O4W H41W 0.8601 . ? O4W H42W 0.8599 . ? O5W H51W 0.8600 . ? O5W H52W 0.8599 . ? O6W H61W 0.8599 . ? O6W H62W 0.8600 . ? 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 112.94(17) . . ? C2 O2 C22 113.75(16) . . ? C3 O3 C23 119.18(15) . . ? C9 N1 C8 118.09(16) . . ? C9 N1 C6 130.26(16) . . ? C8 N1 C6 107.42(15) . . ? C16 N2 C21 109.82(15) . . ? C16 N2 C15 110.46(17) . . ? C21 N2 C15 110.95(16) . . ? C16 N2 H2 108.5 . . ? C21 N2 H2 108.5 . . ? C15 N2 H2 108.5 . . ? C6 C1 C2 117.54(18) . . ? C6 C1 H1 121.2 . . ? C2 C1 H1 121.2 . . ? O2 C2 C3 111.42(17) . . ? O2 C2 C1 124.11(18) . . ? C3 C2 C1 124.46(18) . . ? C4 C3 O3 124.07(18) . . ? C4 C3 C2 116.76(18) . . ? O3 C3 C2 119.17(17) . . ? C3 C4 C5 118.69(18) . . ? C3 C4 H4 120.7 . . ? C5 C4 H4 120.7 . . ? C6 C5 C4 123.59(17) . . ? C6 C5 C7 107.53(17) . . ? C4 C5 C7 128.61(17) . . ? C1 C6 C5 118.81(18) . . ? C1 C6 N1 127.63(17) . . ? C5 C6 N1 113.55(17) . . ? C5 C7 C21 112.29(17) . . ? C5 C7 C17 111.33(17) . . ? C21 C7 C17 102.94(16) . . ? C5 C7 C8 104.51(15) . . ? C21 C7 C8 114.62(16) . . ? C17 C7 C8 111.37(16) . . ? N1 C8 C18 104.39(16) . . ? N1 C8 C7 104.47(15) . . ? C18 C8 C7 119.46(16) . . ? N1 C8 H8 109.3 . . ? C18 C8 H8 109.3 . . ? C7 C8 H8 109.3 . . ? O4 C9 N1 121.91(18) . . ? O4 C9 C10 118.71(17) . . ? N1 C9 C10 119.37(17) . . ? C11 C10 C9 114.54(16) . . ? C11 C10 H10A 108.6 . . ? C9 C10 H10A 108.6 . . ? C11 C10 H10B 108.6 . . ? C9 C10 H10B 108.6 . . ? H10A C10 H10B 107.6 . . ? O1 C11 C10 102.67(17) . . ? O1 C11 C18 115.00(16) . . ? C10 C11 C18 110.78(16) . . ? O1 C11 H11 109.4 . . ? C10 C11 H11 109.4 . . ? C18 C11 H11 109.4 . . ? O1 C12 C13 108.94(17) . . ? O1 C12 H12A 109.9 . . ? C13 C12 H12A 109.9 . . ? O1 C12 H12B 109.9 . . ? C13 C12 H12B 109.9 . . ? H12A C12 H12B 108.3 . . ? C14 C13 C12 125.1(2) . . ? C14 C13 H13 117.4 . . ? C12 C13 H13 117.4 . . ? C13 C14 C19 122.55(18) . . ? C13 C14 C15 123.65(19) . . ? C19 C14 C15 113.80(17) . . ? N2 C15 C14 113.06(15) . . ? N2 C15 H15A 109.0 . . ? C14 C15 H15A 109.0 . . ? N2 C15 H15B 109.0 . . ? C14 C15 H15B 109.0 . . ? H15A C15 H15B 107.8 . . ? C17 C16 N2 102.95(17) . . ? C17 C16 H16A 111.2 . . ? N2 C16 H16A 111.2 . . ? C17 C16 H16B 111.2 . . ? N2 C16 H16B 111.2 . . ? H16A C16 H16B 109.1 . . ? C16 C17 C7 102.67(16) . . ? 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 . . ? C19 C18 C8 111.02(16) . . ? C19 C18 C11 120.27(17) . . ? C8 C18 C11 108.06(16) . . ? C19 C18 H18 105.4 . . ? C8 C18 H18 105.4 . . ? C11 C18 H18 105.4 . . ? C14 C19 C18 112.37(17) . . ? C14 C19 C20 108.30(16) . . ? C18 C19 C20 108.34(17) . . ? C14 C19 H19 109.3 . . ? C18 C19 H19 109.3 . . ? C20 C19 H19 109.3 . . ? C21 C20 C19 110.75(16) . . ? C21 C20 H20A 109.5 . . ? C19 C20 H20A 109.5 . . ? C21 C20 H20B 109.5 . . ? C19 C20 H20B 109.5 . . ? H20A C20 H20B 108.1 . . ? N2 C21 C7 102.13(16) . . ? N2 C21 C20 111.45(16) . . ? C7 C21 C20 114.13(16) . . ? N2 C21 H21 109.6 . . ? C7 C21 H21 109.6 . . ? C20 C21 H21 109.6 . . ? 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 . . ? C11A O1A C12A 115.62(16) . . ? C2A O2A C22A 120.37(16) . . ? C3A O3A C23A 112.80(15) . . ? C9A N1A C6A 124.35(17) . . ? C9A N1A C8A 120.03(16) . . ? C6A N1A C8A 111.12(15) . . ? C15A N2A C16A 114.50(15) . . ? C15A N2A C21A 114.20(16) . . ? C16A N2A C21A 105.49(14) . . ? C15A N2A H2A 107.4 . . ? C16A N2A H2A 107.4 . . ? C21A N2A H2A 107.4 . . ? C2A C1A C6A 117.22(17) . . ? C2A C1A H1A 121.4 . . ? C6A C1A H1A 121.4 . . ? C1A C2A O2A 123.27(18) . . ? C1A C2A C3A 118.09(18) . . ? O2A C2A C3A 118.64(17) . . ? O3A C3A C2A 111.91(16) . . ? O3A C3A C4A 124.71(17) . . ? C2A C3A C4A 123.38(17) . . ? C5A C4A C3A 118.67(18) . . ? C5A C4A H4A 120.7 . . ? C3A C4A H4A 120.7 . . ? C4A C5A C6A 117.29(17) . . ? C4A C5A C7A 128.49(18) . . ? C6A C5A C7A 114.02(16) . . ? N1A C6A C5A 106.57(16) . . ? N1A C6A C1A 128.21(17) . . ? C5A C6A C1A 125.21(17) . . ? C8A C7A C17A 110.90(16) . . ? C8A C7A C5A 100.24(15) . . ? C17A C7A C5A 112.82(16) . . ? C8A C7A C21A 113.39(16) . . ? C17A C7A C21A 101.51(15) . . ? C5A C7A C21A 118.35(16) . . ? C7A C8A C18A 117.95(16) . . ? C7A C8A N1A 105.14(14) . . ? C18A C8A N1A 106.88(16) . . ? C7A C8A H8A 108.8 . . ? C18A C8A H8A 108.8 . . ? N1A C8A H8A 108.8 . . ? O4A C9A N1A 124.50(18) . . ? O4A C9A C10A 124.82(18) . . ? N1A C9A C10A 110.62(17) . . ? C9A C10A C11A 119.39(17) . . ? C9A C10A H10C 107.5 . . ? C11A C10A H10C 107.5 . . ? C9A C10A H10D 107.5 . . ? C11A C10A H10D 107.5 . . ? H10C C10A H10D 107.0 . . ? O1A C11A C18A 113.05(16) . . ? O1A C11A C10A 106.85(16) . . ? C18A C11A C10A 109.74(16) . . ? O1A C11A H11A 109.0 . . ? C18A C11A H11A 109.0 . . ? C10A C11A H11A 109.0 . . ? C13A C12A O1A 111.16(17) . . ? C13A C12A H12C 109.4 . . ? O1A C12A H12C 109.4 . . ? C13A C12A H12D 109.4 . . ? O1A C12A H12D 109.4 . . ? H12C C12A H12D 108.0 . . ? C14A C13A C12A 119.1(2) . . ? C14A C13A H13A 120.4 . . ? C12A C13A H13A 120.4 . . ? C13A C14A C15A 118.9(2) . . ? C13A C14A C19A 122.64(19) . . ? C15A C14A C19A 118.51(17) . . ? C14A C15A N2A 106.93(16) . . ? C14A C15A H15C 110.3 . . ? N2A C15A H15C 110.3 . . ? C14A C15A H15D 110.3 . . ? N2A C15A H15D 110.3 . . ? H15C C15A H15D 108.6 . . ? N2A C16A C17A 106.16(16) . . ? N2A C16A H16C 110.5 . . ? C17A C16A H16C 110.5 . . ? N2A C16A H16D 110.5 . . ? C17A C16A H16D 110.5 . . ? H16C C16A H16D 108.7 . . ? C7A C17A C16A 103.84(16) . . ? C7A C17A H17C 111.0 . . ? C16A C17A H17C 111.0 . . ? C7A C17A H17D 111.0 . . ? C16A C17A H17D 111.0 . . ? H17C C17A H17D 109.0 . . ? C11A C18A C8A 106.07(16) . . ? C11A C18A C19A 118.53(16) . . ? C8A C18A C19A 113.50(16) . . ? C11A C18A H18A 105.9 . . ? C8A C18A H18A 105.9 . . ? C19A C18A H18A 105.9 . . ? C20A C19A C14A 108.51(17) . . ? C20A C19A C18A 104.88(16) . . ? C14A C19A C18A 116.76(17) . . ? C20A C19A H19A 108.8 . . ? C14A C19A H19A 108.8 . . ? C18A C19A H19A 108.8 . . ? C19A C20A C21A 108.76(17) . . ? C19A C20A H20C 109.9 . . ? C21A C20A H20C 109.9 . . ? C19A C20A H20D 109.9 . . ? C21A C20A H20D 109.9 . . ? H20C C20A H20D 108.3 . . ? C20A C21A C7A 115.52(17) . . ? C20A C21A N2A 110.30(16) . . ? C7A C21A N2A 106.88(15) . . ? C20A C21A H21A 108.0 . . ? C7A C21A H21A 108.0 . . ? N2A C21A H21A 108.0 . . ? O2A C22A H22D 109.5 . . ? O2A C22A H22E 109.5 . . ? H22D C22A H22E 109.5 . . ? O2A C22A H22F 109.5 . . ? H22D C22A H22F 109.5 . . ? H22E C22A H22F 109.5 . . ? O3A C23A H23D 109.5 . . ? O3A C23A H23E 109.5 . . ? H23D C23A H23E 109.5 . . ? O3A C23A H23F 109.5 . . ? H23D C23A H23F 109.5 . . ? H23E C23A H23F 109.5 . . ? C26 O7 H7 106.3 . . ? C27 N3 C25 117.92(17) . . ? C27 N3 H3 121.0 . . ? C25 N3 H3 121.0 . . ? O9 N4 O10 127.28(18) . . ? O9 N4 C31 115.81(17) . . ? O10 N4 C31 116.90(17) . . ? O6 C24 O5 125.3(2) . . ? O6 C24 C25 113.68(19) . . ? O5 C24 C25 121.03(19) . . ? N3 C25 C26 109.75(18) . . ? N3 C25 C24 109.99(18) . . ? C26 C25 C24 111.89(17) . . ? N3 C25 H25 108.4 . . ? C26 C25 H25 108.4 . . ? C24 C25 H25 108.4 . . ? O7 C26 C25 113.47(18) . . ? O7 C26 H26A 108.9 . . ? C25 C26 H26A 108.9 . . ? O7 C26 H26B 108.9 . . ? C25 C26 H26B 108.9 . . ? H26A C26 H26B 107.7 . . ? O8 C27 N3 124.85(18) . . ? O8 C27 C28 118.68(18) . . ? N3 C27 C28 116.42(17) . . ? C29 C28 C33 123.38(18) . . ? C29 C28 C27 114.24(17) . . ? C33 C28 C27 122.38(17) . . ? C30 C29 C28 118.46(19) . . ? C30 C29 H29 120.8 . . ? C28 C29 H29 120.8 . . ? C29 C30 C31 117.11(19) . . ? C29 C30 H30 121.4 . . ? C31 C30 H30 121.4 . . ? C30 C31 C32 125.93(18) . . ? C30 C31 N4 117.40(18) . . ? C32 C31 N4 116.67(18) . . ? C33 C32 C31 116.34(19) . . ? C33 C32 H32 121.8 . . ? C31 C32 H32 121.8 . . ? C32 C33 C28 118.72(19) . . ? C32 C33 H33 120.6 . . ? C28 C33 H33 120.6 . . ? C26A O7A H7A 109.7 . . ? C27A N3A C25A 125.13(18) . . ? C27A N3A H3A 117.4 . . ? C25A N3A H3A 117.4 . . ? O9A N4A O10A 120.31(18) . . ? O9A N4A C31A 119.82(17) . . ? O10A N4A C31A 119.88(17) . . ? O6A C24A O5A 127.9(2) . . ? O6A C24A C25A 116.99(18) . . ? O5A C24A C25A 115.07(19) . . ? N3A C25A C26A 111.37(18) . . ? N3A C25A C24A 110.04(17) . . ? C26A C25A C24A 111.49(17) . . ? N3A C25A H25A 107.9 . . ? C26A C25A H25A 107.9 . . ? C24A C25A H25A 107.9 . . ? O7A C26A C25A 108.06(17) . . ? O7A C26A H26C 110.1 . . ? C25A C26A H26C 110.1 . . ? O7A C26A H26D 110.1 . . ? C25A C26A H26D 110.1 . . ? H26C C26A H26D 108.4 . . ? O8A C27A N3A 120.63(19) . . ? O8A C27A C28A 123.31(18) . . ? N3A C27A C28A 116.02(18) . . ? C29A C28A C33A 116.69(19) . . ? C29A C28A C27A 119.93(18) . . ? C33A C28A C27A 123.38(18) . . ? C28A C29A C30A 121.67(19) . . ? C28A C29A H29A 119.2 . . ? C30A C29A H29A 119.2 . . ? C31A C30A C29A 120.14(18) . . ? C31A C30A H30A 119.9 . . ? C29A C30A H30A 119.9 . . ? C32A C31A C30A 119.67(19) . . ? C32A C31A N4A 119.86(18) . . ? C30A C31A N4A 120.47(18) . . ? C31A C32A C33A 119.78(19) . . ? C31A C32A H32A 120.1 . . ? C33A C32A H32A 120.1 . . ? C28A C33A C32A 122.04(18) . . ? C28A C33A H33A 119.0 . . ? C32A C33A H33A 119.0 . . ? H11W O1W H12W 108.4 . . ? H21W O2W H22W 108.9 . . ? H31W O3W H32W 108.8 . . ? H41W O4W H42W 108.6 . . ? H51W O5W H52W 108.1 . . ? H61W O6W H62W 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 C3 178.9(2) . . . . ? C22 O2 C2 C1 -2.0(3) . . . . ? C6 C1 C2 O2 178.5(2) . . . . ? C6 C1 C2 C3 -2.6(3) . . . . ? C23 O3 C3 C4 -5.8(3) . . . . ? C23 O3 C3 C2 174.1(2) . . . . ? O2 C2 C3 C4 -177.0(2) . . . . ? C1 C2 C3 C4 3.9(3) . . . . ? O2 C2 C3 O3 3.1(3) . . . . ? C1 C2 C3 O3 -176.0(2) . . . . ? O3 C3 C4 C5 178.38(19) . . . . ? C2 C3 C4 C5 -1.5(3) . . . . ? C3 C4 C5 C6 -2.1(3) . . . . ? C3 C4 C5 C7 -175.5(2) . . . . ? C2 C1 C6 C5 -1.1(3) . . . . ? C2 C1 C6 N1 179.8(2) . . . . ? C4 C5 C6 C1 3.4(3) . . . . ? C7 C5 C6 C1 178.05(19) . . . . ? C4 C5 C6 N1 -177.36(19) . . . . ? C7 C5 C6 N1 -2.7(2) . . . . ? C9 N1 C6 C1 15.1(4) . . . . ? C8 N1 C6 C1 170.9(2) . . . . ? C9 N1 C6 C5 -164.0(2) . . . . ? C8 N1 C6 C5 -8.2(2) . . . . ? C6 C5 C7 C21 135.99(18) . . . . ? C4 C5 C7 C21 -49.8(3) . . . . ? C6 C5 C7 C17 -109.17(19) . . . . ? C4 C5 C7 C17 65.1(3) . . . . ? C6 C5 C7 C8 11.2(2) . . . . ? C4 C5 C7 C8 -174.6(2) . . . . ? C9 N1 C8 C18 47.3(2) . . . . ? C6 N1 C8 C18 -111.95(17) . . . . ? C9 N1 C8 C7 173.49(17) . . . . ? C6 N1 C8 C7 14.3(2) . . . . ? C5 C7 C8 N1 -15.8(2) . . . . ? C21 C7 C8 N1 -139.14(17) . . . . ? C17 C7 C8 N1 104.51(18) . . . . ? C5 C7 C8 C18 100.3(2) . . . . ? C21 C7 C8 C18 -23.0(2) . . . . ? C17 C7 C8 C18 -139.35(18) . . . . ? C8 N1 C9 O4 -175.4(2) . . . . ? C6 N1 C9 O4 -21.7(3) . . . . ? C8 N1 C9 C10 5.8(3) . . . . ? C6 N1 C9 C10 159.5(2) . . . . ? O4 C9 C10 C11 145.6(2) . . . . ? N1 C9 C10 C11 -35.6(3) . . . . ? C12 O1 C11 C10 170.42(16) . . . . ? C12 O1 C11 C18 -69.2(2) . . . . ? C9 C10 C11 O1 130.60(18) . . . . ? C9 C10 C11 C18 7.3(3) . . . . ? C11 O1 C12 C13 87.7(2) . . . . ? O1 C12 C13 C14 -65.3(3) . . . . ? C12 C13 C14 C19 -2.9(3) . . . . ? C12 C13 C14 C15 177.04(19) . . . . ? C16 N2 C15 C14 73.3(2) . . . . ? C21 N2 C15 C14 -48.8(2) . . . . ? C13 C14 C15 N2 -124.1(2) . . . . ? C19 C14 C15 N2 55.8(2) . . . . ? C21 N2 C16 C17 -18.8(2) . . . . ? C15 N2 C16 C17 -141.49(16) . . . . ? N2 C16 C17 C7 38.2(2) . . . . ? C5 C7 C17 C16 -165.30(17) . . . . ? C21 C7 C17 C16 -44.8(2) . . . . ? C8 C7 C17 C16 78.50(19) . . . . ? N1 C8 C18 C19 153.52(17) . . . . ? C7 C8 C18 C19 37.3(2) . . . . ? N1 C8 C18 C11 -72.58(18) . . . . ? C7 C8 C18 C11 171.24(15) . . . . ? O1 C11 C18 C19 57.1(2) . . . . ? C10 C11 C18 C19 172.96(19) . . . . ? O1 C11 C18 C8 -71.7(2) . . . . ? C10 C11 C18 C8 44.1(2) . . . . ? C13 C14 C19 C18 57.2(3) . . . . ? C15 C14 C19 C18 -122.79(19) . . . . ? C13 C14 C19 C20 176.79(19) . . . . ? C15 C14 C19 C20 -3.2(2) . . . . ? C8 C18 C19 C14 61.9(2) . . . . ? C11 C18 C19 C14 -65.6(2) . . . . ? C8 C18 C19 C20 -57.7(2) . . . . ? C11 C18 C19 C20 174.79(17) . . . . ? C14 C19 C20 C21 -53.7(2) . . . . ? C18 C19 C20 C21 68.5(2) . . . . ? C16 N2 C21 C7 -8.8(2) . . . . ? C15 N2 C21 C7 113.63(17) . . . . ? C16 N2 C21 C20 -131.03(18) . . . . ? C15 N2 C21 C20 -8.6(2) . . . . ? C5 C7 C21 N2 151.62(16) . . . . ? C17 C7 C21 N2 31.78(19) . . . . ? C8 C7 C21 N2 -89.32(18) . . . . ? C5 C7 C21 C20 -88.0(2) . . . . ? C17 C7 C21 C20 152.19(17) . . . . ? C8 C7 C21 C20 31.1(2) . . . . ? C19 C20 C21 N2 61.0(2) . . . . ? C19 C20 C21 C7 -54.0(2) . . . . ? C6A C1A C2A O2A -178.8(2) . . . . ? C6A C1A C2A C3A 1.9(3) . . . . ? C22A O2A C2A C1A 6.4(4) . . . . ? C22A O2A C2A C3A -174.3(2) . . . . ? C23A O3A C3A C2A 174.40(18) . . . . ? C23A O3A C3A C4A -5.0(3) . . . . ? C1A C2A C3A O3A 176.5(2) . . . . ? O2A C2A C3A O3A -2.9(3) . . . . ? C1A C2A C3A C4A -4.1(3) . . . . ? O2A C2A C3A C4A 176.6(2) . . . . ? O3A C3A C4A C5A -177.9(2) . . . . ? C2A C3A C4A C5A 2.7(3) . . . . ? C3A C4A C5A C6A 0.7(3) . . . . ? C3A C4A C5A C7A -173.79(19) . . . . ? C9A N1A C6A C5A -160.52(19) . . . . ? C8A N1A C6A C5A -4.5(2) . . . . ? C9A N1A C6A C1A 20.1(3) . . . . ? C8A N1A C6A C1A 176.2(2) . . . . ? C4A C5A C6A N1A 177.68(19) . . . . ? C7A C5A C6A N1A -7.0(2) . . . . ? C4A C5A C6A C1A -3.0(3) . . . . ? C7A C5A C6A C1A 172.36(19) . . . . ? C2A C1A C6A N1A -179.2(2) . . . . ? C2A C1A C6A C5A 1.6(3) . . . . ? C4A C5A C7A C8A -170.1(2) . . . . ? C6A C5A C7A C8A 15.2(2) . . . . ? C4A C5A C7A C17A 71.9(3) . . . . ? C6A C5A C7A C17A -102.8(2) . . . . ? C4A C5A C7A C21A -46.4(3) . . . . ? C6A C5A C7A C21A 138.94(19) . . . . ? C17A C7A C8A C18A -137.68(17) . . . . ? C5A C7A C8A C18A 102.92(18) . . . . ? C21A C7A C8A C18A -24.2(2) . . . . ? C17A C7A C8A N1A 103.37(17) . . . . ? C5A C7A C8A N1A -16.03(18) . . . . ? C21A C7A C8A N1A -143.19(16) . . . . ? C9A N1A C8A C7A 171.29(18) . . . . ? C6A N1A C8A C7A 14.1(2) . . . . ? C9A N1A C8A C18A 45.2(2) . . . . ? C6A N1A C8A C18A -112.04(18) . . . . ? C6A N1A C9A O4A -17.5(3) . . . . ? C8A N1A C9A O4A -171.56(19) . . . . ? C6A N1A C9A C10A 165.19(19) . . . . ? C8A N1A C9A C10A 11.1(3) . . . . ? O4A C9A C10A C11A 139.2(2) . . . . ? N1A C9A C10A C11A -43.5(3) . . . . ? C12A O1A C11A C18A -65.7(2) . . . . ? C12A O1A C11A C10A 173.53(16) . . . . ? C9A C10A C11A O1A 137.83(18) . . . . ? C9A C10A C11A C18A 14.9(3) . . . . ? C11A O1A C12A C13A 92.9(2) . . . . ? O1A C12A C13A C14A -66.6(3) . . . . ? C12A C13A C14A C15A 177.64(19) . . . . ? C12A C13A C14A C19A -2.5(3) . . . . ? C13A C14A C15A N2A -127.4(2) . . . . ? C19A C14A C15A N2A 52.8(2) . . . . ? C16A N2A C15A C14A 76.1(2) . . . . ? C21A N2A C15A C14A -45.7(2) . . . . ? C15A N2A C16A C17A -143.01(17) . . . . ? C21A N2A C16A C17A -16.59(19) . . . . ? C8A C7A C17A C16A 81.07(18) . . . . ? C5A C7A C17A C16A -167.39(15) . . . . ? C21A C7A C17A C16A -39.69(18) . . . . ? N2A C16A C17A C7A 36.08(19) . . . . ? O1A C11A C18A C8A -78.1(2) . . . . ? C10A C11A C18A C8A 41.0(2) . . . . ? O1A C11A C18A C19A 50.9(2) . . . . ? C10A C11A C18A C19A 170.03(17) . . . . ? C7A C8A C18A C11A 170.27(16) . . . . ? N1A C8A C18A C11A -71.69(18) . . . . ? C7A C8A C18A C19A 38.4(2) . . . . ? N1A C8A C18A C19A 156.44(15) . . . . ? C13A C14A C19A C20A 178.5(2) . . . . ? C15A C14A C19A C20A -1.6(3) . . . . ? C13A C14A C19A C18A 60.4(3) . . . . ? C15A C14A C19A C18A -119.8(2) . . . . ? C11A C18A C19A C20A 174.74(18) . . . . ? C8A C18A C19A C20A -59.8(2) . . . . ? C11A C18A C19A C14A -65.1(2) . . . . ? C8A C18A C19A C14A 60.3(2) . . . . ? C14A C19A C20A C21A -56.5(2) . . . . ? C18A C19A C20A C21A 68.9(2) . . . . ? C19A C20A C21A C7A -59.2(2) . . . . ? C19A C20A C21A N2A 62.1(2) . . . . ? C8A C7A C21A C20A 34.1(2) . . . . ? C17A C7A C21A C20A 153.06(16) . . . . ? C5A C7A C21A C20A -82.9(2) . . . . ? C8A C7A C21A N2A -89.06(19) . . . . ? C17A C7A C21A N2A 29.93(18) . . . . ? C5A C7A C21A N2A 153.97(16) . . . . ? C15A N2A C21A C20A -8.1(2) . . . . ? C16A N2A C21A C20A -134.68(17) . . . . ? C15A N2A C21A C7A 118.24(17) . . . . ? C16A N2A C21A C7A -8.36(19) . . . . ? C27 N3 C25 C26 -90.3(2) . . . . ? C27 N3 C25 C24 146.13(19) . . . . ? O6 C24 C25 N3 -158.45(19) . . . . ? O5 C24 C25 N3 23.3(3) . . . . ? O6 C24 C25 C26 79.3(2) . . . . ? O5 C24 C25 C26 -99.0(2) . . . . ? N3 C25 C26 O7 -59.3(2) . . . . ? C24 C25 C26 O7 63.1(2) . . . . ? C25 N3 C27 O8 0.2(3) . . . . ? C25 N3 C27 C28 -177.35(19) . . . . ? O8 C27 C28 C29 -10.4(3) . . . . ? N3 C27 C28 C29 167.29(19) . . . . ? O8 C27 C28 C33 169.0(2) . . . . ? N3 C27 C28 C33 -13.3(3) . . . . ? C33 C28 C29 C30 1.7(3) . . . . ? C27 C28 C29 C30 -178.9(2) . . . . ? C28 C29 C30 C31 0.0(3) . . . . ? C29 C30 C31 C32 -1.8(3) . . . . ? C29 C30 C31 N4 178.4(2) . . . . ? O9 N4 C31 C30 -10.3(3) . . . . ? O10 N4 C31 C30 170.7(2) . . . . ? O9 N4 C31 C32 169.9(2) . . . . ? O10 N4 C31 C32 -9.2(3) . . . . ? C30 C31 C32 C33 1.9(3) . . . . ? N4 C31 C32 C33 -178.3(2) . . . . ? C31 C32 C33 C28 -0.2(3) . . . . ? C29 C28 C33 C32 -1.5(3) . . . . ? C27 C28 C33 C32 179.1(2) . . . . ? C27A N3A C25A C26A -98.3(2) . . . . ? C27A N3A C25A C24A 137.5(2) . . . . ? O6A C24A C25A N3A 22.5(2) . . . . ? O5A C24A C25A N3A -159.16(16) . . . . ? O6A C24A C25A C26A -101.6(2) . . . . ? O5A C24A C25A C26A 76.7(2) . . . . ? N3A C25A C26A O7A -55.8(2) . . . . ? C24A C25A C26A O7A 67.5(2) . . . . ? C25A N3A C27A O8A -0.8(3) . . . . ? C25A N3A C27A C28A -178.59(18) . . . . ? O8A C27A C28A C29A -31.0(3) . . . . ? N3A C27A C28A C29A 146.7(2) . . . . ? O8A C27A C28A C33A 149.7(2) . . . . ? N3A C27A C28A C33A -32.6(3) . . . . ? C33A C28A C29A C30A 1.6(3) . . . . ? C27A C28A C29A C30A -177.7(2) . . . . ? C28A C29A C30A C31A -0.7(4) . . . . ? C29A C30A C31A C32A -0.3(4) . . . . ? C29A C30A C31A N4A 178.8(2) . . . . ? O9A N4A C31A C32A -176.0(2) . . . . ? O10A N4A C31A C32A 3.9(3) . . . . ? O9A N4A C31A C30A 4.8(3) . . . . ? O10A N4A C31A C30A -175.3(2) . . . . ? C30A C31A C32A C33A 0.4(4) . . . . ? N4A C31A C32A C33A -178.7(2) . . . . ? C29A C28A C33A C32A -1.5(3) . . . . ? C27A C28A C33A C32A 177.8(2) . . . . ? C31A C32A C33A C28A 0.5(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 H2 O5 0.93 2.21 3.005(2) 143.4 . N2 H2 O5W 0.93 2.43 3.045(2) 123.7 . N2A H2A O2W 0.93 2.03 2.865(2) 148.2 . N2A H2A O7A 0.93 2.42 3.044(2) 124.4 . O7 H7 O4W 0.90 1.88 2.768(2) 168.7 1_545 N3 H3 O5W 0.88 2.52 3.346(2) 156.2 . O7A H7A O1W 0.82 2.01 2.796(2) 160.5 1_565 N3A H3A O2W 0.88 2.53 3.325(2) 151.2 . O1W H11W O6 0.86 2.02 2.882(2) 176.2 1_455 O1W H12W O6A 0.86 1.94 2.783(2) 167.6 . O2W H21W O6 0.86 2.06 2.883(2) 161.2 1_455 O2W H22W O6A 0.86 1.89 2.746(2) 171.5 . O3W H31W O1 0.86 1.99 2.853(2) 176.0 . O3W H32W O4 0.86 1.89 2.702(2) 157.4 2_647 O4W H41W O5 0.86 1.89 2.717(2) 161.5 . O4W H42W O5A 0.86 1.99 2.839(2) 167.9 . O5W H51W O8A 0.86 2.13 2.979(2) 171.2 1_545 O5W H52W O5A 0.86 1.87 2.715(2) 167.5 . O6W H61W O4A 0.86 2.07 2.928(2) 173.8 . O6W H62W O1A 0.86 2.08 2.923(3) 167.4 2_546 _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 31.00 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.325 _refine_diff_density_min -0.277 _refine_diff_density_rms 0.052 #==== END data_3 _database_code_depnum_ccdc_archive 'CCDC 758144' #TrackingRef 'bialonska1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; brucinium N-(4-nitrobenzoyl)-L-serinate 1.66-hydrate methanol 1.66-solvate ; _chemical_name_common ;brucinium N-(4-nitrobenzoyl)-L-serinate 1.66-hydrate methanol 1.66-solvate ; _chemical_melting_point ? _chemical_formula_moiety 'C23 H27 N2 O4, C10 H9 N2 O6, 1.66(C H4 O) 1.66(H2 O)' _chemical_formula_sum 'C34.67 H46 N4 O13.33' _chemical_formula_weight 732.09 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 17.561(4) _cell_length_b 12.479(3) _cell_length_c 23.694(4) _cell_angle_alpha 90.00 _cell_angle_beta 101.91(3) _cell_angle_gamma 90.00 _cell_volume 5080.6(19) _cell_formula_units_Z 6 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 46250 _cell_measurement_theta_min 3.09 _cell_measurement_theta_max 36.80 _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.436 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2332 _exptl_absorpt_coefficient_mu 0.111 _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 86736 _diffrn_reflns_av_R_equivalents 0.0603 _diffrn_reflns_av_sigmaI/netI 0.0588 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -38 _diffrn_reflns_limit_l_max 38 _diffrn_reflns_theta_min 3.10 _diffrn_reflns_theta_max 35.00 _reflns_number_total 22768 _reflns_number_gt 18347 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET) (compiled May 8 2007,13:10:02) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET) (compiled May 8 2007,13:10:02) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET) (compiled May 8 2007,13:10:02) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0727P)^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 22768 _refine_ls_number_parameters 1459 _refine_ls_number_restraints 85 _refine_ls_R_factor_all 0.0790 _refine_ls_R_factor_gt 0.0587 _refine_ls_wR_factor_ref 0.1344 _refine_ls_wR_factor_gt 0.1267 _refine_ls_goodness_of_fit_ref 1.061 _refine_ls_restrained_S_all 1.061 _refine_ls_shift/su_max 0.005 _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 0.60362(9) 0.44680(13) 0.60601(7) 0.0162(3) Uani 1 1 d . . . O2 O 0.34444(9) 1.03353(13) 0.58306(7) 0.0158(3) Uani 1 1 d . . . O3 O 0.47197(9) 1.14035(12) 0.58471(7) 0.0160(3) Uani 1 1 d . . . O4 O 0.37560(9) 0.64045(14) 0.59250(8) 0.0219(3) Uani 1 1 d . . . N1 N 0.49992(10) 0.70170(14) 0.61763(8) 0.0129(3) Uani 1 1 d . . . N2 N 0.76256(10) 0.77350(15) 0.63577(8) 0.0146(3) Uani 1 1 d . . . H2 H 0.7992 0.8284 0.6402 0.018 Uiso 1 1 calc R . . C1 C 0.41256(12) 0.86395(17) 0.60052(9) 0.0129(3) Uani 1 1 d . . . H1 H 0.3659 0.8246 0.5990 0.016 Uiso 1 1 calc R . . C2 C 0.41127(11) 0.97403(17) 0.59255(9) 0.0124(3) Uani 1 1 d . . . C3 C 0.48105(12) 1.03247(16) 0.59431(8) 0.0124(3) Uani 1 1 d . . . C4 C 0.55226(12) 0.97944(16) 0.60568(9) 0.0130(3) Uani 1 1 d . . . H4 H 0.5994 1.0181 0.6078 0.016 Uiso 1 1 calc R . . C5 C 0.55349(12) 0.86878(16) 0.61392(9) 0.0127(3) Uani 1 1 d . . . C6 C 0.48478(11) 0.81285(16) 0.61083(9) 0.0127(3) Uani 1 1 d . . . C7 C 0.62254(12) 0.79402(17) 0.62963(9) 0.0129(3) Uani 1 1 d . . . C8 C 0.58325(11) 0.68141(16) 0.61870(8) 0.0113(3) Uani 1 1 d . . . H8 H 0.6051 0.6322 0.6514 0.014 Uiso 1 1 calc R . . C9 C 0.44550(12) 0.62409(17) 0.59834(9) 0.0144(4) Uani 1 1 d . . . C10 C 0.47642(12) 0.51572(17) 0.58473(10) 0.0169(4) Uani 1 1 d . . . H10A H 0.4366 0.4816 0.5544 0.020 Uiso 1 1 calc R . . H10B H 0.4820 0.4706 0.6197 0.020 Uiso 1 1 calc R . . C11 C 0.55476(12) 0.51328(17) 0.56453(9) 0.0143(4) Uani 1 1 d . . . H11 H 0.5470 0.4790 0.5256 0.017 Uiso 1 1 calc R . . C12 C 0.67524(13) 0.41591(18) 0.59102(11) 0.0192(4) Uani 1 1 d . . . H12A H 0.6667 0.4059 0.5487 0.023 Uiso 1 1 calc R . . H12B H 0.6924 0.3464 0.6095 0.023 Uiso 1 1 calc R . . C13 C 0.73825(13) 0.49774(18) 0.60945(10) 0.0174(4) Uani 1 1 d . . . H13 H 0.7834 0.4770 0.6367 0.021 Uiso 1 1 calc R . . C14 C 0.73411(12) 0.59813(17) 0.58950(9) 0.0153(4) Uani 1 1 d . . . C15 C 0.79730(12) 0.67730(18) 0.61213(10) 0.0174(4) Uani 1 1 d . . . H15A H 0.8232 0.6997 0.5807 0.021 Uiso 1 1 calc R . . H15B H 0.8368 0.6437 0.6429 0.021 Uiso 1 1 calc R . . C16 C 0.74390(13) 0.75183(19) 0.69419(10) 0.0180(4) Uani 1 1 d . . . H16A H 0.7846 0.7823 0.7252 0.022 Uiso 1 1 calc R . . H16B H 0.7403 0.6738 0.7007 0.022 Uiso 1 1 calc R . . C17 C 0.66583(12) 0.80593(18) 0.69296(9) 0.0153(4) Uani 1 1 d . . . H17A H 0.6729 0.8824 0.7040 0.018 Uiso 1 1 calc R . . H17B H 0.6372 0.7697 0.7194 0.018 Uiso 1 1 calc R . . C18 C 0.58660(11) 0.62735(16) 0.56147(9) 0.0126(3) Uani 1 1 d . . . H18 H 0.5481 0.6658 0.5312 0.015 Uiso 1 1 calc R . . C19 C 0.66614(12) 0.64096(17) 0.54495(9) 0.0147(4) Uani 1 1 d . . . H19 H 0.6651 0.6042 0.5073 0.018 Uiso 1 1 calc R . . C20 C 0.67670(12) 0.76204(17) 0.53730(9) 0.0154(4) Uani 1 1 d . . . H20A H 0.7226 0.7754 0.5201 0.018 Uiso 1 1 calc R . . H20B H 0.6302 0.7922 0.5112 0.018 Uiso 1 1 calc R . . C21 C 0.68795(11) 0.81477(17) 0.59619(9) 0.0138(4) Uani 1 1 d . . . H21 H 0.6930 0.8939 0.5912 0.017 Uiso 1 1 calc R . . C22 C 0.27309(12) 0.97422(19) 0.57142(11) 0.0193(4) Uani 1 1 d . . . H22A H 0.2290 1.0240 0.5656 0.029 Uiso 1 1 calc R . . H22B H 0.2709 0.9271 0.6042 0.029 Uiso 1 1 calc R . . H22C H 0.2706 0.9309 0.5366 0.029 Uiso 1 1 calc R . . C23 C 0.54203(13) 1.20161(18) 0.58910(11) 0.0201(4) Uani 1 1 d . . . H23A H 0.5288 1.2772 0.5814 0.030 Uiso 1 1 calc R . . H23B H 0.5712 1.1752 0.5609 0.030 Uiso 1 1 calc R . . H23C H 0.5739 1.1943 0.6281 0.030 Uiso 1 1 calc R . . O1A O 0.63463(9) 0.44800(14) 0.27607(7) 0.0208(3) Uani 1 1 d . . . O2A O 0.34520(9) 1.02535(13) 0.24191(8) 0.0202(3) Uani 1 1 d . . . O3A O 0.46838(10) 1.13705(13) 0.24286(8) 0.0209(3) Uani 1 1 d . . . O4A O 0.39245(9) 0.62485(14) 0.24244(7) 0.0181(3) Uani 1 1 d . . . N1A N 0.51064(10) 0.70051(14) 0.28000(8) 0.0127(3) Uani 1 1 d . . . N2A N 0.77043(10) 0.79146(16) 0.32008(8) 0.0174(3) Uani 1 1 d . . . H2A H 0.8048 0.8489 0.3279 0.021 Uiso 1 1 calc R . . C1A C 0.41736(11) 0.85735(17) 0.25983(9) 0.0135(4) Uani 1 1 d . . . H1A H 0.3717 0.8153 0.2575 0.016 Uiso 1 1 calc R . . C2A C 0.41325(12) 0.96794(18) 0.25189(9) 0.0153(4) Uani 1 1 d . . . C3A C 0.48117(12) 1.03030(17) 0.25361(9) 0.0152(4) Uani 1 1 d . . . C4A C 0.55368(12) 0.98198(17) 0.26733(9) 0.0156(4) Uani 1 1 d . . . H4A H 0.5997 1.0235 0.2701 0.019 Uiso 1 1 calc R . . C5A C 0.55838(12) 0.87153(17) 0.27710(9) 0.0143(4) Uani 1 1 d . . . C6A C 0.49122(11) 0.81071(16) 0.27133(8) 0.0122(3) Uani 1 1 d . . . C7A C 0.62884(11) 0.80327(17) 0.29962(9) 0.0140(4) Uani 1 1 d . . . C8A C 0.59637(11) 0.68752(17) 0.28820(9) 0.0128(3) Uani 1 1 d . . . H8A H 0.6159 0.6418 0.3228 0.015 Uiso 1 1 calc R . . C9A C 0.46322(12) 0.61599(17) 0.25806(8) 0.0132(3) Uani 1 1 d . . . C10A C 0.50559(13) 0.51083(17) 0.25574(9) 0.0157(4) Uani 1 1 d . . . H10C H 0.4705 0.4620 0.2295 0.019 Uiso 1 1 calc R . . H10D H 0.5150 0.4784 0.2947 0.019 Uiso 1 1 calc R . . C11A C 0.58419(12) 0.51515(17) 0.23588(9) 0.0158(4) Uani 1 1 d . . . H11A H 0.5774 0.4833 0.1964 0.019 Uiso 1 1 calc R . . C12A C 0.70969(14) 0.4285(2) 0.26261(12) 0.0263(5) Uani 1 1 d . . . H12C H 0.7047 0.4281 0.2202 0.032 Uiso 1 1 calc R . . H12D H 0.7288 0.3571 0.2775 0.032 Uiso 1 1 calc R . . C13A C 0.76720(14) 0.5120(2) 0.28847(11) 0.0232(5) Uani 1 1 d . . . H13A H 0.8109 0.4917 0.3172 0.028 Uiso 1 1 calc R . . C14A C 0.75885(12) 0.6140(2) 0.27231(10) 0.0198(4) Uani 1 1 d . . . C15A C 0.81392(12) 0.6987(2) 0.30127(11) 0.0213(4) Uani 1 1 d . . . H15C H 0.8460 0.7245 0.2742 0.026 Uiso 1 1 calc R . . H15D H 0.8493 0.6675 0.3353 0.026 Uiso 1 1 calc R . . C16A C 0.74069(12) 0.7680(2) 0.37454(10) 0.0185(4) Uani 1 1 d . . . H16C H 0.7759 0.7985 0.4088 0.022 Uiso 1 1 calc R . . H16D H 0.7362 0.6898 0.3801 0.022 Uiso 1 1 calc R . . C17A C 0.66123(12) 0.82132(18) 0.36468(9) 0.0160(4) Uani 1 1 d . . . H17C H 0.6660 0.8987 0.3740 0.019 Uiso 1 1 calc R . . H17D H 0.6276 0.7872 0.3883 0.019 Uiso 1 1 calc R . . C18A C 0.61143(12) 0.63134(18) 0.23408(9) 0.0161(4) Uani 1 1 d . . . H18A H 0.5751 0.6654 0.2009 0.019 Uiso 1 1 calc R . . C19A C 0.69351(12) 0.65208(19) 0.22381(9) 0.0163(4) Uani 1 1 d . . . H19A H 0.6989 0.6159 0.1872 0.020 Uiso 1 1 calc R . . C20A C 0.70115(13) 0.77334(19) 0.21651(10) 0.0182(4) Uani 1 1 d . . . H20C H 0.7503 0.7898 0.2041 0.022 Uiso 1 1 calc R . . H20D H 0.6574 0.8001 0.1866 0.022 Uiso 1 1 calc R . . C21A C 0.70052(12) 0.82782(19) 0.27367(9) 0.0166(4) Uani 1 1 d . . . H21A H 0.7039 0.9071 0.2684 0.020 Uiso 1 1 calc R . . C22A C 0.27564(13) 0.9664(2) 0.24158(11) 0.0205(4) Uani 1 1 d . . . H22D H 0.2310 1.0154 0.2345 0.031 Uiso 1 1 calc R . . H22E H 0.2791 0.9311 0.2790 0.031 Uiso 1 1 calc R . . H22F H 0.2689 0.9122 0.2110 0.031 Uiso 1 1 calc R . . C23A C 0.53606(15) 1.2017(2) 0.24449(11) 0.0240(5) Uani 1 1 d . . . H23D H 0.5203 1.2762 0.2358 0.036 Uiso 1 1 calc R . . H23E H 0.5646 1.1754 0.2158 0.036 Uiso 1 1 calc R . . H23F H 0.5696 1.1977 0.2830 0.036 Uiso 1 1 calc R . . O1B O 0.37904(10) 0.48071(14) 0.06246(7) 0.0208(3) Uani 1 1 d . . . O2B O 0.65633(10) 1.06741(15) 0.09945(8) 0.0250(4) Uani 1 1 d . . . O3B O 0.53054(10) 1.17612(14) 0.09184(8) 0.0227(3) Uani 1 1 d . . . O4B O 0.61619(9) 0.66820(15) 0.08739(8) 0.0226(3) Uani 1 1 d . . . N1B N 0.49706(10) 0.74068(16) 0.04964(8) 0.0157(3) Uani 1 1 d . . . N2B N 0.23605(10) 0.81792(15) 0.00738(8) 0.0145(3) Uani 1 1 d . . . H2B H 0.1997 0.8727 -0.0017 0.017 Uiso 1 1 calc R . . C1B C 0.58717(12) 0.8993(2) 0.07493(10) 0.0186(4) Uani 1 1 d . . . H1B H 0.6337 0.8588 0.0784 0.022 Uiso 1 1 calc R . . C2B C 0.58909(12) 1.0088(2) 0.08497(10) 0.0188(4) Uani 1 1 d . . . C3B C 0.52014(13) 1.06883(19) 0.08015(10) 0.0174(4) Uani 1 1 d . . . C4B C 0.44805(12) 1.02000(19) 0.06302(9) 0.0160(4) Uani 1 1 d . . . H4B H 0.4014 1.0605 0.0587 0.019 Uiso 1 1 calc R . . C5B C 0.44569(12) 0.90981(18) 0.05231(9) 0.0145(4) Uani 1 1 d . . . C6B C 0.51419(12) 0.85098(19) 0.05946(9) 0.0161(4) Uani 1 1 d . . . C7B C 0.37656(12) 0.83900(18) 0.02896(9) 0.0140(4) Uani 1 1 d . . . C8B C 0.41135(12) 0.72451(17) 0.04168(9) 0.0136(4) Uani 1 1 d . . . H8B H 0.3925 0.6766 0.0079 0.016 Uiso 1 1 calc R . . C9B C 0.54543(13) 0.65798(19) 0.07165(9) 0.0175(4) Uani 1 1 d . . . C10B C 0.50466(13) 0.55189(19) 0.07436(10) 0.0184(4) Uani 1 1 d . . . H10E H 0.5415 0.5024 0.0988 0.022 Uiso 1 1 calc R . . H10F H 0.4923 0.5211 0.0350 0.022 Uiso 1 1 calc R . . C11B C 0.42887(13) 0.55533(18) 0.09789(9) 0.0172(4) Uani 1 1 d . . . H11B H 0.4401 0.5287 0.1386 0.021 Uiso 1 1 calc R . . C12B C 0.30482(14) 0.4613(2) 0.07777(11) 0.0232(5) Uani 1 1 d . . . H12E H 0.3099 0.4698 0.1199 0.028 Uiso 1 1 calc R . . H12F H 0.2877 0.3871 0.0673 0.028 Uiso 1 1 calc R . . C13B C 0.24588(13) 0.5389(2) 0.04662(10) 0.0199(4) Uani 1 1 d . . . H13B H 0.2039 0.5134 0.0178 0.024 Uiso 1 1 calc R . . C14B C 0.25159(12) 0.64356(19) 0.05882(9) 0.0174(4) Uani 1 1 d . . . C15B C 0.19516(12) 0.72346(19) 0.02714(10) 0.0178(4) Uani 1 1 d . . . H15E H 0.1608 0.7488 0.0527 0.021 Uiso 1 1 calc R . . H15F H 0.1621 0.6885 -0.0068 0.021 Uiso 1 1 calc R . . C16B C 0.26732(12) 0.79499(19) -0.04583(9) 0.0170(4) Uani 1 1 d . . . H16E H 0.2314 0.8221 -0.0807 0.020 Uiso 1 1 calc R . . H16F H 0.2747 0.7170 -0.0503 0.020 Uiso 1 1 calc R . . C17B C 0.34489(12) 0.85366(18) -0.03637(9) 0.0155(4) Uani 1 1 d . . . H17E H 0.3376 0.9304 -0.0466 0.019 Uiso 1 1 calc R . . H17F H 0.3801 0.8210 -0.0592 0.019 Uiso 1 1 calc R . . C18B C 0.39790(12) 0.67108(18) 0.09691(9) 0.0146(4) Uani 1 1 d . . . H18B H 0.4331 0.7090 0.1294 0.017 Uiso 1 1 calc R . . C19B C 0.31487(12) 0.68814(18) 0.10684(9) 0.0157(4) Uani 1 1 d . . . H19B H 0.3104 0.6535 0.1441 0.019 Uiso 1 1 calc R . . C20B C 0.30332(12) 0.80878(18) 0.11165(9) 0.0162(4) Uani 1 1 d . . . H20E H 0.2533 0.8232 0.1233 0.019 Uiso 1 1 calc R . . H20F H 0.3458 0.8392 0.1414 0.019 Uiso 1 1 calc R . . C21B C 0.30320(11) 0.86078(18) 0.05353(9) 0.0138(4) Uani 1 1 d . . . H21B H 0.2968 0.9400 0.0571 0.017 Uiso 1 1 calc R . . C22B C 0.72860(14) 1.0089(2) 0.10797(14) 0.0320(6) Uani 1 1 d . . . H22G H 0.7723 1.0589 0.1183 0.048 Uiso 1 1 calc R . . H22H H 0.7322 0.9713 0.0723 0.048 Uiso 1 1 calc R . . H22I H 0.7304 0.9566 0.1391 0.048 Uiso 1 1 calc R . . C23B C 0.46242(15) 1.2391(2) 0.08983(13) 0.0271(5) Uani 1 1 d . . . H23G H 0.4773 1.3138 0.0989 0.041 Uiso 1 1 calc R . . H23H H 0.4336 1.2117 0.1181 0.041 Uiso 1 1 calc R . . H23I H 0.4294 1.2351 0.0511 0.041 Uiso 1 1 calc R . . O5 O 0.85737(10) 0.93065(15) 0.62609(8) 0.0231(3) Uani 1 1 d . . . O6 O 0.93211(13) 0.87793(18) 0.70941(12) 0.0457(6) Uani 1 1 d . . . O7 O 1.04620(10) 1.02111(14) 0.62038(8) 0.0218(3) Uani 1 1 d . . . H7 H 1.0632 1.0532 0.5857 0.033 Uiso 1 1 d . . . O8 O 0.99385(12) 1.24507(14) 0.73255(8) 0.0254(4) Uani 1 1 d . . . O9 O 1.27078(11) 1.27261(17) 0.98400(8) 0.0297(4) Uani 1 1 d . . . O10 O 1.26807(11) 1.09993(17) 0.99246(8) 0.0294(4) Uani 1 1 d . . . N3 N 1.00475(11) 1.06586(16) 0.72923(8) 0.0178(4) Uani 1 1 d . . . H3 H 1.0279 1.0078 0.7455 0.021 Uiso 1 1 calc R . . N4 N 1.24675(12) 1.18434(19) 0.96709(9) 0.0224(4) Uani 1 1 d . . . C24 C 0.91057(13) 0.94461(19) 0.67034(11) 0.0215(4) Uani 1 1 d . . . C25 C 0.94766(13) 1.05664(18) 0.67551(9) 0.0173(4) Uani 1 1 d . . . H25 H 0.9052 1.1090 0.6776 0.021 Uiso 1 1 calc R . . C26 C 0.98051(12) 1.08686(19) 0.62324(10) 0.0175(4) Uani 1 1 d . . . H26A H 0.9400 1.0774 0.5877 0.021 Uiso 1 1 calc R . . H26B H 0.9963 1.1631 0.6259 0.021 Uiso 1 1 calc R . . C27 C 1.02266(12) 1.16109(18) 0.75424(9) 0.0155(4) Uani 1 1 d . . . C28 C 1.08183(12) 1.16293(18) 0.81027(9) 0.0159(4) Uani 1 1 d . . . C29 C 1.09803(13) 1.26170(19) 0.83779(10) 0.0182(4) Uani 1 1 d . . . H29 H 1.0716 1.3241 0.8211 0.022 Uiso 1 1 calc R . . C30 C 1.15208(13) 1.26980(19) 0.88908(10) 0.0189(4) Uani 1 1 d . . . H30 H 1.1633 1.3369 0.9079 0.023 Uiso 1 1 calc R . . C31 C 1.18930(13) 1.1775(2) 0.91222(9) 0.0178(4) Uani 1 1 d . . . C32 C 1.17494(15) 1.07863(19) 0.88648(10) 0.0226(5) Uani 1 1 d . . . H32 H 1.2015 1.0167 0.9037 0.027 Uiso 1 1 calc R . . C33 C 1.12095(15) 1.07145(19) 0.83495(11) 0.0224(5) Uani 1 1 d . . . H33 H 1.1105 1.0040 0.8163 0.027 Uiso 1 1 calc R . . O5A O 0.89387(10) 0.91368(16) 0.34733(8) 0.0257(4) Uani 1 1 d . . . O6A O 0.87019(10) 0.98305(17) 0.25887(8) 0.0264(4) Uani 1 1 d . . . O7A O 1.10090(10) 1.05921(17) 0.26660(9) 0.0284(4) Uani 1 1 d . . . H7A H 1.1048 1.1230 0.2510 0.043 Uiso 1 1 d . . . O8A O 1.07627(10) 1.00395(14) 0.43201(8) 0.0214(3) Uani 1 1 d . . . O9A O 1.23576(11) 0.51365(16) 0.54629(8) 0.0287(4) Uani 1 1 d . . . O10A O 1.30745(11) 0.52119(16) 0.48180(8) 0.0288(4) Uani 1 1 d . . . N3A N 1.05075(10) 0.91087(15) 0.34790(8) 0.0164(3) Uani 1 1 d . . . H3A H 1.0602 0.8512 0.3308 0.020 Uiso 1 1 calc R . . N4A N 1.25589(12) 0.55552(16) 0.50500(9) 0.0203(4) Uani 1 1 d . . . C24A C 0.91480(13) 0.95931(19) 0.30488(10) 0.0194(4) Uani 1 1 d . . . C25A C 1.00173(12) 0.99050(18) 0.31340(10) 0.0166(4) Uani 1 1 d . . . H25A H 1.0089 1.0594 0.3354 0.020 Uiso 1 1 calc R . . C26A C 1.02636(13) 1.0096(2) 0.25642(10) 0.0194(4) Uani 1 1 d . . . H26C H 1.0284 0.9405 0.2362 0.023 Uiso 1 1 calc R . . H26D H 0.9878 1.0563 0.2315 0.023 Uiso 1 1 calc R . . C27A C 1.08252(12) 0.92219(18) 0.40401(9) 0.0151(4) Uani 1 1 d . . . C28A C 1.12979(12) 0.82782(18) 0.43126(9) 0.0156(4) Uani 1 1 d . . . C29A C 1.13310(13) 0.80277(19) 0.48911(10) 0.0186(4) Uani 1 1 d . . . H29A H 1.1068 0.8469 0.5116 0.022 Uiso 1 1 calc R . . C30A C 1.17439(13) 0.71408(19) 0.51404(10) 0.0193(4) Uani 1 1 d . . . H30A H 1.1757 0.6960 0.5532 0.023 Uiso 1 1 calc R . . C31A C 1.21371(12) 0.65219(17) 0.48053(9) 0.0160(4) Uani 1 1 d . . . C32A C 1.21414(13) 0.67670(18) 0.42367(10) 0.0167(4) Uani 1 1 d . . . H32A H 1.2434 0.6351 0.4022 0.020 Uiso 1 1 calc R . . C33A C 1.17053(12) 0.76393(17) 0.39885(9) 0.0152(4) Uani 1 1 d . . . H33A H 1.1683 0.7805 0.3594 0.018 Uiso 1 1 calc R . . O5B O 0.10776(10) 0.93366(16) -0.01718(7) 0.0230(3) Uani 1 1 d . . . O6B O 0.14639(12) 0.9630(2) 0.07711(9) 0.0461(6) Uani 1 1 d . . . O7B O -0.08260(11) 1.06088(19) 0.08119(8) 0.0323(4) Uani 1 1 d . . . H7B H -0.0656 1.1210 0.0904 0.048 Uiso 1 1 d . . . O8B O 0.01128(11) 1.20963(16) -0.04750(8) 0.0266(4) Uani 1 1 d . . . O9B O -0.26294(10) 1.21538(15) -0.29946(8) 0.0220(3) Uani 1 1 d . . . O10B O -0.25761(11) 1.04234(15) -0.30458(8) 0.0256(4) Uani 1 1 d . . . N3B N -0.02653(11) 1.04425(16) -0.02501(8) 0.0175(3) Uani 1 1 d . . . H3B H -0.0582 0.9900 -0.0359 0.021 Uiso 1 1 calc R . . N4B N -0.23940(11) 1.12758(17) -0.27968(8) 0.0181(3) Uani 1 1 d . . . C24B C 0.09916(13) 0.9737(2) 0.03040(11) 0.0217(4) Uani 1 1 d . . . C25B C 0.02568(13) 1.04075(19) 0.03106(10) 0.0186(4) Uani 1 1 d . . . H25B H 0.0428 1.1158 0.0417 0.022 Uiso 1 1 calc R . . C26B C -0.01589(14) 0.9986(2) 0.07754(10) 0.0229(5) Uani 1 1 d . . . H26E H -0.0319 0.9234 0.0686 0.028 Uiso 1 1 calc R . . H26F H 0.0208 0.9995 0.1154 0.028 Uiso 1 1 calc R . . C27B C -0.02774(13) 1.12759(19) -0.06048(9) 0.0173(4) Uani 1 1 d . . . C28B C -0.08221(12) 1.12150(19) -0.11828(9) 0.0166(4) Uani 1 1 d . . . C29B C -0.09980(14) 1.21783(19) -0.14829(10) 0.0191(4) Uani 1 1 d . . . H29B H -0.0758 1.2824 -0.1324 0.023 Uiso 1 1 calc R . . C30B C -0.15171(13) 1.22038(19) -0.20079(10) 0.0188(4) Uani 1 1 d . . . H30B H -0.1641 1.2860 -0.2209 0.023 Uiso 1 1 calc R . . C31B C -0.18518(12) 1.12504(19) -0.22340(9) 0.0169(4) Uani 1 1 d . . . C32B C -0.16797(16) 1.02744(19) -0.19584(10) 0.0234(5) Uani 1 1 d . . . H32B H -0.1909 0.9630 -0.2127 0.028 Uiso 1 1 calc R . . C33B C -0.11610(15) 1.0264(2) -0.14279(10) 0.0226(5) Uani 1 1 d . . . H33B H -0.1036 0.9605 -0.1230 0.027 Uiso 1 1 calc R . . O1W O 1.10666(10) 1.11643(15) 0.53664(8) 0.0237(3) Uani 1 1 d . . . H11W H 1.0919 1.0899 0.5017 0.036 Uiso 1 1 d . . . H12W H 1.0883 1.1820 0.5346 0.036 Uiso 1 1 d . . . O2W O 0.95179(13) 1.2844(2) 0.10837(9) 0.0389(5) Uani 1 1 d . . . H21W H 0.9412 1.3428 0.0875 0.058 Uiso 1 1 d . . . H22W H 0.9296 1.3115 0.1354 0.058 Uiso 1 1 d . . . O3W O 1.10542(14) 1.33878(18) 0.03508(10) 0.0422(6) Uani 1 1 d . . . H31W H 1.0760 1.2982 0.0088 0.063 Uiso 1 1 d . . . H32W H 1.1363 1.2942 0.0576 0.063 Uiso 1 1 d . . . O4W O 0.69488(17) 1.2407(2) 0.17328(12) 0.0544(7) Uani 1 1 d . . . H41W H 0.7000 1.1938 0.2017 0.082 Uiso 1 1 d . . . H42W H 0.6828 1.1856 0.1502 0.082 Uiso 1 1 d . . . O5W O 1.0787(3) 1.2498(5) 0.1973(3) 0.0267(10) Uani 0.50 1 d PU A 1 H51W H 1.0753 1.2878 0.2263 0.040 Uiso 0.50 1 d P B 1 H52W H 1.0492 1.2813 0.1692 0.040 Uiso 0.50 1 d P C 1 O51W O 1.1015(4) 1.2268(7) 0.1894(4) 0.0528(18) Uani 0.50 1 d PU D 2 H53W H 1.0992 1.2151 0.2242 0.079 Uiso 0.50 1 d P E 2 H54W H 1.1551 1.2226 0.1898 0.079 Uiso 0.50 1 d P F 2 O34 O 0.93733(12) 0.82589(15) 0.45391(8) 0.0280(4) Uani 1 1 d . . . H34 H 0.9252 0.8427 0.4192 0.042 Uiso 1 1 d . . . C34 C 0.93351(16) 0.9094(3) 0.49425(13) 0.0337(6) Uani 1 1 d . . . H34A H 0.8931 0.8926 0.5158 0.040 Uiso 1 1 calc R . . H34B H 0.9210 0.9773 0.4736 0.040 Uiso 1 1 calc R . . H34C H 0.9839 0.9158 0.5211 0.040 Uiso 1 1 calc R . . O35 O 1.09608(12) 0.81331(17) 0.61829(10) 0.0335(4) Uani 1 1 d . . . H35 H 1.0742 0.8751 0.6150 0.050 Uiso 1 1 d . . . C35 C 1.0385(2) 0.7321(3) 0.60646(17) 0.0427(8) Uani 1 1 d . . . H35A H 1.0038 0.7377 0.6339 0.064 Uiso 1 1 calc R . . H35B H 1.0637 0.6616 0.6103 0.064 Uiso 1 1 calc R . . H35C H 1.0082 0.7408 0.5671 0.064 Uiso 1 1 calc R . . O36 O 0.73869(10) 1.09755(16) 0.26363(8) 0.0268(4) Uani 1 1 d . . . H36 H 0.7793 1.0503 0.2554 0.040 Uiso 1 1 d . . . C36 C 0.75444(16) 1.1289(3) 0.32259(12) 0.0304(5) Uani 1 1 d . . . H36A H 0.7107 1.1460 0.3319 0.046 Uiso 1 1 d . . . H36B H 0.7897 1.1798 0.3297 0.046 Uiso 1 1 d . . . H36C H 0.7711 1.0652 0.3469 0.046 Uiso 1 1 d . . . O37 O 0.84476(19) 1.3133(3) 0.18085(14) 0.0210(6) Uani 0.50 1 d P G 1 H37 H 0.8002 1.2989 0.1709 0.032 Uiso 0.50 1 d P H 1 O37A O 0.9407(3) 1.3350(4) 0.21567(19) 0.0397(10) Uani 0.50 1 d P G 2 H371 H 0.9842 1.3492 0.2413 0.059 Uiso 0.50 1 d P I 2 C37 C 0.88357(19) 1.2760(3) 0.23511(14) 0.0383(7) Uani 1 1 d . . . H37A H 0.9384 1.2976 0.2419 0.057 Uiso 0.50 1 calc PR G 1 H37B H 0.8801 1.1977 0.2362 0.057 Uiso 0.50 1 calc PR G 1 H37C H 0.8593 1.3068 0.2651 0.057 Uiso 0.50 1 calc PR G 1 H37D H 0.8884 1.2038 0.2248 0.057 Uiso 0.50 1 d PR G 2 H37E H 0.8329 1.3026 0.2176 0.057 Uiso 0.50 1 d PR G 2 H37F H 0.8900 1.2824 0.2762 0.057 Uiso 0.50 1 d PR G 2 O38 O 1.1986(2) 1.2756(3) 0.13545(16) 0.0259(7) Uani 0.50 1 d PU J 1 H38 H 1.1656 1.2460 0.1579 0.039 Uiso 0.50 1 d P K 1 C38 C 1.2560(4) 1.1891(6) 0.1357(3) 0.0289(13) Uani 0.50 1 d PU J 1 H38A H 1.2916 1.1867 0.1734 0.043 Uiso 0.50 1 calc PR J 1 H38B H 1.2856 1.2027 0.1056 0.043 Uiso 0.50 1 calc PR J 1 H38C H 1.2288 1.1203 0.1283 0.043 Uiso 0.50 1 calc PR J 1 O38A O 1.1932(4) 1.1745(6) 0.1111(3) 0.0185(12) Uani 0.25 1 d PU L 2 H381 H 1.1706 1.2023 0.1209 0.028 Uiso 0.25 1 d P M 2 C38A C 1.2822(7) 1.1815(13) 0.1313(7) 0.026(2) Uani 0.25 1 d PU L 2 H38D H 1.2960 1.2489 0.1522 0.039 Uiso 0.25 1 calc PR L 2 H38E H 1.3067 1.1790 0.0978 0.039 Uiso 0.25 1 calc PR L 2 H38F H 1.3007 1.1210 0.1569 0.039 Uiso 0.25 1 calc PR L 2 O38B O 1.1408(10) 1.1150(16) 0.1587(8) 0.094(5) Uani 0.25 1 d PU N 3 H382 H 1.1417 1.0702 0.1339 0.141 Uiso 0.25 1 d P O 3 C38B C 1.2270(11) 1.1801(15) 0.1359(9) 0.043(3) Uani 0.25 1 d PU N 3 H38G H 1.2222 1.1714 0.0943 0.065 Uiso 0.25 1 calc PR N 3 H38H H 1.2752 1.1460 0.1563 0.065 Uiso 0.25 1 calc PR N 3 H38I H 1.2283 1.2566 0.1455 0.065 Uiso 0.25 1 calc PR N 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 0.0141(6) 0.0127(7) 0.0219(7) 0.0021(6) 0.0038(6) 0.0010(5) O2 0.0135(6) 0.0138(7) 0.0190(7) -0.0004(6) 0.0008(5) 0.0010(5) O3 0.0169(7) 0.0088(6) 0.0218(7) -0.0009(5) 0.0025(6) -0.0009(5) O4 0.0110(6) 0.0188(8) 0.0358(9) -0.0059(7) 0.0044(6) -0.0027(6) N1 0.0110(7) 0.0102(7) 0.0176(8) -0.0008(6) 0.0030(6) -0.0018(6) N2 0.0104(7) 0.0120(8) 0.0201(8) 0.0018(6) -0.0001(6) -0.0008(6) C1 0.0114(7) 0.0124(8) 0.0148(8) -0.0019(7) 0.0021(7) -0.0009(7) C2 0.0115(7) 0.0131(8) 0.0124(8) -0.0008(7) 0.0017(7) 0.0007(7) C3 0.0138(8) 0.0101(8) 0.0127(8) 0.0002(6) 0.0015(7) -0.0003(7) C4 0.0137(8) 0.0103(8) 0.0143(8) -0.0009(7) 0.0015(7) -0.0017(7) C5 0.0123(8) 0.0111(8) 0.0141(8) -0.0019(7) 0.0015(7) -0.0010(7) C6 0.0126(8) 0.0101(8) 0.0152(8) -0.0007(7) 0.0023(7) -0.0008(7) C7 0.0127(8) 0.0117(8) 0.0139(8) -0.0008(7) 0.0015(7) -0.0015(7) C8 0.0109(7) 0.0095(8) 0.0132(8) -0.0005(6) 0.0019(7) -0.0012(6) C9 0.0130(8) 0.0130(9) 0.0170(9) -0.0014(7) 0.0026(7) -0.0034(7) C10 0.0129(8) 0.0119(9) 0.0258(10) -0.0035(8) 0.0038(8) -0.0020(7) C11 0.0134(8) 0.0124(9) 0.0165(9) -0.0010(7) 0.0013(7) -0.0009(7) C12 0.0156(9) 0.0132(9) 0.0291(11) -0.0006(8) 0.0054(8) 0.0024(8) C13 0.0149(8) 0.0153(9) 0.0223(10) 0.0005(8) 0.0042(8) 0.0015(7) C14 0.0129(8) 0.0146(9) 0.0188(9) -0.0019(7) 0.0045(7) -0.0014(7) C15 0.0126(8) 0.0139(9) 0.0253(10) -0.0003(8) 0.0033(8) -0.0002(7) C16 0.0162(9) 0.0190(10) 0.0165(9) 0.0011(8) -0.0020(8) -0.0014(8) C17 0.0151(8) 0.0144(9) 0.0146(8) -0.0008(7) -0.0013(7) -0.0023(7) C18 0.0130(8) 0.0103(8) 0.0138(8) -0.0006(7) 0.0012(7) -0.0020(7) C19 0.0141(8) 0.0165(9) 0.0137(8) -0.0003(7) 0.0032(7) 0.0000(7) C20 0.0159(8) 0.0159(9) 0.0148(9) 0.0027(7) 0.0041(7) -0.0009(7) C21 0.0101(7) 0.0127(9) 0.0177(9) 0.0028(7) 0.0012(7) -0.0013(7) C22 0.0130(8) 0.0177(10) 0.0263(11) -0.0022(8) 0.0018(8) -0.0003(8) C23 0.0197(9) 0.0118(9) 0.0282(11) -0.0006(8) 0.0032(9) -0.0026(8) O1A 0.0171(7) 0.0177(8) 0.0272(8) 0.0055(6) 0.0034(6) 0.0054(6) O2A 0.0125(6) 0.0159(7) 0.0300(8) 0.0012(6) -0.0008(6) 0.0026(6) O3A 0.0188(7) 0.0112(7) 0.0302(9) 0.0040(6) -0.0009(7) 0.0004(6) O4A 0.0129(6) 0.0184(7) 0.0224(7) -0.0008(6) 0.0024(6) -0.0010(6) N1A 0.0099(6) 0.0127(8) 0.0148(7) 0.0012(6) 0.0011(6) 0.0004(6) N2A 0.0116(7) 0.0199(9) 0.0196(8) 0.0072(7) 0.0011(7) 0.0002(7) C1A 0.0099(8) 0.0152(9) 0.0145(9) -0.0002(7) 0.0003(7) 0.0004(7) C2A 0.0138(8) 0.0159(9) 0.0153(9) 0.0001(7) 0.0006(7) 0.0014(7) C3A 0.0144(8) 0.0108(9) 0.0186(9) 0.0023(7) -0.0008(7) -0.0005(7) C4A 0.0144(8) 0.0133(9) 0.0179(9) 0.0025(7) 0.0004(7) -0.0017(7) C5A 0.0107(8) 0.0156(9) 0.0160(9) 0.0014(7) 0.0012(7) 0.0009(7) C6A 0.0130(8) 0.0110(8) 0.0125(8) 0.0007(7) 0.0022(7) 0.0002(7) C7A 0.0109(7) 0.0151(9) 0.0153(8) 0.0025(7) 0.0012(7) -0.0009(7) C8A 0.0102(7) 0.0142(9) 0.0141(8) 0.0026(7) 0.0028(7) 0.0008(7) C9A 0.0142(8) 0.0134(9) 0.0119(8) 0.0003(7) 0.0027(7) 0.0005(7) C10A 0.0184(9) 0.0135(9) 0.0155(9) 0.0004(7) 0.0039(7) 0.0007(7) C11A 0.0186(9) 0.0130(9) 0.0156(9) 0.0018(7) 0.0029(8) 0.0034(7) C12A 0.0208(10) 0.0217(11) 0.0372(13) 0.0034(10) 0.0076(10) 0.0091(9) C13A 0.0188(10) 0.0236(11) 0.0278(11) 0.0078(9) 0.0060(9) 0.0070(9) C14A 0.0114(8) 0.0273(12) 0.0211(10) 0.0029(9) 0.0043(8) 0.0038(8) C15A 0.0120(8) 0.0267(12) 0.0256(11) 0.0061(9) 0.0049(8) 0.0044(8) C16A 0.0122(8) 0.0246(11) 0.0176(9) 0.0042(8) 0.0002(7) -0.0016(8) C17A 0.0125(8) 0.0168(9) 0.0166(9) 0.0000(7) -0.0016(7) -0.0012(7) C18A 0.0141(8) 0.0176(9) 0.0165(9) 0.0023(7) 0.0029(7) 0.0039(8) C19A 0.0134(8) 0.0213(10) 0.0152(9) 0.0038(7) 0.0049(7) 0.0045(8) C20A 0.0139(8) 0.0231(11) 0.0182(9) 0.0076(8) 0.0049(8) 0.0009(8) C21A 0.0112(8) 0.0191(10) 0.0186(9) 0.0072(8) 0.0007(7) -0.0001(7) C22A 0.0137(8) 0.0215(11) 0.0268(11) -0.0052(9) 0.0055(8) -0.0006(8) C23A 0.0247(11) 0.0160(10) 0.0303(12) 0.0054(9) 0.0035(10) -0.0034(9) O1B 0.0207(7) 0.0190(8) 0.0228(8) -0.0038(6) 0.0047(6) -0.0004(6) O2B 0.0140(7) 0.0249(9) 0.0335(9) 0.0086(7) -0.0013(7) -0.0053(6) O3B 0.0205(7) 0.0204(8) 0.0249(8) 0.0010(7) -0.0005(7) -0.0041(7) O4B 0.0128(6) 0.0287(9) 0.0254(8) 0.0027(7) 0.0020(6) 0.0040(6) N1B 0.0109(7) 0.0192(9) 0.0171(8) 0.0009(7) 0.0030(6) -0.0004(6) N2B 0.0102(7) 0.0179(8) 0.0149(8) -0.0003(6) 0.0011(6) -0.0004(6) C1B 0.0109(8) 0.0232(11) 0.0202(10) 0.0057(8) -0.0004(8) -0.0019(8) C2B 0.0126(8) 0.0233(11) 0.0191(10) 0.0054(8) 0.0003(8) -0.0030(8) C3B 0.0159(9) 0.0190(10) 0.0156(9) 0.0025(8) -0.0005(8) -0.0039(8) C4B 0.0138(8) 0.0189(10) 0.0149(9) -0.0003(7) 0.0019(7) -0.0022(8) C5B 0.0118(8) 0.0171(9) 0.0144(9) 0.0002(7) 0.0020(7) -0.0004(7) C6B 0.0119(8) 0.0199(10) 0.0165(9) 0.0016(8) 0.0030(7) -0.0007(7) C7B 0.0108(7) 0.0165(9) 0.0142(8) -0.0003(7) 0.0012(7) 0.0011(7) C8B 0.0120(8) 0.0153(9) 0.0134(8) 0.0002(7) 0.0025(7) 0.0013(7) C9B 0.0163(9) 0.0228(11) 0.0136(9) 0.0015(8) 0.0034(7) 0.0037(8) C10B 0.0184(9) 0.0194(10) 0.0177(9) 0.0018(8) 0.0041(8) 0.0046(8) C11B 0.0185(9) 0.0178(10) 0.0150(9) 0.0001(7) 0.0030(8) 0.0021(8) C12B 0.0225(10) 0.0194(11) 0.0284(12) 0.0006(9) 0.0064(9) -0.0031(9) C13B 0.0172(9) 0.0220(11) 0.0203(10) -0.0022(8) 0.0033(8) -0.0043(8) C14B 0.0142(8) 0.0208(10) 0.0174(9) -0.0011(8) 0.0037(7) -0.0030(8) C15B 0.0120(8) 0.0207(10) 0.0202(10) 0.0004(8) 0.0020(8) -0.0032(8) C16B 0.0149(8) 0.0215(10) 0.0136(9) -0.0020(8) 0.0004(7) 0.0004(8) C17B 0.0127(8) 0.0187(10) 0.0149(9) -0.0005(7) 0.0023(7) -0.0007(7) C18B 0.0132(8) 0.0169(9) 0.0130(8) -0.0010(7) 0.0012(7) 0.0015(7) C19B 0.0139(8) 0.0195(10) 0.0146(9) 0.0016(7) 0.0048(7) -0.0008(8) C20B 0.0150(8) 0.0199(10) 0.0135(8) -0.0018(7) 0.0027(7) 0.0000(8) C21B 0.0107(7) 0.0168(9) 0.0132(8) -0.0024(7) 0.0007(7) 0.0008(7) C22B 0.0142(9) 0.0280(13) 0.0500(17) 0.0167(12) -0.0022(10) -0.0045(9) C23B 0.0254(11) 0.0200(11) 0.0348(14) -0.0020(10) 0.0038(11) -0.0033(9) O5 0.0175(7) 0.0205(8) 0.0297(9) -0.0033(7) 0.0012(7) -0.0067(6) O6 0.0354(11) 0.0281(11) 0.0625(15) 0.0265(10) -0.0156(11) -0.0124(9) O7 0.0167(7) 0.0208(8) 0.0268(8) -0.0008(7) 0.0018(6) 0.0021(6) O8 0.0339(9) 0.0186(8) 0.0193(8) -0.0009(6) -0.0045(7) 0.0077(7) O9 0.0272(9) 0.0328(10) 0.0253(9) -0.0070(8) -0.0033(7) -0.0054(8) O10 0.0257(9) 0.0367(11) 0.0221(8) 0.0077(8) -0.0038(7) -0.0006(8) N3 0.0176(8) 0.0167(9) 0.0165(8) 0.0029(7) -0.0027(7) 0.0004(7) N4 0.0174(8) 0.0314(11) 0.0172(8) -0.0008(8) 0.0010(7) -0.0025(8) C24 0.0157(9) 0.0162(10) 0.0308(12) 0.0039(9) 0.0005(9) -0.0029(8) C25 0.0146(8) 0.0168(10) 0.0178(9) 0.0012(8) -0.0027(7) -0.0037(8) C26 0.0142(8) 0.0169(9) 0.0202(10) -0.0001(8) 0.0004(8) 0.0003(8) C27 0.0144(8) 0.0175(10) 0.0147(9) 0.0014(7) 0.0030(7) 0.0012(7) C28 0.0147(8) 0.0180(10) 0.0150(9) 0.0004(7) 0.0029(7) -0.0004(7) C29 0.0171(9) 0.0165(10) 0.0199(10) -0.0007(8) 0.0012(8) 0.0002(8) C30 0.0159(9) 0.0195(10) 0.0206(10) -0.0024(8) 0.0021(8) -0.0021(8) C31 0.0150(8) 0.0239(11) 0.0139(9) 0.0012(8) 0.0014(7) -0.0019(8) C32 0.0265(11) 0.0164(10) 0.0208(10) 0.0051(8) -0.0045(9) 0.0009(9) C33 0.0271(11) 0.0149(10) 0.0216(10) 0.0020(8) -0.0029(9) 0.0006(9) O5A 0.0153(7) 0.0340(10) 0.0262(9) 0.0089(7) 0.0004(6) -0.0058(7) O6A 0.0168(7) 0.0366(10) 0.0240(8) 0.0053(7) -0.0001(6) 0.0018(7) O7A 0.0177(7) 0.0331(10) 0.0347(10) 0.0052(8) 0.0059(7) -0.0073(7) O8A 0.0217(7) 0.0172(8) 0.0239(8) -0.0048(6) 0.0020(6) 0.0032(6) O9A 0.0271(9) 0.0238(9) 0.0303(9) 0.0086(7) -0.0054(7) -0.0042(7) O10A 0.0317(9) 0.0254(9) 0.0252(9) -0.0057(7) -0.0035(7) 0.0123(8) N3A 0.0141(7) 0.0133(8) 0.0199(8) -0.0002(7) -0.0006(7) 0.0024(6) N4A 0.0203(8) 0.0137(8) 0.0222(9) -0.0017(7) -0.0070(7) -0.0003(7) C24A 0.0139(8) 0.0197(10) 0.0237(10) 0.0022(8) 0.0020(8) 0.0000(8) C25A 0.0134(8) 0.0136(9) 0.0209(10) 0.0006(7) -0.0006(7) -0.0003(7) C26A 0.0154(9) 0.0212(11) 0.0209(10) 0.0042(8) 0.0018(8) -0.0024(8) C27A 0.0105(7) 0.0154(9) 0.0189(9) -0.0026(7) 0.0018(7) -0.0002(7) C28A 0.0108(7) 0.0146(9) 0.0202(9) -0.0012(7) 0.0004(7) -0.0006(7) C29A 0.0160(9) 0.0210(10) 0.0175(9) -0.0044(8) 0.0002(8) 0.0026(8) C30A 0.0204(9) 0.0189(10) 0.0170(9) 0.0000(8) 0.0005(8) 0.0006(8) C31A 0.0138(8) 0.0129(9) 0.0190(9) -0.0024(7) -0.0023(7) -0.0004(7) C32A 0.0156(8) 0.0146(9) 0.0191(9) -0.0016(8) 0.0013(8) 0.0010(7) C33A 0.0138(8) 0.0131(9) 0.0183(9) 0.0007(7) 0.0022(7) 0.0003(7) O5B 0.0208(7) 0.0281(9) 0.0211(8) 0.0018(7) 0.0069(6) 0.0068(7) O6B 0.0275(10) 0.0717(17) 0.0321(11) -0.0193(11) -0.0103(8) 0.0244(11) O7B 0.0228(8) 0.0499(13) 0.0248(9) -0.0055(9) 0.0062(7) 0.0085(9) O8B 0.0294(9) 0.0255(9) 0.0227(8) 0.0018(7) 0.0002(7) -0.0086(8) O9B 0.0205(7) 0.0237(8) 0.0212(8) 0.0050(6) 0.0031(6) 0.0013(7) O10B 0.0294(9) 0.0250(9) 0.0207(8) -0.0022(7) 0.0014(7) -0.0076(7) N3B 0.0165(8) 0.0173(9) 0.0176(8) -0.0003(7) 0.0011(7) 0.0012(7) N4B 0.0166(8) 0.0218(9) 0.0168(8) 0.0002(7) 0.0057(7) -0.0020(7) C24B 0.0136(8) 0.0236(11) 0.0269(11) -0.0026(9) 0.0020(8) 0.0007(8) C25B 0.0167(9) 0.0196(10) 0.0182(9) -0.0012(8) 0.0005(8) 0.0020(8) C26B 0.0209(10) 0.0294(12) 0.0186(10) 0.0012(9) 0.0043(8) 0.0047(9) C27B 0.0169(9) 0.0187(10) 0.0165(9) -0.0008(8) 0.0038(8) 0.0028(8) C28B 0.0162(8) 0.0175(9) 0.0169(9) -0.0003(8) 0.0052(7) 0.0002(8) C29B 0.0213(10) 0.0149(10) 0.0206(10) -0.0010(8) 0.0031(8) 0.0006(8) C30B 0.0198(9) 0.0162(10) 0.0203(10) 0.0000(8) 0.0036(8) 0.0015(8) C31B 0.0171(9) 0.0197(10) 0.0143(9) -0.0014(8) 0.0040(7) -0.0011(8) C32B 0.0320(12) 0.0157(10) 0.0200(10) -0.0002(8) -0.0002(9) -0.0061(9) C33B 0.0305(12) 0.0165(10) 0.0184(10) 0.0025(8) -0.0004(9) -0.0034(9) O1W 0.0235(8) 0.0231(8) 0.0232(8) -0.0047(7) 0.0014(7) 0.0023(7) O2W 0.0405(11) 0.0419(12) 0.0333(11) 0.0013(9) 0.0051(9) 0.0114(10) O3W 0.0492(13) 0.0246(10) 0.0408(12) -0.0069(9) -0.0185(10) 0.0027(9) O4W 0.0604(17) 0.0530(16) 0.0498(15) -0.0104(12) 0.0114(13) -0.0163(13) O5W 0.021(2) 0.029(2) 0.032(2) -0.0015(17) 0.0086(18) 0.0091(17) O51W 0.045(4) 0.057(5) 0.051(4) 0.012(3) -0.002(3) -0.007(3) O34 0.0378(10) 0.0225(9) 0.0214(8) 0.0010(7) 0.0006(7) -0.0048(8) C34 0.0239(12) 0.0422(17) 0.0340(14) -0.0063(12) 0.0035(11) 0.0045(12) O35 0.0336(10) 0.0248(10) 0.0417(11) 0.0001(8) 0.0068(9) 0.0029(8) C35 0.0423(17) 0.0279(15) 0.059(2) 0.0071(14) 0.0137(16) 0.0006(13) O36 0.0198(8) 0.0307(10) 0.0279(9) 0.0003(7) 0.0003(7) 0.0009(7) C36 0.0284(12) 0.0336(14) 0.0295(13) 0.0011(11) 0.0070(10) -0.0033(11) O37 0.0175(14) 0.0241(17) 0.0211(15) 0.0022(13) 0.0032(12) -0.0035(13) O37A 0.047(3) 0.034(2) 0.034(2) 0.0001(18) -0.0027(19) -0.002(2) C37 0.0338(14) 0.0425(18) 0.0400(16) 0.0085(13) 0.0105(13) 0.0024(13) O38 0.0231(15) 0.0247(17) 0.0304(17) 0.0073(14) 0.0069(14) 0.0047(14) C38 0.013(3) 0.034(3) 0.037(3) 0.011(2) 0.000(3) 0.007(3) O38A 0.008(2) 0.022(3) 0.020(3) -0.001(2) -0.009(2) -0.002(2) C38A 0.012(4) 0.033(4) 0.032(4) 0.006(3) 0.000(4) 0.005(4) O38B 0.095(8) 0.096(8) 0.089(8) 0.005(7) 0.013(7) -0.005(7) C38B 0.041(5) 0.036(4) 0.048(4) 0.005(4) -0.002(4) 0.002(4) _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 1.429(3) . ? O1 C11 1.429(3) . ? O2 C2 1.368(2) . ? O2 C22 1.432(3) . ? O3 C3 1.369(3) . ? O3 C23 1.434(3) . ? O4 C9 1.224(3) . ? N1 C9 1.371(3) . ? N1 C6 1.415(3) . ? N1 C8 1.480(3) . ? N2 C15 1.506(3) . ? N2 C16 1.511(3) . ? N2 C21 1.534(3) . ? N2 H2 0.9300 . ? C1 C2 1.386(3) . ? C1 C6 1.395(3) . ? C1 H1 0.9500 . ? C2 C3 1.419(3) . ? C3 C4 1.391(3) . ? C4 C5 1.394(3) . ? C4 H4 0.9500 . ? C5 C6 1.383(3) . ? C5 C7 1.514(3) . ? C7 C17 1.543(3) . ? C7 C21 1.546(3) . ? C7 C8 1.563(3) . ? C8 C18 1.527(3) . ? C8 H8 1.0000 . ? C9 C10 1.516(3) . ? C10 C11 1.547(3) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C18 1.537(3) . ? C11 H11 1.0000 . ? C12 C13 1.503(3) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.336(3) . ? C13 H13 0.9500 . ? C14 C15 1.500(3) . ? C14 C19 1.518(3) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 C17 1.523(3) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 C19 1.536(3) . ? C18 H18 1.0000 . ? C19 C20 1.538(3) . ? C19 H19 1.0000 . ? C20 C21 1.518(3) . ? 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 . ? O1A C11A 1.430(3) . ? O1A C12A 1.439(3) . ? O2A C2A 1.371(3) . ? O2A C22A 1.424(3) . ? O3A C3A 1.366(3) . ? O3A C23A 1.430(3) . ? O4A C9A 1.226(3) . ? N1A C9A 1.377(3) . ? N1A C6A 1.422(3) . ? N1A C8A 1.486(3) . ? N2A C15A 1.504(3) . ? N2A C16A 1.517(3) . ? N2A C21A 1.538(3) . ? N2A H2A 0.9300 . ? C1A C2A 1.393(3) . ? C1A C6A 1.396(3) . ? C1A H1A 0.9500 . ? C2A C3A 1.418(3) . ? C3A C4A 1.385(3) . ? C4A C5A 1.397(3) . ? C4A H4A 0.9500 . ? C5A C6A 1.385(3) . ? C5A C7A 1.506(3) . ? C7A C21A 1.541(3) . ? C7A C17A 1.545(3) . ? C7A C8A 1.556(3) . ? C8A C18A 1.532(3) . ? C8A H8A 1.0000 . ? C9A C10A 1.515(3) . ? C10A C11A 1.548(3) . ? C10A H10C 0.9900 . ? C10A H10D 0.9900 . ? C11A C18A 1.530(3) . ? C11A H11A 1.0000 . ? C12A C13A 1.492(4) . ? C12A H12C 0.9900 . ? C12A H12D 0.9900 . ? C13A C14A 1.329(4) . ? C13A H13A 0.9500 . ? C14A C15A 1.500(4) . ? C14A C19A 1.523(3) . ? C15A H15C 0.9900 . ? C15A H15D 0.9900 . ? C16A C17A 1.520(3) . ? C16A H16C 0.9900 . ? C16A H16D 0.9900 . ? C17A H17C 0.9900 . ? C17A H17D 0.9900 . ? C18A C19A 1.533(3) . ? C18A H18A 1.0000 . ? C19A C20A 1.532(3) . ? C19A H19A 1.0000 . ? C20A C21A 1.518(3) . ? C20A H20C 0.9900 . ? C20A H20D 0.9900 . ? C21A H21A 1.0000 . ? C22A H22D 0.9800 . ? C22A H22E 0.9800 . ? C22A H22F 0.9800 . ? C23A H23D 0.9800 . ? C23A H23E 0.9800 . ? C23A H23F 0.9800 . ? O1B C11B 1.426(3) . ? O1B C12B 1.444(3) . ? O2B C2B 1.371(3) . ? O2B C22B 1.442(3) . ? O3B C3B 1.372(3) . ? O3B C23B 1.424(3) . ? O4B C9B 1.228(3) . ? N1B C9B 1.370(3) . ? N1B C6B 1.418(3) . ? N1B C8B 1.491(3) . ? N2B C16B 1.503(3) . ? N2B C15B 1.504(3) . ? N2B C21B 1.530(3) . ? N2B H2B 0.9300 . ? C1B C2B 1.385(4) . ? C1B C6B 1.395(3) . ? C1B H1B 0.9500 . ? C2B C3B 1.409(3) . ? C3B C4B 1.388(3) . ? C4B C5B 1.397(3) . ? C4B H4B 0.9500 . ? C5B C6B 1.390(3) . ? C5B C7B 1.511(3) . ? C7B C21B 1.543(3) . ? C7B C17B 1.544(3) . ? C7B C8B 1.559(3) . ? C8B C18B 1.530(3) . ? C8B H8B 1.0000 . ? C9B C10B 1.513(3) . ? C10B C11B 1.546(3) . ? C10B H10E 0.9900 . ? C10B H10F 0.9900 . ? C11B C18B 1.542(3) . ? C11B H11B 1.0000 . ? C12B C13B 1.495(4) . ? C12B H12E 0.9900 . ? C12B H12F 0.9900 . ? C13B C14B 1.337(3) . ? C13B H13B 0.9500 . ? C14B C15B 1.494(3) . ? C14B C19B 1.522(3) . ? C15B H15E 0.9900 . ? C15B H15F 0.9900 . ? C16B C17B 1.522(3) . ? C16B H16E 0.9900 . ? C16B H16F 0.9900 . ? C17B H17E 0.9900 . ? C17B H17F 0.9900 . ? C18B C19B 1.539(3) . ? C18B H18B 1.0000 . ? C19B C20B 1.526(3) . ? C19B H19B 1.0000 . ? C20B C21B 1.522(3) . ? C20B H20E 0.9900 . ? C20B H20F 0.9900 . ? C21B H21B 1.0000 . ? C22B H22G 0.9800 . ? C22B H22H 0.9800 . ? C22B H22I 0.9800 . ? C23B H23G 0.9800 . ? C23B H23H 0.9800 . ? C23B H23I 0.9800 . ? O5 C24 1.264(3) . ? O6 C24 1.244(3) . ? O7 C26 1.429(3) . ? O7 H7 1.0133 . ? O8 C27 1.229(3) . ? O9 N4 1.218(3) . ? O10 N4 1.232(3) . ? N3 C27 1.336(3) . ? N3 C25 1.453(3) . ? N3 H3 0.8800 . ? N4 C31 1.474(3) . ? C24 C25 1.536(3) . ? C25 C26 1.518(3) . ? C25 H25 1.0000 . ? C26 H26A 0.9900 . ? C26 H26B 0.9900 . ? C27 C28 1.508(3) . ? C28 C29 1.396(3) . ? C28 C33 1.397(3) . ? C29 C30 1.383(3) . ? C29 H29 0.9500 . ? C30 C31 1.381(3) . ? C30 H30 0.9500 . ? C31 C32 1.376(3) . ? C32 C33 1.386(3) . ? C32 H32 0.9500 . ? C33 H33 0.9500 . ? O5A C24A 1.274(3) . ? O6A C24A 1.240(3) . ? O7A C26A 1.423(3) . ? O7A H7A 0.8868 . ? O8A C27A 1.234(3) . ? O9A N4A 1.224(3) . ? O10A N4A 1.229(3) . ? N3A C27A 1.339(3) . ? N3A C25A 1.451(3) . ? N3A H3A 0.8800 . ? N4A C31A 1.471(3) . ? C24A C25A 1.548(3) . ? C25A C26A 1.519(3) . ? C25A H25A 1.0000 . ? C26A H26C 0.9900 . ? C26A H26D 0.9900 . ? C27A C28A 1.507(3) . ? C28A C29A 1.395(3) . ? C28A C33A 1.401(3) . ? C29A C30A 1.387(3) . ? C29A H29A 0.9500 . ? C30A C31A 1.389(3) . ? C30A H30A 0.9500 . ? C31A C32A 1.383(3) . ? C32A C33A 1.390(3) . ? C32A H32A 0.9500 . ? C33A H33A 0.9500 . ? O5B C24B 1.270(3) . ? O6B C24B 1.246(3) . ? O7B C26B 1.423(3) . ? O7B H7B 0.8202 . ? O8B C27B 1.235(3) . ? O9B N4B 1.229(3) . ? O10B N4B 1.226(3) . ? N3B C27B 1.334(3) . ? N3B C25B 1.451(3) . ? N3B H3B 0.8800 . ? N4B C31B 1.470(3) . ? C24B C25B 1.541(3) . ? C25B C26B 1.534(3) . ? C25B H25B 1.0000 . ? C26B H26E 0.9900 . ? C26B H26F 0.9900 . ? C27B C28B 1.502(3) . ? C28B C29B 1.398(3) . ? C28B C33B 1.399(3) . ? C29B C30B 1.382(3) . ? C29B H29B 0.9500 . ? C30B C31B 1.385(3) . ? C30B H30B 0.9500 . ? C31B C32B 1.386(3) . ? C32B C33B 1.392(3) . ? C32B H32B 0.9500 . ? C33B H33B 0.9500 . ? O1W H11W 0.8804 . ? O1W H12W 0.8777 . ? O2W H21W 0.8786 . ? O2W H22W 0.8835 . ? O3W H31W 0.8814 . ? O3W H32W 0.8774 . ? O4W H41W 0.8833 . ? O4W H42W 0.8761 . ? O5W H51W 0.8456 . ? O5W H52W 0.8505 . ? O5W H53W 0.7916 . ? O5W H54W 1.4312 . ? O51W H51W 1.3121 . ? O51W H52W 1.1631 . ? O51W H53W 0.8467 . ? O51W H54W 0.9409 . ? O34 C34 1.425(4) . ? O34 H34 0.8319 . ? C34 H34A 0.9800 . ? C34 H34B 0.9800 . ? C34 H34C 0.9800 . ? O35 C35 1.418(4) . ? O35 H35 0.8579 . ? C35 H35A 0.9800 . ? C35 H35B 0.9800 . ? C35 H35C 0.9800 . ? O36 C36 1.422(3) . ? O36 H36 0.9747 . ? C36 H36A 0.8683 . ? C36 H36B 0.8783 . ? C36 H36C 0.9903 . ? O37 C37 1.404(5) . ? O37 H37 0.7899 . ? O37 H37E 0.9447 . ? O37A C37 1.397(6) . ? O37A H371 0.8898 . ? C37 H37A 0.9800 . ? C37 H37B 0.9800 . ? C37 H37C 0.9800 . ? C37 H37D 0.9428 . ? C37 H37E 0.9599 . ? C37 H37F 0.9599 . ? O38 C38 1.476(8) . ? O38 H38 0.9399 . ? O38 H381 1.0623 . ? C38 H38A 0.9800 . ? C38 H38B 0.9800 . ? C38 H38C 0.9800 . ? C38 H381 1.4766 . ? O38A C38A 1.540(13) . ? O38A H381 0.6078 . ? C38A H38D 0.9800 . ? C38A H38E 0.9800 . ? C38A H38F 0.9800 . ? O38B C38B 1.89(3) . ? O38B H382 0.8148 . ? C38B H38 1.5303 . ? C38B H381 1.0196 . ? C38B H38G 0.9800 . ? C38B H38H 0.9800 . ? C38B H38I 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 C12 O1 C11 114.85(17) . . ? C2 O2 C22 115.98(17) . . ? C3 O3 C23 116.32(17) . . ? C9 N1 C6 123.55(17) . . ? C9 N1 C8 120.22(17) . . ? C6 N1 C8 109.36(16) . . ? C15 N2 C16 112.28(17) . . ? C15 N2 C21 113.61(17) . . ? C16 N2 C21 107.50(16) . . ? C15 N2 H2 107.7 . . ? C16 N2 H2 107.7 . . ? C21 N2 H2 107.7 . . ? C2 C1 C6 117.73(19) . . ? C2 C1 H1 121.1 . . ? C6 C1 H1 121.1 . . ? O2 C2 C1 123.35(18) . . ? O2 C2 C3 115.61(18) . . ? C1 C2 C3 121.04(18) . . ? O3 C3 C4 124.69(18) . . ? O3 C3 C2 115.47(18) . . ? C4 C3 C2 119.83(18) . . ? C3 C4 C5 119.05(19) . . ? C3 C4 H4 120.5 . . ? C5 C4 H4 120.5 . . ? C6 C5 C4 120.30(19) . . ? C6 C5 C7 110.35(18) . . ? C4 C5 C7 129.28(19) . . ? C5 C6 C1 122.02(19) . . ? C5 C6 N1 110.32(17) . . ? C1 C6 N1 127.62(18) . . ? C5 C7 C17 112.86(17) . . ? C5 C7 C21 114.38(17) . . ? C17 C7 C21 102.32(16) . . ? C5 C7 C8 102.08(16) . . ? C17 C7 C8 111.08(17) . . ? C21 C7 C8 114.51(17) . . ? N1 C8 C18 106.24(15) . . ? N1 C8 C7 104.48(15) . . ? C18 C8 C7 116.60(16) . . ? N1 C8 H8 109.7 . . ? C18 C8 H8 109.7 . . ? C7 C8 H8 109.7 . . ? O4 C9 N1 122.3(2) . . ? O4 C9 C10 121.30(19) . . ? N1 C9 C10 116.45(18) . . ? C9 C10 C11 117.61(18) . . ? 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 113.43(16) . . ? O1 C11 C10 104.16(17) . . ? C18 C11 C10 110.60(17) . . ? O1 C11 H11 109.5 . . ? C18 C11 H11 109.5 . . ? C10 C11 H11 109.5 . . ? O1 C12 C13 112.19(18) . . ? O1 C12 H12A 109.2 . . ? C13 C12 H12A 109.2 . . ? O1 C12 H12B 109.2 . . ? C13 C12 H12B 109.2 . . ? H12A C12 H12B 107.9 . . ? C14 C13 C12 123.5(2) . . ? C14 C13 H13 118.3 . . ? C12 C13 H13 118.3 . . ? C13 C14 C15 120.6(2) . . ? C13 C14 C19 123.64(19) . . ? C15 C14 C19 115.74(19) . . ? C14 C15 N2 109.36(17) . . ? C14 C15 H15A 109.8 . . ? N2 C15 H15A 109.8 . . ? C14 C15 H15B 109.8 . . ? N2 C15 H15B 109.8 . . ? H15A C15 H15B 108.3 . . ? N2 C16 C17 105.53(17) . . ? N2 C16 H16A 110.6 . . ? C17 C16 H16A 110.6 . . ? N2 C16 H16B 110.6 . . ? C17 C16 H16B 110.6 . . ? H16A C16 H16B 108.8 . . ? C16 C17 C7 103.70(17) . . ? C16 C17 H17A 111.0 . . ? C7 C17 H17A 111.0 . . ? C16 C17 H17B 111.0 . . ? C7 C17 H17B 111.0 . . ? H17A C17 H17B 109.0 . . ? C8 C18 C19 112.42(16) . . ? C8 C18 C11 106.63(16) . . ? C19 C18 C11 118.26(17) . . ? C8 C18 H18 106.3 . . ? C19 C18 H18 106.3 . . ? C11 C18 H18 106.3 . . ? C14 C19 C18 114.19(17) . . ? C14 C19 C20 109.34(17) . . ? C18 C19 C20 106.07(17) . . ? C14 C19 H19 109.0 . . ? C18 C19 H19 109.0 . . ? C20 C19 H19 109.0 . . ? C21 C20 C19 108.28(17) . . ? 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 110.44(17) . . ? C20 C21 C7 115.40(17) . . ? N2 C21 C7 105.15(16) . . ? 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 . . ? C11A O1A C12A 114.91(18) . . ? C2A O2A C22A 116.55(18) . . ? C3A O3A C23A 116.17(18) . . ? C9A N1A C6A 125.29(17) . . ? C9A N1A C8A 118.88(17) . . ? C6A N1A C8A 109.31(16) . . ? C15A N2A C16A 112.84(18) . . ? C15A N2A C21A 113.23(18) . . ? C16A N2A C21A 107.52(16) . . ? C15A N2A H2A 107.7 . . ? C16A N2A H2A 107.7 . . ? C21A N2A H2A 107.7 . . ? C2A C1A C6A 117.37(19) . . ? C2A C1A H1A 121.3 . . ? C6A C1A H1A 121.3 . . ? O2A C2A C1A 124.06(19) . . ? O2A C2A C3A 114.60(19) . . ? C1A C2A C3A 121.34(19) . . ? O3A C3A C4A 125.17(19) . . ? O3A C3A C2A 115.13(18) . . ? C4A C3A C2A 119.66(19) . . ? C3A C4A C5A 119.22(19) . . ? C3A C4A H4A 120.4 . . ? C5A C4A H4A 120.4 . . ? C6A C5A C4A 120.27(19) . . ? C6A C5A C7A 110.21(18) . . ? C4A C5A C7A 129.25(19) . . ? C5A C6A C1A 121.90(19) . . ? C5A C6A N1A 109.98(17) . . ? C1A C6A N1A 128.10(18) . . ? C5A C7A C21A 115.15(17) . . ? C5A C7A C17A 112.18(18) . . ? C21A C7A C17A 101.89(16) . . ? C5A C7A C8A 102.63(16) . . ? C21A C7A C8A 114.53(18) . . ? C17A C7A C8A 110.79(17) . . ? N1A C8A C18A 106.60(16) . . ? N1A C8A C7A 104.26(16) . . ? C18A C8A C7A 116.76(17) . . ? N1A C8A H8A 109.6 . . ? C18A C8A H8A 109.6 . . ? C7A C8A H8A 109.6 . . ? O4A C9A N1A 122.7(2) . . ? O4A C9A C10A 122.8(2) . . ? N1A C9A C10A 114.44(17) . . ? C9A C10A C11A 117.13(18) . . ? C9A C10A H10C 108.0 . . ? C11A C10A H10C 108.0 . . ? C9A C10A H10D 108.0 . . ? C11A C10A H10D 108.0 . . ? H10C C10A H10D 107.3 . . ? O1A C11A C18A 114.80(18) . . ? O1A C11A C10A 104.22(17) . . ? C18A C11A C10A 110.18(17) . . ? O1A C11A H11A 109.2 . . ? C18A C11A H11A 109.2 . . ? C10A C11A H11A 109.2 . . ? O1A C12A C13A 111.4(2) . . ? O1A C12A H12C 109.4 . . ? C13A C12A H12C 109.4 . . ? O1A C12A H12D 109.4 . . ? C13A C12A H12D 109.4 . . ? H12C C12A H12D 108.0 . . ? C14A C13A C12A 121.7(2) . . ? C14A C13A H13A 119.1 . . ? C12A C13A H13A 119.1 . . ? C13A C14A C15A 121.4(2) . . ? C13A C14A C19A 122.5(2) . . ? C15A C14A C19A 116.1(2) . . ? C14A C15A N2A 111.04(18) . . ? C14A C15A H15C 109.4 . . ? N2A C15A H15C 109.4 . . ? C14A C15A H15D 109.4 . . ? N2A C15A H15D 109.4 . . ? H15C C15A H15D 108.0 . . ? N2A C16A C17A 104.52(17) . . ? N2A C16A H16C 110.8 . . ? C17A C16A H16C 110.8 . . ? N2A C16A H16D 110.8 . . ? C17A C16A H16D 110.8 . . ? H16C C16A H16D 108.9 . . ? C16A C17A C7A 103.11(18) . . ? C16A C17A H17C 111.1 . . ? C7A C17A H17C 111.1 . . ? C16A C17A H17D 111.1 . . ? C7A C17A H17D 111.1 . . ? H17C C17A H17D 109.1 . . ? C11A C18A C8A 107.55(17) . . ? C11A C18A C19A 118.30(18) . . ? C8A C18A C19A 112.72(18) . . ? C11A C18A H18A 105.8 . . ? C8A C18A H18A 105.8 . . ? C19A C18A H18A 105.8 . . ? C14A C19A C20A 108.87(19) . . ? C14A C19A C18A 114.48(18) . . ? C20A C19A C18A 106.97(17) . . ? C14A C19A H19A 108.8 . . ? C20A C19A H19A 108.8 . . ? C18A C19A H19A 108.8 . . ? C21A C20A C19A 108.96(18) . . ? C21A C20A H20C 109.9 . . ? C19A C20A H20C 109.9 . . ? C21A C20A H20D 109.9 . . ? C19A C20A H20D 109.9 . . ? H20C C20A H20D 108.3 . . ? C20A C21A N2A 110.74(18) . . ? C20A C21A C7A 115.09(18) . . ? N2A C21A C7A 104.66(16) . . ? C20A C21A H21A 108.7 . . ? N2A C21A H21A 108.7 . . ? C7A C21A H21A 108.7 . . ? O2A C22A H22D 109.5 . . ? O2A C22A H22E 109.5 . . ? H22D C22A H22E 109.5 . . ? O2A C22A H22F 109.5 . . ? H22D C22A H22F 109.5 . . ? H22E C22A H22F 109.5 . . ? O3A C23A H23D 109.5 . . ? O3A C23A H23E 109.5 . . ? H23D C23A H23E 109.5 . . ? O3A C23A H23F 109.5 . . ? H23D C23A H23F 109.5 . . ? H23E C23A H23F 109.5 . . ? C11B O1B C12B 115.94(18) . . ? C2B O2B C22B 116.9(2) . . ? C3B O3B C23B 117.12(19) . . ? C9B N1B C6B 125.11(19) . . ? C9B N1B C8B 118.46(18) . . ? C6B N1B C8B 109.06(17) . . ? C16B N2B C15B 113.10(18) . . ? C16B N2B C21B 107.76(15) . . ? C15B N2B C21B 113.49(16) . . ? C16B N2B H2B 107.4 . . ? C15B N2B H2B 107.4 . . ? C21B N2B H2B 107.4 . . ? C2B C1B C6B 117.4(2) . . ? C2B C1B H1B 121.3 . . ? C6B C1B H1B 121.3 . . ? O2B C2B C1B 123.9(2) . . ? O2B C2B C3B 114.7(2) . . ? C1B C2B C3B 121.4(2) . . ? O3B C3B C4B 124.3(2) . . ? O3B C3B C2B 115.3(2) . . ? C4B C3B C2B 120.5(2) . . ? C3B C4B C5B 118.4(2) . . ? C3B C4B H4B 120.8 . . ? C5B C4B H4B 120.8 . . ? C6B C5B C4B 120.35(19) . . ? C6B C5B C7B 110.22(19) . . ? C4B C5B C7B 129.30(19) . . ? C5B C6B C1B 121.9(2) . . ? C5B C6B N1B 110.11(18) . . ? C1B C6B N1B 128.0(2) . . ? C5B C7B C21B 115.40(17) . . ? C5B C7B C17B 113.18(18) . . ? C21B C7B C17B 101.61(16) . . ? C5B C7B C8B 102.24(16) . . ? C21B C7B C8B 114.39(18) . . ? C17B C7B C8B 110.38(17) . . ? N1B C8B C18B 106.31(16) . . ? N1B C8B C7B 104.21(17) . . ? C18B C8B C7B 116.19(17) . . ? N1B C8B H8B 109.9 . . ? C18B C8B H8B 109.9 . . ? C7B C8B H8B 109.9 . . ? O4B C9B N1B 123.1(2) . . ? O4B C9B C10B 122.4(2) . . ? N1B C9B C10B 114.45(19) . . ? C9B C10B C11B 116.18(19) . . ? C9B C10B H10E 108.2 . . ? C11B C10B H10E 108.2 . . ? C9B C10B H10F 108.2 . . ? C11B C10B H10F 108.2 . . ? H10E C10B H10F 107.4 . . ? O1B C11B C18B 115.55(18) . . ? O1B C11B C10B 103.82(17) . . ? C18B C11B C10B 110.36(18) . . ? O1B C11B H11B 109.0 . . ? C18B C11B H11B 109.0 . . ? C10B C11B H11B 109.0 . . ? O1B C12B C13B 109.7(2) . . ? O1B C12B H12E 109.7 . . ? C13B C12B H12E 109.7 . . ? O1B C12B H12F 109.7 . . ? C13B C12B H12F 109.7 . . ? H12E C12B H12F 108.2 . . ? C14B C13B C12B 120.8(2) . . ? C14B C13B H13B 119.6 . . ? C12B C13B H13B 119.6 . . ? C13B C14B C15B 122.1(2) . . ? C13B C14B C19B 121.9(2) . . ? C15B C14B C19B 116.0(2) . . ? C14B C15B N2B 111.69(17) . . ? C14B C15B H15E 109.3 . . ? N2B C15B H15E 109.3 . . ? C14B C15B H15F 109.3 . . ? N2B C15B H15F 109.3 . . ? H15E C15B H15F 107.9 . . ? N2B C16B C17B 104.81(17) . . ? N2B C16B H16E 110.8 . . ? C17B C16B H16E 110.8 . . ? N2B C16B H16F 110.8 . . ? C17B C16B H16F 110.8 . . ? H16E C16B H16F 108.9 . . ? C16B C17B C7B 102.53(17) . . ? C16B C17B H17E 111.3 . . ? C7B C17B H17E 111.3 . . ? C16B C17B H17F 111.3 . . ? C7B C17B H17F 111.3 . . ? H17E C17B H17F 109.2 . . ? C8B C18B C19B 112.89(17) . . ? C8B C18B C11B 107.74(17) . . ? C19B C18B C11B 118.01(18) . . ? C8B C18B H18B 105.8 . . ? C19B C18B H18B 105.8 . . ? C11B C18B H18B 105.8 . . ? C14B C19B C20B 109.18(18) . . ? C14B C19B C18B 113.81(18) . . ? C20B C19B C18B 107.01(17) . . ? C14B C19B H19B 108.9 . . ? C20B C19B H19B 108.9 . . ? C18B C19B H19B 108.9 . . ? C21B C20B C19B 109.17(17) . . ? C21B C20B H20E 109.8 . . ? C19B C20B H20E 109.8 . . ? C21B C20B H20F 109.8 . . ? C19B C20B H20F 109.8 . . ? H20E C20B H20F 108.3 . . ? C20B C21B N2B 110.77(17) . . ? C20B C21B C7B 114.88(17) . . ? N2B C21B C7B 104.43(16) . . ? C20B C21B H21B 108.9 . . ? N2B C21B H21B 108.9 . . ? C7B C21B H21B 108.9 . . ? O2B C22B H22G 109.5 . . ? O2B C22B H22H 109.5 . . ? H22G C22B H22H 109.5 . . ? O2B C22B H22I 109.5 . . ? H22G C22B H22I 109.5 . . ? H22H C22B H22I 109.5 . . ? O3B C23B H23G 109.5 . . ? O3B C23B H23H 109.5 . . ? H23G C23B H23H 109.5 . . ? O3B C23B H23I 109.5 . . ? H23G C23B H23I 109.5 . . ? H23H C23B H23I 109.5 . . ? C26 O7 H7 100.8 . . ? C27 N3 C25 121.04(19) . . ? C27 N3 H3 119.5 . . ? C25 N3 H3 119.5 . . ? O9 N4 O10 124.3(2) . . ? O9 N4 C31 118.1(2) . . ? O10 N4 C31 117.7(2) . . ? O6 C24 O5 125.7(2) . . ? O6 C24 C25 119.4(2) . . ? O5 C24 C25 114.8(2) . . ? N3 C25 C26 112.67(18) . . ? N3 C25 C24 110.26(18) . . ? C26 C25 C24 112.79(19) . . ? N3 C25 H25 106.9 . . ? C26 C25 H25 106.9 . . ? C24 C25 H25 106.9 . . ? O7 C26 C25 110.03(18) . . ? O7 C26 H26A 109.7 . . ? C25 C26 H26A 109.7 . . ? O7 C26 H26B 109.7 . . ? C25 C26 H26B 109.7 . . ? H26A C26 H26B 108.2 . . ? O8 C27 N3 122.3(2) . . ? O8 C27 C28 120.3(2) . . ? N3 C27 C28 117.42(19) . . ? C29 C28 C33 119.4(2) . . ? C29 C28 C27 117.5(2) . . ? C33 C28 C27 123.1(2) . . ? C30 C29 C28 120.8(2) . . ? C30 C29 H29 119.6 . . ? C28 C29 H29 119.6 . . ? C31 C30 C29 118.1(2) . . ? C31 C30 H30 121.0 . . ? C29 C30 H30 121.0 . . ? C32 C31 C30 122.9(2) . . ? C32 C31 N4 118.2(2) . . ? C30 C31 N4 118.9(2) . . ? C31 C32 C33 118.6(2) . . ? C31 C32 H32 120.7 . . ? C33 C32 H32 120.7 . . ? C32 C33 C28 120.3(2) . . ? C32 C33 H33 119.9 . . ? C28 C33 H33 119.9 . . ? C26A O7A H7A 117.9 . . ? C27A N3A C25A 124.35(19) . . ? C27A N3A H3A 117.8 . . ? C25A N3A H3A 117.8 . . ? O9A N4A O10A 124.7(2) . . ? O9A N4A C31A 117.4(2) . . ? O10A N4A C31A 117.8(2) . . ? O6A C24A O5A 124.6(2) . . ? O6A C24A C25A 118.8(2) . . ? O5A C24A C25A 116.53(19) . . ? N3A C25A C26A 111.32(18) . . ? N3A C25A C24A 110.84(18) . . ? C26A C25A C24A 112.18(18) . . ? N3A C25A H25A 107.4 . . ? C26A C25A H25A 107.4 . . ? C24A C25A H25A 107.4 . . ? O7A C26A C25A 109.78(19) . . ? O7A C26A H26C 109.7 . . ? C25A C26A H26C 109.7 . . ? O7A C26A H26D 109.7 . . ? C25A C26A H26D 109.7 . . ? H26C C26A H26D 108.2 . . ? O8A C27A N3A 123.8(2) . . ? O8A C27A C28A 121.18(19) . . ? N3A C27A C28A 115.01(19) . . ? C29A C28A C33A 119.2(2) . . ? C29A C28A C27A 120.24(19) . . ? C33A C28A C27A 120.53(19) . . ? C30A C29A C28A 120.6(2) . . ? C30A C29A H29A 119.7 . . ? C28A C29A H29A 119.7 . . ? C29A C30A C31A 118.6(2) . . ? C29A C30A H30A 120.7 . . ? C31A C30A H30A 120.7 . . ? C32A C31A C30A 122.5(2) . . ? C32A C31A N4A 117.5(2) . . ? C30A C31A N4A 120.0(2) . . ? C31A C32A C33A 118.2(2) . . ? C31A C32A H32A 120.9 . . ? C33A C32A H32A 120.9 . . ? C32A C33A C28A 120.9(2) . . ? C32A C33A H33A 119.6 . . ? C28A C33A H33A 119.6 . . ? C26B O7B H7B 104.8 . . ? C27B N3B C25B 121.68(19) . . ? C27B N3B H3B 119.2 . . ? C25B N3B H3B 119.2 . . ? O10B N4B O9B 123.77(19) . . ? O10B N4B C31B 118.3(2) . . ? O9B N4B C31B 117.96(19) . . ? O6B C24B O5B 124.6(2) . . ? O6B C24B C25B 117.0(2) . . ? O5B C24B C25B 118.4(2) . . ? N3B C25B C26B 111.30(18) . . ? N3B C25B C24B 112.29(18) . . ? C26B C25B C24B 110.2(2) . . ? N3B C25B H25B 107.6 . . ? C26B C25B H25B 107.6 . . ? C24B C25B H25B 107.6 . . ? O7B C26B C25B 112.1(2) . . ? O7B C26B H26E 109.2 . . ? C25B C26B H26E 109.2 . . ? O7B C26B H26F 109.2 . . ? C25B C26B H26F 109.2 . . ? H26E C26B H26F 107.9 . . ? O8B C27B N3B 123.6(2) . . ? O8B C27B C28B 119.0(2) . . ? N3B C27B C28B 117.3(2) . . ? C29B C28B C33B 119.2(2) . . ? C29B C28B C27B 116.9(2) . . ? C33B C28B C27B 123.9(2) . . ? C30B C29B C28B 120.8(2) . . ? C30B C29B H29B 119.6 . . ? C28B C29B H29B 119.6 . . ? C29B C30B C31B 118.5(2) . . ? C29B C30B H30B 120.8 . . ? C31B C30B H30B 120.8 . . ? C30B C31B C32B 122.6(2) . . ? C30B C31B N4B 118.4(2) . . ? C32B C31B N4B 118.9(2) . . ? C31B C32B C33B 118.2(2) . . ? C31B C32B H32B 120.9 . . ? C33B C32B H32B 120.9 . . ? C32B C33B C28B 120.7(2) . . ? C32B C33B H33B 119.7 . . ? C28B C33B H33B 119.7 . . ? H11W O1W H12W 105.3 . . ? H21W O2W H22W 91.0 . . ? H31W O3W H32W 105.3 . . ? H41W O4W H42W 86.0 . . ? H51W O5W H52W 104.1 . . ? H51W O5W H53W 75.6 . . ? H52W O5W H53W 169.6 . . ? H51W O5W H54W 117.3 . . ? H52W O5W H54W 116.6 . . ? H53W O5W H54W 71.8 . . ? H51W O51W H52W 65.1 . . ? H51W O51W H53W 49.9 . . ? H52W O51W H53W 107.9 . . ? H51W O51W H54W 120.8 . . ? H52W O51W H54W 137.9 . . ? H53W O51W H54W 103.2 . . ? C34 O34 H34 116.1 . . ? O34 C34 H34A 109.5 . . ? O34 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? O34 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? C35 O35 H35 109.7 . . ? 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 111.1 . . ? O36 C36 H36A 108.3 . . ? O36 C36 H36B 112.0 . . ? H36A C36 H36B 113.6 . . ? O36 C36 H36C 108.9 . . ? H36A C36 H36C 102.7 . . ? H36B C36 H36C 110.9 . . ? C37 O37 H37 117.5 . . ? C37 O37 H37E 42.9 . . ? H37 O37 H37E 81.4 . . ? C37 O37A H371 117.1 . . ? O37A C37 O37 76.7(3) . . ? O37A C37 H37A 33.0 . . ? O37 C37 H37A 109.5 . . ? O37A C37 H37B 125.9 . . ? O37 C37 H37B 109.5 . . ? H37A C37 H37B 109.5 . . ? O37A C37 H37C 118.8 . . ? O37 C37 H37C 109.5 . . ? H37A C37 H37C 109.5 . . ? H37B C37 H37C 109.5 . . ? O37A C37 H37D 108.0 . . ? O37 C37 H37D 97.6 . . ? H37A C37 H37D 99.6 . . ? H37B C37 H37D 20.3 . . ? H37C C37 H37D 129.7 . . ? O37A C37 H37E 109.9 . . ? O37 C37 H37E 42.1 . . ? H37A C37 H37E 140.1 . . ? H37B C37 H37E 107.4 . . ? H37C C37 H37E 71.1 . . ? H37D C37 H37E 110.1 . . ? O37A C37 H37F 110.4 . . ? O37 C37 H37F 146.6 . . ? H37A C37 H37F 84.6 . . ? H37B C37 H37F 92.9 . . ? H37C C37 H37F 37.7 . . ? H37D C37 H37F 110.1 . . ? H37E C37 H37F 108.4 . . ? C38 O38 H38 102.1 . . ? C38 O38 H381 69.0 . . ? H38 O38 H381 63.0 . . ? O38 C38 H38A 109.5 . . ? O38 C38 H38B 109.5 . . ? H38A C38 H38B 109.5 . . ? O38 C38 H38C 109.5 . . ? H38A C38 H38C 109.5 . . ? H38B C38 H38C 109.5 . . ? O38 C38 H381 42.2 . . ? H38A C38 H381 130.3 . . ? H38B C38 H381 118.2 . . ? H38C C38 H381 67.8 . . ? C38A O38A H381 123.4 . . ? O38A C38A H38D 109.5 . . ? O38A C38A H38E 109.5 . . ? H38D C38A H38E 109.5 . . ? O38A C38A H38F 109.5 . . ? H38D C38A H38F 109.5 . . ? H38E C38A H38F 109.5 . . ? C38B O38B H382 87.2 . . ? O38B C38B H38 58.1 . . ? O38B C38B H381 55.9 . . ? H38 C38B H381 43.2 . . ? O38B C38B H38G 109.5 . . ? H38 C38B H38G 118.9 . . ? H381 C38B H38G 78.6 . . ? O38B C38B H38H 109.5 . . ? H38 C38B H38H 131.5 . . ? H381 C38B H38H 165.4 . . ? H38G C38B H38H 109.5 . . ? O38B C38B H38I 109.5 . . ? H38 C38B H38I 51.8 . . ? H381 C38B H38I 77.8 . . ? H38G C38B H38I 109.5 . . ? H38H C38B H38I 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 -10.8(3) . . . . ? C22 O2 C2 C3 169.74(18) . . . . ? C6 C1 C2 O2 -178.91(18) . . . . ? C6 C1 C2 C3 0.6(3) . . . . ? C23 O3 C3 C4 -2.4(3) . . . . ? C23 O3 C3 C2 177.06(18) . . . . ? O2 C2 C3 O3 -1.7(3) . . . . ? C1 C2 C3 O3 178.78(19) . . . . ? O2 C2 C3 C4 177.83(18) . . . . ? C1 C2 C3 C4 -1.7(3) . . . . ? O3 C3 C4 C5 -179.12(19) . . . . ? C2 C3 C4 C5 1.4(3) . . . . ? C3 C4 C5 C6 0.0(3) . . . . ? C3 C4 C5 C7 -176.6(2) . . . . ? C4 C5 C6 C1 -1.1(3) . . . . ? C7 C5 C6 C1 176.04(19) . . . . ? C4 C5 C6 N1 177.04(19) . . . . ? C7 C5 C6 N1 -5.8(2) . . . . ? C2 C1 C6 C5 0.8(3) . . . . ? C2 C1 C6 N1 -177.0(2) . . . . ? C9 N1 C6 C5 -157.64(19) . . . . ? C8 N1 C6 C5 -6.8(2) . . . . ? C9 N1 C6 C1 20.4(3) . . . . ? C8 N1 C6 C1 171.2(2) . . . . ? C6 C5 C7 C17 -104.4(2) . . . . ? C4 C5 C7 C17 72.5(3) . . . . ? C6 C5 C7 C21 139.20(18) . . . . ? C4 C5 C7 C21 -44.0(3) . . . . ? C6 C5 C7 C8 14.9(2) . . . . ? C4 C5 C7 C8 -168.2(2) . . . . ? C9 N1 C8 C18 44.0(2) . . . . ? C6 N1 C8 C18 -108.01(18) . . . . ? C9 N1 C8 C7 167.80(18) . . . . ? C6 N1 C8 C7 15.8(2) . . . . ? C5 C7 C8 N1 -17.96(19) . . . . ? C17 C7 C8 N1 102.60(18) . . . . ? C21 C7 C8 N1 -142.12(17) . . . . ? C5 C7 C8 C18 98.94(19) . . . . ? C17 C7 C8 C18 -140.51(18) . . . . ? C21 C7 C8 C18 -25.2(2) . . . . ? C6 N1 C9 O4 -26.3(3) . . . . ? C8 N1 C9 O4 -174.1(2) . . . . ? C6 N1 C9 C10 154.0(2) . . . . ? C8 N1 C9 C10 6.2(3) . . . . ? O4 C9 C10 C11 151.1(2) . . . . ? N1 C9 C10 C11 -29.2(3) . . . . ? C12 O1 C11 C18 -70.6(2) . . . . ? C12 O1 C11 C10 169.07(17) . . . . ? C9 C10 C11 O1 121.5(2) . . . . ? C9 C10 C11 C18 -0.7(3) . . . . ? C11 O1 C12 C13 86.5(2) . . . . ? O1 C12 C13 C14 -62.2(3) . . . . ? C12 C13 C14 C15 176.7(2) . . . . ? C12 C13 C14 C19 -1.3(3) . . . . ? C13 C14 C15 N2 -123.1(2) . . . . ? C19 C14 C15 N2 55.1(2) . . . . ? C16 N2 C15 C14 76.7(2) . . . . ? C21 N2 C15 C14 -45.5(2) . . . . ? C15 N2 C16 C17 -139.39(17) . . . . ? C21 N2 C16 C17 -13.7(2) . . . . ? N2 C16 C17 C7 33.5(2) . . . . ? C5 C7 C17 C16 -163.37(17) . . . . ? C21 C7 C17 C16 -40.0(2) . . . . ? C8 C7 C17 C16 82.7(2) . . . . ? N1 C8 C18 C19 157.17(16) . . . . ? C7 C8 C18 C19 41.3(2) . . . . ? N1 C8 C18 C11 -71.70(19) . . . . ? C7 C8 C18 C11 172.38(16) . . . . ? O1 C11 C18 C8 -67.2(2) . . . . ? C10 C11 C18 C8 49.4(2) . . . . ? O1 C11 C18 C19 60.5(2) . . . . ? C10 C11 C18 C19 177.15(17) . . . . ? C13 C14 C19 C18 55.1(3) . . . . ? C15 C14 C19 C18 -123.1(2) . . . . ? C13 C14 C19 C20 173.7(2) . . . . ? C15 C14 C19 C20 -4.4(2) . . . . ? C8 C18 C19 C14 57.8(2) . . . . ? C11 C18 C19 C14 -67.2(2) . . . . ? C8 C18 C19 C20 -62.7(2) . . . . ? C11 C18 C19 C20 172.32(17) . . . . ? C14 C19 C20 C21 -54.1(2) . . . . ? C18 C19 C20 C21 69.4(2) . . . . ? C19 C20 C21 N2 63.1(2) . . . . ? C19 C20 C21 C7 -56.0(2) . . . . ? C15 N2 C21 C20 -11.6(2) . . . . ? C16 N2 C21 C20 -136.43(18) . . . . ? C15 N2 C21 C7 113.54(19) . . . . ? C16 N2 C21 C7 -11.3(2) . . . . ? C5 C7 C21 C20 -84.3(2) . . . . ? C17 C7 C21 C20 153.32(18) . . . . ? C8 C7 C21 C20 33.0(2) . . . . ? C5 C7 C21 N2 153.76(17) . . . . ? C17 C7 C21 N2 31.4(2) . . . . ? C8 C7 C21 N2 -88.90(19) . . . . ? C22A O2A C2A C1A 1.9(3) . . . . ? C22A O2A C2A C3A -178.14(19) . . . . ? C6A C1A C2A O2A -178.11(19) . . . . ? C6A C1A C2A C3A 1.9(3) . . . . ? C23A O3A C3A C4A 2.0(3) . . . . ? C23A O3A C3A C2A 179.9(2) . . . . ? O2A C2A C3A O3A -2.5(3) . . . . ? C1A C2A C3A O3A 177.5(2) . . . . ? O2A C2A C3A C4A 175.6(2) . . . . ? C1A C2A C3A C4A -4.5(3) . . . . ? O3A C3A C4A C5A -179.8(2) . . . . ? C2A C3A C4A C5A 2.4(3) . . . . ? C3A C4A C5A C6A 2.0(3) . . . . ? C3A C4A C5A C7A -171.4(2) . . . . ? C4A C5A C6A C1A -4.7(3) . . . . ? C7A C5A C6A C1A 169.93(19) . . . . ? C4A C5A C6A N1A 176.55(19) . . . . ? C7A C5A C6A N1A -8.9(2) . . . . ? C2A C1A C6A C5A 2.6(3) . . . . ? C2A C1A C6A N1A -178.8(2) . . . . ? C9A N1A C6A C5A -155.02(19) . . . . ? C8A N1A C6A C5A -4.0(2) . . . . ? C9A N1A C6A C1A 26.3(3) . . . . ? C8A N1A C6A C1A 177.3(2) . . . . ? C6A C5A C7A C21A 142.22(19) . . . . ? C4A C5A C7A C21A -43.8(3) . . . . ? C6A C5A C7A C17A -101.9(2) . . . . ? C4A C5A C7A C17A 72.1(3) . . . . ? C6A C5A C7A C8A 17.1(2) . . . . ? C4A C5A C7A C8A -168.9(2) . . . . ? C9A N1A C8A C18A 43.5(2) . . . . ? C6A N1A C8A C18A -109.72(19) . . . . ? C9A N1A C8A C7A 167.55(17) . . . . ? C6A N1A C8A C7A 14.4(2) . . . . ? C5A C7A C8A N1A -18.4(2) . . . . ? C21A C7A C8A N1A -143.88(17) . . . . ? C17A C7A C8A N1A 101.55(18) . . . . ? C5A C7A C8A C18A 98.9(2) . . . . ? C21A C7A C8A C18A -26.6(2) . . . . ? C17A C7A C8A C18A -141.17(18) . . . . ? C6A N1A C9A O4A -20.9(3) . . . . ? C8A N1A C9A O4A -169.43(19) . . . . ? C6A N1A C9A C10A 160.08(19) . . . . ? C8A N1A C9A C10A 11.5(3) . . . . ? O4A C9A C10A C11A 139.6(2) . . . . ? N1A C9A C10A C11A -41.4(3) . . . . ? C12A O1A C11A C18A -66.5(2) . . . . ? C12A O1A C11A C10A 172.92(19) . . . . ? C9A C10A C11A O1A 135.25(18) . . . . ? C9A C10A C11A C18A 11.6(3) . . . . ? C11A O1A C12A C13A 89.0(3) . . . . ? O1A C12A C13A C14A -64.5(3) . . . . ? C12A C13A C14A C15A 175.8(2) . . . . ? C12A C13A C14A C19A -4.1(4) . . . . ? C13A C14A C15A N2A -128.6(2) . . . . ? C19A C14A C15A N2A 51.3(3) . . . . ? C16A N2A C15A C14A 77.3(2) . . . . ? C21A N2A C15A C14A -45.1(2) . . . . ? C15A N2A C16A C17A -141.72(18) . . . . ? C21A N2A C16A C17A -16.2(2) . . . . ? N2A C16A C17A C7A 36.6(2) . . . . ? C5A C7A C17A C16A -166.64(17) . . . . ? C21A C7A C17A C16A -42.9(2) . . . . ? C8A C7A C17A C16A 79.3(2) . . . . ? O1A C11A C18A C8A -74.9(2) . . . . ? C10A C11A C18A C8A 42.4(2) . . . . ? O1A C11A C18A C19A 54.2(3) . . . . ? C10A C11A C18A C19A 171.45(18) . . . . ? N1A C8A C18A C11A -71.3(2) . . . . ? C7A C8A C18A C11A 172.73(16) . . . . ? N1A C8A C18A C19A 156.53(17) . . . . ? C7A C8A C18A C19A 40.5(2) . . . . ? C13A C14A C19A C20A -179.9(2) . . . . ? C15A C14A C19A C20A 0.1(3) . . . . ? C13A C14A C19A C18A 60.4(3) . . . . ? C15A C14A C19A C18A -119.5(2) . . . . ? C11A C18A C19A C14A -66.3(3) . . . . ? C8A C18A C19A C14A 60.3(3) . . . . ? C11A C18A C19A C20A 172.98(18) . . . . ? C8A C18A C19A C20A -60.4(2) . . . . ? C14A C19A C20A C21A -56.4(2) . . . . ? C18A C19A C20A C21A 67.8(2) . . . . ? C19A C20A C21A N2A 62.3(2) . . . . ? C19A C20A C21A C7A -56.2(2) . . . . ? C15A N2A C21A C20A -9.9(2) . . . . ? C16A N2A C21A C20A -135.22(19) . . . . ? C15A N2A C21A C7A 114.7(2) . . . . ? C16A N2A C21A C7A -10.6(2) . . . . ? C5A C7A C21A C20A -84.0(2) . . . . ? C17A C7A C21A C20A 154.37(18) . . . . ? C8A C7A C21A C20A 34.7(2) . . . . ? C5A C7A C21A N2A 154.26(18) . . . . ? C17A C7A C21A N2A 32.6(2) . . . . ? C8A C7A C21A N2A -87.1(2) . . . . ? C22B O2B C2B C1B -4.0(4) . . . . ? C22B O2B C2B C3B 176.8(2) . . . . ? C6B C1B C2B O2B -178.8(2) . . . . ? C6B C1B C2B C3B 0.4(3) . . . . ? C23B O3B C3B C4B 4.4(3) . . . . ? C23B O3B C3B C2B -177.5(2) . . . . ? O2B C2B C3B O3B -1.3(3) . . . . ? C1B C2B C3B O3B 179.4(2) . . . . ? O2B C2B C3B C4B 176.9(2) . . . . ? C1B C2B C3B C4B -2.4(3) . . . . ? O3B C3B C4B C5B 179.8(2) . . . . ? C2B C3B C4B C5B 1.8(3) . . . . ? C3B C4B C5B C6B 0.8(3) . . . . ? C3B C4B C5B C7B -174.6(2) . . . . ? C4B C5B C6B C1B -2.8(3) . . . . ? C7B C5B C6B C1B 173.4(2) . . . . ? C4B C5B C6B N1B 176.36(19) . . . . ? C7B C5B C6B N1B -7.4(2) . . . . ? C2B C1B C6B C5B 2.2(3) . . . . ? C2B C1B C6B N1B -176.9(2) . . . . ? C9B N1B C6B C5B -155.7(2) . . . . ? C8B N1B C6B C5B -6.5(2) . . . . ? C9B N1B C6B C1B 23.4(4) . . . . ? C8B N1B C6B C1B 172.6(2) . . . . ? C6B C5B C7B C21B 141.99(19) . . . . ? C4B C5B C7B C21B -42.2(3) . . . . ? C6B C5B C7B C17B -101.5(2) . . . . ? C4B C5B C7B C17B 74.3(3) . . . . ? C6B C5B C7B C8B 17.2(2) . . . . ? C4B C5B C7B C8B -167.0(2) . . . . ? C9B N1B C8B C18B 45.2(2) . . . . ? C6B N1B C8B C18B -106.39(19) . . . . ? C9B N1B C8B C7B 168.43(18) . . . . ? C6B N1B C8B C7B 16.9(2) . . . . ? C5B C7B C8B N1B -19.9(2) . . . . ? C21B C7B C8B N1B -145.35(17) . . . . ? C17B C7B C8B N1B 100.81(19) . . . . ? C5B C7B C8B C18B 96.7(2) . . . . ? C21B C7B C8B C18B -28.8(2) . . . . ? C17B C7B C8B C18B -142.61(18) . . . . ? C6B N1B C9B O4B -22.7(3) . . . . ? C8B N1B C9B O4B -169.3(2) . . . . ? C6B N1B C9B C10B 158.1(2) . . . . ? C8B N1B C9B C10B 11.5(3) . . . . ? O4B C9B C10B C11B 135.8(2) . . . . ? N1B C9B C10B C11B -44.9(3) . . . . ? C12B O1B C11B C18B -63.5(2) . . . . ? C12B O1B C11B C10B 175.53(18) . . . . ? C9B C10B C11B O1B 141.21(19) . . . . ? C9B C10B C11B C18B 16.8(3) . . . . ? C11B O1B C12B C13B 89.9(2) . . . . ? O1B C12B C13B C14B -67.3(3) . . . . ? C12B C13B C14B C15B 177.9(2) . . . . ? C12B C13B C14B C19B -3.6(3) . . . . ? C13B C14B C15B N2B -131.5(2) . . . . ? C19B C14B C15B N2B 50.0(3) . . . . ? C16B N2B C15B C14B 78.5(2) . . . . ? C21B N2B C15B C14B -44.6(2) . . . . ? C15B N2B C16B C17B -142.04(18) . . . . ? C21B N2B C16B C17B -15.8(2) . . . . ? N2B C16B C17B C7B 36.8(2) . . . . ? C5B C7B C17B C16B -167.75(18) . . . . ? C21B C7B C17B C16B -43.4(2) . . . . ? C8B C7B C17B C16B 78.3(2) . . . . ? N1B C8B C18B C19B 157.35(18) . . . . ? C7B C8B C18B C19B 41.9(2) . . . . ? N1B C8B C18B C11B -70.6(2) . . . . ? C7B C8B C18B C11B 174.05(17) . . . . ? O1B C11B C18B C8B -78.9(2) . . . . ? C10B C11B C18B C8B 38.5(2) . . . . ? O1B C11B C18B C19B 50.4(3) . . . . ? C10B C11B C18B C19B 167.77(18) . . . . ? C13B C14B C19B C20B -177.4(2) . . . . ? C15B C14B C19B C20B 1.2(3) . . . . ? C13B C14B C19B C18B 63.1(3) . . . . ? C15B C14B C19B C18B -118.3(2) . . . . ? C8B C18B C19B C14B 60.2(2) . . . . ? C11B C18B C19B C14B -66.7(2) . . . . ? C8B C18B C19B C20B -60.5(2) . . . . ? C11B C18B C19B C20B 172.64(17) . . . . ? C14B C19B C20B C21B -56.5(2) . . . . ? C18B C19B C20B C21B 67.1(2) . . . . ? C19B C20B C21B N2B 61.6(2) . . . . ? C19B C20B C21B C7B -56.4(2) . . . . ? C16B N2B C21B C20B -135.69(18) . . . . ? C15B N2B C21B C20B -9.6(2) . . . . ? C16B N2B C21B C7B -11.5(2) . . . . ? C15B N2B C21B C7B 114.57(19) . . . . ? C5B C7B C21B C20B -82.0(2) . . . . ? C17B C7B C21B C20B 155.10(18) . . . . ? C8B C7B C21B C20B 36.2(2) . . . . ? C5B C7B C21B N2B 156.42(17) . . . . ? C17B C7B C21B N2B 33.6(2) . . . . ? C8B C7B C21B N2B -85.3(2) . . . . ? C27 N3 C25 C26 78.9(3) . . . . ? C27 N3 C25 C24 -154.1(2) . . . . ? O6 C24 C25 N3 -0.7(3) . . . . ? O5 C24 C25 N3 176.9(2) . . . . ? O6 C24 C25 C26 126.2(3) . . . . ? O5 C24 C25 C26 -56.2(3) . . . . ? N3 C25 C26 O7 57.7(2) . . . . ? C24 C25 C26 O7 -67.9(2) . . . . ? C25 N3 C27 O8 -2.1(3) . . . . ? C25 N3 C27 C28 179.29(19) . . . . ? O8 C27 C28 C29 4.2(3) . . . . ? N3 C27 C28 C29 -177.2(2) . . . . ? O8 C27 C28 C33 -175.1(2) . . . . ? N3 C27 C28 C33 3.5(3) . . . . ? C33 C28 C29 C30 -0.1(3) . . . . ? C27 C28 C29 C30 -179.5(2) . . . . ? C28 C29 C30 C31 -0.1(3) . . . . ? C29 C30 C31 C32 0.1(4) . . . . ? C29 C30 C31 N4 -179.6(2) . . . . ? O9 N4 C31 C32 165.8(2) . . . . ? O10 N4 C31 C32 -13.2(3) . . . . ? O9 N4 C31 C30 -14.5(3) . . . . ? O10 N4 C31 C30 166.4(2) . . . . ? C30 C31 C32 C33 0.2(4) . . . . ? N4 C31 C32 C33 179.9(2) . . . . ? C31 C32 C33 C28 -0.5(4) . . . . ? C29 C28 C33 C32 0.4(4) . . . . ? C27 C28 C33 C32 179.7(2) . . . . ? C27A N3A C25A C26A 132.9(2) . . . . ? C27A N3A C25A C24A -101.4(2) . . . . ? O6A C24A C25A N3A -146.3(2) . . . . ? O5A C24A C25A N3A 36.1(3) . . . . ? O6A C24A C25A C26A -21.1(3) . . . . ? O5A C24A C25A C26A 161.3(2) . . . . ? N3A C25A C26A O7A -67.3(2) . . . . ? C24A C25A C26A O7A 167.88(19) . . . . ? C25A N3A C27A O8A -3.3(3) . . . . ? C25A N3A C27A C28A 178.60(18) . . . . ? O8A C27A C28A C29A 33.9(3) . . . . ? N3A C27A C28A C29A -147.9(2) . . . . ? O8A C27A C28A C33A -146.4(2) . . . . ? N3A C27A C28A C33A 31.8(3) . . . . ? C33A C28A C29A C30A -1.8(3) . . . . ? C27A C28A C29A C30A 177.9(2) . . . . ? C28A C29A C30A C31A 1.4(3) . . . . ? C29A C30A C31A C32A 1.0(3) . . . . ? C29A C30A C31A N4A -177.9(2) . . . . ? O9A N4A C31A C32A -156.3(2) . . . . ? O10A N4A C31A C32A 22.0(3) . . . . ? O9A N4A C31A C30A 22.7(3) . . . . ? O10A N4A C31A C30A -159.0(2) . . . . ? C30A C31A C32A C33A -3.0(3) . . . . ? N4A C31A C32A C33A 176.03(19) . . . . ? C31A C32A C33A C28A 2.5(3) . . . . ? C29A C28A C33A C32A -0.2(3) . . . . ? C27A C28A C33A C32A -179.91(19) . . . . ? C27B N3B C25B C26B 137.0(2) . . . . ? C27B N3B C25B C24B -98.9(2) . . . . ? O6B C24B C25B N3B -177.7(2) . . . . ? O5B C24B C25B N3B 2.6(3) . . . . ? O6B C24B C25B C26B -53.1(3) . . . . ? O5B C24B C25B C26B 127.3(2) . . . . ? N3B C25B C26B O7B -57.0(3) . . . . ? C24B C25B C26B O7B 177.8(2) . . . . ? C25B N3B C27B O8B -4.3(3) . . . . ? C25B N3B C27B C28B 178.10(18) . . . . ? O8B C27B C28B C29B -15.2(3) . . . . ? N3B C27B C28B C29B 162.5(2) . . . . ? O8B C27B C28B C33B 165.5(2) . . . . ? N3B C27B C28B C33B -16.8(3) . . . . ? C33B C28B C29B C30B 1.9(3) . . . . ? C27B C28B C29B C30B -177.5(2) . . . . ? C28B C29B C30B C31B -0.8(3) . . . . ? C29B C30B C31B C32B -0.8(3) . . . . ? C29B C30B C31B N4B -179.0(2) . . . . ? O10B N4B C31B C30B 166.6(2) . . . . ? O9B N4B C31B C30B -12.3(3) . . . . ? O10B N4B C31B C32B -11.7(3) . . . . ? O9B N4B C31B C32B 169.4(2) . . . . ? C30B C31B C32B C33B 1.3(4) . . . . ? N4B C31B C32B C33B 179.5(2) . . . . ? C31B C32B C33B C28B -0.3(4) . . . . ? C29B C28B C33B C32B -1.3(4) . . . . ? C27B C28B C33B C32B 178.0(2) . . . . ? 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 2.613(3) 162.6 . N2A H2A O5A 0.93 1.74 2.620(3) 157.4 . N2B H2B O5B 0.93 1.75 2.638(3) 157.8 . O7 H7 O1W 1.01 1.71 2.711(3) 169.0 . N3 H3 O37A 0.88 2.36 3.226(5) 166.2 2_746 O7A H7A O51W 0.89 1.94 2.781(9) 156.8 . O7A H7A O5W 0.89 2.02 2.871(7) 159.7 . O7A H7A O38B 0.89 2.40 2.872(18) 113.6 . N3A H3A O8 0.88 2.08 2.813(3) 140.4 2_746 O7B H7B O2W 0.82 2.09 2.899(3) 167.2 1_455 N3B H3B O3W 0.88 2.06 2.901(3) 158.6 2_645 O1W H11W O8A 0.88 1.94 2.803(2) 166.3 . O1W H12W O34 0.88 1.88 2.748(3) 167.6 2_756 O2W H21W O5B 0.88 2.05 2.881(3) 157.0 2_655 O2W H22W O37A 0.88 1.89 2.665(5) 145.0 . O2W H22W O37 0.88 2.01 2.819(4) 151.6 . O3W H31W O8B 0.88 1.92 2.797(3) 179.2 1_655 O3W H32W O38 0.88 1.95 2.711(4) 143.7 . O3W H32W O38A 0.88 2.08 2.946(7) 170.7 . O4W H41W O36 0.88 1.91 2.772(4) 165.4 . O4W H42W O2B 0.88 1.90 2.776(3) 179.3 . O5W H51W O6 0.85 1.92 2.765(6) 178.1 2_756 O5W H52W O2W 0.85 2.00 2.767(7) 150.1 . O51W H53W O7A 0.85 2.19 2.781(9) 127.0 . O51W H54W O38A 0.94 2.19 2.773(10) 119.1 . O34 H34 O5A 0.83 1.90 2.714(3) 166.4 . O35 H35 O7 0.86 1.90 2.741(3) 166.9 . O36 H36 O6A 0.97 1.79 2.738(3) 162.9 . O37 H37 O4W 0.79 2.00 2.754(4) 160.0 . O37A H371 O6 0.89 1.72 2.606(5) 179.5 2_756 O38 H38 O5W 0.94 1.95 2.822(7) 153.9 . O38A H381 O51W 0.61 2.24 2.773(10) 148.1 . O38B H382 O6B 0.81 1.91 2.725(19) 178.3 1_655 _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 35.00 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 0.615 _refine_diff_density_min -0.618 _refine_diff_density_rms 0.064 # start Validation Reply Form _vrf_PLAT417_3 ; PROBLEM: Short Inter D-H..H-D H7A .. H53W .. 1.31 Ang. RESPONSE: Disordered water molecule ; _vrf_PLAT432_3 ; PROBLEM: Short Inter X...Y Contact C38 .. O38B .. 2.39 Ang. RESPONSE: disordered methanol molecule ; _vrf_PLAT770_3 ; PROBLEM: Suspect C-H Bond in CIF: C38 -- H381 .. 1.48 Ang. RESPONSE: disordered methanol molecule ; _vrf_PLAT772_3 ; PROBLEM: Suspect O-H Bond in CIF: O5W -- H54W .. 1.43 Ang. RESPONSE: disordered water molecule ; # end Validation Reply Form #===== end data_4 _database_code_depnum_ccdc_archive 'CCDC 758145' #TrackingRef 'bialonska1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; brucinium N-(4-nitrobenzoyl)-(D~0.85~L~0.15~)-serinate methanol disolvate ; _chemical_name_common ;brucinium N-(4-nitrobenzoyl)-(D!0.85$L!0.15$)-serinate methanol disolvate ; _chemical_melting_point ? _chemical_formula_moiety 'C23 H27 N2 O4, C10 H9 N2 O6, 2(C H4 O)' _chemical_formula_sum 'C35 H44 N4 O12' _chemical_formula_weight 712.74 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 7.745(2) _cell_length_b 12.322(2) _cell_length_c 35.716(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3408.5(11) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 8212 _cell_measurement_theta_min 3.11 _cell_measurement_theta_max 36.63 _exptl_crystal_description block _exptl_crystal_colour pale-yellow _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.40 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.389 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1512 _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 25685 _diffrn_reflns_av_R_equivalents 0.0555 _diffrn_reflns_av_sigmaI/netI 0.0404 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -46 _diffrn_reflns_limit_l_max 45 _diffrn_reflns_theta_min 3.11 _diffrn_reflns_theta_max 28.00 _reflns_number_total 4602 _reflns_number_gt 3735 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET) (compiled May 8 2007,13:10:02) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET) (compiled May 8 2007,13:10:02) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET) (compiled May 8 2007,13:10:02) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0563P)^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 4602 _refine_ls_number_parameters 465 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0515 _refine_ls_R_factor_gt 0.0382 _refine_ls_wR_factor_ref 0.0906 _refine_ls_wR_factor_gt 0.0868 _refine_ls_goodness_of_fit_ref 0.984 _refine_ls_restrained_S_all 0.984 _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 0.2612(2) 0.71899(11) 0.81476(4) 0.0202(3) Uani 1 1 d . . . O2 O 0.3101(2) 0.13725(11) 0.67869(4) 0.0211(3) Uani 1 1 d . . . O3 O 0.2552(2) 0.02132(11) 0.73803(4) 0.0220(4) Uani 1 1 d . . . O4 O 0.2791(2) 0.53290(12) 0.70075(5) 0.0274(4) Uani 1 1 d . . . N1 N 0.3351(2) 0.46429(13) 0.75863(5) 0.0165(4) Uani 1 1 d . . . N2 N 0.3130(3) 0.37295(14) 0.88424(5) 0.0208(4) Uani 1 1 d . . . H2 H 0.3147 0.3151 0.9010 0.025 Uiso 1 1 calc R . . C1 C 0.3276(3) 0.30543(16) 0.71399(6) 0.0169(4) Uani 1 1 d . . . H1 H 0.3425 0.3485 0.6922 0.020 Uiso 1 1 calc R . . C2 C 0.3084(3) 0.19352(16) 0.71178(6) 0.0179(5) Uani 1 1 d . . . C3 C 0.2828(3) 0.13023(16) 0.74442(6) 0.0174(5) Uani 1 1 d . . . C4 C 0.2858(3) 0.17889(16) 0.77935(6) 0.0183(5) Uani 1 1 d . . . H4 H 0.2728 0.1365 0.8014 0.022 Uiso 1 1 calc R . . C5 C 0.3081(3) 0.29123(16) 0.78179(6) 0.0174(5) Uani 1 1 d . . . C6 C 0.3242(3) 0.35183(16) 0.74956(6) 0.0167(4) Uani 1 1 d . . . C7 C 0.3331(3) 0.36067(15) 0.81632(6) 0.0163(4) Uani 1 1 d . . . C8 C 0.3145(3) 0.47842(16) 0.79979(6) 0.0169(4) Uani 1 1 d . . . H8 H 0.4087 0.5259 0.8097 0.020 Uiso 1 1 calc R . . C9 C 0.2866(3) 0.54566(17) 0.73513(6) 0.0199(5) Uani 1 1 d . . . C10 C 0.2434(3) 0.65380(16) 0.75283(6) 0.0208(5) Uani 1 1 d . . . H10A H 0.1666 0.6937 0.7355 0.025 Uiso 1 1 calc R . . H10B H 0.3517 0.6961 0.7550 0.025 Uiso 1 1 calc R . . C11 C 0.1565(3) 0.65134(16) 0.79165(6) 0.0191(5) Uani 1 1 d . . . H11 H 0.0386 0.6840 0.7896 0.023 Uiso 1 1 calc R . . C12 C 0.1890(3) 0.74243(17) 0.85115(7) 0.0234(5) Uani 1 1 d . . . H12A H 0.0618 0.7481 0.8490 0.028 Uiso 1 1 calc R . . H12B H 0.2336 0.8131 0.8601 0.028 Uiso 1 1 calc R . . C13 C 0.2340(3) 0.65552(17) 0.87907(6) 0.0216(5) Uani 1 1 d . . . H13 H 0.3042 0.6745 0.8999 0.026 Uiso 1 1 calc R . . C14 C 0.1805(3) 0.55374(17) 0.87609(6) 0.0209(5) Uani 1 1 d . . . C15 C 0.2330(3) 0.46860(17) 0.90418(7) 0.0240(5) Uani 1 1 d . . . H15A H 0.1305 0.4444 0.9185 0.029 Uiso 1 1 calc R . . H15B H 0.3172 0.4998 0.9221 0.029 Uiso 1 1 calc R . . C16 C 0.4970(3) 0.39436(18) 0.87240(7) 0.0235(5) Uani 1 1 d . . . H16A H 0.5792 0.3605 0.8901 0.028 Uiso 1 1 calc R . . H16B H 0.5202 0.4733 0.8713 0.028 Uiso 1 1 calc R . . C17 C 0.5132(3) 0.34385(17) 0.83390(7) 0.0200(5) Uani 1 1 d . . . H17A H 0.5416 0.2657 0.8357 0.024 Uiso 1 1 calc R . . H17B H 0.6036 0.3807 0.8190 0.024 Uiso 1 1 calc R . . C18 C 0.1397(3) 0.53353(16) 0.80535(6) 0.0173(5) Uani 1 1 d . . . H18 H 0.0588 0.4972 0.7875 0.021 Uiso 1 1 calc R . . C19 C 0.0639(3) 0.51418(17) 0.84468(7) 0.0196(5) Uani 1 1 d . . . H19 H -0.0505 0.5514 0.8466 0.024 Uiso 1 1 calc R . . C20 C 0.0375(3) 0.39064(17) 0.84835(7) 0.0211(5) Uani 1 1 d . . . H20A H -0.0276 0.3742 0.8715 0.025 Uiso 1 1 calc R . . H20B H -0.0296 0.3632 0.8267 0.025 Uiso 1 1 calc R . . C21 C 0.2125(3) 0.33619(16) 0.84958(6) 0.0184(5) Uani 1 1 d . . . H21 H 0.1948 0.2559 0.8511 0.022 Uiso 1 1 calc R . . C22 C 0.3344(3) 0.20061(18) 0.64536(6) 0.0239(5) Uani 1 1 d . . . H22A H 0.3340 0.1527 0.6235 0.036 Uiso 1 1 calc R . . H22B H 0.4451 0.2389 0.6468 0.036 Uiso 1 1 calc R . . H22C H 0.2405 0.2535 0.6431 0.036 Uiso 1 1 calc R . . C23 C 0.2312(4) -0.04477(17) 0.77068(7) 0.0278(6) Uani 1 1 d . . . H23A H 0.2128 -0.1203 0.7631 0.042 Uiso 1 1 calc R . . H23B H 0.1304 -0.0189 0.7847 0.042 Uiso 1 1 calc R . . H23C H 0.3341 -0.0402 0.7866 0.042 Uiso 1 1 calc R . . O5 O 0.2795(2) 0.21896(12) 0.93405(4) 0.0263(4) Uani 1 1 d . . . O6 O 0.4118(3) 0.33860(13) 0.97100(5) 0.0363(5) Uani 1 1 d . . . O7 O 0.3472(3) 0.13197(14) 1.06375(5) 0.0349(4) Uani 1 1 d . . . H7 H 0.2915 0.0767 1.0564 0.052 Uiso 1 1 d . . . O8 O 0.3769(2) -0.03557(14) 0.96353(5) 0.0303(4) Uani 1 1 d . C . O9 O -0.2787(3) -0.40245(12) 0.94173(5) 0.0319(4) Uani 1 1 d . . . O10 O -0.4687(2) -0.27702(15) 0.95059(6) 0.0357(5) Uani 1 1 d . . . C25 C 0.3423(4) 0.16512(18) 0.99678(7) 0.0297(6) Uani 1 1 d . . . H25 H 0.4502 0.1201 0.9956 0.036 Uiso 0.85 1 d P A 1 H25A H 0.2388 0.2059 1.0055 0.036 Uiso 0.15 1 d P B 2 N3 N 0.2037(3) 0.08554(14) 0.99229(5) 0.0244(5) Uani 1 1 d . C . H3 H 0.1003 0.0995 1.0013 0.029 Uiso 1 1 calc R . . N4 N -0.3192(3) -0.30870(15) 0.94924(5) 0.0259(5) Uani 1 1 d . C . C24 C 0.3419(3) 0.24907(16) 0.96469(7) 0.0210(5) Uani 1 1 d . C . C26 C 0.3371(4) 0.2139(2) 1.03517(8) 0.0219(6) Uani 0.85 1 d P C 1 H26A H 0.4348 0.2651 1.0381 0.026 Uiso 0.85 1 calc PR C 1 H26B H 0.2285 0.2555 1.0382 0.026 Uiso 0.85 1 calc PR C 1 C26A C 0.426(2) 0.1613(14) 1.0276(5) 0.028(4) Uiso 0.15 1 d P C 2 H26C H 0.4780 0.2339 1.0310 0.033 Uiso 0.15 1 calc PR C 2 H26D H 0.5223 0.1101 1.0236 0.033 Uiso 0.15 1 calc PR C 2 C27 C 0.2332(3) -0.00788(17) 0.97465(6) 0.0221(5) Uani 1 1 d . . . C28 C 0.0810(3) -0.08271(17) 0.96912(6) 0.0193(5) Uani 1 1 d . C . C29 C 0.1189(3) -0.18907(18) 0.95898(7) 0.0237(5) Uani 1 1 d . . . H29 H 0.2360 -0.2106 0.9560 0.028 Uiso 1 1 calc R C . C30 C -0.0119(3) -0.26436(18) 0.95306(7) 0.0238(5) Uani 1 1 d . C . H30 H 0.0141 -0.3373 0.9466 0.029 Uiso 1 1 calc R . . C31 C -0.1804(3) -0.23014(17) 0.95689(6) 0.0213(5) Uani 1 1 d . . . C32 C -0.2243(3) -0.12516(17) 0.96708(7) 0.0235(5) Uani 1 1 d . C . H32 H -0.3417 -0.1041 0.9696 0.028 Uiso 1 1 calc R . . C33 C -0.0917(3) -0.05157(18) 0.97345(7) 0.0242(5) Uani 1 1 d . . . H33 H -0.1185 0.0206 0.9808 0.029 Uiso 1 1 calc R C . O34 O 0.4817(3) -0.08178(16) 0.89040(6) 0.0458(5) Uani 1 1 d . . . H34 H 0.4383 -0.0764 0.9167 0.069 Uiso 1 1 d . . . C34 C 0.4470(5) 0.0197(2) 0.87406(9) 0.0469(8) Uani 1 1 d . . . H34A H 0.3218 0.0302 0.8723 0.070 Uiso 1 1 calc R . . H34B H 0.4979 0.0225 0.8490 0.070 Uiso 1 1 calc R . . H34C H 0.4970 0.0773 0.8896 0.070 Uiso 1 1 calc R . . O35 O 0.0185(3) 0.61064(19) 0.65351(6) 0.0536(6) Uani 1 1 d . . . H35 H 0.1071 0.5833 0.6682 0.080 Uiso 1 1 d . . . C35 C 0.0581(5) 0.5806(4) 0.61661(9) 0.0702(12) Uani 1 1 d . . . H35A H -0.0474 0.5814 0.6015 0.105 Uiso 1 1 calc R . . H35B H 0.1076 0.5074 0.6165 0.105 Uiso 1 1 calc R . . H35C H 0.1417 0.6320 0.6061 0.105 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0211(8) 0.0196(7) 0.0199(8) -0.0020(6) -0.0003(7) -0.0009(6) O2 0.0296(9) 0.0200(7) 0.0136(8) -0.0024(6) -0.0014(7) -0.0023(7) O3 0.0295(9) 0.0150(7) 0.0215(9) -0.0007(6) -0.0020(7) -0.0004(7) O4 0.0422(11) 0.0243(7) 0.0158(9) 0.0022(7) -0.0009(8) 0.0038(8) N1 0.0205(10) 0.0150(8) 0.0140(10) -0.0008(7) -0.0009(8) 0.0002(7) N2 0.0280(11) 0.0197(8) 0.0148(10) 0.0016(7) -0.0017(8) -0.0005(8) C1 0.0160(11) 0.0194(9) 0.0152(12) 0.0033(8) 0.0004(9) 0.0001(8) C2 0.0169(11) 0.0208(10) 0.0161(12) -0.0033(8) -0.0012(9) -0.0012(8) C3 0.0172(11) 0.0142(9) 0.0208(12) -0.0006(8) -0.0004(9) -0.0004(8) C4 0.0215(12) 0.0176(10) 0.0159(12) 0.0023(8) -0.0006(9) -0.0004(8) C5 0.0169(11) 0.0175(9) 0.0176(12) -0.0021(8) -0.0021(9) 0.0008(8) C6 0.0156(11) 0.0151(9) 0.0193(12) -0.0012(8) -0.0008(9) 0.0011(8) C7 0.0195(11) 0.0136(9) 0.0158(12) -0.0002(8) -0.0028(9) 0.0007(8) C8 0.0203(12) 0.0171(9) 0.0135(11) 0.0012(8) -0.0006(9) 0.0002(8) C9 0.0195(12) 0.0198(10) 0.0205(13) 0.0017(9) 0.0000(10) -0.0004(9) C10 0.0257(12) 0.0154(9) 0.0212(13) 0.0018(8) -0.0018(10) -0.0008(9) C11 0.0194(11) 0.0160(9) 0.0219(13) 0.0002(9) -0.0020(10) 0.0006(9) C12 0.0280(13) 0.0198(10) 0.0224(13) -0.0044(9) 0.0018(10) 0.0022(9) C13 0.0235(12) 0.0261(10) 0.0152(12) -0.0044(9) 0.0039(10) 0.0014(10) C14 0.0225(12) 0.0244(10) 0.0158(12) -0.0033(9) 0.0049(10) 0.0021(9) C15 0.0329(14) 0.0199(10) 0.0192(12) -0.0016(9) 0.0026(10) -0.0007(10) C16 0.0249(13) 0.0215(10) 0.0240(14) 0.0017(10) -0.0047(11) -0.0002(9) C17 0.0216(12) 0.0190(10) 0.0194(13) 0.0023(9) -0.0019(9) 0.0022(9) C18 0.0185(11) 0.0160(9) 0.0174(12) -0.0006(8) -0.0007(9) -0.0004(8) C19 0.0168(11) 0.0210(10) 0.0212(13) 0.0010(9) 0.0010(9) 0.0000(8) C20 0.0216(12) 0.0217(10) 0.0202(13) 0.0006(9) 0.0033(10) -0.0042(9) C21 0.0259(12) 0.0179(9) 0.0114(11) 0.0003(8) -0.0013(9) -0.0025(9) C22 0.0316(14) 0.0243(11) 0.0158(12) -0.0022(9) 0.0003(11) -0.0019(10) C23 0.0420(16) 0.0169(10) 0.0246(13) 0.0025(9) 0.0019(12) -0.0015(10) O5 0.0415(11) 0.0213(7) 0.0161(9) 0.0011(6) -0.0066(8) -0.0050(7) O6 0.0584(13) 0.0221(8) 0.0284(11) 0.0049(8) -0.0120(10) -0.0114(8) O7 0.0417(11) 0.0393(9) 0.0236(10) 0.0065(8) -0.0076(9) -0.0128(8) O8 0.0238(10) 0.0366(9) 0.0304(10) -0.0025(8) 0.0009(8) -0.0018(8) O9 0.0487(12) 0.0185(7) 0.0283(10) 0.0013(7) -0.0056(9) -0.0060(8) O10 0.0274(10) 0.0364(10) 0.0432(13) 0.0007(9) -0.0070(9) -0.0029(8) C25 0.0406(16) 0.0265(11) 0.0220(14) 0.0043(10) -0.0064(12) -0.0100(12) N3 0.0321(12) 0.0205(8) 0.0207(11) 0.0007(8) -0.0009(9) -0.0026(8) N4 0.0329(13) 0.0259(10) 0.0189(11) 0.0043(8) -0.0034(9) -0.0045(9) C24 0.0265(12) 0.0177(9) 0.0189(13) 0.0000(9) -0.0015(10) -0.0002(9) C26 0.0263(15) 0.0232(12) 0.0163(14) 0.0023(11) -0.0029(12) -0.0034(12) C27 0.0313(14) 0.0215(10) 0.0135(12) 0.0022(9) -0.0021(10) -0.0011(9) C28 0.0249(12) 0.0200(10) 0.0129(12) 0.0011(9) 0.0021(9) 0.0002(9) C29 0.0222(13) 0.0241(11) 0.0247(14) -0.0029(10) 0.0037(10) 0.0030(9) C30 0.0294(14) 0.0195(10) 0.0226(14) -0.0047(9) 0.0029(11) 0.0001(9) C31 0.0276(13) 0.0207(10) 0.0157(12) 0.0024(9) -0.0032(10) -0.0026(9) C32 0.0233(12) 0.0234(10) 0.0237(13) -0.0002(9) -0.0004(10) 0.0058(9) C33 0.0291(13) 0.0191(10) 0.0243(14) 0.0002(10) -0.0002(11) 0.0038(9) O34 0.0562(14) 0.0418(11) 0.0393(13) -0.0073(9) 0.0026(11) 0.0070(10) C34 0.059(2) 0.0475(17) 0.0342(18) 0.0035(14) 0.0083(15) 0.0041(16) O35 0.0569(15) 0.0728(14) 0.0311(12) -0.0015(11) -0.0014(11) 0.0348(12) C35 0.068(3) 0.115(3) 0.0278(19) 0.000(2) 0.0002(17) 0.043(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C11 1.426(3) . ? O1 C12 1.444(3) . ? O2 C2 1.370(3) . ? O2 C22 1.436(3) . ? O3 C3 1.378(2) . ? O3 C23 1.434(3) . ? O4 C9 1.239(3) . ? N1 C9 1.360(3) . ? N1 C6 1.426(3) . ? N1 C8 1.489(3) . ? N2 C16 1.510(3) . ? N2 C15 1.510(3) . ? N2 C21 1.531(3) . ? N2 H2 0.9300 . ? C1 C2 1.389(3) . ? C1 C6 1.393(3) . ? C1 H1 0.9500 . ? C2 C3 1.416(3) . ? C3 C4 1.384(3) . ? C4 C5 1.398(3) . ? C4 H4 0.9500 . ? C5 C6 1.378(3) . ? C5 C7 1.513(3) . ? C7 C21 1.541(3) . ? C7 C17 1.544(3) . ? C7 C8 1.573(3) . ? C8 C18 1.528(3) . ? C8 H8 1.0000 . ? C9 C10 1.512(3) . ? C10 C11 1.542(3) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C18 1.537(3) . ? C11 H11 1.0000 . ? C12 C13 1.504(3) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.325(3) . ? C13 H13 0.9500 . ? C14 C15 1.507(3) . ? C14 C19 1.520(3) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 C17 1.515(3) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 C19 1.541(3) . ? C18 H18 1.0000 . ? C19 C20 1.542(3) . ? C19 H19 1.0000 . ? C20 C21 1.513(3) . ? 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 1.253(3) . ? O6 C24 1.249(3) . ? O7 C26 1.438(3) . ? O7 C26A 1.473(18) . ? O7 H7 0.8477 . ? O8 C27 1.230(3) . ? O9 N4 1.227(3) . ? O10 N4 1.223(3) . ? C25 C26A 1.275(18) . ? C25 N3 1.463(3) . ? C25 C26 1.498(4) . ? C25 C24 1.544(3) . ? C25 H25 1.0036 . ? C25 H25A 0.9968 . ? N3 C27 1.332(3) . ? N3 H3 0.8800 . ? N4 C31 1.472(3) . ? C26 H25A 1.3073 . ? C26 H26A 0.9900 . ? C26 H26B 0.9900 . ? C26A H25 1.2634 . ? C26A H26C 0.9900 . ? C26A H26D 0.9900 . ? C27 C28 1.510(3) . ? C28 C29 1.391(3) . ? C28 C33 1.400(4) . ? C29 C30 1.390(3) . ? C29 H29 0.9500 . ? C30 C31 1.379(3) . ? C30 H30 0.9500 . ? C31 C32 1.386(3) . ? C32 C33 1.389(3) . ? C32 H32 0.9500 . ? C33 H33 0.9500 . ? O34 C34 1.406(4) . ? O34 H34 0.9997 . ? C34 H34A 0.9800 . ? C34 H34B 0.9800 . ? C34 H34C 0.9800 . ? O35 C35 1.403(4) . ? O35 H35 0.9273 . ? C35 H35A 0.9800 . ? C35 H35B 0.9800 . ? C35 H35C 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 114.66(18) . . ? C2 O2 C22 116.17(15) . . ? C3 O3 C23 116.00(17) . . ? C9 N1 C6 124.03(18) . . ? C9 N1 C8 119.56(17) . . ? C6 N1 C8 109.38(16) . . ? C16 N2 C15 112.52(18) . . ? C16 N2 C21 107.79(18) . . ? C15 N2 C21 113.79(18) . . ? C16 N2 H2 107.5 . . ? C15 N2 H2 107.5 . . ? C21 N2 H2 107.5 . . ? C2 C1 C6 117.2(2) . . ? C2 C1 H1 121.4 . . ? C6 C1 H1 121.4 . . ? O2 C2 C1 123.4(2) . . ? O2 C2 C3 115.62(17) . . ? C1 C2 C3 121.0(2) . . ? O3 C3 C4 125.0(2) . . ? O3 C3 C2 114.94(19) . . ? C4 C3 C2 120.06(19) . . ? C3 C4 C5 119.2(2) . . ? C3 C4 H4 120.4 . . ? C5 C4 H4 120.4 . . ? C6 C5 C4 119.7(2) . . ? C6 C5 C7 111.28(18) . . ? C4 C5 C7 128.8(2) . . ? C5 C6 C1 122.77(19) . . ? C5 C6 N1 110.00(18) . . ? C1 C6 N1 127.23(19) . . ? C5 C7 C21 116.08(18) . . ? C5 C7 C17 111.80(18) . . ? C21 C7 C17 102.01(17) . . ? C5 C7 C8 101.77(17) . . ? C21 C7 C8 114.46(17) . . ? C17 C7 C8 111.06(18) . . ? N1 C8 C18 105.98(17) . . ? N1 C8 C7 104.64(15) . . ? C18 C8 C7 116.26(18) . . ? N1 C8 H8 109.9 . . ? C18 C8 H8 109.9 . . ? C7 C8 H8 109.9 . . ? O4 C9 N1 122.05(19) . . ? O4 C9 C10 121.04(19) . . ? N1 C9 C10 116.90(19) . . ? C9 C10 C11 117.07(17) . . ? C9 C10 H10A 108.0 . . ? C11 C10 H10A 108.0 . . ? C9 C10 H10B 108.0 . . ? C11 C10 H10B 108.0 . . ? H10A C10 H10B 107.3 . . ? O1 C11 C18 114.55(18) . . ? O1 C11 C10 105.10(18) . . ? C18 C11 C10 109.98(17) . . ? O1 C11 H11 109.0 . . ? C18 C11 H11 109.0 . . ? C10 C11 H11 109.0 . . ? O1 C12 C13 111.37(17) . . ? 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 123.2(2) . . ? C14 C13 H13 118.4 . . ? C12 C13 H13 118.4 . . ? C13 C14 C15 121.4(2) . . ? C13 C14 C19 123.3(2) . . ? C15 C14 C19 115.35(18) . . ? C14 C15 N2 109.88(18) . . ? 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 105.10(19) . . ? 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 103.85(18) . . ? C16 C17 H17A 111.0 . . ? C7 C17 H17A 111.0 . . ? C16 C17 H17B 111.0 . . ? C7 C17 H17B 111.0 . . ? H17A C17 H17B 109.0 . . ? C8 C18 C11 107.67(18) . . ? C8 C18 C19 112.80(18) . . ? C11 C18 C19 117.93(17) . . ? C8 C18 H18 105.8 . . ? C11 C18 H18 105.8 . . ? C19 C18 H18 105.8 . . ? C14 C19 C18 113.37(19) . . ? C14 C19 C20 109.44(19) . . ? C18 C19 C20 106.31(18) . . ? C14 C19 H19 109.2 . . ? C18 C19 H19 109.2 . . ? C20 C19 H19 109.2 . . ? C21 C20 C19 108.75(18) . . ? 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 N2 110.37(18) . . ? C20 C21 C7 115.72(18) . . ? N2 C21 C7 104.88(18) . . ? 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 . . ? C26 O7 C26A 39.4(7) . . ? C26 O7 H7 108.5 . . ? C26A O7 H7 97.8 . . ? C26A C25 N3 116.2(8) . . ? C26A C25 C26 40.5(8) . . ? N3 C25 C26 110.5(2) . . ? C26A C25 C24 131.7(8) . . ? N3 C25 C24 111.5(2) . . ? C26 C25 C24 114.2(2) . . ? C26A C25 H25 66.1 . . ? N3 C25 H25 103.6 . . ? C26 C25 H25 106.4 . . ? C24 C25 H25 110.0 . . ? C26A C25 H25A 98.9 . . ? N3 C25 H25A 77.4 . . ? C26 C25 H25A 59.2 . . ? C24 C25 H25A 83.9 . . ? H25 C25 H25A 164.0 . . ? C27 N3 C25 120.3(2) . . ? C27 N3 H3 119.8 . . ? C25 N3 H3 119.8 . . ? O10 N4 O9 123.5(2) . . ? O10 N4 C31 118.30(19) . . ? O9 N4 C31 118.2(2) . . ? O6 C24 O5 125.9(2) . . ? O6 C24 C25 117.2(2) . . ? O5 C24 C25 116.80(19) . . ? O7 C26 C25 111.5(2) . . ? O7 C26 H25A 123.6 . . ? C25 C26 H25A 40.9 . . ? O7 C26 H26A 109.3 . . ? C25 C26 H26A 109.3 . . ? H25A C26 H26A 125.3 . . ? O7 C26 H26B 109.3 . . ? C25 C26 H26B 109.3 . . ? H25A C26 H26B 68.5 . . ? H26A C26 H26B 108.0 . . ? C25 C26A O7 123.9(13) . . ? C25 C26A H25 46.6 . . ? O7 C26A H25 139.1 . . ? C25 C26A H26C 106.4 . . ? O7 C26A H26C 106.4 . . ? H25 C26A H26C 114.4 . . ? C25 C26A H26D 106.4 . . ? O7 C26A H26D 106.4 . . ? H25 C26A H26D 60.0 . . ? H26C C26A H26D 106.4 . . ? O8 C27 N3 123.2(2) . . ? O8 C27 C28 119.68(19) . . ? N3 C27 C28 117.1(2) . . ? C29 C28 C33 119.3(2) . . ? C29 C28 C27 116.4(2) . . ? C33 C28 C27 124.4(2) . . ? C30 C29 C28 121.0(2) . . ? C30 C29 H29 119.5 . . ? C28 C29 H29 119.5 . . ? C31 C30 C29 118.1(2) . . ? C31 C30 H30 121.0 . . ? C29 C30 H30 121.0 . . ? C30 C31 C32 122.9(2) . . ? C30 C31 N4 118.1(2) . . ? C32 C31 N4 118.9(2) . . ? C31 C32 C33 118.1(2) . . ? C31 C32 H32 120.9 . . ? C33 C32 H32 120.9 . . ? C32 C33 C28 120.6(2) . . ? C32 C33 H33 119.7 . . ? C28 C33 H33 119.7 . . ? C34 O34 H34 105.5 . . ? O34 C34 H34A 109.5 . . ? O34 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? O34 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? C35 O35 H35 105.9 . . ? 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 . . ? 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 0.3(3) . . . . ? C22 O2 C2 C3 179.4(2) . . . . ? C6 C1 C2 O2 -179.6(2) . . . . ? C6 C1 C2 C3 1.3(3) . . . . ? C23 O3 C3 C4 -1.1(3) . . . . ? C23 O3 C3 C2 179.2(2) . . . . ? O2 C2 C3 O3 -2.9(3) . . . . ? C1 C2 C3 O3 176.3(2) . . . . ? O2 C2 C3 C4 177.4(2) . . . . ? C1 C2 C3 C4 -3.4(3) . . . . ? O3 C3 C4 C5 -177.4(2) . . . . ? C2 C3 C4 C5 2.2(3) . . . . ? C3 C4 C5 C6 1.0(3) . . . . ? C3 C4 C5 C7 -173.4(2) . . . . ? C4 C5 C6 C1 -3.2(3) . . . . ? C7 C5 C6 C1 172.1(2) . . . . ? C4 C5 C6 N1 176.5(2) . . . . ? C7 C5 C6 N1 -8.2(3) . . . . ? C2 C1 C6 C5 2.0(3) . . . . ? C2 C1 C6 N1 -177.6(2) . . . . ? C9 N1 C6 C5 -153.8(2) . . . . ? C8 N1 C6 C5 -3.5(2) . . . . ? C9 N1 C6 C1 25.9(4) . . . . ? C8 N1 C6 C1 176.2(2) . . . . ? C6 C5 C7 C21 140.44(19) . . . . ? C4 C5 C7 C21 -44.8(3) . . . . ? C6 C5 C7 C17 -103.1(2) . . . . ? C4 C5 C7 C17 71.6(3) . . . . ? C6 C5 C7 C8 15.5(2) . . . . ? C4 C5 C7 C8 -169.8(2) . . . . ? C9 N1 C8 C18 41.3(2) . . . . ? C6 N1 C8 C18 -110.50(18) . . . . ? C9 N1 C8 C7 164.73(19) . . . . ? C6 N1 C8 C7 12.9(2) . . . . ? C5 C7 C8 N1 -16.4(2) . . . . ? C21 C7 C8 N1 -142.46(18) . . . . ? C17 C7 C8 N1 102.7(2) . . . . ? C5 C7 C8 C18 100.1(2) . . . . ? C21 C7 C8 C18 -26.0(3) . . . . ? C17 C7 C8 C18 -140.81(19) . . . . ? C6 N1 C9 O4 -22.6(4) . . . . ? C8 N1 C9 O4 -170.1(2) . . . . ? C6 N1 C9 C10 158.0(2) . . . . ? C8 N1 C9 C10 10.5(3) . . . . ? O4 C9 C10 C11 146.1(2) . . . . ? N1 C9 C10 C11 -34.5(3) . . . . ? C12 O1 C11 C18 -68.4(2) . . . . ? C12 O1 C11 C10 170.73(17) . . . . ? C9 C10 C11 O1 126.6(2) . . . . ? C9 C10 C11 C18 2.8(3) . . . . ? C11 O1 C12 C13 86.4(2) . . . . ? O1 C12 C13 C14 -64.1(3) . . . . ? C12 C13 C14 C15 178.2(2) . . . . ? C12 C13 C14 C19 -1.7(4) . . . . ? C13 C14 C15 N2 -126.0(2) . . . . ? C19 C14 C15 N2 54.0(3) . . . . ? C16 N2 C15 C14 77.8(2) . . . . ? C21 N2 C15 C14 -45.2(3) . . . . ? C15 N2 C16 C17 -139.99(18) . . . . ? C21 N2 C16 C17 -13.7(2) . . . . ? N2 C16 C17 C7 33.9(2) . . . . ? C5 C7 C17 C16 -165.45(18) . . . . ? C21 C7 C17 C16 -40.8(2) . . . . ? C8 C7 C17 C16 81.6(2) . . . . ? N1 C8 C18 C11 -71.1(2) . . . . ? C7 C8 C18 C11 173.13(18) . . . . ? N1 C8 C18 C19 157.04(17) . . . . ? C7 C8 C18 C19 41.3(2) . . . . ? O1 C11 C18 C8 -70.1(2) . . . . ? C10 C11 C18 C8 48.0(2) . . . . ? O1 C11 C18 C19 58.9(3) . . . . ? C10 C11 C18 C19 176.99(19) . . . . ? C13 C14 C19 C18 57.7(3) . . . . ? C15 C14 C19 C18 -122.2(2) . . . . ? C13 C14 C19 C20 176.2(2) . . . . ? C15 C14 C19 C20 -3.7(3) . . . . ? C8 C18 C19 C14 58.5(2) . . . . ? C11 C18 C19 C14 -68.0(3) . . . . ? C8 C18 C19 C20 -61.7(2) . . . . ? C11 C18 C19 C20 171.7(2) . . . . ? C14 C19 C20 C21 -54.5(2) . . . . ? C18 C19 C20 C21 68.3(2) . . . . ? C19 C20 C21 N2 63.0(2) . . . . ? C19 C20 C21 C7 -55.9(3) . . . . ? C16 N2 C21 C20 -137.07(18) . . . . ? C15 N2 C21 C20 -11.5(2) . . . . ? C16 N2 C21 C7 -11.8(2) . . . . ? C15 N2 C21 C7 113.74(19) . . . . ? C5 C7 C21 C20 -84.4(2) . . . . ? C17 C7 C21 C20 153.78(19) . . . . ? C8 C7 C21 C20 33.8(3) . . . . ? C5 C7 C21 N2 153.72(17) . . . . ? C17 C7 C21 N2 31.92(19) . . . . ? C8 C7 C21 N2 -88.1(2) . . . . ? C26A C25 N3 C27 -94.9(10) . . . . ? C26 C25 N3 C27 -138.8(2) . . . . ? C24 C25 N3 C27 93.1(3) . . . . ? C26A C25 C24 O6 -13.3(12) . . . . ? N3 C25 C24 O6 157.1(2) . . . . ? C26 C25 C24 O6 31.0(3) . . . . ? C26A C25 C24 O5 163.1(12) . . . . ? N3 C25 C24 O5 -26.6(3) . . . . ? C26 C25 C24 O5 -152.7(2) . . . . ? C26A O7 C26 C25 42.9(11) . . . . ? C26A C25 C26 O7 -50.2(12) . . . . ? N3 C25 C26 O7 56.5(3) . . . . ? C24 C25 C26 O7 -176.9(2) . . . . ? N3 C25 C26A O7 -34.2(17) . . . . ? C26 C25 C26A O7 57.2(13) . . . . ? C24 C25 C26A O7 135.8(10) . . . . ? C26 O7 C26A C25 -63.6(14) . . . . ? C25 N3 C27 O8 4.8(3) . . . . ? C25 N3 C27 C28 -176.42(19) . . . . ? O8 C27 C28 C29 13.6(3) . . . . ? N3 C27 C28 C29 -165.2(2) . . . . ? O8 C27 C28 C33 -166.3(2) . . . . ? N3 C27 C28 C33 14.9(3) . . . . ? C33 C28 C29 C30 0.1(4) . . . . ? C27 C28 C29 C30 -179.7(2) . . . . ? C28 C29 C30 C31 1.1(4) . . . . ? C29 C30 C31 C32 -1.4(4) . . . . ? C29 C30 C31 N4 177.7(2) . . . . ? O10 N4 C31 C30 -176.0(2) . . . . ? O9 N4 C31 C30 3.8(3) . . . . ? O10 N4 C31 C32 3.1(3) . . . . ? O9 N4 C31 C32 -177.1(2) . . . . ? C30 C31 C32 C33 0.4(4) . . . . ? N4 C31 C32 C33 -178.7(2) . . . . ? C31 C32 C33 C28 0.9(4) . . . . ? C29 C28 C33 C32 -1.1(4) . . . . ? C27 C28 C33 C32 178.7(2) . . . . ? 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 1.70 2.614(2) 168.8 . O7 H7 O9 0.85 2.22 2.998(2) 153.4 4_547 O7 H7 N3 0.85 2.39 2.842(3) 113.9 . N3 H3 O6 0.88 1.92 2.775(3) 163.1 4_457 O34 H34 O8 1.00 1.81 2.794(3) 167.1 . O35 H35 O4 0.93 1.87 2.800(3) 176.0 . _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 28.00 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.437 _refine_diff_density_min -0.213 _refine_diff_density_rms 0.044 # start Validation Reply Form _vrf_PLAT770_4 ; PROBLEM: Suspect C-H Bond in CIF: C26 -- H25A .. 1.31 Ang. RESPONSE: Two enantiomeric anions in equivalent positions ; # end Validation Reply Form #====== end data_5 _database_code_depnum_ccdc_archive 'CCDC 758146' #TrackingRef 'bialonska1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; brucinium N-(4-nitrobenzoyl)-D-serinate methanol disolvate ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C23 H27 N2 O4, C10 H9 N2 O6, 2(C H4 O)' _chemical_formula_sum 'C35 H44 N4 O12' _chemical_formula_weight 712.74 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 7.706(2) _cell_length_b 12.310(3) _cell_length_c 35.644(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3381.2(13) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3638 _cell_measurement_theta_min 2.70 _cell_measurement_theta_max 28.74 _exptl_crystal_description block _exptl_crystal_colour pale-yellow _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.400 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1512 _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 23340 _diffrn_reflns_av_R_equivalents 0.1239 _diffrn_reflns_av_sigmaI/netI 0.1198 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -45 _diffrn_reflns_limit_l_max 45 _diffrn_reflns_theta_min 2.70 _diffrn_reflns_theta_max 27.00 _reflns_number_total 4169 _reflns_number_gt 1916 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET) (compiled May 8 2007,13:10:02) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET) (compiled May 8 2007,13:10:02) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET) (compiled May 8 2007,13:10:02) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1223P)^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 4169 _refine_ls_number_parameters 457 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1481 _refine_ls_R_factor_gt 0.0713 _refine_ls_wR_factor_ref 0.2392 _refine_ls_wR_factor_gt 0.1624 _refine_ls_goodness_of_fit_ref 0.999 _refine_ls_restrained_S_all 0.999 _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 0.2642(7) 0.7195(4) 0.31479(13) 0.0313(12) Uani 1 1 d . . . O2 O 0.3078(7) 0.1384(4) 0.17864(13) 0.0309(12) Uani 1 1 d . . . O3 O 0.2551(7) 0.0233(4) 0.23833(14) 0.0353(13) Uani 1 1 d . . . O4 O 0.2809(8) 0.5339(4) 0.20078(14) 0.0385(14) Uani 1 1 d . . . N1 N 0.3357(7) 0.4662(4) 0.25866(16) 0.0247(14) Uani 1 1 d . . . N2 N 0.3128(9) 0.3743(5) 0.38450(17) 0.0334(16) Uani 1 1 d . . . H2 H 0.3131 0.3166 0.4013 0.040 Uiso 1 1 calc R . . C1 C 0.3262(10) 0.3073(6) 0.2143(2) 0.0279(17) Uani 1 1 d . . . H1 H 0.3393 0.3505 0.1924 0.034 Uiso 1 1 calc R . . C2 C 0.3084(10) 0.1956(6) 0.21229(19) 0.0305(18) Uani 1 1 d . . . C3 C 0.2815(10) 0.1332(6) 0.2443(2) 0.0290(17) Uani 1 1 d . . . C4 C 0.2849(10) 0.1810(6) 0.2797(2) 0.0284(17) Uani 1 1 d . . . H4 H 0.2718 0.1383 0.3017 0.034 Uiso 1 1 calc R . . C5 C 0.3079(9) 0.2922(6) 0.28200(19) 0.0239(16) Uani 1 1 d . . . C6 C 0.3239(9) 0.3532(5) 0.24986(19) 0.0227(15) Uani 1 1 d . . . C7 C 0.3323(10) 0.3623(6) 0.3161(2) 0.0267(16) Uani 1 1 d . . . C8 C 0.3127(10) 0.4794(6) 0.29972(18) 0.0294(18) Uani 1 1 d . . . H8 H 0.4076 0.5265 0.3098 0.035 Uiso 1 1 calc R . . C9 C 0.2852(10) 0.5467(6) 0.2352(2) 0.0297(17) Uani 1 1 d . . . C10 C 0.2416(11) 0.6551(6) 0.2524(2) 0.0298(17) Uani 1 1 d . . . H10A H 0.1625 0.6936 0.2350 0.036 Uiso 1 1 calc R . . H10B H 0.3499 0.6981 0.2539 0.036 Uiso 1 1 calc R . . C11 C 0.1570(10) 0.6549(6) 0.2917(2) 0.0279(17) Uani 1 1 d . . . H11 H 0.0392 0.6888 0.2901 0.033 Uiso 1 1 calc R . . C12 C 0.1910(10) 0.7459(6) 0.35127(19) 0.0328(18) Uani 1 1 d . . . H12A H 0.0635 0.7536 0.3492 0.039 Uiso 1 1 calc R . . H12B H 0.2393 0.8156 0.3603 0.039 Uiso 1 1 calc R . . C13 C 0.2352(11) 0.6554(7) 0.3788(2) 0.0370(19) Uani 1 1 d . . . H13 H 0.3080 0.6734 0.3994 0.044 Uiso 1 1 calc R . . C14 C 0.1812(10) 0.5545(7) 0.3764(2) 0.0321(18) Uani 1 1 d . . . C15 C 0.2351(12) 0.4697(6) 0.4039(2) 0.0353(19) Uani 1 1 d . . . H15A H 0.3209 0.5009 0.4215 0.042 Uiso 1 1 calc R . . H15B H 0.1329 0.4460 0.4186 0.042 Uiso 1 1 calc R . . C16 C 0.4996(10) 0.3948(7) 0.3725(2) 0.0328(19) Uani 1 1 d . . . H16A H 0.5817 0.3587 0.3899 0.039 Uiso 1 1 calc R . . H16B H 0.5252 0.4736 0.3720 0.039 Uiso 1 1 calc R . . C17 C 0.5125(10) 0.3460(7) 0.3332(2) 0.0312(18) Uani 1 1 d . . . H17A H 0.5420 0.2678 0.3345 0.037 Uiso 1 1 calc R . . H17B H 0.6021 0.3839 0.3182 0.037 Uiso 1 1 calc R . . C18 C 0.1389(10) 0.5364(6) 0.30525(19) 0.0276(17) Uani 1 1 d . . . H18 H 0.0560 0.5007 0.2875 0.033 Uiso 1 1 calc R . . C19 C 0.0643(10) 0.5184(6) 0.3449(2) 0.0318(18) Uani 1 1 d . . . H19 H -0.0504 0.5558 0.3471 0.038 Uiso 1 1 calc R . . C20 C 0.0383(10) 0.3939(6) 0.3484(2) 0.0306(18) Uani 1 1 d . . . H20A H -0.0269 0.3773 0.3717 0.037 Uiso 1 1 calc R . . H20B H -0.0298 0.3668 0.3268 0.037 Uiso 1 1 calc R . . C21 C 0.2129(10) 0.3381(7) 0.34944(19) 0.0331(18) Uani 1 1 d . . . H21 H 0.1938 0.2579 0.3509 0.040 Uiso 1 1 calc R . . C22 C 0.3331(11) 0.2021(6) 0.1456(2) 0.0328(18) Uani 1 1 d . . . H22A H 0.3300 0.1547 0.1235 0.049 Uiso 1 1 calc R . . H22B H 0.4458 0.2387 0.1469 0.049 Uiso 1 1 calc R . . H22C H 0.2407 0.2565 0.1436 0.049 Uiso 1 1 calc R . . C23 C 0.2321(12) -0.0421(6) 0.2709(2) 0.038(2) Uani 1 1 d . . . H23A H 0.2124 -0.1177 0.2634 0.057 Uiso 1 1 calc R . . H23B H 0.1317 -0.0158 0.2852 0.057 Uiso 1 1 calc R . . H23C H 0.3363 -0.0379 0.2866 0.057 Uiso 1 1 calc R . . O5 O 0.2841(7) 0.2215(4) 0.43460(14) 0.0358(13) Uani 1 1 d . . . O6 O 0.4199(7) 0.3407(4) 0.47103(14) 0.0344(13) Uani 1 1 d . . . O7 O 0.3479(7) 0.1370(4) 0.56429(14) 0.0381(13) Uani 1 1 d . . . H7A H 0.3101 0.0779 0.5558 0.057 Uiso 1 1 calc R . . O8 O 0.3922(7) -0.0356(5) 0.46427(15) 0.0382(14) Uani 1 1 d . . . O9 O -0.2588(8) -0.4036(4) 0.44121(15) 0.0409(14) Uani 1 1 d . . . O10 O -0.4514(8) -0.2791(5) 0.44925(17) 0.0447(16) Uani 1 1 d . . . N3 N 0.2193(8) 0.0861(4) 0.49255(16) 0.0280(14) Uani 1 1 d . . . H3 H 0.1153 0.0998 0.5016 0.034 Uiso 1 1 calc R . . N4 N -0.3032(9) -0.3096(5) 0.44891(17) 0.0327(15) Uani 1 1 d . . . C24 C 0.3513(11) 0.2519(6) 0.4651(2) 0.0327(18) Uani 1 1 d . . . C25 C 0.3543(11) 0.1666(6) 0.49707(19) 0.0303(18) Uani 1 1 d . . . H25 H 0.4684 0.1280 0.4958 0.036 Uiso 1 1 calc R . . C26 C 0.3409(11) 0.2185(6) 0.5353(2) 0.0327(18) Uani 1 1 d . . . H26A H 0.4374 0.2707 0.5387 0.039 Uiso 1 1 calc R . . H26B H 0.2303 0.2591 0.5372 0.039 Uiso 1 1 calc R . . C27 C 0.2470(11) -0.0086(6) 0.4751(2) 0.0290(17) Uani 1 1 d . . . C28 C 0.0971(10) -0.0835(6) 0.4693(2) 0.0266(16) Uani 1 1 d . . . C29 C 0.1380(11) -0.1898(6) 0.4606(2) 0.0332(18) Uani 1 1 d . . . H29 H 0.2564 -0.2110 0.4592 0.040 Uiso 1 1 calc R . . C30 C 0.0071(9) -0.2672(7) 0.4537(2) 0.0290(18) Uani 1 1 d . . . H30 H 0.0350 -0.3400 0.4472 0.035 Uiso 1 1 calc R . . C31 C -0.1637(10) -0.2333(6) 0.45669(19) 0.0279(17) Uani 1 1 d . . . C32 C -0.2077(11) -0.1291(6) 0.4664(2) 0.0342(19) Uani 1 1 d . . . H32 H -0.3264 -0.1094 0.4688 0.041 Uiso 1 1 calc R . . C33 C -0.0775(11) -0.0513(7) 0.4727(2) 0.037(2) Uani 1 1 d . . . H33 H -0.1066 0.0213 0.4792 0.044 Uiso 1 1 calc R . . O34 O 0.4885(9) -0.0789(6) 0.38959(18) 0.062(2) Uani 1 1 d . . . H34 H 0.4591 -0.0643 0.4133 0.093 Uiso 1 1 d . . . C34 C 0.4510(9) 0.0278(6) 0.37387(19) 0.092(4) Uani 1 1 d . . . H34A H 0.3265 0.0428 0.3761 0.138 Uiso 1 1 calc R . . H34B H 0.4846 0.0291 0.3474 0.138 Uiso 1 1 calc R . . H34C H 0.5166 0.0832 0.3876 0.138 Uiso 1 1 calc R . . O35 O 0.0163(9) 0.6091(6) 0.15416(19) 0.092(3) Uani 1 1 d R . . H35 H 0.1004 0.5866 0.1690 0.138 Uiso 1 1 d . . . C35 C 0.0528(19) 0.5767(14) 0.1168(3) 0.108(5) Uani 1 1 d . . . H35A H 0.1758 0.5573 0.1147 0.162 Uiso 1 1 calc R . . H35B H 0.0267 0.6367 0.0997 0.162 Uiso 1 1 calc R . . H35C H -0.0188 0.5137 0.1103 0.162 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.033(3) 0.032(3) 0.029(3) -0.007(2) -0.001(2) -0.003(3) O2 0.035(3) 0.034(3) 0.025(3) 0.000(2) -0.002(2) -0.004(3) O3 0.042(3) 0.031(3) 0.034(3) -0.003(2) 0.002(3) 0.004(3) O4 0.051(4) 0.037(3) 0.027(3) 0.003(2) -0.001(3) 0.004(3) N1 0.026(3) 0.019(3) 0.030(3) -0.002(3) -0.010(3) -0.002(3) N2 0.041(4) 0.033(4) 0.026(3) 0.003(3) -0.006(3) 0.004(3) C1 0.029(4) 0.025(4) 0.030(4) 0.002(3) -0.001(3) 0.001(3) C2 0.029(4) 0.040(4) 0.023(4) -0.003(3) -0.002(3) 0.007(4) C3 0.030(4) 0.030(4) 0.027(4) -0.001(3) 0.000(3) 0.009(4) C4 0.036(5) 0.023(4) 0.026(4) 0.001(3) 0.000(4) -0.005(3) C5 0.026(4) 0.021(3) 0.024(4) -0.001(3) -0.004(3) 0.000(3) C6 0.022(4) 0.018(3) 0.029(4) -0.006(3) -0.006(3) 0.002(3) C7 0.027(4) 0.025(4) 0.028(4) 0.005(3) -0.013(3) -0.004(3) C8 0.032(4) 0.040(4) 0.016(3) -0.003(3) -0.002(3) 0.000(4) C9 0.034(4) 0.028(4) 0.027(4) 0.007(3) -0.004(4) 0.002(4) C10 0.036(4) 0.023(4) 0.030(4) 0.001(3) 0.002(4) 0.003(4) C11 0.030(4) 0.023(4) 0.030(4) 0.004(3) -0.003(3) -0.006(4) C12 0.033(4) 0.043(5) 0.023(4) -0.015(3) 0.003(3) 0.009(4) C13 0.041(5) 0.045(5) 0.025(4) 0.002(4) 0.002(4) -0.003(4) C14 0.033(5) 0.041(5) 0.022(4) -0.001(3) -0.001(3) 0.001(4) C15 0.056(5) 0.028(4) 0.022(4) -0.004(3) 0.002(4) 0.003(4) C16 0.032(5) 0.033(4) 0.034(4) 0.005(4) -0.010(4) -0.005(4) C17 0.039(5) 0.026(4) 0.028(4) -0.001(3) -0.003(3) 0.001(4) C18 0.029(4) 0.026(4) 0.028(4) 0.007(3) -0.004(3) 0.002(4) C19 0.029(4) 0.043(5) 0.024(4) 0.004(4) 0.000(3) 0.006(4) C20 0.043(5) 0.023(4) 0.026(4) 0.001(3) 0.006(4) 0.002(4) C21 0.039(5) 0.041(4) 0.019(4) -0.008(3) -0.001(3) -0.006(4) C22 0.044(5) 0.028(4) 0.027(4) 0.002(3) -0.002(4) -0.008(4) C23 0.050(5) 0.025(4) 0.039(4) 0.010(4) 0.007(4) -0.002(4) O5 0.046(3) 0.036(3) 0.026(3) 0.002(2) -0.008(3) -0.008(3) O6 0.037(3) 0.033(3) 0.034(3) 0.000(3) -0.007(3) 0.000(3) O7 0.054(4) 0.032(3) 0.028(3) 0.008(2) -0.005(3) -0.005(3) O8 0.035(3) 0.040(3) 0.039(3) -0.008(3) -0.004(3) -0.001(3) O9 0.054(4) 0.033(3) 0.035(3) -0.007(3) 0.001(3) 0.004(3) O10 0.033(3) 0.048(4) 0.052(4) -0.001(3) -0.007(3) 0.009(3) N3 0.035(4) 0.020(3) 0.030(3) 0.001(3) -0.001(3) -0.006(3) N4 0.035(4) 0.034(4) 0.028(3) 0.000(3) -0.003(3) -0.003(3) C24 0.037(4) 0.027(4) 0.034(4) -0.004(4) 0.002(4) -0.007(4) C25 0.039(5) 0.030(4) 0.022(4) 0.000(3) 0.003(3) 0.001(4) C26 0.032(4) 0.039(4) 0.027(4) 0.007(4) 0.000(3) 0.002(4) C27 0.033(4) 0.022(4) 0.032(4) -0.006(3) -0.006(4) 0.002(4) C28 0.031(4) 0.028(4) 0.021(4) 0.001(3) 0.002(3) 0.005(3) C29 0.031(4) 0.029(4) 0.039(4) -0.007(4) -0.003(4) 0.002(4) C30 0.022(4) 0.038(4) 0.027(4) -0.009(4) 0.002(3) 0.004(4) C31 0.040(5) 0.020(4) 0.023(4) 0.005(3) -0.005(3) -0.009(4) C32 0.034(5) 0.038(4) 0.031(4) 0.001(4) 0.004(4) 0.002(4) C33 0.035(4) 0.041(5) 0.034(5) -0.008(4) -0.005(4) 0.005(4) O34 0.065(5) 0.058(4) 0.063(4) -0.013(4) 0.005(4) 0.000(4) C34 0.129(12) 0.076(9) 0.071(8) 0.021(7) -0.001(8) -0.017(9) O35 0.086(6) 0.129(8) 0.060(5) 0.008(5) 0.002(4) 0.057(6) C35 0.105(10) 0.175(15) 0.043(7) -0.023(8) -0.007(7) 0.055(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C11 1.411(9) . ? O1 C12 1.454(8) . ? O2 C2 1.391(8) . ? O2 C22 1.429(8) . ? O3 C3 1.384(8) . ? O3 C23 1.424(8) . ? O4 C9 1.239(8) . ? N1 C9 1.353(9) . ? N1 C6 1.429(8) . ? N1 C8 1.483(9) . ? N2 C15 1.488(9) . ? N2 C16 1.523(10) . ? N2 C21 1.534(9) . ? N2 H2 0.9300 . ? C1 C2 1.383(10) . ? C1 C6 1.389(10) . ? C1 H1 0.9500 . ? C2 C3 1.392(10) . ? C3 C4 1.391(10) . ? C4 C5 1.383(9) . ? C4 H4 0.9500 . ? C5 C6 1.375(9) . ? C5 C7 1.502(10) . ? C7 C17 1.531(10) . ? C7 C21 1.533(10) . ? C7 C8 1.562(10) . ? C8 C18 1.525(10) . ? C8 H8 1.0000 . ? C9 C10 1.506(10) . ? C10 C11 1.546(10) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C18 1.543(10) . ? C11 H11 1.0000 . ? C12 C13 1.523(11) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.312(11) . ? C13 H13 0.9500 . ? C14 C15 1.490(10) . ? C14 C19 1.508(10) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 C17 1.528(10) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 C19 1.541(10) . ? C18 H18 1.0000 . ? C19 C20 1.550(10) . ? C19 H19 1.0000 . ? C20 C21 1.511(11) . ? 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(9) . ? O6 C24 1.232(8) . ? O7 C26 1.442(8) . ? O7 H7A 0.8400 . ? O8 C27 1.230(9) . ? O9 N4 1.237(8) . ? O10 N4 1.202(8) . ? N3 C27 1.338(9) . ? N3 C25 1.446(9) . ? N3 H3 0.8800 . ? N4 C31 1.455(9) . ? C24 C25 1.549(10) . ? C25 C26 1.508(10) . ? C25 H25 1.0000 . ? C26 H26A 0.9900 . ? C26 H26B 0.9900 . ? C27 C28 1.493(11) . ? C28 C29 1.381(10) . ? C28 C33 1.408(11) . ? C29 C30 1.409(11) . ? C29 H29 0.9500 . ? C30 C31 1.385(11) . ? C30 H30 0.9500 . ? C31 C32 1.372(10) . ? C32 C33 1.405(11) . ? C32 H32 0.9500 . ? C33 H33 0.9500 . ? O34 C34 1.457(10) . ? O34 H34 0.8918 . ? C34 H34A 0.9800 . ? C34 H34B 0.9800 . ? C34 H34C 0.9800 . ? O35 C35 1.417(12) . ? O35 H35 0.8808 . ? C35 H35A 0.9800 . ? C35 H35B 0.9800 . ? C35 H35C 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 114.8(6) . . ? C2 O2 C22 115.7(5) . . ? C3 O3 C23 116.4(6) . . ? C9 N1 C6 124.0(6) . . ? C9 N1 C8 119.6(6) . . ? C6 N1 C8 108.4(5) . . ? C15 N2 C16 112.3(6) . . ? C15 N2 C21 113.9(6) . . ? C16 N2 C21 107.1(6) . . ? C15 N2 H2 107.7 . . ? C16 N2 H2 107.7 . . ? C21 N2 H2 107.7 . . ? C2 C1 C6 116.7(7) . . ? C2 C1 H1 121.7 . . ? C6 C1 H1 121.7 . . ? C1 C2 O2 123.2(6) . . ? C1 C2 C3 121.5(7) . . ? O2 C2 C3 115.2(7) . . ? O3 C3 C4 123.8(7) . . ? O3 C3 C2 115.8(6) . . ? C4 C3 C2 120.4(7) . . ? C5 C4 C3 118.5(7) . . ? C5 C4 H4 120.8 . . ? C3 C4 H4 120.8 . . ? C6 C5 C4 120.1(6) . . ? C6 C5 C7 110.4(6) . . ? C4 C5 C7 129.3(6) . . ? C5 C6 C1 122.7(6) . . ? C5 C6 N1 110.7(6) . . ? C1 C6 N1 126.5(6) . . ? C5 C7 C17 111.2(6) . . ? C5 C7 C21 116.1(6) . . ? C17 C7 C21 102.1(6) . . ? C5 C7 C8 102.5(5) . . ? C17 C7 C8 111.0(6) . . ? C21 C7 C8 114.2(6) . . ? N1 C8 C18 106.5(6) . . ? N1 C8 C7 104.8(5) . . ? C18 C8 C7 117.5(6) . . ? N1 C8 H8 109.3 . . ? C18 C8 H8 109.3 . . ? C7 C8 H8 109.3 . . ? O4 C9 N1 121.8(7) . . ? O4 C9 C10 120.6(6) . . ? N1 C9 C10 117.5(6) . . ? C9 C10 C11 117.5(6) . . ? 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 113.8(6) . . ? O1 C11 C10 106.3(6) . . ? C18 C11 C10 108.8(6) . . ? O1 C11 H11 109.3 . . ? C18 C11 H11 109.3 . . ? C10 C11 H11 109.3 . . ? O1 C12 C13 109.0(6) . . ? O1 C12 H12A 109.9 . . ? C13 C12 H12A 109.9 . . ? O1 C12 H12B 109.9 . . ? C13 C12 H12B 109.9 . . ? H12A C12 H12B 108.3 . . ? C14 C13 C12 125.4(7) . . ? C14 C13 H13 117.3 . . ? C12 C13 H13 117.3 . . ? C13 C14 C15 122.2(7) . . ? C13 C14 C19 121.1(7) . . ? C15 C14 C19 116.7(7) . . ? N2 C15 C14 111.1(6) . . ? N2 C15 H15A 109.4 . . ? C14 C15 H15A 109.4 . . ? N2 C15 H15B 109.4 . . ? C14 C15 H15B 109.4 . . ? H15A C15 H15B 108.0 . . ? N2 C16 C17 104.7(6) . . ? N2 C16 H16A 110.8 . . ? C17 C16 H16A 110.8 . . ? N2 C16 H16B 110.8 . . ? C17 C16 H16B 110.8 . . ? H16A C16 H16B 108.9 . . ? C16 C17 C7 104.8(6) . . ? C16 C17 H17A 110.8 . . ? C7 C17 H17A 110.8 . . ? C16 C17 H17B 110.8 . . ? C7 C17 H17B 110.8 . . ? H17A C17 H17B 108.9 . . ? C8 C18 C19 112.3(6) . . ? C8 C18 C11 108.4(6) . . ? C19 C18 C11 117.2(6) . . ? C8 C18 H18 106.1 . . ? C19 C18 H18 106.1 . . ? C11 C18 H18 106.1 . . ? C14 C19 C18 114.7(6) . . ? C14 C19 C20 107.9(6) . . ? C18 C19 C20 105.4(6) . . ? C14 C19 H19 109.5 . . ? C18 C19 H19 109.5 . . ? C20 C19 H19 109.5 . . ? C21 C20 C19 109.6(6) . . ? C21 C20 H20A 109.7 . . ? C19 C20 H20A 109.7 . . ? C21 C20 H20B 109.7 . . ? C19 C20 H20B 109.7 . . ? H20A C20 H20B 108.2 . . ? C20 C21 C7 115.3(6) . . ? C20 C21 N2 109.5(6) . . ? C7 C21 N2 105.9(6) . . ? 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 . . ? C26 O7 H7A 109.5 . . ? C27 N3 C25 122.2(7) . . ? C27 N3 H3 118.9 . . ? C25 N3 H3 118.9 . . ? O10 N4 O9 123.8(7) . . ? O10 N4 C31 119.9(7) . . ? O9 N4 C31 116.2(7) . . ? O6 C24 O5 125.9(7) . . ? O6 C24 C25 118.0(7) . . ? O5 C24 C25 116.0(6) . . ? N3 C25 C26 110.0(6) . . ? N3 C25 C24 111.8(6) . . ? C26 C25 C24 112.0(6) . . ? N3 C25 H25 107.6 . . ? C26 C25 H25 107.6 . . ? C24 C25 H25 107.6 . . ? O7 C26 C25 110.5(6) . . ? O7 C26 H26A 109.6 . . ? C25 C26 H26A 109.6 . . ? O7 C26 H26B 109.6 . . ? C25 C26 H26B 109.6 . . ? H26A C26 H26B 108.1 . . ? O8 C27 N3 121.8(7) . . ? O8 C27 C28 119.6(6) . . ? N3 C27 C28 118.6(7) . . ? C29 C28 C33 120.3(7) . . ? C29 C28 C27 116.1(7) . . ? C33 C28 C27 123.6(7) . . ? C28 C29 C30 121.1(7) . . ? C28 C29 H29 119.5 . . ? C30 C29 H29 119.5 . . ? C31 C30 C29 117.6(7) . . ? C31 C30 H30 121.2 . . ? C29 C30 H30 121.2 . . ? C32 C31 C30 122.5(7) . . ? C32 C31 N4 118.0(7) . . ? C30 C31 N4 119.5(7) . . ? C31 C32 C33 120.1(7) . . ? C31 C32 H32 120.0 . . ? C33 C32 H32 120.0 . . ? C32 C33 C28 118.5(7) . . ? C32 C33 H33 120.8 . . ? C28 C33 H33 120.8 . . ? C34 O34 H34 97.5 . . ? O34 C34 H34A 109.5 . . ? O34 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? O34 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? C35 O35 H35 109.1 . . ? 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 . . ? 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 179.8(6) . . . . ? C6 C1 C2 C3 2.9(12) . . . . ? C22 O2 C2 C1 2.1(11) . . . . ? C22 O2 C2 C3 179.2(7) . . . . ? C23 O3 C3 C4 -0.6(11) . . . . ? C23 O3 C3 C2 178.3(7) . . . . ? C1 C2 C3 O3 176.1(7) . . . . ? O2 C2 C3 O3 -1.0(10) . . . . ? C1 C2 C3 C4 -4.9(12) . . . . ? O2 C2 C3 C4 177.9(7) . . . . ? O3 C3 C4 C5 -178.3(7) . . . . ? C2 C3 C4 C5 2.8(11) . . . . ? C3 C4 C5 C6 1.0(11) . . . . ? C3 C4 C5 C7 -173.9(7) . . . . ? C4 C5 C6 C1 -3.1(11) . . . . ? C7 C5 C6 C1 172.8(7) . . . . ? C4 C5 C6 N1 176.5(7) . . . . ? C7 C5 C6 N1 -7.7(8) . . . . ? C2 C1 C6 C5 1.1(11) . . . . ? C2 C1 C6 N1 -178.4(7) . . . . ? C9 N1 C6 C5 -152.9(7) . . . . ? C8 N1 C6 C5 -4.4(8) . . . . ? C9 N1 C6 C1 26.6(12) . . . . ? C8 N1 C6 C1 175.1(7) . . . . ? C6 C5 C7 C17 -103.1(7) . . . . ? C4 C5 C7 C17 72.3(10) . . . . ? C6 C5 C7 C21 140.9(7) . . . . ? C4 C5 C7 C21 -43.8(11) . . . . ? C6 C5 C7 C8 15.6(8) . . . . ? C4 C5 C7 C8 -169.0(8) . . . . ? C9 N1 C8 C18 38.8(8) . . . . ? C6 N1 C8 C18 -111.3(6) . . . . ? C9 N1 C8 C7 163.9(6) . . . . ? C6 N1 C8 C7 13.8(7) . . . . ? C5 C7 C8 N1 -17.3(7) . . . . ? C17 C7 C8 N1 101.5(7) . . . . ? C21 C7 C8 N1 -143.8(6) . . . . ? C5 C7 C8 C18 100.6(7) . . . . ? C17 C7 C8 C18 -140.6(7) . . . . ? C21 C7 C8 C18 -25.9(9) . . . . ? C6 N1 C9 O4 -25.3(12) . . . . ? C8 N1 C9 O4 -170.5(7) . . . . ? C6 N1 C9 C10 157.5(7) . . . . ? C8 N1 C9 C10 12.2(10) . . . . ? O4 C9 C10 C11 148.7(8) . . . . ? N1 C9 C10 C11 -33.9(11) . . . . ? C12 O1 C11 C18 -70.8(8) . . . . ? C12 O1 C11 C10 169.4(6) . . . . ? C9 C10 C11 O1 124.0(7) . . . . ? C9 C10 C11 C18 1.0(10) . . . . ? C11 O1 C12 C13 87.1(7) . . . . ? O1 C12 C13 C14 -64.3(10) . . . . ? C12 C13 C14 C15 177.9(7) . . . . ? C12 C13 C14 C19 -0.4(13) . . . . ? C16 N2 C15 C14 78.5(8) . . . . ? C21 N2 C15 C14 -43.6(9) . . . . ? C13 C14 C15 N2 -125.4(8) . . . . ? C19 C14 C15 N2 53.0(9) . . . . ? C15 N2 C16 C17 -138.1(6) . . . . ? C21 N2 C16 C17 -12.3(8) . . . . ? N2 C16 C17 C7 32.5(8) . . . . ? C5 C7 C17 C16 -164.1(6) . . . . ? C21 C7 C17 C16 -39.7(7) . . . . ? C8 C7 C17 C16 82.4(7) . . . . ? N1 C8 C18 C19 158.5(6) . . . . ? C7 C8 C18 C19 41.5(9) . . . . ? N1 C8 C18 C11 -70.4(7) . . . . ? C7 C8 C18 C11 172.6(6) . . . . ? O1 C11 C18 C8 -69.3(7) . . . . ? C10 C11 C18 C8 49.0(8) . . . . ? O1 C11 C18 C19 59.0(9) . . . . ? C10 C11 C18 C19 177.3(6) . . . . ? C13 C14 C19 C18 58.0(10) . . . . ? C15 C14 C19 C18 -120.4(7) . . . . ? C13 C14 C19 C20 175.2(7) . . . . ? C15 C14 C19 C20 -3.3(9) . . . . ? C8 C18 C19 C14 57.5(9) . . . . ? C11 C18 C19 C14 -68.9(9) . . . . ? C8 C18 C19 C20 -61.1(8) . . . . ? C11 C18 C19 C20 172.5(7) . . . . ? C14 C19 C20 C21 -54.6(8) . . . . ? C18 C19 C20 C21 68.5(8) . . . . ? C19 C20 C21 C7 -56.0(8) . . . . ? C19 C20 C21 N2 63.4(8) . . . . ? C5 C7 C21 C20 -85.9(8) . . . . ? C17 C7 C21 C20 153.0(7) . . . . ? C8 C7 C21 C20 33.1(8) . . . . ? C5 C7 C21 N2 152.8(6) . . . . ? C17 C7 C21 N2 31.7(7) . . . . ? C8 C7 C21 N2 -88.2(7) . . . . ? C15 N2 C21 C20 -12.4(8) . . . . ? C16 N2 C21 C20 -137.3(6) . . . . ? C15 N2 C21 C7 112.5(7) . . . . ? C16 N2 C21 C7 -12.3(8) . . . . ? C27 N3 C25 C26 -141.0(7) . . . . ? C27 N3 C25 C24 93.8(8) . . . . ? O6 C24 C25 N3 158.2(7) . . . . ? O5 C24 C25 N3 -24.7(10) . . . . ? O6 C24 C25 C26 34.2(10) . . . . ? O5 C24 C25 C26 -148.7(7) . . . . ? N3 C25 C26 O7 56.2(8) . . . . ? C24 C25 C26 O7 -178.7(6) . . . . ? C25 N3 C27 O8 5.3(11) . . . . ? C25 N3 C27 C28 -175.8(6) . . . . ? O8 C27 C28 C29 15.6(10) . . . . ? N3 C27 C28 C29 -163.4(7) . . . . ? O8 C27 C28 C33 -165.1(7) . . . . ? N3 C27 C28 C33 15.9(11) . . . . ? C33 C28 C29 C30 2.1(12) . . . . ? C27 C28 C29 C30 -178.5(7) . . . . ? C28 C29 C30 C31 -1.2(11) . . . . ? C29 C30 C31 C32 -0.7(11) . . . . ? C29 C30 C31 N4 178.5(6) . . . . ? O10 N4 C31 C32 3.7(10) . . . . ? O9 N4 C31 C32 -178.1(6) . . . . ? O10 N4 C31 C30 -175.5(7) . . . . ? O9 N4 C31 C30 2.6(9) . . . . ? C30 C31 C32 C33 1.7(11) . . . . ? N4 C31 C32 C33 -177.5(7) . . . . ? C31 C32 C33 C28 -0.7(11) . . . . ? C29 C28 C33 C32 -1.1(12) . . . . ? C27 C28 C33 C32 179.6(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 H2 O5 0.93 1.68 2.603(8) 170.7 . O7 H7A O9 0.84 2.21 2.995(8) 155.0 4_546 N3 H3 O6 0.88 1.94 2.796(8) 164.7 4_456 O34 H34 O8 0.89 1.92 2.814(8) 178.7 . O35 H35 O4 0.88 1.91 2.789(8) 178.5 . _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.473 _refine_diff_density_min -0.425 _refine_diff_density_rms 0.105 #===== end data_6 _database_code_depnum_ccdc_archive 'CCDC 758147' #TrackingRef 'bialonska1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; brucinium N-(4-nitrobenzoyl)-L-serinate methanol tetrasolvate ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C23 H27 N2 O4, C10 H9 N2 O6, 4(C H4 O)' _chemical_formula_sum 'C37 H52 N4 O14' _chemical_formula_weight 776.83 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 10.494(2) _cell_length_b 13.966(2) _cell_length_c 26.751(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3920.6(10) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 8757 _cell_measurement_theta_min 3.00 _cell_measurement_theta_max 36.63 _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.40 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.316 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1656 _exptl_absorpt_coefficient_mu 0.101 _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 72076 _diffrn_reflns_av_R_equivalents 0.1059 _diffrn_reflns_av_sigmaI/netI 0.1241 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -33 _diffrn_reflns_limit_l_max 44 _diffrn_reflns_theta_min 3.00 _diffrn_reflns_theta_max 36.00 _reflns_number_total 9944 _reflns_number_gt 5381 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET) (compiled May 8 2007,13:10:02) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET) (compiled May 8 2007,13:10:02) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET) (compiled May 8 2007,13:10:02) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1169P)^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 9944 _refine_ls_number_parameters 497 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1372 _refine_ls_R_factor_gt 0.0768 _refine_ls_wR_factor_ref 0.2285 _refine_ls_wR_factor_gt 0.2104 _refine_ls_goodness_of_fit_ref 1.007 _refine_ls_restrained_S_all 1.007 _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 0.6319(2) 0.91635(18) 0.65021(9) 0.0210(5) Uani 1 1 d . . . O2 O -0.0360(2) 0.56010(19) 0.70229(9) 0.0238(5) Uani 1 1 d . . . O3 O -0.0671(2) 0.64094(18) 0.78824(9) 0.0230(5) Uani 1 1 d . . . O4 O 0.3179(3) 0.6938(2) 0.60204(9) 0.0298(6) Uani 1 1 d . . . N1 N 0.3665(3) 0.74002(19) 0.68120(10) 0.0168(5) Uani 1 1 d . . . N2 N 0.4519(3) 0.9267(2) 0.82030(10) 0.0202(6) Uani 1 1 d . . . H2 H 0.4322 0.9424 0.8515 0.024 Uiso 1 1 d . . . C1 C 0.1626(3) 0.6431(2) 0.68622(11) 0.0166(6) Uani 1 1 d . . . H1 H 0.1729 0.6144 0.6543 0.020 Uiso 1 1 calc R . . C2 C 0.0585(3) 0.6224(2) 0.71623(12) 0.0190(6) Uani 1 1 d . . . C3 C 0.0425(3) 0.6649(2) 0.76359(12) 0.0175(6) Uani 1 1 d . . . C4 C 0.1350(3) 0.7281(2) 0.78168(11) 0.0172(6) Uani 1 1 d . . . H4 H 0.1261 0.7559 0.8139 0.021 Uiso 1 1 calc R . . C5 C 0.2402(3) 0.7500(2) 0.75214(12) 0.0174(6) Uani 1 1 d . . . C6 C 0.2523(3) 0.7085(2) 0.70522(11) 0.0162(6) Uani 1 1 d . . . C7 C 0.3572(3) 0.8080(2) 0.76480(11) 0.0165(6) Uani 1 1 d . . . C8 C 0.4270(3) 0.8149(2) 0.71285(11) 0.0156(6) Uani 1 1 d . . . H8 H 0.5198 0.8008 0.7171 0.019 Uiso 1 1 calc R . . C9 C 0.3836(3) 0.7418(3) 0.63104(12) 0.0218(7) Uani 1 1 d . . . C10 C 0.4916(3) 0.8057(3) 0.61310(12) 0.0220(7) Uani 1 1 d . . . H10A H 0.4820 0.8155 0.5766 0.026 Uiso 1 1 calc R . . H10B H 0.5732 0.7717 0.6186 0.026 Uiso 1 1 calc R . . C11 C 0.4997(3) 0.9053(2) 0.63879(12) 0.0186(6) Uani 1 1 d . . . H11 H 0.4740 0.9558 0.6143 0.022 Uiso 1 1 calc R . . C12 C 0.6655(3) 1.0111(3) 0.66868(13) 0.0226(7) Uani 1 1 d . . . H12A H 0.6099 1.0595 0.6527 0.027 Uiso 1 1 calc R . . H12B H 0.7548 1.0257 0.6595 0.027 Uiso 1 1 calc R . . C13 C 0.6509(3) 1.0169(2) 0.72446(12) 0.0211(6) Uani 1 1 d . . . H13 H 0.7245 1.0259 0.7446 0.025 Uiso 1 1 calc R . . C14 C 0.5363(3) 1.0097(2) 0.74666(12) 0.0195(6) Uani 1 1 d . . . C15 C 0.5238(3) 1.0128(3) 0.80280(12) 0.0211(6) Uani 1 1 d . . . H15A H 0.6095 1.0138 0.8183 0.025 Uiso 1 1 calc R . . H15B H 0.4782 1.0717 0.8129 0.025 Uiso 1 1 calc R . . C16 C 0.5319(4) 0.8368(3) 0.82104(13) 0.0233(7) Uani 1 1 d . . . H16A H 0.5641 0.8237 0.8552 0.028 Uiso 1 1 calc R . . H16B H 0.6054 0.8428 0.7980 0.028 Uiso 1 1 calc R . . C17 C 0.4425(3) 0.7576(3) 0.80387(12) 0.0204(6) Uani 1 1 d . . . H17A H 0.3912 0.7327 0.8321 0.025 Uiso 1 1 calc R . . H17B H 0.4905 0.7040 0.7886 0.025 Uiso 1 1 calc R . . C18 C 0.4095(3) 0.9089(2) 0.68388(11) 0.0165(6) Uani 1 1 d . . . H18 H 0.3214 0.9064 0.6697 0.020 Uiso 1 1 calc R . . C19 C 0.4129(3) 0.9986(2) 0.71782(12) 0.0197(6) Uani 1 1 d . . . H19 H 0.3985 1.0570 0.6969 0.024 Uiso 1 1 calc R . . C20 C 0.3007(3) 0.9869(2) 0.75494(13) 0.0205(6) Uani 1 1 d . . . H20A H 0.2890 1.0465 0.7744 0.025 Uiso 1 1 calc R . . H20B H 0.2209 0.9736 0.7365 0.025 Uiso 1 1 calc R . . C21 C 0.3314(3) 0.9044(2) 0.78962(12) 0.0188(6) Uani 1 1 d . . . H21 H 0.2585 0.8963 0.8133 0.023 Uiso 1 1 calc R . . C22 C -0.0216(4) 0.5142(4) 0.65441(15) 0.0379(10) Uani 1 1 d . . . H22A H -0.0940 0.4714 0.6485 0.057 Uiso 1 1 calc R . . H22B H 0.0577 0.4771 0.6541 0.057 Uiso 1 1 calc R . . H22C H -0.0186 0.5630 0.6281 0.057 Uiso 1 1 calc R . . C23 C -0.0911(4) 0.6894(3) 0.83491(14) 0.0343(9) Uani 1 1 d . . . H23A H -0.1715 0.6664 0.8492 0.051 Uiso 1 1 calc R . . H23B H -0.0967 0.7585 0.8290 0.051 Uiso 1 1 calc R . . H23C H -0.0213 0.6762 0.8583 0.051 Uiso 1 1 calc R . . O5 O 0.3416(4) 0.9338(3) 0.90945(11) 0.0457(9) Uani 1 1 d . . . O6 O 0.5017(4) 1.0179(4) 0.94195(13) 0.0701(14) Uani 1 1 d . . . O7 O 0.2022(7) 1.1328(3) 0.95099(14) 0.094(2) Uani 1 1 d . A 1 H7 H 0.1947 1.1792 0.9708 0.141 Uiso 1 1 calc R A 1 O8 O 0.2663(3) 1.0035(2) 1.09179(9) 0.0293(6) Uani 1 1 d . A 1 O9 O 0.7187(3) 1.1926(3) 1.25060(14) 0.0492(9) Uani 1 1 d . A 1 O10 O 0.7786(3) 1.2922(2) 1.19239(16) 0.0504(10) Uani 1 1 d . A 1 N3 N 0.3829(4) 1.0545(3) 1.02544(11) 0.0328(8) Uani 1 1 d . A 1 H3 H 0.4459 1.0907 1.0148 0.039 Uiso 1 1 calc R A 1 N4 N 0.7098(4) 1.2269(3) 1.20871(17) 0.0418(10) Uani 1 1 d . A 1 C24 C 0.3951(5) 0.9834(4) 0.94323(16) 0.0396(10) Uani 1 1 d . A 1 C25 C 0.3104(4) 1.0001(3) 0.99022(13) 0.0344(9) Uani 1 1 d . A 1 H25 H 0.2917 0.9363 1.0055 0.041 Uiso 1 1 calc R A 1 C26 C 0.1845(6) 1.0469(4) 0.97708(17) 0.0510(14) Uani 1 1 d . A 1 H26A H 0.1335 1.0024 0.9563 0.061 Uiso 1 1 calc R A 1 H26B H 0.1362 1.0598 1.0082 0.061 Uiso 1 1 calc R A 1 C27 C 0.3559(4) 1.0512(3) 1.07503(13) 0.0259(7) Uani 1 1 d . A 1 C28 C 0.4444(3) 1.1043(3) 1.10939(13) 0.0230(7) Uani 1 1 d . A 1 C29 C 0.4562(4) 1.0687(3) 1.15764(12) 0.0236(7) Uani 1 1 d . A 1 H29 H 0.4054 1.0158 1.1678 0.028 Uiso 1 1 calc R A 1 C30 C 0.5415(4) 1.1096(3) 1.19128(14) 0.0281(8) Uani 1 1 d . A 1 H30 H 0.5505 1.0853 1.2243 0.034 Uiso 1 1 calc R A 1 C31 C 0.6128(4) 1.1871(3) 1.17484(15) 0.0283(8) Uani 1 1 d . A 1 C32 C 0.6002(4) 1.2259(3) 1.12804(16) 0.0323(9) Uani 1 1 d . A 1 H32 H 0.6493 1.2799 1.1183 0.039 Uiso 1 1 calc R A 1 C33 C 0.5135(4) 1.1841(3) 1.09506(15) 0.0314(8) Uani 1 1 d . A 1 H33 H 0.5018 1.2105 1.0627 0.038 Uiso 1 1 calc R A 1 O34 O 0.1434(4) 0.8088(3) 0.90691(14) 0.0601(11) Uani 1 1 d . B 1 H34 H 0.2059 0.8461 0.9091 0.090 Uiso 1 1 calc R B 1 C34 C 0.1686(8) 0.7247(5) 0.9345(3) 0.0753(19) Uani 1 1 d . B 1 H34A H 0.0911 0.7045 0.9520 0.113 Uiso 1 1 calc R B 1 H34B H 0.2361 0.7374 0.9590 0.113 Uiso 1 1 calc R B 1 H34C H 0.1962 0.6738 0.9117 0.113 Uiso 1 1 calc R B 1 O35 O 0.7308(4) 0.9609(3) 0.89909(13) 0.0533(10) Uani 1 1 d . C 1 H35 H 0.6638 0.9813 0.9126 0.080 Uiso 1 1 calc R C 1 C35 C 0.7845(8) 0.8831(5) 0.9296(2) 0.072(2) Uani 1 1 d . C 1 H35A H 0.8756 0.8765 0.9223 0.108 Uiso 1 1 calc R C 1 H35B H 0.7408 0.8230 0.9216 0.108 Uiso 1 1 calc R C 1 H35C H 0.7729 0.8980 0.9651 0.108 Uiso 1 1 calc R C 1 O36 O 0.3152(5) 0.6991(3) 0.50300(12) 0.0724(14) Uani 1 1 d . D 1 H36 H 0.3280 0.6967 0.5340 0.109 Uiso 1 1 calc R D 1 C36 C 0.2314(7) 0.6216(5) 0.4884(2) 0.0669(18) Uani 1 1 d . D 1 H36A H 0.1471 0.6314 0.5034 0.100 Uiso 1 1 calc R D 1 H36B H 0.2667 0.5606 0.5001 0.100 Uiso 1 1 calc R D 1 H36C H 0.2235 0.6202 0.4519 0.100 Uiso 1 1 calc R D 1 O37 O 0.1017(4) 0.8475(3) 1.09788(16) 0.0628(11) Uani 1 1 d . E 1 H37 H 0.1479 0.8962 1.0947 0.094 Uiso 1 1 calc R E 1 C37 C 0.0187(7) 0.8405(6) 1.0567(3) 0.078(2) Uani 1 1 d . E 1 H37A H 0.0685 0.8373 1.0257 0.118 Uiso 1 1 calc R E 1 H37B H -0.0369 0.8969 1.0557 0.118 Uiso 1 1 calc R E 1 H37C H -0.0334 0.7826 1.0599 0.118 Uiso 1 1 calc R E 1 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 0.0168(11) 0.0204(12) 0.0257(11) -0.0023(9) 0.0010(9) -0.0019(9) O2 0.0183(12) 0.0260(13) 0.0271(12) -0.0052(10) 0.0023(10) -0.0098(10) O3 0.0199(12) 0.0250(13) 0.0239(11) -0.0031(10) 0.0058(9) -0.0065(9) O4 0.0302(14) 0.0383(16) 0.0208(11) -0.0057(11) 0.0039(10) -0.0114(12) N1 0.0161(13) 0.0167(13) 0.0175(11) -0.0031(10) 0.0010(10) -0.0051(10) N2 0.0229(14) 0.0190(14) 0.0186(12) -0.0046(10) -0.0043(11) -0.0028(11) C1 0.0146(14) 0.0184(15) 0.0169(13) -0.0009(11) -0.0005(11) -0.0012(11) C2 0.0179(15) 0.0182(15) 0.0207(13) 0.0009(12) -0.0027(12) -0.0045(11) C3 0.0140(14) 0.0192(15) 0.0194(13) 0.0020(11) 0.0013(11) 0.0017(11) C4 0.0208(15) 0.0165(15) 0.0144(12) 0.0010(11) 0.0012(11) -0.0012(11) C5 0.0144(14) 0.0177(15) 0.0201(13) -0.0014(12) 0.0006(11) -0.0003(11) C6 0.0128(14) 0.0189(16) 0.0171(13) 0.0000(11) 0.0000(11) -0.0019(10) C7 0.0183(15) 0.0172(15) 0.0139(12) 0.0004(11) 0.0006(11) -0.0001(11) C8 0.0150(14) 0.0175(15) 0.0144(12) -0.0024(11) -0.0014(10) -0.0011(10) C9 0.0224(17) 0.0259(18) 0.0171(13) 0.0005(12) 0.0021(12) -0.0034(13) C10 0.0216(17) 0.0264(18) 0.0180(13) -0.0041(13) 0.0048(12) -0.0053(13) C11 0.0178(15) 0.0202(16) 0.0178(13) -0.0018(12) 0.0009(11) -0.0033(11) C12 0.0204(16) 0.0207(17) 0.0268(15) 0.0024(13) 0.0018(13) -0.0023(13) C13 0.0228(17) 0.0156(15) 0.0249(15) -0.0021(12) -0.0049(13) -0.0056(12) C14 0.0227(16) 0.0113(14) 0.0246(14) -0.0015(12) -0.0028(13) -0.0013(11) C15 0.0221(16) 0.0195(16) 0.0216(14) -0.0053(12) -0.0011(12) -0.0047(12) C16 0.0216(17) 0.0248(18) 0.0237(15) -0.0019(13) -0.0061(13) 0.0011(13) C17 0.0198(16) 0.0228(17) 0.0187(13) 0.0000(12) -0.0035(12) -0.0011(12) C18 0.0155(14) 0.0159(15) 0.0180(13) -0.0007(11) -0.0031(11) 0.0029(11) C19 0.0200(15) 0.0183(16) 0.0208(14) 0.0003(12) 0.0010(12) 0.0013(11) C20 0.0208(16) 0.0172(16) 0.0235(15) -0.0030(12) 0.0007(12) 0.0021(12) C21 0.0179(15) 0.0192(16) 0.0195(13) -0.0061(12) 0.0006(12) -0.0016(11) C22 0.035(2) 0.048(3) 0.0307(18) -0.0133(18) 0.0081(16) -0.020(2) C23 0.033(2) 0.040(2) 0.0299(18) -0.0100(17) 0.0172(16) -0.0075(18) O5 0.057(2) 0.055(2) 0.0250(13) -0.0142(14) 0.0088(14) -0.0124(18) O6 0.066(3) 0.106(3) 0.0389(18) -0.025(2) 0.0201(18) -0.043(3) O7 0.193(6) 0.055(3) 0.0340(18) -0.0076(18) -0.029(3) 0.044(3) O8 0.0245(13) 0.0401(16) 0.0233(12) -0.0011(11) 0.0028(10) -0.0053(12) O9 0.0388(18) 0.053(2) 0.055(2) -0.0198(18) -0.0219(16) 0.0198(16) O10 0.0300(16) 0.0298(17) 0.092(3) -0.0256(17) -0.0085(17) 0.0009(13) N3 0.0371(19) 0.043(2) 0.0185(13) -0.0026(13) 0.0033(13) -0.0052(16) N4 0.0269(19) 0.034(2) 0.064(3) -0.0258(19) -0.0113(18) 0.0129(15) C24 0.041(2) 0.048(3) 0.0301(19) -0.0123(19) 0.0074(18) -0.010(2) C25 0.039(2) 0.044(2) 0.0201(16) -0.0100(16) 0.0015(15) -0.0030(19) C26 0.070(4) 0.055(3) 0.0273(19) -0.009(2) -0.014(2) 0.023(3) C27 0.0262(19) 0.032(2) 0.0193(14) -0.0012(14) 0.0030(13) 0.0050(15) C28 0.0211(17) 0.0251(18) 0.0229(15) 0.0005(13) 0.0036(13) 0.0025(13) C29 0.0205(17) 0.0291(19) 0.0214(15) 0.0006(13) -0.0002(13) 0.0012(13) C30 0.0287(19) 0.028(2) 0.0271(17) -0.0028(14) -0.0036(15) 0.0077(15) C31 0.0211(17) 0.0247(18) 0.0391(19) -0.0134(16) -0.0042(15) 0.0069(13) C32 0.028(2) 0.025(2) 0.044(2) -0.0064(17) 0.0063(17) -0.0050(15) C33 0.034(2) 0.029(2) 0.0312(18) 0.0032(15) 0.0058(16) -0.0050(16) O34 0.073(3) 0.060(2) 0.0474(19) 0.0056(18) -0.0121(19) -0.015(2) C34 0.092(5) 0.060(4) 0.075(4) 0.014(3) -0.014(4) 0.001(4) O35 0.052(2) 0.070(3) 0.0379(17) 0.0049(17) 0.0045(16) -0.0100(19) C35 0.103(6) 0.066(4) 0.047(3) -0.003(3) -0.012(3) -0.018(4) O36 0.119(4) 0.074(3) 0.0242(15) 0.0105(17) -0.003(2) -0.033(3) C36 0.071(4) 0.089(5) 0.040(3) 0.005(3) -0.018(3) -0.026(4) O37 0.056(2) 0.060(3) 0.072(3) 0.007(2) -0.010(2) -0.018(2) C37 0.070(4) 0.097(6) 0.068(4) -0.030(4) -0.003(4) -0.021(4) _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 1.429(4) . ? O1 C12 1.456(4) . ? O2 C2 1.371(4) . ? O2 C22 1.440(5) . ? O3 C3 1.367(4) . ? O3 C23 1.442(4) . ? O4 C9 1.236(4) . ? N1 C9 1.354(4) . ? N1 C6 1.429(4) . ? N1 C8 1.488(4) . ? N2 C15 1.495(5) . ? N2 C16 1.511(5) . ? N2 C21 1.539(4) . ? N2 H2 0.8873 . ? C1 C2 1.386(5) . ? C1 C6 1.407(4) . ? C1 H1 0.9500 . ? C2 C3 1.409(5) . ? C3 C4 1.399(5) . ? C4 C5 1.391(4) . ? C4 H4 0.9500 . ? C5 C6 1.389(4) . ? C5 C7 1.509(5) . ? C7 C21 1.526(5) . ? C7 C17 1.546(5) . ? C7 C8 1.574(4) . ? C8 C18 1.536(4) . ? C8 H8 1.0000 . ? C9 C10 1.520(5) . ? C10 C11 1.555(5) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C18 1.534(4) . ? C11 H11 1.0000 . ? C12 C13 1.502(5) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.345(5) . ? C13 H13 0.9500 . ? C14 C15 1.508(5) . ? C14 C19 1.516(5) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 C17 1.522(5) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 C19 1.547(5) . ? C18 H18 1.0000 . ? C19 C20 1.549(5) . ? C19 H19 1.0000 . ? C20 C21 1.514(5) . ? 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 1.269(5) . ? O6 C24 1.217(6) . ? O7 C26 1.401(7) . ? O7 H7 0.8400 . ? O8 C27 1.236(5) . ? O9 N4 1.222(6) . ? O10 N4 1.241(6) . ? N3 C27 1.357(5) . ? N3 C25 1.430(5) . ? N3 H3 0.8800 . ? N4 C31 1.472(5) . ? C24 C25 1.557(6) . ? C25 C26 1.515(7) . ? C25 H25 1.0000 . ? C26 H26A 0.9900 . ? C26 H26B 0.9900 . ? C27 C28 1.503(5) . ? C28 C33 1.383(5) . ? C28 C29 1.389(5) . ? C29 C30 1.392(5) . ? C29 H29 0.9500 . ? C30 C31 1.388(6) . ? C30 H30 0.9500 . ? C31 C32 1.370(6) . ? C32 C33 1.396(6) . ? C32 H32 0.9500 . ? C33 H33 0.9500 . ? O34 C34 1.412(8) . ? O34 H34 0.8400 . ? C34 H34A 0.9800 . ? C34 H34B 0.9800 . ? C34 H34C 0.9800 . ? O35 C35 1.471(8) . ? O35 H35 0.8400 . ? C35 H35A 0.9800 . ? C35 H35B 0.9800 . ? C35 H35C 0.9800 . ? O36 C36 1.448(7) . ? O36 H36 0.8400 . ? C36 H36A 0.9800 . ? C36 H36B 0.9800 . ? C36 H36C 0.9800 . ? O37 C37 1.409(8) . ? O37 H37 0.8400 . ? C37 H37A 0.9800 . ? C37 H37B 0.9800 . ? C37 H37C 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 113.9(3) . . ? C2 O2 C22 116.6(3) . . ? C3 O3 C23 116.7(3) . . ? C9 N1 C6 124.2(3) . . ? C9 N1 C8 119.6(3) . . ? C6 N1 C8 108.6(2) . . ? C15 N2 C16 113.1(3) . . ? C15 N2 C21 114.2(3) . . ? C16 N2 C21 107.2(2) . . ? C15 N2 H2 102.3 . . ? C16 N2 H2 108.8 . . ? C21 N2 H2 111.1 . . ? C2 C1 C6 117.0(3) . . ? C2 C1 H1 121.5 . . ? C6 C1 H1 121.5 . . ? O2 C2 C1 123.0(3) . . ? O2 C2 C3 115.2(3) . . ? C1 C2 C3 121.8(3) . . ? O3 C3 C4 124.9(3) . . ? O3 C3 C2 115.5(3) . . ? C4 C3 C2 119.6(3) . . ? C5 C4 C3 119.5(3) . . ? C5 C4 H4 120.2 . . ? C3 C4 H4 120.2 . . ? C6 C5 C4 119.6(3) . . ? C6 C5 C7 110.6(3) . . ? C4 C5 C7 129.5(3) . . ? C5 C6 C1 122.4(3) . . ? C5 C6 N1 110.8(3) . . ? C1 C6 N1 126.8(3) . . ? C5 C7 C21 115.2(3) . . ? C5 C7 C17 112.2(3) . . ? C21 C7 C17 102.2(2) . . ? C5 C7 C8 102.3(2) . . ? C21 C7 C8 114.3(3) . . ? C17 C7 C8 110.8(3) . . ? N1 C8 C18 105.2(2) . . ? N1 C8 C7 105.1(2) . . ? C18 C8 C7 116.3(3) . . ? N1 C8 H8 110.0 . . ? C18 C8 H8 110.0 . . ? C7 C8 H8 110.0 . . ? O4 C9 N1 122.6(3) . . ? O4 C9 C10 122.4(3) . . ? N1 C9 C10 115.0(3) . . ? C9 C10 C11 115.2(3) . . ? 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 115.3(3) . . ? O1 C11 C10 104.1(3) . . ? C18 C11 C10 110.1(3) . . ? O1 C11 H11 109.0 . . ? C18 C11 H11 109.0 . . ? C10 C11 H11 109.0 . . ? O1 C12 C13 111.2(3) . . ? 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 121.7(3) . . ? C14 C13 H13 119.1 . . ? C12 C13 H13 119.1 . . ? C13 C14 C15 121.0(3) . . ? C13 C14 C19 123.2(3) . . ? C15 C14 C19 115.8(3) . . ? N2 C15 C14 109.5(3) . . ? N2 C15 H15A 109.8 . . ? C14 C15 H15A 109.8 . . ? N2 C15 H15B 109.8 . . ? C14 C15 H15B 109.8 . . ? H15A C15 H15B 108.2 . . ? N2 C16 C17 104.9(3) . . ? 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 103.3(3) . . ? 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 . . ? C11 C18 C8 107.2(3) . . ? C11 C18 C19 118.3(3) . . ? C8 C18 C19 113.2(2) . . ? C11 C18 H18 105.8 . . ? C8 C18 H18 105.8 . . ? C19 C18 H18 105.8 . . ? C14 C19 C18 113.6(3) . . ? C14 C19 C20 109.5(3) . . ? C18 C19 C20 105.9(3) . . ? C14 C19 H19 109.2 . . ? C18 C19 H19 109.2 . . ? C20 C19 H19 109.2 . . ? 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 C7 116.3(3) . . ? C20 C21 N2 110.3(3) . . ? C7 C21 N2 105.4(3) . . ? C20 C21 H21 108.2 . . ? C7 C21 H21 108.2 . . ? N2 C21 H21 108.2 . . ? 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 . . ? C26 O7 H7 109.5 . . ? C27 N3 C25 121.0(4) . . ? C27 N3 H3 119.5 . . ? C25 N3 H3 119.5 . . ? O9 N4 O10 124.5(4) . . ? O9 N4 C31 118.0(4) . . ? O10 N4 C31 117.6(4) . . ? O6 C24 O5 127.0(4) . . ? O6 C24 C25 119.2(4) . . ? O5 C24 C25 113.8(4) . . ? N3 C25 C26 112.8(4) . . ? N3 C25 C24 107.9(4) . . ? C26 C25 C24 112.0(4) . . ? N3 C25 H25 108.0 . . ? C26 C25 H25 108.0 . . ? C24 C25 H25 108.0 . . ? O7 C26 C25 111.7(6) . . ? O7 C26 H26A 109.3 . . ? C25 C26 H26A 109.3 . . ? O7 C26 H26B 109.3 . . ? C25 C26 H26B 109.3 . . ? H26A C26 H26B 107.9 . . ? O8 C27 N3 122.1(4) . . ? O8 C27 C28 120.9(3) . . ? N3 C27 C28 116.9(4) . . ? C33 C28 C29 120.0(4) . . ? C33 C28 C27 123.5(3) . . ? C29 C28 C27 116.5(3) . . ? C28 C29 C30 120.7(4) . . ? C28 C29 H29 119.6 . . ? C30 C29 H29 119.6 . . ? C31 C30 C29 117.5(3) . . ? C31 C30 H30 121.2 . . ? C29 C30 H30 121.2 . . ? C32 C31 C30 123.1(4) . . ? C32 C31 N4 118.7(4) . . ? C30 C31 N4 118.2(4) . . ? C31 C32 C33 118.4(4) . . ? C31 C32 H32 120.8 . . ? C33 C32 H32 120.8 . . ? C28 C33 C32 120.2(4) . . ? C28 C33 H33 119.9 . . ? C32 C33 H33 119.9 . . ? C34 O34 H34 109.5 . . ? O34 C34 H34A 109.5 . . ? O34 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? O34 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? C35 O35 H35 109.5 . . ? 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 . . ? 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 . . ? 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 1.2(5) . . . . ? C22 O2 C2 C3 -179.0(3) . . . . ? C6 C1 C2 O2 179.9(3) . . . . ? C6 C1 C2 C3 0.2(5) . . . . ? C23 O3 C3 C4 3.8(5) . . . . ? C23 O3 C3 C2 -175.0(3) . . . . ? O2 C2 C3 O3 -2.3(4) . . . . ? C1 C2 C3 O3 177.4(3) . . . . ? O2 C2 C3 C4 178.8(3) . . . . ? C1 C2 C3 C4 -1.5(5) . . . . ? O3 C3 C4 C5 -177.3(3) . . . . ? C2 C3 C4 C5 1.6(5) . . . . ? C3 C4 C5 C6 -0.3(5) . . . . ? C3 C4 C5 C7 -173.8(3) . . . . ? C4 C5 C6 C1 -1.0(5) . . . . ? C7 C5 C6 C1 173.6(3) . . . . ? C4 C5 C6 N1 -179.8(3) . . . . ? C7 C5 C6 N1 -5.2(4) . . . . ? C2 C1 C6 C5 1.1(5) . . . . ? C2 C1 C6 N1 179.7(3) . . . . ? C9 N1 C6 C5 -155.0(3) . . . . ? C8 N1 C6 C5 -5.8(4) . . . . ? C9 N1 C6 C1 26.2(5) . . . . ? C8 N1 C6 C1 175.4(3) . . . . ? C6 C5 C7 C21 137.9(3) . . . . ? C4 C5 C7 C21 -48.2(5) . . . . ? C6 C5 C7 C17 -105.7(3) . . . . ? C4 C5 C7 C17 68.2(4) . . . . ? C6 C5 C7 C8 13.2(3) . . . . ? C4 C5 C7 C8 -172.9(3) . . . . ? C9 N1 C8 C18 41.3(4) . . . . ? C6 N1 C8 C18 -109.6(3) . . . . ? C9 N1 C8 C7 164.6(3) . . . . ? C6 N1 C8 C7 13.7(3) . . . . ? C5 C7 C8 N1 -15.8(3) . . . . ? C21 C7 C8 N1 -141.2(3) . . . . ? C17 C7 C8 N1 104.0(3) . . . . ? C5 C7 C8 C18 100.1(3) . . . . ? C21 C7 C8 C18 -25.2(4) . . . . ? C17 C7 C8 C18 -140.0(3) . . . . ? C6 N1 C9 O4 -19.9(6) . . . . ? C8 N1 C9 O4 -166.0(3) . . . . ? C6 N1 C9 C10 161.4(3) . . . . ? C8 N1 C9 C10 15.4(5) . . . . ? O4 C9 C10 C11 137.8(4) . . . . ? N1 C9 C10 C11 -43.5(4) . . . . ? C12 O1 C11 C18 -67.2(4) . . . . ? C12 O1 C11 C10 172.1(2) . . . . ? C9 C10 C11 O1 134.6(3) . . . . ? C9 C10 C11 C18 10.4(4) . . . . ? C11 O1 C12 C13 88.2(3) . . . . ? O1 C12 C13 C14 -65.9(4) . . . . ? C12 C13 C14 C15 178.2(3) . . . . ? C12 C13 C14 C19 -2.1(5) . . . . ? C16 N2 C15 C14 77.4(3) . . . . ? C21 N2 C15 C14 -45.6(4) . . . . ? C13 C14 C15 N2 -126.3(3) . . . . ? C19 C14 C15 N2 53.9(4) . . . . ? C15 N2 C16 C17 -142.0(3) . . . . ? C21 N2 C16 C17 -15.2(3) . . . . ? N2 C16 C17 C7 35.2(3) . . . . ? C5 C7 C17 C16 -165.6(3) . . . . ? C21 C7 C17 C16 -41.5(3) . . . . ? C8 C7 C17 C16 80.7(3) . . . . ? O1 C11 C18 C8 -72.6(3) . . . . ? C10 C11 C18 C8 44.8(3) . . . . ? O1 C11 C18 C19 56.7(4) . . . . ? C10 C11 C18 C19 174.1(3) . . . . ? N1 C8 C18 C11 -72.0(3) . . . . ? C7 C8 C18 C11 172.2(3) . . . . ? N1 C8 C18 C19 155.8(3) . . . . ? C7 C8 C18 C19 40.0(4) . . . . ? C13 C14 C19 C18 58.8(4) . . . . ? C15 C14 C19 C18 -121.5(3) . . . . ? C13 C14 C19 C20 176.9(3) . . . . ? C15 C14 C19 C20 -3.3(4) . . . . ? C11 C18 C19 C14 -67.1(4) . . . . ? C8 C18 C19 C14 59.4(4) . . . . ? C11 C18 C19 C20 172.7(3) . . . . ? C8 C18 C19 C20 -60.9(3) . . . . ? C14 C19 C20 C21 -54.5(3) . . . . ? C18 C19 C20 C21 68.4(3) . . . . ? C19 C20 C21 C7 -57.4(4) . . . . ? C19 C20 C21 N2 62.4(3) . . . . ? C5 C7 C21 C20 -83.5(4) . . . . ? C17 C7 C21 C20 154.5(3) . . . . ? C8 C7 C21 C20 34.7(4) . . . . ? C5 C7 C21 N2 153.9(3) . . . . ? C17 C7 C21 N2 32.0(3) . . . . ? C8 C7 C21 N2 -87.9(3) . . . . ? C15 N2 C21 C20 -11.0(4) . . . . ? C16 N2 C21 C20 -137.1(3) . . . . ? C15 N2 C21 C7 115.3(3) . . . . ? C16 N2 C21 C7 -10.8(3) . . . . ? C27 N3 C25 C26 79.8(5) . . . . ? C27 N3 C25 C24 -155.9(4) . . . . ? O6 C24 C25 N3 -1.8(7) . . . . ? O5 C24 C25 N3 178.6(4) . . . . ? O6 C24 C25 C26 123.0(6) . . . . ? O5 C24 C25 C26 -56.6(6) . . . . ? N3 C25 C26 O7 66.6(5) . . . . ? C24 C25 C26 O7 -55.5(5) . . . . ? C25 N3 C27 O8 -1.9(6) . . . . ? C25 N3 C27 C28 174.9(4) . . . . ? O8 C27 C28 C33 -155.2(4) . . . . ? N3 C27 C28 C33 28.0(6) . . . . ? O8 C27 C28 C29 25.6(5) . . . . ? N3 C27 C28 C29 -151.3(4) . . . . ? C33 C28 C29 C30 -3.1(6) . . . . ? C27 C28 C29 C30 176.2(3) . . . . ? C28 C29 C30 C31 0.5(6) . . . . ? C29 C30 C31 C32 1.8(6) . . . . ? C29 C30 C31 N4 -175.8(3) . . . . ? O9 N4 C31 C32 178.9(4) . . . . ? O10 N4 C31 C32 -2.3(5) . . . . ? O9 N4 C31 C30 -3.4(5) . . . . ? O10 N4 C31 C30 175.4(3) . . . . ? C30 C31 C32 C33 -1.4(6) . . . . ? N4 C31 C32 C33 176.2(4) . . . . ? C29 C28 C33 C32 3.5(6) . . . . ? C27 C28 C33 C32 -175.8(4) . . . . ? C31 C32 C33 C28 -1.3(6) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2 O5 0.89 1.82 2.653(4) 154.9 . O7 H7 O36 0.84 1.91 2.735(6) 167.4 2_575 O34 H34 O5 0.84 1.88 2.717(6) 175.7 . O35 H35 O6 0.84 1.94 2.780(6) 174.9 . O36 H36 O4 0.84 1.82 2.650(4) 167.4 . O37 H37 O8 0.84 1.95 2.786(5) 174.5 . _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 36.00 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 0.417 _refine_diff_density_min -0.369 _refine_diff_density_rms 0.080 # start Validation Reply Form _vrf_PLAT222_6 ; PROBLEM: Large Non-Solvent H Ueq(max)/Ueq(min) ... 5.04 Ratio RESPONSE: It can be a result of unsolved disorder of hydroxyl group of the serine derivative - a little elongated termal ellipsoid for the O7 atom ; # end Validation Reply Form #====== end of cif # Attachment 'bialonska2.cif' data_7 _database_code_depnum_ccdc_archive 'CCDC 758148' #TrackingRef 'bialonska2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; brucinium N-(4-nitrobenzoyl)-D-serinate 3.25-hydrate ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C23 H27 N2 O4, C10 H9 N2 O6, 3.25(H2 O)' _chemical_formula_sum 'C33 H42.50 N4 O13.25' _chemical_formula_weight 707.21 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 7.850(2) _cell_length_b 12.477(2) _cell_length_c 33.105(4) _cell_angle_alpha 90.00 _cell_angle_beta 92.58(3) _cell_angle_gamma 90.00 _cell_volume 3239.2(11) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6504 _cell_measurement_theta_min 2.82 _cell_measurement_theta_max 28.59 _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.450 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1498 _exptl_absorpt_coefficient_mu 0.113 _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 25150 _diffrn_reflns_av_R_equivalents 0.0851 _diffrn_reflns_av_sigmaI/netI 0.1558 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -42 _diffrn_reflns_limit_l_max 35 _diffrn_reflns_theta_min 2.82 _diffrn_reflns_theta_max 27.00 _reflns_number_total 7374 _reflns_number_gt 3859 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET) (compiled May 8 2007,13:10:02) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET) (compiled May 8 2007,13:10:02) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET) (compiled May 8 2007,13:10:02) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0402P)^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 7374 _refine_ls_number_parameters 938 _refine_ls_number_restraints 45 _refine_ls_R_factor_all 0.1103 _refine_ls_R_factor_gt 0.0467 _refine_ls_wR_factor_ref 0.0964 _refine_ls_wR_factor_gt 0.0828 _refine_ls_goodness_of_fit_ref 0.895 _refine_ls_restrained_S_all 0.892 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.1627(4) 0.9368(2) 0.43492(9) 0.0253(8) Uani 1 1 d . . . O2 O 0.2820(4) 0.3570(3) 0.57856(9) 0.0285(9) Uani 1 1 d . . . O3 O 0.2812(4) 0.2470(3) 0.51252(9) 0.0304(9) Uani 1 1 d . . . O4 O 0.2698(5) 0.7540(3) 0.55670(10) 0.0346(9) Uani 1 1 d . . . N1 N 0.1694(5) 0.6828(3) 0.49712(11) 0.0232(10) Uani 1 1 d . . . N2 N 0.0629(5) 0.5983(3) 0.36312(11) 0.0267(10) Uani 1 1 d . . . H24 H 0.0416 0.5411 0.3456 0.032 Uiso 1 1 calc R . . C1 C 0.2288(6) 0.5241(4) 0.54316(14) 0.0212(12) Uani 1 1 d . . . H1 H 0.2341 0.5650 0.5674 0.025 Uiso 1 1 calc R . . C2 C 0.2541(6) 0.4137(4) 0.54355(14) 0.0227(12) Uani 1 1 d U . . C3 C 0.2470(6) 0.3548(4) 0.50783(14) 0.0233(12) Uani 1 1 d . . . C4 C 0.2098(6) 0.4029(4) 0.47086(15) 0.0277(13) Uani 1 1 d . . . H4 H 0.2026 0.3621 0.4466 0.033 Uiso 1 1 calc R . . C5 C 0.1830(6) 0.5144(4) 0.47041(14) 0.0231(12) Uani 1 1 d . . . C6 C 0.1957(6) 0.5719(4) 0.50574(14) 0.0211(12) Uani 1 1 d . . . C7 C 0.1179(6) 0.5826(4) 0.43574(13) 0.0218(12) Uani 1 1 d . . . C8 C 0.1477(6) 0.6981(4) 0.45294(13) 0.0223(12) Uani 1 1 d . . . H8 H 0.0436 0.7424 0.4468 0.027 Uiso 1 1 calc R . . C9 C 0.2296(6) 0.7651(4) 0.52071(15) 0.0255(12) Uani 1 1 d . . . C10 C 0.2437(7) 0.8723(4) 0.49989(14) 0.0271(13) Uani 1 1 d . . . H10A H 0.3305 0.9151 0.5154 0.033 Uiso 1 1 calc R . . H10B H 0.1333 0.9097 0.5019 0.033 Uiso 1 1 calc R . . C11 C 0.2899(6) 0.8737(4) 0.45523(14) 0.0260(12) Uani 1 1 d . . . H11 H 0.4029 0.9097 0.4530 0.031 Uiso 1 1 calc R . . C12 C 0.1963(7) 0.9627(4) 0.39403(14) 0.0286(13) Uani 1 1 d . . . H12A H 0.3208 0.9716 0.3916 0.034 Uiso 1 1 calc R . . H12B H 0.1410 1.0318 0.3868 0.034 Uiso 1 1 calc R . . C13 C 0.1324(6) 0.8776(4) 0.36457(13) 0.0250(12) Uani 1 1 d . . . H13 H 0.0481 0.8960 0.3443 0.030 Uiso 1 1 calc R . . C14 C 0.1910(6) 0.7784(4) 0.36638(13) 0.0232(12) Uani 1 1 d . . . C15 C 0.1166(6) 0.6927(4) 0.33857(13) 0.0249(12) Uani 1 1 d . . . H15A H 0.0169 0.7217 0.3228 0.030 Uiso 1 1 calc R . . H15B H 0.2027 0.6699 0.3194 0.030 Uiso 1 1 calc R . . C16 C -0.0984(6) 0.6215(4) 0.38470(13) 0.0273(12) Uani 1 1 d . . . H16A H -0.1996 0.5925 0.3695 0.033 Uiso 1 1 calc R . . H16B H -0.1137 0.6995 0.3886 0.033 Uiso 1 1 calc R . . C17 C -0.0692(6) 0.5643(4) 0.42505(13) 0.0279(13) Uani 1 1 d . . . H17A H -0.1413 0.5954 0.4458 0.033 Uiso 1 1 calc R . . H17B H -0.0946 0.4869 0.4224 0.033 Uiso 1 1 calc R . . C18 C 0.3030(6) 0.7583(4) 0.43983(13) 0.0232(12) Uani 1 1 d . . . H18 H 0.4032 0.7257 0.4550 0.028 Uiso 1 1 calc R . . C19 C 0.3345(6) 0.7436(4) 0.39500(13) 0.0248(12) Uani 1 1 d . . . H19 H 0.4400 0.7837 0.3884 0.030 Uiso 1 1 calc R . . C20 C 0.3661(6) 0.6213(4) 0.38904(15) 0.0281(13) Uani 1 1 d . . . H20A H 0.4056 0.6075 0.3615 0.034 Uiso 1 1 calc R . . H20B H 0.4546 0.5955 0.4090 0.034 Uiso 1 1 calc R . . C21 C 0.1979(6) 0.5634(4) 0.39500(13) 0.0244(12) Uani 1 1 d . . . H21 H 0.2174 0.4847 0.3919 0.029 Uiso 1 1 calc R . . C22 C 0.2891(6) 0.4170(4) 0.61520(13) 0.0277(13) Uani 1 1 d . . . H22A H 0.3069 0.3682 0.6382 0.042 Uiso 1 1 calc R . . H22B H 0.1817 0.4559 0.6178 0.042 Uiso 1 1 calc R . . H22C H 0.3837 0.4682 0.6149 0.042 Uiso 1 1 calc R . . C23 C 0.2808(7) 0.1852(4) 0.47637(14) 0.0339(14) Uani 1 1 d . . . H23A H 0.3077 0.1104 0.4831 0.051 Uiso 1 1 calc R . . H23B H 0.3666 0.2135 0.4586 0.051 Uiso 1 1 calc R . . H23C H 0.1679 0.1890 0.4626 0.051 Uiso 1 1 calc R . . O1A O 0.2706(4) 0.3694(2) 0.05388(9) 0.0264(8) Uani 1 1 d . . . O2A O 0.1333(4) 0.9487(2) -0.08524(8) 0.0214(8) Uani 1 1 d . . . O3A O 0.1987(4) 1.0589(2) -0.01992(9) 0.0218(8) Uani 1 1 d . . . O4A O 0.1580(4) 0.5496(3) -0.06672(10) 0.0264(8) Uani 1 1 d . . . N1A N 0.1701(5) 0.6169(3) -0.00298(11) 0.0175(9) Uani 1 1 d . . . N2A N 0.2689(5) 0.6975(3) 0.13151(11) 0.0252(10) Uani 1 1 d . . . H24A H 0.2718 0.7544 0.1497 0.030 Uiso 1 1 calc R . . C1A C 0.1454(5) 0.7786(4) -0.04954(13) 0.0185(11) Uani 1 1 d . . . H1A H 0.1246 0.7377 -0.0735 0.022 Uiso 1 1 calc R . . C2A C 0.1530(5) 0.8901(4) -0.05051(14) 0.0177(11) Uani 1 1 d U . . C3A C 0.1865(6) 0.9492(4) -0.01493(13) 0.0175(11) Uani 1 1 d . . . C4A C 0.2073(6) 0.8983(4) 0.02183(14) 0.0211(12) Uani 1 1 d . . . H4A H 0.2276 0.9387 0.0459 0.025 Uiso 1 1 calc R . . C5A C 0.1982(6) 0.7867(3) 0.02333(14) 0.0176(11) Uani 1 1 d . . . C6A C 0.1697(6) 0.7299(4) -0.01183(14) 0.0183(11) Uani 1 1 d . . . C7A C 0.2029(6) 0.7143(4) 0.05946(13) 0.0194(11) Uani 1 1 d . . . C8A C 0.2151(6) 0.6012(4) 0.04028(12) 0.0184(11) Uani 1 1 d . . . H8A H 0.1300 0.5525 0.0524 0.022 Uiso 1 1 calc R . . C9A C 0.1926(6) 0.5388(4) -0.03038(16) 0.0228(12) Uani 1 1 d . . . C10A C 0.2578(7) 0.4318(4) -0.01330(15) 0.0285(13) Uani 1 1 d . . . H10C H 0.3281 0.3980 -0.0339 0.034 Uiso 1 1 calc R . . H10D H 0.1578 0.3847 -0.0100 0.034 Uiso 1 1 calc R . . C11A C 0.3629(6) 0.4326(3) 0.02694(14) 0.0218(12) Uani 1 1 d . . . H11A H 0.4761 0.3983 0.0229 0.026 Uiso 1 1 calc R . . C12A C 0.3620(7) 0.3415(4) 0.09051(14) 0.0316(13) Uani 1 1 d . . . H12C H 0.4837 0.3311 0.0849 0.038 Uiso 1 1 calc R . . H12D H 0.3176 0.2726 0.1005 0.038 Uiso 1 1 calc R . . C13A C 0.3483(6) 0.4248(4) 0.12281(14) 0.0262(13) Uani 1 1 d . . . H13A H 0.2992 0.4043 0.1473 0.031 Uiso 1 1 calc R . . C14A C 0.4006(6) 0.5254(4) 0.11931(14) 0.0246(12) Uani 1 1 d . . . C15A C 0.3698(7) 0.6078(4) 0.15094(13) 0.0266(12) Uani 1 1 d . . . H15C H 0.4799 0.6352 0.1625 0.032 Uiso 1 1 calc R . . H15D H 0.3059 0.5757 0.1730 0.032 Uiso 1 1 calc R . . C16A C 0.0856(6) 0.6695(4) 0.12303(13) 0.0233(12) Uani 1 1 d . . . H16C H 0.0141 0.6962 0.1448 0.028 Uiso 1 1 calc R . . H16D H 0.0706 0.5910 0.1205 0.028 Uiso 1 1 calc R . . C17A C 0.0397(6) 0.7254(4) 0.08321(13) 0.0228(12) Uani 1 1 d . . . H17C H 0.0112 0.8017 0.0876 0.027 Uiso 1 1 calc R . . H17D H -0.0581 0.6898 0.0688 0.027 Uiso 1 1 calc R . . C18A C 0.3910(6) 0.5475(4) 0.04213(13) 0.0185(11) Uani 1 1 d . . . H18A H 0.4586 0.5844 0.0213 0.022 Uiso 1 1 calc R . . C19A C 0.4877(6) 0.5660(4) 0.08270(13) 0.0218(11) Uani 1 1 d . . . H19A H 0.6018 0.5307 0.0818 0.026 Uiso 1 1 calc R . . C20A C 0.5147(6) 0.6888(4) 0.08619(14) 0.0253(12) Uani 1 1 d . . . H20C H 0.5952 0.7056 0.1092 0.030 Uiso 1 1 calc R . . H20D H 0.5622 0.7172 0.0611 0.030 Uiso 1 1 calc R . . C21A C 0.3430(6) 0.7381(4) 0.09272(13) 0.0212(11) Uani 1 1 d . . . H21A H 0.3575 0.8176 0.0949 0.025 Uiso 1 1 calc R . . C22A C 0.1204(6) 0.8902(4) -0.12233(13) 0.0277(13) Uani 1 1 d . . . H22D H 0.1051 0.9404 -0.1450 0.042 Uiso 1 1 calc R . . H22E H 0.0224 0.8416 -0.1220 0.042 Uiso 1 1 calc R . . H22F H 0.2248 0.8486 -0.1254 0.042 Uiso 1 1 calc R . . C23A C 0.2360(7) 1.1201(4) 0.01628(13) 0.0260(12) Uani 1 1 d . . . H23D H 0.2419 1.1964 0.0095 0.039 Uiso 1 1 calc R . . H23E H 0.3456 1.0969 0.0287 0.039 Uiso 1 1 calc R . . H23F H 0.1458 1.1086 0.0354 0.039 Uiso 1 1 calc R . . O5 O -0.0304(5) 0.4533(3) 0.30572(10) 0.0343(9) Uani 1 1 d . . . O6 O -0.3055(5) 0.4853(3) 0.31676(10) 0.0410(10) Uani 1 1 d . . . O8 O -0.2697(5) 0.2057(3) 0.21236(11) 0.0496(11) Uani 1 1 d . B . O9 O 0.3875(4) 0.0168(3) 0.10227(10) 0.0306(9) Uani 1 1 d . . . O10 O 0.5614(4) 0.1261(3) 0.13382(10) 0.0344(9) Uani 1 1 d . . . N3 N -0.1031(5) 0.3348(3) 0.24045(11) 0.0232(10) Uani 1 1 d . B . H3 H 0.0015 0.3588 0.2448 0.028 Uiso 1 1 calc R . . N4 N 0.4205(6) 0.0850(3) 0.12862(12) 0.0254(10) Uani 1 1 d . B . C24 C -0.1868(7) 0.4475(4) 0.29666(15) 0.0275(12) Uani 1 1 d . B . C25 C -0.2439(6) 0.3912(4) 0.25795(14) 0.0268(12) Uani 1 1 d D . . H25 H -0.3227 0.3334 0.2666 0.032 Uiso 1 1 calc R A 1 C26 C -0.3470(14) 0.4534(10) 0.2246(4) 0.032(3) Uani 0.50 1 d PDU B 1 H26A H -0.4029 0.4016 0.2057 0.038 Uiso 0.50 1 calc PR B 1 H26B H -0.4374 0.4955 0.2372 0.038 Uiso 0.50 1 calc PR B 1 O7 O -0.2417(11) 0.5241(6) 0.2026(2) 0.0323(18) Uani 0.50 1 d PDU B 1 H7 H -0.1800 0.5753 0.2084 0.049 Uiso 0.50 1 d P C 1 C261 C -0.3047(13) 0.4815(10) 0.2288(5) 0.033(3) Uani 0.50 1 d PDU B 2 H261 H -0.3420 0.4496 0.2024 0.040 Uiso 0.50 1 calc PR B 2 H262 H -0.4040 0.5181 0.2399 0.040 Uiso 0.50 1 calc PR B 2 O71 O -0.1735(10) 0.5585(6) 0.2225(2) 0.0359(19) Uani 0.50 1 d PDU B 2 H71 H -0.0803 0.5409 0.2343 0.054 Uiso 0.50 1 d P D 2 C27 C -0.1294(7) 0.2465(4) 0.21766(14) 0.0289(13) Uani 1 1 d . . . C28 C 0.0239(7) 0.2000(4) 0.19791(14) 0.0249(12) Uani 1 1 d . B . C29 C -0.0125(6) 0.1317(4) 0.16491(13) 0.0231(12) Uani 1 1 d . . . H29 H -0.1274 0.1138 0.1575 0.028 Uiso 1 1 calc R B . C30 C 0.1185(6) 0.0908(4) 0.14329(14) 0.0248(12) Uani 1 1 d . B . H30 H 0.0956 0.0433 0.1213 0.030 Uiso 1 1 calc R . . C31 C 0.2822(6) 0.1199(4) 0.15414(13) 0.0191(11) Uani 1 1 d . . . C32 C 0.3250(6) 0.1841(4) 0.18758(13) 0.0222(12) Uani 1 1 d . B . H32 H 0.4405 0.2001 0.1950 0.027 Uiso 1 1 calc R . . C33 C 0.1914(6) 0.2239(4) 0.20967(14) 0.0240(12) Uani 1 1 d . . . H33 H 0.2154 0.2673 0.2328 0.029 Uiso 1 1 calc R B . O5A O 0.2330(4) 0.8550(3) 0.18103(9) 0.0291(9) Uani 1 1 d . . . O6A O 0.5089(4) 0.9027(3) 0.18198(9) 0.0329(9) Uani 1 1 d . . . O7A O 0.4049(5) 0.7432(3) 0.25857(11) 0.0447(10) Uani 1 1 d . . . H7A H 0.3495 0.6812 0.2569 0.067 Uiso 1 1 d . . . O8A O 0.3881(4) 1.0376(3) 0.31306(10) 0.0317(9) Uani 1 1 d . . . O9A O 1.1256(5) 1.2921(3) 0.37712(11) 0.0588(13) Uani 1 1 d . . . O10A O 1.2368(5) 1.2570(3) 0.31940(11) 0.0407(10) Uani 1 1 d . . . N3A N 0.5077(5) 0.9781(3) 0.25675(11) 0.0262(10) Uani 1 1 d . . . H3A H 0.6003 0.9735 0.2428 0.031 Uiso 1 1 calc R . . N4A N 1.1213(6) 1.2500(4) 0.34366(15) 0.0391(12) Uani 1 1 d . . . C24A C 0.3687(7) 0.8943(4) 0.19755(15) 0.0256(12) Uani 1 1 d . . . C25A C 0.3498(6) 0.9283(4) 0.24102(14) 0.0254(12) Uani 1 1 d . . . H25A H 0.2574 0.9834 0.2414 0.030 Uiso 1 1 calc R . . C26A C 0.2962(7) 0.8341(4) 0.26628(15) 0.0319(13) Uani 1 1 d . . . H26C H 0.3058 0.8531 0.2953 0.038 Uiso 1 1 calc R . . H26D H 0.1758 0.8155 0.2593 0.038 Uiso 1 1 calc R . . C27A C 0.5136(7) 1.0307(4) 0.29207(15) 0.0236(12) Uani 1 1 d . . . C28A C 0.6783(6) 1.0835(4) 0.30513(14) 0.0243(12) Uani 1 1 d . . . C29A C 0.6720(7) 1.1626(4) 0.33494(14) 0.0276(13) Uani 1 1 d . . . H29A H 0.5660 1.1804 0.3460 0.033 Uiso 1 1 calc R . . C30A C 0.8172(7) 1.2144(4) 0.34831(15) 0.0309(13) Uani 1 1 d . . . H30A H 0.8138 1.2673 0.3689 0.037 Uiso 1 1 calc R . . C31A C 0.9680(7) 1.1885(4) 0.33134(15) 0.0299(13) Uani 1 1 d . . . C32A C 0.9811(7) 1.1113(4) 0.30257(15) 0.0284(12) Uani 1 1 d . . . H32A H 1.0882 1.0945 0.2919 0.034 Uiso 1 1 calc R . . C33A C 0.8341(7) 1.0579(4) 0.28917(15) 0.0315(13) Uani 1 1 d . . . H33A H 0.8399 1.0038 0.2691 0.038 Uiso 1 1 calc R . . O1W O -0.4473(7) 0.4073(5) 0.39639(17) 0.114(2) Uani 1 1 d . . . H11W H -0.3904 0.3590 0.4113 0.171 Uiso 1 1 d . . . H12W H -0.4057 0.4287 0.3747 0.171 Uiso 1 1 d . . . O2W O 0.3524(4) 0.4724(3) 0.30332(10) 0.0374(9) Uani 1 1 d . . . H21W H 0.4611 0.4732 0.3017 0.056 Uiso 1 1 d . . . H22W H 0.3204 0.4076 0.3059 0.056 Uiso 1 1 d . . . O3W O 0.1958(4) 0.5720(3) 0.23755(10) 0.0434(10) Uani 1 1 d . . . H31W H 0.1059 0.5976 0.2476 0.065 Uiso 1 1 d . . . H32W H 0.2385 0.5256 0.2543 0.065 Uiso 1 1 d . . . O4W O -0.0923(4) 0.8857(3) 0.20700(10) 0.0365(9) Uani 1 1 d . . . H41W H 0.0167 0.8842 0.2049 0.055 Uiso 1 1 d . . . H42W H -0.1460 0.8756 0.1841 0.055 Uiso 1 1 d . . . O5W O 0.7545(4) 0.8913(2) 0.12534(10) 0.0304(9) Uani 1 1 d . . . H51W H 0.6515 0.8995 0.1328 0.046 Uiso 1 1 d . . . H52W H 0.7763 0.9437 0.1093 0.046 Uiso 1 1 d . . . O6W O -0.3356(9) 0.7175(5) 0.30850(18) 0.0357(19) Uani 0.50 1 d P E 1 H61W H -0.3254 0.6450 0.3113 0.054 Uiso 0.50 1 d P F 1 H62W H -0.4319 0.7377 0.2978 0.054 Uiso 0.50 1 d P G 1 O7W O -0.1165(9) 0.6945(6) 0.2451(2) 0.0347(18) Uani 0.50 1 d P H 1 H71W H -0.1812 0.7014 0.2642 0.052 Uiso 0.50 1 d P I 1 H72W H -0.1071 0.7568 0.2325 0.052 Uiso 0.50 1 d P J 1 O61W O -0.2209(10) 0.7404(6) 0.2633(2) 0.042(2) Uani 0.50 1 d P K 2 H63W H -0.3487 0.7212 0.2702 0.063 Uiso 0.50 1 d P L 2 H64W H -0.1821 0.7831 0.2460 0.063 Uiso 0.50 1 d P M 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 0.033(2) 0.0207(19) 0.022(2) 0.0027(15) 0.0026(16) 0.0017(17) O2 0.036(2) 0.026(2) 0.024(2) 0.0027(16) 0.0005(16) 0.0004(17) O3 0.044(2) 0.0197(19) 0.027(2) 0.0021(17) 0.0001(17) 0.0028(18) O4 0.057(3) 0.025(2) 0.022(2) -0.0054(17) -0.0007(18) -0.0050(19) N1 0.030(3) 0.021(2) 0.019(2) -0.0033(19) 0.0007(19) -0.002(2) N2 0.039(3) 0.018(2) 0.023(2) -0.0028(19) -0.002(2) 0.000(2) C1 0.017(3) 0.024(3) 0.022(3) -0.001(2) 0.003(2) -0.001(2) C2 0.023(3) 0.029(3) 0.016(3) 0.004(2) 0.000(2) 0.002(2) C3 0.023(3) 0.015(3) 0.032(3) 0.002(2) 0.002(2) -0.001(2) C4 0.031(3) 0.019(3) 0.034(3) -0.003(2) 0.008(3) -0.005(2) C5 0.025(3) 0.023(3) 0.022(3) -0.001(2) -0.001(2) -0.001(2) C6 0.027(3) 0.013(3) 0.024(3) 0.000(2) 0.005(2) -0.002(2) C7 0.033(3) 0.014(3) 0.019(3) -0.001(2) 0.004(2) -0.006(2) C8 0.028(3) 0.019(3) 0.021(3) 0.000(2) 0.004(2) 0.005(2) C9 0.028(3) 0.026(3) 0.023(3) -0.006(3) 0.008(2) 0.001(3) C10 0.030(3) 0.025(3) 0.027(3) 0.001(2) 0.004(2) -0.008(2) C11 0.026(3) 0.023(3) 0.029(3) -0.004(2) 0.001(2) 0.000(2) C12 0.035(3) 0.020(3) 0.031(3) 0.001(3) 0.003(3) 0.000(3) C13 0.037(3) 0.022(3) 0.017(3) 0.002(2) 0.004(2) 0.002(3) C14 0.027(3) 0.021(3) 0.023(3) 0.003(2) 0.008(2) -0.004(2) C15 0.034(3) 0.021(3) 0.021(3) 0.004(2) 0.006(2) -0.003(2) C16 0.030(3) 0.026(3) 0.026(3) -0.003(2) 0.003(2) -0.005(3) C17 0.042(4) 0.019(3) 0.022(3) 0.003(2) 0.000(3) -0.003(3) C18 0.024(3) 0.018(3) 0.028(3) -0.001(2) 0.005(2) 0.003(2) C19 0.025(3) 0.023(3) 0.027(3) -0.002(2) 0.001(2) -0.004(2) C20 0.034(3) 0.018(3) 0.033(3) -0.007(2) 0.006(3) 0.002(3) C21 0.033(3) 0.017(3) 0.023(3) 0.001(2) -0.002(2) 0.002(2) C22 0.032(3) 0.029(3) 0.022(3) 0.004(2) 0.000(2) 0.001(3) C23 0.048(4) 0.018(3) 0.035(3) -0.007(3) 0.003(3) 0.002(3) O1A 0.032(2) 0.020(2) 0.028(2) 0.0001(16) -0.0005(17) -0.0053(16) O2A 0.027(2) 0.0166(18) 0.0209(19) 0.0018(15) 0.0024(15) -0.0004(16) O3A 0.029(2) 0.0122(18) 0.0245(19) -0.0049(15) -0.0009(16) -0.0012(16) O4A 0.035(2) 0.0211(19) 0.022(2) -0.0028(15) -0.0016(17) 0.0038(17) N1A 0.017(2) 0.009(2) 0.026(2) -0.0002(18) 0.0036(18) 0.0039(18) N2A 0.030(3) 0.020(2) 0.025(2) -0.0007(19) 0.002(2) 0.000(2) C1A 0.014(3) 0.019(3) 0.022(3) -0.003(2) -0.002(2) 0.003(2) C2A 0.010(3) 0.016(3) 0.027(3) 0.003(2) 0.005(2) 0.002(2) C3A 0.015(3) 0.013(3) 0.024(3) -0.001(2) 0.000(2) -0.004(2) C4A 0.024(3) 0.021(3) 0.018(3) -0.003(2) -0.001(2) 0.004(2) C5A 0.020(3) 0.010(3) 0.022(3) 0.000(2) -0.004(2) 0.003(2) C6A 0.012(3) 0.015(3) 0.028(3) 0.001(2) 0.004(2) 0.002(2) C7A 0.017(3) 0.021(3) 0.021(3) -0.004(2) 0.003(2) 0.003(2) C8A 0.019(3) 0.015(3) 0.021(3) 0.000(2) 0.002(2) 0.001(2) C9A 0.017(3) 0.016(3) 0.035(3) -0.003(2) 0.003(2) -0.004(2) C10A 0.036(3) 0.015(3) 0.034(3) -0.008(2) -0.002(3) 0.008(2) C11A 0.023(3) 0.015(3) 0.028(3) -0.002(2) 0.003(2) 0.004(2) C12A 0.038(4) 0.022(3) 0.034(3) 0.009(3) 0.000(3) -0.002(3) C13A 0.034(3) 0.024(3) 0.021(3) 0.004(2) 0.005(2) 0.003(3) C14A 0.021(3) 0.023(3) 0.030(3) 0.000(2) -0.003(2) 0.000(2) C15A 0.037(3) 0.024(3) 0.019(3) 0.005(2) 0.003(2) 0.001(3) C16A 0.019(3) 0.022(3) 0.030(3) -0.001(2) 0.002(2) 0.002(2) C17A 0.027(3) 0.020(3) 0.022(3) -0.004(2) 0.003(2) 0.002(2) C18A 0.021(3) 0.014(3) 0.021(3) 0.001(2) 0.003(2) -0.001(2) C19A 0.021(3) 0.016(3) 0.027(3) 0.000(2) -0.002(2) 0.003(2) C20A 0.032(3) 0.017(3) 0.027(3) -0.002(2) -0.002(2) -0.002(2) C21A 0.026(3) 0.015(3) 0.023(3) 0.004(2) 0.010(2) -0.002(2) C22A 0.036(3) 0.020(3) 0.027(3) 0.002(2) 0.005(3) 0.002(3) C23A 0.035(3) 0.015(3) 0.027(3) -0.004(2) -0.002(2) -0.002(2) O5 0.026(2) 0.031(2) 0.046(2) -0.0180(18) 0.0009(18) 0.0009(18) O6 0.032(2) 0.040(2) 0.051(2) -0.026(2) 0.0056(19) -0.0042(19) O8 0.028(2) 0.060(3) 0.060(3) -0.034(2) -0.003(2) -0.001(2) O9 0.033(2) 0.029(2) 0.030(2) -0.0058(17) -0.0025(17) 0.0029(17) O10 0.019(2) 0.038(2) 0.046(2) -0.0067(18) -0.0008(18) 0.0041(19) N3 0.023(3) 0.019(2) 0.028(2) -0.0054(19) 0.0003(19) -0.0002(19) N4 0.034(3) 0.019(2) 0.022(2) -0.003(2) -0.007(2) 0.011(2) C24 0.024(3) 0.024(3) 0.035(3) -0.006(3) 0.006(3) -0.001(3) C25 0.027(3) 0.025(3) 0.028(3) 0.001(2) 0.003(2) 0.005(2) C26 0.041(6) 0.016(6) 0.039(6) 0.000(5) 0.007(5) -0.002(5) O7 0.038(5) 0.025(4) 0.034(5) -0.001(3) -0.002(3) -0.005(3) C261 0.036(6) 0.024(6) 0.039(5) 0.003(5) 0.004(5) 0.003(5) O71 0.028(5) 0.037(5) 0.042(5) 0.015(4) 0.002(4) 0.000(4) C27 0.032(4) 0.026(3) 0.029(3) -0.003(3) -0.003(3) 0.000(3) C28 0.035(3) 0.020(3) 0.020(3) 0.001(2) 0.002(2) 0.005(3) C29 0.028(3) 0.017(3) 0.025(3) 0.001(2) 0.000(2) -0.001(2) C30 0.030(3) 0.014(3) 0.030(3) -0.003(2) -0.006(3) 0.003(2) C31 0.023(3) 0.015(3) 0.019(3) 0.004(2) -0.002(2) 0.006(2) C32 0.025(3) 0.021(3) 0.020(3) 0.004(2) -0.004(2) -0.002(2) C33 0.029(3) 0.021(3) 0.022(3) -0.003(2) -0.001(2) 0.002(2) O5A 0.035(2) 0.026(2) 0.027(2) -0.0055(16) 0.0056(17) -0.0010(17) O6A 0.033(2) 0.037(2) 0.030(2) 0.0021(17) 0.0105(19) 0.0037(19) O7A 0.057(3) 0.014(2) 0.064(3) 0.0105(19) 0.013(2) 0.002(2) O8A 0.033(2) 0.031(2) 0.032(2) -0.0057(17) 0.0094(18) -0.0004(18) O9A 0.073(3) 0.072(3) 0.031(2) -0.006(2) -0.009(2) -0.034(3) O10A 0.035(2) 0.025(2) 0.063(3) 0.000(2) 0.007(2) -0.0009(19) N3A 0.021(2) 0.029(3) 0.028(2) -0.002(2) 0.0035(19) 0.001(2) N4A 0.043(3) 0.036(3) 0.038(3) 0.003(3) -0.007(3) -0.005(3) C24A 0.036(4) 0.019(3) 0.022(3) 0.003(2) 0.000(3) 0.008(3) C25A 0.020(3) 0.024(3) 0.033(3) 0.000(2) 0.006(2) 0.002(2) C26A 0.037(4) 0.022(3) 0.037(3) -0.001(3) 0.011(3) -0.002(3) C27A 0.030(3) 0.014(3) 0.027(3) 0.007(2) -0.001(3) 0.006(2) C28A 0.028(3) 0.022(3) 0.023(3) 0.007(2) 0.005(2) -0.001(2) C29A 0.030(3) 0.024(3) 0.028(3) 0.003(2) 0.004(3) 0.000(3) C30A 0.043(4) 0.023(3) 0.026(3) -0.003(2) -0.001(3) -0.003(3) C31A 0.031(3) 0.023(3) 0.035(3) 0.015(3) -0.005(3) -0.008(3) C32A 0.027(3) 0.022(3) 0.037(3) 0.005(3) 0.002(3) 0.003(3) C33A 0.031(3) 0.025(3) 0.039(3) 0.003(3) -0.001(3) 0.001(3) O1W 0.114(5) 0.106(5) 0.123(5) 0.030(4) 0.016(4) 0.019(4) O2W 0.030(2) 0.031(2) 0.051(2) 0.0047(18) 0.0021(18) -0.0059(18) O3W 0.041(2) 0.050(3) 0.040(2) 0.0059(19) 0.0135(18) 0.009(2) O4W 0.034(2) 0.028(2) 0.047(2) 0.0063(18) -0.0071(18) -0.0007(18) O5W 0.031(2) 0.0202(19) 0.041(2) 0.0044(17) 0.0063(17) -0.0007(17) O6W 0.049(5) 0.030(5) 0.026(4) 0.003(3) -0.007(4) 0.009(4) O7W 0.032(5) 0.038(5) 0.035(4) -0.004(4) 0.005(4) 0.007(4) O61W 0.041(5) 0.029(5) 0.056(5) 0.006(4) -0.001(4) -0.002(4) _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 1.418(5) . ? O1 C12 1.428(5) . ? O2 C2 1.367(5) . ? O2 C22 1.425(5) . ? O3 C3 1.378(6) . ? O3 C23 1.424(5) . ? O4 C9 1.227(5) . ? N1 C9 1.361(6) . ? N1 C6 1.426(6) . ? N1 C8 1.477(5) . ? N2 C15 1.502(6) . ? N2 C16 1.509(6) . ? N2 C21 1.525(6) . ? N2 H24 0.9300 . ? C1 C6 1.389(6) . ? C1 C2 1.392(6) . ? C1 H1 0.9500 . ? C2 C3 1.392(6) . ? C3 C4 1.383(6) . ? C4 C5 1.407(6) . ? C4 H4 0.9500 . ? C5 C6 1.372(6) . ? C5 C7 1.500(6) . ? C7 C17 1.512(7) . ? C7 C21 1.532(6) . ? C7 C8 1.563(6) . ? C8 C18 1.513(6) . ? C8 H8 1.0000 . ? C9 C10 1.511(7) . ? C10 C11 1.538(6) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C18 1.532(6) . ? C11 H11 1.0000 . ? C12 C13 1.512(6) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.322(6) . ? C13 H13 0.9500 . ? C14 C19 1.503(6) . ? C14 C15 1.511(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 1.527(6) . ? C18 H18 1.0000 . ? C19 C20 1.560(6) . ? C19 H19 1.0000 . ? C20 C21 1.526(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 . ? O1A C11A 1.414(5) . ? O1A C12A 1.424(5) . ? O2A C2A 1.366(5) . ? O2A C22A 1.428(5) . ? O3A C3A 1.383(5) . ? O3A C23A 1.440(5) . ? O4A C9A 1.229(5) . ? N1A C9A 1.349(6) . ? N1A C6A 1.439(6) . ? N1A C8A 1.473(5) . ? N2A C16A 1.495(6) . ? N2A C15A 1.500(6) . ? N2A C21A 1.520(5) . ? N2A H24A 0.9300 . ? C1A C2A 1.393(6) . ? C1A C6A 1.394(6) . ? C1A H1A 0.9500 . ? C2A C3A 1.404(6) . ? C3A C4A 1.375(6) . ? C4A C5A 1.395(6) . ? C4A H4A 0.9500 . ? C5A C6A 1.373(6) . ? C5A C7A 1.498(6) . ? C7A C17A 1.539(6) . ? C7A C21A 1.550(6) . ? C7A C8A 1.552(6) . ? C8A C18A 1.533(6) . ? C8A H8A 1.0000 . ? C9A C10A 1.529(7) . ? C10A C11A 1.536(6) . ? C10A H10C 0.9900 . ? C10A H10D 0.9900 . ? C11A C18A 1.533(6) . ? C11A H11A 1.0000 . ? C12A C13A 1.498(7) . ? C12A H12C 0.9900 . ? C12A H12D 0.9900 . ? C13A C14A 1.327(6) . ? C13A H13A 0.9500 . ? C14A C15A 1.495(6) . ? C14A C19A 1.506(6) . ? C15A H15C 0.9900 . ? C15A H15D 0.9900 . ? C16A C17A 1.520(6) . ? C16A H16C 0.9900 . ? C16A H16D 0.9900 . ? C17A H17C 0.9900 . ? C17A H17D 0.9900 . ? C18A C19A 1.530(6) . ? C18A H18A 1.0000 . ? C19A C20A 1.550(6) . ? C19A H19A 1.0000 . ? C20A C21A 1.506(6) . ? C20A H20C 0.9900 . ? C20A H20D 0.9900 . ? C21A H21A 1.0000 . ? C22A H22D 0.9800 . ? C22A H22E 0.9800 . ? C22A H22F 0.9800 . ? C23A H23D 0.9800 . ? C23A H23E 0.9800 . ? C23A H23F 0.9800 . ? O5 C24 1.253(6) . ? O6 C24 1.261(6) . ? O8 C27 1.219(6) . ? O9 N4 1.237(5) . ? O10 N4 1.224(5) . ? N3 C27 1.345(6) . ? N3 C25 1.453(6) . ? N3 H3 0.8800 . ? N4 C31 1.472(6) . ? C24 C25 1.511(7) . ? C25 C261 1.545(8) . ? C25 C26 1.547(8) . ? C25 H25 1.0000 . ? C26 O7 1.432(9) . ? C26 H26A 0.9900 . ? C26 H26B 0.9900 . ? O7 H7 0.8198 . ? C261 O71 1.431(9) . ? C261 H261 0.9900 . ? C261 H262 0.9900 . ? O71 H7 0.5111 . ? O71 H71 0.8435 . ? C27 C28 1.510(7) . ? C28 C33 1.387(7) . ? C28 C29 1.405(6) . ? C29 C30 1.377(6) . ? C29 H29 0.9500 . ? C30 C31 1.368(6) . ? C30 H30 0.9500 . ? C31 C32 1.395(6) . ? C32 C33 1.396(6) . ? C32 H32 0.9500 . ? C33 H33 0.9500 . ? O5A C24A 1.274(6) . ? O6A C24A 1.241(6) . ? O7A C26A 1.449(6) . ? O7A H7A 0.8881 . ? O8A C27A 1.234(6) . ? O9A N4A 1.225(5) . ? O10A N4A 1.241(5) . ? N3A C27A 1.339(6) . ? N3A C25A 1.461(6) . ? N3A H3A 0.8800 . ? N4A C31A 1.470(7) . ? C24A C25A 1.514(6) . ? C25A C26A 1.513(6) . ? C25A H25A 1.0000 . ? C26A H26C 0.9900 . ? C26A H26D 0.9900 . ? C27A C28A 1.497(7) . ? C28A C33A 1.391(7) . ? C28A C29A 1.398(6) . ? C29A C30A 1.367(7) . ? C29A H29A 0.9500 . ? C30A C31A 1.371(7) . ? C30A H30A 0.9500 . ? C31A C32A 1.361(7) . ? C32A C33A 1.388(7) . ? C32A H32A 0.9500 . ? C33A H33A 0.9500 . ? O1W H11W 0.8866 . ? O1W H12W 0.8452 . ? O2W H21W 0.8572 . ? O2W H22W 0.8528 . ? O3W H31W 0.8549 . ? O3W H32W 0.8588 . ? O4W H41W 0.8616 . ? O4W H42W 0.8606 . ? O5W H51W 0.8621 . ? O5W H52W 0.8652 . ? O6W H61W 0.9127 . ? O6W H62W 0.8592 . ? O6W H63W 1.2672 . ? O7W H71W 0.8347 . ? O7W H72W 0.8861 . ? O7W H64W 1.2198 . ? O61W H71W 0.5778 . ? O61W H72W 1.4007 . ? O61W H63W 1.0665 . ? O61W H64W 0.8494 . ? 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(4) . . ? C2 O2 C22 116.6(4) . . ? C3 O3 C23 116.2(4) . . ? C9 N1 C6 125.0(4) . . ? C9 N1 C8 119.5(4) . . ? C6 N1 C8 109.4(3) . . ? C15 N2 C16 111.6(4) . . ? C15 N2 C21 113.3(4) . . ? C16 N2 C21 107.4(3) . . ? C15 N2 H24 108.2 . . ? C16 N2 H24 108.2 . . ? C21 N2 H24 108.2 . . ? C6 C1 C2 117.0(4) . . ? C6 C1 H1 121.5 . . ? C2 C1 H1 121.5 . . ? O2 C2 C1 122.5(4) . . ? O2 C2 C3 116.4(4) . . ? C1 C2 C3 121.0(4) . . ? O3 C3 C4 123.7(4) . . ? O3 C3 C2 114.8(4) . . ? C4 C3 C2 121.4(4) . . ? C3 C4 C5 117.6(5) . . ? C3 C4 H4 121.2 . . ? C5 C4 H4 121.2 . . ? C6 C5 C4 120.2(5) . . ? C6 C5 C7 111.3(4) . . ? C4 C5 C7 127.9(4) . . ? C5 C6 C1 122.6(4) . . ? C5 C6 N1 109.5(4) . . ? C1 C6 N1 127.9(4) . . ? C5 C7 C17 112.8(4) . . ? C5 C7 C21 116.5(4) . . ? C17 C7 C21 101.7(4) . . ? C5 C7 C8 101.8(4) . . ? C17 C7 C8 110.6(4) . . ? C21 C7 C8 113.8(4) . . ? N1 C8 C18 106.8(4) . . ? N1 C8 C7 104.5(3) . . ? C18 C8 C7 117.6(4) . . ? N1 C8 H8 109.2 . . ? C18 C8 H8 109.2 . . ? C7 C8 H8 109.2 . . ? O4 C9 N1 122.7(5) . . ? O4 C9 C10 121.5(4) . . ? N1 C9 C10 115.9(4) . . ? C9 C10 C11 118.3(4) . . ? 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 114.9(4) . . ? O1 C11 C10 105.7(4) . . ? C18 C11 C10 109.3(4) . . ? O1 C11 H11 108.9 . . ? C18 C11 H11 108.9 . . ? C10 C11 H11 108.9 . . ? O1 C12 C13 112.5(4) . . ? O1 C12 H12A 109.1 . . ? C13 C12 H12A 109.1 . . ? O1 C12 H12B 109.1 . . ? C13 C12 H12B 109.1 . . ? H12A C12 H12B 107.8 . . ? C14 C13 C12 121.6(5) . . ? C14 C13 H13 119.2 . . ? C12 C13 H13 119.2 . . ? C13 C14 C19 123.3(4) . . ? C13 C14 C15 120.7(4) . . ? C19 C14 C15 116.0(4) . . ? N2 C15 C14 109.6(3) . . ? N2 C15 H15A 109.8 . . ? C14 C15 H15A 109.8 . . ? N2 C15 H15B 109.8 . . ? C14 C15 H15B 109.8 . . ? H15A C15 H15B 108.2 . . ? N2 C16 C17 103.3(4) . . ? N2 C16 H16A 111.1 . . ? C17 C16 H16A 111.1 . . ? N2 C16 H16B 111.1 . . ? C17 C16 H16B 111.1 . . ? H16A C16 H16B 109.1 . . ? C7 C17 C16 103.9(4) . . ? C7 C17 H17A 111.0 . . ? C16 C17 H17A 111.0 . . ? C7 C17 H17B 111.0 . . ? C16 C17 H17B 111.0 . . ? H17A C17 H17B 109.0 . . ? C8 C18 C19 112.8(4) . . ? C8 C18 C11 107.7(4) . . ? C19 C18 C11 116.9(4) . . ? C8 C18 H18 106.2 . . ? C19 C18 H18 106.2 . . ? C11 C18 H18 106.2 . . ? C14 C19 C18 115.4(4) . . ? C14 C19 C20 108.8(4) . . ? C18 C19 C20 105.9(4) . . ? C14 C19 H19 108.9 . . ? C18 C19 H19 108.9 . . ? C20 C19 H19 108.9 . . ? C21 C20 C19 107.6(4) . . ? C21 C20 H20A 110.2 . . ? C19 C20 H20A 110.2 . . ? C21 C20 H20B 110.2 . . ? C19 C20 H20B 110.2 . . ? H20A C20 H20B 108.5 . . ? C20 C21 N2 110.7(4) . . ? C20 C21 C7 115.6(4) . . ? N2 C21 C7 105.3(4) . . ? C20 C21 H21 108.3 . . ? N2 C21 H21 108.3 . . ? C7 C21 H21 108.3 . . ? 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 . . ? C11A O1A C12A 114.9(4) . . ? C2A O2A C22A 116.8(3) . . ? C3A O3A C23A 116.0(3) . . ? C9A N1A C6A 124.8(4) . . ? C9A N1A C8A 121.7(4) . . ? C6A N1A C8A 109.0(4) . . ? C16A N2A C15A 113.0(4) . . ? C16A N2A C21A 108.7(3) . . ? C15A N2A C21A 113.3(4) . . ? C16A N2A H24A 107.1 . . ? C15A N2A H24A 107.1 . . ? C21A N2A H24A 107.1 . . ? C2A C1A C6A 116.9(4) . . ? C2A C1A H1A 121.6 . . ? C6A C1A H1A 121.6 . . ? O2A C2A C1A 123.4(4) . . ? O2A C2A C3A 115.8(4) . . ? C1A C2A C3A 120.8(4) . . ? C4A C3A O3A 123.8(4) . . ? C4A C3A C2A 120.7(4) . . ? O3A C3A C2A 115.5(4) . . ? C3A C4A C5A 119.2(4) . . ? C3A C4A H4A 120.4 . . ? C5A C4A H4A 120.4 . . ? C6A C5A C4A 119.5(4) . . ? C6A C5A C7A 111.2(4) . . ? C4A C5A C7A 129.1(4) . . ? C5A C6A C1A 122.9(4) . . ? C5A C6A N1A 109.6(4) . . ? C1A C6A N1A 127.5(4) . . ? C5A C7A C17A 111.2(4) . . ? C5A C7A C21A 116.3(4) . . ? C17A C7A C21A 101.6(3) . . ? C5A C7A C8A 102.8(3) . . ? C17A C7A C8A 111.0(4) . . ? C21A C7A C8A 114.2(4) . . ? N1A C8A C18A 105.8(3) . . ? N1A C8A C7A 105.1(3) . . ? C18A C8A C7A 116.9(4) . . ? N1A C8A H8A 109.6 . . ? C18A C8A H8A 109.6 . . ? C7A C8A H8A 109.6 . . ? O4A C9A N1A 123.3(5) . . ? O4A C9A C10A 120.9(4) . . ? N1A C9A C10A 115.8(4) . . ? C9A C10A C11A 118.2(4) . . ? C9A C10A H10C 107.8 . . ? C11A C10A H10C 107.8 . . ? C9A C10A H10D 107.8 . . ? C11A C10A H10D 107.8 . . ? H10C C10A H10D 107.1 . . ? O1A C11A C18A 112.7(4) . . ? O1A C11A C10A 105.8(4) . . ? C18A C11A C10A 110.8(4) . . ? O1A C11A H11A 109.2 . . ? C18A C11A H11A 109.2 . . ? C10A C11A H11A 109.2 . . ? O1A C12A C13A 112.9(4) . . ? O1A C12A H12C 109.0 . . ? C13A C12A H12C 109.0 . . ? O1A C12A H12D 109.0 . . ? C13A C12A H12D 109.0 . . ? H12C C12A H12D 107.8 . . ? C14A C13A C12A 124.1(5) . . ? C14A C13A H13A 117.9 . . ? C12A C13A H13A 117.9 . . ? C13A C14A C15A 121.9(4) . . ? C13A C14A C19A 122.8(4) . . ? C15A C14A C19A 115.2(4) . . ? C14A C15A N2A 108.2(4) . . ? C14A C15A H15C 110.1 . . ? N2A C15A H15C 110.1 . . ? C14A C15A H15D 110.1 . . ? N2A C15A H15D 110.1 . . ? H15C C15A H15D 108.4 . . ? N2A C16A C17A 104.1(4) . . ? N2A C16A H16C 110.9 . . ? C17A C16A H16C 110.9 . . ? N2A C16A H16D 110.9 . . ? C17A C16A H16D 110.9 . . ? H16C C16A H16D 108.9 . . ? C16A C17A C7A 103.4(4) . . ? C16A C17A H17C 111.1 . . ? C7A C17A H17C 111.1 . . ? C16A C17A H17D 111.1 . . ? C7A C17A H17D 111.1 . . ? H17C C17A H17D 109.0 . . ? C19A C18A C11A 119.1(4) . . ? C19A C18A C8A 112.3(4) . . ? C11A C18A C8A 106.3(4) . . ? C19A C18A H18A 106.1 . . ? C11A C18A H18A 106.1 . . ? C8A C18A H18A 106.1 . . ? C14A C19A C18A 115.5(4) . . ? C14A C19A C20A 109.7(4) . . ? C18A C19A C20A 106.0(4) . . ? C14A C19A H19A 108.5 . . ? C18A C19A H19A 108.5 . . ? C20A C19A H19A 108.5 . . ? C21A C20A C19A 107.1(4) . . ? C21A C20A H20C 110.3 . . ? C19A C20A H20C 110.3 . . ? C21A C20A H20D 110.3 . . ? C19A C20A H20D 110.3 . . ? H20C C20A H20D 108.6 . . ? C20A C21A N2A 111.4(4) . . ? C20A C21A C7A 115.5(4) . . ? N2A C21A C7A 104.5(4) . . ? C20A C21A H21A 108.4 . . ? N2A C21A H21A 108.4 . . ? C7A C21A H21A 108.4 . . ? O2A C22A H22D 109.5 . . ? O2A C22A H22E 109.5 . . ? H22D C22A H22E 109.5 . . ? O2A C22A H22F 109.5 . . ? H22D C22A H22F 109.5 . . ? H22E C22A H22F 109.5 . . ? O3A C23A H23D 109.5 . . ? O3A C23A H23E 109.5 . . ? H23D C23A H23E 109.5 . . ? O3A C23A H23F 109.5 . . ? H23D C23A H23F 109.5 . . ? H23E C23A H23F 109.5 . . ? C27 N3 C25 121.3(4) . . ? C27 N3 H3 119.3 . . ? C25 N3 H3 119.3 . . ? O10 N4 O9 123.1(4) . . ? O10 N4 C31 118.7(4) . . ? O9 N4 C31 118.2(4) . . ? O5 C24 O6 126.3(5) . . ? O5 C24 C25 118.7(5) . . ? O6 C24 C25 115.0(5) . . ? N3 C25 C24 111.2(4) . . ? N3 C25 C261 108.8(7) . . ? C24 C25 C261 105.3(7) . . ? N3 C25 C26 110.0(7) . . ? C24 C25 C26 119.8(7) . . ? C261 C25 C26 18.5(6) . . ? N3 C25 H25 104.8 . . ? C24 C25 H25 104.8 . . ? C261 C25 H25 121.8 . . ? C26 C25 H25 104.8 . . ? O7 C26 C25 112.2(7) . . ? O7 C26 H26A 109.2 . . ? C25 C26 H26A 109.2 . . ? O7 C26 H26B 109.2 . . ? C25 C26 H26B 109.2 . . ? H26A C26 H26B 107.9 . . ? C26 O7 H7 135.1 . . ? O71 C261 C25 112.1(7) . . ? O71 C261 H261 109.2 . . ? C25 C261 H261 109.2 . . ? O71 C261 H262 109.2 . . ? C25 C261 H262 109.2 . . ? H261 C261 H262 107.9 . . ? C261 O71 H7 111.4 . . ? C261 O71 H71 111.8 . . ? H7 O71 H71 125.5 . . ? O8 C27 N3 122.5(5) . . ? O8 C27 C28 120.6(5) . . ? N3 C27 C28 116.9(5) . . ? C33 C28 C29 120.4(5) . . ? C33 C28 C27 124.0(4) . . ? C29 C28 C27 115.6(5) . . ? C30 C29 C28 119.9(5) . . ? C30 C29 H29 120.0 . . ? C28 C29 H29 120.0 . . ? C31 C30 C29 118.7(4) . . ? C31 C30 H30 120.7 . . ? C29 C30 H30 120.7 . . ? C30 C31 C32 123.4(4) . . ? C30 C31 N4 118.6(4) . . ? C32 C31 N4 117.9(4) . . ? C31 C32 C33 117.4(5) . . ? C31 C32 H32 121.3 . . ? C33 C32 H32 121.3 . . ? C28 C33 C32 120.1(4) . . ? C28 C33 H33 119.9 . . ? C32 C33 H33 119.9 . . ? C26A O7A H7A 113.7 . . ? C27A N3A C25A 121.0(4) . . ? C27A N3A H3A 119.5 . . ? C25A N3A H3A 119.5 . . ? O9A N4A O10A 124.3(5) . . ? O9A N4A C31A 117.6(5) . . ? O10A N4A C31A 118.1(5) . . ? O6A C24A O5A 126.5(5) . . ? O6A C24A C25A 119.9(5) . . ? O5A C24A C25A 113.6(5) . . ? N3A C25A C26A 112.7(4) . . ? N3A C25A C24A 109.9(4) . . ? C26A C25A C24A 110.4(4) . . ? N3A C25A H25A 107.9 . . ? C26A C25A H25A 107.9 . . ? C24A C25A H25A 107.9 . . ? O7A C26A C25A 109.3(4) . . ? O7A C26A H26C 109.8 . . ? C25A C26A H26C 109.8 . . ? O7A C26A H26D 109.8 . . ? C25A C26A H26D 109.8 . . ? H26C C26A H26D 108.3 . . ? O8A C27A N3A 121.9(5) . . ? O8A C27A C28A 120.5(4) . . ? N3A C27A C28A 117.6(5) . . ? C33A C28A C29A 119.3(5) . . ? C33A C28A C27A 123.5(5) . . ? C29A C28A C27A 117.2(5) . . ? C30A C29A C28A 120.5(5) . . ? C30A C29A H29A 119.8 . . ? C28A C29A H29A 119.8 . . ? C29A C30A C31A 118.6(5) . . ? C29A C30A H30A 120.7 . . ? C31A C30A H30A 120.7 . . ? C32A C31A C30A 123.2(5) . . ? C32A C31A N4A 118.5(5) . . ? C30A C31A N4A 118.3(5) . . ? C31A C32A C33A 118.4(5) . . ? C31A C32A H32A 120.8 . . ? C33A C32A H32A 120.8 . . ? C32A C33A C28A 120.1(5) . . ? C32A C33A H33A 120.0 . . ? C28A C33A H33A 120.0 . . ? H11W O1W H12W 118.9 . . ? H21W O2W H22W 108.3 . . ? H31W O3W H32W 107.9 . . ? H41W O4W H42W 111.9 . . ? H51W O5W H52W 107.5 . . ? H61W O6W H62W 113.9 . . ? H61W O6W H63W 98.1 . . ? H62W O6W H63W 62.9 . . ? H71W O7W H72W 109.5 . . ? H71W O7W H64W 67.5 . . ? H72W O7W H64W 42.4 . . ? H71W O61W H72W 78.6 . . ? H71W O61W H63W 108.1 . . ? H72W O61W H63W 145.7 . . ? H71W O61W H64W 110.8 . . ? H72W O61W H64W 32.5 . . ? H63W O61W H64W 130.9 . . ? 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 -1.8(6) . . . . ? C22 O2 C2 C3 -179.9(4) . . . . ? C6 C1 C2 O2 -177.8(4) . . . . ? C6 C1 C2 C3 0.3(7) . . . . ? C23 O3 C3 C4 1.5(7) . . . . ? C23 O3 C3 C2 -177.9(4) . . . . ? O2 C2 C3 O3 -4.4(6) . . . . ? C1 C2 C3 O3 177.5(4) . . . . ? O2 C2 C3 C4 176.3(4) . . . . ? C1 C2 C3 C4 -1.9(8) . . . . ? O3 C3 C4 C5 -177.9(5) . . . . ? C2 C3 C4 C5 1.4(7) . . . . ? C3 C4 C5 C6 0.7(7) . . . . ? C3 C4 C5 C7 -170.7(5) . . . . ? C4 C5 C6 C1 -2.3(8) . . . . ? C7 C5 C6 C1 170.4(4) . . . . ? C4 C5 C6 N1 177.9(4) . . . . ? C7 C5 C6 N1 -9.4(6) . . . . ? C2 C1 C6 C5 1.8(7) . . . . ? C2 C1 C6 N1 -178.4(5) . . . . ? C9 N1 C6 C5 -155.4(4) . . . . ? C8 N1 C6 C5 -3.3(5) . . . . ? C9 N1 C6 C1 24.8(8) . . . . ? C8 N1 C6 C1 176.9(4) . . . . ? C6 C5 C7 C17 -101.4(5) . . . . ? C4 C5 C7 C17 70.6(7) . . . . ? C6 C5 C7 C21 141.5(4) . . . . ? C4 C5 C7 C21 -46.4(7) . . . . ? C6 C5 C7 C8 17.1(5) . . . . ? C4 C5 C7 C8 -170.8(5) . . . . ? C9 N1 C8 C18 42.3(5) . . . . ? C6 N1 C8 C18 -111.6(4) . . . . ? C9 N1 C8 C7 167.6(4) . . . . ? C6 N1 C8 C7 13.7(5) . . . . ? C5 C7 C8 N1 -17.9(5) . . . . ? C17 C7 C8 N1 102.2(4) . . . . ? C21 C7 C8 N1 -144.0(4) . . . . ? C5 C7 C8 C18 100.4(5) . . . . ? C17 C7 C8 C18 -139.6(4) . . . . ? C21 C7 C8 C18 -25.8(6) . . . . ? C6 N1 C9 O4 -21.5(7) . . . . ? C8 N1 C9 O4 -171.0(4) . . . . ? C6 N1 C9 C10 158.8(5) . . . . ? C8 N1 C9 C10 9.2(6) . . . . ? O4 C9 C10 C11 146.5(5) . . . . ? N1 C9 C10 C11 -33.7(7) . . . . ? C12 O1 C11 C18 -68.8(5) . . . . ? C12 O1 C11 C10 170.5(4) . . . . ? C9 C10 C11 O1 127.4(5) . . . . ? C9 C10 C11 C18 3.2(6) . . . . ? C11 O1 C12 C13 87.4(5) . . . . ? O1 C12 C13 C14 -61.4(6) . . . . ? C12 C13 C14 C19 -5.4(7) . . . . ? C12 C13 C14 C15 175.6(4) . . . . ? C16 N2 C15 C14 74.2(5) . . . . ? C21 N2 C15 C14 -47.1(5) . . . . ? C13 C14 C15 N2 -126.6(5) . . . . ? C19 C14 C15 N2 54.4(5) . . . . ? C15 N2 C16 C17 -143.0(4) . . . . ? C21 N2 C16 C17 -18.3(5) . . . . ? C5 C7 C17 C16 -168.4(4) . . . . ? C21 C7 C17 C16 -42.9(5) . . . . ? C8 C7 C17 C16 78.4(5) . . . . ? N2 C16 C17 C7 38.3(5) . . . . ? N1 C8 C18 C19 158.1(4) . . . . ? C7 C8 C18 C19 41.0(6) . . . . ? N1 C8 C18 C11 -71.4(5) . . . . ? C7 C8 C18 C11 171.6(4) . . . . ? O1 C11 C18 C8 -71.4(5) . . . . ? C10 C11 C18 C8 47.2(5) . . . . ? O1 C11 C18 C19 56.8(6) . . . . ? C10 C11 C18 C19 175.4(4) . . . . ? C13 C14 C19 C18 60.3(6) . . . . ? C15 C14 C19 C18 -120.7(4) . . . . ? C13 C14 C19 C20 179.1(4) . . . . ? C15 C14 C19 C20 -1.9(5) . . . . ? C8 C18 C19 C14 58.7(5) . . . . ? C11 C18 C19 C14 -67.0(6) . . . . ? C8 C18 C19 C20 -61.6(5) . . . . ? C11 C18 C19 C20 172.7(4) . . . . ? C14 C19 C20 C21 -55.7(5) . . . . ? C18 C19 C20 C21 68.8(5) . . . . ? C19 C20 C21 N2 62.7(5) . . . . ? C19 C20 C21 C7 -56.9(5) . . . . ? C15 N2 C21 C20 -9.8(5) . . . . ? C16 N2 C21 C20 -133.5(4) . . . . ? C15 N2 C21 C7 115.8(4) . . . . ? C16 N2 C21 C7 -7.9(5) . . . . ? C5 C7 C21 C20 -83.5(5) . . . . ? C17 C7 C21 C20 153.5(4) . . . . ? C8 C7 C21 C20 34.5(6) . . . . ? C5 C7 C21 N2 154.0(4) . . . . ? C17 C7 C21 N2 31.0(4) . . . . ? C8 C7 C21 N2 -88.1(5) . . . . ? C22A O2A C2A C1A -6.0(6) . . . . ? C22A O2A C2A C3A 172.4(4) . . . . ? C6A C1A C2A O2A 179.4(4) . . . . ? C6A C1A C2A C3A 1.0(7) . . . . ? C23A O3A C3A C4A 0.2(6) . . . . ? C23A O3A C3A C2A -179.0(4) . . . . ? O2A C2A C3A C4A 179.5(4) . . . . ? C1A C2A C3A C4A -2.1(7) . . . . ? O2A C2A C3A O3A -1.3(6) . . . . ? C1A C2A C3A O3A 177.2(4) . . . . ? O3A C3A C4A C5A -177.8(4) . . . . ? C2A C3A C4A C5A 1.3(7) . . . . ? C3A C4A C5A C6A 0.4(7) . . . . ? C3A C4A C5A C7A -174.8(4) . . . . ? C4A C5A C6A C1A -1.4(7) . . . . ? C7A C5A C6A C1A 174.5(4) . . . . ? C4A C5A C6A N1A 178.4(4) . . . . ? C7A C5A C6A N1A -5.6(5) . . . . ? C2A C1A C6A C5A 0.7(7) . . . . ? C2A C1A C6A N1A -179.1(4) . . . . ? C9A N1A C6A C5A -161.0(4) . . . . ? C8A N1A C6A C5A -4.7(5) . . . . ? C9A N1A C6A C1A 18.9(7) . . . . ? C8A N1A C6A C1A 175.2(4) . . . . ? C6A C5A C7A C17A -106.1(4) . . . . ? C4A C5A C7A C17A 69.4(6) . . . . ? C6A C5A C7A C21A 138.3(4) . . . . ? C4A C5A C7A C21A -46.2(7) . . . . ? C6A C5A C7A C8A 12.8(5) . . . . ? C4A C5A C7A C8A -171.8(5) . . . . ? C9A N1A C8A C18A 45.2(5) . . . . ? C6A N1A C8A C18A -112.0(4) . . . . ? C9A N1A C8A C7A 169.5(4) . . . . ? C6A N1A C8A C7A 12.3(5) . . . . ? C5A C7A C8A N1A -14.7(4) . . . . ? C17A C7A C8A N1A 104.3(4) . . . . ? C21A C7A C8A N1A -141.6(4) . . . . ? C5A C7A C8A C18A 102.3(4) . . . . ? C17A C7A C8A C18A -138.7(4) . . . . ? C21A C7A C8A C18A -24.6(5) . . . . ? C6A N1A C9A O4A -25.8(7) . . . . ? C8A N1A C9A O4A -179.2(4) . . . . ? C6A N1A C9A C10A 156.8(4) . . . . ? C8A N1A C9A C10A 3.3(6) . . . . ? O4A C9A C10A C11A 156.3(4) . . . . ? N1A C9A C10A C11A -26.2(7) . . . . ? C12A O1A C11A C18A -71.0(5) . . . . ? C12A O1A C11A C10A 167.8(3) . . . . ? C9A C10A C11A O1A 119.6(5) . . . . ? C9A C10A C11A C18A -2.8(6) . . . . ? C11A O1A C12A C13A 86.9(5) . . . . ? O1A C12A C13A C14A -60.3(7) . . . . ? C12A C13A C14A C15A 174.4(5) . . . . ? C12A C13A C14A C19A -2.9(8) . . . . ? C13A C14A C15A N2A -121.4(5) . . . . ? C19A C14A C15A N2A 56.1(5) . . . . ? C16A N2A C15A C14A 74.8(5) . . . . ? C21A N2A C15A C14A -49.5(5) . . . . ? C15A N2A C16A C17A -143.6(4) . . . . ? C21A N2A C16A C17A -16.9(5) . . . . ? N2A C16A C17A C7A 36.7(4) . . . . ? C5A C7A C17A C16A -166.4(4) . . . . ? C21A C7A C17A C16A -42.0(4) . . . . ? C8A C7A C17A C16A 79.8(4) . . . . ? O1A C11A C18A C19A 59.5(5) . . . . ? C10A C11A C18A C19A 177.8(4) . . . . ? O1A C11A C18A C8A -68.5(4) . . . . ? C10A C11A C18A C8A 49.8(5) . . . . ? N1A C8A C18A C19A 156.8(4) . . . . ? C7A C8A C18A C19A 40.1(5) . . . . ? N1A C8A C18A C11A -71.3(4) . . . . ? C7A C8A C18A C11A 172.1(4) . . . . ? C13A C14A C19A C18A 54.4(6) . . . . ? C15A C14A C19A C18A -123.1(5) . . . . ? C13A C14A C19A C20A 174.1(4) . . . . ? C15A C14A C19A C20A -3.4(6) . . . . ? C11A C18A C19A C14A -65.7(6) . . . . ? C8A C18A C19A C14A 59.4(5) . . . . ? C11A C18A C19A C20A 172.5(4) . . . . ? C8A C18A C19A C20A -62.3(5) . . . . ? C14A C19A C20A C21A -54.8(5) . . . . ? C18A C19A C20A C21A 70.6(5) . . . . ? C19A C20A C21A N2A 61.2(5) . . . . ? C19A C20A C21A C7A -57.8(5) . . . . ? C16A N2A C21A C20A -134.7(4) . . . . ? C15A N2A C21A C20A -8.1(5) . . . . ? C16A N2A C21A C7A -9.4(5) . . . . ? C15A N2A C21A C7A 117.2(4) . . . . ? C5A C7A C21A C20A -85.1(5) . . . . ? C17A C7A C21A C20A 154.0(4) . . . . ? C8A C7A C21A C20A 34.4(5) . . . . ? C5A C7A C21A N2A 152.2(4) . . . . ? C17A C7A C21A N2A 31.3(4) . . . . ? C8A C7A C21A N2A -88.3(4) . . . . ? C27 N3 C25 C24 151.5(4) . . . . ? C27 N3 C25 C261 -93.0(7) . . . . ? C27 N3 C25 C26 -73.4(7) . . . . ? O5 C24 C25 N3 10.3(6) . . . . ? O6 C24 C25 N3 -170.2(4) . . . . ? O5 C24 C25 C261 -107.4(7) . . . . ? O6 C24 C25 C261 72.1(7) . . . . ? O5 C24 C25 C26 -119.8(7) . . . . ? O6 C24 C25 C26 59.7(8) . . . . ? N3 C25 C26 O7 -54.9(12) . . . . ? C24 C25 C26 O7 75.7(12) . . . . ? C261 C25 C26 O7 35(3) . . . . ? N3 C25 C261 O71 -61.4(13) . . . . ? C24 C25 C261 O71 57.8(13) . . . . ? C26 C25 C261 O71 -158(5) . . . . ? C25 N3 C27 O8 -4.3(7) . . . . ? C25 N3 C27 C28 174.7(4) . . . . ? O8 C27 C28 C33 -163.6(5) . . . . ? N3 C27 C28 C33 17.4(7) . . . . ? O8 C27 C28 C29 18.5(7) . . . . ? N3 C27 C28 C29 -160.4(4) . . . . ? C33 C28 C29 C30 -2.0(7) . . . . ? C27 C28 C29 C30 175.9(4) . . . . ? C28 C29 C30 C31 -1.4(7) . . . . ? C29 C30 C31 C32 4.0(7) . . . . ? C29 C30 C31 N4 -174.0(4) . . . . ? O10 N4 C31 C30 167.0(4) . . . . ? O9 N4 C31 C30 -11.4(6) . . . . ? O10 N4 C31 C32 -11.1(6) . . . . ? O9 N4 C31 C32 170.5(4) . . . . ? C30 C31 C32 C33 -3.0(7) . . . . ? N4 C31 C32 C33 175.0(4) . . . . ? C29 C28 C33 C32 3.0(7) . . . . ? C27 C28 C33 C32 -174.7(4) . . . . ? C31 C32 C33 C28 -0.6(7) . . . . ? C27A N3A C25A C26A -67.6(5) . . . . ? C27A N3A C25A C24A 168.7(4) . . . . ? O6A C24A C25A N3A 5.8(6) . . . . ? O5A C24A C25A N3A -176.7(4) . . . . ? O6A C24A C25A C26A -119.1(5) . . . . ? O5A C24A C25A C26A 58.4(5) . . . . ? N3A C25A C26A O7A -74.8(5) . . . . ? C24A C25A C26A O7A 48.5(6) . . . . ? C25A N3A C27A O8A 1.4(7) . . . . ? C25A N3A C27A C28A -177.4(4) . . . . ? O8A C27A C28A C33A 163.2(5) . . . . ? N3A C27A C28A C33A -18.0(7) . . . . ? O8A C27A C28A C29A -16.9(6) . . . . ? N3A C27A C28A C29A 161.8(4) . . . . ? C33A C28A C29A C30A 0.0(7) . . . . ? C27A C28A C29A C30A -179.9(4) . . . . ? C28A C29A C30A C31A 1.2(7) . . . . ? C29A C30A C31A C32A -1.9(7) . . . . ? C29A C30A C31A N4A 175.5(4) . . . . ? O9A N4A C31A C32A -156.6(5) . . . . ? O10A N4A C31A C32A 24.2(7) . . . . ? O9A N4A C31A C30A 25.8(7) . . . . ? O10A N4A C31A C30A -153.4(5) . . . . ? C30A C31A C32A C33A 1.4(7) . . . . ? N4A C31A C32A C33A -176.1(4) . . . . ? C31A C32A C33A C28A -0.1(7) . . . . ? C29A C28A C33A C32A -0.6(7) . . . . ? C27A C28A C33A C32A 179.3(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 N2A H24A O5A 0.93 1.67 2.582(5) 168.1 . N2 H24 O5 0.93 1.79 2.701(5) 166.6 . O7A H7A O3W 0.89 1.91 2.763(5) 160.5 . O7 H7 O7W 0.82 1.97 2.710(10) 149.9 . O71 H71 O3W 0.84 2.20 2.924(9) 143.9 . O1W H11W O4 0.89 1.91 2.797(6) 179.4 2_546 O1W H12W O6 0.85 2.22 3.066(6) 178.1 . O2W H21W O6 0.86 1.88 2.707(5) 160.6 1_655 O2W H22W O10A 0.85 2.05 2.894(5) 172.7 1_445 O3W H31W O7W 0.85 2.12 2.909(8) 152.9 . O3W H31W O71 0.85 2.36 2.924(9) 123.8 . O3W H32W O2W 0.86 1.94 2.749(5) 157.5 . O4W H41W O5A 0.86 1.94 2.758(5) 158.2 . O4W H42W O5W 0.86 2.07 2.910(5) 164.3 1_455 O5W H51W O6A 0.86 2.02 2.753(5) 142.7 . O5W H52W O4A 0.87 2.02 2.874(4) 171.8 2_655 O6W H61W O6 0.91 2.01 2.919(7) 179.1 . O6W H62W O7A 0.86 1.78 2.585(8) 154.5 1_455 O7W H71W O6W 0.83 1.95 2.788(10) 179.2 . O7W H72W O4W 0.89 1.82 2.708(8) 178.8 . O61W H63W O7A 1.07 1.97 2.935(8) 148.2 1_455 O61W H64W O4W 0.85 1.97 2.820(8) 178.2 . _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.341 _refine_diff_density_min -0.375 _refine_diff_density_rms 0.054 # start Validation Reply Form _vrf_PLAT772_7 ; PROBLEM: Suspect O-H Bond in CIF: O61W -- H72W .. 1.40 Ang. RESPONSE: disordered water molecules ; # end Validation Reply Form #===== end data_8 _database_code_depnum_ccdc_archive 'CCDC 758149' #TrackingRef 'bialonska2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C23 H27 N2 O4, C10 H9 N2 O6, 4.5(H2 O1)' _chemical_formula_sum 'C33 H46 N4 O14.50' _chemical_formula_weight 730.74 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 7.371(3) _cell_length_b 12.151(4) _cell_length_c 19.098(5) _cell_angle_alpha 90.00 _cell_angle_beta 91.31(3) _cell_angle_gamma 90.00 _cell_volume 1710.1(10) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6030 _cell_measurement_theta_min 2.72 _cell_measurement_theta_max 28.42 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.419 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 776 _exptl_absorpt_coefficient_mu 0.112 _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 23948 _diffrn_reflns_av_R_equivalents 0.1005 _diffrn_reflns_av_sigmaI/netI 0.1256 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.71 _diffrn_reflns_theta_max 28.00 _reflns_number_total 4252 _reflns_number_gt 2288 _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, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1603P)^2^+0.8155P] 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 4252 _refine_ls_number_parameters 656 _refine_ls_number_restraints 293 _refine_ls_R_factor_all 0.1519 _refine_ls_R_factor_gt 0.0904 _refine_ls_wR_factor_ref 0.2762 _refine_ls_wR_factor_gt 0.2477 _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_restrained_S_all 1.013 _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 0.1922(6) 0.2716(5) 0.1351(3) 0.0312(13) Uani 1 1 d . . . O2 O 0.2381(7) 0.8442(5) -0.1316(3) 0.0363(14) Uani 1 1 d . . . O3 O 0.2814(7) 0.9672(5) -0.0208(3) 0.0347(14) Uani 1 1 d . . . O4 O 0.2240(8) 0.4453(6) -0.0835(4) 0.0455(16) Uani 1 1 d . . . N1 N 0.1533(9) 0.5219(6) 0.0213(4) 0.0311(16) Uani 1 1 d . . . N2 N 0.0966(8) 0.6254(6) 0.2513(4) 0.0311(16) Uani 1 1 d . . . H2 H 0.0784 0.6850 0.2809 0.037 Uiso 1 1 calc R . . C1 C 0.1923(10) 0.6790(7) -0.0645(5) 0.033(2) Uani 1 1 d . . . H1 H 0.1860 0.6332 -0.1048 0.040 Uiso 1 1 calc R . . C2 C 0.2224(9) 0.7943(8) -0.0698(4) 0.0282(18) Uani 1 1 d . . . C3 C 0.2351(10) 0.8539(7) -0.0093(5) 0.0309(19) Uani 1 1 d . . . C4 C 0.2092(10) 0.8125(7) 0.0562(5) 0.0312(19) Uani 1 1 d . . . H4 H 0.2134 0.8586 0.0964 0.037 Uiso 1 1 calc R . . C5 C 0.1756(10) 0.6975(7) 0.0618(4) 0.0275(18) Uani 1 1 d . . . C6 C 0.1725(10) 0.6357(7) 0.0033(5) 0.0316(19) Uani 1 1 d . . . C7 C 0.1244(10) 0.6329(7) 0.1231(4) 0.0281(17) Uani 1 1 d . . . C8 C 0.1518(10) 0.5127(6) 0.0981(4) 0.0291(18) Uani 1 1 d . . . H8 H 0.0469 0.4663 0.1124 0.035 Uiso 1 1 calc R . . C9 C 0.2096(10) 0.4358(7) -0.0210(5) 0.0324(19) Uani 1 1 d . . . C10 C 0.2543(11) 0.3302(8) 0.0184(5) 0.035(2) Uani 1 1 d . . . H10A H 0.3495 0.2914 -0.0078 0.042 Uiso 1 1 calc R . . H10B H 0.1447 0.2831 0.0163 0.042 Uiso 1 1 calc R . . C11 C 0.3182(10) 0.3363(7) 0.0951(4) 0.0297(18) Uani 1 1 d . . . H11 H 0.4415 0.3023 0.0996 0.036 Uiso 1 1 calc R . . C12 C 0.2452(11) 0.2494(7) 0.2034(5) 0.036(2) Uani 1 1 d . . . H12A H 0.3791 0.2431 0.2062 0.043 Uiso 1 1 calc R . . H12B H 0.1935 0.1778 0.2175 0.043 Uiso 1 1 calc R . . C13 C 0.1837(10) 0.3390(7) 0.2547(5) 0.0328(19) Uani 1 1 d . . . H13 H 0.1025 0.3207 0.2908 0.039 Uiso 1 1 calc R . . C14 C 0.2434(10) 0.4422(7) 0.2489(4) 0.0299(18) Uani 1 1 d . . . C15 C 0.1673(11) 0.5313(8) 0.2950(5) 0.037(2) Uani 1 1 d . . . H15A H 0.0678 0.5006 0.3230 0.044 Uiso 1 1 calc R . . H15B H 0.2634 0.5581 0.3278 0.044 Uiso 1 1 calc R . . C16 C -0.0842(10) 0.5978(8) 0.2155(5) 0.036(2) Uani 1 1 d . . . H16A H -0.0993 0.5172 0.2109 0.043 Uiso 1 1 calc R . . H16B H -0.1862 0.6275 0.2425 0.043 Uiso 1 1 calc R . . C17 C -0.0769(9) 0.6516(7) 0.1444(4) 0.0299(19) Uani 1 1 d . . . H17A H -0.1056 0.7311 0.1472 0.036 Uiso 1 1 calc R . . H17B H -0.1624 0.6161 0.1107 0.036 Uiso 1 1 calc R . . C18 C 0.3295(10) 0.4572(7) 0.1201(4) 0.0271(17) Uani 1 1 d . . . H18 H 0.4255 0.4926 0.0915 0.033 Uiso 1 1 calc R . . C19 C 0.3817(10) 0.4812(8) 0.1970(4) 0.032(2) Uani 1 1 d . . . H19 H 0.5003 0.4445 0.2082 0.039 Uiso 1 1 calc R . . C20 C 0.4076(10) 0.6044(6) 0.2028(5) 0.0279(18) Uani 1 1 d . . . H20A H 0.4921 0.6296 0.1665 0.033 Uiso 1 1 calc R . . H20B H 0.4613 0.6228 0.2493 0.033 Uiso 1 1 calc R . . C21 C 0.2255(11) 0.6628(8) 0.1930(5) 0.037(2) Uani 1 1 d . . . H21 H 0.2438 0.7443 0.1958 0.044 Uiso 1 1 calc R . . C22 C 0.2321(11) 0.7789(9) -0.1939(5) 0.042(2) Uani 1 1 d . . . H22A H 0.2465 0.8266 -0.2348 0.063 Uiso 1 1 calc R . . H22B H 0.1152 0.7407 -0.1976 0.063 Uiso 1 1 calc R . . H22C H 0.3305 0.7247 -0.1920 0.063 Uiso 1 1 calc R . . C23 C 0.3051(12) 1.0352(8) 0.0389(5) 0.040(2) Uani 1 1 d . . . H23A H 0.3481 1.1078 0.0244 0.060 Uiso 1 1 calc R . . H23B H 0.3945 1.0018 0.0711 0.060 Uiso 1 1 calc R . . H23C H 0.1890 1.0430 0.0624 0.060 Uiso 1 1 calc R . . O5 O 0.0529(15) 0.7979(10) 0.3270(7) 0.027(3) Uani 0.604(10) 1 d PU A 1 O6 O 0.3514(12) 0.7668(8) 0.3427(6) 0.016(2) Uani 0.604(10) 1 d PU A 1 O7 O 0.3076(11) 1.1226(7) 0.3574(4) 0.023(2) Uani 0.604(10) 1 d PDU A 1 H7 H 0.2121 1.1564 0.3673 0.034 Uiso 0.604(10) 1 calc PR A 1 O8 O 0.0796(13) 0.8188(10) 0.4977(5) 0.027(3) Uani 0.604(10) 1 d PU A 1 O9 O -0.740(2) 0.9368(14) 0.6485(8) 0.053(5) Uani 0.604(10) 1 d PU A 1 O10 O -0.7590(18) 1.0893(12) 0.5815(8) 0.049(4) Uani 0.604(10) 1 d PU A 1 N3 N 0.0572(17) 0.9586(14) 0.4251(8) 0.024(4) Uani 0.604(10) 1 d PDU A 1 H3 H -0.0007 1.0175 0.4136 0.029 Uiso 0.604(10) 1 d PR A 1 N4 N -0.688(2) 1.0127(13) 0.5974(8) 0.026(4) Uani 0.604(10) 1 d PU A 1 C24 C 0.2099(16) 0.8214(9) 0.3547(7) 0.008(3) Uani 0.604(10) 1 d PDU A 1 C25 C 0.2232(13) 0.9322(8) 0.3901(6) 0.011(2) Uani 0.604(10) 1 d PDU A 1 H25 H 0.3230 0.9282 0.4264 0.013 Uiso 0.604(10) 1 calc PR A 1 C26 C 0.269(2) 1.0248(14) 0.3392(9) 0.030(4) Uani 0.604(10) 1 d PDU A 1 H26A H 0.3720 0.9981 0.3117 0.036 Uiso 0.604(10) 1 calc PR A 1 H26B H 0.1639 1.0304 0.3060 0.036 Uiso 0.604(10) 1 calc PR A 1 C27 C 0.009(3) 0.9075(17) 0.4733(11) 0.036(5) Uani 0.604(10) 1 d PU A 1 C28 C -0.1848(11) 0.9301(9) 0.5076(7) 0.017(3) Uani 0.604(10) 1 d PGU A 1 C29 C -0.2966(12) 0.8454(7) 0.5297(6) 0.017(3) Uani 0.604(10) 1 d PGU A 1 H29 H -0.2581 0.7711 0.5259 0.021 Uiso 0.604(10) 1 calc PR A 1 C30 C -0.4648(12) 0.8695(7) 0.5574(6) 0.024(3) Uani 0.604(10) 1 d PGU A 1 H30 H -0.5413 0.8116 0.5725 0.029 Uiso 0.604(10) 1 calc PR A 1 C31 C -0.5212(11) 0.9782(8) 0.5630(6) 0.025(4) Uani 0.604(10) 1 d PGU A 1 C32 C -0.4094(14) 1.0629(6) 0.5409(7) 0.019(3) Uani 0.604(10) 1 d PGU A 1 H32 H -0.4479 1.1372 0.5447 0.023 Uiso 0.604(10) 1 calc PR A 1 C33 C -0.2412(14) 1.0388(8) 0.5132(7) 0.025(4) Uani 0.604(10) 1 d PGU A 1 H33A H -0.1648 1.0967 0.4981 0.030 Uiso 0.604(10) 1 calc PR A 1 O1W O 0.0330(11) 0.6963(7) -0.3826(4) 0.0160(19) Uani 0.604(10) 1 d PU A 1 H11W H 0.0620 0.6275 -0.3723 0.024 Uiso 0.604(10) 1 d PR A 1 H12W H 0.0577 0.7294 -0.4224 0.024 Uiso 0.604(10) 1 d PR A 1 O2W O 0.3304(15) 0.6092(10) -0.3220(6) 0.039(3) Uani 0.604(10) 1 d PU A 1 H21W H 0.3296 0.6845 -0.3227 0.058 Uiso 0.604(10) 1 d PR A 1 H22W H 0.4343 0.5779 -0.3321 0.058 Uiso 0.604(10) 1 d PR A 1 O3W O 0.308(3) 0.3102(19) -0.3102(10) 0.105(6) Uani 0.604(10) 1 d PU A 1 H31W H 0.3347 0.2883 -0.3432 0.158 Uiso 0.604(10) 1 d PR A 1 H32W H 0.1919 0.3074 -0.3212 0.158 Uiso 0.604(10) 1 d PR A 1 O4W O 0.4733(18) 0.3594(11) -0.1828(7) 0.068(4) Uani 0.604(10) 1 d PU A 1 H41W H 0.4091 0.3742 -0.2248 0.102 Uiso 0.604(10) 1 d PR A 1 H42W H 0.3977 0.3844 -0.1515 0.102 Uiso 0.604(10) 1 d PR A 1 O5W O -0.035(6) 0.446(4) -0.1948(19) 0.113(11) Uani 0.302(5) 1 d PU A 1 O51 O 0.060(2) 0.7860(13) 0.3454(9) 0.017(4) Uani 0.396(10) 1 d PU A 2 O61 O 0.363(3) 0.7695(18) 0.3641(11) 0.040(6) Uani 0.396(10) 1 d PU A 2 O71 O 0.256(4) 1.007(3) 0.3251(14) 0.079(8) Uani 0.396(10) 1 d PDU A 2 H71A H 0.3284 1.0373 0.2977 0.119 Uiso 0.396(10) 1 calc PR A 2 O81 O 0.060(4) 0.781(3) 0.5081(15) 0.085(9) Uani 0.396(10) 1 d PU A 2 O91 O -0.767(3) 0.921(2) 0.6320(13) 0.049(6) Uani 0.396(10) 1 d PU A 2 O101 O -0.750(3) 1.0886(19) 0.6075(13) 0.048(6) Uani 0.396(10) 1 d PU A 2 N31 N 0.071(3) 0.964(3) 0.4408(16) 0.046(10) Uani 0.396(10) 1 d PDU A 2 H31A H 0.0353 1.0301 0.4280 0.056 Uiso 0.396(10) 1 calc PR A 2 N41 N -0.677(4) 0.992(2) 0.6124(16) 0.045(6) Uani 0.396(10) 1 d PU A 2 C241 C 0.229(5) 0.807(3) 0.3739(19) 0.068(12) Uani 0.396(10) 1 d PDU A 2 C251 C 0.233(4) 0.905(2) 0.422(2) 0.086(11) Uani 0.396(10) 1 d PDU A 2 H25A H 0.3030 0.8857 0.4656 0.104 Uiso 0.396(10) 1 calc PR A 2 C261 C 0.329(5) 1.001(3) 0.3858(14) 0.082(8) Uani 0.396(10) 1 d PDU A 2 H26C H 0.3121 1.0701 0.4120 0.099 Uiso 0.396(10) 1 calc PR A 2 H26D H 0.4607 0.9858 0.3826 0.099 Uiso 0.396(10) 1 calc PR A 2 C271 C -0.017(4) 0.886(2) 0.4860(15) 0.028(7) Uani 0.396(10) 1 d PU A 2 C281 C -0.183(3) 0.918(3) 0.5192(15) 0.061(12) Uani 0.396(10) 1 d PGU A 2 C291 C -0.292(4) 0.8357(19) 0.5465(15) 0.089(14) Uani 0.396(10) 1 d PGU A 2 H29A H -0.2558 0.7608 0.5440 0.107 Uiso 0.396(10) 1 calc PR A 2 C301 C -0.455(3) 0.8632(18) 0.5775(13) 0.056(9) Uani 0.396(10) 1 d PGU A 2 H30A H -0.5297 0.8072 0.5962 0.067 Uiso 0.396(10) 1 calc PR A 2 C311 C -0.509(3) 0.973(2) 0.5812(12) 0.046(8) Uani 0.396(10) 1 d PGU A 2 C321 C -0.399(4) 1.0547(17) 0.5538(16) 0.079(14) Uani 0.396(10) 1 d PGU A 2 H32A H -0.4358 1.1295 0.5563 0.095 Uiso 0.396(10) 1 calc PR A 2 C331 C -0.237(4) 1.027(2) 0.5229(16) 0.062(12) Uani 0.396(10) 1 d PGU A 2 H331 H -0.1619 1.0832 0.5042 0.075 Uiso 0.396(10) 1 calc PR A 2 O11W O 0.056(6) 0.644(4) -0.385(2) 0.156(14) Uani 0.396(10) 1 d PU A 2 O21W O 0.369(5) 0.634(3) -0.2976(18) 0.116(11) Uani 0.396(10) 1 d PU A 2 O31W O 0.3092(14) 0.3764(10) -0.3262(6) 0.012(3) Uani 0.396(10) 1 d PU A 2 O41W O 0.248(4) 0.476(2) -0.2243(14) 0.105(8) Uani 0.396(10) 1 d PU A 2 O51W O -0.173(5) 0.458(3) -0.2021(16) 0.044(8) Uani 0.198(5) 1 d PU A 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 0.019(3) 0.030(3) 0.045(4) 0.002(3) -0.002(2) -0.002(2) O2 0.022(3) 0.033(3) 0.054(4) 0.016(3) 0.005(3) -0.003(2) O3 0.032(3) 0.018(3) 0.055(4) 0.008(3) 0.009(3) -0.005(2) O4 0.049(4) 0.039(4) 0.049(4) 0.001(3) 0.016(3) 0.003(3) N1 0.025(3) 0.025(4) 0.043(4) 0.001(3) -0.002(3) -0.001(3) N2 0.013(3) 0.039(4) 0.041(4) 0.000(3) 0.007(3) -0.002(3) C1 0.020(4) 0.025(4) 0.055(6) -0.001(4) 0.013(4) 0.004(3) C2 0.015(3) 0.039(5) 0.031(5) 0.004(4) 0.004(3) 0.005(3) C3 0.018(3) 0.026(4) 0.050(6) 0.007(4) 0.007(3) -0.002(3) C4 0.017(3) 0.019(4) 0.058(6) -0.005(4) -0.002(3) -0.002(3) C5 0.015(3) 0.028(4) 0.040(5) -0.004(4) 0.000(3) 0.001(3) C6 0.017(4) 0.031(4) 0.048(5) 0.011(4) 0.002(3) -0.001(3) C7 0.017(3) 0.024(4) 0.043(5) 0.001(4) 0.002(3) 0.006(3) C8 0.025(4) 0.014(4) 0.048(5) -0.001(3) 0.013(3) -0.001(3) C9 0.021(4) 0.031(5) 0.045(6) 0.000(4) 0.004(4) 0.000(3) C10 0.022(4) 0.033(5) 0.052(6) 0.000(4) 0.004(4) -0.006(3) C11 0.018(3) 0.020(4) 0.052(5) 0.000(4) 0.007(3) -0.004(3) C12 0.025(4) 0.022(4) 0.060(6) 0.007(4) 0.007(4) 0.001(3) C13 0.020(4) 0.028(4) 0.050(5) 0.002(4) 0.001(3) 0.002(3) C14 0.019(4) 0.032(5) 0.039(5) -0.001(4) 0.007(3) 0.008(3) C15 0.029(4) 0.038(5) 0.042(5) -0.006(4) 0.002(4) -0.003(4) C16 0.013(3) 0.036(5) 0.060(6) -0.011(4) 0.003(4) 0.001(3) C17 0.007(3) 0.029(4) 0.054(5) -0.010(4) -0.001(3) 0.005(3) C18 0.020(3) 0.020(4) 0.041(5) -0.002(4) 0.007(3) 0.000(3) C19 0.017(4) 0.041(5) 0.040(5) 0.009(4) 0.006(3) -0.001(3) C20 0.016(3) 0.020(4) 0.048(5) 0.000(3) 0.008(3) 0.006(3) C21 0.021(4) 0.031(5) 0.058(6) -0.007(4) -0.003(4) 0.004(3) C22 0.017(4) 0.045(5) 0.064(6) 0.011(5) -0.001(4) 0.000(4) C23 0.034(4) 0.024(4) 0.062(6) 0.010(4) -0.001(4) 0.002(4) O5 0.027(3) 0.027(3) 0.027(3) 0.0000(10) 0.0002(10) 0.0000(10) O6 0.015(3) 0.016(3) 0.016(3) -0.0001(10) 0.0004(10) 0.0006(10) O7 0.023(2) 0.022(2) 0.024(2) -0.0002(10) 0.0016(10) 0.0002(10) O8 0.027(3) 0.027(3) 0.027(3) 0.0008(10) 0.0012(10) 0.0005(10) O9 0.053(5) 0.053(5) 0.053(5) -0.0002(10) 0.0014(10) 0.0001(10) O10 0.049(4) 0.049(4) 0.049(4) 0.0003(10) 0.0010(10) 0.0000(10) N3 0.024(4) 0.024(4) 0.024(4) 0.0000(10) 0.0008(10) -0.0001(10) N4 0.026(4) 0.027(4) 0.026(4) -0.0001(10) 0.0007(10) -0.0003(10) C24 0.008(3) 0.008(3) 0.009(3) 0.0002(10) 0.0004(10) 0.0004(10) C25 0.011(2) 0.011(2) 0.011(2) 0.0001(10) 0.0007(10) 0.0000(10) C26 0.030(4) 0.030(4) 0.030(4) -0.0001(10) 0.0015(10) -0.0001(10) C27 0.036(5) 0.036(5) 0.036(5) 0.0003(10) 0.0004(10) 0.0001(10) C28 0.017(4) 0.017(4) 0.017(4) 0.0006(10) 0.0002(10) -0.0001(10) C29 0.017(3) 0.017(3) 0.017(3) 0.0003(10) 0.0007(10) 0.0001(10) C30 0.024(3) 0.024(3) 0.024(3) 0.0004(10) 0.0007(10) -0.0004(10) C31 0.024(4) 0.025(4) 0.024(4) -0.0001(10) 0.0009(10) 0.0000(10) C32 0.019(3) 0.019(3) 0.019(3) 0.0004(10) 0.0006(10) 0.0003(10) C33 0.026(4) 0.025(4) 0.025(4) 0.0001(10) 0.0008(10) -0.0001(10) O1W 0.016(2) 0.016(2) 0.016(2) 0.0009(10) 0.0009(10) 0.0000(10) O2W 0.038(3) 0.039(3) 0.039(3) -0.0002(10) 0.0011(10) 0.0012(10) O3W 0.105(6) 0.105(6) 0.105(6) -0.0001(10) 0.0023(11) -0.0002(10) O4W 0.068(4) 0.068(4) 0.068(4) 0.0000(10) 0.0015(10) 0.0003(10) O5W 0.113(11) 0.113(11) 0.113(11) -0.0001(10) 0.0026(11) 0.0000(10) O51 0.017(4) 0.017(4) 0.017(4) 0.0002(10) 0.0008(10) -0.0003(10) O61 0.040(6) 0.040(6) 0.040(6) 0.0001(10) 0.0010(11) 0.0003(10) O71 0.079(8) 0.079(8) 0.079(8) 0.0000(10) 0.0020(11) -0.0002(10) O81 0.085(9) 0.085(9) 0.085(9) 0.0000(10) 0.0020(11) 0.0001(10) O91 0.049(6) 0.049(6) 0.049(6) 0.0000(10) 0.0013(10) 0.0000(10) O101 0.048(6) 0.048(6) 0.048(6) -0.0002(10) 0.0013(11) -0.0002(10) N31 0.046(10) 0.047(10) 0.047(10) -0.0001(10) 0.0012(11) 0.0001(10) N41 0.045(6) 0.045(6) 0.045(6) 0.0003(10) 0.0011(10) 0.0000(10) C241 0.068(12) 0.068(12) 0.068(12) 0.0000(10) 0.0016(11) 0.0000(10) C251 0.086(11) 0.086(11) 0.086(11) -0.0001(10) 0.0020(11) 0.0001(10) C261 0.082(8) 0.082(8) 0.082(8) 0.0000(10) 0.0020(11) -0.0001(10) C271 0.028(7) 0.028(7) 0.028(7) -0.0002(10) 0.0007(11) -0.0002(10) C281 0.061(12) 0.061(12) 0.061(12) 0.0001(10) 0.0013(11) 0.0001(10) C291 0.089(14) 0.089(14) 0.089(14) 0.0000(10) 0.0021(11) 0.0000(10) C301 0.056(9) 0.056(9) 0.056(9) 0.0000(10) 0.0012(11) -0.0001(10) C311 0.046(8) 0.046(8) 0.046(8) 0.0001(10) 0.0010(11) 0.0001(10) C321 0.079(14) 0.079(14) 0.079(14) 0.0000(10) 0.0019(11) 0.0001(10) C331 0.062(12) 0.062(12) 0.062(12) 0.0000(10) 0.0015(11) 0.0000(10) O11W 0.156(14) 0.156(14) 0.156(14) 0.0000(10) 0.0036(11) 0.0000(10) O21W 0.116(11) 0.116(11) 0.116(11) -0.0002(10) 0.0027(11) 0.0001(10) O31W 0.012(3) 0.012(3) 0.012(3) 0.0005(10) 0.0003(10) 0.0000(10) O41W 0.105(9) 0.105(9) 0.105(9) -0.0001(10) 0.0024(11) 0.0000(10) O51W 0.044(8) 0.044(8) 0.044(8) 0.0000(10) 0.0010(11) 0.0000(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 C12 1.378(10) . ? O1 C11 1.448(9) . ? O2 C2 1.333(9) . ? O2 C22 1.430(11) . ? O3 C23 1.415(11) . ? O3 C3 1.437(10) . ? O4 C9 1.206(10) . ? N1 C9 1.390(11) . ? N1 C6 1.433(10) . ? N1 C8 1.472(11) . ? N2 C15 1.503(12) . ? N2 C16 1.520(10) . ? N2 C21 1.548(11) . ? N2 H2 0.9300 . ? C1 C6 1.408(12) . ? C1 C2 1.422(12) . ? C1 H1 0.9500 . ? C2 C3 1.365(12) . ? C3 C4 1.367(12) . ? C4 C5 1.424(11) . ? C4 H4 0.9500 . ? C5 C6 1.346(12) . ? C5 C7 1.465(11) . ? C7 C8 1.552(11) . ? C7 C21 1.557(12) . ? C7 C17 1.564(10) . ? C8 C18 1.524(11) . ? C8 H8 1.0000 . ? C9 C10 1.520(12) . ? C10 C11 1.530(12) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C18 1.547(11) . ? C11 H11 1.0000 . ? C12 C13 1.540(12) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.333(12) . ? C13 H13 0.9500 . ? C14 C15 1.512(12) . ? C14 C19 1.514(10) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 C17 1.509(12) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 C19 1.538(12) . ? C18 H18 1.0000 . ? C19 C20 1.512(12) . ? C19 H19 1.0000 . ? C20 C21 1.526(10) . ? 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 1.293(16) . ? O6 C24 1.262(14) . ? O7 C26 1.270(18) . ? O7 H7 0.8400 . ? O8 C27 1.28(2) . ? O9 N4 1.40(2) . ? O10 N4 1.105(19) . ? N3 C27 1.17(3) . ? N3 C25 1.444(13) . ? N3 H3 0.8596 . ? N4 C31 1.470(17) . ? C24 C25 1.509(13) . ? C25 C26 1.53(2) . ? C25 H25 1.0000 . ? C26 H26A 0.9900 . ? C26 H26B 0.9900 . ? C27 C28 1.61(2) . ? C28 C29 1.3900 . ? C28 C33 1.3900 . ? C29 C30 1.3900 . ? C29 H29 0.9500 . ? C30 C31 1.3900 . ? C30 H30 0.9500 . ? C31 C32 1.3900 . ? C32 C33 1.3900 . ? C32 H32 0.9500 . ? C33 H33A 0.9500 . ? O1W H11W 0.8832 . ? O1W H12W 0.8815 . ? O2W H21W 0.9161 . ? O2W H22W 0.8800 . ? O3W H31W 0.7146 . ? O3W H32W 0.8800 . ? O4W H41W 0.9402 . ? O4W H42W 0.8800 . ? O51 C241 1.37(4) . ? O61 C241 1.11(4) . ? O71 C261 1.270(19) . ? O71 H71A 0.8400 . ? O81 C271 1.47(4) . ? O91 N41 1.16(4) . ? O101 N41 1.29(4) . ? N31 C271 1.44(4) . ? N31 C251 1.443(14) . ? N31 H3 0.9805 . ? N31 H31A 0.8800 . ? N41 C311 1.41(3) . ? C241 C251 1.507(13) . ? C251 C261 1.53(2) . ? C251 H25A 1.0000 . ? C261 H26C 0.9900 . ? C261 H26D 0.9900 . ? C271 C281 1.44(3) . ? C281 C291 1.3900 . ? C281 C331 1.3900 . ? C291 C301 1.3900 . ? C291 H29A 0.9500 . ? C301 C311 1.3900 . ? C301 H30A 0.9500 . ? C311 C321 1.3900 . ? C321 C331 1.3900 . ? C321 H32A 0.9500 . ? C331 H331 0.9500 . ? O11W H11W 0.3194 . ? O11W H12W 1.2594 . ? O21W H21W 0.8301 . ? O21W H22W 1.0679 . ? O31W H31W 1.1352 . ? O31W H32W 1.2094 . ? 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 115.7(6) . . ? C2 O2 C22 118.9(7) . . ? C23 O3 C3 117.5(6) . . ? C9 N1 C6 123.7(7) . . ? C9 N1 C8 122.1(7) . . ? C6 N1 C8 108.3(6) . . ? C15 N2 C16 111.8(6) . . ? C15 N2 C21 114.3(6) . . ? C16 N2 C21 106.8(6) . . ? C15 N2 H2 107.9 . . ? C16 N2 H2 107.9 . . ? C21 N2 H2 107.9 . . ? C6 C1 C2 116.9(8) . . ? C6 C1 H1 121.5 . . ? C2 C1 H1 121.5 . . ? O2 C2 C3 120.1(8) . . ? O2 C2 C1 121.8(8) . . ? C3 C2 C1 118.0(8) . . ? C2 C3 C4 124.9(8) . . ? C2 C3 O3 113.0(7) . . ? C4 C3 O3 122.1(8) . . ? C3 C4 C5 117.2(8) . . ? C3 C4 H4 121.4 . . ? C5 C4 H4 121.4 . . ? C6 C5 C4 119.0(8) . . ? C6 C5 C7 111.4(7) . . ? C4 C5 C7 129.3(8) . . ? C5 C6 C1 123.7(8) . . ? C5 C6 N1 109.9(7) . . ? C1 C6 N1 126.4(8) . . ? C5 C7 C8 102.7(6) . . ? C5 C7 C21 115.7(7) . . ? C8 C7 C21 114.9(7) . . ? C5 C7 C17 113.2(6) . . ? C8 C7 C17 110.3(6) . . ? C21 C7 C17 100.5(6) . . ? N1 C8 C18 106.4(6) . . ? N1 C8 C7 103.9(6) . . ? C18 C8 C7 116.7(7) . . ? N1 C8 H8 109.9 . . ? C18 C8 H8 109.9 . . ? C7 C8 H8 109.9 . . ? O4 C9 N1 122.5(8) . . ? O4 C9 C10 123.2(8) . . ? N1 C9 C10 114.3(8) . . ? C9 C10 C11 119.4(7) . . ? C9 C10 H10A 107.5 . . ? C11 C10 H10A 107.5 . . ? C9 C10 H10B 107.5 . . ? C11 C10 H10B 107.5 . . ? H10A C10 H10B 107.0 . . ? O1 C11 C10 107.0(6) . . ? O1 C11 C18 112.6(6) . . ? C10 C11 C18 110.8(7) . . ? O1 C11 H11 108.8 . . ? C10 C11 H11 108.8 . . ? C18 C11 H11 108.8 . . ? O1 C12 C13 112.5(6) . . ? O1 C12 H12A 109.1 . . ? C13 C12 H12A 109.1 . . ? O1 C12 H12B 109.1 . . ? C13 C12 H12B 109.1 . . ? H12A C12 H12B 107.8 . . ? C14 C13 C12 120.6(7) . . ? C14 C13 H13 119.7 . . ? C12 C13 H13 119.7 . . ? C13 C14 C15 119.8(7) . . ? C13 C14 C19 125.2(7) . . ? C15 C14 C19 114.9(7) . . ? N2 C15 C14 110.5(7) . . ? N2 C15 H15A 109.6 . . ? C14 C15 H15A 109.6 . . ? N2 C15 H15B 109.6 . . ? C14 C15 H15B 109.6 . . ? H15A C15 H15B 108.1 . . ? C17 C16 N2 105.1(6) . . ? C17 C16 H16A 110.7 . . ? N2 C16 H16A 110.7 . . ? C17 C16 H16B 110.7 . . ? N2 C16 H16B 110.7 . . ? H16A C16 H16B 108.8 . . ? C16 C17 C7 103.0(6) . . ? 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 C19 112.0(6) . . ? C8 C18 C11 107.2(6) . . ? C19 C18 C11 119.0(7) . . ? C8 C18 H18 105.9 . . ? C19 C18 H18 105.9 . . ? C11 C18 H18 105.9 . . ? C20 C19 C14 110.4(7) . . ? C20 C19 C18 106.6(7) . . ? C14 C19 C18 114.1(6) . . ? C20 C19 H19 108.5 . . ? C14 C19 H19 108.5 . . ? C18 C19 H19 108.5 . . ? C19 C20 C21 110.0(7) . . ? C19 C20 H20A 109.7 . . ? C21 C20 H20A 109.7 . . ? C19 C20 H20B 109.7 . . ? C21 C20 H20B 109.7 . . ? H20A C20 H20B 108.2 . . ? C20 C21 N2 109.2(7) . . ? C20 C21 C7 113.5(7) . . ? N2 C21 C7 104.9(6) . . ? C20 C21 H21 109.7 . . ? N2 C21 H21 109.7 . . ? C7 C21 H21 109.7 . . ? 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 . . ? C26 O7 H7 109.5 . . ? C27 N3 C25 121.4(15) . . ? C27 N3 H3 119.0 . . ? C25 N3 H3 119.2 . . ? O10 N4 O9 127.6(16) . . ? O10 N4 C31 120.8(15) . . ? O9 N4 C31 111.6(13) . . ? O6 C24 O5 123.1(11) . . ? O6 C24 C25 120.4(10) . . ? O5 C24 C25 115.4(10) . . ? N3 C25 C24 111.1(10) . . ? N3 C25 C26 109.3(12) . . ? C24 C25 C26 112.6(10) . . ? N3 C25 H25 107.9 . . ? C24 C25 H25 107.9 . . ? C26 C25 H25 107.9 . . ? O7 C26 C25 124.5(13) . . ? O7 C26 H26A 106.2 . . ? C25 C26 H26A 106.2 . . ? O7 C26 H26B 106.2 . . ? C25 C26 H26B 106.2 . . ? H26A C26 H26B 106.4 . . ? N3 C27 O8 127.3(18) . . ? N3 C27 C28 121.1(16) . . ? O8 C27 C28 110.6(17) . . ? C29 C28 C33 120.0 . . ? C29 C28 C27 122.4(10) . . ? C33 C28 C27 117.6(10) . . ? C28 C29 C30 120.0 . . ? C28 C29 H29 120.0 . . ? C30 C29 H29 120.0 . . ? C31 C30 C29 120.0 . . ? C31 C30 H30 120.0 . . ? C29 C30 H30 120.0 . . ? C32 C31 C30 120.0 . . ? C32 C31 N4 115.7(9) . . ? C30 C31 N4 124.1(9) . . ? C31 C32 C33 120.0 . . ? C31 C32 H32 120.0 . . ? C33 C32 H32 120.0 . . ? C32 C33 C28 120.0 . . ? C32 C33 H33A 120.0 . . ? C28 C33 H33A 120.0 . . ? H11W O1W H12W 124.8 . . ? H21W O2W H22W 115.7 . . ? H31W O3W H32W 93.4 . . ? H41W O4W H42W 101.5 . . ? C261 O71 H71A 109.5 . . ? C271 N31 C251 102(3) . . ? C271 N31 H3 120.3 . . ? C251 N31 H3 129.4 . . ? C271 N31 H31A 128.8 . . ? C251 N31 H31A 128.8 . . ? H3 N31 H31A 24.5 . . ? O91 N41 O101 118(3) . . ? O91 N41 C311 121(3) . . ? O101 N41 C311 119(3) . . ? O61 C241 O51 132(3) . . ? O61 C241 C251 115(3) . . ? O51 C241 C251 113(3) . . ? N31 C251 C241 123(3) . . ? N31 C251 C261 98(3) . . ? C241 C251 C261 109(3) . . ? N31 C251 H25A 108.8 . . ? C241 C251 H25A 108.8 . . ? C261 C251 H25A 108.8 . . ? O71 C261 C251 106(3) . . ? O71 C261 H26C 110.6 . . ? C251 C261 H26C 110.6 . . ? O71 C261 H26D 110.6 . . ? C251 C261 H26D 110.6 . . ? H26C C261 H26D 108.8 . . ? C281 C271 N31 119(2) . . ? C281 C271 O81 116(3) . . ? N31 C271 O81 125(2) . . ? C291 C281 C331 120.0 . . ? C291 C281 C271 119(2) . . ? C331 C281 C271 121(2) . . ? C281 C291 C301 120.0 . . ? C281 C291 H29A 120.0 . . ? C301 C291 H29A 120.0 . . ? C291 C301 C311 120.0 . . ? C291 C301 H30A 120.0 . . ? C311 C301 H30A 120.0 . . ? C321 C311 C301 120.0 . . ? C321 C311 N41 124(2) . . ? C301 C311 N41 116(2) . . ? C311 C321 C331 120.0 . . ? C311 C321 H32A 120.0 . . ? C331 C321 H32A 120.0 . . ? C321 C331 C281 120.0 . . ? C321 C331 H331 120.0 . . ? C281 C331 H331 120.0 . . ? H11W O11W H12W 160.3 . . ? H21W O21W H22W 105.9 . . ? H31W O31W H32W 59.5 . . ? 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 C3 177.3(6) . . . . ? C22 O2 C2 C1 -2.7(10) . . . . ? C6 C1 C2 O2 -178.1(6) . . . . ? C6 C1 C2 C3 1.9(10) . . . . ? O2 C2 C3 C4 175.5(7) . . . . ? C1 C2 C3 C4 -4.6(11) . . . . ? O2 C2 C3 O3 -5.2(10) . . . . ? C1 C2 C3 O3 174.8(6) . . . . ? C23 O3 C3 C2 -177.5(7) . . . . ? C23 O3 C3 C4 1.8(10) . . . . ? C2 C3 C4 C5 3.4(11) . . . . ? O3 C3 C4 C5 -175.9(7) . . . . ? C3 C4 C5 C6 0.5(10) . . . . ? C3 C4 C5 C7 -172.8(7) . . . . ? C4 C5 C6 C1 -3.1(11) . . . . ? C7 C5 C6 C1 171.4(7) . . . . ? C4 C5 C6 N1 174.7(6) . . . . ? C7 C5 C6 N1 -10.8(9) . . . . ? C2 C1 C6 C5 1.8(11) . . . . ? C2 C1 C6 N1 -175.6(7) . . . . ? C9 N1 C6 C5 -155.8(7) . . . . ? C8 N1 C6 C5 -2.4(8) . . . . ? C9 N1 C6 C1 22.0(12) . . . . ? C8 N1 C6 C1 175.3(7) . . . . ? C6 C5 C7 C8 18.5(8) . . . . ? C4 C5 C7 C8 -167.8(8) . . . . ? C6 C5 C7 C21 144.4(7) . . . . ? C4 C5 C7 C21 -41.9(11) . . . . ? C6 C5 C7 C17 -100.4(8) . . . . ? C4 C5 C7 C17 73.3(10) . . . . ? C9 N1 C8 C18 43.6(9) . . . . ? C6 N1 C8 C18 -110.3(7) . . . . ? C9 N1 C8 C7 167.3(6) . . . . ? C6 N1 C8 C7 13.4(8) . . . . ? C5 C7 C8 N1 -18.6(7) . . . . ? C21 C7 C8 N1 -145.0(6) . . . . ? C17 C7 C8 N1 102.3(7) . . . . ? C5 C7 C8 C18 98.1(8) . . . . ? C21 C7 C8 C18 -28.3(10) . . . . ? C17 C7 C8 C18 -141.0(7) . . . . ? C6 N1 C9 O4 -24.6(12) . . . . ? C8 N1 C9 O4 -174.4(7) . . . . ? C6 N1 C9 C10 154.4(7) . . . . ? C8 N1 C9 C10 4.5(10) . . . . ? O4 C9 C10 C11 151.7(8) . . . . ? N1 C9 C10 C11 -27.3(10) . . . . ? C12 O1 C11 C10 168.1(6) . . . . ? C12 O1 C11 C18 -70.0(8) . . . . ? C9 C10 C11 O1 122.0(7) . . . . ? C9 C10 C11 C18 -1.0(9) . . . . ? C11 O1 C12 C13 89.2(7) . . . . ? O1 C12 C13 C14 -62.3(10) . . . . ? C12 C13 C14 C15 173.9(7) . . . . ? C12 C13 C14 C19 -4.1(13) . . . . ? C16 N2 C15 C14 75.6(8) . . . . ? C21 N2 C15 C14 -45.8(9) . . . . ? C13 C14 C15 N2 -125.9(8) . . . . ? C19 C14 C15 N2 52.3(9) . . . . ? C15 N2 C16 C17 -142.8(7) . . . . ? C21 N2 C16 C17 -17.1(8) . . . . ? N2 C16 C17 C7 38.5(8) . . . . ? C5 C7 C17 C16 -168.3(7) . . . . ? C8 C7 C17 C16 77.3(8) . . . . ? C21 C7 C17 C16 -44.3(8) . . . . ? N1 C8 C18 C19 158.0(6) . . . . ? C7 C8 C18 C19 42.7(9) . . . . ? N1 C8 C18 C11 -69.8(7) . . . . ? C7 C8 C18 C11 174.9(7) . . . . ? O1 C11 C18 C8 -71.2(8) . . . . ? C10 C11 C18 C8 48.6(8) . . . . ? O1 C11 C18 C19 57.1(8) . . . . ? C10 C11 C18 C19 176.9(6) . . . . ? C13 C14 C19 C20 176.6(8) . . . . ? C15 C14 C19 C20 -1.5(10) . . . . ? C13 C14 C19 C18 56.6(11) . . . . ? C15 C14 C19 C18 -121.4(8) . . . . ? C8 C18 C19 C20 -61.9(8) . . . . ? C11 C18 C19 C20 172.0(6) . . . . ? C8 C18 C19 C14 60.2(9) . . . . ? C11 C18 C19 C14 -65.9(9) . . . . ? C14 C19 C20 C21 -55.6(9) . . . . ? C18 C19 C20 C21 68.8(8) . . . . ? C19 C20 C21 N2 61.0(9) . . . . ? C19 C20 C21 C7 -55.6(9) . . . . ? C15 N2 C21 C20 -8.8(9) . . . . ? C16 N2 C21 C20 -133.0(7) . . . . ? C15 N2 C21 C7 113.2(7) . . . . ? C16 N2 C21 C7 -11.0(8) . . . . ? C5 C7 C21 C20 -85.3(9) . . . . ? C8 C7 C21 C20 34.2(10) . . . . ? C17 C7 C21 C20 152.6(7) . . . . ? C5 C7 C21 N2 155.6(6) . . . . ? C8 C7 C21 N2 -85.0(7) . . . . ? C17 C7 C21 N2 33.4(8) . . . . ? C27 N3 C25 C24 66(2) . . . . ? C27 N3 C25 C26 -169.3(18) . . . . ? O6 C24 C25 N3 -155.4(13) . . . . ? O5 C24 C25 N3 36.8(16) . . . . ? O6 C24 C25 C26 81.6(16) . . . . ? O5 C24 C25 C26 -86.2(14) . . . . ? N3 C25 C26 O7 64.6(18) . . . . ? C24 C25 C26 O7 -171.5(13) . . . . ? C25 N3 C27 O8 -7(3) . . . . ? C25 N3 C27 C28 -174.2(13) . . . . ? N3 C27 C28 C29 139.1(18) . . . . ? O8 C27 C28 C29 -30.1(19) . . . . ? N3 C27 C28 C33 -39(2) . . . . ? O8 C27 C28 C33 151.5(12) . . . . ? C33 C28 C29 C30 0.0 . . . . ? C27 C28 C29 C30 -178.4(13) . . . . ? C28 C29 C30 C31 0.0 . . . . ? C29 C30 C31 C32 0.0 . . . . ? C29 C30 C31 N4 -174.1(12) . . . . ? O10 N4 C31 C32 33.0(19) . . . . ? O9 N4 C31 C32 -148.1(11) . . . . ? O10 N4 C31 C30 -152.7(14) . . . . ? O9 N4 C31 C30 26.2(17) . . . . ? C30 C31 C32 C33 0.0 . . . . ? N4 C31 C32 C33 174.6(11) . . . . ? C31 C32 C33 C28 0.0 . . . . ? C29 C28 C33 C32 0.0 . . . . ? C27 C28 C33 C32 178.5(12) . . . . ? C271 N31 C251 C241 71(4) . . . . ? C271 N31 C251 C261 -171(2) . . . . ? O61 C241 C251 N31 -180(3) . . . . ? O51 C241 C251 N31 6(5) . . . . ? O61 C241 C251 C261 67(4) . . . . ? O51 C241 C251 C261 -107(3) . . . . ? N31 C251 C261 O71 -79(3) . . . . ? C241 C251 C261 O71 49(4) . . . . ? C251 N31 C271 C281 177(3) . . . . ? C251 N31 C271 O81 5(4) . . . . ? N31 C271 C281 C291 163(2) . . . . ? O81 C271 C281 C291 -24(3) . . . . ? N31 C271 C281 C331 -16(3) . . . . ? O81 C271 C281 C331 157(2) . . . . ? C331 C281 C291 C301 0.0 . . . . ? C271 C281 C291 C301 -179(3) . . . . ? C281 C291 C301 C311 0.0 . . . . ? C291 C301 C311 C321 0.0 . . . . ? C291 C301 C311 N41 179(2) . . . . ? O91 N41 C311 C321 177(3) . . . . ? O101 N41 C311 C321 10(4) . . . . ? O91 N41 C311 C301 -2(4) . . . . ? O101 N41 C311 C301 -169(2) . . . . ? C301 C311 C321 C331 0.0 . . . . ? N41 C311 C321 C331 -179(3) . . . . ? C311 C321 C331 C281 0.0 . . . . ? C291 C281 C331 C321 0.0 . . . . ? C271 C281 C331 C321 179(3) . . . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 28.00 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.428 _refine_diff_density_min -0.437 _refine_diff_density_rms 0.091 # start Validation Reply Form _vrf_PLAT430_8 ; PROBLEM: Short Inter D...A Contact O31W .. O41W .. 2.34 Ang. RESPONSE: disordered water molecules ; # end Validation Reply Form #===== end data_9 _database_code_depnum_ccdc_archive 'CCDC 758150' #TrackingRef 'bialonska2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; brucinium N-(4-nitrobenzoyl)-L-serinate tetrahydrate ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C23 H27 N2 O4, C10 H9 N2 O6, 4(H2 O)' _chemical_formula_sum 'C33 H44 N4 O14' _chemical_formula_weight 720.72 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting 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 7.996(3) _cell_length_b 33.138(5) _cell_length_c 12.679(3) _cell_angle_alpha 90.00 _cell_angle_beta 93.59(3) _cell_angle_gamma 90.00 _cell_volume 3353.0(16) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6385 _cell_measurement_theta_min 3.10 _cell_measurement_theta_max 28.42 _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.428 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1528 _exptl_absorpt_coefficient_mu 0.112 _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 20807 _diffrn_reflns_av_R_equivalents 0.0440 _diffrn_reflns_av_sigmaI/netI 0.0485 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -42 _diffrn_reflns_limit_k_max 42 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.10 _diffrn_reflns_theta_max 27.00 _reflns_number_total 7427 _reflns_number_gt 5986 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET) (compiled May 8 2007,13:10:02) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET) (compiled May 8 2007,13:10:02) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET) (compiled May 8 2007,13:10:02) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0783P)^2^+2.2454P] 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 7427 _refine_ls_number_parameters 1127 _refine_ls_number_restraints 134 _refine_ls_R_factor_all 0.0725 _refine_ls_R_factor_gt 0.0587 _refine_ls_wR_factor_ref 0.1566 _refine_ls_wR_factor_gt 0.1493 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.044 _refine_ls_shift/su_max 0.003 _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 0.0641(3) 0.33433(8) 0.57336(19) 0.0298(6) Uani 1 1 d . . . O2 O -0.0214(3) 0.19877(7) -0.01346(19) 0.0291(6) Uani 1 1 d . . . O3 O 0.0265(3) 0.26493(8) -0.11489(18) 0.0288(6) Uani 1 1 d . . . O4 O -0.0147(4) 0.21447(8) 0.3820(2) 0.0378(7) Uani 1 1 d . . . N1 N -0.0255(3) 0.27863(9) 0.3178(2) 0.0227(6) Uani 1 1 d . . . N2 N 0.0334(5) 0.41524(10) 0.2471(3) 0.0397(9) Uani 1 1 d . . . H2 H 0.0328 0.4339 0.1924 0.048 Uiso 1 1 calc R . . C1 C -0.0291(4) 0.23322(11) 0.1558(3) 0.0242(7) Uani 1 1 d . . . H1 H -0.0461 0.2089 0.1935 0.029 Uiso 1 1 calc R . . C2 C -0.0141(4) 0.23297(11) 0.0467(3) 0.0251(8) Uani 1 1 d . . . C3 C 0.0111(4) 0.26944(11) -0.0088(3) 0.0230(7) Uani 1 1 d . . . C4 C 0.0177(4) 0.30583(11) 0.0451(3) 0.0267(8) Uani 1 1 d . . . H4 H 0.0322 0.3303 0.0077 0.032 Uiso 1 1 calc R . . C5 C 0.0030(4) 0.30661(11) 0.1539(3) 0.0235(8) Uani 1 1 d . . . C6 C -0.0180(4) 0.27080(11) 0.2081(3) 0.0237(7) Uani 1 1 d . . . C7 C -0.0068(5) 0.34227(11) 0.2266(3) 0.0262(8) Uani 1 1 d . . . C8 C 0.0089(4) 0.32236(10) 0.3370(3) 0.0241(8) Uani 1 1 d . . . H8 H -0.0784 0.3338 0.3816 0.029 Uiso 1 1 calc R . . C9 C 0.0033(5) 0.25120(11) 0.3970(3) 0.0284(8) Uani 1 1 d . . . C10 C 0.0581(5) 0.26776(12) 0.5042(3) 0.0324(9) Uani 1 1 d . . . H10A H 0.1278 0.2470 0.5419 0.039 Uiso 1 1 calc R . . H10B H -0.0433 0.2715 0.5441 0.039 Uiso 1 1 calc R . . C11 C 0.1575(5) 0.30795(12) 0.5098(3) 0.0298(9) Uani 1 1 d . . . H11 H 0.2704 0.3031 0.5460 0.036 Uiso 1 1 calc R . . C12 C 0.1460(6) 0.37123(14) 0.6052(3) 0.0418(11) Uani 1 1 d . . . H12A H 0.2680 0.3664 0.6161 0.050 Uiso 1 1 calc R . . H12B H 0.1046 0.3802 0.6734 0.050 Uiso 1 1 calc R . . C13 C 0.1155(6) 0.40424(13) 0.5242(4) 0.0400(10) Uani 1 1 d . . . H13 H 0.0584 0.4280 0.5439 0.048 Uiso 1 1 calc R . . C14 C 0.1651(5) 0.40143(13) 0.4271(3) 0.0367(10) Uani 1 1 d . . . C15 C 0.1226(7) 0.43403(13) 0.3444(4) 0.0465(12) Uani 1 1 d . . . H15A H 0.0497 0.4547 0.3743 0.056 Uiso 1 1 calc R . . H15B H 0.2267 0.4474 0.3245 0.056 Uiso 1 1 calc R . . C16 C -0.1467(6) 0.40429(12) 0.2656(3) 0.0367(10) Uani 1 1 d . . . H16A H -0.1622 0.4009 0.3420 0.044 Uiso 1 1 calc R . . H16B H -0.2246 0.4254 0.2370 0.044 Uiso 1 1 calc R . . C17 C -0.1759(5) 0.36523(12) 0.2078(3) 0.0325(9) Uani 1 1 d . . . H17A H -0.2024 0.3700 0.1315 0.039 Uiso 1 1 calc R . . H17B H -0.2688 0.3499 0.2369 0.039 Uiso 1 1 calc R . . C18 C 0.1798(4) 0.32446(11) 0.3979(3) 0.0259(8) Uani 1 1 d . . . H18 H 0.2530 0.3047 0.3631 0.031 Uiso 1 1 calc R . . C19 C 0.2642(5) 0.36569(13) 0.3884(3) 0.0352(9) Uani 1 1 d . . . H19 H 0.3765 0.3650 0.4278 0.042 Uiso 1 1 calc R . . C20 C 0.2888(5) 0.37130(13) 0.2681(3) 0.0389(10) Uani 1 1 d . . . H20A H 0.3593 0.3953 0.2570 0.047 Uiso 1 1 calc R . . H20B H 0.3459 0.3474 0.2403 0.047 Uiso 1 1 calc R . . C21 C 0.1202(5) 0.37652(11) 0.2110(3) 0.0311(9) Uani 1 1 d . . . H21 H 0.1367 0.3790 0.1337 0.037 Uiso 1 1 calc R . . C22 C -0.0302(6) 0.16101(12) 0.0419(3) 0.0381(10) Uani 1 1 d . . . H22A H -0.0348 0.1388 -0.0091 0.057 Uiso 1 1 calc R . . H22B H -0.1311 0.1606 0.0820 0.057 Uiso 1 1 calc R . . H22C H 0.0692 0.1580 0.0906 0.057 Uiso 1 1 calc R . . C23 C 0.0535(5) 0.30151(12) -0.1735(3) 0.0310(9) Uani 1 1 d . . . H23A H 0.0632 0.2949 -0.2482 0.047 Uiso 1 1 calc R . . H23B H 0.1568 0.3146 -0.1455 0.047 Uiso 1 1 calc R . . H23C H -0.0414 0.3199 -0.1667 0.047 Uiso 1 1 calc R . . O1A O 0.4505(3) 0.72722(9) -0.05233(19) 0.0366(7) Uani 1 1 d . . . O2A O 0.3395(3) 0.86601(8) 0.52118(19) 0.0283(6) Uani 1 1 d . . . O3A O 0.4011(3) 0.80110(8) 0.63072(18) 0.0277(6) Uani 1 1 d . . . O4A O 0.3589(4) 0.84721(9) 0.1287(2) 0.0427(8) Uani 1 1 d . . . N1A N 0.3530(4) 0.78391(10) 0.1947(2) 0.0285(7) Uani 1 1 d . . . N2A N 0.4280(4) 0.64858(11) 0.2771(3) 0.0346(8) Uani 1 1 d . . . H2A H 0.4330 0.6301 0.3323 0.041 Uiso 1 1 calc R . . C1A C 0.3421(4) 0.83020(12) 0.3528(3) 0.0276(8) Uani 1 1 d . . . H1A H 0.3236 0.8541 0.3123 0.033 Uiso 1 1 calc R . . C2A C 0.3540(4) 0.83115(11) 0.4636(3) 0.0261(8) Uani 1 1 d . . . C3A C 0.3857(4) 0.79589(12) 0.5246(3) 0.0262(8) Uani 1 1 d . . . C4A C 0.3976(4) 0.75879(11) 0.4728(3) 0.0257(8) Uani 1 1 d . . . H4A H 0.4155 0.7346 0.5123 0.031 Uiso 1 1 calc R . . C5A C 0.3829(4) 0.75757(12) 0.3618(3) 0.0277(8) Uani 1 1 d . . . C6A C 0.3587(4) 0.79262(12) 0.3045(3) 0.0271(8) Uani 1 1 d . . . C7A C 0.3762(5) 0.72116(12) 0.2901(3) 0.0277(8) Uani 1 1 d . . . C8A C 0.3909(4) 0.74021(12) 0.1793(3) 0.0276(8) Uani 1 1 d . . . H8A H 0.3048 0.7281 0.1281 0.033 Uiso 1 1 calc R . . C9A C 0.3801(5) 0.81072(13) 0.1162(3) 0.0324(9) Uani 1 1 d . . . C10A C 0.4349(5) 0.79314(13) 0.0131(3) 0.0338(9) Uani 1 1 d . . . H10C H 0.4998 0.8141 -0.0220 0.041 Uiso 1 1 calc R . . H10D H 0.3328 0.7878 -0.0330 0.041 Uiso 1 1 calc R . . C11A C 0.5398(5) 0.75447(14) 0.0184(3) 0.0345(10) Uani 1 1 d . . . H11A H 0.6521 0.7602 -0.0088 0.041 Uiso 1 1 calc R . . C12A C 0.5395(6) 0.69042(15) -0.0727(3) 0.0462(12) Uani 1 1 d . . . H12C H 0.6612 0.6961 -0.0706 0.055 Uiso 1 1 calc R . . H12D H 0.5046 0.6806 -0.1445 0.055 Uiso 1 1 calc R . . C13A C 0.5069(5) 0.65826(14) 0.0063(3) 0.0378(10) Uani 1 1 d . . . H13A H 0.4494 0.6345 -0.0172 0.045 Uiso 1 1 calc R . . C14A C 0.5558(5) 0.66168(13) 0.1088(3) 0.0351(9) Uani 1 1 d . . . C15A C 0.5178(5) 0.63043(13) 0.1867(3) 0.0355(10) Uani 1 1 d . . . H15C H 0.6234 0.6176 0.2147 0.043 Uiso 1 1 calc R . . H15D H 0.4467 0.6093 0.1518 0.043 Uiso 1 1 calc R . . C16A C 0.2442(5) 0.65711(13) 0.2468(3) 0.0365(10) Uani 1 1 d . . . H16C H 0.1718 0.6360 0.2750 0.044 Uiso 1 1 calc R . . H16D H 0.2238 0.6583 0.1691 0.044 Uiso 1 1 calc R . . C17A C 0.2104(5) 0.69806(13) 0.2969(3) 0.0315(9) Uani 1 1 d . . . H17C H 0.1819 0.6948 0.3713 0.038 Uiso 1 1 calc R . . H17D H 0.1174 0.7123 0.2573 0.038 Uiso 1 1 calc R . . C18A C 0.5634(5) 0.73878(13) 0.1327(3) 0.0311(9) Uani 1 1 d . . . H18A H 0.6332 0.7595 0.1724 0.037 Uiso 1 1 calc R . . C19A C 0.6521(5) 0.69867(14) 0.1535(3) 0.0336(9) Uani 1 1 d . . . H19A H 0.7643 0.6997 0.1228 0.040 Uiso 1 1 calc R . . C20A C 0.6774(5) 0.69416(14) 0.2736(3) 0.0342(9) Uani 1 1 d . . . H20C H 0.7506 0.6707 0.2913 0.041 Uiso 1 1 calc R . . H20D H 0.7319 0.7186 0.3045 0.041 Uiso 1 1 calc R . . C21A C 0.5082(5) 0.68814(12) 0.3185(3) 0.0310(9) Uani 1 1 d . . . H21A H 0.5247 0.6864 0.3972 0.037 Uiso 1 1 calc R . . C22A C 0.3406(5) 0.90334(12) 0.4627(3) 0.0350(9) Uani 1 1 d . . . H22D H 0.3292 0.9261 0.5111 0.053 Uiso 1 1 calc R . . H22E H 0.2470 0.9035 0.4090 0.053 Uiso 1 1 calc R . . H22F H 0.4465 0.9058 0.4282 0.053 Uiso 1 1 calc R . . C23A C 0.4338(5) 0.76532(12) 0.6944(3) 0.0308(9) Uani 1 1 d . . . H23D H 0.4423 0.7728 0.7693 0.046 Uiso 1 1 calc R . . H23E H 0.5392 0.7530 0.6755 0.046 Uiso 1 1 calc R . . H23F H 0.3419 0.7460 0.6813 0.046 Uiso 1 1 calc R . . O5A O 0.5703(8) 0.59755(17) 0.4172(4) 0.0395(14) Uani 0.639(2) 1 d PU A 1 O6A O 0.3998(7) 0.57512(16) 0.5407(4) 0.0402(13) Uani 0.639(2) 1 d PU A 1 O7A O 0.5310(10) 0.4953(2) 0.3863(5) 0.0600(19) Uani 0.639(2) 1 d PU A 1 H7A H 0.5355 0.4875 0.3235 0.090 Uiso 0.639(2) 1 calc PR A 1 O8A O 0.8515(6) 0.49005(14) 0.6624(4) 0.0368(11) Uani 0.639(2) 1 d P A 1 O9A O 0.4976(6) 0.38984(13) 1.0690(3) 0.0393(11) Uani 0.639(2) 1 d P A 1 O10A O 0.2841(8) 0.3802(2) 0.9750(7) 0.0725(19) Uani 0.639(2) 1 d PU A 1 N3A N 0.5968(7) 0.51430(17) 0.6029(4) 0.0325(13) Uani 0.639(2) 1 d P A 1 H3A H 0.4880 0.5135 0.6098 0.039 Uiso 0.639(2) 1 calc PR A 1 N4A N 0.4156(7) 0.39518(15) 0.9867(4) 0.0332(12) Uani 0.639(2) 1 d P A 1 C24A C 0.5311(9) 0.5732(2) 0.4924(6) 0.0326(17) Uani 0.639(2) 1 d PU A 1 C25A C 0.6571(9) 0.5388(2) 0.5201(5) 0.0330(16) Uani 0.639(2) 1 d PU A 1 H25A H 0.7653 0.5514 0.5470 0.040 Uiso 0.639(2) 1 calc PR A 1 C26A C 0.6920(11) 0.5127(2) 0.4229(6) 0.046(2) Uani 0.639(2) 1 d PU A 1 H26C H 0.7375 0.5295 0.3668 0.055 Uiso 0.639(2) 1 calc PR A 1 H26D H 0.7739 0.4912 0.4427 0.055 Uiso 0.639(2) 1 calc PR A 1 C27A C 0.6922(8) 0.4933(2) 0.6679(6) 0.0255(15) Uani 0.639(2) 1 d PU A 1 C28A C 0.6149(8) 0.46882(17) 0.7527(5) 0.0320(14) Uani 0.639(2) 1 d P A 1 C29A C 0.7120(8) 0.45831(19) 0.8436(5) 0.0331(14) Uani 0.639(2) 1 d P A 1 H29A H 0.8256 0.4667 0.8511 0.040 Uiso 0.639(2) 1 calc PR A 1 C30A C 0.6459(8) 0.43566(17) 0.9240(5) 0.0304(14) Uani 0.639(2) 1 d P A 1 H30A H 0.7098 0.4291 0.9874 0.036 Uiso 0.639(2) 1 calc PR A 1 C31A C 0.4716(10) 0.4226(2) 0.9042(6) 0.0346(17) Uani 0.639(2) 1 d PU A 1 C32A C 0.3793(9) 0.4317(2) 0.8185(5) 0.0349(15) Uani 0.639(2) 1 d P A 1 H32A H 0.2688 0.4213 0.8080 0.042 Uiso 0.639(2) 1 calc PR A 1 C33A C 0.4450(9) 0.4569(2) 0.7417(5) 0.0371(16) Uani 0.639(2) 1 d PU A 1 H33A H 0.3754 0.4659 0.6829 0.045 Uiso 0.639(2) 1 calc PR A 1 O5B O 0.5553(14) 0.6058(3) 0.4356(7) 0.029(2) Uani 0.361(2) 1 d PU A 2 O6B O 0.3397(12) 0.5868(3) 0.5213(7) 0.037(2) Uani 0.361(2) 1 d PU A 2 O7B O 0.4703(17) 0.5010(4) 0.3769(9) 0.055(3) Uani 0.361(2) 1 d PU A 2 H7B H 0.5103 0.4889 0.3166 0.083 Uiso 0.36 1 d P A 2 O8B O 0.7505(12) 0.4930(3) 0.6668(8) 0.029(2) Uani 0.361(2) 1 d PU A 2 O9B O 0.3047(11) 0.3722(3) 0.9650(11) 0.056(3) Uani 0.361(2) 1 d PDU A 2 O10B O 0.0824(11) 0.3963(3) 0.9384(8) 0.064(3) Uani 0.361(2) 1 d PD A 2 N3B N 0.5011(15) 0.5207(3) 0.5955(7) 0.033(2) Uani 0.361(2) 1 d P A 2 H3B H 0.3918 0.5225 0.5993 0.040 Uiso 0.361(2) 1 calc PR A 2 N4B N 0.2184(9) 0.3966(3) 0.9453(9) 0.044(3) Uani 0.361(2) 1 d PD A 2 C24B C 0.4760(17) 0.5810(4) 0.4900(11) 0.027(3) Uani 0.361(2) 1 d PU A 2 C25B C 0.5832(16) 0.5434(4) 0.5157(10) 0.032(3) Uani 0.361(2) 1 d PU A 2 H25B H 0.6927 0.5530 0.5490 0.038 Uiso 0.361(2) 1 calc PR A 2 C26B C 0.6225(18) 0.5178(4) 0.4217(11) 0.035(3) Uani 0.361(2) 1 d PU A 2 H26E H 0.6757 0.5346 0.3686 0.043 Uiso 0.361(2) 1 calc PR A 2 H26F H 0.7013 0.4960 0.4443 0.043 Uiso 0.361(2) 1 calc PR A 2 C27B C 0.5933(17) 0.4965(3) 0.6656(9) 0.032(3) Uani 0.361(2) 1 d PU A 2 C28B C 0.4907(17) 0.4749(4) 0.7417(9) 0.035(3) Uani 0.361(2) 1 d PU A 2 C29B C 0.5743(18) 0.4587(4) 0.8326(9) 0.044(3) Uani 0.361(2) 1 d PU A 2 H29B H 0.6898 0.4652 0.8440 0.052 Uiso 0.361(2) 1 calc PR A 2 C30B C 0.5031(18) 0.4331(4) 0.9109(11) 0.033(3) Uani 0.361(2) 1 d PU A 2 H30B H 0.5610 0.4222 0.9721 0.040 Uiso 0.361(2) 1 calc PR A 2 C31B C 0.3191(17) 0.4271(4) 0.8775(11) 0.043(3) Uani 0.361(2) 1 d PU A 2 C32B C 0.2344(19) 0.4424(4) 0.7922(11) 0.049(3) Uani 0.361(2) 1 d PU A 2 H32B H 0.1186 0.4366 0.7795 0.059 Uiso 0.361(2) 1 calc PR A 2 C33B C 0.3148(17) 0.4666(4) 0.7228(10) 0.042(3) Uani 0.361(2) 1 d PU A 2 H33B H 0.2544 0.4778 0.6629 0.050 Uiso 0.361(2) 1 calc PR A 2 O1W O 0.5494(5) 0.47164(11) 0.1892(3) 0.0541(9) Uani 1 1 d . . . H11W H 0.4454 0.4691 0.1699 0.081 Uiso 1 1 d . . . H12W H 0.5987 0.4861 0.1428 0.081 Uiso 1 1 d . . . O2W O 0.7244(5) 0.52680(12) 0.0774(3) 0.0589(10) Uani 1 1 d . . . H21W H 0.8102 0.5110 0.0814 0.088 Uiso 1 1 d . . . H22W H 0.7577 0.5512 0.0908 0.088 Uiso 1 1 d . . . O3W O 0.8946(4) 0.60247(12) 0.3767(3) 0.0574(10) Uani 1 1 d . . . H31W H 0.9621 0.6181 0.4237 0.086 Uiso 1 1 d . . . H32W H 0.8019 0.6069 0.4065 0.086 Uiso 1 1 d . . . O4W O 0.1601(7) 0.63523(18) 0.4973(4) 0.0441(14) Uani 0.639(2) 1 d PU A 1 H41W H 0.1556 0.6602 0.5148 0.066 Uiso 0.64 1 d P A 1 H42W H 0.2096 0.6222 0.5486 0.066 Uiso 0.64 1 d P A 1 O5W O 0.8893(5) 0.59428(12) 0.1610(3) 0.0621(10) Uani 1 1 d . . . H51W H 0.9930 0.5905 0.1486 0.093 Uiso 1 1 d . . . H52W H 0.9131 0.5900 0.2270 0.093 Uiso 1 1 d . . . O6W O 0.1069(8) 0.52052(19) 0.5432(5) 0.0596(16) Uani 0.639(2) 1 d P A 1 H61W H 0.1543 0.5002 0.5097 0.089 Uiso 0.64 1 d P A 1 H62W H 0.0328 0.5101 0.5829 0.089 Uiso 0.64 1 d P A 1 O7W O 0.1781(12) 0.5335(2) 0.3159(5) 0.088(3) Uani 0.639(2) 1 d P A 1 H71W H 0.1109 0.5487 0.3484 0.133 Uiso 0.639(2) 1 d PR A 1 H72W H 0.2708 0.5285 0.3516 0.133 Uiso 0.639(2) 1 d PR A 1 O41W O 0.1023(12) 0.6466(3) 0.4980(8) 0.040(2) Uani 0.361(2) 1 d PU A 2 O61W O 0.2756(15) 0.5462(4) 0.3014(8) 0.062(3) Uani 0.361(2) 1 d P A 2 O71W O 0.0234(14) 0.5245(3) 0.4180(8) 0.062(3) Uani 0.361(2) 1 d P A 2 O81W O 0.1854(18) 0.5101(4) 0.6105(14) 0.097(5) Uani 0.361(2) 1 d P A 3 O91W O -0.0005(13) 0.4456(5) 0.7384(10) 0.090(4) Uani 0.361(2) 1 d P A 3 O10W O -0.0773(13) 0.4012(3) 0.9180(9) 0.065(3) Uani 0.361(2) 1 d P A 3 O5 O -0.0270(5) 0.47270(10) 0.0729(3) 0.0578(10) Uani 1 1 d . . . O6 O 0.2407(5) 0.45944(10) 0.1028(3) 0.0542(9) Uani 1 1 d . . . O7 O 0.2016(5) 0.56576(11) 0.1182(3) 0.0594(10) Uani 1 1 d . . . H7 H 0.2080 0.5544 0.1798 0.089 Uiso 1 1 d . . . O8 O 0.1779(5) 0.55553(13) -0.2029(3) 0.0716(12) Uani 1 1 d . . . O9 O -0.6371(5) 0.64784(12) -0.2989(3) 0.0672(11) Uani 1 1 d . . . O10 O -0.4660(7) 0.67342(12) -0.4071(3) 0.0807(14) Uani 1 1 d . . . N3 N 0.0259(5) 0.53245(10) -0.0705(3) 0.0404(9) Uani 1 1 d . . . H3 H -0.0731 0.5301 -0.0445 0.048 Uiso 1 1 calc R . . N4 N -0.5003(7) 0.65038(13) -0.3363(3) 0.0584(13) Uani 1 1 d . . . C24 C 0.1213(7) 0.47875(13) 0.0580(4) 0.0507(13) Uani 1 1 d . . . C25 C 0.1714(6) 0.51326(12) -0.0179(4) 0.0435(11) Uani 1 1 d . . . H25 H 0.2369 0.5007 -0.0739 0.052 Uiso 1 1 calc R . . C26 C 0.2839(6) 0.54424(14) 0.0388(5) 0.0555(14) Uani 1 1 d . . . H26A H 0.3836 0.5304 0.0719 0.067 Uiso 1 1 calc R . . H26B H 0.3230 0.5637 -0.0136 0.067 Uiso 1 1 calc R . . C27 C 0.0433(7) 0.55427(14) -0.1608(4) 0.0496(12) Uani 1 1 d . . . C28 C -0.1044(6) 0.57750(12) -0.2048(3) 0.0407(11) Uani 1 1 d . . . C29 C -0.0730(7) 0.60622(13) -0.2828(3) 0.0469(12) Uani 1 1 d . . . H29 H 0.0366 0.6090 -0.3067 0.056 Uiso 1 1 calc R . . C30 C -0.2020(8) 0.63043(14) -0.3248(3) 0.0547(14) Uani 1 1 d . . . H30 H -0.1804 0.6507 -0.3752 0.066 Uiso 1 1 calc R . . C31 C -0.3630(7) 0.62477(14) -0.2924(3) 0.0480(12) Uani 1 1 d . . . C32 C -0.4008(7) 0.59521(14) -0.2191(4) 0.0475(12) Uani 1 1 d . . . H32 H -0.5124 0.5910 -0.1999 0.057 Uiso 1 1 calc R . . C33 C -0.2667(6) 0.57194(13) -0.1748(3) 0.0420(11) Uani 1 1 d . . . H33 H -0.2878 0.5520 -0.1233 0.050 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0325(13) 0.0356(14) 0.0215(12) -0.0035(11) 0.0036(10) -0.0018(11) O2 0.0404(14) 0.0221(12) 0.0247(12) 0.0009(10) 0.0016(11) 0.0027(11) O3 0.0379(13) 0.0296(13) 0.0190(11) 0.0014(10) 0.0024(10) -0.0001(11) O4 0.0562(17) 0.0253(13) 0.0319(14) 0.0056(12) 0.0010(13) -0.0022(13) N1 0.0226(13) 0.0239(14) 0.0216(14) 0.0023(12) 0.0003(11) 0.0008(11) N2 0.067(2) 0.0213(15) 0.0314(17) 0.0002(14) 0.0046(16) 0.0033(16) C1 0.0256(16) 0.0214(16) 0.0255(16) -0.0013(14) 0.0014(13) 0.0004(14) C2 0.0225(16) 0.0233(17) 0.0291(17) -0.0026(15) -0.0014(13) 0.0018(14) C3 0.0239(15) 0.0263(17) 0.0188(15) 0.0025(14) 0.0004(12) 0.0041(14) C4 0.0304(17) 0.0263(17) 0.0228(16) 0.0066(14) -0.0028(14) 0.0004(15) C5 0.0242(16) 0.0238(17) 0.0226(16) 0.0002(14) 0.0015(13) -0.0003(14) C6 0.0221(15) 0.0264(17) 0.0222(16) -0.0016(14) -0.0019(13) -0.0020(14) C7 0.0322(18) 0.0242(17) 0.0220(16) -0.0003(14) 0.0012(14) 0.0030(15) C8 0.0262(17) 0.0231(17) 0.0231(16) -0.0001(14) 0.0020(14) 0.0010(14) C9 0.0290(18) 0.0282(18) 0.0282(18) 0.0015(15) 0.0041(15) 0.0034(15) C10 0.038(2) 0.035(2) 0.0231(17) 0.0042(16) 0.0003(15) 0.0003(17) C11 0.0292(18) 0.0319(19) 0.0281(18) 0.0008(16) 0.0014(15) 0.0046(16) C12 0.046(2) 0.048(2) 0.031(2) -0.0095(19) -0.0024(18) -0.010(2) C13 0.045(2) 0.034(2) 0.041(2) -0.0097(18) 0.0027(19) -0.0049(19) C14 0.043(2) 0.031(2) 0.035(2) -0.0060(17) -0.0005(18) -0.0099(18) C15 0.072(3) 0.028(2) 0.041(2) -0.0100(18) 0.014(2) -0.011(2) C16 0.054(2) 0.0243(18) 0.031(2) 0.0022(16) 0.0000(18) 0.0137(18) C17 0.040(2) 0.0292(19) 0.0289(18) 0.0016(16) 0.0031(16) 0.0107(17) C18 0.0263(17) 0.0302(18) 0.0213(16) -0.0001(15) 0.0035(13) 0.0030(15) C19 0.0319(19) 0.044(2) 0.0303(19) -0.0043(18) 0.0053(15) -0.0127(18) C20 0.039(2) 0.038(2) 0.041(2) -0.0048(19) 0.0125(18) -0.0130(18) C21 0.044(2) 0.0211(17) 0.0292(18) -0.0054(15) 0.0109(16) -0.0031(16) C22 0.058(3) 0.0226(18) 0.034(2) 0.0026(16) 0.0023(19) -0.0028(18) C23 0.0386(19) 0.0292(19) 0.0251(17) 0.0082(15) 0.0007(15) 0.0000(16) O1A 0.0371(14) 0.0525(17) 0.0200(12) -0.0077(12) 0.0009(11) 0.0012(13) O2A 0.0303(12) 0.0296(13) 0.0255(12) 0.0078(11) 0.0047(10) 0.0064(11) O3A 0.0325(12) 0.0311(13) 0.0201(11) 0.0033(10) 0.0053(10) 0.0031(11) O4A 0.0587(18) 0.0412(17) 0.0290(14) 0.0052(13) 0.0100(13) -0.0005(14) N1A 0.0292(15) 0.0380(17) 0.0184(14) 0.0022(13) 0.0019(12) -0.0024(13) N2A 0.0393(17) 0.0376(18) 0.0267(15) -0.0055(14) 0.0018(14) -0.0055(15) C1A 0.0267(17) 0.0331(19) 0.0234(17) 0.0046(15) 0.0045(14) 0.0001(16) C2A 0.0223(16) 0.0281(18) 0.0285(17) 0.0032(15) 0.0074(14) 0.0038(14) C3A 0.0272(17) 0.0348(19) 0.0169(15) 0.0022(15) 0.0048(13) -0.0002(15) C4A 0.0265(17) 0.0281(18) 0.0228(16) 0.0024(14) 0.0042(13) 0.0006(15) C5A 0.0249(17) 0.036(2) 0.0217(16) -0.0030(15) 0.0006(13) -0.0025(15) C6A 0.0227(16) 0.040(2) 0.0188(16) 0.0020(15) 0.0050(13) -0.0022(15) C7A 0.0297(17) 0.036(2) 0.0169(15) -0.0011(15) 0.0005(13) -0.0015(16) C8A 0.0255(17) 0.0332(19) 0.0239(17) -0.0020(15) 0.0011(14) -0.0019(15) C9A 0.0319(18) 0.037(2) 0.0282(18) 0.0054(16) 0.0047(15) -0.0042(16) C10A 0.0338(19) 0.047(2) 0.0206(16) 0.0031(17) 0.0003(15) -0.0104(18) C11A 0.0270(18) 0.058(3) 0.0184(16) 0.0035(17) 0.0012(14) -0.0036(18) C12A 0.052(2) 0.063(3) 0.0235(19) -0.010(2) 0.0013(18) 0.014(2) C13A 0.037(2) 0.045(2) 0.0310(19) -0.0110(18) -0.0003(16) 0.0079(19) C14A 0.0339(19) 0.043(2) 0.0284(18) -0.0050(17) 0.0052(16) 0.0071(18) C15A 0.040(2) 0.042(2) 0.0253(19) -0.0094(17) 0.0024(16) 0.0018(18) C16A 0.037(2) 0.043(2) 0.0291(19) -0.0046(18) 0.0053(16) -0.0076(18) C17A 0.0321(18) 0.041(2) 0.0217(17) 0.0007(16) 0.0042(14) -0.0069(17) C18A 0.0298(18) 0.044(2) 0.0192(16) 0.0007(16) 0.0023(14) -0.0028(17) C19A 0.0290(18) 0.049(2) 0.0226(17) -0.0043(17) 0.0016(14) -0.0010(18) C20A 0.0322(19) 0.044(2) 0.0258(18) -0.0028(17) -0.0032(15) 0.0037(18) C21A 0.0362(19) 0.039(2) 0.0170(16) -0.0043(15) -0.0029(14) 0.0000(17) C22A 0.043(2) 0.033(2) 0.0296(19) 0.0074(16) 0.0074(17) -0.0049(17) C23A 0.0382(19) 0.034(2) 0.0199(16) 0.0056(15) 0.0035(15) 0.0058(17) O5A 0.066(3) 0.033(3) 0.020(2) -0.007(2) 0.009(2) -0.011(2) O6A 0.056(3) 0.040(3) 0.025(2) -0.001(2) 0.003(2) -0.003(2) O7A 0.101(5) 0.052(3) 0.026(3) -0.008(2) -0.003(3) -0.022(3) O8A 0.038(2) 0.033(2) 0.040(2) 0.0084(19) 0.006(2) -0.003(2) O9A 0.061(3) 0.032(2) 0.027(2) 0.0065(18) 0.017(2) 0.002(2) O10A 0.065(3) 0.049(3) 0.109(4) -0.018(3) 0.055(3) 0.000(3) N3A 0.040(3) 0.036(3) 0.021(2) -0.002(2) 0.005(2) -0.004(3) N4A 0.048(3) 0.021(2) 0.032(3) -0.007(2) 0.006(2) -0.011(2) C24A 0.042(4) 0.028(3) 0.028(3) -0.011(3) 0.004(3) -0.007(3) C25A 0.045(4) 0.028(3) 0.025(3) 0.001(2) -0.003(3) -0.001(3) C26A 0.070(5) 0.037(4) 0.031(3) -0.003(3) 0.013(3) -0.011(4) C27A 0.016(3) 0.028(3) 0.033(3) 0.001(2) 0.005(3) 0.007(3) C28A 0.050(4) 0.015(3) 0.031(3) -0.009(2) 0.012(3) -0.014(3) C29A 0.041(3) 0.029(3) 0.030(3) 0.005(2) 0.008(3) -0.004(3) C30A 0.048(4) 0.023(3) 0.021(3) 0.002(2) 0.005(2) -0.001(3) C31A 0.046(4) 0.029(3) 0.030(3) -0.017(3) 0.010(3) -0.019(3) C32A 0.045(3) 0.040(3) 0.020(3) -0.002(3) 0.005(3) -0.015(3) C33A 0.050(4) 0.043(4) 0.019(3) -0.005(3) 0.004(3) -0.009(3) O5B 0.046(4) 0.029(4) 0.015(3) -0.013(3) 0.009(3) -0.011(3) O6B 0.047(5) 0.034(4) 0.030(4) 0.000(3) -0.001(4) 0.001(4) O7B 0.090(7) 0.045(5) 0.031(4) -0.014(4) 0.007(5) -0.035(5) O8B 0.022(5) 0.025(4) 0.039(4) 0.000(3) -0.011(4) 0.010(4) O9B 0.058(4) 0.050(4) 0.063(4) -0.008(3) 0.018(3) 0.001(3) O10B 0.087(7) 0.054(6) 0.056(6) 0.006(5) 0.033(5) 0.010(6) N3B 0.056(6) 0.025(5) 0.019(4) 0.003(4) 0.005(4) -0.003(5) N4B 0.047(6) 0.037(6) 0.048(6) -0.014(5) 0.007(5) 0.023(5) C24B 0.031(5) 0.024(4) 0.026(4) -0.009(4) 0.001(4) 0.001(4) C25B 0.037(5) 0.028(4) 0.030(4) 0.003(4) 0.003(4) 0.005(4) C26B 0.047(6) 0.027(4) 0.034(4) 0.005(4) 0.013(4) -0.008(4) C27B 0.047(6) 0.022(5) 0.026(5) 0.005(4) 0.000(5) -0.004(5) C28B 0.042(5) 0.034(5) 0.028(4) -0.002(4) 0.004(4) -0.006(4) C29B 0.057(6) 0.043(5) 0.030(5) 0.019(4) 0.002(5) 0.002(5) C30B 0.039(5) 0.034(5) 0.026(4) -0.003(4) 0.010(4) -0.007(4) C31B 0.053(6) 0.034(5) 0.043(6) -0.005(5) 0.013(5) 0.013(5) C32B 0.060(6) 0.045(6) 0.043(6) -0.002(5) 0.001(5) -0.011(5) C33B 0.049(6) 0.042(5) 0.035(5) -0.005(5) 0.006(5) -0.005(5) O1W 0.064(2) 0.056(2) 0.0407(17) -0.0028(16) -0.0054(15) 0.0078(17) O2W 0.061(2) 0.062(2) 0.054(2) 0.0085(18) 0.0066(17) 0.0052(18) O3W 0.061(2) 0.065(2) 0.0446(18) -0.0102(17) -0.0061(16) -0.0095(18) O4W 0.045(3) 0.059(3) 0.027(2) -0.003(2) -0.004(2) -0.003(3) O5W 0.060(2) 0.070(2) 0.055(2) -0.0065(19) -0.0017(17) 0.0045(19) O6W 0.067(3) 0.063(3) 0.052(3) -0.004(3) 0.025(3) -0.015(3) O7W 0.149(7) 0.070(4) 0.047(4) -0.017(3) 0.013(4) -0.021(5) O41W 0.036(5) 0.047(5) 0.035(4) -0.009(4) -0.001(4) 0.011(4) O61W 0.075(7) 0.071(7) 0.037(5) 0.005(5) -0.016(5) -0.018(6) O71W 0.081(7) 0.049(6) 0.056(6) -0.010(5) 0.018(5) 0.009(5) O81W 0.082(9) 0.069(8) 0.139(13) -0.032(9) 0.008(9) 0.013(7) O91W 0.045(6) 0.152(12) 0.076(8) -0.031(8) 0.005(5) 0.033(7) O10W 0.059(6) 0.069(6) 0.063(6) -0.013(5) -0.027(5) 0.013(5) O5 0.063(2) 0.0406(18) 0.072(2) 0.0221(17) 0.0191(18) -0.0041(16) O6 0.080(2) 0.0298(16) 0.0508(19) 0.0073(14) -0.0118(18) 0.0029(16) O7 0.061(2) 0.0410(19) 0.076(2) 0.0040(18) 0.0002(19) -0.0044(17) O8 0.073(2) 0.072(2) 0.072(2) 0.033(2) 0.025(2) 0.001(2) O9 0.088(3) 0.062(2) 0.048(2) -0.0119(18) -0.0271(19) 0.019(2) O10 0.150(4) 0.055(2) 0.0357(19) 0.0021(17) -0.006(2) 0.023(3) N3 0.056(2) 0.0269(17) 0.0387(19) 0.0118(15) 0.0089(16) -0.0022(16) N4 0.111(4) 0.042(2) 0.0190(17) -0.0114(16) -0.021(2) 0.003(2) C24 0.073(3) 0.021(2) 0.060(3) 0.001(2) 0.016(3) -0.009(2) C25 0.051(2) 0.0211(19) 0.059(3) 0.0118(19) 0.011(2) 0.0044(18) C26 0.048(3) 0.023(2) 0.096(4) 0.013(2) 0.009(3) 0.0007(19) C27 0.073(3) 0.033(2) 0.045(2) 0.014(2) 0.017(2) -0.006(2) C28 0.068(3) 0.0255(19) 0.029(2) -0.0004(17) 0.0042(19) -0.007(2) C29 0.079(3) 0.032(2) 0.029(2) 0.0001(18) 0.002(2) -0.011(2) C30 0.108(4) 0.028(2) 0.026(2) -0.0009(18) -0.009(2) -0.006(3) C31 0.083(3) 0.035(2) 0.0241(19) -0.0112(18) -0.009(2) 0.012(2) C32 0.069(3) 0.037(2) 0.035(2) -0.0118(19) -0.008(2) 0.006(2) C33 0.068(3) 0.027(2) 0.031(2) -0.0029(17) 0.002(2) 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 1.431(5) . ? O1 C12 1.434(5) . ? O2 C2 1.366(4) . ? O2 C22 1.439(5) . ? O3 C3 1.367(4) . ? O3 C23 1.445(4) . ? O4 C9 1.239(5) . ? N1 C9 1.363(5) . ? N1 C6 1.420(4) . ? N1 C8 1.492(4) . ? N2 C16 1.517(6) . ? N2 C15 1.519(6) . ? N2 C21 1.542(5) . ? N2 H2 0.9300 . ? C1 C2 1.395(5) . ? C1 C6 1.411(5) . ? C1 H1 0.9500 . ? C2 C3 1.419(5) . ? C3 C4 1.385(5) . ? C4 C5 1.393(5) . ? C4 H4 0.9500 . ? C5 C6 1.386(5) . ? C5 C7 1.503(5) . ? C7 C21 1.544(5) . ? C7 C8 1.546(5) . ? C7 C17 1.557(5) . ? C8 C18 1.528(5) . ? C8 H8 1.0000 . ? C9 C10 1.506(5) . ? C10 C11 1.550(6) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C18 1.541(5) . ? C11 H11 1.0000 . ? C12 C13 1.510(6) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.320(6) . ? C13 H13 0.9500 . ? C14 C19 1.523(6) . ? C14 C15 1.529(6) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 C17 1.498(6) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 C19 1.532(6) . ? C18 H18 1.0000 . ? C19 C20 1.562(6) . ? C19 H19 1.0000 . ? C20 C21 1.500(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 . ? O1A C11A 1.431(5) . ? O1A C12A 1.443(5) . ? O2A C2A 1.375(4) . ? O2A C22A 1.442(5) . ? O3A C3A 1.354(4) . ? O3A C23A 1.449(4) . ? O4A C9A 1.233(5) . ? N1A C9A 1.362(5) . ? N1A C6A 1.419(4) . ? N1A C8A 1.495(5) . ? N2A C15A 1.514(5) . ? N2A C16A 1.522(5) . ? N2A C21A 1.537(5) . ? N2A H2A 0.9300 . ? C1A C6A 1.398(5) . ? C1A C2A 1.402(5) . ? C1A H1A 0.9500 . ? C2A C3A 1.415(5) . ? C3A C4A 1.400(5) . ? C4A C5A 1.405(5) . ? C4A H4A 0.9500 . ? C5A C6A 1.377(5) . ? C5A C7A 1.510(5) . ? C7A C17A 1.538(5) . ? C7A C21A 1.547(5) . ? C7A C8A 1.552(5) . ? C8A C18A 1.534(5) . ? C8A H8A 1.0000 . ? C9A C10A 1.520(6) . ? C10A C11A 1.531(6) . ? C10A H10C 0.9900 . ? C10A H10D 0.9900 . ? C11A C18A 1.541(5) . ? C11A H11A 1.0000 . ? C12A C13A 1.496(7) . ? C12A H12C 0.9900 . ? C12A H12D 0.9900 . ? C13A C14A 1.339(6) . ? C13A H13A 0.9500 . ? C14A C15A 1.476(6) . ? C14A C19A 1.537(6) . ? C15A H15C 0.9900 . ? C15A H15D 0.9900 . ? C16A C17A 1.530(6) . ? C16A H16C 0.9900 . ? C16A H16D 0.9900 . ? C17A H17C 0.9900 . ? C17A H17D 0.9900 . ? C18A C19A 1.522(6) . ? C18A H18A 1.0000 . ? C19A C20A 1.531(5) . ? C19A H19A 1.0000 . ? C20A C21A 1.513(6) . ? C20A H20C 0.9900 . ? C20A H20D 0.9900 . ? C21A H21A 1.0000 . ? C22A H22D 0.9800 . ? C22A H22E 0.9800 . ? C22A H22F 0.9800 . ? C23A H23D 0.9800 . ? C23A H23E 0.9800 . ? C23A H23F 0.9800 . ? O5A C24A 1.302(9) . ? O6A C24A 1.250(9) . ? O7A C26A 1.460(11) . ? O7A H7A 0.8400 . ? O7A H7B 0.9141 . ? O8A C27A 1.285(8) . ? O9A N4A 1.210(7) . ? O10A N4A 1.164(8) . ? N3A C27A 1.290(9) . ? N3A C25A 1.435(9) . ? N3A H3A 0.8800 . ? N4A C31A 1.477(9) . ? C24A C25A 1.547(10) . ? C25A C26A 1.546(10) . ? C25A H25A 1.0000 . ? C26A H26C 0.9900 . ? C26A H26D 0.9900 . ? C27A C28A 1.510(9) . ? C28A C29A 1.393(9) . ? C28A C33A 1.413(10) . ? C29A C30A 1.396(8) . ? C29A H29A 0.9500 . ? C30A C31A 1.466(10) . ? C30A H30A 0.9500 . ? C31A C32A 1.309(10) . ? C32A C33A 1.410(9) . ? C32A H32A 0.9500 . ? C33A H33A 0.9500 . ? O5B C24B 1.269(18) . ? O6B C24B 1.198(17) . ? O7B C26B 1.424(19) . ? O7B H7B 0.9378 . ? O8B C27B 1.261(16) . ? O9B N4B 1.082(9) . ? O10B N4B 1.085(9) . ? N3B C27B 1.377(15) . ? N3B C25B 1.450(16) . ? N3B H3B 0.8800 . ? N4B C31B 1.579(18) . ? C24B C25B 1.536(17) . ? C25B C26B 1.511(19) . ? C25B H25B 1.0000 . ? C26B H26E 0.9900 . ? C26B H26F 0.9900 . ? C27B C28B 1.489(18) . ? C28B C29B 1.402(17) . ? C28B C33B 1.437(19) . ? C29B C30B 1.448(19) . ? C29B H29B 0.9500 . ? C30B C31B 1.52(2) . ? C30B H30B 0.9500 . ? C31B C32B 1.340(19) . ? C32B C33B 1.379(19) . ? C32B H32B 0.9500 . ? C33B H33B 0.9500 . ? O1W H11W 0.8559 . ? O1W H12W 0.8726 . ? O2W H21W 0.8624 . ? O2W H22W 0.8654 . ? O3W H31W 0.9343 . ? O3W H32W 0.8657 . ? O4W H41W 0.8566 . ? O4W H42W 0.8574 . ? O5W H51W 0.8630 . ? O5W H52W 0.8580 . ? O6W H61W 0.8938 . ? O6W H62W 0.8725 . ? O7W H71W 0.8598 . ? O7W H72W 0.8599 . ? O41W H41W 0.6447 . ? O41W H42W 1.3171 . ? O61W H72W 0.8684 . ? O71W H71W 1.4099 . ? O81W H61W 1.3278 . ? O81W H62W 1.2488 . ? O5 C24 1.229(6) . ? O6 C24 1.256(6) . ? O7 C26 1.428(7) . ? O7 H7 0.8652 . ? O8 C27 1.232(6) . ? O9 N4 1.222(6) . ? O10 N4 1.223(6) . ? N3 C27 1.369(6) . ? N3 C25 1.451(6) . ? N3 H3 0.8800 . ? N4 C31 1.469(7) . ? C24 C25 1.562(6) . ? C25 C26 1.516(7) . ? C25 H25 1.0000 . ? C26 H26A 0.9900 . ? C26 H26B 0.9900 . ? C27 C28 1.489(7) . ? C28 C33 1.387(7) . ? C28 C29 1.406(6) . ? C29 C30 1.387(7) . ? C29 H29 0.9500 . ? C30 C31 1.388(8) . ? C30 H30 0.9500 . ? C31 C32 1.396(7) . ? C32 C33 1.409(7) . ? C32 H32 0.9500 . ? C33 H33 0.9500 . ? 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 115.7(3) . . ? C2 O2 C22 116.8(3) . . ? C3 O3 C23 116.1(3) . . ? C9 N1 C6 125.8(3) . . ? C9 N1 C8 120.4(3) . . ? C6 N1 C8 108.6(3) . . ? C16 N2 C15 112.0(3) . . ? C16 N2 C21 107.2(3) . . ? C15 N2 C21 112.7(3) . . ? C16 N2 H2 108.3 . . ? C15 N2 H2 108.3 . . ? C21 N2 H2 108.3 . . ? C2 C1 C6 117.6(3) . . ? C2 C1 H1 121.2 . . ? C6 C1 H1 121.2 . . ? O2 C2 C1 123.7(3) . . ? O2 C2 C3 115.6(3) . . ? C1 C2 C3 120.7(3) . . ? O3 C3 C4 125.3(3) . . ? O3 C3 C2 114.8(3) . . ? C4 C3 C2 119.9(3) . . ? C3 C4 C5 120.1(3) . . ? C3 C4 H4 119.9 . . ? C5 C4 H4 119.9 . . ? C6 C5 C4 119.7(3) . . ? C6 C5 C7 110.9(3) . . ? C4 C5 C7 129.3(3) . . ? C5 C6 C1 121.9(3) . . ? C5 C6 N1 110.0(3) . . ? C1 C6 N1 128.0(3) . . ? C5 C7 C21 116.1(3) . . ? C5 C7 C8 102.4(3) . . ? C21 C7 C8 114.4(3) . . ? C5 C7 C17 111.6(3) . . ? C21 C7 C17 101.1(3) . . ? C8 C7 C17 111.6(3) . . ? N1 C8 C18 106.1(3) . . ? N1 C8 C7 105.2(3) . . ? C18 C8 C7 117.2(3) . . ? N1 C8 H8 109.3 . . ? C18 C8 H8 109.3 . . ? C7 C8 H8 109.3 . . ? O4 C9 N1 122.0(3) . . ? O4 C9 C10 121.4(3) . . ? N1 C9 C10 116.6(3) . . ? C9 C10 C11 118.3(3) . . ? 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 113.3(3) . . ? O1 C11 C10 105.4(3) . . ? C18 C11 C10 110.6(3) . . ? O1 C11 H11 109.1 . . ? C18 C11 H11 109.1 . . ? C10 C11 H11 109.1 . . ? O1 C12 C13 112.0(3) . . ? O1 C12 H12A 109.2 . . ? C13 C12 H12A 109.2 . . ? O1 C12 H12B 109.2 . . ? C13 C12 H12B 109.2 . . ? H12A C12 H12B 107.9 . . ? C14 C13 C12 122.6(4) . . ? C14 C13 H13 118.7 . . ? C12 C13 H13 118.7 . . ? C13 C14 C19 123.2(4) . . ? C13 C14 C15 121.5(4) . . ? C19 C14 C15 115.2(4) . . ? N2 C15 C14 109.9(3) . . ? 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 104.5(3) . . ? C17 C16 H16A 110.8 . . ? N2 C16 H16A 110.8 . . ? C17 C16 H16B 110.8 . . ? N2 C16 H16B 110.8 . . ? H16A C16 H16B 108.9 . . ? C16 C17 C7 103.9(3) . . ? C16 C17 H17A 111.0 . . ? C7 C17 H17A 111.0 . . ? C16 C17 H17B 111.0 . . ? C7 C17 H17B 111.0 . . ? H17A C17 H17B 109.0 . . ? C8 C18 C19 112.7(3) . . ? C8 C18 C11 107.3(3) . . ? C19 C18 C11 117.8(3) . . ? C8 C18 H18 106.1 . . ? C19 C18 H18 106.1 . . ? C11 C18 H18 106.1 . . ? C14 C19 C18 115.3(3) . . ? C14 C19 C20 108.8(3) . . ? C18 C19 C20 105.4(3) . . ? C14 C19 H19 109.0 . . ? C18 C19 H19 109.0 . . ? C20 C19 H19 109.0 . . ? C21 C20 C19 108.7(3) . . ? 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 N2 111.1(3) . . ? C20 C21 C7 115.6(3) . . ? N2 C21 C7 105.2(3) . . ? C20 C21 H21 108.2 . . ? N2 C21 H21 108.2 . . ? C7 C21 H21 108.2 . . ? 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 . . ? C11A O1A C12A 114.4(3) . . ? C2A O2A C22A 116.4(3) . . ? C3A O3A C23A 116.8(3) . . ? C9A N1A C6A 126.0(3) . . ? C9A N1A C8A 119.6(3) . . ? C6A N1A C8A 109.4(3) . . ? C15A N2A C16A 112.3(3) . . ? C15A N2A C21A 112.9(3) . . ? C16A N2A C21A 107.7(3) . . ? C15A N2A H2A 107.9 . . ? C16A N2A H2A 107.9 . . ? C21A N2A H2A 107.9 . . ? C6A C1A C2A 117.2(3) . . ? C6A C1A H1A 121.4 . . ? C2A C1A H1A 121.4 . . ? O2A C2A C1A 123.2(3) . . ? O2A C2A C3A 115.0(3) . . ? C1A C2A C3A 121.8(3) . . ? O3A C3A C4A 125.0(3) . . ? O3A C3A C2A 116.1(3) . . ? C4A C3A C2A 118.9(3) . . ? C3A C4A C5A 119.4(3) . . ? C3A C4A H4A 120.3 . . ? C5A C4A H4A 120.3 . . ? C6A C5A C4A 120.3(3) . . ? C6A C5A C7A 111.0(3) . . ? C4A C5A C7A 128.6(3) . . ? C5A C6A C1A 122.3(3) . . ? C5A C6A N1A 109.9(3) . . ? C1A C6A N1A 127.8(3) . . ? C5A C7A C17A 111.2(3) . . ? C5A C7A C21A 115.3(3) . . ? C17A C7A C21A 102.3(3) . . ? C5A C7A C8A 102.6(3) . . ? C17A C7A C8A 111.6(3) . . ? C21A C7A C8A 114.2(3) . . ? N1A C8A C18A 105.9(3) . . ? N1A C8A C7A 104.3(3) . . ? C18A C8A C7A 117.2(3) . . ? N1A C8A H8A 109.7 . . ? C18A C8A H8A 109.7 . . ? C7A C8A H8A 109.7 . . ? O4A C9A N1A 121.1(4) . . ? O4A C9A C10A 122.4(4) . . ? N1A C9A C10A 116.5(4) . . ? C9A C10A C11A 118.0(3) . . ? C9A C10A H10C 107.8 . . ? C11A C10A H10C 107.8 . . ? C9A C10A H10D 107.8 . . ? C11A C10A H10D 107.8 . . ? H10C C10A H10D 107.1 . . ? O1A C11A C10A 104.5(3) . . ? O1A C11A C18A 113.8(3) . . ? C10A C11A C18A 111.0(3) . . ? O1A C11A H11A 109.1 . . ? C10A C11A H11A 109.1 . . ? C18A C11A H11A 109.1 . . ? O1A C12A C13A 111.9(3) . . ? O1A C12A H12C 109.2 . . ? C13A C12A H12C 109.2 . . ? O1A C12A H12D 109.2 . . ? C13A C12A H12D 109.2 . . ? H12C C12A H12D 107.9 . . ? C14A C13A C12A 122.5(4) . . ? C14A C13A H13A 118.7 . . ? C12A C13A H13A 118.7 . . ? C13A C14A C15A 122.1(4) . . ? C13A C14A C19A 122.3(4) . . ? C15A C14A C19A 115.6(3) . . ? C14A C15A N2A 110.8(3) . . ? C14A C15A H15C 109.5 . . ? N2A C15A H15C 109.5 . . ? C14A C15A H15D 109.5 . . ? N2A C15A H15D 109.5 . . ? H15C C15A H15D 108.1 . . ? N2A C16A C17A 104.7(3) . . ? N2A C16A H16C 110.8 . . ? C17A C16A H16C 110.8 . . ? N2A C16A H16D 110.8 . . ? C17A C16A H16D 110.8 . . ? H16C C16A H16D 108.9 . . ? C16A C17A C7A 104.0(3) . . ? C16A C17A H17C 110.9 . . ? C7A C17A H17C 110.9 . . ? C16A C17A H17D 110.9 . . ? C7A C17A H17D 110.9 . . ? H17C C17A H17D 109.0 . . ? C19A C18A C8A 112.4(3) . . ? C19A C18A C11A 119.1(3) . . ? C8A C18A C11A 106.9(3) . . ? C19A C18A H18A 105.8 . . ? C8A C18A H18A 105.8 . . ? C11A C18A H18A 105.8 . . ? C18A C19A C20A 106.8(3) . . ? C18A C19A C14A 114.5(3) . . ? C20A C19A C14A 108.7(3) . . ? C18A C19A H19A 108.9 . . ? C20A C19A H19A 108.9 . . ? C14A C19A H19A 108.9 . . ? C21A C20A C19A 108.8(3) . . ? C21A C20A H20C 109.9 . . ? C19A C20A H20C 109.9 . . ? C21A C20A H20D 109.9 . . ? C19A C20A H20D 109.9 . . ? H20C C20A H20D 108.3 . . ? C20A C21A N2A 110.3(3) . . ? C20A C21A C7A 115.6(3) . . ? N2A C21A C7A 105.0(3) . . ? C20A C21A H21A 108.5 . . ? N2A C21A H21A 108.5 . . ? C7A C21A H21A 108.5 . . ? O2A C22A H22D 109.5 . . ? O2A C22A H22E 109.5 . . ? H22D C22A H22E 109.5 . . ? O2A C22A H22F 109.5 . . ? H22D C22A H22F 109.5 . . ? H22E C22A H22F 109.5 . . ? O3A C23A H23D 109.5 . . ? O3A C23A H23E 109.5 . . ? H23D C23A H23E 109.5 . . ? O3A C23A H23F 109.5 . . ? H23D C23A H23F 109.5 . . ? H23E C23A H23F 109.5 . . ? C26A O7A H7A 109.5 . . ? C26A O7A H7B 120.1 . . ? H7A O7A H7B 13.5 . . ? C27A N3A C25A 124.1(6) . . ? C27A N3A H3A 118.0 . . ? C25A N3A H3A 118.0 . . ? O10A N4A O9A 118.9(6) . . ? O10A N4A C31A 119.0(7) . . ? O9A N4A C31A 122.0(5) . . ? O6A C24A O5A 125.2(7) . . ? O6A C24A C25A 118.7(6) . . ? O5A C24A C25A 116.1(6) . . ? N3A C25A C26A 110.6(6) . . ? N3A C25A C24A 109.9(6) . . ? C26A C25A C24A 112.3(6) . . ? N3A C25A H25A 108.0 . . ? C26A C25A H25A 108.0 . . ? C24A C25A H25A 108.0 . . ? O7A C26A C25A 106.0(7) . . ? O7A C26A H26C 110.5 . . ? C25A C26A H26C 110.5 . . ? O7A C26A H26D 110.5 . . ? C25A C26A H26D 110.5 . . ? H26C C26A H26D 108.7 . . ? O8A C27A N3A 124.0(7) . . ? O8A C27A C28A 116.4(6) . . ? N3A C27A C28A 119.5(6) . . ? C29A C28A C33A 119.7(6) . . ? C29A C28A C27A 119.5(6) . . ? C33A C28A C27A 120.9(6) . . ? C28A C29A C30A 121.5(6) . . ? C28A C29A H29A 119.3 . . ? C30A C29A H29A 119.3 . . ? C29A C30A C31A 115.6(6) . . ? C29A C30A H30A 122.2 . . ? C31A C30A H30A 122.2 . . ? C32A C31A C30A 123.7(7) . . ? C32A C31A N4A 123.3(6) . . ? C30A C31A N4A 112.8(6) . . ? C31A C32A C33A 119.6(7) . . ? C31A C32A H32A 120.2 . . ? C33A C32A H32A 120.2 . . ? C32A C33A C28A 119.6(6) . . ? C32A C33A H33A 120.2 . . ? C28A C33A H33A 120.2 . . ? C26B O7B H7B 99.6 . . ? C27B N3B C25B 120.3(11) . . ? C27B N3B H3B 119.8 . . ? C25B N3B H3B 119.8 . . ? O9B N4B O10B 129.3(13) . . ? O9B N4B C31B 105.3(10) . . ? O10B N4B C31B 120.2(10) . . ? O6B C24B O5B 124.8(12) . . ? O6B C24B C25B 124.6(13) . . ? O5B C24B C25B 110.5(12) . . ? N3B C25B C26B 112.7(11) . . ? N3B C25B C24B 107.3(11) . . ? C26B C25B C24B 115.4(11) . . ? N3B C25B H25B 107.0 . . ? C26B C25B H25B 107.0 . . ? C24B C25B H25B 107.0 . . ? O7B C26B C25B 108.6(11) . . ? O7B C26B H26E 110.0 . . ? C25B C26B H26E 110.0 . . ? O7B C26B H26F 110.0 . . ? C25B C26B H26F 110.0 . . ? H26E C26B H26F 108.4 . . ? O8B C27B N3B 123.6(11) . . ? O8B C27B C28B 122.5(11) . . ? N3B C27B C28B 113.8(12) . . ? C29B C28B C33B 118.4(12) . . ? C29B C28B C27B 117.6(12) . . ? C33B C28B C27B 123.8(11) . . ? C28B C29B C30B 126.8(13) . . ? C28B C29B H29B 116.6 . . ? C30B C29B H29B 116.6 . . ? C29B C30B C31B 107.6(12) . . ? C29B C30B H30B 126.2 . . ? C31B C30B H30B 126.2 . . ? C32B C31B C30B 127.3(13) . . ? C32B C31B N4B 115.7(12) . . ? C30B C31B N4B 116.8(10) . . ? C31B C32B C33B 120.3(14) . . ? C31B C32B H32B 119.9 . . ? C33B C32B H32B 119.9 . . ? C32B C33B C28B 119.6(12) . . ? C32B C33B H33B 120.2 . . ? C28B C33B H33B 120.2 . . ? H11W O1W H12W 109.4 . . ? H21W O2W H22W 108.9 . . ? H31W O3W H32W 95.9 . . ? H41W O4W H42W 108.3 . . ? H51W O5W H52W 89.9 . . ? H61W O6W H62W 107.4 . . ? H71W O7W H72W 113.8 . . ? H41W O41W H42W 82.5 . . ? H61W O81W H62W 67.0 . . ? C26 O7 H7 114.6 . . ? C27 N3 C25 119.7(4) . . ? C27 N3 H3 120.1 . . ? C25 N3 H3 120.1 . . ? O9 N4 O10 125.1(5) . . ? O9 N4 C31 118.6(4) . . ? O10 N4 C31 116.2(5) . . ? O5 C24 O6 124.1(4) . . ? O5 C24 C25 120.1(4) . . ? O6 C24 C25 115.8(4) . . ? N3 C25 C26 110.9(4) . . ? N3 C25 C24 112.0(4) . . ? C26 C25 C24 111.8(4) . . ? N3 C25 H25 107.3 . . ? C26 C25 H25 107.3 . . ? C24 C25 H25 107.3 . . ? O7 C26 C25 112.7(4) . . ? O7 C26 H26A 109.0 . . ? C25 C26 H26A 109.0 . . ? O7 C26 H26B 109.0 . . ? C25 C26 H26B 109.0 . . ? H26A C26 H26B 107.8 . . ? O8 C27 N3 121.2(5) . . ? O8 C27 C28 121.0(4) . . ? N3 C27 C28 117.8(4) . . ? C33 C28 C29 119.6(4) . . ? C33 C28 C27 124.2(4) . . ? C29 C28 C27 116.2(4) . . ? C30 C29 C28 120.0(5) . . ? C30 C29 H29 120.0 . . ? C28 C29 H29 120.0 . . ? C29 C30 C31 119.3(4) . . ? C29 C30 H30 120.3 . . ? C31 C30 H30 120.3 . . ? C30 C31 C32 122.3(5) . . ? C30 C31 N4 119.7(4) . . ? C32 C31 N4 118.0(5) . . ? C31 C32 C33 117.3(5) . . ? C31 C32 H32 121.3 . . ? C33 C32 H32 121.3 . . ? C28 C33 C32 121.3(4) . . ? C28 C33 H33 119.4 . . ? C32 C33 H33 119.4 . . ? 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 -5.6(5) . . . . ? C22 O2 C2 C3 174.0(3) . . . . ? C6 C1 C2 O2 179.6(3) . . . . ? C6 C1 C2 C3 0.0(5) . . . . ? C23 O3 C3 C4 0.7(5) . . . . ? C23 O3 C3 C2 -179.6(3) . . . . ? O2 C2 C3 O3 -0.7(4) . . . . ? C1 C2 C3 O3 178.9(3) . . . . ? O2 C2 C3 C4 179.0(3) . . . . ? C1 C2 C3 C4 -1.4(5) . . . . ? O3 C3 C4 C5 -179.0(3) . . . . ? C2 C3 C4 C5 1.3(5) . . . . ? C3 C4 C5 C6 0.1(5) . . . . ? C3 C4 C5 C7 -174.8(3) . . . . ? C4 C5 C6 C1 -1.6(5) . . . . ? C7 C5 C6 C1 174.2(3) . . . . ? C4 C5 C6 N1 178.4(3) . . . . ? C7 C5 C6 N1 -5.8(4) . . . . ? C2 C1 C6 C5 1.5(5) . . . . ? C2 C1 C6 N1 -178.5(3) . . . . ? C9 N1 C6 C5 -159.7(3) . . . . ? C8 N1 C6 C5 -5.6(4) . . . . ? C9 N1 C6 C1 20.3(5) . . . . ? C8 N1 C6 C1 174.4(3) . . . . ? C6 C5 C7 C21 139.4(3) . . . . ? C4 C5 C7 C21 -45.4(5) . . . . ? C6 C5 C7 C8 14.0(4) . . . . ? C4 C5 C7 C8 -170.8(3) . . . . ? C6 C5 C7 C17 -105.5(3) . . . . ? C4 C5 C7 C17 69.8(5) . . . . ? C9 N1 C8 C18 45.0(4) . . . . ? C6 N1 C8 C18 -110.8(3) . . . . ? C9 N1 C8 C7 169.9(3) . . . . ? C6 N1 C8 C7 14.1(3) . . . . ? C5 C7 C8 N1 -16.4(3) . . . . ? C21 C7 C8 N1 -142.9(3) . . . . ? C17 C7 C8 N1 103.1(3) . . . . ? C5 C7 C8 C18 101.1(3) . . . . ? C21 C7 C8 C18 -25.3(4) . . . . ? C17 C7 C8 C18 -139.3(3) . . . . ? C6 N1 C9 O4 -24.3(5) . . . . ? C8 N1 C9 O4 -175.7(3) . . . . ? C6 N1 C9 C10 155.7(3) . . . . ? C8 N1 C9 C10 4.3(5) . . . . ? O4 C9 C10 C11 151.1(4) . . . . ? N1 C9 C10 C11 -28.9(5) . . . . ? C12 O1 C11 C18 -69.3(4) . . . . ? C12 O1 C11 C10 169.6(3) . . . . ? C9 C10 C11 O1 123.8(3) . . . . ? C9 C10 C11 C18 1.0(5) . . . . ? C11 O1 C12 C13 87.6(4) . . . . ? O1 C12 C13 C14 -62.0(6) . . . . ? C12 C13 C14 C19 -2.8(7) . . . . ? C12 C13 C14 C15 175.9(4) . . . . ? C16 N2 C15 C14 74.7(4) . . . . ? C21 N2 C15 C14 -46.3(5) . . . . ? C13 C14 C15 N2 -124.6(4) . . . . ? C19 C14 C15 N2 54.2(5) . . . . ? C15 N2 C16 C17 -142.1(3) . . . . ? C21 N2 C16 C17 -18.0(4) . . . . ? N2 C16 C17 C7 37.7(4) . . . . ? C5 C7 C17 C16 -166.5(3) . . . . ? C21 C7 C17 C16 -42.5(4) . . . . ? C8 C7 C17 C16 79.5(4) . . . . ? N1 C8 C18 C19 158.4(3) . . . . ? C7 C8 C18 C19 41.3(4) . . . . ? N1 C8 C18 C11 -70.4(3) . . . . ? C7 C8 C18 C11 172.5(3) . . . . ? O1 C11 C18 C8 -70.9(4) . . . . ? C10 C11 C18 C8 47.3(4) . . . . ? O1 C11 C18 C19 57.5(4) . . . . ? C10 C11 C18 C19 175.6(3) . . . . ? C13 C14 C19 C18 57.7(5) . . . . ? C15 C14 C19 C18 -121.0(4) . . . . ? C13 C14 C19 C20 175.9(4) . . . . ? C15 C14 C19 C20 -2.9(5) . . . . ? C8 C18 C19 C14 58.7(4) . . . . ? C11 C18 C19 C14 -67.0(4) . . . . ? C8 C18 C19 C20 -61.3(4) . . . . ? C11 C18 C19 C20 172.9(3) . . . . ? C14 C19 C20 C21 -55.5(4) . . . . ? C18 C19 C20 C21 68.7(4) . . . . ? C19 C20 C21 N2 63.5(4) . . . . ? C19 C20 C21 C7 -56.2(4) . . . . ? C16 N2 C21 C20 -134.5(3) . . . . ? C15 N2 C21 C20 -10.8(4) . . . . ? C16 N2 C21 C7 -8.7(4) . . . . ? C15 N2 C21 C7 114.9(4) . . . . ? C5 C7 C21 C20 -85.5(4) . . . . ? C8 C7 C21 C20 33.6(4) . . . . ? C17 C7 C21 C20 153.6(3) . . . . ? C5 C7 C21 N2 151.6(3) . . . . ? C8 C7 C21 N2 -89.4(4) . . . . ? C17 C7 C21 N2 30.7(3) . . . . ? C22A O2A C2A C1A -10.7(5) . . . . ? C22A O2A C2A C3A 168.1(3) . . . . ? C6A C1A C2A O2A -179.7(3) . . . . ? C6A C1A C2A C3A 1.6(5) . . . . ? C23A O3A C3A C4A 0.5(5) . . . . ? C23A O3A C3A C2A -179.9(3) . . . . ? O2A C2A C3A O3A -1.4(4) . . . . ? C1A C2A C3A O3A 177.4(3) . . . . ? O2A C2A C3A C4A 178.2(3) . . . . ? C1A C2A C3A C4A -3.0(5) . . . . ? O3A C3A C4A C5A -178.6(3) . . . . ? C2A C3A C4A C5A 1.9(5) . . . . ? C3A C4A C5A C6A 0.6(5) . . . . ? C3A C4A C5A C7A -174.0(3) . . . . ? C4A C5A C6A C1A -2.2(5) . . . . ? C7A C5A C6A C1A 173.4(3) . . . . ? C4A C5A C6A N1A 178.2(3) . . . . ? C7A C5A C6A N1A -6.3(4) . . . . ? C2A C1A C6A C5A 1.0(5) . . . . ? C2A C1A C6A N1A -179.3(3) . . . . ? C9A N1A C6A C5A -159.4(4) . . . . ? C8A N1A C6A C5A -5.1(4) . . . . ? C9A N1A C6A C1A 20.9(6) . . . . ? C8A N1A C6A C1A 175.2(3) . . . . ? C6A C5A C7A C17A -105.1(4) . . . . ? C4A C5A C7A C17A 70.0(5) . . . . ? C6A C5A C7A C21A 139.1(3) . . . . ? C4A C5A C7A C21A -45.9(5) . . . . ? C6A C5A C7A C8A 14.4(4) . . . . ? C4A C5A C7A C8A -170.6(4) . . . . ? C9A N1A C8A C18A 45.7(4) . . . . ? C6A N1A C8A C18A -110.5(3) . . . . ? C9A N1A C8A C7A 169.9(3) . . . . ? C6A N1A C8A C7A 13.7(4) . . . . ? C5A C7A C8A N1A -16.3(3) . . . . ? C17A C7A C8A N1A 102.9(3) . . . . ? C21A C7A C8A N1A -141.7(3) . . . . ? C5A C7A C8A C18A 100.4(4) . . . . ? C17A C7A C8A C18A -140.4(3) . . . . ? C21A C7A C8A C18A -25.0(5) . . . . ? C6A N1A C9A O4A -24.0(6) . . . . ? C8A N1A C9A O4A -176.0(3) . . . . ? C6A N1A C9A C10A 156.8(3) . . . . ? C8A N1A C9A C10A 4.9(5) . . . . ? O4A C9A C10A C11A 149.7(4) . . . . ? N1A C9A C10A C11A -31.2(5) . . . . ? C12A O1A C11A C10A 171.1(3) . . . . ? C12A O1A C11A C18A -67.7(4) . . . . ? C9A C10A C11A O1A 126.1(3) . . . . ? C9A C10A C11A C18A 3.0(5) . . . . ? C11A O1A C12A C13A 88.4(4) . . . . ? O1A C12A C13A C14A -65.1(5) . . . . ? C12A C13A C14A C15A 177.8(4) . . . . ? C12A C13A C14A C19A -1.1(6) . . . . ? C13A C14A C15A N2A -125.2(4) . . . . ? C19A C14A C15A N2A 53.7(5) . . . . ? C16A N2A C15A C14A 76.8(4) . . . . ? C21A N2A C15A C14A -45.2(4) . . . . ? C15A N2A C16A C17A -139.0(3) . . . . ? C21A N2A C16A C17A -14.0(4) . . . . ? N2A C16A C17A C7A 34.1(4) . . . . ? C5A C7A C17A C16A -164.3(3) . . . . ? C21A C7A C17A C16A -40.7(3) . . . . ? C8A C7A C17A C16A 81.7(4) . . . . ? N1A C8A C18A C19A 156.4(3) . . . . ? C7A C8A C18A C19A 40.6(4) . . . . ? N1A C8A C18A C11A -71.2(4) . . . . ? C7A C8A C18A C11A 173.0(3) . . . . ? O1A C11A C18A C19A 57.5(5) . . . . ? C10A C11A C18A C19A 175.0(3) . . . . ? O1A C11A C18A C8A -71.2(4) . . . . ? C10A C11A C18A C8A 46.3(4) . . . . ? C8A C18A C19A C20A -61.4(4) . . . . ? C11A C18A C19A C20A 172.5(3) . . . . ? C8A C18A C19A C14A 58.9(4) . . . . ? C11A C18A C19A C14A -67.2(5) . . . . ? C13A C14A C19A C18A 56.8(5) . . . . ? C15A C14A C19A C18A -122.1(4) . . . . ? C13A C14A C19A C20A 176.1(4) . . . . ? C15A C14A C19A C20A -2.8(5) . . . . ? C18A C19A C20A C21A 68.6(4) . . . . ? C14A C19A C20A C21A -55.4(4) . . . . ? C19A C20A C21A N2A 63.6(4) . . . . ? C19A C20A C21A C7A -55.4(5) . . . . ? C15A N2A C21A C20A -11.9(4) . . . . ? C16A N2A C21A C20A -136.4(3) . . . . ? C15A N2A C21A C7A 113.4(3) . . . . ? C16A N2A C21A C7A -11.2(4) . . . . ? C5A C7A C21A C20A -85.6(4) . . . . ? C17A C7A C21A C20A 153.5(3) . . . . ? C8A C7A C21A C20A 32.9(4) . . . . ? C5A C7A C21A N2A 152.5(3) . . . . ? C17A C7A C21A N2A 31.7(3) . . . . ? C8A C7A C21A N2A -89.0(4) . . . . ? C27A N3A C25A C26A 81.2(8) . . . . ? C27A N3A C25A C24A -154.4(6) . . . . ? O6A C24A C25A N3A -1.0(9) . . . . ? O5A C24A C25A N3A -179.3(6) . . . . ? O6A C24A C25A C26A 122.5(7) . . . . ? O5A C24A C25A C26A -55.7(8) . . . . ? N3A C25A C26A O7A 62.3(8) . . . . ? C24A C25A C26A O7A -60.9(8) . . . . ? C25A N3A C27A O8A -4.1(11) . . . . ? C25A N3A C27A C28A 179.5(6) . . . . ? O8A C27A C28A C29A 26.4(9) . . . . ? N3A C27A C28A C29A -156.9(6) . . . . ? O8A C27A C28A C33A -154.5(6) . . . . ? N3A C27A C28A C33A 22.2(10) . . . . ? C33A C28A C29A C30A 1.0(9) . . . . ? C27A C28A C29A C30A -179.9(6) . . . . ? C28A C29A C30A C31A 2.2(9) . . . . ? C29A C30A C31A C32A -1.2(10) . . . . ? C29A C30A C31A N4A 173.7(5) . . . . ? O10A N4A C31A C32A 1.3(10) . . . . ? O9A N4A C31A C32A -173.9(6) . . . . ? O10A N4A C31A C30A -173.7(6) . . . . ? O9A N4A C31A C30A 11.1(9) . . . . ? C30A C31A C32A C33A -3.2(11) . . . . ? N4A C31A C32A C33A -177.6(6) . . . . ? C31A C32A C33A C28A 6.5(10) . . . . ? C29A C28A C33A C32A -5.4(10) . . . . ? C27A C28A C33A C32A 175.4(6) . . . . ? C27B N3B C25B C26B 79.6(14) . . . . ? C27B N3B C25B C24B -152.3(10) . . . . ? O6B C24B C25B N3B -8.8(18) . . . . ? O5B C24B C25B N3B 168.0(10) . . . . ? O6B C24B C25B C26B 117.8(15) . . . . ? O5B C24B C25B C26B -65.5(15) . . . . ? N3B C25B C26B O7B 58.2(14) . . . . ? C24B C25B C26B O7B -65.5(15) . . . . ? C25B N3B C27B O8B 1.6(17) . . . . ? C25B N3B C27B C28B -179.3(10) . . . . ? O8B C27B C28B C29B 16.4(18) . . . . ? N3B C27B C28B C29B -162.8(11) . . . . ? O8B C27B C28B C33B -157.9(12) . . . . ? N3B C27B C28B C33B 22.9(17) . . . . ? C33B C28B C29B C30B 2(2) . . . . ? C27B C28B C29B C30B -173.1(13) . . . . ? C28B C29B C30B C31B -0.4(19) . . . . ? C29B C30B C31B C32B -0.6(19) . . . . ? C29B C30B C31B N4B 174.3(10) . . . . ? O9B N4B C31B C32B 137.2(13) . . . . ? O10B N4B C31B C32B -19.6(17) . . . . ? O9B N4B C31B C30B -38.2(15) . . . . ? O10B N4B C31B C30B 165.0(12) . . . . ? C30B C31B C32B C33B 0(2) . . . . ? N4B C31B C32B C33B -174.6(11) . . . . ? C31B C32B C33B C28B 1(2) . . . . ? C29B C28B C33B C32B -1.8(19) . . . . ? C27B C28B C33B C32B 172.5(12) . . . . ? C27 N3 C25 C26 73.8(6) . . . . ? C27 N3 C25 C24 -160.5(4) . . . . ? O5 C24 C25 N3 -5.2(6) . . . . ? O6 C24 C25 N3 176.9(4) . . . . ? O5 C24 C25 C26 119.9(5) . . . . ? O6 C24 C25 C26 -58.0(6) . . . . ? N3 C25 C26 O7 60.6(5) . . . . ? C24 C25 C26 O7 -65.2(5) . . . . ? C25 N3 C27 O8 5.4(7) . . . . ? C25 N3 C27 C28 -172.7(4) . . . . ? O8 C27 C28 C33 167.4(5) . . . . ? N3 C27 C28 C33 -14.5(7) . . . . ? O8 C27 C28 C29 -11.6(7) . . . . ? N3 C27 C28 C29 166.5(4) . . . . ? C33 C28 C29 C30 3.8(6) . . . . ? C27 C28 C29 C30 -177.2(4) . . . . ? C28 C29 C30 C31 -2.8(6) . . . . ? C29 C30 C31 C32 -0.5(7) . . . . ? C29 C30 C31 N4 179.8(4) . . . . ? O9 N4 C31 C30 -172.4(4) . . . . ? O10 N4 C31 C30 6.1(6) . . . . ? O9 N4 C31 C32 7.9(6) . . . . ? O10 N4 C31 C32 -173.6(4) . . . . ? C30 C31 C32 C33 2.6(6) . . . . ? N4 C31 C32 C33 -177.6(4) . . . . ? C29 C28 C33 C32 -1.5(6) . . . . ? C27 C28 C33 C32 179.5(4) . . . . ? C31 C32 C33 C28 -1.6(6) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2 O5 0.93 2.02 2.933(5) 166.6 . N2 H2 O6 0.93 2.24 2.936(5) 131.4 . N2A H2A O5B 0.93 1.78 2.613(11) 148.1 . N2A H2A O5A 0.93 1.84 2.656(7) 145.5 . O7B H7B O1W 0.94 1.76 2.683(13) 167.6 . O7A H7A O1W 0.84 1.79 2.632(7) 178.7 . O1W H11W O6 0.86 1.83 2.668(5) 167.8 . O1W H12W O2W 0.87 1.90 2.749(5) 163.2 . O2W H21W O5 0.86 1.83 2.680(5) 170.6 1_655 O2W H22W O5W 0.87 1.95 2.773(6) 157.3 . O3W H31W O41W 0.93 1.71 2.636(10) 173.1 1_655 O3W H31W O4W 0.93 1.88 2.760(6) 157.1 1_655 O3W H32W O5A 0.87 1.89 2.680(8) 150.7 . O3W H32W O5B 0.87 2.03 2.860(12) 160.8 . O4W H41W O4 0.86 2.53 3.288(6) 148.0 2_556 O4W H42W O6A 0.86 2.19 2.795(8) 127.9 . O4W H42W O9 0.86 2.38 2.993(6) 128.8 1_656 O5W H51W O7 0.86 1.92 2.756(6) 162.9 1_655 O5W H52W O3W 0.86 1.96 2.745(5) 152.2 . O6W H62W O8A 0.87 1.93 2.804(7) 174.2 1_455 O7W H71W O3W 0.86 2.52 3.342(10) 159.2 1_455 O7W H72W O7A 0.86 2.37 3.170(12) 154.8 . O7 H7 O61W 0.87 1.62 2.448(11) 157.9 . O7 H7 O7W 0.87 1.89 2.742(8) 168.6 . N3 H3 O2W 0.88 2.31 3.151(5) 160.0 1_455 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.374 _refine_diff_density_min -0.261 _refine_diff_density_rms 0.054 # start Validation Reply Form _vrf_PLAT430_9 ; PROBLEM: Short Inter D...A Contact O7B .. O61W .. 2.32 Ang. RESPONSE: Both the hydroxyl group and water molecule are disordered over two positions ; _vrf_PLAT772_9 ; PROBLEM: Suspect O-H Bond in CIF: O41W -- H42W .. 1.32 Ang. RESPONSE: disordered water molecule ; # end Validation Reply Form #===== end data_10 _database_code_depnum_ccdc_archive 'CCDC 758151' #TrackingRef 'bialonska2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; brucinium N-(4-nitrobenzoyl)-L-serinate 3.11-hydrate ethanol 0.22-solvate ; _chemical_name_common ;brucinium N-(4-nitrobenzoyl)-L-serinate 3.11-hydrate ethanol 0.22-solvate ; _chemical_melting_point ? _chemical_formula_moiety ; C23 H27 N2 O4, C10 H9 N2 O6, 0.22(C2 H6 O), 3.11(H2 O) ; _chemical_formula_sum 'C33.44 H43.54 N4 O13.33' _chemical_formula_weight 714.82 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 17.499(4) _cell_length_b 12.426(4) _cell_length_c 23.627(5) _cell_angle_alpha 90.00 _cell_angle_beta 102.14(3) _cell_angle_gamma 90.00 _cell_volume 5023(2) _cell_formula_units_Z 6 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 4023 _cell_measurement_theta_min 2.85 _cell_measurement_theta_max 28.53 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.418 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2273 _exptl_absorpt_coefficient_mu 0.110 _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 33673 _diffrn_reflns_av_R_equivalents 0.1407 _diffrn_reflns_av_sigmaI/netI 0.3117 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 2.85 _diffrn_reflns_theta_max 26.00 _reflns_number_total 10332 _reflns_number_gt 4177 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET) (compiled May 8 2007,13:10:02) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET) (compiled May 8 2007,13:10:02) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET) (compiled May 8 2007,13:10:02) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0746P)^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 10332 _refine_ls_number_parameters 1446 _refine_ls_number_restraints 1135 _refine_ls_R_factor_all 0.2349 _refine_ls_R_factor_gt 0.1028 _refine_ls_wR_factor_ref 0.2203 _refine_ls_wR_factor_gt 0.1803 _refine_ls_goodness_of_fit_ref 1.004 _refine_ls_restrained_S_all 0.980 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.6040(4) -0.5538(6) 0.6057(3) 0.0201(16) Uani 1 1 d U . . O2 O 0.3432(4) 0.0345(6) 0.5812(3) 0.0251(18) Uani 1 1 d U . . O3 O 0.4692(5) 0.1418(6) 0.5836(3) 0.0257(17) Uani 1 1 d U . . O4 O 0.3752(4) -0.3616(6) 0.5965(3) 0.028(2) Uani 1 1 d U . . N1 N 0.4986(5) -0.2973(8) 0.6179(4) 0.0211(16) Uani 1 1 d U . . N2 N 0.7611(5) -0.2272(8) 0.6391(4) 0.0240(17) Uani 1 1 d U . . H24 H 0.7982 -0.1725 0.6448 0.029 Uiso 1 1 calc R . . C1 C 0.4098(7) -0.1349(10) 0.5995(5) 0.020(2) Uani 1 1 d U . . H1 H 0.3629 -0.1748 0.5974 0.024 Uiso 1 1 calc R . . C2 C 0.4090(7) -0.0235(10) 0.5905(5) 0.0236(18) Uani 1 1 d U . . C3 C 0.4773(7) 0.0328(10) 0.5939(5) 0.0228(18) Uani 1 1 d U . . C4 C 0.5497(7) -0.0200(9) 0.6077(5) 0.022(2) Uani 1 1 d U . . H4 H 0.5970 0.0196 0.6115 0.027 Uiso 1 1 calc R . . C5 C 0.5514(7) -0.1281(10) 0.6156(5) 0.0210(18) Uani 1 1 d U . . C6 C 0.4835(7) -0.1844(9) 0.6118(5) 0.0197(17) Uani 1 1 d U . . C7 C 0.6210(7) -0.2072(9) 0.6303(5) 0.0230(16) Uani 1 1 d U . . C8 C 0.5817(6) -0.3160(9) 0.6204(5) 0.0192(17) Uani 1 1 d U . . H8 H 0.6033 -0.3649 0.6535 0.023 Uiso 1 1 calc R . . C9 C 0.4443(7) -0.3774(9) 0.5996(5) 0.0175(19) Uani 1 1 d U . . C10 C 0.4731(6) -0.4827(9) 0.5830(5) 0.018(2) Uani 1 1 d U . . H10A H 0.4327 -0.5125 0.5511 0.021 Uiso 1 1 calc R . . H10B H 0.4769 -0.5319 0.6164 0.021 Uiso 1 1 calc R . . C11 C 0.5531(6) -0.4866(9) 0.5634(5) 0.0202(18) Uani 1 1 d U . . H11 H 0.5459 -0.5195 0.5240 0.024 Uiso 1 1 calc R . . C12 C 0.6747(6) -0.5850(9) 0.5896(5) 0.021(2) Uani 1 1 d U . . H12A H 0.6658 -0.5921 0.5470 0.025 Uiso 1 1 calc R . . H12B H 0.6920 -0.6556 0.6070 0.025 Uiso 1 1 calc R . . C13 C 0.7347(7) -0.5047(9) 0.6094(5) 0.020(2) Uani 1 1 d U . . H13 H 0.7791 -0.5273 0.6373 0.024 Uiso 1 1 calc R . . C14 C 0.7336(7) -0.4019(9) 0.5920(5) 0.0207(18) Uani 1 1 d U . . C15 C 0.7978(6) -0.3207(9) 0.6164(5) 0.021(2) Uani 1 1 d U . . H15A H 0.8370 -0.3541 0.6479 0.026 Uiso 1 1 calc R . . H15B H 0.8247 -0.2971 0.5856 0.026 Uiso 1 1 calc R . . C16 C 0.7405(6) -0.2484(9) 0.6983(5) 0.023(2) Uani 1 1 d U . . H16A H 0.7354 -0.3265 0.7047 0.028 Uiso 1 1 calc R . . H16B H 0.7813 -0.2188 0.7299 0.028 Uiso 1 1 calc R . . C17 C 0.6636(6) -0.1919(9) 0.6957(5) 0.022(2) Uani 1 1 d U . . H17A H 0.6715 -0.1147 0.7056 0.027 Uiso 1 1 calc R . . H17B H 0.6336 -0.2258 0.7221 0.027 Uiso 1 1 calc R . . C18 C 0.5864(6) -0.3717(9) 0.5628(5) 0.0183(17) Uani 1 1 d U . . H18 H 0.5487 -0.3321 0.5322 0.022 Uiso 1 1 calc R . . C19 C 0.6657(6) -0.3594(9) 0.5465(5) 0.0187(17) Uani 1 1 d U . . H19 H 0.6649 -0.3963 0.5088 0.022 Uiso 1 1 calc R . . C20 C 0.6779(7) -0.2376(9) 0.5399(5) 0.0184(19) Uani 1 1 d U . . H20A H 0.7243 -0.2254 0.5229 0.022 Uiso 1 1 calc R . . H20B H 0.6318 -0.2067 0.5133 0.022 Uiso 1 1 calc R . . C21 C 0.6892(6) -0.1823(10) 0.5979(5) 0.0217(18) Uani 1 1 d U . . H21 H 0.6947 -0.1028 0.5932 0.026 Uiso 1 1 calc R . . C22 C 0.2684(6) -0.0250(9) 0.5679(5) 0.023(3) Uani 1 1 d U . . H22A H 0.2249 0.0262 0.5594 0.035 Uiso 1 1 calc R . . H22B H 0.2635 -0.0692 0.6013 0.035 Uiso 1 1 calc R . . H22C H 0.2672 -0.0715 0.5342 0.035 Uiso 1 1 calc R . . C23 C 0.5391(7) 0.2044(10) 0.5873(5) 0.030(3) Uani 1 1 d U . . H23A H 0.5251 0.2798 0.5782 0.046 Uiso 1 1 calc R . . H23B H 0.5688 0.1767 0.5596 0.046 Uiso 1 1 calc R . . H23C H 0.5711 0.1996 0.6266 0.046 Uiso 1 1 calc R . . O1A O 0.6354(5) -0.5453(7) 0.2774(3) 0.0296(18) Uani 1 1 d U . . O2A O 0.3402(4) 0.0260(6) 0.2401(3) 0.0256(18) Uani 1 1 d U . . O3A O 0.4620(4) 0.1405(6) 0.2431(3) 0.0225(17) Uani 1 1 d U . . O4A O 0.3916(4) -0.3748(6) 0.2425(3) 0.0226(19) Uani 1 1 d U . . N1A N 0.5100(5) -0.3001(7) 0.2803(4) 0.0208(16) Uani 1 1 d U . . N2A N 0.7689(5) -0.2007(8) 0.3237(4) 0.0246(17) Uani 1 1 d U . . H24A H 0.8022 -0.1420 0.3328 0.029 Uiso 1 1 calc R . . C1A C 0.4139(7) -0.1429(10) 0.2607(5) 0.023(2) Uani 1 1 d U . . H1A H 0.3693 -0.1862 0.2609 0.027 Uiso 1 1 calc R . . C2A C 0.4077(7) -0.0322(10) 0.2507(5) 0.0222(18) Uani 1 1 d U . . C3A C 0.4761(6) 0.0322(10) 0.2535(5) 0.0227(18) Uani 1 1 d U . . C4A C 0.5498(7) -0.0152(9) 0.2680(5) 0.021(2) Uani 1 1 d U . . H4A H 0.5956 0.0273 0.2711 0.025 Uiso 1 1 calc R . . C5A C 0.5553(7) -0.1232(9) 0.2777(5) 0.0214(18) Uani 1 1 d U . . C6A C 0.4876(7) -0.1857(9) 0.2702(5) 0.0207(18) Uani 1 1 d U . . C7A C 0.6257(7) -0.1910(9) 0.3021(5) 0.0248(17) Uani 1 1 d U . . C8A C 0.5966(7) -0.3093(9) 0.2898(5) 0.0231(18) Uani 1 1 d U . . H8A H 0.6168 -0.3553 0.3244 0.028 Uiso 1 1 calc R . . C9A C 0.4630(7) -0.3827(10) 0.2583(5) 0.0213(19) Uani 1 1 d U . . C10A C 0.5065(7) -0.4862(9) 0.2548(5) 0.023(2) Uani 1 1 d U . . H10C H 0.4711 -0.5348 0.2282 0.028 Uiso 1 1 calc R . . H10D H 0.5161 -0.5200 0.2936 0.028 Uiso 1 1 calc R . . C11A C 0.5848(7) -0.4829(10) 0.2352(5) 0.0269(18) Uani 1 1 d U . . H11A H 0.5796 -0.5151 0.1957 0.032 Uiso 1 1 calc R . . C12A C 0.7136(7) -0.5641(10) 0.2680(5) 0.029(2) Uani 1 1 d U . . H12C H 0.7114 -0.5702 0.2259 0.035 Uiso 1 1 calc R . . H12D H 0.7334 -0.6332 0.2862 0.035 Uiso 1 1 calc R . . C13A C 0.7688(7) -0.4765(10) 0.2923(5) 0.027(2) Uani 1 1 d U . . H13A H 0.8132 -0.4946 0.3214 0.032 Uiso 1 1 calc R . . C14A C 0.7599(7) -0.3766(10) 0.2760(5) 0.0248(18) Uani 1 1 d U . . C15A C 0.8141(7) -0.2882(10) 0.3049(5) 0.026(2) Uani 1 1 d U . . H15C H 0.8512 -0.3180 0.3388 0.032 Uiso 1 1 calc R . . H15D H 0.8447 -0.2598 0.2774 0.032 Uiso 1 1 calc R . . C16A C 0.7360(6) -0.2259(10) 0.3767(5) 0.028(2) Uani 1 1 d U . . H16C H 0.7319 -0.3046 0.3816 0.034 Uiso 1 1 calc R . . H16D H 0.7701 -0.1957 0.4119 0.034 Uiso 1 1 calc R . . C17A C 0.6562(7) -0.1744(10) 0.3660(5) 0.025(2) Uani 1 1 d U . . H17C H 0.6223 -0.2102 0.3890 0.030 Uiso 1 1 calc R . . H17D H 0.6600 -0.0969 0.3759 0.030 Uiso 1 1 calc R . . C18A C 0.6130(7) -0.3627(10) 0.2360(5) 0.0245(18) Uani 1 1 d U . . H18A H 0.5770 -0.3272 0.2027 0.029 Uiso 1 1 calc R . . C19A C 0.6941(7) -0.3401(10) 0.2271(5) 0.0256(18) Uani 1 1 d U . . H19A H 0.7005 -0.3773 0.1909 0.031 Uiso 1 1 calc R . . C20A C 0.7023(7) -0.2221(9) 0.2187(5) 0.026(2) Uani 1 1 d U . . H20C H 0.6595 -0.1961 0.1873 0.032 Uiso 1 1 calc R . . H20D H 0.7527 -0.2065 0.2077 0.032 Uiso 1 1 calc R . . C21A C 0.6986(7) -0.1639(10) 0.2769(5) 0.0255(18) Uani 1 1 d U . . H21A H 0.7015 -0.0843 0.2715 0.031 Uiso 1 1 calc R . . C22A C 0.2679(6) -0.0350(10) 0.2385(6) 0.033(3) Uani 1 1 d U . . H22D H 0.2229 0.0138 0.2291 0.049 Uiso 1 1 calc R . . H22E H 0.2695 -0.0680 0.2764 0.049 Uiso 1 1 calc R . . H22F H 0.2629 -0.0913 0.2089 0.049 Uiso 1 1 calc R . . C23A C 0.5293(6) 0.2058(9) 0.2431(5) 0.023(3) Uani 1 1 d U . . H23D H 0.5131 0.2807 0.2349 0.034 Uiso 1 1 calc R . . H23E H 0.5561 0.1799 0.2132 0.034 Uiso 1 1 calc R . . H23F H 0.5649 0.2015 0.2811 0.034 Uiso 1 1 calc R . . O1B O 0.3765(4) -0.5228(6) 0.0593(3) 0.0179(16) Uani 1 1 d U . . O2B O 0.6564(4) 0.0629(6) 0.1015(3) 0.0186(17) Uani 1 1 d U . . O3B O 0.5305(4) 0.1697(6) 0.0935(3) 0.0193(17) Uani 1 1 d U . . O4B O 0.6140(4) -0.3398(6) 0.0889(3) 0.023(2) Uani 1 1 d U . . N1B N 0.4965(5) -0.2660(7) 0.0494(4) 0.0160(16) Uani 1 1 d U . . N2B N 0.2361(5) -0.1824(7) 0.0066(4) 0.0168(16) Uani 1 1 d U . . H24B H 0.2002 -0.1263 -0.0016 0.020 Uiso 1 1 calc R . . C1B C 0.5860(7) -0.1046(9) 0.0744(5) 0.0159(19) Uani 1 1 d U . . H1B H 0.6324 -0.1447 0.0750 0.019 Uiso 1 1 calc R . . C2B C 0.5900(7) 0.0034(9) 0.0870(5) 0.0184(18) Uani 1 1 d U . . C3B C 0.5223(7) 0.0621(9) 0.0812(5) 0.0199(18) Uani 1 1 d U . . C4B C 0.4465(7) 0.0140(9) 0.0635(5) 0.019(2) Uani 1 1 d U . . H4B H 0.3998 0.0547 0.0593 0.023 Uiso 1 1 calc R . . C5B C 0.4459(6) -0.0943(9) 0.0529(5) 0.0158(17) Uani 1 1 d U . . C6B C 0.5153(7) -0.1532(9) 0.0611(5) 0.0161(17) Uani 1 1 d U . . C7B C 0.3770(6) -0.1640(9) 0.0289(5) 0.0146(16) Uani 1 1 d U . . C8B C 0.4098(6) -0.2805(9) 0.0415(5) 0.0145(17) Uani 1 1 d U . . H8B H 0.3898 -0.3282 0.0075 0.017 Uiso 1 1 calc R . . C9B C 0.5431(7) -0.3452(9) 0.0729(5) 0.0179(19) Uani 1 1 d U . . C10B C 0.5030(6) -0.4557(8) 0.0740(5) 0.016(2) Uani 1 1 d U . . H10E H 0.5396 -0.5056 0.0988 0.019 Uiso 1 1 calc R . . H10F H 0.4910 -0.4859 0.0343 0.019 Uiso 1 1 calc R . . C11B C 0.4266(6) -0.4483(9) 0.0969(5) 0.0177(18) Uani 1 1 d U . . H11B H 0.4367 -0.4771 0.1374 0.021 Uiso 1 1 calc R . . C12B C 0.2989(6) -0.5418(9) 0.0762(5) 0.018(2) Uani 1 1 d U . . H12E H 0.2806 -0.6162 0.0663 0.021 Uiso 1 1 calc R . . H12F H 0.3042 -0.5314 0.1184 0.021 Uiso 1 1 calc R . . C13B C 0.2421(6) -0.4627(9) 0.0436(5) 0.0147(19) Uani 1 1 d U . . H13B H 0.2016 -0.4866 0.0128 0.018 Uiso 1 1 calc R . . C14B C 0.2480(6) -0.3604(9) 0.0572(5) 0.0132(17) Uani 1 1 d U . . C15B C 0.1917(6) -0.2768(8) 0.0241(5) 0.0136(19) Uani 1 1 d U . . H15E H 0.1596 -0.3104 -0.0110 0.016 Uiso 1 1 calc R . . H15F H 0.1562 -0.2512 0.0487 0.016 Uiso 1 1 calc R . . C16B C 0.2639(6) -0.2028(9) -0.0478(5) 0.0150(19) Uani 1 1 d U . . H16E H 0.2276 -0.1711 -0.0814 0.018 Uiso 1 1 calc R . . H16F H 0.2683 -0.2810 -0.0544 0.018 Uiso 1 1 calc R . . C17B C 0.3444(6) -0.1484(9) -0.0383(4) 0.0147(19) Uani 1 1 d U . . H17E H 0.3395 -0.0711 -0.0488 0.018 Uiso 1 1 calc R . . H17F H 0.3784 -0.1840 -0.0612 0.018 Uiso 1 1 calc R . . C18B C 0.3948(6) -0.3326(9) 0.0972(5) 0.0151(17) Uani 1 1 d U . . H18B H 0.4298 -0.2947 0.1301 0.018 Uiso 1 1 calc R . . C19B C 0.3115(6) -0.3144(9) 0.1052(5) 0.0137(17) Uani 1 1 d U . . H19B H 0.3063 -0.3478 0.1427 0.016 Uiso 1 1 calc R . . C20B C 0.3022(6) -0.1934(9) 0.1099(5) 0.0156(19) Uani 1 1 d U . . H20E H 0.2521 -0.1773 0.1214 0.019 Uiso 1 1 calc R . . H20F H 0.3452 -0.1644 0.1401 0.019 Uiso 1 1 calc R . . C21B C 0.3034(6) -0.1400(9) 0.0523(5) 0.0148(17) Uani 1 1 d U . . H21B H 0.2977 -0.0604 0.0561 0.018 Uiso 1 1 calc R . . C22B C 0.7288(6) 0.0029(9) 0.1036(5) 0.020(3) Uani 1 1 d U . . H22G H 0.7736 0.0513 0.1150 0.030 Uiso 1 1 calc R . . H22H H 0.7289 -0.0274 0.0653 0.030 Uiso 1 1 calc R . . H22I H 0.7325 -0.0556 0.1319 0.030 Uiso 1 1 calc R . . C23B C 0.4624(7) 0.2378(9) 0.0903(6) 0.026(3) Uani 1 1 d U . . H23G H 0.4792 0.3124 0.0986 0.039 Uiso 1 1 calc R . . H23H H 0.4327 0.2135 0.1188 0.039 Uiso 1 1 calc R . . H23I H 0.4293 0.2334 0.0514 0.039 Uiso 1 1 calc R . . O5 O 0.8550(6) -0.0689(8) 0.6262(5) 0.069(3) Uani 1 1 d U . . O6 O 0.9202(7) -0.1123(10) 0.7165(6) 0.084(4) Uani 1 1 d U . . O7 O 1.0411(6) 0.0081(9) 0.6199(5) 0.071(3) Uani 1 1 d U . . O8 O 0.9947(6) 0.2462(8) 0.7242(5) 0.062(3) Uani 1 1 d U . . O9 O 1.2687(6) 0.2662(8) 0.9832(4) 0.050(3) Uani 1 1 d U . . O10 O 1.2680(6) 0.0931(8) 0.9871(4) 0.054(3) Uani 1 1 d U . . N3 N 1.0026(6) 0.0723(11) 0.7277(6) 0.060(4) Uani 1 1 d U . . H37 H 1.0261 0.0150 0.7451 0.072 Uiso 1 1 calc R . . N4 N 1.2436(7) 0.1781(12) 0.9624(5) 0.048(3) Uani 1 1 d U . . C24 C 0.9024(8) -0.0593(11) 0.6730(7) 0.042(4) Uani 1 1 d DU . . C25 C 0.9440(10) 0.0578(12) 0.6743(7) 0.071(5) Uani 1 1 d DU . . H25 H 0.9026 0.1133 0.6741 0.086 Uiso 1 1 calc R . . C26 C 0.9783(9) 0.0777(13) 0.6210(7) 0.064(5) Uani 1 1 d U . . H26A H 0.9372 0.0668 0.5856 0.077 Uiso 1 1 calc R . . H26B H 0.9965 0.1532 0.6212 0.077 Uiso 1 1 calc R . . C27 C 1.0215(8) 0.1671(12) 0.7507(7) 0.038(4) Uani 1 1 d U . . C28 C 1.0782(8) 0.1625(13) 0.8046(7) 0.051(4) Uani 1 1 d U . . C29 C 1.0978(8) 0.2541(11) 0.8392(6) 0.036(4) Uani 1 1 d U . . H29 H 1.0681 0.3166 0.8260 0.043 Uiso 1 1 calc R . . C30 C 1.1502(7) 0.2665(11) 0.8863(6) 0.034(4) Uani 1 1 d U . . H30 H 1.1612 0.3349 0.9042 0.040 Uiso 1 1 calc R . . C31 C 1.1888(7) 0.1758(10) 0.9086(6) 0.027(3) Uani 1 1 d U . . C32 C 1.1725(9) 0.0797(13) 0.8802(7) 0.051(4) Uani 1 1 d U . . H32 H 1.1981 0.0169 0.8977 0.061 Uiso 1 1 calc R . . C33 C 1.1215(8) 0.0692(11) 0.8279(6) 0.041(4) Uani 1 1 d U . . H33 H 1.1150 0.0024 0.8079 0.049 Uiso 1 1 calc R . . O5A O -0.109(2) -0.063(2) 0.3682(12) 0.048(12) Uani 0.477(13) 1 d PDU A 1 O6A O -0.1195(10) 0.1108(13) 0.3484(8) 0.042(6) Uani 0.477(13) 1 d PDU A 1 O61A O -0.1358(8) -0.0089(12) 0.2595(7) 0.032(5) Uani 0.523(13) 1 d PDU A 2 O51A O -0.1128(14) -0.0799(17) 0.3500(9) 0.010(5) Uani 0.523(13) 1 d PDU A 2 C241 C -0.0917(12) -0.040(2) 0.3062(8) 0.050(9) Uani 0.523(13) 1 d PDU A 2 O7A O 0.0920(6) 0.0560(9) 0.2665(5) 0.078(4) Uani 1 1 d U . . O8A O 0.0707(7) -0.0021(10) 0.4429(5) 0.092(4) Uani 1 1 d U A . O9A O 0.3069(6) -0.4744(8) 0.4795(4) 0.058(3) Uani 1 1 d U . . O10A O 0.2368(7) -0.4963(10) 0.5466(5) 0.087(4) Uani 1 1 d U . . N3A N 0.0480(7) -0.0842(10) 0.3528(6) 0.061(4) Uani 1 1 d U A . H37A H 0.0593 -0.1352 0.3335 0.073 Uiso 1 1 d . . . N4A N 0.2551(7) -0.4533(10) 0.5052(5) 0.039(3) Uani 1 1 d U A . C24A C -0.0831(14) 0.0224(15) 0.3494(13) 0.048(9) Uani 0.477(13) 1 d PDU A 1 C25A C -0.0042(10) 0.0099(18) 0.3240(9) 0.104(7) Uani 1 1 d DU . . H25A H 0.0215 0.0760 0.3428 0.125 Uiso 1 1 d . . . C26A C 0.0140(11) 0.0166(16) 0.2633(9) 0.090(6) Uani 1 1 d U A . H26C H 0.0109 -0.0484 0.2400 0.108 Uiso 1 1 d . . . H26D H -0.0186 0.0716 0.2343 0.108 Uiso 1 1 d . . . C27A C 0.0742(10) -0.0792(14) 0.4125(9) 0.067(5) Uani 1 1 d U . . C28A C 0.1296(8) -0.1772(12) 0.4376(7) 0.044(4) Uani 1 1 d U A . C29A C 0.1678(8) -0.2283(12) 0.4056(7) 0.052(4) Uani 1 1 d U . . H29A H 0.1660 -0.2071 0.3667 0.063 Uiso 1 1 calc R A . C30A C 0.2128(8) -0.3173(11) 0.4301(7) 0.049(4) Uani 1 1 d U A . H30A H 0.2450 -0.3541 0.4087 0.059 Uiso 1 1 calc R . . C31A C 0.2099(7) -0.3505(11) 0.4848(6) 0.033(4) Uani 1 1 d U . . C32A C 0.1657(8) -0.2968(13) 0.5190(6) 0.054(4) Uani 1 1 d U A . H32A H 0.1625 -0.3211 0.5565 0.065 Uiso 1 1 calc R . . C33A C 0.1237(9) -0.1978(13) 0.4920(7) 0.056(5) Uani 1 1 d U . . H33A H 0.0948 -0.1528 0.5124 0.068 Uiso 1 1 calc R A . O5B O -0.1082(5) -0.5656(7) 0.0167(4) 0.035(2) Uani 1 1 d U . . O6B O -0.1488(5) -0.5250(7) -0.0764(4) 0.041(3) Uani 1 1 d U . . O7B O 0.0840(5) -0.4518(7) -0.0825(3) 0.039(2) Uani 1 1 d U . . O8B O -0.0108(4) -0.2926(7) 0.0471(3) 0.029(2) Uani 1 1 d U . . O9B O 0.2575(5) -0.2805(7) 0.3027(4) 0.033(2) Uani 1 1 d U . . O10B O 0.2612(5) -0.4558(7) 0.3075(4) 0.036(2) Uani 1 1 d U . . N3B N 0.0295(5) -0.4571(7) 0.0259(4) 0.013(2) Uani 1 1 d U . . H37B H 0.0600 -0.5124 0.0380 0.016 Uiso 1 1 calc R . . N4B N 0.2361(6) -0.3685(10) 0.2821(5) 0.033(3) Uani 1 1 d U . . C24B C -0.1013(7) -0.5226(10) -0.0300(6) 0.029(3) Uani 1 1 d DU . . C25B C -0.0201(6) -0.4601(10) -0.0300(5) 0.028(3) Uani 1 1 d DU . . H25B H -0.0338 -0.3840 -0.0416 0.034 Uiso 1 1 calc R . . C26B C 0.0167(7) -0.5104(10) -0.0778(5) 0.027(3) Uani 1 1 d U . . H26E H 0.0308 -0.5863 -0.0681 0.032 Uiso 1 1 calc R . . H26F H -0.0215 -0.5089 -0.1152 0.032 Uiso 1 1 calc R . . C27B C 0.0307(6) -0.3746(10) 0.0593(5) 0.020(3) Uani 1 1 d U . . C28B C 0.0826(6) -0.3779(10) 0.1203(5) 0.020(2) Uani 1 1 d U . . C29B C 0.1228(6) -0.4730(10) 0.1439(5) 0.026(2) Uani 1 1 d U . . H29B H 0.1159 -0.5374 0.1218 0.031 Uiso 1 1 calc R . . C30B C 0.1710(7) -0.4738(10) 0.1977(5) 0.028(2) Uani 1 1 d U . . H30B H 0.1934 -0.5384 0.2153 0.033 Uiso 1 1 calc R . . C31B C 0.1852(7) -0.3754(10) 0.2251(5) 0.025(2) Uani 1 1 d U . . C32B C 0.1480(6) -0.2820(10) 0.2034(5) 0.024(2) Uani 1 1 d U . . H32B H 0.1566 -0.2165 0.2245 0.028 Uiso 1 1 calc R . . C33B C 0.0982(6) -0.2870(10) 0.1506(5) 0.020(2) Uani 1 1 d U . . H33B H 0.0734 -0.2225 0.1347 0.024 Uiso 1 1 calc R . . O11 O 0.9326(7) -0.1766(11) 0.4580(6) 0.033(4) Uani 0.624(14) 1 d PU B 1 O11A O 0.9257(12) -0.1246(18) 0.5003(10) 0.035(5) Uani 0.376(14) 1 d PU B 2 O12 O 0.2627(10) -0.4017(15) 0.7329(9) 0.019(5) Uani 0.397(14) 1 d PU C 1 O12A O 0.2695(7) -0.3771(11) 0.6861(6) 0.021(3) Uani 0.603(14) 1 d PU C 2 O13 O -0.0541(6) 0.2763(9) 0.1124(4) 0.069(3) Uani 1 1 d U . . O14 O 0.9178(6) -0.2683(10) 0.8019(5) 0.085(4) Uani 1 1 d U . . O15 O 0.6995(6) 0.2237(9) 0.1870(5) 0.075(4) Uani 1 1 d U . . O16 O 0.1059(5) 0.3318(7) 0.0372(3) 0.033(2) Uani 1 1 d U . . O17 O 0.8426(5) 0.3108(8) 0.1888(4) 0.058(3) Uani 1 1 d U . . O18 O 0.1085(7) 0.1119(12) 0.5381(6) 0.116(5) Uani 1 1 d U . . O34 O -0.1844(9) -0.3292(13) -0.1214(7) 0.066(6) Uani 0.668(16) 1 d PU D 1 C34 C -0.2671(12) -0.3133(18) -0.1338(9) 0.045(7) Uani 0.668(16) 1 d PU D 1 C35 C -0.3256(15) -0.243(2) -0.1727(12) 0.081(9) Uani 0.668(16) 1 d PU D 1 O19 O -0.1977(12) -0.2252(18) -0.1384(9) 0.018(8) Uani 0.332(16) 1 d PU D 2 O21 O 0.935(3) -0.686(4) 0.284(2) 0.114(8) Uani 0.34(3) 1 d PU E 1 O21A O 0.8969(16) -0.6799(18) 0.3114(12) 0.114(8) Uani 0.66(3) 1 d PU E 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 0.021(3) 0.023(3) 0.018(3) 0.000(3) 0.007(3) 0.000(3) O2 0.027(4) 0.025(4) 0.024(4) 0.001(3) 0.007(3) -0.005(3) O3 0.040(4) 0.015(4) 0.023(4) -0.005(3) 0.009(3) -0.006(3) O4 0.023(5) 0.018(5) 0.043(5) -0.011(4) 0.006(4) 0.002(4) N1 0.021(3) 0.019(3) 0.026(3) -0.001(3) 0.010(3) 0.005(3) N2 0.024(3) 0.022(3) 0.028(3) -0.003(3) 0.008(3) -0.001(3) C1 0.021(4) 0.024(4) 0.018(4) 0.000(4) 0.010(4) -0.007(4) C2 0.028(4) 0.024(4) 0.020(3) -0.001(3) 0.008(3) -0.005(3) C3 0.034(4) 0.019(3) 0.016(3) -0.002(3) 0.009(3) -0.007(3) C4 0.032(4) 0.020(4) 0.017(4) -0.001(4) 0.009(4) -0.009(4) C5 0.027(3) 0.018(3) 0.020(3) -0.003(3) 0.009(3) -0.005(3) C6 0.023(3) 0.018(3) 0.020(3) -0.001(3) 0.011(3) 0.000(3) C7 0.026(3) 0.019(3) 0.027(3) 0.002(3) 0.011(3) -0.001(3) C8 0.019(3) 0.016(3) 0.025(3) 0.001(3) 0.012(3) 0.001(3) C9 0.016(4) 0.017(4) 0.022(4) -0.001(4) 0.010(3) 0.003(3) C10 0.019(4) 0.017(4) 0.021(4) -0.001(4) 0.010(3) 0.000(4) C11 0.019(3) 0.019(3) 0.023(3) 0.000(3) 0.006(3) 0.001(3) C12 0.021(4) 0.022(4) 0.020(4) 0.001(4) 0.005(4) 0.000(4) C13 0.021(4) 0.022(4) 0.018(4) -0.001(4) 0.009(4) -0.001(4) C14 0.023(4) 0.021(4) 0.019(4) -0.001(3) 0.008(3) -0.002(3) C15 0.021(4) 0.021(4) 0.024(4) -0.001(4) 0.011(4) 0.000(3) C16 0.023(4) 0.020(4) 0.029(4) 0.000(4) 0.010(4) -0.002(4) C17 0.025(4) 0.016(4) 0.029(4) 0.002(4) 0.013(4) -0.001(4) C18 0.017(3) 0.017(3) 0.023(3) 0.003(3) 0.008(3) -0.003(3) C19 0.020(3) 0.020(3) 0.019(3) 0.001(3) 0.011(3) 0.000(3) C20 0.017(4) 0.022(4) 0.021(4) 0.004(4) 0.016(3) -0.001(3) C21 0.022(3) 0.021(3) 0.025(3) 0.002(3) 0.010(3) -0.003(3) C22 0.024(6) 0.029(7) 0.015(6) -0.004(5) 0.001(5) 0.004(5) C23 0.042(7) 0.023(6) 0.030(6) -0.007(6) 0.016(6) 0.001(6) O1A 0.036(4) 0.027(4) 0.028(4) 0.006(3) 0.012(3) 0.011(3) O2A 0.018(4) 0.022(4) 0.035(4) -0.001(3) 0.002(3) -0.004(3) O3A 0.014(4) 0.024(4) 0.033(4) 0.002(4) 0.015(3) 0.009(3) O4A 0.021(4) 0.022(5) 0.029(5) -0.001(4) 0.014(4) -0.014(4) N1A 0.025(3) 0.016(3) 0.024(3) 0.006(3) 0.011(3) 0.000(3) N2A 0.023(4) 0.025(4) 0.030(4) 0.010(3) 0.012(3) 0.003(3) C1A 0.020(4) 0.020(4) 0.028(4) 0.001(4) 0.006(4) -0.001(4) C2A 0.018(3) 0.020(3) 0.030(4) 0.001(3) 0.005(3) 0.000(3) C3A 0.018(3) 0.021(3) 0.031(4) 0.002(3) 0.010(3) 0.004(3) C4A 0.019(4) 0.018(4) 0.029(4) 0.004(4) 0.013(4) 0.004(4) C5A 0.020(3) 0.018(3) 0.028(3) 0.008(3) 0.009(3) 0.004(3) C6A 0.020(3) 0.017(3) 0.027(3) 0.003(3) 0.009(3) 0.000(3) C7A 0.025(3) 0.020(3) 0.029(3) 0.010(3) 0.006(3) 0.006(3) C8A 0.027(3) 0.019(3) 0.025(3) 0.008(3) 0.009(3) 0.004(3) C9A 0.028(4) 0.016(4) 0.022(4) 0.007(4) 0.010(4) -0.004(4) C10A 0.031(4) 0.018(4) 0.021(4) 0.008(4) 0.007(4) 0.003(4) C11A 0.034(4) 0.024(4) 0.024(4) 0.008(3) 0.008(3) 0.008(3) C12A 0.035(4) 0.029(4) 0.028(4) 0.004(4) 0.018(4) 0.014(4) C13A 0.027(4) 0.029(4) 0.030(4) 0.005(4) 0.022(4) 0.012(4) C14A 0.025(4) 0.027(4) 0.028(4) 0.008(3) 0.020(3) 0.007(3) C15A 0.025(4) 0.029(4) 0.030(4) 0.008(4) 0.018(4) 0.002(4) C16A 0.027(4) 0.025(4) 0.032(4) 0.003(4) 0.006(4) 0.007(4) C17A 0.026(4) 0.018(4) 0.030(4) 0.002(4) 0.007(4) 0.008(4) C18A 0.029(3) 0.023(3) 0.024(3) 0.007(3) 0.010(3) 0.009(3) C19A 0.027(3) 0.025(4) 0.029(4) 0.008(3) 0.016(3) 0.010(3) C20A 0.025(4) 0.022(4) 0.035(4) 0.011(4) 0.012(4) 0.013(4) C21A 0.024(4) 0.022(4) 0.032(4) 0.011(3) 0.009(3) 0.008(3) C22A 0.024(6) 0.030(7) 0.040(7) 0.000(6) -0.001(6) -0.025(5) C23A 0.012(6) 0.017(6) 0.041(7) 0.004(6) 0.012(5) 0.008(5) O1B 0.020(3) 0.011(3) 0.023(4) 0.000(3) 0.004(3) 0.000(3) O2B 0.020(4) 0.016(4) 0.021(4) -0.005(3) 0.005(3) -0.003(3) O3B 0.022(4) 0.015(4) 0.023(4) -0.009(3) 0.009(3) -0.002(3) O4B 0.025(5) 0.022(5) 0.020(5) -0.006(4) 0.001(4) 0.002(4) N1B 0.018(3) 0.011(3) 0.017(3) -0.001(3) -0.001(3) -0.004(3) N2B 0.016(3) 0.017(3) 0.018(3) -0.001(3) 0.005(3) 0.000(3) C1B 0.019(4) 0.016(4) 0.014(4) -0.001(4) 0.006(3) -0.001(3) C2B 0.020(3) 0.018(3) 0.018(3) -0.001(3) 0.004(3) -0.001(3) C3B 0.023(3) 0.017(3) 0.020(3) -0.002(3) 0.006(3) -0.002(3) C4B 0.023(4) 0.017(4) 0.018(4) -0.002(4) 0.002(4) 0.000(4) C5B 0.019(3) 0.012(3) 0.015(3) 0.002(3) 0.001(3) -0.003(3) C6B 0.021(3) 0.013(3) 0.015(3) 0.000(3) 0.003(3) -0.002(3) C7B 0.016(3) 0.013(3) 0.015(3) 0.004(3) 0.002(3) -0.003(3) C8B 0.016(3) 0.012(3) 0.015(3) -0.003(3) 0.003(3) -0.001(3) C9B 0.021(4) 0.012(4) 0.020(4) -0.003(3) 0.002(4) 0.000(3) C10B 0.021(4) 0.007(4) 0.020(4) 0.001(4) 0.003(4) 0.007(4) C11B 0.022(3) 0.011(3) 0.021(3) 0.001(3) 0.006(3) 0.006(3) C12B 0.018(4) 0.013(4) 0.021(4) -0.006(4) 0.003(4) -0.001(3) C13B 0.016(4) 0.015(4) 0.014(4) -0.006(4) 0.005(3) -0.005(4) C14B 0.013(3) 0.015(3) 0.013(3) 0.000(3) 0.007(3) -0.004(3) C15B 0.013(4) 0.016(4) 0.013(4) 0.000(3) 0.006(3) -0.003(3) C16B 0.014(4) 0.016(4) 0.018(4) 0.000(4) 0.009(3) -0.006(3) C17B 0.012(4) 0.017(4) 0.016(4) 0.004(4) 0.005(3) -0.006(3) C18B 0.017(3) 0.013(3) 0.016(3) 0.001(3) 0.004(3) 0.002(3) C19B 0.014(3) 0.015(3) 0.013(3) 0.001(3) 0.005(3) -0.001(3) C20B 0.013(4) 0.019(4) 0.014(4) 0.005(4) 0.001(3) 0.005(3) C21B 0.014(3) 0.016(3) 0.013(3) 0.002(3) 0.000(3) 0.002(3) C22B 0.021(6) 0.016(6) 0.024(6) -0.002(5) 0.007(5) -0.007(5) C23B 0.027(7) 0.009(6) 0.043(7) -0.002(6) 0.008(6) 0.000(5) O5 0.057(6) 0.050(6) 0.094(7) 0.005(6) 0.002(6) 0.006(5) O6 0.082(7) 0.078(7) 0.095(8) 0.006(6) 0.024(6) -0.015(6) O7 0.048(6) 0.063(6) 0.094(7) -0.016(6) -0.005(5) 0.020(5) O8 0.074(7) 0.045(6) 0.072(7) 0.006(5) 0.025(6) 0.014(5) O9 0.062(6) 0.039(6) 0.051(6) -0.010(5) 0.015(5) 0.009(5) O10 0.060(6) 0.043(6) 0.067(6) 0.020(5) 0.028(5) 0.001(5) N3 0.024(6) 0.067(8) 0.083(8) -0.005(7) -0.002(6) -0.015(6) N4 0.055(7) 0.052(7) 0.045(7) 0.013(6) 0.030(6) 0.006(6) C24 0.040(7) 0.051(8) 0.036(8) 0.011(7) 0.011(7) 0.019(6) C25 0.074(9) 0.071(9) 0.069(9) -0.002(8) 0.015(8) -0.016(7) C26 0.055(8) 0.053(8) 0.077(9) -0.005(7) -0.005(7) 0.001(7) C27 0.039(7) 0.031(7) 0.049(8) -0.002(7) 0.019(6) -0.003(6) C28 0.041(7) 0.059(8) 0.058(8) 0.009(7) 0.023(7) -0.009(7) C29 0.034(7) 0.035(7) 0.047(8) -0.004(6) 0.029(6) 0.010(6) C30 0.028(7) 0.033(7) 0.043(7) 0.007(6) 0.014(6) 0.003(6) C31 0.035(7) 0.014(6) 0.039(7) -0.001(6) 0.022(6) 0.004(5) C32 0.053(8) 0.053(8) 0.048(8) 0.010(7) 0.014(7) 0.013(7) C33 0.040(7) 0.033(7) 0.057(8) 0.003(6) 0.025(6) 0.016(6) O5A 0.040(13) 0.055(14) 0.050(14) -0.002(9) 0.011(9) 0.007(9) O6A 0.028(9) 0.032(9) 0.060(10) 0.013(8) 0.000(7) -0.002(7) O61A 0.015(8) 0.028(8) 0.046(9) 0.000(7) -0.010(6) -0.004(6) O51A 0.008(8) 0.013(8) 0.010(9) 0.003(7) 0.000(7) -0.001(6) C241 0.050(12) 0.042(12) 0.056(12) -0.004(9) 0.006(9) -0.004(9) O7A 0.075(7) 0.084(7) 0.083(7) -0.012(6) 0.031(6) -0.010(6) O8A 0.086(7) 0.083(7) 0.102(8) -0.025(7) 0.007(6) 0.033(6) O9A 0.069(6) 0.044(6) 0.052(6) -0.026(5) -0.008(5) 0.014(5) O10A 0.083(7) 0.080(7) 0.084(7) 0.035(6) -0.015(6) -0.021(6) N3A 0.048(7) 0.052(7) 0.068(8) -0.008(6) -0.021(6) 0.006(6) N4A 0.032(6) 0.040(7) 0.037(7) -0.006(6) -0.011(5) -0.013(5) C24A 0.039(12) 0.050(12) 0.057(13) 0.000(9) 0.019(9) -0.005(9) C25A 0.078(10) 0.111(11) 0.125(11) 0.008(9) 0.023(8) 0.005(8) C26A 0.080(9) 0.085(10) 0.099(10) -0.004(8) 0.006(8) -0.014(8) C27A 0.065(9) 0.045(8) 0.080(9) -0.012(8) -0.008(7) -0.005(7) C28A 0.040(7) 0.044(8) 0.042(8) -0.012(7) -0.002(6) -0.009(6) C29A 0.040(8) 0.047(8) 0.067(8) -0.004(7) 0.004(7) -0.011(7) C30A 0.038(7) 0.035(7) 0.073(9) 0.014(7) 0.007(7) 0.008(6) C31A 0.027(7) 0.029(7) 0.040(7) 0.000(6) -0.004(6) 0.009(6) C32A 0.054(8) 0.065(8) 0.043(8) -0.005(7) 0.008(7) -0.009(7) C33A 0.053(8) 0.061(8) 0.054(8) -0.018(7) 0.007(7) 0.004(7) O5B 0.030(5) 0.041(5) 0.035(5) -0.001(5) 0.008(4) -0.012(4) O6B 0.031(5) 0.040(5) 0.044(6) 0.010(5) -0.008(4) -0.018(4) O7B 0.027(5) 0.064(6) 0.025(5) -0.008(4) 0.003(4) -0.018(4) O8B 0.023(5) 0.034(5) 0.033(5) 0.006(4) 0.012(4) 0.008(4) O9B 0.034(5) 0.026(5) 0.036(5) -0.004(4) 0.002(4) -0.004(4) O10B 0.036(5) 0.029(5) 0.041(5) -0.002(5) 0.005(4) 0.013(4) N3B 0.012(5) 0.011(5) 0.014(5) 0.006(4) -0.004(4) -0.001(4) N4B 0.031(6) 0.032(6) 0.032(6) -0.006(6) -0.001(5) 0.004(5) C24B 0.030(7) 0.022(6) 0.034(7) 0.009(6) 0.001(6) -0.009(5) C25B 0.034(7) 0.024(6) 0.027(7) 0.013(6) 0.008(6) -0.002(6) C26B 0.034(7) 0.027(7) 0.024(6) -0.003(6) 0.017(5) -0.016(5) C27B 0.013(6) 0.018(6) 0.026(7) 0.005(6) 0.001(5) -0.009(5) C28B 0.011(4) 0.023(4) 0.029(4) 0.003(4) 0.016(3) 0.002(3) C29B 0.020(4) 0.026(4) 0.034(4) 0.002(4) 0.009(3) 0.004(4) C30B 0.025(4) 0.025(4) 0.032(4) 0.004(4) 0.005(3) 0.006(4) C31B 0.022(4) 0.024(4) 0.031(4) 0.002(4) 0.007(3) 0.003(4) C32B 0.019(4) 0.025(4) 0.029(4) 0.001(4) 0.009(3) -0.001(4) C33B 0.015(4) 0.026(4) 0.025(4) 0.001(4) 0.016(3) -0.001(4) O11 0.032(6) 0.031(7) 0.026(7) -0.015(6) -0.019(5) -0.002(5) O11A 0.030(8) 0.042(8) 0.026(8) -0.013(7) -0.005(7) 0.014(7) O12 0.018(7) 0.015(7) 0.022(8) 0.002(6) -0.002(6) 0.007(6) O12A 0.024(6) 0.022(6) 0.025(7) -0.005(6) 0.020(5) -0.006(5) O13 0.056(6) 0.080(7) 0.061(6) -0.024(6) -0.007(5) 0.025(5) O14 0.077(7) 0.096(7) 0.072(7) -0.014(6) -0.006(6) 0.010(6) O15 0.059(6) 0.081(7) 0.090(7) -0.050(6) 0.029(6) -0.023(5) O16 0.028(5) 0.030(5) 0.035(5) -0.018(4) -0.009(4) 0.004(4) O17 0.063(6) 0.040(6) 0.075(6) -0.003(5) 0.027(5) 0.003(5) O18 0.094(7) 0.119(8) 0.133(8) -0.036(7) 0.019(7) 0.024(7) O34 0.051(8) 0.068(10) 0.072(9) -0.001(7) -0.006(7) 0.000(7) C34 0.037(10) 0.053(10) 0.044(10) -0.003(8) 0.004(8) 0.010(8) C35 0.080(12) 0.086(13) 0.081(12) 0.002(9) 0.025(9) -0.004(9) O19 0.025(11) 0.011(11) 0.011(10) -0.005(8) -0.009(8) -0.003(8) O21 0.114(10) 0.110(9) 0.116(10) -0.007(7) 0.016(7) -0.004(7) O21A 0.113(10) 0.108(9) 0.117(10) -0.007(7) 0.015(7) -0.004(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C12 1.423(12) . ? O1 C11 1.454(12) . ? O2 C2 1.336(13) . ? O2 C22 1.478(12) . ? O3 C3 1.378(13) . ? O3 C23 1.437(13) . ? O4 C9 1.211(12) . ? N1 C9 1.382(14) . ? N1 C6 1.430(14) . ? N1 C8 1.462(13) . ? N2 C15 1.481(13) . ? N2 C21 1.524(14) . ? N2 C16 1.538(14) . ? N2 H24 0.9300 . ? C1 C2 1.400(15) . ? C1 C6 1.403(15) . ? C1 H1 0.9500 . ? C2 C3 1.372(15) . ? C3 C4 1.403(15) . ? C4 C5 1.356(15) . ? C4 H4 0.9500 . ? C5 C6 1.366(15) . ? C5 C7 1.546(15) . ? C7 C8 1.513(15) . ? C7 C21 1.579(15) . ? C7 C17 1.579(15) . ? C8 C18 1.543(14) . ? C8 H8 1.0000 . ? C9 C10 1.483(15) . ? C10 C11 1.565(14) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C18 1.544(15) . ? C11 H11 1.0000 . ? C12 C13 1.453(14) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.340(15) . ? C13 H13 0.9500 . ? C14 C19 1.519(15) . ? C14 C15 1.530(15) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 C17 1.508(14) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 C19 1.524(14) . ? C18 H18 1.0000 . ? C19 C20 1.541(15) . ? C19 H19 1.0000 . ? C20 C21 1.509(15) . ? 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 . ? O1A C11A 1.417(13) . ? O1A C12A 1.451(13) . ? O2A C2A 1.363(12) . ? O2A C22A 1.469(12) . ? O3A C3A 1.381(13) . ? O3A C23A 1.430(12) . ? O4A C9A 1.231(12) . ? N1A C9A 1.349(14) . ? N1A C6A 1.481(14) . ? N1A C8A 1.488(14) . ? N2A C15A 1.467(13) . ? N2A C16A 1.516(14) . ? N2A C21A 1.541(14) . ? N2A H24A 0.9300 . ? C1A C6A 1.369(15) . ? C1A C2A 1.396(15) . ? C1A H1A 0.9500 . ? C2A C3A 1.430(15) . ? C3A C4A 1.392(14) . ? C4A C5A 1.361(14) . ? C4A H4A 0.9500 . ? C5A C6A 1.397(15) . ? C5A C7A 1.504(15) . ? C7A C17A 1.507(15) . ? C7A C21A 1.554(15) . ? C7A C8A 1.564(16) . ? C8A C18A 1.515(15) . ? C8A H8A 1.0000 . ? C9A C10A 1.505(15) . ? C10A C11A 1.538(15) . ? C10A H10C 0.9900 . ? C10A H10D 0.9900 . ? C11A C18A 1.572(16) . ? C11A H11A 1.0000 . ? C12A C13A 1.488(17) . ? C12A H12C 0.9900 . ? C12A H12D 0.9900 . ? C13A C14A 1.299(16) . ? C13A H13A 0.9500 . ? C14A C15A 1.518(16) . ? C14A C19A 1.518(15) . ? C15A H15C 0.9900 . ? C15A H15D 0.9900 . ? C16A C17A 1.508(14) . ? C16A H16C 0.9900 . ? C16A H16D 0.9900 . ? C17A H17C 0.9900 . ? C17A H17D 0.9900 . ? C18A C19A 1.505(15) . ? C18A H18A 1.0000 . ? C19A C20A 1.490(15) . ? C19A H19A 1.0000 . ? C20A C21A 1.568(16) . ? C20A H20C 0.9900 . ? C20A H20D 0.9900 . ? C21A H21A 1.0000 . ? C22A H22D 0.9800 . ? C22A H22E 0.9800 . ? C22A H22F 0.9800 . ? C23A H23D 0.9800 . ? C23A H23E 0.9800 . ? C23A H23F 0.9800 . ? O1B C11B 1.446(12) . ? O1B C12B 1.513(12) . ? O2B C2B 1.360(12) . ? O2B C22B 1.463(12) . ? O3B C3B 1.369(13) . ? O3B C23B 1.450(12) . ? O4B C9B 1.221(12) . ? N1B C9B 1.324(14) . ? N1B C6B 1.452(13) . ? N1B C8B 1.500(13) . ? N2B C16B 1.488(12) . ? N2B C15B 1.511(12) . ? N2B C21B 1.515(13) . ? N2B H24B 0.9300 . ? C1B C6B 1.354(14) . ? C1B C2B 1.372(14) . ? C1B H1B 0.9500 . ? C2B C3B 1.373(15) . ? C3B C4B 1.435(14) . ? C4B C5B 1.369(15) . ? C4B H4B 0.9500 . ? C5B C6B 1.395(15) . ? C5B C7B 1.496(14) . ? C7B C21B 1.535(14) . ? C7B C8B 1.562(15) . ? C7B C17B 1.583(14) . ? C8B C18B 1.538(14) . ? C8B H8B 1.0000 . ? C9B C10B 1.544(15) . ? C10B C11B 1.548(14) . ? C10B H10E 0.9900 . ? C10B H10F 0.9900 . ? C11B C18B 1.542(14) . ? C11B H11B 1.0000 . ? C12B C13B 1.490(14) . ? C12B H12E 0.9900 . ? C12B H12F 0.9900 . ? C13B C14B 1.310(14) . ? C13B H13B 0.9500 . ? C14B C19B 1.522(14) . ? C14B C15B 1.529(14) . ? C15B H15E 0.9900 . ? C15B H15F 0.9900 . ? C16B C17B 1.537(13) . ? C16B H16E 0.9900 . ? C16B H16F 0.9900 . ? C17B H17E 0.9900 . ? C17B H17F 0.9900 . ? C18B C19B 1.525(14) . ? C18B H18B 1.0000 . ? C19B C20B 1.519(15) . ? C19B H19B 1.0000 . ? C20B C21B 1.518(14) . ? C20B H20E 0.9900 . ? C20B H20F 0.9900 . ? C21B H21B 1.0000 . ? C22B H22G 0.9800 . ? C22B H22H 0.9800 . ? C22B H22I 0.9800 . ? C23B H23G 0.9800 . ? C23B H23H 0.9800 . ? C23B H23I 0.9800 . ? O5 C24 1.240(16) . ? O6 C24 1.205(15) . ? O7 C26 1.403(15) . ? O8 C27 1.208(15) . ? O9 N4 1.241(14) . ? O10 N4 1.238(14) . ? N3 C27 1.311(16) . ? N3 C25 1.460(18) . ? N3 H37 0.8800 . ? N4 C31 1.422(16) . ? C24 C25 1.625(12) . ? C25 C26 1.52(2) . ? C25 H25 1.0000 . ? C26 H26A 0.9900 . ? C26 H26B 0.9900 . ? C27 C28 1.441(19) . ? C28 C29 1.401(19) . ? C28 C33 1.430(18) . ? C29 C30 1.294(16) . ? C29 H29 0.9500 . ? C30 C31 1.363(16) . ? C30 H30 0.9500 . ? C31 C32 1.370(18) . ? C32 C33 1.369(17) . ? C32 H32 0.9500 . ? C33 H33 0.9500 . ? O5A C24A 1.268(11) . ? O6A C24A 1.268(11) . ? O61A C241 1.268(11) . ? O51A C241 1.267(11) . ? C241 C25A 1.624(12) . ? O7A C26A 1.437(19) . ? O8A C27A 1.206(18) . ? O9A N4A 1.220(13) . ? O10A N4A 1.216(14) . ? N3A C27A 1.389(19) . ? N3A C25A 1.55(2) . ? N3A H37A 0.8299 . ? N4A C31A 1.527(16) . ? C24A C25A 1.626(12) . ? C25A C26A 1.53(2) . ? C25A H25A 0.9961 . ? C26A H26C 0.9722 . ? C26A H26D 1.0480 . ? C27A C28A 1.59(2) . ? C28A C29A 1.279(18) . ? C28A C33A 1.337(18) . ? C29A C30A 1.409(18) . ? C29A H29A 0.9500 . ? C30A C31A 1.368(18) . ? C30A H30A 0.9500 . ? C31A C32A 1.399(17) . ? C32A C33A 1.50(2) . ? C32A H32A 0.9500 . ? C33A H33A 0.9500 . ? O5B C24B 1.253(14) . ? O6B C24B 1.228(14) . ? O7B C26B 1.410(12) . ? O8B C27B 1.249(13) . ? O9B N4B 1.224(12) . ? O10B N4B 1.273(12) . ? N3B C27B 1.290(14) . ? N3B C25B 1.421(12) . ? N3B H37B 0.8800 . ? N4B C31B 1.451(14) . ? C24B C25B 1.620(11) . ? C25B C26B 1.544(15) . ? C25B H25B 1.0000 . ? C26B H26E 0.9900 . ? C26B H26F 0.9900 . ? C27B C28B 1.534(15) . ? C28B C33B 1.335(15) . ? C28B C29B 1.428(15) . ? C29B C30B 1.370(15) . ? C29B H29B 0.9500 . ? C30B C31B 1.381(16) . ? C30B H30B 0.9500 . ? C31B C32B 1.375(16) . ? C32B C33B 1.365(15) . ? C32B H32B 0.9500 . ? C33B H33B 0.9500 . ? O34 C34 1.43(2) . ? C34 C35 1.50(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C12 O1 C11 114.4(8) . . ? C2 O2 C22 117.4(9) . . ? C3 O3 C23 117.9(10) . . ? C9 N1 C6 125.1(10) . . ? C9 N1 C8 120.8(9) . . ? C6 N1 C8 108.8(9) . . ? C15 N2 C21 114.8(9) . . ? C15 N2 C16 113.4(9) . . ? C21 N2 C16 108.9(8) . . ? C15 N2 H24 106.4 . . ? C21 N2 H24 106.4 . . ? C16 N2 H24 106.4 . . ? C2 C1 C6 116.3(11) . . ? C2 C1 H1 121.8 . . ? C6 C1 H1 121.8 . . ? O2 C2 C3 116.4(11) . . ? O2 C2 C1 122.6(11) . . ? C3 C2 C1 121.0(12) . . ? C2 C3 O3 115.8(11) . . ? C2 C3 C4 120.5(12) . . ? O3 C3 C4 123.7(11) . . ? C5 C4 C3 119.2(12) . . ? C5 C4 H4 120.4 . . ? C3 C4 H4 120.4 . . ? C4 C5 C6 120.3(12) . . ? C4 C5 C7 130.8(11) . . ? C6 C5 C7 108.8(10) . . ? C5 C6 C1 122.6(11) . . ? C5 C6 N1 110.8(11) . . ? C1 C6 N1 126.4(11) . . ? C8 C7 C5 102.9(9) . . ? C8 C7 C21 117.7(10) . . ? C5 C7 C21 114.0(10) . . ? C8 C7 C17 111.4(9) . . ? C5 C7 C17 109.3(9) . . ? C21 C7 C17 101.6(9) . . ? N1 C8 C7 106.2(9) . . ? N1 C8 C18 105.9(9) . . ? C7 C8 C18 115.5(9) . . ? N1 C8 H8 109.7 . . ? C7 C8 H8 109.7 . . ? C18 C8 H8 109.7 . . ? O4 C9 N1 121.0(11) . . ? O4 C9 C10 121.1(11) . . ? N1 C9 C10 117.9(10) . . ? C9 C10 C11 118.7(9) . . ? C9 C10 H10A 107.6 . . ? C11 C10 H10A 107.6 . . ? C9 C10 H10B 107.6 . . ? C11 C10 H10B 107.6 . . ? H10A C10 H10B 107.1 . . ? O1 C11 C18 111.1(9) . . ? O1 C11 C10 105.7(9) . . ? C18 C11 C10 109.7(9) . . ? O1 C11 H11 110.1 . . ? C18 C11 H11 110.1 . . ? C10 C11 H11 110.1 . . ? O1 C12 C13 109.7(9) . . ? 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 126.4(11) . . ? C14 C13 H13 116.8 . . ? C12 C13 H13 116.8 . . ? C13 C14 C19 120.4(11) . . ? C13 C14 C15 123.5(11) . . ? C19 C14 C15 116.1(10) . . ? N2 C15 C14 108.3(9) . . ? N2 C15 H15A 110.0 . . ? C14 C15 H15A 110.0 . . ? N2 C15 H15B 110.0 . . ? C14 C15 H15B 110.0 . . ? H15A C15 H15B 108.4 . . ? C17 C16 N2 105.1(9) . . ? C17 C16 H16A 110.7 . . ? N2 C16 H16A 110.7 . . ? C17 C16 H16B 110.7 . . ? N2 C16 H16B 110.7 . . ? H16A C16 H16B 108.8 . . ? C16 C17 C7 102.6(9) . . ? 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 113.5(9) . . ? C19 C18 C11 117.4(9) . . ? C8 C18 C11 108.4(9) . . ? C19 C18 H18 105.5 . . ? C8 C18 H18 105.5 . . ? C11 C18 H18 105.5 . . ? C14 C19 C18 113.9(9) . . ? C14 C19 C20 108.0(9) . . ? C18 C19 C20 106.0(9) . . ? C14 C19 H19 109.6 . . ? C18 C19 H19 109.6 . . ? C20 C19 H19 109.6 . . ? C21 C20 C19 110.5(9) . . ? C21 C20 H20A 109.6 . . ? C19 C20 H20A 109.6 . . ? C21 C20 H20B 109.6 . . ? C19 C20 H20B 109.6 . . ? H20A C20 H20B 108.1 . . ? C20 C21 N2 110.3(9) . . ? C20 C21 C7 112.5(9) . . ? N2 C21 C7 103.0(9) . . ? C20 C21 H21 110.3 . . ? N2 C21 H21 110.3 . . ? C7 C21 H21 110.3 . . ? 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 . . ? C11A O1A C12A 116.8(9) . . ? C2A O2A C22A 116.1(9) . . ? C3A O3A C23A 115.8(8) . . ? C9A N1A C6A 123.3(10) . . ? C9A N1A C8A 121.2(10) . . ? C6A N1A C8A 109.0(9) . . ? C15A N2A C16A 114.8(9) . . ? C15A N2A C21A 113.8(9) . . ? C16A N2A C21A 105.6(8) . . ? C15A N2A H24A 107.4 . . ? C16A N2A H24A 107.4 . . ? C21A N2A H24A 107.4 . . ? C6A C1A C2A 116.6(11) . . ? C6A C1A H1A 121.7 . . ? C2A C1A H1A 121.7 . . ? O2A C2A C1A 126.0(11) . . ? O2A C2A C3A 113.3(10) . . ? C1A C2A C3A 120.6(11) . . ? O3A C3A C4A 125.3(10) . . ? O3A C3A C2A 114.9(10) . . ? C4A C3A C2A 119.8(11) . . ? C5A C4A C3A 119.2(11) . . ? C5A C4A H4A 120.4 . . ? C3A C4A H4A 120.4 . . ? C4A C5A C6A 119.9(11) . . ? C4A C5A C7A 129.8(11) . . ? C6A C5A C7A 110.0(10) . . ? C1A C6A C5A 123.3(11) . . ? C1A C6A N1A 127.5(11) . . ? C5A C6A N1A 108.9(10) . . ? C5A C7A C17A 113.4(10) . . ? C5A C7A C21A 113.8(10) . . ? C17A C7A C21A 102.0(10) . . ? C5A C7A C8A 104.3(10) . . ? C17A C7A C8A 110.4(10) . . ? C21A C7A C8A 113.2(10) . . ? N1A C8A C18A 105.9(9) . . ? N1A C8A C7A 103.8(9) . . ? C18A C8A C7A 117.2(10) . . ? N1A C8A H8A 109.9 . . ? C18A C8A H8A 109.9 . . ? C7A C8A H8A 109.9 . . ? O4A C9A N1A 123.7(11) . . ? O4A C9A C10A 123.0(11) . . ? N1A C9A C10A 113.4(10) . . ? C9A C10A C11A 119.1(10) . . ? C9A C10A H10C 107.5 . . ? C11A C10A H10C 107.5 . . ? C9A C10A H10D 107.5 . . ? C11A C10A H10D 107.5 . . ? H10C C10A H10D 107.0 . . ? O1A C11A C10A 103.7(9) . . ? O1A C11A C18A 111.3(10) . . ? C10A C11A C18A 108.6(9) . . ? O1A C11A H11A 111.0 . . ? C10A C11A H11A 111.0 . . ? C18A C11A H11A 111.0 . . ? O1A C12A C13A 112.3(10) . . ? O1A C12A H12C 109.1 . . ? C13A C12A H12C 109.1 . . ? O1A C12A H12D 109.1 . . ? C13A C12A H12D 109.1 . . ? H12C C12A H12D 107.9 . . ? C14A C13A C12A 123.8(12) . . ? C14A C13A H13A 118.1 . . ? C12A C13A H13A 118.1 . . ? C13A C14A C15A 122.2(12) . . ? C13A C14A C19A 122.4(12) . . ? C15A C14A C19A 115.4(11) . . ? N2A C15A C14A 110.3(9) . . ? N2A C15A H15C 109.6 . . ? C14A C15A H15C 109.6 . . ? N2A C15A H15D 109.6 . . ? C14A C15A H15D 109.6 . . ? H15C C15A H15D 108.1 . . ? C17A C16A N2A 105.9(9) . . ? C17A C16A H16C 110.6 . . ? N2A C16A H16C 110.6 . . ? C17A C16A H16D 110.6 . . ? N2A C16A H16D 110.6 . . ? H16C C16A H16D 108.7 . . ? C7A C17A C16A 103.3(10) . . ? C7A C17A H17C 111.1 . . ? C16A C17A H17C 111.1 . . ? C7A C17A H17D 111.1 . . ? C16A C17A H17D 111.1 . . ? H17C C17A H17D 109.1 . . ? C19A C18A C8A 112.7(10) . . ? C19A C18A C11A 118.6(10) . . ? C8A C18A C11A 108.2(10) . . ? C19A C18A H18A 105.4 . . ? C8A C18A H18A 105.4 . . ? C11A C18A H18A 105.4 . . ? C20A C19A C18A 108.8(10) . . ? C20A C19A C14A 108.5(10) . . ? C18A C19A C14A 115.1(10) . . ? C20A C19A H19A 108.1 . . ? C18A C19A H19A 108.1 . . ? C14A C19A H19A 108.1 . . ? C19A C20A C21A 108.3(10) . . ? C19A C20A H20C 110.0 . . ? C21A C20A H20C 110.0 . . ? C19A C20A H20D 110.0 . . ? C21A C20A H20D 110.0 . . ? H20C C20A H20D 108.4 . . ? N2A C21A C7A 104.9(9) . . ? N2A C21A C20A 108.6(9) . . ? C7A C21A C20A 115.2(10) . . ? N2A C21A H21A 109.3 . . ? C7A C21A H21A 109.3 . . ? C20A C21A H21A 109.3 . . ? O2A C22A H22D 109.5 . . ? O2A C22A H22E 109.5 . . ? H22D C22A H22E 109.5 . . ? O2A C22A H22F 109.5 . . ? H22D C22A H22F 109.5 . . ? H22E C22A H22F 109.5 . . ? O3A C23A H23D 109.5 . . ? O3A C23A H23E 109.5 . . ? H23D C23A H23E 109.5 . . ? O3A C23A H23F 109.5 . . ? H23D C23A H23F 109.5 . . ? H23E C23A H23F 109.5 . . ? C11B O1B C12B 113.5(8) . . ? C2B O2B C22B 114.8(8) . . ? C3B O3B C23B 120.7(9) . . ? C9B N1B C6B 122.9(9) . . ? C9B N1B C8B 118.7(9) . . ? C6B N1B C8B 108.8(9) . . ? C16B N2B C15B 112.5(8) . . ? C16B N2B C21B 109.2(8) . . ? C15B N2B C21B 116.2(8) . . ? C16B N2B H24B 106.1 . . ? C15B N2B H24B 106.1 . . ? C21B N2B H24B 106.1 . . ? C6B C1B C2B 119.3(11) . . ? C6B C1B H1B 120.4 . . ? C2B C1B H1B 120.4 . . ? O2B C2B C1B 126.1(11) . . ? O2B C2B C3B 114.1(10) . . ? C1B C2B C3B 119.6(11) . . ? O3B C3B C2B 116.7(10) . . ? O3B C3B C4B 121.2(10) . . ? C2B C3B C4B 122.2(11) . . ? C5B C4B C3B 115.8(11) . . ? C5B C4B H4B 122.1 . . ? C3B C4B H4B 122.1 . . ? C4B C5B C6B 121.1(11) . . ? C4B C5B C7B 127.8(10) . . ? C6B C5B C7B 111.0(10) . . ? C1B C6B C5B 121.6(11) . . ? C1B C6B N1B 129.4(11) . . ? C5B C6B N1B 108.9(10) . . ? C5B C7B C21B 115.0(9) . . ? C5B C7B C8B 103.3(9) . . ? C21B C7B C8B 114.5(9) . . ? C5B C7B C17B 113.6(9) . . ? C21B C7B C17B 100.7(8) . . ? C8B C7B C17B 110.2(9) . . ? N1B C8B C18B 107.1(8) . . ? N1B C8B C7B 103.5(8) . . ? C18B C8B C7B 115.5(9) . . ? N1B C8B H8B 110.1 . . ? C18B C8B H8B 110.1 . . ? C7B C8B H8B 110.1 . . ? O4B C9B N1B 125.8(11) . . ? O4B C9B C10B 118.6(10) . . ? N1B C9B C10B 115.3(10) . . ? C9B C10B C11B 112.4(9) . . ? C9B C10B H10E 109.1 . . ? C11B C10B H10E 109.1 . . ? C9B C10B H10F 109.1 . . ? C11B C10B H10F 109.1 . . ? H10E C10B H10F 107.9 . . ? O1B C11B C18B 115.3(9) . . ? O1B C11B C10B 101.7(8) . . ? C18B C11B C10B 113.4(9) . . ? O1B C11B H11B 108.7 . . ? C18B C11B H11B 108.7 . . ? C10B C11B H11B 108.7 . . ? C13B C12B O1B 107.4(8) . . ? C13B C12B H12E 110.2 . . ? O1B C12B H12E 110.2 . . ? C13B C12B H12F 110.2 . . ? O1B C12B H12F 110.2 . . ? H12E C12B H12F 108.5 . . ? C14B C13B C12B 120.2(10) . . ? C14B C13B H13B 119.9 . . ? C12B C13B H13B 119.9 . . ? C13B C14B C19B 123.7(10) . . ? C13B C14B C15B 121.6(10) . . ? C19B C14B C15B 114.6(9) . . ? N2B C15B C14B 110.8(8) . . ? N2B C15B H15E 109.5 . . ? C14B C15B H15E 109.5 . . ? N2B C15B H15F 109.5 . . ? C14B C15B H15F 109.5 . . ? H15E C15B H15F 108.1 . . ? N2B C16B C17B 104.8(8) . . ? N2B C16B H16E 110.8 . . ? C17B C16B H16E 110.8 . . ? N2B C16B H16F 110.8 . . ? C17B C16B H16F 110.8 . . ? H16E C16B H16F 108.9 . . ? C16B C17B C7B 102.6(8) . . ? C16B C17B H17E 111.3 . . ? C7B C17B H17E 111.3 . . ? C16B C17B H17F 111.3 . . ? C7B C17B H17F 111.3 . . ? H17E C17B H17F 109.2 . . ? C19B C18B C8B 112.4(9) . . ? C19B C18B C11B 119.6(9) . . ? C8B C18B C11B 105.2(9) . . ? C19B C18B H18B 106.3 . . ? C8B C18B H18B 106.3 . . ? C11B C18B H18B 106.3 . . ? C20B C19B C14B 110.7(9) . . ? C20B C19B C18B 106.1(9) . . ? C14B C19B C18B 114.8(9) . . ? C20B C19B H19B 108.3 . . ? C14B C19B H19B 108.3 . . ? C18B C19B H19B 108.3 . . ? C21B C20B C19B 110.2(9) . . ? C21B C20B H20E 109.6 . . ? C19B C20B H20E 109.6 . . ? C21B C20B H20F 109.6 . . ? C19B C20B H20F 109.6 . . ? H20E C20B H20F 108.1 . . ? N2B C21B C20B 109.4(9) . . ? N2B C21B C7B 105.1(8) . . ? C20B C21B C7B 114.1(9) . . ? N2B C21B H21B 109.3 . . ? C20B C21B H21B 109.3 . . ? C7B C21B H21B 109.3 . . ? O2B C22B H22G 109.5 . . ? O2B C22B H22H 109.5 . . ? H22G C22B H22H 109.5 . . ? O2B C22B H22I 109.5 . . ? H22G C22B H22I 109.5 . . ? H22H C22B H22I 109.5 . . ? O3B C23B H23G 109.5 . . ? O3B C23B H23H 109.5 . . ? H23G C23B H23H 109.5 . . ? O3B C23B H23I 109.5 . . ? H23G C23B H23I 109.5 . . ? H23H C23B H23I 109.5 . . ? C27 N3 C25 122.7(14) . . ? C27 N3 H37 118.7 . . ? C25 N3 H37 118.7 . . ? O10 N4 O9 120.5(13) . . ? O10 N4 C31 120.2(13) . . ? O9 N4 C31 119.2(12) . . ? O6 C24 O5 135.3(15) . . ? O6 C24 C25 116.1(15) . . ? O5 C24 C25 108.4(13) . . ? N3 C25 C26 111.6(13) . . ? N3 C25 C24 110.9(13) . . ? C26 C25 C24 112.5(14) . . ? N3 C25 H25 107.2 . . ? C26 C25 H25 107.2 . . ? C24 C25 H25 107.2 . . ? O7 C26 C25 111.2(14) . . ? O7 C26 H26A 109.4 . . ? C25 C26 H26A 109.4 . . ? O7 C26 H26B 109.4 . . ? C25 C26 H26B 109.4 . . ? H26A C26 H26B 108.0 . . ? O8 C27 N3 118.6(15) . . ? O8 C27 C28 127.7(15) . . ? N3 C27 C28 113.5(14) . . ? C29 C28 C33 112.9(14) . . ? C29 C28 C27 121.4(14) . . ? C33 C28 C27 125.6(15) . . ? C30 C29 C28 129.8(15) . . ? C30 C29 H29 115.1 . . ? C28 C29 H29 115.1 . . ? C29 C30 C31 116.0(14) . . ? C29 C30 H30 122.0 . . ? C31 C30 H30 122.0 . . ? C30 C31 C32 119.7(14) . . ? C30 C31 N4 121.0(13) . . ? C32 C31 N4 119.2(13) . . ? C33 C32 C31 123.7(14) . . ? C33 C32 H32 118.2 . . ? C31 C32 H32 118.2 . . ? C32 C33 C28 117.5(14) . . ? C32 C33 H33 121.3 . . ? C28 C33 H33 121.3 . . ? O51A C241 O61A 127(2) . . ? O51A C241 C25A 111.1(17) . . ? O61A C241 C25A 118.4(16) . . ? C27A N3A C25A 116.8(14) . . ? C27A N3A H37A 121.8 . . ? C25A N3A H37A 121.3 . . ? O10A N4A O9A 131.0(14) . . ? O10A N4A C31A 114.4(13) . . ? O9A N4A C31A 114.4(13) . . ? O5A C24A O6A 121(2) . . ? O5A C24A C25A 117(2) . . ? O6A C24A C25A 122.6(19) . . ? C26A C25A N3A 103.5(15) . . ? C26A C25A C241 98.6(16) . . ? N3A C25A C241 105.1(16) . . ? C26A C25A C24A 134.4(19) . . ? N3A C25A C24A 112.1(16) . . ? C241 C25A C24A 45.9(13) . . ? C26A C25A H25A 102.1 . . ? N3A C25A H25A 104.8 . . ? C241 C25A H25A 138.1 . . ? C24A C25A H25A 95.5 . . ? O7A C26A C25A 110.5(15) . . ? O7A C26A H26C 104.6 . . ? C25A C26A H26C 119.1 . . ? O7A C26A H26D 101.2 . . ? C25A C26A H26D 117.0 . . ? H26C C26A H26D 102.3 . . ? O8A C27A N3A 126.3(17) . . ? O8A C27A C28A 119.3(16) . . ? N3A C27A C28A 112.9(15) . . ? C29A C28A C33A 129.0(17) . . ? C29A C28A C27A 120.9(16) . . ? C33A C28A C27A 109.9(15) . . ? C28A C29A C30A 117.6(16) . . ? C28A C29A H29A 121.2 . . ? C30A C29A H29A 121.2 . . ? C31A C30A C29A 119.8(15) . . ? C31A C30A H30A 120.1 . . ? C29A C30A H30A 120.1 . . ? C30A C31A C32A 122.4(13) . . ? C30A C31A N4A 115.5(13) . . ? C32A C31A N4A 122.0(13) . . ? C31A C32A C33A 115.2(14) . . ? C31A C32A H32A 122.4 . . ? C33A C32A H32A 122.4 . . ? C28A C33A C32A 115.8(15) . . ? C28A C33A H33A 122.1 . . ? C32A C33A H33A 122.1 . . ? C27B N3B C25B 121.2(10) . . ? C27B N3B H37B 119.4 . . ? C25B N3B H37B 119.4 . . ? O9B N4B O10B 121.8(10) . . ? O9B N4B C31B 119.9(11) . . ? O10B N4B C31B 118.1(11) . . ? O6B C24B O5B 127.2(11) . . ? O6B C24B C25B 116.1(11) . . ? O5B C24B C25B 116.7(11) . . ? N3B C25B C26B 115.1(9) . . ? N3B C25B C24B 112.2(9) . . ? C26B C25B C24B 107.9(10) . . ? N3B C25B H25B 107.1 . . ? C26B C25B H25B 107.1 . . ? C24B C25B H25B 107.1 . . ? O7B C26B C25B 109.5(9) . . ? O7B C26B H26E 109.8 . . ? C25B C26B H26E 109.8 . . ? O7B C26B H26F 109.8 . . ? C25B C26B H26F 109.8 . . ? H26E C26B H26F 108.2 . . ? O8B C27B N3B 125.0(11) . . ? O8B C27B C28B 116.0(11) . . ? N3B C27B C28B 118.9(11) . . ? C33B C28B C29B 117.5(11) . . ? C33B C28B C27B 119.8(11) . . ? C29B C28B C27B 122.3(11) . . ? C30B C29B C28B 121.7(12) . . ? C30B C29B H29B 119.2 . . ? C28B C29B H29B 119.2 . . ? C29B C30B C31B 116.4(12) . . ? C29B C30B H30B 121.8 . . ? C31B C30B H30B 121.8 . . ? C32B C31B C30B 123.2(12) . . ? C32B C31B N4B 116.5(11) . . ? C30B C31B N4B 120.1(11) . . ? C33B C32B C31B 117.6(12) . . ? C33B C32B H32B 121.2 . . ? C31B C32B H32B 121.2 . . ? C28B C33B C32B 123.2(12) . . ? C28B C33B H33B 118.4 . . ? C32B C33B H33B 118.4 . . ? O34 C34 C35 137(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 C22 O2 C2 C3 170.3(10) . . . . ? C22 O2 C2 C1 -12.9(16) . . . . ? C6 C1 C2 O2 -176.8(10) . . . . ? C6 C1 C2 C3 -0.1(17) . . . . ? O2 C2 C3 O3 -3.8(15) . . . . ? C1 C2 C3 O3 179.3(10) . . . . ? O2 C2 C3 C4 175.4(10) . . . . ? C1 C2 C3 C4 -1.5(17) . . . . ? C23 O3 C3 C2 179.3(10) . . . . ? C23 O3 C3 C4 0.1(16) . . . . ? C2 C3 C4 C5 2.5(17) . . . . ? O3 C3 C4 C5 -178.3(10) . . . . ? C3 C4 C5 C6 -1.9(17) . . . . ? C3 C4 C5 C7 179.4(11) . . . . ? C4 C5 C6 C1 0.4(18) . . . . ? C7 C5 C6 C1 179.3(10) . . . . ? C4 C5 C6 N1 176.4(11) . . . . ? C7 C5 C6 N1 -4.7(13) . . . . ? C2 C1 C6 C5 0.7(17) . . . . ? C2 C1 C6 N1 -174.7(11) . . . . ? C9 N1 C6 C5 -159.7(11) . . . . ? C8 N1 C6 C5 -5.7(13) . . . . ? C9 N1 C6 C1 16.1(18) . . . . ? C8 N1 C6 C1 170.1(11) . . . . ? C4 C5 C7 C8 -168.6(13) . . . . ? C6 C5 C7 C8 12.6(12) . . . . ? C4 C5 C7 C21 -40.0(18) . . . . ? C6 C5 C7 C21 141.2(10) . . . . ? C4 C5 C7 C17 72.9(16) . . . . ? C6 C5 C7 C17 -105.9(11) . . . . ? C9 N1 C8 C7 169.0(10) . . . . ? C6 N1 C8 C7 13.7(12) . . . . ? C9 N1 C8 C18 45.7(13) . . . . ? C6 N1 C8 C18 -109.6(10) . . . . ? C5 C7 C8 N1 -15.5(11) . . . . ? C21 C7 C8 N1 -141.7(10) . . . . ? C17 C7 C8 N1 101.5(11) . . . . ? C5 C7 C8 C18 101.5(11) . . . . ? C21 C7 C8 C18 -24.7(15) . . . . ? C17 C7 C8 C18 -141.4(10) . . . . ? C6 N1 C9 O4 -27.5(18) . . . . ? C8 N1 C9 O4 -178.6(10) . . . . ? C6 N1 C9 C10 151.5(11) . . . . ? C8 N1 C9 C10 0.4(16) . . . . ? O4 C9 C10 C11 155.3(11) . . . . ? N1 C9 C10 C11 -23.7(16) . . . . ? C12 O1 C11 C18 -72.8(11) . . . . ? C12 O1 C11 C10 168.2(8) . . . . ? C9 C10 C11 O1 117.3(11) . . . . ? C9 C10 C11 C18 -2.5(14) . . . . ? C11 O1 C12 C13 88.9(11) . . . . ? O1 C12 C13 C14 -63.8(15) . . . . ? C12 C13 C14 C19 -1.3(18) . . . . ? C12 C13 C14 C15 177.7(10) . . . . ? C21 N2 C15 C14 -48.5(12) . . . . ? C16 N2 C15 C14 77.5(11) . . . . ? C13 C14 C15 N2 -124.0(12) . . . . ? C19 C14 C15 N2 55.0(12) . . . . ? C15 N2 C16 C17 -142.0(9) . . . . ? C21 N2 C16 C17 -13.0(12) . . . . ? N2 C16 C17 C7 34.9(11) . . . . ? C8 C7 C17 C16 82.6(11) . . . . ? C5 C7 C17 C16 -164.4(9) . . . . ? C21 C7 C17 C16 -43.6(11) . . . . ? N1 C8 C18 C19 157.7(9) . . . . ? C7 C8 C18 C19 40.5(14) . . . . ? N1 C8 C18 C11 -69.9(11) . . . . ? C7 C8 C18 C11 172.9(9) . . . . ? O1 C11 C18 C19 61.7(13) . . . . ? C10 C11 C18 C19 178.2(9) . . . . ? O1 C11 C18 C8 -68.6(11) . . . . ? C10 C11 C18 C8 47.9(12) . . . . ? C13 C14 C19 C18 57.6(15) . . . . ? C15 C14 C19 C18 -121.4(11) . . . . ? C13 C14 C19 C20 175.1(10) . . . . ? C15 C14 C19 C20 -3.9(13) . . . . ? C8 C18 C19 C14 57.6(13) . . . . ? C11 C18 C19 C14 -70.3(13) . . . . ? C8 C18 C19 C20 -61.1(12) . . . . ? C11 C18 C19 C20 171.1(10) . . . . ? C14 C19 C20 C21 -53.7(12) . . . . ? C18 C19 C20 C21 68.7(11) . . . . ? C19 C20 C21 N2 60.4(11) . . . . ? C19 C20 C21 C7 -53.9(13) . . . . ? C15 N2 C21 C20 -6.4(12) . . . . ? C16 N2 C21 C20 -134.7(9) . . . . ? C15 N2 C21 C7 113.8(10) . . . . ? C16 N2 C21 C7 -14.5(11) . . . . ? C8 C7 C21 C20 31.8(14) . . . . ? C5 C7 C21 C20 -88.8(12) . . . . ? C17 C7 C21 C20 153.7(9) . . . . ? C8 C7 C21 N2 -86.9(12) . . . . ? C5 C7 C21 N2 152.5(9) . . . . ? C17 C7 C21 N2 35.0(11) . . . . ? C22A O2A C2A C1A -0.9(17) . . . . ? C22A O2A C2A C3A -178.2(10) . . . . ? C6A C1A C2A O2A 179.8(11) . . . . ? C6A C1A C2A C3A -3.1(18) . . . . ? C23A O3A C3A C4A 5.2(16) . . . . ? C23A O3A C3A C2A -177.3(10) . . . . ? O2A C2A C3A O3A -2.1(15) . . . . ? C1A C2A C3A O3A -179.6(11) . . . . ? O2A C2A C3A C4A 175.5(10) . . . . ? C1A C2A C3A C4A -1.9(18) . . . . ? O3A C3A C4A C5A 179.3(11) . . . . ? C2A C3A C4A C5A 1.9(17) . . . . ? C3A C4A C5A C6A 3.1(18) . . . . ? C3A C4A C5A C7A -169.9(12) . . . . ? C2A C1A C6A C5A 8.5(18) . . . . ? C2A C1A C6A N1A -178.2(11) . . . . ? C4A C5A C6A C1A -8.7(19) . . . . ? C7A C5A C6A C1A 165.6(11) . . . . ? C4A C5A C6A N1A 176.9(11) . . . . ? C7A C5A C6A N1A -8.8(14) . . . . ? C9A N1A C6A C1A 29.3(18) . . . . ? C8A N1A C6A C1A -178.9(11) . . . . ? C9A N1A C6A C5A -156.6(11) . . . . ? C8A N1A C6A C5A -4.9(13) . . . . ? C4A C5A C7A C17A 71.6(17) . . . . ? C6A C5A C7A C17A -102.0(12) . . . . ? C4A C5A C7A C21A -44.5(18) . . . . ? C6A C5A C7A C21A 142.0(11) . . . . ? C4A C5A C7A C8A -168.3(13) . . . . ? C6A C5A C7A C8A 18.1(13) . . . . ? C9A N1A C8A C18A 44.0(13) . . . . ? C6A N1A C8A C18A -108.4(10) . . . . ? C9A N1A C8A C7A 168.0(10) . . . . ? C6A N1A C8A C7A 15.6(12) . . . . ? C5A C7A C8A N1A -19.9(12) . . . . ? C17A C7A C8A N1A 102.2(10) . . . . ? C21A C7A C8A N1A -144.2(9) . . . . ? C5A C7A C8A C18A 96.4(12) . . . . ? C17A C7A C8A C18A -141.5(10) . . . . ? C21A C7A C8A C18A -27.9(14) . . . . ? C6A N1A C9A O4A -21.4(17) . . . . ? C8A N1A C9A O4A -169.9(10) . . . . ? C6A N1A C9A C10A 158.5(10) . . . . ? C8A N1A C9A C10A 10.0(15) . . . . ? O4A C9A C10A C11A 139.1(11) . . . . ? N1A C9A C10A C11A -40.8(15) . . . . ? C12A O1A C11A C10A 175.5(9) . . . . ? C12A O1A C11A C18A -67.9(13) . . . . ? C9A C10A C11A O1A 131.4(11) . . . . ? C9A C10A C11A C18A 12.9(15) . . . . ? C11A O1A C12A C13A 87.1(13) . . . . ? O1A C12A C13A C14A -60.5(16) . . . . ? C12A C13A C14A C15A 175.3(10) . . . . ? C12A C13A C14A C19A -4.1(19) . . . . ? C16A N2A C15A C14A 74.1(12) . . . . ? C21A N2A C15A C14A -47.7(12) . . . . ? C13A C14A C15A N2A -126.5(12) . . . . ? C19A C14A C15A N2A 52.9(13) . . . . ? C15A N2A C16A C17A -142.0(10) . . . . ? C21A N2A C16A C17A -15.9(12) . . . . ? C5A C7A C17A C16A -165.7(10) . . . . ? C21A C7A C17A C16A -42.8(11) . . . . ? C8A C7A C17A C16A 77.8(12) . . . . ? N2A C16A C17A C7A 37.1(12) . . . . ? N1A C8A C18A C19A 157.5(9) . . . . ? C7A C8A C18A C19A 42.3(14) . . . . ? N1A C8A C18A C11A -69.4(11) . . . . ? C7A C8A C18A C11A 175.5(10) . . . . ? O1A C11A C18A C19A 57.3(14) . . . . ? C10A C11A C18A C19A 170.9(10) . . . . ? O1A C11A C18A C8A -72.7(11) . . . . ? C10A C11A C18A C8A 40.9(13) . . . . ? C8A C18A C19A C20A -62.5(13) . . . . ? C11A C18A C19A C20A 169.6(11) . . . . ? C8A C18A C19A C14A 59.5(14) . . . . ? C11A C18A C19A C14A -68.4(15) . . . . ? C13A C14A C19A C20A -178.5(11) . . . . ? C15A C14A C19A C20A 2.1(14) . . . . ? C13A C14A C19A C18A 59.3(16) . . . . ? C15A C14A C19A C18A -120.1(11) . . . . ? C18A C19A C20A C21A 67.0(12) . . . . ? C14A C19A C20A C21A -58.9(12) . . . . ? C15A N2A C21A C7A 116.2(10) . . . . ? C16A N2A C21A C7A -10.6(12) . . . . ? C15A N2A C21A C20A -7.4(12) . . . . ? C16A N2A C21A C20A -134.2(10) . . . . ? C5A C7A C21A N2A 155.5(10) . . . . ? C17A C7A C21A N2A 32.9(11) . . . . ? C8A C7A C21A N2A -85.7(11) . . . . ? C5A C7A C21A C20A -85.3(13) . . . . ? C17A C7A C21A C20A 152.2(10) . . . . ? C8A C7A C21A C20A 33.6(14) . . . . ? C19A C20A C21A N2A 63.3(12) . . . . ? C19A C20A C21A C7A -53.9(13) . . . . ? C22B O2B C2B C1B -0.4(16) . . . . ? C22B O2B C2B C3B -175.6(9) . . . . ? C6B C1B C2B O2B 179.5(11) . . . . ? C6B C1B C2B C3B -5.5(17) . . . . ? C23B O3B C3B C2B -178.1(10) . . . . ? C23B O3B C3B C4B 1.6(16) . . . . ? O2B C2B C3B O3B -3.3(15) . . . . ? C1B C2B C3B O3B -178.9(10) . . . . ? O2B C2B C3B C4B 177.1(10) . . . . ? C1B C2B C3B C4B 1.5(18) . . . . ? O3B C3B C4B C5B -179.5(10) . . . . ? C2B C3B C4B C5B 0.2(16) . . . . ? C3B C4B C5B C6B 2.2(16) . . . . ? C3B C4B C5B C7B -174.0(11) . . . . ? C2B C1B C6B C5B 8.0(18) . . . . ? C2B C1B C6B N1B -176.3(11) . . . . ? C4B C5B C6B C1B -6.4(18) . . . . ? C7B C5B C6B C1B 170.3(10) . . . . ? C4B C5B C6B N1B 177.1(10) . . . . ? C7B C5B C6B N1B -6.1(13) . . . . ? C9B N1B C6B C1B 30.0(19) . . . . ? C8B N1B C6B C1B 175.6(11) . . . . ? C9B N1B C6B C5B -153.9(11) . . . . ? C8B N1B C6B C5B -8.4(12) . . . . ? C4B C5B C7B C21B -40.9(16) . . . . ? C6B C5B C7B C21B 142.6(10) . . . . ? C4B C5B C7B C8B -166.3(12) . . . . ? C6B C5B C7B C8B 17.2(12) . . . . ? C4B C5B C7B C17B 74.3(15) . . . . ? C6B C5B C7B C17B -102.2(11) . . . . ? C9B N1B C8B C18B 43.1(13) . . . . ? C6B N1B C8B C18B -104.1(10) . . . . ? C9B N1B C8B C7B 165.6(10) . . . . ? C6B N1B C8B C7B 18.4(11) . . . . ? C5B C7B C8B N1B -20.9(11) . . . . ? C21B C7B C8B N1B -146.6(9) . . . . ? C17B C7B C8B N1B 100.8(9) . . . . ? C5B C7B C8B C18B 95.8(11) . . . . ? C21B C7B C8B C18B -29.9(13) . . . . ? C17B C7B C8B C18B -142.5(9) . . . . ? C6B N1B C9B O4B -27.4(18) . . . . ? C8B N1B C9B O4B -169.8(10) . . . . ? C6B N1B C9B C10B 158.9(10) . . . . ? C8B N1B C9B C10B 16.5(14) . . . . ? O4B C9B C10B C11B 138.0(10) . . . . ? N1B C9B C10B C11B -47.8(14) . . . . ? C12B O1B C11B C18B -63.4(11) . . . . ? C12B O1B C11B C10B 173.6(8) . . . . ? C9B C10B C11B O1B 140.7(9) . . . . ? C9B C10B C11B C18B 16.3(14) . . . . ? C11B O1B C12B C13B 91.9(10) . . . . ? O1B C12B C13B C14B -71.3(13) . . . . ? C12B C13B C14B C19B 0.9(17) . . . . ? C12B C13B C14B C15B 178.9(9) . . . . ? C16B N2B C15B C14B 83.2(11) . . . . ? C21B N2B C15B C14B -43.7(12) . . . . ? C13B C14B C15B N2B -130.6(11) . . . . ? C19B C14B C15B N2B 47.6(12) . . . . ? C15B N2B C16B C17B -142.9(8) . . . . ? C21B N2B C16B C17B -12.3(11) . . . . ? N2B C16B C17B C7B 33.5(11) . . . . ? C5B C7B C17B C16B -165.2(9) . . . . ? C21B C7B C17B C16B -41.7(10) . . . . ? C8B C7B C17B C16B 79.5(10) . . . . ? N1B C8B C18B C19B 158.6(8) . . . . ? C7B C8B C18B C19B 43.9(13) . . . . ? N1B C8B C18B C11B -69.7(10) . . . . ? C7B C8B C18B C11B 175.7(9) . . . . ? O1B C11B C18B C19B 49.4(14) . . . . ? C10B C11B C18B C19B 166.0(9) . . . . ? O1B C11B C18B C8B -78.2(11) . . . . ? C10B C11B C18B C8B 38.5(12) . . . . ? C13B C14B C19B C20B 179.8(10) . . . . ? C15B C14B C19B C20B 1.7(13) . . . . ? C13B C14B C19B C18B 59.8(14) . . . . ? C15B C14B C19B C18B -118.4(10) . . . . ? C8B C18B C19B C20B -61.9(11) . . . . ? C11B C18B C19B C20B 174.0(9) . . . . ? C8B C18B C19B C14B 60.7(12) . . . . ? C11B C18B C19B C14B -63.4(13) . . . . ? C14B C19B C20B C21B -56.9(11) . . . . ? C18B C19B C20B C21B 68.2(11) . . . . ? C16B N2B C21B C20B -137.7(9) . . . . ? C15B N2B C21B C20B -9.1(12) . . . . ? C16B N2B C21B C7B -14.7(11) . . . . ? C15B N2B C21B C7B 113.8(9) . . . . ? C19B C20B C21B N2B 60.9(11) . . . . ? C19B C20B C21B C7B -56.6(12) . . . . ? C5B C7B C21B N2B 156.9(9) . . . . ? C8B C7B C21B N2B -83.8(11) . . . . ? C17B C7B C21B N2B 34.4(10) . . . . ? C5B C7B C21B C20B -83.3(12) . . . . ? C8B C7B C21B C20B 36.1(13) . . . . ? C17B C7B C21B C20B 154.2(9) . . . . ? C27 N3 C25 C26 81.9(19) . . . . ? C27 N3 C25 C24 -151.9(13) . . . . ? O6 C24 C25 N3 6(2) . . . . ? O5 C24 C25 N3 -178.1(13) . . . . ? O6 C24 C25 C26 131.4(15) . . . . ? O5 C24 C25 C26 -52.4(18) . . . . ? N3 C25 C26 O7 58.7(17) . . . . ? C24 C25 C26 O7 -66.6(17) . . . . ? C25 N3 C27 O8 -7(2) . . . . ? C25 N3 C27 C28 177.6(13) . . . . ? O8 C27 C28 C29 13(2) . . . . ? N3 C27 C28 C29 -171.6(13) . . . . ? O8 C27 C28 C33 -164.9(14) . . . . ? N3 C27 C28 C33 10(2) . . . . ? C33 C28 C29 C30 3(2) . . . . ? C27 C28 C29 C30 -175.0(13) . . . . ? C28 C29 C30 C31 -6(2) . . . . ? C29 C30 C31 C32 2.0(19) . . . . ? C29 C30 C31 N4 -175.4(11) . . . . ? O10 N4 C31 C30 167.4(12) . . . . ? O9 N4 C31 C30 -15.0(19) . . . . ? O10 N4 C31 C32 -10.0(19) . . . . ? O9 N4 C31 C32 167.5(12) . . . . ? C30 C31 C32 C33 3(2) . . . . ? N4 C31 C32 C33 -179.2(12) . . . . ? C31 C32 C33 C28 -5(2) . . . . ? C29 C28 C33 C32 2.3(18) . . . . ? C27 C28 C33 C32 -179.4(13) . . . . ? C27A N3A C25A C26A 149.9(15) . . . . ? C27A N3A C25A C241 -107.1(18) . . . . ? C27A N3A C25A C24A -59(2) . . . . ? O51A C241 C25A C26A 163(2) . . . . ? O61A C241 C25A C26A -37(3) . . . . ? O51A C241 C25A N3A 56(3) . . . . ? O61A C241 C25A N3A -144(2) . . . . ? O51A C241 C25A C24A -50(2) . . . . ? O61A C241 C25A C24A 110(3) . . . . ? O5A C24A C25A C26A 110(3) . . . . ? O6A C24A C25A C26A -67(4) . . . . ? O5A C24A C25A N3A -28(3) . . . . ? O6A C24A C25A N3A 155(3) . . . . ? O5A C24A C25A C241 61(3) . . . . ? O6A C24A C25A C241 -115(4) . . . . ? N3A C25A C26A O7A -69.8(18) . . . . ? C241 C25A C26A O7A -177.7(15) . . . . ? C24A C25A C26A O7A 149(2) . . . . ? C25A N3A C27A O8A -12(3) . . . . ? C25A N3A C27A C28A -178.0(13) . . . . ? O8A C27A C28A C29A -142.5(18) . . . . ? N3A C27A C28A C29A 24(2) . . . . ? O8A C27A C28A C33A 42(2) . . . . ? N3A C27A C28A C33A -151.3(14) . . . . ? C33A C28A C29A C30A -2(2) . . . . ? C27A C28A C29A C30A -177.1(13) . . . . ? C28A C29A C30A C31A 5(2) . . . . ? C29A C30A C31A C32A -2(2) . . . . ? C29A C30A C31A N4A 174.9(11) . . . . ? O10A N4A C31A C30A -162.4(12) . . . . ? O9A N4A C31A C30A 22.1(16) . . . . ? O10A N4A C31A C32A 14.8(17) . . . . ? O9A N4A C31A C32A -160.7(13) . . . . ? C30A C31A C32A C33A -2(2) . . . . ? N4A C31A C32A C33A -179.0(11) . . . . ? C29A C28A C33A C32A -2(2) . . . . ? C27A C28A C33A C32A 173.1(12) . . . . ? C31A C32A C33A C28A 4(2) . . . . ? C27B N3B C25B C26B 139.9(11) . . . . ? C27B N3B C25B C24B -96.3(12) . . . . ? O6B C24B C25B N3B 177.2(11) . . . . ? O5B C24B C25B N3B -4.6(16) . . . . ? O6B C24B C25B C26B -55.0(14) . . . . ? O5B C24B C25B C26B 123.2(12) . . . . ? N3B C25B C26B O7B -59.1(13) . . . . ? C24B C25B C26B O7B 174.8(10) . . . . ? C25B N3B C27B O8B 1.3(17) . . . . ? C25B N3B C27B C28B 177.2(9) . . . . ? O8B C27B C28B C33B -18.3(15) . . . . ? N3B C27B C28B C33B 165.4(10) . . . . ? O8B C27B C28B C29B 169.0(10) . . . . ? N3B C27B C28B C29B -7.2(16) . . . . ? C33B C28B C29B C30B 5.0(16) . . . . ? C27B C28B C29B C30B 177.8(10) . . . . ? C28B C29B C30B C31B -6.8(17) . . . . ? C29B C30B C31B C32B 6.4(18) . . . . ? C29B C30B C31B N4B -179.6(10) . . . . ? O9B N4B C31B C32B -16.0(16) . . . . ? O10B N4B C31B C32B 168.6(10) . . . . ? O9B N4B C31B C30B 169.6(11) . . . . ? O10B N4B C31B C30B -5.8(17) . . . . ? C30B C31B C32B C33B -4.1(18) . . . . ? N4B C31B C32B C33B -178.3(10) . . . . ? C29B C28B C33B C32B -2.4(16) . . . . ? C27B C28B C33B C32B -175.4(10) . . . . ? C31B C32B C33B C28B 2.0(17) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.557 _refine_diff_density_min -0.308 _refine_diff_density_rms 0.073 # start Validation Reply Form _vrf_PLAT213_10 ; PROBLEM: Atom C22A has ADP max/min Ratio ..... 5.60 oblat RESPONSE: unsufficient quality of the intermediate crystal, poor crystal data and small ratio of reflections to parameters ; _vrf_PLAT220_10 ; PROBLEM: Large Non-Solvent O Ueq(max)/Ueq(min) ... 8.36 Ratio RESPONSE: probably disordered ; _vrf_PLAT306_10 ; PROBLEM: Isolated Oxygen Atom (H-atoms Missing ?) ....... O13 RESPONSE: H atoms for water molecules are missing. ; _vrf_PLAT430_10 ; PROBLEM: Short Inter D...A Contact O15 .. O12 .. 2.43 Ang. RESPONSE: disordered water molecules - H atoms are missing ; # end Validation Reply Form #===== end data_11 _database_code_depnum_ccdc_archive 'CCDC 758152' #TrackingRef 'bialonska2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; brucinium N-(4-nitrobenzoyl)-L-serinate ethanol solvate ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C23 H27 N2 O4, C10 H9 N2 O6, C2 H6 O' _chemical_formula_sum 'C35 H42 N4 O11' _chemical_formula_weight 694.73 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 9.332(2) _cell_length_b 12.953(3) _cell_length_c 26.793(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3238.7(12) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 10293 _cell_measurement_theta_min 3.09 _cell_measurement_theta_max 35.25 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.40 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.425 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1472 _exptl_absorpt_coefficient_mu 0.107 _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 78852 _diffrn_reflns_av_R_equivalents 0.0505 _diffrn_reflns_av_sigmaI/netI 0.0251 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -42 _diffrn_reflns_limit_l_max 38 _diffrn_reflns_theta_min 3.09 _diffrn_reflns_theta_max 34.00 _reflns_number_total 7238 _reflns_number_gt 6691 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET) (compiled May 8 2007,13:10:02) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET) (compiled May 8 2007,13:10:02) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET) (compiled May 8 2007,13:10:02) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0641P)^2^+0.3043P] 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 7238 _refine_ls_number_parameters 451 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0476 _refine_ls_R_factor_gt 0.0416 _refine_ls_wR_factor_ref 0.1038 _refine_ls_wR_factor_gt 0.1014 _refine_ls_goodness_of_fit_ref 1.063 _refine_ls_restrained_S_all 1.063 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.41802(14) 0.70057(10) 0.65540(5) 0.0268(3) Uani 1 1 d . . . O2 O 0.82064(11) 0.10869(8) 0.72470(4) 0.0180(2) Uani 1 1 d . . . O3 O 0.59850(13) 0.01613(8) 0.68971(5) 0.0194(2) Uani 1 1 d . . . O4 O 0.79874(12) 0.49657(9) 0.71365(5) 0.0248(3) Uani 1 1 d . . . N1 N 0.56782(12) 0.44243(9) 0.70374(4) 0.0119(2) Uani 1 1 d . . . N2 N 0.10838(13) 0.39116(9) 0.64574(5) 0.0132(2) Uani 1 1 d . . . H24 H 0.0388 0.3411 0.6403 0.016 Uiso 1 1 calc R . . C1 C 0.71117(14) 0.27895(11) 0.71835(5) 0.0130(2) Uani 1 1 d . . . H1 H 0.7932 0.3133 0.7312 0.016 Uiso 1 1 calc R . . C2 C 0.70855(14) 0.17197(11) 0.71302(5) 0.0131(2) Uani 1 1 d . . . C3 C 0.58577(15) 0.12097(10) 0.69439(5) 0.0131(2) Uani 1 1 d . . . C4 C 0.46432(15) 0.17733(10) 0.68164(5) 0.0127(2) Uani 1 1 d . . . H4 H 0.3807 0.1434 0.6698 0.015 Uiso 1 1 calc R . . C5 C 0.46712(14) 0.28433(10) 0.68648(5) 0.0110(2) Uani 1 1 d . . . C6 C 0.58921(14) 0.33399(10) 0.70409(5) 0.0112(2) Uani 1 1 d . . . C7 C 0.34714(14) 0.36083(10) 0.67925(5) 0.0103(2) Uani 1 1 d . . . C8 C 0.42700(14) 0.46630(10) 0.68051(5) 0.0107(2) Uani 1 1 d . . . H8 H 0.3731 0.5161 0.7020 0.013 Uiso 1 1 calc R . . C9 C 0.67402(15) 0.51496(11) 0.70147(6) 0.0153(2) Uani 1 1 d . . . C10 C 0.62625(17) 0.62107(11) 0.68444(6) 0.0179(3) Uani 1 1 d . . . H10A H 0.7126 0.6614 0.6754 0.022 Uiso 1 1 calc R . . H10B H 0.5803 0.6563 0.7131 0.022 Uiso 1 1 calc R . . C11 C 0.52171(17) 0.62418(12) 0.63994(6) 0.0185(3) Uani 1 1 d . . . H11 H 0.5733 0.6492 0.6095 0.022 Uiso 1 1 calc R . . C12 C 0.3116(2) 0.72661(14) 0.61900(9) 0.0321(4) Uani 1 1 d . . . H12A H 0.3541 0.7223 0.5852 0.039 Uiso 1 1 calc R . . H12B H 0.2793 0.7985 0.6245 0.039 Uiso 1 1 calc R . . C13 C 0.18551(18) 0.65516(13) 0.62225(7) 0.0245(3) Uani 1 1 d . . . H13 H 0.0955 0.6818 0.6327 0.029 Uiso 1 1 calc R . . C14 C 0.19630(16) 0.55550(12) 0.61093(6) 0.0162(2) Uani 1 1 d . . . C15 C 0.06959(15) 0.48469(12) 0.61495(6) 0.0166(3) Uani 1 1 d . . . H15A H 0.0392 0.4627 0.5812 0.020 Uiso 1 1 calc R . . H15B H -0.0114 0.5216 0.6308 0.020 Uiso 1 1 calc R . . C16 C 0.10992(15) 0.41528(12) 0.70084(5) 0.0147(2) Uani 1 1 d . . . H16A H 0.0190 0.3936 0.7168 0.018 Uiso 1 1 calc R . . H16B H 0.1238 0.4901 0.7065 0.018 Uiso 1 1 calc R . . C17 C 0.23516(14) 0.35404(11) 0.72147(5) 0.0131(2) Uani 1 1 d . . . H17A H 0.2076 0.2815 0.7281 0.016 Uiso 1 1 calc R . . H17B H 0.2719 0.3853 0.7527 0.016 Uiso 1 1 calc R . . C18 C 0.45994(15) 0.51610(11) 0.62993(5) 0.0133(2) Uani 1 1 d . . . H18 H 0.5404 0.4750 0.6154 0.016 Uiso 1 1 calc R . . C19 C 0.33535(16) 0.50641(11) 0.59274(5) 0.0148(2) Uani 1 1 d . . . H19 H 0.3638 0.5391 0.5604 0.018 Uiso 1 1 calc R . . C20 C 0.31103(17) 0.39047(12) 0.58435(5) 0.0159(2) Uani 1 1 d . . . H20A H 0.2412 0.3798 0.5570 0.019 Uiso 1 1 calc R . . H20B H 0.4023 0.3567 0.5749 0.019 Uiso 1 1 calc R . . C21 C 0.25418(14) 0.34415(11) 0.63241(5) 0.0125(2) Uani 1 1 d . . . H21 H 0.2413 0.2682 0.6273 0.015 Uiso 1 1 calc R . . C22 C 0.95420(16) 0.15759(12) 0.73538(6) 0.0184(3) Uani 1 1 d . . . H22A H 1.0263 0.1050 0.7432 0.028 Uiso 1 1 calc R . . H22B H 0.9427 0.2039 0.7640 0.028 Uiso 1 1 calc R . . H22C H 0.9853 0.1975 0.7063 0.028 Uiso 1 1 calc R . . C23 C 0.4789(2) -0.03757(12) 0.66885(7) 0.0239(3) Uani 1 1 d . . . H23A H 0.5003 -0.1116 0.6674 0.036 Uiso 1 1 calc R . . H23B H 0.4603 -0.0117 0.6351 0.036 Uiso 1 1 calc R . . H23C H 0.3942 -0.0262 0.6898 0.036 Uiso 1 1 calc R . . O5 O -0.07665(12) 0.25027(9) 0.61630(4) 0.0171(2) Uani 1 1 d . . . O6 O -0.03851(13) 0.28437(9) 0.53551(4) 0.0196(2) Uani 1 1 d . . . O7 O -0.49588(12) 0.15975(10) 0.56279(4) 0.0213(2) Uani 1 1 d . . . H7 H -0.5251 0.1758 0.5342 0.032 Uiso 1 1 calc R . . O8 O -0.25241(13) 0.48207(9) 0.55351(4) 0.0186(2) Uani 1 1 d . . . O9 O -0.6345(2) 0.69963(13) 0.35524(7) 0.0461(4) Uani 1 1 d . . . O10 O -0.4998(2) 0.60616(13) 0.30770(5) 0.0423(4) Uani 1 1 d . . . N3 N -0.32841(14) 0.32883(9) 0.52236(5) 0.0149(2) Uani 1 1 d . . . H3 H -0.3681 0.2959 0.4972 0.018 Uiso 1 1 calc R . . N4 N -0.54555(19) 0.63156(12) 0.34861(6) 0.0287(3) Uani 1 1 d . . . C24 C -0.11840(15) 0.26912(11) 0.57245(5) 0.0133(2) Uani 1 1 d . . . C25 C -0.28292(15) 0.27141(11) 0.56617(5) 0.0129(2) Uani 1 1 d . . . H25 H -0.3247 0.3058 0.5962 0.015 Uiso 1 1 calc R . . C26 C -0.34332(16) 0.16131(12) 0.56352(5) 0.0164(3) Uani 1 1 d . . . H26A H -0.3067 0.1271 0.5330 0.020 Uiso 1 1 calc R . . H26B H -0.3089 0.1216 0.5927 0.020 Uiso 1 1 calc R . . C27 C -0.31066(15) 0.43121(11) 0.51982(5) 0.0141(2) Uani 1 1 d . . . C28 C -0.36969(16) 0.48252(11) 0.47412(5) 0.0145(2) Uani 1 1 d . . . C29 C -0.42352(17) 0.58290(12) 0.47861(6) 0.0182(3) Uani 1 1 d . . . H29 H -0.4179 0.6177 0.5098 0.022 Uiso 1 1 calc R . . C30 C -0.48517(18) 0.63207(12) 0.43784(6) 0.0200(3) Uani 1 1 d . . . H30 H -0.5254 0.6992 0.4408 0.024 Uiso 1 1 calc R . . C31 C -0.48589(18) 0.57975(12) 0.39269(6) 0.0201(3) Uani 1 1 d . . . C32 C -0.4299(2) 0.48166(13) 0.38653(6) 0.0273(4) Uani 1 1 d . . . H32 H -0.4303 0.4488 0.3548 0.033 Uiso 1 1 calc R . . C33 C -0.3729(2) 0.43260(12) 0.42825(6) 0.0231(3) Uani 1 1 d . . . H33 H -0.3359 0.3645 0.4253 0.028 Uiso 1 1 calc R . . O34 O -0.07490(16) 0.64484(11) 0.51901(6) 0.0334(3) Uani 1 1 d . . . H34 H -0.1356 0.6079 0.5337 0.050 Uiso 1 1 calc R . . C34 C 0.0014(3) 0.58403(17) 0.48400(8) 0.0353(4) Uani 1 1 d . . . H34A H -0.0618 0.5673 0.4554 0.042 Uiso 1 1 calc R . . H34B H 0.0311 0.5184 0.4999 0.042 Uiso 1 1 calc R . . C35 C 0.1306(2) 0.64016(18) 0.46567(10) 0.0391(5) Uani 1 1 d . . . H35A H 0.1819 0.5969 0.4416 0.059 Uiso 1 1 calc R . . H35B H 0.1938 0.6558 0.4939 0.059 Uiso 1 1 calc R . . H35C H 0.1011 0.7046 0.4495 0.059 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0203(5) 0.0165(5) 0.0437(7) -0.0017(5) -0.0079(5) 0.0024(4) O2 0.0119(4) 0.0129(4) 0.0291(6) 0.0052(4) -0.0050(4) 0.0006(4) O3 0.0205(5) 0.0101(4) 0.0276(5) 0.0000(4) -0.0080(4) -0.0003(4) O4 0.0114(5) 0.0180(5) 0.0449(7) 0.0033(5) -0.0082(5) -0.0024(4) N1 0.0084(4) 0.0107(5) 0.0167(5) 0.0006(4) -0.0019(4) -0.0003(4) N2 0.0094(5) 0.0144(5) 0.0158(5) -0.0006(4) -0.0032(4) 0.0005(4) C1 0.0092(5) 0.0128(5) 0.0169(6) 0.0014(4) -0.0025(4) -0.0003(4) C2 0.0105(5) 0.0131(5) 0.0157(6) 0.0033(4) -0.0016(4) 0.0008(4) C3 0.0136(6) 0.0100(5) 0.0159(6) 0.0013(4) -0.0021(5) -0.0009(4) C4 0.0122(5) 0.0119(5) 0.0141(5) 0.0004(4) -0.0024(4) -0.0011(4) C5 0.0087(5) 0.0114(5) 0.0129(5) 0.0011(4) -0.0008(4) -0.0002(4) C6 0.0096(5) 0.0113(5) 0.0128(5) 0.0005(4) -0.0011(4) -0.0008(4) C7 0.0078(5) 0.0118(5) 0.0111(5) 0.0001(4) -0.0009(4) -0.0007(4) C8 0.0078(5) 0.0117(5) 0.0126(5) -0.0004(4) -0.0003(4) -0.0001(4) C9 0.0115(5) 0.0130(6) 0.0215(6) 0.0003(5) -0.0017(5) -0.0021(5) C10 0.0161(6) 0.0115(6) 0.0263(7) 0.0011(5) -0.0023(5) -0.0021(5) C11 0.0159(6) 0.0156(6) 0.0240(7) 0.0061(5) -0.0018(5) -0.0044(5) C12 0.0233(8) 0.0155(7) 0.0575(12) 0.0074(7) -0.0101(8) 0.0001(6) C13 0.0174(7) 0.0171(7) 0.0391(9) 0.0002(6) -0.0026(6) 0.0015(6) C14 0.0138(6) 0.0162(6) 0.0186(6) 0.0031(5) -0.0029(5) 0.0008(5) C15 0.0123(6) 0.0163(6) 0.0214(6) 0.0026(5) -0.0054(5) 0.0015(5) C16 0.0097(5) 0.0194(6) 0.0151(6) -0.0017(5) 0.0008(4) -0.0007(5) C17 0.0085(5) 0.0165(6) 0.0143(5) 0.0010(4) 0.0001(4) -0.0012(4) C18 0.0109(5) 0.0151(6) 0.0139(5) 0.0026(4) 0.0003(4) -0.0012(5) C19 0.0156(6) 0.0161(6) 0.0127(5) 0.0034(4) -0.0006(5) 0.0007(5) C20 0.0184(6) 0.0183(6) 0.0111(5) -0.0014(4) -0.0014(5) 0.0015(5) C21 0.0105(5) 0.0144(6) 0.0126(5) -0.0020(4) -0.0025(4) 0.0004(4) C22 0.0115(5) 0.0176(6) 0.0262(7) 0.0043(5) -0.0053(5) 0.0006(5) C23 0.0287(8) 0.0142(6) 0.0288(8) -0.0018(5) -0.0115(7) -0.0029(6) O5 0.0165(5) 0.0201(5) 0.0148(4) 0.0017(4) -0.0041(4) -0.0031(4) O6 0.0171(5) 0.0245(5) 0.0171(5) 0.0025(4) 0.0051(4) 0.0030(4) O7 0.0168(5) 0.0291(6) 0.0181(5) 0.0027(4) -0.0019(4) -0.0079(4) O8 0.0215(5) 0.0188(5) 0.0156(5) -0.0024(4) -0.0013(4) -0.0029(4) O9 0.0493(9) 0.0388(8) 0.0503(9) 0.0143(7) -0.0175(8) 0.0132(8) O10 0.0668(12) 0.0380(8) 0.0221(6) 0.0088(6) -0.0127(7) -0.0028(8) N3 0.0168(5) 0.0138(5) 0.0140(5) 0.0013(4) -0.0042(4) -0.0015(4) N4 0.0353(8) 0.0219(7) 0.0288(7) 0.0103(5) -0.0135(6) -0.0066(6) C24 0.0130(5) 0.0125(5) 0.0144(6) -0.0005(4) 0.0009(4) 0.0000(5) C25 0.0128(5) 0.0142(5) 0.0117(5) 0.0006(4) -0.0008(4) -0.0007(5) C26 0.0181(6) 0.0161(6) 0.0151(6) 0.0023(5) -0.0017(5) -0.0038(5) C27 0.0139(6) 0.0145(6) 0.0139(5) 0.0002(4) 0.0004(5) -0.0002(5) C28 0.0155(6) 0.0145(6) 0.0134(5) 0.0006(4) -0.0010(5) 0.0000(5) C29 0.0214(7) 0.0162(6) 0.0172(6) 0.0006(5) 0.0028(5) 0.0015(5) C30 0.0205(7) 0.0169(6) 0.0226(7) 0.0042(5) 0.0013(6) 0.0029(5) C31 0.0232(7) 0.0168(6) 0.0202(7) 0.0066(5) -0.0057(6) -0.0026(5) C32 0.0469(11) 0.0180(7) 0.0169(7) 0.0002(5) -0.0086(7) -0.0005(7) C33 0.0390(9) 0.0147(6) 0.0155(6) -0.0006(5) -0.0044(6) 0.0034(6) O34 0.0273(7) 0.0253(6) 0.0477(8) -0.0106(6) 0.0054(6) -0.0067(5) C34 0.0481(12) 0.0297(9) 0.0282(9) -0.0027(7) 0.0077(9) -0.0057(9) C35 0.0280(9) 0.0379(11) 0.0514(13) 0.0029(10) 0.0037(9) 0.0013(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C12 1.432(2) . ? O1 C11 1.445(2) . ? O2 C2 1.3653(17) . ? O2 C22 1.4271(18) . ? O3 C3 1.3689(17) . ? O3 C23 1.429(2) . ? O4 C9 1.2321(18) . ? N1 C9 1.3669(18) . ? N1 C6 1.4188(18) . ? N1 C8 1.4865(18) . ? N2 C16 1.5090(19) . ? N2 C15 1.5097(19) . ? N2 C21 1.5329(18) . ? N2 H24 0.9300 . ? C1 C2 1.3932(19) . ? C1 C6 1.3963(19) . ? C1 H1 0.9500 . ? C2 C3 1.4136(19) . ? C3 C4 1.3908(19) . ? C4 C5 1.3922(19) . ? C4 H4 0.9500 . ? C5 C6 1.3908(18) . ? C5 C7 1.5078(18) . ? C7 C21 1.5409(18) . ? C7 C17 1.5425(19) . ? C7 C8 1.5565(18) . ? C8 C18 1.5321(19) . ? C8 H8 1.0000 . ? C9 C10 1.515(2) . ? C10 C11 1.541(2) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C18 1.538(2) . ? C11 H11 1.0000 . ? C12 C13 1.500(3) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.330(2) . ? C13 H13 0.9500 . ? C14 C15 1.500(2) . ? C14 C19 1.525(2) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 C17 1.517(2) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 C19 1.536(2) . ? C18 H18 1.0000 . ? C19 C20 1.535(2) . ? C19 H19 1.0000 . ? C20 C21 1.516(2) . ? 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 1.2616(17) . ? O6 C24 1.2548(18) . ? O7 C26 1.4240(19) . ? O7 H7 0.8400 . ? O8 C27 1.2428(18) . ? O9 N4 1.224(2) . ? O10 N4 1.222(2) . ? N3 C27 1.3381(19) . ? N3 C25 1.4532(18) . ? N3 H3 0.8800 . ? N4 C31 1.468(2) . ? C24 C25 1.545(2) . ? C25 C26 1.535(2) . ? C25 H25 1.0000 . ? C26 H26A 0.9900 . ? C26 H26B 0.9900 . ? C27 C28 1.498(2) . ? C28 C33 1.389(2) . ? C28 C29 1.399(2) . ? C29 C30 1.389(2) . ? C29 H29 0.9500 . ? C30 C31 1.387(2) . ? C30 H30 0.9500 . ? C31 C32 1.384(2) . ? C32 C33 1.391(2) . ? C32 H32 0.9500 . ? C33 H33 0.9500 . ? O34 C34 1.417(3) . ? O34 H34 0.8400 . ? C34 C35 1.491(3) . ? C34 H34A 0.9900 . ? C34 H34B 0.9900 . ? C35 H35A 0.9800 . ? C35 H35B 0.9800 . ? C35 H35C 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 C12 O1 C11 115.49(15) . . ? C2 O2 C22 116.65(11) . . ? C3 O3 C23 116.81(12) . . ? C9 N1 C6 125.36(12) . . ? C9 N1 C8 118.64(11) . . ? C6 N1 C8 109.46(10) . . ? C16 N2 C15 111.76(11) . . ? C16 N2 C21 107.56(10) . . ? C15 N2 C21 113.84(11) . . ? C16 N2 H24 107.8 . . ? C15 N2 H24 107.8 . . ? C21 N2 H24 107.8 . . ? C2 C1 C6 117.74(12) . . ? C2 C1 H1 121.1 . . ? C6 C1 H1 121.1 . . ? O2 C2 C1 124.07(13) . . ? O2 C2 C3 114.92(12) . . ? C1 C2 C3 121.01(12) . . ? O3 C3 C4 124.68(13) . . ? O3 C3 C2 115.19(12) . . ? C4 C3 C2 120.13(12) . . ? C3 C4 C5 118.97(13) . . ? C3 C4 H4 120.5 . . ? C5 C4 H4 120.5 . . ? C6 C5 C4 120.49(12) . . ? C6 C5 C7 110.36(11) . . ? C4 C5 C7 128.93(12) . . ? C5 C6 C1 121.63(12) . . ? C5 C6 N1 109.90(12) . . ? C1 C6 N1 128.46(12) . . ? C5 C7 C21 115.50(11) . . ? C5 C7 C17 111.80(11) . . ? C21 C7 C17 102.00(10) . . ? C5 C7 C8 102.62(10) . . ? C21 C7 C8 114.23(11) . . ? C17 C7 C8 111.00(11) . . ? N1 C8 C18 106.29(10) . . ? N1 C8 C7 104.47(10) . . ? C18 C8 C7 116.51(11) . . ? N1 C8 H8 109.8 . . ? C18 C8 H8 109.8 . . ? C7 C8 H8 109.8 . . ? O4 C9 N1 122.70(14) . . ? O4 C9 C10 122.21(13) . . ? N1 C9 C10 115.06(12) . . ? C9 C10 C11 116.28(12) . . ? 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 115.00(12) . . ? O1 C11 C10 102.70(13) . . ? C18 C11 C10 110.39(12) . . ? O1 C11 H11 109.5 . . ? C18 C11 H11 109.5 . . ? C10 C11 H11 109.5 . . ? O1 C12 C13 111.05(15) . . ? 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 121.76(16) . . ? C14 C13 H13 119.1 . . ? C12 C13 H13 119.1 . . ? C13 C14 C15 121.16(15) . . ? C13 C14 C19 122.82(14) . . ? C15 C14 C19 116.01(13) . . ? C14 C15 N2 109.93(11) . . ? 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 104.81(11) . . ? N2 C16 H16A 110.8 . . ? C17 C16 H16A 110.8 . . ? N2 C16 H16B 110.8 . . ? C17 C16 H16B 110.8 . . ? H16A C16 H16B 108.9 . . ? C16 C17 C7 103.00(11) . . ? 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 C19 112.80(11) . . ? C8 C18 C11 107.72(12) . . ? C19 C18 C11 118.11(12) . . ? C8 C18 H18 105.8 . . ? C19 C18 H18 105.8 . . ? C11 C18 H18 105.8 . . ? C14 C19 C20 109.20(12) . . ? C14 C19 C18 113.73(12) . . ? C20 C19 C18 106.66(11) . . ? C14 C19 H19 109.1 . . ? C20 C19 H19 109.1 . . ? C18 C19 H19 109.1 . . ? C21 C20 C19 108.33(11) . . ? 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 110.56(11) . . ? C20 C21 C7 116.05(11) . . ? N2 C21 C7 104.72(10) . . ? C20 C21 H21 108.4 . . ? N2 C21 H21 108.4 . . ? C7 C21 H21 108.4 . . ? 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 . . ? C26 O7 H7 109.5 . . ? C27 N3 C25 120.80(12) . . ? C27 N3 H3 119.6 . . ? C25 N3 H3 119.6 . . ? O10 N4 O9 124.15(16) . . ? O10 N4 C31 117.78(17) . . ? O9 N4 C31 118.02(17) . . ? O6 C24 O5 125.56(14) . . ? O6 C24 C25 120.10(13) . . ? O5 C24 C25 114.34(12) . . ? N3 C25 C26 109.32(11) . . ? N3 C25 C24 112.84(12) . . ? C26 C25 C24 110.62(12) . . ? N3 C25 H25 108.0 . . ? C26 C25 H25 108.0 . . ? C24 C25 H25 108.0 . . ? O7 C26 C25 112.39(13) . . ? O7 C26 H26A 109.1 . . ? C25 C26 H26A 109.1 . . ? O7 C26 H26B 109.1 . . ? C25 C26 H26B 109.1 . . ? H26A C26 H26B 107.9 . . ? O8 C27 N3 122.87(13) . . ? O8 C27 C28 121.28(13) . . ? N3 C27 C28 115.82(12) . . ? C33 C28 C29 120.06(13) . . ? C33 C28 C27 121.64(13) . . ? C29 C28 C27 118.30(13) . . ? C30 C29 C28 120.48(14) . . ? C30 C29 H29 119.8 . . ? C28 C29 H29 119.8 . . ? C31 C30 C29 117.64(14) . . ? C31 C30 H30 121.2 . . ? C29 C30 H30 121.2 . . ? C32 C31 C30 123.43(14) . . ? C32 C31 N4 117.84(15) . . ? C30 C31 N4 118.70(15) . . ? C31 C32 C33 117.90(15) . . ? C31 C32 H32 121.0 . . ? C33 C32 H32 121.0 . . ? C28 C33 C32 120.42(15) . . ? C28 C33 H33 119.8 . . ? C32 C33 H33 119.8 . . ? C34 O34 H34 109.5 . . ? O34 C34 C35 110.69(18) . . ? O34 C34 H34A 109.5 . . ? C35 C34 H34A 109.5 . . ? O34 C34 H34B 109.5 . . ? C35 C34 H34B 109.5 . . ? H34A C34 H34B 108.1 . . ? C34 C35 H35A 109.5 . . ? C34 C35 H35B 109.5 . . ? H35A C35 H35B 109.5 . . ? C34 C35 H35C 109.5 . . ? H35A C35 H35C 109.5 . . ? H35B C35 H35C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C22 O2 C2 C1 -10.2(2) . . . . ? C22 O2 C2 C3 169.56(13) . . . . ? C6 C1 C2 O2 178.96(13) . . . . ? C6 C1 C2 C3 -0.8(2) . . . . ? C23 O3 C3 C4 1.9(2) . . . . ? C23 O3 C3 C2 -177.21(14) . . . . ? O2 C2 C3 O3 -1.48(18) . . . . ? C1 C2 C3 O3 178.29(13) . . . . ? O2 C2 C3 C4 179.40(13) . . . . ? C1 C2 C3 C4 -0.8(2) . . . . ? O3 C3 C4 C5 -177.61(14) . . . . ? C2 C3 C4 C5 1.4(2) . . . . ? C3 C4 C5 C6 -0.4(2) . . . . ? C3 C4 C5 C7 -174.47(13) . . . . ? C4 C5 C6 C1 -1.3(2) . . . . ? C7 C5 C6 C1 173.82(12) . . . . ? C4 C5 C6 N1 177.65(12) . . . . ? C7 C5 C6 N1 -7.26(15) . . . . ? C2 C1 C6 C5 1.8(2) . . . . ? C2 C1 C6 N1 -176.87(13) . . . . ? C9 N1 C6 C5 -155.85(13) . . . . ? C8 N1 C6 C5 -4.91(15) . . . . ? C9 N1 C6 C1 23.0(2) . . . . ? C8 N1 C6 C1 173.92(13) . . . . ? C6 C5 C7 C21 140.46(12) . . . . ? C4 C5 C7 C21 -44.98(19) . . . . ? C6 C5 C7 C17 -103.51(13) . . . . ? C4 C5 C7 C17 71.05(18) . . . . ? C6 C5 C7 C8 15.52(14) . . . . ? C4 C5 C7 C8 -169.92(14) . . . . ? C9 N1 C8 C18 43.74(16) . . . . ? C6 N1 C8 C18 -109.43(12) . . . . ? C9 N1 C8 C7 167.49(12) . . . . ? C6 N1 C8 C7 14.32(13) . . . . ? C5 C7 C8 N1 -17.41(12) . . . . ? C21 C7 C8 N1 -143.19(11) . . . . ? C17 C7 C8 N1 102.17(12) . . . . ? C5 C7 C8 C18 99.48(13) . . . . ? C21 C7 C8 C18 -26.29(16) . . . . ? C17 C7 C8 C18 -140.94(11) . . . . ? C6 N1 C9 O4 -21.4(2) . . . . ? C8 N1 C9 O4 -169.99(15) . . . . ? C6 N1 C9 C10 160.50(13) . . . . ? C8 N1 C9 C10 11.95(19) . . . . ? O4 C9 C10 C11 138.94(16) . . . . ? N1 C9 C10 C11 -42.99(19) . . . . ? C12 O1 C11 C18 -64.97(18) . . . . ? C12 O1 C11 C10 175.07(13) . . . . ? C9 C10 C11 O1 136.52(13) . . . . ? C9 C10 C11 C18 13.43(19) . . . . ? C11 O1 C12 C13 87.62(19) . . . . ? O1 C12 C13 C14 -66.6(2) . . . . ? C12 C13 C14 C15 179.26(16) . . . . ? C12 C13 C14 C19 -1.4(3) . . . . ? C13 C14 C15 N2 -128.07(16) . . . . ? C19 C14 C15 N2 52.58(17) . . . . ? C16 N2 C15 C14 77.42(15) . . . . ? C21 N2 C15 C14 -44.70(16) . . . . ? C15 N2 C16 C17 -142.13(11) . . . . ? C21 N2 C16 C17 -16.47(14) . . . . ? N2 C16 C17 C7 36.56(13) . . . . ? C5 C7 C17 C16 -166.37(11) . . . . ? C21 C7 C17 C16 -42.38(13) . . . . ? C8 C7 C17 C16 79.69(13) . . . . ? N1 C8 C18 C19 157.04(11) . . . . ? C7 C8 C18 C19 41.16(16) . . . . ? N1 C8 C18 C11 -70.82(13) . . . . ? C7 C8 C18 C11 173.29(11) . . . . ? O1 C11 C18 C8 -74.67(15) . . . . ? C10 C11 C18 C8 40.94(16) . . . . ? O1 C11 C18 C19 54.53(18) . . . . ? C10 C11 C18 C19 170.14(12) . . . . ? C13 C14 C19 C20 178.69(15) . . . . ? C15 C14 C19 C20 -1.97(17) . . . . ? C13 C14 C19 C18 59.7(2) . . . . ? C15 C14 C19 C18 -120.96(13) . . . . ? C8 C18 C19 C14 59.06(16) . . . . ? C11 C18 C19 C14 -67.73(16) . . . . ? C8 C18 C19 C20 -61.37(15) . . . . ? C11 C18 C19 C20 171.84(12) . . . . ? C14 C19 C20 C21 -55.52(15) . . . . ? C18 C19 C20 C21 67.78(14) . . . . ? C19 C20 C21 N2 63.11(14) . . . . ? C19 C20 C21 C7 -55.93(16) . . . . ? C16 N2 C21 C20 -135.75(12) . . . . ? C15 N2 C21 C20 -11.35(15) . . . . ? C16 N2 C21 C7 -10.06(14) . . . . ? C15 N2 C21 C7 114.35(12) . . . . ? C5 C7 C21 C20 -84.36(15) . . . . ? C17 C7 C21 C20 154.17(12) . . . . ? C8 C7 C21 C20 34.34(16) . . . . ? C5 C7 C21 N2 153.45(11) . . . . ? C17 C7 C21 N2 31.98(13) . . . . ? C8 C7 C21 N2 -87.85(13) . . . . ? C27 N3 C25 C26 168.52(13) . . . . ? C27 N3 C25 C24 -67.94(17) . . . . ? O6 C24 C25 N3 -22.06(19) . . . . ? O5 C24 C25 N3 158.57(12) . . . . ? O6 C24 C25 C26 100.76(15) . . . . ? O5 C24 C25 C26 -78.61(15) . . . . ? N3 C25 C26 O7 -61.08(15) . . . . ? C24 C25 C26 O7 174.07(12) . . . . ? C25 N3 C27 O8 1.7(2) . . . . ? C25 N3 C27 C28 -176.49(12) . . . . ? O8 C27 C28 C33 149.42(16) . . . . ? N3 C27 C28 C33 -32.3(2) . . . . ? O8 C27 C28 C29 -31.1(2) . . . . ? N3 C27 C28 C29 147.13(14) . . . . ? C33 C28 C29 C30 2.3(2) . . . . ? C27 C28 C29 C30 -177.14(15) . . . . ? C28 C29 C30 C31 -2.5(2) . . . . ? C29 C30 C31 C32 0.6(3) . . . . ? C29 C30 C31 N4 -177.74(16) . . . . ? O10 N4 C31 C32 -25.8(3) . . . . ? O9 N4 C31 C32 156.43(19) . . . . ? O10 N4 C31 C30 152.59(17) . . . . ? O9 N4 C31 C30 -25.1(3) . . . . ? C30 C31 C32 C33 1.4(3) . . . . ? N4 C31 C32 C33 179.79(18) . . . . ? C29 C28 C33 C32 -0.2(3) . . . . ? C27 C28 C33 C32 179.23(17) . . . . ? C31 C32 C33 C28 -1.6(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 1.72 2.6333(17) 167.0 . O7 H7 O6 0.84 1.94 2.7602(17) 164.8 4_456 N3 H3 O6 0.88 2.09 2.8980(17) 151.9 4_456 O34 H34 O8 0.84 2.03 2.8362(19) 160.3 . C16 H16A O4 0.99 2.45 3.108(2) 123.3 1_455 C22 H22A O4 0.98 2.44 3.3957(19) 163.5 3_746 C16 H16B O2 0.99 2.45 3.2674(18) 139.1 3_656 C17 H17B O3 0.99 2.59 3.5328(19) 158.7 3_656 _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 34.00 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.807 _refine_diff_density_min -0.206 _refine_diff_density_rms 0.053 #===== end data_12 _database_code_depnum_ccdc_archive 'CCDC 758153' #TrackingRef 'bialonska2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; brucinium N-(4-nitrobenzoyl)-L-serinate ethanol solvate ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C23 H27 N2 O4, C10 H9 N2 O6, C2 H6 O' _chemical_formula_sum 'C35 H42 N4 O11' _chemical_formula_weight 694.73 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 9.641(2) _cell_length_b 10.308(2) _cell_length_c 33.653(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3344.4(10) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 16481 _cell_measurement_theta_min 2.88 _cell_measurement_theta_max 35.25 _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.40 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.380 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1472 _exptl_absorpt_coefficient_mu 0.103 _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 44729 _diffrn_reflns_av_R_equivalents 0.0613 _diffrn_reflns_av_sigmaI/netI 0.0371 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -43 _diffrn_reflns_limit_l_max 43 _diffrn_reflns_theta_min 2.89 _diffrn_reflns_theta_max 27.50 _reflns_number_total 4320 _reflns_number_gt 3325 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET) (compiled May 8 2007,13:10:02) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET) (compiled May 8 2007,13:10:02) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET) (compiled May 8 2007,13:10:02) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0703P)^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 4320 _refine_ls_number_parameters 614 _refine_ls_number_restraints 240 _refine_ls_R_factor_all 0.0561 _refine_ls_R_factor_gt 0.0397 _refine_ls_wR_factor_ref 0.1095 _refine_ls_wR_factor_gt 0.0980 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.046 _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 0.0119(2) -0.04281(17) 0.55923(6) 0.0381(5) Uani 1 1 d . . . O2 O 0.3303(2) 0.73015(17) 0.51030(5) 0.0337(5) Uani 1 1 d . . . O3 O 0.4673(2) 0.72411(16) 0.57614(5) 0.0304(4) Uani 1 1 d . . . O4 O 0.0735(3) 0.3227(2) 0.47836(6) 0.0483(6) Uani 1 1 d . . . N1 N 0.1276(2) 0.3030(2) 0.54400(6) 0.0291(5) Uani 1 1 d . . . N2 N 0.2747(2) 0.1620(2) 0.66731(6) 0.0258(5) Uani 1 1 d . . . H2A H 0.3226 0.1869 0.6893 0.031 Uiso 1 1 calc R . . C1 C 0.2203(3) 0.5221(2) 0.52288(7) 0.0283(6) Uani 1 1 d . . . H1A H 0.1687 0.5256 0.4996 0.034 Uiso 1 1 calc R . . C2 C 0.3094(3) 0.6217(2) 0.53312(7) 0.0258(6) Uani 1 1 d . . . C3 C 0.3852(3) 0.6178(2) 0.56919(7) 0.0242(5) Uani 1 1 d . . . C4 C 0.3701(3) 0.5134(2) 0.59462(7) 0.0223(5) Uani 1 1 d . . . H4A H 0.4177 0.5115 0.6186 0.027 Uiso 1 1 calc R . . C5 C 0.2832(3) 0.4111(2) 0.58410(7) 0.0223(5) Uani 1 1 d . . . C6 C 0.2099(3) 0.4159(2) 0.54860(7) 0.0247(5) Uani 1 1 d . . . C7 C 0.2356(3) 0.2964(2) 0.60857(7) 0.0222(5) Uani 1 1 d . . . C8 C 0.1527(3) 0.2137(2) 0.57766(7) 0.0258(5) Uani 1 1 d . . . H8A H 0.0636 0.1881 0.5893 0.031 Uiso 1 1 calc R . . C9 C 0.0808(3) 0.2557(3) 0.50839(8) 0.0360(7) Uani 1 1 d . . . C10 C 0.0360(3) 0.1144(3) 0.50841(9) 0.0390(7) Uani 1 1 d . . . H10A H 0.0428 0.0823 0.4814 0.047 Uiso 1 1 calc R . . H10B H -0.0612 0.1112 0.5159 0.047 Uiso 1 1 calc R . . C11 C 0.1164(3) 0.0199(3) 0.53574(8) 0.0332(6) Uani 1 1 d . . . H11A H 0.1634 -0.0451 0.5193 0.040 Uiso 1 1 calc R . . C12 C 0.0613(3) -0.1514(3) 0.58217(10) 0.0409(7) Uani 1 1 d . . . H12A H 0.1365 -0.1936 0.5680 0.049 Uiso 1 1 calc R . . H12B H -0.0130 -0.2139 0.5854 0.049 Uiso 1 1 calc R . . C13 C 0.1116(3) -0.1087(3) 0.62239(9) 0.0342(6) Uani 1 1 d . . . H13A H 0.0648 -0.1372 0.6449 0.041 Uiso 1 1 calc R . . C14 C 0.2208(3) -0.0316(2) 0.62675(8) 0.0288(6) Uani 1 1 d . . . C15 C 0.2681(3) 0.0145(2) 0.66688(7) 0.0290(6) Uani 1 1 d . . . H15A H 0.3590 -0.0211 0.6727 0.035 Uiso 1 1 calc R . . H15B H 0.2040 -0.0154 0.6871 0.035 Uiso 1 1 calc R . . C16 C 0.1327(3) 0.2220(3) 0.66927(8) 0.0311(6) Uani 1 1 d . . . H16A H 0.1095 0.2460 0.6963 0.037 Uiso 1 1 calc R . . H16B H 0.0629 0.1624 0.6594 0.037 Uiso 1 1 calc R . . C17 C 0.1426(3) 0.3409(2) 0.64298(7) 0.0265(6) Uani 1 1 d . . . H17A H 0.1841 0.4130 0.6572 0.032 Uiso 1 1 calc R . . H17B H 0.0518 0.3667 0.6334 0.032 Uiso 1 1 calc R . . C18 C 0.2245(3) 0.0932(2) 0.56036(7) 0.0261(5) Uani 1 1 d . . . H18A H 0.2933 0.1257 0.5414 0.031 Uiso 1 1 calc R . . C19 C 0.3062(3) 0.0171(2) 0.59162(7) 0.0254(5) Uani 1 1 d . . . H19A H 0.3515 -0.0570 0.5788 0.030 Uiso 1 1 calc R . . C20 C 0.4183(3) 0.1110(2) 0.60708(7) 0.0248(5) Uani 1 1 d . . . H20A H 0.4833 0.0646 0.6239 0.030 Uiso 1 1 calc R . . H20B H 0.4692 0.1477 0.5849 0.030 Uiso 1 1 calc R . . C21 C 0.3487(3) 0.2185(2) 0.63065(7) 0.0220(5) Uani 1 1 d . . . H21A H 0.4203 0.2791 0.6398 0.026 Uiso 1 1 calc R . . C22 C 0.2497(4) 0.7388(3) 0.47468(7) 0.0420(8) Uani 1 1 d . . . H22A H 0.2716 0.8180 0.4610 0.063 Uiso 1 1 calc R . . H22B H 0.1528 0.7379 0.4813 0.063 Uiso 1 1 calc R . . H22C H 0.2705 0.6662 0.4578 0.063 Uiso 1 1 calc R . . C23 C 0.5272(3) 0.7349(3) 0.61481(9) 0.0387(7) Uani 1 1 d . . . H23A H 0.5822 0.8124 0.6162 0.058 Uiso 1 1 calc R . . H23B H 0.5848 0.6608 0.6199 0.058 Uiso 1 1 calc R . . H23C H 0.4547 0.7388 0.6343 0.058 Uiso 1 1 calc R . . O5 O 0.4427(2) 0.21413(16) 0.72822(5) 0.0353(5) Uani 1 1 d . B . O6 O 0.5293(3) 0.31221(18) 0.78222(6) 0.0509(7) Uani 1 1 d . B . O7 O 0.3487(3) 0.59451(19) 0.69141(6) 0.0472(6) Uani 1 1 d . B . H7 H 0.3787 0.6656 0.6981 0.071 Uiso 1 1 calc R . . N3 N 0.3490(3) 0.5199(2) 0.77467(6) 0.0314(5) Uani 1 1 d . . . H3 H 0.3957 0.5909 0.7752 0.038 Uiso 1 1 calc R A 1 C24 C 0.4513(3) 0.3085(2) 0.75288(8) 0.0339(7) Uani 1 1 d . . . C25 C 0.3643(3) 0.4274(2) 0.74206(7) 0.0317(6) Uani 1 1 d . B . H25 H 0.2719 0.3984 0.7338 0.038 Uiso 1 1 calc R . . C26 C 0.4334(4) 0.4962(2) 0.70737(7) 0.0357(7) Uani 1 1 d . . . H26A H 0.5202 0.5340 0.7162 0.043 Uiso 1 1 calc R B . H26B H 0.4544 0.4334 0.6868 0.043 Uiso 1 1 calc R . . O8 O 0.1955(10) 0.3909(6) 0.8072(3) 0.0443(16) Uani 0.675(5) 1 d PU B 1 O9 O 0.1837(4) 0.8460(4) 0.95868(10) 0.0424(10) Uani 0.675(5) 1 d P B 1 O10 O 0.2772(6) 0.9838(4) 0.91983(14) 0.0637(13) Uani 0.675(5) 1 d PU B 1 N4 N 0.2307(5) 0.8776(5) 0.92657(15) 0.0395(11) Uani 0.675(5) 1 d PU B 1 C27 C 0.2608(18) 0.4902(9) 0.8033(4) 0.0251(18) Uani 0.675(5) 1 d PU B 1 C28 C 0.2510(12) 0.5944(7) 0.8353(4) 0.0237(15) Uani 0.675(5) 1 d PU B 1 C29 C 0.2203(7) 0.5601(5) 0.87421(19) 0.0245(11) Uani 0.675(5) 1 d PU B 1 H29 H 0.2029 0.4735 0.8802 0.029 Uiso 0.675(5) 1 calc PR B 1 C30 C 0.2150(5) 0.6511(6) 0.90432(14) 0.0247(10) Uani 0.675(5) 1 d PU B 1 H30 H 0.1966 0.6267 0.9304 0.030 Uiso 0.675(5) 1 calc PR B 1 C31 C 0.2378(6) 0.7795(7) 0.89456(19) 0.0267(13) Uani 0.675(5) 1 d PU B 1 C32 C 0.2665(6) 0.8203(6) 0.85645(18) 0.0331(12) Uani 0.675(5) 1 d PU B 1 H32 H 0.2815 0.9074 0.8507 0.040 Uiso 0.675(5) 1 calc PR B 1 C33 C 0.2721(11) 0.7259(8) 0.8268(2) 0.0302(16) Uani 0.675(5) 1 d PU B 1 H33 H 0.2904 0.7510 0.8008 0.036 Uiso 0.675(5) 1 calc PR B 1 O8A O 0.169(2) 0.4323(14) 0.8080(6) 0.044(3) Uani 0.325(5) 1 d PU B 2 O9A O 0.2009(9) 0.9299(12) 0.9462(3) 0.060(2) Uani 0.325(5) 1 d PU B 2 O10C O 0.1864(9) 1.0567(9) 0.8962(3) 0.066(3) Uani 0.325(5) 1 d P B 2 N4A N 0.2012(11) 0.9552(15) 0.9096(3) 0.045(2) Uani 0.325(5) 1 d PU B 2 C27A C 0.259(4) 0.527(2) 0.8066(9) 0.029(4) Uani 0.325(5) 1 d PU B 2 C28A C 0.254(2) 0.6401(15) 0.8318(7) 0.021(3) Uani 0.325(5) 1 d PU B 2 C29A C 0.2281(15) 0.6176(12) 0.8716(4) 0.034(3) Uani 0.325(5) 1 d PU B 2 H29A H 0.2176 0.5331 0.8808 0.041 Uiso 0.325(5) 1 calc PR B 2 C30A C 0.2182(12) 0.7208(16) 0.8980(3) 0.025(2) Uani 0.325(5) 1 d PU B 2 H30A H 0.2056 0.7076 0.9251 0.030 Uiso 0.325(5) 1 calc PR B 2 C31A C 0.2275(13) 0.8409(15) 0.8825(4) 0.038(3) Uani 0.325(5) 1 d PU B 2 C32A C 0.2461(13) 0.8689(13) 0.8428(4) 0.040(3) Uani 0.325(5) 1 d PU B 2 H32A H 0.2491 0.9539 0.8336 0.048 Uiso 0.325(5) 1 calc PR B 2 C33A C 0.260(2) 0.7635(19) 0.8173(5) 0.033(3) Uani 0.325(5) 1 d PU B 2 H33A H 0.2744 0.7773 0.7903 0.039 Uiso 0.325(5) 1 calc PR B 2 O34 O 0.0198(9) 0.2630(7) 0.75901(18) 0.071(2) Uani 0.40 1 d PDU C 1 C35 C 0.1282(13) 0.0712(11) 0.7856(3) 0.065(2) Uani 0.40 1 d PDU C 1 O34A O 0.2112(12) 0.1138(10) 0.8161(4) 0.052(3) Uani 0.20 1 d PDU C 2 C35A C 0.0624(14) 0.109(2) 0.8145(5) 0.086(4) Uani 0.20 1 d PDU C 2 O34B O 0.1329(15) 0.180(2) 0.7669(6) 0.069(4) Uani 0.15 1 d PDU C 3 C35B C 0.055(3) 0.0042(14) 0.7705(8) 0.069(5) Uani 0.15 1 d PDU C 3 C34 C -0.0054(9) 0.1361(8) 0.7757(2) 0.091(2) Uani 0.75 1 d PDU . . C341 C 0.0428(14) 0.1126(19) 0.7901(5) 0.060(3) Uani 0.25 1 d PDU C 4 O341 O 0.1838(12) 0.1241(12) 0.7769(3) 0.054(2) Uani 0.25 1 d PDU C 4 C351 C -0.0577(19) 0.2054(19) 0.7720(5) 0.068(3) Uani 0.25 1 d PDU C 4 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 0.0319(12) 0.0298(9) 0.0527(12) -0.0026(9) -0.0068(9) -0.0050(9) O2 0.0458(12) 0.0300(9) 0.0254(9) 0.0081(8) 0.0005(8) 0.0089(9) O3 0.0359(11) 0.0227(8) 0.0326(10) 0.0029(7) -0.0003(8) -0.0030(8) O4 0.0685(16) 0.0438(11) 0.0327(11) -0.0024(10) -0.0256(11) 0.0064(12) N1 0.0306(13) 0.0299(11) 0.0269(11) -0.0030(9) -0.0102(9) 0.0010(10) N2 0.0300(13) 0.0269(10) 0.0206(10) 0.0011(9) 0.0052(9) -0.0016(10) C1 0.0343(16) 0.0313(13) 0.0192(11) -0.0037(10) -0.0041(10) 0.0134(12) C2 0.0324(15) 0.0252(12) 0.0199(12) 0.0046(10) 0.0035(10) 0.0107(12) C3 0.0265(14) 0.0217(11) 0.0242(12) -0.0011(9) 0.0047(10) 0.0048(11) C4 0.0242(14) 0.0245(12) 0.0181(11) -0.0021(9) -0.0011(9) 0.0047(11) C5 0.0256(14) 0.0236(12) 0.0177(11) -0.0014(9) 0.0018(9) 0.0040(11) C6 0.0255(14) 0.0264(12) 0.0221(12) -0.0048(10) -0.0026(10) 0.0059(11) C7 0.0211(13) 0.0246(12) 0.0208(11) -0.0036(9) 0.0007(9) -0.0010(11) C8 0.0206(13) 0.0295(13) 0.0274(12) -0.0018(11) -0.0036(10) -0.0015(12) C9 0.0349(17) 0.0414(15) 0.0318(15) -0.0071(13) -0.0134(12) 0.0033(14) C10 0.0356(17) 0.0433(16) 0.0381(15) -0.0097(13) -0.0153(13) -0.0036(15) C11 0.0293(16) 0.0351(14) 0.0351(15) -0.0092(12) -0.0053(11) -0.0019(13) C12 0.0330(17) 0.0282(13) 0.0615(19) -0.0033(14) -0.0073(14) -0.0044(13) C13 0.0298(16) 0.0266(13) 0.0461(17) 0.0018(12) 0.0025(12) -0.0021(12) C14 0.0287(15) 0.0239(12) 0.0339(14) 0.0003(11) 0.0035(11) 0.0029(12) C15 0.0343(16) 0.0245(12) 0.0283(13) 0.0043(10) 0.0039(11) -0.0025(12) C16 0.0307(16) 0.0323(13) 0.0302(14) -0.0013(11) 0.0081(11) -0.0015(13) C17 0.0215(14) 0.0287(13) 0.0294(13) -0.0008(11) 0.0034(10) 0.0004(11) C18 0.0259(14) 0.0259(12) 0.0265(12) -0.0060(10) -0.0014(10) -0.0020(12) C19 0.0239(14) 0.0255(12) 0.0268(13) -0.0043(10) 0.0004(10) 0.0008(11) C20 0.0222(13) 0.0276(12) 0.0245(12) -0.0003(10) 0.0021(10) 0.0005(11) C21 0.0208(13) 0.0258(11) 0.0194(11) 0.0038(10) 0.0002(9) -0.0052(11) C22 0.069(2) 0.0359(14) 0.0213(13) 0.0056(11) -0.0011(14) 0.0195(16) C23 0.0451(18) 0.0273(13) 0.0438(16) 0.0031(12) -0.0123(14) -0.0083(13) O5 0.0569(14) 0.0243(8) 0.0248(9) -0.0023(7) -0.0079(9) -0.0014(10) O6 0.0880(19) 0.0266(10) 0.0381(12) -0.0026(9) -0.0281(12) 0.0009(12) O7 0.0849(18) 0.0265(10) 0.0301(10) 0.0006(8) -0.0167(11) 0.0026(12) N3 0.0452(15) 0.0284(11) 0.0206(11) -0.0061(9) -0.0011(10) -0.0008(11) C24 0.053(2) 0.0263(13) 0.0225(13) 0.0004(10) -0.0032(12) -0.0054(13) C25 0.0526(19) 0.0237(12) 0.0188(12) -0.0041(10) -0.0028(12) -0.0043(13) C26 0.064(2) 0.0231(12) 0.0202(12) -0.0034(10) -0.0001(13) 0.0016(14) O8 0.056(4) 0.039(3) 0.039(2) -0.010(3) -0.001(2) -0.010(3) O9 0.041(2) 0.055(2) 0.0310(18) -0.0140(17) 0.0115(14) -0.0019(18) O10 0.084(4) 0.046(2) 0.061(3) -0.0219(19) 0.023(3) -0.016(2) N4 0.034(2) 0.046(2) 0.039(2) -0.018(2) 0.0102(18) -0.005(2) C27 0.041(3) 0.019(5) 0.015(2) -0.013(3) -0.002(2) -0.002(5) C28 0.027(2) 0.017(4) 0.027(3) -0.006(4) -0.0026(19) -0.004(4) C29 0.017(2) 0.030(3) 0.026(2) -0.003(3) -0.0007(16) -0.005(3) C30 0.019(2) 0.035(3) 0.021(2) -0.003(2) 0.0011(15) -0.003(2) C31 0.025(3) 0.029(4) 0.026(3) -0.006(3) 0.005(2) -0.006(3) C32 0.032(3) 0.030(3) 0.037(4) -0.003(2) 0.009(2) 0.002(2) C33 0.038(3) 0.029(5) 0.024(4) 0.003(3) 0.005(3) 0.009(4) O8A 0.048(6) 0.052(7) 0.032(4) -0.012(5) 0.015(4) -0.009(6) O9A 0.054(5) 0.082(6) 0.043(5) -0.025(5) 0.014(4) -0.012(5) O10C 0.061(6) 0.061(6) 0.077(6) -0.046(5) 0.010(5) -0.003(5) N4A 0.026(5) 0.068(6) 0.042(5) -0.029(5) -0.002(4) -0.006(5) C27A 0.035(6) 0.016(10) 0.037(7) -0.016(7) 0.000(5) -0.006(9) C28A 0.026(5) 0.017(8) 0.019(5) -0.007(8) 0.001(4) -0.003(8) C29A 0.024(5) 0.040(6) 0.037(5) 0.000(6) -0.006(4) -0.006(6) C30A 0.019(4) 0.037(7) 0.019(4) 0.002(6) 0.000(3) -0.008(6) C31A 0.022(5) 0.056(7) 0.036(6) -0.015(5) 0.009(4) -0.009(6) C32A 0.029(5) 0.040(6) 0.050(7) -0.014(5) 0.005(5) 0.001(5) C33A 0.034(6) 0.035(9) 0.029(8) -0.001(5) 0.005(6) 0.001(7) O34 0.083(5) 0.085(4) 0.045(3) -0.004(3) 0.012(3) -0.040(4) C35 0.075(6) 0.066(5) 0.052(5) 0.012(4) -0.019(5) -0.020(5) O34A 0.048(6) 0.028(5) 0.080(7) 0.012(5) -0.017(5) -0.014(5) C35A 0.088(7) 0.073(6) 0.096(7) 0.017(7) -0.008(7) -0.016(7) O34B 0.073(8) 0.086(8) 0.048(7) -0.010(7) 0.013(6) -0.031(7) C35B 0.087(11) 0.061(10) 0.058(10) 0.006(9) 0.019(10) -0.031(10) C34 0.094(5) 0.089(4) 0.090(4) 0.008(4) 0.017(4) -0.032(4) C341 0.069(6) 0.063(5) 0.048(5) 0.010(5) 0.006(5) -0.015(5) O341 0.052(5) 0.054(5) 0.056(5) 0.011(4) 0.003(4) -0.003(4) C351 0.069(6) 0.072(6) 0.061(5) -0.002(6) 0.006(5) -0.013(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(4) . ? O1 C12 1.441(3) . ? O2 C2 1.371(3) . ? O2 C22 1.432(3) . ? O3 C3 1.372(3) . ? O3 C23 1.428(3) . ? O4 C9 1.226(4) . ? N1 C9 1.370(3) . ? N1 C6 1.418(3) . ? N1 C8 1.480(3) . ? N2 C16 1.504(4) . ? N2 C15 1.523(3) . ? N2 C21 1.539(3) . ? N2 H2A 0.9100 . ? C1 C2 1.383(4) . ? C1 C6 1.399(4) . ? C1 H1A 0.9300 . ? C2 C3 1.417(4) . ? C3 C4 1.383(3) . ? C4 C5 1.392(3) . ? C4 H4A 0.9300 . ? C5 C6 1.389(3) . ? C5 C7 1.512(3) . ? C7 C17 1.535(3) . ? C7 C21 1.544(3) . ? C7 C8 1.564(3) . ? C8 C18 1.537(4) . ? C8 H8A 0.9800 . ? C9 C10 1.519(4) . ? C10 C11 1.548(4) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C18 1.531(4) . ? C11 H11A 0.9800 . ? C12 C13 1.504(4) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C14 1.327(4) . ? C13 H13A 0.9300 . ? C14 C15 1.502(4) . ? C14 C19 1.526(4) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 C17 1.515(4) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 C19 1.530(4) . ? C18 H18A 0.9800 . ? C19 C20 1.541(4) . ? C19 H19A 0.9800 . ? C20 C21 1.520(3) . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C21 H21A 0.9800 . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? O5 C24 1.281(3) . ? O6 C24 1.241(3) . ? O7 C26 1.408(3) . ? O7 H7 0.8200 . ? N3 C27 1.321(16) . ? N3 C27A 1.39(3) . ? N3 C25 1.461(3) . ? N3 H3 0.8600 . ? C24 C25 1.530(4) . ? C25 C26 1.520(4) . ? C25 H25 0.9800 . ? C26 H26A 0.9700 . ? C26 H26B 0.9700 . ? O8 C27 1.209(17) . ? O9 N4 1.216(6) . ? O10 N4 1.204(6) . ? N4 C31 1.479(7) . ? C27 C28 1.523(12) . ? C28 C29 1.389(13) . ? C28 C33 1.400(8) . ? C29 C30 1.382(8) . ? C29 H29 0.9300 . ? C30 C31 1.381(7) . ? C30 H30 0.9300 . ? C31 C32 1.378(8) . ? C32 C33 1.394(11) . ? C32 H32 0.9300 . ? C33 H33 0.9300 . ? O8A C27A 1.31(4) . ? O9A N4A 1.258(15) . ? O10C N4A 1.149(16) . ? N4A C31A 1.513(17) . ? C27A C28A 1.44(2) . ? C28A C33A 1.365(16) . ? C28A C29A 1.38(3) . ? C29A C30A 1.388(18) . ? C29A H29A 0.9300 . ? C30A C31A 1.347(17) . ? C30A H30A 0.9300 . ? C31A C32A 1.376(18) . ? C32A C33A 1.39(2) . ? C32A H32A 0.9300 . ? C33A H33A 0.9300 . ? O34 C34 1.444(8) . ? C35 C34 1.489(12) . ? O34A C35A 1.437(9) . ? C35A C34 1.487(12) . ? O34B C34 1.438(9) . ? C35B C34 1.491(13) . ? C34 C341 0.715(17) . ? C34 C351 0.884(16) . ? C34 O341 1.828(15) . ? C341 O341 1.435(9) . ? C341 C351 1.492(13) . ? 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 114.4(2) . . ? C2 O2 C22 116.1(2) . . ? C3 O3 C23 116.79(19) . . ? C9 N1 C6 124.9(2) . . ? C9 N1 C8 120.2(2) . . ? C6 N1 C8 109.60(19) . . ? C16 N2 C15 111.9(2) . . ? C16 N2 C21 107.55(19) . . ? C15 N2 C21 112.93(19) . . ? C16 N2 H2A 108.1 . . ? C15 N2 H2A 108.1 . . ? C21 N2 H2A 108.1 . . ? C2 C1 C6 118.1(2) . . ? C2 C1 H1A 121.0 . . ? C6 C1 H1A 121.0 . . ? O2 C2 C1 123.9(2) . . ? O2 C2 C3 115.3(2) . . ? C1 C2 C3 120.9(2) . . ? O3 C3 C4 125.2(2) . . ? O3 C3 C2 114.9(2) . . ? C4 C3 C2 119.8(2) . . ? C3 C4 C5 119.7(2) . . ? C3 C4 H4A 120.1 . . ? C5 C4 H4A 120.1 . . ? C6 C5 C4 119.8(2) . . ? C6 C5 C7 110.0(2) . . ? C4 C5 C7 129.5(2) . . ? C5 C6 C1 121.6(2) . . ? C5 C6 N1 110.4(2) . . ? C1 C6 N1 128.0(2) . . ? C5 C7 C17 110.75(19) . . ? C5 C7 C21 117.0(2) . . ? C17 C7 C21 101.82(18) . . ? C5 C7 C8 102.65(18) . . ? C17 C7 C8 111.5(2) . . ? C21 C7 C8 113.4(2) . . ? N1 C8 C18 106.65(19) . . ? N1 C8 C7 104.71(19) . . ? C18 C8 C7 117.5(2) . . ? N1 C8 H8A 109.2 . . ? C18 C8 H8A 109.2 . . ? C7 C8 H8A 109.2 . . ? O4 C9 N1 122.6(3) . . ? O4 C9 C10 121.6(2) . . ? N1 C9 C10 115.7(2) . . ? C9 C10 C11 117.5(2) . . ? 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 113.7(2) . . ? O1 C11 C10 105.0(2) . . ? C18 C11 C10 110.6(2) . . ? O1 C11 H11A 109.1 . . ? C18 C11 H11A 109.1 . . ? C10 C11 H11A 109.1 . . ? O1 C12 C13 111.2(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 122.1(3) . . ? C14 C13 H13A 119.0 . . ? C12 C13 H13A 119.0 . . ? C13 C14 C15 122.0(2) . . ? C13 C14 C19 122.6(2) . . ? C15 C14 C19 115.4(2) . . ? C14 C15 N2 109.7(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 104.5(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 103.6(2) . . ? C16 C17 H17A 111.0 . . ? C7 C17 H17A 111.0 . . ? C16 C17 H17B 111.0 . . ? C7 C17 H17B 111.0 . . ? H17A C17 H17B 109.0 . . ? C19 C18 C11 118.0(2) . . ? C19 C18 C8 112.68(19) . . ? C11 C18 C8 107.3(2) . . ? C19 C18 H18A 106.0 . . ? C11 C18 H18A 106.0 . . ? C8 C18 H18A 106.0 . . ? C14 C19 C18 115.1(2) . . ? C14 C19 C20 108.9(2) . . ? C18 C19 C20 105.7(2) . . ? C14 C19 H19A 109.0 . . ? C18 C19 H19A 109.0 . . ? C20 C19 H19A 109.0 . . ? C21 C20 C19 108.9(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 N2 110.33(19) . . ? C20 C21 C7 116.09(19) . . ? N2 C21 C7 104.78(19) . . ? C20 C21 H21A 108.5 . . ? N2 C21 H21A 108.5 . . ? C7 C21 H21A 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 . . ? C26 O7 H7 109.5 . . ? C27 N3 C27A 16.5(11) . . ? C27 N3 C25 117.5(5) . . ? C27A N3 C25 132.8(11) . . ? C27 N3 H3 121.2 . . ? C27A N3 H3 105.6 . . ? C25 N3 H3 121.2 . . ? O6 C24 O5 125.3(3) . . ? O6 C24 C25 119.8(2) . . ? O5 C24 C25 114.7(2) . . ? N3 C25 C26 108.5(2) . . ? N3 C25 C24 113.5(2) . . ? C26 C25 C24 108.4(2) . . ? N3 C25 H25 108.8 . . ? C26 C25 H25 108.8 . . ? C24 C25 H25 108.8 . . ? O7 C26 C25 112.0(3) . . ? O7 C26 H26A 109.2 . . ? C25 C26 H26A 109.2 . . ? O7 C26 H26B 109.2 . . ? C25 C26 H26B 109.2 . . ? H26A C26 H26B 107.9 . . ? O10 N4 O9 123.3(5) . . ? O10 N4 C31 117.8(5) . . ? O9 N4 C31 118.8(5) . . ? O8 C27 N3 127.7(8) . . ? O8 C27 C28 119.2(12) . . ? N3 C27 C28 113.1(10) . . ? C29 C28 C33 118.0(9) . . ? C29 C28 C27 120.0(7) . . ? C33 C28 C27 122.0(10) . . ? C30 C29 C28 121.8(5) . . ? C30 C29 H29 119.1 . . ? C28 C29 H29 119.1 . . ? C29 C30 C31 118.1(5) . . ? C29 C30 H30 121.0 . . ? C31 C30 H30 121.0 . . ? C32 C31 C30 123.1(5) . . ? C32 C31 N4 118.6(6) . . ? C30 C31 N4 118.3(6) . . ? C31 C32 C33 117.5(6) . . ? C31 C32 H32 121.3 . . ? C33 C32 H32 121.3 . . ? C32 C33 C28 121.6(8) . . ? C32 C33 H33 119.2 . . ? C28 C33 H33 119.2 . . ? O10C N4A O9A 125.0(12) . . ? O10C N4A C31A 119.5(11) . . ? O9A N4A C31A 115.5(14) . . ? O8A C27A N3 114.1(16) . . ? O8A C27A C28A 124(3) . . ? N3 C27A C28A 121(2) . . ? C33A C28A C29A 120.8(15) . . ? C33A C28A C27A 123(2) . . ? C29A C28A C27A 116.1(17) . . ? C28A C29A C30A 120.2(12) . . ? C28A C29A H29A 119.9 . . ? C30A C29A H29A 119.9 . . ? C31A C30A C29A 116.8(12) . . ? C31A C30A H30A 121.6 . . ? C29A C30A H30A 121.6 . . ? C30A C31A C32A 125.3(12) . . ? C30A C31A N4A 118.0(13) . . ? C32A C31A N4A 116.4(12) . . ? C31A C32A C33A 116.6(12) . . ? C31A C32A H32A 121.7 . . ? C33A C32A H32A 121.7 . . ? C28A C33A C32A 120.1(15) . . ? C28A C33A H33A 119.9 . . ? C32A C33A H33A 119.9 . . ? O34A C35A C34 117.7(12) . . ? C341 C34 C351 138(3) . . ? C341 C34 O34B 69.1(17) . . ? C351 C34 O34B 104.3(17) . . ? C341 C34 O34 117.5(18) . . ? C351 C34 O34 46.2(14) . . ? O34B C34 O34 58.7(10) . . ? C341 C34 C35A 18.7(19) . . ? C351 C34 C35A 121.8(18) . . ? O34B C34 C35A 80.3(12) . . ? O34 C34 C35A 116.0(11) . . ? C341 C34 C35 29.9(17) . . ? C351 C34 C35 152.7(16) . . ? O34B C34 C35 52.0(11) . . ? O34 C34 C35 110.4(8) . . ? C35A C34 C35 48.6(10) . . ? C341 C34 C35B 61(2) . . ? C351 C34 C35B 161(2) . . ? O34B C34 C35B 84.1(15) . . ? O34 C34 C35B 135.7(11) . . ? C35A C34 C35B 76.0(16) . . ? C35 C34 C35B 43.7(12) . . ? C341 C34 O341 46.7(13) . . ? C351 C34 O341 128.8(16) . . ? O34B C34 O341 25.9(10) . . ? O34 C34 O341 84.4(6) . . ? C35A C34 O341 62.0(8) . . ? C35 C34 O341 26.1(5) . . ? C35B C34 O341 63.2(13) . . ? C34 C341 O341 112.1(18) . . ? C34 C341 C351 23.4(16) . . ? O341 C341 C351 115.8(15) . . ? C341 O341 C34 21.2(7) . . ? C34 C351 C341 18.8(12) . . ? 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 2.1(3) . . . . ? C22 O2 C2 C3 -177.1(2) . . . . ? C6 C1 C2 O2 179.2(2) . . . . ? C6 C1 C2 C3 -1.7(4) . . . . ? C23 O3 C3 C4 -8.6(4) . . . . ? C23 O3 C3 C2 169.8(2) . . . . ? O2 C2 C3 O3 0.6(3) . . . . ? C1 C2 C3 O3 -178.6(2) . . . . ? O2 C2 C3 C4 179.2(2) . . . . ? C1 C2 C3 C4 0.0(4) . . . . ? O3 C3 C4 C5 -180.0(2) . . . . ? C2 C3 C4 C5 1.7(4) . . . . ? C3 C4 C5 C6 -1.5(4) . . . . ? C3 C4 C5 C7 -171.2(2) . . . . ? C4 C5 C6 C1 -0.3(4) . . . . ? C7 C5 C6 C1 171.3(2) . . . . ? C4 C5 C6 N1 -179.5(2) . . . . ? C7 C5 C6 N1 -7.9(3) . . . . ? C2 C1 C6 C5 1.9(4) . . . . ? C2 C1 C6 N1 -179.1(2) . . . . ? C9 N1 C6 C5 -156.9(3) . . . . ? C8 N1 C6 C5 -3.0(3) . . . . ? C9 N1 C6 C1 23.9(4) . . . . ? C8 N1 C6 C1 177.9(2) . . . . ? C6 C5 C7 C17 -104.5(2) . . . . ? C4 C5 C7 C17 66.1(3) . . . . ? C6 C5 C7 C21 139.5(2) . . . . ? C4 C5 C7 C21 -50.0(3) . . . . ? C6 C5 C7 C8 14.6(3) . . . . ? C4 C5 C7 C8 -174.8(2) . . . . ? C9 N1 C8 C18 42.1(3) . . . . ? C6 N1 C8 C18 -113.3(2) . . . . ? C9 N1 C8 C7 167.4(2) . . . . ? C6 N1 C8 C7 12.0(3) . . . . ? C5 C7 C8 N1 -15.6(2) . . . . ? C17 C7 C8 N1 103.0(2) . . . . ? C21 C7 C8 N1 -142.8(2) . . . . ? C5 C7 C8 C18 102.5(2) . . . . ? C17 C7 C8 C18 -138.9(2) . . . . ? C21 C7 C8 C18 -24.7(3) . . . . ? C6 N1 C9 O4 -20.0(4) . . . . ? C8 N1 C9 O4 -171.4(3) . . . . ? C6 N1 C9 C10 160.9(3) . . . . ? C8 N1 C9 C10 9.5(4) . . . . ? O4 C9 C10 C11 146.7(3) . . . . ? N1 C9 C10 C11 -34.2(4) . . . . ? C12 O1 C11 C18 -69.0(3) . . . . ? C12 O1 C11 C10 169.9(2) . . . . ? C9 C10 C11 O1 126.7(3) . . . . ? C9 C10 C11 C18 3.6(4) . . . . ? C11 O1 C12 C13 89.2(3) . . . . ? O1 C12 C13 C14 -64.9(4) . . . . ? C12 C13 C14 C15 178.0(3) . . . . ? C12 C13 C14 C19 -1.6(4) . . . . ? C13 C14 C15 N2 -124.6(3) . . . . ? C19 C14 C15 N2 54.9(3) . . . . ? C16 N2 C15 C14 74.5(3) . . . . ? C21 N2 C15 C14 -47.0(3) . . . . ? C15 N2 C16 C17 -142.5(2) . . . . ? C21 N2 C16 C17 -17.9(3) . . . . ? N2 C16 C17 C7 37.5(3) . . . . ? C5 C7 C17 C16 -167.3(2) . . . . ? C21 C7 C17 C16 -42.1(2) . . . . ? C8 C7 C17 C16 79.1(2) . . . . ? O1 C11 C18 C19 57.2(3) . . . . ? C10 C11 C18 C19 175.2(2) . . . . ? O1 C11 C18 C8 -71.3(3) . . . . ? C10 C11 C18 C8 46.6(3) . . . . ? N1 C8 C18 C19 157.9(2) . . . . ? C7 C8 C18 C19 40.8(3) . . . . ? N1 C8 C18 C11 -70.6(3) . . . . ? C7 C8 C18 C11 172.4(2) . . . . ? C13 C14 C19 C18 57.8(3) . . . . ? C15 C14 C19 C18 -121.7(2) . . . . ? C13 C14 C19 C20 176.3(2) . . . . ? C15 C14 C19 C20 -3.3(3) . . . . ? C11 C18 C19 C14 -67.2(3) . . . . ? C8 C18 C19 C14 58.7(3) . . . . ? C11 C18 C19 C20 172.6(2) . . . . ? C8 C18 C19 C20 -61.5(3) . . . . ? C14 C19 C20 C21 -55.4(3) . . . . ? C18 C19 C20 C21 68.7(2) . . . . ? C19 C20 C21 N2 62.9(3) . . . . ? C19 C20 C21 C7 -56.1(3) . . . . ? C16 N2 C21 C20 -133.9(2) . . . . ? C15 N2 C21 C20 -10.0(3) . . . . ? C16 N2 C21 C7 -8.3(2) . . . . ? C15 N2 C21 C7 115.7(2) . . . . ? C5 C7 C21 C20 -86.6(3) . . . . ? C17 C7 C21 C20 152.6(2) . . . . ? C8 C7 C21 C20 32.7(3) . . . . ? C5 C7 C21 N2 151.47(19) . . . . ? C17 C7 C21 N2 30.6(2) . . . . ? C8 C7 C21 N2 -89.3(2) . . . . ? C27 N3 C25 C26 162.9(7) . . . . ? C27A N3 C25 C26 155.3(18) . . . . ? C27 N3 C25 C24 -76.5(8) . . . . ? C27A N3 C25 C24 -84.1(18) . . . . ? O6 C24 C25 N3 -18.4(4) . . . . ? O5 C24 C25 N3 166.1(2) . . . . ? O6 C24 C25 C26 102.2(3) . . . . ? O5 C24 C25 C26 -73.3(3) . . . . ? N3 C25 C26 O7 -65.9(3) . . . . ? C24 C25 C26 O7 170.5(2) . . . . ? C27A N3 C27 O8 165(8) . . . . ? C25 N3 C27 O8 4.7(18) . . . . ? C27A N3 C27 C28 -19(6) . . . . ? C25 N3 C27 C28 -178.8(7) . . . . ? O8 C27 C28 C29 27.1(19) . . . . ? N3 C27 C28 C29 -149.7(10) . . . . ? O8 C27 C28 C33 -152.9(12) . . . . ? N3 C27 C28 C33 30.2(17) . . . . ? C33 C28 C29 C30 -2.2(14) . . . . ? C27 C28 C29 C30 177.8(10) . . . . ? C28 C29 C30 C31 1.6(11) . . . . ? C29 C30 C31 C32 -0.5(10) . . . . ? C29 C30 C31 N4 179.3(5) . . . . ? O10 N4 C31 C32 -14.8(9) . . . . ? O9 N4 C31 C32 168.2(5) . . . . ? O10 N4 C31 C30 165.4(6) . . . . ? O9 N4 C31 C30 -11.7(8) . . . . ? C30 C31 C32 C33 0.1(10) . . . . ? N4 C31 C32 C33 -179.8(7) . . . . ? C31 C32 C33 C28 -0.6(13) . . . . ? C29 C28 C33 C32 1.7(16) . . . . ? C27 C28 C33 C32 -178.3(11) . . . . ? C27 N3 C27A O8A -25(5) . . . . ? C25 N3 C27A O8A 0(3) . . . . ? C27 N3 C27A C28A 164(9) . . . . ? C25 N3 C27A C28A -171.1(15) . . . . ? O8A C27A C28A C33A -129(3) . . . . ? N3 C27A C28A C33A 41(4) . . . . ? O8A C27A C28A C29A 45(4) . . . . ? N3 C27A C28A C29A -145(2) . . . . ? C33A C28A C29A C30A -4(3) . . . . ? C27A C28A C29A C30A -179(2) . . . . ? C28A C29A C30A C31A 3(2) . . . . ? C29A C30A C31A C32A 0(2) . . . . ? C29A C30A C31A N4A 173.3(11) . . . . ? O10C N4A C31A C30A -167.6(12) . . . . ? O9A N4A C31A C30A 14.2(16) . . . . ? O10C N4A C31A C32A 6.4(17) . . . . ? O9A N4A C31A C32A -171.9(11) . . . . ? C30A C31A C32A C33A -2(2) . . . . ? N4A C31A C32A C33A -175.5(14) . . . . ? C29A C28A C33A C32A 2(3) . . . . ? C27A C28A C33A C32A 176(2) . . . . ? C31A C32A C33A C28A 1(3) . . . . ? O34A C35A C34 C341 39(5) . . . . ? O34A C35A C34 C351 -114(2) . . . . ? O34A C35A C34 O34B -13(2) . . . . ? O34A C35A C34 O34 -61(2) . . . . ? O34A C35A C34 C35 34.3(14) . . . . ? O34A C35A C34 C35B 74(2) . . . . ? O34A C35A C34 O341 6.7(15) . . . . ? C351 C34 C341 O341 -104(3) . . . . ? O34B C34 C341 O341 -15.6(15) . . . . ? O34 C34 C341 O341 -50(3) . . . . ? C35A C34 C341 O341 -140(7) . . . . ? C35 C34 C341 O341 33.3(16) . . . . ? C35B C34 C341 O341 79(2) . . . . ? O34B C34 C341 C351 88(3) . . . . ? O34 C34 C341 C351 54(3) . . . . ? C35A C34 C341 C351 -36(7) . . . . ? C35 C34 C341 C351 137(4) . . . . ? C35B C34 C341 C351 -177(3) . . . . ? O341 C34 C341 C351 104(3) . . . . ? C351 C341 O341 C34 -25.4(17) . . . . ? C351 C34 O341 C341 123(4) . . . . ? O34B C34 O341 C341 145(4) . . . . ? O34 C34 O341 C341 137(3) . . . . ? C35A C34 O341 C341 13(3) . . . . ? C35 C34 O341 C341 -38(3) . . . . ? C35B C34 O341 C341 -74(3) . . . . ? O34B C34 C351 C341 -74(3) . . . . ? O34 C34 C351 C341 -84(3) . . . . ? C35A C34 C351 C341 13(2) . . . . ? C35 C34 C351 C341 -47(3) . . . . ? C35B C34 C351 C341 171(8) . . . . ? O341 C34 C351 C341 -65(3) . . . . ? O341 C341 C351 C34 86(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 H2A O5 0.91 1.77 2.667(3) 168.2 . O7 H7 O6 0.82 1.87 2.685(3) 170.4 3_656 N3 H3 O5 0.86 2.01 2.837(3) 160.2 3_656 _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.293 _refine_diff_density_min -0.174 _refine_diff_density_rms 0.042 # start Validation Reply Form _vrf_PLAT432_12 ; PROBLEM: Short Inter X...Y Contact C34 .. O34B .. 1.44 Ang. RESPONSE: ethanol molecule is disordered over many positions ; # end Validation Reply Form #==== end of cif