# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_coden_Cambridge 1350 _journal_volume ? _journal_page_first ? _journal_year ? loop_ _publ_author_name 'Ren-Gen Xiong.' 'De-Hong Wu.' 'Jia-Zhen Ge.' 'Hong-Ling Cai.' 'Wen Zhang.' _publ_contact_author_name 'Ren-Gen Xiong' _publ_contact_author_email xiongrg@seu.edu.cn _publ_section_title ; Organic salt of hydrogen L-tartaric acid: a novel wide-temperature-range ferroelectrics with a reversible phase transition ; # Attachment '- 1.cif' data_wudh_LTP(93K) _database_code_depnum_ccdc_archive 'CCDC 773837' #TrackingRef '- 1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C8 H12 N, C4 H5 O6' _chemical_formula_sum 'C12 H17 N O6' _chemical_formula_weight 271.27 _chemical_absolute_configuration syn 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 triclinic _symmetry_space_group_name_H-M 'P 1' _symmetry_space_group_name_Hall 'P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' _cell_length_a 7.4649(16) _cell_length_b 11.9022(18) _cell_length_c 14.8739(11) _cell_angle_alpha 95.276(2) _cell_angle_beta 91.966(2) _cell_angle_gamma 107.856(3) _cell_volume 1249.8(3) _cell_formula_units_Z 4 _cell_measurement_temperature 93(2) _cell_measurement_reflns_used 3613 _cell_measurement_theta_min 2.7566 _cell_measurement_theta_max 27.4700 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.442 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 576 _exptl_absorpt_coefficient_mu 0.116 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.962 _exptl_absorpt_correction_T_max 0.970 _exptl_absorpt_process_details 'CrystalClear (Rigaku, 2005)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 93(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 'Mercury2 (2x2 bin mode)' _diffrn_measurement_method CCD_Profile_fitting _diffrn_detector_area_resol_mean 13.6612 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10388 _diffrn_reflns_av_R_equivalents 0.0232 _diffrn_reflns_av_sigmaI/netI 0.0412 _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 -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.76 _diffrn_reflns_theta_max 27.49 _reflns_number_total 5593 _reflns_number_gt 4617 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku, 2005)' _computing_cell_refinement CrystalClear _computing_data_reduction CrystalClear _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material SHELXTL _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^)+(0.0323P)^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 ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 10(10) _refine_ls_number_reflns 5593 _refine_ls_number_parameters 705 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0450 _refine_ls_R_factor_gt 0.0362 _refine_ls_wR_factor_ref 0.0759 _refine_ls_wR_factor_gt 0.0725 _refine_ls_goodness_of_fit_ref 1.081 _refine_ls_restrained_S_all 1.081 _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 C1 C 0.7926(4) 0.1666(3) 0.51988(19) 0.0231(7) Uani 1 1 d . . . H1A H 0.8947 0.2226 0.4945 0.035 Uiso 1 1 calc R . . H1B H 0.8203 0.1694 0.5837 0.035 Uiso 1 1 calc R . . H1C H 0.6786 0.1863 0.5098 0.035 Uiso 1 1 calc R . . C2 C 0.7677(4) 0.0424(3) 0.47485(18) 0.0191(7) Uani 1 1 d . . . H2A H 0.6597 -0.0124 0.4987 0.023 Uiso 1 1 calc R . . H2B H 0.8779 0.0203 0.4916 0.023 Uiso 1 1 calc R . . C3 C 0.7394(4) 0.0273(3) 0.37206(19) 0.0149(6) Uani 1 1 d . . . C4 C 0.7149(4) -0.0837(2) 0.32471(19) 0.0164(6) Uani 1 1 d . . . H4 H 0.7138 -0.1474 0.3567 0.020 Uiso 1 1 calc R . . C5 C 0.6919(4) -0.1012(3) 0.23056(19) 0.0153(6) Uani 1 1 d . . . H5 H 0.6753 -0.1758 0.1999 0.018 Uiso 1 1 calc R . . C6 C 0.6941(4) -0.0058(2) 0.18330(18) 0.0115(6) Uani 1 1 d . . . C7 C 0.7187(4) 0.1054(2) 0.22851(18) 0.0134(6) Uani 1 1 d . . . H7 H 0.7204 0.1691 0.1963 0.016 Uiso 1 1 calc R . . C8 C 0.7408(4) 0.1212(3) 0.32298(19) 0.0151(6) Uani 1 1 d . . . H8 H 0.7567 0.1958 0.3534 0.018 Uiso 1 1 calc R . . C9 C 0.2151(5) -0.0693(3) 0.2693(2) 0.0273(7) Uani 1 1 d . . . H9A H 0.3210 -0.0906 0.2917 0.041 Uiso 1 1 calc R . . H9B H 0.2142 -0.0719 0.2046 0.041 Uiso 1 1 calc R . . H9C H 0.1005 -0.1242 0.2860 0.041 Uiso 1 1 calc R . . C10 C 0.2302(4) 0.0550(3) 0.30969(18) 0.0216(7) Uani 1 1 d . . . H10A H 0.1177 0.0728 0.2900 0.026 Uiso 1 1 calc R . . H10B H 0.3369 0.1105 0.2855 0.026 Uiso 1 1 calc R . . C11 C 0.2538(4) 0.0759(3) 0.41240(19) 0.0151(6) Uani 1 1 d . . . C12 C 0.2796(4) 0.1890(3) 0.45507(19) 0.0178(6) Uani 1 1 d . . . H12 H 0.2840 0.2505 0.4200 0.021 Uiso 1 1 calc R . . C13 C 0.2990(4) 0.2127(2) 0.54900(18) 0.0145(6) Uani 1 1 d . . . H13 H 0.3142 0.2888 0.5764 0.017 Uiso 1 1 calc R . . C14 C 0.2953(4) 0.1216(2) 0.60070(18) 0.0121(6) Uani 1 1 d . . . C15 C 0.2728(4) 0.0083(2) 0.56064(19) 0.0151(6) Uani 1 1 d . . . H15 H 0.2715 -0.0526 0.5958 0.018 Uiso 1 1 calc R . . C16 C 0.2523(4) -0.0130(3) 0.46661(19) 0.0164(6) Uani 1 1 d . . . H16 H 0.2370 -0.0891 0.4394 0.020 Uiso 1 1 calc R . . C17 C 0.3541(4) 0.6712(3) 0.52004(19) 0.0226(7) Uani 1 1 d . . . H17A H 0.4746 0.6928 0.4943 0.034 Uiso 1 1 calc R . . H17B H 0.3718 0.6694 0.5841 0.034 Uiso 1 1 calc R . . H17C H 0.2915 0.7285 0.5090 0.034 Uiso 1 1 calc R . . C18 C 0.2341(4) 0.5487(3) 0.47671(18) 0.0177(6) Uani 1 1 d . . . H18A H 0.2885 0.4902 0.4965 0.021 Uiso 1 1 calc R . . H18B H 0.1089 0.5316 0.4990 0.021 Uiso 1 1 calc R . . C19 C 0.2146(4) 0.5340(3) 0.37374(18) 0.0142(6) Uani 1 1 d . . . C20 C 0.1277(4) 0.4219(2) 0.32849(18) 0.0155(6) Uani 1 1 d . . . H20 H 0.0817 0.3581 0.3620 0.019 Uiso 1 1 calc R . . C21 C 0.1072(4) 0.4020(2) 0.23416(19) 0.0153(6) Uani 1 1 d . . . H21 H 0.0496 0.3261 0.2051 0.018 Uiso 1 1 calc R . . C22 C 0.1744(4) 0.4979(2) 0.18460(17) 0.0117(6) Uani 1 1 d . . . C23 C 0.2595(4) 0.6112(2) 0.22777(18) 0.0145(6) Uani 1 1 d . . . H23 H 0.3020 0.6752 0.1942 0.017 Uiso 1 1 calc R . . C24 C 0.2809(4) 0.6283(3) 0.32246(18) 0.0154(6) Uani 1 1 d . . . H24 H 0.3405 0.7040 0.3514 0.018 Uiso 1 1 calc R . . C25 C 0.6340(5) 0.4241(3) 0.2734(2) 0.0284(8) Uani 1 1 d . . . H25A H 0.6916 0.3699 0.2967 0.043 Uiso 1 1 calc R . . H25B H 0.6363 0.4180 0.2087 0.043 Uiso 1 1 calc R . . H25C H 0.5057 0.4047 0.2900 0.043 Uiso 1 1 calc R . . C26 C 0.7412(4) 0.5490(3) 0.31256(18) 0.0215(7) Uani 1 1 d . . . H26A H 0.6787 0.6021 0.2898 0.026 Uiso 1 1 calc R . . H26B H 0.8665 0.5698 0.2902 0.026 Uiso 1 1 calc R . . C27 C 0.7617(4) 0.5719(3) 0.41579(19) 0.0168(6) Uani 1 1 d . . . C28 C 0.8568(4) 0.6853(3) 0.45711(19) 0.0186(6) Uani 1 1 d . . . H28 H 0.9089 0.7456 0.4213 0.022 Uiso 1 1 calc R . . C29 C 0.8757(4) 0.7106(2) 0.55038(19) 0.0166(6) Uani 1 1 d . . . H29 H 0.9391 0.7871 0.5769 0.020 Uiso 1 1 calc R . . C30 C 0.7990(4) 0.6203(2) 0.60331(18) 0.0123(6) Uani 1 1 d . . . C31 C 0.7096(4) 0.5063(2) 0.56440(19) 0.0150(6) Uani 1 1 d . . . H31 H 0.6628 0.4455 0.6006 0.018 Uiso 1 1 calc R . . C32 C 0.6897(4) 0.4826(3) 0.4710(2) 0.0186(7) Uani 1 1 d . . . H32 H 0.6273 0.4058 0.4448 0.022 Uiso 1 1 calc R . . C33 C 0.6678(4) 0.2735(2) -0.00260(17) 0.0109(5) Uani 1 1 d . . . C34 C 0.4601(3) 0.2692(2) -0.01664(17) 0.0110(5) Uani 1 1 d . . . H34 H 0.4300 0.2713 -0.0810 0.013 Uiso 1 1 calc R . . C35 C 0.3294(4) 0.1559(2) 0.01458(18) 0.0125(5) Uani 1 1 d . . . H35 H 0.3249 0.0888 -0.0298 0.015 Uiso 1 1 calc R . . C36 C 0.1315(4) 0.1630(2) 0.02283(17) 0.0107(5) Uani 1 1 d . . . C37 C 1.1867(4) 0.7733(2) -0.00396(18) 0.0133(6) Uani 1 1 d . . . C38 C 0.9796(3) 0.7715(2) -0.01731(17) 0.0105(5) Uani 1 1 d . . . H38 H 0.9491 0.7749 -0.0814 0.013 Uiso 1 1 calc R . . C39 C 0.8498(4) 0.6563(2) 0.01318(17) 0.0127(6) Uani 1 1 d . . . H39 H 0.8475 0.5897 -0.0314 0.015 Uiso 1 1 calc R . . C40 C 0.6506(4) 0.6605(2) 0.02152(18) 0.0119(6) Uani 1 1 d . . . C41 C 0.3565(4) 0.4677(2) 0.75071(17) 0.0108(5) Uani 1 1 d . . . C42 C 0.1422(3) 0.4379(2) 0.73262(18) 0.0100(5) Uani 1 1 d . . . H42 H 0.1014 0.3810 0.6783 0.012 Uiso 1 1 calc R . . C43 C 0.0387(3) 0.3822(2) 0.81306(17) 0.0102(5) Uani 1 1 d . . . H43 H 0.0593 0.3053 0.8169 0.012 Uiso 1 1 calc R . . C44 C -0.1722(4) 0.3598(2) 0.78958(17) 0.0110(5) Uani 1 1 d . . . C45 C 0.8603(4) 0.9676(2) 0.75006(17) 0.0117(6) Uani 1 1 d . . . C46 C 0.6468(3) 0.9368(2) 0.73183(18) 0.0118(5) Uani 1 1 d . . . H46 H 0.6069 0.8799 0.6775 0.014 Uiso 1 1 calc R . . C47 C 0.5415(4) 0.8807(2) 0.81243(17) 0.0109(5) Uani 1 1 d . . . H47 H 0.5610 0.8034 0.8164 0.013 Uiso 1 1 calc R . . C48 C 0.3327(4) 0.8599(2) 0.78777(17) 0.0111(6) Uani 1 1 d . . . N1 N 0.6674(3) -0.0234(2) 0.08424(14) 0.0130(5) Uani 1 1 d . . . H1D H 0.7512 -0.0559 0.0618 0.020 Uiso 1 1 calc R . . H1E H 0.6834 0.0463 0.0631 0.020 Uiso 1 1 calc R . . H1F H 0.5513 -0.0713 0.0678 0.020 Uiso 1 1 calc R . . N2 N 0.3146(3) 0.14375(19) 0.69966(14) 0.0111(5) Uani 1 1 d . . . H2C H 0.3543 0.2216 0.7161 0.017 Uiso 1 1 calc R . . H2D H 0.3979 0.1113 0.7211 0.017 Uiso 1 1 calc R . . H2E H 0.2034 0.1117 0.7219 0.017 Uiso 1 1 calc R . . N3 N 0.8160(3) 0.6445(2) 0.70213(14) 0.0121(5) Uani 1 1 d . . . H3A H 0.7032 0.6159 0.7238 0.018 Uiso 1 1 calc R . . H3B H 0.8605 0.7225 0.7177 0.018 Uiso 1 1 calc R . . H3C H 0.8947 0.6098 0.7249 0.018 Uiso 1 1 calc R . . N4 N 0.1543(3) 0.4778(2) 0.08564(14) 0.0121(5) Uani 1 1 d . . . H4A H 0.2385 0.4439 0.0657 0.018 Uiso 1 1 calc R . . H4B H 0.1737 0.5470 0.0631 0.018 Uiso 1 1 calc R . . H4C H 0.0385 0.4304 0.0680 0.018 Uiso 1 1 calc R . . O1 O 0.7125(3) 0.18781(16) -0.04199(13) 0.0169(5) Uani 1 1 d . . . O2 O 0.7739(3) 0.35920(16) 0.04782(12) 0.0148(4) Uani 1 1 d . . . O3 O 0.4347(2) 0.37039(15) 0.03398(13) 0.0155(4) Uani 1 1 d . . . H3 H 0.5329 0.4079 0.0636 0.023 Uiso 1 1 calc R . . O4 O 0.4009(3) 0.13662(17) 0.09951(12) 0.0178(4) Uani 1 1 d . . . H4D H 0.3188 0.1287 0.1358 0.027 Uiso 1 1 calc R . . O5 O 0.0566(2) 0.18522(17) -0.05147(12) 0.0158(4) Uani 1 1 d . . . H5A H -0.0450 0.1953 -0.0415 0.024 Uiso 1 1 calc R . . O6 O 0.0562(3) 0.15034(16) 0.09441(12) 0.0190(4) Uani 1 1 d . . . O7 O 1.2302(3) 0.68915(17) -0.04563(13) 0.0181(5) Uani 1 1 d . . . O8 O 1.2926(3) 0.85787(16) 0.04745(13) 0.0159(4) Uani 1 1 d . . . O9 O 0.9547(2) 0.87134(15) 0.03506(12) 0.0149(4) Uani 1 1 d . . . H9 H 1.0505 0.9053 0.0676 0.022 Uiso 1 1 calc R . . O10 O 0.9235(3) 0.63813(17) 0.09807(12) 0.0163(4) Uani 1 1 d . . . H10 H 0.8380 0.6197 0.1323 0.024 Uiso 1 1 calc R . . O11 O 0.5773(2) 0.68887(17) -0.05064(12) 0.0173(4) Uani 1 1 d . . . H11 H 0.4690 0.6881 -0.0423 0.026 Uiso 1 1 calc R . . O12 O 0.5696(3) 0.63732(16) 0.09085(12) 0.0194(5) Uani 1 1 d . . . O13 O 0.4530(2) 0.57215(15) 0.74714(12) 0.0144(4) Uani 1 1 d . . . O14 O 0.4174(2) 0.38270(15) 0.76634(12) 0.0150(4) Uani 1 1 d . . . O15 O 0.0963(2) 0.54134(15) 0.71836(13) 0.0137(4) Uani 1 1 d . . . H15A H 0.1922 0.5988 0.7251 0.021 Uiso 1 1 calc R . . O16 O 0.1069(2) 0.45306(15) 0.89547(11) 0.0134(4) Uani 1 1 d . . . H16A H 0.1110 0.5217 0.8900 0.020 Uiso 1 1 calc R . . O17 O -0.2428(3) 0.43697(16) 0.83117(13) 0.0135(4) Uani 1 1 d . . . H17 H -0.3547 0.4205 0.8148 0.020 Uiso 1 1 calc R . . O18 O -0.2600(3) 0.27975(16) 0.73294(12) 0.0145(4) Uani 1 1 d . . . O19 O 0.9564(2) 1.07244(15) 0.74521(12) 0.0148(4) Uani 1 1 d . . . O20 O 0.9225(2) 0.88360(15) 0.76718(13) 0.0155(4) Uani 1 1 d . . . O21 O 0.5987(2) 1.03966(16) 0.71748(13) 0.0148(4) Uani 1 1 d . . . H21A H 0.6943 1.0973 0.7228 0.022 Uiso 1 1 calc R . . O22 O 0.6108(2) 0.95199(15) 0.89428(11) 0.0130(4) Uani 1 1 d . . . H22 H 0.6048 1.0190 0.8902 0.020 Uiso 1 1 calc R . . O23 O 0.2610(3) 0.93510(16) 0.83135(13) 0.0150(4) Uani 1 1 d . . . H23A H 0.1511 0.9216 0.8125 0.022 Uiso 1 1 calc R . . O24 O 0.2466(3) 0.78215(16) 0.72876(12) 0.0147(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0178(15) 0.0398(19) 0.0113(14) 0.0014(13) 0.0009(12) 0.0088(14) C2 0.0152(14) 0.0308(17) 0.0108(13) 0.0037(12) 0.0006(11) 0.0060(13) C3 0.0101(13) 0.0206(15) 0.0138(14) 0.0023(11) -0.0004(11) 0.0047(12) C4 0.0146(14) 0.0166(14) 0.0183(14) 0.0049(11) -0.0008(12) 0.0048(12) C5 0.0119(13) 0.0152(14) 0.0195(15) -0.0008(11) 0.0009(11) 0.0058(11) C6 0.0094(13) 0.0139(14) 0.0108(13) 0.0019(10) -0.0001(11) 0.0030(11) C7 0.0124(14) 0.0131(14) 0.0139(14) 0.0017(11) -0.0017(11) 0.0029(11) C8 0.0104(14) 0.0164(15) 0.0169(14) -0.0061(11) -0.0024(11) 0.0045(11) C9 0.0250(17) 0.044(2) 0.0157(15) -0.0021(14) 0.0014(13) 0.0161(15) C10 0.0156(15) 0.0347(18) 0.0153(15) 0.0042(13) 0.0007(12) 0.0088(14) C11 0.0072(13) 0.0241(16) 0.0135(14) 0.0032(11) 0.0011(11) 0.0039(12) C12 0.0153(15) 0.0236(16) 0.0184(15) 0.0106(12) 0.0046(12) 0.0089(12) C13 0.0139(14) 0.0119(13) 0.0187(14) 0.0034(11) 0.0021(11) 0.0046(11) C14 0.0060(12) 0.0153(14) 0.0154(14) 0.0012(11) -0.0001(11) 0.0043(11) C15 0.0119(14) 0.0155(14) 0.0184(14) 0.0051(11) 0.0010(11) 0.0044(11) C16 0.0163(15) 0.0152(15) 0.0186(15) 0.0026(11) 0.0019(12) 0.0059(12) C17 0.0201(16) 0.0338(18) 0.0138(14) -0.0038(13) -0.0008(12) 0.0101(14) C18 0.0150(14) 0.0277(17) 0.0127(14) 0.0020(12) 0.0004(12) 0.0099(13) C19 0.0097(13) 0.0234(16) 0.0096(13) 0.0018(11) 0.0004(11) 0.0056(12) C20 0.0158(14) 0.0158(14) 0.0161(14) 0.0058(11) 0.0009(11) 0.0056(11) C21 0.0157(14) 0.0124(14) 0.0175(14) 0.0003(11) -0.0010(11) 0.0046(11) C22 0.0067(12) 0.0185(15) 0.0111(13) -0.0013(11) -0.0006(10) 0.0064(11) C23 0.0148(14) 0.0151(14) 0.0132(14) 0.0034(11) 0.0038(11) 0.0031(11) C24 0.0144(14) 0.0175(15) 0.0122(13) -0.0017(11) -0.0010(11) 0.0032(12) C25 0.0248(17) 0.049(2) 0.0125(15) -0.0014(14) -0.0025(13) 0.0148(16) C26 0.0181(15) 0.0365(19) 0.0157(15) 0.0084(13) 0.0047(12) 0.0149(14) C27 0.0125(14) 0.0254(17) 0.0166(14) 0.0066(12) 0.0013(11) 0.0106(12) C28 0.0141(14) 0.0223(16) 0.0225(15) 0.0117(12) 0.0042(12) 0.0073(12) C29 0.0114(13) 0.0145(14) 0.0232(15) 0.0014(12) 0.0009(12) 0.0033(11) C30 0.0084(13) 0.0167(15) 0.0119(13) 0.0049(11) -0.0018(11) 0.0033(11) C31 0.0129(14) 0.0145(14) 0.0167(14) 0.0053(11) 0.0014(11) 0.0017(11) C32 0.0150(15) 0.0181(16) 0.0222(16) 0.0006(12) 0.0020(12) 0.0048(12) C33 0.0102(13) 0.0117(13) 0.0112(13) 0.0042(10) -0.0003(10) 0.0030(10) C34 0.0083(12) 0.0127(13) 0.0125(13) -0.0017(10) 0.0007(10) 0.0047(10) C35 0.0124(13) 0.0116(13) 0.0142(13) 0.0025(10) -0.0009(10) 0.0048(10) C36 0.0098(13) 0.0073(12) 0.0131(13) -0.0012(10) -0.0005(10) 0.0007(10) C37 0.0103(13) 0.0178(15) 0.0122(13) 0.0052(11) 0.0014(10) 0.0037(11) C38 0.0108(13) 0.0099(13) 0.0103(12) 0.0005(10) -0.0004(10) 0.0029(10) C39 0.0139(13) 0.0140(14) 0.0109(13) 0.0006(10) 0.0001(10) 0.0057(11) C40 0.0119(13) 0.0067(13) 0.0146(13) -0.0013(10) -0.0002(11) 0.0000(10) C41 0.0078(12) 0.0158(14) 0.0085(13) -0.0002(10) 0.0019(10) 0.0035(11) C42 0.0058(11) 0.0094(13) 0.0152(13) 0.0008(10) 0.0006(10) 0.0027(9) C43 0.0071(12) 0.0108(13) 0.0118(13) -0.0001(10) -0.0012(10) 0.0024(10) C44 0.0091(12) 0.0112(14) 0.0142(13) 0.0040(11) 0.0010(10) 0.0046(10) C45 0.0098(13) 0.0164(14) 0.0086(13) 0.0002(10) 0.0022(10) 0.0038(11) C46 0.0094(12) 0.0125(13) 0.0146(13) 0.0028(10) 0.0006(10) 0.0045(10) C47 0.0115(13) 0.0111(13) 0.0112(13) 0.0001(10) -0.0007(10) 0.0056(10) C48 0.0100(13) 0.0086(13) 0.0161(14) 0.0068(11) 0.0049(11) 0.0029(10) N1 0.0094(11) 0.0176(13) 0.0109(11) 0.0008(9) -0.0004(9) 0.0028(10) N2 0.0094(11) 0.0111(12) 0.0131(11) 0.0013(9) 0.0015(9) 0.0036(9) N3 0.0097(11) 0.0107(12) 0.0162(12) 0.0023(9) 0.0001(9) 0.0035(9) N4 0.0103(11) 0.0158(12) 0.0102(11) -0.0020(9) 0.0001(9) 0.0052(9) O1 0.0107(10) 0.0152(10) 0.0251(11) -0.0050(9) 0.0003(8) 0.0067(8) O2 0.0109(9) 0.0174(10) 0.0147(10) -0.0020(8) 0.0006(8) 0.0034(8) O3 0.0115(9) 0.0129(10) 0.0219(10) -0.0021(8) -0.0006(8) 0.0050(8) O4 0.0182(10) 0.0220(11) 0.0146(10) 0.0065(8) -0.0019(8) 0.0075(9) O5 0.0097(9) 0.0229(11) 0.0164(10) 0.0039(8) 0.0014(8) 0.0070(8) O6 0.0143(10) 0.0216(11) 0.0190(10) 0.0012(8) 0.0049(8) 0.0023(8) O7 0.0105(10) 0.0169(11) 0.0273(12) -0.0056(9) 0.0007(9) 0.0072(8) O8 0.0112(10) 0.0169(10) 0.0171(10) -0.0043(8) 0.0001(8) 0.0024(8) O9 0.0123(9) 0.0126(9) 0.0208(10) -0.0016(8) -0.0013(8) 0.0064(8) O10 0.0169(10) 0.0183(10) 0.0159(10) 0.0060(8) 0.0002(8) 0.0075(8) O11 0.0097(9) 0.0256(11) 0.0198(10) 0.0057(8) 0.0014(8) 0.0093(8) O12 0.0147(10) 0.0263(12) 0.0159(10) 0.0036(8) 0.0032(8) 0.0041(8) O13 0.0078(8) 0.0136(10) 0.0217(10) 0.0029(8) 0.0022(7) 0.0028(7) O14 0.0096(9) 0.0143(10) 0.0222(10) -0.0004(8) -0.0004(7) 0.0059(7) O15 0.0093(9) 0.0115(9) 0.0219(10) 0.0069(8) 0.0020(8) 0.0038(7) O16 0.0149(9) 0.0132(9) 0.0121(9) 0.0005(7) -0.0017(7) 0.0050(8) O17 0.0086(9) 0.0170(10) 0.0158(10) -0.0020(8) -0.0012(8) 0.0064(8) O18 0.0097(9) 0.0156(10) 0.0162(10) -0.0040(8) -0.0023(8) 0.0031(8) O19 0.0085(9) 0.0155(10) 0.0199(10) 0.0030(8) 0.0014(7) 0.0027(7) O20 0.0098(9) 0.0129(10) 0.0246(10) -0.0001(8) -0.0019(8) 0.0056(7) O21 0.0095(9) 0.0126(10) 0.0229(10) 0.0076(8) 0.0004(8) 0.0030(7) O22 0.0146(9) 0.0139(10) 0.0103(9) 0.0003(7) -0.0017(7) 0.0044(8) O23 0.0092(9) 0.0167(11) 0.0191(10) -0.0022(8) -0.0005(8) 0.0054(8) O24 0.0113(9) 0.0146(10) 0.0166(10) -0.0019(8) -0.0026(8) 0.0032(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 C1 C2 1.519(4) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 C3 1.523(4) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C8 1.388(4) . ? C3 C4 1.395(4) . ? C4 C5 1.394(4) . ? C4 H4 0.9300 . ? C5 C6 1.386(4) . ? C5 H5 0.9300 . ? C6 C7 1.385(4) . ? C6 N1 1.467(3) . ? C7 C8 1.398(4) . ? C7 H7 0.9300 . ? C8 H8 0.9300 . ? C9 C10 1.514(4) . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 C11 1.520(4) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C16 1.385(4) . ? C11 C12 1.389(4) . ? C12 C13 1.393(4) . ? C12 H12 0.9300 . ? C13 C14 1.381(4) . ? C13 H13 0.9300 . ? C14 C15 1.381(4) . ? C14 N2 1.465(3) . ? C15 C16 1.393(4) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? C17 C18 1.527(4) . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 C19 1.522(4) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 C20 1.389(4) . ? C19 C24 1.389(4) . ? C20 C21 1.396(4) . ? C20 H20 0.9300 . ? C21 C22 1.388(4) . ? C21 H21 0.9300 . ? C22 C23 1.386(4) . ? C22 N4 1.464(3) . ? C23 C24 1.401(4) . ? C23 H23 0.9300 . ? C24 H24 0.9300 . ? C25 C26 1.507(4) . ? C25 H25A 0.9600 . ? C25 H25B 0.9600 . ? C25 H25C 0.9600 . ? C26 C27 1.529(4) . ? C26 H26A 0.9700 . ? C26 H26B 0.9700 . ? C27 C28 1.390(4) . ? C27 C32 1.390(4) . ? C28 C29 1.385(4) . ? C28 H28 0.9300 . ? C29 C30 1.383(4) . ? C29 H29 0.9300 . ? C30 C31 1.377(4) . ? C30 N3 1.465(3) . ? C31 C32 1.385(4) . ? C31 H31 0.9300 . ? C32 H32 0.9300 . ? C33 O2 1.247(3) . ? C33 O1 1.267(3) . ? C33 C34 1.542(4) . ? C34 O3 1.426(3) . ? C34 C35 1.525(3) . ? C34 H34 0.9800 . ? C35 O4 1.420(3) . ? C35 C36 1.514(4) . ? C35 H35 0.9800 . ? C36 O6 1.221(3) . ? C36 O5 1.306(3) . ? C37 O8 1.246(3) . ? C37 O7 1.262(3) . ? C37 C38 1.545(4) . ? C38 O9 1.424(3) . ? C38 C39 1.535(3) . ? C38 H38 0.9800 . ? C39 O10 1.421(3) . ? C39 C40 1.512(4) . ? C39 H39 0.9800 . ? C40 O12 1.224(3) . ? C40 O11 1.306(3) . ? C41 O13 1.238(3) . ? C41 O14 1.266(3) . ? C41 C42 1.538(3) . ? C42 O15 1.407(3) . ? C42 C43 1.537(3) . ? C42 H42 0.9800 . ? C43 O16 1.406(3) . ? C43 C44 1.536(3) . ? C43 H43 0.9800 . ? C44 O18 1.216(3) . ? C44 O17 1.311(3) . ? C45 O19 1.244(3) . ? C45 O20 1.266(3) . ? C45 C46 1.531(3) . ? C46 O21 1.409(3) . ? C46 C47 1.546(3) . ? C46 H46 0.9800 . ? C47 O22 1.403(3) . ? C47 C48 1.528(4) . ? C47 H47 0.9800 . ? C48 O24 1.219(3) . ? C48 O23 1.311(3) . ? N1 H1D 0.8900 . ? N1 H1E 0.8900 . ? N1 H1F 0.8900 . ? N2 H2C 0.8900 . ? N2 H2D 0.8900 . ? N2 H2E 0.8900 . ? N3 H3A 0.8900 . ? N3 H3B 0.8900 . ? N3 H3C 0.8900 . ? N4 H4A 0.8900 . ? N4 H4B 0.8900 . ? N4 H4C 0.8900 . ? O3 H3 0.8200 . ? O4 H4D 0.8200 . ? O5 H5A 0.8200 . ? O9 H9 0.8200 . ? O10 H10 0.8200 . ? O11 H11 0.8200 . ? O15 H15A 0.8200 . ? O16 H16A 0.8200 . ? O17 H17 0.8200 . ? O21 H21A 0.8200 . ? O22 H22 0.8200 . ? O23 H23A 0.8200 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C1 C2 C3 115.3(2) . . ? C1 C2 H2A 108.4 . . ? C3 C2 H2A 108.4 . . ? C1 C2 H2B 108.4 . . ? C3 C2 H2B 108.4 . . ? H2A C2 H2B 107.5 . . ? C8 C3 C4 118.3(3) . . ? C8 C3 C2 122.2(2) . . ? C4 C3 C2 119.5(3) . . ? C5 C4 C3 121.5(3) . . ? C5 C4 H4 119.3 . . ? C3 C4 H4 119.3 . . ? C6 C5 C4 118.9(3) . . ? C6 C5 H5 120.5 . . ? C4 C5 H5 120.5 . . ? C7 C6 C5 120.8(2) . . ? C7 C6 N1 119.7(2) . . ? C5 C6 N1 119.5(2) . . ? C6 C7 C8 119.4(3) . . ? C6 C7 H7 120.3 . . ? C8 C7 H7 120.3 . . ? C3 C8 C7 121.0(3) . . ? C3 C8 H8 119.5 . . ? C7 C8 H8 119.5 . . ? C10 C9 H9A 109.5 . . ? C10 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C10 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C9 C10 C11 115.4(3) . . ? C9 C10 H10A 108.4 . . ? C11 C10 H10A 108.4 . . ? C9 C10 H10B 108.4 . . ? C11 C10 H10B 108.4 . . ? H10A C10 H10B 107.5 . . ? C16 C11 C12 117.6(3) . . ? C16 C11 C10 123.1(3) . . ? C12 C11 C10 119.3(3) . . ? C11 C12 C13 121.7(3) . . ? C11 C12 H12 119.1 . . ? C13 C12 H12 119.1 . . ? C14 C13 C12 119.0(3) . . ? C14 C13 H13 120.5 . . ? C12 C13 H13 120.5 . . ? C13 C14 C15 121.0(3) . . ? C13 C14 N2 120.2(2) . . ? C15 C14 N2 118.8(2) . . ? C14 C15 C16 118.8(3) . . ? C14 C15 H15 120.6 . . ? C16 C15 H15 120.6 . . ? C11 C16 C15 122.0(3) . . ? C11 C16 H16 119.0 . . ? C15 C16 H16 119.0 . . ? C18 C17 H17A 109.5 . . ? C18 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C18 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C19 C18 C17 115.3(2) . . ? C19 C18 H18A 108.5 . . ? C17 C18 H18A 108.5 . . ? C19 C18 H18B 108.5 . . ? C17 C18 H18B 108.5 . . ? H18A C18 H18B 107.5 . . ? C20 C19 C24 118.1(2) . . ? C20 C19 C18 119.1(3) . . ? C24 C19 C18 122.8(2) . . ? C19 C20 C21 122.0(3) . . ? C19 C20 H20 119.0 . . ? C21 C20 H20 119.0 . . ? C22 C21 C20 118.6(2) . . ? C22 C21 H21 120.7 . . ? C20 C21 H21 120.7 . . ? C23 C22 C21 120.7(2) . . ? C23 C22 N4 120.2(2) . . ? C21 C22 N4 119.0(2) . . ? C22 C23 C24 119.4(3) . . ? C22 C23 H23 120.3 . . ? C24 C23 H23 120.3 . . ? C19 C24 C23 121.0(3) . . ? C19 C24 H24 119.5 . . ? C23 C24 H24 119.5 . . ? C26 C25 H25A 109.5 . . ? C26 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C26 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C25 C26 C27 116.1(3) . . ? C25 C26 H26A 108.3 . . ? C27 C26 H26A 108.3 . . ? C25 C26 H26B 108.3 . . ? C27 C26 H26B 108.3 . . ? H26A C26 H26B 107.4 . . ? C28 C27 C32 118.0(3) . . ? C28 C27 C26 119.6(3) . . ? C32 C27 C26 122.4(3) . . ? C29 C28 C27 121.6(3) . . ? C29 C28 H28 119.2 . . ? C27 C28 H28 119.2 . . ? C30 C29 C28 118.9(3) . . ? C30 C29 H29 120.5 . . ? C28 C29 H29 120.5 . . ? C31 C30 C29 120.8(3) . . ? C31 C30 N3 119.0(2) . . ? C29 C30 N3 120.2(2) . . ? C30 C31 C32 119.6(3) . . ? C30 C31 H31 120.2 . . ? C32 C31 H31 120.2 . . ? C31 C32 C27 121.0(3) . . ? C31 C32 H32 119.5 . . ? C27 C32 H32 119.5 . . ? O2 C33 O1 126.5(2) . . ? O2 C33 C34 116.9(2) . . ? O1 C33 C34 116.6(2) . . ? O3 C34 C35 109.8(2) . . ? O3 C34 C33 108.8(2) . . ? C35 C34 C33 110.4(2) . . ? O3 C34 H34 109.2 . . ? C35 C34 H34 109.2 . . ? C33 C34 H34 109.2 . . ? O4 C35 C36 109.4(2) . . ? O4 C35 C34 109.7(2) . . ? C36 C35 C34 111.3(2) . . ? O4 C35 H35 108.8 . . ? C36 C35 H35 108.8 . . ? C34 C35 H35 108.8 . . ? O6 C36 O5 125.4(3) . . ? O6 C36 C35 120.7(2) . . ? O5 C36 C35 113.8(2) . . ? O8 C37 O7 127.0(3) . . ? O8 C37 C38 116.1(2) . . ? O7 C37 C38 116.8(2) . . ? O9 C38 C39 109.9(2) . . ? O9 C38 C37 109.4(2) . . ? C39 C38 C37 109.1(2) . . ? O9 C38 H38 109.5 . . ? C39 C38 H38 109.5 . . ? C37 C38 H38 109.5 . . ? O10 C39 C40 109.6(2) . . ? O10 C39 C38 108.8(2) . . ? C40 C39 C38 111.7(2) . . ? O10 C39 H39 108.9 . . ? C40 C39 H39 108.9 . . ? C38 C39 H39 108.9 . . ? O12 C40 O11 124.9(3) . . ? O12 C40 C39 120.9(2) . . ? O11 C40 C39 114.2(2) . . ? O13 C41 O14 126.4(2) . . ? O13 C41 C42 116.8(2) . . ? O14 C41 C42 116.8(2) . . ? O15 C42 C43 109.5(2) . . ? O15 C42 C41 110.1(2) . . ? C43 C42 C41 110.3(2) . . ? O15 C42 H42 108.9 . . ? C43 C42 H42 108.9 . . ? C41 C42 H42 108.9 . . ? O16 C43 C44 113.9(2) . . ? O16 C43 C42 112.1(2) . . ? C44 C43 C42 106.1(2) . . ? O16 C43 H43 108.2 . . ? C44 C43 H43 108.2 . . ? C42 C43 H43 108.2 . . ? O18 C44 O17 124.2(2) . . ? O18 C44 C43 121.0(2) . . ? O17 C44 C43 114.7(2) . . ? O19 C45 O20 126.3(2) . . ? O19 C45 C46 116.8(2) . . ? O20 C45 C46 116.9(2) . . ? O21 C46 C45 110.3(2) . . ? O21 C46 C47 109.0(2) . . ? C45 C46 C47 110.8(2) . . ? O21 C46 H46 108.9 . . ? C45 C46 H46 108.9 . . ? C47 C46 H46 108.9 . . ? O22 C47 C48 114.5(2) . . ? O22 C47 C46 111.3(2) . . ? C48 C47 C46 105.5(2) . . ? O22 C47 H47 108.4 . . ? C48 C47 H47 108.4 . . ? C46 C47 H47 108.4 . . ? O24 C48 O23 124.4(2) . . ? O24 C48 C47 120.9(2) . . ? O23 C48 C47 114.6(2) . . ? C6 N1 H1D 109.5 . . ? C6 N1 H1E 109.5 . . ? H1D N1 H1E 109.5 . . ? C6 N1 H1F 109.5 . . ? H1D N1 H1F 109.5 . . ? H1E N1 H1F 109.5 . . ? C14 N2 H2C 109.5 . . ? C14 N2 H2D 109.5 . . ? H2C N2 H2D 109.5 . . ? C14 N2 H2E 109.5 . . ? H2C N2 H2E 109.5 . . ? H2D N2 H2E 109.5 . . ? C30 N3 H3A 109.5 . . ? C30 N3 H3B 109.5 . . ? H3A N3 H3B 109.5 . . ? C30 N3 H3C 109.5 . . ? H3A N3 H3C 109.5 . . ? H3B N3 H3C 109.5 . . ? C22 N4 H4A 109.5 . . ? C22 N4 H4B 109.5 . . ? H4A N4 H4B 109.5 . . ? C22 N4 H4C 109.5 . . ? H4A N4 H4C 109.5 . . ? H4B N4 H4C 109.5 . . ? C34 O3 H3 109.5 . . ? C35 O4 H4D 109.5 . . ? C36 O5 H5A 109.5 . . ? C38 O9 H9 109.5 . . ? C39 O10 H10 109.5 . . ? C40 O11 H11 109.5 . . ? C42 O15 H15A 109.5 . . ? C43 O16 H16A 109.5 . . ? C44 O17 H17 109.5 . . ? C46 O21 H21A 109.5 . . ? C47 O22 H22 109.5 . . ? C48 O23 H23A 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 C1 C2 C3 C8 1.5(4) . . . . ? C1 C2 C3 C4 -179.9(3) . . . . ? C8 C3 C4 C5 -0.1(4) . . . . ? C2 C3 C4 C5 -178.8(2) . . . . ? C3 C4 C5 C6 0.2(4) . . . . ? C4 C5 C6 C7 0.0(4) . . . . ? C4 C5 C6 N1 -179.1(2) . . . . ? C5 C6 C7 C8 -0.2(4) . . . . ? N1 C6 C7 C8 178.9(2) . . . . ? C4 C3 C8 C7 -0.1(4) . . . . ? C2 C3 C8 C7 178.6(3) . . . . ? C6 C7 C8 C3 0.3(4) . . . . ? C9 C10 C11 C16 -3.2(4) . . . . ? C9 C10 C11 C12 176.4(3) . . . . ? C16 C11 C12 C13 -1.5(4) . . . . ? C10 C11 C12 C13 179.0(3) . . . . ? C11 C12 C13 C14 1.0(4) . . . . ? C12 C13 C14 C15 0.0(4) . . . . ? C12 C13 C14 N2 -179.8(2) . . . . ? C13 C14 C15 C16 -0.6(4) . . . . ? N2 C14 C15 C16 179.3(2) . . . . ? C12 C11 C16 C15 0.9(4) . . . . ? C10 C11 C16 C15 -179.5(3) . . . . ? C14 C15 C16 C11 0.1(4) . . . . ? C17 C18 C19 C20 172.2(3) . . . . ? C17 C18 C19 C24 -7.6(4) . . . . ? C24 C19 C20 C21 0.5(4) . . . . ? C18 C19 C20 C21 -179.3(3) . . . . ? C19 C20 C21 C22 -0.6(4) . . . . ? C20 C21 C22 C23 -0.3(4) . . . . ? C20 C21 C22 N4 179.7(2) . . . . ? C21 C22 C23 C24 1.3(4) . . . . ? N4 C22 C23 C24 -178.7(3) . . . . ? C20 C19 C24 C23 0.5(4) . . . . ? C18 C19 C24 C23 -179.7(3) . . . . ? C22 C23 C24 C19 -1.4(4) . . . . ? C25 C26 C27 C28 -179.2(3) . . . . ? C25 C26 C27 C32 1.4(4) . . . . ? C32 C27 C28 C29 -1.8(4) . . . . ? C26 C27 C28 C29 178.8(3) . . . . ? C27 C28 C29 C30 0.4(4) . . . . ? C28 C29 C30 C31 1.8(4) . . . . ? C28 C29 C30 N3 -179.7(2) . . . . ? C29 C30 C31 C32 -2.6(4) . . . . ? N3 C30 C31 C32 178.9(2) . . . . ? C30 C31 C32 C27 1.2(4) . . . . ? C28 C27 C32 C31 1.0(4) . . . . ? C26 C27 C32 C31 -179.6(3) . . . . ? O2 C33 C34 O3 0.1(3) . . . . ? O1 C33 C34 O3 178.6(2) . . . . ? O2 C33 C34 C35 -120.5(2) . . . . ? O1 C33 C34 C35 58.0(3) . . . . ? O3 C34 C35 O4 -75.0(3) . . . . ? C33 C34 C35 O4 45.1(3) . . . . ? O3 C34 C35 C36 46.2(3) . . . . ? C33 C34 C35 C36 166.3(2) . . . . ? O4 C35 C36 O6 -1.4(3) . . . . ? C34 C35 C36 O6 -122.7(3) . . . . ? O4 C35 C36 O5 177.6(2) . . . . ? C34 C35 C36 O5 56.2(3) . . . . ? O8 C37 C38 O9 -0.3(3) . . . . ? O7 C37 C38 O9 179.3(2) . . . . ? O8 C37 C38 C39 -120.6(2) . . . . ? O7 C37 C38 C39 59.0(3) . . . . ? O9 C38 C39 O10 -73.7(3) . . . . ? C37 C38 C39 O10 46.3(3) . . . . ? O9 C38 C39 C40 47.5(3) . . . . ? C37 C38 C39 C40 167.4(2) . . . . ? O10 C39 C40 O12 -7.4(3) . . . . ? C38 C39 C40 O12 -128.1(3) . . . . ? O10 C39 C40 O11 173.4(2) . . . . ? C38 C39 C40 O11 52.7(3) . . . . ? O13 C41 C42 O15 -2.3(3) . . . . ? O14 C41 C42 O15 178.8(2) . . . . ? O13 C41 C42 C43 -123.4(2) . . . . ? O14 C41 C42 C43 57.8(3) . . . . ? O15 C42 C43 O16 -68.1(3) . . . . ? C41 C42 C43 O16 53.3(3) . . . . ? O15 C42 C43 C44 56.8(3) . . . . ? C41 C42 C43 C44 178.2(2) . . . . ? O16 C43 C44 O18 -162.8(2) . . . . ? C42 C43 C44 O18 73.5(3) . . . . ? O16 C43 C44 O17 21.0(3) . . . . ? C42 C43 C44 O17 -102.8(3) . . . . ? O19 C45 C46 O21 -3.4(3) . . . . ? O20 C45 C46 O21 177.7(2) . . . . ? O19 C45 C46 C47 -124.2(2) . . . . ? O20 C45 C46 C47 56.9(3) . . . . ? O21 C46 C47 O22 -68.9(3) . . . . ? C45 C46 C47 O22 52.6(3) . . . . ? O21 C46 C47 C48 55.9(3) . . . . ? C45 C46 C47 C48 177.4(2) . . . . ? O22 C47 C48 O24 -165.6(2) . . . . ? C46 C47 C48 O24 71.6(3) . . . . ? O22 C47 C48 O23 17.7(3) . . . . ? C46 C47 C48 O23 -105.0(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1D O9 0.89 2.00 2.879(3) 169.5 1_545 N1 H1E O1 0.89 2.37 3.217(3) 159.6 . N1 H1F O8 0.89 1.86 2.730(3) 166.4 1_445 N2 H2C O14 0.89 1.90 2.784(3) 171.5 . N2 H2D O21 0.89 1.94 2.781(3) 157.2 1_545 N2 H2E O19 0.89 1.81 2.677(3) 163.5 1_445 N3 H3A O13 0.89 1.83 2.708(3) 167.0 . N3 H3B O20 0.89 1.90 2.778(3) 169.5 . N3 H3C O15 0.89 1.92 2.746(3) 153.7 1_655 N4 H4A O3 0.89 1.97 2.860(3) 174.4 . N4 H4B O7 0.89 2.40 3.250(3) 159.5 1_455 N4 H4B O10 0.89 2.48 2.936(3) 112.4 1_455 N4 H4C O2 0.89 1.90 2.767(3) 165.6 1_455 O3 H3 O2 0.82 2.07 2.579(3) 120.2 . O3 H3 O12 0.82 2.65 3.051(3) 111.7 . O4 H4D O6 0.82 2.13 2.627(3) 118.8 . O5 H5A O1 0.82 1.78 2.587(3) 165.7 1_455 O9 H9 O8 0.82 2.08 2.578(3) 119.3 . O10 H10 O12 0.82 2.15 2.637(3) 117.8 . O11 H11 O7 0.82 1.79 2.596(3) 169.6 1_455 O15 H15A O13 0.82 2.09 2.589(2) 119.4 . O15 H15A O24 0.82 2.09 2.726(3) 134.3 . O16 H16A O7 0.82 2.05 2.723(3) 139.8 1_456 O17 H17 O14 0.82 1.73 2.548(3) 172.7 1_455 O21 H21A O18 0.82 2.08 2.710(3) 133.2 1_665 O21 H21A O19 0.82 2.09 2.590(2) 119.4 . O22 H22 O1 0.82 2.07 2.740(3) 138.8 1_566 O23 H23A O20 0.82 1.72 2.540(3) 175.2 1_455 _diffrn_measured_fraction_theta_max 0.974 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.974 _refine_diff_density_max 0.228 _refine_diff_density_min -0.254 _refine_diff_density_rms 0.045 #============================================END data_wudh_LTP(123K) _database_code_depnum_ccdc_archive 'CCDC 773838' #TrackingRef '- 1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C8 H12 N, C4 H5 O6' _chemical_formula_sum 'C12 H17 N O6' _chemical_formula_weight 271.27 _chemical_absolute_configuration syn 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 triclinic _symmetry_space_group_name_H-M 'P 1' _symmetry_space_group_name_Hall 'P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' _cell_length_a 7.4606(12) _cell_length_b 11.9298(18) _cell_length_c 14.8726(9) _cell_angle_alpha 95.338(2) _cell_angle_beta 91.9500(10) _cell_angle_gamma 107.9160(10) _cell_volume 1251.3(3) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 3664 _cell_measurement_theta_min 3.1892 _cell_measurement_theta_max 27.5087 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.440 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 576 _exptl_absorpt_coefficient_mu 0.116 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.962 _exptl_absorpt_correction_T_max 0.970 _exptl_absorpt_process_details 'CrystalClear (Rigaku, 2005)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(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 'Mercury2 (2x2 bin mode)' _diffrn_measurement_method CCD_Profile_fitting _diffrn_detector_area_resol_mean 13.6612 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13753 _diffrn_reflns_av_R_equivalents 0.0298 _diffrn_reflns_av_sigmaI/netI 0.0375 _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 -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.11 _diffrn_reflns_theta_max 27.49 _reflns_number_total 5681 _reflns_number_gt 4661 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku, 2005)' _computing_cell_refinement CrystalClear _computing_data_reduction CrystalClear _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material SHELXTL _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^)+(0.0508P)^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 ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 10(10) _refine_ls_number_reflns 5681 _refine_ls_number_parameters 705 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0495 _refine_ls_R_factor_gt 0.0386 _refine_ls_wR_factor_ref 0.0929 _refine_ls_wR_factor_gt 0.0867 _refine_ls_goodness_of_fit_ref 1.001 _refine_ls_restrained_S_all 1.001 _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 C1 C 0.6261(5) 0.2244(3) 0.2634(2) 0.0367(8) Uani 1 1 d . . . H1A H 0.6826 0.1708 0.2881 0.055 Uiso 1 1 calc R . . H1B H 0.6321 0.2179 0.1988 0.055 Uiso 1 1 calc R . . H1C H 0.4965 0.2048 0.2781 0.055 Uiso 1 1 calc R . . C2 C 0.7309(4) 0.3492(3) 0.3026(2) 0.0277(7) Uani 1 1 d . . . H2A H 0.6671 0.4014 0.2797 0.033 Uiso 1 1 calc R . . H2B H 0.8564 0.3709 0.2803 0.033 Uiso 1 1 calc R . . C3 C 0.7510(4) 0.3724(3) 0.4057(2) 0.0211(6) Uani 1 1 d . . . C4 C 0.6812(4) 0.2836(3) 0.4610(2) 0.0232(7) Uani 1 1 d . . . H4 H 0.6197 0.2067 0.4348 0.028 Uiso 1 1 calc R . . C5 C 0.7013(4) 0.3072(3) 0.5550(2) 0.0195(6) Uani 1 1 d . . . H5 H 0.6557 0.2466 0.5913 0.023 Uiso 1 1 calc R . . C6 C 0.7897(4) 0.4217(2) 0.59314(18) 0.0141(5) Uani 1 1 d . . . C7 C 0.8642(4) 0.5125(3) 0.5402(2) 0.0213(6) Uani 1 1 d . . . H7 H 0.9255 0.5892 0.5667 0.026 Uiso 1 1 calc R . . C8 C 0.8451(4) 0.4862(3) 0.4466(2) 0.0223(6) Uani 1 1 d . . . H8 H 0.8964 0.5462 0.4105 0.027 Uiso 1 1 calc R . . C9 C 0.3420(4) 0.4726(3) 0.5094(2) 0.0272(7) Uani 1 1 d . . . H9A H 0.4639 0.4949 0.4849 0.041 Uiso 1 1 calc R . . H9B H 0.3571 0.4715 0.5736 0.041 Uiso 1 1 calc R . . H9C H 0.2785 0.5288 0.4970 0.041 Uiso 1 1 calc R . . C10 C 0.2258(4) 0.3499(3) 0.46607(19) 0.0224(7) Uani 1 1 d . . . H10A H 0.2833 0.2928 0.4856 0.027 Uiso 1 1 calc R . . H10B H 0.1006 0.3309 0.4886 0.027 Uiso 1 1 calc R . . C11 C 0.2056(4) 0.3352(3) 0.36363(19) 0.0179(6) Uani 1 1 d . . . C12 C 0.1207(4) 0.2230(3) 0.3180(2) 0.0202(6) Uani 1 1 d . . . H12 H 0.0762 0.1590 0.3513 0.024 Uiso 1 1 calc R . . C13 C 0.1004(4) 0.2037(2) 0.2244(2) 0.0190(6) Uani 1 1 d . . . H13 H 0.0440 0.1277 0.1953 0.023 Uiso 1 1 calc R . . C14 C 0.1653(4) 0.2989(2) 0.17460(19) 0.0158(6) Uani 1 1 d . . . C15 C 0.2480(4) 0.4115(2) 0.21754(18) 0.0168(6) Uani 1 1 d . . . H15 H 0.2892 0.4753 0.1838 0.020 Uiso 1 1 calc R . . C16 C 0.2698(4) 0.4294(2) 0.31179(18) 0.0180(6) Uani 1 1 d . . . H16 H 0.3281 0.5054 0.3405 0.022 Uiso 1 1 calc R . . C17 C 0.7837(5) 0.9684(3) 0.5095(2) 0.0297(8) Uani 1 1 d . . . H17A H 0.8889 1.0236 0.4855 0.044 Uiso 1 1 calc R . . H17B H 0.8074 0.9707 0.5736 0.044 Uiso 1 1 calc R . . H17C H 0.6715 0.9894 0.4978 0.044 Uiso 1 1 calc R . . C18 C 0.7575(4) 0.8441(3) 0.4646(2) 0.0254(7) Uani 1 1 d . . . H18A H 0.8673 0.8215 0.4815 0.031 Uiso 1 1 calc R . . H18B H 0.6489 0.7898 0.4884 0.031 Uiso 1 1 calc R . . C19 C 0.7295(4) 0.8287(3) 0.36210(19) 0.0189(6) Uani 1 1 d . . . C20 C 0.7019(4) 0.7176(3) 0.3148(2) 0.0212(6) Uani 1 1 d . . . H20 H 0.6984 0.6537 0.3468 0.025 Uiso 1 1 calc R . . C21 C 0.6793(4) 0.7000(3) 0.2205(2) 0.0187(6) Uani 1 1 d . . . H21 H 0.6615 0.6255 0.1897 0.022 Uiso 1 1 calc R . . C22 C 0.6840(4) 0.7957(2) 0.17348(17) 0.0130(5) Uani 1 1 d . . . C23 C 0.7102(4) 0.9066(2) 0.21828(18) 0.0171(6) Uani 1 1 d . . . H23 H 0.7127 0.9702 0.1860 0.021 Uiso 1 1 calc R . . C24 C 0.7327(4) 0.9223(3) 0.31242(19) 0.0196(6) Uani 1 1 d . . . H24 H 0.7502 0.9970 0.3427 0.023 Uiso 1 1 calc R . . C25 C 0.2025(5) 0.7311(3) 0.2598(2) 0.0339(8) Uani 1 1 d . . . H25A H 0.3066 0.7084 0.2828 0.051 Uiso 1 1 calc R . . H25B H 0.2035 0.7288 0.1952 0.051 Uiso 1 1 calc R . . H25C H 0.0862 0.6772 0.2757 0.051 Uiso 1 1 calc R . . C26 C 0.2203(4) 0.8551(3) 0.30040(19) 0.0271(7) Uani 1 1 d . . . H26A H 0.3277 0.9097 0.2760 0.032 Uiso 1 1 calc R . . H26B H 0.1086 0.8738 0.2806 0.032 Uiso 1 1 calc R . . C27 C 0.2439(4) 0.8774(3) 0.40227(19) 0.0200(6) Uani 1 1 d . . . C28 C 0.2404(4) 0.7877(3) 0.4566(2) 0.0200(6) Uani 1 1 d . . . H28 H 0.2240 0.7115 0.4295 0.024 Uiso 1 1 calc R . . C29 C 0.2610(4) 0.8097(2) 0.5506(2) 0.0180(6) Uani 1 1 d . . . H29 H 0.2582 0.7488 0.5859 0.022 Uiso 1 1 calc R . . C30 C 0.2856(4) 0.9230(3) 0.59057(19) 0.0172(6) Uani 1 1 d . . . C31 C 0.2912(4) 1.0137(3) 0.5387(2) 0.0203(6) Uani 1 1 d . . . H31 H 0.3079 1.0898 0.5661 0.024 Uiso 1 1 calc R . . C32 C 0.2715(4) 0.9902(3) 0.4450(2) 0.0229(6) Uani 1 1 d . . . H32 H 0.2770 1.0518 0.4101 0.028 Uiso 1 1 calc R . . C33 C 0.6590(3) 0.0750(2) -0.01222(18) 0.0145(5) Uani 1 1 d . . . C34 C 0.4511(3) 0.0705(2) -0.02666(18) 0.0140(5) Uani 1 1 d . . . H34 H 0.4215 0.0729 -0.0910 0.017 Uiso 1 1 calc R . . C35 C 0.3210(3) -0.0429(2) 0.00407(18) 0.0148(5) Uani 1 1 d . . . H35 H 0.3162 -0.1097 -0.0406 0.018 Uiso 1 1 calc R . . C36 C 0.1229(4) -0.0356(2) 0.01292(19) 0.0151(5) Uani 1 1 d . . . C37 C 1.1768(4) 0.5752(2) -0.01433(18) 0.0151(5) Uani 1 1 d . . . C38 C 0.9693(3) 0.5728(2) -0.02726(17) 0.0129(5) Uani 1 1 d . . . H38 H 0.9382 0.5761 -0.0913 0.016 Uiso 1 1 calc R . . C39 C 0.8400(3) 0.4573(2) 0.00343(17) 0.0146(5) Uani 1 1 d . . . H39 H 0.8378 0.3912 -0.0414 0.018 Uiso 1 1 calc R . . C40 C 0.6392(3) 0.4614(2) 0.01135(18) 0.0130(5) Uani 1 1 d . . . C41 C 0.3471(4) 0.2688(2) 0.74033(17) 0.0143(5) Uani 1 1 d . . . C42 C 0.1331(3) 0.2395(2) 0.72236(18) 0.0138(5) Uani 1 1 d . . . H42 H 0.0917 0.1828 0.6679 0.017 Uiso 1 1 calc R . . C43 C 0.0297(3) 0.1841(2) 0.80288(17) 0.0125(5) Uani 1 1 d . . . H43 H 0.0506 0.1075 0.8068 0.015 Uiso 1 1 calc R . . C44 C -0.1814(3) 0.1611(2) 0.77902(17) 0.0129(5) Uani 1 1 d . . . C45 C 0.8511(3) 0.7692(2) 0.74013(17) 0.0130(5) Uani 1 1 d . . . C46 C 0.6377(3) 0.7387(2) 0.72176(17) 0.0128(5) Uani 1 1 d . . . H46 H 0.5976 0.6820 0.6673 0.015 Uiso 1 1 calc R . . C47 C 0.5327(3) 0.6827(2) 0.80221(17) 0.0140(5) Uani 1 1 d . . . H47 H 0.5522 0.6057 0.8061 0.017 Uiso 1 1 calc R . . C48 C 0.3233(3) 0.6619(2) 0.77772(17) 0.0120(5) Uani 1 1 d . . . N1 N 0.8074(3) 0.4465(2) 0.69189(15) 0.0159(5) Uani 1 1 d . . . H1D H 0.6953 0.4161 0.7139 0.024 Uiso 1 1 calc R . . H1E H 0.8486 0.5245 0.7072 0.024 Uiso 1 1 calc R . . H1F H 0.8891 0.4140 0.7146 0.024 Uiso 1 1 calc R . . N2 N 0.1452(3) 0.2791(2) 0.07547(14) 0.0140(5) Uani 1 1 d . . . H2C H 0.2295 0.2454 0.0555 0.021 Uiso 1 1 calc R . . H2D H 0.1645 0.3482 0.0531 0.021 Uiso 1 1 calc R . . H2E H 0.0294 0.2318 0.0577 0.021 Uiso 1 1 calc R . . N3 N 0.6577(3) 0.7782(2) 0.07437(15) 0.0150(5) Uani 1 1 d . . . H3A H 0.7433 0.7473 0.0519 0.023 Uiso 1 1 calc R . . H3B H 0.6713 0.8476 0.0534 0.023 Uiso 1 1 calc R . . H3C H 0.5424 0.7291 0.0577 0.023 Uiso 1 1 calc R . . N4 N 0.3056(3) 0.94548(19) 0.68955(14) 0.0127(4) Uani 1 1 d . . . H4A H 0.1945 0.9134 0.7120 0.019 Uiso 1 1 calc R . . H4B H 0.3451 1.0233 0.7059 0.019 Uiso 1 1 calc R . . H4C H 0.3892 0.9134 0.7109 0.019 Uiso 1 1 calc R . . O1 O 0.7033(3) -0.01076(17) -0.05230(14) 0.0211(5) Uani 1 1 d . . . O2 O 0.7654(3) 0.16009(17) 0.03787(13) 0.0199(4) Uani 1 1 d . . . O3 O 0.4258(2) 0.17135(15) 0.02456(13) 0.0183(4) Uani 1 1 d . . . H3 H 0.5247 0.2093 0.0536 0.027 Uiso 1 1 calc R . . O4 O 0.3920(3) -0.06247(18) 0.08891(13) 0.0217(4) Uani 1 1 d . . . H4D H 0.3131 -0.0646 0.1263 0.033 Uiso 1 1 calc R . . O5 O 0.0469(3) -0.04971(17) 0.08369(13) 0.0243(5) Uani 1 1 d . . . O6 O 0.0477(2) -0.01338(18) -0.06121(12) 0.0211(4) Uani 1 1 d . . . H6 H -0.0556 -0.0056 -0.0515 0.032 Uiso 1 1 calc R . . O7 O 1.2210(3) 0.49098(17) -0.05576(14) 0.0234(5) Uani 1 1 d . . . O8 O 1.2818(3) 0.65864(16) 0.03757(13) 0.0186(4) Uani 1 1 d . . . O9 O 0.9442(2) 0.67194(16) 0.02531(13) 0.0179(4) Uani 1 1 d . . . H9 H 1.0438 0.7101 0.0537 0.027 Uiso 1 1 calc R . . O10 O 0.9134(3) 0.43882(17) 0.08738(13) 0.0207(4) Uani 1 1 d . . . H10 H 0.8294 0.4246 0.1228 0.031 Uiso 1 1 calc R . . O11 O 0.5671(2) 0.49049(18) -0.06079(12) 0.0212(4) Uani 1 1 d . . . H11 H 0.4571 0.4869 -0.0536 0.032 Uiso 1 1 calc R . . O12 O 0.5597(3) 0.43898(17) 0.08039(12) 0.0225(4) Uani 1 1 d . . . O13 O 0.4081(2) 0.18406(16) 0.75576(13) 0.0187(4) Uani 1 1 d . . . O14 O 0.4435(2) 0.37307(15) 0.73694(13) 0.0179(4) Uani 1 1 d . . . O15 O 0.0882(2) 0.34318(16) 0.70845(13) 0.0177(4) Uani 1 1 d . . . H15A H 0.1844 0.4004 0.7161 0.027 Uiso 1 1 calc R . . O16 O 0.0976(2) 0.25485(15) 0.88515(11) 0.0162(4) Uani 1 1 d . . . H16A H 0.1041 0.3236 0.8793 0.024 Uiso 1 1 calc R . . O17 O -0.2687(3) 0.08168(17) 0.72272(13) 0.0198(4) Uani 1 1 d . . . O18 O -0.2517(2) 0.23852(16) 0.82090(13) 0.0160(4) Uani 1 1 d . . . H18 H -0.3644 0.2211 0.8057 0.024 Uiso 1 1 calc R . . O19 O 0.9128(2) 0.68509(16) 0.75635(13) 0.0192(4) Uani 1 1 d . . . O20 O 0.9471(2) 0.87324(16) 0.73548(13) 0.0183(4) Uani 1 1 d . . . O21 O 0.5901(2) 0.84175(16) 0.70776(13) 0.0187(4) Uani 1 1 d . . . H21A H 0.6865 0.8987 0.7112 0.028 Uiso 1 1 calc R . . O22 O 0.6011(2) 0.75384(15) 0.88415(12) 0.0167(4) Uani 1 1 d . . . H22 H 0.5979 0.8212 0.8796 0.025 Uiso 1 1 calc R . . O23 O 0.2370(2) 0.58372(16) 0.71908(13) 0.0175(4) Uani 1 1 d . . . O24 O 0.2513(3) 0.73689(16) 0.82086(13) 0.0176(4) Uani 1 1 d . . . H24A H 0.1381 0.7184 0.8062 0.026 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 C1 0.0333(18) 0.059(2) 0.0173(17) -0.0017(16) -0.0015(13) 0.0159(17) C2 0.0235(15) 0.047(2) 0.0192(16) 0.0079(14) 0.0041(12) 0.0189(15) C3 0.0148(13) 0.0335(17) 0.0189(15) 0.0040(13) 0.0015(10) 0.0129(12) C4 0.0195(14) 0.0232(16) 0.0258(17) 0.0031(13) 0.0009(12) 0.0051(12) C5 0.0166(14) 0.0200(15) 0.0199(15) 0.0039(11) 0.0020(11) 0.0021(11) C6 0.0132(12) 0.0183(14) 0.0127(13) 0.0054(11) -0.0007(10) 0.0068(11) C7 0.0164(13) 0.0194(15) 0.0281(16) 0.0064(12) -0.0007(11) 0.0047(12) C8 0.0198(14) 0.0267(16) 0.0239(16) 0.0130(13) 0.0044(11) 0.0091(12) C9 0.0266(16) 0.0413(19) 0.0145(15) -0.0023(13) 0.0012(12) 0.0130(15) C10 0.0210(15) 0.0354(18) 0.0137(14) 0.0030(12) 0.0015(11) 0.0130(13) C11 0.0150(13) 0.0262(16) 0.0144(14) 0.0030(11) 0.0006(10) 0.0090(12) C12 0.0198(14) 0.0233(15) 0.0201(15) 0.0067(12) 0.0032(11) 0.0088(12) C13 0.0201(14) 0.0137(14) 0.0231(15) -0.0001(12) 0.0001(11) 0.0058(11) C14 0.0107(12) 0.0181(14) 0.0187(14) -0.0016(11) -0.0003(10) 0.0058(10) C15 0.0187(14) 0.0159(14) 0.0155(14) 0.0012(11) 0.0036(10) 0.0046(11) C16 0.0164(13) 0.0202(15) 0.0149(14) -0.0028(11) 0.0001(10) 0.0034(11) C17 0.0211(15) 0.050(2) 0.0168(15) -0.0025(14) 0.0016(11) 0.0116(15) C18 0.0195(14) 0.0413(19) 0.0162(15) 0.0064(13) 0.0037(11) 0.0092(14) C19 0.0142(13) 0.0271(16) 0.0164(14) 0.0031(12) 0.0020(10) 0.0074(12) C20 0.0210(14) 0.0224(15) 0.0224(15) 0.0085(12) 0.0013(11) 0.0083(12) C21 0.0182(14) 0.0163(14) 0.0213(15) 0.0000(11) 0.0004(11) 0.0055(11) C22 0.0126(12) 0.0175(14) 0.0082(12) 0.0011(10) -0.0011(9) 0.0040(10) C23 0.0169(13) 0.0175(14) 0.0175(14) 0.0021(11) 0.0010(10) 0.0061(11) C24 0.0193(14) 0.0199(15) 0.0194(15) -0.0030(12) 0.0010(11) 0.0074(12) C25 0.0313(17) 0.056(2) 0.0160(16) -0.0056(15) -0.0012(13) 0.0191(16) C26 0.0199(15) 0.047(2) 0.0161(15) 0.0068(14) 0.0016(11) 0.0124(14) C27 0.0119(13) 0.0323(17) 0.0163(14) 0.0059(12) 0.0007(10) 0.0068(12) C28 0.0204(14) 0.0236(15) 0.0153(14) -0.0004(12) -0.0019(11) 0.0071(12) C29 0.0175(14) 0.0157(14) 0.0210(15) 0.0038(11) 0.0007(11) 0.0051(11) C30 0.0085(12) 0.0221(15) 0.0205(15) 0.0015(12) 0.0014(10) 0.0042(11) C31 0.0164(13) 0.0212(15) 0.0241(16) 0.0057(12) 0.0018(11) 0.0062(12) C32 0.0201(15) 0.0277(16) 0.0235(16) 0.0118(13) 0.0028(11) 0.0083(13) C33 0.0087(12) 0.0155(13) 0.0188(14) 0.0047(11) 0.0039(10) 0.0018(10) C34 0.0094(12) 0.0165(13) 0.0166(13) 0.0014(10) 0.0003(9) 0.0049(10) C35 0.0137(12) 0.0156(13) 0.0158(13) 0.0015(10) -0.0003(9) 0.0059(10) C36 0.0133(12) 0.0102(12) 0.0194(14) -0.0016(10) 0.0026(10) 0.0008(10) C37 0.0129(12) 0.0187(14) 0.0145(13) 0.0029(11) 0.0004(10) 0.0058(11) C38 0.0135(12) 0.0132(13) 0.0121(12) -0.0002(10) -0.0010(9) 0.0049(10) C39 0.0137(12) 0.0157(13) 0.0149(13) -0.0014(10) -0.0021(9) 0.0062(10) C40 0.0118(12) 0.0095(12) 0.0164(13) -0.0004(10) 0.0011(9) 0.0018(10) C41 0.0125(12) 0.0195(14) 0.0125(13) 0.0007(10) 0.0024(9) 0.0073(11) C42 0.0102(11) 0.0154(13) 0.0161(13) 0.0000(10) -0.0003(9) 0.0052(10) C43 0.0088(11) 0.0133(13) 0.0152(13) 0.0018(10) -0.0002(9) 0.0032(10) C44 0.0096(11) 0.0142(13) 0.0150(13) 0.0029(10) 0.0036(9) 0.0032(10) C45 0.0111(12) 0.0147(13) 0.0128(13) -0.0015(10) 0.0012(9) 0.0043(10) C46 0.0091(11) 0.0132(13) 0.0168(13) 0.0031(10) 0.0010(9) 0.0042(9) C47 0.0114(12) 0.0163(13) 0.0158(13) 0.0014(10) 0.0004(9) 0.0065(10) C48 0.0130(12) 0.0102(12) 0.0152(13) 0.0058(10) 0.0021(9) 0.0057(10) N1 0.0123(11) 0.0155(12) 0.0203(12) 0.0026(10) 0.0019(9) 0.0047(9) N2 0.0132(10) 0.0182(12) 0.0110(11) -0.0031(9) -0.0012(8) 0.0071(9) N3 0.0124(10) 0.0178(12) 0.0145(12) -0.0008(9) -0.0003(8) 0.0050(9) N4 0.0109(10) 0.0120(11) 0.0143(11) 0.0018(9) 0.0009(8) 0.0025(9) O1 0.0115(9) 0.0201(11) 0.0314(12) -0.0066(9) -0.0026(8) 0.0075(8) O2 0.0124(9) 0.0211(10) 0.0228(11) -0.0041(8) -0.0013(8) 0.0025(8) O3 0.0151(9) 0.0136(9) 0.0259(11) -0.0046(8) -0.0009(7) 0.0064(7) O4 0.0219(10) 0.0258(11) 0.0197(10) 0.0096(9) -0.0001(8) 0.0087(9) O5 0.0178(10) 0.0304(12) 0.0227(11) 0.0035(9) 0.0068(8) 0.0035(9) O6 0.0116(9) 0.0325(11) 0.0214(10) 0.0073(9) 0.0031(7) 0.0087(8) O7 0.0137(10) 0.0227(11) 0.0338(12) -0.0054(9) 0.0000(8) 0.0081(8) O8 0.0147(9) 0.0202(10) 0.0177(10) -0.0041(8) 0.0001(7) 0.0028(8) O9 0.0139(9) 0.0148(9) 0.0257(11) -0.0013(8) -0.0004(7) 0.0066(7) O10 0.0194(10) 0.0240(11) 0.0201(10) 0.0067(9) -0.0006(7) 0.0077(9) O11 0.0121(9) 0.0340(12) 0.0219(10) 0.0092(9) 0.0025(7) 0.0116(9) O12 0.0178(10) 0.0306(12) 0.0181(10) 0.0042(9) 0.0055(7) 0.0049(8) O13 0.0115(8) 0.0155(9) 0.0304(11) 0.0003(8) 0.0010(7) 0.0070(7) O14 0.0114(8) 0.0167(10) 0.0258(10) 0.0040(8) 0.0039(7) 0.0041(7) O15 0.0104(8) 0.0162(10) 0.0282(11) 0.0110(8) 0.0016(7) 0.0041(7) O16 0.0169(9) 0.0173(9) 0.0135(9) 0.0016(7) -0.0019(7) 0.0044(8) O17 0.0129(9) 0.0196(10) 0.0251(11) -0.0040(8) -0.0032(7) 0.0048(8) O18 0.0097(8) 0.0174(10) 0.0201(10) -0.0035(8) -0.0021(7) 0.0048(8) O19 0.0117(8) 0.0150(9) 0.0310(11) 0.0003(8) -0.0018(7) 0.0056(7) O20 0.0109(8) 0.0187(10) 0.0246(10) 0.0028(8) 0.0023(7) 0.0034(7) O21 0.0111(9) 0.0157(10) 0.0305(11) 0.0076(8) 0.0005(8) 0.0045(7) O22 0.0162(9) 0.0174(10) 0.0153(9) -0.0007(7) -0.0029(7) 0.0049(8) O23 0.0124(9) 0.0159(10) 0.0216(10) -0.0050(8) -0.0018(7) 0.0031(7) O24 0.0118(9) 0.0210(11) 0.0212(10) -0.0010(8) 0.0019(7) 0.0078(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 C1 C2 1.504(5) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 C3 1.526(4) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.386(4) . ? C3 C8 1.392(4) . ? C4 C5 1.394(4) . ? C4 H4 0.9300 . ? C5 C6 1.379(4) . ? C5 H5 0.9300 . ? C6 C7 1.385(4) . ? C6 N1 1.464(3) . ? C7 C8 1.391(4) . ? C7 H7 0.9300 . ? C8 H8 0.9300 . ? C9 C10 1.522(4) . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 C11 1.514(4) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.390(4) . ? C11 C16 1.394(4) . ? C12 C13 1.386(4) . ? C12 H12 0.9300 . ? C13 C14 1.384(4) . ? C13 H13 0.9300 . ? C14 C15 1.377(4) . ? C14 N2 1.466(3) . ? C15 C16 1.395(4) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? C17 C18 1.521(4) . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 C19 1.517(4) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 C24 1.390(4) . ? C19 C20 1.394(4) . ? C20 C21 1.396(4) . ? C20 H20 0.9300 . ? C21 C22 1.384(4) . ? C21 H21 0.9300 . ? C22 C23 1.379(3) . ? C22 N3 1.467(3) . ? C23 C24 1.393(4) . ? C23 H23 0.9300 . ? C24 H24 0.9300 . ? C25 C26 1.510(5) . ? C25 H25A 0.9600 . ? C25 H25B 0.9600 . ? C25 H25C 0.9600 . ? C26 C27 1.508(4) . ? C26 H26A 0.9700 . ? C26 H26B 0.9700 . ? C27 C32 1.386(4) . ? C27 C28 1.394(4) . ? C28 C29 1.392(4) . ? C28 H28 0.9300 . ? C29 C30 1.380(4) . ? C29 H29 0.9300 . ? C30 C31 1.378(4) . ? C30 N4 1.466(3) . ? C31 C32 1.388(4) . ? C31 H31 0.9300 . ? C32 H32 0.9300 . ? C33 O2 1.241(3) . ? C33 O1 1.272(3) . ? C33 C34 1.542(3) . ? C34 O3 1.430(3) . ? C34 C35 1.522(3) . ? C34 H34 0.9800 . ? C35 O4 1.419(3) . ? C35 C36 1.517(3) . ? C35 H35 0.9800 . ? C36 O5 1.214(3) . ? C36 O6 1.305(3) . ? C37 O8 1.239(3) . ? C37 O7 1.265(3) . ? C37 C38 1.545(3) . ? C38 O9 1.421(3) . ? C38 C39 1.538(3) . ? C38 H38 0.9800 . ? C39 O10 1.410(3) . ? C39 C40 1.522(3) . ? C39 H39 0.9800 . ? C40 O12 1.214(3) . ? C40 O11 1.306(3) . ? C41 O14 1.238(3) . ? C41 O13 1.265(3) . ? C41 C42 1.534(3) . ? C42 O15 1.408(3) . ? C42 C43 1.537(3) . ? C42 H42 0.9800 . ? C43 O16 1.403(3) . ? C43 C44 1.536(3) . ? C43 H43 0.9800 . ? C44 O17 1.208(3) . ? C44 O18 1.315(3) . ? C45 O20 1.237(3) . ? C45 O19 1.265(3) . ? C45 C46 1.529(3) . ? C46 O21 1.411(3) . ? C46 C47 1.543(3) . ? C46 H46 0.9800 . ? C47 O22 1.401(3) . ? C47 C48 1.530(3) . ? C47 H47 0.9800 . ? C48 O23 1.219(3) . ? C48 O24 1.309(3) . ? N1 H1D 0.8900 . ? N1 H1E 0.8900 . ? N1 H1F 0.8900 . ? N2 H2C 0.8900 . ? N2 H2D 0.8900 . ? N2 H2E 0.8900 . ? N3 H3A 0.8900 . ? N3 H3B 0.8900 . ? N3 H3C 0.8900 . ? N4 H4A 0.8900 . ? N4 H4B 0.8900 . ? N4 H4C 0.8900 . ? O3 H3 0.8200 . ? O4 H4D 0.8200 . ? O6 H6 0.8200 . ? O9 H9 0.8200 . ? O10 H10 0.8200 . ? O11 H11 0.8200 . ? O15 H15A 0.8200 . ? O16 H16A 0.8200 . ? O18 H18 0.8200 . ? O21 H21A 0.8200 . ? O22 H22 0.8200 . ? O24 H24A 0.8200 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C1 C2 C3 116.3(3) . . ? C1 C2 H2A 108.2 . . ? C3 C2 H2A 108.2 . . ? C1 C2 H2B 108.2 . . ? C3 C2 H2B 108.2 . . ? H2A C2 H2B 107.4 . . ? C4 C3 C8 118.1(3) . . ? C4 C3 C2 122.5(3) . . ? C8 C3 C2 119.4(3) . . ? C3 C4 C5 121.3(3) . . ? C3 C4 H4 119.4 . . ? C5 C4 H4 119.4 . . ? C6 C5 C4 119.0(3) . . ? C6 C5 H5 120.5 . . ? C4 C5 H5 120.5 . . ? C5 C6 C7 121.4(3) . . ? C5 C6 N1 118.8(2) . . ? C7 C6 N1 119.8(2) . . ? C6 C7 C8 118.4(3) . . ? C6 C7 H7 120.8 . . ? C8 C7 H7 120.8 . . ? C7 C8 C3 121.7(3) . . ? C7 C8 H8 119.2 . . ? C3 C8 H8 119.2 . . ? C10 C9 H9A 109.5 . . ? C10 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C10 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C11 C10 C9 115.4(3) . . ? C11 C10 H10A 108.4 . . ? C9 C10 H10A 108.4 . . ? C11 C10 H10B 108.4 . . ? C9 C10 H10B 108.4 . . ? H10A C10 H10B 107.5 . . ? C12 C11 C16 117.6(3) . . ? C12 C11 C10 119.3(3) . . ? C16 C11 C10 123.0(2) . . ? C13 C12 C11 122.0(3) . . ? C13 C12 H12 119.0 . . ? C11 C12 H12 119.0 . . ? C14 C13 C12 119.1(3) . . ? C14 C13 H13 120.4 . . ? C12 C13 H13 120.4 . . ? C15 C14 C13 120.5(3) . . ? C15 C14 N2 120.1(2) . . ? C13 C14 N2 119.5(2) . . ? C14 C15 C16 119.8(3) . . ? C14 C15 H15 120.1 . . ? C16 C15 H15 120.1 . . ? C11 C16 C15 120.9(3) . . ? C11 C16 H16 119.5 . . ? C15 C16 H16 119.5 . . ? C18 C17 H17A 109.5 . . ? C18 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C18 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C19 C18 C17 115.4(3) . . ? C19 C18 H18A 108.4 . . ? C17 C18 H18A 108.4 . . ? C19 C18 H18B 108.4 . . ? C17 C18 H18B 108.4 . . ? H18A C18 H18B 107.5 . . ? C24 C19 C20 117.9(3) . . ? C24 C19 C18 122.4(3) . . ? C20 C19 C18 119.7(3) . . ? C19 C20 C21 121.5(3) . . ? C19 C20 H20 119.2 . . ? C21 C20 H20 119.2 . . ? C22 C21 C20 118.8(3) . . ? C22 C21 H21 120.6 . . ? C20 C21 H21 120.6 . . ? C23 C22 C21 121.2(2) . . ? C23 C22 N3 119.5(2) . . ? C21 C22 N3 119.4(2) . . ? C22 C23 C24 119.2(3) . . ? C22 C23 H23 120.4 . . ? C24 C23 H23 120.4 . . ? C19 C24 C23 121.4(3) . . ? C19 C24 H24 119.3 . . ? C23 C24 H24 119.3 . . ? C26 C25 H25A 109.5 . . ? C26 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C26 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C27 C26 C25 116.2(3) . . ? C27 C26 H26A 108.2 . . ? C25 C26 H26A 108.2 . . ? C27 C26 H26B 108.2 . . ? C25 C26 H26B 108.2 . . ? H26A C26 H26B 107.4 . . ? C32 C27 C28 117.6(3) . . ? C32 C27 C26 120.1(3) . . ? C28 C27 C26 122.3(3) . . ? C29 C28 C27 121.5(3) . . ? C29 C28 H28 119.2 . . ? C27 C28 H28 119.2 . . ? C30 C29 C28 119.0(3) . . ? C30 C29 H29 120.5 . . ? C28 C29 H29 120.5 . . ? C31 C30 C29 120.8(3) . . ? C31 C30 N4 120.3(3) . . ? C29 C30 N4 118.9(3) . . ? C30 C31 C32 119.3(3) . . ? C30 C31 H31 120.4 . . ? C32 C31 H31 120.4 . . ? C27 C32 C31 121.7(3) . . ? C27 C32 H32 119.2 . . ? C31 C32 H32 119.2 . . ? O2 C33 O1 126.5(2) . . ? O2 C33 C34 117.3(2) . . ? O1 C33 C34 116.2(2) . . ? O3 C34 C35 109.9(2) . . ? O3 C34 C33 108.6(2) . . ? C35 C34 C33 110.2(2) . . ? O3 C34 H34 109.4 . . ? C35 C34 H34 109.4 . . ? C33 C34 H34 109.4 . . ? O4 C35 C36 109.1(2) . . ? O4 C35 C34 109.8(2) . . ? C36 C35 C34 111.0(2) . . ? O4 C35 H35 109.0 . . ? C36 C35 H35 109.0 . . ? C34 C35 H35 109.0 . . ? O5 C36 O6 125.3(2) . . ? O5 C36 C35 121.1(2) . . ? O6 C36 C35 113.7(2) . . ? O8 C37 O7 126.8(2) . . ? O8 C37 C38 116.1(2) . . ? O7 C37 C38 117.0(2) . . ? O9 C38 C39 109.8(2) . . ? O9 C38 C37 109.4(2) . . ? C39 C38 C37 109.1(2) . . ? O9 C38 H38 109.5 . . ? C39 C38 H38 109.5 . . ? C37 C38 H38 109.5 . . ? O10 C39 C40 110.1(2) . . ? O10 C39 C38 109.2(2) . . ? C40 C39 C38 111.3(2) . . ? O10 C39 H39 108.7 . . ? C40 C39 H39 108.7 . . ? C38 C39 H39 108.7 . . ? O12 C40 O11 125.5(2) . . ? O12 C40 C39 120.4(2) . . ? O11 C40 C39 114.1(2) . . ? O14 C41 O13 126.4(2) . . ? O14 C41 C42 116.5(2) . . ? O13 C41 C42 117.1(2) . . ? O15 C42 C41 110.0(2) . . ? O15 C42 C43 109.5(2) . . ? C41 C42 C43 110.2(2) . . ? O15 C42 H42 109.0 . . ? C41 C42 H42 109.0 . . ? C43 C42 H42 109.0 . . ? O16 C43 C44 114.1(2) . . ? O16 C43 C42 112.1(2) . . ? C44 C43 C42 106.0(2) . . ? O16 C43 H43 108.1 . . ? C44 C43 H43 108.1 . . ? C42 C43 H43 108.1 . . ? O17 C44 O18 124.4(2) . . ? O17 C44 C43 121.3(2) . . ? O18 C44 C43 114.2(2) . . ? O20 C45 O19 126.3(2) . . ? O20 C45 C46 116.8(2) . . ? O19 C45 C46 116.9(2) . . ? O21 C46 C45 110.2(2) . . ? O21 C46 C47 109.0(2) . . ? C45 C46 C47 110.6(2) . . ? O21 C46 H46 109.0 . . ? C45 C46 H46 109.0 . . ? C47 C46 H46 109.0 . . ? O22 C47 C48 114.1(2) . . ? O22 C47 C46 111.6(2) . . ? C48 C47 C46 105.5(2) . . ? O22 C47 H47 108.5 . . ? C48 C47 H47 108.5 . . ? C46 C47 H47 108.5 . . ? O23 C48 O24 124.3(2) . . ? O23 C48 C47 120.6(2) . . ? O24 C48 C47 115.0(2) . . ? C6 N1 H1D 109.5 . . ? C6 N1 H1E 109.5 . . ? H1D N1 H1E 109.5 . . ? C6 N1 H1F 109.5 . . ? H1D N1 H1F 109.5 . . ? H1E N1 H1F 109.5 . . ? C14 N2 H2C 109.5 . . ? C14 N2 H2D 109.5 . . ? H2C N2 H2D 109.5 . . ? C14 N2 H2E 109.5 . . ? H2C N2 H2E 109.5 . . ? H2D N2 H2E 109.5 . . ? C22 N3 H3A 109.5 . . ? C22 N3 H3B 109.5 . . ? H3A N3 H3B 109.5 . . ? C22 N3 H3C 109.5 . . ? H3A N3 H3C 109.5 . . ? H3B N3 H3C 109.5 . . ? C30 N4 H4A 109.5 . . ? C30 N4 H4B 109.5 . . ? H4A N4 H4B 109.5 . . ? C30 N4 H4C 109.5 . . ? H4A N4 H4C 109.5 . . ? H4B N4 H4C 109.5 . . ? C34 O3 H3 109.5 . . ? C35 O4 H4D 109.5 . . ? C36 O6 H6 109.5 . . ? C38 O9 H9 109.5 . . ? C39 O10 H10 109.5 . . ? C40 O11 H11 109.5 . . ? C42 O15 H15A 109.5 . . ? C43 O16 H16A 109.5 . . ? C44 O18 H18 109.5 . . ? C46 O21 H21A 109.5 . . ? C47 O22 H22 109.5 . . ? C48 O24 H24A 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 C1 C2 C3 C4 1.5(4) . . . . ? C1 C2 C3 C8 -179.4(3) . . . . ? C8 C3 C4 C5 1.0(4) . . . . ? C2 C3 C4 C5 -179.9(2) . . . . ? C3 C4 C5 C6 1.1(4) . . . . ? C4 C5 C6 C7 -2.2(4) . . . . ? C4 C5 C6 N1 178.9(2) . . . . ? C5 C6 C7 C8 1.1(4) . . . . ? N1 C6 C7 C8 -180.0(2) . . . . ? C6 C7 C8 C3 1.1(4) . . . . ? C4 C3 C8 C7 -2.1(4) . . . . ? C2 C3 C8 C7 178.8(2) . . . . ? C9 C10 C11 C12 172.6(3) . . . . ? C9 C10 C11 C16 -6.9(4) . . . . ? C16 C11 C12 C13 0.4(4) . . . . ? C10 C11 C12 C13 -179.1(3) . . . . ? C11 C12 C13 C14 -0.5(4) . . . . ? C12 C13 C14 C15 -0.3(4) . . . . ? C12 C13 C14 N2 179.7(2) . . . . ? C13 C14 C15 C16 1.2(4) . . . . ? N2 C14 C15 C16 -178.8(2) . . . . ? C12 C11 C16 C15 0.5(4) . . . . ? C10 C11 C16 C15 180.0(3) . . . . ? C14 C15 C16 C11 -1.3(4) . . . . ? C17 C18 C19 C24 1.7(4) . . . . ? C17 C18 C19 C20 -179.2(3) . . . . ? C24 C19 C20 C21 0.5(4) . . . . ? C18 C19 C20 C21 -178.7(2) . . . . ? C19 C20 C21 C22 -0.2(4) . . . . ? C20 C21 C22 C23 -0.1(4) . . . . ? C20 C21 C22 N3 -179.1(2) . . . . ? C21 C22 C23 C24 0.2(4) . . . . ? N3 C22 C23 C24 179.2(2) . . . . ? C20 C19 C24 C23 -0.4(4) . . . . ? C18 C19 C24 C23 178.8(3) . . . . ? C22 C23 C24 C19 0.1(4) . . . . ? C25 C26 C27 C32 176.5(3) . . . . ? C25 C26 C27 C28 -3.1(4) . . . . ? C32 C27 C28 C29 0.9(4) . . . . ? C26 C27 C28 C29 -179.5(3) . . . . ? C27 C28 C29 C30 -0.1(4) . . . . ? C28 C29 C30 C31 -0.4(4) . . . . ? C28 C29 C30 N4 179.5(2) . . . . ? C29 C30 C31 C32 0.1(4) . . . . ? N4 C30 C31 C32 -179.9(2) . . . . ? C28 C27 C32 C31 -1.3(4) . . . . ? C26 C27 C32 C31 179.1(2) . . . . ? C30 C31 C32 C27 0.9(4) . . . . ? O2 C33 C34 O3 -0.4(3) . . . . ? O1 C33 C34 O3 178.7(2) . . . . ? O2 C33 C34 C35 -120.9(3) . . . . ? O1 C33 C34 C35 58.2(3) . . . . ? O3 C34 C35 O4 -74.7(2) . . . . ? C33 C34 C35 O4 45.0(3) . . . . ? O3 C34 C35 C36 46.0(3) . . . . ? C33 C34 C35 C36 165.7(2) . . . . ? O4 C35 C36 O5 -2.4(3) . . . . ? C34 C35 C36 O5 -123.5(3) . . . . ? O4 C35 C36 O6 177.7(2) . . . . ? C34 C35 C36 O6 56.6(3) . . . . ? O8 C37 C38 O9 0.4(3) . . . . ? O7 C37 C38 O9 178.8(2) . . . . ? O8 C37 C38 C39 -119.8(3) . . . . ? O7 C37 C38 C39 58.6(3) . . . . ? O9 C38 C39 O10 -73.8(2) . . . . ? C37 C38 C39 O10 46.1(3) . . . . ? O9 C38 C39 C40 47.9(3) . . . . ? C37 C38 C39 C40 167.9(2) . . . . ? O10 C39 C40 O12 -6.6(3) . . . . ? C38 C39 C40 O12 -127.9(3) . . . . ? O10 C39 C40 O11 173.3(2) . . . . ? C38 C39 C40 O11 52.0(3) . . . . ? O14 C41 C42 O15 -2.3(3) . . . . ? O13 C41 C42 O15 178.7(2) . . . . ? O14 C41 C42 C43 -123.2(2) . . . . ? O13 C41 C42 C43 57.8(3) . . . . ? O15 C42 C43 O16 -67.6(3) . . . . ? C41 C42 C43 O16 53.6(3) . . . . ? O15 C42 C43 C44 57.5(3) . . . . ? C41 C42 C43 C44 178.7(2) . . . . ? O16 C43 C44 O17 -162.8(2) . . . . ? C42 C43 C44 O17 73.3(3) . . . . ? O16 C43 C44 O18 20.9(3) . . . . ? C42 C43 C44 O18 -103.0(3) . . . . ? O20 C45 C46 O21 -3.6(3) . . . . ? O19 C45 C46 O21 178.1(2) . . . . ? O20 C45 C46 C47 -124.2(2) . . . . ? O19 C45 C46 C47 57.5(3) . . . . ? O21 C46 C47 O22 -68.4(2) . . . . ? C45 C46 C47 O22 52.9(3) . . . . ? O21 C46 C47 C48 56.1(3) . . . . ? C45 C46 C47 C48 177.4(2) . . . . ? O22 C47 C48 O23 -165.0(2) . . . . ? C46 C47 C48 O23 72.2(3) . . . . ? O22 C47 C48 O24 18.1(3) . . . . ? C46 C47 C48 O24 -104.7(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 N1 H1D O14 0.89 1.84 2.712(3) 165.3 . N1 H1E O19 0.89 1.89 2.775(3) 170.7 . N1 H1F O15 0.89 1.92 2.753(3) 154.6 1_655 N2 H2C O3 0.89 1.98 2.862(3) 174.0 . N2 H2D O7 0.89 2.41 3.260(3) 159.5 1_455 N2 H2D O10 0.89 2.48 2.939(3) 112.6 1_455 N2 H2E O2 0.89 1.89 2.762(3) 165.7 1_455 N3 H3A O9 0.89 2.00 2.883(3) 169.2 . N3 H3B O1 0.89 2.38 3.225(3) 159.3 1_565 N3 H3C O8 0.89 1.87 2.736(3) 165.0 1_455 N4 H4A O20 0.89 1.81 2.679(3) 163.6 1_455 N4 H4B O13 0.89 1.90 2.783(3) 171.6 1_565 N4 H4C O21 0.89 1.94 2.784(3) 157.6 . O3 H3 O2 0.82 2.07 2.580(3) 120.3 . O4 H4D O5 0.82 2.13 2.625(3) 118.9 . O6 H6 O1 0.82 1.78 2.587(3) 167.5 1_455 O9 H9 O8 0.82 2.06 2.573(3) 120.0 . O10 H10 O12 0.82 2.15 2.638(3) 118.1 . O11 H11 O7 0.82 1.78 2.588(3) 170.0 1_455 O15 H15A O14 0.82 2.08 2.578(2) 119.3 . O15 H15A O23 0.82 2.10 2.727(3) 133.7 . O16 H16A O7 0.82 2.05 2.728(3) 140.2 1_456 O18 H18 O13 0.82 1.74 2.551(2) 170.8 1_455 O21 H21A O20 0.82 2.08 2.586(2) 119.3 . O21 H21A O17 0.82 2.09 2.713(3) 132.3 1_665 O22 H22 O1 0.82 2.06 2.739(3) 139.2 1_566 O24 H24A O19 0.82 1.73 2.538(3) 169.8 1_455 O16 H16A O15 0.82 2.58 2.927(2) 107.4 . O22 H22 O21 0.82 2.59 2.922(3) 105.8 . C13 H13 O5 0.93 2.57 3.420(3) 151.9 . C21 H21 O12 0.93 2.52 3.434(3) 165.7 . C25 H25B O8 0.96 2.56 3.455(4) 154.9 1_455 C35 H35 O24 0.98 2.55 3.511(3) 166.0 1_544 C39 H39 O18 0.98 2.53 3.480(3) 162.0 1_654 C43 H43 O6 0.98 2.54 3.274(3) 131.7 1_556 C47 H47 O11 0.98 2.53 3.267(3) 131.8 1_556 _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.245 _refine_diff_density_min -0.219 _refine_diff_density_rms 0.042 #=====================================END data_wudh_RTP(298K) _database_code_depnum_ccdc_archive 'CCDC 773839' #TrackingRef '- 1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C8 H12 N, C4 H5 O6' _chemical_formula_sum 'C12 H17 N O6' _chemical_formula_weight 271.27 _chemical_absolute_configuration syn 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 triclinic _symmetry_space_group_name_H-M 'P 1' _symmetry_space_group_name_Hall 'P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' _cell_length_a 6.0782(12) _cell_length_b 7.4777(15) _cell_length_c 14.9506(10) _cell_angle_alpha 87.655(10) _cell_angle_beta 82.692(10) _cell_angle_gamma 71.8020(10) _cell_volume 640.29(19) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 6505 _cell_measurement_theta_min 3.18 _cell_measurement_theta_max 27.58 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.407 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 288 _exptl_absorpt_coefficient_mu 0.113 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.962 _exptl_absorpt_correction_T_max 0.970 _exptl_absorpt_process_details 'CrystalClear (Rigaku, 2005)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 'Mercury2 (2x2 bin mode)' _diffrn_measurement_method CCD_Profile_fitting _diffrn_detector_area_resol_mean 13.6612 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6591 _diffrn_reflns_av_R_equivalents 0.0357 _diffrn_reflns_av_sigmaI/netI 0.0441 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.18 _diffrn_reflns_theta_max 27.48 _reflns_number_total 2930 _reflns_number_gt 2745 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku, 2005)' _computing_cell_refinement CrystalClear _computing_data_reduction CrystalClear _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material SHELXTL _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^)+(0.0515P)^2^+0.0884P] 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 ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 10(10) _refine_ls_number_reflns 2930 _refine_ls_number_parameters 353 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0440 _refine_ls_R_factor_gt 0.0411 _refine_ls_wR_factor_ref 0.1029 _refine_ls_wR_factor_gt 0.1009 _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_restrained_S_all 1.057 _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 C1 C 0.2847(12) 0.9261(7) -0.1725(3) 0.0881(16) Uani 1 1 d . . . H1A H 0.3648 1.0022 -0.1486 0.132 Uiso 1 1 calc R . . H1B H 0.2844 0.9470 -0.2362 0.132 Uiso 1 1 calc R . . H1C H 0.3626 0.7957 -0.1613 0.132 Uiso 1 1 calc R . . C2 C 0.0428(10) 0.9773(6) -0.1284(2) 0.0726(13) Uani 1 1 d . . . H2A H -0.0318 0.8939 -0.1509 0.087 Uiso 1 1 calc R . . H2B H -0.0384 1.1039 -0.1472 0.087 Uiso 1 1 calc R . . C3 C 0.0069(7) 0.9708(4) -0.0255(2) 0.0479(7) Uani 1 1 d . . . C4 C -0.2129(7) 1.0239(5) 0.0204(2) 0.0549(9) Uani 1 1 d . . . H4 H -0.3398 1.0627 -0.0124 0.066 Uiso 1 1 calc R . . C5 C -0.2547(6) 1.0223(5) 0.1140(2) 0.0497(8) Uani 1 1 d . . . H5 H -0.4061 1.0606 0.1434 0.060 Uiso 1 1 calc R . . C6 C -0.0657(5) 0.9625(3) 0.16228(17) 0.0312(5) Uani 1 1 d . . . C7 C 0.1573(5) 0.9059(4) 0.11893(19) 0.0407(6) Uani 1 1 d . . . H7 H 0.2837 0.8648 0.1519 0.049 Uiso 1 1 calc R . . C8 C 0.1931(6) 0.9105(5) 0.0254(2) 0.0524(8) Uani 1 1 d . . . H8 H 0.3447 0.8725 -0.0038 0.063 Uiso 1 1 calc R . . C9 C -0.2104(14) 0.5209(8) 1.0711(3) 0.108(2) Uani 1 1 d . . . H9A H -0.2871 0.6433 1.0481 0.162 Uiso 1 1 calc R . . H9B H -0.2194 0.5266 1.1355 0.162 Uiso 1 1 calc R . . H9C H -0.2855 0.4332 1.0552 0.162 Uiso 1 1 calc R . . C10 C 0.0358(12) 0.4589(7) 1.0318(3) 0.0851(16) Uani 1 1 d . . . H10A H 0.1072 0.3321 1.0530 0.102 Uiso 1 1 calc R . . H10B H 0.1131 0.5392 1.0554 0.102 Uiso 1 1 calc R . . C11 C 0.0853(8) 0.4591(5) 0.9292(2) 0.0559(9) Uani 1 1 d . . . C12 C 0.3116(8) 0.4050(5) 0.8883(3) 0.0634(10) Uani 1 1 d . . . H12 H 0.4326 0.3707 0.9242 0.076 Uiso 1 1 calc R . . C13 C 0.3655(6) 0.3998(5) 0.7955(3) 0.0529(8) Uani 1 1 d . . . H13 H 0.5201 0.3614 0.7694 0.064 Uiso 1 1 calc R . . C14 C 0.1862(5) 0.4526(3) 0.74246(19) 0.0332(5) Uani 1 1 d . . . C15 C -0.0408(6) 0.5099(5) 0.7810(2) 0.0498(8) Uani 1 1 d . . . H15 H -0.1615 0.5463 0.7451 0.060 Uiso 1 1 calc R . . C16 C -0.0894(7) 0.5132(6) 0.8742(3) 0.0617(9) Uani 1 1 d . . . H16 H -0.2440 0.5531 0.9003 0.074 Uiso 1 1 calc R . . C17 C 0.2676(4) 0.2520(4) 0.32530(18) 0.0309(5) Uani 1 1 d . . . C18 C 0.2579(4) 0.4566(3) 0.33387(18) 0.0310(5) Uani 1 1 d . . . H18 H 0.1311 0.5169 0.3807 0.037 Uiso 1 1 calc R . . C19 C 0.4855(4) 0.4721(3) 0.36007(17) 0.0283(5) Uani 1 1 d . . . H19 H 0.4967 0.4360 0.4235 0.034 Uiso 1 1 calc R . . C20 C 0.4915(5) 0.6766(3) 0.34720(18) 0.0307(5) Uani 1 1 d . . . C21 C 0.6698(4) 0.7473(3) 0.55796(16) 0.0248(4) Uani 1 1 d . . . C22 C 0.7182(4) 0.9332(3) 0.53335(16) 0.0250(5) Uani 1 1 d . . . H22 H 0.5684 1.0306 0.5292 0.030 Uiso 1 1 calc R . . C23 C 0.8264(4) 0.9828(3) 0.61237(17) 0.0258(5) Uani 1 1 d . . . H23 H 0.7156 0.9950 0.6672 0.031 Uiso 1 1 calc R . . C24 C 0.8805(4) 1.1684(3) 0.59561(17) 0.0278(5) Uani 1 1 d . . . N1 N -0.1064(4) 0.9580(3) 0.26089(14) 0.0329(5) Uani 1 1 d . . . H1D H -0.1702 1.0749 0.2818 0.049 Uiso 1 1 calc R . . H1E H 0.0287 0.9056 0.2828 0.049 Uiso 1 1 calc R . . H1F H -0.2023 0.8909 0.2780 0.049 Uiso 1 1 calc R . . N2 N 0.2366(4) 0.4484(3) 0.64435(15) 0.0309(5) Uani 1 1 d . . . H2C H 0.1768 0.3676 0.6221 0.046 Uiso 1 1 calc R . . H2D H 0.3903 0.4122 0.6288 0.046 Uiso 1 1 calc R . . H2E H 0.1735 0.5628 0.6223 0.046 Uiso 1 1 calc R . . O1 O 0.2220(5) 0.1955(3) 0.25778(17) 0.0564(6) Uani 1 1 d . . . O2 O 0.3279(4) 0.1499(3) 0.39565(15) 0.0471(5) Uani 1 1 d . . . H2 H 0.3409 0.0400 0.3854 0.071 Uiso 1 1 calc R . . O3 O 0.2115(4) 0.5514(3) 0.25158(17) 0.0504(6) Uani 1 1 d . . . H3 H 0.1819 0.4823 0.2169 0.076 Uiso 1 1 calc R . . O4 O 0.6769(3) 0.3499(3) 0.30563(16) 0.0426(5) Uani 1 1 d . . . H4A H 0.7626 0.4092 0.2826 0.064 Uiso 1 1 calc R . . O5 O 0.3284(4) 0.8027(3) 0.38956(18) 0.0519(6) Uani 1 1 d . . . O6 O 0.6564(4) 0.6996(3) 0.29634(15) 0.0436(5) Uani 1 1 d . . . O7 O 0.8197(3) 0.5991(2) 0.51740(14) 0.0354(4) Uani 1 1 d . . . H7A H 0.7774 0.5064 0.5305 0.053 Uiso 1 1 calc R . . O8 O 0.5112(3) 0.7413(3) 0.61440(14) 0.0392(5) Uani 1 1 d . . . O9 O 0.8595(3) 0.9289(3) 0.45133(12) 0.0348(4) Uani 1 1 d . . . H9 H 0.9944 0.8670 0.4573 0.052 Uiso 1 1 calc R . . O10 O 1.0324(3) 0.8358(2) 0.62475(15) 0.0371(4) Uani 1 1 d . . . H10 H 1.1436 0.8770 0.6183 0.056 Uiso 1 1 calc R . . O11 O 0.7116(3) 1.3112(2) 0.58058(17) 0.0414(5) Uani 1 1 d . . . O12 O 1.0827(3) 1.1654(3) 0.59969(15) 0.0390(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.150(5) 0.084(3) 0.0334(18) -0.0046(19) 0.015(2) -0.051(3) C2 0.130(4) 0.067(2) 0.0331(16) 0.0037(16) -0.012(2) -0.047(3) C3 0.079(2) 0.0382(15) 0.0318(14) 0.0040(11) -0.0093(14) -0.0253(15) C4 0.065(2) 0.056(2) 0.0471(18) 0.0105(15) -0.0262(16) -0.0179(17) C5 0.0388(16) 0.058(2) 0.0488(17) 0.0039(15) -0.0067(13) -0.0094(14) C6 0.0416(14) 0.0254(11) 0.0290(12) 0.0019(9) -0.0036(10) -0.0144(10) C7 0.0398(15) 0.0482(17) 0.0330(14) -0.0026(12) 0.0000(11) -0.0136(13) C8 0.057(2) 0.062(2) 0.0364(16) -0.0033(14) 0.0070(14) -0.0213(17) C9 0.190(7) 0.087(4) 0.041(2) -0.004(2) 0.013(3) -0.046(4) C10 0.166(5) 0.065(3) 0.042(2) 0.0091(18) -0.028(3) -0.056(3) C11 0.099(3) 0.0397(16) 0.0405(17) 0.0073(13) -0.0212(18) -0.0331(18) C12 0.082(3) 0.056(2) 0.059(2) 0.0097(17) -0.041(2) -0.019(2) C13 0.0487(18) 0.0524(19) 0.059(2) 0.0046(15) -0.0246(15) -0.0104(15) C14 0.0402(14) 0.0229(11) 0.0395(14) 0.0050(10) -0.0108(11) -0.0124(10) C15 0.0454(17) 0.061(2) 0.0430(17) 0.0068(15) -0.0113(13) -0.0158(15) C16 0.066(2) 0.071(2) 0.0470(19) 0.0024(17) -0.0003(16) -0.0220(19) C17 0.0246(11) 0.0304(12) 0.0377(13) -0.0024(10) -0.0002(9) -0.0097(10) C18 0.0288(12) 0.0243(11) 0.0381(13) 0.0018(10) -0.0039(10) -0.0059(9) C19 0.0328(12) 0.0210(11) 0.0314(12) 0.0009(9) -0.0024(9) -0.0095(9) C20 0.0349(13) 0.0234(11) 0.0360(13) 0.0006(10) -0.0017(10) -0.0134(10) C21 0.0218(10) 0.0203(10) 0.0327(12) 0.0011(9) -0.0055(9) -0.0064(8) C22 0.0248(11) 0.0190(10) 0.0319(12) 0.0022(8) -0.0050(9) -0.0074(8) C23 0.0284(11) 0.0175(10) 0.0326(11) 0.0018(8) -0.0052(9) -0.0081(9) C24 0.0356(13) 0.0168(10) 0.0321(12) -0.0032(8) -0.0008(10) -0.0105(9) N1 0.0400(12) 0.0287(10) 0.0302(11) 0.0010(8) 0.0020(9) -0.0136(9) N2 0.0300(11) 0.0237(10) 0.0403(12) 0.0028(8) -0.0074(9) -0.0093(8) O1 0.0782(17) 0.0503(13) 0.0527(14) -0.0018(10) -0.0215(12) -0.0319(12) O2 0.0740(15) 0.0274(10) 0.0484(12) 0.0067(9) -0.0188(11) -0.0243(10) O3 0.0541(13) 0.0413(12) 0.0593(14) 0.0183(10) -0.0263(11) -0.0143(10) O4 0.0321(10) 0.0254(9) 0.0648(14) -0.0026(9) 0.0048(9) -0.0048(7) O5 0.0524(13) 0.0208(9) 0.0773(16) -0.0069(9) 0.0202(11) -0.0139(9) O6 0.0490(12) 0.0353(10) 0.0503(12) -0.0044(9) 0.0111(9) -0.0246(9) O7 0.0362(10) 0.0200(8) 0.0474(11) -0.0035(7) 0.0074(8) -0.0092(7) O8 0.0356(10) 0.0288(9) 0.0513(12) 0.0001(8) 0.0076(9) -0.0124(8) O9 0.0412(10) 0.0336(9) 0.0295(9) 0.0069(7) -0.0032(7) -0.0130(8) O10 0.0362(10) 0.0190(8) 0.0603(12) 0.0112(8) -0.0228(9) -0.0094(7) O11 0.0314(9) 0.0162(8) 0.0736(14) 0.0044(8) -0.0037(9) -0.0050(7) O12 0.0357(10) 0.0249(8) 0.0615(13) 0.0013(8) -0.0102(9) -0.0149(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 C1 C2 1.472(8) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 C3 1.527(4) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.368(6) . ? C3 C8 1.391(5) . ? C4 C5 1.391(5) . ? C4 H4 0.9300 . ? C5 C6 1.380(4) . ? C5 H5 0.9300 . ? C6 C7 1.370(4) . ? C6 N1 1.464(3) . ? C7 C8 1.388(4) . ? C7 H7 0.9300 . ? C8 H8 0.9300 . ? C9 C10 1.471(10) . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 C11 1.525(5) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.375(6) . ? C11 C16 1.376(6) . ? C12 C13 1.384(6) . ? C12 H12 0.9300 . ? C13 C14 1.378(4) . ? C13 H13 0.9300 . ? C14 C15 1.367(4) . ? C14 N2 1.459(4) . ? C15 C16 1.387(5) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? C17 O1 1.206(4) . ? C17 O2 1.296(3) . ? C17 C18 1.523(3) . ? C18 O3 1.410(3) . ? C18 C19 1.524(3) . ? C18 H18 0.9800 . ? C19 O4 1.416(3) . ? C19 C20 1.545(3) . ? C19 H19 0.9800 . ? C20 O6 1.231(3) . ? C20 O5 1.256(3) . ? C21 O8 1.209(3) . ? C21 O7 1.308(3) . ? C21 C22 1.529(3) . ? C22 O9 1.400(3) . ? C22 C23 1.534(3) . ? C22 H22 0.9800 . ? C23 O10 1.412(3) . ? C23 C24 1.527(3) . ? C23 H23 0.9800 . ? C24 O12 1.232(3) . ? C24 O11 1.265(3) . ? N1 H1D 0.8900 . ? N1 H1E 0.8900 . ? N1 H1F 0.8900 . ? N2 H2C 0.8900 . ? N2 H2D 0.8900 . ? N2 H2E 0.8900 . ? O2 H2 0.8200 . ? O3 H3 0.8200 . ? O4 H4A 0.8200 . ? O7 H7A 0.8200 . ? O9 H9 0.8200 . ? O10 H10 0.8200 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C1 C2 C3 117.2(4) . . ? C1 C2 H2A 108.0 . . ? C3 C2 H2A 108.0 . . ? C1 C2 H2B 108.0 . . ? C3 C2 H2B 108.0 . . ? H2A C2 H2B 107.2 . . ? C4 C3 C8 117.2(3) . . ? C4 C3 C2 120.6(4) . . ? C8 C3 C2 122.1(4) . . ? C3 C4 C5 122.8(3) . . ? C3 C4 H4 118.6 . . ? C5 C4 H4 118.6 . . ? C6 C5 C4 118.3(3) . . ? C6 C5 H5 120.8 . . ? C4 C5 H5 120.8 . . ? C7 C6 C5 120.7(3) . . ? C7 C6 N1 120.2(2) . . ? C5 C6 N1 119.1(3) . . ? C6 C7 C8 119.5(3) . . ? C6 C7 H7 120.2 . . ? C8 C7 H7 120.2 . . ? C7 C8 C3 121.4(3) . . ? C7 C8 H8 119.3 . . ? C3 C8 H8 119.3 . . ? C10 C9 H9A 109.5 . . ? C10 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C10 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C9 C10 C11 117.1(5) . . ? 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 . . ? C12 C11 C16 117.4(3) . . ? C12 C11 C10 120.0(4) . . ? C16 C11 C10 122.6(4) . . ? C11 C12 C13 122.2(3) . . ? C11 C12 H12 118.9 . . ? C13 C12 H12 118.9 . . ? C14 C13 C12 118.8(4) . . ? C14 C13 H13 120.6 . . ? C12 C13 H13 120.6 . . ? C15 C14 C13 120.5(3) . . ? C15 C14 N2 119.2(2) . . ? C13 C14 N2 120.3(3) . . ? C14 C15 C16 119.4(3) . . ? C14 C15 H15 120.3 . . ? C16 C15 H15 120.3 . . ? C11 C16 C15 121.7(4) . . ? C11 C16 H16 119.2 . . ? C15 C16 H16 119.2 . . ? O1 C17 O2 124.9(3) . . ? O1 C17 C18 121.0(3) . . ? O2 C17 C18 114.1(2) . . ? O3 C18 C17 109.8(2) . . ? O3 C18 C19 109.6(2) . . ? C17 C18 C19 111.47(19) . . ? O3 C18 H18 108.6 . . ? C17 C18 H18 108.6 . . ? C19 C18 H18 108.6 . . ? O4 C19 C18 109.7(2) . . ? O4 C19 C20 109.5(2) . . ? C18 C19 C20 110.0(2) . . ? O4 C19 H19 109.2 . . ? C18 C19 H19 109.2 . . ? C20 C19 H19 109.2 . . ? O6 C20 O5 126.5(2) . . ? O6 C20 C19 116.5(2) . . ? O5 C20 C19 117.0(2) . . ? O8 C21 O7 124.0(2) . . ? O8 C21 C22 121.1(2) . . ? O7 C21 C22 114.8(2) . . ? O9 C22 C21 114.08(19) . . ? O9 C22 C23 111.77(19) . . ? C21 C22 C23 106.58(19) . . ? O9 C22 H22 108.1 . . ? C21 C22 H22 108.1 . . ? C23 C22 H22 108.1 . . ? O10 C23 C24 110.09(19) . . ? O10 C23 C22 109.04(19) . . ? C24 C23 C22 111.29(19) . . ? O10 C23 H23 108.8 . . ? C24 C23 H23 108.8 . . ? C22 C23 H23 108.8 . . ? O12 C24 O11 126.3(2) . . ? O12 C24 C23 117.1(2) . . ? O11 C24 C23 116.6(2) . . ? C6 N1 H1D 109.5 . . ? C6 N1 H1E 109.5 . . ? H1D N1 H1E 109.5 . . ? C6 N1 H1F 109.5 . . ? H1D N1 H1F 109.5 . . ? H1E N1 H1F 109.5 . . ? C14 N2 H2C 109.5 . . ? C14 N2 H2D 109.5 . . ? H2C N2 H2D 109.5 . . ? C14 N2 H2E 109.5 . . ? H2C N2 H2E 109.5 . . ? H2D N2 H2E 109.5 . . ? C17 O2 H2 109.5 . . ? C18 O3 H3 109.5 . . ? C19 O4 H4A 109.5 . . ? C21 O7 H7A 109.5 . . ? C22 O9 H9 109.5 . . ? C23 O10 H10 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 C1 C2 C3 C4 177.3(4) . . . . ? C1 C2 C3 C8 -3.1(5) . . . . ? C8 C3 C4 C5 1.0(5) . . . . ? C2 C3 C4 C5 -179.3(3) . . . . ? C3 C4 C5 C6 -0.8(5) . . . . ? C4 C5 C6 C7 -0.1(5) . . . . ? C4 C5 C6 N1 -179.4(3) . . . . ? C5 C6 C7 C8 0.5(5) . . . . ? N1 C6 C7 C8 179.9(3) . . . . ? C6 C7 C8 C3 -0.2(5) . . . . ? C4 C3 C8 C7 -0.5(5) . . . . ? C2 C3 C8 C7 179.9(3) . . . . ? C9 C10 C11 C12 179.2(4) . . . . ? C9 C10 C11 C16 -0.3(6) . . . . ? C16 C11 C12 C13 -1.5(6) . . . . ? C10 C11 C12 C13 178.9(3) . . . . ? C11 C12 C13 C14 0.7(6) . . . . ? C12 C13 C14 C15 0.3(5) . . . . ? C12 C13 C14 N2 -179.8(3) . . . . ? C13 C14 C15 C16 -0.4(5) . . . . ? N2 C14 C15 C16 179.7(3) . . . . ? C12 C11 C16 C15 1.4(6) . . . . ? C10 C11 C16 C15 -179.1(4) . . . . ? C14 C15 C16 C11 -0.4(6) . . . . ? O1 C17 C18 O3 -5.1(4) . . . . ? O2 C17 C18 O3 174.8(2) . . . . ? O1 C17 C18 C19 -126.8(3) . . . . ? O2 C17 C18 C19 53.2(3) . . . . ? O3 C18 C19 O4 -75.0(3) . . . . ? C17 C18 C19 O4 46.7(3) . . . . ? O3 C18 C19 C20 45.5(3) . . . . ? C17 C18 C19 C20 167.2(2) . . . . ? O4 C19 C20 O6 -1.9(3) . . . . ? C18 C19 C20 O6 -122.5(3) . . . . ? O4 C19 C20 O5 178.2(2) . . . . ? C18 C19 C20 O5 57.6(3) . . . . ? O8 C21 C22 O9 -162.8(2) . . . . ? O7 C21 C22 O9 21.0(3) . . . . ? O8 C21 C22 C23 73.4(3) . . . . ? O7 C21 C22 C23 -102.8(2) . . . . ? O9 C22 C23 O10 -66.4(2) . . . . ? C21 C22 C23 O10 58.9(2) . . . . ? O9 C22 C23 C24 55.3(3) . . . . ? C21 C22 C23 C24 -179.47(18) . . . . ? O10 C23 C24 O12 -3.5(3) . . . . ? C22 C23 C24 O12 -124.5(2) . . . . ? O10 C23 C24 O11 177.9(2) . . . . ? C22 C23 C24 O11 56.8(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 N1 H1D O4 0.89 2.00 2.880(3) 169.6 1_465 N1 H1E O5 0.89 2.49 3.350(4) 161.6 . N1 H1E O3 0.89 2.57 3.048(3) 114.6 . N1 H1F O6 0.89 1.88 2.749(3) 164.9 1_455 N2 H2C O12 0.89 1.83 2.704(3) 165.8 1_445 N2 H2D O11 0.89 1.92 2.798(3) 170.8 1_545 N2 H2E O10 0.89 1.95 2.792(3) 156.9 1_455 O2 H2 O5 0.82 1.80 2.601(3) 165.9 1_545 O3 H3 O1 0.82 2.15 2.640(3) 118.1 . O4 H4A O6 0.82 2.07 2.578(3) 119.4 . O7 H7A O11 0.82 1.75 2.553(3) 167.5 1_545 O9 H9 O5 0.82 2.07 2.755(3) 140.8 1_655 O10 H10 O12 0.82 2.08 2.583(2) 119.0 . O10 H10 O8 0.82 2.14 2.757(3) 132.1 1_655 O9 H9 O10 0.82 2.54 2.898(3) 108.0 . C18 H18 O7 0.98 2.55 3.517(3) 167.1 1_455 C22 H22 O2 0.98 2.59 3.326(3) 132.1 1_565 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.235 _refine_diff_density_min -0.194 _refine_diff_density_rms 0.043 #===END data_wudh_HTP(373K) _database_code_depnum_ccdc_archive 'CCDC 773840' #TrackingRef '- 1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C8 H12 N, C4 H5 O6' _chemical_formula_sum 'C12 H17 N O6' _chemical_formula_weight 271.27 _chemical_absolute_configuration syn 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 triclinic _symmetry_space_group_name_H-M 'P 1' _symmetry_space_group_name_Hall 'P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' _cell_length_a 6.1181(17) _cell_length_b 7.4980(10) _cell_length_c 15.0901(14) _cell_angle_alpha 87.224(2) _cell_angle_beta 82.128(2) _cell_angle_gamma 71.9900(10) _cell_volume 652.1(2) _cell_formula_units_Z 2 _cell_measurement_temperature 373(2) _cell_measurement_reflns_used 1818 _cell_measurement_theta_min 3.53 _cell_measurement_theta_max 27.45 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.382 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 288 _exptl_absorpt_coefficient_mu 0.111 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.962 _exptl_absorpt_correction_T_max 0.970 _exptl_absorpt_process_details 'CrystalClear (Rigaku, 2005)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 373(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 'Mercury2 (2x2 bin mode)' _diffrn_measurement_method CCD_Profile_fitting _diffrn_detector_area_resol_mean 13.6612 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7125 _diffrn_reflns_av_R_equivalents 0.0325 _diffrn_reflns_av_sigmaI/netI 0.0422 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.86 _diffrn_reflns_theta_max 27.43 _reflns_number_total 2942 _reflns_number_gt 2280 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku, 2005)' _computing_cell_refinement CrystalClear _computing_data_reduction CrystalClear _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material SHELXTL _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^)+(0.0496P)^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 ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -10(10) _refine_ls_number_reflns 2942 _refine_ls_number_parameters 353 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0605 _refine_ls_R_factor_gt 0.0452 _refine_ls_wR_factor_ref 0.1013 _refine_ls_wR_factor_gt 0.0945 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.034 _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 C1 C 0.4037(19) 0.9929(10) 0.7960(4) 0.156(4) Uani 1 1 d . . . H1A H 0.3315 1.1216 0.7808 0.235 Uiso 1 1 calc R . . H1B H 0.3995 0.9803 0.8598 0.235 Uiso 1 1 calc R . . H1C H 0.3221 0.9160 0.7751 0.235 Uiso 1 1 calc R . . C2 C 0.6391(13) 0.9347(8) 0.7549(3) 0.108(2) Uani 1 1 d . . . H2A H 0.7108 0.8078 0.7751 0.130 Uiso 1 1 calc R . . H2B H 0.7175 1.0138 0.7777 0.130 Uiso 1 1 calc R . . C3 C 0.6882(11) 0.9372(6) 0.6523(3) 0.0715(12) Uani 1 1 d . . . C4 C 0.9090(10) 0.8830(7) 0.6107(3) 0.0800(14) Uani 1 1 d . . . H4 H 1.0295 0.8458 0.6457 0.096 Uiso 1 1 calc R . . C5 C 0.9635(8) 0.8805(6) 0.5185(3) 0.0666(11) Uani 1 1 d . . . H5 H 1.1172 0.8440 0.4923 0.080 Uiso 1 1 calc R . . C6 C 0.7870(6) 0.9329(4) 0.4666(2) 0.0439(8) Uani 1 1 d . . . C7 C 0.5597(7) 0.9915(6) 0.5056(3) 0.0616(11) Uani 1 1 d . . . H7 H 0.4394 1.0300 0.4706 0.074 Uiso 1 1 calc R . . C8 C 0.5139(9) 0.9920(7) 0.5988(3) 0.0776(13) Uani 1 1 d . . . H8 H 0.3607 1.0306 0.6256 0.093 Uiso 1 1 calc R . . C9 C 0.8823(14) 0.4077(9) 0.5528(4) 0.124(3) Uani 1 1 d . . . H9A H 0.9657 0.4788 0.5774 0.186 Uiso 1 1 calc R . . H9B H 0.8801 0.4350 0.4900 0.186 Uiso 1 1 calc R . . H9C H 0.9572 0.2763 0.5611 0.186 Uiso 1 1 calc R . . C10 C 0.6449(12) 0.4580(8) 0.5981(3) 0.0951(18) Uani 1 1 d . . . H10A H 0.5691 0.3759 0.5762 0.114 Uiso 1 1 calc R . . H10B H 0.5648 0.5847 0.5799 0.114 Uiso 1 1 calc R . . C11 C 0.6100(9) 0.4498(6) 0.7002(3) 0.0630(11) Uani 1 1 d . . . C12 C 0.3922(8) 0.5043(6) 0.7458(3) 0.0684(12) Uani 1 1 d . . . H12 H 0.2665 0.5460 0.7135 0.082 Uiso 1 1 calc R . . C13 C 0.3497(7) 0.5000(6) 0.8394(3) 0.0613(11) Uani 1 1 d . . . H13 H 0.1988 0.5369 0.8686 0.074 Uiso 1 1 calc R . . C14 C 0.5356(6) 0.4402(4) 0.8875(2) 0.0395(7) Uani 1 1 d . . . C15 C 0.7566(6) 0.3839(5) 0.8442(2) 0.0523(9) Uani 1 1 d . . . H15 H 0.8822 0.3422 0.8765 0.063 Uiso 1 1 calc R . . C16 C 0.7916(8) 0.3896(6) 0.7513(3) 0.0679(12) Uani 1 1 d . . . H16 H 0.9426 0.3516 0.7222 0.082 Uiso 1 1 calc R . . C17 C 0.0932(6) 1.1518(4) 0.0716(2) 0.0414(8) Uani 1 1 d . . . C18 C 0.0865(5) 0.9480(4) 0.0837(2) 0.0373(7) Uani 1 1 d . . . H18 H 0.1014 0.9096 0.1461 0.045 Uiso 1 1 calc R . . C19 C -0.1409(6) 0.9316(4) 0.0604(2) 0.0427(8) Uani 1 1 d . . . H19 H -0.2649 0.9901 0.1081 0.051 Uiso 1 1 calc R . . C20 C -0.1320(5) 0.7282(4) 0.0516(2) 0.0417(8) Uani 1 1 d . . . C21 C 0.4787(6) 0.6515(4) 0.3196(2) 0.0371(7) Uani 1 1 d . . . C22 C 0.4267(5) 0.4655(4) 0.3358(2) 0.0346(7) Uani 1 1 d . . . H22 H 0.3162 0.4761 0.3903 0.042 Uiso 1 1 calc R . . C23 C 0.3221(5) 0.4137(4) 0.2585(2) 0.0340(7) Uani 1 1 d . . . H23 H 0.1738 0.5105 0.2540 0.041 Uiso 1 1 calc R . . C24 C 0.2716(5) 0.2294(4) 0.2831(2) 0.0342(7) Uani 1 1 d . . . N1 N 0.8371(4) 0.9314(4) 0.36898(18) 0.0404(6) Uani 1 1 d . . . H1D H 0.7764 0.8523 0.3468 0.061 Uiso 1 1 calc R . . H1E H 0.9898 0.8950 0.3531 0.061 Uiso 1 1 calc R . . H1F H 0.7756 1.0462 0.3476 0.061 Uiso 1 1 calc R . . N2 N 0.4928(5) 0.4365(4) 0.98568(17) 0.0434(7) Uani 1 1 d . . . H2C H 0.4234 0.5526 1.0058 0.065 Uiso 1 1 calc R . . H2D H 0.6270 0.3895 1.0076 0.065 Uiso 1 1 calc R . . H2E H 0.4021 0.3653 1.0031 0.065 Uiso 1 1 calc R . . O1 O -0.0660(4) 1.2759(3) 0.1153(2) 0.0673(8) Uani 1 1 d . . . O2 O 0.2564(4) 1.1762(3) 0.02012(18) 0.0591(7) Uani 1 1 d . . . O3 O 0.2748(4) 0.8278(3) 0.0275(2) 0.0574(7) Uani 1 1 d . . . H3 H 0.3520 0.8897 0.0001 0.086 Uiso 1 1 calc R . . O4 O -0.1918(6) 1.0280(4) -0.0205(2) 0.0706(8) Uani 1 1 d . . . H4A H -0.2125 0.9569 -0.0558 0.106 Uiso 1 1 calc R . . O5 O -0.0655(5) 0.6239(3) 0.11991(18) 0.0623(7) Uani 1 1 d . . . H5A H -0.0647 0.5166 0.1114 0.093 Uiso 1 1 calc R . . O6 O -0.1806(6) 0.6729(4) -0.0145(2) 0.0766(9) Uani 1 1 d . . . O7 O 0.6787(4) 0.6507(3) 0.32389(18) 0.0506(6) Uani 1 1 d . . . O8 O 0.3105(4) 0.7922(3) 0.30443(19) 0.0525(6) Uani 1 1 d . . . O9 O 0.6325(4) 0.3192(3) 0.34813(18) 0.0494(6) Uani 1 1 d . . . H9 H 0.7386 0.3638 0.3497 0.074 Uiso 1 1 calc R . . O10 O 0.4643(4) 0.4090(3) 0.17599(15) 0.0445(5) Uani 1 1 d . . . H10 H 0.6008 0.3634 0.1836 0.067 Uiso 1 1 calc R . . O11 O 0.4192(4) 0.0811(3) 0.24299(18) 0.0476(6) Uani 1 1 d . . . H11 H 0.3795 -0.0117 0.2586 0.071 Uiso 1 1 calc R . . O12 O 0.1124(4) 0.2230(3) 0.33910(17) 0.0516(6) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.295(12) 0.115(6) 0.061(4) -0.009(4) 0.023(5) -0.084(7) C2 0.201(7) 0.087(4) 0.054(3) 0.001(3) -0.011(4) -0.071(4) C3 0.122(4) 0.051(2) 0.053(3) 0.0059(19) -0.022(3) -0.041(3) C4 0.105(4) 0.070(3) 0.076(3) 0.013(2) -0.051(3) -0.029(3) C5 0.062(2) 0.070(3) 0.070(3) 0.003(2) -0.026(2) -0.017(2) C6 0.052(2) 0.0333(17) 0.052(2) 0.0039(14) -0.0117(17) -0.0191(15) C7 0.056(2) 0.072(3) 0.058(3) 0.006(2) -0.012(2) -0.021(2) C8 0.087(3) 0.085(3) 0.059(3) -0.003(2) 0.010(3) -0.032(3) C9 0.207(7) 0.124(5) 0.049(3) -0.013(3) 0.025(4) -0.076(5) C10 0.168(6) 0.083(3) 0.049(3) 0.000(2) -0.005(3) -0.063(4) C11 0.100(3) 0.052(2) 0.044(2) 0.0028(17) -0.012(2) -0.033(2) C12 0.081(3) 0.071(3) 0.056(3) 0.013(2) -0.029(2) -0.021(2) C13 0.051(2) 0.065(3) 0.064(3) 0.007(2) -0.005(2) -0.014(2) C14 0.0501(19) 0.0313(15) 0.0396(18) -0.0010(13) -0.0019(15) -0.0174(15) C15 0.052(2) 0.061(2) 0.042(2) -0.0041(17) 0.0012(17) -0.0166(19) C16 0.078(3) 0.075(3) 0.046(2) -0.008(2) 0.014(2) -0.025(2) C17 0.0459(18) 0.0324(16) 0.049(2) -0.0002(14) -0.0030(16) -0.0172(15) C18 0.0407(16) 0.0290(15) 0.0412(18) 0.0015(13) -0.0030(13) -0.0103(13) C19 0.0375(17) 0.0309(15) 0.058(2) -0.0013(14) -0.0017(15) -0.0094(14) C20 0.0353(16) 0.0366(17) 0.054(2) -0.0054(15) -0.0019(15) -0.0125(14) C21 0.0432(18) 0.0244(14) 0.0451(18) -0.0047(12) -0.0013(14) -0.0136(14) C22 0.0369(16) 0.0247(14) 0.0431(17) 0.0001(12) -0.0029(13) -0.0118(13) C23 0.0347(15) 0.0244(14) 0.0433(18) 0.0014(12) -0.0049(13) -0.0097(12) C24 0.0323(15) 0.0284(15) 0.0426(18) -0.0013(12) -0.0074(14) -0.0087(13) N1 0.0405(15) 0.0311(13) 0.0523(17) 0.0033(12) -0.0078(13) -0.0147(12) N2 0.0523(17) 0.0371(15) 0.0399(16) -0.0007(12) 0.0027(13) -0.0160(13) O1 0.0653(17) 0.0299(13) 0.101(2) -0.0124(13) 0.0276(16) -0.0210(13) O2 0.0653(16) 0.0462(14) 0.0699(19) -0.0081(12) 0.0175(14) -0.0331(13) O3 0.0425(13) 0.0343(13) 0.087(2) -0.0088(12) 0.0126(13) -0.0067(11) O4 0.0744(18) 0.0545(17) 0.089(2) 0.0265(15) -0.0406(17) -0.0205(15) O5 0.095(2) 0.0377(13) 0.0672(18) 0.0081(12) -0.0231(16) -0.0342(15) O6 0.104(2) 0.0653(18) 0.079(2) -0.0049(15) -0.0309(18) -0.0434(18) O7 0.0455(13) 0.0325(12) 0.0806(17) -0.0014(11) -0.0134(12) -0.0192(11) O8 0.0422(12) 0.0228(11) 0.0896(19) 0.0013(10) -0.0033(12) -0.0083(10) O9 0.0483(13) 0.0260(11) 0.0798(17) 0.0114(11) -0.0283(13) -0.0128(10) O10 0.0515(13) 0.0438(13) 0.0399(13) 0.0075(9) -0.0036(10) -0.0193(12) O11 0.0501(14) 0.0270(11) 0.0626(15) -0.0054(10) 0.0097(12) -0.0136(11) O12 0.0456(13) 0.0383(13) 0.0689(17) -0.0025(11) 0.0125(12) -0.0181(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.429(11) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 C3 1.536(7) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.356(7) . ? C3 C8 1.375(7) . ? C4 C5 1.385(7) . ? C4 H4 0.9300 . ? C5 C6 1.368(5) . ? C5 H5 0.9300 . ? C6 C7 1.377(5) . ? C6 N1 1.464(4) . ? C7 C8 1.396(6) . ? C7 H7 0.9300 . ? C8 H8 0.9300 . ? C9 C10 1.461(10) . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 C11 1.527(6) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.362(7) . ? C11 C16 1.387(6) . ? C12 C13 1.401(6) . ? C12 H12 0.9300 . ? C13 C14 1.379(5) . ? C13 H13 0.9300 . ? C14 C15 1.366(5) . ? C14 N2 1.469(4) . ? C15 C16 1.389(6) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? C17 O2 1.233(4) . ? C17 O1 1.253(4) . ? C17 C18 1.543(4) . ? C18 O3 1.422(4) . ? C18 C19 1.523(4) . ? C18 H18 0.9800 . ? C19 O4 1.410(4) . ? C19 C20 1.521(4) . ? C19 H19 0.9800 . ? C20 O6 1.205(4) . ? C20 O5 1.296(4) . ? C21 O7 1.232(4) . ? C21 O8 1.263(4) . ? C21 C22 1.525(4) . ? C22 O9 1.419(4) . ? C22 C23 1.523(4) . ? C22 H22 0.9800 . ? C23 O10 1.414(4) . ? C23 C24 1.525(4) . ? C23 H23 0.9800 . ? C24 O12 1.210(4) . ? C24 O11 1.309(4) . ? N1 H1D 0.8900 . ? N1 H1E 0.8900 . ? N1 H1F 0.8900 . ? N2 H2C 0.8900 . ? N2 H2D 0.8900 . ? N2 H2E 0.8900 . ? O3 H3 0.8200 . ? O4 H4A 0.8200 . ? O5 H5A 0.8200 . ? O9 H9 0.8200 . ? O10 H10 0.8200 . ? O11 H11 0.8200 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C1 C2 C3 118.7(6) . . ? C1 C2 H2A 107.6 . . ? C3 C2 H2A 107.6 . . ? C1 C2 H2B 107.6 . . ? C3 C2 H2B 107.6 . . ? H2A C2 H2B 107.1 . . ? C4 C3 C8 117.1(4) . . ? C4 C3 C2 120.5(5) . . ? C8 C3 C2 122.4(5) . . ? C3 C4 C5 123.0(5) . . ? C3 C4 H4 118.5 . . ? C5 C4 H4 118.5 . . ? C6 C5 C4 118.8(4) . . ? C6 C5 H5 120.6 . . ? C4 C5 H5 120.6 . . ? C5 C6 C7 120.5(4) . . ? C5 C6 N1 120.5(3) . . ? C7 C6 N1 119.0(3) . . ? C6 C7 C8 118.5(4) . . ? C6 C7 H7 120.7 . . ? C8 C7 H7 120.7 . . ? C3 C8 C7 122.1(5) . . ? C3 C8 H8 119.0 . . ? C7 C8 H8 119.0 . . ? C10 C9 H9A 109.5 . . ? C10 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C10 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C9 C10 C11 117.9(6) . . ? C9 C10 H10A 107.8 . . ? C11 C10 H10A 107.8 . . ? C9 C10 H10B 107.8 . . ? C11 C10 H10B 107.8 . . ? H10A C10 H10B 107.2 . . ? C12 C11 C16 116.5(4) . . ? C12 C11 C10 120.2(5) . . ? C16 C11 C10 123.3(5) . . ? C11 C12 C13 122.7(4) . . ? C11 C12 H12 118.7 . . ? C13 C12 H12 118.7 . . ? C14 C13 C12 118.8(4) . . ? C14 C13 H13 120.6 . . ? C12 C13 H13 120.6 . . ? C15 C14 C13 120.2(3) . . ? C15 C14 N2 120.6(3) . . ? C13 C14 N2 119.2(3) . . ? C14 C15 C16 119.2(4) . . ? C14 C15 H15 120.4 . . ? C16 C15 H15 120.4 . . ? C11 C16 C15 122.5(4) . . ? C11 C16 H16 118.7 . . ? C15 C16 H16 118.7 . . ? O2 C17 O1 126.4(3) . . ? O2 C17 C18 116.4(3) . . ? O1 C17 C18 117.2(3) . . ? O3 C18 C19 109.5(3) . . ? O3 C18 C17 109.5(2) . . ? C19 C18 C17 110.7(3) . . ? O3 C18 H18 109.0 . . ? C19 C18 H18 109.0 . . ? C17 C18 H18 109.0 . . ? O4 C19 C20 109.5(3) . . ? O4 C19 C18 109.5(3) . . ? C20 C19 C18 111.8(3) . . ? O4 C19 H19 108.7 . . ? C20 C19 H19 108.7 . . ? C18 C19 H19 108.7 . . ? O6 C20 O5 124.5(3) . . ? O6 C20 C19 121.5(3) . . ? O5 C20 C19 114.0(3) . . ? O7 C21 O8 126.4(3) . . ? O7 C21 C22 117.2(3) . . ? O8 C21 C22 116.4(3) . . ? O9 C22 C23 108.6(2) . . ? O9 C22 C21 110.2(2) . . ? C23 C22 C21 112.2(2) . . ? O9 C22 H22 108.6 . . ? C23 C22 H22 108.6 . . ? C21 C22 H22 108.6 . . ? O10 C23 C22 112.0(2) . . ? O10 C23 C24 113.8(2) . . ? C22 C23 C24 107.6(2) . . ? O10 C23 H23 107.7 . . ? C22 C23 H23 107.7 . . ? C24 C23 H23 107.7 . . ? O12 C24 O11 123.5(3) . . ? O12 C24 C23 121.3(3) . . ? O11 C24 C23 115.1(3) . . ? C6 N1 H1D 109.5 . . ? C6 N1 H1E 109.5 . . ? H1D N1 H1E 109.5 . . ? C6 N1 H1F 109.5 . . ? H1D N1 H1F 109.5 . . ? H1E N1 H1F 109.5 . . ? C14 N2 H2C 109.5 . . ? C14 N2 H2D 109.5 . . ? H2C N2 H2D 109.5 . . ? C14 N2 H2E 109.5 . . ? H2C N2 H2E 109.5 . . ? H2D N2 H2E 109.5 . . ? C18 O3 H3 109.5 . . ? C19 O4 H4A 109.5 . . ? C20 O5 H5A 109.5 . . ? C22 O9 H9 109.5 . . ? C23 O10 H10 109.5 . . ? C24 O11 H11 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 C1 C2 C3 C4 -180.0(5) . . . . ? C1 C2 C3 C8 -0.5(8) . . . . ? C8 C3 C4 C5 -0.2(7) . . . . ? C2 C3 C4 C5 179.3(4) . . . . ? C3 C4 C5 C6 -0.8(7) . . . . ? C4 C5 C6 C7 1.7(6) . . . . ? C4 C5 C6 N1 -179.7(4) . . . . ? C5 C6 C7 C8 -1.5(6) . . . . ? N1 C6 C7 C8 179.9(4) . . . . ? C4 C3 C8 C7 0.4(7) . . . . ? C2 C3 C8 C7 -179.1(5) . . . . ? C6 C7 C8 C3 0.4(7) . . . . ? C9 C10 C11 C12 176.7(5) . . . . ? C9 C10 C11 C16 -2.8(7) . . . . ? C16 C11 C12 C13 -0.3(6) . . . . ? C10 C11 C12 C13 -179.9(4) . . . . ? C11 C12 C13 C14 0.7(7) . . . . ? C12 C13 C14 C15 -0.9(6) . . . . ? C12 C13 C14 N2 179.6(3) . . . . ? C13 C14 C15 C16 0.7(5) . . . . ? N2 C14 C15 C16 -179.8(3) . . . . ? C12 C11 C16 C15 0.1(6) . . . . ? C10 C11 C16 C15 179.7(4) . . . . ? C14 C15 C16 C11 -0.3(6) . . . . ? O2 C17 C18 O3 -2.2(4) . . . . ? O1 C17 C18 O3 178.2(3) . . . . ? O2 C17 C18 C19 -123.1(3) . . . . ? O1 C17 C18 C19 57.3(4) . . . . ? O3 C18 C19 O4 -75.0(3) . . . . ? C17 C18 C19 O4 45.8(4) . . . . ? O3 C18 C19 C20 46.5(4) . . . . ? C17 C18 C19 C20 167.4(3) . . . . ? O4 C19 C20 O6 -5.0(5) . . . . ? C18 C19 C20 O6 -126.6(4) . . . . ? O4 C19 C20 O5 174.0(3) . . . . ? C18 C19 C20 O5 52.5(4) . . . . ? O7 C21 C22 O9 -3.5(4) . . . . ? O8 C21 C22 O9 177.6(3) . . . . ? O7 C21 C22 C23 -124.7(3) . . . . ? O8 C21 C22 C23 56.4(4) . . . . ? O9 C22 C23 O10 -66.4(3) . . . . ? C21 C22 C23 O10 55.7(3) . . . . ? O9 C22 C23 C24 59.4(3) . . . . ? C21 C22 C23 C24 -178.5(2) . . . . ? O10 C23 C24 O12 -162.2(3) . . . . ? C22 C23 C24 O12 73.1(4) . . . . ? O10 C23 C24 O11 21.3(4) . . . . ? C22 C23 C24 O11 -103.4(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 N1 H1D O7 0.89 1.85 2.723(3) 165.9 . N1 H1E O8 0.89 1.93 2.808(3) 170.8 1_655 N1 H1F O9 0.89 1.96 2.809(3) 158.5 1_565 N2 H2C O3 0.89 2.00 2.883(3) 169.4 1_556 N2 H2D O1 0.89 2.57 3.430(4) 162.9 1_646 N2 H2E O2 0.89 1.89 2.759(3) 166.8 1_546 O3 H3 O2 0.82 2.07 2.577(3) 119.7 . O4 H4A O6 0.82 2.15 2.639(4) 118.6 . O5 H5A O1 0.82 1.80 2.614(3) 169.1 1_545 O9 H9 O7 0.82 2.09 2.590(3) 118.7 . O9 H9 O12 0.82 2.19 2.784(3) 129.5 1_655 O10 H10 O1 0.82 2.08 2.772(3) 142.5 1_645 O11 H11 O8 0.82 1.74 2.554(3) 172.6 1_545 O10 H10 O9 0.82 2.52 2.897(3) 109.8 . C19 H19 O11 0.98 2.57 3.534(4) 169.5 1_465 _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 27.43 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.149 _refine_diff_density_min -0.189 _refine_diff_density_rms 0.039 #===END