Supplementary Material (ESI) for Organic & Biomolecular Chemistry This journal is (c) The Royal Society of Chemistry 2006 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author 'Jill Barber' _publ_contact_author_address ; School of Pharmacy and Pharmaceutical Sciences University of Manchester Manchester M13 9PL UNITED KINGDOM ; _publ_contact_letter ; ENTER TEXT OF LETTER ; _publ_requested_coeditor_name ? _publ_contact_author_email JILL.BARBER@MANCHESTER.AC.UK _publ_section_title ; Determination of the stereochemistry of anhydroerythromycin A, the principal degradation product of the antibiotic erythromycin A. ; _publ_section_abstract ; ENTER ABSTRACT ; loop_ _publ_author_name 'Jill Barber' 'Addolreza Hassanzadeh' 'Madeline Helliwell' _publ_contact_author_name 'Jill Barber' data_jb2bm _database_code_depnum_ccdc_archive 'CCDC 286533' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _publ_section_exptl_prep ; ENTER EXPERIMENTAL SECTION ; _publ_section_exptl_refinement ; The structure was solved by direct methods. All non-H atoms were refined anisotropically. H atoms were included in calculated positions. ; _publ_section_comment ; ENTER TEXT ; _publ_section_references ; ENTER OTHER REFERENCES ; _publ_section_acknowledgements ; ENTER ACKNOWLEDGEMENTS ; _publ_section_table_legends ; ENTER TABLE LEGENDS ; _publ_section_figure_captions ; ENTER FIGURE CAPTIONS ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C39 H68 N O13.50' _chemical_formula_weight 766.94 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' _cell_length_a 28.764(3) _cell_length_b 12.3834(13) _cell_length_c 11.8736(13) _cell_angle_alpha 90.00 _cell_angle_beta 104.728(2) _cell_angle_gamma 90.00 _cell_volume 4090.4(8) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 8289 _cell_measurement_theta_min 2.39 _cell_measurement_theta_max 26.44 _exptl_crystal_description irregular _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.245 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1668 _exptl_absorpt_coefficient_mu 0.093 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16413 _diffrn_reflns_av_R_equivalents 0.0464 _diffrn_reflns_av_sigmaI/netI 0.0356 _diffrn_reflns_limit_h_min -36 _diffrn_reflns_limit_h_max 36 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.77 _diffrn_reflns_theta_max 26.46 _reflns_number_total 4428 _reflns_number_gt 4096 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SIR-97 (Altomare, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker 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^)+(0.0386P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _chemical_absolute_configuration syn _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.2(6) _refine_ls_number_reflns 4428 _refine_ls_number_parameters 503 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0343 _refine_ls_R_factor_gt 0.0314 _refine_ls_wR_factor_ref 0.0731 _refine_ls_wR_factor_gt 0.0722 _refine_ls_goodness_of_fit_ref 1.137 _refine_ls_restrained_S_all 1.136 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.71989(4) 0.39247(11) 0.23221(11) 0.0163(3) Uani 1 1 d . . . O2 O 0.64836(4) 0.44158(11) 0.10520(11) 0.0165(3) Uani 1 1 d . . . O3 O 0.59611(5) 0.17613(12) 0.06413(13) 0.0239(3) Uani 1 1 d . . . H3 H 0.5678 0.1790 0.0280 0.036 Uiso 1 1 calc R . . O4 O 0.63532(5) 0.30840(11) 0.29767(11) 0.0158(3) Uani 1 1 d . . . O5 O 0.65743(5) 0.45526(12) 0.41188(12) 0.0217(3) Uani 1 1 d . . . O6 O 0.78347(5) 0.32814(11) 0.58360(11) 0.0166(3) Uani 1 1 d . . . O7 O 0.81873(5) 0.50006(11) 0.60529(12) 0.0182(3) Uani 1 1 d . . . O8 O 0.93825(5) 0.45256(12) 0.80439(12) 0.0196(3) Uani 1 1 d . . . H8 H 0.9461 0.3985 0.7737 0.029 Uiso 1 1 calc R . . O9 O 0.87430(5) 0.27922(11) 0.76551(12) 0.0187(3) Uani 1 1 d . . . O10 O 0.83920(4) 0.29898(11) 0.28297(11) 0.0162(3) Uani 1 1 d . . . O11 O 0.88020(5) 0.45077(11) 0.25996(12) 0.0185(3) Uani 1 1 d . . . O12 O 0.92575(5) 0.18012(11) 0.34533(12) 0.0185(3) Uani 1 1 d . . . O13 O 0.88950(7) 0.07944(14) 0.18956(15) 0.0403(4) Uani 1 1 d . . . N1 N 1.00898(6) 0.27769(15) 0.26737(14) 0.0178(4) Uani 1 1 d . . . C1 C 0.76890(7) 0.42438(16) 0.23600(16) 0.0162(4) Uani 1 1 d . . . C2 C 0.77214(7) 0.40835(17) 0.11019(16) 0.0178(4) Uani 1 1 d . . . H2A H 0.7950 0.4579 0.0906 0.021 Uiso 1 1 calc R . . H2B H 0.7812 0.3349 0.0969 0.021 Uiso 1 1 calc R . . C3 C 0.72073(7) 0.43336(17) 0.04108(16) 0.0173(4) Uani 1 1 d . . . H3A H 0.7165 0.5113 0.0486 0.021 Uiso 1 1 calc R . . C4 C 0.69090(7) 0.37928(16) 0.11559(16) 0.0158(4) Uani 1 1 d . . . C5 C 0.67374(7) 0.26046(16) 0.09726(17) 0.0173(4) Uani 1 1 d . . . H5 H 0.6771 0.2303 0.1753 0.021 Uiso 1 1 calc R . . C6 C 0.61991(7) 0.27130(17) 0.04332(17) 0.0181(4) Uani 1 1 d . . . H6 H 0.6144 0.2814 -0.0409 0.022 Uiso 1 1 calc R . . C7 C 0.60647(7) 0.37590(17) 0.09703(16) 0.0171(4) Uani 1 1 d . . . C8 C 0.77499(7) 0.54284(16) 0.27241(18) 0.0190(4) Uani 1 1 d . . . H8A H 0.7539 0.5866 0.2146 0.029 Uiso 1 1 calc R . . H8B H 0.8077 0.5645 0.2796 0.029 Uiso 1 1 calc R . . H8C H 0.7673 0.5519 0.3459 0.029 Uiso 1 1 calc R . . C9 C 0.70752(7) 0.40975(19) -0.08935(17) 0.0237(5) Uani 1 1 d . . . H9A H 0.7205 0.4651 -0.1290 0.036 Uiso 1 1 calc R . . H9B H 0.6732 0.4083 -0.1181 0.036 Uiso 1 1 calc R . . H9C H 0.7205 0.3410 -0.1029 0.036 Uiso 1 1 calc R . . C10 C 0.69867(8) 0.18104(18) 0.03346(18) 0.0236(5) Uani 1 1 d . . . H10A H 0.6858 0.1100 0.0369 0.035 Uiso 1 1 calc R . . H10B H 0.7325 0.1805 0.0697 0.035 Uiso 1 1 calc R . . H10C H 0.6934 0.2028 -0.0464 0.035 Uiso 1 1 calc R . . C11 C 0.56496(7) 0.43503(19) 0.01434(17) 0.0222(5) Uani 1 1 d . . . H11A H 0.5553 0.4953 0.0540 0.033 Uiso 1 1 calc R . . H11B H 0.5383 0.3865 -0.0110 0.033 Uiso 1 1 calc R . . H11C H 0.5751 0.4605 -0.0520 0.033 Uiso 1 1 calc R . . C12 C 0.59663(7) 0.36838(18) 0.21887(16) 0.0176(4) Uani 1 1 d . . . H12 H 0.5969 0.4420 0.2493 0.021 Uiso 1 1 calc R . . C13 C 0.54959(7) 0.3144(2) 0.22721(18) 0.0259(5) Uani 1 1 d . . . H13A H 0.5232 0.3426 0.1664 0.031 Uiso 1 1 calc R . . H13B H 0.5516 0.2373 0.2150 0.031 Uiso 1 1 calc R . . C14 C 0.53950(8) 0.3346(2) 0.3456(2) 0.0301(5) Uani 1 1 d . . . H14A H 0.5647 0.3032 0.4057 0.045 Uiso 1 1 calc R . . H14B H 0.5093 0.3023 0.3471 0.045 Uiso 1 1 calc R . . H14C H 0.5381 0.4109 0.3586 0.045 Uiso 1 1 calc R . . C15 C 0.66322(7) 0.36224(17) 0.38975(16) 0.0152(4) Uani 1 1 d . . . C16 C 0.70068(6) 0.28947(16) 0.46658(16) 0.0144(4) Uani 1 1 d . . . H16 H 0.6971 0.2159 0.4350 0.017 Uiso 1 1 calc R . . C17 C 0.68996(7) 0.28988(17) 0.58710(16) 0.0184(4) Uani 1 1 d . . . H17A H 0.6912 0.3626 0.6156 0.028 Uiso 1 1 calc R . . H17B H 0.7135 0.2468 0.6401 0.028 Uiso 1 1 calc R . . H17C H 0.6585 0.2605 0.5807 0.028 Uiso 1 1 calc R . . C18 C 0.75189(7) 0.33280(16) 0.46817(15) 0.0146(4) Uani 1 1 d . . . H18 H 0.7488 0.4085 0.4432 0.017 Uiso 1 1 calc R . . C19 C 0.78874(7) 0.42650(16) 0.64567(16) 0.0172(4) Uani 1 1 d . . . H19 H 0.7568 0.4594 0.6331 0.021 Uiso 1 1 calc R . . C20 C 0.80693(7) 0.40172(18) 0.77445(17) 0.0193(4) Uani 1 1 d . . . H20A H 0.7892 0.3404 0.7927 0.023 Uiso 1 1 calc R . . H20B H 0.8000 0.4630 0.8183 0.023 Uiso 1 1 calc R . . C21 C 0.86086(7) 0.37671(18) 0.81527(16) 0.0185(4) Uani 1 1 d . . . C22 C 0.88733(7) 0.46545(17) 0.76795(17) 0.0172(4) Uani 1 1 d . . . H22 H 0.8795 0.5342 0.7997 0.021 Uiso 1 1 calc R . . C23 C 0.86915(7) 0.47176(16) 0.63532(17) 0.0164(4) Uani 1 1 d . . . H23 H 0.8734 0.4016 0.6011 0.020 Uiso 1 1 calc R . . C24 C 0.87637(8) 0.3722(2) 0.94811(17) 0.0250(5) Uani 1 1 d . . . H24A H 0.8569 0.3205 0.9756 0.038 Uiso 1 1 calc R . . H24B H 0.8724 0.4421 0.9793 0.038 Uiso 1 1 calc R . . H24C H 0.9095 0.3512 0.9729 0.038 Uiso 1 1 calc R . . C25 C 0.85307(9) 0.18140(19) 0.7910(2) 0.0299(5) Uani 1 1 d . . . H25A H 0.8615 0.1699 0.8737 0.045 Uiso 1 1 calc R . . H25B H 0.8646 0.1222 0.7535 0.045 Uiso 1 1 calc R . . H25C H 0.8188 0.1862 0.7630 0.045 Uiso 1 1 calc R . . C26 C 0.89375(8) 0.55859(17) 0.58204(18) 0.0223(5) Uani 1 1 d . . . H26A H 0.8789 0.5633 0.5001 0.034 Uiso 1 1 calc R . . H26B H 0.9271 0.5409 0.5940 0.034 Uiso 1 1 calc R . . H26C H 0.8908 0.6267 0.6182 0.034 Uiso 1 1 calc R . . C27 C 0.77642(7) 0.26967(16) 0.38622(17) 0.0154(4) Uani 1 1 d . . . H27 H 0.7511 0.2375 0.3240 0.018 Uiso 1 1 calc R . . C28 C 0.80839(7) 0.17842(17) 0.44933(18) 0.0204(4) Uani 1 1 d . . . H28A H 0.8185 0.1342 0.3935 0.031 Uiso 1 1 calc R . . H28B H 0.7907 0.1352 0.4911 0.031 Uiso 1 1 calc R . . H28C H 0.8361 0.2085 0.5030 0.031 Uiso 1 1 calc R . . C29 C 0.80351(7) 0.35228(16) 0.33067(16) 0.0149(4) Uani 1 1 d . . . H29 H 0.8207 0.4005 0.3928 0.018 Uiso 1 1 calc R . . C30 C 0.88392(7) 0.34820(16) 0.31455(17) 0.0161(4) Uani 1 1 d . . . H30 H 0.8937 0.3574 0.3993 0.019 Uiso 1 1 calc R . . C31 C 0.92059(7) 0.27790(16) 0.27614(17) 0.0157(4) Uani 1 1 d . . . H31 H 0.9094 0.2607 0.1931 0.019 Uiso 1 1 calc R . . C32 C 0.96976(7) 0.33511(16) 0.30188(16) 0.0160(4) Uani 1 1 d . . . H32 H 0.9802 0.3444 0.3865 0.019 Uiso 1 1 calc R . . C33 C 0.96262(7) 0.44831(17) 0.24952(17) 0.0177(4) Uani 1 1 d . . . H33A H 0.9928 0.4876 0.2716 0.021 Uiso 1 1 calc R . . H33B H 0.9532 0.4430 0.1653 0.021 Uiso 1 1 calc R . . C34 C 0.92452(7) 0.50971(17) 0.29082(18) 0.0189(4) Uani 1 1 d . . . H34 H 0.9348 0.5172 0.3757 0.023 Uiso 1 1 calc R . . C35 C 0.90733(8) 0.08728(18) 0.2923(2) 0.0256(5) Uani 1 1 d . . . C36 C 0.91336(9) -0.0024(2) 0.3798(2) 0.0363(6) Uani 1 1 d . . . H36A H 0.9034 -0.0693 0.3403 0.054 Uiso 1 1 calc R . . H36B H 0.8940 0.0122 0.4331 0.054 Uiso 1 1 calc R . . H36C H 0.9465 -0.0073 0.4220 0.054 Uiso 1 1 calc R . . C37 C 1.03439(8) 0.19818(19) 0.35147(19) 0.0264(5) Uani 1 1 d . . . H37A H 1.0146 0.1352 0.3484 0.040 Uiso 1 1 calc R . . H37B H 1.0414 0.2286 0.4283 0.040 Uiso 1 1 calc R . . H37C H 1.0639 0.1784 0.3330 0.040 Uiso 1 1 calc R . . C38 C 0.99579(8) 0.23087(19) 0.15023(17) 0.0238(5) Uani 1 1 d . . . H38A H 1.0242 0.2059 0.1300 0.036 Uiso 1 1 calc R . . H38B H 0.9802 0.2847 0.0953 0.036 Uiso 1 1 calc R . . H38C H 0.9743 0.1713 0.1486 0.036 Uiso 1 1 calc R . . C39 C 0.91429(8) 0.62047(18) 0.2365(2) 0.0269(5) Uani 1 1 d . . . H39A H 0.9017 0.6133 0.1539 0.040 Uiso 1 1 calc R . . H39B H 0.9435 0.6617 0.2523 0.040 Uiso 1 1 calc R . . H39C H 0.8912 0.6568 0.2690 0.040 Uiso 1 1 calc R . . O1S O 0.0000 0.58002(18) 0.0000 0.0238(5) Uani 1 2 d S . . H1S H 0.0153(10) 0.539(2) 0.053(2) 0.046(9) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0103(6) 0.0230(8) 0.0152(7) -0.0011(6) 0.0028(5) -0.0022(6) O2 0.0115(6) 0.0158(7) 0.0219(7) 0.0005(6) 0.0040(5) -0.0004(6) O3 0.0206(8) 0.0219(8) 0.0257(8) 0.0033(7) -0.0007(6) -0.0070(6) O4 0.0128(7) 0.0183(7) 0.0148(7) 0.0013(6) 0.0007(5) -0.0015(5) O5 0.0215(8) 0.0192(8) 0.0223(8) -0.0015(6) 0.0018(6) 0.0032(6) O6 0.0145(7) 0.0169(7) 0.0163(7) -0.0020(5) 0.0002(5) 0.0005(5) O7 0.0132(7) 0.0185(7) 0.0215(7) -0.0009(6) 0.0018(6) 0.0001(6) O8 0.0128(7) 0.0222(8) 0.0225(7) -0.0070(6) 0.0018(5) 0.0010(6) O9 0.0177(7) 0.0170(7) 0.0223(7) -0.0003(6) 0.0067(5) -0.0005(6) O10 0.0104(6) 0.0189(7) 0.0194(7) -0.0016(6) 0.0042(5) -0.0005(5) O11 0.0128(7) 0.0181(7) 0.0242(7) 0.0038(6) 0.0041(5) -0.0003(6) O12 0.0171(7) 0.0178(7) 0.0203(7) 0.0026(6) 0.0043(6) 0.0010(6) O13 0.0560(12) 0.0334(10) 0.0331(10) -0.0145(8) 0.0141(8) -0.0171(9) N1 0.0129(8) 0.0242(9) 0.0163(8) 0.0015(7) 0.0037(6) 0.0025(7) C1 0.0108(9) 0.0189(10) 0.0191(10) -0.0006(8) 0.0042(7) -0.0018(8) C2 0.0139(9) 0.0215(10) 0.0185(10) 0.0015(8) 0.0050(8) 0.0008(8) C3 0.0152(9) 0.0186(10) 0.0183(10) 0.0013(8) 0.0047(7) 0.0003(8) C4 0.0115(9) 0.0177(10) 0.0166(9) 0.0008(8) 0.0007(7) 0.0027(8) C5 0.0161(10) 0.0176(10) 0.0169(10) 0.0012(8) 0.0022(7) 0.0004(8) C6 0.0183(10) 0.0189(10) 0.0157(9) 0.0012(8) 0.0017(7) -0.0041(8) C7 0.0122(9) 0.0220(11) 0.0161(9) 0.0017(8) 0.0014(7) -0.0028(8) C8 0.0163(10) 0.0182(11) 0.0219(11) 0.0022(8) 0.0038(8) 0.0018(8) C9 0.0186(10) 0.0318(12) 0.0207(10) 0.0030(9) 0.0052(8) -0.0002(9) C10 0.0269(11) 0.0191(11) 0.0249(11) -0.0023(9) 0.0069(9) 0.0018(9) C11 0.0146(10) 0.0300(12) 0.0207(10) 0.0060(9) 0.0023(8) 0.0016(9) C12 0.0120(9) 0.0232(10) 0.0163(9) 0.0019(8) 0.0013(7) 0.0011(8) C13 0.0144(10) 0.0420(14) 0.0192(10) 0.0050(10) 0.0004(8) -0.0033(9) C14 0.0209(11) 0.0398(14) 0.0325(13) 0.0019(11) 0.0122(10) -0.0009(10) C15 0.0126(9) 0.0188(10) 0.0156(9) -0.0002(8) 0.0060(7) -0.0028(8) C16 0.0141(9) 0.0143(9) 0.0145(9) -0.0015(8) 0.0034(7) -0.0002(8) C17 0.0154(10) 0.0224(11) 0.0173(10) 0.0020(9) 0.0041(8) -0.0037(8) C18 0.0131(9) 0.0141(9) 0.0156(10) 0.0007(8) 0.0019(7) 0.0003(7) C19 0.0120(9) 0.0203(11) 0.0186(10) -0.0037(8) 0.0026(7) 0.0010(8) C20 0.0145(10) 0.0258(11) 0.0181(10) -0.0045(8) 0.0050(8) -0.0004(8) C21 0.0154(10) 0.0248(11) 0.0148(9) -0.0035(8) 0.0033(7) 0.0007(8) C22 0.0118(10) 0.0183(10) 0.0202(10) -0.0071(8) 0.0013(8) 0.0004(8) C23 0.0131(10) 0.0164(10) 0.0192(10) -0.0042(8) 0.0031(8) 0.0009(8) C24 0.0198(11) 0.0371(13) 0.0165(10) -0.0023(10) 0.0014(8) 0.0018(10) C25 0.0311(13) 0.0240(12) 0.0369(13) 0.0027(10) 0.0129(10) -0.0032(10) C26 0.0201(11) 0.0209(11) 0.0257(11) -0.0010(9) 0.0053(9) -0.0002(9) C27 0.0125(9) 0.0155(10) 0.0173(9) -0.0018(8) 0.0024(7) -0.0015(8) C28 0.0196(10) 0.0195(11) 0.0238(11) 0.0007(9) 0.0089(8) 0.0020(9) C29 0.0133(9) 0.0158(10) 0.0152(9) -0.0051(8) 0.0031(7) -0.0013(8) C30 0.0121(9) 0.0190(10) 0.0163(10) 0.0002(8) 0.0017(7) -0.0013(8) C31 0.0154(9) 0.0178(10) 0.0137(9) 0.0029(8) 0.0033(7) 0.0007(8) C32 0.0121(9) 0.0225(11) 0.0132(9) 0.0006(8) 0.0026(7) 0.0000(8) C33 0.0147(9) 0.0209(10) 0.0175(10) 0.0005(8) 0.0040(7) -0.0031(8) C34 0.0156(10) 0.0206(10) 0.0201(10) -0.0018(8) 0.0038(8) -0.0024(8) C35 0.0241(12) 0.0214(11) 0.0353(13) -0.0029(10) 0.0150(10) -0.0016(9) C36 0.0367(14) 0.0225(12) 0.0544(16) 0.0038(11) 0.0202(12) -0.0009(11) C37 0.0211(11) 0.0324(13) 0.0270(11) 0.0084(10) 0.0086(9) 0.0072(10) C38 0.0183(11) 0.0328(12) 0.0218(11) -0.0039(9) 0.0077(8) 0.0020(9) C39 0.0214(11) 0.0211(11) 0.0404(14) 0.0015(10) 0.0122(10) -0.0008(9) O1S 0.0222(12) 0.0222(12) 0.0238(12) 0.000 0.0000(9) 0.000 _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C4 1.433(2) . ? O1 C1 1.454(2) . ? O2 C4 1.425(2) . ? O2 C7 1.436(2) . ? O3 C6 1.416(2) . ? O3 H3 0.8200 . ? O4 C15 1.356(2) . ? O4 C12 1.461(2) . ? O5 C15 1.203(2) . ? O6 C19 1.412(2) . ? O6 C18 1.440(2) . ? O7 C19 1.419(2) . ? O7 C23 1.446(2) . ? O8 C22 1.427(2) . ? O8 H8 0.8200 . ? O9 C25 1.423(3) . ? O9 C21 1.439(2) . ? O10 C30 1.386(2) . ? O10 C29 1.451(2) . ? O11 C30 1.418(2) . ? O11 C34 1.433(2) . ? O12 C35 1.352(3) . ? O12 C31 1.450(2) . ? O13 C35 1.201(3) . ? N1 C37 1.459(3) . ? N1 C38 1.465(3) . ? N1 C32 1.477(2) . ? C1 C8 1.527(3) . ? C1 C2 1.533(3) . ? C1 C29 1.576(3) . ? C2 C3 1.529(3) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C9 1.526(3) . ? C3 C4 1.534(3) . ? C3 H3A 0.9800 . ? C4 C5 1.550(3) . ? C5 C6 1.523(3) . ? C5 C10 1.527(3) . ? C5 H5 0.9800 . ? C6 C7 1.536(3) . ? C6 H6 0.9800 . ? C7 C11 1.526(3) . ? C7 C12 1.546(3) . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 C13 1.535(3) . ? C12 H12 0.9800 . ? C13 C14 1.527(3) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 C16 1.518(3) . ? C16 C17 1.539(3) . ? C16 C18 1.563(3) . ? C16 H16 0.9800 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 C27 1.551(3) . ? C18 H18 0.9800 . ? C19 C20 1.516(3) . ? C19 H19 0.9800 . ? C20 C21 1.534(3) . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C21 C22 1.523(3) . ? C21 C24 1.527(3) . ? C22 C23 1.530(3) . ? C22 H22 0.9800 . ? C23 C26 1.511(3) . ? C23 H23 0.9800 . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? C25 H25A 0.9600 . ? C25 H25B 0.9600 . ? C25 H25C 0.9600 . ? C26 H26A 0.9600 . ? C26 H26B 0.9600 . ? C26 H26C 0.9600 . ? C27 C28 1.528(3) . ? C27 C29 1.533(3) . ? C27 H27 0.9800 . ? C28 H28A 0.9600 . ? C28 H28B 0.9600 . ? C28 H28C 0.9600 . ? C29 H29 0.9800 . ? C30 C31 1.524(3) . ? C30 H30 0.9800 . ? C31 C32 1.541(3) . ? C31 H31 0.9800 . ? C32 C33 1.526(3) . ? C32 H32 0.9800 . ? C33 C34 1.514(3) . ? C33 H33A 0.9700 . ? C33 H33B 0.9700 . ? C34 C39 1.512(3) . ? C34 H34 0.9800 . ? C35 C36 1.500(3) . ? C36 H36A 0.9600 . ? C36 H36B 0.9600 . ? C36 H36C 0.9600 . ? C37 H37A 0.9600 . ? C37 H37B 0.9600 . ? C37 H37C 0.9600 . ? C38 H38A 0.9600 . ? C38 H38B 0.9600 . ? C38 H38C 0.9600 . ? C39 H39A 0.9600 . ? C39 H39B 0.9600 . ? C39 H39C 0.9600 . ? O1S H1S 0.84(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C4 O1 C1 112.49(13) . . ? C4 O2 C7 112.72(15) . . ? C6 O3 H3 109.5 . . ? C15 O4 C12 117.69(15) . . ? C19 O6 C18 114.86(14) . . ? C19 O7 C23 114.76(14) . . ? C22 O8 H8 109.5 . . ? C25 O9 C21 116.86(15) . . ? C30 O10 C29 113.23(14) . . ? C30 O11 C34 112.36(14) . . ? C35 O12 C31 118.35(15) . . ? C37 N1 C38 110.26(18) . . ? C37 N1 C32 114.83(15) . . ? C38 N1 C32 114.99(15) . . ? O1 C1 C8 108.09(15) . . ? O1 C1 C2 103.50(14) . . ? C8 C1 C2 111.67(17) . . ? O1 C1 C29 107.45(15) . . ? C8 C1 C29 109.65(15) . . ? C2 C1 C29 115.96(16) . . ? C3 C2 C1 101.91(15) . . ? C3 C2 H2A 111.4 . . ? C1 C2 H2A 111.4 . . ? C3 C2 H2B 111.4 . . ? C1 C2 H2B 111.4 . . ? H2A C2 H2B 109.3 . . ? C9 C3 C2 117.58(16) . . ? C9 C3 C4 118.04(17) . . ? C2 C3 C4 102.03(15) . . ? C9 C3 H3A 106.1 . . ? C2 C3 H3A 106.1 . . ? C4 C3 H3A 106.1 . . ? O2 C4 O1 107.33(14) . . ? O2 C4 C3 107.91(15) . . ? O1 C4 C3 103.55(14) . . ? O2 C4 C5 105.43(15) . . ? O1 C4 C5 109.29(15) . . ? C3 C4 C5 122.58(17) . . ? C6 C5 C10 113.80(17) . . ? C6 C5 C4 103.22(15) . . ? C10 C5 C4 120.54(17) . . ? C6 C5 H5 106.1 . . ? C10 C5 H5 106.1 . . ? C4 C5 H5 106.1 . . ? O3 C6 C5 109.76(16) . . ? O3 C6 C7 116.46(16) . . ? C5 C6 C7 103.65(15) . . ? O3 C6 H6 108.9 . . ? C5 C6 H6 108.9 . . ? C7 C6 H6 108.9 . . ? O2 C7 C11 106.10(16) . . ? O2 C7 C6 102.13(15) . . ? C11 C7 C6 112.07(16) . . ? O2 C7 C12 108.72(15) . . ? C11 C7 C12 109.36(16) . . ? C6 C7 C12 117.58(17) . . ? C1 C8 H8A 109.5 . . ? C1 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C1 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C3 C9 H9A 109.5 . . ? C3 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C3 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C5 C10 H10A 109.5 . . ? C5 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C5 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C7 C11 H11A 109.5 . . ? C7 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C7 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? O4 C12 C13 106.13(16) . . ? O4 C12 C7 109.81(15) . . ? C13 C12 C7 117.44(16) . . ? O4 C12 H12 107.7 . . ? C13 C12 H12 107.7 . . ? C7 C12 H12 107.7 . . ? C14 C13 C12 111.44(18) . . ? C14 C13 H13A 109.3 . . ? C12 C13 H13A 109.3 . . ? C14 C13 H13B 109.3 . . ? C12 C13 H13B 109.3 . . ? H13A C13 H13B 108.0 . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? O5 C15 O4 124.11(18) . . ? O5 C15 C16 123.63(17) . . ? O4 C15 C16 112.14(16) . . ? C15 C16 C17 106.10(15) . . ? C15 C16 C18 109.04(15) . . ? C17 C16 C18 113.50(15) . . ? C15 C16 H16 109.4 . . ? C17 C16 H16 109.4 . . ? C18 C16 H16 109.4 . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? O6 C18 C27 107.43(15) . . ? O6 C18 C16 111.23(14) . . ? C27 C18 C16 113.40(15) . . ? O6 C18 H18 108.2 . . ? C27 C18 H18 108.2 . . ? C16 C18 H18 108.2 . . ? O6 C19 O7 111.80(15) . . ? O6 C19 C20 108.39(16) . . ? O7 C19 C20 112.77(15) . . ? O6 C19 H19 107.9 . . ? O7 C19 H19 107.9 . . ? C20 C19 H19 107.9 . . ? C19 C20 C21 114.92(16) . . ? C19 C20 H20A 108.5 . . ? C21 C20 H20A 108.5 . . ? C19 C20 H20B 108.5 . . ? C21 C20 H20B 108.5 . . ? H20A C20 H20B 107.5 . . ? O9 C21 C22 104.01(15) . . ? O9 C21 C24 110.79(17) . . ? C22 C21 C24 111.41(17) . . ? O9 C21 C20 113.27(16) . . ? C22 C21 C20 107.32(17) . . ? C24 C21 C20 109.88(16) . . ? O8 C22 C21 112.22(16) . . ? O8 C22 C23 111.94(15) . . ? C21 C22 C23 110.15(15) . . ? O8 C22 H22 107.4 . . ? C21 C22 H22 107.4 . . ? C23 C22 H22 107.4 . . ? O7 C23 C26 105.74(16) . . ? O7 C23 C22 108.97(15) . . ? C26 C23 C22 113.17(16) . . ? O7 C23 H23 109.6 . . ? C26 C23 H23 109.6 . . ? C22 C23 H23 109.6 . . ? C21 C24 H24A 109.5 . . ? C21 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C21 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? O9 C25 H25A 109.5 . . ? O9 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? O9 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C23 C26 H26A 109.5 . . ? C23 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C23 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C28 C27 C29 113.36(16) . . ? C28 C27 C18 112.22(16) . . ? C29 C27 C18 107.20(15) . . ? C28 C27 H27 108.0 . . ? C29 C27 H27 108.0 . . ? C18 C27 H27 108.0 . . ? C27 C28 H28A 109.5 . . ? C27 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C27 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? O10 C29 C27 110.60(15) . . ? O10 C29 C1 111.14(14) . . ? C27 C29 C1 112.77(15) . . ? O10 C29 H29 107.3 . . ? C27 C29 H29 107.3 . . ? C1 C29 H29 107.3 . . ? O10 C30 O11 108.26(15) . . ? O10 C30 C31 109.45(16) . . ? O11 C30 C31 110.64(15) . . ? O10 C30 H30 109.5 . . ? O11 C30 H30 109.5 . . ? C31 C30 H30 109.5 . . ? O12 C31 C30 106.65(14) . . ? O12 C31 C32 108.35(15) . . ? C30 C31 C32 110.37(16) . . ? O12 C31 H31 110.5 . . ? C30 C31 H31 110.5 . . ? C32 C31 H31 110.5 . . ? N1 C32 C33 111.24(15) . . ? N1 C32 C31 116.79(17) . . ? C33 C32 C31 108.65(15) . . ? N1 C32 H32 106.5 . . ? C33 C32 H32 106.5 . . ? C31 C32 H32 106.5 . . ? C34 C33 C32 111.27(16) . . ? C34 C33 H33A 109.4 . . ? C32 C33 H33A 109.4 . . ? C34 C33 H33B 109.4 . . ? C32 C33 H33B 109.4 . . ? H33A C33 H33B 108.0 . . ? O11 C34 C33 109.36(16) . . ? O11 C34 C39 106.78(16) . . ? C33 C34 C39 113.32(17) . . ? O11 C34 H34 109.1 . . ? C33 C34 H34 109.1 . . ? C39 C34 H34 109.1 . . ? O13 C35 O12 123.8(2) . . ? O13 C35 C36 126.0(2) . . ? O12 C35 C36 110.14(19) . . ? C35 C36 H36A 109.5 . . ? C35 C36 H36B 109.5 . . ? H36A C36 H36B 109.5 . . ? C35 C36 H36C 109.5 . . ? H36A C36 H36C 109.5 . . ? H36B C36 H36C 109.5 . . ? N1 C37 H37A 109.5 . . ? N1 C37 H37B 109.5 . . ? H37A C37 H37B 109.5 . . ? N1 C37 H37C 109.5 . . ? H37A C37 H37C 109.5 . . ? H37B C37 H37C 109.5 . . ? N1 C38 H38A 109.5 . . ? N1 C38 H38B 109.5 . . ? H38A C38 H38B 109.5 . . ? N1 C38 H38C 109.5 . . ? H38A C38 H38C 109.5 . . ? H38B C38 H38C 109.5 . . ? C34 C39 H39A 109.5 . . ? C34 C39 H39B 109.5 . . ? H39A C39 H39B 109.5 . . ? C34 C39 H39C 109.5 . . ? H39A C39 H39C 109.5 . . ? H39B C39 H39C 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 C4 O1 C1 C8 107.30(17) . . . . ? C4 O1 C1 C2 -11.2(2) . . . . ? C4 O1 C1 C29 -134.44(15) . . . . ? O1 C1 C2 C3 31.92(19) . . . . ? C8 C1 C2 C3 -84.12(19) . . . . ? C29 C1 C2 C3 149.31(16) . . . . ? C1 C2 C3 C9 -171.10(18) . . . . ? C1 C2 C3 C4 -40.29(19) . . . . ? C7 O2 C4 O1 -109.01(16) . . . . ? C7 O2 C4 C3 139.97(15) . . . . ? C7 O2 C4 C5 7.4(2) . . . . ? C1 O1 C4 O2 -128.26(16) . . . . ? C1 O1 C4 C3 -14.3(2) . . . . ? C1 O1 C4 C5 117.88(16) . . . . ? C9 C3 C4 O2 -82.1(2) . . . . ? C2 C3 C4 O2 147.37(15) . . . . ? C9 C3 C4 O1 164.34(17) . . . . ? C2 C3 C4 O1 33.80(18) . . . . ? C9 C3 C4 C5 40.5(3) . . . . ? C2 C3 C4 C5 -90.1(2) . . . . ? O2 C4 C5 C6 15.70(19) . . . . ? O1 C4 C5 C6 130.79(15) . . . . ? C3 C4 C5 C6 -108.00(19) . . . . ? O2 C4 C5 C10 144.01(17) . . . . ? O1 C4 C5 C10 -100.9(2) . . . . ? C3 C4 C5 C10 20.3(3) . . . . ? C10 C5 C6 O3 71.2(2) . . . . ? C4 C5 C6 O3 -156.38(16) . . . . ? C10 C5 C6 C7 -163.71(17) . . . . ? C4 C5 C6 C7 -31.32(19) . . . . ? C4 O2 C7 C11 -144.59(16) . . . . ? C4 O2 C7 C6 -27.07(19) . . . . ? C4 O2 C7 C12 97.88(18) . . . . ? O3 C6 C7 O2 156.13(15) . . . . ? C5 C6 C7 O2 35.51(18) . . . . ? O3 C6 C7 C11 -90.7(2) . . . . ? C5 C6 C7 C11 148.67(16) . . . . ? O3 C6 C7 C12 37.3(2) . . . . ? C5 C6 C7 C12 -83.36(19) . . . . ? C15 O4 C12 C13 -116.83(18) . . . . ? C15 O4 C12 C7 115.29(17) . . . . ? O2 C7 C12 O4 -66.6(2) . . . . ? C11 C7 C12 O4 177.92(16) . . . . ? C6 C7 C12 O4 48.7(2) . . . . ? O2 C7 C12 C13 172.04(18) . . . . ? C11 C7 C12 C13 56.6(2) . . . . ? C6 C7 C12 C13 -72.7(2) . . . . ? O4 C12 C13 C14 69.3(2) . . . . ? C7 C12 C13 C14 -167.49(19) . . . . ? C12 O4 C15 O5 1.7(3) . . . . ? C12 O4 C15 C16 177.92(14) . . . . ? O5 C15 C16 C17 57.3(2) . . . . ? O4 C15 C16 C17 -118.86(16) . . . . ? O5 C15 C16 C18 -65.2(2) . . . . ? O4 C15 C16 C18 118.55(16) . . . . ? C19 O6 C18 C27 136.79(15) . . . . ? C19 O6 C18 C16 -98.57(18) . . . . ? C15 C16 C18 O6 138.21(16) . . . . ? C17 C16 C18 O6 20.2(2) . . . . ? C15 C16 C18 C27 -100.58(18) . . . . ? C17 C16 C18 C27 141.39(17) . . . . ? C18 O6 C19 O7 -75.36(19) . . . . ? C18 O6 C19 C20 159.73(14) . . . . ? C23 O7 C19 O6 -71.46(19) . . . . ? C23 O7 C19 C20 51.0(2) . . . . ? O6 C19 C20 C21 78.2(2) . . . . ? O7 C19 C20 C21 -46.2(2) . . . . ? C25 O9 C21 C22 -177.48(17) . . . . ? C25 O9 C21 C24 62.7(2) . . . . ? C25 O9 C21 C20 -61.3(2) . . . . ? C19 C20 C21 O9 -65.1(2) . . . . ? C19 C20 C21 C22 49.1(2) . . . . ? C19 C20 C21 C24 170.40(18) . . . . ? O9 C21 C22 O8 -61.90(18) . . . . ? C24 C21 C22 O8 57.5(2) . . . . ? C20 C21 C22 O8 177.81(15) . . . . ? O9 C21 C22 C23 63.54(18) . . . . ? C24 C21 C22 C23 -177.07(16) . . . . ? C20 C21 C22 C23 -56.7(2) . . . . ? C19 O7 C23 C26 178.78(15) . . . . ? C19 O7 C23 C22 -59.28(19) . . . . ? O8 C22 C23 O7 -171.92(15) . . . . ? C21 C22 C23 O7 62.5(2) . . . . ? O8 C22 C23 C26 -54.6(2) . . . . ? C21 C22 C23 C26 179.80(17) . . . . ? O6 C18 C27 C28 30.0(2) . . . . ? C16 C18 C27 C28 -93.35(19) . . . . ? O6 C18 C27 C29 -95.11(17) . . . . ? C16 C18 C27 C29 141.57(16) . . . . ? C30 O10 C29 C27 -132.08(16) . . . . ? C30 O10 C29 C1 101.86(17) . . . . ? C28 C27 C29 O10 37.5(2) . . . . ? C18 C27 C29 O10 161.90(14) . . . . ? C28 C27 C29 C1 162.65(16) . . . . ? C18 C27 C29 C1 -72.95(19) . . . . ? O1 C1 C29 O10 126.79(15) . . . . ? C8 C1 C29 O10 -115.96(17) . . . . ? C2 C1 C29 O10 11.6(2) . . . . ? O1 C1 C29 C27 1.9(2) . . . . ? C8 C1 C29 C27 119.19(17) . . . . ? C2 C1 C29 C27 -113.23(18) . . . . ? C29 O10 C30 O11 -67.70(18) . . . . ? C29 O10 C30 C31 171.63(14) . . . . ? C34 O11 C30 O10 177.96(15) . . . . ? C34 O11 C30 C31 -62.10(19) . . . . ? C35 O12 C31 C30 108.66(18) . . . . ? C35 O12 C31 C32 -132.53(17) . . . . ? O10 C30 C31 O12 -66.86(18) . . . . ? O11 C30 C31 O12 173.93(14) . . . . ? O10 C30 C31 C32 175.66(15) . . . . ? O11 C30 C31 C32 56.44(19) . . . . ? C37 N1 C32 C33 150.81(17) . . . . ? C38 N1 C32 C33 -79.6(2) . . . . ? C37 N1 C32 C31 -83.7(2) . . . . ? C38 N1 C32 C31 45.8(2) . . . . ? O12 C31 C32 N1 64.7(2) . . . . ? C30 C31 C32 N1 -178.88(15) . . . . ? O12 C31 C32 C33 -168.53(14) . . . . ? C30 C31 C32 C33 -52.1(2) . . . . ? N1 C32 C33 C34 -176.50(16) . . . . ? C31 C32 C33 C34 53.6(2) . . . . ? C30 O11 C34 C33 62.4(2) . . . . ? C30 O11 C34 C39 -174.66(16) . . . . ? C32 C33 C34 O11 -58.1(2) . . . . ? C32 C33 C34 C39 -177.07(17) . . . . ? C31 O12 C35 O13 4.8(3) . . . . ? C31 O12 C35 C36 -176.15(17) . . . . ? 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 O1S H1S O8 0.84(3) 2.16(3) 2.9905(18) 172(3) 2_656 O8 H8 N1 0.82 2.11 2.894(2) 158.9 2_756 O3 H3 O1S 0.82 2.25 2.9272(17) 139.6 3_545 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.46 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.253 _refine_diff_density_min -0.162 _refine_diff_density_rms 0.037