# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2010 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_name 'Przybylski, Piotr' _publ_contact_author_email piotrp@amu.edu.pl _publ_section_title ; The influence of protonation on molecular structure and physico-chemical properties of gossypol Schiff bases ; _publ_author_name P.Przybylski data_basia40 _database_code_depnum_ccdc_archive 'CCDC 763715' #TrackingRef '- CheckCIF report and CIF.doc' _audit_creation_method SHELXL-97 _chemical_name_systematic ; (8Z,8'Z)-1,1',6,6'-tetrahydroxy-3,3'-dimethyl-8,8'- bis([3-(morpholin-4-yl)propan-1]amino)- 5,5'-di(propan-2-yl)-2,2'-binaphthalene-7,7'(8H,8'H)-dione ; _chemical_name_common ; (8Z,8'Z)-1,1',6,6'-tetrahydroxy-3,3'-dimethyl-8,8'-bis((3- (morpholin-4-yl)propan-1)amino)-5,5'-di(propan-2-yl)-2,2'-binaphthalene- 7,7'(8H,8'H)-dione ; _chemical_melting_point ? _chemical_formula_moiety 'C44 H58 N4 O8' _chemical_formula_sum 'C44 H58 N4 O8' _chemical_formula_weight 770.94 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 37.523(3) _cell_length_b 11.2668(6) _cell_length_c 21.4820(17) _cell_angle_alpha 90.00 _cell_angle_beta 120.074(10) _cell_angle_gamma 90.00 _cell_volume 7859.2(9) _cell_formula_units_Z 8 _cell_measurement_temperature 105(2) _cell_measurement_reflns_used 449 _cell_measurement_theta_min 2.56 _cell_measurement_theta_max 76.06 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.303 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3312 _exptl_absorpt_coefficient_mu 0.725 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.74578 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; SCALE3 ABSPACK scaling algorithm (Oxford Diffraction, 2007) ; _diffrn_ambient_temperature 105(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'SuperNova (Cu) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'SuperNova, detector: Atlas' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 18723 _diffrn_reflns_av_R_equivalents 0.0321 _diffrn_reflns_av_sigmaI/netI 0.0489 _diffrn_reflns_limit_h_min -44 _diffrn_reflns_limit_h_max 45 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 6.57 _diffrn_reflns_theta_max 68.25 _reflns_number_total 7176 _reflns_number_gt 4387 _reflns_threshold_expression I>2\s(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33 ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33 ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33 ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ; Ortep III for Windows (Farrugia, 1997), Mercury, Version 1.4 (Macrae et al., 2006) ; _computing_publication_material SHELXL-97 _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^)+(0.0823P)^2^] 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_number_reflns 7176 _refine_ls_number_parameters 561 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0842 _refine_ls_R_factor_gt 0.0484 _refine_ls_wR_factor_ref 0.1465 _refine_ls_wR_factor_gt 0.1286 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.032 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.22233(5) 0.52539(14) 0.43483(8) 0.0304(4) Uani 1 1 d . . . H1O H 0.2049 0.5759 0.4118 0.036 Uiso 1 1 calc R . . O3 O 0.34515(4) 0.25031(13) 0.59588(8) 0.0282(4) Uani 1 1 d . . . O4 O 0.33577(5) 0.18847(14) 0.70222(8) 0.0318(4) Uani 1 1 d . . . H4O H 0.3523 0.1710 0.6892 0.038 Uiso 1 1 calc R . . O5 O 0.11240(5) 0.45756(13) 0.36181(8) 0.0312(4) Uani 1 1 d . . . H5O H 0.1317 0.4190 0.3928 0.037 Uiso 1 1 calc R . . O7 O -0.00506(5) 0.69617(15) 0.15388(9) 0.0414(4) Uani 1 1 d . . . O6 O 0.01276(5) 0.91519(14) 0.18046(9) 0.0384(4) Uani 1 1 d . . . H6O H -0.0071 0.8781 0.1498 0.046 Uiso 1 1 calc R . . N1 N 0.32492(5) 0.36737(16) 0.48081(9) 0.0253(4) Uani 1 1 d . . . H1N H 0.3429 0.3236 0.5149 0.030 Uiso 1 1 calc R . . N3 N 0.00800(6) 0.47440(18) 0.17866(11) 0.0401(5) Uani 1 1 d . . . H3N H -0.0075 0.5297 0.1504 0.048 Uiso 1 1 calc R . . C1 C 0.21717(6) 0.48532(19) 0.49015(11) 0.0241(5) Uani 1 1 d . . . C2 C 0.18287(6) 0.52327(19) 0.49387(11) 0.0231(5) Uani 1 1 d . . . C3 C 0.17803(6) 0.48430(19) 0.55129(11) 0.0246(5) Uani 1 1 d . . . C4 C 0.20716(6) 0.41052(19) 0.60187(11) 0.0245(5) Uani 1 1 d . . . H4A H 0.2038 0.3857 0.6399 0.029 Uiso 1 1 calc R . . C5 C 0.27193(6) 0.29203(18) 0.65534(11) 0.0231(5) Uani 1 1 d . . . C6 C 0.30541(6) 0.25735(19) 0.65121(11) 0.0245(5) Uani 1 1 d . . . C7 C 0.31227(6) 0.29156(18) 0.59288(11) 0.0238(5) Uani 1 1 d . . . C8 C 0.28374(6) 0.36737(19) 0.53823(11) 0.0222(5) Uani 1 1 d . . . C9 C 0.24746(6) 0.40849(18) 0.54106(11) 0.0204(5) Uani 1 1 d . . . C10 C 0.24211(6) 0.37009(18) 0.59931(11) 0.0226(5) Uani 1 1 d . . . C11 C 0.11976(6) 0.57702(19) 0.37708(12) 0.0243(5) Uani 1 1 d . . . C12 C 0.15398(6) 0.61153(19) 0.44103(11) 0.0236(5) Uani 1 1 d . . . C13 C 0.16114(7) 0.7339(2) 0.45755(12) 0.0268(5) Uani 1 1 d . . . C14 C 0.13427(7) 0.8144(2) 0.40846(12) 0.0286(5) Uani 1 1 d . . . H14A H 0.1390 0.8947 0.4195 0.034 Uiso 1 1 calc R . . C15 C 0.07420(7) 0.87355(19) 0.29150(12) 0.0263(5) Uani 1 1 d . . . C16 C 0.03999(7) 0.8385(2) 0.23088(12) 0.0299(5) Uani 1 1 d . . . C17 C 0.02850(7) 0.7141(2) 0.21240(12) 0.0304(5) Uani 1 1 d . . . C18 C 0.05487(7) 0.6234(2) 0.25870(12) 0.0282(5) Uani 1 1 d . . . C19 C 0.09156(7) 0.65803(19) 0.32556(12) 0.0249(5) Uani 1 1 d . . . C20 C 0.10001(6) 0.78153(19) 0.34248(12) 0.0243(5) Uani 1 1 d . . . C21 C 0.14185(7) 0.5261(2) 0.55744(13) 0.0333(6) Uani 1 1 d . . . H21A H 0.1431 0.4915 0.5993 0.040 Uiso 1 1 calc R . . H21B H 0.1168 0.5024 0.5154 0.040 Uiso 1 1 calc R . . H21C H 0.1426 0.6110 0.5615 0.040 Uiso 1 1 calc R . . C22 C 0.29204(6) 0.39897(19) 0.48301(11) 0.0247(5) Uani 1 1 d . . . H22A H 0.2727 0.4456 0.4455 0.030 Uiso 1 1 calc R . . C23 C 0.26679(7) 0.25574(19) 0.71859(12) 0.0280(5) Uani 1 1 d . . . H23A H 0.2376 0.2663 0.7031 0.034 Uiso 1 1 calc R . . C24 C 0.29058(9) 0.3400(2) 0.78123(13) 0.0446(7) Uani 1 1 d . . . H24A H 0.3195 0.3341 0.7974 0.054 Uiso 1 1 calc R . . H24B H 0.2859 0.3192 0.8199 0.054 Uiso 1 1 calc R . . H24C H 0.2814 0.4198 0.7660 0.054 Uiso 1 1 calc R . . C25 C 0.27726(7) 0.1263(2) 0.74238(12) 0.0315(6) Uani 1 1 d . . . H25A H 0.3066 0.1164 0.7687 0.038 Uiso 1 1 calc R . . H25B H 0.2656 0.0757 0.7008 0.038 Uiso 1 1 calc R . . H25C H 0.2661 0.1054 0.7726 0.038 Uiso 1 1 calc R . . C26 C 0.19822(7) 0.7735(2) 0.52614(13) 0.0385(6) Uani 1 1 d . . . H26A H 0.2226 0.7599 0.5232 0.046 Uiso 1 1 calc R . . H26B H 0.1999 0.7294 0.5658 0.046 Uiso 1 1 calc R . . H26C H 0.1959 0.8566 0.5333 0.046 Uiso 1 1 calc R . . C27 C 0.04261(7) 0.5059(2) 0.23660(12) 0.0329(6) Uani 1 1 d . . . H27A H 0.0602 0.4457 0.2650 0.039 Uiso 1 1 calc R . . C28 C 0.08620(7) 1.0044(2) 0.30817(13) 0.0340(6) Uani 1 1 d . . . H28A H 0.1162 1.0057 0.3394 0.041 Uiso 1 1 calc R . . C29 C 0.06855(7) 1.0602(2) 0.35169(14) 0.0425(7) Uani 1 1 d . . . H29A H 0.0789 1.1396 0.3651 0.051 Uiso 1 1 calc R . . H29B H 0.0766 1.0139 0.3942 0.051 Uiso 1 1 calc R . . H29C H 0.0390 1.0622 0.3231 0.051 Uiso 1 1 calc R . . C30 C 0.07682(9) 1.0818(2) 0.24346(15) 0.0497(7) Uani 1 1 d . . . H30A H 0.0477 1.0962 0.2158 0.060 Uiso 1 1 calc R . . H30B H 0.0857 1.0418 0.2141 0.060 Uiso 1 1 calc R . . H30C H 0.0911 1.1560 0.2598 0.060 Uiso 1 1 calc R . . O2 O 0.31545(6) 0.19517(17) 0.16906(10) 0.0495(5) Uani 1 1 d . . . N2 N 0.34513(6) 0.31945(18) 0.30145(10) 0.0320(5) Uani 1 1 d . . . C31 C 0.33229(7) 0.4033(2) 0.42291(12) 0.0338(6) Uani 1 1 d . . . H31A H 0.3329 0.4893 0.4213 0.041 Uiso 1 1 calc R . . H31B H 0.3096 0.3761 0.3774 0.041 Uiso 1 1 calc R . . C32 C 0.37183(7) 0.3556(2) 0.43121(12) 0.0349(6) Uani 1 1 d . . . H32A H 0.3727 0.2702 0.4375 0.042 Uiso 1 1 calc R . . H32B H 0.3950 0.3898 0.4736 0.042 Uiso 1 1 calc R . . C33 C 0.37516(7) 0.3854(2) 0.36481(12) 0.0340(6) Uani 1 1 d . . . H33A H 0.3707 0.4698 0.3552 0.041 Uiso 1 1 calc R . . H33B H 0.4027 0.3667 0.3744 0.041 Uiso 1 1 calc R . . C34 C 0.36087(10) 0.2027(2) 0.29811(14) 0.0466(7) Uani 1 1 d . . . H34C H 0.3685 0.1591 0.3420 0.056 Uiso 1 1 calc R . . H34D H 0.3852 0.2114 0.2935 0.056 Uiso 1 1 calc R . . C35 C 0.32819(11) 0.1357(3) 0.23450(16) 0.0635(9) Uani 1 1 d . . . H35A H 0.3388 0.0581 0.2325 0.076 Uiso 1 1 calc R . . H35B H 0.3046 0.1240 0.2408 0.076 Uiso 1 1 calc R . . C36 C 0.30161(8) 0.3127(3) 0.17094(15) 0.0504(8) Uani 1 1 d . . . H36A H 0.2768 0.3086 0.1743 0.060 Uiso 1 1 calc R . . H36B H 0.2950 0.3538 0.1267 0.060 Uiso 1 1 calc R . . C37 C 0.33423(7) 0.3809(2) 0.23414(12) 0.0358(6) Uani 1 1 d . . . H37A H 0.3585 0.3889 0.2294 0.043 Uiso 1 1 calc R . . H37B H 0.3241 0.4598 0.2349 0.043 Uiso 1 1 calc R . . N4 N 0.02326(7) 0.2674(2) 0.05307(13) 0.0547(7) Uani 1 1 d . . . C38 C -0.00581(8) 0.3512(2) 0.15935(14) 0.0451(7) Uani 1 1 d . A . H38A H -0.0223 0.3288 0.1807 0.054 Uiso 1 1 calc R . . H38B H 0.0180 0.2993 0.1787 0.054 Uiso 1 1 calc R . . C39 C -0.03084(8) 0.3353(3) 0.07897(15) 0.0513(8) Uani 1 1 d . . . H39A H -0.0415 0.2549 0.0690 0.062 Uiso 1 1 calc R A . H39B H -0.0542 0.3887 0.0603 0.062 Uiso 1 1 calc R . . C40 C -0.00821(9) 0.3570(3) 0.03863(15) 0.0533(8) Uani 1 1 d . A . H40A H -0.0279 0.3581 -0.0126 0.064 Uiso 1 1 calc R . . H40B H 0.0048 0.4345 0.0518 0.064 Uiso 1 1 calc R . . O8 O 0.10104(17) 0.2159(5) 0.0649(3) 0.0474(13) Uani 0.463(3) 1 d P A 1 C41 C 0.06424(18) 0.3339(6) 0.1092(3) 0.0532(18) Uani 0.463(3) 1 d P A 1 H41A H 0.0675 0.4071 0.0887 0.064 Uiso 0.463(3) 1 calc PR A 1 H41B H 0.0635 0.3527 0.1526 0.064 Uiso 0.463(3) 1 calc PR A 1 C42 C 0.09898(19) 0.2498(6) 0.1255(3) 0.0544(19) Uani 0.463(3) 1 d P A 1 H42A H 0.1248 0.2872 0.1596 0.065 Uiso 0.463(3) 1 calc PR A 1 H42B H 0.0958 0.1793 0.1482 0.065 Uiso 0.463(3) 1 calc PR A 1 C43 C 0.0624(3) 0.1711(11) 0.0138(6) 0.060(3) Uani 0.463(3) 1 d P A 1 H43A H 0.0579 0.0970 0.0318 0.071 Uiso 0.463(3) 1 calc PR A 1 H43D H 0.0629 0.1535 -0.0299 0.071 Uiso 0.463(3) 1 calc PR A 1 C44 C 0.0265(2) 0.2524(7) -0.0047(4) 0.058(2) Uani 0.463(3) 1 d P A 1 H44A H 0.0309 0.3283 -0.0211 0.070 Uiso 0.463(3) 1 calc PR A 1 H44B H 0.0014 0.2179 -0.0430 0.070 Uiso 0.463(3) 1 calc PR A 1 O8' O 0.05706(14) 0.0856(4) -0.0052(3) 0.0689(13) Uani 0.537(3) 1 d P A 2 C41' C 0.0536(2) 0.2884(5) 0.0307(4) 0.0538(16) Uani 0.537(3) 1 d P A 2 H41C H 0.0714 0.3532 0.0589 0.065 Uiso 0.537(3) 1 calc PR A 2 H41D H 0.0393 0.3129 -0.0193 0.065 Uiso 0.537(3) 1 calc PR A 2 C42' C 0.0805(3) 0.1798(10) 0.0390(6) 0.065(3) Uani 0.537(3) 1 d P A 2 H42C H 0.1012 0.2021 0.0268 0.079 Uiso 0.537(3) 1 calc PR A 2 H42D H 0.0946 0.1539 0.0887 0.079 Uiso 0.537(3) 1 calc PR A 2 C43' C 0.02660(19) 0.0506(5) 0.0103(4) 0.0643(18) Uani 0.537(3) 1 d P A 2 H43B H 0.0394 0.0226 0.0595 0.077 Uiso 0.537(3) 1 calc PR A 2 H43C H 0.0109 -0.0143 -0.0211 0.077 Uiso 0.537(3) 1 calc PR A 2 C44' C -0.00227(17) 0.1536(5) 0.0001(3) 0.0554(16) Uani 0.537(3) 1 d P A 2 H44C H -0.0232 0.1270 0.0109 0.066 Uiso 0.537(3) 1 calc PR A 2 H44D H -0.0160 0.1792 -0.0497 0.066 Uiso 0.537(3) 1 calc PR A 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0402(9) 0.0331(10) 0.0277(9) 0.0125(7) 0.0244(8) 0.0112(7) O3 0.0324(8) 0.0256(9) 0.0327(9) 0.0069(7) 0.0209(7) 0.0067(7) O4 0.0374(9) 0.0323(9) 0.0334(9) 0.0105(8) 0.0236(8) 0.0098(7) O5 0.0370(9) 0.0195(8) 0.0325(9) 0.0022(7) 0.0140(7) 0.0044(7) O7 0.0397(10) 0.0334(10) 0.0397(10) 0.0018(8) 0.0114(9) 0.0065(8) O6 0.0393(10) 0.0294(9) 0.0393(11) 0.0079(8) 0.0144(8) 0.0086(8) N1 0.0356(10) 0.0231(10) 0.0242(10) 0.0023(8) 0.0201(8) 0.0050(8) N3 0.0360(11) 0.0291(12) 0.0402(13) 0.0001(10) 0.0081(10) 0.0044(9) C1 0.0345(12) 0.0203(12) 0.0220(11) 0.0005(9) 0.0175(10) -0.0024(9) C2 0.0319(11) 0.0186(11) 0.0248(11) -0.0008(9) 0.0187(10) 0.0002(9) C3 0.0293(11) 0.0228(12) 0.0255(12) -0.0013(10) 0.0165(10) 0.0003(9) C4 0.0330(12) 0.0220(11) 0.0252(12) 0.0010(10) 0.0196(10) -0.0012(9) C5 0.0328(12) 0.0162(11) 0.0238(11) -0.0011(9) 0.0168(10) -0.0011(9) C6 0.0302(11) 0.0200(11) 0.0229(12) 0.0032(9) 0.0130(10) 0.0019(9) C7 0.0297(11) 0.0173(11) 0.0262(12) -0.0011(9) 0.0154(10) -0.0005(9) C8 0.0314(11) 0.0183(11) 0.0228(11) -0.0032(9) 0.0181(10) -0.0010(9) C9 0.0288(11) 0.0159(11) 0.0195(11) -0.0037(9) 0.0142(9) -0.0028(9) C10 0.0323(11) 0.0171(11) 0.0213(11) -0.0027(9) 0.0156(10) -0.0016(9) C11 0.0316(12) 0.0192(11) 0.0297(12) 0.0013(10) 0.0211(10) 0.0005(9) C12 0.0302(11) 0.0223(12) 0.0249(11) 0.0042(9) 0.0187(10) 0.0022(9) C13 0.0322(12) 0.0266(12) 0.0268(12) -0.0016(10) 0.0185(10) 0.0013(10) C14 0.0375(12) 0.0209(12) 0.0334(13) 0.0000(10) 0.0222(11) -0.0012(10) C15 0.0327(12) 0.0230(12) 0.0314(13) 0.0048(10) 0.0221(11) 0.0049(10) C16 0.0376(13) 0.0267(13) 0.0328(13) 0.0070(11) 0.0232(11) 0.0099(10) C17 0.0317(12) 0.0310(14) 0.0318(13) -0.0004(11) 0.0183(11) 0.0038(10) C18 0.0313(12) 0.0256(12) 0.0304(13) 0.0032(10) 0.0176(10) 0.0050(10) C19 0.0348(12) 0.0205(12) 0.0271(12) 0.0007(10) 0.0211(10) 0.0012(9) C20 0.0299(11) 0.0208(12) 0.0306(12) 0.0051(10) 0.0214(10) 0.0033(9) C21 0.0417(13) 0.0335(14) 0.0349(14) 0.0067(11) 0.0269(12) 0.0069(11) C22 0.0325(12) 0.0203(12) 0.0256(12) -0.0022(9) 0.0176(10) 0.0006(9) C23 0.0406(13) 0.0214(12) 0.0302(13) 0.0071(10) 0.0240(11) 0.0040(10) C24 0.085(2) 0.0290(14) 0.0343(14) -0.0012(12) 0.0408(15) -0.0022(14) C25 0.0406(13) 0.0277(13) 0.0341(13) 0.0049(11) 0.0244(11) 0.0019(10) C26 0.0491(15) 0.0243(13) 0.0359(14) -0.0016(11) 0.0166(12) -0.0002(11) C27 0.0366(13) 0.0275(13) 0.0334(14) 0.0031(11) 0.0167(11) 0.0040(10) C28 0.0396(13) 0.0228(13) 0.0424(15) 0.0044(11) 0.0226(12) 0.0047(10) C29 0.0437(15) 0.0296(14) 0.0598(18) -0.0098(13) 0.0302(14) -0.0042(11) C30 0.0608(17) 0.0304(15) 0.0583(18) 0.0125(14) 0.0302(15) 0.0010(13) O2 0.0685(12) 0.0526(13) 0.0475(12) -0.0255(10) 0.0440(10) -0.0254(10) N2 0.0413(11) 0.0332(12) 0.0328(11) -0.0092(9) 0.0270(10) -0.0093(9) C31 0.0463(14) 0.0371(14) 0.0304(13) 0.0089(11) 0.0284(12) 0.0094(12) C32 0.0361(13) 0.0453(16) 0.0290(13) -0.0047(12) 0.0207(11) -0.0026(11) C33 0.0380(13) 0.0403(15) 0.0317(13) -0.0098(11) 0.0235(11) -0.0090(11) C34 0.089(2) 0.0279(14) 0.0429(16) 0.0000(12) 0.0478(16) -0.0014(14) C35 0.121(3) 0.0380(17) 0.073(2) -0.0186(16) 0.079(2) -0.0315(18) C36 0.0429(15) 0.069(2) 0.0433(16) -0.0211(15) 0.0250(13) -0.0008(14) C37 0.0439(14) 0.0377(15) 0.0332(14) -0.0054(12) 0.0248(12) 0.0046(12) N4 0.0516(14) 0.0662(18) 0.0539(16) 0.0254(14) 0.0321(13) 0.0143(13) C38 0.0428(15) 0.0303(15) 0.0533(17) -0.0081(13) 0.0174(13) -0.0050(12) C39 0.0426(15) 0.0443(17) 0.0540(18) -0.0154(14) 0.0145(14) -0.0013(13) C40 0.0614(18) 0.0429(18) 0.0448(17) 0.0032(14) 0.0185(15) -0.0008(15) O8 0.050(3) 0.054(3) 0.047(3) -0.006(2) 0.031(3) -0.004(2) C41 0.047(3) 0.075(5) 0.037(3) -0.006(3) 0.021(3) 0.003(3) C42 0.050(4) 0.076(5) 0.040(4) -0.012(3) 0.024(3) -0.003(3) C43 0.033(6) 0.070(7) 0.064(7) -0.026(5) 0.015(5) 0.003(6) C44 0.058(4) 0.067(5) 0.047(4) -0.011(4) 0.024(4) 0.007(4) O8' 0.076(3) 0.052(3) 0.094(3) -0.014(3) 0.053(3) -0.006(2) C41' 0.066(4) 0.051(4) 0.055(4) -0.002(3) 0.039(3) -0.011(3) C42' 0.027(6) 0.091(7) 0.077(9) 0.001(6) 0.025(6) -0.004(6) C43' 0.073(4) 0.047(4) 0.096(5) -0.006(3) 0.060(4) -0.001(3) C44' 0.061(3) 0.045(3) 0.067(4) -0.009(3) 0.037(3) -0.006(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.373(2) . ? O1 H1O 0.8200 . ? O3 C7 1.289(2) . ? O4 C6 1.360(2) . ? O4 H4O 0.8200 . ? O5 C11 1.380(3) . ? O5 H5O 0.8200 . ? O7 C17 1.273(3) . ? O6 C16 1.362(3) . ? O6 H6O 0.8200 . ? N1 C22 1.308(3) . ? N1 C31 1.460(3) . ? N1 H1N 0.8600 . ? N3 C27 1.320(3) . ? N3 C38 1.466(3) . ? N3 H3N 0.8600 . ? C1 C2 1.396(3) . ? C1 C9 1.411(3) . ? C2 C3 1.404(3) . ? C2 C12 1.490(3) . ? C3 C4 1.370(3) . ? C3 C21 1.504(3) . ? C4 C10 1.415(3) . ? C4 H4A 0.9300 . ? C5 C6 1.360(3) . ? C5 C10 1.458(3) . ? C5 C23 1.521(3) . ? C6 C7 1.452(3) . ? C7 C8 1.412(3) . ? C8 C22 1.415(3) . ? C8 C9 1.468(3) . ? C9 C10 1.430(3) . ? C11 C12 1.385(3) . ? C11 C19 1.416(3) . ? C12 C13 1.416(3) . ? C13 C14 1.373(3) . ? C13 C26 1.500(3) . ? C14 C20 1.404(3) . ? C14 H14A 0.9300 . ? C15 C16 1.351(3) . ? C15 C20 1.466(3) . ? C15 C28 1.530(3) . ? C16 C17 1.462(3) . ? C17 C18 1.423(3) . ? C18 C27 1.404(3) . ? C18 C19 1.459(3) . ? C19 C20 1.433(3) . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C22 H22A 0.9300 . ? C23 C24 1.518(3) . ? C23 C25 1.530(3) . ? C23 H23A 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 H27A 0.9300 . ? C28 C30 1.525(3) . ? C28 C29 1.526(3) . ? C28 H28A 0.9800 . ? C29 H29A 0.9600 . ? C29 H29B 0.9600 . ? C29 H29C 0.9600 . ? C30 H30A 0.9600 . ? C30 H30B 0.9600 . ? C30 H30C 0.9600 . ? O2 C35 1.407(3) . ? O2 C36 1.431(3) . ? N2 C34 1.459(3) . ? N2 C33 1.462(3) . ? N2 C37 1.465(3) . ? C31 C32 1.502(3) . ? C31 H31A 0.9700 . ? C31 H31B 0.9700 . ? C32 C33 1.530(3) . ? C32 H32A 0.9700 . ? C32 H32B 0.9700 . ? C33 H33A 0.9700 . ? C33 H33B 0.9700 . ? C34 C35 1.504(4) . ? C34 H34C 0.9700 . ? C34 H34D 0.9700 . ? C35 H35A 0.9700 . ? C35 H35B 0.9700 . ? C36 C37 1.505(3) . ? C36 H36A 0.9700 . ? C36 H36B 0.9700 . ? C37 H37A 0.9700 . ? C37 H37B 0.9700 . ? N4 C44 1.318(7) . ? N4 C41' 1.461(6) . ? N4 C40 1.464(4) . ? N4 C41 1.588(6) . ? N4 C44' 1.663(6) . ? C38 C39 1.507(3) . ? C38 H38A 0.9700 . ? C38 H38B 0.9700 . ? C39 C40 1.507(4) . ? C39 H39A 0.9700 . ? C39 H39B 0.9700 . ? C40 H40A 0.9700 . ? C40 H40B 0.9700 . ? O8 C42 1.396(7) . ? O8 C43 1.402(9) . ? C41 C42 1.504(8) . ? C41 H41A 0.9700 . ? C41 H41B 0.9700 . ? C42 H42A 0.9700 . ? C42 H42B 0.9700 . ? C43 C44 1.508(12) . ? C43 H43A 0.9700 . ? C43 H43D 0.9700 . ? C44 H44A 0.9700 . ? C44 H44B 0.9700 . ? O8' C43' 1.398(6) . ? O8' C42' 1.401(10) . ? C41' C42' 1.538(11) . ? C41' H41C 0.9700 . ? C41' H41D 0.9700 . ? C42' H42C 0.9700 . ? C42' H42D 0.9700 . ? C43' C44' 1.526(7) . ? C43' H43B 0.9700 . ? C43' H43C 0.9700 . ? C44' H44C 0.9700 . ? C44' H44D 0.9700 . ? 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 C1 O1 H1O 109.5 . . ? C6 O4 H4O 109.5 . . ? C11 O5 H5O 109.5 . . ? C16 O6 H6O 109.5 . . ? C22 N1 C31 122.70(18) . . ? C22 N1 H1N 118.7 . . ? C31 N1 H1N 118.7 . . ? C27 N3 C38 124.2(2) . . ? C27 N3 H3N 117.9 . . ? C38 N3 H3N 117.9 . . ? O1 C1 C2 118.88(19) . . ? O1 C1 C9 117.68(18) . . ? C2 C1 C9 123.4(2) . . ? C1 C2 C3 118.90(19) . . ? C1 C2 C12 120.04(19) . . ? C3 C2 C12 120.86(19) . . ? C4 C3 C2 118.9(2) . . ? C4 C3 C21 121.1(2) . . ? C2 C3 C21 119.94(19) . . ? C3 C4 C10 123.5(2) . . ? C3 C4 H4A 118.3 . . ? C10 C4 H4A 118.3 . . ? C6 C5 C10 118.13(19) . . ? C6 C5 C23 121.05(19) . . ? C10 C5 C23 120.74(19) . . ? C5 C6 O4 122.7(2) . . ? C5 C6 C7 123.30(19) . . ? O4 C6 C7 114.04(18) . . ? O3 C7 C8 124.6(2) . . ? O3 C7 C6 116.12(19) . . ? C8 C7 C6 119.32(19) . . ? C7 C8 C22 117.11(19) . . ? C7 C8 C9 119.26(19) . . ? C22 C8 C9 123.63(19) . . ? C1 C9 C10 116.88(19) . . ? C1 C9 C8 124.40(19) . . ? C10 C9 C8 118.72(18) . . ? C4 C10 C9 118.41(19) . . ? C4 C10 C5 120.34(19) . . ? C9 C10 C5 121.25(19) . . ? O5 C11 C12 119.02(19) . . ? O5 C11 C19 117.44(19) . . ? C12 C11 C19 123.5(2) . . ? C11 C12 C13 119.2(2) . . ? C11 C12 C2 121.81(19) . . ? C13 C12 C2 119.01(19) . . ? C14 C13 C12 118.5(2) . . ? C14 C13 C26 121.4(2) . . ? C12 C13 C26 120.1(2) . . ? C13 C14 C20 123.3(2) . . ? C13 C14 H14A 118.3 . . ? C20 C14 H14A 118.3 . . ? C16 C15 C20 117.8(2) . . ? C16 C15 C28 122.2(2) . . ? C20 C15 C28 119.97(19) . . ? C15 C16 O6 123.6(2) . . ? C15 C16 C17 123.4(2) . . ? O6 C16 C17 113.0(2) . . ? O7 C17 C18 125.0(2) . . ? O7 C17 C16 115.6(2) . . ? C18 C17 C16 119.4(2) . . ? C27 C18 C17 116.4(2) . . ? C27 C18 C19 124.9(2) . . ? C17 C18 C19 118.6(2) . . ? C11 C19 C20 116.36(19) . . ? C11 C19 C18 124.4(2) . . ? C20 C19 C18 119.26(19) . . ? C14 C20 C19 119.1(2) . . ? C14 C20 C15 119.7(2) . . ? C19 C20 C15 121.2(2) . . ? C3 C21 H21A 109.5 . . ? C3 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C3 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? N1 C22 C8 124.7(2) . . ? N1 C22 H22A 117.6 . . ? C8 C22 H22A 117.6 . . ? C24 C23 C5 110.01(18) . . ? C24 C23 C25 111.18(19) . . ? C5 C23 C25 115.35(18) . . ? C24 C23 H23A 106.6 . . ? C5 C23 H23A 106.6 . . ? C25 C23 H23A 106.6 . . ? C23 C24 H24A 109.5 . . ? C23 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C23 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C23 C25 H25A 109.5 . . ? C23 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C23 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C13 C26 H26A 109.5 . . ? C13 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C13 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? N3 C27 C18 125.0(2) . . ? N3 C27 H27A 117.5 . . ? C18 C27 H27A 117.5 . . ? C30 C28 C29 110.5(2) . . ? C30 C28 C15 115.5(2) . . ? C29 C28 C15 111.91(19) . . ? C30 C28 H28A 106.1 . . ? C29 C28 H28A 106.1 . . ? C15 C28 H28A 106.1 . . ? C28 C29 H29A 109.5 . . ? C28 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C28 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C28 C30 H30A 109.5 . . ? C28 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C28 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? C35 O2 C36 111.0(2) . . ? C34 N2 C33 111.22(19) . . ? C34 N2 C37 107.29(18) . . ? C33 N2 C37 112.49(18) . . ? N1 C31 C32 113.38(19) . . ? N1 C31 H31A 108.9 . . ? C32 C31 H31A 108.9 . . ? N1 C31 H31B 108.9 . . ? C32 C31 H31B 108.9 . . ? H31A C31 H31B 107.7 . . ? C31 C32 C33 110.3(2) . . ? C31 C32 H32A 109.6 . . ? C33 C32 H32A 109.6 . . ? C31 C32 H32B 109.6 . . ? C33 C32 H32B 109.6 . . ? H32A C32 H32B 108.1 . . ? N2 C33 C32 111.79(19) . . ? N2 C33 H33A 109.3 . . ? C32 C33 H33A 109.3 . . ? N2 C33 H33B 109.3 . . ? C32 C33 H33B 109.3 . . ? H33A C33 H33B 107.9 . . ? N2 C34 C35 109.4(2) . . ? N2 C34 H34C 109.8 . . ? C35 C34 H34C 109.8 . . ? N2 C34 H34D 109.8 . . ? C35 C34 H34D 109.8 . . ? H34C C34 H34D 108.3 . . ? O2 C35 C34 112.5(2) . . ? O2 C35 H35A 109.1 . . ? C34 C35 H35A 109.1 . . ? O2 C35 H35B 109.1 . . ? C34 C35 H35B 109.1 . . ? H35A C35 H35B 107.8 . . ? O2 C36 C37 110.8(2) . . ? O2 C36 H36A 109.5 . . ? C37 C36 H36A 109.5 . . ? O2 C36 H36B 109.5 . . ? C37 C36 H36B 109.5 . . ? H36A C36 H36B 108.1 . . ? N2 C37 C36 110.4(2) . . ? N2 C37 H37A 109.6 . . ? C36 C37 H37A 109.6 . . ? N2 C37 H37B 109.6 . . ? C36 C37 H37B 109.6 . . ? H37A C37 H37B 108.1 . . ? C44 N4 C41' 41.8(4) . . ? C44 N4 C40 109.6(4) . . ? C41' N4 C40 119.9(3) . . ? C44 N4 C41 105.3(5) . . ? C41' N4 C41 63.6(4) . . ? C40 N4 C41 101.9(3) . . ? C44 N4 C44' 63.2(4) . . ? C41' N4 C44' 100.1(4) . . ? C40 N4 C44' 105.1(3) . . ? C41 N4 C44' 152.9(3) . . ? N3 C38 C39 111.5(2) . . ? N3 C38 H38A 109.3 . . ? C39 C38 H38A 109.3 . . ? N3 C38 H38B 109.3 . . ? C39 C38 H38B 109.3 . . ? H38A C38 H38B 108.0 . . ? C40 C39 C38 115.6(2) . . ? C40 C39 H39A 108.4 . . ? C38 C39 H39A 108.4 . . ? C40 C39 H39B 108.4 . . ? C38 C39 H39B 108.4 . . ? H39A C39 H39B 107.4 . . ? N4 C40 C39 113.2(2) . . ? N4 C40 H40A 108.9 . . ? C39 C40 H40A 108.9 . . ? N4 C40 H40B 108.9 . . ? C39 C40 H40B 108.9 . . ? H40A C40 H40B 107.8 . . ? C42 O8 C43 108.0(7) . . ? C42 C41 N4 106.0(5) . . ? C42 C41 H41A 110.5 . . ? N4 C41 H41A 110.5 . . ? C42 C41 H41B 110.5 . . ? N4 C41 H41B 110.5 . . ? H41A C41 H41B 108.7 . . ? O8 C42 C41 113.7(5) . . ? O8 C42 H42A 108.8 . . ? C41 C42 H42A 108.8 . . ? O8 C42 H42B 108.8 . . ? C41 C42 H42B 108.8 . . ? H42A C42 H42B 107.7 . . ? O8 C43 C44 115.1(9) . . ? O8 C43 H43A 108.5 . . ? C44 C43 H43A 108.5 . . ? O8 C43 H43D 108.5 . . ? C44 C43 H43D 108.5 . . ? H43A C43 H43D 107.5 . . ? N4 C44 C43 108.8(7) . . ? N4 C44 H44A 109.9 . . ? C43 C44 H44A 109.9 . . ? N4 C44 H44B 109.9 . . ? C43 C44 H44B 109.9 . . ? H44A C44 H44B 108.3 . . ? C43' O8' C42' 111.2(6) . . ? N4 C41' C42' 114.0(5) . . ? N4 C41' H41C 108.7 . . ? C42' C41' H41C 108.7 . . ? N4 C41' H41D 108.7 . . ? C42' C41' H41D 108.7 . . ? H41C C41' H41D 107.6 . . ? O8' C42' C41' 111.9(7) . . ? O8' C42' H42C 109.2 . . ? C41' C42' H42C 109.2 . . ? O8' C42' H42D 109.2 . . ? C41' C42' H42D 109.2 . . ? H42C C42' H42D 107.9 . . ? O8' C43' C44' 111.0(5) . . ? O8' C43' H43B 109.4 . . ? C44' C43' H43B 109.4 . . ? O8' C43' H43C 109.4 . . ? C44' C43' H43C 109.4 . . ? H43B C43' H43C 108.0 . . ? C43' C44' N4 111.4(4) . . ? C43' C44' H44C 109.4 . . ? N4 C44' H44C 109.4 . . ? C43' C44' H44D 109.4 . . ? N4 C44' H44D 109.4 . . ? H44C C44' H44D 108.0 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 C3 -178.67(19) . . . . ? C9 C1 C2 C3 0.5(3) . . . . ? O1 C1 C2 C12 -3.7(3) . . . . ? C9 C1 C2 C12 175.4(2) . . . . ? C1 C2 C3 C4 0.1(3) . . . . ? C12 C2 C3 C4 -174.8(2) . . . . ? C1 C2 C3 C21 178.6(2) . . . . ? C12 C2 C3 C21 3.7(3) . . . . ? C2 C3 C4 C10 -0.5(3) . . . . ? C21 C3 C4 C10 -179.0(2) . . . . ? C10 C5 C6 O4 177.38(19) . . . . ? C23 C5 C6 O4 0.5(3) . . . . ? C10 C5 C6 C7 -1.7(3) . . . . ? C23 C5 C6 C7 -178.6(2) . . . . ? C5 C6 C7 O3 -179.0(2) . . . . ? O4 C6 C7 O3 1.8(3) . . . . ? C5 C6 C7 C8 1.9(3) . . . . ? O4 C6 C7 C8 -177.29(19) . . . . ? O3 C7 C8 C22 0.4(3) . . . . ? C6 C7 C8 C22 179.40(19) . . . . ? O3 C7 C8 C9 -179.87(19) . . . . ? C6 C7 C8 C9 -0.9(3) . . . . ? O1 C1 C9 C10 178.45(18) . . . . ? C2 C1 C9 C10 -0.7(3) . . . . ? O1 C1 C9 C8 -0.9(3) . . . . ? C2 C1 C9 C8 180.0(2) . . . . ? C7 C8 C9 C1 179.2(2) . . . . ? C22 C8 C9 C1 -1.1(3) . . . . ? C7 C8 C9 C10 -0.1(3) . . . . ? C22 C8 C9 C10 179.6(2) . . . . ? C3 C4 C10 C9 0.2(3) . . . . ? C3 C4 C10 C5 179.7(2) . . . . ? C1 C9 C10 C4 0.3(3) . . . . ? C8 C9 C10 C4 179.72(19) . . . . ? C1 C9 C10 C5 -179.12(19) . . . . ? C8 C9 C10 C5 0.3(3) . . . . ? C6 C5 C10 C4 -178.80(19) . . . . ? C23 C5 C10 C4 -1.9(3) . . . . ? C6 C5 C10 C9 0.6(3) . . . . ? C23 C5 C10 C9 177.56(19) . . . . ? O5 C11 C12 C13 -178.69(19) . . . . ? C19 C11 C12 C13 1.6(3) . . . . ? O5 C11 C12 C2 -0.3(3) . . . . ? C19 C11 C12 C2 179.90(19) . . . . ? C1 C2 C12 C11 91.3(3) . . . . ? C3 C2 C12 C11 -93.9(3) . . . . ? C1 C2 C12 C13 -90.4(3) . . . . ? C3 C2 C12 C13 84.5(3) . . . . ? C11 C12 C13 C14 -1.5(3) . . . . ? C2 C12 C13 C14 -179.94(19) . . . . ? C11 C12 C13 C26 -179.4(2) . . . . ? C2 C12 C13 C26 2.2(3) . . . . ? C12 C13 C14 C20 -0.1(3) . . . . ? C26 C13 C14 C20 177.7(2) . . . . ? C20 C15 C16 O6 177.8(2) . . . . ? C28 C15 C16 O6 -1.7(3) . . . . ? C20 C15 C16 C17 -2.7(3) . . . . ? C28 C15 C16 C17 177.9(2) . . . . ? C15 C16 C17 O7 178.9(2) . . . . ? O6 C16 C17 O7 -1.5(3) . . . . ? C15 C16 C17 C18 -2.0(3) . . . . ? O6 C16 C17 C18 177.60(19) . . . . ? O7 C17 C18 C27 0.9(3) . . . . ? C16 C17 C18 C27 -178.1(2) . . . . ? O7 C17 C18 C19 -177.5(2) . . . . ? C16 C17 C18 C19 3.4(3) . . . . ? O5 C11 C19 C20 -179.64(18) . . . . ? C12 C11 C19 C20 0.1(3) . . . . ? O5 C11 C19 C18 1.7(3) . . . . ? C12 C11 C19 C18 -178.6(2) . . . . ? C27 C18 C19 C11 0.1(4) . . . . ? C17 C18 C19 C11 178.4(2) . . . . ? C27 C18 C19 C20 -178.5(2) . . . . ? C17 C18 C19 C20 -0.2(3) . . . . ? C13 C14 C20 C19 1.8(3) . . . . ? C13 C14 C20 C15 -176.7(2) . . . . ? C11 C19 C20 C14 -1.7(3) . . . . ? C18 C19 C20 C14 177.00(19) . . . . ? C11 C19 C20 C15 176.69(19) . . . . ? C18 C19 C20 C15 -4.6(3) . . . . ? C16 C15 C20 C14 -175.6(2) . . . . ? C28 C15 C20 C14 3.9(3) . . . . ? C16 C15 C20 C19 6.0(3) . . . . ? C28 C15 C20 C19 -174.5(2) . . . . ? C31 N1 C22 C8 -179.4(2) . . . . ? C7 C8 C22 N1 -3.2(3) . . . . ? C9 C8 C22 N1 177.14(19) . . . . ? C6 C5 C23 C24 83.5(3) . . . . ? C10 C5 C23 C24 -93.3(2) . . . . ? C6 C5 C23 C25 -43.2(3) . . . . ? C10 C5 C23 C25 139.9(2) . . . . ? C38 N3 C27 C18 -175.1(2) . . . . ? C17 C18 C27 N3 -3.3(4) . . . . ? C19 C18 C27 N3 175.0(2) . . . . ? C16 C15 C28 C30 -36.3(3) . . . . ? C20 C15 C28 C30 144.2(2) . . . . ? C16 C15 C28 C29 91.3(3) . . . . ? C20 C15 C28 C29 -88.2(3) . . . . ? C22 N1 C31 C32 -179.4(2) . . . . ? N1 C31 C32 C33 173.85(19) . . . . ? C34 N2 C33 C32 -85.9(2) . . . . ? C37 N2 C33 C32 153.7(2) . . . . ? C31 C32 C33 N2 -69.0(3) . . . . ? C33 N2 C34 C35 176.9(2) . . . . ? C37 N2 C34 C35 -59.6(3) . . . . ? C36 O2 C35 C34 -55.7(3) . . . . ? N2 C34 C35 O2 58.9(3) . . . . ? C35 O2 C36 C37 55.0(3) . . . . ? C34 N2 C37 C36 60.4(3) . . . . ? C33 N2 C37 C36 -176.9(2) . . . . ? O2 C36 C37 N2 -58.4(3) . . . . ? C27 N3 C38 C39 -149.2(2) . . . . ? N3 C38 C39 C40 63.8(3) . . . . ? C44 N4 C40 C39 148.0(5) . . . . ? C41' N4 C40 C39 -167.1(4) . . . . ? C41 N4 C40 C39 -100.8(3) . . . . ? C44' N4 C40 C39 81.5(3) . . . . ? C38 C39 C40 N4 68.5(3) . . . . ? C44 N4 C41 C42 -63.5(6) . . . . ? C41' N4 C41 C42 -60.3(5) . . . . ? C40 N4 C41 C42 -177.9(4) . . . . ? C44' N4 C41 C42 -2.9(10) . . . . ? C43 O8 C42 C41 -53.7(9) . . . . ? N4 C41 C42 O8 58.3(7) . . . . ? C42 O8 C43 C44 53.6(12) . . . . ? C41' N4 C44 C43 60.0(7) . . . . ? C40 N4 C44 C43 173.3(6) . . . . ? C41 N4 C44 C43 64.3(8) . . . . ? C44' N4 C44 C43 -89.3(7) . . . . ? O8 C43 C44 N4 -64.3(12) . . . . ? C44 N4 C41' C42' -84.8(8) . . . . ? C40 N4 C41' C42' -171.2(5) . . . . ? C41 N4 C41' C42' 99.8(7) . . . . ? C44' N4 C41' C42' -57.2(7) . . . . ? C43' O8' C42' C41' -58.7(9) . . . . ? N4 C41' C42' O8' 63.4(9) . . . . ? C42' O8' C43' C44' 58.9(7) . . . . ? O8' C43' C44' N4 -59.3(6) . . . . ? C44 N4 C44' C43' 76.6(5) . . . . ? C41' N4 C44' C43' 56.3(5) . . . . ? C40 N4 C44' C43' -178.8(4) . . . . ? C41 N4 C44' C43' 6.3(10) . . . . ? 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 O1 H1O O2 0.82 2.02 2.735(2) 145 4 O4 H4O O3 0.82 2.09 2.575(2) 118 . O4 H4O O5 0.82 2.55 3.326(2) 158 7_556 O5 H5O O3 0.82 2.06 2.720(2) 137 7_556 O6 H6O O7 0.82 2.05 2.546(2) 118 . N1 H1N O3 0.86 1.89 2.559(2) 133 . N3 H3N O7 0.86 1.88 2.551(3) 134 . _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 68.25 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.251 _refine_diff_density_min -0.272 _refine_diff_density_rms 0.051