Supplementary Material (ESI) for Dalton Transactions This journal is (c) The Royal Society of Chemistry 2003 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Leonard F. Lindoy' _publ_contact_author_address ; The Centre for Heavy Metal Research, School of Chemistry, University of Sydney, Sydney 2006, NSW, Australia. ; _publ_contact_author_email Lindoy@chem.usyd.edu.au _publ_contact_author_fax '+61 2 9351 3329' _publ_contact_author_phone '+61 2 9351 4400' _publ_section_title ; Host-guest assembly of ligand systems for metal ion complexation; synergistic solvent extraction of copper(II) ions by N3O2-donor macrocycles and carboxylic or phosphinic acids ; loop_ _publ_author_name _publ_author_address 'Karl A. Byriel' ; Department of Chemistry, The University of Queensland, Brisbane, Qld, 4072 ; 'Vesna Gasperov' ; Centre for Heavy Metals Research, School of Chemistry F11, University of Sydney, N.S.W., 2006, Australia ; 'Karsten Gloe' ; Institute of Inorganic Chemistry, Technical University Dresden, 01062 Dresden, Germany ; 'Colin H. L. Kennard' ; Department of Chemistry, The University of Queensland, Brisbane, Qld, 4072 ; 'Anthony J. Leong' ; School of Pharmacy and Molecular Sciences, James Cook University, Townsville, Qld.,4811, Australia ; ; L.F.Lindoy ; ; Centre for Heavy Metals Research, School of Chemistry F11, University of Sydney, N.S.W., 2006, Australia ; 'Myrna S. Mahinay' ; School of Pharmacy and Molecular Sciences, James Cook University, Townsville, Qld.,4811, Australia ; 'Huong T. Pham' ; Centre for Heavy Metals Research, School of Chemistry F11, University of Sydney, N.S.W., 2006, Australia ; 'Peter A. Tasker' ; Chemistry Department, University of Edinburgh, Kings Buildings, West Mains Road, Edinburgh EH9 3JJ, U.K. ; 'Derek Thorp' ; Avecia, P.O. Box 42, Hexagon House, Blackley, Manchester M9 3DA, U.K. ; 'Peter Turner' ; Crystal Structure Analysis Facility, School of Chemistry F11, University of Sydney, N.S.W., 2006, Australia ; #======================================================================= # Data block for single structure (one for each study in the paper) #======================================================================= data_164ma312 _database_code_CSD 207755 _audit_creation_date 2003-02-21T12:07:13-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.1 _audit_conform_dict_location ftp://ftp.iucr.org/cifdics/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_sum 'C44 H62 N4 O8' _chemical_formula_weight 774.98 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n ' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, z+1/2' '-x, -y, -z' '-x-1/2, y-1/2, -z-1/2' _cell_length_a 17.606(2) _cell_length_b 15.587(2) _cell_length_c 18.288(2) _cell_angle_alpha 90 _cell_angle_beta 118.01(2) _cell_angle_gamma 90 _cell_volume 4430.9(9) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_density_diffrn 1.162 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1672 _exptl_crystal_description lathe _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.08 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.08 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_reflns_number 8173 _diffrn_reflns_av_R_equivalents 0.0335 _diffrn_reflns_av_unetI/netI 0.121 _diffrn_reflns_limit_h_min -2 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.32 _diffrn_reflns_theta_max 24.98 _diffrn_reflns_theta_full 24.98 _diffrn_measured_fraction_theta_full 1 _diffrn_measured_fraction_theta_max 1 _reflns_number_total 7783 _reflns_number_gt 2540 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0721P)^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 mixed _refine_ls_extinction_method none _refine_ls_number_reflns 7783 _refine_ls_number_parameters 517 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2166 _refine_ls_R_factor_gt 0.0413 _refine_ls_wR_factor_ref 0.1564 _refine_ls_wR_factor_gt 0.1045 _refine_ls_goodness_of_fit_ref 0.95 _refine_ls_restrained_S_all 0.95 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.24 _refine_diff_density_min -0.187 _refine_diff_density_rms 0.038 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 N1 N 0.78568(15) 0.16992(16) 0.37920(15) 0.0510(7) Uani 1 1 d . . . H1A H 0.7504 0.194 0.33 0.061 Uiso 1 1 calc R . . H1B H 0.7835 0.2021 0.419 0.061 Uiso 1 1 calc R . . C2 C 0.8750(2) 0.1712(2) 0.3907(2) 0.0615(10) Uani 1 1 d . . . H2A H 0.8838 0.1219 0.3631 0.074 Uiso 1 1 calc R . . H2B H 0.9154 0.1671 0.4493 0.074 Uiso 1 1 calc R . . C3 C 0.8921(2) 0.2517(2) 0.3562(2) 0.0645(10) Uani 1 1 d . . . H3A H 0.8865 0.3009 0.3859 0.077 Uiso 1 1 calc R . . H3B H 0.9504 0.2507 0.3637 0.077 Uiso 1 1 calc R . . N4 N 0.83153(16) 0.25947(17) 0.26861(16) 0.0550(7) Uani 1 1 d . . . H4 H 0.8386 0.203 0.2387 0.110(13) Uiso 1 1 d R . . C5 C 0.8390(2) 0.3426(2) 0.2360(2) 0.0642(10) Uani 1 1 d . . . H5A H 0.8947 0.3473 0.2377 0.077 Uiso 1 1 calc R . . H5B H 0.8343 0.3881 0.2698 0.077 Uiso 1 1 calc R . . C6 C 0.7689(2) 0.3514(2) 0.1484(2) 0.0596(9) Uani 1 1 d . . . H6A H 0.7749 0.4058 0.1259 0.072 Uiso 1 1 calc R . . H6B H 0.7742 0.3059 0.1148 0.072 Uiso 1 1 calc R . . N7 N 0.68262(16) 0.34681(16) 0.14431(15) 0.0552(7) Uani 1 1 d . . . H7A H 0.6772 0.3913 0.1729 0.066 Uiso 1 1 calc R . . H7B H 0.6796 0.2983 0.1695 0.066 Uiso 1 1 calc R . . C8 C 0.6085(2) 0.3484(2) 0.0583(2) 0.0602(9) Uani 1 1 d . . . H8A H 0.5553 0.3411 0.0612 0.072 Uiso 1 1 calc R . . H8B H 0.6065 0.4039 0.0335 0.072 Uiso 1 1 calc R . . O11 O 0.58929(14) 0.17902(14) 0.08423(12) 0.0570(6) Uani 1 1 d . . . C12 C 0.5594(2) 0.0948(2) 0.0909(2) 0.0631(10) Uani 1 1 d . . . H12A H 0.6055 0.0533 0.106 0.076 Uiso 1 1 calc R . . H12B H 0.5121 0.0778 0.0381 0.076 Uiso 1 1 calc R . . C13 C 0.5305(2) 0.0967(2) 0.15546(19) 0.0646(10) Uani 1 1 d . . . H13A H 0.4973(8) 0.1534(12) 0.1510(2) 0.078 Uiso 1 1 calc R . . H13B H 0.4894(9) 0.0452(11) 0.1472(3) 0.078 Uiso 1 1 calc R . . O14 O 0.60496(13) 0.09112(14) 0.23507(13) 0.0601(6) Uani 1 1 d . . . C17 C 0.7539(2) 0.0822(2) 0.3821(2) 0.0556(9) Uani 1 1 d . . . H17A H 0.7947 0.0542 0.4328 0.067 Uiso 1 1 calc R . . H17B H 0.7511 0.0491 0.3359 0.067 Uiso 1 1 calc R . . C9 C 0.6150(2) 0.2795(2) 0.00432(19) 0.0508(8) Uani 1 1 d . . . C21 C 0.6314(2) 0.2999(2) -0.0601(2) 0.0643(10) Uani 1 1 d . . . H21 H 0.6401 0.3569 -0.0691 0.077 Uiso 1 1 calc R . . C22 C 0.6349(2) 0.2370(3) -0.1118(2) 0.0713(11) Uani 1 1 d . . . H22 H 0.646 0.2515 -0.1553 0.086 Uiso 1 1 calc R . . C23 C 0.6220(2) 0.1529(3) -0.0982(2) 0.0660(10) Uani 1 1 d . . . H23 H 0.6237 0.1105 -0.1332 0.079 Uiso 1 1 calc R . . C24 C 0.6064(2) 0.1300(2) -0.03381(19) 0.0559(9) Uani 1 1 d . . . H24 H 0.5981 0.0728 -0.025 0.067 Uiso 1 1 calc R . . C10 C 0.60331(19) 0.1939(2) 0.01811(18) 0.0499(8) Uani 1 1 d . . . C15 C 0.5925(2) 0.0861(2) 0.30299(19) 0.0494(8) Uani 1 1 d . . . C31 C 0.5130(2) 0.0853(2) 0.3007(2) 0.0644(10) Uani 1 1 d . . . H31 H 0.4631 0.0883 0.2502 0.077 Uiso 1 1 calc R . . C32 C 0.5077(3) 0.0802(3) 0.3735(3) 0.0754(11) Uani 1 1 d . . . H32 H 0.454 0.0798 0.3718 0.09 Uiso 1 1 calc R . . C33 C 0.5801(3) 0.0759(2) 0.4477(2) 0.0772(11) Uani 1 1 d . . . H33 H 0.5762 0.0718 0.4966 0.093 Uiso 1 1 calc R . . C34 C 0.6599(3) 0.0774(2) 0.4498(2) 0.0681(10) Uani 1 1 d . . . H34 H 0.7095 0.0753 0.5005 0.082 Uiso 1 1 calc R . . C16 C 0.6668(2) 0.08206(19) 0.3783(2) 0.0492(8) Uani 1 1 d . . . C41 C 0.6250(2) 0.5594(2) 0.3045(2) 0.0495(8) Uani 1 1 d . . . C42 C 0.5442(2) 0.5941(2) 0.2678(2) 0.0674(10) Uani 1 1 d . . . H42 H 0.5059 0.5792 0.2135 0.081 Uiso 1 1 calc R . . C43 C 0.5183(2) 0.6513(3) 0.3102(2) 0.0724(11) Uani 1 1 d . . . H43 H 0.4631 0.6743 0.2831 0.087 Uiso 1 1 calc R . . C44 C 0.5716(2) 0.6748(2) 0.3908(2) 0.0523(9) Uani 1 1 d . A . C45 C 0.6526(2) 0.6401(2) 0.4264(2) 0.0702(11) Uani 1 1 d . . . H45 H 0.6913 0.6551 0.4805 0.084 Uiso 1 1 calc R . . C46 C 0.6788(2) 0.5834(2) 0.3841(2) 0.0703(11) Uani 1 1 d . . . H46 H 0.7343 0.5612 0.4107 0.084 Uiso 1 1 calc R . . C410 C 0.6546(3) 0.4989(2) 0.2581(3) 0.0684(11) Uani 1 1 d . . . O411 O 0.6025(2) 0.48090(15) 0.18508(17) 0.0837(8) Uani 1 1 d . . . O412 O 0.7296(2) 0.47302(18) 0.2938(2) 0.1011(10) Uani 1 1 d . . . C440 C 0.5422(2) 0.7370(2) 0.4373(2) 0.0669(10) Uani 1 1 d . . . C441 C 0.6070(7) 0.7432(8) 0.5305(6) 0.061(4) Uiso 0.397(14) 1 d P A 1 H44A H 0.6618 0.7619 0.537 0.092 Uiso 0.397(14) 1 calc PR A 1 H44B H 0.6132 0.6879 0.5559 0.092 Uiso 0.397(14) 1 calc PR A 1 H44C H 0.5863 0.7837 0.5566 0.092 Uiso 0.397(14) 1 calc PR A 1 C442 C 0.4571(7) 0.7105(8) 0.4315(8) 0.066(4) Uiso 0.397(14) 1 d P A 1 H44D H 0.4406 0.7509 0.4612 0.099 Uiso 0.397(14) 1 calc PR A 1 H44E H 0.4625 0.6545 0.4553 0.099 Uiso 0.397(14) 1 calc PR A 1 H44F H 0.414 0.7092 0.3745 0.099 Uiso 0.397(14) 1 calc PR A 1 C443 C 0.5330(8) 0.8301(6) 0.3971(7) 0.060(4) Uiso 0.397(14) 1 d P A 1 H44G H 0.5871 0.8468 0.4005 0.09 Uiso 0.397(14) 1 calc PR A 1 H44H H 0.5167 0.8708 0.4266 0.09 Uiso 0.397(14) 1 calc PR A 1 H44I H 0.4898 0.8286 0.3401 0.09 Uiso 0.397(14) 1 calc PR A 1 C444 C 0.4426(8) 0.7445(10) 0.3953(9) 0.069(5) Uiso 0.301(7) 1 d P A 2 H44J H 0.4265 0.784 0.4259 0.104 Uiso 0.301(7) 1 calc PR A 2 H44K H 0.4181 0.6892 0.3943 0.104 Uiso 0.301(7) 1 calc PR A 2 H44L H 0.4216 0.7651 0.3396 0.104 Uiso 0.301(7) 1 calc PR A 2 C445 C 0.5830(11) 0.8236(9) 0.4474(12) 0.079(5) Uiso 0.301(7) 1 d P A 2 H44M H 0.5631 0.8608 0.4766 0.119 Uiso 0.301(7) 1 calc PR A 2 H44N H 0.5676 0.8474 0.3939 0.119 Uiso 0.301(7) 1 calc PR A 2 H44O H 0.6444 0.818 0.4782 0.119 Uiso 0.301(7) 1 calc PR A 2 C446 C 0.5698(12) 0.7012(11) 0.5263(9) 0.089(5) Uiso 0.301(7) 1 d P A 2 H44P H 0.5513 0.7401 0.5555 0.134 Uiso 0.301(7) 1 calc PR A 2 H44Q H 0.6313 0.6956 0.5558 0.134 Uiso 0.301(7) 1 calc PR A 2 H44R H 0.5438 0.6461 0.5222 0.134 Uiso 0.301(7) 1 calc PR A 2 C447 C 0.4858(16) 0.8045(14) 0.3793(10) 0.112(6) Uiso 0.301(7) 1 d P A 3 H44S H 0.4674 0.8433 0.4086 0.168 Uiso 0.301(7) 1 calc PR A 3 H44T H 0.4364 0.778 0.3349 0.168 Uiso 0.301(7) 1 calc PR A 3 H44U H 0.5174 0.8356 0.357 0.168 Uiso 0.301(7) 1 calc PR A 3 C448 C 0.6158(10) 0.7825(14) 0.5077(12) 0.090(5) Uiso 0.301(7) 1 d P A 3 H44V H 0.5937 0.8204 0.5346 0.135 Uiso 0.301(7) 1 calc PR A 3 H44W H 0.6475 0.815 0.4866 0.135 Uiso 0.301(7) 1 calc PR A 3 H44Y H 0.6531 0.7409 0.5469 0.135 Uiso 0.301(7) 1 calc PR A 3 C449 C 0.4883(15) 0.6785(13) 0.4660(14) 0.120(7) Uiso 0.301(7) 1 d P A 3 H44Z H 0.4674 0.7123 0.4966 0.18 Uiso 0.301(7) 1 calc PR A 3 H441 H 0.5242 0.6332 0.5005 0.18 Uiso 0.301(7) 1 calc PR A 3 H442 H 0.4405 0.6542 0.4183 0.18 Uiso 0.301(7) 1 calc PR A 3 C51 C 0.2902(2) 0.1846(2) 0.1200(2) 0.0579(9) Uani 1 1 d . . . C52 C 0.2606(2) 0.1033(3) 0.0896(2) 0.0736(11) Uani 1 1 d . . . H52 H 0.2538 0.0876 0.0378 0.088 Uiso 1 1 calc R . . C53 C 0.2413(2) 0.0457(2) 0.1353(2) 0.0748(11) Uani 1 1 d . . . H53 H 0.222 -0.0086 0.1135 0.09 Uiso 1 1 calc R . . C54 C 0.2495(2) 0.0654(2) 0.2124(2) 0.0573(9) Uani 1 1 d . . . C55 C 0.2794(2) 0.1466(2) 0.2413(2) 0.0626(10) Uani 1 1 d . . . H55 H 0.2858 0.1628 0.2929 0.075 Uiso 1 1 calc R . . C56 C 0.3001(2) 0.2046(2) 0.1968(2) 0.0664(10) Uani 1 1 d . . . H56 H 0.3212 0.2583 0.2193 0.08 Uiso 1 1 calc R . . C510 C 0.3103(3) 0.2498(3) 0.0705(3) 0.0728(11) Uani 1 1 d . . . O511 O 0.3384(2) 0.32108(19) 0.10261(18) 0.0955(9) Uani 1 1 d . . . O512 O 0.29504(19) 0.22793(16) -0.00168(18) 0.0920(9) Uani 1 1 d . . . C540 C 0.2279(2) -0.0008(2) 0.2611(2) 0.0659(10) Uani 1 1 d . . . C541 C 0.2277(3) 0.0385(3) 0.3380(3) 0.1098(16) Uani 1 1 d . . . H54A H 0.2108 -0.0043 0.3653 0.165 Uiso 1 1 calc R . . H54B H 0.1879 0.0855 0.3216 0.165 Uiso 1 1 calc R . . H54C H 0.2844 0.0588 0.3753 0.165 Uiso 1 1 calc R . . C542 C 0.2948(3) -0.0725(3) 0.2881(3) 0.1096(16) Uani 1 1 d . . . H54D H 0.282 -0.1148 0.3189 0.164 Uiso 1 1 calc R . . H54E H 0.351 -0.049 0.3224 0.164 Uiso 1 1 calc R . . H54F H 0.2936 -0.0988 0.2401 0.164 Uiso 1 1 calc R . . C543 C 0.1385(3) -0.0394(3) 0.2073(3) 0.0963(14) Uani 1 1 d . . . H54G H 0.1256 -0.08 0.2394 0.144 Uiso 1 1 calc R . . H54H H 0.1378 -0.0678 0.1604 0.144 Uiso 1 1 calc R . . H54I H 0.0962 0.0055 0.1886 0.144 Uiso 1 1 calc R . . N61 N 0.6234(3) 0.2847(2) 0.2643(3) 0.1105(14) Uani 1 1 d . . . C62 C 0.5935(3) 0.3052(3) 0.3024(3) 0.0887(14) Uani 1 1 d . . . C63 C 0.5648(4) 0.3305(4) 0.3615(4) 0.174(3) Uani 1 1 d . . . H63A H 0.5262 0.2879 0.363 0.261 Uiso 1 1 calc R . . H63B H 0.5357 0.3847 0.3454 0.261 Uiso 1 1 calc R . . H63C H 0.6136 0.3356 0.4155 0.261 Uiso 1 1 calc R . . O71 O 0.42086(18) 0.46147(17) 0.07319(15) 0.0956(9) Uani 1 1 d . . . H71A H 0.4016 0.401 0.0815 0.143 Uiso 1 1 d R . . H71B H 0.476 0.4584 0.1194 0.143 Uiso 1 1 d R . . O72 O 0.34702(16) 0.07630(16) -0.04657(17) 0.0907(8) Uani 1 1 d . . . H72A H 0.3296 0.1263 -0.0175 0.136 Uiso 1 1 d R . . H72B H 0.3106 0.0613 -0.1007 0.136 Uiso 1 1 d R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0538(17) 0.0516(18) 0.0485(16) -0.0022(13) 0.0248(14) 0.0053(14) C2 0.043(2) 0.076(3) 0.060(2) -0.001(2) 0.0202(18) 0.0048(19) C3 0.050(2) 0.080(3) 0.062(2) -0.015(2) 0.025(2) -0.011(2) N4 0.0507(17) 0.0494(18) 0.0612(19) -0.0055(16) 0.0232(15) -0.0016(14) C5 0.053(2) 0.068(3) 0.074(3) -0.009(2) 0.032(2) -0.0073(19) C6 0.063(2) 0.059(2) 0.067(2) -0.0010(18) 0.039(2) -0.0036(18) N7 0.0669(19) 0.0444(17) 0.0627(19) -0.0056(14) 0.0375(16) 0.0021(14) C8 0.060(2) 0.054(2) 0.059(2) 0.0069(18) 0.0214(19) 0.0112(18) O11 0.0713(16) 0.0551(15) 0.0484(13) -0.0033(11) 0.0312(12) -0.0085(12) C12 0.072(2) 0.063(3) 0.049(2) -0.0060(19) 0.0240(19) -0.016(2) C13 0.060(2) 0.077(3) 0.049(2) -0.0026(19) 0.019(2) -0.020(2) O14 0.0530(14) 0.0801(17) 0.0467(14) 0.0018(12) 0.0229(12) -0.0016(13) C17 0.056(2) 0.048(2) 0.055(2) 0.0003(17) 0.0194(17) 0.0080(18) C9 0.048(2) 0.056(2) 0.045(2) 0.0037(17) 0.0183(17) 0.0072(17) C21 0.067(2) 0.062(2) 0.061(2) 0.006(2) 0.028(2) 0.0009(19) C22 0.075(3) 0.088(3) 0.051(2) 0.014(2) 0.030(2) 0.007(2) C23 0.063(2) 0.084(3) 0.047(2) -0.005(2) 0.0218(19) 0.009(2) C24 0.063(2) 0.055(2) 0.047(2) -0.0027(19) 0.0239(18) 0.0015(18) C10 0.046(2) 0.057(2) 0.0404(19) 0.0022(18) 0.0148(17) 0.0055(17) C15 0.054(2) 0.050(2) 0.047(2) 0.0010(17) 0.0271(19) -0.0060(17) C31 0.055(2) 0.079(3) 0.062(2) 0.001(2) 0.029(2) -0.0023(19) C32 0.073(3) 0.087(3) 0.080(3) 0.002(2) 0.047(3) -0.002(2) C33 0.092(3) 0.087(3) 0.069(3) 0.007(2) 0.052(3) -0.001(3) C34 0.077(3) 0.074(3) 0.052(2) 0.0026(19) 0.029(2) 0.003(2) C16 0.051(2) 0.046(2) 0.049(2) -0.0004(17) 0.0223(18) 0.0013(17) C41 0.056(2) 0.042(2) 0.056(2) -0.0011(17) 0.0308(19) -0.0011(17) C42 0.067(3) 0.076(3) 0.048(2) -0.010(2) 0.018(2) 0.005(2) C43 0.054(2) 0.087(3) 0.063(2) -0.008(2) 0.016(2) 0.023(2) C44 0.048(2) 0.053(2) 0.055(2) -0.0039(18) 0.0243(19) 0.0046(18) C45 0.053(2) 0.087(3) 0.053(2) -0.026(2) 0.0102(19) 0.009(2) C46 0.051(2) 0.074(3) 0.071(3) -0.017(2) 0.016(2) 0.012(2) C410 0.099(3) 0.045(2) 0.089(3) -0.010(2) 0.067(3) -0.015(2) O411 0.129(2) 0.0624(18) 0.0747(18) -0.0176(15) 0.0607(19) -0.0115(16) O412 0.093(2) 0.093(2) 0.137(3) -0.025(2) 0.071(2) 0.0143(19) C440 0.061(2) 0.077(3) 0.065(2) -0.007(2) 0.031(2) 0.001(2) C51 0.065(2) 0.046(2) 0.063(2) 0.013(2) 0.031(2) 0.0052(19) C52 0.104(3) 0.062(3) 0.065(2) -0.004(2) 0.048(2) -0.010(2) C53 0.107(3) 0.049(2) 0.080(3) -0.007(2) 0.054(3) -0.014(2) C54 0.063(2) 0.054(2) 0.060(2) 0.0075(19) 0.033(2) 0.0061(19) C55 0.069(3) 0.060(3) 0.055(2) 0.001(2) 0.026(2) 0.002(2) C56 0.074(3) 0.052(2) 0.072(3) 0.003(2) 0.033(2) -0.0017(19) C510 0.082(3) 0.053(3) 0.089(3) 0.016(3) 0.045(3) 0.015(2) O511 0.117(2) 0.064(2) 0.109(2) 0.0074(17) 0.0554(19) -0.0186(18) O512 0.148(3) 0.0619(17) 0.094(2) 0.0193(16) 0.080(2) 0.0154(17) C540 0.068(3) 0.061(2) 0.076(3) 0.017(2) 0.040(2) 0.003(2) C541 0.153(4) 0.112(4) 0.084(3) 0.024(3) 0.072(3) -0.010(3) C542 0.096(3) 0.080(3) 0.149(4) 0.055(3) 0.055(3) 0.016(3) C543 0.085(3) 0.101(3) 0.104(3) 0.017(3) 0.045(3) -0.019(3) N61 0.149(4) 0.080(3) 0.144(4) 0.008(2) 0.103(3) -0.003(3) C62 0.101(4) 0.065(3) 0.126(4) 0.015(3) 0.075(3) 0.008(2) C63 0.213(7) 0.167(6) 0.228(7) -0.017(5) 0.174(6) 0.019(5) O71 0.110(2) 0.0835(19) 0.0777(18) 0.0067(15) 0.0315(17) -0.0201(17) O72 0.103(2) 0.0673(18) 0.116(2) -0.0024(16) 0.0638(18) 0.0011(16) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 N1 C2 1.486(4) . ? N1 C17 1.488(4) . ? C2 C3 1.496(5) . ? C3 N4 1.454(4) . ? N4 C5 1.458(4) . ? C5 C6 1.502(4) . ? C6 N7 1.486(4) . ? N7 C8 1.500(4) . ? C8 C9 1.498(4) . ? O11 C10 1.363(3) . ? O11 C12 1.441(4) . ? C12 C13 1.489(4) . ? C13 O14 1.433(4) . ? O14 C15 1.361(3) . ? C17 C16 1.503(4) . ? C9 C21 1.375(4) . ? C9 C10 1.392(4) . ? C21 C22 1.385(5) . ? C22 C23 1.374(5) . ? C23 C24 1.375(4) . ? C24 C10 1.394(4) . ? C15 C31 1.381(4) . ? C15 C16 1.385(4) . ? C31 C32 1.380(5) . ? C32 C33 1.359(5) . ? C33 C34 1.388(5) . ? C34 C16 1.371(4) . ? C41 C46 1.364(4) . ? C41 C42 1.368(4) . ? C41 C410 1.516(5) . ? C42 C43 1.391(4) . ? C43 C44 1.374(4) . ? C44 C45 1.371(4) . ? C44 C440 1.531(4) . ? C45 C46 1.388(4) . ? C410 O412 1.234(4) . ? C410 O411 1.247(4) . ? C440 C447 1.492(17) . ? C440 C445 1.499(13) . ? C440 C448 1.508(15) . ? C440 C442 1.509(10) . ? C440 C441 1.547(10) . ? C440 C444 1.553(13) . ? C440 C446 1.567(14) . ? C440 C449 1.573(18) . ? C440 C443 1.600(11) . ? C51 C56 1.367(4) . ? C51 C52 1.383(5) . ? C51 C510 1.510(5) . ? C52 C53 1.373(5) . ? C53 C54 1.382(4) . ? C54 C55 1.378(4) . ? C54 C540 1.525(4) . ? C55 C56 1.375(4) . ? C510 O511 1.245(4) . ? C510 O512 1.265(4) . ? C540 C542 1.529(5) . ? C540 C543 1.533(5) . ? C540 C541 1.535(5) . ? N61 C62 1.100(5) . ? C62 C63 1.446(6) . ? 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 N1 C17 113.5(2) . . ? N1 C2 C3 111.1(3) . . ? N4 C3 C2 110.3(3) . . ? C3 N4 C5 111.4(3) . . ? N4 C5 C6 109.3(3) . . ? N7 C6 C5 111.0(3) . . ? C6 N7 C8 114.6(2) . . ? C9 C8 N7 112.4(3) . . ? C10 O11 C12 117.1(2) . . ? O11 C12 C13 108.9(3) . . ? O14 C13 C12 108.3(3) . . ? C15 O14 C13 117.9(2) . . ? N1 C17 C16 113.1(3) . . ? C21 C9 C10 119.0(3) . . ? C21 C9 C8 120.7(3) . . ? C10 C9 C8 120.3(3) . . ? C9 C21 C22 121.1(3) . . ? C23 C22 C21 119.2(3) . . ? C22 C23 C24 121.3(3) . . ? C23 C24 C10 119.1(3) . . ? O11 C10 C9 115.3(3) . . ? O11 C10 C24 124.4(3) . . ? C9 C10 C24 120.3(3) . . ? O14 C15 C31 124.6(3) . . ? O14 C15 C16 115.4(3) . . ? C31 C15 C16 120.0(3) . . ? C32 C31 C15 119.9(3) . . ? C33 C32 C31 120.6(4) . . ? C32 C33 C34 119.3(3) . . ? C16 C34 C33 121.2(3) . . ? C34 C16 C15 119.0(3) . . ? C34 C16 C17 120.1(3) . . ? C15 C16 C17 120.8(3) . . ? C46 C41 C42 117.2(3) . . ? C46 C41 C410 121.3(3) . . ? C42 C41 C410 121.5(4) . . ? C41 C42 C43 121.1(3) . . ? C44 C43 C42 122.1(3) . . ? C45 C44 C43 116.0(3) . . ? C45 C44 C440 122.2(3) . . ? C43 C44 C440 121.7(3) . . ? C44 C45 C46 122.0(3) . . ? C41 C46 C45 121.6(3) . . ? O412 C410 O411 124.0(4) . . ? O412 C410 C41 118.2(4) . . ? O411 C410 C41 117.8(4) . . ? C447 C440 C445 64.8(13) . . ? C447 C440 C448 107.1(10) . . ? C445 C440 C448 45.7(10) . . ? C447 C440 C442 80.6(10) . . ? C445 C440 C442 131.1(7) . . ? C448 C440 C442 128.0(9) . . ? C447 C440 C44 109.7(7) . . ? C445 C440 C44 111.8(6) . . ? C448 C440 C44 113.1(6) . . ? C442 C440 C44 111.8(5) . . ? C447 C440 C441 129.7(9) . . ? C445 C440 C441 75.2(8) . . ? C448 C440 C441 30.1(8) . . ? C442 C440 C441 106.8(7) . . ? C44 C440 C441 112.6(4) . . ? C447 C440 C444 51.4(11) . . ? C445 C440 C444 110.9(8) . . ? C448 C440 C444 134.8(8) . . ? C442 C440 C444 30.0(6) . . ? C44 C440 C444 111.8(5) . . ? C441 C440 C444 128.2(7) . . ? C447 C440 C446 140.1(9) . . ? C445 C440 C446 107.1(8) . . ? C448 C440 C446 63.7(11) . . ? C442 C440 C446 77.8(8) . . ? C44 C440 C446 109.3(6) . . ? C441 C440 C446 33.7(7) . . ? C444 C440 C446 105.6(8) . . ? C447 C440 C449 110.0(10) . . ? C445 C440 C449 144.1(9) . . ? C448 C440 C449 113.5(10) . . ? C442 C440 C449 29.6(8) . . ? C44 C440 C449 103.4(8) . . ? C441 C440 C449 85.2(9) . . ? C444 C440 C449 59.5(11) . . ? C446 C440 C449 52.3(10) . . ? C447 C440 C443 31.2(9) . . ? C445 C440 C443 34.8(7) . . ? C448 C440 C443 80.0(9) . . ? C442 C440 C443 109.5(6) . . ? C44 C440 C443 107.9(4) . . ? C441 C440 C443 108.2(6) . . ? C444 C440 C443 81.8(7) . . ? C446 C440 C443 135.6(7) . . ? C449 C440 C443 137.1(9) . . ? C56 C51 C52 117.6(3) . . ? C56 C51 C510 120.7(4) . . ? C52 C51 C510 121.7(4) . . ? C53 C52 C51 120.6(3) . . ? C52 C53 C54 122.5(3) . . ? C55 C54 C53 115.8(3) . . ? C55 C54 C540 123.5(3) . . ? C53 C54 C540 120.7(3) . . ? C56 C55 C54 122.4(3) . . ? C51 C56 C55 121.1(3) . . ? O511 C510 O512 125.1(4) . . ? O511 C510 C51 118.1(4) . . ? O512 C510 C51 116.8(4) . . ? C54 C540 C542 108.5(3) . . ? C54 C540 C543 110.7(3) . . ? C542 C540 C543 108.9(3) . . ? C54 C540 C541 112.0(3) . . ? C542 C540 C541 109.1(3) . . ? C543 C540 C541 107.5(3) . . ? N61 C62 C63 172.7(6) . . ? #===END data_lfl43 _database_code_CSD 207756 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C42 H56 N3 O9' _chemical_formula_weight 746.90 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 'P 21/c ' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 18.638(10) _cell_length_b 12.575(7) _cell_length_c 19.075(10) _cell_angle_alpha 90.00 _cell_angle_beta 113.528(9) _cell_angle_gamma 90.00 _cell_volume 4099(4) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 972 _cell_measurement_theta_min 2.383 _cell_measurement_theta_max 27.373 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.478 _exptl_crystal_size_mid 0.465 _exptl_crystal_size_min 0.237 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.210 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1604 _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_type gaussian _exptl_absorpt_correction_T_min 0.957 _exptl_absorpt_correction_T_max 0.981 _exptl_absorpt_process_details ; Gaussian (XPREP, Bruker 1995; Coppens et al., 1965) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART 1000 CCD' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 286 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0.03 _diffrn_reflns_number 35320 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0216 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.99 _diffrn_reflns_theta_max 28.25 _reflns_number_total 9213 _reflns_number_gt 6981 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker,1995)' _computing_cell_refinement 'SAINT (Bruker,1995)' _computing_data_reduction 'SAINT and XPREP (Bruker 1995)' _computing_structure_solution 'SIR97 (Altomare, et. al. 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; teXsan for Windows (MSC, 1997), XSHELL (Bruker, 2000) and WinGX (Farrugia, 1999) ; _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0400P)^2^+1.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 9213 _refine_ls_number_parameters 531 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0702 _refine_ls_R_factor_gt 0.0533 _refine_ls_wR_factor_ref 0.1299 _refine_ls_wR_factor_gt 0.1246 _refine_ls_goodness_of_fit_ref 1.301 _refine_ls_restrained_S_all 1.306 _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 0.00630(7) 0.91259(9) 0.35918(6) 0.0373(3) Uani 1 1 d . . . O2 O -0.14030(7) 0.86439(9) 0.39226(7) 0.0375(3) Uani 1 1 d . . . O3 O 0.03508(7) 0.77878(10) 0.53983(7) 0.0425(3) Uani 1 1 d . . . O4 O 0.03535(7) 0.68718(9) 0.43954(6) 0.0372(3) Uani 1 1 d . . . O5 O 0.15320(9) 0.78215(11) 0.66243(7) 0.0472(3) Uani 1 1 d . . . H5O H 0.0994(17) 0.795(2) 0.6213(17) 0.095(9) Uiso 1 1 d . . . O6 O 0.14463(9) 0.56450(10) 0.32208(8) 0.0541(4) Uani 1 1 d . A . O7 O 0.12306(9) 0.40032(11) 0.35435(8) 0.0551(4) Uani 1 1 d . A . O8A O 0.28336(13) 0.61736(16) 0.33564(12) 0.0656(5) Uiso 0.75 1 d PD A 1 H8OA H 0.2352 0.6252 0.3237 0.098 Uiso 0.75 1 calc PR A 1 O9 O 0.03031(7) 0.46896(10) 0.42852(7) 0.0468(3) Uani 1 1 d . . . H9OA H 0.0413 0.5374 0.4325 0.070 Uiso 1 1 d R . . H9OB H 0.0561 0.4477 0.4031 0.070 Uiso 1 1 d R . . N1 N -0.11521(8) 0.63417(12) 0.43415(9) 0.0385(3) Uani 1 1 d . . . H1NA H -0.0879(11) 0.6772(16) 0.4176(11) 0.039(5) Uiso 1 1 d . . . H1NB H -0.0773(13) 0.5951(17) 0.4778(13) 0.059(6) Uiso 1 1 d . . . N2 N -0.13372(10) 0.66831(13) 0.27474(9) 0.0465(4) Uani 1 1 d . . . H2NA H -0.1574(15) 0.728(2) 0.2381(16) 0.090(8) Uiso 1 1 d . . . N3 N 0.02867(9) 0.71319(11) 0.29073(8) 0.0363(3) Uani 1 1 d . . . H3NA H 0.0680(13) 0.6541(18) 0.3118(12) 0.058(6) Uiso 1 1 d . . . H3NB H 0.0087(12) 0.7303(18) 0.3253(13) 0.060(7) Uiso 1 1 d . . . C1 C -0.15490(11) 0.55535(14) 0.37170(12) 0.0468(5) Uani 1 1 d . . . H1A H -0.1967 0.5190 0.3822 0.056 Uiso 1 1 calc R . . H1B H -0.1163 0.5008 0.3723 0.056 Uiso 1 1 calc R . . C2 C -0.19037(11) 0.60472(16) 0.29282(11) 0.0500(5) Uani 1 1 d . . . H2A H -0.2112 0.5476 0.2543 0.060 Uiso 1 1 calc R . . H2B H -0.2347 0.6507 0.2894 0.060 Uiso 1 1 calc R . . C3 C -0.09305(12) 0.60597(15) 0.23700(12) 0.0502(5) Uani 1 1 d . . . H3A H -0.1319 0.5758 0.1889 0.060 Uiso 1 1 calc R . . H3B H -0.0653 0.5461 0.2705 0.060 Uiso 1 1 calc R . . C4 C -0.03501(12) 0.67245(15) 0.21925(10) 0.0461(5) Uani 1 1 d . . . H4A H -0.0117 0.6290 0.1904 0.055 Uiso 1 1 calc R . . H4B H -0.0625 0.7333 0.1866 0.055 Uiso 1 1 calc R . . C5 C 0.07194(11) 0.80535(13) 0.27640(9) 0.0369(4) Uani 1 1 d . . . H5A H 0.0337 0.8567 0.2421 0.044 Uiso 1 1 calc R . . H5B H 0.1050 0.7796 0.2502 0.044 Uiso 1 1 calc R . . C6 C 0.12273(11) 0.86100(12) 0.34895(9) 0.0346(4) Uani 1 1 d . . . C7 C 0.20347(11) 0.86495(13) 0.37308(10) 0.0399(4) Uani 1 1 d . . . H7 H 0.2273 0.8258 0.3455 0.048 Uiso 1 1 calc R . . C8 C 0.25142(11) 0.92504(14) 0.43708(10) 0.0426(4) Uani 1 1 d . B . C9 C 0.21330(12) 0.97889(15) 0.47627(11) 0.0467(5) Uani 1 1 d . . . H9 H 0.2437 1.0195 0.5201 0.056 Uiso 1 1 calc R . . C10 C 0.13236(12) 0.97561(14) 0.45375(10) 0.0431(4) Uani 1 1 d . . . H10 H 0.1086 1.0129 0.4822 0.052 Uiso 1 1 calc R . . C11 C 0.08686(11) 0.91767(12) 0.38960(9) 0.0358(4) Uani 1 1 d . . . C12 C -0.03274(12) 0.97027(14) 0.39920(11) 0.0418(4) Uani 1 1 d . . . H12A H -0.0197 1.0468 0.4010 0.050 Uiso 1 1 calc R . . H12B H -0.0147 0.9439 0.4524 0.050 Uiso 1 1 calc R . . C13 C -0.11948(11) 0.95561(14) 0.35906(11) 0.0417(4) Uani 1 1 d . . . H13A H -0.1472 1.0195 0.3657 0.050 Uiso 1 1 calc R . . H13B H -0.1342 0.9442 0.3037 0.050 Uiso 1 1 calc R . . C14 C -0.21827(10) 0.83803(13) 0.36768(9) 0.0348(4) Uani 1 1 d . . . C15 C -0.27957(12) 0.88938(16) 0.30978(10) 0.0462(5) Uani 1 1 d . . . H15 H -0.2702 0.9507 0.2856 0.055 Uiso 1 1 calc R . . C16 C -0.35488(12) 0.84925(18) 0.28797(11) 0.0528(5) Uani 1 1 d . . . H16 H -0.3964 0.8842 0.2480 0.063 Uiso 1 1 calc R . . C17 C -0.37272(11) 0.76040(17) 0.32168(11) 0.0469(5) Uani 1 1 d . . . C18 C -0.31002(10) 0.71319(15) 0.38160(10) 0.0410(4) Uani 1 1 d . . . H18 H -0.3199 0.6540 0.4074 0.049 Uiso 1 1 calc R . . C19 C -0.23359(10) 0.75027(14) 0.40465(9) 0.0359(4) Uani 1 1 d . . . C20 C -0.16622(10) 0.69317(15) 0.46520(10) 0.0389(4) Uani 1 1 d . . . H20A H -0.1338 0.7457 0.5034 0.047 Uiso 1 1 calc R . . H20B H -0.1872 0.6421 0.4918 0.047 Uiso 1 1 calc R . . C21 C 0.34018(12) 0.93186(17) 0.45980(12) 0.0516(5) Uani 1 1 d . . . C22A C 0.37780(16) 0.8196(2) 0.47689(18) 0.0742(8) Uani 0.90 1 d P B 1 H22A H 0.4344 0.8257 0.4920 0.111 Uiso 0.90 1 calc PR B 1 H22B H 0.3553 0.7753 0.4310 0.111 Uiso 0.90 1 calc PR B 1 H22C H 0.3674 0.7869 0.5185 0.111 Uiso 0.90 1 calc PR B 1 C23A C 0.35749(15) 0.9805(3) 0.39393(16) 0.0721(8) Uani 0.90 1 d P B 1 H23A H 0.3355 1.0523 0.3830 0.108 Uiso 0.90 1 calc PR B 1 H23B H 0.3338 0.9361 0.3482 0.108 Uiso 0.90 1 calc PR B 1 H23C H 0.4142 0.9838 0.4088 0.108 Uiso 0.90 1 calc PR B 1 C24A C 0.38202(16) 0.9999(3) 0.53209(17) 0.0788(9) Uani 0.90 1 d P B 1 H24A H 0.3741 0.9680 0.5753 0.118 Uiso 0.90 1 calc PR B 1 H24B H 0.3604 1.0721 0.5233 0.118 Uiso 0.90 1 calc PR B 1 H24C H 0.4381 1.0028 0.5436 0.118 Uiso 0.90 1 calc PR B 1 C25 C -0.45676(11) 0.7167(2) 0.29421(13) 0.0605(6) Uani 1 1 d . . . C26 C -0.50566(13) 0.7910(3) 0.32174(15) 0.0802(8) Uani 1 1 d . . . H26A H -0.4829 0.7933 0.3777 0.120 Uiso 1 1 calc R . . H26B H -0.5595 0.7643 0.3035 0.120 Uiso 1 1 calc R . . H26C H -0.5058 0.8627 0.3015 0.120 Uiso 1 1 calc R . . C27 C -0.45831(14) 0.6043(3) 0.3255(2) 0.1005(11) Uani 1 1 d . . . H27A H -0.4260 0.5565 0.3096 0.151 Uiso 1 1 calc R . . H27B H -0.5123 0.5780 0.3054 0.151 Uiso 1 1 calc R . . H27C H -0.4376 0.6067 0.3815 0.151 Uiso 1 1 calc R . . C28 C -0.49346(14) 0.7116(3) 0.20639(15) 0.0908(10) Uani 1 1 d . . . H28A H -0.4955 0.7833 0.1855 0.136 Uiso 1 1 calc R . . H28B H -0.5466 0.6828 0.1891 0.136 Uiso 1 1 calc R . . H28C H -0.4617 0.6656 0.1887 0.136 Uiso 1 1 calc R . . C29 C 0.15519(9) 0.70068(12) 0.54929(9) 0.0303(3) Uani 1 1 d . . . C30 C 0.19264(10) 0.72926(13) 0.62678(9) 0.0348(4) Uani 1 1 d . . . C31 C 0.27109(11) 0.70223(16) 0.66791(11) 0.0456(5) Uani 1 1 d . . . H31 H 0.2964 0.7212 0.7203 0.055 Uiso 1 1 calc R . . C32 C 0.31195(11) 0.64791(17) 0.63250(12) 0.0512(5) Uani 1 1 d . . . H32 H 0.3650 0.6290 0.6611 0.061 Uiso 1 1 calc R . . C33 C 0.27641(11) 0.62071(16) 0.55585(12) 0.0476(5) Uani 1 1 d . . . H33 H 0.3050 0.5842 0.5317 0.057 Uiso 1 1 calc R . . C34 C 0.19844(10) 0.64754(14) 0.51477(10) 0.0376(4) Uani 1 1 d . . . H34 H 0.1740 0.6294 0.4621 0.045 Uiso 1 1 calc R . . C35 C 0.06953(9) 0.72406(12) 0.50622(9) 0.0313(3) Uani 1 1 d . . . C36 C 0.25316(12) 0.44804(16) 0.37434(10) 0.0456(5) Uani 1 1 d . A . C37 C 0.30631(14) 0.52442(17) 0.37077(12) 0.0617(6) Uani 1 1 d D . . C38 C 0.38611(17) 0.5035(3) 0.39904(16) 0.0847(9) Uani 1 1 d . A . H38 H 0.4212 0.5571 0.3971 0.102 Uiso 1 1 calc R . . C39 C 0.41427(18) 0.4067(3) 0.42941(17) 0.0916(10) Uani 1 1 d . . . H39 H 0.4689 0.3928 0.4486 0.110 Uiso 1 1 calc R A . C40 C 0.36331(18) 0.3284(3) 0.43225(15) 0.0854(9) Uani 1 1 d . A . H40 H 0.3828 0.2604 0.4527 0.103 Uiso 1 1 calc R . . C41 C 0.28355(14) 0.34941(19) 0.40512(12) 0.0625(6) Uani 1 1 d D . . C42 C 0.16718(12) 0.47193(15) 0.34803(10) 0.0428(4) Uani 1 1 d . . . O8B O 0.2369(3) 0.2674(4) 0.3996(4) 0.0593(15) Uiso 0.25 1 d PD A 2 H8OB H 0.1928 0.2896 0.3950 0.089 Uiso 0.25 1 calc PR A 2 C22B C 0.3643(14) 0.875(2) 0.4082(14) 0.062(6) Uiso 0.10 1 d P B 2 H22D H 0.3367 0.9032 0.3563 0.093 Uiso 0.10 1 calc PR B 2 H22E H 0.3520 0.7995 0.4090 0.093 Uiso 0.10 1 calc PR B 2 H22F H 0.4209 0.8838 0.4237 0.093 Uiso 0.10 1 calc PR B 2 C23B C 0.3533(12) 1.0573(16) 0.4512(12) 0.048(5) Uiso 0.10 1 d P B 2 H23D H 0.3369 1.0976 0.4862 0.072 Uiso 0.10 1 calc PR B 2 H23E H 0.3222 1.0797 0.3985 0.072 Uiso 0.10 1 calc PR B 2 H23F H 0.4089 1.0708 0.4636 0.072 Uiso 0.10 1 calc PR B 2 C24B C 0.3738(15) 0.903(2) 0.5424(14) 0.067(6) Uiso 0.10 1 d P B 2 H24D H 0.3512 0.9483 0.5699 0.100 Uiso 0.10 1 calc PR B 2 H24E H 0.4307 0.9125 0.5635 0.100 Uiso 0.10 1 calc PR B 2 H24F H 0.3617 0.8282 0.5480 0.100 Uiso 0.10 1 calc PR B 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0524(8) 0.0313(6) 0.0348(6) -0.0042(5) 0.0244(6) -0.0017(5) O2 0.0440(7) 0.0332(6) 0.0355(6) 0.0068(5) 0.0162(5) -0.0006(5) O3 0.0438(7) 0.0412(7) 0.0461(7) 0.0041(6) 0.0217(6) 0.0067(6) O4 0.0370(6) 0.0355(6) 0.0323(6) 0.0057(5) 0.0066(5) -0.0033(5) O5 0.0593(9) 0.0514(8) 0.0348(7) -0.0031(6) 0.0229(7) 0.0007(7) O6 0.0703(9) 0.0378(7) 0.0492(8) 0.0032(6) 0.0188(7) 0.0111(7) O7 0.0603(9) 0.0456(8) 0.0500(8) -0.0006(6) 0.0123(7) -0.0057(7) O9 0.0406(7) 0.0365(7) 0.0510(8) 0.0095(6) 0.0053(6) 0.0002(5) N1 0.0286(7) 0.0361(8) 0.0437(9) 0.0133(7) 0.0068(7) -0.0024(6) N2 0.0531(10) 0.0360(8) 0.0400(9) -0.0057(7) 0.0077(7) 0.0067(7) N3 0.0483(9) 0.0280(7) 0.0289(7) -0.0032(6) 0.0116(7) 0.0001(7) C1 0.0336(9) 0.0325(9) 0.0657(13) 0.0005(9) 0.0107(9) -0.0025(8) C2 0.0392(10) 0.0455(11) 0.0519(11) -0.0139(9) 0.0043(9) -0.0017(8) C3 0.0513(11) 0.0391(10) 0.0477(11) -0.0155(9) 0.0065(9) 0.0009(9) C4 0.0588(12) 0.0401(10) 0.0306(9) -0.0098(8) 0.0087(8) 0.0016(9) C5 0.0513(10) 0.0327(9) 0.0297(8) -0.0013(7) 0.0193(8) 0.0026(8) C6 0.0519(10) 0.0240(8) 0.0311(8) 0.0006(6) 0.0199(8) -0.0017(7) C7 0.0559(11) 0.0302(9) 0.0374(9) -0.0007(7) 0.0224(8) 0.0011(8) C8 0.0532(11) 0.0348(9) 0.0394(10) -0.0001(8) 0.0182(9) -0.0072(8) C9 0.0653(13) 0.0407(10) 0.0364(10) -0.0101(8) 0.0227(9) -0.0182(9) C10 0.0645(13) 0.0354(9) 0.0398(10) -0.0104(8) 0.0316(9) -0.0136(9) C11 0.0563(11) 0.0249(8) 0.0332(9) 0.0005(7) 0.0251(8) -0.0061(7) C12 0.0663(13) 0.0288(9) 0.0454(10) -0.0053(7) 0.0382(10) -0.0066(8) C13 0.0613(12) 0.0312(9) 0.0431(10) 0.0070(8) 0.0319(9) 0.0037(8) C14 0.0386(9) 0.0354(9) 0.0299(8) 0.0006(7) 0.0130(7) 0.0054(7) C15 0.0549(12) 0.0449(11) 0.0393(10) 0.0132(8) 0.0193(9) 0.0179(9) C16 0.0442(11) 0.0655(13) 0.0412(10) 0.0102(10) 0.0091(9) 0.0244(10) C17 0.0348(10) 0.0571(12) 0.0433(10) -0.0026(9) 0.0097(8) 0.0108(9) C18 0.0342(9) 0.0432(10) 0.0432(10) 0.0035(8) 0.0128(8) 0.0039(8) C19 0.0347(9) 0.0377(9) 0.0323(9) 0.0051(7) 0.0102(7) 0.0046(7) C20 0.0324(9) 0.0443(10) 0.0366(9) 0.0132(8) 0.0101(7) -0.0001(7) C21 0.0514(12) 0.0505(12) 0.0485(11) -0.0032(9) 0.0154(9) -0.0087(9) C22A 0.0574(16) 0.0690(18) 0.085(2) 0.0038(15) 0.0167(14) 0.0029(14) C23A 0.0524(15) 0.092(2) 0.0700(17) 0.0081(15) 0.0228(13) -0.0168(14) C24A 0.0582(16) 0.094(2) 0.0703(18) -0.0229(16) 0.0112(14) -0.0187(15) C25 0.0322(10) 0.0797(16) 0.0581(13) -0.0102(12) 0.0059(9) 0.0083(10) C26 0.0378(12) 0.124(2) 0.0712(16) -0.0282(16) 0.0142(11) 0.0084(13) C27 0.0389(13) 0.098(2) 0.142(3) 0.006(2) 0.0129(15) -0.0172(14) C28 0.0479(13) 0.146(3) 0.0637(16) -0.0366(17) 0.0062(12) 0.0019(16) C29 0.0336(8) 0.0265(8) 0.0309(8) 0.0025(6) 0.0131(7) -0.0057(6) C30 0.0398(9) 0.0314(8) 0.0333(9) 0.0009(7) 0.0149(7) -0.0062(7) C31 0.0418(10) 0.0498(11) 0.0351(9) -0.0027(8) 0.0049(8) -0.0119(9) C32 0.0299(9) 0.0568(12) 0.0563(12) 0.0015(10) 0.0061(9) -0.0037(9) C33 0.0369(10) 0.0538(12) 0.0541(12) -0.0026(9) 0.0204(9) 0.0037(9) C34 0.0382(9) 0.0386(9) 0.0349(9) -0.0030(7) 0.0133(7) -0.0023(7) C35 0.0353(9) 0.0257(8) 0.0333(9) 0.0081(7) 0.0140(7) -0.0029(7) C36 0.0583(12) 0.0455(11) 0.0303(9) -0.0066(8) 0.0146(8) 0.0052(9) C37 0.0650(15) 0.0714(15) 0.0492(12) -0.0060(11) 0.0232(11) -0.0029(12) C38 0.0653(17) 0.121(3) 0.0705(17) -0.0148(18) 0.0294(14) -0.0176(17) C39 0.0639(17) 0.130(3) 0.0750(19) -0.017(2) 0.0215(15) 0.0178(19) C40 0.086(2) 0.089(2) 0.0660(17) -0.0041(15) 0.0144(15) 0.0377(17) C41 0.0701(15) 0.0631(14) 0.0440(11) -0.0031(10) 0.0118(11) 0.0200(12) C42 0.0584(12) 0.0378(10) 0.0270(8) -0.0054(7) 0.0115(8) 0.0028(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C11 1.378(2) . ? O1 C12 1.443(2) . ? O2 C14 1.377(2) . ? O2 C13 1.437(2) . ? O3 C35 1.275(2) . ? O4 C35 1.262(2) . ? O5 C30 1.358(2) . ? O5 H5O 1.01(3) . ? O6 C42 1.269(2) . ? O7 C42 1.257(2) . ? O8A C37 1.3301(18) . ? O8A H8OA 0.8400 . ? O9 H9OA 0.8810 . ? O9 H9OB 0.8500 . ? N1 C1 1.499(2) . ? N1 C20 1.502(2) . ? N1 H1NA 0.88(2) . ? N1 H1NB 0.98(2) . ? N2 C3 1.464(3) . ? N2 C2 1.471(3) . ? N2 H2NA 1.00(3) . ? N3 C4 1.496(2) . ? N3 C5 1.498(2) . ? N3 H3NA 1.01(2) . ? N3 H3NB 0.90(2) . ? C1 C2 1.514(3) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.509(3) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.502(2) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.388(3) . ? C6 C11 1.403(2) . ? C7 C8 1.410(3) . ? C7 H7 0.9500 . ? C8 C9 1.395(3) . ? C8 C21 1.536(3) . ? C9 C10 1.395(3) . ? C9 H9 0.9500 . ? C10 C11 1.385(2) . ? C10 H10 0.9500 . ? C12 C13 1.499(3) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C15 1.391(2) . ? C14 C19 1.399(2) . ? C15 C16 1.390(3) . ? C15 H15 0.9500 . ? C16 C17 1.394(3) . ? C16 H16 0.9500 . ? C17 C18 1.399(3) . ? C17 C25 1.541(3) . ? C18 C19 1.393(3) . ? C18 H18 0.9500 . ? C19 C20 1.506(2) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C21 C22B 1.43(2) . ? C21 C24B 1.49(2) . ? C21 C23A 1.543(3) . ? C21 C24A 1.544(3) . ? C21 C22A 1.552(3) . ? C21 C23B 1.62(2) . ? C22A H22A 0.9800 . ? C22A H22B 0.9800 . ? C22A H22C 0.9800 . ? C23A H23A 0.9800 . ? C23A H23B 0.9800 . ? C23A H23C 0.9800 . ? C24A H24A 0.9800 . ? C24A H24B 0.9800 . ? C24A H24C 0.9800 . ? C25 C26 1.536(3) . ? C25 C28 1.537(3) . ? C25 C27 1.540(4) . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 H28C 0.9800 . ? C29 C34 1.398(2) . ? C29 C30 1.406(2) . ? C29 C35 1.504(2) . ? C30 C31 1.398(3) . ? C31 C32 1.383(3) . ? C31 H31 0.9500 . ? C32 C33 1.386(3) . ? C32 H32 0.9500 . ? C33 C34 1.389(3) . ? C33 H33 0.9500 . ? C34 H34 0.9500 . ? C36 C41 1.392(3) . ? C36 C37 1.401(3) . ? C36 C42 1.506(3) . ? C37 C38 1.390(4) . ? C38 C39 1.360(5) . ? C38 H38 0.9500 . ? C39 C40 1.384(5) . ? C39 H39 0.9500 . ? C40 C41 1.390(4) . ? C40 H40 0.9500 . ? C41 O8B 1.325(2) . ? O8B H8OB 0.8400 . ? C22B H22D 0.9800 . ? C22B H22E 0.9800 . ? C22B H22F 0.9800 . ? C23B H23D 0.9800 . ? C23B H23E 0.9800 . ? C23B H23F 0.9800 . ? C24B H24D 0.9800 . ? C24B H24E 0.9800 . ? C24B H24F 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C11 O1 C12 116.66(13) . . ? C14 O2 C13 118.42(13) . . ? C30 O5 H5O 104.9(16) . . ? C37 O8A H8OA 109.5 . . ? H9OA O9 H9OB 101.1 . . ? C1 N1 C20 116.81(14) . . ? C1 N1 H1NA 107.1(12) . . ? C20 N1 H1NA 112.6(12) . . ? C1 N1 H1NB 107.7(13) . . ? C20 N1 H1NB 105.5(12) . . ? H1NA N1 H1NB 106.7(17) . . ? C3 N2 C2 112.66(16) . . ? C3 N2 H2NA 103.1(15) . . ? C2 N2 H2NA 114.4(15) . . ? C4 N3 C5 112.81(14) . . ? C4 N3 H3NA 107.3(12) . . ? C5 N3 H3NA 106.6(12) . . ? C4 N3 H3NB 109.8(14) . . ? C5 N3 H3NB 110.9(14) . . ? H3NA N3 H3NB 109.3(19) . . ? N1 C1 C2 113.57(15) . . ? N1 C1 H1A 108.9 . . ? C2 C1 H1A 108.9 . . ? N1 C1 H1B 108.9 . . ? C2 C1 H1B 108.9 . . ? H1A C1 H1B 107.7 . . ? N2 C2 C1 112.73(16) . . ? N2 C2 H2A 109.0 . . ? C1 C2 H2A 109.0 . . ? N2 C2 H2B 109.0 . . ? C1 C2 H2B 109.0 . . ? H2A C2 H2B 107.8 . . ? N2 C3 C4 111.84(16) . . ? N2 C3 H3A 109.2 . . ? C4 C3 H3A 109.2 . . ? N2 C3 H3B 109.2 . . ? C4 C3 H3B 109.2 . . ? H3A C3 H3B 107.9 . . ? N3 C4 C3 111.36(15) . . ? N3 C4 H4A 109.4 . . ? C3 C4 H4A 109.4 . . ? N3 C4 H4B 109.4 . . ? C3 C4 H4B 109.4 . . ? H4A C4 H4B 108.0 . . ? N3 C5 C6 112.31(13) . . ? N3 C5 H5A 109.1 . . ? C6 C5 H5A 109.1 . . ? N3 C5 H5B 109.1 . . ? C6 C5 H5B 109.1 . . ? H5A C5 H5B 107.9 . . ? C7 C6 C11 119.42(16) . . ? C7 C6 C5 121.56(15) . . ? C11 C6 C5 118.80(16) . . ? C6 C7 C8 122.33(17) . . ? C6 C7 H7 118.8 . . ? C8 C7 H7 118.8 . . ? C9 C8 C7 116.21(18) . . ? C9 C8 C21 122.90(17) . . ? C7 C8 C21 120.86(17) . . ? C10 C9 C8 122.71(17) . . ? C10 C9 H9 118.6 . . ? C8 C9 H9 118.6 . . ? C11 C10 C9 119.54(17) . . ? C11 C10 H10 120.2 . . ? C9 C10 H10 120.2 . . ? O1 C11 C10 125.17(16) . . ? O1 C11 C6 115.02(15) . . ? C10 C11 C6 119.77(18) . . ? O1 C12 C13 109.68(15) . . ? O1 C12 H12A 109.7 . . ? C13 C12 H12A 109.7 . . ? O1 C12 H12B 109.7 . . ? C13 C12 H12B 109.7 . . ? H12A C12 H12B 108.2 . . ? O2 C13 C12 107.40(14) . . ? O2 C13 H13A 110.2 . . ? C12 C13 H13A 110.2 . . ? O2 C13 H13B 110.2 . . ? C12 C13 H13B 110.2 . . ? H13A C13 H13B 108.5 . . ? O2 C14 C15 125.40(16) . . ? O2 C14 C19 114.71(14) . . ? C15 C14 C19 119.87(17) . . ? C16 C15 C14 118.72(18) . . ? C16 C15 H15 120.6 . . ? C14 C15 H15 120.6 . . ? C15 C16 C17 123.46(17) . . ? C15 C16 H16 118.3 . . ? C17 C16 H16 118.3 . . ? C16 C17 C18 116.20(18) . . ? C16 C17 C25 121.75(18) . . ? C18 C17 C25 122.1(2) . . ? C19 C18 C17 122.09(18) . . ? C19 C18 H18 119.0 . . ? C17 C18 H18 119.0 . . ? C18 C19 C14 119.59(15) . . ? C18 C19 C20 121.13(16) . . ? C14 C19 C20 119.15(15) . . ? N1 C20 C19 113.47(15) . . ? N1 C20 H20A 108.9 . . ? C19 C20 H20A 108.9 . . ? N1 C20 H20B 108.9 . . ? C19 C20 H20B 108.9 . . ? H20A C20 H20B 107.7 . . ? C22B C21 C24B 119.4(14) . . ? C22B C21 C8 112.2(10) . . ? C24B C21 C8 103.7(10) . . ? C22B C21 C23A 53.8(10) . . ? C24B C21 C23A 145.3(10) . . ? C8 C21 C23A 110.13(18) . . ? C22B C21 C24A 135.0(10) . . ? C24B C21 C24A 48.9(10) . . ? C8 C21 C24A 112.71(19) . . ? C23A C21 C24A 108.2(2) . . ? C22B C21 C22A 56.6(10) . . ? C24B C21 C22A 65.8(10) . . ? C8 C21 C22A 110.72(18) . . ? C23A C21 C22A 107.9(2) . . ? C24A C21 C22A 107.0(2) . . ? C22B C21 C23B 108.4(12) . . ? C24B C21 C23B 109.3(13) . . ? C8 C21 C23B 102.5(7) . . ? C23A C21 C23B 56.0(7) . . ? C24A C21 C23B 60.4(7) . . ? C22A C21 C23B 146.7(7) . . ? C21 C22A H22A 109.5 . . ? C21 C22A H22B 109.5 . . ? C21 C22A H22C 109.5 . . ? C21 C23A H23A 109.5 . . ? C21 C23A H23B 109.5 . . ? C21 C23A H23C 109.5 . . ? C21 C24A H24A 109.5 . . ? C21 C24A H24B 109.5 . . ? C21 C24A H24C 109.5 . . ? C26 C25 C28 109.3(2) . . ? C26 C25 C27 108.7(2) . . ? C28 C25 C27 108.4(2) . . ? C26 C25 C17 109.17(19) . . ? C28 C25 C17 109.6(2) . . ? C27 C25 C17 111.68(18) . . ? C25 C26 H26A 109.5 . . ? C25 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C25 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C25 C27 H27A 109.5 . . ? C25 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C25 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C25 C28 H28A 109.5 . . ? C25 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C25 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C34 C29 C30 118.67(15) . . ? C34 C29 C35 121.47(15) . . ? C30 C29 C35 119.83(15) . . ? O5 C30 C31 119.49(16) . . ? O5 C30 C29 120.72(16) . . ? C31 C30 C29 119.80(16) . . ? C32 C31 C30 120.17(17) . . ? C32 C31 H31 119.9 . . ? C30 C31 H31 119.9 . . ? C31 C32 C33 120.84(18) . . ? C31 C32 H32 119.6 . . ? C33 C32 H32 119.6 . . ? C32 C33 C34 119.13(18) . . ? C32 C33 H33 120.4 . . ? C34 C33 H33 120.4 . . ? C33 C34 C29 121.37(17) . . ? C33 C34 H34 119.3 . . ? C29 C34 H34 119.3 . . ? O4 C35 O3 123.54(16) . . ? O4 C35 C29 118.52(15) . . ? O3 C35 C29 117.94(15) . . ? C41 C36 C37 117.1(2) . . ? C41 C36 C42 121.2(2) . . ? C37 C36 C42 121.74(18) . . ? O8A C37 C38 116.2(2) . . ? O8A C37 C36 122.4(2) . . ? C38 C37 C36 121.3(2) . . ? C39 C38 C37 120.4(3) . . ? C39 C38 H38 119.8 . . ? C37 C38 H38 119.8 . . ? C38 C39 C40 119.9(3) . . ? C38 C39 H39 120.0 . . ? C40 C39 H39 120.0 . . ? C39 C40 C41 119.9(3) . . ? C39 C40 H40 120.0 . . ? C41 C40 H40 120.0 . . ? O8B C41 C40 116.8(3) . . ? O8B C41 C36 121.1(3) . . ? C40 C41 C36 121.4(3) . . ? O7 C42 O6 124.53(19) . . ? O7 C42 C36 118.35(17) . . ? O6 C42 C36 117.11(18) . . ? C41 O8B H8OB 109.5 . . ? C21 C22B H22D 109.5 . . ? C21 C22B H22E 109.5 . . ? H22D C22B H22E 109.5 . . ? C21 C22B H22F 109.5 . . ? H22D C22B H22F 109.5 . . ? H22E C22B H22F 109.5 . . ? C21 C23B H23D 109.5 . . ? C21 C23B H23E 109.5 . . ? H23D C23B H23E 109.5 . . ? C21 C23B H23F 109.5 . . ? H23D C23B H23F 109.5 . . ? H23E C23B H23F 109.5 . . ? C21 C24B H24D 109.5 . . ? C21 C24B H24E 109.5 . . ? H24D C24B H24E 109.5 . . ? C21 C24B H24F 109.5 . . ? H24D C24B H24F 109.5 . . ? H24E C24B H24F 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 C20 N1 C1 C2 84.0(2) . . . . ? C3 N2 C2 C1 90.93(19) . . . . ? N1 C1 C2 N2 53.7(2) . . . . ? C2 N2 C3 C4 -179.76(15) . . . . ? C5 N3 C4 C3 -161.66(15) . . . . ? N2 C3 C4 N3 63.3(2) . . . . ? C4 N3 C5 C6 167.08(15) . . . . ? N3 C5 C6 C7 117.17(18) . . . . ? N3 C5 C6 C11 -68.24(19) . . . . ? C11 C6 C7 C8 -0.6(2) . . . . ? C5 C6 C7 C8 173.96(16) . . . . ? C6 C7 C8 C9 1.4(3) . . . . ? C6 C7 C8 C21 -177.02(17) . . . . ? C7 C8 C9 C10 -0.8(3) . . . . ? C21 C8 C9 C10 177.57(18) . . . . ? C8 C9 C10 C11 -0.6(3) . . . . ? C12 O1 C11 C10 -1.8(2) . . . . ? C12 O1 C11 C6 -179.74(13) . . . . ? C9 C10 C11 O1 -176.43(16) . . . . ? C9 C10 C11 C6 1.4(3) . . . . ? C7 C6 C11 O1 177.21(14) . . . . ? C5 C6 C11 O1 2.5(2) . . . . ? C7 C6 C11 C10 -0.9(2) . . . . ? C5 C6 C11 C10 -175.57(15) . . . . ? C11 O1 C12 C13 -179.56(13) . . . . ? C14 O2 C13 C12 176.37(13) . . . . ? O1 C12 C13 O2 90.84(16) . . . . ? C13 O2 C14 C15 3.5(2) . . . . ? C13 O2 C14 C19 -178.05(14) . . . . ? O2 C14 C15 C16 175.90(17) . . . . ? C19 C14 C15 C16 -2.4(3) . . . . ? C14 C15 C16 C17 0.7(3) . . . . ? C15 C16 C17 C18 1.6(3) . . . . ? C15 C16 C17 C25 -178.28(19) . . . . ? C16 C17 C18 C19 -2.2(3) . . . . ? C25 C17 C18 C19 177.64(18) . . . . ? C17 C18 C19 C14 0.6(3) . . . . ? C17 C18 C19 C20 -175.29(17) . . . . ? O2 C14 C19 C18 -176.69(15) . . . . ? C15 C14 C19 C18 1.8(3) . . . . ? O2 C14 C19 C20 -0.7(2) . . . . ? C15 C14 C19 C20 177.77(16) . . . . ? C1 N1 C20 C19 -55.0(2) . . . . ? C18 C19 C20 N1 107.26(19) . . . . ? C14 C19 C20 N1 -68.6(2) . . . . ? C9 C8 C21 C22B -176.3(11) . . . . ? C7 C8 C21 C22B 2.0(11) . . . . ? C9 C8 C21 C24B 53.5(11) . . . . ? C7 C8 C21 C24B -128.2(11) . . . . ? C9 C8 C21 C23A -118.3(2) . . . . ? C7 C8 C21 C23A 60.0(3) . . . . ? C9 C8 C21 C24A 2.6(3) . . . . ? C7 C8 C21 C24A -179.1(2) . . . . ? C9 C8 C21 C22A 122.4(2) . . . . ? C7 C8 C21 C22A -59.3(3) . . . . ? C9 C8 C21 C23B -60.3(8) . . . . ? C7 C8 C21 C23B 118.0(8) . . . . ? C16 C17 C25 C26 -74.2(3) . . . . ? C18 C17 C25 C26 106.0(2) . . . . ? C16 C17 C25 C28 45.5(3) . . . . ? C18 C17 C25 C28 -134.3(2) . . . . ? C16 C17 C25 C27 165.6(2) . . . . ? C18 C17 C25 C27 -14.2(3) . . . . ? C34 C29 C30 O5 179.17(15) . . . . ? C35 C29 C30 O5 -3.0(2) . . . . ? C34 C29 C30 C31 -1.4(2) . . . . ? C35 C29 C30 C31 176.43(15) . . . . ? O5 C30 C31 C32 179.70(17) . . . . ? C29 C30 C31 C32 0.3(3) . . . . ? C30 C31 C32 C33 0.9(3) . . . . ? C31 C32 C33 C34 -0.8(3) . . . . ? C32 C33 C34 C29 -0.4(3) . . . . ? C30 C29 C34 C33 1.5(2) . . . . ? C35 C29 C34 C33 -176.32(16) . . . . ? C34 C29 C35 O4 5.6(2) . . . . ? C30 C29 C35 O4 -172.16(14) . . . . ? C34 C29 C35 O3 -175.57(15) . . . . ? C30 C29 C35 O3 6.7(2) . . . . ? C41 C36 C37 O8A 173.0(2) . . . . ? C42 C36 C37 O8A -8.5(3) . . . . ? C41 C36 C37 C38 -2.0(3) . . . . ? C42 C36 C37 C38 176.4(2) . . . . ? O8A C37 C38 C39 -173.8(3) . . . . ? C36 C37 C38 C39 1.5(4) . . . . ? C37 C38 C39 C40 0.0(4) . . . . ? C38 C39 C40 C41 -1.0(4) . . . . ? C39 C40 C41 O8B 170.9(4) . . . . ? C39 C40 C41 C36 0.4(4) . . . . ? C37 C36 C41 O8B -169.0(4) . . . . ? C42 C36 C41 O8B 12.5(4) . . . . ? C37 C36 C41 C40 1.0(3) . . . . ? C42 C36 C41 C40 -177.4(2) . . . . ? C41 C36 C42 O7 -0.2(3) . . . . ? C37 C36 C42 O7 -178.55(17) . . . . ? C41 C36 C42 O6 178.64(18) . . . . ? C37 C36 C42 O6 0.2(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 O5 H5O O3 1.01(3) 1.55(3) 2.491(2) 153(3) . O8A H8OA O6 0.84 1.84 2.581(3) 146.1 . O8B H8OB O7 0.84 1.85 2.565(6) 142.1 . O9 H9OA O4 0.88 1.89 2.751(2) 163.6 . O9 H9OB O7 0.85 1.93 2.773(2) 174.7 . N1 H1NA O4 0.88(2) 2.169(19) 2.846(2) 133.2(16) . N1 H1NA O2 0.88(2) 2.520(19) 2.990(2) 114.0(14) . N1 H1NB O9 0.98(2) 1.83(2) 2.782(2) 161.6(18) 3_566 N2 H2NA O8B 1.00(3) 2.50(3) 3.347(6) 143(2) 2 N3 H3NA O6 1.01(2) 1.77(2) 2.737(2) 160.2(19) . N3 H3NB O4 0.90(2) 2.10(2) 2.810(2) 134.4(19) . N3 H3NB O1 0.90(2) 2.39(2) 2.933(2) 119.0(17) . N3 H3NB N2 0.90(2) 2.56(2) 2.972(3) 108.6(16) . _diffrn_measured_fraction_theta_max 0.908 _diffrn_reflns_theta_full 28.25 _diffrn_measured_fraction_theta_full 0.908 _refine_diff_density_max 0.522 _refine_diff_density_min -0.289 _refine_diff_density_rms 0.038