# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Prof Isabel Santos ' _publ_contact_author_email ISANTOS@ITN.PT _publ_section_title ; Tris(pyrazolyl)methane 99mTc tricarbonyl complexes for myocardial imaging ; loop_ _publ_author_name 'Isabel Santos' 'Celia Fernandes' 'Lurdes Gano' 'Raquel Garcia' 'Leonor Maria' 'Antonio Paulo' ; I.C.Santos ; # Attachment 'Compound_2.cif' data_compound2 _database_code_depnum_ccdc_archive 'CCDC 697208' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C56 H92 N12 Na O18, C4 H8 O, I' _chemical_formula_sum 'C60 H100 I N12 Na O19' _chemical_formula_weight 1443.41 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' Na Na 0.0362 0.0249 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/n 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 13.9285(6) _cell_length_b 22.6024(9) _cell_length_c 24.6502(9) _cell_angle_alpha 90.00 _cell_angle_beta 93.3240(10) _cell_angle_gamma 90.00 _cell_volume 7747.3(5) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 5290 _cell_measurement_theta_min 2.45 _cell_measurement_theta_max 21.75 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.33 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.238 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3040 _exptl_absorpt_coefficient_mu 0.488 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7924 _exptl_absorpt_correction_T_max 0.8674 _exptl_absorpt_process_details '(SADABS; Sheldrick, 2004)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 'Bruker-AXS APEX- CCD area-detector' _diffrn_measurement_method '\f and \w' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 51717 _diffrn_reflns_av_R_equivalents 0.0643 _diffrn_reflns_av_sigmaI/netI 0.0659 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 2.81 _diffrn_reflns_theta_max 25.03 _reflns_number_total 13643 _reflns_number_gt 7523 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART, (Bruker, 2004)' _computing_cell_refinement 'Bruker SMART, (Bruker, 2004)' _computing_data_reduction 'Bruker SAINT, (Bruker, 2004)' _computing_structure_solution 'SIR97 (Altomare, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ORTEP3(Farrugia,1997) _computing_publication_material 'WinGX (Farrugia, 1999)' _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. The methoxymethyl groups showed evidence of disorder, particularly in the displacement parameters of terminal methyl C-atom. One of them was modelled over two positions with sof of 53:47, the others could not be successfully modelled. The solvent molecules showed evidence of substantial disorder. However, this could not be successfully modelled. Restraints were applied using DFIX instructions in SHELXL97 (Sheldrick,1997). ; _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^)+(0.1051P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 13643 _refine_ls_number_parameters 921 _refine_ls_number_restraints 5 _refine_ls_R_factor_all 0.1209 _refine_ls_R_factor_gt 0.0588 _refine_ls_wR_factor_ref 0.1804 _refine_ls_wR_factor_gt 0.1572 _refine_ls_goodness_of_fit_ref 0.970 _refine_ls_restrained_S_all 0.972 _refine_ls_shift/su_max 0.009 _refine_ls_shift/su_mean 0.001 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 I1 I 0.53056(3) 0.118326(16) 0.246934(16) 0.08889(18) Uani 1 1 d . . . Na1 Na 0.93336(11) 0.30696(6) 0.24611(5) 0.0447(4) Uani 1 1 d . . . O1 O 1.1723(2) 0.45603(15) 0.22661(11) 0.0707(9) Uani 1 1 d . . . O2 O 1.1135(3) 0.51212(15) 0.07005(13) 0.0834(11) Uani 1 1 d . . . O3 O 0.8838(2) 0.35785(12) 0.01638(10) 0.0535(7) Uani 1 1 d . . . O4 O 0.94266(19) 0.17623(12) 0.03632(10) 0.0507(7) Uani 1 1 d . . . O6 O 0.74136(19) 0.28722(13) 0.24754(10) 0.0547(7) Uani 1 1 d . . . O7 O 1.1603(2) 0.29650(13) 0.04666(11) 0.0557(7) Uani 1 1 d . . . O9 O 1.0912(2) 0.08955(12) 0.23195(11) 0.0617(8) Uani 1 1 d . . . O10 O 1.0898(2) 0.18353(12) 0.44839(10) 0.0535(7) Uani 1 1 d . . . O11 O 1.3942(2) 0.24716(17) 0.39773(13) 0.0823(10) Uani 1 1 d . . . O12 O 1.3289(2) 0.33475(18) 0.26999(13) 0.0928(12) Uani 1 1 d . . . O13 O 0.8568(2) 0.29491(13) 0.47418(10) 0.0543(7) Uani 1 1 d . . . O14 O 0.7844(3) 0.10136(16) 0.42614(15) 0.0960(12) Uani 1 1 d . . . O15 O 0.8600(2) 0.09734(13) 0.27305(12) 0.0673(8) Uani 1 1 d . . . O16 O 1.1359(2) 0.36702(12) 0.46166(10) 0.0545(7) Uani 1 1 d . . . O17 O 0.8713(3) 0.51392(16) 0.44322(14) 0.0890(11) Uani 1 1 d . . . O18 O 0.8538(2) 0.41542(12) 0.24280(10) 0.0553(7) Uani 1 1 d . . . N1 N 1.0270(2) 0.35812(13) 0.17273(10) 0.0348(7) Uani 1 1 d . . . N2 N 1.0007(2) 0.34436(12) 0.12049(11) 0.0352(7) Uani 1 1 d . . . N3 N 0.8800(2) 0.26926(12) 0.11310(10) 0.0340(7) Uani 1 1 d . . . N4 N 0.8397(2) 0.28781(12) 0.15840(11) 0.0354(7) Uani 1 1 d . . . N5 N 1.0282(2) 0.22184(12) 0.18226(11) 0.0361(7) Uani 1 1 d . . . N6 N 1.04515(19) 0.24357(12) 0.13287(10) 0.0328(7) Uani 1 1 d . . . N7 N 1.1129(2) 0.30232(13) 0.31591(11) 0.0390(7) Uani 1 1 d . . . N8 N 1.0966(2) 0.27952(12) 0.36532(11) 0.0349(7) Uani 1 1 d . . . N9 N 0.9264(2) 0.22763(12) 0.32066(10) 0.0354(7) Uani 1 1 d . . . N10 N 0.9341(2) 0.24708(12) 0.37242(10) 0.0346(7) Uani 1 1 d . . . N11 N 0.9205(2) 0.36183(12) 0.33234(10) 0.0348(7) Uani 1 1 d . . . N12 N 0.9721(2) 0.34928(12) 0.37919(10) 0.0347(7) Uani 1 1 d . . . C1 C 0.9793(2) 0.28454(14) 0.10485(13) 0.0323(8) Uani 1 1 d . . . H1 H 0.9888 0.2811 0.0651 0.039 Uiso 1 1 calc R . . C2 C 0.9975(3) 0.39312(16) 0.08786(14) 0.0385(9) Uani 1 1 d . . . C3 C 1.0245(3) 0.43963(16) 0.12072(15) 0.0452(9) Uani 1 1 d . . . C4 C 1.0424(3) 0.41559(16) 0.17217(14) 0.0391(9) Uani 1 1 d . . . C5 C 0.8220(2) 0.23079(15) 0.08377(13) 0.0353(8) Uani 1 1 d . . . C6 C 0.7404(3) 0.22448(16) 0.11067(14) 0.0393(9) Uani 1 1 d . B . C7 C 0.7543(3) 0.26136(16) 0.15672(13) 0.0369(8) Uani 1 1 d . . . C8 C 1.1280(3) 0.22080(16) 0.11341(14) 0.0376(8) Uani 1 1 d . . . C9 C 1.1641(3) 0.18237(16) 0.15170(15) 0.0419(9) Uani 1 1 d . . . C10 C 1.0999(3) 0.18413(15) 0.19357(13) 0.0364(8) Uani 1 1 d . . . C11 C 1.0726(3) 0.44580(18) 0.22441(16) 0.0510(10) Uani 1 1 d . . . H11A H 1.0380 0.4839 0.2269 0.061 Uiso 1 1 calc R . . H11B H 1.0560 0.4207 0.2555 0.061 Uiso 1 1 calc R . . C12 C 1.2030(5) 0.4820(3) 0.2774(2) 0.116(2) Uani 1 1 d . . . H12A H 1.1635 0.5170 0.2838 0.174 Uiso 1 1 calc R . . H12B H 1.2706 0.4938 0.2765 0.174 Uiso 1 1 calc R . . H12C H 1.1959 0.4533 0.3066 0.174 Uiso 1 1 calc R . . C13 C 1.0326(4) 0.50305(19) 0.1015(2) 0.0705(13) Uani 1 1 d . . . H13A H 0.9735 0.5137 0.0795 0.085 Uiso 1 1 calc R . . H13B H 1.0376 0.5296 0.1335 0.085 Uiso 1 1 calc R . . C14 C 1.2004(5) 0.5140(3) 0.1011(3) 0.121(3) Uani 1 1 d . . . H14A H 1.2025 0.5497 0.1237 0.182 Uiso 1 1 calc R . . H14B H 1.2539 0.5148 0.0770 0.182 Uiso 1 1 calc R . . H14C H 1.2060 0.4789 0.1244 0.182 Uiso 1 1 calc R . . C15 C 0.9713(3) 0.38867(18) 0.02856(15) 0.0530(11) Uani 1 1 d . . . H15A H 0.9657 0.4291 0.0132 0.064 Uiso 1 1 calc R . . H15B H 1.0238 0.3682 0.0107 0.064 Uiso 1 1 calc R . . C16 C 0.8031(3) 0.3878(2) 0.03382(18) 0.0676(13) Uani 1 1 d . . . H16A H 0.8120 0.3959 0.0728 0.101 Uiso 1 1 calc R . . H16B H 0.7457 0.3633 0.0268 0.101 Uiso 1 1 calc R . . H16C H 0.7952 0.4253 0.0140 0.101 Uiso 1 1 calc R . . C17 C 0.8512(3) 0.20489(17) 0.03185(14) 0.0464(10) Uani 1 1 d . . . H17A H 0.8020 0.1759 0.0187 0.056 Uiso 1 1 calc R . . H17B H 0.8532 0.2367 0.0043 0.056 Uiso 1 1 calc R . . C18 C 0.9430(4) 0.1237(2) 0.0678(2) 0.0755(14) Uani 1 1 d . . . H18A H 0.9215 0.1328 0.1041 0.113 Uiso 1 1 calc R . . H18B H 1.0083 0.1075 0.0712 0.113 Uiso 1 1 calc R . . H18C H 0.8995 0.0947 0.0501 0.113 Uiso 1 1 calc R . . C19 C 0.6531(3) 0.1874(2) 0.09657(17) 0.0564(11) Uani 1 1 d . . . H19A H 0.6755 0.1514 0.0782 0.068 Uiso 1 1 calc R A 1 H19B H 0.6276 0.1743 0.1313 0.068 Uiso 1 1 calc R A 1 O5 O 0.5751(9) 0.2100(10) 0.0643(7) 0.076(4) Uani 0.53(4) 1 d P B 1 C20 C 0.519(3) 0.238(2) 0.0934(9) 0.135(15) Uani 0.53(4) 1 d P B 1 H20A H 0.5041 0.2137 0.1249 0.202 Uiso 0.53(4) 1 calc PR B 1 H20B H 0.4589 0.2468 0.0720 0.202 Uiso 0.53(4) 1 calc PR B 1 H20C H 0.5490 0.2750 0.1060 0.202 Uiso 0.53(4) 1 calc PR B 1 O5A O 0.5793(9) 0.2309(10) 0.0876(12) 0.065(7) Uani 0.47(4) 1 d P B 2 C20A C 0.4873(13) 0.2043(14) 0.0946(9) 0.077(6) Uani 0.47(4) 1 d P B 2 H20D H 0.4838 0.1661 0.0758 0.115 Uiso 0.47(4) 1 calc PR B 2 H20E H 0.4364 0.2304 0.0793 0.115 Uiso 0.47(4) 1 calc PR B 2 H20F H 0.4789 0.1983 0.1334 0.115 Uiso 0.47(4) 1 calc PR B 2 C21 C 0.6866(3) 0.27263(19) 0.19982(14) 0.0472(10) Uani 1 1 d . . . H21A H 0.6428 0.3056 0.1890 0.057 Uiso 1 1 calc R . . H21B H 0.6475 0.2369 0.2058 0.057 Uiso 1 1 calc R . . C22 C 0.6819(3) 0.3028(3) 0.28981(17) 0.0817(16) Uani 1 1 d . . . H22A H 0.6423 0.3371 0.2786 0.122 Uiso 1 1 calc R . . H22B H 0.7220 0.3129 0.3225 0.122 Uiso 1 1 calc R . . H22C H 0.6401 0.2694 0.2977 0.122 Uiso 1 1 calc R . . C23 C 1.1604(3) 0.23565(18) 0.05874(15) 0.0484(10) Uani 1 1 d . . . H23A H 1.2264 0.2202 0.0558 0.058 Uiso 1 1 calc R . . H23B H 1.1182 0.2151 0.0311 0.058 Uiso 1 1 calc R . . C24 C 1.2274(4) 0.3282(2) 0.0797(2) 0.0778(15) Uani 1 1 d . . . H24A H 1.2039 0.3320 0.1163 0.117 Uiso 1 1 calc R . . H24B H 1.2362 0.3676 0.0643 0.117 Uiso 1 1 calc R . . H24C H 1.2889 0.3071 0.0818 0.117 Uiso 1 1 calc R . . C25 C 1.2517(3) 0.1452(2) 0.14827(18) 0.0677(13) Uani 1 1 d . . . H25A H 1.3096 0.1707 0.1487 0.081 Uiso 1 1 calc R . . H25B H 1.2582 0.1182 0.1799 0.081 Uiso 1 1 calc R . . O8 O 1.2439(4) 0.1128(2) 0.10062(18) 0.137(2) Uani 1 1 d . . . C26 C 1.3228(7) 0.0780(4) 0.0902(3) 0.183(5) Uani 1 1 d . . . H26A H 1.3115 0.0583 0.0549 0.274 Uiso 1 1 calc R . . H26B H 1.3323 0.0481 0.1188 0.274 Uiso 1 1 calc R . . H26C H 1.3802 0.1029 0.0895 0.274 Uiso 1 1 calc R . . C27 C 1.1053(3) 0.15017(16) 0.24473(14) 0.0465(10) Uani 1 1 d . . . H27A H 1.1689 0.1559 0.2641 0.056 Uiso 1 1 calc R . . H27B H 1.0550 0.1639 0.2686 0.056 Uiso 1 1 calc R . . C28 C 1.0901(4) 0.0546(2) 0.2792(2) 0.0837(16) Uani 1 1 d . . . H28A H 1.1538 0.0554 0.2983 0.126 Uiso 1 1 calc R . . H28B H 1.0734 0.0137 0.2692 0.126 Uiso 1 1 calc R . . H28C H 1.0422 0.0703 0.3030 0.126 Uiso 1 1 calc R . . C29 C 1.0066(2) 0.29024(15) 0.38972(13) 0.0334(8) Uani 1 1 d . . . H29 H 1.0185 0.2861 0.4299 0.040 Uiso 1 1 calc R . . C30 C 1.1726(3) 0.24714(16) 0.38696(14) 0.0404(9) Uani 1 1 d . . . C31 C 1.2417(3) 0.24914(16) 0.35014(15) 0.0428(9) Uani 1 1 d . . . C32 C 1.2011(3) 0.28394(16) 0.30685(14) 0.0421(9) Uani 1 1 d . . . C33 C 0.8696(3) 0.22014(16) 0.40345(14) 0.0399(9) Uani 1 1 d . . . C34 C 0.8183(3) 0.18164(17) 0.37042(15) 0.0452(9) Uani 1 1 d . . . C35 C 0.8559(3) 0.18759(15) 0.31942(14) 0.0383(9) Uani 1 1 d . . . C36 C 0.9881(3) 0.39764(16) 0.41109(14) 0.0403(9) Uani 1 1 d . . . C37 C 0.9450(3) 0.44370(17) 0.38333(15) 0.0450(9) Uani 1 1 d . . . C38 C 0.9033(3) 0.41886(16) 0.33522(14) 0.0389(9) Uani 1 1 d . . . C39 C 1.1729(3) 0.21891(18) 0.44117(15) 0.0505(10) Uani 1 1 d . . . H39A H 1.2309 0.1938 0.4464 0.061 Uiso 1 1 calc R . . H39B H 1.1769 0.2501 0.4694 0.061 Uiso 1 1 calc R . . C40 C 1.0823(4) 0.13386(19) 0.4135(2) 0.0747(14) Uani 1 1 d . . . H40A H 1.0795 0.1472 0.3756 0.112 Uiso 1 1 calc R . . H40B H 1.0237 0.1118 0.4203 0.112 Uiso 1 1 calc R . . H40C H 1.1384 0.1082 0.4203 0.112 Uiso 1 1 calc R . . C41 C 1.3389(3) 0.2209(2) 0.35564(19) 0.0646(12) Uani 1 1 d . . . H41A H 1.3320 0.1781 0.3630 0.078 Uiso 1 1 calc R . . H41B H 1.3714 0.2253 0.3212 0.078 Uiso 1 1 calc R . . C42 C 1.4869(4) 0.2210(3) 0.4042(3) 0.114(2) Uani 1 1 d . . . H42A H 1.4803 0.1780 0.4080 0.170 Uiso 1 1 calc R . . H42B H 1.5212 0.2371 0.4367 0.170 Uiso 1 1 calc R . . H42C H 1.5232 0.2297 0.3722 0.170 Uiso 1 1 calc R . . C43 C 1.2458(3) 0.3010(2) 0.25627(16) 0.0549(11) Uani 1 1 d . . . H43A H 1.2632 0.2651 0.2360 0.066 Uiso 1 1 calc R . . H43B H 1.1999 0.3245 0.2329 0.066 Uiso 1 1 calc R . . C44 C 1.3788(5) 0.3490(4) 0.2238(3) 0.167(4) Uani 1 1 d . . . H44A H 1.3947 0.3126 0.2047 0.251 Uiso 1 1 calc R . . H44B H 1.4381 0.3701 0.2350 0.251 Uiso 1 1 calc R . . H44C H 1.3383 0.3742 0.1996 0.251 Uiso 1 1 calc R . . C45 C 0.8631(3) 0.23334(19) 0.46236(15) 0.0527(11) Uani 1 1 d . . . H45A H 0.8058 0.2132 0.4755 0.063 Uiso 1 1 calc R . . H45B H 0.9204 0.2168 0.4826 0.063 Uiso 1 1 calc R . . C46 C 0.7760(3) 0.3230(2) 0.44884(17) 0.0666(13) Uani 1 1 d . . . H46A H 0.7873 0.3302 0.4105 0.100 Uiso 1 1 calc R . . H46B H 0.7649 0.3607 0.4670 0.100 Uiso 1 1 calc R . . H46C H 0.7194 0.2976 0.4513 0.100 Uiso 1 1 calc R . . C47 C 0.7411(4) 0.1411(2) 0.38704(19) 0.0697(13) Uani 1 1 d . . . H47A H 0.6890 0.1638 0.4031 0.084 Uiso 1 1 calc R . . H47B H 0.7134 0.1189 0.3552 0.084 Uiso 1 1 calc R . . C48 C 0.7188(6) 0.0605(3) 0.4436(3) 0.144(3) Uani 1 1 d . . . H48A H 0.6799 0.0787 0.4709 0.216 Uiso 1 1 calc R . . H48B H 0.7533 0.0263 0.4595 0.216 Uiso 1 1 calc R . . H48C H 0.6767 0.0475 0.4126 0.216 Uiso 1 1 calc R . . C49 C 0.8279(3) 0.15638(17) 0.26801(15) 0.0494(10) Uani 1 1 d . . . H49A H 0.7572 0.1574 0.2612 0.059 Uiso 1 1 calc R . . H49B H 0.8576 0.1759 0.2372 0.059 Uiso 1 1 calc R . . C50 C 0.8428(4) 0.0662(2) 0.2236(2) 0.0929(18) Uani 1 1 d . . . H50A H 0.7739 0.0669 0.2131 0.139 Uiso 1 1 calc R . . H50B H 0.8642 0.0251 0.2283 0.139 Uiso 1 1 calc R . . H50C H 0.8785 0.0851 0.1951 0.139 Uiso 1 1 calc R . . C51 C 1.0443(3) 0.39407(19) 0.46450(15) 0.0543(11) Uani 1 1 d . . . H51A H 1.0533 0.4346 0.4792 0.065 Uiso 1 1 calc R . . H51B H 1.0065 0.3714 0.4902 0.065 Uiso 1 1 calc R . . C52 C 1.1995(4) 0.3994(2) 0.4313(2) 0.0773(15) Uani 1 1 d . . . H52A H 1.1724 0.4038 0.3939 0.116 Uiso 1 1 calc R . . H52B H 1.2612 0.3785 0.4311 0.116 Uiso 1 1 calc R . . H52C H 1.2096 0.4386 0.4476 0.116 Uiso 1 1 calc R . . C53 C 0.9388(4) 0.50599(19) 0.40368(19) 0.0653(12) Uani 1 1 d . . . H53A H 1.0030 0.5181 0.4192 0.078 Uiso 1 1 calc R . . H53B H 0.9218 0.5324 0.3725 0.078 Uiso 1 1 calc R . . C54 C 0.7765(5) 0.5082(3) 0.4225(2) 0.109(2) Uani 1 1 d . . . H54A H 0.7643 0.5363 0.3927 0.164 Uiso 1 1 calc R . . H54B H 0.7327 0.5164 0.4513 0.164 Uiso 1 1 calc R . . H54C H 0.7657 0.4678 0.4090 0.164 Uiso 1 1 calc R . . C55 C 0.8454(3) 0.44838(17) 0.29002(15) 0.0481(10) Uani 1 1 d . . . H55A H 0.7771 0.4507 0.2989 0.058 Uiso 1 1 calc R . . H55B H 0.8692 0.4891 0.2847 0.058 Uiso 1 1 calc R . . C56 C 0.7954(4) 0.4384(2) 0.19847(17) 0.0802(16) Uani 1 1 d . . . H56A H 0.7276 0.4363 0.2069 0.120 Uiso 1 1 calc R . . H56B H 0.8054 0.4150 0.1658 0.120 Uiso 1 1 calc R . . H56C H 0.8130 0.4797 0.1921 0.120 Uiso 1 1 calc R . . O80 O 0.4565(14) 0.4638(9) 0.0873(12) 0.316(12) Uani 0.50 1 d P . . C80 C 0.5516(15) 0.4661(10) 0.1195(8) 0.221(13) Uani 0.50 1 d PD . . H80A H 0.5808 0.5060 0.1183 0.266 Uiso 0.50 1 calc PR . . H80B H 0.5449 0.4546 0.1579 0.266 Uiso 0.50 1 calc PR . . C81 C 0.5975(11) 0.4307(11) 0.0962(9) 0.200(11) Uani 0.50 1 d P . . H81A H 0.6161 0.3978 0.1211 0.240 Uiso 0.50 1 calc PR . . H81B H 0.6571 0.4495 0.0845 0.240 Uiso 0.50 1 calc PR . . C82 C 0.5506(18) 0.4109(14) 0.0559(9) 0.298(19) Uani 0.50 1 d PD . . H82A H 0.5742 0.3708 0.0473 0.358 Uiso 0.50 1 calc PR . . H82B H 0.5595 0.4367 0.0241 0.358 Uiso 0.50 1 calc PR . . C83 C 0.4628(16) 0.4083(10) 0.0648(12) 0.248(15) Uani 0.50 1 d PD . . H83A H 0.4485 0.3765 0.0908 0.297 Uiso 0.50 1 calc PR . . H83B H 0.4214 0.4039 0.0310 0.297 Uiso 0.50 1 calc PR . . O90 O 1.0400(14) -0.0408(7) 0.0769(6) 0.227(7) Uani 0.50 1 d PD . . C90 C 1.0417(16) -0.0338(9) 0.1342(7) 0.188(10) Uani 0.50 1 d PD . . H90A H 1.0996 -0.0532 0.1514 0.226 Uiso 0.50 1 calc PR . . H90B H 1.0440 0.0087 0.1437 0.226 Uiso 0.50 1 calc PR . . C91 C 0.9603(14) -0.0591(8) 0.1528(7) 0.163(8) Uani 0.50 1 d PD . . H91A H 0.9721 -0.0731 0.1906 0.196 Uiso 0.50 1 calc PR . . H91B H 0.9067 -0.0303 0.1515 0.196 Uiso 0.50 1 calc PR . . C92 C 0.9415(15) -0.1011(7) 0.1220(7) 0.180(10) Uani 0.50 1 d PD . . H92A H 0.9684 -0.1380 0.1382 0.217 Uiso 0.50 1 calc PR . . H92B H 0.8709 -0.1058 0.1167 0.217 Uiso 0.50 1 calc PR . . C93 C 0.9777(18) -0.0916(8) 0.0758(7) 0.204(11) Uani 0.50 1 d PD . . H93A H 0.9249 -0.0856 0.0477 0.245 Uiso 0.50 1 calc PR . . H93B H 1.0146 -0.1269 0.0656 0.245 Uiso 0.50 1 calc PR . . 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 I1 0.0881(3) 0.0750(3) 0.1036(3) 0.00285(19) 0.0061(2) -0.02110(19) Na1 0.0611(9) 0.0461(9) 0.0271(7) -0.0016(6) 0.0052(7) -0.0061(7) O1 0.064(2) 0.101(2) 0.0463(17) -0.0035(16) -0.0045(15) -0.0269(18) O2 0.095(3) 0.080(2) 0.074(2) 0.0382(18) -0.009(2) -0.038(2) O3 0.068(2) 0.0547(17) 0.0364(15) -0.0019(13) -0.0071(14) 0.0058(15) O4 0.0514(17) 0.0531(17) 0.0487(16) -0.0142(13) 0.0108(13) 0.0052(13) O6 0.0476(16) 0.083(2) 0.0341(14) -0.0135(14) 0.0080(13) 0.0024(14) O7 0.0549(18) 0.066(2) 0.0479(16) 0.0095(14) 0.0166(14) -0.0018(15) O9 0.090(2) 0.0456(17) 0.0507(17) 0.0058(14) 0.0117(15) 0.0023(15) O10 0.0650(19) 0.0533(17) 0.0424(15) 0.0124(13) 0.0039(13) -0.0006(14) O11 0.0482(19) 0.124(3) 0.073(2) -0.001(2) -0.0097(17) 0.0149(19) O12 0.076(2) 0.137(3) 0.066(2) 0.011(2) 0.0133(18) -0.045(2) O13 0.0605(19) 0.069(2) 0.0342(15) -0.0077(13) 0.0087(13) 0.0040(15) O14 0.108(3) 0.086(3) 0.096(3) 0.034(2) 0.013(2) -0.033(2) O15 0.085(2) 0.0480(18) 0.070(2) -0.0150(15) 0.0119(17) -0.0066(16) O16 0.0584(19) 0.0595(18) 0.0439(16) 0.0051(13) -0.0129(14) -0.0076(15) O17 0.109(3) 0.087(3) 0.070(2) -0.0405(19) -0.008(2) 0.027(2) O18 0.073(2) 0.0577(18) 0.0340(14) -0.0023(13) -0.0063(13) 0.0178(15) N1 0.0406(17) 0.0389(18) 0.0247(15) -0.0015(13) -0.0001(13) -0.0038(14) N2 0.0405(17) 0.0375(17) 0.0278(16) 0.0025(13) 0.0040(13) -0.0019(14) N3 0.0356(16) 0.0417(17) 0.0253(15) -0.0009(13) 0.0055(13) -0.0007(14) N4 0.0399(18) 0.0388(17) 0.0283(16) -0.0060(13) 0.0091(13) 0.0019(14) N5 0.0447(18) 0.0388(17) 0.0253(15) 0.0017(12) 0.0078(13) 0.0017(14) N6 0.0379(17) 0.0362(16) 0.0248(15) 0.0022(12) 0.0071(13) 0.0007(13) N7 0.0398(18) 0.0456(18) 0.0318(16) 0.0044(13) 0.0051(14) -0.0015(14) N8 0.0360(17) 0.0406(17) 0.0282(16) 0.0050(13) 0.0017(13) 0.0013(14) N9 0.0444(18) 0.0375(17) 0.0242(15) -0.0036(12) 0.0022(13) -0.0008(14) N10 0.0385(17) 0.0393(17) 0.0260(15) -0.0021(13) 0.0029(13) -0.0004(14) N11 0.0388(17) 0.0375(17) 0.0273(16) -0.0023(12) -0.0044(13) 0.0070(13) N12 0.0397(17) 0.0395(18) 0.0245(15) -0.0020(13) -0.0006(13) 0.0022(14) C1 0.035(2) 0.036(2) 0.0257(17) -0.0017(15) 0.0057(15) -0.0020(16) C2 0.042(2) 0.040(2) 0.034(2) 0.0096(17) 0.0041(17) -0.0012(17) C3 0.048(2) 0.040(2) 0.048(2) 0.0072(18) 0.0019(19) -0.0048(18) C4 0.037(2) 0.041(2) 0.039(2) -0.0012(17) 0.0027(17) -0.0060(17) C5 0.039(2) 0.038(2) 0.0286(18) -0.0021(15) -0.0004(16) 0.0003(16) C6 0.037(2) 0.045(2) 0.035(2) -0.0008(16) -0.0023(17) -0.0001(17) C7 0.039(2) 0.043(2) 0.0291(19) 0.0004(16) 0.0018(16) 0.0033(17) C8 0.038(2) 0.043(2) 0.0324(19) -0.0034(16) 0.0092(16) 0.0047(17) C9 0.040(2) 0.044(2) 0.041(2) -0.0047(17) 0.0042(18) 0.0108(17) C10 0.043(2) 0.033(2) 0.033(2) -0.0013(15) 0.0051(17) 0.0012(17) C11 0.053(3) 0.047(2) 0.053(2) -0.0081(19) 0.000(2) -0.010(2) C12 0.103(5) 0.173(7) 0.070(4) -0.024(4) -0.010(3) -0.062(5) C13 0.084(4) 0.050(3) 0.077(3) 0.016(2) -0.008(3) -0.008(2) C14 0.092(5) 0.150(6) 0.119(5) 0.056(5) -0.021(4) -0.058(4) C15 0.063(3) 0.056(3) 0.039(2) 0.0168(19) 0.000(2) -0.002(2) C16 0.067(3) 0.077(3) 0.057(3) -0.017(2) -0.013(2) 0.007(3) C17 0.051(2) 0.056(3) 0.032(2) -0.0074(18) -0.0005(18) -0.004(2) C18 0.080(4) 0.054(3) 0.093(4) -0.006(3) 0.007(3) 0.014(2) C19 0.040(2) 0.076(3) 0.054(3) -0.008(2) 0.004(2) -0.014(2) O5 0.051(5) 0.122(9) 0.053(6) -0.015(6) -0.010(4) -0.013(5) C20 0.16(3) 0.17(3) 0.064(10) -0.047(13) -0.050(15) 0.08(3) O5A 0.026(5) 0.080(10) 0.087(14) 0.009(9) -0.015(6) -0.010(5) C20A 0.027(7) 0.131(17) 0.074(9) -0.013(10) 0.012(6) -0.010(9) C21 0.038(2) 0.066(3) 0.038(2) -0.0047(19) 0.0057(18) -0.0009(19) C22 0.066(3) 0.137(5) 0.044(3) -0.024(3) 0.020(2) -0.003(3) C23 0.050(2) 0.060(3) 0.037(2) -0.0048(19) 0.0143(18) 0.003(2) C24 0.073(3) 0.080(4) 0.083(4) 0.006(3) 0.029(3) -0.010(3) C25 0.069(3) 0.074(3) 0.062(3) -0.002(2) 0.016(2) 0.027(3) O8 0.171(5) 0.144(4) 0.097(3) -0.020(3) 0.026(3) 0.104(4) C26 0.256(11) 0.156(7) 0.143(7) 0.003(6) 0.066(7) 0.135(8) C27 0.063(3) 0.038(2) 0.039(2) 0.0009(17) 0.0021(19) 0.0092(19) C28 0.128(5) 0.053(3) 0.072(3) 0.022(3) 0.018(3) 0.014(3) C29 0.041(2) 0.038(2) 0.0209(17) -0.0010(15) -0.0005(15) 0.0001(16) C30 0.039(2) 0.044(2) 0.037(2) 0.0018(17) -0.0034(17) 0.0034(17) C31 0.036(2) 0.048(2) 0.044(2) -0.0061(18) 0.0014(18) 0.0053(17) C32 0.040(2) 0.049(2) 0.038(2) -0.0044(17) 0.0062(18) -0.0059(18) C33 0.041(2) 0.047(2) 0.033(2) 0.0102(17) 0.0114(17) 0.0002(18) C34 0.045(2) 0.048(2) 0.043(2) 0.0064(18) 0.0047(19) -0.0070(19) C35 0.039(2) 0.037(2) 0.039(2) -0.0007(16) 0.0064(17) -0.0013(17) C36 0.045(2) 0.044(2) 0.032(2) -0.0121(17) 0.0026(17) -0.0020(18) C37 0.052(2) 0.040(2) 0.043(2) -0.0086(18) 0.0020(19) -0.0007(19) C38 0.040(2) 0.041(2) 0.037(2) -0.0052(17) 0.0058(17) 0.0075(17) C39 0.056(3) 0.054(3) 0.041(2) 0.0116(19) -0.0031(19) 0.006(2) C40 0.099(4) 0.046(3) 0.079(3) -0.001(2) 0.000(3) 0.000(3) C41 0.044(3) 0.082(3) 0.068(3) -0.010(2) 0.002(2) 0.009(2) C42 0.049(3) 0.185(7) 0.106(5) 0.031(4) -0.001(3) 0.033(4) C43 0.040(2) 0.078(3) 0.048(2) 0.000(2) 0.0113(19) -0.011(2) C44 0.116(6) 0.292(11) 0.099(5) 0.010(6) 0.044(4) -0.113(7) C45 0.058(3) 0.068(3) 0.033(2) 0.0073(19) 0.0113(19) -0.001(2) C46 0.070(3) 0.085(3) 0.046(3) 0.003(2) 0.016(2) 0.015(3) C47 0.071(3) 0.075(3) 0.064(3) 0.007(3) 0.011(3) -0.025(3) C48 0.164(7) 0.107(5) 0.166(7) 0.038(5) 0.051(6) -0.052(5) C49 0.053(2) 0.049(2) 0.046(2) -0.0071(19) 0.0020(19) -0.015(2) C50 0.115(5) 0.071(4) 0.093(4) -0.040(3) 0.013(3) -0.030(3) C51 0.070(3) 0.057(3) 0.035(2) -0.0111(18) -0.005(2) -0.010(2) C52 0.061(3) 0.087(4) 0.082(3) 0.027(3) -0.008(3) -0.014(3) C53 0.075(3) 0.053(3) 0.067(3) -0.018(2) -0.005(3) 0.000(2) C54 0.098(5) 0.124(5) 0.103(5) -0.046(4) -0.016(4) 0.045(4) C55 0.057(3) 0.045(2) 0.042(2) -0.0039(18) -0.0023(19) 0.0125(19) C56 0.099(4) 0.098(4) 0.041(3) -0.001(2) -0.016(3) 0.037(3) O80 0.196(17) 0.229(19) 0.52(4) -0.05(2) -0.01(2) 0.127(15) C80 0.175(17) 0.28(2) 0.200(19) -0.192(19) -0.104(15) 0.129(18) C81 0.091(11) 0.31(3) 0.20(2) -0.16(2) -0.005(12) 0.038(14) C82 0.21(3) 0.54(5) 0.152(18) -0.23(3) 0.053(18) 0.04(3) C83 0.17(2) 0.17(2) 0.40(4) -0.15(2) -0.01(2) -0.111(18) O90 0.31(2) 0.201(15) 0.177(14) 0.045(11) 0.108(14) -0.017(14) C90 0.21(2) 0.23(2) 0.113(14) -0.041(13) -0.096(14) -0.101(17) C91 0.21(2) 0.165(16) 0.125(13) -0.073(12) 0.088(14) 0.035(14) C92 0.29(2) 0.139(14) 0.134(13) -0.016(11) 0.153(16) -0.096(14) C93 0.37(3) 0.106(13) 0.146(16) -0.090(12) 0.055(19) -0.088(17) _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 Na1 N11 2.476(3) . ? Na1 N4 2.497(3) . ? Na1 N1 2.566(3) . ? Na1 N9 2.573(3) . ? Na1 O18 2.690(3) . ? Na1 O6 2.713(3) . ? Na1 N5 2.857(3) . ? Na1 N7 2.954(3) . ? O1 C11 1.406(5) . ? O1 C12 1.425(6) . ? O2 C14 1.395(6) . ? O2 C13 1.418(6) . ? O3 C16 1.401(5) . ? O3 C15 1.421(5) . ? O4 C18 1.418(5) . ? O4 C17 1.427(5) . ? O6 C21 1.403(4) . ? O6 C22 1.413(5) . ? O7 C24 1.400(6) . ? O7 C23 1.407(5) . ? O9 C28 1.409(5) . ? O9 C27 1.417(5) . ? O10 C40 1.415(5) . ? O10 C39 1.426(5) . ? O11 C41 1.389(5) . ? O11 C42 1.421(6) . ? O12 C44 1.404(6) . ? O12 C43 1.412(5) . ? O13 C46 1.407(5) . ? O13 C45 1.426(5) . ? O14 C48 1.385(6) . ? O14 C47 1.425(6) . ? O15 C49 1.410(5) . ? O15 C50 1.416(5) . ? O16 C52 1.399(5) . ? O16 C51 1.420(5) . ? O17 C54 1.394(7) . ? O17 C53 1.404(6) . ? O18 C55 1.393(4) . ? O18 C56 1.422(5) . ? N1 C4 1.317(4) . ? N1 N2 1.354(4) . ? N2 C2 1.363(4) . ? N2 C1 1.433(4) . ? N3 N4 1.346(4) . ? N3 C5 1.365(4) . ? N3 C1 1.450(4) . ? N4 C7 1.329(4) . ? N5 C10 1.330(4) . ? N5 N6 1.346(4) . ? N6 C8 1.376(4) . ? N6 C1 1.450(4) . ? N7 C32 1.327(5) . ? N7 N8 1.354(4) . ? N8 C30 1.369(4) . ? N8 C29 1.441(4) . ? N9 C35 1.334(4) . ? N9 N10 1.348(4) . ? N10 C33 1.358(4) . ? N10 C29 1.450(4) . ? N11 C38 1.314(4) . ? N11 N12 1.354(4) . ? N12 C36 1.357(4) . ? N12 C29 1.437(4) . ? C2 C3 1.366(5) . ? C2 C15 1.489(5) . ? C3 C4 1.389(5) . ? C3 C13 1.516(6) . ? C4 C11 1.496(5) . ? C5 C6 1.356(5) . ? C5 C17 1.486(5) . ? C6 C7 1.413(5) . ? C6 C19 1.501(5) . ? C7 C21 1.482(5) . ? C8 C9 1.357(5) . ? C8 C23 1.484(5) . ? C9 C10 1.405(5) . ? C9 C25 1.488(5) . ? C10 C27 1.475(5) . ? C19 O5 1.405(13) . ? C19 O5A 1.431(16) . ? O5 C20 1.26(3) . ? O5A C20A 1.43(3) . ? C25 O8 1.383(6) . ? O8 C26 1.387(7) . ? C30 C31 1.361(5) . ? C30 C39 1.481(5) . ? C31 C32 1.417(5) . ? C31 C41 1.496(5) . ? C32 C43 1.477(5) . ? C33 C34 1.365(5) . ? C33 C45 1.490(5) . ? C34 C35 1.397(5) . ? C34 C47 1.489(5) . ? C35 C49 1.483(5) . ? C36 C37 1.365(5) . ? C36 C51 1.494(5) . ? C37 C38 1.407(5) . ? C37 C53 1.499(6) . ? C38 C55 1.495(5) . ? O80 C83 1.38(2) . ? O80 C80 1.51(2) . ? C80 C81 1.194(18) . ? C80 C82 2.005(15) . ? C81 C82 1.24(2) . ? C81 C83 2.05(2) . ? C82 C83 1.256(17) . ? O90 C90 1.422(15) . ? O90 C93 1.44(2) . ? C90 C91 1.37(2) . ? C91 C92 1.233(14) . ? C91 C93 2.060(17) . ? C92 C93 1.289(15) . ? 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 N11 Na1 N4 140.34(11) . . ? N11 Na1 N1 116.38(11) . . ? N4 Na1 N1 74.28(9) . . ? N11 Na1 N9 74.24(9) . . ? N4 Na1 N9 117.26(10) . . ? N1 Na1 N9 149.23(11) . . ? N11 Na1 O18 61.28(9) . . ? N4 Na1 O18 86.44(9) . . ? N1 Na1 O18 78.07(9) . . ? N9 Na1 O18 128.63(9) . . ? N11 Na1 O6 87.19(9) . . ? N4 Na1 O6 61.11(9) . . ? N1 Na1 O6 128.67(10) . . ? N9 Na1 O6 78.36(10) . . ? O18 Na1 O6 75.26(10) . . ? N11 Na1 N5 150.30(11) . . ? N4 Na1 N5 68.99(9) . . ? N1 Na1 N5 69.21(9) . . ? N9 Na1 N5 87.81(9) . . ? O18 Na1 N5 143.12(9) . . ? O6 Na1 N5 112.58(9) . . ? N11 Na1 N7 67.58(9) . . ? N4 Na1 N7 151.67(10) . . ? N1 Na1 N7 88.79(9) . . ? N9 Na1 N7 67.97(9) . . ? O18 Na1 N7 112.55(9) . . ? O6 Na1 N7 142.03(9) . . ? N5 Na1 N7 83.92(9) . . ? C11 O1 C12 110.3(4) . . ? C14 O2 C13 113.3(4) . . ? C16 O3 C15 113.1(3) . . ? C18 O4 C17 113.4(3) . . ? C21 O6 C22 111.3(3) . . ? C21 O6 Na1 121.0(2) . . ? C22 O6 Na1 126.1(2) . . ? C24 O7 C23 112.6(3) . . ? C28 O9 C27 111.5(3) . . ? C40 O10 C39 113.6(3) . . ? C41 O11 C42 111.5(4) . . ? C44 O12 C43 111.5(4) . . ? C46 O13 C45 114.0(3) . . ? C48 O14 C47 111.6(5) . . ? C49 O15 C50 110.9(4) . . ? C52 O16 C51 113.6(3) . . ? C54 O17 C53 113.1(4) . . ? C55 O18 C56 112.0(3) . . ? C55 O18 Na1 121.1(2) . . ? C56 O18 Na1 124.9(2) . . ? C4 N1 N2 104.6(3) . . ? C4 N1 Na1 122.8(2) . . ? N2 N1 Na1 116.5(2) . . ? N1 N2 C2 111.9(3) . . ? N1 N2 C1 120.9(3) . . ? C2 N2 C1 127.2(3) . . ? N4 N3 C5 112.0(3) . . ? N4 N3 C1 119.3(3) . . ? C5 N3 C1 128.1(3) . . ? C7 N4 N3 104.5(3) . . ? C7 N4 Na1 121.8(2) . . ? N3 N4 Na1 123.4(2) . . ? C10 N5 N6 104.7(3) . . ? C10 N5 Na1 133.0(2) . . ? N6 N5 Na1 111.31(19) . . ? N5 N6 C8 111.9(3) . . ? N5 N6 C1 121.6(3) . . ? C8 N6 C1 126.4(3) . . ? C32 N7 N8 103.8(3) . . ? C32 N7 Na1 132.3(2) . . ? N8 N7 Na1 110.88(19) . . ? N7 N8 C30 112.8(3) . . ? N7 N8 C29 120.5(3) . . ? C30 N8 C29 126.8(3) . . ? C35 N9 N10 105.1(3) . . ? C35 N9 Na1 121.0(2) . . ? N10 N9 Na1 116.4(2) . . ? N9 N10 C33 111.6(3) . . ? N9 N10 C29 120.9(3) . . ? C33 N10 C29 127.5(3) . . ? C38 N11 N12 104.4(3) . . ? C38 N11 Na1 124.1(2) . . ? N12 N11 Na1 124.5(2) . . ? N11 N12 C36 112.7(3) . . ? N11 N12 C29 120.2(3) . . ? C36 N12 C29 127.0(3) . . ? N2 C1 N3 111.9(3) . . ? N2 C1 N6 111.0(3) . . ? N3 C1 N6 111.3(3) . . ? N2 C2 C3 105.9(3) . . ? N2 C2 C15 121.5(3) . . ? C3 C2 C15 132.6(3) . . ? C2 C3 C4 105.6(3) . . ? C2 C3 C13 124.4(4) . . ? C4 C3 C13 130.0(4) . . ? N1 C4 C3 112.0(3) . . ? N1 C4 C11 118.6(3) . . ? C3 C4 C11 129.4(3) . . ? C6 C5 N3 107.2(3) . . ? C6 C5 C17 131.2(3) . . ? N3 C5 C17 121.6(3) . . ? C5 C6 C7 104.6(3) . . ? C5 C6 C19 129.5(3) . . ? C7 C6 C19 125.9(3) . . ? N4 C7 C6 111.8(3) . . ? N4 C7 C21 120.3(3) . . ? C6 C7 C21 127.9(3) . . ? C9 C8 N6 106.3(3) . . ? C9 C8 C23 131.0(3) . . ? N6 C8 C23 122.5(3) . . ? C8 C9 C10 105.5(3) . . ? C8 C9 C25 126.4(3) . . ? C10 C9 C25 128.1(4) . . ? N5 C10 C9 111.5(3) . . ? N5 C10 C27 120.9(3) . . ? C9 C10 C27 127.6(3) . . ? O1 C11 C4 109.6(3) . . ? O2 C13 C3 112.6(4) . . ? O3 C15 C2 113.5(3) . . ? O4 C17 C5 113.6(3) . . ? O5 C19 O5A 30.3(6) . . ? O5 C19 C6 121.1(9) . . ? O5A C19 C6 102.5(9) . . ? C20 O5 C19 110.3(17) . . ? C19 O5A C20A 109.4(18) . . ? O6 C21 C7 107.7(3) . . ? O7 C23 C8 114.6(3) . . ? O8 C25 C9 108.8(4) . . ? C25 O8 C26 115.7(6) . . ? O9 C27 C10 108.3(3) . . ? N12 C29 N8 111.7(3) . . ? N12 C29 N10 110.6(3) . . ? N8 C29 N10 111.8(3) . . ? C31 C30 N8 106.4(3) . . ? C31 C30 C39 130.6(3) . . ? N8 C30 C39 122.9(3) . . ? C30 C31 C32 104.7(3) . . ? C30 C31 C41 126.6(4) . . ? C32 C31 C41 128.7(4) . . ? N7 C32 C31 112.3(3) . . ? N7 C32 C43 120.0(3) . . ? C31 C32 C43 127.7(4) . . ? N10 C33 C34 106.9(3) . . ? N10 C33 C45 122.6(3) . . ? C34 C33 C45 130.5(3) . . ? C33 C34 C35 105.3(3) . . ? C33 C34 C47 126.2(3) . . ? C35 C34 C47 128.5(4) . . ? N9 C35 C34 111.0(3) . . ? N9 C35 C49 119.9(3) . . ? C34 C35 C49 129.0(3) . . ? N12 C36 C37 105.7(3) . . ? N12 C36 C51 121.8(3) . . ? C37 C36 C51 132.5(3) . . ? C36 C37 C38 105.4(3) . . ? C36 C37 C53 125.5(4) . . ? C38 C37 C53 128.9(4) . . ? N11 C38 C37 111.7(3) . . ? N11 C38 C55 119.3(3) . . ? C37 C38 C55 129.0(3) . . ? O10 C39 C30 113.2(3) . . ? O11 C41 C31 110.2(3) . . ? O12 C43 C32 108.6(3) . . ? O13 C45 C33 113.7(3) . . ? O14 C47 C34 106.8(4) . . ? O15 C49 C35 108.0(3) . . ? O16 C51 C36 114.0(3) . . ? O17 C53 C37 114.0(4) . . ? O18 C55 C38 108.4(3) . . ? C83 O80 C80 99.8(15) . . ? C81 C80 O80 101.6(13) . . ? C81 C80 C82 35.3(11) . . ? O80 C80 C82 66.4(11) . . ? C80 C81 C82 110.9(18) . . ? C80 C81 C83 81.0(13) . . ? C82 C81 C83 35.0(10) . . ? C81 C82 C83 110.4(17) . . ? C81 C82 C80 33.8(9) . . ? C83 C82 C80 81.6(12) . . ? C82 C83 O80 96.5(16) . . ? C82 C83 C81 34.5(10) . . ? O80 C83 C81 72.6(11) . . ? C90 O90 C93 94.6(11) . . ? C91 C90 O90 108.6(13) . . ? C92 C91 C90 105.5(12) . . ? C92 C91 C93 36.1(7) . . ? C90 C91 C93 72.4(9) . . ? C93 C92 C91 109.5(13) . . ? C92 C93 O90 112.6(12) . . ? C92 C93 C91 34.3(7) . . ? O90 C93 C91 78.6(9) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.572 _refine_diff_density_min -0.503 _refine_diff_density_rms 0.072 _vrf_PLAT220_na-bolck ; PROBLEM: Large Non-Solvent C Ueq(max)/Ueq(min) ... 5.70 Ratio RESPONSE: The methoxymethyl groups showed evidence of disorder, particularly in the displacement parameters of terminal methyl C-atom. One of them was modelled over two positions with sof of 53:47, the others could not be successfully modelled. ; _vrf_PLAT222_na-bolck ; PROBLEM: Large Non-Solvent H Ueq(max)/Ueq(min) ... 7.03 Ratio RESPONSE: The methoxymethyl groups showed evidence of disorder, particularly in the displacement parameters of terminal methyl C-atom. One of them was modelled over two positions with sof of 53:47, the others could not be successfully modelled. ; _vrf_PLAT773_na-bolck ; PROBLEM: Suspect C-C Bond in CIF: C80 -- C82 .. 2.01 Ang. RESPONSE: The solvent molecules showed evidence of substantial disorder. However, this could not be successfully modelled. Restraints were applied using DFIX instructions in SHELXL97 (Sheldrick,1997). ; # end Validation Reply Form # Attachment 'compound_1.cif' data_compound1 _database_code_depnum_ccdc_archive 'CCDC 697209' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C44 H68 N12 Na O12, I' _chemical_formula_sum 'C44 H68 I N12 Na O12' _chemical_formula_weight 1106.99 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' Na Na 0.0362 0.0249 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting trigonal _symmetry_space_group_name_H-M 'R -3 c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'x-y, -y, -z+1/2' '-x, -x+y, -z+1/2' 'y, x, -z+1/2' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' 'x-y+2/3, -y+1/3, -z+5/6' '-x+2/3, -x+y+1/3, -z+5/6' 'y+2/3, x+1/3, -z+5/6' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' 'x-y+1/3, -y+2/3, -z+7/6' '-x+1/3, -x+y+2/3, -z+7/6' 'y+1/3, x+2/3, -z+7/6' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' '-x+y, y, z-1/2' 'x, x-y, z-1/2' '-y, -x, z-1/2' '-x+2/3, -y+1/3, -z+1/3' 'y+2/3, -x+y+1/3, -z+1/3' 'x-y+2/3, x+1/3, -z+1/3' '-x+y+2/3, y+1/3, z-1/6' 'x+2/3, x-y+1/3, z-1/6' '-y+2/3, -x+1/3, z-1/6' '-x+1/3, -y+2/3, -z+2/3' 'y+1/3, -x+y+2/3, -z+2/3' 'x-y+1/3, x+2/3, -z+2/3' '-x+y+1/3, y+2/3, z+1/6' 'x+1/3, x-y+2/3, z+1/6' '-y+1/3, -x+2/3, z+1/6' _cell_length_a 12.4457(2) _cell_length_b 12.4457(2) _cell_length_c 57.2653(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 7681.8(2) _cell_formula_units_Z 6 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 5765 _cell_measurement_theta_min 3.27 _cell_measurement_theta_max 24.40 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.436 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3456 _exptl_absorpt_coefficient_mu 0.704 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9078 _exptl_absorpt_correction_T_max 0.9590 _exptl_absorpt_process_details '(SADABS; Sheldrick, 2004)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-AXS APEX- CCD area-detector' _diffrn_measurement_method '\f and \w' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 29433 _diffrn_reflns_av_R_equivalents 0.0755 _diffrn_reflns_av_sigmaI/netI 0.0285 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -69 _diffrn_reflns_limit_l_max 69 _diffrn_reflns_theta_min 3.27 _diffrn_reflns_theta_max 25.69 _reflns_number_total 1627 _reflns_number_gt 1265 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART, (Bruker, 2004)' _computing_cell_refinement 'Bruker SMART, (Bruker, 2004)' _computing_data_reduction 'Bruker SAINT, (Bruker, 2004)' _computing_structure_solution 'SIR97 (Altomare, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SCHAKAL(Keller,1989),ORTEP3(Farrugia,1997) _computing_publication_material 'WinGX (Farrugia, 1999)' _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^)+(0.0329P)^2^+5.8147P] 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 1627 _refine_ls_number_parameters 109 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0445 _refine_ls_R_factor_gt 0.0286 _refine_ls_wR_factor_ref 0.0703 _refine_ls_wR_factor_gt 0.0665 _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_restrained_S_all 1.027 _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 I1 I -0.3333 0.3333 0.5833 0.05433(17) Uani 1 6 d S . . Na1 Na 0.0000 0.0000 0.5000 0.0151(3) Uani 1 6 d S . . O1 O -0.18695(15) -0.00539(13) 0.59031(2) 0.0410(4) Uani 1 1 d . . . O2 O 0.10650(12) 0.42885(11) 0.50912(2) 0.0263(3) Uani 1 1 d . . . N1 N 0.01839(13) 0.14864(13) 0.52950(2) 0.0153(3) Uani 1 1 d . . . N2 N -0.01674(13) 0.10198(13) 0.55147(2) 0.0152(3) Uani 1 1 d . . . C1 C 0.0000 0.0000 0.55930(5) 0.0153(6) Uani 1 3 d S . . H1 H 0.0000 0.0000 0.5759 0.018 Uiso 1 3 d SR . . C2 C -0.07394(16) 0.15535(16) 0.56303(3) 0.0181(4) Uani 1 1 d . . . C3 C -0.07436(16) 0.24079(16) 0.54803(3) 0.0194(4) Uani 1 1 d . . . H3 H -0.1073 0.2939 0.5509 0.023 Uiso 1 1 calc R . . C4 C -0.01608(15) 0.23382(15) 0.52754(3) 0.0170(4) Uani 1 1 d . . . C5 C -0.12127(18) 0.12421(17) 0.58749(3) 0.0240(4) Uani 1 1 d . . . H5A H -0.0509 0.1619 0.5986 0.029 Uiso 1 1 calc R . . H5B H -0.1766 0.1582 0.5908 0.029 Uiso 1 1 calc R . . C6 C -0.2431(3) -0.0392(2) 0.61289(4) 0.0538(7) Uani 1 1 d . . . H6A H -0.1785 -0.0051 0.6249 0.081 Uiso 1 1 calc R . . H6B H -0.2905 -0.1298 0.6142 0.081 Uiso 1 1 calc R . . H6C H -0.2990 -0.0057 0.6150 0.081 Uiso 1 1 calc R . . C7 C 0.00908(16) 0.30485(16) 0.50527(3) 0.0199(4) Uani 1 1 d . . . H7A H 0.0335 0.2655 0.4930 0.024 Uiso 1 1 calc R . . H7B H -0.0667 0.3049 0.5001 0.024 Uiso 1 1 calc R . . C8 C 0.13527(19) 0.50097(18) 0.48834(3) 0.0300(5) Uani 1 1 d . . . H8A H 0.1656 0.4661 0.4764 0.045 Uiso 1 1 calc R . . H8B H 0.1995 0.5866 0.4917 0.045 Uiso 1 1 calc R . . H8C H 0.0605 0.4998 0.4826 0.045 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 I1 0.03935(18) 0.03935(18) 0.0843(3) 0.000 0.000 0.01968(9) Na1 0.0158(5) 0.0158(5) 0.0136(8) 0.000 0.000 0.0079(2) O1 0.0564(10) 0.0256(8) 0.0352(8) 0.0056(6) 0.0290(7) 0.0162(7) O2 0.0241(7) 0.0164(7) 0.0332(7) 0.0039(5) -0.0040(6) 0.0061(6) N1 0.0148(7) 0.0133(7) 0.0151(7) 0.0004(6) -0.0003(6) 0.0050(6) N2 0.0164(7) 0.0151(7) 0.0141(7) -0.0010(6) 0.0008(6) 0.0079(6) C1 0.0162(9) 0.0162(9) 0.0136(13) 0.000 0.000 0.0081(4) C2 0.0134(9) 0.0174(9) 0.0220(9) -0.0051(7) -0.0008(7) 0.0065(7) C3 0.0181(9) 0.0167(9) 0.0249(9) -0.0050(7) -0.0017(7) 0.0099(8) C4 0.0143(9) 0.0130(9) 0.0218(9) -0.0033(7) -0.0041(7) 0.0054(7) C5 0.0269(10) 0.0233(10) 0.0222(9) -0.0037(8) 0.0044(8) 0.0129(8) C6 0.0754(19) 0.0455(15) 0.0421(13) 0.0163(11) 0.0389(13) 0.0312(14) C7 0.0209(10) 0.0153(9) 0.0252(10) 0.0002(7) -0.0017(7) 0.0103(8) C8 0.0267(11) 0.0221(10) 0.0421(12) 0.0108(9) 0.0087(9) 0.0129(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 Na1 N1 2.4301(13) 19_556 ? Na1 N1 2.4301(13) 21_556 ? Na1 N1 2.4301(14) 20_556 ? Na1 N1 2.4301(13) . ? Na1 N1 2.4301(13) 3 ? Na1 N1 2.4301(14) 2 ? O1 C5 1.406(2) . ? O1 C6 1.430(2) . ? O2 C8 1.424(2) . ? O2 C7 1.424(2) . ? N1 C4 1.332(2) . ? N1 N2 1.3630(18) . ? N2 C2 1.363(2) . ? N2 C1 1.4560(16) . ? C1 N2 1.4560(16) 2 ? C1 N2 1.4560(16) 3 ? C2 C3 1.369(2) . ? C2 C5 1.494(2) . ? C3 C4 1.405(2) . ? C4 C7 1.493(2) . ? 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 N1 Na1 N1 77.00(5) 19_556 21_556 ? N1 Na1 N1 77.00(5) 19_556 20_556 ? N1 Na1 N1 77.00(5) 21_556 20_556 ? N1 Na1 N1 180.00(4) 19_556 . ? N1 Na1 N1 103.00(5) 21_556 . ? N1 Na1 N1 103.00(5) 20_556 . ? N1 Na1 N1 103.00(5) 19_556 3 ? N1 Na1 N1 180.00(4) 21_556 3 ? N1 Na1 N1 103.00(5) 20_556 3 ? N1 Na1 N1 77.00(5) . 3 ? N1 Na1 N1 103.00(5) 19_556 2 ? N1 Na1 N1 103.00(5) 21_556 2 ? N1 Na1 N1 180.0 20_556 2 ? N1 Na1 N1 77.00(5) . 2 ? N1 Na1 N1 77.00(5) 3 2 ? C5 O1 C6 111.07(15) . . ? C8 O2 C7 111.31(14) . . ? C4 N1 N2 104.75(13) . . ? C4 N1 Na1 126.99(10) . . ? N2 N1 Na1 115.43(10) . . ? N1 N2 C2 112.02(13) . . ? N1 N2 C1 120.03(15) . . ? C2 N2 C1 127.76(15) . . ? N2 C1 N2 110.96(11) 2 3 ? N2 C1 N2 110.96(11) 2 . ? N2 C1 N2 110.96(11) 3 . ? N2 C2 C3 106.23(14) . . ? N2 C2 C5 124.27(16) . . ? C3 C2 C5 129.48(16) . . ? C2 C3 C4 105.88(15) . . ? N1 C4 C3 111.11(15) . . ? N1 C4 C7 119.19(15) . . ? C3 C4 C7 129.70(16) . . ? O1 C5 C2 109.46(14) . . ? O2 C7 C4 108.82(13) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.69 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.316 _refine_diff_density_min -0.429 _refine_diff_density_rms 0.046