# Supplementary Material (ESI) for New Journal of Chemistry # This journal is (c) The Royal Society of Chemistry and The Centre National de la Recherche Scientifique, 2011 data_publication_text _journal_name_full 'New J.Chem.' _journal_coden_cambridge 0440 _publ_contact_author_name 'Jonathan S. Lindsey' _publ_contact_author_address ;Department of Chemistry Campus Box 8204 Raleigh, NC 27695-8204 USA ; _publ_contact_author_email jlindsey@ncsu.edu _publ_contact_author_phone 919-515-6406 _publ_contact_author_fax 919-513-2830 loop_ _publ_author_name _publ_author_address K.Aravindu ;Department of Chemistry Campus Box 8204 Raleigh, NC 27695-8204 USA ; M.Krayer ;Department of Chemistry Campus Box 8204 Raleigh, NC 27695-8204 USA ; H.-J.Kim ;Department of Science Education Gongju National University of Education Gongju City, Korea ; J.S.Lindsey ;Department of Chemistry Campus Box 8204 Raleigh, NC 27695-8204 USA ; data_x05058 _database_code_depnum_ccdc_archive 'CCDC 809306' #TrackingRef 'TDC-T-rev--x05058.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C49 H62 N4 O2' _chemical_formula_weight 739.03 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/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 17.0127(9) _cell_length_b 9.5391(5) _cell_length_c 26.1916(13) _cell_angle_alpha 90.00 _cell_angle_beta 102.583(2) _cell_angle_gamma 90.00 _cell_volume 4148.4(4) _cell_formula_units_Z 4 _cell_measurement_temperature 110 _cell_measurement_reflns_used 9976 _cell_measurement_theta_min 2.28 _cell_measurement_theta_max 24.52 _exptl_crystal_description plate _exptl_crystal_colour red _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.183 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1600 _exptl_absorpt_coefficient_mu 0.072 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9732 _exptl_absorpt_correction_T_max 0.9986 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 110 _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-Nonius Kappa Axis X8 Apex2' _diffrn_measurement_method 'omega and phi scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 58925 _diffrn_reflns_av_R_equivalents 0.0641 _diffrn_reflns_av_sigmaI/netI 0.0620 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 2.28 _diffrn_reflns_theta_max 25.74 _reflns_number_total 7899 _reflns_number_gt 4805 _reflns_threshold_expression >2sigma(I) _computing_data_collection Apex2 _computing_cell_refinement SAINT _computing_data_reduction SAINT _computing_structure_solution XS _computing_structure_refinement XL _computing_molecular_graphics NRCVAX _computing_publication_material cif2tables.py _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^)+(0.1458P)^2^+6.5854P] 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 7899 _refine_ls_number_parameters 506 _refine_ls_number_restraints 133 _refine_ls_R_factor_all 0.1499 _refine_ls_R_factor_gt 0.0939 _refine_ls_wR_factor_ref 0.2866 _refine_ls_wR_factor_gt 0.2490 _refine_ls_goodness_of_fit_ref 1.061 _refine_ls_restrained_S_all 1.111 _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 0.24860(16) 0.0433(3) -0.00200(10) 0.0274(7) Uani 1 1 d . . . O2 O 0.38213(16) -0.0148(3) 0.00772(11) 0.0289(7) Uani 1 1 d . . . N20 N 0.37724(19) -0.1896(3) 0.09185(12) 0.0250(8) Uani 1 1 d . . . N21 N 0.4623(2) -0.3092(4) 0.18801(13) 0.0339(9) Uani 1 1 d . . . H21 H 0.4156 -0.2665 0.1778 0.041 Uiso 1 1 calc R . . N22 N 0.3379(2) -0.2075(4) 0.23792(13) 0.0300(8) Uani 1 1 d . . . N23 N 0.2573(2) -0.1382(3) 0.13782(12) 0.0266(8) Uani 1 1 d . . . H23 H 0.3067 -0.1486 0.1564 0.032 Uiso 1 1 calc R . . C1 C 0.3028(2) -0.1481(4) 0.05484(15) 0.0253(9) Uani 1 1 d . . . C2 C 0.2877(2) -0.2599(4) 0.01091(15) 0.0262(9) Uani 1 1 d . . . H2A H 0.2396 -0.3169 0.0124 0.031 Uiso 1 1 calc R . . H2B H 0.2794 -0.2149 -0.0239 0.031 Uiso 1 1 calc R . . C3 C 0.3642(3) -0.3521(4) 0.02112(16) 0.0283(9) Uani 1 1 d . . . C4 C 0.4106(2) -0.2938(4) 0.07288(15) 0.0264(9) Uani 1 1 d . . . C5 C 0.4865(3) -0.3537(4) 0.10170(17) 0.0315(10) Uani 1 1 d . . . H5 H 0.5218 -0.3941 0.0823 0.038 Uiso 1 1 calc R . . C6 C 0.5088(3) -0.3546(4) 0.15432(16) 0.0318(10) Uani 1 1 d . . . C7 C 0.5836(3) -0.4104(5) 0.18813(17) 0.0340(10) Uani 1 1 d . . . C8 C 0.5735(3) -0.4019(5) 0.23831(17) 0.0358(11) Uani 1 1 d . . . H8 H 0.6114 -0.4335 0.2683 0.043 Uiso 1 1 calc R . . C9 C 0.4972(3) -0.3383(5) 0.23941(16) 0.0347(10) Uani 1 1 d . . . C10 C 0.4645(3) -0.3110(5) 0.28158(17) 0.0343(10) Uani 1 1 d . . . H10 H 0.4959 -0.3364 0.3149 0.041 Uiso 1 1 calc R . . C11 C 0.3884(3) -0.2483(4) 0.28063(15) 0.0309(10) Uani 1 1 d . . . C12 C 0.3571(3) -0.2282(5) 0.32963(17) 0.0386(11) Uani 1 1 d . . . H12A H 0.3948 -0.1710 0.3556 0.046 Uiso 1 1 calc R . . H12B H 0.3487 -0.3195 0.3456 0.046 Uiso 1 1 calc R . . C13 C 0.2765(3) -0.1511(5) 0.31028(16) 0.0354(11) Uani 1 1 d . . . C14 C 0.2671(3) -0.1575(4) 0.25115(16) 0.0295(10) Uani 1 1 d . . . C15 C 0.2003(3) -0.1222(4) 0.21519(15) 0.0294(9) Uani 1 1 d . . . H15 H 0.1548 -0.0933 0.2281 0.035 Uiso 1 1 calc R . . C16 C 0.1913(3) -0.1242(4) 0.15896(15) 0.0273(9) Uani 1 1 d . . . C17 C 0.1254(2) -0.1068(4) 0.11734(15) 0.0272(9) Uani 1 1 d . . . C18 C 0.1557(2) -0.1122(4) 0.07059(16) 0.0293(9) Uani 1 1 d . . . H18 H 0.1247 -0.1024 0.0359 0.035 Uiso 1 1 calc R . . C19 C 0.2378(2) -0.1343(4) 0.08451(15) 0.0264(9) Uani 1 1 d . . . C20 C 0.3187(2) -0.0021(4) 0.03364(15) 0.0246(9) Uani 1 1 d . . . H20 H 0.3333 0.0663 0.0632 0.029 Uiso 1 1 calc R . . C21 C 0.2127(3) 0.1673(4) 0.01253(19) 0.0362(11) Uani 1 1 d . . . H21A H 0.1930 0.1497 0.0444 0.054 Uiso 1 1 calc R . . H21B H 0.1676 0.1949 -0.0158 0.054 Uiso 1 1 calc R . . H21C H 0.2528 0.2426 0.0190 0.054 Uiso 1 1 calc R . . C22 C 0.4061(3) 0.1163(4) -0.01059(19) 0.0368(11) Uani 1 1 d . . . H22A H 0.3609 0.1566 -0.0361 0.055 Uiso 1 1 calc R . . H22B H 0.4517 0.1014 -0.0272 0.055 Uiso 1 1 calc R . . H22C H 0.4219 0.1808 0.0190 0.055 Uiso 1 1 calc R . . C23 C 0.4109(3) -0.3399(5) -0.02274(17) 0.0333(10) Uani 1 1 d . . . H23A H 0.4214 -0.2408 -0.0287 0.050 Uiso 1 1 calc R . . H23B H 0.3789 -0.3808 -0.0550 0.050 Uiso 1 1 calc R . . H23C H 0.4622 -0.3902 -0.0125 0.050 Uiso 1 1 calc R . . C24 C 0.3440(3) -0.5063(4) 0.02853(19) 0.0406(11) Uani 1 1 d . . . H24A H 0.3940 -0.5608 0.0376 0.061 Uiso 1 1 calc R . . H24B H 0.3105 -0.5427 -0.0040 0.061 Uiso 1 1 calc R . . H24C H 0.3147 -0.5141 0.0567 0.061 Uiso 1 1 calc R . . C25 C 0.6553(3) -0.4564(5) 0.17082(17) 0.0366(11) Uani 1 1 d . . . C26 C 0.6849(3) -0.3815(5) 0.13348(18) 0.0397(11) Uani 1 1 d . . . H26 H 0.6558 -0.3025 0.1172 0.048 Uiso 1 1 calc R . . C27 C 0.7556(3) -0.4193(6) 0.11956(18) 0.0425(12) Uani 1 1 d . . . H27 H 0.7746 -0.3646 0.0945 0.051 Uiso 1 1 calc R . . C28 C 0.7995(3) -0.5349(6) 0.1412(2) 0.0530(14) Uani 1 1 d . . . C29 C 0.7697(4) -0.6103(7) 0.1784(3) 0.0688(18) Uani 1 1 d . . . H29 H 0.7987 -0.6899 0.1942 0.083 Uiso 1 1 calc R . . C30 C 0.6992(3) -0.5728(6) 0.1930(2) 0.0557(15) Uani 1 1 d . . . H30 H 0.6805 -0.6270 0.2184 0.067 Uiso 1 1 calc R . . C31 C 0.8766(4) -0.5756(8) 0.1264(3) 0.0758(19) Uani 1 1 d . . . H31A H 0.8647 -0.6152 0.0910 0.114 Uiso 1 1 calc R . . H31B H 0.9047 -0.6457 0.1511 0.114 Uiso 1 1 calc R . . H31C H 0.9108 -0.4926 0.1273 0.114 Uiso 1 1 calc R . . C32 C 0.0408(2) -0.0889(4) 0.12001(16) 0.0293(10) Uani 1 1 d . . . C33 C 0.0059(3) -0.1651(5) 0.15456(16) 0.0331(10) Uani 1 1 d . . . H33 H 0.0371 -0.2327 0.1768 0.040 Uiso 1 1 calc R . . C34 C -0.0744(3) -0.1437(5) 0.15718(17) 0.0368(11) Uani 1 1 d . . . H34 H -0.0965 -0.1975 0.1811 0.044 Uiso 1 1 calc R . . C35 C -0.1222(3) -0.0467(5) 0.12595(16) 0.0350(11) Uani 1 1 d . . . C36 C -0.0882(3) 0.0276(5) 0.09041(17) 0.0361(11) Uani 1 1 d . . . H36 H -0.1200 0.0939 0.0679 0.043 Uiso 1 1 calc R . . C37 C -0.0087(2) 0.0067(5) 0.08730(16) 0.0315(10) Uani 1 1 d . . . H37 H 0.0126 0.0584 0.0624 0.038 Uiso 1 1 calc R . . C38 C -0.2078(3) -0.0206(6) 0.12993(19) 0.0460(13) Uani 1 1 d . . . H38A H -0.2195 -0.0745 0.1592 0.069 Uiso 1 1 calc R . . H38B H -0.2443 -0.0497 0.0974 0.069 Uiso 1 1 calc R . . H38C H -0.2153 0.0796 0.1358 0.069 Uiso 1 1 calc R . . C39 C 0.2832(4) 0.0030(6) 0.3281(2) 0.0636(18) Uani 1 1 d . . . H39A H 0.2340 0.0533 0.3114 0.095 Uiso 1 1 calc R . . H39B H 0.3297 0.0465 0.3179 0.095 Uiso 1 1 calc R . . H39C H 0.2900 0.0074 0.3662 0.095 Uiso 1 1 calc R . . C40 C 0.2073(4) -0.2232(8) 0.3282(2) 0.0724(19) Uani 1 1 d . . . H40A H 0.1572 -0.1717 0.3147 0.109 Uiso 1 1 calc R . . H40B H 0.2184 -0.2247 0.3665 0.109 Uiso 1 1 calc R . . H40C H 0.2018 -0.3194 0.3148 0.109 Uiso 1 1 calc R . . C1S C 0.4941(3) 0.2112(4) 0.14476(17) 0.0431(12) Uani 1 1 d DU . . H1S1 H 0.4418 0.1652 0.1304 0.052 Uiso 1 1 calc R . . H1S2 H 0.4917 0.3081 0.1310 0.052 Uiso 1 1 calc R . . C2S C 0.5586(5) 0.1342(8) 0.1285(3) 0.122(3) Uani 1 1 d DU . . H2S1 H 0.6079 0.1928 0.1362 0.146 Uiso 1 1 calc R . . H2S2 H 0.5435 0.1210 0.0902 0.146 Uiso 1 1 calc R . . C3S C 0.5781(5) -0.0028(6) 0.1530(3) 0.116(3) Uani 1 1 d DU . . H3S1 H 0.5330 -0.0682 0.1399 0.139 Uiso 1 1 calc R . . H3S2 H 0.6266 -0.0404 0.1426 0.139 Uiso 1 1 calc R . . C4S C 0.5928(4) 0.0034(5) 0.2098(2) 0.099(2) Uani 1 1 d DU . . H4S1 H 0.6427 0.0573 0.2234 0.119 Uiso 1 1 calc R . . H4S2 H 0.6006 -0.0927 0.2243 0.119 Uiso 1 1 calc R . . C5S C 0.5233(5) 0.0720(7) 0.2273(2) 0.113(2) Uani 1 1 d DU . . H5S1 H 0.4741 0.0144 0.2162 0.136 Uiso 1 1 calc R . . H5S2 H 0.5354 0.0791 0.2659 0.136 Uiso 1 1 calc R . . C6S C 0.5093(6) 0.2146(7) 0.2039(2) 0.119(3) Uani 1 1 d DU . . H6S1 H 0.5570 0.2739 0.2176 0.143 Uiso 1 1 calc R . . H6S2 H 0.4624 0.2576 0.2145 0.143 Uiso 1 1 calc R . . C7S C 0.4541(3) 0.0546(5) 0.45042(19) 0.0639(17) Uani 1 1 d DU . . H7S1 H 0.4106 0.1170 0.4321 0.077 Uiso 1 1 calc R . . H7S2 H 0.4794 0.0103 0.4238 0.077 Uiso 1 1 calc R . . C8S C 0.4196(3) -0.0554(5) 0.4789(2) 0.0591(15) Uani 1 1 d DU . . H8S1 H 0.3849 -0.1182 0.4534 0.071 Uiso 1 1 calc R . . H8S2 H 0.3857 -0.0111 0.5006 0.071 Uiso 1 1 calc R . . C9S C 0.4844(4) -0.1392(6) 0.5129(3) 0.129(4) Uani 1 1 d DU . . H9S1 H 0.5121 -0.1952 0.4903 0.155 Uiso 1 1 calc R . . H9S2 H 0.4592 -0.2056 0.5336 0.155 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 O1 0.0302(15) 0.0214(15) 0.0275(15) -0.0007(11) -0.0008(12) 0.0047(12) O2 0.0308(16) 0.0167(14) 0.0392(16) 0.0028(12) 0.0075(13) -0.0001(12) N20 0.0270(18) 0.0200(18) 0.0252(17) -0.0003(14) -0.0001(14) 0.0010(14) N21 0.034(2) 0.034(2) 0.0310(19) 0.0050(16) 0.0010(16) 0.0099(16) N22 0.035(2) 0.0224(18) 0.0294(19) 0.0002(15) 0.0011(16) 0.0009(15) N23 0.0290(19) 0.0231(18) 0.0246(18) -0.0009(14) -0.0009(14) 0.0030(14) C1 0.027(2) 0.021(2) 0.024(2) -0.0023(17) -0.0020(16) 0.0014(17) C2 0.026(2) 0.021(2) 0.029(2) -0.0029(17) 0.0007(17) -0.0027(17) C3 0.037(2) 0.017(2) 0.029(2) -0.0006(17) 0.0043(18) 0.0001(17) C4 0.033(2) 0.020(2) 0.026(2) 0.0031(17) 0.0048(17) -0.0015(18) C5 0.029(2) 0.025(2) 0.038(2) 0.0003(19) 0.0016(19) 0.0043(18) C6 0.033(2) 0.027(2) 0.033(2) 0.0064(19) 0.0004(19) 0.0052(19) C7 0.037(2) 0.029(2) 0.033(2) 0.0042(19) -0.0009(19) 0.0044(19) C8 0.035(2) 0.031(2) 0.034(2) 0.0040(19) -0.0073(19) 0.007(2) C9 0.043(3) 0.027(2) 0.029(2) 0.0038(18) -0.004(2) 0.005(2) C10 0.040(3) 0.030(2) 0.029(2) 0.0032(19) -0.0013(19) 0.001(2) C11 0.042(3) 0.022(2) 0.025(2) 0.0023(17) -0.0024(19) -0.0017(19) C12 0.050(3) 0.035(3) 0.027(2) 0.0028(19) -0.001(2) 0.010(2) C13 0.050(3) 0.026(2) 0.027(2) -0.0013(18) 0.002(2) 0.005(2) C14 0.039(3) 0.020(2) 0.028(2) -0.0010(17) 0.0046(19) 0.0000(18) C15 0.036(2) 0.024(2) 0.027(2) -0.0008(17) 0.0050(18) 0.0037(18) C16 0.034(2) 0.020(2) 0.026(2) -0.0015(17) 0.0039(18) 0.0042(17) C17 0.032(2) 0.021(2) 0.027(2) -0.0014(17) 0.0020(18) -0.0008(17) C18 0.028(2) 0.031(2) 0.026(2) -0.0003(18) -0.0016(17) -0.0006(18) C19 0.032(2) 0.020(2) 0.024(2) 0.0008(16) 0.0001(17) -0.0003(17) C20 0.026(2) 0.019(2) 0.026(2) -0.0018(16) 0.0006(17) 0.0012(16) C21 0.036(2) 0.020(2) 0.049(3) -0.001(2) 0.002(2) 0.0073(19) C22 0.038(2) 0.020(2) 0.054(3) 0.006(2) 0.011(2) -0.0039(19) C23 0.034(2) 0.029(2) 0.036(2) -0.0011(19) 0.0058(19) 0.0044(19) C24 0.052(3) 0.018(2) 0.048(3) -0.001(2) 0.004(2) -0.003(2) C25 0.035(2) 0.033(2) 0.037(2) 0.001(2) -0.003(2) 0.010(2) C26 0.037(3) 0.039(3) 0.037(3) 0.001(2) -0.005(2) 0.011(2) C27 0.036(3) 0.052(3) 0.036(3) -0.006(2) 0.000(2) 0.003(2) C28 0.040(3) 0.063(4) 0.052(3) -0.010(3) 0.000(2) 0.013(3) C29 0.065(4) 0.056(4) 0.080(4) 0.015(3) 0.006(3) 0.034(3) C30 0.057(3) 0.050(3) 0.059(3) 0.020(3) 0.012(3) 0.025(3) C31 0.054(4) 0.092(5) 0.080(4) -0.008(4) 0.013(3) 0.030(4) C32 0.032(2) 0.027(2) 0.027(2) -0.0083(18) 0.0039(18) -0.0014(18) C33 0.038(3) 0.031(2) 0.028(2) -0.0040(19) 0.0042(19) 0.001(2) C34 0.039(3) 0.041(3) 0.032(2) -0.010(2) 0.010(2) -0.008(2) C35 0.032(2) 0.044(3) 0.026(2) -0.014(2) 0.0013(18) -0.003(2) C36 0.033(2) 0.043(3) 0.029(2) -0.004(2) -0.0016(19) 0.004(2) C37 0.030(2) 0.037(2) 0.026(2) -0.0036(19) 0.0011(18) -0.0030(19) C38 0.032(3) 0.064(3) 0.041(3) -0.012(2) 0.006(2) -0.002(2) C39 0.103(5) 0.041(3) 0.034(3) -0.011(2) -0.014(3) 0.027(3) C40 0.063(4) 0.117(6) 0.035(3) 0.022(3) 0.007(3) -0.005(4) C1S 0.045(3) 0.018(2) 0.055(3) -0.014(2) -0.014(2) 0.0045(19) C2S 0.170(7) 0.109(6) 0.098(5) -0.010(4) 0.052(5) 0.009(6) C3S 0.121(6) 0.061(4) 0.174(6) -0.035(5) 0.052(6) 0.019(4) C4S 0.086(4) 0.020(3) 0.140(5) -0.003(3) -0.085(4) 0.002(3) C5S 0.171(7) 0.097(5) 0.072(4) -0.007(4) 0.026(5) -0.047(5) C6S 0.130(7) 0.112(5) 0.115(5) -0.024(5) 0.025(5) 0.044(5) C7S 0.059(3) 0.055(3) 0.061(3) 0.025(3) -0.023(3) -0.027(3) C8S 0.045(3) 0.072(4) 0.052(3) 0.015(3) -0.007(2) -0.027(3) C9S 0.129(6) 0.071(5) 0.132(6) 0.070(4) -0.091(5) -0.069(4) _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 C20 1.413(5) . ? O1 C21 1.420(5) . ? O2 C20 1.399(5) . ? O2 C22 1.430(5) . ? N20 C4 1.296(5) . ? N20 C1 1.471(5) . ? N21 C9 1.376(5) . ? N21 C6 1.378(6) . ? N21 H21 0.8800 . ? N22 C11 1.312(5) . ? N22 C14 1.407(5) . ? N23 C16 1.362(5) . ? N23 C19 1.363(5) . ? N23 H23 0.8800 . ? C1 C19 1.490(6) . ? C1 C20 1.546(5) . ? C1 C2 1.549(5) . ? C2 C3 1.544(6) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.518(6) . ? C3 C24 1.532(6) . ? C3 C23 1.537(6) . ? C4 C5 1.462(6) . ? C5 C6 1.347(6) . ? C5 H5 0.9500 . ? C6 C7 1.482(6) . ? C7 C8 1.364(6) . ? C7 C25 1.459(6) . ? C8 C9 1.439(6) . ? C8 H8 0.9500 . ? C9 C10 1.365(6) . ? C10 C11 1.423(6) . ? C10 H10 0.9500 . ? C11 C12 1.505(6) . ? C12 C13 1.541(6) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C40 1.522(7) . ? C13 C14 1.523(6) . ? C13 C39 1.539(7) . ? C14 C15 1.351(6) . ? C15 C16 1.447(6) . ? C15 H15 0.9500 . ? C16 C17 1.393(6) . ? C17 C18 1.429(6) . ? C17 C32 1.466(6) . ? C18 C19 1.380(6) . ? C18 H18 0.9500 . ? C20 H20 1.0000 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C25 C26 1.392(7) . ? C25 C30 1.392(7) . ? C26 C27 1.378(7) . ? C26 H26 0.9500 . ? C27 C28 1.382(7) . ? C27 H27 0.9500 . ? C28 C29 1.391(9) . ? C28 C31 1.498(8) . ? C29 C30 1.384(8) . ? C29 H29 0.9500 . ? C30 H30 0.9500 . ? C31 H31A 0.9800 . ? C31 H31B 0.9800 . ? C31 H31C 0.9800 . ? C32 C33 1.391(6) . ? C32 C37 1.401(6) . ? C33 C34 1.397(6) . ? C33 H33 0.9500 . ? C34 C35 1.377(7) . ? C34 H34 0.9500 . ? C35 C36 1.392(6) . ? C35 C38 1.504(6) . ? C36 C37 1.386(6) . ? C36 H36 0.9500 . ? C37 H37 0.9500 . ? C38 H38A 0.9800 . ? C38 H38B 0.9800 . ? C38 H38C 0.9800 . ? C39 H39A 0.9800 . ? C39 H39B 0.9800 . ? C39 H39C 0.9800 . ? C40 H40A 0.9800 . ? C40 H40B 0.9800 . ? C40 H40C 0.9800 . ? C1S C2S 1.459(5) . ? C1S C6S 1.513(5) . ? C1S H1S1 0.9900 . ? C1S H1S2 0.9900 . ? C2S C3S 1.462(5) . ? C2S H2S1 0.9900 . ? C2S H2S2 0.9900 . ? C3S C4S 1.456(5) . ? C3S H3S1 0.9900 . ? C3S H3S2 0.9900 . ? C4S C5S 1.508(5) . ? C4S H4S1 0.9900 . ? C4S H4S2 0.9900 . ? C5S C6S 1.490(5) . ? C5S H5S1 0.9900 . ? C5S H5S2 0.9900 . ? C6S H6S1 0.9900 . ? C6S H6S2 0.9900 . ? C7S C8S 1.480(5) . ? C7S C9S 1.494(5) 3_656 ? C7S H7S1 0.9900 . ? C7S H7S2 0.9900 . ? C8S C9S 1.489(5) . ? C8S H8S1 0.9900 . ? C8S H8S2 0.9900 . ? C9S C7S 1.494(5) 3_656 ? C9S H9S1 0.9900 . ? C9S H9S2 0.9900 . ? 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 C20 O1 C21 115.3(3) . . ? C20 O2 C22 113.1(3) . . ? C4 N20 C1 109.9(3) . . ? C9 N21 C6 112.2(4) . . ? C9 N21 H21 123.9 . . ? C6 N21 H21 123.9 . . ? C11 N22 C14 109.1(3) . . ? C16 N23 C19 112.1(3) . . ? C16 N23 H23 124.0 . . ? C19 N23 H23 124.0 . . ? N20 C1 C19 108.1(3) . . ? N20 C1 C20 106.6(3) . . ? C19 C1 C20 108.4(3) . . ? N20 C1 C2 106.5(3) . . ? C19 C1 C2 115.3(3) . . ? C20 C1 C2 111.6(3) . . ? C3 C2 C1 105.5(3) . . ? C3 C2 H2A 110.6 . . ? C1 C2 H2A 110.6 . . ? C3 C2 H2B 110.6 . . ? C1 C2 H2B 110.6 . . ? H2A C2 H2B 108.8 . . ? C4 C3 C24 109.0(3) . . ? C4 C3 C23 112.7(3) . . ? C24 C3 C23 109.5(3) . . ? C4 C3 C2 101.6(3) . . ? C24 C3 C2 111.4(4) . . ? C23 C3 C2 112.3(3) . . ? N20 C4 C5 120.9(4) . . ? N20 C4 C3 115.9(4) . . ? C5 C4 C3 123.1(4) . . ? C6 C5 C4 123.5(4) . . ? C6 C5 H5 118.3 . . ? C4 C5 H5 118.3 . . ? C5 C6 N21 125.4(4) . . ? C5 C6 C7 128.9(4) . . ? N21 C6 C7 105.6(3) . . ? C8 C7 C25 127.4(4) . . ? C8 C7 C6 106.4(4) . . ? C25 C7 C6 126.1(4) . . ? C7 C8 C9 110.4(4) . . ? C7 C8 H8 124.8 . . ? C9 C8 H8 124.8 . . ? C10 C9 N21 126.0(4) . . ? C10 C9 C8 128.6(4) . . ? N21 C9 C8 105.3(4) . . ? C9 C10 C11 126.6(4) . . ? C9 C10 H10 116.7 . . ? C11 C10 H10 116.7 . . ? N22 C11 C10 124.3(4) . . ? N22 C11 C12 113.7(4) . . ? C10 C11 C12 121.9(4) . . ? C11 C12 C13 103.6(3) . . ? C11 C12 H12A 111.0 . . ? C13 C12 H12A 111.0 . . ? C11 C12 H12B 111.0 . . ? C13 C12 H12B 111.0 . . ? H12A C12 H12B 109.0 . . ? C40 C13 C14 112.2(4) . . ? C40 C13 C39 110.4(5) . . ? C14 C13 C39 109.3(4) . . ? C40 C13 C12 112.1(4) . . ? C14 C13 C12 101.8(3) . . ? C39 C13 C12 110.8(4) . . ? C15 C14 N22 123.2(4) . . ? C15 C14 C13 125.8(4) . . ? N22 C14 C13 111.0(4) . . ? C14 C15 C16 126.4(4) . . ? C14 C15 H15 116.8 . . ? C16 C15 H15 116.8 . . ? N23 C16 C17 106.7(3) . . ? N23 C16 C15 120.1(4) . . ? C17 C16 C15 133.1(4) . . ? C16 C17 C18 106.7(4) . . ? C16 C17 C32 127.4(4) . . ? C18 C17 C32 125.9(4) . . ? C19 C18 C17 108.2(4) . . ? C19 C18 H18 125.9 . . ? C17 C18 H18 125.9 . . ? N23 C19 C18 106.3(4) . . ? N23 C19 C1 119.3(3) . . ? C18 C19 C1 134.4(4) . . ? O2 C20 O1 109.6(3) . . ? O2 C20 C1 108.1(3) . . ? O1 C20 C1 108.9(3) . . ? O2 C20 H20 110.1 . . ? O1 C20 H20 110.1 . . ? C1 C20 H20 110.1 . . ? O1 C21 H21A 109.5 . . ? O1 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? O1 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? O2 C22 H22A 109.5 . . ? O2 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? O2 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C3 C23 H23A 109.5 . . ? C3 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C3 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C3 C24 H24A 109.5 . . ? C3 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C3 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C26 C25 C30 117.3(4) . . ? C26 C25 C7 121.3(4) . . ? C30 C25 C7 121.3(4) . . ? C27 C26 C25 121.5(4) . . ? C27 C26 H26 119.3 . . ? C25 C26 H26 119.3 . . ? C26 C27 C28 121.7(5) . . ? C26 C27 H27 119.2 . . ? C28 C27 H27 119.2 . . ? C27 C28 C29 116.9(5) . . ? C27 C28 C31 121.7(6) . . ? C29 C28 C31 121.4(5) . . ? C30 C29 C28 122.0(5) . . ? C30 C29 H29 119.0 . . ? C28 C29 H29 119.0 . . ? C29 C30 C25 120.6(5) . . ? C29 C30 H30 119.7 . . ? C25 C30 H30 119.7 . . ? C28 C31 H31A 109.5 . . ? C28 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? C28 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? C33 C32 C37 116.9(4) . . ? C33 C32 C17 122.2(4) . . ? C37 C32 C17 120.9(4) . . ? C32 C33 C34 121.1(4) . . ? C32 C33 H33 119.4 . . ? C34 C33 H33 119.4 . . ? C35 C34 C33 121.7(4) . . ? C35 C34 H34 119.1 . . ? C33 C34 H34 119.1 . . ? C34 C35 C36 117.5(4) . . ? C34 C35 C38 121.7(4) . . ? C36 C35 C38 120.8(4) . . ? C37 C36 C35 121.2(4) . . ? C37 C36 H36 119.4 . . ? C35 C36 H36 119.4 . . ? C36 C37 C32 121.5(4) . . ? C36 C37 H37 119.2 . . ? C32 C37 H37 119.2 . . ? C35 C38 H38A 109.5 . . ? C35 C38 H38B 109.5 . . ? H38A C38 H38B 109.5 . . ? C35 C38 H38C 109.5 . . ? H38A C38 H38C 109.5 . . ? H38B C38 H38C 109.5 . . ? C13 C39 H39A 109.5 . . ? C13 C39 H39B 109.5 . . ? H39A C39 H39B 109.5 . . ? C13 C39 H39C 109.5 . . ? H39A C39 H39C 109.5 . . ? H39B C39 H39C 109.5 . . ? C13 C40 H40A 109.5 . . ? C13 C40 H40B 109.5 . . ? H40A C40 H40B 109.5 . . ? C13 C40 H40C 109.5 . . ? H40A C40 H40C 109.5 . . ? H40B C40 H40C 109.5 . . ? C2S C1S C6S 109.7(5) . . ? C2S C1S H1S1 109.7 . . ? C6S C1S H1S1 109.7 . . ? C2S C1S H1S2 109.7 . . ? C6S C1S H1S2 109.7 . . ? H1S1 C1S H1S2 108.2 . . ? C1S C2S C3S 115.8(5) . . ? C1S C2S H2S1 108.3 . . ? C3S C2S H2S1 108.3 . . ? C1S C2S H2S2 108.3 . . ? C3S C2S H2S2 108.3 . . ? H2S1 C2S H2S2 107.4 . . ? C4S C3S C2S 112.5(4) . . ? C4S C3S H3S1 109.1 . . ? C2S C3S H3S1 109.1 . . ? C4S C3S H3S2 109.1 . . ? C2S C3S H3S2 109.1 . . ? H3S1 C3S H3S2 107.8 . . ? C3S C4S C5S 110.9(4) . . ? C3S C4S H4S1 109.5 . . ? C5S C4S H4S1 109.5 . . ? C3S C4S H4S2 109.5 . . ? C5S C4S H4S2 109.5 . . ? H4S1 C4S H4S2 108.0 . . ? C6S C5S C4S 109.6(4) . . ? C6S C5S H5S1 109.7 . . ? C4S C5S H5S1 109.7 . . ? C6S C5S H5S2 109.7 . . ? C4S C5S H5S2 109.7 . . ? H5S1 C5S H5S2 108.2 . . ? C5S C6S C1S 112.2(4) . . ? C5S C6S H6S1 109.2 . . ? C1S C6S H6S1 109.2 . . ? C5S C6S H6S2 109.2 . . ? C1S C6S H6S2 109.2 . . ? H6S1 C6S H6S2 107.9 . . ? C8S C7S C9S 111.0(4) . 3_656 ? C8S C7S H7S1 109.4 . . ? C9S C7S H7S1 109.4 3_656 . ? C8S C7S H7S2 109.4 . . ? C9S C7S H7S2 109.4 3_656 . ? H7S1 C7S H7S2 108.0 . . ? C7S C8S C9S 111.0(4) . . ? C7S C8S H8S1 109.4 . . ? C9S C8S H8S1 109.4 . . ? C7S C8S H8S2 109.4 . . ? C9S C8S H8S2 109.4 . . ? H8S1 C8S H8S2 108.0 . . ? C8S C9S C7S 114.7(5) . 3_656 ? C8S C9S H9S1 108.6 . . ? C7S C9S H9S1 108.6 3_656 . ? C8S C9S H9S2 108.6 . . ? C7S C9S H9S2 108.6 3_656 . ? H9S1 C9S H9S2 107.6 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C4 N20 C1 C19 132.1(3) . . . . ? C4 N20 C1 C20 -111.5(4) . . . . ? C4 N20 C1 C2 7.7(4) . . . . ? N20 C1 C2 C3 -8.4(4) . . . . ? C19 C1 C2 C3 -128.2(3) . . . . ? C20 C1 C2 C3 107.6(4) . . . . ? C1 C2 C3 C4 6.0(4) . . . . ? C1 C2 C3 C24 122.0(4) . . . . ? C1 C2 C3 C23 -114.7(4) . . . . ? C1 N20 C4 C5 179.0(4) . . . . ? C1 N20 C4 C3 -3.9(5) . . . . ? C24 C3 C4 N20 -119.3(4) . . . . ? C23 C3 C4 N20 118.9(4) . . . . ? C2 C3 C4 N20 -1.6(4) . . . . ? C24 C3 C4 C5 57.8(5) . . . . ? C23 C3 C4 C5 -64.1(5) . . . . ? C2 C3 C4 C5 175.5(4) . . . . ? N20 C4 C5 C6 29.9(6) . . . . ? C3 C4 C5 C6 -146.9(4) . . . . ? C4 C5 C6 N21 4.7(7) . . . . ? C4 C5 C6 C7 -179.5(4) . . . . ? C9 N21 C6 C5 172.8(4) . . . . ? C9 N21 C6 C7 -3.9(5) . . . . ? C5 C6 C7 C8 -172.8(5) . . . . ? N21 C6 C7 C8 3.7(5) . . . . ? C5 C6 C7 C25 10.8(8) . . . . ? N21 C6 C7 C25 -172.8(4) . . . . ? C25 C7 C8 C9 174.1(4) . . . . ? C6 C7 C8 C9 -2.3(5) . . . . ? C6 N21 C9 C10 -177.5(4) . . . . ? C6 N21 C9 C8 2.5(5) . . . . ? C7 C8 C9 C10 -180.0(5) . . . . ? C7 C8 C9 N21 0.0(5) . . . . ? N21 C9 C10 C11 0.4(8) . . . . ? C8 C9 C10 C11 -179.6(4) . . . . ? C14 N22 C11 C10 176.9(4) . . . . ? C14 N22 C11 C12 -0.8(5) . . . . ? C9 C10 C11 N22 0.1(7) . . . . ? C9 C10 C11 C12 177.6(4) . . . . ? N22 C11 C12 C13 -5.1(5) . . . . ? C10 C11 C12 C13 177.1(4) . . . . ? C11 C12 C13 C40 128.2(4) . . . . ? C11 C12 C13 C14 8.1(4) . . . . ? C11 C12 C13 C39 -107.9(4) . . . . ? C11 N22 C14 C15 -172.5(4) . . . . ? C11 N22 C14 C13 6.7(5) . . . . ? C40 C13 C14 C15 49.9(6) . . . . ? C39 C13 C14 C15 -73.0(6) . . . . ? C12 C13 C14 C15 169.9(4) . . . . ? C40 C13 C14 N22 -129.3(5) . . . . ? C39 C13 C14 N22 107.8(5) . . . . ? C12 C13 C14 N22 -9.4(5) . . . . ? N22 C14 C15 C16 -2.6(7) . . . . ? C13 C14 C15 C16 178.2(4) . . . . ? C19 N23 C16 C17 -1.4(5) . . . . ? C19 N23 C16 C15 -178.4(4) . . . . ? C14 C15 C16 N23 -12.5(6) . . . . ? C14 C15 C16 C17 171.5(4) . . . . ? N23 C16 C17 C18 0.4(4) . . . . ? C15 C16 C17 C18 176.8(4) . . . . ? N23 C16 C17 C32 179.3(4) . . . . ? C15 C16 C17 C32 -4.2(8) . . . . ? C16 C17 C18 C19 0.8(5) . . . . ? C32 C17 C18 C19 -178.2(4) . . . . ? C16 N23 C19 C18 1.9(5) . . . . ? C16 N23 C19 C1 180.0(3) . . . . ? C17 C18 C19 N23 -1.6(4) . . . . ? C17 C18 C19 C1 -179.2(4) . . . . ? N20 C1 C19 N23 10.1(5) . . . . ? C20 C1 C19 N23 -105.1(4) . . . . ? C2 C1 C19 N23 129.1(4) . . . . ? N20 C1 C19 C18 -172.5(4) . . . . ? C20 C1 C19 C18 72.3(6) . . . . ? C2 C1 C19 C18 -53.5(6) . . . . ? C22 O2 C20 O1 65.5(4) . . . . ? C22 O2 C20 C1 -176.0(3) . . . . ? C21 O1 C20 O2 -124.3(3) . . . . ? C21 O1 C20 C1 117.6(4) . . . . ? N20 C1 C20 O2 61.4(4) . . . . ? C19 C1 C20 O2 177.6(3) . . . . ? C2 C1 C20 O2 -54.5(4) . . . . ? N20 C1 C20 O1 -179.6(3) . . . . ? C19 C1 C20 O1 -63.5(4) . . . . ? C2 C1 C20 O1 64.5(4) . . . . ? C8 C7 C25 C26 -134.1(5) . . . . ? C6 C7 C25 C26 41.7(7) . . . . ? C8 C7 C25 C30 42.5(7) . . . . ? C6 C7 C25 C30 -141.8(5) . . . . ? C30 C25 C26 C27 -1.1(7) . . . . ? C7 C25 C26 C27 175.6(4) . . . . ? C25 C26 C27 C28 1.3(7) . . . . ? C26 C27 C28 C29 -1.0(8) . . . . ? C26 C27 C28 C31 -179.6(5) . . . . ? C27 C28 C29 C30 0.5(9) . . . . ? C31 C28 C29 C30 179.1(6) . . . . ? C28 C29 C30 C25 -0.3(10) . . . . ? C26 C25 C30 C29 0.6(8) . . . . ? C7 C25 C30 C29 -176.1(5) . . . . ? C16 C17 C32 C33 -40.6(6) . . . . ? C18 C17 C32 C33 138.2(4) . . . . ? C16 C17 C32 C37 139.6(4) . . . . ? C18 C17 C32 C37 -41.7(6) . . . . ? C37 C32 C33 C34 -1.6(6) . . . . ? C17 C32 C33 C34 178.5(4) . . . . ? C32 C33 C34 C35 -0.1(6) . . . . ? C33 C34 C35 C36 1.6(6) . . . . ? C33 C34 C35 C38 -178.1(4) . . . . ? C34 C35 C36 C37 -1.2(6) . . . . ? C38 C35 C36 C37 178.5(4) . . . . ? C35 C36 C37 C32 -0.6(6) . . . . ? C33 C32 C37 C36 2.0(6) . . . . ? C17 C32 C37 C36 -178.1(4) . . . . ? C6S C1S C2S C3S 49.8(10) . . . . ? C1S C2S C3S C4S -51.9(11) . . . . ? C2S C3S C4S C5S 53.8(9) . . . . ? C3S C4S C5S C6S -56.9(8) . . . . ? C4S C5S C6S C1S 56.9(9) . . . . ? C2S C1S C6S C5S -52.6(9) . . . . ? C9S C7S C8S C9S -51.2(9) 3_656 . . . ? C7S C8S C9S C7S 53.2(9) . . . 3_656 ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.74 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 1.597 _refine_diff_density_min -1.024 _refine_diff_density_rms 0.080