# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2002 data_global _journal_coden_Cambridge 182 loop_ _publ_author_name _publ_author_address 'Darren W. Johnson' ; Skaggs Institute for Chemical Biology (MB26) The Scripps Research Institute 10550 N. Torrey Pines Road La Jolla, CA 92037 ; 'Liam C. Palmer' ; Skaggs Institute for Chemical Biology (MB26) The Scripps Research Institute 10550 N. Torrey Pines Road La Jolla, CA 92037 ; 'Fraser Hof' ; Skaggs Institute for Chemical Biology (MB26) The Scripps Research Institute 10550 N. Torrey Pines Road La Jolla, CA 92037 ; 'Peter M. Iovine' ; Skaggs Institute for Chemical Biology (MB26) The Scripps Research Institute 10550 N. Torrey Pines Road La Jolla, CA 92037 ; 'Julius Rebek, Jr.' ; Skaggs Institute for Chemical Biology (MB26) The Scripps Research Institute 10550 N. Torrey Pines Road La Jolla, CA 92037 ; _publ_contact_author_name 'Prof Julius Rebek, Jr.' _publ_contact_author_address ; The Skaggs Institute for Chemical Biology The Scripps Research Institute 10550 North Torrey Pines Rd MB26 La Jolla CA 92037 UNITED STATES OF AMERICA ; _publ_contact_author_phone '858-784-2250' _publ_contact_author_fax '858-784-2876' _publ_contact_author_email 'jrebek@scripps.edu' _publ_requested_journal ; Chemical Communications ; _publ_section_title ; New Supramolecular Organization for Glycoluril: Chiral Hydrogen-Bonded Ribbons ; _publ_section_references ; Altomare, A., Burla, M. C., Camalli, M., Cascarano, M., Giacovazzo, C., Guagliardi, A., Polidori, G. (1993). J. Appl. Cryst., 26, 343-350. Siemens Industrial Automation, Inc. (1995). SMART. Area Detector Software Package, Madison, WI, USA. Siemens Industrial Automation, Inc. (1995). SAINT. SAX Area Detector Integration Program (v. 4.024), Madison, WI, USA. Siemens Industrial Automation, Inc. (1993). SHELXL. SHELXTL Crystal Structure Determination Software Package, Madison, WI, USA. ; data_meglys _database_code_CSD 184670 _audit_creation_method SHELXL-97 _computing_data_collection 'SMART (Siemens, 1995)' _computing_cell_refinement ; SMART (Siemens, 1995), SAINT (Siemens, 1995) ; _computing_data_reduction ; SAINT (Siemens, 1995), XPREP (Siemens, 1995) ; _computing_structure_solution 'SIR92 (Altomare, 1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #------------------------------------------------------------------------------ _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/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 15.6238(3) _cell_length_b 10.8061(2) _cell_length_c 18.8578(4) _cell_angle_alpha 90.00 _cell_angle_beta 111.2290(10) _cell_angle_gamma 90.00 _cell_volume 2967.75(10) _cell_formula_units_Z 4 _cell_measurement_temperature 119(2) _cell_measurement_reflns_used 7125 _cell_measurement_theta_min 3.033 _cell_measurement_theta_max 56.416 #------------------------------------------------------------------------------ _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.259 _exptl_crystal_F_000 1192 _chemical_compound_source 'synthetic' _exptl_absorpt_coefficient_mu 0.672 _chemical_formula_sum 'C34 H34 N4 O4' _chemical_formula_weight 562.65 _exptl_absorpt_correction_type 'psi-scan' _exptl_absorpt_correction_T_min 0.31448 _exptl_absorpt_correction_T_max 0.94914 _exptl_special_details ; ? ; #------------------------------------------------------------------------------ _diffrn_ambient_temperature 119(2) _diffrn_radiation_wavelength 1.54180 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'X-ray tube' _diffrn_radiation_monochromator 'mirror optics' _diffrn_radiation_detector 'CCD area detector' _diffrn_measurement_device_type '3 circle diffractometer' _diffrn_measurement_method ; omega scans with profile analysis ; _diffrn_reflns_number 9856 _diffrn_reflns_av_R_equivalents 0.0347 _diffrn_reflns_av_sigmaI/netI 0.0247 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.16 _diffrn_reflns_theta_max 56.41 _reflns_number_total 3549 _reflns_number_gt 3260 _reflns_threshold_expression >2sigma(I) _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^)+(0.1033P)^2^+1.9287P] 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 3549 _refine_ls_number_parameters 379 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0589 _refine_ls_R_factor_gt 0.0559 _refine_ls_wR_factor_ref 0.1570 _refine_ls_wR_factor_gt 0.1539 _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_restrained_S_all 1.036 _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 0.75104(12) 0.30691(17) 0.15766(9) 0.0385(5) Uani 1 1 d . . . O2 O 0.75538(12) -0.22451(17) 0.15667(9) 0.0373(5) Uani 1 1 d . . . O3 O 1.12606(14) -0.50359(19) 0.11158(11) 0.0487(6) Uani 1 1 d . . . O8 O 0.50162(15) 0.0227(3) -0.19481(12) 0.0728(8) Uani 1 1 d . . . N4 N 0.85888(14) -0.08178(19) 0.14441(11) 0.0276(5) Uani 1 1 d . . . N5 N 0.83183(14) 0.16485(19) 0.24931(10) 0.0284(5) Uani 1 1 d . . . H5A H 0.8312 0.2039 0.2901 0.034 Uiso 1 1 calc R . . N6 N 0.82335(14) 0.13824(19) 0.13052(10) 0.0278(5) Uani 1 1 d . . . N7 N 0.80166(14) -0.05440(19) 0.23548(11) 0.0288(5) Uani 1 1 d . . . H7A H 0.7651 -0.0640 0.2612 0.035 Uiso 1 1 calc R . . C9 C 0.86998(16) 0.0432(2) 0.25060(13) 0.0256(6) Uani 1 1 d . . . C10 C 0.88873(17) 0.0422(2) 0.17278(13) 0.0268(6) Uani 1 1 d . . . C11 C 0.95215(16) 0.0185(2) 0.32300(13) 0.0253(6) Uani 1 1 d . . . C12 C 1.10070(18) 0.2239(3) 0.18192(14) 0.0347(6) Uani 1 1 d . . . H12A H 1.1161 0.3076 0.1767 0.042 Uiso 1 1 calc R . . C13 C 1.00150(17) 0.1149(2) 0.36744(14) 0.0333(6) Uani 1 1 d . . . H13A H 0.9858 0.1979 0.3515 0.040 Uiso 1 1 calc R . . C14 C 0.79698(17) 0.2124(2) 0.17774(13) 0.0290(6) Uani 1 1 d . . . C15 C 0.98626(17) 0.0729(2) 0.17997(13) 0.0265(6) Uani 1 1 d . . . C16 C 0.97776(19) -0.1007(3) 0.34655(15) 0.0383(7) Uani 1 1 d . . . H16A H 0.9451 -0.1680 0.3164 0.046 Uiso 1 1 calc R . . C17 C 0.85706(18) -0.1302(2) 0.07105(13) 0.0329(6) Uani 1 1 d . . . H17A H 0.8695 -0.0615 0.0414 0.039 Uiso 1 1 calc R . . H17B H 0.7947 -0.1622 0.0421 0.039 Uiso 1 1 calc R . . C18 C 0.80047(17) -0.1290(2) 0.17731(13) 0.0282(6) Uani 1 1 d . . . C19 C 1.05358(17) -0.0178(2) 0.19583(14) 0.0318(6) Uani 1 1 d . . . H19A H 1.0383 -0.1016 0.2008 0.038 Uiso 1 1 calc R . . C20 C 1.07379(17) 0.0912(3) 0.43513(15) 0.0364(7) Uani 1 1 d . . . H20A H 1.1066 0.1586 0.4650 0.044 Uiso 1 1 calc R . . C21 C 1.09903(18) -0.0277(2) 0.45993(14) 0.0330(6) Uani 1 1 d . . . C22 C 1.16782(18) 0.1339(3) 0.19680(15) 0.0378(7) Uani 1 1 d . . . C23 C 1.01176(18) 0.1949(2) 0.17446(14) 0.0309(6) Uani 1 1 d . . . H23A H 0.9674 0.2589 0.1654 0.037 Uiso 1 1 calc R . . C24 C 1.0509(2) -0.1241(3) 0.41395(16) 0.0434(7) Uani 1 1 d . . . H24A H 1.0682 -0.2072 0.4288 0.052 Uiso 1 1 calc R . . C25 C 1.05911(19) -0.4150(3) 0.09566(15) 0.0375(7) Uani 1 1 d . . . C26 C 0.94276(19) -0.3243(3) 0.13398(15) 0.0371(7) Uani 1 1 d . . . H26A H 0.9081 -0.3247 0.1662 0.044 Uiso 1 1 calc R . . C27 C 0.81159(19) 0.1791(2) 0.05414(14) 0.0352(7) Uani 1 1 d . . . H27A H 0.8674 0.1567 0.0438 0.042 Uiso 1 1 calc R . . H27B H 0.8067 0.2705 0.0524 0.042 Uiso 1 1 calc R . . C28 C 0.92629(17) -0.2327(2) 0.07891(14) 0.0317(6) Uani 1 1 d . . . C29 C 0.97509(19) -0.2377(3) 0.03081(15) 0.0379(7) Uani 1 1 d . . . H29A H 0.9639 -0.1770 -0.0079 0.045 Uiso 1 1 calc R . . C30 C 0.72890(19) 0.1262(3) -0.00881(14) 0.0355(7) Uani 1 1 d . . . C31 C 1.14278(18) 0.0131(3) 0.20444(16) 0.0394(7) Uani 1 1 d . . . H31A H 1.1880 -0.0502 0.2159 0.047 Uiso 1 1 calc R . . C32 C 1.17407(19) -0.0537(3) 0.53521(15) 0.0436(7) Uani 1 1 d . . . H32A H 1.1989 0.0246 0.5605 0.065 Uiso 1 1 calc R . . H32B H 1.2231 -0.1010 0.5269 0.065 Uiso 1 1 calc R . . H32C H 1.1491 -0.1017 0.5673 0.065 Uiso 1 1 calc R . . C33 C 1.00861(19) -0.4151(3) 0.14301(14) 0.0364(7) Uani 1 1 d . . . H33A H 1.0191 -0.4768 0.1812 0.044 Uiso 1 1 calc R . . C34 C 1.0395(2) -0.3285(3) 0.03741(16) 0.0398(7) Uani 1 1 d . . . H34A H 1.0704 -0.3318 0.0023 0.048 Uiso 1 1 calc R . . C35 C 1.2646(2) 0.1672(3) 0.2049(2) 0.0622(10) Uani 1 1 d . . . H35A H 1.2683 0.2564 0.1969 0.093 Uiso 1 1 calc R . . H35B H 1.2817 0.1216 0.1671 0.093 Uiso 1 1 calc R . . H35C H 1.3067 0.1454 0.2561 0.093 Uiso 1 1 calc R . . C36 C 0.5757(2) 0.0527(3) -0.13073(16) 0.0491(8) Uani 1 1 d . . . C37 C 0.7239(2) 0.1410(3) -0.08313(15) 0.0460(8) Uani 1 1 d . . . H37A H 0.7743 0.1767 -0.0926 0.055 Uiso 1 1 calc R . . C38 C 1.1811(2) -0.5069(3) 0.0659(2) 0.0536(8) Uani 1 1 d . . . H38A H 1.2253 -0.5750 0.0827 0.080 Uiso 1 1 calc R . . H38B H 1.2142 -0.4284 0.0709 0.080 Uiso 1 1 calc R . . H38C H 1.1417 -0.5196 0.0126 0.080 Uiso 1 1 calc R . . C39 C 0.6478(2) 0.1050(3) -0.14304(16) 0.0513(8) Uani 1 1 d . . . H39A H 0.6455 0.1169 -0.1936 0.062 Uiso 1 1 calc R . . C40 C 0.6567(2) 0.0718(3) 0.00335(16) 0.0491(8) Uani 1 1 d . . . H40A H 0.6593 0.0600 0.0540 0.059 Uiso 1 1 calc R . . C41 C 0.4201(2) -0.0164(4) -0.1852(2) 0.0728(12) Uani 1 1 d . . . H41A H 0.3730 -0.0343 -0.2350 0.109 Uiso 1 1 calc R . . H41B H 0.3982 0.0492 -0.1602 0.109 Uiso 1 1 calc R . . H41C H 0.4325 -0.0913 -0.1537 0.109 Uiso 1 1 calc R . . C42 C 0.5790(2) 0.0331(4) -0.05708(18) 0.0580(9) Uani 1 1 d . . . H42A H 0.5294 -0.0059 -0.0480 0.070 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 0.0513(11) 0.0411(12) 0.0270(10) 0.0076(8) 0.0190(8) 0.0181(9) O2 0.0473(11) 0.0408(12) 0.0288(10) -0.0086(8) 0.0199(8) -0.0143(9) O3 0.0606(13) 0.0448(13) 0.0542(13) 0.0093(9) 0.0368(11) 0.0148(10) O8 0.0443(13) 0.135(2) 0.0345(14) -0.0197(13) 0.0085(11) 0.0108(13) N4 0.0375(12) 0.0296(13) 0.0212(11) -0.0030(9) 0.0170(9) -0.0021(9) N5 0.0414(12) 0.0315(13) 0.0143(11) 0.0012(8) 0.0126(9) 0.0061(9) N6 0.0369(12) 0.0328(13) 0.0170(11) 0.0024(9) 0.0138(9) 0.0041(9) N7 0.0337(11) 0.0355(13) 0.0241(12) -0.0030(9) 0.0186(9) -0.0035(9) C9 0.0328(13) 0.0268(15) 0.0209(14) -0.0001(10) 0.0142(11) 0.0016(10) C10 0.0342(14) 0.0276(15) 0.0224(14) 0.0018(10) 0.0149(11) 0.0017(11) C11 0.0318(14) 0.0299(16) 0.0203(13) 0.0009(10) 0.0169(11) 0.0000(11) C12 0.0464(16) 0.0298(16) 0.0317(15) -0.0020(11) 0.0185(12) -0.0079(12) C13 0.0385(15) 0.0265(15) 0.0340(16) 0.0023(11) 0.0122(12) 0.0001(11) C14 0.0337(14) 0.0318(16) 0.0242(14) 0.0007(11) 0.0140(11) 0.0015(12) C15 0.0356(14) 0.0299(15) 0.0175(13) -0.0019(10) 0.0136(11) -0.0012(11) C16 0.0535(17) 0.0281(17) 0.0265(15) -0.0017(11) 0.0064(13) -0.0006(13) C17 0.0446(16) 0.0376(17) 0.0198(14) -0.0021(11) 0.0157(12) -0.0022(12) C18 0.0333(14) 0.0323(16) 0.0224(14) -0.0012(11) 0.0143(11) -0.0008(12) C19 0.0378(15) 0.0274(15) 0.0323(15) 0.0014(11) 0.0154(12) -0.0006(11) C20 0.0362(15) 0.0351(17) 0.0338(16) -0.0044(12) 0.0076(12) -0.0071(12) C21 0.0387(15) 0.0400(18) 0.0233(14) 0.0029(12) 0.0149(12) 0.0006(12) C22 0.0372(15) 0.0408(18) 0.0379(16) -0.0037(12) 0.0166(12) -0.0045(13) C23 0.0401(15) 0.0294(16) 0.0284(14) 0.0019(11) 0.0185(11) 0.0021(12) C24 0.0587(18) 0.0298(17) 0.0338(17) 0.0062(12) 0.0071(14) 0.0059(13) C25 0.0464(16) 0.0325(17) 0.0386(16) -0.0004(12) 0.0212(13) -0.0003(13) C26 0.0485(16) 0.0414(18) 0.0302(15) -0.0015(12) 0.0250(12) -0.0034(13) C27 0.0509(17) 0.0348(17) 0.0259(15) 0.0060(11) 0.0210(13) 0.0036(12) C28 0.0419(15) 0.0346(16) 0.0207(13) -0.0029(11) 0.0138(11) -0.0051(11) C29 0.0543(17) 0.0388(17) 0.0289(15) 0.0040(11) 0.0250(13) -0.0005(13) C30 0.0459(16) 0.0391(17) 0.0250(15) 0.0055(11) 0.0169(12) 0.0118(12) C31 0.0360(15) 0.0366(18) 0.0456(17) -0.0017(12) 0.0147(13) 0.0030(12) C32 0.0429(16) 0.060(2) 0.0263(16) 0.0056(13) 0.0104(13) 0.0013(13) C33 0.0495(16) 0.0377(17) 0.0296(15) 0.0065(12) 0.0234(13) 0.0026(13) C34 0.0548(17) 0.0366(17) 0.0430(17) -0.0008(13) 0.0357(14) -0.0020(13) C35 0.0454(18) 0.051(2) 0.094(3) -0.0041(18) 0.0291(18) -0.0081(15) C36 0.0434(17) 0.073(2) 0.0295(17) -0.0119(14) 0.0114(14) 0.0145(15) C37 0.0575(19) 0.057(2) 0.0283(17) 0.0017(13) 0.0216(15) 0.0030(15) C38 0.058(2) 0.053(2) 0.063(2) 0.0086(15) 0.0381(17) 0.0099(15) C39 0.062(2) 0.068(2) 0.0274(17) 0.0006(14) 0.0206(15) 0.0099(16) C40 0.0489(18) 0.075(2) 0.0227(16) -0.0013(14) 0.0119(14) -0.0006(16) C41 0.042(2) 0.119(3) 0.054(2) -0.030(2) 0.0133(16) 0.0030(19) C42 0.0443(18) 0.096(3) 0.0372(19) -0.0058(16) 0.0187(15) -0.0024(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 O1 C14 1.227(3) . ? O2 C18 1.231(3) . ? O3 C25 1.369(3) . ? O3 C38 1.421(4) . ? O8 C36 1.375(4) . ? O8 C41 1.415(5) . ? N4 C18 1.374(3) . ? N4 C10 1.455(3) . ? N4 C17 1.470(3) . ? N5 C14 1.360(3) . ? N5 C9 1.440(3) . ? N6 C14 1.368(3) . ? N6 C27 1.453(3) . ? N6 C10 1.472(3) . ? N7 C18 1.356(3) . ? N7 C9 1.453(3) . ? C9 C11 1.521(3) . ? C9 C10 1.597(3) . ? C10 C15 1.517(4) . ? C11 C16 1.374(4) . ? C11 C13 1.383(4) . ? C12 C23 1.381(4) . ? C12 C22 1.382(4) . ? C13 C20 1.388(4) . ? C15 C19 1.389(4) . ? C15 C23 1.391(4) . ? C16 C24 1.391(4) . ? C17 C28 1.517(4) . ? C19 C31 1.384(4) . ? C20 C21 1.375(4) . ? C21 C24 1.389(4) . ? C21 C32 1.505(4) . ? C22 C31 1.386(4) . ? C22 C35 1.507(4) . ? C25 C33 1.389(4) . ? C25 C34 1.390(4) . ? C26 C33 1.387(4) . ? C26 C28 1.390(4) . ? C27 C30 1.514(4) . ? C28 C29 1.381(4) . ? C29 C34 1.378(4) . ? C30 C40 1.364(4) . ? C30 C37 1.384(4) . ? C36 C39 1.354(5) . ? C36 C42 1.388(4) . ? C37 C39 1.367(4) . ? C40 C42 1.395(4) . ? 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 C25 O3 C38 117.8(2) . . ? C36 O8 C41 117.9(3) . . ? C18 N4 C10 110.64(19) . . ? C18 N4 C17 120.2(2) . . ? C10 N4 C17 124.6(2) . . ? C14 N5 C9 112.10(19) . . ? C14 N6 C27 120.5(2) . . ? C14 N6 C10 111.99(19) . . ? C27 N6 C10 124.4(2) . . ? C18 N7 C9 112.6(2) . . ? N5 C9 N7 112.9(2) . . ? N5 C9 C11 112.61(19) . . ? N7 C9 C11 111.74(19) . . ? N5 C9 C10 101.72(17) . . ? N7 C9 C10 100.42(17) . . ? C11 C9 C10 116.59(19) . . ? N4 C10 N6 112.52(19) . . ? N4 C10 C15 114.36(19) . . ? N6 C10 C15 111.80(19) . . ? N4 C10 C9 101.73(18) . . ? N6 C10 C9 99.81(17) . . ? C15 C10 C9 115.40(19) . . ? C16 C11 C13 118.5(2) . . ? C16 C11 C9 120.4(2) . . ? C13 C11 C9 121.1(2) . . ? C23 C12 C22 121.5(2) . . ? C11 C13 C20 120.5(2) . . ? O1 C14 N5 126.9(2) . . ? O1 C14 N6 124.6(2) . . ? N5 C14 N6 108.5(2) . . ? C19 C15 C23 118.0(2) . . ? C19 C15 C10 121.5(2) . . ? C23 C15 C10 120.4(2) . . ? C11 C16 C24 120.8(3) . . ? N4 C17 C28 113.4(2) . . ? O2 C18 N7 126.4(2) . . ? O2 C18 N4 124.5(2) . . ? N7 C18 N4 109.1(2) . . ? C31 C19 C15 120.5(2) . . ? C21 C20 C13 121.5(2) . . ? C20 C21 C24 117.7(2) . . ? C20 C21 C32 121.6(2) . . ? C24 C21 C32 120.7(2) . . ? C12 C22 C31 117.5(2) . . ? C12 C22 C35 120.8(3) . . ? C31 C22 C35 121.7(3) . . ? C12 C23 C15 120.8(2) . . ? C21 C24 C16 120.9(3) . . ? O3 C25 C33 115.2(2) . . ? O3 C25 C34 125.2(2) . . ? C33 C25 C34 119.7(2) . . ? C33 C26 C28 121.6(2) . . ? N6 C27 C30 115.4(2) . . ? C29 C28 C26 117.8(2) . . ? C29 C28 C17 120.6(2) . . ? C26 C28 C17 121.7(2) . . ? C34 C29 C28 121.8(2) . . ? C40 C30 C37 118.2(3) . . ? C40 C30 C27 123.6(2) . . ? C37 C30 C27 118.0(3) . . ? C19 C31 C22 121.7(3) . . ? C26 C33 C25 119.3(2) . . ? C29 C34 C25 119.6(2) . . ? C39 C36 O8 115.8(3) . . ? C39 C36 C42 120.3(3) . . ? O8 C36 C42 123.9(3) . . ? C39 C37 C30 121.1(3) . . ? C36 C39 C37 120.4(3) . . ? C30 C40 C42 121.4(3) . . ? C36 C42 C40 118.5(3) . . ? _diffrn_measured_fraction_theta_max 0.904 _diffrn_reflns_theta_full 56.41 _diffrn_measured_fraction_theta_full 0.904 _refine_diff_density_max 0.383 _refine_diff_density_min -0.304 _refine_diff_density_rms 0.056 data_glycods _database_code_CSD 184671 _audit_creation_method SHELXL-97 _computing_data_collection 'SMART (Siemens, 1995)' _computing_cell_refinement ; SMART (Siemens, 1995), SAINT (Siemens, 1995) ; _computing_data_reduction ; SAINT (Siemens, 1995), XPREP (Siemens, 1995) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' 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(2)1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' #------------------------------------------------------------------------------ _cell_length_a 11.631(5) _cell_length_b 10.602(4) _cell_length_c 11.995(5) _cell_angle_alpha 90.00 _cell_angle_beta 116.54(3) _cell_angle_gamma 90.00 _cell_volume 1323.3(9) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 3252 _cell_measurement_theta_min 1.9 _cell_measurement_theta_max 23.25 #------------------------------------------------------------------------------ _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.321 _exptl_crystal_F_000 556 _chemical_formula_sum 'C26 H30 N4 O8' _chemical_formula_weight 526.54 _chemical_compound_source 'synthetic' _exptl_absorpt_coefficient_mu 0.099 _exptl_absorpt_correction_type 'psi-scan' _exptl_absorpt_correction_T_min 0.759 _exptl_absorpt_correction_T_max 0.991 _exptl_special_details ; ? ; #------------------------------------------------------------------------------ _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'X-ray tube' _diffrn_radiation_monochromator graphite _diffrn_radiation_detector 'CCD area detector' _diffrn_measurement_device_type '3 circle diffractometer' _diffrn_measurement_method ; omega scans with profile analysis ; _diffrn_reflns_number 4642 _diffrn_reflns_av_R_equivalents 0.0203 _diffrn_reflns_av_sigmaI/netI 0.0417 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.90 _diffrn_reflns_theta_max 23.25 _reflns_number_total 3544 _reflns_number_gt 3306 _reflns_threshold_expression >2sigma(I) _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. Flack parameter refined to unambiguous value (ca. 0.5) therefore a twin and basf command was added in shelxl. This led to the modeling of the structure as a 50% (within the esd of the basf paramter) racemic twin. ; _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^)+(0.0523P)^2^+0.2055P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.5(11) _refine_ls_number_reflns 3544 _refine_ls_number_parameters 344 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0422 _refine_ls_R_factor_gt 0.0391 _refine_ls_wR_factor_ref 0.1014 _refine_ls_wR_factor_gt 0.0986 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.056 _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 -0.54931(18) -0.51582(19) -0.36167(17) 0.0521(5) Uani 1 1 d . . . O5 O -0.71125(19) -0.0237(2) -0.5605(2) 0.0586(5) Uani 1 1 d . . . O26 O -1.1762(2) -0.4642(3) -1.0930(2) 0.0829(7) Uani 1 1 d . . . O31 O -0.5391(3) -0.5767(4) -0.9936(3) 0.1151(11) Uani 1 1 d . . . N1 N -0.54246(18) -0.3709(2) -0.50254(19) 0.0453(5) Uani 1 1 d . . . H1A H -0.4624 -0.3511 -0.4644 0.054 Uiso 1 1 calc R . . N3 N -0.72955(18) -0.4508(2) -0.53291(19) 0.0405(5) Uani 1 1 d . . . N6 N -0.78138(19) -0.2284(2) -0.57137(19) 0.0427(5) Uani 1 1 d . . . N10 N -0.6324(2) -0.1881(2) -0.6320(2) 0.0483(6) Uani 1 1 d . . . H10A H -0.5903 -0.1457 -0.6627 0.058 Uiso 1 1 calc R . . O2 O -0.79050(18) -0.71265(18) -0.38817(18) 0.0531(5) Uani 1 1 d . . . C3 C -0.6009(2) -0.4511(2) -0.4563(2) 0.0409(6) Uani 1 1 d . . . C4 C -0.9492(6) -0.4049(7) -0.2355(5) 0.145(2) Uani 1 1 d . . . H4A H -0.9332 -0.4242 -0.1517 0.218 Uiso 1 1 calc R . . H4B H -0.9020 -0.4624 -0.2615 0.218 Uiso 1 1 calc R . . H4C H -1.0394 -0.4128 -0.2899 0.218 Uiso 1 1 calc R . . C5 C -0.8131(3) -0.5236(3) -0.4969(3) 0.0462(6) Uani 1 1 d . . . H5A H -0.9012 -0.5165 -0.5606 0.055 Uiso 1 1 calc R . . H5B H -0.8085 -0.4909 -0.4195 0.055 Uiso 1 1 calc R . . O7 O -0.7321(2) -0.7154(2) -0.5425(2) 0.0700(6) Uani 1 1 d . . . C8 C -0.9571(2) -0.2828(3) -0.8196(3) 0.0485(7) Uani 1 1 d . . . H8A H -0.9420 -0.2003 -0.7902 0.058 Uiso 1 1 calc R . . C9 C -0.7650(2) -0.3491(2) -0.6218(2) 0.0398(6) Uani 1 1 d . . . C10 C -0.7724(3) -0.6604(3) -0.4803(3) 0.0482(7) Uani 1 1 d . . . C12 C -0.8992(3) -0.4998(3) -0.7952(3) 0.0489(7) Uani 1 1 d . . . H12A H -0.8462 -0.5654 -0.7491 0.059 Uiso 1 1 calc R . . C13 C -0.6312(2) -0.3219(2) -0.6249(2) 0.0402(6) Uani 1 1 d . . . C14 C -1.0587(3) -0.3070(3) -0.9350(3) 0.0533(7) Uani 1 1 d . . . H14A H -1.1122 -0.2419 -0.9815 0.064 Uiso 1 1 calc R . . C15 C -0.6121(2) -0.3862(3) -0.7281(2) 0.0445(6) Uani 1 1 d . . . C16 C -0.8776(2) -0.3776(3) -0.7470(2) 0.0397(6) Uani 1 1 d . . . C17 C -0.7078(2) -0.1344(3) -0.5845(2) 0.0447(6) Uani 1 1 d . . . C18 C -0.8756(2) -0.2049(3) -0.5273(2) 0.0476(6) Uani 1 1 d . . . H18A H -0.9525 -0.2528 -0.5777 0.057 Uiso 1 1 calc R . . H18B H -0.8982 -0.1161 -0.5383 0.057 Uiso 1 1 calc R . . C19 C -1.0796(3) -0.4287(3) -0.9804(3) 0.0552(7) Uani 1 1 d . . . C20 C -0.9989(3) -0.5235(3) -0.9113(3) 0.0583(8) Uani 1 1 d . . . H20A H -1.0116 -0.6051 -0.9432 0.070 Uiso 1 1 calc R . . O21 O -0.9310(2) -0.2430(3) -0.3676(2) 0.0838(8) Uani 1 1 d . . . C22 C -0.5689(3) -0.5111(3) -0.7145(3) 0.0532(7) Uani 1 1 d . . . H22A H -0.5550 -0.5552 -0.6426 0.064 Uiso 1 1 calc R . . O23 O -0.7229(2) -0.2617(2) -0.3194(2) 0.0769(7) Uani 1 1 d . . . C24 C -0.8308(3) -0.2391(3) -0.3926(3) 0.0518(7) Uani 1 1 d . . . C27 C -0.5466(3) -0.5699(4) -0.8045(3) 0.0639(8) Uani 1 1 d . . . H27A H -0.5169 -0.6526 -0.7921 0.077 Uiso 1 1 calc R . . C29 C -0.5669(3) -0.5100(4) -0.9109(3) 0.0737(10) Uani 1 1 d . . . C30 C -0.6339(3) -0.3248(3) -0.8366(3) 0.0614(8) Uani 1 1 d . . . H30A H -0.6639 -0.2421 -0.8493 0.074 Uiso 1 1 calc R . . C32 C -1.2629(4) -0.3693(5) -1.1689(4) 0.1064(15) Uani 1 1 d . . . H32A H -1.3253 -0.4067 -1.2448 0.160 Uiso 1 1 calc R . . H32B H -1.2158 -0.3057 -1.1882 0.160 Uiso 1 1 calc R . . H32C H -1.3058 -0.3318 -1.1249 0.160 Uiso 1 1 calc R . . C33 C -0.7704(4) -0.8863(4) -0.2540(4) 0.0915(12) Uani 1 1 d . . . H33A H -0.7451 -0.9731 -0.2364 0.137 Uiso 1 1 calc R . . H33B H -0.8595 -0.8780 -0.2732 0.137 Uiso 1 1 calc R . . H33C H -0.7194 -0.8356 -0.1825 0.137 Uiso 1 1 calc R . . C34 C -0.7511(4) -0.8443(3) -0.3600(4) 0.0725(9) Uani 1 1 d . . . H34A H -0.8011 -0.8964 -0.4320 0.087 Uiso 1 1 calc R . . H34B H -0.6612 -0.8527 -0.3410 0.087 Uiso 1 1 calc R . . C35 C -0.6110(3) -0.3865(4) -0.9291(3) 0.0764(10) Uani 1 1 d . . . H35A H -0.6254 -0.3444 -1.0022 0.092 Uiso 1 1 calc R . . C36 C -0.9086(5) -0.2781(6) -0.2409(4) 0.1040(16) Uani 1 1 d . . . H36A H -0.8177 -0.2701 -0.1849 0.125 Uiso 1 1 calc R . . H36B H -0.9550 -0.2204 -0.2129 0.125 Uiso 1 1 calc R . . C37 C -0.5490(7) -0.5197(8) -1.0997(5) 0.151(3) Uani 1 1 d . . . H37A H -0.5280 -0.5794 -1.1480 0.226 Uiso 1 1 calc R . . H37B H -0.4906 -0.4497 -1.0780 0.226 Uiso 1 1 calc R . . H37C H -0.6353 -0.4901 -1.1477 0.226 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 0.0523(11) 0.0640(13) 0.0423(10) 0.0020(10) 0.0231(9) 0.0145(9) O5 0.0627(12) 0.0415(12) 0.0740(14) -0.0130(10) 0.0327(11) -0.0069(9) O26 0.0784(15) 0.0850(18) 0.0527(13) -0.0099(12) 0.0001(11) -0.0097(13) O31 0.149(3) 0.142(3) 0.0741(17) -0.0093(18) 0.0674(19) 0.033(2) N1 0.0314(10) 0.0626(15) 0.0410(11) -0.0045(11) 0.0154(9) -0.0030(10) N3 0.0369(11) 0.0412(13) 0.0420(12) 0.0019(10) 0.0163(9) -0.0001(9) N6 0.0390(10) 0.0415(13) 0.0520(12) -0.0068(10) 0.0243(9) -0.0012(9) N10 0.0490(13) 0.0413(13) 0.0637(15) -0.0048(11) 0.0333(12) -0.0100(10) O2 0.0646(11) 0.0477(12) 0.0598(12) 0.0064(9) 0.0393(10) 0.0051(9) C3 0.0438(14) 0.0422(15) 0.0392(14) -0.0067(12) 0.0207(12) 0.0070(12) C4 0.169(5) 0.181(7) 0.098(4) 0.026(4) 0.072(4) -0.046(5) C5 0.0489(15) 0.0466(16) 0.0511(15) -0.0022(13) 0.0295(13) -0.0021(12) O7 0.1102(17) 0.0484(14) 0.0809(15) -0.0038(11) 0.0692(15) 0.0034(12) C8 0.0460(14) 0.0427(16) 0.0531(16) -0.0008(13) 0.0187(13) -0.0030(12) C9 0.0375(13) 0.0387(15) 0.0475(14) -0.0008(12) 0.0228(11) -0.0010(10) C10 0.0542(16) 0.0467(17) 0.0525(16) -0.0040(13) 0.0319(14) -0.0055(12) C12 0.0480(15) 0.0451(17) 0.0509(15) -0.0030(13) 0.0197(13) 0.0006(12) C13 0.0351(13) 0.0445(16) 0.0425(14) -0.0040(11) 0.0185(11) -0.0041(10) C14 0.0465(15) 0.0529(19) 0.0525(17) 0.0085(14) 0.0149(13) 0.0006(13) C15 0.0329(12) 0.0577(18) 0.0436(15) -0.0075(13) 0.0178(11) -0.0051(12) C16 0.0359(12) 0.0432(15) 0.0435(13) -0.0009(12) 0.0209(11) -0.0024(11) C17 0.0425(15) 0.0397(17) 0.0472(15) -0.0050(13) 0.0159(12) -0.0028(12) C18 0.0400(14) 0.0515(17) 0.0519(16) -0.0027(13) 0.0211(12) 0.0057(12) C19 0.0477(15) 0.068(2) 0.0411(15) 0.0003(14) 0.0117(13) -0.0070(14) C20 0.0622(18) 0.0529(18) 0.0514(16) -0.0129(15) 0.0179(15) -0.0067(15) O21 0.0727(14) 0.128(2) 0.0645(14) 0.0174(14) 0.0429(12) 0.0244(14) C22 0.0530(16) 0.0585(19) 0.0525(16) -0.0048(14) 0.0275(13) 0.0013(14) O23 0.0598(14) 0.0989(19) 0.0585(13) -0.0036(12) 0.0142(11) 0.0082(12) C24 0.0547(17) 0.0480(17) 0.0545(17) -0.0117(14) 0.0260(15) 0.0048(13) C27 0.0605(18) 0.072(2) 0.062(2) -0.0143(17) 0.0299(15) 0.0052(16) C29 0.073(2) 0.099(3) 0.054(2) -0.014(2) 0.0336(17) 0.013(2) C30 0.0589(18) 0.074(2) 0.0555(18) 0.0068(16) 0.0297(14) 0.0079(15) C32 0.084(2) 0.108(3) 0.066(2) -0.002(2) -0.0206(19) 0.004(2) C33 0.094(3) 0.083(3) 0.114(3) 0.039(2) 0.062(2) 0.026(2) C34 0.097(2) 0.051(2) 0.090(2) 0.0114(18) 0.059(2) 0.0146(17) C35 0.077(2) 0.112(3) 0.0427(17) 0.0142(19) 0.0289(15) 0.006(2) C36 0.117(3) 0.149(5) 0.066(2) 0.012(3) 0.059(2) 0.036(3) C37 0.199(6) 0.201(7) 0.084(3) 0.014(4) 0.091(4) 0.059(5) _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 C3 1.229(3) . ? O5 C17 1.214(3) . ? O26 C19 1.368(4) . ? O26 C32 1.427(5) . ? O31 C37 1.367(6) . ? O31 C29 1.369(4) . ? N1 C3 1.353(3) . ? N1 C13 1.461(3) . ? N3 C3 1.362(3) . ? N3 C9 1.440(3) . ? N3 C5 1.450(3) . ? N6 C17 1.368(4) . ? N6 C18 1.435(3) . ? N6 C9 1.464(3) . ? N10 C17 1.366(3) . ? N10 C13 1.421(4) . ? O2 C10 1.334(3) . ? O2 C34 1.460(4) . ? C4 C36 1.435(8) . ? C5 C10 1.511(4) . ? O7 C10 1.195(3) . ? C8 C16 1.380(4) . ? C8 C14 1.384(4) . ? C9 C16 1.519(4) . ? C9 C13 1.599(3) . ? C12 C20 1.380(4) . ? C12 C16 1.395(4) . ? C13 C15 1.514(4) . ? C14 C19 1.380(4) . ? C15 C30 1.375(4) . ? C15 C22 1.399(4) . ? C18 C24 1.504(4) . ? C19 C20 1.372(5) . ? O21 C24 1.327(4) . ? O21 C36 1.470(5) . ? C22 C27 1.367(4) . ? O23 C24 1.191(3) . ? C27 C29 1.348(5) . ? C29 C35 1.387(6) . ? C30 C35 1.412(5) . ? C33 C34 1.457(5) . ? 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 C19 O26 C32 118.1(3) . . ? C37 O31 C29 119.9(4) . . ? C3 N1 C13 112.12(19) . . ? C3 N3 C9 111.5(2) . . ? C3 N3 C5 118.5(2) . . ? C9 N3 C5 127.7(2) . . ? C17 N6 C18 122.4(2) . . ? C17 N6 C9 112.7(2) . . ? C18 N6 C9 124.5(2) . . ? C17 N10 C13 112.4(2) . . ? C10 O2 C34 116.0(2) . . ? O1 C3 N1 127.0(2) . . ? O1 C3 N3 124.1(2) . . ? N1 C3 N3 108.9(2) . . ? N3 C5 C10 109.8(2) . . ? C16 C8 C14 121.9(3) . . ? N3 C9 N6 113.3(2) . . ? N3 C9 C16 114.7(2) . . ? N6 C9 C16 111.6(2) . . ? N3 C9 C13 101.12(18) . . ? N6 C9 C13 99.19(18) . . ? C16 C9 C13 115.52(19) . . ? O7 C10 O2 124.5(3) . . ? O7 C10 C5 124.9(3) . . ? O2 C10 C5 110.6(2) . . ? C20 C12 C16 120.1(3) . . ? N10 C13 N1 113.5(2) . . ? N10 C13 C15 113.7(2) . . ? N1 C13 C15 111.4(2) . . ? N10 C13 C9 101.42(19) . . ? N1 C13 C9 99.80(18) . . ? C15 C13 C9 116.0(2) . . ? C19 C14 C8 119.3(3) . . ? C30 C15 C22 117.6(3) . . ? C30 C15 C13 121.9(3) . . ? C22 C15 C13 120.5(2) . . ? C8 C16 C12 118.0(2) . . ? C8 C16 C9 121.2(2) . . ? C12 C16 C9 120.7(2) . . ? O5 C17 N10 126.7(3) . . ? O5 C17 N6 126.1(3) . . ? N10 C17 N6 107.2(2) . . ? N6 C18 C24 113.5(2) . . ? O26 C19 C20 115.7(3) . . ? O26 C19 C14 124.7(3) . . ? C20 C19 C14 119.6(3) . . ? C19 C20 C12 121.0(3) . . ? C24 O21 C36 118.2(3) . . ? C27 C22 C15 121.6(3) . . ? O23 C24 O21 124.8(3) . . ? O23 C24 C18 125.9(3) . . ? O21 C24 C18 109.4(2) . . ? C29 C27 C22 121.2(3) . . ? C27 C29 O31 116.4(4) . . ? C27 C29 C35 119.3(3) . . ? O31 C29 C35 124.3(4) . . ? C15 C30 C35 120.3(3) . . ? C33 C34 O2 109.8(3) . . ? C29 C35 C30 120.0(3) . . ? C4 C36 O21 111.9(4) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 23.25 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.209 _refine_diff_density_min -0.216 _refine_diff_density_rms 0.048 data_tbuglys _database_code_CSD 184672 _audit_creation_method SHELXL-97 _computing_data_collection 'SMART (Siemens, 1995)' _computing_cell_refinement ; SMART (Siemens, 1995), SAINT (Siemens, 1995) ; _computing_data_reduction ; SAINT (Siemens, 1995), XPREP (Siemens, 1995) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #------------------------------------------------------------------------------ _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' #------------------------------------------------------------------------------ _cell_length_a 34.4274(10) _cell_length_b 10.8215(3) _cell_length_c 21.6985(6) _cell_angle_alpha 90.00 _cell_angle_beta 91.115(2) _cell_angle_gamma 90.00 _cell_volume 8082.4(4) _cell_formula_units_Z 8 _cell_measurement_temperature 118(2) _cell_measurement_reflns_used 6137 _cell_measurement_theta_min 2.566 _cell_measurement_theta_max 56.114 #------------------------------------------------------------------------------ _exptl_crystal_description 'thin plate' _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.183 _exptl_crystal_F_000 3088 _chemical_formula_sum 'C43 H53 N5 O5' _chemical_formula_weight 719.90 _chemical_compound_source 'synthetic' _exptl_absorpt_coefficient_mu 0.622 _exptl_absorpt_correction_type 'psi-scan' _exptl_absorpt_correction_T_min 0.399239 _exptl_absorpt_correction_T_max 0.928540 _exptl_special_details ; ? ; #------------------------------------------------------------------------------ _diffrn_ambient_temperature 118(2) _diffrn_radiation_wavelength 1.54180 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'X-ray tube' _diffrn_radiation_monochromator 'mirror optics' _diffrn_radiation_detector 'CCD area detector' _diffrn_measurement_device_type '3 circle diffractometer' _diffrn_measurement_method ; omega scans with profile analysis ; _diffrn_reflns_number 12628 _diffrn_reflns_av_R_equivalents 0.0297 _diffrn_reflns_av_sigmaI/netI 0.0314 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_h_max 36 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.57 _diffrn_reflns_theta_max 56.38 _reflns_number_total 4776 _reflns_number_gt 3697 _reflns_threshold_expression >2sigma(I) _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^)+(0.0894P)^2^+2.4937P] 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 4776 _refine_ls_number_parameters 478 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0630 _refine_ls_R_factor_gt 0.0484 _refine_ls_wR_factor_ref 0.1410 _refine_ls_wR_factor_gt 0.1336 _refine_ls_goodness_of_fit_ref 1.073 _refine_ls_restrained_S_all 1.073 _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 0.22097(5) 0.86824(15) 0.16949(7) 0.0315(5) Uani 1 1 d . . . O2 O 0.20295(5) 0.34377(15) 0.21894(7) 0.0319(5) Uani 1 1 d . . . O3 O 0.08277(6) 1.27983(16) 0.22540(8) 0.0437(5) Uani 1 1 d . . . O4 O 0.16630(6) 0.69714(16) -0.07974(7) 0.0428(5) Uani 1 1 d . . . O5 O -0.01726(12) 1.1844(4) 0.11954(19) 0.1575(16) Uani 1 1 d . . . N1 N 0.22844(6) 0.71379(17) 0.24260(8) 0.0258(5) Uani 1 1 d . . . H1A H 0.2540 0.7112 0.2447 0.031 Uiso 1 1 calc R . . N2 N 0.16917(6) 0.75406(17) 0.20474(8) 0.0244(5) Uani 1 1 d . . . N3 N 0.21245(6) 0.51189(17) 0.28344(8) 0.0260(5) Uani 1 1 d . . . H3A H 0.2272 0.4767 0.3120 0.031 Uiso 1 1 calc R . . N4 N 0.16971(6) 0.52774(18) 0.20562(8) 0.0255(5) Uani 1 1 d . . . N5 N -0.07327(8) 1.0935(2) 0.08825(12) 0.0544(7) Uani 1 1 d . . . C1 C 0.20764(8) 0.7851(2) 0.20247(11) 0.0270(6) Uani 1 1 d . . . C2 C 0.20274(8) 0.6417(2) 0.28196(10) 0.0267(6) Uani 1 1 d . . . C3 C 0.16419(7) 0.6423(2) 0.24118(10) 0.0246(6) Uani 1 1 d . . . C4 C 0.19591(7) 0.4516(2) 0.23492(11) 0.0266(6) Uani 1 1 d . . . C5 C 0.19871(7) 0.6982(2) 0.34556(10) 0.0256(6) Uani 1 1 d . . . C6 C 0.20573(7) 0.8224(2) 0.35604(10) 0.0277(6) Uani 1 1 d . . . H6A H 0.2147 0.8729 0.3234 0.033 Uiso 1 1 calc R . . C7 C 0.19977(7) 0.8744(2) 0.41380(10) 0.0289(6) Uani 1 1 d . . . H7A H 0.2046 0.9600 0.4198 0.035 Uiso 1 1 calc R . . C8 C 0.18684(7) 0.8037(2) 0.46292(10) 0.0281(6) Uani 1 1 d . . . C9 C 0.17967(8) 0.6792(2) 0.45121(11) 0.0311(7) Uani 1 1 d . . . H9A H 0.1706 0.6286 0.4837 0.037 Uiso 1 1 calc R . . C10 C 0.18521(7) 0.6267(2) 0.39420(10) 0.0289(7) Uani 1 1 d . . . H10A H 0.1798 0.5414 0.3880 0.035 Uiso 1 1 calc R . . C11 C 0.18086(8) 0.8555(2) 0.52775(10) 0.0295(7) Uani 1 1 d . . . C12 C 0.20789(8) 0.7883(2) 0.57335(11) 0.0382(7) Uani 1 1 d . . . H12A H 0.2027 0.6994 0.5716 0.057 Uiso 1 1 calc R . . H12B H 0.2034 0.8188 0.6151 0.057 Uiso 1 1 calc R . . H12C H 0.2350 0.8037 0.5625 0.057 Uiso 1 1 calc R . . C13 C 0.13867(8) 0.8340(3) 0.54672(12) 0.0407(7) Uani 1 1 d . . . H13A H 0.1211 0.8770 0.5179 0.061 Uiso 1 1 calc R . . H13B H 0.1350 0.8660 0.5885 0.061 Uiso 1 1 calc R . . H13C H 0.1330 0.7453 0.5459 0.061 Uiso 1 1 calc R . . C14 C 0.19008(9) 0.9941(2) 0.53168(12) 0.0418(8) Uani 1 1 d . . . H14A H 0.1730 1.0395 0.5030 0.063 Uiso 1 1 calc R . . H14B H 0.2172 1.0079 0.5208 0.063 Uiso 1 1 calc R . . H14C H 0.1859 1.0233 0.5738 0.063 Uiso 1 1 calc R . . C15 C 0.12683(7) 0.6406(2) 0.27713(10) 0.0268(6) Uani 1 1 d . . . C16 C 0.10990(8) 0.7498(2) 0.29775(11) 0.0319(7) Uani 1 1 d . . . H16A H 0.1208 0.8272 0.2867 0.038 Uiso 1 1 calc R . . C17 C 0.07752(8) 0.7462(3) 0.33404(12) 0.0393(8) Uani 1 1 d . . . H17A H 0.0662 0.8220 0.3467 0.047 Uiso 1 1 calc R . . C18 C 0.06074(8) 0.6358(3) 0.35285(12) 0.0397(7) Uani 1 1 d . . . C19 C 0.07788(8) 0.5280(2) 0.33251(11) 0.0371(7) Uani 1 1 d . . . H19A H 0.0672 0.4507 0.3442 0.045 Uiso 1 1 calc R . . C20 C 0.11032(8) 0.5299(2) 0.29536(11) 0.0320(7) Uani 1 1 d . . . H20A H 0.1214 0.4541 0.2822 0.038 Uiso 1 1 calc R . . C21 C 0.02531(10) 0.6368(3) 0.39457(14) 0.0554(9) Uani 1 1 d . . . C22 C -0.00852(12) 0.6940(5) 0.3598(2) 0.126(2) Uani 1 1 d . . . H22A H -0.0139 0.6466 0.3222 0.190 Uiso 1 1 calc R . . H22B H -0.0022 0.7795 0.3490 0.190 Uiso 1 1 calc R . . H22C H -0.0315 0.6932 0.3858 0.190 Uiso 1 1 calc R . . C23 C 0.01306(10) 0.5063(3) 0.41386(15) 0.0638(10) Uani 1 1 d . . . H23A H 0.0343 0.4672 0.4373 0.096 Uiso 1 1 calc R . . H23B H 0.0070 0.4571 0.3770 0.096 Uiso 1 1 calc R . . H23C H -0.0100 0.5114 0.4396 0.096 Uiso 1 1 calc R . . C24 C 0.03610(13) 0.7054(4) 0.45436(17) 0.0991(16) Uani 1 1 d . . . H24A H 0.0583 0.6643 0.4746 0.149 Uiso 1 1 calc R . . H24B H 0.0139 0.7046 0.4819 0.149 Uiso 1 1 calc R . . H24C H 0.0430 0.7910 0.4448 0.149 Uiso 1 1 calc R . . C25 C 0.14065(8) 0.8050(2) 0.16141(11) 0.0296(7) Uani 1 1 d . . . H25A H 0.1186 0.7465 0.1575 0.036 Uiso 1 1 calc R . . H25B H 0.1527 0.8116 0.1205 0.036 Uiso 1 1 calc R . . C26 C 0.12487(8) 0.9317(2) 0.17927(10) 0.0275(6) Uani 1 1 d . . . C27 C 0.08755(8) 0.9638(2) 0.16199(12) 0.0339(7) Uani 1 1 d . . . H27A H 0.0719 0.9056 0.1400 0.041 Uiso 1 1 calc R . . C28 C 0.07190(8) 1.0797(2) 0.17584(12) 0.0370(7) Uani 1 1 d . . . H28A H 0.0461 1.1003 0.1633 0.044 Uiso 1 1 calc R . . C29 C 0.09480(8) 1.1637(2) 0.20821(12) 0.0336(7) Uani 1 1 d . . . C30 C 0.13235(9) 1.1327(2) 0.22582(11) 0.0348(7) Uani 1 1 d . . . H30A H 0.1480 1.1906 0.2480 0.042 Uiso 1 1 calc R . . C31 C 0.14728(8) 1.0184(2) 0.21147(11) 0.0306(7) Uani 1 1 d . . . H31A H 0.1732 0.9984 0.2237 0.037 Uiso 1 1 calc R . . C32 C 0.04763(10) 1.3229(3) 0.19944(16) 0.0639(10) Uani 1 1 d . . . H32A H 0.0422 1.4058 0.2153 0.096 Uiso 1 1 calc R . . H32B H 0.0265 1.2668 0.2104 0.096 Uiso 1 1 calc R . . H32C H 0.0497 1.3263 0.1545 0.096 Uiso 1 1 calc R . . C33 C 0.14381(7) 0.4841(2) 0.15654(10) 0.0284(6) Uani 1 1 d . . . H33A H 0.1167 0.5015 0.1681 0.034 Uiso 1 1 calc R . . H33B H 0.1466 0.3934 0.1529 0.034 Uiso 1 1 calc R . . C34 C 0.15121(8) 0.5423(2) 0.09418(10) 0.0265(6) Uani 1 1 d . . . C35 C 0.18788(8) 0.5813(2) 0.07732(11) 0.0311(7) Uani 1 1 d . . . H35A H 0.2092 0.5717 0.1055 0.037 Uiso 1 1 calc R . . C36 C 0.19408(8) 0.6345(2) 0.01965(11) 0.0323(7) Uani 1 1 d . . . H36A H 0.2193 0.6617 0.0090 0.039 Uiso 1 1 calc R . . C37 C 0.16357(9) 0.6472(2) -0.02163(11) 0.0335(7) Uani 1 1 d . . . C38 C 0.12675(8) 0.6087(2) -0.00563(11) 0.0363(7) Uani 1 1 d . . . H38A H 0.1056 0.6177 -0.0340 0.044 Uiso 1 1 calc R . . C39 C 0.12091(8) 0.5569(2) 0.05198(11) 0.0333(7) Uani 1 1 d . . . H39A H 0.0956 0.5310 0.0627 0.040 Uiso 1 1 calc R . . C40 C 0.20392(9) 0.7328(3) -0.09924(12) 0.0495(9) Uani 1 1 d . . . H40A H 0.2021 0.7653 -0.1414 0.074 Uiso 1 1 calc R . . H40B H 0.2212 0.6609 -0.0982 0.074 Uiso 1 1 calc R . . H40C H 0.2143 0.7969 -0.0716 0.074 Uiso 1 1 calc R . . C41 C -0.04934(15) 1.1390(5) 0.1301(2) 0.1024(15) Uani 1 1 d . . . H41A H -0.0573 1.1368 0.1717 0.123 Uiso 1 1 calc R . . C42 C -0.11045(9) 1.0460(3) 0.10458(14) 0.0571(9) Uani 1 1 d . . . H42A H -0.1129 1.0483 0.1495 0.086 Uiso 1 1 calc R . . H42B H -0.1129 0.9605 0.0901 0.086 Uiso 1 1 calc R . . H42C H -0.1309 1.0966 0.0853 0.086 Uiso 1 1 calc R . . C43 C -0.06374(12) 1.0958(3) 0.02324(16) 0.0795(12) Uani 1 1 d . . . H43A H -0.0375 1.1295 0.0185 0.119 Uiso 1 1 calc R . . H43B H -0.0825 1.1479 0.0008 0.119 Uiso 1 1 calc R . . H43C H -0.0647 1.0116 0.0066 0.119 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 0.0455(11) 0.0325(10) 0.0168(9) 0.0056(8) 0.0062(8) -0.0052(9) O2 0.0476(12) 0.0252(10) 0.0228(10) -0.0062(8) 0.0007(8) 0.0028(8) O3 0.0588(14) 0.0277(10) 0.0446(12) -0.0067(9) -0.0016(10) 0.0067(10) O4 0.0648(14) 0.0437(11) 0.0201(10) 0.0081(9) 0.0081(9) 0.0026(10) O5 0.112(3) 0.172(4) 0.186(4) -0.017(3) -0.042(3) -0.067(3) N1 0.0343(13) 0.0292(12) 0.0140(11) 0.0048(10) 0.0057(10) 0.0039(10) N2 0.0366(14) 0.0234(11) 0.0132(11) 0.0032(9) 0.0006(9) -0.0004(10) N3 0.0479(14) 0.0227(11) 0.0073(11) -0.0001(9) -0.0026(9) 0.0011(10) N4 0.0405(13) 0.0235(11) 0.0126(11) -0.0021(10) -0.0003(10) 0.0017(11) N5 0.0608(18) 0.0583(17) 0.0439(17) -0.0051(14) -0.0057(14) -0.0117(15) C1 0.0448(18) 0.0249(14) 0.0114(14) -0.0045(12) 0.0054(12) 0.0011(14) C2 0.0435(17) 0.0244(14) 0.0124(13) 0.0004(11) 0.0036(12) 0.0015(13) C3 0.0427(17) 0.0208(13) 0.0104(13) 0.0002(11) 0.0036(11) -0.0008(12) C4 0.0401(16) 0.0274(15) 0.0127(14) 0.0023(13) 0.0080(12) -0.0018(14) C5 0.0376(16) 0.0245(14) 0.0148(13) -0.0001(11) 0.0007(11) 0.0025(12) C6 0.0452(17) 0.0254(14) 0.0126(13) 0.0029(11) 0.0040(11) -0.0014(13) C7 0.0460(17) 0.0221(13) 0.0187(14) -0.0031(11) 0.0019(12) 0.0004(13) C8 0.0400(16) 0.0280(14) 0.0164(14) 0.0007(12) 0.0006(11) 0.0023(13) C9 0.0504(18) 0.0279(14) 0.0150(14) 0.0024(12) 0.0061(12) -0.0005(13) C10 0.0475(17) 0.0226(13) 0.0168(14) 0.0004(11) 0.0041(12) -0.0030(12) C11 0.0457(17) 0.0304(14) 0.0124(13) -0.0038(11) 0.0050(12) 0.0030(13) C12 0.0576(19) 0.0419(17) 0.0152(14) -0.0030(13) 0.0007(13) 0.0027(15) C13 0.056(2) 0.0459(17) 0.0209(15) -0.0054(13) 0.0055(13) 0.0060(15) C14 0.071(2) 0.0343(16) 0.0204(15) -0.0076(12) 0.0054(14) 0.0015(15) C15 0.0409(17) 0.0279(14) 0.0115(13) -0.0004(11) 0.0020(11) 0.0011(13) C16 0.0456(17) 0.0287(14) 0.0215(15) -0.0017(12) 0.0057(13) -0.0018(13) C17 0.0500(19) 0.0400(17) 0.0284(16) -0.0053(13) 0.0118(14) 0.0075(15) C18 0.0449(18) 0.0463(18) 0.0283(16) -0.0015(14) 0.0096(13) -0.0047(15) C19 0.0497(18) 0.0384(16) 0.0237(15) -0.0021(13) 0.0083(13) -0.0119(15) C20 0.0473(17) 0.0285(14) 0.0206(14) -0.0030(12) 0.0069(13) -0.0027(14) C21 0.059(2) 0.059(2) 0.049(2) -0.0058(17) 0.0257(17) -0.0033(18) C22 0.071(3) 0.147(4) 0.164(5) 0.099(4) 0.062(3) 0.047(3) C23 0.062(2) 0.081(2) 0.049(2) 0.0067(18) 0.0225(17) -0.0143(19) C24 0.127(4) 0.095(3) 0.078(3) -0.035(2) 0.068(3) -0.036(3) C25 0.0460(17) 0.0268(14) 0.0160(14) 0.0001(12) 0.0012(12) -0.0031(13) C26 0.0433(17) 0.0255(14) 0.0137(13) 0.0028(12) 0.0025(12) -0.0016(14) C27 0.0446(19) 0.0286(15) 0.0286(15) -0.0020(12) 0.0001(13) -0.0044(14) C28 0.0409(17) 0.0373(16) 0.0328(16) -0.0005(14) 0.0005(13) 0.0019(15) C29 0.0493(19) 0.0255(15) 0.0261(15) -0.0003(13) 0.0035(14) 0.0017(14) C30 0.053(2) 0.0284(15) 0.0228(15) -0.0023(12) -0.0004(13) -0.0051(14) C31 0.0427(17) 0.0285(15) 0.0206(14) 0.0013(12) -0.0015(12) 0.0001(14) C32 0.066(2) 0.0448(19) 0.080(2) -0.0188(18) -0.017(2) 0.0230(18) C33 0.0407(16) 0.0287(14) 0.0159(14) -0.0034(11) 0.0018(12) -0.0028(13) C34 0.0415(17) 0.0244(14) 0.0138(14) -0.0051(11) 0.0035(12) -0.0004(13) C35 0.0455(18) 0.0290(14) 0.0188(14) -0.0043(12) 0.0014(12) 0.0016(13) C36 0.0475(18) 0.0300(14) 0.0197(15) -0.0025(12) 0.0089(13) -0.0023(14) C37 0.060(2) 0.0269(14) 0.0141(15) -0.0010(12) 0.0083(14) 0.0049(14) C38 0.0497(19) 0.0393(16) 0.0197(15) 0.0006(12) -0.0012(13) 0.0048(14) C39 0.0451(18) 0.0364(16) 0.0185(15) -0.0038(12) 0.0038(13) -0.0013(14) C40 0.075(2) 0.0489(18) 0.0255(16) 0.0048(14) 0.0190(16) -0.0005(17) C41 0.098(4) 0.116(4) 0.092(3) -0.024(3) -0.019(3) -0.035(3) C42 0.062(2) 0.062(2) 0.047(2) 0.0040(17) 0.0027(17) 0.0001(19) C43 0.096(3) 0.074(3) 0.069(3) 0.004(2) 0.023(2) -0.021(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.243(3) . ? O2 C4 1.242(3) . ? O3 C29 1.377(3) . ? O3 C32 1.404(4) . ? O4 C37 1.377(3) . ? O4 C40 1.424(3) . ? O5 C41 1.235(5) . ? N1 C1 1.358(3) . ? N1 C2 1.467(3) . ? N2 C1 1.368(3) . ? N2 C25 1.454(3) . ? N2 C3 1.457(3) . ? N3 C4 1.355(3) . ? N3 C2 1.444(3) . ? N4 C4 1.369(3) . ? N4 C33 1.454(3) . ? N4 C3 1.474(3) . ? N5 C41 1.310(5) . ? N5 C42 1.430(4) . ? N5 C43 1.455(4) . ? C2 C5 1.518(3) . ? C2 C3 1.581(4) . ? C3 C15 1.517(3) . ? C5 C6 1.384(3) . ? C5 C10 1.395(3) . ? C6 C7 1.392(3) . ? C7 C8 1.392(3) . ? C8 C9 1.392(3) . ? C8 C11 1.532(3) . ? C9 C10 1.378(3) . ? C11 C12 1.529(4) . ? C11 C14 1.534(3) . ? C11 C13 1.535(4) . ? C15 C20 1.387(3) . ? C15 C16 1.395(3) . ? C16 C17 1.378(3) . ? C17 C18 1.392(4) . ? C18 C19 1.384(4) . ? C18 C21 1.533(4) . ? C19 C20 1.390(3) . ? C21 C22 1.508(5) . ? C21 C24 1.534(5) . ? C21 C23 1.534(4) . ? C25 C26 1.528(3) . ? C26 C27 1.376(4) . ? C26 C31 1.394(4) . ? C27 C28 1.400(4) . ? C28 C29 1.386(4) . ? C29 C30 1.382(4) . ? C30 C31 1.377(4) . ? C33 C34 1.519(3) . ? C34 C39 1.384(3) . ? C34 C35 1.387(3) . ? C35 C36 1.397(3) . ? C36 C37 1.374(4) . ? C37 C38 1.385(4) . ? C38 C39 1.388(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C29 O3 C32 117.1(2) . . ? C37 O4 C40 117.2(2) . . ? C1 N1 C2 111.1(2) . . ? C1 N2 C25 121.69(19) . . ? C1 N2 C3 110.4(2) . . ? C25 N2 C3 125.5(2) . . ? C4 N3 C2 111.0(2) . . ? C4 N4 C33 122.2(2) . . ? C4 N4 C3 110.7(2) . . ? C33 N4 C3 125.0(2) . . ? C41 N5 C42 121.2(3) . . ? C41 N5 C43 121.0(3) . . ? C42 N5 C43 117.8(3) . . ? O1 C1 N1 125.8(3) . . ? O1 C1 N2 124.6(2) . . ? N1 C1 N2 109.6(2) . . ? N3 C2 N1 112.86(18) . . ? N3 C2 C5 113.39(19) . . ? N1 C2 C5 112.44(19) . . ? N3 C2 C3 102.01(19) . . ? N1 C2 C3 100.45(18) . . ? C5 C2 C3 114.62(19) . . ? N2 C3 N4 113.34(17) . . ? N2 C3 C15 113.50(19) . . ? N4 C3 C15 112.23(19) . . ? N2 C3 C2 101.59(19) . . ? N4 C3 C2 100.02(18) . . ? C15 C3 C2 115.03(18) . . ? O2 C4 N3 126.0(2) . . ? O2 C4 N4 124.5(2) . . ? N3 C4 N4 109.5(2) . . ? C6 C5 C10 118.3(2) . . ? C6 C5 C2 121.5(2) . . ? C10 C5 C2 120.1(2) . . ? C5 C6 C7 120.8(2) . . ? C8 C7 C6 121.5(2) . . ? C7 C8 C9 116.8(2) . . ? C7 C8 C11 123.6(2) . . ? C9 C8 C11 119.7(2) . . ? C10 C9 C8 122.4(2) . . ? C9 C10 C5 120.3(2) . . ? C12 C11 C14 107.8(2) . . ? C12 C11 C8 109.20(19) . . ? C14 C11 C8 112.16(19) . . ? C12 C11 C13 108.8(2) . . ? C14 C11 C13 109.2(2) . . ? C8 C11 C13 109.6(2) . . ? C20 C15 C16 117.7(2) . . ? C20 C15 C3 120.8(2) . . ? C16 C15 C3 121.2(2) . . ? C17 C16 C15 120.5(2) . . ? C16 C17 C18 122.5(2) . . ? C19 C18 C17 116.6(2) . . ? C19 C18 C21 122.9(2) . . ? C17 C18 C21 120.4(2) . . ? C18 C19 C20 121.7(2) . . ? C15 C20 C19 121.1(2) . . ? C22 C21 C24 113.4(3) . . ? C22 C21 C18 108.9(3) . . ? C24 C21 C18 108.7(3) . . ? C22 C21 C23 107.5(3) . . ? C24 C21 C23 106.1(3) . . ? C18 C21 C23 112.4(3) . . ? N2 C25 C26 114.5(2) . . ? C27 C26 C31 118.1(2) . . ? C27 C26 C25 119.5(2) . . ? C31 C26 C25 122.4(2) . . ? C26 C27 C28 122.0(3) . . ? C29 C28 C27 118.6(3) . . ? O3 C29 C30 115.6(3) . . ? O3 C29 C28 124.4(3) . . ? C30 C29 C28 120.0(2) . . ? C31 C30 C29 120.5(3) . . ? C30 C31 C26 120.8(3) . . ? N4 C33 C34 114.0(2) . . ? C39 C34 C35 118.0(2) . . ? C39 C34 C33 120.0(2) . . ? C35 C34 C33 122.0(2) . . ? C34 C35 C36 121.1(3) . . ? C37 C36 C35 119.8(3) . . ? C36 C37 O4 124.9(3) . . ? C36 C37 C38 119.9(2) . . ? O4 C37 C38 115.3(3) . . ? C37 C38 C39 119.8(3) . . ? C34 C39 C38 121.4(2) . . ? O5 C41 N5 125.1(5) . . ? _diffrn_measured_fraction_theta_max 0.894 _diffrn_reflns_theta_full 56.38 _diffrn_measured_fraction_theta_full 0.894 _refine_diff_density_max 0.436 _refine_diff_density_min -0.350 _refine_diff_density_rms 0.045