Electronic Supplementary Material for Organic & Biomolecular Chemistry This journal is © The Royal Society of Chemistry 2004 data_global _journal_coden_Cambridge 177 loop_ _publ_author_name 'Uli Kazmaier' 'Christina Hebach' 'Volker Huch' 'Sabine Maier' 'Heike Mues' 'Anja Watzke' _publ_contact_author_name 'ProfD Uli Kazmaier' _publ_contact_author_address ; Organic Chemistry Universitaet des Saarlandes Geb. 23.2 Postfach 151150 Saarbruecken 66041 GERMANY ; _publ_contact_author_email U.KAZMAIER@MX.UNI-SAARLAND.DE _publ_requested_journal 'Organic & Biomolecular Chemistry' _publ_section_title ; A Straightforward Approach towards Cyclic Peptides via Ring Closing Metathesis - Scope and Limitations ; data_shelxs1891 _database_code_depnum_ccdc_archive 'CCDC 197619' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H35 N3 O7' _chemical_formula_weight 501.57 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 P2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 10.131(2) _cell_length_b 20.904(4) _cell_length_c 12.459(2) _cell_angle_alpha 90.00 _cell_angle_beta 92.53(3) _cell_angle_gamma 90.00 _cell_volume 2636.0(8) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.264 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1072 _exptl_absorpt_coefficient_mu 0.092 _exptl_absorpt_correction_type N/A _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Stoe IPDS' _diffrn_measurement_method 'Image Plate' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16604 _diffrn_reflns_av_R_equivalents 0.0593 _diffrn_reflns_av_sigmaI/netI 0.0536 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.95 _diffrn_reflns_theta_max 24.31 _reflns_number_total 8015 _reflns_number_gt 6922 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0491P)^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 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 -0.4(6) _refine_ls_number_reflns 8015 _refine_ls_number_parameters 649 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0439 _refine_ls_R_factor_gt 0.0359 _refine_ls_wR_factor_ref 0.0883 _refine_ls_wR_factor_gt 0.0845 _refine_ls_goodness_of_fit_ref 1.008 _refine_ls_restrained_S_all 1.008 _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 0.33328(14) 0.80333(7) 0.28104(11) 0.0382(3) Uani 1 1 d . . . N1 N 0.23948(15) 0.83342(7) 0.43639(13) 0.0332(4) Uani 1 1 d . . . C1 C 0.26971(19) 0.84269(9) 0.33258(16) 0.0325(4) Uani 1 1 d . . . C2 C 0.21839(19) 0.90267(10) 0.27237(17) 0.0368(5) Uani 1 1 d . . . H2 H 0.2250 0.9408 0.3180 0.044 Uiso 1 1 calc R . . N2 N 0.29043(16) 0.91077(8) 0.17390(13) 0.0381(4) Uani 1 1 d . . . C3 C 0.2249(2) 0.87993(11) 0.08028(18) 0.0450(5) Uani 1 1 d . . . H3A H 0.2779 0.8451 0.0541 0.054 Uiso 1 1 calc R . . H3B H 0.2079 0.9104 0.0226 0.054 Uiso 1 1 calc R . . C4 C 0.0962(2) 0.85524(13) 0.12375(19) 0.0516(6) Uani 1 1 d . . . H4A H 0.0231 0.8625 0.0724 0.062 Uiso 1 1 calc R . . H4B H 0.1023 0.8098 0.1388 0.062 Uiso 1 1 calc R . . C5 C 0.0774(2) 0.89269(12) 0.22607(18) 0.0475(5) Uani 1 1 d . . . H5A H 0.0251 0.8686 0.2754 0.057 Uiso 1 1 calc R . . H5B H 0.0344 0.9333 0.2107 0.057 Uiso 1 1 calc R . . C6 C 0.4183(2) 0.92857(10) 0.18083(18) 0.0423(5) Uani 1 1 d . . . O2 O 0.47523(16) 0.94750(8) 0.26278(14) 0.0525(4) Uani 1 1 d . . . O3 O 0.47344(15) 0.92456(9) 0.08329(13) 0.0565(5) Uani 1 1 d . . . C7 C 0.6124(2) 0.94066(14) 0.0826(2) 0.0602(7) Uani 1 1 d . . . H7A H 0.6294 0.9777 0.1280 0.072 Uiso 1 1 calc R . . H7B H 0.6349 0.9518 0.0101 0.072 Uiso 1 1 calc R . . C8 C 0.6970(2) 0.88674(14) 0.1216(2) 0.0552(6) Uani 1 1 d . . . H8 H 0.7875 0.8944 0.1282 0.066 Uiso 1 1 calc R . . C9 C 0.6571(3) 0.82955(13) 0.1476(2) 0.0560(6) Uani 1 1 d . . . H9 H 0.5672 0.8209 0.1397 0.067 Uiso 1 1 calc R . . C10 C 0.7452(3) 0.77746(13) 0.1889(2) 0.0654(7) Uani 1 1 d . . . H10A H 0.7479 0.7433 0.1364 0.079 Uiso 1 1 calc R . . H10B H 0.8342 0.7937 0.2016 0.079 Uiso 1 1 calc R . . O4 O 0.69481(18) 0.75299(8) 0.28921(15) 0.0647(5) Uani 1 1 d . . . O5 O 0.7932(2) 0.83409(11) 0.37630(17) 0.0810(6) Uani 1 1 d . . . C11 C 0.7212(2) 0.78889(13) 0.3758(2) 0.0549(6) Uani 1 1 d . . . C12 C 0.6477(2) 0.76600(15) 0.4717(2) 0.0635(7) Uani 1 1 d . . . H12A H 0.6731 0.7223 0.4888 0.076 Uiso 1 1 calc R . . H12B H 0.6710 0.7925 0.5335 0.076 Uiso 1 1 calc R . . N3 N 0.50624(18) 0.76906(10) 0.44863(15) 0.0522(5) Uani 1 1 d . . . H3 H 0.4771 0.7728 0.3830 0.063 Uiso 1 1 calc R . . C13 C 0.4189(2) 0.76618(10) 0.52759(17) 0.0433(5) Uani 1 1 d . . . O6 O 0.45322(18) 0.75743(9) 0.62156(13) 0.0626(5) Uani 1 1 d . . . C14 C 0.2730(2) 0.77187(10) 0.49158(17) 0.0391(5) Uani 1 1 d . . . H14 H 0.2251 0.7728 0.5582 0.047 Uiso 1 1 calc R . . C15 C 0.2222(2) 0.71151(11) 0.43140(19) 0.0470(5) Uani 1 1 d . . . H15 H 0.2728 0.7060 0.3668 0.056 Uiso 1 1 calc R . . C16 C 0.0771(3) 0.71648(13) 0.3982(2) 0.0656(7) Uani 1 1 d . . . H16A H 0.0631 0.7530 0.3524 0.098 Uiso 1 1 calc R . . H16B H 0.0263 0.7212 0.4610 0.098 Uiso 1 1 calc R . . H16C H 0.0498 0.6784 0.3602 0.098 Uiso 1 1 calc R . . C17 C 0.2446(3) 0.65304(13) 0.5037(3) 0.0785(9) Uani 1 1 d . . . H17A H 0.3368 0.6497 0.5244 0.118 Uiso 1 1 calc R . . H17B H 0.2168 0.6152 0.4654 0.118 Uiso 1 1 calc R . . H17C H 0.1943 0.6576 0.5668 0.118 Uiso 1 1 calc R . . C18 C 0.18274(18) 0.88410(10) 0.50569(16) 0.0373(5) Uani 1 1 d . . . H18 H 0.1744 0.9229 0.4618 0.045 Uiso 1 1 calc R . . C19 C 0.0437(2) 0.86760(13) 0.5411(2) 0.0562(6) Uani 1 1 d . . . H19A H -0.0126 0.8586 0.4790 0.084 Uiso 1 1 calc R . . H19B H 0.0087 0.9032 0.5795 0.084 Uiso 1 1 calc R . . H19C H 0.0481 0.8307 0.5871 0.084 Uiso 1 1 calc R . . C20 C 0.2809(2) 0.89912(9) 0.59805(16) 0.0357(5) Uani 1 1 d . . . C21 C 0.4033(2) 0.92413(10) 0.57054(17) 0.0393(5) Uani 1 1 d . . . H21 H 0.4209 0.9313 0.4989 0.047 Uiso 1 1 calc R . . C22 C 0.4973(2) 0.93806(11) 0.65046(19) 0.0478(6) Uani 1 1 d . . . C23 C 0.4707(3) 0.92803(13) 0.7578(2) 0.0573(7) Uani 1 1 d . . . H23 H 0.5341 0.9380 0.8115 0.069 Uiso 1 1 calc R . . C24 C 0.3517(3) 0.90366(14) 0.78433(19) 0.0602(7) Uani 1 1 d . . . H24 H 0.3349 0.8965 0.8561 0.072 Uiso 1 1 calc R . . C25 C 0.2554(2) 0.88939(12) 0.70558(18) 0.0486(6) Uani 1 1 d . . . H25 H 0.1740 0.8734 0.7246 0.058 Uiso 1 1 calc R . . O7 O 0.61967(17) 0.96259(10) 0.63152(17) 0.0734(6) Uani 1 1 d . . . C26 C 0.6543(3) 0.96986(18) 0.5220(3) 0.0859(10) Uani 1 1 d . . . H26A H 0.7418 0.9872 0.5197 0.129 Uiso 1 1 calc R . . H26B H 0.5928 0.9983 0.4857 0.129 Uiso 1 1 calc R . . H26C H 0.6515 0.9289 0.4871 0.129 Uiso 1 1 calc R . . N4 N 0.75578(16) 0.64133(8) -0.15579(12) 0.0332(4) Uani 1 1 d . . . C27 C 0.79215(18) 0.62622(10) -0.05292(15) 0.0334(4) Uani 1 1 d . . . O8 O 0.85633(14) 0.66314(7) 0.00653(11) 0.0405(3) Uani 1 1 d . . . C28 C 0.74899(19) 0.56214(10) -0.00567(16) 0.0369(5) Uani 1 1 d . . . H28 H 0.7519 0.5280 -0.0593 0.044 Uiso 1 1 calc R . . N5 N 0.83048(17) 0.54636(9) 0.08911(13) 0.0397(4) Uani 1 1 d . . . C29 C 0.7739(2) 0.56737(12) 0.18948(17) 0.0472(6) Uani 1 1 d . . . H29A H 0.8277 0.6005 0.2239 0.057 Uiso 1 1 calc R . . H29B H 0.7662 0.5318 0.2389 0.057 Uiso 1 1 calc R . . C30 C 0.6391(2) 0.59295(13) 0.15442(19) 0.0547(6) Uani 1 1 d . . . H30A H 0.6396 0.6393 0.1532 0.066 Uiso 1 1 calc R . . H30B H 0.5727 0.5786 0.2027 0.066 Uiso 1 1 calc R . . C31 C 0.6115(2) 0.56616(12) 0.04183(17) 0.0472(5) Uani 1 1 d . . . H31A H 0.5539 0.5944 -0.0005 0.057 Uiso 1 1 calc R . . H31B H 0.5709 0.5242 0.0448 0.057 Uiso 1 1 calc R . . C32 C 0.9542(2) 0.52499(11) 0.07796(18) 0.0454(5) Uani 1 1 d . . . O9 O 1.00312(17) 0.51186(9) -0.00723(15) 0.0604(4) Uani 1 1 d . . . O10 O 1.01642(16) 0.51938(9) 0.17634(13) 0.0604(5) Uani 1 1 d . . . C33 C 1.1557(2) 0.50641(15) 0.1742(3) 0.0725(8) Uani 1 1 d . . . H33A H 1.1710 0.4751 0.1187 0.087 Uiso 1 1 calc R . . H33B H 1.1858 0.4882 0.2426 0.087 Uiso 1 1 calc R . . C34 C 1.2332(3) 0.56462(14) 0.1534(2) 0.0666(8) Uani 1 1 d . . . H34 H 1.3237 0.5591 0.1477 0.080 Uiso 1 1 calc R . . C35 C 1.1890(3) 0.62294(13) 0.1421(2) 0.0599(7) Uani 1 1 d . . . H35 H 1.0996 0.6299 0.1515 0.072 Uiso 1 1 calc R . . C36 C 1.2711(3) 0.67885(14) 0.1154(2) 0.0718(8) Uani 1 1 d . . . H36A H 1.2741 0.7088 0.1749 0.086 Uiso 1 1 calc R . . H36B H 1.3607 0.6650 0.1034 0.086 Uiso 1 1 calc R . . O11 O 1.21532(18) 0.71034(9) 0.01850(15) 0.0668(5) Uani 1 1 d . . . C37 C 1.2394(2) 0.68327(14) -0.0751(2) 0.0571(7) Uani 1 1 d . . . O12 O 1.3118(2) 0.63812(12) -0.08522(18) 0.0852(6) Uani 1 1 d . . . C38 C 1.1624(2) 0.71460(15) -0.1657(2) 0.0676(8) Uani 1 1 d . . . H38A H 1.1844 0.7597 -0.1685 0.081 Uiso 1 1 calc R . . H38B H 1.1846 0.6952 -0.2333 0.081 Uiso 1 1 calc R . . N6 N 1.02184(18) 0.70697(10) -0.14961(16) 0.0534(5) Uani 1 1 d . . . H6 H 0.9959 0.6985 -0.0864 0.064 Uiso 1 1 calc R . . C39 C 0.9323(2) 0.71287(10) -0.23110(18) 0.0450(5) Uani 1 1 d . . . O13 O 0.96245(19) 0.72623(9) -0.32267(14) 0.0670(5) Uani 1 1 d . . . C40 C 0.7865(2) 0.70507(10) -0.20221(16) 0.0399(5) Uani 1 1 d . . . H40 H 0.7356 0.7070 -0.2709 0.048 Uiso 1 1 calc R . . C41 C 0.7382(2) 0.76276(11) -0.13620(19) 0.0485(6) Uani 1 1 d . . . H41 H 0.7898 0.7642 -0.0679 0.058 Uiso 1 1 calc R . . C42 C 0.5924(2) 0.75694(13) -0.1121(2) 0.0605(7) Uani 1 1 d . . . H42A H 0.5787 0.7185 -0.0719 0.091 Uiso 1 1 calc R . . H42B H 0.5403 0.7554 -0.1783 0.091 Uiso 1 1 calc R . . H42C H 0.5664 0.7933 -0.0708 0.091 Uiso 1 1 calc R . . C43 C 0.7636(4) 0.82435(13) -0.1980(3) 0.0809(9) Uani 1 1 d . . . H43A H 0.8558 0.8272 -0.2123 0.121 Uiso 1 1 calc R . . H43B H 0.7386 0.8605 -0.1559 0.121 Uiso 1 1 calc R . . H43C H 0.7124 0.8240 -0.2647 0.121 Uiso 1 1 calc R . . C44 C 0.6860(2) 0.59582(10) -0.23113(15) 0.0353(5) Uani 1 1 d . . . H44 H 0.6803 0.5552 -0.1924 0.042 Uiso 1 1 calc R . . C45 C 0.5455(2) 0.61607(13) -0.25878(18) 0.0500(6) Uani 1 1 d . . . H45A H 0.5000 0.6231 -0.1938 0.075 Uiso 1 1 calc R . . H45B H 0.5013 0.5831 -0.3002 0.075 Uiso 1 1 calc R . . H45C H 0.5458 0.6549 -0.2998 0.075 Uiso 1 1 calc R . . C46 C 0.7701(2) 0.58284(9) -0.32744(16) 0.0359(5) Uani 1 1 d . . . C47 C 0.7194(2) 0.58654(12) -0.43199(17) 0.0510(6) Uani 1 1 d . . . H47 H 0.6325 0.5996 -0.4453 0.061 Uiso 1 1 calc R . . C48 C 0.7964(3) 0.57103(15) -0.51699(19) 0.0670(8) Uani 1 1 d . . . H48 H 0.7609 0.5744 -0.5869 0.080 Uiso 1 1 calc R . . C49 C 0.9233(3) 0.55086(14) -0.5003(2) 0.0644(7) Uani 1 1 d . . . H49 H 0.9738 0.5400 -0.5581 0.077 Uiso 1 1 calc R . . C50 C 0.9768(2) 0.54673(11) -0.3960(2) 0.0513(6) Uani 1 1 d . . . C51 C 0.9006(2) 0.56261(10) -0.31022(17) 0.0401(5) Uani 1 1 d . . . H51 H 0.9368 0.5597 -0.2405 0.048 Uiso 1 1 calc R . . O14 O 1.10394(18) 0.52477(9) -0.38655(18) 0.0727(5) Uani 1 1 d . . . C52 C 1.1726(3) 0.53041(18) -0.2849(3) 0.0818(10) Uani 1 1 d . . . H52A H 1.2603 0.5136 -0.2895 0.123 Uiso 1 1 calc R . . H52B H 1.1264 0.5068 -0.2321 0.123 Uiso 1 1 calc R . . H52C H 1.1774 0.5747 -0.2644 0.123 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 0.0449(8) 0.0365(8) 0.0329(8) 0.0000(6) -0.0010(6) 0.0039(6) N1 0.0378(9) 0.0312(9) 0.0304(9) 0.0018(7) 0.0002(7) -0.0018(7) C1 0.0332(10) 0.0320(10) 0.0318(11) 0.0018(9) -0.0029(8) -0.0050(9) C2 0.0411(11) 0.0323(11) 0.0372(12) 0.0054(9) 0.0030(9) 0.0014(9) N2 0.0364(9) 0.0433(10) 0.0343(10) 0.0095(8) -0.0026(7) -0.0035(8) C3 0.0467(12) 0.0497(13) 0.0379(12) 0.0065(10) -0.0048(10) -0.0020(10) C4 0.0389(12) 0.0632(15) 0.0517(14) 0.0015(12) -0.0098(11) -0.0038(11) C5 0.0400(12) 0.0536(13) 0.0485(13) 0.0114(11) -0.0020(10) 0.0059(10) C6 0.0414(12) 0.0430(12) 0.0420(13) 0.0123(11) -0.0036(10) 0.0002(10) O2 0.0489(9) 0.0534(10) 0.0542(10) -0.0001(8) -0.0085(8) -0.0069(8) O3 0.0404(8) 0.0858(13) 0.0433(9) 0.0186(9) 0.0008(7) -0.0099(8) C7 0.0408(13) 0.0860(19) 0.0540(15) 0.0183(14) 0.0026(11) -0.0161(13) C8 0.0416(12) 0.0736(17) 0.0502(14) -0.0035(13) 0.0003(10) -0.0095(13) C9 0.0527(14) 0.0710(17) 0.0442(14) -0.0058(13) 0.0006(11) -0.0064(13) C10 0.0734(17) 0.0634(17) 0.0604(17) -0.0099(14) 0.0133(13) 0.0006(14) O4 0.0723(11) 0.0534(10) 0.0684(12) -0.0030(10) 0.0022(9) -0.0034(9) O5 0.0653(12) 0.0954(16) 0.0803(14) -0.0071(12) -0.0178(10) -0.0214(12) C11 0.0400(13) 0.0619(16) 0.0613(16) 0.0007(13) -0.0158(11) 0.0067(12) C12 0.0519(14) 0.0801(18) 0.0567(16) 0.0103(14) -0.0179(12) 0.0095(14) N3 0.0474(11) 0.0709(13) 0.0371(10) 0.0059(10) -0.0102(9) 0.0063(10) C13 0.0616(14) 0.0328(11) 0.0347(13) 0.0038(9) -0.0071(11) 0.0039(10) O6 0.0802(12) 0.0667(11) 0.0395(10) 0.0117(8) -0.0151(8) 0.0117(9) C14 0.0516(12) 0.0347(11) 0.0309(11) 0.0040(9) 0.0009(9) -0.0028(10) C15 0.0608(14) 0.0365(11) 0.0437(13) 0.0037(10) 0.0025(10) -0.0097(11) C16 0.0668(17) 0.0576(16) 0.0714(18) -0.0024(14) -0.0068(14) -0.0228(14) C17 0.116(3) 0.0368(14) 0.082(2) 0.0146(14) -0.0092(18) -0.0109(15) C18 0.0353(11) 0.0398(11) 0.0369(11) -0.0010(9) 0.0028(9) 0.0001(9) C19 0.0402(13) 0.0713(17) 0.0573(15) -0.0070(13) 0.0046(11) -0.0054(12) C20 0.0429(11) 0.0324(11) 0.0318(11) -0.0022(9) 0.0018(9) 0.0017(9) C21 0.0448(12) 0.0416(12) 0.0312(11) 0.0024(9) -0.0010(9) -0.0049(9) C22 0.0457(13) 0.0451(12) 0.0518(15) -0.0058(11) -0.0093(11) -0.0034(10) C23 0.0616(16) 0.0658(16) 0.0431(14) -0.0118(12) -0.0140(12) 0.0034(13) C24 0.0766(18) 0.0754(18) 0.0285(12) -0.0037(12) 0.0009(12) 0.0089(15) C25 0.0526(14) 0.0540(13) 0.0399(13) -0.0008(11) 0.0103(11) 0.0016(11) O7 0.0514(11) 0.0917(15) 0.0757(13) -0.0041(11) -0.0139(9) -0.0261(10) C26 0.0612(18) 0.110(3) 0.087(2) 0.001(2) 0.0093(16) -0.0380(18) N4 0.0403(9) 0.0333(9) 0.0259(9) 0.0013(7) -0.0009(7) 0.0004(7) C27 0.0322(10) 0.0415(11) 0.0264(10) -0.0010(9) -0.0006(8) 0.0059(9) O8 0.0470(8) 0.0447(8) 0.0293(7) -0.0015(7) -0.0045(6) -0.0039(7) C28 0.0417(11) 0.0418(11) 0.0268(10) 0.0038(9) -0.0055(8) 0.0002(9) N5 0.0418(10) 0.0489(10) 0.0278(9) 0.0035(8) -0.0044(7) 0.0055(8) C29 0.0544(14) 0.0590(14) 0.0282(11) -0.0006(10) 0.0003(10) -0.0070(11) C30 0.0486(14) 0.0639(15) 0.0521(15) 0.0012(13) 0.0089(11) -0.0014(12) C31 0.0406(12) 0.0589(14) 0.0418(12) 0.0099(11) -0.0033(10) -0.0037(10) C32 0.0489(14) 0.0450(13) 0.0417(14) 0.0059(11) -0.0064(11) 0.0030(11) O9 0.0565(9) 0.0707(12) 0.0542(11) -0.0110(9) 0.0026(8) 0.0113(9) O10 0.0520(9) 0.0781(12) 0.0495(10) 0.0149(9) -0.0159(8) 0.0084(9) C33 0.0511(15) 0.0745(19) 0.089(2) 0.0172(16) -0.0259(14) 0.0169(14) C34 0.0463(14) 0.0718(19) 0.080(2) -0.0035(15) -0.0187(13) 0.0124(13) C35 0.0611(16) 0.0666(18) 0.0509(15) -0.0118(13) -0.0094(12) 0.0121(14) C36 0.0769(19) 0.0682(18) 0.0682(18) -0.0158(15) -0.0214(15) 0.0025(15) O11 0.0767(12) 0.0554(10) 0.0674(12) -0.0131(10) -0.0057(9) 0.0049(9) C37 0.0425(14) 0.0679(17) 0.0614(17) -0.0059(14) 0.0084(12) -0.0135(13) O12 0.0662(12) 0.1039(17) 0.0871(15) -0.0112(13) 0.0203(11) 0.0217(13) C38 0.0578(16) 0.0816(19) 0.0641(17) 0.0094(16) 0.0107(13) -0.0196(15) N6 0.0462(11) 0.0724(13) 0.0418(11) 0.0053(10) 0.0035(9) -0.0107(10) C39 0.0615(14) 0.0350(11) 0.0390(13) 0.0021(10) 0.0075(11) -0.0070(10) O13 0.0843(12) 0.0737(13) 0.0436(10) 0.0139(9) 0.0107(9) -0.0161(10) C40 0.0524(13) 0.0354(11) 0.0313(11) 0.0047(9) -0.0056(9) 0.0017(10) C41 0.0640(14) 0.0381(12) 0.0423(13) -0.0037(10) -0.0104(10) 0.0065(11) C42 0.0636(16) 0.0586(16) 0.0583(16) -0.0132(13) -0.0063(12) 0.0177(13) C43 0.116(3) 0.0374(14) 0.089(2) 0.0068(15) 0.0027(19) 0.0040(15) C44 0.0412(11) 0.0367(11) 0.0274(10) 0.0004(9) -0.0045(8) -0.0015(9) C45 0.0414(12) 0.0672(15) 0.0407(12) -0.0036(12) -0.0059(10) 0.0024(11) C46 0.0454(12) 0.0301(10) 0.0322(11) 0.0010(9) 0.0005(9) -0.0050(9) C47 0.0543(14) 0.0656(15) 0.0327(12) -0.0068(11) -0.0028(10) -0.0043(12) C48 0.082(2) 0.089(2) 0.0299(13) -0.0104(13) 0.0058(13) -0.0089(17) C49 0.084(2) 0.0628(16) 0.0481(15) -0.0166(13) 0.0270(14) -0.0110(15) C50 0.0517(14) 0.0370(12) 0.0667(17) -0.0056(12) 0.0184(12) -0.0020(11) C51 0.0486(13) 0.0351(11) 0.0368(12) 0.0016(9) 0.0039(9) -0.0003(9) O14 0.0577(11) 0.0702(12) 0.0924(15) -0.0065(11) 0.0266(10) 0.0083(9) C52 0.0478(16) 0.096(2) 0.102(3) 0.025(2) 0.0118(16) 0.0056(15) _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 1.241(2) . ? N1 C1 1.356(3) . ? N1 C14 1.491(3) . ? N1 C18 1.497(3) . ? C1 C2 1.540(3) . ? C2 N2 1.465(3) . ? C2 C5 1.531(3) . ? N2 C6 1.346(3) . ? N2 C3 1.466(3) . ? C3 C4 1.523(3) . ? C4 C5 1.515(4) . ? C6 O2 1.217(3) . ? C6 O3 1.363(3) . ? O3 C7 1.447(3) . ? C7 C8 1.485(4) . ? C8 C9 1.307(4) . ? C9 C10 1.485(4) . ? C10 O4 1.463(3) . ? O4 C11 1.331(3) . ? O5 C11 1.193(3) . ? C11 C12 1.513(4) . ? C12 N3 1.451(3) . ? N3 C13 1.354(3) . ? C13 O6 1.220(2) . ? C13 C14 1.530(3) . ? C14 C15 1.544(3) . ? C15 C16 1.513(4) . ? C15 C17 1.530(3) . ? C18 C20 1.520(3) . ? C18 C19 1.534(3) . ? C20 C25 1.391(3) . ? C20 C21 1.402(3) . ? C21 C22 1.378(3) . ? C22 O7 1.372(3) . ? C22 C23 1.392(4) . ? C23 C24 1.363(4) . ? C24 C25 1.385(4) . ? O7 C26 1.432(4) . ? N4 C27 1.355(2) . ? N4 C40 1.491(3) . ? N4 C44 1.492(3) . ? C27 O8 1.235(2) . ? C27 C28 1.535(3) . ? C28 N5 1.449(2) . ? C28 C31 1.539(3) . ? N5 C32 1.344(3) . ? N5 C29 1.466(3) . ? C29 C30 1.513(3) . ? C30 C31 1.525(3) . ? C32 O9 1.222(3) . ? C32 O10 1.358(3) . ? O10 C33 1.438(3) . ? C33 C34 1.477(4) . ? C34 C35 1.304(4) . ? C35 C36 1.481(4) . ? C36 O11 1.466(3) . ? O11 C37 1.328(3) . ? C37 O12 1.205(3) . ? C37 C38 1.495(4) . ? C38 N6 1.456(3) . ? N6 C39 1.337(3) . ? C39 O13 1.226(3) . ? C39 C40 1.544(3) . ? C40 C41 1.551(3) . ? C41 C42 1.525(4) . ? C41 C43 1.528(4) . ? C44 C45 1.511(3) . ? C44 C46 1.526(3) . ? C46 C47 1.381(3) . ? C46 C51 1.396(3) . ? C47 C48 1.382(4) . ? C48 C49 1.360(4) . ? C49 C50 1.388(4) . ? C50 O14 1.368(3) . ? C50 C51 1.386(3) . ? O14 C52 1.423(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 C1 N1 C14 120.44(16) . . ? C1 N1 C18 123.89(16) . . ? C14 N1 C18 115.47(16) . . ? O1 C1 N1 122.88(17) . . ? O1 C1 C2 117.35(17) . . ? N1 C1 C2 119.69(18) . . ? N2 C2 C5 101.03(16) . . ? N2 C2 C1 109.40(16) . . ? C5 C2 C1 111.22(17) . . ? C6 N2 C2 119.45(17) . . ? C6 N2 C3 124.97(19) . . ? C2 N2 C3 113.00(16) . . ? N2 C3 C4 103.34(18) . . ? C5 C4 C3 105.41(19) . . ? C4 C5 C2 103.72(18) . . ? O2 C6 N2 124.3(2) . . ? O2 C6 O3 124.8(2) . . ? N2 C6 O3 110.93(19) . . ? C6 O3 C7 115.35(18) . . ? O3 C7 C8 111.7(2) . . ? C9 C8 C7 126.5(2) . . ? C8 C9 C10 124.6(2) . . ? O4 C10 C9 109.0(2) . . ? C11 O4 C10 115.4(2) . . ? O5 C11 O4 123.5(3) . . ? O5 C11 C12 124.6(3) . . ? O4 C11 C12 111.9(2) . . ? N3 C12 C11 110.22(19) . . ? C13 N3 C12 121.75(19) . . ? O6 C13 N3 122.4(2) . . ? O6 C13 C14 121.6(2) . . ? N3 C13 C14 115.96(17) . . ? N1 C14 C13 113.57(17) . . ? N1 C14 C15 114.64(16) . . ? C13 C14 C15 112.07(18) . . ? C16 C15 C17 109.5(2) . . ? C16 C15 C14 112.1(2) . . ? C17 C15 C14 109.22(19) . . ? N1 C18 C20 109.13(16) . . ? N1 C18 C19 112.82(18) . . ? C20 C18 C19 114.00(19) . . ? C25 C20 C21 119.6(2) . . ? C25 C20 C18 123.77(19) . . ? C21 C20 C18 116.62(18) . . ? C22 C21 C20 119.5(2) . . ? O7 C22 C21 123.8(2) . . ? O7 C22 C23 115.9(2) . . ? C21 C22 C23 120.3(2) . . ? C24 C23 C22 120.0(2) . . ? C23 C24 C25 120.8(2) . . ? C24 C25 C20 119.7(2) . . ? C22 O7 C26 117.7(2) . . ? C27 N4 C40 121.51(16) . . ? C27 N4 C44 123.21(16) . . ? C40 N4 C44 115.27(15) . . ? O8 C27 N4 122.39(18) . . ? O8 C27 C28 117.83(16) . . ? N4 C27 C28 119.75(17) . . ? N5 C28 C27 110.46(16) . . ? N5 C28 C31 101.05(16) . . ? C27 C28 C31 112.20(17) . . ? C32 N5 C28 119.47(18) . . ? C32 N5 C29 126.14(17) . . ? C28 N5 C29 113.38(17) . . ? N5 C29 C30 103.98(17) . . ? C29 C30 C31 105.20(19) . . ? C30 C31 C28 103.98(17) . . ? O9 C32 N5 125.48(19) . . ? O9 C32 O10 125.1(2) . . ? N5 C32 O10 109.5(2) . . ? C32 O10 C33 114.6(2) . . ? O10 C33 C34 112.2(2) . . ? C35 C34 C33 127.3(3) . . ? C34 C35 C36 124.7(3) . . ? O11 C36 C35 109.8(2) . . ? C37 O11 C36 116.9(2) . . ? O12 C37 O11 124.2(3) . . ? O12 C37 C38 124.3(3) . . ? O11 C37 C38 111.5(2) . . ? N6 C38 C37 109.2(2) . . ? C39 N6 C38 121.3(2) . . ? O13 C39 N6 122.6(2) . . ? O13 C39 C40 121.4(2) . . ? N6 C39 C40 115.9(2) . . ? N4 C40 C39 113.77(17) . . ? N4 C40 C41 114.39(17) . . ? C39 C40 C41 111.65(18) . . ? C42 C41 C43 110.7(2) . . ? C42 C41 C40 111.94(19) . . ? C43 C41 C40 108.9(2) . . ? N4 C44 C45 112.35(17) . . ? N4 C44 C46 110.03(16) . . ? C45 C44 C46 115.08(16) . . ? C47 C46 C51 118.2(2) . . ? C47 C46 C44 122.27(19) . . ? C51 C46 C44 119.40(17) . . ? C46 C47 C48 120.7(2) . . ? C49 C48 C47 121.2(2) . . ? C48 C49 C50 119.3(2) . . ? O14 C50 C51 124.6(2) . . ? O14 C50 C49 115.4(2) . . ? C51 C50 C49 120.0(2) . . ? C50 C51 C46 120.6(2) . . ? C50 O14 C52 118.0(2) . . ? _diffrn_measured_fraction_theta_max 0.963 _diffrn_reflns_theta_full 24.31 _diffrn_measured_fraction_theta_full 0.963 _refine_diff_density_max 0.129 _refine_diff_density_min -0.137 _refine_diff_density_rms 0.027 data_shelxs_27 _database_code_depnum_ccdc_archive 'CCDC 245782' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H33 N3 O7' _chemical_formula_weight 475.53 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 Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 10.967(2) _cell_length_b 14.024(3) _cell_length_c 16.422(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2525.7(8) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.251 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1016 _exptl_absorpt_coefficient_mu 0.092 _exptl_absorpt_correction_type N/A _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Stoe IPDS' _diffrn_measurement_method 'Image Plate' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15951 _diffrn_reflns_av_R_equivalents 0.0881 _diffrn_reflns_av_sigmaI/netI 0.0912 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.91 _diffrn_reflns_theta_max 24.20 _reflns_number_total 3960 _reflns_number_gt 2214 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0996P)^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 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 -1(2) _refine_ls_number_reflns 3960 _refine_ls_number_parameters 307 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1221 _refine_ls_R_factor_gt 0.0647 _refine_ls_wR_factor_ref 0.1809 _refine_ls_wR_factor_gt 0.1538 _refine_ls_goodness_of_fit_ref 0.947 _refine_ls_restrained_S_all 0.947 _refine_ls_shift/su_max 0.085 _refine_ls_shift/su_mean 0.008 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 0.1330(3) 1.0955(3) 0.4314(2) 0.0524(10) Uani 1 1 d . . . O2 O -0.2608(4) 1.1486(5) 0.2752(4) 0.120(2) Uani 1 1 d . . . O3 O -0.1156(4) 1.0978(5) 0.1960(3) 0.112(2) Uani 1 1 d . . . O4 O 0.0211(3) 0.8873(3) -0.0007(2) 0.0582(11) Uani 1 1 d . . . O5 O 0.0183(4) 0.8466(3) 0.1339(2) 0.0664(12) Uani 1 1 d . . . O6 O 0.1816(3) 1.0366(2) 0.1638(2) 0.0436(9) Uani 1 1 d . . . O7 O -0.1057(4) 0.8351(4) 0.4022(3) 0.0817(14) Uani 1 1 d . . . N1 N 0.0532(3) 1.0895(3) 0.3048(3) 0.0420(11) Uani 1 1 d . . . H1 H 0.0655 1.0796 0.2538 0.050 Uiso 1 1 calc R . . N2 N 0.1952(4) 0.8822(3) 0.0679(2) 0.0508(12) Uani 1 1 d . . . H2 H 0.2292 0.8910 0.0213 0.061 Uiso 1 1 calc R . . N3 N 0.2812(4) 0.9727(3) 0.2726(2) 0.0394(10) Uani 1 1 d . . . C1 C 0.2722(4) 1.0619(3) 0.3218(3) 0.0377(12) Uani 1 1 d . . . H1A H 0.3254 1.0512 0.3689 0.045 Uiso 1 1 calc R . . C2 C 0.1466(5) 1.0818(3) 0.3580(3) 0.0411(12) Uani 1 1 d . . . C3 C -0.0681(4) 1.1146(5) 0.3335(3) 0.0567(15) Uani 1 1 d . . . H3A H -0.0650 1.1766 0.3596 0.068 Uiso 1 1 calc R . . H3B H -0.0938 1.0684 0.3740 0.068 Uiso 1 1 calc R . . C4 C -0.1592(6) 1.1173(6) 0.2667(4) 0.081(2) Uani 1 1 d . . . C5 C -0.1919(7) 1.0949(7) 0.1184(6) 0.111(3) Uani 1 1 d . . . H5A H -0.2741 1.0737 0.1305 0.134 Uiso 1 1 calc R . . H5B H -0.1962 1.1579 0.0941 0.134 Uiso 1 1 calc R . . C6 C -0.1335(10) 1.0296(6) 0.0640(6) 0.114(3) Uani 1 1 d . . . H6 H -0.0564 1.0477 0.0463 0.137 Uiso 1 1 calc R . . C7 C -0.1706(8) 0.9525(8) 0.0369(6) 0.116(4) Uani 1 1 d . . . H7 H -0.2538 0.9423 0.0436 0.139 Uiso 1 1 calc R . . C8 C -0.1104(6) 0.8802(6) -0.0010(4) 0.084(2) Uani 1 1 d . . . H8A H -0.1378 0.8773 -0.0571 0.101 Uiso 1 1 calc R . . H8B H -0.1333 0.8207 0.0249 0.101 Uiso 1 1 calc R . . C9 C 0.0748(5) 0.8701(4) 0.0734(3) 0.0542(15) Uani 1 1 d . . . C10 C 0.2683(5) 0.8802(4) 0.1418(3) 0.0497(14) Uani 1 1 d . . . H10 H 0.2503 0.8222 0.1729 0.060 Uiso 1 1 calc R . . C11 C 0.4033(5) 0.8822(6) 0.1187(4) 0.072(2) Uani 1 1 d . . . H11A H 0.4224 0.8269 0.0867 0.108 Uiso 1 1 calc R . . H11B H 0.4521 0.8822 0.1673 0.108 Uiso 1 1 calc R . . H11C H 0.4202 0.9387 0.0877 0.108 Uiso 1 1 calc R . . C12 C 0.2390(4) 0.9692(4) 0.1941(3) 0.0408(12) Uani 1 1 d . . . C13 C 0.3226(5) 0.8865(4) 0.3194(3) 0.0459(13) Uani 1 1 d . . . H13 H 0.3213 0.8325 0.2815 0.055 Uiso 1 1 calc R . . C14 C 0.4521(5) 0.8962(5) 0.3498(4) 0.0576(15) Uani 1 1 d . . . H14A H 0.5054 0.9085 0.3046 0.086 Uiso 1 1 calc R . . H14B H 0.4764 0.8382 0.3762 0.086 Uiso 1 1 calc R . . H14C H 0.4568 0.9482 0.3877 0.086 Uiso 1 1 calc R . . C15 C 0.2283(5) 0.8653(4) 0.3859(3) 0.0463(13) Uani 1 1 d . . . C16 C 0.2582(6) 0.8591(4) 0.4683(3) 0.0617(16) Uani 1 1 d . . . H16 H 0.3387 0.8660 0.4851 0.074 Uiso 1 1 calc R . . C17 C 0.1656(7) 0.8425(5) 0.5254(4) 0.0713(19) Uani 1 1 d . . . H17 H 0.1859 0.8367 0.5802 0.086 Uiso 1 1 calc R . . C18 C 0.0465(7) 0.8344(5) 0.5026(4) 0.0693(19) Uani 1 1 d . . . H18 H -0.0140 0.8243 0.5414 0.083 Uiso 1 1 calc R . . C19 C 0.0167(6) 0.8415(4) 0.4202(4) 0.0579(16) Uani 1 1 d . . . C20 C 0.1056(5) 0.8552(4) 0.3618(3) 0.0523(14) Uani 1 1 d . . . H20 H 0.0847 0.8577 0.3069 0.063 Uiso 1 1 calc R . . C21 C -0.1404(6) 0.8397(6) 0.3198(4) 0.084(2) Uani 1 1 d . . . H21A H -0.2274 0.8336 0.3157 0.126 Uiso 1 1 calc R . . H21B H -0.1020 0.7888 0.2903 0.126 Uiso 1 1 calc R . . H21C H -0.1155 0.8998 0.2973 0.126 Uiso 1 1 calc R . . C22 C 0.3242(4) 1.1509(4) 0.2798(3) 0.0436(12) Uani 1 1 d . . . H22 H 0.2751 1.1638 0.2312 0.052 Uiso 1 1 calc R . . C23 C 0.4570(5) 1.1344(5) 0.2526(4) 0.0640(17) Uani 1 1 d . . . H23A H 0.4869 1.1906 0.2258 0.096 Uiso 1 1 calc R . . H23B H 0.4601 1.0814 0.2156 0.096 Uiso 1 1 calc R . . H23C H 0.5067 1.1210 0.2993 0.096 Uiso 1 1 calc R . . C24 C 0.3152(6) 1.2378(4) 0.3363(4) 0.0583(16) Uani 1 1 d . . . H24A H 0.3470 1.2929 0.3090 0.087 Uiso 1 1 calc R . . H24B H 0.3614 1.2262 0.3849 0.087 Uiso 1 1 calc R . . H24C H 0.2313 1.2487 0.3503 0.087 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 0.056(2) 0.066(3) 0.035(2) -0.0053(19) 0.0040(16) 0.0031(19) O2 0.056(3) 0.187(6) 0.116(4) -0.040(5) -0.006(3) 0.025(4) O3 0.067(3) 0.192(6) 0.077(3) -0.057(4) -0.026(3) 0.039(3) O4 0.055(2) 0.083(3) 0.036(2) 0.001(2) -0.0034(18) -0.006(2) O5 0.073(3) 0.084(3) 0.041(2) 0.002(2) 0.002(2) -0.013(2) O6 0.046(2) 0.050(2) 0.0355(19) 0.0024(17) -0.0045(15) 0.0099(17) O7 0.072(3) 0.095(4) 0.078(3) 0.002(3) 0.006(2) -0.028(3) N1 0.035(2) 0.052(3) 0.039(2) -0.009(2) -0.0003(19) 0.0065(19) N2 0.058(3) 0.066(3) 0.029(2) -0.010(2) 0.000(2) 0.007(2) N3 0.047(2) 0.040(2) 0.031(2) 0.001(2) -0.0041(18) 0.011(2) C1 0.039(3) 0.039(3) 0.035(3) 0.000(2) -0.002(2) 0.003(2) C2 0.044(3) 0.033(3) 0.046(3) 0.000(2) 0.001(2) -0.005(2) C3 0.039(3) 0.074(4) 0.057(4) -0.008(3) 0.003(3) -0.003(3) C4 0.041(4) 0.126(6) 0.076(5) -0.027(5) -0.008(3) 0.024(4) C5 0.090(6) 0.119(7) 0.125(7) -0.014(6) -0.034(5) 0.048(5) C6 0.143(8) 0.057(5) 0.142(8) -0.001(6) 0.011(7) -0.016(6) C7 0.072(5) 0.148(9) 0.128(8) -0.061(7) -0.027(5) 0.026(6) C8 0.065(4) 0.139(8) 0.049(4) -0.006(5) -0.006(3) -0.026(5) C9 0.066(4) 0.062(4) 0.034(3) -0.008(3) -0.001(3) -0.001(3) C10 0.063(3) 0.054(4) 0.032(3) -0.006(3) -0.005(2) 0.015(3) C11 0.062(4) 0.108(6) 0.047(4) -0.023(4) -0.011(3) 0.033(4) C12 0.041(3) 0.045(3) 0.037(3) 0.001(3) 0.003(2) 0.001(2) C13 0.060(3) 0.039(3) 0.039(3) 0.004(3) -0.010(2) 0.009(3) C14 0.057(3) 0.063(4) 0.053(3) 0.000(3) -0.013(3) 0.017(3) C15 0.063(4) 0.037(3) 0.040(3) 0.005(2) -0.001(3) -0.002(3) C16 0.088(4) 0.053(4) 0.044(3) 0.002(3) -0.013(3) -0.006(3) C17 0.103(6) 0.078(5) 0.033(3) 0.010(3) -0.001(3) -0.016(4) C18 0.100(5) 0.065(4) 0.043(4) 0.007(3) 0.012(4) -0.022(4) C19 0.064(4) 0.054(4) 0.056(4) 0.004(3) 0.004(3) -0.011(3) C20 0.068(4) 0.053(3) 0.036(3) 0.002(3) -0.005(3) -0.009(3) C21 0.072(4) 0.099(6) 0.081(5) -0.012(4) -0.014(4) -0.017(4) C22 0.043(3) 0.041(3) 0.046(3) 0.000(3) -0.005(2) 0.000(2) C23 0.048(3) 0.067(4) 0.078(4) 0.011(3) 0.015(3) -0.005(3) C24 0.074(4) 0.043(3) 0.058(4) -0.002(3) -0.010(3) -0.016(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C2 1.229(6) . ? O2 C4 1.205(8) . ? O3 C4 1.287(8) . ? O3 C5 1.524(9) . ? O4 C9 1.373(6) . ? O4 C8 1.446(7) . ? O5 C9 1.216(7) . ? O6 C12 1.240(6) . ? O7 C19 1.378(7) . ? O7 C21 1.407(8) . ? N1 C2 1.351(6) . ? N1 C3 1.455(6) . ? N2 C9 1.334(7) . ? N2 C10 1.455(6) . ? N3 C12 1.372(6) . ? N3 C1 1.493(6) . ? N3 C13 1.502(6) . ? C1 C2 1.526(7) . ? C1 C22 1.536(7) . ? C3 C4 1.485(8) . ? C5 C6 1.432(12) . ? C6 C7 1.237(11) . ? C7 C8 1.361(11) . ? C10 C11 1.529(8) . ? C10 C12 1.548(7) . ? C13 C14 1.512(7) . ? C13 C15 1.533(7) . ? C15 C16 1.394(7) . ? C15 C20 1.410(8) . ? C16 C17 1.403(9) . ? C17 C18 1.363(10) . ? C18 C19 1.395(9) . ? C19 C20 1.381(8) . ? C22 C24 1.535(7) . ? C22 C23 1.541(7) . ? 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 C4 O3 C5 123.8(5) . . ? C9 O4 C8 114.8(4) . . ? C19 O7 C21 117.9(5) . . ? C2 N1 C3 120.2(4) . . ? C9 N2 C10 119.1(4) . . ? C12 N3 C1 121.1(4) . . ? C12 N3 C13 123.6(4) . . ? C1 N3 C13 114.7(4) . . ? N3 C1 C2 115.1(4) . . ? N3 C1 C22 114.4(4) . . ? C2 C1 C22 111.2(4) . . ? O1 C2 N1 122.1(5) . . ? O1 C2 C1 121.3(5) . . ? N1 C2 C1 116.5(5) . . ? N1 C3 C4 112.5(5) . . ? O2 C4 O3 121.7(6) . . ? O2 C4 C3 123.1(6) . . ? O3 C4 C3 114.3(5) . . ? C6 C5 O3 107.0(6) . . ? C7 C6 C5 129.6(11) . . ? C6 C7 C8 131.0(10) . . ? C7 C8 O4 115.6(7) . . ? O5 C9 N2 126.4(5) . . ? O5 C9 O4 123.5(5) . . ? N2 C9 O4 110.0(5) . . ? N2 C10 C11 109.0(4) . . ? N2 C10 C12 109.4(4) . . ? C11 C10 C12 108.9(5) . . ? O6 C12 N3 121.4(5) . . ? O6 C12 C10 119.9(4) . . ? N3 C12 C10 118.7(4) . . ? N3 C13 C14 112.3(5) . . ? N3 C13 C15 108.5(4) . . ? C14 C13 C15 114.6(4) . . ? C16 C15 C20 119.4(5) . . ? C16 C15 C13 123.0(5) . . ? C20 C15 C13 117.6(4) . . ? C15 C16 C17 119.2(6) . . ? C18 C17 C16 121.6(6) . . ? C17 C18 C19 119.0(6) . . ? O7 C19 C20 123.2(5) . . ? O7 C19 C18 115.6(6) . . ? C20 C19 C18 121.2(6) . . ? C19 C20 C15 119.5(5) . . ? C1 C22 C24 110.5(4) . . ? C1 C22 C23 111.1(4) . . ? C24 C22 C23 110.9(4) . . ? _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 24.20 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 0.611 _refine_diff_density_min -0.239 _refine_diff_density_rms 0.054 data_shelxs29 _database_code_depnum_ccdc_archive 'CCDC 245783' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H37 N3 O7' _chemical_formula_weight 503.59 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 Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 9.491(2) _cell_length_b 9.730(2) _cell_length_c 28.504(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2632.3(10) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.271 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1080 _exptl_absorpt_coefficient_mu 0.092 _exptl_absorpt_correction_type N/A _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Stoe IPDS' _diffrn_measurement_method 'Image Plate' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16007 _diffrn_reflns_av_R_equivalents 0.0693 _diffrn_reflns_av_sigmaI/netI 0.0604 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 2.21 _diffrn_reflns_theta_max 24.02 _reflns_number_total 3960 _reflns_number_gt 2908 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0326P)^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 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 1.1(11) _refine_ls_number_reflns 3960 _refine_ls_number_parameters 333 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0592 _refine_ls_R_factor_gt 0.0358 _refine_ls_wR_factor_ref 0.0737 _refine_ls_wR_factor_gt 0.0665 _refine_ls_goodness_of_fit_ref 0.948 _refine_ls_restrained_S_all 0.948 _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 O1 O 0.24614(18) 0.11991(18) -0.15767(5) 0.0339(4) Uani 1 1 d . . . O2 O 0.3158(2) -0.19915(19) -0.19218(6) 0.0418(5) Uani 1 1 d . . . O3 O 0.52274(19) -0.13774(18) -0.22728(5) 0.0389(5) Uani 1 1 d . . . O4 O 0.1125(2) 0.1409(2) -0.27600(6) 0.0480(5) Uani 1 1 d . . . O5 O -0.0216(3) -0.0209(3) -0.30986(8) 0.0752(7) Uani 1 1 d . . . O6 O -0.2152(2) 0.0344(2) -0.15131(6) 0.0508(5) Uani 1 1 d . . . O7 O -0.0330(2) -0.0445(2) 0.11449(6) 0.0519(6) Uani 1 1 d . . . N1 N 0.1222(2) -0.00663(19) -0.10464(6) 0.0239(5) Uani 1 1 d . . . N2 N 0.4733(2) -0.0594(2) -0.15525(7) 0.0314(5) Uani 1 1 d . . . H2 H 0.542(3) -0.015(2) -0.1572(8) 0.019(7) Uiso 1 1 d . . . N3 N -0.0267(3) 0.0983(3) -0.19398(7) 0.0423(6) Uani 1 1 d . . . H3 H 0.052(3) 0.125(3) -0.1913(10) 0.048(10) Uiso 1 1 d . . . C1 C 0.2433(3) 0.0257(2) -0.12825(7) 0.0261(6) Uani 1 1 d . . . C2 C 0.3826(3) -0.0438(2) -0.11420(7) 0.0269(6) Uani 1 1 d . . . H2A H 0.3613 -0.1353 -0.1017 0.032 Uiso 1 1 calc R . . C3 C 0.4550(3) 0.0410(2) -0.07534(8) 0.0282(6) Uani 1 1 d . . . H3A H 0.3852 0.0551 -0.0505 0.034 Uiso 1 1 calc R . . C4 C 0.5030(3) 0.1839(3) -0.09164(9) 0.0399(7) Uani 1 1 d . . . H4A H 0.4241 0.2330 -0.1044 0.060 Uiso 1 1 calc R . . H4B H 0.5744 0.1743 -0.1153 0.060 Uiso 1 1 calc R . . H4C H 0.5407 0.2339 -0.0654 0.060 Uiso 1 1 calc R . . C5 C 0.5768(3) -0.0395(3) -0.05381(8) 0.0387(7) Uani 1 1 d . . . H5A H 0.5436 -0.1278 -0.0436 0.058 Uiso 1 1 calc R . . H5B H 0.6137 0.0101 -0.0274 0.058 Uiso 1 1 calc R . . H5C H 0.6496 -0.0516 -0.0768 0.058 Uiso 1 1 calc R . . C6 C 0.4265(3) -0.1375(3) -0.19154(8) 0.0339(6) Uani 1 1 d . . . C7 C 0.4720(3) -0.1953(3) -0.27104(8) 0.0453(8) Uani 1 1 d . . . H7A H 0.4231 -0.2808 -0.2646 0.054 Uiso 1 1 calc R . . H7B H 0.5518 -0.2160 -0.2911 0.054 Uiso 1 1 calc R . . C8 C 0.3750(3) -0.1003(3) -0.29619(8) 0.0473(8) Uani 1 1 d . . . H8 H 0.3421 -0.1295 -0.3253 0.057 Uiso 1 1 calc R . . C9 C 0.3315(3) 0.0192(3) -0.28181(9) 0.0468(8) Uani 1 1 d . . . H9 H 0.3654 0.0502 -0.2531 0.056 Uiso 1 1 calc R . . C10 C 0.2318(3) 0.1107(3) -0.30752(9) 0.0513(8) Uani 1 1 d . . . H10A H 0.2788 0.1953 -0.3165 0.062 Uiso 1 1 calc R . . H10B H 0.1984 0.0655 -0.3357 0.062 Uiso 1 1 calc R . . C11 C 0.0000(3) 0.0592(3) -0.27893(9) 0.0453(7) Uani 1 1 d . . . C12 C -0.1021(3) 0.0879(4) -0.23916(8) 0.0565(9) Uani 1 1 d . . . H12A H -0.1517 0.1732 -0.2453 0.068 Uiso 1 1 calc R . . H12B H -0.1711 0.0146 -0.2374 0.068 Uiso 1 1 calc R . . C13 C -0.0908(3) 0.0687(2) -0.15338(8) 0.0293(6) Uani 1 1 d . . . C14 C -0.0028(3) 0.0843(2) -0.10805(7) 0.0256(6) Uani 1 1 d . . . H14 H -0.0656 0.0516 -0.0831 0.031 Uiso 1 1 calc R . . C15 C 0.0255(3) 0.2364(2) -0.09522(8) 0.0321(6) Uani 1 1 d . . . H15 H 0.0827 0.2779 -0.1201 0.039 Uiso 1 1 calc R . . C16 C 0.1058(4) 0.2484(3) -0.04877(9) 0.0506(8) Uani 1 1 d . . . H16A H 0.1934 0.1995 -0.0511 0.076 Uiso 1 1 calc R . . H16B H 0.0501 0.2096 -0.0240 0.076 Uiso 1 1 calc R . . H16C H 0.1241 0.3434 -0.0422 0.076 Uiso 1 1 calc R . . C17 C -0.1120(3) 0.3154(3) -0.09140(11) 0.0552(8) Uani 1 1 d . . . H17A H -0.1623 0.3092 -0.1205 0.083 Uiso 1 1 calc R . . H17B H -0.0923 0.4101 -0.0846 0.083 Uiso 1 1 calc R . . H17C H -0.1683 0.2769 -0.0667 0.083 Uiso 1 1 calc R . . C18 C 0.0993(3) -0.1397(2) -0.07905(7) 0.0303(6) Uani 1 1 d . . . H18 H 0.1902 -0.1874 -0.0787 0.036 Uiso 1 1 calc R . . C19 C -0.0021(3) -0.2307(3) -0.10684(9) 0.0461(8) Uani 1 1 d . . . H19A H 0.0315 -0.2402 -0.1384 0.069 Uiso 1 1 calc R . . H19B H -0.0939 -0.1893 -0.1072 0.069 Uiso 1 1 calc R . . H19C H -0.0075 -0.3196 -0.0924 0.069 Uiso 1 1 calc R . . C20 C 0.0572(3) -0.1179(2) -0.02764(8) 0.0277(6) Uani 1 1 d . . . C21 C 0.1621(3) -0.0966(2) 0.00646(8) 0.0340(6) Uani 1 1 d . . . H21 H 0.2564 -0.0980 -0.0025 0.041 Uiso 1 1 calc R . . C22 C 0.1280(3) -0.0734(3) 0.05324(9) 0.0397(7) Uani 1 1 d . . . H22 H 0.1994 -0.0604 0.0751 0.048 Uiso 1 1 calc R . . C23 C -0.0120(3) -0.0693(2) 0.06755(8) 0.0346(6) Uani 1 1 d . . . C24 C -0.1173(3) -0.0916(2) 0.03468(8) 0.0337(6) Uani 1 1 d . . . H24 H -0.2115 -0.0895 0.0436 0.040 Uiso 1 1 calc R . . C25 C -0.0805(3) -0.1174(3) -0.01233(7) 0.0315(6) Uani 1 1 d . . . H25 H -0.1518 -0.1347 -0.0339 0.038 Uiso 1 1 calc R . . C26 C -0.1743(3) -0.0230(3) 0.13085(10) 0.0515(8) Uani 1 1 d . . . H26A H -0.1732 -0.0079 0.1641 0.077 Uiso 1 1 calc R . . H26B H -0.2304 -0.1025 0.1239 0.077 Uiso 1 1 calc R . . H26C H -0.2138 0.0559 0.1155 0.077 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 0.0259(11) 0.0445(10) 0.0312(9) 0.0116(8) 0.0005(8) 0.0033(8) O2 0.0367(14) 0.0513(12) 0.0375(10) -0.0052(9) -0.0007(9) -0.0095(10) O3 0.0300(12) 0.0579(12) 0.0288(9) -0.0097(8) 0.0034(8) 0.0038(9) O4 0.0426(15) 0.0669(13) 0.0344(10) -0.0042(9) 0.0006(9) -0.0005(11) O5 0.0766(19) 0.0930(17) 0.0559(13) -0.0262(13) 0.0056(12) -0.0237(14) O6 0.0223(13) 0.0927(16) 0.0374(10) -0.0013(10) -0.0009(8) -0.0083(10) O7 0.0544(16) 0.0678(14) 0.0334(11) -0.0071(9) 0.0032(9) -0.0054(11) N1 0.0189(13) 0.0293(11) 0.0234(9) 0.0030(8) 0.0009(8) 0.0020(9) N2 0.0184(14) 0.0446(14) 0.0311(12) -0.0052(10) 0.0033(10) -0.0052(11) N3 0.0235(18) 0.0784(18) 0.0250(12) 0.0070(11) -0.0055(10) -0.0036(13) C1 0.0244(17) 0.0317(14) 0.0222(12) -0.0023(11) -0.0021(10) 0.0008(11) C2 0.0232(16) 0.0328(14) 0.0249(12) 0.0013(10) 0.0026(10) 0.0006(11) C3 0.0229(16) 0.0360(15) 0.0257(12) -0.0005(11) 0.0006(10) 0.0017(11) C4 0.0388(19) 0.0407(16) 0.0402(15) -0.0031(12) -0.0045(13) -0.0008(13) C5 0.0332(19) 0.0461(17) 0.0366(14) -0.0020(12) -0.0104(11) 0.0061(13) C6 0.0335(19) 0.0394(16) 0.0287(14) -0.0002(12) -0.0013(12) 0.0057(14) C7 0.045(2) 0.0604(18) 0.0302(14) -0.0162(13) 0.0027(14) 0.0053(16) C8 0.048(2) 0.067(2) 0.0268(14) -0.0098(14) 0.0001(13) 0.0021(17) C9 0.046(2) 0.059(2) 0.0352(15) 0.0011(15) -0.0017(13) -0.0024(16) C10 0.046(2) 0.074(2) 0.0333(14) 0.0068(15) 0.0066(14) 0.0015(16) C11 0.041(2) 0.063(2) 0.0314(16) 0.0041(14) -0.0074(13) 0.0018(17) C12 0.036(2) 0.104(3) 0.0289(14) 0.0022(15) -0.0076(13) 0.0057(19) C13 0.0214(17) 0.0393(15) 0.0272(13) -0.0001(11) -0.0006(11) 0.0037(12) C14 0.0187(15) 0.0363(14) 0.0219(12) 0.0034(10) 0.0009(9) 0.0038(11) C15 0.0305(18) 0.0340(15) 0.0319(13) 0.0015(11) 0.0010(12) 0.0006(12) C16 0.058(2) 0.0453(18) 0.0483(16) -0.0162(14) -0.0114(16) 0.0101(16) C17 0.044(2) 0.0481(18) 0.074(2) -0.0022(15) -0.0057(17) 0.0143(15) C18 0.0277(17) 0.0302(15) 0.0331(13) 0.0039(11) 0.0032(11) 0.0008(12) C19 0.049(2) 0.0428(17) 0.0468(16) -0.0095(13) 0.0034(15) -0.0103(15) C20 0.0250(17) 0.0271(14) 0.0310(13) 0.0076(11) 0.0000(11) -0.0008(11) C21 0.0255(17) 0.0373(17) 0.0392(15) 0.0111(12) 0.0003(12) -0.0034(12) C22 0.036(2) 0.0472(18) 0.0357(15) 0.0045(12) -0.0111(13) -0.0091(14) C23 0.040(2) 0.0341(14) 0.0293(14) 0.0056(11) 0.0011(12) -0.0046(13) C24 0.0257(17) 0.0374(17) 0.0379(14) 0.0089(12) 0.0045(12) 0.0009(12) C25 0.0246(18) 0.0414(16) 0.0286(13) 0.0082(12) -0.0029(11) -0.0028(12) C26 0.058(2) 0.0504(19) 0.0462(17) -0.0013(14) 0.0124(14) -0.0031(16) _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 C6 1.210(3) . ? O3 C6 1.368(3) . ? O3 C7 1.450(3) . ? O4 C11 1.334(4) . ? O4 C10 1.475(3) . ? O5 C11 1.194(3) . ? O6 C13 1.229(3) . ? O7 C23 1.374(3) . ? O7 C26 1.435(3) . ? N1 C1 1.368(3) . ? N1 C14 1.484(3) . ? N1 C18 1.502(3) . ? N2 C6 1.358(3) . ? N2 C2 1.461(3) . ? N3 C13 1.339(3) . ? N3 C12 1.476(3) . ? C1 C2 1.538(3) . ? C2 C3 1.543(3) . ? C3 C5 1.525(3) . ? C3 C4 1.535(3) . ? C7 C8 1.488(4) . ? C8 C9 1.300(4) . ? C9 C10 1.492(4) . ? C11 C12 1.517(4) . ? C13 C14 1.546(3) . ? C14 C15 1.548(3) . ? C15 C17 1.519(4) . ? C15 C16 1.532(3) . ? C18 C19 1.528(4) . ? C18 C20 1.533(3) . ? C20 C25 1.378(3) . ? C20 C21 1.407(3) . ? C21 C22 1.391(3) . ? C22 C23 1.390(4) . ? C23 C24 1.387(4) . ? C24 C25 1.407(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 C6 O3 C7 114.8(2) . . ? C11 O4 C10 117.2(2) . . ? C23 O7 C26 118.5(2) . . ? C1 N1 C14 120.18(18) . . ? C1 N1 C18 123.97(19) . . ? C14 N1 C18 115.45(18) . . ? C6 N2 C2 118.4(2) . . ? C13 N3 C12 121.3(3) . . ? O1 C1 N1 121.3(2) . . ? O1 C1 C2 118.8(2) . . ? N1 C1 C2 119.53(19) . . ? N2 C2 C1 110.10(18) . . ? N2 C2 C3 111.6(2) . . ? C1 C2 C3 109.56(18) . . ? C5 C3 C4 111.2(2) . . ? C5 C3 C2 110.58(19) . . ? C4 C3 C2 113.54(19) . . ? O2 C6 N2 124.9(2) . . ? O2 C6 O3 124.6(2) . . ? N2 C6 O3 110.5(2) . . ? O3 C7 C8 112.3(2) . . ? C9 C8 C7 126.9(3) . . ? C8 C9 C10 125.5(3) . . ? O4 C10 C9 107.9(2) . . ? O5 C11 O4 124.9(3) . . ? O5 C11 C12 124.2(3) . . ? O4 C11 C12 110.8(2) . . ? N3 C12 C11 110.8(3) . . ? O6 C13 N3 122.4(2) . . ? O6 C13 C14 120.4(2) . . ? N3 C13 C14 117.1(2) . . ? N1 C14 C13 115.36(18) . . ? N1 C14 C15 114.6(2) . . ? C13 C14 C15 112.66(19) . . ? C17 C15 C16 109.1(2) . . ? C17 C15 C14 110.6(2) . . ? C16 C15 C14 111.3(2) . . ? N1 C18 C19 109.81(19) . . ? N1 C18 C20 112.50(19) . . ? C19 C18 C20 114.3(2) . . ? C25 C20 C21 116.9(2) . . ? C25 C20 C18 123.4(2) . . ? C21 C20 C18 119.8(2) . . ? C22 C21 C20 121.4(2) . . ? C23 C22 C21 120.6(2) . . ? O7 C23 C24 125.5(2) . . ? O7 C23 C22 115.4(2) . . ? C24 C23 C22 119.1(2) . . ? C23 C24 C25 119.4(2) . . ? C20 C25 C24 122.6(2) . . ? _diffrn_measured_fraction_theta_max 0.957 _diffrn_reflns_theta_full 24.02 _diffrn_measured_fraction_theta_full 0.957 _refine_diff_density_max 0.140 _refine_diff_density_min -0.140 _refine_diff_density_rms 0.034