data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 loop_ _publ_author_name 'Uli Kazmaier' 'Christina Hebach' _publ_contact_author_name 'Prof Uli Kazmaier' _publ_contact_author_address ; Institut fuer Organische Chemie Universitaet des Ssaarlandes Im Stadtwald, Geb. 23 66123 Saarbrücken GERMANY ; _publ_contact_author_email U.KAZMAIER@MX.UNI-SAARLAND.DE _publ_section_title ; Via Ugi reaction to conformational fixed cyclic peptides ; data_shelxs1891 _database_code_CSD 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