Supplementary Material (ESI) for Perkin Transactions This journal is © The Royal Society of Chemistry 2002 data_global _journal_coden_Cambridge 207 _publ_requested_journal 'Journal of the Chemical Society, Perkin Transactions I' loop_ _publ_author_name _publ_author_address 'Bianca C. Wallfisch' ; Institute of Chemistry, Karl-Franzens-University of Graz, A-8010 Graz, Austria ; 'Ferdinand Belaj' ; Institute of Chemistry, Karl-Franzens-University of Graz, A-8010 Graz, Austria ; 'Curt Wentrup' ; Department of Chemistry, The University of Queensland, Qu-4072, Brisbane, Australia ; 'C. Oliver Kappe' ; Institute of Chemistry, Karl-Franzens-University of Graz, A-8010 Graz, Austria ; 'Gert Kollenz' ; Institute of Chemistry, Karl-Franzens-University of Graz, A-8010 Graz, Austria ; _publ_contact_author_name 'Prof Gert Kollenz' _publ_contact_author_address ; Institute of Chemistry, Karl-Franzens-University of Graz, Schubertstr. 1, A-8010 Graz, Austria ; _publ_contact_author_email 'KOLLENZ@KFUNIGRAZ.AC.AT' _publ_contact_author_fax '43(316)3809835' _publ_contact_author_phone '43(316)3805288' _publ_contact_letter ; Please consider this CIF submission for deposition. The paper will be submitted to the Journal of the Chemical Society, Perkin Transactions I ; _publ_section_title ; Synthesis and Chemical Reactivity of Methoxycarbonyl-1,3-dioxinyl-pivaloylketene - A Persistent alpha-Oxoketene ; data_6(BCW405) _database_code_CSD 175718 _audit_creation_method 'manual edited SHELXL-97 .cif file' _chemical_name_systematic ; 2-(3,3-dimethyl-2-oxo-1-(oxomethylene)butyl)-2,6-di-tert-butyl- -5-methoxycarbonyl-1,3-dioxin-4(2H)-one ; _chemical_name_common ? _chemical_melting_point 378 _chemical_formula_moiety ? _chemical_formula_sum 'C21 H30 O7' _chemical_formula_weight 394.45 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' '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 'P 21 21 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 9.975(2) _cell_length_b 11.266(2) _cell_length_c 19.208(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2158.6(7) _cell_formula_units_Z 4 _cell_measurement_temperature 95(2) _cell_measurement_reflns_used 38 _cell_measurement_theta_min 15.05 _cell_measurement_theta_max 18.32 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.36 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.214 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 848 _exptl_absorpt_coefficient_mu 0.090 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 95(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Stoe 4-circle' _diffrn_measurement_method '\w' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 100 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 1.1 _diffrn_reflns_number 3197 _diffrn_reflns_av_R_equivalents 0.0317 _diffrn_reflns_av_sigmaI/netI 0.0504 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -1 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -1 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.73 _diffrn_reflns_theta_max 26.00 _reflns_number_total 2741 _reflns_number_gt 2477 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'local program' _computing_cell_refinement 'local program' _computing_data_reduction 'local program' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP (Johnson, 1965)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. The H-atoms of the methyl groups were refined with common isotropic displacement parameters for the H-atoms of the same methyl group and idealized geometry with tetrahedral angles, staggered conformation, and C-H distances of 0.98 \%A (AFIX 33 of SHELXL97 for the methyl goups of the tert-butyl groups, AFIX 137 for the hydrogen atoms of the methoxy group). Due to the absence of heavier atoms the absolute structure cannot be determined reliably. (The Flack parameter x for the inverted absolute structure resulted in 1.4(10) instead of -0.5(10).) ; _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^)+(0.0300P)^2^+0.1907P] 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(10) _refine_ls_number_reflns 2741 _refine_ls_number_parameters 264 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0420 _refine_ls_R_factor_gt 0.0359 _refine_ls_wR_factor_ref 0.0850 _refine_ls_wR_factor_gt 0.0809 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.052 _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 0.37942(15) -0.00337(12) 0.05187(7) 0.0172(3) Uani 1 1 d . . . C2 C 0.4491(2) -0.05024(18) 0.11063(10) 0.0153(4) Uani 1 1 d . . . O3 O 0.52736(14) 0.04118(12) 0.14257(7) 0.0166(3) Uani 1 1 d . . . C4 C 0.4631(2) 0.14625(18) 0.15669(10) 0.0171(4) Uani 1 1 d . . . O4 O 0.50984(15) 0.20914(14) 0.20091(7) 0.0242(4) Uani 1 1 d . . . C5 C 0.3466(2) 0.17289(18) 0.11373(10) 0.0169(4) Uani 1 1 d . . . C6 C 0.3141(2) 0.10061(18) 0.05997(11) 0.0173(4) Uani 1 1 d . . . C11 C 0.3468(2) -0.09210(18) 0.16552(10) 0.0150(4) Uani 1 1 d . . . C10 C 0.3799(2) -0.06248(19) 0.23019(10) 0.0180(5) Uani 1 1 d . . . O10 O 0.41146(16) -0.03286(15) 0.28494(7) 0.0262(4) Uani 1 1 d . . . C12 C 0.2174(2) -0.15090(19) 0.14921(11) 0.0186(5) Uani 1 1 d . . . O12 O 0.19481(16) -0.18161(15) 0.08970(8) 0.0271(4) Uani 1 1 d . . . C13 C 0.1112(2) -0.1676(2) 0.20648(11) 0.0218(5) Uani 1 1 d . . . C14 C 0.0714(2) -0.0459(2) 0.23613(13) 0.0308(6) Uani 1 1 d . . . H141 H 0.1501 -0.0081 0.2572 0.045(5) Uiso 1 1 calc R . . H142 H 0.0017 -0.0563 0.2715 0.045(5) Uiso 1 1 calc R . . H143 H 0.0371 0.0045 0.1985 0.045(5) Uiso 1 1 calc R . . C15 C 0.1635(2) -0.2480(2) 0.26487(12) 0.0246(5) Uani 1 1 d . . . H151 H 0.2414 -0.2107 0.2870 0.029(4) Uiso 1 1 calc R . . H152 H 0.1898 -0.3249 0.2453 0.029(4) Uiso 1 1 calc R . . H153 H 0.0928 -0.2599 0.2996 0.029(4) Uiso 1 1 calc R . . C16 C -0.0111(2) -0.2264(3) 0.17376(14) 0.0386(7) Uani 1 1 d . . . H161 H 0.0144 -0.3040 0.1548 0.053(5) Uiso 1 1 calc R . . H162 H -0.0455 -0.1761 0.1362 0.053(5) Uiso 1 1 calc R . . H163 H -0.0807 -0.2370 0.2092 0.053(5) Uiso 1 1 calc R . . C20 C 0.5490(2) -0.14350(19) 0.08300(11) 0.0195(5) Uani 1 1 d . . . C21 C 0.6243(2) -0.1981(2) 0.14438(12) 0.0300(6) Uani 1 1 d . . . H211 H 0.6715 -0.1355 0.1699 0.037(4) Uiso 1 1 calc R . . H212 H 0.6892 -0.2563 0.1271 0.037(4) Uiso 1 1 calc R . . H213 H 0.5604 -0.2375 0.1755 0.037(4) Uiso 1 1 calc R . . C22 C 0.6478(3) -0.0824(2) 0.03350(13) 0.0306(6) Uani 1 1 d . . . H221 H 0.6952 -0.0192 0.0584 0.042(5) Uiso 1 1 calc R . . H222 H 0.5986 -0.0482 -0.0059 0.042(5) Uiso 1 1 calc R . . H223 H 0.7127 -0.1407 0.0163 0.042(5) Uiso 1 1 calc R . . C23 C 0.4753(2) -0.2416(2) 0.04306(12) 0.0277(5) Uani 1 1 d . . . H231 H 0.4113 -0.2809 0.0741 0.045(5) Uiso 1 1 calc R . . H232 H 0.5404 -0.2999 0.0260 0.045(5) Uiso 1 1 calc R . . H233 H 0.4272 -0.2068 0.0036 0.045(5) Uiso 1 1 calc R . . C50 C 0.2734(2) 0.28354(19) 0.13273(11) 0.0205(5) Uani 1 1 d . . . O50 O 0.15980(16) 0.28551(15) 0.15460(9) 0.0336(4) Uani 1 1 d . . . O51 O 0.34962(16) 0.37945(13) 0.12422(8) 0.0247(4) Uani 1 1 d . . . C51 C 0.2928(3) 0.4883(2) 0.15057(14) 0.0319(6) Uani 1 1 d . . . H511 H 0.2098 0.5062 0.1253 0.044(5) Uiso 1 1 calc R . . H512 H 0.3569 0.5532 0.1440 0.044(5) Uiso 1 1 calc R . . H513 H 0.2731 0.4793 0.2003 0.044(5) Uiso 1 1 calc R . . C60 C 0.2113(3) 0.1203(2) 0.00275(11) 0.0263(5) Uani 1 1 d . . . C61 C 0.0732(2) 0.0822(3) 0.03027(14) 0.0371(6) Uani 1 1 d . . . H611 H 0.0057 0.0937 -0.0062 0.039(4) Uiso 1 1 calc R . . H612 H 0.0498 0.1304 0.0710 0.039(4) Uiso 1 1 calc R . . H613 H 0.0760 -0.0017 0.0436 0.039(4) Uiso 1 1 calc R . . C62 C 0.2470(3) 0.0445(3) -0.06046(12) 0.0465(8) Uani 1 1 d . . . H621 H 0.1812 0.0581 -0.0975 0.051(5) Uiso 1 1 calc R . . H622 H 0.2461 -0.0396 -0.0473 0.051(5) Uiso 1 1 calc R . . H623 H 0.3365 0.0661 -0.0772 0.051(5) Uiso 1 1 calc R . . C63 C 0.2069(3) 0.2506(2) -0.01979(14) 0.0414(7) Uani 1 1 d . . . H631 H 0.1414 0.2602 -0.0574 0.057(5) Uiso 1 1 calc R . . H632 H 0.2957 0.2748 -0.0363 0.057(5) Uiso 1 1 calc R . . H633 H 0.1809 0.3001 0.0199 0.057(5) 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 0.0244(8) 0.0171(7) 0.0100(6) -0.0002(6) -0.0014(6) 0.0021(7) C2 0.0156(10) 0.0166(10) 0.0137(9) 0.0007(8) -0.0028(8) -0.0004(9) O3 0.0153(7) 0.0179(7) 0.0165(6) -0.0017(6) 0.0002(6) -0.0003(6) C4 0.0202(10) 0.0154(10) 0.0157(9) -0.0001(9) 0.0041(9) -0.0047(9) O4 0.0305(8) 0.0214(7) 0.0208(7) -0.0046(7) -0.0062(7) -0.0035(7) C5 0.0181(10) 0.0158(10) 0.0168(10) 0.0014(8) 0.0023(9) -0.0008(9) C6 0.0192(11) 0.0183(10) 0.0145(9) 0.0027(9) 0.0012(9) 0.0004(9) C11 0.0177(10) 0.0158(10) 0.0115(9) 0.0007(8) 0.0006(8) 0.0012(9) C10 0.0167(10) 0.0180(10) 0.0192(11) 0.0047(9) 0.0039(9) -0.0009(9) O10 0.0376(10) 0.0288(8) 0.0122(7) -0.0005(7) -0.0009(7) -0.0070(8) C12 0.0194(10) 0.0171(10) 0.0194(10) -0.0009(9) -0.0002(9) 0.0030(9) O12 0.0261(8) 0.0345(9) 0.0207(8) -0.0074(7) -0.0012(7) -0.0063(8) C13 0.0168(10) 0.0249(11) 0.0235(10) 0.0003(10) 0.0046(9) -0.0013(10) C14 0.0283(13) 0.0297(13) 0.0344(12) 0.0055(11) 0.0132(11) 0.0103(11) C15 0.0238(11) 0.0221(11) 0.0278(11) 0.0038(10) 0.0074(9) 0.0014(11) C16 0.0230(12) 0.0551(18) 0.0376(13) 0.0056(13) 0.0017(11) -0.0094(14) C20 0.0211(11) 0.0173(10) 0.0200(10) -0.0017(9) 0.0062(9) 0.0022(10) C21 0.0263(12) 0.0306(12) 0.0333(12) 0.0035(11) 0.0022(11) 0.0140(12) C22 0.0320(13) 0.0245(11) 0.0354(13) 0.0000(11) 0.0169(11) 0.0028(11) C23 0.0324(12) 0.0219(11) 0.0287(12) -0.0069(10) 0.0094(10) 0.0024(11) C50 0.0246(11) 0.0182(11) 0.0188(10) 0.0014(9) -0.0001(9) 0.0023(10) O50 0.0262(9) 0.0272(9) 0.0473(10) -0.0036(8) 0.0127(8) 0.0035(8) O51 0.0304(9) 0.0155(7) 0.0283(8) 0.0004(7) 0.0032(7) 0.0015(7) C51 0.0386(14) 0.0168(11) 0.0403(13) -0.0019(11) 0.0003(12) 0.0046(11) C60 0.0329(12) 0.0269(12) 0.0190(11) 0.0017(10) -0.0112(10) 0.0028(11) C61 0.0268(13) 0.0418(15) 0.0427(14) 0.0063(13) -0.0172(12) -0.0011(12) C62 0.064(2) 0.0554(18) 0.0203(11) -0.0062(14) -0.0183(13) 0.0110(17) C63 0.0500(16) 0.0362(14) 0.0380(15) 0.0132(14) -0.0214(13) 0.0022(14) _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 1.427(2) . yes O1 C6 1.349(2) . yes C2 O3 1.431(2) . yes C2 C11 1.541(3) . yes C2 C20 1.542(3) . yes O3 C4 1.373(2) . yes C4 O4 1.200(2) . yes C4 C5 1.456(3) . yes C5 C6 1.354(3) . yes C5 C50 1.490(3) . yes C6 C60 1.520(3) . ? C11 C10 1.328(3) . yes C11 C12 1.484(3) . yes C10 O10 1.147(3) . yes C12 O12 1.215(3) . yes C12 C13 1.539(3) . yes C13 C16 1.524(3) . ? C13 C15 1.534(3) . ? C13 C14 1.537(3) . ? C14 H141 0.9800 . ? C14 H142 0.9800 . ? C14 H143 0.9800 . ? C15 H151 0.9800 . ? C15 H152 0.9800 . ? C15 H153 0.9800 . ? C16 H161 0.9800 . ? C16 H162 0.9800 . ? C16 H163 0.9800 . ? C20 C21 1.527(3) . ? C20 C22 1.532(3) . ? C20 C23 1.533(3) . ? C21 H211 0.9800 . ? C21 H212 0.9800 . ? C21 H213 0.9800 . ? C22 H221 0.9800 . ? C22 H222 0.9800 . ? C22 H223 0.9800 . ? C23 H231 0.9800 . ? C23 H232 0.9800 . ? C23 H233 0.9800 . ? C50 O50 1.209(3) . yes C50 O51 1.331(3) . yes O51 C51 1.442(3) . yes C51 H511 0.9800 . ? C51 H512 0.9800 . ? C51 H513 0.9800 . ? C60 C62 1.527(3) . ? C60 C63 1.530(3) . ? C60 C61 1.537(4) . ? C61 H611 0.9800 . ? C61 H612 0.9800 . ? C61 H613 0.9800 . ? C62 H621 0.9800 . ? C62 H622 0.9800 . ? C62 H623 0.9800 . ? C63 H631 0.9800 . ? C63 H632 0.9800 . ? C63 H633 0.9800 . ? 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 O1 C2 117.73(16) . . yes O1 C2 O3 109.79(16) . . yes O1 C2 C11 109.39(16) . . ? O3 C2 C11 106.75(15) . . ? O1 C2 C20 107.14(15) . . ? O3 C2 C20 106.58(16) . . ? C11 C2 C20 117.04(17) . . yes C4 O3 C2 116.77(15) . . yes O4 C4 O3 117.85(19) . . yes O4 C4 C5 126.11(19) . . yes O3 C4 C5 115.99(17) . . yes C6 C5 C4 119.95(19) . . yes C6 C5 C50 124.91(19) . . yes C4 C5 C50 115.12(18) . . yes O1 C6 C5 119.61(19) . . yes O1 C6 C60 111.68(18) . . yes C5 C6 C60 128.7(2) . . yes C10 C11 C12 121.70(19) . . yes C10 C11 C2 113.50(18) . . yes C12 C11 C2 124.61(17) . . yes O10 C10 C11 177.1(2) . . yes O12 C12 C11 119.13(19) . . yes O12 C12 C13 120.66(19) . . yes C11 C12 C13 120.15(17) . . yes C16 C13 C15 108.47(19) . . ? C16 C13 C14 109.5(2) . . ? C15 C13 C14 110.14(18) . . ? C16 C13 C12 108.01(18) . . ? C15 C13 C12 111.15(18) . . ? C14 C13 C12 109.51(17) . . ? C13 C14 H141 109.5 . . ? C13 C14 H142 109.5 . . ? H141 C14 H142 109.5 . . ? C13 C14 H143 109.5 . . ? H141 C14 H143 109.5 . . ? H142 C14 H143 109.5 . . ? C13 C15 H151 109.5 . . ? C13 C15 H152 109.5 . . ? H151 C15 H152 109.5 . . ? C13 C15 H153 109.5 . . ? H151 C15 H153 109.5 . . ? H152 C15 H153 109.5 . . ? C13 C16 H161 109.5 . . ? C13 C16 H162 109.5 . . ? H161 C16 H162 109.5 . . ? C13 C16 H163 109.5 . . ? H161 C16 H163 109.5 . . ? H162 C16 H163 109.5 . . ? C21 C20 C22 110.09(19) . . ? C21 C20 C23 109.38(19) . . ? C22 C20 C23 108.76(18) . . ? C21 C20 C2 109.05(17) . . ? C22 C20 C2 108.84(18) . . ? C23 C20 C2 110.70(18) . . ? C20 C21 H211 109.5 . . ? C20 C21 H212 109.5 . . ? H211 C21 H212 109.5 . . ? C20 C21 H213 109.5 . . ? H211 C21 H213 109.5 . . ? H212 C21 H213 109.5 . . ? C20 C22 H221 109.5 . . ? C20 C22 H222 109.5 . . ? H221 C22 H222 109.5 . . ? C20 C22 H223 109.5 . . ? H221 C22 H223 109.5 . . ? H222 C22 H223 109.5 . . ? C20 C23 H231 109.5 . . ? C20 C23 H232 109.5 . . ? H231 C23 H232 109.5 . . ? C20 C23 H233 109.5 . . ? H231 C23 H233 109.5 . . ? H232 C23 H233 109.5 . . ? O50 C50 O51 124.3(2) . . yes O50 C50 C5 124.1(2) . . yes O51 C50 C5 111.67(17) . . yes C50 O51 C51 114.99(17) . . yes O51 C51 H511 109.5 . . ? O51 C51 H512 109.5 . . ? H511 C51 H512 109.5 . . ? O51 C51 H513 109.5 . . ? H511 C51 H513 109.5 . . ? H512 C51 H513 109.5 . . ? C6 C60 C62 109.6(2) . . ? C6 C60 C63 111.4(2) . . ? C62 C60 C63 108.6(2) . . ? C6 C60 C61 108.39(18) . . ? C62 C60 C61 109.0(2) . . ? C63 C60 C61 109.9(2) . . ? C60 C61 H611 109.5 . . ? C60 C61 H612 109.5 . . ? H611 C61 H612 109.5 . . ? C60 C61 H613 109.5 . . ? H611 C61 H613 109.5 . . ? H612 C61 H613 109.5 . . ? C60 C62 H621 109.5 . . ? C60 C62 H622 109.5 . . ? H621 C62 H622 109.5 . . ? C60 C62 H623 109.5 . . ? H621 C62 H623 109.5 . . ? H622 C62 H623 109.5 . . ? C60 C63 H631 109.5 . . ? C60 C63 H632 109.5 . . ? H631 C63 H632 109.5 . . ? C60 C63 H633 109.5 . . ? H631 C63 H633 109.5 . . ? H632 C63 H633 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 O1 C2 O3 -47.0(2) . . . . yes O1 C2 O3 C4 49.8(2) . . . . yes C2 O3 C4 C5 -25.0(2) . . . . yes O3 C4 C5 C6 -5.2(3) . . . . yes C4 C5 C6 O1 8.3(3) . . . . yes C5 C6 O1 C2 19.1(3) . . . . yes C6 O1 C2 C11 69.9(2) . . . . ? C6 O1 C2 C20 -162.32(17) . . . . ? C11 C2 O3 C4 -68.7(2) . . . . ? C20 C2 O3 C4 165.47(16) . . . . ? C2 O3 C4 O4 157.62(18) . . . . ? O4 C4 C5 C6 172.0(2) . . . . ? O4 C4 C5 C50 -6.5(3) . . . . ? O3 C4 C5 C50 176.40(17) . . . . ? C2 O1 C6 C60 -162.19(17) . . . . ? C50 C5 C6 O1 -173.44(18) . . . . ? C4 C5 C6 C60 -170.2(2) . . . . ? C50 C5 C6 C60 8.1(4) . . . . ? O1 C2 C11 C10 -137.29(19) . . . . ? O3 C2 C11 C10 -18.6(2) . . . . yes C20 C2 C11 C10 100.7(2) . . . . ? O1 C2 C11 C12 37.8(3) . . . . ? O3 C2 C11 C12 156.49(18) . . . . yes C20 C2 C11 C12 -84.3(2) . . . . ? C12 C11 C10 O10 -149(5) . . . . ? C2 C11 C10 O10 26(5) . . . . ? C10 C11 C12 O12 -176.3(2) . . . . ? C2 C11 C12 O12 9.0(3) . . . . ? C10 C11 C12 C13 6.3(3) . . . . ? C2 C11 C12 C13 -168.32(19) . . . . ? O12 C12 C13 C16 0.9(3) . . . . ? C11 C12 C13 C16 178.2(2) . . . . yes O12 C12 C13 C15 119.8(2) . . . . ? C11 C12 C13 C15 -62.9(3) . . . . ? O12 C12 C13 C14 -118.3(2) . . . . ? C11 C12 C13 C14 59.0(3) . . . . ? O1 C2 C20 C21 -178.92(17) . . . . yes O3 C2 C20 C21 63.6(2) . . . . ? C11 C2 C20 C21 -55.7(2) . . . . ? O1 C2 C20 C22 61.0(2) . . . . ? O3 C2 C20 C22 -56.5(2) . . . . ? C11 C2 C20 C22 -175.84(18) . . . . ? O1 C2 C20 C23 -58.5(2) . . . . ? O3 C2 C20 C23 -176.02(16) . . . . ? C11 C2 C20 C23 64.7(2) . . . . ? C6 C5 C50 O50 66.7(3) . . . . ? C4 C5 C50 O50 -115.0(2) . . . . ? C6 C5 C50 O51 -114.8(2) . . . . ? C4 C5 C50 O51 63.5(2) . . . . yes O50 C50 O51 C51 6.8(3) . . . . yes C5 C50 O51 C51 -171.74(19) . . . . ? O1 C6 C60 C62 -21.5(3) . . . . ? C5 C6 C60 C62 157.0(2) . . . . ? O1 C6 C60 C63 -141.7(2) . . . . ? C5 C6 C60 C63 36.9(3) . . . . ? O1 C6 C60 C61 97.4(2) . . . . ? C5 C6 C60 C61 -84.1(3) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.159 _refine_diff_density_min -0.162 _refine_diff_density_rms 0.037 #===END data_7b_A(BCW410a) _database_code_CSD 175719 _audit_creation_method 'manual edited SHELXL-97 .cif file' _chemical_name_systematic ; R,S-2-(1-Isopropyl-4-(isopropylimino)-2-oxo-3-pivaloylazetidin -3-yl)-2,6-di-tert-butyl-5-methoxycarbonyl-1,3-dioxin-4(2H)-one ; _chemical_name_common ? _chemical_melting_point 394 _chemical_formula_moiety ? _chemical_formula_sum 'C28 H44 N2 O7' _chemical_formula_weight 520.65 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 16.964(5) _cell_length_b 11.267(3) _cell_length_c 17.010(5) _cell_angle_alpha 90.00 _cell_angle_beta 117.62(2) _cell_angle_gamma 90.00 _cell_volume 2880.7(14) _cell_formula_units_Z 4 _cell_measurement_temperature 90(2) _cell_measurement_reflns_used 71 _cell_measurement_theta_min 3.63 _cell_measurement_theta_max 18.93 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.36 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.200 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1128 _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 90(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Stoe 4-circle' _diffrn_measurement_method '\w' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 100 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 3.2 _diffrn_reflns_number 6210 _diffrn_reflns_av_R_equivalents 0.0308 _diffrn_reflns_av_sigmaI/netI 0.0742 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -1 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -1 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.70 _diffrn_reflns_theta_max 25.00 _reflns_number_total 5063 _reflns_number_gt 3621 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'local program' _computing_cell_refinement 'local program' _computing_data_reduction 'local program' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP (Johnson, 1965)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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. All equivalent bonds in the two parts of the disordered isopropylimino group are restrained to the same length (bonds to the atoms C41, C42, C43 compared to those to the atoms C46, C47, C48; instruction SAME of SHELXL97). The same was done for the disordered methoxy group (O52, C52 compared to O57, C57). The tert-butyl group disordered around the C6--C61 bond was refined without any constraints (except to fix the sum of the site occupation factors to 1). All the non-hydrogen atoms were refined with anisotropic displacement parameters. The H-atoms of the methyl groups were refined with common isotropic displacement parameters for the H-atoms of the same methyl group and idealized geometry with tetrahedral angles, staggered conformation, and C-H distances of 0.98 \%A (AFIX 33 of SHELXL97 for the methyl goups of the tert-butyl and isopropyl groups, AFIX 137 of SHELXL97 for the disordered methoxy goups), or of 1.00 \%A (AFIX 13 for the tertiary hydrogen atoms of the isopropyl groups). ; _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^)+(0.0264P)^2^+1.0561P] 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_number_reflns 5063 _refine_ls_number_parameters 433 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0939 _refine_ls_R_factor_gt 0.0601 _refine_ls_wR_factor_ref 0.1279 _refine_ls_wR_factor_gt 0.1118 _refine_ls_goodness_of_fit_ref 1.084 _refine_ls_restrained_S_all 1.083 _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 0.95786(10) 0.44116(14) 0.78707(11) 0.0205(4) Uani 1 1 d . . . C2 C 0.91454(15) 0.5530(2) 0.75802(15) 0.0176(5) Uani 1 1 d . . . O3 O 0.85977(10) 0.56016(15) 0.66375(10) 0.0205(4) Uani 1 1 d . . . C4 C 0.84891(16) 0.4687(2) 0.60721(17) 0.0235(6) Uani 1 1 d . . . O4 O 0.80247(13) 0.48645(18) 0.52917(12) 0.0388(5) Uani 1 1 d . . . C5 C 0.89282(15) 0.3582(2) 0.64507(16) 0.0195(5) Uani 1 1 d . A . C6 C 0.94657(15) 0.3489(2) 0.73289(16) 0.0197(6) Uani 1 1 d . A . C21 C 0.85236(15) 0.5685(2) 0.80105(16) 0.0185(5) Uani 1 1 d . . . C22 C 0.78241(16) 0.4700(2) 0.76644(18) 0.0272(6) Uani 1 1 d . . . H221 H 0.7487 0.4752 0.7017 0.037(5) Uiso 1 1 calc R . . H222 H 0.7418 0.4790 0.7923 0.037(5) Uiso 1 1 calc R . . H223 H 0.8119 0.3926 0.7831 0.037(5) Uiso 1 1 calc R . . C23 C 0.90392(16) 0.5579(2) 0.90215(16) 0.0231(6) Uani 1 1 d . . . H231 H 0.8629 0.5677 0.9275 0.040(5) Uiso 1 1 calc R . . H232 H 0.9498 0.6196 0.9255 0.040(5) Uiso 1 1 calc R . . H233 H 0.9321 0.4796 0.9181 0.040(5) Uiso 1 1 calc R . . C24 C 0.80499(16) 0.6885(2) 0.77689(17) 0.0226(6) Uani 1 1 d . . . H241 H 0.7716 0.6957 0.7122 0.030(4) Uiso 1 1 calc R . . H242 H 0.8491 0.7524 0.8005 0.030(4) Uiso 1 1 calc R . . H243 H 0.7640 0.6944 0.8025 0.030(4) Uiso 1 1 calc R . . C51 C 0.87688(16) 0.2634(2) 0.57827(17) 0.0228(6) Uani 1 1 d D . . O51 O 0.92413(13) 0.24298(17) 0.54573(13) 0.0359(5) Uani 1 1 d . A . O52 O 0.7932(3) 0.2211(6) 0.5455(6) 0.035(2) Uani 0.525(5) 1 d PD A 1 C52 C 0.7732(8) 0.1294(8) 0.4801(6) 0.038(2) Uani 0.525(5) 1 d PD A 1 H521 H 0.7734 0.1631 0.4271 0.050(12) Uiso 0.525(5) 1 calc PR A 1 H522 H 0.7144 0.0960 0.4643 0.050(12) Uiso 0.525(5) 1 calc PR A 1 H523 H 0.8182 0.0667 0.5044 0.050(12) Uiso 0.525(5) 1 calc PR A 1 O57 O 0.8113(4) 0.1879(6) 0.5689(6) 0.028(2) Uani 0.475(5) 1 d PD A 2 C57 C 0.7935(9) 0.0911(9) 0.5076(7) 0.039(3) Uani 0.475(5) 1 d PD A 2 H571 H 0.7784 0.1227 0.4486 0.055(14) Uiso 0.475(5) 1 calc PR A 2 H572 H 0.7435 0.0442 0.5046 0.055(14) Uiso 0.475(5) 1 calc PR A 2 H573 H 0.8464 0.0406 0.5279 0.055(14) Uiso 0.475(5) 1 calc PR A 2 C61 C 1.00017(16) 0.2431(2) 0.78601(18) 0.0256(6) Uani 1 1 d . . . C62 C 0.9501(4) 0.1313(4) 0.7478(4) 0.0318(15) Uani 0.525(5) 1 d P A 1 H621 H 0.9335 0.1273 0.6845 0.042(10) Uiso 0.525(5) 1 calc PR A 1 H622 H 0.8962 0.1300 0.7554 0.042(10) Uiso 0.525(5) 1 calc PR A 1 H623 H 0.9876 0.0630 0.7785 0.042(10) Uiso 0.525(5) 1 calc PR A 1 C63 C 1.0292(4) 0.2594(5) 0.8801(3) 0.0300(15) Uani 0.525(5) 1 d P A 1 H631 H 1.0634 0.1899 0.9128 0.021(7) Uiso 0.525(5) 1 calc PR A 1 H632 H 0.9771 0.2689 0.8901 0.021(7) Uiso 0.525(5) 1 calc PR A 1 H633 H 1.0666 0.3305 0.9009 0.021(7) Uiso 0.525(5) 1 calc PR A 1 C64 C 1.0854(3) 0.2460(5) 0.7687(4) 0.0296(14) Uani 0.525(5) 1 d P A 1 H641 H 1.0663 0.2353 0.7052 0.032(8) Uiso 0.525(5) 1 calc PR A 1 H642 H 1.1263 0.1819 0.8022 0.032(8) Uiso 0.525(5) 1 calc PR A 1 H643 H 1.1157 0.3226 0.7881 0.032(8) Uiso 0.525(5) 1 calc PR A 1 C67 C 1.0040(5) 0.1353(5) 0.7369(4) 0.0389(19) Uani 0.475(5) 1 d P A 2 H671 H 1.0406 0.0745 0.7793 0.038(11) Uiso 0.475(5) 1 calc PR A 2 H672 H 1.0302 0.1561 0.6981 0.038(11) Uiso 0.475(5) 1 calc PR A 2 H673 H 0.9437 0.1045 0.7010 0.038(11) Uiso 0.475(5) 1 calc PR A 2 C68 C 0.9553(4) 0.1985(5) 0.8482(4) 0.0351(18) Uani 0.475(5) 1 d P A 2 H681 H 0.9512 0.2656 0.8827 0.046(11) Uiso 0.475(5) 1 calc PR A 2 H682 H 0.9922 0.1361 0.8885 0.046(11) Uiso 0.475(5) 1 calc PR A 2 H683 H 0.8955 0.1672 0.8103 0.046(11) Uiso 0.475(5) 1 calc PR A 2 C69 C 1.0942(4) 0.2787(5) 0.8532(4) 0.0335(17) Uani 0.475(5) 1 d P A 2 H691 H 1.0918 0.3499 0.8851 0.054(12) Uiso 0.475(5) 1 calc PR A 2 H692 H 1.1294 0.2953 0.8222 0.054(12) Uiso 0.475(5) 1 calc PR A 2 H693 H 1.1219 0.2138 0.8955 0.054(12) Uiso 0.475(5) 1 calc PR A 2 N10 N 0.99698(13) 0.7244(2) 0.66840(14) 0.0275(5) Uani 1 1 d . . . C20 C 0.95363(16) 0.7583(2) 0.71576(16) 0.0212(6) Uani 1 1 d . . . O20 O 0.90784(11) 0.84351(16) 0.70707(11) 0.0271(4) Uani 1 1 d . . . C30 C 0.98881(15) 0.6474(2) 0.77776(16) 0.0192(5) Uani 1 1 d . . . C40 C 1.03604(16) 0.6229(3) 0.72085(17) 0.0268(6) Uani 1 1 d . B . C11 C 0.99667(18) 0.7810(3) 0.59011(18) 0.0347(7) Uani 1 1 d . . . H11 H 1.0261 0.7257 0.5658 0.024(7) Uiso 1 1 calc R . . C12 C 1.0487(2) 0.8946(3) 0.6155(2) 0.0394(8) Uani 1 1 d . . . H121 H 1.1102 0.8781 0.6598 0.037(5) Uiso 1 1 calc R . . H122 H 1.0216 0.9497 0.6406 0.037(5) Uiso 1 1 calc R . . H123 H 1.0484 0.9303 0.5629 0.037(5) Uiso 1 1 calc R . . C13 C 0.9013(2) 0.7991(4) 0.5195(2) 0.0677(13) Uani 1 1 d . . . H131 H 0.8703 0.7225 0.5045 0.070(7) Uiso 1 1 calc R . . H132 H 0.9008 0.8333 0.4663 0.070(7) Uiso 1 1 calc R . . H133 H 0.8711 0.8531 0.5419 0.070(7) Uiso 1 1 calc R . . C31 C 1.06009(16) 0.6583(2) 0.87607(16) 0.0214(6) Uani 1 1 d . . . O31 O 1.09160(11) 0.56671(16) 0.91473(11) 0.0264(4) Uani 1 1 d . . . C32 C 1.09704(18) 0.7778(2) 0.92030(17) 0.0296(6) Uani 1 1 d . . . C33 C 1.02486(19) 0.8582(2) 0.92180(19) 0.0376(7) Uani 1 1 d . . . H331 H 0.9787 0.8727 0.8609 0.047(5) Uiso 1 1 calc R . . H332 H 1.0514 0.9339 0.9500 0.047(5) Uiso 1 1 calc R . . H333 H 0.9983 0.8195 0.9554 0.047(5) Uiso 1 1 calc R . . C34 C 1.16782(18) 0.7543(3) 1.01559(18) 0.0355(7) Uani 1 1 d . . . H341 H 1.1928 0.8299 1.0451 0.052(6) Uiso 1 1 calc R . . H342 H 1.2153 0.7052 1.0151 0.052(6) Uiso 1 1 calc R . . H343 H 1.1408 0.7127 1.0477 0.052(6) Uiso 1 1 calc R . . C35 C 1.1407(2) 0.8396(3) 0.86971(19) 0.0447(9) Uani 1 1 d . . . H351 H 1.0958 0.8536 0.8082 0.060(6) Uiso 1 1 calc R . . H352 H 1.1879 0.7889 0.8704 0.060(6) Uiso 1 1 calc R . . H353 H 1.1661 0.9155 0.8983 0.060(6) Uiso 1 1 calc R . . N40 N 1.08982(15) 0.5436(2) 0.72688(15) 0.0372(6) Uani 1 1 d D . . C41 C 1.1223(4) 0.5164(7) 0.6600(4) 0.025(2) Uani 0.503(5) 1 d PD B 1 H41 H 1.0764 0.5428 0.6000 0.02(2) Uiso 0.503(5) 1 calc PR B 1 C42 C 1.1450(4) 0.3879(4) 0.6551(4) 0.0349(17) Uani 0.503(5) 1 d PD B 1 H421 H 1.0911 0.3394 0.6351 0.043(10) Uiso 0.503(5) 1 calc PR B 1 H422 H 1.1893 0.3611 0.7139 0.043(10) Uiso 0.503(5) 1 calc PR B 1 H423 H 1.1692 0.3798 0.6131 0.043(10) Uiso 0.503(5) 1 calc PR B 1 C43 C 1.2037(4) 0.5949(5) 0.6900(4) 0.0341(17) Uani 0.503(5) 1 d PD B 1 H431 H 1.1868 0.6778 0.6913 0.032(10) Uiso 0.503(5) 1 calc PR B 1 H432 H 1.2287 0.5867 0.6486 0.032(10) Uiso 0.503(5) 1 calc PR B 1 H433 H 1.2483 0.5709 0.7496 0.032(10) Uiso 0.503(5) 1 calc PR B 1 C46 C 1.1349(5) 0.5665(6) 0.6701(5) 0.030(2) Uani 0.497(5) 1 d PD B 2 H46 H 1.1372 0.6530 0.6583 0.018(13) Uiso 0.497(5) 1 calc PR B 2 C47 C 1.0765(4) 0.4988(7) 0.5868(4) 0.0396(19) Uani 0.497(5) 1 d PD B 2 H471 H 1.0182 0.5376 0.5564 0.042(10) Uiso 0.497(5) 1 calc PR B 2 H472 H 1.0688 0.4173 0.6022 0.042(10) Uiso 0.497(5) 1 calc PR B 2 H473 H 1.1043 0.4975 0.5476 0.042(10) Uiso 0.497(5) 1 calc PR B 2 C48 C 1.2269(4) 0.5126(7) 0.7191(5) 0.055(2) Uani 0.497(5) 1 d PD B 2 H481 H 1.2633 0.5605 0.7716 0.046(11) Uiso 0.497(5) 1 calc PR B 2 H482 H 1.2548 0.5107 0.6799 0.046(11) Uiso 0.497(5) 1 calc PR B 2 H483 H 1.2222 0.4315 0.7374 0.046(11) Uiso 0.497(5) 1 calc PR B 2 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 0.0234(9) 0.0157(9) 0.0215(9) -0.0029(8) 0.0095(8) 0.0063(7) C2 0.0179(12) 0.0177(12) 0.0176(12) 0.0000(11) 0.0087(10) 0.0031(10) O3 0.0217(9) 0.0205(9) 0.0174(8) -0.0015(8) 0.0076(7) 0.0045(8) C4 0.0210(13) 0.0276(15) 0.0238(14) -0.0071(12) 0.0119(12) 0.0019(11) O4 0.0434(12) 0.0422(12) 0.0199(10) -0.0045(10) 0.0054(9) 0.0194(10) C5 0.0184(12) 0.0208(13) 0.0232(13) -0.0039(11) 0.0130(11) -0.0007(11) C6 0.0190(12) 0.0175(13) 0.0286(14) -0.0040(12) 0.0161(11) 0.0001(10) C21 0.0196(12) 0.0156(12) 0.0240(13) 0.0015(11) 0.0132(11) 0.0008(11) C22 0.0211(13) 0.0240(15) 0.0382(16) 0.0037(13) 0.0152(12) -0.0019(11) C23 0.0259(13) 0.0246(14) 0.0241(13) 0.0039(12) 0.0161(11) 0.0044(12) C24 0.0249(13) 0.0216(14) 0.0265(14) 0.0010(12) 0.0164(12) 0.0052(11) C51 0.0276(14) 0.0196(14) 0.0231(13) -0.0017(12) 0.0134(12) -0.0008(12) O51 0.0463(12) 0.0327(11) 0.0470(12) -0.0139(10) 0.0371(11) -0.0091(10) O52 0.026(3) 0.035(4) 0.042(4) -0.014(3) 0.013(3) -0.002(3) C52 0.033(5) 0.029(5) 0.047(6) -0.017(4) 0.014(4) -0.003(4) O57 0.019(3) 0.026(4) 0.042(5) -0.021(3) 0.016(3) -0.009(3) C57 0.032(6) 0.029(6) 0.052(7) -0.025(5) 0.016(5) -0.007(4) C61 0.0244(13) 0.0178(13) 0.0352(15) -0.0028(12) 0.0144(12) 0.0046(11) C62 0.036(3) 0.016(3) 0.048(4) 0.011(3) 0.022(3) 0.007(2) C63 0.044(3) 0.023(3) 0.033(3) 0.015(2) 0.027(3) 0.017(3) C64 0.025(3) 0.029(3) 0.037(3) 0.007(3) 0.016(2) 0.012(2) C67 0.057(5) 0.023(3) 0.035(4) 0.000(3) 0.019(3) 0.015(3) C68 0.040(4) 0.030(4) 0.044(4) 0.020(3) 0.027(3) 0.013(3) C69 0.030(3) 0.023(3) 0.040(4) 0.005(3) 0.010(3) 0.005(3) N10 0.0216(11) 0.0416(14) 0.0237(11) 0.0124(11) 0.0141(10) 0.0013(11) C20 0.0198(12) 0.0245(14) 0.0189(13) 0.0029(11) 0.0086(11) -0.0042(12) O20 0.0291(10) 0.0207(10) 0.0289(10) 0.0049(9) 0.0113(9) -0.0018(8) C30 0.0196(12) 0.0212(13) 0.0195(13) 0.0024(11) 0.0113(11) -0.0009(11) C40 0.0185(13) 0.0426(17) 0.0201(13) 0.0071(13) 0.0098(11) 0.0000(13) C11 0.0310(15) 0.0501(19) 0.0290(15) 0.0164(15) 0.0190(13) 0.0004(14) C12 0.0538(19) 0.0369(17) 0.0444(18) 0.0175(15) 0.0370(16) 0.0075(15) C13 0.0346(17) 0.130(4) 0.0347(18) 0.042(2) 0.0131(16) 0.000(2) C31 0.0194(13) 0.0258(14) 0.0238(14) 0.0025(12) 0.0142(11) -0.0030(11) O31 0.0237(9) 0.0272(10) 0.0260(10) 0.0054(9) 0.0096(8) 0.0017(8) C32 0.0313(14) 0.0283(15) 0.0227(14) 0.0043(13) 0.0071(12) -0.0114(13) C33 0.0491(18) 0.0218(15) 0.0302(16) -0.0025(13) 0.0085(14) -0.0055(14) C34 0.0338(15) 0.0375(17) 0.0257(15) 0.0009(14) 0.0058(13) -0.0155(14) C35 0.0420(18) 0.050(2) 0.0284(16) 0.0087(16) 0.0049(14) -0.0269(16) N40 0.0250(12) 0.0646(18) 0.0307(13) 0.0136(13) 0.0203(11) 0.0170(13) C41 0.020(3) 0.031(5) 0.032(4) 0.002(4) 0.018(3) -0.002(3) C42 0.040(4) 0.030(3) 0.054(4) -0.003(3) 0.038(3) 0.005(3) C43 0.033(4) 0.037(4) 0.042(4) -0.005(3) 0.026(3) -0.005(3) C46 0.034(5) 0.028(5) 0.044(4) 0.003(4) 0.032(4) 0.002(4) C47 0.074(5) 0.030(4) 0.041(4) -0.002(3) 0.048(4) 0.002(3) C48 0.050(4) 0.056(5) 0.089(6) 0.031(5) 0.057(4) 0.029(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C6 1.343(3) . yes O1 C2 1.426(3) . yes C2 O3 1.435(3) . yes C2 C21 1.548(3) . ? C2 C30 1.562(3) . yes O3 C4 1.362(3) . yes C4 O4 1.205(3) . yes C4 C5 1.441(3) . yes C5 C6 1.346(3) . yes C5 C51 1.490(3) . ? C6 C61 1.517(3) . ? C21 C24 1.529(3) . ? C21 C22 1.529(3) . ? C21 C23 1.530(3) . ? C22 H221 0.9800 . ? C22 H222 0.9800 . ? C22 H223 0.9800 . ? C23 H231 0.9800 . ? C23 H232 0.9800 . ? C23 H233 0.9800 . ? C24 H241 0.9800 . ? C24 H242 0.9800 . ? C24 H243 0.9800 . ? C51 O51 1.189(3) . ? C51 O52 1.349(4) . ? C51 O57 1.350(4) . ? O52 C52 1.439(5) . ? C52 H521 0.9800 . ? C52 H522 0.9800 . ? C52 H523 0.9800 . ? O57 C57 1.440(5) . ? C57 H571 0.9800 . ? C57 H572 0.9800 . ? C57 H573 0.9800 . ? C61 C63 1.451(6) . ? C61 C62 1.489(6) . ? C61 C67 1.493(6) . ? C61 C69 1.524(6) . ? C61 C64 1.604(5) . ? C61 C68 1.642(6) . ? C62 H621 0.9800 . ? C62 H622 0.9800 . ? C62 H623 0.9800 . ? C63 H631 0.9800 . ? C63 H632 0.9800 . ? C63 H633 0.9800 . ? C64 H641 0.9800 . ? C64 H642 0.9800 . ? C64 H643 0.9800 . ? C67 H671 0.9800 . ? C67 H672 0.9800 . ? C67 H673 0.9800 . ? C68 H681 0.9800 . ? C68 H682 0.9800 . ? C68 H683 0.9800 . ? C69 H691 0.9800 . ? C69 H692 0.9800 . ? C69 H693 0.9800 . ? N10 C20 1.373(3) . yes N10 C40 1.412(3) . yes N10 C11 1.474(3) . yes C20 O20 1.200(3) . yes C20 C30 1.564(3) . yes C30 C31 1.549(3) . yes C30 C40 1.541(3) . yes C40 N40 1.247(3) . yes C11 C12 1.501(4) . ? C11 C13 1.517(4) . ? C11 H11 1.0000 . ? C12 H121 0.9800 . ? C12 H122 0.9800 . ? C12 H123 0.9800 . ? C13 H131 0.9800 . ? C13 H132 0.9800 . ? C13 H133 0.9800 . ? C31 O31 1.207(3) . yes C31 C32 1.528(4) . ? C32 C34 1.528(4) . ? C32 C33 1.533(4) . ? C32 C35 1.538(4) . ? C33 H331 0.9800 . ? C33 H332 0.9800 . ? C33 H333 0.9800 . ? C34 H341 0.9800 . ? C34 H342 0.9800 . ? C34 H343 0.9800 . ? C35 H351 0.9800 . ? C35 H352 0.9800 . ? C35 H353 0.9800 . ? N40 C46 1.506(5) . ? N40 C41 1.507(5) . yes C41 C42 1.511(9) . ? C41 C43 1.516(6) . ? C41 H41 1.0000 . ? C42 H421 0.9800 . ? C42 H422 0.9800 . ? C42 H423 0.9800 . ? C43 H431 0.9800 . ? C43 H432 0.9800 . ? C43 H433 0.9800 . ? C46 C47 1.506(9) . ? C46 C48 1.515(6) . ? C46 H46 1.0000 . ? C47 H471 0.9800 . ? C47 H472 0.9800 . ? C47 H473 0.9800 . ? C48 H481 0.9800 . ? C48 H482 0.9800 . ? C48 H483 0.9800 . ? 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 O1 C2 124.01(18) . . yes O1 C2 O3 113.56(19) . . yes O1 C2 C21 106.90(19) . . ? O3 C2 C21 106.98(18) . . ? O1 C2 C30 107.01(18) . . yes O3 C2 C30 103.97(18) . . yes C21 C2 C30 118.7(2) . . ? C4 O3 C2 123.49(19) . . yes O4 C4 O3 117.2(2) . . yes O4 C4 C5 125.0(2) . . yes O3 C4 C5 117.7(2) . . yes C6 C5 C4 120.5(2) . . yes C4 C5 C51 113.9(2) . . yes C6 C5 C51 125.5(2) . . yes O1 C6 C5 120.6(2) . . yes O1 C6 C61 110.1(2) . . yes C5 C6 C61 129.2(2) . . yes C24 C21 C22 108.74(19) . . ? C24 C21 C23 109.1(2) . . ? C22 C21 C23 108.3(2) . . ? C24 C21 C2 111.2(2) . . ? C22 C21 C2 108.3(2) . . ? C23 C21 C2 111.28(19) . . ? C21 C22 H221 109.5 . . ? C21 C22 H222 109.5 . . ? H221 C22 H222 109.5 . . ? C21 C22 H223 109.5 . . ? H221 C22 H223 109.5 . . ? H222 C22 H223 109.5 . . ? C21 C23 H231 109.5 . . ? C21 C23 H232 109.5 . . ? H231 C23 H232 109.5 . . ? C21 C23 H233 109.5 . . ? H231 C23 H233 109.5 . . ? H232 C23 H233 109.5 . . ? C21 C24 H241 109.5 . . ? C21 C24 H242 109.5 . . ? H241 C24 H242 109.5 . . ? C21 C24 H243 109.5 . . ? H241 C24 H243 109.5 . . ? H242 C24 H243 109.5 . . ? O51 C51 O52 123.1(5) . . ? O51 C51 O57 121.3(5) . . ? O52 C51 O57 22.6(5) . . ? O51 C51 C5 124.8(2) . . ? O52 C51 C5 110.6(4) . . ? O57 C51 C5 113.0(4) . . ? C51 O52 C52 113.5(8) . . ? C51 O57 C57 116.7(9) . . ? O57 C57 H571 109.5 . . ? O57 C57 H572 109.5 . . ? H571 C57 H572 109.5 . . ? O57 C57 H573 109.5 . . ? H571 C57 H573 109.5 . . ? H572 C57 H573 109.5 . . ? C63 C61 C62 114.9(4) . . ? C63 C61 C67 129.8(4) . . ? C62 C61 C67 39.8(3) . . ? C63 C61 C6 111.1(3) . . ? C62 C61 C6 110.0(3) . . ? C67 C61 C6 118.4(3) . . ? C63 C61 C69 55.8(3) . . ? C62 C61 C69 137.5(4) . . ? C67 C61 C69 109.4(4) . . ? C6 C61 C69 111.7(3) . . ? C63 C61 C64 109.0(3) . . ? C62 C61 C64 108.5(3) . . ? C67 C61 C64 68.7(4) . . ? C6 C61 C64 102.5(3) . . ? C69 C61 C64 54.1(3) . . ? C63 C61 C68 49.5(3) . . ? C62 C61 C68 71.4(3) . . ? C67 C61 C68 105.4(4) . . ? C6 C61 C68 107.2(3) . . ? C69 C61 C68 103.6(4) . . ? C64 C61 C68 148.3(3) . . ? C61 C62 H621 109.5 . . ? C61 C62 H622 109.5 . . ? H621 C62 H622 109.5 . . ? C61 C62 H623 109.5 . . ? H621 C62 H623 109.5 . . ? H622 C62 H623 109.5 . . ? C61 C63 H631 109.5 . . ? C61 C63 H632 109.5 . . ? H631 C63 H632 109.5 . . ? C61 C63 H633 109.5 . . ? H631 C63 H633 109.5 . . ? H632 C63 H633 109.5 . . ? C61 C64 H641 109.5 . . ? C61 C64 H642 109.5 . . ? H641 C64 H642 109.5 . . ? C61 C64 H643 109.5 . . ? H641 C64 H643 109.5 . . ? H642 C64 H643 109.5 . . ? C61 C67 H671 109.5 . . ? C61 C67 H672 109.5 . . ? H671 C67 H672 109.5 . . ? C61 C67 H673 109.5 . . ? H671 C67 H673 109.5 . . ? H672 C67 H673 109.5 . . ? C61 C68 H681 109.5 . . ? C61 C68 H682 109.5 . . ? H681 C68 H682 109.5 . . ? C61 C68 H683 109.5 . . ? H681 C68 H683 109.5 . . ? H682 C68 H683 109.5 . . ? C61 C69 H691 109.5 . . ? C61 C69 H692 109.5 . . ? H691 C69 H692 109.5 . . ? C61 C69 H693 109.5 . . ? H691 C69 H693 109.5 . . ? H692 C69 H693 109.5 . . ? C20 N10 C40 94.4(2) . . yes C20 N10 C11 129.1(2) . . yes C40 N10 C11 136.5(2) . . yes O20 C20 N10 130.0(2) . . yes O20 C20 C30 138.2(2) . . yes N10 C20 C30 91.9(2) . . yes C40 C30 C31 108.62(19) . . ? C40 C30 C2 110.2(2) . . ? C31 C30 C2 115.7(2) . . ? C20 C30 C40 82.34(18) . . yes C31 C30 C20 121.9(2) . . ? C2 C30 C20 112.44(19) . . ? N40 C40 N10 138.0(2) . . yes N40 C40 C30 130.6(2) . . yes N10 C40 C30 91.3(2) . . yes N10 C11 C12 110.7(2) . . ? N10 C11 C13 109.2(2) . . ? C12 C11 C13 112.5(3) . . ? N10 C11 H11 108.1 . . ? C12 C11 H11 108.1 . . ? C13 C11 H11 108.1 . . ? C11 C12 H121 109.5 . . ? C11 C12 H122 109.5 . . ? H121 C12 H122 109.5 . . ? C11 C12 H123 109.5 . . ? H121 C12 H123 109.5 . . ? H122 C12 H123 109.5 . . ? C11 C13 H131 109.5 . . ? C11 C13 H132 109.5 . . ? H131 C13 H132 109.5 . . ? C11 C13 H133 109.5 . . ? H131 C13 H133 109.5 . . ? H132 C13 H133 109.5 . . ? O31 C31 C32 120.5(2) . . ? O31 C31 C30 116.6(2) . . ? C32 C31 C30 122.6(2) . . ? C31 C32 C34 108.1(2) . . ? C31 C32 C33 112.4(2) . . ? C34 C32 C33 109.0(2) . . ? C31 C32 C35 108.5(2) . . ? C34 C32 C35 109.1(2) . . ? C33 C32 C35 109.7(2) . . ? C32 C33 H331 109.5 . . ? C32 C33 H332 109.5 . . ? H331 C33 H332 109.5 . . ? C32 C33 H333 109.5 . . ? H331 C33 H333 109.5 . . ? H332 C33 H333 109.5 . . ? C32 C34 H341 109.5 . . ? C32 C34 H342 109.5 . . ? H341 C34 H342 109.5 . . ? C32 C34 H343 109.5 . . ? H341 C34 H343 109.5 . . ? H342 C34 H343 109.5 . . ? C32 C35 H351 109.5 . . ? C32 C35 H352 109.5 . . ? H351 C35 H352 109.5 . . ? C32 C35 H353 109.5 . . ? H351 C35 H353 109.5 . . ? H352 C35 H353 109.5 . . ? C40 N40 C46 113.2(3) . . ? C40 N40 C41 126.4(4) . . yes C46 N40 C41 23.0(3) . . ? N40 C41 C42 115.4(6) . . ? N40 C41 C43 102.8(4) . . ? C42 C41 C43 111.2(5) . . ? N40 C41 H41 109.0 . . ? C42 C41 H41 109.0 . . ? C43 C41 H41 109.0 . . ? C41 C42 H421 109.5 . . ? C41 C42 H422 109.5 . . ? H421 C42 H422 109.5 . . ? C41 C42 H423 109.5 . . ? H421 C42 H423 109.5 . . ? H422 C42 H423 109.5 . . ? C41 C43 H431 109.5 . . ? C41 C43 H432 109.5 . . ? H431 C43 H432 109.5 . . ? C41 C43 H433 109.5 . . ? H431 C43 H433 109.5 . . ? H432 C43 H433 109.5 . . ? N40 C46 C47 102.0(5) . . ? N40 C46 C48 106.2(5) . . ? C47 C46 C48 112.0(5) . . ? N40 C46 H46 112.0 . . ? C47 C46 H46 112.0 . . ? C48 C46 H46 112.0 . . ? C46 C47 H471 109.5 . . ? C46 C47 H472 109.5 . . ? H471 C47 H472 109.5 . . ? C46 C47 H473 109.5 . . ? H471 C47 H473 109.5 . . ? H472 C47 H473 109.5 . . ? C46 C48 H481 109.5 . . ? C46 C48 H482 109.5 . . ? H481 C48 H482 109.5 . . ? C46 C48 H483 109.5 . . ? H481 C48 H483 109.5 . . ? H482 C48 H483 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 O1 C2 O3 -2.5(3) . . . . yes O1 C2 O3 C4 0.9(3) . . . . yes C2 O3 C4 C5 2.0(3) . . . . yes O3 C4 C5 C6 -3.7(3) . . . . yes C4 C5 C6 O1 2.2(4) . . . . yes C5 C6 O1 C2 1.0(3) . . . . yes C6 O1 C2 C21 115.2(2) . . . . ? C6 O1 C2 C30 -116.6(2) . . . . ? C21 C2 O3 C4 -116.8(2) . . . . ? C30 C2 O3 C4 116.8(2) . . . . ? C2 O3 C4 O4 -178.6(2) . . . . yes O4 C4 C5 C6 177.0(3) . . . . ? O4 C4 C5 C51 0.5(4) . . . . ? O3 C4 C5 C51 179.8(2) . . . . yes C2 O1 C6 C61 -178.20(19) . . . . ? C51 C5 C6 O1 178.3(2) . . . . ? C4 C5 C6 C61 -178.7(2) . . . . ? C51 C5 C6 C61 -2.7(4) . . . . ? O1 C2 C21 C24 177.83(18) . . . . ? O3 C2 C21 C24 -60.2(2) . . . . ? C30 C2 C21 C24 56.8(3) . . . . ? O1 C2 C21 C22 -62.8(2) . . . . ? O3 C2 C21 C22 59.2(2) . . . . ? C30 C2 C21 C22 176.2(2) . . . . ? O1 C2 C21 C23 56.1(2) . . . . ? O3 C2 C21 C23 178.0(2) . . . . ? C30 C2 C21 C23 -64.9(3) . . . . ? C6 C5 C51 O51 -82.6(4) . . . . ? C4 C5 C51 O51 93.7(3) . . . . yes C6 C5 C51 O52 110.6(4) . . . . ? C4 C5 C51 O52 -73.1(4) . . . . ? C6 C5 C51 O57 86.4(5) . . . . ? C4 C5 C51 O57 -97.3(4) . . . . ? O51 C51 O52 C52 12.7(8) . . . . ? O57 C51 O52 C52 -80(2) . . . . ? C5 C51 O52 C52 179.7(5) . . . . ? O51 C51 O57 C57 -8.6(9) . . . . ? O52 C51 O57 C57 93(2) . . . . ? C5 C51 O57 C57 -178.0(6) . . . . ? O1 C6 C61 C63 14.9(4) . . . . ? C5 C6 C61 C63 -164.2(3) . . . . ? O1 C6 C61 C62 143.3(3) . . . . ? C5 C6 C61 C62 -35.8(4) . . . . ? O1 C6 C61 C67 -173.8(4) . . . . ? C5 C6 C61 C67 7.1(5) . . . . ? O1 C6 C61 C69 -45.4(4) . . . . ? C5 C6 C61 C69 135.5(4) . . . . ? O1 C6 C61 C64 -101.4(3) . . . . ? C5 C6 C61 C64 79.5(4) . . . . ? O1 C6 C61 C68 67.4(3) . . . . ? C5 C6 C61 C68 -111.7(4) . . . . ? C40 N10 C20 O20 177.9(3) . . . . ? C11 N10 C20 O20 -2.9(5) . . . . yes C40 N10 C20 C30 -1.9(2) . . . . ? C11 N10 C20 C30 177.4(3) . . . . ? O1 C2 C30 C40 65.2(2) . . . . ? O3 C2 C30 C40 -55.2(2) . . . . ? C21 C2 C30 C40 -173.9(2) . . . . yes O1 C2 C30 C31 -58.5(3) . . . . yes O3 C2 C30 C31 -178.94(19) . . . . yes C21 C2 C30 C31 62.4(3) . . . . ? O1 C2 C30 C20 155.11(18) . . . . yes O3 C2 C30 C20 34.7(2) . . . . yes C21 C2 C30 C20 -84.0(3) . . . . ? O20 C20 C30 C40 -178.0(3) . . . . yes N10 C20 C30 C40 1.76(18) . . . . yes O20 C20 C30 C31 -70.8(4) . . . . ? N10 C20 C30 C31 109.0(2) . . . . ? O20 C20 C30 C2 73.3(4) . . . . ? N10 C20 C30 C2 -107.0(2) . . . . ? C20 N10 C40 N40 -175.3(4) . . . . ? C11 N10 C40 N40 5.5(6) . . . . yes C20 N10 C40 C30 1.9(2) . . . . ? C11 N10 C40 C30 -177.3(3) . . . . ? C31 C30 C40 N40 54.8(4) . . . . ? C2 C30 C40 N40 -73.0(4) . . . . ? C20 C30 C40 N40 175.9(3) . . . . ? C31 C30 C40 N10 -122.8(2) . . . . ? C2 C30 C40 N10 109.4(2) . . . . ? C20 C30 C40 N10 -1.71(18) . . . . ? C20 N10 C11 C12 71.9(3) . . . . ? C40 N10 C11 C12 -109.2(3) . . . . ? C20 N10 C11 C13 -52.5(4) . . . . ? C40 N10 C11 C13 126.4(3) . . . . ? C40 C30 C31 O31 -77.6(3) . . . . ? C2 C30 C31 O31 46.9(3) . . . . ? C20 C30 C31 O31 -170.1(2) . . . . ? C40 C30 C31 C32 95.9(3) . . . . ? C2 C30 C31 C32 -139.6(2) . . . . ? C20 C30 C31 C32 3.3(3) . . . . ? O31 C31 C32 C34 -4.8(3) . . . . ? C30 C31 C32 C34 -178.0(2) . . . . ? O31 C31 C32 C33 -125.1(3) . . . . ? C30 C31 C32 C33 61.7(3) . . . . ? O31 C31 C32 C35 113.4(3) . . . . ? C30 C31 C32 C35 -59.8(3) . . . . ? N10 C40 N40 C46 8.6(6) . . . . ? C30 C40 N40 C46 -167.8(4) . . . . ? N10 C40 N40 C41 -13.2(6) . . . . yes C30 C40 N40 C41 170.5(4) . . . . ? C40 N40 C41 C42 -149.0(4) . . . . ? C46 N40 C41 C42 149.9(15) . . . . ? C40 N40 C41 C43 89.7(6) . . . . ? C46 N40 C41 C43 28.7(9) . . . . ? C40 N40 C46 C47 -94.2(5) . . . . ? C41 N40 C46 C47 35.8(12) . . . . ? C40 N40 C46 C48 148.3(5) . . . . ? C41 N40 C46 C48 -81.7(11) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.209 _refine_diff_density_min -0.246 _refine_diff_density_rms 0.046 #===END data_7b_B(BCW410c) _database_code_CSD 175720 _audit_creation_method 'manual edited SHELXL-97 .cif file' _chemical_name_systematic ; R,R-2-(1-Isopropyl-4-(isopropylimino)-2-oxo-3-pivaloylazetidin -3-yl)-2,6-di-tert-butyl-5-methoxycarbonyl-1,3-dioxin-4(2H)-one ; _chemical_name_common ? _chemical_melting_point 394 _chemical_formula_moiety ? _chemical_formula_sum 'C28 H44 N2 O7' _chemical_formula_weight 520.65 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 'P 21 21 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 9.885(3) _cell_length_b 16.338(5) _cell_length_c 17.537(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2832.2(15) _cell_formula_units_Z 4 _cell_measurement_temperature 90(2) _cell_measurement_reflns_used 68 _cell_measurement_theta_min 3.71 _cell_measurement_theta_max 18.78 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.221 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1128 _exptl_absorpt_coefficient_mu 0.087 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 90(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Stoe 4-circle' _diffrn_measurement_method '\w-2\q' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 100 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 3.9 _diffrn_reflns_number 3991 _diffrn_reflns_av_R_equivalents 0.0233 _diffrn_reflns_av_sigmaI/netI 0.0535 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.67 _diffrn_reflns_theta_max 24.94 _reflns_number_total 3660 _reflns_number_gt 3296 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'local program' _computing_cell_refinement 'local program' _computing_data_reduction 'local program' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP (Johnson, 1965)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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. All equivalent bonds in the two parts of the disordered group (consisting of the methoxycarbonyl group and the atoms O3, C4, O4 and C5 of the 1,3-dioxin-4(2H)-one ring) are restrained to the same length by the instruction SAME of SHELXL97 [equivalent atoms: O3, C4, O4, C5, C51, O51, O52, C52 with site occupation factor of 0.714(4) and O35, C45, O45, C55, C56, O56, O57, C57 with site occupation factor of 0.286(4)]. The non- hydrogen atoms of the less occupied disordered fragment were refined with isotropic displacement parameters, all the other non-hydrogen atoms were refined with anisotropic displacement parameters. The H-atoms of the methyl groups were refined with common isotropic displacement parameters for the H-atoms of the same methyl group and idealized geometry with tetrahedral angles, staggered conformation, and C-H distances of 0.98 \%A (AFIX 33 of SHELXL97 for the methyl goups of the tert-butyl and isopropyl groups, AFIX 137 of SHELXL97 for the disordered methoxy groups), or of 1.00 \%A (AFIX 13 for the tertiary hydrogen atoms of the isopropyl groups). Due to the absence of heavier atoms the absolute structure cannot be determined reliably. (The Flack parameter x for the inverted absolute structure resulted in 3.4(12) instead of -2.4(12).) ; _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^)+(0.0223P)^2^+1.0042P] 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 -2.5(12) _refine_ls_number_reflns 3660 _refine_ls_number_parameters 386 _refine_ls_number_restraints 16 _refine_ls_R_factor_all 0.0477 _refine_ls_R_factor_gt 0.0400 _refine_ls_wR_factor_ref 0.0915 _refine_ls_wR_factor_gt 0.0861 _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_restrained_S_all 1.041 _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 0.53574(17) 0.97181(10) 0.43399(10) 0.0214(4) Uani 1 1 d . A . C2 C 0.4771(2) 0.94797(15) 0.36203(14) 0.0190(5) Uani 1 1 d D . . O3 O 0.4524(16) 1.0140(3) 0.3110(5) 0.023(3) Uani 0.714(4) 1 d PD A 1 C4 C 0.5164(6) 1.0880(3) 0.3192(3) 0.0182(13) Uani 0.714(4) 1 d PD A 1 O4 O 0.5043(4) 1.13629(19) 0.26786(18) 0.0248(8) Uani 0.714(4) 1 d PD A 1 C5 C 0.5881(4) 1.1025(2) 0.3898(2) 0.0208(10) Uani 0.714(4) 1 d PD A 1 C51 C 0.6579(4) 1.1842(2) 0.3923(2) 0.0224(9) Uani 0.714(4) 1 d PD A 1 O51 O 0.7629(3) 1.19841(16) 0.36109(16) 0.0335(8) Uani 0.714(4) 1 d PD A 1 O52 O 0.5843(3) 1.23991(15) 0.42992(15) 0.0270(7) Uani 0.714(4) 1 d PD A 1 C52 C 0.6456(6) 1.3205(2) 0.4317(4) 0.0328(13) Uani 0.714(4) 1 d PD A 1 H521 H 0.7332 1.3174 0.4578 0.042(8) Uiso 0.714(4) 1 calc PR A 1 H522 H 0.5862 1.3584 0.4592 0.042(8) Uiso 0.714(4) 1 calc PR A 1 H523 H 0.6591 1.3401 0.3795 0.042(8) Uiso 0.714(4) 1 calc PR A 1 O35 O 0.461(3) 1.0180(5) 0.3141(9) 0.008(6) Uiso 0.286(4) 1 d PD A 2 C45 C 0.4916(17) 1.0977(4) 0.3326(5) 0.023(6) Uiso 0.286(4) 1 d PD A 2 O45 O 0.4687(10) 1.1491(4) 0.2852(4) 0.029(3) Uiso 0.286(4) 1 d PD A 2 C55 C 0.5500(9) 1.1114(3) 0.4070(4) 0.018(4) Uiso 0.286(4) 1 d PD A 2 C56 C 0.5620(7) 1.2000(4) 0.4286(4) 0.017(2) Uiso 0.286(4) 1 d PD A 2 O56 O 0.4928(6) 1.2327(3) 0.4755(3) 0.0248(18) Uiso 0.286(4) 1 d PD A 2 O57 O 0.6633(6) 1.2366(4) 0.3912(3) 0.0253(19) Uiso 0.286(4) 1 d PD A 2 C57 C 0.6885(14) 1.3201(5) 0.4151(10) 0.035(5) Uiso 0.286(4) 1 d PD A 2 H571 H 0.6021 1.3478 0.4242 0.022(16) Uiso 0.286(4) 1 calc PR A 2 H572 H 0.7384 1.3490 0.3750 0.022(16) Uiso 0.286(4) 1 calc PR A 2 H573 H 0.7419 1.3199 0.4621 0.022(16) Uiso 0.286(4) 1 calc PR A 2 C6 C 0.5876(2) 1.04676(15) 0.44742(15) 0.0213(6) Uani 1 1 d . . . C21 C 0.5796(3) 0.88849(17) 0.32278(17) 0.0276(6) Uani 1 1 d . A . C22 C 0.7128(3) 0.9349(2) 0.3099(2) 0.0395(8) Uani 1 1 d . . . H221 H 0.7482 0.9539 0.3590 0.044(5) Uiso 1 1 calc R A . H222 H 0.6963 0.9821 0.2767 0.044(5) Uiso 1 1 calc R . . H223 H 0.7788 0.8984 0.2858 0.044(5) Uiso 1 1 calc R . . C23 C 0.6080(3) 0.81411(18) 0.3723(2) 0.0405(8) Uani 1 1 d . . . H231 H 0.5237 0.7840 0.3809 0.043(5) Uiso 1 1 calc R A . H232 H 0.6454 0.8319 0.4213 0.043(5) Uiso 1 1 calc R . . H233 H 0.6733 0.7785 0.3465 0.043(5) Uiso 1 1 calc R . . C24 C 0.5285(3) 0.86021(18) 0.24451(18) 0.0350(7) Uani 1 1 d . . . H241 H 0.4437 0.8299 0.2508 0.042(5) Uiso 1 1 calc R A . H242 H 0.5964 0.8246 0.2208 0.042(5) Uiso 1 1 calc R . . H243 H 0.5129 0.9080 0.2119 0.042(5) Uiso 1 1 calc R . . C61 C 0.6469(3) 1.05232(16) 0.52757(15) 0.0255(6) Uani 1 1 d . A . C62 C 0.7735(3) 1.10623(18) 0.52915(16) 0.0309(7) Uani 1 1 d . . . H621 H 0.8408 1.0843 0.4936 0.039(5) Uiso 1 1 calc R A . H622 H 0.8113 1.1067 0.5808 0.039(5) Uiso 1 1 calc R . . H623 H 0.7495 1.1621 0.5141 0.039(5) Uiso 1 1 calc R . . C63 C 0.6856(3) 0.96714(17) 0.55559(17) 0.0337(7) Uani 1 1 d . . . H631 H 0.7542 0.9438 0.5216 0.042(5) Uiso 1 1 calc R A . H632 H 0.6054 0.9319 0.5558 0.042(5) Uiso 1 1 calc R . . H633 H 0.7223 0.9710 0.6074 0.042(5) Uiso 1 1 calc R . . C64 C 0.5388(3) 1.0887(2) 0.57968(18) 0.0424(8) Uani 1 1 d . . . H641 H 0.5740 1.0924 0.6318 0.046(5) Uiso 1 1 calc R A . H642 H 0.4584 1.0536 0.5791 0.046(5) Uiso 1 1 calc R . . H643 H 0.5145 1.1435 0.5616 0.046(5) Uiso 1 1 calc R . . N10 N 0.2688(2) 0.93527(12) 0.49995(11) 0.0181(5) Uani 1 1 d . A . C20 C 0.3367(3) 0.87184(15) 0.46624(14) 0.0193(6) Uani 1 1 d . . . O20 O 0.37819(19) 0.80825(11) 0.49087(11) 0.0278(5) Uani 1 1 d . A . C30 C 0.3347(2) 0.91517(14) 0.38624(14) 0.0162(5) Uani 1 1 d . A . C40 C 0.2512(2) 0.98084(15) 0.43252(14) 0.0165(5) Uani 1 1 d . . . C11 C 0.2147(3) 0.95108(17) 0.57656(14) 0.0248(6) Uani 1 1 d . . . H11 H 0.2266 1.0107 0.5874 0.038(8) Uiso 1 1 calc R A . C12 C 0.0633(3) 0.9326(2) 0.57949(16) 0.0343(7) Uani 1 1 d . A . H121 H 0.0164 0.9649 0.5406 0.044(5) Uiso 1 1 calc R . . H122 H 0.0280 0.9467 0.6300 0.044(5) Uiso 1 1 calc R . . H123 H 0.0485 0.8742 0.5698 0.044(5) Uiso 1 1 calc R . . C13 C 0.2929(3) 0.90413(19) 0.63632(15) 0.0318(7) Uani 1 1 d . A . H131 H 0.3892 0.9178 0.6324 0.040(5) Uiso 1 1 calc R . . H132 H 0.2806 0.8453 0.6281 0.040(5) Uiso 1 1 calc R . . H133 H 0.2596 0.9189 0.6871 0.040(5) Uiso 1 1 calc R . . C31 C 0.2440(2) 0.88152(15) 0.32076(14) 0.0173(5) Uani 1 1 d . . . O31 O 0.24259(18) 0.91930(11) 0.26164(10) 0.0242(4) Uani 1 1 d . A . C32 C 0.1508(3) 0.80715(16) 0.33196(16) 0.0249(6) Uani 1 1 d . A . C33 C 0.0576(3) 0.80198(18) 0.26287(16) 0.0305(7) Uani 1 1 d . . . H331 H 0.1120 0.7960 0.2165 0.037(5) Uiso 1 1 calc R A . H332 H 0.0033 0.8520 0.2595 0.037(5) Uiso 1 1 calc R . . H333 H -0.0024 0.7546 0.2683 0.037(5) Uiso 1 1 calc R . . C34 C 0.2348(3) 0.72887(16) 0.33747(17) 0.0345(7) Uani 1 1 d . . . H341 H 0.2890 0.7225 0.2911 0.036(5) Uiso 1 1 calc R A . H342 H 0.1744 0.6817 0.3430 0.036(5) Uiso 1 1 calc R . . H343 H 0.2949 0.7322 0.3818 0.036(5) Uiso 1 1 calc R . . C35 C 0.0630(3) 0.81666(19) 0.40396(16) 0.0334(7) Uani 1 1 d . . . H351 H 0.0086 0.8666 0.3999 0.055(6) Uiso 1 1 calc R A . H352 H 0.1215 0.8202 0.4490 0.055(6) Uiso 1 1 calc R . . H353 H 0.0030 0.7692 0.4089 0.055(6) Uiso 1 1 calc R . . N40 N 0.1840(2) 1.04487(13) 0.42594(12) 0.0207(5) Uani 1 1 d . A . C41 C 0.1646(3) 1.08540(16) 0.35151(15) 0.0229(6) Uani 1 1 d . . . H41 H 0.2302 1.0624 0.3138 0.028(8) Uiso 1 1 calc R A . C42 C 0.1915(3) 1.17631(17) 0.36165(18) 0.0360(8) Uani 1 1 d . A . H421 H 0.2854 1.1845 0.3780 0.057(6) Uiso 1 1 calc R . . H422 H 0.1301 1.1985 0.4004 0.057(6) Uiso 1 1 calc R . . H423 H 0.1765 1.2046 0.3131 0.057(6) Uiso 1 1 calc R . . C43 C 0.0213(3) 1.06884(19) 0.32454(17) 0.0318(7) Uani 1 1 d . A . H431 H 0.0096 1.0100 0.3158 0.042(5) Uiso 1 1 calc R . . H432 H 0.0047 1.0985 0.2769 0.042(5) Uiso 1 1 calc R . . H433 H -0.0430 1.0873 0.3635 0.042(5) 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 0.0251(9) 0.0169(9) 0.0223(10) 0.0019(8) -0.0075(8) -0.0045(8) C2 0.0197(12) 0.0155(12) 0.0218(13) 0.0006(11) -0.0029(11) 0.0008(10) O3 0.028(5) 0.019(3) 0.022(3) 0.0003(13) -0.0047(12) -0.0058(14) C4 0.017(2) 0.017(2) 0.021(2) 0.004(2) 0.003(2) -0.004(2) O4 0.0296(19) 0.0272(16) 0.0176(16) 0.0089(15) -0.0018(16) -0.0095(15) C5 0.022(2) 0.021(2) 0.019(2) -0.0032(17) 0.002(2) -0.0048(18) C51 0.029(2) 0.019(2) 0.020(2) -0.0006(17) -0.0048(18) -0.0003(17) O51 0.0302(16) 0.0263(15) 0.0440(18) 0.0011(14) 0.0118(14) -0.0095(13) O52 0.0322(16) 0.0180(15) 0.0309(16) -0.0045(13) -0.0029(14) -0.0039(13) C52 0.037(3) 0.011(2) 0.050(4) -0.008(2) -0.011(3) 0.0002(19) C6 0.0183(13) 0.0188(13) 0.0267(15) -0.0007(12) -0.0052(11) -0.0035(11) C21 0.0178(13) 0.0272(15) 0.0378(16) -0.0050(14) 0.0040(13) 0.0032(12) C22 0.0184(14) 0.0427(19) 0.057(2) -0.0131(17) 0.0073(14) 0.0017(13) C23 0.0320(16) 0.0271(16) 0.062(2) -0.0031(16) -0.0019(16) 0.0143(14) C24 0.0308(15) 0.0363(17) 0.0378(17) -0.0175(15) 0.0087(14) 0.0034(14) C61 0.0254(14) 0.0262(14) 0.0250(14) -0.0004(13) -0.0070(12) -0.0060(12) C62 0.0281(15) 0.0359(16) 0.0286(15) 0.0001(14) -0.0098(13) -0.0062(13) C63 0.0360(16) 0.0304(16) 0.0346(17) 0.0093(14) -0.0156(14) -0.0058(14) C64 0.0384(17) 0.052(2) 0.0366(18) -0.0120(17) -0.0006(15) -0.0062(16) N10 0.0202(11) 0.0177(11) 0.0165(10) 0.0023(9) 0.0008(9) -0.0005(9) C20 0.0207(13) 0.0174(13) 0.0197(13) 0.0023(12) -0.0037(11) -0.0034(11) O20 0.0374(11) 0.0186(9) 0.0275(10) 0.0051(8) -0.0098(9) 0.0024(9) C30 0.0174(12) 0.0129(12) 0.0184(13) 0.0000(11) -0.0001(11) 0.0012(10) C40 0.0176(12) 0.0153(12) 0.0165(13) -0.0001(11) 0.0003(11) -0.0012(11) C11 0.0314(14) 0.0277(15) 0.0153(13) 0.0035(12) 0.0038(12) 0.0003(12) C12 0.0301(15) 0.0512(19) 0.0215(15) 0.0030(14) 0.0056(13) 0.0013(14) C13 0.0337(16) 0.0404(17) 0.0212(14) 0.0068(14) -0.0014(12) -0.0022(14) C31 0.0179(13) 0.0167(13) 0.0172(13) 0.0003(11) 0.0008(11) 0.0023(11) O31 0.0281(9) 0.0248(10) 0.0196(10) 0.0019(8) -0.0009(8) -0.0022(8) C32 0.0267(14) 0.0225(13) 0.0253(15) 0.0019(12) -0.0033(12) -0.0081(12) C33 0.0263(14) 0.0350(16) 0.0303(16) 0.0000(14) -0.0045(13) -0.0132(13) C34 0.0479(18) 0.0202(14) 0.0353(17) 0.0002(13) -0.0077(15) -0.0093(14) C35 0.0320(16) 0.0414(18) 0.0268(16) 0.0058(14) 0.0007(13) -0.0176(14) N40 0.0209(11) 0.0218(11) 0.0195(11) 0.0024(10) 0.0010(9) 0.0039(10) C41 0.0238(13) 0.0260(14) 0.0189(14) 0.0078(12) -0.0006(11) 0.0073(12) C42 0.055(2) 0.0221(15) 0.0313(17) 0.0082(13) -0.0065(15) 0.0117(14) C43 0.0287(14) 0.0404(18) 0.0263(15) 0.0095(14) 0.0003(13) 0.0064(14) _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 C6 1.348(3) . yes O1 C2 1.442(3) . yes C2 O3 1.423(3) . yes C2 O35 1.428(4) . ? C2 C21 1.564(4) . ? C2 C30 1.565(3) . yes O3 C4 1.371(5) . yes C4 O4 1.204(3) . yes C4 C5 1.446(4) . yes C5 C6 1.360(4) . yes C5 C51 1.503(5) . ? C51 O51 1.196(4) . ? C51 O52 1.339(4) . ? O52 C52 1.450(4) . ? C52 H521 0.9800 . ? C52 H522 0.9800 . ? C52 H523 0.9800 . ? O35 C45 1.375(6) . ? C45 O45 1.204(4) . ? C45 C55 1.443(5) . ? C55 C6 1.326(7) . ? C55 C56 1.502(6) . ? C56 O56 1.195(5) . ? C56 O57 1.338(5) . ? O57 C57 1.448(5) . ? C57 H571 0.9800 . ? C57 H572 0.9800 . ? C57 H573 0.9800 . ? C6 C61 1.526(4) . ? C21 C23 1.520(4) . ? C21 C24 1.534(4) . ? C21 C22 1.536(4) . ? C22 H221 0.9800 . ? C22 H222 0.9800 . ? C22 H223 0.9800 . ? C23 H231 0.9800 . ? C23 H232 0.9800 . ? C23 H233 0.9800 . ? C24 H241 0.9800 . ? C24 H242 0.9800 . ? C24 H243 0.9800 . ? C61 C63 1.525(4) . ? C61 C64 1.527(4) . ? C61 C62 1.531(4) . ? C62 H621 0.9800 . ? C62 H622 0.9800 . ? C62 H623 0.9800 . ? C63 H631 0.9800 . ? C63 H632 0.9800 . ? C63 H633 0.9800 . ? C64 H641 0.9800 . ? C64 H642 0.9800 . ? C64 H643 0.9800 . ? N10 C20 1.369(3) . yes N10 C40 1.408(3) . yes N10 C11 1.469(3) . yes C20 O20 1.198(3) . yes C20 C30 1.572(3) . yes C30 C31 1.557(3) . yes C30 C40 1.578(3) . yes C40 N40 1.244(3) . yes C11 C13 1.512(4) . ? C11 C12 1.527(4) . ? C11 H11 1.0000 . ? C12 H121 0.9800 . ? C12 H122 0.9800 . ? C12 H123 0.9800 . ? C13 H131 0.9800 . ? C13 H132 0.9800 . ? C13 H133 0.9800 . ? C31 O31 1.207(3) . yes C31 C32 1.537(4) . ? C32 C33 1.525(4) . ? C32 C34 1.528(4) . ? C32 C35 1.540(4) . ? C33 H331 0.9800 . ? C33 H332 0.9800 . ? C33 H333 0.9800 . ? C34 H341 0.9800 . ? C34 H342 0.9800 . ? C34 H343 0.9800 . ? C35 H351 0.9800 . ? C35 H352 0.9800 . ? C35 H353 0.9800 . ? N40 C41 1.476(3) . yes C41 C43 1.518(4) . ? C41 C42 1.519(4) . ? C41 H41 1.0000 . ? C42 H421 0.9800 . ? C42 H422 0.9800 . ? C42 H423 0.9800 . ? C43 H431 0.9800 . ? C43 H432 0.9800 . ? C43 H433 0.9800 . ? 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 O1 C2 123.42(19) . . yes O3 C2 O35 4.9(8) . . ? O1 C2 O3 114.5(2) . . yes O35 C2 O1 110.1(3) . . ? O3 C2 C21 107.8(7) . . ? O35 C2 C21 108.1(14) . . ? O35 C2 C30 109.5(14) . . ? O1 C2 C30 102.52(19) . . yes O1 C2 C21 107.00(19) . . ? O3 C2 C30 106.0(7) . . yes C21 C2 C30 119.3(2) . . ? C4 O3 C2 121.5(4) . . yes O4 C4 O3 116.9(3) . . yes O4 C4 C5 125.6(3) . . yes O3 C4 C5 117.4(3) . . yes C6 C5 C4 121.6(3) . . yes C4 C5 C51 113.3(3) . . yes C6 C5 C51 125.0(3) . . yes O51 C51 O52 124.4(3) . . ? O51 C51 C5 123.9(4) . . ? O52 C51 C5 111.6(3) . . ? C51 O52 C52 113.6(3) . . ? C45 O35 C2 126.5(5) . . ? O45 C45 O35 117.2(5) . . ? O45 C45 C55 126.2(5) . . ? O35 C45 C55 116.6(4) . . ? C6 C55 C45 118.1(4) . . ? C6 C55 C56 127.6(5) . . ? C45 C55 C56 114.2(5) . . ? O56 C56 O57 124.5(5) . . ? O56 C56 C55 124.0(5) . . ? O57 C56 C55 111.4(4) . . ? C56 O57 C57 114.0(5) . . ? O57 C57 H571 109.5 . . ? O57 C57 H572 109.5 . . ? H571 C57 H572 109.5 . . ? O57 C57 H573 109.5 . . ? H571 C57 H573 109.5 . . ? H572 C57 H573 109.5 . . ? C55 C6 O1 121.6(3) . . ? C55 C6 C5 21.6(4) . . ? O1 C6 C5 118.7(2) . . yes C55 C6 C61 123.6(3) . . ? O1 C6 C61 111.2(2) . . yes C5 C6 C61 130.0(2) . . yes C23 C21 C24 109.3(2) . . ? C23 C21 C22 108.7(2) . . ? C24 C21 C22 107.4(2) . . ? C23 C21 C2 111.4(2) . . ? C24 C21 C2 111.6(2) . . ? C22 C21 C2 108.3(2) . . ? C21 C22 H221 109.5 . . ? C21 C22 H222 109.5 . . ? H221 C22 H222 109.5 . . ? C21 C22 H223 109.5 . . ? H221 C22 H223 109.5 . . ? H222 C22 H223 109.5 . . ? C21 C23 H231 109.5 . . ? C21 C23 H232 109.5 . . ? H231 C23 H232 109.5 . . ? C21 C23 H233 109.5 . . ? H231 C23 H233 109.5 . . ? H232 C23 H233 109.5 . . ? C21 C24 H241 109.5 . . ? C21 C24 H242 109.5 . . ? H241 C24 H242 109.5 . . ? C21 C24 H243 109.5 . . ? H241 C24 H243 109.5 . . ? H242 C24 H243 109.5 . . ? C63 C61 C6 109.8(2) . . ? C63 C61 C64 109.8(2) . . ? C6 C61 C64 107.8(2) . . ? C63 C61 C62 108.3(2) . . ? C6 C61 C62 111.4(2) . . ? C64 C61 C62 109.7(2) . . ? C61 C62 H621 109.5 . . ? C61 C62 H622 109.5 . . ? H621 C62 H622 109.5 . . ? C61 C62 H623 109.5 . . ? H621 C62 H623 109.5 . . ? H622 C62 H623 109.5 . . ? C61 C63 H631 109.5 . . ? C61 C63 H632 109.5 . . ? H631 C63 H632 109.5 . . ? C61 C63 H633 109.5 . . ? H631 C63 H633 109.5 . . ? H632 C63 H633 109.5 . . ? C61 C64 H641 109.5 . . ? C61 C64 H642 109.5 . . ? H641 C64 H642 109.5 . . ? C61 C64 H643 109.5 . . ? H641 C64 H643 109.5 . . ? H642 C64 H643 109.5 . . ? C20 N10 C40 95.63(19) . . yes C20 N10 C11 135.0(2) . . yes C40 N10 C11 129.1(2) . . yes O20 C20 N10 132.0(2) . . yes O20 C20 C30 135.8(2) . . yes N10 C20 C30 92.19(19) . . yes C31 C30 C2 116.0(2) . . ? C31 C30 C20 120.44(19) . . ? C2 C30 C20 112.64(19) . . ? C31 C30 C40 108.57(18) . . ? C2 C30 C40 112.15(19) . . ? C20 C30 C40 81.59(18) . . yes N40 C40 N10 126.0(2) . . yes N40 C40 C30 143.4(2) . . yes N10 C40 C30 90.46(18) . . yes N10 C11 C13 111.0(2) . . ? N10 C11 C12 110.6(2) . . ? C13 C11 C12 112.2(2) . . ? N10 C11 H11 107.6 . . ? C13 C11 H11 107.6 . . ? C12 C11 H11 107.6 . . ? C11 C12 H121 109.5 . . ? C11 C12 H122 109.5 . . ? H121 C12 H122 109.5 . . ? C11 C12 H123 109.5 . . ? H121 C12 H123 109.5 . . ? H122 C12 H123 109.5 . . ? C11 C13 H131 109.5 . . ? C11 C13 H132 109.5 . . ? H131 C13 H132 109.5 . . ? C11 C13 H133 109.5 . . ? H131 C13 H133 109.5 . . ? H132 C13 H133 109.5 . . ? O31 C31 C32 120.5(2) . . ? O31 C31 C30 117.4(2) . . ? C32 C31 C30 122.0(2) . . ? C33 C32 C34 109.4(2) . . ? C33 C32 C31 107.7(2) . . ? C34 C32 C31 110.1(2) . . ? C33 C32 C35 108.4(2) . . ? C34 C32 C35 109.8(2) . . ? C31 C32 C35 111.3(2) . . ? C32 C33 H331 109.5 . . ? C32 C33 H332 109.5 . . ? H331 C33 H332 109.5 . . ? C32 C33 H333 109.5 . . ? H331 C33 H333 109.5 . . ? H332 C33 H333 109.5 . . ? C32 C34 H341 109.5 . . ? C32 C34 H342 109.5 . . ? H341 C34 H342 109.5 . . ? C32 C34 H343 109.5 . . ? H341 C34 H343 109.5 . . ? H342 C34 H343 109.5 . . ? C32 C35 H351 109.5 . . ? C32 C35 H352 109.5 . . ? H351 C35 H352 109.5 . . ? C32 C35 H353 109.5 . . ? H351 C35 H353 109.5 . . ? H352 C35 H353 109.5 . . ? C40 N40 C41 121.9(2) . . yes N40 C41 C43 108.5(2) . . ? N40 C41 C42 108.2(2) . . ? C43 C41 C42 112.0(2) . . ? N40 C41 H41 109.4 . . ? C43 C41 H41 109.4 . . ? C42 C41 H41 109.4 . . ? C41 C42 H421 109.5 . . ? C41 C42 H422 109.5 . . ? H421 C42 H422 109.5 . . ? C41 C42 H423 109.5 . . ? H421 C42 H423 109.5 . . ? H422 C42 H423 109.5 . . ? C41 C43 H431 109.5 . . ? C41 C43 H432 109.5 . . ? H431 C43 H432 109.5 . . ? C41 C43 H433 109.5 . . ? H431 C43 H433 109.5 . . ? H432 C43 H433 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 O1 C2 O3 -12.3(9) . . . . yes O1 C2 O3 C4 19.3(17) . . . . yes C2 O3 C4 C5 -12.5(18) . . . . yes O3 C4 C5 C6 -2.8(12) . . . . yes C4 C5 C6 O1 9.7(7) . . . . yes C5 C6 O1 C2 -1.7(4) . . . . yes C6 O1 C2 O35 -10.2(16) . . . . ? O1 C2 O35 C45 -2(4) . . . . ? C2 O35 C45 C55 2(4) . . . . ? O35 C45 C55 C6 9(2) . . . . ? C45 C55 C6 O1 -21.7(11) . . . . ? C55 C6 O1 C2 23.0(6) . . . . ? C6 O1 C2 C21 107.0(2) . . . . ? C6 O1 C2 C30 -126.6(2) . . . . ? O35 C2 O3 C4 -5(24) . . . . ? C21 C2 O3 C4 -99.6(13) . . . . ? C30 C2 O3 C4 131.6(13) . . . . ? C2 O3 C4 O4 169.9(10) . . . . yes O4 C4 C5 C6 174.6(6) . . . . ? O4 C4 C5 C51 -4.2(10) . . . . ? O3 C4 C5 C51 178.4(9) . . . . yes C6 C5 C51 O51 103.0(5) . . . . ? C4 C5 C51 O51 -78.2(6) . . . . yes C6 C5 C51 O52 -80.6(5) . . . . ? C4 C5 C51 O52 98.2(5) . . . . ? O51 C51 O52 C52 -1.8(6) . . . . ? C5 C51 O52 C52 -178.1(3) . . . . ? O3 C2 O35 C45 154(28) . . . . ? C21 C2 O35 C45 -119(3) . . . . ? C30 C2 O35 C45 110(3) . . . . ? C2 O35 C45 O45 -178(2) . . . . ? O45 C45 C55 C6 -169.8(14) . . . . ? O45 C45 C55 C56 10(2) . . . . ? O35 C45 C55 C56 -171(2) . . . . ? C6 C55 C56 O56 -72.8(12) . . . . ? C45 C55 C56 O56 107.9(12) . . . . ? C6 C55 C56 O57 104.6(9) . . . . ? C45 C55 C56 O57 -74.7(11) . . . . ? O56 C56 O57 C57 3.1(15) . . . . ? C55 C56 O57 C57 -174.3(10) . . . . ? C56 C55 C6 O1 159.1(5) . . . . ? C45 C55 C6 C5 66.9(11) . . . . ? C56 C55 C6 C5 -112.3(13) . . . . ? C45 C55 C6 C61 -178.2(9) . . . . ? C56 C55 C6 C61 2.6(10) . . . . ? C2 O1 C6 C61 -177.8(2) . . . . ? C4 C5 C6 C55 -94.2(10) . . . . ? C51 C5 C6 C55 84.5(9) . . . . ? C51 C5 C6 O1 -171.6(3) . . . . ? C4 C5 C6 C61 -175.1(5) . . . . ? C51 C5 C6 C61 3.6(7) . . . . ? O3 C2 C21 C23 -177.9(4) . . . . ? O35 C2 C21 C23 177.0(7) . . . . ? O1 C2 C21 C23 58.5(3) . . . . ? C30 C2 C21 C23 -57.1(3) . . . . ? O3 C2 C21 C24 -55.4(4) . . . . ? O35 C2 C21 C24 -60.5(7) . . . . ? O1 C2 C21 C24 -179.0(2) . . . . ? C30 C2 C21 C24 65.5(3) . . . . ? O3 C2 C21 C22 62.6(4) . . . . ? O35 C2 C21 C22 57.5(7) . . . . ? O1 C2 C21 C22 -61.0(3) . . . . ? C30 C2 C21 C22 -176.5(2) . . . . ? C55 C6 C61 C63 -177.0(5) . . . . ? O1 C6 C61 C63 24.3(3) . . . . ? C5 C6 C61 C63 -151.2(4) . . . . ? C55 C6 C61 C64 63.4(5) . . . . ? O1 C6 C61 C64 -95.3(3) . . . . ? C5 C6 C61 C64 89.2(4) . . . . ? C55 C6 C61 C62 -57.1(6) . . . . ? O1 C6 C61 C62 144.3(2) . . . . ? C5 C6 C61 C62 -31.2(5) . . . . ? C40 N10 C20 O20 -176.3(3) . . . . ? C11 N10 C20 O20 -2.9(5) . . . . yes C40 N10 C20 C30 2.91(19) . . . . ? C11 N10 C20 C30 176.3(3) . . . . ? C21 C2 C30 C31 -60.5(3) . . . . ? C21 C2 C30 C20 84.0(3) . . . . ? O1 C2 C30 C40 56.0(2) . . . . ? O3 C2 C30 C40 -64.3(4) . . . . ? C21 C2 C30 C40 174.0(2) . . . . yes O35 C2 C30 C31 64.7(7) . . . . ? O1 C2 C30 C31 -178.41(18) . . . . yes O3 C2 C30 C31 61.2(5) . . . . yes O35 C2 C30 C40 -60.8(8) . . . . ? O35 C2 C30 C20 -150.7(7) . . . . ? O1 C2 C30 C20 -33.9(2) . . . . yes O3 C2 C30 C20 -154.2(4) . . . . yes O20 C20 C30 C31 69.9(4) . . . . ? N10 C20 C30 C31 -109.3(2) . . . . ? O20 C20 C30 C2 -72.9(4) . . . . ? N10 C20 C30 C2 108.0(2) . . . . ? O20 C20 C30 C40 176.5(3) . . . . yes N10 C20 C30 C40 -2.61(17) . . . . yes C20 N10 C40 N40 173.9(2) . . . . ? C11 N10 C40 N40 -0.1(4) . . . . yes C20 N10 C40 C30 -2.89(19) . . . . ? C11 N10 C40 C30 -176.9(2) . . . . ? C31 C30 C40 N40 -53.8(4) . . . . ? C2 C30 C40 N40 75.8(4) . . . . ? C20 C30 C40 N40 -173.1(4) . . . . ? C31 C30 C40 N10 121.91(19) . . . . ? C2 C30 C40 N10 -108.6(2) . . . . ? C20 C30 C40 N10 2.54(17) . . . . ? C20 N10 C11 C13 26.9(4) . . . . ? C40 N10 C11 C13 -161.6(2) . . . . ? C20 N10 C11 C12 -98.3(3) . . . . ? C40 N10 C11 C12 73.2(3) . . . . ? C2 C30 C31 O31 -41.3(3) . . . . ? C20 C30 C31 O31 177.1(2) . . . . ? C40 C30 C31 O31 86.0(3) . . . . ? C2 C30 C31 C32 143.4(2) . . . . ? C20 C30 C31 C32 1.8(3) . . . . ? C40 C30 C31 C32 -89.3(3) . . . . ? O31 C31 C32 C33 -6.4(3) . . . . ? C30 C31 C32 C33 168.7(2) . . . . ? O31 C31 C32 C34 112.9(3) . . . . ? C30 C31 C32 C34 -72.0(3) . . . . ? O31 C31 C32 C35 -125.1(3) . . . . ? C30 C31 C32 C35 50.0(3) . . . . ? N10 C40 N40 C41 -176.0(2) . . . . yes C30 C40 N40 C41 -1.4(5) . . . . ? C40 N40 C41 C43 105.1(3) . . . . ? C40 N40 C41 C42 -133.2(3) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.169 _refine_diff_density_min -0.145 _refine_diff_density_rms 0.036