data_global _journal_coden_Cambridge 182 _publ_requested_journal 'Chemical Communications' loop_ _publ_author_name 'Russell Cox' 'A. S. Evitt' _publ_contact_author_name 'Russell Cox ' _publ_contact_author_address ; School of Chemistry University of Bristol Cantocks Close Bristol BS8 1TS UNITED KINGDOM ; _publ_contact_author_email R.J.COX@BRISTOL.AC.UK _publ_section_title ; Acyl Palladium Species in Synthesis: Single Step Synthesis of ?,?-Unsaturated Ketones from Acid Chlorides ; data_aseiv80amu _database_code_depnum_ccdc_archive 'CCDC 622616' _audit_creation_method SHELXL-97 _chemical_formula_moiety 'C13 H15 N O3' _chemical_formula_sum 'C13 H15 N O3' _chemical_formula_weight 233.26 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.2761(17) _cell_length_b 10.042(2) _cell_length_c 15.189(3) _cell_angle_alpha 74.44(3) _cell_angle_beta 81.70(3) _cell_angle_gamma 82.47(3) _cell_volume 1197.7(5) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 1026 _cell_measurement_theta_min 2.8185 _cell_measurement_theta_max 22.9855 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.294 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 496 _exptl_absorpt_coefficient_mu 0.092 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.86 _exptl_absorpt_correction_T_max 1.00 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'Bruker-AXS D8' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 8.366 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 13744 _diffrn_reflns_av_R_equivalents 0.0676 _diffrn_reflns_av_sigmaI/netI 0.0956 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.40 _diffrn_reflns_theta_max 27.48 _reflns_number_total 5466 _reflns_number_gt 4029 _reflns_threshold_expression >2\s(I) _computing_data_collection 'SMART v5.628 (Bruker-AXS, 1997-2002)' _computing_cell_refinement 'SMART v5.628 (Bruker-AXS, 1997-2002)' _computing_data_reduction ; SAINT v7.06A (Bruker-AXS, 1997-2003) & SHELXTL v6.14 (Bruker-AXS, 2003) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0641P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5466 _refine_ls_number_parameters 311 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1605 _refine_ls_R_factor_gt 0.1222 _refine_ls_wR_factor_ref 0.2285 _refine_ls_wR_factor_gt 0.2105 _refine_ls_goodness_of_fit_ref 1.482 _refine_ls_restrained_S_all 1.482 _refine_ls_shift/su_max 0.035 _refine_ls_shift/su_mean 0.009 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 C1 C 0.9049(5) 0.2921(4) 0.7124(2) 0.0166(8) Uani 1 1 d . . . H1A H 0.8780 0.3626 0.7446 0.020 Uiso 1 1 calc R . . C2 C 1.0028(5) 0.3196(4) 0.6296(2) 0.0140(8) Uani 1 1 d . . . H2A H 1.0422 0.4081 0.6036 0.017 Uiso 1 1 calc R . . C3 C 1.0420(4) 0.2132(4) 0.5854(2) 0.0130(8) Uani 1 1 d . . . C4 C 0.9828(5) 0.0844(4) 0.6192(2) 0.0155(8) Uani 1 1 d . . . H4 H 1.0107 0.0142 0.5869 0.019 Uiso 1 1 calc R . . C5 C 0.8816(5) 0.0610(4) 0.7018(2) 0.0175(8) Uani 1 1 d . . . H5 H 0.8372 -0.0258 0.7257 0.021 Uiso 1 1 calc R . . C6 C 0.8441(4) 0.1631(4) 0.7504(2) 0.0149(8) Uani 1 1 d . . . C7 C 0.7270(5) 0.1307(4) 0.8371(2) 0.0215(9) Uani 1 1 d . . . C8 C 0.7462(5) 0.1862(4) 0.9164(2) 0.0210(9) Uani 1 1 d . . . C9 C 0.8908(5) 0.2230(4) 0.9249(3) 0.0248(10) Uani 1 1 d . . . H9 H 0.9757 0.2170 0.8765 0.030 Uiso 1 1 calc R . . C10 C 0.9353(6) 0.2731(5) 1.0023(3) 0.0329(11) Uani 1 1 d . . . H10A H 0.9834 0.3627 0.9770 0.039 Uiso 1 1 calc R . . H10B H 0.8351 0.2886 1.0440 0.039 Uiso 1 1 calc R . . C11 C 1.0564(6) 0.1690(5) 1.0556(3) 0.0307(11) Uani 1 1 d . . . H11A H 1.0060 0.0823 1.0842 0.046 Uiso 1 1 calc R . . H11B H 1.0882 0.2058 1.1035 0.046 Uiso 1 1 calc R . . H11C H 1.1538 0.1510 1.0139 0.046 Uiso 1 1 calc R . . C12 C 0.5960(6) 0.1883(5) 0.9861(3) 0.0350(12) Uani 1 1 d . . . H12A H 0.5305 0.1122 0.9868 0.042 Uiso 1 1 calc R . . H12B H 0.6313 0.1712 1.0480 0.042 Uiso 1 1 calc R . . C13 C 0.4907(6) 0.3229(5) 0.9657(3) 0.0377(12) Uani 1 1 d . . . H13A H 0.5543 0.3985 0.9659 0.057 Uiso 1 1 calc R . . H13B H 0.3957 0.3193 1.0127 0.057 Uiso 1 1 calc R . . H13C H 0.4529 0.3393 0.9051 0.057 Uiso 1 1 calc R . . C14 C 0.5603(5) 0.1416(4) 0.5374(2) 0.0153(8) Uani 1 1 d . . . H14 H 0.5851 0.0802 0.4984 0.018 Uiso 1 1 calc R . . C15 C 0.4614(5) 0.1025(4) 0.6192(2) 0.0145(8) Uani 1 1 d . . . H15 H 0.4191 0.0144 0.6376 0.017 Uiso 1 1 calc R . . C16 C 0.4254(5) 0.1957(4) 0.6738(2) 0.0166(8) Uani 1 1 d . . . C17 C 0.4889(5) 0.3231(4) 0.6508(2) 0.0159(8) Uani 1 1 d . . . H17 H 0.4637 0.3842 0.6900 0.019 Uiso 1 1 calc R . . C18 C 0.5898(5) 0.3586(4) 0.5693(2) 0.0144(8) Uani 1 1 d . . . H18 H 0.6362 0.4448 0.5526 0.017 Uiso 1 1 calc R . . C19 C 0.6250(4) 0.2704(4) 0.5109(2) 0.0109(7) Uani 1 1 d . . . C20 C 0.7364(5) 0.3121(4) 0.4228(2) 0.0135(8) Uani 1 1 d . . . C21 C 0.7001(4) 0.2848(3) 0.3368(2) 0.0117(8) Uani 1 1 d . . . C22 C 0.5453(5) 0.2760(4) 0.3247(2) 0.0127(8) Uani 1 1 d . . . H22 H 0.4657 0.2752 0.3765 0.015 Uiso 1 1 calc R . . C23 C 0.4834(5) 0.2672(4) 0.2392(2) 0.0170(8) Uani 1 1 d . . . H23A H 0.4613 0.1704 0.2453 0.020 Uiso 1 1 calc R . . H23B H 0.5686 0.2927 0.1864 0.020 Uiso 1 1 calc R . . C24 C 0.3271(5) 0.3632(5) 0.2206(3) 0.0309(11) Uani 1 1 d . . . H24A H 0.2437 0.3403 0.2736 0.046 Uiso 1 1 calc R . . H24B H 0.2864 0.3515 0.1659 0.046 Uiso 1 1 calc R . . H24C H 0.3504 0.4598 0.2101 0.031 Uiso 1 1 calc R . . C25 C 0.8448(4) 0.2860(4) 0.2627(2) 0.0135(8) Uani 1 1 d . . . H25A H 0.8288 0.2234 0.2249 0.016 Uiso 1 1 calc R . . H25B H 0.9462 0.2496 0.2924 0.016 Uiso 1 1 calc R . . C26 C 0.8660(5) 0.4313(4) 0.2003(2) 0.0207(9) Uani 1 1 d . . . H26A H 0.7691 0.4653 0.1675 0.031 Uiso 1 1 calc R . . H26B H 0.9636 0.4275 0.1557 0.031 Uiso 1 1 calc R . . H26C H 0.8791 0.4942 0.2376 0.031 Uiso 1 1 calc R . . N1 N 1.1478(4) 0.2404(3) 0.49796(19) 0.0127(7) Uani 1 1 d . . . N2 N 0.3160(4) 0.1554(3) 0.7604(2) 0.0171(7) Uani 1 1 d . . . O1 O 1.1740(3) 0.1497(3) 0.45524(17) 0.0197(6) Uani 1 1 d . . . O2 O 1.2077(3) 0.3516(3) 0.47029(16) 0.0173(6) Uani 1 1 d . . . O3 O 0.6188(3) 0.0572(3) 0.84146(18) 0.0242(7) Uani 1 1 d . . . O4 O 0.2849(3) 0.2381(3) 0.80854(18) 0.0253(7) Uani 1 1 d . . . O5 O 0.2613(3) 0.0428(3) 0.78001(17) 0.0235(7) Uani 1 1 d . . . O6 O 0.8577(3) 0.3701(3) 0.42335(17) 0.0178(6) Uani 1 1 d . . . 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 C1 0.018(2) 0.0148(19) 0.0183(19) -0.0078(15) -0.0007(16) 0.0013(16) C2 0.015(2) 0.0119(18) 0.0167(18) -0.0047(15) -0.0019(15) -0.0048(15) C3 0.0097(19) 0.0170(19) 0.0110(17) -0.0020(14) -0.0003(14) -0.0012(15) C4 0.018(2) 0.0151(19) 0.0147(18) -0.0060(15) -0.0044(15) -0.0006(16) C5 0.019(2) 0.018(2) 0.0158(19) -0.0021(15) -0.0039(16) -0.0064(17) C6 0.0122(19) 0.022(2) 0.0096(17) -0.0024(15) -0.0033(14) -0.0004(16) C7 0.018(2) 0.026(2) 0.0133(19) 0.0029(16) -0.0007(16) 0.0037(18) C8 0.027(2) 0.022(2) 0.0098(18) -0.0028(15) 0.0028(16) 0.0046(18) C9 0.027(2) 0.033(2) 0.014(2) -0.0095(17) -0.0034(17) 0.007(2) C10 0.048(3) 0.033(3) 0.017(2) -0.0087(19) -0.005(2) 0.001(2) C11 0.036(3) 0.038(3) 0.022(2) -0.0147(19) -0.007(2) 0.002(2) C12 0.043(3) 0.035(3) 0.025(2) -0.013(2) 0.018(2) -0.012(2) C13 0.026(3) 0.050(3) 0.044(3) -0.033(2) 0.004(2) 0.003(2) C14 0.020(2) 0.0162(19) 0.0137(18) -0.0104(15) -0.0010(15) -0.0034(16) C15 0.017(2) 0.0121(18) 0.0164(18) -0.0043(15) -0.0027(15) -0.0052(15) C16 0.015(2) 0.022(2) 0.0145(18) -0.0054(15) -0.0057(15) -0.0006(16) C17 0.020(2) 0.0138(19) 0.0177(19) -0.0089(15) -0.0084(16) 0.0015(16) C18 0.019(2) 0.0111(18) 0.0149(18) -0.0030(14) -0.0057(15) -0.0036(15) C19 0.0102(18) 0.0102(18) 0.0126(17) -0.0017(14) -0.0033(14) -0.0028(14) C20 0.015(2) 0.0077(17) 0.0174(18) -0.0027(14) -0.0035(15) 0.0010(15) C21 0.0139(19) 0.0057(17) 0.0142(18) -0.0027(14) -0.0006(14) 0.0028(14) C22 0.017(2) 0.0082(17) 0.0125(17) -0.0039(14) 0.0032(14) -0.0013(15) C23 0.022(2) 0.018(2) 0.0157(18) -0.0097(15) -0.0040(15) -0.0051(17) C24 0.021(2) 0.054(3) 0.017(2) -0.007(2) -0.0055(17) 0.002(2) C25 0.0102(19) 0.0131(18) 0.0154(18) -0.0033(14) 0.0028(14) 0.0006(15) C26 0.023(2) 0.022(2) 0.0147(19) -0.0024(16) 0.0057(16) -0.0073(18) N1 0.0088(16) 0.0197(17) 0.0114(15) -0.0075(13) 0.0028(12) -0.0050(13) N2 0.0174(18) 0.0213(18) 0.0140(16) -0.0070(14) -0.0019(13) -0.0011(14) O1 0.0279(17) 0.0176(14) 0.0176(14) -0.0145(11) 0.0053(12) -0.0044(12) O2 0.0178(15) 0.0173(14) 0.0186(14) -0.0081(11) 0.0069(11) -0.0104(12) O3 0.0153(15) 0.0358(18) 0.0177(14) 0.0031(12) -0.0019(11) -0.0098(13) O4 0.0273(17) 0.0297(17) 0.0222(15) -0.0179(13) 0.0072(12) -0.0018(14) O5 0.0270(17) 0.0251(16) 0.0186(14) -0.0045(12) 0.0003(12) -0.0086(13) O6 0.0153(14) 0.0198(15) 0.0186(14) -0.0019(11) -0.0038(11) -0.0070(12) _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 C1 C2 1.377(5) . ? C1 C6 1.397(5) . ? C1 H1A 0.9500 . ? C2 C3 1.389(5) . ? C2 H2A 0.9500 . ? C3 C4 1.383(5) . ? C3 N1 1.462(4) . ? C4 C5 1.386(5) . ? C4 H4 0.9500 . ? C5 C6 1.396(5) . ? C5 H5 0.9500 . ? C6 C7 1.504(5) . ? C7 O3 1.217(5) . ? C7 C8 1.492(5) . ? C8 C9 1.331(6) . ? C8 C12 1.514(6) . ? C9 C10 1.504(5) . ? C9 H9 0.9500 . ? C10 C11 1.502(6) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 C13 1.492(6) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 C15 1.376(5) . ? C14 C19 1.401(5) . ? C14 H14 0.9500 . ? C15 C16 1.388(5) . ? C15 H15 0.9500 . ? C16 C17 1.385(5) . ? C16 N2 1.477(5) . ? C17 C18 1.378(5) . ? C17 H17 0.9500 . ? C18 C19 1.390(5) . ? C18 H18 0.9500 . ? C19 C20 1.504(5) . ? C20 O6 1.227(4) . ? C20 C21 1.483(5) . ? C21 C22 1.338(5) . ? C21 C25 1.518(5) . ? C22 C23 1.491(5) . ? C22 H22 0.9500 . ? C23 C24 1.522(6) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C25 C26 1.529(5) . ? C25 H25A 0.9900 . ? C25 H25B 0.9900 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? N1 O2 1.226(4) . ? N1 O1 1.233(4) . ? N2 O5 1.219(4) . ? N2 O4 1.227(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 C2 C1 C6 121.6(3) . . ? C2 C1 H1A 119.2 . . ? C6 C1 H1A 119.2 . . ? C1 C2 C3 117.6(3) . . ? C1 C2 H2A 121.2 . . ? C3 C2 H2A 121.2 . . ? C4 C3 C2 123.1(3) . . ? C4 C3 N1 118.8(3) . . ? C2 C3 N1 118.1(3) . . ? C3 C4 C5 117.9(3) . . ? C3 C4 H4 121.0 . . ? C5 C4 H4 121.0 . . ? C4 C5 C6 120.9(3) . . ? C4 C5 H5 119.5 . . ? C6 C5 H5 119.5 . . ? C5 C6 C1 118.8(3) . . ? C5 C6 C7 117.1(3) . . ? C1 C6 C7 123.8(3) . . ? O3 C7 C8 121.0(3) . . ? O3 C7 C6 118.8(4) . . ? C8 C7 C6 120.1(4) . . ? C9 C8 C7 120.2(4) . . ? C9 C8 C12 124.2(4) . . ? C7 C8 C12 115.5(4) . . ? C8 C9 C10 127.6(4) . . ? C8 C9 H9 116.2 . . ? C10 C9 H9 116.2 . . ? C11 C10 C9 110.8(4) . . ? C11 C10 H10A 109.5 . . ? C9 C10 H10A 109.5 . . ? C11 C10 H10B 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 108.1 . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C13 C12 C8 112.5(4) . . ? C13 C12 H12A 109.1 . . ? C8 C12 H12A 109.1 . . ? C13 C12 H12B 109.1 . . ? C8 C12 H12B 109.1 . . ? H12A C12 H12B 107.8 . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C15 C14 C19 121.1(3) . . ? C15 C14 H14 119.5 . . ? C19 C14 H14 119.5 . . ? C14 C15 C16 117.9(3) . . ? C14 C15 H15 121.0 . . ? C16 C15 H15 121.0 . . ? C17 C16 C15 122.8(3) . . ? C17 C16 N2 119.2(3) . . ? C15 C16 N2 118.0(3) . . ? C18 C17 C16 118.0(3) . . ? C18 C17 H17 121.0 . . ? C16 C17 H17 121.0 . . ? C17 C18 C19 121.2(3) . . ? C17 C18 H18 119.4 . . ? C19 C18 H18 119.4 . . ? C18 C19 C14 119.0(3) . . ? C18 C19 C20 119.7(3) . . ? C14 C19 C20 121.3(3) . . ? O6 C20 C21 120.6(3) . . ? O6 C20 C19 118.6(3) . . ? C21 C20 C19 120.9(3) . . ? C22 C21 C20 120.0(3) . . ? C22 C21 C25 124.2(3) . . ? C20 C21 C25 115.3(3) . . ? C21 C22 C23 127.5(3) . . ? C21 C22 H22 116.3 . . ? C23 C22 H22 116.3 . . ? C22 C23 C24 111.5(3) . . ? C22 C23 H23A 109.3 . . ? C24 C23 H23A 109.3 . . ? C22 C23 H23B 109.3 . . ? C24 C23 H23B 109.3 . . ? H23A C23 H23B 108.0 . . ? C23 C24 H24A 109.5 . . ? C23 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C23 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C21 C25 C26 112.5(3) . . ? C21 C25 H25A 109.1 . . ? C26 C25 H25A 109.1 . . ? C21 C25 H25B 109.1 . . ? C26 C25 H25B 109.1 . . ? H25A C25 H25B 107.8 . . ? C25 C26 H26A 109.5 . . ? C25 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C25 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? O2 N1 O1 122.6(3) . . ? O2 N1 C3 118.9(3) . . ? O1 N1 C3 118.5(3) . . ? O5 N2 O4 123.7(3) . . ? O5 N2 C16 118.6(3) . . ? O4 N2 C16 117.8(3) . . ? 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 C1 C2 C3 -1.1(5) . . . . ? C1 C2 C3 C4 2.3(6) . . . . ? C1 C2 C3 N1 -179.2(3) . . . . ? C2 C3 C4 C5 -0.9(5) . . . . ? N1 C3 C4 C5 -179.5(3) . . . . ? C3 C4 C5 C6 -1.6(5) . . . . ? C4 C5 C6 C1 2.7(6) . . . . ? C4 C5 C6 C7 177.2(3) . . . . ? C2 C1 C6 C5 -1.3(6) . . . . ? C2 C1 C6 C7 -175.4(4) . . . . ? C5 C6 C7 O3 -32.4(5) . . . . ? C1 C6 C7 O3 141.9(4) . . . . ? C5 C6 C7 C8 146.6(4) . . . . ? C1 C6 C7 C8 -39.2(5) . . . . ? O3 C7 C8 C9 156.4(4) . . . . ? C6 C7 C8 C9 -22.5(6) . . . . ? O3 C7 C8 C12 -20.1(6) . . . . ? C6 C7 C8 C12 161.0(4) . . . . ? C7 C8 C9 C10 -176.3(4) . . . . ? C12 C8 C9 C10 -0.1(7) . . . . ? C8 C9 C10 C11 112.6(5) . . . . ? C9 C8 C12 C13 91.4(5) . . . . ? C7 C8 C12 C13 -92.2(5) . . . . ? C19 C14 C15 C16 1.1(6) . . . . ? C14 C15 C16 C17 -2.2(6) . . . . ? C14 C15 C16 N2 178.5(3) . . . . ? C15 C16 C17 C18 1.1(6) . . . . ? N2 C16 C17 C18 -179.6(3) . . . . ? C16 C17 C18 C19 1.0(5) . . . . ? C17 C18 C19 C14 -2.0(5) . . . . ? C17 C18 C19 C20 -179.7(3) . . . . ? C15 C14 C19 C18 0.9(6) . . . . ? C15 C14 C19 C20 178.5(3) . . . . ? C18 C19 C20 O6 39.9(5) . . . . ? C14 C19 C20 O6 -137.7(4) . . . . ? C18 C19 C20 C21 -139.7(4) . . . . ? C14 C19 C20 C21 42.7(5) . . . . ? O6 C20 C21 C22 -152.8(4) . . . . ? C19 C20 C21 C22 26.8(5) . . . . ? O6 C20 C21 C25 20.2(5) . . . . ? C19 C20 C21 C25 -160.3(3) . . . . ? C20 C21 C22 C23 171.6(3) . . . . ? C25 C21 C22 C23 -0.6(6) . . . . ? C21 C22 C23 C24 -135.4(4) . . . . ? C22 C21 C25 C26 85.1(4) . . . . ? C20 C21 C25 C26 -87.5(4) . . . . ? C4 C3 N1 O2 -176.0(3) . . . . ? C2 C3 N1 O2 5.3(5) . . . . ? C4 C3 N1 O1 3.5(5) . . . . ? C2 C3 N1 O1 -175.1(3) . . . . ? C17 C16 N2 O5 -179.8(3) . . . . ? C15 C16 N2 O5 -0.5(5) . . . . ? C17 C16 N2 O4 0.5(5) . . . . ? C15 C16 N2 O4 179.8(3) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.473 _refine_diff_density_min -0.635 _refine_diff_density_rms 0.104