#------------------------------------------------------------------------------ #$Date: 2012-06-14 10:54:38 +0300 (Thu, 14 Jun 2012) $ #$Revision: 60034 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/23/45/2234563.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2234563 loop_ _publ_author_name 'He, Yan-Qin' 'Chen, Jin-Quan' _publ_section_title ; Diethyl 4-methoxyoxalyl-3,5-diphenylpyrrolidine-2,2-dicarboxylate ; _journal_coeditor_code CV5272 _journal_issue 5 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o1325 _journal_volume 68 _journal_year 2012 _chemical_formula_iupac 'C25 H27 N O7' _chemical_formula_moiety 'C25 H27 N O7' _chemical_formula_sum 'C25 H27 N O7' _chemical_formula_weight 453.48 _chemical_name_systematic ; Diethyl 4-methoxyoxalyl-3,5-diphenylpyrrolidine-2,2-dicarboxylate ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 102.213(3) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 8.8779(3) _cell_length_b 20.3438(6) _cell_length_c 13.5740(5) _cell_measurement_reflns_used 4380 _cell_measurement_temperature 290(2) _cell_measurement_theta_max 29.0464 _cell_measurement_theta_min 3.2115 _cell_volume 2396.12(14) _computing_cell_refinement 'CrysAlis PRO (Oxford Diffraction, 2010)' _computing_data_collection 'CrysAlis PRO (Oxford Diffraction, 2010)' _computing_data_reduction 'CrysAlis PRO (Oxford Diffraction, 2010)' _computing_molecular_graphics 'XP in SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXL97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _diffrn_ambient_temperature 290(2) _diffrn_detector_area_resol_mean 15.9149 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_device_type 'Oxford Diffraction Gemini S Ultra' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0330 _diffrn_reflns_av_sigmaI/netI 0.0405 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 14990 _diffrn_reflns_theta_full 26.37 _diffrn_reflns_theta_max 26.37 _diffrn_reflns_theta_min 3.22 _exptl_absorpt_coefficient_mu 0.092 _exptl_absorpt_correction_T_max 0.9729 _exptl_absorpt_correction_T_min 0.9659 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; (CrysAlis PRO; Oxford Diffraction, 2010) ; _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.257 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 960 _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.30 _refine_diff_density_max 0.279 _refine_diff_density_min -0.261 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.018 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 305 _refine_ls_number_reflns 4887 _refine_ls_number_restraints 8 _refine_ls_restrained_S_all 1.127 _refine_ls_R_factor_all 0.0920 _refine_ls_R_factor_gt 0.0514 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0554P)^2^+0.3662P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1136 _refine_ls_wR_factor_ref 0.1334 _reflns_number_gt 3129 _reflns_number_total 4887 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file cv5272.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'P 21/c' _cod_database_code 2234563 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' loop_ _atom_site_type_symbol _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_symmetry_multiplicity N N1 0.9482(2) 0.04749(8) 0.86894(15) 0.0445(4) Uani d D 1 1 O O1 0.75874(18) 0.01366(7) 1.00477(12) 0.0587(4) Uani d . 1 1 O O2 0.68505(17) 0.11814(7) 1.01209(11) 0.0537(4) Uani d . 1 1 O O3 0.90888(18) 0.20277(8) 0.85551(13) 0.0627(5) Uani d . 1 1 O O4 0.99367(18) 0.16006(7) 1.00924(12) 0.0606(5) Uani d . 1 1 O O5 0.6663(2) 0.05129(8) 0.58463(13) 0.0646(5) Uani d . 1 1 O O6 0.5961(2) -0.10174(9) 0.66768(15) 0.0833(6) Uani d . 1 1 O O7 0.6680(2) -0.07505(8) 0.52526(13) 0.0672(5) Uani d . 1 1 C C2 0.8329(2) 0.09267(9) 0.89093(15) 0.0390(5) Uani d . 1 1 C C3 0.7135(2) 0.09231(9) 0.78941(15) 0.0393(5) Uani d . 1 1 H H3 0.7590 0.1168 0.7408 0.047 Uiso calc R 1 1 C C4 0.7112(2) 0.01965(9) 0.75916(16) 0.0416(5) Uani d . 1 1 H H4 0.6324 -0.0027 0.7877 0.050 Uiso calc R 1 1 C C5 0.8726(2) -0.00897(10) 0.81100(16) 0.0427(5) Uani d . 1 1 H H5 0.8575 -0.0436 0.8582 0.051 Uiso calc R 1 1 C C6 0.7574(2) 0.06980(10) 0.97687(16) 0.0418(5) Uani d . 1 1 C C7 0.5949(3) 0.10022(14) 1.0861(2) 0.0740(8) Uani d U 1 1 H H7A 0.5254 0.0644 1.0608 0.089 Uiso calc R 1 1 H H7B 0.6625 0.0862 1.1483 0.089 Uiso calc R 1 1 C C8 0.5078(5) 0.15783(19) 1.1041(3) 0.1267(13) Uani d U 1 1 H H8A 0.4510 0.1746 1.0409 0.190 Uiso calc R 1 1 H H8B 0.5773 0.1910 1.1372 0.190 Uiso calc R 1 1 H H8C 0.4374 0.1460 1.1460 0.190 Uiso calc R 1 1 C C9 0.9123(2) 0.15908(11) 0.91495(18) 0.0453(5) Uani d . 1 1 C C10 1.0665(3) 0.22220(14) 1.0448(2) 0.0809(9) Uani d . 1 1 H H10A 1.1018 0.2439 0.9902 0.097 Uiso calc R 1 1 H H10B 1.1555 0.2140 1.0986 0.097 Uiso calc R 1 1 C C11 0.9557(4) 0.26554(15) 1.0823(3) 0.1000(11) Uani d . 1 1 H H11A 0.8684 0.2741 1.0287 0.150 Uiso calc R 1 1 H H11B 1.0053 0.3063 1.1056 0.150 Uiso calc R 1 1 H H11C 0.9219 0.2442 1.1369 0.150 Uiso calc R 1 1 C C12 0.5595(2) 0.12441(10) 0.79130(15) 0.0412(5) Uani d . 1 1 C C13 0.4339(2) 0.09043(12) 0.81017(19) 0.0570(6) Uani d . 1 1 H H13 0.4396 0.0450 0.8180 0.068 Uiso calc R 1 1 C C14 0.3000(3) 0.12289(14) 0.8176(2) 0.0704(7) Uani d . 1 1 H H14 0.2169 0.0991 0.8307 0.084 Uiso calc R 1 1 C C15 0.2887(3) 0.18935(14) 0.8060(2) 0.0683(7) Uani d . 1 1 H H15 0.1988 0.2110 0.8118 0.082 Uiso calc R 1 1 C C16 0.4104(3) 0.22371(13) 0.7859(2) 0.0671(7) Uani d . 1 1 H H16 0.4033 0.2691 0.7776 0.080 Uiso calc R 1 1 C C17 0.5440(3) 0.19164(10) 0.77789(18) 0.0545(6) Uani d . 1 1 H H17 0.6255 0.2157 0.7631 0.065 Uiso calc R 1 1 C C18 0.6739(2) 0.00889(10) 0.64679(17) 0.0459(5) Uani d . 1 1 C C19 0.6410(3) -0.06290(12) 0.61527(19) 0.0533(6) Uani d . 1 1 C C20 0.6394(4) -0.14192(14) 0.4894(2) 0.0933(10) Uani d . 1 1 H H20A 0.6611 -0.1457 0.4232 0.140 Uiso calc R 1 1 H H20B 0.5335 -0.1530 0.4866 0.140 Uiso calc R 1 1 H H20C 0.7048 -0.1714 0.5345 0.140 Uiso calc R 1 1 C C21 0.9705(2) -0.03601(10) 0.74167(17) 0.0466(5) Uani d . 1 1 C C22 0.9944(3) -0.10277(12) 0.7365(2) 0.0651(7) Uani d . 1 1 H H22 0.9494 -0.1311 0.7757 0.078 Uiso calc R 1 1 C C23 1.0847(4) -0.12831(15) 0.6737(2) 0.0820(9) Uani d . 1 1 H H23 1.0998 -0.1734 0.6709 0.098 Uiso calc R 1 1 C C24 1.1512(4) -0.08695(18) 0.6163(2) 0.0861(9) Uani d . 1 1 H H24 1.2127 -0.1040 0.5748 0.103 Uiso calc R 1 1 C C25 1.1283(3) -0.02117(16) 0.6190(2) 0.0783(8) Uani d . 1 1 H H25 1.1730 0.0067 0.5790 0.094 Uiso calc R 1 1 C C26 1.0380(3) 0.00470(12) 0.68185(19) 0.0611(6) Uani d . 1 1 H H26 1.0228 0.0499 0.6836 0.073 Uiso calc R 1 1 H H1N 1.016(2) 0.0357(10) 0.9232(14) 0.054(7) Uiso d D 1 1 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 N1 0.0426(10) 0.0438(10) 0.0464(12) 0.0056(8) 0.0077(9) -0.0022(9) O1 0.0719(11) 0.0459(9) 0.0627(11) 0.0056(7) 0.0240(8) 0.0149(8) O2 0.0648(10) 0.0496(9) 0.0533(10) 0.0054(7) 0.0277(8) 0.0016(7) O3 0.0745(11) 0.0482(9) 0.0640(11) -0.0176(8) 0.0113(9) 0.0053(9) O4 0.0645(10) 0.0603(10) 0.0520(10) -0.0165(8) 0.0009(8) -0.0057(8) O5 0.0861(12) 0.0569(10) 0.0495(10) 0.0043(8) 0.0110(9) 0.0064(8) O6 0.1233(17) 0.0567(11) 0.0763(14) -0.0250(10) 0.0357(12) -0.0118(10) O7 0.0863(12) 0.0633(11) 0.0497(11) 0.0081(9) 0.0093(9) -0.0136(9) C2 0.0406(11) 0.0356(10) 0.0417(12) -0.0003(8) 0.0104(9) 0.0006(9) C3 0.0429(11) 0.0374(11) 0.0384(12) -0.0001(8) 0.0106(9) 0.0025(9) C4 0.0456(12) 0.0371(11) 0.0438(13) -0.0015(8) 0.0131(9) 0.0003(9) C5 0.0505(12) 0.0372(11) 0.0418(12) 0.0025(9) 0.0131(10) 0.0036(9) C6 0.0425(11) 0.0418(12) 0.0402(12) 0.0015(9) 0.0066(9) 0.0012(10) C7 0.0804(18) 0.0894(19) 0.0637(18) 0.0056(14) 0.0409(15) 0.0081(15) C8 0.142(2) 0.132(2) 0.129(2) 0.0343(16) 0.0808(17) -0.0039(16) C9 0.0423(12) 0.0439(12) 0.0519(15) -0.0020(9) 0.0152(10) -0.0022(11) C10 0.087(2) 0.0787(19) 0.072(2) -0.0357(16) 0.0045(16) -0.0169(16) C11 0.141(3) 0.072(2) 0.085(2) -0.012(2) 0.019(2) -0.0180(18) C12 0.0449(12) 0.0424(11) 0.0368(12) 0.0007(9) 0.0094(9) 0.0013(9) C13 0.0479(13) 0.0519(13) 0.0731(18) -0.0032(10) 0.0171(12) -0.0031(12) C14 0.0472(14) 0.0823(19) 0.085(2) -0.0060(13) 0.0218(13) -0.0096(16) C15 0.0543(15) 0.085(2) 0.0671(18) 0.0218(13) 0.0154(13) -0.0022(15) C16 0.0718(17) 0.0548(15) 0.0766(19) 0.0199(13) 0.0201(14) 0.0073(13) C17 0.0546(14) 0.0469(13) 0.0642(16) 0.0049(10) 0.0171(12) 0.0077(11) C18 0.0439(12) 0.0464(12) 0.0471(13) 0.0020(9) 0.0087(10) -0.0010(11) C19 0.0553(14) 0.0530(14) 0.0491(15) 0.0012(11) 0.0056(11) -0.0052(12) C20 0.131(3) 0.0688(18) 0.072(2) 0.0200(17) 0.0035(19) -0.0275(16) C21 0.0476(12) 0.0470(13) 0.0442(13) 0.0067(9) 0.0072(10) -0.0009(10) C22 0.0812(18) 0.0505(14) 0.0649(17) 0.0158(12) 0.0183(14) -0.0015(12) C23 0.102(2) 0.0648(18) 0.080(2) 0.0265(16) 0.0218(18) -0.0160(16) C24 0.083(2) 0.103(2) 0.077(2) 0.0192(18) 0.0290(17) -0.025(2) C25 0.0768(19) 0.100(2) 0.0669(19) -0.0079(16) 0.0358(15) -0.0105(17) C26 0.0670(16) 0.0576(15) 0.0631(17) -0.0018(12) 0.0236(13) -0.0036(13) 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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C2 N1 C5 110.00(16) C2 N1 H1N 112.7(15) C5 N1 H1N 112.8(14) C6 O2 C7 116.37(18) C9 O4 C10 116.42(19) C19 O7 C20 115.8(2) N1 C2 C9 106.88(16) N1 C2 C6 113.85(16) C9 C2 C6 111.21(17) N1 C2 C3 101.17(16) C9 C2 C3 113.06(16) C6 C2 C3 110.31(15) C12 C3 C4 117.24(16) C12 C3 C2 115.56(17) C4 C3 C2 102.13(15) C12 C3 H3 107.1 C4 C3 H3 107.1 C2 C3 H3 107.1 C18 C4 C3 113.50(17) C18 C4 C5 112.60(17) C3 C4 C5 106.19(15) C18 C4 H4 108.1 C3 C4 H4 108.1 C5 C4 H4 108.1 N1 C5 C21 111.04(17) N1 C5 C4 102.72(15) C21 C5 C4 116.51(17) N1 C5 H5 108.8 C21 C5 H5 108.8 C4 C5 H5 108.8 O1 C6 O2 124.6(2) O1 C6 C2 123.36(19) O2 C6 C2 111.96(17) C8 C7 O2 107.7(2) C8 C7 H7A 110.2 O2 C7 H7A 110.2 C8 C7 H7B 110.2 O2 C7 H7B 110.2 H7A C7 H7B 108.5 C7 C8 H8A 109.5 C7 C8 H8B 109.5 H8A C8 H8B 109.5 C7 C8 H8C 109.5 H8A C8 H8C 109.5 H8B C8 H8C 109.5 O3 C9 O4 124.67(19) O3 C9 C2 124.7(2) O4 C9 C2 110.54(18) O4 C10 C11 110.4(2) O4 C10 H10A 109.6 C11 C10 H10A 109.6 O4 C10 H10B 109.6 C11 C10 H10B 109.6 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 C17 117.3(2) C13 C12 C3 123.52(18) C17 C12 C3 119.14(18) C12 C13 C14 121.0(2) C12 C13 H13 119.5 C14 C13 H13 119.5 C15 C14 C13 120.6(2) C15 C14 H14 119.7 C13 C14 H14 119.7 C16 C15 C14 119.4(2) C16 C15 H15 120.3 C14 C15 H15 120.3 C15 C16 C17 120.4(2) C15 C16 H16 119.8 C17 C16 H16 119.8 C16 C17 C12 121.4(2) C16 C17 H17 119.3 C12 C17 H17 119.3 O5 C18 C4 125.16(19) O5 C18 C19 120.7(2) C4 C18 C19 114.14(19) O6 C19 O7 125.5(2) O6 C19 C18 122.4(2) O7 C19 C18 112.1(2) O7 C20 H20A 109.5 O7 C20 H20B 109.5 H20A C20 H20B 109.5 O7 C20 H20C 109.5 H20A C20 H20C 109.5 H20B C20 H20C 109.5 C22 C21 C26 118.0(2) C22 C21 C5 120.3(2) C26 C21 C5 121.66(19) C21 C22 C23 121.0(3) C21 C22 H22 119.5 C23 C22 H22 119.5 C24 C23 C22 119.7(3) C24 C23 H23 120.1 C22 C23 H23 120.1 C25 C24 C23 120.5(3) C25 C24 H24 119.7 C23 C24 H24 119.7 C24 C25 C26 120.0(3) C24 C25 H25 120.0 C26 C25 H25 120.0 C21 C26 C25 120.7(2) C21 C26 H26 119.6 C25 C26 H26 119.6 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance N1 C2 1.453(2) N1 C5 1.472(3) N1 H1N 0.878(16) O1 C6 1.203(2) O2 C6 1.318(2) O2 C7 1.457(3) O3 C9 1.196(3) O4 C9 1.330(3) O4 C10 1.455(3) O5 C18 1.198(3) O6 C19 1.187(3) O7 C19 1.317(3) O7 C20 1.449(3) C2 C9 1.527(3) C2 C6 1.536(3) C2 C3 1.551(3) C3 C12 1.520(3) C3 C4 1.533(3) C3 H3 0.9800 C4 C18 1.507(3) C4 C5 1.569(3) C4 H4 0.9800 C5 C21 1.513(3) C5 H5 0.9800 C7 C8 1.453(4) C7 H7A 0.9700 C7 H7B 0.9700 C8 H8A 0.9600 C8 H8B 0.9600 C8 H8C 0.9600 C10 C11 1.489(4) C10 H10A 0.9700 C10 H10B 0.9700 C11 H11A 0.9600 C11 H11B 0.9600 C11 H11C 0.9600 C12 C13 1.381(3) C12 C17 1.383(3) C13 C14 1.382(3) C13 H13 0.9300 C14 C15 1.362(4) C14 H14 0.9300 C15 C16 1.362(4) C15 H15 0.9300 C16 C17 1.378(3) C16 H16 0.9300 C17 H17 0.9300 C18 C19 1.533(3) C20 H20A 0.9600 C20 H20B 0.9600 C20 H20C 0.9600 C21 C22 1.379(3) C21 C26 1.382(3) C22 C23 1.388(4) C22 H22 0.9300 C23 C24 1.364(4) C23 H23 0.9300 C24 C25 1.355(4) C24 H24 0.9300 C25 C26 1.392(4) C25 H25 0.9300 C26 H26 0.9300 loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA N1 H1N O1 3_757 0.878(16) 2.269(18) 3.061(2) 150(2) C23 H23 O3 2_746 0.93 2.54 3.461(3) 169.6 C25 H25 O7 3_756 0.93 2.60 3.526(3) 172.2 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 C5 N1 C2 C9 -159.71(17) C5 N1 C2 C6 77.1(2) C5 N1 C2 C3 -41.2(2) N1 C2 C3 C12 168.35(16) C9 C2 C3 C12 -77.7(2) C6 C2 C3 C12 47.5(2) N1 C2 C3 C4 39.90(18) C9 C2 C3 C4 153.85(16) C6 C2 C3 C4 -80.93(19) C12 C3 C4 C18 82.3(2) C2 C3 C4 C18 -150.29(17) C12 C3 C4 C5 -153.43(17) C2 C3 C4 C5 -26.1(2) C2 N1 C5 C21 149.70(17) C2 N1 C5 C4 24.5(2) C18 C4 C5 N1 127.43(18) C3 C4 C5 N1 2.6(2) C18 C4 C5 C21 5.8(2) C3 C4 C5 C21 -118.94(19) C7 O2 C6 O1 -3.3(3) C7 O2 C6 C2 173.36(18) N1 C2 C6 O1 -19.7(3) C9 C2 C6 O1 -140.5(2) C3 C2 C6 O1 93.2(2) N1 C2 C6 O2 163.56(16) C9 C2 C6 O2 42.8(2) C3 C2 C6 O2 -83.5(2) C6 O2 C7 C8 -171.9(3) C10 O4 C9 O3 8.3(3) C10 O4 C9 C2 -175.66(19) N1 C2 C9 O3 96.2(2) C6 C2 C9 O3 -139.0(2) C3 C2 C9 O3 -14.3(3) N1 C2 C9 O4 -79.9(2) C6 C2 C9 O4 45.0(2) C3 C2 C9 O4 169.70(17) C9 O4 C10 C11 84.5(3) C4 C3 C12 C13 28.5(3) C2 C3 C12 C13 -92.0(2) C4 C3 C12 C17 -154.38(19) C2 C3 C12 C17 85.1(2) C17 C12 C13 C14 -1.5(4) C3 C12 C13 C14 175.6(2) C12 C13 C14 C15 0.3(4) C13 C14 C15 C16 0.6(4) C14 C15 C16 C17 -0.3(4) C15 C16 C17 C12 -1.0(4) C13 C12 C17 C16 1.9(4) C3 C12 C17 C16 -175.4(2) C3 C4 C18 O5 9.5(3) C5 C4 C18 O5 -111.1(2) C3 C4 C18 C19 -169.00(17) C5 C4 C18 C19 70.3(2) C20 O7 C19 O6 -0.1(4) C20 O7 C19 C18 -179.9(2) O5 C18 C19 O6 -153.7(2) C4 C18 C19 O6 24.9(3) O5 C18 C19 O7 26.1(3) C4 C18 C19 O7 -155.34(19) N1 C5 C21 C22 133.7(2) C4 C5 C21 C22 -109.2(2) N1 C5 C21 C26 -46.4(3) C4 C5 C21 C26 70.7(3) C26 C21 C22 C23 0.5(4) C5 C21 C22 C23 -179.6(2) C21 C22 C23 C24 0.1(4) C22 C23 C24 C25 -0.8(5) C23 C24 C25 C26 0.8(5) C22 C21 C26 C25 -0.5(4) C5 C21 C26 C25 179.6(2) C24 C25 C26 C21 -0.1(4)