#------------------------------------------------------------------------------ #$Date: 2014-07-12 07:06:18 +0300 (Sat, 12 Jul 2014) $ #$Revision: 120112 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/20/47/7204795.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_7204795 loop_ _publ_author_name 'Christer B. Aaker\"oy' 'John Desper' 'Brian A. Helfrich' _publ_section_title ; Heteromeric intermolecular interactions as synthetic tools for the formation of binary co-crystals ; _journal_issue 5 _journal_name_full CrystEngComm _journal_page_first 19 _journal_page_last 24 _journal_volume 6 _journal_year 2004 _chemical_formula_moiety ; (C15 H15 N3 O2) (C7 H4 N2 O6) ; _chemical_formula_sum 'C22 H19 N5 O8' _chemical_formula_weight 481.42 _chemical_name_common ;2-(4-(dimethylamino)phenylazo)benzoic acid, 3,5- dinitrobenzoic acid ; _chemical_name_systematic ; 2-[4-(dimethylamino)phenylazo]benzoic acid, 3,5-dinitrobenzoic acid ; _chemical_temperature_decomposition 149.0(10) _space_group_IT_number 2 _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 101.186(2) _cell_angle_beta 97.114(2) _cell_angle_gamma 101.401(2) _cell_formula_units_Z 2 _cell_length_a 7.0051(5) _cell_length_b 8.6187(7) _cell_length_c 18.5866(15) _cell_measurement_reflns_used 2368 _cell_measurement_temperature 203(2) _cell_measurement_theta_max 27.2 _cell_measurement_theta_min 2.50 _cell_volume 1063.66(14) _computing_cell_refinement 'Bruker SMART' _computing_data_collection 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _diffrn_ambient_temperature 203(2) _diffrn_measured_fraction_theta_full 0.907 _diffrn_measured_fraction_theta_max 0.907 _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0508 _diffrn_reflns_av_sigmaI/netI 0.0669 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_number 8137 _diffrn_reflns_theta_full 28.21 _diffrn_reflns_theta_max 28.21 _diffrn_reflns_theta_min 2.27 _exptl_absorpt_coefficient_mu 0.117 _exptl_absorpt_correction_type none _exptl_crystal_colour red _exptl_crystal_density_diffrn 1.503 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 500 _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _refine_diff_density_max 0.271 _refine_diff_density_min -0.215 _refine_diff_density_rms 0.064 _refine_ls_extinction_coef 0.064(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL _refine_ls_goodness_of_fit_ref 0.891 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 323 _refine_ls_number_reflns 4765 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.891 _refine_ls_R_factor_all 0.0835 _refine_ls_R_factor_gt 0.0471 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0700P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1117 _refine_ls_wR_factor_ref 0.1278 _reflns_number_gt 2692 _reflns_number_total 4765 _reflns_threshold_expression >2sigma(I) _[local]_cod_data_source_file b315181f.txt _[local]_cod_data_source_block 1 _[local]_cod_cif_authors_sg_H-M P-1 _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic' according to '/home/adriana/struct/CIF-dictionaries/cif_core.dic' dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_enum 1555 2011-01-17 13:19:09Z saulius The following automatic conversions were performed: '_chemical_melting_point' tag was changed to '_chemical_temperature_decomposition' since the value had been given as '148-150 (dec)'. The value was changed to '149.0(10)' - the average value was taken and precision was estimated. Automatic conversion script Id: cif_fix_values 1569 2011-02-09 13:29:24Z adriana ; _cod_database_code 7204795 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' 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 0.2478(2) 0.3052(2) 0.61067(9) 0.0328(4) Uani 1 1 d . . . C2 C 0.3005(3) 0.3538(2) 0.68838(10) 0.0354(4) Uani 1 1 d . . . C3 C 0.2852(3) 0.2340(2) 0.72942(10) 0.0403(5) Uani 1 1 d . . . H3 H 0.3199 0.2647 0.7815 0.048 Uiso 1 1 calc R . . C4 C 0.2208(3) 0.0723(3) 0.69554(11) 0.0433(5) Uani 1 1 d . . . H4 H 0.2117 -0.0067 0.7242 0.052 Uiso 1 1 calc R . . C5 C 0.1692(3) 0.0262(2) 0.61860(11) 0.0408(5) Uani 1 1 d . . . H5 H 0.1242 -0.0843 0.5951 0.049 Uiso 1 1 calc R . . C6 C 0.1836(3) 0.1410(2) 0.57680(10) 0.0359(4) Uani 1 1 d . . . H6 H 0.1498 0.1086 0.5247 0.043 Uiso 1 1 calc R . . O7 O 0.4225(2) 0.56045(18) 0.79677(8) 0.0620(4) Uani 1 1 d . . . C7 C 0.3734(3) 0.5257(3) 0.72907(11) 0.0440(5) Uani 1 1 d . . . O8 O 0.3850(2) 0.64019(17) 0.69175(8) 0.0541(4) Uani 1 1 d . . . H8 H 0.344(3) 0.582(3) 0.6375(13) 0.065 Uiso 1 1 d . . . N9 N 0.2639(2) 0.42995(18) 0.57033(8) 0.0325(3) Uani 1 1 d . . . N10 N 0.2174(2) 0.38124(18) 0.49998(8) 0.0355(4) Uani 1 1 d . . . C11 C 0.2315(3) 0.5005(2) 0.45928(10) 0.0337(4) Uani 1 1 d . . . C12 C 0.1799(3) 0.4452(2) 0.38238(10) 0.0381(4) Uani 1 1 d . . . H12 H 0.1386 0.3329 0.3620 0.046 Uiso 1 1 calc R . . C13 C 0.1879(3) 0.5502(2) 0.33601(10) 0.0401(5) Uani 1 1 d . . . H13 H 0.1527 0.5090 0.2843 0.048 Uiso 1 1 calc R . . C14 C 0.2479(2) 0.7191(2) 0.36414(10) 0.0341(4) Uani 1 1 d . . . C15 C 0.2991(3) 0.7747(2) 0.44252(10) 0.0386(4) Uani 1 1 d . . . H15 H 0.3391 0.8868 0.4634 0.046 Uiso 1 1 calc R . . C16 C 0.2913(3) 0.6677(2) 0.48821(10) 0.0365(4) Uani 1 1 d . . . H16 H 0.3269 0.7075 0.5400 0.044 Uiso 1 1 calc R . . N17 N 0.2558(2) 0.82228(19) 0.31752(9) 0.0408(4) Uani 1 1 d . . . C18 C 0.2041(3) 0.7603(3) 0.23747(11) 0.0502(5) Uani 1 1 d . . . H18A H 0.2873 0.6873 0.2213 0.075 Uiso 1 1 calc R . . H18B H 0.2239 0.8502 0.2128 0.075 Uiso 1 1 calc R . . H18C H 0.0667 0.7022 0.2249 0.075 Uiso 1 1 calc R . . C19 C 0.3171(3) 0.9977(2) 0.34458(13) 0.0546(6) Uani 1 1 d . . . H19A H 0.2282 1.0343 0.3767 0.082 Uiso 1 1 calc R . . H19B H 0.3135 1.0496 0.3027 0.082 Uiso 1 1 calc R . . H19C H 0.4505 1.0262 0.3724 0.082 Uiso 1 1 calc R . . C21 C 0.6894(3) 1.0914(2) 0.95849(9) 0.0336(4) Uani 1 1 d . . . C22 C 0.6803(3) 1.2506(2) 0.96045(10) 0.0379(4) Uani 1 1 d . . . H22 H 0.6137 1.2785 0.9194 0.045 Uiso 1 1 calc R . . N23 N 0.7626(3) 1.5386(2) 1.02524(12) 0.0560(5) Uani 1 1 d . . . C23 C 0.7701(3) 1.3682(2) 1.02340(11) 0.0393(5) Uani 1 1 d . . . O23 O 0.6839(3) 1.5685(2) 0.96900(11) 0.0821(6) Uani 1 1 d . . . O24 O 0.8353(3) 1.63903(19) 1.08151(11) 0.0872(6) Uani 1 1 d . . . C24 C 0.8664(3) 1.3332(2) 1.08520(10) 0.0381(4) Uani 1 1 d . . . H24 H 0.9256 1.4147 1.1279 0.046 Uiso 1 1 calc R . . O25 O 1.0259(2) 1.23669(18) 1.20393(8) 0.0656(5) Uani 1 1 d . . . N25 N 0.9685(2) 1.1311(2) 1.14751(9) 0.0420(4) Uani 1 1 d . . . C25 C 0.8722(3) 1.1737(2) 1.08165(10) 0.0336(4) Uani 1 1 d . . . O26 O 0.9858(2) 0.99167(17) 1.14194(7) 0.0502(4) Uani 1 1 d . . . C26 C 0.7876(2) 1.0520(2) 1.01960(9) 0.0323(4) Uani 1 1 d . . . H26 H 0.7962 0.9442 1.0186 0.039 Uiso 1 1 calc R . . O27 O 0.4774(2) 0.99457(17) 0.84181(7) 0.0521(4) Uani 1 1 d . . . C27 C 0.5846(3) 0.9650(2) 0.89078(10) 0.0378(4) Uani 1 1 d . . . O28 O 0.6192(2) 0.82275(17) 0.89296(7) 0.0475(4) Uani 1 1 d . . . H28 H 0.566(3) 0.752(3) 0.8570(12) 0.057 Uiso 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 0.0278(9) 0.0376(11) 0.0322(10) 0.0075(8) 0.0026(7) 0.0072(8) C2 0.0305(9) 0.0420(11) 0.0314(10) 0.0058(8) 0.0022(7) 0.0072(8) C3 0.0380(11) 0.0520(13) 0.0313(10) 0.0118(9) 0.0048(8) 0.0095(9) C4 0.0422(11) 0.0479(13) 0.0436(12) 0.0200(10) 0.0068(9) 0.0095(9) C5 0.0419(11) 0.0355(11) 0.0443(12) 0.0106(9) 0.0052(9) 0.0068(9) C6 0.0363(10) 0.0379(11) 0.0305(10) 0.0065(8) 0.0005(8) 0.0060(8) O7 0.0818(11) 0.0564(10) 0.0324(8) -0.0005(7) -0.0029(7) -0.0021(8) C7 0.0435(11) 0.0450(12) 0.0366(11) 0.0024(9) 0.0030(9) 0.0030(9) O8 0.0742(10) 0.0398(9) 0.0379(8) 0.0001(7) 0.0016(7) 0.0022(7) N9 0.0334(8) 0.0337(9) 0.0286(8) 0.0049(7) 0.0024(6) 0.0070(7) N10 0.0381(9) 0.0350(9) 0.0311(8) 0.0063(7) 0.0026(6) 0.0062(7) C11 0.0355(10) 0.0321(10) 0.0329(10) 0.0067(8) 0.0039(8) 0.0080(8) C12 0.0470(11) 0.0292(10) 0.0346(10) 0.0038(8) 0.0025(8) 0.0067(8) C13 0.0491(12) 0.0372(11) 0.0327(10) 0.0076(8) 0.0041(8) 0.0085(9) C14 0.0289(9) 0.0375(11) 0.0393(10) 0.0133(8) 0.0075(8) 0.0095(8) C15 0.0404(11) 0.0296(10) 0.0417(11) 0.0035(9) 0.0033(8) 0.0050(8) C16 0.0394(10) 0.0348(11) 0.0318(10) 0.0030(8) 0.0025(8) 0.0069(8) N17 0.0452(9) 0.0365(9) 0.0442(10) 0.0174(8) 0.0079(7) 0.0090(7) C18 0.0569(13) 0.0576(14) 0.0427(12) 0.0247(10) 0.0083(10) 0.0152(11) C19 0.0563(13) 0.0382(12) 0.0727(15) 0.0211(11) 0.0140(11) 0.0087(10) C21 0.0362(10) 0.0354(10) 0.0308(9) 0.0112(8) 0.0076(8) 0.0070(8) C22 0.0404(11) 0.0412(12) 0.0365(10) 0.0181(9) 0.0077(8) 0.0099(9) N23 0.0645(13) 0.0360(11) 0.0749(14) 0.0236(11) 0.0157(11) 0.0153(10) C23 0.0440(11) 0.0286(10) 0.0499(12) 0.0147(9) 0.0128(9) 0.0105(8) O23 0.1089(15) 0.0541(11) 0.0957(14) 0.0436(10) 0.0045(11) 0.0294(10) O24 0.1268(17) 0.0282(9) 0.0932(14) 0.0014(9) -0.0053(12) 0.0129(10) C24 0.0436(11) 0.0310(10) 0.0371(10) 0.0043(8) 0.0070(8) 0.0055(8) O25 0.0956(13) 0.0498(10) 0.0382(8) -0.0038(7) -0.0161(8) 0.0163(9) N25 0.0495(10) 0.0376(10) 0.0348(9) 0.0059(8) -0.0012(7) 0.0074(8) C25 0.0369(10) 0.0316(10) 0.0320(10) 0.0081(8) 0.0032(8) 0.0073(8) O26 0.0658(10) 0.0375(8) 0.0466(8) 0.0132(7) -0.0041(7) 0.0149(7) C26 0.0360(10) 0.0284(10) 0.0348(10) 0.0096(8) 0.0082(8) 0.0086(8) O27 0.0594(9) 0.0568(10) 0.0369(8) 0.0151(7) -0.0053(7) 0.0096(7) C27 0.0429(11) 0.0400(11) 0.0320(10) 0.0140(9) 0.0082(8) 0.0058(9) O28 0.0643(10) 0.0338(8) 0.0359(8) 0.0027(6) -0.0051(7) 0.0049(7) 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 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 C1 C2 119.80(17) . . ? C6 C1 N9 123.18(16) . . ? C2 C1 N9 117.02(16) . . ? C3 C2 C1 118.26(17) . . ? C3 C2 C7 118.26(17) . . ? C1 C2 C7 123.47(17) . . ? C4 C3 C2 121.52(18) . . ? C4 C3 H3 119.2 . . ? C2 C3 H3 119.2 . . ? C3 C4 C5 119.51(18) . . ? C3 C4 H4 120.2 . . ? C5 C4 H4 120.2 . . ? C6 C5 C4 120.30(19) . . ? C6 C5 H5 119.8 . . ? C4 C5 H5 119.8 . . ? C5 C6 C1 120.59(17) . . ? C5 C6 H6 119.7 . . ? C1 C6 H6 119.7 . . ? O7 C7 O8 120.22(19) . . ? O7 C7 C2 120.55(19) . . ? O8 C7 C2 119.23(17) . . ? C7 O8 H8 105.5(13) . . ? N10 N9 C1 115.24(15) . . ? N9 N10 C11 116.44(15) . . ? N10 C11 C12 115.73(16) . . ? N10 C11 C16 126.13(16) . . ? C12 C11 C16 118.14(17) . . ? C13 C12 C11 121.52(18) . . ? C13 C12 H12 119.2 . . ? C11 C12 H12 119.2 . . ? C12 C13 C14 121.14(18) . . ? C12 C13 H13 119.4 . . ? C14 C13 H13 119.4 . . ? N17 C14 C13 120.63(17) . . ? N17 C14 C15 122.28(17) . . ? C13 C14 C15 117.09(17) . . ? C16 C15 C14 121.03(18) . . ? C16 C15 H15 119.5 . . ? C14 C15 H15 119.5 . . ? C15 C16 C11 121.08(17) . . ? C15 C16 H16 119.5 . . ? C11 C16 H16 119.5 . . ? C14 N17 C18 120.60(16) . . ? C14 N17 C19 122.19(17) . . ? C18 N17 C19 117.21(16) . . ? N17 C18 H18A 109.5 . . ? N17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? N17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? N17 C19 H19A 109.5 . . ? N17 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? N17 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C22 C21 C26 119.85(17) . . ? C22 C21 C27 118.16(17) . . ? C26 C21 C27 121.94(17) . . ? C23 C22 C21 119.05(18) . . ? C23 C22 H22 120.5 . . ? C21 C22 H22 120.5 . . ? O24 N23 O23 124.2(2) . . ? O24 N23 C23 118.4(2) . . ? O23 N23 C23 117.4(2) . . ? C24 C23 C22 122.61(18) . . ? C24 C23 N23 118.28(19) . . ? C22 C23 N23 119.11(19) . . ? C25 C24 C23 116.94(18) . . ? C25 C24 H24 121.5 . . ? C23 C24 H24 121.5 . . ? O25 N25 O26 124.11(17) . . ? O25 N25 C25 118.10(17) . . ? O26 N25 C25 117.79(16) . . ? C24 C25 C26 122.70(17) . . ? C24 C25 N25 118.40(17) . . ? C26 C25 N25 118.89(16) . . ? C25 C26 C21 118.84(17) . . ? C25 C26 H26 120.6 . . ? C21 C26 H26 120.6 . . ? O27 C27 O28 125.55(19) . . ? O27 C27 C21 122.34(18) . . ? O28 C27 C21 112.08(17) . . ? C27 O28 H28 114.9(16) . . ? 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 C6 1.391(2) . ? C1 C2 1.404(2) . ? C1 N9 1.420(2) . ? C2 C3 1.393(3) . ? C2 C7 1.483(3) . ? C3 C4 1.372(3) . ? C3 H3 0.9400 . ? C4 C5 1.389(3) . ? C4 H4 0.9400 . ? C5 C6 1.368(3) . ? C5 H5 0.9400 . ? C6 H6 0.9400 . ? O7 C7 1.224(2) . ? C7 O8 1.307(2) . ? O8 H8 1.01(2) . ? N9 N10 1.2726(19) . ? N10 C11 1.385(2) . ? C11 C12 1.393(2) . ? C11 C16 1.396(2) . ? C12 C13 1.364(3) . ? C12 H12 0.9400 . ? C13 C14 1.406(3) . ? C13 H13 0.9400 . ? C14 N17 1.355(2) . ? C14 C15 1.419(2) . ? C15 C16 1.367(3) . ? C15 H15 0.9400 . ? C16 H16 0.9400 . ? N17 C18 1.453(2) . ? N17 C19 1.455(2) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C18 H18C 0.9700 . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C19 H19C 0.9700 . ? C21 C22 1.380(2) . ? C21 C26 1.388(2) . ? C21 C27 1.494(3) . ? C22 C23 1.377(3) . ? C22 H22 0.9400 . ? N23 O24 1.202(2) . ? N23 O23 1.217(2) . ? N23 C23 1.474(2) . ? C23 C24 1.374(3) . ? C24 C25 1.372(2) . ? C24 H24 0.9400 . ? O25 N25 1.2125(19) . ? N25 O26 1.2172(19) . ? N25 C25 1.468(2) . ? C25 C26 1.377(2) . ? C26 H26 0.9400 . ? O27 C27 1.206(2) . ? C27 O28 1.303(2) . ? O28 H28 0.81(2) . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O28 H28 O7 0.81(2) 1.82(2) 2.6069(19) 163(2) . O8 H8 N9 1.01(2) 1.58(2) 2.5353(19) 156(2) . C13 H13 O25 0.94 2.45 3.184(2) 134.6 1_444 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 -0.4(2) . . . . ? N9 C1 C2 C3 179.70(15) . . . . ? C6 C1 C2 C7 179.01(16) . . . . ? N9 C1 C2 C7 -0.9(2) . . . . ? C1 C2 C3 C4 0.1(3) . . . . ? C7 C2 C3 C4 -179.36(16) . . . . ? C2 C3 C4 C5 -0.1(3) . . . . ? C3 C4 C5 C6 0.4(3) . . . . ? C4 C5 C6 C1 -0.7(3) . . . . ? C2 C1 C6 C5 0.7(3) . . . . ? N9 C1 C6 C5 -179.37(16) . . . . ? C3 C2 C7 O7 1.5(3) . . . . ? C1 C2 C7 O7 -177.89(18) . . . . ? C3 C2 C7 O8 -178.63(18) . . . . ? C1 C2 C7 O8 2.0(3) . . . . ? C6 C1 N9 N10 -0.8(2) . . . . ? C2 C1 N9 N10 179.08(14) . . . . ? C1 N9 N10 C11 179.88(14) . . . . ? N9 N10 C11 C12 -179.93(15) . . . . ? N9 N10 C11 C16 0.0(3) . . . . ? N10 C11 C12 C13 -179.80(17) . . . . ? C16 C11 C12 C13 0.3(3) . . . . ? C11 C12 C13 C14 -0.3(3) . . . . ? C12 C13 C14 N17 179.81(18) . . . . ? C12 C13 C14 C15 -0.1(3) . . . . ? N17 C14 C15 C16 -179.45(17) . . . . ? C13 C14 C15 C16 0.5(3) . . . . ? C14 C15 C16 C11 -0.4(3) . . . . ? N10 C11 C16 C15 -179.83(17) . . . . ? C12 C11 C16 C15 0.1(3) . . . . ? C13 C14 N17 C18 -0.6(3) . . . . ? C15 C14 N17 C18 179.35(17) . . . . ? C13 C14 N17 C19 179.96(16) . . . . ? C15 C14 N17 C19 -0.1(3) . . . . ? C26 C21 C22 C23 0.2(3) . . . . ? C27 C21 C22 C23 177.78(15) . . . . ? C21 C22 C23 C24 -1.1(3) . . . . ? C21 C22 C23 N23 179.28(16) . . . . ? O24 N23 C23 C24 -2.4(3) . . . . ? O23 N23 C23 C24 177.04(19) . . . . ? O24 N23 C23 C22 177.29(19) . . . . ? O23 N23 C23 C22 -3.3(3) . . . . ? C22 C23 C24 C25 0.8(3) . . . . ? N23 C23 C24 C25 -179.56(16) . . . . ? C23 C24 C25 C26 0.3(3) . . . . ? C23 C24 C25 N25 -178.13(16) . . . . ? O25 N25 C25 C24 5.3(3) . . . . ? O26 N25 C25 C24 -174.65(16) . . . . ? O25 N25 C25 C26 -173.21(16) . . . . ? O26 N25 C25 C26 6.8(3) . . . . ? C24 C25 C26 C21 -1.1(3) . . . . ? N25 C25 C26 C21 177.33(15) . . . . ? C22 C21 C26 C25 0.8(2) . . . . ? C27 C21 C26 C25 -176.63(15) . . . . ? C22 C21 C27 O27 -7.6(3) . . . . ? C26 C21 C27 O27 169.89(17) . . . . ? C22 C21 C27 O28 174.18(16) . . . . ? C26 C21 C27 O28 -8.3(2) . . . . ? _journal_paper_doi 10.1039/b315181f