#------------------------------------------------------------------------------ #$Date: 2010-01-30 15:59:17 +0200 (Sat, 30 Jan 2010) $ #$Revision: 966 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/2207352.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_2207352 _space_group_IT_number 7 _symmetry_space_group_name_Hall 'P -2yc' _symmetry_space_group_name_H-M 'P 1 c 1' _[local]_cod_cif_authors_sg_H-M 'P c' loop_ _publ_author_name 'da Silva, Luiz Everson' 'Joussef, Antonio C.' 'Foro, Sabine' 'Schmidt, Boris' _publ_section_title ; N-Benzyl-8-nitroquinolin-2-amine ; _journal_coeditor_code SU6227 _journal_issue 11 _journal_name_full 'Acta Crystallographica, Section E' _journal_page_first o3837 _journal_page_last o3838 _journal_volume 61 _journal_year 2005 _chemical_formula_iupac 'C16 H13 N3 O2' _chemical_formula_moiety 'C16 H13 N3 O2' _chemical_formula_sum 'C16 H13 N3 O2' _chemical_formula_weight 279.29 _chemical_name_systematic ; N-Benzyl-8-nitroquinolin-2-amine ; _symmetry_cell_setting monoclinic _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 93.960(10) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 7.4390(10) _cell_length_b 11.2150(10) _cell_length_c 16.5410(10) _cell_measurement_reflns_used 25 _cell_measurement_temperature 299(2) _cell_measurement_theta_max 19.40 _cell_measurement_theta_min 3.94 _cell_volume 1376.7(2) _computing_cell_refinement ; CAD-4/PC Software ; _computing_data_collection ; CAD-4/PC Software (Nonius, 1996) ; _computing_data_reduction 'REDU4 (Stoe & Cie, 1987)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 299(2) _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device_type 'Nonius CAD-4' _diffrn_measurement_method \w/2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54180 _diffrn_reflns_av_R_equivalents 0.0144 _diffrn_reflns_av_sigmaI/netI 0.0187 _diffrn_reflns_limit_h_max 0 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 1 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_number 2913 _diffrn_reflns_theta_full 67.92 _diffrn_reflns_theta_max 67.92 _diffrn_reflns_theta_min 3.94 _diffrn_standards_decay_% 1.0 _diffrn_standards_interval_time 120 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.748 _exptl_absorpt_correction_type none _exptl_crystal_colour orange _exptl_crystal_density_diffrn 1.348 _exptl_crystal_density_method 'not measured' _exptl_crystal_description needle _exptl_crystal_F_000 584 _exptl_crystal_size_max 0.68 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _refine_diff_density_max 0.163 _refine_diff_density_min -0.203 _refine_ls_abs_structure_details 'none; Friedel pairs merged' _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.077 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 379 _refine_ls_number_reflns 2497 _refine_ls_number_restraints 2 _refine_ls_restrained_S_all 1.077 _refine_ls_R_factor_all 0.0530 _refine_ls_R_factor_gt 0.0459 _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^)+(0.0853P)^2^+0.028P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1132 _refine_ls_wR_factor_ref 0.1185 _reflns_number_gt 2233 _reflns_number_total 2497 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file su6227.cif loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0000 '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 0.0311 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _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_type_symbol O1 0.6479(4) 0.0074(2) 0.56618(15) 0.0832(8) Uani d . 1 O O2 0.7853(5) -0.1592(3) 0.55330(19) 0.0948(9) Uani d . 1 O N1 0.8025(3) 0.1310(2) 0.43538(14) 0.0483(5) Uani d . 1 N N2 0.9293(3) 0.3181(3) 0.43035(18) 0.0605(7) Uani d . 1 N H2N 0.9479 0.3789 0.4002 0.073 Uiso d R 1 H N3 0.7053(4) -0.0717(2) 0.52474(16) 0.0588(6) Uani d . 1 N C1 0.7217(3) 0.0378(3) 0.39533(16) 0.0462(6) Uani d . 1 C C2 0.8469(4) 0.2242(3) 0.39204(18) 0.0505(7) Uani d . 1 C C3 0.8129(4) 0.2303(3) 0.3059(2) 0.0604(8) Uani d . 1 C H3 0.8457 0.2976 0.2775 0.073 Uiso calc R 1 H C4 0.7332(4) 0.1377(3) 0.26650(19) 0.0620(8) Uani d . 1 C H4 0.7107 0.1407 0.2105 0.074 Uiso calc R 1 H C5 0.6829(4) 0.0351(3) 0.30994(17) 0.0529(7) Uani d . 1 C C6 0.6003(4) -0.0644(3) 0.2731(2) 0.0651(9) Uani d . 1 C H6 0.5757 -0.0644 0.2172 0.078 Uiso calc R 1 H C7 0.5544(5) -0.1619(3) 0.3166(2) 0.0661(8) Uani d . 1 C H7 0.4986 -0.2270 0.2907 0.079 Uiso calc R 1 H C8 0.5923(4) -0.1624(3) 0.4001(2) 0.0603(8) Uani d . 1 C H8 0.5636 -0.2287 0.4304 0.072 Uiso calc R 1 H C9 0.6720(4) -0.0653(3) 0.43729(18) 0.0504(6) Uani d . 1 C C10 0.9608(4) 0.3268(3) 0.5174(2) 0.0646(8) Uani d . 1 C H10A 1.0658 0.3764 0.5301 0.078 Uiso calc R 1 H H10B 0.9865 0.2480 0.5395 0.078 Uiso calc R 1 H C11 0.8005(4) 0.3792(3) 0.55762(18) 0.0563(7) Uani d . 1 C C12 0.7751(7) 0.5012(3) 0.5620(3) 0.0828(11) Uani d . 1 C H12 0.8612 0.5523 0.5430 0.099 Uiso calc R 1 H C13 0.6242(9) 0.5482(5) 0.5940(3) 0.1075(18) Uani d . 1 C H13 0.6086 0.6304 0.5963 0.129 Uiso calc R 1 H C14 0.4991(8) 0.4743(6) 0.6219(3) 0.1050(17) Uani d . 1 C H14 0.3967 0.5060 0.6430 0.126 Uiso calc R 1 H C15 0.5216(6) 0.3532(5) 0.6195(2) 0.0809(11) Uani d . 1 C H15 0.4355 0.3032 0.6395 0.097 Uiso calc R 1 H C16 0.6725(5) 0.3054(3) 0.58721(19) 0.0618(8) Uani d . 1 C H16 0.6874 0.2231 0.5855 0.074 Uiso calc R 1 H O3 0.1486(5) 0.2968(2) 0.13557(17) 0.0872(8) Uani d . 1 O O4 0.3004(6) 0.1769(4) 0.0676(2) 0.1184(12) Uani d . 1 O N4 0.2999(3) 0.2281(2) 0.29424(14) 0.0507(6) Uani d . 1 N N5 0.4277(4) 0.3376(3) 0.40077(18) 0.0663(7) Uani d . 1 N H5N 0.4694 0.3440 0.4502 0.080 Uiso d R 1 H N6 0.2144(4) 0.2006(3) 0.12596(18) 0.0671(7) Uani d . 1 N C17 0.2232(3) 0.1241(3) 0.26696(19) 0.0499(6) Uani d . 1 C C18 0.3450(4) 0.2359(3) 0.37237(19) 0.0549(7) Uani d . 1 C C19 0.3129(4) 0.1431(4) 0.4288(2) 0.0657(9) Uani d . 1 C H19 0.3458 0.1528 0.4836 0.079 Uiso calc R 1 H C20 0.2355(4) 0.0426(4) 0.4017(2) 0.0663(9) Uani d . 1 C H20 0.2132 -0.0181 0.4380 0.080 Uiso calc R 1 H C21 0.1865(4) 0.0272(3) 0.3178(2) 0.0598(8) Uani d . 1 C C22 0.1118(5) -0.0777(3) 0.2848(3) 0.0768(11) Uani d . 1 C H22 0.0852 -0.1396 0.3194 0.092 Uiso calc R 1 H C23 0.0767(6) -0.0923(4) 0.2038(3) 0.0828(11) Uani d . 1 C H23 0.0276 -0.1633 0.1834 0.099 Uiso calc R 1 H C24 0.1147(5) -0.0001(3) 0.1517(3) 0.0724(9) Uani d . 1 C H24 0.0936 -0.0093 0.0960 0.087 Uiso calc R 1 H C25 0.1841(4) 0.1053(3) 0.1832(2) 0.0567(7) Uani d . 1 C C26 0.4415(4) 0.4442(3) 0.3536(2) 0.0658(8) Uani d . 1 C H26A 0.4711 0.4229 0.2993 0.079 Uiso calc R 1 H H26B 0.5388 0.4931 0.3775 0.079 Uiso calc R 1 H C27 0.2689(4) 0.5159(3) 0.3488(2) 0.0547(7) Uani d . 1 C C28 0.2263(5) 0.5870(3) 0.4127(2) 0.0669(9) Uani d . 1 C H28 0.3081 0.5953 0.4575 0.080 Uiso calc R 1 H C29 0.0630(7) 0.6461(3) 0.4108(3) 0.0805(11) Uani d . 1 C H29 0.0359 0.6943 0.4540 0.097 Uiso calc R 1 H C30 -0.0576(7) 0.6340(3) 0.3463(3) 0.0839(12) Uani d . 1 C H30 -0.1672 0.6740 0.3457 0.101 Uiso calc R 1 H C31 -0.0202(5) 0.5637(4) 0.2819(3) 0.0747(10) Uani d . 1 C H31 -0.1038 0.5558 0.2378 0.090 Uiso calc R 1 H C32 0.1439(5) 0.5041(3) 0.2831(2) 0.0602(8) Uani d . 1 C H32 0.1700 0.4561 0.2396 0.072 Uiso calc R 1 H 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 O1 0.123(2) 0.0750(15) 0.0531(13) -0.0014(15) 0.0195(14) 0.0002(12) O2 0.117(2) 0.0860(18) 0.0783(18) 0.0235(18) -0.0164(17) 0.0178(15) N1 0.0330(11) 0.0640(14) 0.0488(12) 0.0063(10) 0.0094(9) 0.0059(11) N2 0.0479(14) 0.0699(16) 0.0655(15) -0.0020(12) 0.0175(12) 0.0104(13) N3 0.0659(17) 0.0584(15) 0.0517(14) -0.0065(13) 0.0005(12) 0.0047(12) C1 0.0317(13) 0.0605(16) 0.0472(14) 0.0124(11) 0.0089(11) 0.0014(12) C2 0.0308(13) 0.0645(18) 0.0578(16) 0.0076(12) 0.0143(11) 0.0083(14) C3 0.0430(16) 0.081(2) 0.0595(18) 0.0107(15) 0.0206(14) 0.0172(16) C4 0.0508(17) 0.092(2) 0.0441(15) 0.0162(17) 0.0102(13) 0.0079(16) C5 0.0352(14) 0.078(2) 0.0468(14) 0.0160(13) 0.0105(11) 0.0006(14) C6 0.0529(18) 0.091(2) 0.0516(17) 0.0201(17) 0.0028(13) -0.0132(17) C7 0.0566(18) 0.071(2) 0.070(2) 0.0100(16) -0.0005(15) -0.0149(17) C8 0.0573(19) 0.0599(17) 0.0637(19) 0.0103(15) 0.0033(14) -0.0051(14) C9 0.0406(14) 0.0586(16) 0.0526(15) 0.0109(12) 0.0070(12) -0.0017(12) C10 0.0443(17) 0.077(2) 0.072(2) -0.0063(15) -0.0015(14) 0.0044(17) C11 0.0547(16) 0.0664(17) 0.0471(15) -0.0025(14) -0.0022(12) 0.0017(13) C12 0.108(3) 0.065(2) 0.076(2) -0.003(2) 0.017(2) 0.0035(18) C13 0.155(5) 0.086(3) 0.084(3) 0.037(3) 0.027(3) -0.001(2) C14 0.115(4) 0.139(5) 0.063(2) 0.048(4) 0.021(2) -0.003(3) C15 0.068(2) 0.118(3) 0.058(2) 0.004(2) 0.0135(16) 0.002(2) C16 0.0587(18) 0.073(2) 0.0536(16) -0.0015(16) 0.0025(13) -0.0012(15) O3 0.123(2) 0.0691(15) 0.0680(15) 0.0051(16) -0.0037(15) 0.0073(13) O4 0.135(3) 0.136(3) 0.091(2) 0.024(3) 0.054(2) 0.022(2) N4 0.0319(11) 0.0672(15) 0.0533(13) 0.0110(10) 0.0047(10) 0.0053(11) N5 0.0482(15) 0.0868(19) 0.0623(16) 0.0112(14) -0.0082(12) -0.0016(14) N6 0.0672(18) 0.0761(19) 0.0576(15) 0.0016(15) 0.0019(13) 0.0001(14) C17 0.0294(13) 0.0602(16) 0.0605(16) 0.0130(12) 0.0068(11) 0.0065(13) C18 0.0326(14) 0.075(2) 0.0570(16) 0.0182(13) 0.0033(12) 0.0036(14) C19 0.0476(17) 0.095(3) 0.0547(17) 0.0268(18) 0.0067(13) 0.0130(17) C20 0.0506(17) 0.078(2) 0.073(2) 0.0183(16) 0.0175(15) 0.0277(18) C21 0.0369(15) 0.0675(19) 0.076(2) 0.0123(13) 0.0114(14) 0.0179(16) C22 0.057(2) 0.065(2) 0.110(3) 0.0013(17) 0.018(2) 0.018(2) C23 0.064(2) 0.072(2) 0.111(3) -0.0054(19) 0.001(2) -0.001(2) C24 0.061(2) 0.072(2) 0.084(2) 0.0044(17) -0.0035(18) -0.0066(18) C25 0.0414(15) 0.0633(17) 0.0661(18) 0.0105(13) 0.0077(13) 0.0053(14) C26 0.0383(16) 0.084(2) 0.076(2) -0.0065(16) 0.0044(13) -0.0047(19) C27 0.0516(16) 0.0555(16) 0.0575(16) -0.0101(13) 0.0066(12) 0.0024(13) C28 0.079(2) 0.0577(18) 0.0638(19) -0.0130(17) 0.0030(17) -0.0019(14) C29 0.108(3) 0.0545(18) 0.082(2) 0.008(2) 0.031(2) -0.0018(17) C30 0.081(3) 0.062(2) 0.110(3) 0.021(2) 0.020(2) 0.012(2) C31 0.065(2) 0.072(2) 0.085(2) 0.0080(18) -0.0098(18) 0.0122(19) C32 0.0598(18) 0.0660(18) 0.0555(16) 0.0010(15) 0.0076(13) 0.0019(14) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O1 N3 1.217(4) O2 N3 1.225(4) N1 C2 1.323(4) N1 C1 1.356(4) N2 C2 1.354(4) N2 C10 1.446(5) N2 H2N 0.8617 N3 C9 1.452(4) C1 C9 1.411(4) C1 C5 1.422(4) C2 C3 1.432(4) C3 C4 1.342(5) C3 H3 0.9300 C4 C5 1.420(5) C4 H4 0.9300 C5 C6 1.393(5) C6 C7 1.365(6) C6 H6 0.9300 C7 C8 1.390(5) C7 H7 0.9300 C8 C9 1.366(4) C8 H8 0.9300 C10 C11 1.522(5) C10 H10A 0.9700 C10 H10B 0.9700 C11 C16 1.377(5) C11 C12 1.385(5) C12 C13 1.378(7) C12 H12 0.9300 C13 C14 1.351(8) C13 H13 0.9300 C14 C15 1.369(7) C14 H14 0.9300 C15 C16 1.384(5) C15 H15 0.9300 C16 H16 0.9300 O3 N6 1.200(4) O4 N6 1.224(4) N4 C18 1.316(4) N4 C17 1.362(4) N5 C18 1.364(5) N5 C26 1.435(5) N5 H5N 0.8571 N6 C25 1.455(4) C17 C21 1.412(4) C17 C25 1.412(4) C18 C19 1.429(5) C19 C20 1.328(5) C19 H19 0.9300 C20 C21 1.422(5) C20 H20 0.9300 C21 C22 1.396(6) C22 C23 1.357(6) C22 H22 0.9300 C23 C24 1.387(6) C23 H23 0.9300 C24 C25 1.377(5) C24 H24 0.9300 C26 C27 1.512(5) C26 H26A 0.9700 C26 H26B 0.9700 C27 C28 1.379(5) C27 C32 1.388(5) C28 C29 1.382(6) C28 H28 0.9300 C29 C30 1.352(7) C29 H29 0.9300 C30 C31 1.370(6) C30 H30 0.9300 C31 C32 1.391(5) C31 H31 0.9300 C32 H32 0.9300 loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C2 N1 C1 117.6(2) C2 N2 C10 123.8(3) C2 N2 H2N 115.5 C10 N2 H2N 120.1 O1 N3 O2 123.2(3) O1 N3 C9 118.9(3) O2 N3 C9 117.9(3) N1 C1 C9 120.9(2) N1 C1 C5 123.7(3) C9 C1 C5 115.4(3) N1 C2 N2 118.9(3) N1 C2 C3 122.9(3) N2 C2 C3 118.2(3) C4 C3 C2 119.2(3) C4 C3 H3 120.4 C2 C3 H3 120.4 C3 C4 C5 120.3(3) C3 C4 H4 119.9 C5 C4 H4 119.9 C6 C5 C4 123.4(3) C6 C5 C1 120.3(3) C4 C5 C1 116.3(3) C7 C6 C5 122.0(3) C7 C6 H6 119.0 C5 C6 H6 119.0 C6 C7 C8 119.1(3) C6 C7 H7 120.5 C8 C7 H7 120.5 C9 C8 C7 119.8(3) C9 C8 H8 120.1 C7 C8 H8 120.1 C8 C9 C1 123.5(3) C8 C9 N3 116.6(3) C1 C9 N3 119.9(3) N2 C10 C11 112.5(3) N2 C10 H10A 109.1 C11 C10 H10A 109.1 N2 C10 H10B 109.1 C11 C10 H10B 109.1 H10A C10 H10B 107.8 C16 C11 C12 118.4(4) C16 C11 C10 120.4(3) C12 C11 C10 121.2(3) C13 C12 C11 121.1(4) C13 C12 H12 119.5 C11 C12 H12 119.5 C14 C13 C12 119.7(5) C14 C13 H13 120.2 C12 C13 H13 120.2 C13 C14 C15 120.6(5) C13 C14 H14 119.7 C15 C14 H14 119.7 C14 C15 C16 120.0(4) C14 C15 H15 120.0 C16 C15 H15 120.0 C11 C16 C15 120.2(4) C11 C16 H16 119.9 C15 C16 H16 119.9 C18 N4 C17 117.1(3) C18 N5 C26 123.9(3) C18 N5 H5N 121.5 C26 N5 H5N 114.5 O3 N6 O4 122.7(4) O3 N6 C25 119.4(3) O4 N6 C25 117.8(3) N4 C17 C21 123.8(3) N4 C17 C25 120.4(3) C21 C17 C25 115.7(3) N4 C18 N5 118.2(3) N4 C18 C19 123.4(3) N5 C18 C19 118.4(3) C20 C19 C18 119.1(3) C20 C19 H19 120.4 C18 C19 H19 120.4 C19 C20 C21 120.5(3) C19 C20 H20 119.7 C21 C20 H20 119.7 C22 C21 C17 120.3(4) C22 C21 C20 123.6(3) C17 C21 C20 116.1(3) C23 C22 C21 122.1(4) C23 C22 H22 118.9 C21 C22 H22 118.9 C22 C23 C24 119.3(4) C22 C23 H23 120.4 C24 C23 H23 120.4 C25 C24 C23 119.5(4) C25 C24 H24 120.2 C23 C24 H24 120.2 C24 C25 C17 123.0(3) C24 C25 N6 117.1(3) C17 C25 N6 119.9(3) N5 C26 C27 112.3(3) N5 C26 H26A 109.2 C27 C26 H26A 109.2 N5 C26 H26B 109.2 C27 C26 H26B 109.2 H26A C26 H26B 107.9 C28 C27 C32 118.6(3) C28 C27 C26 120.4(3) C32 C27 C26 120.8(3) C27 C28 C29 120.5(4) C27 C28 H28 119.7 C29 C28 H28 119.7 C30 C29 C28 120.3(4) C30 C29 H29 119.9 C28 C29 H29 119.9 C29 C30 C31 120.8(4) C29 C30 H30 119.6 C31 C30 H30 119.6 C30 C31 C32 119.4(4) C30 C31 H31 120.3 C32 C31 H31 120.3 C27 C32 C31 120.4(3) C27 C32 H32 119.8 C31 C32 H32 119.8 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 C2 N1 C1 C9 179.4(2) C2 N1 C1 C5 0.2(3) C1 N1 C2 N2 -179.4(2) C1 N1 C2 C3 0.1(4) C10 N2 C2 N1 -4.6(4) C10 N2 C2 C3 175.8(3) N1 C2 C3 C4 -0.3(4) N2 C2 C3 C4 179.3(3) C2 C3 C4 C5 0.1(4) C3 C4 C5 C6 -179.8(3) C3 C4 C5 C1 0.1(4) N1 C1 C5 C6 179.6(3) C9 C1 C5 C6 0.4(4) N1 C1 C5 C4 -0.3(4) C9 C1 C5 C4 -179.5(2) C4 C5 C6 C7 179.7(3) C1 C5 C6 C7 -0.2(4) C5 C6 C7 C8 -0.5(5) C6 C7 C8 C9 1.0(5) C7 C8 C9 C1 -0.8(4) C7 C8 C9 N3 179.2(3) N1 C1 C9 C8 -179.1(3) C5 C1 C9 C8 0.1(4) N1 C1 C9 N3 0.9(4) C5 C1 C9 N3 -179.9(2) O1 N3 C9 C8 -126.1(3) O2 N3 C9 C8 51.6(4) O1 N3 C9 C1 53.9(4) O2 N3 C9 C1 -128.4(3) C2 N2 C10 C11 -86.2(4) N2 C10 C11 C16 93.7(4) N2 C10 C11 C12 -83.2(4) C16 C11 C12 C13 -1.0(6) C10 C11 C12 C13 176.0(4) C11 C12 C13 C14 0.3(8) C12 C13 C14 C15 0.6(8) C13 C14 C15 C16 -0.8(7) C12 C11 C16 C15 0.8(5) C10 C11 C16 C15 -176.2(3) C14 C15 C16 C11 0.1(6) C18 N4 C17 C21 1.6(4) C18 N4 C17 C25 -175.0(2) C17 N4 C18 N5 177.8(2) C17 N4 C18 C19 -1.8(4) C26 N5 C18 N4 10.9(4) C26 N5 C18 C19 -169.5(3) N4 C18 C19 C20 0.8(4) N5 C18 C19 C20 -178.8(3) C18 C19 C20 C21 0.5(4) N4 C17 C21 C22 -178.3(3) C25 C17 C21 C22 -1.6(4) N4 C17 C21 C20 -0.4(4) C25 C17 C21 C20 176.4(3) C19 C20 C21 C22 177.2(3) C19 C20 C21 C17 -0.7(4) C17 C21 C22 C23 1.9(5) C20 C21 C22 C23 -175.9(3) C21 C22 C23 C24 -0.5(6) C22 C23 C24 C25 -1.3(6) C23 C24 C25 C17 1.6(5) C23 C24 C25 N6 -177.5(3) N4 C17 C25 C24 176.7(3) C21 C17 C25 C24 -0.1(4) N4 C17 C25 N6 -4.2(4) C21 C17 C25 N6 179.0(3) O3 N6 C25 C24 125.7(3) O4 N6 C25 C24 -51.1(5) O3 N6 C25 C17 -53.4(4) O4 N6 C25 C17 129.8(4) C18 N5 C26 C27 79.1(4) N5 C26 C27 C28 78.8(4) N5 C26 C27 C32 -96.0(4) C32 C27 C28 C29 -0.6(5) C26 C27 C28 C29 -175.5(3) C27 C28 C29 C30 0.5(6) C28 C29 C30 C31 -0.2(6) C29 C30 C31 C32 0.0(6) C28 C27 C32 C31 0.4(5) C26 C27 C32 C31 175.3(3) C30 C31 C32 C27 -0.1(5) _cod_database_code 2207352