#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:43:10 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301803 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/34/2203488.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_2203488 loop_ _publ_author_name 'Zou, Wuxin' 'Yu, Haitao' 'Meng, Jiben' _publ_section_title ; 4-(N,N-Di-4-tolylamino)benzaldehyde (3-pyridylcarbonyl)hydrazone monohydrate ; _journal_issue 4 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o671 _journal_page_last o673 _journal_paper_doi 10.1107/S1600536804006464 _journal_volume 60 _journal_year 2004 _chemical_formula_iupac 'C27 H24 N4 O, H2 O' _chemical_formula_moiety 'C27 H24 N4 O, H2 O' _chemical_formula_sum 'C27 H26 N4 O2' _chemical_formula_weight 438.52 _chemical_name_systematic ; 4-(N,N-Di-4-tolylamino)benzaldehyde (3-pyridylcarbonyl)hydrazone monohydrate ; _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 106.951(5) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 11.425(3) _cell_length_b 12.404(4) _cell_length_c 17.374(5) _cell_measurement_reflns_used 998 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 23.96 _cell_measurement_theta_min 2.48 _cell_volume 2355.2(12) _computing_cell_refinement 'SAINT (Bruker, 1998)' _computing_data_collection 'SMART (Bruker, 1998)' _computing_data_reduction SAINT _computing_molecular_graphics 'SHELXTL (Sheldrick, 1998)' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1998)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1990)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.996 _diffrn_measurement_device_type 'Bruker SMART CCD area-detector' _diffrn_measurement_method '\f and \w' _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 0.0367 _diffrn_reflns_av_sigmaI/netI 0.0465 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_number 13225 _diffrn_reflns_theta_full 26.41 _diffrn_reflns_theta_max 26.41 _diffrn_reflns_theta_min 1.86 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.080 _exptl_absorpt_correction_T_max 0.984 _exptl_absorpt_correction_T_min 0.978 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_crystal_colour green-yellow _exptl_crystal_density_diffrn 1.237 _exptl_crystal_density_meas ? _exptl_crystal_description prism _exptl_crystal_F_000 928 _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.20 _refine_diff_density_max 0.316 _refine_diff_density_min -0.222 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.013 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 300 _refine_ls_number_reflns 4823 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.013 _refine_ls_R_factor_all 0.0903 _refine_ls_R_factor_gt 0.0500 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0635P)^2^+0.4561P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1177 _refine_ls_wR_factor_ref 0.1381 _reflns_number_gt 3093 _reflns_number_total 4823 _reflns_threshold_expression I>2\s(I) _cod_data_source_file om6222.cif _cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' according to '/home/saulius/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 1527 2010-12-29 10:47:43Z saulius The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' according to /home/saulius/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_values 1715 2011-07-08 13:25:40Z adriana The following automatic conversions were performed: '_exptl_crystal_density_meas' value 'none' was changed to '?' - the value is perceived as not measured. Automatic conversion script Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas ; _cod_original_cell_volume 2355.3(12) _cod_original_sg_symbol_Hall -P2ybc _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 2203488 _cod_database_fobs_code 2203488 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_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 N1 0.6285(2) 0.6144(2) -0.00995(12) 0.0761(6) Uani d . 1 N N2 0.52986(14) 0.54021(13) 0.23010(9) 0.0461(4) Uani d . 1 N H2 0.5386 0.4736 0.2191 0.055 Uiso calc R 1 H N3 0.48156(14) 0.56772(13) 0.29193(9) 0.0448(4) Uani d . 1 N N4 0.19990(15) 0.54972(13) 0.56390(10) 0.0469(4) Uani d . 1 N O1 0.55038(14) 0.71553(11) 0.19883(9) 0.0608(4) Uani d . 1 O H2A 0.4301 0.3488 0.1414 0.091 Uiso d R 1 H H2B 0.4903 0.2704 0.1962 0.091 Uiso d R 1 H C1 0.5887(2) 0.63883(19) 0.05217(13) 0.0595(6) Uani d . 1 C H1 0.5389 0.6992 0.0476 0.071 Uiso calc R 1 H C2 0.61545(18) 0.58157(16) 0.12313(11) 0.0458(5) Uani d . 1 C C3 0.6906(2) 0.4928(2) 0.12981(14) 0.0648(6) Uani d . 1 C H3 0.7126 0.4524 0.1769 0.078 Uiso calc R 1 H C4 0.7323(3) 0.4650(2) 0.06610(17) 0.0818(8) Uani d . 1 C H4 0.7822 0.4050 0.0690 0.098 Uiso calc R 1 H C5 0.6995(3) 0.5269(3) -0.00150(17) 0.0860(8) Uani d . 1 C H5 0.7282 0.5072 -0.0444 0.103 Uiso calc R 1 H C6 0.56275(18) 0.61895(16) 0.18759(11) 0.0447(5) Uani d . 1 C C7 0.43578(17) 0.48951(16) 0.32144(11) 0.0453(5) Uani d . 1 C H7 0.4394 0.4202 0.3018 0.054 Uiso calc R 1 H C8 0.37829(17) 0.50592(16) 0.38476(11) 0.0428(5) Uani d . 1 C C9 0.31400(18) 0.42206(16) 0.40672(12) 0.0455(5) Uani d . 1 C H9 0.3105 0.3557 0.3812 0.055 Uiso calc R 1 H C10 0.25516(17) 0.43410(16) 0.46515(12) 0.0450(5) Uani d . 1 C H10 0.2122 0.3765 0.4779 0.054 Uiso calc R 1 H C11 0.25974(16) 0.53213(15) 0.50524(11) 0.0410(4) Uani d . 1 C C12 0.32548(19) 0.61639(17) 0.48372(12) 0.0508(5) Uani d . 1 C H12 0.3306 0.6824 0.5099 0.061 Uiso calc R 1 H C13 0.38248(19) 0.60386(17) 0.42491(12) 0.0517(5) Uani d . 1 C H13 0.4246 0.6617 0.4116 0.062 Uiso calc R 1 H C14 0.17737(17) 0.65909(15) 0.58368(11) 0.0416(4) Uani d . 1 C C15 0.0855(2) 0.71895(17) 0.53250(12) 0.0545(5) Uani d . 1 C H15 0.0387 0.6897 0.4840 0.065 Uiso calc R 1 H C16 0.0632(2) 0.82239(19) 0.55358(14) 0.0630(6) Uani d . 1 C H16 0.0006 0.8621 0.5190 0.076 Uiso calc R 1 H C17 0.1317(2) 0.86850(17) 0.62479(14) 0.0570(6) Uani d . 1 C C18 0.2232(2) 0.80729(19) 0.67450(14) 0.0599(6) Uani d . 1 C H18 0.2707 0.8365 0.7228 0.072 Uiso calc R 1 H C19 0.24604(18) 0.70380(17) 0.65447(13) 0.0521(5) Uani d . 1 C H19 0.3084 0.6640 0.6892 0.063 Uiso calc R 1 H C20 0.1051(3) 0.9814(2) 0.64862(18) 0.0932(10) Uani d . 1 C H20A 0.0921 1.0286 0.6031 0.140 Uiso calc R 1 H H20B 0.1734 1.0069 0.6914 0.140 Uiso calc R 1 H H20C 0.0332 0.9803 0.6665 0.140 Uiso calc R 1 H C21 0.15786(17) 0.46710(15) 0.60601(11) 0.0406(4) Uani d . 1 C C22 0.05155(18) 0.48316(16) 0.62805(12) 0.0477(5) Uani d . 1 C H22 0.0076 0.5468 0.6137 0.057 Uiso calc R 1 H C23 0.01083(19) 0.40604(18) 0.67082(12) 0.0535(5) Uani d . 1 C H23 -0.0607 0.4187 0.6847 0.064 Uiso calc R 1 H C24 0.0727(2) 0.31014(17) 0.69393(12) 0.0520(5) Uani d . 1 C C25 0.17798(19) 0.29433(17) 0.67122(12) 0.0517(5) Uani d . 1 C H25 0.2210 0.2301 0.6850 0.062 Uiso calc R 1 H C26 0.22097(17) 0.37114(16) 0.62879(12) 0.0474(5) Uani d . 1 C H26 0.2928 0.3585 0.6153 0.057 Uiso calc R 1 H C27 0.0287(3) 0.2261(2) 0.74227(18) 0.0862(9) Uani d . 1 C H27A 0.0268 0.2567 0.7926 0.129 Uiso calc R 1 H H27B 0.0835 0.1656 0.7521 0.129 Uiso calc R 1 H H27C -0.0520 0.2027 0.7127 0.129 Uiso calc R 1 H O2 0.49979(17) 0.32773(12) 0.17148(9) 0.0719(5) Uani d . 1 O 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 0.0966(16) 0.0892(17) 0.0511(11) -0.0023(13) 0.0354(11) 0.0032(11) N2 0.0609(10) 0.0393(9) 0.0456(9) 0.0040(8) 0.0275(8) -0.0021(7) N3 0.0532(10) 0.0437(10) 0.0430(9) 0.0041(7) 0.0224(8) -0.0016(7) N4 0.0573(10) 0.0365(9) 0.0570(10) 0.0013(7) 0.0327(8) -0.0024(7) O1 0.0849(11) 0.0413(9) 0.0651(9) 0.0014(7) 0.0360(8) -0.0012(7) C1 0.0699(15) 0.0610(15) 0.0495(12) -0.0028(11) 0.0203(11) 0.0030(10) C2 0.0485(11) 0.0465(12) 0.0449(11) -0.0054(9) 0.0175(9) -0.0012(9) C3 0.0701(15) 0.0687(16) 0.0653(14) 0.0125(12) 0.0349(12) 0.0098(12) C4 0.0888(19) 0.085(2) 0.0904(19) 0.0213(15) 0.0557(16) 0.0025(16) C5 0.101(2) 0.107(2) 0.0695(17) -0.0024(18) 0.0565(16) -0.0085(16) C6 0.0505(11) 0.0408(12) 0.0447(11) -0.0003(9) 0.0168(9) 0.0001(9) C7 0.0524(12) 0.0409(11) 0.0465(11) 0.0049(9) 0.0205(9) 0.0002(9) C8 0.0465(11) 0.0427(11) 0.0430(10) 0.0042(9) 0.0187(9) 0.0010(8) C9 0.0515(11) 0.0383(11) 0.0513(11) 0.0044(9) 0.0220(9) -0.0023(9) C10 0.0483(11) 0.0379(11) 0.0533(11) -0.0008(8) 0.0218(9) 0.0020(9) C11 0.0409(10) 0.0399(11) 0.0463(11) 0.0024(8) 0.0189(9) 0.0011(8) C12 0.0629(13) 0.0412(12) 0.0568(12) -0.0062(9) 0.0310(11) -0.0088(9) C13 0.0619(13) 0.0435(12) 0.0592(12) -0.0085(10) 0.0324(11) -0.0017(10) C14 0.0450(11) 0.0415(11) 0.0450(11) -0.0005(8) 0.0234(9) -0.0018(8) C15 0.0656(14) 0.0520(13) 0.0440(11) 0.0053(11) 0.0132(10) -0.0024(9) C16 0.0798(16) 0.0537(14) 0.0590(14) 0.0214(12) 0.0255(12) 0.0111(11) C17 0.0843(16) 0.0406(12) 0.0616(14) 0.0001(11) 0.0455(13) -0.0003(10) C18 0.0661(14) 0.0582(14) 0.0589(13) -0.0167(12) 0.0235(11) -0.0177(11) C19 0.0456(11) 0.0536(13) 0.0552(12) 0.0001(9) 0.0116(10) -0.0023(10) C20 0.155(3) 0.0478(15) 0.100(2) 0.0112(16) 0.073(2) -0.0044(14) C21 0.0435(10) 0.0394(11) 0.0415(10) -0.0034(8) 0.0165(8) -0.0033(8) C22 0.0507(12) 0.0436(11) 0.0543(12) 0.0033(9) 0.0242(10) -0.0031(9) C23 0.0567(13) 0.0558(13) 0.0606(13) -0.0025(10) 0.0369(11) -0.0071(11) C24 0.0682(14) 0.0478(12) 0.0492(11) -0.0063(10) 0.0314(11) -0.0035(9) C25 0.0588(13) 0.0443(12) 0.0539(12) 0.0041(10) 0.0193(10) 0.0046(9) C26 0.0416(11) 0.0514(12) 0.0534(12) 0.0046(9) 0.0203(9) 0.0021(9) C27 0.120(2) 0.0624(17) 0.102(2) 0.0002(15) 0.0743(19) 0.0110(14) O2 0.1127(13) 0.0446(9) 0.0583(9) -0.0071(9) 0.0248(9) 0.0048(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_publ_flag C1 N1 C5 116.0(2) ? C6 N2 N3 119.07(16) yes C6 N2 H2 120.5 ? N3 N2 H2 120.5 ? C7 N3 N2 115.21(16) yes C11 N4 C21 124.90(15) yes C11 N4 C14 118.64(15) yes C21 N4 C14 116.45(15) yes N1 C1 C2 125.0(2) ? N1 C1 H1 117.5 ? C2 C1 H1 117.5 ? C1 C2 C3 117.2(2) ? C1 C2 C6 118.62(19) ? C3 C2 C6 124.21(18) ? C4 C3 C2 119.2(2) ? C4 C3 H3 120.4 ? C2 C3 H3 120.4 ? C5 C4 C3 118.8(3) ? C5 C4 H4 120.6 ? C3 C4 H4 120.6 ? N1 C5 C4 123.9(2) ? N1 C5 H5 118.0 ? C4 C5 H5 118.0 ? O1 C6 N2 123.94(18) yes O1 C6 C2 120.85(18) yes N2 C6 C2 115.21(17) yes N3 C7 C8 121.76(18) yes N3 C7 H7 119.1 ? C8 C7 H7 119.1 ? C9 C8 C13 117.29(17) ? C9 C8 C7 119.71(18) ? C13 C8 C7 122.99(18) ? C10 C9 C8 122.08(18) ? C10 C9 H9 119.0 ? C8 C9 H9 119.0 ? C9 C10 C11 120.44(18) ? C9 C10 H10 119.8 ? C11 C10 H10 119.8 ? C10 C11 C12 117.55(17) ? C10 C11 N4 122.98(17) ? C12 C11 N4 119.46(17) ? C13 C12 C11 121.51(18) ? C13 C12 H12 119.2 ? C11 C12 H12 119.2 ? C12 C13 C8 121.13(19) ? C12 C13 H13 119.4 ? C8 C13 H13 119.4 ? C19 C14 C15 119.39(19) ? C19 C14 N4 120.02(18) ? C15 C14 N4 120.58(17) ? C16 C15 C14 119.7(2) ? C16 C15 H15 120.2 ? C14 C15 H15 120.2 ? C15 C16 C17 121.6(2) ? C15 C16 H16 119.2 ? C17 C16 H16 119.2 ? C18 C17 C16 117.6(2) ? C18 C17 C20 121.0(2) ? C16 C17 C20 121.4(2) ? C17 C18 C19 121.5(2) ? C17 C18 H18 119.2 ? C19 C18 H18 119.2 ? C14 C19 C18 120.3(2) ? C14 C19 H19 119.9 ? C18 C19 H19 119.9 ? C17 C20 H20A 109.5 ? C17 C20 H20B 109.5 ? H20A C20 H20B 109.5 ? C17 C20 H20C 109.5 ? H20A C20 H20C 109.5 ? H20B C20 H20C 109.5 ? C26 C21 C22 117.85(18) ? C26 C21 N4 122.65(17) ? C22 C21 N4 119.47(17) ? C23 C22 C21 120.69(19) ? C23 C22 H22 119.7 ? C21 C22 H22 119.7 ? C22 C23 C24 122.09(19) ? C22 C23 H23 119.0 ? C24 C23 H23 119.0 ? C23 C24 C25 116.91(19) ? C23 C24 C27 121.9(2) ? C25 C24 C27 121.1(2) ? C26 C25 C24 121.91(19) ? C26 C25 H25 119.0 ? C24 C25 H25 119.0 ? C25 C26 C21 120.55(18) ? C25 C26 H26 119.7 ? C21 C26 H26 119.7 ? C24 C27 H27A 109.5 ? C24 C27 H27B 109.5 ? H27A C27 H27B 109.5 ? C24 C27 H27C 109.5 ? H27A C27 H27C 109.5 ? H27B C27 H27C 109.5 ? H2A O2 H2B 109.3 yes loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag N1 C1 1.323(3) yes N1 C5 1.337(4) yes N2 C6 1.343(2) yes N2 N3 1.386(2) yes N2 H2 0.8600 ? N3 C7 1.278(2) yes N4 C11 1.400(2) yes N4 C21 1.422(2) yes N4 C14 1.441(2) yes O1 C6 1.229(2) yes C1 C2 1.378(3) ? C1 H1 0.9300 ? C2 C3 1.380(3) ? C2 C6 1.492(3) ? C3 C4 1.371(3) ? C3 H3 0.9300 ? C4 C5 1.361(4) ? C4 H4 0.9300 ? C5 H5 0.9300 ? C7 C8 1.451(3) yes C7 H7 0.9300 ? C8 C9 1.389(3) ? C8 C13 1.395(3) ? C9 C10 1.379(3) ? C9 H9 0.9300 ? C10 C11 1.395(3) ? C10 H10 0.9300 ? C11 C12 1.400(3) ? C12 C13 1.371(3) ? C12 H12 0.9300 ? C13 H13 0.9300 ? C14 C19 1.369(3) ? C14 C15 1.378(3) ? C15 C16 1.378(3) ? C15 H15 0.9300 ? C16 C17 1.380(3) ? C16 H16 0.9300 ? C17 C18 1.374(3) ? C17 C20 1.516(3) ? C18 C19 1.375(3) ? C18 H18 0.9300 ? C19 H19 0.9300 ? C20 H20A 0.9600 ? C20 H20B 0.9600 ? C20 H20C 0.9600 ? C21 C26 1.388(3) ? C21 C22 1.390(3) ? C22 C23 1.373(3) ? C22 H22 0.9300 ? C23 C24 1.382(3) ? C23 H23 0.9300 ? C24 C25 1.384(3) ? C24 C27 1.514(3) ? C25 C26 1.380(3) ? C25 H25 0.9300 ? C26 H26 0.9300 ? C27 H27A 0.9600 ? C27 H27B 0.9600 ? C27 H27C 0.9600 ? O2 H2A 0.8561 yes O2 H2B 0.8539 yes 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 N2 H2 O2 . 0.86 1.99 2.810(2) 160 O2 H2A N1 3_665 0.86 2.23 2.853(3) 129 O2 H2B O1 2_645 0.85 2.12 2.845(2) 142 O2 H2B N3 2_645 0.85 2.54 3.282(2) 147 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_publ_flag C6 N2 N3 C7 169.97(18) yes C5 N1 C1 C2 0.3(4) ? N1 C1 C2 C3 0.8(3) ? N1 C1 C2 C6 -179.6(2) ? C1 C2 C3 C4 -1.3(3) ? C6 C2 C3 C4 179.1(2) ? C2 C3 C4 C5 0.9(4) ? C1 N1 C5 C4 -0.7(4) ? C3 C4 C5 N1 0.2(5) ? N3 N2 C6 O1 -1.6(3) yes N3 N2 C6 C2 179.14(15) yes C1 C2 C6 O1 -35.7(3) ? C3 C2 C6 O1 143.9(2) ? C1 C2 C6 N2 143.5(2) ? C3 C2 C6 N2 -36.8(3) ? N2 N3 C7 C8 -178.03(16) yes N3 C7 C8 C9 170.50(19) ? N3 C7 C8 C13 -8.5(3) ? C13 C8 C9 C10 0.6(3) ? C7 C8 C9 C10 -178.41(18) ? C8 C9 C10 C11 -0.8(3) ? C9 C10 C11 C12 0.1(3) ? C9 C10 C11 N4 178.73(17) ? C21 N4 C11 C10 18.6(3) ? C14 N4 C11 C10 -160.90(18) ? C21 N4 C11 C12 -162.82(18) ? C14 N4 C11 C12 17.7(3) ? C10 C11 C12 C13 0.6(3) ? N4 C11 C12 C13 -178.03(19) ? C11 C12 C13 C8 -0.7(3) ? C9 C8 C13 C12 0.1(3) ? C7 C8 C13 C12 179.13(19) ? C11 N4 C14 C19 -105.6(2) ? C21 N4 C14 C19 74.9(2) ? C11 N4 C14 C15 75.6(2) ? C21 N4 C14 C15 -103.9(2) ? C19 C14 C15 C16 -0.6(3) ? N4 C14 C15 C16 178.22(19) ? C14 C15 C16 C17 0.6(4) ? C15 C16 C17 C18 -0.2(3) ? C15 C16 C17 C20 -178.6(2) ? C16 C17 C18 C19 -0.1(3) ? C20 C17 C18 C19 178.3(2) ? C15 C14 C19 C18 0.3(3) ? N4 C14 C19 C18 -178.55(19) ? C17 C18 C19 C14 0.1(3) ? C11 N4 C21 C26 36.1(3) ? C14 N4 C21 C26 -144.41(19) ? C11 N4 C21 C22 -146.10(19) ? C14 N4 C21 C22 33.4(2) ? C26 C21 C22 C23 -0.1(3) ? N4 C21 C22 C23 -178.07(18) ? C21 C22 C23 C24 0.2(3) ? C22 C23 C24 C25 -0.7(3) ? C22 C23 C24 C27 179.0(2) ? C23 C24 C25 C26 1.2(3) ? C27 C24 C25 C26 -178.5(2) ? C24 C25 C26 C21 -1.2(3) ? C22 C21 C26 C25 0.6(3) ? N4 C21 C26 C25 178.50(18) ? loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 21174364 2 PubChem 139066578