#------------------------------------------------------------------------------ #$Date: 2025-08-19 15:49:58 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301806 $ #$URL: svn://www.crystallography.net/cod/cif/2/23/89/2238926.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_2238926 loop_ _publ_author_name 'Suwunwong, Thitipone' 'Chantrapromma, Suchada' 'Quah, Ching Kheng' 'Fun, Hoong-Kun' _publ_section_title ; 6-(4-Aminophenyl)-2-methoxy-4-phenylnicotinonitrile ; _journal_coeditor_code SJ5368 _journal_issue 12 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o1816 _journal_page_last o1817 _journal_paper_doi 10.1107/S1600536813031437 _journal_volume 69 _journal_year 2013 _chemical_formula_iupac 'C19 H15 N3 O' _chemical_formula_moiety 'C19 H15 N3 O' _chemical_formula_sum 'C19 H15 N3 O' _chemical_formula_weight 301.34 _chemical_melting_point_gt 475 _chemical_melting_point_lt 476 _chemical_name_systematic ; 6-(4-Aminophenyl)-2-methoxy-4-phenylnicotinonitrile ; _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 94.743(2) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 10.9448(12) _cell_length_b 18.960(2) _cell_length_c 7.4738(8) _cell_measurement_reflns_used 3696 _cell_measurement_temperature 100 _cell_measurement_theta_max 27.99 _cell_measurement_theta_min 2.15 _cell_volume 1545.6(3) _computing_cell_refinement 'SAINT (Bruker, 2009)' _computing_data_collection 'APEX2 (Bruker, 2009)' _computing_data_reduction 'SAINT (Bruker, 2009)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material ; SHELXTL (Sheldrick, 2008), PLATON (Spek, 2009), Mercury (Macrae et al., 2006) and publCIF (Westrip, 2010) ; _computing_structure_refinement 'SHELXTL (Sheldrick, 2008)' _computing_structure_solution 'SHELXTL (Sheldrick, 2008)' _diffrn_ambient_temperature 100 _diffrn_measured_fraction_theta_full 0.995 _diffrn_measured_fraction_theta_max 0.995 _diffrn_measurement_device_type 'Bruker APEX DUO CCD area-detector' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0511 _diffrn_reflns_av_sigmaI/netI 0.0471 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_number 14200 _diffrn_reflns_theta_full 27.99 _diffrn_reflns_theta_max 27.99 _diffrn_reflns_theta_min 2.15 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_T_max 0.9954 _exptl_absorpt_correction_T_min 0.9550 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Bruker, 2009)' _exptl_crystal_colour Yellow _exptl_crystal_density_diffrn 1.295 _exptl_crystal_density_method 'not measured' _exptl_crystal_description Plate _exptl_crystal_F_000 632 _exptl_crystal_size_max 0.56 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.06 _refine_diff_density_max 0.299 _refine_diff_density_min -0.284 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.066 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 217 _refine_ls_number_reflns 3696 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.066 _refine_ls_R_factor_all 0.0676 _refine_ls_R_factor_gt 0.0457 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0815P)^2^+0.0098P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1274 _refine_ls_wR_factor_ref 0.1425 _reflns_number_gt 2689 _reflns_number_total 3696 _reflns_threshold_expression I>2\s(I) _iucr_refine_instructions_details ; TITL mo_tniam1a_0m in P2(1)/c (100K) CELL 0.71073 10.9448 18.9598 7.4738 90.000 94.743 90.000 ZERR 4.00 0.0012 0.0022 0.0008 0.000 0.002 0.000 LATT 1 SYMM -X, 0.5+Y, 0.5-Z SFAC C H N O UNIT 76 60 12 4 TEMP -173.000 SIZE 0.056 0.168 0.563 L.S. 10 OMIT -4 56 BOND $H FMAP 2 3 60 ACTA CONF PLAN 20 REM mo_tniam1a_0m in P2(1)/c (100K) REM R1 = 0.1280 for 2700 Fo > 4sig(Fo) and 0.1551 for all 3708 data REM 129 parameters refined using 0 restraints WGHT 0.081500 0.009800 FVAR 0.40230 O1 4 0.413339 0.118859 0.324837 11.00000 0.02349 0.01587 = 0.02985 -0.00053 -0.00087 -0.00032 N1 3 0.874425 0.472583 0.599048 11.00000 0.02088 0.02073 = 0.04009 0.00337 -0.00152 -0.00281 H2N1 2 0.948046 0.449759 0.618777 11.00000 0.03643 H1N1 2 0.877554 0.516994 0.554368 11.00000 0.04254 N2 3 0.484832 0.231809 0.377390 11.00000 0.02205 0.01727 = 0.01951 -0.00081 0.00097 -0.00071 N3 3 0.127531 0.116896 0.117338 11.00000 0.02582 0.02264 = 0.02979 -0.00122 0.00063 -0.00151 C1 1 0.569140 0.347567 0.429493 11.00000 0.01901 0.02012 = 0.01722 -0.00220 0.00185 -0.00038 C2 1 0.568603 0.420588 0.400948 11.00000 0.01898 0.02122 = 0.02307 0.00082 0.00089 0.00170 AFIX 43 H2A 2 0.497414 0.442112 0.343522 11.00000 -1.20000 AFIX 0 C3 1 0.668765 0.462162 0.454020 11.00000 0.02233 0.01665 = 0.02767 0.00027 0.00203 0.00006 AFIX 43 H3A 2 0.665923 0.511504 0.431957 11.00000 -1.20000 AFIX 0 C4 1 0.774838 0.431726 0.540523 11.00000 0.01920 0.02132 = 0.02301 -0.00100 0.00327 -0.00247 C5 1 0.775923 0.358852 0.571461 11.00000 0.01969 0.02068 = 0.02846 0.00041 -0.00103 0.00039 AFIX 43 H5A 2 0.846458 0.337417 0.631029 11.00000 -1.20000 AFIX 0 C6 1 0.675516 0.317838 0.516268 11.00000 0.02260 0.01689 = 0.02596 0.00061 0.00231 0.00043 AFIX 43 H6A 2 0.678537 0.268443 0.537506 11.00000 -1.20000 AFIX 0 C7 1 0.464278 0.302465 0.369159 11.00000 0.02312 0.01835 = 0.01614 -0.00097 0.00291 -0.00076 C8 1 0.349494 0.329422 0.308454 11.00000 0.02252 0.01628 = 0.01904 -0.00129 0.00167 -0.00001 AFIX 43 H8A 2 0.336469 0.378962 0.308013 11.00000 -1.20000 AFIX 0 C9 1 0.253832 0.284575 0.248523 11.00000 0.02078 0.02025 = 0.01545 -0.00107 0.00280 -0.00107 C10 1 0.131132 0.313688 0.189780 11.00000 0.02245 0.02137 = 0.01695 -0.00564 -0.00210 0.00102 C11 1 0.024592 0.282727 0.245118 11.00000 0.02410 0.02603 = 0.02327 -0.00770 0.00102 -0.00076 AFIX 43 H11A 2 0.030089 0.241964 0.319263 11.00000 -1.20000 AFIX 0 C12 1 -0.089132 0.311526 0.191765 11.00000 0.02287 0.03628 = 0.03480 -0.01499 -0.00020 0.00098 AFIX 43 H12A 2 -0.161261 0.290863 0.231285 11.00000 -1.20000 AFIX 0 C13 1 -0.098118 0.370354 0.080981 11.00000 0.03141 0.03470 = 0.04144 -0.01536 -0.01055 0.01140 AFIX 43 H13A 2 -0.176287 0.389424 0.043187 11.00000 -1.20000 AFIX 0 C14 1 0.006947 0.401169 0.025695 11.00000 0.04242 0.02383 = 0.03230 -0.00556 -0.01013 0.00992 AFIX 43 H14A 2 0.000781 0.441304 -0.050614 11.00000 -1.20000 AFIX 0 C15 1 0.121529 0.373628 0.081378 11.00000 0.03160 0.01998 = 0.02353 -0.00517 -0.00229 0.00099 AFIX 43 H15A 2 0.193500 0.395699 0.045488 11.00000 -1.20000 AFIX 0 C16 1 0.395247 0.189277 0.319680 11.00000 0.02396 0.01630 = 0.01769 0.00058 0.00413 -0.00137 C17 1 0.278047 0.211803 0.250351 11.00000 0.01971 0.02125 = 0.01792 -0.00110 0.00152 -0.00251 C18 1 0.192703 0.160110 0.176866 11.00000 0.02241 0.01943 = 0.02010 0.00048 0.00159 0.00013 C19 1 0.533840 0.095271 0.391920 11.00000 0.02797 0.01987 = 0.02775 0.00259 0.00042 0.00304 AFIX 137 H19A 2 0.537281 0.043663 0.387003 11.00000 -1.50000 H19B 2 0.550940 0.110938 0.516429 11.00000 -1.50000 H19C 2 0.595154 0.115188 0.317896 11.00000 -1.50000 HKLF 4 1 0 0 1 0 -1 0 1 0 0 REM mo_tniam1a_0m in P2(1)/c (100K) REM R1 = 0.0457 for 2689 Fo > 4sig(Fo) and 0.0676 for all 3696 data REM 217 parameters refined using 0 restraints END WGHT 0.0815 0.0098 REM Highest difference peak 0.299, deepest hole -0.284, 1-sigma level 0.056 Q1 1 0.4170 0.3203 0.2967 11.00000 0.05 0.30 Q2 1 0.1885 0.3001 0.2383 11.00000 0.05 0.30 Q3 1 0.3226 0.2003 0.3217 11.00000 0.05 0.27 Q4 1 0.7637 0.3406 0.3642 11.00000 0.05 0.24 Q5 1 0.3177 0.3033 0.2369 11.00000 0.05 0.24 Q6 1 0.6359 0.3322 0.4147 11.00000 0.05 0.23 Q7 1 0.7342 0.4484 0.4426 11.00000 0.05 0.22 Q8 1 0.3441 0.2029 0.2467 11.00000 0.05 0.22 Q9 1 0.6415 0.4329 0.3860 11.00000 0.05 0.21 Q10 1 0.6953 0.5196 0.3748 11.00000 0.05 0.20 Q11 1 0.8861 0.4643 0.7637 11.00000 0.05 0.20 Q12 1 -0.0184 0.2987 0.1921 11.00000 0.05 0.20 Q13 1 0.7092 0.3428 0.5821 11.00000 0.05 0.19 Q14 1 0.3419 0.3422 0.5173 11.00000 0.05 0.19 Q15 1 -0.2110 0.3851 0.0964 11.00000 0.05 0.18 Q16 1 0.2853 0.3027 0.3286 11.00000 0.05 0.18 Q17 1 0.2571 0.1784 0.1712 11.00000 0.05 0.18 Q18 1 0.3225 0.3193 0.1205 11.00000 0.05 0.17 Q19 1 0.5168 0.3238 0.4027 11.00000 0.05 0.17 Q20 1 0.6383 0.0323 0.4621 11.00000 0.05 0.17 ; _cod_data_source_file sj5368.cif _cod_data_source_block I _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 2238926 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 O O1 0.41334(9) 0.11886(5) 0.32484(15) 0.0232(3) Uani d . 1 1 N N1 0.87443(12) 0.47258(7) 0.5990(2) 0.0275(3) Uani d . 1 1 H H2N1 0.9480(17) 0.4498(10) 0.619(3) 0.036(5) Uiso d . 1 1 H H1N1 0.8776(17) 0.5170(11) 0.554(3) 0.043(6) Uiso d . 1 1 N N2 0.48483(11) 0.23181(6) 0.37739(17) 0.0197(3) Uani d . 1 1 N N3 0.12753(11) 0.11690(6) 0.1173(2) 0.0262(3) Uani d . 1 1 C C1 0.56914(12) 0.34757(7) 0.4295(2) 0.0188(3) Uani d . 1 1 C C2 0.56860(13) 0.42059(7) 0.4009(2) 0.0211(3) Uani d . 1 1 H H2A 0.4974 0.4421 0.3435 0.025 Uiso calc R 1 1 C C3 0.66877(13) 0.46216(7) 0.4540(2) 0.0222(3) Uani d . 1 1 H H3A 0.6659 0.5115 0.4320 0.027 Uiso calc R 1 1 C C4 0.77484(13) 0.43173(7) 0.5405(2) 0.0211(3) Uani d . 1 1 C C5 0.77592(13) 0.35885(8) 0.5715(2) 0.0231(3) Uani d . 1 1 H H5A 0.8465 0.3374 0.6310 0.028 Uiso calc R 1 1 C C6 0.67552(13) 0.31784(7) 0.5163(2) 0.0218(3) Uani d . 1 1 H H6A 0.6785 0.2684 0.5375 0.026 Uiso calc R 1 1 C C7 0.46428(12) 0.30246(7) 0.3692(2) 0.0191(3) Uani d . 1 1 C C8 0.34949(13) 0.32942(7) 0.3085(2) 0.0193(3) Uani d . 1 1 H H8A 0.3365 0.3790 0.3080 0.023 Uiso calc R 1 1 C C9 0.25383(12) 0.28457(7) 0.2485(2) 0.0188(3) Uani d . 1 1 C C10 0.13113(13) 0.31369(7) 0.1898(2) 0.0205(3) Uani d . 1 1 C C11 0.02459(13) 0.28273(8) 0.2451(2) 0.0245(3) Uani d . 1 1 H H11A 0.0301 0.2420 0.3193 0.029 Uiso calc R 1 1 C C12 -0.08913(14) 0.31153(9) 0.1918(2) 0.0315(4) Uani d . 1 1 H H12A -0.1613 0.2909 0.2313 0.038 Uiso calc R 1 1 C C13 -0.09812(16) 0.37035(9) 0.0810(3) 0.0366(5) Uani d . 1 1 H H13A -0.1763 0.3894 0.0432 0.044 Uiso calc R 1 1 C C14 0.00695(16) 0.40117(8) 0.0257(3) 0.0336(4) Uani d . 1 1 H H14A 0.0008 0.4413 -0.0506 0.040 Uiso calc R 1 1 C C15 0.12153(14) 0.37363(8) 0.0814(2) 0.0253(4) Uani d . 1 1 H H15A 0.1935 0.3957 0.0455 0.030 Uiso calc R 1 1 C C16 0.39525(12) 0.18928(7) 0.3197(2) 0.0192(3) Uani d . 1 1 C C17 0.27805(12) 0.21180(7) 0.2504(2) 0.0196(3) Uani d . 1 1 C C18 0.19270(13) 0.16011(7) 0.1769(2) 0.0207(3) Uani d . 1 1 C C19 0.53384(14) 0.09527(8) 0.3919(2) 0.0253(4) Uani d . 1 1 H H19A 0.5373 0.0437 0.3870 0.038 Uiso calc R 1 1 H H19B 0.5509 0.1109 0.5164 0.038 Uiso calc R 1 1 H H19C 0.5952 0.1152 0.3179 0.038 Uiso calc R 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 O1 0.0235(5) 0.0159(5) 0.0299(7) -0.0003(4) -0.0009(5) -0.0005(4) N1 0.0209(7) 0.0207(6) 0.0401(9) -0.0028(5) -0.0015(6) 0.0034(6) N2 0.0220(6) 0.0173(6) 0.0195(7) -0.0007(4) 0.0010(5) -0.0008(5) N3 0.0258(7) 0.0226(6) 0.0298(8) -0.0015(5) 0.0006(6) -0.0012(6) C1 0.0190(7) 0.0201(7) 0.0172(8) -0.0004(5) 0.0018(6) -0.0022(6) C2 0.0190(7) 0.0212(7) 0.0231(8) 0.0017(5) 0.0009(6) 0.0008(6) C3 0.0223(7) 0.0166(6) 0.0277(9) 0.0001(5) 0.0020(6) 0.0003(6) C4 0.0192(7) 0.0213(7) 0.0230(8) -0.0025(5) 0.0033(6) -0.0010(6) C5 0.0197(7) 0.0207(7) 0.0285(9) 0.0004(5) -0.0010(6) 0.0004(6) C6 0.0226(7) 0.0169(6) 0.0260(9) 0.0004(5) 0.0023(6) 0.0006(6) C7 0.0231(7) 0.0183(6) 0.0161(8) -0.0008(5) 0.0029(6) -0.0010(6) C8 0.0225(7) 0.0163(6) 0.0190(8) 0.0000(5) 0.0017(6) -0.0013(6) C9 0.0208(7) 0.0202(7) 0.0155(8) -0.0011(5) 0.0028(5) -0.0011(6) C10 0.0225(7) 0.0214(7) 0.0169(8) 0.0010(5) -0.0021(6) -0.0056(6) C11 0.0241(7) 0.0260(7) 0.0233(9) -0.0008(6) 0.0010(6) -0.0077(7) C12 0.0229(8) 0.0363(8) 0.0348(10) 0.0010(6) -0.0002(7) -0.0150(8) C13 0.0314(9) 0.0347(9) 0.0414(11) 0.0114(7) -0.0105(8) -0.0154(8) C14 0.0424(9) 0.0238(7) 0.0323(10) 0.0099(7) -0.0101(8) -0.0056(7) C15 0.0316(8) 0.0200(7) 0.0235(9) 0.0010(6) -0.0023(7) -0.0052(6) C16 0.0240(7) 0.0163(6) 0.0177(8) -0.0014(5) 0.0041(6) 0.0006(6) C17 0.0197(7) 0.0212(7) 0.0179(8) -0.0025(5) 0.0015(6) -0.0011(6) C18 0.0224(7) 0.0194(6) 0.0201(8) 0.0001(5) 0.0016(6) 0.0005(6) C19 0.0280(8) 0.0199(7) 0.0277(9) 0.0030(6) 0.0004(6) 0.0026(6) 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 C16 O1 C19 116.38(10) C4 N1 H2N1 116.6(11) C4 N1 H1N1 117.2(12) H2N1 N1 H1N1 116.0(17) C16 N2 C7 118.28(12) C2 C1 C6 117.41(12) C2 C1 C7 122.29(12) C6 C1 C7 120.29(12) C3 C2 C1 121.80(13) C3 C2 H2A 119.1 C1 C2 H2A 119.1 C2 C3 C4 120.24(13) C2 C3 H3A 119.9 C4 C3 H3A 119.9 N1 C4 C5 120.41(13) N1 C4 C3 121.11(13) C5 C4 C3 118.45(12) C6 C5 C4 120.69(13) C6 C5 H5A 119.7 C4 C5 H5A 119.7 C5 C6 C1 121.41(13) C5 C6 H6A 119.3 C1 C6 H6A 119.3 N2 C7 C8 121.10(12) N2 C7 C1 115.91(12) C8 C7 C1 122.99(12) C9 C8 C7 120.85(12) C9 C8 H8A 119.6 C7 C8 H8A 119.6 C8 C9 C17 117.39(12) C8 C9 C10 120.36(12) C17 C9 C10 122.24(12) C15 C10 C11 119.30(13) C15 C10 C9 119.85(13) C11 C10 C9 120.84(14) C12 C11 C10 120.01(15) C12 C11 H11A 120.0 C10 C11 H11A 120.0 C11 C12 C13 120.37(16) C11 C12 H12A 119.8 C13 C12 H12A 119.8 C14 C13 C12 119.87(15) C14 C13 H13A 120.1 C12 C13 H13A 120.1 C13 C14 C15 120.24(16) C13 C14 H14A 119.9 C15 C14 H14A 119.9 C14 C15 C10 120.19(16) C14 C15 H15A 119.9 C10 C15 H15A 119.9 N2 C16 O1 119.59(12) N2 C16 C17 124.49(13) O1 C16 C17 115.92(12) C9 C17 C16 117.80(12) C9 C17 C18 123.51(12) C16 C17 C18 118.60(13) N3 C18 C17 177.54(15) O1 C19 H19A 109.5 O1 C19 H19B 109.5 H19A C19 H19B 109.5 O1 C19 H19C 109.5 H19A C19 H19C 109.5 H19B C19 H19C 109.5 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O1 C16 1.3498(16) O1 C19 1.4427(17) N1 C4 1.3786(18) N1 H2N1 0.916(19) N1 H1N1 0.91(2) N2 C16 1.3144(17) N2 C7 1.3589(17) N3 C18 1.1513(18) C1 C2 1.401(2) C1 C6 1.4032(18) C1 C7 1.4718(18) C2 C3 1.3815(19) C2 H2A 0.9500 C3 C4 1.4052(19) C3 H3A 0.9500 C4 C5 1.401(2) C5 C6 1.3811(19) C5 H5A 0.9500 C6 H6A 0.9500 C7 C8 1.3968(19) C8 C9 1.3937(18) C8 H8A 0.9500 C9 C17 1.405(2) C9 C10 1.4844(18) C10 C15 1.395(2) C10 C11 1.398(2) C11 C12 1.387(2) C11 H11A 0.9500 C12 C13 1.388(3) C12 H12A 0.9500 C13 C14 1.383(3) C13 H13A 0.9500 C14 C15 1.390(2) C14 H14A 0.9500 C15 H15A 0.9500 C16 C17 1.4094(19) C17 C18 1.4317(19) C19 H19A 0.9800 C19 H19B 0.9800 C19 H19C 0.9800 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 _geom_hbond_publ_flag N1 H2N1 N3 4_666 0.915(19) 2.338(19) 3.2416(18) 169.5(19) y N1 H1N1 N3 2_655 0.91(2) 2.28(2) 3.1773(19) 168(2) y C11 H11A Cg3 4_555 0.95 2.87 3.7667(17) 158 y C19 H19C Cg2 4_554 0.98 2.69 3.5156(17) 142 y 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 C6 C1 C2 C3 0.6(2) C7 C1 C2 C3 -178.29(15) C1 C2 C3 C4 -0.5(2) C2 C3 C4 N1 -178.14(15) C2 C3 C4 C5 -0.2(2) N1 C4 C5 C6 178.73(16) C3 C4 C5 C6 0.7(2) C4 C5 C6 C1 -0.7(2) C2 C1 C6 C5 0.0(2) C7 C1 C6 C5 178.90(15) C16 N2 C7 C8 2.8(2) C16 N2 C7 C1 -177.88(13) C2 C1 C7 N2 169.00(15) C6 C1 C7 N2 -9.9(2) C2 C1 C7 C8 -11.7(2) C6 C1 C7 C8 169.48(15) N2 C7 C8 C9 -2.3(2) C1 C7 C8 C9 178.41(14) C7 C8 C9 C17 -0.5(2) C7 C8 C9 C10 178.05(14) C8 C9 C10 C15 43.4(2) C17 C9 C10 C15 -138.05(15) C8 C9 C10 C11 -135.09(16) C17 C9 C10 C11 43.4(2) C15 C10 C11 C12 0.2(2) C9 C10 C11 C12 178.71(14) C10 C11 C12 C13 1.1(2) C11 C12 C13 C14 -1.0(3) C12 C13 C14 C15 -0.3(3) C13 C14 C15 C10 1.6(3) C11 C10 C15 C14 -1.5(2) C9 C10 C15 C14 179.94(14) C7 N2 C16 O1 179.46(13) C7 N2 C16 C17 -0.5(2) C19 O1 C16 N2 -1.2(2) C19 O1 C16 C17 178.69(14) C8 C9 C17 C16 2.7(2) C10 C9 C17 C16 -175.87(14) C8 C9 C17 C18 -173.75(14) C10 C9 C17 C18 7.7(2) N2 C16 C17 C9 -2.3(2) O1 C16 C17 C9 177.76(14) N2 C16 C17 C18 174.30(15) O1 C16 C17 C18 -5.6(2) loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 89105566