#------------------------------------------------------------------------------ #$Date: 2016-02-20 03:06:23 +0000 (Sat, 20 Feb 2016) $ #$Revision: 176774 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/24/2202454.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_2202454 loop_ _publ_author_name 'You, Zhong-Lu' 'Zhu, Hai-Liang' 'Liu, Wei-Sheng' 'Tan, Min-Yu' _publ_section_title ;{2-[(1,5-Dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-ylimino)methyl]phenoxy}acetic acid nitrate ; _journal_issue 12 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o1920 _journal_page_last o1922 _journal_paper_doi 10.1107/S1600536803025339 _journal_volume 59 _journal_year 2003 _chemical_formula_iupac 'C20 H20 N3 O4 1+, N O3 1-' _chemical_formula_moiety 'C20 H20 N3 O4 1+, N O3 1-' _chemical_formula_sum 'C20 H20 N4 O7' _chemical_formula_weight 428.40 _chemical_name_systematic ; {2-[(1,5-Dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4- ylimino)methyl]phenoxy}acetic acid nitrate ; _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 97.608(7) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 7.102(3) _cell_length_b 11.110(5) _cell_length_c 25.177(10) _cell_measurement_reflns_used 1434 _cell_measurement_temperature 298(2) _cell_measurement_theta_max 21.53 _cell_measurement_theta_min 3.129 _cell_volume 1969.1(14) _computing_cell_refinement SMART _computing_data_collection 'SMART (Siemens, 1996)' _computing_data_reduction 'SAINT (Siemens, 1996)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 1997b)' _computing_publication_material SHELXTL _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997a)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997a)' _diffrn_ambient_temperature 298(2) _diffrn_measured_fraction_theta_full 0.973 _diffrn_measured_fraction_theta_max 0.973 _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 0.0501 _diffrn_reflns_av_sigmaI/netI 0.0674 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_number 9917 _diffrn_reflns_theta_full 25.03 _diffrn_reflns_theta_max 25.03 _diffrn_reflns_theta_min 2.45 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.111 _exptl_absorpt_correction_T_max 0.9770 _exptl_absorpt_correction_T_min 0.9599 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.445 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 896 _exptl_crystal_size_max 0.37 _exptl_crystal_size_mid 0.29 _exptl_crystal_size_min 0.21 _refine_diff_density_max 0.568 _refine_diff_density_min -0.316 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.890 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 360 _refine_ls_number_reflns 3390 _refine_ls_number_restraints 12 _refine_ls_restrained_S_all 0.889 _refine_ls_R_factor_all 0.1193 _refine_ls_R_factor_gt 0.0653 _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^)+(0.1199P)^2^] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1688 _refine_ls_wR_factor_ref 0.1980 _reflns_number_gt 1737 _reflns_number_total 3390 _reflns_threshold_expression I>2\s(I) _cod_data_source_file cf6298.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 ; _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 2202454 _cod_database_fobs_code 2202454 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_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol N1 0.8003(4) 0.6942(3) 0.33515(11) 0.0466(8) Uani d . 1 . . N N2 0.9547(4) 0.6501(3) 0.31210(11) 0.0498(8) Uani d . 1 . . N N3 0.9441(5) 0.4397(3) 0.41756(12) 0.0445(8) Uani d . 1 . . N N4 0.9560(6) 0.1406(4) 0.35655(15) 0.0652(10) Uani d . 1 . . N O1 0.6318(4) 0.6292(2) 0.40320(10) 0.0599(8) Uani d . 1 . . O O2 1.4450(4) 0.3015(3) 0.41444(12) 0.0739(9) Uani d . 1 . . O O3 1.5536(5) 0.1141(3) 0.43005(13) 0.0768(9) Uani d . 1 . . O O4 1.1514(4) 0.2580(2) 0.46914(9) 0.0510(7) Uani d . 1 . . O O5 0.8697(6) 0.1055(6) 0.39121(18) 0.150(2) Uani d . 1 . . O O6 0.9611(12) 0.2446(5) 0.34836(17) 0.197(3) Uani d . 1 . . O O7 1.0510(11) 0.0851(7) 0.3354(2) 0.225(4) Uani d . 1 . . O C1 0.7671(5) 0.6185(3) 0.37708(13) 0.0451(9) Uani d . 1 . . C C2 0.9165(5) 0.5325(3) 0.38003(13) 0.0451(9) Uani d . 1 . . C C3 1.0302(5) 0.5570(3) 0.34126(13) 0.0430(9) Uani d . 1 . . C C4 1.4363(5) 0.2042(4) 0.43469(16) 0.0541(10) Uani d . 1 . . C C5 1.2932(6) 0.1686(4) 0.47119(19) 0.0574(11) Uani d . 1 . . C C6 0.8462(5) 0.4252(4) 0.45742(14) 0.0465(9) Uani d . 1 . . C C7 0.8697(5) 0.3318(3) 0.49701(13) 0.0419(9) Uani d . 1 . . C C8 1.0161(5) 0.2442(3) 0.50208(13) 0.0437(9) Uani d . 1 . . C C9 1.0169(6) 0.1551(4) 0.53996(15) 0.0498(10) Uani d . 1 . . C C10 0.8770(6) 0.1523(4) 0.57389(15) 0.0535(11) Uani d . 1 . . C C11 0.7376(6) 0.2387(4) 0.57059(15) 0.0549(10) Uani d . 1 . . C C12 0.7341(6) 0.3272(4) 0.53273(14) 0.0499(10) Uani d . 1 . . C C13 0.6642(5) 0.7714(3) 0.30560(14) 0.0453(9) Uani d . 1 . . C C14 0.5921(6) 0.8653(4) 0.33272(17) 0.0543(11) Uani d . 1 . . C C15 0.4532(6) 0.9391(4) 0.30598(18) 0.0633(11) Uani d . 1 . . C C16 0.3963(7) 0.9205(5) 0.2516(2) 0.0661(13) Uani d . 1 . . C C17 0.4712(6) 0.8292(4) 0.22490(17) 0.0576(11) Uani d . 1 . . C C18 0.6053(6) 0.7536(4) 0.25201(16) 0.0536(10) Uani d . 1 . . C C19 1.0604(6) 0.7358(4) 0.28274(17) 0.0607(11) Uani d D 1 . . C C20 1.2069(6) 0.4971(4) 0.32962(18) 0.0627(11) Uani d D 1 . . C H1 1.640(6) 0.135(3) 0.4050(15) 0.065(12) Uiso d . 1 . . H H2 1.237(5) 0.083(4) 0.4624(13) 0.054(10) Uiso d . 1 . . H H3 1.346(6) 0.159(4) 0.5056(18) 0.075(14) Uiso d . 1 . . H H4 1.024(5) 0.393(3) 0.4138(13) 0.035(11) Uiso d . 1 . . H H5 0.758(4) 0.485(3) 0.4632(11) 0.027(8) Uiso d . 1 . . H H6 1.110(5) 0.094(3) 0.5422(13) 0.044(10) Uiso d . 1 . . H H7 0.880(4) 0.089(3) 0.5971(11) 0.024(8) Uiso d . 1 . . H H8 0.641(6) 0.242(4) 0.5956(16) 0.067(11) Uiso d . 1 . . H H9 0.646(6) 0.399(4) 0.5345(14) 0.061(11) Uiso d . 1 . . H H10 0.629(6) 0.877(3) 0.3678(16) 0.062(12) Uiso d . 1 . . H H11 0.402(6) 1.013(4) 0.3332(17) 0.089(14) Uiso d . 1 . . H H12 0.314(6) 0.972(4) 0.2355(17) 0.075(15) Uiso d . 1 . . H H13 0.433(5) 0.814(3) 0.1862(14) 0.041(9) Uiso d . 1 . . H H14 0.665(5) 0.695(4) 0.2313(15) 0.057(11) Uiso d . 1 . . H H15 1.077(6) 0.8163(18) 0.2980(14) 0.109(19) Uiso d D 1 . . H H16 1.015(5) 0.756(3) 0.2458(6) 0.077(13) Uiso d D 1 . . H H17 1.192(3) 0.714(4) 0.2806(16) 0.12(2) Uiso d D 1 . . H H18 1.219(5) 0.478(3) 0.2927(6) 0.086(14) Uiso d D 1 . . H H19 1.330(3) 0.531(3) 0.3419(14) 0.102(17) Uiso d D 1 . . H H20 1.210(6) 0.4192(18) 0.3464(14) 0.113(19) Uiso d D 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 N1 0.0422(17) 0.0525(19) 0.0473(17) 0.0042(14) 0.0140(14) 0.0076(15) N2 0.0440(18) 0.061(2) 0.0452(17) -0.0023(16) 0.0093(14) 0.0048(16) N3 0.0431(19) 0.0453(19) 0.0457(18) 0.0051(16) 0.0087(15) 0.0044(15) N4 0.070(3) 0.061(3) 0.067(2) 0.022(2) 0.019(2) 0.003(2) O1 0.0544(17) 0.0679(19) 0.0617(16) 0.0103(14) 0.0238(14) 0.0161(14) O2 0.0600(19) 0.086(2) 0.079(2) 0.0105(16) 0.0211(16) 0.0222(18) O3 0.063(2) 0.078(2) 0.094(2) 0.0152(17) 0.0290(18) -0.0005(19) O4 0.0485(15) 0.0554(16) 0.0504(14) 0.0042(13) 0.0113(12) 0.0077(12) O5 0.083(3) 0.265(6) 0.109(3) -0.031(4) 0.043(3) -0.016(4) O6 0.414(10) 0.086(3) 0.077(3) -0.010(4) -0.020(4) -0.009(3) O7 0.311(9) 0.243(7) 0.148(4) 0.178(7) 0.134(5) 0.096(4) C1 0.042(2) 0.052(2) 0.0414(19) -0.0026(18) 0.0056(16) 0.0060(18) C2 0.043(2) 0.053(2) 0.0409(19) -0.0040(17) 0.0085(17) 0.0033(18) C3 0.041(2) 0.047(2) 0.0400(19) 0.0034(17) 0.0026(16) -0.0037(17) C4 0.041(2) 0.069(3) 0.052(2) 0.005(2) 0.0041(18) 0.003(2) C5 0.053(3) 0.061(3) 0.059(3) 0.005(2) 0.009(2) 0.006(2) C6 0.048(2) 0.048(2) 0.045(2) 0.0014(19) 0.0083(18) 0.0004(18) C7 0.045(2) 0.044(2) 0.0363(18) -0.0024(17) 0.0030(16) 0.0002(16) C8 0.042(2) 0.053(2) 0.0369(18) -0.0035(17) 0.0067(16) -0.0033(17) C9 0.051(2) 0.051(2) 0.047(2) 0.000(2) 0.0046(19) 0.0005(19) C10 0.069(3) 0.051(2) 0.041(2) -0.005(2) 0.011(2) 0.007(2) C11 0.054(2) 0.064(3) 0.048(2) 0.001(2) 0.0155(19) 0.002(2) C12 0.046(2) 0.058(3) 0.046(2) -0.003(2) 0.0086(18) 0.000(2) C13 0.045(2) 0.045(2) 0.047(2) 0.0003(18) 0.0083(17) 0.0076(18) C14 0.063(3) 0.053(3) 0.045(2) 0.003(2) -0.001(2) 0.007(2) C15 0.068(3) 0.057(3) 0.066(3) 0.006(2) 0.014(2) 0.009(2) C16 0.049(3) 0.068(3) 0.078(3) -0.004(2) -0.003(2) 0.026(3) C17 0.055(3) 0.068(3) 0.049(2) -0.007(2) 0.001(2) 0.008(2) C18 0.056(2) 0.056(3) 0.049(2) -0.003(2) 0.007(2) -0.001(2) C19 0.062(3) 0.067(3) 0.058(3) -0.007(2) 0.025(2) 0.016(2) C20 0.049(3) 0.077(3) 0.065(3) 0.012(2) 0.018(2) 0.005(2) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 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 C1 N1 N2 108.9(3) C1 N1 C13 126.0(3) N2 N1 C13 120.6(3) C3 N2 N1 108.8(3) C3 N2 C19 125.6(3) N1 N2 C19 117.6(3) C6 N3 C2 124.9(3) C6 N3 H4 119(2) C2 N3 H4 117(2) O7 N4 O6 115.4(6) O7 N4 O5 125.2(6) O6 N4 O5 118.7(6) C4 O3 H1 110(2) C8 O4 C5 117.2(3) O1 C1 N1 124.4(3) O1 C1 C2 131.4(3) N1 C1 C2 104.2(3) C3 C2 N3 125.8(3) C3 C2 C1 109.5(3) N3 C2 C1 124.6(3) N2 C3 C2 108.2(3) N2 C3 C20 121.8(3) C2 C3 C20 130.0(4) O2 C4 O3 125.3(4) O2 C4 C5 124.8(4) O3 C4 C5 109.8(4) O4 C5 C4 109.1(4) O4 C5 H2 112(2) C4 C5 H2 112(2) O4 C5 H3 109(3) C4 C5 H3 113(3) H2 C5 H3 101(3) N3 C6 C7 126.8(4) N3 C6 H5 117.7(18) C7 C6 H5 115.2(18) C12 C7 C8 118.4(3) C12 C7 C6 116.5(3) C8 C7 C6 125.2(3) O4 C8 C9 124.5(3) O4 C8 C7 115.9(3) C9 C8 C7 119.5(3) C8 C9 C10 120.2(4) C8 C9 H6 120(2) C10 C9 H6 120(2) C11 C10 C9 120.9(4) C11 C10 H7 122.0(18) C9 C10 H7 117.0(19) C12 C11 C10 119.4(4) C12 C11 H8 118(2) C10 C11 H8 123(2) C11 C12 C7 121.5(4) C11 C12 H9 119(2) C7 C12 H9 119(2) C18 C13 C14 120.7(4) C18 C13 N1 121.5(4) C14 C13 N1 117.8(3) C13 C14 C15 119.5(4) C13 C14 H10 121(3) C15 C14 H10 119(3) C14 C15 C16 119.0(4) C14 C15 H11 113(2) C16 C15 H11 128(2) C17 C16 C15 121.0(5) C17 C16 H12 123(3) C15 C16 H12 116(3) C16 C17 C18 119.9(4) C16 C17 H13 123(2) C18 C17 H13 118(2) C13 C18 C17 119.9(4) C13 C18 H14 122(2) C17 C18 H14 118(2) N2 C19 H15 116(3) N2 C19 H16 121(2) H15 C19 H16 99.7(19) N2 C19 H17 115(3) H15 C19 H17 101(2) H16 C19 H17 102(2) C3 C20 H18 118(2) C3 C20 H19 121(3) H18 C20 H19 102(2) C3 C20 H20 107(3) H18 C20 H20 103(2) H19 C20 H20 104(2) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag N1 C1 . 1.394(4) ? N1 N2 . 1.395(4) ? N1 C13 . 1.426(4) ? N2 C3 . 1.339(4) ? N2 C19 . 1.471(5) ? N3 C6 . 1.304(5) ? N3 C2 . 1.394(5) ? N3 H4 . 0.79(3) ? N4 O7 . 1.103(5) ? N4 O6 . 1.174(6) ? N4 O5 . 1.196(5) ? O1 C1 . 1.240(4) ? O2 C4 . 1.201(5) ? O3 C4 . 1.317(5) ? O3 H1 . 0.96(4) ? O4 C8 . 1.358(4) ? O4 C5 . 1.412(5) ? C1 C2 . 1.422(5) ? C2 C3 . 1.374(5) ? C3 C20 . 1.484(5) ? C4 C5 . 1.510(6) ? C5 H2 . 1.04(4) ? C5 H3 . 0.90(4) ? C6 C7 . 1.433(5) ? C6 H5 . 0.94(3) ? C7 C12 . 1.403(5) ? C7 C8 . 1.417(5) ? C8 C9 . 1.375(5) ? C9 C10 . 1.394(5) ? C9 H6 . 0.94(4) ? C10 C11 . 1.374(6) ? C10 H7 . 0.91(3) ? C11 C12 . 1.367(6) ? C11 H8 . 0.99(4) ? C12 H9 . 1.01(4) ? C13 C18 . 1.373(5) ? C13 C14 . 1.382(5) ? C14 C15 . 1.387(6) ? C14 H10 . 0.90(4) ? C15 C16 . 1.392(6) ? C15 H11 . 1.16(5) ? C16 C17 . 1.362(7) ? C16 H12 . 0.88(5) ? C17 C18 . 1.381(6) ? C17 H13 . 0.99(3) ? C18 H14 . 0.96(4) ? C19 H15 . 0.973(10) ? C19 H16 . 0.970(10) ? C19 H17 . 0.972(10) ? C20 H18 . 0.969(10) ? C20 H19 . 0.965(10) ? C20 H20 . 0.962(10) ? 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 O3 H1 O5 1_655 0.96(4) 1.75(4) 2.567(5) 141(3) N3 H4 O4 . 0.79(3) 2.16(3) 2.724(4) 129(3) 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 C1 N1 N2 C3 -6.0(4) C13 N1 N2 C3 -163.6(3) C1 N1 N2 C19 -156.7(3) C13 N1 N2 C19 45.7(5) N2 N1 C1 O1 -175.1(3) C13 N1 C1 O1 -19.0(6) N2 N1 C1 C2 3.8(4) C13 N1 C1 C2 159.9(3) C6 N3 C2 C3 172.6(4) C6 N3 C2 C1 -5.7(6) O1 C1 C2 C3 178.4(4) N1 C1 C2 C3 -0.4(4) O1 C1 C2 N3 -3.0(6) N1 C1 C2 N3 178.2(3) N1 N2 C3 C2 5.6(4) C19 N2 C3 C2 153.4(4) N1 N2 C3 C20 -174.8(3) C19 N2 C3 C20 -27.0(6) N3 C2 C3 N2 178.1(3) C1 C2 C3 N2 -3.3(4) N3 C2 C3 C20 -1.4(6) C1 C2 C3 C20 177.2(4) C8 O4 C5 C4 -176.3(3) O2 C4 C5 O4 11.4(6) O3 C4 C5 O4 -170.9(3) C2 N3 C6 C7 -179.8(3) N3 C6 C7 C12 -173.4(4) N3 C6 C7 C8 5.7(6) C5 O4 C8 C9 5.5(5) C5 O4 C8 C7 -176.6(3) C12 C7 C8 O4 -175.3(3) C6 C7 C8 O4 5.6(5) C12 C7 C8 C9 2.7(5) C6 C7 C8 C9 -176.4(4) O4 C8 C9 C10 176.5(3) C7 C8 C9 C10 -1.3(5) C8 C9 C10 C11 -0.7(6) C9 C10 C11 C12 1.4(6) C10 C11 C12 C7 0.1(6) C8 C7 C12 C11 -2.1(5) C6 C7 C12 C11 177.1(4) C1 N1 C13 C18 -114.8(4) N2 N1 C13 C18 38.7(5) C1 N1 C13 C14 65.0(5) N2 N1 C13 C14 -141.5(4) C18 C13 C14 C15 2.7(6) N1 C13 C14 C15 -177.1(3) C13 C14 C15 C16 -3.3(6) C14 C15 C16 C17 1.9(6) C15 C16 C17 C18 0.1(7) C14 C13 C18 C17 -0.7(6) N1 C13 C18 C17 179.1(3) C16 C17 C18 C13 -0.7(6)