#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:43:10 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301803 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/67/2206713.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_2206713 loop_ _publ_author_name 'Moreno-Fuquen, Rodolfo' 'Monta\~no, Angela Marcela' 'Atencio, Reinaldo' _publ_section_title ; Isoquinoline 1-oxide--2-nitrobenzoic acid (1/1) ; _journal_coeditor_code HG6230 _journal_issue 9 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o3061 _journal_page_last o3062 _journal_paper_doi 10.1107/S1600536805026334 _journal_volume 61 _journal_year 2005 _chemical_formula_iupac 'C9 H7 N O, C7 H5 N O4' _chemical_formula_moiety 'C9 H7 N O, C7 H5 N O4' _chemical_formula_sum 'C16 H12 N2 O5' _chemical_formula_weight 312.28 _chemical_melting_point 387.0(10) _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 96.399(18) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 11.639(3) _cell_length_b 7.235(4) _cell_length_c 17.206(3) _cell_measurement_reflns_used 25 _cell_measurement_temperature 293 _cell_measurement_theta_max 25.03 _cell_measurement_theta_min 1.0 _cell_volume 1439.9(9) _computing_cell_refinement 'MSC/AFC Diffractometer Control Software' _computing_data_collection ; MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1993) ; _computing_data_reduction 'TEXSAN (Molecular Structure Corporation, 1995)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS86 (Sheldrick, 1990)' _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.996 _diffrn_measurement_device_type 'Rigaku AFC-7S' _diffrn_measurement_method \w/2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus X-ray sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_sigmaI/netI 0.0246 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_number 2532 _diffrn_reflns_theta_full 25.03 _diffrn_reflns_theta_max 25.03 _diffrn_reflns_theta_min 1.76 _diffrn_standards_decay_% 0 _diffrn_standards_interval_time 150 _diffrn_standards_number 2 _exptl_absorpt_coefficient_mu 0.109 _exptl_absorpt_correction_type none _exptl_crystal_colour pale-yellow _exptl_crystal_density_diffrn 1.441 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 648 _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.12 _refine_diff_density_max 0.184 _refine_diff_density_min -0.164 _refine_ls_extinction_coef 0.0214(15) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL97 _refine_ls_goodness_of_fit_ref 1.083 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 213 _refine_ls_number_reflns 2532 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.083 _refine_ls_R_factor_all 0.067 _refine_ls_R_factor_gt 0.040 _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^)+(0.0367P)^2^+0.6379P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.086 _refine_ls_wR_factor_ref 0.104 _reflns_number_gt 1847 _reflns_number_total 2532 _reflns_threshold_expression I>2\s(I) _cod_data_source_file hg6230.cif _cod_data_source_block I _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 2206713 _cod_database_fobs_code 2206713 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 O1 0.40744(12) 0.1866(2) 0.22580(8) 0.0465(4) Uani d . 1 O N1 0.48582(14) 0.1614(2) 0.17589(10) 0.0367(4) Uani d . 1 N C8 0.49669(17) -0.0030(3) 0.14362(12) 0.0380(5) Uani d . 1 C H8 0.4485 -0.0990 0.1556 0.046 Uiso calc R 1 H C9 0.57919(17) -0.0354(3) 0.09174(11) 0.0359(5) Uani d . 1 C C16 0.55663(17) 0.3065(3) 0.16014(12) 0.0420(5) Uani d . 1 C H16 0.5485 0.4208 0.1836 0.050 Uiso calc R 1 H C14 0.65181(17) 0.1123(3) 0.07356(12) 0.0386(5) Uani d . 1 C C15 0.63738(18) 0.2825(3) 0.11095(13) 0.0430(5) Uani d . 1 C H15 0.6851 0.3811 0.1014 0.052 Uiso calc R 1 H C10 0.58902(19) -0.2097(3) 0.05616(13) 0.0455(5) Uani d . 1 C H10 0.5420 -0.3072 0.0681 0.055 Uiso calc R 1 H C13 0.73171(18) 0.0807(3) 0.01953(13) 0.0489(6) Uani d . 1 C H13 0.7800 0.1758 0.0068 0.059 Uiso calc R 1 H C12 0.7387(2) -0.0885(4) -0.01425(14) 0.0548(6) Uani d . 1 C H12 0.7916 -0.1075 -0.0502 0.066 Uiso calc R 1 H C11 0.6677(2) -0.2342(3) 0.00431(13) 0.0522(6) Uani d . 1 C H11 0.6744 -0.3491 -0.0191 0.063 Uiso calc R 1 H O4 0.24361(14) 0.4142(2) 0.20581(11) 0.0579(5) Uani d . 1 O HO4 0.315(3) 0.330(5) 0.2080(19) 0.109(12) Uiso d . 1 H N2 0.01858(18) 0.4717(3) 0.10164(12) 0.0547(5) Uani d . 1 N C2 0.04442(18) 0.6520(3) 0.13718(12) 0.0399(5) Uani d . 1 C C1 0.15747(17) 0.6985(3) 0.16543(12) 0.0373(5) Uani d . 1 C C7 0.25856(17) 0.5686(3) 0.16991(13) 0.0413(5) Uani d . 1 C C6 0.17605(19) 0.8761(3) 0.19298(13) 0.0454(6) Uani d . 1 C H6 0.2506 0.9122 0.2120 0.054 Uiso calc R 1 H C5 0.0867(2) 1.0021(3) 0.19299(14) 0.0518(6) Uani d . 1 C H5 0.1016 1.1215 0.2114 0.062 Uiso calc R 1 H C4 -0.0242(2) 0.9506(3) 0.16577(15) 0.0554(6) Uani d . 1 C H4 -0.0846 1.0346 0.1664 0.066 Uiso calc R 1 H C3 -0.04582(19) 0.7751(3) 0.13765(14) 0.0508(6) Uani d . 1 C H3 -0.1207 0.7396 0.1191 0.061 Uiso calc R 1 H O5 0.34724(14) 0.6113(2) 0.14451(13) 0.0738(6) Uani d . 1 O O2 0.08988(17) 0.4029(3) 0.06384(12) 0.0775(6) Uani d . 1 O O3 -0.07481(17) 0.4013(3) 0.10961(14) 0.0884(7) 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 O1 0.0473(8) 0.0438(9) 0.0507(9) 0.0115(7) 0.0158(7) 0.0054(7) N1 0.0353(9) 0.0337(10) 0.0405(9) 0.0034(7) 0.0022(8) 0.0010(8) C8 0.0371(11) 0.0323(11) 0.0437(12) -0.0013(9) 0.0006(9) 0.0041(10) C9 0.0340(10) 0.0349(11) 0.0371(11) 0.0031(9) -0.0033(9) 0.0037(9) C16 0.0438(12) 0.0312(11) 0.0495(13) -0.0020(10) -0.0006(10) -0.0045(10) C14 0.0343(11) 0.0374(12) 0.0430(11) 0.0011(9) -0.0011(9) 0.0037(10) C15 0.0395(11) 0.0365(12) 0.0522(13) -0.0067(10) 0.0018(10) 0.0028(10) C10 0.0500(13) 0.0346(12) 0.0506(13) 0.0021(10) -0.0002(11) -0.0014(10) C13 0.0390(12) 0.0537(15) 0.0548(14) 0.0013(11) 0.0088(10) 0.0084(12) C12 0.0531(14) 0.0635(17) 0.0493(13) 0.0171(13) 0.0130(11) 0.0048(13) C11 0.0623(15) 0.0445(13) 0.0488(13) 0.0148(12) 0.0024(12) -0.0050(11) O4 0.0437(9) 0.0492(10) 0.0831(12) 0.0100(8) 0.0178(8) 0.0239(9) N2 0.0501(12) 0.0435(12) 0.0669(14) -0.0001(10) -0.0104(10) -0.0021(10) C2 0.0399(11) 0.0363(12) 0.0428(12) -0.0004(9) 0.0012(9) 0.0037(10) C1 0.0352(11) 0.0352(11) 0.0425(11) -0.0005(9) 0.0080(9) 0.0054(10) C7 0.0349(11) 0.0383(12) 0.0504(13) -0.0023(10) 0.0040(10) 0.0000(10) C6 0.0404(12) 0.0398(13) 0.0558(14) -0.0038(10) 0.0053(10) -0.0014(11) C5 0.0620(15) 0.0373(12) 0.0575(14) 0.0023(12) 0.0135(12) -0.0037(11) C4 0.0536(14) 0.0469(15) 0.0670(16) 0.0150(12) 0.0122(12) 0.0072(12) C3 0.0380(12) 0.0495(14) 0.0633(15) 0.0049(11) -0.0013(11) 0.0071(12) O5 0.0439(10) 0.0509(11) 0.1322(17) 0.0026(8) 0.0348(11) 0.0183(11) O2 0.0697(12) 0.0662(13) 0.0938(14) 0.0141(10) -0.0032(11) -0.0316(11) O3 0.0646(12) 0.0676(14) 0.1300(18) -0.0276(11) -0.0027(12) -0.0100(13) 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_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 1 0 2 0 1 1 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 C8 N1 O1 119.79(17) ? C8 N1 C16 120.90(18) ? O1 N1 C16 119.29(17) yes N1 C8 C9 121.42(19) ? N1 C8 H8 119.3 ? C9 C8 H8 119.3 ? C8 C9 C10 121.31(19) ? C8 C9 C14 118.79(19) ? C10 C9 C14 119.9(2) ? C15 C16 N1 120.0(2) ? C15 C16 H16 120.0 ? N1 C16 H16 120.0 ? C13 C14 C15 124.5(2) ? C13 C14 C9 118.5(2) ? C15 C14 C9 116.97(19) ? C16 C15 C14 121.9(2) ? C16 C15 H15 119.1 ? C14 C15 H15 119.1 ? C11 C10 C9 119.6(2) ? C11 C10 H10 120.2 ? C9 C10 H10 120.2 ? C12 C13 C14 120.3(2) ? C12 C13 H13 119.8 ? C14 C13 H13 119.8 ? C13 C12 C11 121.0(2) ? C13 C12 H12 119.5 ? C11 C12 H12 119.5 ? C10 C11 C12 120.7(2) ? C10 C11 H11 119.7 ? C12 C11 H11 119.7 ? C7 O4 HO4 112.4(18) ? O2 N2 O3 123.9(2) yes O2 N2 C2 118.0(2) yes O3 N2 C2 118.1(2) ? C3 C2 C1 122.2(2) ? C3 C2 N2 117.33(19) ? C1 C2 N2 120.36(19) ? C6 C1 C2 116.82(19) ? C6 C1 C7 118.30(19) ? C2 C1 C7 124.86(19) ? O5 C7 O4 124.0(2) ? O5 C7 C1 121.3(2) ? O4 C7 C1 114.67(18) ? C1 C6 C5 121.7(2) ? C1 C6 H6 119.2 ? C5 C6 H6 119.2 ? C4 C5 C6 119.9(2) ? C4 C5 H5 120.0 ? C6 C5 H5 120.0 ? C3 C4 C5 120.0(2) ? C3 C4 H4 120.0 ? C5 C4 H4 120.0 ? C4 C3 C2 119.4(2) ? C4 C3 H3 120.3 ? C2 C3 H3 120.3 ? 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 O1 N1 . 1.333(2) yes N1 C8 . 1.325(3) yes N1 C16 . 1.380(3) yes C8 C9 . 1.402(3) ? C8 H8 . 0.9300 ? C9 C10 . 1.412(3) ? C9 C14 . 1.419(3) ? C16 C15 . 1.344(3) ? C16 H16 . 0.9300 ? C14 C13 . 1.405(3) ? C14 C15 . 1.408(3) ? C15 H15 . 0.9300 ? C10 C11 . 1.359(3) ? C10 H10 . 0.9300 ? C13 C12 . 1.361(3) ? C13 H13 . 0.9300 ? C12 C11 . 1.399(3) ? C12 H12 . 0.9300 ? C11 H11 . 0.9300 ? O4 C7 . 1.297(3) ? O4 HO4 . 1.03(3) yes N2 O2 . 1.216(2) yes N2 O3 . 1.222(3) yes N2 C2 . 1.458(3) yes C2 C3 . 1.378(3) ? C2 C1 . 1.392(3) ? C1 C6 . 1.378(3) ? C1 C7 . 1.501(3) yes C7 O5 . 1.205(2) yes C7 O4 1 1.297(3) yes C6 C5 . 1.383(3) ? C6 H6 . 0.9300 ? C5 C4 . 1.374(3) ? C5 H5 . 0.9300 ? C4 C3 . 1.372(3) ? C4 H4 . 0.9300 ? C3 H3 . 0.9300 ? 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 O1 N1 C8 C9 -179.10(17) ? C16 N1 C8 C9 -0.8(3) ? N1 C8 C9 C10 -178.69(19) ? N1 C8 C9 C14 -0.3(3) ? C8 N1 C16 C15 0.6(3) ? O1 N1 C16 C15 178.91(18) ? C8 C9 C14 C13 -177.91(18) ? C10 C9 C14 C13 0.5(3) ? C8 C9 C14 C15 1.5(3) ? C10 C9 C14 C15 179.88(19) ? N1 C16 C15 C14 0.7(3) ? C13 C14 C15 C16 177.6(2) ? C9 C14 C15 C16 -1.7(3) ? C8 C9 C10 C11 178.0(2) ? C14 C9 C10 C11 -0.4(3) ? C15 C14 C13 C12 -179.4(2) ? C9 C14 C13 C12 -0.1(3) ? C14 C13 C12 C11 -0.5(3) ? C9 C10 C11 C12 -0.1(3) ? C13 C12 C11 C10 0.6(4) ? O2 N2 C2 C3 142.0(2) ? O3 N2 C2 C3 -35.8(3) yes O2 N2 C2 C1 -34.7(3) ? O3 N2 C2 C1 147.4(2) ? C3 C2 C1 C6 -1.2(3) ? N2 C2 C1 C6 175.42(19) ? C3 C2 C1 C7 177.1(2) ? N2 C2 C1 C7 -6.3(3) ? C6 C1 C7 O5 -51.5(3) yes C2 C1 C7 O5 130.2(2) yes C6 C1 C7 O4 125.5(2) ? C2 C1 C7 O4 -52.7(3) ? C2 C1 C6 C5 0.3(3) ? C7 C1 C6 C5 -178.0(2) ? C1 C6 C5 C4 0.7(4) ? C6 C5 C4 C3 -0.9(4) ? C5 C4 C3 C2 0.1(4) ? C1 C2 C3 C4 0.9(3) ? N2 C2 C3 C4 -175.7(2) ? loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 71412897