#------------------------------------------------------------------------------ #$Date: 2025-08-19 07:12:48 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301798 $ #$URL: svn://www.crystallography.net/cod/cif/2/01/06/2010640.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_2010640 loop_ _publ_author_name 'Moreno-Fuquen, Rodolfo' 'Ribeiro de Castro, Eustaquio Vinicius' 'Moreno, Margarita' 'De Almeida Santos, Regina Helena' 'Monta\~no, Angela Marcela' _publ_section_title ; 1:1 Complex of 4-nitrobenzoic acid and 4-nitropyridine N-oxide ; _journal_issue 2 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 206 _journal_page_last 207 _journal_paper_doi 10.1107/S0108270199013724 _journal_volume 56 _journal_year 2000 _chemical_formula_sum 'C12 H9 N3 O7' _chemical_formula_weight 307.22 _chemical_name_systematic ; 1:1 Complex of 4-nitrobenzoic acid and 4-nitropyridine N-oxide ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _audit_creation_method SHELXL _cell_angle_alpha 90.00 _cell_angle_beta 97.30(2) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 6.2210(10) _cell_length_b 22.2630(10) _cell_length_c 9.4110(10) _cell_measurement_reflns_used 25 _cell_measurement_temperature 293 _cell_measurement_theta_max 18.32 _cell_measurement_theta_min 9.25 _cell_volume 1292.8(3) _computing_cell_refinement 'CAD-4 Software' _computing_data_collection 'CAD-4 Software (Enraf-Nonius 1989)' _computing_data_reduction 'CAD-4 SDP (Frenz, 1978)' _computing_molecular_graphics 'ZORTEP (Zsolnai, 1995)' _computing_publication_material SHELXL93 _computing_structure_refinement SHELXL93 _computing_structure_solution 'SHELXS86 (Sheldrick, 1990)' _diffrn_measurement_device 'Enraf-Nonius CAD-4' _diffrn_measurement_method \w/2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength .71073 _diffrn_reflns_av_R_equivalents .024 _diffrn_reflns_av_sigmaI/netI .050 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_number 2498 _diffrn_reflns_theta_max 24.96 _diffrn_reflns_theta_min 1.83 _diffrn_standards_decay_% 1.52 _diffrn_standards_interval_time 120 _diffrn_standards_number 2 _exptl_absorpt_coefficient_mu .133 _exptl_absorpt_correction_type none _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.578 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 632 _exptl_crystal_size_max .18 _exptl_crystal_size_mid .15 _exptl_crystal_size_min .12 _refine_diff_density_max .189 _refine_diff_density_min -.202 _refine_ls_extinction_coef .178(7) _refine_ls_extinction_method 'SHELXL93 (Sheldrick, 1993)' _refine_ls_goodness_of_fit_all 1.077 _refine_ls_goodness_of_fit_obs 1.033 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 212 _refine_ls_number_reflns 2278 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.095 _refine_ls_restrained_S_obs 1.033 _refine_ls_R_factor_all .094 _refine_ls_R_factor_obs .044 _refine_ls_shift/esd_max <0.001 _refine_ls_shift/esd_mean .000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0379P)^2^+0.7798P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all .132 _refine_ls_wR_factor_obs .094 _reflns_number_observed 1372 _reflns_number_total 2280 _reflns_observed_criterion I>2\s(I) _cod_data_source_file na1431.cif _cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_refine_ls_weighting_scheme' value 'w = 1/[\s^2^(Fo^2^)+(0.0379P)^2^+0.7798P] where P = (Fo^2^+2Fc^2^)/3' was changed to 'calc'. New tag '_refine_ls_weighting_details' was created. The value of the new tag was set to 'w = 1/[\s^2^(Fo^2^)+(0.0379P)^2^+0.7798P] where P = (Fo^2^+2Fc^2^)/3'. Automatic conversion script Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas ; _cod_original_cell_volume 1292.9(3) _cod_original_sg_symbol_H-M 'P 21/n' _cod_original_formula_sum 'C7 H5 N O4 , C5 H4 N2 O3' _cod_database_code 2010640 _cod_database_fobs_code 2010640 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' 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 .0599(15) .071(2) .0641(15) -.0233(13) .0203(11) -.0126(12) O2 .064(2) .098(2) .072(2) -.0256(15) .0055(13) -.0150(15) O3 .070(2) .099(2) .065(2) -.0165(15) .0286(13) .0134(14) N1 .050(2) .0471(15) .0465(15) -.0010(13) .0114(12) -.0003(12) N2 .050(2) .059(2) .056(2) .0007(14) .0095(14) .0102(14) C1 .050(2) .051(2) .040(2) .001(2) .0148(14) -.0035(14) C2 .051(2) .049(2) .040(2) .0022(15) .0077(14) -.0009(14) C3 .045(2) .046(2) .040(2) .0024(14) .0065(13) .0077(13) C4 .056(2) .064(2) .040(2) .000(2) .0189(15) .0012(15) C5 .062(2) .066(2) .043(2) -.009(2) .017(2) -.011(2) O4 .0548(15) .0654(15) .074(2) -.0134(12) .0200(12) -.0077(12) O5 .065(2) .077(2) .063(2) -.0202(14) .0184(12) -.0210(13) O6 .079(2) .079(2) .0584(15) -.0083(14) .0148(13) -.0219(13) O7 .076(2) .080(2) .086(2) -.0317(14) .0300(15) -.0215(14) N3 .052(2) .048(2) .059(2) .0008(13) .0093(14) -.0043(13) C6 .047(2) .046(2) .054(2) .0028(15) .0090(15) -.0005(15) C7 .044(2) .044(2) .045(2) .0033(14) .0062(13) .0065(14) C8 .042(2) .049(2) .052(2) .0031(15) .0154(14) .0066(15) C9 .053(2) .053(2) .042(2) .005(2) .0132(14) -.0013(15) C10 .048(2) .039(2) .045(2) .0017(14) .0081(14) .0012(13) C11 .047(2) .045(2) .050(2) -.0017(15) .0148(14) .0022(14) C12 .053(2) .046(2) .043(2) .002(2) .0128(14) -.0021(14) loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_group _atom_site_type_symbol O1 -.0226(4) .60822(11) .5734(2) .0639(7) Uani d . 1 . O O2 .8064(4) .75937(12) .6781(3) .0783(8) Uani d . 1 . O O3 .8160(4) .73729(12) .4573(3) .0762(8) Uani d . 1 . O N1 .1585(4) .63809(11) .5686(3) .0474(7) Uani d . 1 . N N2 .7328(4) .73510(12) .5671(3) .0547(7) Uani d . 1 . N C1 .2290(5) .67455(13) .6799(3) .0462(7) Uani d . 1 . C H1 .1487 .67819 .7564 .044(8) Uiso calc R 1 . H C2 .4170(5) .70594(14) .6805(3) .0466(8) Uani d . 1 . C H2 .4667 .73062 .7575 .053(9) Uiso calc R 1 . H C3 .5320(5) .70066(13) .5663(3) .0434(7) Uani d . 1 . C C4 .4594(5) .66426(14) .4530(3) .0520(8) Uani d . 1 . C H4 .5370 .66098 .3752 .047(8) Uiso calc R 1 . H C5 .2710(5) .6328(2) .4560(3) .0562(9) Uani d . 1 . C H5 .2205 .6076 .3801 .057(9) Uiso calc R 1 . H O4 -.0131(4) .53401(10) .2338(2) .0638(7) Uani d . 1 . O O5 -.2349(4) .53209(12) .4034(3) .0675(7) Uani d . 1 . O HO5 -.137(7) .561(2) .450(4) .099(14) Uiso d . 1 . H O6 -.7433(4) .34291(11) -.1587(3) .0716(8) Uani d . 1 . O O7 -.9224(4) .33605(12) .0221(3) .0790(8) Uani d . 1 . O N3 -.7714(4) .35524(12) -.0360(3) .0529(7) Uani d . 1 . N C6 -.1754(5) .51581(13) .2789(3) .0489(8) Uani d . 1 . C C7 -.3310(5) .47317(13) .1994(3) .0441(7) Uani d . 1 . C C8 -.2820(5) .44881(13) .0716(3) .0471(8) Uani d . 1 . C H8 -.1525 .45877 .0378 .045(8) Uiso calc R 1 . H C9 -.4250(5) .40987(13) -.0056(3) .0487(8) Uani d . 1 . C H9 -.3927 .39314 -.0910 .049(8) Uiso calc R 1 . H C10 -.6170(5) .39630(13) .0465(3) .0438(7) Uani d . 1 . C C11 -.6704(5) .41954(13) .1731(3) .0466(8) Uani d . 1 . C H11 -.7999 .40925 .2066 .046(8) Uiso calc R 1 . H C12 -.5257(5) .45865(13) .2489(3) .0469(8) Uani d . 1 . C H12 -.5591 .47542 .3340 .050(8) Uiso calc R 1 . H loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source O O .0106 .0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H .0000 .0000 '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 -4 5 0 -9 1 loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle O1 N1 C5 121.0(3) O1 N1 C1 118.2(2) C5 N1 C1 120.8(3) O2 N2 O3 124.1(3) O2 N2 C3 117.8(3) O3 N2 C3 118.1(3) N1 C1 C2 120.3(3) C1 C2 C3 119.1(3) C4 C3 C2 120.6(3) C4 C3 N2 120.7(3) C2 C3 N2 118.7(3) C5 C4 C3 119.1(3) N1 C5 C4 120.2(3) C6 O5 HO5 111(3) O6 N3 O7 123.7(3) O6 N3 C10 118.4(3) O7 N3 C10 117.9(3) O4 C6 O5 123.8(3) O4 C6 C7 123.7(3) O5 C6 C7 112.5(3) C8 C7 C12 119.8(3) C8 C7 C6 119.0(3) C12 C7 C6 121.3(3) C9 C8 C7 120.3(3) C10 C9 C8 118.6(3) C11 C10 C9 122.7(3) C11 C10 N3 118.4(3) C9 C10 N3 118.9(3) C10 C11 C12 118.0(3) C11 C12 C7 120.7(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 . 1.314(3) yes O2 N2 . 1.213(3) ? O3 N2 . 1.214(3) ? N1 C5 . 1.348(4) yes N1 C1 . 1.353(4) yes N2 C3 . 1.465(4) ? C1 C2 . 1.362(4) ? C1 H1 . .93 ? C2 C3 . 1.370(4) ? C2 H2 . .93 ? C3 C4 . 1.369(4) ? C4 C5 . 1.369(4) ? C4 H4 . .93 ? C5 H5 . .93 ? O4 C6 . 1.213(4) ? O5 C6 . 1.324(4) yes O5 HO5 . .95(4) ? O6 N3 . 1.221(3) ? O7 N3 . 1.222(3) ? N3 C10 . 1.474(4) ? C6 C7 . 1.488(4) yes C7 C8 . 1.388(4) ? C7 C12 . 1.390(4) ? C8 C9 . 1.381(4) ? C8 H8 . .93 ? C9 C10 . 1.381(4) ? C9 H9 . .93 ? C10 C11 . 1.378(4) ? C11 C12 . 1.384(4) ? C11 H11 . .93 ? C12 H12 . .93 ? 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 C1 C2 179.3(3) ? C5 N1 C1 C2 -.8(4) ? N1 C1 C2 C3 .8(4) ? C1 C2 C3 C4 -.1(4) ? C1 C2 C3 N2 179.3(3) ? O2 N2 C3 C4 -169.2(3) ? O3 N2 C3 C4 10.3(4) ? O2 N2 C3 C2 11.3(4) yes O3 N2 C3 C2 -169.1(3) ? C2 C3 C4 C5 -.5(5) ? N2 C3 C4 C5 -180.0(3) ? O1 N1 C5 C4 180.0(3) ? C1 N1 C5 C4 .2(5) ? C3 C4 C5 N1 .5(5) ? O4 C6 C7 C8 5.2(5) ? O5 C6 C7 C8 -175.4(3) ? O4 C6 C7 C12 -173.2(3) yes O5 C6 C7 C12 6.2(4) ? C12 C7 C8 C9 -.6(4) ? C6 C7 C8 C9 -179.0(3) ? C7 C8 C9 C10 .5(4) ? C8 C9 C10 C11 -.7(4) ? C8 C9 C10 N3 179.4(3) ? O6 N3 C10 C11 167.5(3) ? O7 N3 C10 C11 -11.6(4) yes O6 N3 C10 C9 -12.7(4) ? O7 N3 C10 C9 168.3(3) ? C9 C10 C11 C12 .9(4) ? N3 C10 C11 C12 -179.2(3) ? C10 C11 C12 C7 -1.0(4) ? C8 C7 C12 C11 .8(4) ? C6 C7 C12 C11 179.2(3) ? loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 21107171 2 PubChem 139057565