#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:43:10 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301803 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/08/2200803.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_2200803 loop_ _publ_author_name 'Yatsenko, Alexandr V.' 'Paseshnichenko, Ksenia A.' 'Chernyshev, Vladimir V.' 'Schenk, Henk' _publ_section_title ; 1-[(2-Nitrophenyl)hydrazono]-1H-naphthalen-2-one (Pigment Orange 2) from powder data ; _journal_issue 12 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o1152 _journal_page_last o1153 _journal_paper_doi 10.1107/S1600536801018268 _journal_volume 57 _journal_year 2001 _chemical_formula_sum 'C16 H11 N3 O3' _chemical_formula_weight 293.28 _chemical_melting_point 487 _chemical_name_common 'Pigment Orange 2' _chemical_name_systematic ; 1-[(2-nitrophenyl)hydrazono]-1H-naphthalen-2-one ; _space_group_IT_number 19 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_space_group_name_H-M 'P 21 21 21' _cell_angle_alpha 90.0 _cell_angle_beta 90.0 _cell_angle_gamma 90.0 _cell_formula_units_Z 4 _cell_length_a 15.036(5) _cell_length_b 12.722(4) _cell_length_c 7.042(3) _cell_measurement_reflns_used 46 _cell_measurement_temperature 295(2) _cell_measurement_theta_max 25.9 _cell_measurement_theta_min 4.1 _cell_volume 1347.1(8) _computing_cell_refinement 'LSPAID (Visser, 1986)' _computing_data_collection 'local program' _computing_molecular_graphics 'PLUTON (Spek, 1992)' _computing_publication_material 'PARST (Nardelli, 1983)' _computing_structure_refinement MRIA _computing_structure_solution 'MRIA (Zlokazov & Chernyshev, 1992)' _diffrn_ambient_temperature 295(2) _diffrn_measurement_device_type ' DRON-3M diffractometer (Burevestnik, Russia)' _diffrn_radiation_monochromator 'Ni filtered' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.5418 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 4 _diffrn_reflns_limit_l_min 0 _exptl_absorpt_coefficient_mu .85 _exptl_absorpt_correction_type none _exptl_crystal_density_diffrn 1.446 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 608 _refine_diff_density_max .55 _refine_diff_density_min -.50 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_all 3.86 _refine_ls_hydrogen_treatment noref _refine_ls_matrix_type fullcycle _refine_ls_number_constraints 0 _refine_ls_number_parameters 112 _refine_ls_number_restraints 14 _refine_ls_shift/su_max .042 _refine_ls_shift/su_mean .010 _refine_ls_structure_factor_coef Inet _refine_ls_weighting_scheme sigma _cod_data_source_file ya6065.cif _cod_data_source_block I _cod_database_code 2200803 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '1/2+x, 1/2-y, -z' '-x, 1/2+y, 1/2-z' '1/2-x, -y, 1/2+z' 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_occupancy _atom_site_type_symbol O1 .1068(3) .5962(4) .1680(7) .094(2) Uiso 1 O O2 .2187(3) .7735(4) .0969(11) .110(2) Uiso 1 O O3 .3150(4) .8961(3) .0785(11) .110(2) Uiso 1 O N1 .2717(3) .5780(4) .1271(9) .062(2) Uiso 1 N N2 .2677(4) .4717(5) .1146(7) .062(2) Uiso 1 N N3 .2957(3) .8031(3) .0932(9) .110(2) Uiso 1 N C1 .1843(3) .4366(3) .1272(5) .094(2) Uiso 1 C C2 .1008(3) .4962(3) .1551(8) .094(2) Uiso 1 C C3 .0164(3) .4387(3) .1684(9) .094(2) Uiso 1 C C4 .0131(3) .3350(3) .1522(7) .094(2) Uiso 1 C C5 .0869(3) .1652(4) .1082(9) .094(2) Uiso 1 C C6 .1625(3) .1050(3) .0817(6) .094(2) Uiso 1 C C7 .2468(3) .1537(3) .0677(8) .094(2) Uiso 1 C C8 .2547(3) .2622(3) .0827(8) .094(2) Uiso 1 C C9 .1782(3) .3231(3) .1123(8) .094(2) Uiso 1 C C10 .0937(3) .2751(3) .1226(7) .094(2) Uiso 1 C C11 .3558(3) .6169(4) .1309(9) .062(2) Uiso 1 C C12 .3693(3) .7258(4) .1181(7) .062(2) Uiso 1 C C13 .4559(3) .7671(3) .1258(10) .062(2) Uiso 1 C C14 .5279(3) .7012(3) .1426(8) .062(2) Uiso 1 C C15 .5144(3) .5924(3) .1549(10) .062(2) Uiso 1 C C16 .4299(3) .5506(3) .1550(9) .062(2) Uiso 1 C H1 .2236 .6186 .1447 .074 Uiso 1 H H3 -.0336 .4839 .1867 .11 Uiso 1 H H4 -.0398 .2933 .1590 .11 Uiso 1 H H5 .0300 .1335 .1182 .11 Uiso 1 H H6 .1593 .0308 .0718 .11 Uiso 1 H H7 .2974 .1108 .0494 .11 Uiso 1 H H8 .3109 .2955 .0750 .11 Uiso 1 H H13 .4635 .8411 .1129 .074 Uiso 1 H H14 .5870 .7280 .1437 .074 Uiso 1 H H15 .5650 .5479 .1703 .074 Uiso 1 H H16 .4200 .4772 .1688 .074 Uiso 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 .047 .032 'International Tables for X-Ray Crystallography (Vol. IV)' N N .029 .018 'International Tables for X-Ray Crystallography (Vol. IV)' C C .017 .009 'International Tables for X-Ray Crystallography (Vol. IV)' H H .000 .000 'International Tables for X-Ray Crystallography (Vol. IV)' 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 N2 N1 C11 113.9(5) no N1 N2 C1 111.8(5) no O2 N3 O3 121.8(5) no O3 N3 C12 118.2(4) no O2 N3 C12 120.0(4) no N2 C1 C9 112.8(4) no N2 C1 C2 129.4(5) no C2 C1 C9 117.8(3) no O1 C2 C1 117.4(4) no C1 C2 C3 119.1(4) no O1 C2 C3 123.5(4) no C2 C3 C4 121.5(4) no C3 C4 C10 120.4(4) no C6 C5 C10 120.1(4) no C5 C6 C7 120.2(4) no C6 C7 C8 120.4(4) no C7 C8 C9 119.3(4) no C1 C9 C8 120.6(4) no C8 C9 C10 120.5(4) no C1 C9 C10 118.9(4) no C5 C10 C9 119.5(4) no C4 C10 C9 122.3(4) no C4 C10 C5 118.3(4) no N1 C11 C16 121.4(4) no N1 C11 C12 119.6(5) no C12 C11 C16 119.0(4) no N3 C12 C11 123.5(4) no C11 C12 C13 120.1(4) no N3 C12 C13 116.5(4) no C12 C13 C14 120.3(4) no C13 C14 C15 119.6(4) no C14 C15 C16 121.0(4) no C11 C16 C15 119.9(4) no C11 N1 H1 122.5 no N2 N1 H1 123.2 no C2 C3 H3 112.9 no C4 C3 H3 125.6 no C3 C4 H4 125.4 no C10 C4 H4 114.3 no C10 C5 H5 118.9 no C6 C5 H5 121.1 no C7 C6 H6 118.5 no C5 C6 H6 121.3 no C8 C7 H7 121.0 no C6 C7 H7 118.6 no C7 C8 H8 121.1 no C9 C8 H8 119.6 no C12 C13 H13 118.5 no C14 C13 H13 121.1 no C13 C14 H14 121.2 no C15 C14 H14 119.2 no C14 C15 H15 118.5 no C16 C15 H15 120.4 no C15 C16 H16 121.6 no C11 C16 H16 118.5 no 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 C2 . 1.279(6) no O2 N3 . 1.218(6) no O3 N3 . 1.223(6) no N1 N2 . 1.357(8) no N1 C11 . 1.358(7) no N2 C1 . 1.334(8) no N3 C12 . 1.491(6) no C1 C2 . 1.480(6) no C1 C9 . 1.451(5) no C2 C3 . 1.468(6) no C3 C4 . 1.325(5) no C4 C10 . 1.447(6) no C5 C6 . 1.383(6) no C5 C10 . 1.406(6) no C6 C7 . 1.414(6) no C7 C8 . 1.390(5) no C8 C9 . 1.402(6) no C9 C10 . 1.412(6) no C11 C12 . 1.403(7) no C11 C16 . 1.408(6) no C12 C13 . 1.405(6) no C13 C14 . 1.374(6) no C14 C15 . 1.402(6) no C15 C16 . 1.377(6) no N1 H1 . .897 no C3 H3 . .955 no C4 H4 . .957 no C5 H5 . .949 no C6 H6 . .948 no C7 H7 . .945 no C8 H8 . .947 no C13 H13 . .953 no C14 H14 . .952 no C15 H15 . .955 no C16 H16 . .951 no loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 4588175 2 PubChem 80852