#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:43:10 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301803 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/07/2200732.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_2200732 loop_ _publ_author_name 'H\"okelek, Tuncer' 'Z\"ulfikaro\(glu, Ay\,sin' 'Bat\?i, H\"umeyra' _publ_section_title ; 1-(2,6-Dimethylphenylamino)propane-1,2-dione dioxime ; _journal_issue 12 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o1247 _journal_page_last o1249 _journal_paper_doi 10.1107/S1600536801020104 _journal_volume 57 _journal_year 2001 _chemical_formula_iupac 'C11 H15 N3 O2' _chemical_formula_moiety 'C11 H15 N3 O2' _chemical_formula_sum 'C11 H15 N3 O2' _chemical_formula_weight 221.26 _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' _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 102.620(19) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 8.404(2) _cell_length_b 7.672(2) _cell_length_c 17.592(3) _cell_measurement_reflns_used 25 _cell_measurement_temperature 296 _cell_measurement_theta_max 18 _cell_measurement_theta_min 10 _cell_volume 1106.8(4) _computing_cell_refinement 'CAD-4 EXPRESS' _computing_data_collection 'CAD-4 EXPRESS (Enraf Nonius, 1994)' _computing_data_reduction 'XCAD4 (Harms & Wocadlo, 1995)' _computing_molecular_graphics 'ORTEP-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX (Farrugia, 1999)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 296 _diffrn_measured_fraction_theta_full 1.00 _diffrn_measured_fraction_theta_max 1.00 _diffrn_measurement_device '\k-geometry diffractometer' _diffrn_measurement_device_type 'Enraf-Nonius Turbo-CAD-4' _diffrn_measurement_method 'non-profiled \w' _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 .0000 _diffrn_reflns_av_sigmaI/netI .0268 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 2198 _diffrn_reflns_theta_full 26.29 _diffrn_reflns_theta_max 26.29 _diffrn_reflns_theta_min 2.37 _diffrn_standards_decay_% 0 _diffrn_standards_interval_time 120 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu .094 _exptl_absorpt_correction_T_max .9861 _exptl_absorpt_correction_T_min .9679 _exptl_absorpt_correction_type refdelf _exptl_absorpt_process_details '(Walker & Stuart, 1983)' _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.328 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 472 _exptl_crystal_size_max .35 _exptl_crystal_size_mid .15 _exptl_crystal_size_min .15 _refine_diff_density_max .374 _refine_diff_density_min -.354 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.133 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 157 _refine_ls_number_reflns 2198 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.133 _refine_ls_R_factor_all .0734 _refine_ls_R_factor_gt .0560 _refine_ls_shift/su_max .001 _refine_ls_shift/su_mean .000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0973P)^2^+0.6954P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .1891 _reflns_number_gt 1769 _reflns_number_total 2198 _reflns_threshold_expression I>2\s(I) _cod_data_source_file ob6096.cif _cod_data_source_block I _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 2200732 _cod_database_fobs_code 2200732 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 H2' -.001(6) .484(5) .257(2) .084(12) Uiso d . 1 . . H H1' .171(4) 1.238(4) .2095(19) .059(9) Uiso d . 1 . . H O2 .0943(2) .4846(2) .23763(11) .0410(5) Uani d . 1 . . O N3 .0955(2) .6571(3) .21243(12) .0350(5) Uani d . 1 . . N O1 .2174(2) 1.1672(2) .18322(12) .0462(5) Uani d . 1 . . O N2 .1935(2) .9994(2) .21332(12) .0353(5) Uani d . 1 . . N N1 .3288(3) .9185(3) .11603(11) .0343(5) Uani d . 1 . . N C2 .1988(3) .7485(3) -.00021(14) .0376(6) Uani d . 1 . . C C9 .2472(3) .8819(3) .17276(13) .0296(5) Uani d . 1 . . C C10 .2328(3) .6975(3) .19670(13) .0305(5) Uani d . 1 . . C C1 .3401(3) .8122(3) .05008(12) .0317(5) Uani d . 1 . . C C6 .4952(3) .7885(3) .03508(14) .0351(5) Uani d . 1 . . C C11 .3747(3) .5792(3) .20340(18) .0469(7) Uani d . 1 . . C H11A .3460 .4633 .2196 .070 Uiso calc R 1 . . H H11B .4669 .6255 .2422 .070 Uiso calc R 1 . . H H11C .4051 .5706 .1528 .070 Uiso calc R 1 . . H C7 .6462(3) .8467(4) .09158(16) .0452(6) Uani d . 1 . . C H7A .6159 .9020 .1366 .068 Uiso calc R 1 . . H H7B .7055 .9305 .0661 .068 Uiso calc R 1 . . H H7C .7159 .7456 .1090 .068 Uiso calc R 1 . . H C3 .2175(4) .6656(4) -.06836(16) .0482(7) Uani d . 1 . . C H3 .1240 .6211 -.1034 .058 Uiso calc R 1 . . H C5 .5062(3) .7056(4) -.03430(15) .0444(6) Uani d . 1 . . C H5 .6101 .6890 -.0463 .053 Uiso calc R 1 . . H C4 .3678(4) .6472(4) -.08579(15) .0502(7) Uani d . 1 . . C H4 .3769 .5942 -.1334 .060 Uiso calc R 1 . . H C8 .0302(3) .7682(4) .01495(17) .0509(7) Uani d . 1 . . C H8A .0368 .8288 .0646 .076 Uiso calc R 1 . . H H8B -.0183 .6528 .0174 .076 Uiso calc R 1 . . H H8C -.0376 .8360 -.0272 .076 Uiso calc R 1 . . H H1 .341(3) 1.021(4) .1108(16) .037(7) Uiso 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 O2 .0473(10) .0298(9) .0525(11) -.0013(7) .0253(9) .0042(7) N3 .0396(11) .0297(10) .0393(11) .0005(8) .0163(9) .0020(8) O1 .0620(12) .0279(9) .0553(11) .0036(8) .0271(10) .0000(8) N2 .0412(11) .0295(11) .0390(11) .0006(8) .0168(9) -.0013(8) N1 .0464(12) .0267(10) .0351(10) -.0032(8) .0202(9) -.0018(8) C2 .0434(13) .0358(13) .0335(12) -.0010(10) .0085(10) .0039(10) C9 .0295(10) .0303(11) .0304(10) .0001(9) .0097(8) -.0009(9) C10 .0353(11) .0292(11) .0296(11) .0005(9) .0126(9) -.0008(9) C1 .0422(12) .0280(11) .0276(11) .0024(9) .0135(9) .0021(8) C6 .0415(13) .0316(12) .0350(12) .0003(10) .0144(10) .0024(9) C11 .0436(14) .0385(14) .0650(17) .0095(11) .0257(13) .0155(12) C7 .0402(14) .0526(16) .0457(14) -.0024(11) .0159(11) .0001(12) C3 .0588(17) .0460(15) .0367(13) -.0038(13) .0039(12) -.0034(12) C5 .0563(16) .0441(15) .0388(13) .0080(12) .0235(12) .0010(11) C4 .0727(19) .0463(16) .0343(13) .0043(14) .0176(13) -.0069(11) C8 .0403(14) .0629(19) .0480(15) -.0055(13) .0062(12) .0027(13) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 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' N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O .0106 .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 _geom_angle_publ_flag N3 O2 H2' 101(3) no C10 N3 O2 111.52(19) yes N2 O1 H1' 105(2) no C9 N2 O1 109.37(18) yes C9 N1 C1 127.5(2) yes C9 N1 H1 113(2) no C1 N1 H1 115(2) no C3 C2 C1 117.5(2) ? C3 C2 C8 119.0(2) ? C1 C2 C8 123.5(2) ? N2 C9 N1 123.8(2) yes N2 C9 C10 116.59(19) yes N1 C9 C10 119.29(19) yes N3 C10 C11 125.6(2) yes N3 C10 C9 115.0(2) yes C11 C10 C9 119.4(2) yes C6 C1 C2 122.1(2) ? C6 C1 N1 117.0(2) ? C2 C1 N1 120.7(2) ? C5 C6 C1 117.8(2) ? C5 C6 C7 120.5(2) ? C1 C6 C7 121.7(2) ? C10 C11 H11A 109.5 ? C10 C11 H11B 109.5 ? H11A C11 H11B 109.5 ? C10 C11 H11C 109.5 ? H11A C11 H11C 109.5 ? H11B C11 H11C 109.5 ? C6 C7 H7A 109.5 ? C6 C7 H7B 109.5 ? H7A C7 H7B 109.5 ? C6 C7 H7C 109.5 ? H7A C7 H7C 109.5 ? H7B C7 H7C 109.5 ? C4 C3 C2 121.4(3) ? C4 C3 H3 119.3 ? C2 C3 H3 119.3 ? C4 C5 C6 120.8(2) ? C4 C5 H5 119.6 ? C6 C5 H5 119.6 ? C3 C4 C5 120.3(2) ? C3 C4 H4 119.9 ? C5 C4 H4 119.9 ? C2 C8 H8A 109.5 ? C2 C8 H8B 109.5 ? H8A C8 H8B 109.5 ? C2 C8 H8C 109.5 ? H8A C8 H8C 109.5 ? H8B C8 H8C 109.5 ? 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 O2 N3 . 1.396(3) yes O2 H2' . .94(5) no N3 C10 . 1.282(3) yes O1 N2 . 1.423(3) yes O1 H1' . .86(3) no N2 C9 . 1.290(3) yes N1 C9 . 1.358(3) yes N1 C1 . 1.438(3) yes N1 H1 . .80(3) no C2 C3 . 1.396(4) ? C2 C1 . 1.404(3) ? C2 C8 . 1.506(4) ? C9 C10 . 1.489(3) yes C10 C11 . 1.482(3) yes C1 C6 . 1.398(3) ? C6 C5 . 1.397(3) ? C6 C7 . 1.498(4) ? C11 H11A . .9800 ? C11 H11B . .9800 ? C11 H11C . .9800 ? C7 H7A . .9800 ? C7 H7B . .9800 ? C7 H7C . .9800 ? C3 C4 . 1.371(4) ? C3 H3 . .9500 ? C5 C4 . 1.383(4) ? C5 H5 . .9500 ? C4 H4 . .9500 ? C8 H8A . .9800 ? C8 H8B . .9800 ? C8 H8C . .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 O1 H1' O2 1_545 .86(4) 2.09(4) 2.889(3) 154(3) yes O2 H2' N2 2_555 .94(3) 1.81(5) 2.742(3) 174(4) yes N1 H1 O1 . .80(3) 2.13(3) 2.53(3) 111(3) yes 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 N2 C9 N1 6.4(3) yes O1 N2 C9 C10 179.61(19) yes C1 N1 C9 N2 -154.7(2) yes C1 N1 C9 C10 32.3(4) yes O2 N3 C10 C11 .2(3) yes O2 N3 C10 C9 -177.37(18) yes N2 C9 C10 N3 44.3(3) ? N1 C9 C10 N3 -142.2(2) ? N2 C9 C10 C11 -133.5(2) ? N1 C9 C10 C11 40.0(3) ? C3 C2 C1 C6 -2.6(3) ? C8 C2 C1 C6 178.7(2) ? C3 C2 C1 N1 171.9(2) ? C8 C2 C1 N1 -6.8(4) ? C9 N1 C1 C6 -132.5(3) ? C9 N1 C1 C2 52.8(3) ? C2 C1 C6 C5 3.0(4) ? N1 C1 C6 C5 -171.7(2) ? C2 C1 C6 C7 -175.9(2) ? N1 C1 C6 C7 9.4(3) ? C1 C2 C3 C4 -.1(4) ? C8 C2 C3 C4 178.7(3) yes C1 C6 C5 C4 -.7(4) ? C7 C6 C5 C4 178.2(2) yes C2 C3 C4 C5 2.3(4) ? C6 C5 C4 C3 -1.9(4) ? loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 30654637 2 PubChem 139065034