#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:43:10 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301803 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/69/2206922.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_2206922 loop_ _publ_author_name 'Alpaslan, G\"okhan' '\"Ozdamar, \"Ozg\"ur' 'Odaba\,soglu, Mustafa' 'Ersanl\?i, Cem C\"uneyt' 'Erd\"onmez, Ahmet' 'Ocak \'Iskeleli, Nazan' _publ_section_title ; (Z)-Ethyl 4-chloro-2-[2-(2-methoxyphenyl)hydrazono]-3-oxobutanoate ; _journal_issue 10 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o3442 _journal_page_last o3444 _journal_paper_doi 10.1107/S1600536805030163 _journal_volume 61 _journal_year 2005 _chemical_formula_iupac 'C13 H15 Cl N2 O4' _chemical_formula_moiety 'C13 H15 Cl N2 O4' _chemical_formula_sum 'C13 H15 Cl N2 O4' _chemical_formula_weight 298.72 _chemical_name_systematic ; (Z)-ethyl 4-chloro-2-(2-(2-methoxyphenyl)hydrazono)-3-oxobutanoate ; _space_group_IT_number 2 _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 107.615(5) _cell_angle_beta 103.543(5) _cell_angle_gamma 94.952(5) _cell_formula_units_Z 2 _cell_length_a 8.605(5) _cell_length_b 8.981(5) _cell_length_c 9.974(5) _cell_measurement_reflns_used 8830 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 27.2 _cell_measurement_theta_min 2.4 _cell_volume 703.9(7) _computing_cell_refinement X-AREA _computing_data_collection 'X-AREA (Stoe & Cie, 2002)' _computing_data_reduction 'X-RED32 (Stoe & Cie, 2002)' _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, 1990)' _diffrn_ambient_temperature 296(2) _diffrn_detector_area_resol_mean 6.67 _diffrn_measured_fraction_theta_full 1.00 _diffrn_measured_fraction_theta_max 1.00 _diffrn_measurement_device_type 'STOE IPDS-II' _diffrn_measurement_method w _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71069 _diffrn_reflns_av_R_equivalents 0.027 _diffrn_reflns_av_sigmaI/netI 0.025 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 10993 _diffrn_reflns_theta_full 26.0 _diffrn_reflns_theta_max 26.0 _diffrn_reflns_theta_min 2.4 _diffrn_standards_decay_% 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.286 _exptl_absorpt_correction_T_max 0.964 _exptl_absorpt_correction_T_min 0.885 _exptl_absorpt_correction_type integration _exptl_absorpt_process_details '(X-RED32; Stoe & Cie, 2002)' _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.409 _exptl_crystal_density_method 'not measured' _exptl_crystal_description Prism _exptl_crystal_F_000 312 _exptl_crystal_size_max 0.49 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.14 _refine_diff_density_max 0.15 _refine_diff_density_min -0.18 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.03 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 187 _refine_ls_number_reflns 2741 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.03 _refine_ls_R_factor_all 0.062 _refine_ls_R_factor_gt 0.040 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean <0.001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0645P)^2^+0.0281P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.107 _refine_ls_wR_factor_ref 0.117 _reflns_number_gt 1906 _reflns_number_total 2741 _reflns_threshold_expression 'I >2\s(I)' _cod_data_source_file ci6657.cif _cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic' 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 'Triclinic' changed to 'triclinic' 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_database_code 2206922 _cod_database_fobs_code 2206922 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -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_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_type_symbol C1 0.1950(2) 0.5853(2) 0.4889(2) 0.0594(5) Uani d . 1 C C2 0.1743(3) 0.7305(3) 0.5723(2) 0.0744(6) Uani d . 1 C H2 0.2404 0.7782 0.6673 0.089 Uiso calc R 1 H C3 0.0556(3) 0.8064(3) 0.5156(3) 0.0921(7) Uani d . 1 C H3 0.0405 0.9043 0.5725 0.110 Uiso calc R 1 H C4 -0.0399(3) 0.7356(4) 0.3742(4) 0.0964(9) Uani d . 1 C H4 -0.1204 0.7861 0.3361 0.116 Uiso calc R 1 H C5 -0.0184(3) 0.5927(4) 0.2894(3) 0.0833(7) Uani d . 1 C H5 -0.0828 0.5474 0.1935 0.100 Uiso calc R 1 H C6 0.0993(2) 0.5143(3) 0.3454(2) 0.0655(5) Uani d . 1 C C7 0.0222(3) 0.2850(4) 0.1324(2) 0.0999(8) Uani d . 1 C H7A -0.0867 0.2728 0.1408 0.120 Uiso calc R 1 H H7B 0.0507 0.1824 0.0953 0.120 Uiso calc R 1 H H7C 0.0293 0.3426 0.0665 0.120 Uiso calc R 1 H C8 0.4985(2) 0.4883(2) 0.74401(18) 0.0521(4) Uani d . 1 C C9 0.5891(2) 0.5861(2) 0.89488(19) 0.0554(4) Uani d . 1 C C10 0.5456(3) 0.7501(2) 0.9452(2) 0.0768(6) Uani d . 1 C H10A 0.4391 0.7408 0.9618 0.092 Uiso calc R 1 H H10B 0.5400 0.7961 0.8682 0.092 Uiso calc R 1 H C11 0.5138(2) 0.3230(2) 0.67202(19) 0.0568(4) Uani d . 1 C C12 0.6319(3) 0.1000(2) 0.6823(2) 0.0728(6) Uani d . 1 C H12A 0.6634 0.0902 0.5931 0.087 Uiso calc R 1 H H12B 0.5289 0.0308 0.6572 0.087 Uiso calc R 1 H C13 0.7580(3) 0.0549(3) 0.7864(3) 0.0876(7) Uani d . 1 C H13A 0.8588 0.1253 0.8119 0.105 Uiso calc R 1 H H13B 0.7719 -0.0519 0.7413 0.105 Uiso calc R 1 H H13C 0.7243 0.0623 0.8731 0.105 Uiso calc R 1 H N1 0.30838(19) 0.5002(2) 0.54512(17) 0.0570(4) Uani d . 1 N N2 0.39947(17) 0.56386(17) 0.67872(15) 0.0536(4) Uani d . 1 N O1 0.43650(18) 0.24860(17) 0.54691(14) 0.0750(4) Uani d . 1 O O2 0.61716(17) 0.26297(15) 0.75319(13) 0.0645(4) Uani d . 1 O O3 0.68687(18) 0.54210(16) 0.97574(14) 0.0745(4) Uani d . 1 O O4 0.13042(18) 0.3696(2) 0.27202(15) 0.0792(4) Uani d . 1 O Cl1 0.68642(8) 0.87846(7) 1.10700(6) 0.0881(2) Uani d . 1 Cl H1 0.307(3) 0.412(3) 0.499(3) 0.074(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 C1 0.0548(10) 0.0677(12) 0.0561(10) 0.0082(9) 0.0013(8) 0.0322(9) C2 0.0797(14) 0.0692(13) 0.0743(13) 0.0188(11) 0.0049(11) 0.0345(11) C3 0.0944(17) 0.0855(17) 0.1098(19) 0.0348(14) 0.0165(15) 0.0550(16) C4 0.0746(15) 0.113(2) 0.120(2) 0.0290(15) 0.0056(15) 0.077(2) C5 0.0612(12) 0.117(2) 0.0773(14) 0.0083(13) -0.0049(11) 0.0605(16) C6 0.0543(11) 0.0858(15) 0.0559(11) 0.0069(10) 0.0002(9) 0.0357(11) C7 0.0833(16) 0.132(2) 0.0541(12) 0.0032(15) -0.0121(11) 0.0154(13) C8 0.0550(10) 0.0515(10) 0.0448(8) 0.0088(8) 0.0018(7) 0.0180(7) C9 0.0594(10) 0.0522(10) 0.0473(9) 0.0079(8) 0.0005(8) 0.0176(8) C10 0.0890(15) 0.0580(11) 0.0575(11) 0.0137(10) -0.0155(10) 0.0089(9) C11 0.0562(10) 0.0590(11) 0.0493(9) 0.0110(9) 0.0043(8) 0.0172(8) C12 0.0932(15) 0.0572(11) 0.0577(11) 0.0294(11) 0.0055(10) 0.0116(9) C13 0.1139(19) 0.0707(14) 0.0689(14) 0.0370(14) 0.0027(13) 0.0210(11) N1 0.0586(9) 0.0589(10) 0.0445(8) 0.0112(8) -0.0041(7) 0.0178(7) N2 0.0542(8) 0.0565(8) 0.0437(7) 0.0071(7) -0.0008(6) 0.0190(6) O1 0.0829(9) 0.0651(8) 0.0530(8) 0.0236(7) -0.0093(7) 0.0038(6) O2 0.0781(9) 0.0546(7) 0.0503(7) 0.0203(6) -0.0010(6) 0.0140(6) O3 0.0829(9) 0.0653(8) 0.0560(7) 0.0185(7) -0.0161(7) 0.0177(6) O4 0.0683(9) 0.1021(12) 0.0498(7) 0.0104(8) -0.0073(6) 0.0196(8) Cl1 0.1087(5) 0.0644(3) 0.0593(3) 0.0090(3) -0.0121(3) 0.0034(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' Cl Cl 0.1484 0.1585 '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 C2 C1 C6 120.45(19) ? C2 C1 N1 121.94(18) ? C6 C1 N1 117.6(2) ? C1 C2 C3 120.2(2) ? C1 C2 H2 119.9 ? C3 C2 H2 119.9 ? C4 C3 C2 119.4(3) ? C4 C3 H3 120.3 ? C2 C3 H3 120.3 ? C5 C4 C3 120.9(2) ? C5 C4 H4 119.5 ? C3 C4 H4 119.5 ? C4 C5 C6 120.3(2) ? C4 C5 H5 119.8 ? C6 C5 H5 119.8 ? O4 C6 C5 125.7(2) ? O4 C6 C1 115.59(18) ? C5 C6 C1 118.7(2) ? O4 C7 H7A 109.5 ? O4 C7 H7B 109.5 ? H7A C7 H7B 109.5 ? O4 C7 H7C 109.5 ? H7A C7 H7C 109.5 ? H7B C7 H7C 109.5 ? N2 C8 C11 122.51(15) ? N2 C8 C9 112.68(16) y C11 C8 C9 124.8(2) y O3 C9 C8 124.6(2) y O3 C9 C10 121.01(16) ? C8 C9 C10 114.38(15) y C9 C10 Cl1 112.93(14) ? C9 C10 H10A 109.0 ? Cl1 C10 H10A 109.0 ? C9 C10 H10B 109.0 ? Cl1 C10 H10B 109.0 ? H10A C10 H10B 107.8 ? O1 C11 O2 123.04(18) y O1 C11 C8 121.8(2) ? O2 C11 C8 115.15(15) y O2 C12 C13 107.74(17) ? O2 C12 H12A 110.2 ? C13 C12 H12A 110.2 ? O2 C12 H12B 110.2 ? C13 C12 H12B 110.2 ? H12A C12 H12B 108.5 ? C12 C13 H13A 109.5 ? C12 C13 H13B 109.5 ? H13A C13 H13B 109.5 ? C12 C13 H13C 109.5 ? H13A C13 H13C 109.5 ? H13B C13 H13C 109.5 ? N2 N1 C1 118.9(2) y N2 N1 H1 121.6(18) ? C1 N1 H1 119.1(18) ? N1 N2 C8 122.97(16) y C11 O2 C12 115.11(15) ? C6 O4 C7 117.03(19) ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag C1 C2 1.370(3) ? C1 C6 1.392(3) ? C1 N1 1.408(2) ? C2 C3 1.382(3) ? C2 H2 0.93 ? C3 C4 1.376(4) ? C3 H3 0.93 ? C4 C5 1.362(4) ? C4 H4 0.93 ? C5 C6 1.389(3) ? C5 H5 0.93 ? C6 O4 1.368(3) y C7 O4 1.419(3) y C7 H7A 0.96 ? C7 H7B 0.96 ? C7 H7C 0.96 ? C8 N2 1.311(2) ? C8 C11 1.473(3) ? C8 C9 1.475(2) ? C9 O3 1.203(2) y C9 C10 1.516(3) ? C10 Cl1 1.766(2) ? C10 H10A 0.97 ? C10 H10B 0.97 ? C11 O1 1.215(2) y C11 O2 1.321(2) y C12 O2 1.451(2) y C12 C13 1.491(3) ? C12 H12A 0.97 ? C12 H12B 0.97 ? C13 H13A 0.96 ? C13 H13B 0.96 ? C13 H13C 0.96 ? N1 N2 1.300(2) ? N1 H1 0.79(2) ? 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 C5 H5 O3 1_454 0.93 2.56 3.413(3) 153 N1 H1 O1 . 0.79(2) 2.02(2) 2.602(2) 131(2) N1 H1 O4 . 0.79(2) 2.31(2) 2.635(2) 106(2) 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 C6 C1 C2 C3 1.4(3) ? N1 C1 C2 C3 -176.44(19) ? C1 C2 C3 C4 -0.8(4) ? C2 C3 C4 C5 -0.5(4) ? C3 C4 C5 C6 1.1(4) ? C4 C5 C6 O4 178.8(2) ? C4 C5 C6 C1 -0.5(3) ? C2 C1 C6 O4 179.86(18) ? N1 C1 C6 O4 -2.2(2) y C2 C1 C6 C5 -0.8(3) ? N1 C1 C6 C5 177.21(18) ? N2 C8 C9 O3 -179.88(17) ? C11 C8 C9 O3 0.6(3) ? N2 C8 C9 C10 2.1(2) ? C11 C8 C9 C10 -177.41(18) ? O3 C9 C10 Cl1 15.7(3) ? C8 C9 C10 Cl1 -166.16(14) ? N2 C8 C11 O1 1.0(3) ? C9 C8 C11 O1 -179.55(18) ? N2 C8 C11 O2 -179.07(16) ? C9 C8 C11 O2 0.4(3) ? C2 C1 N1 N2 -2.2(3) ? C6 C1 N1 N2 179.89(16) ? C1 N1 N2 C8 174.2(2) y C11 C8 N2 N1 -0.8(3) ? C9 C8 N2 N1 179.69(16) ? O1 C11 O2 C12 -0.2(3) ? C8 C11 O2 C12 179.9(2) ? C13 C12 O2 C11 177.42(18) ? C5 C6 O4 C7 -7.0(3) ? C1 C6 O4 C7 172.30(19) ? loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 21180294 2 PubChem 139068410