#------------------------------------------------------------------------------ #$Date: 2025-08-18 23:52:38 +0100 (Mon, 18 Aug 2025) $ #$Revision: 301791 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/52/2005208.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_2005208 loop_ _publ_author_name 'Frydenvang, K.' 'Brehm, L.' 'di Biase, R.' 'Falch, E.' _publ_section_title ; 2-Ethyl-3-(3-pyridyl)-5(2H)-isoxazolone ; _journal_issue 8 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 2102 _journal_page_last 2105 _journal_paper_doi 10.1107/S0108270196006142 _journal_volume 52 _journal_year 1996 _chemical_formula_sum 'C10 H10 N2 O2' _chemical_formula_weight 190.2 _chemical_melting_point .366E-305 _chemical_name_systematic ; 2-Ethyl-3-(3-pyridyl)isoxazolin-5-one ; _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 _cell_angle_beta 91.81(1) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 7.571(1) _cell_length_b 7.1610(7) _cell_length_c 16.535(2) _cell_measurement_reflns_used 18 _cell_measurement_temperature 111(2) _cell_measurement_theta_max 42.94 _cell_measurement_theta_min 33.99 _cell_volume 896.01(18) _computing_cell_refinement 'CAD-4 Software' _computing_data_collection 'CAD-4 Software (Enraf-Nonius, 1989)' _computing_data_reduction 'DREADD (Blessing, 1987, 1989)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_structure_refinement 'SHELXL93 (Sheldrick, 1993)' _computing_structure_solution 'SHELXS86 (Sheldrick, 1990)' _diffrn_ambient_temperature 111(2) _diffrn_measurement_device 'Enraf Nonius CAD-4 diffractometer' _diffrn_measurement_method '\w/2\q scan' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0118 _diffrn_reflns_av_sigmaI/netI 0.0171 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 4033 _diffrn_reflns_theta_max 74.61 _diffrn_reflns_theta_min 5.35 _diffrn_standards_decay_% '-3.8, corrected' _diffrn_standards_interval_count 300 _diffrn_standards_interval_time 166 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.830 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.41 _exptl_crystal_density_method none _exptl_crystal_description prism _exptl_crystal_F_000 400 _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.10 _refine_diff_density_max 0.299 _refine_diff_density_min -0.300 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_all 1.071 _refine_ls_goodness_of_fit_obs 1.101 _refine_ls_hydrogen_treatment refxyz _refine_ls_matrix_type full _refine_ls_number_parameters 157 _refine_ls_number_reflns 1834 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.141 _refine_ls_restrained_S_obs 1.101 _refine_ls_R_factor_all 0.0454 _refine_ls_R_factor_obs 0.0371 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/esd_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0557P)^2^+0.3763P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all 0.1065 _refine_ls_wR_factor_obs 0.0971 _reflns_number_observed 1658 _reflns_number_total 1838 _reflns_observed_criterion >2sigma(I) _cod_data_source_file ab1380.cif _cod_data_source_block ef726 _cod_depositor_comments ; The following automatic conversions were performed: '_refine_ls_weighting_scheme' value 'calc w = 1/[\s^2^(Fo^2^)+(0.0557P)^2^+0.3763P] 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^)+(0.0557P)^2^+0.3763P] 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 896.0(2) _cod_original_sg_symbol_H-M P21/n _cod_database_code 2005208 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 0.0119(4) 0.0253(5) 0.0172(4) -0.0001(3) -0.0049(3) 0.0002(3) N2 0.0102(5) 0.0231(5) 0.0147(5) -0.0008(4) -0.0035(4) -0.0004(4) C3 0.0154(6) 0.0120(5) 0.0159(6) 0.0005(4) -0.0002(4) 0.0008(4) C4 0.0152(6) 0.0200(6) 0.0198(6) 0.0020(4) 0.0017(4) 0.0024(5) C5 0.0142(6) 0.0178(6) 0.0235(6) 0.0005(4) 0.0000(5) 0.0042(5) O2 0.0135(4) 0.0341(5) 0.0319(5) -0.0001(4) -0.0053(4) 0.0057(4) C6 0.0149(5) 0.0152(5) 0.0136(5) -0.0016(4) -0.0002(4) 0.0019(4) C7 0.0163(6) 0.0203(6) 0.0149(5) 0.0001(5) -0.0006(4) 0.0004(4) N8 0.0176(5) 0.0250(6) 0.0177(5) -0.0010(4) -0.0033(4) 0.0033(4) C9 0.0242(6) 0.0231(6) 0.0156(6) -0.0069(5) -0.0051(5) 0.0044(5) C10 0.0314(7) 0.0198(6) 0.0141(6) -0.0052(5) -0.0001(5) -0.0008(5) C11 0.0229(6) 0.0176(6) 0.0161(6) -0.0005(5) 0.0025(5) 0.0006(5) C12 0.0138(5) 0.0205(6) 0.0144(5) -0.0011(4) 0.0006(4) 0.0004(4) C13 0.0208(6) 0.0279(7) 0.0179(6) 0.0007(5) 0.0031(5) -0.0045(5) loop_ _atom_site_label _atom_site_occupancy _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_type_symbol O1 1 .2471(1) .0826(1) .18706(5) .0183(2) Uani d O N2 1 .4084(1) .0772(2) .23301(6) .0161(2) Uani d N C3 1 .3691(2) .1160(2) .31162(7) .0145(3) Uani d C C4 1 .1910(2) .1278(2) .31949(8) .0183(3) Uani d C C5 1 .1102(2) .1083(2) .24081(8) .0185(3) Uani d C O2 1 -.0409(1) .1056(1) .21404(6) .0266(2) Uani d O C6 1 .5094(2) .1285(2) .37490(7) .0146(3) Uani d C C7 1 .6657(2) .0264(2) .37072(7) .0172(3) Uani d C N8 1 .7956(1) .0314(2) .42752(6) .0202(2) Uani d N C9 1 .7699(2) .1394(2) .49220(7) .0211(3) Uani d C C10 1 .6173(2) .2430(2) .50325(7) .0218(3) Uani d C C11 1 .4850(2) .2384(2) .44335(7) .0188(3) Uani d C C12 1 .5497(2) .1639(2) .18728(7) .0162(3) Uani d C C13 1 .6002(2) .0407(2) .11723(8) .0221(3) Uani d C H4 1 .127(3) .142(3) .368(1) .05 Uiso d H H7 1 .682(3) -.056(3) .325(1) .05 Uiso d H H9 1 .867(3) .140(3) .533(1) .05 Uiso d H H10 1 .603(3) .312(3) .553(1) .05 Uiso d H H11 1 .376(3) .316(3) .448(1) .05 Uiso d H H121 1 .508(3) .290(3) .168(1) .05 Uiso d H H122 1 .648(3) .181(3) .226(1) .05 Uiso d H H131 1 .646(3) -.082(3) .138(1) .05 Uiso d H H132 1 .497(3) .019(3) .081(1) .05 Uiso d H H133 1 .694(3) .104(3) .087(1) .05 Uiso d H loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 '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 C5 O1 N2 107.82(8) yes O1 N2 C3 107.05(9) yes N2 C3 C4 110.40(10) yes C3 C4 C5 107.70(10) yes C4 C5 O1 106.70(10) yes O2 C5 O1 118.40(10) yes O2 C5 C4 134.90(10) yes N2 C3 C6 120.90(10) yes C4 C3 C6 128.60(10) yes C3 C6 C7 121.90(10) yes C3 C6 C11 120.00(10) yes C7 C6 C11 118.00(10) yes C6 C7 N8 123.80(10) yes C7 N8 C9 117.00(10) yes N8 C9 C10 123.80(10) yes C9 C10 C11 118.60(10) yes C10 C11 C6 118.80(10) yes O1 N2 C12 109.97(9) yes C3 N2 C12 125.90(10) yes N2 C12 C13 110.70(10) yes C3 C4 H4 128.0(10) ? C5 C4 H4 124.0(10) ? C6 C7 H7 119.0(10) ? N8 C7 H7 117.0(10) ? N8 C9 H9 115.0(10) ? C10 C9 H9 121.0(10) ? C9 C10 H10 120.0(10) ? C11 C10 H10 121.0(10) ? C6 C11 H11 120.0(10) ? C10 C11 H11 121.0(10) ? N2 C12 H121 108.0(10) ? C13 C12 H121 111.0(10) ? N2 C12 H122 105.0(10) ? C13 C12 H122 112.0(10) ? H121 C12 H122 109(2) ? C12 C13 H131 110.0(10) ? C12 C13 H132 110.0(10) ? C12 C13 H133 109.0(10) ? H131 C13 H132 109(2) ? H131 C13 H133 109(2) ? H132 C13 H133 109(2) ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag O1 N2 1.4180(10) yes N2 C3 1.371(2) yes C3 C4 1.362(2) yes C4 C5 1.427(2) yes O1 C5 1.399(2) yes O2 C5 1.214(2) yes C3 C6 1.470(2) yes C6 C7 1.395(2) yes C7 N8 1.339(2) yes N8 C9 1.339(2) yes C9 C10 1.390(2) yes C10 C11 1.386(2) yes C11 C6 1.395(2) yes N2 C12 1.467(2) yes C12 C13 1.514(2) yes C4 H4 0.95(2) ? C7 H7 0.98(2) ? C9 H9 0.98(2) ? C10 H10 0.96(2) ? C11 H11 1.00(2) ? C12 H121 1.00(2) ? C12 H122 0.98(2) ? C13 H131 1.00(2) ? C13 H132 0.99(2) ? C13 H133 0.99(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 O1 N2 C3 C4 5.90(10) yes N2 C3 C4 C5 -4.10(10) yes C3 C4 C5 O1 0.70(10) yes C4 C5 O1 N2 2.90(10) yes C5 O1 N2 C3 -5.30(10) yes O1 N2 C12 C13 -71.40(10) yes C4 C3 C6 C11 -30.8(2) yes N2 C3 C6 C7 -29.5(2) yes loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 21138227 2 PubChem 139055067