#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:43:10 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301803 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/45/2204500.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_2204500 loop_ _publ_author_name 'Wang, Hai-Bo' 'Chen, Jia-Hui' 'Pu, Yue-Qing' 'Wang, Jin-Tang' _publ_section_title ; Methyl 2-{[3-(4-methylsulfanyl)phenyl-1,2,4-oxadiazol-5-yl]methoxy}phenylacetate ; _journal_issue 11 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o2122 _journal_page_last o2124 _journal_paper_doi 10.1107/S1600536804026649 _journal_volume 60 _journal_year 2004 _chemical_formula_iupac 'C19 H18 N2 O4 S' _chemical_formula_moiety 'C19 H18 N2 O4 S' _chemical_formula_sum 'C19 H18 N2 O4 S' _chemical_formula_weight 370.41 _chemical_name_systematic ; Methyl 2-{[3-(4-methylsulfanyl)phenyl-1,2,4-oxadiazol- 5-yl]methoxy}phenylacetate ; _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 _cell_angle_alpha 90.13(3) _cell_angle_beta 102.08(3) _cell_angle_gamma 99.73(3) _cell_formula_units_Z 2 _cell_length_a 8.3580(17) _cell_length_b 10.522(2) _cell_length_c 10.581(2) _cell_measurement_reflns_used 25 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 13 _cell_measurement_theta_min 10 _cell_volume 896.1(3) _computing_cell_refinement 'CAD-4 Software' _computing_data_collection 'CAD-4 Software (Enraf-Nonius, 1989)' _computing_data_reduction 'XCAD4 (Harms & Wocadlo, 1995)' _computing_molecular_graphics 'SHELXTL (Siemens, 1996)' _computing_publication_material SHELXTL _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type '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 0.71073 _diffrn_reflns_av_R_equivalents 0.0205 _diffrn_reflns_av_sigmaI/netI 0.0242 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 3752 _diffrn_reflns_theta_full 25.97 _diffrn_reflns_theta_max 25.97 _diffrn_reflns_theta_min 1.97 _diffrn_standards_decay_% 0 _diffrn_standards_interval_count 200 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.208 _exptl_absorpt_correction_type none _exptl_crystal_colour Colourless _exptl_crystal_density_diffrn 1.373 _exptl_crystal_density_method 'not measured' _exptl_crystal_description Block _exptl_crystal_F_000 388 _exptl_crystal_size_max .4 _exptl_crystal_size_mid .3 _exptl_crystal_size_min .3 _refine_diff_density_max 0.324 _refine_diff_density_min -0.205 _refine_ls_extinction_coef 0.036(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL97 _refine_ls_goodness_of_fit_ref 0.906 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 236 _refine_ls_number_reflns 3499 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.906 _refine_ls_R_factor_all 0.0554 _refine_ls_R_factor_gt 0.0406 _refine_ls_shift/su_max 0.014 _refine_ls_shift/su_mean 0.003 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.1P)^2^+0.35P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1276 _refine_ls_wR_factor_ref 0.1419 _reflns_number_gt 2763 _reflns_number_total 3499 _reflns_threshold_expression I>2\s(I) _cod_data_source_file fl6129.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 2204500 _cod_database_fobs_code 2204500 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 S 0.10592(7) -0.01231(6) 0.85337(7) 0.0594(2) Uani d . 1 S O1 0.84214(18) -0.42310(16) 1.09084(14) 0.0513(4) Uani d . 1 O N2 0.6154(2) -0.41523(16) 1.16328(15) 0.0406(4) Uani d . 1 N O4 0.60500(19) -0.87935(14) 1.60436(19) 0.0610(5) Uani d . 1 O O3 0.84235(17) -0.74158(15) 1.66992(18) 0.0590(5) Uani d . 1 O O2 0.73315(17) -0.57758(13) 1.37455(13) 0.0406(3) Uani d . 1 O N1 0.7524(2) -0.3417(2) 1.00828(18) 0.0538(5) Uani d . 1 N C1 0.1752(3) 0.0760(3) 0.7257(3) 0.0715(8) Uani d . 1 C H1B 0.0988 0.1325 0.6921 0.107 Uiso calc R 1 H H1C 0.1807 0.0171 0.6580 0.107 Uiso calc R 1 H H1D 0.2834 0.1261 0.7582 0.107 Uiso calc R 1 H C2 0.2567(3) -0.1099(2) 0.9043(2) 0.0444(5) Uani d . 1 C C3 0.4027(3) -0.1014(2) 0.8583(2) 0.0559(6) Uani d . 1 C H3A 0.4219 -0.0440 0.7942 0.067 Uiso calc R 1 H C4 0.5187(3) -0.1773(2) 0.9070(2) 0.0537(6) Uani d . 1 C H4A 0.6153 -0.1704 0.8752 0.064 Uiso calc R 1 H C5 0.4938(2) -0.26386(19) 1.00257(18) 0.0402(4) Uani d . 1 C C6 0.3469(3) -0.2735(2) 1.04728(19) 0.0448(5) Uani d . 1 C H6A 0.3274 -0.3316 1.1106 0.054 Uiso calc R 1 H C7 0.2297(3) -0.1976(2) 0.9987(2) 0.0476(5) Uani d . 1 C H7A 0.1322 -0.2055 1.0295 0.057 Uiso calc R 1 H C8 0.6211(2) -0.34094(18) 1.05643(18) 0.0381(4) Uani d . 1 C C9 0.7519(2) -0.46117(19) 1.17841(18) 0.0377(4) Uani d . 1 C C10 0.8221(3) -0.5517(2) 1.27483(19) 0.0428(5) Uani d . 1 C H10A 0.8220 -0.6324 1.2302 0.051 Uiso calc R 1 H H10B 0.9366 -0.5151 1.3132 0.051 Uiso calc R 1 H C11 0.7634(2) -0.48744(17) 1.47516(17) 0.0331(4) Uani d . 1 C C12 0.8581(2) -0.36543(18) 1.47633(19) 0.0379(4) Uani d . 1 C H12A 0.9068 -0.3402 1.4069 0.045 Uiso calc R 1 H C13 0.8792(2) -0.28157(18) 1.5822(2) 0.0427(5) Uani d . 1 C H13A 0.9427 -0.1998 1.5834 0.051 Uiso calc R 1 H C14 0.8075(3) -0.3176(2) 1.6855(2) 0.0451(5) Uani d . 1 C H14A 0.8222 -0.2607 1.7560 0.054 Uiso calc R 1 H C15 0.7130(2) -0.4400(2) 1.68307(19) 0.0417(4) Uani d . 1 C H15A 0.6640 -0.4643 1.7526 0.050 Uiso calc R 1 H C16 0.6901(2) -0.52673(17) 1.57939(18) 0.0347(4) Uani d . 1 C C17 0.5908(2) -0.66007(18) 1.5795(2) 0.0399(4) Uani d . 1 C H17A 0.5144 -0.6591 1.6369 0.048 Uiso calc R 1 H H17B 0.5253 -0.6835 1.4930 0.048 Uiso calc R 1 H C18 0.6967(2) -0.76086(18) 1.62162(19) 0.0387(4) Uani d . 1 C C19 0.6930(3) -0.9844(2) 1.6429(3) 0.0695(8) Uani d . 1 C H19A 0.6168 -1.0647 1.6265 0.104 Uiso calc R 1 H H19B 0.7428 -0.9741 1.7336 0.104 Uiso calc R 1 H H19C 0.7781 -0.9842 1.5944 0.104 Uiso calc R 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 S 0.0496(4) 0.0545(4) 0.0744(4) 0.0224(3) 0.0032(3) 0.0129(3) O1 0.0459(8) 0.0694(10) 0.0489(8) 0.0278(7) 0.0186(7) 0.0195(7) N2 0.0390(9) 0.0491(9) 0.0377(8) 0.0168(7) 0.0095(7) 0.0106(7) O4 0.0432(8) 0.0390(8) 0.0927(12) 0.0088(7) -0.0053(8) 0.0097(8) O3 0.0306(8) 0.0540(9) 0.0915(12) 0.0107(6) 0.0077(7) 0.0242(8) O2 0.0427(7) 0.0415(7) 0.0384(7) 0.0097(6) 0.0086(6) 0.0044(6) N1 0.0543(11) 0.0688(12) 0.0483(10) 0.0280(9) 0.0193(8) 0.0221(9) C1 0.0643(16) 0.0594(15) 0.0851(19) 0.0155(12) -0.0007(14) 0.0268(13) C2 0.0419(11) 0.0424(11) 0.0467(11) 0.0120(8) 0.0009(8) 0.0028(8) C3 0.0573(13) 0.0583(13) 0.0584(13) 0.0215(11) 0.0173(11) 0.0256(11) C4 0.0501(12) 0.0630(14) 0.0559(13) 0.0226(11) 0.0190(10) 0.0223(11) C5 0.0411(10) 0.0437(10) 0.0366(9) 0.0131(8) 0.0055(8) 0.0052(8) C6 0.0472(11) 0.0507(11) 0.0389(10) 0.0144(9) 0.0091(9) 0.0114(8) C7 0.0408(11) 0.0553(12) 0.0491(12) 0.0152(9) 0.0097(9) 0.0065(9) C8 0.0397(10) 0.0420(10) 0.0335(9) 0.0113(8) 0.0064(8) 0.0032(7) C9 0.0369(10) 0.0445(10) 0.0339(9) 0.0131(8) 0.0079(7) 0.0018(8) C10 0.0445(11) 0.0519(11) 0.0378(10) 0.0227(9) 0.0104(8) 0.0070(8) C11 0.0275(8) 0.0365(9) 0.0364(9) 0.0122(7) 0.0037(7) 0.0071(7) C12 0.0315(9) 0.0407(10) 0.0425(10) 0.0091(7) 0.0077(7) 0.0121(8) C13 0.0360(10) 0.0351(10) 0.0557(12) 0.0079(8) 0.0055(9) 0.0063(8) C14 0.0442(11) 0.0450(11) 0.0484(11) 0.0158(9) 0.0085(9) -0.0017(9) C15 0.0368(10) 0.0517(11) 0.0418(10) 0.0156(8) 0.0133(8) 0.0093(8) C16 0.0261(8) 0.0390(10) 0.0408(10) 0.0116(7) 0.0064(7) 0.0113(8) C17 0.0290(9) 0.0422(10) 0.0491(11) 0.0088(8) 0.0077(8) 0.0132(8) C18 0.0317(10) 0.0417(10) 0.0447(10) 0.0085(8) 0.0112(8) 0.0127(8) C19 0.0626(15) 0.0425(12) 0.101(2) 0.0193(11) 0.0048(14) 0.0129(13) 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' S S 0.1246 0.1234 '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 S C1 104.11(12) yes C9 O1 N1 106.07(14) yes C11 O2 C10 118.04(15) yes C18 O4 C19 115.95(17) yes C8 N1 O1 103.23(16) yes C9 N2 C8 102.45(16) yes S C1 H1B 109.5 ? S C1 H1C 109.5 ? H1B C1 H1C 109.5 ? S C1 H1D 109.5 ? H1B C1 H1D 109.5 ? H1C C1 H1D 109.5 ? C7 C2 C3 118.65(19) ? C7 C2 S 117.43(17) yes C3 C2 S 123.89(17) ? C4 C3 C2 120.6(2) ? C4 C3 H3A 119.7 ? C2 C3 H3A 119.7 ? C3 C4 C5 121.1(2) ? C3 C4 H4A 119.4 ? C5 C4 H4A 119.4 ? C4 C5 C6 118.25(19) ? C4 C5 C8 120.43(18) yes C6 C5 C8 121.30(18) ? C7 C6 C5 120.94(19) ? C7 C6 H6A 119.5 ? C5 C6 H6A 119.5 ? C6 C7 C2 120.4(2) ? C6 C7 H7A 119.8 ? C2 C7 H7A 119.8 ? N1 C8 N2 114.38(17) yes N1 C8 C5 122.09(18) yes N2 C8 C5 123.50(17) yes N2 C9 O1 113.87(17) yes N2 C9 C10 130.83(18) yes O1 C9 C10 115.29(16) yes O2 C10 C9 113.34(15) yes O2 C10 H10A 108.9 ? C9 C10 H10A 108.9 ? O2 C10 H10B 108.9 ? C9 C10 H10B 108.9 ? H10A C10 H10B 107.7 ? O2 C11 C12 123.99(17) yes O2 C11 C16 115.13(16) yes C12 C11 C16 120.88(17) ? C13 C12 C11 119.26(18) ? C13 C12 H12A 120.4 ? C11 C12 H12A 120.4 ? C14 C13 C12 120.98(18) ? C14 C13 H13A 119.5 ? C12 C13 H13A 119.5 ? C13 C14 C15 119.16(19) ? C13 C14 H14A 120.4 ? C15 C14 H14A 120.4 ? C16 C15 C14 121.49(18) ? C16 C15 H15A 119.3 ? C14 C15 H15A 119.3 ? C15 C16 C11 118.23(17) ? C15 C16 C17 120.89(17) yes C11 C16 C17 120.87(17) yes C18 C17 C16 113.25(15) yes C18 C17 H17A 108.9 ? C16 C17 H17A 108.9 ? C18 C17 H17B 108.9 ? C16 C17 H17B 108.9 ? H17A C17 H17B 107.7 ? O3 C18 O4 122.65(18) yes O3 C18 C17 126.41(18) yes O4 C18 C17 110.87(16) yes O4 C19 H19A 109.5 ? O4 C19 H19B 109.5 ? H19A C19 H19B 109.5 ? O4 C19 H19C 109.5 ? H19A C19 H19C 109.5 ? H19B C19 H19C 109.5 ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag S C2 1.757(2) yes S C1 1.782(3) yes O1 C9 1.334(2) yes O1 N1 1.416(2) yes O2 C10 1.415(2) yes O2 C11 1.378(2) yes O3 C18 1.200(2) yes O4 C18 1.339(2) yes O4 C19 1.442(3) yes N1 C8 1.304(3) yes N2 C8 1.380(2) yes N2 C9 1.292(2) yes C1 H1B 0.9600 ? C1 H1C 0.9600 ? C1 H1D 0.9600 ? C2 C7 1.389(3) ? C2 C3 1.395(3) ? C3 C4 1.377(3) ? C3 H3A 0.9300 ? C4 C5 1.387(3) ? C4 H4A 0.9300 ? C5 C6 1.393(3) ? C5 C8 1.468(3) yes C6 C7 1.384(3) ? C6 H6A 0.9300 ? C7 H7A 0.9300 ? C9 C10 1.496(3) yes C10 H10A 0.9700 ? C10 H10B 0.9700 ? C11 C12 1.388(3) ? C11 C16 1.401(3) ? C12 C13 1.387(3) ? C12 H12A 0.9300 ? C13 C14 1.378(3) ? C13 H13A 0.9300 ? C14 C15 1.390(3) ? C14 H14A 0.9300 ? C15 C16 1.386(3) ? C15 H15A 0.9300 ? C16 C17 1.505(3) yes C17 C18 1.504(2) yes C17 H17A 0.9700 ? C17 H17B 0.9700 ? C19 H19A 0.9600 ? C19 H19B 0.9600 ? C19 H19C 0.9600 ? 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 C12 H12A O3 2_748 0.93 2.43 3.257(3) 148.00 yes C10 H10A Cg2 2_647 0.97 2.77 3.58 142 yes C10 H10B Cg3 2_748 0.97 2.65 3.43 138 yes C17 H17B Cg3 2_648 0.97 2.85 3.42 118 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 C1 S C2 C3 6.3(2) ? C1 S C2 C7 -175.64(19) ? C2 S C1 H1D -59.91 ? C2 S C1 H1B -179.91 ? C2 S C1 H1C 60.09 ? C9 O1 N1 C8 0.2(2) yes N1 O1 C9 C10 178.57(17) yes N1 O1 C9 N2 0.1(2) yes C11 O2 C10 C9 -80.0(2) yes C10 O2 C11 C16 -171.15(17) yes C10 O2 C11 C12 9.2(3) yes C19 O4 C18 C17 -179.3(2) yes C19 O4 C18 O3 -2.3(3) yes O1 N1 C8 C5 177.94(17) yes O1 N1 C8 N2 -0.3(2) yes C9 N2 C8 N1 0.4(2) yes C9 N2 C8 C5 -177.86(18) yes C8 N2 C9 O1 -0.3(2) yes C8 N2 C9 C10 -178.5(2) yes C7 C2 C3 C4 -0.9(3) ? S C2 C3 C4 177.11(17) ? S C2 C7 C6 -177.18(17) ? C3 C2 C7 C6 1.0(3) ? C2 C3 C4 C5 0.00 ? C3 C4 C5 C8 -177.98(19) ? C3 C4 C5 C6 0.8(3) ? C8 C5 C6 C7 178.03(19) ? C6 C5 C8 N2 -8.0(3) yes C4 C5 C6 C7 -0.8(3) ? C4 C5 C8 N2 170.72(19) yes C6 C5 C8 N1 173.9(2) yes C4 C5 C8 N1 -7.4(3) yes C5 C6 C7 C2 -0.1(3) ? N2 C9 C10 O2 -8.8(3) yes O1 C9 C10 O2 173.01(17) yes C12 C11 C16 C17 -178.55(17) ? O2 C11 C16 C17 1.8(2) ? C12 C11 C16 C15 0.8(3) ? O2 C11 C16 C15 -179.(3) ? C16 C11 C12 C13 -0.3(3) ? O2 C11 C12 C13 179.30(17) ? C11 C12 C13 C14 -0.1(3) ? C12 C13 C14 C15 0.1(3) ? C13 C14 C15 C16 0.4(3) ? C14 C15 C16 C11 -0.8(3) ? C14 C15 C16 C17 178.54(19) ? C15 C16 C17 C18 -97.3(2) ? C11 C16 C17 C18 82.0(2) ? C16 C17 C18 O4 -172.09(17) ? C16 C17 C18 O3 11.1(3) ? loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 21130322 2 PubChem 139067119