#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:43:10 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301803 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/37/2203740.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_2203740 loop_ _publ_author_name 'Thamotharan, S.' 'Parthasarathi, V.' 'Kalaivani, P.' 'Mallur, Shanta G.' 'Badami, Bharati' 'Schenk, Kurt J.' _publ_section_title ; 3-(4-Chlorophenyl)-5-methyl-3H-1,3,4-oxadiazol-2-one ; _journal_issue 6 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o964 _journal_page_last o965 _journal_paper_doi 10.1107/S1600536804010967 _journal_volume 60 _journal_year 2004 _chemical_formula_iupac 'C9 H7 Cl N2 O2' _chemical_formula_moiety 'C9 H7 Cl N2 O2' _chemical_formula_sum 'C9 H7 Cl N2 O2' _chemical_formula_weight 210.62 _chemical_melting_point 372 _chemical_name_systematic ; 3-(4-Chlorophenyl)-5-methyl-3H-1,3,4-oxadiazole-2-one ; _space_group_IT_number 56 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall '-P 2ac 2bc' _symmetry_space_group_name_H-M 'P n a a' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 8 _cell_length_a 6.8548(14) _cell_length_b 12.042(2) _cell_length_c 22.762(5) _cell_measurement_reflns_used 6328 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 27.9 _cell_measurement_theta_min 3.45 _cell_volume 1878.9(6) _computing_cell_refinement IPDS _computing_data_collection 'IPDS (Stoe & Cie, 1997)' _computing_data_reduction IPDS _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_publication_material 'SHELXL97 and PLATON (Spek, 2003)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 0.943 _diffrn_measured_fraction_theta_max 0.943 _diffrn_measurement_device_type 'Stoe IPDS-I' _diffrn_measurement_method '\w rotation method' _diffrn_radiation_monochromator 'plane graphite' _diffrn_radiation_source 'sealed LFF X-ray tube, 12x0.4 mm' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0433 _diffrn_reflns_av_sigmaI/netI 0.0179 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_number 15537 _diffrn_reflns_theta_full 28.01 _diffrn_reflns_theta_max 28.01 _diffrn_reflns_theta_min 3.54 _diffrn_standards_decay_% 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.379 _exptl_absorpt_correction_T_max 0.9137 _exptl_absorpt_correction_T_min 0.8498 _exptl_absorpt_correction_type integration _exptl_absorpt_process_details '(X-RED1.22 in IPDS; Stoe & Cie, 1997)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.489 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 864 _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.12 _refine_diff_density_max 0.287 _refine_diff_density_min -0.192 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.076 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 128 _refine_ls_number_reflns 2140 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.076 _refine_ls_R_factor_all 0.0639 _refine_ls_R_factor_gt 0.0583 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0844P)^2^+0.5325P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1638 _refine_ls_wR_factor_ref 0.1676 _reflns_number_gt 1841 _reflns_number_total 2140 _reflns_threshold_expression I>2\s(I) _cod_data_source_file cv6311.cif _cod_data_source_block I _cod_original_cell_volume 1878.9(7) _cod_database_code 2203740 _cod_database_fobs_code 2203740 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x, -y+1/2, -z+1/2' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x, y-1/2, z-1/2' 'x-1/2, -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_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_type_symbol Cl1 0.14863(14) 0.64195(5) 0.19705(3) 0.0935(3) Uani d . 1 Cl O1 0.1821(2) 0.04206(12) 0.03948(6) 0.0683(4) Uani d . 1 O O2 0.2014(3) 0.20942(14) -0.00749(7) 0.0892(6) Uani d . 1 O N3 0.1607(2) 0.18975(13) 0.09417(7) 0.0532(4) Uani d . 1 N N4 0.1486(3) 0.09866(13) 0.13173(7) 0.0578(4) Uani d . 1 N C2 0.1833(3) 0.15714(18) 0.03729(8) 0.0627(5) Uani d . 1 C C5 0.1596(3) 0.01473(17) 0.09759(9) 0.0599(5) Uani d . 1 C C51 0.1552(4) -0.10445(19) 0.11336(12) 0.0774(7) Uani d . 1 C H511 0.1454 -0.1119 0.1552 0.116 Uiso calc R 1 H H512 0.2728 -0.1396 0.0999 0.116 Uiso calc R 1 H H513 0.0446 -0.1391 0.0951 0.116 Uiso calc R 1 H C6 0.1569(3) 0.29986(14) 0.11714(7) 0.0496(4) Uani d . 1 C C7 0.1624(3) 0.39223(16) 0.08088(8) 0.0566(5) Uani d . 1 C H7 0.1676 0.3838 0.0403 0.068 Uiso calc R 1 H C8 0.1599(3) 0.49763(17) 0.10573(9) 0.0613(5) Uani d . 1 C H8 0.1648 0.5602 0.0818 0.074 Uiso calc R 1 H C9 0.1502(3) 0.50931(16) 0.16603(10) 0.0616(5) Uani d . 1 C C10 0.1442(4) 0.41825(19) 0.20248(9) 0.0707(7) Uani d . 1 C H10 0.1394 0.4271 0.2430 0.085 Uiso calc R 1 H C11 0.1455(4) 0.31275(16) 0.17766(8) 0.0657(6) Uani d . 1 C H11 0.1388 0.2505 0.2017 0.079 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 Cl1 0.1578(8) 0.0448(3) 0.0778(4) -0.0017(3) 0.0057(4) -0.0104(2) O1 0.0989(11) 0.0554(8) 0.0506(8) -0.0014(7) -0.0002(7) -0.0130(6) O2 0.1531(18) 0.0716(10) 0.0430(7) -0.0030(10) 0.0101(9) -0.0032(7) N3 0.0751(10) 0.0444(8) 0.0400(7) -0.0021(6) 0.0013(6) -0.0037(5) N4 0.0803(11) 0.0454(8) 0.0476(8) -0.0025(7) 0.0004(7) -0.0010(6) C2 0.0865(14) 0.0575(11) 0.0440(9) -0.0025(9) 0.0009(8) -0.0086(7) C5 0.0762(13) 0.0503(10) 0.0532(10) -0.0024(8) -0.0028(8) -0.0079(8) C51 0.1085(19) 0.0472(11) 0.0766(15) -0.0037(10) -0.0032(12) -0.0062(10) C6 0.0627(10) 0.0437(9) 0.0425(8) -0.0024(7) 0.0012(7) -0.0032(6) C7 0.0742(12) 0.0549(10) 0.0406(8) -0.0041(8) 0.0028(7) 0.0025(7) C8 0.0830(14) 0.0476(10) 0.0535(10) -0.0015(8) 0.0038(9) 0.0080(8) C9 0.0872(14) 0.0424(9) 0.0552(10) 0.0005(8) 0.0024(9) -0.0029(7) C10 0.121(2) 0.0494(11) 0.0417(9) -0.0013(10) 0.0045(10) -0.0036(7) C11 0.1121(17) 0.0444(9) 0.0406(9) 0.0001(9) 0.0020(9) 0.0011(7) 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' Cl Cl 0.1484 0.1585 '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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C5 O1 C2 105.96(15) C2 N3 N4 111.30(15) C2 N3 C6 128.24(16) N4 N3 C6 120.41(14) C5 N4 N3 104.25(16) O2 C2 N3 131.7(2) O2 C2 O1 123.59(18) N3 C2 O1 104.68(17) N4 C5 O1 113.81(18) N4 C5 C51 128.2(2) O1 C5 C51 117.96(19) C5 C51 H511 109.5 C5 C51 H512 109.5 H511 C51 H512 109.5 C5 C51 H513 109.5 H511 C51 H513 109.5 H512 C51 H513 109.5 C7 C6 C11 120.18(17) C7 C6 N3 121.86(16) C11 C6 N3 117.96(16) C6 C7 C8 119.37(17) C6 C7 H7 120.3 C8 C7 H7 120.3 C9 C8 C7 119.87(18) C9 C8 H8 120.1 C7 C8 H8 120.1 C10 C9 C8 121.30(18) C10 C9 Cl1 119.01(16) C8 C9 Cl1 119.68(16) C9 C10 C11 118.88(18) C9 C10 H10 120.6 C11 C10 H10 120.6 C6 C11 C10 120.38(18) C6 C11 H11 119.8 C10 C11 H11 119.8 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance Cl1 C9 1.746(2) O1 C5 1.372(3) O1 C2 1.387(3) O2 C2 1.205(3) N3 C2 1.362(2) N3 N4 1.393(2) N3 C6 1.425(2) N4 C5 1.277(2) C5 C51 1.480(3) C51 H511 0.9600 C51 H512 0.9600 C51 H513 0.9600 C6 C7 1.386(3) C6 C11 1.388(2) C7 C8 1.390(3) C7 H7 0.9300 C8 C9 1.381(3) C8 H8 0.9300 C9 C10 1.376(3) C10 C11 1.390(3) C10 H10 0.9300 C11 H11 0.9300 loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag C7 H7 O2 0.93 2.38 2.994(3) 124 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 C2 N3 N4 C5 -1.3(2) C6 N3 N4 C5 -178.86(17) N4 N3 C2 O2 -179.0(3) C6 N3 C2 O2 -1.7(4) N4 N3 C2 O1 0.9(2) C6 N3 C2 O1 178.27(17) C5 O1 C2 O2 179.7(2) C5 O1 C2 N3 -0.2(2) N3 N4 C5 O1 1.1(2) N3 N4 C5 C51 179.8(2) C2 O1 C5 N4 -0.6(3) C2 O1 C5 C51 -179.4(2) C2 N3 C6 C7 5.0(3) N4 N3 C6 C7 -177.89(17) C2 N3 C6 C11 -175.6(2) N4 N3 C6 C11 1.5(3) C11 C6 C7 C8 1.1(3) N3 C6 C7 C8 -179.45(17) C6 C7 C8 C9 -0.6(3) C7 C8 C9 C10 0.5(4) C7 C8 C9 Cl1 179.62(16) C8 C9 C10 C11 -0.9(4) Cl1 C9 C10 C11 -179.99(18) C7 C6 C11 C10 -1.5(3) N3 C6 C11 C10 179.0(2) C9 C10 C11 C6 1.4(4) loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 8211608 2 PubChem 10036043