#------------------------------------------------------------------------------ #$Date: 2008-03-30 11:21:05 +0100 (Sun, 30 Mar 2008) $ #$Revision: 321 $ #$URL: svn://www.crystallography.net/cod/cif/2/2203359.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_2203359 loop_ _publ_author_name 'Sema \"Ozt\"urk' 'Mehmet Akkurt' 'Ahmet Cans\?iz' 'Ahmet \,Cetin' 'Mehmet \,Sekerci' 'Frank W. Heinemann' _publ_section_title ; 5-(Furan-2-yl)-1,3,4-oxadiazole-2(3H)-thione ; _journal_issue 3 _journal_name_full 'Acta Crystallographica, Section E' _journal_page_first o322 _journal_page_last o323 _journal_volume 60 _journal_year 2004 _chemical_formula_iupac 'C6 H4 N2 O2 S' _chemical_formula_moiety 'C6 H4 N2 O2 S' _chemical_formula_sum 'C6 H4 N2 O2 S' _chemical_formula_weight 168.18 _chemical_name_systematic ; 5-Furan-2-yl-1,3,4-oxadiazole-2(3H)-thione ; _symmetry_cell_setting Monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 21/c' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 90 _cell_angle_beta 102.573(5) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 5.194(5) _cell_length_b 20.102(5) _cell_length_c 6.914(5) _cell_measurement_reflns_used 145 _cell_measurement_temperature 100 _cell_measurement_theta_max 20. _cell_measurement_theta_min 6. _cell_volume 704.6(9) _computing_cell_refinement 'EVALCCD (Duisenberg, 1998)' _computing_data_collection 'COLLECT (Nonius, 1999)' _computing_data_reduction EVALCCD _computing_molecular_graphics 'ORTEP-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 100 _diffrn_detector_area_resol_mean 9 _diffrn_measured_fraction_theta_full 0.992 _diffrn_measured_fraction_theta_max 0.992 _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method '\f and \w-scans (per frame) with 1.6\% and 32 sec per frame' _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 0.0248 _diffrn_reflns_av_sigmaI/netI 0.0178 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_number 15534 _diffrn_reflns_reduction_process ' ?' _diffrn_reflns_theta_full 28.99 _diffrn_reflns_theta_max 28.99 _diffrn_reflns_theta_min 3.64 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.402 _exptl_absorpt_correction_T_max 0.928 _exptl_absorpt_correction_T_min 0.879 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details '(SADABS, Sheldrick, 1996)' _exptl_crystal_colour 'pale yellow' _exptl_crystal_density_diffrn 1.585 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_description block _exptl_crystal_F_000 344 _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.19 _refine_diff_density_max 0.331 _refine_diff_density_min -0.290 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.089 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 100 _refine_ls_number_reflns 1855 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.089 _refine_ls_R_factor_all 0.0383 _refine_ls_R_factor_gt 0.0301 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.08P)^2^] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1016 _refine_ls_wR_factor_ref 0.1073 _reflns_number_gt 1618 _reflns_number_total 1855 _reflns_threshold_expression I>2\s(I) loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,1/2+y,1/2-z -x,-y,-z x,1/2-y,1/2+z 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 S1 0.0166(2) 0.0118(2) 0.0205(2) 0.00120(10) -0.00220(10) -0.00100(10) O1 0.0122(5) 0.0111(4) 0.0138(4) 0.0003(3) 0.0009(3) -0.0003(3) O2 0.0170(5) 0.0156(5) 0.0166(5) 0.0045(4) 0.0005(4) 0.0007(3) N1 0.0127(5) 0.0115(5) 0.0177(5) -0.0017(4) 0.0005(4) -0.0008(4) N2 0.0147(5) 0.0131(5) 0.0178(6) 0.0010(4) 0.0014(4) 0.0000(4) C1 0.0154(6) 0.0131(6) 0.0101(6) -0.0023(5) 0.0033(4) -0.0004(4) C2 0.0119(6) 0.0149(6) 0.0093(6) 0.0005(4) 0.0028(4) 0.0003(4) C3 0.0122(6) 0.0140(6) 0.0110(6) 0.0026(4) 0.0032(5) 0.0016(4) C4 0.0160(7) 0.0171(6) 0.0140(6) -0.0020(5) 0.0034(5) -0.0003(5) C5 0.0279(7) 0.0150(6) 0.0197(7) -0.0042(5) 0.0098(6) -0.0023(5) C6 0.0288(8) 0.0136(6) 0.0196(7) 0.0060(5) 0.0079(6) 0.0030(5) loop_ _atom_site_label _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_refinement_flags _atom_site_occupancy _atom_site_type_symbol S1 0.12856(6) 0.471800(10) 0.27058(5) 0.01730(10) Uani . . 1.000 S O1 0.25400(16) 0.34259(4) 0.30831(13) 0.0127(3) Uani . . 1.000 O O2 0.67037(18) 0.19945(5) 0.47082(13) 0.0169(3) Uani . . 1.000 O N1 0.5789(2) 0.40572(5) 0.44103(15) 0.0144(3) Uani . . 1.000 N N2 0.6744(2) 0.34169(5) 0.47497(16) 0.0155(3) Uani . . 1.000 N C1 0.3276(3) 0.40781(6) 0.34354(18) 0.0128(3) Uani . . 1.000 C C2 0.4738(2) 0.30573(6) 0.39286(17) 0.0120(3) Uani . . 1.000 C C3 0.4506(2) 0.23451(6) 0.38206(18) 0.0123(3) Uani . . 1.000 C C4 0.2480(3) 0.19344(6) 0.30458(18) 0.0157(4) Uani . . 1.000 C C5 0.3477(3) 0.12750(7) 0.3467(2) 0.0202(4) Uani . . 1.000 C C6 0.6001(3) 0.13386(7) 0.44587(19) 0.0203(4) Uani . . 1.000 C H1 0.67190 0.44060 0.47890 0.0170 Uiso calc R 1.000 H H4 0.07920 0.20560 0.23790 0.0190 Uiso calc R 1.000 H H5 0.25610 0.08800 0.31240 0.0240 Uiso calc R 1.000 H H6 0.71190 0.09840 0.49130 0.0240 Uiso calc R 1.000 H loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source S S 0.1246 0.1234 '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' N N 0.0061 0.0033 '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' C C 0.0033 0.0016 '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 C1 O1 C2 105.37(10) yes C3 O2 C6 105.43(10) yes N2 N1 C1 113.03(10) yes N1 N2 C2 102.77(10) yes C1 N1 H1 123.50 no N2 N1 H1 123.46 no S1 C1 N1 130.93(10) yes S1 C1 O1 123.77(11) yes O1 C1 N1 105.30(10) yes O1 C2 C3 117.43(10) yes O1 C2 N2 113.52(10) yes N2 C2 C3 129.04(11) yes O2 C3 C4 111.37(11) yes C2 C3 C4 132.65(11) no O2 C3 C2 115.95(10) yes C3 C4 C5 105.61(12) no C4 C5 C6 106.56(13) no O2 C6 C5 111.03(12) yes C3 C4 H4 127.15 no C5 C4 H4 127.24 no C4 C5 H5 126.69 no C6 C5 H5 126.76 no O2 C6 H6 124.47 no C5 C6 H6 124.50 no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag S1 C1 1.659(2) yes O1 C1 1.373(2) yes O1 C2 1.3797(19) yes O2 C3 1.368(2) yes O2 C6 1.369(2) yes N1 N2 1.381(2) yes N1 C1 1.333(2) yes N2 C2 1.293(2) yes N1 H1 0.8593 no C2 C3 1.437(2) no C3 C4 1.353(2) no C4 C5 1.430(2) no C5 C6 1.347(3) no C4 H4 0.9301 no C5 H5 0.9295 no C6 H6 0.9298 no loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_2 _geom_contact_publ_flag S1 N1 3.321(3) 3_666 no S1 H1 3.0953 1_455 no S1 H5 3.0460 2_555 no S1 H1 2.5285 3_666 no S1 H6 2.9299 4_454 no O1 N2 2.236(3) . no O1 C5 3.385(4) 4_554 no O2 C2 3.296(3) 4_555 no O2 N2 2.860(3) . no O1 H4 2.9073 . no N1 O1 2.151(2) . no N1 S1 3.321(3) 3_666 no N1 C5 3.350(4) 4_555 no N2 O1 2.236(3) . no N2 O2 2.860(3) . no N2 C4 3.408(4) 4_655 no N2 C5 3.430(4) 4_555 no N2 C6 3.397(4) 4_555 no N2 H4 2.6391 4_655 no C1 C5 3.531(4) 4_554 no C1 C5 3.530(4) 4_555 no C1 C6 3.458(4) 4_554 no C2 O2 3.296(3) 4_554 no C2 C3 3.600(4) 4_554 no C2 C3 3.505(4) 4_555 no C2 C4 3.306(4) 4_555 no C2 C6 3.513(4) 4_554 no C3 C2 3.505(4) 4_554 no C3 C2 3.600(4) 4_555 no C3 C3 3.513(4) 4_554 no C3 C3 3.513(4) 4_555 no C4 N2 3.408(4) 4_454 no C4 C2 3.306(4) 4_554 no C5 O1 3.385(4) 4_555 no C5 N1 3.350(4) 4_554 no C5 N2 3.430(4) 4_554 no C5 C1 3.530(4) 4_554 no C5 C1 3.531(4) 4_555 no C6 N2 3.397(4) 4_554 no C6 C1 3.458(4) 4_555 no C6 C2 3.513(4) 4_555 no H1 S1 3.0953 1_655 no H1 S1 2.5286 3_666 no H4 O1 2.9073 . no H4 N2 2.6391 4_454 no H5 S1 3.0460 2_545 no H6 S1 2.9299 4_655 no 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 N1 H1 S1 3_666 0.86 2.53 3.321(3) 154 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 O1 C2 C3 178.58(10) no C2 O1 C1 S1 -179.76(10) no C2 O1 C1 N1 0.81(12) no C1 O1 C2 N2 -0.40(13) no C6 O2 C3 C4 0.32(14) no C3 O2 C6 C5 -0.21(14) no C6 O2 C3 C2 178.61(10) no N2 N1 C1 S1 179.64(10) no C1 N1 N2 C2 0.73(13) no N2 N1 C1 O1 -0.98(14) no N1 N2 C2 C3 -179.00(12) no N1 N2 C2 O1 -0.17(13) no O1 C2 C3 C4 -0.9(2) no O1 C2 C3 O2 -178.71(10) no N2 C2 C3 O2 0.08(19) no N2 C2 C3 C4 177.91(14) no C2 C3 C4 C5 -178.21(13) no O2 C3 C4 C5 -0.31(14) no C3 C4 C5 C6 0.17(15) no C4 C5 C6 O2 0.03(17) no