#------------------------------------------------------------------------------ #$Date: 2008-01-13 22:15:36 +0000 (Sun, 13 Jan 2008) $ #$Revision: 14 $ #$URL: svn://www.crystallography.net/cod/cif/2/2203359.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # 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_structural ? _chemical_formula_sum 'C6 H4 N2 O2 S' _chemical_formula_weight 168.18 _chemical_melting_point ? _chemical_name_common ? _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_decay_% ? _diffrn_standards_interval_count . _diffrn_standards_interval_time . _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_meas ? _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 _exptl_crystal_size_rad ? _refine_diff_density_max 0.331 _refine_diff_density_min -0.290 _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? _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_constraints ? _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_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l ? ? ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_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_site_symmetry_1 _geom_bond_site_symmetry_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_1 _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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_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