#------------------------------------------------------------------------------ #$Date: 2015-04-02 12:22:18 +0100 (Thu, 02 Apr 2015) $ #$Revision: 134621 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/84/2008450.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_2008450 loop_ _publ_author_name 'Billodeaux, Damon R.' 'Fronczek, Frank R.' 'D\"ur\"u\,st, Ya\;sar' _publ_section_title ; Two novel 3,4-disubstituted 1,2,4-oxadiazole-5(4H)-thiones ; _journal_issue 5 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 761 _journal_page_last 764 _journal_paper_doi 10.1107/S0108270199000475 _journal_volume 55 _journal_year 1999 _chemical_formula_moiety C10H11N3OS _chemical_formula_sum 'C10 H11 N3 O S' _chemical_formula_weight 221.28 _chemical_melting_point 337.5(5) _chemical_name_systematic ; 3-(2-pyridyl)-4-n-propyl-1,2,4-oxadiazoline-5-thione ; _space_group_IT_number 2 _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _cell_angle_alpha 112.890(10) _cell_angle_beta 112.029(9) _cell_angle_gamma 94.840(10) _cell_formula_units_Z 2 _cell_length_a 7.7280(10) _cell_length_b 8.826(2) _cell_length_c 9.3699(9) _cell_measurement_reflns_used 25 _cell_measurement_temperature 100 _cell_measurement_theta_max 18.2 _cell_measurement_theta_min 11.6 _cell_volume 525.57(16) _computing_cell_refinement 'CAD4 EXPRESS' _computing_data_collection 'CAD4 EXPRESS (Enraf-Nonius, 1993)' _computing_data_reduction 'PROCESS in MolEN (Fair, 1990)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material 'CIF IN in MolEN' _computing_structure_refinement 'LSFM in MolEN' _computing_structure_solution 'Direct methods (SIR; Burla et al., 1989)' _diffrn_ambient_temperature 100 _diffrn_measurement_device Enraf_Nonius_CAD4 _diffrn_measurement_method \q/2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source sealed_tube _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.012 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 5166 _diffrn_reflns_theta_max 30.0 _diffrn_reflns_theta_min 2.5 _diffrn_standards_decay_% 0.1 _diffrn_standards_interval_time 60 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.271 _exptl_absorpt_correction_T_max 0.92 _exptl_absorpt_correction_T_min 0.88 _exptl_absorpt_correction_type '\y scans (North et al., 1968)' _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.399 _exptl_crystal_density_method none _exptl_crystal_description fragment _exptl_crystal_F_000 232 _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.42 _exptl_crystal_size_min 0.30 _refine_diff_density_max 0.53 _refine_diff_density_min -0.49 _refine_ls_abs_structure_details ' ?' _refine_ls_extinction_method none _refine_ls_goodness_of_fit_obs 1.955 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_constraints 0 _refine_ls_number_parameters 180 _refine_ls_number_reflns 2753 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.050 _refine_ls_R_factor_obs .044 _refine_ls_shift/esd_max 0.017 _refine_ls_shift/esd_mean 0.003 _refine_ls_structure_factor_coef F _refine_ls_weighting_details 'w = 4Fo^2^/(\s^2^(Fo^2^) + 0.0004 Fo^4^)' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all 0.058 _refine_ls_wR_factor_obs .058 _reflns_number_observed 2753 _reflns_number_total 3063 _reflns_observed_criterion >1.0\s(I) _[local]_cod_data_source_file da1041.cif _[local]_cod_data_source_block 2 _[local]_cod_cif_authors_sg_H-M P-1 _[local]_cod_chemical_formula_sum_orig C10H11N3OS _cod_depositor_comments ; The following automatic conversions were performed: '_chemical_melting_point' value '337-338 K' was changed to '337.5(5)' - the average value was taken and precision was estimated. '_atom_site_thermal_displace_type' tag value 'Uij' was replaced with 'Uani' value 15 times. Automatic conversion script Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana The following automatic conversions were performed: '_chemical_melting_point' value '337-338 K' was changed to '337.5(5)' - the average value was taken and precision was estimated. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana The following automatic conversions were performed: '_refine_ls_weighting_scheme' value '4Fo^2^/(\s^2^(Fo^2^) + 0.0004 Fo^4^)' was changed to 'calc'. New tag '_refine_ls_weighting_details' was created. The value of the new tag was set to 'w = 4Fo^2^/(\s^2^(Fo^2^) + 0.0004 Fo^4^)'. Automatic conversion script Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas ; _cod_original_cell_volume 525.6(4) _cod_database_code 2008450 loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-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 _atom_site_aniso_type_symbol S .02240(10) .01910(10) .02480(10) .00180(10) .00750(10) .00880(10) S O1 .0212(4) .0139(3) .0228(4) .0039(3) .0063(3) .0098(3) O N2 .0214(5) .0140(4) .0204(4) .0023(4) .0055(4) .0070(3) N N4 .0161(4) .0139(4) .0180(4) .0035(4) .0064(3) .0080(3) N N7 .0232(5) .0145(4) .0211(4) .0036(4) .0074(4) .0086(3) N C3 .0168(5) .0148(4) .0147(4) .0022(4) .0078(3) .0066(3) C C5 .0194(5) .0152(5) .0207(4) .0042(4) .0105(4) .0094(3) C C6 .0188(5) .0143(5) .0148(4) .0038(4) .0092(3) .0063(3) C C8 .0296(6) .0167(5) .0246(5) .0069(5) .0105(4) .0111(4) C C9 .0330(6) .0138(5) .0217(5) .0013(5) .0141(4) .0041(4) C C10 .0241(6) .0194(6) .0170(5) -.0003(5) .0076(4) .0020(4) C C11 .0205(5) .0196(5) .0160(4) .0041(5) .0069(4) .0066(4) C C12 .0159(5) .0178(5) .0199(4) .0045(4) .0073(4) .0096(3) C C13 .0224(6) .0191(5) .0200(5) .0054(5) .0101(4) .0089(4) C C14 .0294(6) .0271(6) .0217(5) .0111(5) .0109(4) .0131(4) C 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_calc_attached_atom _atom_site_type_symbol S .72448(6) 1.10791(5) .96876(5) .02200(10) Uani ? ? S O1 .3956(2) .90370(10) .70540(10) .0189(4) Uani ? ? O N2 .2934(2) .72790(10) .6032(2) .0183(4) Uani ? ? N N4 .5816(2) .76200(10) .80690(10) .0159(4) Uani ? ? N N7 .4790(2) .39260(10) .67870(10) .0192(4) Uani ? ? N C3 .4093(2) .6496(2) .6692(2) .0154(4) Uani ? ? C C5 .5692(2) .9218(2) .8291(2) .0183(5) Uani ? ? C C6 .3536(2) .4622(2) .5975(2) .0159(4) Uani ? ? C C8 .4279(2) .2230(2) .6157(2) .0230(5) Uani ? ? C C9 .2542(2) .1177(2) .4734(2) .0214(5) Uani ? ? C C10 .1272(2) .1911(2) .3909(2) .0199(6) Uani ? ? C C11 .1764(2) .3661(2) .4526(2) .0186(5) Uani ? ? C C12 .7529(2) .7273(2) .9147(2) .0178(5) Uani ? ? C C13 .7343(2) .7146(2) 1.0655(2) .0204(5) Uani ? ? C C14 .8965(2) .6478(2) 1.1534(2) .0259(6) Uani ? ? C H8 .512(3) .178(2) .670(2) .036(6) Uiso ? ? H H9 .224(3) -.002(2) .438(2) .028(5) Uiso ? ? H H10 .012(3) .125(2) .296(2) .033(6) Uiso ? ? H H11 .101(3) .423(2) .400(2) .036(6) Uiso ? ? H H12a .865(3) .821(2) .956(2) .030(6) Uiso ? ? H H12b .774(2) .621(2) .840(2) .024(5) Uiso ? ? H H13b .613(3) .639(2) 1.025(2) .029(5) Uiso ? ? H H13a .739(3) .826(3) 1.150(2) .040(6) Uiso ? ? H H14b .908(3) .656(2) 1.267(2) .035(6) Uiso ? ? H H14c .885(3) .542(3) 1.086(2) .042(7) Uiso ? ? H H14a 1.014(3) .708(2) 1.181(2) .032(6) Uiso ? ? H loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C 0.002 0.002 International_Tables_Vol_IV_Table_2.3.1 H 0.000 0.000 International_Tables_Vol_IV_Table_2.3.1 N 0.004 0.003 International_Tables_Vol_IV_Table_2.3.1 O 0.008 0.006 International_Tables_Vol_IV_Table_2.3.1 S 0.110 0.124 International_Tables_Vol_IV_Table_2.3.1 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 1 4 0 -5 5 -2 4 2 -8 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 N2 O1 C5 109.70(10) yes O1 N2 C3 104.60(9) yes C3 N4 C5 106.80(10) yes C3 N4 C12 129.80(10) ? C5 N4 C12 123.45(9) ? C6 N7 C8 117.10(10) ? N2 C3 N4 112.00(10) yes N2 C3 C6 121.00(10) ? N4 C3 C6 127.00(10) ? S C5 O1 122.50(10) ? S C5 N4 130.60(10) ? O1 C5 N4 106.86(9) yes N7 C6 C3 116.90(10) ? N7 C6 C11 123.30(10) ? C3 C6 C11 119.80(10) ? N7 C8 C9 123.6(2) ? N7 C8 H8 116.0(10) ? C9 C8 H8 120.0(10) ? C8 C9 C10 118.60(10) ? C8 C9 H9 119.0(10) ? C10 C9 H9 121.0(10) ? C9 C10 C11 119.20(10) ? C9 C10 H10 120.0(10) ? C11 C10 H10 120.0(10) ? C6 C11 C10 118.20(10) ? C6 C11 H11 118.0(10) ? C10 C11 H11 123.5(9) ? N4 C12 C13 112.20(10) ? N4 C12 H12a 106.0(10) ? N4 C12 H12b 109.0(10) ? C13 C12 H12a 111.0(10) ? C13 C12 H12b 111.0(10) ? H12a C12 H12b 106.0(10) ? C12 C13 C14 110.10(10) ? C12 C13 H13b 109.0(10) ? C12 C13 H13a 110.0(10) ? C14 C13 H13b 109.0(10) ? C14 C13 H13a 109.0(10) ? H13b C13 H13a 107.0(10) ? C13 C14 H14b 114.0(10) ? C13 C14 H14c 111.0(10) ? C13 C14 H14a 112.0(10) ? H14b C14 H14c 108(2) ? H14b C14 H14a 103.0(10) ? H14c C14 H14a 106(2) ? 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 S C5 . . 1.6340(10) yes O1 N2 . . 1.4210(10) yes O1 C5 . . 1.350(2) yes N2 C3 . . 1.298(2) yes N4 C3 . . 1.3840(10) yes N4 C5 . . 1.360(2) yes N4 C12 . . 1.474(2) ? N7 C6 . . 1.344(2) ? N7 C8 . . 1.335(2) ? C3 C6 . . 1.473(2) yes C6 C11 . . 1.397(2) ? C8 C9 . . 1.388(2) ? C8 H8 . . .89(2) ? C9 C10 . . 1.381(3) ? C9 H9 . . .95(2) ? C10 C11 . . 1.380(2) ? C10 H10 . . .920(10) ? C11 H11 . . .93(2) ? C12 C13 . . 1.517(3) ? C12 H12a . . .99(2) ? C12 H12b . . 1.00(2) ? C13 C14 . . 1.525(2) ? C13 H13b . . .95(2) ? C13 H13a . . .98(2) ? C14 H14b . . 1.01(2) ? C14 H14c . . .87(2) ? C14 H14a . . .90(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 C5 O1 N2 C3 -0.2(2) ? N2 O1 C5 S 179.60(10) ? N2 O1 C5 N4 0.9(2) ? O1 N2 C3 N4 -0.6(2) ? O1 N2 C3 C6 179.80(10) ? C5 N4 C3 N2 1.1(2) ? C5 N4 C3 C6 -179.30(10) ? C12 N4 C3 N2 -178.40(10) ? C12 N4 C3 C6 1.1(2) yes C3 N4 C5 S -179.70(10) ? C3 N4 C5 O1 -1.2(2) ? C12 N4 C5 S -0.1(2) yes C12 N4 C5 O1 178.40(10) ? C3 N4 C12 C13 -86.6(2) yes C5 N4 C12 C13 93.9(2) ? C8 N7 C6 C3 179.10(10) ? C8 N7 C6 C11 -0.3(2) ? C6 N7 C8 C9 -0.3(2) ? N2 C3 C6 N7 -177.10(10) ? N2 C3 C6 C11 2.3(2) ? N4 C3 C6 N7 3.3(2) yes N4 C3 C6 C11 -177.30(10) ? N7 C6 C11 C10 0.6(2) ? C3 C6 C11 C10 -178.70(10) ? N7 C8 C9 C10 0.5(3) ? C8 C9 C10 C11 -0.2(3) ? C9 C10 C11 C6 -0.4(2) ? N4 C12 C13 C14 170.00(10) yes