#------------------------------------------------------------------------------ #$Date: 2008-03-30 11:21:05 +0100 (Sun, 30 Mar 2008) $ #$Revision: 321 $ #$URL: svn://www.crystallography.net/cod/cif/2/2204306.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_2204306 loop_ _publ_author_name 'Dege, Necmi' '\,Cetin, Ahmet' 'Cans\?iz, Ahmet' '\,Sekerci, Memet' 'Cavit, Kazaz' 'Din\,cer, Muharrem' 'B\"uy\"ukg\"ung\"or, Orhan' _publ_section_title ; 4-Benzyl-3-(2-hydroxyphenyl)-1H-1,2,4-triazole-5(4H)-thione ; _journal_issue 10 _journal_name_full 'Acta Crystallographica, Section E' _journal_page_first o1883 _journal_page_last o1885 _journal_volume 60 _journal_year 2004 _chemical_formula_iupac 'C15 H13 N3 O1 S1' _chemical_formula_moiety 'C15 H13 N3 O1 S1' _chemical_formula_structural 'C15 H13 N3 O1 S1' _chemical_formula_sum 'C15 H13 N3 O1 S1' _chemical_formula_weight 283.34 _chemical_name_systematic ; 4-Benzyl-3-(2-hydroxyphenyl)-1H-1,2,4-triazole-5(4H)-thione ; _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 21/n' _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 104.655(7) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 5.7387(5) _cell_length_b 23.842(3) _cell_length_c 10.3045(9) _cell_measurement_reflns_used 5446 _cell_measurement_temperature 296 _cell_measurement_theta_max 26.04 _cell_measurement_theta_min 1.71 _cell_volume 1364.0(2) _computing_cell_refinement X-AREA _computing_data_collection 'X-AREA (Stoe & Cie, 2002)' _computing_data_reduction 'X-RED32 (Stoe & Cie, 2002)' _computing_molecular_graphics 'ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 1997)' _computing_publication_material 'WinGX (Farrugia, 1999)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 296 _diffrn_detector_area_resol_mean 6.67 _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.996 _diffrn_measurement_device '2-circle goniometer' _diffrn_measurement_device_type 'Stoe IPDS-2' _diffrn_measurement_method \w _diffrn_radiation_monochromator 'plane graphite' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0776 _diffrn_reflns_av_sigmaI/netI 0.0701 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 29 _diffrn_reflns_limit_k_min -29 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 7312 _diffrn_reflns_theta_full 26.05 _diffrn_reflns_theta_max 26.05 _diffrn_reflns_theta_min 1.71 _diffrn_standards_decay_% 0 _diffrn_standards_interval_count 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.236 _exptl_absorpt_correction_T_max 0.9875 _exptl_absorpt_correction_T_min 0.8593 _exptl_absorpt_correction_type integration _exptl_absorpt_process_details '(X-RED32; Stoe & Cie, 2002)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.380 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 592 _exptl_crystal_size_max 0.740 _exptl_crystal_size_mid 0.427 _exptl_crystal_size_min 0.050 _refine_diff_density_max 0.162 _refine_diff_density_min -0.257 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.870 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 181 _refine_ls_number_reflns 2673 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.870 _refine_ls_R_factor_all 0.0667 _refine_ls_R_factor_gt 0.0435 _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^)+(0.0654P)^2^] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1014 _refine_ls_wR_factor_ref 0.1087 _reflns_number_gt 1737 _reflns_number_total 2673 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file ci6452.cif loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' 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_ _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 S1 1.36193(10) -0.02084(2) 0.17678(6) 0.05650(18) Uani d . 1 S O1 0.8270(4) 0.18499(8) -0.17450(19) 0.0874(6) Uani d . 1 O H1 0.9308 0.1605 -0.1613 0.131 Uiso calc R 1 H N1 1.0596(3) 0.06973(7) 0.14217(16) 0.0472(4) Uani d . 1 N N2 1.1363(3) 0.11347(7) -0.03084(17) 0.0531(4) Uani d . 1 N N3 1.2742(3) 0.06623(7) 0.00063(16) 0.0517(4) Uani d . 1 N H3 1.3765 0.0556 -0.0426 0.062 Uiso calc R 1 H C1 0.7406(4) 0.19044(9) -0.0643(3) 0.0653(6) Uani d . 1 C C2 0.5610(5) 0.22983(11) -0.0708(3) 0.0823(8) Uani d . 1 C H2 0.5036 0.2502 -0.1494 0.099 Uiso calc R 1 H C3 0.4662(5) 0.23930(11) 0.0369(4) 0.0851(8) Uani d . 1 C H3A 0.3450 0.2658 0.0305 0.102 Uiso calc R 1 H C4 0.5492(5) 0.20992(11) 0.1536(3) 0.0757(7) Uani d . 1 C H4 0.4867 0.2169 0.2269 0.091 Uiso calc R 1 H C5 0.7257(4) 0.17008(10) 0.1616(2) 0.0657(6) Uani d . 1 C H5 0.7812 0.1503 0.2411 0.079 Uiso calc R 1 H C6 0.8244(4) 0.15849(8) 0.0527(2) 0.0531(5) Uani d . 1 C C7 1.0053(4) 0.11520(8) 0.0561(2) 0.0482(5) Uani d . 1 C C8 1.2340(3) 0.03832(8) 0.10510(19) 0.0466(5) Uani d . 1 C C9 0.9526(4) 0.05143(9) 0.2495(2) 0.0540(5) Uani d . 1 C H9A 0.9715 0.0111 0.2596 0.065 Uiso calc R 1 H H9B 0.7813 0.0594 0.2232 0.065 Uiso calc R 1 H C10 1.0586(3) 0.07848(8) 0.3829(2) 0.0494(5) Uani d . 1 C C11 1.2717(4) 0.10784(10) 0.4115(2) 0.0621(6) Uani d . 1 C H11 1.3554 0.1122 0.3458 0.075 Uiso calc R 1 H C12 1.3628(4) 0.13096(12) 0.5378(2) 0.0725(7) Uani d . 1 C H12 1.5071 0.1508 0.5562 0.087 Uiso calc R 1 H C13 1.2414(5) 0.12471(11) 0.6350(2) 0.0699(7) Uani d . 1 C H13 1.3022 0.1405 0.7193 0.084 Uiso calc R 1 H C14 1.0306(5) 0.09525(10) 0.6082(2) 0.0691(7) Uani d . 1 C H14 0.9488 0.0906 0.6748 0.083 Uiso calc R 1 H C15 0.9384(4) 0.07232(9) 0.4828(2) 0.0618(6) Uani d . 1 C H15 0.7941 0.0525 0.4652 0.074 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 S1 0.0555(3) 0.0550(3) 0.0632(3) 0.0036(2) 0.0228(3) 0.0052(3) O1 0.1073(14) 0.0805(12) 0.0785(12) 0.0197(10) 0.0314(11) 0.0242(9) N1 0.0463(9) 0.0499(9) 0.0463(9) -0.0025(7) 0.0136(7) -0.0046(7) N2 0.0575(10) 0.0511(10) 0.0507(10) -0.0003(8) 0.0138(8) -0.0022(8) N3 0.0542(10) 0.0531(10) 0.0519(10) 0.0012(8) 0.0214(8) -0.0015(8) C1 0.0695(15) 0.0505(12) 0.0729(15) -0.0024(11) 0.0126(12) -0.0005(11) C2 0.0838(18) 0.0564(14) 0.098(2) 0.0136(13) 0.0076(16) 0.0070(14) C3 0.0714(16) 0.0565(15) 0.121(3) 0.0122(13) 0.0120(18) -0.0142(16) C4 0.0685(15) 0.0700(16) 0.0871(18) 0.0105(13) 0.0172(14) -0.0224(14) C5 0.0645(14) 0.0654(14) 0.0639(14) 0.0061(11) 0.0098(11) -0.0158(11) C6 0.0508(11) 0.0478(11) 0.0567(12) -0.0016(9) 0.0063(10) -0.0096(9) C7 0.0477(11) 0.0478(11) 0.0468(10) -0.0041(9) 0.0075(9) -0.0044(9) C8 0.0428(10) 0.0502(11) 0.0474(11) -0.0050(8) 0.0125(9) -0.0075(9) C9 0.0492(11) 0.0569(12) 0.0608(13) -0.0059(10) 0.0230(10) -0.0041(10) C10 0.0499(11) 0.0522(11) 0.0490(11) 0.0042(9) 0.0180(10) 0.0036(9) C11 0.0550(12) 0.0807(15) 0.0531(12) -0.0091(11) 0.0182(10) -0.0047(11) C12 0.0610(14) 0.0908(18) 0.0628(14) -0.0101(13) 0.0102(12) -0.0116(13) C13 0.0875(18) 0.0724(15) 0.0487(12) 0.0118(14) 0.0149(12) -0.0020(11) C14 0.0949(18) 0.0655(14) 0.0571(14) 0.0065(13) 0.0381(13) 0.0036(11) C15 0.0641(13) 0.0622(13) 0.0662(14) -0.0027(11) 0.0298(12) -0.0007(11) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag S1 C8 1.673(2) yes O1 C1 1.355(3) yes O1 H1 0.82 ? N1 C8 1.379(2) yes N1 C7 1.385(2) yes N1 C9 1.461(2) yes N2 C7 1.308(2) yes N2 N3 1.368(2) yes N3 C8 1.334(2) yes N3 H3 0.86 ? C1 C2 1.383(3) ? C1 C6 1.404(3) ? C2 C3 1.372(4) ? C2 H2 0.93 ? C3 C4 1.369(4) ? C3 H3A 0.93 ? C4 C5 1.376(3) ? C4 H4 0.93 ? C5 C6 1.407(3) ? C5 H5 0.93 ? C6 C7 1.458(3) yes C9 C10 1.500(3) yes C9 H9A 0.97 ? C9 H9B 0.97 ? C10 C11 1.375(3) ? C10 C15 1.384(3) ? C11 C12 1.388(3) ? C11 H11 0.93 ? C12 C13 1.366(3) ? C12 H12 0.93 ? C13 C14 1.365(4) ? C13 H13 0.93 ? C14 C15 1.380(3) ? C14 H14 0.93 ? C15 H15 0.93 ? 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 H1 109.5 yes C8 N1 C7 108.02(15) ? C8 N1 C9 121.40(16) yes C7 N1 C9 130.44(16) yes C7 N2 N3 105.19(16) ? C8 N3 N2 113.21(15) ? C8 N3 H3 123.4 ? N2 N3 H3 123.4 ? O1 C1 C2 116.8(2) yes O1 C1 C6 123.3(2) yes C2 C1 C6 119.9(2) ? C3 C2 C1 121.0(3) ? C3 C2 H2 119.5 ? C1 C2 H2 119.5 ? C4 C3 C2 120.3(2) ? C4 C3 H3A 119.8 ? C2 C3 H3A 119.8 ? C3 C4 C5 119.6(3) ? C3 C4 H4 120.2 ? C5 C4 H4 120.2 ? C4 C5 C6 121.8(2) ? C4 C5 H5 119.1 ? C6 C5 H5 119.1 ? C1 C6 C5 117.3(2) ? C1 C6 C7 119.48(19) yes C5 C6 C7 123.2(2) yes N2 C7 N1 109.79(17) ? N2 C7 C6 122.33(18) yes N1 C7 C6 127.83(17) ? N3 C8 N1 103.79(17) ? N3 C8 S1 129.07(15) yes N1 C8 S1 127.13(15) yes N1 C9 C10 114.47(16) yes N1 C9 H9A 108.6 ? C10 C9 H9A 108.6 ? N1 C9 H9B 108.6 ? C10 C9 H9B 108.6 ? H9A C9 H9B 107.6 ? C11 C10 C15 118.57(19) ? C11 C10 C9 123.22(17) ? C15 C10 C9 118.19(18) ? C10 C11 C12 120.5(2) ? C10 C11 H11 119.8 ? C12 C11 H11 119.8 ? C13 C12 C11 120.2(2) ? C13 C12 H12 119.9 ? C11 C12 H12 119.9 ? C14 C13 C12 119.9(2) ? C14 C13 H13 120.1 ? C12 C13 H13 120.1 ? C13 C14 C15 120.2(2) ? C13 C14 H14 119.9 ? C15 C14 H14 119.9 ? C14 C15 C10 120.6(2) ? C14 C15 H15 119.7 ? C10 C15 H15 119.7 ? 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 C7 N2 N3 C8 -0.2(2) yes O1 C1 C2 C3 -178.4(2) ? C6 C1 C2 C3 1.5(4) ? C1 C2 C3 C4 0.3(4) ? C2 C3 C4 C5 -1.1(4) ? C3 C4 C5 C6 0.0(4) ? O1 C1 C6 C5 177.5(2) ? C2 C1 C6 C5 -2.5(3) ? O1 C1 C6 C7 -3.0(3) yes C2 C1 C6 C7 177.0(2) ? C4 C5 C6 C1 1.8(3) ? C4 C5 C6 C7 -177.8(2) ? N3 N2 C7 N1 0.2(2) ? N3 N2 C7 C6 -177.20(17) ? C8 N1 C7 N2 -0.2(2) ? C9 N1 C7 N2 -175.77(18) ? C8 N1 C7 C6 177.05(19) ? C9 N1 C7 C6 1.4(3) yes C1 C6 C7 N2 17.1(3) yes C5 C6 C7 N2 -163.3(2) ? C1 C6 C7 N1 -159.7(2) ? C5 C6 C7 N1 19.8(3) yes N2 N3 C8 N1 0.1(2) ? N2 N3 C8 S1 -179.86(15) ? C7 N1 C8 N3 0.0(2) ? C9 N1 C8 N3 176.14(16) ? C7 N1 C8 S1 179.98(15) ? C9 N1 C8 S1 -3.9(3) yes C8 N1 C9 C10 98.6(2) yes C7 N1 C9 C10 -86.2(3) yes N1 C9 C10 C11 -14.2(3) yes N1 C9 C10 C15 167.40(18) ? C15 C10 C11 C12 -0.3(3) ? C9 C10 C11 C12 -178.7(2) ? C10 C11 C12 C13 0.0(4) ? C11 C12 C13 C14 0.5(4) ? C12 C13 C14 C15 -0.7(4) ? C13 C14 C15 C10 0.5(4) ? C11 C10 C15 C14 0.1(3) ? C9 C10 C15 C14 178.5(2) ? 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 N3 H3 S1 3_855 0.86 2.43 3.287(2) 175 O1 H1 N2 . 0.82 1.91 2.631(3) 146