data_2203280
loop_
_publ_author_name
'Sema \"Ozt\"urk'
'Mehmet Akkurt'
'Ahmet Cans\?iz'
'Metin Kopar\?ir'
'Mehmet \,Sekerci'
'Frank W. Heinemann'
_publ_section_title
;
4-(4-Chlorophenyl)-3-(furan-2-yl)-1H-1,2,4-triazole-5(4H)-thione
;
_journal_issue                 3
_journal_name_full             'Acta Crystallographica, Section E'
_journal_page_first            o425
_journal_page_last             o427
_journal_volume                60
_journal_year                  2004
_chemical_formula_iupac        'C12 H8 Cl N3 O S'
_chemical_formula_moiety       'C12 H8 Cl N3 O S'
_chemical_formula_structural   ?
_chemical_formula_sum          'C12 H8 Cl N3 O S'
_chemical_formula_weight       277.73
_chemical_melting_point        ?
_chemical_name_common          ?
_chemical_name_systematic
;
4-(4-Chlorophenyl)-3-(furan-2-yl)-1H-1,2,4-triazole-5(4H)-thione
;
_symmetry_cell_setting         Triclinic
_symmetry_space_group_name_Hall '-P 1'
_symmetry_space_group_name_H-M 'P -1'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary   direct
_atom_sites_solution_secondary difmap
_cell_angle_alpha              91.426(5)
_cell_angle_beta               90.250(5)
_cell_angle_gamma              116.059(5)
_cell_formula_units_Z          2
_cell_length_a                 8.524(5)
_cell_length_b                 8.640(5)
_cell_length_c                 9.307(5)
_cell_measurement_reflns_used  78
_cell_measurement_temperature  100
_cell_measurement_theta_max    20
_cell_measurement_theta_min    6
_cell_volume                   615.5(6)
_computing_cell_refinement     'EvalCCD (Duisenberg, 2003)'
_computing_data_collection     'COLLECT (Nonius, 1999)'
_computing_data_reduction      EvalCCD
_computing_molecular_graphics  'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material 'WinGX (Farrugia, 1999)'
_computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution  'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature    100
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type 'Bruker--Nonius KappaCCD'
_diffrn_measurement_method
'\w scans (per frame) with 2.0\% and 80 s 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 0.0350
_diffrn_reflns_av_sigmaI/netI  0.0295
_diffrn_reflns_limit_h_max     11
_diffrn_reflns_limit_h_min     -11
_diffrn_reflns_limit_k_max     11
_diffrn_reflns_limit_k_min     -11
_diffrn_reflns_limit_l_max     12
_diffrn_reflns_limit_l_min     -12
_diffrn_reflns_number          17300
_diffrn_reflns_reduction_process ' ?'
_diffrn_reflns_theta_full      28.99
_diffrn_reflns_theta_max       28.99
_diffrn_reflns_theta_min       2.80
_diffrn_standards_decay_%      0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_number       0
_exptl_absorpt_coefficient_mu  0.469
_exptl_absorpt_correction_T_max 0.9679
_exptl_absorpt_correction_T_min 0.8997
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour          colorless
_exptl_crystal_density_diffrn  1.499
_exptl_crystal_density_meas    ?
_exptl_crystal_density_method  'Not Measured'
_exptl_crystal_description     prism
_exptl_crystal_F_000           284
_exptl_crystal_size_max        0.23
_exptl_crystal_size_mid        0.15
_exptl_crystal_size_min        0.07
_exptl_crystal_size_rad        ?
_refine_diff_density_max       0.433
_refine_diff_density_min       -0.344
_refine_ls_abs_structure_details ?
_refine_ls_abs_structure_Flack ?
_refine_ls_extinction_coef     0.012(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method   SHELXL97
_refine_ls_goodness_of_fit_ref 1.155
_refine_ls_hydrogen_treatment  constr
_refine_ls_matrix_type         full
_refine_ls_number_constraints  ?
_refine_ls_number_parameters   164
_refine_ls_number_reflns       3274
_refine_ls_number_restraints   0
_refine_ls_restrained_S_all    1.155
_refine_ls_R_factor_all        0.0484
_refine_ls_R_factor_gt         0.0332
_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^)+(0.053P)^2^+0.1559P] where P = (Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme    calc
_refine_ls_wR_factor_gt        0.0935
_refine_ls_wR_factor_ref       0.0983
_reflns_number_gt              2673
_reflns_number_total           3274
_reflns_threshold_expression   I>2\s(I)
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
Cl1 0.0151(2) 0.0280(2) 0.0246(2) 0.0108(2) -0.0075(2) 0.0046(2)
S1 0.0120(2) 0.0096(2) 0.0217(2) 0.0033(2) -0.0047(2) 0.00070(10)
O1 0.0111(5) 0.0112(5) 0.0219(6) 0.0018(4) -0.0036(5) 0.0023(4)
N1 0.0086(6) 0.0106(6) 0.0125(6) 0.0039(5) -0.0013(5) 0.0002(5)
N2 0.0109(6) 0.0097(6) 0.0165(7) 0.0049(5) -0.0019(5) 0.0018(5)
N3 0.0110(6) 0.0105(6) 0.0136(6) 0.0042(5) -0.0002(5) 0.0005(5)
C1 0.0115(7) 0.0131(7) 0.0120(7) 0.0067(6) -0.0002(6) -0.0005(6)
C2 0.0084(7) 0.0120(7) 0.0104(7) 0.0042(6) 0.0000(5) -0.0008(5)
C3 0.0087(7) 0.0111(7) 0.0112(7) 0.0028(6) 0.0001(5) -0.0002(6)
C4 0.0173(8) 0.0097(7) 0.0183(8) 0.0032(6) 0.0008(6) 0.0025(6)
C5 0.0193(8) 0.0134(7) 0.0158(8) 0.0078(7) 0.0028(6) 0.0038(6)
C6 0.0117(7) 0.0150(8) 0.0161(8) 0.0051(6) 0.0000(6) 0.0026(6)
C7 0.0084(7) 0.0095(7) 0.0144(7) 0.0035(6) -0.0013(6) 0.0023(6)
C8 0.0114(7) 0.0167(8) 0.0129(7) 0.0057(6) -0.0017(6) -0.0021(6)
C9 0.0113(7) 0.0176(8) 0.0175(8) 0.0076(6) 0.0001(6) -0.0005(6)
C10 0.0094(7) 0.0131(7) 0.0183(8) 0.0033(6) -0.0048(6) 0.0039(6)
C11 0.0187(8) 0.0176(8) 0.0125(8) 0.0071(7) -0.0041(6) -0.0010(6)
C12 0.0143(7) 0.0156(8) 0.0144(8) 0.0074(6) -0.0010(6) -0.0014(6)
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
Cl1 0.24926(5) 0.28710(6) 0.54297(5) 0.02210(10) Uani . . 1.000 Cl
S1 0.73723(5) -0.06080(5) 0.86255(4) 0.01500(10) Uani . . 1.000 S
O1 1.25470(15) 0.71668(15) 0.82711(13) 0.0158(3) Uani . . 1.000 O
N1 0.88284(17) 0.28469(17) 0.80635(14) 0.0107(3) Uani . . 1.000 N
N2 1.05521(17) 0.20964(17) 0.92167(14) 0.0122(4) Uani . . 1.000 N
N3 1.14754(17) 0.38461(17) 0.90714(14) 0.0119(3) Uani . . 1.000 N
C1 0.8929(2) 0.1433(2) 0.86417(17) 0.0118(4) Uani . . 1.000 C
C2 1.03994(19) 0.42718(19) 0.83586(16) 0.0104(4) Uani . . 1.000 C
C3 1.08480(19) 0.6018(2) 0.79432(16) 0.0109(4) Uani . . 1.000 C
C4 1.2724(2) 0.8746(2) 0.78527(18) 0.0161(4) Uani . . 1.000 C
C5 1.1205(2) 0.8616(2) 0.72812(17) 0.0159(4) Uani . . 1.000 C
C6 0.9981(2) 0.6844(2) 0.73417(17) 0.0145(4) Uani . . 1.000 C
C7 0.72759(19) 0.28256(19) 0.74118(17) 0.0109(4) Uani . . 1.000 C
C8 0.6261(2) 0.3385(2) 0.82327(17) 0.0139(4) Uani . . 1.000 C
C9 0.4795(2) 0.3427(2) 0.76078(18) 0.0150(4) Uani . . 1.000 C
C10 0.4369(2) 0.2865(2) 0.61864(18) 0.0142(4) Uani . . 1.000 C
C11 0.5365(2) 0.2285(2) 0.53635(18) 0.0166(5) Uani . . 1.000 C
C12 0.6855(2) 0.2277(2) 0.59868(17) 0.0145(4) Uani . . 1.000 C
H2 1.09730 0.14820 0.96360 0.0150 Uiso calc R 1.000 H
H4 1.37470 0.97660 0.79480 0.0190 Uiso calc R 1.000 H
H5 1.10010 0.95070 0.69200 0.0190 Uiso calc R 1.000 H
H6 0.88200 0.63520 0.70310 0.0170 Uiso calc R 1.000 H
H8 0.65570 0.37290 0.91900 0.0170 Uiso calc R 1.000 H
H9 0.41130 0.38240 0.81330 0.0180 Uiso calc R 1.000 H
H11 0.50480 0.19090 0.44150 0.0200 Uiso calc R 1.000 H
H12 0.75560 0.19090 0.54540 0.0170 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'
Cl Cl 0.1484 0.1585 '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
C3 O1 C4 . . . 106.04(14) yes
C1 N1 C2 . . . 107.65(14) yes
C1 N1 C7 . . . 124.81(14) yes
C2 N1 C7 . . . 127.24(13) yes
N3 N2 C1 . . . 113.82(14) yes
N2 N3 C2 . . . 103.93(13) yes
N3 N2 H2 . . . 123.10 no
C1 N2 H2 . . . 123.09 no
N1 C1 N2 . . . 103.43(13) yes
S1 C1 N1 . . . 127.51(14) yes
S1 C1 N2 . . . 129.05(13) yes
N1 C2 N3 . . . 111.16(13) yes
N1 C2 C3 . . . 125.81(15) yes
N3 C2 C3 . . . 123.03(15) yes
O1 C3 C2 . . . 113.89(14) yes
C2 C3 C6 . . . 135.68(16) no
O1 C3 C6 . . . 110.38(14) yes
O1 C4 C5 . . . 110.71(14) yes
C4 C5 C6 . . . 106.48(15) no
C3 C6 C5 . . . 106.40(15) no
C8 C7 C12 . . . 121.83(16) no
N1 C7 C8 . . . 118.51(14) yes
N1 C7 C12 . . . 119.65(15) yes
C7 C8 C9 . . . 119.23(15) no
C8 C9 C10 . . . 118.82(16) no
Cl1 C10 C11 . . . 119.36(13) yes
Cl1 C10 C9 . . . 118.34(14) yes
C9 C10 C11 . . . 122.30(17) no
C10 C11 C12 . . . 118.69(15) no
C7 C12 C11 . . . 119.11(16) no
O1 C4 H4 . . . 124.64 no
C5 C4 H4 . . . 124.65 no
C4 C5 H5 . . . 126.72 no
C6 C5 H5 . . . 126.80 no
C3 C6 H6 . . . 126.82 no
C5 C6 H6 . . . 126.79 no
C7 C8 H8 . . . 120.37 no
C9 C8 H8 . . . 120.39 no
C8 C9 H9 . . . 120.58 no
C10 C9 H9 . . . 120.60 no
C10 C11 H11 . . . 120.64 no
C12 C11 H11 . . . 120.67 no
C7 C12 H12 . . . 120.45 no
C11 C12 H12 . . . 120.44 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
Cl1 C10 . . 1.747(2) yes
S1 C1 . . 1.6773(19) yes
O1 C3 . . 1.376(2) yes
O1 C4 . . 1.372(2) yes
N1 C1 . . 1.383(2) yes
N1 C2 . . 1.384(2) yes
N1 C7 . . 1.446(2) yes
N2 N3 . . 1.374(2) yes
N2 C1 . . 1.346(2) yes
N3 C2 . . 1.311(2) yes
N2 H2 . . 0.86 no
C2 C3 . . 1.448(2) no
C3 C6 . . 1.360(3) no
C4 C5 . . 1.355(3) no
C5 C6 . . 1.427(2) no
C7 C12 . . 1.388(2) no
C7 C8 . . 1.386(3) no
C8 C9 . . 1.391(3) no
C9 C10 . . 1.388(2) no
C10 C11 . . 1.385(3) no
C11 C12 . . 1.397(3) no
C4 H4 . . 0.93 no
C5 H5 . . 0.93 no
C6 H6 . . 0.93 no
C8 H8 . . 0.93 no
C9 H9 . . 0.93 no
C11 H11 . . 0.93 no
C12 H12 . . 0.93 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
Cl1 C6 3.406(3) . 2_666 no
Cl1 H5 2.9929 . 1_445 no
Cl1 H6 2.7679 . 2_666 no
S1 N2 3.304(2) . 2_757 no
S1 C4 3.632(3) . 2_767 no
S1 H2 2.4808 . 2_757 no
O1 N3 2.726(2) . . no
O1 H8 2.7130 . 2_767 no
N1 N3 2.224(3) . . no
N2 N1 2.142(2) . . no
N2 S1 3.304(2) . 2_757 no
N2 C6 3.397(3) . 2_767 no
N3 C3 3.449(3) . 2_767 no
N3 O1 2.726(2) . . no
N3 N1 2.224(3) . . no
N3 C9 3.302(3) . 1_655 no
N3 C8 3.368(3) . 2_767 no
N2 H9 2.9291 . 1_655 no
N3 H9 2.4232 . 1_655 no
N3 H8 2.5575 . 2_767 no
C1 C4 3.540(3) . 2_767 no
C2 C2 3.459(3) . 2_767 no
C2 C3 3.589(3) . 2_767 no
C3 C8 3.572(3) . . no
C3 N3 3.449(3) . 2_767 no
C3 C2 3.589(3) . 2_767 no
C4 S1 3.632(3) . 2_767 no
C4 C10 3.598(3) . 1_665 no
C4 C1 3.540(3) . 2_767 no
C6 N2 3.397(3) . 2_767 no
C6 C8 3.390(3) . . no
C6 Cl1 3.406(3) . 2_666 no
C6 C7 3.218(3) . . no
C7 C6 3.218(3) . . no
C8 N3 3.368(3) . 2_767 no
C8 C6 3.390(3) . . no
C8 C3 3.572(3) . . no
C9 N3 3.302(3) . 1_455 no
C10 C4 3.598(3) . 1_445 no
C1 H2 3.0503 . 2_757 no
C4 H11 3.0498 . 2_766 no
C5 H12 2.8615 . 2_766 no
C7 H6 2.7705 . . no
C7 H4 3.0623 . 1_445 no
C8 H6 2.7985 . . no
C8 H4 2.9165 . 1_445 no
C9 H4 2.9109 . 1_445 no
C10 H4 3.0195 . 1_445 no
H2 S1 2.4808 . 2_757 no
H2 C1 3.0503 . 2_757 no
H2 H2 2.4764 . 2_757 no
H4 C7 3.0623 . 1_665 no
H4 C8 2.9165 . 1_665 no
H4 C9 2.9109 . 1_665 no
H4 C10 3.0195 . 1_665 no
H5 Cl1 2.9929 . 1_665 no
H6 C7 2.7705 . . no
H6 C8 2.7985 . . no
H6 Cl1 2.7679 . 2_666 no
H8 O1 2.7130 . 2_767 no
H8 N3 2.5575 . 2_767 no
H9 N2 2.9291 . 1_455 no
H9 N3 2.4232 . 1_455 no
H11 C4 3.0498 . 2_766 no
H12 C5 2.8615 . 2_766 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
N2 H2 S1 2_757 0.86 2.48 3.304(2) 160 yes
C6 H6 Cl1 2_666 0.93 2.77 3.406(3) 127 yes
C8 H8 N3 2_767 0.93 2.56 3.368(3) 146 yes
C9 H9 N3 1_455 0.93 2.42 3.302(3) 158 yes
C4 H4 Cg1 1_665 0.93 2.71 3.529(3) 147 yes
C6 H6 Cg1 1_555 0.93 2.99 3.729(3) 138 yes
C12 H12 Cg2 2_766 0.93 3.09 3.733(3) 128 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
C4 O1 C3 C6 . . . . -0.14(18) no
C4 O1 C3 C2 . . . . -178.01(13) no
C3 O1 C4 C5 . . . . -0.02(19) no
C2 N1 C1 S1 . . . . 178.54(13) no
C7 N1 C1 N2 . . . . -175.07(14) no
C1 N1 C2 N3 . . . . 0.38(18) no
C7 N1 C2 C3 . . . . -6.3(3) no
C7 N1 C2 N3 . . . . 174.20(14) no
C1 N1 C2 C3 . . . . 179.92(17) no
C2 N1 C7 C12 . . . . 104.28(18) no
C1 N1 C7 C12 . . . . -82.9(2) no
C2 N1 C1 N2 . . . . -1.06(17) no
C2 N1 C7 C8 . . . . -74.7(2) no
C7 N1 C1 S1 . . . . 4.5(2) no
C1 N1 C7 C8 . . . . 98.11(18) no
C1 N2 N3 C2 . . . . -1.23(18) no
N3 N2 C1 N1 . . . . 1.44(18) no
N3 N2 C1 S1 . . . . -178.16(13) no
N2 N3 C2 N1 . . . . 0.47(17) no
N2 N3 C2 C3 . . . . -179.09(14) no
N3 C2 C3 O1 . . . . 4.5(2) no
N1 C2 C3 C6 . . . . 7.9(3) no
N1 C2 C3 O1 . . . . -175.00(14) no
N3 C2 C3 C6 . . . . -172.65(18) no
C2 C3 C6 C5 . . . . 177.44(17) no
O1 C3 C6 C5 . . . . 0.23(18) no
O1 C4 C5 C6 . . . . 0.14(19) no
C4 C5 C6 C3 . . . . -0.22(19) no
C12 C7 C8 C9 . . . . -1.1(2) no
N1 C7 C12 C11 . . . . -179.12(14) no
C8 C7 C12 C11 . . . . -0.2(2) no
N1 C7 C8 C9 . . . . 177.88(14) no
C7 C8 C9 C10 . . . . 1.6(2) no
C8 C9 C10 C11 . . . . -0.9(2) no
C8 C9 C10 Cl1 . . . . 178.33(12) no
Cl1 C10 C11 C12 . . . . -179.57(12) no
C9 C10 C11 C12 . . . . -0.4(2) no
C10 C11 C12 C7 . . . . 0.9(2) no