data_2010637
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2000
_journal_volume  56
_journal_page_first  222
_journal_page_last  224
_publ_section_title
;
3-(2-Furyl)-6-(4-methylphenyl)-7H-1,2,4-triazolo[3,4-b][1,3,4]thiadiazine
and its 6-phenyl analogue
;
loop_
_publ_author_name
  '\"Ozbey, S\"uheyla'
  'Ulusoy, Nuray'
  'Kendi, Engin'
_chemical_formula_moiety  'C14 H10 N4 O1 S1'
_chemical_formula_sum  'C14 H10 N4 O1 S1'
_chemical_formula_weight  282.33
_symmetry_cell_setting  monoclinic
_symmetry_space_group_name_H-M  'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
loop_
_symmetry_equiv_pos_as_xyz
  'x,y,z'
  '-x,-y,-z'
  '-x,y+1/2,-z+1/2'
  'x,-y+1/2,z+1/2'
_cell_length_a  8.799(2)
_cell_length_b  9.3020(10)
_cell_length_c  15.54370(10)
_cell_angle_alpha  90
_cell_angle_beta  97.400(10)
_cell_angle_gamma  90
_cell_volume  1261.6(2)
_cell_formula_units_Z  4
_cell_measurement_temperature  295
_exptl_crystal_density_diffrn  1.49
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
  S1  .89590(7)  .18735(7)  .20244(3)  .0524(2) Ueq . . S
  O1 1.3414(2)  .4792(2)  -.02180(10)
  .0570(5) Ueq . . O
  N1 1.2241(2)  .4280(2)  .13760(10)
  .0471(5) Ueq . . N
  N2 1.1453(2)  .3673(2)  .20160(10)
  .0503(6) Ueq . . N
  N3 1.0381(2)  .2935(2)  .07350(10)
  .0360(4) Ueq . . N
  N4  .9291(2)  .2432(2)  .00780(10)
  .0361(4) Ueq . . N
  C1  .8490(2)  .1343(2)  .02810(10)
  .0348(5) Ueq . . C
  C2  .8796(2)  .0584(2)  .11410(10)
  .0427(6) Ueq . . C
  C3 1.0355(2)  .2886(2)  .16140(10)
  .0424(6) Ueq . . C
  C4 1.1572(2)  .3840(2)  .06190(10)
  .0375(5) Ueq . . C
  C5 1.2036(2)  .4119(2)  -.02200(10)
  .0379(5) Ueq . . C
  C6 1.1443(2)  .3822(3)  -.10370(10)
  .0504(6) Ueq . . C
  C7 1.2492(3)  .4328(3)  -.1585(2)  .0525(6) Ueq . . C
  C8 1.3652(3)  .4893(3)  -.1067(2)  .0582(6) Ueq . . C
  C9  .7270(2)  .0858(2)  -.03990(10)
  .0351(5) Ueq . . C
  C10  .6663(2)  .1799(2)  -.10560(10)
  .0464(6) Ueq . . C
  C11  .5557(3)  .1338(3)  -.17050(10)
  .0527(6) Ueq . . C
  C12  .5046(2)  -.0071(3)  -.17250(10)
  .0490(6) Ueq . . C
  C13  .5629(3)  -.0999(2)  -.1079(2)  .0515(6) Ueq . . C
  C14  .6721(2)  -.0544(2)  -.04140(10)
  .0436(6) Ueq . . C
  H6 1.049  .336  -.121  .0646 Uiso . . H
  H7 1.238  .428  -.220  .0671 Uiso . . H
  H8 1.453  .531  -.126  .0747 Uiso . . H
  H10  .703  .276  -.106  .0595 Uiso . . H
  H11  .513  .199  -.214  .0684 Uiso . . H
  H12  .430  -.039  -.218  .0646 Uiso . . H
  H13  .528  -.197  -.109  .0659 Uiso . . H
  H14  .710  -.119  .004  .0570 Uiso . . H
  H21  .977  .005  .118  .0507 Uiso . . H
  H22  .797  -.004  .125  .0709 Uiso . . 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
_atom_site_aniso_type_symbol
  S1  .0625(3)  .0603(3)  .0352(2)  -.0072(3)  .0092(2)  -.0008(3) S
  O1  .0462(7)  .0660(10)
  .0580(8)  -.0227(7)  .0033(7)  -.0066(8) O
  N1  .0495(9)  .0424(9)  .0463(9)  -.0038(8)  -.0062(8)  -.0037(8) N
  N2  .0600(10)
  .0480(10)
  .0398(9)  -.0036(9)  -.0049(8)  -.0061(8) N
  N3  .0363(7)  .0355(8)  .0346(7)  -.0019(7)  -.0017(6)  -.0012(7) N
  N4  .0362(7)  .0371(8)  .0337(7)  -.0034(7)  -.0010(6)  -.0012(7) N
  C1  .0350(8)  .0339(9)  .0358(8)  .0023(8)  .0056(7)  -.0005(8) C
  C2  .0470(10)
  .0400(10)
  .0404(9)  -.0023(9)  .0030(8)  .0050(9) C
  C3  .0490(10)
  .0410(10)
  .0358(9)  .0030(9)  -.0001(8)  -.0016(9) C
  C4  .0353(9)  .0290(9)  .0460(10)
  .0011(8)  -.0033(8)  -.0027(8) C
  C5  .0349(9)  .0284(9)  .0490(10)
  -.0024(8)  .0005(8)  .0002(8) C
  C6  .0450(10)
  .0580(10)
  .0460(10)
  -.0160(10)
  -.0022(9)  .0030(10)
  C
  C7  .0510(10)
  .0590(10)
  .0470(10)
  -.0110(10)
  .0048(9)  .0050(10)
  C
  C8  .0540(10)
  .0630(10)
  .0590(10)
  -.0160(10)
  .0130(10)
  .0020(10)
  C
  C9  .0345(8)  .0341(9)  .0373(8)  -.0018(8)  .0072(7)  -.0031(8) C
  C10  .0520(10)
  .0400(10)
  .0450(10)
  -.0090(10)
  -.0027(9)  .0041(9) C
  C11  .0580(10)
  .0510(10)
  .0460(10)
  -.0050(10)
  -.0050(10)
  .0030(10)
  C
  C12  .0410(10)
  .0580(10)
  .0470(10)
  -.0060(10)
  .0020(9)  -.0140(10)
  C
  C13  .0510(10)
  .0370(10)
  .0660(10)
  -.0090(10)
  .0060(10)
  -.0110(10)
  C
  C14  .0470(10)
  .0320(10)
  .0520(10)
  .0003(9)  .0066(9)  -.0002(9) C
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 C2 . . 1.815(2) yes
  S1 C3 . . 1.733(2) yes
  O1 C5 . . 1.364(2) yes
  O1 C8 . . 1.365(3) yes
  N1 N2 . . 1.403(3) yes
  N1 C4 . . 1.311(2) yes
  N2 C3 . . 1.306(3) yes
  N3 N4 . . 1.389(2) yes
  N3 C3 . . 1.369(2) yes
  N3 C4 . . 1.374(2) yes
  N4 C1 . . 1.296(3) yes
  C1 C2 . . 1.506(3) yes
  C1 C9 . . 1.477(2) yes
  C2 H21 . .  .989 no
  C2 H22 . .  .960 no
  C4 C5 . . 1.439(3) yes
  C5 C6 . . 1.338(3) yes
  C6 C7 . . 1.415(3) yes
  C6 H6 . .  .950 no
  C7 C8 . . 1.325(3) yes
  C7 H7 . .  .950 no
  C8 H8 . .  .950 no
  C9 C10 . . 1.397(3) yes
  C9 C14 . . 1.390(3) yes
  C10 C11 . . 1.377(3) yes
  C10 H10 . .  .950 no
  C11 C12 . . 1.385(3) yes
  C11 H11 . .  .950 no
  C12 C13 . . 1.372(3) yes
  C12 H12 . .  .950 no
  C13 C14 . . 1.384(3) yes
  C13 H13 . .  .950 no
  C14 H14 . .  .950 no