data_2011922
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2001
_journal_volume  57
_journal_page_first  572
_journal_page_last  574
_publ_section_title
;
7-Chloro-1-(2,6-difluorophenyl)-1H,3H-thiazolo[3,4-a]benzimidazole and
1-(2,6-difluorophenyl)-6-methyl-1H,3H-thiazolo[3,4-a]benzimidazole
;
loop_
_publ_author_name
  "Nicol\'o, Francesco"
  'Bruno, Giuseppe'
  'Scopelliti, Rosario'
  'Grasso, Silvana'
  'Rao, Angela'
  "Zappal\'a, Maria"
_chemical_formula_moiety  'C15 H9 Cl F2 N2 S'
_chemical_formula_sum  'C15 H9 Cl F2 N2 S'
_chemical_formula_weight  322.75
_symmetry_cell_setting  Monoclinic
_symmetry_space_group_name_H-M  'P 21/n'
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'
_cell_length_a  10.292(2)
_cell_length_b  5.7410(10)
_cell_length_c  23.474(4)
_cell_angle_alpha  90.00
_cell_angle_beta  95.050(10)
_cell_angle_gamma  90.00
_cell_volume  1381.6(4)
_cell_formula_units_Z  4
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.552
_diffrn_ambient_temperature  293(2)
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_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
  S  .77120(4)  .20390(10)  .36066(2)  .05641(18) Uani d . (I) . . S
  C1  .59458(15)  .2581(3)  .35513(7)  .0367(4) Uani d . (I) . . C
  H1  .5788  .4087  .3729  .060 Uiso calc R (I) . . H
  N2  .54823(12)  .0747(2)  .39076(5)  .0340(3) Uani d . (I) . . N
  C8  .62711(16)  -.1072(3)  .40779(7)  .0381(4) Uani d . (I) . . C
  C9  .76023(17)  -.0928(4)  .38772(8)  .0503(5) Uani d . (I) . . C
  H9A  .7707  -.2056  .3577  .060 Uiso calc R (I) . . H
  H9B  .8265  -.1207  .4190  .060 Uiso calc R (I) . . H
  C2  .43027(14)  .0379(3)  .41299(6)  .0321(3) Uani d . (I) . . C
  C7  .44740(16)  -.1742(3)  .44275(6)  .0357(4) Uani d . (I) . . C
  N1  .57304(14)  -.2620(2)  .43858(6)  .0410(3) Uani d . (I) . . N
  C3  .31737(15)  .1695(3)  .41126(6)  .0367(4) Uani d . (I) . . C
  H3  .3078  .3097  .3915  .060 Uiso calc R (I) . . H
  C4  .21987(16)  .0767(3)  .44122(7)  .0408(4) Uani d . (I) . . C
  Cl  .07486(5)  .23378(11)  .44232(2)  .06610(19) Uani d . (I) . . Cl
  C5  .23216(17)  -.1342(3)  .47046(7)  .0448(4) Uani d . (I) . . C
  H5  .1625  -.1900  .4891  .060 Uiso calc R (I) . . H
  C6  .34588(18)  -.2614(3)  .47220(7)  .0430(4) Uani d . (I) . . C
  H6  .3547  -.4008  .4923  .060 Uiso calc R (I) . . H
  C10  .52532(16)  .2557(3)  .29540(7)  .0377(4) Uani d . (I) . . C
  C11  .53815(19)  .0806(4)  .25598(7)  .0493(5) Uani d . (I) . . C
  F1  .61742(13)  -.1004(2)  .27117(5)  .0717(4) Uani d . (I) . . F
  C12  .4723(2)  .0788(4)  .20216(8)  .0626(6) Uani d . (I) . . C
  H12  .4839  -.0423  .1768  .060 Uiso calc R (I) . . H
  C13  .3896(2)  .2595(4)  .18694(8)  .0656(6) Uani d . (I) . . C
  H13  .3449  .2613  .1507  .060 Uiso calc R (I) . . H
  C14  .3716(2)  .4380(4)  .22432(8)  .0620(6) Uani d . (I) . . C
  H14  .3149  .5600  .2140  .060 Uiso calc R (I) . . H
  C15  .43971(18)  .4317(3)  .27741(7)  .0469(4) Uani d . (I) . . C
  F2  .41965(13)  .6049(2)  .31481(5)  .0669(4) Uani d . (I) . . F
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
  S  .0339(2)  .0676(4)  .0677(3)  -.0055(2)  .0040(2)  .0146(3)
  C1  .0354(8)  .0391(9)  .0358(8)  -.0039(7)  .0036(6)  .0025(7)
  N2  .0356(7)  .0363(7)  .0301(6)  -.0008(6)  .0026(5)  .0032(5)
  C8  .0408(8)  .0402(9)  .0325(8)  .0035(7)  -.0013(6)  -.0021(7)
  C9  .0409(9)  .0574(12)  .0524(10)  .0085(9)  .0027(8)  .0041(9)
  C2  .0360(8)  .0373(8)  .0226(6)  -.0057(7)  .0003(6)  -.0005(6)
  C7  .0447(9)  .0361(8)  .0257(7)  -.0034(7)  -.0007(6)  -.0020(6)
  N1  .0488(8)  .0381(8)  .0354(7)  .0026(6)  -.0010(6)  .0015(6)
  C3  .0375(8)  .0432(9)  .0289(7)  -.0033(7)  -.0007(6)  .0016(7)
  C4  .0354(8)  .0547(11)  .0322(8)  -.0023(8)  .0022(6)  -.0021(8)
  Cl  .0400(3)  .0878(4)  .0725(4)  .0091(2)  .0157(2)  .0161(3)
  C5  .0471(10)  .0548(11)  .0332(8)  -.0138(9)  .0067(7)  .0010(8)
  C6  .0577(11)  .0413(9)  .0300(8)  -.0108(8)  .0033(7)  .0040(7)
  C10  .0395(8)  .0434(9)  .0310(8)  -.0035(7)  .0076(6)  .0051(7)
  C11  .0536(10)  .0577(12)  .0368(9)  .0067(9)  .0058(8)  .0011(8)
  F1  .0870(9)  .0710(8)  .0557(7)  .0301(7)  -.0024(6)  -.0134(6)
  C12  .0755(14)  .0783(15)  .0342(9)  .0015(12)  .0056(9)  -.0099(10)
  C13  .0741(14)  .0868(16)  .0337(9)  -.0020(13)  -.0075(9)  .0075(11)
  C14  .0692(13)  .0664(14)  .0477(10)  .0096(11)  -.0097(9)  .0130(10)
  C15  .0531(10)  .0477(11)  .0397(9)  -.0003(9)  .0025(8)  .0040(8)
  F2  .0817(8)  .0555(7)  .0607(7)  .0221(6)  -.0096(6)  -.0068(6)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
  S C9 . 1.825(2) yes
  S C1 . 1.8375(17) yes
  C1 N2 . 1.451(2) yes
  C1 C10 . 1.516(2) ?
  N2 C8 . 1.361(2) yes
  N2 C2 . 1.3792(19) yes
  C8 N1 . 1.301(2) yes
  C8 C9 . 1.490(2) yes
  C2 C3 . 1.384(2) ?
  C2 C7 . 1.407(2) ?
  C7 C6 . 1.396(2) ?
  C7 N1 . 1.399(2) yes
  C3 C4 . 1.382(2) ?
  C4 C5 . 1.392(3) ?
  C4 Cl . 1.7459(18) ?
  C5 C6 . 1.377(3) ?
  C10 C11 . 1.381(2) ?
  C10 C15 . 1.382(2) ?
  C11 F1 . 1.349(2) ?
  C11 C12 . 1.380(3) ?
  C12 C13 . 1.369(3) ?
  C13 C14 . 1.372(3) ?
  C14 C15 . 1.375(3) ?
  C15 F2 . 1.354(2) ?