#------------------------------------------------------------------------------
#$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2006201.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_2006201
loop_
_publ_author_name
'Bruno, G.'
'Grasso, S.'
'Monforte, P.'
'Nicol\'o, F.'
'Scopelliti, R.'
_publ_section_title
;
 1-(2-Fluorophenyl)-and
 1-(3-Fluorophenyl)-1<i>H</i>,3<i>H</i>-thiazolo[3,4-<i>a</i>]benzimidazole
;
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              764
_journal_page_last               767
_journal_volume                  53
_journal_year                    1997
_chemical_formula_moiety         'C15 H11 F N2 S'
_chemical_formula_sum            'C15 H11 F N2 S'
_chemical_formula_weight         270.32
_chemical_name_systematic
;
1-(3-Fluorophenyl)-1H,3H-thiazolo[3,4-a]benzimidazole
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_cell_angle_alpha                90.00
_cell_angle_beta                 107.560(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.2490(10)
_cell_length_b                   7.4210(10)
_cell_length_c                   15.867(2)
_cell_measurement_reflns_used    46
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      17.06
_cell_measurement_theta_min      6.82
_cell_volume                     1262.8(3)
_computing_cell_refinement       'P3/V Control Software'
_computing_data_collection       'P3/V Control Software (Siemens, 1989)'
_computing_data_reduction        'SHELXTL-Plus (Sheldrick, 1991)'
_computing_molecular_graphics    SHELXTL-Plus
_computing_publication_material  'PARST95 (Nardelli, 1995), SHELXL-93'
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       'Siemens R3m/V diffractometer'
_diffrn_measurement_method       \w-2\q
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0109
_diffrn_reflns_av_sigmaI/netI    0.0186
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -1
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -1
_diffrn_reflns_number            2908
_diffrn_reflns_theta_max         25.04
_diffrn_reflns_theta_min         1.90
_diffrn_standards_decay_%        1
_diffrn_standards_interval_count 197
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.254
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.422
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    none
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.346
_refine_diff_density_min         -0.206
_refine_ls_extinction_coef       0.0006(13)
_refine_ls_extinction_method     'SHELXL93 (Sheldrick, 1993)'
_refine_ls_goodness_of_fit_all   1.049
_refine_ls_goodness_of_fit_obs   1.171
_refine_ls_hydrogen_treatment    'H atoms freely refined with U~iso~'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2232
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_restrained_S_obs      1.171
_refine_ls_R_factor_all          0.0455
_refine_ls_R_factor_obs          0.0347
_refine_ls_shift/esd_max         -0.001
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme
'calc w = 1/[\s^2^(Fo^2^)+(0.0650P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_wR_factor_all         0.1011
_refine_ls_wR_factor_obs         0.0977
_reflns_number_observed          1722
_reflns_number_total             2232
_reflns_observed_criterion       >2\s(I)
_[local]_cod_data_source_file    cf1149.cif
_[local]_cod_data_source_block   2
_cod_database_code               2006201
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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 0.0550(3) 0.0737(4) 0.0549(3) 0.0053(3) 0.0163(2) -0.0075(3)
C1 0.0502(10) 0.0389(10) 0.0592(12) 0.0039(8) 0.0222(9) 0.0036(9)
N2 0.0437(8) 0.0559(10) 0.0486(8) 0.0083(7) 0.0216(7) 0.0044(7)
C8 0.0539(11) 0.0494(11) 0.0497(10) 0.0152(9) 0.0245(9) 0.0063(9)
C9 0.0647(12) 0.0648(14) 0.0504(11) 0.0175(11) 0.0253(10) 0.0032(11)
C2 0.0480(10) 0.0473(11) 0.0492(10) 0.0110(8) 0.0201(8) 0.0038(9)
C7 0.0482(10) 0.0473(11) 0.0584(11) 0.0086(8) 0.0222(9) 0.0082(9)
N1 0.0524(9) 0.0628(11) 0.0584(10) 0.0109(8) 0.0286(8) 0.0126(8)
C3 0.0588(12) 0.0718(15) 0.0543(12) 0.0131(11) 0.0248(10) 0.0043(11)
C4 0.0734(15) 0.072(2) 0.0531(13) 0.0150(12) 0.0126(11) -0.0038(12)
C5 0.0609(13) 0.0665(14) 0.0687(14) -0.0001(11) 0.0092(12) 0.0020(11)
C6 0.0523(12) 0.0603(13) 0.079(2) -0.0001(10) 0.0217(11) 0.0127(11)
C10 0.0384(9) 0.0417(10) 0.0451(9) 0.0044(7) 0.0136(7) 0.0034(8)
C11 0.0489(10) 0.0426(11) 0.0570(11) 0.0011(9) 0.0206(9) 0.0051(9)
C12 0.0504(10) 0.0401(11) 0.0537(10) 0.0078(8) 0.0063(8) -0.0049(9)
F 0.0939(10) 0.0475(8) 0.0976(10) 0.0120(6) 0.0229(8) -0.0130(7)
C13 0.0482(10) 0.072(2) 0.0574(12) 0.0113(10) 0.0193(9) -0.0072(11)
C14 0.0532(11) 0.076(2) 0.0670(13) -0.0023(11) 0.0326(10) 0.0062(11)
C15 0.0528(11) 0.0451(12) 0.0620(12) -0.0012(9) 0.0230(9) 0.0059(9)
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_occupancy
_atom_site_type_symbol
S 0.18680(5) 0.16815(8) 0.38107(3) 0.0612(2) Uani d 1 S
C1 0.2597(2) 0.1348(3) 0.50089(13) 0.0482(4) Uani d 1 C
H1 0.2636(16) 0.008(3) 0.5143(11) 0.050(5) Uiso d 1 H
N2 0.38563(13) 0.2012(2) 0.51430(10) 0.0477(4) Uani d 1 N
C8 0.4290(2) 0.2227(3) 0.44368(12) 0.0491(5) Uani d 1 C
C9 0.3341(2) 0.1898(3) 0.35653(14) 0.0582(5) Uani d 1 C
H9A 0.3527(17) 0.078(3) 0.3292(13) 0.069(6) Uiso d 1 H
H9B 0.3246(19) 0.292(3) 0.3181(15) 0.065(6) Uiso d 1 H
C2 0.4845(2) 0.2321(2) 0.58946(12) 0.0469(4) Uani d 1 C
C7 0.5843(2) 0.2725(3) 0.55698(13) 0.0499(5) Uani d 1 C
N1 0.54717(14) 0.2649(2) 0.46475(11) 0.0552(4) Uani d 1 N
C3 0.4965(2) 0.2292(3) 0.67920(14) 0.0599(6) Uani d 1 C
H3 0.427(2) 0.197(3) 0.7009(14) 0.063(6) Uiso d 1 H
C4 0.6121(2) 0.2707(3) 0.7366(2) 0.0676(6) Uani d 1 C
H4 0.625(2) 0.267(3) 0.7989(17) 0.080(7) Uiso d 1 H
C5 0.7128(2) 0.3126(3) 0.7054(2) 0.0676(6) Uani d 1 C
H5 0.799(2) 0.340(3) 0.7466(15) 0.074(7) Uiso d 1 H
C6 0.7007(2) 0.3137(3) 0.6162(2) 0.0634(6) Uani d 1 C
H6 0.773(2) 0.344(3) 0.5991(14) 0.061(6) Uiso d 1 H
C10 0.18906(15) 0.2346(2) 0.55306(11) 0.0415(4) Uani d 1 C
C11 0.1945(2) 0.4209(3) 0.55921(12) 0.0485(5) Uani d 1 C
H11 0.2464(18) 0.486(3) 0.5357(13) 0.069(6) Uiso d 1 H
C12 0.1224(2) 0.5063(3) 0.60242(12) 0.0501(5) Uani d 1 C
F 0.12369(13) 0.6896(2) 0.60389(9) 0.0810(4) Uani d 1 F
C13 0.0480(2) 0.4180(3) 0.64257(13) 0.0585(5) Uani d 1 C
H13 -0.0003(18) 0.478(3) 0.6736(13) 0.071(6) Uiso d 1 H
C14 0.0441(2) 0.2336(3) 0.63808(14) 0.0622(6) Uani d 1 C
H14 -0.0113(18) 0.166(3) 0.6700(13) 0.060(6) Uiso d 1 H
C15 0.1141(2) 0.1413(3) 0.59308(14) 0.0520(5) Uani d 1 C
H15 0.1070(16) 0.017(3) 0.5875(12) 0.056(6) Uiso d 1 H
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'
F F 0.0171 0.0103 '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_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
3 0 6
5 2 -3
-5 -2 3
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
C9 S C1 94.69(9) y
N2 C1 C10 114.0(2) n
N2 C1 S 102.48(12) y
C10 C1 S 110.89(13) n
C8 N2 C2 107.24(14) y
C8 N2 C1 119.7(2) y
C2 N2 C1 132.63(15) n
N1 C8 N2 114.0(2) y
N1 C8 C9 131.7(2) n
N2 C8 C9 114.3(2) y
C8 C9 S 105.04(13) y
N2 C2 C3 133.3(2) n
N2 C2 C7 104.1(2) y
C3 C2 C7 122.6(2) ?
C6 C7 N1 129.6(2) n
C6 C7 C2 119.5(2) ?
N1 C7 C2 110.9(2) y
C8 N1 C7 103.72(15) y
C4 C3 C2 117.1(2) ?
C3 C4 C5 121.2(2) ?
C6 C5 C4 121.6(2) ?
C5 C6 C7 118.1(2) ?
C15 C10 C11 119.1(2) ?
C15 C10 C1 120.2(2) ?
C11 C10 C1 120.7(2) ?
C12 C11 C10 118.5(2) ?
F C12 C13 118.5(2) ?
F C12 C11 117.9(2) ?
C13 C12 C11 123.6(2) ?
C12 C13 C14 118.1(2) ?
C13 C14 C15 120.2(2) ?
C10 C15 C14 120.4(2) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S C9 1.820(2) y
S C1 1.846(2) y
C1 N2 1.453(2) y
C1 C10 1.504(2) n
N2 C8 1.359(2) y
N2 C2 1.382(2) y
C8 N1 1.308(2) y
C8 C9 1.490(3) y
C2 C3 1.389(3) ?
C2 C7 1.402(3) y
C7 C6 1.396(3) ?
C7 N1 1.396(3) y
C3 C4 1.378(3) ?
C4 C5 1.402(3) ?
C5 C6 1.380(3) ?
C10 C15 1.384(3) ?
C10 C11 1.386(3) ?
C11 C12 1.366(3) ?
C12 F 1.360(2) n
C12 C13 1.364(3) ?
C13 C14 1.370(3) ?
C14 C15 1.392(3) ?
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
C9 S C1 N2 17.84(14)
C9 S C1 C10 139.83(15)
C10 C1 N2 C8 -136.4(2)
S C1 N2 C8 -16.6(2)
C10 C1 N2 C2 52.4(3)
S C1 N2 C2 172.3(2)
C2 N2 C8 N1 0.0(2)
C1 N2 C8 N1 -173.2(2)
C2 N2 C8 C9 178.7(2)
C1 N2 C8 C9 5.4(2)
N1 C8 C9 S -172.6(2)
N2 C8 C9 S 9.1(2)
C1 S C9 C8 -15.7(2)
C8 N2 C2 C3 -179.9(2)
C1 N2 C2 C3 -7.9(3)
C8 N2 C2 C7 0.3(2)
C1 N2 C2 C7 172.2(2)
N2 C2 C7 C6 179.2(2)
C3 C2 C7 C6 -0.7(3)
N2 C2 C7 N1 -0.4(2)
C3 C2 C7 N1 179.7(2)
N2 C8 N1 C7 -0.3(2)
C9 C8 N1 C7 -178.6(2)
C6 C7 N1 C8 -179.1(2)
C2 C7 N1 C8 0.4(2)
N2 C2 C3 C4 -179.0(2)
C7 C2 C3 C4 0.8(3)
C2 C3 C4 C5 -0.4(3)
C3 C4 C5 C6 -0.1(4)
C4 C5 C6 C7 0.2(4)
N1 C7 C6 C5 179.7(2)
C2 C7 C6 C5 0.2(3)
N2 C1 C10 C15 -139.4(2)
S C1 C10 C15 105.6(2)
N2 C1 C10 C11 42.9(2)
S C1 C10 C11 -72.1(2)
C15 C10 C11 C12 -2.0(3)
C1 C10 C11 C12 175.8(2)
C10 C11 C12 F -176.6(2)
C10 C11 C12 C13 2.2(3)
F C12 C13 C14 177.8(2)
C11 C12 C13 C14 -1.0(3)
C12 C13 C14 C15 -0.4(3)
C11 C10 C15 C14 0.7(3)
C1 C10 C15 C14 -177.1(2)
C13 C14 C15 C10 0.5(3)