#------------------------------------------------------------------------------
#$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2006200.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_2006200
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-(2-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                 108.390(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.3440(10)
_cell_length_b                   7.4370(10)
_cell_length_c                   15.542(2)
_cell_measurement_reflns_used    36
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      14.45
_cell_measurement_theta_min      6.57
_cell_volume                     1244.2(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  0.0170
_diffrn_reflns_av_sigmaI/netI    0.0234
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            5826
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_min         1.89
_diffrn_standards_decay_%        0.82
_diffrn_standards_interval_count 197
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.258
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.443
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    none
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.161
_refine_diff_density_min         -0.157
_refine_ls_extinction_coef       0.0004(10)
_refine_ls_extinction_method     'SHELXL93 (Sheldrick, 1993)'
_refine_ls_goodness_of_fit_all   0.933
_refine_ls_goodness_of_fit_obs   1.051
_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         2210
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.933
_refine_ls_restrained_S_obs      1.051
_refine_ls_R_factor_all          0.0414
_refine_ls_R_factor_obs          0.0288
_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^)+(0.0478P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_wR_factor_all         0.0750
_refine_ls_wR_factor_obs         0.0721
_reflns_number_observed          1667
_reflns_number_total             2210
_reflns_observed_criterion       >2\s(I)
_[local]_cod_data_source_file    cf1149.cif
_[local]_cod_data_source_block   1
_cod_database_code               2006200
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 0.0462(3) 0.0676(3) 0.0467(3) -0.0037(2) 0.0167(2) -0.0069(2)
C1 0.0435(9) 0.0394(9) 0.0478(9) 0.0008(7) 0.0206(7) 0.0034(7)
N2 0.0388(7) 0.0525(8) 0.0424(7) 0.0032(6) 0.0199(6) 0.0028(6)
C8 0.0464(10) 0.0431(9) 0.0432(9) 0.0084(7) 0.0219(7) 0.0047(7)
C9 0.0518(10) 0.0559(11) 0.0432(9) 0.0063(9) 0.0224(8) 0.0007(9)
C2 0.0414(8) 0.0437(9) 0.0434(9) 0.0071(7) 0.0176(7) 0.0024(7)
C7 0.0424(9) 0.0417(9) 0.0482(9) 0.0073(7) 0.0194(7) 0.0064(7)
N1 0.0438(8) 0.0541(8) 0.0496(8) 0.0046(6) 0.0241(6) 0.0066(6)
C3 0.0518(11) 0.0685(12) 0.0491(10) 0.0102(9) 0.0240(9) 0.0021(9)
C4 0.0624(12) 0.0694(13) 0.0438(11) 0.0103(10) 0.0098(9) -0.0042(9)
C5 0.0513(11) 0.0603(12) 0.0594(12) 0.0004(9) 0.0079(10) -0.0001(9)
C6 0.0451(10) 0.0563(11) 0.0642(12) 0.0001(9) 0.0195(9) 0.0097(9)
C10 0.0351(8) 0.0392(8) 0.0375(8) 0.0016(6) 0.0137(6) 0.0032(6)
C11 0.0517(10) 0.0418(10) 0.0575(11) -0.0036(8) 0.0243(8) 0.0027(8)
C12 0.0570(11) 0.0447(11) 0.0601(11) 0.0039(9) 0.0168(9) -0.0099(8)
C13 0.0430(10) 0.0673(13) 0.0512(10) 0.0068(9) 0.0178(8) -0.0093(9)
C14 0.0390(9) 0.0634(12) 0.0534(11) -0.0032(8) 0.0218(8) 0.0028(9)
C15 0.0373(8) 0.0384(9) 0.0407(8) -0.0013(7) 0.0095(7) 0.0037(7)
F 0.0619(6) 0.0412(5) 0.0761(7) -0.0070(5) 0.0286(5) 0.0056(5)
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 0.18702(4) 0.16143(7) 0.88279(3) 0.0530(2) Uani d 1 S
C1 0.26677(15) 0.1370(2) 1.00589(11) 0.0421(4) Uani d 1 C
H1 0.2740(14) 0.011(2) 1.0239(10) 0.044(4) Uiso d 1 H
N2 0.38922(12) 0.2087(2) 1.01575(9) 0.0429(3) Uani d 1 N
C8 0.4282(2) 0.2206(2) 0.94137(10) 0.0424(4) Uani d 1 C
C9 0.3301(2) 0.1789(3) 0.85411(12) 0.0486(4) Uani d 1 C
H9A 0.3477(16) 0.068(3) 0.8309(12) 0.065(6) Uiso d 1 H
H9B 0.3238(16) 0.279(3) 0.8133(13) 0.058(5) Uiso d 1 H
C2 0.49157(15) 0.2442(2) 1.09088(11) 0.0419(4) Uani d 1 C
C7 0.58748(15) 0.2798(2) 1.05429(11) 0.0429(4) Uani d 1 C
N1 0.54515(13) 0.2628(2) 0.95962(9) 0.0469(4) Uani d 1 N
C3 0.5086(2) 0.2514(3) 1.18328(12) 0.0546(5) Uani d 1 C
H3 0.4408(18) 0.221(3) 1.2035(13) 0.061(5) Uiso d 1 H
C4 0.6257(2) 0.2968(3) 1.23876(13) 0.0602(5) Uani d 1 C
H4 0.6391(17) 0.302(2) 1.3007(13) 0.063(6) Uiso d 1 H
C5 0.7221(2) 0.3333(3) 1.20367(14) 0.0592(5) Uani d 1 C
H5 0.8033(16) 0.365(2) 1.2454(12) 0.058(5) Uiso d 1 H
C6 0.7048(2) 0.3249(3) 1.11212(13) 0.0546(5) Uani d 1 C
H6 0.7689(18) 0.350(2) 1.0882(13) 0.066(6) Uiso d 1 H
C10 0.19690(14) 0.2368(2) 1.05871(10) 0.0367(4) Uani d 1 C
C11 0.2062(2) 0.4213(2) 1.07216(12) 0.0487(4) Uani d 1 C
H11 0.2600(16) 0.481(2) 1.0509(12) 0.063(6) Uiso d 1 H
C12 0.1338(2) 0.5098(3) 1.11504(13) 0.0543(5) Uani d 1 C
H12 0.1360(18) 0.641(3) 1.1196(13) 0.071(6) Uiso d 1 H
C13 0.0521(2) 0.4147(3) 1.14720(12) 0.0531(5) Uani d 1 C
H13 0.0017(17) 0.471(3) 1.1791(12) 0.066(6) Uiso d 1 H
C14 0.0429(2) 0.2317(3) 1.13713(12) 0.0502(4) Uani d 1 C
H14 -0.0104(19) 0.164(3) 1.1585(14) 0.071(6) Uiso d 1 H
C15 0.11506(14) 0.1474(2) 1.09288(10) 0.0395(4) Uani d 1 C
F 0.10416(9) -0.03414(13) 1.08143(7) 0.0581(3) Uani d 1 F
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
-1 -2 6
1 1 5
-1 -1 -5
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 94.44(8) yes
N2 C1 C10 114.41(13) no
N2 C1 S 102.30(11) yes
C10 C1 S 110.25(11) no
C8 N2 C2 106.97(14) yes
C8 N2 C1 119.33(14) yes
C2 N2 C1 132.70(14) no
N1 C8 N2 114.23(14) yes
N1 C8 C9 131.60(15) no
N2 C8 C9 114.15(15) yes
C8 C9 S 105.05(12) yes
N2 C2 C3 133.2(2) no
N2 C2 C7 104.17(14) yes
C3 C2 C7 122.6(2) ?
C6 C7 N1 129.8(2) no
C6 C7 C2 119.3(2) ?
N1 C7 C2 110.85(14) yes
C8 N1 C7 103.76(13) yes
C4 C3 C2 116.7(2) ?
C3 C4 C5 121.5(2) ?
C6 C5 C4 121.5(2) ?
C5 C6 C7 118.3(2) ?
C15 C10 C11 116.6(2) ?
C15 C10 C1 120.50(14) ?
C11 C10 C1 122.82(15) ?
C12 C11 C10 121.1(2) ?
C11 C12 C13 120.1(2) ?
C14 C13 C12 120.2(2) ?
C13 C14 C15 118.3(2) ?
F C15 C14 118.25(15) ?
F C15 C10 118.20(14) ?
C14 C15 C10 123.5(2) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S C9 1.818(2) yes
S C1 1.849(2) yes
C1 N2 1.450(2) yes
C1 C10 1.504(2) no
N2 C8 1.364(2) yes
N2 C2 1.388(2) yes
C8 N1 1.305(2) yes
C8 C9 1.490(2) yes
C2 C3 1.388(2) ?
C2 C7 1.403(2) yes
C7 C6 1.391(2) ?
C7 N1 1.402(2) yes
C3 C4 1.378(3) ?
C4 C5 1.394(3) ?
C5 C6 1.375(3) ?
C10 C15 1.377(2) ?
C10 C11 1.387(2) ?
C11 C12 1.377(3) ?
C12 C13 1.379(3) ?
C13 C14 1.370(3) ?
C14 C15 1.375(2) ?
C15 F 1.362(2) no
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 19.84(12)
C9 S C1 C10 141.93(13)
C10 C1 N2 C8 -138.56(14)
S C1 N2 C8 -19.4(2)
C10 C1 N2 C2 54.5(2)
S C1 N2 C2 173.74(14)
C2 N2 C8 N1 -0.9(2)
C1 N2 C8 N1 -170.92(14)
C2 N2 C8 C9 177.77(14)
C1 N2 C8 C9 7.8(2)
N1 C8 C9 S -173.0(2)
N2 C8 C9 S 8.6(2)
C1 S C9 C8 -16.67(13)
C8 N2 C2 C3 180.0(2)
C1 N2 C2 C3 -11.9(3)
C8 N2 C2 C7 1.2(2)
C1 N2 C2 C7 169.3(2)
N2 C2 C7 C6 178.71(15)
C3 C2 C7 C6 -0.3(3)
N2 C2 C7 N1 -1.1(2)
C3 C2 C7 N1 179.9(2)
N2 C8 N1 C7 0.2(2)
C9 C8 N1 C7 -178.2(2)
C6 C7 N1 C8 -179.2(2)
C2 C7 N1 C8 0.6(2)
N2 C2 C3 C4 -178.3(2)
C7 C2 C3 C4 0.4(3)
C2 C3 C4 C5 -0.1(3)
C3 C4 C5 C6 -0.3(3)
C4 C5 C6 C7 0.4(3)
N1 C7 C6 C5 179.7(2)
C2 C7 C6 C5 -0.1(3)
N2 C1 C10 C15 -148.17(14)
S C1 C10 C15 97.20(15)
N2 C1 C10 C11 34.8(2)
S C1 C10 C11 -79.8(2)
C15 C10 C11 C12 -2.0(2)
C1 C10 C11 C12 175.1(2)
C10 C11 C12 C13 1.3(3)
C11 C12 C13 C14 0.4(3)
C12 C13 C14 C15 -1.3(3)
C13 C14 C15 F -178.81(15)
C13 C14 C15 C10 0.5(2)
C11 C10 C15 F -179.58(14)
C1 C10 C15 F 3.2(2)
C11 C10 C15 C14 1.1(2)
C1 C10 C15 C14 -176.08(15)