#------------------------------------------------------------------------------
#$Date: 2017-01-27 16:32:39 +0200 (Fri, 27 Jan 2017) $
#$Revision: 191031 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/19/2011923.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_2011923
loop_
_publ_author_name
'Nicoló, Francesco'
'Bruno, Giuseppe'
'Scopelliti, Rosario'
'Grasso, Silvana'
'Rao, Angela'
'Zappalá, Maria'
_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
;
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              572
_journal_page_last               574
_journal_paper_doi               10.1107/S0108270101001421
_journal_volume                  57
_journal_year                    2001
_chemical_formula_moiety         'C16 H12 F2 N2 S'
_chemical_formula_sum            'C16 H12 F2 N2 S'
_chemical_formula_weight         302.34
_chemical_name_systematic
;
1-(2,6-Difluorophenyl)-6-methyl-1H,3H-thiazolo[3,4-a]benzimidazole
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_cell_angle_alpha                108.86(2)
_cell_angle_beta                 106.960(10)
_cell_angle_gamma                105.46(2)
_cell_formula_units_Z            2
_cell_length_a                   7.6160(10)
_cell_length_b                   10.202(3)
_cell_length_c                   10.868(2)
_cell_measurement_reflns_used    40
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      15.78
_cell_measurement_theta_min      7.23
_cell_volume                     701.0(3)
_computing_cell_refinement       P3/V
_computing_data_collection       'P3/V (Siemens, 1989)'
_computing_data_reduction        'SHELXTL-Plus (Sheldrick, 1990)'
_computing_molecular_graphics    'XPW (Siemens, 1996)'
_computing_publication_material
'locally modified PARST97 (Nardelli, 1995) and SHELXL97'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altomare, 1994)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full .000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Siemens P4'
_diffrn_measurement_method       ω-2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     .71073
_diffrn_reflns_av_R_equivalents  .0108
_diffrn_reflns_av_sigmaI/netI    .0315
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -4
_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            3013
_diffrn_reflns_theta_full        .50
_diffrn_reflns_theta_max         24.55
_diffrn_reflns_theta_min         2.18
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 197
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    .247
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.432
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       irregular
_exptl_crystal_F_000             312
_exptl_crystal_size_max          .30
_exptl_crystal_size_mid          .28
_exptl_crystal_size_min          .26
_refine_diff_density_max         .175
_refine_diff_density_min         -.154
_refine_ls_extinction_coef       .008(2)
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   .916
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2342
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      .916
_refine_ls_R_factor_all          .0459
_refine_ls_R_factor_gt           .0302
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         <0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0427P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .0729
_reflns_number_gt                1713
_reflns_number_total             2342
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            av1059.cif
_cod_data_source_block           2
_cod_depositor_comments
;
 Changing the _atom_site_occupancy data item value from '?' to '1'
 for all fully occupied atom sites.

 Antanas Vaitkus,
 2017-01-27

The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 

Luca 25/2/2014:
changed _atom_site_occupancy values from (I) to ?
;
_cod_database_code               2011923
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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_[sic]
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
_atom_site_occupancy
S .31356(8) .52479(6) .84683(5) .05986(18) Uani d . (I) . . S 1
C1 .5261(2) .58103(18) .79877(16) .0411(4) Uani d . (I) . . C 1
H1 .5488 .4912 .7526 .060 Uiso calc R (I) . . H 1
N2 .4518(2) .63423(14) .69366(13) .0398(3) Uani d . (I) . . N 1
C8 .2744(3) .64877(19) .66695(17) .0457(4) Uani d . (I) . . C 1
C9 .1658(3) .6001(2) .7481(2) .0602(5) Uani d . (I) . . C 1
H9A .0327 .5232 .6835 .060 Uiso calc R (I) . . H 1
H9B .1539 .6851 .8129 .060 Uiso calc R (I) . . H 1
C2 .5359(2) .68733(16) .61320(15) .0385(4) Uani d . (I) . . C 1
C7 .3954(3) .73205(18) .54034(17) .0443(4) Uani d . (I) . . C 1
N1 .2310(2) .70559(17) .57567(15) .0540(4) Uani d . (I) . . N 1
C3 .7104(3) .69867(18) .59514(16) .0440(4) Uani d . (I) . . C 1
H3 .8006 .6664 .6421 .060 Uiso calc R (I) . . H 1
C4 .7451(3) .76006(19) .50412(17) .0517(5) Uani d . (I) . . C 1
H4 .8619 .7695 .4903 .060 Uiso calc R (I) . . H 1
C5 .6111(3) .8086(2) .43187(18) .0534(5) Uani d . (I) . . C 1
C16 .6587(4) .8741(3) .3332(2) .0782(7) Uani d . (I) . . C 1
H16A .5762 .9279 .3138 .060 Uiso calc PR 0.60 . . H 0.60
H16B .6331 .7939 .2452 .060 Uiso calc PR 0.60 . . H 0.60
H16C .7971 .9421 .3779 .060 Uiso calc PR 0.60 . . H 0.60
H16D .7614 .8481 .3108 .060 Uiso calc PR 0.40 . . H 0.40
H16E .7045 .9821 .3794 .060 Uiso calc PR 0.40 . . H 0.40
H16F .5405 .8339 .2468 .060 Uiso calc PR 0.40 . . H 0.40
C6 .4349(3) .7931(2) .44925(18) .0552(5) Uani d . (I) . . C 1
H6 .3437 .8233 .4003 .060 Uiso calc R (I) . . H 1
C10 .7174(2) .69752(17) .92362(15) .0374(4) Uani d . (I) . . C 1
C11 .7434(3) .8425(2) 1.00688(18) .0497(5) Uani d . (I) . . C 1
F1 .58454(18) .88086(13) .97266(12) .0787(4) Uani d . (I) . . F 1
C12 .9178(3) .9474(2) 1.12085(18) .0599(5) Uani d . (I) . . C 1
H12 .9274 1.0431 1.1740 .060 Uiso calc R (I) . . H 1
C13 1.0780(3) .9086(2) 1.15499(19) .0603(5) Uani d . (I) . . C 1
H13 1.1977 .9786 1.2322 .060 Uiso calc R (I) . . H 1
C14 1.0641(3) .7668(2) 1.07622(18) .0545(5) Uani d . (I) . . C 1
H14 1.1730 .7402 1.0985 .060 Uiso calc R (I) . . H 1
C15 .8848(3) .66622(18) .96401(16) .0418(4) Uani d . (I) . . C 1
F2 .86969(16) .52610(11) .88627(11) .0591(3) Uani d . (I) . . F 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F .0171 .0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S .1246 .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 3 -2
-4 -1 1
-2 3 -4
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 95.38(8) yes
N2 C1 C10 112.95(13) ?
N2 C1 S 102.96(11) yes
C10 C1 S 113.93(11) ?
C8 N2 C2 107.32(13) yes
C8 N2 C1 120.61(14) yes
C2 N2 C1 131.91(14) yes
N1 C8 N2 114.16(16) yes
N1 C8 C9 131.41(17) ?
N2 C8 C9 114.41(15) yes
C8 C9 S 105.89(13) yes
C3 C2 N2 133.57(15) ?
C3 C2 C7 122.32(16) ?
N2 C2 C7 104.09(15) ?
C6 C7 N1 130.20(17) ?
C6 C7 C2 119.19(17) ?
N1 C7 C2 110.61(15) ?
C8 N1 C7 103.81(14) yes
C2 C3 C4 116.93(17) ?
C3 C4 C5 122.48(18) ?
C6 C5 C4 119.55(17) ?
C6 C5 C16 120.94(19) ?
C4 C5 C16 119.49(19) ?
C5 C6 C7 119.50(18) ?
C15 C10 C11 114.31(15) ?
C15 C10 C1 121.23(15) ?
C11 C10 C1 124.46(16) ?
F1 C11 C12 118.67(17) ?
F1 C11 C10 117.33(16) ?
C12 C11 C10 124.00(18) ?
C11 C12 C13 118.56(18) ?
C12 C13 C14 120.79(18) ?
C15 C14 C13 117.88(18) ?
F2 C15 C14 118.22(16) ?
F2 C15 C10 117.32(15) ?
C14 C15 C10 124.46(16) ?
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 . 1.8162(19) yes
S C1 . 1.8475(18) yes
C1 N2 . 1.452(2) yes
C1 C10 . 1.502(2) ?
N2 C8 . 1.355(2) yes
N2 C2 . 1.384(2) yes
C8 N1 . 1.309(2) yes
C8 C9 . 1.482(2) yes
C2 C3 . 1.380(2) ?
C2 C7 . 1.407(2) ?
C7 C6 . 1.389(3) ?
C7 N1 . 1.399(2) yes
C3 C4 . 1.380(2) ?
C4 C5 . 1.399(3) ?
C5 C6 . 1.384(3) ?
C5 C16 . 1.513(3) ?
C10 C15 . 1.379(2) ?
C10 C11 . 1.386(2) ?
C11 F1 . 1.356(2) ?
C11 C12 . 1.367(3) ?
C12 C13 . 1.368(3) ?
C13 C14 . 1.379(3) ?
C14 C15 . 1.370(2) ?
C15 F2 . 1.3585(19) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C1 H1 F2 .98 2.31 2.782(2) 108.6
C9 H9B F1 .97 2.95 3.225(3) 97.6
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
_geom_torsion_publ_flag
C9 S C1 N2 -7.82(12) ?
C9 S C1 C10 114.86(13) ?
C10 C1 N2 C8 -115.96(17) ?
S C1 N2 C8 7.37(17) ?
C10 C1 N2 C2 58.9(2) ?
S C1 N2 C2 -177.73(13) ?
C2 N2 C8 N1 .4(2) ?
C1 N2 C8 N1 176.44(14) ?
C2 N2 C8 C9 -178.56(14) ?
C1 N2 C8 C9 -2.5(2) ?
N1 C8 C9 S 177.33(17) ?
N2 C8 C9 S -3.92(19) ?
C1 S C9 C8 6.89(14) ?
C8 N2 C2 C3 -178.92(17) ?
C1 N2 C2 C3 5.7(3) ?
C8 N2 C2 C7 -.03(16) ?
C1 N2 C2 C7 -175.43(15) ?
C3 C2 C7 C6 -1.5(2) ?
N2 C2 C7 C6 179.45(14) ?
C3 C2 C7 N1 178.72(15) ?
N2 C2 C7 N1 -.32(17) ?
N2 C8 N1 C7 -.6(2) ?
C9 C8 N1 C7 178.17(18) ?
C6 C7 N1 C8 -179.19(17) ?
C2 C7 N1 C8 .56(19) ?
N2 C2 C3 C4 -179.68(15) ?
C7 C2 C3 C4 1.6(2) ?
C2 C3 C4 C5 -.3(2) ?
C3 C4 C5 C6 -1.1(3) ?
C3 C4 C5 C16 -179.71(15) ?
C4 C5 C6 C7 1.2(3) ?
C16 C5 C6 C7 179.79(15) ?
N1 C7 C6 C5 179.77(17) ?
C2 C7 C6 C5 .0(3) ?
N2 C1 C10 C15 -125.79(16) ?
S C1 C10 C15 117.18(15) ?
N2 C1 C10 C11 54.0(2) ?
S C1 C10 C11 -63.06(19) yes
C15 C10 C11 F1 179.85(15) ?
C1 C10 C11 F1 .1(2) ?
C15 C10 C11 C12 -.6(3) ?
C1 C10 C11 C12 179.58(17) ?
F1 C11 C12 C13 -179.87(17) ?
C10 C11 C12 C13 .6(3) ?
C11 C12 C13 C14 .0(3) ?
C12 C13 C14 C15 -.6(3) ?
C13 C14 C15 F2 -179.73(16) ?
C13 C14 C15 C10 .6(3) ?
C11 C10 C15 F2 -179.67(14) ?
C1 C10 C15 F2 .1(2) ?
C11 C10 C15 C14 .0(2) ?
C1 C10 C15 C14 179.82(15) ?
