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#$Date: 2020-11-14 07:14:50 +0200 (Sat, 14 Nov 2020) $
#$Revision: 259139 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/36/2243676.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_2243676
loop_
_publ_author_name
'Khaldi, Hafsa'
'Djafri, Ahmed'
'Megrouss, Youcef'
'Khelloul, Nawel'
'Chouaih, Abdelkader'
'Djafri, Ayada'
_publ_section_title
;
 Molecular and crystal structure, Hirshfeld analysis and DFT investigation
 of 3-(furan-2-ylmethylidene)thiazolo[3,4-a]benzimidazole-1-thione
;
_journal_coeditor_code           WM5587
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              1832
_journal_page_last               1836
_journal_paper_doi               10.1107/S2056989020015017
_journal_volume                  76
_journal_year                    2020
_chemical_formula_iupac          'C14 H8 N2 O S2'
_chemical_formula_moiety         'C14 H8 N2 O S2'
_chemical_formula_sum            'C14 H8 N2 O S2'
_chemical_formula_weight         284.34
_chemical_name_systematic
;
3-(Furan-2-ylmethylidene)thiazolo[3,4-a]benzimidazole-1-thione
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 101.572(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.768(5)
_cell_length_b                   4.7583(15)
_cell_length_c                   17.316(6)
_cell_measurement_reflns_used    100
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      25.325
_cell_measurement_theta_min      1.953
_cell_volume                     1272.8(7)
_computing_cell_refinement
;
DENZO and SCALEPACK (Otwinowski & Minor, 1997)
;
_computing_data_collection
;
KappaCCD  (Nonius, 1998)
;
_computing_data_reduction
;
DENZO and SCALEPACK (Otwinowski & Minor, 1997)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012),
Mercury (Macrae et al.,  2020)
;
_computing_publication_material
;
SHELXL2014 (Sheldrick, 2015),
PLATON (Spek, 2020) and
publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       θ/2θ
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0198
_diffrn_reflns_av_unetI/netI     0.0194
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            10879
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.350
_diffrn_reflns_theta_min         3.580
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.409
_exptl_absorpt_correction_T_max  0.919
_exptl_absorpt_correction_T_min  0.856
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(Blessing, 1995)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.484
_exptl_crystal_description       prism
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.580
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.166
_refine_diff_density_min         -0.174
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.963
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2281
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.963
_refine_ls_R_factor_all          0.0707
_refine_ls_R_factor_gt           0.0515
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0089P)²+4.0499P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1033
_refine_ls_wR_factor_ref         0.1134
_reflns_number_gt                1835
_reflns_number_total             2281
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            wm5587sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2243676
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.897
_shelx_estimated_absorpt_t_max   0.963
loop_
_space_group_symop_operation_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'
loop_
_atom_site_type_symbol
_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_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1 0.01611(6) 0.1179(2) 0.89016(5) 0.0504(3) Uani d 1 . .
S S2 -0.14717(8) -0.2152(3) 0.85975(7) 0.0732(4) Uani d 1 . .
O O1 0.15244(16) 0.5043(6) 0.94349(14) 0.0523(7) Uani d 1 . .
C C14 0.0218(2) -0.4142(8) 0.67488(18) 0.0432(9) Uani d 1 . .
N N1 -0.01982(18) -0.2326(7) 0.77765(15) 0.0436(7) Uani d 1 . .
C C9 -0.0453(2) -0.4245(9) 0.71658(19) 0.0467(9) Uani d 1 . .
C C7 0.0587(2) -0.1218(8) 0.76838(19) 0.0427(9) Uani d 1 . .
C C11 -0.1192(3) -0.7634(9) 0.6302(2) 0.0536(10) Uani d 1 . .
H H11 -0.1661 -0.8825 0.6139 0.064 Uiso calc 1 . .
N N2 0.08686(18) -0.2264(7) 0.70874(15) 0.0430(7) Uani d 1 . .
C C8 -0.0552(2) -0.1294(9) 0.83946(19) 0.0467(9) Uani d 1 . .
C C13 0.0170(2) -0.5792(9) 0.60819(19) 0.0485(10) Uani d 1 . .
H H13 0.0595 -0.5718 0.5780 0.058 Uiso calc 1 . .
C C6 0.0923(2) 0.0822(8) 0.82795(19) 0.0430(9) Uani d 1 . .
C C5 0.1667(2) 0.2165(8) 0.8349(2) 0.0433(9) Uani d 1 . .
H H5 0.1996 0.1713 0.7976 0.052 Uiso calc 1 . .
C C3 0.2789(2) 0.5589(8) 0.9074(2) 0.0490(9) Uani d 1 . .
H H3 0.3240 0.5411 0.8804 0.059 Uiso calc 1 . .
C C10 -0.1160(2) -0.5960(9) 0.6964(2) 0.0503(10) Uani d 1 . .
H H10 -0.1595 -0.6002 0.7255 0.060 Uiso calc 1 . .
C C4 0.2034(2) 0.4222(8) 0.8920(2) 0.0462(9) Uani d 1 . .
C C1 0.2005(3) 0.6951(9) 0.9914(2) 0.0551(10) Uani d 1 . .
H H1 0.1822 0.7867 1.0326 0.066 Uiso calc 1 . .
C C2 0.2770(3) 0.7349(9) 0.9723(2) 0.0540(10) Uani d 1 . .
H H2 0.3206 0.8552 0.9969 0.065 Uiso calc 1 . .
C C12 -0.0534(3) -0.7544(9) 0.5885(2) 0.0574(11) Uani d 1 . .
H H12 -0.0568 -0.8722 0.5452 0.069 Uiso calc 1 . .
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'
O O 0.0106 0.0060 '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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C8 S1 C6 . . 94.40(17) ?
C1 O1 C4 . . 105.1(3) ?
C13 C14 C9 . . 119.3(4) ?
C13 C14 N2 . . 128.7(3) ?
C9 C14 N2 . . 112.0(3) ?
C7 N1 C8 . . 117.4(3) ?
C7 N1 C9 . . 106.9(3) ?
C8 N1 C9 . . 135.7(3) ?
C10 C9 N1 . . 132.9(3) ?
C10 C9 C14 . . 123.5(3) ?
N1 C9 C14 . . 103.6(3) ?
N2 C7 N1 . . 113.7(3) ?
N2 C7 C6 . . 133.7(3) ?
N1 C7 C6 . . 112.6(3) ?
C12 C11 C10 . . 120.5(4) ?
C12 C11 H11 . . 119.7 ?
C10 C11 H11 . . 119.7 ?
C7 N2 C14 . . 103.8(3) ?
N1 C8 S2 . . 126.5(3) ?
N1 C8 S1 . . 108.0(3) ?
S2 C8 S1 . . 125.5(2) ?
C12 C13 C14 . . 117.1(4) ?
C12 C13 H13 . . 121.4 ?
C14 C13 H13 . . 121.4 ?
C5 C6 C7 . . 125.8(3) ?
C5 C6 S1 . . 126.6(3) ?
C7 C6 S1 . . 107.6(3) ?
C6 C5 C4 . . 128.6(3) ?
C6 C5 H5 . . 115.7 ?
C4 C5 H5 . . 115.7 ?
C4 C3 C2 . . 106.7(3) ?
C4 C3 H3 . . 126.6 ?
C2 C3 H3 . . 126.6 ?
C9 C10 C11 . . 116.5(4) ?
C9 C10 H10 . . 121.8 ?
C11 C10 H10 . . 121.8 ?
C3 C4 O1 . . 110.3(3) ?
C3 C4 C5 . . 133.8(3) ?
O1 C4 C5 . . 115.9(3) ?
C2 C1 O1 . . 111.6(3) ?
C2 C1 H1 . . 124.2 ?
O1 C1 H1 . . 124.2 ?
C1 C2 C3 . . 106.3(4) ?
C1 C2 H2 . . 126.8 ?
C3 C2 H2 . . 126.8 ?
C13 C12 C11 . . 123.0(4) ?
C13 C12 H12 . . 118.5 ?
C11 C12 H12 . . 118.5 ?
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
S1 C8 . 1.739(4) ?
S1 C6 . 1.775(3) ?
S2 C8 . 1.612(4) ?
O1 C1 . 1.354(5) ?
O1 C4 . 1.372(4) ?
C14 C13 . 1.386(5) ?
C14 C9 . 1.397(5) ?
C14 N2 . 1.397(5) ?
N1 C7 . 1.384(4) ?
N1 C8 . 1.392(4) ?
N1 C9 . 1.394(5) ?
C9 C10 . 1.368(5) ?
C7 N2 . 1.302(4) ?
C7 C6 . 1.438(5) ?
C11 C12 . 1.378(5) ?
C11 C10 . 1.388(5) ?
C11 H11 . 0.9300 ?
C13 C12 . 1.376(6) ?
C13 H13 . 0.9300 ?
C6 C5 . 1.320(5) ?
C5 C4 . 1.429(5) ?
C5 H5 . 0.9300 ?
C3 C4 . 1.336(5) ?
C3 C2 . 1.407(5) ?
C3 H3 . 0.9300 ?
C10 H10 . 0.9300 ?
C1 C2 . 1.326(5) ?
C1 H1 . 0.9300 ?
C2 H2 . 0.9300 ?
C12 H12 . 0.9300 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C10 H10 S2 . 0.93 2.94 3.476(4) 118.5
C3 H3 N2 2_556 0.93 2.62 3.474(5) 153.6
C1 H1 S2 3_567 0.93 2.89 3.788(4) 162.7
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C7 N1 C9 C10 . . . . 179.5(4) ?
C8 N1 C9 C10 . . . . -3.1(7) ?
C7 N1 C9 C14 . . . . 0.3(4) ?
C8 N1 C9 C14 . . . . 177.7(4) ?
C13 C14 C9 C10 . . . . 1.7(6) ?
N2 C14 C9 C10 . . . . -178.7(3) ?
C13 C14 C9 N1 . . . . -179.0(3) ?
N2 C14 C9 N1 . . . . 0.6(4) ?
C8 N1 C7 N2 . . . . -179.2(3) ?
C9 N1 C7 N2 . . . . -1.2(4) ?
C8 N1 C7 C6 . . . . 1.8(5) ?
C9 N1 C7 C6 . . . . 179.7(3) ?
N1 C7 N2 C14 . . . . 1.5(4) ?
C6 C7 N2 C14 . . . . -179.7(4) ?
C13 C14 N2 C7 . . . . 178.2(4) ?
C9 C14 N2 C7 . . . . -1.3(4) ?
C7 N1 C8 S2 . . . . 177.2(3) ?
C9 N1 C8 S2 . . . . 0.0(6) ?
C7 N1 C8 S1 . . . . -1.2(4) ?
C9 N1 C8 S1 . . . . -178.4(3) ?
C6 S1 C8 N1 . . . . 0.3(3) ?
C6 S1 C8 S2 . . . . -178.1(3) ?
C9 C14 C13 C12 . . . . -2.5(5) ?
N2 C14 C13 C12 . . . . 178.0(4) ?
N2 C7 C6 C5 . . . . -0.5(7) ?
N1 C7 C6 C5 . . . . 178.3(4) ?
N2 C7 C6 S1 . . . . 179.8(4) ?
N1 C7 C6 S1 . . . . -1.4(4) ?
C8 S1 C6 C5 . . . . -179.0(4) ?
C8 S1 C6 C7 . . . . 0.7(3) ?
C7 C6 C5 C4 . . . . 179.5(4) ?
S1 C6 C5 C4 . . . . -0.9(6) ?
N1 C9 C10 C11 . . . . -179.7(4) ?
C14 C9 C10 C11 . . . . -0.7(6) ?
C12 C11 C10 C9 . . . . 0.5(6) ?
C2 C3 C4 O1 . . . . 0.7(4) ?
C2 C3 C4 C5 . . . . -179.5(4) ?
C1 O1 C4 C3 . . . . -0.6(4) ?
C1 O1 C4 C5 . . . . 179.5(3) ?
C6 C5 C4 C3 . . . . 175.6(4) ?
C6 C5 C4 O1 . . . . -4.5(6) ?
C4 O1 C1 C2 . . . . 0.2(4) ?
O1 C1 C2 C3 . . . . 0.2(5) ?
C4 C3 C2 C1 . . . . -0.5(5) ?
C14 C13 C12 C11 . . . . 2.4(6) ?
C10 C11 C12 C13 . . . . -1.4(6) ?

_cod_database_fobs_code 2243676
