#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/28/2222840.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_2222840
loop_
_publ_author_name
'Sharif, Shahzad'
'Khan, Islam Ullah'
'Arshad, Muhammad Nadeem'
'Sheikh, Tahir Ali'
'Qureshi, Muhammad Zahid'
_publ_section_title
;
 S-1,3-Benzothiazol-2-yl
 (2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)ethanethioate
;
_journal_coeditor_code           PV2172
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1805
_journal_paper_doi               10.1107/S1600536809025616
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C13 H10 N4 O2 S3'
_chemical_formula_moiety         'C13 H10 N4 O2 S3'
_chemical_formula_sum            'C13 H10 N4 O2 S3'
_chemical_formula_weight         350.43
_chemical_name_systematic
;
S-1,3-Benzothiazol-2-yl
(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)ethanethioate
;
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.001(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.9725(9)
_cell_length_b                   5.0156(3)
_cell_length_c                   21.7664(14)
_cell_measurement_reflns_used    2744
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.79
_cell_measurement_theta_min      2.37
_cell_volume                     1525.40(17)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics
'ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009)'
_computing_publication_material
;
WinGX (Farrugia, 1999) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_diffrn_measurement_method       'φ and ω'
_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  0.0538
_diffrn_reflns_av_sigmaI/netI    0.0678
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            16828
_diffrn_reflns_theta_full        28.44
_diffrn_reflns_theta_max         28.44
_diffrn_reflns_theta_min         1.46
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.497
_exptl_absorpt_correction_T_max  0.9720
_exptl_absorpt_correction_T_min  0.9412
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2007)'
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.526
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.345
_refine_diff_density_min         -0.340
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3829
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.1135
_refine_ls_R_factor_gt           0.0463
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0695P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1078
_refine_ls_wR_factor_ref         0.1449
_reflns_number_gt                2096
_reflns_number_total             3829
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            pv2172.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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 'Monoclinic' changed to 'monoclinic'
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 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2222840
_cod_database_fobs_code          2222840
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_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_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1 1.09909(5) 0.53325(15) 0.33403(3) 0.0473(2) Uani d . 1 . .
S S2 0.82219(5) 1.20705(16) 0.47275(4) 0.0481(2) Uani d . 1 . .
S S3 0.62042(6) 1.30442(19) 0.51641(4) 0.0658(3) Uani d . 1 . .
O O1 0.73807(14) 0.7981(4) 0.41758(10) 0.0515(6) Uani d . 1 . .
O O2 0.76884(15) 1.2729(4) 0.32595(10) 0.0599(6) Uani d . 1 . .
N N1 0.97196(15) 0.6544(4) 0.41510(10) 0.0342(5) Uani d . 1 . .
N N2 0.85575(16) 1.1371(5) 0.31772(11) 0.0457(6) Uani d . 1 . .
N N3 1.07870(17) 0.3179(5) 0.44609(11) 0.0508(7) Uani d . 1 . .
H H3A 1.0515 0.3001 0.4813 0.061 Uiso calc R 1 . .
H H3B 1.1273 0.2209 0.4368 0.061 Uiso calc R 1 . .
N N4 0.73303(16) 0.9626(5) 0.56704(11) 0.0468(6) Uani d . 1 . .
C C1 1.04521(18) 0.4975(5) 0.40561(12) 0.0352(6) Uani d . 1 . .
C C2 1.0159(2) 0.7693(5) 0.31617(13) 0.0428(7) Uani d . 1 . .
H H1 1.0129 0.8598 0.2789 0.051 Uiso calc R 1 . .
C C3 0.95521(18) 0.8065(5) 0.36329(12) 0.0340(6) Uani d . 1 . .
C C4 0.87134(19) 0.9811(5) 0.36324(12) 0.0370(6) Uani d . 1 . .
C C5 0.80041(19) 0.9594(5) 0.41574(13) 0.0379(7) Uani d . 1 . .
C C6 0.72758(19) 1.1345(6) 0.52336(14) 0.0427(7) Uani d . 1 . .
C C7 0.5768(2) 1.1236(6) 0.57791(14) 0.0516(8) Uani d . 1 . .
C C8 0.6472(2) 0.9518(6) 0.59907(14) 0.0451(7) Uani d . 1 . .
C C9 0.6272(2) 0.7821(7) 0.64769(16) 0.0641(10) Uani d . 1 . .
H H10 0.6733 0.6639 0.6622 0.077 Uiso calc R 1 . .
C C10 0.5376(3) 0.7925(8) 0.67398(17) 0.0729(11) Uani d . 1 . .
H H9 0.5232 0.6798 0.7066 0.088 Uiso calc R 1 . .
C C11 0.4697(3) 0.9652(8) 0.65302(19) 0.0755(11) Uani d . 1 . .
H H8 0.4099 0.9676 0.6719 0.091 Uiso calc R 1 . .
C C12 0.4867(2) 1.1338(8) 0.60535(19) 0.0762(11) Uani d . 1 . .
H H7 0.4400 1.2516 0.5916 0.091 Uiso calc R 1 . .
C C13 0.7520(3) 1.4460(6) 0.27606(16) 0.0641(10) Uani d . 1 . .
H H11A 0.8078 1.5537 0.2691 0.096 Uiso calc R 1 . .
H H11B 0.6985 1.5590 0.2852 0.096 Uiso calc R 1 . .
H H11C 0.7384 1.3431 0.2399 0.096 Uiso calc R 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'
N N 0.0061 0.0033 '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'
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
C2 S1 C1 . . 88.90(13) ?
C6 S2 C5 . . 99.42(13) ?
C7 S3 C6 . . 88.79(15) ?
N2 O2 C13 . . 110.1(2) ?
C1 N1 C3 . . 109.6(2) ?
C4 N2 O2 . . 110.2(2) ?
C1 N3 H3A . . 120.0 ?
C1 N3 H3B . . 120.0 ?
H3A N3 H3B . . 120.0 ?
C6 N4 C8 . . 110.3(2) ?
N1 C1 N3 . . 124.9(2) ?
N1 C1 S1 . . 114.7(2) ?
N3 C1 S1 . . 120.37(19) ?
C3 C2 S1 . . 110.7(2) ?
C3 C2 H1 . . 124.7 ?
S1 C2 H1 . . 124.7 ?
C2 C3 N1 . . 116.1(2) ?
C2 C3 C4 . . 126.0(2) ?
N1 C3 C4 . . 117.8(2) ?
N2 C4 C3 . . 120.2(2) ?
N2 C4 C5 . . 121.0(2) ?
C3 C4 C5 . . 118.7(2) ?
O1 C5 C4 . . 123.6(3) ?
O1 C5 S2 . . 125.2(2) ?
C4 C5 S2 . . 111.29(19) ?
N4 C6 S3 . . 116.5(2) ?
N4 C6 S2 . . 123.9(2) ?
S3 C6 S2 . . 119.61(18) ?
C8 C7 C12 . . 121.4(3) ?
C8 C7 S3 . . 109.5(2) ?
C12 C7 S3 . . 129.1(3) ?
C9 C8 C7 . . 119.5(3) ?
C9 C8 N4 . . 125.6(3) ?
C7 C8 N4 . . 115.0(3) ?
C10 C9 C8 . . 118.5(3) ?
C10 C9 H10 . . 120.8 ?
C8 C9 H10 . . 120.8 ?
C11 C10 C9 . . 121.2(4) ?
C11 C10 H9 . . 119.4 ?
C9 C10 H9 . . 119.4 ?
C12 C11 C10 . . 121.9(3) ?
C12 C11 H8 . . 119.1 ?
C10 C11 H8 . . 119.1 ?
C11 C12 C7 . . 117.5(4) ?
C11 C12 H7 . . 121.2 ?
C7 C12 H7 . . 121.2 ?
O2 C13 H11A . . 109.5 ?
O2 C13 H11B . . 109.5 ?
H11A C13 H11B . . 109.5 ?
O2 C13 H11C . . 109.5 ?
H11A C13 H11C . . 109.5 ?
H11B C13 H11C . . 109.5 ?
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 C2 . 1.704(3) ?
S1 C1 . 1.740(3) ?
S2 C6 . 1.759(3) ?
S2 C5 . 1.782(3) ?
S3 C7 . 1.728(3) ?
S3 C6 . 1.729(3) ?
O1 C5 . 1.190(3) ?
O2 N2 . 1.404(3) ?
O2 C13 . 1.410(4) ?
N1 C1 . 1.308(3) ?
N1 C3 . 1.382(3) ?
N2 C4 . 1.281(3) ?
N3 C1 . 1.344(3) ?
N3 H3A . 0.8600 ?
N3 H3B . 0.8600 ?
N4 C6 . 1.286(4) ?
N4 C8 . 1.388(3) ?
C2 C3 . 1.344(4) ?
C2 H1 . 0.9300 ?
C3 C4 . 1.463(4) ?
C4 C5 . 1.517(3) ?
C7 C8 . 1.387(4) ?
C7 C12 . 1.394(4) ?
C8 C9 . 1.387(4) ?
C9 C10 . 1.378(5) ?
C9 H10 . 0.9300 ?
C10 C11 . 1.364(5) ?
C10 H9 . 0.9300 ?
C11 C12 . 1.360(5) ?
C11 H8 . 0.9300 ?
C12 H7 . 0.9300 ?
C13 H11A . 0.9600 ?
C13 H11B . 0.9600 ?
C13 H11C . 0.9600 ?
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
_geom_hbond_publ_flag
N3 H3A N1 3_766 0.86 2.29 3.106(3) 158 yes
N3 H3B N4 3_766 0.86 2.16 2.997(3) 165 yes
C12 H7 O1 3_676 0.93 2.51 3.198(3) 131 yes
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
C13 O2 N2 C4 . . . . 179.6(3) ?
C3 N1 C1 N3 . . . . -177.9(3) ?
C3 N1 C1 S1 . . . . 1.6(3) ?
C2 S1 C1 N1 . . . . -1.1(2) ?
C2 S1 C1 N3 . . . . 178.4(2) ?
C1 S1 C2 C3 . . . . 0.3(2) ?
S1 C2 C3 N1 . . . . 0.6(3) ?
S1 C2 C3 C4 . . . . -176.0(2) ?
C1 N1 C3 C2 . . . . -1.4(3) ?
C1 N1 C3 C4 . . . . 175.5(2) ?
O2 N2 C4 C3 . . . . 176.5(2) ?
O2 N2 C4 C5 . . . . 0.7(4) ?
C2 C3 C4 N2 . . . . -7.4(4) ?
N1 C3 C4 N2 . . . . 176.1(2) ?
C2 C3 C4 C5 . . . . 168.5(3) ?
N1 C3 C4 C5 . . . . -8.1(4) ?
N2 C4 C5 O1 . . . . 92.6(3) ?
C3 C4 C5 O1 . . . . -83.3(3) ?
N2 C4 C5 S2 . . . . -86.7(3) ?
C3 C4 C5 S2 . . . . 97.4(2) ?
C6 S2 C5 O1 . . . . -1.4(3) ?
C6 S2 C5 C4 . . . . 177.9(2) ?
C8 N4 C6 S3 . . . . 0.8(3) ?
C8 N4 C6 S2 . . . . 179.6(2) ?
C7 S3 C6 N4 . . . . -0.9(3) ?
C7 S3 C6 S2 . . . . -179.7(2) ?
C5 S2 C6 N4 . . . . 87.6(3) ?
C5 S2 C6 S3 . . . . -93.60(19) ?
C6 S3 C7 C8 . . . . 0.7(2) ?
C6 S3 C7 C12 . . . . -179.4(4) ?
C12 C7 C8 C9 . . . . 1.4(5) ?
S3 C7 C8 C9 . . . . -178.6(3) ?
C12 C7 C8 N4 . . . . 179.6(3) ?
S3 C7 C8 N4 . . . . -0.4(3) ?
C6 N4 C8 C9 . . . . 177.9(3) ?
C6 N4 C8 C7 . . . . -0.3(4) ?
C7 C8 C9 C10 . . . . -0.8(5) ?
N4 C8 C9 C10 . . . . -178.8(3) ?
C8 C9 C10 C11 . . . . 0.0(6) ?
C9 C10 C11 C12 . . . . 0.2(6) ?
C10 C11 C12 C7 . . . . 0.4(6) ?
C8 C7 C12 C11 . . . . -1.2(6) ?
S3 C7 C12 C11 . . . . 178.8(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 4642899
