#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/20/43/7204346.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7204346
loop_
_publ_author_name
'Landreau, Cyrille'
'Deniaud, David'
'Evain, Michel'
'Reliquet, Alain'
'Meslin, Jean-Claude'
_publ_section_title
;
 Efficient regioselective synthesis of triheterocyclic compounds:
 imidazo[2,1-b]benzothiazoles, pyrimido[2,1-b]benzothiazolones and
 pyrimido[2,1-b]benzothiazoles
;
_journal_issue                   6
_journal_name_full
'Journal of the Chemical Society, Perkin Transactions 1'
_journal_page_first              741
_journal_paper_doi               10.1039/b111639h
_journal_year                    2002
_chemical_formula_moiety         'C12 H10 N2 O2 S'
_chemical_formula_sum            'C12 H10 N2 O2 S'
_chemical_formula_weight         246.3
_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
_cell_angle_beta                 150.686(15)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.4765(18)
_cell_length_b                   11.1064(9)
_cell_length_c                   14.5268(18)
_cell_volume                     1143.5(6)
_diffrn_measurement_device_type  'Nonius CAD4F and Stoe IPDS'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0494
_diffrn_reflns_av_sigmaI/netI    0.1958
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            13223
_diffrn_reflns_theta_max         29.99
_diffrn_reflns_theta_min         2.34
_diffrn_standards_decay_%        1
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.273
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  1.000
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.43
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.40
_refine_diff_density_min         -0.27
_refine_ls_extinction_coef       0.13(3)
_refine_ls_extinction_method     'B-C type 1 Gaussian isotropic'
_refine_ls_goodness_of_fit_obs   0.99
_refine_ls_goodness_of_fit_ref   0.85
_refine_ls_number_parameters     155
_refine_ls_number_reflns         3337
_refine_ls_R_factor_all          0.2261
_refine_ls_R_factor_gt           0.0487
_refine_ls_shift/su_max          0.0001
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     w=1/(σ²(I)+0.001024I²)
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_gt          0.0681
_refine_ls_wR_factor_ref         0.1128
_reflns_limit_h_max              0
_reflns_limit_h_min              -20
_reflns_limit_k_max              15
_reflns_limit_k_min              0
_reflns_limit_l_max              20
_reflns_limit_l_min              -9
_reflns_number_observed          999
_reflns_number_total             3337
_reflns_observed_criterion       2
_cod_data_source_file            b111639h.txt
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:
'_diffrn_radiation_probe' value 'X-ray' changed to 'x-ray' 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 
;
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               7204346
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,1/2+y,1/2-z
3 -x,-y,-z
4 x,1/2-y,1/2+z
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_adp_type
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_symmetry_multiplicity
_atom_site_occupancy
N1 N Uani 0.1779(4) 0.6359(3) 0.3752(4) 0.062(7) 4 1
C2 C Uani 0.2737(5) 0.7006(3) 0.3931(5) 0.058(8) 4 1
C3 C Uani 0.3021(4) 0.6379(3) 0.3385(4) 0.043(6) 4 1
N4 N Uani 0.2194(3) 0.5261(3) 0.2830(3) 0.042(5) 4 1
C4a C Uani 0.1861(4) 0.4148(3) 0.2102(4) 0.041(6) 4 1
C5 C Uani 0.2384(4) 0.3768(3) 0.1691(4) 0.048(7) 4 1
C6 C Uani 0.1899(5) 0.2627(3) 0.0997(5) 0.060(8) 4 1
C7 C Uani 0.0903(5) 0.1867(3) 0.0706(5) 0.065(8) 4 1
C8 C Uani 0.0369(5) 0.2232(3) 0.1105(5) 0.059(7) 4 1
C8a C Uani 0.0856(4) 0.3380(3) 0.1812(4) 0.048(7) 4 1
S9 S Uani 0.03373(13) 0.40270(9) 0.24271(13) 0.060(2) 4 1
C9a C Uani 0.1486(5) 0.5326(3) 0.3086(5) 0.050(7) 4 1
C10 C Uani 0.3941(4) 0.6755(3) 0.3340(4) 0.047(7) 4 1
C11 C Uani 0.5207(5) 0.8461(3) 0.3681(5) 0.063(8) 4 1
C12 C Uani 0.5246(8) 0.9752(4) 0.3832(8) 0.118(17) 4 1
O1 O Uani 0.4311(3) 0.6146(2) 0.3009(3) 0.066(6) 4 1
O2 O Uani 0.4339(3) 0.7931(2) 0.3733(3) 0.059(5) 4 1
H2 H Uiso 0.3181 0.783512 0.4404 0.0577 4 1
H5 H Uiso 0.3098 0.429974 0.1893 0.0479 4 1
H6 H Uiso 0.2281 0.235367 0.0714 0.0601 4 1
H7 H Uiso 0.0554 0.105788 0.0190 0.0650 4 1
H8 H Uiso -0.0331 0.168862 0.0905 0.0586 4 1
H11a H Uiso 0.4475 0.824571 0.2496 0.0625 4 1
H11b H Uiso 0.6498 0.815733 0.4738 0.0625 4 1
H12a H Uiso 0.3949 1.0033 0.2798 0.1183 4 1
H12b H Uiso 0.5789 1.015269 0.3764 0.1183 4 1
H12c H Uiso 0.6003 0.993855 0.5035 0.1183 4 1
loop_
_atom_type_symbol
_atom_type_oxidation_number
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
_atom_type_scat_versus_stol_list
S 0 0.000 0.000 'International Tables Vol C Tables  4.2.6.8 and 6.1.1.1'
;
stol      0.00    0.05    0.10    0.15    0.20    0.25    0.30    0.35    0.40  
f      16.000  15.484  14.177  12.583  11.109   9.927   9.039   8.376   7.856  
stol      0.45    0.50    0.55    0.60    0.65    0.70    0.75    0.80    0.85  
f       7.417   7.017   6.633   6.254   5.877   5.505   5.141   4.790   4.454  
stol      0.90    0.95    1.00    1.05    1.10    1.15    1.20    1.25    1.30  
f       4.138   3.842   3.570   3.320   3.092   2.885   2.699   2.533   2.384  
stol      1.35    1.40    1.45    1.50    1.55    1.60    1.65    1.70    1.75  
f       2.251   2.133   2.028   1.935   1.853   1.779   1.713   1.655   1.604  
;
N 0 0.006 0.003 'International Tables Vol C Tables  4.2.6.8 and 6.1.1.1'
;
stol      0.00    0.05    0.10    0.15    0.20    0.25    0.30    0.35    0.40  
f       7.000   6.776   6.180   5.385   4.563   3.825   3.219   2.747   2.393  
stol      0.45    0.50    0.55    0.60    0.65    0.70    0.75    0.80    0.85  
f       2.132   1.942   1.802   1.697   1.616   1.551   1.496   1.445   1.398  
stol      0.90    0.95    1.00    1.05    1.10    1.15    1.20    1.25    1.30  
f       1.353   1.309   1.265   1.221   1.177   1.133   1.090   1.047   1.004  
stol      1.35    1.40    1.45    1.50    1.55    1.60    1.65    1.70    1.75  
f       0.962   0.921   0.882   0.843   0.805   0.769   0.734   0.700   0.667  
;
O 0 0.011 0.006 'International Tables Vol C Tables  4.2.6.8 and 6.1.1.1'
;
stol      0.00    0.05    0.10    0.15    0.20    0.25    0.30    0.35    0.40  
f       8.000   7.798   7.245   6.472   5.623   4.808   4.089   3.489   3.006  
stol      0.45    0.50    0.55    0.60    0.65    0.70    0.75    0.80    0.85  
f       2.629   2.338   2.115   1.946   1.816   1.714   1.635   1.568   1.512  
stol      0.90    0.95    1.00    1.05    1.10    1.15    1.20    1.25    1.30  
f       1.463   1.419   1.377   1.337   1.298   1.259   1.221   1.183   1.145  
stol      1.35    1.40    1.45    1.50    1.55    1.60    1.65    1.70    1.75  
f       1.107   1.070   1.033   0.997   0.961   0.926   0.891   0.857   0.824  
;
C 0 0.003 0.002 'International Tables Vol C Tables  4.2.6.8 and 6.1.1.1'
;
stol      0.00    0.05    0.10    0.15    0.20    0.25    0.30    0.35    0.40  
f       6.000   5.749   5.107   4.311   3.560   2.949   2.494   2.171   1.948  
stol      0.45    0.50    0.55    0.60    0.65    0.70    0.75    0.80    0.85  
f       1.794   1.685   1.603   1.537   1.479   1.426   1.374   1.322   1.271  
stol      0.90    0.95    1.00    1.05    1.10    1.15    1.20    1.25    1.30  
f       1.219   1.166   1.114   1.063   1.012   0.962   0.914   0.867   0.822  
stol      1.35    1.40    1.45    1.50    1.55    1.60    1.65    1.70    1.75  
f       0.778   0.736   0.697   0.659   0.622   0.588   0.556   0.525   0.495  
;
H 0 0.000 0.000 'International Tables Vol C Tables  4.2.6.8 and 6.1.1.1'
;
stol      0.00    0.05    0.10    0.15    0.20    0.25    0.30    0.35    0.40  
f       1.000   0.960   0.854   0.713   0.568   0.438   0.331   0.248   0.184  
stol      0.45    0.50    0.55    0.60    0.65    0.70    0.75    0.80    0.85  
f       0.138   0.103   0.078   0.060   0.046   0.036   0.028   0.022   0.018  
stol      0.90    0.95    1.00    1.05    1.10    1.15    1.20    1.25    1.30  
f       0.014   0.011   0.009   0.007   0.006   0.005   0.004   0.004   0.003  
stol      1.35    1.40    1.45    1.50    1.55    1.60    1.65    1.70    1.75  
f       0.003   0.002   0.002   0.002   0.002   0.002   0.001   0.001   0.000  
;
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
C2 N1 C9a 102.8(7) . . .
N1 C2 C3 113.0(4) . . .
N1 C2 H2 124.1 . . .
C3 C2 H2 122.8 . . .
C2 C3 N4 104.4(6) . . .
C2 C3 C10 129.4(4) . . .
N4 C3 C10 126.1(5) . . .
C3 N4 C4a 140.7(6) . . .
C3 N4 C9a 105.4(4) . . .
C4a N4 C9a 113.8(4) . . .
N4 C4a C5 129.5(5) . . .
N4 C4a C8a 110.3(6) . . .
C5 C4a C8a 120.2(4) . . .
C4a C5 C6 118.6(6) . . .
C4a C5 H5 121.1 . . .
C6 C5 H5 120.3 . . .
C5 C6 C7 121.2(8) . . .
C5 C6 H6 118.6 . . .
C7 C6 H6 120.1 . . .
C6 C7 C8 120.9(4) . . .
C6 C7 H7 119.9 . . .
C8 C7 H7 119.3 . . .
C7 C8 C8a 118.4(6) . . .
C7 C8 H8 120.7 . . .
C8a C8 H8 120.8 . . .
C4a C8a C8 120.6(7) . . .
C4a C8a S9 113.2(3) . . .
C8 C8a S9 126.2(6) . . .
C8a S9 C9a 89.5(3) . . .
N1 C9a N4 114.3(6) . . .
N1 C9a S9 132.5(8) . . .
N4 C9a S9 113.2(4) . . .
C3 C10 O1 127.4(4) . . .
C3 C10 O2 109.4(5) . . .
O1 C10 O2 123.2(6) . . .
C12 C11 O2 108.4(8) . . .
C12 C11 H11a 110.4 . . .
C12 C11 H11b 109.6 . . .
O2 C11 H11a 109.5 . . .
O2 C11 H11b 109.5 . . .
H11a C11 H11b 109.4 . . .
C11 C12 H12a 108.3 . . .
C11 C12 H12b 111.4 . . .
C11 C12 H12c 108.4 . . .
H12a C12 H12b 109.5 . . .
H12a C12 H12c 109.6 . . .
H12b C12 H12c 109.6 . . .
C10 O2 C11 116.4(5) . . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
N1 C2 1.371(10) . .
N1 C9a 1.310(7) . .
C2 C3 1.361(11) . .
C2 H2 0.982 . .
C3 N4 1.393(5) . .
C3 C10 1.451(11) . .
N4 C4a 1.411(6) . .
N4 C9a 1.363(12) . .
C4a C5 1.377(11) . .
C4a C8a 1.398(9) . .
C5 C6 1.371(5) . .
C5 H5 0.987 . .
C6 C7 1.381(11) . .
C6 H6 0.982 . .
C7 C8 1.371(14) . .
C7 H7 0.982 . .
C8 C8a 1.384(5) . .
C8 H8 0.981 . .
C8a S9 1.746(8) . .
S9 C9a 1.729(5) . .
C10 O1 1.194(9) . .
C10 O2 1.338(4) . .
C11 C12 1.444(6) . .
C11 O2 1.448(10) . .
C11 H11a 0.981 . .
C11 H11b 0.980 . .
C12 H12a 0.980 . .
C12 H12b 0.980 . .
C12 H12c 0.979 . .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9065461
