#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/96/2209696.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_2209696
loop_
_publ_author_name
'Odabaşoğlu, Mustafa'
'Büyükgüngör, Orhan'
_publ_section_title
;
 3-(Thiazol-2-ylamino)isobenzofuran-1(3H)-one
;
_journal_coeditor_code           WW2023
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2866
_journal_page_last               o2868
_journal_paper_doi               10.1107/S1600536806022574
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C11 H8 N2 O2 S'
_chemical_formula_moiety         'C11 H8 N2 O2 S'
_chemical_formula_sum            'C11 H8 N2 O2 S'
_chemical_formula_weight         232.25
_chemical_name_common            3-(2-thiazolylamino)phthalide
_chemical_name_systematic
;
3-(thiazol-2-ylamino)isobenzofuran-1(3H)-one
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   14.2910(10)
_cell_length_b                   8.6990(10)
_cell_length_c                   17.5290(10)
_cell_measurement_reflns_used    14575
_cell_measurement_temperature    296
_cell_measurement_theta_max      27.96
_cell_measurement_theta_min      2.33
_cell_volume                     2179.2(3)
_computing_cell_refinement       X-AREA
_computing_data_collection       'X-AREA (Stoe, 2002)'
_computing_data_reduction        'X-RED32 (Stoe, 2002)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Stoe IPDS-2'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_source
'       'sealed X-ray tube, 12 x 0.4 mm long-fine focus''
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0538
_diffrn_reflns_av_sigmaI/netI    0.0320
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            14575
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.32
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.29
_exptl_absorpt_correction_T_max  0.9603
_exptl_absorpt_correction_T_min  0.8526
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   '(X-RED32; Stoe, 2002)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.74
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.155
_refine_diff_density_min         -0.212
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     149
_refine_ls_number_reflns         2145
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0580
_refine_ls_R_factor_gt           0.0400
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0576P)²+0.2248P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0986
_refine_ls_wR_factor_ref         0.1061
_reflns_number_gt                1579
_reflns_number_total             2145
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ww2023.cif
_cod_data_source_block           I
_cod_original_sg_symbol_Hall     '-P 2ac 2 ab'
_cod_database_code               2209696
_cod_database_fobs_code          2209696
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, 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
C C1 0.44292(17) 0.3454(4) 0.55101(14) 0.0881(8) Uani d . 1
C C2 0.40682(14) 0.2524(3) 0.48790(11) 0.0632(5) Uani d . 1
C C3 0.45359(17) 0.1588(4) 0.43688(14) 0.0871(8) Uani d . 1
H H3 0.5183 0.1482 0.4389 0.104 Uiso calc R 1
C C4 0.4020(2) 0.0826(3) 0.38359(14) 0.0814(7) Uani d . 1
H H4 0.4319 0.0190 0.3486 0.098 Uiso calc R 1
C C5 0.30667(18) 0.0986(3) 0.38109(12) 0.0678(6) Uani d . 1
H H5 0.2729 0.0457 0.3441 0.081 Uiso calc R 1
C C6 0.25965(14) 0.1915(2) 0.43209(11) 0.0572(5) Uani d . 1
H H6 0.1950 0.2026 0.4299 0.069 Uiso calc R 1
C C7 0.31182(13) 0.2671(2) 0.48635(10) 0.0487(4) Uani d . 1
C C8 0.28252(13) 0.3705(2) 0.55056(10) 0.0532(5) Uani d . 1
H H8 0.2515 0.4620 0.5300 0.064 Uiso calc R 1
C C9 0.17996(12) 0.3814(2) 0.65944(10) 0.0488(4) Uani d . 1
C C10 0.08888(16) 0.4724(3) 0.76639(13) 0.0753(7) Uani d . 1
H H10 0.0526 0.4906 0.8095 0.090 Uiso calc R 1
C C11 0.12446(15) 0.5799(3) 0.72203(13) 0.0692(6) Uani d . 1
H H11 0.1146 0.6838 0.7315 0.083 Uiso calc R 1
N N1 0.22248(12) 0.29647(17) 0.60348(9) 0.0519(4) Uani d . 1
N N2 0.17718(12) 0.53016(18) 0.66072(9) 0.0577(4) Uani d . 1
O O1 0.52223(13) 0.3622(4) 0.57194(13) 0.1479(11) Uani d . 1
O O2 0.37087(11) 0.4144(2) 0.58646(9) 0.0782(5) Uani d . 1
S S1 0.11938(4) 0.29357(7) 0.73281(3) 0.0703(2) Uani d . 1
H H1 0.2423(15) 0.207(3) 0.6180(12) 0.065(6) Uiso d . 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
_geom_angle_publ_flag
O1 C1 O2 121.8(2) y
O1 C1 C2 129.1(3) y
O2 C1 C2 109.04(19) ?
C7 C2 C3 121.6(2) ?
C7 C2 C1 108.30(19) ?
C3 C2 C1 130.1(2) ?
C4 C3 C2 118.0(2) ?
C4 C3 H3 121.0 ?
C2 C3 H3 121.0 ?
C3 C4 C5 120.7(2) ?
C3 C4 H4 119.7 ?
C5 C4 H4 119.7 ?
C4 C5 C6 121.5(2) ?
C4 C5 H5 119.2 ?
C6 C5 H5 119.2 ?
C7 C6 C5 117.65(19) ?
C7 C6 H6 121.2 ?
C5 C6 H6 121.2 ?
C2 C7 C6 120.54(18) ?
C2 C7 C8 108.61(16) ?
C6 C7 C8 130.85(18) ?
N1 C8 O2 111.09(15) y
N1 C8 C7 112.81(15) ?
O2 C8 C7 103.81(15) ?
N1 C8 H8 109.7 ?
O2 C8 H8 109.7 ?
C7 C8 H8 109.7 ?
N2 C9 N1 124.40(16) ?
N2 C9 S1 114.44(14) ?
N1 C9 S1 121.08(13) ?
C11 C10 S1 110.00(17) ?
C11 C10 H10 125.0 ?
S1 C10 H10 125.0 ?
C10 C11 N2 116.5(2) ?
C10 C11 H11 121.7 ?
N2 C11 H11 121.7 ?
C9 N1 C8 119.45(15) ?
C9 N1 H1 114.8(14) ?
C8 N1 H1 113.7(15) ?
C9 N2 C11 110.07(17) ?
C1 O2 C8 110.22(15) ?
C10 S1 C9 88.94(10) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 O1 1.200(3) y
C1 O2 1.344(3) y
C1 C2 1.464(3) ?
C2 C7 1.364(3) y
C2 C3 1.382(3) ?
C3 C4 1.362(4) ?
C3 H3 0.9300 ?
C4 C5 1.371(4) ?
C4 H4 0.9300 ?
C5 C6 1.380(3) ?
C5 H5 0.9300 ?
C6 C7 1.376(3) ?
C6 H6 0.9300 ?
C7 C8 1.500(2) y
C8 N1 1.418(2) y
C8 O2 1.462(2) ?
C8 H8 0.9800 ?
C9 N2 1.295(2) y
C9 N1 1.370(2) y
C9 S1 1.7285(18) y
C10 C11 1.318(3) ?
C10 S1 1.720(3) y
C10 H10 0.9300 ?
C11 N2 1.382(2) ?
C11 H11 0.9300 ?
N1 H1 0.87(2) ?
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
N1 H1 N2 7_655 0.87(2) 2.06(2) 2.903(2) 164(2)
C6 H6 O1 3_456 0.93 2.53 3.426(3) 161
C10 H10 O1 6_557 0.93 2.40 3.140(3) 137
C4 H4 Cg1 3_556 0.93 3.120 3.749(3) 126.48
C5 H5 Cg1 8_554 0.93 3.064 3.896(2) 149.78
C8 H8 Cg2 7_555 0.98 2.934 3.888(2) 163.90
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
O1 C1 C2 C7 179.2(4)
O2 C1 C2 C7 -0.1(3)
O1 C1 C2 C3 1.0(6)
O2 C1 C2 C3 -178.3(3)
C7 C2 C3 C4 1.0(4)
C1 C2 C3 C4 179.1(3)
C2 C3 C4 C5 -0.1(4)
C3 C4 C5 C6 -0.2(4)
C4 C5 C6 C7 -0.5(3)
C3 C2 C7 C6 -1.7(3)
C1 C2 C7 C6 179.9(2)
C3 C2 C7 C8 177.6(2)
C1 C2 C7 C8 -0.9(3)
C5 C6 C7 C2 1.4(3)
C5 C6 C7 C8 -177.68(19)
C2 C7 C8 N1 -118.95(19)
C6 C7 C8 N1 60.2(3)
C2 C7 C8 O2 1.4(2)
C6 C7 C8 O2 -179.43(19)
S1 C10 C11 N2 -0.4(3)
N2 C9 N1 C8 12.4(3)
S1 C9 N1 C8 -171.02(14)
O2 C8 N1 C9 72.6(2)
C7 C8 N1 C9 -171.33(16)
N1 C9 N2 C11 176.40(18)
S1 C9 N2 C11 -0.4(2)
C10 C11 N2 C9 0.5(3)
O1 C1 O2 C8 -178.4(3)
C2 C1 O2 C8 1.0(3)
N1 C8 O2 C1 120.1(2)
C7 C8 O2 C1 -1.4(2)
C11 C10 S1 C9 0.19(19)
N2 C9 S1 C10 0.10(17)
N1 C9 S1 C10 -176.77(17)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 573774
