#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/27/2222710.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_2222710
loop_
_publ_author_name
'Penthala, Narsimha Reddy'
'Reddy, Thirupathi Reddy Yerram'
'Parkin, Sean'
'Crooks, Peter A.'
_publ_section_title
rac-2-(2-Amino-4-oxo-4,5-dihydro-1,3-thiazol-5-yl)-2-hydroxyindane-1,3-dione
_journal_coeditor_code           HG2529
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1877
_journal_paper_doi               10.1107/S1600536809025574
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C12 H8 N2 O4 S'
_chemical_formula_moiety         'C12 H8 N2 O4 S'
_chemical_formula_sum            'C12 H8 N2 O4 S'
_chemical_formula_weight         276.26
_chemical_name_systematic
;
rac-2-(2-amino-4-oxo-4,5-dihydro-1,3-thiazol-5-yl)-2-hydroxyindane-
1,3-dione
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 114.0171(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.1702(2)
_cell_length_b                   5.67130(10)
_cell_length_c                   14.8296(3)
_cell_measurement_reflns_used    2750
_cell_measurement_temperature    90.0(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.00
_cell_volume                     1088.58(3)
_computing_cell_refinement       'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1998)'
_computing_data_reduction        'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'XP in SHELXTL (Sheldrick, 2008)'
_computing_publication_material
;
SHELXL97 (Sheldrick, 2008) and local procedures
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      90.0(2)
_diffrn_detector_area_resol_mean 9.1
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'ω scans at fixed χ = 55°'
_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  0.0350
_diffrn_reflns_av_sigmaI/netI    0.0238
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            23811
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         1.68
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.310
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_correction_T_min  0.927
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SCALEPACK; Otwinowski & Minor, 1997)'
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.686
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       tablet
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.376
_refine_diff_density_min         -0.262
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2498
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0328
_refine_ls_R_factor_gt           0.0290
_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)+(0.0342P)²+0.6796P], where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0737
_refine_ls_wR_factor_ref         0.0760
_reflns_number_gt                2268
_reflns_number_total             2498
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hg2529.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2222710
_cod_database_fobs_code          2222710
loop_
_symmetry_equiv_pos_as_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_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1 0.66382(2) 0.49412(5) 0.17138(2) 0.01284(10) Uani d . 1 . .
O O1 0.42723(7) 0.96668(16) 0.23512(7) 0.0153(2) Uani d . 1 . .
N N1 0.49352(8) 0.24974(19) 0.06881(8) 0.0125(2) Uani d . 1 . .
C C1 0.45157(9) 0.7729(2) 0.27136(9) 0.0120(2) Uani d . 1 . .
O O2 0.63896(6) 0.76852(16) 0.33559(7) 0.01299(19) Uani d . 1 . .
H H2 0.6250 0.9129 0.3335 0.019 Uiso calc R 1 . .
N N2 0.64515(8) 0.0977(2) 0.06834(8) 0.0143(2) Uani d . 1 . .
H H2A 0.6112 -0.0200 0.0303 0.017 Uiso calc R 1 . .
H H2B 0.7125 0.1084 0.0878 0.017 Uiso calc R 1 . .
C C2 0.54859(9) 0.6411(2) 0.27535(9) 0.0111(2) Uani d . 1 . .
O O3 0.61330(7) 0.25829(17) 0.35097(7) 0.0167(2) Uani d . 1 . .
C C3 0.54791(9) 0.4118(2) 0.33094(9) 0.0120(2) Uani d . 1 . .
O O4 0.37082(7) 0.45803(17) 0.10054(7) 0.0162(2) Uani d . 1 . .
C C4 0.45890(10) 0.4216(2) 0.35841(9) 0.0127(2) Uani d . 1 . .
C C5 0.42889(10) 0.2577(2) 0.41132(9) 0.0153(3) Uani d . 1 . .
H H5 0.4654 0.1135 0.4326 0.018 Uiso calc R 1 . .
C C6 0.34424(10) 0.3100(3) 0.43217(9) 0.0178(3) Uani d . 1 . .
H H6 0.3220 0.1996 0.4676 0.021 Uiso calc R 1 . .
C C7 0.29109(10) 0.5234(3) 0.40164(10) 0.0180(3) Uani d . 1 . .
H H7 0.2348 0.5578 0.4186 0.022 Uiso calc R 1 . .
C C8 0.31936(10) 0.6860(3) 0.34679(9) 0.0158(3) Uani d . 1 . .
H H8 0.2823 0.8293 0.3248 0.019 Uiso calc R 1 . .
C C9 0.40390(9) 0.6314(2) 0.32529(9) 0.0130(2) Uani d . 1 . .
C C10 0.54450(9) 0.6061(2) 0.17129(9) 0.0116(2) Uani d . 1 . .
H H10 0.5296 0.7620 0.1368 0.014 Uiso calc R 1 . .
C C11 0.45938(9) 0.4304(2) 0.10930(9) 0.0121(2) Uani d . 1 . .
C C12 0.59513(9) 0.2577(2) 0.09614(9) 0.0121(2) Uani 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C12 S1 C10 . . 89.51(6) ?
C12 N1 C11 . . 111.88(11) ?
O1 C1 C9 . . 128.58(12) ?
O1 C1 C2 . . 123.02(11) ?
C9 C1 C2 . . 108.20(10) ?
C2 O2 H2 . . 109.5 ?
C12 N2 H2A . . 120.0 ?
C12 N2 H2B . . 120.0 ?
H2A N2 H2B . . 120.0 ?
O2 C2 C10 . . 110.66(10) ?
O2 C2 C3 . . 107.00(9) ?
C10 C2 C3 . . 115.04(10) ?
O2 C2 C1 . . 109.71(10) ?
C10 C2 C1 . . 110.82(10) ?
C3 C2 C1 . . 103.28(10) ?
O3 C3 C4 . . 127.68(12) ?
O3 C3 C2 . . 124.33(11) ?
C4 C3 C2 . . 107.91(10) ?
C5 C4 C9 . . 120.86(12) ?
C5 C4 C3 . . 128.50(12) ?
C9 C4 C3 . . 110.63(11) ?
C6 C5 C4 . . 118.26(12) ?
C6 C5 H5 . . 120.9 ?
C4 C5 H5 . . 120.9 ?
C5 C6 C7 . . 120.88(12) ?
C5 C6 H6 . . 119.6 ?
C7 C6 H6 . . 119.6 ?
C8 C7 C6 . . 121.13(12) ?
C8 C7 H7 . . 119.4 ?
C6 C7 H7 . . 119.4 ?
C7 C8 C9 . . 117.69(13) ?
C7 C8 H8 . . 121.2 ?
C9 C8 H8 . . 121.2 ?
C8 C9 C4 . . 121.14(12) ?
C8 C9 C1 . . 128.92(12) ?
C4 C9 C1 . . 109.91(11) ?
C2 C10 C11 . . 112.48(10) ?
C2 C10 S1 . . 113.13(8) ?
C11 C10 S1 . . 106.11(8) ?
C2 C10 H10 . . 108.3 ?
C11 C10 H10 . . 108.3 ?
S1 C10 H10 . . 108.3 ?
O4 C11 N1 . . 125.52(12) ?
O4 C11 C10 . . 120.08(11) ?
N1 C11 C10 . . 114.40(10) ?
N2 C12 N1 . . 122.39(12) ?
N2 C12 S1 . . 119.58(9) ?
N1 C12 S1 . . 118.02(10) ?
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 C12 . 1.7623(13) ?
S1 C10 . 1.8056(12) ?
O1 C1 . 1.2101(16) ?
N1 C12 . 1.3283(16) ?
N1 C11 . 1.3715(17) ?
C1 C9 . 1.4764(17) ?
C1 C2 . 1.5449(17) ?
O2 C2 . 1.4245(14) ?
O2 H2 . 0.8400 ?
N2 C12 . 1.3166(16) ?
N2 H2A . 0.8800 ?
N2 H2B . 0.8800 ?
C2 C10 . 1.5334(17) ?
C2 C3 . 1.5418(17) ?
O3 C3 . 1.2167(16) ?
C3 C4 . 1.4759(17) ?
O4 C11 . 1.2180(16) ?
C4 C5 . 1.3903(18) ?
C4 C9 . 1.3973(18) ?
C5 C6 . 1.3873(19) ?
C5 H5 . 0.9500 ?
C6 C7 . 1.400(2) ?
C6 H6 . 0.9500 ?
C7 C8 . 1.3922(19) ?
C7 H7 . 0.9500 ?
C8 C9 . 1.3942(18) ?
C8 H8 . 0.9500 ?
C10 C11 . 1.5460(17) ?
C10 H10 . 1.0000 ?
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
O2 H2 O3 1_565 0.84 1.99 2.8225(13) 170.0
N2 H2A N1 3_655 0.88 2.07 2.9372(15) 168.4
N2 H2B O2 2_645 0.88 2.14 2.9629(14) 154.6
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O1 C1 C2 O2 . . . . 64.08(15) ?
C9 C1 C2 O2 . . . . -111.21(11) ?
O1 C1 C2 C10 . . . . -58.41(15) ?
C9 C1 C2 C10 . . . . 126.30(11) ?
O1 C1 C2 C3 . . . . 177.88(11) ?
C9 C1 C2 C3 . . . . 2.59(12) ?
O2 C2 C3 O3 . . . . -63.22(15) ?
C10 C2 C3 O3 . . . . 60.14(16) ?
C1 C2 C3 O3 . . . . -178.97(12) ?
O2 C2 C3 C4 . . . . 113.91(10) ?
C10 C2 C3 C4 . . . . -122.72(11) ?
C1 C2 C3 C4 . . . . -1.84(12) ?
O3 C3 C4 C5 . . . . -1.2(2) ?
C2 C3 C4 C5 . . . . -178.24(12) ?
O3 C3 C4 C9 . . . . 177.42(12) ?
C2 C3 C4 C9 . . . . 0.41(14) ?
C9 C4 C5 C6 . . . . -1.35(18) ?
C3 C4 C5 C6 . . . . 177.19(12) ?
C4 C5 C6 C7 . . . . -0.65(19) ?
C5 C6 C7 C8 . . . . 2.1(2) ?
C6 C7 C8 C9 . . . . -1.44(19) ?
C7 C8 C9 C4 . . . . -0.56(19) ?
C7 C8 C9 C1 . . . . -178.27(12) ?
C5 C4 C9 C8 . . . . 1.99(19) ?
C3 C4 C9 C8 . . . . -176.79(11) ?
C5 C4 C9 C1 . . . . -179.91(11) ?
C3 C4 C9 C1 . . . . 1.32(14) ?
O1 C1 C9 C8 . . . . 0.5(2) ?
C2 C1 C9 C8 . . . . 175.40(12) ?
O1 C1 C9 C4 . . . . -177.45(12) ?
C2 C1 C9 C4 . . . . -2.51(14) ?
O2 C2 C10 C11 . . . . 169.35(10) ?
C3 C2 C10 C11 . . . . 47.95(14) ?
C1 C2 C10 C11 . . . . -68.72(13) ?
O2 C2 C10 S1 . . . . 49.13(12) ?
C3 C2 C10 S1 . . . . -72.27(12) ?
C1 C2 C10 S1 . . . . 171.06(8) ?
C12 S1 C10 C2 . . . . 124.72(9) ?
C12 S1 C10 C11 . . . . 0.93(9) ?
C12 N1 C11 O4 . . . . -176.05(12) ?
C12 N1 C11 C10 . . . . 3.27(15) ?
C2 C10 C11 O4 . . . . 52.60(16) ?
S1 C10 C11 O4 . . . . 176.80(10) ?
C2 C10 C11 N1 . . . . -126.76(11) ?
S1 C10 C11 N1 . . . . -2.56(13) ?
C11 N1 C12 N2 . . . . 178.04(12) ?
C11 N1 C12 S1 . . . . -2.57(14) ?
C10 S1 C12 N2 . . . . -179.74(11) ?
C10 S1 C12 N1 . . . . 0.85(10) ?
