#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/03/2230378.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_2230378
loop_
_publ_author_name
'Ghalib, Raza Murad'
'Hashim, Rokiah'
'Mehdi, Sayed Hasan'
'Quah, Ching Kheng'
'Fun, Hoong-Kun'
_publ_section_title
;
 3a,8a-Dihydroxy-1,3,3a,8a-tetrahydroindeno[1,2-d]imidazole-2,8-dione
;
_journal_coeditor_code           IS2712
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1525
_journal_paper_doi               10.1107/S1600536811019039
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C10 H8 N2 O4'
_chemical_formula_moiety         'C10 H8 N2 O4'
_chemical_formula_sum            'C10 H8 N2 O4'
_chemical_formula_weight         220.18
_chemical_name_systematic
;
3a,8a-Dihydroxy-1,3,3a,8a-tetrahydroindeno[1,2-d]imidazole-2,8-dione
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                94.2580(10)
_cell_angle_beta                 102.7730(10)
_cell_angle_gamma                93.7250(10)
_cell_formula_units_Z            2
_cell_length_a                   6.7914(2)
_cell_length_b                   7.3201(2)
_cell_length_c                   9.5006(3)
_cell_measurement_reflns_used    2749
_cell_measurement_temperature    296
_cell_measurement_theta_max      27.55
_cell_measurement_theta_min      3.09
_cell_volume                     457.74(2)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
'SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      296
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type
;
Bruker SMART APEXII CCD area-detector
;
_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  0.0224
_diffrn_reflns_av_sigmaI/netI    0.0260
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6684
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.21
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.126
_exptl_absorpt_correction_T_max  0.9938
_exptl_absorpt_correction_T_min  0.9523
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.598
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             228
_exptl_crystal_size_max          0.391
_exptl_crystal_size_mid          0.153
_exptl_crystal_size_min          0.049
_refine_diff_density_max         0.245
_refine_diff_density_min         -0.227
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     177
_refine_ls_number_reflns         2081
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0559
_refine_ls_R_factor_gt           0.0395
_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)+(0.0511P)²+0.1396P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0982
_refine_ls_wR_factor_ref         0.1095
_reflns_number_gt                1634
_reflns_number_total             2081
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            is2712.cif
_cod_data_source_block           I
_cod_database_code               2230378
_cod_database_fobs_code          2230378
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 1.26218(17) 0.50614(16) 0.93570(12) 0.0382(3) Uani d . 1 1 . .
O O2 0.73914(19) 0.13075(18) 0.94567(13) 0.0394(3) Uani d . 1 1 . .
O O3 0.59082(18) 0.39814(17) 0.75936(14) 0.0376(3) Uani d . 1 1 . .
O O4 0.8536(2) -0.15340(16) 0.77260(14) 0.0464(4) Uani d . 1 1 . .
N N1 0.9431(2) 0.46753(19) 0.78463(15) 0.0345(3) Uani d . 1 1 . .
N N2 1.0569(2) 0.23428(18) 0.90164(15) 0.0323(3) Uani d . 1 1 . .
C C1 1.1014(2) 0.4122(2) 0.87930(16) 0.0294(3) Uani d . 1 1 . .
C C2 0.7722(2) 0.3301(2) 0.74365(16) 0.0284(3) Uani d . 1 1 . .
C C3 0.7435(2) 0.2416(2) 0.59059(16) 0.0279(3) Uani d . 1 1 . .
C C4 0.6895(3) 0.3254(3) 0.46259(18) 0.0371(4) Uani d . 1 1 . .
C C5 0.6634(3) 0.2169(3) 0.33296(19) 0.0431(5) Uani d . 1 1 . .
C C6 0.6904(3) 0.0303(3) 0.32948(19) 0.0424(4) Uani d . 1 1 . .
C C7 0.7470(3) -0.0527(2) 0.45616(18) 0.0358(4) Uani d . 1 1 . .
C C8 0.7735(2) 0.0553(2) 0.58705(17) 0.0290(3) Uani d . 1 1 . .
C C9 0.8272(2) -0.0003(2) 0.73466(17) 0.0303(4) Uani d . 1 1 . .
C C10 0.8466(2) 0.1716(2) 0.84121(16) 0.0286(3) Uani d . 1 1 . .
H H4A 0.672(3) 0.461(3) 0.467(2) 0.048(5) Uiso d . 1 1 . .
H H5A 0.617(3) 0.274(3) 0.245(2) 0.056(6) Uiso d . 1 1 . .
H H6A 0.670(3) -0.043(3) 0.237(2) 0.059(6) Uiso d . 1 1 . .
H H7A 0.764(3) -0.183(3) 0.455(2) 0.048(6) Uiso d . 1 1 . .
H H1O3 0.605(4) 0.440(3) 0.852(3) 0.070(7) Uiso d . 1 1 . .
H H1O2 0.735(4) 0.242(4) 1.002(3) 0.089(9) Uiso d . 1 1 . .
H H1N2 1.128(3) 0.188(3) 0.970(2) 0.041(5) Uiso d . 1 1 . .
H H1N1 0.935(3) 0.580(3) 0.765(2) 0.049(6) Uiso d . 1 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'
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
C10 O2 H1O2 . . 107.1(16) ?
C2 O3 H1O3 . . 108.0(16) ?
C1 N1 C2 . . 113.31(13) ?
C1 N1 H1N1 . . 122.8(14) ?
C2 N1 H1N1 . . 122.7(14) ?
C1 N2 C10 . . 112.65(13) ?
C1 N2 H1N2 . . 119.6(13) ?
C10 N2 H1N2 . . 122.8(13) ?
O1 C1 N1 . . 126.05(15) ?
O1 C1 N2 . . 125.48(15) ?
N1 C1 N2 . . 108.47(14) ?
O3 C2 N1 . . 112.93(13) ?
O3 C2 C3 . . 108.64(12) ?
N1 C2 C3 . . 113.22(13) ?
O3 C2 C10 . . 115.83(12) ?
N1 C2 C10 . . 102.17(12) ?
C3 C2 C10 . . 103.71(12) ?
C4 C3 C8 . . 120.46(15) ?
C4 C3 C2 . . 127.23(15) ?
C8 C3 C2 . . 112.30(13) ?
C5 C4 C3 . . 117.90(17) ?
C5 C4 H4A . . 122.5(11) ?
C3 C4 H4A . . 119.6(11) ?
C4 C5 C6 . . 121.62(16) ?
C4 C5 H5A . . 117.3(13) ?
C6 C5 H5A . . 120.9(13) ?
C7 C6 C5 . . 120.68(17) ?
C7 C6 H6A . . 119.2(13) ?
C5 C6 H6A . . 120.1(13) ?
C6 C7 C8 . . 118.12(17) ?
C6 C7 H7A . . 121.2(12) ?
C8 C7 H7A . . 120.6(12) ?
C3 C8 C7 . . 121.22(15) ?
C3 C8 C9 . . 110.13(14) ?
C7 C8 C9 . . 128.63(15) ?
O4 C9 C8 . . 128.27(15) ?
O4 C9 C10 . . 123.41(14) ?
C8 C9 C10 . . 108.32(12) ?
O2 C10 N2 . . 113.44(12) ?
O2 C10 C9 . . 107.94(12) ?
N2 C10 C9 . . 111.16(13) ?
O2 C10 C2 . . 116.95(13) ?
N2 C10 C2 . . 102.00(11) ?
C9 C10 C2 . . 104.99(12) ?
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
O1 C1 . 1.2415(18) ?
O2 C10 . 1.3939(19) ?
O2 H1O2 . 0.94(3) ?
O3 C2 . 1.392(2) ?
O3 H1O3 . 0.89(3) ?
O4 C9 . 1.2145(18) ?
N1 C1 . 1.346(2) ?
N1 C2 . 1.4496(19) ?
N1 H1N1 . 0.86(2) ?
N2 C1 . 1.360(2) ?
N2 C10 . 1.447(2) ?
N2 H1N2 . 0.83(2) ?
C2 C3 . 1.513(2) ?
C2 C10 . 1.578(2) ?
C3 C4 . 1.390(2) ?
C3 C8 . 1.391(2) ?
C4 C5 . 1.385(3) ?
C4 H4A . 1.01(2) ?
C5 C6 . 1.388(3) ?
C5 H5A . 0.96(2) ?
C6 C7 . 1.378(3) ?
C6 H6A . 0.97(2) ?
C7 C8 . 1.393(2) ?
C7 H7A . 0.96(2) ?
C8 C9 . 1.464(2) ?
C9 C10 . 1.535(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
_geom_hbond_publ_flag
O3 H1O3 O1 2_767 0.89(3) 2.02(3) 2.8653(17) 158(2) yes
O2 H1O2 O1 2_767 0.95(3) 1.89(3) 2.8103(17) 163(2) yes
N2 H1N2 O4 2_757 0.83(2) 2.454(19) 3.1282(19) 139.3(18) yes
N1 H1N1 O4 1_565 0.86(2) 2.06(2) 2.8841(18) 159.4(19) 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
C2 N1 C1 O1 . . . . -176.86(15) ?
C2 N1 C1 N2 . . . . 3.96(19) ?
C10 N2 C1 O1 . . . . 170.05(15) ?
C10 N2 C1 N1 . . . . -10.77(19) ?
C1 N1 C2 O3 . . . . 128.62(15) ?
C1 N1 C2 C3 . . . . -107.37(15) ?
C1 N1 C2 C10 . . . . 3.51(18) ?
O3 C2 C3 C4 . . . . 60.0(2) ?
N1 C2 C3 C4 . . . . -66.3(2) ?
C10 C2 C3 C4 . . . . -176.23(15) ?
O3 C2 C3 C8 . . . . -118.71(14) ?
N1 C2 C3 C8 . . . . 114.97(15) ?
C10 C2 C3 C8 . . . . 5.04(17) ?
C8 C3 C4 C5 . . . . 1.1(2) ?
C2 C3 C4 C5 . . . . -177.49(16) ?
C3 C4 C5 C6 . . . . -0.2(3) ?
C4 C5 C6 C7 . . . . -0.8(3) ?
C5 C6 C7 C8 . . . . 0.8(3) ?
C4 C3 C8 C7 . . . . -1.2(2) ?
C2 C3 C8 C7 . . . . 177.66(14) ?
C4 C3 C8 C9 . . . . -179.53(14) ?
C2 C3 C8 C9 . . . . -0.71(18) ?
C6 C7 C8 C3 . . . . 0.2(2) ?
C6 C7 C8 C9 . . . . 178.21(15) ?
C3 C8 C9 O4 . . . . 175.78(16) ?
C7 C8 C9 O4 . . . . -2.4(3) ?
C3 C8 C9 C10 . . . . -4.17(17) ?
C7 C8 C9 C10 . . . . 177.62(15) ?
C1 N2 C10 O2 . . . . -114.40(15) ?
C1 N2 C10 C9 . . . . 123.74(14) ?
C1 N2 C10 C2 . . . . 12.28(17) ?
O4 C9 C10 O2 . . . . -47.5(2) ?
C8 C9 C10 O2 . . . . 132.48(13) ?
O4 C9 C10 N2 . . . . 77.5(2) ?
C8 C9 C10 N2 . . . . -102.51(14) ?
O4 C9 C10 C2 . . . . -172.92(15) ?
C8 C9 C10 C2 . . . . 7.03(16) ?
O3 C2 C10 O2 . . . . -7.76(19) ?
N1 C2 C10 O2 . . . . 115.42(14) ?
C3 C2 C10 O2 . . . . -126.69(13) ?
O3 C2 C10 N2 . . . . -132.12(13) ?
N1 C2 C10 N2 . . . . -8.94(15) ?
C3 C2 C10 N2 . . . . 108.95(13) ?
O3 C2 C10 C9 . . . . 111.83(14) ?
N1 C2 C10 C9 . . . . -124.99(13) ?
C3 C2 C10 C9 . . . . -7.09(15) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 326795
