#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/68/2226886.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_2226886
loop_
_publ_author_name
'Yaqub, Muhammad'
'Mahmood, Khalid'
'Tahir, M. Nawaz'
'Shafiq, Zahid'
'Rauf, Abdul'
_publ_section_title
;
 6,7,8,9-Tetrahydro-4b,9b-dihydroxyindano[1,2-b]indoline-9,10-dione
 monohydrate
;
_journal_coeditor_code           HB5521
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1886
_journal_paper_doi               10.1107/S1600536810025328
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C15 H13 N O4, H2 O'
_chemical_formula_moiety         'C15 H13 N O4, H2 O'
_chemical_formula_sum            'C15 H15 N O5'
_chemical_formula_weight         289.28
_chemical_name_systematic
;
6,7,8,9-Tetrahydro-4b,9b-dihydroxyindano[1,2-b]indoline-9,10-dione
monohydrate
;
_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
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   10.703(2)
_cell_length_b                   13.275(4)
_cell_length_c                   19.683(5)
_cell_measurement_reflns_used    1576
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.25
_cell_measurement_theta_min      2.65
_cell_volume                     2796.6(12)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_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_detector_area_resol_mean 8.20
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_diffrn_measurement_method       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  0.0662
_diffrn_reflns_av_sigmaI/netI    0.0447
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            17463
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         2.65
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  0.978
_exptl_absorpt_correction_T_min  0.970
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1216
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.203
_refine_diff_density_min         -0.197
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     206
_refine_ls_number_reflns         2532
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.0911
_refine_ls_R_factor_gt           0.0474
_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)+(0.0498P)²+1.2061P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1056
_refine_ls_wR_factor_ref         0.1349
_reflns_number_gt                1576
_reflns_number_total             2532
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb5521.cif
_cod_data_source_block           I
_cod_database_code               2226886
_cod_database_fobs_code          2226886
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 1/2-x,-y,1/2+z
3 1/2+x,1/2-y,-z
4 -x,1/2+y,1/2-z
5 -x,-y,-z
6 1/2+x,y,1/2-z
7 1/2-x,1/2+y,z
8 x,1/2-y,1/2+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_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
O O1 0.6918(2) -0.15555(15) 0.11236(10) 0.0602(8) Uani . . 1.000
O O2 0.91068(17) -0.08706(14) 0.03362(9) 0.0464(7) Uani . . 1.000
O O3 0.64800(18) -0.14565(14) -0.04188(10) 0.0540(7) Uani . . 1.000
O O4 0.98666(17) 0.09354(16) 0.09227(9) 0.0498(7) Uani . . 1.000
N N1 0.8012(2) 0.15460(17) 0.04090(11) 0.0402(7) Uani . . 1.000
C C1 0.7997(2) 0.0847(2) 0.15639(13) 0.0416(9) Uani . . 1.000
C C2 0.8110(3) 0.1600(2) 0.20487(14) 0.0563(11) Uani . . 1.000
C C3 0.7442(4) 0.1498(3) 0.26471(15) 0.0681(13) Uani . . 1.000
C C4 0.6683(3) 0.0675(3) 0.27637(16) 0.0692(13) Uani . . 1.000
C C5 0.6593(3) -0.0089(3) 0.22942(14) 0.0582(11) Uani . . 1.000
C C6 0.7266(2) 0.0012(2) 0.16905(12) 0.0430(9) Uani . . 1.000
C C7 0.7359(2) -0.07177(19) 0.11328(13) 0.0400(9) Uani . . 1.000
C C8 0.8128(2) -0.02380(18) 0.05584(12) 0.0366(8) Uani . . 1.000
C C9 0.7294(2) 0.00822(18) -0.00174(12) 0.0330(8) Uani . . 1.000
C C10 0.6574(2) -0.0522(2) -0.04613(13) 0.0395(9) Uani . . 1.000
C C11 0.5833(3) 0.0030(2) -0.10052(14) 0.0482(10) Uani . . 1.000
C C12 0.6310(3) 0.1070(2) -0.11767(14) 0.0518(10) Uani . . 1.000
C C13 0.6515(3) 0.16996(19) -0.05470(13) 0.0450(9) Uani . . 1.000
C C14 0.7286(2) 0.11153(18) -0.00559(12) 0.0353(8) Uani . . 1.000
C C15 0.8580(2) 0.08050(19) 0.08678(12) 0.0382(8) Uani . . 1.000
O O5 0.4998(3) 0.2705(2) 0.12020(14) 0.0943(11) Uani . . 1.000
H H1 0.808(2) 0.220(2) 0.0473(13) 0.0483 Uiso . . 1.000
H H2 0.86192 0.21568 0.19739 0.0676 Uiso . . 1.000
H H2A 0.932(3) -0.129(2) 0.0658(15) 0.0556 Uiso . . 1.000
H H3 0.75062 0.19956 0.29781 0.0817 Uiso . . 1.000
H H4 0.62257 0.06369 0.31648 0.0830 Uiso . . 1.000
H H4A 1.018(3) 0.085(2) 0.0537(15) 0.0597 Uiso . . 1.000
H H5 0.61011 -0.06532 0.23762 0.0701 Uiso . . 1.000
H H11A 0.58359 -0.03738 -0.14158 0.0578 Uiso . . 1.000
H H11B 0.49724 0.00876 -0.08548 0.0578 Uiso . . 1.000
H H12A 0.57126 0.14056 -0.14700 0.0621 Uiso . . 1.000
H H12B 0.70914 0.10108 -0.14231 0.0621 Uiso . . 1.000
H H13A 0.69391 0.23208 -0.06659 0.0540 Uiso . . 1.000
H H13B 0.57173 0.18695 -0.03431 0.0540 Uiso . . 1.000
H H51 0.452(3) 0.224(2) 0.0954(17) 0.1131 Uiso . . 1.000
H H52 0.526(4) 0.239(3) 0.1564(14) 0.1131 Uiso . . 1.000
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_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C8 O2 H2A . . . 110(2) no
C15 O4 H4A . . . 108(2) no
H51 O5 H52 . . . 107(3) no
C14 N1 C15 . . . 112.2(2) no
C15 N1 H1 . . . 122.6(16) no
C14 N1 H1 . . . 124.8(16) no
C2 C1 C6 . . . 120.3(2) no
C2 C1 C15 . . . 128.0(2) no
C6 C1 C15 . . . 111.7(2) no
C1 C2 C3 . . . 118.0(3) no
C2 C3 C4 . . . 121.5(3) no
C3 C4 C5 . . . 120.9(3) no
C4 C5 C6 . . . 117.7(3) no
C5 C6 C7 . . . 127.5(3) no
C1 C6 C5 . . . 121.6(3) no
C1 C6 C7 . . . 110.9(2) no
C6 C7 C8 . . . 108.3(2) no
O1 C7 C6 . . . 126.3(2) no
O1 C7 C8 . . . 125.4(2) no
O2 C8 C9 . . . 112.03(19) no
O2 C8 C7 . . . 112.26(19) no
C7 C8 C9 . . . 110.71(18) no
C7 C8 C15 . . . 104.02(19) no
C9 C8 C15 . . . 102.91(19) no
O2 C8 C15 . . . 114.29(18) no
C8 C9 C14 . . . 109.1(2) no
C10 C9 C14 . . . 121.9(2) no
C8 C9 C10 . . . 129.0(2) no
O3 C10 C9 . . . 124.5(2) no
O3 C10 C11 . . . 119.0(2) no
C9 C10 C11 . . . 116.5(2) no
C10 C11 C12 . . . 114.9(2) no
C11 C12 C13 . . . 111.8(2) no
C12 C13 C14 . . . 109.0(2) no
N1 C14 C13 . . . 123.1(2) no
N1 C14 C9 . . . 112.8(2) no
C9 C14 C13 . . . 124.0(2) no
N1 C15 C8 . . . 102.84(18) no
C1 C15 C8 . . . 104.77(19) no
O4 C15 N1 . . . 112.0(2) no
O4 C15 C1 . . . 109.54(19) no
N1 C15 C1 . . . 111.31(19) no
O4 C15 C8 . . . 116.07(19) no
C1 C2 H2 . . . 121.00 no
C3 C2 H2 . . . 121.00 no
C4 C3 H3 . . . 119.00 no
C2 C3 H3 . . . 119.00 no
C3 C4 H4 . . . 120.00 no
C5 C4 H4 . . . 120.00 no
C4 C5 H5 . . . 121.00 no
C6 C5 H5 . . . 121.00 no
C10 C11 H11B . . . 109.00 no
C12 C11 H11A . . . 109.00 no
C12 C11 H11B . . . 108.00 no
H11A C11 H11B . . . 108.00 no
C10 C11 H11A . . . 109.00 no
C11 C12 H12B . . . 109.00 no
C13 C12 H12A . . . 109.00 no
C11 C12 H12A . . . 109.00 no
H12A C12 H12B . . . 108.00 no
C13 C12 H12B . . . 109.00 no
C12 C13 H13A . . . 110.00 no
C12 C13 H13B . . . 110.00 no
C14 C13 H13B . . . 110.00 no
H13A C13 H13B . . . 108.00 no
C14 C13 H13A . . . 110.00 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C7 . . 1.208(3) no
O2 C8 . . 1.412(3) no
O3 C10 . . 1.247(3) no
O4 C15 . . 1.392(3) no
O2 H2A . . 0.87(3) no
O4 H4A . . 0.84(3) no
O5 H51 . . 0.94(3) no
O5 H52 . . 0.87(3) no
N1 C14 . . 1.330(3) no
N1 C15 . . 1.467(3) no
N1 H1 . . 0.88(3) no
C1 C6 . . 1.380(4) no
C1 C2 . . 1.387(4) no
C1 C15 . . 1.507(3) no
C2 C3 . . 1.385(4) no
C3 C4 . . 1.381(6) no
C4 C5 . . 1.376(5) no
C5 C6 . . 1.396(4) no
C6 C7 . . 1.467(4) no
C7 C8 . . 1.537(3) no
C8 C9 . . 1.504(3) no
C8 C15 . . 1.588(3) no
C9 C14 . . 1.374(3) no
C9 C10 . . 1.414(3) no
C10 C11 . . 1.521(4) no
C11 C12 . . 1.510(4) no
C12 C13 . . 1.511(4) no
C13 C14 . . 1.489(4) no
C2 H2 . . 0.9300 no
C3 H3 . . 0.9300 no
C4 H4 . . 0.9300 no
C5 H5 . . 0.9300 no
C11 H11B . . 0.9700 no
C11 H11A . . 0.9700 no
C12 H12A . . 0.9700 no
C12 H12B . . 0.9700 no
C13 H13B . . 0.9700 no
C13 H13A . . 0.9700 no
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
N1 H1 O1 7_655 0.88(3) 2.09(3) 2.887(3) 150(2) yes
N1 H1 O3 7_655 0.88(3) 2.55(3) 3.159(3) 127(2) yes
O2 H2A O5 7_645 0.87(3) 1.86(3) 2.720(3) 168(3) yes
O4 H4A O2 5_755 0.84(3) 1.88(3) 2.712(3) 171(3) yes
O5 H51 O3 5_655 0.94(3) 1.83(3) 2.762(4) 174(3) yes
C2 H2 O1 7_655 0.93 2.46 3.052(3) 122 yes
C4 H4 O4 6_455 0.93 2.34 3.253(4) 165 yes
C13 H13A O3 7_655 0.97 2.39 3.265(4) 149 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
C15 N1 C14 C9 . . . . -3.2(3) no
C15 N1 C14 C13 . . . . 174.7(2) no
C14 N1 C15 O4 . . . . 129.3(2) no
C14 N1 C15 C1 . . . . -107.7(2) no
C14 N1 C15 C8 . . . . 4.0(2) no
C6 C1 C2 C3 . . . . -1.9(4) no
C15 C1 C2 C3 . . . . 177.3(3) no
C2 C1 C6 C5 . . . . 2.0(4) no
C2 C1 C6 C7 . . . . -175.7(2) no
C15 C1 C6 C5 . . . . -177.3(2) no
C15 C1 C6 C7 . . . . 5.1(3) no
C2 C1 C15 O4 . . . . 54.1(3) no
C2 C1 C15 N1 . . . . -70.3(3) no
C2 C1 C15 C8 . . . . 179.3(2) no
C6 C1 C15 O4 . . . . -126.7(2) no
C6 C1 C15 N1 . . . . 108.9(2) no
C6 C1 C15 C8 . . . . -1.5(3) no
C1 C2 C3 C4 . . . . 0.0(5) no
C2 C3 C4 C5 . . . . 1.9(6) no
C3 C4 C5 C6 . . . . -1.8(5) no
C4 C5 C6 C1 . . . . -0.1(4) no
C4 C5 C6 C7 . . . . 177.1(3) no
C1 C6 C7 O1 . . . . 173.0(2) no
C1 C6 C7 C8 . . . . -6.5(3) no
C5 C6 C7 O1 . . . . -4.4(4) no
C5 C6 C7 C8 . . . . 176.1(3) no
O1 C7 C8 O2 . . . . -50.3(3) no
O1 C7 C8 C9 . . . . 75.7(3) no
O1 C7 C8 C15 . . . . -174.4(2) no
C6 C7 C8 O2 . . . . 129.2(2) no
C6 C7 C8 C9 . . . . -104.8(2) no
C6 C7 C8 C15 . . . . 5.2(2) no
O2 C8 C9 C10 . . . . 60.0(3) no
O2 C8 C9 C14 . . . . -121.6(2) no
C7 C8 C9 C10 . . . . -66.1(3) no
C7 C8 C9 C14 . . . . 112.3(2) no
C15 C8 C9 C10 . . . . -176.7(2) no
C15 C8 C9 C14 . . . . 1.7(2) no
O2 C8 C15 O4 . . . . -4.1(3) no
O2 C8 C15 N1 . . . . 118.5(2) no
O2 C8 C15 C1 . . . . -125.1(2) no
C7 C8 C15 O4 . . . . 118.6(2) no
C7 C8 C15 N1 . . . . -118.75(19) no
C7 C8 C15 C1 . . . . -2.3(2) no
C9 C8 C15 O4 . . . . -125.8(2) no
C9 C8 C15 N1 . . . . -3.2(2) no
C9 C8 C15 C1 . . . . 113.25(19) no
C8 C9 C10 O3 . . . . 3.4(4) no
C8 C9 C10 C11 . . . . -179.2(2) no
C14 C9 C10 O3 . . . . -174.8(2) no
C14 C9 C10 C11 . . . . 2.6(3) no
C8 C9 C14 N1 . . . . 0.8(3) no
C8 C9 C14 C13 . . . . -177.1(2) no
C10 C9 C14 N1 . . . . 179.3(2) no
C10 C9 C14 C13 . . . . 1.4(4) no
O3 C10 C11 C12 . . . . -160.4(2) no
C9 C10 C11 C12 . . . . 22.0(3) no
C10 C11 C12 C13 . . . . -49.8(3) no
C11 C12 C13 C14 . . . . 50.8(3) no
C12 C13 C14 N1 . . . . 153.7(2) no
C12 C13 C14 C9 . . . . -28.7(3) no
