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#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/74/2227458.cif $
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#
# 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_2227458
loop_
_publ_author_name
'Sundar, J. Kalyana'
'Maharani, S.'
'Kumar, R. Ranjith'
'Natarajan, S.'
'Suresh, J.'
'Lakshman, P. L. Nilantha'
_publ_section_title
;
 rac-2-Hydroxy-2-(2-oxocyclopentyl)-1H-indene-1,3(2H)-dione
;
_journal_coeditor_code           GK2301
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2967
_journal_paper_doi               10.1107/S1600536810042856
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C14 H12 O4'
_chemical_formula_moiety         'C14 H12 O4'
_chemical_formula_sum            'C14 H12 O4'
_chemical_formula_weight         244.24
_chemical_name_systematic
;
rac-2-Hydroxy-2-(2-oxocyclopentyl)-1H-indene-1,3(2H)-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                66.95(3)
_cell_angle_beta                 74.36(2)
_cell_angle_gamma                68.50(3)
_cell_formula_units_Z            2
_cell_length_a                   8.044(3)
_cell_length_b                   8.404(4)
_cell_length_c                   10.239(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      2
_cell_volume                     586.1(4)
_computing_cell_refinement       'CAD-4 EXPRESS (Enraf--Nonius, 1994)'
_computing_data_collection       'CAD-4 EXPRESS (Enraf--Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1996)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Nonius MACH3'
_diffrn_measurement_method       ω-2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0161
_diffrn_reflns_av_sigmaI/netI    0.0106
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            2534
_diffrn_reflns_theta_full        24.97
_diffrn_reflns_theta_max         24.97
_diffrn_reflns_theta_min         2.19
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  0.9810
_exptl_absorpt_correction_T_min  0.9740
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             256
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.234
_refine_ls_extinction_coef       0.059(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2054
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0405
_refine_ls_R_factor_gt           0.0376
_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)+(0.0487P)²+0.2034P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1015
_refine_ls_wR_factor_ref         0.1040
_reflns_number_gt                1886
_reflns_number_total             2054
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            gk2301.cif
_cod_data_source_block           I
_cod_database_code               2227458
_cod_database_fobs_code          2227458
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_disorder_assembly
_atom_site_disorder_group
C C1 0.4901(2) 0.0143(2) 0.33717(14) 0.0367(4) Uani d . 1 . .
C C2 0.6584(2) -0.1372(2) 0.32374(19) 0.0505(4) Uani d . 1 . .
H H2A 0.7411 -0.1548 0.3852 0.061 Uiso calc R 1 . .
H H2B 0.7191 -0.1129 0.2254 0.061 Uiso calc R 1 . .
C C3 0.5929(3) -0.3013(2) 0.3708(2) 0.0551(5) Uani d . 1 . .
H H3A 0.5821 -0.3580 0.4742 0.066 Uiso calc R 1 . .
H H3B 0.6745 -0.3896 0.3258 0.066 Uiso calc R 1 . .
C C4 0.4084(2) -0.2245(2) 0.3207(2) 0.0494(4) Uani d . 1 . .
H H4A 0.3353 -0.3064 0.3719 0.059 Uiso calc R 1 . .
H H4B 0.4206 -0.2008 0.2184 0.059 Uiso calc R 1 . .
C C5 0.3268(2) -0.04868(19) 0.35711(15) 0.0367(4) Uani d . 1 . .
H H5 0.2797 -0.0818 0.4598 0.044 Uiso calc R 1 . .
C C6 0.17097(19) 0.09543(19) 0.27852(15) 0.0353(3) Uani d . 1 . .
C C7 0.2311(2) 0.1817(2) 0.11679(15) 0.0387(4) Uani d . 1 . .
C C8 0.2136(2) 0.3728(2) 0.09029(16) 0.0379(4) Uani d . 1 . .
C C9 0.2631(2) 0.5004(2) -0.03520(18) 0.0502(4) Uani d . 1 . .
H H9 0.3169 0.4710 -0.1186 0.060 Uiso calc R 1 . .
C C10 0.2304(3) 0.6721(2) -0.0329(2) 0.0573(5) Uani d . 1 . .
H H10 0.2618 0.7600 -0.1163 0.069 Uiso calc R 1 . .
C C11 0.1513(3) 0.7168(2) 0.0916(2) 0.0561(5) Uani d . 1 . .
H H11 0.1308 0.8338 0.0902 0.067 Uiso calc R 1 . .
C C12 0.1028(2) 0.5900(2) 0.21723(19) 0.0470(4) Uani d . 1 . .
H H12 0.0508 0.6193 0.3008 0.056 Uiso calc R 1 . .
C C13 0.13396(19) 0.4179(2) 0.21488(16) 0.0366(3) Uani d . 1 . .
C C14 0.09696(19) 0.2590(2) 0.33215(15) 0.0362(3) Uani d . 1 . .
O O1 0.48152(16) 0.16243(15) 0.33474(12) 0.0484(3) Uani d . 1 . .
O O2 0.03172(15) 0.02227(15) 0.29221(13) 0.0487(3) Uani d . 1 . .
H H2 -0.0080 -0.0170 0.3773 0.073 Uiso calc R 1 . .
O O3 0.2801(2) 0.10548(17) 0.02872(13) 0.0602(4) Uani d . 1 . .
O O4 0.01604(16) 0.25544(16) 0.45179(12) 0.0502(3) 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'
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
O1 C1 C2 . . 126.74(15) ?
O1 C1 C5 . . 124.60(14) ?
C2 C1 C5 . . 108.66(13) ?
C1 C2 C3 . . 104.51(14) ?
C1 C2 H2A . . 110.9 ?
C3 C2 H2A . . 110.9 ?
C1 C2 H2B . . 110.9 ?
C3 C2 H2B . . 110.9 ?
H2A C2 H2B . . 108.9 ?
C2 C3 C4 . . 103.75(14) ?
C2 C3 H3A . . 111.0 ?
C4 C3 H3A . . 111.0 ?
C2 C3 H3B . . 111.0 ?
C4 C3 H3B . . 111.0 ?
H3A C3 H3B . . 109.0 ?
C3 C4 C5 . . 102.74(13) ?
C3 C4 H4A . . 111.2 ?
C5 C4 H4A . . 111.2 ?
C3 C4 H4B . . 111.2 ?
C5 C4 H4B . . 111.2 ?
H4A C4 H4B . . 109.1 ?
C1 C5 C4 . . 103.78(13) ?
C1 C5 C6 . . 114.77(12) ?
C4 C5 C6 . . 117.09(13) ?
C1 C5 H5 . . 106.9 ?
C4 C5 H5 . . 106.9 ?
C6 C5 H5 . . 106.9 ?
O2 C6 C5 . . 111.26(12) ?
O2 C6 C14 . . 110.92(12) ?
C5 C6 C14 . . 110.99(12) ?
O2 C6 C7 . . 107.82(12) ?
C5 C6 C7 . . 113.02(12) ?
C14 C6 C7 . . 102.49(12) ?
O3 C7 C8 . . 126.80(14) ?
O3 C7 C6 . . 125.30(14) ?
C8 C7 C6 . . 107.89(13) ?
C9 C8 C13 . . 120.56(15) ?
C9 C8 C7 . . 129.09(15) ?
C13 C8 C7 . . 110.35(13) ?
C10 C9 C8 . . 118.04(17) ?
C10 C9 H9 . . 121.0 ?
C8 C9 H9 . . 121.0 ?
C9 C10 C11 . . 121.33(16) ?
C9 C10 H10 . . 119.3 ?
C11 C10 H10 . . 119.3 ?
C12 C11 C10 . . 120.90(17) ?
C12 C11 H11 . . 119.6 ?
C10 C11 H11 . . 119.6 ?
C11 C12 C13 . . 117.90(17) ?
C11 C12 H12 . . 121.1 ?
C13 C12 H12 . . 121.1 ?
C12 C13 C8 . . 121.28(14) ?
C12 C13 C14 . . 129.02(15) ?
C8 C13 C14 . . 109.69(14) ?
O4 C14 C13 . . 126.49(15) ?
O4 C14 C6 . . 124.45(13) ?
C13 C14 C6 . . 109.03(12) ?
C6 O2 H2 . . 109.5 ?
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
C1 O1 . 1.2116(19) ?
C1 C2 . 1.499(2) ?
C1 C5 . 1.526(2) ?
C2 C3 . 1.512(3) ?
C2 H2A . 0.9700 ?
C2 H2B . 0.9700 ?
C3 C4 . 1.528(3) ?
C3 H3A . 0.9700 ?
C3 H3B . 0.9700 ?
C4 C5 . 1.531(2) ?
C4 H4A . 0.9700 ?
C4 H4B . 0.9700 ?
C5 C6 . 1.534(2) ?
C5 H5 . 0.9800 ?
C6 O2 . 1.4160(18) ?
C6 C14 . 1.536(2) ?
C6 C7 . 1.545(2) ?
C7 O3 . 1.2059(19) ?
C7 C8 . 1.479(2) ?
C8 C9 . 1.384(2) ?
C8 C13 . 1.393(2) ?
C9 C10 . 1.378(3) ?
C9 H9 . 0.9300 ?
C10 C11 . 1.391(3) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.379(3) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.383(2) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.469(2) ?
C14 O4 . 1.2169(18) ?
O2 H2 . 0.8200 ?
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
O2 H2 O4 2_556 0.82 2.09 2.791(2) 143 y
C2 H2A O4 2_656 0.97 2.60 3.560(2) 171 n
C2 H2B O3 2_655 0.97 2.58 3.423(2) 146 n
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 C3 . . . . 166.12(15) ?
C5 C1 C2 C3 . . . . -13.03(17) ?
C1 C2 C3 C4 . . . . 33.50(18) ?
C2 C3 C4 C5 . . . . -41.27(18) ?
O1 C1 C5 C4 . . . . 168.45(14) ?
C2 C1 C5 C4 . . . . -12.37(16) ?
O1 C1 C5 C6 . . . . 39.4(2) ?
C2 C1 C5 C6 . . . . -141.39(14) ?
C3 C4 C5 C1 . . . . 32.54(16) ?
C3 C4 C5 C6 . . . . 160.13(14) ?
C1 C5 C6 O2 . . . . 174.96(11) ?
C4 C5 C6 O2 . . . . 52.92(18) ?
C1 C5 C6 C14 . . . . -61.01(16) ?
C4 C5 C6 C14 . . . . 176.94(12) ?
C1 C5 C6 C7 . . . . 53.49(17) ?
C4 C5 C6 C7 . . . . -68.56(17) ?
O2 C6 C7 O3 . . . . -54.4(2) ?
C5 C6 C7 O3 . . . . 69.0(2) ?
C14 C6 C7 O3 . . . . -171.52(16) ?
O2 C6 C7 C8 . . . . 124.29(13) ?
C5 C6 C7 C8 . . . . -112.31(14) ?
C14 C6 C7 C8 . . . . 7.21(15) ?
O3 C7 C8 C9 . . . . -6.3(3) ?
C6 C7 C8 C9 . . . . 174.99(15) ?
O3 C7 C8 C13 . . . . 173.24(16) ?
C6 C7 C8 C13 . . . . -5.46(17) ?
C13 C8 C9 C10 . . . . -0.3(2) ?
C7 C8 C9 C10 . . . . 179.19(16) ?
C8 C9 C10 C11 . . . . 0.5(3) ?
C9 C10 C11 C12 . . . . -0.1(3) ?
C10 C11 C12 C13 . . . . -0.5(3) ?
C11 C12 C13 C8 . . . . 0.7(2) ?
C11 C12 C13 C14 . . . . 179.53(15) ?
C9 C8 C13 C12 . . . . -0.3(2) ?
C7 C8 C13 C12 . . . . -179.90(14) ?
C9 C8 C13 C14 . . . . -179.32(14) ?
C7 C8 C13 C14 . . . . 1.09(17) ?
C12 C13 C14 O4 . . . . 7.0(3) ?
C8 C13 C14 O4 . . . . -174.07(15) ?
C12 C13 C14 C6 . . . . -175.15(15) ?
C8 C13 C14 C6 . . . . 3.77(16) ?
O2 C6 C14 O4 . . . . 56.38(19) ?
C5 C6 C14 O4 . . . . -67.85(19) ?
C7 C6 C14 O4 . . . . 171.22(14) ?
O2 C6 C14 C13 . . . . -121.51(13) ?
C5 C6 C14 C13 . . . . 114.26(13) ?
C7 C6 C14 C13 . . . . -6.67(15) ?
