#------------------------------------------------------------------------------
#$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2007332.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_2007332
loop_
_publ_author_name
'Thompson, H. W.'
'Brunskill, A. P. J.'
'Lalancette, R. A.'
_publ_section_title
;
 (+-)-3-Indanone-1-acetic Acid: Heterochiral Catemeric Hydrogen Bonding
 in a \d-Keto Acid
;
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              829
_journal_page_last               831
_journal_volume                  54
_journal_year                    1998
_chemical_formula_analytical     'C11 H10 O3'
_chemical_formula_moiety         'C11 H10 O3'
_chemical_formula_structural     'C11 H10 O3'
_chemical_formula_sum            'C11 H10 O3'
_chemical_formula_weight         190.19
_chemical_melting_point          426
_chemical_name_common            '(+\-)-3-indanone-1-acetic acid'
_chemical_name_systematic
;
(+\-)-2,3-dihydro-3-oxo-1H-indeneacetic Acid
;
_space_group_IT_number           29
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_audit_creation_method           SHELXTL/PC
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.140(2)
_cell_length_b                   9.1670(10)
_cell_length_c                   7.2630(10)
_cell_measurement_reflns_used    37
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      17.76
_cell_measurement_theta_min      5.30
_cell_volume                     941.4(2)
_computing_cell_refinement       XSCANS
_computing_data_collection       'XSCANS (Siemens, 1991)'
_computing_data_reduction        XSCANS
_computing_molecular_graphics    SHELXTL/PC
_computing_publication_material  SHELXTL/PC
_computing_structure_refinement  SHELXTL/PC
_computing_structure_solution    'SHELXTL/PC (Sheldrick, 1994)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       'Siemens P4'
_diffrn_measurement_method       2\q/\q
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.016
_diffrn_reflns_av_sigmaI/netI    0.033
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            2688
_diffrn_reflns_theta_max         29.00
_diffrn_reflns_theta_min         2.22
_diffrn_standards_decay_%        -0.63
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  0.971
_exptl_absorpt_correction_T_min  0.943
_exptl_absorpt_correction_type   'face-indexed numerical (Sheldrick, 1994)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_density_meas      1.350(10)
_exptl_crystal_density_method    'flotation in CCl~4~--toluene'
_exptl_crystal_description
'Rectangular prism singly capped with a rectangular prismoid'
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.70
_exptl_crystal_size_mid          0.60
_exptl_crystal_size_min          0.32
_refine_diff_density_max         0.27
_refine_diff_density_min         -0.15
_refine_ls_abs_structure_details 'Flack (1983)'
_refine_ls_abs_structure_Flack   0.5(16)
_refine_ls_extinction_method     'none (refined to zero)'
_refine_ls_goodness_of_fit_all   1.05
_refine_ls_goodness_of_fit_obs   1.10
_refine_ls_hydrogen_treatment    'H atoms: see below'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     140
_refine_ls_number_reflns         2493
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.05
_refine_ls_restrained_S_obs      1.10
_refine_ls_R_factor_all          0.070
_refine_ls_R_factor_obs          0.050
_refine_ls_shift/esd_max         0.00
_refine_ls_shift/esd_mean        0.00
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme
'calc w = 1/[\s^2^(Fo^2^)+(0.0598P)^2^+0.1029P] where P = (Fo^2^+2Fc^2^)/3'
_refine_ls_wR_factor_all         0.129
_refine_ls_wR_factor_obs         0.117
_reflns_number_observed          1900
_reflns_number_total             2493
_reflns_observed_criterion       I>2\s(I)
_[local]_cod_data_source_file    fg1417.cif
_[local]_cod_data_source_block   I
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2007332
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O1 0.0434(7) 0.0608(10) 0.111(2) -0.0075(7) 0.0162(10) -0.0017(10)
O2 0.0684(10) 0.0619(9) 0.0869(12) 0.0085(9) -0.0115(10) -0.0266(10)
O3 0.0470(8) 0.0530(9) 0.0968(14) 0.0063(7) -0.0105(9) -0.0060(10)
C1 0.0388(9) 0.0416(9) 0.0446(10) -0.0036(7) 0.0012(8) -0.0003(8)
C2 0.0412(9) 0.0380(9) 0.0640(13) -0.0047(8) 0.0035(9) 0.0009(10)
C3 0.0445(10) 0.0457(9) 0.0538(11) -0.0023(8) 0.0031(9) 0.0019(9)
C3A 0.0466(10) 0.0389(9) 0.0471(10) 0.0015(7) -0.0016(9) 0.0038(8)
C4 0.0649(13) 0.0517(11) 0.0598(14) 0.0131(11) -0.0011(12) 0.0003(11)
C5 0.091(2) 0.0424(11) 0.064(2) 0.0151(11) -0.0131(14) -0.0006(10)
C6 0.091(2) 0.0337(10) 0.0627(15) -0.0111(10) -0.0173(14) 0.0076(10)
C7 0.0587(13) 0.0493(11) 0.0594(13) -0.0131(10) -0.0058(11) 0.0108(10)
C7A 0.0457(10) 0.0383(9) 0.0457(11) -0.0037(7) -0.0038(8) 0.0053(8)
C8 0.0413(9) 0.0451(10) 0.0611(13) -0.0014(8) -0.0016(9) -0.0045(9)
C9 0.0384(9) 0.0478(11) 0.0578(13) -0.0008(8) 0.0060(9) -0.0027(10)
loop_
_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
_atom_site_type_symbol
O1 0.69784(10) 0.2412(2) 0.5696(3) 0.0719(6) Uani d . 1 O
O2 1.03289(13) -0.0079(2) 0.3813(3) 0.0724(5) Uani d . 1 O
O3 1.14967(10) 0.0427(2) 0.5768(3) 0.0656(5) Uani d . 1 O
H3 1.157(2) -0.051(3) 0.567(4) 0.051(6) Uiso d . 1 H
C1 0.94389(13) 0.2652(2) 0.4420(3) 0.0417(4) Uani d . 1 C
C2 0.86081(13) 0.1704(2) 0.5095(3) 0.0477(5) Uani d . 1 C
C3 0.78086(14) 0.2736(2) 0.5457(3) 0.0480(5) Uani d . 1 C
C3a 0.81876(13) 0.4226(2) 0.5479(3) 0.0442(4) Uani d . 1 C
C4 0.7736(2) 0.5520(2) 0.5958(3) 0.0588(6) Uani d . 1 C
C5 0.8234(2) 0.6794(2) 0.5833(4) 0.0658(7) Uani d . 1 C
C6 0.9166(2) 0.6776(2) 0.5225(4) 0.0626(6) Uani d . 1 C
C7 0.9627(2) 0.5499(2) 0.4758(3) 0.0558(6) Uani d . 1 C
C7a 0.91256(14) 0.4192(2) 0.4886(3) 0.0433(4) Uani d . 1 C
C8 1.03914(14) 0.2275(2) 0.5256(3) 0.0492(5) Uani d . 1 C
C9 1.07195(14) 0.0756(2) 0.4834(3) 0.0480(5) Uani d . 1 C
H1A 0.94852 0.2562 0.3079 0.051(7) Uiso calc R 1 H
H2A 0.84318 0.0996 0.4163 0.072(8) Uiso calc R 1 H
H2B 0.87795 0.1186 0.6211 0.087(9) Uiso calc R 1 H
H4A 0.7110 0.5518 0.6353 0.073(8) Uiso calc R 1 H
H5A 0.7949 0.7673 0.6155 0.081(9) Uiso calc R 1 H
H6A 0.9491 0.7655 0.5128 0.059(7) Uiso calc R 1 H
H7A 1.0253 0.5511 0.4370 0.058(7) Uiso calc R 1 H
H8A 1.08591 0.2961 0.4804 0.059(7) Uiso calc R 1 H
H8B 1.03528 0.2391 0.6581 0.062(7) Uiso calc R 1 H
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
_geom_angle_publ_flag
C9 O3 H3 106.4(16) ?
C8 C1 C7A 112.4(2) ?
C8 C1 C2 114.9(2) ?
C7A C1 C2 103.36(15) ?
C3 C2 C1 106.0(2) ?
O1 C3 C3A 125.1(2) ?
O1 C3 C2 126.6(2) ?
C3A C3 C2 108.3(2) ?
C4 C3A C7A 122.2(2) ?
C4 C3A C3 128.9(2) ?
C7A C3A C3 108.9(2) ?
C5 C4 C3A 118.4(2) ?
C4 C5 C6 119.9(2) ?
C7 C6 C5 122.4(2) ?
C6 C7 C7A 118.1(2) ?
C3A C7A C7 119.0(2) ?
C3A C7A C1 111.5(2) ?
C7 C7A C1 129.5(2) ?
C9 C8 C1 113.8(2) ?
O2 C9 O3 123.6(2) ?
O2 C9 C8 125.2(2) y
O3 C9 C8 111.3(2) y
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C3 1.223(2) y
O2 C9 1.200(3) y
O3 C9 1.326(3) y
O3 H3 0.87(2) ?
C1 C8 1.517(3) ?
C1 C7A 1.518(3) ?
C1 C2 1.541(3) ?
C2 C3 1.497(3) ?
C3 C3A 1.467(3) ?
C3A C4 1.392(3) ?
C3A C7A 1.395(3) ?
C4 C5 1.367(3) ?
C5 C6 1.390(4) ?
C6 C7 1.382(3) ?
C7 C7A 1.396(3) ?
C8 C9 1.500(3) ?
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
C8 C1 C2 C3 136.1(2)
C7A C1 C2 C3 13.2(2)
C1 C2 C3 O1 166.1(2)
C1 C2 C3 C3A -13.8(2)
O1 C3 C3A C4 7.8(4)
C2 C3 C3A C4 -172.2(2)
O1 C3 C3A C7A -171.2(2)
C2 C3 C3A C7A 8.8(2)
C7A C3A C4 C5 0.2(4)
C3 C3A C4 C5 -178.6(2)
C3A C4 C5 C6 0.5(4)
C4 C5 C6 C7 -1.1(4)
C5 C6 C7 C7A 0.9(4)
C4 C3A C7A C7 -0.4(3)
C3 C3A C7A C7 178.6(2)
C4 C3A C7A C1 -179.0(2)
C3 C3A C7A C1 0.1(2)
C6 C7 C7A C3A -0.1(3)
C6 C7 C7A C1 178.2(2)
C8 C1 C7A C3A -132.9(2)
C2 C1 C7A C3A -8.4(2)
C8 C1 C7A C7 48.7(3)
C2 C1 C7A C7 173.2(2)
C7A C1 C8 C9 179.6(2)
C2 C1 C8 C9 61.7(2)
C1 C8 C9 O2 6.0(3)
C1 C8 C9 O3 -172.7(2)