#------------------------------------------------------------------------------
#$Date: 2017-10-13 02:48:21 +0200 (vie 13 de oct de 2017) $
#$Revision: 201957 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/13/2011306.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_2011306
loop_
_publ_author_name
'Chen, Chung-Der'
'Brunskill, Andrew P. J.'
'Hall, Stan S.'
'Lalancette, Roger A.'
'Thompson, Hugh W.'
_publ_section_title
;
 Phenyl- and mesitylglyoxylic acids: catemeric hydrogen bonding in two
 α-keto acids
;
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1148
_journal_page_last               1151
_journal_paper_doi               10.1107/S010827010000812X
_journal_volume                  56
_journal_year                    2000
_chemical_formula_moiety         'C8 H6 O3'
_chemical_formula_sum            'C8 H6 O3'
_chemical_formula_weight         150.13
_chemical_melting_point          342
_chemical_name_common            'phenylglyoxylic acid'
_chemical_name_systematic
;
α-Oxobenzeneacetic acid
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 115.32(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.462(2)
_cell_length_b                   16.513(5)
_cell_length_c                   6.483(3)
_cell_measurement_reflns_used    15
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      12.3
_cell_measurement_theta_min      3.2
_cell_volume                     722.1(5)
_computing_cell_refinement       XSCANS
_computing_data_collection       'XSCANS (Siemens, 1996)'
_computing_data_reduction        XSCANS
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full .998
_diffrn_measured_fraction_theta_max .998
_diffrn_measurement_device_type  'Siemens P4'
_diffrn_measurement_method       '2θ-θ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     .71073
_diffrn_reflns_av_R_equivalents  .022
_diffrn_reflns_av_sigmaI/netI    .047
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -1
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -1
_diffrn_reflns_number            1562
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.47
_diffrn_standards_decay_%        'variation < 1.8'
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    .107
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             312
_exptl_crystal_size_max          .64
_exptl_crystal_size_mid          .50
_exptl_crystal_size_min          .30
_refine_diff_density_max         .20
_refine_diff_density_min         -.19
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.05
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     105
_refine_ls_number_reflns         1271
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.05
_refine_ls_R_factor_all          .114
_refine_ls_R_factor_gt           .059
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         .00
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0743P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .153
_reflns_number_gt                740
_reflns_number_total             1271
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fg1604.cif
_cod_data_source_block           I
_cod_original_cell_volume        722.1(4)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2011306
_cod_database_fobs_code          2011306
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_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
_atom_site_type_symbol
O1 .1528(4) .62379(13) .4709(4) .0711(7) Uani d . 1 . . O
O2 .3784(4) .68636(14) .1497(4) .0777(8) Uani d . 1 . . O
O3 .0991(3) .73600(13) .1469(4) .0667(7) Uani d . 1 . . O
H3 .125(6) .780(3) .075(7) .123(16) Uiso d . 1 . . H
C1 .2363(4) .52537(16) .2631(5) .0510(8) Uani d . 1 . . C
C2 .2801(5) .50725(19) .0795(6) .0617(9) Uani d . 1 . . C
C3 .3127(5) .4272(2) .0415(7) .0761(11) Uani d . 1 . . C
C4 .3020(5) .3672(2) .1792(8) .0807(12) Uani d . 1 . . C
C5 .2541(5) .3844(2) .3572(7) .0808(12) Uani d . 1 . . C
C6 .2219(5) .46344(18) .3989(6) .0645(9) Uani d . 1 . . C
C7 .2028(4) .60937(17) .3189(5) .0523(8) Uani d . 1 . . C
C8 .2376(5) .68093(17) .1917(5) .0555(8) Uani d . 1 . . C
H2 .2872 .5481 -.0155 .085(5) Uiso calc R 1 . . H
H3A .3424 .4143 -.0801 .085(5) Uiso calc R 1 . . H
H4 .3274 .3140 .1530 .085(5) Uiso calc R 1 . . H
H5 .2436 .3430 .4485 .085(5) Uiso calc R 1 . . H
H6 .1901 .4754 .5195 .085(5) Uiso calc R 1 . . H
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 .1039(18) .0484(13) .0811(16) -.0081(11) .0588(15) -.0032(12)
O2 .0759(16) .0660(15) .108(2) .0024(12) .0554(15) .0166(13)
O3 .0732(15) .0471(12) .0856(18) .0051(11) .0396(13) .0091(12)
C1 .0442(17) .0442(16) .058(2) -.0009(13) .0156(15) .0034(15)
C2 .058(2) .059(2) .069(2) -.0046(15) .0283(18) -.0027(17)
C3 .067(2) .069(2) .088(3) .0021(19) .029(2) -.023(2)
C4 .064(2) .044(2) .119(4) .0031(16) .025(2) -.010(2)
C5 .083(3) .0471(19) .103(3) -.0015(18) .031(2) .014(2)
C6 .067(2) .0499(18) .074(2) -.0034(15) .0280(19) .0026(17)
C7 .0517(18) .0452(17) .061(2) -.0049(13) .0250(16) .0012(16)
C8 .0580(19) .0433(16) .065(2) -.0037(15) .0262(17) -.0020(15)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0106 .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
C6 C1 C2 119.7(3) ?
C6 C1 C7 118.0(3) ?
C2 C1 C7 122.3(3) ?
C3 C2 C1 118.7(3) ?
C4 C3 C2 121.0(4) ?
C3 C4 C5 120.7(3) ?
C6 C5 C4 119.4(3) ?
C5 C6 C1 120.6(3) ?
O1 C7 C1 121.5(3) ?
O1 C7 C8 117.9(3) ?
C1 C7 C8 120.6(3) ?
O2 C8 O3 125.7(3) ?
O2 C8 C7 123.4(3) y
O3 C8 C7 110.9(3) y
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 C7 . 1.217(3) y
O2 C8 . 1.196(3) y
O3 C8 . 1.312(4) y
C1 C6 . 1.383(4) ?
C1 C2 . 1.395(4) ?
C1 C7 . 1.481(4) ?
C2 C3 . 1.386(4) ?
C3 C4 . 1.358(5) ?
C4 C5 . 1.376(5) ?
C5 C6 . 1.374(5) ?
C7 C8 . 1.525(4) ?
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
C6 C1 C2 C3 -1.5(5)
C7 C1 C2 C3 178.9(3)
C1 C2 C3 C4 .2(5)
C2 C3 C4 C5 1.4(5)
C3 C4 C5 C6 -1.7(5)
C4 C5 C6 C1 .3(5)
C2 C1 C6 C5 1.3(5)
C7 C1 C6 C5 -179.1(3)
C6 C1 C7 O1 -4.2(4)
C2 C1 C7 O1 175.4(3)
C6 C1 C7 C8 173.6(3)
C2 C1 C7 C8 -6.8(4)
O1 C7 C8 O2 134.3(3)
C1 C7 C8 O2 -43.6(4)
O1 C7 C8 O3 -42.5(4)
C1 C7 C8 O3 139.6(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 11421
