#------------------------------------------------------------------------------
#$Date: 2016-02-19 16:29:56 +0200 (Fri, 19 Feb 2016) $
#$Revision: 176759 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/65/2006584.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_2006584
loop_
_publ_author_name
'Okabe, Nobuo '
' Inubushi, Chika'
_publ_contact_author
; Nobuo Okabe
Faculty of Pharmaceutical Sciences
Kinki University
Kowakae 3-4-1
Higashiosaka
Osaka 577
Japan
;
_publ_section_title
;
 Phenylpyruvic Acid
;
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1449
_journal_page_last               1450
_journal_paper_doi               10.1107/S0108270197006525
_journal_volume                  53
_journal_year                    1997
_chemical_formula_moiety         'C9 H8 O3'
_chemical_formula_sum            'C9 H8 O3'
_chemical_formula_weight         164.16
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_space_group_name_H-M   'P 1 21/a 1'
_atom_type_scat_source
'International Tables for X-ray Crystallography Vol.IV'
_cell_angle_alpha                90
_cell_angle_beta                 91.30(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.4890(10)
_cell_length_b                   5.534(4)
_cell_length_c                   18.722(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    296
_cell_measurement_theta_max      19.59
_cell_measurement_theta_min      15.34
_cell_volume                     775.7(6)
_computing_cell_refinement       'MSC/AFC Diffractometer Control Software'
_computing_data_collection
;
MSC/AFC Diffractometer Control Software
(Molecular Structure Corporation, 1988)
;
_computing_data_reduction
'TEXSAN (Molecular Structure Corporation, 1985)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_structure_refinement  TEXSAN
_computing_structure_solution
'MITHRIL (Gilmore, 1984), DIRDIF (Beurskens, 1984)'
_diffrn_measurement_device       'Rigaku AFC5R'
_diffrn_measurement_method       ω-2θ
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.061
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            2110
_diffrn_reflns_theta_max         27.5
_diffrn_standards_decay_%        2.76
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.405
_exptl_crystal_density_meas      ?
_exptl_crystal_description       plate
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.27
_refine_diff_density_min         -0.35
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_obs   2.160
_refine_ls_hydrogen_treatment    'H atoms refined isotropically'
_refine_ls_number_parameters     141
_refine_ls_number_reflns         1301
_refine_ls_R_factor_obs          .057
_refine_ls_shift/esd_max         0.007
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = 4Fₒ²/σ²(Fₒ²)'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_obs         .070
_reflns_number_observed          1301
_reflns_number_total             1964
_reflns_observed_criterion       I>1.5\s(I)
_cod_data_source_file            fr1047.cif
_cod_data_source_block           global
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not determined' was changed to
'?' - the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'w = 4F~o~^2^/\s^2^(F~o~^2^)' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to 'w =
4F~o~^2^/\s^2^(F~o~^2^)'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        776.0(10)
_cod_original_sg_symbol_H-M      'P 21/a'
_cod_database_code               2006584
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
1/2-x,1/2+y,-z
-x,-y,-z
1/2+x,1/2-y,z
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 .089(2) .0490(10) .0260(10) .0090(10) -.0270(10) .0020(10)
O2 .090(2) .0560(10) .0270(10) -.0050(10) -.0250(10) -.0070(10)
O3 .091(2) .0360(10) .0340(10) .0050(10) -.0270(10) -.0055(9)
C1 .0330(10) .0300(10) .0190(10) -.0040(10) -.0070(10) .0000(10)
C2 .0400(10) .0300(10) .0250(10) .0020(10) -.0110(10) -.0010(10)
C3 .0430(10) .043(2) .0220(10) -.0030(10) -.0080(10) -.0070(10)
C4 .0410(10) .047(2) .0210(10) -.0050(10) -.0110(10) .0040(10)
C5 .0400(10) .0360(10) .0310(10) .0040(10) -.0130(10) .0070(10)
C6 .0380(10) .0330(10) .0250(10) .0010(10) -.0080(10) -.0010(10)
C7 .0450(10) .0320(10) .0210(10) .0000(10) -.0110(10) .0020(10)
C8 .0470(10) .0340(10) .0240(10) -.0010(10) -.0110(10) .0010(10)
C9 .051(2) .046(2) .0200(10) -.0010(10) -.0110(10) -.0010(10)
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
O1 -.1587(3) .2380(4) .57920(10)
O2 -.1713(3) -.1479(4) .54330(10)
O3 -.0149(3) -.3091(4) .66170(10)
C1 .0489(3) .0375(4) .78310(10)
C2 .0162(3) .2110(5) .83520(10)
C3 .0714(3) .1737(5) .90580(10)
C4 .1621(3) -.0332(5) .92440(10)
C5 .1994(3) -.2044(5) .87310(10)
C6 .1420(3) -.1714(5) .80270(10)
C7 -.0201(3) .0865(5) .71060(10)
C8 -.0495(3) -.0692(5) .65680(10)
C9 -.1322(4) .0056(5) .58790(10)
H2 -.047(3) .355(5) .8260(10)
H3 .047(3) .299(5) .939(2)
H4 .204(4) -.061(5) .973(2)
H5 .263(3) -.347(5) .8850(10)
H6 .169(4) -.299(6) .765(2)
H7 -.057(4) .250(6) .704(2)
H8 -.064(5) -.391(7) .620(2)
H9 -.225(6) .258(8) .540(2)
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
C2 C1 C6 118.7(2) yes
C2 C1 C7 117.2(2) yes
C6 C1 C7 124.1(2) yes
C1 C2 C3 120.6(2) yes
C2 C3 C4 120.0(2) yes
C3 C4 C5 120.1(2) yes
C4 C5 C6 120.4(2) yes
C1 C6 C5 120.1(2) yes
C1 C7 C8 128.6(2) yes
O3 C8 C7 123.5(2) yes
O3 C8 C9 114.1(2) yes
C7 C8 C9 122.3(2) yes
O1 C9 O2 124.4(2) yes
O1 C9 C8 116.2(2) yes
O2 C9 C8 119.4(2) yes
C9 O1 H9 108(3) no
C8 O3 H8 110(2) no
C1 C2 H2 123(2) no
C3 C2 H2 116(2) no
C2 C3 H3 117(2) no
C4 C3 H3 123(2) no
C3 C4 H4 121(2) no
C5 C4 H4 119(2) no
C4 C5 H5 121(2) no
C6 C5 H5 118(2) no
C1 C6 H6 119(2) no
C5 C6 H6 121(2) no
C1 C7 H7 113(2) no
C8 C7 H7 118(2) 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 C9 . . 1.311(3) yes
O2 C9 . . 1.222(3) yes
O3 C8 . . 1.355(3) yes
C1 C2 . . 1.395(3) yes
C1 C6 . . 1.395(3) yes
C1 C7 . . 1.467(3) yes
C2 C3 . . 1.391(3) yes
C3 C4 . . 1.373(4) yes
C4 C5 . . 1.382(4) yes
C5 C6 . . 1.388(3) yes
C7 C8 . . 1.339(3) yes
C8 C9 . . 1.479(3) yes
O1 H9 . . .88(5) no
O3 H8 . . .97(4) no
C2 H2 . . .94(2) no
C3 H3 . . .95(3) no
C4 H4 . . .97(3) no
C5 H5 . . .95(3) no
C6 H6 . . 1.03(3) no
C7 H7 . . .95(3) no
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
_geom_torsion_publ_flag
O1 C9 C8 O3 -176.2(3) no
O1 C9 C8 C7 6.8(4) no
O2 C9 C8 O3 3.8(4) no
O2 C9 C8 C7 -173.1(3) no
O3 C8 C7 C1 -1.1(5) no
C1 C2 C3 C4 1.3(4) no
C1 C6 C5 C4 1.1(4) no
C1 C7 C8 C9 175.5(3) no
C2 C1 C6 C5 0.4(4) no
C2 C1 C7 C8 -160.5(3) no
C2 C3 C4 C5 0.3(4) no
C3 C2 C1 C6 -1.6(4) no
C3 C2 C1 C7 177.6(2) no
C3 C4 C5 C6 -1.5(4) no
C5 C6 C1 C7 -178.7(2) no
C6 C1 C7 C8 18.6(4) no
