#------------------------------------------------------------------------------
#$Date: 2011-09-10 06:16:28 +0300 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2200548.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_2200548
loop_
_publ_author_name
'Okabe, Nobuo'
'Kyoyama, Hasuyo'
_publ_section_title
;
 3,4-Dihydroxyphenylacetic acid
;
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o715
_journal_page_last               o716
_journal_volume                  57
_journal_year                    2001
_chemical_formula_iupac          'C8 H8 O4'
_chemical_formula_moiety         'C8 H8 O4'
_chemical_formula_sum            'C8 H8 O4'
_chemical_formula_weight         168.14
_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'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   16.181(2)
_cell_length_b                   11.625(2)
_cell_length_c                   7.938(3)
_cell_measurement_reflns_used    18
_cell_measurement_temperature    296.2
_cell_measurement_theta_max      13.1
_cell_measurement_theta_min      10.1
_cell_volume                     1493.2(6)
_computing_cell_refinement
;MSC/AFC(Molecular Structure Corporation,
Rigaku Corporation, 1999)
;
_computing_data_collection
;MSC/AFC(Molecular Structure Corporation,
Rigaku Corporation, 1999)
;
_computing_data_reduction
;TEXSAN Version 1.10 (Molecular Structure Corporation,
Rigaku Corporation, 1999)
;
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material
;TEXSAN Version 1.10 (Molecular Structure Corporation,
Rigaku Corporation, 1999)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution
;SIR88 (Burla et al., 1989) & DIRDIF94
(Beurskens et al., 1994)
;
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Rigaku AFC-5R'
_diffrn_measurement_method       \w-2\q
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     .7107
_diffrn_reflns_av_R_equivalents  .000
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       0
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            1714
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         4
_diffrn_standards_decay_%        .22
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    .122
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.496
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'thin plate'
_exptl_crystal_F_000             704.00
_exptl_crystal_size_max          .350
_exptl_crystal_size_mid          .200
_exptl_crystal_size_min          .020
_refine_diff_density_max         .25
_refine_diff_density_min         -.30
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   .842
_refine_ls_hydrogen_treatment    noref
_refine_ls_number_parameters     109
_refine_ls_number_reflns         1714
_refine_ls_R_factor_gt           .0511
_refine_ls_shift/su_max          <0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^) + (0.1P)^2^] where P = (Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .2202
_reflns_number_gt                493
_reflns_number_total             1714
_reflns_threshold_expression     I>2\s(I)
_[local]_cod_data_source_file    wn6027.cif
_[local]_cod_data_source_block   I
_cod_database_code               2200548
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
1/2+x,1/2-y,-z
-x,1/2+y,1/2-z
1/2-x,-y,1/2+z
-x,-y,-z
1/2-x,1/2+y,z
x,1/2-y,1/2+z
1/2+x,y,1/2-z
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_occupancy
_atom_site_type_symbol
O1 .9152(2) -.0207(3) .3666(6) .0550(10) Uani d 1.00 O
O2 .9798(2) .1389(4) .4402(5) .0460(10) Uani d 1.00 O
O3 .5970(2) -.0461(3) .3061(5) .0470(10) Uani d 1.00 O
O4 .5340(2) .1330(3) .4918(5) .0420(10) Uani d 1.00 O
C1 .7766(3) .1434(5) .3191(7) .0290(10) Uani d 1.00 C
C2 .7254(3) .0496(5) .2849(7) .0340(10) Uani d 1.00 C
C3 .6453(3) .0468(4) .3444(7) .0330(10) Uani d 1.00 C
C4 .6155(3) .1381(5) .4406(6) .0320(10) Uani d 1.00 C
C5 .6653(3) .2295(5) .4787(8) .0380(10) Uani d 1.00 C
C6 .7463(3) .2324(5) .4162(7) .0370(10) Uani d 1.00 C
C7 .8644(3) .1493(5) .2511(7) .0380(10) Uani d 1.00 C
C8 .9250(3) .0904(5) .3625(8) .0340(10) Uani d 1.00 C
H2 .7460 -.0133 .2208 .0406 Uiso calc 1.00 H
H3 .5458 -.0298 .3404 .0464 Uiso calc 1.00 H
H4 .4987 .1916 .5362 .0464 Uiso calc 1.00 H
H5 .6452 .2904 .5471 .0453 Uiso calc 1.00 H
H6 .7808 .2963 .4406 .0445 Uiso calc 1.00 H
H7 .8798 .2278 .2406 .0450 Uiso calc 1.00 H
H8 .8658 .1137 .1434 .0450 Uiso calc 1.00 H
H9 .9579 -.0777 .4190 .0464 Uiso calc 1.00 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 .046(2) .035(2) .083(3) .001(2) -.023(2) .005(2)
O2 .031(2) .041(2) .066(3) -.005(2) -.012(2) .004(2)
O3 .034(2) .034(2) .075(3) -.005(2) .010(2) -.008(2)
O4 .026(2) .039(2) .060(3) .002(2) .005(2) -.007(2)
C1 .022(2) .037(3) .030(3) .002(2) -.002(2) .008(3)
C2 .029(3) .028(3) .046(4) .003(2) .006(3) .001(3)
C3 .032(3) .028(3) .039(3) -.004(2) -.008(3) .004(3)
C4 .026(2) .034(3) .036(3) .006(3) .005(2) .003(3)
C5 .039(3) .034(3) .042(4) .003(3) -.003(3) -.011(3)
C6 .027(2) .034(3) .052(4) -.008(3) -.006(3) -.005(3)
C7 .031(3) .044(3) .041(3) -.003(3) -.001(2) .005(3)
C8 .025(3) .034(3) .043(4) .004(3) .003(3) .001(3)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .003 .002
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H .000 .000
;International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
O O .011 .006
;International Tables for Crystallography
(1992, 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_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C8 O1 H9 1_555 1_555 124.0 no
C3 O3 H3 1_555 1_555 107.2 no
C4 O4 H4 1_555 1_555 130.4 no
C2 C1 C6 1_555 1_555 118.9(4) yes
C2 C1 C7 1_555 1_555 121.4(5) yes
C6 C1 C7 1_555 1_555 119.7(5) yes
C1 C2 C3 1_555 1_555 120.6(5) yes
C1 C2 H2 1_555 1_555 119.7 no
C3 C2 H2 1_555 1_555 119.7 no
O3 C3 C2 1_555 1_555 118.7(5) yes
O3 C3 C4 1_555 1_555 121.6(4) yes
C2 C3 C4 1_555 1_555 119.7(5) yes
O4 C4 C3 1_555 1_555 117.3(5) yes
O4 C4 C5 1_555 1_555 122.1(5) yes
C3 C4 C5 1_555 1_555 120.6(5) yes
C4 C5 C6 1_555 1_555 119.4(5) yes
C4 C5 H5 1_555 1_555 120.3 no
C6 C5 H5 1_555 1_555 120.3 no
C1 C6 C5 1_555 1_555 120.8(5) yes
C1 C6 H6 1_555 1_555 119.5 no
C5 C6 H6 1_555 1_555 119.8 no
C1 C7 C8 1_555 1_555 112.6(5) yes
C1 C7 H7 1_555 1_555 108.7 no
C1 C7 H8 1_555 1_555 108.8 no
C8 C7 H7 1_555 1_555 108.7 no
C8 C7 H8 1_555 1_555 108.6 no
H7 C7 H8 1_555 1_555 109.5 no
O1 C8 O2 1_555 1_555 122.4(5) yes
O1 C8 C7 1_555 1_555 113.0(5) yes
O2 C8 C7 1_555 1_555 124.6(5) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C8 1.301(7) yes
O1 H9 1.044 no
O2 C8 1.219(7) yes
O3 C3 1.368(6) yes
O3 H3 .891 no
O4 C4 1.381(6) yes
O4 H4 .957 no
C1 C2 1.397(7) yes
C1 C6 1.381(8) yes
C1 C7 1.520(7) yes
C2 C3 1.379(7) yes
C2 H2 .951 no
C3 C4 1.394(8) yes
C4 C5 1.367(8) yes
C5 C6 1.402(7) yes
C5 H5 .950 no
C6 H6 .948 no
C7 C8 1.489(8) yes
C7 H7 .950 no
C7 H8 .950 no
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_2
O1 O2 2.670(6) 5_756
O1 O3 3.258(5) 8_555
O1 C5 3.305(7) 6_645
O1 O4 3.351(6) 4_654
O1 C8 3.459(7) 5_756
O1 O1 3.500(8) 5_756
O1 O3 3.580(6) 4_655
O2 O4 2.845(6) 2_556
O2 O3 3.339(6) 4_655
O2 C5 3.429(6) 2_556
O2 O2 3.430(8) 5_756
O2 C8 3.454(7) 5_756
O2 O3 3.470(5) 8_555
O2 C4 3.526(7) 2_556
O2 O4 3.540(6) 8_555
O3 O4 2.844(5) 5_656
O3 C8 3.471(6) 8_455
O3 C8 3.577(7) 4_654
O4 O4 3.284(7) 5_656
O4 C8 3.357(7) 8_455
O4 C7 3.361(6) 8_455
C1 C6 3.543(8) 7_554
C1 C5 3.568(8) 7_554
C6 C7 3.550(8) 7_555
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
O1 H9 O2 5_756 1.046 1.667 2.674(6) 160.1 yes
O3 H3 O4 1_555 .891 2.248 2.745(5) 114.8 yes
O4 H4 O2 2_456 .957 2.000 2.843(6) 145.8 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
O1 C8 C7 C1 1_555 1_555 1_555 1_555 68.1(6) yes
O2 C8 C7 C1 1_555 1_555 1_555 1_555 -113.5(6) yes
O3 C3 C2 C1 1_555 1_555 1_555 1_555 179.2(5) yes
O3 C3 C4 O4 1_555 1_555 1_555 1_555 -1.9(7) yes
O3 C3 C4 C5 1_555 1_555 1_555 1_555 179.3(5) yes
O4 C4 C3 C2 1_555 1_555 1_555 1_555 177.7(5) yes
O4 C4 C5 C6 1_555 1_555 1_555 1_555 -176.9(5) yes
C1 C2 C3 C4 1_555 1_555 1_555 1_555 -.4(8) yes
C1 C6 C5 C4 1_555 1_555 1_555 1_555 -1.0(8) yes
C2 C1 C6 C5 1_555 1_555 1_555 1_555 -.4(8) yes
C2 C1 C7 C8 1_555 1_555 1_555 1_555 -86.2(6) yes
C2 C3 C4 C5 1_555 1_555 1_555 1_555 -1.1(8) yes
C3 C2 C1 C6 1_555 1_555 1_555 1_555 1.1(8) yes
C3 C2 C1 C7 1_555 1_555 1_555 1_555 -178.5(5) yes
C3 C4 C5 C6 1_555 1_555 1_555 1_555 1.8(8) yes
C5 C6 C1 C7 1_555 1_555 1_555 1_555 179.3(5) yes
C6 C1 C7 C8 1_555 1_555 1_555 1_555 94.1(6) yes