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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/2/22/70/2227011.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_2227011
loop_
_publ_author_name
'Cheng, Po-Wen'
'Cheng, Chi-Feng'
'Chun-Ting, Yeh'
'Lin, Chia-Her'
_publ_section_title
;
 2,5-Dihydroxyterephthalic acid dihydrate
;
_journal_coeditor_code           NC2191
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1928
_journal_paper_doi               10.1107/S1600536810025766
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C8 H6 O6 , 2H2 O'
_chemical_formula_moiety         'C8 H6 O6 , 2H2 O'
_chemical_formula_sum            'C8 H10 O8'
_chemical_formula_weight         234.16
_chemical_name_common
;
2,5-dihydroxyterephthalic acid dihydrate
;
_chemical_name_systematic
;
2,5-dihydroxybenzene-1,4-dicarboxylic acid dihydrate
;
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 103.030(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   5.1883(10)
_cell_length_b                   17.545(4)
_cell_length_c                   5.4990(12)
_cell_measurement_reflns_used    760
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      22.50
_cell_measurement_theta_min      2.32
_cell_volume                     487.68(18)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      295(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0797
_diffrn_reflns_av_sigmaI/netI    0.0947
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       4
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            4475
_diffrn_reflns_theta_full        28.40
_diffrn_reflns_theta_max         28.40
_diffrn_reflns_theta_min         2.32
_exptl_absorpt_coefficient_mu    0.147
_exptl_absorpt_correction_T_max  0.963
_exptl_absorpt_correction_T_min  0.945
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            light-yellow
_exptl_crystal_density_diffrn    1.595
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       tablular
_exptl_crystal_F_000             244
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.356
_refine_diff_density_min         -0.317
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     73
_refine_ls_number_reflns         1208
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.1348
_refine_ls_R_factor_gt           0.0605
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0851P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1628
_refine_ls_wR_factor_ref         0.1926
_reflns_number_gt                589
_reflns_number_total             1208
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            nc2191.cif
_cod_data_source_block           I
_cod_original_cell_volume        487.68(17)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2227011
_cod_database_fobs_code          2227011
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_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
O O1 0.0253(5) 0.35101(13) 0.8449(4) 0.0561(7) Uani d . 1 . .
H H1A -0.0615 0.3231 0.9153 0.084 Uiso calc R 1 . .
O O2 0.4188(5) 0.59034(13) 0.6391(4) 0.0488(7) Uani d . 1 . .
H H2B 0.4915 0.6261 0.5857 0.073 Uiso calc R 1 . .
O O3 0.2796(5) 0.68281(14) 0.8554(4) 0.0536(7) Uani d . 1 . .
O O1W 0.6537(4) 0.69917(13) 1.4663(4) 0.0524(7) Uani d . 1 . .
H H1WA 0.5399 0.7288 1.3796 0.079 Uiso d . 1 . .
H H1WB 0.7486 0.6811 1.3724 0.079 Uiso d . 1 . .
C C1 0.0087(6) 0.42428(18) 0.9234(5) 0.0371(8) Uani d . 1 . .
C C2 0.1432(6) 0.48027(18) 0.8263(5) 0.0394(9) Uani d . 1 . .
H H2A 0.2394 0.4671 0.7089 0.047 Uiso calc R 1 . .
C C3 0.2843(6) 0.61572(19) 0.7961(5) 0.0378(8) Uani d . 1 . .
C C4 0.1382(6) 0.55608(17) 0.9001(5) 0.0337(8) Uani d . 1 . .
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 0.0761(17) 0.0361(15) 0.0720(15) -0.0063(12) 0.0504(14) -0.0070(12)
O2 0.0610(15) 0.0415(15) 0.0545(14) -0.0033(11) 0.0352(12) 0.0004(11)
O3 0.0678(17) 0.0402(15) 0.0639(16) -0.0083(12) 0.0380(13) -0.0066(12)
O1W 0.0646(16) 0.0461(16) 0.0575(14) 0.0068(12) 0.0371(13) 0.0091(12)
C1 0.0391(18) 0.037(2) 0.0386(16) 0.0007(14) 0.0155(14) -0.0015(14)
C2 0.0412(19) 0.043(2) 0.0399(17) 0.0012(15) 0.0208(15) -0.0001(15)
C3 0.0377(18) 0.041(2) 0.0366(17) -0.0011(15) 0.0131(14) 0.0051(15)
C4 0.0338(17) 0.0363(19) 0.0324(15) 0.0026(13) 0.0105(13) 0.0015(13)
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
C1 O1 H1A . . 109.5 ?
C3 O2 H2B . . 109.5 ?
H1WA O1W H1WB . . 108.2 ?
O1 C1 C2 . . 118.3(3) ?
O1 C1 C4 . 3_567 122.1(3) ?
C2 C1 C4 . 3_567 119.5(3) ?
C1 C2 C4 . . 121.5(3) ?
C1 C2 H2A . . 119.2 ?
C4 C2 H2A . . 119.2 ?
O3 C3 O2 . . 123.4(3) ?
O3 C3 C4 . . 122.3(3) ?
O2 C3 C4 . . 114.3(3) ?
C2 C4 C1 . 3_567 119.0(3) ?
C2 C4 C3 . . 121.2(3) ?
C1 C4 C3 3_567 . 119.9(3) ?
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 C1 . 1.365(4) ?
O1 H1A . 0.8200 ?
O2 C3 . 1.305(3) ?
O2 H2B . 0.8200 ?
O3 C3 . 1.223(4) ?
O1W H1WA . 0.8485 ?
O1W H1WB . 0.8511 ?
C1 C2 . 1.380(4) ?
C1 C4 3_567 1.405(4) ?
C2 C4 . 1.393(4) ?
C2 H2A . 0.9300 ?
C3 C4 . 1.480(4) ?
C4 C1 3_567 1.406(4) ?
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
O1 H1A O3 3_567 0.82 1.88 2.597(3) 146.0
O2 H2B O1W 1_554 0.82 1.74 2.561(3) 177.4
O1W H1WB O1 3_667 0.85 1.94 2.786(3) 175.0
O1W H1WA O3 4_576 0.85 2.04 2.809(3) 150.4
