#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/40/2234081.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_2234081
loop_
_publ_author_name
'Li, Jin-Hang'
'Dong, Fu-Yue'
'Cai, Fang'
'Yuan, Xiao-Feng'
'Jiang, Ren-Wang'
_publ_section_title
;
 2,3,4-Trihydroxybenzoic acid 0.25-hydrate
;
_journal_coeditor_code           ZS2181
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o825
_journal_page_last               o826
_journal_paper_doi               10.1107/S160053681200709X
_journal_volume                  68
_journal_year                    2012
_chemical_formula_moiety         'C7 H6 O5, 0.25H2 O'
_chemical_formula_sum            'C7 H6.5 O5.25'
_chemical_formula_weight         174.62
_chemical_name_systematic
;
2,3,4-Trihydroxybenzoic acid 0.25-hydrate
;
_space_group_IT_number           18
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2 2ab'
_symmetry_space_group_name_H-M   'P 21 21 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   11.8364(12)
_cell_length_b                   32.598(3)
_cell_length_c                   3.7306(4)
_cell_measurement_reflns_used    2552
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      50.00
_cell_measurement_theta_min      2.13
_cell_volume                     1439.4(3)
_computing_cell_refinement       'SAINT (Bruker, 1998)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAINT (Bruker, 1998)'
_computing_molecular_graphics    'XP (Siemens, 1998)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      291(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker SMART 1000 CCD'
_diffrn_measurement_method       'ω scan'
_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  0.0596
_diffrn_reflns_av_sigmaI/netI    0.0504
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_k_min       -38
_diffrn_reflns_limit_l_max       4
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_number            7863
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.13
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.142
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.874
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'
_exptl_crystal_colour            'light brown'
_exptl_crystal_density_diffrn    1.612
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             724
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.165
_refine_diff_density_min         -0.152
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.966
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     222
_refine_ls_number_reflns         2552
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.966
_refine_ls_R_factor_all          0.0510
_refine_ls_R_factor_gt           0.0358
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0443P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0842
_refine_ls_wR_factor_ref         0.0904
_reflns_number_gt                2010
_reflns_number_total             2552
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            zs2181.cif
_cod_data_source_block           I
_cod_original_sg_symbol_Hall     'P 2ac 2ab'
_cod_database_code               2234081
_cod_database_fobs_code          2234081
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'-x+1/2, y+1/2, -z'
'x+1/2, -y+1/2, -z'
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_symmetry_multiplicity
O O1W 0.5000 0.0000 -0.1102(7) 0.0395(6) Uani d S 1 2
H H1WA 0.5263 0.0173 0.0258 0.059 Uiso calc R 1 1
O O1 0.65345(12) 0.12870(4) 0.2193(5) 0.0334(4) Uani d . 1 1
H H1A 0.6637 0.1534 0.1900 0.040 Uiso calc R 1 1
O O2 0.65656(13) 0.04688(4) 0.3549(4) 0.0323(4) Uani d . 1 1
H H2A 0.6145 0.0640 0.4444 0.039 Uiso calc R 1 1
O O3 0.84576(14) 0.00203(5) 0.2010(5) 0.0445(5) Uani d . 1 1
H H3A 0.7859 -0.0048 0.2940 0.053 Uiso calc R 1 1
O O4 0.75826(14) 0.19200(4) -0.0346(6) 0.0429(5) Uani d . 1 1
O O5 0.93058(15) 0.18491(4) -0.2704(6) 0.0481(5) Uani d . 1 1
H H5B 0.9243 0.2098 -0.2919 0.058 Uiso calc R 1 1
C C1 0.84467(19) 0.12653(6) -0.0250(7) 0.0273(5) Uani d . 1 1
C C2 0.74982(19) 0.10787(6) 0.1337(6) 0.0245(5) Uani d . 1 1
C C3 0.74932(18) 0.06626(6) 0.2074(6) 0.0254(5) Uani d . 1 1
C C4 0.84311(19) 0.04271(6) 0.1272(7) 0.0295(5) Uani d . 1 1
C C5 0.9374(2) 0.06046(7) -0.0324(7) 0.0330(6) Uani d . 1 1
H H5A 0.9998 0.0444 -0.0891 0.040 Uiso calc R 1 1
C C6 0.9383(2) 0.10180(7) -0.1064(7) 0.0313(6) Uani d . 1 1
H H6A 1.0018 0.1135 -0.2117 0.038 Uiso calc R 1 1
C C7 0.8406(2) 0.17017(7) -0.1079(7) 0.0310(6) Uani d . 1 1
O O1' 0.49399(13) 0.17376(4) -0.2824(5) 0.0359(4) Uani d . 1 1
H H1'A 0.4856 0.1982 -0.3270 0.043 Uiso calc R 1 1
O O2' 0.49999(12) 0.09083(4) -0.2151(5) 0.0308(4) Uani d . 1 1
H H2'A 0.5380 0.1075 -0.1033 0.037 Uiso calc R 1 1
O O3' 0.32290(14) 0.04439(4) -0.4474(5) 0.0397(5) Uani d . 1 1
H H3'A 0.3817 0.0378 -0.3464 0.048 Uiso calc R 1 1
O O4' 0.39072(15) 0.23703(5) -0.5434(6) 0.0446(5) Uani d . 1 1
O O5' 0.22055(15) 0.23003(5) -0.7935(6) 0.0506(5) Uani d . 1 1
H H5'B 0.2294 0.2547 -0.8259 0.061 Uiso calc R 1 1
C C1' 0.3088(2) 0.17066(7) -0.5659(7) 0.0293(6) Uani d . 1 1
C C2' 0.40325(19) 0.15242(6) -0.4052(6) 0.0271(6) Uani d . 1 1
C C3' 0.40863(19) 0.11019(6) -0.3646(6) 0.0267(5) Uani d . 1 1
C C4' 0.31874(19) 0.08593(6) -0.4795(7) 0.0281(6) Uani d . 1 1
C C5' 0.22322(19) 0.10389(7) -0.6322(7) 0.0328(6) Uani d . 1 1
H H5'A 0.1630 0.0876 -0.7056 0.039 Uiso calc R 1 1
C C6' 0.2185(2) 0.14569(7) -0.6737(7) 0.0336(6) Uani d . 1 1
H H6'A 0.1546 0.1576 -0.7746 0.040 Uiso calc R 1 1
C C7' 0.3098(2) 0.21492(7) -0.6310(7) 0.0349(6) Uani d . 1 1
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
C2 O1 H1A 109.5
C3 O2 H2A 109.5
C4 O3 H3A 109.5
C7 O5 H5B 109.5
C6 C1 C2 118.2(2)
C6 C1 C7 122.8(2)
C2 C1 C7 119.0(2)
O1 C2 C3 115.9(2)
O1 C2 C1 123.35(18)
C3 C2 C1 120.7(2)
O2 C3 C4 118.08(17)
O2 C3 C2 122.06(19)
C4 C3 C2 119.9(2)
O3 C4 C3 121.2(2)
O3 C4 C5 118.4(2)
C3 C4 C5 120.4(2)
C6 C5 C4 119.9(2)
C6 C5 H5A 120.0
C4 C5 H5A 120.0
C5 C6 C1 120.9(2)
C5 C6 H6A 119.6
C1 C6 H6A 119.6
O4 C7 O5 122.0(2)
O4 C7 C1 122.7(2)
O5 C7 C1 115.3(2)
C2' O1' H1'A 109.5
C3' O2' H2'A 109.5
C4' O3' H3'A 109.5
C7' O5' H5'B 109.5
C2' C1' C6' 119.0(2)
C2' C1' C7' 118.9(2)
C6' C1' C7' 122.1(2)
O1' C2' C3' 115.8(2)
O1' C2' C1' 123.89(18)
C3' C2' C1' 120.3(2)
O2' C3' C2' 122.5(2)
O2' C3' C4' 117.79(18)
C2' C3' C4' 119.7(2)
O3' C4' C3' 120.7(2)
O3' C4' C5' 118.9(2)
C3' C4' C5' 120.4(2)
C6' C5' C4' 119.7(2)
C6' C5' H5'A 120.1
C4' C5' H5'A 120.1
C5' C6' C1' 120.8(2)
C5' C6' H6'A 119.6
C1' C6' H6'A 119.6
O4' C7' O5' 121.6(2)
O4' C7' C1' 122.3(2)
O5' C7' C1' 116.1(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1W H1WA 0.8200
O1 C2 1.365(3)
O1 H1A 0.8200
O2 C3 1.381(3)
O2 H2A 0.8200
O3 C4 1.355(2)
O3 H3A 0.8200
O4 C7 1.237(3)
O5 C7 1.317(3)
O5 H5B 0.8200
C1 C6 1.404(3)
C1 C2 1.407(3)
C1 C7 1.457(3)
C2 C3 1.384(3)
C3 C4 1.382(3)
C4 C5 1.391(3)
C5 C6 1.376(3)
C5 H5A 0.9300
C6 H6A 0.9300
O1' C2' 1.359(3)
O1' H1'A 0.8200
O2' C3' 1.371(3)
O2' H2'A 0.8200
O3' C4' 1.360(2)
O3' H3'A 0.8200
O4' C7' 1.243(3)
O5' C7' 1.314(3)
O5' H5'B 0.8200
C1' C2' 1.401(3)
C1' C6' 1.403(3)
C1' C7' 1.463(3)
C2' C3' 1.386(3)
C3' C4' 1.393(3)
C4' C5' 1.395(3)
C5' C6' 1.373(3)
C5' H5'A 0.9300
C6' H6'A 0.9300
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
O1W H1WA O2 . 0.82 2.19 2.963(2) 156 yes
O1W H1WA O2' . 0.82 2.58 2.987(3) 112 no
O1 H1A O4 . 0.82 1.88 2.587(3) 143 yes
O2 H2A O2' 1_556 0.82 2.05 2.839(4) 161 yes
O2 H2A O1 . 0.82 2.32 2.715(2) 111 no
O3 H3A O3' 2_656 0.82 2.06 2.828(3) 155 yes
O3 H3A O2 . 0.82 2.29 2.735(3) 115 no
O5 H5B O4' 4_554 0.82 1.88 2.679(4) 165 yes
O1' H1'A O4' . 0.82 1.87 2.588(3) 145 yes
O2' H2'A O1 . 0.82 1.95 2.729(4) 159 yes
O2' H2'A O1' . 0.82 2.32 2.716(2) 110 no
O3' H3'A O1W . 0.82 2.06 2.841(3) 158 yes
O3' H3'A O2' . 0.82 2.28 2.727(4) 115 no
O5' H5'B O4 4_454 0.82 1.85 2.659(4) 171 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
C6 C1 C2 O1 -178.9(2)
C7 C1 C2 O1 -0.8(3)
C6 C1 C2 C3 0.1(3)
C7 C1 C2 C3 178.2(2)
O1 C2 C3 O2 0.7(3)
C1 C2 C3 O2 -178.4(2)
O1 C2 C3 C4 179.6(2)
C1 C2 C3 C4 0.5(3)
O2 C3 C4 O3 -2.0(3)
C2 C3 C4 O3 179.0(2)
O2 C3 C4 C5 177.9(2)
C2 C3 C4 C5 -1.0(4)
O3 C4 C5 C6 -179.1(2)
C3 C4 C5 C6 1.0(4)
C4 C5 C6 C1 -0.4(4)
C2 C1 C6 C5 -0.1(4)
C7 C1 C6 C5 -178.2(2)
C6 C1 C7 O4 -179.6(2)
C2 C1 C7 O4 2.3(4)
C6 C1 C7 O5 1.0(3)
C2 C1 C7 O5 -177.1(2)
C6' C1' C2' O1' -178.2(2)
C7' C1' C2' O1' 4.6(4)
C6' C1' C2' C3' 2.1(4)
C7' C1' C2' C3' -175.1(2)
O1' C2' C3' O2' -0.9(3)
C1' C2' C3' O2' 178.8(2)
O1' C2' C3' C4' 179.3(2)
C1' C2' C3' C4' -1.0(4)
O2' C3' C4' O3' -0.8(3)
C2' C3' C4' O3' 179.0(2)
O2' C3' C4' C5' 179.7(2)
C2' C3' C4' C5' -0.5(4)
O3' C4' C5' C6' -178.6(2)
C3' C4' C5' C6' 0.9(4)
C4' C5' C6' C1' 0.3(4)
C2' C1' C6' C5' -1.8(4)
C7' C1' C6' C5' 175.3(2)
C2' C1' C7' O4' -1.2(4)
C6' C1' C7' O4' -178.3(2)
C2' C1' C7' O5' 177.7(2)
C6' C1' C7' O5' 0.6(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 28535870
