#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/07/2200756.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_2200756
loop_
_publ_author_name
'Okabe, Nobuo'
'Kyoyama, Hasuyo'
_publ_section_title
;
 2,3-Dihydroxybenzoic acid
;
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1224
_journal_page_last               o1226
_journal_paper_doi               10.1107/S1600536801018682
_journal_volume                  57
_journal_year                    2001
_chemical_formula_iupac          'C7 H6 O4'
_chemical_formula_moiety         'C7 H6 O4'
_chemical_formula_sum            'C7 H6 O4'
_chemical_formula_weight         154.12
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_cell_angle_alpha                110.290(10)
_cell_angle_beta                 113.750(10)
_cell_angle_gamma                67.10(2)
_cell_formula_units_Z            4
_cell_length_a                   9.431(2)
_cell_length_b                   10.307(2)
_cell_length_c                   8.2910(10)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    296
_cell_measurement_theta_max      15.0
_cell_measurement_theta_min      14.3
_cell_volume                     662.0(2)
_computing_cell_refinement       'MSC/AFC Diffractometer Control Software'
_computing_data_collection
;
MSC/AFC Diffractometer Control Software (Molecular Structure Corporation &
Rigaku, 1999a)
;
_computing_data_reduction
'TEXSAN ((Molecular Structure Corporation & Rigaku, 1999b)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  TEXSAN
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution
'SIR88 (Burla et al., 1989) and 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       ω-2θ
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     .7107
_diffrn_reflns_av_R_equivalents  .020
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            3221
_diffrn_reflns_theta_full        27.5
_diffrn_reflns_theta_max         27.5
_diffrn_standards_decay_%        1.0
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    .129
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'light brown'
_exptl_crystal_density_diffrn    1.546
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             320
_exptl_crystal_size_max          .30
_exptl_crystal_size_mid          .20
_exptl_crystal_size_min          .10
_refine_diff_density_max         .26
_refine_diff_density_min         -.26
_refine_ls_extinction_coef       none
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.07
_refine_ls_hydrogen_treatment    noref
_refine_ls_number_parameters     199
_refine_ls_number_reflns         1763
_refine_ls_R_factor_gt           .044
_refine_ls_shift/su_max          <0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²) + (0.1P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .175
_reflns_number_gt                1763
_reflns_number_total             3037
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            tk6035.cif
_cod_data_source_block           I
_cod_database_code               2200756
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-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_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
O1 .0186(2) .5143(2) .2991(2) .0507(5) Uani d . 1.00 . . O
O2 .2021(2) .4296(2) .5401(2) .0468(5) Uani d . 1.00 . . O
O3 .5067(2) .3084(2) .5433(2) .0452(5) Uani d . 1.00 . . O
O4 .7254(2) .2519(2) .3772(2) .0502(5) Uani d . 1.00 . . O
O5 1.1566(2) .1113(2) -.3088(2) .0573(6) Uani d . 1.00 . . O
O6 .9101(2) .1966(2) -.2777(2) .0478(5) Uani d . 1.00 . . O
O7 .8820(2) .2281(2) .0372(2) .0417(4) Uani d . 1.00 . . O
O8 1.0278(2) .1671(2) .3654(2) .0500(5) Uani d . 1.00 . . O
C1 .2881(3) .4160(3) .3002(3) .0359(5) Uani d . 1.00 . . C
C2 .4500(3) .3474(2) .3829(3) .0330(5) Uani d . 1.00 . . C
C3 .5647(3) .3157(3) .2977(3) .0366(5) Uani d . 1.00 . . C
C4 .5190(3) .3485(3) .1332(3) .0444(6) Uani d . 1.00 . . C
C5 .3584(3) .4144(3) .0505(3) .0474(6) Uani d . 1.00 . . C
C6 .2432(3) .4484(3) .1325(3) .0421(6) Uani d . 1.00 . . C
C7 .1670(3) .4539(3) .3904(3) .0386(5) Uani d . 1.00 . . C
C8 1.1353(3) .1117(2) -.0369(3) .0327(5) Uani d . 1.00 . . C
C9 1.0423(2) .1556(2) .0786(3) .0307(5) Uani d . 1.00 . . C
C10 1.1170(3) .1240(3) .2497(3) .0339(5) Uani d . 1.00 . . C
C11 1.2781(3) .0504(3) .3034(3) .0441(6) Uani d . 1.00 . . C
C12 1.3695(3) .0070(3) .1889(3) .0457(6) Uani d . 1.00 . . C
C13 1.2987(3) .0377(3) .0198(3) .0396(5) Uani d . 1.00 . . C
C14 1.0555(3) .1442(3) -.2170(3) .0357(5) Uani d . 1.00 . . C
H1 -.0485 .5262 .3493 .0625 Uiso calc . 1.00 . . H
H2 .4119 .3396 .5836 .0625 Uiso calc . 1.00 . . H
H3 .7397 .2428 .4847 .0625 Uiso calc . 1.00 . . H
H4 .5950 .3253 .0766 .0513 Uiso calc . 1.00 . . H
H5 .3286 .4363 -.0591 .0552 Uiso calc . 1.00 . . H
H6 .1370 .4916 .0768 .0505 Uiso calc . 1.00 . . H
H7 1.1131 .1305 -.4106 .0625 Uiso calc . 1.00 . . H
H8 .8468 .2330 -.0687 .0612 Uiso calc . 1.00 . . H
H9 .9314 .1886 .3087 .0744 Uiso calc . 1.00 . . H
H10 1.3246 .0280 .4147 .0515 Uiso calc . 1.00 . . H
H11 1.4781 -.0420 .2260 .0539 Uiso calc . 1.00 . . H
H12 1.3615 .0102 -.0547 .0467 Uiso calc . 1.00 . . H
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
C7 O1 H1 1_555 1_555 111.9 no
C2 O3 H2 1_555 1_555 105.2 no
C3 O4 H3 1_555 1_555 109.8 no
C14 O5 H7 1_555 1_555 114.8 no
C9 O7 H8 1_555 1_555 109.4 no
C10 O8 H9 1_555 1_555 109.4 no
C2 C1 C6 1_555 1_555 119.7(3) yes
C2 C1 C7 1_555 1_555 119.6(2) yes
C6 C1 C7 1_555 1_555 120.7(2) yes
O3 C2 C1 1_555 1_555 124.7(3) yes
O3 C2 C3 1_555 1_555 116.3(2) yes
C1 C2 C3 1_555 1_555 119.0(2) yes
O4 C3 C2 1_555 1_555 120.6(2) yes
O4 C3 C4 1_555 1_555 118.7(3) yes
C2 C3 C4 1_555 1_555 120.7(2) yes
C3 C4 C5 1_555 1_555 120.2(3) yes
C3 C4 H4 1_555 1_555 120.2 no
C5 C4 H4 1_555 1_555 119.6 no
C4 C5 C6 1_555 1_555 120.3(3) yes
C4 C5 H5 1_555 1_555 119.8 no
C6 C5 H5 1_555 1_555 119.9 no
C1 C6 C5 1_555 1_555 120.1(2) yes
C1 C6 H6 1_555 1_555 119.9 no
C5 C6 H6 1_555 1_555 120.0 no
O1 C7 O2 1_555 1_555 122.7(3) yes
O1 C7 C1 1_555 1_555 114.6(2) yes
O2 C7 C1 1_555 1_555 122.7(2) yes
C9 C8 C13 1_555 1_555 119.7(2) yes
C9 C8 C14 1_555 1_555 118.5(2) yes
C13 C8 C14 1_555 1_555 121.8(2) yes
O7 C9 C8 1_555 1_555 124.7(2) yes
O7 C9 C10 1_555 1_555 116.5(2) yes
C8 C9 C10 1_555 1_555 118.8(2) yes
O8 C10 C9 1_555 1_555 119.6(2) yes
O8 C10 C11 1_555 1_555 119.6(2) yes
C9 C10 C11 1_555 1_555 120.8(2) yes
C10 C11 C12 1_555 1_555 120.2(2) yes
C10 C11 H10 1_555 1_555 119.7 no
C12 C11 H10 1_555 1_555 120.0 no
C11 C12 C13 1_555 1_555 120.0(2) yes
C11 C12 H11 1_555 1_555 119.9 no
C13 C12 H11 1_555 1_555 120.1 no
C8 C13 C12 1_555 1_555 120.4(3) yes
C8 C13 H12 1_555 1_555 120.3 no
C12 C13 H12 1_555 1_555 119.3 no
O5 C14 O6 1_555 1_555 122.6(2) yes
O5 C14 C8 1_555 1_555 113.8(2) yes
O6 C14 C8 1_555 1_555 123.6(3) yes
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 C7 . . 1.310(2) yes
O1 H1 . . .839 no
O2 C7 . . 1.238(4) yes
O3 C2 . . 1.359(3) yes
O3 H2 . . .978 no
O4 C3 . . 1.372(2) yes
O4 H3 . . .879 no
O5 C14 . . 1.325(4) yes
O5 H7 . . .833 no
O6 C14 . . 1.217(3) yes
O7 C9 . . 1.357(2) yes
O7 H8 . . .816 no
O8 C10 . . 1.375(3) yes
O8 H9 . . .817 no
C1 C2 . . 1.398(3) yes
C1 C6 . . 1.401(4) yes
C1 C7 . . 1.468(4) yes
C2 C3 . . 1.399(4) yes
C3 C4 . . 1.375(4) yes
C4 C5 . . 1.382(3) yes
C4 H4 . . .922 no
C5 C6 . . 1.378(4) yes
C5 H5 . . .918 no
C6 H6 . . .915 no
C8 C9 . . 1.399(4) yes
C8 C13 . . 1.389(3) yes
C8 C14 . . 1.468(3) yes
C9 C10 . . 1.397(3) yes
C10 C11 . . 1.369(3) yes
C11 C12 . . 1.382(4) yes
C11 H10 . . .916 no
C12 C13 . . 1.379(4) yes
C12 H11 . . .922 no
C13 H12 . . .924 no
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_2
O1 O2 2.685(3) 2_566
O1 O7 3.367(3) 1_455
O1 O6 3.374(4) 2_665
O1 C9 3.473(3) 1_455
O1 C6 3.485(3) 2_565
O1 O8 3.498(2) 2_666
O1 C7 3.521(4) 2_566
O1 O5 3.543(3) 2_665
O1 C14 3.564(4) 2_665
O1 C5 3.567(3) 2_565
O2 O8 3.309(3) 1_455
O2 O2 3.377(3) 2_566
O2 C10 3.393(3) 1_455
O2 O4 3.394(3) 2_666
O2 C7 3.431(3) 2_566
O3 O6 3.352(2) 1_556
O3 C3 3.513(3) 2_666
O3 C2 3.541(3) 2_666
O4 O6 2.809(2) 1_556
O4 C7 3.271(3) 2_666
O4 O5 3.372(3) 2_755
O4 C1 3.532(3) 2_666
O4 C13 3.592(3) 2_755
O5 O8 2.645(3) 1_554
O5 C10 3.571(3) 1_554
O6 C6 3.340(3) 2_665
O6 O8 3.415(3) 2_755
O6 O8 3.441(3) 1_554
O6 C10 3.504(4) 2_755
O6 C11 3.537(4) 2_755
O7 C13 3.567(4) 2_755
O7 C8 3.569(4) 2_755
O7 C12 3.572(4) 2_755
O7 C9 3.577(3) 2_755
O7 C11 3.580(3) 2_755
O7 C10 3.583(3) 2_755
O8 C14 3.297(4) 2_755
O8 C14 3.450(3) 1_556
O8 C8 3.561(3) 2_755
O8 C7 3.589(4) 1_655
C2 C2 3.339(5) 2_666
C2 C3 3.554(3) 2_666
C2 C12 3.557(4) 1_455
C7 C10 3.346(4) 1_455
C7 C9 3.518(3) 1_455
C8 C10 3.581(4) 2_755
C9 C9 3.298(5) 2_755
C9 C10 3.551(3) 2_755
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
O4 H3 O3 1_555 .88 2.24 2.700(3) 113 yes
O3 H2 O2 1_555 .98 1.77 2.642(2) 147 yes
O8 H9 O7 1_555 .82 2.26 2.682(2) 113 yes
O7 H8 O6 1_555 .82 1.93 2.625(2) 143 yes
O1 H1 O2 2_566 .84 1.85 2.685(3) 175 yes
O5 H7 O8 1_554 .83 1.81 2.645(2) 177 yes
O4 H3 O6 1_556 .88 2.05 2.809(2) 144 yes
O8 H9 O4 1_555 .82 2.04 2.670(2) 134 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 C7 C1 C2 1_555 1_555 1_555 1_555 -178.3(2) yes
O1 C7 C1 C6 1_555 1_555 1_555 1_555 2.0(4) yes
O2 C7 C1 C2 1_555 1_555 1_555 1_555 1.1(4) yes
O2 C7 C1 C6 1_555 1_555 1_555 1_555 -178.6(3) yes
O3 C2 C1 C6 1_555 1_555 1_555 1_555 -178.7(2) yes
O3 C2 C1 C7 1_555 1_555 1_555 1_555 1.6(4) yes
O3 C2 C3 O4 1_555 1_555 1_555 1_555 -1.6(3) yes
O3 C2 C3 C4 1_555 1_555 1_555 1_555 178.8(2) yes
O4 C3 C2 C1 1_555 1_555 1_555 1_555 178.3(2) yes
O4 C3 C4 C5 1_555 1_555 1_555 1_555 -179.2(2) yes
O5 C14 C8 C9 1_555 1_555 1_555 1_555 173.6(2) yes
O5 C14 C8 C13 1_555 1_555 1_555 1_555 -7.2(4) yes
O6 C14 C8 C9 1_555 1_555 1_555 1_555 -6.3(4) yes
O6 C14 C8 C13 1_555 1_555 1_555 1_555 172.9(3) yes
O7 C9 C8 C13 1_555 1_555 1_555 1_555 -179.9(2) yes
O7 C9 C8 C14 1_555 1_555 1_555 1_555 -.7(4) yes
O7 C9 C10 O8 1_555 1_555 1_555 1_555 -.3(4) yes
O7 C9 C10 C11 1_555 1_555 1_555 1_555 179.6(2) yes
O8 C10 C9 C8 1_555 1_555 1_555 1_555 179.6(2) yes
O8 C10 C11 C12 1_555 1_555 1_555 1_555 -179.7(3) yes
C1 C2 C3 C4 1_555 1_555 1_555 1_555 -1.3(4) yes
C1 C6 C5 C4 1_555 1_555 1_555 1_555 -.2(4) yes
C2 C1 C6 C5 1_555 1_555 1_555 1_555 -.7(4) yes
C2 C3 C4 C5 1_555 1_555 1_555 1_555 .4(4) yes
C3 C2 C1 C6 1_555 1_555 1_555 1_555 1.5(4) yes
C3 C2 C1 C7 1_555 1_555 1_555 1_555 -178.2(2) yes
C3 C4 C5 C6 1_555 1_555 1_555 1_555 .4(4) yes
C5 C6 C1 C7 1_555 1_555 1_555 1_555 179.0(3) yes
C8 C9 C10 C11 1_555 1_555 1_555 1_555 -.5(4) yes
C8 C13 C12 C11 1_555 1_555 1_555 1_555 -.3(4) yes
C9 C8 C13 C12 1_555 1_555 1_555 1_555 .1(4) yes
C9 C10 C11 C12 1_555 1_555 1_555 1_555 .4(4) yes
C10 C9 C8 C13 1_555 1_555 1_555 1_555 .3(4) yes
C10 C9 C8 C14 1_555 1_555 1_555 1_555 179.5(2) yes
C10 C11 C12 C13 1_555 1_555 1_555 1_555 .0(5) yes
C12 C13 C8 C14 1_555 1_555 1_555 1_555 -179.1(3) yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 18
