#------------------------------------------------------------------------------
#$Date: 2011-09-10 06:16:28 +0300 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2200756.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_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       \w-2\q
_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/[\s^2^(Fo^2^) + (0.1P)^2^] where P = (Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .175
_reflns_number_gt                1763
_reflns_number_total             3037
_reflns_threshold_expression     I>2\s(I)
_[local]_cod_data_source_file    tk6035.cif
_[local]_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_occupancy
_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_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 .0286(9) .0760(10) .0500(10) -.0069(8) .0162(8) .0223(9)
O2 .0335(9) .0680(10) .0443(10) -.0083(8) .0188(8) .0185(8)
O3 .0364(9) .0640(10) .0387(9) -.0054(8) .0152(7) .0219(8)
O4 .0306(9) .0760(10) .0425(10) .0023(9) .0163(8) .0260(9)
O5 .0480(10) .094(2) .0362(9) -.0050(10) .0222(8) .0289(10)
O6 .0420(10) .0660(10) .0350(9) -.0055(9) .0106(7) .0246(8)
O7 .0303(8) .0590(10) .0366(9) -.0011(7) .0152(7) .0192(8)
O8 .0373(9) .0880(10) .0295(8) -.0085(9) .0170(7) .0217(8)
C1 .0300(10) .0410(10) .0380(10) -.0091(9) .0140(9) .0065(10)
C2 .0320(10) .0380(10) .0300(10) -.0088(9) .0127(9) .0067(9)
C3 .0290(10) .0440(10) .0380(10) -.0070(10) .0138(9) .0096(10)
C4 .0400(10) .058(2) .0410(10) -.0080(10) .0220(10) .0130(10)
C5 .0400(10) .067(2) .0360(10) -.0080(10) .0120(10) .0190(10)
C6 .0310(10) .0520(10) .0430(10) -.0080(10) .0110(10) .0160(10)
C7 .0320(10) .0420(10) .0420(10) -.0093(10) .0160(10) .0070(10)
C8 .0350(10) .0420(10) .0245(10) -.0105(10) .0119(9) .0093(9)
C9 .0260(10) .0400(10) .0290(10) -.0095(9) .0107(8) .0081(9)
C10 .0300(10) .0490(10) .0280(10) -.0112(10) .0133(9) .0093(9)
C11 .0370(10) .068(2) .0290(10) -.0090(10) .0102(9) .0190(10)
C12 .0250(10) .072(2) .0360(10) -.0050(10) .0091(9) .0180(10)
C13 .0320(10) .057(2) .0340(10) -.0090(10) .0168(10) .0110(10)
C14 .0370(10) .0440(10) .0300(10) -.0071(10) .0155(9) .0118(9)
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_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