#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/60/2206002.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_2206002
loop_
_publ_author_name
'Li, Yang'
'Ge, Feng-Yan'
'Chen, Li-Gong'
'Dong, Chuan-Ming'
'Yan, Xi-Long'
'Duan, Er-Hong'
'Zeng, Tao'
'Zhang, Yue-Cheng'
'Bai, Guo-Yi'
_publ_section_title
;
 2-(2,4-Dihydroxybenzoyl)benzoic acid
;
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1769
_journal_page_last               o1770
_journal_paper_doi               10.1107/S1600536805014844
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C14 H10 O5'
_chemical_formula_moiety         'C14 H10 O5'
_chemical_formula_sum            'C14 H10 O5'
_chemical_formula_weight         258.22
_chemical_melting_point          474
_chemical_name_systematic
;
2-(2,4-Dihydroxybenzoyl)benzoic acid
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 116.034(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.331(3)
_cell_length_b                   11.628(4)
_cell_length_c                   11.640(4)
_cell_measurement_reflns_used    2633
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      26.49
_cell_measurement_theta_min      2.62
_cell_volume                     1256.4(7)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        'SAINT (Bruker, 1997)'
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker SMART CCD'
_diffrn_measurement_method       'φ and ω'
_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  0.0994
_diffrn_reflns_av_sigmaI/netI    0.0675
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6755
_diffrn_reflns_theta_full        26.66
_diffrn_reflns_theta_max         26.66
_diffrn_reflns_theta_min         2.20
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  0.977
_exptl_absorpt_correction_T_min  0.963
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.212
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         2626
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0785
_refine_ls_R_factor_gt           0.0485
_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)+(0.0478P)²+0.3516P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1225
_refine_ls_wR_factor_ref         0.1459
_reflns_number_gt                1762
_reflns_number_total             2626
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh6413.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2206002
_cod_database_fobs_code          2206002
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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_type_symbol
O1 0.28344(15) 0.31036(16) 0.44868(15) 0.0581(5) Uani d . 1 O
O2 0.51504(16) 0.2925(2) 0.49583(19) 0.0746(6) Uani d . 1 O
H2 0.516(3) 0.250(3) 0.560(3) 0.087(10) Uiso d . 1 H
O3 0.01604(15) 0.33945(15) 0.18108(15) 0.0572(5) Uani d . 1 O
O4 -0.17529(15) 0.41733(17) 0.25016(16) 0.0608(5) Uani d . 1 O
H4 -0.134(3) 0.369(3) 0.216(3) 0.088(10) Uiso d . 1 H
O5 -0.0508(2) 0.75316(16) 0.5080(2) 0.0746(6) Uani d . 1 O
H5 -0.132(4) 0.733(3) 0.511(3) 0.103(11) Uiso d . 1 H
C1 0.3836(2) 0.32926(19) 0.42363(19) 0.0426(5) Uani d . 1 C
C2 0.3694(2) 0.39474(18) 0.30884(18) 0.0400(5) Uani d . 1 C
C3 0.23439(19) 0.43702(18) 0.22257(17) 0.0388(5) Uani d . 1 C
C4 0.2224(2) 0.4955(2) 0.1141(2) 0.0516(6) Uani d . 1 C
H4A 0.1331 0.5235 0.0563 0.062 Uiso calc R 1 H
C5 0.3419(2) 0.5127(2) 0.0909(2) 0.0547(6) Uani d . 1 C
H5A 0.3322 0.5515 0.0177 0.066 Uiso calc R 1 H
C6 0.4747(2) 0.4722(2) 0.1764(2) 0.0556(6) Uani d . 1 C
H6 0.5550 0.4846 0.1616 0.067 Uiso calc R 1 H
C7 0.4888(2) 0.4131(2) 0.2845(2) 0.0499(6) Uani d . 1 C
H7 0.5786 0.3853 0.3415 0.060 Uiso calc R 1 H
C8 0.09718(19) 0.42241(18) 0.23772(18) 0.0401(5) Uani d . 1 C
C9 0.05604(18) 0.50795(18) 0.30447(18) 0.0393(5) Uani d . 1 C
C10 -0.07981(19) 0.50272(19) 0.30834(19) 0.0433(5) Uani d . 1 C
C11 -0.1173(2) 0.5859(2) 0.3735(2) 0.0498(6) Uani d . 1 C
H11 -0.2072 0.5832 0.3736 0.060 Uiso calc R 1 H
C12 -0.0219(2) 0.67262(19) 0.4384(2) 0.0517(6) Uani d . 1 C
C13 0.1129(2) 0.6803(2) 0.4358(2) 0.0539(6) Uani d . 1 C
H13 0.1765 0.7395 0.4784 0.065 Uiso calc R 1 H
C14 0.1485(2) 0.59974(19) 0.3700(2) 0.0458(5) Uani d . 1 C
H14 0.2373 0.6053 0.3681 0.055 Uiso calc R 1 H
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
_geom_angle_publ_flag
C1 O2 H2 110(2) ?
C10 O4 H4 107(2) ?
C12 O5 H5 107(2) ?
O1 C1 O2 122.6(2) yes
O1 C1 C2 123.41(18) ?
O2 C1 C2 114.02(17) ?
C7 C2 C3 119.36(18) ?
C7 C2 C1 120.81(18) ?
C3 C2 C1 119.83(17) ?
C4 C3 C2 119.06(17) ?
C4 C3 C8 116.49(17) yes
C2 C3 C8 124.45(17) yes
C5 C4 C3 120.96(19) ?
C5 C4 H4A 119.5 ?
C3 C4 H4A 119.5 ?
C6 C5 C4 119.9(2) ?
C6 C5 H5A 120.1 ?
C4 C5 H5A 120.1 ?
C5 C6 C7 120.08(19) ?
C5 C6 H6 120.0 ?
C7 C6 H6 120.0 ?
C6 C7 C2 120.66(19) ?
C6 C7 H7 119.7 ?
C2 C7 H7 119.7 ?
O3 C8 C9 121.81(17) yes
O3 C8 C3 117.90(17) ?
C9 C8 C3 120.01(17) ?
C14 C9 C10 117.20(18) ?
C14 C9 C8 121.67(17) yes
C10 C9 C8 121.12(18) yes
O4 C10 C11 117.94(17) ?
O4 C10 C9 121.81(19) ?
C11 C10 C9 120.24(19) ?
C12 C11 C10 120.34(18) ?
C12 C11 H11 119.8 ?
C10 C11 H11 119.8 ?
O5 C12 C11 122.7(2) ?
O5 C12 C13 116.6(2) ?
C11 C12 C13 120.7(2) ?
C14 C13 C12 118.8(2) ?
C14 C13 H13 120.6 ?
C12 C13 H13 120.6 ?
C13 C14 C9 122.67(19) ?
C13 C14 H14 118.7 ?
C9 C14 H14 118.7 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C1 1.212(2) ?
O2 C1 1.316(2) yes
O2 H2 0.89(3) ?
O3 C8 1.258(2) ?
O4 C10 1.353(3) yes
O4 H4 0.90(3) ?
O5 C12 1.355(3) ?
O5 H5 0.89(4) ?
C1 C2 1.488(3) yes
C2 C7 1.398(3) ?
C2 C3 1.402(3) ?
C3 C4 1.391(3) ?
C3 C8 1.513(3) yes
C4 C5 1.389(3) ?
C4 H4A 0.9300 ?
C5 C6 1.377(3) ?
C5 H5A 0.9300 ?
C6 C7 1.384(3) ?
C6 H6 0.9300 ?
C7 H7 0.9300 ?
C8 C9 1.436(3) yes
C9 C14 1.412(3) ?
C9 C10 1.425(3) ?
C10 C11 1.385(3) ?
C11 C12 1.381(3) ?
C11 H11 0.9300 ?
C12 C13 1.409(3) ?
C13 C14 1.359(3) ?
C13 H13 0.9300 ?
C14 H14 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
O2 H2 O3 4_666 0.89(3) 1.76(3) 2.643(2) 177(3)
O4 H4 O3 . 0.90(3) 1.80(3) 2.602(2) 148(3)
O5 H5 O1 3_566 0.89(4) 1.89(4) 2.764(2) 169(3)
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
_geom_torsion_publ_flag
O1 C1 C2 C7 -179.5(2) yes
O2 C1 C2 C7 0.0(3) yes
O1 C1 C2 C3 -0.7(3) yes
O2 C1 C2 C3 178.9(2) yes
C7 C2 C3 C4 0.5(3) ?
C1 C2 C3 C4 -178.38(19) ?
C7 C2 C3 C8 179.7(2) ?
C1 C2 C3 C8 0.8(3) ?
C2 C3 C4 C5 -0.3(3) ?
C8 C3 C4 C5 -179.5(2) ?
C3 C4 C5 C6 -0.5(4) ?
C4 C5 C6 C7 0.9(4) ?
C5 C6 C7 C2 -0.6(4) ?
C3 C2 C7 C6 -0.1(3) ?
C1 C2 C7 C6 178.8(2) ?
C4 C3 C8 O3 84.0(3) ?
C2 C3 C8 O3 -95.2(2) ?
C4 C3 C8 C9 -90.0(2) ?
C2 C3 C8 C9 90.8(3) ?
O3 C8 C9 C14 178.77(19) yes
C3 C8 C9 C14 -7.5(3) ?
O3 C8 C9 C10 -0.5(3) yes
C3 C8 C9 C10 173.21(17) ?
C14 C9 C10 O4 -179.06(18) ?
C8 C9 C10 O4 0.3(3) ?
C14 C9 C10 C11 0.5(3) ?
C8 C9 C10 C11 179.82(19) ?
O4 C10 C11 C12 177.71(19) ?
C9 C10 C11 C12 -1.9(3) ?
C10 C11 C12 O5 -177.2(2) ?
C10 C11 C12 C13 2.1(3) ?
O5 C12 C13 C14 178.3(2) ?
C11 C12 C13 C14 -1.0(3) ?
C12 C13 C14 C9 -0.4(3) ?
C10 C9 C14 C13 0.6(3) ?
C8 C9 C14 C13 -178.7(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 195932
