#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/38/2213865.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_2213865
loop_
_publ_author_name
'Potts, Storm'
'Bredenkamp, Martin W.'
'Gertenbach, Jan-André'
_publ_section_title
;
 4,4'-Oxydibenzoic acid
;
_journal_coeditor_code           KP2104
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2887
_journal_page_last               o2887
_journal_paper_doi               10.1107/S1600536807020570
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C14 H10 O5'
_chemical_formula_moiety         'C14 H10 O5'
_chemical_formula_sum            'C14 H10 O5'
_chemical_formula_weight         258.22
_chemical_name_common            work
_chemical_name_systematic
;
4,4'-Oxydibenzoic acid
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                86.848(3)
_cell_angle_beta                 83.106(3)
_cell_angle_gamma                79.309(3)
_cell_formula_units_Z            2
_cell_length_a                   5.3654(9)
_cell_length_b                   6.4093(11)
_cell_length_c                   16.847(3)
_cell_measurement_reflns_used    2085
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.66
_cell_measurement_theta_min      2.44
_cell_volume                     564.85(17)
_computing_cell_refinement       'SAINT (Bruker, 2003)'
_computing_data_collection       'SMART (Bruker, 2002)'
_computing_data_reduction        SAINT
_computing_molecular_graphics
'X-SEED (Barbour, 2001; Atwood & Barbour, 2003)'
_computing_publication_material  'publCIF (Westrip, 2007)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.921
_diffrn_measurement_device_type  'Bruker APEX CCD area-detector'
_diffrn_measurement_method       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  0.0525
_diffrn_reflns_av_sigmaI/netI    0.0585
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            6444
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.27
_diffrn_reflns_theta_min         2.44
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.12
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.518
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             268
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.38
_refine_diff_density_min         -0.35
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.10
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2582
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.099
_refine_ls_R_factor_all          0.0703
_refine_ls_R_factor_gt           0.0449
_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)+(0.0549P)²+0.0103P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1081
_refine_ls_wR_factor_ref         0.1231
_reflns_number_gt                1901
_reflns_number_total             2582
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            kp2104.cif
_cod_data_source_block           I
_cod_original_cell_volume        564.86(16)
_cod_database_code               2213865
_cod_database_fobs_code          2213865
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
O O1 0.1763(2) 1.24541(18) 0.02374(7) 0.0251(3) Uani d . 1
H H1 0.0651 1.3129 -0.0037 0.030 Uiso calc R 1
C C1 0.2712(3) 1.3777(3) 0.06123(10) 0.0176(4) Uani d . 1
O O2 0.2019(2) 1.57409(18) 0.05702(7) 0.0242(3) Uani d . 1
C C2 0.4720(3) 1.2816(3) 0.11236(10) 0.0171(4) Uani d . 1
O O3 1.0046(2) 1.03887(17) 0.26827(7) 0.0196(3) Uani d . 1
C C3 0.5979(3) 1.4139(3) 0.14919(10) 0.0179(4) Uani d . 1
H H3 0.5621 1.5629 0.1385 0.022 Uiso calc R 1
O O4 1.1999(2) 0.12156(17) 0.43485(7) 0.0206(3) Uani d . 1
C C4 0.7753(3) 1.3304(3) 0.20139(10) 0.0187(4) Uani d . 1
H H4 0.8604 1.4211 0.2268 0.022 Uiso calc R 1
O O5 0.7865(2) 0.22879(18) 0.47782(7) 0.0219(3) Uani d . 1
H H5 0.8076 0.1086 0.5012 0.026 Uiso calc R 1
C C5 0.8262(3) 1.1128(3) 0.21581(10) 0.0166(4) Uani d . 1
C C6 0.7121(3) 0.9777(3) 0.17638(10) 0.0199(4) Uani d . 1
H H6 0.7564 0.8282 0.1845 0.024 Uiso calc R 1
C C7 0.5332(3) 1.0625(3) 0.12509(10) 0.0194(4) Uani d . 1
H H7 0.4522 0.9711 0.0986 0.023 Uiso calc R 1
C C8 0.9921(3) 0.8447(3) 0.30857(10) 0.0167(4) Uani d . 1
C C9 1.2095(3) 0.6890(3) 0.30130(10) 0.0186(4) Uani d . 1
H H9 1.3571 0.7134 0.2676 0.022 Uiso calc R 1
C C10 1.2098(3) 0.4977(3) 0.34358(10) 0.0185(4) Uani d . 1
H H10 1.3584 0.3903 0.3391 0.022 Uiso calc R 1
C C11 0.9941(3) 0.4623(2) 0.39243(9) 0.0155(4) Uani d . 1
C C12 0.7761(3) 0.6215(2) 0.39935(10) 0.0174(4) Uani d . 1
H H12 0.6280 0.5976 0.4329 0.021 Uiso calc R 1
C C13 0.7753(3) 0.8134(3) 0.35746(10) 0.0184(4) Uani d . 1
H H13 0.6280 0.9219 0.3622 0.022 Uiso calc R 1
C C14 0.9955(3) 0.2569(3) 0.43785(10) 0.0153(4) Uani d . 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
_geom_angle_publ_flag
C1 O1 H1 109.5 ?
O2 C1 O1 124.03(15) ?
O2 C1 C2 120.17(15) ?
O1 C1 C2 115.80(15) ?
C7 C2 C3 119.63(16) ?
C7 C2 C1 121.30(15) ?
C3 C2 C1 119.06(15) ?
C5 O3 C8 117.97(12) yes
C4 C3 C2 120.62(16) ?
C4 C3 H3 119.7 ?
C2 C3 H3 119.7 ?
C5 C4 C3 118.89(16) ?
C5 C4 H4 120.6 ?
C3 C4 H4 120.6 ?
C14 O5 H5 109.5 ?
O3 C5 C4 116.30(14) ?
O3 C5 C6 122.47(15) ?
C4 C5 C6 121.16(16) ?
C7 C6 C5 119.48(16) ?
C7 C6 H6 120.3 ?
C5 C6 H6 120.3 ?
C6 C7 C2 120.07(16) ?
C6 C7 H7 120.0 ?
C2 C7 H7 120.0 ?
C13 C8 C9 121.36(16) ?
C13 C8 O3 121.04(15) ?
C9 C8 O3 117.50(15) ?
C10 C9 C8 119.44(16) ?
C10 C9 H9 120.3 ?
C8 C9 H9 120.3 ?
C9 C10 C11 120.15(15) ?
C9 C10 H10 119.9 ?
C11 C10 H10 119.9 ?
C10 C11 C12 119.74(15) ?
C10 C11 C14 119.96(15) ?
C12 C11 C14 120.29(15) ?
C13 C12 C11 120.30(16) ?
C13 C12 H12 119.9 ?
C11 C12 H12 119.9 ?
C8 C13 C12 119.01(16) ?
C8 C13 H13 120.5 ?
C12 C13 H13 120.5 ?
O4 C14 O5 123.99(15) ?
O4 C14 C11 119.03(15) ?
O5 C14 C11 116.98(14) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.2933(19)
O1 H1 0.8400
C1 O2 1.2455(19)
C1 C2 1.484(2)
C2 C7 1.392(2)
C2 C3 1.390(2)
O3 C5 1.3820(19)
O3 C8 1.3930(19)
C3 C4 1.388(2)
C3 H3 0.9500
O4 C14 1.2633(19)
C4 C5 1.385(2)
C4 H4 0.9500
O5 C14 1.274(2)
O5 H5 0.8400
C5 C6 1.386(2)
C6 C7 1.385(2)
C6 H6 0.9500
C7 H7 0.9500
C8 C13 1.382(2)
C8 C9 1.385(2)
C9 C10 1.384(2)
C9 H9 0.9500
C10 C11 1.384(2)
C10 H10 0.9500
C11 C12 1.400(2)
C11 C14 1.485(2)
C12 C13 1.383(2)
C12 H12 0.9500
C13 H13 0.9500
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
O2 C1 C2 C7 172.85(16)
O1 C1 C2 C7 -6.4(2)
O2 C1 C2 C3 -6.1(2)
O1 C1 C2 C3 174.68(15)
C7 C2 C3 C4 -3.0(3)
C1 C2 C3 C4 175.93(15)
C2 C3 C4 C5 0.4(3)
C8 O3 C5 C4 155.32(15)
C8 O3 C5 C6 -27.7(2)
C3 C4 C5 O3 179.98(14)
C3 C4 C5 C6 3.0(3)
O3 C5 C6 C7 179.47(15)
C4 C5 C6 C7 -3.7(3)
C5 C6 C7 C2 1.1(3)
C3 C2 C7 C6 2.3(3)
C1 C2 C7 C6 -176.65(15)
C5 O3 C8 C13 -59.0(2)
C5 O3 C8 C9 124.55(16)
C13 C8 C9 C10 0.2(3)
O3 C8 C9 C10 176.70(14)
C8 C9 C10 C11 0.3(2)
C9 C10 C11 C12 -0.5(2)
C9 C10 C11 C14 -179.86(14)
C10 C11 C12 C13 0.2(2)
C14 C11 C12 C13 179.56(14)
C9 C8 C13 C12 -0.5(2)
O3 C8 C13 C12 -176.87(14)
C11 C12 C13 C8 0.3(2)
C10 C11 C14 O4 4.2(2)
C12 C11 C14 O4 -175.22(15)
C10 C11 C14 O5 -175.75(14)
C12 C11 C14 O5 4.9(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 67729
