#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/31/2233118.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_2233118
loop_
_publ_author_name
'Zhao, Ningning'
'Li, Wenjun'
'Chang, Zhidong'
'Sun, Changyan'
'Fan, Hongxia'
_publ_section_title
;
 3,3'-[Biphenyl-4,4'-diylbis(oxy)]diphthalic acid
;
_journal_coeditor_code           CV5208
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o211
_journal_paper_doi               10.1107/S1600536811053219
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C28 H18 O10'
_chemical_formula_moiety         'C28 H18 O10'
_chemical_formula_sum            'C28 H18 O10'
_chemical_formula_weight         514.42
_chemical_name_systematic
;
3,3'-[Biphenyl-4,4'-diylbis(oxy)]diphthalic acid
;
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_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            4
_cell_length_a                   21.5817(7)
_cell_length_b                   11.2676(4)
_cell_length_c                   9.5025(3)
_cell_measurement_reflns_used    1882
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.0461
_cell_measurement_theta_min      2.9528
_cell_volume                     2310.76(13)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0238
_diffrn_reflns_av_sigmaI/netI    0.0310
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            5587
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.96
_exptl_absorpt_coefficient_mu    0.114
_exptl_absorpt_correction_T_max  0.9688
_exptl_absorpt_correction_T_min  0.9569
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.479
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1064
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.179
_refine_diff_density_min         -0.160
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     343
_refine_ls_number_reflns         2857
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.0617
_refine_ls_R_factor_gt           0.0478
_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)+(0.0626P)²+0.1818P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1109
_refine_ls_wR_factor_ref         0.1175
_reflns_number_gt                2352
_reflns_number_total             2857
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            cv5208.cif
_cod_data_source_block           I
_cod_database_code               2233118
_cod_database_fobs_code          2233118
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'
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
C C1 0.30406(19) 1.3782(3) 1.6071(4) 0.0542(10) Uani d . 1 1
C C2 0.41811(18) 1.3386(3) 1.4287(4) 0.0450(9) Uani d . 1 1
C C3 0.30093(19) 1.3259(3) 1.4624(4) 0.0527(10) Uani d . 1 1
C C4 0.35348(17) 1.3116(3) 1.3805(4) 0.0445(9) Uani d . 1 1
C C5 0.34704(19) 1.2629(3) 1.2462(4) 0.0515(10) Uani d . 1 1
C C6 0.2897(2) 1.2302(4) 1.1958(5) 0.0638(12) Uani d . 1 1
H H6 0.2860 1.1980 1.1061 0.077 Uiso calc R 1 1
C C7 0.2378(2) 1.2454(4) 1.2786(5) 0.0691(13) Uani d . 1 1
H H7 0.1990 1.2236 1.2444 0.083 Uiso calc R 1 1
C C8 0.2431(2) 1.2924(4) 1.4110(5) 0.0609(11) Uani d . 1 1
H H8 0.2081 1.3020 1.4667 0.073 Uiso calc R 1 1
C C9 0.40425(18) 1.1761(4) 1.0552(4) 0.0509(10) Uani d . 1 1
C C10 0.3961(2) 1.0575(4) 1.0751(4) 0.0666(13) Uani d . 1 1
H H10 0.3870 1.0279 1.1641 0.080 Uiso calc R 1 1
C C11 0.4016(2) 0.9812(3) 0.9611(5) 0.0609(12) Uani d . 1 1
H H11 0.3963 0.9001 0.9749 0.073 Uiso calc R 1 1
C C12 0.41474(16) 1.0225(3) 0.8286(4) 0.0446(9) Uani d . 1 1
C C13 0.4236(2) 1.1432(3) 0.8129(5) 0.0589(11) Uani d . 1 1
H H13 0.4335 1.1738 0.7248 0.071 Uiso calc R 1 1
C C14 0.4178(2) 1.2195(3) 0.9266(5) 0.0596(11) Uani d . 1 1
H H14 0.4233 1.3007 0.9142 0.071 Uiso calc R 1 1
C C15 0.41748(16) 0.9389(3) 0.7056(4) 0.0438(9) Uani d . 1 1
C C16 0.4346(2) 0.8221(3) 0.7200(4) 0.0616(11) Uani d . 1 1
H H16 0.4469 0.7950 0.8082 0.074 Uiso calc R 1 1
C C17 0.4343(2) 0.7437(4) 0.6092(5) 0.0624(11) Uani d . 1 1
H H17 0.4464 0.6653 0.6227 0.075 Uiso calc R 1 1
C C18 0.41619(17) 0.7812(3) 0.4798(4) 0.0467(9) Uani d . 1 1
C C19 0.3990(2) 0.8959(3) 0.4610(5) 0.0639(12) Uani d . 1 1
H H19 0.3865 0.9217 0.3724 0.077 Uiso calc R 1 1
C C20 0.3997(2) 0.9744(3) 0.5721(4) 0.0606(12) Uani d . 1 1
H H20 0.3881 1.0529 0.5571 0.073 Uiso calc R 1 1
C C21 0.42764(16) 0.6151(3) 0.1051(4) 0.0410(8) Uani d . 1 1
C C22 0.3124(2) 0.5020(3) -0.0191(4) 0.0539(10) Uani d . 1 1
C C23 0.31384(17) 0.5530(3) 0.1252(4) 0.0458(9) Uani d . 1 1
C C24 0.36704(17) 0.6045(3) 0.1821(4) 0.0421(8) Uani d . 1 1
C C25 0.36412(17) 0.6571(3) 0.3145(4) 0.0466(9) Uani d . 1 1
C C26 0.30915(18) 0.6577(4) 0.3882(4) 0.0587(11) Uani d . 1 1
H H26 0.3074 0.6929 0.4767 0.070 Uiso calc R 1 1
C C27 0.25716(19) 0.6067(4) 0.3322(5) 0.0656(12) Uani d . 1 1
H H27 0.2202 0.6080 0.3824 0.079 Uiso calc R 1 1
C C28 0.2594(2) 0.5534(4) 0.2014(4) 0.0598(11) Uani d . 1 1
H H28 0.2241 0.5177 0.1646 0.072 Uiso calc R 1 1
O O1 0.35545(15) 1.4066(3) 1.6566(3) 0.0855(10) Uani d . 1 1
O O2 0.25406(16) 1.3930(3) 1.6720(3) 0.0896(11) Uani d . 1 1
H H2 0.2612 1.4218 1.7496 0.134 Uiso calc R 1 1
O O3 0.44618(13) 1.2493(2) 1.4775(4) 0.0628(8) Uani d . 1 1
H H3 0.4811 1.2688 1.5023 0.094 Uiso calc R 1 1
O O4 0.43977(14) 1.4384(2) 1.4219(4) 0.0752(10) Uani d . 1 1
O O5 0.46202(13) 0.5243(2) 0.0978(4) 0.0697(9) Uani d . 1 1
H H5 0.4936 0.5406 0.0537 0.105 Uiso calc R 1 1
O O6 0.44146(14) 0.7116(2) 0.0561(4) 0.0679(9) Uani d . 1 1
O O7 0.26478(17) 0.4490(3) -0.0584(4) 0.0890(11) Uani d . 1 1
O O8 0.35855(15) 0.5180(3) -0.0969(3) 0.0740(9) Uani d . 1 1
H H8A 0.3525 0.4863 -0.1733 0.111 Uiso calc R 1 1
O O9 0.40081(14) 1.2559(3) 1.1684(3) 0.0626(8) Uani d . 1 1
O O10 0.41860(12) 0.7034(2) 0.3652(3) 0.0551(7) 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
O1 C1 O2 123.1(4)
O1 C1 C3 119.2(4)
O2 C1 C3 117.7(4)
O4 C2 O3 124.7(4)
O4 C2 C4 121.8(3)
O3 C2 C4 113.4(3)
C4 C3 C8 120.3(4)
C4 C3 C1 121.7(4)
C8 C3 C1 118.0(4)
C3 C4 C5 118.6(4)
C3 C4 C2 124.5(3)
C5 C4 C2 116.8(3)
C6 C5 O9 123.7(4)
C6 C5 C4 120.8(4)
O9 C5 C4 115.4(3)
C5 C6 C7 119.9(4)
C5 C6 H6 120.1
C7 C6 H6 120.1
C8 C7 C6 120.2(4)
C8 C7 H7 119.9
C6 C7 H7 119.9
C7 C8 C3 120.2(4)
C7 C8 H8 119.9
C3 C8 H8 119.9
C14 C9 C10 120.6(4)
C14 C9 O9 118.3(3)
C10 C9 O9 121.0(4)
C9 C10 C11 119.3(4)
C9 C10 H10 120.4
C11 C10 H10 120.4
C12 C11 C10 121.6(3)
C12 C11 H11 119.2
C10 C11 H11 119.2
C11 C12 C13 117.5(3)
C11 C12 C15 120.6(3)
C13 C12 C15 121.8(3)
C12 C13 C14 120.9(4)
C12 C13 H13 119.6
C14 C13 H13 119.6
C9 C14 C13 120.1(3)
C9 C14 H14 120.0
C13 C14 H14 120.0
C16 C15 C20 116.3(3)
C16 C15 C12 122.2(3)
C20 C15 C12 121.4(3)
C15 C16 C17 122.5(4)
C15 C16 H16 118.8
C17 C16 H16 118.8
C18 C17 C16 119.7(4)
C18 C17 H17 120.1
C16 C17 H17 120.1
C17 C18 C19 119.6(4)
C17 C18 O10 120.0(3)
C19 C18 O10 120.3(4)
C18 C19 C20 120.5(4)
C18 C19 H19 119.7
C20 C19 H19 119.7
C19 C20 C15 121.3(4)
C19 C20 H20 119.3
C15 C20 H20 119.3
O6 C21 O5 123.8(3)
O6 C21 C24 118.0(3)
O5 C21 C24 118.2(3)
O7 C22 O8 123.2(4)
O7 C22 C23 118.6(4)
O8 C22 C23 118.2(4)
C28 C23 C24 119.7(3)
C28 C23 C22 117.9(4)
C24 C23 C22 122.3(3)
C25 C24 C23 119.3(3)
C25 C24 C21 116.4(3)
C23 C24 C21 124.1(3)
O10 C25 C26 123.9(3)
O10 C25 C24 116.1(3)
C26 C25 C24 120.0(3)
C27 C26 C25 120.4(4)
C27 C26 H26 119.8
C25 C26 H26 119.8
C26 C27 C28 120.2(4)
C26 C27 H27 119.9
C28 C27 H27 119.9
C23 C28 C27 120.3(4)
C23 C28 H28 119.9
C27 C28 H28 119.9
C1 O2 H2 109.5
C2 O3 H3 109.5
C21 O5 H5 109.5
C22 O8 H8A 109.5
C5 O9 C9 119.5(3)
C25 O10 C18 118.6(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O1 1.246(5)
C1 O2 1.254(5)
C1 C3 1.497(6)
C2 O4 1.219(4)
C2 O3 1.263(4)
C2 C4 1.499(5)
C3 C4 1.385(5)
C3 C8 1.392(5)
C4 C5 1.396(5)
C5 C6 1.377(6)
C5 O9 1.378(5)
C6 C7 1.381(6)
C6 H6 0.9300
C7 C8 1.370(6)
C7 H7 0.9300
C8 H8 0.9300
C9 C14 1.349(6)
C9 C10 1.361(6)
C9 O9 1.404(4)
C10 C11 1.388(6)
C10 H10 0.9300
C11 C12 1.372(6)
C11 H11 0.9300
C12 C13 1.382(5)
C12 C15 1.503(5)
C13 C14 1.386(5)
C13 H13 0.9300
C14 H14 0.9300
C15 C16 1.374(5)
C15 C20 1.384(6)
C16 C17 1.375(6)
C16 H16 0.9300
C17 C18 1.357(6)
C17 H17 0.9300
C18 C19 1.357(5)
C18 O10 1.399(4)
C19 C20 1.378(6)
C19 H19 0.9300
C20 H20 0.9300
C21 O6 1.220(4)
C21 O5 1.266(4)
C21 C24 1.504(5)
C22 O7 1.246(5)
C22 O8 1.253(5)
C22 C23 1.487(5)
C23 C28 1.380(5)
C23 C24 1.395(5)
C24 C25 1.392(5)
C25 O10 1.373(4)
C25 C26 1.378(5)
C26 C27 1.368(6)
C26 H26 0.9300
C27 C28 1.381(6)
C27 H27 0.9300
C28 H28 0.9300
O2 H2 0.8200
O3 H3 0.8200
O5 H5 0.8200
O8 H8A 0.8200
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 O7 1_567 0.82 1.85 2.649(4) 163.6
O8 H8A O1 1_543 0.82 1.85 2.659(4) 168.5
O3 H3 O6 2_676 0.82 1.76 2.575(4) 171.6
O5 H5 O4 2_673 0.82 1.92 2.732(4) 169.0
C11 H11 O6 1_556 0.93 2.46 3.284(5) 147.5
C13 H13 O3 1_554 0.93 2.51 3.438(6) 172.5
C16 H16 O6 1_556 0.93 2.54 3.431(6) 160.7
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 13706732
