#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/54/2225434.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_2225434
loop_
_publ_author_name
'Hu, Tuoping'
_publ_section_title
;
 2,2'-[2,3,5,6-Tetramethyl-p-phenylenebis(methyleneoxy)]dibenzoic
 acid
;
_journal_coeditor_code           BQ2194
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o995
_journal_paper_doi               10.1107/S1600536810011220
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C26 H26 O6'
_chemical_formula_moiety         'C26 H26 O6'
_chemical_formula_sum            'C26 H26 O6'
_chemical_formula_weight         434.47
_chemical_name_systematic
;
2,2'-[2,3,5,6-Tetramethyl-p-phenylenebis(methyleneoxy)]dibenzoic acid
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 96.902(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.2841(16)
_cell_length_b                   8.6936(15)
_cell_length_c                   14.075(2)
_cell_measurement_reflns_used    1055
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.8
_cell_volume                     1127.8(3)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2007)'
_computing_data_collection       'SMART (Bruker, 2007)'
_computing_data_reduction        'SAINT-Plus (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 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker SMART 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  0.0325
_diffrn_reflns_av_sigmaI/netI    0.0441
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6437
_diffrn_reflns_theta_full        26.5
_diffrn_reflns_theta_max         27.5
_diffrn_reflns_theta_min         2.2
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.994
_exptl_absorpt_correction_T_min  0.985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             460
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.233
_refine_diff_density_min         -0.148
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     159
_refine_ls_number_reflns         2322
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.1003
_refine_ls_R_factor_gt           0.0499
_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)+(0.0659P)²+0.1641P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1263
_refine_ls_wR_factor_ref         0.1573
_reflns_number_gt                1269
_reflns_number_total             2322
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bq2194.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2225434
_cod_database_fobs_code          2225434
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_disorder_assembly
_atom_site_disorder_group
C C1 0.4303(2) 0.0417(3) 0.12146(17) 0.0593(6) Uani d . 1 . .
C C2 0.3798(2) 0.0589(3) 0.21720(15) 0.0552(6) Uani d . 1 A .
C C3 0.4391(3) -0.0387(3) 0.29015(17) 0.0711(7) Uani d . 1 . .
H H3 0.5065 -0.1123 0.2768 0.085 Uiso calc R 1 A .
C C4 0.4006(3) -0.0291(3) 0.38111(18) 0.0820(8) Uani d . 1 A .
H H4 0.4405 -0.0963 0.4286 0.098 Uiso calc R 1 . .
C C5 0.3027(3) 0.0805(3) 0.40112(17) 0.0775(8) Uani d . 1 . .
H H5 0.2774 0.0885 0.4629 0.093 Uiso calc R 1 A .
C C6 0.2413(3) 0.1787(3) 0.33116(17) 0.0666(7) Uani d . 1 A .
H H6 0.1750 0.2526 0.3459 0.080 Uiso calc R 1 . .
C C7 0.2781(2) 0.1680(3) 0.23858(15) 0.0558(6) Uani d . 1 . .
C C8 0.1090(3) 0.3686(3) 0.18341(18) 0.0764(8) Uani d . 1 . .
H H8A 0.1458 0.4480 0.2283 0.092 Uiso calc R 1 A .
H H8B 0.0318 0.3139 0.2097 0.092 Uiso calc R 1 . .
C C9 0.0536(3) 0.4386(3) 0.08832(18) 0.0666(7) Uani d . 1 A .
C C10 -0.0399(3) 0.3513(3) 0.0242(2) 0.0687(7) Uani d . 1 . .
C C11 -0.0835(3) 0.1899(3) 0.0519(2) 0.1008(10) Uani d . 1 A .
H H11A -0.1073 0.1293 -0.0048 0.151 Uiso calc R 1 . .
H H11B -0.1664 0.1959 0.0865 0.151 Uiso calc R 1 . .
H H11C -0.0043 0.1428 0.0916 0.151 Uiso calc R 1 . .
C C12 0.0955(2) 0.5869(3) 0.06413(19) 0.0687(7) Uani d . 1 . .
C C13 0.2028(3) 0.6782(4) 0.1319(2) 0.1005(10) Uani d . 1 A .
H H13A 0.2806 0.7135 0.0983 0.151 Uiso calc R 1 . .
H H13B 0.2412 0.6137 0.1843 0.151 Uiso calc R 1 . .
H H13C 0.1545 0.7649 0.1560 0.151 Uiso calc R 1 . .
O O1 0.3567(2) 0.0876(2) 0.04745(12) 0.0919(7) Uani d . 1 A .
O O2A 0.5605(9) -0.0059(16) 0.1171(6) 0.076(3) Uani d P 0.59(4) A 1
H H2A 0.5699 -0.0296 0.0618 0.114 Uiso calc PR 0.59(4) A 1
O O2B 0.524(3) -0.059(4) 0.1191(11) 0.130(6) Uani d P 0.41(4) A 2
H H2B 0.5576 -0.0543 0.0678 0.196 Uiso calc PR 0.41(4) A 2
O O3 0.22344(16) 0.26410(18) 0.16631(11) 0.0674(5) Uani d . 1 A .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O2B C1 O1 . . 121.6(9) ?
O1 C1 O2A . . 119.3(5) ?
O2B C1 C2 . . 113.3(7) ?
O1 C1 C2 . . 121.8(2) ?
O2A C1 C2 . . 118.4(4) ?
C3 C2 C7 . . 118.2(2) ?
C3 C2 C1 . . 117.9(2) ?
C7 C2 C1 . . 124.0(2) ?
C4 C3 C2 . . 121.8(2) ?
C4 C3 H3 . . 119.1 ?
C2 C3 H3 . . 119.1 ?
C5 C4 C3 . . 119.2(2) ?
C5 C4 H4 . . 120.4 ?
C3 C4 H4 . . 120.4 ?
C4 C5 C6 . . 120.9(2) ?
C4 C5 H5 . . 119.6 ?
C6 C5 H5 . . 119.6 ?
C5 C6 C7 . . 120.2(2) ?
C5 C6 H6 . . 119.9 ?
C7 C6 H6 . . 119.9 ?
O3 C7 C6 . . 123.1(2) ?
O3 C7 C2 . . 117.07(19) ?
C6 C7 C2 . . 119.8(2) ?
O3 C8 C9 . . 106.66(18) ?
O3 C8 H8A . . 110.4 ?
C9 C8 H8A . . 110.4 ?
O3 C8 H8B . . 110.4 ?
C9 C8 H8B . . 110.4 ?
H8A C8 H8B . . 108.6 ?
C10 C9 C12 . . 120.8(2) ?
C10 C9 C8 . . 118.3(2) ?
C12 C9 C8 . . 120.9(2) ?
C12 C10 C9 3_565 . 120.0(2) ?
C12 C10 C11 3_565 . 120.1(2) ?
C9 C10 C11 . . 119.8(2) ?
C10 C11 H11A . . 109.5 ?
C10 C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
C10 C11 H11C . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 109.5 ?
C10 C12 C9 3_565 . 119.2(2) ?
C10 C12 C13 3_565 . 120.2(3) ?
C9 C12 C13 . . 120.6(3) ?
C12 C13 H13A . . 109.5 ?
C12 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
C12 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?
C1 O2A H2A . . 109.5 ?
C1 O2B H2B . . 109.5 ?
C7 O3 C8 . . 118.47(17) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 O2B . 1.237(16) ?
C1 O1 . 1.241(3) ?
C1 O2A . 1.286(9) ?
C1 C2 . 1.487(3) ?
C2 C3 . 1.393(3) ?
C2 C7 . 1.397(3) ?
C3 C4 . 1.372(3) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.369(4) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.375(3) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.389(3) ?
C6 H6 . 0.9300 ?
C7 O3 . 1.366(3) ?
C8 O3 . 1.440(3) ?
C8 C9 . 1.503(3) ?
C8 H8A . 0.9700 ?
C8 H8B . 0.9700 ?
C9 C10 . 1.399(3) ?
C9 C12 . 1.401(3) ?
C10 C12 3_565 1.395(3) ?
C10 C11 . 1.524(4) ?
C11 H11A . 0.9600 ?
C11 H11B . 0.9600 ?
C11 H11C . 0.9600 ?
C12 C10 3_565 1.395(3) ?
C12 C13 . 1.518(4) ?
C13 H13A . 0.9600 ?
C13 H13B . 0.9600 ?
C13 H13C . 0.9600 ?
O2A H2A . 0.8200 ?
O2B H2B . 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
O2A H2A O1 3_655 0.82 1.83 2.624(9) 164.1
O2B H2B O1 3_655 0.82 1.91 2.721(16) 168.4
C5 H5 Cg1 2_444 0.93 2.80 3.356(5) 119.5
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
O2B C1 C2 C3 . . . . -2(2) ?
O1 C1 C2 C3 . . . . 158.1(2) ?
O2A C1 C2 C3 . . . . -30.0(8) ?
O2B C1 C2 C7 . . . . 178(2) ?
O1 C1 C2 C7 . . . . -22.7(4) ?
O2A C1 C2 C7 . . . . 149.2(8) ?
C7 C2 C3 C4 . . . . -0.4(4) ?
C1 C2 C3 C4 . . . . 178.9(2) ?
C2 C3 C4 C5 . . . . -0.8(4) ?
C3 C4 C5 C6 . . . . 1.0(4) ?
C4 C5 C6 C7 . . . . 0.0(4) ?
C5 C6 C7 O3 . . . . -178.6(2) ?
C5 C6 C7 C2 . . . . -1.3(3) ?
C3 C2 C7 O3 . . . . 178.9(2) ?
C1 C2 C7 O3 . . . . -0.3(3) ?
C3 C2 C7 C6 . . . . 1.4(3) ?
C1 C2 C7 C6 . . . . -177.8(2) ?
O3 C8 C9 C10 . . . . 78.2(3) ?
O3 C8 C9 C12 . . . . -101.3(2) ?
C12 C9 C10 C12 . . . 3_565 -1.6(4) ?
C8 C9 C10 C12 . . . 3_565 179.0(2) ?
C12 C9 C10 C11 . . . . 179.7(2) ?
C8 C9 C10 C11 . . . . 0.3(3) ?
C10 C9 C12 C10 . . . 3_565 1.5(4) ?
C8 C9 C12 C10 . . . 3_565 -179.0(2) ?
C10 C9 C12 C13 . . . . -177.0(2) ?
C8 C9 C12 C13 . . . . 2.5(3) ?
C6 C7 O3 C8 . . . . -8.1(3) ?
C2 C7 O3 C8 . . . . 174.5(2) ?
C9 C8 O3 C7 . . . . -170.4(2) ?
