#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/28/2232897.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_2232897
loop_
_publ_author_name
'Al-Mohammed, Nassir N.'
'Alias, Yatimah'
'Abdullah, Zanariah'
'Khaledi, Hamid'
_publ_section_title
;
 1,1'-{[1,4-Phenylenebis(methylene)]bis(oxy)bis(4,1-phenylene)}diethanone
;
_journal_coeditor_code           PV2469
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3164
_journal_paper_doi               10.1107/S160053681104565X
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C24 H22 O4'
_chemical_formula_moiety         'C24 H22 O4'
_chemical_formula_sum            'C24 H22 O4'
_chemical_formula_weight         374.42
_chemical_name_systematic
;
1,1'-{[1,4-Phenylenebis(methylene)]bis(oxy)bis(4,1-phenylene)}diethanone
;
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                116.164(5)
_cell_angle_beta                 106.328(7)
_cell_angle_gamma                100.196(7)
_cell_formula_units_Z            1
_cell_length_a                   8.1286(12)
_cell_length_b                   8.1610(7)
_cell_length_c                   8.4878(6)
_cell_measurement_reflns_used    1506
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.80
_cell_measurement_theta_min      2.93
_cell_volume                     454.41(10)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'X-SEED (Barbour, 2001)'
_computing_publication_material
'SHELXL97 (Sheldrick, 2008) and publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω 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  0.0195
_diffrn_reflns_av_sigmaI/netI    0.0342
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            2732
_diffrn_reflns_theta_full        25.49
_diffrn_reflns_theta_max         25.49
_diffrn_reflns_theta_min         2.79
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.9917
_exptl_absorpt_correction_T_min  0.9791
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.368
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             198
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.204
_refine_diff_density_min         -0.341
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         1654
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0443
_refine_ls_R_factor_gt           0.0404
_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)+(0.0644P)²+0.0983P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1085
_refine_ls_wR_factor_ref         0.1123
_reflns_number_gt                1472
_reflns_number_total             1654
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            pv2469.cif
_cod_data_source_block           I
_cod_original_cell_volume        454.41(8)
_cod_database_code               2232897
_cod_database_fobs_code          2232897
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
_atom_site_symmetry_multiplicity
O O1 1.00611(13) 1.92652(14) 1.27797(14) 0.0228(3) Uani d . 1 1
O O2 0.62238(13) 1.01503(13) 0.83520(13) 0.0192(3) Uani d . 1 1
C C1 1.22612(19) 1.8825(2) 1.4939(2) 0.0246(3) Uani d . 1 1
H H1A 1.2907 2.0214 1.5498 0.037 Uiso calc R 1 1
H H1B 1.3039 1.8086 1.4524 0.037 Uiso calc R 1 1
H H1C 1.1976 1.8627 1.5904 0.037 Uiso calc R 1 1
C C2 1.05129(18) 1.8131(2) 1.32364(19) 0.0179(3) Uani d . 1 1
C C3 0.93621(18) 1.60305(19) 1.20855(18) 0.0166(3) Uani d . 1 1
C C4 0.97991(18) 1.4674(2) 1.25479(18) 0.0174(3) Uani d . 1 1
H H4 1.0826 1.5113 1.3695 0.021 Uiso calc R 1 1
C C5 0.87715(18) 1.2701(2) 1.13753(19) 0.0174(3) Uani d . 1 1
H H5 0.9082 1.1802 1.1722 0.021 Uiso calc R 1 1
C C6 0.72738(18) 1.20521(19) 0.96773(18) 0.0166(3) Uani d . 1 1
C C7 0.67704(18) 1.3397(2) 0.92338(19) 0.0181(3) Uani d . 1 1
H H7 0.5714 1.2964 0.8115 0.022 Uiso calc R 1 1
C C8 0.78030(19) 1.5347(2) 1.04150(19) 0.0181(3) Uani d . 1 1
H H8 0.7455 1.6249 1.0095 0.022 Uiso calc R 1 1
C C9 0.67885(19) 0.86901(19) 0.86356(19) 0.0197(3) Uani d . 1 1
H H9A 0.6449 0.8585 0.9629 0.024 Uiso calc R 1 1
H H9B 0.8132 0.9049 0.9071 0.024 Uiso calc R 1 1
C C10 0.58484(18) 0.67807(19) 0.67576(19) 0.0172(3) Uani d . 1 1
C C11 0.64548(18) 0.64417(19) 0.52994(19) 0.0183(3) Uani d . 1 1
H H11 0.7453 0.7424 0.5498 0.022 Uiso calc R 1 1
C C12 0.56143(18) 0.4684(2) 0.35604(19) 0.0176(3) Uani d . 1 1
H H12 0.6038 0.4474 0.2576 0.021 Uiso calc R 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
C6 O2 C9 . . 117.64(10)
C2 C1 H1A . . 109.5
C2 C1 H1B . . 109.5
H1A C1 H1B . . 109.5
C2 C1 H1C . . 109.5
H1A C1 H1C . . 109.5
H1B C1 H1C . . 109.5
O1 C2 C3 . . 120.37(12)
O1 C2 C1 . . 120.78(12)
C3 C2 C1 . . 118.84(12)
C4 C3 C8 . . 117.90(13)
C4 C3 C2 . . 122.90(12)
C8 C3 C2 . . 119.15(12)
C5 C4 C3 . . 121.68(12)
C5 C4 H4 . . 119.2
C3 C4 H4 . . 119.2
C4 C5 C6 . . 119.14(13)
C4 C5 H5 . . 120.4
C6 C5 H5 . . 120.4
O2 C6 C7 . . 115.22(12)
O2 C6 C5 . . 124.87(12)
C7 C6 C5 . . 119.91(13)
C8 C7 C6 . . 120.06(12)
C8 C7 H7 . . 120.0
C6 C7 H7 . . 120.0
C7 C8 C3 . . 121.19(13)
C7 C8 H8 . . 119.4
C3 C8 H8 . . 119.4
O2 C9 C10 . . 108.13(10)
O2 C9 H9A . . 110.1
C10 C9 H9A . . 110.1
O2 C9 H9B . . 110.1
C10 C9 H9B . . 110.1
H9A C9 H9B . . 108.4
C11 C10 C12 . 2_666 118.81(13)
C11 C10 C9 . . 119.68(13)
C12 C10 C9 2_666 . 121.51(12)
C12 C11 C10 . . 120.58(13)
C12 C11 H11 . . 119.7
C10 C11 H11 . . 119.7
C11 C12 C10 . 2_666 120.60(12)
C11 C12 H12 . . 119.7
C10 C12 H12 2_666 . 119.7
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
O1 C2 . 1.2240(16)
O2 C6 . 1.3617(17)
O2 C9 . 1.4398(15)
C1 C2 . 1.5059(19)
C1 H1A . 0.9800
C1 H1B . 0.9800
C1 H1C . 0.9800
C2 C3 . 1.4866(19)
C3 C4 . 1.3964(19)
C3 C8 . 1.4035(19)
C4 C5 . 1.387(2)
C4 H4 . 0.9500
C5 C6 . 1.3972(19)
C5 H5 . 0.9500
C6 C7 . 1.3967(19)
C7 C8 . 1.375(2)
C7 H7 . 0.9500
C8 H8 . 0.9500
C9 C10 . 1.5020(18)
C9 H9A . 0.9900
C9 H9B . 0.9900
C10 C11 . 1.3931(19)
C10 C12 2_666 1.3954(19)
C11 C12 . 1.3864(19)
C11 H11 . 0.9500
C12 C10 2_666 1.3954(19)
C12 H12 . 0.9500
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
C11 H11 O1 2_787 0.95 2.54 3.4362(18) 157.6
C12 H12 Cg1 1_544 0.95 2.61 3.5078(17) 158
loop_
_iucr_refine_instructions_details
;
TITL 1 in P-1
CELL 0.71073   8.1286   8.1610   8.4878 116.164 106.328 100.196
ZERR    1.00   0.0012   0.0007   0.0006   0.005   0.007   0.007
LATT 1
SFAC C  H  O
UNIT 24  22  4
omit 2 -3 8
OMIT -2 51
HTAB C11 O1_$1
EQIV $1 2-x,3-y,2-z
L.S. 4
ACTA
BOND $H
SIZE 0.09 0.19 0.23
TEMP -173
WGHT    0.064400    0.098300
FVAR       0.33642
O1    3    1.006110    1.926518    1.277974    11.00000    0.02581    0.01676 =
         0.02412    0.01112    0.00768    0.00624
O2    3    0.622382    1.015026    0.835199    11.00000    0.02050    0.01152 =
         0.01823    0.00568    0.00239    0.00450
C1    1    1.226121    1.882485    1.493910    11.00000    0.02321    0.01625 =
         0.02362    0.00801    0.00297    0.00131
AFIX 137
H1A   2    1.290677    2.021377    1.549826    11.00000   -1.50000
H1B   2    1.303865    1.808558    1.452356    11.00000   -1.50000
H1C   2    1.197595    1.862659    1.590361    11.00000   -1.50000
AFIX   0
C2    1    1.051294    1.813123    1.323636    11.00000    0.01922    0.01614 =
         0.01769    0.00785    0.00891    0.00524
C3    1    0.936211    1.603047    1.208554    11.00000    0.01706    0.01615 =
         0.01641    0.00779    0.00798    0.00519
C4    1    0.979915    1.467384    1.254790    11.00000    0.01738    0.01855 =
         0.01368    0.00709    0.00499    0.00644
AFIX  43
H4    2    1.082646    1.511343    1.369475    11.00000   -1.20000
AFIX   0
C5    1    0.877153    1.270066    1.137534    11.00000    0.02064    0.01604 =
         0.01781    0.00993    0.00785    0.00793
AFIX  43
H5    2    0.908211    1.180210    1.172239    11.00000   -1.20000
AFIX   0
C6    1    0.727382    1.205209    0.967731    11.00000    0.01780    0.01432 =
         0.01580    0.00637    0.00757    0.00412
C7    1    0.677044    1.339709    0.923384    11.00000    0.01807    0.01793 =
         0.01508    0.00783    0.00411    0.00558
AFIX  43
H7    2    0.571358    1.296371    0.811494    11.00000   -1.20000
AFIX   0
C8    1    0.780297    1.534742    1.041501    11.00000    0.02074    0.01720 =
         0.01903    0.01108    0.00779    0.00797
AFIX  43
H8    2    0.745491    1.624925    1.009478    11.00000   -1.20000
AFIX   0
C9    1    0.678854    0.869010    0.863557    11.00000    0.02260    0.01540 =
         0.01899    0.00914    0.00462    0.00769
AFIX  23
H9A   2    0.644915    0.858486    0.962860    11.00000   -1.20000
H9B   2    0.813249    0.904903    0.907053    11.00000   -1.20000
AFIX   0
C10   1    0.584844    0.678074    0.675760    11.00000    0.01836    0.01432 =
         0.01896    0.00938    0.00503    0.00802
C11   1    0.645483    0.644169    0.529944    11.00000    0.01683    0.01652 =
         0.02249    0.01241    0.00596    0.00504
AFIX  43
H11   2    0.745308    0.742364    0.549844    11.00000   -1.20000
AFIX   0
C12   1    0.561434    0.468381    0.356037    11.00000    0.01935    0.01836 =
         0.01888    0.01147    0.00830    0.00890
AFIX  43
H12   2    0.603819    0.447442    0.257619    11.00000   -1.20000
HKLF 4
REM  1 in P-1
REM R1 =  0.0404 for   1472 Fo > 4sig(Fo)  and  0.0443 for all   1654 data
REM    128 parameters refined using      0 restraints
END
WGHT      0.0641      0.0986
REM Highest difference peak  0.204,  deepest hole -0.341,  1-sigma level  0.061
Q1    1   0.6473  0.6545  0.6380  11.00000  0.05    0.20
Q2    1   0.5478  0.6015  0.6770  11.00000  0.05    0.17
Q3    1   0.6878  0.8485  1.1814  11.00000  0.05    0.17
Q4    1   1.3478  1.9584  1.4860  11.00000  0.05    0.17
;
