#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/23/2232355.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_2232355
loop_
_publ_author_name
'Al-Mohammed, Nassir N. N.'
'Alias, Yatimah'
'Abdullah, Zanariah'
'Khaledi, Hamid'
_publ_section_title
;
 1,1'-{2,2'-[1,4-Phenylenebis(methylene)]bis(oxy)bis(2,1-phenylene)}diethanone
;
_journal_coeditor_code           IS2792
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3016
_journal_paper_doi               10.1107/S1600536811042528
_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_common
;
1,1'-{2,2'-[1,4-Phenylenebis(methylene)]bis(oxy)bis(2,1-phenylene)}diethanone
;
_chemical_name_systematic
;
1-(2-{4-[(2-Acetylphenoxy)methyl]benzyloxy}phenyl)ethanone
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                   6.84900(10)
_cell_length_b                   15.0815(2)
_cell_length_c                   17.8519(3)
_cell_measurement_reflns_used    4755
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.53
_cell_measurement_theta_min      2.70
_cell_volume                     1843.98(5)
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0290
_diffrn_reflns_av_sigmaI/netI    0.0162
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            15454
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         2.70
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.9856
_exptl_absorpt_correction_T_min  0.9688
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.300
_refine_diff_density_min         -0.207
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         2013
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0428
_refine_ls_R_factor_gt           0.0350
_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)+(0.0539P)²+0.5451P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0946
_refine_ls_wR_factor_ref         0.0999
_reflns_number_gt                1728
_reflns_number_total             2013
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            is2792.cif
_cod_data_source_block           I
_cod_database_code               2232355
_cod_database_fobs_code          2232355
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, 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 0.04377(13) 0.42646(5) 0.16533(5) 0.0229(2) Uani d . 1 1
O O2 0.04118(12) 0.15272(5) 0.15468(4) 0.0159(2) Uani d . 1 1
C C1 0.07382(18) 0.31010(8) 0.07811(6) 0.0203(3) Uani d . 1 1
H H1A -0.0462 0.2780 0.0654 0.031 Uiso calc R 1 1
H H1B 0.1854 0.2696 0.0751 0.031 Uiso calc R 1 1
H H1C 0.0925 0.3591 0.0428 0.031 Uiso calc R 1 1
C C2 0.05802(16) 0.34623(7) 0.15636(6) 0.0165(3) Uani d . 1 1
C C3 0.05993(16) 0.28692(7) 0.22360(6) 0.0146(2) Uani d . 1 1
C C4 0.06897(16) 0.32882(8) 0.29338(6) 0.0171(3) Uani d . 1 1
H H4 0.0753 0.3917 0.2950 0.020 Uiso calc R 1 1
C C5 0.06905(17) 0.28253(8) 0.35995(7) 0.0187(3) Uani d . 1 1
H H5 0.0761 0.3130 0.4065 0.022 Uiso calc R 1 1
C C6 0.05866(16) 0.19058(8) 0.35781(6) 0.0177(3) Uani d . 1 1
H H6 0.0586 0.1579 0.4033 0.021 Uiso calc R 1 1
C C7 0.04836(16) 0.14611(7) 0.29006(6) 0.0160(2) Uani d . 1 1
H H7 0.0401 0.0832 0.2893 0.019 Uiso calc R 1 1
C C8 0.05005(15) 0.19348(7) 0.22261(6) 0.0140(2) Uani d . 1 1
C C9 0.02559(17) 0.05749(7) 0.15472(6) 0.0162(2) Uani d . 1 1
H H9A -0.0921 0.0387 0.1828 0.019 Uiso calc R 1 1
H H9B 0.1417 0.0308 0.1789 0.019 Uiso calc R 1 1
C C10 0.01168(16) 0.02795(7) 0.07449(6) 0.0152(2) Uani d . 1 1
C C11 0.17455(17) 0.03233(7) 0.02807(6) 0.0177(3) Uani d . 1 1
H H11 0.2946 0.0543 0.0472 0.021 Uiso calc R 1 1
C C12 0.16313(17) 0.00478(7) -0.04609(6) 0.0172(3) Uani d . 1 1
H H12 0.2750 0.0083 -0.0774 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
C8 O2 C9 . . 116.96(8)
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 . . 119.09(10)
O1 C2 C1 . . 119.05(10)
C3 C2 C1 . . 121.86(9)
C4 C3 C8 . . 117.69(10)
C4 C3 C2 . . 116.40(10)
C8 C3 C2 . . 125.90(10)
C5 C4 C3 . . 122.64(10)
C5 C4 H4 . . 118.7
C3 C4 H4 . . 118.7
C4 C5 C6 . . 118.80(10)
C4 C5 H5 . . 120.6
C6 C5 H5 . . 120.6
C7 C6 C5 . . 120.68(10)
C7 C6 H6 . . 119.7
C5 C6 H6 . . 119.7
C6 C7 C8 . . 120.24(10)
C6 C7 H7 . . 119.9
C8 C7 H7 . . 119.9
O2 C8 C7 . . 122.38(9)
O2 C8 C3 . . 117.68(9)
C7 C8 C3 . . 119.95(9)
O2 C9 C10 . . 107.45(8)
O2 C9 H9A . . 110.2
C10 C9 H9A . . 110.2
O2 C9 H9B . . 110.2
C10 C9 H9B . . 110.2
H9A C9 H9B . . 108.5
C12 C10 C11 5 . 119.34(10)
C12 C10 C9 5 . 120.48(10)
C11 C10 C9 . . 120.18(10)
C12 C11 C10 . . 120.54(11)
C12 C11 H11 . . 119.7
C10 C11 H11 . . 119.7
C11 C12 C10 . 5 120.12(11)
C11 C12 H12 . . 119.9
C10 C12 H12 5 . 119.9
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
O1 C2 . 1.2246(13)
O2 C8 . 1.3609(13)
O2 C9 . 1.4401(12)
C1 C2 . 1.5033(15)
C1 H1A . 0.9800
C1 H1B . 0.9800
C1 H1C . 0.9800
C2 C3 . 1.4970(15)
C3 C4 . 1.3982(15)
C3 C8 . 1.4109(15)
C4 C5 . 1.3783(16)
C4 H4 . 0.9500
C5 C6 . 1.3892(16)
C5 H5 . 0.9500
C6 C7 . 1.3846(15)
C6 H6 . 0.9500
C7 C8 . 1.4002(15)
C7 H7 . 0.9500
C9 C10 . 1.5029(15)
C9 H9A . 0.9900
C9 H9B . 0.9900
C10 C12 5 1.3907(16)
C10 C11 . 1.3912(16)
C11 C12 . 1.3897(16)
C11 H11 . 0.9500
C12 C10 5 1.3908(16)
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
C7 H7 O1 3_545 0.95 2.56 3.4649(14) 158.3
loop_
_iucr_refine_instructions_details
;
TITL sad
CELL 0.71073   6.8490  15.0815  17.8519  90.000  90.000  90.000
ZERR    4.00   0.0001   0.0002   0.0003   0.000   0.000   0.000
LATT 1
SYMM 0.5-X, -Y, 0.5+Z
SYMM -X, 0.5+Y, 0.5-Z
SYMM 0.5+X, 0.5-Y, -Z
SFAC C  H  O
UNIT 96  88  16
L.S. 12
BOND $H
ACTA
OMIT -2 54
eqiv $1 -x,-1/2+y,1/2-z
htab C7 O1_$1
SIZE 0.35 0.21 0.16
TEMP -173
WGHT    0.053900    0.545100
FVAR       0.10011
O1    3    0.043773    0.426465    0.165335    11.00000    0.03053    0.01267 =
         0.02535    0.00096   -0.00117    0.00015
O2    3    0.041183    0.152717    0.154683    11.00000    0.02388    0.00989 =
         0.01380   -0.00145   -0.00014   -0.00111
C1    1    0.073818    0.310100    0.078108    11.00000    0.02778    0.01569 =
         0.01756    0.00304   -0.00120   -0.00188
AFIX 137
H1A   2   -0.046163    0.278040    0.065414    11.00000   -1.50000
H1B   2    0.185382    0.269569    0.075087    11.00000   -1.50000
H1C   2    0.092535    0.359138    0.042813    11.00000   -1.50000
AFIX   0
C2    1    0.058019    0.346227    0.156358    11.00000    0.01445    0.01414 =
         0.02100    0.00162   -0.00128   -0.00100
C3    1    0.059926    0.286916    0.223597    11.00000    0.01309    0.01356 =
         0.01705   -0.00047   -0.00008    0.00008
C4    1    0.068965    0.328819    0.293377    11.00000    0.01721    0.01331 =
         0.02065   -0.00316   -0.00020    0.00002
AFIX  43
H4    2    0.075305    0.391716    0.294966    11.00000   -1.20000
AFIX   0
C5    1    0.069047    0.282533    0.359953    11.00000    0.01855    0.02132 =
         0.01624   -0.00561   -0.00012   -0.00075
AFIX  43
H5    2    0.076082    0.312966    0.406467    11.00000   -1.20000
AFIX   0
C6    1    0.058658    0.190577    0.357805    11.00000    0.01737    0.02075 =
         0.01503    0.00192    0.00023   -0.00068
AFIX  43
H6    2    0.058618    0.157863    0.403282    11.00000   -1.20000
AFIX   0
C7    1    0.048359    0.146115    0.290062    11.00000    0.01655    0.01340 =
         0.01817   -0.00004   -0.00045   -0.00013
AFIX  43
H7    2    0.040118    0.083241    0.289346    11.00000   -1.20000
AFIX   0
C8    1    0.050046    0.193479    0.222608    11.00000    0.01266    0.01473 =
         0.01474   -0.00218   -0.00045    0.00026
C9    1    0.025587    0.057492    0.154718    11.00000    0.02292    0.00971 =
         0.01594   -0.00017   -0.00013    0.00001
AFIX  23
H9A   2   -0.092063    0.038727    0.182766    11.00000   -1.20000
H9B   2    0.141696    0.030830    0.178878    11.00000   -1.20000
AFIX   0
C10   1    0.011681    0.027949    0.074490    11.00000    0.02204    0.00820 =
         0.01528   -0.00046   -0.00099    0.00182
C11   1    0.174551    0.032331    0.028068    11.00000    0.01766    0.01498 =
         0.02039   -0.00194   -0.00204   -0.00190
AFIX  43
H11   2    0.294551    0.054340    0.047216    11.00000   -1.20000
AFIX   0
C12   1    0.163134    0.004776   -0.046089    11.00000    0.01909    0.01335 =
         0.01929   -0.00080    0.00279   -0.00006
AFIX  43
H12   2    0.274951    0.008298   -0.077437    11.00000   -1.20000
HKLF 4
REM  sad in Pbca
REM R1 =  0.0350 for   1728 Fo > 4sig(Fo)  and  0.0428 for all   2013 data
REM    128 parameters refined using      0 restraints
END
WGHT      0.0535      0.5506
REM Highest difference peak  0.300,  deepest hole -0.207,  1-sigma level  0.042
Q1    1   0.0206  0.0404  0.1123  11.00000  0.05    0.30
Q2    1   0.0634  0.3139  0.1905  11.00000  0.05    0.27
Q3    1   0.0319  0.2469  0.2201  11.00000  0.05    0.24
Q4    1   0.0871  0.2448  0.2211  11.00000  0.05    0.23
;
