#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/27/2232798.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_2232798
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(3,1-phenylene)}diethanone
;
_journal_coeditor_code           IS2798
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3140
_journal_paper_doi               10.1107/S1600536811045041
_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(3,1-phenylene)}diethanone
;
_space_group_IT_number           12
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2y'
_symmetry_space_group_name_H-M   'C 1 2/m 1'
_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                 93.083(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   20.6446(9)
_cell_length_b                   7.0205(4)
_cell_length_c                   6.5523(3)
_cell_measurement_reflns_used    1083
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.48
_cell_measurement_theta_min      3.07
_cell_volume                     948.29(8)
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and 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  0.0235
_diffrn_reflns_av_sigmaI/netI    0.0261
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            3981
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         3.07
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.9956
_exptl_absorpt_correction_T_min  0.9765
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             396
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.205
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     83
_refine_ls_number_reflns         1120
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0513
_refine_ls_R_factor_gt           0.0395
_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)+(0.0450P)²+0.5308P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0994
_refine_ls_wR_factor_ref         0.1067
_reflns_number_gt                872
_reflns_number_total             1120
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            is2798.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/m'
_cod_database_code               2232798
_cod_database_fobs_code          2232798
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'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 0.09646(6) 0.0000 0.6315(2) 0.0420(4) Uani d S 1 2
O O2 0.35997(5) 0.0000 0.31330(17) 0.0303(4) Uani d S 1 2
C C1 0.11430(9) 0.0000 0.2772(3) 0.0379(5) Uani d S 1 2
H H1A 0.1278 -0.1190 0.2140 0.057 Uiso calc PR 0.50 1
H H1B 0.1340 0.1082 0.2090 0.057 Uiso calc PR 0.50 1
H H1C 0.0669 0.0109 0.2635 0.057 Uiso calc PR 0.50 1
C C2 0.13609(9) 0.0000 0.5003(3) 0.0305(4) Uani d S 1 2
C C3 0.20700(8) 0.0000 0.5583(3) 0.0266(4) Uani d S 1 2
C C4 0.22729(9) 0.0000 0.7659(3) 0.0366(5) Uani d S 1 2
H H4 0.1961 0.0000 0.8674 0.044 Uiso calc SR 1 2
C C5 0.29237(9) 0.0000 0.8226(3) 0.0383(5) Uani d S 1 2
H H5 0.3058 0.0000 0.9636 0.046 Uiso calc SR 1 2
C C6 0.33890(8) 0.0000 0.6764(3) 0.0294(4) Uani d S 1 2
H H6 0.3838 0.0000 0.7170 0.035 Uiso calc SR 1 2
C C7 0.31899(8) 0.0000 0.4707(2) 0.0255(4) Uani d S 1 2
C C8 0.25302(8) 0.0000 0.4124(3) 0.0258(4) Uani d S 1 2
H H8 0.2396 0.0000 0.2715 0.031 Uiso calc SR 1 2
C C9 0.42832(8) 0.0000 0.3689(3) 0.0276(4) Uani d S 1 2
H H9A 0.4399 -0.1144 0.4514 0.033 Uiso d R 1 1
C C10 0.46469(8) 0.0000 0.1763(3) 0.0258(4) Uani d S 1 2
C C11 0.48225(6) 0.1701(2) 0.08780(18) 0.0310(3) Uani d . 1 1
H H11 0.4701 0.2875 0.1468 0.037 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
C7 O2 C9 . . 116.56(12)
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 . . 120.47(17)
O1 C2 C1 . . 120.54(17)
C3 C2 C1 . . 118.99(16)
C8 C3 C4 . . 119.34(16)
C8 C3 C2 . . 121.66(16)
C4 C3 C2 . . 119.00(16)
C5 C4 C3 . . 119.93(17)
C5 C4 H4 . . 120.0
C3 C4 H4 . . 120.0
C4 C5 C6 . . 120.95(17)
C4 C5 H5 . . 119.5
C6 C5 H5 . . 119.5
C7 C6 C5 . . 119.27(16)
C7 C6 H6 . . 120.4
C5 C6 H6 . . 120.4
O2 C7 C6 . . 124.68(15)
O2 C7 C8 . . 115.34(14)
C6 C7 C8 . . 119.98(15)
C3 C8 C7 . . 120.52(15)
C3 C8 H8 . . 119.7
C7 C8 H8 . . 119.7
O2 C9 C10 . . 108.37(13)
O2 C9 H9A . . 110.0
C10 C9 H9A . . 110.0
C11 C10 C11 . 6 119.26(16)
C11 C10 C9 . . 120.36(8)
C11 C10 C9 6 . 120.36(8)
C10 C11 C11 . 2_655 120.37(8)
C10 C11 H11 . . 119.8
C11 C11 H11 2_655 . 119.8
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
O1 C2 . 1.218(2)
O2 C7 . 1.3685(19)
O2 C9 . 1.4382(19)
C1 C2 . 1.506(3)
C1 H1A . 0.9800
C1 H1B . 0.9800
C1 H1C . 0.9800
C2 C3 . 1.493(2)
C3 C8 . 1.383(2)
C3 C4 . 1.402(3)
C4 C5 . 1.375(3)
C4 H4 . 0.9500
C5 C6 . 1.393(2)
C5 H5 . 0.9500
C6 C7 . 1.388(2)
C6 H6 . 0.9500
C7 C8 . 1.394(2)
C8 H8 . 0.9500
C9 C10 . 1.503(2)
C9 H9A . 0.9900
C10 C11 . 1.3844(16)
C10 C11 6 1.3844(16)
C11 C11 2_655 1.397(2)
C11 H11 . 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
C5 H5 O2 1_556 0.95 2.50 3.435(2) 170
C11 H11 O1 4_556 0.95 2.54 3.4215(16) 155
C6 H6 Cg 1_556 0.95 2.95 3.8469(19) 157
loop_
_iucr_refine_instructions_details
;
TITL 1 in C2/m
CELL 0.71073  20.6446   7.0205   6.5523  90.000  93.083  90.000
ZERR    2.00   0.0009   0.0004   0.0003   0.000   0.003   0.000
LATT 7
SYMM -X, Y, -Z
SFAC C  H  O
UNIT 48  44  8
L.S. 24
OMIT -2 54
OMIT 2 0 0
HTAB C5 O2_$1
HTAB C11 O1_$2
EQIV $1 x,y,1+z
EQIV $2 1/2-x,1/2+y,1-z
ACTA
BOND $H
SIZE 0.05 0.15 0.27
TEMP -173
WGHT    0.045000    0.530800
FVAR       0.15411
O1    3    0.096458    0.000000    0.631527    10.50000    0.02414    0.05791 =
         0.04518    0.00000    0.01210    0.00000
O2    3    0.359967    0.000000    0.313301    10.50000    0.01505    0.05862 =
         0.01738    0.00000    0.00143    0.00000
C1    1    0.114302    0.000000    0.277202    10.50000    0.01993    0.05221 =
         0.04091    0.00000   -0.00375    0.00000
AFIX 137
H1A   2    0.127839   -0.119017    0.213964    10.50000   -1.50000
H1B   2    0.133953    0.108158    0.208992    10.50000   -1.50000
H1C   2    0.066942    0.010859    0.263483    10.50000   -1.50000
AFIX   0
C2    1    0.136086    0.000000    0.500330    10.50000    0.02196    0.03356 =
         0.03645    0.00000    0.00549    0.00000
C3    1    0.207002    0.000000    0.558314    10.50000    0.02096    0.03405 =
         0.02509    0.00000    0.00288    0.00000
C4    1    0.227291    0.000000    0.765946    10.50000    0.02800    0.05873 =
         0.02386    0.00000    0.00883    0.00000
AFIX  43
H4    2    0.196096    0.000000    0.867378    10.50000   -1.20000
AFIX   0
C5    1    0.292373    0.000000    0.822618    10.50000    0.03144    0.06564 =
         0.01784    0.00000    0.00285    0.00000
AFIX  43
H5    2    0.305813    0.000000    0.963580    10.50000   -1.20000
AFIX   0
C6    1    0.338903    0.000000    0.676351    10.50000    0.02105    0.04593 =
         0.02108    0.00000   -0.00084    0.00000
AFIX  43
H6    2    0.383777    0.000000    0.716958    10.50000   -1.20000
AFIX   0
C7    1    0.318991    0.000000    0.470678    10.50000    0.02201    0.03573 =
         0.01888    0.00000    0.00359    0.00000
C8    1    0.253024    0.000000    0.412446    10.50000    0.02185    0.03546 =
         0.01993    0.00000   -0.00044    0.00000
AFIX  43
H8    2    0.239578    0.000000    0.271490    10.50000   -1.20000
AFIX   0
C9    1    0.428319    0.000000    0.368858    10.50000    0.01541    0.04660 =
         0.02063    0.00000   -0.00010    0.00000
AFIX   3
H9A   2    0.439864   -0.114359    0.451413    11.00000   -1.20000
AFIX   0
C10   1    0.464694    0.000000    0.176254    10.50000    0.01449    0.04291 =
         0.01996    0.00000   -0.00030    0.00000
C11   1    0.482249    0.170133    0.087799    11.00000    0.02576    0.04015 =
         0.02739   -0.00368    0.00440    0.00156
AFIX  43
H11   2    0.470089    0.287537    0.146842    11.00000   -1.20000
HKLF 4
REM  sad in C2/m
REM R1 =  0.0395 for    872 Fo > 4sig(Fo)  and  0.0513 for all   1120 data
REM     83 parameters refined using      0 restraints
END
WGHT      0.0442      0.5153
REM Highest difference peak  0.260,  deepest hole -0.205,  1-sigma level  0.036
Q1    1   0.4492  0.0000  0.2706  10.50000  0.05    0.26
Q2    1   0.3288  0.0000  0.5759  10.50000  0.05    0.26
Q3    1   0.1758  0.0000  0.5267  10.50000  0.05    0.22
Q4    1   0.2189  0.0000  0.6531  10.50000  0.05    0.19
;
