#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/09/2200982.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_2200982
loop_
_publ_author_name
'Hökelek, Tuncer'
'Saripinar, Emïn'
'Yıldırım, Ismaïl'
'Akkurt, Mehmet'
'Akçamur, Yunus'
_publ_section_title
;
 4-(4-Methoxybenzoyl)-5-(4-methoxyphenyl)-2,3-dihydro-2,3-furandione
;
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o30
_journal_page_last               o32
_journal_paper_doi               10.1107/S1600536801020669
_journal_volume                  58
_journal_year                    2002
_chemical_formula_iupac          'C19 H14 O6'
_chemical_formula_moiety         'C19 H14 O6'
_chemical_formula_sum            'C19 H14 O6'
_chemical_formula_weight         338.3
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90
_cell_angle_beta                 96.197(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.3574(10)
_cell_length_b                   9.5422(10)
_cell_length_c                   19.775(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      18
_cell_measurement_theta_min      10
_cell_volume                     1567.8(3)
_computing_cell_refinement       'CAD-4 EXPRESS'
_computing_data_collection       'CAD-4 EXPRESS (Enraf-Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_diffrn_measurement_device_type  'Enraf-Nonius Turbo-CAD-4'
_diffrn_measurement_method       'non-profiled ω/2θ'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     .71073
_diffrn_reflns_av_R_equivalents  .019
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            2479
_diffrn_reflns_theta_full        24.2
_diffrn_reflns_theta_max         24.2
_diffrn_reflns_theta_min         2.37
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    .108
_exptl_absorpt_correction_T_max  .979
_exptl_absorpt_correction_T_min  .968
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(MolEN; Fair, 1990)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.433
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod-shaped
_exptl_crystal_F_000             704
_exptl_crystal_size_max          .3
_exptl_crystal_size_mid          .25
_exptl_crystal_size_min          .2
_refine_diff_density_max         .153
_refine_diff_density_min         -.215
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   .979
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         2300
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      .979
_refine_ls_R_factor_gt           .0448
_refine_ls_shift/su_max          .001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0507P)²]  where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .1158
_reflns_number_gt                1188
_reflns_number_total             2395
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            wn6074.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2200982
_cod_database_fobs_code          2200982
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_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
_atom_site_type_symbol
O6 .5005(3) .2114(2) 1.00187(13) .0570(7) Uani d . 1 . . O
C19 .5758(5) .1314(4) 1.0580(2) .0733(13) Uani d . 1 . . C
H19A .6388 .0576 1.0412 .11 Uiso calc R 1 . . H
H19B .4946 .0916 1.083 .11 Uiso calc R 1 . . H
H19C .6444 .1914 1.0874 .11 Uiso calc R 1 . . H
O1 .0380(3) .7298(2) .98265(11) .0437(6) Uani d . 1 . . O
O2 -.1373(3) .9064(2) .95772(12) .0523(7) Uani d . 1 . . O
O5 .7175(3) .8604(3) 1.30417(11) .0635(8) Uani d . 1 . . O
C16 .4062(4) .3205(4) 1.01637(18) .0427(9) Uani d . 1 . . C
O3 -.1266(3) .9238(3) 1.10754(12) .0622(7) Uani d . 1 . . O
C4 .1114(4) .6713(3) 1.04403(17) .0393(9) Uani d . 1 . . C
C13 .2095(4) .5512(3) 1.03394(17) .0377(8) Uani d . 1 . . C
C1 -.0614(4) .8368(4) .99964(18) .0417(9) Uani d . 1 . . C
C6 .2749(4) .7437(3) 1.20470(16) .0404(9) Uani d . 1 . . C
C3 .0671(4) .7371(3) 1.09969(17) .0389(9) Uani d . 1 . . C
C18 .2406(4) .5086(3) .96916(17) .0415(9) Uani d . 1 . . C
H18 .1958 .5584 .9313 .05 Uiso calc R 1 . . H
C15 .3731(4) .3577(4) 1.08106(18) .0466(9) Uani d . 1 . . C
H15 .4156 .306 1.1186 .056 Uiso calc R 1 . . H
C17 .3358(4) .3950(4) .96036(18) .0449(9) Uani d . 1 . . C
H17 .3535 .3673 .9167 .054 Uiso calc R 1 . . H
C14 .2769(4) .4716(3) 1.08922(17) .0443(9) Uani d . 1 . . C
H14 .2559 .4967 1.1328 .053 Uiso calc R 1 . . H
C10 .5311(4) .8602(4) 1.20126(16) .0522(10) Uani d . 1 . . C
H10 .6004 .9118 1.1772 .063 Uiso calc R 1 . . H
C11 .3825(4) .8196(4) 1.17067(16) .0481(10) Uani d . 1 . . C
H11 .3533 .844 1.1255 .058 Uiso calc R 1 . . H
O4 .0099(3) .6634(3) 1.20688(13) .0735(9) Uani d . 1 . . O
C5 .1131(5) .7083(3) 1.17384(17) .0466(10) Uani d . 1 . . C
C2 -.0492(4) .8425(4) 1.07723(18) .0456(9) Uani d . 1 . . C
C9 .5758(4) .8234(4) 1.26806(17) .0487(10) Uani d . 1 . . C
C8 .4738(5) .7415(4) 1.30239(17) .0576(11) Uani d . 1 . . C
H8 .5059 .7127 1.3467 .069 Uiso calc R 1 . . H
C7 .3262(5) .7030(4) 1.27137(17) .0555(10) Uani d . 1 . . C
H7 .2587 .6486 1.2951 .067 Uiso calc R 1 . . H
C12 .8156(5) .9598(4) 1.27410(19) .0679(12) Uani d . 1 . . C
H12A .9117 .9767 1.3042 .102 Uiso calc R 1 . . H
H12B .7573 1.046 1.2662 .102 Uiso calc R 1 . . H
H12C .844 .9237 1.2317 .102 Uiso calc R 1 . . H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0106 .006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
-2 3 4
-2 -1 8
4 0 4
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
O6 C19 H19A 109.5 ?
O6 C19 H19B 109.5 ?
H19A C19 H19B 109.5 ?
O6 C19 H19C 109.5 ?
H19A C19 H19C 109.5 ?
H19B C19 H19C 109.5 ?
C1 O1 C4 107.4(3) yes
C9 O5 C12 117.4(3) yes
C16 O6 C19 117.5(3) yes
O2 C1 C2 130.7(3) yes
O1 C1 C2 107.1(3) yes
O3 C2 C3 132.6(3) yes
C3 C2 C1 104.8(3) yes
C4 C3 C2 108.0(3) yes
C4 C3 C5 130.3(3) yes
C3 C4 O1 112.6(3) yes
C3 C4 C13 133.9(3) yes
O1 C4 C13 113.4(3) yes
O4 C5 C6 122.4(3) yes
O4 C5 C3 117.9(3) yes
C6 C5 C3 119.6(3) yes
C7 C6 C5 120.4(3) yes
O5 C9 C10 124.5(3) yes
O6 C16 C15 124.8(3) yes
O6 C16 C17 115.4(3) yes
C15 C16 C17 119.7(3) yes
C18 C13 C14 117.4(3) ?
C18 C13 C4 121.7(3) ?
C14 C13 C4 120.9(3) ?
O2 C1 O1 122.2(3) ?
C11 C6 C7 117.0(3) ?
C11 C6 C5 122.6(3) ?
C2 C3 C5 121.6(3) ?
C17 C18 C13 121.1(3) ?
C17 C18 H18 119.4 ?
C13 C18 H18 119.4 ?
C14 C15 C16 119.3(3) ?
C14 C15 H15 120.3 ?
C16 C15 H15 120.3 ?
C18 C17 C16 120.4(3) ?
C18 C17 H17 119.8 ?
C16 C17 H17 119.8 ?
C15 C14 C13 122.0(3) ?
C15 C14 H14 119 ?
C13 C14 H14 119 ?
C11 C10 C9 119.2(3) ?
C11 C10 H10 120.4 ?
C9 C10 H10 120.4 ?
C10 C11 C6 122.4(3) ?
C10 C11 H11 118.8 ?
C6 C11 H11 118.8 ?
O3 C2 C1 122.6(3) ?
O5 C9 C8 115.8(3) ?
C10 C9 C8 119.7(4) ?
C7 C8 C9 120.3(3) ?
C7 C8 H8 119.9 ?
C9 C8 H8 119.9 ?
C8 C7 C6 121.3(3) ?
C8 C7 H7 119.4 ?
C6 C7 H7 119.4 ?
O5 C12 H12A 109.5 ?
O5 C12 H12B 109.5 ?
H12A C12 H12B 109.5 ?
O5 C12 H12C 109.5 ?
H12A C12 H12C 109.5 ?
H12B C12 H12C 109.5 ?
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
C19 H19A . .96 ?
C19 H19B . .96 ?
C19 H19C . .96 ?
O1 C1 . 1.381(4) yes
O1 C4 . 1.414(4) yes
O2 C1 . 1.191(4) yes
O4 C5 . 1.215(4) yes
O5 C9 . 1.362(4) yes
O5 C12 . 1.425(4) yes
O6 C16 . 1.355(4) yes
O6 C19 . 1.436(4) yes
C16 C15 . 1.384(4) ?
C16 C17 . 1.392(4) ?
O3 C2 . 1.210(4) ?
C1 C2 . 1.528(5) yes
C3 C2 . 1.436(5) yes
C3 C5 . 1.501(5) yes
C4 C3 . 1.353(4) yes
C4 C13 . 1.435(4) yes
C13 C18 . 1.395(4) ?
C13 C14 . 1.399(4) ?
C6 C11 . 1.384(4) ?
C6 C7 . 1.397(4) ?
C6 C5 . 1.462(5) yes
C18 C17 . 1.367(4) ?
C18 H18 . .93 ?
C15 C14 . 1.372(4) ?
C15 H15 . .93 ?
C17 H17 . .93 ?
C14 H14 . .93 ?
C10 C11 . 1.377(4) ?
C10 C9 . 1.379(4) ?
C10 H10 . .93 ?
C11 H11 . .93 ?
C9 C8 . 1.387(5) ?
C8 C7 . 1.368(5) ?
C8 H8 . .93 ?
C7 H7 . .93 ?
C12 H12A . .96 ?
C12 H12B . .96 ?
C12 H12C . .96 ?
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
_geom_torsion_publ_flag
C1 O1 C4 C3 -1.3(3) ?
C1 O1 C4 C13 175.6(2) ?
C3 C4 C13 C18 -177.5(3) ?
O1 C4 C13 C18 6.5(4) ?
C3 C4 C13 C14 3.0(6) ?
O1 C4 C13 C14 -173.1(3) ?
C4 O1 C1 O2 178.9(3) ?
C4 O1 C1 C2 -.8(3) ?
C2 C3 C5 O4 64.2(4) yes
O1 C4 C3 C2 3.0(4) ?
C13 C4 C3 C2 -173.1(3) ?
O1 C4 C3 C5 178.8(3) ?
C13 C4 C3 C5 2.7(6) ?
C14 C13 C18 C17 -1.2(5) ?
C4 C13 C18 C17 179.2(3) ?
O6 C16 C15 C14 179.3(3) ?
C17 C16 C15 C14 -2.9(5) ?
C13 C18 C17 C16 -1.1(5) ?
O6 C16 C17 C18 -178.9(3) ?
C15 C16 C17 C18 3.2(5) ?
C16 C15 C14 C13 .6(5) ?
C18 C13 C14 C15 1.5(5) ?
C4 C13 C14 C15 -179.0(3) ?
C9 C10 C11 C6 .5(5) ?
C7 C6 C11 C10 -3.1(5) ?
C5 C6 C11 C10 175.9(3) ?
C11 C6 C5 O4 -167.1(3) yes
C7 C6 C5 O4 11.9(5) ?
C11 C6 C5 C3 8.6(5) yes
C7 C6 C5 C3 -172.5(3) ?
C4 C3 C5 O4 -111.2(4) ?
C4 C3 C5 C6 73.0(5) ?
C2 C3 C5 C6 -111.7(4) ?
C4 C3 C2 O3 177.2(4) ?
C5 C3 C2 O3 .9(6) ?
C4 C3 C2 C1 -3.3(3) ?
C5 C3 C2 C1 -179.5(3) ?
O2 C1 C2 O3 2.4(6) ?
O1 C1 C2 O3 -177.9(3) ?
O2 C1 C2 C3 -177.2(4) ?
O1 C1 C2 C3 2.5(3) ?
C12 O5 C9 C10 9.3(5) yes
C12 O5 C9 C8 -171.6(3) yes
C11 C10 C9 O5 -178.3(3) ?
C11 C10 C9 C8 2.7(5) ?
O5 C9 C8 C7 177.7(3) ?
C10 C9 C8 C7 -3.2(5) ?
C9 C8 C7 C6 .5(6) ?
C11 C6 C7 C8 2.6(5) ?
C5 C6 C7 C8 -176.4(3) ?
C19 O6 C16 C15 -2.2(5) yes
C19 O6 C16 C17 180.0(3) yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 10595802
