#------------------------------------------------------------------------------
#$Date: 2025-08-19 15:18:28 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301805 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/35/2223561.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_2223561
loop_
_publ_author_name
'Li, Wenkuan'
'Yin, Handong'
'Wen, Liyuan'
'Li, Kang'
'Fan, Weidong'
_publ_section_title
;
 3,3'-Oxybi[isobenzofuran-1(3H)-one]
;
_journal_coeditor_code           SJ2658
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2577
_journal_paper_doi               10.1107/S1600536809038914
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C16 H10 O5'
_chemical_formula_moiety         'C16 H10 O5'
_chemical_formula_sum            'C16 H10 O5'
_chemical_formula_weight         282.24
_chemical_name_systematic
;
3,3'-Oxybi[isobenzofuran-1(3H)-one]
;
_space_group_IT_number           7
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P -2yac'
_symmetry_space_group_name_H-M   'P 1 n 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                 91.3340(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   4.4449(6)
_cell_length_b                   6.4937(8)
_cell_length_c                   22.222(2)
_cell_measurement_reflns_used    1280
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      22.95
_cell_measurement_theta_min      2.749
_cell_volume                     641.24(13)
_computing_cell_refinement       'SAINT (Siemens, 1996)'
_computing_data_collection       'SMART (Siemens, 1996)'
_computing_data_reduction        'SAINT (Siemens, 1996)'
_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      298(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Siemens SMART CCD area-detector'
_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  0.0246
_diffrn_reflns_av_sigmaI/netI    0.0266
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            3081
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         1.83
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_T_max  0.9880
_exptl_absorpt_correction_T_min  0.9532
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.462
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             292
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.132
_refine_diff_density_min         -0.131
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         1139
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.007
_refine_ls_R_factor_all          0.0408
_refine_ls_R_factor_gt           0.0311
_refine_ls_shift/su_max_lt       0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0502P)²+0.0032P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0719
_refine_ls_wR_factor_ref         0.0780
_reflns_number_gt                972
_reflns_number_total             1139
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sj2658.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        641.25(13)
_cod_original_sg_symbol_Hall     '-P 2yac'
_cod_original_sg_symbol_H-M      'P n'
_cod_database_code               2223561
_cod_database_fobs_code          2223561
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y, 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
O O1 0.4119(4) 0.1516(3) 0.04946(8) 0.0445(5) Uani d . 1 . .
O O2 0.7298(5) 0.4086(3) 0.01338(9) 0.0511(6) Uani d . 1 . .
O O3 0.7306(7) 0.7164(3) -0.03192(13) 0.0742(8) Uani d . 1 . .
O O4 0.6010(5) 0.2116(3) 0.14674(10) 0.0581(6) Uani d . 1 . .
O O5 0.4721(8) 0.2569(4) 0.24282(12) 0.0859(9) Uani d . 1 . .
C C1 0.6000(7) 0.2076(5) 0.00288(13) 0.0401(7) Uani d . 1 . .
H H1 0.7583 0.1044 -0.0022 0.048 Uiso calc R 1 . .
C C2 0.6456(7) 0.5423(5) -0.03175(14) 0.0494(8) Uani d . 1 . .
C C3 0.4189(7) 0.2325(4) -0.05400(13) 0.0414(7) Uani d . 1 . .
C C4 0.4482(7) 0.4308(5) -0.07433(13) 0.0445(7) Uani d . 1 . .
C C5 0.3011(8) 0.4956(6) -0.12687(14) 0.0555(9) Uani d . 1 . .
H H5 0.3231 0.6295 -0.1409 0.067 Uiso calc R 1 . .
C C6 0.1225(9) 0.3563(6) -0.15739(15) 0.0620(10) Uani d . 1 . .
H H6 0.0207 0.3965 -0.1925 0.074 Uiso calc R 1 . .
C C7 0.0922(9) 0.1584(6) -0.13675(16) 0.0598(9) Uani d . 1 . .
H H7 -0.0305 0.0669 -0.1582 0.072 Uiso calc R 1 . .
C C8 0.2407(7) 0.0915(5) -0.08456(14) 0.0499(8) Uani d . 1 . .
H H8 0.2207 -0.0430 -0.0708 0.060 Uiso calc R 1 . .
C C9 0.5534(7) 0.0616(5) 0.10002(14) 0.0443(7) Uani d . 1 . .
H H9 0.7448 -0.0014 0.0890 0.053 Uiso calc R 1 . .
C C10 0.4522(8) 0.1563(5) 0.19777(15) 0.0561(9) Uani d . 1 . .
C C11 0.3520(6) -0.0951(4) 0.12751(13) 0.0383(7) Uani d . 1 . .
C C12 0.2908(6) -0.0361(5) 0.18517(12) 0.0398(7) Uani d . 1 . .
C C13 0.1088(8) -0.1539(6) 0.22104(14) 0.0527(8) Uani d . 1 . .
H H13 0.0671 -0.1132 0.2601 0.063 Uiso calc R 1 . .
C C14 -0.0088(8) -0.3326(5) 0.19756(16) 0.0567(9) Uani d . 1 . .
H H14 -0.1309 -0.4152 0.2209 0.068 Uiso calc R 1 . .
C C15 0.0531(8) -0.3905(5) 0.13930(15) 0.0565(9) Uani d . 1 . .
H H15 -0.0294 -0.5119 0.1240 0.068 Uiso calc R 1 . .
C C16 0.2336(7) -0.2733(5) 0.10336(14) 0.0475(8) Uani d . 1 . .
H H16 0.2740 -0.3131 0.0642 0.057 Uiso calc R 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
_geom_angle_publ_flag
C1 O1 C9 . . 116.0(2) ?
C2 O2 C1 . . 110.6(2) ?
C10 O4 C9 . . 110.7(2) ?
O1 C1 O2 . . 111.1(2) ?
O1 C1 C3 . . 109.6(2) ?
O2 C1 C3 . . 104.2(2) ?
O1 C1 H1 . . 110.6 ?
O2 C1 H1 . . 110.6 ?
C3 C1 H1 . . 110.6 ?
O3 C2 O2 . . 121.4(3) ?
O3 C2 C4 . . 130.6(3) ?
O2 C2 C4 . . 108.0(2) ?
C4 C3 C8 . . 121.3(3) ?
C4 C3 C1 . . 109.1(3) ?
C8 C3 C1 . . 129.6(3) ?
C3 C4 C5 . . 120.9(3) ?
C3 C4 C2 . . 108.1(3) ?
C5 C4 C2 . . 130.9(3) ?
C6 C5 C4 . . 118.1(3) ?
C6 C5 H5 . . 121.0 ?
C4 C5 H5 . . 121.0 ?
C7 C6 C5 . . 120.8(3) ?
C7 C6 H6 . . 119.6 ?
C5 C6 H6 . . 119.6 ?
C6 C7 C8 . . 121.5(4) ?
C6 C7 H7 . . 119.2 ?
C8 C7 H7 . . 119.2 ?
C3 C8 C7 . . 117.3(3) ?
C3 C8 H8 . . 121.3 ?
C7 C8 H8 . . 121.3 ?
O1 C9 O4 . . 110.6(2) ?
O1 C9 C11 . . 110.4(2) ?
O4 C9 C11 . . 104.2(2) ?
O1 C9 H9 . . 110.5 ?
O4 C9 H9 . . 110.5 ?
C11 C9 H9 . . 110.5 ?
O5 C10 O4 . . 121.4(3) ?
O5 C10 C12 . . 130.7(3) ?
O4 C10 C12 . . 107.9(3) ?
C12 C11 C16 . . 121.1(3) ?
C12 C11 C9 . . 109.0(3) ?
C16 C11 C9 . . 129.8(3) ?
C11 C12 C13 . . 121.1(3) ?
C11 C12 C10 . . 108.1(3) ?
C13 C12 C10 . . 130.8(3) ?
C14 C13 C12 . . 118.2(3) ?
C14 C13 H13 . . 120.9 ?
C12 C13 H13 . . 120.9 ?
C13 C14 C15 . . 120.3(3) ?
C13 C14 H14 . . 119.9 ?
C15 C14 H14 . . 119.9 ?
C16 C15 C14 . . 121.7(3) ?
C16 C15 H15 . . 119.2 ?
C14 C15 H15 . . 119.2 ?
C11 C16 C15 . . 117.5(3) ?
C11 C16 H16 . . 121.2 ?
C15 C16 H16 . . 121.2 ?
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
O1 C1 . 1.394(3) ?
O1 C9 . 1.403(4) ?
O2 C2 . 1.372(4) ?
O2 C1 . 1.444(4) ?
O3 C2 . 1.192(4) ?
O4 C10 . 1.374(4) ?
O4 C9 . 1.436(4) ?
O5 C10 . 1.197(4) ?
C1 C3 . 1.491(4) ?
C1 H1 . 0.9800 ?
C2 C4 . 1.467(4) ?
C3 C4 . 1.372(4) ?
C3 C8 . 1.379(4) ?
C4 C5 . 1.390(4) ?
C5 C6 . 1.373(5) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.372(5) ?
C6 H6 . 0.9300 ?
C7 C8 . 1.391(5) ?
C7 H7 . 0.9300 ?
C8 H8 . 0.9300 ?
C9 C11 . 1.495(4) ?
C9 H9 . 0.9800 ?
C10 C12 . 1.465(5) ?
C11 C12 . 1.371(4) ?
C11 C16 . 1.375(4) ?
C12 C13 . 1.380(4) ?
C13 C14 . 1.371(5) ?
C13 H13 . 0.9300 ?
C14 C15 . 1.382(5) ?
C14 H14 . 0.9300 ?
C15 C16 . 1.375(4) ?
C15 H15 . 0.9300 ?
C16 H16 . 0.9300 ?
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
C6 H6 O5 2_464 0.93 2.68 3.407(4) 135.9
C1 H1 O3 1_545 0.98 2.61 3.337(4) 131.3
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 350639
2 PubChem 6997466
