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#$Date: 2024-01-06 09:18:14 +0200 (Sat, 06 Jan 2024) $
#$Revision: 288731 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/01/1570129.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1570129
loop_
_publ_author_name
'Nakano, Kyohei'
'Leong, Iat Wai'
'Hashizume, Daisuke'
'Bulgarevich, Kirill'
'Takimiya, Kazuo'
'Nishiyama, Yusuke'
'Yamazaki, Toshio'
'Tajima, Keisuke'
_publ_section_title
;
 Synthesis of 3,3'-dihydroxy-2,2'-diindan-1,1'-dione derivatives for
 tautomeric organic semiconductors exhibiting intramolecular double proton
 transfer.
;
_journal_issue                   43
_journal_name_full               'Chemical science'
_journal_page_first              12205
_journal_page_last               12218
_journal_paper_doi               10.1039/d3sc04125e
_journal_volume                  14
_journal_year                    2023
_chemical_formula_moiety         'C26 H14 O4'
_chemical_formula_sum            'C26 H14 O4'
_chemical_formula_weight         390.37
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2022-11-02 deposited with the CCDC.	2023-10-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.1836(8)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.99456(7)
_cell_length_b                   6.49263(4)
_cell_length_c                   15.52347(11)
_cell_measurement_reflns_used    66672
_cell_measurement_temperature    89.9(4)
_cell_measurement_theta_max      61.9360
_cell_measurement_theta_min      2.2940
_cell_volume                     878.909(11)
_computing_cell_refinement       'CrysAlisPro 1.171.42.4a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.42.4a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.42.4a (Rigaku OD, 2021)'
_computing_molecular_graphics    SHELXLE
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    SHELXT-2018/2
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      89.9(4)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC11 (RINC): quarter-chi single'
_diffrn_measurement_method       ω-scan
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_av_unetI/netI     0.0140
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            142224
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         62.221
_diffrn_reflns_theta_min         2.336
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66866
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.4a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'Metallic Blue'
_exptl_crystal_density_diffrn    1.475
_exptl_crystal_description       block
_exptl_crystal_F_000             404
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.070
_refine_diff_density_max         0.658
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         14123
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0325
_refine_ls_R_factor_gt           0.0294
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0620P)²+0.0189P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0933
_refine_ls_wR_factor_ref         0.0954
_reflns_Friedel_coverage         0.000
_reflns_number_gt                12979
_reflns_number_total             14123
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3sc04125e2.cif
_cod_data_source_block           11
_cod_depositor_comments
'Adding full bibliography for 1570123--1570129.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1570129
_shelx_shelxl_version_number     2018/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.966
_shelx_estimated_absorpt_t_max   0.993
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.30194(2) 0.66482(2) 0.58750(2) 0.01274(2) Uani 1 1 d . . . . .
H1 H 0.3484(8) 0.5273(12) 0.6144(5) 0.0384(19) Uiso 1 1 d . . . . .
O2 O 0.56985(2) 0.67156(2) 0.35836(2) 0.01237(2) Uani 1 1 d . . . . .
C1 C 0.46139(2) 0.59601(2) 0.48364(2) 0.00859(2) Uani 1 1 d . . . . .
C2 C 0.35551(2) 0.70525(2) 0.51828(2) 0.00915(2) Uani 1 1 d . . . . .
C3 C 0.30384(2) 0.89063(2) 0.46543(2) 0.00931(2) Uani 1 1 d . . . . .
C4 C 0.20120(2) 1.03912(3) 0.47384(2) 0.01050(2) Uani 1 1 d . . . . .
H4 H 0.1481(8) 1.0351(12) 0.5238(5) 0.0315(17) Uiso 1 1 d . . . . .
C5 C 0.17370(2) 1.20445(2) 0.41060(2) 0.01011(2) Uani 1 1 d . . . . .
C6 C 0.06597(2) 1.36024(3) 0.41457(2) 0.01264(2) Uani 1 1 d . . . . .
H6 H 0.0075(7) 1.3492(10) 0.4605(4) 0.0226(14) Uiso 1 1 d . . . . .
C7 C 0.04039(2) 1.52051(3) 0.35413(2) 0.01443(3) Uani 1 1 d . . . . .
H7 H -0.0422(7) 1.6339(11) 0.3540(5) 0.0345(17) Uiso 1 1 d . . . . .
C8 C 0.12248(2) 1.53145(3) 0.28772(2) 0.01421(3) Uani 1 1 d . . . . .
H8 H 0.1050(8) 1.6536(11) 0.2451(5) 0.0354(18) Uiso 1 1 d . . . . .
C9 C 0.22807(2) 1.38015(3) 0.28200(2) 0.01246(2) Uani 1 1 d . . . . .
H9 H 0.2881(8) 1.3824(11) 0.2353(5) 0.0329(17) Uiso 1 1 d . . . . .
C10 C 0.25519(2) 1.21316(2) 0.34240(2) 0.01010(2) Uani 1 1 d . . . . .
C11 C 0.36254(2) 1.05327(3) 0.33629(2) 0.01043(2) Uani 1 1 d . . . . .
H11 H 0.4225(7) 1.0594(12) 0.2887(5) 0.0310(17) Uiso 1 1 d . . . . .
C12 C 0.38300(2) 0.89722(2) 0.39667(2) 0.00933(2) Uani 1 1 d . . . . .
C13 C 0.48299(2) 0.71272(2) 0.40752(2) 0.00912(2) Uani 1 1 d . . . . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C13 106.697(13) . . ?
C2 C1 C1 127.765(17) . 3_666 ?
C13 C1 C1 125.534(16) . 3_666 ?
O1 C2 C1 129.637(15) . . ?
O1 C2 C3 119.631(14) . . ?
C1 C2 C3 110.731(13) . . ?
C4 C3 C12 121.755(14) . . ?
C4 C3 C2 131.005(14) . . ?
C12 C3 C2 107.240(13) . . ?
C3 C4 C5 118.095(15) . . ?
C6 C5 C10 119.072(15) . . ?
C6 C5 C4 120.735(16) . . ?
C10 C5 C4 120.193(14) . . ?
C7 C6 C5 120.758(18) . . ?
C6 C7 C8 120.305(17) . . ?
C9 C8 C7 120.125(17) . . ?
C8 C9 C10 120.720(18) . . ?
C9 C10 C5 119.004(15) . . ?
C9 C10 C11 121.295(16) . . ?
C5 C10 C11 119.701(14) . . ?
C12 C11 C10 118.149(15) . . ?
C11 C12 C3 122.086(14) . . ?
C11 C12 C13 130.937(14) . . ?
C3 C12 C13 106.974(13) . . ?
O2 C13 C1 127.805(15) . . ?
O2 C13 C12 123.847(14) . . ?
C1 C13 C12 108.346(12) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.30740(19) . ?
O2 C13 1.24750(19) . ?
C1 C2 1.3964(2) . ?
C1 C13 1.4563(2) . ?
C1 C1 1.4566(3) 3_666 ?
C2 C3 1.4666(2) . ?
C3 C4 1.3630(2) . ?
C3 C12 1.4214(2) . ?
C4 C5 1.4346(2) . ?
C5 C6 1.4125(2) . ?
C5 C10 1.4288(2) . ?
C6 C7 1.3821(3) . ?
C7 C8 1.4092(3) . ?
C8 C9 1.3842(3) . ?
C9 C10 1.4150(2) . ?
C10 C11 1.4366(2) . ?
C11 C12 1.3618(2) . ?
C12 C13 1.4825(2) . ?
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C13 C1 C2 O1 -178.432(17) . . . . ?
C1 C1 C2 O1 0.85(3) 3_666 . . . ?
C13 C1 C2 C3 1.147(18) . . . . ?
C1 C1 C2 C3 -179.57(2) 3_666 . . . ?
O1 C2 C3 C4 -1.33(3) . . . . ?
C1 C2 C3 C4 179.041(17) . . . . ?
O1 C2 C3 C12 178.612(16) . . . . ?
C1 C2 C3 C12 -1.015(18) . . . . ?
C12 C3 C4 C5 0.27(3) . . . . ?
C2 C3 C4 C5 -179.787(16) . . . . ?
C3 C4 C5 C6 178.486(16) . . . . ?
C3 C4 C5 C10 -1.37(3) . . . . ?
C10 C5 C6 C7 -0.70(3) . . . . ?
C4 C5 C6 C7 179.442(17) . . . . ?
C5 C6 C7 C8 -0.38(3) . . . . ?
C6 C7 C8 C9 0.77(3) . . . . ?
C7 C8 C9 C10 -0.04(3) . . . . ?
C8 C9 C10 C5 -1.03(3) . . . . ?
C8 C9 C10 C11 178.937(17) . . . . ?
C6 C5 C10 C9 1.39(2) . . . . ?
C4 C5 C10 C9 -178.747(16) . . . . ?
C6 C5 C10 C11 -178.579(16) . . . . ?
C4 C5 C10 C11 1.28(2) . . . . ?
C9 C10 C11 C12 179.968(16) . . . . ?
C5 C10 C11 C12 -0.06(2) . . . . ?
C10 C11 C12 C3 -1.06(3) . . . . ?
C10 C11 C12 C13 179.687(16) . . . . ?
C4 C3 C12 C11 0.98(3) . . . . ?
C2 C3 C12 C11 -178.970(16) . . . . ?
C4 C3 C12 C13 -179.609(15) . . . . ?
C2 C3 C12 C13 0.440(17) . . . . ?
C2 C1 C13 O2 178.714(17) . . . . ?
C1 C1 C13 O2 -0.59(3) 3_666 . . . ?
C2 C1 C13 C12 -0.852(18) . . . . ?
C1 C1 C13 C12 179.843(19) 3_666 . . . ?
C11 C12 C13 O2 -0.01(3) . . . . ?
C3 C12 C13 O2 -179.347(16) . . . . ?
C11 C12 C13 C1 179.578(17) . . . . ?
C3 C12 C13 C1 0.240(18) . . . . ?
