Synthesis of 3,3'-dihydroxy-2,2'-diindan-1,1'-dione derivatives for tautomeric organic semiconductors exhibiting intramolecular double proton transfer.
Nakano, Kyohei; Leong, Iat Wai; Hashizume, Daisuke; Bulgarevich, Kirill; Takimiya, Kazuo; Nishiyama, Yusuke; Yamazaki, Toshio; Tajima, Keisuke; Chemical science 14 (2023) 12205–12218; doi:10.1039/d3sc04125e

data_1570124
_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         'C20 H14 O4'
_chemical_formula_sum            'C20 H14 O4'
_chemical_formula_weight         318.31
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual-space
_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                104.134(3)
_cell_angle_beta                 97.329(4)
_cell_angle_gamma                100.536(3)
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_cell_length_b                   9.6097(3)
_cell_length_c                   10.9769(4)
_cell_measurement_reflns_used    8330
_cell_measurement_temperature    90.00(10)
_cell_measurement_theta_max      29.5730
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_cell_volume                     366.59(3)
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.42.57a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_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_temperature      90.00(10)
_diffrn_detector_area_resol_mean 10
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.899
_diffrn_measurement_device_type  'Rigaku AFC-11 with HyPix6000HE'
_diffrn_measurement_method       \w-scan
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0345
_diffrn_reflns_av_unetI/netI     0.0133
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.899
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            24415
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.899
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.925
_diffrn_reflns_theta_min         1.945
_diffrn_source                   'Fine-focus rotating anode'
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.830
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
 CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
 Numerical absorption correction based on gaussian integration over
 a multifaceted crystal model
 Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'dark red'
_exptl_crystal_density_diffrn    1.442
_exptl_crystal_description       needle
_exptl_crystal_F_000             166
_exptl_crystal_size_max          0.470
_exptl_crystal_size_mid          0.027
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.383
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.114
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     135
_refine_ls_number_reflns         1919
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.114
_refine_ls_R_factor_all          0.0566
_refine_ls_R_factor_gt           0.0492
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0768P)^2^+0.1271P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1492
_refine_ls_wR_factor_ref         0.1533
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1637
_reflns_number_total             1919
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc04125e2.cif
_cod_data_source_block           2
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Gaussian' was
changed to 'gaussian' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 1570123--1570129.cif.
;
_cod_database_code               1570124
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.954
_shelx_estimated_absorpt_t_max   0.998
_shelx_res_checksum              14428