Facile synthesis of a 2,5-dihydroxyterephthalic acid-based charge transfer cocrystal for photoelectric applications
Yin, Pei-Pei; Chen, Yu-E; Diao, Jia-Wei; Cheng, Yi-Yang; Yang, Xiao-Gang; Liu, Bao-Zhong; Ma, Lu-Fang; CrystEngComm 26 (2024) 2746–2750; doi:10.1039/D4CE00338A

data_7248570
_publ_section_title
;
 Facile synthesis of a 2,5-dihydroxyterephthalic acid-based charge
 transfer cocrystal for photoelectric applications
;
_journal_issue                   21
_journal_name_full               CrystEngComm
_journal_page_first              2746
_journal_page_last               2750
_journal_paper_doi               10.1039/D4CE00338A
_journal_volume                  26
_journal_year                    2024
_chemical_formula_moiety         'C8 H5 O6, C12 H9 N2'
_chemical_formula_sum            'C20 H14 N2 O6'
_chemical_formula_weight         378.33
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-12-07
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2024-03-16 deposited with the CCDC.	2024-05-01 downloaded from the CCDC.
;
_cell_angle_alpha                64.656(10)
_cell_angle_beta                 78.043(8)
_cell_angle_gamma                66.903(9)
_cell_formula_units_Z            2
_cell_length_a                   9.0499(8)
_cell_length_b                   9.5985(10)
_cell_length_c                   11.2088(11)
_cell_measurement_reflns_used    1822
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.1370
_cell_measurement_theta_min      3.8390
_cell_volume                     808.51(16)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0584
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.833
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w     -7.00  22.00   1.00    8.00    --  -13.49 -99.00  30.00   29
  2  \w     -1.00  69.00   1.00    8.00    --   14.89  57.00  30.00   70
  3  \w     35.00  70.00   1.00    8.00    --   14.89 178.00 150.00   35
  4  \w     50.00  80.00   1.00    8.00    --   14.89  57.00 -60.00   30
  5  \w     -2.00  81.00   1.00    8.00    --   14.89  57.00 -90.00   83
  6  \w    -46.00  42.00   1.00    8.00    --   14.89 -77.00 150.00   88
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0272763000
_diffrn_orient_matrix_UB_12      -0.0588842000
_diffrn_orient_matrix_UB_13      -0.0292146000
_diffrn_orient_matrix_UB_21      -0.0644479000
_diffrn_orient_matrix_UB_22      0.0473642000
_diffrn_orient_matrix_UB_23      -0.0433365000
_diffrn_orient_matrix_UB_31      0.0487731000
_diffrn_orient_matrix_UB_32      0.0432298000
_diffrn_orient_matrix_UB_33      -0.0467140000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0244
_diffrn_reflns_av_unetI/netI     0.0544
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.833
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5919
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.833
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.282
_diffrn_reflns_theta_min         3.244
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.117
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93505
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.554
_exptl_crystal_description       block
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.206
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         3337
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0869
_refine_ls_R_factor_gt           0.0594
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0509P)^2^+0.3188P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1331
_refine_ls_wR_factor_ref         0.1503
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2218
_reflns_number_total             3337
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ce00338a2.cif
_cod_data_source_block           ljy-122
_cod_depositor_comments          'Adding full bibliography for 7248570.cif.'
_cod_database_code               7248570
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C1H1O1
_shelx_estimated_absorpt_t_max   0.983
_shelx_estimated_absorpt_t_min   0.967
_reflns_odcompleteness_completeness 99.73
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.30
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2A), C5(H5A), N2(H2), C9(H9), C10(H10), C11(H11), C13(H13), C14(H14),
 C16(H16), C17(H17), C18(H18)
2.b Idealised tetrahedral OH refined as rotating group:
 O3(H3), O5(H5), O6(H6)
;
_shelx_res_checksum              49709
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.277
_oxdiff_exptl_absorpt_empirical_full_min 0.782