Amino acid-appended pyromellitic diimide liquid materials, their photoluminescence, and the thermal response that turns the photoluminescence off.
Omura, Takumi; Morisako, Shogo; Isoda, Kyosuke; Chemical communications (Cambridge, England) 60 (2024) 9352–9355; doi:10.1039/d4cc02229g

data_7133359
_publ_section_title
;
 Amino acid-appended pyromellitic diimide liquid materials, their
 photoluminescence, and the thermal response that turns the
 photoluminescence off.
;
_journal_issue                   70
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              9352
_journal_page_last               9355
_journal_paper_doi               10.1039/d4cc02229g
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C14 H8 N2 O8'
_chemical_formula_sum            'C14 H8 N2 O8'
_chemical_formula_weight         332.22
_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             2023-09-13
_audit_creation_method
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2024-05-08 deposited with the CCDC.	2024-07-15 downloaded from the CCDC.
;
_cell_angle_alpha                87.739(4)
_cell_angle_beta                 85.844(3)
_cell_angle_gamma                80.408(4)
_cell_formula_units_Z            1
_cell_length_a                   4.9931(2)
_cell_length_b                   5.0550(3)
_cell_length_c                   12.7089(6)
_cell_measurement_reflns_used    3543
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.4890
_cell_measurement_theta_min      3.4640
_cell_volume                     315.34(3)
_computing_cell_refinement       'CrysAlisPro 1.171.42.100a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.100a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.100a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Rigaku HyPix-6000 area detector'
_diffrn_detector_area_resol_mean 10.0
_diffrn_detector_type            'HPC area detector'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.966
_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    -95.00 -31.00   0.50    0.20    --    0.00 160.00 178.00  128
  2  \w    -66.00  -7.00   0.50    0.20    --    0.00 117.00  27.00  118
  3  \w   -141.00 -50.00   0.50    0.50    --  -57.86-160.00 148.00  182
  4  \w   -110.00 -30.00   0.50    0.50    --  -57.86 160.00 178.00  160
  5  \w   -145.00 -78.00   0.50    0.50    --  -57.86-117.00 -59.00  134
  6  \w     73.00 139.00   0.50    0.50    --   57.86 160.00 178.00  132
  7  \w     29.00 109.00   0.50    0.50    --   57.86-117.00 -59.00  160
  8  \w     52.00 135.00   0.50    0.50    --   57.86-160.00 148.00  166
  9  \w   -141.00 -50.00   0.50    0.50    -- -106.00-160.00 148.00  182
 10  \w    -83.00 -27.00   0.50    0.50    -- -106.00 117.00  27.00  112
 11  \w     29.00 109.00   0.50    0.50    --  115.73-117.00 -59.00  160
 12  \w    100.00 178.00   0.50    0.50    --  115.73 117.00  27.00  156
 13  \w     52.00 136.00   0.50    0.50    --  115.73-160.00 148.00  168
 14  \w     72.00 158.00   0.50    0.50    --  115.73 160.00 178.00  172
 15  \w    -86.00  42.00   0.50    0.20    --    0.00 -57.00 -90.00  256
 16  \w    -14.00  25.00   0.50    0.50    --  -57.86  15.00 -90.00   78
 17  \w    -30.00  25.00   0.50    0.50    --  -57.86  30.00  60.00  110
 18  \w    -14.00  25.00   0.50    0.50    --  -57.86  15.00 -60.00   78
 19  \w   -160.00  25.00   0.50    0.50    --  -57.86   0.00  60.00  370
 20  \w    -30.00  25.00   0.50    0.50    --  -57.86  30.00-120.00  110
 21  \w    -30.00  25.00   0.50    0.50    --  -57.86  30.00 150.00  110
 22  \w    -86.00 -13.00   0.50    0.50    --  -57.86 125.00 120.00  146
 23  \w    -29.00  51.00   0.50    0.50    --   57.86 -45.00 -60.00  160
 24  \w      1.00  31.00   0.50    0.50    --   57.86  95.00 164.78   60
 25  \w    -55.00 -23.00   0.50    0.50    -- -106.00  50.00   0.00   64
 26  \w   -177.00 -23.00   0.50    0.50    -- -106.00   0.00  90.00  308
 27  \w    -75.00 -23.00   0.50    0.50    -- -106.00  63.00-150.00  104
 28  \w   -177.00 -23.00   0.50    0.50    -- -106.00   0.00 -60.00  308
 29  \w   -125.00 -39.00   0.50    0.50    -- -106.00 178.00 -90.00  172
 30  \w    -75.00 -23.00   0.50    0.50    -- -106.00  63.00-120.00  104
 31  \w   -177.00 -23.00   0.50    0.50    -- -106.00   0.00  30.00  308
 32  \w    -82.00 -27.00   0.50    0.50    -- -106.00 111.00  60.00  110
 33  \w    -75.00 -23.00   0.50    0.50    -- -106.00  63.00  30.00  104
 34  \w   -177.00 -23.00   0.50    0.50    -- -106.00   0.00-120.00  308
 35  \w    -55.00 -23.00   0.50    0.50    -- -106.00  50.00 -30.00   64
 36  \w   -173.00 -78.00   0.50    0.50    -- -106.00-117.00 -59.00  190
 37  \w     27.00 108.00   0.50    0.50    --  115.73-111.00   0.00  162
 38  \w     31.00  58.00   0.50    0.50    --  115.73 -50.00   0.00   54
 39  \w     31.00  58.00   0.50    0.50    --  115.73 -50.00  60.00   54
 40  \w     19.00 106.00   0.50    0.50    --  115.73 -91.00 150.00  174
 41  \w     27.00 108.00   0.50    0.50    --  115.73-111.00 150.00  162
 42  \w     14.00 178.00   0.50    0.50    --  115.73   0.00-180.00  328
 43  \w    103.00 178.00   0.50    0.50    --  115.73 111.00  60.00  150
 44  \w     31.00  58.00   0.50    0.50    --  115.73 -50.00 120.00   54
 45  \w    103.00 178.00   0.50    0.50    --  115.73 111.00 150.00  150
 46  \w     29.00  78.00   0.50    0.50    --  115.73 -63.00-180.00   98
 47  \w    -38.00  83.00   0.50    0.20    --    0.00  37.00  90.00  242
 48  \w     -1.00  58.00   0.50    0.20    --    0.00 -99.00-150.00  118
 49  \w    -96.00  48.00   0.50    0.20    --    0.00 -77.00 150.00  288
 50  \w   -143.00 -73.00   0.50    0.50    --  -57.86-125.00   0.00  140
 51  \w   -145.00  -2.00   0.50    0.50    --  -57.86 -45.00 -60.00  286
 52  \w   -144.00 -17.00   0.50    0.50    --  -57.86 -61.00  90.00  254
 53  \w      1.00  29.00   0.50    0.50    --   57.86  96.00-110.79   56
 54  \w     10.00 140.00   0.50    0.50    --   57.86  77.00  30.00  260
 55  \w      1.00  28.00   0.50    0.50    --   57.86  97.00  -7.82   54
 56  \w      2.00 140.00   0.50    0.50    --   57.86  45.00 -30.00  276
 57  \w     10.00 140.00   0.50    0.50    --   57.86  77.00  90.00  260
 58  \w      0.00  27.00   0.50    0.50    --   57.86  98.00-120.28   54
 59  \w      1.00  29.00   0.50    0.50    --   57.86  96.00 115.32   56
 60  \w      0.00  27.00   0.50    0.50    --   57.86  98.00 -67.32   54
 61  \w     17.00 140.00   0.50    0.50    --   57.86  61.00-150.00  246
 62  \w    -40.00  17.00   0.50    0.50    --   57.86 -15.00  30.00  114
 63  \w     10.00 140.00   0.50    0.50    --   57.86  77.00 120.00  260
 64  \w      2.00 140.00   0.50    0.50    --   57.86  45.00-120.00  276
 65  \w     42.00 143.00   0.50    0.50    --  115.73  37.00 120.00  202
 66  \w     42.00 178.00   0.50    0.50    --  115.73  37.00-150.00  272
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB Synergy-S'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1073972000
_diffrn_orient_matrix_UB_12      -0.0487271000
_diffrn_orient_matrix_UB_13      -0.1155000000
_diffrn_orient_matrix_UB_21      0.2945036000
_diffrn_orient_matrix_UB_22      -0.0458715000
_diffrn_orient_matrix_UB_23      0.0339959000
_diffrn_orient_matrix_UB_31      -0.0093009000
_diffrn_orient_matrix_UB_32      -0.3018739000
_diffrn_orient_matrix_UB_33      0.0169446000
_diffrn_radiation_monochromator  'multi-layer mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0355
_diffrn_reflns_av_unetI/netI     0.0236
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5676
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.515
_diffrn_reflns_theta_min         3.488
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              PhotonJet-S
_exptl_absorpt_coefficient_mu    1.282
_exptl_absorpt_correction_T_max  0.975
_exptl_absorpt_correction_T_min  0.740
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.100a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.749
_exptl_crystal_description       plate
_exptl_crystal_F_000             170
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.351
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     110
_refine_ls_number_reflns         1206
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0497
_refine_ls_R_factor_gt           0.0457
_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^)+(0.0943P)^2^+0.1092P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1343
_refine_ls_wR_factor_ref         0.1383
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1077
_reflns_number_total             1206
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc02229g2.cif
_cod_data_source_block           omr010_1_autored
_cod_depositor_comments
'Adding full bibliography for 7133359--7133360.cif.'
_cod_database_code               7133359
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C14 H8 N2 O8'
_shelx_estimated_absorpt_t_max   0.975
_shelx_estimated_absorpt_t_min   0.740
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1)
2.c Idealised tetrahedral OH refined as rotating group:
 O4(H4)
;
_shelx_res_checksum              31996
_shelx_hkl_checksum              58278
_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 1.494
_oxdiff_exptl_absorpt_empirical_full_min 0.603