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_7133360
_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_absolute_configuration rmad
_chemical_formula_moiety         'C20 H20 N2 O8, C10 H8'
_chemical_formula_sum            'C30 H28 N2 O8'
_chemical_formula_weight         544.54
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-07-27
_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                90
_cell_angle_beta                 96.9480(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.55420(10)
_cell_length_b                   7.02420(10)
_cell_length_c                   24.7028(3)
_cell_measurement_reflns_used    16994
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.8730
_cell_measurement_theta_min      3.6060
_cell_volume                     1301.16(3)
_computing_cell_refinement       'CrysAlisPro 1.171.42.70a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.70a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.70a (Rigaku OD, 2022)'
_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 1.000
_diffrn_measured_fraction_theta_max 0.983
_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    -92.00  35.00   0.50    2.00    --    0.00 -32.00-166.00  254
  2  \w    -30.00 140.00   0.50    2.00    --   57.86  32.00  -6.00  340
  3  \w   -177.00 -23.00   0.50    2.00    -- -106.00 -32.00-166.00  308
  4  \w     28.00 178.00   0.50    2.00    --  115.73  32.00  -6.00  300
  5  \w    -33.00  83.00   0.50    2.00    --    0.00  32.00  -6.00  232
  6  \w     -1.00  58.00   0.50    2.00    --    0.00 -99.00-180.00  118
  7  \w    -86.00 -13.00   0.50    2.00    --  -57.86 125.00   0.00  146
  8  \w    -14.00  25.00   0.50    2.00    --  -57.86  15.00-180.00   78
  9  \w    -30.00  25.00   0.50    2.00    --  -57.86  30.00 120.00  110
 10  \w   -143.00 -73.00   0.50    2.00    --  -57.86-125.00 -90.00  140
 11  \w    -34.00  35.00   0.50    2.00    --   57.86 -32.00-166.00  138
 12  \w      1.00  31.00   0.50    2.00    --   57.86  95.00  40.23   60
 13  \w      1.00  31.00   0.50    2.00    --   57.86  95.00 -98.66   60
 14  \w      0.00  27.00   0.50    2.00    --   57.86  98.00   0.64   54
 15  \w      0.00  27.00   0.50    2.00    --   57.86  98.00 173.04   54
 16  \w      1.00  28.00   0.50    2.00    --   57.86  97.00 106.20   54
 17  \w     10.00 140.00   0.50    2.00    --   57.86  77.00  60.00  260
 18  \w      1.00  28.00   0.50    2.00    --   57.86  97.00 -36.49   54
 19  \w    -29.00  51.00   0.50    2.00    --   57.86 -45.00  60.00  160
 20  \w   -177.00 -58.00   0.50    2.00    -- -106.00 -77.00 150.00  238
 21  \w   -177.00 -59.00   0.50    2.00    -- -106.00 -75.00  63.83  236
 22  \w   -177.00 -58.00   0.50    2.00    -- -106.00 -77.00 120.00  238
 23  \w   -177.00 -58.00   0.50    2.00    -- -106.00 -77.00  90.00  238
 24  \w   -177.00 -59.00   0.50    2.00    -- -106.00 -76.00  96.31  236
 25  \w   -177.00 -58.00   0.50    2.00    -- -106.00 -77.00 129.81  238
 26  \w   -177.00 -58.00   0.50    2.00    -- -106.00 -77.00  60.00  238
 27  \w   -177.00 -61.00   0.50    2.00    -- -106.00 -72.00  68.99  232
 28  \w   -177.00 -59.00   0.50    2.00    -- -106.00 -75.00  44.95  236
 29  \w    -55.00 -23.00   0.50    2.00    -- -106.00  50.00   0.00   64
 30  \w   -177.00 -62.00   0.50    2.00    -- -106.00 -68.00 129.19  230
 31  \w   -177.00 -58.00   0.50    2.00    -- -106.00 -77.00 108.06  238
 32  \w   -177.00 -34.00   0.50    2.00    -- -106.00 -37.00  90.00  286
 33  \w    -55.00 -23.00   0.50    2.00    -- -106.00  50.00-180.00   64
 34  \w     27.00 108.00   0.50    2.00    --  115.73-111.00  60.00  162
 35  \w     42.00 178.00   0.50    2.00    --  115.73  37.00  60.00  272
 36  \w     74.00 178.00   0.50    2.00    --  115.73  63.00  60.00  208
 37  \w     19.00 164.00   0.50    2.00    --  115.73   0.00-180.00  290
 38  \w     44.00  85.00   0.50    2.00    --  115.73  37.00  60.00   82
 39  \w    129.00 168.00   0.50    2.00    --  115.73  77.00  30.00   78
 40  \w     76.00 106.00   0.50    2.00    --  115.73  77.00  30.00   60
 41  \w     31.00  56.00   0.50    2.00    --  115.73 -50.00   0.00   50
 42  \w     82.00 108.00   0.50    2.00    --  115.73-111.00-180.00   52
 43  \w    112.00 157.00   0.50    2.00    --  115.73 111.00-120.00   90
 44  \w     39.00  78.00   0.50    2.00    --  115.73 -63.00  60.00   78
 45  \w     40.00  66.00   0.50    2.00    --  115.73-111.00-180.00   52
 46  \w     30.00  78.00   0.50    2.00    --  115.73 -63.00 -60.00   96
 47  \w     31.00  57.00   0.50    2.00    --  115.73 -50.00  30.00   52
 48  \w     78.00 143.00   0.50    2.00    --  115.73  77.00  90.00  130
 49  \w    107.00 174.00   0.50    2.00    --  115.73   0.00 -90.00  134
 50  \w    140.00 178.00   0.50    2.00    --  115.73  77.00 120.00   76
 51  \w     82.00 125.00   0.50    2.00    --  115.73  77.00 120.00   86
;
_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      0.0974066000
_diffrn_orient_matrix_UB_12      -0.0053931000
_diffrn_orient_matrix_UB_13      0.0585352000
_diffrn_orient_matrix_UB_21      0.1661009000
_diffrn_orient_matrix_UB_22      0.0894564000
_diffrn_orient_matrix_UB_23      -0.0202927000
_diffrn_orient_matrix_UB_31      -0.0716694000
_diffrn_orient_matrix_UB_32      0.2000193000
_diffrn_orient_matrix_UB_33      0.0106621000
_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  0.0193
_diffrn_reflns_av_unetI/netI     0.0154
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            19042
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.906
_diffrn_reflns_theta_min         3.605
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              PhotonJet-S
_exptl_absorpt_coefficient_mu    0.844
_exptl_absorpt_correction_T_max  0.983
_exptl_absorpt_correction_T_min  0.849
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.70a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_description       plate
_exptl_crystal_F_000             572
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.179
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details
;
 Flack x determined using 2196 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     367
_refine_ls_number_reflns         5020
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0259
_refine_ls_R_factor_gt           0.0257
_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^)+(0.0466P)^2^+0.1896P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0698
_refine_ls_wR_factor_ref         0.0701
_reflns_Friedel_coverage         0.805
_reflns_Friedel_fraction_full    0.983
_reflns_Friedel_fraction_max     0.939
_reflns_number_gt                4953
_reflns_number_total             5020
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc02229g2.cif
_cod_data_source_block           omr003_2_autored
_cod_depositor_comments
'Adding full bibliography for 7133359--7133360.cif.'
_cod_database_code               7133360
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C30 H28 N2 O8'
_shelx_estimated_absorpt_t_max   0.983
_shelx_estimated_absorpt_t_min   0.849
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C11(H11), C13(H13), C16(H16), C18(H18)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C4(H4), C21(H21), C22(H22), C23(H23), C24(H24), C25(H25), C26(H26),
 C27(H27), C28(H28)
2.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C19(H19A,H19B,H19C), C20(H20A,H20B,
 H20C)
2.d Idealised tetrahedral OH refined as rotating group:
 O6(H6), O8(H8)
;
_shelx_res_checksum              9692
_shelx_hkl_checksum              69627
_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 1.358
_oxdiff_exptl_absorpt_empirical_full_min 0.690