Multi-color luminescent crystals derived from dynamic diastereomers of a perylene-substituted binaphthol derivative.
Yano, Riko; Ito, Suguru; Chemical communications (Cambridge, England) 61 (2025) 5305–5308; doi:10.1039/d5cc00758e

data_7134302
_publ_section_title
;
 Multi-color luminescent crystals derived from dynamic diastereomers of a
 perylene-substituted binaphthol derivative.
;
_journal_issue                   28
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              5305
_journal_page_last               5308
_journal_paper_doi               10.1039/d5cc00758e
_journal_volume                  61
_journal_year                    2025
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C42 H28 O2'
_chemical_formula_sum            'C42 H28 O2'
_chemical_formula_weight         564.64
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_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             2025-03-05
_audit_creation_method
;
Olex2 1.5
(compiled 2024.01.12 svn.r2f8d729c for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2025-03-06 deposited with the CCDC.	2025-03-06 downloaded from the CCDC.
;
_cell_angle_alpha                76.600(3)
_cell_angle_beta                 89.561(2)
_cell_angle_gamma                72.009(3)
_cell_formula_units_Z            2
_cell_length_a                   7.8625(2)
_cell_length_b                   10.7582(4)
_cell_length_c                   18.3210(5)
_cell_measurement_reflns_used    8249
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      74.76
_cell_measurement_theta_min      4.96
_cell_volume                     1430.38(8)
_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      123.15
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0605
_diffrn_reflns_av_unetI/netI     0.0687
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            32394
_diffrn_reflns_point_group_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.935
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.142
_diffrn_reflns_theta_min         4.975
_exptl_absorpt_coefficient_mu    0.616
_exptl_absorpt_correction_T_max  0.940
_exptl_absorpt_correction_T_min  0.631
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.66a (Rigaku Oxford Diffraction, 2019)

Empirical absorption correction using spherical harmonics,

 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_description       needle
_exptl_crystal_F_000             592
_exptl_crystal_preparation       Luminescent,Luminescent,Luminescent
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: MeOH/EtOAc'
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.204
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details
;
 Flack x determined using 3198 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(2)
_refine_ls_extinction_coef       0.0015(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     798
_refine_ls_number_reflns         11019
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0701
_refine_ls_R_factor_gt           0.0535
_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^)+(0.0821P)^2^+0.0658P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1420
_refine_ls_wR_factor_ref         0.1530
_reflns_Friedel_coverage         0.918
_reflns_Friedel_fraction_full    0.954
_reflns_Friedel_fraction_max     0.895
_reflns_number_gt                8563
_reflns_number_total             11019
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc00758e2.cif
_cod_data_source_block           ynrk312
_cod_depositor_comments
'Adding full bibliography for 7134301--7134303.cif.'
_cod_database_code               7134302
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.941
_shelx_estimated_absorpt_t_min   0.861
_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
2.a Aromatic/amide H refined with riding coordinates:
 C48(H48), C49(H49), C51(H51), C50(H50), C46(H46), C24(H24), C79(H79),
 C70(H70), C76(H76), C55(H55), C71(H71), C67(H67), C66(H66), C28(H28), C81(H81),
  C72(H72), C13(H13), C37(H37), C60(H60), C9(H9), C80(H80), C39(H39), C56(H56),
 C74(H74), C25(H25), C4(H4), C58(H58), C16(H16), C32(H32), C75(H75), C38(H38),
 C8(H8), C34(H34), C59(H59), C30(H30), C29(H29), C6(H6), C33(H33), C18(H18),
 C14(H14), C61(H61), C19(H19), C7(H7), C17(H17)
2.b Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C64(H64A,H64B,H64C), C63(H63A,H63B,H63C), C22(H22A,H22B,
 H22C)
;
_shelx_res_checksum              83081
_shelx_hkl_checksum              44023
_olex2_submission_special_instructions 'No special instructions were received'