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_7134301
_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, C4 H8 O2'
_chemical_formula_sum            'C46 H36 O4'
_chemical_formula_weight         652.75
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_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                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.62290(10)
_cell_length_b                   15.14060(10)
_cell_length_c                   22.4142(2)
_cell_measurement_reflns_used    14630
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      74.98
_cell_measurement_theta_min      4.91
_cell_volume                     3265.67(5)
_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 0.999
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0292
_diffrn_reflns_av_unetI/netI     0.0268
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            22792
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.325
_diffrn_reflns_theta_min         4.910
_exptl_absorpt_coefficient_mu    0.658
_exptl_absorpt_correction_T_max  0.936
_exptl_absorpt_correction_T_min  0.853
_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    1.328
_exptl_crystal_description       block
_exptl_crystal_F_000             1376
_exptl_crystal_preparation       Luminescent,Luminescent,Luminescent
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: MeOH/1,4-Dioxane'
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.353
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details
;
 Flack x determined using 2546 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.10(8)
_refine_ls_extinction_coef       0.00105(17)
_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   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     454
_refine_ls_number_reflns         6550
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0381
_refine_ls_R_factor_gt           0.0360
_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^)+(0.0513P)^2^+0.5367P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0945
_refine_ls_wR_factor_ref         0.0966
_reflns_Friedel_coverage         0.758
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.956
_reflns_number_gt                6197
_reflns_number_total             6550
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc00758e2.cif
_cod_data_source_block           ynrk316
_cod_depositor_comments
'Adding full bibliography for 7134301--7134303.cif.'
_cod_database_code               7134301
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.955
_shelx_estimated_absorpt_t_min   0.853
_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 C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C46(H46A,H46B), C45(H45A,H45B), C44(H44A,H44B), C43(H43A,H43B)
2.b Aromatic/amide H refined with riding coordinates:
 C13(H13), C4(H4), C9(H9), C19(H19), C6(H6), C8(H8), C14(H14), C7(H7),
 C39(H39), C24(H24), C18(H18), C17(H17), C25(H25), C16(H16), C34(H34), C38(H38),
  C32(H32), C37(H37), C30(H30), C28(H28), C33(H33), C29(H29)
2.c Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C22(H22A,H22B,H22C)
;
_shelx_res_checksum              80654
_shelx_hkl_checksum              79579
_olex2_submission_special_instructions 'No special instructions were received'