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_7134303
_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         '2(C42 H28 O2), C7 H8'
_chemical_formula_sum            'C91 H64 O4'
_chemical_formula_weight         1221.42
_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             2024-01-04
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2025-03-06 deposited with the CCDC.	2025-03-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.2610(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.66020(10)
_cell_length_b                   25.9534(3)
_cell_length_c                   15.6096(2)
_cell_measurement_reflns_used    12867
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      74.94
_cell_measurement_theta_min      5.67
_cell_volume                     3090.24(7)
_computing_cell_refinement       'CrysAlisPro 1.171.40.66a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.66a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.66a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (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_detector_area_resol_mean 5.814
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       \w
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0392
_diffrn_reflns_av_unetI/netI     0.0417
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            38014
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.287
_diffrn_reflns_theta_min         4.439
_exptl_absorpt_coefficient_mu    0.611
_exptl_absorpt_correction_T_max  0.941
_exptl_absorpt_correction_T_min  0.846
_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    1.313
_exptl_crystal_description       needle
_exptl_crystal_F_000             1284
_exptl_crystal_preparation       Luminescent,Luminescent,Luminescent
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: MeOH/Toluene'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.753
_refine_diff_density_min         -0.432
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details
;
 Flack x determined using 4745 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     824
_refine_ls_number_reflns         12388
_refine_ls_number_restraints     11
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0570
_refine_ls_R_factor_gt           0.0521
_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^)+(0.0808P)^2^+0.7399P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1395
_refine_ls_wR_factor_ref         0.1441
_reflns_Friedel_coverage         0.919
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.949
_reflns_number_gt                11198
_reflns_number_total             12388
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc00758e2.cif
_cod_data_source_block           ynrk311
_cod_depositor_comments
'Adding full bibliography for 7134301--7134303.cif.'
_cod_database_code               7134303
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.941
_shelx_estimated_absorpt_t_min   0.862
_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. Restrained distances
 C91-C86
 1.39 with sigma of 0.02
 C89-C90
 1.39 with sigma of 0.02
 C86-C85
 1.54 with sigma of 0.02
 C86-C87
 1.39 with sigma of 0.02
 C90-C91
 1.39 with sigma of 0.02
 C87-C88
 1.39 with sigma of 0.02
 C88-C89
 1.39 with sigma of 0.02
 C92-C93
 1.54 with sigma of 0.02
 C94-C92
 2.5 with sigma of 0.04
 C98-C92
 2.5 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
Uanis(C85) = Uanis(C97) = Uanis(C96) = Uanis(C86) = Uanis(C91) = Uanis(C95) =
Uanis(C90) = Uanis(C94) = Uanis(C89) = Uanis(C88) = Uanis(C87) = Uanis(C98) =
Uanis(C92)
Uanis(C85) = Uanis(C97) = Uanis(C86) = Uanis(C91) = Uanis(C96) = Uanis(C95) =
Uanis(C90) = Uanis(C94) = Uanis(C89) = Uanis(C88) = Uanis(C93) = Uanis(C87) =
Uanis(C98) = Uanis(C92)
4. Others
 Sof(C92)=Sof(H92A)=Sof(H92B)=Sof(H92C)=Sof(C96)=Sof(H96)=Sof(C97)=Sof(H97)=
 Sof(C98)=Sof(H98)=Sof(C93)=Sof(C94)=Sof(H94)=Sof(C95)=Sof(H95)=1-FVAR(1)
 Sof(C86)=Sof(C87)=Sof(H87)=Sof(C88)=Sof(H88)=Sof(C89)=Sof(H89)=Sof(C90)=
 Sof(H90)=Sof(C91)=Sof(H91)=Sof(C85)=Sof(H85A)=Sof(H85B)=Sof(H85C)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C81(H81), C24(H24), C46(H46), C67(H67), C4(H4), C6(H6), C80(H80), C51(H51),
 C39(H39), C8(H8), C66(H66), C7(H7), C25(H25), C79(H79), C28(H28), C29(H29),
 C76(H76), C32(H32), C33(H33), C48(H48), C9(H9), C37(H37), C38(H38), C49(H49),
 C50(H50), C14(H14), C30(H30), C70(H70), C34(H34), C18(H18), C17(H17), C13(H13),
  C16(H16), C58(H58), C71(H71), C72(H72), C19(H19), C75(H75), C61(H61),
 C55(H55), C56(H56), C59(H59), C74(H74), C60(H60), C87(H87), C88(H88), C89(H89),
  C90(H90), C91(H91), C96(H96), C97(H97), C98(H98), C94(H94), C95(H95)
5.b Fitted hexagon refined as free rotating group:
 C86(C87,C88,C89,C90,C91), C96(C97,C98,C93,C94,C95)
5.c Idealised Me refined as rotating group:
 C63(H63A,H63B,H63C), C21(H21A,H21B,H21C), C64(H64A,H64B,H64C), C22(H22A,H22B,
 H22C), C85(H85A,H85B,H85C), C92(H92A,H92B,H92C)
;
_shelx_res_checksum              57963
_shelx_hkl_checksum              98190
_olex2_submission_special_instructions 'No special instructions were received'