Single-crystal chiral two-dimensional supramolecular organic frameworks for tunable circularly polarized luminescence
Cui, Jialin; Wang, Hui; Liu, Hui; Yu, Hailong; Wang, Wei; Wang, Yu; Zhao, Yingjie; Chemical Science 16 (2025) 7513–7522; doi:10.1039/D4SC08811E

data_1574186
_publ_section_title
;
 Single-crystal chiral two-dimensional supramolecular organic frameworks
 for tunable circularly polarized luminescence
;
_journal_issue                   17
_journal_name_full               'Chemical Science'
_journal_page_first              7513
_journal_page_last               7522
_journal_paper_doi               10.1039/D4SC08811E
_journal_volume                  16
_journal_year                    2025
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C60 H42 N6 O12, C16 H10, C4 H8 O'
_chemical_formula_sum            'C80 H60 N6 O13'
_chemical_formula_weight         1313.34
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc278k69
_audit_creation_date             2020-12-09
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_audit_update_record
;
2021-02-19 deposited with the CCDC.	2025-03-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 89.9918(11)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   20.1153(3)
_cell_length_b                   24.4281(3)
_cell_length_c                   15.72562(18)
_cell_measurement_reflns_used    17227
_cell_measurement_temperature    220.00(15)
_cell_measurement_theta_max      72.1920
_cell_measurement_theta_min      3.6020
_cell_volume                     7727.23(17)
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (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  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      220.00(15)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.976
_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    -23.00  25.00   0.50    0.80    --  -46.70  19.00 -90.00   96
  2  \w    -16.00  25.00   0.50    0.80    --  -46.70  19.00 -30.00   82
  3  \w    -23.00  28.00   0.50    0.80    --  -46.70  19.00-150.00  102
  4  \w    -22.00  12.00   0.50    0.80    --  -46.70  19.00-180.00   68
  5  \w    -59.00 -27.00   0.50    4.00    --  -99.00  61.00-120.00   64
  6  \w    -76.00 -50.00   0.50    4.00    --  -99.00 117.00 -20.73   52
  7  \w    -90.00 -56.00   0.50    0.80    --  -46.70 134.00  -0.00   68
  8  \w    -96.00 -71.00   0.50    4.00    --  -99.00 134.00  -0.00   50
  9  \w   -107.00 -27.00   0.50    4.00    --  -99.00 110.00  44.90  160
 10  \w    -61.00 -34.00   0.50    0.80    --  -46.70 135.00 178.00   54
 11  \w   -112.00 -70.00   0.50    4.00    --  -99.00 125.00  60.00   84
 12  \w   -109.00 -79.00   0.50    4.00    --  -99.00 117.00 -20.73   60
 13  \w   -111.00 -86.00   0.50    4.00    --  -99.00 125.00 -60.00   50
 14  \w   -119.00 -68.00   0.50    4.00    --  -99.00 135.00 178.00  102
 15  \w    -20.00  27.00   0.50    0.80    --   46.70 -19.00 -90.00   94
 16  \w     62.00 108.00   0.50    4.00    --  103.25 -77.00 -60.00   92
 17  \w     77.00 104.00   0.50    4.00    --  103.25 -94.00-120.00   54
 18  \w     48.00 101.00   0.50    4.00    --  103.25 -94.00 -60.00  106
 19  \w     48.00  75.00   0.50    4.00    --  103.25 -61.00 -90.00   54
 20  \w     31.00  75.00   0.50    4.00    --  103.25 -61.00-120.00   88
 21  \w     33.00  74.00   0.50    4.00    --  103.25 -61.00 -60.00   82
 22  \w     37.00  63.00   0.50    0.80    --   46.70-134.00 -67.00   52
 23  \w     32.00 118.00   0.50    4.00    --  103.25-134.00 -67.00  172
 24  \w     36.00  98.00   0.50    0.80    --   46.70-135.00 112.00  124
 25  \w     83.00 119.00   0.50    4.00    --  103.25-135.00 112.00   72
 26  \w     81.00 109.00   0.50    4.00    --  103.25 -77.00 120.00   56
 27  \w     79.00 106.00   0.50    4.00    --  103.25 -94.00 150.00   54
 28  \w     56.00 104.00   0.50    4.00    --  103.25 -94.00 120.00   96
 29  \w     41.00  80.00   0.50    4.00    --  103.25 -77.00 120.00   78
 30  \w     32.00  73.00   0.50    4.00    --  103.25 -61.00  60.00   82
 31  \w     32.00  75.00   0.50    4.00    --  103.25 -61.00 120.00   86
 32  \w     32.00  98.00   0.50    4.00    --  103.25-125.00 150.00  132
 33  \w     91.00 141.00   0.50    4.00    --  103.25  15.00   0.00  100
 34  \w    126.00 152.00   0.50    4.00    --  103.25  61.00 -90.00   52
 35  \w     95.00 169.00   0.50    4.00    --  103.25  61.00-180.00  148
 36  \w     89.00 115.00   0.50    4.00    --  103.25  61.00 -90.00   52
 37  \w     92.00 122.00   0.50    4.00    --  103.25 134.00  -0.00   60
 38  \w     87.00 162.00   0.50    4.00    --  103.25  61.00  90.00  150
 39  \w    104.00 159.00   0.50    4.00    --  103.25  45.00 120.00  110
 40  \w     75.00 145.00   0.50    4.00    --  103.25 135.00 178.00  140
 41  \w     49.00 115.00   0.50    0.80    --   46.70  77.00-180.00  132
 42  \w   -104.00 -68.00   0.50    0.80    --  -46.70-135.00 112.00   72
 43  \w   -123.00 -78.00   0.50    4.00    --  -99.00-135.00 112.00   90
 44  \w   -118.00 -73.00   0.50    0.80    --  -46.70-134.00 -67.00   90
 45  \w   -142.00-117.00   0.50    4.00    --  -99.00-134.00 -67.00   50
 46  \w   -167.00-106.00   0.50    4.00    --  -99.00 -70.00  42.18  122
 47  \w   -167.00 -85.00   0.50    4.00    --  -99.00 -94.00  60.00  164
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0331984000
_diffrn_orient_matrix_UB_12      -0.0518765000
_diffrn_orient_matrix_UB_13      -0.0361651000
_diffrn_orient_matrix_UB_21      0.0472480000
_diffrn_orient_matrix_UB_22      0.0359033000
_diffrn_orient_matrix_UB_23      -0.0532019000
_diffrn_orient_matrix_UB_31      0.0502869000
_diffrn_orient_matrix_UB_32      0.0004552000
_diffrn_orient_matrix_UB_33      0.0738559000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_av_unetI/netI     0.0274
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            51993
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.952
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.573
_diffrn_reflns_theta_min         2.810
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.633
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69623
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.129
_exptl_crystal_description       plate
_exptl_crystal_F_000             2744
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.284
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details
;
 Flack x determined using 5853 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     938
_refine_ls_number_reflns         15270
_refine_ls_number_restraints     192
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0539
_refine_ls_R_factor_gt           0.0477
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0978P)^2^+1.6812P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1372
_refine_ls_wR_factor_ref         0.1442
_reflns_Friedel_coverage         0.904
_reflns_Friedel_fraction_full    0.988
_reflns_Friedel_fraction_max     0.927
_reflns_number_gt                13684
_reflns_number_total             15270
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc08811e2.cif
_cod_data_source_block           tx3993a_sq
_cod_depositor_comments
'Adding full bibliography for 1574186--1574191.cif.'
_cod_original_cell_volume        7727.24(16)
_cod_database_code               1574186
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         CHNO
_reflns_odcompleteness_completeness 99.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 O13-C80 = O13-C77 = O13A-C80A = O13A-C77A
 1.47 with sigma of 0.01
 C79-C78 = C78-C77 = C80-C79 = C79A-C78A = C78A-C77A = C80A-C79A
 1.54 with sigma of 0.01
 C78A-C80A
 2.5 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C78 \\sim O13 \\sim C77 \\sim C80 \\sim C79 \\sim C77A \\sim O13A \\sim C80A
\\sim C78A \\sim C79A: within 1.7A with sigma of 0.02 and sigma for terminal
atoms of 0.04 within 1.7A
Uanis(C78) \\sim Ueq, Uanis(O13) \\sim Ueq, Uanis(C77) \\sim Ueq, Uanis(C80)
\\sim Ueq, Uanis(C79) \\sim Ueq, Uanis(C77A) \\sim Ueq, Uanis(O13A) \\sim Ueq,
Uanis(C80A) \\sim Ueq, Uanis(C78A) \\sim Ueq, Uanis(C79A) \\sim Ueq: with sigma
of 0.01 and sigma for terminal atoms of 0.02
4. Others
 Sof(O13A)=Sof(C77A)=Sof(H77C)=Sof(H77D)=Sof(C78A)=Sof(H78C)=Sof(H78D)=
 Sof(C79A)=Sof(H79C)=Sof(H79D)=Sof(C80A)=Sof(H80C)=Sof(H80D)=1-FVAR(1)
 Sof(O13)=Sof(C77)=Sof(H77A)=Sof(H77B)=Sof(C78)=Sof(H78A)=Sof(H78B)=Sof(C79)=
 Sof(H79A)=Sof(H79B)=Sof(C80)=Sof(H80A)=Sof(H80B)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C15(H15), C20(H20), C35(H35), C40(H40), C55(H55), C60(H60)
5.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C17(H17A,H17B), C18(H18A,H18B), C19(H19A,H19B), C36(H36A,
 H36B), C37(H37A,H37B), C38(H38A,H38B), C39(H39A,H39B), C56(H56A,H56B),
 C57(H57A,H57B), C58(H58A,H58B), C59(H59A,H59B), C77(H77A,H77B), C78(H78A,H78B),
  C79(H79A,H79B), C80(H80A,H80B), C77A(H77C,H77D), C78A(H78C,H78D), C79A(H79C,
 H79D), C80A(H80C,H80D)
5.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C9(H9), C10(H10), C23(H23), C24(H24), C29(H29), C30(H30),
 C43(H43), C44(H44), C49(H49), C50(H50), C62(H62), C63(H63), C64(H64), C66(H66),
  C67(H67), C69(H69), C70(H70), C71(H71), C73(H73), C74(H74)
;
_shelx_res_checksum              66527
_shelx_fab_checksum              85311
_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 1.374
_oxdiff_exptl_absorpt_empirical_full_min 0.755