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_1574190
_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
'2(C20 H14 N2 O4), C H2 Cl2, C16 H10, 3.88[CH2Cl2]'
_chemical_formula_sum            'C57 H40 Cl2 N4 O8'
_chemical_formula_weight         979.83
_space_group_crystal_system      trigonal
_space_group_IT_number           146
_space_group_name_Hall           'R 3'
_space_group_name_H-M_alt        'R 3 :H'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2024-09-23
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2024-10-15 deposited with the CCDC.	2025-03-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            9
_cell_length_a                   24.6536(8)
_cell_length_b                   24.6536(8)
_cell_length_c                   25.2258(12)
_cell_measurement_reflns_used    9907
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.776
_cell_measurement_theta_min      2.422
_cell_volume                     13278.1(9)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       'Bruker SMART APEX II diffractometer'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector                 'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0979
_diffrn_reflns_av_unetI/netI     0.0685
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            83542
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.868
_diffrn_reflns_theta_min         1.875
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_target            Mo
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.161
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6518
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1294 before and 0.0728 after correction.
The Ratio of minimum to maximum transmission is 0.8742.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.103
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             4572
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details
;
 Flack x determined using 3438 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.24(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     813
_refine_ls_number_reflns         13557
_refine_ls_number_restraints     1073
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0930
_refine_ls_R_factor_gt           0.0558
_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^)+(0.0857P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1450
_refine_ls_wR_factor_ref         0.1607
_reflns_Friedel_coverage         0.946
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.936
_reflns_number_gt                8828
_reflns_number_total             13557
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc08811e2.cif
_cod_data_source_block           cjlc
_cod_depositor_comments
'Adding full bibliography for 1574186--1574191.cif.'
_cod_original_cell_volume        13278.1(11)
_cod_original_sg_symbol_H-M      'R 3'
_cod_database_code               1574190
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_max   0.984
_shelx_estimated_absorpt_t_min   0.976
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 Cl2-C59 = Cl2A-C59A = Cl1A-C59A = Cl1-C59
 1.79 with sigma of 0.01
 C51-C50 = C52-C51 = C53-C52 = C55-C54 = C54-C53 = C54-C41
 1.39 with sigma of 0.01
 C44-C43 = C45-C44 = C46-C45 = C47-C46
 1.39 with sigma of 0.01
 Cl1-Cl2 = Cl2A-Cl1A
 2.924 with sigma of 0.02
3. Restrained planarity
 C42A, C43A, C50A, C51A, C53A, C54A, C55A, C56A, C52A, C41A, C47A, C48A, C49A,
 C44A, C45A, C46A
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.01 and sigma
for terminal atoms of 0.02 within 2A
5. Same fragment restrains
{C41A, C42A, C43A, C44A, C45A, C46A, C47A, C48A, C49A, C50A, C51A, C52A, C53A,
C54A, C55A, C56A} sigma for 1-2: 0.01, 1-3: 0.02
as in
{C41, C42, C43, C44, C45, C46, C47, C48, C49, C50, C51, C52, C53, C54, C55, C56}
6. Others
 Sof(C41A)=Sof(H41A)=Sof(C42A)=Sof(H42A)=Sof(C43A)=Sof(C44A)=Sof(H44A)=
 Sof(C45A)=Sof(H45A)=Sof(C46A)=Sof(H46A)=Sof(C47A)=Sof(C48A)=Sof(H48A)=
 Sof(C49A)=Sof(H49A)=Sof(C50A)=Sof(C51A)=Sof(H51A)=Sof(C52A)=Sof(H52A)=
 Sof(C53A)=Sof(H53A)=Sof(C54A)=Sof(C55A)=Sof(C56A)=1-FVAR(1)
 Sof(C41)=Sof(H41)=Sof(C42)=Sof(H42)=Sof(C43)=Sof(C44)=Sof(H44)=Sof(C45)=
 Sof(H45)=Sof(C46)=Sof(H46)=Sof(C47)=Sof(C48)=Sof(H48)=Sof(C49)=Sof(H49)=
 Sof(C50)=Sof(C51)=Sof(H51)=Sof(C52)=Sof(H52)=Sof(C53)=Sof(H53)=Sof(C54)=
 Sof(C55)=Sof(C56)=FVAR(1)
 Sof(Cl2A)=Sof(C59A)=Sof(H59C)=Sof(H59D)=Sof(Cl1A)=1-FVAR(2)
 Sof(C59)=Sof(H59A)=Sof(H59B)=Sof(Cl1)=Sof(Cl2)=FVAR(2)
7.a Ternary CH refined with riding coordinates:
 C1(H1), C2(H2), C21(H21), C22(H22)
7.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B), C59(H59A,H59B), C23(H23A,
 H23B), C24(H24A,H24B), C25(H25A,H25B), C26(H26A,H26B), C59A(H59C,H59D)
7.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C15(H15), C16(H16), C29(H29), C30(H30), C35(H35), C36(H36),
 C41(H41), C42(H42), C44(H44), C45(H45), C46(H46), C48(H48), C49(H49), C51(H51),
  C52(H52), C53(H53), C41A(H41A), C42A(H42A), C44A(H44A), C45A(H45A),
 C46A(H46A), C48A(H48A), C49A(H49A), C51A(H51A), C52A(H52A), C53A(H53A)
;
_smtbx_masks_special_details
;
A solvent mask was calculated and 1465 electrons were 
found in a volume of 4334\%A^3^ in 1 void per unit cell. 
This is consistent with the presence of 
3.88[CH2Cl2] per Asymmetric Unit 
which account for 1467 electrons 
per unit cell.
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              56563
_shelx_fab_checksum              81348
_olex2_submission_special_instructions 'No special instructions were received'