Wavelength-dependent tri-state photoswitching in crystals <i>via</i> synergistic dimer confinement and charge-transfer stacking.
Huang, Zhi; Wei, Jianwei; Wang, Xiang-Yu; Xu, Shaojie; Huang, Ling; Zeng, Le; Materials horizons 12 (2025) 9079–9086; doi:10.1039/d5mh01024a

data_1575190
_publ_section_title
;
 Wavelength-dependent tri-state photoswitching in crystals <i>via</i>
 synergistic dimer confinement and charge-transfer stacking.
;
_journal_issue                   21
_journal_name_full               'Materials horizons'
_journal_page_first              9079
_journal_page_last               9086
_journal_paper_doi               10.1039/d5mh01024a
_journal_volume                  12
_journal_year                    2025
_chemical_formula_moiety         'C75 H61.674 Ca4 N9 O29.481, C14 H10'
_chemical_formula_sum            'C89 H71.67 Ca4 N9 O29.48'
_chemical_formula_weight         1899.24
_chemical_name_common            Ca-NDI@An
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2025-01-06
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2025-01-22 deposited with the CCDC.	2025-07-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 125.5490(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   41.8161(5)
_cell_length_b                   10.36690(10)
_cell_length_c                   24.5777(3)
_cell_measurement_reflns_used    24392
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      76.0330
_cell_measurement_theta_min      2.5980
_cell_volume                     8668.7(2)
_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      293(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0333
_diffrn_reflns_av_unetI/netI     0.0406
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       49
_diffrn_reflns_limit_h_min       -49
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            27344
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        66.592
_diffrn_reflns_theta_max         66.592
_diffrn_reflns_theta_min         2.209
_exptl_absorpt_coefficient_mu    2.942
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.48996
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            orange-red
_exptl_crystal_density_diffrn    1.455
_exptl_crystal_description       rod
_exptl_crystal_F_000             3938
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.731
_refine_diff_density_min         -0.904
_refine_diff_density_rms         0.095
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     834
_refine_ls_number_reflns         7599
_refine_ls_number_restraints     2302
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0844
_refine_ls_R_factor_gt           0.0787
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1501P)^2^+23.3884P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2293
_refine_ls_wR_factor_ref         0.2374
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6789
_reflns_number_total             7599
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5mh01024a2.cif
_cod_data_source_block           1
_cod_depositor_comments
'Adding full bibliography for 1575190--1575191.cif.'
_cod_original_cell_volume        8668.71(19)
_cod_database_code               1575190
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.9982(4)
 0.0018(4)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
3. Restrained distances
 N37-C36 = N37-C38 = N37-C39
 1.47 with sigma of 0.02
 C7G-C1G = C14G-C8G = C7G-C9G = C14G-C2G
 1.39 with sigma of 0.02
 N5-C17 \\sim N5-C16 \\sim N5-C1A
 with sigma of 0.02
 C16-C17 \\sim C17-C1A \\sim C1A-C16
 with sigma of 0.02
 N4-C18 \\sim N4-C20 \\sim N4-C19
 with sigma of 0.02
 C18-C19 \\sim C18-C20 \\sim C19-C20
 with sigma of 0.02
 N6-C35 \\sim N6-C44 \\sim N6-C37
 with sigma of 0.02
 C36-C38 \\sim C36-C39 \\sim C38-C39
 with sigma of 0.02
4. Restrained planarity
 O12, C17, N5, C1A, C16
 with sigma of 0.1
 N6, C35, O10, C37, C44
 with sigma of 0.1
 O10, N4, C18, C19, C20
 with sigma of 0.05
 C39, O35, C36, N37, C38
 with sigma of 0.1
 N4, C20, C19, C18, O10
 with sigma of 0.1
 C14G, C13G, C12G, C11G, C10G, C9G, C8G, C7G, C6G, C5G, C4G, C3G, C2G, C1G
 with sigma of 0.1
5. Uiso/Uaniso restraints and constraints
C23 \\sim C11 \\sim C24 \\sim C4 \\sim C3 \\sim C2 \\sim C7 \\sim C27 \\sim C1
\\sim C22 \\sim C31 \\sim C12 \\sim C8 \\sim C5 \\sim C32 \\sim C21 \\sim C10
\\sim C6 \\sim C29 \\sim C33 \\sim C14 \\sim C28 \\sim C26 \\sim C25 \\sim C30
\\sim C9 \\sim C34 \\sim C13 \\sim C41 \\sim C42 \\sim C43 \\sim C15 \\sim C40
\\sim C39 \\sim C36 \\sim C38 \\sim C18 \\sim C19 \\sim C20 \\sim C14G \\sim
C13G \\sim C12G \\sim C11G \\sim C10G \\sim C9G \\sim C8G \\sim C7G \\sim C6G
\\sim C5G \\sim C4G \\sim C3G \\sim C2G \\sim C1G \\sim C16 \\sim C17 \\sim C1A
\\sim C35 \\sim C37 \\sim C44 \\sim C1B \\sim C1C \\sim C1D \\sim N1 \\sim N2
\\sim N3 \\sim N37 \\sim N4 \\sim N5 \\sim N6 \\sim N7 \\sim O13 \\sim O9 \\sim
O7 \\sim O1 \\sim O2 \\sim O5 \\sim O8 \\sim O14 \\sim O4 \\sim O6 \\sim O15
\\sim O18 \\sim O20 \\sim O3 \\sim O90 \\sim O30 \\sim O35 \\sim O10 \\sim O12
\\sim O16 \\sim O11: within 3A with sigma of 0.02 and sigma for terminal atoms
of 0.04 within 3A
Uanis(O13) \\sim Ueq, Uanis(O9) \\sim Ueq, Uanis(O7) \\sim Ueq, Uanis(O1) \\sim
Ueq, Uanis(O2) \\sim Ueq, Uanis(O5) \\sim Ueq, Uanis(O8) \\sim Ueq, Uanis(O14)
\\sim Ueq, Uanis(O4) \\sim Ueq, Uanis(O6) \\sim Ueq, Uanis(O15) \\sim Ueq,
Uanis(O18) \\sim Ueq, Uanis(O20) \\sim Ueq, Uanis(O3) \\sim Ueq, Uanis(O90)
\\sim Ueq, Uanis(O30) \\sim Ueq, Uanis(O35) \\sim Ueq, Uanis(O10) \\sim Ueq,
Uanis(O12) \\sim Ueq, Uanis(O16) \\sim Ueq, Uanis(O11) \\sim Ueq: with sigma of
0.01 and sigma for terminal atoms of 0.02
Uanis(O35) \\sim Ueq, Uanis(C36) \\sim Ueq, Uanis(N37) \\sim Ueq, Uanis(C39)
\\sim Ueq, Uanis(C38) \\sim Ueq, Uanis(O10) \\sim Ueq, Uanis(C18) \\sim Ueq,
Uanis(N4) \\sim Ueq, Uanis(C19) \\sim Ueq, Uanis(C20) \\sim Ueq, Uanis(O15)
\\sim Ueq, Uanis(C43) \\sim Ueq, Uanis(N3) \\sim Ueq, Uanis(C42) \\sim Ueq,
Uanis(C41) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C14G) \\sim Ueq, Uanis(C13G) \\sim Ueq, Uanis(C12G) \\sim Ueq,
Uanis(C11G) \\sim Ueq, Uanis(C10G) \\sim Ueq, Uanis(C9G) \\sim Ueq, Uanis(C8G)
\\sim Ueq, Uanis(C7G) \\sim Ueq, Uanis(C6G) \\sim Ueq, Uanis(C5G) \\sim Ueq,
Uanis(C4G) \\sim Ueq, Uanis(C3G) \\sim Ueq, Uanis(C2G) \\sim Ueq, Uanis(C1G)
\\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
6. Others
 Sof(O90)=1-FVAR(1)
 Sof(O20)=FVAR(1)
 Sof(N6)=Sof(C35)=Sof(H35)=Sof(C37)=Sof(H37A)=Sof(H37B)=Sof(H37C)=Sof(C44)=
 Sof(H44A)=Sof(H44B)=Sof(H44C)=1-FVAR(2)
 Sof(N4)=Sof(C18)=Sof(H18)=Sof(C19)=Sof(H19A)=Sof(H19B)=Sof(H19C)=Sof(C20)=
 Sof(H20A)=Sof(H20B)=Sof(H20C)=FVAR(2)
 Sof(O30)=1-FVAR(3)
 Sof(O3)=FVAR(3)
 Sof(O4)=Sof(O11)=Sof(H11A)=Sof(H11B)=1-FVAR(4)
 Sof(O14)=FVAR(4)
 Sof(H16A)=Sof(H16B)=Sof(H16C)=Sof(H17)=1-FVAR(5)
 Sof(O12)=Sof(C16)=Sof(C17)=Sof(N5)=Sof(C1A)=Sof(H1AA)=Sof(H1AB)=Sof(H1AC)=0.5*
 (1-FVAR(6))
 Sof(C39)=Sof(O35)=Sof(C36)=Sof(N37)=Sof(C38)=0.5*FVAR(6)
 Sof(H39A)=Sof(H39B)=Sof(H39C)=Sof(H36)=Sof(H38A)=Sof(H38B)=Sof(H38C)=FVAR(5)
 Sof(O16)=Sof(N7)=Sof(C1B)=Sof(H1BA)=Sof(H1BB)=Sof(H1BC)=Sof(C1C)=Sof(H1CA)=
 Sof(H1CB)=Sof(H1CC)=Sof(C1D)=Sof(H1D)=1-FVAR(6)
 Sof(O15)=Sof(N3)=Sof(C41)=Sof(H41A)=Sof(H41B)=Sof(H41C)=Sof(C42)=Sof(H42A)=
 Sof(H42B)=Sof(H42C)=Sof(C43)=Sof(H43)=FVAR(6)
 Fixed Sof: C14G(0.5) H14G(0.5) C13G(0.5) H13G(0.5) C12G(0.5) H12G(0.5)
 C11G(0.5) H11G(0.5) C10G(0.5) H10G(0.5) C9G(0.5) C8G(0.5) C7G(0.5) H7G(0.5)
 C6G(0.5) H6G(0.5) C5G(0.5) H5G(0.5) C4G(0.5) H4G(0.5) C3G(0.5) H3G(0.5)
 C2G(0.5) C1G(0.5)
7.a Rotating group:
 O11(H11A,H11B)
7.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C1(H1), C31(H31), C5(H5), C21(H21), C29(H29), C33(H33), C25(H25),
 C9(H9), C13(H13), C43(H43), C36(H36), C18(H18), C14G(H14G), C13G(H13G),
 C12G(H12G), C11G(H11G), C10G(H10G), C7G(H7G), C6G(H6G), C5G(H5G), C4G(H4G),
 C3G(H3G), C17(H17), C35(H35), C1D(H1D)
7.c Fitted hexagon refined as free rotating group:
 C13G(C12G,C11G,C10G,C9G,C8G), C6G(C5G,C4G,C3G,C2G,C1G)
7.d Idealised Me refined as rotating group:
 C41(H41A,H41B,H41C), C42(H42A,H42B,H42C), C39(H39A,H39B,H39C), C38(H38A,H38B,
 H38C), C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C16(H16A,H16B,H16C), C1A(H1AA,
 H1AB,H1AC), C37(H37A,H37B,H37C), C44(H44A,H44B,H44C), C1B(H1BA,H1BB,H1BC),
 C1C(H1CA,H1CB,H1CC)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              41654
_shelx_fab_checksum              24927
_olex2_submission_special_instructions 'No special instructions were received'