A series of naphthalenediimide-based metal−organic frameworks: synthesis, photochromism and inkless and erasable printing
Zhong, Xiao-Feng; Luo, Guo-Jun; Li, Wen-Bin; Chen, Xiong-Hai; Wu, Ying; Chen, Yi-Hui; Ye, Jia-Wen; Bai, Jie; Mo, Zong-Wen; Chen, Xiao-Ming; Dalton Transactions  (2022) –; doi:10.1039/D2DT02290G

data_7711265
_publ_section_title
;
 A series of naphthalenediimide-based metal&#x2212;organic frameworks:
 synthesis, photochromism and inkless and erasable printing
;
_journal_name_full               'Dalton Transactions'
_journal_paper_doi               10.1039/D2DT02290G
_journal_year                    2022
_chemical_formula_moiety         'C72 H52 La2 N8 O29, 2(C3 H7 N O)'
_chemical_formula_sum            'C78 H66 La2 N10 O31'
_chemical_formula_weight         1917.22
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2022-09-13
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2022-09-13 deposited with the CCDC.	2022-09-16 downloaded from the CCDC.
;
_cell_angle_alpha                104.480(2)
_cell_angle_beta                 97.442(2)
_cell_angle_gamma                95.258(2)
_cell_formula_units_Z            2
_cell_length_a                   14.8023(4)
_cell_length_b                   15.7594(4)
_cell_length_c                   18.6831(4)
_cell_measurement_reflns_used    30291
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      77.4340
_cell_measurement_theta_min      3.8920
_cell_volume                     4149.26(18)
_computing_cell_refinement       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_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    'olex2.solve 1.3 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.944
_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     98.00 123.00   0.50    0.54    --  109.00  38.00-120.00   50
  2  \w    127.00 175.00   0.50    0.54    --  109.00  38.00-120.00   96
  3  \w    148.00 178.00   0.50    0.54    --  109.00  38.00 -30.00   60
  4  \w    100.00 138.00   0.50    0.54    --  109.00  38.00 -30.00   76
  5  \w     98.00 164.00   0.50    0.54    --  109.00  19.00  90.00  132
  6  \w     36.00  68.00   0.50    0.13    --   48.44 -77.00 120.00   64
  7  \w      1.00  28.00   0.50    0.13    --   48.44 -77.00 120.00   54
  8  \w    -20.00  43.00   0.50    0.13    --   48.44 -38.00  30.00  126
  9  \w     79.00 112.00   0.50    0.54    --  109.00-125.00  30.00   66
 10  \w     85.00 112.00   0.50    0.54    --  109.00-125.00   0.00   54
 11  \w     45.00  70.00   0.50    0.54    --  109.00-125.00  30.00   50
 12  \w     39.00  65.00   0.50    0.54    --  109.00-125.00   0.00   52
 13  \w     83.00 108.00   0.50    0.54    --  109.00-114.00 -98.00   50
 14  \w     37.00 106.00   0.50    0.54    --  109.00-125.00-120.00  138
 15  \w     27.00  82.00   0.50    0.13    --   48.44-114.00 -98.00  110
 16  \w     41.00 107.00   0.50    0.54    --  109.00-108.00  85.20  132
 17  \w     56.00 104.00   0.50    0.54    --  109.00 -99.00  90.00   96
 18  \w     71.00 106.00   0.50    0.54    --  109.00 -99.00 150.00   70
 19  \w     81.00 106.00   0.50    0.54    --  109.00 -99.00 120.00   50
 20  \w     36.00  76.00   0.50    0.54    --  109.00 -99.00 120.00   80
 21  \w     38.00  93.00   0.50    0.54    --  109.00 -99.00 -60.00  110
 22  \w     81.00 106.00   0.50    0.54    --  109.00 -99.00-150.00   50
 23  \w     78.00 105.00   0.50    0.54    --  109.00 -77.00-150.00   54
 24  \w     38.00  65.00   0.50    0.54    --  109.00 -57.00-150.00   54
 25  \w     37.00  62.00   0.50    0.54    --  109.00 -57.00-120.00   50
 26  \w     73.00 105.00   0.50    0.54    --  109.00 -77.00 -90.00   64
 27  \w     40.00  66.00   0.50    0.54    --  109.00 -57.00  90.00   52
 28  \w     37.00  65.00   0.50    0.54    --  109.00 -57.00 120.00   56
 29  \w     38.00  65.00   0.50    0.54    --  109.00 -57.00 150.00   54
 30  \w    103.00 157.00   0.50    0.54    --  109.00 114.00  -7.00  108
 31  \w     95.00 124.00   0.50    0.54    --  109.00 125.00 -60.00   58
 32  \w    132.00 164.00   0.50    0.54    --  109.00 125.00 -60.00   64
 33  \w     98.00 169.00   0.50    0.54    --  109.00 125.00 150.00  142
 34  \w    -18.00  22.00   0.50    0.13    --  -48.44  19.00 -90.00   80
 35  \w    -23.00  21.00   0.50    0.13    --  -48.44  19.00-120.00   88
 36  \w    -65.00 -26.00   0.50    0.54    --  -91.75  57.00 -90.00   78
 37  \w    -59.00 -19.00   0.50    0.54    --  -91.75  57.00  30.00   80
 38  \w    -75.00 -50.00   0.50    0.54    --  -91.75 114.00  -7.00   50
 39  \w    -48.00 -20.00   0.50    0.54    --  -91.75 125.00 -30.00   56
 40  \w    -71.00  -7.00   0.50    0.13    --  -48.44 114.00  -7.00  128
 41  \w    -45.00 -19.00   0.50    0.54    --  -91.75 125.00  90.00   52
 42  \w   -112.00 -87.00   0.50    0.54    --  -91.75 -38.00  30.00   50
 43  \w   -120.00 -36.00   0.50    0.13    --  -48.44 -38.00  90.00  168
 44  \w   -158.00 -78.00   0.50    0.54    --  -91.75 -57.00 -30.00  160
 45  \w   -163.00-133.00   0.50    0.54    --  -91.75 -77.00 -60.00   60
 46  \w   -121.00 -74.00   0.50    0.54    --  -91.75 -77.00 -60.00   94
 47  \w   -148.00 -80.00   0.50    0.54    --  -91.75-114.00 -98.00  136
 48  \w   -163.00 -81.00   0.50    0.54    --  -91.75-125.00  30.00  164
 49  \w   -117.00 -73.00   0.50    0.13    --  -48.44-125.00  30.00   88
 50  \w   -107.00 -73.00   0.50    0.13    --  -48.44-125.00  60.00   68
 51  \w   -119.00 -93.00   0.50    0.13    --  -48.44-125.00 120.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0660
_diffrn_reflns_av_unetI/netI     0.0554
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.944
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            57474
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.944
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.237
_diffrn_reflns_theta_min         3.601
_exptl_absorpt_coefficient_mu    8.619
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.51325
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.122a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear brown'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.535
_exptl_crystal_description       block
_exptl_crystal_F_000             1932
_exptl_crystal_size_max          0.013
_exptl_crystal_size_mid          0.005
_exptl_crystal_size_min          0.004
_refine_diff_density_max         0.952
_refine_diff_density_min         -2.326
_refine_diff_density_rms         0.104
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1231
_refine_ls_number_reflns         16771
_refine_ls_number_restraints     527
_refine_ls_restrained_S_all      1.146
_refine_ls_R_factor_all          0.0610
_refine_ls_R_factor_gt           0.0523
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0797P)^2^+5.0923P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1406
_refine_ls_wR_factor_ref         0.1480
_reflns_Friedel_coverage         0.000
_reflns_number_gt                14048
_reflns_number_total             16771
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2dt02290g2.cif
_cod_data_source_block           2
_cod_database_code               7711265
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.966
_shelx_estimated_absorpt_t_min   0.896
_olex2_refinement_description
;
1. Restrained distances
 H75A-C75
 0.93 with sigma of 0.002
 N6-C66B
 1.5 with sigma of 0.02
 C64B-C66B
 2.5 with sigma of 0.02
 H10B-O31B
 2 with sigma of 0.02
 C65B-C66B
 2.5 with sigma of 0.02
 C64A-O23
 1.2 with sigma of 0.002
 C64A-C65A = C65A-N6
 2.5 with sigma of 0.02
 C64A-C65A
 2.5 with sigma of 0.002
 N6-C65A
 1.5 with sigma of 0.002
 N6-C66A
 1.5 with sigma of 0.002
 C30B-O3B
 1.28 with sigma of 0.02
 O3B-C30B
 1.28 with sigma of 0.002
 O3A-C30A
 1.25 with sigma of 0.02
 C64B-N6
 1.5 with sigma of 0.02
 C65B-N6
 1.5 with sigma of 0.02
 C64A-N6
 1.5 with sigma of 0.02
 C64B-C65B
 2.5 with sigma of 0.02
 N5-C61
 1.5 with sigma of 0.02
 O4B-C30B
 1.28 with sigma of 0.002
 N9-C73
 1.5 with sigma of 0.002
 O31B-C75
 1.23 with sigma of 0.002
 O31B-H75A
 1.8 with sigma of 0.02
 O31B-N9
 2.4 with sigma of 0.02
 C64B-O23
 1.2 with sigma of 0.004
 C64A-O23 \\sim C64A-N6
 with sigma of 0.02
2. Restrained planarity
 C64B, N6, C65B, C66B
 with sigma of 0.01
 C66A, N6, C64A, C65A
 with sigma of 0.1
 O31B, C75, H75A, N9
 with sigma of 0.001
3. Uiso/Uaniso restraints and constraints
N6 \\sim C65A \\sim C66A \\sim C64A: within 3.8A with sigma of 0.001 and sigma
for terminal atoms of 0.002 within 3.8A
C64A \\sim C64B \\sim N6 \\sim C65A \\sim C65B \\sim C66B \\sim C66A: within
3.8A with sigma of 0.001 and sigma for terminal atoms of 0.002 within 3.8A
C75 \\sim O31A \\sim N9 \\sim O31B \\sim H75 \\sim H75A \\sim C73 \\sim H73A
\\sim C74 \\sim H73B \\sim H73C \\sim H74A \\sim H74B \\sim H74C: within 1.7A
with sigma of 0.04 and sigma for terminal atoms of 0.08 within 1.7A
C72B \\sim C72A \\sim C71A \\sim C71B \\sim N8: within 3.8A with sigma of 0.01
and sigma for terminal atoms of 0.02 within 3.8A
Uanis(C66A) \\sim Ueq, Uanis(C66B) \\sim Ueq, Uanis(N6) \\sim Ueq: with sigma
of 0.001 and sigma for terminal atoms of 0.002
Uanis(N6) \\sim Ueq, Uanis(C65A) \\sim Ueq, Uanis(C65B) \\sim Ueq, Uanis(C64A)
\\sim Ueq, Uanis(C64B) \\sim Ueq, Uanis(C66A) \\sim Ueq, Uanis(C66B) \\sim Ueq:
with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(O31B) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
Uanis(O3B) \\sim Ueq, Uanis(C30B) \\sim Ueq, Uanis(O4B) \\sim Ueq: with sigma
of 0.01 and sigma for terminal atoms of 0.02
Uanis(C70A) \\sim Ueq, Uanis(C70B) \\sim Ueq, Uanis(C71A) \\sim Ueq,
Uanis(C71B) \\sim Ueq, Uanis(C72A) \\sim Ueq, Uanis(C72B) \\sim Ueq: with sigma
of 0.001 and sigma for terminal atoms of 0.002
Uanis(C72B) \\sim Ueq, Uanis(C72A) \\sim Ueq, Uanis(C71B) \\sim Ueq,
Uanis(C71A) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(O3B) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(O3B) \\sim Ueq, Uanis(O3A) \\sim Ueq, Uanis(C30B) \\sim Ueq, Uanis(C30A)
\\sim Ueq, Uanis(O4B) \\sim Ueq, Uanis(O4A) \\sim Ueq: with sigma of 0.01 and
sigma for terminal atoms of 0.02
Uanis(N9) \\sim Ueq, Uanis(O31A) \\sim Ueq, Uanis(C73) \\sim Ueq, Uanis(C74)
\\sim Ueq: with sigma of 0.1 and sigma for terminal atoms of 0.2
Uanis(O31A) \\sim Ueq, Uanis(N9) \\sim Ueq, Uanis(C73) \\sim Ueq, Uanis(C74)
\\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C8) \\sim Ueq, Uanis(C1A) \\sim Ueq, Uanis(O10A) \\sim Ueq, Uanis(O10B)
\\sim Ueq, Uanis(O9B) \\sim Ueq, Uanis(O9A) \\sim Ueq, Uanis(C1B) \\sim Ueq:
with sigma of 0.001 and sigma for terminal atoms of 0.002
4. Rigid body (RIGU) restrains
 C75, O31B
 with sigma for 1-2 distances of 0.00001 and sigma for 1-3 distances of 0.00001
 C75, O31A, N9, O31B, C73, C74, H73A, H73B, H73C, H74A, H74B, H74C
 with sigma for 1-2 distances of 0.0001 and sigma for 1-3 distances of 0.0002
 C71B, C71A, C70B, C70A, C72B, C72A
 with sigma for 1-2 distances of 0.0001 and sigma for 1-3 distances of 0.0002
5. Others
 Sof(C64B)=Sof(H64B)=Sof(C66B)=Sof(H66D)=Sof(H66E)=Sof(H66F)=Sof(C65B)=
 Sof(H65D)=Sof(H65E)=Sof(H65F)=1-FVAR(1)
 Sof(C64A)=Sof(H64A)=Sof(C65A)=Sof(H65A)=Sof(H65B)=Sof(H65C)=Sof(C66A)=
 Sof(H66A)=Sof(H66B)=Sof(H66C)=FVAR(1)
 Sof(O10A)=Sof(C1A)=Sof(O9A)=Sof(H9A)=1-FVAR(2)
 Sof(O10B)=Sof(H10B)=Sof(O9B)=Sof(C1B)=FVAR(2)
 Fixed Sof: O4B(0.5) H4B(0.5) O3B(0.5) C30B(0.5) C70B(0.5) H70B(0.5) C70A(0.5)
 H70A(0.5) C71B(0.5) H71A(0.5) H71B(0.5) H71C(0.5) C72B(0.5) H72A(0.5)
 H72B(0.5) H72C(0.5) C72A(0.5) H72D(0.5) H72E(0.5) H72F(0.5) C71A(0.5)
 H71D(0.5) H71E(0.5) H71F(0.5) C30A(0.5) O3A(0.5) O4A(0.5) H4A(0.5) O31A(0.75)
 O31B(0.25) H75(0.75) H75A(0.25)
6.a Riding coordinates:
 C72A(H72D,H72E,H72F), C71A(H71D,H71E,H71F), C66B(H66D,H66E,H66F), C75(H75)
6.b Rotating group:
 O22(H22A,H22B)
6.c Aromatic/amide H refined with riding coordinates:
 C38(H38), C33(H33), C56(H56), C5(H5), C58(H58), C28(H28), C54(H54), C36(H36),
 C15(H15), C45(H45), C19(H19), C2(H2), C20(H20), C50(H50), C44(H44), C14(H14),
 C49(H49), C7(H7), C26(H26), C24(H24), C67(H67), C61(H61), C76(H76), C70B(H70B),
  C70A(H70A), C64A(H64A), C64B(H64B)
6.d Idealised Me refined as rotating group:
 C77(H77A,H77B,H77C), C62(H62A,H62B,H62C), C78(H78A,H78B,H78C), C68(H68A,H68B,
 H68C), C63(H63A,H63B,H63C), C69(H69A,H69B,H69C), C71B(H71A,H71B,H71C),
 C72B(H72A,H72B,H72C), C65A(H65A,H65B,H65C), C66A(H66A,H66B,H66C), C73(H73A,
 H73B,H73C), C74(H74A,H74B,H74C), C65B(H65D,H65E,H65F)
6.e Idealised tetrahedral OH refined as rotating group:
 O4B(H4B), O10B(H10B), O4A(H4A), O9A(H9A)
;
_shelx_res_checksum              11452
_shelx_hkl_checksum              17914
_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
;