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_7711266
_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
'C47.25 H34.75 La2 N3.75 O26, 2.5[H2O], 0.5[C3H7NO]'
_chemical_formula_sum            'C48.75 H43.25 La2 N4.25 O29'
_chemical_formula_weight         1430.44
_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             2022-09-12
_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                89.5480(10)
_cell_angle_beta                 83.4300(10)
_cell_angle_gamma                74.6130(10)
_cell_formula_units_Z            2
_cell_length_a                   10.31370(10)
_cell_length_b                   13.1982(2)
_cell_length_c                   19.8651(2)
_cell_measurement_reflns_used    20287
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      77.4250
_cell_measurement_theta_min      4.0770
_cell_volume                     2589.32(6)
_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 0.998
_diffrn_measured_fraction_theta_max 0.950
_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    -47.00  24.00   0.50    0.47    --  -48.44  47.00  21.00  142
  2  \w   -120.00 -94.00   0.50    0.47    --  -48.44 -47.00-127.00   52
  3  \w     -2.00  25.00   0.50    0.47    --   48.44 -47.00-127.00   54
  4  \w     58.00 109.00   0.50    0.47    --   48.44  47.00  21.00  102
  5  \w   -163.00-121.00   0.50    1.89    --  -91.75 -47.00-127.00   84
  6  \w    -53.00 -28.00   0.50    1.89    --  -91.75  47.00  21.00   50
  7  \w    101.00 178.00   0.50    1.89    --  109.00  47.00  21.00  154
  8  \w    -71.00 -20.00   0.50    0.47    --  -48.44  77.00 -90.00  102
  9  \w   -119.00 -58.00   0.50    0.47    --  -48.44 -38.00 -90.00  122
 10  \w   -121.00 -73.00   0.50    0.47    --  -48.44-125.00-180.00   96
 11  \w    -22.00  21.00   0.50    0.47    --  -48.44  19.00 150.00   86
 12  \w     -8.00  23.00   0.50    0.47    --  -48.44  77.00 -90.00   62
 13  \w     41.00  74.00   0.50    0.47    --   48.44-125.00 -90.00   66
 14  \w   -102.00 -73.00   0.50    1.89    --  -91.75-125.00-150.00   58
 15  \w   -162.00-118.00   0.50    1.89    --  -91.75-125.00-150.00   88
 16  \w   -143.00 -70.00   0.50    1.89    --  -91.75 -77.00 -60.00  146
 17  \w    -61.00 -35.00   0.50    1.89    --  -91.75  57.00-150.00   52
 18  \w   -158.00-115.00   0.50    1.89    --  -91.75 -19.00 120.00   86
 19  \w    -66.00 -40.00   0.50    1.89    --  -91.75  57.00  90.00   52
 20  \w    -74.00 -22.00   0.50    1.89    --  -91.75 125.00  90.00  104
 21  \w    -65.00 -22.00   0.50    1.89    --  -91.75 125.00 150.00   86
 22  \w   -160.00 -86.00   0.50    1.89    --  -91.75 -99.00 -30.00  148
 23  \w     94.00 124.00   0.50    1.89    --  109.00  57.00-150.00   60
 24  \w     95.00 152.00   0.50    1.89    --  109.00 125.00 120.00  114
 25  \w     51.00 101.00   0.50    1.89    --  109.00 -99.00-180.00  100
 26  \w     82.00 112.00   0.50    1.89    --  109.00-125.00  30.00   60
 27  \w     40.00  65.00   0.50    1.89    --  109.00 -57.00 -90.00   50
 28  \w     36.00 101.00   0.50    1.89    --  109.00-125.00 -90.00  130
 29  \w     38.00  64.00   0.50    1.89    --  109.00 -99.00 -60.00   52
 30  \w     41.00 104.00   0.50    1.89    --  109.00-125.00 120.00  126
 31  \w     41.00 112.00   0.50    1.89    --  109.00-125.00 -60.00  142
 32  \w     37.00  63.00   0.50    1.89    --  109.00 -57.00-180.00   52
 33  \w     36.00 112.00   0.50    1.89    --  109.00-125.00-150.00  152
 34  \w     71.00 101.00   0.50    1.89    --  109.00-125.00 150.00   60
 35  \w     96.00 178.00   0.50    1.89    --  109.00  38.00 120.00  164
 36  \w     53.00 104.00   0.50    1.89    --  109.00 -99.00  30.00  102
 37  \w     40.00  65.00   0.50    1.89    --  109.00 -57.00-150.00   50
 38  \w    144.00 169.00   0.50    1.89    --  109.00  57.00-150.00   50
 39  \w     58.00 111.00   0.50    1.89    --  109.00-125.00-180.00  106
 40  \w     37.00  62.00   0.50    1.89    --  109.00 -57.00 -60.00   50
 41  \w     73.00 111.00   0.50    1.89    --  109.00-125.00 -30.00   76
 42  \w     41.00  66.00   0.50    1.89    --  109.00 -57.00   0.00   50
 43  \w     81.00 106.00   0.50    1.89    --  109.00 -99.00 -60.00   50
 44  \w     37.00  62.00   0.50    1.89    --  109.00 -57.00  30.00   50
;
_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  0.0423
_diffrn_reflns_av_unetI/netI     0.0421
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.950
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            34300
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.950
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.684
_diffrn_reflns_theta_min         3.474
_exptl_absorpt_coefficient_mu    13.483
_exptl_absorpt_correction_T_max  0.8
_exptl_absorpt_correction_T_min  0.44192
_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 light brown'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.835
_exptl_crystal_description       block
_exptl_crystal_F_000             1423
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.881
_refine_diff_density_min         -1.445
_refine_diff_density_rms         0.112
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     782
_refine_ls_number_reflns         10456
_refine_ls_number_restraints     3789
_refine_ls_restrained_S_all      310.542
_refine_ls_R_factor_all          0.0431
_refine_ls_R_factor_gt           0.0385
_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^)+(0.0652P)^2^+2.2787P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1064
_refine_ls_wR_factor_ref         0.1098
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9213
_reflns_number_total             10456
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2dt02290g2.cif
_cod_data_source_block           3
_cod_original_cell_volume        2589.32(5)
_cod_database_code               7711266
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.498
_shelx_estimated_absorpt_t_min   0.412
_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, All O(H,H) groups
2. Restrained distances
 C47-N4
 1.3 with sigma of 0.02
 C46-N4
 1.3 with sigma of 0.02
 C46-O22
 1.2 with sigma of 0.02
 N4-C48
 1.3 with sigma of 0.02
 H26B-O27
 2 with sigma of 0.02
 O26A-H26B
 0.8 with sigma of 0.000002
 H27B-H26B
 1.4 with sigma of 0.02
 La2-H25A \\sim La2-H25B
 with sigma of 0.02
 La2-H24A \\sim La2-H24B
 with sigma of 0.02
 La1-H21A \\sim La1-H21B
 with sigma of 0.02
 La2-H27A \\sim La2-H27B
 with sigma of 0.02
3. Restrained planarity
 O14, N1, C21, O13, C22, C16, C17, C18, C19, C20, C11, C12, C13, C14, C15, C9A,
  N2, O11B, O12B
 with sigma of 0.01
4. Uiso/Uaniso restraints and constraints
O22: within 1.7A with sigma of 0.04 and sigma for terminal atoms of 0.08 within
1.7A
All non-hydrogen atoms have similar U: within 3.8A with sigma of 0.01 and sigma
for terminal atoms of 0.02 within 3.8A
Uanis(La1) \\sim Ueq, Uanis(O7) \\sim Ueq, Uanis(O8) \\sim Ueq, Uanis(O1) \\sim
Ueq, Uanis(O20) \\sim Ueq, Uanis(O19) \\sim Ueq, Uanis(O21) \\sim Ueq,
Uanis(C1) \\sim Ueq, Uanis(C31) \\sim Ueq, Uanis(C2) \\sim Ueq, Uanis(O2) \\sim
Ueq, Uanis(C32) \\sim Ueq, Uanis(C3) \\sim Ueq, Uanis(C7) \\sim Ueq, Uanis(C33)
\\sim Ueq, Uanis(C37) \\sim Ueq, Uanis(C4) \\sim Ueq, Uanis(C6) \\sim Ueq,
Uanis(C34) \\sim Ueq, Uanis(C36) \\sim Ueq, Uanis(C8) \\sim Ueq, Uanis(C5)
\\sim Ueq, Uanis(N2) \\sim Ueq, Uanis(C35) \\sim Ueq, Uanis(C38) \\sim Ueq,
Uanis(N3) \\sim Ueq, Uanis(O9) \\sim Ueq, Uanis(O10) \\sim Ueq, Uanis(C9A)
\\sim Ueq, Uanis(C10B) \\sim Ueq, Uanis(O3) \\sim Ueq, Uanis(O4) \\sim Ueq,
Uanis(C39) \\sim Ueq, Uanis(C40) \\sim Ueq, Uanis(O12B) \\sim Ueq, Uanis(C13)
\\sim Ueq, Uanis(O11B) \\sim Ueq, Uanis(C11) \\sim Ueq, Uanis(O6) \\sim Ueq,
Uanis(C44) \\sim Ueq, Uanis(O5) \\sim Ueq, Uanis(C41) \\sim Ueq, Uanis(C12)
\\sim Ueq, Uanis(C14) \\sim Ueq, Uanis(C20) \\sim Ueq, Uanis(C43) \\sim Ueq,
Uanis(C45) \\sim Ueq, Uanis(C42) \\sim Ueq, Uanis(C17) \\sim Ueq, Uanis(C15)
\\sim Ueq, Uanis(C19) \\sim Ueq, Uanis(C18) \\sim Ueq, Uanis(C16) \\sim Ueq,
Uanis(C21) \\sim Ueq, Uanis(C22) \\sim Ueq, Uanis(O14) \\sim Ueq, Uanis(N1)
\\sim Ueq, Uanis(O13) \\sim Ueq, Uanis(C23) \\sim Ueq, Uanis(C28) \\sim Ueq,
Uanis(C24) \\sim Ueq, Uanis(C27) \\sim Ueq, Uanis(C25) \\sim Ueq, Uanis(C29)
\\sim Ueq, Uanis(C26) \\sim Ueq, Uanis(C30) \\sim Ueq, Uanis(O17) \\sim Ueq,
Uanis(O18) \\sim Ueq, Uanis(O16) \\sim Ueq, Uanis(O15) \\sim Ueq, Uanis(La2)
\\sim Ueq, Uanis(O26A) \\sim Ueq, Uanis(O25) \\sim Ueq, Uanis(O23) \\sim Ueq,
Uanis(O24) \\sim Ueq, Uanis(O22) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(O22) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C46) \\sim Ueq, Uanis(N4) \\sim Ueq, Uanis(C47) \\sim Ueq, Uanis(O22)
\\sim Ueq, Uanis(La1) \\sim Ueq, Uanis(O7) \\sim Ueq, Uanis(O8) \\sim Ueq,
Uanis(O1) \\sim Ueq, Uanis(O20) \\sim Ueq, Uanis(O19) \\sim Ueq, Uanis(O21)
\\sim Ueq, Uanis(C1) \\sim Ueq, Uanis(C31) \\sim Ueq, Uanis(C2) \\sim Ueq,
Uanis(O2) \\sim Ueq, Uanis(C32) \\sim Ueq, Uanis(C3) \\sim Ueq, Uanis(C7) \\sim
Ueq, Uanis(C33) \\sim Ueq, Uanis(C37) \\sim Ueq, Uanis(C4) \\sim Ueq, Uanis(C6)
\\sim Ueq, Uanis(C34) \\sim Ueq, Uanis(C36) \\sim Ueq, Uanis(C8) \\sim Ueq,
Uanis(C5) \\sim Ueq, Uanis(N2) \\sim Ueq, Uanis(C35) \\sim Ueq, Uanis(C38)
\\sim Ueq, Uanis(N3) \\sim Ueq, Uanis(O9) \\sim Ueq, Uanis(O10) \\sim Ueq,
Uanis(C9A) \\sim Ueq, Uanis(C10B) \\sim Ueq, Uanis(O3) \\sim Ueq, Uanis(O4)
\\sim Ueq, Uanis(C39) \\sim Ueq, Uanis(C40) \\sim Ueq, Uanis(O12B) \\sim Ueq,
Uanis(C13) \\sim Ueq, Uanis(O11B) \\sim Ueq, Uanis(C11) \\sim Ueq, Uanis(O6)
\\sim Ueq, Uanis(C44) \\sim Ueq, Uanis(O5) \\sim Ueq, Uanis(C41) \\sim Ueq,
Uanis(C12) \\sim Ueq, Uanis(C14) \\sim Ueq, Uanis(C20) \\sim Ueq, Uanis(C43)
\\sim Ueq, Uanis(C45) \\sim Ueq, Uanis(C42) \\sim Ueq, Uanis(C17) \\sim Ueq,
Uanis(C15) \\sim Ueq, Uanis(C19) \\sim Ueq, Uanis(C18) \\sim Ueq, Uanis(C16)
\\sim Ueq, Uanis(C21) \\sim Ueq, Uanis(C22) \\sim Ueq, Uanis(O14) \\sim Ueq,
Uanis(N1) \\sim Ueq, Uanis(O13) \\sim Ueq, Uanis(C23) \\sim Ueq, Uanis(C28)
\\sim Ueq, Uanis(C24) \\sim Ueq, Uanis(C27) \\sim Ueq, Uanis(C25) \\sim Ueq,
Uanis(C29) \\sim Ueq, Uanis(C26) \\sim Ueq, Uanis(C30) \\sim Ueq, Uanis(O17)
\\sim Ueq, Uanis(O18) \\sim Ueq, Uanis(O16) \\sim Ueq, Uanis(O15) \\sim Ueq,
Uanis(La2) \\sim Ueq, Uanis(O25) \\sim Ueq, Uanis(O23) \\sim Ueq, Uanis(O26A)
\\sim Ueq, Uanis(O24) \\sim Ueq: with sigma of 0.01 and sigma for terminal
atoms of 0.02
Uanis(C47) \\sim Ueq, Uanis(N4) \\sim Ueq, Uanis(C48) \\sim Ueq, Uanis(C46)
\\sim Ueq, Uanis(O22) \\sim Ueq: with sigma of 0.01 and sigma for terminal
atoms of 0.02
Uanis(C47) \\sim Ueq, Uanis(N4) \\sim Ueq, Uanis(C48) \\sim Ueq: with sigma of
0.01 and sigma for terminal atoms of 0.02
5. Rigid body (RIGU) restrains
 O22, La2
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 La1, O1, O8, O19, O20, O7, O21, C1, C31, C2, O2, C32, C7, C3, C6, C37, C36,
 C33, C4, N2, C5, N3, C35, C34, C8, C9A, C10B, C39, C40, C38, O9, O10, C13,
 O12B, O11B, C11, C44, O6, C41, O5, O3, O4, C12, C14, C20, C43, C45, C42, C17,
 C15, C19, C18, C16, C21, C22, N1, O14, O13, C23, C28, C24, C27, C25, C29, C26,
 C30, O17, O18, La2, O16, O15, O25, O23, O24, O22
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 O26A, La1, O7, O8, O1, O20, O19, O21, C1, C31, C2, O2, C32, C3, C7, C33, C37,
 C4, C6, C34, C36, C8, C5, N2, C35, C38, N3, O9, O10, C9A, C10B, O3, O4, C39,
 C40, O12B, C13, O11B, C11, O6, C44, O5, C41, C12, C14, C20, C43, C45, C42, C17,
  C15, C19, C18, C16, C21, C22, O14, N1, O13, C23, C28, C24, C27, C25, C29, C26,
  C30, O17, O18, O16, O15, La2, O25, O23, O24, O22
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 O22
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 La1, O7, O8, O1, O20, O19, O21, C1, C31, C2, O2, C32, C3, C7, C33, C37, C4,
 C6, C34, C36, C8, C5, N2, C35, C38, N3, O9, O10, C9A, C10B, O3, O4, C39, C40,
 O12B, C13, O11B, C11, O6, C44, O5, C41, C12, C14, C20, C43, C45, C42, C17, C15,
  C19, C18, C16, C21, C22, O14, N1, O13, C23, C28, C24, C27, C25, C29, C26, C30,
  O17, O18, O16, O15, La2, O25, O23, O26A, O24, O22, C46, N4, C47
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 C48, N4, C47, C46, O22
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
6. Others
 Fixed Sof: O12B(0.5) O11B(0.5) C10B(0.5) C9A(0.5) O22(0.75) O26A(0.5)
 H26A(0.5) H26B(0.5) N4(0.75) C47(0.75) H47A(0.75) H47B(0.75) H47C(0.75)
 C46(0.75) H46(0.75) O26B(0.5) H26C(0.5) H26D(0.5) C48(0.75) H48B(0.75)
 H48A(0.75) H48C(0.75) O11A(0.5) O12A(0.5) C9B(0.5) C10A(0.5) O27(0.25)
 H27A(0.25) H27B(0.25)
7.a Free rotating group:
 O25(H25A,H25B), O24(H24A,H24B), O21(H21A,H21B), O27(H27A,H27B)
7.b Rotating group:
 O20(H20A,H20B), O19(H19A,H19B), O23(H23A,H23B), O26A(H26A,H26B), O26B(H26C,
 H26D)
7.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C35(H35), C26(H26), C28(H28), C5(H5), C33(H33), C7(H7), C24(H24),
 C37(H37), C20(H20), C15(H15), C45(H45), C19(H19), C42(H42), C14(H14), C46(H46)
7.d Fitted hexagon refined as free rotating group:
 C10B(N2,C9A,C13,C12,C11)
7.e Idealised Me refined as rotating group:
 C47(H47A,H47B,H47C), C48(H48B,H48A,H48C)
;
_smtbx_masks_special_details
;
A solvent mask was calculated and 96 electrons were 
found in a volume of 320\%A^3^ in 1 void per unit cell. 
This is consistent with the presence of 
2.5[H2O], 0.5[C3H7NO] per Asymmetric Unit 
which account for 90 electrons 
per unit cell.
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              85182
_shelx_hkl_checksum              91996
_shelx_fab_checksum              98753
_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
;