Metal–organic frameworks constructed using acid–base mixed ligands, carboxylic acids and N-containing chalcone, and their catalytic performance for Knoevenagel condensation
Cheng, Limin; Zhang, Junyong; Zhan, Caihong; Xu, Hao; Gong, Chunhua; Xie, Jingli; New Journal of Chemistry 48 (2024) 8597–8602; doi:10.1039/D3NJ05164A

data_7063121
_publ_section_title
;
 Metal--organic frameworks constructed using acid--base mixed ligands,
 carboxylic acids and N-containing chalcone, and their catalytic
 performance for Knoevenagel condensation
;
_journal_issue                   19
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              8597
_journal_page_last               8602
_journal_paper_doi               10.1039/D3NJ05164A
_journal_volume                  48
_journal_year                    2024
_chemical_formula_moiety         'C42 H29 Co N5 O7, 2(C4 H9 N O)'
_chemical_formula_sum            'C50 H47 Co N7 O9'
_chemical_formula_weight         948.87
_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
_audit_creation_date             2024-03-31
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2018.07.26 svn.r3523 for OlexSys, GUI svn.r5532)
;
_audit_update_record
;
2024-03-31 deposited with the CCDC.	2024-04-03 downloaded from the CCDC.
;
_cell_angle_alpha                82.802(3)
_cell_angle_beta                 81.793(3)
_cell_angle_gamma                87.487(3)
_cell_formula_units_Z            2
_cell_length_a                   9.6124(3)
_cell_length_b                   14.9026(5)
_cell_length_c                   17.2025(6)
_cell_measurement_reflns_used    9224
_cell_measurement_temperature    300(2)
_cell_measurement_theta_max      76.3350
_cell_measurement_theta_min      2.5920
_cell_volume                     2418.95(14)
_computing_cell_refinement       'CrysAlisPro 1.171.41.49a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.41.49a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.41.49a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      300.15
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.961
_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     31.00  56.00   0.50    0.10    --   47.82  64.00  87.00   50
  2  \w     72.00 115.00   0.50    0.10    --   47.82  64.00  87.00   86
  3  \w     89.00 171.00   0.50    0.40    --  106.49  64.00  87.00  164
  4  \w     96.00 178.00   0.50    0.40    --  106.49  45.00  30.00  164
  5  \w     96.00 167.00   0.50    0.40    --  106.49  30.00   0.00  142
  6  \w    101.00 131.00   0.50    0.40    --  106.49 125.00 -90.00   60
  7  \w     97.00 125.00   0.50    0.40    --  106.49 125.00-150.00   56
  8  \w    152.00 178.00   0.50    0.40    --  106.49 125.00 -90.00   52
  9  \w    129.00 154.00   0.50    0.40    --  106.49 125.00   0.00   50
 10  \w     95.00 172.00   0.50    0.40    --  106.49  45.00-150.00  154
 11  \w      0.00  27.00   0.50    0.10    --   47.82 -19.00-150.00   54
 12  \w     -2.00  24.00   0.50    0.10    --   47.82 -64.00 -49.00   52
 13  \w     25.00  62.00   0.50    0.10    --   47.82 -64.00 -49.00   74
 14  \w     38.00  96.00   0.50    0.10    --   47.82-125.00 -30.00  116
 15  \w     38.00 111.00   0.50    0.40    --  106.49-125.00 -60.00  146
 16  \w     37.00 108.00   0.50    0.40    --  106.49-112.00 -40.48  142
 17  \w     36.00  63.00   0.50    0.40    --  106.49-106.00 -38.58   54
 18  \w     44.00 110.00   0.50    0.40    --  106.49-125.00-120.00  132
 19  \w     76.00 104.00   0.50    0.40    --  106.49 -94.00 -60.00   56
 20  \w     82.00 107.00   0.50    0.40    --  106.49-106.00 -38.58   50
 21  \w     40.00 105.00   0.50    0.40    --  106.49-125.00-150.00  130
 22  \w     83.00 111.00   0.50    0.40    --  106.49-125.00 -90.00   56
 23  \w     72.00 102.00   0.50    0.40    --  106.49 -94.00   0.00   60
 24  \w     60.00 104.00   0.50    0.40    --  106.49 -94.00  30.00   88
 25  \w     38.00  63.00   0.50    0.40    --  106.49-125.00  30.00   50
 26  \w     35.00 111.00   0.50    0.40    --  106.49-125.00  90.00  152
 27  \w     36.00 108.00   0.50    0.40    --  106.49-113.00 156.41  144
 28  \w     39.00  64.00   0.50    0.40    --  106.49 -61.00 120.00   50
 29  \w     34.00  59.00   0.50    0.40    --  106.49 -61.00  90.00   50
 30  \w     38.00  99.00   0.50    0.40    --  106.49 -77.00  60.00  122
 31  \w     71.00  96.00   0.50    0.40    --  106.49 -77.00  30.00   50
 32  \w     43.00  68.00   0.50    0.40    --  106.49 -77.00  30.00   50
 33  \w     34.00  76.00   0.50    0.40    --  106.49 -64.00 -49.00   84
 34  \w     44.00  71.00   0.50    0.40    --  106.49 -61.00 -30.00   54
 35  \w     78.00 104.00   0.50    0.40    --  106.49-125.00  30.00   52
 36  \w    -64.00  20.00   0.50    0.10    --  -47.82  64.00  87.00  168
 37  \w    -69.00 -44.00   0.50    0.40    --  -86.25  64.00  87.00   50
 38  \w    -51.00 -14.00   0.50    0.40    --  -86.25  45.00  90.00   74
 39  \w    -45.00 -20.00   0.50    0.40    --  -86.25  45.00 -60.00   50
 40  \w    -51.00 -15.00   0.50    0.40    --  -86.25  45.00 -90.00   72
 41  \w    -70.00 -45.00   0.50    0.40    --  -86.25  61.00 -90.00   50
 42  \w    -46.00 -20.00   0.50    0.40    --  -86.25  45.00-150.00   52
 43  \w    -41.00 -14.00   0.50    0.40    --  -86.25  45.00-120.00   54
 44  \w   -157.00 -87.00   0.50    0.40    --  -86.25 -15.00 150.00  140
 45  \w   -140.00 -70.00   0.50    0.40    --  -86.25 -64.00 -49.00  140
 46  \w   -119.00 -30.00   0.50    0.10    --  -47.82 -64.00 -49.00  178
 47  \w   -121.00 -93.00   0.50    0.10    --  -47.82 -19.00-120.00   56
 48  \w   -119.00 -73.00   0.50    0.10    --  -47.82-125.00-120.00   92
 49  \w   -115.00 -84.00   0.50    0.10    --  -47.82-125.00 -90.00   62
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1140553000
_diffrn_orient_matrix_UB_12      0.0710811000
_diffrn_orient_matrix_UB_13      -0.0065606000
_diffrn_orient_matrix_UB_21      0.0402107000
_diffrn_orient_matrix_UB_22      -0.0102560000
_diffrn_orient_matrix_UB_23      -0.0884548000
_diffrn_orient_matrix_UB_31      -0.1077650000
_diffrn_orient_matrix_UB_32      0.0755439000
_diffrn_orient_matrix_UB_33      -0.0209766000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.1540
_diffrn_reflns_av_unetI/netI     0.1429
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            36110
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.876
_diffrn_reflns_theta_min         2.614
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.297
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73932
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.49a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            purple
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_description       block
_exptl_crystal_F_000             990
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.702
_refine_diff_density_min         -0.339
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.997
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     876
_refine_ls_number_reflns         9814
_refine_ls_number_restraints     467
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.1375
_refine_ls_R_factor_gt           0.0731
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.0850P)^2^]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1725
_refine_ls_wR_factor_ref         0.2154
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5324
_reflns_number_total             9814
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3nj05164a2.cif
_cod_data_source_block           3_CCDC1
_cod_depositor_comments
'Adding full bibliography for 7063120--7063122.cif.'
_cod_original_cell_volume        2418.92(15)
_cod_database_code               7063121
_shelxl_version_number           2013-2
_reflns_odcompleteness_completeness 99.73
_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
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 N9-C2AA = N9-C3AA = N9-C0AA
 1.45 with sigma of 0.01
 O0AA-C0AA
 1.2 with sigma of 0.02
 C1AA-C0AA
 1.51 with sigma of 0.01
 N0AA-C6AA = N0AA-C5AA = N0AA-C4AA
 1.45 with sigma of 0.01
 C7AA-C4AA
 1.51 with sigma of 0.01
 O1AA-C4AA
 1.2 with sigma of 0.01
 N1AA-C0BA = N1AA-C1BA = N1AA-C8AA
 1.45 with sigma of 0.01
 C9AA-C8AA
 1.51 with sigma of 0.01
 O2AA-C8AA
 1.2 with sigma of 0.01
 O4-H4 = O3-H3
 0.82 with sigma of 0.02
 N2-C56 \\sim C56-C23 \\sim C26-C23 \\sim C36-C26 \\sim C57-C36 \\sim N2-C57
 with sigma of 0.02
 N1-C60 \\sim N1-C58 \\sim C22-C58 \\sim C29-C22 \\sim C59-C29 \\sim C59-C60
 with sigma of 0.02
3. Restrained planarity
 N2, C23, C26, C36, C56, C57
 with sigma of 0.1
 N1, C22, C29, C58, C59, C60
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
Uanis(C52) \\sim Ueq, Uanis(C45) \\sim Ueq, Uanis(C44) \\sim Ueq, Uanis(C41)
\\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C41) \\sim Ueq, Uanis(C44) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(N2) \\sim Ueq, Uanis(C1) \\sim Ueq, Uanis(C2) \\sim Ueq, Uanis(C3) \\sim
Ueq, Uanis(C4) \\sim Ueq, Uanis(C5) \\sim Ueq, Uanis(C23) \\sim Ueq, Uanis(C26)
\\sim Ueq, Uanis(C36) \\sim Ueq, Uanis(C56) \\sim Ueq, Uanis(C57) \\sim Ueq:
with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C22) \\sim Ueq, Uanis(C29) \\sim Ueq, Uanis(C30) \\sim Ueq, Uanis(C31)
\\sim Ueq, Uanis(C32) \\sim Ueq, Uanis(C33) \\sim Ueq, Uanis(N1) \\sim Ueq,
Uanis(C58) \\sim Ueq, Uanis(C59) \\sim Ueq, Uanis(C60) \\sim Ueq, Uanis(C34)
\\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C51) \\sim Ueq, Uanis(C48) \\sim Ueq, Uanis(O7) \\sim Ueq, Uanis(O8)
\\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C54) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C43) \\sim Ueq, Uanis(C53) \\sim Ueq, Uanis(C50) \\sim Ueq, Uanis(C49)
\\sim Ueq, Uanis(O8) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms
of 0.02
Uanis(N9) \\sim Ueq, Uanis(C3AA) \\sim Ueq, Uanis(O2AA) \\sim Ueq, Uanis(C3BA)
\\sim Ueq, Uanis(C4BA) \\sim Ueq, Uanis(O3AA) \\sim Ueq, Uanis(C2BA) \\sim Ueq:
with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C0AA) \\sim Ueq, Uanis(C2AA) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(C1BA) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
5. Rigid body (RIGU) restrains
 N2, C1, C2, C3, C4, C5, C23, C26, C36, C56, C57
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 N1, C22, C29, C30, C31, C32, C33, C34, C58, C59, C60
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Others
 Sof(C22)=Sof(H22)=Sof(C29)=Sof(C58)=Sof(H58)=Sof(C59)=Sof(H59)=Sof(C60)=
 Sof(H60)=1-FVAR(1)
 Sof(C30)=Sof(H30)=Sof(C31)=Sof(C32)=Sof(H32)=Sof(C33)=Sof(H33)=Sof(C34)=
 Sof(H34)=FVAR(1)
 Fixed Sof: H4(0.5) O7(0.5) O8(0.5) C1(0.5) H1(0.5) C2(0.5) H2(0.5) C3(0.5)
 C4(0.5) H4A(0.5) C5(0.5) H5(0.5) C23(0.5) H23(0.5) C26(0.5) C36(0.5) H36(0.5)
 C40(0.5) C41(0.5) H41(0.5) C42(0.5) C43(0.5) H43A(0.5) H43B(0.5) C44(0.5)
 H44(0.5) C45(0.5) H45A(0.5) H45B(0.5) C46(0.5) C47(0.5) C48(0.5) C49(0.5)
 C50(0.5) H50A(0.5) H50B(0.5) C51(0.5) H51A(0.5) H51B(0.5) C52(0.5) H52A(0.5)
 H52B(0.5) C53(0.5) H53A(0.5) H53B(0.5) C54(0.5) H54(0.5) C55(0.5) H55(0.5)
 C56(0.5) H56(0.5) C57(0.5) H57(0.5) O0AA(0.5) N9(0.5) C0AA(0.5) C3AA(0.5)
 H3AA(0.5) H3AB(0.5) H3AC(0.5) C1AA(0.5) H1AA(0.5) H1AB(0.5) H1AC(0.5)
 C2AA(0.5) H2AA(0.5) H2AB(0.5) H2AC(0.5) O1AA(0.5) N0AA(0.5) C5AA(0.5)
 H5AA(0.5) H5AB(0.5) H5AC(0.5) C4AA(0.5) C6AA(0.5) H6AA(0.5) H6AB(0.5)
 H6AC(0.5) C7AA(0.5) H7AA(0.5) H7AB(0.5) H7AC(0.5) N1AA(0.5) C8AA(0.5)
 O2AA(0.5) C0BA(0.5) H0BA(0.5) H0BB(0.5) H0BC(0.5) C9AA(0.5) H9AA(0.5)
 H9AB(0.5) H9AC(0.5) C1BA(0.5) H1BA(0.5) H1BB(0.5) H1BC(0.5) O3AA(0.5)
 N2AA(0.5) C2BA(0.5) C3BA(0.5) H3BA(0.5) H3BB(0.5) H3BC(0.5) C4BA(0.5)
 H4BA(0.5) H4BB(0.5) H4BC(0.5) C5BA(0.5) H5BA(0.5) H5BB(0.5) H5BC(0.5) H3(0.5)
7.a Riding coordinates:
 O4(H4)
7.b Secondary CH2 refined with riding coordinates:
 C43(H43A,H43B), C45(H45A,H45B), C50(H50A,H50B), C51(H51A,H51B), C52(H52A,
 H52B), C53(H53A,H53B)
7.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4A), C5(H5), C11(H11), C12(H12), C15(H15), C17(H17),
 C18(H18), C19(H19), C21(H21), C22(H22), C23(H23), C25(H25), C27(H27), C28(H28),
  C30(H30), C32(H32), C33(H33), C34(H34), C35(H35), C36(H36), C39(H39),
 C41(H41), C44(H44), C54(H54), C55(H55), C56(H56), C57(H57), C58(H58), C59(H59),
  C60(H60)
7.d Fitted hexagon refined as free rotating group:
 N2(C1,C2,C3,C4,C5), C30(C31,C32,C33,N1,C34)
7.e Idealised Me refined as rotating group:
 C3AA(H3AA,H3AB,H3AC), C1AA(H1AA,H1AB,H1AC), C2AA(H2AA,H2AB,H2AC), C5AA(H5AA,
 H5AB,H5AC), C6AA(H6AA,H6AB,H6AC), C7AA(H7AA,H7AB,H7AC), C0BA(H0BA,H0BB,H0BC),
 C9AA(H9AA,H9AB,H9AC), C1BA(H1BA,H1BB,H1BC), C3BA(H3BA,H3BB,H3BC), C4BA(H4BA,
 H4BB,H4BC), C5BA(H5BA,H5BB,H5BC)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              69268
_shelx_hkl_checksum              36094
_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 2.444
_oxdiff_exptl_absorpt_empirical_full_min 0.667