Copper(i) anchored on a covalent triazine framework/ionic liquid as a recyclable catalytic system for cyclization of propargylic amines with CO2 under ambient conditions
Guan, Yu; Wang, Bin; Ying, Yan-Ling; Li, Ping; Zhang, Zhan-Hui; Green Chemistry 27 (2025) 9165–9177; doi:10.1039/D5GC02137E

data_7250604
_publ_section_title
;
 Copper(i) anchored on a covalent triazine framework/ionic liquid as a
 recyclable catalytic system for cyclization of propargylic amines with
 CO2 under ambient conditions
;
_journal_issue                   30
_journal_name_full               'Green Chemistry'
_journal_page_first              9165
_journal_page_last               9177
_journal_paper_doi               10.1039/D5GC02137E
_journal_volume                  27
_journal_year                    2025
_chemical_formula_moiety         'C13 H13 N O4'
_chemical_formula_sum            'C13 H13 N O4'
_chemical_formula_weight         247.24
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2025-04-09
_audit_creation_method
;
Olex2 1.5-ac5-023
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_audit_update_record
;
2025-04-10 deposited with the CCDC.	2025-06-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.314(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   23.8084(4)
_cell_length_b                   4.61710(10)
_cell_length_c                   11.0799(2)
_cell_measurement_reflns_used    4853
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      75.9720
_cell_measurement_theta_min      3.7450
_cell_volume                     1216.97(4)
_computing_cell_refinement       'CrysAlisPro 1.171.43.142a (Rigaku OD, 2024)'
_computing_data_collection       'CrysAlisPro 1.171.43.142a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.142a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5-ac5-023 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-023 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.957
_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    -65.00 -20.00   0.50    1.18    --  -91.75  57.00-120.00   90
  2  \w    -47.00 -22.00   0.50    1.18    --  -91.75  57.00 -90.00   50
  3  \w    -54.00 -21.00   0.50    1.18    --  -91.75  57.00 -60.00   66
  4  \w    -64.00 -20.00   0.50    1.18    --  -91.75  57.00 150.00   88
  5  \w    -47.00 -22.00   0.50    1.18    --  -91.75  42.00  57.00   50
  6  \w   -145.00-119.00   0.50    1.18    --  -91.75 -42.00 -94.00   52
  7  \w   -119.00 -39.00   0.50    0.30    --  -47.34 -42.00 -94.00  160
  8  \w      1.00  28.00   0.50    0.30    --  -47.34  19.00-180.00   54
  9  \w    -46.00  11.00   0.50    0.30    --  -47.34  42.00  57.00  114
 10  \w     47.00 103.00   0.50    1.18    --  108.72 -99.00-180.00  112
 11  \w     48.00  74.00   0.50    1.18    --  108.72 -99.00 -30.00   52
 12  \w     37.00 105.00   0.50    1.18    --  108.72 -77.00 -90.00  136
 13  \w     40.00  65.00   0.50    1.18    --  108.72 -57.00-150.00   50
 14  \w     36.00  66.00   0.50    1.18    --  108.72 -57.00-180.00   60
 15  \w     38.00  64.00   0.50    1.18    --  108.72 -57.00 -90.00   52
 16  \w     37.00  62.00   0.50    1.18    --  108.72 -57.00 -30.00   50
 17  \w     36.00  61.00   0.50    1.18    --  108.72 -57.00   0.00   50
 18  \w    -26.00  25.00   0.50    0.30    --   47.34 -19.00 150.00  102
 19  \w     40.00  65.00   0.50    1.18    --  108.72 -57.00 150.00   50
 20  \w     38.00  64.00   0.50    1.18    --  108.72 -57.00  90.00   52
 21  \w      4.00  38.00   0.50    0.30    --   47.34 -42.00 -94.00   68
 22  \w     95.00 173.00   0.50    1.18    --  108.72  38.00   0.00  156
 23  \w    104.00 168.00   0.50    1.18    --  108.72  42.00  57.00  128
 24  \w     53.00  88.00   0.50    0.30    --   47.34  42.00  57.00   70
 25  \w     99.00 135.00   0.50    1.18    --  108.72  57.00 150.00   72
 26  \w    153.00 178.00   0.50    1.18    --  108.72  57.00 150.00   50
;
_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      0.0535819000
_diffrn_orient_matrix_UB_12      -0.1691960000
_diffrn_orient_matrix_UB_13      0.0383054000
_diffrn_orient_matrix_UB_21      0.0238259000
_diffrn_orient_matrix_UB_22      0.0547127000
_diffrn_orient_matrix_UB_23      -0.1251907000
_diffrn_orient_matrix_UB_31      0.0274798000
_diffrn_orient_matrix_UB_32      0.2823706000
_diffrn_orient_matrix_UB_33      0.0471183000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0246
_diffrn_reflns_av_unetI/netI     0.0278
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7899
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.762
_diffrn_reflns_theta_min         3.716
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.843
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61723
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.142a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.171
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2447
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0472
_refine_ls_R_factor_gt           0.0429
_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^)+(0.0688P)^2^+0.1543P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1200
_refine_ls_wR_factor_ref         0.1249
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2114
_reflns_number_total             2447
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5gc02137e2.cif
_cod_data_source_block           20250409-gy-1_auto
_cod_depositor_comments          'Adding full bibliography for 7250604.cif.'
_cod_database_code               7250604
_shelx_shelxl_version_number     2018/1
_chemical_oxdiff_formula         'C H O N'
_shelx_estimated_absorpt_t_max   0.936
_shelx_estimated_absorpt_t_min   0.786
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00B(H00B,H00C), C00F(H00E,H00F), C00G(H00G,H00H), C00H(H00I,H00J)
2.b Aromatic/amide H refined with riding coordinates:
 C009(H009), C00A(H00A), C00C(H00D)
2.c X=CH2 refined with riding coordinates:
 C00I(H00K,H00L)
;
_shelx_res_checksum              23470
_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 1.711
_oxdiff_exptl_absorpt_empirical_full_min 0.461