A recyclable rhodium catalyst anchored onto a bipyridine covalent triazine framework for transfer hydrogenation of N-heteroarenes in water
Everaert, Jonas; Leus, Karen; Rijckaert, Hannes; Debruyne, Maarten; Van Hecke, Kristof; Morent, Rino; De Geyter, Nathalie; Van Speybroeck, Veronique; Van Der Voort, Pascal; Stevens, Christian V.; Green Chemistry 25 (2023) 3267–3277; doi:10.1039/D3GC00167A

data_7246554
_publ_section_title
;
 A recyclable rhodium catalyst anchored onto a bipyridine covalent
 triazine framework for transfer hydrogenation of N-heteroarenes in water
;
_journal_issue                   8
_journal_name_full               'Green Chemistry'
_journal_page_first              3267
_journal_page_last               3277
_journal_paper_doi               10.1039/D3GC00167A
_journal_volume                  25
_journal_year                    2023
_chemical_formula_moiety         'C20 H18 N2'
_chemical_formula_sum            'C20 H18 N2'
_chemical_formula_weight         286.36
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2022-10-07
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2022-12-12 deposited with the CCDC.	2023-03-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.0457(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.54957(13)
_cell_length_b                   5.45668(4)
_cell_length_c                   21.5051(3)
_cell_measurement_reflns_used    21005
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      73.8430
_cell_measurement_theta_min      3.5330
_cell_volume                     1450.07(3)
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_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_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4839
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_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   -115.00 -14.00   1.00    1.00    --  -41.68 -57.00  90.00  101
  2  \w    -87.00  -6.00   1.00    1.00    --  -41.68 125.00 -60.00   81
  3  \w   -115.00 -14.00   1.00    1.00    --  -41.68 -57.00-180.00  101
  4  \w      6.00  83.00   1.00    1.00    --   41.68 -99.00-120.00   77
  5  \w    -21.00  74.00   1.00    1.00    --   41.68 -77.00 -60.00   95
  6  \w     23.00 107.00   1.00    2.00    --  106.01 -94.00-120.00   84
  7  \w     23.00 107.00   1.00    2.00    --  106.01 -94.00 -30.00   84
  8  \w     23.00 107.00   1.00    2.00    --  106.01 -94.00  30.00   84
  9  \w     34.00 135.00   1.00    2.00    --  106.01 -61.00   0.00  101
 10  \w    103.00 178.00   1.00    2.00    --  106.01  77.00   0.00   75
 11  \w     23.00 107.00   1.00    2.00    --  106.01 -94.00-180.00   84
 12  \w     34.00 135.00   1.00    2.00    --  106.01 -61.00-180.00  101
 13  \w     33.00 112.00   1.00    2.00    --  106.01-125.00-180.00   79
 14  \w     78.00 178.00   1.00    2.00    --  106.01  30.00 -30.00  100
 15  \w     30.00 134.00   1.00    2.00    --  106.01 -30.00 150.00  104
 16  \w     24.00 159.00   1.00    2.00    --  106.01 -15.00 -60.00  135
 17  \w    -87.00  -6.00   1.00    1.00    --  -41.68 125.00  30.00   81
 18  \w   -115.00 -14.00   1.00    1.00    --  -41.68 -57.00  30.00  101
 19  \w   -115.00 -14.00   1.00    1.00    --  -41.68 -57.00 -30.00  101
 20  \w   -115.00 -59.00   1.00    1.00    --  -41.68-152.00  29.00   56
 21  \w   -115.00 -14.00   1.00    1.00    --  -41.68 -57.00 -90.00  101
 22  \w     77.00 178.00   1.00    2.00    --  106.01  61.00-180.00  101
 23  \w     77.00 178.00   1.00    2.00    --  106.01  61.00  60.00  101
 24  \w     78.00 178.00   1.00    2.00    --  106.01  30.00 120.00  100
 25  \w     80.00 178.00   1.00    2.00    --  106.01  45.00 150.00   98
 26  \w     77.00 178.00   1.00    2.00    --  106.01  61.00   0.00  101
 27  \w     77.00 178.00   1.00    2.00    --  106.01  61.00-120.00  101
 28  \w     77.00 178.00   1.00    2.00    --  106.01  61.00 -90.00  101
 29  \w     77.00 178.00   1.00    2.00    --  106.01  61.00-150.00  101
 30  \w     77.00 178.00   1.00    2.00    --  106.01  61.00 -30.00  101
 31  \w     77.00 178.00   1.00    2.00    --  106.01  61.00  30.00  101
 32  \w   -115.00 -14.00   1.00    1.00    --  -41.68 -57.00-150.00  101
 33  \w     14.00 115.00   1.00    1.00    --   41.68  57.00-120.00  101
 34  \w     17.00 116.00   1.00    1.00    --   41.68  40.00  48.00   99
 35  \w     17.00 116.00   1.00    1.00    --   41.68  38.00-180.00   99
 36  \w     17.00 116.00   1.00    1.00    --   41.68  38.00 150.00   99
 37  \w     77.00 178.00   1.00    2.00    --  106.01  61.00 150.00  101
 38  \w     80.00 178.00   1.00    2.00    --  106.01  45.00  60.00   98
 39  \w     80.00 178.00   1.00    2.00    --  106.01  45.00 120.00   98
 40  \w     80.00 178.00   1.00    2.00    --  106.01  45.00  30.00   98
 41  \w     77.00 178.00   1.00    2.00    --  106.01  61.00  90.00  101
 42  \w     77.00 178.00   1.00    2.00    --  106.01  61.00 120.00  101
 43  \w     80.00 178.00   1.00    2.00    --  106.01  45.00-180.00   98
 44  \w     80.00 178.00   1.00    2.00    --  106.01  45.00 -90.00   98
 45  \w     80.00 178.00   1.00    2.00    --  106.01  45.00-150.00   98
 46  \w     77.00 178.00   1.00    2.00    --  106.01  61.00 -60.00  101
 47  \w      1.00  52.00   1.00    1.00    --   41.68  19.00 -90.00   51
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0692146000
_diffrn_orient_matrix_UB_12      0.1764478000
_diffrn_orient_matrix_UB_13      -0.0322680000
_diffrn_orient_matrix_UB_21      -0.0669285000
_diffrn_orient_matrix_UB_22      0.2183392000
_diffrn_orient_matrix_UB_23      0.0173680000
_diffrn_orient_matrix_UB_31      0.0791813000
_diffrn_orient_matrix_UB_32      0.0303453000
_diffrn_orient_matrix_UB_33      0.0628439000
_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  0.0278
_diffrn_reflns_av_unetI/netI     0.0107
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            38566
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.787
_diffrn_reflns_theta_min         3.814
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.595
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.661
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_description       block
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.237
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     205
_refine_ls_number_reflns         2917
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0378
_refine_ls_R_factor_gt           0.0351
_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^)+(0.0535P)^2^+0.4333P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0938
_refine_ls_wR_factor_ref         0.0962
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2686
_reflns_number_total             2917
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3gc00167a2.cif
_cod_data_source_block           cs046
_cod_depositor_comments          'Adding full bibliography for 7246554.cif.'
_cod_database_code               7246554
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C20 H18 N2'
_shelx_estimated_absorpt_t_max   0.906
_shelx_estimated_absorpt_t_min   0.866
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1A), C8(H8)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C10(H10), C11(H11), C12(H12), C13(H13),
 C14(H14), C16(H16), C17(H17), C18(H18), C19(H19), C20(H20)
;
_shelx_res_checksum              66757
_olex2_exptl_crystal_mounting_method 'mounted on a LithoLoop'
_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
- B-factor correction
;
_oxdiff_exptl_absorpt_empirical_full_max 2.315
_oxdiff_exptl_absorpt_empirical_full_min 0.754