Formic acid dehydrogenation catalysed by a novel amino-di(N-heterocyclic carbene) based Ru-CNC pincer complex.
Aufricht, Patricia; Nori, Valeria; Rabell, Brenda; Piccirilli, Luca; Koranchalil, Sakhitha; W Larsen, René; Nielsen, Mathias T.; Nielsen, Martin; Chemical communications (Cambridge, England) 61 (2025) 3986–3989; doi:10.1039/d4cc05164e

data_7134174
_publ_section_title
;
 Formic acid dehydrogenation catalysed by a novel amino-di(N-heterocyclic
 carbene) based Ru-CNC pincer complex.
;
_journal_issue                   20
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              3986
_journal_page_last               3989
_journal_paper_doi               10.1039/d4cc05164e
_journal_volume                  61
_journal_year                    2025
_chemical_formula_moiety         'C17 H27 Cl2 N5 O Ru'
_chemical_formula_sum            'C17 H27 Cl2 N5 O Ru'
_chemical_formula_weight         489.40
_chemical_properties_physical    'Air-sensitive,Air sensitive over several days'
_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             2024-09-29
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-09-30 deposited with the CCDC.	2025-01-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.669(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.1376(2)
_cell_length_b                   15.2198(2)
_cell_length_c                   13.6429(2)
_cell_measurement_reflns_used    22601
_cell_measurement_temperature    119.99(18)
_cell_measurement_theta_max      70.1080
_cell_measurement_theta_min      4.3200
_cell_volume                     2100.68(6)
_computing_cell_refinement       'CrysAlisPro 1.171.41.115a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.115a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.115a (Rigaku OD, 2021)'
_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      119.99(18)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3073
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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    -71.00  27.00   1.00    5.62    --  -40.81  73.00  11.00   98
  2  \w     23.00  60.00   1.00    5.62    --   40.81 -73.00-116.00   37
  3  \w     45.00 103.00   1.00   22.47    --  112.00 -73.00-116.00   58
  4  \w    133.00 178.00   1.00   22.47    --  112.00  73.00  11.00   45
  5  \w    -86.00  -7.00   1.00    5.62    --  -40.81 125.00  90.00   79
  6  \w   -114.00 -34.00   1.00    5.62    --  -40.81 -38.00-120.00   80
  7  \w   -111.00 -19.00   1.00    5.62    --  -40.81 -38.00 150.00   92
  8  \w    -26.00  29.00   1.00    5.62    --   40.81 -38.00 -90.00   55
  9  \w     54.00  80.00   1.00    5.62    --   40.81 -99.00  90.00   26
 10  \w     11.00  37.00   1.00    5.62    --   40.81 -99.00  90.00   26
 11  \w     79.00 131.00   1.00   22.47    --  112.00 178.00 150.00   52
 12  \w    104.00 165.00   1.00   22.47    --  112.00  77.00 150.00   61
 13  \w     72.00 100.00   1.00   22.47    --  112.00-111.00-150.00   28
 14  \w     52.00 108.00   1.00   22.47    --  112.00-111.00 120.00   56
 15  \w     35.00  86.00   1.00   22.47    --  112.00 -95.00-120.00   51
 16  \w    135.00 178.00   1.00   22.47    --  112.00  77.00 120.00   43
 17  \w     39.00 109.00   1.00   22.47    --  112.00-111.00 150.00   70
 18  \w     83.00 160.00   1.00   22.47    --  112.00  61.00  30.00   77
 19  \w     62.00  88.00   1.00   22.47    --  112.00 178.00  30.00   26
 20  \w     72.00  99.00   1.00   22.47    --  112.00-111.00   0.00   27
 21  \w     62.00 104.00   1.00   22.47    --  112.00-111.00  60.00   42
 22  \w    107.00 168.00   1.00   22.47    --  112.00 111.00 -30.00   61
 23  \w     52.00 111.00   1.00   22.47    --  112.00 -45.00  90.00   59
 24  \w     92.00 121.00   1.00   22.47    --  112.00 178.00  30.00   29
 25  \w    103.00 178.00   1.00   22.47    --  112.00  77.00-120.00   75
 26  \w     43.00  92.00   1.00   22.47    --  112.00-111.00-180.00   49
 27  \w     83.00 109.00   1.00   22.47    --  112.00-111.00 -60.00   26
 28  \w     57.00 109.00   1.00   22.47    --  112.00-111.00  30.00   52
 29  \w     96.00 123.00   1.00   22.47    --  112.00  45.00 -30.00   27
 30  \w    145.00 171.00   1.00   22.47    --  112.00  45.00 -30.00   26
 31  \w     71.00 109.00   1.00   22.47    --  112.00-111.00-120.00   38
 32  \w    116.00 145.00   1.00   22.47    --  112.00 111.00-150.00   29
 33  \w    102.00 145.00   1.00   22.47    --  112.00 178.00  60.00   43
 34  \w     90.00 177.00   1.00   22.47    --  112.00  45.00 -60.00   87
 35  \w     40.00  84.00   1.00   22.47    --  112.00 -95.00  90.00   44
 36  \w     -9.00  25.00   1.00    5.62    --   40.81 -73.00-116.00   34
 37  \w    -10.00  22.00   1.00    5.62    --  -40.81  38.00-150.00   32
 38  \w   -114.00 -16.00   1.00    5.62    --  -40.81 -38.00  30.00   98
 39  \w    -58.00 -24.00   1.00    5.62    --  -40.81  38.00-150.00   34
 40  \w     20.00  45.00   1.00    5.62    --   40.81  57.00-120.00   25
 41  \w      7.00  32.00   1.00    5.62    --   40.81  85.00-177.97   25
 42  \w     10.00  42.00   1.00    5.62    --   40.81  80.00 140.67   32
 43  \w      6.00  32.00   1.00    5.62    --   40.81  85.00 -54.19   26
 44  \w      8.00  38.00   1.00    5.62    --   40.81  82.00  63.72   30
 45  \w     13.00 111.00   1.00    5.62    --   40.81  57.00   0.00   98
 46  \w     66.00 114.00   1.00    5.62    --   40.81  57.00-120.00   48
 47  \w     10.00  36.00   1.00    5.62    --   40.81  73.00 108.56   26
 48  \w      5.00  31.00   1.00    5.62    --   40.81  87.00  -6.57   26
 49  \w     20.00  63.00   1.00    5.62    --   40.81  57.00-180.00   43
 50  \w      6.00  32.00   1.00    5.62    --   40.81  85.00 -98.53   26
 51  \w     83.00 109.00   1.00   22.47    --  112.00  61.00 -90.00   26
 52  \w     83.00 124.00   1.00   22.47    --  112.00  61.00   0.00   41
 53  \w     81.00 107.00   1.00   22.47    --  112.00  69.00-114.40   26
 54  \w     82.00 109.00   1.00   22.47    --  112.00  68.00  86.25   27
 55  \w    129.00 173.00   1.00   22.47    --  112.00  61.00-180.00   44
 56  \w     83.00 109.00   1.00   22.47    --  112.00  61.00 150.00   26
 57  \w    150.00 176.00   1.00   22.47    --  112.00  61.00  60.00   26
 58  \w     83.00 110.00   1.00   22.47    --  112.00  61.00-180.00   27
 59  \w    139.00 177.00   1.00   22.47    --  112.00  67.00  45.77   38
 60  \w     83.00 119.00   1.00   22.47    --  112.00  63.00  19.06   36
 61  \w     87.00 155.00   1.00   22.47    --  112.00  45.00 150.00   68
 62  \w    130.00 156.00   1.00   22.47    --  112.00  65.00-168.86   26
 63  \w     82.00 108.00   1.00   22.47    --  112.00  67.00  45.77   26
 64  \w     81.00 118.00   1.00   22.47    --  112.00  70.00  99.21   37
 65  \w    140.00 171.00   1.00   22.47    --  112.00  70.00  99.21   31
 66  \w     83.00 125.00   1.00   22.47    --  112.00  61.00-150.00   42
 67  \w     82.00 108.00   1.00   22.47    --  112.00  68.00-127.39   26
 68  \w     82.00 116.00   1.00   22.47    --  112.00  65.00-168.86   34
 69  \w    134.00 178.00   1.00   22.47    --  112.00  71.00 159.24   44
 70  \w     84.00 140.00   1.00   22.47    --  112.00  58.00  88.92   56
 71  \w     82.00 145.00   1.00   22.47    --  112.00  68.00  66.84   63
 72  \w     82.00 108.00   1.00   22.47    --  112.00  64.00 -78.46   26
 73  \w     83.00 109.00   1.00   22.47    --  112.00  61.00 -30.00   26
 74  \w    148.00 174.00   1.00   22.47    --  112.00  58.00  88.92   26
 75  \w     82.00 146.00   1.00   22.47    --  112.00  66.00-144.38   64
 76  \w    118.00 144.00   1.00   22.47    --  112.00  45.00 -30.00   26
 77  \w     83.00 124.00   1.00   22.47    --  112.00  61.00 120.00   41
 78  \w     87.00 112.00   1.00   22.47    --  112.00  45.00 -30.00   25
 79  \w    140.00 170.00   1.00   22.47    --  112.00  60.00  39.37   30
 80  \w     81.00 107.00   1.00   22.47    --  112.00  71.00 -73.26   26
 81  \w    143.00 178.00   1.00   22.47    --  112.00  71.00 -73.26   35
 82  \w     83.00 110.00   1.00   22.47    --  112.00  60.00  39.37   27
 83  \w    130.00 156.00   1.00   22.47    --  112.00  61.00 -90.00   26
 84  \w     81.00 107.00   1.00   22.47    --  112.00  71.00 159.24   26
 85  \w     84.00 125.00   1.00   22.47    --  112.00  61.00  60.00   41
 86  \w     84.00 131.00   1.00   22.47    --  112.00  57.00 -10.61   47
;
_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      -0.0962351000
_diffrn_orient_matrix_UB_12      0.0497815000
_diffrn_orient_matrix_UB_13      -0.0722001000
_diffrn_orient_matrix_UB_21      0.0295911000
_diffrn_orient_matrix_UB_22      -0.0654514000
_diffrn_orient_matrix_UB_23      -0.0818899000
_diffrn_orient_matrix_UB_31      -0.1142332000
_diffrn_orient_matrix_UB_32      -0.0589463000
_diffrn_orient_matrix_UB_33      0.0299481000
_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  0.0769
_diffrn_reflns_av_unetI/netI     0.0296
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            41312
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.049
_diffrn_reflns_theta_min         4.357
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    8.511
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56526
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.115a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.547
_exptl_crystal_description       block
_exptl_crystal_F_000             1000
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: THF and Et2O'
_exptl_crystal_size_max          0.029
_exptl_crystal_size_mid          0.019
_exptl_crystal_size_min          0.017
_refine_diff_density_max         1.669
_refine_diff_density_min         -0.953
_refine_diff_density_rms         0.100
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         3994
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0379
_refine_ls_R_factor_gt           0.0340
_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^)+(0.0601P)^2^+0.7445P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0861
_refine_ls_wR_factor_ref         0.0882
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3596
_reflns_number_total             3994
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc05164e2.cif
_cod_data_source_block           exp_199-pa_11
_cod_depositor_comments          'Adding full bibliography for 7134174.cif.'
_cod_database_code               7134174
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C17 H27 Cl2 N5 O1 Ru1'
_chemical_oxdiff_usercomment     PA_11
_shelx_estimated_absorpt_t_max   0.869
_shelx_estimated_absorpt_t_min   0.790
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 N00C(H00C), C00D(H00D), C00G(H00G)
2.b Secondary CH2 refined with riding coordinates:
 C00F(H00a,H00f), C00H(H00h,H00i), C00I(H00j,H00k), C00J(H00l,H00m)
2.c Aromatic/amide H refined with riding coordinates:
 C00B(H00B), C00E(H00E), C00K(H00n), C00M(H00o)
2.d Idealised Me refined as rotating group:
 C00N(H00p,H00q,H00r), C00O(H00s,H00t,H00u), C00P(H00v,H00w,H00x), C00Q(H00y,H,
 Ha)
;
_shelx_res_checksum              16513
_shelx_hkl_checksum              19092
_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 2.621
_oxdiff_exptl_absorpt_empirical_full_min 0.294