Phenalenyl-ruthenium synergism for effectual catalytic transformations of primary amines to amides.
Bandopadhyay, Nilaj; Paramanik, Krishnendu; Sarkar, Gayetri; Roy, Suvojit; Panda, Subhra Jyoti; Purohit, Chandra Shekhar; Biswas, Bhaskar; Das, Hari Sankar; Dalton transactions (Cambridge, England : 2003) 53 (2024) 13795–13804; doi:10.1039/d4dt01760a

data_7716727
_publ_section_title
;
 Phenalenyl-ruthenium synergism for effectual catalytic transformations of
 primary amines to amides.
;
_journal_issue                   33
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              13795
_journal_page_last               13804
_journal_paper_doi               10.1039/d4dt01760a
_journal_volume                  53
_journal_year                    2024
_chemical_formula_moiety         'C23 H21 Cl O2 Ru'
_chemical_formula_sum            'C23 H21 Cl O2 Ru'
_chemical_formula_weight         465.92
_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   geom
_audit_creation_date             2024-01-12
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2024-02-07 deposited with the CCDC.	2024-07-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.4160(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.73060(10)
_cell_length_b                   14.70960(10)
_cell_length_c                   12.85330(10)
_cell_measurement_reflns_used    28529
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      66.5500
_cell_measurement_theta_min      2.9920
_cell_volume                     1955.81(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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    -24.00  35.00   0.50    0.50    --  -40.33  12.00 -30.00  118
  2  \w    -24.00  35.00   0.50    0.50    --  -40.33  12.00 -90.00  118
  3  \w    -31.00  30.00   0.50    0.50    --  -40.33  25.00 -60.00  122
  4  \w    -24.00  35.00   0.50    0.50    --  -40.33  12.00  60.00  118
  5  \w    -24.00  35.00   0.50    0.50    --  -40.33  12.00 120.00  118
  6  \w    -30.00  31.00   0.50    0.50    --   40.33 -25.00  90.00  122
  7  \w     18.00  79.00   0.50    0.50    --   40.33-104.00  90.00  122
  8  \w     40.00  98.00   0.50    0.50    --   40.33-136.00  93.00  116
  9  \w     40.00 120.00   0.50    1.00    --   96.67-136.00  93.00  160
 10  \w     44.00 127.00   0.50    1.00    --   96.67-145.00  60.00  166
 11  \w     39.00  96.00   0.50    0.50    --   40.33-134.00 -87.00  114
 12  \w     39.00 119.00   0.50    1.00    --   96.67-134.00 -87.00  160
 13  \w     29.00  68.00   0.50    1.00    --   96.67 -59.00 -60.00   78
 14  \w     30.00  57.00   0.50    1.00    --   96.67 -50.00 -90.00   54
 15  \w     30.00  57.00   0.50    1.00    --   96.67 -50.00 -60.00   54
 16  \w     29.00  83.00   0.50    1.00    --   96.67 -68.00 -30.00  108
 17  \w     30.00 109.00   0.50    1.00    --   96.67-117.00 -90.00  158
 18  \w     30.00 109.00   0.50    1.00    --   96.67-117.00-180.00  158
 19  \w     30.00  57.00   0.50    1.00    --   96.67 -50.00 -30.00   54
 20  \w     30.00  57.00   0.50    1.00    --   96.67 -50.00   0.00   54
 21  \w     29.00  83.00   0.50    1.00    --   96.67 -68.00   0.00  108
 22  \w     30.00 109.00   0.50    1.00    --   96.67-117.00  90.00  158
 23  \w     30.00  57.00   0.50    1.00    --   96.67 -50.00 150.00   54
 24  \w     29.00  68.00   0.50    1.00    --   96.67 -59.00 150.00   78
 25  \w     28.00 105.00   0.50    1.00    --   96.67 -77.00 120.00  154
 26  \w     37.00 174.00   0.50    1.00    --   96.67   8.00 150.00  274
 27  \w    105.00 170.00   0.50    1.00    --   96.67  96.00  60.00  130
 28  \w    105.00 170.00   0.50    1.00    --   96.67  96.00 -30.00  130
 29  \w    105.00 170.00   0.50    1.00    --   96.67  96.00  30.00  130
 30  \w     99.00 164.00   0.50    1.00    --   96.67 117.00 -90.00  130
 31  \w     99.00 164.00   0.50    1.00    --   96.67 117.00-150.00  130
 32  \w     89.00 164.00   0.50    1.00    --   96.67 134.00 -20.00  150
 33  \w     80.00 163.00   0.50    1.00    --   96.67  42.00-180.00  166
 34  \w     80.00 163.00   0.50    1.00    --   96.67  42.00   0.00  166
 35  \w     87.00 164.00   0.50    1.00    --   96.67 136.00 157.00  154
 36  \w     78.00 163.00   0.50    1.00    --   96.67  50.00 120.00  170
 37  \w     81.00 164.00   0.50    1.00    --   96.67 145.00  60.00  166
 38  \w     81.00 164.00   0.50    1.00    --   96.67 145.00  30.00  166
 39  \w     75.00 164.00   0.50    1.00    --   96.67  59.00  30.00  178
 40  \w     28.00 105.00   0.50    1.00    --   96.67 -77.00-120.00  154
 41  \w     22.00 106.00   0.50    1.00    --   96.67 -96.00 -30.00  168
 42  \w     29.00  83.00   0.50    1.00    --   96.67 -68.00 120.00  108
 43  \w     28.00 105.00   0.50    1.00    --   96.67 -77.00  90.00  154
 44  \w     22.00 106.00   0.50    1.00    --   96.67 -96.00  90.00  168
 45  \w     25.00 107.00   0.50    0.50    --   40.33  38.00 -90.00  164
 46  \w      8.00  35.00   0.50    0.50    --   40.33  93.00  25.75   54
 47  \w      7.00  35.00   0.50    0.50    --   40.33  94.00  62.37   56
 48  \w      9.00  42.00   0.50    0.50    --   40.33  91.00  84.63   66
 49  \w     12.00  43.00   0.50    0.50    --   40.33  81.00 175.92   62
 50  \w    -35.00  24.00   0.50    0.50    --   40.33 -12.00 150.00  118
 51  \w    -57.00  26.00   0.50    0.50    --  -40.33  50.00   0.00  166
 52  \w    -47.00 -15.00   0.50    1.00    --  -82.50  42.00  30.00   64
 53  \w    -47.00 -15.00   0.50    1.00    --  -82.50  42.00 120.00   64
 54  \w    -47.00 -15.00   0.50    1.00    --  -82.50  42.00 150.00   64
 55  \w    -95.00 -18.00   0.50    0.50    --  -40.33 136.00 157.00  154
 56  \w    -35.00  24.00   0.50    0.50    --   40.33 -12.00 -60.00  118
 57  \w     14.00 109.00   0.50    0.50    --   40.33  77.00 -90.00  190
 58  \w     10.00  43.00   0.50    0.50    --   40.33  88.00 -39.62   66
 59  \w     11.00  43.00   0.50    0.50    --   40.33  86.00-168.22   64
 60  \w    -47.00 -15.00   0.50    1.00    --  -82.50  42.00-180.00   64
 61  \w    -47.00 -15.00   0.50    1.00    --  -82.50  42.00-120.00   64
 62  \w    -57.00 -16.00   0.50    1.00    --  -82.50  50.00-150.00   82
 63  \w    -57.00 -16.00   0.50    1.00    --  -82.50  50.00 -30.00   82
 64  \w    -94.00 -17.00   0.50    0.50    --  -40.33 134.00 -20.00  154
 65  \w    -93.00 -17.00   0.50    1.00    --  -82.50 134.00 -20.00  152
 66  \w   -110.00 -26.00   0.50    0.50    --  -40.33 -25.00  60.00  168
 67  \w   -107.00 -21.00   0.50    0.50    --  -40.33 -50.00 -60.00  172
 68  \w   -107.00 -21.00   0.50    0.50    --  -40.33 -50.00 -30.00  172
 69  \w   -107.00 -21.00   0.50    0.50    --  -40.33 -50.00   0.00  172
 70  \w   -108.00 -17.00   0.50    0.50    --  -40.33 -64.00-180.00  182
 71  \w   -108.00 -17.00   0.50    0.50    --  -40.33 -64.00 -90.00  182
 72  \w   -109.00 -13.00   0.50    0.50    --  -40.33 -77.00  90.00  192
 73  \w   -149.00 -67.00   0.50    1.00    --  -82.50-134.00 -87.00  164
 74  \w   -150.00 -65.00   0.50    1.00    --  -82.50-136.00  93.00  170
 75  \w   -150.00 -57.00   0.50    1.00    --  -82.50 -70.00 160.90  186
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix3000'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.1356
_diffrn_reflns_av_unetI/netI     0.0399
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            31991
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        66.598
_diffrn_reflns_theta_max         66.598
_diffrn_reflns_theta_min         4.666
_exptl_absorpt_coefficient_mu    7.860
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.51874
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear reddish black'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   reddish
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.582
_exptl_crystal_description       block
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         3.140
_refine_diff_density_min         -2.758
_refine_diff_density_rms         0.225
_refine_ls_extinction_coef       0.0087(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         3457
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.098
_refine_ls_R_factor_all          0.0687
_refine_ls_R_factor_gt           0.0685
_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^)+(0.1367P)^2^+1.9660P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1722
_refine_ls_wR_factor_ref         0.1727
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3433
_reflns_number_total             3457
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4dt01760a2.cif
_cod_data_source_block           nb8_rt_1
_cod_depositor_comments
'Adding full bibliography for 7716726--7716728.cif.'
_cod_database_code               7716727
_shelx_shelxl_version_number     2019/2
_shelx_estimated_absorpt_t_max   0.507
_shelx_estimated_absorpt_t_min   0.302
_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
2.a Ternary CH refined with riding coordinates:
 C16(H16)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C7(H7), C8(H8), C11(H11), C12(H12),
 C14(H14), C15(H15)
2.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C19(H19A,H19B,H19C)
;
_shelx_res_checksum              91656
_shelx_hkl_checksum              67659
_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
;