Boron appended Ru-NHC catalyzed selective deoxygenative hydrogenation of tertiary amides and desulfurization of thioamides
Sharma, Raju; Kenguva, Gowtham; Dandela, Rambabu; Daw, Prosenjit; Chemical Communications 61 (2025) 9460–9463; doi:10.1039/D5CC00399G

data_7134547
_publ_section_title
;
 Boron appended Ru-NHC catalyzed selective deoxygenative hydrogenation of
 tertiary amides and desulfurization of thioamides
;
_journal_issue                   52
_journal_name_full               'Chemical Communications'
_journal_page_first              9460
_journal_page_last               9463
_journal_paper_doi               10.1039/D5CC00399G
_journal_volume                  61
_journal_year                    2025
_chemical_formula_moiety         'C32 H47 B Cl N4 O2 Ru, 1(F6 P)'
_chemical_formula_sum            'C32 H47 B Cl F6 N4 O2 P Ru'
_chemical_formula_weight         812.03
_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             2024-02-15
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2024-04-20 deposited with the CCDC.	2025-05-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.422(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.2664(10)
_cell_length_b                   13.8510(7)
_cell_length_c                   14.4079(8)
_cell_measurement_reflns_used    9361
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      26.41
_cell_measurement_theta_min      2.67
_cell_volume                     3645.2(3)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      273.15
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0443
_diffrn_reflns_av_unetI/netI     0.0228
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            66172
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.449
_diffrn_reflns_theta_min         3.015
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.613
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6882
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1246 before and 0.0612 after correction.
The Ratio of minimum to maximum transmission is 0.9233.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light brown'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.480
_exptl_crystal_description       block
_exptl_crystal_F_000             1672
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         1.769
_refine_diff_density_min         -0.931
_refine_diff_density_rms         0.085
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     504
_refine_ls_number_reflns         7465
_refine_ls_number_restraints     141
_refine_ls_restrained_S_all      1.133
_refine_ls_R_factor_all          0.0486
_refine_ls_R_factor_gt           0.0424
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0417P)^2^+9.2588P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1025
_refine_ls_wR_factor_ref         0.1072
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6709
_reflns_number_total             7465
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc00399g2.cif
_cod_data_source_block           10jane_0ma
_cod_depositor_comments
'Adding full bibliography for 7134546--7134547.cif.'
_cod_database_code               7134547
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_max   0.930
_shelx_estimated_absorpt_t_min   0.867
_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
2. Restrained distances
 P1-F1 \\sim P1A-F2A
 with sigma of 0.02
 P1-F6 \\sim P1A-F3A
 with sigma of 0.02
 P1-F4 \\sim P1A-F4A
 with sigma of 0.02
 P1-F2 \\sim P1A-F5A
 with sigma of 0.02
 P1-F3 \\sim P1A-F1A
 with sigma of 0.02
 F1-F6 \\sim F2A-F3A
 with sigma of 0.04
 F1-F4 \\sim F2A-F4A
 with sigma of 0.04
 F1-F2 \\sim F2A-F5A
 with sigma of 0.04
 F1-F3 \\sim F2A-F1A
 with sigma of 0.04
 F6-F4 \\sim F3A-F4A
 with sigma of 0.04
 F6-F2 \\sim F3A-F5A
 with sigma of 0.04
 F6-F3 \\sim F3A-F1A
 with sigma of 0.04
 F4-F2 \\sim F4A-F5A
 with sigma of 0.04
 F4-F3 \\sim F4A-F1A
 with sigma of 0.04
 F2-F3 \\sim F5A-F1A
 with sigma of 0.04
3. Rigid body (RIGU) restrains
 P1, P1A, F1, F1A, F2, F2A, F3, F3A, F4, F4A, F5, F5A, F6, F6A
 with sigma for 1-2 distances of 0.0005 and sigma for 1-3 distances of 0.0005
4. Others
 Sof(P1A)=Sof(F1A)=Sof(F2A)=Sof(F3A)=Sof(F4A)=Sof(F5A)=Sof(F6A)=1-FVAR(1)
 Sof(P1)=Sof(F1)=Sof(F2)=Sof(F3)=Sof(F4)=Sof(F5)=Sof(F6)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C24(H24)
5.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C14(H14A,
 H14B), C15(H15A,H15B), C22(H22A,H22B)
5.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C11(H11), C12(H12), C27(H27), C28(H28), C30(H30),
 C31(H31)
5.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C21(H21A,H21B,
 H21C), C23(H23A,H23B,H23C), C25(H25A,H25B,H25C), C32(H32A,H32B,H32C)
;
_shelx_res_checksum              20477
_shelx_hkl_checksum              94933
_olex2_submission_special_instructions 'No special instructions were received'