Ru<sup>II</sup>-phosphine catalysed direct synthesis of benzimidazoles <i>via</i> acceptorless dehydrogenative coupling of alcohols with aromatic diamines.
Pandey, Ankit; Balakrishna, Maravanji S.; Organic & biomolecular chemistry 23 (2025) 8795–8804; doi:10.1039/d5ob01280e

data_7160717
_publ_section_title
;
 Ru<sup>II</sup>-phosphine catalysed direct synthesis of benzimidazoles
 <i>via</i> acceptorless dehydrogenative coupling of alcohols with
 aromatic diamines.
;
_journal_issue                   38
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              8795
_journal_page_last               8804
_journal_paper_doi               10.1039/d5ob01280e
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C37 H38 Cl N O2 P Ru, Cl'
_chemical_formula_sum            'C37 H38 Cl2 N O2 P Ru'
_chemical_formula_weight         731.66
_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'
_symmetry_Int_Tables_number      14
_atom_sites_solution_primary     iterative
_audit_creation_date             2025-07-18
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_audit_update_record
;
2025-07-24 deposited with the CCDC.	2025-09-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.547(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   21.478(3)
_cell_length_b                   9.9044(15)
_cell_length_c                   18.416(3)
_cell_measurement_reflns_used    9868
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      27.33
_cell_measurement_theta_min      2.24
_cell_volume                     3774.2(10)
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.9998
_diffrn_measured_fraction_theta_max 0.9998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1058
_diffrn_reflns_av_unetI/netI     0.0619
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            79382
_diffrn_reflns_theta_full        25.0000
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.97
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.630
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5326
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1596 before and 0.0778 after correction.
The Ratio of minimum to maximum transmission is 0.7142.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear brownish brown'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   brownish
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.2875
_exptl_crystal_description       needle
_exptl_crystal_F_000             1501.1212
_exptl_crystal_size_max          0.59
_exptl_crystal_size_mid          0.066
_exptl_crystal_size_min          0.064
_refine_diff_density_max         0.6273
_refine_diff_density_min         -0.6194
_refine_diff_density_rms         0.1146
_refine_ls_d_res_high            0.8409
_refine_ls_d_res_low             10.3460
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_goodness_of_fit_ref   1.0722
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    67
_refine_ls_number_parameters     402
_refine_ls_number_reflns         6648
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0722
_refine_ls_R_factor_all          0.0560
_refine_ls_R_factor_gt           0.0391
_refine_ls_shift/su_max          0.0002
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0199P)^2^+7.7674P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0798
_refine_ls_wR_factor_ref         0.0884
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              24
_reflns_limit_h_min              -25
_reflns_limit_k_max              11
_reflns_limit_k_min              0
_reflns_limit_l_max              21
_reflns_limit_l_min              0
_reflns_number_gt                5282
_reflns_number_total             6648
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d5ob01280e2.cif
_cod_data_source_block           Compound_2
_cod_depositor_comments          'Adding full bibliography for 7160717.cif.'
_cod_original_cell_volume        3774.3(10)
_cod_database_code               7160717
_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:
 C34(H34)
2.b Secondary CH2 refined with riding coordinates:
 C26(H26a,H26b)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C29(H29), C5(H5), C21(H21), C19(H19), C31(H31), C3(H3),
 C25(H25), C22(H22), C28(H28), C24(H24), C4(H4), C15(H15), C23(H23), C13(H13),
 C18(H18), C10(H10), C16(H16), C32(H32), C17(H17), C11(H11), C12(H12)
2.d Idealised Me refined as rotating group:
 C37(H37a,H37b,H37c), C27(H27a,H27b,H27c), C35(H35a,H35b,H35c), C36(H36a,H36b,
 H36c)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_submission_special_instructions 'No special instructions were received'