Catalytic transfer hydrogenation of azobenzene by low-valent nickel complexes: a route to 1,2-disubstituted benzimidazoles and 2,4,5-trisubstituted imidazolines.
Zurita, Daniel A.; Flores-Alamo, Marcos; García, Juventino J; Dalton transactions (Cambridge, England : 2003) 45 (2016) 10389–10401; doi:10.1039/c6dt01674j

data_7040204
_publ_section_title
;
 Catalytic transfer hydrogenation of azobenzene by low-valent nickel
 complexes: a route to 1,2-disubstituted benzimidazoles and
 2,4,5-trisubstituted imidazolines.
;
_journal_issue                   25
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              10389
_journal_page_last               10401
_journal_paper_doi               10.1039/c6dt01674j
_journal_volume                  45
_journal_year                    2016
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C26 H40 F2 N2 Ni P2'
_chemical_formula_sum            'C26 H40 F2 N2 Ni P2'
_chemical_formula_weight         539.25
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           43
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      43
_symmetry_space_group_name_Hall  'F 2 -2d'
_symmetry_space_group_name_H-M   'F d d 2'
_atom_sites_solution_hydrogens   geom
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_creation_date             2016-04-13T19:49:30-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2016-04-19 deposited with the CCDC.
2016-05-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   38.069(2)
_cell_length_b                   17.3973(6)
_cell_length_c                   8.3793(3)
_cell_measurement_reflns_used    4235
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      28.553
_cell_measurement_theta_min      4.529
_cell_volume                     5549.6(4)
_computing_cell_refinement
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
        (compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
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        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
        (compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
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        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
        (compiled Aug  2 2013,16:46:58)
;
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      130(2)
_diffrn_detector_area_resol_mean 10.4685
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.924
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0020693
_diffrn_orient_matrix_UB_12      0.0397522
_diffrn_orient_matrix_UB_13      0.0166597
_diffrn_orient_matrix_UB_21      0.0000392
_diffrn_orient_matrix_UB_22      -0.0081476
_diffrn_orient_matrix_UB_23      0.0828417
_diffrn_orient_matrix_UB_31      0.0185256
_diffrn_orient_matrix_UB_32      -0.0044002
_diffrn_orient_matrix_UB_33      -0.0020443
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_av_unetI/netI     0.0448
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.924
_diffrn_reflns_limit_h_max       48
_diffrn_reflns_limit_h_min       -49
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            9727
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.853
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.491
_diffrn_reflns_theta_min         3.801
_exptl_absorpt_coefficient_mu    0.844
_exptl_absorpt_correction_T_max  0.951
_exptl_absorpt_correction_T_min  0.797
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
        (compiled Aug  2 2013,16:46:58)
Analytical numeric absorption correction using a multifaceted crystal
                        model based on expressions derived by R.C. Clark & J.S.
        (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_description       plate
_exptl_crystal_F_000             2288
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.562
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details
;
 Flack x determined using 1204 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.006(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         3301
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0391
_refine_ls_R_factor_gt           0.0319
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0326P)^2^+3.4253P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0661
_refine_ls_wR_factor_ref         0.0702
_reflns_Friedel_coverage         0.736
_reflns_Friedel_fraction_full    0.955
_reflns_Friedel_fraction_max     0.773
_reflns_number_gt                2999
_reflns_number_total             3301
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6dt01674j2.cif
_cod_data_source_block           III-dz5b
_cod_database_code               7040204
_shelx_estimated_absorpt_t_min   0.751
_shelx_estimated_absorpt_t_max   0.951