Nickel-Catalyzed Alkylation and Transfer Hydrogenation of α,β-Unsaturated Enones with Methanol
Castellanos-Blanco, Nahury; Flores-Alamo, Marcos; García, Juventino J.; Organometallics 31 (2012) 680–; doi:10.1021/om2010222

data_4068035
_publ_section_title
;
 Nickel-Catalyzed Alkylation and Transfer Hydrogenation of
 \a,\b-Unsaturated Enones with Methanol
;
_journal_issue                   2
_journal_name_full               Organometallics
_journal_page_first              680
_journal_paper_doi               10.1021/om2010222
_journal_volume                  31
_journal_year                    2012
_chemical_absolute_configuration syn
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C31 H46 Ni1 O1 P2'
_chemical_formula_sum            'C31 H46 Ni O P2'
_chemical_formula_weight         555.33
_chemical_name_systematic
;
 [(dippe)Ni(\h2-C\a,C\b-dibenzylideneacetone)]
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_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
_audit_creation_date             2010-09-23T14:28:24-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.4669(4)
_cell_length_b                   9.5163(3)
_cell_length_c                   20.2315(12)
_cell_measurement_reflns_used    8445
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      25.9923
_cell_measurement_theta_min      3.5324
_cell_measurement_wavelength     0.71073
_cell_volume                     2977.8(2)
_computing_cell_refinement
;
        CrysAlisPro, Oxford Diffraction Ltd.,
        Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
        (compiled Apr 28 2010,14:27:37)
;
_computing_data_collection
;
        CrysAlisPro, Oxford Diffraction Ltd.,
        Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
        (compiled Apr 28 2010,14:27:37)
;
_computing_data_reduction
;
        CrysAlisPro, Oxford Diffraction Ltd.,
        Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
        (compiled Apr 28 2010,14:27:37)
;
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      130(2)
_diffrn_detector_area_resol_mean 10.4685
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0121228
_diffrn_orient_matrix_UB_12      0.0596878
_diffrn_orient_matrix_UB_13      -0.0187296
_diffrn_orient_matrix_UB_21      0.0421059
_diffrn_orient_matrix_UB_22      -0.0282251
_diffrn_orient_matrix_UB_23      -0.0040268
_diffrn_orient_matrix_UB_31      -0.0135791
_diffrn_orient_matrix_UB_32      -0.0342603
_diffrn_orient_matrix_UB_33      -0.0293561
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0393
_diffrn_reflns_av_unetI/netI     0.0432
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            13341
_diffrn_reflns_theta_full        26.08
_diffrn_reflns_theta_max         26.08
_diffrn_reflns_theta_min         3.54
_exptl_absorpt_coefficient_mu    0.78
_exptl_absorpt_correction_T_max  0.873
_exptl_absorpt_correction_T_min  0.841
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
        CrysAlisPro, Oxford Diffraction Ltd.,
        Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
        (compiled Apr 28 2010,14:27:37)
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            black
_exptl_crystal_density_diffrn    1.239
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1192
_exptl_crystal_size_max          0.3034
_exptl_crystal_size_mid          0.2246
_exptl_crystal_size_min          0.2064
_refine_diff_density_max         0.305
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.006(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.974
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     324
_refine_ls_number_reflns         5132
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.974
_refine_ls_R_factor_all          0.0338
_refine_ls_R_factor_gt           0.0279
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0325P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0592
_refine_ls_wR_factor_ref         0.0602
_reflns_number_gt                4507
_reflns_number_total             5132
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            om2010222_si_002.cif
_cod_data_source_block           2b
_cod_original_formula_sum        'C31 H46 Ni1 O1 P2 '
_cod_database_code               4068035