Mechanistic Implications for the Ni(I)-Catalyzed Kumada Cross-Coupling Reaction
Iffland, L.; Petuker, A.; Van Gastel, M.; Apfel, U.-P.; Inorganics 5 (2017) 78–; doi:10.3390/inorganics5040078

data_1556551
_publ_section_title
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 Mechanistic Implications for the Ni(I)-Catalyzed Kumada Cross-Coupling
 Reaction
;
_journal_name_full               Inorganics
_journal_page_first              78
_journal_paper_doi               10.3390/inorganics5040078
_journal_volume                  5
_journal_year                    2017
_chemical_formula_moiety         'C41 H39 I Ni P3'
_chemical_formula_sum            'C41 H39 I Ni P3'
_chemical_formula_weight         810.24
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   20.5260(16)
_cell_length_b                   10.3670(6)
_cell_length_c                   17.0858(10)
_cell_measurement_reflns_used    16191
_cell_measurement_temperature    170
_cell_measurement_theta_max      23.0060
_cell_measurement_theta_min      3.0110
_cell_volume                     3635.7(4)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      170
_diffrn_detector_area_resol_mean 8.4171
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.835
_diffrn_measurement_details
;
  1 omega -129.50   68.50   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -30.0000    1.0000  290.0000 198

  2 omega  -79.00  117.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       20.0000   11.0000  280.0000 196

  3 phi    300.00  330.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
   0.0000  -40.0000 -109.0000     -     30

  4 omega  -24.50   34.50   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       20.0000   91.0000   90.0000 59

  5 omega   32.00  138.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       40.0000 -179.0000  340.0000 106

  6 omega  -16.50  111.50   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       20.0000   51.0000  300.0000 128

  7 phi    130.00  160.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
   0.0000  -40.0000    1.0000     -     30

  8 omega  -68.00   68.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -30.0000   71.0000    0.0000 136

  9 omega -123.00   15.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -30.0000  -29.0000   60.0000 138

 10 phi    200.00  230.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
   0.0000   30.0000   21.0000     -     30

 11 omega   -6.00  122.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       30.0000   51.0000  270.0000 128

 12 omega   -8.00  128.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       30.0000   71.0000  330.0000 136

 13 omega -109.00   -7.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.0000  141.0000    0.0000 102
;
_diffrn_measurement_device_type  'Xcalibur, Sapphire2, large Be window'
_diffrn_measurement_method       '\w and \p scans'
_diffrn_orient_matrix_UB_11      -0.0308952000
_diffrn_orient_matrix_UB_12      -0.0083824000
_diffrn_orient_matrix_UB_13      0.0137380000
_diffrn_orient_matrix_UB_21      0.0155428000
_diffrn_orient_matrix_UB_22      -0.0190991000
_diffrn_orient_matrix_UB_23      0.0262434000
_diffrn_orient_matrix_UB_31      0.0010023000
_diffrn_orient_matrix_UB_32      0.0358638000
_diffrn_orient_matrix_UB_33      0.0171975000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1807
_diffrn_reflns_av_unetI/netI     0.1939
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.835
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            109489
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.835
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         36.624
_diffrn_reflns_theta_min         3.037
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.543
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77372
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.480
_exptl_crystal_description       prism
_exptl_crystal_F_000             1644
_refine_diff_density_max         1.537
_refine_diff_density_min         -1.362
_refine_diff_density_rms         0.115
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   -0.09(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.941
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     417
_refine_ls_number_reflns         14073
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.941
_refine_ls_R_factor_all          0.2132
_refine_ls_R_factor_gt           0.0787
_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^)+(0.0841P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1646
_refine_ls_wR_factor_ref         0.2167
_reflns_Friedel_coverage         0.950
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.836
_reflns_number_gt                6136
_reflns_number_total             14073
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            Inorganics-2017-5-78.cif
_cod_data_source_block           li274
_cod_database_code               1556551
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 1.09(3)
 -0.09(3)
2. 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
3.a Secondary CH2 refined with riding coordinates:
 C013(H01A,H01B), C01C(H01C,H01D), C02Z(H02C,H02D)
3.b Aromatic/amide H refined with riding coordinates:
 C00W(H00W), C011(H011), C012(H012), C01D(H01E), C01J(H01J), C01P(H01P),
 C01Y(H01Y), C01Z(H01Z), C020(H020), C028(H028), C02A(H02A), C02B(H02B),
 C02H(H02H), C02R(H02R), C03H(H03H), C03L(H03L), C03R(H03R), C03V(H03V),
 C03X(H03X), C044(H044), C045(H045), C046(H046), C048(H048), C049(H049),
 C04E(H04E), C04J(H04J), C04O(H04O), C04P(H04P), C04X(H04X), C051(H051)
3.c Idealised Me refined as rotating group:
 C047(H04A,H04B,H04C)
;