Iron(II) Active Species in Iron-Bisphosphine Catalyzed Kumada and Suzuki-Miyaura Cross-Couplings of Phenyl Nucleophiles and Secondary Alkyl Halides.
Daifuku, Stephanie L.; Kneebone, Jared L.; Snyder, Benjamin E. R.; Neidig, Michael L.; Journal of the American Chemical Society 137 (2015) 11432–11444; doi:10.1021/jacs.5b06648

data_4129467
_publ_section_title
;
 Iron(II) Active Species in Iron-Bisphosphine Catalyzed Kumada and
 Suzuki-Miyaura Cross-Couplings of Phenyl Nucleophiles and Secondary Alkyl
 Halides.
;
_journal_issue                   35
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              11432
_journal_page_last               11444
_journal_paper_doi               10.1021/jacs.5b06648
_journal_volume                  137
_journal_year                    2015
_chemical_formula_moiety         'C68 H93 Br Fe P2, C4 H10 O'
_chemical_formula_sum            'C72 H103 Br Fe O P2'
_chemical_formula_weight         1182.24
_chemical_name_common            neijk42
_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   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   31.239(7)
_cell_length_b                   14.820(4)
_cell_length_c                   15.184(4)
_cell_measurement_reflns_used    4057
_cell_measurement_temperature    100.0(5)
_cell_measurement_theta_max      22.73
_cell_measurement_theta_min      2.32
_cell_volume                     7030(3)
_computing_cell_refinement       'SAINT (Bruker, 2014)'
_computing_data_collection       'APEX2 (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SIR2011 (Burla et al., 2012)'
_diffrn_ambient_temperature      100.0(5)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD platform'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1546
_diffrn_reflns_av_unetI/netI     0.1343
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            47332
_diffrn_reflns_point_group_measured_fraction_full 0.966
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_theta_full        25.028
_diffrn_reflns_theta_max         25.099
_diffrn_reflns_theta_min         1.870
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.867
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6336
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2014)'
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.117
_exptl_crystal_description       needle
_exptl_crystal_F_000             2536
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.411
_refine_diff_density_min         -0.520
_refine_diff_density_rms         0.075
_refine_ls_abs_structure_details
; 
 Flack x determined using 2290 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.037(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     770
_refine_ls_number_reflns         12010
_refine_ls_number_restraints     165
_refine_ls_restrained_S_all      1.005
_refine_ls_R_factor_all          0.1208
_refine_ls_R_factor_gt           0.0624
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0430P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1059
_refine_ls_wR_factor_ref         0.1258
_reflns_Friedel_coverage         0.857
_reflns_Friedel_fraction_full    0.932
_reflns_Friedel_fraction_max     0.924
_reflns_number_gt                7665
_reflns_number_total             12010
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja5b06648_si_003.cif
_cod_data_source_block           neijk42
_cod_database_code               4129467
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.745
_shelx_estimated_absorpt_t_max   0.918
_shelx_res_checksum              30532
_shelx_hkl_checksum              72672