Mechanistic Study of an Improved Ni Precatalyst for Suzuki-Miyaura Reactions of Aryl Sulfamates: Understanding the Role of Ni(I) Species.
Mohadjer Beromi, Megan; Nova, Ainara; Balcells, David; Brasacchio, Ann M.; Brudvig, Gary W.; Guard, Louise M.; Hazari, Nilay; Vinyard, David J.; Journal of the American Chemical Society 139 (2017) 922–936; doi:10.1021/jacs.6b11412

data_4125760
_publ_section_title
;
 Mechanistic Study of an Improved Ni Precatalyst for Suzuki-Miyaura
 Reactions of Aryl Sulfamates: Understanding the Role of Ni(I) Species.
;
_journal_issue                   2
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              922
_journal_page_last               936
_journal_paper_doi               10.1021/jacs.6b11412
_journal_volume                  139
_journal_year                    2017
_chemical_formula_moiety         'C34 H28 Br Fe Ni P2, 2(C4 H8 O)'
_chemical_formula_sum            'C42 H44 Br Fe Ni O2 P2'
_chemical_formula_weight         837.18
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2014-02-11
_audit_creation_method
;
Olex2 1.2
(compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736)
;
_cell_angle_alpha                111.252(8)
_cell_angle_beta                 101.106(7)
_cell_angle_gamma                96.437(7)
_cell_formula_units_Z            2
_cell_length_a                   9.4430(4)
_cell_length_b                   14.1318(6)
_cell_length_c                   15.9349(11)
_cell_measurement_reflns_used    22837
_cell_measurement_temperature    161
_cell_measurement_theta_max      23.8
_cell_measurement_theta_min      3.1
_cell_volume                     1905.9(2)
_computing_cell_refinement
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_data_collection
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_data_reduction
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      161
_diffrn_detector                 'Image Plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'Rigaku IP'
_diffrn_measured_fraction_theta_full 0.846
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID imaging plate'
_diffrn_measurement_method       '\w scans'
_diffrn_measurement_specimen_support Loop
_diffrn_orient_matrix_type       FS_PROCESS
_diffrn_orient_matrix_UB_11      0.080447
_diffrn_orient_matrix_UB_12      -0.012262
_diffrn_orient_matrix_UB_13      -0.032949
_diffrn_orient_matrix_UB_21      -0.035853
_diffrn_orient_matrix_UB_22      -0.076493
_diffrn_orient_matrix_UB_23      -0.023136
_diffrn_orient_matrix_UB_31      -0.066101
_diffrn_orient_matrix_UB_32      0.000891
_diffrn_orient_matrix_UB_33      -0.056746
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0626
_diffrn_reflns_av_unetI/netI     0.0386
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            33701
_diffrn_reflns_point_group_measured_fraction_full 0.846
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         23.812
_diffrn_reflns_theta_min         3.141
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           40.0
_diffrn_source_power             2.0
_diffrn_source_target            Mo
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    2.042
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.542
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private Communication'
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.459
_exptl_crystal_description       Block
_exptl_crystal_F_000             862
_exptl_crystal_recrystallization_method 'THF/Pentane, -35C'
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.757
_refine_diff_density_min         -0.529
_refine_diff_density_rms         0.085
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     442
_refine_ls_number_reflns         5838
_refine_ls_number_restraints     389
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.0637
_refine_ls_R_factor_gt           0.0509
_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^)+(0.0499P)^2^+5.4891P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1161
_refine_ls_wR_factor_ref         0.1226
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4887
_reflns_number_total             5838
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja6b11412_si_002.cif
_cod_data_source_block           '_dppfNiIBr'
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' according to
/home/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
;
_cod_database_code               4125760
_shelxl_version_number           2013-4
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 C42-C41 \\sim C38-C37
 with sigma of 0.02
 C41-C40 \\sim C37-C36
 with sigma of 0.02
 C40-C39 \\sim C36-C35
 with sigma of 0.02
 O2-C39 \\sim O1-C35
 with sigma of 0.02
 O2-C42 \\sim O1-C38
 with sigma of 0.02
 C41-O2 \\sim C37-O1
 with sigma of 0.02
 C40-O2 \\sim C36-O1
 with sigma of 0.02
 C42-C39 \\sim C38-C35
 with sigma of 0.02
3. Rigid bond restraints
 Br1, P1, P2, C22, C19, C17, C4, C5, C1, C2, C20, C7, C8, C9, C10, C12, C34,
 Ni1, Fe6, C13, C6, C3, C16, C24, C25, C23, C15, C29, C18, C14, C21, C11, C28,
 C26, C27, C33, C32, C31, C30
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
Br1 \\sim P1 \\sim P2 \\sim C28 \\sim C26 \\sim C27 \\sim C4 \\sim C5 \\sim C1
\\sim C2 \\sim C7 \\sim C8 \\sim C9 \\sim C10 \\sim C12 \\sim C34 \\sim C33
\\sim C32 \\sim Ni1 \\sim C6 \\sim C3 \\sim C24 \\sim C25 \\sim C23 \\sim C29
\\sim C31 \\sim C30 \\sim C11 \\sim C22 \\sim C19 \\sim C17 \\sim C20 \\sim Fe6
\\sim C13 \\sim C16 \\sim C15 \\sim C18 \\sim C14 \\sim C21: within 1.7A with
sigma of 0.04 and sigma for terminal atoms of 0.08
5.a Secondary CH2 refined with riding coordinates:
 C42(H42A,H42B), C40(H40A,H40B), C41(H41A,H41B), C39(H39A,H39B), C37(H37A,
 H37B), C35(H35A,H35B), C38(H38A,H38B), C36(H36A,H36B)
5.b Aromatic/amide H refined with riding coordinates:
 C22(H22), C19(H19), C17(H17), C28(H28), C26(H26), C27(H27), C4(H4), C5(H5),
 C2(H2), C20(H20), C8(H8), C9(H9), C10(H10), C12(H12), C34(H34), C33(H33),
 C32(H32), C6(H6), C3(H3), C16(H16), C24(H24), C25(H25), C15(H15), C31(H31),
 C30(H30), C14(H14), C21(H21), C11(H11)
;
_shelx_res_checksum              4976
_shelx_hkl_checksum              10190