Ni-Catalyzed Reductive Homocoupling of Unactivated Alkyl Bromides at Room Temperature and Its Synthetic Application
Yu Peng; Long Luo; Chang-Song Yan; Jian-Jian Zhang; Ya-Wen Wang; Journal of Organic Chemistry 78 (2013) 10960–10967; doi:10.1021/jo401936v

data_4028734
_publ_contact_author_name
;
;
_publ_section_title
;
 Ni-Catalyzed Reductive Homocoupling of Unactivated Alkyl Bromides at Room
 Temperature and Its Synthetic Application
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              10960
_journal_page_last               10967
_journal_paper_doi               10.1021/jo401936v
_journal_volume                  78
_journal_year                    2013
_chemical_formula_moiety         'C18 H23 N2 O4'
_chemical_formula_sum            'C18 H23 N2 O4'
_chemical_formula_weight         331.38
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-08-14
_audit_creation_method
;
  Olex2 1.2
  (compiled Apr 23 2013 17:54:37, GUI svn.r4466)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   14.8934(8)
_cell_length_b                   11.7913(6)
_cell_length_c                   19.2041(18)
_cell_measurement_reflns_used    3173
_cell_measurement_temperature    301.19(10)
_cell_measurement_theta_max      70.5690
_cell_measurement_theta_min      5.3030
_cell_volume                     3372.5(4)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SUPERFLIP, J. Appl. Cryst. (2007) 40, 786-790'
_diffrn_ambient_temperature      301.19(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.9387
_diffrn_measured_fraction_theta_max 0.9899
_diffrn_measurement_details
;
  1 omega  -55.00  -17.50   1.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -38.0000    0.0000 25

  2 omega  -78.00  -49.50   1.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  178.0000    0.0000 19

  3 omega  -69.00  -36.00   1.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  178.0000  -30.0000 22

  4 omega -108.00  -81.00   1.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  -38.0000  150.0000 18

  5 omega   94.00  125.50   1.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   38.0000  120.0000 21

  6 omega  103.00  128.50   1.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   38.0000  -60.0000 17

  7 omega   27.00   78.00   1.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000  -57.0000 -120.0000 34

  8 omega   26.00   62.00   1.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   38.0000  -60.0000 24

  9 omega   27.00   90.00   1.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   38.0000  120.0000 42

 10 omega   39.00  115.50   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000 -180.0000 51

 11 omega  104.00  143.00   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -77.0000 -120.0000 26

 12 omega   55.00   94.00   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -77.0000 -120.0000 26

 13 omega   44.00  104.00   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -50.0000  -30.0000 40

 14 omega   84.00  135.00   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   38.0000  -30.0000 34

 15 omega   42.00   85.50   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -38.0000 -180.0000 29

 16 omega   45.00   78.00   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -38.0000  120.0000 22

 17 omega  126.00  151.50   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   63.0000  -30.0000 17

 18 omega   87.00  114.00   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   63.0000  -30.0000 18

 19 omega   45.00   70.50   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -63.0000 -150.0000 17

 20 omega  129.00  178.50   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   38.0000  -90.0000 33

 21 omega   40.00   73.00   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000    0.0000 22

 22 omega   87.00  141.00   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   63.0000 -150.0000 36

 23 omega  132.00  168.00   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   38.0000    0.0000 24
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0434922000
_diffrn_orient_matrix_UB_12      -0.0934679000
_diffrn_orient_matrix_UB_13      -0.0447085000
_diffrn_orient_matrix_UB_21      -0.0198033000
_diffrn_orient_matrix_UB_22      0.0691179000
_diffrn_orient_matrix_UB_23      -0.0663983000
_diffrn_orient_matrix_UB_31      0.0917681000
_diffrn_orient_matrix_UB_32      0.0592415000
_diffrn_orient_matrix_UB_33      0.0068528000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0299
_diffrn_reflns_av_unetI/netI     0.0265
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            10791
_diffrn_reflns_theta_full        69.50
_diffrn_reflns_theta_max         70.06
_diffrn_reflns_theta_min         4.61
_diffrn_source                   'SuperNova (Cu) x-ray Source'
_exptl_absorpt_coefficient_mu    0.758
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81969
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_description       block
_exptl_crystal_F_000             1416
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.259
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       0.00059(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     222
_refine_ls_number_reflns         3193
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0499
_refine_ls_R_factor_gt           0.0379
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0567P)^2^+0.4675P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0988
_refine_ls_wR_factor_ref         0.1085
_reflns_number_gt                2550
_reflns_number_total             3193
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo401936v_si_005.cif
_cod_data_source_block           luol0108
_cod_database_code               4028734
_reflns_odcompleteness_completeness 93.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_olex2_refinement_description
;
1. 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
2.a Ternary CH refined with riding coordinates:
 C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C17(H17A,H17B)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C12(H12), C14(H14), C16(H16)
2.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C1A(H1AA,H1AB,
 H1AC)
;