Ni-Catalyzed Reductive Coupling of Alkyl Acids with Unactivated Tertiary Alkyl and Glycosyl Halides.
Zhao, Chenglong; Jia, Xiao; Wang, Xuan; Gong, Hegui; Journal of the American Chemical Society  (2014) 141204123340001–; doi:10.1021/ja510653n

data_4123048
_publ_section_title
;
 Ni-Catalyzed Reductive Coupling of Alkyl Acids with Unactivated Tertiary
 Alkyl and Glycosyl Halides.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              141204123340001
_journal_paper_doi               10.1021/ja510653n
_journal_year                    2014
_chemical_formula_moiety         'C22 H26 O'
_chemical_formula_sum            'C22 H26 O'
_chemical_formula_weight         306.43
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2014-11-19
_audit_creation_method
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_cell_angle_alpha                90
_cell_angle_beta                 90.386(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.7302(10)
_cell_length_b                   10.1147(9)
_cell_length_c                   16.0345(15)
_cell_measurement_reflns_used    3956
_cell_measurement_temperature    130
_cell_measurement_theta_max      30.52
_cell_measurement_theta_min      2.29
_cell_volume                     1740.2(3)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      130
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0283
_diffrn_reflns_av_unetI/netI     0.0318
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            17225
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.592
_diffrn_reflns_theta_min         2.277
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.069
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6865
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0457 before and 0.0403 after correction.
The Ratio of minimum to maximum transmission is 0.9201.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.170
_exptl_crystal_description       block
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.455
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         5325
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0831
_refine_ls_R_factor_gt           0.0554
_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^)+(0.0651P)^2^+0.5816P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1391
_refine_ls_wR_factor_ref         0.1573
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3689
_reflns_number_total             5325
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja510653n_si_002.cif
_cod_data_source_block           mo_dm14666_0m
_cod_database_code               4123048
_shelxl_version_number           2014-3
_shelx_estimated_absorpt_t_max   0.988
_shelx_estimated_absorpt_t_min   0.982
_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:
 C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B), C11(H11A,H11B), C12(H12A,H12B), C14(H14A,H14B),
 C15(H15A,H15B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C18(H18), C19(H19), C20(H20),
 C21(H21), C22(H22)
2.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
;
_shelx_res_checksum              46898
_shelx_hkl_checksum              86887
_olex2_submission_special_instructions 'No special instructions were received'