Practical carbon?carbon bond formation from olefins through nickel-catalyzed reductive olefin hydrocarbonation
Xi Lu; Bin Xiao; Zhenqi Zhang; Tianjun Gong; Wei Su; Jun Yi; Yao Fu; Lei Liu; Nature Communications 7 (2016) 11129–; doi:10.1038/ncomms11129

data_1548191
_publ_section_title
;
 Practical carbon?carbon bond formation from olefins through
 nickel-catalyzed reductive olefin hydrocarbonation
;
_journal_name_full               'Nature Communications'
_journal_page_first              11129
_journal_paper_doi               10.1038/ncomms11129
_journal_volume                  7
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_sum            'C34 H50 Cl N3 O4 S Si'
_chemical_formula_weight         660.37
_chemical_name_systematic
(1S,2S,4S,5R)-2-((R)-quinolin-4-yl((trimethylsilyl)oxy)methyl)-5-(2-(1-tosylpipe
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_cell_angle_alpha                90
_cell_angle_beta                 108.3160(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.19700(10)
_cell_length_b                   11.95510(10)
_cell_length_c                   14.1022(2)
_cell_measurement_reflns_used    12364
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      69.7520
_cell_measurement_theta_min      3.6930
_cell_volume                     1792.10(4)
_computing_cell_refinement       'CrysAlisPro (Agilent Technologies)'
_computing_data_collection       'CrysAlisPro (Agilent Technologies)'
_computing_data_reduction        'CrysAlisPro (Agilent Technologies)'
_computing_molecular_graphics    'Ortep-3 (L. J. Farrugia, 2001)'
_computing_publication_material  SHELXL-2013
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      291(2)
_diffrn_detector_area_resol_mean 15.9149
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Gemini S Ultra, Agilent Technologies'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0235
_diffrn_reflns_av_unetI/netI     0.0261
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            16620
_diffrn_reflns_point_group_measured_fraction_full 0.955
_diffrn_reflns_point_group_measured_fraction_max 0.942
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.785
_diffrn_reflns_theta_min         3.301
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.121
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71289
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.224
_exptl_crystal_description       block
_exptl_crystal_F_000             708
_exptl_crystal_size_max          0.290
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.250
_refine_diff_density_max         1.245
_refine_diff_density_min         -0.390
_refine_diff_density_rms         0.103
_refine_ls_abs_structure_details
;
 Flack x determined using 2819 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.080(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     420
_refine_ls_number_reflns         6375
_refine_ls_number_restraints     19
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.0866
_refine_ls_R_factor_gt           0.0854
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1662P)^2^+3.1465P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2767
_refine_ls_wR_factor_ref         0.2802
_reflns_Friedel_coverage         0.815
_reflns_Friedel_fraction_full    0.911
_reflns_Friedel_fraction_max     0.892
_reflns_number_gt                6349
_reflns_number_total             6375
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            2.cif
_cod_data_source_block           2
_cod_original_cell_volume        1792.10(3)
_cod_database_code               1548191
_shelx_estimated_absorpt_t_min   0.578
_shelx_estimated_absorpt_t_max   0.619
_shelxl_version_number           2013-4
_shelx_res_checksum              9118
_shelx_hkl_checksum              86564