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_1548190
_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 unk
_chemical_formula_sum            'C37 H54 O3'
_chemical_formula_weight         546.80
_chemical_name_systematic
(2aS,4S,5'R,6aS,6bS,8aS,8bR,9S,10R,11aS,12aS,12bR)-5',6a,8a,9-tetramethyl-4-(4-p
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.8269(4)
_cell_length_b                   11.8121(7)
_cell_length_c                   39.687(3)
_cell_measurement_reflns_used    1686
_cell_measurement_temperature    290(2)
_cell_measurement_theta_max      60.0130
_cell_measurement_theta_min      4.3470
_cell_volume                     3200.4(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      290(2)
_diffrn_detector_area_resol_mean 15.9149
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.965
_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  0.0378
_diffrn_reflns_av_unetI/netI     0.0651
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -2
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       47
_diffrn_reflns_limit_l_min       -48
_diffrn_reflns_number            7688
_diffrn_reflns_point_group_measured_fraction_full 0.883
_diffrn_reflns_point_group_measured_fraction_max 0.862
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.835
_diffrn_reflns_theta_min         3.905
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.534
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90647
_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    1.135
_exptl_crystal_description       block
_exptl_crystal_F_000             1200
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.250
_refine_diff_density_max         0.137
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details
;
 Flack x determined using 1183 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     365
_refine_ls_number_reflns         5213
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0721
_refine_ls_R_factor_gt           0.0534
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0495P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1236
_refine_ls_wR_factor_ref         0.1450
_reflns_Friedel_coverage         0.550
_reflns_Friedel_fraction_full    0.747
_reflns_Friedel_fraction_max     0.722
_reflns_number_gt                3997
_reflns_number_total             5213
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            1.cif
_cod_data_source_block           1
_cod_original_cell_volume        3200.4(3)
_cod_database_code               1548190
_shelx_estimated_absorpt_t_min   0.831
_shelx_estimated_absorpt_t_max   0.878
_shelxl_version_number           2013-4
_shelx_res_checksum              72721
_shelx_hkl_checksum              29242