Ni-Catalyzed Reductive Dicarbofunctionalization of Nonactivated Alkenes: Scope and Mechanistic Insights.
Shu, Wei; García-Domínguez, Andrés; Quirós, M Teresa; Mondal, Rahul; Cárdenas, Diego J; Nevado, Cristina; Journal of the American Chemical Society 141 (2019) 13812–13821; doi:10.1021/jacs.9b02973

data_4128821
_publ_section_title
;
 Ni-Catalyzed Reductive Dicarbofunctionalization of Nonactivated Alkenes:
 Scope and Mechanistic Insights.
;
_journal_issue                   35
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              13812
_journal_page_last               13821
_journal_paper_doi               10.1021/jacs.9b02973
_journal_volume                  141
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C35 H49 N O8'
_chemical_formula_sum            'C35 H49 N O8'
_chemical_formula_weight         611.75
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_Hall           'P -2yac'
_space_group_name_H-M_alt        'P 1 n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2017/1
_cell_angle_alpha                90
_cell_angle_beta                 91.1868(8)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   16.03406(16)
_cell_length_b                   5.88869(5)
_cell_length_c                   18.24264(14)
_cell_measurement_reflns_used    19469
_cell_measurement_temperature    160(2)
_cell_measurement_theta_max      74.1770
_cell_measurement_theta_min      3.6820
_cell_volume                     1722.09(3)
_computing_cell_refinement
'CrysAlisPro, Version 1.171.38.46 (Rigaku Oxford Diffraction, 2017)'
_computing_data_collection
'CrysAlisPro, Version 1.171.38.46 (Rigaku Oxford Diffraction, 2017)'
_computing_data_reduction
'CrysAlisPro, Version 1.171.38.46 (Rigaku Oxford Diffraction, 2017)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  'SHELXL-2017 and PLATON (Spek, 2015)'
_computing_structure_refinement  'SHELXL-2017 (Sheldrick, 2015b)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2015a)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      160(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 10.3801
_diffrn_detector_type            'Atlas CCD area detector on \k goniostat'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'four-circle \k-geometry diffractometer'
_diffrn_measurement_device_type
'Oxford Diffraction SuperNova, dual radiation diffractometer'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0166
_diffrn_reflns_av_unetI/netI     0.0115
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            31164
_diffrn_reflns_point_group_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.132
_diffrn_reflns_theta_min         3.633
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray source'
_exptl_absorpt_coefficient_mu    0.672
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88250
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Empirical absorption correction using spherical harmonics,
implemented in the SCALE3 ABSPACK scaling algorithm.
CrysAlisPro, Version 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.180
_exptl_crystal_description       prism
_exptl_crystal_F_000             660
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.148
_refine_diff_density_min         -0.131
_refine_diff_density_rms         0.025
_refine_ls_abs_structure_details
;
 Flack x determined using 3112 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.04(3)
_refine_ls_extinction_coef       0.0010(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL (Sheldrick, 2015)'
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     481
_refine_ls_number_reflns         6728
_refine_ls_number_restraints     158
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0284
_refine_ls_R_factor_gt           0.0278
_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^)+(0.0459P)^2^+0.1871P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0755
_refine_ls_wR_factor_ref         0.0766
_reflns_Friedel_coverage         0.924
_reflns_Friedel_fraction_full    0.941
_reflns_Friedel_fraction_max     0.923
_reflns_number_gt                6607
_reflns_number_total             6728
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b02973_si_002.cif
_cod_data_source_block           NV1732
_cod_original_sg_symbol_H-M      'P n'
_cod_database_code               4128821
_shelx_shelxl_version_number     2017/1
_oxdiff_exptl_absorpt_empirical_full_min 0.839
_oxdiff_exptl_absorpt_empirical_full_max 1.326
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_shelx_res_checksum              83221
_shelx_hkl_checksum              67099