Nickel catalyzed regio- and stereoselective arylation and methylation of allenamides via coupling reactions. An experimental and computational study
Liu, Yang; Cerveri, Alessandro; De Nisi, Assunta; Monari, Magda; Nieto Faza, Olalla; Lopez, Carlos Silva; Bandini, Marco; Organic Chemistry Frontiers 5 (2018) 3231–; doi:10.1039/C8QO00729B

data_1554396
_publ_section_title
;
 Nickel catalyzed regio- and stereoselective arylation and methylation of
 allenamides via coupling reactions. An experimental and computational
 study
;
_journal_issue                   22
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              3231
_journal_paper_doi               10.1039/C8QO00729B
_journal_volume                  5
_journal_year                    2018
_chemical_formula_sum            'C12 H26 Cl2 N2 Ni O7'
_chemical_formula_weight         439.96
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2018-01-17 deposited with the CCDC.
2018-10-05 downloaded from the CCDC.
;
_cell_angle_alpha                63.724(3)
_cell_angle_beta                 88.610(3)
_cell_angle_gamma                86.344(3)
_cell_formula_units_Z            2
_cell_length_a                   6.9966(10)
_cell_length_b                   12.0579(17)
_cell_length_c                   12.9998(18)
_cell_measurement_reflns_used    9822
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      31.91
_cell_measurement_theta_min      2.92
_cell_volume                     981.4(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0559
_diffrn_reflns_av_unetI/netI     0.0617
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            18734
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.971
_diffrn_reflns_theta_min         1.747
_exptl_absorpt_coefficient_mu    1.293
_exptl_absorpt_correction_T_max  0.932
_exptl_absorpt_correction_T_min  0.821
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            'pale green'
_exptl_crystal_density_diffrn    1.489
_exptl_crystal_description       platelet
_exptl_crystal_F_000             460
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.554
_refine_diff_density_min         -1.185
_refine_diff_density_rms         0.126
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     261
_refine_ls_number_reflns         6699
_refine_ls_number_restraints     9
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0746
_refine_ls_R_factor_gt           0.0594
_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^)+(0.1109P)^2^+0.2902P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1628
_refine_ls_wR_factor_ref         0.1738
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5369
_reflns_number_total             6699
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8qo00729b3.cif
_cod_data_source_block           shelx
_cod_database_code               1554396
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_min   0.782
_shelx_estimated_absorpt_t_max   0.938
_shelx_res_checksum              25923