Nickel-Catalyzed Regiodivergent Cyanation of Allylic Alcohols: Scope, Mechanism, and Application to the Synthesis of 1,n-Dinitriles
Long, Jinguo; Xia, Shaomiao; Wang, Ting; Cheng, Gui-Juan; Fang, Xianjie; ACS Catalysis 11 (2021) 13880–13890; doi:10.1021/acscatal.1c03729

data_4519165
_publ_section_title
;
 Nickel-Catalyzed Regiodivergent Cyanation of Allylic Alcohols: Scope,
 Mechanism, and Application to the Synthesis of 1,n-Dinitriles
;
_journal_issue                   22
_journal_name_full               'ACS Catalysis'
_journal_page_first              13880
_journal_page_last               13890
_journal_paper_doi               10.1021/acscatal.1c03729
_journal_volume                  11
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C19 H18 N2'
_chemical_formula_sum            'C19 H18 N2'
_chemical_formula_weight         274.35
_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'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 90.139(16)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.693(2)
_cell_length_b                   7.6997(14)
_cell_length_c                   17.596(4)
_cell_measurement_reflns_used    4081
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      67.81
_cell_measurement_theta_min      2.51
_cell_volume                     771.3(4)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      297(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0927
_diffrn_reflns_av_unetI/netI     0.1107
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            7823
_diffrn_reflns_point_group_measured_fraction_full 0.953
_diffrn_reflns_point_group_measured_fraction_max 0.951
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.048
_diffrn_reflns_theta_min         2.511
_exptl_absorpt_coefficient_mu    0.536
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.181
_exptl_crystal_description       block
_exptl_crystal_F_000             292
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.120
_exptl_transmission_factor_max   0.7530
_exptl_transmission_factor_min   0.6505
_refine_diff_density_max         0.145
_refine_diff_density_min         -0.158
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details
;
 Flack x determined using 639 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.3(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2682
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.1057
_refine_ls_R_factor_gt           0.0392
_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^)+(0.0592P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1027
_refine_ls_wR_factor_ref         0.1169
_reflns_Friedel_coverage         0.773
_reflns_Friedel_fraction_full    0.904
_reflns_Friedel_fraction_max     0.902
_reflns_number_gt                1843
_reflns_number_total             2682
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs1c03729_si_002.cif
_cod_data_source_block           t_a
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_absolute_configuration' value 'AD' was changed
to 'ad' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_original_cell_volume        771.4(3)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4519165
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.919
_shelx_estimated_absorpt_t_max   0.939
_shelx_res_checksum              15876
_shelx_hkl_checksum              15240