General and Mild Nickel-Catalyzed Cyanation of Aryl/Heteroaryl Chlorides with Zn(CN)<sub>2</sub>: Key Roles of DMAP.
Zhang, Xingjie; Xia, Aiyou; Chen, Haoyi; Liu, Yuanhong; Organic letters 19 (2017) 2118–2121; doi:10.1021/acs.orglett.7b00732

data_1556036
_publ_section_title
;
 General and Mild Nickel-Catalyzed Cyanation of Aryl/Heteroaryl Chlorides
 with Zn(CN)<sub>2</sub>: Key Roles of DMAP.
;
_journal_issue                   8
_journal_name_full               'Organic letters'
_journal_page_first              2118
_journal_page_last               2121
_journal_paper_doi               10.1021/acs.orglett.7b00732
_journal_volume                  19
_journal_year                    2017
_chemical_formula_sum            'C28 H44 Cl2 N8 Ni O2'
_chemical_formula_weight         654.32
_space_group_crystal_system      cubic
_space_group_IT_number           229
_space_group_name_Hall           '-I 4 2 3'
_space_group_name_H-M_alt        'I m -3 m'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            6
_cell_length_a                   17.0714(11)
_cell_length_b                   17.0714(11)
_cell_length_c                   17.0714(11)
_cell_measurement_reflns_used    2028
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      39.862
_cell_measurement_theta_min      4.771
_cell_volume                     4975.2(6)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0637
_diffrn_reflns_av_unetI/netI     0.0238
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            14388
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.445
_diffrn_reflns_theta_min         1.687
_exptl_absorpt_coefficient_mu    0.784
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6104
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             2076
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.329
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.215
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     56
_refine_ls_number_reflns         496
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.215
_refine_ls_R_factor_all          0.0577
_refine_ls_R_factor_gt           0.0505
_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^)+(0.0894P)^2^+0.8352P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1387
_refine_ls_wR_factor_ref         0.1448
_reflns_Friedel_coverage         0.000
_reflns_number_gt                423
_reflns_number_total             496
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b00732_si_002.cif
_cod_data_source_block           cd16600
_cod_original_cell_volume        4975.2(10)
_cod_database_code               1556036
_shelx_estimated_absorpt_t_min   0.859
_shelx_estimated_absorpt_t_max   0.919
_shelxl_version_number           2013-4
_shelx_res_checksum              23749
_shelx_hkl_checksum              33716