Copper-catalyzed synthesis of α-amino nitriles through methyl transfer from DMF to aromatic amines.
Yuan, Zaifeng; Li, Na; Zhu, Chunyu; Xia, Chengfeng; Chemical communications (Cambridge, England) 54 (2018) 2854–2857; doi:10.1039/c8cc00485d

data_7121273
_publ_section_title
;
 Copper-catalyzed synthesis of \a-amino nitriles through methyl transfer
 from DMF to aromatic amines.
;
_journal_issue                   23
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              2854
_journal_page_last               2857
_journal_paper_doi               10.1039/c8cc00485d
_journal_volume                  54
_journal_year                    2018
_chemical_formula_moiety         'C12 H12 N2 O'
_chemical_formula_sum            'C12 H12 N2 O'
_chemical_formula_weight         200.24
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2018-01-19 deposited with the CCDC.
2018-02-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.787(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.4481(12)
_cell_length_b                   7.0131(8)
_cell_length_c                   13.7142(16)
_cell_measurement_reflns_used    7425
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.88
_cell_measurement_theta_min      2.27
_cell_volume                     990.3(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-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.936
_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  0.0230
_diffrn_reflns_av_unetI/netI     0.0204
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.936
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            10505
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.936
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.988
_diffrn_reflns_theta_min         2.274
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_description       block
_exptl_crystal_F_000             424
_exptl_crystal_size_max          1.150
_exptl_crystal_size_mid          1.050
_exptl_crystal_size_min          0.340
_exptl_transmission_factor_max   0.4335
_exptl_transmission_factor_min   0.3956
_refine_diff_density_max         0.440
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       0.076(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         2948
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.094
_refine_ls_R_factor_all          0.0397
_refine_ls_R_factor_gt           0.0370
_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^)+(0.0555P)^2^+0.2717P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1014
_refine_ls_wR_factor_ref         0.1038
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2724
_reflns_number_total             2948
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8cc00485d2.cif
_cod_data_source_block           mo_xcf4085_0m
_cod_depositor_comments          'Adding full bibliography for 7121273.cif.'
_cod_database_code               7121273
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.906
_shelx_estimated_absorpt_t_max   0.971
_shelx_res_checksum              46879