Advanced Nitroso Aldol Reaction: Metal-Free Cross-Coupling of Anilines with Silyl Enol Ethers en Route to α-Amino Ketones.
Ramakrishna, Isai; Bhajammanavar, Vinod; Mallik, Sumitava; Baidya, Mahiuddin; Organic letters 19 (2017) 516–519; doi:10.1021/acs.orglett.6b03686

data_1555998
_publ_section_title
;
 Advanced Nitroso Aldol Reaction: Metal-Free Cross-Coupling of Anilines
 with Silyl Enol Ethers en Route to \a-Amino Ketones.
;
_journal_issue                   3
_journal_name_full               'Organic letters'
_journal_page_first              516
_journal_page_last               519
_journal_paper_doi               10.1021/acs.orglett.6b03686
_journal_volume                  19
_journal_year                    2017
_chemical_formula_moiety         'C20 H12 F3 N3'
_chemical_formula_sum            'C20 H12 F3 N3'
_chemical_formula_weight         351.33
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 102.782(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.696(2)
_cell_length_b                   9.0705(14)
_cell_length_c                   15.811(3)
_cell_measurement_reflns_used    496
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      16.43
_cell_measurement_theta_min      2.61
_cell_volume                     1635.8(5)
_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-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0960
_diffrn_reflns_av_unetI/netI     0.1100
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9988
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        24.085
_diffrn_reflns_theta_max         24.085
_diffrn_reflns_theta_min         1.785
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_correction_T_min  0.973
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5(Bruker AXS.Inc)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_description       block
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.447
_refine_diff_density_min         -0.332
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       0.004(3)
_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   1.012
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         2579
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.012
_refine_ls_R_factor_all          0.1794
_refine_ls_R_factor_gt           0.0758
_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^)+(0.1294P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1970
_refine_ls_wR_factor_ref         0.2593
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1135
_reflns_number_total             2579
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b03686_si_004.cif
_cod_data_source_block           152
_cod_original_cell_volume        1635.7(5)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1555998
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.973
_shelx_estimated_absorpt_t_max   0.989
_shelx_res_checksum              2508
_shelx_hkl_checksum              20928