α,β-Functionalization of Saturated Ketones with Anthranils via Cu-Catalyzed Sequential Dehydrogenation/Aza-Michael Addition/Annulation Cascade Reactions in One-Pot
Tiwari, Dharmendra Kumar; Tiwari, Dipak Kumar; Mandalaparthi, Phanindrudu; Wakade, Sandip Balasaheb; Nanubolu, Jagadeesh Babu; Chem. Commun.  (2017) –; doi:10.1039/C7CC01195D

data_7119985
_publ_section_title
;
 \a,\b-Functionalization of Saturated Ketones with Anthranils via
 Cu-Catalyzed Sequential Dehydrogenation/Aza-Michael Addition/Annulation
 Cascade Reactions in One-Pot
;
_journal_name_full               'Chem. Commun.'
_journal_paper_doi               10.1039/C7CC01195D
_journal_year                    2017
_chemical_formula_moiety         'C22 H14 Cl N O'
_chemical_formula_sum            'C22 H14 Cl N O'
_chemical_formula_weight         343.79
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2017-01-06 deposited with the CCDC.
2017-04-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.4770(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.8090(9)
_cell_length_b                   13.9475(11)
_cell_length_c                   10.4695(8)
_cell_measurement_reflns_used    3833
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.27
_cell_measurement_theta_min      2.44
_cell_volume                     1721.2(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_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, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0347
_diffrn_reflns_av_unetI/netI     0.0252
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            16319
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.262
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.230
_exptl_absorpt_correction_T_max  0.964
_exptl_absorpt_correction_T_min  0.946
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker AXS SADABS program'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_description       block
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.160
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.357
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3033
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.357
_refine_ls_R_factor_all          0.0892
_refine_ls_R_factor_gt           0.0815
_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^)+(0.0356P)^2^+1.3730P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1504
_refine_ls_wR_factor_ref         0.1539
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2754
_reflns_number_total             3033
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7cc01195d2.cif
_cod_data_source_block           BE25
_cod_database_code               7119985
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.947
_shelx_estimated_absorpt_t_max   0.964
_exptl_absorpt_special_details
'Sheldrick,G.M.,(2003),University of gottingen,Germany'
_shelx_res_checksum              39862