Copper-catalyzed coupling of anthranils and α-keto acids: direct synthesis of α-ketoamides.
Li, Ping-Gui; Zhu, Hao; Fan, Min; Yan, Cheng; Shi, Kai; Chi, Xi-Wen; Zou, Liang-Hua; Organic & biomolecular chemistry 17 (2019) 5902–5907; doi:10.1039/c9ob00822e

data_7156877
_publ_section_title
;
 Copper-catalyzed coupling of anthranils and \a-keto acids: direct
 synthesis of \a-ketoamides.
;
_journal_issue                   24
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5902
_journal_page_last               5907
_journal_paper_doi               10.1039/c9ob00822e
_journal_volume                  17
_journal_year                    2019
_chemical_formula_sum            'C15 H11 N O3'
_chemical_formula_weight         253.25
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2018-11-16 deposited with the CCDC.    2019-05-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.8593(8)
_cell_length_b                   14.1412(10)
_cell_length_c                   6.7109(5)
_cell_measurement_reflns_used    3767
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.52
_cell_measurement_theta_min      3.17
_cell_volume                     1220.35(15)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_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  0.0244
_diffrn_reflns_av_unetI/netI     0.0292
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            5786
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         3.168
_exptl_absorpt_coefficient_mu    0.097
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_description       block
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.170
_refine_diff_density_max         0.149
_refine_diff_density_min         -0.169
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details
;
 Flack x determined using 817 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.4(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2105
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.096
_refine_ls_R_factor_all          0.0343
_refine_ls_R_factor_gt           0.0310
_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^)+(0.0428P)^2^+0.1561P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0792
_refine_ls_wR_factor_ref         0.0812
_reflns_Friedel_coverage         0.805
_reflns_Friedel_fraction_full    0.973
_reflns_Friedel_fraction_max     0.973
_reflns_number_gt                1984
_reflns_number_total             2105
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ob00822e2.cif
_cod_data_source_block           1_a
_cod_depositor_comments          'Adding full bibliography for 7156877.cif.'
_cod_database_code               7156877
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.979
_shelx_estimated_absorpt_t_max   0.984
_shelx_res_checksum              16377
_shelx_hkl_checksum              14478