TBHP mediated oxidation of N-2-alkynylphenyl α-amino carbonyl compounds to oxalic amides using visible light photoredox catalysis and their application in the synthesis of 2-aryl indoles
Liu, Wei; Liu, Sheng; Xie, Hongqi; Qing, Zhixing; Zeng, Jianguo; Cheng, Pi; RSC Adv. 5 (2015) 17383–; doi:10.1039/C4RA17232A

data_7219534
_publ_section_title
;
 TBHP mediated oxidation of N-2-alkynylphenyl \a-amino carbonyl compounds
 to oxalic amides using visible light photoredox catalysis and their
 application in the synthesis of 2-aryl indoles
;
_journal_issue                   23
_journal_name_full               'RSC Adv.'
_journal_page_first              17383
_journal_paper_doi               10.1039/C4RA17232A
_journal_volume                  5
_journal_year                    2015
_chemical_formula_moiety         'C18 H13 Cl F N O3'
_chemical_formula_sum            'C18 H13 Cl F N O3'
_chemical_formula_weight         345.74
_chemical_name_common            2q
_chemical_name_systematic
'ethyl 2-((4-chloro-2-((4-fluorophenyl)ethynyl)phenyl)amino)-2-oxoacetate'
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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-97
_audit_update_record
;
2014-12-29 deposited with the CCDC.
2015-02-09 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 95.570(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.191(2)
_cell_length_b                   4.4973(7)
_cell_length_c                   25.988(4)
_cell_measurement_reflns_used    2193
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.17
_cell_measurement_theta_min      2.65
_cell_volume                     1650.8(4)
_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-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(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_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0691
_diffrn_reflns_av_sigmaI/netI    0.0647
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            15559
_diffrn_reflns_theta_full        28.30
_diffrn_reflns_theta_max         28.30
_diffrn_reflns_theta_min         1.57
_exptl_absorpt_coefficient_mu    0.257
_exptl_absorpt_correction_T_max  0.9873
_exptl_absorpt_correction_T_min  0.8404
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.70
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.382
_refine_diff_density_min         -0.358
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         4056
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0986
_refine_ls_R_factor_gt           0.0596
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0428P)^2^+1.0682P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1059
_refine_ls_wR_factor_ref         0.1197
_reflns_number_gt                2803
_reflns_number_total             4056
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ra17232a2.cif
_cod_data_source_block           mo_chengp1_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_cell_volume        1650.7(4)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7219534