Copper catalyzed photoredox synthesis of α-keto esters, quinoxaline, and naphthoquinone: controlled oxidation of terminal alkynes to glyoxals.
Das, Deb Kumar; Kumar Pampana, V. Kishore; Hwang, Kuo Chu; Chemical science 9 (2018) 7318–7326; doi:10.1039/c8sc03447h

data_1549861
_publ_section_title
;
 Copper catalyzed photoredox synthesis of \a-keto esters, quinoxaline, and
 naphthoquinone: controlled oxidation of terminal alkynes to glyoxals.
;
_journal_issue                   37
_journal_name_full               'Chemical science'
_journal_page_first              7318
_journal_page_last               7326
_journal_paper_doi               10.1039/c8sc03447h
_journal_volume                  9
_journal_year                    2018
_chemical_formula_sum            'C12 H12 Cu N2 O6'
_chemical_formula_weight         343.78
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/6
_audit_update_record
;
2018-06-05 deposited with the CCDC.
2018-08-29 downloaded from the CCDC.
;
_cell_angle_alpha                76.038(2)
_cell_angle_beta                 85.125(2)
_cell_angle_gamma                72.2290(10)
_cell_formula_units_Z            1
_cell_length_a                   5.0866(4)
_cell_length_b                   7.5068(5)
_cell_length_c                   9.0684(6)
_cell_measurement_reflns_used    4579
_cell_measurement_temperature    99(2)
_cell_measurement_theta_max      26.7016
_cell_measurement_theta_min      2.9258
_cell_volume                     319.98(4)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_diffrn_ambient_temperature      99(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.990
_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  0.0132
_diffrn_reflns_av_unetI/netI     0.0117
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            5170
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.702
_diffrn_reflns_theta_min         2.926
_exptl_absorpt_coefficient_mu    1.738
_exptl_absorpt_correction_T_max  0.95
_exptl_absorpt_correction_T_min  0.78
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.784
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       tabullar
_exptl_crystal_F_000             175
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.394
_refine_diff_density_min         -0.290
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.160
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     98
_refine_ls_number_reflns         1351
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.160
_refine_ls_R_factor_all          0.0172
_refine_ls_R_factor_gt           0.0172
_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^)+(0.0118P)^2^+0.2585P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0442
_refine_ls_wR_factor_ref         0.0442
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1349
_reflns_number_total             1351
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8sc03447h2.cif
_cod_data_source_block           mo_170824lt_0m_a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 

 Adding full bibliography for 1549859--1549861.cif.
;
_cod_database_code               1549861
_shelxl_version_number           2014/6
_shelx_res_checksum              21984