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_1549860
_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            'C9 H7 N O5'
_chemical_formula_weight         209.16
_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   geom
_audit_creation_method           SHELXL-2014/6
_audit_update_record
;
2017-11-08 deposited with the CCDC.
2018-08-29 downloaded from the CCDC.
;
_cell_angle_alpha                106.573(3)
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_cell_angle_gamma                94.501(3)
_cell_formula_units_Z            2
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_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.3994
_cell_measurement_theta_min      2.4572
_cell_volume                     437.69(4)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'Bruker APEX2'
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_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
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_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
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_diffrn_reflns_av_unetI/netI     0.0166
_diffrn_reflns_Laue_measured_fraction_full 0.995
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_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6864
_diffrn_reflns_point_group_measured_fraction_full 0.995
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_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.400
_diffrn_reflns_theta_min         2.457
_exptl_absorpt_coefficient_mu    0.132
_exptl_absorpt_correction_T_max  0.9485
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_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.587
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Lump
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_exptl_crystal_size_max          0.15
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
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_refine_ls_number_reflns         1777
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0302
_refine_ls_R_factor_gt           0.0283
_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^)+(0.0398P)^2^+0.1396P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0767
_refine_ls_wR_factor_ref         0.0786
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1657
_reflns_number_total             1777
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8sc03447h2.cif
_cod_data_source_block           170731LT_0m
_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.
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_cod_database_code               1549860
_shelxl_version_number           2014/6
_shelx_res_checksum              9278