Copper Catalyzed Oxidative C-C Bond Cleavage of 1,2-Diketones: A Divergent Approach to 1,8-Naphthalimides, Biphenyl-2,2'-dicarboxamides, and N-Heterocyclic Amides.
Sakhare, Priyanka R.; Subramanian, Parthasarathi; Kaliappan, Krishna P.; The Journal of organic chemistry 84 (2019) 2112–2125; doi:10.1021/acs.joc.8b03114

data_4033786
_publ_section_title
;
 Copper Catalyzed Oxidative C-C Bond Cleavage of 1,2-Diketones:
 A&#x00A0;Divergent Approach to 1,8-Naphthalimides,
 Biphenyl-2,2'-dicarboxamides, and N-Heterocyclic Amides.
;
_journal_issue                   4
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              2112
_journal_page_last               2125
_journal_paper_doi               10.1021/acs.joc.8b03114
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C18 H9 F3 N2 O2'
_chemical_formula_sum            'C18 H9 F3 N2 O2'
_chemical_formula_weight         342.27
_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'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2016-12-20
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2015.10.28 svn.r3245 for OlexSys, GUI svn.r5128)
;
_cell_angle_alpha                90
_cell_angle_beta                 111.783(13)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.4306(10)
_cell_length_b                   19.0359(18)
_cell_length_c                   8.6514(10)
_cell_measurement_reflns_used    3501
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      30.3090
_cell_measurement_theta_min      2.3020
_cell_volume                     1442.2(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w   -110.00  19.00   0.50   12.00    --  -20.00 -72.00-108.00  258
  2  \w    -36.00  59.50   0.50   12.00    --  -20.00  72.00  36.00  191
  3  \w    -13.50  18.00   0.50   12.00    --  -20.00 -72.00 108.00   63
  4  \w    -49.00  70.00   0.50   12.00    --  -20.00  72.00 -36.00  238
  5  \w    -59.00 -23.00   0.50   12.00    --  -20.00  72.00-108.00   72
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0758162000
_diffrn_orient_matrix_UB_12      -0.0074512000
_diffrn_orient_matrix_UB_13      -0.0070963000
_diffrn_orient_matrix_UB_21      -0.0145642000
_diffrn_orient_matrix_UB_22      0.0364800000
_diffrn_orient_matrix_UB_23      0.0020260000
_diffrn_orient_matrix_UB_31      -0.0242926000
_diffrn_orient_matrix_UB_32      0.0014372000
_diffrn_orient_matrix_UB_33      -0.0880217000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0718
_diffrn_reflns_av_unetI/netI     0.0610
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            10913
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.990
_diffrn_reflns_theta_max         24.990
_diffrn_reflns_theta_min         2.140
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.131
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.30777
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.576
_exptl_crystal_description       plate
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.383
_exptl_crystal_size_mid          0.074
_exptl_crystal_size_min          0.017
_refine_diff_density_max         0.279
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         2536
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0843
_refine_ls_R_factor_gt           0.0556
_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^)+(0.0525P)^2^+0.9700P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1210
_refine_ls_wR_factor_ref         0.1419
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1826
_reflns_number_total             2536
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b03114_si_002.cif
_cod_data_source_block           kpk-125-ps-215-a_mo
_cod_database_code               4033786
_chemical_oxdiff_formula         C17H10N2O2F3
_reflns_odcompleteness_completeness 91.58
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     31.10
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C13(H13), C4(H4), C5(H5), C15(H15), C9(H9), C11(H11), C2(H2), C10(H10),
 C14(H14)
;
_shelx_res_checksum              71768
_shelx_hkl_checksum              2213
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.621
_oxdiff_exptl_absorpt_empirical_full_min 0.608