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_4033784
_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         'C20 H17 N3 O2'
_chemical_formula_sum            'C20 H17 N3 O2'
_chemical_formula_weight         331.36
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2018-02-01
_audit_creation_method
;
Olex2 1.2-ac3
(compiled 2017.02.24 svn.r3390 for Rigaku Oxford Diffraction, GUI svn.r5318)
;
_cell_angle_alpha                90
_cell_angle_beta                 109.569(19)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.0461(18)
_cell_length_b                   17.852(3)
_cell_length_c                   8.7609(14)
_cell_measurement_reflns_used    2367
_cell_measurement_temperature    150
_cell_measurement_theta_max      27.1660
_cell_measurement_theta_min      1.9890
_cell_volume                     1627.8(5)
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)'
_computing_data_collection       'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)'
_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      150
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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    -48.00  49.00   0.50   10.00    --  -20.00  72.00 -36.00  194
  2  \w    -42.50  25.00   0.50   10.00    --  -20.00  72.00 108.00  135
  3  \w    -35.00  -5.00   0.50   10.00    --  -20.00 -72.00 108.00   60
  4  \w   -110.00  19.00   0.50   10.00    --  -20.00 -72.00-180.00  258
  5  \w    -98.00 -83.50   0.50   10.00    --  -20.00 -72.00  36.00   29
;
_diffrn_measurement_device       'AFC12 (Right): Kappa 3 circle'
_diffrn_measurement_device_type  'Rigaku Saturn724+ (2x2 bin mode)'
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0578193000
_diffrn_orient_matrix_UB_12      -0.0209790000
_diffrn_orient_matrix_UB_13      -0.0249969000
_diffrn_orient_matrix_UB_21      0.0360290000
_diffrn_orient_matrix_UB_22      -0.0335543000
_diffrn_orient_matrix_UB_23      0.0075478000
_diffrn_orient_matrix_UB_31      0.0029447000
_diffrn_orient_matrix_UB_32      -0.0033013000
_diffrn_orient_matrix_UB_33      0.0818353000
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1067
_diffrn_reflns_av_unetI/netI     0.1139
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            10180
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         2.265
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'Rotating Anode'
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.36579
_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            'light yellow'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_description       needle
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.203
_exptl_crystal_size_mid          0.085
_exptl_crystal_size_min          0.043
_refine_diff_density_max         0.008
_refine_diff_density_min         -0.001
_refine_diff_density_rms         0.000
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.193
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     231
_refine_ls_number_reflns         2861
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.193
_refine_ls_R_factor_all          0.1674
_refine_ls_R_factor_gt           0.0986
_refine_ls_shift/su_max          0.014
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1235P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2474
_refine_ls_wR_factor_ref         0.2961
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1551
_reflns_number_total             2861
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b03114_si_003.cif
_cod_data_source_block           kpk-144-ps-101_mo
_cod_database_code               4033784
_shelx_shelxl_version_number     2014/7
_reflns_odcompleteness_completeness 90.51
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.93
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C10(H10), C4(H4), C17(H17), C15(H15), C16(H16), C9(H9), C6(H6), C3(H3)
2.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C12(H12A,H12B,H12C), C1(H1A,H1B,H1C)
;
_shelx_res_checksum              33463
_shelx_hkl_checksum              58331
_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 3.494
_oxdiff_exptl_absorpt_empirical_full_min 0.363