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_4033785
_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         'C24 H18 N4 O2, C12 H10 N2 O'
_chemical_formula_sum            'C36 H28 N6 O3'
_chemical_formula_weight         592.64
_space_group_crystal_system      orthorhombic
_space_group_IT_number           18
_space_group_name_Hall           'P 2 2ab'
_space_group_name_H-M_alt        'P 21 21 2'
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   20.1905(9)
_cell_length_b                   15.9988(6)
_cell_length_c                   9.2004(3)
_cell_measurement_reflns_used    8029
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      30.9720
_cell_measurement_theta_min      2.2210
_cell_volume                     2971.9(2)
_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 0.996
_diffrn_measured_fraction_theta_max 0.996
_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    8.00    --  -20.00 -72.00 -36.00  258
  2  \w    -58.00   5.00   0.50    8.00    --  -20.00  72.00-108.00  126
  3  \w   -110.00 -76.50   0.50    8.00    --  -20.00 -72.00-108.00   67
;
_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      0.0088913000
_diffrn_orient_matrix_UB_12      -0.0101050000
_diffrn_orient_matrix_UB_13      0.0724882000
_diffrn_orient_matrix_UB_21      0.0000201000
_diffrn_orient_matrix_UB_22      0.0430832000
_diffrn_orient_matrix_UB_23      0.0181698000
_diffrn_orient_matrix_UB_31      -0.0339920000
_diffrn_orient_matrix_UB_32      -0.0025681000
_diffrn_orient_matrix_UB_33      0.0189532000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0450
_diffrn_reflns_av_unetI/netI     0.0528
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            12525
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        24.987
_diffrn_reflns_theta_max         24.987
_diffrn_reflns_theta_min         2.214
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.43018
_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    1.325
_exptl_crystal_description       block
_exptl_crystal_F_000             1240
_exptl_crystal_size_max          0.307
_exptl_crystal_size_mid          0.164
_exptl_crystal_size_min          0.099
_refine_diff_density_max         0.329
_refine_diff_density_min         -0.346
_refine_diff_density_rms         0.062
_refine_ls_abs_structure_details
;
 Flack x determined using 1783 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.9(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     406
_refine_ls_number_reflns         5176
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0483
_refine_ls_R_factor_gt           0.0417
_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^)+(0.0499P)^2^+0.3638P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0964
_refine_ls_wR_factor_ref         0.1015
_reflns_Friedel_coverage         0.753
_reflns_Friedel_fraction_full    0.981
_reflns_Friedel_fraction_max     0.981
_reflns_number_gt                4702
_reflns_number_total             5176
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b03114_si_001.cif
_cod_data_source_block           kpk-125-ps-198_mo
_cod_database_code               4033785
_chemical_oxdiff_formula         C23H23N5O2
_reflns_odcompleteness_completeness 93.53
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     31.04
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N3(H3), N6(H6), N2(H2), C35(H35), C21(H21), C11(H11), C36(H36), C34(H34),
 C14(H14), C24(H24), C15(H15), C4(H4), C17(H17), C22(H22), C10(H10), C9(H9),
 C8(H8), C23(H23), N5(H5), C33(H33), C2(H2A), C16(H16), C28(H28), C3(H3A),
 C1(H1), C27(H27), C26(H26), C25(H25)
;
_shelx_res_checksum              48263
_shelx_hkl_checksum              42205
_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 1.916
_oxdiff_exptl_absorpt_empirical_full_min 0.647