Cross-dehydrogenative regioselective Csp(3)-Csp(2) coupling of enamino-ketones followed by rearrangement: an amazing formation route to acridine-1,8-dione derivatives.
Sarkar, Rajib; Mukhopadhyay, Chhanda; Organic & biomolecular chemistry 14 (2016) 2706–2715; doi:10.1039/c5ob02655e

data_7154945
_publ_section_title
;
 Cross-dehydrogenative regioselective Csp(3)-Csp(2) coupling of
 enamino-ketones followed by rearrangement: an amazing formation route to
 acridine-1,8-dione derivatives.
;
_journal_issue                   9
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2706
_journal_page_last               2715
_journal_paper_doi               10.1039/c5ob02655e
_journal_volume                  14
_journal_year                    2016
_chemical_formula_moiety         'C21 H22 Cl N O2'
_chemical_formula_sum            'C21 H22 Cl N O2'
_chemical_formula_weight         355.85
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2015-11-27 deposited with the CCDC.
2016-01-27 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 92.530(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.1242(17)
_cell_length_b                   16.492(4)
_cell_length_c                   15.175(4)
_cell_measurement_reflns_used    6620
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.70
_cell_measurement_theta_min      1.82
_cell_volume                     1781.2(8)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.944
_diffrn_measured_fraction_theta_max 0.944
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0422
_diffrn_reflns_av_sigmaI/netI    0.0452
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6620
_diffrn_reflns_theta_full        22.70
_diffrn_reflns_theta_max         22.70
_diffrn_reflns_theta_min         1.82
_exptl_absorpt_coefficient_mu    0.229
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rectangular
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.27
_refine_diff_density_max         0.192
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.950
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         2259
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.950
_refine_ls_R_factor_all          0.0557
_refine_ls_R_factor_gt           0.0414
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0586P)^2^+0.6186P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1006
_refine_ls_wR_factor_ref         0.1116
_reflns_number_gt                1765
_reflns_number_total             2259
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5ob02655e2.cif
_cod_data_source_block           a
_cod_depositor_comments
'Adding full bibliography for 7154944--7154945.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7154945