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_7154944
_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         'C26 H25 N O2'
_chemical_formula_sum            'C26 H25 N O2'
_chemical_formula_weight         383.47
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.137(3)
_cell_length_b                   20.633(5)
_cell_length_c                   8.734(2)
_cell_measurement_reflns_used    8119
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      23.86
_cell_measurement_theta_min      1.97
_cell_volume                     2007.0(9)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0538
_diffrn_reflns_av_sigmaI/netI    0.0554
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            8119
_diffrn_reflns_theta_full        23.86
_diffrn_reflns_theta_max         23.86
_diffrn_reflns_theta_min         1.97
_exptl_absorpt_coefficient_mu    0.079
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.249
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rectangular
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.43
_exptl_crystal_size_min          0.35
_refine_diff_density_max         0.203
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -2(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         2870
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.010
_refine_ls_R_factor_all          0.0853
_refine_ls_R_factor_gt           0.0558
_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^)+(0.0778P)^2^+0.1730P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1346
_refine_ls_wR_factor_ref         0.1520
_reflns_number_gt                2023
_reflns_number_total             2870
_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_database_code               7154944