One-pot synthesis of 1,5-diketones from 3-acetyl-4-hydroxycoumarin and effective cyclization to unexpected 3,4-dihydropyridines.
Waheed, Mohd; Ahmed, Naseem; Alsharif, Meshari A.; Alahmdi, Mohammed Issa; Mukhtar, Sayeed; Organic & biomolecular chemistry 16 (2018) 3428–3437; doi:10.1039/c8ob00718g

data_7156193
_publ_section_title
;
 One-pot synthesis of 1,5-diketones from 3-acetyl-4-hydroxycoumarin and
 effective cyclization to unexpected 3,4-dihydropyridines.
;
_journal_issue                   18
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3428
_journal_page_last               3437
_journal_paper_doi               10.1039/c8ob00718g
_journal_volume                  16
_journal_year                    2018
_chemical_formula_moiety         'C24 H21 N O3, C2 H3 N'
_chemical_formula_sum            'C26 H24 N2 O3'
_chemical_formula_weight         412.47
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_block_doi                 10.5517/ccdc.csd.cc1ywzkc
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2018-01-02 deposited with the CCDC.
2018-04-11 downloaded from the CCDC.
;
_cell_angle_alpha                89.432(3)
_cell_angle_beta                 71.763(3)
_cell_angle_gamma                86.136(3)
_cell_formula_units_Z            2
_cell_length_a                   8.0151(4)
_cell_length_b                   11.4152(5)
_cell_length_c                   12.7980(6)
_cell_measurement_reflns_used    111
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.378
_cell_measurement_theta_min      1.675
_cell_volume                     1109.52(9)
_computing_cell_refinement       'Bruker Kappa Apex'
_computing_data_collection       'Bruker Kappa Apex'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0418
_diffrn_reflns_av_unetI/netI     0.0654
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            17926
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.378
_diffrn_reflns_theta_min         1.675
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.982
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_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.235
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       square
_exptl_crystal_F_000             436.0
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.23
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_refine_diff_density_max         0.461
_refine_diff_density_min         -0.817
_refine_diff_density_rms         0.144
_refine_ls_extinction_coef       0.0085(12)
_refine_ls_extinction_method     SHELXL
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         5535
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.950
_refine_ls_R_factor_all          0.1632
_refine_ls_R_factor_gt           0.0701
_refine_ls_shift/su_max          0.029
_refine_ls_shift/su_mean         0.022
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1827P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2155
_refine_ls_wR_factor_ref         0.2979
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2545
_reflns_number_total             5535
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c8ob00718g2.cif
_cod_data_source_block           shelx
_cod_depositor_comments
'Adding full bibliography for 7156193--7156194.cif.'
_cod_database_code               7156193
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.982
_shelx_estimated_absorpt_t_max   0.982
_shelx_res_checksum              33669