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_7156194
_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         'C25 H24 O5'
_chemical_formula_sum            'C25 H24 O5'
_chemical_formula_weight         404.44
_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_creation_method           SHELXL-97
_audit_update_record
;
2018-01-10 deposited with the CCDC.
2018-04-11 downloaded from the CCDC.
;
_cell_angle_alpha                70.558(2)
_cell_angle_beta                 75.621(2)
_cell_angle_gamma                79.609(2)
_cell_formula_units_Z            2
_cell_length_a                   7.7460(3)
_cell_length_b                   11.9902(4)
_cell_length_c                   12.4618(4)
_cell_measurement_reflns_used    111
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.40
_cell_measurement_theta_min      1.77
_cell_volume                     1051.15(7)
_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-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi omega scans'
_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  0.0311
_diffrn_reflns_av_sigmaI/netI    0.0349
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            18333
_diffrn_reflns_theta_full        28.40
_diffrn_reflns_theta_max         28.40
_diffrn_reflns_theta_min         1.77
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.982
_exptl_absorpt_correction_T_min  0.982
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       square
_exptl_crystal_F_000             428.0
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.23
_refine_diff_density_max         1.220
_refine_diff_density_min         -0.406
_refine_diff_density_rms         0.137
_refine_ls_extinction_coef       0.079(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     274
_refine_ls_number_reflns         5230
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.1170
_refine_ls_R_factor_gt           0.0762
_refine_ls_shift/su_max          0.013
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1720P)^2^+0.1103P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2420
_refine_ls_wR_factor_ref         0.2808
_reflns_number_gt                3082
_reflns_number_total             5230
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c8ob00718g2.cif
_cod_data_source_block           ups3238na_mw_m1_0m
_cod_depositor_comments
'Adding full bibliography for 7156193--7156194.cif.'
_cod_original_cell_volume        1051.15(6)
_cod_database_code               7156194