Simple access to 5-carboalkoxy-2,3-dihydro-4H-pyran-4-ones via domino acylative electrocyclization: First three step total synthesis of dihydronaphthopyran-4-one class of natural products
Ilangovan, Andivelu; Sakthivel, Palaniappan; RSC Adv.  (2014) –; doi:10.1039/C4RA11174E

data_7218539
_publ_section_title
;
 Simple access to 5-carboalkoxy-2,3-dihydro-4H-pyran-4-ones via domino
 acylative electrocyclization: First three step total synthesis of
 dihydronaphthopyran-4-one class of natural products
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C4RA11174E
_journal_year                    2014
_chemical_formula_moiety         'C14 H16 O4 S'
_chemical_formula_sum            'C14 H16 O4 S'
_chemical_formula_weight         280.33
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 91.972(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   10.4001(2)
_cell_length_b                   20.6610(6)
_cell_length_c                   13.5979(4)
_cell_measurement_reflns_used    3089
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      20.50
_cell_measurement_theta_min      2.19
_cell_volume                     2920.14(13)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.663
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0418
_diffrn_reflns_av_unetI/netI     0.0293
_diffrn_reflns_Laue_measured_fraction_full 0.663
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            18926
_diffrn_reflns_point_group_measured_fraction_full 0.663
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         21.890
_diffrn_reflns_theta_min         1.794
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.114
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    0.638
_exptl_crystal_description       PLATE
_exptl_crystal_F_000             592
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.09
_refine_diff_density_max         1.089
_refine_diff_density_min         -0.674
_refine_diff_density_rms         0.079
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     345
_refine_ls_number_reflns         3508
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.1063
_refine_ls_R_factor_gt           0.0842
_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^)+(0.1866P)^2^+3.2870P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2594
_refine_ls_wR_factor_ref         0.2886
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2570
_reflns_number_total             3508
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c4ra11174e2.cif
_cod_data_source_block           shelx
_cod_database_code               7218539
_shelxl_version_number           2014-3
_shelx_res_checksum              84036