Vilsmeier Cyclization of α-Acetyl-α-aroyl Ketene-N, S-Acetals: Direct and Efficient Synthesis of Halogenated Pyridin-2(1H)-ones
yu, haifeng; zhang, yongmei; li, tiechun; liao, peiqiu; diao, quanping; xin, guang; meng, qingling; hou, dongyan; RSC Adv.  (2015) –; doi:10.1039/C4RA14626C

data_7219284
_publ_section_title
;
 Vilsmeier Cyclization of \a-Acetyl-\a-aroyl Ketene-N, S-Acetals: Direct
 and Efficient Synthesis of Halogenated Pyridin-2(1H)-ones
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C4RA14626C
_journal_year                    2015
_chemical_formula_sum            'C20 H20 N O2 S'
_chemical_formula_weight         338.43
_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-2013
_audit_update_record
;
2013-11-30 deposited with the CCDC.
2015-01-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.181(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.3829(15)
_cell_length_b                   9.3060(11)
_cell_length_c                   17.3055(19)
_cell_measurement_temperature    293(2)
_cell_volume                     1809.7(4)
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.983
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0446
_diffrn_reflns_av_unetI/netI     0.0680
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            8153
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.519
_diffrn_reflns_theta_min         1.812
_exptl_absorpt_coefficient_mu    0.190
_exptl_crystal_density_diffrn    1.242
_exptl_crystal_F_000             716
_refine_diff_density_max         1.187
_refine_diff_density_min         -0.595
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         4089
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.1016
_refine_ls_R_factor_gt           0.0757
_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^)+(0.1456P)^2^+0.3164P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2080
_refine_ls_wR_factor_ref         0.2389
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2864
_reflns_number_total             4089
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c4ra14626c2.cif
_cod_data_source_block           shelx
_cod_database_code               7219284
_shelxl_version_number           2013-4
_shelx_res_checksum              28614
_shelx_hkl_checksum              58055