Application of β-(2-Chloroaroyl) Thioacetanilides in Synthesis: An Unusual and Highly Efficient Access to Thiochromeno[2,3-b]pyridine Derivatives
Li-Rong Wen; Ji-Hui Sun; Ming Li; En-Tao Sun; Shu-Sheng Zhang; Journal of Organic Chemistry 73 (2008) 1852–1863; doi:10.1021/jo7024702

data_4023322
_publ_contact_author_address
;
Key Laboratory of Eco-Chemical Engineering, Ministry of Education, 
College of Chemistry and Molecular Engineering, 
Qingdao University of Science and Technology,
 Qingdao 266042, 
China
;
_publ_contact_author_email       liming928@qust.edu.cn
_publ_contact_author_fax         '+86 532 8402 3927'
_publ_contact_author_name        'Ming Li'
_publ_contact_author_phone       '+86 532 8402 2990'
_publ_section_title
;
 Application of \b-(2-Chloroaroyl) Thioacetanilides in Synthesis:
 An Unusual and Highly Efficient Access to
 Thiochromeno[2,3-b]pyridine Derivatives
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1852
_journal_page_last               1863
_journal_paper_doi               10.1021/jo7024702
_journal_volume                  73
_journal_year                    2008
_chemical_formula_moiety         'C27 H20 Cl N3 O5 S'
_chemical_formula_sum            'C27 H20 Cl N3 O5 S'
_chemical_formula_weight         533.97
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_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
_cell_angle_alpha                61.820(8)
_cell_angle_beta                 77.894(9)
_cell_angle_gamma                70.454(9)
_cell_formula_units_Z            2
_cell_length_a                   11.1920(9)
_cell_length_b                   11.2077(10)
_cell_length_c                   11.2808(11)
_cell_measurement_reflns_used    2710
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      25.0
_cell_measurement_theta_min      2.7
_cell_volume                     1173.14(18)
_computing_cell_refinement       CrystalClear
_computing_data_collection       CrystalClear
_computing_data_reduction        crystalclear
_computing_publication_material  'CrystalStructure 3.7.0'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      113(2)
_diffrn_detector_area_resol_mean 7.31
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Rigaku Saturn'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0484
_diffrn_reflns_av_sigmaI/netI    0.0823
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            14893
_diffrn_reflns_theta_full        27.88
_diffrn_reflns_theta_max         27.88
_diffrn_reflns_theta_min         2.05
_exptl_absorpt_coefficient_mu    0.299
_exptl_absorpt_correction_T_max  0.9881
_exptl_absorpt_correction_T_min  0.9650
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   crystalclear
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.512
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.392
_refine_diff_density_min         -0.401
_refine_diff_density_rms         0.117
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.964
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     343
_refine_ls_number_reflns         5558
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.964
_refine_ls_R_factor_all          0.0667
_refine_ls_R_factor_gt           0.0410
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0592P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0897
_refine_ls_wR_factor_ref         0.1099
_reflns_number_gt                3682
_reflns_number_total             5558
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo7024702-File002_2.cif
_cod_data_source_block           compound9b
_cod_original_sg_symbol_Hall     '-P 1 '
_cod_database_code               4023322