Modulating the Reactivity of Functionalized N,S-Ketene Acetal in MCR: Selective Synthesis of Tetrahydropyridines and Thiochromeno[2,3-b]pyridines via DABCO-Catalyzed Tandem Annulation
Li-Rong Wen; Yong-Jie Shi; Guang-Yuan Liu; Ming Li; Journal of Organic Chemistry 77 (2012) 4252–4260; doi:10.1021/jo202665q

data_4027170
_publ_section_title
;
 Modulating the Reactivity of Functionalized N,S-Ketene Acetal in MCR:
 Selective Synthesis of Tetrahydropyridines and
 Thiochromeno[2,3-b]pyridines via DABCO-Catalyzed Tandem Annulation
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4252
_journal_page_last               4260
_journal_paper_doi               10.1021/jo202665q
_journal_volume                  77
_journal_year                    2012
_chemical_formula_moiety         'C31 H20 Cl2 N2 O2 S'
_chemical_formula_sum            'C31 H20 Cl2 N2 O2 S'
_chemical_formula_weight         555.45
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 92.392(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.5186(18)
_cell_length_b                   17.509(4)
_cell_length_c                   15.532(3)
_cell_measurement_reflns_used    4629
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.75
_cell_volume                     2586.3(9)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'XP in Siemens SHELXTL (Sheldrick, 1994)'
_computing_publication_material  'SHELX97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       '\w scans at fixed \c = 45\%'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0285
_diffrn_reflns_av_sigmaI/netI    0.0400
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            12180
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         2.46
_exptl_absorpt_coefficient_mu    0.365
_exptl_absorpt_correction_T_max  0.8983
_exptl_absorpt_correction_T_min  0.8385
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_description       block
_exptl_crystal_F_000             1144
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.291
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.160
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     343
_refine_ls_number_reflns         5896
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.160
_refine_ls_R_factor_all          0.0688
_refine_ls_R_factor_gt           0.0606
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0425P)^2^+1.7413P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1286
_refine_ls_wR_factor_ref         0.1339
_reflns_number_gt                5324
_reflns_number_total             5896
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo202665q_si_002.cif
_cod_data_source_block           sa995
_cod_original_cell_volume        2586.2(9)
_cod_database_code               4027170