Silver-Catalyzed Tandem Synthesis of Naphthyridines and Thienopyridines via Three-Component Reaction
Akhilesh K. Verma; Siva K. Reddy Kotla; Deepak Choudhary; Monika Patel; Rakesh K. Tiwari; Journal of Organic Chemistry 78 (2013) 4386–4401; doi:10.1021/jo400400c

data_4028212
_publ_section_title
;
 Silver-Catalyzed Tandem Synthesis of Naphthyridines and Thienopyridines
 via Three-Component Reaction
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4386
_journal_page_last               4401
_journal_paper_doi               10.1021/jo400400c
_journal_volume                  78
_journal_year                    2013
_chemical_formula_sum            'C24 H21 Br N2 O'
_chemical_formula_weight         433.34
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 96.405(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.5885(7)
_cell_length_b                   12.0366(5)
_cell_length_c                   16.3904(10)
_cell_measurement_temperature    293(2)
_cell_volume                     2075.9(2)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.881
_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  0.0358
_diffrn_reflns_av_sigmaI/netI    0.0442
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            17806
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         29.09
_diffrn_reflns_theta_min         3.33
_exptl_absorpt_coefficient_mu    10.666
_exptl_crystal_density_diffrn    2.163
_exptl_crystal_F_000             1254
_refine_diff_density_max         0.586
_refine_diff_density_min         -0.625
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         4915
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.999
_refine_ls_R_factor_all          0.1038
_refine_ls_R_factor_gt           0.0585
_refine_ls_shift/su_max          0.012
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0779P)^2^+1.4275P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1428
_refine_ls_wR_factor_ref         0.1657
_reflns_number_gt                3080
_reflns_number_total             4915
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo400400c_si_002.cif
_cod_data_source_block           shelxl
_cod_database_code               4028212