Pd-Catalyzed One-Pot Stepwise Synthesis of Benzo[b][1,6]naphthyridines from 2-Chloroquinoline-3-carbonitriles Using Sulfur and Amines As Nucleophiles.
Kumar, Ritush; Asthana, Mrityunjaya; Singh, Radhey M.; The Journal of organic chemistry 82 (2017) 11531–11542; doi:10.1021/acs.joc.7b02147

data_4033002
_publ_section_title
;
 Pd-Catalyzed One-Pot Stepwise Synthesis of Benzo[b][1,6]naphthyridines
 from 2-Chloroquinoline-3-carbonitriles Using Sulfur and Amines As
 Nucleophiles.
;
_journal_issue                   21
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              11531
_journal_page_last               11542
_journal_paper_doi               10.1021/acs.joc.7b02147
_journal_volume                  82
_journal_year                    2017
_chemical_formula_moiety         'C25 H18 N2 S'
_chemical_formula_sum            'C25 H18 N2 S'
_chemical_formula_weight         378.47
_chemical_name_common            rk
_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                90.000(5)
_cell_angle_beta                 90.000(5)
_cell_angle_gamma                90.000(5)
_cell_formula_units_Z            4
_cell_length_a                   10.261(5)
_cell_length_b                   10.261(5)
_cell_length_c                   18.417(5)
_cell_measurement_reflns_used    938
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.7889
_cell_measurement_theta_min      3.3119
_cell_volume                     1939.1(14)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0938
_diffrn_measured_fraction_theta_full 0.950
_diffrn_measured_fraction_theta_max 0.623
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_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  0.0161
_diffrn_reflns_av_sigmaI/netI    0.0442
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4461
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.85
_diffrn_reflns_theta_min         3.57
_exptl_absorpt_coefficient_mu    0.179
_exptl_absorpt_correction_T_max  0.880
_exptl_absorpt_correction_T_min  0.815
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_density_meas      1.256
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rectangular
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.424
_exptl_crystal_size_mid          0.323
_exptl_crystal_size_min          0.242
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.034
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.915
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3157
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.915
_refine_ls_R_factor_all          0.0887
_refine_ls_R_factor_gt           0.0529
_refine_ls_shift/su_max          0.032
_refine_ls_shift/su_mean         0.004
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0779P)^2^+0.6537P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1265
_refine_ls_wR_factor_ref         0.1520
_reflns_number_gt                2094
_reflns_number_total             3157
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            jo7b02147_si_002.cif
_cod_data_source_block           rk-sch2ph_compound_3a
_cod_depositor_comments
'Adding full bibliography for 4033002--4033004.cif.'
_cod_database_code               4033002