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_4033004
_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_sum            'C21 H19 N3'
_chemical_formula_weight         313.39
_space_group_IT_number           1
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      1
_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                76.25(16)
_cell_angle_beta                 85.06(12)
_cell_angle_gamma                86.46(16)
_cell_formula_units_Z            2
_cell_length_a                   9.405(15)
_cell_length_b                   9.59(2)
_cell_length_c                   9.930(13)
_cell_measurement_reflns_used    2020
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      32.3216
_cell_measurement_theta_min      3.0426
_cell_volume                     866(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0938
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0342
_diffrn_reflns_av_sigmaI/netI    0.0528
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            9516
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.02
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_correction_T_min  0.983
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlisPro, Agilent Technologies'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.202
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             332.0
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.166
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.983
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     433
_refine_ls_number_reflns         4135
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      0.983
_refine_ls_R_factor_all          0.0845
_refine_ls_R_factor_gt           0.0514
_refine_ls_shift/su_max          1.819
_refine_ls_shift/su_mean         0.372
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0785P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0545
_refine_ls_wR_factor_ref         0.1773
_reflns_number_gt                2716
_reflns_number_total             6116[3058]
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            jo7b02147_si_002.cif
_cod_data_source_block           rkipr_compound_9c
_cod_depositor_comments
'Adding full bibliography for 4033002--4033004.cif.'
_cod_database_code               4033004