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_4033003
_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            'C23 H21 N3 O2'
_chemical_formula_weight         371.43
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_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                 95.082(5)
_cell_angle_gamma                90.000(5)
_cell_formula_units_Z            8
_cell_length_a                   19.569(5)
_cell_length_b                   7.808(5)
_cell_length_c                   24.645(5)
_cell_measurement_reflns_used    3126
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.1007
_cell_measurement_theta_min      3.3042
_cell_volume                     3751(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0938
_diffrn_measured_fraction_theta_full 0.848
_diffrn_measured_fraction_theta_max 0.848
_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  0.0272
_diffrn_reflns_av_sigmaI/netI    0.0530
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            17540
_diffrn_reflns_theta_full        29.17
_diffrn_reflns_theta_max         29.17
_diffrn_reflns_theta_min         3.31
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         18243
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.974
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1568
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.911
_refine_diff_density_min         -0.761
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       0.0054(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     486
_refine_ls_number_reflns         8594
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.1331
_refine_ls_R_factor_gt           0.0816
_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^)+(0.0929P)^2^+3.2620P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2041
_refine_ls_wR_factor_ref         0.2416
_reflns_number_gt                5083
_reflns_number_total             8594
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo7b02147_si_002.cif
_cod_data_source_block           shelxl_compound_7i
_cod_depositor_comments
;
Adding full bibliography for 4033002--4033004.cif.

2020-04-04
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_original_formula_sum        'C46 H42 N6 O4'
_cod_original_formula_units_Z    4
_cod_original_formula_weight     742.86
_cod_database_code               4033003