Ligand-free palladium catalyzed facile construction of tetra cyclic dibenzo[b,h][1,6]naphthyridine derivatives: Domino sequence of intramolecular C-H bond arylation and oxidation reactions
singh, jay bahadur; Bharadwaj, Kishor Chandra; Gupta, Tanu; Singh, Radhey M.; RSC Adv.  (2016) –; doi:10.1039/C6RA00505E

data_7224526
_publ_section_title
;
 Ligand-free palladium catalyzed facile construction of tetra cyclic
 dibenzo[b,h][1,6]naphthyridine derivatives: Domino sequence of
 intramolecular C-H bond arylation and oxidation reactions
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C6RA00505E
_journal_year                    2016
_chemical_formula_sum            'C16 H9 F N2'
_chemical_formula_weight         248.25
_chemical_melting_point          438.0(10)
_chemical_name_systematic        '2-Fluoro-dibenzo[b,h][1,6]naphthyridine '
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_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
_audit_update_record
;
2016-01-01 deposited with the CCDC.
2016-03-02 downloaded from the CCDC.
;
_cell_angle_alpha                77.609(5)
_cell_angle_beta                 78.327(5)
_cell_angle_gamma                75.424(5)
_cell_formula_units_Z            4
_cell_length_a                   10.153(5)
_cell_length_b                   10.171(5)
_cell_length_c                   12.242(5)
_cell_measurement_reflns_used    1104
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.0794
_cell_measurement_theta_min      3.0885
_cell_volume                     1180.2(10)
_computing_cell_refinement       'Crysalis, Oxford Diffraction'
_computing_data_collection       'Crysalis, Oxford Diffraction'
_computing_data_reduction        'Crysalis, Oxford Diffraction'
_computing_molecular_graphics    PLATON(Spek,2004)
_computing_publication_material  'SHELXL, PLATON, WINGX (Ferrugia, 2012)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXL (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.98
_diffrn_measured_fraction_theta_max 0.683
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'CrysAlisPro, Agilent Technologies'
_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  0.0132
_diffrn_reflns_av_sigmaI/netI    0.0422
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5540
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         29.12
_diffrn_reflns_theta_min         3.45
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91791
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlisPro, Agilent Technologies'
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       cubic
_exptl_crystal_F_000             512.0
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: CHCl3'
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.146
_refine_diff_density_min         -0.154
_refine_diff_density_rms         0.031
_refine_ls_extinction_coef       0.0063(12)
_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   1.024
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     344
_refine_ls_number_reflns         4321
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0842
_refine_ls_R_factor_gt           0.0480
_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^)+(0.0475P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1035
_refine_ls_wR_factor_ref         0.1297
_reflns_number_gt                2649
_reflns_number_total             4321
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            c6ra00505e2.cif
_cod_data_source_block           jb-uq6-fah
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '437-439' was changed to '438.0(10)'
- the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 
;
_cod_original_sg_symbol_H-M      P-1
_cod_original_formula_sum        ' C16 H9 F N2'
_cod_database_code               7224526