Synthesis of naphthyridin-2(1H)-one derivatives via ring expansion of 3-substituted-1H-pyrrolo[2,3-b]pyridin-2(3H)-one derivatives.
Croix, C.; Massip, S.; Viaud-Massuard, M-C; Chemical communications (Cambridge, England) 54 (2018) 5538–5541; doi:10.1039/c8cc01518j

data_7121593
_publ_section_title
;
 Synthesis of naphthyridin-2(1H)-one derivatives via ring expansion of
 3-substituted-1H-pyrrolo[2,3-b]pyridin-2(3H)-one derivatives.
;
_journal_issue                   44
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              5538
_journal_page_last               5541
_journal_paper_doi               10.1039/c8cc01518j
_journal_volume                  54
_journal_year                    2018
_chemical_formula_sum            'C61.5 H53.5 Cl4.5 N12 O4'
_chemical_formula_weight         1184.19
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_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
;
2017-01-19 deposited with the CCDC.
2018-05-01 downloaded from the CCDC.
;
_cell_angle_alpha                74.323(5)
_cell_angle_beta                 82.323(6)
_cell_angle_gamma                77.013(5)
_cell_formula_units_Z            2
_cell_length_a                   10.82470(10)
_cell_length_b                   14.6849(2)
_cell_length_c                   19.4686(13)
_cell_measurement_reflns_used    9025
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      68.25
_cell_measurement_theta_min      2.36
_cell_volume                     2894.6(2)
_computing_cell_refinement       'CrystalClear Expert 2.1 43b(Rigaku, 2013)'
_computing_data_collection       'CrystalClear Expert 2.1 43b(Rigaku, 2013)'
_computing_data_reduction        'CrystalClear Expert 2.1 43b(Rigaku, 2013)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Rigaku RAXIS Rapid'
_diffrn_measurement_method       \w-scans
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_source         'micro-focus rotating anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0324
_diffrn_reflns_av_sigmaI/netI    0.0258
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            44251
_diffrn_reflns_theta_full        68.25
_diffrn_reflns_theta_max         68.25
_diffrn_reflns_theta_min         2.36
_exptl_absorpt_coefficient_mu    2.552
_exptl_absorpt_correction_T_max  0.8830
_exptl_absorpt_correction_T_min  0.7008
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear Expert 2.1 43b(Rigaku, 2013)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1230
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_platon_squeeze_details
;
The unit cell contains 1 disordered molecule of chloroform around the inversion 
center  and which have been treated as a diffuse contribution to the overall 
scatering without specific atom positions by SQUEEZE/PLATON.
;
_refine_diff_density_max         1.146
_refine_diff_density_min         -0.854
_refine_diff_density_rms         0.071
_refine_ls_extinction_coef       0.00164(18)
_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   1.026
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     750
_refine_ls_number_reflns         10437
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0609
_refine_ls_R_factor_gt           0.0546
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0984P)^2^+2.2180P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1556
_refine_ls_wR_factor_ref         0.1704
_reflns_number_gt                9025
_reflns_number_total             10437
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c8cc01518j2.cif
_cod_data_source_block           ccx481t2
_cod_depositor_comments
'Adding full bibliography for 7121592--7121593.cif.'
_cod_original_sg_symbol_H-M      P-1
_cod_original_formula_sum        'C61.50 H53.50 Cl4.50 N12 O4'
_cod_database_code               7121593