An expeditious and efficient synthesis of highly functionalized [1,6]-naphthyridines under catalyst-free conditions in aqueous medium.
Mukhopadhyay, Chhanda; Das, Paramita; Butcher, Ray J.; Organic letters 13 (2011) 4664–4667; doi:10.1021/ol201877v

data_1502420
_publ_section_title
;
 An expeditious and efficient synthesis of highly functionalized
 [1,6]-naphthyridines under catalyst-free conditions in aqueous medium.
;
_journal_issue                   17
_journal_name_full               'Organic letters'
_journal_page_first              4664
_journal_page_last               4667
_journal_paper_doi               10.1021/ol201877v
_journal_volume                  13
_journal_year                    2011
_chemical_formula_moiety         'C24 H23 N5'
_chemical_formula_sum            'C24 H23 N5'
_chemical_formula_weight         381.47
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                90.00
_cell_angle_beta                 98.547(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   27.867(3)
_cell_length_b                   10.0431(8)
_cell_length_c                   14.5453(11)
_cell_measurement_reflns_used    2717
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      75.2321
_cell_measurement_theta_min      4.6824
_cell_volume                     4025.6(6)
_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_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      123(2)
_diffrn_detector_area_resol_mean 10.5081
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0264
_diffrn_reflns_av_sigmaI/netI    0.0329
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7826
_diffrn_reflns_theta_full        67.50
_diffrn_reflns_theta_max         75.41
_diffrn_reflns_theta_min         4.69
_exptl_absorpt_coefficient_mu    0.604
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83786
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.259
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       chunk
_exptl_crystal_F_000             1616
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.278
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     269
_refine_ls_number_reflns         4037
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0604
_refine_ls_R_factor_gt           0.0488
_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^)+(0.0685P)^2^+2.5961P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1328
_refine_ls_wR_factor_ref         0.1433
_reflns_number_gt                3260
_reflns_number_total             4037
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            ol201877v_si_004.cif
_cod_data_source_block           cm-27
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               1502420