Design and synthesis of imidazo[1,2-α][1,8]naphthyridine derivatives as anti-HCV agents via direct C-H arylation.
Huang, Shengdian; Qing, Jie; Wang, Shuo; Wang, Huan; Zhang, Linqi; Tang, Yefeng; Organic & biomolecular chemistry 12 (2014) 2344–2348; doi:10.1039/c3ob42525h

data_7153676
_publ_section_title
;
 Design and synthesis of imidazo[1,2-\a][1,8]naphthyridine derivatives as
 anti-HCV agents via direct C-H arylation.
;
_journal_issue                   15
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2344
_journal_page_last               2348
_journal_paper_doi               10.1039/c3ob42525h
_journal_volume                  12
_journal_year                    2014
_chemical_formula_moiety         'C18 H9 F6 N3'
_chemical_formula_sum            'C18 H9 F6 N3'
_chemical_formula_weight         381.28
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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                90.00
_cell_angle_beta                 111.598(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.868(4)
_cell_length_b                   9.506(3)
_cell_length_c                   11.977(4)
_cell_measurement_reflns_used    1.47
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      1537
_cell_measurement_theta_min      27.48
_cell_volume                     1573.9(8)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 ver 1.1'
_computing_publication_material  'SHELX97 (Sheldrick, 2008)'
_computing_structure_refinement  'Olex2 ver 1.1'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       '\w scans at fixed \c = 45\%'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0365
_diffrn_reflns_av_sigmaI/netI    0.0304
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10544
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         2.60
_exptl_absorpt_coefficient_mu    0.148
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.6469
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.609
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.298
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.140
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         3570
_refine_ls_number_restraints     36
_refine_ls_restrained_S_all      1.159
_refine_ls_R_factor_all          0.0627
_refine_ls_R_factor_gt           0.0554
_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^)+(0.0648P)^2^+0.4939P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1412
_refine_ls_wR_factor_ref         0.1472
_reflns_number_gt                3166
_reflns_number_total             3570
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3ob42525h2.cif
_cod_data_source_block           a
_cod_original_cell_volume        1574.0(8)
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7153676