2,3-unsubstituted chromones and their enaminone precursors as versatile reagents for the synthesis of fused pyridines.
Iaroshenko, Viktor O.; Mkrtchyan, Satenik; Gevorgyan, Ashot; Miliutina, Mariia; Villinger, Alexander; Volochnyuk, Dmytro; Sosnovskikh, Vyacheslav Ya; Langer, Peter; Organic & biomolecular chemistry 10 (2012) 890–894; doi:10.1039/c1ob06494k

data_7152146
_publ_section_title
;
 2,3-unsubstituted chromones and their enaminone precursors as versatile
 reagents for the synthesis of fused pyridines.
;
_journal_issue                   4
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              890
_journal_page_last               894
_journal_paper_doi               10.1039/c1ob06494k
_journal_volume                  10
_journal_year                    2012
_chemical_formula_moiety         'C18 H12 Cl N3 O2'
_chemical_formula_sum            'C18 H12 Cl N3 O2'
_chemical_formula_weight         337.76
_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                90.00
_cell_angle_beta                 110.969(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.5897(4)
_cell_length_b                   11.4742(3)
_cell_length_c                   10.2062(3)
_cell_measurement_reflns_used    6354
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      64.675
_cell_measurement_theta_min      5.557
_cell_volume                     1486.07(8)
_computing_cell_refinement       'Bruker Apex v2.0-2'
_computing_data_collection       'Bruker Apex v2.0-2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker-Nonius Apex X8-CCD-diffractometer'
_diffrn_measurement_method       'phi and psi scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0238
_diffrn_reflns_av_sigmaI/netI    0.0230
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            17175
_diffrn_reflns_theta_full        29.00
_diffrn_reflns_theta_max         29.00
_diffrn_reflns_theta_min         2.78
_exptl_absorpt_coefficient_mu    0.274
_exptl_absorpt_correction_T_max  0.9627
_exptl_absorpt_correction_T_min  0.9151
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.510
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.325
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     225
_refine_ls_number_reflns         3944
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0454
_refine_ls_R_factor_gt           0.0347
_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^)+(0.0528P)^2^+0.2511P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0923
_refine_ls_wR_factor_ref         0.0971
_reflns_number_gt                3251
_reflns_number_total             3944
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            c1ob06494k.txt
_cod_data_source_block           is_ag124
_cod_original_cell_volume        1486.07(7)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7152146