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_7152150
_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 H19 N3 O S'
_chemical_formula_sum            'C18 H19 N3 O S'
_chemical_formula_weight         325.42
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.3395(2)
_cell_length_b                   7.8493(3)
_cell_length_c                   31.3577(12)
_cell_measurement_reflns_used    4335
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      60.852
_cell_measurement_theta_min      5.196
_cell_volume                     1560.38(10)
_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  0.0322
_diffrn_reflns_av_sigmaI/netI    0.0439
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       44
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_number            14344
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         2.90
_exptl_absorpt_coefficient_mu    0.216
_exptl_absorpt_correction_T_max  0.9936
_exptl_absorpt_correction_T_min  0.9148
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.385
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.39
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.264
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.04(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         4521
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0498
_refine_ls_R_factor_gt           0.0364
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0403P)^2^+0.0651P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0772
_refine_ls_wR_factor_ref         0.0824
_reflns_number_gt                3876
_reflns_number_total             4521
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            c1ob06494k.txt
_cod_data_source_block           is_ag188
_cod_database_code               7152150