Synthesis of functionalized 2-salicyloylfurans, furo[3,2-b]chromen-9-ones and 2-benzoyl-8H-thieno[2,3-b]indoles by one-pot cyclizations of 3-halochromones with β-ketoamides and 1,3-dihydroindole-2-thiones.
Savych, Iryna; Gläsel, Tim; Villinger, Alexander; Sosnovskikh, Vyacheslav Ya; Iaroshenko, Viktor O.; Langer, Peter; Organic & biomolecular chemistry 13 (2015) 729–750; doi:10.1039/c4ob01730g

data_7154182
_publ_section_title
;
 Synthesis of functionalized 2-salicyloylfurans, furo[3,2-b]chromen-9-ones
 and 2-benzoyl-8H-thieno[2,3-b]indoles by one-pot cyclizations of
 3-halochromones with \b-ketoamides and 1,3-dihydroindole-2-thiones.
;
_journal_issue                   3
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              729
_journal_page_last               750
_journal_paper_doi               10.1039/c4ob01730g
_journal_volume                  13
_journal_year                    2015
_chemical_formula_moiety         'C20 H16 Cl N O5, C2 H6 O S'
_chemical_formula_sum            'C22 H22 Cl N O6 S'
_chemical_formula_weight         463.92
_chemical_name_systematic
'<i>N</i>-(4-Chlorophenyl)-5-[(2-hydroxy-4-methoxyphenyl)carbonyl]-2-methylfuran-3-carboxamide * dimethylsulfoxide'
_space_group_IT_number           11
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      11
_symmetry_space_group_name_Hall  '-P 2yb'
_symmetry_space_group_name_H-M   'P 1 21/m 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                 91.2010(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.7020(2)
_cell_length_b                   6.89430(10)
_cell_length_c                   16.0179(3)
_cell_measurement_reflns_used    8112
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      70.723
_cell_measurement_theta_min      4.864
_cell_volume                     1071.18(3)
_computing_cell_refinement       'Bruker Apex v7.51a'
_computing_data_collection       'Bruker Apex v7.51a'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'ORTEP-3v2.01 (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 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker-Nonius Apex X8-CCD-diffractometer'
_diffrn_measurement_method       'phi and omega 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  0.0217
_diffrn_reflns_av_sigmaI/netI    0.0189
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            18612
_diffrn_reflns_theta_full        31.99
_diffrn_reflns_theta_max         31.99
_diffrn_reflns_theta_min         2.54
_exptl_absorpt_coefficient_mu    0.316
_exptl_absorpt_correction_T_max  0.9601
_exptl_absorpt_correction_T_min  0.9168
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.438
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             484
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.470
_refine_diff_density_min         -0.374
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         3979
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0465
_refine_ls_R_factor_gt           0.0382
_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^)+(0.0640P)^2^+0.2644P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1038
_refine_ls_wR_factor_ref         0.1126
_reflns_number_gt                3373
_reflns_number_total             3979
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            c4ob01730g2.cif
_cod_data_source_block           is_is3801
_cod_depositor_comments
'Adding full bibliography for 7154181--7154183.cif.'
_cod_original_sg_symbol_H-M      'P 21/m'
_cod_database_code               7154182