A domino reaction of 3-chlorochromones with aminoheterocycles. Synthesis of pyrazolopyridines and benzofuropyridines and their optical and ecto-5'-nucleotidase inhibitory effects.
Miliutina, Mariia; Janke, Julia; Hassan, Sidra; Zaib, Sumera; Iqbal, Jamshed; Lecka, Joanna; Sévigny, Jean; Villinger, Alexander; Friedrich, Aleksej; Lochbrunner, Stefan; Langer, Peter; Organic & biomolecular chemistry 16 (2018) 717–732; doi:10.1039/c7ob02729j

data_7156039
_publ_section_title
;
 A domino reaction of 3-chlorochromones with aminoheterocycles. Synthesis
 of pyrazolopyridines and benzofuropyridines and their optical and
 ecto-5'-nucleotidase inhibitory effects.
;
_journal_issue                   5
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              717
_journal_page_last               732
_journal_paper_doi               10.1039/c7ob02729j
_journal_volume                  16
_journal_year                    2018
_chemical_formula_moiety         'C19 H14 Cl N3 O2, C2 H6 O S'
_chemical_formula_sum            'C21 H20 Cl N3 O3 S'
_chemical_formula_weight         429.91
_chemical_name_systematic
2-(5-Chloro-3-methyl-1-phenyl-1<i>H</i>-pyrazolo[3,4-<i>b</i>]pyridin-6-yl)-4-methylphenol
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2017-06-02 deposited with the CCDC.
2017-12-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.35(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
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_cell_length_c                   14.842(8)
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_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      20.87
_cell_measurement_theta_min      2.75
_cell_volume                     2074.0(19)
_computing_cell_refinement       'Bruker Apex V7.51A'
_computing_data_collection       'Bruker Apex V7.51A'
_computing_data_reduction        'Bruker SAINT'
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_computing_publication_material  SHELXL-2013
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.703
_diffrn_measured_fraction_theta_max 0.989
_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
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_diffrn_reflns_Laue_measured_fraction_full 0.703
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       21
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_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
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_diffrn_reflns_point_group_measured_fraction_full 0.703
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_diffrn_reflns_theta_max         22.362
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_exptl_absorpt_correction_T_max  0.7448
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_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'
_exptl_crystal_colour            colourless
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_exptl_crystal_description       plate
_exptl_crystal_F_000             896
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_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.010
_refine_diff_density_max         0.217
_refine_diff_density_min         -0.326
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         2637
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.1086
_refine_ls_R_factor_gt           0.0491
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0542P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0970
_refine_ls_wR_factor_ref         0.1205
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1575
_reflns_number_total             2637
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ob02729j2.cif
_cod_data_source_block           is_mm353
_cod_depositor_comments
'Adding full bibliography for 7156036--7156039.cif.'
_cod_original_cell_volume        2074(2)
_cod_database_code               7156039
_shelx_estimated_absorpt_t_min   0.864
_shelx_estimated_absorpt_t_max   0.997
_shelxl_version_number           2013-4
_shelx_res_checksum              73552