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_7156037
_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         'C14 H10 Cl N3 O3, C2 H6 O S'
_chemical_formula_sum            'C16 H16 Cl N3 O4 S'
_chemical_formula_weight         381.83
_chemical_name_systematic
6-Chloro-7-(2-hydroxy-5-methylphenyl)pyrido[2,3-<i>d</i>]pyrimidine-2,4(1<i>H</i>,3<i>H</i>)-dione
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -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.
;
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_cell_angle_gamma                76.9220(10)
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_cell_length_c                   15.5616(3)
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_cell_measurement_theta_min      2.73
_cell_volume                     845.17(4)
_computing_cell_refinement       'Bruker Apex V7.51A'
_computing_data_collection       'Bruker Apex V7.51A'
_computing_data_reduction        'Bruker SAINT'
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_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
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_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.990
_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
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_diffrn_reflns_av_unetI/netI     0.0302
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            27106
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.500
_diffrn_reflns_theta_min         2.674
_exptl_absorpt_coefficient_mu    0.377
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_exptl_absorpt_correction_T_min  0.6974
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.500
_exptl_crystal_description       block
_exptl_crystal_F_000             396
_exptl_crystal_size_max          0.290
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.531
_refine_diff_density_min         -0.351
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     241
_refine_ls_number_reflns         6050
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0550
_refine_ls_R_factor_gt           0.0390
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0489P)^2^+0.3361P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0941
_refine_ls_wR_factor_ref         0.1038
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4834
_reflns_number_total             6050
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ob02729j2.cif
_cod_data_source_block           is_mm258
_cod_depositor_comments
'Adding full bibliography for 7156036--7156039.cif.'
_cod_database_code               7156037
_shelx_estimated_absorpt_t_min   0.899
_shelx_estimated_absorpt_t_max   0.978
_shelxl_version_number           2013-4
_shelx_res_checksum              53544