Base-mediated [3 + 2]-cycloannulation strategy for the synthesis of pyrazolo[1,5-a]pyridine derivatives using (E)-β-iodovinyl sulfones
Jannapu Reddy, Raju; Sharadha, Nunavath; Haritha Kumari, Arram; Organic & Biomolecular Chemistry  (2022) –; doi:10.1039/D2OB00499B

data_7158647
_publ_section_title
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 Base-mediated [3 + 2]-cycloannulation strategy for the synthesis of
 pyrazolo[1,5-a]pyridine derivatives using (E)-\b-iodovinyl sulfones
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_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB00499B
_journal_year                    2022
_chemical_formula_moiety         'C20 H16 N2 O2 S'
_chemical_formula_sum            'C20 H16 N2 O2 S'
_chemical_formula_weight         348.41
_chemical_melting_point          134(2)
_chemical_name_common            3-sulfonyl-pyrazolo[1,5-a]pyridines
_chemical_name_systematic        2-Phenyl-3-tosylpyrazolo[1,5-a]pyridine
_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'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2022-03-14 deposited with the CCDC.	2022-04-13 downloaded from the CCDC.
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_cell_angle_alpha                90
_cell_angle_beta                 99.534(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.6434(13)
_cell_length_b                   12.8669(18)
_cell_length_c                   15.514(3)
_cell_measurement_reflns_used    9585
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.52
_cell_measurement_theta_min      2.99
_cell_volume                     1701.5(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.955
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON II CPAD'
_diffrn_measurement_method       '\ f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0377
_diffrn_reflns_av_unetI/netI     0.0138
_diffrn_reflns_Laue_measured_fraction_full 0.955
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            61862
_diffrn_reflns_point_group_measured_fraction_full 0.955
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.000
_diffrn_reflns_theta_min         2.068
_exptl_absorpt_coefficient_mu    0.206
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS; Bruker, 2016'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.360
_exptl_crystal_description       Plate
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.453
_refine_diff_density_min         -0.408
_refine_diff_density_rms         0.097
_refine_ls_extinction_coef       0.253(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.164
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3563
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.164
_refine_ls_R_factor_all          0.0368
_refine_ls_R_factor_gt           0.0344
_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^)+(0.0599P)^2^+0.7013P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0966
_refine_ls_wR_factor_ref         0.1105
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3520
_reflns_number_total             3563
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob00499b2.cif
_cod_data_source_block           4a
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7158647
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              56796
_publcif_funding_html
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