Scalable Sonochemical Synthetic Strategy for Pyrazolo[1,5-<i>a</i>]pyridine Derivatives: First Catalyst-Free Concerted [3 + 2] Cycloaddition of Alkyne and Alkene Derivatives to 2-Imino-1<i>H</i>-pyridin-1-amines.
Ibrahim, Hamada Mohamed; Behbehani, Haider; Mostafa, Noha S.; ACS omega 4 (2019) 7182–7193; doi:10.1021/acsomega.9b00562

data_4515056
_publ_section_title
;
 Scalable Sonochemical Synthetic Strategy for
 Pyrazolo[1,5-<i>a</i>]pyridine Derivatives: First Catalyst-Free Concerted
 [3 + 2] Cycloaddition of Alkyne and Alkene Derivatives to
 2-Imino-1<i>H</i>-pyridin-1-amines.
;
_journal_issue                   4
_journal_name_full               'ACS omega'
_journal_page_first              7182
_journal_page_last               7193
_journal_paper_doi               10.1021/acsomega.9b00562
_journal_volume                  4
_journal_year                    2019
_chemical_formula_sum            'C19 H19 N5 O5 S'
_chemical_formula_weight         429.45
_chemical_name_common            GH9_260813
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 97.338(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.135(2)
_cell_length_b                   8.1060(14)
_cell_length_c                   22.476(4)
_cell_measurement_reflns_used    8707
_cell_measurement_temperature    296.(2)
_cell_measurement_theta_max      66.5882
_cell_measurement_theta_min      3.9661
_cell_volume                     2012.1(6)
_computing_cell_refinement       'SAINT V8.18C (Bruker AXS Inc., 2011)'
_computing_data_collection       'Bruker Instrument Service v2012.4.0.0'
_computing_data_reduction        'SAINT V8.18C (Bruker AXS Inc., 2011)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'Bruker X8 Prospector'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0422
_diffrn_reflns_av_sigmaI/netI    0.0769
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            11489
_diffrn_reflns_theta_full        66.69
_diffrn_reflns_theta_max         66.69
_diffrn_reflns_theta_min         3.97
_diffrn_source_type              'Incoatec Cu-ImS'
_exptl_absorpt_coefficient_mu    1.804
_exptl_absorpt_correction_T_max  0.84
_exptl_absorpt_correction_T_min  0.64
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS Inc.)'
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_density_diffrn    1.418
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.860
_refine_diff_density_min         -0.713
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.125
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     301
_refine_ls_number_reflns         3480
_refine_ls_number_restraints     79
_refine_ls_restrained_S_all      1.161
_refine_ls_R_factor_all          0.1443
_refine_ls_R_factor_gt           0.0628
_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^)+(0.1256P)^2^+1.2867P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1888
_refine_ls_wR_factor_ref         0.2221
_reflns_number_gt                2805
_reflns_number_total             3480
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ao9b00562_si_006.cif
_cod_data_source_block           I
_cod_database_code               4515056