Synthesis of 2-fluorinated pyrazolo[1,5-a]pyridines via base- mediated [3+2] cycloaddition of N-aminopyridinium salts with gem-difluorostyrenes
Feng, Yang; Wu, Yuanyuan; Yue, Zengjiang; Fu, Ying; Du, Zhengyin; New Journal of Chemistry 48 (2024) 12496–12500; doi:10.1039/D4NJ02150A

data_7063289
_publ_section_title
;
 Synthesis of 2-fluorinated pyrazolo[1,5-a]pyridines via base- mediated
 [3+2] cycloaddition of N-aminopyridinium salts with gem-difluorostyrenes
;
_journal_issue                   28
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              12496
_journal_page_last               12500
_journal_paper_doi               10.1039/D4NJ02150A
_journal_volume                  48
_journal_year                    2024
_chemical_formula_moiety         'C20 H12 F N3'
_chemical_formula_sum            'C20 H12 F N3'
_chemical_formula_weight         313.33
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-09-17
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2023-10-12 deposited with the CCDC.	2024-06-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 118.0230(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   27.7164(13)
_cell_length_b                   7.2580(3)
_cell_length_c                   17.6388(7)
_cell_measurement_reflns_used    7649
_cell_measurement_temperature    298.06
_cell_measurement_theta_max      24.05
_cell_measurement_theta_min      2.93
_cell_volume                     3132.3(2)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      298.06
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0468
_diffrn_reflns_av_unetI/netI     0.0316
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            31494
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.291
_diffrn_reflns_theta_min         3.122
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.7105
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0563 before and 0.0476 after correction.
The Ratio of minimum to maximum transmission is 0.9528.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_description       block
_exptl_crystal_F_000             1296
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.146
_refine_diff_density_min         -0.124
_refine_diff_density_rms         0.029
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3890
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0878
_refine_ls_R_factor_gt           0.0459
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0458P)^2^+1.0127P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0965
_refine_ls_wR_factor_ref         0.1171
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2411
_reflns_number_total             3890
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4nj02150a2.cif
_cod_data_source_block           1
_cod_depositor_comments          'Adding full bibliography for 7063289.cif.'
_cod_database_code               7063289
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.994
_shelx_estimated_absorpt_t_min   0.986
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C10(H10), C14(H14), C16(H16), C18(H18), C20(H20), C21(H21), C15(H15),
 C2(H2), C17(H17), C9(H9), C5(H5)
;
_shelx_res_checksum              26703
_olex2_submission_special_instructions 'No special instructions were received'