Synthesis of 3,6-diaryl-1H-pyrazolo[3,4-b]pyridines via one-pot sequential Suzuki–Miyaura coupling
Urvashi, Urvashi; Tandon, Vibha; Das, Parthasarathi; Kukreti, S.; RSC Advances 8 (2018) 34883–; doi:10.1039/C8RA07104G

data_7231656
_publ_section_title
;
 Synthesis of 3,6-diaryl-1H-pyrazolo[3,4-b]pyridines via one-pot
 sequential Suzuki--Miyaura coupling
;
_journal_issue                   61
_journal_name_full               'RSC Advances'
_journal_page_first              34883
_journal_paper_doi               10.1039/C8RA07104G
_journal_volume                  8
_journal_year                    2018
_chemical_formula_moiety         'C15 H9 F6 N3'
_chemical_formula_sum            'C15 H9 F6 N3'
_chemical_formula_weight         345.25
_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   geom
_audit_creation_method           SHELXL-2016/4
_audit_update_record
;
2018-03-10 deposited with the CCDC.
2018-09-20 downloaded from the CCDC.
;
_cell_angle_alpha                87.684(7)
_cell_angle_beta                 88.220(7)
_cell_angle_gamma                75.359(8)
_cell_formula_units_Z            4
_cell_length_a                   9.9699(8)
_cell_length_b                   11.2846(10)
_cell_length_c                   13.4112(11)
_cell_measurement_reflns_used    2323
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      21.5150
_cell_measurement_theta_min      3.4860
_cell_volume                     1458.3(2)
_computing_cell_refinement       'X-calibur S SAINT'
_computing_data_collection       'X-calibur S oxford'
_computing_data_reduction        'X-calibur S SAINT'
_computing_molecular_graphics    'Oxford SHELXTL'
_computing_publication_material  'Oxford SHELXTL'
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0433
_diffrn_reflns_av_unetI/netI     0.0635
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            16198
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         3.152
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.150
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_diffrn    1.573
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.717
_refine_diff_density_min         -0.528
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     433
_refine_ls_number_reflns         5119
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.1665
_refine_ls_R_factor_gt           0.1064
_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^)+(0.1514P)^2^+1.7728P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2881
_refine_ls_wR_factor_ref         0.3417
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2783
_reflns_number_total             5119
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ra07104g2.cif
_cod_data_source_block           shelx_CCDC1
_cod_database_code               7231656
_shelx_shelxl_version_number     2016/4
_shelx_res_checksum              10732
_shelx_hkl_checksum              49254