A protocol for directly accessing geminal C-4 diarylated pyrazol-5(4<i>H</i>)-ones <i>via</i> tandem C-H aryne insertion and their inceptive neurobiological evaluation.
Sudarshana, K. A.; Sarma, Manas Jyoti; Radhakrishnan, Mydhili; Chakravarty, Sumana; Srihari, Pabbaraja; Mehta, Goverdhan; Organic & biomolecular chemistry 22 (2024) 714–719; doi:10.1039/d3ob01932b

data_7159725
_publ_section_title
;
 A protocol for directly accessing geminal C-4 diarylated
 pyrazol-5(4<i>H</i>)-ones <i>via</i> tandem C-H aryne insertion and their
 inceptive neurobiological evaluation.
;
_journal_issue                   4
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              714
_journal_page_last               719
_journal_paper_doi               10.1039/d3ob01932b
_journal_volume                  22
_journal_year                    2024
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C16 H11 F3 N2 O'
_chemical_formula_sum            'C16 H11 F3 N2 O'
_chemical_formula_weight         304.27
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2022-05-30 deposited with the CCDC.	2023-12-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.0124(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.2516(2)
_cell_length_b                   12.1242(4)
_cell_length_c                   19.5002(7)
_cell_measurement_reflns_used    7697
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      23.03
_cell_measurement_theta_min      2.68
_cell_volume                     1477.80(9)
_computing_cell_refinement       '<i>SAINT</i> (Bruker, 2016)'
_computing_data_collection       '<i>APEX3</i> (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  '<i>SHELXL2014</i> (Sheldrick, 2015)'
_computing_structure_solution    '<i>SHELXT</i> (Sheldrick, 2015)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.913
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-100'
_diffrn_measurement_method       '\w and \f'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0994
_diffrn_reflns_av_unetI/netI     0.1080
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.913
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            33792
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.863
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.765
_diffrn_reflns_theta_min         2.681
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.5192
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Bruker, 2016'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.368
_exptl_crystal_description       block
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.259
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.087
_refine_ls_abs_structure_details
;
 Flack x determined using 1175 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(5)
_refine_ls_extinction_coef       0.024(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     453
_refine_ls_number_reflns         7270
_refine_ls_number_restraints     184
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.1941
_refine_ls_R_factor_gt           0.0743
_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^)+(0.0467P)^2^+0.2256P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1227
_refine_ls_wR_factor_ref         0.1574
_reflns_Friedel_coverage         0.810
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.808
_reflns_number_gt                3290
_reflns_number_total             7270
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob01932b2.cif
_cod_data_source_block           KA1013_0m
_cod_depositor_comments
'Adding full bibliography for 7159724--7159726.cif.'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7159725
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.971
_shelx_estimated_absorpt_t_max   0.983
_shelx_res_checksum              76927