A regioselective synthesis of 3,4-diaryl-1<i>H</i>-pyrazoles through a 1,3-dipolar cycloaddition of tosylhydrazones and nitroalkenes.
García-Mejía, Carlos D; Hernández-Vázquez, Eduardo; Alejandro Ibarra-Hernández, Javier; Tarbuck-Valle, Atl; Ramírez-Apán, María T; Organic & biomolecular chemistry 21 (2023) 6205–6217; doi:10.1039/d3ob00753g

data_7159519
_publ_section_title
;
 A regioselective synthesis of 3,4-diaryl-1<i>H</i>-pyrazoles through a
 1,3-dipolar cycloaddition of tosylhydrazones and nitroalkenes.
;
_journal_issue                   30
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6205
_journal_page_last               6217
_journal_paper_doi               10.1039/d3ob00753g
_journal_volume                  21
_journal_year                    2023
_chemical_formula_sum            'C15 H12 Cl N3'
_chemical_formula_weight         269.73
_chemical_name_systematic
3-(4-(4-chlorophenyl)-5-methyl-1H-pyrazol-3-yl)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   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2019/1
_audit_update_record
;
2023-06-02 deposited with the CCDC.	2023-07-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.5870(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.1324(5)
_cell_length_b                   8.3919(3)
_cell_length_c                   11.1269(4)
_cell_measurement_reflns_used    9903
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.95
_cell_measurement_theta_min      2.84
_cell_volume                     1282.69(8)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics
; 
Ortep-3 Ver 2.02 L.J. Farrugia (1997) J. Appl. Cryst. 30, 565 
;
_computing_publication_material  'SHELXTL  (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0187
_diffrn_reflns_av_unetI/netI     0.0110
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            18891
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.948
_diffrn_reflns_theta_min         2.844
_diffrn_source                   'Incoatec ImuS'
_exptl_absorpt_coefficient_mu    0.286
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7186
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D., 
 J. Appl. Cryst. 48 (2015) 3-10 
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_description       prism
_exptl_crystal_F_000             560
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Acetone'
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.261
_exptl_crystal_size_min          0.208
_refine_diff_density_max         0.407
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         3087
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0323
_refine_ls_R_factor_gt           0.0304
_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^)+(0.0441P)^2^+0.6530P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0845
_refine_ls_wR_factor_ref         0.0861
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2890
_reflns_number_total             3087
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob00753g2.cif
_cod_data_source_block           089HVE23
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7159519
_shelx_shelxl_version_number     2019/1
_shelx_estimated_absorpt_t_min   0.904
_shelx_estimated_absorpt_t_max   0.943
_exptl_absorpt_special_details
;
 The following wavelength and cell were deduced by SADABS from the
 direction cosines etc. They are given here for emergency use only:
 CELL 0.71077   11.146    8.404   14.156   90.008  103.603   90.012
;
_shelx_res_checksum              10387