Synthesis of 3,5-bis(fluoroalkyl)pyrazoles/pyrazolines <i>via</i> [3 + 2] cycloaddition of di/trifluoroacetohydrazonoyl bromides and trifluoromethyl-substituted alkenes.
Wang, Ruikang; Jin, Peng; Yang, Gaowang; Fan, Ying; Bai, Zuyu; Huang, Danfeng; Wang, Ke-Hu; Wang, Junjiao; Hu, Yulai; Organic & biomolecular chemistry 23 (2025) 638–648; doi:10.1039/d4ob01160k

data_7160245
_publ_section_title
;
 Synthesis of 3,5-bis(fluoroalkyl)pyrazoles/pyrazolines <i>via</i> [3 + 2]
 cycloaddition of di/trifluoroacetohydrazonoyl bromides and
 trifluoromethyl-substituted alkenes.
;
_journal_issue                   3
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              638
_journal_page_last               648
_journal_paper_doi               10.1039/d4ob01160k
_journal_volume                  23
_journal_year                    2025
_chemical_formula_sum            'C13 H10 Br F5 N2'
_chemical_formula_weight         369.14
_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_Hall           '-P 2yac'
_space_group_name_H-M_alt        'P 1 2/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2023-12-11 deposited with the CCDC.	2024-11-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.041(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.6937(9)
_cell_length_b                   4.5126(2)
_cell_length_c                   18.7442(10)
_cell_measurement_temperature    300(2)
_cell_volume                     1445.35(13)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      300(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.936
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0543
_diffrn_reflns_av_unetI/netI     0.0641
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.936
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       2
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            8115
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.936
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.171
_diffrn_reflns_theta_min         3.061
_exptl_absorpt_coefficient_mu    4.376
_exptl_crystal_density_diffrn    1.696
_exptl_crystal_F_000             728
_refine_diff_density_max         0.623
_refine_diff_density_min         -0.598
_refine_diff_density_rms         0.085
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         2870
_refine_ls_number_restraints     24
_refine_ls_restrained_S_all      1.139
_refine_ls_R_factor_all          0.0764
_refine_ls_R_factor_gt           0.0619
_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^)+(0.1039P)^2^+0.8240P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1805
_refine_ls_wR_factor_ref         0.1962
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2170
_reflns_number_total             2870
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob01160k2.cif
_cod_data_source_block           w5-2m_1211-1_auto
_cod_depositor_comments
'Adding full bibliography for 7160245--7160246.cif.'
_cod_original_sg_symbol_H-M      'P 2/n'
_cod_database_code               7160245
_shelx_shelxl_version_number     2018/3
_shelx_res_checksum              38315