The [3+2] annulation of <i>in situ</i> formed trifluorodiazoethane with 4-nitroisoxazoles: access to trifluoromethylpyrazolo[3,4-<i>d</i>]isoxazoles.
Wang, Huamin; Meng, Li-Qin; Niu, Wenjing; Yang, Wan-Qi; Ou, Yu; Lin, Ying-Wu; Chemical communications (Cambridge, England) 60 (2024) 12425–12428; doi:10.1039/d4cc03826f

data_7133794
_publ_section_title
;
 The [3+2] annulation of <i>in situ</i> formed trifluorodiazoethane with
 4-nitroisoxazoles: access to
 trifluoromethylpyrazolo[3,4-<i>d</i>]isoxazoles.
;
_journal_issue                   85
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              12425
_journal_page_last               12428
_journal_paper_doi               10.1039/d4cc03826f
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C12 H7 Cl F3 N3 O2'
_chemical_formula_sum            'C12 H7 Cl F3 N3 O2'
_chemical_formula_weight         317.66
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-07-09
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2024-07-24 deposited with the CCDC.	2024-10-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   7.0457(6)
_cell_length_b                   23.6493(19)
_cell_length_c                   30.637(3)
_cell_measurement_reflns_used    9811
_cell_measurement_temperature    170.00
_cell_measurement_theta_max      58.583
_cell_measurement_theta_min      3.252
_cell_volume                     5104.9(8)
_computing_cell_refinement       'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_data_collection       'Bruker Instrument Service vV6.2.14'
_computing_data_reduction        'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      170.00
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0578
_diffrn_reflns_av_unetI/netI     0.0399
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            61073
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         60.679
_diffrn_reflns_theta_min         3.252
_diffrn_source_current           3.57
_diffrn_source_power             0.24957869999999996
_diffrn_source_voltage           69.91
_exptl_absorpt_coefficient_mu    2.044
_exptl_absorpt_correction_T_max  0.7519
_exptl_absorpt_correction_T_min  0.5986
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1129 before and 0.0631 after correction.
The Ratio of minimum to maximum transmission is 0.7961.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.653
_exptl_crystal_description       plate
_exptl_crystal_F_000             2560
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.274
_refine_diff_density_min         -0.365
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     381
_refine_ls_number_reflns         5844
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0582
_refine_ls_R_factor_gt           0.0417
_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^)+(0.0518P)^2^+2.6488P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1053
_refine_ls_wR_factor_ref         0.1156
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4496
_reflns_number_total             5844
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc03826f2.cif
_cod_data_source_block           240707_mlq_2_60_0m
_cod_depositor_comments
'Adding full bibliography for 7133792--7133794.cif.'
_cod_original_cell_volume        5104.9(7)
_cod_database_code               7133794
_shelx_shelxl_version_number     2019/2
_shelx_estimated_absorpt_t_max   0.941
_shelx_estimated_absorpt_t_min   0.777
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), N2(H2), C3(H3), C4(H4), N5(H5), C13(H13), C15(H15), C16(H16)
2.b Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C23(H23A,H23B,H23C)
;
_olex2_submission_special_instructions 'No special instructions were received'