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_7133793
_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         'H2 O, 2(C10 H5 F3 N4)'
_chemical_formula_sum            'C20 H12 F6 N8 O'
_chemical_formula_weight         494.38
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_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                95.204(3)
_cell_angle_beta                 93.854(3)
_cell_angle_gamma                90.608(4)
_cell_formula_units_Z            2
_cell_length_a                   7.5837(6)
_cell_length_b                   8.1452(7)
_cell_length_c                   16.1468(13)
_cell_measurement_reflns_used    6112
_cell_measurement_temperature    170.00
_cell_measurement_theta_max      60.700
_cell_measurement_theta_min      4.744
_cell_volume                     990.90(14)
_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 0.981
_diffrn_measured_fraction_theta_max 0.980
_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  0.0493
_diffrn_reflns_av_unetI/netI     0.0603
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            13566
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         56.962
_diffrn_reflns_theta_min         4.743
_diffrn_source_current           3.57
_diffrn_source_power             0.24954300000000001
_diffrn_source_voltage           69.9
_exptl_absorpt_coefficient_mu    0.833
_exptl_absorpt_correction_T_max  0.7519
_exptl_absorpt_correction_T_min  0.6405
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0968 before and 0.0598 after correction.
The Ratio of minimum to maximum transmission is 0.8518.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.657
_exptl_crystal_description       plate
_exptl_crystal_F_000             500
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.264
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     319
_refine_ls_number_reflns         3971
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0484
_refine_ls_R_factor_gt           0.0400
_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^)+(0.0510P)^2^+0.1139P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1005
_refine_ls_wR_factor_ref         0.1049
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3267
_reflns_number_total             3971
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc03826f2.cif
_cod_data_source_block           240707_mlq_2_93_0m
_cod_depositor_comments
'Adding full bibliography for 7133792--7133794.cif.'
_cod_database_code               7133793
_shelx_shelxl_version_number     2019/2
_shelx_estimated_absorpt_t_max   0.975
_shelx_estimated_absorpt_t_min   0.892
_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 O(H,H) groups
2.a Free rotating group:
 O1(H1A,H1B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), N4(H4), C5(H5), C6(H6), N8(H8), C11(H11), C12(H12), C15(H15),
 C16(H16)
;
_olex2_submission_special_instructions 'No special instructions were received'