Formal (4+2) cycloaddition of azoalkenes with trifluoromethylimidoyl sulfoxonium ylides: synthesis of trifluoromethyl pyridazine derivatives
Wang, Jie; Wang, Shan-Shan; Xiao, Jun; He, Yu-Jie; Wu, Xin-Yan; Li, Xingguang; Liu, Pei-Nian; Chemical Communications  (2023) –; doi:10.1039/D3CC03950A

data_7132156
_publ_section_title
;
 Formal (4+2) cycloaddition of azoalkenes with trifluoromethylimidoyl
 sulfoxonium ylides: synthesis of trifluoromethyl pyridazine derivatives
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D3CC03950A
_journal_year                    2023
_chemical_formula_sum            'C17 H17 F3 N4 O6'
_chemical_formula_weight         430.35
_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   geom
_audit_block_doi                 10.5517/ccdc.csd.cc2g8b36
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2023-06-24 deposited with the CCDC.	2023-09-25 downloaded from the CCDC.
;
_cell_angle_alpha                95.562(3)
_cell_angle_beta                 100.951(3)
_cell_angle_gamma                93.877(3)
_cell_formula_units_Z            2
_cell_length_a                   9.0815(8)
_cell_length_b                   9.9989(9)
_cell_length_c                   11.2070(10)
_cell_measurement_reflns_used    5671
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      50.831
_cell_measurement_theta_min      4.586
_cell_volume                     990.56(15)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0811
_diffrn_reflns_av_unetI/netI     0.0604
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            17758
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.993
_diffrn_reflns_theta_min         2.653
_exptl_absorpt_coefficient_mu    0.128
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5477
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.443
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             444
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.365
_refine_diff_density_min         -0.315
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       0.051(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     275
_refine_ls_number_reflns         3884
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0989
_refine_ls_R_factor_gt           0.0561
_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^)+(0.0552P)^2^+0.4080P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1288
_refine_ls_wR_factor_ref         0.1546
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2508
_reflns_number_total             3884
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc03950a2.cif
_cod_data_source_block           mo_d8v23224_0m
_cod_original_cell_volume        990.55(15)
_cod_database_code               7132156
_shelx_estimated_absorpt_t_min   0.975
_shelx_estimated_absorpt_t_max   0.992
_shelxl_version_number           2013-4
_shelx_res_checksum              95367
_shelx_hkl_checksum              45542