Fluoroalkyl N-Triftosylhydrazones as Easily Decomposable Diazo Surrogates for Asymmetric [2 + 1] Cycloaddition: Synthesis of Chiral Fluoroalkyl Cyclopropenes and Cyclopropanes
Zhang, Xinyu; Tian, Chunqi; Wang, Zhanjing; Sivaguru, Paramasivam; Nolan, Steven P.; Bi, Xihe; ACS Catalysis  (2021) 8527–8537; doi:10.1021/acscatal.1c01483

data_4518855
_publ_section_title
;
 Fluoroalkyl N-Triftosylhydrazones as Easily Decomposable Diazo Surrogates
 for Asymmetric [2 + 1] Cycloaddition: Synthesis of Chiral Fluoroalkyl
 Cyclopropenes and Cyclopropanes
;
_journal_name_full               'ACS Catalysis'
_journal_page_first              8527
_journal_page_last               8537
_journal_paper_doi               10.1021/acscatal.1c01483
_journal_year                    2021
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C22 H15 F3'
_chemical_formula_sum            'C22 H15 F3 N0 O0'
_chemical_formula_weight         336.34
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                95.974(7)
_cell_angle_beta                 99.576(7)
_cell_angle_gamma                94.985(7)
_cell_formula_units_Z            4
_cell_length_a                   6.3512(5)
_cell_length_b                   15.7186(13)
_cell_length_c                   17.6114(17)
_cell_measurement_reflns_used    1396
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.0160
_cell_measurement_theta_min      4.3490
_cell_volume                     1714.5(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'ShelXT (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.829
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0235
_diffrn_reflns_av_unetI/netI     0.0516
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.829
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            12826
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.829
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.279
_diffrn_reflns_theta_min         3.451
_diffrn_source                   'fine-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.097
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_description       block
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.31
_refine_diff_density_max         0.154
_refine_diff_density_min         -0.162
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   -0.7(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     902
_refine_ls_number_reflns         9934
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.005
_refine_ls_R_factor_all          0.1254
_refine_ls_R_factor_gt           0.0544
_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^)+(0.0576P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1160
_refine_ls_wR_factor_ref         0.1529
_reflns_Friedel_coverage         1.000
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.829
_reflns_number_gt                5087
_reflns_number_total             9934
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs1c01483_si_003.cif
_cod_data_source_block           shelx
_cod_database_code               4518855
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              50230
_shelx_hkl_checksum              87866