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_4518854
_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_sum            'C17 H15 F3 O'
_chemical_formula_weight         292.29
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2020-12-09 deposited with the CCDC.	2021-06-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.419(12)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.2006(11)
_cell_length_b                   6.3392(12)
_cell_length_c                   12.6940(18)
_cell_measurement_reflns_used    725
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      22.4600
_cell_measurement_theta_min      3.7420
_cell_volume                     738.2(2)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.835
_diffrn_measurement_device_type  'Oxford Diffraction Gemini R Ultra'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0166
_diffrn_reflns_av_unetI/netI     0.0381
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.835
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            3420
_diffrn_reflns_point_group_measured_fraction_full 0.805
_diffrn_reflns_point_group_measured_fraction_max 0.641
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.382
_diffrn_reflns_theta_min         3.595
_exptl_absorpt_coefficient_mu    0.106
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_description       block
_exptl_crystal_F_000             304
_refine_diff_density_max         0.105
_refine_diff_density_min         -0.124
_refine_diff_density_rms         0.028
_refine_ls_abs_structure_details
;
 Flack x determined using 452 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.3(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2624
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0779
_refine_ls_R_factor_gt           0.0424
_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^)+(0.0364P)^2^+0.0280P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0818
_refine_ls_wR_factor_ref         0.1018
_reflns_Friedel_coverage         0.415
_reflns_Friedel_fraction_full    0.576
_reflns_Friedel_fraction_max     0.411
_reflns_number_gt                1679
_reflns_number_total             2624
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs1c01483_si_001.cif
_cod_data_source_block           shelx
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4518854
_shelx_shelxl_version_number     2018/3
_shelx_res_checksum              35111
_shelx_hkl_checksum              30884