Nickel-catalysed asymmetric hydromonofluoromethylation of 1,3-enynes for enantioselective construction of monofluoromethyl-tethered chiral allenes.
Zhang, Ying; Yang, Jimin; Ruan, Yu-Long; Liao, Ling; Ma, Chuang; Xue, Xiao-Song; Yu, Jin-Sheng; Chemical science 14 (2023) 12676–12683; doi:10.1039/d3sc04474b

data_1570175
_publ_section_title
;
 Nickel-catalysed asymmetric hydromonofluoromethylation of 1,3-enynes for
 enantioselective construction of monofluoromethyl-tethered chiral
 allenes.
;
_journal_issue                   44
_journal_name_full               'Chemical science'
_journal_page_first              12676
_journal_page_last               12683
_journal_paper_doi               10.1039/d3sc04474b
_journal_volume                  14
_journal_year                    2023
_chemical_formula_sum            'C21 H17 F O4 S3'
_chemical_formula_weight         448.52
_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-2018/3
_audit_update_record
;
2023-06-26 deposited with the CCDC.	2023-10-23 downloaded from the CCDC.
;
_cell_angle_alpha                103.159(2)
_cell_angle_beta                 96.871(2)
_cell_angle_gamma                116.633(3)
_cell_formula_units_Z            2
_cell_length_a                   9.6128(3)
_cell_length_b                   10.2795(3)
_cell_length_c                   12.5045(3)
_cell_measurement_temperature    298(2)
_cell_volume                     1040.05(6)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0751
_diffrn_reflns_av_unetI/netI     0.0557
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_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       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            23484
_diffrn_reflns_point_group_measured_fraction_full 0.924
_diffrn_reflns_point_group_measured_fraction_max 0.924
_diffrn_reflns_theta_full        67.075
_diffrn_reflns_theta_max         67.075
_diffrn_reflns_theta_min         3.754
_exptl_absorpt_coefficient_mu    3.562
_exptl_crystal_density_diffrn    1.432
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.390
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.260
_refine_diff_density_max         0.404
_refine_diff_density_min         -0.453
_refine_diff_density_rms         0.059
_refine_ls_abs_structure_details
;
 Flack x determined using 2587 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.060(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     523
_refine_ls_number_reflns         6878
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0555
_refine_ls_R_factor_gt           0.0531
_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^)+(0.1087P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1505
_refine_ls_wR_factor_ref         0.1541
_reflns_Friedel_coverage         0.856
_reflns_Friedel_fraction_full    0.853
_reflns_Friedel_fraction_max     0.853
_reflns_number_gt                6319
_reflns_number_total             6878
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc04474b2.cif
_cod_data_source_block           exp_3357
_cod_depositor_comments
;
Adding full bibliography for 1570174--1570176.cif.

2025-05-14
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C42 H34 F2 O8 S6'
_cod_original_formula_weight         897.05
_cod_original_formula_units_Z            1
_cod_database_code               1570175
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.337
_shelx_estimated_absorpt_t_max   0.458
_shelx_res_checksum              751