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_1570174
_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            'C13 H15 F O2'
_chemical_formula_weight         222.25
_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   mixed
_audit_creation_method           SHELXL-2017/1
_audit_update_record
;
2023-06-26 deposited with the CCDC.	2023-10-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.606(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.7657(2)
_cell_length_b                   8.4827(4)
_cell_length_c                   12.1582(5)
_cell_measurement_temperature    571(2)
_cell_volume                     586.30(4)
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      571(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  0.0642
_diffrn_reflns_av_unetI/netI     0.0404
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10142
_diffrn_reflns_point_group_measured_fraction_full 0.948
_diffrn_reflns_point_group_measured_fraction_max 0.948
_diffrn_reflns_theta_full        67.066
_diffrn_reflns_theta_max         67.066
_diffrn_reflns_theta_min         3.687
_exptl_absorpt_coefficient_mu    0.779
_exptl_crystal_density_diffrn    1.259
_exptl_crystal_F_000             236
_exptl_crystal_size_max          0.330
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.220
_refine_diff_density_max         0.114
_refine_diff_density_min         -0.129
_refine_diff_density_rms         0.027
_refine_ls_abs_structure_details
;
 Flack x determined using 716 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.128
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         1977
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.128
_refine_ls_R_factor_all          0.0419
_refine_ls_R_factor_gt           0.0387
_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^)+(0.0527P)^2^+0.0372P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1043
_refine_ls_wR_factor_ref         0.1069
_reflns_Friedel_coverage         0.773
_reflns_Friedel_fraction_full    0.892
_reflns_Friedel_fraction_max     0.892
_reflns_number_gt                1796
_reflns_number_total             1977
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc04474b2.cif
_cod_data_source_block           exp_2845
_cod_depositor_comments
'Adding full bibliography for 1570174--1570176.cif.'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1570174
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_min   0.783
_shelx_estimated_absorpt_t_max   0.847
_shelx_res_checksum              53817