Nickel-catalyzed regio- and enantio-selective Markovnikov hydromonofluoroalkylation of 1,3-dienes
Liao, Ling; Zhang, Ying; Wu, Zhong-Wei; Ye, Zhong-Tian; Zhang, Xue-Xin; Chen, Guangying; Yu, Jin-Sheng; Chemical Science 13 (2022) 12519–12526; doi:10.1039/D2SC03958C

data_1567757
_publ_section_title
;
 Nickel-catalyzed regio- and enantio-selective Markovnikov
 hydromonofluoroalkylation of 1,3-dienes
;
_journal_issue                   42
_journal_name_full               'Chemical Science'
_journal_page_first              12519
_journal_page_last               12526
_journal_paper_doi               10.1039/D2SC03958C
_journal_volume                  13
_journal_year                    2022
_chemical_formula_sum            'C21 H23 F O4'
_chemical_formula_weight         358.39
_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-2017/1
_audit_update_record
;
2021-12-20 deposited with the CCDC.	2022-09-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.051(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.0920(2)
_cell_length_b                   5.94840(10)
_cell_length_c                   19.5057(4)
_cell_measurement_temperature    293(2)
_cell_volume                     929.64(3)
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0550
_diffrn_reflns_av_unetI/netI     0.0357
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            18308
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.052
_diffrn_reflns_theta_max         67.052
_diffrn_reflns_theta_min         4.579
_exptl_absorpt_coefficient_mu    0.778
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_F_000             380
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.160
_refine_diff_density_max         0.142
_refine_diff_density_min         -0.123
_refine_diff_density_rms         0.027
_refine_ls_abs_structure_details
;
 Flack x determined using 1319 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(9)
_refine_ls_extinction_coef       0.0031(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         3278
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0312
_refine_ls_R_factor_gt           0.0289
_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^)+(0.0388P)^2^+0.0412P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0721
_refine_ls_wR_factor_ref         0.0733
_reflns_Friedel_coverage         0.803
_reflns_Friedel_fraction_full    0.991
_reflns_Friedel_fraction_max     0.991
_reflns_number_gt                3105
_reflns_number_total             3278
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc03958c2.cif
_cod_data_source_block           exp_2326
_cod_depositor_comments
'Adding full bibliography for 1567757--1567758.cif.'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1567757
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_min   0.789
_shelx_estimated_absorpt_t_max   0.886
_shelx_res_checksum              38968
_shelx_hkl_checksum              18349