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_1567758
_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_absolute_configuration unk
_chemical_formula_moiety         'C23 H21 F O4 S2'
_chemical_formula_sum            'C23 H21 F O4 S2'
_chemical_formula_weight         444.52
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-09-14
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-12-19 deposited with the CCDC.	2022-09-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.55430(10)
_cell_length_b                   10.05800(10)
_cell_length_c                   28.1125(2)
_cell_measurement_reflns_used    37389
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      74.2200
_cell_measurement_theta_min      4.3360
_cell_volume                     2136.02(4)
_computing_cell_refinement       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      173.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -26.00   4.00   1.00    1.00    --    0.00 -37.00 120.00   30
  2  \w    -58.00  24.00   1.00    1.00    --    0.00 -19.00 -90.00   82
  3  \w     26.00  74.00   1.00    1.00    --    0.00  37.00-180.00   48
  4  \w     41.00  87.00   1.00    1.00    --    0.00  77.00 -30.00   46
  5  \w    -33.00  32.00   1.00    1.00    --    0.00 -82.00 120.00   65
  6  \w    -41.00   2.00   1.00    1.00    --    0.00 -57.00  30.00   43
  7  \w     52.00  83.00   1.00    1.00    --    0.00  37.00 120.00   31
  8  \w    -21.00  23.00   1.00    1.00    --    0.00 -19.00 120.00   44
  9  \w    -19.00  15.00   1.00    1.00    --    0.00  37.00-180.00   34
 10  \w    -29.00  21.00   1.00    1.00    --    0.00  77.00 -30.00   50
 11  \w    -89.00 -51.00   1.00    1.00    --    0.00 -37.00 120.00   38
 12  \w    -89.00 -54.00   1.00    1.00    --    0.00 -82.00 120.00   35
 13  \w    -74.00 -44.00   1.00    1.00    --    0.00 -57.00  30.00   30
 14  \w    -12.00  50.00   1.00    1.00    --    0.00  37.00 120.00   62
 15  \w     65.00 108.00   1.00    1.00    --   95.80  77.00 -30.00   43
 16  \w     54.00 118.00   1.00    1.00    --   95.80 -82.00-180.00   64
 17  \w    126.00 184.00   1.00    1.00    --   95.80  67.00 -37.34   58
 18  \w     94.00 185.00   1.00    1.00    --   95.80  82.00  42.52   91
 19  \w     63.00  89.00   1.00    1.00    --   95.80  82.00  42.52   26
 20  \w     69.00  95.00   1.00    1.00    --   95.80  67.00 -37.34   26
 21  \w     68.00 184.00   1.00    1.00    --   95.80  68.00-144.15  116
 22  \w    150.00 185.00   1.00    1.00    --   95.80  77.00 120.00   35
 23  \w     63.00  88.00   1.00    1.00    --   95.80  82.00   0.00   25
 24  \w     71.00  97.00   1.00    1.00    --   95.80  61.00 -60.00   26
 25  \w     63.00  88.00   1.00    1.00    --   95.80  82.00-150.00   25
 26  \w     65.00 120.00   1.00    1.00    --   95.80  77.00 150.00   55
 27  \w     68.00  93.00   1.00    1.00    --   95.80  82.00 -90.00   25
 28  \w    149.00 183.00   1.00    1.00    --   95.80  82.00 -90.00   34
 29  \w      6.00 120.00   1.00    1.00    --   95.80 -61.00  30.00  114
 30  \w     65.00 169.00   1.00    1.00    --   95.80  77.00  30.00  104
 31  \w     65.00  91.00   1.00    1.00    --   95.80  77.00 120.00   26
 32  \w    133.00 180.00   1.00    1.00    --   95.80  82.00  69.13   47
 33  \w     65.00  98.00   1.00    1.00    --   95.80  77.00   0.00   33
 34  \w     63.00  97.00   1.00    1.00    --   95.80  82.00-120.00   34
 35  \w     64.00  93.00   1.00    1.00    --   95.80  82.00  69.13   29
 36  \w     74.00 135.00   1.00    1.00    --   95.80  51.00 -34.88   61
 37  \w     63.00  88.00   1.00    1.00    --   95.80  82.00 150.00   25
 38  \w     65.00  90.00   1.00    1.00    --   95.80  77.00 -60.00   25
 39  \w     65.00  90.00   1.00    1.00    --   95.80  77.00-180.00   25
 40  \w     63.00  88.00   1.00    1.00    --   95.80  82.00 -30.00   25
 41  \w    135.00 185.00   1.00    1.00    --   95.80  82.00 -30.00   50
 42  \w    149.00 174.00   1.00    1.00    --   95.80  79.00  16.47   25
 43  \w     65.00  90.00   1.00    1.00    --   95.80  77.00-120.00   25
 44  \w     75.00 149.00   1.00    1.00    --   95.80  45.00  30.00   74
 45  \w     71.00  97.00   1.00    1.00    --   95.80  61.00  60.00   26
 46  \w     65.00  91.00   1.00    1.00    --   95.80  77.00  90.00   26
 47  \w     71.00  97.00   1.00    1.00    --   95.80  61.00 150.00   26
 48  \w     63.00  88.00   1.00    1.00    --   95.80  82.00  60.00   25
 49  \w     24.00 128.00   1.00    1.00    --   95.80 -82.00 120.00  104
 50  \w     76.00 183.00   1.00    1.00    --   95.80  45.00 -60.00  107
 51  \w     71.00 154.00   1.00    1.00    --   95.80  61.00-180.00   83
 52  \w     73.00 104.00   1.00    1.00    --   95.80  61.00-150.00   31
 53  \w    135.00 169.00   1.00    1.00    --   95.80  61.00-150.00   34
 54  \w     76.00 112.00   1.00    1.00    --   95.80  45.00 150.00   36
 55  \w     65.00  99.00   1.00    1.00    --   95.80  82.00  90.00   34
 56  \w    132.00 184.00   1.00    1.00    --   95.80  82.00  90.00   52
 57  \w     10.00 109.00   1.00    1.00    --   95.80 -82.00  30.00   99
 58  \w     65.00  90.00   1.00    1.00    --   95.80  77.00 -90.00   25
 59  \w     64.00  90.00   1.00    1.00    --   95.80  79.00  16.47   26
 60  \w     73.00 184.00   1.00    1.00    --   95.80  54.00 108.82  111
 61  \w    119.00 167.00   1.00    1.00    --   95.80  49.00 -97.04   48
 62  \w     49.00 113.00   1.00    1.00    --   95.80 -82.00 -60.00   64
 63  \w     74.00 107.00   1.00    1.00    --   95.80  49.00 -97.04   33
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual offset/far'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1397479000
_diffrn_orient_matrix_UB_12      -0.1098447000
_diffrn_orient_matrix_UB_13      -0.0071500000
_diffrn_orient_matrix_UB_21      -0.0033368000
_diffrn_orient_matrix_UB_22      0.0296200000
_diffrn_orient_matrix_UB_23      -0.0537504000
_diffrn_orient_matrix_UB_31      0.1485360000
_diffrn_orient_matrix_UB_32      -0.1025487000
_diffrn_orient_matrix_UB_33      -0.0078629000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0374
_diffrn_reflns_av_unetI/netI     0.0133
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            46149
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.064
_diffrn_reflns_theta_max         67.064
_diffrn_reflns_theta_min         3.144
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.572
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69032
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.28b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.382
_exptl_crystal_description       block
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.201
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details
;
 Flack x determined using 1553 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.010(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         3742
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.097
_refine_ls_R_factor_all          0.0223
_refine_ls_R_factor_gt           0.0223
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0319P)^2^+0.4923P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0585
_refine_ls_wR_factor_ref         0.0586
_reflns_Friedel_coverage         0.725
_reflns_Friedel_fraction_full    0.991
_reflns_Friedel_fraction_max     0.991
_reflns_number_gt                3735
_reflns_number_total             3742
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc03958c2.cif
_cod_data_source_block           exp_2249
_cod_depositor_comments
'Adding full bibliography for 1567757--1567758.cif.'
_cod_database_code               1567758
_shelx_shelxl_version_number     2017/1
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C7(H7), C8(H8), C12(H12), C13(H13),
 C14(H14), C15(H15), C16(H16), C18(H18), C19(H19), C20(H20), C21(H21), C22(H22)
2.c Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C)
;
_shelx_res_checksum              49126
_shelx_hkl_checksum              31968
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.246
_oxdiff_exptl_absorpt_empirical_full_min 0.770