Enantioselective nickel-catalyzed <i>anti</i>-arylmetallative cyclizations onto acyclic electron-deficient alkenes.
Gillbard, Simone M.; Green, Harley; Argent, Stephen P.; Lam, Hon Wai; Chemical communications (Cambridge, England) 57 (2021) 4436–4439; doi:10.1039/d1cc01166a

data_7128131
_publ_section_title
;
 Enantioselective nickel-catalyzed <i>anti</i>-arylmetallative
 cyclizations onto acyclic electron-deficient alkenes.
;
_journal_issue                   36
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              4436
_journal_page_last               4439
_journal_paper_doi               10.1039/d1cc01166a
_journal_volume                  57
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C23 H19 F O S'
_chemical_formula_sum            'C23 H19 F O S'
_chemical_formula_weight         362.44
_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
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2020-02-19
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-10-22 deposited with the CCDC.	2021-03-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.589(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.4023(2)
_cell_length_b                   11.0606(2)
_cell_length_c                   9.9012(2)
_cell_measurement_reflns_used    6551
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      72.6920
_cell_measurement_theta_min      5.3250
_cell_volume                     907.31(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)'
_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      'N2 gas'
_diffrn_ambient_temperature      120(2)
_diffrn_crystal_treatment        'flash frozen in gaseous N2'
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 5.2349
_diffrn_detector_type            'Agilent Diffraction Atlas S2 detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.990
_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     -5.00  38.00   1.00    5.00    --  -41.70  19.00   0.00   43
  2  \w     -5.00  38.00   1.00    5.00    --  -41.70  19.00-120.00   43
  3  \w    -21.00  33.00   1.00    5.00    --  -41.70  38.00 -90.00   54
  4  \w     -5.00  38.00   1.00    5.00    --  -41.70  19.00  60.00   43
  5  \w     -5.00  38.00   1.00    5.00    --  -41.70  19.00 120.00   43
  6  \w     -5.00  38.00   1.00    5.00    --  -41.70  19.00 -30.00   43
  7  \w   -116.00 -17.00   1.00    5.00    --  -41.70 -38.00-180.00   99
  8  \w    -21.00  33.00   1.00    5.00    --  -41.70  38.00 -60.00   54
  9  \w     -5.00  38.00   1.00    5.00    --  -41.70  19.00  90.00   43
 10  \w     27.00  98.00   1.00    5.00    --   41.70-125.00  90.00   71
 11  \w     79.00 177.00   1.00   20.00    --  104.36  45.00-120.00   98
 12  \w     75.00 177.00   1.00   20.00    --  104.36  61.00-150.00  102
 13  \w     28.00  57.00   1.00   20.00    --  104.36 -30.00 -90.00   29
 14  \w     31.00  72.00   1.00   20.00    --  104.36 -45.00 150.00   41
 15  \w     75.00 177.00   1.00   20.00    --  104.36  61.00-180.00  102
 16  \w     22.00 106.00   1.00   20.00    --  104.36 -94.00 -30.00   84
 17  \w     22.00 106.00   1.00   20.00    --  104.36 -94.00  30.00   84
 18  \w     31.00  72.00   1.00   20.00    --  104.36 -45.00  30.00   41
 19  \w     76.00 178.00   1.00   20.00    --  104.36  30.00  90.00  102
 20  \w     28.00  57.00   1.00   20.00    --  104.36 -30.00 -60.00   29
 21  \w    103.00 178.00   1.00   20.00    --  104.36  77.00   0.00   75
 22  \w     76.00 178.00   1.00   20.00    --  104.36  30.00-180.00  102
 23  \w     31.00  72.00   1.00   20.00    --  104.36 -45.00 -60.00   41
 24  \w     79.00 177.00   1.00   20.00    --  104.36  45.00 -90.00   98
 25  \w     32.00  93.00   1.00   20.00    --  104.36 -61.00-120.00   61
 26  \w     32.00  93.00   1.00   20.00    --  104.36 -61.00  90.00   61
 27  \w   -114.00 -23.00   1.00    5.00    --  -41.70 -57.00 -30.00   91
;
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'SuperNova, Atlas S2'
_diffrn_measurement_method       '\w scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0531858000
_diffrn_orient_matrix_UB_12      -0.0841919000
_diffrn_orient_matrix_UB_13      -0.1232438000
_diffrn_orient_matrix_UB_21      -0.1198936000
_diffrn_orient_matrix_UB_22      -0.0630459000
_diffrn_orient_matrix_UB_23      0.0789057000
_diffrn_orient_matrix_UB_31      -0.1317328000
_diffrn_orient_matrix_UB_32      0.0913355000
_diffrn_orient_matrix_UB_33      -0.0590770000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0208
_diffrn_reflns_av_unetI/netI     0.0215
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            9932
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.796
_diffrn_reflns_theta_min         4.529
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_type              'Agilent Diffraction microfocus tube'
_exptl_absorpt_coefficient_mu    1.731
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.740
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.45a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_description       irregular
_exptl_crystal_F_000             380
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: pentane'
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.069
_exptl_crystal_size_min          0.027
_refine_diff_density_max         0.205
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details
;
 Flack x determined using 1593 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.001(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     293
_refine_ls_number_reflns         3539
_refine_ls_number_restraints     323
_refine_ls_restrained_S_all      0.984
_refine_ls_R_factor_all          0.0257
_refine_ls_R_factor_gt           0.0252
_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^)+(0.0412P)^2^+0.1337P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0667
_refine_ls_wR_factor_ref         0.0672
_reflns_Friedel_coverage         0.871
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.963
_reflns_number_gt                3479
_reflns_number_total             3539
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc01166a2.cif
_cod_data_source_block           smghlc
_cod_depositor_comments
'Adding full bibliography for 7128130--7128133.cif.'
_cod_database_code               7128131
_nottingham_internal_coll_name   SMGHLC
_nottingham_internal_coll_number 18635
_nottingham_internal_coll_client SMG/HWL
_nottingham_internal_coll_type   custom
_nottingham_internal_coll_frame_method '\w scans'
_nottingham_internal_coll_frame_time '20.00, 5.00'
_nottingham_internal_coll_frame_width 1.00
_nottingham_internal_coll_user   pczspa
_nottingham_internal_coll_date   18/02/2020
_nottingham_internal_coll_location NOTTS
_nottingham_internal_coll_instrument 'GVB, PL13110001'
_nottingham_internal_process_date 19/02/2020
_nottingham_internal_process_user pczspa
_nottingham_internal_solution_date 19/02/2020
_nottingham_internal_solution_user pczspa
_nottingham_internal_refinement_date 19/02/2020
_nottingham_internal_refinement_user pczspa
_nottingham_internal_validation_date 19/02/2020
_nottingham_internal_validation_user pczspa
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C23H19FOS
_chemical_oxdiff_usercomment
'MNSLGF #186xx GVB-1776 for SLG/NRC in Fomblin film on a micromount'
_shelx_estimated_absorpt_t_max   0.955
_shelx_estimated_absorpt_t_min   0.757
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 C20A-C11 \\sim C20-C11
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C20 \\sim C21 \\sim C22 \\sim C23 \\sim C24 \\sim C25 \\sim F26 \\sim C20A
\\sim C21A \\sim C22A \\sim C23A \\sim C24A \\sim C25A \\sim F26A: within 2A
with sigma of 0.015 and sigma for terminal atoms of 0.03
Uanis(C20) = Uanis(C20A)
4. Rigid body (RIGU) restrains
 C20, C21, C22, C23, C24, C25, F26, C20A, C21A, C22A, C23A, C24A, C25A, F26A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Same fragment restrains
{C20, C21, C22, C23, C24, C25, F26} sigma for 1-2: 0.02, 1-3: 0.04
as
{C20A, C21A, C22A, C23A, C24A, C25A, F26A}
6. Others
 Sof(C20A)=Sof(C21A)=Sof(C22A)=Sof(H22A)=Sof(C23A)=Sof(H23A)=Sof(C24A)=
 Sof(H24A)=Sof(C25A)=Sof(H25A)=Sof(F26A)=1-FVAR(1)
 Sof(C20)=Sof(C21)=Sof(C22)=Sof(H22)=Sof(C23)=Sof(H23)=Sof(C24)=Sof(H24)=
 Sof(C25)=Sof(H25)=Sof(F26)=FVAR(1)
7.a Ternary CH refined with riding coordinates:
 C9(H9)
7.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C12(H12A,H12B), C13(H13A,H13B)
7.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C15(H15), C16(H16), C17(H17), C18(H18), C19(H19),
 C22(H22), C23(H23), C24(H24), C25(H25), C22A(H22A), C23A(H23A), C24A(H24A),
 C25A(H25A)
;
_shelx_res_checksum              51094
_olex2_exptl_crystal_mounting_method 'in fomblin film on a micromount'
_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 1.503
_oxdiff_exptl_absorpt_empirical_full_min 0.773