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_7128130
_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         'C25 H21 F O'
_chemical_formula_sum            'C25 H21 F O'
_chemical_formula_weight         356.42
_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             2019-09-04
_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                 110.215(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.9239(4)
_cell_length_b                   5.6798(2)
_cell_length_c                   14.6714(6)
_cell_measurement_reflns_used    3624
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      72.8170
_cell_measurement_theta_min      3.9380
_cell_volume                     932.42(6)
_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 10.3613
_diffrn_detector_type            'Agilent Diffraction Atlas detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.979
_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    -92.00 -54.00   1.00    1.00    --  -38.50-154.00-112.00   38
  2  \w      3.00  32.00   1.00    1.00    --  -38.50  38.00-150.00   29
  3  \w    -49.00  33.00   1.00    1.00    --  -38.50  38.00 -90.00   82
  4  \w    -44.00  31.00   1.00    1.00    --  -38.50  38.00-180.00   75
  5  \w     20.00  82.00   1.00    1.00    --   43.50 -99.00 -60.00   62
  6  \w    -22.00  63.00   1.00    1.00    --   43.50 -38.00   0.00   85
  7  \w     35.00  84.00   1.00    4.00    --  103.63 -95.00 -90.00   49
  8  \w     24.00 142.00   1.00    4.00    --  103.63 -15.00 120.00  118
  9  \w    131.00 177.00   1.00    4.00    --  103.63  30.00 -60.00   46
 10  \w     29.00  58.00   1.00    4.00    --  103.63 -30.00 -60.00   29
 11  \w     31.00  81.00   1.00    4.00    --  103.63 -30.00-120.00   50
 12  \w     61.00 116.00   1.00    4.00    --  103.63-125.00   0.00   55
 13  \w     34.00  91.00   1.00    4.00    --  103.63 -30.00  30.00   57
 14  \w     37.00  90.00   1.00    4.00    --  103.63 -30.00 -30.00   53
 15  \w     33.00 121.00   1.00    4.00    --  103.63 -61.00 120.00   88
 16  \w     80.00 117.00   1.00    4.00    --  103.63-125.00-180.00   37
 17  \w     38.00 127.00   1.00    4.00    --  103.63 -77.00   0.00   89
 18  \w     68.00  93.00   1.00    4.00    --  103.63 -95.00-150.00   25
;
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'SuperNova, Atlas'
_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      -0.0284152000
_diffrn_orient_matrix_UB_12      -0.2653095000
_diffrn_orient_matrix_UB_13      -0.0050101000
_diffrn_orient_matrix_UB_21      -0.0320193000
_diffrn_orient_matrix_UB_22      0.0055488000
_diffrn_orient_matrix_UB_23      -0.1111138000
_diffrn_orient_matrix_UB_31      0.1308231000
_diffrn_orient_matrix_UB_32      -0.0561041000
_diffrn_orient_matrix_UB_33      0.0123817000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0221
_diffrn_reflns_av_unetI/netI     0.0280
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            6375
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.140
_diffrn_reflns_theta_min         3.210
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_type              'Agilent Diffraction microfocus tube'
_exptl_absorpt_coefficient_mu    0.657
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.645
_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    1.269
_exptl_crystal_description       block
_exptl_crystal_F_000             376
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: pentane, Et2O'
_exptl_crystal_size_max          0.421
_exptl_crystal_size_mid          0.168
_exptl_crystal_size_min          0.066
_refine_diff_density_max         0.128
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details
;
 Flack x determined using 1428 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3582
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0347
_refine_ls_R_factor_gt           0.0328
_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^)+(0.0538P)^2^+0.2275P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0820
_refine_ls_wR_factor_ref         0.0841
_reflns_Friedel_coverage         0.776
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.941
_reflns_number_gt                3405
_reflns_number_total             3582
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc01166a2.cif
_cod_data_source_block           smghlb
_cod_depositor_comments
'Adding full bibliography for 7128130--7128133.cif.'
_cod_database_code               7128130
_nottingham_internal_coll_name   SMGHLB
_nottingham_internal_coll_number 18405
_nottingham_internal_coll_client SMG/HWL
_nottingham_internal_coll_type   custom
_nottingham_internal_coll_frame_method '\w scans'
_nottingham_internal_coll_frame_time '1.00, 4.00'
_nottingham_internal_coll_frame_width 1.00
_nottingham_internal_coll_user   pczspa
_nottingham_internal_coll_date   02/09/2019
_nottingham_internal_coll_location NOTTS
_nottingham_internal_coll_instrument 'SN, XDA 017-09'
_nottingham_internal_process_date 02/09/2019
_nottingham_internal_process_user pczspa
_nottingham_internal_solution_date 04/09/2019
_nottingham_internal_solution_user pczspa
_nottingham_internal_refinement_date 04/09/2019
_nottingham_internal_refinement_user pczspa
_nottingham_internal_validation_date 04/09/2019
_nottingham_internal_validation_user pczspa
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         C25H21F1O1
_chemical_oxdiff_usercomment
'SMGHLB #SN-1524 FOMBLIM ON MICROMOUNT FOR SMG/HWL'
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     67.13
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C14(H14A,H14B), C15(H15A,H15B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C17(H17), C18(H18), C19(H19), C20(H20),
 C21(H21), C23(H23), C24(H24), C25(H25), C26(H26), C27(H27)
;
_shelx_res_checksum              90331
_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 1.300
_oxdiff_exptl_absorpt_empirical_full_min 0.797