Enantioselective nickel-catalyzed arylative intramolecular 1,4-allylations.
Nguyen, Thi Le Nhon; Incerti-Pradillos, Celia A; Lewis, William; Lam, Hon Wai; Chemical communications (Cambridge, England) 54 (2018) 5622–5625; doi:10.1039/c8cc03204a

data_7121621
_publ_section_title
;
 Enantioselective nickel-catalyzed arylative intramolecular
 1,4-allylations.
;
_journal_issue                   44
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              5622
_journal_page_last               5625
_journal_paper_doi               10.1039/c8cc03204a
_journal_volume                  54
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C26 H27 N O3 S'
_chemical_formula_sum            'C26 H27 N O3 S'
_chemical_formula_weight         433.54
_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'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2017-08-24
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2017-11-10 deposited with the CCDC.
2018-05-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.441(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.3854(3)
_cell_length_b                   8.06169(18)
_cell_length_c                   23.0268(5)
_cell_measurement_reflns_used    31224
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      73.5260
_cell_measurement_theta_min      3.5780
_cell_volume                     2292.26(9)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (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    'ShelXS (Sheldrick, 2008)'
_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 1.000
_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   -109.00 -13.00   2.00    2.00    --  -38.50 -57.00   0.00   48
  2  \w    -70.00  36.00   2.00    2.00    --  -38.50  79.00 133.00   53
  3  \w    -50.00  34.00   2.00    2.00    --  -38.50  38.00 -90.00   42
  4  \w     20.00 114.00   2.00    2.00    --   42.83  38.00 -90.00   47
  5  \w     30.00  90.00   2.00    3.00    --  104.50 -30.00 -60.00   30
  6  \w     80.00 176.00   2.00    3.00    --  104.50  45.00 -90.00   48
  7  \w     59.00 177.00   2.00    3.00    --  104.50  15.00-120.00   59
  8  \w     23.00 109.00   2.00    3.00    --  104.50 -94.00-120.00   43
  9  \w     30.00  90.00   2.00    3.00    --  104.50 -30.00  90.00   30
 10  \w     30.00  90.00   2.00    3.00    --  104.50 -30.00 -90.00   30
 11  \w     80.00 176.00   2.00    3.00    --  104.50  45.00 -60.00   48
 12  \w     33.00 121.00   2.00    3.00    --  104.50-125.00  90.00   44
 13  \w     80.00 176.00   2.00    3.00    --  104.50  45.00  90.00   48
 14  \w     31.00 135.00   2.00    3.00    --  104.50 -77.00  90.00   52
 15  \w     30.00  90.00   2.00    3.00    --  104.50 -30.00-180.00   30
 16  \w     33.00  97.00   2.00    3.00    --  104.50 -45.00   0.00   32
 17  \w     31.00 135.00   2.00    3.00    --  104.50 -77.00 -90.00   52
 18  \w     11.00 117.00   2.00    2.00    --   42.83  77.00-150.00   53
 19  \w     11.00 117.00   2.00    2.00    --   42.83  77.00 -60.00   53
 20  \w     16.00 112.00   2.00    2.00    --   42.83  57.00 150.00   48
 21  \w    -20.00  82.00   2.00    2.00    --   42.83 -99.00   0.00   51
 22  \w     11.00 117.00   2.00    2.00    --   42.83  77.00  30.00   53
 23  \w     73.00 177.00   2.00    3.00    --  104.50  77.00 120.00   52
 24  \w     73.00 177.00   2.00    3.00    --  104.50  77.00  90.00   52
 25  \w     77.00 175.00   2.00    3.00    --  104.50  61.00   0.00   49
 26  \w     73.00 177.00   2.00    3.00    --  104.50  77.00 150.00   52
 27  \w     73.00 177.00   2.00    3.00    --  104.50  77.00-150.00   52
 28  \w     77.00 175.00   2.00    3.00    --  104.50  61.00 -30.00   49
 29  \w     73.00 177.00   2.00    3.00    --  104.50  77.00-180.00   52
 30  \w     77.00 175.00   2.00    3.00    --  104.50  61.00 -60.00   49
 31  \w     77.00 175.00   2.00    3.00    --  104.50  61.00  30.00   49
 32  \w     73.00 177.00   2.00    3.00    --  104.50  77.00  30.00   52
 33  \w     11.00  97.00   2.00    2.00    --   42.83  77.00 120.00   43
;
_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      -0.0696210000
_diffrn_orient_matrix_UB_12      0.0522092000
_diffrn_orient_matrix_UB_13      -0.0553570000
_diffrn_orient_matrix_UB_21      0.0716765000
_diffrn_orient_matrix_UB_22      0.1543834000
_diffrn_orient_matrix_UB_23      -0.0055177000
_diffrn_orient_matrix_UB_31      0.0746832000
_diffrn_orient_matrix_UB_32      -0.0997988000
_diffrn_orient_matrix_UB_33      -0.0375569000
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_wavelength_determination fundamental
_diffrn_reflns_av_R_equivalents  0.0408
_diffrn_reflns_av_unetI/netI     0.0234
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            45379
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.946
_diffrn_reflns_theta_min         3.579
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_current           0.8
_diffrn_source_power             0.04
_diffrn_source_target            Cu
_diffrn_source_type              'Agilent Diffraction microfocus tube'
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    1.468
_exptl_absorpt_correction_T_max  0.814
_exptl_absorpt_correction_T_min  0.530
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
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            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.256
_exptl_crystal_description       block
_exptl_crystal_F_000             920
_exptl_crystal_recrystallization_method
'diffusion of petroleum ether vapor into an ethyl acetate solution of the compound'
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.346
_exptl_crystal_size_min          0.204
_refine_diff_density_max         0.180
_refine_diff_density_min         -0.399
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details
;
 Flack x determined using 4029 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.022(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     563
_refine_ls_number_reflns         9141
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0338
_refine_ls_R_factor_gt           0.0333
_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^)+(0.0492P)^2^+0.6137P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0869
_refine_ls_wR_factor_ref         0.0872
_reflns_Friedel_coverage         0.847
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.974
_reflns_number_gt                9052
_reflns_number_total             9141
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8cc03204a2.cif
_cod_data_source_block           tlnnlc
_cod_depositor_comments
'Adding full bibliography for 7121617--7121623.cif.'
_cod_original_cell_volume        2292.27(9)
_cod_database_code               7121621
_nottingham_internal_coll_name   TLNNLC
_nottingham_internal_coll_number 16575
_nottingham_internal_coll_client TLNN/HWL
_nottingham_internal_coll_type   custom
_nottingham_internal_coll_frame_method '\w scans'
_nottingham_internal_coll_frame_time '2.00, 3.00'
_nottingham_internal_coll_frame_width 2.00
_nottingham_internal_coll_user   pczwl
_nottingham_internal_coll_date   19/10/2016
_nottingham_internal_coll_location NOTTS
_nottingham_internal_coll_instrument 'GVB, PL13110001'
_nottingham_internal_process_date 07/11/2016
_nottingham_internal_process_user pczwl
_nottingham_internal_solution_date 8/11/2016
_nottingham_internal_solution_user pczwl
_nottingham_internal_refinement_date 2/2/2017
_nottingham_internal_refinement_user pczwl
_nottingham_internal_validation_date 24/8/2017
_nottingham_internal_validation_user pczwl
_nottingham_internal_archive_date 24/8/2017
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         'C26 H27 N O3 S'
_chemical_oxdiff_usercomment
'TLNNLC #16575 GVB-1184 IN FOMBLIN FILM ON MICROMOUNT FOR TLNN/HWL'
_shelx_estimated_absorpt_t_max   0.754
_shelx_estimated_absorpt_t_min   0.473
_reflns_odcompleteness_completeness 99.98
_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
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C4(H4), C5(H5), C44(H44), C45(H45)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C10(H10A,H10B), C46(H46A,H46B), C50(H50A,H50B)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C16(H16), C17(H17), C19(H19), C20(H20), C21(H21), C26(H26),
 C27(H27), C29(H29), C30(H30), C47(H47), C48(H48), C56(H56), C57(H57), C59(H59),
  C60(H60), C61(H61), C66(H66), C67(H67), C69(H69), C70(H70)
2.d X=CH2 refined with riding coordinates:
 C14(H14A,H14B), C22(H22A,H22B), C54(H54A,H54B), C62(H62A,H62B)
2.e Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C31(H31A,H31B,H31C), C52(H52A,H52B,H52C), C71(H71A,H71B,
 H71C)
;
_shelx_res_checksum              35433
_olex2_date_sample_data_collection 2016-11-07
_olex2_date_sample_submission    2016-10-18
_olex2_exptl_crystal_mounting_method "'in fomblin film on a micromount"
_olex2_submission_original_sample_id NH166
_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 1.655
_oxdiff_exptl_absorpt_empirical_full_min 0.604