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_7121620
_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         'C28 H27 N O3 S'
_chemical_formula_sum            'C28 H27 N O3 S'
_chemical_formula_weight         457.56
_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'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.2814(7)
_cell_length_b                   12.1086(8)
_cell_length_c                   23.3936(12)
_cell_measurement_reflns_used    5679
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      74.0520
_cell_measurement_theta_min      3.6260
_cell_volume                     2345.8(3)
_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    'olex2.solve (Bourhis et al., 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_type            'Agilent Diffraction Titan S2 detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.982
_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    -28.00 110.00   2.00    2.00    --   43.31   0.00 -90.00   69
  2  \w     83.00 149.00   2.00    2.00    --  103.95  61.00 -60.00   33
  3  \w     98.00 174.00   2.00    2.00    --  103.95 125.00 -60.00   38
  4  \w     74.00 136.00   2.00    2.00    --  103.95  77.00  90.00   31
  5  \w     55.00  83.00   2.00    2.00    --   43.31 159.00 -92.00   14
  6  \w    -18.00   8.00   2.00    2.00    --  -43.31  38.00-120.00   13
  7  \w     56.00  96.00   2.00    2.00    --  103.95 -45.00 -60.00   20
  8  \w     39.00  91.00   2.00    2.00    --  103.95 -30.00-180.00   26
  9  \w     33.00  71.00   2.00    2.00    --  103.95 -30.00-120.00   19
 10  \w     33.00  87.00   2.00    2.00    --  103.95 -30.00 -90.00   27
;
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'SuperNova, Titan S2'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1226399000
_diffrn_orient_matrix_UB_12      0.0392204000
_diffrn_orient_matrix_UB_13      -0.0451460000
_diffrn_orient_matrix_UB_21      -0.0202149000
_diffrn_orient_matrix_UB_22      0.1197720000
_diffrn_orient_matrix_UB_23      0.0209752000
_diffrn_orient_matrix_UB_31      0.1384144000
_diffrn_orient_matrix_UB_32      -0.0172360000
_diffrn_orient_matrix_UB_33      0.0431310000
_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_radiation_xray_symbol    K-L~2,3~
_diffrn_reflns_av_R_equivalents  0.0311
_diffrn_reflns_av_unetI/netI     0.0361
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            9059
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.091
_diffrn_reflns_theta_min         3.779
_diffrn_source_current           0.8
_diffrn_source_power             0.04
_diffrn_source_target            Cu
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    1.465
_exptl_absorpt_correction_T_max  0.744
_exptl_absorpt_correction_T_min  0.488
_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    1.296
_exptl_crystal_description       block
_exptl_crystal_F_000             968
_exptl_crystal_recrystallization_method
'slow diffusion of petroleum ether vapor into an theyl acetate solution of the compound'
_exptl_crystal_size_max          0.609
_exptl_crystal_size_mid          0.459
_exptl_crystal_size_min          0.232
_refine_diff_density_max         0.246
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details
;
 Flack x determined using 1792 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.064(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     404
_refine_ls_number_reflns         4616
_refine_ls_number_restraints     164
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0365
_refine_ls_R_factor_gt           0.0355
_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^)+(0.0493P)^2^+0.3773P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0903
_refine_ls_wR_factor_ref         0.0913
_reflns_Friedel_coverage         0.724
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.946
_reflns_number_gt                4500
_reflns_number_total             4616
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8cc03204a2.cif
_cod_data_source_block           tlnnle
_cod_depositor_comments
'Adding full bibliography for 7121617--7121623.cif.'
_cod_database_code               7121620
_nottingham_internal_coll_name   TLNNLE
_nottingham_internal_coll_number 16577
_nottingham_internal_coll_client TLNN/HWL
_nottingham_internal_coll_type   custom
_nottingham_internal_coll_frame_method 'ofand \w scans'
_nottingham_internal_coll_frame_time 'degrees,, 2.00'
_nottingham_internal_coll_frame_width 'in, 2.00'
_nottingham_internal_coll_user   pczwl
_nottingham_internal_coll_date   20/10/2016
_nottingham_internal_coll_location NOTTS
_nottingham_internal_coll_instrument 'GVA, PL13110002'
_nottingham_internal_process_date 14/11/2016
_nottingham_internal_process_user pczwl
_nottingham_internal_solution_date 15/11/2016
_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         'C28 H27 N O3 S'
_chemical_oxdiff_usercomment
'TLNNLE #16577 GVA-1085 IN FOMBLIN FILM ON MICROMOUNT FOR TLNN/HWL'
_shelx_estimated_absorpt_t_max   0.727
_shelx_estimated_absorpt_t_min   0.469
_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
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C16-C15 \\sim C16A-C15A
 with sigma of 0.02
 C24-C15 \\sim C24A-C15A
 with sigma of 0.02
 C24A-C23A \\sim C24-C23
 with sigma of 0.02
 C17A-C16A \\sim C17-C16
 with sigma of 0.02
 C23A-C22A \\sim C23-C22
 with sigma of 0.02
 C22-C17 \\sim C22A-C17A
 with sigma of 0.02
 C18-C17 \\sim C18A-C17A
 with sigma of 0.02
 C19-C18 \\sim C19A-C18A
 with sigma of 0.02
 C22-C21 \\sim C22A-C21A
 with sigma of 0.02
 C20A-C19A \\sim C20-C19
 with sigma of 0.02
 C21-C20 \\sim C21A-C20A
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C13A \\sim C14A \\sim C16A \\sim C15A \\sim C24A \\sim C23A \\sim C22A \\sim
C17A \\sim C18A \\sim C19A \\sim C20A \\sim C21A: within 2A with sigma of 0.01
and sigma for terminal atoms of 0.02
4. Rigid body (RIGU) restrains
 C13A, C14A, C16A, C15A, C24A, C23A, C22A, C17A, C18A, C19A, C20A, C21A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(H5B)=Sof(C13A)=Sof(C14A)=Sof(H14C)=Sof(H14D)=Sof(C15A)=Sof(C16A)=
 Sof(H16A)=Sof(C17A)=Sof(C18A)=Sof(H18A)=Sof(C19A)=Sof(H19A)=Sof(C20A)=
 Sof(H20A)=Sof(C21A)=Sof(H21A)=Sof(C22A)=Sof(C23A)=Sof(H23A)=Sof(C24A)=
 Sof(H24A)=1-FVAR(1)
 Sof(H5A)=Sof(C13)=Sof(C14)=Sof(H14A)=Sof(H14B)=Sof(C15)=Sof(C16)=Sof(H16)=
 Sof(C17)=Sof(C18)=Sof(H18)=Sof(C19)=Sof(H19)=Sof(C20)=Sof(H20)=Sof(C21)=
 Sof(H21)=Sof(C22)=Sof(C23)=Sof(H23)=Sof(C24)=Sof(H24)=FVAR(1)
6.a Ternary CH refined with riding coordinates:
 C4(H4), C5(H5A), C5(H5B)
6.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C10(H10A,H10B)
6.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C16(H16), C16A(H16A), C18(H18), C18A(H18A), C19(H19),
 C19A(H19A), C20(H20), C20A(H20A), C21(H21), C21A(H21A), C23(H23), C23A(H23A),
 C24(H24), C24A(H24A), C28(H28), C29(H29), C31(H31), C32(H32)
6.d X=CH2 refined with riding coordinates:
 C14(H14A,H14B), C14A(H14C,H14D)
6.e Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C33(H33A,H33B,H33C)
;
_shelx_res_checksum              20826
_olex2_date_sample_data_collection 2016-11-14
_olex2_date_sample_submission    2016-10-07
_olex2_exptl_crystal_mounting_method "'in fomblin film on a micromount"
_olex2_submission_original_sample_id NH168
_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 2.137
_oxdiff_exptl_absorpt_empirical_full_min 0.589