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_7121622
_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         'C22 H23 N O3 S2'
_chemical_formula_sum            'C23.5 H26.5 N O3 S2'
_chemical_formula_weight         435.08
_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     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                 111.4791(15)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.72773(19)
_cell_length_b                   8.01122(7)
_cell_length_c                   18.9065(3)
_cell_measurement_reflns_used    20407
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      73.4230
_cell_measurement_theta_min      4.5540
_cell_volume                     2216.75(5)
_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 Atlas S2 detector'
_diffrn_measured_fraction_theta_full 0.999
_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    -50.00  34.00   1.00    4.00    --  -38.50  38.00   0.00   84
  2  \w      2.00  98.00   1.00    4.00    --   43.08-125.00-150.00   96
  3  \w      2.00  98.00   1.00    4.00    --   43.08-125.00   0.00   96
  4  \w     23.00 109.00   1.00   16.00    --  104.50 -94.00 120.00   86
  5  \w     30.00  91.00   1.00   16.00    --  104.50 -30.00 -60.00   61
  6  \w     33.00 122.00   1.00   16.00    --  104.50-125.00 -90.00   89
  7  \w     81.00 178.00   1.00   16.00    --  104.50  30.00 -30.00   97
  8  \w     30.00  91.00   1.00   16.00    --  104.50 -30.00-180.00   61
  9  \w     73.00 176.00   1.00   16.00    --  104.50 125.00-120.00  103
 10  \w     80.00 176.00   1.00   16.00    --  104.50  45.00-150.00   96
 11  \w     16.00 113.00   1.00    4.00    --   43.08  57.00 150.00   97
 12  \w     16.00 113.00   1.00    4.00    --   43.08  57.00 -90.00   97
 13  \w     12.00 117.00   1.00    4.00    --   43.08  77.00  30.00  105
 14  \w     80.00 176.00   1.00   16.00    --  104.50  45.00  30.00   96
 15  \w     23.00 109.00   1.00   16.00    --  104.50 -94.00 -30.00   86
 16  \w     77.00 175.00   1.00   16.00    --  104.50  61.00 -90.00   98
 17  \w     33.00  98.00   1.00   16.00    --  104.50 -45.00 120.00   65
 18  \w     73.00 178.00   1.00   16.00    --  104.50  77.00 150.00  105
 19  \w     81.00 178.00   1.00   16.00    --  104.50  30.00 120.00   97
 20  \w    -50.00  34.00   1.00    4.00    --  -38.50  38.00  90.00   84
 21  \w     12.00 117.00   1.00    4.00    --   43.08  77.00 -60.00  105
 22  \w     12.00 117.00   1.00    4.00    --   43.08  77.00-180.00  105
 23  \w     77.00 125.00   1.00   16.00    --  104.50  61.00 -30.00   48
 24  \w     73.00 178.00   1.00   16.00    --  104.50  77.00-150.00  105
 25  \w     77.00 175.00   1.00   16.00    --  104.50  61.00  60.00   98
;
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'SuperNova, Atlas'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0564639000
_diffrn_orient_matrix_UB_12      -0.1622784000
_diffrn_orient_matrix_UB_13      -0.0187621000
_diffrn_orient_matrix_UB_21      0.0377282000
_diffrn_orient_matrix_UB_22      -0.0399428000
_diffrn_orient_matrix_UB_23      -0.0626631000
_diffrn_orient_matrix_UB_31      0.0803387000
_diffrn_orient_matrix_UB_32      -0.0953288000
_diffrn_orient_matrix_UB_33      0.0582336000
_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  0.0392
_diffrn_reflns_av_unetI/netI     0.0305
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            32097
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.844
_diffrn_reflns_theta_min         4.583
_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    2.374
_exptl_absorpt_correction_T_max  0.928
_exptl_absorpt_correction_T_min  0.590
_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    1.304
_exptl_crystal_description       needle
_exptl_crystal_F_000             922
_exptl_crystal_recrystallization_method
'slow diffusion of petroleum ether vapor into an ethyl acetate solution of the compound'
_exptl_crystal_size_max          0.485
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.034
_refine_diff_density_max         0.397
_refine_diff_density_min         -0.466
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details
;
 Flack x determined using 3675 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.020(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     528
_refine_ls_number_reflns         8753
_refine_ls_number_restraints     577
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.0368
_refine_ls_R_factor_gt           0.0354
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0550P)^2^+0.4678P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0914
_refine_ls_wR_factor_ref         0.0930
_reflns_Friedel_coverage         0.834
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.961
_reflns_number_gt                8447
_reflns_number_total             8753
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8cc03204a2.cif
_cod_data_source_block           tlnnlg_sq
_cod_depositor_comments
'Adding full bibliography for 7121617--7121623.cif.'
_cod_original_formula_sum        'C23.50 H26.50 N O3 S2'
_cod_database_code               7121622
_nottingham_internal_coll_name   TLNNLG
_nottingham_internal_coll_number 16579
_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,, 4.00, 16.00'
_nottingham_internal_coll_frame_width 'in, 1.00'
_nottingham_internal_coll_user   pczwl
_nottingham_internal_coll_date   20/10/2016
_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 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
_platon_squeeze_void_probe_radius 1.20
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         'C22 H23 N O3 S2'
_chemical_oxdiff_usercomment
'TLNNLG #165679 GVB-1188 IN FOMBLIN FILM ON MICROMOUNT FOR TLNN/HWL'
_reflns_odcompleteness_completeness 99.93
_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
 S48A-C47A \\sim S47-C48 \\sim S17-C18
 with sigma of 0.02
 C46-C47A \\sim C49-C48 \\sim C19-C18
 with sigma of 0.02
 S17-C16 \\sim S47-C46 \\sim S48A-C49
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C45 \\sim C46 \\sim S47 \\sim C47A \\sim C48 \\sim S48A \\sim C49: within 2A
with sigma of 0.01 and sigma for terminal atoms of 0.02
4. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(H46A)=Sof(C47A)=Sof(H47A)=Sof(S48A)=Sof(H49A)=1-FVAR(1)
 Sof(H46)=Sof(S47)=Sof(C48)=Sof(H48)=Sof(H49)=FVAR(1)
6.a Ternary CH refined with riding coordinates:
 C4(H4), C5(H5), C34(H34), C35(H35)
6.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C10(H10A,H10B), C36(H36A,H36B), C40(H40A,H40B)
6.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C16(H16), C18(H18), C19(H19), C23(H23), C24(H24), C26(H26),
 C27(H27), C37(H37), C38(H38), C46(H46), C46(H46A), C47A(H47A), C48(H48),
 C49(H49), C49(H49A), C53(H53), C54(H54), C56(H56), C57(H57)
6.d X=CH2 refined with riding coordinates:
 C14(H14A,H14B), C44(H44A,H44B)
6.e Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C28(H28A,H28B,H28C), C42(H42A,H42B,H42C), C58(H58A,H58B,
 H58C)
;
_shelx_res_checksum              77947
_shelx_fab_checksum              11292
_olex2_date_sample_data_collection 2016-10-20
_olex2_date_sample_submission    2016-10-18
_olex2_exptl_crystal_mounting_method "'in fomblin film on a micromount"
_olex2_submission_original_sample_id NH178
_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 1.737
_oxdiff_exptl_absorpt_empirical_full_min 0.609