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_7121618
_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         'C24 H23 Cl2 N O3 S'
_chemical_formula_sum            'C24 H23 Cl2 N O3 S'
_chemical_formula_weight         476.39
_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                 103.107(6)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.0371(6)
_cell_length_b                   8.0682(4)
_cell_length_c                   16.2367(10)
_cell_measurement_reflns_used    5017
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      75.7160
_cell_measurement_theta_min      5.0250
_cell_volume                     1153.03(12)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41n (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41n (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41n (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      N~2~
_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 0.983
_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   2.00    2.00    --  -38.50  38.00  60.00   42
  2  \w    -76.00 -36.00   2.00    2.00    --  -38.50 125.00 -60.00   20
  3  \w   -125.00  21.00   2.00    2.00    --  -38.50   0.00-120.00   73
  4  \w     36.00  98.00   2.00    2.00    --   43.32-125.00-150.00   31
  5  \w     40.00  66.00   2.00    2.00    --  108.63 -77.00 -30.00   13
  6  \w     90.00 118.00   2.00    2.00    --  108.63 -77.00 -30.00   14
  7  \w     61.00  95.00   2.00    2.00    --  108.63 -45.00-120.00   17
  8  \w     53.00 107.00   2.00    2.00    --  108.63 -95.00-180.00   27
  9  \w     46.00  84.00   2.00    2.00    --  108.63 -30.00-150.00   19
 10  \w     32.00 110.00   2.00    2.00    --  108.63 -95.00 -90.00   39
 11  \w     38.00 108.00   2.00    2.00    --  108.63-125.00-180.00   35
 12  \w     24.00  50.00   2.00    2.00    --   43.32-125.00 -60.00   13
 13  \w     42.00 122.00   2.00    2.00    --  108.63-125.00  60.00   40
 14  \w     55.00  85.00   2.00    2.00    --  108.63 -30.00  90.00   15
 15  \w     71.00 177.00   2.00    2.00    --  108.63  15.00  60.00   53
 16  \w    132.00 178.00   2.00    2.00    --  108.63  30.00 -60.00   23
 17  \w    108.00 176.00   2.00    2.00    --  108.63 117.00-143.00   34
 18  \w     97.00 177.00   2.00    2.00    --  108.63  45.00 120.00   40
 19  \w     37.00  99.00   2.00    2.00    --  108.63 -45.00 150.00   31
;
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'SuperNova-Duo, 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      0.0012543000
_diffrn_orient_matrix_UB_12      -0.1876211000
_diffrn_orient_matrix_UB_13      -0.0174433000
_diffrn_orient_matrix_UB_21      0.1468028000
_diffrn_orient_matrix_UB_22      0.0203470000
_diffrn_orient_matrix_UB_23      -0.0321551000
_diffrn_orient_matrix_UB_31      0.0949964000
_diffrn_orient_matrix_UB_32      -0.0289584000
_diffrn_orient_matrix_UB_33      0.0903111000
_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  0.0409
_diffrn_reflns_av_unetI/netI     0.0384
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8229
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.749
_diffrn_reflns_theta_min         5.025
_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    3.592
_exptl_absorpt_correction_T_max  0.481
_exptl_absorpt_correction_T_min  0.242
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41n (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    1.372
_exptl_crystal_description       block
_exptl_crystal_F_000             496
_exptl_crystal_recrystallization_method
'slow diffusion of petroleum ether vapor into an ethyl acetate solution of the compound'
_exptl_crystal_size_max          0.703
_exptl_crystal_size_mid          0.479
_exptl_crystal_size_min          0.268
_refine_diff_density_max         0.417
_refine_diff_density_min         -0.450
_refine_diff_density_rms         0.069
_refine_ls_abs_structure_details
;
 Flack x determined using 1893 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     292
_refine_ls_number_reflns         4600
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0512
_refine_ls_R_factor_gt           0.0501
_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^)+(0.0919P)^2^+0.2982P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1336
_refine_ls_wR_factor_ref         0.1354
_reflns_Friedel_coverage         0.815
_reflns_Friedel_fraction_full    0.993
_reflns_Friedel_fraction_max     0.929
_reflns_number_gt                4453
_reflns_number_total             4600
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8cc03204a2.cif
_cod_data_source_block           tlnnld
_cod_depositor_comments
'Adding full bibliography for 7121617--7121623.cif.'
_cod_database_code               7121618
_nottingham_internal_coll_name   TLNNLD
_nottingham_internal_coll_number 16576
_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 'SN, XDA 017/09'
_nottingham_internal_process_date 10/11/2016
_nottingham_internal_process_user pczwl
_nottingham_internal_solution_date 11/11/2016
_nottingham_internal_solution_user pczwl
_nottingham_internal_refinement_date 2/2/3017
_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         'C24 H23 Cl2 N O3 S'
_chemical_oxdiff_usercomment
'TLNNLD #16576 SN-1059 IN FOMBLIN ON MICROMOUNT FOR TLNN/HWL'
_shelx_estimated_absorpt_t_max   0.446
_shelx_estimated_absorpt_t_min   0.187
_reflns_odcompleteness_completeness 99.96
_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. Others
 Sof(H17)=Sof(Cl23)=1-FVAR(1)
 Sof(H19)=Sof(Cl21)=FVAR(1)
3.a Ternary CH refined with riding coordinates:
 C4(H4), C5(H5)
3.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C10(H10A,H10B)
3.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C16(H16), C17(H17), C19(H19), C20(H20), C26(H26), C27(H27),
 C29(H29), C30(H30)
3.d X=CH2 refined with riding coordinates:
 C14(H14A,H14B)
3.e Idealised Me refined as rotating group:
 C12(H12B,H12A,H12C), C31(H31A,H31B,H31C)
;
_shelx_res_checksum              65505
_olex2_date_sample_data_collection 2016-11-10
_olex2_date_sample_submission    2016-10-07
_olex2_exptl_crystal_mounting_method "'in fomblin film on a micromount"
_olex2_submission_original_sample_id NH167
_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 1.788
_oxdiff_exptl_absorpt_empirical_full_min 0.583