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_7121619
_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_formula_moiety         'C18 H19 N O3 S'
_chemical_formula_sum            'C18 H19 N O3 S'
_chemical_formula_weight         329.40
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2017-02-08
_audit_creation_method
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5292)
;
_audit_update_record
;
2017-11-10 deposited with the CCDC.
2018-05-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.2480(13)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.26646(16)
_cell_length_b                   6.72030(9)
_cell_length_c                   21.0219(3)
_cell_measurement_reflns_used    8951
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      73.6100
_cell_measurement_theta_min      4.2950
_cell_volume                     1561.08(4)
_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      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 5.2349
_diffrn_detector_type            'Agilent Diffraction Atlas S2 detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.984
_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    -35.00  30.00   1.00    2.00    --  -38.50  38.00  30.00   65
  2  \w     12.00  80.00   1.00    2.00    --   42.83  77.00 -30.00   68
  3  \w     75.00 101.00   1.00    8.00    --  104.50  81.00  16.06   26
  4  \w     74.00  99.00   1.00    8.00    --  104.50  77.00   0.00   25
  5  \w    110.00 177.00   1.00    8.00    --  104.50  77.00 -30.00   67
  6  \w    149.00 175.00   1.00    8.00    --  104.50  61.00  30.00   26
  7  \w    149.00 175.00   1.00    8.00    --  104.50  77.00   0.00   26
  8  \w    111.00 175.00   1.00    8.00    --  104.50  45.00  30.00   64
  9  \w     87.00 171.00   1.00    8.00    --  104.50  30.00  90.00   84
 10  \w     82.00 112.00   1.00    8.00    --  104.50  61.00  60.00   30
 11  \w     80.00 106.00   1.00    8.00    --  104.50  45.00  30.00   26
 12  \w     81.00 108.00   1.00    8.00    --  104.50  45.00  60.00   27
 13  \w     81.00 106.00   1.00    8.00    --  104.50  45.00   0.00   25
 14  \w     73.00 145.00   1.00    8.00    --  104.50  77.00 -60.00   72
 15  \w     74.00  99.00   1.00    8.00    --  104.50  77.00 -90.00   25
 16  \w     78.00 103.00   1.00    8.00    --  104.50  61.00 -60.00   25
 17  \w     77.00 103.00   1.00    8.00    --  104.50  61.00 -30.00   26
 18  \w     77.00 104.00   1.00    8.00    --  104.50  61.00  30.00   27
 19  \w     77.00 104.00   1.00    8.00    --  104.50  61.00   0.00   27
 20  \w     77.00 102.00   1.00    8.00    --  104.50  64.00 -19.73   25
 21  \w     75.00 102.00   1.00    8.00    --  104.50  77.00 -30.00   27
 22  \w     76.00 130.00   1.00    8.00    --  104.50  66.00 -62.66   54
 23  \w     74.00 101.00   1.00    8.00    --  104.50  77.00  30.00   27
 24  \w     77.00 104.00   1.00    8.00    --  104.50  59.00  -9.75   27
 25  \w     40.00  90.00   1.00    8.00    --  104.50 -45.00 -60.00   50
 26  \w     70.00 105.00   1.00    8.00    --  104.50 -94.00 -60.00   35
 27  \w     33.00  98.00   1.00    8.00    --  104.50 -45.00-120.00   65
 28  \w      6.00 121.00   1.00    2.00    --   42.83  19.00  60.00  115
 29  \w     53.00 136.00   1.00    8.00    --  104.50 -77.00 150.00   83
 30  \w     33.00  89.00   1.00    8.00    --  104.50 -45.00  90.00   56
 31  \w    -27.00  57.00   1.00    2.00    --   42.83 -38.00-120.00   84
 32  \w    -35.00  -8.00   1.00    2.00    --  -38.50  38.00-180.00   27
;
_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      0.1030827000
_diffrn_orient_matrix_UB_12      0.0884134000
_diffrn_orient_matrix_UB_13      0.0511986000
_diffrn_orient_matrix_UB_21      0.0828576000
_diffrn_orient_matrix_UB_22      0.0027247000
_diffrn_orient_matrix_UB_23      -0.0503045000
_diffrn_orient_matrix_UB_31      -0.0441213000
_diffrn_orient_matrix_UB_32      0.2114273000
_diffrn_orient_matrix_UB_33      -0.0207913000
_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  0.0299
_diffrn_reflns_av_unetI/netI     0.0232
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            14198
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.668
_diffrn_reflns_theta_min         4.154
_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    1.969
_exptl_absorpt_correction_T_max  0.937
_exptl_absorpt_correction_T_min  0.568
_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    1.402
_exptl_crystal_description       needle
_exptl_crystal_F_000             696
_exptl_crystal_recrystallization_method
'crystallised by diffusion of petroleum ether vapour into a colution of the compound in ethyl acetate'
_exptl_crystal_size_max          0.672
_exptl_crystal_size_mid          0.085
_exptl_crystal_size_min          0.036
_refine_diff_density_max         0.359
_refine_diff_density_min         -0.523
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         3105
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0364
_refine_ls_R_factor_gt           0.0347
_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^)+(0.0523P)^2^+0.7191P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0927
_refine_ls_wR_factor_ref         0.0946
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2916
_reflns_number_total             3105
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8cc03204a2.cif
_cod_data_source_block           tlnnla
_cod_depositor_comments
'Adding full bibliography for 7121617--7121623.cif.'
_cod_database_code               7121619
_nottingham_internal_coll_name   TLNNLA
_nottingham_internal_coll_number 16573
_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, 8.00'
_nottingham_internal_coll_frame_width 'in, 1.00'
_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 10/11/2016
_nottingham_internal_solution_user pczwl
_nottingham_internal_refinement_date 10/11/2016
_nottingham_internal_refinement_user pczwl
_nottingham_internal_validation_date 8/2/2017
_nottingham_internal_validation_user pczwl
_nottingham_internal_archive_date 8/2/2017
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C18 H19 N O3 S'
_chemical_oxdiff_usercomment
'TLNNLA #16573 GVB-1183 IN FOMBLIN FILM ON MICROMOUNT FOR TLNN/HWL'
_reflns_odcompleteness_completeness 99.90
_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), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7a,H7b), C14(H14a,H14b)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C9(H9), C10(H10), C18(H18), C19(H19), C21(H21), C22(H22)
2.d Idealised Me refined as rotating group:
 C8(H8a,H8b,H8c), C23(H23a,H23b,H23c)
;
_shelx_res_checksum              52958
_olex2_date_sample_data_collection 2016-10-19
_olex2_date_sample_submission    2016-10-18
_olex2_exptl_crystal_mounting_method 'in fomblin film on a micromount'
_olex2_submission_original_sample_id NH172
_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 1.572
_oxdiff_exptl_absorpt_empirical_full_min 0.535