Highly Enantioselective Nickel-Catalyzed Intramolecular Hydroalkenylation of N- and O-Tethered 1,6-Dienes To Form Six-Membered Heterocycles.
Li, Ke; Li, Mao-Lin; Zhang, Qi; Zhu, Shou-Fei; Zhou, Qi-Lin; Journal of the American Chemical Society 140 (2018) 7458–7461; doi:10.1021/jacs.8b04703

data_4132536
_publ_section_title
;
 Highly Enantioselective Nickel-Catalyzed Intramolecular Hydroalkenylation
 of N- and O-Tethered 1,6-Dienes To Form Six-Membered Heterocycles.
;
_journal_issue                   24
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              7458
_journal_page_last               7461
_journal_paper_doi               10.1021/jacs.8b04703
_journal_volume                  140
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C19 H21 N O2 S'
_chemical_formula_sum            'C19 H21 N O2 S'
_chemical_formula_weight         327.43
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-05-17
_audit_creation_method
;
Olex2 1.2-ac21
(compiled 2015.09.16 svn.r134, GUI svn.r4998)
;
_cell_angle_alpha                90
_cell_angle_beta                 115.687(6)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.6458(3)
_cell_length_b                   26.6994(9)
_cell_length_c                   6.1070(2)
_cell_measurement_reflns_used    4969
_cell_measurement_temperature    113.15
_cell_measurement_theta_max      31.1130
_cell_measurement_theta_min      3.0600
_cell_volume                     829.59(7)
_computing_cell_refinement
;
CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)
;
_computing_data_collection
;
CrystalClear-SM Expert 2.1 b42 (Rigaku, 2015)
;
_computing_data_reduction
;
CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      113.15
_diffrn_detector                 PILT
_diffrn_detector_area_resol_mean 5.814
_diffrn_detector_type            'Rigaku Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.904
_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   -120.00  60.00   0.50    5.00    --  -30.00  45.00   0.00  360
  2  \w   -120.00  60.00   0.50    5.00    --  -30.00  45.00  90.00  360
  3  \w   -120.00  60.00   0.50    5.00    --  -30.00  45.00 180.00  360
;
_diffrn_measurement_device       'AFC10: Fixed Chi 2 circle'
_diffrn_measurement_device_type  'Rigaku Xtalab P200'
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0184478000
_diffrn_orient_matrix_UB_12      0.0121430000
_diffrn_orient_matrix_UB_13      -0.1095816000
_diffrn_orient_matrix_UB_21      -0.0039276000
_diffrn_orient_matrix_UB_22      0.0235304000
_diffrn_orient_matrix_UB_23      0.0521054000
_diffrn_orient_matrix_UB_31      0.1381716000
_diffrn_orient_matrix_UB_32      0.0022993000
_diffrn_orient_matrix_UB_33      0.0433184000
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0197
_diffrn_reflns_av_unetI/netI     0.0318
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.904
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            8060
_diffrn_reflns_point_group_measured_fraction_full 0.909
_diffrn_reflns_point_group_measured_fraction_max 0.802
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         31.566
_diffrn_reflns_theta_min         1.525
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'Rotating Anode'
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.204
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.42241
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_description       plate
_exptl_crystal_F_000             348
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.504
_refine_diff_density_min         -0.521
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details
;
 Flack x determined using 1698 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         4450
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0382
_refine_ls_R_factor_gt           0.0364
_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^)+(0.0700P)^2^+0.0330P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1020
_refine_ls_wR_factor_ref         0.1030
_reflns_Friedel_coverage         0.741
_reflns_Friedel_fraction_full    0.830
_reflns_Friedel_fraction_max     0.696
_reflns_number_gt                4227
_reflns_number_total             4450
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b04703_si_002.cif
_cod_data_source_block           m20160518b
_cod_original_cell_volume        829.58(7)
_cod_database_code               4132536
_chemical_oxdiff_formula         C19H21NO2S
_shelx_estimated_absorpt_t_max   0.976
_shelx_estimated_absorpt_t_min   0.937
_reflns_odcompleteness_completeness 90.44
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     31.49
_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:
 C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C4(H4A,H4B), C5(H5A,H5B)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C10(H10), C11(H11), C12(H12), C14(H14), C15(H15), C17(H17),
 C18(H18)
2.d X=CH2 refined with riding coordinates:
 C6(H6A,H6B)
2.e Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C)
;
_shelx_res_checksum              65106
_shelx_hkl_checksum              82573
_shelx_shelxl_version_number     2014/8
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.789
_oxdiff_exptl_absorpt_empirical_full_min 0.446