Enantioselective Ni-Al Bimetallic Catalyzed exo-Selective C-H Cyclization of Imidazoles with Alkenes.
Wang, Yin-Xia; Qi, Shao-Long; Luan, Yu-Xin; Han, Xing-Wang; Wang, Shan; Chen, Hao; Ye, Mengchun; Journal of the American Chemical Society 140 (2018) 5360–5364; doi:10.1021/jacs.8b02547

data_4132241
_publ_section_title
;
 Enantioselective Ni-Al Bimetallic Catalyzed exo-Selective C-H Cyclization
 of Imidazoles with Alkenes.
;
_journal_issue                   16
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              5360
_journal_page_last               5364
_journal_paper_doi               10.1021/jacs.8b02547
_journal_volume                  140
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C18 H18 N2'
_chemical_formula_sum            'C18 H18 N2'
_chemical_formula_weight         262.34
_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             2016-12-29
_audit_creation_method
;
Olex2 1.2-ac21
(compiled 2015.09.16 svn.r134, GUI svn.r4998)
;
_cell_angle_alpha                90
_cell_angle_beta                 97.6815(17)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.57436(15)
_cell_length_b                   6.43605(18)
_cell_length_c                   13.5714(3)
_cell_measurement_reflns_used    8310
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      78.7900
_cell_measurement_theta_min      3.2850
_cell_volume                     742.22(3)
_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      294.15
_diffrn_detector                 PILT
_diffrn_detector_area_resol_mean 5.814
_diffrn_detector_type            'Rigaku Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.980
_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  55.00   1.00    5.00    --  -35.00  43.00-180.00  105
  2  \w   -114.00 -21.00   1.00    5.00    --  -35.00 -72.00-108.00   93
  3  \w   -125.00 -32.00   1.00    5.00    --  -35.00 -72.00-180.00   93
  4  \w   -114.00 -21.00   1.00    5.00    --  -35.00 -44.00-108.00   93
  5  \w   -115.00 -25.00   1.00    5.00    --  -35.00 -72.00-144.00   90
  6  \w    -50.00  40.00   1.00    5.00    --  -35.00  72.00-144.00   90
  7  \w   -112.00 -21.00   1.00    5.00    --  -35.00 -72.00 144.00   91
  8  \w   -125.00 -33.00   1.00    5.00    --  -35.00 -44.00 -36.00   92
  9  \w   -125.00 -33.00   1.00    5.00    --  -35.00 -72.00 -72.00   92
 10  \w   -200.00 -96.00   1.00    5.00    -- -110.00 -72.00 144.00  104
 11  \w   -187.00 -96.00   1.00    5.00    -- -110.00 -44.00-108.00   91
 12  \w   -187.00 -96.00   1.00    5.00    -- -110.00 -72.00-144.00   91
 13  \w   -125.00 -33.00   1.00    5.00    -- -110.00  72.00-108.00   92
 14  \w   -200.00-110.00   1.00    5.00    -- -110.00 -15.00 144.00   90
 15  \w   -187.00 -96.00   1.00    5.00    -- -110.00 -44.00-144.00   91
 16  \w   -123.00 -33.00   1.00    5.00    -- -110.00  72.00 -36.00   90
 17  \w   -187.00 -97.00   1.00    5.00    -- -110.00 -15.00-108.00   90
 18  \w   -187.00 -96.00   1.00    5.00    -- -110.00 -44.00 144.00   91
 19  \w   -115.00 -25.00   1.00    5.00    -- -110.00  72.00-144.00   90
 20  \w   -187.00 -97.00   1.00    5.00    -- -110.00 -44.00-180.00   90
 21  \w   -187.00 -96.00   1.00    5.00    -- -110.00 -72.00-108.00   91
 22  \w   -187.00 -97.00   1.00    5.00    -- -110.00 -44.00 108.00   90
 23  \w   -187.00 -96.00   1.00    5.00    -- -110.00 -72.00-180.00   91
 24  \w   -115.00 -25.00   1.00    5.00    -- -110.00  72.00  72.00   90
 25  \w   -123.00 -33.00   1.00    5.00    -- -110.00  72.00-180.00   90
 26  \w   -187.00 -96.00   1.00    5.00    -- -110.00 -44.00  72.00   91
 27  \w   -200.00-110.00   1.00    5.00    -- -110.00 -15.00-180.00   90
 28  \w   -187.00 -97.00   1.00    5.00    -- -110.00 -15.00 108.00   90
 29  \w   -187.00 -97.00   1.00    5.00    -- -110.00 -72.00 -72.00   90
;
_diffrn_measurement_device       'AFC12 (Right): Kappa 3 circle'
_diffrn_measurement_device_type  'Rigaku XtaLab P200'
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_measurement_specimen_support Fiber
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0186990000
_diffrn_orient_matrix_UB_12      -0.0220150000
_diffrn_orient_matrix_UB_13      -0.1141379000
_diffrn_orient_matrix_UB_21      -0.1802688000
_diffrn_orient_matrix_UB_22      -0.0040490000
_diffrn_orient_matrix_UB_23      -0.0031491000
_diffrn_orient_matrix_UB_31      -0.0046357000
_diffrn_orient_matrix_UB_32      0.2380268000
_diffrn_orient_matrix_UB_33      -0.0104624000
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0262
_diffrn_reflns_av_unetI/netI     0.0150
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            11699
_diffrn_reflns_point_group_measured_fraction_full 0.876
_diffrn_reflns_point_group_measured_fraction_max 0.851
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.198
_diffrn_reflns_theta_min         3.286
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           30.0
_diffrn_source_power             1.2
_diffrn_source_target            Cu
_diffrn_source_type              'Rotating Anode'
_diffrn_source_voltage           40.0
_exptl_absorpt_coefficient_mu    0.532
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.46418
_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    1.174
_exptl_crystal_description       prism
_exptl_crystal_F_000             280
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.144
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details
;
 Flack x determined using 953 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.8(5)
_refine_ls_extinction_coef       0.098(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2735
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.0449
_refine_ls_R_factor_gt           0.0445
_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^)+(0.0930P)^2^+0.0190P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1310
_refine_ls_wR_factor_ref         0.1316
_reflns_Friedel_coverage         0.593
_reflns_Friedel_fraction_full    0.732
_reflns_Friedel_fraction_max     0.697
_reflns_number_gt                2647
_reflns_number_total             2735
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b02547_si_002.cif
_cod_data_source_block           p20161228a
_cod_database_code               4132241
_chemical_oxdiff_formula         C18H18N2
_shelx_estimated_absorpt_t_max   0.892
_shelx_estimated_absorpt_t_min   0.831
_reflns_odcompleteness_completeness 97.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     78.95
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B), C11(H11A,H11B), C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C14(H14), C15(H15), C16(H16), C17(H17),
 C18(H18)
;
_shelx_res_checksum              72614
_shelx_hkl_checksum              40373
_shelx_shelxl_version_number     2014/7
_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 1.526
_oxdiff_exptl_absorpt_empirical_full_min 0.604