Construction of All-Carbon Quaternary Stereocenters by Scandium-Catalyzed Intramolecular C-H Alkylation of Imidazoles with 1,1-Disubstituted Alkenes.
Lou, Shao-Jie; Mo, Zhenbo; Nishiura, Masayoshi; Hou, Zhaomin; Journal of the American Chemical Society 142 (2020) 1200–1205; doi:10.1021/jacs.9b12503

data_4134106
_publ_section_title
;
 Construction of All-Carbon Quaternary Stereocenters by Scandium-Catalyzed
 Intramolecular C-H Alkylation of Imidazoles with 1,1-Disubstituted
 Alkenes.
;
_journal_issue                   3
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              1200
_journal_page_last               1205
_journal_paper_doi               10.1021/jacs.9b12503
_journal_volume                  142
_journal_year                    2020
_chemical_formula_moiety         'C23 H24 N2'
_chemical_formula_sum            'C23 H24 N2'
_chemical_formula_weight         328.46
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_Int_Tables_number      14
_audit_creation_date             2019-01-08
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 97.440(5)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.9079(14)
_cell_length_b                   17.101(3)
_cell_length_c                   21.218(4)
_cell_measurement_reflns_used    9912
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      24.89
_cell_measurement_theta_min      2.27
_cell_volume                     3564.8(10)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_measured_fraction_theta_full 0.9962
_diffrn_measured_fraction_theta_max 0.9962
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1198
_diffrn_reflns_av_unetI/netI     0.0646
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            59304
_diffrn_reflns_theta_full        25.1214
_diffrn_reflns_theta_max         25.12
_diffrn_reflns_theta_min         1.53
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.5750
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.2240
_exptl_crystal_description       plate
_exptl_crystal_F_000             1408.4998
_refine_diff_density_max         1.2897
_refine_diff_density_min         -0.5880
_refine_diff_density_rms         0.0927
_refine_ls_d_res_high            0.8371
_refine_ls_d_res_low             13.2701
_refine_ls_goodness_of_fit_ref   1.1796
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    82
_refine_ls_number_parameters     453
_refine_ls_number_reflns         6348
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.1796
_refine_ls_R_factor_all          0.1241
_refine_ls_R_factor_gt           0.0926
_refine_ls_shift/su_max          4.1195
_refine_ls_shift/su_mean         0.6572
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1218P)^2^+6.1903P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2525
_refine_ls_wR_factor_ref         0.2996
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              11
_reflns_limit_h_min              -11
_reflns_limit_k_max              20
_reflns_limit_k_min              0
_reflns_limit_l_max              25
_reflns_limit_l_min              0
_reflns_number_gt                4538
_reflns_number_total             6348
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            ja9b12503_si_003.cif
_cod_data_source_block           1444_0ma_a
_cod_original_cell_volume        3564.7(10)
_cod_database_code               4134106
_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:
 C00W(H00W), C00Z(H00Z)
2.b Secondary CH2 refined with riding coordinates:
 C00V(H00a,H00c), C013(H01l,H01m), C014(H01a,H01b), C016(H01c,H01d), C018(H01n,
 H01o), C019(H01h,H01i), C01B(H01j,H01k), C01C(H01s,H01t), C01D(H01u,H01v),
 C01E(H01w,H01x)
2.c Aromatic/amide H refined with riding coordinates:
 C00B(H00B), C00D(H00D), C00F(H00F), C00G(H00G), C00H(H00H), C00I(H00I),
 C00J(H00J), C00L(H00L), C00M(H00M), C00N(H00N), C00O(H00O), C00P(H00P),
 C00Q(H00Q), C00R(H00R), C00S(H00S), C00U(H00U), C00X(H00X), C00Y(H00Y),
 C010(H010), C012(H012)
2.d Idealised Me refined as rotating group:
 C017(H01e,H01f,H01g), C01A(H01p,H01q,H01r)
;
_olex2_submission_special_instructions 'No special instructions were received'