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_4134105
_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_absolute_configuration ad
_chemical_formula_moiety         'C27 H25 Br N2 O'
_chemical_formula_sum            'C27 H25 Br N2 O'
_chemical_formula_weight         473.40
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                91.478(7)
_cell_angle_beta                 97.316(7)
_cell_angle_gamma                111.443(8)
_cell_formula_units_Z            1
_cell_length_a                   6.1625(5)
_cell_length_b                   8.0217(7)
_cell_length_c                   12.3804(11)
_cell_measurement_reflns_used    3765
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      24.888
_cell_measurement_theta_min      2.843
_cell_volume                     563.27(9)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'RIGAKU Xtalab Pilatus200'
_diffrn_measurement_method       'phi and omega scan'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0451
_diffrn_reflns_av_unetI/netI     0.0571
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8735
_diffrn_reflns_point_group_measured_fraction_full 0.959
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full        25.081
_diffrn_reflns_theta_max         25.081
_diffrn_reflns_theta_min         2.736
_exptl_absorpt_coefficient_mu    1.846
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.789
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_description       needle
_exptl_crystal_F_000             244
_exptl_crystal_size_max          0.430
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.150
_refine_diff_density_max         1.116
_refine_diff_density_min         -0.645
_refine_diff_density_rms         0.099
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   -0.037(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         3846
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0639
_refine_ls_R_factor_gt           0.0545
_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^)+(0.0993P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1365
_refine_ls_wR_factor_ref         0.1418
_reflns_Friedel_coverage         0.924
_reflns_Friedel_fraction_full    0.921
_reflns_Friedel_fraction_max     0.921
_reflns_number_gt                3288
_reflns_number_total             3846
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b12503_si_004.cif
_cod_data_source_block           shelx
_cod_database_code               4134105
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.504
_shelx_estimated_absorpt_t_max   0.769
_shelx_res_checksum              34068
_shelx_hkl_checksum              28792