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_4134104
_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         'C25 H22 Br N3'
_chemical_formula_sum            'C25 H22 Br N3'
_chemical_formula_weight         444.36
_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'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2018-12-13
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 106.018(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.7135(14)
_cell_length_b                   14.8409(15)
_cell_length_c                   12.0272(13)
_cell_measurement_reflns_used    9877
_cell_measurement_temperature    163(2)
_cell_measurement_theta_max      25.01
_cell_measurement_theta_min      2.55
_cell_volume                     2009.6(4)
_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  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      163(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0793
_diffrn_reflns_av_unetI/netI     0.0633
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            19063
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.050
_diffrn_reflns_theta_max         25.050
_diffrn_reflns_theta_min         2.233
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.062
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.5698
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.469
_exptl_crystal_description       plate
_exptl_crystal_F_000             912
_refine_diff_density_max         1.290
_refine_diff_density_min         -0.543
_refine_diff_density_rms         0.099
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         3550
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0543
_refine_ls_R_factor_gt           0.0481
_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^)+(0.0824P)^2^+1.0970P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1300
_refine_ls_wR_factor_ref         0.1363
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3099
_reflns_number_total             3550
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b12503_si_002.cif
_cod_data_source_block           1422_0m_a
_cod_database_code               4134104
_shelx_shelxl_version_number     2018/3
_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. Rigid bond restraints
 C9, C10
 with sigma for 1-2 distances of 0.0001 and sigma for 1-3 distances of 0.0001
3.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C6(H6A,H6B), C4(H4A,H4B), C5(H5A,H5B)
3.b Aromatic/amide H refined with riding coordinates:
 C18(H18), C24(H24), C21(H21), C23(H23), C16(H16), C9(H9), C12(H12), C10(H10),
 C11(H11), C15(H15), C22(H22)
3.c Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C)
;
_shelx_res_checksum              10437
_shelx_hkl_checksum              43697
_olex2_submission_special_instructions 'No special instructions were received'