Catalytic Asymmetric Chemodivergent C2 Alkylation and [3 + 2]-Cycloaddition of 3-Methylindoles with Aziridines
Xu, Yali; Chang, Fenzhen; Cao, Weidi; Liu, Xiaohua; Feng, Xiaoming; ACS Catalysis 8 (2018) 10261–; doi:10.1021/acscatal.8b02880

data_4515761
_publ_section_title
;
 Catalytic Asymmetric Chemodivergent C2 Alkylation and [3 +
 2]-Cycloaddition of 3-Methylindoles with Aziridines
;
_journal_issue                   11
_journal_name_full               'ACS Catalysis'
_journal_page_first              10261
_journal_paper_doi               10.1021/acscatal.8b02880
_journal_volume                  8
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_sum            'C42 H60 Br2 F9 N4 O16 S3 Tm'
_chemical_formula_weight         1472.87
_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
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 93.281(12)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.458(3)
_cell_length_b                   25.399(8)
_cell_length_c                   11.670(4)
_cell_measurement_reflns_used    7005
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      27.17
_cell_measurement_theta_min      2.38
_cell_volume                     2798.8(16)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_diffrn_ambient_temperature      170(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'BRUKER D8 VENTURE PHOTON II'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0819
_diffrn_reflns_av_unetI/netI     0.1208
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            28060
_diffrn_reflns_point_group_measured_fraction_full 0.877
_diffrn_reflns_point_group_measured_fraction_max 0.830
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.465
_diffrn_reflns_theta_min         2.688
_exptl_absorpt_coefficient_mu    3.221
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.5489
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_density_diffrn    1.748
_exptl_crystal_description       plate
_exptl_crystal_F_000             1472
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.010
_refine_diff_density_max         2.393
_refine_diff_density_min         -2.171
_refine_diff_density_rms         0.188
_refine_ls_abs_structure_details
;
 Flack x determined using 2371 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.070(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     773
_refine_ls_number_reflns         11725
_refine_ls_number_restraints     2399
_refine_ls_restrained_S_all      0.982
_refine_ls_R_factor_all          0.1180
_refine_ls_R_factor_gt           0.0778
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1146P)^2^+5.3539P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1882
_refine_ls_wR_factor_ref         0.2152
_reflns_Friedel_coverage         0.649
_reflns_Friedel_fraction_full    0.749
_reflns_Friedel_fraction_max     0.668
_reflns_number_gt                8097
_reflns_number_total             11725
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs8b02880_si_004.cif
_cod_data_source_block           mo_20180511xyl_tmpiet2_0m
_cod_original_cell_volume        2798.7(15)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4515761
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.739
_shelx_estimated_absorpt_t_max   0.968
_shelx_res_checksum              34567
_shelx_hkl_checksum              43263