Bisguanidinium-Catalyzed Epoxidation of Allylic and Homoallylic Amines under Phase Transfer Conditions
Chin, Kek Foo; Ye, Xinyi; Li, Yongxin; Lee, Richmond; Kabylda, Adil M.; Leow, Dasheng; Zhang, Xin; Xia Ang, Esther Cai; Tan, Choon-Hong; ACS Catalysis  (2020) 2684–; doi:10.1021/acscatal.9b04862

data_4517394
_publ_section_title
;
 Bisguanidinium-Catalyzed Epoxidation of Allylic and Homoallylic Amines
 under Phase Transfer Conditions
;
_journal_name_full               'ACS Catalysis'
_journal_page_first              2684
_journal_paper_doi               10.1021/acscatal.9b04862
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_sum            'C24 H25 N O3 S'
_chemical_formula_weight         407.51
_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
_cell_angle_alpha                90
_cell_angle_beta                 107.843(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.1788(11)
_cell_length_b                   8.3217(6)
_cell_length_c                   17.7545(16)
_cell_measurement_reflns_used    9785
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      30.6412
_cell_measurement_theta_min      2.4102
_cell_volume                     1994.1(3)
_computing_cell_refinement       'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_data_collection       'APEX3 (Bruker AXS Inc., 2016)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_molecular_graphics    'XP (Bruker AXS Inc., 2016)'
_computing_publication_material  'APEX3 (Bruker AXS Inc., 2016)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'XS, VERSION 2013/1'
_diffrn_ambient_temperature      100.(2)
_diffrn_detector_area_resol_mean 7.4074
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Photon II CPADs detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  'Multilayer Mirror'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1237
_diffrn_reflns_av_unetI/netI     0.1346
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            54841
_diffrn_reflns_theta_full        31.06
_diffrn_reflns_theta_max         31.06
_diffrn_reflns_theta_min         2.42
_diffrn_source                   'Incoatec microfocus source'
_diffrn_source_type              'Bruker D8 Quest'
_exptl_absorpt_coefficient_mu    0.189
_exptl_absorpt_correction_T_max  0.96
_exptl_absorpt_correction_T_min  0.79
_exptl_absorpt_correction_type   'Numerical Mu From Formula'
_exptl_absorpt_process_details
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.236
_exptl_crystal_size_mid          0.233
_exptl_crystal_size_min          0.224
_refine_diff_density_max         0.410
_refine_diff_density_min         -0.437
_refine_ls_abs_structure_details
;

Flack x determined using 2337 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.08(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     525
_refine_ls_number_reflns         12594
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.1504
_refine_ls_R_factor_gt           0.0700
_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^)+(0.0329P)^2^+0.8850P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1124
_refine_ls_wR_factor_ref         0.1414
_reflns_number_gt                7543
_reflns_number_total             12594
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs9b04862_si_002.cif
_cod_data_source_block           tch109m
_cod_database_code               4517394
_shelx_res_checksum              93078
_shelx_hkl_checksum              39464