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_4517395
_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            'C100 H138 N8 O13 W2'
_chemical_formula_weight         2027.88
_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
_atom_sites_solution_primary     dual
_cell_angle_alpha                102.5903(17)
_cell_angle_beta                 97.3713(16)
_cell_angle_gamma                101.976(2)
_cell_formula_units_Z            1
_cell_length_a                   10.9657(8)
_cell_length_b                   14.7551(12)
_cell_length_c                   16.1650(12)
_cell_measurement_reflns_used    9512
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      23.5217
_cell_measurement_theta_min      2.5004
_cell_volume                     2455.5(3)
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_collection       'APEX3 (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_molecular_graphics    'XP (Bruker AXS Inc., 2017)'
_computing_publication_material  'APEX3 (Bruker AXS Inc., 2017)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'XT, VERSION 2014/5'
_diffrn_ambient_temperature      100.(2)
_diffrn_detector_area_resol_mean 7.4074
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0999
_diffrn_reflns_av_unetI/netI     0.0789
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            10058
_diffrn_reflns_theta_full        26.39
_diffrn_reflns_theta_max         26.39
_diffrn_reflns_theta_min         2.19
_diffrn_source                   'Incoatec microfocus source'
_diffrn_source_type              'Bruker D8 Quest'
_exptl_absorpt_coefficient_mu    2.403
_exptl_absorpt_correction_T_max  0.95
_exptl_absorpt_correction_T_min  0.71
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'TWINABS - Bruker AXS scaling for twinned crystals - Version 2012/1'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1046
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.020
_refine_diff_density_max         3.218
_refine_diff_density_min         -1.440
_refine_ls_abs_structure_details
;

No quotients, so Flack parameter determined by classical intensity fit
;
_refine_ls_abs_structure_Flack   0.064(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1207
_refine_ls_number_reflns         10058
_refine_ls_number_restraints     1502
_refine_ls_restrained_S_all      0.992
_refine_ls_R_factor_all          0.0800
_refine_ls_R_factor_gt           0.0611
_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^)+(0.0952P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1464
_refine_ls_wR_factor_ref         0.1567
_reflns_number_gt                7880
_reflns_number_total             10058
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs9b04862_si_003.cif
_cod_data_source_block           tch138m_0m_4
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-Scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_database_code               4517395
_shelx_res_checksum              3661
_shelx_hkl_checksum              1889