Lewis Base/Copper Cooperatively Catalyzed Asymmetric α-Amination of Esters with Diaziridinone.
Song, Jin; Zhang, Zi-Jing; Chen, Shu-Sen; Fan, Tao; Gong, Liu-Zhu; Journal of the American Chemical Society 140 (2018) 3177–3180; doi:10.1021/jacs.7b12628

data_4131899
_publ_section_title
;
 Lewis Base/Copper Cooperatively Catalyzed Asymmetric \a-Amination of
 Esters with Diaziridinone.
;
_journal_issue                   9
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              3177
_journal_page_last               3180
_journal_paper_doi               10.1021/jacs.7b12628
_journal_volume                  140
_journal_year                    2018
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C17 H24 N2 O2'
_chemical_formula_sum            'C17 H24 N2 O2'
_chemical_formula_weight         288.38
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2017-08-14
_audit_creation_method
;
Olex2 1.2
(compiled 2017.07.20 svn.r3457 for OlexSys, GUI svn.r5375)
;
_cell_angle_alpha                90
_cell_angle_beta                 112.9520(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.1758(3)
_cell_length_b                   10.3730(3)
_cell_length_c                   14.1803(4)
_cell_measurement_reflns_used    6666
_cell_measurement_temperature    198(2)
_cell_measurement_theta_max      69.871
_cell_measurement_theta_min      3.385
_cell_volume                     1649.18(8)
_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  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      198.26
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0428
_diffrn_reflns_av_unetI/netI     0.0469
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            17507
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.379
_diffrn_reflns_theta_min         3.385
_exptl_absorpt_coefficient_mu    0.606
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.5837
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1287 before and 0.0718 after correction. The Ratio of minimum to maximum transmission is 0.7749. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.161
_exptl_crystal_description       block
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.280
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details
;
 Flack x determined using 1998 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.19(14)
_refine_ls_extinction_coef       0.011(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     392
_refine_ls_number_reflns         6172
_refine_ls_number_restraints     19
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0779
_refine_ls_R_factor_gt           0.0689
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1182P)^2^+0.2320P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1795
_refine_ls_wR_factor_ref         0.1908
_reflns_Friedel_coverage         0.862
_reflns_Friedel_fraction_full    0.970
_reflns_Friedel_fraction_max     0.964
_reflns_number_gt                5314
_reflns_number_total             6172
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja7b12628_si_002.cif
_cod_data_source_block           cu_d8v17253_0m
_cod_database_code               4131899
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.970
_shelx_estimated_absorpt_t_min   0.915
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
C10 \\sim C12 \\sim C11 \\sim C13: within 2A with sigma of 0.005 and sigma for
terminal atoms of 0.01
3.a Ternary CH refined with riding coordinates:
 C1(H1), C1A(H1A)
3.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C9(H9), C5A(H5A), C6A(H6A), C7A(H7A),
 C8A(H8A), C9A(H9A)
3.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C15(H15A,H15B,
 H15C), C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C11A(H11D,H11E,H11F),
 C12A(H12D,H12E,H12F), C13A(H13D,H13E,H13F), C15A(H15D,H15E,H15F), C16A(H16D,
 H16E,H16F), C17A(H17D,H17E,H17F)
;
_shelx_res_checksum              33722
_shelx_hkl_checksum              9120
_olex2_submission_special_instructions 'No special instructions were received'