Enantioselective Vinylogous Conia-Ene Reaction Catalyzed by a Disilver(I)/Bisdiamine Complex
Zou, Chuncheng; Yang, Lei; Zhang, Lei; Liu, Chengyu; Ma, Yueyue; Song, Gonghua; Liu, Zhen; Cheng, Ruihua; Ye, Jinxing; ACS Catalysis  (2021) 6865–6871; doi:10.1021/acscatal.1c01033

data_4518765
_publ_section_title
;
 Enantioselective Vinylogous Conia-Ene Reaction Catalyzed by a
 Disilver(I)/Bisdiamine Complex
;
_journal_name_full               'ACS Catalysis'
_journal_page_first              6865
_journal_page_last               6871
_journal_paper_doi               10.1021/acscatal.1c01033
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C12 H26 Ag N2, C2 H F6 N O4 S2'
_chemical_formula_sum            'C14 H27 Ag F6 N3 O4 S2'
_chemical_formula_weight         587.37
_space_group_crystal_system      tetragonal
_space_group_IT_number           96
_space_group_name_Hall           'P 4nw 2abw'
_space_group_name_H-M_alt        'P 43 21 2'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2021-05-17
_audit_creation_method
; 
Olex2 1.2 
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) 
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   18.9333(5)
_cell_length_b                   18.9333(5)
_cell_length_c                   13.1408(5)
_cell_measurement_reflns_used    9981
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      52.052
_cell_measurement_theta_min      4.011
_cell_volume                     4710.6(3)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       'Bruker APEX2'
_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    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      193.0
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.995
_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  0.0319
_diffrn_reflns_av_unetI/netI     0.0254
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            23616
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.993
_diffrn_reflns_theta_min         2.405
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.104
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6143
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.656
_exptl_crystal_description       block
_exptl_crystal_F_000             2376
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         2.158
_refine_diff_density_min         -0.590
_refine_diff_density_rms         0.129
_refine_ls_abs_structure_details
; 
 Flack x determined using 1560 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.013(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     339
_refine_ls_number_reflns         4628
_refine_ls_number_restraints     96
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.0744
_refine_ls_R_factor_gt           0.0655
_refine_ls_shift/su_max          0.014
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1419P)^2^+5.6732P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1931
_refine_ls_wR_factor_ref         0.2065
_reflns_Friedel_coverage         0.741
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                4005
_reflns_number_total             4628
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs1c01033_si_002.cif
_cod_data_source_block           CCDC2027416
_cod_database_code               4518765
_shelxl_version_number           2013-4
_shelx_estimated_absorpt_t_max   0.879
_shelx_estimated_absorpt_t_min   0.826
_olex2_refinement_description
; 
1. Fixed Uiso 
 At 1.2 times of: 
  All C(H) groups, All C(H,H) groups, All C(H,H,H) groups, All C(H,H,H,H) 
  groups, All N(H) groups, All N(H,H) groups 
2. Restrained distances 
 C7'-C8' = C8'-C9' = C9'-C10' = C10'-C11' = C11'-C12' = C12'-C7' 
 1.55 with sigma of 0.02 
 C7-C8 = C8-C9 = C9-C10 = C10-C11 = C11-C12 = C12-C7 
 1.55 with sigma of 0.02 
3. Uiso/Uaniso restraints and constraints 
F1 \\sim F2 \\sim F3 \\sim F4 \\sim F5 \\sim F6: within 2A with sigma of 0.004 
and sigma for terminal atoms of 0.008 
C4 \\sim C5 \\sim C6: within 2A with sigma of 0.003 and sigma for terminal 
atoms of 0.006 
Uanis(C7) \\sim Ueq, Uanis(C8) \\sim Ueq, Uanis(C9) \\sim Ueq, Uanis(C10) \\sim 
Ueq, Uanis(C11) \\sim Ueq, Uanis(C12) \\sim Ueq: with sigma of 0.01 and sigma 
for terminal atoms of 0.02 
Uanis(C7') \\sim Ueq, Uanis(C8') \\sim Ueq, Uanis(C9') \\sim Ueq, Uanis(C10') 
\\sim Ueq, Uanis(C11') \\sim Ueq, Uanis(C12') \\sim Ueq: with sigma of 0.01 and 
sigma for terminal atoms of 0.02 
Uanis(N1) \\sim Ueq, Uanis(N1') \\sim Ueq: with sigma of 0.01 and sigma for 
terminal atoms of 0.02 
4. Others 
 Fixed Sof: N1(0.6) H1(0.6) N1'(0.4) H1'(0.4) H1AA(0.6) H1AB(0.6) H1BC(0.4) 
 H1BD(0.4) C7(0.7) H7(0.7) C8(0.5) H8A(0.5) H8B(0.5) C9(0.5) H9A(0.5) H9B(0.5) 
 C10(0.5) H10A(0.5) H10B(0.5) C11(0.5) H11A(0.5) H11B(0.5) C12(0.5) H12A(0.5) 
 H12B(0.5) C7'(0.3) H7'(0.3) C8'(0.5) H8'A(0.5) H8'B(0.5) C9'(0.5) H9'A(0.5) 
 H9'B(0.5) C10'(0.5) H10C(0.5) H10D(0.5) C11'(0.5) H11C(0.5) H11D(0.5) 
 C12'(0.5) H12C(0.5) H12D(0.5) 
5.a Riding coordinates: 
 N1(H1), N1'(H1'), N2(H2A,H2B), N3(H3), C1(H1AA,H1AB,H1BC,H1BD), C4(H4A,H4B, 
 H4C), C6(H6A,H6B,H6C) 
5.b Ternary CH refined with riding coordinates: 
 C2(H2), C7(H7), C7'(H7') 
5.c Secondary CH2 refined with riding coordinates: 
 C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B), C12(H12A,H12B), 
 C8'(H8'A,H8'B), C9'(H9'A,H9'B), C10'(H10C,H10D), C11'(H11C,H11D), C12'(H12C, 
 H12D) 
5.d Idealised Me refined as rotating group: 
 C5(H5A,H5B,H5C) 
;
_shelx_res_checksum              59863
_shelx_hkl_checksum              80302
_shelx_fab_checksum              20847
_olex2_submission_special_instructions 'No special instructions were received'