#------------------------------------------------------------------------------
#$Date: 2019-11-03 11:01:44 +0200 (Sun, 03 Nov 2019) $
#$Revision: 221211 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/12/80/4128080.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4128080
loop_
_publ_author_name
'Kang, Zhenghui'
'Wang, Yongheng'
'Zhang, Dan'
'Wu, Ruibo'
'Xu, Xinfang'
'Hu, Wenhao'
_publ_section_title
;
 Asymmetric Counter-Anion-Directed Aminomethylation: Synthesis of Chiral
 β-Amino Acids via Trapping of an Enol Intermediate.
;
_journal_issue                   4
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              1473
_journal_page_last               1478
_journal_paper_doi               10.1021/jacs.8b12832
_journal_volume                  141
_journal_year                    2019
_chemical_formula_moiety         'C15 H17 Ag O11'
_chemical_formula_sum            'C15 H17 Ag O11'
_chemical_formula_weight         481.15
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2018-06-14
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                107.990(4)
_cell_angle_beta                 100.432(3)
_cell_angle_gamma                104.927(4)
_cell_formula_units_Z            2
_cell_length_a                   8.8042(3)
_cell_length_b                   10.5315(4)
_cell_length_c                   10.8818(4)
_cell_measurement_reflns_used    5934
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      73.8500
_cell_measurement_theta_min      4.4390
_cell_volume                     889.20(7)
_computing_cell_refinement       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω    -30.00   1.00   1.00    1.00    --    0.00  79.00-168.00   31
  2  ω      7.00  48.00   1.00    1.00    --    0.00  79.00-168.00   41
  3  ω     79.00 127.00   1.00    1.00    --   95.80 -79.00  66.00   48
  4  ω     83.00 177.00   1.00    1.00    --   95.80  79.00-168.00   94
  5  ω    -88.00  17.00   1.00    1.00    --    0.00 -38.00-180.00  105
  6  ω    -89.00 -19.00   1.00    1.00    --    0.00 -19.00 120.00   70
  7  ω     11.00  37.00   1.00    1.00    --    0.00  38.00  60.00   26
  8  ω    -48.00  -1.00   1.00    1.00    --    0.00 -79.00  66.00   47
  9  ω      6.00  67.00   1.00    1.00    --   95.80 -82.00 -30.00   61
 10  ω     80.00 128.00   1.00    1.00    --   95.80 -82.00 -30.00   48
 11  ω      6.00  56.00   1.00    1.00    --   95.80 -15.00-120.00   50
 12  ω     91.00 117.00   1.00    1.00    --   95.80 -82.00-180.00   26
 13  ω      7.00 128.00   1.00    1.00    --   95.80 -82.00 150.00  121
 14  ω    109.00 135.00   1.00    1.00    --   95.80  30.00-180.00   26
 15  ω     13.00 116.00   1.00    1.00    --   95.80 -61.00   0.00  103
 16  ω      8.00  34.00   1.00    1.00    --   95.80 -82.00-120.00   26
 17  ω     38.00  69.00   1.00    1.00    --   95.80 -82.00-120.00   31
 18  ω     76.00 126.00   1.00    1.00    --   95.80 -82.00-120.00   50
 19  ω     76.00 106.00   1.00    1.00    --   95.80  61.00  30.00   30
 20  ω      7.00  69.00   1.00    1.00    --   95.80 -82.00-180.00   62
 21  ω     75.00 184.00   1.00    1.00    --   95.80  45.00 150.00  109
 22  ω    140.00 166.00   1.00    1.00    --   95.80  61.00  30.00   26
 23  ω     83.00 181.00   1.00    1.00    --   95.80  77.00-150.00   98
 24  ω     91.00 116.00   1.00    1.00    --   95.80 -77.00 -90.00   25
 25  ω     59.00  85.00   1.00    1.00    --   95.80 -15.00-120.00   26
 26  ω     96.00 122.00   1.00    1.00    --   95.80 -82.00  30.00   26
 27  ω     26.00  67.00   1.00    1.00    --   95.80 -45.00-120.00   41
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0968115000
_diffrn_orient_matrix_UB_12      0.0637179000
_diffrn_orient_matrix_UB_13      -0.0825432000
_diffrn_orient_matrix_UB_21      0.1030099000
_diffrn_orient_matrix_UB_22      0.1500624000
_diffrn_orient_matrix_UB_23      0.1027663000
_diffrn_orient_matrix_UB_31      0.1252156000
_diffrn_orient_matrix_UB_32      0.0083318000
_diffrn_orient_matrix_UB_33      -0.0819722000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.1218
_diffrn_reflns_av_unetI/netI     0.0936
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            8630
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.079
_diffrn_reflns_theta_max         67.079
_diffrn_reflns_theta_min         4.455
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    9.650
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.23381
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.32a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.797
_exptl_crystal_description       block
_exptl_crystal_F_000             484
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.18
_refine_diff_density_max         1.771
_refine_diff_density_min         -1.752
_refine_diff_density_rms         0.189
_refine_ls_extinction_coef       0.0031(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     251
_refine_ls_number_reflns         3144
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.0735
_refine_ls_R_factor_gt           0.0691
_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/[σ²(Fo²)+(0.1368P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1793
_refine_ls_wR_factor_ref         0.1836
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2822
_reflns_number_total             3144
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja8b12832_si_003.cif
_cod_data_source_block           exp_377
_cod_original_cell_volume        889.19(6)
_cod_database_code               4128080
_shelx_shelxl_version_number     2016/6
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_reflns_odcompleteness_completeness 99.21
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2.a Rotating group:
 O11(H11A,H11B)
2.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C9(H9A,H9B,H9C), C11(H11C,H11D,H11E), C13(H13A,H13B,H13C),
 C15(H15A,H15B,H15C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 6.200
_oxdiff_exptl_absorpt_empirical_full_min 0.242
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
Ag1 Ag 0.91160(5) 0.41312(5) 0.29113(4) 0.0489(3) Uani 1 1 d .
O1 O 0.9233(6) 0.2711(5) 0.4693(5) 0.0561(11) Uani 1 1 d .
O2 O 0.6861(5) 0.1357(4) 0.4742(4) 0.0469(10) Uani 1 1 d .
O3 O 0.9074(6) 0.1608(4) 0.7381(5) 0.0501(10) Uani 1 1 d .
O4 O 0.7181(6) 0.1568(4) 0.8484(5) 0.0519(11) Uani 1 1 d .
O5 O 0.8145(7) 0.4295(5) 1.0604(4) 0.0595(12) Uani 1 1 d .
O6 O 0.7115(6) 0.5939(5) 1.0362(4) 0.0545(11) Uani 1 1 d .
O7 O 0.5828(5) 0.6805(4) 0.8254(4) 0.0440(9) Uani 1 1 d .
O8 O 0.8497(5) 0.8036(4) 0.8892(4) 0.0440(9) Uani 1 1 d .
O9 O 0.6978(6) 0.6509(4) 0.5764(4) 0.0451(9) Uani 1 1 d .
O10 O 0.7388(5) 0.4743(4) 0.4242(4) 0.0421(9) Uani 1 1 d .
O11 O 0.8340(6) 0.1798(5) 0.1270(4) 0.0491(10) Uani 1 1 d .
H11A H 0.776473 0.117946 0.153082 0.074 Uiso 1 1 d GR
H11B H 0.920238 0.155159 0.120885 0.074 Uiso 1 1 d GR
C1 C 0.7833(6) 0.4929(5) 0.6540(5) 0.0312(10) Uani 1 1 d .
C2 C 0.7606(6) 0.5512(5) 0.7817(5) 0.0304(10) Uani 1 1 d .
C3 C 0.7672(6) 0.4584(5) 0.8495(5) 0.0309(10) Uani 1 1 d .
C4 C 0.7921(6) 0.3384(5) 0.7619(5) 0.0323(10) Uani 1 1 d .
C5 C 0.8031(6) 0.3586(5) 0.6424(5) 0.0336(11) Uani 1 1 d .
C6 C 0.8142(6) 0.2552(5) 0.5211(5) 0.0351(11) Uani 1 1 d .
C7 C 0.6867(11) 0.0224(7) 0.3578(8) 0.067(2) Uani 1 1 d .
H7A H 0.696185 0.055881 0.285976 0.100 Uiso 1 1 calc GR
H7B H 0.586501 -0.055833 0.329138 0.100 Uiso 1 1 calc GR
H7C H 0.777993 -0.008028 0.381275 0.100 Uiso 1 1 calc GR
C8 C 0.8006(6) 0.2111(5) 0.7889(6) 0.0377(12) Uani 1 1 d .
C9 C 0.9250(11) 0.0345(8) 0.7589(9) 0.069(2) Uani 1 1 d .
H9A H 0.833864 -0.047045 0.697923 0.104 Uiso 1 1 calc GR
H9B H 0.927615 0.044223 0.849991 0.104 Uiso 1 1 calc GR
H9C H 1.025085 0.023085 0.742414 0.104 Uiso 1 1 calc GR
C10 C 0.7679(6) 0.4892(5) 0.9907(5) 0.0346(11) Uani 1 1 d .
C11 C 0.6999(9) 0.6310(7) 1.1723(6) 0.0545(16) Uani 1 1 d .
H11C H 0.631729 0.549367 1.181864 0.082 Uiso 1 1 calc GR
H11D H 0.652811 0.705052 1.192147 0.082 Uiso 1 1 calc GR
H11E H 0.807324 0.663234 1.233663 0.082 Uiso 1 1 calc GR
C12 C 0.7377(6) 0.6923(5) 0.8385(5) 0.0336(11) Uani 1 1 d .
C13 C 0.5496(10) 0.8108(8) 0.8830(11) 0.076(2) Uani 1 1 d .
H13A H 0.570149 0.867517 0.829811 0.113 Uiso 1 1 calc GR
H13B H 0.619670 0.862241 0.973510 0.113 Uiso 1 1 calc GR
H13C H 0.437140 0.788746 0.883940 0.113 Uiso 1 1 calc GR
C14 C 0.7424(6) 0.5357(5) 0.5397(5) 0.0323(10) Uani 1 1 d .
C15 C 0.6494(8) 0.7037(7) 0.4736(6) 0.0511(15) Uani 1 1 d .
H15A H 0.567702 0.627811 0.397439 0.077 Uiso 1 1 calc GR
H15B H 0.743140 0.741403 0.446197 0.077 Uiso 1 1 calc GR
H15C H 0.605065 0.777032 0.508680 0.077 Uiso 1 1 calc GR
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ag Ag 0.1306 4.2820 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
O10 Ag1 O5 109.85(15) . 1_554
O10 Ag1 O11 120.36(15) . .
O10 Ag1 C1 129.50(14) . 2_766
O11 Ag1 O5 73.56(15) . 1_554
O11 Ag1 C1 104.78(16) . 2_766
C1 Ag1 O5 103.28(16) 2_766 1_554
C6 O2 C7 116.3(5) . .
C8 O3 C9 116.5(5) . .
C10 O5 Ag1 152.1(4) . 1_556
C10 O6 C11 117.3(5) . .
C12 O7 C13 116.3(5) . .
C14 O9 C15 117.4(4) . .
C14 O10 Ag1 141.4(3) . .
Ag1 O11 H11A 110.7 . .
Ag1 O11 H11B 110.2 . .
H11A O11 H11B 103.5 . .
C2 C1 Ag1 100.9(3) . 2_766
C2 C1 C5 107.1(4) . .
C2 C1 C14 125.9(5) . .
C5 C1 Ag1 85.7(3) . 2_766
C5 C1 C14 124.3(5) . .
C14 C1 Ag1 98.6(3) . 2_766
C1 C2 C12 125.7(4) . .
C3 C2 C1 109.1(4) . .
C3 C2 C12 125.1(4) . .
C2 C3 C4 107.5(4) . .
C2 C3 C10 125.3(5) . .
C4 C3 C10 126.9(4) . .
C3 C4 C8 126.5(5) . .
C5 C4 C3 108.6(4) . .
C5 C4 C8 124.9(5) . .
C1 C5 C6 125.7(4) . .
C4 C5 C1 107.7(5) . .
C4 C5 C6 126.2(4) . .
O1 C6 O2 122.7(5) . .
O1 C6 C5 126.2(5) . .
O2 C6 C5 111.1(4) . .
O2 C7 H7A 109.5 . .
O2 C7 H7B 109.5 . .
O2 C7 H7C 109.5 . .
H7A C7 H7B 109.5 . .
H7A C7 H7C 109.5 . .
H7B C7 H7C 109.5 . .
O3 C8 C4 112.0(4) . .
O4 C8 O3 123.3(5) . .
O4 C8 C4 124.7(6) . .
O3 C9 H9A 109.5 . .
O3 C9 H9B 109.5 . .
O3 C9 H9C 109.5 . .
H9A C9 H9B 109.5 . .
H9A C9 H9C 109.5 . .
H9B C9 H9C 109.5 . .
O5 C10 O6 122.2(5) . .
O5 C10 C3 126.0(5) . .
O6 C10 C3 111.8(4) . .
O6 C11 H11C 109.5 . .
O6 C11 H11D 109.5 . .
O6 C11 H11E 109.5 . .
H11C C11 H11D 109.5 . .
H11C C11 H11E 109.5 . .
H11D C11 H11E 109.5 . .
O7 C12 C2 112.4(4) . .
O8 C12 O7 124.2(5) . .
O8 C12 C2 123.4(5) . .
O7 C13 H13A 109.5 . .
O7 C13 H13B 109.5 . .
O7 C13 H13C 109.5 . .
H13A C13 H13B 109.5 . .
H13A C13 H13C 109.5 . .
H13B C13 H13C 109.5 . .
O9 C14 C1 110.8(4) . .
O10 C14 O9 122.3(4) . .
O10 C14 C1 126.8(5) . .
O9 C15 H15A 109.5 . .
O9 C15 H15B 109.5 . .
O9 C15 H15C 109.5 . .
H15A C15 H15B 109.5 . .
H15A C15 H15C 109.5 . .
H15B C15 H15C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ag1 O5 2.575(4) 1_554
Ag1 O10 2.357(4) .
Ag1 O11 2.383(5) .
Ag1 C1 2.497(5) 2_766
O1 C6 1.199(7) .
O2 C6 1.334(6) .
O2 C7 1.449(8) .
O3 C8 1.317(7) .
O3 C9 1.458(7) .
O4 C8 1.207(7) .
O5 C10 1.206(6) .
O6 C10 1.320(7) .
O6 C11 1.441(7) .
O7 C12 1.314(7) .
O7 C13 1.449(8) .
O8 C12 1.208(6) .
O9 C14 1.337(7) .
O9 C15 1.441(6) .
O10 C14 1.213(6) .
O11 H11A 0.8707 .
O11 H11B 0.8701 .
C1 C2 1.409(7) .
C1 C5 1.439(7) .
C1 C14 1.465(6) .
C2 C3 1.400(6) .
C2 C12 1.505(7) .
C3 C4 1.425(7) .
C3 C10 1.467(7) .
C4 C5 1.397(7) .
C4 C8 1.475(6) .
C5 C6 1.467(7) .
C7 H7A 0.9600 .
C7 H7B 0.9600 .
C7 H7C 0.9600 .
C9 H9A 0.9600 .
C9 H9B 0.9600 .
C9 H9C 0.9600 .
C11 H11C 0.9600 .
C11 H11D 0.9600 .
C11 H11E 0.9600 .
C13 H13A 0.9600 .
C13 H13B 0.9600 .
C13 H13C 0.9600 .
C15 H15A 0.9600 .
C15 H15B 0.9600 .
C15 H15C 0.9600 .
