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#$Date: 2022-02-03 22:38:11 +0200 (Thu, 03 Feb 2022) $
#$Revision: 272461 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/92/4519291.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_4519291
loop_
_publ_author_name
'Liu, Yun'
'Chen, Yushuang'
'Yihuo, Aying'
'Zhou, Yuqiao'
'Liu, Xiaohua'
'Lin, Lili'
'Feng, Xiaoming'
_publ_section_title
;
 Diastereodivergent Synthesis of Chiral α-Aminoketones via a Catalytic
 O--H Insertion/Barnes--Claisen Rearrangement Reaction
;
_journal_name_full               'ACS Catalysis'
_journal_page_first              1784
_journal_page_last               1790
_journal_paper_doi               10.1021/acscatal.1c05789
_journal_year                    2022
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C20 H21 N O4 S'
_chemical_formula_sum            'C20 H21 N O4 S'
_chemical_formula_weight         371.44
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 94.297(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   22.954(3)
_cell_length_b                   8.0412(11)
_cell_length_c                   10.4938(14)
_cell_measurement_reflns_used    9785
_cell_measurement_temperature    172(2)
_cell_measurement_theta_max      68.29
_cell_measurement_theta_min      4.22
_cell_volume                     1931.5(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT (Sheldrick 2008)'
_diffrn_ambient_temperature      172(2)
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'Bruker D8 Venture Photon II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0414
_diffrn_reflns_av_unetI/netI     0.0329
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            20837
_diffrn_reflns_point_group_measured_fraction_full 0.957
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.435
_diffrn_reflns_theta_min         3.862
_exptl_absorpt_coefficient_mu    1.692
_exptl_absorpt_correction_T_max  0.8508
_exptl_absorpt_correction_T_min  0.6529
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_description       block
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.322
_exptl_crystal_size_mid          0.189
_exptl_crystal_size_min          0.154
_refine_diff_density_max         0.209
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details
; 
 Flack x determined using 1471 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.085(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     241
_refine_ls_number_reflns         3388
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0303
_refine_ls_R_factor_gt           0.0298
_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/[σ²(Fo²)+(0.0437P)²+0.7411P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0800
_refine_ls_wR_factor_ref         0.0805
_reflns_Friedel_coverage         0.815
_reflns_Friedel_fraction_full    0.932
_reflns_Friedel_fraction_max     0.929
_reflns_number_gt                3337
_reflns_number_total             3388
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cs1c05789_si_002.cif
_cod_data_source_block           liy012
_cod_original_cell_volume        1931.5(5)
_cod_original_sg_symbol_H-M      'C 2'
_cod_database_code               4519291
_shelx_shelxl_version_number     2018/3
_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. 
;
_shelx_estimated_absorpt_t_min   0.612
_shelx_estimated_absorpt_t_max   0.781
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -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
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S S 0.51247(2) 0.42157(7) 0.72088(5) 0.03144(16) Uani 1 1 d . . . . .
O1 O 0.50474(9) 0.2900(2) 0.80903(19) 0.0427(4) Uani 1 1 d . . . . .
O2 O 0.46403(8) 0.4756(3) 0.63558(18) 0.0425(5) Uani 1 1 d . . . . .
O3 O 0.66098(11) 0.5757(3) 0.6772(2) 0.0542(5) Uani 1 1 d . . . . .
O4 O 0.68497(10) 0.3199(3) 0.9286(2) 0.0568(6) Uani 1 1 d . . . . .
N N 0.56250(9) 0.3653(3) 0.62922(19) 0.0336(5) Uani 1 1 d D . . . .
H1N H 0.5608(14) 0.411(5) 0.553(2) 0.050(8) Uiso 1 1 d D . . . .
C1 C 0.53750(10) 0.5949(3) 0.8111(2) 0.0290(5) Uani 1 1 d . . . . .
C2 C 0.52999(11) 0.7530(3) 0.7586(2) 0.0363(5) Uani 1 1 d . . . . .
H2 H 0.513365 0.766038 0.673568 0.044 Uiso 1 1 calc R U . . .
C3 C 0.54672(12) 0.8901(3) 0.8303(2) 0.0382(6) Uani 1 1 d . . . . .
H3 H 0.541146 0.997993 0.794537 0.046 Uiso 1 1 calc R U . . .
C4 C 0.57188(10) 0.8732(3) 0.9554(3) 0.0352(5) Uani 1 1 d . . . . .
C5 C 0.58048(11) 0.7145(4) 1.0038(2) 0.0364(6) Uani 1 1 d . . . . .
H5 H 0.598786 0.701030 1.087440 0.044 Uiso 1 1 calc R U . . .
C6 C 0.56316(11) 0.5742(3) 0.9339(2) 0.0332(5) Uani 1 1 d . . . . .
H6 H 0.568768 0.466218 0.969443 0.040 Uiso 1 1 calc R U . . .
C7 C 0.58695(13) 1.0254(4) 1.0340(3) 0.0492(7) Uani 1 1 d . . . . .
H7A H 0.598574 0.992439 1.122187 0.074 Uiso 1 1 calc R U . . .
H7B H 0.552800 1.098695 1.033082 0.074 Uiso 1 1 calc R U . . .
H7C H 0.619293 1.084435 0.998126 0.074 Uiso 1 1 calc R U . . .
C11 C 0.61870(10) 0.3020(3) 0.6819(2) 0.0307(5) Uani 1 1 d . . . . .
H11 H 0.612508 0.225917 0.755052 0.037 Uiso 1 1 calc R U . . .
C12 C 0.64824(11) 0.2039(3) 0.5760(2) 0.0332(5) Uani 1 1 d . . . . .
H12 H 0.653411 0.282547 0.503848 0.040 Uiso 1 1 calc R U . . .
C13 C 0.61071(13) 0.0640(4) 0.5249(3) 0.0489(7) Uani 1 1 d . . . . .
H13 H 0.601604 -0.022926 0.581409 0.059 Uiso 1 1 calc R U . . .
C14 C 0.5897(2) 0.0556(6) 0.4049(4) 0.0848(15) Uani 1 1 d D . . . .
H14A H 0.551962 -0.001970 0.400688 0.102 Uiso 1 1 d DR U . . .
H14B H 0.616893 -0.006040 0.354859 0.102 Uiso 1 1 d DR U . . .
C15 C 0.66054(11) 0.4417(4) 0.7273(2) 0.0370(6) Uani 1 1 d . . . . .
C16 C 0.70211(12) 0.4057(4) 0.8477(3) 0.0474(7) Uani 1 1 d . . . . .
C17 C 0.76093(19) 0.4835(8) 0.8544(5) 0.0985(17) Uani 1 1 d . . . . .
H17A H 0.788399 0.414839 0.907527 0.148 Uiso 1 1 calc R U . . .
H17B H 0.758912 0.594755 0.892056 0.148 Uiso 1 1 calc R U . . .
H17C H 0.774306 0.492397 0.768177 0.148 Uiso 1 1 calc R U . . .
C21 C 0.70873(10) 0.1433(3) 0.6254(2) 0.0322(5) Uani 1 1 d . . . . .
C22 C 0.75817(13) 0.2020(4) 0.5722(3) 0.0470(7) Uani 1 1 d . . . . .
H22 H 0.754270 0.282162 0.505589 0.056 Uiso 1 1 calc R U . . .
C23 C 0.81325(14) 0.1453(5) 0.6147(4) 0.0626(10) Uani 1 1 d . . . . .
H23 H 0.846674 0.185500 0.576176 0.075 Uiso 1 1 calc R U . . .
C24 C 0.81966(14) 0.0325(5) 0.7113(4) 0.0644(11) Uani 1 1 d . . . . .
H24 H 0.857544 -0.004715 0.741066 0.077 Uiso 1 1 calc R U . . .
C25 C 0.77108(16) -0.0281(5) 0.7661(3) 0.0604(9) Uani 1 1 d . . . . .
H25 H 0.775509 -0.107200 0.833380 0.073 Uiso 1 1 calc R U . . .
C26 C 0.71574(13) 0.0269(4) 0.7228(3) 0.0435(6) Uani 1 1 d . . . . .
H26 H 0.682383 -0.015717 0.760155 0.052 Uiso 1 1 calc R U . . .
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'
N N 0.0311 0.0180 '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'
S S 0.3331 0.5567 '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
_geom_angle_publ_flag
O1 S O2 119.94(12) . . ?
O1 S N 107.88(12) . . ?
O2 S N 105.32(11) . . ?
O1 S C1 106.89(11) . . ?
O2 S C1 107.53(11) . . ?
N S C1 108.94(11) . . ?
C11 N S 121.35(16) . . ?
C6 C1 C2 120.6(2) . . ?
C6 C1 S 120.30(19) . . ?
C2 C1 S 119.05(18) . . ?
C3 C2 C1 119.7(2) . . ?
C2 C3 C4 120.9(2) . . ?
C5 C4 C3 118.1(2) . . ?
C5 C4 C7 122.0(2) . . ?
C3 C4 C7 119.8(2) . . ?
C4 C5 C6 121.9(2) . . ?
C1 C6 C5 118.6(2) . . ?
N C11 C15 112.3(2) . . ?
N C11 C12 109.04(18) . . ?
C15 C11 C12 107.25(19) . . ?
C13 C12 C21 111.6(2) . . ?
C13 C12 C11 111.6(2) . . ?
C21 C12 C11 110.65(19) . . ?
C14 C13 C12 122.9(4) . . ?
O3 C15 C11 123.3(2) . . ?
O3 C15 C16 119.9(2) . . ?
C11 C15 C16 116.7(2) . . ?
O4 C16 C17 124.1(3) . . ?
O4 C16 C15 118.4(2) . . ?
C17 C16 C15 117.5(3) . . ?
C22 C21 C26 118.3(3) . . ?
C22 C21 C12 120.4(2) . . ?
C26 C21 C12 121.3(2) . . ?
C21 C22 C23 120.9(3) . . ?
C24 C23 C22 120.3(3) . . ?
C23 C24 C25 120.0(3) . . ?
C24 C25 C26 119.9(3) . . ?
C21 C26 C25 120.6(3) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S O1 1.425(2) . ?
S O2 1.4414(19) . ?
S N 1.617(2) . ?
S C1 1.758(3) . ?
O3 C15 1.199(4) . ?
O4 C16 1.184(4) . ?
N C11 1.457(3) . ?
C1 C6 1.386(3) . ?
C1 C2 1.391(4) . ?
C2 C3 1.373(4) . ?
C3 C4 1.401(4) . ?
C4 C5 1.383(4) . ?
C4 C7 1.502(4) . ?
C5 C6 1.387(4) . ?
C11 C15 1.530(3) . ?
C11 C12 1.559(3) . ?
C12 C13 1.493(4) . ?
C12 C21 1.525(3) . ?
C13 C14 1.316(5) . ?
C15 C16 1.553(4) . ?
C16 C17 1.485(5) . ?
C21 C22 1.385(4) . ?
C21 C26 1.386(4) . ?
C22 C23 1.386(5) . ?
C23 C24 1.361(6) . ?
C24 C25 1.381(6) . ?
C25 C26 1.389(4) . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 S N C11 -50.6(2) . . . . ?
O2 S N C11 -179.84(19) . . . . ?
C1 S N C11 65.1(2) . . . . ?
O1 S C1 C6 20.4(2) . . . . ?
O2 S C1 C6 150.41(19) . . . . ?
N S C1 C6 -95.9(2) . . . . ?
O1 S C1 C2 -158.19(19) . . . . ?
O2 S C1 C2 -28.2(2) . . . . ?
N S C1 C2 85.5(2) . . . . ?
C6 C1 C2 C3 -1.8(4) . . . . ?
S C1 C2 C3 176.82(19) . . . . ?
C1 C2 C3 C4 0.7(4) . . . . ?
C2 C3 C4 C5 1.3(4) . . . . ?
C2 C3 C4 C7 -176.9(2) . . . . ?
C3 C4 C5 C6 -2.2(4) . . . . ?
C7 C4 C5 C6 175.9(2) . . . . ?
C2 C1 C6 C5 0.8(4) . . . . ?
S C1 C6 C5 -177.74(19) . . . . ?
C4 C5 C6 C1 1.2(4) . . . . ?
S N C11 C15 -80.5(2) . . . . ?
S N C11 C12 160.79(18) . . . . ?
N C11 C12 C13 -58.2(3) . . . . ?
C15 C11 C12 C13 -180.0(2) . . . . ?
N C11 C12 C21 177.0(2) . . . . ?
C15 C11 C12 C21 55.2(3) . . . . ?
C21 C12 C13 C14 -118.2(3) . . . . ?
C11 C12 C13 C14 117.5(3) . . . . ?
N C11 C15 O3 -32.5(3) . . . . ?
C12 C11 C15 O3 87.2(3) . . . . ?
N C11 C15 C16 144.9(2) . . . . ?
C12 C11 C15 C16 -95.3(2) . . . . ?
O3 C15 C16 O4 143.7(3) . . . . ?
C11 C15 C16 O4 -33.8(4) . . . . ?
O3 C15 C16 C17 -35.6(4) . . . . ?
C11 C15 C16 C17 146.9(3) . . . . ?
C13 C12 C21 C22 119.4(3) . . . . ?
C11 C12 C21 C22 -115.7(3) . . . . ?
C13 C12 C21 C26 -59.5(3) . . . . ?
C11 C12 C21 C26 65.3(3) . . . . ?
C26 C21 C22 C23 0.3(4) . . . . ?
C12 C21 C22 C23 -178.7(3) . . . . ?
C21 C22 C23 C24 -1.0(5) . . . . ?
C22 C23 C24 C25 1.0(5) . . . . ?
C23 C24 C25 C26 -0.2(5) . . . . ?
C22 C21 C26 C25 0.5(4) . . . . ?
C12 C21 C26 C25 179.5(3) . . . . ?
C24 C25 C26 C21 -0.5(5) . . . . ?
