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#$Date: 2024-08-05 20:35:13 +0300 (Mon, 05 Aug 2024) $
#$Revision: 293717 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/32/7133284.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_7133284
loop_
_publ_author_name
'Yang, Ji Seon'
'Kim, Sung-Gon'
_publ_section_title
;
 Catalytic enantioselective [3+2] and [4+2]-annulation of cyclic
 N-sulfonyl ketimines with γ- or
 δ-hydroxy-α,β-unsaturated ketones.
;
_journal_issue                   61
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              7954
_journal_page_last               7957
_journal_paper_doi               10.1039/d4cc02734e
_journal_volume                  60
_journal_year                    2024
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C21 H21 N O6 S'
_chemical_formula_sum            'C21 H21 N O6 S'
_chemical_formula_weight         415.45
_space_group_crystal_system      tetragonal
_space_group_IT_number           92
_space_group_name_Hall           'P 4abw 2nw'
_space_group_name_H-M_alt        'P 41 21 2'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2024-06-03 deposited with the CCDC.	2024-07-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   8.4145(3)
_cell_length_b                   8.4145(3)
_cell_length_c                   56.119(4)
_cell_measurement_reflns_used    7737
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      20.77
_cell_measurement_theta_min      2.45
_cell_volume                     3973.4(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_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 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      223(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1444
_diffrn_reflns_av_unetI/netI     0.0604
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       74
_diffrn_reflns_limit_l_min       -74
_diffrn_reflns_number            98435
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.275
_diffrn_reflns_theta_min         2.448
_exptl_absorpt_coefficient_mu    0.202
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6765
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.389
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             1744
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.135
_exptl_crystal_size_min          0.054
_refine_diff_density_max         0.204
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details
; 
 Flack x determined using 879 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.03(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         4926
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.1172
_refine_ls_R_factor_gt           0.0470
_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)+(0.0357P)²+1.6889P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0918
_refine_ls_wR_factor_ref         0.1172
_reflns_Friedel_coverage         0.633
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                2955
_reflns_number_total             4926
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4cc02734e2.cif
_cod_data_source_block           KGU_24_06_a
_cod_depositor_comments
'Adding full bibliography for 7133283--7133284.cif.'
_cod_original_cell_volume        3973.5(4)
_cod_database_code               7133284
_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   0.957
_shelx_estimated_absorpt_t_max   0.989
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y+1/2, x+1/2, z+1/4'
'y+1/2, -x+1/2, z+3/4'
'-x+1/2, y+1/2, -z+1/4'
'x+1/2, -y+1/2, -z+3/4'
'y, x, -z'
'-y, -x, -z+1/2'
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
S1 S 0.55077(11) 0.14970(12) 0.45343(2) 0.0420(2) Uani 1 1 d . . . . .
O1 O 0.9409(3) 0.2917(3) 0.45704(4) 0.0432(6) Uani 1 1 d . . . . .
O2 O 0.6872(3) 0.5820(3) 0.43320(5) 0.0576(8) Uani 1 1 d . . . . .
O3 O 0.9067(3) 0.6058(3) 0.45583(5) 0.0527(7) Uani 1 1 d . . . . .
O4 O 0.7478(4) 0.2008(4) 0.36498(5) 0.0708(10) Uani 1 1 d . . . . .
O006 O 0.5926(4) -0.0153(3) 0.45434(5) 0.0653(9) Uani 1 1 d . . . . .
O007 O 0.3957(3) 0.1831(4) 0.44448(5) 0.0707(10) Uani 1 1 d . . . . .
N1 N 0.6834(4) 0.2585(4) 0.43964(5) 0.0429(8) Uani 1 1 d . . . . .
C1 C 0.5840(4) 0.2415(4) 0.48095(6) 0.0388(9) Uani 1 1 d . . . . .
C2 C 0.4980(5) 0.2166(5) 0.50166(7) 0.0467(10) Uani 1 1 d . . . . .
H2 H 0.413404 0.143685 0.502240 0.056 Uiso 1 1 calc R U . . .
C3 C 0.5424(5) 0.3042(5) 0.52148(7) 0.0544(11) Uani 1 1 d . . . . .
H3 H 0.487073 0.290402 0.535884 0.065 Uiso 1 1 calc R U . . .
C4 C 0.6668(6) 0.4116(5) 0.52042(7) 0.0549(11) Uani 1 1 d . . . . .
H4 H 0.693583 0.470775 0.534047 0.066 Uiso 1 1 calc R U . . .
C5 C 0.7520(5) 0.4332(5) 0.49969(7) 0.0482(10) Uani 1 1 d . . . . .
H5 H 0.837088 0.505422 0.499120 0.058 Uiso 1 1 calc R U . . .
C6 C 0.7096(4) 0.3462(4) 0.47968(6) 0.0403(9) Uani 1 1 d . . . . .
C7 C 0.7851(4) 0.3528(4) 0.45523(6) 0.0376(8) Uani 1 1 d . . . . .
C8 C 1.0143(4) 0.2766(5) 0.43383(7) 0.0478(10) Uani 1 1 d . . . . .
H8A H 1.121856 0.233667 0.435641 0.057 Uiso 1 1 calc R U . . .
H8AB H 1.022682 0.381719 0.426427 0.057 Uiso 1 1 calc R U . . .
C9 C 0.9181(5) 0.1680(5) 0.41787(7) 0.0495(10) Uani 1 1 d . . . . .
H9A H 0.918647 0.060288 0.424512 0.059 Uiso 1 1 calc R U . . .
H9AB H 0.967449 0.163784 0.402067 0.059 Uiso 1 1 calc R U . . .
C10 C 0.7476(4) 0.2252(5) 0.41547(6) 0.0413(9) Uani 1 1 d . . . . .
H10 H 0.749083 0.326561 0.406508 0.050 Uiso 1 1 calc R U . . .
C11 C 0.7858(5) 0.5271(5) 0.44613(7) 0.0429(9) Uani 1 1 d . . . . .
C12 C 0.9197(6) 0.7745(5) 0.45003(9) 0.0684(14) Uani 1 1 d . . . . .
H12A H 0.976222 0.787557 0.434882 0.082 Uiso 1 1 calc R U . . .
H12B H 0.813418 0.820637 0.448311 0.082 Uiso 1 1 calc R U . . .
C13 C 1.0054(9) 0.8557(6) 0.46887(13) 0.126(3) Uani 1 1 d . . . . .
H13A H 1.009454 0.968607 0.465419 0.190 Uiso 1 1 calc R U . . .
H13B H 1.112615 0.813962 0.469866 0.190 Uiso 1 1 calc R U . . .
H13C H 0.951313 0.838917 0.483928 0.190 Uiso 1 1 calc R U . . .
C14 C 0.6431(5) 0.1079(5) 0.40170(7) 0.0549(11) Uani 1 1 d . . . . .
H14A H 0.640925 0.005557 0.410024 0.066 Uiso 1 1 calc R U . . .
H14B H 0.534108 0.148541 0.400859 0.066 Uiso 1 1 calc R U . . .
C15 C 0.7084(5) 0.0851(5) 0.37658(7) 0.0501(11) Uani 1 1 d . . . . .
C16 C 0.7233(5) -0.0781(5) 0.36664(7) 0.0438(10) Uani 1 1 d . . . . .
C17 C 0.7989(5) -0.0984(5) 0.34476(7) 0.0518(11) Uani 1 1 d . . . . .
H17 H 0.838659 -0.009673 0.336513 0.062 Uiso 1 1 calc R U . . .
C18 C 0.8155(5) -0.2490(6) 0.33516(7) 0.0593(12) Uani 1 1 d . . . . .
H18 H 0.867660 -0.261572 0.320466 0.071 Uiso 1 1 calc R U . . .
C19 C 0.7565(5) -0.3813(6) 0.34684(8) 0.0581(12) Uani 1 1 d . . . . .
H19 H 0.767006 -0.482939 0.340083 0.070 Uiso 1 1 calc R U . . .
C20 C 0.6824(5) -0.3618(6) 0.36842(8) 0.0630(12) Uani 1 1 d . . . . .
H20 H 0.642012 -0.450760 0.376548 0.076 Uiso 1 1 calc R U . . .
C21 C 0.6669(5) -0.2118(5) 0.37830(8) 0.0577(12) Uani 1 1 d . . . . .
H21 H 0.617077 -0.200530 0.393195 0.069 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 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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
O007 S1 O006 115.4(2) . . ?
O007 S1 N1 110.29(19) . . ?
O006 S1 N1 113.02(18) . . ?
O007 S1 C1 111.71(17) . . ?
O006 S1 C1 110.92(17) . . ?
N1 S1 C1 93.52(17) . . ?
C7 O1 C8 111.3(3) . . ?
C11 O3 C12 116.7(3) . . ?
C7 N1 C10 115.9(3) . . ?
C7 N1 S1 114.9(2) . . ?
C10 N1 S1 125.0(2) . . ?
C6 C1 C2 122.8(4) . . ?
C6 C1 S1 111.0(3) . . ?
C2 C1 S1 126.2(3) . . ?
C1 C2 C3 116.9(4) . . ?
C1 C2 H2 121.6 . . ?
C3 C2 H2 121.6 . . ?
C4 C3 C2 121.1(4) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C5 C4 C3 121.0(4) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
C4 C5 C6 118.7(4) . . ?
C4 C5 H5 120.7 . . ?
C6 C5 H5 120.7 . . ?
C1 C6 C5 119.5(3) . . ?
C1 C6 C7 113.2(3) . . ?
C5 C6 C7 127.3(4) . . ?
O1 C7 N1 112.9(3) . . ?
O1 C7 C6 108.2(3) . . ?
N1 C7 C6 106.1(3) . . ?
O1 C7 C11 111.4(3) . . ?
N1 C7 C11 108.6(3) . . ?
C6 C7 C11 109.6(3) . . ?
O1 C8 C9 110.9(3) . . ?
O1 C8 H8A 109.4 . . ?
C9 C8 H8A 109.5 . . ?
O1 C8 H8AB 109.4 . . ?
C9 C8 H8AB 109.5 . . ?
H8A C8 H8AB 108.0 . . ?
C8 C9 C10 111.5(3) . . ?
C8 C9 H9A 109.3 . . ?
C10 C9 H9A 109.3 . . ?
C8 C9 H9AB 109.3 . . ?
C10 C9 H9AB 109.3 . . ?
H9A C9 H9AB 108.0 . . ?
N1 C10 C9 108.8(3) . . ?
N1 C10 C14 111.9(3) . . ?
C9 C10 C14 112.5(3) . . ?
N1 C10 H10 107.8 . . ?
C9 C10 H10 107.8 . . ?
C14 C10 H10 107.8 . . ?
O2 C11 O3 126.0(4) . . ?
O2 C11 C7 124.2(4) . . ?
O3 C11 C7 109.7(3) . . ?
C13 C12 O3 109.4(4) . . ?
C13 C12 H12A 109.8 . . ?
O3 C12 H12A 109.8 . . ?
C13 C12 H12B 109.8 . . ?
O3 C12 H12B 109.8 . . ?
H12A C12 H12B 108.2 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 C10 109.9(3) . . ?
C15 C14 H14A 109.7 . . ?
C10 C14 H14A 109.7 . . ?
C15 C14 H14B 109.7 . . ?
C10 C14 H14B 109.7 . . ?
H14A C14 H14B 108.2 . . ?
O4 C15 C16 121.0(4) . . ?
O4 C15 C14 119.4(4) . . ?
C16 C15 C14 119.6(4) . . ?
C21 C16 C17 118.2(4) . . ?
C21 C16 C15 123.0(4) . . ?
C17 C16 C15 118.8(4) . . ?
C18 C17 C16 120.1(4) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C17 C18 C19 121.0(4) . . ?
C17 C18 H18 119.5 . . ?
C19 C18 H18 119.5 . . ?
C20 C19 C18 119.0(4) . . ?
C20 C19 H19 120.5 . . ?
C18 C19 H19 120.5 . . ?
C19 C20 C21 120.3(4) . . ?
C19 C20 H20 119.8 . . ?
C21 C20 H20 119.8 . . ?
C20 C21 C16 121.3(4) . . ?
C20 C21 H21 119.4 . . ?
C16 C21 H21 119.4 . . ?
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
S1 O007 1.426(3) . ?
S1 O006 1.433(3) . ?
S1 N1 1.638(3) . ?
S1 C1 1.750(4) . ?
O1 C7 1.412(4) . ?
O1 C8 1.447(4) . ?
O2 C11 1.195(4) . ?
O3 C11 1.331(5) . ?
O3 C12 1.461(5) . ?
O4 C15 1.217(5) . ?
N1 C7 1.459(5) . ?
N1 C10 1.487(4) . ?
C1 C6 1.377(5) . ?
C1 C2 1.385(5) . ?
C2 C3 1.385(5) . ?
C2 H2 0.9400 . ?
C3 C4 1.385(6) . ?
C3 H3 0.9400 . ?
C4 C5 1.378(5) . ?
C4 H4 0.9400 . ?
C5 C6 1.387(5) . ?
C5 H5 0.9400 . ?
C6 C7 1.513(5) . ?
C7 C11 1.553(5) . ?
C8 C9 1.513(5) . ?
C8 H8A 0.9800 . ?
C8 H8AB 0.9800 . ?
C9 C10 1.520(5) . ?
C9 H9A 0.9800 . ?
C9 H9AB 0.9800 . ?
C10 C14 1.531(5) . ?
C10 H10 0.9900 . ?
C12 C13 1.451(7) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 H13C 0.9700 . ?
C14 C15 1.525(5) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C15 C16 1.487(5) . ?
C16 C21 1.386(6) . ?
C16 C17 1.393(5) . ?
C17 C18 1.384(6) . ?
C17 H17 0.9400 . ?
C18 C19 1.384(6) . ?
C18 H18 0.9400 . ?
C19 C20 1.372(6) . ?
C19 H19 0.9400 . ?
C20 C21 1.384(6) . ?
C20 H20 0.9400 . ?
C21 H21 0.9400 . ?
