#------------------------------------------------------------------------------
#$Date: 2025-08-20 20:34:49 +0200 (Wed 20 de Aug de 2025) $
#$Revision: 301835 $
#$URL: svn://www.crystallography.net/cod/cif/4/13/41/4134196.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_4134196
loop_
_publ_author_name
'Kondoh, Azusa'
'Ishikawa, Sho'
'Terada, Masahiro'
_publ_section_title
;
 Development of Chiral Ureates as Chiral Strong Brønsted Base Catalysts.
;
_journal_issue                   8
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              3724
_journal_page_last               3728
_journal_paper_doi               10.1021/jacs.9b13922
_journal_volume                  142
_journal_year                    2020
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'
_chemical_formula_moiety         'C23 H23 N O5 S2'
_chemical_formula_sum            'C23 H23 N O5 S2'
_chemical_formula_weight         457.56
_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     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.0000
_cell_angle_beta                 101.819(7)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            2
_cell_length_a                   8.4797(14)
_cell_length_b                   9.7632(17)
_cell_length_c                   13.361(2)
_cell_measurement_reflns_used    11391
_cell_measurement_temperature    150
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      3.10
_cell_volume                     1082.7(3)
_computing_cell_refinement       'CrystalClear-SM Auto 2.0 r15'
_computing_data_collection       'CrystalClear-SM Auto 2.0 r15 (Rigaku, 2011)'
_computing_data_reduction        'CrystalClear-SM Auto 2.0 r15'
_computing_molecular_graphics    'CrystalStructure 4.3'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2019)'
_computing_structure_refinement  'SHELXL Version 2013/4 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150
_diffrn_detector_area_resol_mean 13.653
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Rigaku XtaLAB mini'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0627
_diffrn_reflns_av_unetI/netI     0.0759
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_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            11463
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.485
_diffrn_reflns_theta_min         3.115
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.281
_exptl_absorpt_correction_T_max  0.945
_exptl_absorpt_correction_T_min  0.692
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             480.00
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.37
_refine_diff_density_min         -0.36
_refine_ls_abs_structure_details
;
 Flack x determined using 2189 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     280
_refine_ls_number_reflns         4948
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0431
_refine_ls_R_factor_gt           0.0421
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0498P)²+0.2242P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1074
_refine_ls_wR_factor_ref         0.1084
_reflns_Friedel_coverage         0.884
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.992
_reflns_number_gt                4819
_reflns_number_total             4948
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            ja9b13922_si_002.cif
_cod_data_source_block           01
_cod_depositor_comments
'Adding full bibliography for 4134194--4134196.cif.'
_cod_database_code               4134196
_shelxl_version_number           2013-4
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,1/2+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
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.60633(8) 0.83409(7) 0.07072(5) 0.01721(17) Uani 1 1 d . . . . .
S2 S 0.51635(9) 0.99624(7) 0.44735(6) 0.02127(18) Uani 1 1 d . . . . .
O3 O 0.6368(3) 0.7140(2) 0.01479(17) 0.0234(5) Uani 1 1 d . . . . .
O5 O 0.3767(3) 0.6487(3) 0.17770(19) 0.0289(5) Uani 1 1 d . . . . .
O8 O 0.4597(3) 0.9096(2) 0.03646(17) 0.0249(5) Uani 1 1 d . . . . .
O13 O 0.5989(3) 1.1187(3) 0.4253(2) 0.0312(6) Uani 1 1 d . . . . .
O14 O 0.5434(3) 0.9500(3) 0.55192(17) 0.0329(6) Uani 1 1 d . . . . .
N7 N 0.6118(3) 0.5317(3) 0.22442(19) 0.0211(5) Uani 1 1 d . . . . .
C4 C 0.5233(4) 0.6468(3) 0.2000(2) 0.0198(6) Uani 1 1 d . . . . .
C6 C 0.3066(3) 1.0191(3) 0.4031(2) 0.0197(6) Uani 1 1 d . . . . .
C9 C 0.7732(4) 0.9456(3) 0.0793(2) 0.0181(6) Uani 1 1 d . . . . .
C10 C 0.5721(4) 0.8597(3) 0.3733(2) 0.0218(6) Uani 1 1 d . . . . .
H10A H 0.6873 0.8377 0.3988 0.026 Uiso 1 1 calc R U . . .
H10B H 0.5084 0.7773 0.3823 0.026 Uiso 1 1 calc R U . . .
C11 C 0.6170(3) 0.7815(3) 0.2021(2) 0.0171(6) Uani 1 1 d . . . . .
H11 H 0.7321 0.7659 0.2360 0.020 Uiso 1 1 calc R U . . .
C12 C 0.5452(4) 0.8942(3) 0.2599(2) 0.0209(6) Uani 1 1 d . . . . .
H12A H 0.5966 0.9831 0.2509 0.025 Uiso 1 1 calc R U . . .
H12B H 0.4283 0.9027 0.2314 0.025 Uiso 1 1 calc R U . . .
C15 C 1.1185(4) 0.5394(4) 0.2949(3) 0.0260(7) Uani 1 1 d . . . . .
H15 H 1.2328 0.5449 0.3105 0.031 Uiso 1 1 calc R U . . .
C16 C 0.5307(4) 0.3977(3) 0.2209(3) 0.0270(7) Uani 1 1 d . . . . .
H16A H 0.6115 0.3256 0.2406 0.032 Uiso 1 1 calc R U . . .
H16B H 0.4701 0.3805 0.1513 0.032 Uiso 1 1 calc R U . . .
H16C H 0.4567 0.3980 0.2684 0.032 Uiso 1 1 calc R U . . .
C17 C 0.7467(4) 1.0844(3) 0.0669(2) 0.0233(6) Uani 1 1 d . . . . .
H17 H 0.6409 1.1212 0.0565 0.028 Uiso 1 1 calc R U . . .
C18 C 0.0815(4) 1.1657(4) 0.3461(3) 0.0317(8) Uani 1 1 d . . . . .
H18 H 0.0384 1.2535 0.3256 0.038 Uiso 1 1 calc R U . . .
C19 C 1.0581(4) 0.9756(4) 0.0976(3) 0.0280(7) Uani 1 1 d . . . . .
H19 H 1.1642 0.9394 0.1080 0.034 Uiso 1 1 calc R U . . .
C20 C 0.9270(4) 0.8882(3) 0.0951(2) 0.0212(6) Uani 1 1 d . . . . .
H20 H 0.9421 0.7922 0.1040 0.025 Uiso 1 1 calc R U . . .
C21 C 0.8658(4) 0.5437(3) 0.3499(2) 0.0243(6) Uani 1 1 d . . . . .
H21 H 0.8072 0.5496 0.4032 0.029 Uiso 1 1 calc R U . . .
C22 C 0.8695(4) 0.5178(3) 0.1706(2) 0.0210(6) Uani 1 1 d . . . . .
H22 H 0.8136 0.5058 0.1019 0.025 Uiso 1 1 calc R U . . .
C23 C 0.2483(4) 1.1476(3) 0.3722(3) 0.0262(7) Uani 1 1 d . . . . .
H23 H 0.3196 1.2216 0.3689 0.031 Uiso 1 1 calc R U . . .
C24 C 0.7850(3) 0.5310(3) 0.2492(2) 0.0183(6) Uani 1 1 d . . . . .
C25 C 1.0366(4) 0.5226(3) 0.1941(2) 0.0239(6) Uani 1 1 d . . . . .
H25 H 1.0955 0.5144 0.1410 0.029 Uiso 1 1 calc R U . . .
C26 C -0.0208(4) 1.0571(4) 0.3499(3) 0.0311(7) Uani 1 1 d . . . . .
H26 H -0.1340 1.0706 0.3323 0.037 Uiso 1 1 calc R U . . .
C27 C 0.2052(4) 0.9089(3) 0.4074(3) 0.0274(7) Uani 1 1 d . . . . .
H27 H 0.2481 0.8215 0.4294 0.033 Uiso 1 1 calc R U . . .
C28 C 1.0324(4) 0.5479(4) 0.3723(2) 0.0269(7) Uani 1 1 d . . . . .
H28 H 1.0881 0.5567 0.4413 0.032 Uiso 1 1 calc R U . . .
C29 C 1.0327(5) 1.1152(4) 0.0848(3) 0.0323(8) Uani 1 1 d . . . . .
H29 H 1.1220 1.1745 0.0862 0.039 Uiso 1 1 calc R U . . .
C30 C 0.8798(5) 1.1691(4) 0.0700(3) 0.0318(8) Uani 1 1 d . . . . .
H30 H 0.8648 1.2651 0.0619 0.038 Uiso 1 1 calc R U . . .
C31 C 0.0401(4) 0.9286(4) 0.3791(3) 0.0328(8) Uani 1 1 d . . . . .
H31 H -0.0312 0.8537 0.3797 0.039 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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.1246 0.1234
;
International Tables for Crystallography
(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
O8 S1 O3 119.17(14) . . ?
O8 S1 C9 109.45(15) . . ?
O3 S1 C9 107.94(13) . . ?
O8 S1 C11 108.78(13) . . ?
O3 S1 C11 107.03(14) . . ?
C9 S1 C11 103.32(13) . . ?
O14 S2 O13 117.98(16) . . ?
O14 S2 C6 108.21(14) . . ?
O13 S2 C6 108.85(15) . . ?
O14 S2 C10 107.25(16) . . ?
O13 S2 C10 108.13(15) . . ?
C6 S2 C10 105.77(14) . . ?
C4 N7 C24 123.3(2) . . ?
C4 N7 C16 119.8(2) . . ?
C24 N7 C16 116.8(3) . . ?
O5 C4 N7 124.0(3) . . ?
O5 C4 C11 119.4(3) . . ?
N7 C4 C11 116.6(2) . . ?
C23 C6 C27 122.1(3) . . ?
C23 C6 S2 119.3(2) . . ?
C27 C6 S2 118.5(2) . . ?
C17 C9 C20 122.5(3) . . ?
C17 C9 S1 119.2(3) . . ?
C20 C9 S1 118.2(2) . . ?
C12 C10 S2 112.6(2) . . ?
C12 C10 H10A 109.1 . . ?
S2 C10 H10A 109.1 . . ?
C12 C10 H10B 109.1 . . ?
S2 C10 H10B 109.1 . . ?
H10A C10 H10B 107.8 . . ?
C4 C11 C12 111.4(2) . . ?
C4 C11 S1 107.6(2) . . ?
C12 C11 S1 109.7(2) . . ?
C4 C11 H11 109.4 . . ?
C12 C11 H11 109.4 . . ?
S1 C11 H11 109.4 . . ?
C10 C12 C11 110.3(2) . . ?
C10 C12 H12A 109.6 . . ?
C11 C12 H12A 109.6 . . ?
C10 C12 H12B 109.6 . . ?
C11 C12 H12B 109.6 . . ?
H12A C12 H12B 108.1 . . ?
C28 C15 C25 119.6(3) . . ?
C28 C15 H15 120.2 . . ?
C25 C15 H15 120.2 . . ?
N7 C16 H16A 109.5 . . ?
N7 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N7 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C9 C17 C30 118.0(3) . . ?
C9 C17 H17 121.0 . . ?
C30 C17 H17 121.0 . . ?
C26 C18 C23 120.4(3) . . ?
C26 C18 H18 119.8 . . ?
C23 C18 H18 119.8 . . ?
C29 C19 C20 119.7(3) . . ?
C29 C19 H19 120.1 . . ?
C20 C19 H19 120.1 . . ?
C9 C20 C19 118.2(3) . . ?
C9 C20 H20 120.9 . . ?
C19 C20 H20 120.9 . . ?
C28 C21 C24 119.5(3) . . ?
C28 C21 H21 120.2 . . ?
C24 C21 H21 120.2 . . ?
C25 C22 C24 119.1(3) . . ?
C25 C22 H22 120.5 . . ?
C24 C22 H22 120.5 . . ?
C6 C23 C18 118.2(3) . . ?
C6 C23 H23 120.9 . . ?
C18 C23 H23 120.9 . . ?
C21 C24 C22 120.8(3) . . ?
C21 C24 N7 120.2(2) . . ?
C22 C24 N7 119.0(3) . . ?
C22 C25 C15 120.4(3) . . ?
C22 C25 H25 119.8 . . ?
C15 C25 H25 119.8 . . ?
C18 C26 C31 120.5(3) . . ?
C18 C26 H26 119.7 . . ?
C31 C26 H26 119.7 . . ?
C6 C27 C31 118.8(3) . . ?
C6 C27 H27 120.6 . . ?
C31 C27 H27 120.6 . . ?
C21 C28 C15 120.5(3) . . ?
C21 C28 H28 119.7 . . ?
C15 C28 H28 119.7 . . ?
C30 C29 C19 120.8(3) . . ?
C30 C29 H29 119.6 . . ?
C19 C29 H29 119.6 . . ?
C29 C30 C17 120.8(3) . . ?
C29 C30 H30 119.6 . . ?
C17 C30 H30 119.6 . . ?
C26 C31 C27 120.0(3) . . ?
C26 C31 H31 120.0 . . ?
C27 C31 H31 120.0 . . ?
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 O8 1.437(2) . ?
S1 O3 1.442(2) . ?
S1 C9 1.770(3) . ?
S1 C11 1.813(3) . ?
S2 O14 1.441(2) . ?
S2 O13 1.446(3) . ?
S2 C6 1.770(3) . ?
S2 C10 1.781(3) . ?
O5 C4 1.218(4) . ?
N7 C4 1.354(4) . ?
N7 C24 1.438(4) . ?
N7 C16 1.474(4) . ?
C4 C11 1.534(4) . ?
C6 C23 1.380(5) . ?
C6 C27 1.385(4) . ?
C9 C17 1.378(4) . ?
C9 C20 1.395(4) . ?
C10 C12 1.523(4) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.539(4) . ?
C11 H11 1.0000 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C15 C28 1.385(5) . ?
C15 C25 1.393(5) . ?
C15 H15 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C30 1.393(5) . ?
C17 H17 0.9500 . ?
C18 C26 1.377(5) . ?
C18 C23 1.397(5) . ?
C18 H18 0.9500 . ?
C19 C29 1.385(6) . ?
C19 C20 1.396(5) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
C21 C28 1.383(4) . ?
C21 C24 1.384(4) . ?
C21 H21 0.9500 . ?
C22 C25 1.388(4) . ?
C22 C24 1.394(4) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
C25 H25 0.9500 . ?
C26 C31 1.382(6) . ?
C26 H26 0.9500 . ?
C27 C31 1.387(5) . ?
C27 H27 0.9500 . ?
C28 H28 0.9500 . ?
C29 C30 1.375(6) . ?
C29 H29 0.9500 . ?
C30 H30 0.9500 . ?
C31 H31 0.9500 . ?
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
C24 N7 C4 O5 179.1(3) . . . . ?
C16 N7 C4 O5 2.5(4) . . . . ?
C24 N7 C4 C11 -1.4(4) . . . . ?
C16 N7 C4 C11 -178.1(3) . . . . ?
O14 S2 C6 C23 118.7(3) . . . . ?
O13 S2 C6 C23 -10.7(3) . . . . ?
C10 S2 C6 C23 -126.6(3) . . . . ?
O14 S2 C6 C27 -56.9(3) . . . . ?
O13 S2 C6 C27 173.8(2) . . . . ?
C10 S2 C6 C27 57.8(3) . . . . ?
O8 S1 C9 C17 8.1(3) . . . . ?
O3 S1 C9 C17 139.2(3) . . . . ?
C11 S1 C9 C17 -107.6(3) . . . . ?
O8 S1 C9 C20 -169.7(2) . . . . ?
O3 S1 C9 C20 -38.6(3) . . . . ?
C11 S1 C9 C20 74.5(2) . . . . ?
O14 S2 C10 C12 178.5(2) . . . . ?
O13 S2 C10 C12 -53.2(3) . . . . ?
C6 S2 C10 C12 63.2(3) . . . . ?
O5 C4 C11 C12 46.7(4) . . . . ?
N7 C4 C11 C12 -132.8(3) . . . . ?
O5 C4 C11 S1 -73.6(3) . . . . ?
N7 C4 C11 S1 107.0(3) . . . . ?
O8 S1 C11 C4 85.3(2) . . . . ?
O3 S1 C11 C4 -44.7(2) . . . . ?
C9 S1 C11 C4 -158.5(2) . . . . ?
O8 S1 C11 C12 -36.1(2) . . . . ?
O3 S1 C11 C12 -166.03(19) . . . . ?
C9 S1 C11 C12 80.2(2) . . . . ?
S2 C10 C12 C11 172.1(2) . . . . ?
C4 C11 C12 C10 68.0(3) . . . . ?
S1 C11 C12 C10 -173.0(2) . . . . ?
C20 C9 C17 C30 0.3(5) . . . . ?
S1 C9 C17 C30 -177.5(2) . . . . ?
C17 C9 C20 C19 -0.5(5) . . . . ?
S1 C9 C20 C19 177.3(2) . . . . ?
C29 C19 C20 C9 0.2(5) . . . . ?
C27 C6 C23 C18 0.9(5) . . . . ?
S2 C6 C23 C18 -174.5(3) . . . . ?
C26 C18 C23 C6 -0.9(5) . . . . ?
C28 C21 C24 C22 2.1(5) . . . . ?
C28 C21 C24 N7 -177.6(3) . . . . ?
C25 C22 C24 C21 -2.3(5) . . . . ?
C25 C22 C24 N7 177.5(3) . . . . ?
C4 N7 C24 C21 91.8(4) . . . . ?
C16 N7 C24 C21 -91.4(4) . . . . ?
C4 N7 C24 C22 -87.9(4) . . . . ?
C16 N7 C24 C22 88.8(3) . . . . ?
C24 C22 C25 C15 0.4(5) . . . . ?
C28 C15 C25 C22 1.6(5) . . . . ?
C23 C18 C26 C31 -0.3(5) . . . . ?
C23 C6 C27 C31 0.5(5) . . . . ?
S2 C6 C27 C31 175.9(3) . . . . ?
C24 C21 C28 C15 0.0(5) . . . . ?
C25 C15 C28 C21 -1.8(5) . . . . ?
C20 C19 C29 C30 0.3(5) . . . . ?
C19 C29 C30 C17 -0.4(5) . . . . ?
C9 C17 C30 C29 0.2(5) . . . . ?
C18 C26 C31 C27 1.7(6) . . . . ?
C6 C27 C31 C26 -1.7(5) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168336171
