#------------------------------------------------------------------------------
#$Date: 2025-08-20 18:06:18 +0200 (Wed 20 de Aug de 2025) $
#$Revision: 301834 $
#$URL: svn://www.crystallography.net/cod/cif/4/12/13/4121369.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_4121369
loop_
_publ_author_name
'Kohsuke Ohmatsu'
'Yuichiro Ando'
'Takashi Ooi'
_publ_section_title
;
 Asymmetric Substitution at the Tetrasubstituted Chiral Carbon: Catalytic
 Ring-Opening Alkylation of Racemic 2,2-Disubstituted Aziridines with
 3-Substituted Oxindoles
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              18706
_journal_page_last               18709
_journal_paper_doi               10.1021/ja411647x
_journal_volume                  135
_journal_year                    2013
_chemical_absolute_configuration R,S
_chemical_formula_sum            'C32 H38 N2 O5 S'
_chemical_formula_weight         562.70
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.4319(16)
_cell_length_b                   16.382(4)
_cell_length_c                   27.793(7)
_cell_measurement_temperature    293(2)
_cell_volume                     2928.5(13)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type
;
Saturn724+ (4x4 bin mode)
;
_diffrn_measurement_method       dtprofit.ref
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.1223
_diffrn_reflns_av_sigmaI/netI    0.1301
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            23968
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.18
_exptl_absorpt_coefficient_mu    0.154
_exptl_absorpt_correction_T_max  0.9969
_exptl_absorpt_correction_T_min  0.9553
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_description       Prism
_exptl_crystal_F_000             1200
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.721
_refine_diff_density_min         -0.402
_refine_diff_density_rms         0.081
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.29(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     369
_refine_ls_number_reflns         6696
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.1421
_refine_ls_R_factor_gt           0.0933
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1187P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2105
_refine_ls_wR_factor_ref         0.2481
_reflns_number_gt                4186
_reflns_number_total             6696
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja411647x_si_004.cif
_cod_data_source_block           shelxs
_cod_original_cell_volume        2928.4(13)
_cod_database_code               4121369
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, 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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
S1 S 0.4477(2) 0.49035(7) 0.04359(5) 0.0326(3) Uani 1 1 d .
O3 O 0.2524(6) 0.4934(2) 0.21282(12) 0.0333(8) Uani 1 1 d .
O2 O 0.4913(6) 0.5287(2) 0.28683(12) 0.0362(9) Uani 1 1 d .
O4 O 0.6297(6) 0.4822(2) 0.07252(14) 0.0409(9) Uani 1 1 d .
O5 O 0.4728(6) 0.5075(2) -0.00641(12) 0.0421(9) Uani 1 1 d .
C24 C 0.2921(7) 0.4017(3) 0.05164(18) 0.0289(11) Uani 1 1 d .
N1 N 0.2326(7) 0.6099(3) 0.26066(14) 0.0295(10) Uani 1 1 d .
O1 O 0.3480(7) 0.6209(2) 0.33838(14) 0.0502(11) Uani 1 1 d .
C28 C 0.2206(9) 0.2740(3) 0.0897(2) 0.0352(13) Uani 1 1 d .
H28 H 0.2551 0.2335 0.1118 0.042 Uiso 1 1 calc R
C6 C -0.0588(9) 0.8043(3) 0.28604(17) 0.0314(11) Uani 1 1 d .
H6 H -0.0750 0.8457 0.3086 0.038 Uiso 1 1 calc R
C3 C -0.0105(7) 0.6828(3) 0.21685(18) 0.0287(11) Uani 1 1 d .
C29 C 0.3493(8) 0.3421(3) 0.08664(18) 0.0300(11) Uani 1 1 d .
C27 C 0.0428(9) 0.2628(3) 0.06155(17) 0.0323(11) Uani 1 1 d .
C15 C 0.1605(8) 0.6322(3) 0.13768(17) 0.0249(10) Uani 1 1 d .
C5 C -0.1763(8) 0.8054(3) 0.24410(19) 0.0345(13) Uani 1 1 d .
H5 H -0.2723 0.8470 0.2391 0.041 Uiso 1 1 calc R
C8 C 0.1025(8) 0.6815(3) 0.25921(18) 0.0298(12) Uani 1 1 d .
N2 N 0.3119(8) 0.5653(3) 0.06486(16) 0.0399(12) Uani 1 1 d .
H2 H 0.2999 0.6108 0.0497 0.048 Uiso 1 1 calc R
C9 C 0.3603(8) 0.5873(3) 0.29971(19) 0.0339(12) Uani 1 1 d .
C32 C 0.5278(8) 0.3461(3) 0.1213(2) 0.0380(13) Uani 1 1 d .
H32A H 0.5241 0.2994 0.1421 0.057 Uiso 1 1 calc R
H32B H 0.5172 0.3950 0.1402 0.057 Uiso 1 1 calc R
H32C H 0.6564 0.3465 0.1037 0.057 Uiso 1 1 calc R
C7 C 0.0838(8) 0.7415(3) 0.29454(18) 0.0335(12) Uani 1 1 d .
H7 H 0.1627 0.7398 0.3226 0.040 Uiso 1 1 calc R
C25 C 0.1124(8) 0.3932(3) 0.02333(19) 0.0338(12) Uani 1 1 d .
C2 C 0.0379(8) 0.6089(3) 0.18650(16) 0.0262(10) Uani 1 1 d .
C1 C 0.1886(8) 0.5616(3) 0.21975(18) 0.0302(11) Uani 1 1 d .
C18 C -0.1243(9) 0.6542(4) 0.07623(18) 0.0398(14) Uani 1 1 d .
H18 H -0.1475 0.5982 0.0764 0.048 Uiso 1 1 calc R
C26 C -0.0078(9) 0.3226(3) 0.02996(19) 0.0370(13) Uani 1 1 d .
H26 H -0.1281 0.3165 0.0118 0.044 Uiso 1 1 calc R
C17 C 0.0268(8) 0.6863(3) 0.10567(17) 0.0273(11) Uani 1 1 d .
C13 C 0.7430(10) 0.4272(4) 0.2946(2) 0.0454(15) Uani 1 1 d .
H13A H 0.6487 0.3903 0.2790 0.068 Uiso 1 1 calc R
H13B H 0.8349 0.3969 0.3152 0.068 Uiso 1 1 calc R
H13C H 0.8229 0.4557 0.2707 0.068 Uiso 1 1 calc R
C16 C 0.3624(8) 0.6734(3) 0.15140(19) 0.0341(12) Uani 1 1 d .
H16A H 0.4293 0.6939 0.1230 0.051 Uiso 1 1 calc R
H16B H 0.4519 0.6345 0.1669 0.051 Uiso 1 1 calc R
H16C H 0.3343 0.7177 0.1730 0.051 Uiso 1 1 calc R
C22 C 0.0558(10) 0.7714(3) 0.10321(18) 0.0371(13) Uani 1 1 d .
H22 H 0.1590 0.7954 0.1219 0.045 Uiso 1 1 calc R
C30 C 0.0360(10) 0.4542(4) -0.01240(19) 0.0428(14) Uani 1 1 d .
H30A H -0.0104 0.5023 0.0041 0.064 Uiso 1 1 calc R
H30B H -0.0775 0.4312 -0.0303 0.064 Uiso 1 1 calc R
H30C H 0.1467 0.4682 -0.0340 0.064 Uiso 1 1 calc R
C4 C -0.1516(8) 0.7444(3) 0.20931(19) 0.0300(11) Uani 1 1 d .
H4 H -0.2303 0.7456 0.1812 0.036 Uiso 1 1 calc R
C10 C 0.6198(8) 0.4887(3) 0.32462(18) 0.0350(12) Uani 1 1 d .
C21 C -0.0646(12) 0.8200(4) 0.0739(2) 0.0522(17) Uani 1 1 d .
H21 H -0.0444 0.8762 0.0737 0.063 Uiso 1 1 calc R
C23 C 0.2092(10) 0.5512(3) 0.11195(18) 0.0380(13) Uani 1 1 d .
H23A H 0.2993 0.5184 0.1322 0.046 Uiso 1 1 calc R
H23B H 0.0811 0.5212 0.1070 0.046 Uiso 1 1 calc R
C12 C 0.4773(10) 0.4453(4) 0.3591(2) 0.0448(14) Uani 1 1 d .
H12A H 0.3816 0.4838 0.3728 0.067 Uiso 1 1 calc R
H12B H 0.5580 0.4207 0.3843 0.067 Uiso 1 1 calc R
H12C H 0.4014 0.4038 0.3422 0.067 Uiso 1 1 calc R
C19 C -0.2428(11) 0.7034(5) 0.0464(2) 0.0607(19) Uani 1 1 d .
H19 H -0.3441 0.6799 0.0270 0.073 Uiso 1 1 calc R
C31 C -0.0853(11) 0.1869(3) 0.0670(2) 0.0490(16) Uani 1 1 d .
H31A H -0.2259 0.1979 0.0574 0.073 Uiso 1 1 calc R
H31B H -0.0833 0.1697 0.1000 0.073 Uiso 1 1 calc R
H31C H -0.0287 0.1445 0.0471 0.073 Uiso 1 1 calc R
C20 C -0.2133(10) 0.7863(5) 0.0450(2) 0.061(2) Uani 1 1 d .
H20 H -0.2929 0.8189 0.0247 0.073 Uiso 1 1 calc R
C14 C -0.1546(9) 0.5548(3) 0.1794(2) 0.0353(12) Uani 1 1 d .
H14A H -0.2280 0.5499 0.2093 0.053 Uiso 1 1 calc R
H14B H -0.1119 0.5016 0.1687 0.053 Uiso 1 1 calc R
H14C H -0.2441 0.5790 0.1557 0.053 Uiso 1 1 calc R
C11 C 0.7602(10) 0.5487(4) 0.3497(2) 0.0532(17) Uani 1 1 d .
H11A H 0.8302 0.5817 0.3262 0.080 Uiso 1 1 calc R
H11B H 0.8610 0.5197 0.3685 0.080 Uiso 1 1 calc R
H11C H 0.6787 0.5831 0.3704 0.080 Uiso 1 1 calc R
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
O4 S1 O5 118.3(2)
O4 S1 N2 107.9(2)
O5 S1 N2 105.5(2)
O4 S1 C24 108.3(2)
O5 S1 C24 110.3(2)
N2 S1 C24 105.7(2)
C9 O2 C10 118.8(4)
C25 C24 C29 121.8(5)
C25 C24 S1 118.2(4)
C29 C24 S1 120.0(4)
C9 N1 C1 126.1(4)
C9 N1 C8 124.9(4)
C1 N1 C8 108.5(4)
C29 C28 C27 123.9(5)
C5 C6 C7 120.5(5)
C4 C3 C8 119.2(5)
C4 C3 C2 129.8(5)
C8 C3 C2 110.8(4)
C28 C29 C24 115.9(5)
C28 C29 C32 116.8(5)
C24 C29 C32 127.3(4)
C26 C27 C28 117.6(5)
C26 C27 C31 122.2(5)
C28 C27 C31 120.1(5)
C16 C15 C17 112.0(4)
C16 C15 C23 109.0(4)
C17 C15 C23 110.2(4)
C16 C15 C2 108.2(4)
C17 C15 C2 110.6(4)
C23 C15 C2 106.6(4)
C6 C5 C4 120.6(5)
C3 C8 C7 122.9(5)
C3 C8 N1 110.0(4)
C7 C8 N1 127.1(4)
C23 N2 S1 116.4(3)
O1 C9 O2 127.6(5)
O1 C9 N1 121.8(5)
O2 C9 N1 110.6(4)
C8 C7 C6 117.2(5)
C26 C25 C24 117.4(5)
C26 C25 C30 117.3(5)
C24 C25 C30 125.3(5)
C3 C2 C14 111.7(4)
C3 C2 C1 101.4(4)
C14 C2 C1 107.0(4)
C3 C2 C15 112.4(4)
C14 C2 C15 115.0(4)
C1 C2 C15 108.3(4)
O3 C1 N1 125.4(5)
O3 C1 C2 125.6(5)
N1 C1 C2 109.0(4)
C17 C18 C19 121.5(6)
C27 C26 C25 123.3(5)
C18 C17 C22 116.3(5)
C18 C17 C15 121.7(4)
C22 C17 C15 122.0(5)
C21 C22 C17 121.8(6)
C3 C4 C5 119.6(5)
O2 C10 C12 108.6(4)
O2 C10 C11 111.8(4)
C12 C10 C11 112.3(5)
O2 C10 C13 101.1(4)
C12 C10 C13 110.6(5)
C11 C10 C13 111.9(5)
C20 C21 C22 120.5(6)
N2 C23 C15 111.5(4)
C20 C19 C18 121.2(6)
C21 C20 C19 118.7(6)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O4 1.427(4)
S1 O5 1.427(4)
S1 N2 1.619(4)
S1 C24 1.778(5)
O3 C1 1.205(6)
O2 C9 1.326(6)
O2 C10 1.489(6)
C24 C25 1.405(7)
C24 C29 1.426(7)
N1 C9 1.410(6)
N1 C1 1.414(6)
N1 C8 1.441(6)
O1 C9 1.210(6)
C28 C29 1.392(7)
C28 C27 1.398(8)
C6 C5 1.390(7)
C6 C7 1.399(7)
C3 C4 1.374(7)
C3 C8 1.383(7)
C3 C2 1.507(6)
C29 C32 1.500(7)
C27 C26 1.355(7)
C27 C31 1.499(7)
C15 C16 1.512(7)
C15 C17 1.522(6)
C15 C23 1.540(6)
C15 C2 1.615(7)
C5 C4 1.399(7)
C8 C7 1.395(7)
N2 C23 1.484(6)
C25 C26 1.403(7)
C25 C30 1.492(7)
C2 C14 1.536(7)
C2 C1 1.548(7)
C18 C17 1.375(7)
C18 C19 1.385(8)
C17 C22 1.408(7)
C13 C10 1.530(7)
C22 C21 1.378(8)
C10 C12 1.504(7)
C10 C11 1.506(8)
C21 C20 1.366(10)
C19 C20 1.371(10)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 122225920
