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#$Date: 2025-08-20 19:06:18 +0300 (Wed, 20 Aug 2025) $
#$Revision: 301834 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/12/13/4121371.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_4121371
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_formula_sum            'C20 H24 N2'
_chemical_formula_weight         292.41
_space_group_IT_number           146
_symmetry_cell_setting           rhombohedral
_symmetry_space_group_name_Hall  'R 3'
_symmetry_space_group_name_H-M   'R 3 :H'
_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                120.00
_cell_formula_units_Z            9
_cell_length_a                   21.290(6)
_cell_length_b                   21.290(6)
_cell_length_c                   9.790(4)
_cell_measurement_reflns_used    2816
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      28.28
_cell_measurement_theta_min      2.35
_cell_volume                     3843(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      123(2)
_diffrn_detector_area_resol_mean 8.366
_diffrn_measured_fraction_theta_full 0.876
_diffrn_measured_fraction_theta_max 0.876
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0528
_diffrn_reflns_av_sigmaI/netI    0.0908
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7069
_diffrn_reflns_theta_full        28.34
_diffrn_reflns_theta_max         28.34
_diffrn_reflns_theta_min         1.91
_exptl_absorpt_coefficient_mu    0.067
_exptl_absorpt_correction_T_max  0.9934
_exptl_absorpt_correction_T_min  0.9803
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.137
_exptl_crystal_description       block
_exptl_crystal_F_000             1422
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -1(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.169
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         3315
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.169
_refine_ls_R_factor_all          0.0973
_refine_ls_R_factor_gt           0.0748
_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)+(0.0626P)²+2.9241P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1857
_refine_ls_wR_factor_ref         0.1931
_reflns_number_gt                2401
_reflns_number_total             3315
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja411647x_si_006.cif
_cod_data_source_block           3427and
_cod_original_sg_symbol_H-M      'R 3'
_cod_database_code               4121371
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
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
C3 C 0.5434(2) 0.7204(2) 0.2925(4) 0.0311(9) Uani 1 1 d .
C16 C 0.7600(2) 0.9432(2) 0.3313(4) 0.0325(9) Uani 1 1 d .
H16 H 0.7776 0.9417 0.4197 0.039 Uiso 1 1 calc R
C20 C 0.6641(2) 0.9023(2) 0.1708(4) 0.0357(9) Uani 1 1 d .
H20 H 0.6147 0.8714 0.1465 0.043 Uiso 1 1 calc R
C15 C 0.6875(2) 0.89797(19) 0.3012(4) 0.0276(8) Uani 1 1 d .
C11 C 0.63397(19) 0.84547(18) 0.4041(4) 0.0249(8) Uani 1 1 d .
C1 C 0.5849(2) 0.7291(2) 0.5227(5) 0.0369(10) Uani 1 1 d .
H1 H 0.6042 0.6960 0.5446 0.044 Uiso 1 1 calc R
C2 C 0.61078(19) 0.76313(18) 0.3787(4) 0.0261(7) Uani 1 1 d .
N2 N 0.61206(19) 0.7882(2) 0.6190(4) 0.0341(8) Uani 1 1 d .
C8 C 0.4845(2) 0.6770(2) 0.3794(6) 0.0420(11) Uani 1 1 d .
C10 C 0.6642(2) 0.8546(2) 0.5479(4) 0.0304(8) Uani 1 1 d .
H10A H 0.7130 0.8594 0.5465 0.036 Uiso 1 1 calc R
H10B H 0.6677 0.8979 0.5925 0.036 Uiso 1 1 calc R
C19 C 0.7122(3) 0.9514(3) 0.0754(5) 0.0416(10) Uani 1 1 d .
H19 H 0.6953 0.9545 -0.0128 0.050 Uiso 1 1 calc R
C14 C 0.56676(19) 0.8553(2) 0.4084(4) 0.0279(8) Uani 1 1 d .
H14A H 0.5818 0.9054 0.4342 0.042 Uiso 1 1 calc R
H14B H 0.5320 0.8219 0.4756 0.042 Uiso 1 1 calc R
H14C H 0.5439 0.8450 0.3180 0.042 Uiso 1 1 calc R
C13 C 0.6739(2) 0.7555(2) 0.3261(5) 0.0315(9) Uani 1 1 d .
H13A H 0.6605 0.7043 0.3269 0.047 Uiso 1 1 calc R
H13B H 0.7163 0.7832 0.3849 0.047 Uiso 1 1 calc R
H13C H 0.6857 0.7742 0.2325 0.047 Uiso 1 1 calc R
C17 C 0.8074(2) 0.9907(2) 0.2346(5) 0.0363(9) Uani 1 1 d .
H17 H 0.8572 1.0207 0.2569 0.044 Uiso 1 1 calc R
C18 C 0.7835(3) 0.9951(2) 0.1081(5) 0.0409(10) Uani 1 1 d .
H18 H 0.8163 1.0283 0.0428 0.049 Uiso 1 1 calc R
N1 N 0.5062(2) 0.6881(2) 0.5141(5) 0.0495(11) Uani 1 1 d .
C4 C 0.5342(2) 0.7174(2) 0.1548(5) 0.0371(10) Uani 1 1 d .
H4 H 0.5740 0.7459 0.0961 0.045 Uiso 1 1 calc R
C12 C 0.6412(3) 0.7780(3) 0.7465(5) 0.0496(12) Uani 1 1 d .
H12A H 0.6049 0.7329 0.7902 0.074 Uiso 1 1 calc R
H12B H 0.6533 0.8190 0.8076 0.074 Uiso 1 1 calc R
H12C H 0.6850 0.7754 0.7275 0.074 Uiso 1 1 calc R
C6 C 0.4082(2) 0.6312(3) 0.1864(7) 0.0540(15) Uani 1 1 d .
H6 H 0.3615 0.6010 0.1483 0.065 Uiso 1 1 calc R
C7 C 0.4163(2) 0.6326(2) 0.3258(7) 0.0509(14) Uani 1 1 d .
H7 H 0.3761 0.6039 0.3836 0.061 Uiso 1 1 calc R
C5 C 0.4648(3) 0.6717(2) 0.1009(6) 0.0476(12) Uani 1 1 d .
H5 H 0.4574 0.6689 0.0049 0.057 Uiso 1 1 calc R
C9 C 0.4651(4) 0.6363(3) 0.6205(8) 0.077(2) Uani 1 1 d .
H9A H 0.4132 0.6129 0.5992 0.115 Uiso 1 1 calc R
H9B H 0.4744 0.6615 0.7083 0.115 Uiso 1 1 calc R
H9C H 0.4798 0.5995 0.6258 0.115 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C4 C3 C8 120.4(4)
C4 C3 C2 130.7(4)
C8 C3 C2 108.8(4)
C15 C16 C17 121.0(4)
C15 C20 C19 120.7(4)
C16 C15 C20 117.5(4)
C16 C15 C11 122.7(3)
C20 C15 C11 119.8(3)
C15 C11 C10 114.0(3)
C15 C11 C14 108.9(3)
C10 C11 C14 108.6(3)
C15 C11 C2 114.5(3)
C10 C11 C2 99.4(3)
C14 C11 C2 110.9(3)
N2 C1 N1 113.6(4)
N2 C1 C2 107.0(3)
N1 C1 C2 105.1(4)
C3 C2 C13 111.7(3)
C3 C2 C1 102.5(3)
C13 C2 C1 112.6(3)
C3 C2 C11 115.4(3)
C13 C2 C11 111.6(3)
C1 C2 C11 102.4(3)
C1 N2 C12 116.5(4)
C1 N2 C10 108.1(3)
C12 N2 C10 112.1(4)
N1 C8 C7 129.0(5)
N1 C8 C3 110.6(4)
C7 C8 C3 120.4(5)
N2 C10 C11 104.4(3)
C18 C19 C20 120.3(4)
C18 C17 C16 120.8(4)
C17 C18 C19 119.6(4)
C8 N1 C9 122.2(5)
C8 N1 C1 110.2(4)
C9 N1 C1 119.4(5)
C3 C4 C5 118.9(5)
C5 C6 C7 122.4(4)
C6 C7 C8 118.0(5)
C6 C5 C4 119.9(5)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C3 C4 1.359(6)
C3 C8 1.412(6)
C3 C2 1.513(5)
C16 C15 1.381(5)
C16 C17 1.385(6)
C20 C15 1.391(6)
C20 C19 1.395(6)
C15 C11 1.513(5)
C11 C10 1.520(6)
C11 C14 1.547(5)
C11 C2 1.585(5)
C1 N2 1.441(6)
C1 N1 1.454(6)
C1 C2 1.556(6)
C2 C13 1.522(5)
N2 C12 1.457(6)
N2 C10 1.465(5)
C8 N1 1.379(7)
C8 C7 1.380(7)
C19 C18 1.364(7)
C17 C18 1.359(7)
N1 C9 1.450(7)
C4 C5 1.403(6)
C6 C5 1.363(8)
C6 C7 1.374(8)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139122931
