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#$Date: 2025-08-20 12:41:31 +0300 (Wed, 20 Aug 2025) $
#$Revision: 301828 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/07/4030768.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_4030768
loop_
_publ_author_name
'Silva, Saúl'
'Rodrigues, Paula'
'Bento, Isabel'
'Maycock, Christopher D.'
_publ_section_title
;
 The aza-wharton reaction: syntheses of cyclic allylic amines and vicinal
 hydroxyamines from the respective acylaziridines.
;
_journal_issue                   6
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              3067
_journal_page_last               3074
_journal_paper_doi               10.1021/jo5029387
_journal_volume                  80
_journal_year                    2015
_chemical_formula_sum            'C13 H15 N O'
_chemical_formula_weight         201.26
_space_group_IT_number           4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_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                 105.678(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.1102(14)
_cell_length_b                   5.2791(9)
_cell_length_c                   13.309(2)
_cell_measurement_temperature    296(2)
_cell_volume                     548.62(16)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0198
_diffrn_reflns_av_sigmaI/netI    0.0312
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            6471
_diffrn_reflns_theta_full        31.51
_diffrn_reflns_theta_max         31.51
_diffrn_reflns_theta_min         1.59
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.9699
_exptl_absorpt_correction_T_min  0.9000
_exptl_crystal_density_diffrn    1.218
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             216
_exptl_crystal_size_max          1.40
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.40
_refine_diff_density_max         0.290
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         3384
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0448
_refine_ls_R_factor_gt           0.0385
_refine_ls_shift/su_max          1.626
_refine_ls_shift/su_mean         0.047
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0606P)²+0.0616P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0976
_refine_ls_wR_factor_ref         0.1017
_reflns_number_gt                3071
_reflns_number_total             3384
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo5029387_si_002.cif
_cod_data_source_block           shelxl
_cod_depositor_comments
'Adding full bibliography for 4030767--4030768.cif.'
_cod_original_cell_volume        548.60(16)
_cod_database_code               4030768
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, 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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O -0.27057(13) 0.5771(3) -0.04185(8) 0.0364(3) Uani 1 1 d .
N1 N -0.03244(12) 0.74090(19) 0.20529(7) 0.01706(18) Uani 1 1 d .
C13 C -0.32699(15) 0.8907(3) 0.18631(10) 0.0235(2) Uani 1 1 d .
H4 H -0.4036 1.0335 0.1644 0.028 Uiso 1 1 calc R
H15 H -0.3317 0.8376 0.2552 0.028 Uiso 1 1 calc R
C1 C -0.37617(14) 0.6713(3) 0.10799(9) 0.0218(2) Uani 1 1 d .
H1 H -0.3685 0.5108 0.1445 0.026 Uiso 1 1 calc R
H3 H -0.4924 0.6925 0.0646 0.026 Uiso 1 1 calc R
C2 C -0.25056(14) 0.6780(3) 0.04174(9) 0.0214(2) Uani 1 1 d .
C3 C -0.10160(14) 0.8367(2) 0.09642(9) 0.0202(2) Uani 1 1 d .
H5 H -0.0280 0.9195 0.0587 0.024 Uiso 1 1 calc R
C4 C 0.15176(13) 0.7980(2) 0.24799(8) 0.0171(2) Uani 1 1 d .
H13 H 0.1773 0.9618 0.2209 0.020 Uiso 1 1 calc R
C5 C 0.19373(12) 0.8108(2) 0.36548(8) 0.0158(2) Uani 1 1 d .
C6 C 0.30234(15) 0.9985(2) 0.41960(9) 0.0219(2) Uani 1 1 d .
H9 H 0.3457 1.1197 0.3829 0.026 Uiso 1 1 calc R
C7 C 0.34676(17) 1.0067(3) 0.52810(10) 0.0261(3) Uani 1 1 d .
H8 H 0.4201 1.1324 0.5635 0.031 Uiso 1 1 calc R
C8 C 0.28220(16) 0.8287(3) 0.58312(9) 0.0251(2) Uani 1 1 d .
H2 H 0.3116 0.8345 0.6556 0.030 Uiso 1 1 calc R
C9 C -0.14539(15) 0.9606(2) 0.18664(9) 0.0207(2) Uani 1 1 d .
H14 H -0.1000 1.1289 0.2101 0.025 Uiso 1 1 calc R
C10 C 0.17330(16) 0.6409(3) 0.53016(9) 0.0240(2) Uani 1 1 d .
H7 H 0.1295 0.5209 0.5672 0.029 Uiso 1 1 calc R
C11 C 0.12954(15) 0.6318(2) 0.42180(9) 0.0203(2) Uani 1 1 d .
H6 H 0.0568 0.5052 0.3866 0.024 Uiso 1 1 calc R
C12 C 0.25290(15) 0.5909(3) 0.21156(10) 0.0256(3) Uani 1 1 d .
H12 H 0.2279 0.5948 0.1368 0.038 Uiso 1 1 calc R
H10 H 0.2214 0.4289 0.2334 0.038 Uiso 1 1 calc R
H11 H 0.3732 0.6185 0.2415 0.038 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C9 N1 C4 115.24(9)
C9 N1 C3 60.74(8)
C4 N1 C3 112.29(8)
C9 C13 C1 105.01(10)
C9 C13 H4 110.7
C1 C13 H4 110.7
C9 C13 H15 110.7
C1 C13 H15 110.7
H4 C13 H15 108.8
C2 C1 C13 106.53(10)
C2 C1 H1 110.4
C13 C1 H1 110.4
C2 C1 H3 110.4
C13 C1 H3 110.4
H1 C1 H3 108.6
O1 C2 C3 126.13(11)
O1 C2 C1 125.62(11)
C3 C2 C1 108.22(10)
C2 C3 C9 107.57(10)
C2 C3 N1 109.03(9)
C9 C3 N1 58.42(7)
C2 C3 H5 121.8
C9 C3 H5 121.8
N1 C3 H5 121.8
N1 C4 C5 109.20(8)
N1 C4 C12 107.84(10)
C5 C4 C12 111.83(9)
N1 C4 H13 109.3
C5 C4 H13 109.3
C12 C4 H13 109.3
C6 C5 C11 118.79(10)
C6 C5 C4 120.16(10)
C11 C5 C4 121.02(10)
C5 C6 C7 120.66(11)
C5 C6 H9 119.7
C7 C6 H9 119.7
C8 C7 C6 120.06(12)
C8 C7 H8 120.0
C6 C7 H8 120.0
C7 C8 C10 119.90(11)
C7 C8 H2 120.1
C10 C8 H2 120.0
N1 C9 C3 60.84(8)
N1 C9 C13 111.85(10)
C3 C9 C13 109.46(10)
N1 C9 H14 120.2
C3 C9 H14 120.2
C13 C9 H14 120.2
C8 C10 C11 120.06(12)
C8 C10 H7 120.0
C11 C10 H7 120.0
C10 C11 C5 120.52(11)
C10 C11 H6 119.7
C5 C11 H6 119.7
C4 C12 H12 109.5
C4 C12 H10 109.5
H12 C12 H10 109.5
C4 C12 H11 109.5
H12 C12 H11 109.5
H10 C12 H11 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C2 1.2042(15)
N1 C9 1.4569(15)
N1 C4 1.4788(14)
N1 C3 1.4935(14)
C13 C9 1.5172(17)
C13 C1 1.5370(18)
C13 H4 0.9700
C13 H15 0.9700
C1 C2 1.5172(16)
C1 H1 0.9700
C1 H3 0.9700
C2 C3 1.4886(16)
C3 C9 1.4919(17)
C3 H5 0.9800
C4 C5 1.5092(15)
C4 C12 1.5226(17)
C4 H13 0.9800
C5 C6 1.3905(16)
C5 C11 1.3915(15)
C6 C7 1.3912(17)
C6 H9 0.9300
C7 C8 1.379(2)
C7 H8 0.9300
C8 C10 1.3868(19)
C8 H2 0.9300
C9 H14 0.9800
C10 C11 1.3898(16)
C10 H7 0.9300
C11 H6 0.9300
C12 H12 0.9600
C12 H10 0.9600
C12 H11 0.9600
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
C9 C13 C1 C2 -17.84(13)
C13 C1 C2 O1 -161.65(14)
C13 C1 C2 C3 16.69(14)
O1 C2 C3 C9 169.63(14)
C1 C2 C3 C9 -8.70(14)
O1 C2 C3 N1 -128.53(15)
C1 C2 C3 N1 53.14(13)
C9 N1 C3 C2 -99.37(11)
C4 N1 C3 C2 153.25(10)
C4 N1 C3 C9 -107.37(10)
C9 N1 C4 C5 87.06(11)
C3 N1 C4 C5 154.05(9)
C9 N1 C4 C12 -151.23(10)
C3 N1 C4 C12 -84.23(11)
N1 C4 C5 C6 -138.54(10)
C12 C4 C5 C6 102.19(13)
N1 C4 C5 C11 43.50(14)
C12 C4 C5 C11 -75.77(13)
C11 C5 C6 C7 0.29(18)
C4 C5 C6 C7 -177.71(11)
C5 C6 C7 C8 -0.40(19)
C6 C7 C8 C10 0.2(2)
C4 N1 C9 C3 102.50(10)
C4 N1 C9 C13 -156.70(9)
C3 N1 C9 C13 100.80(10)
C2 C3 C9 N1 101.93(10)
C2 C3 C9 C13 -2.83(14)
N1 C3 C9 C13 -104.76(11)
C1 C13 C9 N1 -52.58(12)
C1 C13 C9 C3 12.90(13)
C7 C8 C10 C11 0.11(19)
C8 C10 C11 C5 -0.22(18)
C6 C5 C11 C10 0.02(17)
C4 C5 C11 C10 178.01(11)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139094155
