#------------------------------------------------------------------------------
#$Date: 2025-08-18 18:33:07 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301779 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/22/1542267.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_1542267
loop_
_publ_author_name
'Lai, Bo-Nan'
'Qiu, Jian-Feng'
'Zhang, Heng-Xia'
'Nie, Jing'
'Ma, Jun-An'
_publ_section_title
;
 Stereoselective Synthesis of Fused Aziridines via One-Pot Sequential
 Decarboxylative Mannich Reaction and Oxidative C-H Amination of Cyclic
 Imines with β-Ketoacids.
;
_journal_issue                   3
_journal_name_full               'Organic letters'
_journal_page_first              520
_journal_page_last               523
_journal_paper_doi               10.1021/acs.orglett.5b03551
_journal_volume                  18
_journal_year                    2016
_chemical_absolute_configuration rm
_chemical_formula_sum            'C15 H11 N O4 S'
_chemical_formula_weight         301.31
_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                   6.9902(15)
_cell_length_b                   10.327(2)
_cell_length_c                   18.799(4)
_cell_measurement_reflns_used    2925
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.63
_cell_measurement_theta_min      2.93
_cell_volume                     1357.1(5)
_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      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0230
_diffrn_reflns_av_sigmaI/netI    0.0262
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            7660
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.25
_exptl_absorpt_coefficient_mu    0.254
_exptl_absorpt_correction_T_max  0.9463
_exptl_absorpt_correction_T_min  0.9232
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_diffrn    1.475
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.211
_refine_diff_density_min         -0.327
_refine_diff_density_rms         0.058
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.05(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2674
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.0386
_refine_ls_R_factor_gt           0.0342
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0554P)²+0.0288P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0878
_refine_ls_wR_factor_ref         0.0914
_reflns_number_gt                2448
_reflns_number_total             2674
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol5b03551_si_002.cif
_cod_data_source_block           150712a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

'_exptl_absorpt_correction_type' value 'MULTI-SCAN' changed to
'multi-scan' according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

'_exptl_crystal_density_meas' value 'NONE' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 

 Adding full bibliography for 1542267.cif.
;
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               1542267
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -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
S1 S 0.51369(8) 1.05734(5) 0.74691(3) 0.04062(15) Uani 1 1 d .
O1 O 0.7690(3) 1.01965(14) 0.54548(7) 0.0548(4) Uani 1 1 d .
O2 O 0.3304(2) 1.05835(18) 0.71528(9) 0.0590(4) Uani 1 1 d .
O3 O 0.5756(3) 1.16225(15) 0.78907(8) 0.0579(5) Uani 1 1 d .
O4 O 0.5155(2) 0.93002(13) 0.79375(7) 0.0433(3) Uani 1 1 d .
N1 N 0.6772(2) 1.03694(15) 0.68609(8) 0.0372(4) Uani 1 1 d .
C1 C 0.7397(3) 0.7957(2) 0.45970(10) 0.0409(5) Uani 1 1 d .
H1 H 0.7372 0.8746 0.4359 0.049 Uiso 1 1 calc R
C2 C 0.7424(3) 0.6816(2) 0.42193(12) 0.0500(5) Uani 1 1 d .
H2 H 0.7385 0.6840 0.3725 0.060 Uiso 1 1 calc R
C3 C 0.7509(4) 0.5645(2) 0.45605(13) 0.0557(6) Uani 1 1 d .
H3 H 0.7542 0.4880 0.4299 0.067 Uiso 1 1 calc R
C4 C 0.7545(4) 0.5608(2) 0.52898(13) 0.0549(6) Uani 1 1 d .
H4 H 0.7611 0.4815 0.5523 0.066 Uiso 1 1 calc R
C5 C 0.7483(3) 0.6735(2) 0.56804(12) 0.0460(5) Uani 1 1 d .
H5 H 0.7492 0.6698 0.6175 0.055 Uiso 1 1 calc R
C6 C 0.7408(3) 0.79223(19) 0.53387(10) 0.0351(4) Uani 1 1 d .
C7 C 0.7361(3) 0.91637(19) 0.57294(10) 0.0360(4) Uani 1 1 d .
C8 C 0.6918(3) 0.90961(18) 0.65168(10) 0.0338(4) Uani 1 1 d .
H8 H 0.6021 0.8425 0.6673 0.041 Uiso 1 1 calc R
C9 C 0.8415(3) 0.95221(19) 0.70394(10) 0.0372(5) Uani 1 1 d .
H9 H 0.9643 0.9779 0.6831 0.045 Uiso 1 1 calc R
C10 C 0.8527(3) 0.89267(19) 0.77548(11) 0.0389(5) Uani 1 1 d .
C11 C 0.6949(3) 0.88692(19) 0.81956(10) 0.0384(5) Uani 1 1 d .
C12 C 0.7012(4) 0.8364(2) 0.88675(12) 0.0526(6) Uani 1 1 d .
H12 H 0.5933 0.8367 0.9157 0.063 Uiso 1 1 calc R
C13 C 0.8715(4) 0.7852(2) 0.91028(13) 0.0589(7) Uani 1 1 d .
H13 H 0.8788 0.7505 0.9558 0.071 Uiso 1 1 calc R
C14 C 1.0299(4) 0.7846(2) 0.86778(12) 0.0571(7) Uani 1 1 d .
H14 H 1.1428 0.7472 0.8840 0.068 Uiso 1 1 calc R
C15 C 1.0228(3) 0.8395(2) 0.80082(12) 0.0511(6) Uani 1 1 d .
H15 H 1.1319 0.8409 0.7725 0.061 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
O3 S1 O2 120.61(11)
O3 S1 O4 108.85(9)
O2 S1 O4 104.32(9)
O3 S1 N1 106.15(10)
O2 S1 N1 109.99(10)
O4 S1 N1 106.10(8)
C11 O4 S1 117.29(12)
C8 N1 C9 61.16(12)
C8 N1 S1 118.23(13)
C9 N1 S1 117.44(13)
C2 C1 C6 119.6(2)
C2 C1 H1 120.2
C6 C1 H1 120.2
C3 C2 C1 121.0(2)
C3 C2 H2 119.5
C1 C2 H2 119.5
C2 C3 C4 119.5(2)
C2 C3 H3 120.2
C4 C3 H3 120.2
C3 C4 C5 120.6(2)
C3 C4 H4 119.7
C5 C4 H4 119.7
C4 C5 C6 120.1(2)
C4 C5 H5 119.9
C6 C5 H5 119.9
C5 C6 C1 119.1(2)
C5 C6 C7 122.57(17)
C1 C6 C7 118.33(19)
O1 C7 C6 123.34(17)
O1 C7 C8 119.87(18)
C6 C7 C8 116.78(16)
N1 C8 C9 59.85(12)
N1 C8 C7 113.80(16)
C9 C8 C7 118.92(17)
N1 C8 H8 117.2
C9 C8 H8 117.2
C7 C8 H8 117.2
C10 C9 N1 119.45(16)
C10 C9 C8 120.63(17)
N1 C9 C8 58.99(12)
C10 C9 H9 115.4
N1 C9 H9 115.4
C8 C9 H9 115.4
C11 C10 C15 117.34(19)
C11 C10 C9 121.37(18)
C15 C10 C9 121.29(19)
C12 C11 C10 123.0(2)
C12 C11 O4 117.7(2)
C10 C11 O4 119.23(17)
C11 C12 C13 118.1(2)
C11 C12 H12 120.9
C13 C12 H12 120.9
C14 C13 C12 121.0(2)
C14 C13 H13 119.5
C12 C13 H13 119.5
C13 C14 C15 120.1(2)
C13 C14 H14 119.9
C15 C14 H14 119.9
C14 C15 C10 120.2(2)
C14 C15 H15 119.9
C10 C15 H15 119.9
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O3 1.4104(17)
S1 O2 1.4127(17)
S1 O4 1.5826(14)
S1 N1 1.6305(16)
O1 C7 1.207(2)
O4 C11 1.417(3)
N1 C8 1.469(2)
N1 C9 1.482(3)
C1 C2 1.376(3)
C1 C6 1.395(3)
C1 H1 0.9300
C2 C3 1.371(3)
C2 H2 0.9300
C3 C4 1.372(3)
C3 H3 0.9300
C4 C5 1.376(3)
C4 H4 0.9300
C5 C6 1.386(3)
C5 H5 0.9300
C6 C7 1.478(3)
C7 C8 1.514(3)
C8 C9 1.501(3)
C8 H8 0.9800
C9 C10 1.481(3)
C9 H9 0.9800
C10 C11 1.381(3)
C10 C15 1.394(3)
C11 C12 1.367(3)
C12 C13 1.376(4)
C12 H12 0.9300
C13 C14 1.366(4)
C13 H13 0.9300
C14 C15 1.381(3)
C14 H14 0.9300
C15 H15 0.9300
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
O3 S1 O4 C11 -63.83(16)
O2 S1 O4 C11 166.19(14)
N1 S1 O4 C11 50.03(15)
O3 S1 N1 C8 157.57(14)
O2 S1 N1 C8 -70.40(16)
O4 S1 N1 C8 41.87(16)
O3 S1 N1 C9 87.34(16)
O2 S1 N1 C9 -140.64(15)
O4 S1 N1 C9 -28.37(16)
C6 C1 C2 C3 -1.6(3)
C1 C2 C3 C4 0.8(4)
C2 C3 C4 C5 0.5(4)
C3 C4 C5 C6 -0.8(4)
C4 C5 C6 C1 0.0(3)
C4 C5 C6 C7 -179.3(2)
C2 C1 C6 C5 1.2(3)
C2 C1 C6 C7 -179.45(19)
C5 C6 C7 O1 164.2(2)
C1 C6 C7 O1 -15.1(3)
C5 C6 C7 C8 -14.3(3)
C1 C6 C7 C8 166.36(19)
S1 N1 C8 C9 -107.55(16)
C9 N1 C8 C7 -110.80(19)
S1 N1 C8 C7 141.65(15)
O1 C7 C8 N1 5.1(3)
C6 C7 C8 N1 -176.28(16)
O1 C7 C8 C9 -62.3(3)
C6 C7 C8 C9 116.3(2)
C8 N1 C9 C10 -110.08(19)
S1 N1 C9 C10 -1.3(2)
S1 N1 C9 C8 108.81(15)
N1 C8 C9 C10 108.11(19)
C7 C8 C9 C10 -149.64(18)
C7 C8 C9 N1 102.25(19)
N1 C9 C10 C11 16.3(3)
C8 C9 C10 C11 -53.0(3)
N1 C9 C10 C15 -164.11(19)
C8 C9 C10 C15 126.6(2)
C15 C10 C11 C12 2.5(3)
C9 C10 C11 C12 -177.9(2)
C15 C10 C11 O4 -174.79(18)
C9 C10 C11 O4 4.8(3)
S1 O4 C11 C12 141.77(16)
S1 O4 C11 C10 -40.8(2)
C10 C11 C12 C13 -2.3(3)
O4 C11 C12 C13 175.09(19)
C11 C12 C13 C14 -0.1(3)
C12 C13 C14 C15 2.0(4)
C13 C14 C15 C10 -1.7(3)
C11 C10 C15 C14 -0.5(3)
C9 C10 C15 C14 179.91(19)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 132559157
