#------------------------------------------------------------------------------
#$Date: 2025-06-17 20:57:51 +0300 (Tue, 17 Jun 2025) $
#$Revision: 300101 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/31/1553132.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_1553132
loop_
_publ_author_name
'Ye, Jian-Liang'
'Zhang, Yu-Feng'
'Liu, Yang'
'Zhang, Jin-Yuan'
'Ruan, Yuan-Ping'
'Huang, Pei-Qiang'
_publ_section_title
;
 Studies on the asymmetric synthesis of pandamarilactonines: an unexpected
 syn-selective vinylogous Mannich reaction of N-tert-butanesulfinimines
;
_journal_issue                   6
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              697
_journal_paper_doi               10.1039/C5QO00098J
_journal_volume                  2
_journal_year                    2015
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C13 H23 N O3 S'
_chemical_formula_sum            'C13 H23 N O3 S'
_chemical_formula_weight         273.39
_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'
_symmetry_Int_Tables_number      4
_atom_sites_solution_primary     direct
_audit_creation_date             2015-02-04
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2015-03-25 deposited with the CCDC.
2015-04-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.531(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.291(2)
_cell_length_b                   5.9808(12)
_cell_length_c                   12.068(2)
_cell_measurement_reflns_used    4213
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      28.25
_cell_measurement_theta_min      2.35
_cell_volume                     722.1(2)
_computing_cell_refinement       'SAINT v6.28A (Bruker, 2002)'
_computing_data_reduction        'SAINT v6.28A (Bruker, 2002)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.9880
_diffrn_measured_fraction_theta_max 0.9880
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0142
_diffrn_reflns_av_unetI/netI     0.0234
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            4174
_diffrn_reflns_theta_full        26.0000
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.74
_exptl_absorpt_coefficient_mu    0.225
_exptl_absorpt_correction_T_min  0.845984
_exptl_absorpt_process_details
;
SADABS v.2.03 (Bruker,200?) was used for absorption correction.
R(int) was 0.0532 before and 0.0281 after correction.
The Ratio of minimum to maximum transmission is 0.8460.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_density_diffrn    1.2573
_exptl_crystal_description       pillar
_exptl_crystal_F_000             296.3836
_refine_diff_density_max         0.3993
_refine_diff_density_min         -0.3000
_refine_diff_density_rms         0.0707
_refine_ls_abs_structure_details
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   0.06(6)
_refine_ls_d_res_high            0.8107
_refine_ls_d_res_low             11.7328
_refine_ls_goodness_of_fit_ref   1.0660
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    34
_refine_ls_number_parameters     167
_refine_ls_number_reflns         2522
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0660
_refine_ls_R_factor_all          0.0315
_refine_ls_R_factor_gt           0.0314
_refine_ls_shift/su_max          0.0014
_refine_ls_shift/su_mean         0.0002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0670P)²+0.0874P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0880
_refine_ls_wR_factor_ref         0.0880
_reflns_Friedel_coverage         0.784
_reflns_limit_h_max              12
_reflns_limit_h_min              -12
_reflns_limit_k_max              7
_reflns_limit_k_min              -7
_reflns_limit_l_max              14
_reflns_limit_l_min              -14
_reflns_number_gt                2517
_reflns_number_total             2522
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            c5qo00098j2.cif
_cod_data_source_block           y0121m
_cod_depositor_comments
;

2025-06-17
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C2.889 H5.111 N0.222 O0.667 S0.222'
_cod_original_formula_weight         60.76
_cod_original_formula_moiety         '0.22(C13 H23 N O3 S)'
_cod_original_formula_units_Z            9
_cod_original_cell_volume        722.1(3)
_cod_original_sg_symbol_Hall     ' P 2yb'
_cod_database_code               1553132
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C5(H5), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9a,H9b), C16(H16a,H16b)
2.c Aromatic/amide H refined with riding coordinates:
 N3(H3), C10(H10)
2.d Idealised Me refined as rotating group:
 C6(H6a,H6b,H6c), C8(H8a,H8b,H8c), C13(H13a,H13b,H13c), C15(H15a,H15b,H15c),
 C17(H17a,H17b,H17c)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -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_refinement_flags_posn
S1 S -0.619319(3) -0.037804(3) -0.447119(3) 0.02109(8) Uani 1.000000 .
O0AA O -0.572465(3) 0.007992(3) -0.553855(3) 0.02656(15) Uani 1.000000 .
N3 N -0.526355(3) 0.106118(3) -0.338996(3) 0.02441(16) Uani 1.000000 .
H3 H -0.543894(3) 0.242958(3) -0.326131(3) 0.02929(19) Uiso 1.000000 R
O4 O -0.695603(3) 0.038524(3) -0.034600(3) 0.04299(16) Uani 1.000000 .
C5 C -0.411560(3) -0.014557(3) -0.266010(3) 0.02417(16) Uani 1.000000 .
H5 H -0.379868(3) -0.126468(3) -0.312867(3) 0.02901(19) Uiso 1.000000 R
C6 C -0.837635(3) 0.060333(3) -0.365468(3) 0.03509(18) Uani 1.000000 .
H6a H -0.845088(4) -0.099262(3) -0.361120(4) 0.0526(3) Uiso 1.000000 GR
H6b H -0.780922(4) 0.115378(4) -0.296074(3) 0.0526(3) Uiso 1.000000 GR
H6c H -0.924674(4) 0.126518(4) -0.376139(4) 0.0526(3) Uiso 1.000000 GR
C7 C -0.627934(3) -0.060557(3) -0.087758(3) 0.02877(17) Uani 1.000000 .
C8 C -0.755765(3) 0.371087(3) -0.472948(3) 0.02914(18) Uani 1.000000 .
H8a H -0.711083(4) 0.426971(3) -0.399311(3) 0.0437(3) Uiso 1.000000 GR
H8b H -0.701826(4) 0.399655(3) -0.526434(4) 0.0437(3) Uiso 1.000000 GR
H8c H -0.840474(3) 0.444722(3) -0.497859(4) 0.0437(3) Uiso 1.000000 GR
C9 C -0.298191(3) 0.152302(3) -0.221973(3) 0.03045(18) Uani 1.000000 .
H9a H -0.289150(3) 0.248743(3) -0.284358(3) 0.0365(2) Uiso 1.000000 R
H9b H -0.322358(3) 0.245618(3) -0.164181(3) 0.0365(2) Uiso 1.000000 R
C10 C -0.553140(3) -0.316026(3) -0.195732(3) 0.02859(18) Uani 1.000000 .
H10 H -0.546278(3) -0.439792(3) -0.240668(3) 0.0343(2) Uiso 1.000000 R
C11 C -0.777764(3) 0.121130(3) -0.465419(3) 0.02421(17) Uani 1.000000 .
C12 C -0.451543(3) -0.134792(3) -0.167112(3) 0.02632(17) Uani 1.000000 .
H12 H -0.370590(3) -0.198077(3) -0.117699(3) 0.0316(2) Uiso 1.000000 R
C13 C -0.864309(3) 0.032529(3) -0.577692(3) 0.03438(18) Uani 1.000000 .
H13a H -0.822239(4) 0.066336(4) -0.638803(3) 0.0516(3) Uiso 1.000000 GR
H13b H -0.874246(4) -0.126456(3) -0.572453(4) 0.0516(3) Uiso 1.000000 GR
H13c H -0.950697(4) 0.102162(4) -0.592203(4) 0.0516(3) Uiso 1.000000 GR
C14 C -0.654529(3) -0.276458(3) -0.148332(3) 0.02841(17) Uani 1.000000 .
C15 C -0.776904(3) -0.408454(3) -0.146870(3) 0.04210(19) Uani 1.000000 .
H15a H -0.760317(4) -0.502075(4) -0.080423(4) 0.0632(3) Uiso 1.000000 GR
H15b H -0.849408(4) -0.308465(3) -0.145236(4) 0.0632(3) Uiso 1.000000 GR
H15c H -0.799837(4) -0.499871(4) -0.214009(4) 0.0632(3) Uiso 1.000000 GR
C16 C -0.163941(3) 0.043425(3) -0.171680(3) 0.04054(19) Uani 1.000000 .
H16a H -0.172713(3) -0.056536(3) -0.110552(3) 0.0487(2) Uiso 1.000000 R
H16b H -0.137147(3) -0.044999(3) -0.229949(3) 0.0487(2) Uiso 1.000000 R
C17 C -0.056158(3) 0.216980(3) -0.125456(3) 0.0512(2) Uani 1.000000 .
H17a H -0.052769(4) 0.324081(4) -0.183965(4) 0.0768(3) Uiso 1.000000 GR
H17b H -0.076838(4) 0.292049(4) -0.061389(4) 0.0768(3) Uiso 1.000000 GR
H17c H 0.028928(3) 0.143976(3) -0.101937(4) 0.0768(3) Uiso 1.000000 GR
O1 O -0.508925(3) 0.021185(3) -0.100489(3) 0.03143(15) Uani 1.000000 .
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
S 0.12424 0.12443 6.90530 5.20340 1.43790 1.58630 1.46790 22.21510 0.25360
56.17200 0.866900026798
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
N3 S1 O0AA 109.673(3)
C11 S1 O0AA 104.711(2)
C11 S1 N3 98.985(2)
C5 N3 S1 116.413(2)
C9 C5 N3 108.939(2)
C12 C5 N3 111.672(3)
C12 C5 C9 110.939(3)
C14 C7 O4 128.973(3)
O1 C7 O4 122.022(3)
O1 C7 C14 109.004(3)
C16 C9 C5 113.9947(19)
C14 C10 C12 110.568(3)
C6 C11 S1 106.908(2)
C8 C11 S1 111.868(3)
C8 C11 C6 112.123(3)
C13 C11 S1 103.947(3)
C13 C11 C6 111.050(3)
C13 C11 C8 110.601(3)
C10 C12 C5 117.613(3)
O1 C12 C5 110.497(2)
O1 C12 C10 104.052(3)
C10 C14 C7 107.256(3)
C15 C14 C7 121.094(3)
C15 C14 C10 131.643(3)
C17 C16 C9 111.6938(19)
C12 O1 C7 109.073(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O0AA 1.5024(3)
S1 N3 1.6657(2)
S1 C11 1.8554(3)
N3 C5 1.4850(2)
O4 C7 1.20691(15)
C5 C9 1.5327(2)
C5 C12 1.5299(2)
C6 C11 1.5213(2)
C7 C14 1.4775(2)
C7 O1 1.3604(2)
C8 C11 1.5179(3)
C9 C16 1.5194(2)
C10 C12 1.4894(2)
C10 C14 1.3233(2)
C11 C13 1.5314(2)
C12 O1 1.44482(18)
C14 C15 1.4899(2)
C16 C17 1.5262(2)
