#------------------------------------------------------------------------------
#$Date: 2023-08-03 03:47:52 +0300 (Thu, 03 Aug 2023) $
#$Revision: 285434 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/95/7159514.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_7159514
loop_
_publ_author_name
'García-Castro, Miguel'
'Moya-Utrera, Federico'
'Sarabia, Francisco'
_publ_section_title
;
 Transition metal-free [2,3]-sigmatropic rearrangement in the reaction of
 sulfur ylides with allenoates.
;
_journal_issue                   30
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              6096
_journal_page_last               6102
_journal_paper_doi               10.1039/d3ob00657c
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         'C16 H29 N O3 S'
_chemical_formula_sum            'C16 H29 N O3 S'
_chemical_formula_weight         315.46
_chemical_name_systematic
'ethyl (E)-3-(2-(dimethylamino)-2-oxoethyl)-5,5-dimethyl-4-((methylthio)methyl)hex-2-enoate'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2023-03-30 deposited with the CCDC.	2023-06-07 downloaded from the CCDC.
;
_cell_angle_alpha                104.564(4)
_cell_angle_beta                 99.048(3)
_cell_angle_gamma                94.974(4)
_cell_formula_units_Z            2
_cell_length_a                   7.4240(3)
_cell_length_b                   8.9236(4)
_cell_length_c                   14.0704(6)
_cell_measurement_reflns_used    8196
_cell_measurement_temperature    160(2)
_cell_measurement_theta_max      73.0220
_cell_measurement_theta_min      3.2410
_cell_volume                     883.16(7)
_computing_cell_refinement
'CrysAlisPro, Version 1.171.42.57a (Rigaku Oxford Diffraction, 2022)'
_computing_data_collection
'CrysAlisPro, Version 1.171.42.57a (Rigaku Oxford Diffraction, 2022)'
_computing_data_reduction
'CrysAlisPro, Version 1.171.42.57a (Rigaku Oxford Diffraction, 2022)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  'SHELXL-2018 and PLATON (Spek, 2015)'
_computing_structure_refinement  'SHELXL-2018 (Sheldrick, 2015b)'
_computing_structure_solution    'SHELXT-2018 (Sheldrick, 2015a)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      160(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 10.3801
_diffrn_detector_type            'Atlas CCD area detector on a \k goniostat'
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device       'four-circle κ-geometry diffractometer'
_diffrn_measurement_device_type
'Oxford Diffraction SuperNova, dual radiation diffractometer'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0466
_diffrn_reflns_av_unetI/netI     0.0370
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            12288
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.140
_diffrn_reflns_theta_min         3.303
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray source'
_exptl_absorpt_coefficient_mu    1.701
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.637
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model 
plus an empirical absorption correction using spherical harmonics, 
implemented in the SCALE3 ABSPACK scaling algorithm.
CrysAlisPro, Version 1.171.42.57a (Rigaku Oxford Diffraction, 2022)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.186
_exptl_crystal_description       plate
_exptl_crystal_F_000             344
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.609
_refine_diff_density_min         -0.549
_refine_diff_density_rms         0.078
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     197
_refine_ls_number_reflns         3445
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0766
_refine_ls_R_factor_gt           0.0653
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1247P)²+0.2651P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1702
_refine_ls_wR_factor_ref         0.1783
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3058
_reflns_number_total             3448
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ob00657c2.cif
_cod_data_source_block           NV2222
_cod_database_code               7159514
_shelx_shelxl_version_number     2018/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.246
_oxdiff_exptl_absorpt_empirical_full_max 2.187
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.82481(6) 0.56643(6) 0.86534(3) 0.0300(2) Uani 1 1 d . . . . .
O1 O 0.2542(2) 0.2822(2) 0.77663(13) 0.0449(4) Uani 1 1 d . . . . .
O2 O 0.6408(2) 0.1912(3) 0.49089(12) 0.0535(5) Uani 1 1 d . . . . .
O3 O 0.9446(2) 0.1926(3) 0.52653(12) 0.0544(5) Uani 1 1 d . . . . .
N1 N 0.3567(2) 0.4597(2) 0.70232(14) 0.0343(4) Uani 1 1 d . . . . .
C1 C 0.8647(2) 0.3738(2) 0.87679(14) 0.0267(4) Uani 1 1 d . . . . .
H11 H 0.974971 0.345910 0.848357 0.032 Uiso 1 1 calc R U . . .
H12 H 0.892261 0.378147 0.948661 0.032 Uiso 1 1 calc R U . . .
C2 C 0.7035(2) 0.2434(2) 0.82496(13) 0.0244(4) Uani 1 1 d . . . . .
H2 H 0.592431 0.279304 0.851089 0.029 Uiso 1 1 calc R U . . .
C3 C 0.6607(2) 0.2209(2) 0.71210(14) 0.0251(4) Uani 1 1 d . . . . .
C4 C 0.4584(3) 0.1980(3) 0.66467(15) 0.0314(4) Uani 1 1 d . . . . .
H41 H 0.403332 0.092070 0.663050 0.038 Uiso 1 1 calc R U . . .
H42 H 0.448116 0.203881 0.594737 0.038 Uiso 1 1 calc R U . . .
C5 C 0.3485(2) 0.3176(3) 0.71908(15) 0.0315(5) Uani 1 1 d . . . . .
C6 C 0.2471(3) 0.5715(3) 0.7530(2) 0.0472(6) Uani 1 1 d . . . . .
H61 H 0.119846 0.549408 0.716447 0.071 Uiso 1 1 calc R U . . .
H62 H 0.298435 0.677659 0.755517 0.071 Uiso 1 1 calc R U . . .
H63 H 0.249522 0.562497 0.821215 0.071 Uiso 1 1 calc R U . . .
C7 C 0.4682(3) 0.5126(3) 0.63761(18) 0.0387(5) Uani 1 1 d . . . . .
H71 H 0.577858 0.581477 0.678570 0.058 Uiso 1 1 calc R U . . .
H72 H 0.396126 0.569714 0.597601 0.058 Uiso 1 1 calc R U . . .
H73 H 0.505643 0.422069 0.593134 0.058 Uiso 1 1 calc R U . . .
C8 C 0.6699(3) 0.6138(3) 0.95142(18) 0.0388(5) Uani 1 1 d . . . . .
H81 H 0.552579 0.545481 0.924936 0.058 Uiso 1 1 calc R U . . .
H82 H 0.648760 0.722940 0.960234 0.058 Uiso 1 1 calc R U . . .
H83 H 0.723840 0.598777 1.016011 0.058 Uiso 1 1 calc R U . . .
C9 C 0.7352(3) 0.0884(2) 0.85597(15) 0.0298(4) Uani 1 1 d . . . . .
C10 C 0.5846(3) -0.0442(3) 0.79551(18) 0.0436(6) Uani 1 1 d . . . . .
H101 H 0.463622 -0.011556 0.802623 0.065 Uiso 1 1 calc R U . . .
H102 H 0.598197 -0.136664 0.820277 0.065 Uiso 1 1 calc R U . . .
H103 H 0.595477 -0.069371 0.724893 0.065 Uiso 1 1 calc R U . . .
C11 C 0.7232(3) 0.1156(3) 0.96675(17) 0.0401(5) Uani 1 1 d . . . . .
H111 H 0.822833 0.196292 1.007452 0.060 Uiso 1 1 calc R U . . .
H112 H 0.734806 0.018165 0.985952 0.060 Uiso 1 1 calc R U . . .
H113 H 0.604348 0.149740 0.977616 0.060 Uiso 1 1 calc R U . . .
C12 C 0.9234(3) 0.0382(3) 0.84122(19) 0.0410(5) Uani 1 1 d . . . . .
H121 H 0.937846 0.030205 0.772140 0.062 Uiso 1 1 calc R U . . .
H122 H 0.931881 -0.063472 0.855028 0.062 Uiso 1 1 calc R U . . .
H123 H 1.020754 0.115900 0.887043 0.062 Uiso 1 1 calc R U . . .
C13 C 0.7970(3) 0.2181(2) 0.66013(14) 0.0296(4) Uani 1 1 d . . . . .
H13 H 0.918531 0.229811 0.696983 0.036 Uiso 1 1 calc R U . . .
C14 C 0.7789(3) 0.1987(3) 0.55161(15) 0.0334(5) Uani 1 1 d . . . . .
C15 C 0.9520(4) 0.1725(4) 0.42137(19) 0.0563(7) Uani 1 1 d . . . . .
H151 H 0.842522 0.207485 0.387664 0.068 Uiso 1 1 calc R U . . .
H152 H 0.954014 0.061091 0.387944 0.068 Uiso 1 1 calc R U . . .
C16 C 1.1205(5) 0.2668(5) 0.4156(2) 0.0689(10) Uani 1 1 d . . . . .
H161 H 1.127851 0.256791 0.345420 0.103 Uiso 1 1 calc R U . . .
H162 H 1.228121 0.229845 0.447955 0.103 Uiso 1 1 calc R U . . .
H163 H 1.117934 0.376620 0.449724 0.103 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 1 -2 0.0138
0 -1 2 0.0218
0 -1 -1 0.0660
0 1 1 0.0673
-1 0 0 0.1052
2 -1 0 0.0590
-1 -4 5 0.0209
-3 -1 7 0.0877
0 6 -4 0.0372
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 S1 C1 100.18(10) . . ?
C14 O3 C15 116.71(19) . . ?
C5 N1 C7 125.16(19) . . ?
C5 N1 C6 118.13(19) . . ?
C7 N1 C6 116.7(2) . . ?
C2 C1 S1 114.93(12) . . ?
C2 C1 H11 108.5 . . ?
S1 C1 H11 108.5 . . ?
C2 C1 H12 108.5 . . ?
S1 C1 H12 108.5 . . ?
H11 C1 H12 107.5 . . ?
C3 C2 C1 111.99(15) . . ?
C3 C2 C9 113.85(15) . . ?
C1 C2 C9 111.08(14) . . ?
C3 C2 H2 106.5 . . ?
C1 C2 H2 106.5 . . ?
C9 C2 H2 106.5 . . ?
C13 C3 C4 123.49(17) . . ?
C13 C3 C2 120.33(16) . . ?
C4 C3 C2 116.15(16) . . ?
C3 C4 C5 113.81(16) . . ?
C3 C4 H41 108.8 . . ?
C5 C4 H41 108.8 . . ?
C3 C4 H42 108.8 . . ?
C5 C4 H42 108.8 . . ?
H41 C4 H42 107.7 . . ?
O1 C5 N1 121.6(2) . . ?
O1 C5 C4 119.6(2) . . ?
N1 C5 C4 118.79(18) . . ?
N1 C6 H61 109.5 . . ?
N1 C6 H62 109.5 . . ?
H61 C6 H62 109.5 . . ?
N1 C6 H63 109.5 . . ?
H61 C6 H63 109.5 . . ?
H62 C6 H63 109.5 . . ?
N1 C7 H71 109.5 . . ?
N1 C7 H72 109.5 . . ?
H71 C7 H72 109.5 . . ?
N1 C7 H73 109.5 . . ?
H71 C7 H73 109.5 . . ?
H72 C7 H73 109.5 . . ?
S1 C8 H81 109.5 . . ?
S1 C8 H82 109.5 . . ?
H81 C8 H82 109.5 . . ?
S1 C8 H83 109.5 . . ?
H81 C8 H83 109.5 . . ?
H82 C8 H83 109.5 . . ?
C10 C9 C12 108.98(19) . . ?
C10 C9 C11 107.91(18) . . ?
C12 C9 C11 108.51(18) . . ?
C10 C9 C2 110.26(16) . . ?
C12 C9 C2 112.45(17) . . ?
C11 C9 C2 108.62(17) . . ?
C9 C10 H101 109.5 . . ?
C9 C10 H102 109.5 . . ?
H101 C10 H102 109.5 . . ?
C9 C10 H103 109.5 . . ?
H101 C10 H103 109.5 . . ?
H102 C10 H103 109.5 . . ?
C9 C11 H111 109.5 . . ?
C9 C11 H112 109.5 . . ?
H111 C11 H112 109.5 . . ?
C9 C11 H113 109.5 . . ?
H111 C11 H113 109.5 . . ?
H112 C11 H113 109.5 . . ?
C9 C12 H121 109.5 . . ?
C9 C12 H122 109.5 . . ?
H121 C12 H122 109.5 . . ?
C9 C12 H123 109.5 . . ?
H121 C12 H123 109.5 . . ?
H122 C12 H123 109.5 . . ?
C3 C13 C14 126.95(17) . . ?
C3 C13 H13 116.5 . . ?
C14 C13 H13 116.5 . . ?
O2 C14 O3 122.26(19) . . ?
O2 C14 C13 128.4(2) . . ?
O3 C14 C13 109.36(17) . . ?
O3 C15 C16 107.8(2) . . ?
O3 C15 H151 110.1 . . ?
C16 C15 H151 110.1 . . ?
O3 C15 H152 110.1 . . ?
C16 C15 H152 110.1 . . ?
H151 C15 H152 108.5 . . ?
C15 C16 H161 109.5 . . ?
C15 C16 H162 109.5 . . ?
H161 C16 H162 109.5 . . ?
C15 C16 H163 109.5 . . ?
H161 C16 H163 109.5 . . ?
H162 C16 H163 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C8 1.798(2) . ?
S1 C1 1.811(2) . ?
O1 C5 1.230(3) . ?
O2 C14 1.212(3) . ?
O3 C14 1.333(3) . ?
O3 C15 1.455(3) . ?
N1 C5 1.345(3) . ?
N1 C7 1.457(3) . ?
N1 C6 1.460(3) . ?
C1 C2 1.542(3) . ?
C1 H11 0.9900 . ?
C1 H12 0.9900 . ?
C2 C3 1.527(2) . ?
C2 C9 1.576(3) . ?
C2 H2 1.0000 . ?
C3 C13 1.337(3) . ?
C3 C4 1.518(2) . ?
C4 C5 1.526(3) . ?
C4 H41 0.9900 . ?
C4 H42 0.9900 . ?
C6 H61 0.9800 . ?
C6 H62 0.9800 . ?
C6 H63 0.9800 . ?
C7 H71 0.9800 . ?
C7 H72 0.9800 . ?
C7 H73 0.9800 . ?
C8 H81 0.9800 . ?
C8 H82 0.9800 . ?
C8 H83 0.9800 . ?
C9 C10 1.529(3) . ?
C9 C12 1.533(3) . ?
C9 C11 1.534(3) . ?
C10 H101 0.9800 . ?
C10 H102 0.9800 . ?
C10 H103 0.9800 . ?
C11 H111 0.9800 . ?
C11 H112 0.9800 . ?
C11 H113 0.9800 . ?
C12 H121 0.9800 . ?
C12 H122 0.9800 . ?
C12 H123 0.9800 . ?
C13 C14 1.476(3) . ?
C13 H13 0.9500 . ?
C15 C16 1.471(4) . ?
C15 H151 0.9900 . ?
C15 H152 0.9900 . ?
C16 H161 0.9800 . ?
C16 H162 0.9800 . ?
C16 H163 0.9800 . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8 S1 C1 C2 74.44(16) . . . . ?
S1 C1 C2 C3 62.35(18) . . . . ?
S1 C1 C2 C9 -169.12(13) . . . . ?
C1 C2 C3 C13 44.4(2) . . . . ?
C9 C2 C3 C13 -82.7(2) . . . . ?
C1 C2 C3 C4 -137.31(17) . . . . ?
C9 C2 C3 C4 95.63(19) . . . . ?
C13 C3 C4 C5 -133.3(2) . . . . ?
C2 C3 C4 C5 48.4(2) . . . . ?
C7 N1 C5 O1 178.31(19) . . . . ?
C6 N1 C5 O1 -1.2(3) . . . . ?
C7 N1 C5 C4 -2.0(3) . . . . ?
C6 N1 C5 C4 178.51(18) . . . . ?
C3 C4 C5 O1 -99.9(2) . . . . ?
C3 C4 C5 N1 80.4(2) . . . . ?
C3 C2 C9 C10 -46.4(2) . . . . ?
C1 C2 C9 C10 -173.97(17) . . . . ?
C3 C2 C9 C12 75.4(2) . . . . ?
C1 C2 C9 C12 -52.1(2) . . . . ?
C3 C2 C9 C11 -164.49(17) . . . . ?
C1 C2 C9 C11 68.0(2) . . . . ?
C4 C3 C13 C14 2.3(3) . . . . ?
C2 C3 C13 C14 -179.50(18) . . . . ?
C15 O3 C14 O2 -1.4(4) . . . . ?
C15 O3 C14 C13 179.6(2) . . . . ?
C3 C13 C14 O2 4.8(4) . . . . ?
C3 C13 C14 O3 -176.3(2) . . . . ?
C14 O3 C15 C16 142.7(3) . . . . ?
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.0010 0.9964 -1.9978 -0.1701 0.1034 -0.1524
-0.0010 -0.9964 1.9978 0.1701 -0.1034 0.1524
0.0012 -1.0069 -0.9927 -0.1338 0.0551 0.1900
-0.0012 1.0069 0.9927 0.1338 -0.0551 -0.1900
-0.9992 -0.0006 -0.0009 0.0636 0.1986 0.0375
1.9989 -1.0022 0.0059 -0.1597 -0.3949 0.1025
-1.0011 -3.9967 5.0000 0.4401 -0.0565 0.6846
-3.0023 -0.9806 6.9795 0.8673 0.2283 0.2021
0.0003 6.0064 -4.0123 -0.2102 0.1977 -1.0145
