Transition metal-free [2,3]-sigmatropic rearrangement in the reaction of sulfur ylides with allenoates.
García-Castro, Miguel; Moya-Utrera, Federico; Sarabia, Francisco; Organic & biomolecular chemistry 21 (2023) 6096–6102; doi:10.1039/d3ob00657c

data_7159514
_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 &amp; 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 \k-geometry diffractometer'
_diffrn_measurement_device_type
'Oxford Diffraction SuperNova, dual radiation diffractometer'
_diffrn_measurement_method       '\w 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/[\s^2^(Fo^2^)+(0.1247P)^2^+0.2651P] where P=(Fo^2^+2Fc^2^)/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 > 2\s(I)'
_cod_data_source_file            d3ob00657c2.cif
_cod_data_source_block           NV2222
_cod_database_code               7159514
_shelx_shelxl_version_number     2018/3
_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
;
_shelx_res_checksum              19673