Catalytic [2,3]-sigmatropic rearrangement of sulfonium ylides derived from azoalkenes: non-carbenoid Doyle-Kirmse reaction.
Yang, Fu-Yuan; Han, Tian-Jiao; Jia, Shi-Kun; Wang, Min-Can; Mei, Guang-Jian; Chemical communications (Cambridge, England) 59 (2023) 3107–3110; doi:10.1039/d3cc00160a

data_7131312
_publ_section_title
;
 Catalytic [2,3]-sigmatropic rearrangement of sulfonium ylides derived
 from azoalkenes: non-carbenoid Doyle-Kirmse reaction.
;
_journal_issue                   21
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              3107
_journal_page_last               3110
_journal_paper_doi               10.1039/d3cc00160a
_journal_volume                  59
_journal_year                    2023
_chemical_formula_moiety         'C23 H26 N2 O4 S'
_chemical_formula_sum            'C23 H26 N2 O4 S'
_chemical_formula_weight         426.52
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2022-09-29
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2023-01-07 deposited with the CCDC.	2023-02-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 108.178(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.8940(8)
_cell_length_b                   13.8863(6)
_cell_length_c                   14.5801(9)
_cell_measurement_reflns_used    2854
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.9350
_cell_measurement_theta_min      4.4920
_cell_volume                     2287.9(2)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w   -102.00 -39.00   1.00    2.30    --  -33.50 -57.00-180.00   63
  2  \w    -94.00 -57.00   1.00    2.30    --  -33.50 178.00-180.00   37
  3  \w   -108.00 -36.00   1.00    2.30    --  -33.50 178.00  60.00   72
  4  \w   -101.00  -8.00   1.00    2.30    --  -33.50 -77.00 -60.00   93
  5  \w    -81.00 -48.00   1.00    2.30    --  -33.50-176.00 116.00   33
  6  \w     58.00 110.00   1.00    2.30    --   36.47 178.00 120.00   52
  7  \w     59.00  85.00   1.00    2.30    --   36.47 178.00 -90.00   26
  8  \w     48.00 103.00   1.00    2.30    --   36.47  77.00  60.00   55
  9  \w     79.00 104.00   1.00    2.30    --   36.47 178.00  30.00   25
 10  \w     79.00 111.00   1.00   15.00    --  108.00-111.00 -90.00   32
 11  \w     46.00 108.00   1.00   15.00    --  108.00 -30.00  60.00   62
 12  \w     44.00  92.00   1.00   15.00    --  108.00 -45.00  30.00   48
 13  \w     84.00 110.00   1.00   15.00    --  108.00 -94.00 -90.00   26
 14  \w     49.00 124.00   1.00   15.00    --  108.00 -61.00 150.00   75
 15  \w     48.00 103.00   1.00   15.00    --  108.00 -94.00 150.00   55
 16  \w     45.00 110.00   1.00   15.00    --  108.00 -94.00  60.00   65
 17  \w     38.00 178.00   1.00   15.00    --  108.00   0.00  90.00  140
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1277773000
_diffrn_orient_matrix_UB_12      0.0315294000
_diffrn_orient_matrix_UB_13      0.0539862000
_diffrn_orient_matrix_UB_21      0.0312413000
_diffrn_orient_matrix_UB_22      -0.0067451000
_diffrn_orient_matrix_UB_23      -0.0946578000
_diffrn_orient_matrix_UB_31      -0.0359448000
_diffrn_orient_matrix_UB_32      0.1061509000
_diffrn_orient_matrix_UB_33      -0.0220034000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0276
_diffrn_reflns_av_unetI/netI     0.0357
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8969
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.079
_diffrn_reflns_theta_max         67.079
_diffrn_reflns_theta_min         3.912
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.506
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88407
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'light colourless'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.238
_exptl_crystal_description       block
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.416
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         4075
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0627
_refine_ls_R_factor_gt           0.0504
_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^)+(0.0844P)^2^+0.2535P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1357
_refine_ls_wR_factor_ref         0.1500
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3258
_reflns_number_total             4075
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc00160a2.cif
_cod_data_source_block           202209176
_cod_depositor_comments          'Adding full bibliography for 7131312.cif.'
_cod_database_code               7131312
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C30H3O3N2S1
_chemical_oxdiff_usercomment     r
_shelx_estimated_absorpt_t_max   0.864
_shelx_estimated_absorpt_t_min   0.784
_reflns_odcompleteness_completeness 99.74
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C14(H14A,H14B), C17(H17A,H17B)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), C2(H2A), C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C19(H19), C20(H20),
 C21(H21), C22(H22), C23(H23)
2.c X=CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C15(H15A,H15B,H15C)
;
_shelx_res_checksum              87862
_shelx_hkl_checksum              87942
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.139
_oxdiff_exptl_absorpt_empirical_full_min 0.858