Permanganate oxidation of α,β-unsaturated carbonyls to vicinal tricarbonyls
Qi, Yue; Yin, Zhixiao; Wen, Xiangxiang; Wang, Chao; Zong, Lili; New Journal of Chemistry 47 (2023) 3249–3254; doi:10.1039/D2NJ05273C

data_7062207
_publ_section_title
;
 Permanganate oxidation of \a,\b-unsaturated carbonyls to vicinal
 tricarbonyls
;
_journal_issue                   7
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              3249
_journal_page_last               3254
_journal_paper_doi               10.1039/D2NJ05273C
_journal_volume                  47
_journal_year                    2023
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C21 H30 N2 O5 S'
_chemical_formula_sum            'C21 H30 N2 O5 S'
_chemical_formula_weight         422.53
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-05-28
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2022-06-24 deposited with the CCDC.	2023-01-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.954(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.8685(5)
_cell_length_b                   7.1800(3)
_cell_length_c                   13.3562(4)
_cell_measurement_reflns_used    2376
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      71.3190
_cell_measurement_theta_min      3.4030
_cell_volume                     1109.19(8)
_computing_cell_refinement       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.968
_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     18.00  58.00   0.50    0.50    --   42.30 -57.00 150.00   80
  2  \w     80.00 105.00   0.50    0.50    --   42.30  77.00-180.00   50
  3  \w    -18.00  73.00   0.50    0.50    --   42.30 -57.00-120.00  182
  4  \w     92.00 131.00   0.50    0.50    --   42.30  77.00  60.00   78
  5  \w     86.00 126.00   0.50    0.50    --   42.30  77.00   0.00   80
  6  \w    -38.00  15.00   0.50    0.50    --   42.30 -57.00 150.00  106
  7  \w     30.00 145.00   0.50    0.50    --  101.60 -82.00 150.00  230
  8  \w     76.00 144.00   0.50    0.50    --  101.60 -82.00-180.00  136
  9  \w     35.00  61.00   0.50    0.50    --  101.60 -82.00-180.00   52
 10  \w     27.00 184.00   0.50    0.50    --  101.60 -12.00  30.00  314
 11  \w     42.00 140.00   0.50    0.50    --  101.60 -38.00 -60.00  196
 12  \w    110.00 138.00   0.50    0.50    --  101.60 -38.00 150.00   56
 13  \w     93.00 119.00   0.50    0.50    --  101.60 -82.00  90.00   52
 14  \w     57.00 101.00   0.50    0.50    --  101.60 -38.00 150.00   88
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1152653000
_diffrn_orient_matrix_UB_12      -0.0208822000
_diffrn_orient_matrix_UB_13      -0.0795429000
_diffrn_orient_matrix_UB_21      -0.0652147000
_diffrn_orient_matrix_UB_22      -0.0082469000
_diffrn_orient_matrix_UB_23      0.0874137000
_diffrn_orient_matrix_UB_31      -0.0139921000
_diffrn_orient_matrix_UB_32      0.2135707000
_diffrn_orient_matrix_UB_33      -0.0045530000
_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  0.0257
_diffrn_reflns_av_unetI/netI     0.0377
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -3
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            4918
_diffrn_reflns_point_group_measured_fraction_full 0.622
_diffrn_reflns_point_group_measured_fraction_max 0.603
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.524
_diffrn_reflns_theta_min         3.395
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.577
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83314
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.33c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.265
_exptl_crystal_description       block
_exptl_crystal_F_000             452
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.241
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.00(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     267
_refine_ls_number_reflns         2610
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0381
_refine_ls_R_factor_gt           0.0340
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0443P)^2^+0.1907P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0868
_refine_ls_wR_factor_ref         0.0892
_reflns_Friedel_coverage         0.148
_reflns_Friedel_fraction_full    0.183
_reflns_Friedel_fraction_max     0.170
_reflns_number_gt                2386
_reflns_number_total             2610
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2nj05273c2.cif
_cod_data_source_block           2351
_cod_depositor_comments          'Adding full bibliography for 7062207.cif.'
_cod_database_code               7062207
_shelx_shelxl_version_number     2017/1
_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:
 C4(H4), C6(H6), C9(H9), C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C7(H7A,H7B), C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C16(H16), C17(H17), C19(H19), C20(H20)
2.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C14(H14A,H14B,
 H14C), C21(H21A,H21B,H21C)
;
_shelx_res_checksum              40407
_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 1.556
_oxdiff_exptl_absorpt_empirical_full_min 0.713