A fully diastereoselective oxidation of a mesoionic dipole with triplet molecular oxygen.
García de la Concepción, Juan; Ávalos, Martín; Jiménez, José L; Cintas, Pedro; Light, Mark E.; Organic & biomolecular chemistry 18 (2020) 6328–6339; doi:10.1039/d0ob01428a

data_7157638
_publ_section_title
;
 A fully diastereoselective oxidation of a mesoionic dipole with triplet
 molecular oxygen.
;
_journal_issue                   32
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6328
_journal_page_last               6339
_journal_paper_doi               10.1039/d0ob01428a
_journal_volume                  18
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C28 H30 N2 O3 S4'
_chemical_formula_sum            'C28 H30 N2 O3 S4'
_chemical_formula_weight         570.78
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2016-01-07
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2015.11.10 svn.r3248 for OlexSys, GUI svn.r5133)
;
_audit_update_record
;
2018-10-04 deposited with the CCDC.	2020-07-31 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.4421(2)
_cell_length_b                   14.8451(4)
_cell_length_c                   19.2118(4)
_cell_measurement_reflns_used    14506
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.6460
_cell_measurement_theta_min      2.4870
_cell_volume                     2692.90(11)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrystalClear-SM Expert 3.1 b27 (Rigaku, 2013)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku HG Saturn724+ (2x2 bin mode)'
_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    -80.00  20.00   1.00   10.00    --  -19.00 -72.00 150.00  100
  2  \w   -109.00 -34.00   1.00   10.00    --  -19.00 -54.00  90.00   75
  3  \w    -62.00 -42.00   1.00   10.00    --  -19.00 -18.00-180.00   20
  4  \w   -109.00  17.00   1.00   10.00    --  -19.00 -54.00   0.00  126
  5  \w    -76.00   0.00   1.00   10.00    --  -19.00 -72.00-120.00   76
;
_diffrn_measurement_device       'four-circle \k diffractometer'
_diffrn_measurement_device_type  'Rigaku AFC12 FRE-VHF'
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMesh'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0017950000
_diffrn_orient_matrix_UB_12      -0.0431432000
_diffrn_orient_matrix_UB_13      -0.0159167000
_diffrn_orient_matrix_UB_21      0.0046933000
_diffrn_orient_matrix_UB_22      0.0205338000
_diffrn_orient_matrix_UB_23      -0.0332313000
_diffrn_orient_matrix_UB_31      0.0749254000
_diffrn_orient_matrix_UB_32      -0.0003414000
_diffrn_orient_matrix_UB_33      0.0025109000
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  'Confocal mirrors, VHF Varimax'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0688
_diffrn_reflns_av_unetI/netI     0.0430
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            23556
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         28.698
_diffrn_reflns_theta_min         2.942
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           55.0
_diffrn_source_power             2.475
_diffrn_source_target            Mo
_diffrn_source_type              'Rotating Anode'
_diffrn_source_voltage           45.0
_exptl_absorpt_coefficient_mu    0.387
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.34005
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.'
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_description       prism
_exptl_crystal_F_000             1200
_exptl_crystal_recrystallization_method
'The material was recrystallised from --- by slow evaporation'
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.432
_refine_diff_density_min         -0.454
_refine_diff_density_rms         0.064
_refine_ls_abs_structure_details
;
 Flack x determined using 2668 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     338
_refine_ls_number_reflns         6950
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0433
_refine_ls_R_factor_gt           0.0401
_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^)+(0.0701P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0987
_refine_ls_wR_factor_ref         0.1003
_reflns_Friedel_coverage         0.786
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                6514
_reflns_number_total             6950
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ob01428a3.cif
_cod_data_source_block           2016acc0002_r_100k
_cod_depositor_comments
'Adding full bibliography for 7157638--7157640.cif.'
_cod_original_cell_volume        2692.89(11)
_cod_database_code               7157638
_diffrn_measurement_device_type2 'Rigaku AFC12 (Right)'
_reflns_odcompleteness_completeness 95.44
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.55
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2), C4(H4), C25(H25), C26(H26)
2.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C24(H24A,H24B)
2.c Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C13(H13), C14(H14), C15(H15), C17(H17), C18(H18),
 C19(H19), C20(H20), C21(H21)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C3(H3A,H3B,H3C), C27(H27A,H27B,H27C), C28(H28A,H28B,H28C)
;
_shelx_res_checksum              28176
_shelx_hkl_checksum              46214
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_submission    2016-01-04
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a MITIGEN holder in perfluoroether oil'
_olex2_submission_original_sample_id 'DIMQ RX'
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.793
_oxdiff_exptl_absorpt_empirical_full_min 0.341