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_7157640
_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         'C34 H26 N2 O3 S4'
_chemical_formula_sum            'C34 H26 N2 O3 S4'
_chemical_formula_weight         638.81
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2019-06-13
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-06-13 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                   12.4820(4)
_cell_length_b                   12.8583(5)
_cell_length_c                   19.5132(7)
_cell_measurement_reflns_used    11903
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.0670
_cell_measurement_theta_min      2.0050
_cell_volume                     3131.82(19)
_computing_cell_refinement       'CrysAlisPro 1.171.40.18b (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.18b (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.18b (Rigaku OD, 2018)'
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_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     19.00  44.00   0.50   13.00    --    5.00  28.00-152.00   50
  2  \w    -74.00 -48.00   0.50   13.00    --  -11.50 -28.00  46.00   52
  3  \w     -2.00  55.00   0.50   13.00    --  -11.50  28.00-152.00  114
  4  \w    -46.00  76.00   0.50   13.00    --  -11.50  57.00 -30.00  244
  5  \w    -99.00  -5.00   0.50   13.00    --  -11.50 -37.00-120.00  188
  6  \w    -13.00  74.00   0.50   13.00    --  -11.50  60.00 -90.00  174
  7  \w     -5.00  22.00   0.50   13.00    --  -11.50  60.00   0.00   54
  8  \w   -100.00  22.00   0.50   13.00    --  -11.50 -60.00   0.00  244
;
_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      -0.0127617000
_diffrn_orient_matrix_UB_12      0.0537452000
_diffrn_orient_matrix_UB_13      -0.0009585000
_diffrn_orient_matrix_UB_21      0.0167327000
_diffrn_orient_matrix_UB_22      0.0022964000
_diffrn_orient_matrix_UB_23      -0.0347461000
_diffrn_orient_matrix_UB_31      -0.0527683000
_diffrn_orient_matrix_UB_32      -0.0121931000
_diffrn_orient_matrix_UB_33      -0.0106788000
_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  0.0888
_diffrn_reflns_av_unetI/netI     0.0675
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            50041
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.500
_diffrn_reflns_theta_min         2.087
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_current           55.0
_diffrn_source_power             2.475
_diffrn_source_target            Mo
_diffrn_source_type              'Rigaku FR-E+ SuperBright'
_diffrn_source_voltage           45.0
_exptl_absorpt_coefficient_mu    0.341
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65384
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.18b (Rigaku Oxford Diffraction, 2018)
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    1.355
_exptl_crystal_description       prism
_exptl_crystal_F_000             1328
_exptl_crystal_recrystallization_method
'The material was recrystallised from --- by slow evaporation'
_exptl_crystal_size_max          0.028
_exptl_crystal_size_mid          0.016
_exptl_crystal_size_min          0.012
_refine_diff_density_max         0.453
_refine_diff_density_min         -0.283
_refine_diff_density_rms         0.065
_refine_ls_abs_structure_details
;
 Flack x determined using 2452 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.04(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.113
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     388
_refine_ls_number_reflns         7916
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.113
_refine_ls_R_factor_all          0.0690
_refine_ls_R_factor_gt           0.0555
_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^)+(0.0237P)^2^+1.2693P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0856
_refine_ls_wR_factor_ref         0.0887
_reflns_Friedel_coverage         0.793
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                6913
_reflns_number_total             7916
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ob01428a4.cif
_cod_data_source_block           2019acc0014_r1_100k
_cod_depositor_comments
'Adding full bibliography for 7157638--7157640.cif.'
_cod_database_code               7157640
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         C24H24N2S2O3
_chemical_oxdiff_usercomment     XX
_diffrn_measurement_device_type2 'Rigaku AFC12 (Right)'
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C12(H12), C26(H26)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C27(H27A,H27B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C14(H14), C15(H15), C16(H16),
 C17(H17), C18(H18), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24), C30(H30),
  C31(H31), C32(H32), C33(H33), C34(H34)
;
_shelx_res_checksum              80144
_shelx_hkl_checksum              95490
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a MITIGEN holder with silicon oil'
_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 2.556
_oxdiff_exptl_absorpt_empirical_full_min 0.547