Cyclic β-hydroxy-α-nitrosulfone isomers readily interconvert <i>via</i> open-chain aldehyde forms.
Wade, Peter A.; Tandon, Ruchi; Carroll, Patrick J.; Organic & biomolecular chemistry 21 (2023) 5033–5039; doi:10.1039/d3ob00349c

data_7159382
_publ_section_title
;
 Cyclic &#x3b2;-hydroxy-&#x3b1;-nitrosulfone isomers readily interconvert
 <i>via</i> open-chain aldehyde forms.
;
_journal_issue                   24
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5033
_journal_page_last               5039
_journal_paper_doi               10.1039/d3ob00349c
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         'C18 H18 N2 O9 S2'
_chemical_formula_sum            'C18 H18 N2 O9 S2'
_chemical_formula_weight         470.46
_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
_audit_creation_date             2020-09-17
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2023-03-03 deposited with the CCDC.	2023-05-26 downloaded from the CCDC.
;
_cell_angle_alpha                90.026(2)
_cell_angle_beta                 92.030(2)
_cell_angle_gamma                91.303(2)
_cell_formula_units_Z            4
_cell_length_a                   8.2381(2)
_cell_length_b                   9.8787(3)
_cell_length_c                   25.0484(6)
_cell_measurement_reflns_used    19515
_cell_measurement_temperature    100
_cell_measurement_theta_max      74.28
_cell_measurement_theta_min      16.27
_cell_volume                     2036.67(9)
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2019)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100
_diffrn_detector                 'HPC area detector'
_diffrn_detector_area_resol_mean 10.0
_diffrn_detector_type            HyPix-6000HE
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.984
_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    -69.00  23.00   0.50    0.50    --  -48.77  76.00 103.00  184
  2  \w     29.00 121.00   0.50    0.50    --   48.77  76.00 103.00  184
  3  \w     86.00 178.00   0.50    1.00    --  105.75  76.00 103.00  184
  4  \w     98.00 178.00   0.50    1.00    --  105.75  15.00  90.00  160
  5  \w     98.00 178.00   0.50    1.00    --  105.75  30.00 -30.00  160
  6  \w     98.00 178.00   0.50    1.00    --  105.75  30.00 -90.00  160
  7  \w     98.00 178.00   0.50    1.00    --  105.75  30.00   0.00  160
  8  \w     98.00 178.00   0.50    1.00    --  105.75  30.00  90.00  160
  9  \w     99.00 173.00   0.50    1.00    --  105.75  30.00  30.00  148
 10  \w     98.00 146.00   0.50    1.00    --  105.75  30.00-150.00   96
 11  \w     98.00 178.00   0.50    1.00    --  105.75  15.00-180.00  160
 12  \w     34.00  99.00   0.50    1.00    --  105.75 -76.00 -23.00  130
 13  \w     34.00 128.00   0.50    1.00    --  105.75 -80.00  69.24  188
 14  \w     41.00 122.00   0.50    0.50    --   48.77  19.00 120.00  162
 15  \w     41.00  67.00   0.50    1.00    --  105.75 -77.00 150.00   52
 16  \w     34.00 103.00   0.50    1.00    --  105.75 -77.00 120.00  138
 17  \w     34.00 103.00   0.50    1.00    --  105.75 -77.00   0.00  138
 18  \w     34.00 108.00   0.50    1.00    --  105.75 -78.00-138.71  148
 19  \w     39.00  64.00   0.50    1.00    --  105.75 -61.00-180.00   50
 20  \w     34.00  68.00   0.50    1.00    --  105.75 -61.00-120.00   68
 21  \w     34.00 154.00   0.50    1.00    --  105.75   0.00 -90.00  240
 22  \w     34.00  68.00   0.50    1.00    --  105.75 -61.00   0.00   68
 23  \w     34.00  68.00   0.50    1.00    --  105.75 -61.00  60.00   68
 24  \w     34.00 128.00   0.50    1.00    --  105.75 -80.00  35.65  188
 25  \w     34.00 108.00   0.50    1.00    --  105.75 -78.00-122.95  148
 26  \w     34.00 103.00   0.50    1.00    --  105.75 -77.00 -90.00  138
 27  \w     34.00 127.00   0.50    1.00    --  105.75 -79.00 -69.38  186
 28  \w     34.00  68.00   0.50    1.00    --  105.75 -61.00 -90.00   68
 29  \w     34.00 103.00   0.50    1.00    --  105.75 -77.00 -60.00  138
 30  \w     34.00 128.00   0.50    1.00    --  105.75 -80.00  -5.19  188
 31  \w     34.00 108.00   0.50    1.00    --  105.75 -78.00 164.54  148
 32  \w     34.00 103.00   0.50    1.00    --  105.75 -77.00  90.00  138
 33  \w    -24.00  24.00   0.50    0.50    --   48.77 -19.00 -30.00   96
 34  \w    -22.00  69.00   0.50    0.50    --   48.77 -76.00 -23.00  182
 35  \w     34.00 128.00   0.50    1.00    --  105.75 -80.00-163.59  188
 36  \w    -24.00  24.00   0.50    0.50    --   48.77 -19.00  30.00   96
 37  \w   -104.00 -12.00   0.50    1.00    --  -84.25  76.00 103.00  184
 38  \w   -106.00 -12.00   0.50    1.00    --  -84.25  80.00  56.58  188
 39  \w   -106.00 -12.00   0.50    1.00    --  -84.25  80.00 -57.67  188
 40  \w   -106.00 -12.00   0.50    1.00    --  -84.25  80.00-168.01  188
 41  \w   -121.00 -29.00   0.50    0.50    --  -48.77 -76.00 -23.00  184
 42  \w   -121.00 -41.00   0.50    0.50    --  -48.77 -37.00   0.00  160
 43  \w   -156.00 -64.00   0.50    1.00    --  -84.25 -76.00 -23.00  184
;
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB Synergy-S'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0249343000
_diffrn_orient_matrix_UB_12      -0.1186167000
_diffrn_orient_matrix_UB_13      -0.0396127000
_diffrn_orient_matrix_UB_21      0.1408214000
_diffrn_orient_matrix_UB_22      0.0560657000
_diffrn_orient_matrix_UB_23      -0.0329616000
_diffrn_orient_matrix_UB_31      0.1207498000
_diffrn_orient_matrix_UB_32      -0.0843757000
_diffrn_orient_matrix_UB_33      0.0336423000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0600
_diffrn_reflns_av_unetI/netI     0.0135
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            83834
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.197
_diffrn_reflns_theta_min         3.531
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.878
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7970
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SCALE3 ABSPACK'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.534
_exptl_crystal_description       needle
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.443
_refine_diff_density_min         -0.814
_refine_diff_density_rms         0.081
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     562
_refine_ls_number_reflns         15259
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0579
_refine_ls_R_factor_gt           0.0554
_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^)+(0.0815P)^2^+1.8866P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1538
_refine_ls_wR_factor_ref         0.1561
_reflns_number_gt                14264
_reflns_number_total             15259
_reflns_threshold_expression     'I > 2\s(I)'
_twin_special_details
;
Component 2 rotated by 179.9408\% 
around [-0.00 1.00 0.00] (reciprocal) or [0.03 1.00 0.00] (direct)
;
_cod_data_source_file            d3ob00349c3.cif
_cod_data_source_block           99511
_cod_depositor_comments          'Adding full bibliography for 7159382.cif.'
_cod_database_code               7159382
_shelx_shelxl_version_number     2018/3
_shelx_res_checksum              7958
_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 1.615
_oxdiff_exptl_absorpt_empirical_full_min 0.660
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2