Synthetic and computational investigation of neighboring group participation by a nucleophilic disulfide bond.
Yamamoto, Takuhei; Fukuta, Koki; Kariya, Yuki; Matsuura, Taiki; Hagiwara, Hiroaki; Uno, Bunji; Esaka, Yukihiro; Organic & biomolecular chemistry 21 (2022) 65–68; doi:10.1039/d2ob01574a

data_7159007
_publ_section_title
;
 Synthetic and computational investigation of neighboring group
 participation by a nucleophilic disulfide bond.
;
_journal_issue                   1
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              65
_journal_page_last               68
_journal_paper_doi               10.1039/d2ob01574a
_journal_volume                  21
_journal_year                    2022
_chemical_formula_moiety         'C8 H11 N O S'
_chemical_formula_sum            'C8 H11 N O S'
_chemical_formula_weight         169.24
_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     dual
_audit_creation_date             2022-08-02
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2022-08-03 deposited with the CCDC.	2022-11-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.536(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.0019(4)
_cell_length_b                   7.9707(3)
_cell_length_c                   11.5272(5)
_cell_measurement_reflns_used    6183
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.3770
_cell_measurement_theta_min      2.5480
_cell_volume                     792.89(6)
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrystalClear-SM Expert 2.0 r16 (Rigaku, 2014)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 14.7059
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.832
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \f    -80.00 100.00   0.50   10.00   0.00  10.00   0.00    --   360
  2  \w    -29.50  19.50   0.50   10.00    --   10.00  90.00   0.00   98
  3  \w    -29.50  19.50   0.50   10.00    --   10.00  90.00  90.00   98
  4  \w    -29.50  19.50   0.50   10.00    --   10.00  90.00 180.00   98
;
_diffrn_measurement_device_type  'Rigaku/MSC Mercury CCD'
_diffrn_measurement_method       dtprofit.ref
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0014889000
_diffrn_orient_matrix_UB_12      0.0780580000
_diffrn_orient_matrix_UB_13      -0.0298625000
_diffrn_orient_matrix_UB_21      -0.0066345000
_diffrn_orient_matrix_UB_22      -0.0426795000
_diffrn_orient_matrix_UB_23      -0.0552102000
_diffrn_orient_matrix_UB_31      -0.0819441000
_diffrn_orient_matrix_UB_32      0.0020203000
_diffrn_orient_matrix_UB_33      -0.0133281000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0112
_diffrn_reflns_av_unetI/netI     0.0095
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.832
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7728
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.832
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.314
_diffrn_reflns_theta_min         2.360
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.345
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94410
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.418
_exptl_crystal_description       block
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.915
_refine_diff_density_min         -0.286
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     110
_refine_ls_number_reflns         1975
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0420
_refine_ls_R_factor_gt           0.0409
_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^)+(0.0384P)^2^+1.1594P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0964
_refine_ls_wR_factor_ref         0.0971
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1900
_reflns_number_total             1975
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob01574a2.cif
_cod_data_source_block           TY081_100K
_cod_depositor_comments          'Adding full bibliography for 7159007.cif.'
_cod_database_code               7159007
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C8H11NOS
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2. Others
 Sof(H8B)=Sof(S1A)=1-FVAR(1)
 Sof(H8A)=Sof(S1)=FVAR(1)
3.a Ternary CH refined with riding coordinates:
 C2(H2), C4(H4), C6(H6), C8(H8A), C8(H8B)
3.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C5(H5A,H5B), C7(H7A,H7B)
3.c Aromatic/amide H refined with riding coordinates:
 N1(H1)
;
_shelx_res_checksum              82300
_olex2_exptl_crystal_mounting_method Fiber
_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 1.198
_oxdiff_exptl_absorpt_empirical_full_min 0.873