Squeezing Out the Catalysts: A Sustainable Approach to Disulfide Bond Exchange in Aryl Disulfides
Sobczak, Szymon; Ratajczyk, Paulina; Katrusiak, Andrzej; ACS Sustainable Chemistry & Engineering 9 (2021) 7171–7178; doi:10.1021/acssuschemeng.1c02240

data_4518722
_publ_section_title
;
 Squeezing Out the Catalysts: A Sustainable Approach to Disulfide Bond
 Exchange in Aryl Disulfides
;
_journal_issue                   20
_journal_name_full               'ACS Sustainable Chemistry &amp; Engineering'
_journal_page_first              7171
_journal_page_last               7178
_journal_paper_doi               10.1021/acssuschemeng.1c02240
_journal_volume                  9
_journal_year                    2021
_chemical_formula_moiety         'C14 H14 O2 S2'
_chemical_formula_sum            'C14 H14 O2 S2'
_chemical_formula_weight         278.37
_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   difmap
_audit_creation_date             2020-09-22
_audit_creation_method
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_audit_update_record
;
2020-09-23 deposited with the CCDC.	2020-09-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.9037(2)
_cell_length_b                   12.9800(4)
_cell_length_c                   17.9041(6)
_cell_measurement_reflns_used    7558
_cell_measurement_temperature    299.4(3)
_cell_measurement_theta_max      75.8310
_cell_measurement_theta_min      2.4530
_cell_volume                     1371.99(8)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      299.4(3)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.5357
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.778
_diffrn_measured_fraction_theta_max 0.751
_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      6.00  34.00   1.00    6.50    --   40.00  85.00 114.25   28
  2  \w    -97.00  -2.00   1.00    6.50    --  -41.91 125.00   0.00   95
  3  \w     18.00  87.00   1.00    6.50    --   41.91  37.00 -60.00   69
  4  \w    -37.00  24.00   1.00    6.50    --   41.91 -19.00  90.00   61
  5  \w     79.00 105.00   1.00    6.50    --   41.91  37.00-180.00   26
  6  \w     36.00  64.00   1.00    6.50    --   41.91  37.00-180.00   28
  7  \w     20.00  79.00   1.00    6.50    --   41.91  37.00  60.00   59
  8  \w     -8.00  81.00   1.00    6.50    --   41.91 -99.00-150.00   89
  9  \w    -32.00  40.00   1.00    6.50    --   41.91 -37.00-120.00   72
 10  \w     15.00  40.00   1.00    6.50    --   48.00  80.00  18.99   25
 11  \w     14.00  40.00   1.00    6.50    --   48.00  83.00-110.02   26
 12  \w     18.00  43.00   1.00    6.50    --   52.00  81.00  81.65   25
 13  \w     19.00  44.00   1.00    6.50    --   52.00  80.00 -47.73   25
 14  \w     18.00  43.00   1.00    6.50    --   52.00  82.00 171.23   25
 15  \w     28.00  54.00   1.00    6.50    --   60.00  75.00-162.18   26
 16  \w     32.00  57.00   1.00    6.50    --   64.00  77.00  16.29   25
 17  \w    105.00 143.00   1.00    6.50    --   68.00  75.00 103.51   38
 18  \w     37.00  65.00   1.00    6.50    --   68.00  76.00 -47.28   28
 19  \w     37.00  76.00   1.00    6.50    --   68.00  75.00 103.51   39
 20  \w     36.00  62.00   1.00    6.50    --   68.00  76.00 -21.41   26
 21  \w     40.00  75.00   1.00    6.50    --   72.00  76.00-110.88   35
 22  \w     44.00  72.00   1.00    6.50    --   76.00  76.00-153.49   28
 23  \w     44.00 105.00   1.00    6.50    --   76.00  76.00  33.95   61
 24  \w    120.00 148.00   1.00    6.50    --   76.00  47.00 154.70   28
 25  \w     52.00  87.00   1.00    6.50    --   76.00  47.00 154.70   35
 26  \w     83.00 111.00   1.00   12.00    --  111.24  61.00  90.00   28
 27  \w     82.00 108.00   1.00   12.00    --  111.24  61.00-150.00   26
 28  \w     85.00 113.00   1.00   12.00    --  111.24  61.00  30.00   28
 29  \w    125.00 157.00   1.00   12.00    --  111.24 111.00  60.00   32
 30  \w     37.00 111.00   1.00   12.00    --  111.24-111.00 -60.00   74
 31  \w     36.00 113.00   1.00   12.00    --  111.24-111.00  90.00   77
 32  \w     39.00  71.00   1.00   12.00    --  111.24 -61.00-150.00   32
 33  \w     80.00 158.00   1.00   12.00    --  111.24  77.00 -30.00   78
 34  \w     36.00 110.00   1.00   12.00    --  111.24-111.00  30.00   74
 35  \w     36.00 108.00   1.00   12.00    --  111.24 -94.00 120.00   72
 36  \w     79.00 146.00   1.00   12.00    --  111.24  77.00-120.00   67
 37  \w    115.00 158.00   1.00   12.00    --  111.24  77.00-150.00   43
 38  \w     79.00 104.00   1.00   12.00    --  111.24  77.00-150.00   25
 39  \w     29.00  80.00   1.00   12.00    --  111.24 -94.00-180.00   51
 40  \w     30.00  86.00   1.00   12.00    --  111.24 -94.00 -30.00   56
 41  \w    133.00 158.00   1.00   12.00    --  111.24  77.00 -90.00   25
 42  \w     40.00 107.00   1.00   12.00    --  111.24-111.00-120.00   67
 43  \w    133.00 158.00   1.00   12.00    --  111.24  61.00 120.00   25
 44  \w     80.00 107.00   1.00   12.00    --  111.24  77.00 -90.00   27
 45  \w     86.00 115.00   1.00   12.00    --  111.24  61.00 120.00   29
 46  \w     83.00 115.00   1.00   12.00    --  111.24  61.00 -60.00   32
 47  \w     39.00  71.00   1.00   12.00    --  111.24 -61.00   0.00   32
 48  \w     79.00 156.00   1.00   12.00    --  111.24  77.00  30.00   77
 49  \w     85.00 112.00   1.00   12.00    --  111.24  61.00 150.00   27
 50  \w     83.00 158.00   1.00   12.00    --  111.24  77.00 150.00   75
 51  \w     79.00 157.00   1.00   12.00    --  111.24  77.00 120.00   78
 52  \w     83.00 136.00   1.00   12.00    --  111.24  61.00 -30.00   53
 53  \w     83.00 108.00   1.00   12.00    --  111.24  61.00   0.00   25
 54  \w     39.00  64.00   1.00   12.00    --  111.24 -61.00  60.00   25
 55  \w     82.00 157.00   1.00   12.00    --  111.24  64.00-170.00   75
 56  \w     85.00 110.00   1.00   12.00    --  111.24  61.00-120.00   25
 57  \w    118.00 157.00   1.00   12.00    --  111.24  61.00 -90.00   39
 58  \w     83.00 110.00   1.00   12.00    --  111.24  61.00 -90.00   27
 59  \w    117.00 144.00   1.00   12.00    --  111.24  77.00 -60.00   27
 60  \w     39.00  64.00   1.00   12.00    --  111.24 -61.00 120.00   25
 61  \w    115.00 157.00   1.00   12.00    --  111.24  77.00   0.00   42
 62  \w     80.00 114.00   1.00   12.00    --  111.24  77.00 -60.00   34
 63  \w     80.00 109.00   1.00   12.00    --  111.24  77.00   0.00   29
 64  \w     85.00 152.00   1.00   12.00    --  111.24  61.00  60.00   67
 65  \w    116.00 156.00   1.00   12.00    --  111.24  61.00  90.00   40
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0954978000
_diffrn_orient_matrix_UB_12      -0.0330331000
_diffrn_orient_matrix_UB_13      0.0764003000
_diffrn_orient_matrix_UB_21      -0.0222524000
_diffrn_orient_matrix_UB_22      0.1116239000
_diffrn_orient_matrix_UB_23      0.0283621000
_diffrn_orient_matrix_UB_31      -0.2417265000
_diffrn_orient_matrix_UB_32      -0.0233115000
_diffrn_orient_matrix_UB_33      0.0276297000
_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  0.0295
_diffrn_reflns_av_unetI/netI     0.0205
_diffrn_reflns_Laue_measured_fraction_full 0.778
_diffrn_reflns_Laue_measured_fraction_max 0.751
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            6081
_diffrn_reflns_point_group_measured_fraction_full 0.776
_diffrn_reflns_point_group_measured_fraction_max 0.749
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.579
_diffrn_reflns_theta_min         4.207
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.445
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.735
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'dull colourless'
_exptl_crystal_colour_lustre     dull
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_description       block
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.111
_exptl_crystal_size_min          0.043
_refine_diff_density_max         0.114
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.30(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         1807
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0292
_refine_ls_R_factor_gt           0.0281
_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^)+(0.0525P)^2^+0.0506P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0744
_refine_ls_wR_factor_ref         0.0757
_reflns_Friedel_coverage         0.693
_reflns_Friedel_fraction_full    0.774
_reflns_Friedel_fraction_max     0.745
_reflns_number_gt                1752
_reflns_number_total             1807
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            sc1c02240_si_001.cif
_cod_data_source_block           h3co_phssph_och3
_cod_depositor_comments
'Adding full bibliography for 4518716--4518724.cif.'
_cod_database_code               4518722
_shelx_shelxl_version_number     2018/1
_chemical_oxdiff_formula         S2C14O2H14
_shelx_estimated_absorpt_t_max   0.866
_shelx_estimated_absorpt_t_min   0.480
_reflns_odcompleteness_completeness 75.11
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     69.95
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.70(3)
 0.30(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
;
_shelx_res_checksum              81907
_shelx_hkl_checksum              96604
_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 1.998
_oxdiff_exptl_absorpt_empirical_full_min 0.530