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_4518716
_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         'C12 H8 Br N O2 S2'
_chemical_formula_sum            'C12 H8 Br N O2 S2'
_chemical_formula_weight         342.22
_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
_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                90.429(13)
_cell_angle_beta                 96.849(14)
_cell_angle_gamma                93.540(14)
_cell_formula_units_Z            2
_cell_length_a                   7.3124(12)
_cell_length_b                   8.0674(14)
_cell_length_c                   11.1844(17)
_cell_measurement_reflns_used    1371
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      64.0850
_cell_measurement_theta_min      3.8850
_cell_volume                     653.76(19)
_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)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.5357
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.786
_diffrn_measured_fraction_theta_max 0.769
_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      3.00  28.00   1.00    6.00    --   40.00  90.00  18.99   25
  2  \w    -80.00  -5.00   1.00    6.00    --  -41.98 125.00  60.00   75
  3  \w    -29.00  27.00   1.00    6.00    --   41.98 -57.00-180.00   56
  4  \w     24.00  83.00   1.00    6.00    --   41.98  37.00-150.00   59
  5  \w     29.00  61.00   1.00    6.00    --   41.98 -57.00-180.00   32
  6  \w      2.00  98.00   1.00    6.00    --   41.98-125.00 -30.00   96
  7  \w      8.00  34.00   1.00    6.00    --   44.00  87.00  62.79   26
  8  \w     71.00 118.00   1.00    6.00    --   48.00  62.00 -95.22   47
  9  \w     16.00  42.00   1.00    6.00    --   48.00  80.00 169.20   26
 10  \w     19.00  54.00   1.00    6.00    --   48.00  62.00 -95.22   35
 11  \w     18.00  43.00   1.00    6.00    --   52.00  82.00  13.77   25
 12  \w     18.00  44.00   1.00    6.00    --   52.00  81.00 111.31   26
 13  \w     19.00  44.00   1.00    6.00    --   52.00  80.00 -72.97   25
 14  \w     19.00  44.00   1.00    6.00    --   52.00  79.00-113.25   25
 15  \w     33.00  67.00   1.00    6.00    --   60.00  76.00-128.11   34
 16  \w     34.00  81.00   1.00    6.00    --   64.00  77.00 -17.13   47
 17  \w     36.00  70.00   1.00    6.00    --   68.00  76.00 -75.28   34
 18  \w    100.00 142.00   1.00    6.00    --   68.00  76.00-177.89   42
 19  \w     36.00  76.00   1.00    6.00    --   68.00  75.00  39.37   40
 20  \w     79.00 106.00   1.00    6.00    --   68.00  76.00 -75.28   27
 21  \w     99.00 131.00   1.00    6.00    --   68.00  77.00 140.90   32
 22  \w     85.00 118.00   1.00    6.00    --   68.00  75.00  71.64   33
 23  \w     40.00  74.00   1.00    6.00    --   68.00  76.00-177.89   34
 24  \w     35.00  80.00   1.00    6.00    --   68.00  77.00 140.90   45
 25  \w     36.00  81.00   1.00    6.00    --   68.00  75.00  71.64   45
 26  \w     53.00  85.00   1.00   14.00    --   84.00  73.00  91.09   32
 27  \w     64.00 112.00   1.00   14.00    --   92.00  68.00 -24.51   48
 28  \w     71.00 110.00   1.00   14.00    --  100.00  68.00  50.92   39
 29  \w    113.00 156.00   1.00   14.00    --  100.00  68.00  50.92   43
 30  \w     80.00 122.00   1.00   14.00    --  112.00  77.00 -90.00   42
 31  \w     42.00 106.00   1.00   14.00    --  112.00-111.00 -60.00   64
 32  \w     84.00 111.00   1.00   14.00    --  112.00  61.00 150.00   27
 33  \w     69.00  97.00   1.00   14.00    --  112.00-111.00-120.00   28
 34  \w     36.00  63.00   1.00   14.00    --  112.00-111.00-120.00   27
 35  \w     38.00 113.00   1.00   14.00    --  112.00-111.00-150.00   75
 36  \w     79.00 122.00   1.00   14.00    --  112.00  77.00-180.00   43
 37  \w     39.00 113.00   1.00   14.00    --  112.00-111.00   0.00   74
 38  \w     79.00 154.00   1.00   14.00    --  112.00  77.00 120.00   75
 39  \w    129.00 157.00   1.00   14.00    --  112.00  77.00  60.00   28
 40  \w     82.00 117.00   1.00   14.00    --  112.00  77.00  60.00   35
 41  \w     84.00 110.00   1.00   14.00    --  112.00  61.00-150.00   26
 42  \w     80.00 120.00   1.00   14.00    --  112.00  77.00-120.00   40
 43  \w     79.00 158.00   1.00   14.00    --  112.00  77.00   0.00   79
 44  \w    116.00 157.00   1.00   14.00    --  112.00  77.00-150.00   41
 45  \w     82.00 107.00   1.00   14.00    --  112.00  77.00-150.00   25
 46  \w    121.00 158.00   1.00   14.00    --  112.00  77.00-120.00   37
 47  \w     92.00 140.00   1.00   14.00    --  112.00  61.00 -60.00   48
 48  \w     40.00  71.00   1.00   14.00    --  112.00 -61.00  60.00   31
 49  \w     84.00 121.00   1.00   14.00    --  112.00  61.00 120.00   37
 50  \w     84.00 154.00   1.00   14.00    --  112.00  77.00 -30.00   70
 51  \w     40.00  71.00   1.00   14.00    --  112.00 -61.00-150.00   31
 52  \w    128.00 156.00   1.00   14.00    --  112.00  77.00-180.00   28
 53  \w    119.00 150.00   1.00   14.00    --  112.00  77.00 150.00   31
 54  \w     81.00 118.00   1.00   14.00    --  112.00  77.00 150.00   37
 55  \w     41.00  68.00   1.00   14.00    --  112.00 -61.00  90.00   27
 56  \w    129.00 154.00   1.00   14.00    --  112.00  61.00  30.00   25
 57  \w     83.00 110.00   1.00   14.00    --  112.00  61.00  30.00   27
 58  \w     91.00 118.00   1.00   14.00    --  112.00  61.00 -90.00   27
 59  \w     40.00  65.00   1.00   14.00    --  112.00 -61.00 -30.00   25
 60  \w     33.00  80.00   1.00   14.00    --  112.00 -94.00  30.00   47
 61  \w     40.00 113.00   1.00   14.00    --  112.00-111.00  90.00   73
 62  \w     85.00 113.00   1.00   14.00    --  112.00  61.00-180.00   28
 63  \w     83.00 111.00   1.00   14.00    --  112.00  61.00-120.00   28
 64  \w     59.00 141.00   1.00   14.00    --  112.00 179.00-120.00   82
 65  \w     79.00 113.00   1.00   14.00    --  112.00  77.00  90.00   34
 66  \w    125.00 154.00   1.00   14.00    --  112.00  77.00 -90.00   29
 67  \w     59.00  99.00   1.00   14.00    --  112.00 179.00  30.00   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      -0.0435216000
_diffrn_orient_matrix_UB_12      0.1397149000
_diffrn_orient_matrix_UB_13      0.0848822000
_diffrn_orient_matrix_UB_21      0.1484411000
_diffrn_orient_matrix_UB_22      0.1165224000
_diffrn_orient_matrix_UB_23      -0.0481794000
_diffrn_orient_matrix_UB_31      -0.1458658000
_diffrn_orient_matrix_UB_32      0.0592989000
_diffrn_orient_matrix_UB_33      -0.0986141000
_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  0.0991
_diffrn_reflns_av_unetI/netI     0.1084
_diffrn_reflns_Laue_measured_fraction_full 0.786
_diffrn_reflns_Laue_measured_fraction_max 0.769
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4766
_diffrn_reflns_point_group_measured_fraction_full 0.786
_diffrn_reflns_point_group_measured_fraction_max 0.769
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.994
_diffrn_reflns_theta_min         3.981
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    7.221
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.001
_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            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.738
_exptl_crystal_description       block
_exptl_crystal_F_000             340
_exptl_crystal_size_max          0.077
_exptl_crystal_size_mid          0.046
_exptl_crystal_size_min          0.028
_refine_diff_density_max         0.426
_refine_diff_density_min         -0.455
_refine_diff_density_rms         0.098
_refine_ls_extinction_coef       0.011(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/1 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         1903
_refine_ls_number_restraints     121
_refine_ls_restrained_S_all      0.987
_refine_ls_R_factor_all          0.1533
_refine_ls_R_factor_gt           0.0859
_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^)+(0.1364P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2208
_refine_ls_wR_factor_ref         0.2932
_reflns_Friedel_coverage         0.000
_reflns_number_gt                907
_reflns_number_total             1903
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            sc1c02240_si_001.cif
_cod_data_source_block           2no2-ss-4br
_cod_depositor_comments
'Adding full bibliography for 4518716--4518724.cif.'
_cod_database_code               4518716
_shelx_shelxl_version_number     2018/1
_chemical_oxdiff_formula         C12BrS2NO2
_shelx_estimated_absorpt_t_max   0.823
_shelx_estimated_absorpt_t_min   0.606
_reflns_odcompleteness_completeness 77.85
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     69.95
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Rigid body (RIGU) restrains
 C7, Br1, C1, C6, C2, C5, C3, C4, S1, S2, C12, C8, C11, C9, N1, C10, O2, O1
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C3(H3), C9(H9), C2(H2), C5(H5), C12(H12), C10(H10), C11(H11)
;
_shelx_res_checksum              51234
_shelx_hkl_checksum              98544
_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
- B-factor correction
;
_oxdiff_exptl_absorpt_empirical_full_max 2.213
_oxdiff_exptl_absorpt_empirical_full_min 0.459