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_4518718
_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 Cl N O2 S2'
_chemical_formula_sum            'C12 H8 Cl N O2 S2'
_chemical_formula_weight         297.76
_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                77.313(7)
_cell_angle_beta                 81.768(8)
_cell_angle_gamma                74.085(9)
_cell_formula_units_Z            2
_cell_length_a                   7.4862(8)
_cell_length_b                   7.6173(7)
_cell_length_c                   12.2600(9)
_cell_measurement_reflns_used    629
_cell_measurement_temperature    299.8(2)
_cell_measurement_theta_max      42.1740
_cell_measurement_theta_min      6.1570
_cell_volume                     653.34(11)
_computing_cell_refinement       'CrysAlisPro 1.171.39.43a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.43a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.43a (Rigaku OD, 2018)'
_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      299.8(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.5357
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.862
_diffrn_measured_fraction_theta_max 0.862
_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    -63.00  33.00   1.00    7.92    --  -41.84  37.00  30.00   96
  2  \w   -110.00 -16.00   1.00    7.92    --  -41.84 -57.00  90.00   94
  3  \w    -63.00  31.00   1.00    7.92    --  -41.84  57.00-120.00   94
  4  \w     34.00  60.00   1.00    7.92    --   41.84-125.00 -60.00   26
  5  \w     46.00  58.00   1.00    7.92    --   41.84-125.00  60.00   12
;
_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      0.1455985000
_diffrn_orient_matrix_UB_12      -0.1880874000
_diffrn_orient_matrix_UB_13      0.0032136000
_diffrn_orient_matrix_UB_21      -0.1568071000
_diffrn_orient_matrix_UB_22      -0.1020220000
_diffrn_orient_matrix_UB_23      0.0338527000
_diffrn_orient_matrix_UB_31      -0.0191118000
_diffrn_orient_matrix_UB_32      0.0095430000
_diffrn_orient_matrix_UB_33      -0.1247571000
_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  0.0038
_diffrn_reflns_av_unetI/netI     0.0112
_diffrn_reflns_Laue_measured_fraction_full 0.862
_diffrn_reflns_Laue_measured_fraction_max 0.862
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            1021
_diffrn_reflns_point_group_measured_fraction_full 0.862
_diffrn_reflns_point_group_measured_fraction_max 0.862
_diffrn_reflns_theta_full        42.707
_diffrn_reflns_theta_max         42.707
_diffrn_reflns_theta_min         7.436
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    5.524
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63733
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.43a (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    1.514
_exptl_crystal_description       block
_exptl_crystal_F_000             304
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.133
_refine_diff_density_min         -0.126
_refine_diff_density_rms         0.031
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     188
_refine_ls_number_reflns         803
_refine_ls_number_restraints     107
_refine_ls_restrained_S_all      1.258
_refine_ls_R_factor_all          0.0433
_refine_ls_R_factor_gt           0.0393
_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^)+(0.0530P)^2^+0.5730P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1005
_refine_ls_wR_factor_ref         0.1035
_reflns_Friedel_coverage         0.000
_reflns_number_gt                711
_reflns_number_total             803
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            sc1c02240_si_001.cif
_cod_data_source_block           4no2-ss_4cl
_cod_depositor_comments
'Adding full bibliography for 4518716--4518724.cif.'
_cod_database_code               4518718
_shelx_shelxl_version_number     2018/1
_chemical_oxdiff_formula         C12H8ClNO2S2
_shelx_estimated_absorpt_t_max   0.809
_shelx_estimated_absorpt_t_min   0.608
_reflns_odcompleteness_completeness 32.81
_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. Restrained distances
 O2'-O1'
 2.1 with sigma of 0.02
 N1'-O2'
 1.2 with sigma of 0.02
 N1'-O1'
 1.2 with sigma of 0.02
 O1'-N1' \\sim O2'-N1' \\sim O1-N1 \\sim O2-N1
 with sigma of 0.02
 N1'-C4' \\sim N1-C4
 with sigma of 0.02
3. Restrained planarity
 O2', N1', C4', O1', C3', C5'
 with sigma of 0.1
4. Rigid bond restraints
 O1', N1', O2'
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C3', C2', C1', C6', C5', C4'
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
5. Uiso/Uaniso restraints and constraints
O1' \\sim N1' \\sim O2': within 2A with sigma of 0.04 and sigma for terminal
atoms of 0.08 within 2A
C3' \\sim C4' \\sim C5' \\sim C6' \\sim C1' \\sim C2': within 2A with sigma of
0.04 and sigma for terminal atoms of 0.08 within 2A
Uanis(O2') \\sim Ueq, Uanis(N1') \\sim Ueq: with sigma of 0.1 and sigma for
terminal atoms of 0.2
Uanis(N1') \\sim Ueq, Uanis(O2') \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(N1') \\sim Ueq: with sigma of 0.008 and sigma for terminal atoms of 0.016
6. Rigid body (RIGU) restrains
 O1, O2, N1, Cl1
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 N1', O1', O2', Cl1'
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 O2', N1', O1'
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 O1', N1', O2'
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
7. Others
 1*[Sof(Cl1')+Sof(O1)+Sof(O2)+Sof(N1)+Sof(Cl1)+Sof(O2')+Sof(O1')+Sof(N1')]=1
 with esd of 0.01
 Sof(Cl1)=Sof(O2')=Sof(O1')=Sof(N1')=1-FVAR(1)
 Sof(Cl1')=Sof(O1)=Sof(O2)=Sof(N1)=FVAR(1)
8.a Aromatic/amide H refined with riding coordinates:
 C3'(H3'), C5'(H5'), C6'(H6'), C2'(H2'), C5(H5), C6(H6), C2(H2), C3(H3)
8.b Fitted hexagon refined as free rotating group:
 C4(C5,C6,C1,C2,C3)
;
_shelx_res_checksum              79362
_shelx_hkl_checksum              22539
_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 1.488
_oxdiff_exptl_absorpt_empirical_full_min 0.770