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_4518719
_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         'C13 H11 N O2 S2'
_chemical_formula_sum            'C13 H11 N O2 S2'
_chemical_formula_weight         277.35
_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
_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                 93.577(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.6370(5)
_cell_length_b                   24.4347(18)
_cell_length_c                   7.9539(9)
_cell_measurement_reflns_used    832
_cell_measurement_temperature    299.4(4)
_cell_measurement_theta_max      42.0050
_cell_measurement_theta_min      3.5630
_cell_volume                     1287.4(2)
_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(4)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.5357
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.939
_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    -44.00  -2.00   0.75    6.00    --  -41.91 125.00-180.00   56
  2  \w   -116.00 -20.00   0.75    6.00    --  -41.91 -37.00 -30.00  128
  3  \w    -26.00  11.50   0.75    6.00    --  -41.91  19.00-180.00   50
  4  \w    -41.00  30.25   0.75    6.00    --  -41.91  37.00 120.00   95
  5  \w     17.00  71.75   0.75    6.00    --   41.91-125.00   0.00   73
;
_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      0.0390525000
_diffrn_orient_matrix_UB_12      -0.0431293000
_diffrn_orient_matrix_UB_13      0.1395458000
_diffrn_orient_matrix_UB_21      -0.2293752000
_diffrn_orient_matrix_UB_22      -0.0073156000
_diffrn_orient_matrix_UB_23      0.0112703000
_diffrn_orient_matrix_UB_31      0.0003264000
_diffrn_orient_matrix_UB_32      -0.0453897000
_diffrn_orient_matrix_UB_33      -0.1343067000
_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  0.0237
_diffrn_reflns_av_unetI/netI     0.0363
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.939
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       3
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            1861
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.939
_diffrn_reflns_theta_full        22.500
_diffrn_reflns_theta_max         42.595
_diffrn_reflns_theta_min         3.618
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.696
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78665
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
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    1.431
_exptl_crystal_description       block
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.078
_refine_diff_density_max         0.134
_refine_diff_density_min         -0.127
_refine_diff_density_rms         0.030
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         853
_refine_ls_number_restraints     133
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0538
_refine_ls_R_factor_gt           0.0352
_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^)+(0.0289P)^2^+0.1840P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0663
_refine_ls_wR_factor_ref         0.0749
_reflns_Friedel_coverage         0.000
_reflns_number_gt                668
_reflns_number_total             853
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            sc1c02240_si_001.cif
_cod_data_source_block           4ch3_phssph_2no2
_cod_depositor_comments
'Adding full bibliography for 4518716--4518724.cif.'
_cod_database_code               4518719
_shelx_shelxl_version_number     2018/1
_chemical_oxdiff_formula         'S2C13O2 N'
_shelx_estimated_absorpt_t_max   0.761
_shelx_estimated_absorpt_t_min   0.626
_reflns_odcompleteness_completeness 32.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C6-C5 \\sim C6-C1 \\sim C2-C1 \\sim C3-C2 \\sim C3-C4 \\sim C5-C4
 with sigma of 0.02
 O1-N1 \\sim O2-N1
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.04 and sigma
for terminal atoms of 0.08 within 2A
4. Rigid body (RIGU) restrains
 O2, N1, O1
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5.a Aromatic/amide H refined with riding coordinates:
 C11(H11), C5(H5), C2(H2), C3(H3), C10(H10), C6(H6), C8(H8), C9(H9)
5.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C)
;
_shelx_res_checksum              97123
_shelx_hkl_checksum              29464
_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 1.171
_oxdiff_exptl_absorpt_empirical_full_min 0.780