Sustainable access to sulfonic acids from halides and thiourea dioxide with air
Zhang, Hui; Wang, Ming; Jiang, Xuefeng; Green Chemistry 22 (2020) 8238–8242; doi:10.1039/D0GC03135F

data_7241699
_publ_section_title
;
 Sustainable access to sulfonic acids from halides and thiourea dioxide
 with air
;
_journal_issue                   23
_journal_name_full               'Green Chemistry'
_journal_page_first              8238
_journal_page_last               8242
_journal_paper_doi               10.1039/D0GC03135F
_journal_volume                  22
_journal_year                    2020
_chemical_formula_moiety         'C13 H11 Na O6 S'
_chemical_formula_sum            'C13 H11 Na O6 S'
_chemical_formula_weight         318.27
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2020-06-11
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-07-20 deposited with the CCDC.	2020-10-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.1480(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.24840(10)
_cell_length_b                   11.35970(10)
_cell_length_c                   8.24560(10)
_cell_measurement_reflns_used    19682
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      74.0710
_cell_measurement_theta_min      4.7470
_cell_volume                     1498.14(2)
_computing_cell_refinement       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.959
_diffrn_measured_fraction_theta_max 0.959
_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    -33.00  -6.00   1.00    1.00    --    0.00 -57.00-180.00   27
  2  \w    -48.00  31.00   1.00    1.00    --    0.00 -82.00  30.00   79
  3  \w    -23.00  44.00   1.00    1.00    --    0.00  57.00-180.00   67
  4  \w    -89.00  19.00   1.00    1.00    --    0.00 -38.00 -60.00  108
  5  \w     54.00  88.00   1.00    1.00    --    0.00  77.00  30.00   34
  6  \w    -78.00 -42.00   1.00    1.00    --    0.00 -57.00 120.00   36
  7  \w     60.00  85.00   1.00    1.00    --    0.00  57.00-180.00   25
  8  \w     29.00  89.00   1.00    1.00    --    0.00  19.00-150.00   60
  9  \w     -8.00  23.00   1.00    1.00    --    0.00 -57.00 120.00   31
 10  \w    -88.00 -47.00   1.00    1.00    --    0.00 -57.00-180.00   41
 11  \w     64.00  89.00   1.00    1.00    --    0.00  57.00  60.00   25
 12  \w    -19.00  44.00   1.00    1.00    --    0.00  57.00  60.00   63
 13  \w     -9.00  21.00   1.00    1.00    --    0.00  19.00-150.00   30
 14  \w     65.00  90.00   1.00    1.00    --   95.80  77.00 -90.00   25
 15  \w     63.00  89.00   1.00    1.00    --   95.80  82.00  30.00   26
 16  \w    112.00 181.00   1.00    1.00    --   95.80  81.00  47.68   69
 17  \w    144.00 170.00   1.00    1.00    --   95.80  72.00  -4.85   26
 18  \w     71.00 104.00   1.00    1.00    --   95.80  72.00  -4.85   33
 19  \w     63.00  89.00   1.00    1.00    --   95.80  81.00  47.68   26
 20  \w     65.00  91.00   1.00    1.00    --   95.80  76.00-126.47   26
 21  \w     78.00 161.00   1.00    1.00    --   95.80  45.00   0.00   83
 22  \w     63.00  88.00   1.00    1.00    --   95.80  82.00-120.00   25
 23  \w     59.00 123.00   1.00    1.00    --   95.80 -82.00  90.00   64
 24  \w     24.00 128.00   1.00    1.00    --   95.80 -82.00 -60.00  104
 25  \w     63.00 185.00   1.00    1.00    --   95.80  82.00   0.00  122
 26  \w     65.00  91.00   1.00    1.00    --   95.80  77.00 -30.00   26
 27  \w    131.00 185.00   1.00    1.00    --   95.80  81.00 156.18   54
 28  \w    132.00 185.00   1.00    1.00    --   95.80  82.00  30.00   53
 29  \w    160.00 185.00   1.00    1.00    --   95.80  82.00  90.00   25
 30  \w     20.00 128.00   1.00    1.00    --   95.80 -82.00-150.00  108
 31  \w     63.00  89.00   1.00    1.00    --   95.80  82.00  90.00   26
 32  \w     63.00  95.00   1.00    1.00    --   95.80  81.00 156.18   32
 33  \w     66.00  95.00   1.00    1.00    --   95.80  74.00 121.15   29
 34  \w     65.00  90.00   1.00    1.00    --   95.80  77.00 150.00   25
 35  \w     63.00  96.00   1.00    1.00    --   95.80  82.00  60.00   33
 36  \w     63.00  89.00   1.00    1.00    --   95.80  82.00 -30.00   26
 37  \w    137.00 185.00   1.00    1.00    --   95.80  82.00 -60.00   48
 38  \w    139.00 164.00   1.00    1.00    --   95.80  77.00 150.00   25
 39  \w    100.00 184.00   1.00    1.00    --   95.80  75.00 -73.56   84
 40  \w     65.00  90.00   1.00    1.00    --   95.80  77.00  90.00   25
 41  \w     65.00 120.00   1.00    1.00    --   95.80  77.00 -60.00   55
 42  \w     65.00  91.00   1.00    1.00    --   95.80  77.00   0.00   26
 43  \w     75.00 171.00   1.00    1.00    --   95.80  45.00-150.00   96
 44  \w     75.00 157.00   1.00    1.00    --   95.80  45.00 -60.00   82
 45  \w     63.00  89.00   1.00    1.00    --   95.80  82.00 -60.00   26
 46  \w     71.00  96.00   1.00    1.00    --   95.80  61.00-150.00   25
 47  \w     65.00  91.00   1.00    1.00    --   95.80  77.00-180.00   26
 48  \w     63.00  89.00   1.00    1.00    --   95.80  82.00-150.00   26
 49  \w     30.00  55.00   1.00    1.00    --   95.80 -82.00  30.00   25
 50  \w     89.00 119.00   1.00    1.00    --   95.80 -82.00  30.00   30
 51  \w     71.00  97.00   1.00    1.00    --   95.80  61.00 -30.00   26
 52  \w     67.00 185.00   1.00    1.00    --   95.80  77.00-120.00  118
 53  \w     63.00  88.00   1.00    1.00    --   95.80  82.00 120.00   25
 54  \w     75.00 127.00   1.00    1.00    --   95.80  45.00  90.00   52
 55  \w     75.00 185.00   1.00    1.00    --   95.80  45.00 120.00  110
 56  \w      6.00 125.00   1.00    1.00    --   95.80 -82.00   0.00  119
 57  \w     75.00 107.00   1.00    1.00    --   95.80  45.00-180.00   32
 58  \w     76.00 164.00   1.00    1.00    --   95.80  45.00 150.00   88
 59  \w     66.00  91.00   1.00    1.00    --   95.80  75.00 -73.56   25
 60  \w    131.00 160.00   1.00    1.00    --   95.80  76.00-126.47   29
 61  \w     68.00 183.00   1.00    1.00    --   95.80  70.00-145.35  115
 62  \w     68.00 112.00   1.00    1.00    --   95.80  70.00  31.05   44
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0785670000
_diffrn_orient_matrix_UB_12      -0.0778986000
_diffrn_orient_matrix_UB_13      -0.0393973000
_diffrn_orient_matrix_UB_21      0.0555604000
_diffrn_orient_matrix_UB_22      -0.1106620000
_diffrn_orient_matrix_UB_23      0.0140903000
_diffrn_orient_matrix_UB_31      -0.0035717000
_diffrn_orient_matrix_UB_32      -0.0082230000
_diffrn_orient_matrix_UB_33      0.1852286000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0486
_diffrn_reflns_av_unetI/netI     0.0220
_diffrn_reflns_Laue_measured_fraction_full 0.959
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            31104
_diffrn_reflns_point_group_measured_fraction_full 0.959
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full        67.074
_diffrn_reflns_theta_max         67.074
_diffrn_reflns_theta_min         4.775
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.432
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.38156
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.32a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.411
_exptl_crystal_description       block
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.640
_refine_diff_density_min         -0.642
_refine_diff_density_rms         0.094
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.166
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     302
_refine_ls_number_reflns         2563
_refine_ls_number_restraints     449
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0733
_refine_ls_R_factor_gt           0.0725
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0247P)^2^+8.4172P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1605
_refine_ls_wR_factor_ref         0.1609
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2515
_reflns_number_total             2563
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0gc03135f2.cif
_cod_data_source_block           exp_1196
_cod_depositor_comments          'Adding full bibliography for 7241699.cif.'
_cod_database_code               7241699
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.669
_shelx_estimated_absorpt_t_min   0.428
_reflns_odcompleteness_completeness 99.82
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2. Restrained planarity
 C16, C15, C14, C13, C11, C12
 with sigma of 0.1
3. Rigid bond restraints
 C2, C3, C5, C6
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C15, C16, C11, C12, C13, C14
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
4. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.01 and sigma
for terminal atoms of 0.02
All non-hydrogen atoms have similar U: within 2A with sigma of 0.01 and sigma
for terminal atoms of 0.02
C1 \\sim C2 \\sim C3 \\sim C4 \\sim C5 \\sim C6 \\sim C1' \\sim C7 \\sim C8
\\sim C4': within 2A with sigma of 0.04 and sigma for terminal atoms of 0.08
C11 \\sim C12 \\sim C13 \\sim C14 \\sim C15 \\sim C16 \\sim C17 \\sim C18 \\sim
C19 \\sim C1A \\sim C1B: within 2A with sigma of 0.04 and sigma for terminal
atoms of 0.08
5. Others
 Fixed Sof: C1(0.5) C2(0.5) H2(0.5) C3(0.5) H3A(0.5) C4(0.5) C5(0.5) H5(0.5)
 C6(0.5) H6(0.5) C1'(0.5) C7(0.5) H7(0.5) C8(0.5) H8(0.5) C4'(0.5) C9(0.5)
 H9(0.5) C10(0.5) H10(0.5) C11(0.5) C12(0.5) H12(0.5) C13(0.5) H13(0.5)
 C14(0.5) H14(0.5) C15(0.5) H15(0.5) C16(0.5) H16(0.5) C17(0.5) C18(0.5)
 H18(0.5) C19(0.5) H19(0.5) C1A(0.5) H1A(0.5) C1B(0.5) H1B(0.5) C20(0.5)
 H20(0.5)
6.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3A), C5(H5), C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C12(H12),
 C13(H13), C14(H14), C15(H15), C16(H16), C18(H18), C19(H19), C1A(H1A), C1B(H1B),
  C20(H20)
6.b Tetrahedral OH refined with riding coordinates:
 O3(H3)
;
_shelx_res_checksum              6206
_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 2.229
_oxdiff_exptl_absorpt_empirical_full_min 0.589