General sulfone construction via sulfur dioxide surrogate control
Chen, Shihao; Li, Yaping; Wang, Ming; Jiang, Xuefeng; Green Chemistry 22 (2020) 322–326; doi:10.1039/C9GC03841H

data_7239714
_publ_section_title
;
 General sulfone construction via sulfur dioxide surrogate control
;
_journal_issue                   2
_journal_name_full               'Green Chemistry'
_journal_page_first              322
_journal_page_last               326
_journal_paper_doi               10.1039/C9GC03841H
_journal_volume                  22
_journal_year                    2020
_chemical_formula_moiety         'C11 H10 O2 S'
_chemical_formula_sum            'C11 H10 O2 S'
_chemical_formula_weight         206.25
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-04-23
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-06-08 deposited with the CCDC.	2019-12-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   11.23740(10)
_cell_length_b                   10.35780(10)
_cell_length_c                   16.95870(10)
_cell_measurement_reflns_used    22811
_cell_measurement_temperature    292.7(6)
_cell_measurement_theta_max      74.1800
_cell_measurement_theta_min      4.7960
_cell_volume                     1973.90(3)
_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      air
_diffrn_ambient_temperature      292.7(6)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.993
_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    -19.00  13.00   1.00    1.00    --    0.00  38.00 -60.00   32
  2  \w    -43.00  24.00   1.00    1.00    --    0.00 -77.00 -30.00   67
  3  \w     55.00  81.00   1.00    1.00    --    0.00  57.00-150.00   26
  4  \w    -22.00  42.00   1.00    1.00    --    0.00  57.00  60.00   64
  5  \w    -26.00  19.00   1.00    1.00    --    0.00 -38.00-150.00   45
  6  \w    -23.00  89.00   1.00    1.00    --    0.00  57.00 150.00  112
  7  \w    -82.00 -57.00   1.00    1.00    --    0.00 -77.00 -30.00   25
  8  \w    -87.00 -44.00   1.00    1.00    --    0.00 -38.00-150.00   43
  9  \w     35.00  61.00   1.00    1.00    --    0.00  38.00 -60.00   26
 10  \w     45.00  89.00   1.00    1.00    --    0.00  57.00  60.00   44
 11  \w    -20.00  21.00   1.00    1.00    --    0.00  57.00-150.00   41
 12  \w    -19.00  87.00   1.00    1.00    --    0.00  38.00 -30.00  106
 13  \w    120.00 182.00   1.00    1.00    --   95.80  77.00-128.97   62
 14  \w     65.00  95.00   1.00    1.00    --   95.80  77.00-128.97   30
 15  \w    149.00 175.00   1.00    1.00    --   95.80  64.00 -48.67   26
 16  \w    145.00 182.00   1.00    1.00    --   95.80  63.00 124.08   37
 17  \w     70.00  99.00   1.00    1.00    --   95.80  63.00 124.08   29
 18  \w     70.00 111.00   1.00    1.00    --   95.80  64.00 -48.67   41
 19  \w     69.00 163.00   1.00    1.00    --   95.80  68.00 -34.11   94
 20  \w     43.00 123.00   1.00    1.00    --   95.80 -82.00 150.00   80
 21  \w    135.00 161.00   1.00    1.00    --   95.80  77.00  60.00   26
 22  \w     96.00 183.00   1.00    1.00    --   95.80  82.00  71.29   87
 23  \w     63.00  89.00   1.00    1.00    --   95.80  82.00 120.00   26
 24  \w    105.00 131.00   1.00    1.00    --   95.80  82.00 120.00   26
 25  \w     50.00 128.00   1.00    1.00    --   95.80 -82.00   0.00   78
 26  \w     65.00  90.00   1.00    1.00    --   95.80  77.00   0.00   25
 27  \w    159.00 185.00   1.00    1.00    --   95.80  77.00   0.00   26
 28  \w     71.00 103.00   1.00    1.00    --   95.80  61.00 -60.00   32
 29  \w    109.00 141.00   1.00    1.00    --   95.80  61.00 -60.00   32
 30  \w     65.00  90.00   1.00    1.00    --   95.80  77.00  30.00   25
 31  \w     65.00  91.00   1.00    1.00    --   95.80  77.00  60.00   26
 32  \w     65.00  91.00   1.00    1.00    --   95.80  77.00-180.00   26
 33  \w     63.00  88.00   1.00    1.00    --   95.80  82.00  71.29   25
 34  \w    111.00 180.00   1.00    1.00    --   95.80  57.00   1.93   69
 35  \w     63.00  88.00   1.00    1.00    --   95.80  82.00 -30.00   25
 36  \w     65.00  91.00   1.00    1.00    --   95.80  77.00 -90.00   26
 37  \w     51.00 121.00   1.00    1.00    --   95.80 -82.00  90.00   70
 38  \w     12.00  38.00   1.00    1.00    --   95.80 -82.00  90.00   26
 39  \w     72.00  97.00   1.00    1.00    --   95.80  61.00  60.00   25
 40  \w     63.00  89.00   1.00    1.00    --   95.80  82.00-180.00   26
 41  \w    154.00 185.00   1.00    1.00    --   95.80  82.00-180.00   31
 42  \w     63.00  97.00   1.00    1.00    --   95.80  82.00   0.00   34
 43  \w     66.00  92.00   1.00    1.00    --   95.80  74.00 -30.14   26
 44  \w     75.00 109.00   1.00    1.00    --   95.80  45.00-150.00   34
 45  \w    113.00 156.00   1.00    1.00    --   95.80  45.00-150.00   43
 46  \w     63.00  89.00   1.00    1.00    --   95.80  82.00  30.00   26
 47  \w    157.00 182.00   1.00    1.00    --   95.80  82.00  30.00   25
 48  \w     63.00  89.00   1.00    1.00    --   95.80  82.00  90.00   26
 49  \w     45.00 112.00   1.00    1.00    --   95.80 -82.00-150.00   67
 50  \w     63.00  89.00   1.00    1.00    --   95.80  82.00 150.00   26
 51  \w    104.00 185.00   1.00    1.00    --   95.80  77.00  90.00   81
 52  \w     75.00 181.00   1.00    1.00    --   95.80  45.00  30.00  106
 53  \w     66.00  92.00   1.00    1.00    --   95.80  77.00 120.00   26
 54  \w     69.00 128.00   1.00    1.00    --   95.80 -82.00 -90.00   59
 55  \w     67.00  93.00   1.00    1.00    --   95.80  77.00  90.00   26
 56  \w     65.00  93.00   1.00    1.00    --   95.80  77.00-120.00   28
 57  \w     75.00 152.00   1.00    1.00    --   95.80  45.00  60.00   77
 58  \w     72.00  98.00   1.00    1.00    --   95.80  61.00  90.00   26
 59  \w     64.00  90.00   1.00    1.00    --   95.80  82.00-150.00   26
 60  \w     63.00  88.00   1.00    1.00    --   95.80  82.00 -60.00   25
 61  \w    116.00 185.00   1.00    1.00    --   95.80  82.00 -60.00   69
 62  \w     71.00 105.00   1.00    1.00    --   95.80  61.00 -90.00   34
 63  \w     65.00  90.00   1.00    1.00    --   95.80  77.00-150.00   25
 64  \w     65.00 184.00   1.00    1.00    --   95.80  76.00 144.12  119
 65  \w     70.00 178.00   1.00    1.00    --   95.80  63.00 -80.29  108
 66  \w     72.00  97.00   1.00    1.00    --   95.80  57.00   1.93   25
 67  \w     70.00 185.00   1.00    1.00    --   95.80  64.00-146.77  115
 68  \w     94.00 120.00   1.00    1.00    --   95.80 -82.00 -30.00   26
 69  \w     73.00 175.00   1.00    1.00    --   95.80  53.00-174.12  102
;
_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      0.1152925000
_diffrn_orient_matrix_UB_12      -0.0210151000
_diffrn_orient_matrix_UB_13      -0.0473793000
_diffrn_orient_matrix_UB_21      -0.0725796000
_diffrn_orient_matrix_UB_22      -0.0034372000
_diffrn_orient_matrix_UB_23      -0.0769895000
_diffrn_orient_matrix_UB_31      0.0147690000
_diffrn_orient_matrix_UB_32      0.1473239000
_diffrn_orient_matrix_UB_33      -0.0085826000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0501
_diffrn_reflns_av_unetI/netI     0.0167
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            45068
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.393
_diffrn_reflns_theta_min         5.216
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.664
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.17585
_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    1.388
_exptl_crystal_description       block
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.298
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       0.0023(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     129
_refine_ls_number_reflns         1999
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0351
_refine_ls_R_factor_gt           0.0340
_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^)+(0.0517P)^2^+0.4530P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0916
_refine_ls_wR_factor_ref         0.0927
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1913
_reflns_number_total             1999
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9gc03841h2.cif
_cod_data_source_block           exp_785
_cod_depositor_comments
;Adding full bibliography for 7239713--7239714.cif.

 Adding full bibliography for 7239713--7239714.cif.
;
_cod_database_code               7239714
_shelx_shelxl_version_number     2016/6
_reflns_odcompleteness_completeness 99.90
_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 C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C7(H7), C8(H8), C9(H9), C10(H10)
2.b Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C)
;
_shelx_res_checksum              88271
_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 4.774
_oxdiff_exptl_absorpt_empirical_full_min 0.604