Regio- and stereoselective electrochemical synthesis of sulfonylated enethers from alkynes and sulfonyl hydrazides
Du, Wu-Bo; Wang, Ning-Ning; Pan, Chao; Ni, Shao-Fei; Wen, Li-Rong; Li, Ming; Zhang, Lin-Bao; Green Chemistry 23 (2021) 2420–2426; doi:10.1039/D1GC00027F

data_7242329
_publ_section_title
;
 Regio- and stereoselective electrochemical synthesis of sulfonylated
 enethers from alkynes and sulfonyl hydrazides
;
_journal_issue                   6
_journal_name_full               'Green Chemistry'
_journal_page_first              2420
_journal_page_last               2426
_journal_paper_doi               10.1039/D1GC00027F
_journal_volume                  23
_journal_year                    2021
_chemical_formula_moiety         'C17 H18 O3 S'
_chemical_formula_sum            'C17 H18 O3 S'
_chemical_formula_weight         302.37
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-08-12
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-08-19 deposited with the CCDC.	2021-02-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 116.8711(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.40316(12)
_cell_length_b                   7.20606(3)
_cell_length_c                   15.43887(9)
_cell_measurement_reflns_used    20963
_cell_measurement_temperature    170.00(15)
_cell_measurement_theta_max      75.3900
_cell_measurement_theta_min      3.2040
_cell_volume                     1528.62(2)
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_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      170.00(15)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.963
_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   -109.00 -84.00   0.50    0.05    --  -47.20 -38.00-151.00   50
  2  \w    -33.00  20.00   0.50    0.05    --  -47.20  38.00   3.00  106
  3  \w     48.00  78.00   0.50    0.05    --   47.20  38.00   3.00   60
  4  \w      4.00  46.00   0.50    0.05    --   47.20 -38.00-151.00   84
  5  \w   -127.00 -90.00   0.50    0.05    --  -99.00 -38.00-151.00   74
  6  \w     91.00 131.00   0.50    0.05    --  103.25  38.00   3.00   80
  7  \w   -119.00 -74.00   0.50    0.05    --  -47.20-125.00 -90.00   90
  8  \w   -120.00 -75.00   0.50    0.05    --  -47.20-125.00   0.00   90
  9  \w   -113.00 -74.00   0.50    0.05    --  -47.20-125.00 120.00   78
 10  \w     35.00  74.00   0.50    0.05    --   47.20  57.00  90.00   78
 11  \w     58.00  85.00   0.50    0.05    --   47.20  38.00  60.00   54
 12  \w     33.00 116.00   0.50    0.05    --   47.20  57.00 150.00  166
 13  \w    -22.00   8.00   0.50    0.05    --   47.20 -19.00  90.00   60
 14  \w     33.00  68.00   0.50    0.05    --   47.20  57.00 120.00   70
 15  \w   -108.00 -82.00   0.50    0.05    --  -99.00 -61.00 150.00   52
 16  \w   -110.00 -78.00   0.50    0.05    --  -99.00 -73.00-177.11   64
 17  \w   -115.00 -82.00   0.50    0.05    --  -99.00 -62.00  76.53   66
 18  \w   -150.00-124.00   0.50    0.05    --  -99.00 -77.00  90.00   52
 19  \w   -117.00 -86.00   0.50    0.05    --  -99.00 -52.00 101.66   62
 20  \w   -168.00-114.00   0.50    0.05    --  -99.00 -70.00 147.49  108
 21  \w   -105.00 -79.00   0.50    0.05    --  -99.00 -77.00-180.00   52
 22  \w   -153.00-126.00   0.50    0.05    --  -99.00 -66.00 129.05   54
 23  \w    -65.00 -31.00   0.50    0.05    --  -99.00  61.00 150.00   68
 24  \w   -159.00-121.00   0.50    0.05    --  -99.00 -45.00  30.00   76
 25  \w   -146.00 -86.00   0.50    0.05    --  -99.00 -45.00  60.00  120
 26  \w   -125.00 -81.00   0.50    0.05    --  -99.00 -66.00 129.05   88
 27  \w    -68.00 -35.00   0.50    0.05    --  -99.00  61.00  30.00   66
 28  \w   -165.00-121.00   0.50    0.05    --  -99.00 -73.00-177.11   88
 29  \w   -116.00 -85.00   0.50    0.05    --  -99.00 -50.00  88.01   62
 30  \w   -148.00 -82.00   0.50    0.05    --  -99.00 -61.00  90.00  132
 31  \w   -108.00 -82.00   0.50    0.05    --  -99.00 -61.00 120.00   52
 32  \w   -102.00 -76.00   0.50    0.05    --  -99.00 -77.00  90.00   52
 33  \w   -100.00 -75.00   0.50    0.05    --  -99.00 -79.00 115.00   50
 34  \w   -156.00 -82.00   0.50    0.05    --  -99.00 -61.00  60.00  148
 35  \w   -166.00-141.00   0.50    0.05    --  -99.00 -79.00 115.00   50
 36  \w   -106.00 -80.00   0.50    0.05    --  -99.00 -70.00 147.49   52
 37  \w   -166.00-124.00   0.50    0.05    --  -99.00 -30.00 150.00   84
 38  \w   -121.00 -82.00   0.50    0.05    --  -99.00 -62.00 146.15   78
 39  \w   -103.00 -78.00   0.50    0.05    --  -99.00 -73.00 101.26   50
 40  \w   -103.00 -77.00   0.50    0.05    --  -99.00 -77.00 120.00   52
 41  \w   -121.00 -87.00   0.50    0.05    --  -99.00-125.00 -30.00   68
 42  \w   -152.00-127.00   0.50    0.05    --  -99.00 -72.00 143.58   50
 43  \w   -103.00 -78.00   0.50    0.05    --  -99.00 -72.00 143.58   50
 44  \w     81.00 126.00   0.50    0.05    --  103.25 125.00-120.00   90
 45  \w     37.00  74.00   0.50    0.05    --  103.25 -61.00 120.00   74
 46  \w     43.00  74.00   0.50    0.05    --  103.25 -61.00  60.00   62
 47  \w     31.00  75.00   0.50    0.05    --  103.25 -61.00-180.00   88
 48  \w     92.00 161.00   0.50    0.05    --  103.25  45.00  60.00  138
 49  \w     32.00  67.00   0.50    0.05    --  103.25 -61.00-150.00   70
 50  \w     81.00 169.00   0.50    0.05    --  103.25  77.00 150.00  176
 51  \w    127.00 152.00   0.50    0.05    --  103.25  77.00 120.00   50
 52  \w     82.00 109.00   0.50    0.05    --  103.25  77.00 120.00   54
 53  \w     41.00  75.00   0.50    0.05    --  103.25 -61.00   0.00   68
 54  \w     56.00 106.00   0.50    0.05    --  103.25 -94.00-120.00  100
 55  \w     45.00 109.00   0.50    0.05    --  103.25 -77.00  60.00  128
 56  \w     33.00  75.00   0.50    0.05    --  103.25 -61.00-120.00   84
 57  \w     32.00  89.00   0.50    0.05    --  103.25 -94.00 -30.00  114
 58  \w     31.00  69.00   0.50    0.05    --  103.25 -61.00  30.00   76
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0452872000
_diffrn_orient_matrix_UB_12      -0.1945724000
_diffrn_orient_matrix_UB_13      -0.0296377000
_diffrn_orient_matrix_UB_21      -0.0530258000
_diffrn_orient_matrix_UB_22      0.0629201000
_diffrn_orient_matrix_UB_23      -0.1067828000
_diffrn_orient_matrix_UB_31      0.0878012000
_diffrn_orient_matrix_UB_32      -0.0623714000
_diffrn_orient_matrix_UB_33      -0.0152115000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0148
_diffrn_reflns_av_unetI/netI     0.0074
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            23298
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.419
_diffrn_reflns_theta_min         3.364
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.942
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82573
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_description       block
_exptl_crystal_F_000             640
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: petroleum ether / ethyl acetate'
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.326
_refine_diff_density_min         -0.382
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         3042
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0328
_refine_ls_R_factor_gt           0.0326
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0459P)^2^+0.6969P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0873
_refine_ls_wR_factor_ref         0.0874
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3014
_reflns_number_total             3042
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1gc00027f2.cif
_cod_data_source_block           tx2668_pl
_cod_depositor_comments
'Adding full bibliography for 7242329--7242330.cif.'
_cod_database_code               7242329
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         CHOS
_reflns_odcompleteness_completeness 98.16
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_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:
 C2(H2), C3(H3), C5(H5), C6(H6), C13(H13), C14(H14), C15(H15), C16(H16),
 C17(H17)
2.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C9(H9A,H9B,H9C), C11(H11A,H11B,H11C)
;
_shelx_res_checksum              18646
_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 1.264
_oxdiff_exptl_absorpt_empirical_full_min 0.828