Copper-catalyzed direct decarboxylative hydrosulfonylation of aryl propiolic acids with sulfonylhydrazides leading to vinylsulfones
Li, Siyu; Li, Xiang; Yang, Fan; Wu, Yangjie; Organic Chemistry Frontiers 2 (2015) 1076–; doi:10.1039/C5QO00212E

data_1553170
_publ_section_title
;
 Copper-catalyzed direct decarboxylative hydrosulfonylation of aryl
 propiolic acids with sulfonylhydrazides leading to vinylsulfones
;
_journal_issue                   9
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              1076
_journal_paper_doi               10.1039/C5QO00212E
_journal_volume                  2
_journal_year                    2015
_chemical_formula_moiety         'C15 H14 O3 S'
_chemical_formula_sum            'C15 H14 O3 S'
_chemical_formula_weight         274.32
_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
_atom_sites_solution_primary     direct
_audit_creation_date             2015-04-15
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2015-04-16 deposited with the CCDC.
2015-07-10 downloaded from the CCDC.
;
_cell_angle_alpha                76.750(5)
_cell_angle_beta                 81.107(5)
_cell_angle_gamma                88.437(5)
_cell_formula_units_Z            4
_cell_length_a                   8.5030(6)
_cell_length_b                   10.6762(5)
_cell_length_c                   15.8607(10)
_cell_measurement_reflns_used    3611
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      70.2380
_cell_measurement_theta_min      5.2560
_cell_volume                     1384.60(15)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
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_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      291.15
_diffrn_detector_area_resol_mean 16.2312
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
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;
  1 omega    2.00   27.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -99.0000 -150.0000 25

  2 omega   15.00   42.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -99.0000 -120.0000 27

  3 omega   25.00   68.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000   30.0000 43

  4 omega  -77.00  -52.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  178.0000  -60.0000 25

  5 omega  -18.00   13.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000   30.0000 31

  6 omega    5.00   95.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000  -99.0000   60.0000 90

  7 omega   26.00   72.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   77.0000 -180.0000 46

  8 omega   30.00   79.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000  -77.0000 -120.0000 49

  9 omega   38.00  125.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   57.0000    0.0000 87

 10 omega   20.00   46.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000  -19.0000 -150.0000 26

 11 omega   37.00  118.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   57.0000  120.0000 81

 12 omega   36.00  123.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   57.0000 -120.0000 87

 13 omega   46.00   97.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000  150.0000 51

 14 omega   63.00  115.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000 -150.0000 52

 15 omega   75.00  100.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000  120.0000 25

 16 omega   40.00   69.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000  120.0000 29

 17 omega  100.00  176.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   30.0000 -120.0000 76

 18 omega   58.00  105.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000 -120.0000 47

 19 omega   41.00   92.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000 -150.0000 51

 20 omega   41.00   85.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000 -120.0000 44

 21 omega   55.00   96.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000  -90.0000 41

 22 omega   40.00   74.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000    0.0000 34

 23 omega   62.00  104.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000  -60.0000 42

 24 omega   68.00  108.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000    0.0000 40

 25 omega   96.00  173.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000  -90.0000 77

 26 omega   63.00   89.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000   60.0000 26

 27 omega   91.00  163.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000 -180.0000 72

 28 omega  111.00  177.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   30.0000  150.0000 66

 29 omega   42.00   91.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000  -30.0000 49

 30 omega   57.00  129.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -61.0000   60.0000 72

 31 omega  -77.00  -32.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  178.0000  120.0000 45

 32 omega  -42.00   24.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  100.0000  -61.0000 66

 33 omega   35.00  125.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   57.0000   60.0000 90

 34 omega   26.00  105.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   77.0000  -90.0000 79
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.1474777000
_diffrn_orient_matrix_UB_12      0.0249305000
_diffrn_orient_matrix_UB_13      0.0394836000
_diffrn_orient_matrix_UB_21      -0.1065160000
_diffrn_orient_matrix_UB_22      0.0007276000
_diffrn_orient_matrix_UB_23      0.0877885000
_diffrn_orient_matrix_UB_31      0.0230663000
_diffrn_orient_matrix_UB_32      -0.1461451000
_diffrn_orient_matrix_UB_33      0.0305004000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0186
_diffrn_reflns_av_unetI/netI     0.0255
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9993
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.071
_diffrn_reflns_theta_max         67.071
_diffrn_reflns_theta_min         4.254
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.091
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91859
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.878
_refine_diff_density_min         -0.349
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     345
_refine_ls_number_reflns         4932
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.093
_refine_ls_R_factor_all          0.0743
_refine_ls_R_factor_gt           0.0630
_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^)+(0.0837P)^2^+0.7038P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1737
_refine_ls_wR_factor_ref         0.1857
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3994
_reflns_number_total             4932
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5qo00212e2.cif
_cod_data_source_block           20150470
_cod_database_code               1553170
_chemical_oxdiff_formula         C20H20N4O4S1
_shelx_estimated_absorpt_t_max   0.718
_shelx_estimated_absorpt_t_min   0.656
_reflns_odcompleteness_completeness 99.78
_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. Restrained distances
 C7A-C8A
 1.38 with sigma of 0.02
3. Rigid bond restraints
 S1A, C8A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C8A, C7A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C6A, C7A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
4.a Aromatic/amide H refined with riding coordinates:
 C1A(H1A), C2A(H2A), C3A(H3A), C4A(H4A), C5A(H5A), C7A(H7A), C8A(H8A),
 C10A(H10A), C11A(H11A), C13A(H13A), C14A(H14A), C1(H1), C2(H2), C3(H3), C4(H4),
  C5(H5), C7(H7), C8(H8), C10(H10), C11(H11), C13(H13), C14(H14)
4.b Idealised Me refined as rotating group:
 C15A(H15A,H15B,H15C), C15(H15D,H15E,H15F)
;
_shelx_res_checksum              18332
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'