Alkynyl sulfoxides as α-sulfinyl carbene equivalents: Gold-catalysed oxidative cyclopropanation
Barrett, Matthew J.; Khan, Ghulam Fatima; Davies, Paul; Grainger, Richard S.; Chem. Commun.  (2017) –; doi:10.1039/C7CC02244A

data_7120070
_publ_section_title
;
 Alkynyl sulfoxides as \a-sulfinyl carbene equivalents: Gold-catalysed
 oxidative cyclopropanation
;
_journal_name_full               'Chem. Commun.'
_journal_paper_doi               10.1039/C7CC02244A
_journal_year                    2017
_chemical_formula_moiety         'C12 H12 O2 S'
_chemical_formula_sum            'C12 H12 O2 S'
_chemical_formula_weight         220.28
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2017-01-20
_audit_creation_method
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5292)
;
_audit_update_record
;
2017-01-20 deposited with the CCDC.
2017-05-04 downloaded from the CCDC.
;
_cell_angle_alpha                86.275(4)
_cell_angle_beta                 75.966(4)
_cell_angle_gamma                66.086(4)
_cell_formula_units_Z            2
_cell_length_a                   6.2782(3)
_cell_length_b                   7.1917(3)
_cell_length_c                   12.4920(6)
_cell_measurement_reflns_used    6220
_cell_measurement_temperature    100.01(11)
_cell_measurement_theta_max      74.0700
_cell_measurement_theta_min      3.6240
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_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33c (release 11-04-2014 CrysAlis171 .NET)
(compiled Apr 11 2014,15:12:41)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33c (release 11-04-2014 CrysAlis171 .NET)
(compiled Apr 11 2014,15:12:41)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33c (release 11-04-2014 CrysAlis171 .NET)
(compiled Apr 11 2014,15:12:41)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
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_diffrn_ambient_environment      N~2~
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_diffrn_detector                 'CCD plate'
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_diffrn_measurement_details
;
  1 omega  -49.00   -8.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5607   38.0000  -60.0000 41

  2 omega   -1.00   28.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5607   38.0000  -60.0000 29

  3 omega  -50.00  -20.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5607  -57.0000 -150.0000 30

  4 omega   55.00  114.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       42.5607   38.0000    0.0000 59

  5 omega   85.00  121.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   74.0000   19.7464 36

  6 omega   75.00  106.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6257   77.0000  -30.0000 31

  7 omega   88.00  122.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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  8 omega  144.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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  9 omega  122.00  148.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6257   77.0000  150.0000 26

 10 omega  114.00  167.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6257  125.0000  150.0000 53

 11 omega   80.00  111.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6257   61.0000   30.0000 31

 12 omega   79.00  136.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6257   77.0000   60.0000 57

 13 omega   94.00  173.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6257  125.0000  -30.0000 79

 14 omega  136.00  167.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6257   77.0000 -120.0000 31

 15 omega  128.00  154.00   1.0000    1.0000
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 16 omega  104.00  130.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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 17 omega  102.00  146.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       74.0000   76.0000 -155.9971 44

 18 omega   83.00  108.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6257   45.0000 -120.0000 25

 19 omega   80.00  114.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6257   61.0000 -120.0000 34

 20 omega   77.00  170.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6257   77.0000 -180.0000 93

 21 omega   80.00  105.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6257   61.0000  -30.0000 25

 22 omega   83.00  144.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6257   45.0000  -30.0000 61

 23 omega   77.00  130.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6257   77.0000 -120.0000 53

 24 omega   75.00  157.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6257   77.0000  -90.0000 82

 25 omega   75.00  175.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6257   77.0000   30.0000 100

 26 omega   79.00  176.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6257   77.0000  120.0000 97

 27 omega   75.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6257   77.0000  150.0000 29

 28 omega   75.00  136.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6257   77.0000   90.0000 61

 29 omega   48.00   73.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       74.0000   64.0000  -34.1098 25

 30 omega   43.00   73.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       70.0000   57.0000  -69.5322 30

 31 omega   40.00   68.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       70.0000   74.0000  -11.7640 28

 32 omega   35.00   67.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   77.0000   55.7927 32

 33 omega   42.00   75.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       70.0000   77.0000  105.0224 33

 34 omega   39.00   65.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       70.0000   77.0000   83.0020 26

 35 omega   37.00   63.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   74.0000   19.7464 26

 36 omega   36.00   68.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   76.0000  -63.0271 32

 37 omega   27.00   53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   77.0000  -81.7985 26

 38 omega   25.00   53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       42.5607   38.0000    0.0000 28

 39 omega   19.00   45.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       50.0000   82.0000   -7.6667 26

 40 omega   14.00   40.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       46.0000   79.0000  -38.0623 26

 41 omega   15.00   43.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       46.0000   81.0000 -133.9798 28

 42 omega   35.00   61.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   76.0000 -175.6039 26

 43 omega   44.00   77.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       74.0000   71.0000 -177.8734 33

 44 omega   44.00   82.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       74.0000   76.0000 -155.9971 38

 45 omega   17.00   42.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       50.0000   82.0000   76.1936 25

 46 omega   27.00   68.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   77.0000  133.7049 41

 47 omega   21.00   46.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       50.0000   79.0000  159.8160 25

 48 omega   36.00   95.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6257  -45.0000   90.0000 59

 49 omega   80.00  108.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6257  -94.0000  120.0000 28

 50 omega   35.00  108.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6257  -94.0000  -30.0000 73

 51 omega   67.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6257  -94.0000 -120.0000 37

 52 omega   26.00   93.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       42.5607 -125.0000 -180.0000 67

 53 omega   29.00   99.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6257  -94.0000   90.0000 70

 54 omega  -71.00   28.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5607   77.0000  -30.0000 99

 55 omega -113.00  -61.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5607  -57.0000 -150.0000 52
;
_diffrn_measurement_device       'four-circle diffractometer'
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_diffrn_orient_matrix_UB_11      0.2294067000
_diffrn_orient_matrix_UB_12      -0.1862551000
_diffrn_orient_matrix_UB_13      0.0087018000
_diffrn_orient_matrix_UB_21      0.1539499000
_diffrn_orient_matrix_UB_22      0.1100861000
_diffrn_orient_matrix_UB_23      -0.0647556000
_diffrn_orient_matrix_UB_31      -0.0032558000
_diffrn_orient_matrix_UB_32      0.0904345000
_diffrn_orient_matrix_UB_33      0.1091454000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0222
_diffrn_reflns_av_unetI/netI     0.0169
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
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_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7547
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.041
_diffrn_reflns_theta_min         6.739
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.667
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74229
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33c (release 11-04-2014 CrysAlis171 .NET)
(compiled Apr 11 2014,15:12:41)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.463
_exptl_crystal_F_000             232
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_exptl_crystal_size_min          0.0864
_refine_diff_density_max         0.771
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_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.175
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
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_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.175
_refine_ls_R_factor_all          0.0400
_refine_ls_R_factor_gt           0.0391
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_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0190P)^2^+0.9655P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0964
_refine_ls_wR_factor_ref         0.0967
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1829
_reflns_number_total             1882
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7cc02244a2.cif
_cod_data_source_block           10g
_cod_original_cell_volume        499.87(4)
_cod_database_code               7120070
_shelxl_version_number           2014/6
_chemical_oxdiff_formula         'C12 H12 O2 S'
_reflns_odcompleteness_completeness 99.72
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C10(H10), C11(H11), C12(H12)
;
_shelx_res_checksum              37701
_olex2_submission_special_instructions 'No special instructions were received'