Nickel-catalyzed regiodivergent sulfonylarylation of 1,3-enynes to access allenes and dienes.
Chi, Zhuomin; Zhou, Yongchao; Liu, Bingbing; Xu, Xiaojing; Liu, Xueyuan; Liang, Yongmin; Chemical science 15 (2024) 13271–13278; doi:10.1039/d4sc03067b

data_1572156
_publ_section_title
;
 Nickel-catalyzed regiodivergent sulfonylarylation of 1,3-enynes to access
 allenes and dienes.
;
_journal_issue                   33
_journal_name_full               'Chemical science'
_journal_page_first              13271
_journal_page_last               13278
_journal_paper_doi               10.1039/d4sc03067b
_journal_volume                  15
_journal_year                    2024
_chemical_formula_moiety         'C18 H18 O2 S'
_chemical_formula_sum            'C18 H18 O2 S'
_chemical_formula_weight         298.38
_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     dual
_audit_creation_date             2024-03-29
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-03-29 deposited with the CCDC.	2024-07-23 downloaded from the CCDC.
;
_cell_angle_alpha                66.4462(15)
_cell_angle_beta                 78.6780(13)
_cell_angle_gamma                73.4692(12)
_cell_formula_units_Z            2
_cell_length_a                   9.12295(12)
_cell_length_b                   9.29509(14)
_cell_length_c                   10.32066(17)
_cell_measurement_reflns_used    11872
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      76.9700
_cell_measurement_theta_min      4.6630
_cell_volume                     765.70(2)
_computing_cell_refinement       'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_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    113.00 138.00   0.50    0.05    --   64.00  77.00 104.06   50
  2  \w     38.00  64.00   0.50    0.05    --   64.00  77.00 104.06   52
  3  \w     34.00  67.00   0.50    0.05    --   60.00  77.00 -20.60   66
  4  \w     47.00  73.00   0.50    0.05    --   72.00  77.00 -23.20   52
  5  \w     46.00  72.00   0.50    0.05    --   72.00  77.00 -61.34   52
  6  \w     85.00 170.00   0.50    0.05    --  112.00  77.00 -60.00  170
  7  \w     85.00 173.00   0.50    0.05    --  112.00  77.00   0.00  176
  8  \w     85.00 115.00   0.50    0.05    --  112.00  77.00  30.00   60
  9  \w    124.00 150.00   0.50    0.05    --  112.00  77.00 120.00   52
 10  \w     86.00 155.00   0.50    0.05    --  112.00  77.00 150.00  138
 11  \w     86.00 123.00   0.50    0.05    --  112.00  77.00 120.00   74
 12  \w     86.00 151.00   0.50    0.05    --  112.00  77.00  90.00  130
 13  \w    128.00 174.00   0.50    0.05    --  112.00  77.00 -90.00   92
 14  \w     85.00 117.00   0.50    0.05    --  112.00  77.00 -90.00   64
 15  \w     85.00 173.00   0.50    0.05    --  112.00  77.00-150.00  176
 16  \w    149.00 174.00   0.50    0.05    --  112.00  77.00-180.00   50
 17  \w     85.00 125.00   0.50    0.05    --  112.00  77.00-180.00   80
 18  \w     39.00  69.00   0.50    0.05    --   64.00  76.00-149.70   60
 19  \w     85.00 172.00   0.50    0.05    --  112.00  77.00-120.00  174
 20  \w    139.00 164.00   0.50    0.05    --  112.00  77.00  30.00   50
 21  \w    113.00 138.00   0.50    0.05    --   64.00  75.00 158.68   50
 22  \w     39.00  65.00   0.50    0.05    --   64.00  75.00 158.68   52
 23  \w     31.00  69.00   0.50    0.05    --   56.00  76.00  31.98   76
 24  \w     95.00 123.00   0.50    0.05    --  112.00  61.00  90.00   56
 25  \w    127.00 161.00   0.50    0.05    --  112.00  61.00 -30.00   68
 26  \w    112.00 138.00   0.50    0.05    --  112.00  61.00 -60.00   52
 27  \w    145.00 170.00   0.50    0.05    --  112.00  45.00 -60.00   50
 28  \w     94.00 153.00   0.50    0.05    --  112.00  45.00-150.00  118
 29  \w     33.00  69.00   0.50    0.05    --   52.00  75.00 -93.22   72
 30  \w     30.00  68.00   0.50    0.05    --   56.00  75.00-174.76   76
 31  \w    120.00 146.00   0.50    0.05    --  112.00  45.00-180.00   52
 32  \w     95.00 126.00   0.50    0.05    --  112.00  45.00 -60.00   62
 33  \w     93.00 171.00   0.50    0.05    --  112.00  45.00   0.00  156
 34  \w    126.00 175.00   0.50    0.05    --  112.00  45.00  30.00   98
 35  \w     95.00 122.00   0.50    0.05    --  112.00  45.00  90.00   54
 36  \w    127.00 164.00   0.50    0.05    --  112.00  45.00  90.00   74
 37  \w     96.00 166.00   0.50    0.05    --  112.00  45.00  60.00  140
 38  \w     86.00 134.00   0.50    0.05    --  112.00 115.00 166.00   96
 39  \w     80.00 173.00   0.50    0.05    --  112.00 125.00  90.00  186
 40  \w     90.00 115.00   0.50    0.05    --   45.27 169.00 -49.00   50
 41  \w     52.00  83.00   0.50    0.05    --   45.27 169.00 -49.00   62
 42  \w     97.00 123.00   0.50    0.05    --  112.00 169.00 -49.00   52
 43  \w     63.00 119.00   0.50    0.05    --   45.27  77.00  90.00  112
 44  \w     18.00  52.00   0.50    0.05    --   45.27  77.00  90.00   68
 45  \w     28.00  77.00   0.50    0.05    --   45.27  57.00  30.00   98
 46  \w     81.00 107.00   0.50    0.05    --   45.27  57.00  30.00   52
 47  \w     84.00 110.00   0.50    0.05    --   45.27  37.00   0.00   52
 48  \w     28.00  74.00   0.50    0.05    --   45.27  37.00   0.00   92
 49  \w     18.00  44.00   0.50    0.05    --   45.27  77.00 -30.00   52
 50  \w     26.00  68.00   0.50    0.05    --   45.27  57.00-120.00   84
 51  \w     19.00  44.00   0.50    0.05    --   45.27  77.00-180.00   50
 52  \w     40.00  68.00   0.50    0.05    --  112.00 -61.00 -90.00   56
 53  \w     39.00  67.00   0.50    0.05    --  112.00 -61.00-120.00   56
 54  \w     50.00  93.00   0.50    0.05    --  112.00 -77.00-180.00   86
 55  \w     59.00  90.00   0.50    0.05    --  112.00 -77.00 -30.00   62
 56  \w     43.00  68.00   0.50    0.05    --  112.00 -61.00   0.00   50
 57  \w     41.00  67.00   0.50    0.05    --  112.00 -61.00  90.00   52
 58  \w     43.00  98.00   0.50    0.05    --  112.00 -77.00 120.00  110
 59  \w     46.00  84.00   0.50    0.05    --  112.00 -77.00 150.00   76
 60  \w     39.00  65.00   0.50    0.05    --  112.00 -94.00 120.00   52
 61  \w     83.00 110.00   0.50    0.05    --  112.00-125.00  30.00   54
 62  \w     48.00 112.00   0.50    0.05    --  112.00-125.00   0.00  128
 63  \w     42.00  74.00   0.50    0.05    --  112.00-125.00  30.00   64
 64  \w     43.00 112.00   0.50    0.05    --  112.00-125.00 120.00  138
 65  \w     78.00 112.00   0.50    0.05    --  112.00-125.00  60.00   68
 66  \w     42.00  71.00   0.50    0.05    --  112.00-125.00  60.00   58
 67  \w     61.00  87.00   0.50    0.05    --  112.00-115.00  76.00   52
 68  \w     21.00  50.00   0.50    0.05    --   45.27-115.00  76.00   58
 69  \w     71.00  99.00   0.50    0.05    --  112.00 -94.00 120.00   56
 70  \w     56.00  81.00   0.50    0.05    --   45.27-169.00 -67.00   50
 71  \w    105.00 141.00   0.50    0.05    --  112.00-169.00 -67.00   72
 72  \w     42.00  73.00   0.50    0.05    --  112.00-125.00-120.00   62
 73  \w     55.00  81.00   0.50    0.05    --  112.00 -94.00-120.00   52
 74  \w     61.00  86.00   0.50    0.05    --  112.00 -94.00 -90.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0588212000
_diffrn_orient_matrix_UB_12      -0.1549828000
_diffrn_orient_matrix_UB_13      0.0838459000
_diffrn_orient_matrix_UB_21      0.0166392000
_diffrn_orient_matrix_UB_22      -0.0327732000
_diffrn_orient_matrix_UB_23      -0.1377904000
_diffrn_orient_matrix_UB_31      0.1660355000
_diffrn_orient_matrix_UB_32      -0.0970027000
_diffrn_orient_matrix_UB_33      0.0271259000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0281
_diffrn_reflns_av_unetI/netI     0.0175
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            12187
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        66.590
_diffrn_reflns_theta_max         66.590
_diffrn_reflns_theta_min         4.695
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.883
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77624
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.93a (Rigaku Oxford Diffraction, 2023)
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    1.294
_exptl_crystal_description       block
_exptl_crystal_F_000             316
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.318
_refine_diff_density_min         -0.332
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         2674
_refine_ls_number_restraints     61
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0317
_refine_ls_R_factor_gt           0.0313
_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^)+(0.0468P)^2^+0.2822P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0855
_refine_ls_wR_factor_ref         0.0859
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2616
_reflns_number_total             2674
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc03067b2.cif
_cod_data_source_block           chizhm_0104_auto
_cod_depositor_comments          'Adding full bibliography for 1572156.cif.'
_cod_database_code               1572156
_shelx_shelxl_version_number     2016/6
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C2-C10
 1.54 with sigma of 0.02
 C2-C10 \\sim C2A-C10
 with sigma of 0.02
 C10-C17 \\sim C10-C17A
 with sigma of 0.02
3. Rigid bond restraints
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
C2 \\sim C17: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02
within 2A
5. Others
 Sof(C2A)=Sof(H2AA)=Sof(H2AB)=Sof(H2AC)=Sof(C17A)=Sof(H17C)=Sof(H17D)=1-FVAR(1)
 Sof(C2)=Sof(H2A)=Sof(H2B)=Sof(H2C)=Sof(C17)=Sof(H17A)=Sof(H17B)=FVAR(1)
6.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3), C7(H7), C9(H9), C11(H11), C12(H12), C13(H13), C14(H14),
 C16(H16), C18(H18)
6.b X=CH2 refined with riding coordinates:
 C17(H17A,H17B), C17A(H17C,H17D)
6.c Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C15(H15A,H15B,H15C), C2A(H2AA,H2AB,H2AC)
;
_shelx_res_checksum              45253
_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 1.709
_oxdiff_exptl_absorpt_empirical_full_min 0.336