Divergent upgrading pathways of sulfones with primary alcohols: nickel-catalyzed α-alkylation under N<sub>2</sub> and metal-free promoted β-olefination in open air.
Yu, Haiping; Fu, Kaiyue; Yang, Guang; Liu, Mengyu; Yang, Peng; Liu, Tao; Chemical communications (Cambridge, England) 59 (2023) 615–618; doi:10.1039/d2cc05882k

data_7131084
_publ_section_title
;
 Divergent upgrading pathways of sulfones with primary alcohols:
 nickel-catalyzed &#x3b1;-alkylation under N<sub>2</sub> and metal-free
 promoted &#x3b2;-olefination in open air.
;
_journal_issue                   5
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              615
_journal_page_last               618
_journal_paper_doi               10.1039/d2cc05882k
_journal_volume                  59
_journal_year                    2023
_chemical_formula_moiety         'C12 H18 O2 S'
_chemical_formula_sum            'C12 H18 O2 S'
_chemical_formula_weight         226.32
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2022-08-17
_audit_creation_method
;
  Olex2 1.2
  (compiled Apr 23 2013 17:54:37, GUI svn.r4466)
;
_audit_update_record
;
2022-09-20 deposited with the CCDC.	2022-12-09 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 91.873(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   19.9158(17)
_cell_length_b                   12.0713(9)
_cell_length_c                   10.9676(7)
_cell_measurement_reflns_used    3038
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.4640
_cell_measurement_theta_min      5.9170
_cell_volume                     2635.3(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
XS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0793
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9992
_diffrn_measured_fraction_theta_max 0.9825
_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    -65.00 -29.00   1.00    1.00    --    0.00 -58.00-179.00   36
  2  \w    -23.00  16.00   1.00    1.00    --    0.00 -58.00-179.00   39
  3  \w      0.00  75.00   1.00    1.87    --   54.00 -58.00-179.00   75
  4  \w     33.00 123.00   1.00    1.87    --   54.00  58.00 -38.00   90
  5  \w     41.00  98.00   1.00    1.87    --  108.00 -58.00-179.00   57
  6  \w     87.00 160.00   1.00    1.87    --  108.00  58.00 -38.00   73
  7  \w    -16.00  11.00   1.00    1.00    --    0.00 -77.00  30.00   27
  8  \w     29.00  69.00   1.00    1.00    --    0.00  58.00 -38.00   40
  9  \w    -17.00  24.00   1.00    1.00    --    0.00  58.00 -38.00   41
 10  \w      6.00  33.00   1.00    1.87    --   54.00 -99.00  30.00   27
 11  \w      7.00  59.00   1.00    1.87    --   54.00 -99.00-180.00   52
 12  \w     63.00  94.00   1.00    1.87    --   54.00 -99.00-180.00   31
 13  \w     32.00  77.00   1.00    1.87    --   54.00-125.00  60.00   45
 14  \w     46.00  96.00   1.00    1.87    --   54.00 -99.00  30.00   50
 15  \w    125.00 158.00   1.00    1.87    --  108.00  77.00-150.00   33
 16  \w     61.00 105.00   1.00    1.87    --  108.00 178.00  30.00   44
 17  \w     37.00 107.00   1.00    1.87    --  108.00-111.00  60.00   70
 18  \w    108.00 136.00   1.00    1.87    --  108.00 178.00  30.00   28
 19  \w     75.00 178.00   1.00    1.87    --  108.00  25.00 -90.00  103
 20  \w    104.00 143.00   1.00    1.87    --  108.00 111.00 -30.00   39
 21  \w     39.00 107.00   1.00    1.87    --  108.00 -91.00  90.00   68
 22  \w    108.00 175.00   1.00    1.87    --  108.00 111.00 -90.00   67
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0733863000
_diffrn_orient_matrix_UB_12      -0.0273179000
_diffrn_orient_matrix_UB_13      -0.0372340000
_diffrn_orient_matrix_UB_21      0.0246265000
_diffrn_orient_matrix_UB_22      -0.0834172000
_diffrn_orient_matrix_UB_23      -0.0949532000
_diffrn_orient_matrix_UB_31      -0.0005052000
_diffrn_orient_matrix_UB_32      -0.0926319000
_diffrn_orient_matrix_UB_33      0.0966603000
_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  0.0474
_diffrn_reflns_av_unetI/netI     0.0504
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            11609
_diffrn_reflns_theta_full        67.05
_diffrn_reflns_theta_max         67.06
_diffrn_reflns_theta_min         4.28
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.024
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.46424
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.141
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.444
_refine_diff_density_min         -0.394
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     302
_refine_ls_number_reflns         4705
_refine_ls_number_restraints     24
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.1043
_refine_ls_R_factor_gt           0.0613
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0976P)^2^+0.8986P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1627
_refine_ls_wR_factor_ref         0.1929
_reflns_number_gt                3262
_reflns_number_total             4705
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d2cc05882k2.cif
_cod_data_source_block           exp_983
_cod_depositor_comments
'Adding full bibliography for 7131082--7131084.cif.'
_cod_database_code               7131084
_chemical_oxdiff_formula         'C1 H1 O1 N1 S1'
_diffrn_oxdiff_digest_frames
;
01ce3a6a7516fb8a6c25c648136c6c674f00028a8ce
;
_diffrn_oxdiff_digest_hkl
;
010ab2c6600d1f5b2cea7fcb5097579ebfd9a2
;
_reflns_odcompleteness_completeness 99.92
_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
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C10-C9 = C11-C9 = C12-C9 = C10'-C9 = C11'-C9 = C12'-C9
 1.53 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
C10 \\sim C11 \\sim C12 \\sim C10' \\sim C11' \\sim C12': within 1.7A with sigma of 0.005 and sigma for terminal atoms of 0.005
4. Others
 Sof(C11')=Sof(H11D)=Sof(H11E)=Sof(H11F)=Sof(C10')=Sof(H10D)=Sof(H10E)=
 Sof(H10F)=Sof(C12')=Sof(H12D)=Sof(H12E)=Sof(H12F)=1-FVAR(1)
 Sof(C10)=Sof(H10A)=Sof(H10B)=Sof(H10C)=Sof(C11)=Sof(H11A)=Sof(H11B)=Sof(H11C)=
 Sof(C12)=Sof(H12A)=Sof(H12B)=Sof(H12C)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B), C19(H19A,H19B), C20(H20A,H20B)
5.b Me refined with riding coordinates:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C11'(H11D,H11E,
 H11F), C10'(H10D,H10E,H10F), C12'(H12D,H12E,H12F)
5.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C13(H13), C14(H14), C15(H15),
 C16(H16), C17(H17)
5.d Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C23(H23A,H23B,H23C), C24(H24A,H24B,H24C)
;
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.495
_oxdiff_exptl_absorpt_empirical_full_min 0.488