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_7131082
_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         'C19 H26 O3 S'
_chemical_formula_sum            'C19 H26 O3 S'
_chemical_formula_weight         334.46
_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
_atom_sites_solution_secondary   difmap
_audit_creation_date             2022-07-31
_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                112.511(7)
_cell_angle_beta                 96.462(6)
_cell_angle_gamma                97.113(6)
_cell_formula_units_Z            2
_cell_length_a                   6.1676(5)
_cell_length_b                   11.8368(9)
_cell_length_c                   13.6151(10)
_cell_measurement_reflns_used    2172
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.4540
_cell_measurement_theta_min      4.0760
_cell_volume                     897.19(13)
_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 0.9991
_diffrn_measured_fraction_theta_max 0.9774
_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    -46.00 -20.00   1.00    1.00    --    0.00 132.00   1.00   26
  2  \w    -48.00 -21.00   1.00    1.00    --    0.00 137.00 178.00   27
  3  \w     31.00 105.00   1.00    1.00    --   54.00-132.00 -68.00   74
  4  \w     52.00  77.00   1.00    1.00    --   54.00-137.00 115.00   25
  5  \w    110.00 135.00   1.00    1.00    --  108.00 137.00 178.00   25
  6  \w    112.00 137.00   1.00    1.00    --  108.00 132.00   1.00   25
  7  \w     82.00 118.00   1.00    1.00    --  108.00-132.00 -68.00   36
  8  \w     43.00  79.00   1.00    1.00    --  108.00-132.00 -68.00   36
  9  \w    -17.00  24.00   1.00    1.00    --    0.00 -77.00-150.00   41
 10  \w    -14.00  11.00   1.00    1.00    --    0.00 -77.00 -90.00   25
 11  \w    -19.00  14.00   1.00    1.00    --    0.00 -77.00-180.00   33
 12  \w     90.00 119.00   1.00    1.00    --   54.00  57.00 -30.00   29
 13  \w     28.00  62.00   1.00    1.00    --   54.00-125.00 120.00   34
 14  \w    -15.00  70.00   1.00    1.00    --   54.00 -57.00 -60.00   85
 15  \w    -15.00 107.00   1.00    1.00    --   54.00   0.00 150.00  122
 16  \w     -3.00  65.00   1.00    1.00    --   54.00 -57.00 120.00   68
 17  \w    123.00 155.00   1.00    1.00    --  108.00 111.00 -90.00   32
 18  \w    109.00 155.00   1.00    1.00    --  108.00 111.00-150.00   46
 19  \w     64.00 104.00   1.00    1.00    --  108.00 -77.00  60.00   40
 20  \w     75.00 140.00   1.00    1.00    --  108.00 178.00 120.00   65
 21  \w     90.00 178.00   1.00    1.00    --  108.00  37.00 -60.00   88
 22  \w    145.00 177.00   1.00    1.00    --  108.00  37.00 -30.00   32
 23  \w     91.00 119.00   1.00    1.00    --  108.00  63.00   0.00   28
 24  \w    115.00 176.00   1.00    1.00    --  108.00 111.00 -30.00   61
 25  \w     59.00 127.00   1.00    1.00    --  108.00 -63.00-120.00   68
 26  \w     74.00 104.00   1.00    1.00    --  108.00 -91.00 -90.00   30
 27  \w     51.00 100.00   1.00    1.00    --  108.00-111.00-180.00   49
 28  \w     36.00  63.00   1.00    1.00    --  108.00 -91.00 -90.00   27
 29  \w     91.00 174.00   1.00    1.00    --  108.00  50.00  30.00   83
 30  \w    127.00 152.00   1.00    1.00    --  108.00  63.00   0.00   25
 31  \w    103.00 176.00   1.00    1.00    --  108.00  77.00-120.00   73
 32  \w     37.00  65.00   1.00    1.00    --  108.00 -91.00-180.00   28
 33  \w     89.00 140.00   1.00    1.00    --  108.00  37.00 -30.00   51
 34  \w     39.00 121.00   1.00    1.00    --  108.00-137.00 115.00   82
;
_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      0.0573736000
_diffrn_orient_matrix_UB_12      -0.0937421000
_diffrn_orient_matrix_UB_13      -0.1041764000
_diffrn_orient_matrix_UB_21      0.1761247000
_diffrn_orient_matrix_UB_22      -0.0344199000
_diffrn_orient_matrix_UB_23      0.0679287000
_diffrn_orient_matrix_UB_31      -0.1761821000
_diffrn_orient_matrix_UB_32      -0.1027361000
_diffrn_orient_matrix_UB_33      0.0024876000
_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  0.0327
_diffrn_reflns_av_unetI/netI     0.0372
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6248
_diffrn_reflns_theta_full        67.05
_diffrn_reflns_theta_max         67.06
_diffrn_reflns_theta_min         3.57
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.696
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.45500
_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    1.238
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.238
_refine_diff_density_min         -0.393
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3198
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0742
_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^)+(0.1182P)^2^+0.1164P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1682
_refine_ls_wR_factor_ref         0.1884
_reflns_number_gt                2530
_reflns_number_total             3198
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d2cc05882k2.cif
_cod_data_source_block           exp_949
_cod_depositor_comments
'Adding full bibliography for 7131082--7131084.cif.'
_cod_original_cell_volume        897.20(12)
_cod_database_code               7131082
_chemical_oxdiff_formula         'C1 H1 O1 N1 S1'
_diffrn_oxdiff_digest_frames
;
01c4c80430fd04e867a4ac6991d7f8eef7000283abf
;
_diffrn_oxdiff_digest_hkl
;
01480ad69e3a455c3b28ae178162836bae5f71
;
_reflns_odcompleteness_completeness 99.91
_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:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C10(H10A,H10B), C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B),
 C15(H15A,H15B), C19(H19A,H19B), C20(H20A,H20B), C22(H22A,H22B), C23(H23A,H23B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C16(H16)
;
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.897
_oxdiff_exptl_absorpt_empirical_full_min 0.491