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_7131083
_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         'C15 H20 O2 S'
_chemical_formula_sum            'C15 H20 O2 S'
_chemical_formula_weight         264.37
_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             2022-08-15
_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                92.066(5)
_cell_angle_beta                 95.165(4)
_cell_angle_gamma                99.518(5)
_cell_formula_units_Z            4
_cell_length_a                   8.5020(4)
_cell_length_b                   13.0247(10)
_cell_length_c                   13.5023(7)
_cell_measurement_reflns_used    3685
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      69.8700
_cell_measurement_theta_min      7.9630
_cell_volume                     1466.64(15)
_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 0.9990
_diffrn_measured_fraction_theta_max 0.9788
_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    -31.00   5.00   1.00    1.00    --    0.00 107.00 147.00   36
  2  \w     23.00 100.00   1.00    1.00    --   54.00-107.00  49.00   77
  3  \w    113.00 142.00   1.00    1.00    --  108.00 107.00 147.00   29
  4  \w     47.00 106.00   1.00    1.00    --  108.00-107.00  49.00   59
  5  \w     39.00  66.00   1.00    1.00    --    0.00  57.00 -30.00   27
  6  \w     -4.00  30.00   1.00    1.00    --    0.00 -77.00   0.00   34
  7  \w      7.00  34.00   1.00    1.00    --    0.00  77.00  60.00   27
  8  \w    -21.00  21.00   1.00    1.00    --    0.00  57.00 -30.00   42
  9  \w     34.00 123.00   1.00    1.00    --   54.00  57.00-150.00   89
 10  \w     39.00 106.00   1.00    1.00    --   54.00  57.00   0.00   67
 11  \w    -12.00  60.00   1.00    1.00    --   54.00 -57.00  90.00   72
 12  \w    -15.00  18.00   1.00    1.00    --   54.00 -57.00  60.00   33
 13  \w     28.00 118.00   1.00    1.00    --   54.00  37.00 -30.00   90
 14  \w     55.00  80.00   1.00    1.00    --   54.00-125.00-180.00   25
 15  \w     68.00  93.00   1.00    1.00    --   54.00  57.00-120.00   25
 16  \w     14.00  75.00   1.00    1.00    --   54.00 -99.00 -90.00   61
 17  \w     39.00 142.00   1.00    1.00    --  108.00 -25.00 120.00  103
 18  \w    113.00 176.00   1.00    1.00    --  108.00 111.00 120.00   63
 19  \w     77.00 105.00   1.00    1.00    --  108.00-111.00 -30.00   28
 20  \w     83.00 145.00   1.00    1.00    --  108.00 178.00  60.00   62
 21  \w     80.00 170.00   1.00    1.00    --  108.00  25.00 -30.00   90
 22  \w     80.00 106.00   1.00    1.00    --  108.00 178.00-120.00   26
 23  \w     54.00 108.00   1.00    1.00    --  108.00-111.00-150.00   54
 24  \w     45.00  85.00   1.00    1.00    --  108.00 -91.00 -90.00   40
 25  \w    121.00 146.00   1.00    1.00    --  108.00 178.00-120.00   25
 26  \w     77.00 103.00   1.00    1.00    --  108.00 -91.00  60.00   26
 27  \w     36.00  68.00   1.00    1.00    --  108.00 -91.00  60.00   32
 28  \w    110.00 162.00   1.00    1.00    --  108.00  77.00-180.00   52
 29  \w     42.00 124.00   1.00    1.00    --  108.00 -63.00  60.00   82
 30  \w     45.00 127.00   1.00    1.00    --  108.00 -63.00-180.00   82
 31  \w     38.00 134.00   1.00    1.00    --  108.00 -25.00   0.00   96
;
_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      0.0483113000
_diffrn_orient_matrix_UB_12      0.1167693000
_diffrn_orient_matrix_UB_13      -0.0173732000
_diffrn_orient_matrix_UB_21      0.0669808000
_diffrn_orient_matrix_UB_22      0.0200967000
_diffrn_orient_matrix_UB_23      0.1101078000
_diffrn_orient_matrix_UB_31      0.1651041000
_diffrn_orient_matrix_UB_32      -0.0195749000
_diffrn_orient_matrix_UB_33      -0.0270942000
_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  0.0176
_diffrn_reflns_av_unetI/netI     0.0221
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10229
_diffrn_reflns_theta_full        67.06
_diffrn_reflns_theta_max         67.07
_diffrn_reflns_theta_min         4.64
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.893
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68182
_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    1.197
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.647
_refine_diff_density_min         -0.437
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     327
_refine_ls_number_reflns         5224
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0961
_refine_ls_R_factor_gt           0.0830
_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^)+(0.1384P)^2^+0.8680P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2398
_refine_ls_wR_factor_ref         0.2572
_reflns_number_gt                4204
_reflns_number_total             5224
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d2cc05882k2.cif
_cod_data_source_block           exp_964
_cod_depositor_comments
'Adding full bibliography for 7131082--7131084.cif.'
_cod_database_code               7131083
_chemical_oxdiff_formula         'C1 H1 O1 N1 S1'
_diffrn_oxdiff_digest_frames
;
01cd06dd08185105c1d31a0ad35ddf05a30002777a9
;
_diffrn_oxdiff_digest_hkl
;
0110dadb90730831ccf6ad4d61deb86f18fade
;
_reflns_odcompleteness_completeness 99.90
_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. Rigid bond restraints
 C15, C14
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
3.a Ternary CH refined with riding coordinates:
 C7(H7), C22(H22)
3.b Secondary CH2 refined with riding coordinates:
 C30(H30A,H30B), C28(H28A,H28B), C29(H29A,H29B), C26(H26A,H26B), C13(H13A,
 H13B), C14(H14A,H14B), C12(H12A,H12B), C15(H15A,H15B), C11(H11A,H11B),
 C27(H27A,H27B)
3.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C9(H9), C1(H1), C24(H24), C20(H20), C4(H4), C3(H3), C16(H16),
 C19(H19), C18(H18), C17(H17), C2(H2)
3.d Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C23(H23A,H23B,H23C)
;
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.408
_oxdiff_exptl_absorpt_empirical_full_min 0.637