Construction of multi-functionalized carbon chains by Ni-catalyzed carbosulfonylation of butadiene.
Liu, Yan; Zhang, Xiang-Xin; Li, Xue-Ting; Xu, Su-Yang; Ji, Ding-Wei; Chen, Qing-An; Organic & biomolecular chemistry 23 (2025) 3619–3628; doi:10.1039/d5ob00402k

data_7160419
_publ_section_title
;
 Construction of multi-functionalized carbon chains by Ni-catalyzed
 carbosulfonylation of butadiene.
;
_journal_issue                   15
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3619
_journal_page_last               3628
_journal_paper_doi               10.1039/d5ob00402k
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C16 H16 O2 S'
_chemical_formula_sum            'C16 H16 O2 S'
_chemical_formula_weight         272.35
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_block_doi                 10.5517/ccdc.csd.cc2jdf6l
_audit_creation_date             2024-01-22
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2024-02-27 deposited with the CCDC.	2025-03-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 108.564(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.78749(19)
_cell_length_b                   15.2412(2)
_cell_length_c                   10.1184(2)
_cell_measurement_reflns_used    8563
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      76.6890
_cell_measurement_theta_min      4.8230
_cell_volume                     1430.86(5)
_computing_cell_refinement       'CrysAlisPro 1.171.43.101a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.43.101a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.43.101a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.977
_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     33.00  64.00   0.50    0.05    --   48.96 -57.00  90.00   62
  2  \w    -12.00  31.00   0.50    0.05    --   48.96 -57.00  90.00   86
  3  \w    -22.00  26.00   0.50    0.05    --   48.96 -19.00  90.00   96
  4  \w    -24.00  26.00   0.50    0.05    --   48.96 -19.00 150.00  100
  5  \w    -25.00  43.00   0.50    0.05    --   48.96 -38.00 -30.00  136
  6  \w    -15.00  24.00   0.50    0.05    --   48.96 -19.00-120.00   78
  7  \w    -26.00  21.00   0.50    0.05    --   48.96 -19.00-150.00   94
  8  \w    -19.00  64.00   0.50    0.05    --   48.96 -57.00-150.00  166
  9  \w     43.00 112.00   0.50    0.20    --  107.98-125.00-180.00  138
 10  \w     41.00  90.00   0.50    0.20    --  107.98 -77.00 -60.00   98
 11  \w     48.00  94.00   0.50    0.20    --  107.98-125.00 -30.00   92
 12  \w     80.00 105.00   0.50    0.20    --  107.98 -77.00   0.00   50
 13  \w     37.00  86.00   0.50    0.20    --  107.98 -95.00  30.00   98
 14  \w     40.00  72.00   0.50    0.20    --  107.98 -77.00 150.00   64
 15  \w     38.00  64.00   0.50    0.20    --  107.98 -61.00  90.00   52
 16  \w     35.00  71.00   0.50    0.20    --  107.98 -61.00  60.00   72
 17  \w     39.00  64.00   0.50    0.20    --  107.98 -61.00-150.00   50
 18  \w     90.00 133.00   0.50    0.20    --  107.98  15.00  30.00   86
 19  \w    137.00 177.00   0.50    0.20    --  107.98  15.00  30.00   80
 20  \w    100.00 154.00   0.50    0.20    --  107.98  77.00-150.00  108
 21  \w     96.00 178.00   0.50    0.20    --  107.98  15.00 -60.00  164
 22  \w     81.00 117.00   0.50    0.05    --   48.96 125.00 150.00   72
 23  \w    -64.00 -38.00   0.50    0.20    -- -105.48  61.00  90.00   52
 24  \w   -104.00 -36.00   0.50    0.20    -- -105.48 125.00  60.00  136
 25  \w    -68.00 -38.00   0.50    0.20    -- -105.48 139.00 -67.89   60
 26  \w   -122.00 -71.00   0.50    0.20    -- -105.48 139.00 -67.89  102
 27  \w   -121.00 -51.00   0.50    0.20    -- -105.48 138.00-156.96  140
 28  \w    -72.00 -46.00   0.50    0.05    --  -46.46 125.00-120.00   52
 29  \w    -60.00 -35.00   0.50    0.20    -- -105.48 125.00   0.00   50
 30  \w   -111.00 -83.00   0.50    0.20    -- -105.48 125.00   0.00   56
 31  \w   -111.00 -85.00   0.50    0.20    -- -105.48 125.00 120.00   52
 32  \w   -176.00-150.00   0.50    0.20    -- -105.48 -15.00 150.00   52
 33  \w   -145.00 -93.00   0.50    0.20    -- -105.48 -15.00 150.00  104
 34  \w   -174.00 -89.00   0.50    0.20    -- -105.48-125.00  90.00  170
 35  \w   -115.00 -90.00   0.50    0.20    -- -105.48 -30.00 -60.00   50
 36  \w   -174.00-135.00   0.50    0.20    -- -105.48 -30.00 -60.00   78
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1199950000
_diffrn_orient_matrix_UB_12      -0.0411541000
_diffrn_orient_matrix_UB_13      -0.0481040000
_diffrn_orient_matrix_UB_21      0.0683966000
_diffrn_orient_matrix_UB_22      -0.0400289000
_diffrn_orient_matrix_UB_23      0.1459828000
_diffrn_orient_matrix_UB_31      -0.0921208000
_diffrn_orient_matrix_UB_32      -0.0832427000
_diffrn_orient_matrix_UB_33      -0.0464700000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0349
_diffrn_reflns_av_unetI/netI     0.0259
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            14904
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.481
_diffrn_reflns_theta_min         5.449
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.964
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90754
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.101a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_description       block
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.351
_refine_diff_density_min         -0.508
_refine_diff_density_rms         0.099
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2936
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0626
_refine_ls_R_factor_gt           0.0565
_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^)+(0.1022P)^2^+0.2108P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1562
_refine_ls_wR_factor_ref         0.1644
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2487
_reflns_number_total             2936
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob00402k2.cif
_cod_data_source_block           1002-0122_auto
_cod_depositor_comments
'Adding full bibliography for 7160419--7160421.cif.'
_cod_database_code               7160419
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.798
_shelx_estimated_absorpt_t_min   0.707
_diffrn_oxdiff_digest_frames
;
0162839c33c6544cb8aab7240d5ea8c1a6000626823
;
_diffrn_oxdiff_digest_hkl
;
01b0c28d0d3de0d5ee13efe3726d93b22d2599
;
_reflns_odcompleteness_completeness 100.00
_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 Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C7(H7), C8(H8), C9(H9), C10(H10), C11(H11), C14(H14),
 C15(H15), C16(H16), C17(H17), C18(H18)
;
_shelx_res_checksum              19106
_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 1.379
_oxdiff_exptl_absorpt_empirical_full_min 0.720