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_7160420
_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_absolute_configuration ad
_chemical_formula_moiety         'C19 H19 N3 O4'
_chemical_formula_sum            'C19 H19 N3 O4'
_chemical_formula_weight         353.37
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2024-07-08
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2024-07-09 deposited with the CCDC.	2025-03-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.7943(3)
_cell_length_b                   14.7109(3)
_cell_length_c                   17.1758(4)
_cell_measurement_reflns_used    13288
_cell_measurement_temperature    99.98(10)
_cell_measurement_theta_max      73.1170
_cell_measurement_theta_min      4.3900
_cell_volume                     3485.43(13)
_computing_cell_refinement       'CrysAlisPro 1.171.43.92a (Rigaku OD, 2023)'
_computing_data_collection
'CrysAlisPro system (CCD 43.92a 64-bit (release 05-10-2023))'
_computing_data_reduction        'CrysAlisPro 1.171.43.92a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.98(10)
_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 0.980
_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     70.00 103.00   0.50    0.22    --   99.00 -77.00-120.00   66
  2  \w     49.00  91.00   0.50    0.22    --   99.00 -77.00-150.00   84
  3  \w     26.00  57.00   0.50    0.22    --   99.00 -77.00-120.00   62
  4  \w     31.00  70.00   0.50    0.22    --   99.00 -61.00 -90.00   78
  5  \w     27.00  52.00   0.50    0.22    --   99.00 -45.00 -30.00   50
  6  \w     27.00  53.00   0.50    0.22    --   99.00 -45.00   0.00   52
  7  \w     26.00  71.00   0.50    0.22    --   99.00 -61.00   0.00   90
  8  \w     27.00  52.00   0.50    0.22    --   99.00 -45.00-120.00   50
  9  \w     34.00  73.00   0.50    0.22    --   99.00 -61.00  30.00   78
 10  \w     27.00  52.00   0.50    0.22    --   99.00 -45.00  60.00   50
 11  \w     27.00  52.00   0.50    0.22    --   99.00 -45.00 120.00   50
 12  \w     47.00  73.00   0.50    0.22    --   99.00 -61.00 150.00   52
 13  \w     32.00  85.00   0.50    0.06    --   45.37  37.00-150.00  106
 14  \w     87.00 118.00   0.50    0.06    --   45.37  37.00-150.00   62
 15  \w     27.00  52.00   0.50    0.22    --   99.00 -45.00 -90.00   50
 16  \w     32.00  74.00   0.50    0.22    --   99.00 -94.00-120.00   84
 17  \w     33.00  93.00   0.50    0.22    --   99.00-110.00-162.00  120
 18  \w     29.00 110.00   0.50    0.22    --   99.00-125.00-120.00  162
 19  \w     73.00 120.00   0.50    0.22    --   99.00-137.00 124.00   94
 20  \w     29.00  66.00   0.50    0.22    --   99.00-137.00 124.00   74
 21  \w   -120.00 -45.00   0.50    0.06    --  -45.37 -16.00 -13.00  150
 22  \w   -175.00-102.00   0.50    0.22    --  -99.00 -16.00 -13.00  146
 23  \w    -61.00 -27.00   0.50    0.22    --  -99.00  61.00 120.00   68
 24  \w    -65.00 -26.00   0.50    0.22    --  -99.00  61.00 -30.00   78
 25  \w    -25.00  29.00   0.50    0.06    --  -45.37  37.00 -90.00  108
 26  \w    -83.00 -48.00   0.50    0.06    --  -45.37 125.00 -60.00   70
 27  \w    -65.00 -36.00   0.50    0.22    --  -99.00 125.00-120.00   58
 28  \w   -101.00 -76.00   0.50    0.22    --  -99.00 125.00-120.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0451927000
_diffrn_orient_matrix_UB_12      -0.0070242000
_diffrn_orient_matrix_UB_13      0.0818054000
_diffrn_orient_matrix_UB_21      0.0994599000
_diffrn_orient_matrix_UB_22      -0.0209280000
_diffrn_orient_matrix_UB_23      -0.0367130000
_diffrn_orient_matrix_UB_31      0.0234098000
_diffrn_orient_matrix_UB_32      0.1023341000
_diffrn_orient_matrix_UB_33      -0.0019490000
_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  0.0519
_diffrn_reflns_av_unetI/netI     0.0433
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            25393
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.705
_diffrn_reflns_theta_min         3.956
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.793
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91265
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.92a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_description       block
_exptl_crystal_F_000             1488
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.579
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details
;
 Flack x determined using 2395 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     509
_refine_ls_number_reflns         6847
_refine_ls_number_restraints     479
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0551
_refine_ls_R_factor_gt           0.0468
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0728P)^2^+0.7210P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1216
_refine_ls_wR_factor_ref         0.1294
_reflns_Friedel_coverage         0.777
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.961
_reflns_number_gt                6034
_reflns_number_total             6847
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob00402k2.cif
_cod_data_source_block           a-4-2no
_cod_depositor_comments
'Adding full bibliography for 7160419--7160421.cif.'
_cod_database_code               7160420
_shelx_shelxl_version_number     2018/3
_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, All O(H) groups
2. Restrained distances
 O6-C48 \\sim O6A-C48
 with sigma of 0.02
 O5-C48 \\sim O5A-C48
 with sigma of 0.02
 O3-C14 \\sim O3A-C14
 with sigma of 0.02
 O4-C14 \\sim O4A-C14
 with sigma of 0.02
3. Rigid bond restraints
 C48, O5A
 with sigma for 1-2 distances of 0.0008 and sigma for 1-3 distances of 0.0008
4. Uiso/Uaniso restraints and constraints
O5A \\sim C48: within 2A with sigma of 0.0008 and sigma for terminal atoms of
0.0016 within 2A
5. Rigid body (RIGU) restrains
 O5A, O6, C48, O5, C47, O6A, N4, C46, C43, C45, H46, C34, C44, H45, N5, N6,
 H34, H44, C28, C35, C29, C32, O7, O8, C36, C40, H29, C30, C31, H32A, H32B, H7,
 H36, C37, C39, H40, H30A, H30B, H31A, H31B, H37, C38, C41, H38, H41A, H41B,
 H41C
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.008
 O4, O1, C15, C16, N1, H16, C17, N2, C1, C8, H17A, H17B, C18, O2, C19, C2, C6,
 H8, C9, H18A, H18B, H2, H19A, H19B, H2A, C3, C5, H6, N3, C10, C4, C7, H5, C13,
 H10, C11, H4, H7A, H7B, H7C, C12, C14, H11, H12, O4A, O3A, O3
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.008
6. Others
 Sof(O5A)=Sof(O6A)=1-FVAR(1)
 Sof(O6)=Sof(O5)=FVAR(1)
 Sof(O4A)=Sof(O3A)=1-FVAR(2)
 Sof(O3)=Sof(O4)=FVAR(2)
7.a Ternary CH refined with riding coordinates:
 C8(H8), C16(H16), C29(H29), C34(H34)
7.b Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C18(H18A,H18B), C19(H19A,H19B), C30(H30A,H30B), C31(H31A,
 H31B), C32(H32A,H32B)
7.c Aromatic/amide H refined with riding coordinates:
 C2(H2A), C4(H4), C5(H5), C6(H6), C10(H10), C11(H11), C12(H12), C36(H36),
 C37(H37), C38(H38), C40(H40), C44(H44), C45(H45), C46(H46)
7.d Tetrahedral OH refined with riding coordinates:
 O2(H2), O7(H7)
7.e Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C41(H41A,H41B,H41C)
;
_shelx_res_checksum              56782
_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 1.250
_oxdiff_exptl_absorpt_empirical_full_min 0.787