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_7160421
_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         'C31 H39 Co N4 O'
_chemical_formula_sum            'C31 H40 Co N4 O'
_chemical_formula_weight         543.60
_chemical_properties_physical
Air-sensitive,Moisture-sensitive,Hygroscopic,Deliquescent,Heat-sensitive
_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   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2024-07-08
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_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                   10.7954(14)
_cell_length_b                   11.5740(15)
_cell_length_c                   47.361(6)
_cell_measurement_reflns_used    9962
_cell_measurement_temperature    170.00
_cell_measurement_theta_max      57.384
_cell_measurement_theta_min      3.247
_cell_volume                     5917.6(13)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      170.00
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'zju Bruker D8 Venture'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0812
_diffrn_reflns_av_unetI/netI     0.0751
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       61
_diffrn_reflns_limit_l_min       -61
_diffrn_reflns_number            82640
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         60.625
_diffrn_reflns_theta_min         3.247
_diffrn_source_current           3.57
_diffrn_source_power             0.24954300000000001
_diffrn_source_voltage           69.9
_exptl_absorpt_coefficient_mu    3.317
_exptl_absorpt_correction_T_max  0.7519
_exptl_absorpt_correction_T_min  0.6038
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1326 before and 0.0942 after correction.
The Ratio of minimum to maximum transmission is 0.8030.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.220
_exptl_crystal_description       plate
_exptl_crystal_F_000             2312
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: hexane'
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.290
_refine_diff_density_min         -0.370
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.035(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     684
_refine_ls_number_reflns         13311
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.004
_refine_ls_R_factor_all          0.0570
_refine_ls_R_factor_gt           0.0427
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0551P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1018
_refine_ls_wR_factor_ref         0.1078
_reflns_Friedel_coverage         0.776
_reflns_Friedel_fraction_full    0.963
_reflns_Friedel_fraction_max     0.966
_reflns_number_gt                10637
_reflns_number_total             13311
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob00402k2.cif
_cod_data_source_block           240708_zcg03123_0m
_cod_depositor_comments
'Adding full bibliography for 7160419--7160421.cif.'
_cod_database_code               7160421
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.879
_shelx_estimated_absorpt_t_min   0.712
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.965(5)
 0.035(5)
2. 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
3.a Rotating group:
 O1(H1), O2(H2)
3.b Ternary CH refined with riding coordinates:
 C29(H29), C60(H60), C57(H57), C10(H10), C41(H41), C42(H42), C11(H11), C26(H26)
3.c Secondary CH2 refined with riding coordinates:
 C40(H40A,H40B), C9(H9A,H9B)
3.d Aromatic/amide H refined with riding coordinates:
 C54(H54), C15(H15), C39(H39), C53(H53), C55(H55), C19(H19), C22(H22),
 C18(H18), C7(H7), C6(H6), C8(H8), C16(H16), C46(H46), C17(H17), C23(H23),
 C37(H37), C24(H24), C50(H50), C38(H38), C48(H48), C49(H49), C47(H47)
3.e Idealised Me refined as rotating group:
 C28(H28A,H28B,H28C), C1(H1A,H1B,H1C), C30(H30A,H30B,H30C), C61(H61A,H61B,
 H61C), C32(H32A,H32B,H32C), C62(H62A,H62B,H62C), C31(H31A,H31B,H31C), C27(H27A,
 H27B,H27C), C44(H44A,H44B,H44C), C43(H43A,H43B,H43C), C12(H12A,H12B,H12C),
 C59(H59A,H59B,H59C), C13(H13A,H13B,H13C), C58(H58A,H58B,H58C)
;
_shelx_res_checksum              61659
_olex2_submission_special_instructions 'No special instructions were received'