Ring-opening decarbonylative C(sp3)–C(sp3) cross-electrophile coupling of cyclic imides with unactivated alkyl chlorides
Lentelink, Niklas J.; Pânzar, Peter M. F.; Rowlinson, Nathalie A. V.; Morandi, Bill; Chemical Science  (2026) –; doi:10.1039/D6SC00815A

data_1576861
_publ_section_title
;
 Ring-opening decarbonylative C(sp<sup>3</sup>)-C(sp<sup>3</sup>)
 cross-electrophile coupling of cyclic imides with unactivated alkyl
 chlorides.
;
_journal_issue                   17
_journal_name_full               'Chemical science'
_journal_page_first              8479
_journal_page_last               8485
_journal_paper_doi               10.1039/d6sc00815a
_journal_volume                  17
_journal_year                    2026
_chemical_formula_moiety         'C26 H37 N3 Ni O3'
_chemical_formula_sum            'C26 H37 N3 Ni O3'
_chemical_formula_weight         498.29
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc2przwb
_audit_creation_date             2025-05-14
_audit_creation_method
;
Olex2 1.5
(compiled 2025.04.05 svn.rf049d14d for OlexSys, GUI svn.r7224)
;
_audit_update_record
;
2025-10-15 deposited with the CCDC.	2026-02-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.606(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.3948(2)
_cell_length_b                   12.1968(2)
_cell_length_c                   20.7449(4)
_cell_measurement_reflns_used    7748
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      70.7070
_cell_measurement_theta_min      4.2060
_cell_volume                     2593.23(8)
_computing_cell_refinement       'CrysAlisPro 1.171.43.143a (Rigaku OD, 2024)'
_computing_data_collection
'CrysAlisPro system (CCD 43.143a 64-bit (release 25-10-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.143a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(1)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.954
_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    -95.00 -68.00   0.50    3.50    --  -50.00 -34.00  55.71   54
  2  \w   -108.00 -77.00   0.50    3.50    --  -62.00 -54.00  11.09   62
  3  \w    -49.00 -18.00   0.50    3.50    --  -62.00  62.00 -14.92   62
  4  \w   -109.00 -78.00   0.50    3.50    --  -62.00 -39.00  40.83   62
  5  \w   -112.00 -81.00   0.50    3.50    --  -66.00 -54.00-179.69   62
  6  \w   -111.00 -80.00   0.50    3.50    --  -66.00 -57.00-137.26   62
  7  \w    -95.00 -25.00   0.50    3.50    --  -69.39 125.00   0.00  140
  8  \w   -118.00 -84.00   0.50    3.50    --  -70.00 -42.00 106.75   68
  9  \w   -113.00 -87.00   0.50    3.50    --  -70.00 -26.00 126.50   52
 10  \w   -113.00 -83.00   0.50    3.50    --  -70.00 -64.00 -86.13   60
 11  \w     30.00  78.00   0.50    3.50    --   70.78 -95.00 120.00   96
 12  \w    -57.00 -31.00   0.50    3.50    --  -72.64  68.00-127.64   52
 13  \w   -114.00 -83.00   0.50    3.50    --  -72.64 -18.00 -63.04   62
 14  \w   -114.00 -87.00   0.50    3.50    --  -72.64 -20.00 130.74   54
 15  \w    -66.00 -35.00   0.50    3.50    --  -72.64  76.00  21.64   62
 16  \w    -59.00 -32.00   0.50    3.50    --  -72.64  69.00 -53.51   54
 17  \w   -114.00 -87.00   0.50    3.50    --  -72.64 -21.00 -71.47   54
 18  \w    -66.00 -34.00   0.50    3.50    --  -72.64  75.00 115.97   64
 19  \w   -119.00 -92.00   0.50    3.50    --  -74.00 -34.00 -95.86   54
 20  \w   -120.00 -92.00   0.50    3.50    --  -74.00 -33.00 -20.53   56
 21  \w   -119.00 -92.00   0.50    3.50    --  -74.00 -35.00 -69.89   54
 22  \w   -117.00 -90.00   0.50    8.00    --  -75.17 -21.00  17.71   54
 23  \w   -100.00 -35.00   0.50    8.00    --  -75.17 125.00  33.68  130
 24  \w   -100.00 -35.00   0.50    8.00    --  -75.17 125.00  33.68  130
 25  \w   -116.00 -91.00   0.50    8.00    --  -75.17 -19.00  -6.09   50
 26  \w   -118.00 -93.00   0.50    8.00    --  -75.17 -23.00-133.44   50
 27  \w     91.00 116.00   0.50    8.00    --   75.17  22.00 -81.64   50
 28  \w     90.00 115.00   0.50    8.00    --   75.17  21.00 124.73   50
 29  \w     46.00  81.00   0.50    8.00    --   77.85 -95.00  60.00   70
 30  \w     42.00  85.00   0.50    8.00    --   77.85 -95.00 120.00   86
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix-Arc 150'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0001345000
_diffrn_orient_matrix_UB_12      0.0222225000
_diffrn_orient_matrix_UB_13      -0.0731191000
_diffrn_orient_matrix_UB_21      -0.1431710000
_diffrn_orient_matrix_UB_22      0.0376767000
_diffrn_orient_matrix_UB_23      -0.0080341000
_diffrn_orient_matrix_UB_31      0.0455002000
_diffrn_orient_matrix_UB_32      0.1185146000
_diffrn_orient_matrix_UB_33      0.0162839000
_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  0.0498
_diffrn_reflns_av_unetI/netI     0.0406
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.954
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            22020
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.569
_diffrn_reflns_theta_min         4.220
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.319
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.883
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.143a (Rigaku Oxford Diffraction, 2024)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_description       plate
_exptl_crystal_F_000             1064
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.046
_exptl_crystal_size_min          0.024
_refine_diff_density_max         0.782
_refine_diff_density_min         -0.440
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         5043
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0614
_refine_ls_R_factor_gt           0.0446
_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^)+(0.0731P)^2^+0.7635P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1139
_refine_ls_wR_factor_ref         0.1234
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3960
_reflns_number_total             5043
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d6sc00815a2.cif
_cod_data_source_block           bm080525_1_1
_cod_depositor_comments
'Adding full bibliography for 1576860--1576861.cif.'
_cod_database_code               1576861
_shelx_shelxl_version_number     2019/3
_chemical_oxdiff_formula         C27H39N3NiO2
_shelx_estimated_absorpt_t_max   0.974
_shelx_estimated_absorpt_t_min   0.837
_diffrn_oxdiff_ac3_digest_hkl    41bf95e4f9698c1414f723681ef732fe299950
_diffrn_oxdiff_digest_hkl
;
43dad43f4ad3b7058686a3258daf980797a874
;
_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.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B)
2.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C16(H16), C19(H19), C25(H25), C26(H26)
2.c Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C13(H13A,H13B,H13C),
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C22(H22A,H22B,H22C), C23(H23A,H23B,
 H23C), C24(H24A,H24B,H24C)
;
_shelx_res_checksum              28984
_olex2_date_sample_data_collection 2025-05-13
_olex2_date_sample_submission    2025-05-12
_olex2_submission_original_sample_id bm080525_1_1
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.720
_oxdiff_exptl_absorpt_empirical_full_min 0.643