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_1576860
_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_absolute_configuration ad
_chemical_formula_moiety         'C20 H24 N2 Ni O2'
_chemical_formula_sum            'C20 H24 N2 Ni O2'
_chemical_formula_weight         383.12
_space_group_crystal_system      orthorhombic
_space_group_IT_number           43
_space_group_name_Hall           'F 2 -2d'
_space_group_name_H-M_alt        'F d d 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc2przv9
_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.	2026-02-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   22.0314(3)
_cell_length_b                   20.8413(3)
_cell_length_c                   8.44160(10)
_cell_measurement_reflns_used    10516
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      70.9460
_cell_measurement_theta_min      5.8210
_cell_volume                     3876.07(9)
_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 0.997
_diffrn_measured_fraction_theta_max 0.965
_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    -63.00 -36.00   0.50    0.07    --  -72.64  72.00-112.58   54
  2  \w    -68.00 -43.00   0.50    0.07    --  -72.64  78.00 -55.91   50
  3  \w    -59.00 -34.00   0.50    0.07    --  -72.64  70.00 -46.25   50
  4  \w    -46.00 -19.00   0.50    0.07    --  -62.00  62.00 -44.15   54
  5  \w    -45.00 -19.00   0.50    0.07    --  -62.00  62.00 -23.83   52
  6  \w    -47.00 -21.00   0.50    0.07    --  -62.00  62.00  39.94   52
  7  \w    -59.00 -34.00   0.50    0.07    --  -72.64  72.00  17.17   50
  8  \w    -63.00 -38.00   0.50    0.07    --  -72.64  72.00  -2.92   50
  9  \w    -35.00  -9.00   0.50    0.07    --  -54.00  52.00  74.00   52
 10  \w    -38.00 -12.00   0.50    0.07    --  -58.00  54.00 -85.21   52
 11  \w    -35.00 -10.00   0.50    0.07    --  -54.00  52.00-122.87   50
 12  \w    -31.00  -5.00   0.50    0.07    --  -50.00  50.00-166.45   52
 13  \w     -6.00  19.00   0.50    0.07    --  -14.00  73.00  52.99   50
 14  \w      1.00  26.00   0.50    0.07    --   -6.00  75.00 155.82   50
 15  \w     57.00  82.00   0.50    0.07    --   42.00  55.00 145.58   50
 16  \w     65.00  90.00   0.50    0.07    --   50.00  55.00 160.73   50
 17  \w     57.00  82.00   0.50    0.07    --   42.00  54.00 128.04   50
 18  \w     57.00  82.00   0.50    0.07    --   42.00  55.00 108.97   50
 19  \w     65.00  90.00   0.50    0.07    --   50.00  55.00  89.19   50
 20  \w     65.00  90.00   0.50    0.07    --   50.00  54.00 100.69   50
 21  \w     56.00  82.00   0.50    0.07    --   38.00  52.00  70.45   52
 22  \w     90.00 115.00   0.50    0.07    --   72.89  26.00-132.40   50
 23  \w     88.00 117.00   0.50    0.07    --   72.89  24.00 -91.40   58
 24  \w     85.00 111.00   0.50    0.07    --   72.89  17.00-138.06   52
 25  \w     64.00  94.00   0.50    0.07    --   67.93-125.00  30.00   60
 26  \w     69.00  94.00   0.50    0.07    --   67.93-125.00  90.00   50
 27  \w     75.00 100.00   0.50    0.07    --   77.85-125.00  60.00   50
 28  \w     23.00  53.00   0.50    0.07    --   67.93-125.00  30.00   60
 29  \w     33.00  59.00   0.50    0.07    --   77.85-125.00  60.00   52
 30  \w     29.00  55.00   0.50    0.07    --   67.93-125.00  90.00   52
 31  \w     26.00  60.00   0.50    0.07    --   67.93-125.00 150.00   68
 32  \w     64.00  89.00   0.50    0.07    --   67.93-125.00 150.00   50
 33  \w     38.00  78.00   0.50    0.07    --   77.85 -95.00 150.00   80
 34  \w     43.00  85.00   0.50    0.07    --   77.85 -95.00  90.00   84
 35  \w     30.00  55.00   0.50    0.07    --   70.78 -95.00 -90.00   50
 36  \w    -68.00 -42.00   0.50    0.07    --  -26.00 -49.00  83.00   52
 37  \w    -53.00 -28.00   0.50    0.07    --  -14.00 -60.00  70.54   50
 38  \w    -52.00 -27.00   0.50    0.07    --  -14.00 -62.00  35.52   50
 39  \w    -77.00 -51.00   0.50    0.07    --  -34.00 -55.00 124.69   52
 40  \w    -52.00 -27.00   0.50    0.07    --  -14.00 -62.00  13.76   50
 41  \w    -60.00 -35.00   0.50    0.07    --  -18.00 -55.00 -23.06   50
 42  \w    -75.00 -49.00   0.50    0.07    --  -34.00 -55.00  -5.52   52
 43  \w    -64.00 -39.00   0.50    0.07    --  -18.00 -54.00  10.36   50
 44  \w    -90.00 -65.00   0.50    0.07    --  -50.00 -55.00  63.22   50
 45  \w    -93.00 -68.00   0.50    0.07    --  -50.00 -52.00 144.62   50
 46  \w    -76.00 -50.00   0.50    0.07    --  -30.00 -54.00  78.20   52
 47  \w    -64.00 -39.00   0.50    0.07    --  -18.00 -54.00  39.33   50
 48  \w    -80.00 -55.00   0.50    0.07    --  -34.00 -53.00  33.74   50
 49  \w    -67.00 -37.00   0.50    0.07    --  -72.64  98.00  41.45   60
 50  \w   -111.00 -86.00   0.50    0.07    --  -72.64 -67.00  89.14   50
 51  \w   -114.00 -88.00   0.50    0.07    --  -72.64 -66.00  82.73   52
 52  \w   -113.00 -87.00   0.50    0.07    --  -72.64 -66.00  46.37   52
 53  \w   -117.00 -91.00   0.50    0.07    --  -75.17 -66.00 127.92   52
 54  \w   -110.00 -85.00   0.50    0.07    --  -72.64 -65.00 112.42   50
 55  \w   -115.00 -86.00   0.50    0.07    --  -72.64 -65.00 142.87   58
 56  \w   -111.00 -86.00   0.50    0.07    --  -75.17 -67.00 168.98   50
 57  \w   -113.00 -84.00   0.50    0.07    --  -72.64 -65.00 149.29   58
 58  \w   -111.00 -86.00   0.50    0.07    --  -72.64 -62.00 128.61   50
 59  \w   -109.00 -84.00   0.50    0.07    --  -72.64 -65.00  97.33   50
 60  \w   -115.00 -90.00   0.50    0.07    --  -72.64 -64.00  69.31   50
 61  \w   -112.00 -86.00   0.50    0.07    --  -72.64 -61.00  51.32   52
 62  \w   -109.00 -83.00   0.50    0.07    --  -70.00 -64.00  19.22   52
 63  \w   -117.00 -86.00   0.50    0.07    --  -74.00 -62.00  27.06   62
 64  \w   -112.00 -86.00   0.50    0.07    --  -72.64 -61.00  31.04   52
 65  \w   -122.00 -97.00   0.50    0.07    --  -74.00 -42.00 -32.30   50
 66  \w   -107.00 -81.00   0.50    0.07    --  -66.00 -55.00  48.42   52
 67  \w    -96.00 -70.00   0.50    0.07    --  -54.00 -54.00  84.72   52
 68  \w   -101.00 -76.00   0.50    0.07    --  -54.00 -50.00 140.25   50
 69  \w   -105.00 -79.00   0.50    0.07    --  -62.00 -55.00 103.97   52
 70  \w   -113.00 -88.00   0.50    0.07    --  -66.00 -37.00  73.64   50
 71  \w   -111.00 -86.00   0.50    0.07    --  -70.00 -20.00  93.66   50
 72  \w   -114.00 -89.00   0.50    0.07    --  -72.64 -21.00 178.60   50
 73  \w   -110.00 -85.00   0.50    0.07    --  -72.64 -19.00 -40.75   50
 74  \w   -116.00 -91.00   0.50    0.07    --  -72.64 -23.00 -77.62   50
 75  \w   -117.00 -92.00   0.50    0.07    --  -74.00 -38.00 -88.13   50
 76  \w   -113.00 -88.00   0.50    0.07    --  -70.00 -25.00-118.71   50
 77  \w   -113.00 -88.00   0.50    0.07    --  -75.17 -19.00-148.47   50
;
_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      -0.0226103000
_diffrn_orient_matrix_UB_12      -0.0699271000
_diffrn_orient_matrix_UB_13      -0.0027818000
_diffrn_orient_matrix_UB_21      0.0648375000
_diffrn_orient_matrix_UB_22      -0.0236919000
_diffrn_orient_matrix_UB_23      0.0354988000
_diffrn_orient_matrix_UB_31      -0.0132440000
_diffrn_orient_matrix_UB_32      0.0036054000
_diffrn_orient_matrix_UB_33      0.1789684000
_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  0.0454
_diffrn_reflns_av_unetI/netI     0.0240
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            15704
_diffrn_reflns_point_group_measured_fraction_full 0.968
_diffrn_reflns_point_group_measured_fraction_max 0.921
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.448
_diffrn_reflns_theta_min         5.845
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.554
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.567
_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 orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_description       block
_exptl_crystal_F_000             1616
_exptl_crystal_size_max          0.278
_exptl_crystal_size_mid          0.061
_exptl_crystal_size_min          0.038
_refine_diff_density_max         0.339
_refine_diff_density_min         -0.318
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   -0.01(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     117
_refine_ls_number_reflns         1832
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.108
_refine_ls_R_factor_all          0.0358
_refine_ls_R_factor_gt           0.0337
_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^)+(0.0636P)^2^+0.7393P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0889
_refine_ls_wR_factor_ref         0.0906
_reflns_Friedel_coverage         0.784
_reflns_Friedel_fraction_full    0.934
_reflns_Friedel_fraction_max     0.869
_reflns_number_gt                1755
_reflns_number_total             1832
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d6sc00815a2.cif
_cod_data_source_block           bm070525_1_1
_cod_depositor_comments
'Adding full bibliography for 1576860--1576861.cif.'
_cod_database_code               1576860
_shelx_shelxl_version_number     2019/3
_chemical_oxdiff_formula         C20H26N2NiO2
_shelx_estimated_absorpt_t_max   0.940
_shelx_estimated_absorpt_t_min   0.670
_diffrn_oxdiff_ac3_digest_hkl    4173f866245b97dee181af60e23d253410c010
_diffrn_oxdiff_digest_hkl
;
4359e3380b76bc2faae71fcfd52ab693f783c0
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5)
2.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C10(H10A,H10B,H10C)
;
_shelx_res_checksum              26348
_olex2_date_sample_data_collection 2025-05-12
_olex2_date_sample_submission    2025-05-12
_olex2_submission_original_sample_id bm070525_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 2.241
_oxdiff_exptl_absorpt_empirical_full_min 0.515