Photochemical HAT-mediated site-selective C(sp<sup>3</sup>)-H aminoalkylation of cubanes catalyzed by TBADT.
Tang, Zhicheng; Liu, Mingyang; Yang, Xiuran; Zhong, Zhuang; Liu, Sensheng; Zhou, Haifeng; Chemical communications (Cambridge, England) 62 (2026) 4059–4062; doi:10.1039/d5cc07169k

data_7135382
_publ_section_title
;
 Photochemical HAT-mediated site-selective C(sp<sup>3</sup>)-H
 aminoalkylation of cubanes catalyzed by TBADT.
;
_journal_issue                   13
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              4059
_journal_page_last               4062
_journal_paper_doi               10.1039/d5cc07169k
_journal_volume                  62
_journal_year                    2026
_chemical_formula_moiety         'C H Cl3, C28 H27 N O8 S'
_chemical_formula_sum            'C29 H28 Cl3 N O8 S'
_chemical_formula_weight         656.93
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_block_doi                 10.5517/ccdc.csd.cc2qdfcy
_audit_creation_date             2025-11-06
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2025-12-09 deposited with the CCDC.	2026-01-22 downloaded from the CCDC.
;
_cell_angle_alpha                118.405(2)
_cell_angle_beta                 108.271(2)
_cell_angle_gamma                94.0150(10)
_cell_formula_units_Z            2
_cell_length_a                   10.9319(2)
_cell_length_b                   12.8338(2)
_cell_length_c                   13.0162(2)
_cell_measurement_reflns_used    15913
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      72.6240
_cell_measurement_theta_min      4.0100
_cell_volume                     1471.87(6)
_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-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      150.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 0.967
_diffrn_measured_fraction_theta_max 0.931
_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     72.00 102.00   0.50    0.05    --   62.31  15.00 150.00   60
  2  \w     60.00  90.00   0.50    0.05    --   62.31  15.00   0.00   60
  3  \w     63.00  90.00   0.50    0.05    --   62.31  15.00 -90.00   54
  4  \w     66.00  94.00   0.50    0.05    --   62.31  15.00-120.00   56
  5  \w     60.00 102.00   0.50    0.05    --   62.31  15.00-150.00   84
  6  \w     72.00 104.00   0.50    0.05    --   71.33  15.00-150.00   64
  7  \w     75.00 100.00   0.50    0.05    --   74.26  15.00 -90.00   50
  8  \w     67.00  93.00   0.50    0.05    --   74.26  15.00 -30.00   52
  9  \w     56.00  81.00   0.50    0.05    --   62.31  15.00  30.00   50
 10  \w     65.00  98.00   0.50    0.05    --   71.33  15.00  60.00   66
 11  \w     60.00 103.00   0.50    0.05    --   62.31  15.00  90.00   86
 12  \w     79.00 107.00   0.50    0.05    --   74.26  15.00 150.00   56
 13  \w     70.00 115.00   0.50    0.05    --   74.26  15.00  90.00   90
 14  \w     74.00  99.00   0.50    0.05    --   74.26  15.00 120.00   50
 15  \w     71.00  96.00   0.50    0.05    --   74.26  15.00  30.00   50
 16  \w     67.00 112.00   0.50    0.05    --   74.26  15.00   0.00   90
 17  \w     54.00 101.00   0.50    0.05    --   62.00  12.00 -44.47   94
 18  \w     78.00 103.00   0.50    0.05    --   74.26  15.00 -60.00   50
 19  \w     71.00 105.00   0.50    0.05    --   74.26  15.00-120.00   68
 20  \w     76.00 103.00   0.50    0.05    --   74.26  15.00-180.00   54
 21  \w     40.00  88.00   0.50    0.05    --   74.26-125.00 -90.00   96
 22  \w     39.00  78.00   0.50    0.05    --   62.31-125.00-120.00   78
 23  \w     25.00  63.00   0.50    0.05    --   62.31-125.00   0.00   76
 24  \w     48.00  78.00   0.50    0.05    --   62.31-125.00 -30.00   60
 25  \w     29.00  59.00   0.50    0.05    --   62.31-125.00  30.00   60
 26  \w     37.00  62.00   0.50    0.05    --   71.33-126.00  46.00   50
 27  \w     59.00  91.00   0.50    0.05    --   74.26-126.00  46.00   64
 28  \w     26.00  78.00   0.50    0.05    --   62.31-125.00 120.00  104
 29  \w     27.00  69.00   0.50    0.05    --   62.31-125.00  90.00   84
 30  \w     58.00  85.00   0.50    0.05    --   71.33-125.00  30.00   54
 31  \w     27.00  79.00   0.50    0.05    --   62.31-126.00  46.00  104
 32  \w     35.00  82.00   0.50    0.05    --   71.33-125.00 150.00   94
 33  \w     31.00  77.00   0.50    0.05    --   62.31-125.00 -60.00   92
 34  \w     52.00  87.00   0.50    0.05    --   71.33-125.00-120.00   70
 35  \w     25.00  76.00   0.50    0.05    --   62.31-125.00-180.00  102
 36  \w     54.00  80.00   0.50    0.05    --   71.33-125.00-180.00   52
 37  \w     44.00  81.00   0.50    0.05    --   71.33-125.00 -60.00   74
 38  \w     65.00  90.00   0.50    0.05    --   74.26-125.00-180.00   50
 39  \w     65.00  90.00   0.50    0.05    --   74.26-125.00 -60.00   50
 40  \w     42.00  90.00   0.50    0.05    --   74.26-125.00-150.00   96
 41  \w     43.00  90.00   0.50    0.05    --   74.26-125.00  60.00   94
 42  \w     53.00  87.00   0.50    0.05    --   71.33-125.00  90.00   68
 43  \w     39.00  90.00   0.50    0.05    --   74.26-125.00 120.00  102
 44  \w     61.00  86.00   0.50    0.05    --   74.26-125.00 150.00   50
 45  \w     64.00  89.00   0.50    0.05    --   74.26-125.00  90.00   50
 46  \w     41.00  90.00   0.50    0.05    --   74.26-125.00   0.00   98
 47  \w     53.00  90.00   0.50    0.05    --   74.26-125.00 -30.00   74
 48  \w     65.00  90.00   0.50    0.05    --   74.26-125.00-120.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix-Arc 150'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0329311000
_diffrn_orient_matrix_UB_12      0.0127939000
_diffrn_orient_matrix_UB_13      -0.1008636000
_diffrn_orient_matrix_UB_21      0.0474663000
_diffrn_orient_matrix_UB_22      0.1405093000
_diffrn_orient_matrix_UB_23      0.0904890000
_diffrn_orient_matrix_UB_31      0.1425318000
_diffrn_orient_matrix_UB_32      -0.0097090000
_diffrn_orient_matrix_UB_33      0.0556451000
_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  0.0257
_diffrn_reflns_av_unetI/netI     0.0166
_diffrn_reflns_Laue_measured_fraction_full 0.967
_diffrn_reflns_Laue_measured_fraction_max 0.931
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            19887
_diffrn_reflns_point_group_measured_fraction_full 0.967
_diffrn_reflns_point_group_measured_fraction_max 0.931
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.334
_diffrn_reflns_theta_min         4.027
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.930
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63258
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.143a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.482
_exptl_crystal_description       block
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         1.317
_refine_diff_density_min         -1.018
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     383
_refine_ls_number_reflns         5513
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0513
_refine_ls_R_factor_gt           0.0505
_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^)+(0.0776P)^2^+1.5588P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1368
_refine_ls_wR_factor_ref         0.1376
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5313
_reflns_number_total             5513
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc07169k2.cif
_cod_data_source_block           8421133_so2
_cod_original_cell_volume        1471.87(5)
_cod_database_code               7135382
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H O N S'
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C40(H40), C3(H3), C4(H4), C6(H6), C7(H7), C12(H12), C13(H13)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C23(H23), C24(H24), C26(H26), C27(H27), C33(H33), C34(H34), C36(H36),
 C37(H37)
2.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C20(H20A,H20B,H20C), C30(H30A,H30B,H30C), C38(H38A,H38B,
 H38C)
;
_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 1.397
_oxdiff_exptl_absorpt_empirical_full_min 0.660