Cobalt-catalyzed amination of aziridines and azetidines toward 1,2- and 1,3-diamines.
Cheng, Ling-Chao; Wang, Zhihua; He, Xinglei; Liang, Wangfu; Ye, Ke-Yin; Organic & biomolecular chemistry 22 (2024) 2554–2557; doi:10.1039/d4ob00168k

data_7159827
_publ_section_title
;
 Cobalt-catalyzed amination of aziridines and azetidines toward 1,2- and
 1,3-diamines.
;
_journal_issue                   13
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2554
_journal_page_last               2557
_journal_paper_doi               10.1039/d4ob00168k
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C28 H28 N2 O6 S3'
_chemical_formula_sum            'C28 H28 N2 O6 S3'
_chemical_formula_weight         584.70
_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     dual
_audit_creation_date             2023-12-14
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2023-12-29 deposited with the CCDC.	2024-03-01 downloaded from the CCDC.
;
_cell_angle_alpha                76.184(3)
_cell_angle_beta                 78.526(2)
_cell_angle_gamma                74.084(2)
_cell_formula_units_Z            2
_cell_length_a                   9.9841(2)
_cell_length_b                   9.9889(2)
_cell_length_c                   15.0529(5)
_cell_measurement_reflns_used    9415
_cell_measurement_temperature    292.98(16)
_cell_measurement_theta_max      76.0590
_cell_measurement_theta_min      3.0470
_cell_volume                     1387.52(6)
_computing_cell_refinement       'CrysAlisPro 1.171.43.98a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.43.98a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.43.98a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      292.98(16)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.947
_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     62.00  87.00   0.50    0.06    --   46.11 165.00  15.00   50
  2  \w     80.00 105.00   0.50    0.25    --  105.07 165.00  15.00   50
  3  \w    102.00 127.00   0.50    0.25    --  105.07 116.00-131.00   50
  4  \w     96.00 168.00   0.50    0.25    --  105.07 125.00-180.00  144
  5  \w     93.00 175.00   0.50    0.25    --  105.07  45.00 150.00  164
  6  \w     28.00 118.00   0.50    0.06    --   46.11  77.00 -60.00  180
  7  \w    -12.00  14.00   0.50    0.06    --  -46.11  19.00  60.00   52
  8  \w    -11.00  17.00   0.50    0.06    --  -46.11  19.00 150.00   56
  9  \w    -67.00 -31.00   0.50    0.25    -- -104.50  61.00  90.00   72
 10  \w    -62.00 -32.00   0.50    0.25    -- -104.50  61.00 -90.00   60
 11  \w    -62.00 -31.00   0.50    0.25    -- -104.50  61.00-120.00   62
 12  \w    -63.00 -31.00   0.50    0.25    -- -104.50  61.00-150.00   64
 13  \w    -19.00  24.00   0.50    0.06    --  -46.11  19.00-180.00   86
 14  \w    -85.00  -7.00   0.50    0.06    --  -46.11 116.00-131.00  156
 15  \w   -101.00 -76.00   0.50    0.06    --  -46.11 165.00  15.00   50
 16  \w   -122.00 -71.00   0.50    0.25    -- -104.50 165.00  15.00  102
 17  \w   -111.00 -47.00   0.50    0.25    -- -104.50 125.00   0.00  128
 18  \w   -111.00 -59.00   0.50    0.25    -- -104.50 125.00 -60.00  104
 19  \w   -109.00 -63.00   0.50    0.25    -- -104.50 116.00-131.00   92
 20  \w    -29.00  28.00   0.50    0.06    --   46.11 -19.00 150.00  114
 21  \w     41.00 107.00   0.50    0.25    --  105.07 -77.00 150.00  132
 22  \w    -15.00  30.00   0.50    0.06    --   46.11 -19.00   0.00   90
 23  \w     35.00 107.00   0.50    0.25    --  105.07 -77.00 -60.00  144
 24  \w     36.00 103.00   0.50    0.25    --  105.07 -95.00 -60.00  134
 25  \w     40.00 136.00   0.50    0.25    --  105.07-165.00  -6.00  192
 26  \w     63.00 103.00   0.50    0.25    --  105.07 -95.00  30.00   80
 27  \w     37.00  75.00   0.50    0.25    --  105.07-116.00 140.00   76
 28  \w     79.00 107.00   0.50    0.25    --  105.07-116.00 140.00   56
 29  \w     71.00  96.00   0.50    0.25    --  105.07 -95.00 150.00   50
 30  \w     32.00  66.00   0.50    0.25    --  105.07 -95.00 150.00   68
 31  \w     36.00  62.00   0.50    0.06    --   46.11-116.00 140.00   52
 32  \w     76.00 111.00   0.50    0.06    --   46.11-165.00  -6.00   70
 33  \w     43.00  73.00   0.50    0.06    --   46.11-165.00  -6.00   60
 34  \w   -125.00-100.00   0.50    0.25    -- -104.50-165.00  -6.00   50
 35  \w   -134.00 -80.00   0.50    0.25    -- -104.50-116.00 140.00  108
 36  \w   -115.00 -50.00   0.50    0.06    --  -46.11-165.00  -6.00  130
 37  \w   -171.00-127.00   0.50    0.25    -- -104.50 -45.00-120.00   88
 38  \w   -169.00-143.00   0.50    0.25    -- -104.50 -15.00-150.00   52
 39  \w   -127.00 -90.00   0.50    0.25    -- -104.50 -15.00-150.00   74
 40  \w   -119.00 -91.00   0.50    0.25    -- -104.50 -45.00   0.00   56
 41  \w   -174.00 -90.00   0.50    0.25    -- -104.50 -45.00 -30.00  168
 42  \w   -173.00-144.00   0.50    0.25    -- -104.50 -45.00   0.00   58
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0129608000
_diffrn_orient_matrix_UB_12      0.0587116000
_diffrn_orient_matrix_UB_13      -0.1049293000
_diffrn_orient_matrix_UB_21      0.1608420000
_diffrn_orient_matrix_UB_22      -0.0577051000
_diffrn_orient_matrix_UB_23      -0.0084390000
_diffrn_orient_matrix_UB_31      -0.0156020000
_diffrn_orient_matrix_UB_32      -0.1412998000
_diffrn_orient_matrix_UB_33      -0.0160576000
_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  0.0289
_diffrn_reflns_av_unetI/netI     0.0314
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.947
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            17490
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.947
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.237
_diffrn_reflns_theta_min         3.055
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.827
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88812
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.98a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_description       block
_exptl_crystal_F_000             612
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.508
_refine_diff_density_min         -0.347
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     353
_refine_ls_number_reflns         5497
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.0746
_refine_ls_R_factor_gt           0.0685
_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^)+(0.0726P)^2^+3.3505P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2097
_refine_ls_wR_factor_ref         0.2129
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4746
_reflns_number_total             5497
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob00168k2.cif
_cod_data_source_block           cjc
_cod_depositor_comments
'Adding full bibliography for 7159826--7159827.cif.'
_cod_original_cell_volume        1387.52(7)
_cod_database_code               7159827
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.872
_shelx_estimated_absorpt_t_min   0.765
_reflns_odcompleteness_completeness 99.98
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,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:
 C00E(H00E)
2.b Secondary CH2 refined with riding coordinates:
 C00F(H00A,H00C), C00P(H00D,H00F)
2.c Aromatic/amide H refined with riding coordinates:
 N00B(H00B), C00I(H00I), C00J(H00J), C00K(H00K), C16(H16), C00N(H00N),
 C00O(H00O), C00Q(H00Q), C00R(H00R), C00S(H00S), C00T(H00T), C00U(H00U),
 C00V(H00V), C00W(H00W), C00X(H00X), C00Y(H00Y), C00Z(H00Z), C010(H010),
 C011(H011), C012(H012)
2.d Idealised Me refined as rotating group:
 C013(H01A,H01B,H01C)
;
_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 1.192
_oxdiff_exptl_absorpt_empirical_full_min 0.868