Regioselective side-chain amination of 2-alkyl azacycles by radical translocation: total synthesis of tetraponerine T8.
Griggs, Samuel D.; Martin-Roncero, Alejandro; Nelson, Adam; Marsden, Stephen P.; Chemical communications (Cambridge, England) 57 (2021) 919–922; doi:10.1039/d0cc07625b

data_7127654
_publ_section_title
;
 Regioselective side-chain amination of 2-alkyl azacycles by radical
 translocation: total synthesis of tetraponerine T8.
;
_journal_issue                   7
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              919
_journal_page_last               922
_journal_paper_doi               10.1039/d0cc07625b
_journal_volume                  57
_journal_year                    2021
_chemical_formula_moiety         'C13 H18 N2 O2 S'
_chemical_formula_sum            'C13 H18 N2 O2 S'
_chemical_formula_weight         266.35
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-02-18
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-11-19 deposited with the CCDC.	2020-12-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 108.771(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.2920(2)
_cell_length_b                   13.7654(2)
_cell_length_c                   9.3825(2)
_cell_measurement_reflns_used    4732
_cell_measurement_temperature    125.01(10)
_cell_measurement_theta_max      73.4140
_cell_measurement_theta_min      4.5250
_cell_volume                     1258.55(4)
_computing_cell_refinement       'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      125.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3095
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.988
_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   -116.00 -17.00   1.00    1.00    --  -41.04 -37.00   0.00   99
  2  \w    -99.00 -18.00   1.00    1.00    --  -41.04 -57.00 -90.00   81
  3  \w   -106.00 -26.00   1.00    1.00    --  -41.04 -37.00-180.00   80
  4  \w    -32.00   1.00   1.00    1.00    --   41.04 -37.00-180.00   33
  5  \w     33.00  61.00   1.00    1.00    --   41.04 -37.00 -90.00   28
  6  \w      5.00  52.00   1.00    1.00    --   41.04 -37.00-180.00   47
  7  \w     82.00 121.00   1.00    3.00    --  106.02  45.00 120.00   39
  8  \w     78.00 171.00   1.00    3.00    --  106.02  61.00 -60.00   93
  9  \w     92.00 175.00   1.00    3.00    --  106.02  61.00  60.00   83
 10  \w     45.00 128.00   1.00    3.00    --  106.02 -30.00 120.00   83
 11  \w    143.00 175.00   1.00    3.00    --  106.02  45.00 150.00   32
 12  \w     97.00 159.00   1.00    3.00    --  106.02  45.00-150.00   62
 13  \w     80.00 106.00   1.00    3.00    --  106.02  45.00-180.00   26
 14  \w    143.00 168.00   1.00    3.00    --  106.02  45.00-180.00   25
 15  \w     82.00 108.00   1.00    3.00    --  106.02  45.00 -30.00   26
 16  \w     87.00 140.00   1.00    3.00    --  106.02  45.00  30.00   53
 17  \w    125.00 176.00   1.00    3.00    --  106.02  45.00 120.00   51
 18  \w     82.00 108.00   1.00    3.00    --  106.02  45.00 150.00   26
 19  \w     35.00 126.00   1.00    3.00    --  106.02 -61.00 -60.00   91
 20  \w     77.00 114.00   1.00    3.00    --  106.02  61.00-180.00   37
 21  \w     81.00 137.00   1.00    3.00    --  106.02  45.00   0.00   56
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0673049000
_diffrn_orient_matrix_UB_12      -0.0866309000
_diffrn_orient_matrix_UB_13      0.1008272000
_diffrn_orient_matrix_UB_21      0.1180064000
_diffrn_orient_matrix_UB_22      0.0007073000
_diffrn_orient_matrix_UB_23      -0.0677037000
_diffrn_orient_matrix_UB_31      0.0808987000
_diffrn_orient_matrix_UB_32      0.0707807000
_diffrn_orient_matrix_UB_33      0.1238227000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0366
_diffrn_reflns_av_unetI/netI     0.0304
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            8794
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.464
_diffrn_reflns_theta_min         4.538
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.258
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.771
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.43c (Rigaku Oxford Diffraction, 2018)
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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.406
_exptl_crystal_description       plate
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.323
_refine_diff_density_min         -0.434
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         2504
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0374
_refine_ls_R_factor_gt           0.0328
_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^)+(0.0398P)^2^+0.5473P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0804
_refine_ls_wR_factor_ref         0.0842
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2258
_reflns_number_total             2504
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc07625b2.cif
_cod_data_source_block           sg_2_39_a
_cod_depositor_comments
'Adding full bibliography for 7127654--7127656.cif.'
_cod_database_code               7127654
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C52  H72  N8  O8  S4  '
_reflns_odcompleteness_completeness 99.96
_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
2.a Ternary CH refined with riding coordinates:
 C7(H7), C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C10(H10A,H10B), C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1A), C2(H2), C3(H3), C4(H4), C5(H5)
;
_olex2_date_sample_data_collection 2019-02-14
_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 1.154
_oxdiff_exptl_absorpt_empirical_full_min 0.895