Direct preparation of unprotected aminimides (R<sub>3</sub>N<sup>+</sup>-NH<sup>-</sup>) from natural aliphatic tertiary alkaloids (R<sub>3</sub>N) by [Mn(TDCPP)Cl]-catalysed N-amination reaction.
Zhang, Shilong; Liu, Yungen; Xing, Fangrong; Che, Chi-Ming; Chemical communications (Cambridge, England) 56 (2020) 9102–9105; doi:10.1039/d0cc02934c

data_7126864
_publ_section_title
;
 Direct preparation of unprotected aminimides
 (R<sub>3</sub>N<sup>+</sup>-NH<sup>-</sup>) from natural aliphatic
 tertiary alkaloids (R<sub>3</sub>N) by [Mn(TDCPP)Cl]-catalysed
 N-amination reaction.
;
_journal_issue                   64
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              9102
_journal_page_last               9105
_journal_paper_doi               10.1039/d0cc02934c
_journal_volume                  56
_journal_year                    2020
_chemical_formula_moiety         '0.5(C116 H72 Cl16 Mn2 N10)'
_chemical_formula_sum            'C58 H36 Cl8 Mn N5'
_chemical_formula_weight         1141.46
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc2444l1
_audit_creation_date             2019-11-01
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-12-05 deposited with the CCDC.	2020-07-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.6724(19)
_cell_length_b                   19.811(3)
_cell_length_c                   20.784(3)
_cell_measurement_reflns_used    9717
_cell_measurement_temperature    100
_cell_measurement_theta_max      28.48
_cell_measurement_theta_min      2.28
_cell_volume                     5217.9(13)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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_temperature      100
_diffrn_detector                 'Bruker PHOTON 100 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'BrukerD8 venture microsource'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0684
_diffrn_reflns_av_unetI/netI     0.0321
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            70468
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.527
_diffrn_reflns_theta_min         2.145
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.708
_exptl_absorpt_correction_T_max  0.7272
_exptl_absorpt_correction_T_min  0.6461
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1423 before and 0.0994 after correction. The Ratio of minimum to maximum transmission is 0.8885. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            'dark red'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.453
_exptl_crystal_description       plate
_exptl_crystal_F_000             2320
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.826
_refine_diff_density_min         -0.710
_refine_diff_density_rms         0.136
_refine_ls_extinction_coef       0.0031(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.362
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     341
_refine_ls_number_reflns         6616
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.362
_refine_ls_R_factor_all          0.1039
_refine_ls_R_factor_gt           0.1003
_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^)+47.7934P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2313
_refine_ls_wR_factor_ref         0.2327
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6238
_reflns_number_total             6616
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc02934c2.cif
_cod_data_source_block           zsl-NMnTDCPP
_cod_depositor_comments
'Adding full bibliography for 7126862--7126864.cif.'
_cod_database_code               7126864
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.972
_shelx_estimated_absorpt_t_min   0.728
_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. Uiso/Uaniso restraints and constraints
Uanis(C29) = Uanis(C29A)
3. Others
 Sof(H28)=Sof(C29A)=Sof(H29D)=Sof(H29E)=Sof(H29F)=1-FVAR(1)
 Sof(H24)=Sof(C29)=Sof(H29A)=Sof(H29B)=Sof(H29C)=FVAR(1)
 Fixed Sof: Mn1(0.5) N3(0.5)
4.a Aromatic/amide H refined with riding coordinates:
 C15(H15), C14(H14), C22(H22), C7(H7), C10(H10), C18(H18), C12(H12), C20(H20),
 C19(H19), C11(H11), C23(H23), C24(H24), C25(H25), C27(H27), C28(H28), C26(H26)
4.b Idealised Me refined as rotating group:
 C29(H29A,H29B,H29C), C29A(H29D,H29E,H29F)
;
_olex2_submission_special_instructions 'No special instructions were received'