Convenient lanthanum-mediated synthesis of bulky <i>tert</i>-alkyl amines from nitriles.
Burke, Emily K.; Robertson, Katherine N.; Speed, Alexander W. H.; Chemical communications (Cambridge, England) 61 (2025) 1172–1175; doi:10.1039/d4cc05831c

data_7134055
_publ_section_title
;
 Convenient lanthanum-mediated synthesis of bulky <i>tert</i>-alkyl amines
 from nitriles.
;
_journal_issue                   6
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              1172
_journal_page_last               1175
_journal_paper_doi               10.1039/d4cc05831c
_journal_volume                  61
_journal_year                    2025
_chemical_formula_moiety         'C14 H21 F3 N, 0.5(O4 S), H2 O'
_chemical_formula_sum            'C14 H23 F3 N O3 S0.5'
_chemical_formula_weight         326.36
_space_group_crystal_system      orthorhombic
_space_group_IT_number           36
_space_group_name_Hall           'C 2c -2'
_space_group_name_H-M_alt        'C m c 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_method           SHELXL-2019/3
_audit_update_record
;
2024-10-28 deposited with the CCDC.	2024-12-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   29.6157(17)
_cell_length_b                   8.9695(5)
_cell_length_c                   12.2342(7)
_cell_measurement_reflns_used    9976
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      74.4819
_cell_measurement_theta_min      5.9766
_cell_volume                     3249.9(3)
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_collection       'Bruker Instrument Service v8.5.0.11 RC8'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2015)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 '100 \\times 140 mm^2^ CMOS sensor'
_diffrn_detector_area_resol_mean 7.3910
_diffrn_detector_type            'Bruker PHOTON III'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       '\k--geometry diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0366
_diffrn_reflns_av_unetI/netI     0.0324
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            17526
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.571
_diffrn_reflns_theta_min         5.152
_diffrn_source_current           1.1
_diffrn_source_power             0.06
_diffrn_source_type              'Incoatec I\mS 3.0'
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    1.560
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_correction_T_min  0.6610
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
J. Appl. Cryst. 48, 3-10.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_description       'flat rod'
_exptl_crystal_F_000             1384
_exptl_crystal_size_max          0.157
_exptl_crystal_size_mid          0.047
_exptl_crystal_size_min          0.024
_refine_diff_density_max         0.144
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.11(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         3303
_refine_ls_number_restraints     42
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0289
_refine_ls_R_factor_gt           0.0275
_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^)+(0.0335P)^2^+1.0236P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0691
_refine_ls_wR_factor_ref         0.0704
_reflns_Friedel_coverage         0.861
_reflns_Friedel_fraction_full    0.960
_reflns_Friedel_fraction_max     0.951
_reflns_number_gt                3199
_reflns_number_total             3303
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc05831c2.cif
_cod_data_source_block           AS048C_polymorph2_minor
_cod_depositor_comments
'Adding full bibliography for 7134054--7134055.cif.'
_cod_original_formula_sum        'C14 H23 F3 N O3 S0.50'
_cod_database_code               7134055
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_min   0.792
_shelx_estimated_absorpt_t_max   0.964
_diffrn_source_source            'microfocus sealed tube'
_shelx_res_checksum              49059
_shelx_hkl_checksum              65373