TiF<sub>4</sub>-mediated, one-pot, reductive amination of carboxylic acids with borane-ammonia.
Snyder, Madison J.; Alawaed, Abdulkhaliq A.; Li, Chunge; Pacentine, Samantha; Hamann, Henry J.; Ramachandran, P. Veeraraghavan; RSC advances 14 (2024) 31205–31209; doi:10.1039/d4ra05888g

data_7249415
_publ_section_title
;
 TiF<sub>4</sub>-mediated, one-pot, reductive amination of carboxylic
 acids with borane-ammonia.
;
_journal_issue                   42
_journal_name_full               'RSC advances'
_journal_page_first              31205
_journal_page_last               31209
_journal_paper_doi               10.1039/d4ra05888g
_journal_volume                  14
_journal_year                    2024
_chemical_formula_sum            'C14 H24 B N'
_chemical_formula_weight         217.15
_chemical_name_systematic        Borane-N-benzyl-1-cyclohexylmethanamine
_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   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2019/3
_audit_update_record
;
2024-07-26 deposited with the CCDC.	2024-09-24 downloaded from the CCDC.
;
_cell_angle_alpha                68.308(10)
_cell_angle_beta                 71.722(13)
_cell_angle_gamma                79.828(13)
_cell_formula_units_Z            2
_cell_length_a                   8.552(2)
_cell_length_b                   9.056(4)
_cell_length_c                   9.909(3)
_cell_measurement_reflns_used    9951
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      32.6894
_cell_measurement_theta_min      2.4263
_cell_volume                     675.5(4)
_computing_cell_refinement       'SAINT V8.40B (Bruker, 2020)'
_computing_data_collection       'Apex4 v2022.10-1 (Bruker, 2022)'
_computing_data_reduction        'SAINT V8.40B (Bruker, 2020)'
_computing_structure_refinement
;  
SHELXL-2019/2 (Sheldrick, 2015a, 2019), 
SHELXLE Rev1573 (H\"ubschle et al., 2011)
;
_computing_structure_solution    'SHELXT (Sheldrick, 2015b)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 7.4074
_diffrn_detector_type
'PhotonII charge-integrating pixel array (CPAD)'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'three circle diffractometer'
_diffrn_measurement_device_type  'Bruker AXS D8 Quest'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_monochromator  'Triumph curved graphite crystal'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0466
_diffrn_reflns_av_unetI/netI     0.0270
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            42471
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.272
_diffrn_reflns_theta_min         2.298
_diffrn_source                   'fine focus sealed tube X-ray source'
_diffrn_source_current           '30 mA'
_diffrn_source_voltage           '50 kV'
_exptl_absorpt_coefficient_mu    0.060
_exptl_absorpt_correction_T_max  0.7465
_exptl_absorpt_correction_T_min  0.6864
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS 2016/2: 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    1.068
_exptl_crystal_description       plate
_exptl_crystal_F_000             240
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Hexanes'
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.090
_refine_diff_density_max         0.291
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     150
_refine_ls_number_reflns         5179
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0698
_refine_ls_R_factor_gt           0.0467
_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^)+(0.0586P)^2^+0.1274P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1199
_refine_ls_wR_factor_ref         0.1336
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3780
_reflns_number_total             5179
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ra05888g2.cif
_cod_data_source_block           Madison02_a
_cod_database_code               7249415
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_min   0.983
_shelx_estimated_absorpt_t_max   0.995
_shelx_res_checksum              38385
_shelx_hkl_checksum              99307