Electron donor-acceptor complex offers a diverse approach for carbonyl alkylative amination.
Paul, Hrishikesh; Chakraborty, Arijit; Mandal, Animesh; Das, Dibyangshu; Mahapatra, Sanat Kumar; Roy, Lisa; Chatterjee, Indranil; Chemical science 16 (2025) 20061–20072; doi:10.1039/d5sc04087f

data_1575874
_publ_section_title
;
 Electron donor-acceptor complex offers a diverse approach for carbonyl
 alkylative amination.
;
_journal_issue                   42
_journal_name_full               'Chemical science'
_journal_page_first              20061
_journal_page_last               20072
_journal_paper_doi               10.1039/d5sc04087f
_journal_volume                  16
_journal_year                    2025
_chemical_formula_moiety         'C20 H25 N O2'
_chemical_formula_sum            'C20 H25 N O2'
_chemical_formula_weight         311.41
_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     direct
_audit_creation_date             2024-12-13
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-12-13 deposited with the CCDC.	2025-09-19 downloaded from the CCDC.
;
_cell_angle_alpha                96.969(4)
_cell_angle_beta                 99.160(4)
_cell_angle_gamma                106.540(4)
_cell_formula_units_Z            2
_cell_length_a                   7.8403(11)
_cell_length_b                   10.3493(13)
_cell_length_c                   11.6156(16)
_cell_measurement_reflns_used    9991
_cell_measurement_temperature    298
_cell_measurement_theta_max      28.247
_cell_measurement_theta_min      3.600
_cell_volume                     878.0(2)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-1997  (Sheldrick, 2008)'
_diffrn_ambient_temperature      298
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX2 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  0.0497
_diffrn_reflns_av_unetI/netI     0.0269
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_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            28905
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.384
_diffrn_reflns_theta_min         2.085
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6355
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1461 before and 0.0667 after correction.
The Ratio of minimum to maximum transmission is 0.8522.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.178
_exptl_crystal_description       block
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.231
_exptl_crystal_size_mid          0.156
_exptl_crystal_size_min          0.123
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.031
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         4365
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.094
_refine_ls_R_factor_all          0.0604
_refine_ls_R_factor_gt           0.0550
_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^)+(0.0514P)^2^+0.2613P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1389
_refine_ls_wR_factor_ref         0.1427
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3905
_reflns_number_total             4365
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc04087f2.cif
_cod_data_source_block           icar_574_p_0m_a
_cod_depositor_comments          'Adding full bibliography for 1575874.cif.'
_cod_database_code               1575874
_shelx_shelxl_version_number     2019/1
_shelx_estimated_absorpt_t_max   0.991
_shelx_estimated_absorpt_t_min   0.983
_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.a Ternary CH refined with riding coordinates:
 C16(H16)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C15(H15), C14(H14), C13(H13), C4(H4), C12(H12), C11(H11)
2.c Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C), C8(H8A,H8B,H8C), C18(H18A,H18B,H18C), C17(H17A,H17B,H17C),
 C20(H20A,H20B,H20C)
;
_shelx_res_checksum              97925
_olex2_submission_special_instructions 'No special instructions were received'