Synthesis of Tetrahydroquinolines by Scandium-Catalyzed [3 + 3] Annulation of Anilines with Allenes and Dienes
Xu, Xian; Zheng, Xizhou; Xu, Xin; ACS Catalysis 11 (2021) 14995–15003; doi:10.1021/acscatal.1c04657

data_4519248
_publ_section_title
;
 Synthesis of Tetrahydroquinolines by Scandium-Catalyzed [3 + 3]
 Annulation of Anilines with Allenes and Dienes
;
_journal_issue                   24
_journal_name_full               'ACS Catalysis'
_journal_page_first              14995
_journal_page_last               15003
_journal_paper_doi               10.1021/acscatal.1c04657
_journal_volume                  11
_journal_year                    2021
_chemical_formula_moiety         'C24 H25 N'
_chemical_formula_sum            'C24 H25 N'
_chemical_formula_weight         327.45
_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
_audit_creation_date             2021-05-12
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_cell_angle_alpha                92.736(2)
_cell_angle_beta                 93.818(2)
_cell_angle_gamma                93.332(2)
_cell_formula_units_Z            4
_cell_length_a                   10.1618(5)
_cell_length_b                   13.2018(6)
_cell_length_c                   13.7980(6)
_cell_measurement_reflns_used    6775
_cell_measurement_temperature    120.0
_cell_measurement_theta_max      108.042
_cell_measurement_theta_min      5.592
_cell_volume                     1841.35(15)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      120.0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34138
_diffrn_reflns_av_R_equivalents  0.0776
_diffrn_reflns_av_unetI/netI     0.0516
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            54395
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.021
_diffrn_reflns_theta_min         2.796
_diffrn_source_current           3.57
_diffrn_source_power             0.2494716
_diffrn_source_voltage           69.88
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.325
_exptl_absorpt_correction_T_max  0.7506
_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 0.1026 before and 0.0724 after correction.
The Ratio of minimum to maximum transmission is 0.8467.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.181
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.204
_refine_diff_density_min         -0.295
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     468
_refine_ls_number_reflns         6775
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0920
_refine_ls_R_factor_gt           0.0555
_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^)+(0.0834P)^2^+0.2145P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1323
_refine_ls_wR_factor_ref         0.1518
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4604
_reflns_number_total             6775
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs1c04657_si_002.cif
_cod_data_source_block           ga210511i_0m
_cod_depositor_comments
;

2025-07-30
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C48 H50 N2'
_cod_original_formula_weight         654.90
_cod_original_formula_moiety         '2(C24 H25 N)'
_cod_original_formula_units_Z            2
_cod_database_code               4519248
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.909
_shelx_estimated_absorpt_t_min   0.881
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C16(H16A,H16B), C39(H39A,H39B), C40(H40A,H40B)
2.b Aromatic/amide H refined with riding coordinates:
 C35(H35), C14(H14), C34(H34), C28(H28), C38(H38), C24(H24), C11(H11),
 C44(H44), C6(H6), C4(H4), C27(H27), C30(H30), C48(H48), C22(H22), C31(H31),
 C20(H20), C3(H3), C10(H10), C23(H23), C47(H47), C7(H7), C21(H21), C45(H45),
 C46(H46)
2.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C32(H32A,H32B,H32C), C41(H41A,H41B,H41C), C8(H8A,H8B,
 H8C), C25(H25A,H25B,H25C)
;
_shelx_res_checksum              43002
_shelx_hkl_checksum              39274
_olex2_submission_special_instructions 'No special instructions were received'