Mechanistic insights on the Lewis acid-catalyzed three-component cationic Povarov reaction: synthesis of <i>N</i>-propargyl 1,2,3,4-tetrahydroquinolines.
Rodríguez-Núñez, Yeray A; Sánchez-Márquez, Jesús; Quintero-Saumeth, Jorge; Guerra, Cristian J.; Polo-Cuadrado, Efraín; Villaman, David; Fica-Cornejo, Cristopher A; Romero Bohórquez, Arnold R; RSC advances 15 (2025) 11799–11810; doi:10.1039/d5ra01375e

data_7250662
_publ_section_title
;
 Mechanistic insights on the Lewis acid-catalyzed three-component cationic
 Povarov reaction: synthesis of <i>N</i>-propargyl
 1,2,3,4-tetrahydroquinolines.
;
_journal_issue                   15
_journal_name_full               'RSC advances'
_journal_page_first              11799
_journal_page_last               11810
_journal_paper_doi               10.1039/d5ra01375e
_journal_volume                  15
_journal_year                    2025
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C17 H20 N2 O2'
_chemical_formula_sum            'C17 H20 N2 O2'
_chemical_formula_weight         284.35
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-12-28
_audit_creation_method
;
Olex2 1.5
(compiled 2024.01.12 svn.r2f8d729c for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2025-01-08 deposited with the CCDC.	2025-04-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.2680(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.4298(3)
_cell_length_b                   17.4070(7)
_cell_length_c                   9.4334(4)
_cell_measurement_reflns_used    4550
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      26.93
_cell_measurement_theta_min      2.34
_cell_volume                     1539.18(10)
_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    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0455
_diffrn_reflns_av_unetI/netI     0.0329
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            17238
_diffrn_reflns_point_group_measured_fraction_full 0.947
_diffrn_reflns_point_group_measured_fraction_max 0.937
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.493
_diffrn_reflns_theta_min         2.340
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6970
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0966 before and 0.0548 after correction.
The Ratio of minimum to maximum transmission is 0.9348.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'light yellow'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.227
_exptl_crystal_description       block
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.226
_exptl_crystal_size_mid          0.182
_exptl_crystal_size_min          0.052
_refine_diff_density_max         0.129
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details
;
 Flack x determined using 1077 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         3314
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0546
_refine_ls_R_factor_gt           0.0440
_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^)+(0.0672P)^2^+0.1853P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1138
_refine_ls_wR_factor_ref         0.1212
_reflns_Friedel_coverage         0.878
_reflns_Friedel_fraction_full    0.899
_reflns_Friedel_fraction_max     0.879
_reflns_number_gt                2723
_reflns_number_total             3314
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ra01375e2.cif
_cod_data_source_block           dv_cf23
_cod_database_code               7250662
_shelx_shelxl_version_number     2019/1
_shelx_estimated_absorpt_t_max   0.996
_shelx_estimated_absorpt_t_min   0.982
_olex2_refinement_description
;
1.a Ternary CH refined with riding coordinates:
 C13(H13)
1.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B), C12(H12A,H12B), C15(H15A,H15B), C16(H16A,H16B),
 C17(H17A,H17B)
1.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C6(H6)
1.d Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C)
1.e :
 C11(H11)
;
_shelx_res_checksum              90946
_olex2_submission_special_instructions 'No special instructions were received'