Borane-catalyzed cascade Friedel–Crafts alkylation/[1,5]-hydride transfer/Mannich cyclization to afford tetrahydroquinolines
Zhang, Bei-Bei; Peng, Shuo; Wang, Feiyi; Lu, Cuifen; Nie, Junqi; Chen, Zuxing; Yang, Guichun; Ma, Chao; Chemical Science 13 (2022) 775–780; doi:10.1039/D1SC05629H

data_1565906
_publ_section_title
;
 Borane-catalyzed cascade Friedel--Crafts alkylation/[1,5]-hydride
 transfer/Mannich cyclization to afford tetrahydroquinolines
;
_journal_issue                   3
_journal_name_full               'Chemical Science'
_journal_page_first              775
_journal_page_last               780
_journal_paper_doi               10.1039/D1SC05629H
_journal_volume                  13
_journal_year                    2022
_chemical_formula_moiety         'C24 H29 N O3'
_chemical_formula_sum            'C24 H29 N O3'
_chemical_formula_weight         379.48
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-07-28
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_audit_update_record
;
2021-10-06 deposited with the CCDC.	2021-12-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.2320(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   32.9756(4)
_cell_length_b                   9.21260(10)
_cell_length_c                   13.7861(2)
_cell_measurement_reflns_used    7525
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      74.1820
_cell_measurement_theta_min      2.7240
_cell_volume                     4107.88(9)
_computing_cell_refinement       'CrysAlisPro 1.171.39.34b (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.34b (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.34b (Rigaku OD, 2017)'
_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 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.946
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w     -6.00  66.00   0.50    0.92    --   39.95 -57.00  60.00  144
  2  \w     48.00 114.00   0.50    0.92    --   39.95  57.00  30.00  132
  3  \w    104.00 173.00   0.50    3.68    --  111.37 102.00 -60.00  138
  4  \w     93.00 168.00   0.50    3.68    --  111.37 125.00-120.00  150
  5  \w     64.00  90.00   0.50    0.92    --   39.95  57.00-150.00   52
  6  \w     17.00  49.00   0.50    0.92    --   39.95  57.00-150.00   64
  7  \w     80.00 108.00   0.50    3.68    --  111.37 -94.00 -60.00   56
  8  \w     69.00 111.00   0.50    3.68    --  111.37-102.00-163.00   84
  9  \w     55.00  81.00   0.50    0.92    --   39.95-102.00-163.00   52
 10  \w      6.00  31.00   0.50    0.92    --   39.95-102.00-163.00   50
 11  \w     35.00 116.00   0.50    3.68    --  111.37-125.00  60.00  162
 12  \w     73.00 107.00   0.50    3.68    --  111.37 -94.00  90.00   68
 13  \w     75.00 116.00   0.50    3.68    --  111.37-125.00  90.00   82
 14  \w     39.00  68.00   0.50    3.68    --  111.37 -94.00  90.00   58
 15  \w    -70.00  17.00   0.50    0.92    --  -39.95 102.00 -60.00  174
 16  \w    -72.00 -19.00   0.50    3.68    --  -94.50 125.00   0.00  106
 17  \w    -83.00 -38.00   0.50    3.68    --  -94.50 102.00 -60.00   90
 18  \w    -98.00 -73.00   0.50    3.68    --  -94.50 -61.00-150.00   50
 19  \w   -126.00 -81.00   0.50    3.68    --  -94.50 -94.00-150.00   90
 20  \w   -141.00-104.00   0.50    3.68    --  -94.50-102.00-163.00   74
 21  \w   -158.00-132.00   0.50    3.68    --  -94.50 -94.00-150.00   52
 22  \w   -154.00 -70.00   0.50    3.68    --  -94.50-125.00 -30.00  168
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0065624000
_diffrn_orient_matrix_UB_12      -0.0602155000
_diffrn_orient_matrix_UB_13      0.1061786000
_diffrn_orient_matrix_UB_21      -0.0169510000
_diffrn_orient_matrix_UB_22      -0.1483597000
_diffrn_orient_matrix_UB_23      -0.0406247000
_diffrn_orient_matrix_UB_31      0.0440222000
_diffrn_orient_matrix_UB_32      -0.0482599000
_diffrn_orient_matrix_UB_33      -0.0074800000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0196
_diffrn_reflns_av_unetI/netI     0.0201
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.946
_diffrn_reflns_limit_h_max       40
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            11622
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.946
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.011
_diffrn_reflns_theta_min         2.732
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.635
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57317
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.34b (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.227
_exptl_crystal_description       needle
_exptl_crystal_F_000             1632
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     258
_refine_ls_number_reflns         4002
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0365
_refine_ls_R_factor_gt           0.0335
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0396P)^2^+3.4593P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0852
_refine_ls_wR_factor_ref         0.0884
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3698
_reflns_number_total             4002
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc05629h2.cif
_cod_data_source_block           machao-zhangbeibei-727
_cod_depositor_comments
'Adding full bibliography for 1565906--1565907.cif.'
_cod_database_code               1565906
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H O N'
_shelx_estimated_absorpt_t_max   0.981
_shelx_estimated_absorpt_t_min   0.969
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 Ternary CH refined with riding coordinates:
 C18(H18), C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C19(H19A,H19B), C23(H23A,H23B)
2.c Aromatic/amide H refined with riding coordinates:
 C17(H17), C10(H10), C13(H13), C16(H16), C14(H14), C15(H15), C6(H6), C7(H7)
2.d Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C2(H2A,H2B,H2C), C3(H3A,H3B,H3C), C24(H24A,H24B,H24C),
 C4(H4A,H4B,H4C)
;
_shelx_res_checksum              52048
_shelx_hkl_checksum              30269
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.022
_oxdiff_exptl_absorpt_empirical_full_min 0.709