Triple role of boronic acid as a catalyst in the alkylation of quinoline to functionalized tetrahydroquinoline.
Senapati, Siddhartha Kumar; Borah, Asish; Hazarika, Swagata; Das, Animesh; Organic & biomolecular chemistry 23 (2025) 7275–7282; doi:10.1039/d5ob00895f

data_7160606
_publ_section_title
;
 Triple role of boronic acid as a catalyst in the alkylation of quinoline
 to functionalized tetrahydroquinoline.
;
_journal_issue                   31
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              7275
_journal_page_last               7282
_journal_paper_doi               10.1039/d5ob00895f
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C38 H45 N O2'
_chemical_formula_sum            'C38 H45 N O2'
_chemical_formula_weight         547.75
_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     iterative
_audit_creation_date             2025-03-17
_audit_creation_method
;
Olex2 1.5-alpha
(compiled 2023.11.24 svn.r209d9fb2 for OlexSys, GUI svn.r6869)
;
_audit_update_record
;
2025-03-21 deposited with the CCDC.	2025-06-24 downloaded from the CCDC.
;
_cell_angle_alpha                68.406(6)
_cell_angle_beta                 85.378(7)
_cell_angle_gamma                66.181(6)
_cell_formula_units_Z            2
_cell_length_a                   11.629(3)
_cell_length_b                   12.102(3)
_cell_length_c                   13.779(3)
_cell_measurement_reflns_used    9947
_cell_measurement_temperature    296.00
_cell_measurement_theta_max      26.37
_cell_measurement_theta_min      2.40
_cell_volume                     1644.2(7)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5-alpha (Bourhis et al., 2015)'
_diffrn_ambient_temperature      296.00
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_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  0.0367
_diffrn_reflns_av_unetI/netI     0.0214
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            48983
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.374
_diffrn_reflns_theta_min         2.129
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.067
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6798
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1440 before and 0.0550 after correction.
The Ratio of minimum to maximum transmission is 0.9120.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'dark red'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.106
_exptl_crystal_description       block
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.31
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.333
_refine_diff_density_rms         0.031
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     387
_refine_ls_number_reflns         6662
_refine_ls_number_restraints     23
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0706
_refine_ls_R_factor_gt           0.0543
_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^)+(0.0688P)^2^+0.4850P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1392
_refine_ls_wR_factor_ref         0.1583
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5260
_reflns_number_total             6662
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob00895f2.cif
_cod_data_source_block           sk_381_0m_a
_cod_depositor_comments          'Adding full bibliography for 7160606.cif.'
_cod_original_cell_volume        1644.1(7)
_cod_database_code               7160606
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, H14b of C14, H4 of C4, H6 of C6, H16 of C16, H3 of C3,
  H13 of C13, H15 of C15, H17 of C17, H18 of C18, H20 of C20, H21 of C21, H22
  of C22, H23 of C23, H24 of C24, H30 of C30, H26 of C26, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, H14a of C14, All O(H) groups
2. Restrained distances
 C9-C10 \\sim C9-C10A
 with sigma of 0.02
 C10-C12 \\sim C10A-C12
 with sigma of 0.04
 C10-C5 \\sim C10A-C5A
 with sigma of 0.02
 C9-C5 \\sim C9-C5A
 with sigma of 0.04
 C5-C12 \\sim C5A-C12
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C10A) = Uanis(C10)
4. Rigid body (RIGU) restrains
 C12, C5, C5A, C10, C10A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(H12c)=Sof(H12d)=Sof(C5A)=Sof(H5Aa)=Sof(H5Ab)=Sof(C10A)=Sof(H10c)=
 Sof(H10d)=1-FVAR(1)
 Sof(C10)=Sof(H10a)=Sof(H10b)=Sof(C5)=Sof(H5a)=Sof(H5b)=Sof(H12a)=Sof(H12b)=
 FVAR(1)
6.a Ternary CH refined with riding coordinates:
 C18(H18)
6.b Secondary CH2 refined with riding coordinates:
 C7(H7a,H7b), C10(H10a,H10b), C5(H5a,H5b), C12(H12a,H12b), C12(H12c,H12d),
 C5A(H5Aa,H5Ab), C10A(H10c,H10d)
6.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C13(H13), C3(H3), C4(H4), C15(H15), C16(H16), C17(H17), C20(H20),
 C21(H21), C22(H22), C23(H23), C24(H24), C26(H26), C30(H30)
6.d Fitted hexagon refined as free rotating group:
 C11(C6,C1,C13,C3,C4)
6.e Tetrahedral OH refined with riding coordinates:
 O1(H1)
6.f Idealised Me refined as rotating group:
 C32(H32a,H32b,H32c), C34(H34a,H34b,H34c), C35(H35a,H35b,H35c), C36(H36a,H36b,
 H36c), C37(H37a,H37b,H37c), C38(H38a,H38b,H38c)
;
_shelx_res_checksum              62053
_olex2_submission_special_instructions 'No special instructions were received'