Chemoselective transfer hydrogenation and transfer deuteration of substituted quinolines using Hantzsch ester and D<sub>2</sub>O.
Bhatt, Tarun; Dutta, Tonmoy; Yaswanth, Kokkiripati; Kalevaru, Venkata Narayana; Wohlrab, Sebastian; Natte, Kishore; Chemical communications (Cambridge, England) 61 (2025) 12305–12308; doi:10.1039/d5cc03315b

data_7134818
_publ_section_title
;
 Chemoselective transfer hydrogenation and transfer deuteration of
 substituted quinolines using Hantzsch ester and D<sub>2</sub>O.
;
_journal_issue                   66
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              12305
_journal_page_last               12308
_journal_paper_doi               10.1039/d5cc03315b
_journal_volume                  61
_journal_year                    2025
_chemical_formula_moiety         '2(C19 H22 N2 O)'
_chemical_formula_sum            'C38 H44 N4 O2'
_chemical_formula_weight         588.77
_chemical_name_systematic        KN_TB_TFA_C1
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2025-03-02
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2025-03-05 deposited with the CCDC.	2025-07-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.6633(15)
_cell_length_b                   8.3253(8)
_cell_length_c                   21.863(2)
_cell_measurement_reflns_used    6041
_cell_measurement_temperature    298
_cell_measurement_theta_max      23.011
_cell_measurement_theta_min      2.487
_cell_volume                     3215.0(5)
_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      298
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker Apex-V Photon II'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0775
_diffrn_reflns_av_unetI/netI     0.0590
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            34030
_diffrn_reflns_point_group_measured_fraction_full 0.901
_diffrn_reflns_point_group_measured_fraction_max 0.873
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.181
_diffrn_reflns_theta_min         2.306
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.5680
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1251 before and 0.0681 after correction.
The Ratio of minimum to maximum transmission is 0.7619.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.216
_exptl_crystal_description       block
_exptl_crystal_F_000             1264
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.195
_refine_diff_density_min         -0.158
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
;
 Flack x determined using 1232 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   1.2(10)
_refine_ls_extinction_coef       0.0113(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/1 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     406
_refine_ls_number_reflns         6247
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.1097
_refine_ls_R_factor_gt           0.0475
_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^)+(0.0571P)^2^+0.3203P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1054
_refine_ls_wR_factor_ref         0.1381
_reflns_Friedel_coverage         0.705
_reflns_Friedel_fraction_full    0.796
_reflns_Friedel_fraction_max     0.742
_reflns_number_gt                3664
_reflns_number_total             6247
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc03315b2.cif
_cod_data_source_block           mo_kn_tb_tfa_c1
_cod_depositor_comments
'Adding full bibliography for 7134818--7134819.cif.'
_cod_database_code               7134818
_shelx_shelxl_version_number     2019/1
_shelx_estimated_absorpt_t_max   0.998
_shelx_estimated_absorpt_t_min   0.995
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C20(H20), C1(H1A)
2.b Secondary CH2 refined with riding coordinates:
 C35(H35A,H35B), C36(H36A,H36B), C38(H38A,H38B), C37(H37A,H37B), C21(H21A,
 H21B), C22(H22A,H22B), C19(H19A,H19B), C18(H18A,H18B), C17(H17A,H17B),
 C16(H16A,H16B), C3(H3A,H3B), C2(H2A,H2B)
2.c Aromatic/amide H refined with riding coordinates:
 C25(H25), C24(H24), C30(H30), C31(H31), C26(H26), C27(H27), C33(H33),
 C34(H34), C6(H6), C5(H5), C11(H11), C12(H12), C15(H15), C14(H14), C7(H7),
 C8(H8)
;
_shelx_res_checksum              80559
_shelx_hkl_checksum              74001
_olex2_submission_special_instructions 'No special instructions were received'