Multistep synthesis of cationic lipid-like compounds based on a difluorotetrahydropyridine scaffold as amphiphilic nanocarriers.
Kaukulis, Martins; Rucins, Martins; Muhamadejevs, Ruslans; Mishnev, Anatoly; Pajuste, Karlis; Plotniece, Aiva; Sobolev, Arkadij; Pikun, Nadiia; Organic & biomolecular chemistry 23 (2025) 6174–6190; doi:10.1039/d5ob00409h

data_7160578
_publ_section_title
;
 Multistep synthesis of cationic lipid-like compounds based on a
 difluorotetrahydropyridine scaffold as amphiphilic nanocarriers.
;
_journal_issue                   25
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6174
_journal_page_last               6190
_journal_paper_doi               10.1039/d5ob00409h
_journal_volume                  23
_journal_year                    2025
_chemical_formula_sum            'C19 H21 F2 N O4'
_chemical_formula_weight         365.37
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2024-11-01 deposited with the CCDC.	2025-06-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.2959(14)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.7661(2)
_cell_length_b                   6.89850(9)
_cell_length_c                   16.2957(2)
_cell_measurement_reflns_used    14875
_cell_measurement_temperature    160(2)
_cell_measurement_theta_max      76.2620
_cell_measurement_theta_min      2.7050
_cell_volume                     1841.54(4)
_computing_cell_refinement       'CrysAlisPro 1.171.40.74a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.74a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.74a (Rigaku OD, 2020)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_temperature      160(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0219
_diffrn_reflns_av_unetI/netI     0.0131
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       3
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            17724
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.473
_diffrn_reflns_theta_min         2.697
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.892
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84452
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.71a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_description       block
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.382
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       0.00083(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         3734
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0362
_refine_ls_R_factor_gt           0.0354
_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^)+(0.0548P)^2^+0.5380P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0993
_refine_ls_wR_factor_ref         0.0999
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3578
_reflns_number_total             3734
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob00409h2.cif
_cod_data_source_block           pn140b
_cod_depositor_comments
'Adding full bibliography for 7160578--7160579.cif.'
_cod_original_cell_volume        1841.55(4)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7160578
_shelx_shelxl_version_number     2018/3
_shelx_res_checksum              66843