Synthesis and characterization of long chain <i>O</i>-acyl-L-alaninols and investigation of drug encapsulation and release by equimolar <i>O</i>-myristoyl-L-alaninol/SDS catanionic liposomes.
Choudhury, Suman Kumar; Chinapaka, Ravindar; Manasa, Konga; Swamy, Musti J.; Soft matter 21 (2025) 5728–5742; doi:10.1039/d5sm00499c

data_1574927
_publ_section_title
;
 Synthesis and characterization of long chain <i>O</i>-acyl-L-alaninols
 and investigation of drug encapsulation and release by equimolar
 <i>O</i>-myristoyl-L-alaninol/SDS catanionic liposomes.
;
_journal_issue                   28
_journal_name_full               'Soft matter'
_journal_page_first              5728
_journal_page_last               5742
_journal_paper_doi               10.1039/d5sm00499c
_journal_volume                  21
_journal_year                    2025
_chemical_absolute_configuration syn
_chemical_formula_moiety         '2(Cl), 2(C20 H42 N O2)'
_chemical_formula_sum            'C40 H84 Cl2 N2 O4'
_chemical_formula_weight         727.99
_chemical_name_systematic        C20H42NO2Cl
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2023-05-31
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2018.12.18 svn.r3554 for Rigaku Oxford Diffraction, GUI svn.r1)
;
_audit_update_record
;
2024-11-13 deposited with the CCDC.	2025-06-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.383(6)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.0685(5)
_cell_length_b                   7.4023(4)
_cell_length_c                   34.118(3)
_cell_measurement_reflns_used    3765
_cell_measurement_temperature    297.6(5)
_cell_measurement_theta_max      23.4360
_cell_measurement_theta_min      2.3890
_cell_volume                     2280.2(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      297.6(5)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.961
_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     10.00  54.00   0.50   31.91    --  -14.97  45.00   0.00   88
  2  \w     -8.00  18.00   0.50   31.91    --  -14.97  86.00 -59.00   52
  3  \w    -13.00  36.00   0.50   31.91    --  -14.97  45.00 -90.00   98
  4  \w     16.00  44.00   0.50   31.91    --   16.22  86.00 -59.00   56
  5  \w    -46.00 -13.00   0.50   31.91    --  -14.97  86.00 -59.00   66
  6  \w    -10.00  47.00   0.50   31.91    --   16.22  30.00  60.00  114
  7  \w     62.00  88.00   0.50   31.91    --   16.22  30.00  60.00   52
  8  \w     17.00  47.00   0.50   31.91    --   16.22-125.00 120.00   60
  9  \w    -34.00  17.00   0.50   31.91    --  -14.97 -94.00  60.00  102
 10  \w     28.00  71.00   0.50   31.91    --   16.22-125.00  30.00   86
 11  \w     34.00  70.00   0.50   31.91    --   16.22-125.00   0.00   72
 12  \w    -46.00  19.00   0.50   31.91    --   16.22 -45.00  90.00  130
 13  \w    -26.00  17.00   0.50   31.91    --  -14.97 -86.00-177.00   86
 14  \w    -35.00  -2.00   0.50   31.91    --   16.22 -86.00-177.00   66
 15  \w    -37.00  42.00   0.50   31.91    --   16.22 -61.00-180.00  158
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0173217000
_diffrn_orient_matrix_UB_12      0.0409843000
_diffrn_orient_matrix_UB_13      -0.0186656000
_diffrn_orient_matrix_UB_21      -0.0301774000
_diffrn_orient_matrix_UB_22      0.0754897000
_diffrn_orient_matrix_UB_23      0.0092538000
_diffrn_orient_matrix_UB_31      0.0704115000
_diffrn_orient_matrix_UB_32      0.0424664000
_diffrn_orient_matrix_UB_33      0.0015312000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0789
_diffrn_reflns_av_unetI/netI     0.0864
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_number            9743
_diffrn_reflns_point_group_measured_fraction_full 0.922
_diffrn_reflns_point_group_measured_fraction_max 0.860
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.937
_diffrn_reflns_theta_min         2.398
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.179
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.44007
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.35a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.060
_exptl_crystal_description       plate
_exptl_crystal_F_000             808
_refine_diff_density_max         0.318
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details
;
 Flack x determined using 798 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.11(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.965
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     224
_refine_ls_number_reflns         4286
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.965
_refine_ls_R_factor_all          0.1005
_refine_ls_R_factor_gt           0.0638
_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^)+(0.0755P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1446
_refine_ls_wR_factor_ref         0.1660
_reflns_Friedel_coverage         0.661
_reflns_Friedel_fraction_full    0.831
_reflns_Friedel_fraction_max     0.743
_reflns_number_gt                2667
_reflns_number_total             4286
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sm00499c2.cif
_cod_data_source_block           mjs140a
_cod_depositor_comments
'Adding full bibliography for 1574926--1574927.cif.'
_cod_original_cell_volume        2280.1(2)
_cod_database_code               1574927
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.61
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Riding coordinates:
 C18(H18A)
2.b Ternary CH refined with riding coordinates:
 C19(H19)
2.c Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B), C6(H6A,H6B), C5(H5A,H5B), C2(H2A,H2B), C7(H7A,H7B),
 C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B), C12(H12A,H12B), C11(H11A,H11B),
 C15(H15A,H15B), C13(H13A,H13B), C14(H14A,H14B), C16(H16A,H16B)
2.d Idealised Me refined as rotating group:
 N1(H1A,H1B,H1C), C20(H20A,H20B,H20C), C17(H17A,H17B,H17C)
;
_shelx_res_checksum              43126
_shelx_hkl_checksum              26851
_olex2_submission_original_sample_id MJS140A
_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 1.741
_oxdiff_exptl_absorpt_empirical_full_min 0.341