Chiral Resolution of Racemic Ibuprofen Sodium via Diastereomeric Ionic Cocrystallization with Proline
Wen, Ting; Leyssens, Tom; Robeyns, Koen; Collard, Laurent; Leng, Fucheng; Chemical Communications  (2026) –; doi:10.1039/D6CC01175F

data_7135712
_publ_section_title
;
 Chiral resolution of racemic ibuprofen sodium <i>via</i> diastereomeric
 ionic cocrystallization with proline.
;
_journal_issue                   32
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              8280
_journal_page_last               8283
_journal_paper_doi               10.1039/d6cc01175f
_journal_volume                  62
_journal_year                    2026
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C18 H26 N Na O4'
_chemical_formula_sum            'C18 H26 N Na O4'
_chemical_formula_weight         343.39
_chemical_name_common            'S-ibuprofen L-proline sodium'
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_method           SHELXL-2019/3
_audit_update_record
;
2026-02-10 deposited with the CCDC.	2026-04-07 downloaded from the CCDC.
;
_cell_angle_alpha                83.265(8)
_cell_angle_beta                 84.387(8)
_cell_angle_gamma                85.997(8)
_cell_formula_units_Z            2
_cell_length_a                   5.7825(6)
_cell_length_b                   9.8484(10)
_cell_length_c                   17.0500(15)
_cell_measurement_reflns_used    3083
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      26.3520
_cell_measurement_theta_min      2.4050
_cell_volume                     957.97(16)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       MAR
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'MERCURY (Macrae et al., 2008)'
_computing_publication_material
;
'MERCURY (Macrae et al., 2008), Platon (Spek, 2009)'
;
_computing_structure_refinement  'SHELXL-2019/3 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      297(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'MAR345 image plate'
_diffrn_measurement_method
;
'200 images, \D\F 1.2\% '
'150 images, \D\F 1.2\% (2nd orientation)'
;
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.0498
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            6539
_diffrn_reflns_point_group_measured_fraction_full 0.946
_diffrn_reflns_point_group_measured_fraction_max 0.946
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.251
_diffrn_reflns_theta_min         2.416
_diffrn_source                   'Incoatec microfocus source'
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81047
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.190
_exptl_crystal_description       rod
_exptl_crystal_F_000             368
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Isopropyl alcohol/hexane (30/70)'
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details
;
 Flack x determined using 2019 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.4(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     618
_refine_ls_number_reflns         6539
_refine_ls_number_restraints     295
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0652
_refine_ls_R_factor_gt           0.0517
_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^)+(0.0540P)^2^+0.2825P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1249
_refine_ls_wR_factor_ref         0.1356
_reflns_Friedel_coverage         0.899
_reflns_Friedel_fraction_full    0.895
_reflns_Friedel_fraction_max     0.896
_reflns_number_gt                5359
_reflns_number_total             6539
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d6cc01175f2.cif
_cod_data_source_block           tw_sibuna_lpro_r_all2_tw
_cod_depositor_comments
'Adding full bibliography for 7135711--7135712.cif.'
_cod_database_code               7135712
_shelx_shelxl_version_number     2019/3
_shelx_res_checksum              3384