Solvent-triggered breakdown of solid solution behaviour enables direct enantioselective crystallization of <i>RS</i>-phenprocoumon.
Jiang, Yihua; Souare, Sokhna; Robeyns, Koen; Leng, Fucheng; Collard, Laurent; Leyssens, Tom; Chemical communications (Cambridge, England) 62 (2026) 6613–6616; doi:10.1039/d6cc00933f

data_7135576
_publ_section_title
;
 Solvent-triggered breakdown of solid solution behaviour enables direct
 enantioselective crystallization of <i>RS</i>-phenprocoumon.
;
_journal_issue                   24
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              6613
_journal_page_last               6616
_journal_paper_doi               10.1039/d6cc00933f
_journal_volume                  62
_journal_year                    2026
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C20 H25 N2 O2, C18 H15 O3, C2 H6 O'
_chemical_formula_sum            'C40 H46 N2 O6'
_chemical_formula_weight         650.79
_chemical_name_common            'Quinidine Phenprocoumon ethanol solvate'
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 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.	2026-03-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 111.669(13)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   12.3135(13)
_cell_length_b                   9.8662(10)
_cell_length_c                   15.529(2)
_cell_measurement_reflns_used    2598
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      25.0380
_cell_measurement_theta_min      3.2840
_cell_volume                     1753.3(4)
_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      150(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'MAR345 image plate'
_diffrn_measurement_method
;
'100 images, \D\F 2.0\% '
;
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0860
_diffrn_reflns_av_unetI/netI     0.1123
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            12645
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.235
_diffrn_reflns_theta_max         25.235
_diffrn_reflns_theta_min         3.310
_diffrn_source                   'Incoatec microfocus source'
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.42701
_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    1.233
_exptl_crystal_description       needle
_exptl_crystal_F_000             696
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: ethanol'
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.317
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details
;
 Flack x determined using 1315 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -1.3(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.987
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     511
_refine_ls_number_reflns         6300
_refine_ls_number_restraints     70
_refine_ls_restrained_S_all      0.982
_refine_ls_R_factor_all          0.1139
_refine_ls_R_factor_gt           0.0599
_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^)+(0.0469P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1113
_refine_ls_wR_factor_ref         0.1296
_reflns_Friedel_coverage         0.882
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                3953
_reflns_number_total             6300
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d6cc00933f2.cif
_cod_data_source_block           yj_Qd_phC_EtOH
_cod_depositor_comments
'Adding full bibliography for 7135572--7135577.cif.'
_cod_original_cell_volume        1753.2(4)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7135576
_shelx_shelxl_version_number     2019/3
_shelx_res_checksum              16350
_shelx_hkl_checksum              9950