L-proline, a resolution agent able to target both enantiomers of mandelic acid: an exciting case of stoichiometry controlled chiral resolution.
Zhou, Fuli; Collard, Laurent; Robeyns, Koen; Leyssens, Tom; Shemchuk, Oleksii; Chemical Communications  (2022) –; doi:10.1039/D2CC02942A

data_7130318
_publ_section_title
;
 L-proline, a resolution agent able to target both enantiomers of mandelic
 acid: an exciting case of stoichiometry controlled chiral resolution.
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC02942A
_journal_year                    2022
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C8 H8 O3, C5 H9 N O2'
_chemical_formula_sum            'C13 H17 N O5'
_chemical_formula_weight         267.27
_chemical_name_systematic        'R-mandelic acid , L-proline (1:1)'
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     'dual space'
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2022-05-23 deposited with the CCDC.	2022-07-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.8248(5)
_cell_length_b                   7.9556(4)
_cell_length_c                   20.9680(11)
_cell_measurement_reflns_used    3659
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      25.6360
_cell_measurement_theta_min      3.2100
_cell_volume                     1305.28(13)
_computing_cell_refinement       'CrysAlisPro 1.171.40.16b (Rigaku OD, 2018)'
_computing_data_collection       MAR
_computing_data_reduction        'CrysAlisPro 1.171.40.16b (Rigaku OD, 2018)'
_computing_molecular_graphics    'MERCURY (Macrae et al., 2008)'
_computing_publication_material
;

'MERCURY (Macrae et al., 2008), Platon (Spek, 2009)'
;
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      297(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'MAR345 image plate'
_diffrn_measurement_method
;
'75 images, \D\F 2.5\% '
;
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_av_unetI/netI     0.0242
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            9519
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.091
_diffrn_reflns_theta_min         3.214
_diffrn_source                   'Incoatec microfocus source'
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87502
_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    1.360
_exptl_crystal_description       block
_exptl_crystal_F_000             568
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: methanol'
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.166
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details
;
 Flack x determined using 807 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.6(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         2586
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.092
_refine_ls_R_factor_all          0.0535
_refine_ls_R_factor_gt           0.0444
_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^)+(0.0445P)^2^+0.5658P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1134
_refine_ls_wR_factor_ref         0.1205
_reflns_Friedel_coverage         0.710
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                2249
_reflns_number_total             2586
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc02942a2.cif
_cod_data_source_block           Fuli_RmanLprol_2
_cod_original_cell_volume        1305.28(12)
_cod_database_code               7130318
_shelx_shelxl_version_number     2018/3
_shelx_res_checksum              64881
_shelx_hkl_checksum              17793