A bug in enantiomer separation: double salt formation ‒ diastereomeric and double salt structures of 1-cyclohexylethylammonium 2- and 4-chloromandelate
Bereczki, Laura; Zodge, Amit; Kőrösi, Márton; Holczbauer, Tamás; De, Sourav; Székely, Edit; Bombicz, Petra; CrystEngComm 23 (2021) 5367–5376; doi:10.1039/D1CE00145K

data_7243246
_publ_section_title
;
 A bug in enantiomer separation: double salt formation -- diastereomeric
 and double salt structures of 1-cyclohexylethylammonium 2- and
 4-chloromandelate
;
_journal_issue                   31
_journal_name_full               CrystEngComm
_journal_page_first              5367
_journal_page_last               5376
_journal_paper_doi               10.1039/D1CE00145K
_journal_volume                  23
_journal_year                    2021
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C8 H18 N 1+, C8 H6 Cl O3 1-'
_chemical_formula_sum            'C16 H24 Cl N O3'
_chemical_formula_weight         313.81
_chemical_melting_point          411(1)
_chemical_name_common
;
(S)-(1-cyclohexylethyl)ammonium (R,S)-2-chloromandelate
;
_chemical_name_systematic
;
(S)-(1-cyclohexylethyl)ammonium (R,S)-2-(2-chlorophenyl)-2-hydroxyacetate
;
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2021-01-29 deposited with the CCDC.	2021-07-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.5330(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   24.2266(8)
_cell_length_b                   10.0661(8)
_cell_length_c                   13.3665(8)
_cell_measurement_reflns_used    18379
_cell_measurement_temperature    119(2)
_cell_measurement_theta_max      71.835
_cell_measurement_theta_min      3.310
_cell_volume                     3256.5(3)
_computing_cell_refinement
;
RAPID-AUTO (Rigaku Corp., Tokyo, Japan, 2015)
;
_computing_data_collection
;
RAPID-AUTO (Rigaku Corp., Tokyo, Japan, 2015)
;
_computing_data_reduction
;
RAPID-AUTO (Rigaku Corp., Tokyo, Japan, 2015)
;
_computing_molecular_graphics
;
Spek, A.L. (2003). J.Appl.Cryst. 36,7-13.
;
_computing_publication_material
;
C. F. Macrae, J. Appl. Cryst., 41, 466-470, 2008
;
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution
;
  Sheldrick, G. M. (2015). Acta Cryst. A71, 3-8.
;
_diffrn_ambient_temperature      119(2)
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.970
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_device       RAXIS-RAPID
_diffrn_measurement_method       dtprofit.ref
_diffrn_radiation_detector       RX
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_source         'Sealed Tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0513
_diffrn_reflns_av_unetI/netI     0.0612
_diffrn_reflns_Laue_measured_fraction_full 0.970
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            18879
_diffrn_reflns_point_group_measured_fraction_full 0.952
_diffrn_reflns_point_group_measured_fraction_max 0.949
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.245
_diffrn_reflns_theta_min         3.310
_exptl_absorpt_coefficient_mu    2.157
_exptl_absorpt_correction_T_max  0.964
_exptl_absorpt_correction_T_min  0.882
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
  NUMABS, Numerical Absorption correction Program (T.Higashi, 2011)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_description       platelet
_exptl_crystal_F_000             1344
_exptl_crystal_size_max          0.61
_exptl_crystal_size_mid          0.48
_exptl_crystal_size_min          0.44
_exptl_transmission_factor_max   0.964339
_exptl_transmission_factor_min   0.881501
_refine_diff_density_max         0.277
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
;
 Flack x determined using 1843 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.099(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     413
_refine_ls_number_reflns         5644
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0526
_refine_ls_R_factor_gt           0.0468
_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^)+(0.0446P)^2^+1.2400P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1070
_refine_ls_wR_factor_ref         0.1100
_reflns_Friedel_coverage         0.846
_reflns_Friedel_fraction_full    0.931
_reflns_Friedel_fraction_max     0.927
_reflns_number_gt                5111
_reflns_number_total             5644
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ce00145k2.cif
_cod_data_source_block           shelx_CCDC4
_cod_depositor_comments
'Adding full bibliography for 7243242--7243247.cif.'
_cod_original_sg_symbol_H-M      'C 2'
_cod_database_code               7243246
_shelx_res_checksum              20040
_shelx_hkl_checksum              91046