Methyl itaconate–anthracene adducts (MIAs) facilitate the enantiomeric separation of 1,1′-bi-2-naphthols via thin-layer chromatography (TLC) with trends predicted by molecular dynamics simulations
Sinthopweha, Wichai; Khamto, Nopawit; Rithchumpon, Puracheth; Meepowpan, Puttinan; RSC Advances 15 (2025) 28063–28074; doi:10.1039/D5RA04790K

data_7250787
_publ_section_title
;
 Methyl itaconate--anthracene adducts (MIAs) facilitate the enantiomeric
 separation of 1,1&#x2032;-bi-2-naphthols via thin-layer chromatography
 (TLC) with trends predicted by molecular dynamics simulations
;
_journal_issue                   34
_journal_name_full               'RSC Advances'
_journal_page_first              28063
_journal_page_last               28074
_journal_paper_doi               10.1039/D5RA04790K
_journal_volume                  15
_journal_year                    2025
_chemical_formula_moiety         'C40 H30 O5, H2 O, C2 H2 O'
_chemical_formula_sum            'C42 H34 O7'
_chemical_formula_weight         650.69
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2025-02-13
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2025-02-13 deposited with the CCDC.	2025-07-29 downloaded from the CCDC.
;
_cell_angle_alpha                90.877(3)
_cell_angle_beta                 106.567(3)
_cell_angle_gamma                112.991(3)
_cell_formula_units_Z            2
_cell_length_a                   10.4163(4)
_cell_length_b                   12.2293(4)
_cell_length_c                   15.1051(5)
_cell_measurement_reflns_used    10671
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.2360
_cell_measurement_theta_min      1.8260
_cell_volume                     1680.19(12)
_computing_cell_refinement       'CrysAlisPro 1.171.41.111a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.111a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.111a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.913
_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    -73.00  -3.00   0.50   11.67    --   -9.75 -41.00  84.00  140
  2  \w    -14.00  12.00   0.50   11.67    --   -9.75  41.00-122.00   52
  3  \w    -50.00 -15.00   0.50   11.67    --    9.83 -41.00  84.00   70
  4  \w     15.00  56.00   0.50   11.67    --    9.83  41.00-122.00   82
  5  \w    -80.00 -43.00   0.50   11.67    --   -9.75 -19.00 -90.00   74
  6  \w    -41.00  16.00   0.50   11.67    --   -9.75 -77.00-150.00  114
  7  \w    -51.00 -25.00   0.50   11.67    --   -9.75 125.00   0.00   52
  8  \w    -46.00  -9.00   0.50   11.67    --   -9.75 -37.00-150.00   74
  9  \w    -73.00 -11.00   0.50   11.67    --   -9.75 -37.00   0.00  124
 10  \w    -40.00  13.00   0.50   11.67    --   -9.75 -77.00 120.00  106
 11  \w    -23.00   2.00   0.50   11.67    --   -9.75 -19.00 -90.00   50
 12  \w    -58.00 -24.00   0.50   11.67    --   -9.75 125.00  30.00   68
 13  \w    -49.00   6.00   0.50   11.67    --    9.83 -37.00 -30.00  110
 14  \w     12.00  39.00   0.50   11.67    --    9.83 -99.00 -60.00   54
 15  \w      2.00  77.00   0.50   11.67    --    9.83  19.00 -60.00  150
 16  \w    -32.00  -2.00   0.50   11.67    --    9.83 119.00  -1.35   60
 17  \w    -32.00   1.00   0.50   11.67    --    9.83 116.00  64.01   66
 18  \w      1.00  38.00   0.50   11.67    --    9.83 -99.00   0.00   74
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'SuperNova, 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      -0.0525627000
_diffrn_orient_matrix_UB_12      -0.0124432000
_diffrn_orient_matrix_UB_13      0.0239339000
_diffrn_orient_matrix_UB_21      -0.0173972000
_diffrn_orient_matrix_UB_22      -0.0621809000
_diffrn_orient_matrix_UB_23      -0.0082038000
_diffrn_orient_matrix_UB_31      0.0549028000
_diffrn_orient_matrix_UB_32      0.0056447000
_diffrn_orient_matrix_UB_33      0.0425504000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0396
_diffrn_reflns_av_unetI/netI     0.0532
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.913
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            23741
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.913
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.524
_diffrn_reflns_theta_min         2.148
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.09507
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.111a (Rigaku Oxford Diffraction, 2021)
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    1.286
_exptl_crystal_description       block
_exptl_crystal_F_000             684
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.520
_refine_diff_density_min         -0.515
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     447
_refine_ls_number_reflns         7093
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.1094
_refine_ls_R_factor_gt           0.0661
_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^)+(0.1033P)^2^+0.1961P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1817
_refine_ls_wR_factor_ref         0.2087
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4198
_reflns_number_total             7093
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ra04790k2.cif
_cod_data_source_block           670610_pm_c6_auto
_cod_original_cell_volume        1680.19(11)
_cod_database_code               7250787
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H O'
_shelx_estimated_absorpt_t_max   0.996
_shelx_estimated_absorpt_t_min   0.958
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups, All O(H,H) groups
2.a Free rotating group:
 O6(H6A,H6B)
2.b Ternary CH refined with riding coordinates:
 C10(H10), C9(H9)
2.c Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C12(H12A,H12B)
2.d Aromatic/amide H refined with riding coordinates:
 C3'(H3'), C8'(H8'), C8"(H8"), C4'(H4'), C5(H5A), C4(H4), C8(H8), C6"(H6"),
 C5'(H5'), C3"(H3"), C4"(H4"), C1(H1), C6'(H6'), C6(H6), C2(H2), C7(H7), C3(H3),
  C7"(H7"), C19(H19), C20(H20), C18(H18), C17(H17)
2.e Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
2.f Idealised tetrahedral OH refined as rotating group:
 O5(H5)
;
_shelx_res_checksum              9673
_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 7.675
_oxdiff_exptl_absorpt_empirical_full_min 0.354