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_7250784
_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_absolute_configuration rm
_chemical_formula_moiety         'C40 H30 O5, C2 H6 O, 0.5(C2 H5 O)'
_chemical_formula_sum            'C43 H38.5 O6.5'
_chemical_formula_weight         659.24
_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
_audit_creation_date             2024-03-29
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2024-03-29 deposited with the CCDC.	2025-07-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.566(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   18.4127(6)
_cell_length_b                   10.4885(4)
_cell_length_c                   36.6054(10)
_cell_measurement_reflns_used    17537
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.1430
_cell_measurement_theta_min      2.2140
_cell_volume                     6990.4(4)
_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    'SHELXT 2018/2 (Sheldrick, 2018)'
_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 0.920
_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    -41.00  16.00   0.50   19.50    --   -9.75 -79.00 -49.00  114
  2  \w    -34.00  42.00   0.50   19.50    --   -9.75  79.00  74.00  152
  3  \w    -11.00  15.00   0.50   19.50    --    9.83 -79.00 -49.00   52
  4  \w      1.00  34.00   0.50   19.50    --    9.83  79.00  74.00   66
  5  \w    -39.00  14.00   0.50   19.50    --   -9.75 -77.00-180.00  106
  6  \w    -28.00  -2.00   0.50   19.50    --   -9.75 -77.00  90.00   52
  7  \w    -22.00  51.00   0.50   19.50    --   -9.75  37.00  30.00  146
  8  \w     -2.00  80.00   0.50   19.50    --    9.83  19.00 -60.00  164
  9  \w     17.00  57.00   0.50   19.50    --    9.83  37.00 -30.00   80
;
_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      -0.0204489000
_diffrn_orient_matrix_UB_12      0.0562450000
_diffrn_orient_matrix_UB_13      -0.0050141000
_diffrn_orient_matrix_UB_21      0.0218962000
_diffrn_orient_matrix_UB_22      0.0122236000
_diffrn_orient_matrix_UB_23      -0.0139978000
_diffrn_orient_matrix_UB_31      -0.0248899000
_diffrn_orient_matrix_UB_32      -0.0354772000
_diffrn_orient_matrix_UB_33      -0.0127770000
_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  0.0418
_diffrn_reflns_av_unetI/netI     0.0533
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.920
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_limit_l_min       -45
_diffrn_reflns_number            30571
_diffrn_reflns_point_group_measured_fraction_full 0.822
_diffrn_reflns_point_group_measured_fraction_max 0.737
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.494
_diffrn_reflns_theta_min         2.237
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52067
_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_density_diffrn    1.253
_exptl_crystal_description       block
_exptl_crystal_F_000             2788
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.219
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details
;
 Flack x determined using 2525 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.3(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.931
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     929
_refine_ls_number_reflns         11840
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.931
_refine_ls_R_factor_all          0.0721
_refine_ls_R_factor_gt           0.0464
_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^)+(0.0764P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1115
_refine_ls_wR_factor_ref         0.1236
_reflns_Friedel_coverage         0.519
_reflns_Friedel_fraction_full    0.624
_reflns_Friedel_fraction_max     0.532
_reflns_number_gt                8259
_reflns_number_total             11840
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ra04790k2.cif
_cod_data_source_block           pm_c7_5_auto
_cod_original_formula_sum        'C43 H38.50 O6.50'
_cod_database_code               7250784
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H O'
_shelx_estimated_absorpt_t_max   0.975
_shelx_estimated_absorpt_t_min   0.967
_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
2. Others
 Fixed Sof: O0(0.25) O8(0.75) C33(0.5) H33A(0.5) H33B(0.5) H33C(0.5) C35(0.5)
 H35A(0.5) H35B(0.5) H35C(0.5)
3.a Ternary CH refined with riding coordinates:
 C9(H9), C26(H26), C10(H10A), C25(H25)
3.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C12(H12A,H12B), C30(H30A,H30B), C28(H28A,H28B), C50(H50A,H50B)
3.c Aromatic/amide H refined with riding coordinates:
 C11"(H11"), C12"(H12"), C4'(H4'), C8(H8), C2(H2), C21(H21), C16'(H16'),
 C4"(H4"), C16"(H16"), C24(H24), C6(H6), C3"(H3"), C5'(H5'), C3'(H3'), C8'(H8'),
  C20(H20), C13"(H13"), C23(H23), C7(H7), C11'(H11'), C7'(H7'), C5"(H5"),
 C19(H19), C14"(H14"), C4(H4), C12'(H12'), C17(H17), C16(H16), C8"(H8"),
 C13'(H13'), C15'(H15'), C18(H18), C14'(H14'), C1A(H1A), C6'(H6'), C15"(H15"),
 C6"(H6"), C7"(H7"), C52(H52), C54(H54), C54(H54A)
3.d Idealised Me refined as rotating group:
 C32(H32A,H32B,H32C), C51(H51A,H51B,H51C), C1B(H1BA,H1BB,H1BC), C53(H53A,H53B,
 H53C), C33(H33A,H33B,H33C), C35(H35A,H35B,H35C)
3.e Idealised tetrahedral OH refined as rotating group:
 O10(H10), O5(H5), O22(H22A), O21(H21A), O20(H20A)
;
_shelx_res_checksum              29404
_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 2.335
_oxdiff_exptl_absorpt_empirical_full_min 0.537