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_7250786
_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         'C H2 Cl2, C40 H30 O5'
_chemical_formula_sum            'C41 H32 Cl2 O5'
_chemical_formula_weight         675.56
_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     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
_cell_angle_beta                 90.917(9)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   13.3491(12)
_cell_length_b                   7.4684(7)
_cell_length_c                   17.3178(19)
_cell_measurement_reflns_used    3828
_cell_measurement_temperature    296.64(10)
_cell_measurement_theta_max      26.7960
_cell_measurement_theta_min      1.9140
_cell_volume                     1726.3(3)
_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_environment      air
_diffrn_ambient_temperature      296.64(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.885
_diffrn_measured_fraction_theta_max 0.807
_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    -56.00 -30.00   0.50   12.40    --   -9.75 158.00  48.00   52
  2  \w     27.00  53.00   0.50   12.40    --    9.83-158.00  14.00   52
  3  \w    -16.00  21.00   0.50   12.40    --    9.83 -36.00  27.00   74
  4  \w    -40.00 -14.00   0.50   12.40    --   -9.75 -77.00   0.00   52
  5  \w    -44.00  -3.00   0.50   12.40    --   -9.75 -37.00 -30.00   82
  6  \w    -58.00 -18.00   0.50   12.40    --   -9.75 125.00 120.00   80
  7  \w    -74.00 -48.00   0.50   12.40    --   -9.75 -37.00 -30.00   52
  8  \w      9.00  51.00   0.50   12.40    --    9.83-125.00 -30.00   84
  9  \w    -12.00  13.00   0.50   12.40    --    9.83 -99.00 120.00   50
;
_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      0.0276164000
_diffrn_orient_matrix_UB_12      -0.0085397000
_diffrn_orient_matrix_UB_13      0.0351677000
_diffrn_orient_matrix_UB_21      -0.0398085000
_diffrn_orient_matrix_UB_22      0.0410351000
_diffrn_orient_matrix_UB_23      0.0200341000
_diffrn_orient_matrix_UB_31      -0.0219552000
_diffrn_orient_matrix_UB_32      -0.0851553000
_diffrn_orient_matrix_UB_33      0.0062624000
_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  0.0894
_diffrn_reflns_av_unetI/netI     0.1390
_diffrn_reflns_Laue_measured_fraction_full 0.885
_diffrn_reflns_Laue_measured_fraction_max 0.807
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            8286
_diffrn_reflns_point_group_measured_fraction_full 0.672
_diffrn_reflns_point_group_measured_fraction_max 0.592
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.434
_diffrn_reflns_theta_min         1.911
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.233
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.35553
_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    1.300
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.460
_refine_diff_density_min         -0.418
_refine_diff_density_rms         0.061
_refine_ls_abs_structure_details
;
 Flack x determined using 637 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(19)
_refine_ls_extinction_coef       0.005(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     436
_refine_ls_number_reflns         4663
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.1571
_refine_ls_R_factor_gt           0.0833
_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^)+(0.1453P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2218
_refine_ls_wR_factor_ref         0.2673
_reflns_Friedel_coverage         0.360
_reflns_Friedel_fraction_full    0.422
_reflns_Friedel_fraction_max     0.340
_reflns_number_gt                2561
_reflns_number_total             4663
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ra04790k2.cif
_cod_data_source_block           ma-c3_auto
_cod_database_code               7250786
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H O'
_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.a Ternary CH refined with riding coordinates:
 C10(H10), C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C12(H12A,H12B), C18(H18A,H18B)
2.c Aromatic/amide H refined with riding coordinates:
 C8"(H8"), C5"(H5"), C3'(H3'), C5(H5A), C4(H4), C4"(H4"), C3"(H3"), C20(H20),
 C7'(H7'), C6"(H6"), C5'(H5'), C7"(H7"), C8(H8), C7(H7), C19(H19), C6(H6),
 C6'(H6'), C1(H1), C3(H3), C2(H2)
2.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
2.e Idealised tetrahedral OH refined as rotating group:
 O5(H5)
;
_shelx_res_checksum              15825
_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 4.451
_oxdiff_exptl_absorpt_empirical_full_min 0.161