Synthesis and application of methyl itaconate-anthracene adducts in configuration assignment of chiral secondary alcohols by <sup>1</sup>H NMR.
Rithchumpon, Puracheth; Intakaew, Neeranuth; Khamto, Nopawit; Yimklan, Saranpong; Nimmanpipug, Piyarat; Thavornyutikarn, Praput; Meepowpan, Puttinan; Organic & biomolecular chemistry 19 (2021) 8955–8967; doi:10.1039/d1ob01387d

data_7158304
_publ_section_title
;
 Synthesis and application of methyl itaconate-anthracene adducts in
 configuration assignment of chiral secondary alcohols by <sup>1</sup>H
 NMR.
;
_journal_issue                   41
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              8955
_journal_page_last               8967
_journal_paper_doi               10.1039/d1ob01387d
_journal_volume                  19
_journal_year                    2021
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C24 H26 O4'
_chemical_formula_sum            'C24 H26 O4'
_chemical_formula_weight         378.45
_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
_audit_creation_date             2019-07-01
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-07-03 deposited with the CCDC.	2021-09-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.0659(2)
_cell_length_b                   10.1740(3)
_cell_length_c                   20.3251(5)
_cell_measurement_reflns_used    12369
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.4620
_cell_measurement_theta_min      2.2210
_cell_volume                     2081.50(9)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.937
_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    -49.00  10.00   0.50    6.10    --   -9.67 110.00 -41.00  118
  2  \w    -50.00   8.00   0.50    6.10    --   -9.67 112.00-134.00  116
  3  \w      0.00  80.00   0.50    6.10    --   10.38  21.00 131.00  160
  4  \w      3.00  59.00   0.50    6.10    --   10.38-125.00  90.00  112
  5  \w      3.00  59.00   0.50    6.10    --   10.38-125.00 -60.00  112
  6  \w    -15.00  75.00   0.50    6.10    --   10.38  77.00-120.00  180
  7  \w    -54.00  23.00   0.50    6.10    --   10.38 -37.00 -60.00  154
  8  \w    -15.00  37.00   0.50    6.10    --   10.38  77.00   0.00  104
  9  \w    -60.00  23.00   0.50    6.10    --   10.38 -19.00 120.00  166
;
_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      0.0131667000
_diffrn_orient_matrix_UB_12      0.0017875000
_diffrn_orient_matrix_UB_13      -0.0342644000
_diffrn_orient_matrix_UB_21      0.0147782000
_diffrn_orient_matrix_UB_22      -0.0681661000
_diffrn_orient_matrix_UB_23      0.0005041000
_diffrn_orient_matrix_UB_31      -0.0676371000
_diffrn_orient_matrix_UB_32      -0.0145566000
_diffrn_orient_matrix_UB_33      -0.0065533000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0391
_diffrn_reflns_av_unetI/netI     0.0354
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.937
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            23193
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.928
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.443
_diffrn_reflns_theta_min         2.239
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.48863
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
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    1.208
_exptl_crystal_description       block
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.304
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details
;
 Flack x determined using 1087 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_coef       0.013(3)
_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   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         4427
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0720
_refine_ls_R_factor_gt           0.0506
_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^)+(0.0722P)^2^+0.1176P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1279
_refine_ls_wR_factor_ref         0.1412
_reflns_Friedel_coverage         0.743
_reflns_Friedel_fraction_full    0.986
_reflns_Friedel_fraction_max     0.918
_reflns_number_gt                3228
_reflns_number_total             4427
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob01387d2.cif
_cod_data_source_block           pm01as210619r1
_cod_depositor_comments
'Adding full bibliography for 7158301--7158304.cif.'
_cod_database_code               7158304
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H O '
_shelx_estimated_absorpt_t_max   0.976
_shelx_estimated_absorpt_t_min   0.961
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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
2.a Ternary CH refined with riding coordinates:
 C9(H9), C10(H10), C1'(H1')
2.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C12(H12A,H12B), C3'(H3'A,H3'B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C1(H1), C8(H8), C5(H5), C3(H3), C2(H2), C7(H7), C6(H6)
2.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C2'(H2'A,H2'B,H2'C), C4'(H4'A,H4'B,H4'C)
;
_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 1.888
_oxdiff_exptl_absorpt_empirical_full_min 0.519