Access to chiral phthalidyl ester prodrugs <i>via</i> an isothiourea-catalyzed dynamic kinetic resolution reaction.
Cai, Hui; Song, Chaoyang; Ling, Dan; Deng, Youlin; Jin, Zhichao; Li, Tingting; Organic & biomolecular chemistry 23 (2025) 3680–3688; doi:10.1039/d4ob02057j

data_7160449
_publ_section_title
;
 Access to chiral phthalidyl ester prodrugs <i>via</i> an
 isothiourea-catalyzed dynamic kinetic resolution reaction.
;
_journal_issue                   15
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3680
_journal_page_last               3688
_journal_paper_doi               10.1039/d4ob02057j
_journal_volume                  23
_journal_year                    2025
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C15 H10 O4'
_chemical_formula_sum            'C15 H10 O4'
_chemical_formula_weight         254.23
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-05-29
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-05-29 deposited with the CCDC.	2025-03-10 downloaded from the CCDC.
;
_cell_angle_alpha                96.968(3)
_cell_angle_beta                 93.261(3)
_cell_angle_gamma                91.060(3)
_cell_formula_units_Z            1
_cell_length_a                   4.0759(2)
_cell_length_b                   7.1675(4)
_cell_length_c                   10.4870(6)
_cell_measurement_reflns_used    3368
_cell_measurement_temperature    303.00
_cell_measurement_theta_max      68.207
_cell_measurement_theta_min      4.255
_cell_volume                     303.51(3)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_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 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      303.00
_diffrn_measured_fraction_theta_full 0.948
_diffrn_measured_fraction_theta_max 0.948
_diffrn_measurement_device_type  Bruker
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_av_unetI/netI     0.0409
_diffrn_reflns_Laue_measured_fraction_full 0.948
_diffrn_reflns_Laue_measured_fraction_max 0.948
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3501
_diffrn_reflns_point_group_measured_fraction_full 0.804
_diffrn_reflns_point_group_measured_fraction_max 0.804
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.207
_diffrn_reflns_theta_min         4.255
_diffrn_source_current           1.1
_diffrn_source_power             0.05500000000000001
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.847
_exptl_absorpt_correction_T_max  0.7530
_exptl_absorpt_correction_T_min  0.5208
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0956 before and 0.0495 after correction.
The Ratio of minimum to maximum transmission is 0.6916.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_description       block
_exptl_crystal_F_000             132
_refine_diff_density_max         0.112
_refine_diff_density_min         -0.128
_refine_diff_density_rms         0.030
_refine_ls_abs_structure_details
;
 Flack x determined using 710 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         1768
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0329
_refine_ls_R_factor_gt           0.0327
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0558P)^2^+0.0212P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0907
_refine_ls_wR_factor_ref         0.0908
_reflns_Friedel_coverage         0.695
_reflns_Friedel_fraction_full    0.661
_reflns_Friedel_fraction_max     0.659
_reflns_number_gt                1760
_reflns_number_total             1768
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob02057j3.cif
_cod_data_source_block           cu_240529chmx_0m
_cod_depositor_comments          'Adding full bibliography for 7160449.cif.'
_cod_database_code               7160449
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C11(H11), C12(H12), C13(H13), C14(H14),
 C15(H15)
;
_shelx_res_checksum              51408
_olex2_submission_special_instructions 'No special instructions were received'