Solvent-controlled stereoselective supramolecular synthesis: a case of diastereomeric dimers of 16-S-dihydrosteviol
Gerasimova, Daria P.; Zakharychev, Dmitry V.; Saifina, Alina F.; Fayzullin, Robert R.; Lodochnikova, Olga; CrystEngComm  (2026) –; doi:10.1039/D6CE00081A

data_7251832
_publ_section_title
;
 Solvent-controlled stereoselective supramolecular synthesis: a case of
 diastereomeric dimers of 16-S-dihydrosteviol
;
_journal_issue                   18
_journal_name_full               CrystEngComm
_journal_page_first              2995
_journal_page_last               3007
_journal_paper_doi               10.1039/D6CE00081A
_journal_volume                  28
_journal_year                    2026
_chemical_absolute_configuration ad
_chemical_formula_moiety         '0.5(C Cl4), C20 H32 O3'
_chemical_formula_sum            'C20.5 H32 Cl2 O3'
_chemical_formula_weight         397.36
_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   mixed
_audit_creation_date             2026-03-12
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2026-03-12 deposited with the CCDC.	2026-03-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.2364(10)
_cell_length_b                   15.9167(13)
_cell_length_c                   21.4647(16)
_cell_measurement_reflns_used    9691
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.04
_cell_measurement_theta_min      2.30
_cell_volume                     4180.5(6)
_computing_cell_refinement       'SAINT V8.35A (?, 2016)'
_computing_data_reduction        'SAINT V8.35A (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0376
_diffrn_reflns_av_unetI/netI     0.0237
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            54626
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.990
_diffrn_reflns_theta_min         2.289
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.327
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.7098
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1337 before and 0.0560 after correction.
The Ratio of minimum to maximum transmission is 0.9515.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.263
_exptl_crystal_description       prism
_exptl_crystal_F_000             1704
_exptl_crystal_size_max          0.345
_exptl_crystal_size_mid          0.209
_exptl_crystal_size_min          0.102
_refine_diff_density_max         0.824
_refine_diff_density_min         -0.680
_refine_diff_density_rms         0.131
_refine_ls_abs_structure_details
;
 Flack x determined using 3871 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.025(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     482
_refine_ls_number_reflns         9112
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.099
_refine_ls_R_factor_all          0.0514
_refine_ls_R_factor_gt           0.0504
_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^)+(0.0785P)^2^+2.8109P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1317
_refine_ls_wR_factor_ref         0.1326
_reflns_Friedel_coverage         0.806
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                8880
_reflns_number_total             9112
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d6ce00081a2.cif
_cod_data_source_block           kat1_new_a
_cod_depositor_comments
'Adding full bibliography for 7251832--7251835.cif.'
_cod_original_formula_sum        'C20.50 H32 Cl2 O3'
_cod_database_code               7251832
_shelx_shelxl_version_number     2019/1
_shelx_estimated_absorpt_t_max   0.967
_shelx_estimated_absorpt_t_min   0.896
_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. Restrained distances
 O1B-H1B
 0.85 with sigma of 0.02
 O1A-H1A
 0.85 with sigma of 0.02
 O3B-H3B
 0.85 with sigma of 0.02
 O3A-H3A
 0.85 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C5A(H5A), C9A(H9A), C16A(H16A), C5B(H5B), C9B(H9B), C16B(H16B)
3.b Secondary CH2 refined with riding coordinates:
 C1A(H1AA,H1AB), C2A(H2AA,H2AB), C3A(H3AA,H3AB), C6A(H6AA,H6AB), C7A(H7AA,
 H7AB), C11A(H11A,H11B), C12A(H12A,H12B), C14A(H14A,H14B), C15A(H15A,H15B),
 C1B(H1BA,H1BB), C2B(H2BA,H2BB), C3B(H3BA,H3BB), C6B(H6BA,H6BB), C7B(H7BA,H7BB),
  C11B(H11C,H11D), C12B(H12C,H12D), C14B(H14C,H14D), C15B(H15C,H15D)
3.c Idealised Me refined as rotating group:
 C17A(H17A,H17B,H17C), C18A(H18A,H18B,H18C), C20A(H20A,H20B,H20C), C17B(H17D,
 H17E,H17F), C18B(H18D,H18E,H18F), C20B(H20D,H20E,H20F)
;
_shelx_res_checksum              1946
_olex2_submission_special_instructions 'No special instructions were received'