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_7251835
_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 rmad
_chemical_formula_moiety         'C20 H32 O3, 1.5(C4 H10 O)'
_chemical_formula_sum            'C26 H47 O4.5'
_chemical_formula_weight         431.63
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2025-08-28
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2025-08-29 deposited with the CCDC.	2026-03-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.427(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.5023(7)
_cell_length_b                   7.7274(4)
_cell_length_c                   22.8287(11)
_cell_measurement_reflns_used    9865
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      30.11
_cell_measurement_theta_min      2.78
_cell_volume                     2556.0(2)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 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 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100.00
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_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  0.0354
_diffrn_reflns_av_unetI/netI     0.0339
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            36255
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.000
_diffrn_reflns_theta_min         1.633
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.6872
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1323 before and 0.0572 after correction.
The Ratio of minimum to maximum transmission is 0.9212.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.122
_exptl_crystal_description       plate
_exptl_crystal_F_000             956
_exptl_crystal_size_max          0.858
_exptl_crystal_size_mid          0.283
_exptl_crystal_size_min          0.082
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.158
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details
;
 Flack x determined using 4697 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.2(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     623
_refine_ls_number_reflns         11120
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0370
_refine_ls_R_factor_gt           0.0354
_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^)+(0.0403P)^2^+0.5141P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0865
_refine_ls_wR_factor_ref         0.0874
_reflns_Friedel_coverage         0.860
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                10768
_reflns_number_total             11120
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d6ce00081a2.cif
_cod_data_source_block           dp171_0m
_cod_depositor_comments
'Adding full bibliography for 7251832--7251835.cif.'
_cod_original_sg_symbol_H-M      'P 21'
_cod_original_formula_sum        'C26 H47 O4.50'
_cod_database_code               7251835
_shelx_shelxl_version_number     2019/1
_shelx_estimated_absorpt_t_max   0.994
_shelx_estimated_absorpt_t_min   0.939
_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
 H3A-H6
 -2.3 with sigma of 0.02
3. Others
 Fixed Sof: C30D(0.5) H30A(0.5) H30B(0.5) H30C(0.5) C31C(0.5) H31A(0.5)
 H31B(0.5) H31C(0.5) C32C(0.5) H32A(0.5) H32B(0.5) H32C(0.5) C32D(0.5)
 H32D(0.5) H32E(0.5) H32F(0.5) C31D(0.5) H31D(0.5) H31E(0.5) H31F(0.5)
 C30C(0.5) H30D(0.5) H30E(0.5) H30F(0.5)
4.a Ternary CH refined with riding coordinates:
 C9B(H9B), C16B(H16B), C5B(H5B), C5A(H5A), C16A(H16A), C9A(H9A)
4.b Secondary CH2 refined with riding coordinates:
 C15B(H15A,H15B), C7B(H7BA,H7BB), C2B(H2BA,H2BB), C1B(H1BA,H1BB), C12B(H12A,
 H12B), C6B(H6BA,H6BB), C14A(H14C,H14D), C3B(H3BA,H3BB), C14B(H14A,H14B),
 C11B(H11A,H11B), C7A(H7AA,H7AB), C6A(H6AA,H6AB), C11A(H11C,H11D), C12A(H12C,
 H12D), C15A(H15C,H15D), C2A(H2AA,H2AB), C1A(H1AA,H1AB), C3A(H3AA,H3AB)
4.c Idealised Me refined as rotating group:
 C20B(H20A,H20B,H20C), C20A(H20D,H20E,H20F), C17B(H17A,H17B,H17C), C18B(H18A,
 H18B,H18C), C23(H23A,H23B,H23C), C27(H27A,H27B,H27C), C17A(H17D,H17E,H17F),
 C18A(H18D,H18E,H18F), C22(H22A,H22B,H22C), C28(H28A,H28B,H28C), C24(H24A,H24B,
 H24C), C26(H26A,H26B,H26C), C30D(H30A,H30B,H30C), C31C(H31A,H31B,H31C),
 C32C(H32A,H32B,H32C), C32D(H32D,H32E,H32F), C31D(H31D,H31E,H31F), C30C(H30D,
 H30E,H30F)
;
_shelx_res_checksum              74714
_olex2_submission_special_instructions 'No special instructions were received'