Insights into isostructural and non-isostructural crystals of esters of oleanolic acid and its 11-oxo derivatives
Langer, Dominik; Wicher, Barbara; Bendzinska-Berus, Wioletta; Bednarczyk-Cwynar, Barbara; Tykarska, Ewa; Acta Crystallographica Section B 78 (2022) –; doi:10.1107/S2052520622005972

data_2109011
_publ_section_title
;
 Insights into isostructural and non-isostructural crystals of esters of
 oleanolic acid and its 11-oxo derivatives
;
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2052520622005972
_journal_volume                  78
_journal_year                    2022
_chemical_absolute_configuration syn
_chemical_formula_moiety         '0.29(C32 H52 O4), 0.71(C32 H50 O4)'
_chemical_formula_sum            'C32 H50.57 O4'
_chemical_formula_weight         499.29
_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
_audit_creation_date             2020-03-04
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                92.5990(10)
_cell_angle_beta                 94.416(2)
_cell_angle_gamma                98.623(2)
_cell_formula_units_Z            2
_cell_length_a                   7.1965(2)
_cell_length_b                   13.3283(2)
_cell_length_c                   15.0866(3)
_cell_measurement_reflns_used    32558
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      76.252
_cell_measurement_theta_min      2.898
_cell_volume                     1424.08(5)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_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    'SIR2004 (Burla et al., 2005)'
_diffrn_ambient_temperature      130.15
_diffrn_detector_area_resol_mean 10.3991
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0257
_diffrn_reflns_av_unetI/netI     0.0159
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            51114
_diffrn_reflns_point_group_measured_fraction_full 0.963
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        66.590
_diffrn_reflns_theta_max         66.590
_diffrn_reflns_theta_min         4.594
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.579
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.164
_exptl_crystal_description       block
_exptl_crystal_F_000             549
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.564
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details
;
 Flack x determined using 4528 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(5)
_refine_ls_extinction_coef       0.0021(5)
_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   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     695
_refine_ls_number_reflns         9718
_refine_ls_number_restraints     13
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0397
_refine_ls_R_factor_gt           0.0390
_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^)+(0.0517P)^2^+0.5519P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1001
_refine_ls_wR_factor_ref         0.1008
_reflns_Friedel_coverage         0.928
_reflns_Friedel_fraction_full    0.927
_reflns_Friedel_fraction_max     0.927
_reflns_number_gt                9571
_reflns_number_total             9718
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            rm5063sup1.cif
_cod_data_source_block           2a_11-oxo-ethyl-OA
_cod_database_code               2109011
_publcif_datablock.id            {1bf8148a-8718-4794-92cf-ab9cbfdcb4c6}
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.944
_shelx_estimated_absorpt_t_min   0.893
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All O(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C17A-C28A = C17A-C28C = C31A-C32A = C31C-C32C
 1.5 with sigma of 0.01
 C28A-O29A = C28C-O29C
 1.38 with sigma of 0.01
 O29A-C31A = O29C-C31C
 1.45 with sigma of 0.01
 C28A-O28A = C28C-O28C
 1.2 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(C28A) = Uanis(C28C)
Uanis(O29A) = Uanis(O29C)
Uanis(C31A) = Uanis(C31C)
Uanis(C32A) = Uanis(C32C)
Uanis(O28A) = Uanis(O28C)
Uanis(C13A) = Uanis(C13C)
4. Others
 Sof(H11A)=Sof(H11B)=Sof(C13C)=Sof(H13C)=Sof(H18B)=Sof(C28A)=Sof(C31A)=
 Sof(H31A)=Sof(H31B)=Sof(C32A)=Sof(H32A)=Sof(H32B)=Sof(H32C)=Sof(O12A)=
 Sof(O28A)=Sof(O29A)=1-FVAR(1)
 Sof(H12A)=Sof(C13A)=Sof(H18A)=Sof(O11A)=Sof(C28C)=Sof(O29C)=Sof(C31C)=
 Sof(H31C)=Sof(H31D)=Sof(O28C)=Sof(C32C)=Sof(H32D)=Sof(H32E)=Sof(H32F)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C3A(H3A), C5A(H5A), C9A(H9A), C13C(H13C), C18A(H18A), C18A(H18B), C3B(H3B),
 C5B(H5B), C9B(H9B), C18B(H18C)
5.b Secondary CH2 refined with riding coordinates:
 C1A(H1AA,H1AB), C2A(H2AA,H2AB), C6A(H6AA,H6AB), C7A(H7AA,H7AB), C11A(H11A,
 H11B), C15A(H15A,H15B), C16A(H16A,H16B), C19A(H19A,H19B), C21A(H21A,H21B),
 C22A(H22A,H22B), C31A(H31A,H31B), C31C(H31C,H31D), C1B(H1BA,H1BB), C2B(H2BA,
 H2BB), C6B(H6BA,H6BB), C7B(H7BA,H7BB), C15B(H15C,H15D), C16B(H16C,H16D),
 C19B(H19C,H19D), C21B(H21C,H21D), C22B(H22C,H22D), C31B(H31E,H31F)
5.c Aromatic/amide H refined with riding coordinates:
 C12A(H12A), C12B(H12B)
5.d Tetrahedral OH refined with riding coordinates:
 O3A(H3AA), O3B(H3BA)
5.e Idealised Me refined as rotating group:
 C23A(H23A,H23B,H23C), C24A(H24A,H24B,H24C), C25A(H25A,H25B,H25C), C26A(H26A,
 H26B,H26C), C27A(H27A,H27B,H27C), C29A(H29A,H29B,H29C), C30A(H30A,H30B,H30C),
 C32A(H32A,H32B,H32C), C32C(H32D,H32E,H32F), C23B(H23D,H23E,H23F), C24B(H24D,
 H24E,H24F), C25B(H25D,H25E,H25F), C26B(H26D,H26E,H26F), C27B(H27D,H27E,H27F),
 C29B(H29D,H29E,H29F), C30B(H30D,H30E,H30F), C32B(H32G,H32H,H32I)
;
_shelx_res_checksum              338
_shelx_hkl_checksum              72752
_olex2_submission_special_instructions 'No special instructions were received'
_cod_database_fobs_code 2109011