Stewartiacids A–N, C-23 carboxylated triterpenoids from Chinese Stewartia and their inhibitory effects against ATP-citrate lyase and NF-κB
Wan, Jiang; Zang, Yi; Xiao, Dao-An; Li, Na; Li, Junmin; Jin, Ze-Xin; Chen, De-Lei; Xiong, Juan; Li, Jia; Hu, Jin-Feng; RSC Advances 10 (2020) 3343–3356; doi:10.1039/C9RA09542J

data_7239808
_publ_section_title
;
 Stewartiacids A--N, C-23 carboxylated triterpenoids from Chinese
 Stewartia and their inhibitory effects against ATP-citrate lyase and
 NF-\kB
;
_journal_issue                   6
_journal_name_full               'RSC Advances'
_journal_page_first              3343
_journal_page_last               3356
_journal_paper_doi               10.1039/C9RA09542J
_journal_volume                  10
_journal_year                    2020
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C31 H50 O6, H2 O'
_chemical_formula_sum            'C31 H52 O7'
_chemical_formula_weight         536.72
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2018-06-22
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-10-14 deposited with the CCDC.	2020-01-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.9170(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   30.9220(6)
_cell_length_b                   13.9294(3)
_cell_length_c                   14.7361(3)
_cell_measurement_reflns_used    9959
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      54.873
_cell_measurement_theta_min      3.05
_cell_volume                     6039.4(2)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      169.98
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0507
_diffrn_reflns_av_unetI/netI     0.0382
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            48612
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         55.014
_diffrn_reflns_theta_min         3.054
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.421
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.5610
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1510 before and 0.0691 after correction. The Ratio of minimum to maximum transmission is 0.7472. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.181
_exptl_crystal_description       plate
_exptl_crystal_F_000             2352
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.02
_refine_diff_density_max         1.152
_refine_diff_density_min         -0.472
_refine_diff_density_rms         0.076
_refine_ls_abs_structure_details
;
 Flack x determined using 3901 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.10(8)
_refine_ls_extinction_coef       0.0029(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     710
_refine_ls_number_reflns         11459
_refine_ls_number_restraints     13
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0955
_refine_ls_R_factor_gt           0.0875
_refine_ls_shift/su_max          0.016
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1857P)^2^+5.4337P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2556
_refine_ls_wR_factor_ref         0.2669
_reflns_Friedel_coverage         0.915
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.993
_reflns_number_gt                9888
_reflns_number_total             11459
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ra09542j2.cif
_cod_data_source_block           mjl18275_0m
_cod_depositor_comments
'Adding full bibliography for 7239805--7239808.cif.'
_cod_database_code               7239808
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.992
_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, All O(H) groups, All O(H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(O1S) \\sim Ueq, Uanis(O2S) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
3.a Riding coordinates:
 O1S(H1SA,H1SB), O2S(H2SA,H2SB)
3.b Ternary CH refined with riding coordinates:
 C3(H3A), C5(H5A), C9(H9), C11(H11), C18(H18), C19(H19), C20(H20), C22(H22),
 C3A(H3AB), C5A(H5AB), C9A(H9A), C11A(H11A), C18A(H18A), C19A(H19A), C20A(H20A),
  C22A(H22A)
3.c Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C6(H6A,H6B), C7(H7A,H7B), C15(H15A,H15B), C16(H16A,
 H16B), C21(H21A,H21B), C1A(H1AB,H1AC), C2A(H2AA,H2AB), C6A(H6AB,H6AC),
 C7A(H7AA,H7AB), C15A(H15C,H15D), C16A(H16C,H16D), C21A(H21C,H21D)
3.d Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C25(H25A,H25B,H25C), C26(H26A,H26B,H26C), C27(H27A,H27B,
 H27C), C28(H28A,H28B,H28C), C29(H29A,H29B,H29C), C30(H30A,H30B,H30C), C31(H31A,
 H31B,H31C), C24A(H24D,H24E,H24F), C25A(H25D,H25E,H25F), C26A(H26D,H26E,H26F),
 C27A(H27D,H27E,H27F), C28A(H28D,H28E,H28F), C29A(H29D,H29E,H29F), C30A(H30D,
 H30E,H30F), C31A(H31D,H31E,H31F)
3.e Idealised tetrahedral OH refined as rotating group:
 O1(H1), O3(H3), O5(H5), O6(H6), O1A(H1AA), O3A(H3AA), O5A(H5AA), O6A(H6AA)
;
_shelx_res_checksum              19059
_olex2_submission_special_instructions 'No special instructions were received'