Dihydro-β-agarofuran-Type Sesquiterpenoids from the Seeds of <i>Celastrus virens</i> and Their Multidrug Resistance Reversal Activity against the KB/VCR Cell Line.
Mu, Hongyan; Tang, Shuai; Zuo, Quan; Huang, Min; Zhao, Weimin; Journal of natural products 84 (2021) 588–600; doi:10.1021/acs.jnatprod.0c01182

data_1560946
_publ_section_title
;
 Dihydro-\b-agarofuran-Type Sesquiterpenoids from the Seeds of
 <i>Celastrus virens</i> and Their Multidrug Resistance Reversal Activity
 against the KB/VCR Cell Line.
;
_journal_issue                   3
_journal_name_full               'Journal of natural products'
_journal_page_first              588
_journal_page_last               600
_journal_paper_doi               10.1021/acs.jnatprod.0c01182
_journal_volume                  84
_journal_year                    2021
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C35 H40 O10'
_chemical_formula_sum            'C35 H40 O10'
_chemical_formula_weight         620.67
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-05-09
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.3224(5)
_cell_length_b                   17.2445(8)
_cell_length_c                   17.9240(8)
_cell_measurement_reflns_used    9787
_cell_measurement_temperature    150
_cell_measurement_theta_max      74.449
_cell_measurement_theta_min      4.672
_cell_volume                     3499.6(3)
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_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      150.0
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'D8 VENTURE'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0635
_diffrn_reflns_av_unetI/netI     0.0436
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            31324
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.632
_diffrn_reflns_theta_min         4.672
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.710
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_correction_T_min  0.6070
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1530 before and 0.0807 after correction. The Ratio of minimum to maximum transmission is 0.8053. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.178
_exptl_crystal_description       block
_exptl_crystal_F_000             1320
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_platon_squeeze_details
;
TITL cu_22020181_0m_a.res in P2(1)2(1)2(1)
CELL   11.3224   17.2445   17.9240     90.00     90.00     90.00
SPGR P212121
Q101 0.879 0.538 0.635 !       6.29 eA-3
C102 0.643 0.594 0.176 !       3.95 eA-3
C103 0.845 0.441 0.639 !       3.03 eA-3
C104 0.765 0.379 0.628 !       2.07 eA-3
C105 0.268 0.931 0.889 !       0.94 eA-3
Q106 0.829 0.652 0.101 !       0.50 eA-3
;
_refine_diff_density_max         0.935
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details
;
 Flack x determined using 2429 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     413
_refine_ls_number_reflns         7041
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0558
_refine_ls_R_factor_gt           0.0471
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0698P)^2^+0.7396P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1228
_refine_ls_wR_factor_ref         0.1314
_reflns_Friedel_coverage         0.788
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.978
_reflns_number_gt                6169
_reflns_number_total             7041
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np0c01182_si_002.cif
_cod_data_source_block           cu_22020181_0m_sq
_cod_depositor_comments          'Adding full bibliography for 1560946.cif.'
_cod_database_code               1560946
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.965
_shelx_estimated_absorpt_t_min   0.901
_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
2.a Ternary CH refined with riding coordinates:
 C1(H1), C9(H9), C6(H6A), C4(H4), C7(H7), C8(H8), C2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B)
2.c Aromatic/amide H refined with riding coordinates:
 C31(H31), C21(H21), C35(H35), C32(H32), C33(H33), C22(H22), C27(H27),
 C28(H28), C34(H34), C24(H24), C26(H26), C25(H25)
2.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C14(H14A,H14B,H14C), C12(H12A,H12B,H12C), C13(H13A,H13B,
 H13C), C19(H19A,H19B,H19C), C17(H17A,H17B,H17C)
2.e Idealised tetrahedral OH refined as rotating group:
 O6(H6)
;
_platon_squeeze_void_probe_radius 1.20
_olex2_submission_special_instructions 'No special instructions were received'