Cyperane-Type and Related (Nor)Sesquiterpenoids from the Root Bark of Acanthopanax gracilistylus and Their Inhibitory Effects on Nitric Oxide Production
Xu, Hong-Bo; Yang, Tong-Hua; Xie, Pei; Tang, Zhi-Shu; Xu, Huai-Li; Deng, Chong; Liang, Yan-Ni; Zhou, Rui; Liu, Shi-Jun; Zhang, Yu; Journal of Natural Products  (2020) –; doi:10.1021/acs.jnatprod.9b00913

data_1557853
_publ_section_title
;
 Cyperane-Type and Related (Nor)Sesquiterpenoids from the Root Bark of
 Acanthopanax gracilistylus and Their Inhibitory Effects on Nitric Oxide
 Production
;
_journal_name_full               'Journal of Natural Products'
_journal_paper_doi               10.1021/acs.jnatprod.9b00913
_journal_year                    2020
_chemical_formula_moiety         'C15 H24 O4'
_chemical_formula_sum            'C15 H24 O4'
_chemical_formula_weight         268.34
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-02-07
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                82.846(3)
_cell_angle_beta                 86.058(3)
_cell_angle_gamma                88.035(3)
_cell_formula_units_Z            2
_cell_length_a                   8.5031(11)
_cell_length_b                   8.6453(11)
_cell_length_c                   9.5875(13)
_cell_measurement_reflns_used    9343
_cell_measurement_temperature    153
_cell_measurement_theta_max      68.338
_cell_measurement_theta_min      4.658
_cell_volume                     697.42(16)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      153.02
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0589
_diffrn_reflns_av_unetI/netI     0.0407
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            26540
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.677
_diffrn_reflns_theta_min         4.658
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.740
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6632
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1162 before and 0.0731 after correction. The Ratio of minimum to maximum transmission is 0.8806. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_description       block
_exptl_crystal_F_000             292
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.319
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       0.027(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.173
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     179
_refine_ls_number_reflns         2535
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.173
_refine_ls_R_factor_all          0.0654
_refine_ls_R_factor_gt           0.0418
_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^)+(0.0575P)^2^+0.2349P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1122
_refine_ls_wR_factor_ref         0.1205
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2236
_reflns_number_total             2535
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np9b00913_si_002.cif
_cod_data_source_block           s
_cod_database_code               1557853
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.809
_shelx_estimated_absorpt_t_min   0.709
_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:
 C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C11(H11A,H11B), C8(H8A,H8B), C9(H9A,H9B), C2(H2A,H2B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C12(H12A,H12B,H12C), C13(H13A,H13B,H13C)
2.e Idealised tetrahedral OH refined as rotating group:
 O4(H4), O2(H2), O3(H3)
;
_shelx_res_checksum              34661
_shelx_hkl_checksum              42454
_olex2_submission_special_instructions 'No special instructions were received'