Four novel sesquiterpenoids with their anti-Alzheimer's disease activity from Nardostachys chinensis.
Wu, Pei-Qian; Yu, Yi-Fan; Zhao, Ye; Yu, Chun-Xue; Zhi, De-Juan; Qi, Feng-Ming; Fei, Dong-Qing; Zhang, Zhan-Xin; Organic & biomolecular chemistry 16 (2018) 9038–9045; doi:10.1039/c8ob02319k

data_7156562
_publ_section_title
;
 Four novel sesquiterpenoids with their anti-Alzheimer's disease activity
 from Nardostachys chinensis.
;
_journal_issue                   46
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              9038
_journal_page_last               9045
_journal_paper_doi               10.1039/c8ob02319k
_journal_volume                  16
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C15 H24 O3'
_chemical_formula_sum            'C15 H24 O3'
_chemical_formula_weight         252.34
_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'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2018-01-15
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2018-08-12 deposited with the CCDC.
2018-11-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.44121(16)
_cell_length_b                   11.19736(18)
_cell_length_c                   11.71740(18)
_cell_measurement_reflns_used    13586
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.6600
_cell_measurement_theta_min      4.2020
_cell_volume                     1369.93(4)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -82.00  39.00   1.00    1.00    --  -41.11  19.00 -90.00  121
  2  \w     23.00  97.00   1.00    1.00    --   41.11-125.00 120.00   74
  3  \w      1.00  82.00   1.00    1.00    --   41.11 -99.00 120.00   81
  4  \w     94.00 178.00   1.00    1.12    --  107.58 125.00 -30.00   84
  5  \w     34.00 122.00   1.00    1.12    --  107.58-125.00-150.00   88
  6  \w    101.00 178.00   1.00    1.12    --  107.58 107.00   1.00   77
  7  \w     94.00 178.00   1.00    1.12    --  107.58 125.00 150.00   84
  8  \w     31.00 136.00   1.00    1.12    --  107.58 -30.00 -30.00  105
  9  \w     78.00 178.00   1.00    1.12    --  107.58  61.00 150.00  100
 10  \w   -117.00  -9.00   1.00    1.00    --  -41.11 -77.00-120.00  108
 11  \w   -117.00  -9.00   1.00    1.00    --  -41.11 -77.00 120.00  108
 12  \w     78.00 178.00   1.00    1.12    --  107.58  61.00  90.00  100
 13  \w     78.00 178.00   1.00    1.12    --  107.58  61.00  30.00  100
 14  \w     75.00 178.00   1.00    1.12    --  107.58  77.00-120.00  103
 15  \w     79.00 178.00   1.00    1.12    --  107.58  30.00 -30.00   99
 16  \w    -69.00  16.00   1.00    1.00    --  -41.11  57.00   0.00   85
 17  \w   -117.00  -9.00   1.00    1.00    --  -41.11 -77.00   0.00  108
 18  \w   -113.00 -13.00   1.00    1.00    --  -41.23 -57.00 -90.00  100
 19  \w   -113.00 -13.00   1.00    1.00    --  -41.23 -57.00-180.00  100
 20  \w   -114.00 -11.00   1.00    1.00    --  -41.23 -66.00 143.00  103
 21  \w   -113.00 -13.00   1.00    1.00    --  -41.23 -57.00  30.00  100
 22  \w   -116.00 -17.00   1.00    1.00    --  -41.23 -38.00 120.00   99
 23  \w   -117.00  -9.00   1.00    1.00    --  -41.23 -77.00 -30.00  108
 24  \w     23.00  97.00   1.00    1.00    --   41.23-125.00-150.00   74
 25  \w     78.00 125.00   1.00    1.12    --  107.58  61.00  60.00   47
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0969505000
_diffrn_orient_matrix_UB_12      -0.0507500000
_diffrn_orient_matrix_UB_13      0.0864086000
_diffrn_orient_matrix_UB_21      0.1052060000
_diffrn_orient_matrix_UB_22      -0.0807384000
_diffrn_orient_matrix_UB_23      0.0505805000
_diffrn_orient_matrix_UB_31      0.0361156000
_diffrn_orient_matrix_UB_32      0.0991187000
_diffrn_orient_matrix_UB_33      0.0852581000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0350
_diffrn_reflns_av_unetI/netI     0.0198
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            17862
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.777
_diffrn_reflns_theta_min         5.465
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.665
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56480
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.223
_exptl_crystal_description       block
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.211
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details
;
 Flack x determined using 1109 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.07(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     168
_refine_ls_number_reflns         2733
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.095
_refine_ls_R_factor_all          0.0359
_refine_ls_R_factor_gt           0.0352
_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^)+(0.0632P)^2^+0.1309P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0925
_refine_ls_wR_factor_ref         0.0935
_reflns_Friedel_coverage         0.724
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.984
_reflns_number_gt                2673
_reflns_number_total             2733
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ob02319k2.cif
_cod_data_source_block           ncb-19
_cod_depositor_comments
'Adding full bibliography for 7156560--7156562.cif.'
_cod_database_code               7156562
_shelx_shelxl_version_number     2017/1
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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:
 C15(H15), C5(H5), C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C1(H1A,H1B), C6(H6A,H6B), C2(H2A,H2B)
2.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C12(H12A,H12B,H12C), C10(H10A,H10B,H10C), C14(H14A,H14B,
 H14C)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.581
_oxdiff_exptl_absorpt_empirical_full_min 0.646