Pseudoguaianelactones A-C: three unusual sesquiterpenoids from Lindera glauca with anti-inflammatory activities by inhibiting the LPS-induced expression of iNOS and COX-2.
Ruan, Qing-Feng; Jiang, Shi-Qin; Zheng, Xiao-Yun; Tang, Yu-Qian; Yang, Bao; Yi, Tao; Jin, Jing; Cui, Hui; Zhao, Zhongxiang; Chemical communications (Cambridge, England) 56 (2020) 1517–1520; doi:10.1039/c9cc09159a

data_7125699
_publ_section_title
;
 Pseudoguaianelactones A-C: three unusual sesquiterpenoids from Lindera
 glauca with anti-inflammatory activities by inhibiting the LPS-induced
 expression of iNOS and COX-2.
;
_journal_issue                   10
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              1517
_journal_page_last               1520
_journal_paper_doi               10.1039/c9cc09159a
_journal_volume                  56
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_compound_source        'Lindera glauca, Lindera, Lauraceae'
_chemical_formula_moiety         'C15 H22 O3'
_chemical_formula_sum            'C15 H22 O3'
_chemical_formula_weight         250.32
_chemical_melting_point          418.6(5)
_chemical_name_common            'Guaianelactone C'
_chemical_name_systematic
(4R,7S,7aS,10R,10aR)-10-hydroxy-7,10-dimethyl-3-methyleneoctahydro-4,10a-methanocyclopenta[b]oxonin-2(3H)-one
_chemical_properties_physical    Efflorescent
_space_group_crystal_system      tetragonal
_space_group_IT_number           92
_space_group_name_Hall           'P 4abw 2nw'
_space_group_name_H-M_alt        'P 41 21 2'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2018-11-23
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-08-04 deposited with the CCDC.	2019-12-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.72709(4)
_cell_length_b                   9.72709(4)
_cell_length_c                   28.60837(18)
_cell_measurement_reflns_used    25792
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      76.8010
_cell_measurement_theta_min      4.7790
_cell_volume                     2706.82(2)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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    -26.00  -1.00   0.50    0.05    --  -46.62  94.00-117.00   50
  2  \w     11.00  36.00   0.50    0.05    --   46.62 -38.00-114.00   50
  3  \w     52.00  77.00   0.50    0.05    --   46.62  38.00  40.00   50
  4  \w      7.00  32.00   0.50    0.05    --   46.62-100.00  37.00   50
  5  \w    -25.00  44.00   0.50    0.05    --   46.62 -94.00 131.00  138
  6  \w    -92.00 -67.00   0.50    0.10    -- -100.00  94.00-117.00   50
  7  \w   -151.00-126.00   0.50    0.10    -- -100.00 -94.00 131.00   50
  8  \w   -154.00-129.00   0.50    0.10    -- -100.00 -38.00-114.00   50
  9  \w    111.00 137.00   0.50    0.10    --  107.00  38.00  40.00   52
 10  \w     35.00  86.00   0.50    0.10    --  107.00 -94.00 131.00  102
 11  \w     77.00 108.00   0.50    0.10    --  107.00 -38.00-114.00   62
 12  \w    104.00 134.00   0.50    0.10    --  107.00 100.00 142.00   60
 13  \w    126.00 152.00   0.50    0.10    --  107.00  94.00-117.00   52
 14  \w     35.00  64.00   0.50    0.05    --   46.62  57.00 150.00   58
 15  \w     32.00 119.00   0.50    0.05    --   46.62  38.00 120.00  174
 16  \w     75.00 120.00   0.50    0.05    --   46.62  77.00-180.00   90
 17  \w     26.00  69.00   0.50    0.05    --   46.62  77.00-180.00   86
 18  \w   -104.00 -78.00   0.50    0.10    -- -100.00 -73.00 153.98   52
 19  \w   -111.00 -75.00   0.50    0.10    -- -100.00 -79.00 170.04   72
 20  \w   -104.00 -78.00   0.50    0.10    -- -100.00 -72.00 178.37   52
 21  \w   -154.00-128.00   0.50    0.10    -- -100.00 -77.00 150.00   52
 22  \w   -102.00 -76.00   0.50    0.10    -- -100.00 -77.00-180.00   52
 23  \w   -105.00 -79.00   0.50    0.10    -- -100.00 -77.00 150.00   52
 24  \w   -172.00 -81.00   0.50    0.10    -- -100.00 -65.00 122.13  182
 25  \w   -157.00-127.00   0.50    0.10    -- -100.00 -55.00 151.17   60
 26  \w   -164.00 -81.00   0.50    0.10    -- -100.00 -66.00 148.59  166
 27  \w   -103.00 -77.00   0.50    0.10    -- -100.00 -78.00 154.44   52
 28  \w   -167.00 -85.00   0.50    0.10    -- -100.00 -45.00   0.00  164
 29  \w   -154.00-122.00   0.50    0.10    -- -100.00 -77.00-180.00   64
 30  \w   -102.00 -76.00   0.50    0.10    -- -100.00 -77.00 120.00   52
 31  \w   -123.00 -87.00   0.50    0.10    -- -100.00 -55.00 151.17   72
 32  \w   -115.00 -80.00   0.50    0.10    -- -100.00 -70.00 135.90   70
 33  \w     36.00 121.00   0.50    0.10    --  107.00 -45.00  30.00  170
 34  \w     93.00 176.00   0.50    0.10    --  107.00  45.00 -90.00  166
 35  \w     34.00 109.00   0.50    0.10    --  107.00 -94.00 -30.00  150
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1460968000
_diffrn_orient_matrix_UB_12      0.0004073000
_diffrn_orient_matrix_UB_13      -0.0208342000
_diffrn_orient_matrix_UB_21      0.0185865000
_diffrn_orient_matrix_UB_22      0.1505538000
_diffrn_orient_matrix_UB_23      0.0154601000
_diffrn_orient_matrix_UB_31      0.0583392000
_diffrn_orient_matrix_UB_32      -0.0491144000
_diffrn_orient_matrix_UB_33      0.0471830000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0375
_diffrn_reflns_av_unetI/netI     0.0154
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            28910
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.071
_diffrn_reflns_theta_min         4.802
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.672
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58325
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.229
_exptl_crystal_description       tetragonal
_exptl_crystal_F_000             1088
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: ethyl acetate/methanol/water (9:1:0.5)'
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.179
_refine_diff_density_min         -0.155
_refine_diff_density_rms         0.030
_refine_ls_abs_structure_details
;
 Flack x determined using 1018 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         2656
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0266
_refine_ls_R_factor_gt           0.0261
_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^)+(0.0382P)^2^+0.4839P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0686
_refine_ls_wR_factor_ref         0.0690
_reflns_Friedel_coverage         0.636
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                2616
_reflns_number_total             2656
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc09159a2.cif
_cod_data_source_block           zzx_shj_181113
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '418.15-419.15' was changed
to '418.6(5)' -- the average value was taken and precision was
estimated.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 7125698--7125699.cif.
;
_cod_original_cell_volume        2706.82(3)
_cod_database_code               7125699
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.936
_shelx_estimated_absorpt_t_min   0.824
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_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:
 C007(H007), C008(H008), C00A(H00D)
2.b Secondary CH2 refined with riding coordinates:
 C00D(H00H,H00I), C00E(H00J,H00K), C00G(H00N,H00O), C00H(H00P,H00Q), C00I(H00R,
 H00S)
2.c Idealised Me refined as rotating group:
 C006(H00A,H00B,H00C), C00B(H00E,H00F,H00G)
2.d Idealised tetrahedral OH refined as rotating group:
 O003(H003)
;
_shelx_res_checksum              38033
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.473
_oxdiff_exptl_absorpt_empirical_full_min 0.723