Parnapimarol and nepetaparnone from Nepeta parnassica.
Gkinis, Giorgos; Ioannou, Efstathia; Quesada, Antonio; Vagias, Constantinos; Tzakou, Olga; Roussis, Vassilios; Journal of natural products 71 (2008) 926–928; doi:10.1021/np800043b

data_1504455
_publ_section_title
;
 Parnapimarol and nepetaparnone from Nepeta parnassica.
;
_journal_issue                   5
_journal_name_full               'Journal of natural products'
_journal_page_first              926
_journal_page_last               928
_journal_paper_doi               10.1021/np800043b
_journal_volume                  71
_journal_year                    2008
_chemical_compound_source
;
'natural product isolated from Nepeta parnassica'
;
_chemical_formula_moiety         'C20 H24 O4'
_chemical_formula_sum            'C20 H24 O4'
_chemical_formula_weight         328.39
_chemical_name_common
;
none
;
_chemical_name_systematic
;
(1R,2R,3R,8S,9S,10S)-3,7,10,14-tetramethyl-15,17-dioxapentacyclo
[7.5.2.2^2,8^.0^2,6^.0^9,13^]octadeca-6,13-diene-16,18-dione
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2007-09-11T12:51:54-00:00
_audit_creation_method           'from SHELXL-97 with WinGX routine CIF_UPDATE'
_audit_update_record
;
november 9, 2007 assembled
;
_cell_angle_alpha                90
_cell_angle_beta                 102.65(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.215(4)
_cell_length_b                   12.6695(12)
_cell_length_c                   13.163(2)
_cell_measurement_reflns_used    40
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.02
_cell_measurement_wavelength     0.71073
_cell_volume                     1662.2(8)
_computing_cell_refinement       'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)'
_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_data_reduction        'EvalCCD (Duisenberg & Schreurs 1990-2000)'
_computing_molecular_graphics    'Platon for Windows , (Speck, 2006)'
_computing_publication_material
;
WinGX publication routines (Farrugia, 1999), EnCIFer v 1.2 (CCDC, 2005)'
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       '95mm CCD camera on \k-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       CCD
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0836
_diffrn_reflns_av_unetI/netI     0.0455
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            39115
_diffrn_reflns_theta_full        25
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         3.17
_exptl_absorpt_coefficient_mu    0.09
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_correction_T_min  0.980
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2.10 (Sheldrick, G.M. 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_preparation
;
Crystals suitable for x-ray diffraction were obtained by slow 
evaporation from diethyl ether
;
_exptl_crystal_size_max          0.63
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.404
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3814
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0998
_refine_ls_R_factor_gt           0.0598
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0629P)^2^+1.2874P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1373
_refine_ls_wR_factor_ref         0.1596
_reflns_number_gt                2532
_reflns_number_total             3814
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            np800043b-file001.cif
_cod_data_source_block           TZN
_cod_original_sg_symbol_Hall     '-p 2ybc'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1504455