Anthecularin: A Novel Sesquiterpene Lactone from Anthemis auriculata with Antiprotozoal Activity
Anastasia Karioti; Helen Skaltsa; Anthony Linden; Remo Perozzo; Reto Brun; Deniz Tasdemir; Journal of Organic Chemistry 72 (2007) 8103–8106; doi:10.1021/jo701751w

data_4023092
_publ_contact_author_address
; Institute of Organic Chemistry
   University of Z\"urich
   Winterthurerstrasse 190
   CH-8057 Z\"urich
   Switzerland
;
_publ_contact_author_email       alinden@oci.uzh.ch
_publ_contact_author_fax         '41 44 635 6812'
_publ_contact_author_name        'Dr. Anthony Linden'
_publ_contact_author_phone       '41 44 635 4228'
_publ_section_title
;
 Anthecularin: A Novel Sesquiterpene Lactone from
 Anthemis auriculata with Antiprotozoal Activity
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8103
_journal_page_last               8106
_journal_paper_doi               10.1021/jo701751w
_journal_volume                  72
_journal_year                    2007
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C15 H18 O3'
_chemical_formula_sum            'C15 H18 O3'
_chemical_formula_weight         246.30
_chemical_name_common            auricularin
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 92.6343(18)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.0010(2)
_cell_length_b                   12.2264(3)
_cell_length_c                   7.3355(2)
_cell_measurement_reflns_used    1508
_cell_measurement_temperature    160(1)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.0
_cell_volume                     627.23(3)
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 2000)'
_computing_data_reduction
'DENZO-SMN and SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  'SHELXL97 and PLATON (Spek, 2006)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      160(1)
_diffrn_detector                 '65 mm CCD camera on \k goniostat'
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Nonius KappaCCD area-detector diffractometer'
_diffrn_measurement_method       '\f and \w scans with \k offsets'
_diffrn_radiation_monochromator  'horizontally mounted graphite crystal'
_diffrn_radiation_source         'Nonius FR590 sealed tube generator'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0570
_diffrn_reflns_av_sigmaI/netI    0.0324
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            14891
_diffrn_reflns_theta_full        27.46
_diffrn_reflns_theta_max         27.46
_diffrn_reflns_theta_min         2.91
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.0895
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       tablet
_exptl_crystal_F_000             264
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.297
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.067
_refine_ls_abs_structure_details 'Friedel pairs merged'
_refine_ls_extinction_coef       0.46(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.123
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         1502
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.123
_refine_ls_R_factor_all          0.0468
_refine_ls_R_factor_gt           0.0432
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0648P)^2^+0.0324P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1002
_refine_ls_wR_factor_ref         0.1037
_reflns_number_gt                1403
_reflns_number_total             1503
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo701751w-File002.cif
_cod_data_source_block           RU0601
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4023092