Facile preparation of bioactive seco-guaianolides and guaianolides from Artemisia gorgonum and evaluation of their phytotoxicity.
Macías, Francisco A; Santana, Alejandro; Yamahata, Azusa; Varela, Rosa M.; Fronczek, Frank R.; Molinillo, José M G; Journal of natural products 75 (2012) 1967–1973; doi:10.1021/np300639b

data_1516053
_publ_section_title
;
 Facile preparation of bioactive seco-guaianolides and guaianolides from
 Artemisia gorgonum and evaluation of their phytotoxicity.
;
_journal_issue                   11
_journal_name_full               'Journal of natural products'
_journal_page_first              1967
_journal_page_last               1973
_journal_paper_doi               10.1021/np300639b
_journal_volume                  75
_journal_year                    2012
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C15 H18 O4, 0.2(C4 H8 O2)'
_chemical_formula_sum            'C15.8 H19.6 O4.4'
_chemical_formula_weight         279.91
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_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
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            20
_cell_length_a                   7.3918(2)
_cell_length_b                   29.7040(10)
_cell_length_c                   32.1937(10)
_cell_measurement_reflns_used    9658
_cell_measurement_temperature    90.0(5)
_cell_measurement_theta_max      68.1
_cell_measurement_theta_min      6.0
_cell_volume                     7068.6(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      90.0(5)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker Kappa APEX-II DUO'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'QUAZAR multilayer optics'
_diffrn_radiation_source         'I\mS microfocus'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0318
_diffrn_reflns_av_sigmaI/netI    0.0236
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            57945
_diffrn_reflns_theta_full        67.00
_diffrn_reflns_theta_max         68.4
_diffrn_reflns_theta_min         2.9
_exptl_absorpt_coefficient_mu    0.784
_exptl_absorpt_correction_T_max  0.877
_exptl_absorpt_correction_T_min  0.793
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2004)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'needle fragment'
_exptl_crystal_F_000             2992
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.298
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details '5549 Friedel pairs, (Flack, 1983)'
_refine_ls_abs_structure_Flack   0.00(7)
_refine_ls_extinction_coef       0.00010(3)
_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   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     929
_refine_ls_number_reflns         12751
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0291
_refine_ls_R_factor_gt           0.0287
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0457P)^2^+1.5955P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0769
_refine_ls_wR_factor_ref         0.0772
_reflns_number_gt                12553
_reflns_number_total             12751
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            np300639b_si_002.cif
_cod_data_source_block           ASF-Epox-IFS
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/usr/data/users/saulius/automatic-downloads/retrospective/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_sg_symbol_H-M      'P 21 21 21 '
_cod_original_formula_sum        'C15.80 H19.60 O4.40'
_cod_database_code               1516053