Phomentrioloxin: A Phytotoxic Pentasubstituted Geranylcyclohexentriol Produced by Phomopsis sp., a Potential Mycoherbicide for Carthamus lanatus Biocontrol.
Cimmino, Alessio; Andolfi, Anna; Zonno, Maria C.; Troise, Ciro; Santini, Antonello; Tuzi, Angela; Vurro, Maurizio; Ash, Gavin; Evidente, Antonio; Journal of natural products 75 (2012) 1130–1137; doi:10.1021/np300200j

data_1507805
_publ_section_title
;
 Phomentrioloxin: A Phytotoxic Pentasubstituted Geranylcyclohexentriol
 Produced by Phomopsis sp., a Potential Mycoherbicide for Carthamus
 lanatus Biocontrol.
;
_journal_issue                   6
_journal_name_full               'Journal of natural products'
_journal_page_first              1130
_journal_page_last               1137
_journal_paper_doi               10.1021/np300200j
_journal_volume                  75
_journal_year                    2012
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C17 H24 O4'
_chemical_formula_sum            'C17 H24 O4'
_chemical_formula_weight         292.36
_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                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.632(3)
_cell_length_b                   11.982(7)
_cell_length_c                   29.48(2)
_cell_measurement_reflns_used    120
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      14.191
_cell_measurement_theta_min      2.764
_cell_volume                     1636.2(18)
_computing_cell_refinement       'Dirax/lsq (Duisenberg & Schreurs 1989-2000)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction        'EvalCCD (Duisenberg & Schreurs 1990-2000)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR97 (Altomare et al. 1999)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.940
_diffrn_measured_fraction_theta_max 0.940
_diffrn_measurement_device       '95mm CCD camera on \k-goniostat'
_diffrn_measurement_device_type  'Bruker-Nonius KappaCCD'
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0616
_diffrn_reflns_av_sigmaI/netI    0.0639
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            6405
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         3.25
_diffrn_source                   'Enraf Nonius FR590'
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.9983
_exptl_absorpt_correction_T_min  0.9518
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS(Bruker 2000)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.187
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.236
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details
;
the absolute structure parameter is meaningless because the 
compound is a weak anomalous scatterer. Merg 4 instruction
was used.
;
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     204
_refine_ls_number_reflns         1627
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.095
_refine_ls_R_factor_all          0.0897
_refine_ls_R_factor_gt           0.0546
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0342P)^2^+0.9314P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1037
_refine_ls_wR_factor_ref         0.1161
_reflns_number_gt                1182
_reflns_number_total             1627
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            np300200j_si_002.cif
_cod_data_source_block           phom
_cod_original_sg_symbol_H-M      'P 212121'
_cod_database_code               1507805