Phytotoxic Eremophilane Sesquiterpenes from the Coprophilous Fungus Penicillium sp. G1-a14.
Del Valle, Paulina; Figueroa, Mario; Mata, Rachel; Journal of natural products 78 (2015) 339–342; doi:10.1021/np5009224

data_1518632
_publ_section_title
;
 Phytotoxic Eremophilane Sesquiterpenes from the Coprophilous Fungus
 Penicillium sp. G1-a14.
;
_journal_issue                   2
_journal_name_full               'Journal of natural products'
_journal_page_first              339
_journal_page_last               342
_journal_paper_doi               10.1021/np5009224
_journal_volume                  78
_journal_year                    2015
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C15 H22 O3'
_chemical_formula_sum            'C15 H22 O3'
_chemical_formula_weight         250.32
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.8914(2)
_cell_length_b                   10.9342(2)
_cell_length_c                   11.4227(2)
_cell_measurement_reflns_used    9023
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      68.25
_cell_measurement_theta_min      3.87
_cell_volume                     1360.32(4)
_computing_cell_refinement       'APEX2 V2014 (Bruker, 2012)'
_computing_data_collection       'APEX2 V2014 (Bruker, 2012)'
_computing_data_reduction        'SAINT V 827A (Bruker, 2012)'
_computing_molecular_graphics    'SHELXL-2013 (Sheldrick, 2013)'
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 0.83
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0459
_diffrn_reflns_av_unetI/netI     0.0153
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            27500
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.298
_diffrn_reflns_theta_min         5.601
_exptl_absorpt_coefficient_mu    0.669
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.222
_exptl_crystal_description       Prism
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.180
_refine_diff_density_max         0.151
_refine_diff_density_min         -0.118
_refine_diff_density_rms         0.029
_refine_ls_abs_structure_details
; 
 Flack x determined using 1032 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.02(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2481
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0331
_refine_ls_R_factor_gt           0.0329
_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^)+(0.0488P)^2^+0.2330P] 
 where P=(Fo^2^+2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0868
_refine_ls_wR_factor_ref         0.0870
_reflns_Friedel_coverage         0.725
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                2462
_reflns_number_total             2481
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np5009224_si_001.cif
_cod_data_source_block
404xyz14_(3R,6R-dihydroxy-9,7(11)-dien-8-oxoeremophilane)
_cod_depositor_comments          'Adding full bibliography for 1518632.cif.'
_cod_original_cell_volume        1360.31(4)
_cod_database_code               1518632
_shelx_estimated_absorpt_t_min   0.795
_shelx_estimated_absorpt_t_max   0.889
_shelxl_version_number           2013-2
_shelx_res_checksum              96822
_shelx_hkl_checksum              97185