Peniphenone and Penilactone Formation in Penicillium crustosum via 1,4-Michael Additions of ortho-Quinone Methide from Hydroxyclavatol to γ-Butyrolactones from Crustosic Acid.
Fan, Jie; Liao, Ge; Kindinger, Florian; Ludwig-Radtke, Lena; Yin, Wen-Bing; Li, Shu-Ming; Journal of the American Chemical Society 141 (2019) 4225–4229; doi:10.1021/jacs.9b00110

data_4127501
_publ_section_title
;
 Peniphenone and Penilactone Formation in Penicillium crustosum via
 1,4-Michael Additions of ortho-Quinone Methide from Hydroxyclavatol to
 \g-Butyrolactones from Crustosic Acid.
;
_journal_issue                   10
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              4225
_journal_page_last               4229
_journal_paper_doi               10.1021/jacs.9b00110
_journal_volume                  141
_journal_year                    2019
_chemical_formula_sum            'C10 H12 O4'
_chemical_formula_weight         196.20
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/1
_cell_angle_alpha                77.750(5)
_cell_angle_beta                 69.610(4)
_cell_angle_gamma                66.847(5)
_cell_formula_units_Z            2
_cell_length_a                   7.7553(9)
_cell_length_b                   8.2119(10)
_cell_length_c                   8.3575(10)
_cell_measurement_temperature    113(2)
_cell_volume                     456.97(10)
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_diffrn_ambient_temperature      113(2)
_diffrn_measured_fraction_theta_full 0.926
_diffrn_measured_fraction_theta_max 0.926
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0585
_diffrn_reflns_av_unetI/netI     0.0557
_diffrn_reflns_Laue_measured_fraction_full 0.926
_diffrn_reflns_Laue_measured_fraction_max 0.926
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            3969
_diffrn_reflns_point_group_measured_fraction_full 0.926
_diffrn_reflns_point_group_measured_fraction_max 0.926
_diffrn_reflns_theta_full        64.115
_diffrn_reflns_theta_max         64.115
_diffrn_reflns_theta_min         5.669
_exptl_absorpt_coefficient_mu    0.929
_exptl_crystal_density_diffrn    1.426
_exptl_crystal_F_000             208
_exptl_crystal_size_max          0.900
_exptl_crystal_size_mid          0.500
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.391
_refine_diff_density_min         -0.328
_refine_diff_density_rms         0.085
_refine_ls_extinction_coef       0.044(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/1 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.589
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     134
_refine_ls_number_reflns         1409
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      1.589
_refine_ls_R_factor_all          0.0542
_refine_ls_R_factor_gt           0.0535
_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^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1801
_refine_ls_wR_factor_ref         0.1834
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1368
_reflns_number_total             1409
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b00110_si_002.cif
_cod_data_source_block           li28
_cod_database_code               4127501
_shelx_shelxl_version_number     2018/1
_shelx_estimated_absorpt_t_min   0.489
_shelx_estimated_absorpt_t_max   0.836
_shelx_res_checksum              91225
_shelx_hkl_checksum              52992