Indole Diterpenoids from an Endophytic Penicillium sp.
Ariantari, Ni P.; Ancheeva, Elena; Wang, Chenyin; Mándi, Attila; Knedel, Tim-O; Kurtán, Tibor; Chaidir, Chaidir; Müller, Werner E G; Kassack, Matthias U.; Janiak, Christoph; Daletos, Georgios; Proksch, Peter; Journal of natural products 82 (2019) 1412–1423; doi:10.1021/acs.jnatprod.8b00723

data_1552664
_publ_section_title
;
 Indole Diterpenoids from an Endophytic Penicillium sp.
;
_journal_issue                   6
_journal_name_full               'Journal of natural products'
_journal_page_first              1412
_journal_page_last               1423
_journal_paper_doi               10.1021/acs.jnatprod.8b00723
_journal_volume                  82
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C27 H27 N O3'
_chemical_formula_sum            'C27 H27 N O3'
_chemical_formula_weight         413.49
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                90
_cell_angle_beta                 94.4960(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.8611(5)
_cell_length_b                   7.1874(3)
_cell_length_c                   24.2244(10)
_cell_measurement_reflns_used    9907
_cell_measurement_temperature    140(2)
_cell_measurement_theta_max      65.7165
_cell_measurement_theta_min      3.6605
_cell_volume                     2058.79(15)
_computing_cell_refinement       'SAINT (Bruker, 2015)'
_computing_data_collection       'APEX2 (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2015)'
_computing_molecular_graphics    'DIAMOND 4.2.2 (Crystal Impact, 2016)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      140(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker Kappa APEX-II CCD area detector'
_diffrn_measurement_method       '\w scans, \f scans'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_radiation_source         'microfocus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0249
_diffrn_reflns_av_unetI/netI     0.0222
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            26702
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        65.649
_diffrn_reflns_theta_max         65.649
_diffrn_reflns_theta_min         1.829
_exptl_absorpt_coefficient_mu    0.686
_exptl_absorpt_correction_T_max  0.8642
_exptl_absorpt_correction_T_min  0.7720
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(<i>SADABS</i>; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.300
_refine_diff_density_max         0.170
_refine_diff_density_min         -0.143
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details
;
 Flack x determined using 3146 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(7)
_refine_ls_extinction_coef       0.0030(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     572
_refine_ls_number_reflns         7034
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0276
_refine_ls_R_factor_gt           0.0275
_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^)+(0.0483P)^2^+0.3328P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0752
_refine_ls_wR_factor_ref         0.0753
_reflns_Friedel_coverage         0.828
_reflns_Friedel_fraction_full    0.981
_reflns_Friedel_fraction_max     0.981
_reflns_number_gt                6992
_reflns_number_total             7034
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np8b00723_si_002.cif
_cod_data_source_block           cu_TOK_Proksch_AA102_2_0m_a
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1552664
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_min   0.821
_shelx_estimated_absorpt_t_max   0.821
_shelx_res_checksum              3058
_shelx_hkl_checksum              30012