Cryptic Biosynthesis of the Berkeleypenostatins from Coculture of Extremophilic <i>Penicillium</i> sp.
Stierle, Andrea A.; Stierle, Donald B.; Decato, Daniel; Alverson, Jeremy; Apedaile, Lily; Journal of natural products 84 (2021) 1656–1665; doi:10.1021/acs.jnatprod.1c00248

data_1562423
_publ_section_title
;
 Cryptic Biosynthesis of the Berkeleypenostatins from Coculture of
 Extremophilic <i>Penicillium</i> sp.
;
_journal_issue                   5
_journal_name_full               'Journal of natural products'
_journal_page_first              1656
_journal_page_last               1665
_journal_paper_doi               10.1021/acs.jnatprod.1c00248
_journal_volume                  84
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C29 H42 O10'
_chemical_formula_sum            'C29 H42 O10'
_chemical_formula_weight         550.62
_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     dual
_audit_creation_date             2017-02-15
_audit_creation_method
;
Olex2 1.2
(compiled 2016.11.07 svn.r3352 for OlexSys, GUI svn.r5261)
;
_cell_angle_alpha                90
_cell_angle_beta                 98.1860(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.8533(6)
_cell_length_b                   7.0067(2)
_cell_length_c                   21.3135(7)
_cell_measurement_reflns_used    9986
_cell_measurement_temperature    100
_cell_measurement_theta_max      51.788
_cell_measurement_theta_min      2.368
_cell_volume                     2786.81(15)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100
_diffrn_detector                 'Bruker Photon-100 area detector'
_diffrn_detector_area_resol_mean 10.5
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'Fixed Chi Three-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Duo'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'Double Bounce Multilayer Mirror'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0369
_diffrn_reflns_av_unetI/netI     0.0327
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            30217
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        51.910
_diffrn_reflns_theta_max         51.909
_diffrn_reflns_theta_min         2.368
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\mus'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.814
_exptl_absorpt_correction_T_max  0.7502
_exptl_absorpt_correction_T_min  0.6949
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.0737 before and 0.0491 after correction.
The Ratio of minimum to maximum transmission is 0.9263.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_description       plate
_exptl_crystal_F_000             1184
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.402
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details
;
 Flack x determined using 2357 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     739
_refine_ls_number_reflns         6177
_refine_ls_number_restraints     34
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0410
_refine_ls_R_factor_gt           0.0342
_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^)+(0.0458P)^2^+0.9179P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0794
_refine_ls_wR_factor_ref         0.0831
_reflns_Friedel_coverage         0.807
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                5612
_reflns_number_total             6177
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np1c00248_si_002.cif
_cod_data_source_block           ds5
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 1562423.cif.
;
_cod_database_code               1562423
_shelx_estimated_absorpt_t_max   0.992
_shelx_estimated_absorpt_t_min   0.854
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid body (RIGU) restrains
 C15B, C17B, C16B, C18B, C19B, C20B, C21B
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3.a Ternary CH refined with riding coordinates:
 C1'(H1'), C2'(H2'A), C3'(H3'A), C4'(H4'A), C5'(H5'A), C5(H5), C7(H7), C8(H8),
 C12(H12), C1B'(H1B'), C2B'(H2BC), C3B'(H3BA), C4B'(H4BC), C5B'(H5BA), C5B(H5B),
  C7B(H7B), C8B(H8B), C12B(H12B)
3.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C4(H4A,H4B), C6(H6A,H6B), C6'(H6'A,H6'B), C15(H15A,H15B),
 C16(H16A,H16B), C17(H17A,H17B), C18(H18A,H18B), C19(H19A,H19B), C20(H20A,H20B),
  C2B(H2BA,H2BB), C4B(H4BA,H4BB), C6B(H6BA,H6BB), C6B'(H6BC,H6BD), C15B(H15C,
 H15D), C16B(H16C,H16D), C17B(H17C,H17D), C18B(H18C,H18D), C19B(H19C,H19D),
 C20B(H20C,H20D)
3.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C13(H13), C14(H14), C10B(H10B), C13B(H13B), C14B(H14B)
3.d Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C21B(H21D,H21E,H21F), C22B(H22D,
 H22E,H22F)
;
_shelx_res_checksum              43042
_shelx_hkl_checksum              83132
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'