Asperginols A and B, Diterpene Pyrones, from an <i>Aspergillus</i> sp. and the Structure Revision of Previously Reported Analogues.
Al-Khdhairawi, Amjad Ayad Qatran; Low, Yun-Yee; Manshoor, Nurhuda; Arya, Aditya; Jelecki, Maciej; Alshawsh, Mohammed Abdullah; Kamran, Sareh; Suliman, Rasha Saad; Low, Anis; Shivanagere Nagojappa, Narendra Babu; Weber, Jean-Frédéric F; Journal of natural products 83 (2020) 3564–3570; doi:10.1021/acs.jnatprod.0c00618

data_1559924
_publ_section_title
;
 Asperginols A and B, Diterpene Pyrones, from an <i>Aspergillus</i> sp.
 and the Structure Revision of Previously Reported Analogues.
;
_journal_issue                   12
_journal_name_full               'Journal of natural products'
_journal_page_first              3564
_journal_page_last               3570
_journal_paper_doi               10.1021/acs.jnatprod.0c00618
_journal_volume                  83
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C27 H40 O5'
_chemical_formula_sum            'C27 H40 O5'
_chemical_formula_weight         444.59
_chemical_melting_point          536.5(5)
_chemical_name_common            'Asperginol B'
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-08-29
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 110.001(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.4336(5)
_cell_length_b                   17.1372(6)
_cell_length_c                   17.1518(12)
_cell_measurement_reflns_used    10190
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      73.5750
_cell_measurement_theta_min      3.6760
_cell_volume                     3434.2(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'X-SEED (Barbour, 2001)'
_computing_publication_material  'enCIFer (Allen et al., 2004)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w    -63.00  28.00   1.00    1.00    --  -42.13  57.00 -60.00   91
  2  \w    -76.00 -19.00   1.00    1.00    --  -42.13 -38.00  60.00   57
  3  \w   -125.00  32.00   1.00    1.00    --  -42.13   0.00 -90.00  157
  4  \w     31.00  86.00   1.00    1.00    --   42.13-125.00-180.00   55
  5  \w     30.00 127.00   1.00    2.77    --  106.06 -77.00 -60.00   97
  6  \w     87.00 132.00   1.00    2.77    --  106.06 -30.00 -90.00   45
  7  \w    109.00 171.00   1.00    2.77    --  106.06  30.00 -30.00   62
  8  \w     92.00 175.00   1.00    2.77    --  106.06  77.00   0.00   83
  9  \w     87.00 174.00   1.00    2.77    --  106.06  61.00  60.00   87
 10  \w     82.00 130.00   1.00    2.77    --  106.06  45.00  60.00   48
 11  \w     79.00 178.00   1.00    2.77    --  106.06  30.00 120.00   99
 12  \w     49.00 101.00   1.00    2.77    --  106.06 -95.00 150.00   52
 13  \w     38.00 118.00   1.00    2.77    --  106.06-125.00 120.00   80
 14  \w     33.00 119.00   1.00    2.77    --  106.06-125.00 -60.00   86
 15  \w     40.00  65.00   1.00    2.77    --  106.06 -30.00 -90.00   25
 16  \w     24.00  80.00   1.00    2.77    --  106.06 -95.00-150.00   56
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scan'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0261
_diffrn_reflns_av_unetI/netI     0.0322
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            26254
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.196
_diffrn_reflns_theta_min         3.765
_exptl_absorpt_coefficient_mu    0.463
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.51309
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    0.860
_exptl_crystal_description       block
_exptl_crystal_F_000             968
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.157
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details
;
 Flack x determined using 4336 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.09(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.936
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     593
_refine_ls_number_reflns         13476
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.936
_refine_ls_R_factor_all          0.0615
_refine_ls_R_factor_gt           0.0527
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         <0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1232P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1495
_refine_ls_wR_factor_ref         0.1632
_reflns_Friedel_coverage         0.896
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.942
_reflns_number_gt                10826
_reflns_number_total             13476
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np0c00618_si_002.cif
_cod_data_source_block           Asperginol_B
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '536-537 K' was changed to
'536.5(5)' -- the average value was taken and precision was
estimated.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1559924
_shelx_shelxl_version_number     2018/3
_exptl_absorpt_special_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2), C6(H6), C10(H10), C14(H14), C2A(H2A), C6A(H6A), C10A(H10A), C14A(H14B)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C4(H4A,H4B), C5(H5A,H5B), C8(H8A,H8B), C9(H9A,H9B), C12(H12A,
 H12B), C13(H13A,H13B), C1A(H1AA,H1AB), C4A(H4AA,H4AB), C5A(H5AA,H5AB),
 C8A(H8AA,H8AB), C9A(H9AA,H9AB), C12A(H12C,H12D), C13A(H13C,H13D)
2.c X=CH2 refined with riding coordinates:
 C20(H20A,H20B), C20A(H20C,H20D)
2.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C19(H19A,H19B,
 H19C), C6"(H6"A,H6"B,H6"C), C7"(H7"A,H7"B,H7"C), C6'(H6'A,H6'B,H6'C), C7'(H7'A,
 H7'B,H7'C), C16A(H16D,H16E,H16F), C17A(H17D,H17E,H17F), C18A(H18D,H18E,H18F),
 C19A(H19D,H19E,H19F)
2.e Idealised tetrahedral OH refined as rotating group:
 O14(H14A), O3"(H3"), O3'(H3'), O14A(H14C)
;
_shelx_res_checksum              98028
_shelx_hkl_checksum              73105
_shelx_fab_checksum              76034
_olex2_submission_special_instructions 'No special instructions were received'