Nitric Oxide Inhibitory Meroterpenoids from the Fungus Penicillium purpurogenum MHZ 111.
Sun, Jing; Zhu, Zhi-Xiang; Song, Yue-Lin; Dong, Dan; Zheng, Jiao; Liu, Ting; Zhao, Yun-Fang; Ferreira, Daneel; Zjawiony, Jordan K.; Tu, Peng-Fei; Li, Jun; Journal of natural products 79 (2016) 1415–1422; doi:10.1021/acs.jnatprod.6b00160

data_1543150
_publ_section_title
;
 Nitric Oxide Inhibitory Meroterpenoids from the Fungus Penicillium
 purpurogenum MHZ 111.
;
_journal_issue                   5
_journal_name_full               'Journal of natural products'
_journal_page_first              1415
_journal_page_last               1422
_journal_paper_doi               10.1021/acs.jnatprod.6b00160
_journal_volume                  79
_journal_year                    2016
_chemical_formula_moiety         'C24 H28 O8, 2.78209(O)'
_chemical_formula_sum            'C24 H28 O10.79'
_chemical_formula_weight         489.12
_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'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2015-11-18
_audit_creation_method
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_cell_angle_alpha                90
_cell_angle_beta                 97.611(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   12.6572(4)
_cell_length_b                   6.67349(19)
_cell_length_c                   15.3170(5)
_cell_measurement_reflns_used    4738
_cell_measurement_temperature    103.3
_cell_measurement_theta_max      70.9938
_cell_measurement_theta_min      4.2603
_cell_volume                     1282.39(7)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution
'A short history of SHELX (Sheldrick, 2007)/Bruker'
_diffrn_ambient_temperature      103.3
_diffrn_detector_area_resol_mean 16.0971
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_details
;
  1 omega  -29.00   -2.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       -3.5000   88.0000    5.0000 27

  2 omega  -12.00   14.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       -3.5000  -88.0000  174.0000 26

  3 omega  -29.00   56.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.8122  -37.0000    0.0000 85

  4 omega   -4.00   68.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.8122  -88.0000  174.0000 72

  5 omega  -16.00   68.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.8122  -88.0000   -5.0000 84

  6 omega   53.00   79.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.8122   37.0000 -120.0000 26

  7 omega  -30.00   85.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.8122    0.0000   30.0000 115

  8 omega  -27.00   50.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.8122  -77.0000  -90.0000 77

  9 omega   56.00   83.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.8122   37.0000   90.0000 27

 10 omega   29.00   69.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.8122  -88.0000   68.0000 40

 11 omega   84.00  142.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -120.0000 58

 12 omega  126.00  162.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000   60.0000 36

 13 omega  109.00  149.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000 -120.0000 40

 14 omega   62.00  110.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -88.0000 -111.0000 48

 15 omega   84.00  175.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   30.0000 91

 16 omega   41.00   97.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -120.0000 56

 17 omega   49.00   88.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -30.0000 39

 18 omega   39.00  140.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -88.0000   -5.0000 101

 19 omega  134.00  173.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -150.0000 39

 20 omega  133.00  172.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      108.0000    0.0000 -150.0000 39

 21 omega   40.00   91.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -15.0000  -90.0000 51

 22 omega  117.00  143.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -15.0000  -90.0000 26

 23 omega   82.00  108.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -150.0000 26

 24 omega   40.00  106.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      108.0000    0.0000 -150.0000 66

 25 omega   41.00   72.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   90.0000 31

 26 omega   97.00  126.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000 -180.0000 29

 27 omega   62.00  117.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -130.0000 -155.0000 55
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.1019970000
_diffrn_orient_matrix_UB_12      -0.1244561000
_diffrn_orient_matrix_UB_13      0.0031448000
_diffrn_orient_matrix_UB_21      0.0666973000
_diffrn_orient_matrix_UB_22      -0.1670267000
_diffrn_orient_matrix_UB_23      0.0502766000
_diffrn_orient_matrix_UB_31      -0.0154345000
_diffrn_orient_matrix_UB_32      0.0997410000
_diffrn_orient_matrix_UB_33      0.0880204000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0197
_diffrn_reflns_av_unetI/netI     0.0295
_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       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8364
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.132
_diffrn_reflns_theta_min         4.264
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.851
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93501
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.267
_exptl_crystal_F_000             517
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.350
_refine_diff_density_max         1.327
_refine_diff_density_min         -0.390
_refine_diff_density_rms         0.080
_refine_ls_abs_structure_details
;
 Flack x determined using 1984 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     345
_refine_ls_number_reflns         4812
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0635
_refine_ls_R_factor_gt           0.0619
_refine_ls_shift/su_max          0.028
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1241P)^2^+0.5761P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1767
_refine_ls_wR_factor_ref         0.1790
_reflns_Friedel_coverage         0.808
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.950
_reflns_number_gt                4619
_reflns_number_total             4812
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np6b00160_si_003.cif
_cod_data_source_block           exp_3634
_cod_depositor_comments
'Adding full bibliography for 1543149--1543150.cif.'
_cod_original_cell_volume        1282.40(7)
_cod_database_code               1543150
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_shelx_estimated_absorpt_t_max   0.755
_shelx_estimated_absorpt_t_min   0.727
_shelx_hkl_checksum              56232
_shelx_res_checksum              66082
_shelx_shelxl_version_number     2014/7