Peniisocoumarins A-J: Isocoumarins from Penicillium commune QQF-3, an Endophytic Fungus of the Mangrove Plant Kandelia candel.
Cai, Runlin; Wu, Yingnan; Chen, Senhua; Cui, Hui; Liu, Zhaoming; Li, Chunyuan; She, Zhigang; Journal of natural products 81 (2018) 1376–1383; doi:10.1021/acs.jnatprod.7b01018

data_1553332
_publ_section_title
;
 Peniisocoumarins A-J: Isocoumarins from Penicillium commune QQF-3, an
 Endophytic Fungus of the Mangrove Plant Kandelia candel.
;
_journal_issue                   6
_journal_name_full               'Journal of natural products'
_journal_page_first              1376
_journal_page_last               1383
_journal_paper_doi               10.1021/acs.jnatprod.7b01018
_journal_volume                  81
_journal_year                    2018
_chemical_formula_moiety         'C28 H24 O12'
_chemical_formula_sum            'C28 H24 O12'
_chemical_formula_weight         504.44
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2017-10-13
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                90
_cell_angle_beta                 118.274(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   27.9933(4)
_cell_length_b                   9.57267(8)
_cell_length_c                   22.8556(4)
_cell_measurement_reflns_used    13275
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      73.9060
_cell_measurement_theta_min      4.3760
_cell_volume                     5393.91(16)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2913
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.987
_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    -59.00  29.00   1.00    1.00    --  -41.95  59.00 -91.00   88
  2  \w    -77.00 -51.00   1.00    1.00    --  -41.95 -37.00 -30.00   26
  3  \w    -94.00 -18.00   1.00    1.00    --  -41.95 -37.00   0.00   76
  4  \w     24.00  82.00   1.00    1.00    --   41.95-125.00  60.00   58
  5  \w     37.00 118.00   1.00    3.98    --  107.79-125.00  30.00   81
  6  \w     54.00  97.00   1.00    3.98    --  107.79 -30.00  30.00   43
  7  \w     81.00 162.00   1.00    3.98    --  107.79  30.00  90.00   81
  8  \w    143.00 178.00   1.00    3.98    --  107.79  61.00  30.00   35
  9  \w    132.00 157.00   1.00    3.98    --  107.79 125.00 120.00   25
 10  \w     82.00 175.00   1.00    3.98    --  107.79  45.00 150.00   93
 11  \w     84.00 110.00   1.00    3.98    --  107.79  61.00 -30.00   26
 12  \w     84.00 178.00   1.00    3.98    --  107.79  45.00 -30.00   94
 13  \w     79.00 104.00   1.00    3.98    --  107.79  61.00   0.00   25
 14  \w     83.00 108.00   1.00    3.98    --  107.79  45.00  30.00   25
 15  \w     80.00 113.00   1.00    3.98    --  107.79  61.00  30.00   33
 16  \w     75.00 178.00   1.00    3.98    --  107.79  77.00   0.00  103
 17  \w     75.00 101.00   1.00    3.98    --  107.79  77.00 -30.00   26
 18  \w     36.00  87.00   1.00    3.98    --  107.79 -45.00-120.00   51
 19  \w     79.00 129.00   1.00    3.98    --  107.79 -77.00-180.00   50
 20  \w     60.00  87.00   1.00    1.00    --   41.95-125.00-180.00   27
 21  \w     25.00 108.00   1.00    3.98    --  107.79 -94.00-180.00   83
 22  \w     47.00  73.00   1.00    3.98    --  107.79 -77.00-180.00   26
 23  \w   -114.00 -16.00   1.00    1.00    --  -41.95 -59.00 128.00   98
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0417449000
_diffrn_orient_matrix_UB_12      0.1063646000
_diffrn_orient_matrix_UB_13      -0.0472768000
_diffrn_orient_matrix_UB_21      -0.0162892000
_diffrn_orient_matrix_UB_22      0.0357038000
_diffrn_orient_matrix_UB_23      0.0538511000
_diffrn_orient_matrix_UB_31      0.0435269000
_diffrn_orient_matrix_UB_32      0.1154796000
_diffrn_orient_matrix_UB_33      0.0269629000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0203
_diffrn_reflns_av_unetI/netI     0.0160
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            20550
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.104
_diffrn_reflns_theta_min         3.586
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.097
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71746
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.340
_exptl_crystal_description       prism
_exptl_crystal_F_000             2250
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.229
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     367
_refine_ls_number_reflns         5408
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0402
_refine_ls_R_factor_gt           0.0384
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0540P)^2^+3.8683P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1061
_refine_ls_wR_factor_ref         0.1079
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5104
_reflns_number_total             5408
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np7b01018_si_002.cif
_cod_data_source_block           17032701
_cod_depositor_comments
;

2025-06-17
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C H O'
_cod_original_formula_weight         29.02
_cod_original_formula_moiety         '0.05(C28 H24 O12)'
_cod_original_formula_units_Z            150
_cod_original_cell_volume        5393.89(16)
_cod_database_code               1553332
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C H O '
_chemical_oxdiff_usercomment     Q-6
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Rigid bond restraints
 O10, C25
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.001
3.a Ternary CH refined with riding coordinates:
 C21(H21), C24(H24), C26(H26), C27(H27)
3.b Aromatic/amide H refined with riding coordinates:
 C16(H16), C20(H20), C29(H29), C33(H33), C36(H36), C39(H39)
3.c Idealised Me refined as rotating group:
 C35(H35A,H35B,H35C), C37(H37A,H37B,H37C), C40(H40A,H40B,H40C), C41(H41A,H41B,
 H41C)
3.d Idealised tetrahedral OH refined as rotating group:
 O2(H2), O12(H12)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.587
_oxdiff_exptl_absorpt_empirical_full_min 0.835