Neuroprotective azaphilones from a deep-sea derived fungus <i>Penicillium</i> sp. SCSIO41030.
Chen, Weihao; Jiang, Jiahui; Pang, Xiaoyan; Song, Yingying; Yang, Zhiyou; Wang, Junfeng; Liu, Yonghong; Organic & biomolecular chemistry 22 (2024) 4521–4527; doi:10.1039/d4ob00586d

data_7159943
_publ_section_title
;
 Neuroprotective azaphilones from a deep-sea derived fungus
 <i>Penicillium</i> sp. SCSIO41030.
;
_journal_issue                   22
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4521
_journal_page_last               4527
_journal_paper_doi               10.1039/d4ob00586d
_journal_volume                  22
_journal_year                    2024
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C17 H22 O4'
_chemical_formula_sum            'C17 H22 O4'
_chemical_formula_weight         290.34
_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_block_doi                 10.5517/ccdc.csd.cc2d9yth
_audit_creation_date             2021-03-31
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2022-10-20 deposited with the CCDC.	2024-05-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.781(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.6306(2)
_cell_length_b                   22.6115(8)
_cell_length_c                   12.1140(5)
_cell_measurement_reflns_used    6171
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.9520
_cell_measurement_theta_min      3.9460
_cell_volume                     1538.95(10)
_computing_cell_refinement       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Pilatus3R 200K-A'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.982
_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    -45.00  29.00   0.50    1.00    --    0.00 -77.00 150.00  148
  2  \w    -12.00  13.00   0.50    1.00    --    0.00  38.00 -90.00   50
  3  \w     31.00  87.00   0.50    1.00    --    0.00  38.00 -90.00  112
  4  \w      2.00  30.00   0.50    1.00    --    0.00 -82.00  90.00   56
  5  \w     32.00  86.00   0.50    1.00    --    0.00  38.00 -30.00  108
  6  \w    -33.00   7.00   0.50    1.00    --    0.00 -82.00 -90.00   80
  7  \w     73.00 124.00   0.50    8.00    --   95.80  61.00 -60.00  102
  8  \w     80.00 183.00   0.50    8.00    --   95.80  45.00-180.00  206
  9  \w     19.00 103.00   0.50    8.00    --   95.80 -77.00 150.00  168
 10  \w     10.00  48.00   0.50    8.00    --   95.80 -30.00-120.00   76
 11  \w     59.00 111.00   0.50    8.00    --   95.80 -30.00-120.00  104
 12  \w     37.00 118.00   0.50    8.00    --   95.80 -61.00 -30.00  162
 13  \w    105.00 183.00   0.50    8.00    --   95.80  77.00 -60.00  156
 14  \w     58.00  94.00   0.50    8.00    --   95.80 -77.00 -30.00   72
 15  \w     69.00 106.00   0.50    8.00    --   95.80 -30.00 150.00   74
 16  \w     87.00 173.00   0.50    8.00    --   95.80  30.00 150.00  172
 17  \w      8.00 115.00   0.50    8.00    --   95.80 -61.00-150.00  214
 18  \w     59.00 105.00   0.50    8.00    --   95.80 -77.00-120.00   92
 19  \w      8.00  35.00   0.50    8.00    --   95.80 -77.00 -30.00   54
 20  \w     73.00 132.00   0.50    8.00    --   95.80  61.00 -30.00  118
 21  \w    157.00 184.00   0.50    8.00    --   95.80  61.00 -30.00   54
 22  \w     90.00 115.00   0.50    8.00    --   95.80  82.00  60.00   50
 23  \w    136.00 161.00   0.50    8.00    --   95.80  82.00  60.00   50
 24  \w    120.00 178.00   0.50    8.00    --   95.80   0.00 120.00  116
 25  \w     26.00  63.00   0.50    8.00    --   95.80   0.00 120.00   74
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro: Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0438456000
_diffrn_orient_matrix_UB_12      0.0408944000
_diffrn_orient_matrix_UB_13      0.0982798000
_diffrn_orient_matrix_UB_21      -0.1766490000
_diffrn_orient_matrix_UB_22      -0.0453711000
_diffrn_orient_matrix_UB_23      0.0426801000
_diffrn_orient_matrix_UB_31      0.2049934000
_diffrn_orient_matrix_UB_32      -0.0302053000
_diffrn_orient_matrix_UB_33      0.0690367000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0600
_diffrn_reflns_av_unetI/netI     0.0584
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            15141
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.349
_diffrn_reflns_theta_min         3.657
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'MicroMax 007 (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.717
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63251
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.33c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.253
_exptl_crystal_description       needle
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.406
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.070
_refine_ls_abs_structure_details
;
 Flack x determined using 2304 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.10(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     392
_refine_ls_number_reflns         5999
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0656
_refine_ls_R_factor_gt           0.0613
_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^)+(0.1165P)^2^+0.4546P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1706
_refine_ls_wR_factor_ref         0.1740
_reflns_Friedel_coverage         0.903
_reflns_Friedel_fraction_full    0.987
_reflns_Friedel_fraction_max     0.935
_reflns_number_gt                5422
_reflns_number_total             5999
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob00586d2.cif
_cod_data_source_block           chenweihao_l-p18_collect
_cod_depositor_comments
;
Adding full bibliography for 7159942--7159943.cif.

2024-10-18
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C34 H44 O8'
_cod_original_formula_weight         580.69
_cod_original_formula_moiety         '2(C17 H22 O4)'
_cod_original_formula_units_Z            2
_cod_database_code               7159943
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C70 H90 O14 '
_shelx_estimated_absorpt_t_max   0.972
_shelx_estimated_absorpt_t_min   0.870
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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:
 C14'(H14'), C7(H7), C7'(H7'), C14(H14)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10C,H10D), C10'(H10A,H10B), C15'(H15A,H15B), C15(H15C,H15D)
2.c Aromatic/amide H refined with riding coordinates:
 C4'(H4'), C3'(H3'A), C4(H4), C3(H3), C1'(H1'), C1(H1)
2.d Idealised Me refined as rotating group:
 C12(H12D,H12E,H12F), C11(H11D,H11E,H11F), C12'(H12A,H12B,H12C), C16'(H16A,
 H16B,H16C), C11'(H11A,H11B,H11C), C17'(H17A,H17B,H17C), C17(H17D,H17E,H17F),
 C16(H16D,H16E,H16F)
2.e Idealised tetrahedral OH refined as rotating group:
 O3'(H3')
;
_shelx_res_checksum              17720
_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 1.845
_oxdiff_exptl_absorpt_empirical_full_min 0.464