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_7159942
_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         'C18 H20 O5'
_chemical_formula_sum            'C18 H20 O5'
_chemical_formula_weight         316.34
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc2d9ysg
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.4408(6)
_cell_length_b                   10.6295(14)
_cell_length_c                   26.948(3)
_cell_measurement_reflns_used    2116
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      73.2900
_cell_measurement_theta_min      5.3010
_cell_volume                     1558.5(3)
_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      99.99(10)
_diffrn_detector                 'Pilatus3R 200K-A'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.983
_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    -80.00 -43.00   0.50    3.00    --    0.00 -19.00 -60.00   74
  2  \w    -10.00  30.00   0.50    3.00    --    0.00 -82.00-150.00   80
  3  \w    -40.00  14.00   0.50    3.00    --    0.00 -19.00 -60.00  108
  4  \w     11.00 109.00   0.50   20.50    --   95.80 -30.00-120.00  196
  5  \w     10.00  73.00   0.50   20.50    --   95.80 -77.00   0.00  126
  6  \w     96.00 131.00   0.50   20.50    --   95.80  82.00 -90.00   70
  7  \w      6.00  92.00   0.50   20.50    --   95.80 -61.00 150.00  172
  8  \w      8.00 110.00   0.50   20.50    --   95.80 -45.00-150.00  204
  9  \w      8.00 124.00   0.50   20.50    --   95.80 -82.00 150.00  232
;
_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      -0.1655413000
_diffrn_orient_matrix_UB_12      0.0849037000
_diffrn_orient_matrix_UB_13      -0.0320820000
_diffrn_orient_matrix_UB_21      -0.2206754000
_diffrn_orient_matrix_UB_22      -0.0314661000
_diffrn_orient_matrix_UB_23      0.0335309000
_diffrn_orient_matrix_UB_31      0.0631090000
_diffrn_orient_matrix_UB_32      0.1132130000
_diffrn_orient_matrix_UB_33      0.0334137000
_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  0.0673
_diffrn_reflns_av_unetI/netI     0.0862
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            7480
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.246
_diffrn_reflns_theta_min         3.280
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'MicroMax 007 (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.809
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73579
_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    1.348
_exptl_crystal_description       plate
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.589
_refine_diff_density_min         -0.331
_refine_diff_density_rms         0.095
_refine_ls_abs_structure_details
;
 Flack x determined using 699 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.3(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         3064
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.107
_refine_ls_R_factor_all          0.1047
_refine_ls_R_factor_gt           0.0784
_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^)+(0.1195P)^2^+2.3705P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2248
_refine_ls_wR_factor_ref         0.2448
_reflns_Friedel_coverage         0.663
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.939
_reflns_number_gt                2264
_reflns_number_total             3064
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob00586d2.cif
_cod_data_source_block           p16_collect
_cod_depositor_comments
'Adding full bibliography for 7159942--7159943.cif.'
_cod_database_code               7159942
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C72 H80 O20 '
_shelx_estimated_absorpt_t_max   0.976
_shelx_estimated_absorpt_t_min   0.931
_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, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C15(H15), C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3), C4(H4)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C13(H13A,H13B,H13C), C18(H18A,H18B,H18C), C17(H17A,H17B,
 H17C)
;
_shelx_res_checksum              1329
_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 1.688
_oxdiff_exptl_absorpt_empirical_full_min 0.719