Chrodrimanins K-N and Related Meroterpenoids from the Fungus Penicillium sp. SCS-KFD09 Isolated from a Marine Worm, Sipunculus nudus.
Kong, Fan-Dong; Ma, Qing-Yun; Huang, Sheng-Zhuo; Wang, Pei; Wang, Jun-Feng; Zhou, Li-Man; Yuan, Jing-Zhe; Dai, Hao-Fu; Zhao, You-Xing; Journal of natural products 80 (2017) 1039–1047; doi:10.1021/acs.jnatprod.6b01061

data_1545297
_publ_section_title
;
 Chrodrimanins K-N and Related Meroterpenoids from the Fungus Penicillium
 sp. SCS-KFD09 Isolated from a Marine Worm, Sipunculus nudus.
;
_journal_issue                   4
_journal_name_full               'Journal of natural products'
_journal_page_first              1039
_journal_page_last               1047
_journal_paper_doi               10.1021/acs.jnatprod.6b01061
_journal_volume                  80
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C25 H30 O7'
_chemical_formula_sum            'C25 H30 O7'
_chemical_formula_weight         442.49
_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'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2016-11-14
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.9888(4)
_cell_length_b                   12.7811(4)
_cell_length_c                   15.6040(5)
_cell_measurement_reflns_used    9987
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      68.182
_cell_measurement_theta_min      4.023
_cell_volume                     2191.57(13)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      273.15
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0330
_diffrn_reflns_av_unetI/netI     0.0273
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            15924
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.240
_diffrn_reflns_theta_min         4.472
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.802
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6573
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0715 before and 0.0608 after correction.
The Ratio of minimum to maximum transmission is 0.8728.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_description       block
_exptl_crystal_F_000             944
_refine_diff_density_max         0.228
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details
;
 Flack x determined using 1479 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     294
_refine_ls_number_reflns         3976
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0450
_refine_ls_R_factor_gt           0.0415
_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^)+(0.0577P)^2^+0.4863P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1028
_refine_ls_wR_factor_ref         0.1052
_reflns_Friedel_coverage         0.752
_reflns_Friedel_fraction_full    0.986
_reflns_Friedel_fraction_max     0.984
_reflns_number_gt                3714
_reflns_number_total             3976
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np6b01061_si_007.cif
_cod_data_source_block           9_22_12_1_0m
_cod_depositor_comments
'Adding full bibliography for 1545294--1545297.cif.'
_cod_database_code               1545297
_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 Riding coordinates:
 O5(H5), O3(H3), O7(H7)
2.b Ternary CH refined with riding coordinates:
 C9(H9), C7(H7A), C19(H19), C20(H20), C15(H15)
2.c Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C16(H16A,H16B)
2.d Aromatic/amide H refined with riding coordinates:
 C13(H13), C12(H12), C4(H4)
2.e Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C25(H25A,H25B,H25C), C23(H23A,H23B,H23C), C24(H24A,H24B,
 H24C), C22(H22A,H22B,H22C)
;
_shelx_res_checksum              2035
_shelx_hkl_checksum              68515
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'