Bioactive Penicipyrrodiether A, an Adduct of GKK1032 Analogue and Phenol A Derivative, from a Marine-Sourced Fungus Penicillium sp. ZZ380.
Song, Tengfei; Chen, Mengxuan; Ge, Zhi-Wei; Chai, Weiyun; Li, Xing-Cong; Zhang, Zhizhen; Lian, Xiao-Yuan; The Journal of organic chemistry 83 (2018) 13395–13401; doi:10.1021/acs.joc.8b02172

data_4035774
_publ_section_title
;
 Bioactive Penicipyrrodiether A, an Adduct of GKK1032 Analogue and Phenol
 A Derivative, from a Marine-Sourced Fungus Penicillium sp. ZZ380.
;
_journal_issue                   21
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              13395
_journal_page_last               13401
_journal_paper_doi               10.1021/acs.joc.8b02172
_journal_volume                  83
_journal_year                    2018
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C43 H53 N O8'
_chemical_formula_sum            'C43 H53 N O8'
_chemical_formula_weight         711.86
_space_group_crystal_system      hexagonal
_space_group_IT_number           172
_space_group_name_Hall           'P 64'
_space_group_name_H-M_alt        'P 64'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2018-09-25
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            6
_cell_length_a                   28.5703(10)
_cell_length_b                   28.5703(10)
_cell_length_c                   9.3110(4)
_cell_measurement_reflns_used    9698
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      66.9189
_cell_measurement_theta_min      3.0910
_cell_volume                     6582.0(4)
_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    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details
;
  1 omega    9.00  119.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       41.6938   74.0000   13.0000 110

  2 omega  -33.00   37.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       41.6938  -38.0000 -120.0000 70

  3 omega   32.00  177.00   1.0000  120.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   15.0000   90.0000 145

  4 omega   21.00   77.00   1.0000  120.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -45.0000 -120.0000 56

  5 omega   92.00  171.00   1.0000  120.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   74.0000   13.0000 79

  6 omega   95.00  166.00   1.0000  120.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   34.0000  -76.0000 71

  7 omega   15.00  113.00   1.0000  120.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -77.0000 -150.0000 98

  8 omega   66.00  168.00   1.0000  120.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   45.0000 -120.0000 102
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0450618000
_diffrn_orient_matrix_UB_12      0.0196136000
_diffrn_orient_matrix_UB_13      0.1139567000
_diffrn_orient_matrix_UB_21      0.0425936000
_diffrn_orient_matrix_UB_22      0.0313220000
_diffrn_orient_matrix_UB_23      -0.1166863000
_diffrn_orient_matrix_UB_31      -0.0057112000
_diffrn_orient_matrix_UB_32      0.0500204000
_diffrn_orient_matrix_UB_33      0.0282863000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0688
_diffrn_reflns_av_unetI/netI     0.0536
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            28080
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.031
_diffrn_reflns_theta_max         67.031
_diffrn_reflns_theta_min         3.094
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.593
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.47890
_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_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.078
_exptl_crystal_description       plate
_exptl_crystal_F_000             2292
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.18
_platon_squeeze_details
;
TITL 180428_380P 64         R = 0.13
CELL   28.5703   28.5703    9.3110     90.00     90.00    120.00
SPGR P64
Q101 0.430 0.377 0.589 !       3.27 eA-3
C102 0.093 0.499 0.533 !       3.17 eA-3
Q103 0.562 0.510 0.659 !       2.08 eA-3
C104 0.534 0.705 0.679 !       1.31 eA-3
C105 1.000 0.501 0.312 !       1.27 eA-3
C106 0.446 0.845 0.046 !       0.79 eA-3
C107 0.665 0.225 0.210 !       0.78 eA-3
C108 0.460 0.672 0.776 !       0.67 eA-3
C109 0.360 0.804 0.031 !       0.57 eA-3
C110 0.341 0.877 0.971 !       0.57 eA-3
;
_refine_diff_density_max         0.325
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.1(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     480
_refine_ls_number_reflns         7680
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.097
_refine_ls_R_factor_all          0.0935
_refine_ls_R_factor_gt           0.0792
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1547P)^2^+0.5918P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2187
_refine_ls_wR_factor_ref         0.2380
_reflns_Friedel_coverage         0.860
_reflns_Friedel_fraction_full    0.976
_reflns_Friedel_fraction_max     0.976
_reflns_number_gt                6092
_reflns_number_total             7680
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b02172_si_002.cif
_cod_data_source_block           180428_380h1_sq
_cod_original_cell_volume        6582.0(5)
_cod_database_code               4035774
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'c h n o'
_shelx_estimated_absorpt_t_max   0.901
_shelx_estimated_absorpt_t_min   0.764
_reflns_odcompleteness_completeness 99.98
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     64.99
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(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:
 C8(H8), C6(H6), C7(H7A), C19(H19), C18(H18), C13(H13), C1(H1A), C9(H9),
 C26(H26), C25(H25), C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C36(H36A,H36B), C2(H2A,H2B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C31(H31), C35(H35), C32(H32), C34(H34), C39(H39), C11(H11)
2.d X=CH2 refined with riding coordinates:
 C40(H40A,H40B)
2.e Idealised Me refined as rotating group:
 C29(H29A,H29B,H29C), C38(H38A,H38B,H38C), C27(H27A,H27B,H27C), C37(H37A,H37B,
 H37C), C42(H42A,H42B,H42C), C28(H28A,H28B,H28C), C41(H41A,H41B,H41C), C43(H43A,
 H43B,H43C)
2.f Idealised tetrahedral OH refined as rotating group:
 O2(H2), O7(H7), O5(H5)
;
_platon_squeeze_void_probe_radius 1.20
_olex2_submission_special_instructions 'No special instructions were received'