Absolute Configuration and Biological Activities of Meroterpenoids from an Endophytic Fungus of <i>Lycium barbarum</i>.
Long, Yi; Tang, Ting; Wang, Li-Ying; He, Bin; Gao, Kun; Journal of natural products 82 (2019) 2229–2237; doi:10.1021/acs.jnatprod.9b00288

data_1552608
_publ_section_title
;
 Absolute Configuration and Biological Activities of Meroterpenoids from
 an Endophytic Fungus of <i>Lycium barbarum</i>.
;
_journal_issue                   8
_journal_name_full               'Journal of natural products'
_journal_page_first              2229
_journal_page_last               2237
_journal_paper_doi               10.1021/acs.jnatprod.9b00288
_journal_volume                  82
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         '2(C30 H45 N O8)'
_chemical_formula_sum            'C60 H90 N2 O16'
_chemical_formula_weight         1095.33
_space_group_crystal_system      hexagonal
_space_group_IT_number           169
_space_group_name_Hall           'P 61'
_space_group_name_H-M_alt        'P 61'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2019-03-12
_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                   36.4492(5)
_cell_length_b                   36.4492(5)
_cell_length_c                   9.48811(18)
_cell_measurement_reflns_used    19840
_cell_measurement_temperature    292.2(5)
_cell_measurement_theta_max      69.4430
_cell_measurement_theta_min      5.4040
_cell_volume                     10916.6(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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      292.2(5)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -58.00  -26.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  137.0000 -145.0000 32

  2 omega  -76.00  -31.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  -57.0000  -30.0000 45

  3 omega  -49.00   13.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  -57.0000 -120.0000 62

  4 omega  -82.00  -34.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  178.0000  -60.0000 48

  5 omega   65.00  130.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  174.0000  147.0000 65

  6 omega   32.00   78.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000 -120.0000 46

  7 omega   55.00  121.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000  150.0000 66

  8 omega   32.00   64.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000  -30.0000 32

  9 omega   87.00  115.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000  -30.0000 28

 10 omega   22.00   48.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   78.0000  -71.8663 26

 11 omega   36.00  115.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000    0.0000 79

 12 omega   76.00  112.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -150.0000 36

 13 omega   69.00   95.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   25.0000  -30.0000 26

 14 omega   76.00  101.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -60.0000 25

 15 omega   56.00   89.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000    0.0000 33

 16 omega   77.00  103.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   75.0000  -45.4713 26

 17 omega   85.00  159.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   50.0000  -57.2294 74

 18 omega   81.00  107.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   38.0000  -90.0000 26

 19 omega   84.00  110.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   63.0000  -60.0000 26

 20 omega   71.00   97.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000  150.0000 26

 21 omega   82.00  116.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   38.0000 -120.0000 34

 22 omega   82.00  108.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   67.0000 -120.5442 26

 23 omega   81.00  107.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   38.0000  -30.0000 26

 24 omega   90.00  115.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -123.0000  -56.0000 25

 25 omega  105.00  174.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   63.0000   90.0000 69

 26 omega  121.00  161.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -150.0000 40

 27 omega  134.00  172.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   63.0000   60.0000 38

 28 omega   84.00  110.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   63.0000 -120.0000 26

 29 omega   84.00  175.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   63.0000  -90.0000 91

 30 omega  148.00  174.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   63.0000   30.0000 26

 31 omega   76.00  177.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -120.0000 101

 32 omega   77.00  103.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   25.0000  -90.0000 26

 33 omega   76.00  102.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -90.0000 26

 34 omega   86.00  111.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   50.0000  -90.0000 25

 35 omega   86.00  112.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   50.0000 -120.0000 26

 36 omega  128.00  153.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -60.0000 25

 37 omega   71.00   97.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   19.0000  -59.0659 26

 38 omega   38.00   63.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000  150.0000 25

 39 omega   81.00  106.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   69.0000  -99.5734 25

 40 omega   77.00  103.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   25.0000  -60.0000 26

 41 omega   75.00  100.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   25.0000    0.0000 25

 42 omega  103.00  129.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -91.0000   90.0000 26

 43 omega   83.00  108.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   64.0000 -100.0224 25
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0487590000
_diffrn_orient_matrix_UB_12      0.0256876000
_diffrn_orient_matrix_UB_13      -0.0040609000
_diffrn_orient_matrix_UB_21      0.0017695000
_diffrn_orient_matrix_UB_22      -0.0400887000
_diffrn_orient_matrix_UB_23      0.0394367000
_diffrn_orient_matrix_UB_31      -0.0008238000
_diffrn_orient_matrix_UB_32      -0.0106943000
_diffrn_orient_matrix_UB_33      -0.1574853000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0628
_diffrn_reflns_av_unetI/netI     0.0587
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       42
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_k_max       43
_diffrn_reflns_limit_k_min       -43
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            74154
_diffrn_reflns_point_group_measured_fraction_full 0.953
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_theta_full        66.565
_diffrn_reflns_theta_max         66.565
_diffrn_reflns_theta_min         3.705
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.586
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.40751
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light violet'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    violet
_exptl_crystal_density_diffrn    1.000
_exptl_crystal_description       block
_exptl_crystal_F_000             3552
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.362
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details
;
 Flack x determined using 3862 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.10(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     733
_refine_ls_number_reflns         12246
_refine_ls_number_restraints     26
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0737
_refine_ls_R_factor_gt           0.0609
_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^)+(0.1079P)^2^+0.9736P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1552
_refine_ls_wR_factor_ref         0.1681
_reflns_Friedel_coverage         0.791
_reflns_Friedel_fraction_full    0.901
_reflns_Friedel_fraction_max     0.901
_reflns_number_gt                10304
_reflns_number_total             12246
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np9b00288_si_002.cif
_cod_data_source_block           longy_1204
_cod_original_cell_volume        10916.6(4)
_cod_database_code               1552608
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.86
_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, All C(H,H,H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 C3AA-C2AA
 1.45 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(C2AA) \\sim Ueq, Uanis(C4AA) \\sim Ueq, Uanis(C3AA) \\sim Ueq: with sigma
of 0.01 and sigma for terminal atoms of 0.02
Uanis(C1AA) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
4. Others
 Fixed Sof: H3AA(0.5) H3AB(0.5) H3AC(0.5) H3AD(0.5) C4AA(0.6) H4AA(0.6)
 H4AB(0.6) H4AC(0.6) C2AA(0.4) H2AA(0.4) H2AB(0.4) H2AC(0.4)
5.a Ternary CH refined with riding coordinates:
 C3(H3), C4(H4A), C5(H5A), C12(H12A), C13(H13A), C17(H17), C21(H21),
 C1BA(H1BA), C4BA(H4BA), C7AA(H7AA), C33(H33), C52(H52), C65(H65), C68(H68)
5.b Secondary CH2 refined with riding coordinates:
 C2(H2C,H2D), C15(H15A,H15B), C16(H16A,H16B), C19(H19A,H19B), C20(H20A,H20B),
 C0AA(H0AA,H0AB), C0BA(H0BA,H0BB), C3AA(H3AA,H3AB), C3AA(H3AC,H3AD), C49(H49A,
 H49B), C53(H53A,H53B)
5.c X=CH2 refined with riding coordinates:
 N1(H1A,H1B), N2(H2A,H2B)
5.d Idealised Me refined as rotating group:
 C1(H1C,H1D,H1E), C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C25(H25A,H25B,
 H25C), C26(H26A,H26B,H26C), C27(H27A,H27B,H27C), C28(H28A,H28B,H28C), C30(H30A,
 H30B,H30C), C1AA(H1AA,H1AB,H1AC), C48(H48A,H48B,H48C), C60(H60A,H60B,H60C),
 C64(H64A,H64B,H64C), C70(H70A,H70B,H70C), C72(H72A,H72B,H72C), C74(H74A,H74B,
 H74C), C4AA(H4AA,H4AB,H4AC), C2AA(H2AA,H2AB,H2AC)
5.e Idealised tetrahedral OH refined as rotating group:
 O4(H4), O5(H5), O12(H12), O13(H13)
;
_shelx_res_checksum              46899
_shelx_hkl_checksum              45613
_olex2_date_sample_data_collection 2018-12-04
_olex2_submission_special_instructions 'No special instructions were received'