Discovery of a Dimeric Zinc Complex and Five Cyclopentenone Derivatives from the Sponge-Associated Fungus Aspergillus ochraceopetaliformis
Guo, Cui; Wang, Pei; Pang, Xiaoyan; Lin, Xiuping; Liao, Shengrong; Yang, Bin; Zhou, Xuefeng; Wang, Junfeng; Liu, Yonghong; ACS Omega  (2021) –; doi:10.1021/acsomega.0c06218

data_4518586
_publ_section_title
;
 Discovery of a Dimeric Zinc Complex and Five Cyclopentenone Derivatives
 from the Sponge-Associated Fungus Aspergillus ochraceopetaliformis
;
_journal_name_full               'ACS Omega'
_journal_paper_doi               10.1021/acsomega.0c06218
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety
'0.67(C48 H74.42 N8 O12 Zn2), 0.33(C48 H76 N8 O12 Zn2)'
_chemical_formula_sum            'C48 H76.36 N8 O12 Zn2'
_chemical_formula_weight         1088.27
_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   geom
_audit_creation_date             2018-10-22
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 89.6390(10)
_cell_angle_gamma                90
_cell_formula_units_Z            6
_cell_length_a                   11.85990(10)
_cell_length_b                   24.2844(3)
_cell_length_c                   29.9249(3)
_cell_measurement_reflns_used    31334
_cell_measurement_temperature    99.9(3)
_cell_measurement_theta_max      73.6840
_cell_measurement_theta_min      4.0080
_cell_volume                     8618.52(16)
_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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.9(3)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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     -3.00  31.00   0.50    5.00    --    0.00 -82.00-180.00   68
  2  \w    -24.00  29.00   0.50    5.00    --    0.00 -82.00 -90.00  106
  3  \w    -43.00   2.00   0.50    5.00    --    0.00 -77.00  60.00   90
  4  \w    -22.00  13.00   0.50    5.00    --    0.00 -82.00 120.00   70
  5  \w    -32.00  -5.00   0.50    5.00    --    0.00 -82.00-180.00   54
  6  \w      6.00  39.00   0.50   30.00    --   94.60 -82.00 -30.00   66
  7  \w      7.00 107.00   0.50   30.00    --   94.60 -30.00 120.00  200
  8  \w     74.00 156.00   0.50   30.00    --   94.60  61.00 150.00  164
  9  \w     23.00  49.00   0.50   30.00    --   94.60 -82.00  30.00   52
 10  \w      5.00 112.00   0.50   30.00    --   94.60 -61.00  30.00  214
 11  \w     79.00 117.00   0.50   30.00    --   94.60 -82.00  30.00   76
 12  \w     57.00 122.00   0.50   30.00    --   94.60 -82.00 -30.00  130
 13  \w     60.00 116.00   0.50   30.00    --   94.60 -15.00 150.00  112
 14  \w      9.00 106.00   0.50   30.00    --   94.60 -61.00 -30.00  194
 15  \w     19.00  48.00   0.50   30.00    --   94.60 -15.00 150.00   58
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1031401000
_diffrn_orient_matrix_UB_12      0.0354023000
_diffrn_orient_matrix_UB_13      -0.0126768000
_diffrn_orient_matrix_UB_21      -0.0624579000
_diffrn_orient_matrix_UB_22      0.0519516000
_diffrn_orient_matrix_UB_23      0.0162884000
_diffrn_orient_matrix_UB_31      0.0483434000
_diffrn_orient_matrix_UB_32      -0.0084169000
_diffrn_orient_matrix_UB_33      0.0471689000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0374
_diffrn_reflns_av_unetI/netI     0.0482
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            50553
_diffrn_reflns_point_group_measured_fraction_full 0.835
_diffrn_reflns_point_group_measured_fraction_max 0.835
_diffrn_reflns_theta_full        67.080
_diffrn_reflns_theta_max         67.080
_diffrn_reflns_theta_min         3.929
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.530
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71718
_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 yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.258
_exptl_crystal_description       block
_exptl_crystal_F_000             3458
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.397
_refine_diff_density_min         -0.487
_refine_diff_density_rms         0.096
_refine_ls_abs_structure_details
;
 Flack x determined using 7724 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.050(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     2063
_refine_ls_number_reflns         25698
_refine_ls_number_restraints     41
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0830
_refine_ls_R_factor_gt           0.0777
_refine_ls_shift/su_max          1.290
_refine_ls_shift/su_mean         0.019
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1298P)^2^+12.5877P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2125
_refine_ls_wR_factor_ref         0.2168
_reflns_Friedel_coverage         0.632
_reflns_Friedel_fraction_full    0.664
_reflns_Friedel_fraction_max     0.664
_reflns_number_gt                22998
_reflns_number_total             25698
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ao0c06218_si_002.cif
_cod_data_source_block           guocui_4_4_1_collect_sq
_cod_database_code               4518586
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.862
_shelx_estimated_absorpt_t_min   0.803
_reflns_odcompleteness_completeness 99.67
_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
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 C1AB-C21A
 1.54 with sigma of 0.02
 C1AB-C11
 1.54 with sigma of 0.02
 C1AB-C5BB
 1.54 with sigma of 0.02
 C24-C113
 1.54 with sigma of 0.02
 C113-C10
 1.54 with sigma of 0.02
 C14-C10A
 1.54 with sigma of 0.02
 C14-C24A
 1.54 with sigma of 0.02
 C3CB-C6CB
 1.54 with sigma of 0.01
 C6CB-C5CB
 1.54 with sigma of 0.01
 C6CB-C6BB
 1.54 with sigma of 0.01
 C2CB-C0CB
 2.5 with sigma of 0.04
 C21A-C5BB
 2.5 with sigma of 0.04
 C10A-C24A
 2.5 with sigma of 0.04
 C2CB-C53
 2.5 with sigma of 0.04
 C2BA-C2AA \\sim C2BA-C2AB
 with sigma of 0.02
 C2AA-C3BA \\sim C2AB-C3BB
 with sigma of 0.02
 C2AA-C7AA \\sim C2AB-C7AB
 with sigma of 0.02
 C2BA-C3BA \\sim C2BA-C3BB
 with sigma of 0.04
 C2BA-C7AA \\sim C2BA-C7AB
 with sigma of 0.04
 C3BA-C7AA \\sim C3BB-C7AB
 with sigma of 0.04
 C7BA-C2CA \\sim C7BA-C2CB
 with sigma of 0.02
 C7BA-C0CA \\sim C7BA-C0CB
 with sigma of 0.02
 C95-C97 \\sim C95-C97A
 with sigma of 0.02
 C97-C9BA \\sim C97A-C9BB
 with sigma of 0.02
 C97-C1CA \\sim C97A-C1CB
 with sigma of 0.02
 C95-C9BA \\sim C95-C9BB
 with sigma of 0.04
 C95-C1CA \\sim C95-C1CB
 with sigma of 0.04
 C9BA-C1CA \\sim C9BB-C1CB
 with sigma of 0.04
 C169-C170 \\sim C169-C17
 with sigma of 0.02
 C170-C5AA \\sim C17-C5AB
 with sigma of 0.02
 C170-C8BA \\sim C17-C8BB
 with sigma of 0.02
 C169-C5AA \\sim C169-C5AB
 with sigma of 0.04
 C169-C8BA \\sim C169-C8BB
 with sigma of 0.04
 C5AA-C8BA \\sim C5AB-C8BB
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
Uanis(C24) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C3BB) = Uanis(C3BA)
Uanis(C7AB) = Uanis(C7AA)
Uanis(C2AB) = Uanis(C2AA)
Uanis(C2CB) = Uanis(C2CA)
Uanis(C0CB) = Uanis(C0CA)
Uanis(C106) = Uanis(C6)
Uanis(C0AA) = Uanis(C0AB)
Uanis(N105) = Uanis(N1)
Uanis(C3CA) = Uanis(C3CB)
Uanis(O1) = Uanis(O1A)
Uanis(C36) = Uanis(C36A)
Uanis(C37) = Uanis(C37A)
Uanis(C4BA) = Uanis(C4BB)
Uanis(C1CA) = Uanis(C1CB)
Uanis(C9BB) = Uanis(C9BA)
Uanis(C154) = Uanis(C11)
Uanis(C1AA) = Uanis(C1AB)
Uanis(C21) = Uanis(C21A)
Uanis(C5BA) = Uanis(C5BB)
Uanis(C97A) = Uanis(C97)
Uanis(C1CB) = Uanis(C1CA)
Uanis(C113) = Uanis(C14)
Uanis(C24) = Uanis(C24A)
Uanis(C10) = Uanis(C10A)
Uanis(C5CA) = Uanis(C5CB)
Uanis(C8BB) = Uanis(C8BA)
Uanis(C5AB) = Uanis(C5AA)
Uanis(C17) = Uanis(C170)
Uanis(C4CA) = Uanis(C6CB)
Uanis(C6BA) = Uanis(C6BB)
4. Others
 Sof(H2BA)=Sof(C2AB)=Sof(H2AB)=Sof(C7AB)=Sof(H7AD)=Sof(H7AE)=Sof(H7AF)=
 Sof(C3BB)=Sof(H3BD)=Sof(H3BE)=Sof(H3BF)=1-FVAR(1)
 Sof(C2AA)=Sof(H2AA)=Sof(C3BA)=Sof(H3BA)=Sof(H3BB)=Sof(H3BC)=Sof(C7AA)=
 Sof(H7AA)=Sof(H7AB)=Sof(H7AC)=FVAR(1)
 Sof(H7BB)=Sof(C0CB)=Sof(H0CD)=Sof(H0CE)=Sof(H0CF)=Sof(C2CB)=Sof(H2CD)=
 Sof(H2CE)=Sof(H2CF)=1-FVAR(2)
 Sof(H7BA)=Sof(C2CA)=Sof(H2CA)=Sof(H2CB)=Sof(H2CC)=Sof(C0CA)=Sof(H0CA)=
 Sof(H0CB)=Sof(H0CC)=FVAR(2)
 Sof(C6)=Sof(C0AB)=Sof(H0AB)=Sof(N1)=1-FVAR(3)
 Sof(N105)=Sof(C106)=Sof(C0AA)=Sof(H0AA)=FVAR(3)
 Sof(C3CB)=Sof(H3CB)=Sof(O1A)=Sof(H1A)=Sof(C5CB)=Sof(H5CD)=Sof(H5CE)=Sof(H5CF)=
 Sof(C6CB)=Sof(H6CB)=Sof(C6BB)=Sof(H6BD)=Sof(H6BE)=Sof(H6BF)=1-FVAR(4)
 Sof(O1)=Sof(H1)=Sof(C3CA)=Sof(H3CA)=Sof(C4CA)=Sof(H4CA)=Sof(C5CA)=Sof(H5CA)=
 Sof(H5CB)=Sof(H5CC)=Sof(C6BA)=Sof(H6BA)=Sof(H6BB)=Sof(H6BC)=FVAR(4)
 Sof(H35C)=Sof(H35D)=Sof(C36A)=Sof(H36A)=Sof(C37A)=Sof(H37D)=Sof(H37E)=
 Sof(H37F)=Sof(C4BB)=Sof(H4BD)=Sof(H4BE)=Sof(H4BF)=1-FVAR(5)
 Sof(H35A)=Sof(H35B)=Sof(C36)=Sof(H36)=Sof(C37)=Sof(H37A)=Sof(H37B)=Sof(H37C)=
 Sof(C4BA)=Sof(H4BA)=Sof(H4BB)=Sof(H4BC)=FVAR(5)
 Sof(H95A)=Sof(C97A)=Sof(H97A)=Sof(C9BB)=Sof(H9BD)=Sof(H9BE)=Sof(H9BF)=
 Sof(C1CB)=Sof(H1CD)=Sof(H1CE)=Sof(H1CF)=1-FVAR(6)
 Sof(H95)=Sof(C97)=Sof(H97)=Sof(C9BA)=Sof(H9BA)=Sof(H9BB)=Sof(H9BC)=Sof(C1CA)=
 Sof(H1CA)=Sof(H1CB)=Sof(H1CC)=FVAR(6)
 Sof(C11)=Sof(H11)=Sof(C1AB)=Sof(C21A)=Sof(H21D)=Sof(C5BB)=Sof(H5BD)=Sof(H5BE)=
 Sof(H5BF)=1-FVAR(7)
 Sof(C154)=Sof(H15M)=Sof(H15N)=Sof(C1AA)=Sof(H1AA)=Sof(C21)=Sof(H21A)=
 Sof(H21B)=Sof(H21C)=Sof(C5BA)=Sof(H5BA)=Sof(H5BB)=Sof(H5BC)=FVAR(7)
 Sof(H11C)=Sof(H11D)=Sof(C14)=Sof(H14)=Sof(C24A)=Sof(H24D)=Sof(H24E)=Sof(H24F)=
 Sof(C10A)=Sof(H10O)=Sof(H10P)=Sof(H10Q)=1-FVAR(8)
 Sof(H11A)=Sof(H11B)=Sof(C113)=Sof(H113)=Sof(C10)=Sof(H10L)=Sof(H10M)=
 Sof(H10N)=Sof(C24)=Sof(H24A)=Sof(H24B)=Sof(H24C)=FVAR(8)
 Sof(H16E)=Sof(H16F)=Sof(C17)=Sof(H17)=Sof(C8BB)=Sof(H8BD)=Sof(H8BE)=Sof(H8BF)=
 Sof(C5AB)=Sof(H5AD)=Sof(H5AE)=Sof(H5AF)=1-FVAR(9)
 Sof(H16C)=Sof(H16D)=Sof(C170)=Sof(H170)=Sof(C5AA)=Sof(H5AA)=Sof(H5AB)=
 Sof(H5AC)=Sof(C8BA)=Sof(H8BA)=Sof(H8BB)=Sof(H8BC)=FVAR(9)
5.a Ternary CH refined with riding coordinates:
 C48(H48), C165(H165), C107(H107), C150(H150), C155(H155), C171(H171),
 C149(H149), C161(H161), C95(H95), C95(H95A), C76(H76), C164(H164), C108(H108),
 C41(H41), C49(H49), C99(H99), C180(H180), C156(H156), C172(H172), C46(H46),
 C71(H71), C38(H38), C177(H177), C97(H97), C36(H36), C77(H77), C113(H113),
 C170(H170), C42(H42), C104(H104), C39(H39), C3(H3), C2AA(H2AA), C2AB(H2AB),
 C7BA(H7BA), C7BA(H7BB), C3CA(H3CA), C4CA(H4CA), C3CB(H3CB), C6CB(H6CB),
 C36A(H36A), C97A(H97A), C1AA(H1AA), C11(H11), C14(H14), C17(H17)
5.b Secondary CH2 refined with riding coordinates:
 C35(H35A,H35B), C35(H35C,H35D), C98(H98A,H98B), C176(H17D,H17E), C45(H45A,
 H45B), C160(H16A,H16B), C53(H53A,H53B), C169(H16C,H16D), C169(H16E,H16F),
 C70(H70A,H70B), C112(H11A,H11B), C112(H11C,H11D), C103(H10G,H10H), C154(H15M,
 H15N)
5.c Aromatic/amide H refined with riding coordinates:
 C65(H65), C133(H133), C5(H5), C29(H29), C143(H143), C90(H90), C119(H119),
 C19(H19), C80(H80), C127(H127), C13(H13), C0AA(H0AA), C2BA(H2BA), C0AB(H0AB),
 C21A(H21D)
5.d Idealised Me refined as rotating group:
 C157(H15A,H15B,H15C), C173(H17F,H17G,H17H), C101(H10A,H10B,H10C), C109(H10D,
 H10E,H10F), C110(H11E,H11F,H11G), C151(H15D,H15E,H15F), C158(H15G,H15H,H15I),
 C72(H72A,H72B,H72C), C166(H16G,H16H,H16I), C152(H15J,H15K,H15L), C179(H17A,
 H17B,H17C), C50(H50A,H50B,H50C), C174(H17I,H17J,H17K), C81(H81A,H81B,H81C),
 C163(H16J,H16K,H16L), C43(H43A,H43B,H43C), C100(H10I,H10J,H10K), C167(H16M,
 H16N,H16O), C78(H78A,H78B,H78C), C37(H37A,H37B,H37C), C51(H51A,H51B,H51C),
 C162(H16P,H16Q,H16R), C178(H17L,H17M,H17N), C1(H1B,H1C,H1D), C2(H2A,H2B,H2C),
 C3AA(H3AA,H3AB,H3AC), C6AA(H6AA,H6AB,H6AC), C8AA(H8AA,H8AB,H8AC), C9(H9A,H9B,
 H9C), C10(H10L,H10M,H10N), C9AA(H9AA,H9AB,H9AC), C5AA(H5AA,H5AB,H5AC),
 C4AA(H4AA,H4AB,H4AC), C8BA(H8BA,H8BB,H8BC), C1BA(H1BA,H1BB,H1BC), C4BA(H4BA,
 H4BB,H4BC), C0BA(H0BA,H0BB,H0BC), C9BA(H9BA,H9BB,H9BC), C1CA(H1CA,H1CB,H1CC),
 C3BA(H3BA,H3BB,H3BC), C7AA(H7AA,H7AB,H7AC), C7AB(H7AD,H7AE,H7AF), C3BB(H3BD,
 H3BE,H3BF), C2CA(H2CA,H2CB,H2CC), C0CA(H0CA,H0CB,H0CC), C0CB(H0CD,H0CE,H0CF),
 C2CB(H2CD,H2CE,H2CF), C5CA(H5CA,H5CB,H5CC), C5CB(H5CD,H5CE,H5CF), C37A(H37D,
 H37E,H37F), C4BB(H4BD,H4BE,H4BF), C24(H24A,H24B,H24C), C9BB(H9BD,H9BE,H9BF),
 C1CB(H1CD,H1CE,H1CF), C21(H21A,H21B,H21C), C5BA(H5BA,H5BB,H5BC), C5BB(H5BD,
 H5BE,H5BF), C24A(H24D,H24E,H24F), C10A(H10O,H10P,H10Q), C8BB(H8BD,H8BE,H8BF),
 C5AB(H5AD,H5AE,H5AF), C6BA(H6BA,H6BB,H6BC), C6BB(H6BD,H6BE,H6BF)
5.e Idealised tetrahedral OH refined as rotating group:
 O159(H159), O52(H52), O175(H175), O111(H111), O44(H44), O168(H168),
 O153(H153), O96(H96), O40(H40), O79(H79), O182(H182), O1(H1), O1A(H1A)
;
_shelx_res_checksum              94472
_shelx_hkl_checksum              60866
_shelx_fab_checksum              26204
_platon_squeeze_void_probe_radius 1.20
_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 1.929
_oxdiff_exptl_absorpt_empirical_full_min 0.548