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_4518585
_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         'C14 H21.99 O5'
_chemical_formula_sum            'C13.99 H21.99 O5'
_chemical_formula_weight         270.24
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2018-10-24
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 105.643(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.3118(2)
_cell_length_b                   6.42450(10)
_cell_length_c                   11.7079(2)
_cell_measurement_reflns_used    4512
_cell_measurement_temperature    104(6)
_cell_measurement_theta_max      73.8560
_cell_measurement_theta_min      7.8420
_cell_volume                     746.90(2)
_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 (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      104(6)
_diffrn_detector                 'Pilatus3R 200K-A'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.981
_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    -33.00  10.00   0.50    0.50    --    0.00 -82.00-180.00   86
  2  \w    -22.00   5.00   0.50    0.50    --    0.00 -82.00  60.00   54
  3  \w    -51.00 -24.00   0.50    0.50    --    0.00 -19.00  60.00   54
  4  \w    -29.00  28.00   0.50    0.50    --    0.00 -82.00 -30.00  114
  5  \w    -26.00   2.00   0.50    0.50    --    0.00 -82.00-150.00   56
  6  \w    -80.00 -55.00   0.50    0.50    --    0.00 -19.00  60.00   50
  7  \w    -19.00  12.00   0.50    0.50    --    0.00 -19.00  60.00   62
  8  \w     12.00  85.00   0.50    0.80    --   95.20 -61.00-150.00  146
  9  \w     78.00 185.00   0.50    0.80    --   95.20  45.00  60.00  214
 10  \w    153.00 181.00   0.50    0.80    --   95.20  77.00 -90.00   56
 11  \w    146.00 175.00   0.50    0.80    --   95.20  82.00-120.00   58
 12  \w     90.00 140.00   0.50    0.80    --   95.20  82.00-120.00  100
 13  \w     12.00  72.00   0.50    0.80    --   95.20 -82.00-150.00  120
 14  \w     78.00 127.00   0.50    0.80    --   95.20 -82.00-150.00   98
 15  \w     79.00 149.00   0.50    0.80    --   95.20  30.00-120.00  140
 16  \w     12.00 116.00   0.50    0.80    --   95.20 -15.00  30.00  208
 17  \w     79.00 161.00   0.50    0.80    --   95.20  30.00   0.00  164
 18  \w     76.00 180.00   0.50    0.80    --   95.20  45.00  90.00  208
 19  \w     94.00 120.00   0.50    0.80    --   95.20  82.00-150.00   52
 20  \w    137.00 160.50   0.50    0.80    --   95.20  82.00-150.00   47
;
_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      0.0305006000
_diffrn_orient_matrix_UB_12      0.0404706000
_diffrn_orient_matrix_UB_13      -0.1199143000
_diffrn_orient_matrix_UB_21      -0.1016563000
_diffrn_orient_matrix_UB_22      0.1810246000
_diffrn_orient_matrix_UB_23      -0.0243747000
_diffrn_orient_matrix_UB_31      0.1130507000
_diffrn_orient_matrix_UB_32      0.1519334000
_diffrn_orient_matrix_UB_33      0.0609938000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_av_unetI/netI     0.0387
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5985
_diffrn_reflns_point_group_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.936
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.031
_diffrn_reflns_theta_min         3.921
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'MicroMax 007 (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.748
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56717
_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    1.202
_exptl_crystal_description       needle
_exptl_crystal_F_000             292
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.133
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
;
 Flack x determined using 1124 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         2842
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.086
_refine_ls_R_factor_all          0.0357
_refine_ls_R_factor_gt           0.0339
_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^)+(0.0582P)^2^+0.0305P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0921
_refine_ls_wR_factor_ref         0.0927
_reflns_Friedel_coverage         0.747
_reflns_Friedel_fraction_full    0.949
_reflns_Friedel_fraction_max     0.882
_reflns_number_gt                2723
_reflns_number_total             2842
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ao0c06218_si_003.cif
_cod_data_source_block           guocui_4-10-4_collect
_cod_database_code               4518585
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C28 H42 O10 '
_shelx_estimated_absorpt_t_max   0.964
_shelx_estimated_absorpt_t_min   0.807
_reflns_odcompleteness_completeness 99.93
_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. Others
 Sof(H10C)=Sof(H10D)=Sof(C11A)=Sof(H11D)=Sof(H11E)=Sof(H11F)=1-FVAR(1)
 Sof(H10A)=Sof(H10B)=Sof(C11)=Sof(H11A)=Sof(H11B)=Sof(H11C)=FVAR(1)
 Sof(H9B)=Sof(C12A)=Sof(H12D)=Sof(H12E)=Sof(H12F)=FVAR(2)
 Sof(H9A)=Sof(C12)=Sof(H12A)=Sof(H12B)=Sof(H12C)=FVAR(3)
3.a Ternary CH refined with riding coordinates:
 C6(H6), C9(H9A), C9(H9B)
3.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C10(H10C,H10D)
3.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C13(H13A,H13B,H13C), C12(H12A,H12B,
 H12C), C11(H11A,H11B,H11C), C11A(H11D,H11E,H11F), C12A(H12D,H12E,H12F)
3.d Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_shelx_res_checksum              46771
_shelx_hkl_checksum              55215
_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 2.063
_oxdiff_exptl_absorpt_empirical_full_min 0.486