Asperones A–E, five dimeric polyketides with new carbon skeletons from the fungus Aspergillus sp. AWG 1–15
Yin, Guo-Ping; Wu, Ya-Rong; Han, Chao; Wang, Xiao-Bing; Gao, Hong-Liang; Yin, Yong; Kong, Ling-Yi; Yang, Ming-Hua; Organic Chemistry Frontiers 5 (2018) 2432–; doi:10.1039/C8QO00070K

data_1554255
_publ_section_title
;
 Asperones A--E, five dimeric polyketides with new carbon skeletons from
 the fungus Aspergillus sp. AWG 1--15
;
_journal_issue                   16
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              2432
_journal_paper_doi               10.1039/C8QO00070K
_journal_volume                  5
_journal_year                    2018
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C28 H36 O8, H2 O'
_chemical_formula_sum            'C28 H38 O9'
_chemical_formula_weight         518.58
_chemical_name_systematic        15-13
_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'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2017-06-09
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2017.05.22 svn.r3414 for OlexSys, GUI svn.r5347)
;
_audit_update_record
;
2017-09-08 deposited with the CCDC.
2018-03-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.3949(9)
_cell_length_b                   15.0525(16)
_cell_length_c                   22.267(2)
_cell_measurement_reflns_used    9961
_cell_measurement_temperature    173
_cell_measurement_theta_max      70.963
_cell_measurement_theta_min      3.54
_cell_volume                     2813.8(5)
_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      173
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.972
_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  0.0425
_diffrn_reflns_av_unetI/netI     0.0227
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            33212
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         71.032
_diffrn_reflns_theta_min         3.544
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.750
_exptl_absorpt_correction_T_max  0.7534
_exptl_absorpt_correction_T_min  0.6758
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0899 before and 0.0582 after correction. The Ratio of minimum to maximum transmission is 0.8970. The \l/2 correction factor is 0.00150.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.224
_exptl_crystal_description       block
_exptl_crystal_F_000             1112
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.156
_refine_diff_density_min         -0.162
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details
;
 Flack x determined using 2129 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     346
_refine_ls_number_reflns         5259
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0338
_refine_ls_R_factor_gt           0.0326
_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^)+(0.0520P)^2^+0.3603P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0864
_refine_ls_wR_factor_ref         0.0873
_reflns_Friedel_coverage         0.750
_reflns_Friedel_fraction_full    0.993
_reflns_Friedel_fraction_max     0.959
_reflns_number_gt                5086
_reflns_number_total             5259
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8qo00070k2.cif
_cod_data_source_block           cu_2017458_0m_a
_cod_original_cell_volume        2813.7(5)
_cod_database_code               1554255
_shelx_shelxl_version_number     2014/7
_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, All O(H,H) groups
2.a Free rotating group:
 O9(H9A,H9B)
2.b Ternary CH refined with riding coordinates:
 C9(H9), C10(H10), C8(H8), C2(H2), C3(H3)
2.c Secondary CH2 refined with riding coordinates:
 C23(H23A,H23B)
2.d Aromatic/amide H refined with riding coordinates:
 C19(H19), C20(H20), C21(H21), C22(H22)
2.e Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C28(H28A,H28B,H28C), C26(H26A,H26B,H26C), C4(H4A,H4B,
 H4C), C25(H25A,H25B,H25C), C1(H1A,H1B,H1C), C27(H27A,H27B,H27C), C24(H24A,H24B,
 H24C)
2.f Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_olex2_submission_special_instructions 'No special instructions were received'