Phloroglucinol heterodimers and bis-indolyl alkaloids from the sponge-derived fungus Aspergillus sp. SCSIO 41018
Guo, Cui; Wang, Pei; Lin, Xiuping; Salendra, Limbadri; Kong, Fandong; Liao, Shengrong; Yang, Bin; Zhou, Xuefeng; Wang, Junfeng; Liu, Yonghong; Organic Chemistry Frontiers 6 (2019) 3053–; doi:10.1039/C9QO00351G

data_1554874
_publ_section_title
;
 Phloroglucinol heterodimers and bis-indolyl alkaloids from the
 sponge-derived fungus Aspergillus sp. SCSIO 41018
;
_journal_issue                   17
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              3053
_journal_paper_doi               10.1039/C9QO00351G
_journal_volume                  6
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C23 H30 O8'
_chemical_formula_sum            'C23 H30 O8'
_chemical_formula_weight         434.47
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-07-09
_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                90
_cell_formula_units_Z            4
_cell_length_a                   8.00290(10)
_cell_length_b                   15.3468(3)
_cell_length_c                   17.8042(3)
_cell_measurement_reflns_used    6079
_cell_measurement_temperature    299.44(10)
_cell_measurement_theta_max      73.6560
_cell_measurement_theta_min      4.9720
_cell_volume                     2186.69(6)
_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      air
_diffrn_ambient_temperature      299.44(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.980
_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    -28.00   3.00   0.50    1.00    --    0.00 -82.00 -60.00   62
  2  \w    -26.00  18.00   0.50    1.00    --    0.00 -82.00-120.00   88
  3  \w    -33.00  23.00   0.50    1.00    --    0.00 -82.00  60.00  112
  4  \w     74.00 122.00   0.50    6.32    --   95.20  15.00 120.00   96
  5  \w    158.00 184.00   0.50    6.32    --   95.20  30.00 120.00   52
  6  \w    115.00 181.00   0.50    6.32    --   95.20  82.00  90.00  132
  7  \w      6.00 109.00   0.50    6.32    --   95.20 -45.00-180.00  206
  8  \w     91.00 116.00   0.50    6.32    --   95.20 -77.00 120.00   50
  9  \w      6.00  43.00   0.50    6.32    --   95.20 -77.00 120.00   74
 10  \w     94.00 120.00   0.50    6.32    --   95.20  30.00 120.00   52
 11  \w    135.00 172.00   0.50    6.32    --   95.20  15.00 120.00   74
 12  \w     92.00 184.00   0.50    6.32    --   95.20  15.00  30.00  184
 13  \w      7.00 104.00   0.50    6.32    --   95.20 -30.00-180.00  194
;
_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      0.0186018000
_diffrn_orient_matrix_UB_12      -0.0487441000
_diffrn_orient_matrix_UB_13      0.0751672000
_diffrn_orient_matrix_UB_21      0.1678811000
_diffrn_orient_matrix_UB_22      -0.0380590000
_diffrn_orient_matrix_UB_23      -0.0267396000
_diffrn_orient_matrix_UB_31      0.0922916000
_diffrn_orient_matrix_UB_32      0.0790825000
_diffrn_orient_matrix_UB_33      0.0335031000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0242
_diffrn_reflns_av_unetI/netI     0.0262
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            11698
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.482
_diffrn_reflns_theta_min         4.968
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.827
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82228
_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    1.320
_exptl_crystal_description       block
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.136
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details
;
 Flack x determined using 1599 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         4299
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0361
_refine_ls_R_factor_gt           0.0333
_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^)+(0.0509P)^2^+0.2256P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0883
_refine_ls_wR_factor_ref         0.0915
_reflns_Friedel_coverage         0.719
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.937
_reflns_number_gt                4025
_reflns_number_total             4299
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9qo00351g4.cif
_cod_data_source_block           guocui_4-9-2_collect
_cod_database_code               1554874
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C96 H124 O28 '
_shelx_estimated_absorpt_t_max   0.952
_shelx_estimated_absorpt_t_min   0.852
_reflns_odcompleteness_completeness 99.82
_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
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C9A(H9A), C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B)
2.c Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C17(H17A,H17B,H17C), C19(H19A,H19B,H19C), C22(H22A,H22B,
 H22C), C18(H18A,H18B,H18C), C21(H21A,H21B,H21C), C16(H16A,H16B,H16C), C15(H15A,
 H15B,H15C)
2.d Idealised tetrahedral OH refined as rotating group:
 O4(H4), O2(H2)
;
_shelx_res_checksum              23961
_shelx_hkl_checksum              10129
_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 1.292
_oxdiff_exptl_absorpt_empirical_full_min 0.666