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_1554879
_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         'C28 H39 N O9, 1/3(C H4 O)'
_chemical_formula_sum            'C28.33333 H40.33333 N O9.33333'
_chemical_formula_weight         543.61
_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     direct
_audit_creation_date             2018-09-04
_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            12
_cell_length_a                   8.09067(8)
_cell_length_b                   25.4976(3)
_cell_length_c                   41.3088(4)
_cell_measurement_reflns_used    47077
_cell_measurement_temperature    101(2)
_cell_measurement_theta_max      73.5230
_cell_measurement_theta_min      4.0820
_cell_volume                     8521.70(15)
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      101(2)
_diffrn_detector                 'Pilatus3R 200K-A'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.993
_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     -5.00  25.00   0.50    6.00    --    0.00 -82.00  90.00   60
  2  \w    -87.00 -38.00   0.50    6.00    --    0.00 -38.00 120.00   98
  3  \w    -33.00  14.00   0.50    6.00    --    0.00 -77.00  60.00   94
  4  \w     10.00  79.00   0.50    6.00    --    0.00  57.00  60.00  138
  5  \w    -32.00  28.00   0.50    6.00    --    0.00 -82.00 -90.00  120
  6  \w    -17.00  29.00   0.50    6.00    --    0.00 -82.00 120.00   92
  7  \w     18.00 117.00   0.50   30.10    --   94.60 -61.00 -30.00  198
  8  \w    101.00 184.00   0.50   30.10    --   94.60  82.00 -30.00  166
  9  \w     45.00  74.00   0.50   30.10    --   94.60 -82.00 -90.00   58
 10  \w     31.00 124.00   0.50   30.10    --   94.60 -82.00  60.00  186
 11  \w      7.00 126.00   0.50   30.10    --   94.60 -82.00-167.00  238
 12  \w     47.00 123.00   0.50   30.10    --   94.60 -77.00 -30.00  152
 13  \w     42.00  68.00   0.50   30.10    --   94.60 -82.00 -60.00   52
 14  \w     78.00 103.00   0.50   30.10    --   94.60 -82.00 -60.00   50
 15  \w     71.00 127.00   0.50   30.10    --   94.60  61.00   0.00  112
 16  \w     72.00 178.00   0.50   30.10    --   94.60  61.00  60.00  212
 17  \w      8.00  34.00   0.50   30.10    --   94.60 -82.00 150.00   52
 18  \w     75.00 183.00   0.50   30.10    --   94.60  45.00-180.00  216
 19  \w     78.00 103.00   0.50   30.10    --   94.60 -82.00 150.00   50
 20  \w     58.00 110.00   0.50   30.10    --   94.60 -61.00  60.00  104
 21  \w     75.00 180.00   0.50   30.10    --   94.60  45.00 -90.00  210
 22  \w     93.00 154.00   0.50   30.10    --   94.60  77.00  30.00  122
 23  \w     86.00 114.00   0.50   30.10    --   94.60 -82.00 120.00   56
 24  \w     11.00  36.00   0.50   30.10    --   94.60 -77.00 -30.00   50
 25  \w     89.00 114.00   0.50   30.10    --   94.60 -82.00 -90.00   50
 26  \w     15.00  42.00   0.50   30.10    --   94.60 -82.00 -90.00   54
;
_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      -0.0621488000
_diffrn_orient_matrix_UB_12      0.0550720000
_diffrn_orient_matrix_UB_13      0.0093507000
_diffrn_orient_matrix_UB_21      -0.0765579000
_diffrn_orient_matrix_UB_22      -0.0225963000
_diffrn_orient_matrix_UB_23      0.0311741000
_diffrn_orient_matrix_UB_31      0.1628549000
_diffrn_orient_matrix_UB_32      0.0104410000
_diffrn_orient_matrix_UB_33      0.0182058000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0651
_diffrn_reflns_av_unetI/netI     0.0385
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       50
_diffrn_reflns_limit_l_min       -50
_diffrn_reflns_number            96685
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.827
_diffrn_reflns_theta_min         3.628
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.786
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56140
_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    1.271
_exptl_crystal_description       needle
_exptl_crystal_F_000             3496
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.182
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details
;
 Flack x determined using 6362 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1085
_refine_ls_number_reflns         17002
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0426
_refine_ls_R_factor_gt           0.0370
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0483P)^2^+2.1666P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0941
_refine_ls_wR_factor_ref         0.0974
_reflns_Friedel_coverage         0.789
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.977
_reflns_number_gt                15448
_reflns_number_total             17002
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9qo00351g5.cif
_cod_data_source_block           guocui_4-13-3_collect
_cod_depositor_comments
;

2022-05-28
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C85 H119 N3 O28'
_cod_original_formula_weight         1630.82
_cod_original_formula_moiety         '3(C28 H39 N O9), C H4 O'
_cod_original_formula_units_Z            4
_cod_original_cell_volume        8521.69(15)
_cod_database_code               1554879
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.969
_shelx_estimated_absorpt_t_min   0.798
_reflns_odcompleteness_completeness 99.92
_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 N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Rigid bond restraints
 N1, C11
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.001
3.a Ternary CH refined with riding coordinates:
 C20(H20), C20'(H20'), C15'(H15'), C15(H15), C20A(H20A), C15A(H15A)
3.b Secondary CH2 refined with riding coordinates:
 C16(H16E,H16F), C21A(H21A,H21B), C7'(H7'A,H7'B), C7(H7A,H7B), C21'(H21C,H21D),
  C7A(H7AA,H7AB), C16'(H16C,H16D), C21(H21E,H21F), C16A(H16A,H16B)
3.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C6'(H6'), C6A(H6A)
3.d X=CH2 refined with riding coordinates:
 N1'(H1'A,H1'B), N1(H1A,H1B)
3.e Idealised Me refined as rotating group:
 C24'(H24D,H24E,H24F), C25A(H25A,H25B,H25C), C26A(H26A,H26B,H26C), C24(H24G,
 H24H,H24I), C25(H25G,H25H,H25I), C23(H23G,H23H,H23I), C17A(H17A,H17B,H17C),
 C23A(H23A,H23B,H23C), C26(H26G,H26H,H26I), C26'(H26D,H26E,H26F), C18A(H18A,
 H18B,H18C), C18'(H18D,H18E,H18F), C27A(H27A,H27B,H27C), C22(H22G,H22H,H22I),
 C27(H27G,H27H,H27I), C28A(H28A,H28B,H28C), C28'(H28D,H28E,H28F), C17'(H17D,
 H17E,H17F), C116(H11A,H11B,H11C), C28(H28G,H28H,H28I), C17(H17G,H17H,H17I),
 C25'(H25D,H25E,H25F), C22'(H22D,H22E,H22F), C24A(H24A,H24B,H24C), C18(H18G,
 H18H,H18I), C23'(H23D,H23E,H23F), C27'(H27D,H27E,H27F), C22A(H22A,H22B,H22C)
3.f Idealised tetrahedral OH refined as rotating group:
 O8'(H8'), O8A(H8A), O8(H8), O115(H115)
;
_shelx_res_checksum              99529
_shelx_hkl_checksum              14300
_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 2.406
_oxdiff_exptl_absorpt_empirical_full_min 0.393