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_1554876
_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         'C29 H26 N2 O4, 0.5(H2 O)'
_chemical_formula_sum            'C29 H27 N2 O4.5'
_chemical_formula_weight         475.52
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2018-09-14
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 91.9220(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   14.30370(10)
_cell_length_b                   14.08450(10)
_cell_length_c                   23.7866(2)
_cell_measurement_reflns_used    17936
_cell_measurement_temperature    104(7)
_cell_measurement_theta_max      73.4570
_cell_measurement_theta_min      4.3970
_cell_volume                     4789.36(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      N~2~
_diffrn_ambient_temperature      104(7)
_diffrn_detector                 'Pilatus3R 200K-A'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.986
_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    -44.00 -17.00   0.50    0.50    --    0.00 -77.00-150.00   54
  2  \w    -16.00  58.00   0.50    0.50    --    0.00  38.00 -30.00  148
  3  \w    -16.00  45.00   0.50    0.50    --    0.00  38.00-150.00  122
  4  \w     27.00  54.00   0.50    0.50    --    0.00  38.00  30.00   54
  5  \w    -10.00  19.00   0.50    0.50    --    0.00 -57.00  60.00   58
  6  \w      0.00  29.00   0.50    0.50    --    0.00 -77.00   0.00   58
  7  \w    -45.00 -12.00   0.50    0.50    --    0.00 -77.00   0.00   66
  8  \w      2.00  27.00   0.50    0.50    --    0.00 -77.00-150.00   50
  9  \w    -16.00  20.00   0.50    0.50    --    0.00  38.00 -90.00   72
 10  \w     48.00  77.00   0.50    0.50    --    0.00  38.00 -90.00   58
 11  \w     71.00  97.00   0.50    2.00    --   95.20  63.00 -20.59   52
 12  \w    154.00 183.00   0.50    2.00    --   95.20  55.00  15.56   58
 13  \w     68.00  94.00   0.50    2.00    --   95.20  71.00-113.05   52
 14  \w    139.00 166.00   0.50    2.00    --   95.20  71.00-113.05   54
 15  \w     73.00 100.00   0.50    2.00    --   95.20  55.00  15.56   54
 16  \w     70.00  96.00   0.50    2.00    --   95.20  66.00 -79.97   52
 17  \w     70.00  97.00   0.50    2.00    --   95.20  69.00 -15.52   54
 18  \w     69.00 122.00   0.50    2.00    --   95.20  69.00-105.53  106
 19  \w     72.00  99.00   0.50    2.00    --   95.20  71.00 -35.90   54
 20  \w     67.00  94.00   0.50    2.00    --   95.20  75.00  -6.61   54
 21  \w    131.00 158.00   0.50    2.00    --   95.20  71.00 -35.90   54
 22  \w      7.00  61.00   0.50    2.00    --   95.20 -61.00-180.00  108
 23  \w      7.00 127.00   0.50    2.00    --   95.20 -82.00 -60.00  240
 24  \w     14.00 118.00   0.50    2.00    --   95.20 -61.00 -60.00  208
 25  \w     73.00  98.00   0.50    2.00    --   95.20  61.00 -60.00   50
 26  \w    158.00 183.00   0.50    2.00    --   95.20  61.00 -60.00   50
 27  \w     73.00 116.00   0.50    2.00    --   95.20  61.00-120.00   86
 28  \w     60.00 104.00   0.50    2.00    --   95.20 -82.00-120.00   88
 29  \w     73.00 100.00   0.50    2.00    --   95.20  57.00 -42.62   54
 30  \w     68.00  94.00   0.50    2.00    --   95.20  71.00 -38.52   52
 31  \w     68.00  94.00   0.50    2.00    --   95.20  71.00  43.15   52
 32  \w     70.00  96.00   0.50    2.00    --   95.20  68.00  20.54   52
 33  \w    160.00 185.00   0.50    2.00    --   95.20  52.00  27.79   50
 34  \w     72.00 184.00   0.50    2.00    --   95.20  15.00 -60.00  224
 35  \w     77.00 143.00   0.50    2.00    --   95.20  45.00 -60.00  132
 36  \w     71.00  98.00   0.50    2.00    --   95.20  68.00 -52.69   54
 37  \w     73.00  98.00   0.50    2.00    --   95.20  61.00 -90.00   50
 38  \w     72.00  99.00   0.50    2.00    --   95.20  61.00 -30.00   54
 39  \w     74.00 101.00   0.50    2.00    --   95.20  61.00   0.00   54
 40  \w     68.00  94.00   0.50    2.00    --   95.20  71.00 -24.57   52
 41  \w     74.00 101.00   0.50    2.00    --   95.20  52.00  27.79   54
 42  \w     80.00 184.00   0.50    2.00    --   95.20  30.00   0.00  208
 43  \w     80.00 105.00   0.50    2.00    --   95.20  45.00 -30.00   50
 44  \w     76.00 165.00   0.50    2.00    --   95.20  45.00  30.00  178
 45  \w    132.00 157.00   0.50    2.00    --   95.20  69.00 -15.52   50
 46  \w    141.00 166.00   0.50    2.00    --   95.20  57.00  -4.11   50
 47  \w     78.00 107.00   0.50    2.00    --   95.20 -61.00-180.00   58
 48  \w     73.00 118.00   0.50    2.00    --   95.20  57.00  -4.11   90
;
_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      -0.1065155000
_diffrn_orient_matrix_UB_12      -0.0107064000
_diffrn_orient_matrix_UB_13      -0.0095833000
_diffrn_orient_matrix_UB_21      0.0115702000
_diffrn_orient_matrix_UB_22      0.0085840000
_diffrn_orient_matrix_UB_23      -0.0639639000
_diffrn_orient_matrix_UB_31      0.0114165000
_diffrn_orient_matrix_UB_32      -0.1085139000
_diffrn_orient_matrix_UB_33      -0.0041734000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0386
_diffrn_reflns_av_unetI/netI     0.0376
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            33163
_diffrn_reflns_point_group_measured_fraction_full 0.900
_diffrn_reflns_point_group_measured_fraction_max 0.872
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.153
_diffrn_reflns_theta_min         3.719
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'MicroMax 007 (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.725
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80630
_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 blackish black'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   blackish
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_description       block
_exptl_crystal_F_000             2008
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.414
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details
;
 Flack x determined using 3328 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.10(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     667
_refine_ls_number_reflns         8517
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0433
_refine_ls_R_factor_gt           0.0414
_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^)+(0.0750P)^2^+1.7101P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1125
_refine_ls_wR_factor_ref         0.1141
_reflns_Friedel_coverage         0.768
_reflns_Friedel_fraction_full    0.801
_reflns_Friedel_fraction_max     0.759
_reflns_number_gt                8150
_reflns_number_total             8517
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9qo00351g3.cif
_cod_data_source_block           guocui_4-14-2_collect
_cod_depositor_comments
;

2022-05-06
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_moiety     '2(C29 H26 N2 O4), H2 O'
_cod_original_formula_sum        'C58 H54 N4 O9'
_cod_original_formula_units_Z    4
_cod_original_formula_weight     951.05
_cod_database_code               1554876
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.951
_shelx_estimated_absorpt_t_min   0.869
_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 N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2. Restrained distances
 C12A-H12B
 1.023 with sigma of 0.02
3.a Free rotating group:
 O0AA(H0AA,H0AB)
3.b Aromatic/amide H refined with riding coordinates:
 N1"(H1"), N1A"(H1A"), N1A'(H1A'), N1'(H1'), C2A'(H2A'), C2'(H2'), C5A'(H5A'),
 C6A'(H6A'), C7A'(H7A'), C4A"(H4A"), C4A'(H4A'), C5A"(H5A"), C4'(H4'),
 C7A"(H7A"), C4"(H4"), C7'(H7'), C5"(H5"), C7"(H7"), C5'(H5'), C6"(H6"),
 C6A"(H6A"), C11A(H11A), C6'(H6'), C11"(H11")
3.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C7A(H7AA,H7AB,H7AC), C8(H8A,H8B,H8C), C13"(H13D,H13E,H13F),
 C14A(H14A,H14B,H14C), C8A(H8AA,H8AB,H8AC), C13A(H13A,H13B,H13C), C14"(H14D,
 H14E,H14F)
;
_shelx_res_checksum              63897
_shelx_hkl_checksum              5460
_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 1.568
_oxdiff_exptl_absorpt_empirical_full_min 0.593