Quinazoline-Containing Indole Alkaloids from the Marine-Derived Fungus <i>Aspergillus</i> sp. HNMF114.
Kong, Fan-Dong; Zhang, Sheng-Liang; Zhou, Shuang-Qing; Ma, Qing-Yun; Xie, Qing-Yi; Chen, Jin-Ping; Li, Jiu-Hui; Zhou, Li-Man; Yuan, Jing-Zhe; Hu, Zhong; Dai, Hao-Fu; Huang, Xiao-Long; Zhao, You-Xing; Journal of natural products 82 (2019) 3456–3463; doi:10.1021/acs.jnatprod.9b00845

data_1556575
_publ_section_title
;
 Quinazoline-Containing Indole Alkaloids from the Marine-Derived Fungus
 <i>Aspergillus</i> sp. HNMF114.
;
_journal_issue                   12
_journal_name_full               'Journal of natural products'
_journal_page_first              3456
_journal_page_last               3463
_journal_paper_doi               10.1021/acs.jnatprod.9b00845
_journal_volume                  82
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C28 H30 N4 O7 S'
_chemical_formula_sum            'C28 H30 N4 O7 S'
_chemical_formula_weight         566.62
_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
_audit_creation_date             2019-07-15
_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                   8.73600(15)
_cell_length_b                   16.3578(3)
_cell_length_c                   18.2142(3)
_cell_measurement_reflns_used    5859
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      73.3350
_cell_measurement_theta_min      3.6000
_cell_volume                     2602.84(8)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_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      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.965
_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   -115.00 -16.00   1.00    1.00    --  -40.98 -38.00  30.00   99
  2  \w   -115.00 -16.00   1.00    1.00    --  -40.98 -38.00 120.00   99
  3  \w      1.00  82.00   1.00    1.00    --   40.98 -99.00 -90.00   81
  4  \w     35.00 136.00   1.00    3.18    --  106.95 -61.00-180.00  101
  5  \w     31.00 135.00   1.00    3.18    --  106.95 -30.00-120.00  104
  6  \w     25.00 109.00   1.00    3.18    --  106.95 -95.00  60.00   84
  7  \w     34.00  66.00   1.00    3.18    --  106.95 -45.00 -60.00   32
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0013904000
_diffrn_orient_matrix_UB_12      0.0366162000
_diffrn_orient_matrix_UB_13      -0.0779281000
_diffrn_orient_matrix_UB_21      -0.0074107000
_diffrn_orient_matrix_UB_22      -0.0867083000
_diffrn_orient_matrix_UB_23      -0.0330117000
_diffrn_orient_matrix_UB_31      -0.1760306000
_diffrn_orient_matrix_UB_32      0.0038464000
_diffrn_orient_matrix_UB_33      0.0007141000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0267
_diffrn_reflns_av_unetI/netI     0.0347
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            8966
_diffrn_reflns_point_group_measured_fraction_full 0.918
_diffrn_reflns_point_group_measured_fraction_max 0.876
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.586
_diffrn_reflns_theta_min         3.632
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.587
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77607
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.446
_exptl_crystal_description       block
_exptl_crystal_F_000             1192
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.194
_refine_diff_density_min         -0.366
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details
;
 Flack x determined using 1619 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.002(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     367
_refine_ls_number_reflns         4597
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0318
_refine_ls_R_factor_gt           0.0302
_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^)+(0.0403P)^2^+0.4537P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0752
_refine_ls_wR_factor_ref         0.0767
_reflns_Friedel_coverage         0.602
_reflns_Friedel_fraction_full    0.821
_reflns_Friedel_fraction_max     0.761
_reflns_number_gt                4417
_reflns_number_total             4597
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np9b00845_si_002.cif
_cod_data_source_block           22-6
_cod_depositor_comments          'Adding full bibliography for 1556575.cif.'
_cod_database_code               1556575
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.10
_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:
 C13(H13), C9(H9), C25(H25), C26(H26)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 C20(H20), C18(H18), C21(H21), C19(H19), C2(H2), C5(H5), C3(H3), C4(H4)
2.d Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C27(H27A,H27B,H27C), C22(H22A,H22B,H22C), C24(H24A,H24B,
 H24C), C28(H28A,H28B,H28C)
2.e Idealised tetrahedral OH refined as rotating group:
 O7(H7)
;
_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 1.321
_oxdiff_exptl_absorpt_empirical_full_min 0.726