Reisolation and Configurational Reinvestigation of Cottoquinazolines E-G from an Arthropod-Derived Strain of the Fungus <i>Neosartorya fischeri</i>.
Lin, Shuang; Yu, Huimin; Yang, Beiye; Li, Fengli; Chen, Xia; Li, Huaqiang; Zhang, Sitian; Wang, Jianping; Hu, Youcai; Hu, Zhengxi; Zhang, Yonghui; Journal of natural products 83 (2020) 169–173; doi:10.1021/acs.jnatprod.9b01000

data_1556983
_publ_section_title
;
 Reisolation and Configurational Reinvestigation of Cottoquinazolines E-G
 from an Arthropod-Derived Strain of the Fungus <i>Neosartorya
 fischeri</i>.
;
_journal_issue                   1
_journal_name_full               'Journal of natural products'
_journal_page_first              169
_journal_page_last               173
_journal_paper_doi               10.1021/acs.jnatprod.9b01000
_journal_volume                  83
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C23 H19 N5 O4, 0.17(H2 O1)'
_chemical_formula_sum            'C23 H19.35 N5 O4.18'
_chemical_formula_weight         432.58
_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             2019-01-16
_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            8
_cell_length_a                   7.43380(10)
_cell_length_b                   19.18740(10)
_cell_length_c                   28.72810(10)
_cell_measurement_reflns_used    68923
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.5970
_cell_measurement_theta_min      2.7800
_cell_volume                     4097.64(6)
_computing_cell_refinement       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.989
_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    -21.00  65.00   0.50    0.50    --    0.00  57.00-120.00  172
  2  \w    -15.00  47.00   0.50    0.50    --    0.00  19.00  60.00  124
  3  \w    -15.00  44.00   0.50    0.50    --    0.00  38.00   0.00  118
  4  \w    -18.00   8.00   0.50    0.50    --    0.00  19.00-120.00   52
  5  \w    -44.00  18.00   0.50    0.50    --    0.00 -19.00-180.00  124
  6  \w    -10.00  17.00   0.50    0.50    --    0.00  38.00-120.00   54
  7  \w     59.00  85.00   0.50    0.50    --    0.00  38.00   0.00   52
  8  \w    -21.00  56.00   0.50    0.50    --    0.00  57.00 -60.00  154
  9  \w     24.00  86.00   0.50    0.50    --    0.00  38.00-120.00  124
 10  \w     33.00  59.00   0.50    0.50    --    0.00  19.00-120.00   52
 11  \w    -17.00  89.00   0.50    0.50    --    0.00  38.00 150.00  212
 12  \w     69.00 178.00   0.50    1.20    --   94.60  68.00   3.51  218
 13  \w     71.00  96.00   0.50    1.20    --   94.60  60.00-128.75   50
 14  \w     66.00  91.00   0.50    1.20    --   94.60  74.00   4.92   50
 15  \w    105.00 133.00   0.50    1.20    --   94.60  71.00 -19.56   56
 16  \w     67.00  96.00   0.50    1.20    --   94.60  71.00 -19.56   58
 17  \w     70.00  96.00   0.50    1.20    --   94.60  64.00 -29.13   52
 18  \w     67.00  92.00   0.50    1.20    --   94.60  73.00  -9.67   50
 19  \w     67.00  93.00   0.50    1.20    --   94.60  71.00  62.24   52
 20  \w     70.00  96.00   0.50    1.20    --   94.60  67.00-126.70   52
 21  \w     71.00 107.00   0.50    1.20    --   94.60  59.00-157.79   72
 22  \w     67.00  92.00   0.50    1.20    --   94.60  73.00 142.15   50
 23  \w     66.00  93.00   0.50    1.20    --   94.60  74.00  28.21   54
 24  \w     67.00  93.00   0.50    1.20    --   94.60  73.00  83.05   52
 25  \w     68.00  94.00   0.50    1.20    --   94.60  70.00 -61.59   52
 26  \w    105.00 130.00   0.50    1.20    --   94.60  70.00 -61.59   50
 27  \w     66.00  92.00   0.50    1.20    --   94.60  75.00 -87.43   52
 28  \w     70.00 180.00   0.50    1.20    --   94.60  63.00  65.76  220
 29  \w     67.00  92.00   0.50    1.20    --   94.60  71.00 -44.62   50
 30  \w    117.00 144.00   0.50    1.20    --   94.60  71.00 -44.62   54
 31  \w     68.00  93.00   0.50    1.20    --   94.60  69.00  49.22   50
 32  \w     66.00  91.00   0.50    1.20    --   94.60  74.00 -72.20   50
 33  \w     72.00 184.00   0.50    1.20    --   94.60  55.00 -62.97  224
 34  \w     67.00  92.00   0.50    1.20    --   94.60  73.00-174.37   50
 35  \w     67.00 132.00   0.50    1.20    --   94.60  72.00 156.44  130
 36  \w     67.00 184.00   0.50    1.20    --   94.60  73.00 129.06  234
 37  \w     71.00  98.00   0.50    1.20    --   94.60  60.00-106.50   54
 38  \w     66.00  92.00   0.50    1.20    --   94.60  74.00  89.24   52
 39  \w     66.00  91.00   0.50    1.20    --   94.60  75.00 169.08   50
 40  \w    155.00 182.00   0.50    1.20    --   94.60  75.00 169.08   54
 41  \w     69.00  95.00   0.50    1.20    --   94.60  67.00  77.28   52
 42  \w     67.00  93.00   0.50    1.20    --   94.60  73.00 -34.10   52
 43  \w     70.00 101.00   0.50    1.20    --   94.60  64.00 129.44   62
 44  \w      8.00 118.00   0.50    1.20    --   94.60 -61.00-180.00  220
 45  \w      5.00 125.00   0.50    1.20    --   94.60 -82.00  30.00  240
 46  \w     11.00  41.00   0.50    1.20    --   94.60 -82.00-150.00   60
 47  \w     61.00 125.00   0.50    1.20    --   94.60 -82.00-150.00  128
 48  \w     48.00  94.00   0.50    1.20    --   94.60 -77.00 -60.00   92
 49  \w      6.00  52.00   0.50    1.20    --   94.60 -82.00  60.00   92
 50  \w     61.00 126.00   0.50    1.20    --   94.60 -82.00  60.00  130
 51  \w     67.00 177.00   0.50    1.20    --   94.60  71.00  19.57  220
 52  \w     67.00  93.00   0.50    1.20    --   94.60  71.00 -56.12   52
 53  \w     83.00 123.00   0.50    1.20    --   94.60 -82.00 -60.00   80
 54  \w     71.00  99.00   0.50    1.20    --   94.60  61.00   0.00   56
 55  \w    119.00 145.00   0.50    1.20    --   94.60  71.00 151.34   52
 56  \w     50.00 123.00   0.50    1.20    --   94.60 -82.00 120.00  146
 57  \w    158.00 183.00   0.50    1.20    --   94.60  74.00 102.10   50
 58  \w     71.00  97.00   0.50    1.20    --   94.60  61.00-180.00   52
 59  \w    103.00 140.00   0.50    1.20    --   94.60  61.00-180.00   74
 60  \w     71.00 175.00   0.50    1.20    --   94.60  61.00  90.00  208
 61  \w     69.00  94.00   0.50    1.20    --   94.60  68.00-146.91   50
 62  \w     66.00 147.00   0.50    1.20    --   94.60  74.00 102.10  162
 63  \w     98.00 123.00   0.50    1.20    --   94.60  75.00-165.03   50
 64  \w     71.00 178.00   0.50    1.20    --   94.60  59.00 -93.73  214
 65  \w    145.00 177.00   0.50    1.20    --   94.60  74.00-103.51   64
 66  \w     66.00  92.00   0.50    1.20    --   94.60  74.00-103.51   52
 67  \w     66.00  92.00   0.50    1.20    --   94.60  75.00-165.03   52
 68  \w     67.00  93.00   0.50    1.20    --   94.60  71.00 151.34   52
 69  \w    156.00 181.00   0.50    1.20    --   94.60  73.00  -9.67   50
 70  \w     71.00 183.00   0.50    1.20    --   94.60  59.00-149.71  224
 71  \w     71.00 179.00   0.50    1.20    --   94.60  62.00-125.46  216
;
_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      0.0194904000
_diffrn_orient_matrix_UB_12      0.0654073000
_diffrn_orient_matrix_UB_13      0.0306833000
_diffrn_orient_matrix_UB_21      -0.0258543000
_diffrn_orient_matrix_UB_22      -0.0449651000
_diffrn_orient_matrix_UB_23      0.0439002000
_diffrn_orient_matrix_UB_31      0.2047864000
_diffrn_orient_matrix_UB_32      -0.0118601000
_diffrn_orient_matrix_UB_33      0.0026523000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0396
_diffrn_reflns_av_unetI/netI     0.0161
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            109977
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.936
_diffrn_reflns_theta_min         2.769
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.823
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81589
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.28b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.402
_exptl_crystal_description       needle
_exptl_crystal_F_000             1806
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.113
_refine_diff_density_min         -0.162
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details
;
 Flack x determined using 3463 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     591
_refine_ls_number_reflns         8221
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0261
_refine_ls_R_factor_gt           0.0254
_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^)+(0.0361P)^2^+0.8102P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0650
_refine_ls_wR_factor_ref         0.0654
_reflns_Friedel_coverage         0.771
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.988
_reflns_number_gt                8060
_reflns_number_total             8221
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np9b01000_si_003.cif
_cod_data_source_block           20181214_ls1-29-18
_cod_depositor_comments
'Adding full bibliography for 1556983--1556984.cif.'
_cod_database_code               1556983
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.960
_shelx_estimated_absorpt_t_min   0.790
_reflns_odcompleteness_completeness 99.95
_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) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2. Others
 Fixed Sof: O1W(0.35) H1WA(0.35) H1WB(0.35)
3.a Riding coordinates:
 N19(H19), N19A(H19A)
3.b Free rotating group:
 O1W(H1WA,H1WB)
3.c Ternary CH refined with riding coordinates:
 C3(H3), C14(H14), C18(H18), C20(H20), C3A(H3A), C14A(H14A), C18A(H18A),
 C20A(H20A)
3.d Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C15A(H15C,H15D)
3.e Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C10(H10), C24(H24), C25(H25), C26(H26), C27(H27),
 N2(H2), C7A(H7A), C8A(H8A), C9A(H9A), C10A(H10A), C24A(H24A), C25A(H25A),
 C26A(H26A), C27A(H27A), N2A(H2A)
3.f Idealised Me refined as rotating group:
 C29(H29A,H29B,H29C), C29A(H29D,H29E,H29F)
;
_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 1.320
_oxdiff_exptl_absorpt_empirical_full_min 0.687