Discovery of brevijanazines from Aspergillus brevijanus reveals the molecular basis for p-nitrobenzoic acid in fungi
Li, Hang; Mirzayans, Paul; Butler, Mark Stuart; Lacey, Alastair E.; Vuong, Daniel; Chen, Rachel; Kalaitzis, John A.; Moggach, Stephen A.; Lacey, Ernest; Piggott, Andrew M.; Chooi, Yit-Heng; Chemical Communications  (2022) –; doi:10.1039/D2CC01679F

data_7130054
_publ_section_title
;
 Discovery of brevijanazines from Aspergillus brevijanus reveals the
 molecular basis for p-nitrobenzoic acid in fungi
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC01679F
_journal_year                    2022
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C24 H28 N4 O6'
_chemical_formula_sum            'C24 H28 N4 O6'
_chemical_formula_weight         468.50
_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             2020-12-18
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_audit_update_record
;
2022-01-10 deposited with the CCDC.	2022-05-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.40330(10)
_cell_length_b                   12.51500(10)
_cell_length_c                   16.42590(10)
_cell_measurement_reflns_used    24580
_cell_measurement_temperature    99.9(5)
_cell_measurement_theta_max      75.1960
_cell_measurement_theta_min      4.4600
_cell_volume                     2344.18(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.9(5)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_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    -54.00  26.00   0.50    0.05    --  -46.20  48.00 121.00  160
  2  \w     79.00 175.00   0.50    0.20    --  102.41  86.00 -26.00  192
  3  \w     89.00 175.00   0.50    0.20    --  102.41  48.00 121.00  172
  4  \w     30.00 106.00   0.50    0.20    --  102.41 -93.00 116.00  152
  5  \w   -118.00 -73.00   0.50    0.05    --  -46.20-125.00  30.00   90
  6  \w   -118.00 -73.00   0.50    0.05    --  -46.20-125.00 150.00   90
  7  \w   -118.00 -33.00   0.50    0.05    --  -46.20 -48.00 -25.00  170
  8  \w    -28.00  26.00   0.50    0.05    --   46.20 -19.00-180.00  108
  9  \w   -111.00 -30.00   0.50    0.20    -- -102.41 125.00  30.00  162
 10  \w    -71.00 -30.00   0.50    0.20    -- -102.41  61.00 -30.00   82
 11  \w   -129.00 -30.00   0.50    0.20    -- -102.41  86.00 -26.00  198
 12  \w   -111.00 -30.00   0.50    0.20    -- -102.41 125.00   0.00  162
 13  \w     30.00  71.00   0.50    0.20    --  102.41 -61.00 150.00   82
 14  \w     30.00  71.00   0.50    0.20    --  102.41 -61.00 120.00   82
 15  \w     90.00 177.00   0.50    0.20    --  102.41  30.00 -60.00  174
 16  \w     30.00 105.00   0.50    0.20    --  102.41 -77.00   0.00  150
 17  \w     30.00  71.00   0.50    0.20    --  102.41 -61.00-150.00   82
 18  \w     30.00 105.00   0.50    0.20    --  102.41 -77.00-150.00  150
 19  \w     90.00 174.00   0.50    0.20    --  102.41  45.00-120.00  168
 20  \w   -118.00 -31.00   0.50    0.05    --  -46.20 -57.00 120.00  174
 21  \w   -118.00 -23.00   0.50    0.05    --  -46.20 -77.00  90.00  190
 22  \w   -118.00 -31.00   0.50    0.05    --  -46.20 -57.00-180.00  174
 23  \w   -118.00 -23.00   0.50    0.05    --  -46.20 -77.00 -90.00  190
 24  \w    -28.00  26.00   0.50    0.05    --   46.20 -19.00 -30.00  108
 25  \w     90.00 177.00   0.50    0.20    --  102.41  30.00-180.00  174
 26  \w     80.00 175.00   0.50    0.20    --  102.41  77.00 150.00  190
 27  \w     90.00 174.00   0.50    0.20    --  102.41  45.00  60.00  168
 28  \w     90.00 174.00   0.50    0.20    --  102.41  45.00 -30.00  168
 29  \w     86.00 175.00   0.50    0.20    --  102.41  61.00-180.00  178
 30  \w     90.00 174.00   0.50    0.20    --  102.41  45.00-150.00  168
 31  \w     80.00 175.00   0.50    0.20    --  102.41  77.00 -90.00  190
 32  \w     80.00 175.00   0.50    0.20    --  102.41  77.00-120.00  190
 33  \w     30.00 111.00   0.50    0.20    --  102.41-125.00-150.00  162
 34  \w     80.00 175.00   0.50    0.20    --  102.41  77.00 -30.00  190
 35  \w     90.00 174.00   0.50    0.20    --  102.41  45.00  90.00  168
 36  \w     86.00 175.00   0.50    0.20    --  102.41  61.00  30.00  178
 37  \w     30.00 111.00   0.50    0.20    --  102.41-125.00 -30.00  162
 38  \w     80.00 175.00   0.50    0.20    --  102.41  77.00 120.00  190
 39  \w     90.00 174.00   0.50    0.20    --  102.41  45.00  30.00  168
 40  \w   -118.00 -23.00   0.50    0.05    --  -46.20 -77.00 -30.00  190
 41  \w    -94.00 -13.00   0.50    0.05    --  -46.20 125.00 -60.00  162
 42  \w     24.00 118.00   0.50    0.05    --   46.20  77.00  30.00  188
 43  \w     24.00  57.00   0.50    0.05    --   46.20  77.00-150.00   66
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1236527000
_diffrn_orient_matrix_UB_12      -0.0082529000
_diffrn_orient_matrix_UB_13      0.0373444000
_diffrn_orient_matrix_UB_21      0.0172663000
_diffrn_orient_matrix_UB_22      0.1092832000
_diffrn_orient_matrix_UB_23      0.0415820000
_diffrn_orient_matrix_UB_31      -0.0516991000
_diffrn_orient_matrix_UB_32      0.0559886000
_diffrn_orient_matrix_UB_33      -0.0753149000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0896
_diffrn_reflns_av_unetI/netI     0.0327
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            54321
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.673
_diffrn_reflns_theta_min         4.442
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.801
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.34771
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_description       block
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.233
_exptl_crystal_size_mid          0.122
_exptl_crystal_size_min          0.096
_refine_diff_density_max         0.174
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details
;
 Flack x determined using 1999 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.12(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     311
_refine_ls_number_reflns         4852
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0341
_refine_ls_R_factor_gt           0.0330
_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^)+(0.0464P)^2^+0.4727P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0845
_refine_ls_wR_factor_ref         0.0856
_reflns_Friedel_coverage         0.760
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.987
_reflns_number_gt                4695
_reflns_number_total             4852
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc01679f2.cif
_cod_data_source_block           uuz7z
_cod_database_code               7130054
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'N4 O4 C26 H30'
_chemical_oxdiff_usercomment     'Hang for Heng'
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_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
2.a Ternary CH refined with riding coordinates:
 C00F(H00F), C00N(H00N), C00P(H00P), C00T(H00T)
2.b Secondary CH2 refined with riding coordinates:
 C00G(H00A,H00B), C00L(H00C,H00D)
2.c Aromatic/amide H refined with riding coordinates:
 C00H(H00H), C00J(H00J), C00K(H00K), C00M(H00M), C00O(H00O), C00R(H00R),
 C00S(H00S), C00U(H00U)
2.d Idealised Me refined as rotating group:
 C00V(H00E,H00G,H00I), C00W(H00L,H00Q,H00V), C00X(H00W,H00X,H00Y), C00Y(H00Z,H,
 HA)
;
_shelx_res_checksum              39830
_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 1.843
_oxdiff_exptl_absorpt_empirical_full_min 0.466