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#$Date: 2025-08-19 01:15:59 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301787 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/13/1561309.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1561309
loop_
_publ_author_name
'Xu, Wei-Feng'
'Chao, Rong'
'Hai, Yang'
'Guo, Yang-Yang'
'Wei, Mei-Yan'
'Wang, Chang-Yun'
'Shao, Chang-Lun'
_publ_section_title
;
 17-Hydroxybrevianamide N and Its N1-Methyl Derivative, Quinazolinones
 from a Soft-Coral-Derived Aspergillus sp. Fungus: 13S
 Enantiomers as the True Natural Products.
;
_journal_name_full               'Journal of natural products'
_journal_paper_doi               10.1021/acs.jnatprod.1c00098
_journal_year                    2021
_chemical_formula_sum            'C18 H13 N3 O4'
_chemical_formula_weight         335.31
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 131.76(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   24.705(4)
_cell_length_b                   8.3362(5)
_cell_length_c                   20.825(3)
_cell_measurement_temperature    293(2)
_cell_volume                     3199.2(17)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0264
_diffrn_reflns_av_sigmaI/netI    0.0418
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            6047
_diffrn_reflns_theta_full        67.21
_diffrn_reflns_theta_max         67.21
_diffrn_reflns_theta_min         4.36
_exptl_absorpt_coefficient_mu    0.841
_exptl_absorpt_correction_T_max  0.9132
_exptl_absorpt_correction_T_min  0.9059
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1392
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.11
_refine_diff_density_max         2.550
_refine_diff_density_min         -0.535
_refine_diff_density_rms         0.180
_refine_ls_extinction_coef       0.0010(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.711
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         2860
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.711
_refine_ls_R_factor_all          0.1595
_refine_ls_R_factor_gt           0.1284
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3730
_refine_ls_wR_factor_ref         0.4346
_reflns_number_gt                1968
_reflns_number_total             2860
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            np1c00098_si_002.cif
_cod_data_source_block           exp_10835
_cod_original_cell_volume        3199.4(7)
_cod_database_code               1561309
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.2523(3) -0.1552(5) 0.3210(3) 0.0412(12) Uani 1 1 d . . .
H1A H 0.2196 -0.2206 0.2817 0.049 Uiso 1 1 calc R . .
N2 N 0.3581(2) 0.1588(5) 0.3361(3) 0.0420(12) Uani 1 1 d . . .
N3 N 0.3715(2) 0.0326(5) 0.4470(3) 0.0383(12) Uani 1 1 d . . .
O1 O 0.2960(3) 0.3364(5) 0.4297(4) 0.0650(14) Uani 1 1 d . . .
H1 H 0.3190 0.3430 0.4815 0.097 Uiso 1 1 calc R . .
O2 O 0.2740(3) -0.3100(5) 0.4260(3) 0.0571(13) Uani 1 1 d . . .
O3 O 0.2273(2) 0.0116(5) 0.2204(3) 0.0566(13) Uani 1 1 d . . .
O4 O 0.4701(2) 0.0716(6) 0.5888(3) 0.0660(14) Uani 1 1 d . . .
C1 C 0.2336(3) 0.2597(7) 0.3912(4) 0.0495(16) Uani 1 1 d . . .
C2 C 0.1663(5) 0.3242(9) 0.3187(5) 0.068(2) Uani 1 1 d . . .
H2 H 0.1650 0.4229 0.2969 0.082 Uiso 1 1 calc R . .
C3 C 0.1012(4) 0.2419(13) 0.2789(6) 0.084(3) Uani 1 1 d . . .
H3 H 0.0572 0.2844 0.2305 0.101 Uiso 1 1 calc R . .
C4 C 0.1036(4) 0.1018(12) 0.3114(5) 0.076(2) Uani 1 1 d . . .
H4 H 0.0605 0.0480 0.2862 0.092 Uiso 1 1 calc R . .
C5 C 0.1673(4) 0.0360(9) 0.3805(5) 0.065(2) Uani 1 1 d . . .
H5 H 0.1667 -0.0635 0.4002 0.078 Uiso 1 1 calc R . .
C6 C 0.2347(3) 0.1124(6) 0.4237(4) 0.0407(13) Uani 1 1 d . . .
C7 C 0.3036(3) 0.0353(7) 0.4980(4) 0.0425(14) Uani 1 1 d . . .
H7A H 0.2942 -0.0324 0.5275 0.051 Uiso 1 1 calc R . .
H7B H 0.3373 0.1182 0.5380 0.051 Uiso 1 1 calc R . .
C8 C 0.3401(3) -0.0674(6) 0.4739(4) 0.0386(13) Uani 1 1 d . . .
H8 H 0.3803 -0.1257 0.5258 0.046 Uiso 1 1 calc R . .
C9 C 0.2876(3) -0.1909(6) 0.4070(4) 0.0420(14) Uani 1 1 d . . .
C10 C 0.2667(3) -0.0242(6) 0.2963(4) 0.0425(14) Uani 1 1 d . . .
C11 C 0.3351(3) 0.0645(6) 0.3620(3) 0.0355(12) Uani 1 1 d . . .
C12 C 0.4257(3) 0.2296(6) 0.3975(4) 0.0417(14) Uani 1 1 d . . .
C13 C 0.4523(4) 0.3292(7) 0.3689(5) 0.0569(18) Uani 1 1 d . . .
H13 H 0.4252 0.3477 0.3106 0.068 Uiso 1 1 calc R . .
C14 C 0.5209(4) 0.3991(8) 0.4316(6) 0.071(2) Uani 1 1 d . . .
H14 H 0.5390 0.4664 0.4141 0.085 Uiso 1 1 calc R . .
C15 C 0.5629(4) 0.3709(8) 0.5196(5) 0.0559(17) Uani 1 1 d . . .
H15 H 0.6083 0.4181 0.5600 0.067 Uiso 1 1 calc R . .
C16 C 0.5359(3) 0.2729(8) 0.5449(5) 0.0547(17) Uani 1 1 d . . .
H16 H 0.5638 0.2531 0.6032 0.066 Uiso 1 1 calc R . .
C17 C 0.4680(3) 0.2017(7) 0.4858(4) 0.0408(13) Uani 1 1 d . . .
C18 C 0.4383(3) 0.1017(7) 0.5119(4) 0.0435(14) Uani 1 1 d . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 N1 C9 124.0(5) . . ?
C11 N2 C12 118.1(5) . . ?
C11 N3 C18 120.5(5) . . ?
C11 N3 C8 122.6(4) . . ?
C18 N3 C8 116.8(5) . . ?
O1 C1 C6 119.2(5) . . ?
O1 C1 C2 121.8(6) . . ?
C6 C1 C2 119.0(6) . . ?
C3 C2 C1 121.0(7) . . ?
C4 C3 C2 118.9(7) . . ?
C3 C4 C5 121.4(8) . . ?
C4 C5 C6 122.6(7) . . ?
C1 C6 C5 117.0(6) . . ?
C1 C6 C7 121.8(5) . . ?
C5 C6 C7 121.2(5) . . ?
C6 C7 C8 114.4(4) . . ?
N3 C8 C9 112.4(4) . . ?
N3 C8 C7 112.1(4) . . ?
C9 C8 C7 110.4(4) . . ?
O2 C9 N1 121.6(5) . . ?
O2 C9 C8 121.4(5) . . ?
N1 C9 C8 117.0(4) . . ?
O3 C10 N1 120.4(5) . . ?
O3 C10 C11 120.6(5) . . ?
N1 C10 C11 118.7(5) . . ?
N2 C11 N3 124.7(5) . . ?
N2 C11 C10 118.1(5) . . ?
N3 C11 C10 117.2(4) . . ?
N2 C12 C17 121.7(5) . . ?
N2 C12 C13 118.2(6) . . ?
C17 C12 C13 120.1(6) . . ?
C14 C13 C12 117.7(7) . . ?
C15 C14 C13 122.1(6) . . ?
C16 C15 C14 118.7(6) . . ?
C15 C16 C17 121.9(7) . . ?
C16 C17 C12 119.6(6) . . ?
C16 C17 C18 122.3(6) . . ?
C12 C17 C18 118.0(5) . . ?
O4 C18 N3 119.2(5) . . ?
O4 C18 C17 123.9(5) . . ?
N3 C18 C17 116.9(5) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C10 1.351(7) . ?
N1 C9 1.407(7) . ?
N2 C11 1.280(7) . ?
N2 C12 1.389(7) . ?
N3 C11 1.376(7) . ?
N3 C18 1.383(7) . ?
N3 C8 1.479(6) . ?
O1 C1 1.336(8) . ?
O2 C9 1.195(6) . ?
O3 C10 1.220(7) . ?
O4 C18 1.254(7) . ?
C1 C6 1.393(8) . ?
C1 C2 1.410(9) . ?
C2 C3 1.402(12) . ?
C3 C4 1.332(13) . ?
C4 C5 1.354(11) . ?
C5 C6 1.411(9) . ?
C6 C7 1.482(8) . ?
C7 C8 1.550(7) . ?
C8 C9 1.508(8) . ?
C10 C11 1.482(8) . ?
C12 C17 1.403(8) . ?
C12 C13 1.412(8) . ?
C13 C14 1.404(10) . ?
C14 C15 1.398(10) . ?
C15 C16 1.362(9) . ?
C16 C17 1.390(8) . ?
C17 C18 1.433(8) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 164609933
