#------------------------------------------------------------------------------
#$Date: 2025-08-19 01:15:59 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301787 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/13/1561310.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_1561310
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            'C19 H17 N3 O5'
_chemical_formula_weight         367.35
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                95.446(6)
_cell_angle_beta                 105.411(6)
_cell_angle_gamma                114.671(7)
_cell_formula_units_Z            2
_cell_length_a                   8.3911(6)
_cell_length_b                   8.8058(7)
_cell_length_c                   13.4606(8)
_cell_measurement_reflns_used    1831
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.6800
_cell_measurement_theta_min      5.6880
_cell_volume                     846.93(13)
_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_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXL-2018/3 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0325
_diffrn_reflns_av_unetI/netI     0.0503
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5073
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.217
_diffrn_reflns_theta_max         67.217
_diffrn_reflns_theta_min         3.504
_diffrn_source                   'fine-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.887
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91551
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.440
_exptl_crystal_description       block
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.220
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         3018
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.220
_refine_ls_R_factor_all          0.0796
_refine_ls_R_factor_gt           0.0550
_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/[σ²(Fo²)+(0.0350P)²+0.4489P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1408
_refine_ls_wR_factor_ref         0.1512
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2173
_reflns_number_total             3018
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            np1c00098_si_003.cif
_cod_data_source_block           exp_11184
_cod_original_cell_volume        846.94(12)
_cod_database_code               1561310
_shelx_shelxl_version_number     2018/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.901
_shelx_estimated_absorpt_t_max   0.909
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.8131(3) 0.9473(3) 0.31664(18) 0.0347(6) Uani 1 1 d . . . . .
N2 N 0.6788(3) 0.9408(3) 0.45034(19) 0.0387(6) Uani 1 1 d . . . . .
N3 N 0.5370(3) 0.6063(3) 0.22115(19) 0.0386(6) Uani 1 1 d . . . . .
O1 O 0.5868(3) 1.1328(3) 0.25537(17) 0.0471(6) Uani 1 1 d . . . . .
H1 H 0.540583 1.163151 0.294792 0.071 Uiso 1 1 calc R U . . .
O2 O 0.6841(3) 0.5971(3) 0.10450(18) 0.0545(6) Uani 1 1 d . . . . .
O3 O 1.0825(3) 1.1702(3) 0.32231(18) 0.0537(6) Uani 1 1 d . . . . .
O4 O 0.4073(3) 0.6238(3) 0.3467(2) 0.0613(7) Uani 1 1 d . . . . .
O5 O 0.4773(3) 0.2637(3) 0.39945(18) 0.0565(7) Uani 1 1 d . . . . .
H5D H 0.361701 0.234468 0.374367 0.068 Uiso 1 1 d R U . . .
H5B H 0.500341 0.226848 0.454957 0.068 Uiso 1 1 d R U . . .
C1 C 0.4503(4) 0.9960(4) 0.1760(2) 0.0384(7) Uani 1 1 d . . . . .
C2 C 0.2630(5) 0.9463(4) 0.1581(3) 0.0487(8) Uani 1 1 d . . . . .
H2 H 0.228124 1.007260 0.200648 0.058 Uiso 1 1 calc R U . . .
C3 C 0.1277(5) 0.8062(5) 0.0770(3) 0.0571(9) Uani 1 1 d . . . . .
H3 H 0.002293 0.771963 0.066212 0.069 Uiso 1 1 calc R U . . .
C4 C 0.1784(5) 0.7178(4) 0.0126(3) 0.0532(9) Uani 1 1 d . . . . .
H4 H 0.087841 0.623957 -0.042042 0.064 Uiso 1 1 calc R U . . .
C5 C 0.3647(5) 0.7690(4) 0.0296(2) 0.0450(8) Uani 1 1 d . . . . .
H5 H 0.397998 0.709023 -0.014638 0.054 Uiso 1 1 calc R U . . .
C6 C 0.5044(4) 0.9079(4) 0.1110(2) 0.0374(7) Uani 1 1 d . . . . .
C7 C 0.7056(4) 0.9568(4) 0.1283(2) 0.0412(7) Uani 1 1 d . . . . .
H7A H 0.777862 1.080752 0.153315 0.049 Uiso 1 1 calc R U . . .
H7B H 0.718093 0.924991 0.060847 0.049 Uiso 1 1 calc R U . . .
C8 C 0.7883(4) 0.8721(4) 0.2084(2) 0.0385(7) Uani 1 1 d . . . . .
H8 H 0.911932 0.896962 0.205336 0.046 Uiso 1 1 calc R U . . .
C9 C 0.9663(4) 1.1088(4) 0.3652(2) 0.0392(7) Uani 1 1 d . . . . .
C10 C 0.9690(4) 1.1897(4) 0.4652(2) 0.0382(7) Uani 1 1 d . . . . .
C11 C 1.1116(4) 1.3529(4) 0.5216(3) 0.0458(8) Uani 1 1 d . . . . .
H11 H 1.208912 1.409643 0.496776 0.055 Uiso 1 1 calc R U . . .
C12 C 1.1073(5) 1.4288(4) 0.6137(3) 0.0521(9) Uani 1 1 d . . . . .
H12 H 1.202502 1.537214 0.651728 0.063 Uiso 1 1 calc R U . . .
C13 C 0.9618(5) 1.3452(5) 0.6508(3) 0.0549(9) Uani 1 1 d . . . . .
H13 H 0.960205 1.398458 0.713325 0.066 Uiso 1 1 calc R U . . .
C14 C 0.8205(5) 1.1850(4) 0.5964(3) 0.0475(8) Uani 1 1 d . . . . .
H14 H 0.723495 1.130197 0.621864 0.057 Uiso 1 1 calc R U . . .
C15 C 0.8226(4) 1.1043(4) 0.5027(2) 0.0378(7) Uani 1 1 d . . . . .
C16 C 0.6802(4) 0.8721(4) 0.3618(2) 0.0359(7) Uani 1 1 d . . . . .
C17 C 0.5282(4) 0.6918(4) 0.3095(2) 0.0407(7) Uani 1 1 d . . . . .
C18 C 0.6703(4) 0.6810(4) 0.1751(2) 0.0401(7) Uani 1 1 d . . . . .
C19 C 0.3966(5) 0.4260(4) 0.1728(3) 0.0561(9) Uani 1 1 d . . . . .
H19A H 0.339430 0.412817 0.098448 0.084 Uiso 1 1 calc R U . . .
H19B H 0.303167 0.394480 0.206134 0.084 Uiso 1 1 calc R U . . .
H19C H 0.455580 0.353016 0.182294 0.084 Uiso 1 1 calc R U . . .
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
C16 N1 C9 122.1(2) . . ?
C16 N1 C8 121.0(2) . . ?
C9 N1 C8 116.4(2) . . ?
C16 N2 C15 117.1(3) . . ?
C18 N3 C17 123.5(3) . . ?
C18 N3 C19 117.8(3) . . ?
C17 N3 C19 118.7(3) . . ?
O1 C1 C2 121.7(3) . . ?
O1 C1 C6 117.9(3) . . ?
C2 C1 C6 120.4(3) . . ?
C3 C2 C1 120.3(3) . . ?
C4 C3 C2 120.1(3) . . ?
C3 C4 C5 119.5(3) . . ?
C4 C5 C6 122.0(3) . . ?
C5 C6 C1 117.7(3) . . ?
C5 C6 C7 120.3(3) . . ?
C1 C6 C7 122.0(3) . . ?
C6 C7 C8 114.1(2) . . ?
N1 C8 C18 113.8(2) . . ?
N1 C8 C7 110.7(2) . . ?
C18 C8 C7 109.5(2) . . ?
O3 C9 N1 119.8(3) . . ?
O3 C9 C10 125.9(3) . . ?
N1 C9 C10 114.3(3) . . ?
C11 C10 C15 120.2(3) . . ?
C11 C10 C9 120.8(3) . . ?
C15 C10 C9 119.0(3) . . ?
C12 C11 C10 119.6(3) . . ?
C11 C12 C13 120.5(3) . . ?
C14 C13 C12 120.8(3) . . ?
C13 C14 C15 119.8(3) . . ?
N2 C15 C14 118.4(3) . . ?
N2 C15 C10 122.4(3) . . ?
C14 C15 C10 119.2(3) . . ?
N2 C16 N1 125.0(3) . . ?
N2 C16 C17 115.9(3) . . ?
N1 C16 C17 119.0(3) . . ?
O4 C17 N3 121.9(3) . . ?
O4 C17 C16 120.3(3) . . ?
N3 C17 C16 117.8(3) . . ?
O2 C18 N3 121.2(3) . . ?
O2 C18 C8 120.3(3) . . ?
N3 C18 C8 118.3(3) . . ?
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 C16 1.368(4) . ?
N1 C9 1.397(4) . ?
N1 C8 1.464(3) . ?
N2 C16 1.289(4) . ?
N2 C15 1.390(4) . ?
N3 C18 1.379(4) . ?
N3 C17 1.382(4) . ?
N3 C19 1.472(4) . ?
O1 C1 1.364(4) . ?
O2 C18 1.207(3) . ?
O3 C9 1.223(4) . ?
O4 C17 1.207(4) . ?
C1 C2 1.387(4) . ?
C1 C6 1.396(4) . ?
C2 C3 1.385(5) . ?
C3 C4 1.372(5) . ?
C4 C5 1.378(5) . ?
C5 C6 1.391(4) . ?
C6 C7 1.502(4) . ?
C7 C8 1.546(4) . ?
C8 C18 1.498(4) . ?
C9 C10 1.453(4) . ?
C10 C11 1.396(4) . ?
C10 C15 1.400(4) . ?
C11 C12 1.368(5) . ?
C12 C13 1.387(5) . ?
C13 C14 1.371(5) . ?
C14 C15 1.396(4) . ?
C16 C17 1.504(4) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168307364
