#------------------------------------------------------------------------------
#$Date: 2025-08-19 00:06:14 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301780 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/26/1552679.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_1552679
loop_
_publ_author_name
'da Silva, Alison B.'
'Silveira, Edilberto R.'
'Wilke, Diego V.'
'Ferreira, Elhton G.'
'Costa-Lotufo, Leticia V'
'Torres, Maria Conceição M'
'Ayala, Alejandro Pedro'
'Costa, Wendell S.'
'Canuto, Kirley M.'
'de Araújo-Nobre, Alyne R'
'Araújo, Ana Jérsia'
'Filho, José Delano B Marinho'
'Pessoa, Otilia Deusdenia L.'
_publ_section_title
;
 Antibacterial Salinaphthoquinones from a Strain of the Bacterium
 Salinispora arenicola Recovered from the Marine Sediments of St.
 Peter and St. Paul Archipelago, Brazil.
;
_journal_issue                   7
_journal_name_full               'Journal of natural products'
_journal_page_first              1831
_journal_page_last               1838
_journal_paper_doi               10.1021/acs.jnatprod.9b00062
_journal_volume                  82
_journal_year                    2019
_chemical_formula_moiety         'C18 H15 N O5'
_chemical_formula_sum            'C18 H15 N O5'
_chemical_formula_weight         325.31
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-04-29
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.18 svn.r3508 for OlexSys, GUI svn.r5497)
;
_cell_angle_alpha                90
_cell_angle_beta                 108.007(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.8289(6)
_cell_length_b                   6.8772(3)
_cell_length_c                   16.9481(7)
_cell_measurement_reflns_used    8642
_cell_measurement_temperature    301(2)
_cell_measurement_theta_max      30.51
_cell_measurement_theta_min      2.52
_cell_volume                     1532.88(11)
_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    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      300.78
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0380
_diffrn_reflns_av_unetI/netI     0.0242
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            23319
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.280
_diffrn_reflns_theta_min         2.527
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_correction_T_min  0.618
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.'
_exptl_crystal_colour            'clear orangish orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   orangish
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_description       prism
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.836
_exptl_crystal_size_mid          0.276
_exptl_crystal_size_min          0.084
_refine_diff_density_max         0.206
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3792
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0624
_refine_ls_R_factor_gt           0.0444
_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/[σ²(Fo²)+(0.0532P)²+0.6159P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1132
_refine_ls_wR_factor_ref         0.1285
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2890
_reflns_number_total             3792
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            np9b00062_si_002.cif
_cod_data_source_block           bra213a6acd1
_cod_database_code               1552679
_shelx_shelxl_version_number     2016/6
_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_max   0.991
_shelx_estimated_absorpt_t_min   0.918
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H3(0.071) H1A(0.072) H8(0.04) H3A(0.05) H14(0.048) H11A(0.077)
 H11B(0.077) H11C(0.077) H17A(0.097) H17B(0.097) H18A(0.08) H18B(0.08)
 H18C(0.08)
 Fixed X: H3(0.114035) H1A(0.620254) H8(0.419544) H3A(0.485703) H14(0.072975)
 H11A(0.195711) H11B(0.250744) H11C(0.310099) H18A(0.253262) H18B(0.180481)
 H18C(0.278195)
 Fixed Y: H3(0.670612) H1A(0.078736) H8(0.308495) H3A(0.261015) H14(0.92127)
 H11A(0.409852) H11B(0.611612) H11C(0.420322) H18A(0.906414) H18B(1.048771)
 H18C(0.968603)
 Fixed Z: H3(0.413023) H1A(0.35161) H8(0.581044) H3A(0.266275) H14(0.177031)
 H11A(0.599624) H11B(0.618942) H11C(0.654147) H18A(0.37845) H18B(0.315043)
 H18C(0.297878)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
O4 O 0.12858(8) 0.43082(16) 0.25903(7) 0.0368(3) Uani 1 1 d .
O1 O 0.55977(9) 0.17753(17) 0.53097(7) 0.0415(3) Uani 1 1 d .
O3 O 0.14913(9) 0.6406(2) 0.45997(7) 0.0472(3) Uani 1 1 d .
H3 H 0.114035 0.670612 0.413023 0.071 Uiso 1 1 calc GR
O2 O 0.32905(10) 0.4709(2) 0.24286(7) 0.0506(3) Uani 1 1 d .
O5 O 0.01865(10) 0.3019(2) 0.14923(8) 0.0557(4) Uani 1 1 d .
N1 N 0.61121(12) 0.0959(2) 0.39669(11) 0.0483(4) Uani 1 1 d .
H1A H 0.620254 0.078736 0.351610 0.072 Uiso 1 1 calc GR
C7 C 0.29113(12) 0.4586(2) 0.53104(9) 0.0355(3) Uani 1 1 d .
C8 C 0.37828(12) 0.3608(2) 0.53146(9) 0.0330(3) Uani 1 1 d .
H8 H 0.419544 0.308495 0.581044 0.040 Uiso 1 1 calc R
C6 C 0.23162(11) 0.5405(2) 0.45581(9) 0.0335(3) Uani 1 1 d .
C4 C 0.37837(12) 0.3920(2) 0.30821(9) 0.0360(3) Uani 1 1 d .
C10 C 0.34499(11) 0.4138(2) 0.38426(9) 0.0302(3) Uani 1 1 d .
C5 C 0.25591(11) 0.5152(2) 0.38190(9) 0.0306(3) Uani 1 1 d .
C12 C 0.18301(11) 0.5846(2) 0.30302(9) 0.0321(3) Uani 1 1 d .
C9 C 0.40649(11) 0.3380(2) 0.45976(9) 0.0305(3) Uani 1 1 d .
C2 C 0.52704(12) 0.2017(2) 0.38632(10) 0.0371(3) Uani 1 1 d .
C1 C 0.50157(12) 0.2356(2) 0.46551(9) 0.0332(3) Uani 1 1 d .
C16 C 0.05795(12) 0.4518(3) 0.18257(10) 0.0392(4) Uani 1 1 d .
C3 C 0.46754(13) 0.2805(3) 0.31413(10) 0.0414(4) Uani 1 1 d .
H3A H 0.485703 0.261015 0.266275 0.050 Uiso 1 1 calc R
C13 C 0.16482(12) 0.7682(2) 0.27531(10) 0.0369(3) Uani 1 1 d .
C14 C 0.08798(13) 0.7953(3) 0.19699(10) 0.0402(4) Uani 1 1 d .
H14 H 0.072975 0.921270 0.177031 0.048 Uiso 1 1 calc R
C15 C 0.03649(13) 0.6471(3) 0.15092(10) 0.0416(4) Uani 1 1 d .
C11 C 0.25901(15) 0.4767(3) 0.60790(11) 0.0515(5) Uani 1 1 d .
H11A H 0.195711 0.409852 0.599624 0.077 Uiso 1 1 calc GR
H11B H 0.250744 0.611612 0.618942 0.077 Uiso 1 1 calc GR
H11C H 0.310099 0.420322 0.654147 0.077 Uiso 1 1 calc GR
C17 C -0.0426(2) 0.6736(4) 0.06807(13) 0.0646(6) Uani 1 1 d .
H17A H -0.038(2) 0.789(5) 0.0517(19) 0.097 Uiso 1 1 d R
H17B H -0.107(2) 0.670(4) 0.0771(18) 0.097 Uiso 1 1 d R
C18 C 0.22457(16) 0.9383(3) 0.32076(13) 0.0537(5) Uani 1 1 d .
H18A H 0.253262 0.906414 0.378450 0.080 Uiso 1 1 calc GR
H18B H 0.180481 1.048771 0.315043 0.080 Uiso 1 1 calc GR
H18C H 0.278195 0.968603 0.297878 0.080 Uiso 1 1 calc GR
H1B H 0.6465(17) 0.063(3) 0.4498(14) 0.057(6) Uiso 1 1 d .
H17C H -0.045(3) 0.579(6) 0.031(2) 0.141(15) Uiso 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 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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
C16 O4 C12 122.88(13)
C6 O3 H3 109.5
H1A N1 H1B 134.1
C2 N1 H1A 109.5
C2 N1 H1B 116.4(14)
C8 C7 C6 117.82(14)
C8 C7 C11 121.82(14)
C6 C7 C11 120.36(15)
C7 C8 H8 119.0
C7 C8 C9 122.00(14)
C9 C8 H8 119.0
O3 C6 C7 115.08(13)
O3 C6 C5 123.21(13)
C7 C6 C5 121.69(14)
O2 C4 C10 119.65(14)
O2 C4 C3 121.67(14)
C3 C4 C10 118.68(14)
C5 C10 C4 121.56(13)
C9 C10 C4 119.02(13)
C9 C10 C5 119.37(13)
C6 C5 C10 119.05(13)
C6 C5 C12 118.73(13)
C10 C5 C12 122.08(13)
O4 C12 C5 110.27(12)
C13 C12 O4 121.40(13)
C13 C12 C5 128.28(14)
C8 C9 C10 119.98(14)
C8 C9 C1 118.82(13)
C10 C9 C1 121.20(13)
N1 C2 C1 113.62(15)
N1 C2 C3 126.55(16)
C3 C2 C1 119.81(14)
O1 C1 C9 122.92(14)
O1 C1 C2 119.30(14)
C9 C1 C2 117.78(13)
O4 C16 C15 117.07(14)
O5 C16 O4 115.78(16)
O5 C16 C15 127.14(15)
C4 C3 H3A 118.4
C2 C3 C4 123.13(14)
C2 C3 H3A 118.4
C12 C13 C14 116.80(15)
C12 C13 C18 122.64(15)
C14 C13 C18 120.48(15)
C13 C14 H14 118.4
C15 C14 C13 123.15(16)
C15 C14 H14 118.4
C16 C15 C17 117.91(18)
C14 C15 C16 118.56(14)
C14 C15 C17 123.53(19)
C7 C11 H11A 109.5
C7 C11 H11B 109.5
C7 C11 H11C 109.5
H11A C11 H11B 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
C15 C17 H17A 108(2)
C15 C17 H17B 107.2(18)
C15 C17 H17C 115(2)
H17A C17 H17B 104(3)
H17A C17 H17C 116(3)
H17B C17 H17C 105(3)
C13 C18 H18A 109.5
C13 C18 H18B 109.5
C13 C18 H18C 109.5
H18A C18 H18B 109.5
H18A C18 H18C 109.5
H18B C18 H18C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O4 C12 1.3762(18)
O4 C16 1.3681(19)
O1 C1 1.2190(18)
O3 H3 0.8200
O3 C6 1.3525(19)
O2 C4 1.2325(19)
O5 C16 1.220(2)
N1 H1A 0.8200
N1 C2 1.337(2)
N1 H1B 0.91(2)
C7 C8 1.378(2)
C7 C6 1.404(2)
C7 C11 1.506(2)
C8 H8 0.9300
C8 C9 1.395(2)
C6 C5 1.404(2)
C4 C10 1.505(2)
C4 C3 1.429(2)
C10 C5 1.405(2)
C10 C9 1.400(2)
C5 C12 1.483(2)
C12 C13 1.344(2)
C9 C1 1.468(2)
C2 C1 1.507(2)
C2 C3 1.358(2)
C16 C15 1.442(3)
C3 H3A 0.9300
C13 C14 1.433(2)
C13 C18 1.500(2)
C14 H14 0.9300
C14 C15 1.346(3)
C15 C17 1.500(2)
C11 H11A 0.9600
C11 H11B 0.9600
C11 H11C 0.9600
C17 H17A 0.85(3)
C17 H17B 0.95(3)
C17 H17C 0.90(4)
C18 H18A 0.9600
C18 H18B 0.9600
C18 H18C 0.9600
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 145721043
