Antibacterial Salinaphthoquinones from a Strain of the Bacterium <i>Salinispora arenicola</i> Recovered from the Marine Sediments of St. Peter and St. Paul Archipelago, Brazil.
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.; Journal of natural products 82 (2019) 1831–1838; doi:10.1021/acs.jnatprod.9b00062

data_1552680
_publ_section_title
;
 Antibacterial Salinaphthoquinones from a Strain of the Bacterium
 <i>Salinispora arenicola</i> 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_absolute_configuration ad
_chemical_formula_moiety         'C24 H27 N O7, H2 O'
_chemical_formula_sum            'C24 H29 N O8'
_chemical_formula_weight         459.48
_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
_audit_creation_date             2019-04-30
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.18 svn.r3508 for OlexSys, GUI svn.r5497)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.6893(3)
_cell_length_b                   15.2942(6)
_cell_length_c                   16.9431(6)
_cell_measurement_reflns_used    9139
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      66.91
_cell_measurement_theta_min      3.89
_cell_volume                     2251.67(14)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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      150.01
_diffrn_detector_type            'Bruker PHOTON II'
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1241
_diffrn_reflns_av_unetI/netI     0.0679
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            42312
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.226
_diffrn_reflns_theta_min         3.894
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.849
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.4638
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1225 before and 0.0757 after correction. The Ratio of minimum to maximum transmission is 0.6159. The \l/2 correction factor is Not present.'
_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    1.355
_exptl_crystal_description       prism
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.148
_exptl_crystal_size_mid          0.111
_exptl_crystal_size_min          0.058
_refine_diff_density_max         0.189
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details
;
 Flack x determined using 669 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.3(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         4073
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.1298
_refine_ls_R_factor_gt           0.0715
_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^)+(0.1252P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1876
_refine_ls_wR_factor_ref         0.2318
_reflns_Friedel_coverage         0.736
_reflns_Friedel_fraction_full    0.977
_reflns_Friedel_fraction_max     0.975
_reflns_number_gt                2179
_reflns_number_total             4073
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np9b00062_si_004.cif
_cod_data_source_block           bra213a6decp2
_cod_database_code               1552680
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.952
_shelx_estimated_absorpt_t_min   0.885
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H3(0.118) H1WA(0.134) H1WB(0.134) H1A(0.105) H1B(0.105)
 H14(0.088) H8(0.088) H3A(0.091) H17(0.095) H13(0.085) H15(0.091) H19(0.094)
 H18(0.087) H16(0.094) H11A(0.122) H11B(0.122) H11C(0.122) H21A(0.117)
 H21B(0.117) H21C(0.117) H23A(0.132) H23B(0.132) H23C(0.132) H22A(0.137)
 H22B(0.137) H22C(0.137) H24A(0.134) H24B(0.134) H24C(0.134)
 Fixed X: H3(0.541831) H1WA(0.616301) H1WB(0.612356) H1A(0.53217)
 H1B(0.598448) H14(0.203966) H8(0.673877) H3A(0.446531) H17(-0.033201)
 H13(0.203009) H15(-0.031693) H19(0.313102) H18(0.227195) H16(-0.175834)
 H11A(0.572286) H11B(0.704016) H11C(0.738156) H21A(0.26498) H21B(0.089842)
 H21C(0.202722) H23A(0.012655) H23B(-0.152723) H23C(-0.013542) H22A(-0.052868)
 H22B(-0.187277) H22C(-0.033078) H24A(0.143721) H24B(0.26581) H24C(0.32207)
 Fixed Y: H3(0.580792) H1WA(0.716454) H1WB(0.737004) H1A(0.000828)
 H1B(0.037049) H14(0.502377) H8(0.342248) H3A(0.102223) H17(0.721446)
 H13(0.36732) H15(0.49457) H19(0.647512) H18(0.705793) H16(0.590716)
 H11A(0.555113) H11B(0.493602) H11C(0.551625) H21A(0.368171) H21B(0.388107)
 H21C(0.466648) H23A(0.614527) H23B(0.653615) H23C(0.718093) H22A(0.430031)
 H22B(0.425243) H22C(0.369592) H24A(0.807987) H24B(0.785803) H24C(0.797329)
 Fixed Z: H3(0.598213) H1WA(0.641126) H1WB(0.559376) H1A(0.594977)
 H1B(0.518371) H14(0.649457) H8(0.464602) H3A(0.697367) H17(0.707713)
 H13(0.71614) H15(0.76782) H19(0.619532) H18(0.750282) H16(0.691114)
 H11A(0.467606) H11B(0.431908) H11C(0.508535) H21A(0.858003) H21B(0.834982)
 H21C(0.858301) H23A(0.844167) H23B(0.822191) H23C(0.843139) H22A(0.61018)
 H22B(0.674609) H22C(0.686612) H24A(0.629669) H24B(0.561845) H24C(0.65118)
;
_shelx_res_checksum              20037
_shelx_hkl_checksum              76313
_olex2_submission_special_instructions 'No special instructions were received'