Prenylated Diresorcinols Inhibit Bacterial Quorum Sensing.
Paguigan, Noemi D.; Rivera-Chávez, José; Stempin, Justin J.; Augustinović, Mario; Noras, Aleksandra I.; Raja, Huzefa A.; Todd, Daniel A.; Triplett, Kathleen D.; Day, Cynthia; Figueroa, Mario; Hall, Pamela R.; Cech, Nadja B.; Oberlies, Nicholas H.; Journal of natural products 82 (2019) 550–558; doi:10.1021/acs.jnatprod.8b00925

data_1552712
_publ_section_title
;
 Prenylated Diresorcinols Inhibit Bacterial Quorum Sensing.
;
_journal_issue                   3
_journal_name_full               'Journal of natural products'
_journal_page_first              550
_journal_page_last               558
_journal_paper_doi               10.1021/acs.jnatprod.8b00925
_journal_volume                  82
_journal_year                    2019
_chemical_formula_sum            'C20 H20 O5'
_chemical_formula_weight         340.36
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                69.8100(10)
_cell_angle_beta                 77.6290(10)
_cell_angle_gamma                77.2120(10)
_cell_formula_units_Z            2
_cell_length_a                   7.3973(5)
_cell_length_b                   11.0738(8)
_cell_length_c                   12.0820(9)
_cell_measurement_reflns_used    4964
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      29.88
_cell_measurement_theta_min      3.56
_cell_volume                     895.52(11)
_computing_cell_refinement       'Bruker APEX2 v2014.11-0'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker APEX2 v2014.11-0'
_computing_molecular_graphics    'Bruker APEX2 v2014.11-0'
_computing_publication_material  'Bruker APEX2 v2014.11-0'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker APEX CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0233
_diffrn_reflns_av_unetI/netI     0.0466
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            17054
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_reduction_process narrow-frame
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.987
_diffrn_reflns_theta_min         3.556
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 Data were corrected for scaling  using the
 multi-scan technique (SADABS).  The
 calculated minimum and maximum transmission
 coefficients (based on crystal size) are 0.973 and 0.987.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.262
_exptl_crystal_description       irregular
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.140
_exptl_transmission_factor_max   0.7451
_exptl_transmission_factor_min   0.7400
_refine_diff_density_max         0.334
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.4(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     465
_refine_ls_number_reflns         9966
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0607
_refine_ls_R_factor_gt           0.0463
_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^)+(0.0675P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1151
_refine_ls_wR_factor_ref         0.1230
_reflns_Friedel_coverage         1.000
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.987
_reflns_number_gt                8084
_reflns_number_total             9966
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np8b00925_si_002.cif
_cod_data_source_block           a22x_0m_a
_cod_database_code               1552712
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.973
_shelx_estimated_absorpt_t_max   0.987
_computing.bruker_data_scaling   'SADABS V2014/5 (Bruker AXS)'
_shelx_res_checksum              1385
_shelx_hkl_checksum              16480