Hybrids of acylated homoserine lactone and nitric oxide donors as inhibitors of quorum sensing and virulence factors in Pseudomonas aeruginosa.
Kutty, Samuel K.; Barraud, Nicolas; Ho, Kitty K. K.; Iskander, George M.; Griffith, Renate; Rice, Scott A.; Bhadbhade, Mohan; Willcox, Mark D. P.; Black, David StC; Kumar, Naresh; Organic & biomolecular chemistry 13 (2015) 9850–9861; doi:10.1039/c5ob01373a

data_7154637
_publ_section_title
;
 Hybrids of acylated homoserine lactone and nitric oxide donors as
 inhibitors of quorum sensing and virulence factors in Pseudomonas
 aeruginosa.
;
_journal_issue                   38
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              9850
_journal_page_last               9861
_journal_paper_doi               10.1039/c5ob01373a
_journal_volume                  13
_journal_year                    2015
_chemical_formula_moiety         'C18 H17 N7 O10, C H Cl3'
_chemical_formula_sum            'C19 H18 Cl3 N7 O10'
_chemical_formula_weight         610.75
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2015-06-24
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2015-06-24 deposited with the CCDC.
2015-08-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 108.884(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.6131(5)
_cell_length_b                   26.0490(10)
_cell_length_c                   8.1912(4)
_cell_measurement_reflns_used    4890
_cell_measurement_temperature    156(2)
_cell_measurement_theta_max      23.892
_cell_measurement_theta_min      3.058
_cell_volume                     2546.43(19)
_computing_cell_refinement       'SAINT v7.46A (Bruker, 2008)'
_computing_data_reduction        'SAINT v7.46A (Bruker, 2008)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_diffrn_ambient_temperature      155.86
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0378
_diffrn_reflns_av_unetI/netI     0.0354
_diffrn_reflns_laue_measured_fraction_full 0.996
_diffrn_reflns_laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            17884
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         1.563
_exptl_absorpt_coefficient_mu    0.428
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_correction_T_min  0.6667
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2007/4 (Bruker,2007/4) was used for absorption correction.
wR2(int) was 0.0516 before and 0.0439 after correction.
The Ratio of minimum to maximum transmission is 0.8938.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.593
_exptl_crystal_description       plate
_exptl_crystal_F_000             1248
_exptl_crystal_size_max          0.297
_exptl_crystal_size_mid          0.102
_exptl_crystal_size_min          0.047
_refine_diff_density_max         1.442
_refine_diff_density_min         -1.246
_refine_diff_density_rms         0.292
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   3.511
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     380
_refine_ls_number_reflns         4460
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      3.507
_refine_ls_R_factor_all          0.2858
_refine_ls_R_factor_gt           0.2697
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.6670
_refine_ls_wR_factor_ref         0.6748
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3699
_reflns_number_total             4460
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ob01373a2.cif
_cod_data_source_block           sam12_p21byc
_cod_depositor_comments
'Adding full bibliography for 7154637--7154638.cif.'
_cod_database_code               7154637
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H) groups
2. Shared sites
{C2X, C2X'}
{C19, C19'}
3. Uiso/Uaniso restraints and constraints
Uanis(C2X) = Uanis(C2X')
Uanis(C19) = Uanis(C19')
4. Rigid body (RIGU) restrains
 O10, C3X
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 O0AA, C1AA
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C19, C18
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 N7, C0AA
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Fixed Sof: C19(0.5) C18(0.5) O10(0.5) C3X(0.5) H3XA(0.5) H3XB(0.5) C2X(0.5)
 H2XA(0.5) H2XB(0.5) C0AA(0.5) O0AA(0.5) C1AA(0.5) H1AA(0.5) H1AB(0.5)
 C19'(0.5) C2X'(0.5)
6.a Ternary CH refined with riding coordinates:
 C1CL(H1CL)
6.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C9(H9A,H9B), C12(H12A,H12B), C10(H10A,H10B), C3X(H3XA,H3XB),
 C2X(H2XA,H2XB), C1AA(H1AA,H1AB)
6.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C1(H1), C15(H15), C14(H14)
6.d Idealised tetrahedral OH refined as rotating group:
 O6(H6A)
;
_shelx_res_checksum              76997
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'