Synthesis and Biological Evaluation of Novel Acyclic and Cyclic Glyoxamides as Bacterial Quorum Sensing and Biofilm Inhibitors
Nizalapur, Shashidhar; Kimyon, Onder; Yee, Eugene; Bhadbhade, Mohan; Manefield, Mike; Willcox, Mark D.P.; Black, David StClair; Kumar, Naresh; Org. Biomol. Chem.  (2017) –; doi:10.1039/C7OB01011G

data_7155694
_publ_section_title
;
 Synthesis and Biological Evaluation of Novel Acyclic and Cyclic
 Glyoxamides as Bacterial Quorum Sensing and Biofilm Inhibitors
;
_journal_name_full               'Org. Biomol. Chem.'
_journal_paper_doi               10.1039/C7OB01011G
_journal_year                    2017
_chemical_formula_moiety         'C26 H22 N10 O6, 2(H2 O)'
_chemical_formula_sum            'C26 H26 N10 O8'
_chemical_formula_weight         606.57
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2017-03-31
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_audit_update_record
;
2017-04-03 deposited with the CCDC.
2017-06-16 downloaded from the CCDC.
;
_cell_angle_alpha                60.81(2)
_cell_angle_beta                 86.52(3)
_cell_angle_gamma                88.14(3)
_cell_formula_units_Z            1
_cell_length_a                   7.428(4)
_cell_length_b                   10.364(7)
_cell_length_c                   10.401(6)
_cell_measurement_reflns_used    776
_cell_measurement_temperature    157.54
_cell_measurement_theta_max      18.828
_cell_measurement_theta_min      2.251
_cell_volume                     697.7(7)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_temperature      157.54
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1031
_diffrn_reflns_av_unetI/netI     0.1651
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6795
_diffrn_reflns_point_group_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        24.995
_diffrn_reflns_theta_max         24.995
_diffrn_reflns_theta_min         2.246
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.5348
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1810 before and 0.0610 after correction. The Ratio of minimum to maximum transmission is 0.7174. The \l/2 correction factor is 0.00150.'
_exptl_crystal_colour            'light white'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.443
_exptl_crystal_description       plate
_exptl_crystal_F_000             316
_exptl_crystal_size_max          0.106
_exptl_crystal_size_mid          0.086
_exptl_crystal_size_min          0.048
_refine_diff_density_max         0.302
_refine_diff_density_min         -0.298
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.918
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     207
_refine_ls_number_reflns         2401
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.918
_refine_ls_R_factor_all          0.1642
_refine_ls_R_factor_gt           0.0659
_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^)+(0.0661P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1290
_refine_ls_wR_factor_ref         0.1668
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1069
_reflns_number_total             2401
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ob01011g2.cif
_cod_data_source_block           shashidhar_cu_p1bar_reprocess_a
_cod_original_cell_volume        697.8(7)
_cod_database_code               7155694
_shelx_shelxl_version_number     2014/7
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C12(H12A,H12B)
2.b Aromatic/amide H refined with riding coordinates:
 N4(H4), N006(H006), C1(H1), C8(H8), C9(H9), C10(H10), C11(H11)
;
_olex2_submission_special_instructions 'No special instructions were received'