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_7155695
_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         'C2 H6 O S, 0.25(C26 H22 N10 O6)'
_chemical_formula_sum            'C8.5 H11.5 N2.5 O2.5 S'
_chemical_formula_weight         220.76
_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   geom
_audit_creation_date             2017-03-22
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_audit_update_record
;
2017-04-03 deposited with the CCDC.
2017-06-16 downloaded from the CCDC.
;
_cell_angle_alpha                92.357(2)
_cell_angle_beta                 104.697(3)
_cell_angle_gamma                106.384(2)
_cell_formula_units_Z            4
_cell_length_a                   9.7434(5)
_cell_length_b                   9.8225(5)
_cell_length_c                   12.0241(6)
_cell_measurement_reflns_used    4294
_cell_measurement_temperature    153.54
_cell_measurement_theta_max      25.857
_cell_measurement_theta_min      2.965
_cell_volume                     1060.01(10)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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      153.54
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_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  0.0430
_diffrn_reflns_av_unetI/netI     0.0419
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            14261
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         3.236
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.289
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6748
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1351 before and 0.0522 after correction. The Ratio of minimum to maximum transmission is 0.9050. The \l/2 correction factor is 0.00150.'
_exptl_crystal_colour            'light yellow'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_description       plate
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.101
_exptl_crystal_size_mid          0.063
_exptl_crystal_size_min          0.057
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.348
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     268
_refine_ls_number_reflns         3686
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0556
_refine_ls_R_factor_gt           0.0394
_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^)+(0.0406P)^2^+0.6227P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0933
_refine_ls_wR_factor_ref         0.1032
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2869
_reflns_number_total             3686
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ob01011g2.cif
_cod_data_source_block           shashidhar_17sep15_0m_a
_cod_original_cell_volume        1060.01(9)
_cod_original_formula_sum        'C8.50 H11.50 N2.50 O2.50 S'
_cod_database_code               7155695
_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
 At 1.5 times of:
  All C(H,H,H) groups, All C(H,H,H,H,H,H) groups
2. Others
 Fixed Sof: S1B(0.85) H1BA(0.85) H1BB(0.85) H1BC(0.85) H1BD(0.15) H1BE(0.15)
 H1BF(0.15) H2BA(0.85) H2BB(0.85) H2BC(0.85) H2BD(0.15) H2BE(0.15) H2BF(0.15)
 S1(0.15)
3.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C12(H12A,H12B)
3.b Me refined with riding coordinates:
 C1B(H1BA,H1BB,H1BC), C1B(H1BD,H1BE,H1BF), C2B(H2BA,H2BB,H2BC), C2B(H2BD,H2BE,
 H2BF)
3.c Aromatic/amide H refined with riding coordinates:
 N4(H4), N5(H5), C1(H1), C7(H7), C8(H8), C9(H9), C10(H10)
3.d Idealised Me refined as rotating group:
 C1A(H1AA,H1AB,H1AC), C2A(H2AA,H2AB,H2AC)
;
_olex2_submission_special_instructions 'No special instructions were received'