Design, synthesis and biological evaluation of 1,2,3-triazole based 2-aminobenzimidazoles as novel inhibitors of LasR dependent quorum sensing in Pseudomonas aeruginosa
Srinivasarao, Singireddi; Nandikolla, Adinarayana; Nizalapur, Shashidhar; Yu, Tsz Tin; Pulya, Sravani; Ghosh, Balaram; Murugesan, Sankaranarayanan; Kumar, Naresh; Chandra Sekhar, Kondapalli Venkata Gowri; RSC Advances 9 (2019) 29273–; doi:10.1039/C9RA05059K

data_7233924
_publ_section_title
;
 Design, synthesis and biological evaluation of 1,2,3-triazole based
 2-aminobenzimidazoles as novel inhibitors of LasR dependent quorum
 sensing in Pseudomonas aeruginosa
;
_journal_issue                   50
_journal_name_full               'RSC Advances'
_journal_page_first              29273
_journal_paper_doi               10.1039/C9RA05059K
_journal_volume                  9
_journal_year                    2019
_chemical_formula_moiety         'C20 H28 N6 O'
_chemical_formula_sum            'C20 H28 N6 O'
_chemical_formula_weight         368.48
_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
_atom_sites_solution_primary     direct
_audit_creation_date             2019-03-16
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-04-26 deposited with the CCDC.    2019-09-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.614(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.8646(7)
_cell_length_b                   5.4019(2)
_cell_length_c                   20.0357(6)
_cell_measurement_reflns_used    3122
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      76.7190
_cell_measurement_theta_min      5.0320
_cell_volume                     2041.61(12)
_computing_cell_refinement       'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w     55.00  89.00   0.50   10.00    --    0.00  77.00-150.00   68
  2  \w     39.00  87.00   0.50   10.00    --    0.00  77.00 -30.00   96
  3  \w    -13.00  88.00   0.50   10.00    --    0.00  77.00-180.00  202
  4  \w     20.00  47.00   0.50   10.00    --    0.00  77.00-150.00   54
  5  \w    -15.00  10.00   0.50   10.00    --    0.00  77.00 -30.00   50
  6  \w     70.00 122.00   0.50   40.00    --  107.20 -30.00  30.00  104
  7  \w     53.00  96.00   0.50   40.00    --  107.20 -82.00-150.00   86
  8  \w     82.00 137.00   0.50   40.00    --  107.20 -82.00  90.00  110
  9  \w     25.00  69.00   0.50   40.00    --  107.20 -30.00-180.00   88
 10  \w     18.00 123.00   0.50   40.00    --  107.20 -15.00-150.00  210
 11  \w     23.00 120.00   0.50   40.00    --  107.20 -30.00 -60.00  194
 12  \w     27.00  52.00   0.50   40.00    --  107.20 -30.00  30.00   50
 13  \w     22.00 138.00   0.50   40.00    --  107.20 -77.00 -90.00  232
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro: Kappa dual home/near'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0003493000
_diffrn_orient_matrix_UB_12      0.0386622000
_diffrn_orient_matrix_UB_13      0.0761754000
_diffrn_orient_matrix_UB_21      -0.0815681000
_diffrn_orient_matrix_UB_22      0.0152679000
_diffrn_orient_matrix_UB_23      -0.0010974000
_diffrn_orient_matrix_UB_31      -0.0044362000
_diffrn_orient_matrix_UB_32      -0.2821245000
_diffrn_orient_matrix_UB_33      0.0103412000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0482
_diffrn_reflns_av_unetI/netI     0.0635
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       3
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            10329
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.897
_diffrn_reflns_theta_min         4.414
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.619
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.43307
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.20a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.199
_exptl_crystal_description       needle
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.421
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         4308
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0834
_refine_ls_R_factor_gt           0.0671
_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^)+(0.1196P)^2^+0.1169P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1867
_refine_ls_wR_factor_ref         0.2036
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3157
_reflns_number_total             4308
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ra05059k2.cif
_cod_data_source_block           exp_399-ab-4r
_cod_database_code               7233924
_shelx_shelxl_version_number     2016/4
_reflns_odcompleteness_completeness 99.80
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_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
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C13(H13A,H13B), C12(H12A,H12B), C18(H18A,H18B), C15(H15A,H15B),
 C16(H16A,H16B), C14(H14A,H14B), C17(H17A,H17B), C19(H19A,H19B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), N3(H3), C5(H5), C10(H10), C3(H3A), C2(H2), C4(H4)
2.c Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C)
;
_shelx_res_checksum              94952
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.063
_oxdiff_exptl_absorpt_empirical_full_min 0.378