Conformational study of (Z)-5-(4-chlorobenzylidene)-2-[4-(2-hydroxyethyl)piperazin-1-yl]-3H-imidazol-4(5H)-one in different environments: insight into the structural properties of bacterial efflux pump inhibitors.
Żesławska, Ewa; Nitek, Wojciech; Handzlik, Jadwiga; Acta crystallographica. Section C, Structural chemistry 73 (2017) 1151–1157; doi:10.1107/S2053229617016461

data_2311969
_publ_section_title
;
 Conformational study of
 (Z)-5-(4-chlorobenzylidene)-2-[4-(2-hydroxyethyl)piperazin-1-yl]-3H-imidazol-4(5H)-one
 in different environments: insight into the structural properties of
 bacterial efflux pump inhibitors.
;
_journal_coeditor_code           KY3131
_journal_issue                   'Pt 12'
_journal_name_full
'Acta crystallographica. Section C, Structural chemistry'
_journal_page_first              1151
_journal_page_last               1157
_journal_paper_doi               10.1107/S2053229617016461
_journal_volume                  73
_journal_year                    2017
_chemical_formula_iupac          'C16 H20 Cl N4 O2 +, C6 H4 N O2 -'
_chemical_formula_moiety         'C16 H20 Cl N4 O2 +, C6 H4 N O2 -'
_chemical_formula_sum            'C22 H24 Cl N5 O4'
_chemical_formula_weight         457.91
_chemical_name_systematic
;4-[(<i>Z</i>)-4-(4-Chlorobenzylidene)-5-oxo-3,4-dihydro-1<i>H</i>-imidazol-2-yl]-1-(2-hydroxyethyl)piperazin-1-ium
pyridine-2-carboxylate
;
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 103.499(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   22.6220(4)
_cell_length_b                   7.1937(2)
_cell_length_c                   13.5315(7)
_cell_measurement_reflns_used    7626
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      0.998
_cell_volume                     2141.23(13)
_computing_cell_refinement
;
SCALEPACK (Otwinowski & Minor, 1997)
;
_computing_data_collection
;
COLLECT (Bruker, 2004)
;
_computing_data_reduction
;
DENZO and SCALEPACK (Otwinowski & Minor, 1997)
;
_computing_molecular_graphics
;
ORTEP-3 (Farrugia, 2012) and Mercury (Macrae <i>et al.</i>,
2008)
;
_computing_publication_material
;
publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL97 (Sheldrick, 2008) and SHELXL2014 (Sheldrick, 2015)
;
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device       '95mm CCD camera on \k-goniostat'
_diffrn_measurement_device_type  'Bruker KappaCCD'
_diffrn_measurement_method       CCD
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0453
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            14522
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.221
_diffrn_reflns_theta_min         2.979
_exptl_absorpt_coefficient_mu    0.219
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.9012
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(DENZO-SMN; Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.42
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.597
_refine_diff_density_min         -0.6
_refine_ls_extinction_coef       0.0045(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method
;
SHELXL2014 (Sheldrick, 2015)
;
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     302
_refine_ls_number_reflns         4720
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.064
_refine_ls_R_factor_gt           0.0434
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0360P)^2^+1.8941P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0935
_refine_ls_wR_factor_ref         0.1027
_reflns_number_gt                3651
_reflns_number_total             4720
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ky3131sup1.cif
_cod_data_source_block           3a
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2311969
_shelx_hkl_checksum              82496
_shelx_res_checksum              40651
_shelxl_version_number           .2013