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_2311970
_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 +, C8 H6 N O4 -'
_chemical_formula_moiety         'C16 H20 Cl N4 O2 +, C8 H6 N O4 -'
_chemical_formula_sum            'C24 H26 Cl N5 O6'
_chemical_formula_weight         515.95
_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
2-(4-nitrophenyl)acetate
;
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                66.859(6)
_cell_angle_beta                 85.085(4)
_cell_angle_gamma                81.332(5)
_cell_formula_units_Z            2
_cell_length_a                   7.8667(4)
_cell_length_b                   11.9015(7)
_cell_length_c                   14.4406(9)
_cell_measurement_reflns_used    4966
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      71.8205
_cell_measurement_theta_min      3.3297
_cell_volume                     1228.51(13)
_computing_cell_refinement
;
CrysAlis PRO (Rigaku OD, 2015)
;
_computing_data_collection
;
CrysAlis PRO (Rigaku OD, 2015)
;
_computing_data_reduction
;
CrysAlis PRO (Rigaku OD, 2015)
;
_computing_molecular_graphics
;
ORTEP-3 (Farrugia, 2012) and Mercury (Macrae <i>et al.</i>,
2008)
;
_computing_publication_material
;
publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2013 (Sheldrick, 2015)
;
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean 10.3756
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'Rigaku SuperNova Dual Source diffractometer with an Atlas detector'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0721
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            17827
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.821
_diffrn_reflns_theta_min         3.33
_exptl_absorpt_coefficient_mu    1.808
_exptl_absorpt_correction_T_max  0.947
_exptl_absorpt_correction_T_min  0.824
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
(CrysAlis PRO; Rigaku OD, 2015)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             540
_exptl_crystal_size_max          0.485
_exptl_crystal_size_mid          0.169
_exptl_crystal_size_min          0.135
_refine_diff_density_max         0.244
_refine_diff_density_min         -0.404
_refine_ls_extinction_coef       0.0034(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method
;
SHELXL2013 (Sheldrick, 2015)
;
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     354
_refine_ls_number_reflns         4750
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0906
_refine_ls_R_factor_gt           0.0675
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1334P)^2^+0.0797P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1888
_refine_ls_wR_factor_ref         0.2227
_reflns_number_gt                3217
_reflns_number_total             4750
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ky3131sup1.cif
_cod_data_source_block           3b
_cod_database_code               2311970
_shelx_hkl_checksum              70249
_shelx_res_checksum              41050
_shelxl_version_number           .2013