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The 2-amine derivatives of 5-aryl­idene-3H-imidazol-4(5H)-one are a new class of bacterial efflux pump inhibitors, the chemical compounds that are able to restore anti­biotic efficacy against multidrug resistant bacteria. 5-Aryl­idene-3H-imidazol-4(5H)-ones with a piperazine ring at position 2 reverse the mechanisms of multidrug resistance (MDR) of the particularly dangerous Gram-negative bacteria E. coli by inhibition of the efflux pump AcrA/AcrB/TolC (a main multidrug resistance mechanism in Gram-negative bacteria, consisting of a membrane fusion protein, AcrA, a Resistant-Nodulation-Division protein, AcrB, and an outer membrane factor, TolC). In order to study the influence of the environment on the conformation of (Z)-5-(4-chloro­benzyl­idene)-2-[4-(2-hy­droxy­eth­yl)piperazin-1-yl]-3H-imidazol-4(5H)-one, (3), two different salts were prepared, namely with picolinic acid {systematic name: 4-[(Z)-4-(4-chloro­benzyl­idene)-5-oxo-3,4-di­hydro-1H-imidazol-2-yl]-1-(2-hy­droxy­eth­yl)piperazin-1-ium pyridine-2-carboxyl­ate, C16H20ClN4O2+·C6H4NO2, (3a)} and 4-nitro­phenyl­acetic acid {systematic name: 4-[(Z)-4-(4-chloro­benzyl­idene)-5-oxo-3,4-di­hydro-1H-imidazol-2-yl]-1-(2-hy­droxy­eth­yl)piperazin-1-ium 2-(4-nitro­phen­yl)acetate, C16H20ClN4O2+·C8H6NO4, (3b)}. The crystal structures of the new salts were determined by X-ray diffraction. In both crystal structures, the mol­ecule of (3) is protonated at an N atom of the piperazine ring by proton transfer from the corresponding acid. The carboxyl­ate group of picolinate engages in hydrogen bonds with three mol­ecules of the cation of (3), whereas the carboxyl­ate group of 4-nitro­phenyl­acetate engages in hydrogen bonds with only two mol­ecules of (3). As a consequence of these inter­actions, different orientations of the hy­droxy­ethyl group of (3) are observed. The crystal structures are additionally stabilized by both C—H...N [in (3a)] and C—H...O [in (3a) and (3b)] inter­molecular inter­actions. The geometry of the imidazolone fragment was compared with other crystal structures possessing this moiety. The tautomer observed in the crystal structures presented here, namely 3H-imidazol-4(5H)-one [systematic name: 1H-imidazol-5(4H)-one], is also that most frequently observed in other structures containing this heterocycle.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229617016461/ky3131sup1.cif
Contains datablocks 3a, 3b, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229617016461/ky31313asup2.hkl
Contains datablock 3a

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229617016461/ky31313asup4.cml
Supplementary material

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229617016461/ky31313bsup3.hkl
Contains datablock 3b

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229617016461/ky31313bsup5.cml
Supplementary material

CCDC references: 1585810; 1585809

Computing details top

Data collection: COLLECT (Bruker, 2004) for (3a); CrysAlis PRO (Rigaku OD, 2015) for (3b). Cell refinement: SCALEPACK (Otwinowski & Minor, 1997) for (3a); CrysAlis PRO (Rigaku OD, 2015) for (3b). Data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997) for (3a); CrysAlis PRO (Rigaku OD, 2015) for (3b). Program(s) used to refine structure: SHELXL97 (Sheldrick, 2008) and SHELXL2014 (Sheldrick, 2015) for (3a); SHELXL2013 (Sheldrick, 2015) for (3b). For both structures, molecular graphics: ORTEP-3 (Farrugia, 2012) and Mercury (Macrae et al., 2008); software used to prepare material for publication: publCIF (Westrip, 2010).

4-[(Z)-4-(4-Chlorobenzylidene)-5-oxo-3,4-dihydro-1H-imidazol-2-yl]-1-(2-hydroxyethyl)piperazin-1-ium pyridine-2-carboxylate (3a) top
Crystal data top
C16H20ClN4O2+·C6H4NO2F(000) = 960
Mr = 457.91Dx = 1.42 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 7626 reflections
a = 22.6220 (4) Åθ = 1.0–27.5°
b = 7.1937 (2) ŵ = 0.22 mm1
c = 13.5315 (7) ÅT = 120 K
β = 103.499 (2)°Plate, colourless
V = 2141.23 (13) Å30.39 × 0.35 × 0.11 mm
Z = 4
Data collection top
Bruker KappaCCD
diffractometer
4720 independent reflections
Horizonally mounted graphite crystal monochromator3651 reflections with I > 2σ(I)
Detector resolution: 9 pixels mm-1Rint = 0.045
CCD scansθmax = 27.2°, θmin = 3.0°
Absorption correction: multi-scan
(DENZO-SMN; Otwinowski & Minor, 1997)
h = 2829
Tmin = 0.901, Tmax = 1.000k = 99
14522 measured reflectionsl = 1717
Refinement top
Refinement on F2Hydrogen site location: mixed
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.043 w = 1/[σ2(Fo2) + (0.036P)2 + 1.8941P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.103(Δ/σ)max < 0.001
S = 1.02Δρmax = 0.60 e Å3
4720 reflectionsΔρmin = 0.6 e Å3
302 parametersExtinction correction: SHELXL2014 (Sheldrick, 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraintsExtinction coefficient: 0.0045 (9)
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C120.40993 (9)0.1213 (3)0.08873 (15)0.0256 (4)
H120.4040.24150.11840.031*
C110.43467 (9)0.0182 (3)0.13694 (16)0.0305 (5)
H110.44520.00550.19970.037*
C100.44382 (8)0.1919 (3)0.09286 (16)0.0272 (5)
C90.42888 (8)0.2292 (3)0.00131 (16)0.0256 (4)
H90.43590.34920.02850.031*
C80.40350 (8)0.0900 (3)0.04651 (15)0.0222 (4)
H80.39280.11520.10910.027*
C70.39348 (8)0.0877 (3)0.00314 (14)0.0201 (4)
C60.36503 (8)0.2375 (3)0.04789 (14)0.0189 (4)
H60.36720.35710.01920.023*
C50.33611 (8)0.2303 (2)0.12419 (13)0.0162 (4)
N10.32477 (7)0.0767 (2)0.18039 (11)0.0166 (3)
C20.28577 (8)0.1363 (2)0.23098 (13)0.0140 (3)
N30.27035 (7)0.3234 (2)0.21673 (11)0.0149 (3)
C40.30176 (8)0.3934 (2)0.14909 (13)0.0157 (4)
O40.29908 (6)0.55285 (17)0.11713 (9)0.0198 (3)
N20.26329 (6)0.03067 (19)0.29710 (11)0.0145 (3)
C130.27837 (8)0.1682 (2)0.29849 (13)0.0158 (4)
H13A0.32160.18340.29670.019*
H13B0.25310.22940.23750.019*
C140.26716 (8)0.2596 (2)0.39329 (13)0.0156 (4)
H14A0.27590.39430.39190.019*
H14B0.29480.20550.45410.019*
N40.20229 (7)0.2312 (2)0.39956 (11)0.0134 (3)
C160.19018 (8)0.0265 (2)0.40117 (13)0.0151 (4)
H16A0.21720.02980.4620.018*
H16B0.14760.00550.40540.018*
C150.20093 (8)0.0653 (2)0.30678 (13)0.0148 (4)
H15A0.17170.01580.24630.018*
H15B0.19410.20080.31010.018*
C170.18754 (8)0.3210 (2)0.49056 (13)0.0167 (4)
H17A0.14750.27480.49780.02*
H17B0.21830.28250.55190.02*
C180.18561 (8)0.5321 (2)0.48602 (13)0.0166 (4)
H18A0.15770.57580.42260.02*
H18B0.22660.58430.48990.02*
O10.16389 (6)0.58317 (19)0.57220 (9)0.0218 (3)
C200.03275 (8)0.3026 (2)0.06731 (14)0.0179 (4)
H200.03430.37080.00780.021*
C210.01453 (9)0.1790 (3)0.06659 (15)0.0238 (4)
H210.04640.16340.00750.029*
C220.01401 (9)0.0794 (3)0.15396 (16)0.0273 (5)
H220.04570.0060.15640.033*
C230.03350 (9)0.1064 (3)0.23782 (15)0.0248 (4)
H230.03390.03480.2970.03*
N50.07913 (7)0.2275 (2)0.24095 (11)0.0178 (3)
C190.07778 (8)0.3255 (2)0.15591 (13)0.0137 (3)
C240.12818 (8)0.4683 (2)0.16024 (13)0.0139 (4)
O30.16842 (5)0.47981 (17)0.24246 (9)0.0161 (3)
O20.12535 (6)0.56308 (17)0.08229 (9)0.0188 (3)
Cl10.47425 (3)0.36900 (9)0.15369 (4)0.04095 (18)
H30.2369 (11)0.386 (3)0.2308 (17)0.035 (6)*
H40.1785 (10)0.281 (3)0.3439 (16)0.020 (5)*
H10.1558 (12)0.709 (4)0.5709 (19)0.049 (8)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C120.0216 (10)0.0325 (11)0.0258 (10)0.0036 (8)0.0118 (8)0.0002 (9)
C110.0218 (10)0.0474 (14)0.0262 (11)0.0049 (9)0.0133 (8)0.0066 (10)
C100.0148 (9)0.0370 (12)0.0313 (11)0.0005 (8)0.0081 (8)0.0134 (9)
C90.0175 (9)0.0263 (10)0.0330 (11)0.0016 (8)0.0061 (8)0.0044 (9)
C80.0178 (9)0.0258 (10)0.0240 (10)0.0002 (8)0.0067 (8)0.0014 (8)
C70.0131 (8)0.0274 (10)0.0216 (9)0.0035 (7)0.0074 (7)0.0026 (8)
C60.0167 (9)0.0180 (9)0.0230 (10)0.0021 (7)0.0066 (7)0.0023 (7)
C50.0158 (8)0.0142 (8)0.0189 (9)0.0000 (7)0.0045 (7)0.0010 (7)
N10.0168 (7)0.0158 (7)0.0185 (8)0.0003 (6)0.0070 (6)0.0021 (6)
C20.0143 (8)0.0134 (8)0.0143 (8)0.0000 (7)0.0036 (6)0.0003 (7)
N30.0164 (7)0.0126 (7)0.0171 (7)0.0018 (6)0.0067 (6)0.0014 (6)
C40.0162 (8)0.0171 (9)0.0134 (8)0.0008 (7)0.0025 (7)0.0010 (7)
O40.0271 (7)0.0140 (6)0.0200 (7)0.0005 (5)0.0087 (5)0.0041 (5)
N20.0176 (7)0.0111 (7)0.0168 (7)0.0022 (6)0.0081 (6)0.0024 (6)
C130.0211 (9)0.0102 (8)0.0183 (9)0.0027 (7)0.0093 (7)0.0009 (7)
C140.0171 (9)0.0137 (8)0.0169 (9)0.0019 (7)0.0056 (7)0.0016 (7)
N40.0196 (8)0.0115 (7)0.0100 (7)0.0005 (6)0.0057 (6)0.0006 (6)
C160.0210 (9)0.0110 (8)0.0148 (8)0.0015 (7)0.0074 (7)0.0005 (7)
C150.0184 (9)0.0121 (8)0.0160 (8)0.0021 (7)0.0081 (7)0.0024 (7)
C170.0258 (9)0.0151 (9)0.0114 (8)0.0015 (7)0.0087 (7)0.0015 (7)
C180.0216 (9)0.0149 (9)0.0146 (8)0.0005 (7)0.0069 (7)0.0025 (7)
O10.0350 (8)0.0174 (7)0.0158 (6)0.0062 (6)0.0114 (6)0.0015 (5)
C200.0195 (9)0.0157 (9)0.0187 (9)0.0035 (7)0.0049 (7)0.0023 (7)
C210.0184 (9)0.0192 (10)0.0307 (11)0.0005 (8)0.0003 (8)0.0022 (8)
C220.0228 (10)0.0210 (10)0.0383 (12)0.0067 (8)0.0076 (9)0.0042 (9)
C230.0258 (10)0.0214 (10)0.0286 (11)0.0053 (8)0.0093 (8)0.0080 (8)
N50.0213 (8)0.0153 (7)0.0182 (8)0.0010 (6)0.0074 (6)0.0038 (6)
C190.0173 (8)0.0108 (8)0.0148 (8)0.0017 (7)0.0074 (7)0.0003 (6)
C240.0170 (8)0.0109 (8)0.0157 (9)0.0027 (6)0.0078 (7)0.0011 (7)
O30.0186 (6)0.0151 (6)0.0146 (6)0.0033 (5)0.0037 (5)0.0001 (5)
O20.0257 (7)0.0166 (6)0.0152 (6)0.0026 (5)0.0068 (5)0.0048 (5)
Cl10.0314 (3)0.0502 (4)0.0436 (3)0.0056 (3)0.0136 (2)0.0217 (3)
Geometric parameters (Å, º) top
C12—C111.384 (3)C14—H14B0.99
C12—C71.399 (3)N4—C171.496 (2)
C12—H120.95N4—C161.499 (2)
C11—C101.380 (3)N4—H40.89 (2)
C11—H110.95C16—C151.507 (2)
C10—C91.384 (3)C16—H16A0.99
C10—Cl11.743 (2)C16—H16B0.99
C9—C81.387 (3)C15—H15A0.99
C9—H90.95C15—H15B0.99
C8—C71.403 (3)C17—C181.520 (2)
C8—H80.95C17—H17A0.99
C7—C61.457 (3)C17—H17B0.99
C6—C51.346 (2)C18—O11.415 (2)
C6—H60.95C18—H18A0.99
C5—N11.399 (2)C18—H18B0.99
C5—C41.489 (2)O1—H10.92 (3)
N1—C21.309 (2)C20—C211.389 (3)
C2—N21.360 (2)C20—C191.390 (2)
C2—N31.392 (2)C20—H200.95
N3—C41.378 (2)C21—C221.380 (3)
N3—H30.94 (2)C21—H210.95
C4—O41.222 (2)C22—C231.383 (3)
N2—C151.468 (2)C22—H220.95
N2—C131.470 (2)C23—N51.344 (2)
C13—C141.514 (2)C23—H230.95
C13—H13A0.99N5—C191.344 (2)
C13—H13B0.99C19—C241.525 (2)
C14—N41.504 (2)C24—O21.245 (2)
C14—H14A0.99C24—O31.265 (2)
C11—C12—C7121.0 (2)C17—N4—C14113.32 (13)
C11—C12—H12119.5C16—N4—C14108.58 (13)
C7—C12—H12119.5C17—N4—H4108.3 (13)
C10—C11—C12119.29 (19)C16—N4—H4109.4 (13)
C10—C11—H11120.4C14—N4—H4107.5 (13)
C12—C11—H11120.4N4—C16—C15110.60 (14)
C11—C10—C9121.28 (18)N4—C16—H16A109.5
C11—C10—Cl1119.59 (16)C15—C16—H16A109.5
C9—C10—Cl1119.13 (17)N4—C16—H16B109.5
C10—C9—C8119.45 (19)C15—C16—H16B109.5
C10—C9—H9120.3H16A—C16—H16B108.1
C8—C9—H9120.3N2—C15—C16110.47 (14)
C9—C8—C7120.45 (18)N2—C15—H15A109.6
C9—C8—H8119.8C16—C15—H15A109.6
C7—C8—H8119.8N2—C15—H15B109.6
C12—C7—C8118.58 (18)C16—C15—H15B109.6
C12—C7—C6118.44 (18)H15A—C15—H15B108.1
C8—C7—C6122.95 (17)N4—C17—C18114.10 (14)
C5—C6—C7129.13 (17)N4—C17—H17A108.7
C5—C6—H6115.4C18—C17—H17A108.7
C7—C6—H6115.4N4—C17—H17B108.7
C6—C5—N1129.13 (16)C18—C17—H17B108.7
C6—C5—C4121.08 (16)H17A—C17—H17B107.6
N1—C5—C4109.13 (14)O1—C18—C17103.77 (14)
C2—N1—C5104.91 (14)O1—C18—H18A111
N1—C2—N2124.21 (16)C17—C18—H18A111
N1—C2—N3114.95 (15)O1—C18—H18B111
N2—C2—N3120.76 (15)C17—C18—H18B111
C4—N3—C2107.09 (14)H18A—C18—H18B109
C4—N3—H3121.8 (14)C18—O1—H1110.1 (16)
C2—N3—H3128.5 (14)C21—C20—C19119.33 (17)
O4—C4—N3125.95 (16)C21—C20—H20120.3
O4—C4—C5130.15 (16)C19—C20—H20120.3
N3—C4—C5103.87 (14)C22—C21—C20118.28 (18)
C2—N2—C15118.59 (14)C22—C21—H21120.9
C2—N2—C13115.54 (14)C20—C21—H21120.9
C15—N2—C13112.88 (13)C21—C22—C23118.67 (18)
N2—C13—C14110.43 (14)C21—C22—H22120.7
N2—C13—H13A109.6C23—C22—H22120.7
C14—C13—H13A109.6N5—C23—C22124.14 (18)
N2—C13—H13B109.6N5—C23—H23117.9
C14—C13—H13B109.6C22—C23—H23117.9
H13A—C13—H13B108.1C19—N5—C23116.69 (16)
N4—C14—C13110.32 (14)N5—C19—C20122.84 (16)
N4—C14—H14A109.6N5—C19—C24116.92 (15)
C13—C14—H14A109.6C20—C19—C24120.24 (15)
N4—C14—H14B109.6O2—C24—O3126.38 (16)
C13—C14—H14B109.6O2—C24—C19116.49 (15)
H14A—C14—H14B108.1O3—C24—C19117.13 (14)
C17—N4—C16109.63 (13)
C7—C12—C11—C100.8 (3)N1—C2—N2—C138.8 (2)
C12—C11—C10—C90.2 (3)N3—C2—N2—C13174.62 (15)
C12—C11—C10—Cl1179.37 (15)C2—N2—C13—C14163.72 (15)
C11—C10—C9—C80.8 (3)C15—N2—C13—C1455.26 (19)
Cl1—C10—C9—C8178.71 (14)N2—C13—C14—N456.92 (18)
C10—C9—C8—C70.6 (3)C13—C14—N4—C17178.91 (14)
C11—C12—C7—C81.0 (3)C13—C14—N4—C1659.02 (17)
C11—C12—C7—C6177.17 (17)C17—N4—C16—C15176.41 (14)
C9—C8—C7—C120.3 (3)C14—N4—C16—C1559.30 (17)
C9—C8—C7—C6177.75 (17)C2—N2—C15—C16164.89 (15)
C12—C7—C6—C5167.17 (19)C13—N2—C15—C1655.39 (18)
C8—C7—C6—C510.9 (3)N4—C16—C15—N257.32 (19)
C7—C6—C5—N11.0 (3)C16—N4—C17—C18168.08 (15)
C7—C6—C5—C4170.62 (17)C14—N4—C17—C1870.43 (19)
C6—C5—N1—C2168.27 (18)N4—C17—C18—O1173.10 (14)
C4—C5—N1—C22.37 (19)C19—C20—C21—C221.7 (3)
C5—N1—C2—N2178.77 (16)C20—C21—C22—C230.3 (3)
C5—N1—C2—N32.0 (2)C21—C22—C23—N51.5 (3)
N1—C2—N3—C40.8 (2)C22—C23—N5—C190.7 (3)
N2—C2—N3—C4177.68 (15)C23—N5—C19—C201.4 (3)
C2—N3—C4—O4178.92 (17)C23—N5—C19—C24177.84 (16)
C2—N3—C4—C50.73 (17)C21—C20—C19—N52.6 (3)
C6—C5—C4—O48.5 (3)C21—C20—C19—C24176.59 (16)
N1—C5—C4—O4179.99 (17)N5—C19—C24—O2177.51 (15)
C6—C5—C4—N3169.60 (16)C20—C19—C24—O21.8 (2)
N1—C5—C4—N31.93 (18)N5—C19—C24—O32.0 (2)
N1—C2—N2—C15147.47 (17)C20—C19—C24—O3178.70 (16)
N3—C2—N2—C1535.9 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C13—H13B···O4i0.992.643.287 (2)123
C13—H13B···O30.992.643.302 (2)124
C14—H14B···O4ii0.992.453.299 (2)144
C16—H16A···O4ii0.992.523.359 (2)142
C16—H16B···O2iii0.992.613.202 (2)119
C15—H15A···O1iv0.992.373.091 (2)129
C15—H15B···O3v0.992.493.422 (2)157
C17—H17B···O4ii0.992.473.317 (2)144
C18—H18A···O30.992.63.249 (2)123
C22—H22···N5vi0.952.583.402 (2)145
N3—H3···O3v0.94 (2)1.86 (2)2.796 (2)173 (2)
N4—H4···N50.89 (2)2.38 (2)3.095 (2)137 (2)
N4—H4···O30.89 (2)1.96 (2)2.747 (2)147 (2)
O1—H1···O2vii0.92 (3)1.80 (3)2.704 (2)166 (2)
Symmetry codes: (i) x, y1, z; (ii) x, y+1/2, z+1/2; (iii) x, y1/2, z+1/2; (iv) x, y1/2, z1/2; (v) x, y+1, z; (vi) x, y+1/2, z+1/2; (vii) x, y3/2, z+1/2.
4-[(Z)-4-(4-Chlorobenzylidene)-5-oxo-3,4-dihydro-1H-imidazol-2-yl]-1-(2-hydroxyethyl)piperazin-1-ium 2-(4-nitrophenyl)acetate (3b) top
Crystal data top
C16H20ClN4O2+·C8H6NO4Z = 2
Mr = 515.95F(000) = 540
Triclinic, P1Dx = 1.395 Mg m3
Hall symbol: -P 1Cu Kα radiation, λ = 1.54184 Å
a = 7.8667 (4) ÅCell parameters from 4966 reflections
b = 11.9015 (7) Åθ = 3.3–71.8°
c = 14.4406 (9) ŵ = 1.81 mm1
α = 66.859 (6)°T = 298 K
β = 85.085 (4)°Block, colourless
γ = 81.332 (5)°0.49 × 0.17 × 0.14 mm
V = 1228.51 (13) Å3
Data collection top
Rigaku SuperNova Dual Source
diffractometer with an Atlas detector
4750 independent reflections
Radiation source: micro-focus sealed X-ray tube3217 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.072
Detector resolution: 10.3756 pixels mm-1θmax = 71.8°, θmin = 3.3°
ω scansh = 99
Absorption correction: gaussian
(CrysAlis PRO; Rigaku OD, 2015)
k = 1414
Tmin = 0.824, Tmax = 0.947l = 1717
17827 measured reflections
Refinement top
Refinement on F2Hydrogen site location: mixed
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.068 w = 1/[σ2(Fo2) + (0.1334P)2 + 0.0797P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.223(Δ/σ)max = 0.001
S = 1.03Δρmax = 0.24 e Å3
4750 reflectionsΔρmin = 0.40 e Å3
354 parametersExtinction correction: SHELXL2013 (Sheldrick, 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
2 restraintsExtinction coefficient: 0.0034 (10)
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
C20.9074 (3)1.1563 (2)0.8711 (2)0.0626 (6)
C41.1738 (4)1.1112 (3)0.8186 (2)0.0702 (7)
C51.0437 (3)1.0585 (2)0.7838 (2)0.0656 (7)
C61.0850 (4)1.0010 (3)0.7199 (2)0.0696 (7)
H61.20170.98780.70480.084*
C70.9712 (4)0.9568 (2)0.6713 (2)0.0662 (7)
C80.7925 (4)0.9911 (3)0.6676 (2)0.0710 (7)
H80.7421.0450.69740.085*
C90.6915 (4)0.9464 (3)0.6208 (2)0.0772 (8)
H90.57350.97130.61780.093*
C100.7647 (5)0.8637 (3)0.5775 (3)0.0815 (9)
C110.9421 (5)0.8314 (3)0.5774 (2)0.0811 (9)
H110.99220.77850.54660.097*
C121.0424 (4)0.8781 (3)0.6230 (2)0.0741 (8)
H121.16110.8570.6220.089*
C130.6051 (3)1.1853 (3)0.9131 (3)0.0732 (8)
H13A0.60251.11320.89790.088*
H13B0.55231.25670.85840.088*
C140.5053 (3)1.1712 (3)1.0105 (2)0.0681 (7)
H14A0.38611.16511.0030.082*
H14B0.55221.09581.06390.082*
C150.7990 (4)1.3020 (3)0.9521 (3)0.0716 (8)
H15A0.75671.37940.89920.086*
H15B0.91921.30370.96130.086*
C160.6990 (3)1.2885 (3)1.0478 (2)0.0691 (7)
H16A0.70581.35931.06420.083*
H16B0.7491.21551.10220.083*
C170.4154 (4)1.2688 (3)1.1355 (2)0.0777 (8)
H17A0.45451.191.18790.093*
H17B0.4431.33271.15540.093*
C180.2232 (4)1.2802 (3)1.1300 (3)0.0772 (8)
H18A0.19551.22441.10110.093*
H18B0.17331.25511.19780.093*
C190.0993 (4)1.4825 (3)0.6908 (2)0.0650 (7)
C200.0722 (4)1.5135 (3)0.7117 (3)0.0760 (8)
H200.10091.56390.74770.091*
C210.2001 (4)1.4717 (3)0.6807 (3)0.0769 (8)
H210.31491.49380.69490.092*
C220.1570 (4)1.3968 (3)0.6282 (2)0.0681 (7)
C230.0123 (4)1.3635 (3)0.6064 (2)0.0717 (7)
H230.04011.31290.57060.086*
C240.1395 (4)1.4060 (3)0.6384 (2)0.0721 (7)
H240.25421.38310.62470.087*
C250.2391 (4)1.5278 (3)0.7276 (2)0.0795 (9)
H25A0.34111.52750.68490.095*
H25B0.20181.61250.71960.095*
C260.2878 (3)1.4542 (2)0.8359 (2)0.0608 (6)
N10.8816 (3)1.0881 (2)0.82195 (19)0.0672 (6)
N20.7835 (3)1.2002 (2)0.9222 (2)0.0724 (7)
N31.0772 (3)1.1742 (2)0.8716 (2)0.0676 (6)
H31.113 (5)1.232 (4)0.888 (3)0.101*
N40.5142 (3)1.2783 (2)1.03857 (17)0.0606 (5)
HN40.467 (4)1.351 (3)0.985 (3)0.091*
N50.2917 (4)1.3529 (3)0.5927 (3)0.0880 (8)
O10.1482 (3)1.4005 (2)1.0724 (2)0.0936 (7)
H10.153 (6)1.406 (5)1.005 (4)0.14*
O20.1998 (2)1.37064 (18)0.89135 (14)0.0682 (5)
O30.4151 (3)1.48002 (18)0.86656 (15)0.0730 (6)
O41.3296 (3)1.1026 (2)0.8054 (2)0.0896 (7)
O5A0.243 (5)1.327 (4)0.525 (3)0.121 (11)0.22 (4)
O6A0.426 (3)1.339 (2)0.6425 (14)0.077 (8)0.22 (4)
O5B0.2577 (10)1.2940 (12)0.5389 (8)0.094 (2)0.78 (4)
O6B0.4396 (12)1.384 (3)0.6129 (19)0.178 (5)0.78 (4)
Cl10.63520 (16)0.80286 (10)0.52260 (9)0.1174 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C20.0546 (13)0.0636 (15)0.0742 (17)0.0137 (11)0.0018 (12)0.0291 (13)
C40.0575 (15)0.0651 (16)0.086 (2)0.0105 (12)0.0053 (13)0.0257 (15)
C50.0573 (14)0.0573 (14)0.0815 (19)0.0095 (11)0.0005 (13)0.0255 (13)
C60.0609 (15)0.0611 (15)0.084 (2)0.0092 (12)0.0060 (13)0.0264 (14)
C70.0714 (16)0.0550 (14)0.0698 (17)0.0135 (12)0.0040 (13)0.0207 (13)
C80.0756 (17)0.0631 (16)0.0735 (18)0.0097 (13)0.0002 (14)0.0257 (14)
C90.0802 (19)0.0676 (17)0.078 (2)0.0080 (14)0.0118 (15)0.0201 (15)
C100.106 (2)0.0659 (17)0.0721 (19)0.0131 (16)0.0172 (17)0.0224 (15)
C110.104 (2)0.0700 (18)0.0718 (19)0.0047 (16)0.0038 (17)0.0318 (15)
C120.0824 (19)0.0645 (16)0.0711 (18)0.0083 (14)0.0070 (15)0.0239 (14)
C130.0546 (14)0.0827 (19)0.102 (2)0.0168 (13)0.0014 (14)0.0542 (18)
C140.0569 (14)0.0624 (15)0.091 (2)0.0144 (11)0.0015 (13)0.0338 (14)
C150.0623 (15)0.0812 (18)0.091 (2)0.0264 (13)0.0052 (14)0.0499 (16)
C160.0607 (15)0.0759 (17)0.0800 (19)0.0146 (13)0.0098 (13)0.0364 (15)
C170.085 (2)0.085 (2)0.0613 (17)0.0244 (16)0.0035 (14)0.0229 (15)
C180.0805 (19)0.0786 (19)0.0745 (19)0.0179 (15)0.0145 (15)0.0323 (16)
C190.0673 (15)0.0641 (15)0.0599 (15)0.0189 (12)0.0107 (12)0.0145 (12)
C200.0783 (19)0.0770 (19)0.082 (2)0.0122 (15)0.0031 (15)0.0398 (16)
C210.0594 (15)0.086 (2)0.092 (2)0.0087 (14)0.0016 (14)0.0420 (18)
C220.0587 (15)0.0784 (18)0.0706 (17)0.0147 (13)0.0093 (12)0.0286 (14)
C230.0671 (16)0.0839 (19)0.0711 (18)0.0111 (14)0.0064 (13)0.0358 (15)
C240.0554 (14)0.0868 (19)0.0765 (18)0.0104 (13)0.0073 (13)0.0323 (15)
C250.086 (2)0.0771 (19)0.0735 (19)0.0308 (16)0.0164 (15)0.0162 (15)
C260.0618 (14)0.0585 (14)0.0685 (16)0.0132 (11)0.0060 (12)0.0285 (12)
N10.0578 (12)0.0684 (13)0.0858 (16)0.0156 (10)0.0016 (11)0.0387 (12)
N20.0569 (12)0.0843 (16)0.0986 (18)0.0222 (11)0.0038 (12)0.0559 (14)
N30.0540 (12)0.0706 (14)0.0857 (16)0.0151 (10)0.0066 (11)0.0349 (12)
N40.0613 (12)0.0617 (13)0.0612 (13)0.0144 (10)0.0004 (10)0.0243 (10)
N50.0676 (16)0.108 (2)0.101 (2)0.0238 (15)0.0094 (16)0.0481 (18)
O10.1076 (18)0.0878 (16)0.0816 (15)0.0015 (13)0.0005 (13)0.0341 (13)
O20.0682 (11)0.0745 (12)0.0656 (11)0.0260 (9)0.0036 (9)0.0246 (9)
O30.0737 (12)0.0732 (12)0.0765 (13)0.0263 (9)0.0162 (10)0.0248 (10)
O40.0538 (11)0.1030 (17)0.1184 (19)0.0120 (10)0.0037 (11)0.0485 (15)
O5A0.18 (3)0.14 (2)0.081 (12)0.110 (19)0.023 (12)0.066 (13)
O6A0.062 (10)0.101 (13)0.076 (14)0.038 (7)0.012 (6)0.036 (10)
O5B0.089 (3)0.106 (5)0.109 (4)0.035 (3)0.015 (3)0.053 (4)
O6B0.061 (3)0.269 (13)0.284 (12)0.026 (6)0.007 (6)0.190 (10)
Cl10.1404 (10)0.1029 (7)0.1250 (9)0.0017 (6)0.0550 (7)0.0556 (6)
Geometric parameters (Å, º) top
C2—N11.316 (3)C16—H16A0.97
C2—N21.339 (4)C16—H16B0.97
C2—N31.385 (3)C17—C181.504 (4)
C4—O41.218 (3)C17—N41.514 (4)
C4—N31.380 (4)C17—H17A0.97
C4—C51.491 (4)C17—H17B0.97
C5—C61.342 (4)C18—O11.408 (4)
C5—N11.396 (4)C18—H18A0.97
C6—C71.454 (4)C18—H18B0.97
C6—H60.93C19—C201.384 (4)
C7—C81.402 (4)C19—C241.384 (4)
C7—C121.402 (4)C19—C251.512 (4)
C8—C91.369 (4)C20—C211.365 (4)
C8—H80.93C20—H200.93
C9—C101.394 (5)C21—C221.371 (4)
C9—H90.93C21—H210.93
C10—C111.391 (5)C22—C231.377 (4)
C10—Cl11.733 (3)C22—N51.460 (4)
C11—C121.369 (5)C23—C241.373 (4)
C11—H110.93C23—H230.93
C12—H120.93C24—H240.93
C13—N21.464 (3)C25—C261.511 (4)
C13—C141.512 (4)C25—H25A0.97
C13—H13A0.97C25—H25B0.97
C13—H13B0.97C26—O31.253 (3)
C14—N41.494 (3)C26—O21.263 (3)
C14—H14A0.97N3—H30.90 (4)
C14—H14B0.97N4—HN40.95 (4)
C15—N21.461 (3)N5—O5A1.15 (3)
C15—C161.494 (4)N5—O6B1.212 (10)
C15—H15A0.97N5—O6A1.22 (2)
C15—H15B0.97N5—O5B1.227 (10)
C16—N41.498 (3)O1—H10.94 (5)
N1—C2—N2123.9 (2)C18—C17—H17B108.5
N1—C2—N3114.7 (3)N4—C17—H17B108.5
N2—C2—N3121.3 (2)H17A—C17—H17B107.5
O4—C4—N3126.4 (3)O1—C18—C17113.3 (3)
O4—C4—C5129.8 (3)O1—C18—H18A108.9
N3—C4—C5103.8 (2)C17—C18—H18A108.9
C6—C5—N1128.8 (3)O1—C18—H18B108.9
C6—C5—C4122.1 (3)C17—C18—H18B108.9
N1—C5—C4108.9 (2)H18A—C18—H18B107.7
C5—C6—C7128.5 (3)C20—C19—C24118.4 (3)
C5—C6—H6115.8C20—C19—C25120.6 (3)
C7—C6—H6115.8C24—C19—C25121.0 (3)
C8—C7—C12117.6 (3)C21—C20—C19121.5 (3)
C8—C7—C6123.4 (3)C21—C20—H20119.3
C12—C7—C6118.9 (3)C19—C20—H20119.3
C9—C8—C7120.9 (3)C20—C21—C22119.0 (3)
C9—C8—H8119.5C20—C21—H21120.5
C7—C8—H8119.5C22—C21—H21120.5
C8—C9—C10120.3 (3)C21—C22—C23121.2 (3)
C8—C9—H9119.9C21—C22—N5120.0 (3)
C10—C9—H9119.9C23—C22—N5118.9 (3)
C11—C10—C9119.8 (3)C24—C23—C22119.1 (3)
C11—C10—Cl1120.1 (3)C24—C23—H23120.4
C9—C10—Cl1120.1 (3)C22—C23—H23120.4
C12—C11—C10119.5 (3)C23—C24—C19120.9 (3)
C12—C11—H11120.3C23—C24—H24119.6
C10—C11—H11120.3C19—C24—H24119.6
C11—C12—C7121.8 (3)C26—C25—C19115.4 (2)
C11—C12—H12119.1C26—C25—H25A108.4
C7—C12—H12119.1C19—C25—H25A108.4
N2—C13—C14109.9 (2)C26—C25—H25B108.4
N2—C13—H13A109.7C19—C25—H25B108.4
C14—C13—H13A109.7H25A—C25—H25B107.5
N2—C13—H13B109.7O3—C26—O2122.9 (3)
C14—C13—H13B109.7O3—C26—C25117.6 (2)
H13A—C13—H13B108.2O2—C26—C25119.5 (2)
N4—C14—C13110.9 (2)C2—N1—C5105.1 (2)
N4—C14—H14A109.5C2—N2—C15123.4 (2)
C13—C14—H14A109.5C2—N2—C13118.6 (2)
N4—C14—H14B109.5C15—N2—C13113.3 (2)
C13—C14—H14B109.5C4—N3—C2107.4 (2)
H14A—C14—H14B108C4—N3—H3125 (2)
N2—C15—C16110.8 (2)C2—N3—H3126 (2)
N2—C15—H15A109.5C14—N4—C16109.0 (2)
C16—C15—H15A109.5C14—N4—C17113.0 (2)
N2—C15—H15B109.5C16—N4—C17109.8 (2)
C16—C15—H15B109.5C14—N4—HN4108 (2)
H15A—C15—H15B108.1C16—N4—HN4108 (2)
C15—C16—N4111.2 (2)C17—N4—HN4109 (2)
C15—C16—H16A109.4O5A—N5—O6A131 (2)
N4—C16—H16A109.4O6B—N5—O5B121.0 (7)
C15—C16—H16B109.4O5A—N5—C22111.1 (18)
N4—C16—H16B109.4O6B—N5—C22117.5 (6)
H16A—C16—H16B108O6A—N5—C22117.2 (11)
C18—C17—N4115.0 (3)O5B—N5—C22121.4 (5)
C18—C17—H17A108.5C18—O1—H1106 (3)
N4—C17—H17A108.5
O4—C4—C5—C67.5 (5)C19—C25—C26—O3172.6 (3)
N3—C4—C5—C6172.7 (3)C19—C25—C26—O27.7 (4)
O4—C4—C5—N1176.9 (3)N2—C2—N1—C5177.5 (3)
N3—C4—C5—N12.9 (3)N3—C2—N1—C51.3 (3)
N1—C5—C6—C71.7 (5)C6—C5—N1—C2172.7 (3)
C4—C5—C6—C7172.9 (3)C4—C5—N1—C22.5 (3)
C5—C6—C7—C814.1 (5)N1—C2—N2—C15162.1 (3)
C5—C6—C7—C12167.6 (3)N3—C2—N2—C1521.9 (5)
C12—C7—C8—C91.7 (4)N1—C2—N2—C138.1 (5)
C6—C7—C8—C9180.0 (3)N3—C2—N2—C13176.0 (3)
C7—C8—C9—C101.3 (5)C16—C15—N2—C2149.5 (3)
C8—C9—C10—C113.3 (5)C16—C15—N2—C1355.3 (4)
C8—C9—C10—Cl1177.5 (2)C14—C13—N2—C2148.2 (3)
C9—C10—C11—C122.3 (5)C14—C13—N2—C1555.3 (3)
Cl1—C10—C11—C12178.6 (2)O4—C4—N3—C2177.8 (3)
C10—C11—C12—C70.8 (5)C5—C4—N3—C22.0 (3)
C8—C7—C12—C112.8 (4)N1—C2—N3—C40.5 (4)
C6—C7—C12—C11178.8 (3)N2—C2—N3—C4175.8 (3)
N2—C13—C14—N456.6 (3)C13—C14—N4—C1657.9 (3)
N2—C15—C16—N455.9 (3)C13—C14—N4—C17179.7 (2)
N4—C17—C18—O171.1 (4)C15—C16—N4—C1457.5 (3)
C24—C19—C20—C210.9 (5)C15—C16—N4—C17178.2 (2)
C25—C19—C20—C21178.8 (3)C18—C17—N4—C1468.3 (3)
C19—C20—C21—C220.4 (5)C18—C17—N4—C16169.8 (3)
C20—C21—C22—C230.1 (5)C21—C22—N5—O5A156 (2)
C20—C21—C22—N5178.9 (3)C23—C22—N5—O5A22 (2)
C21—C22—C23—C240.2 (5)C21—C22—N5—O6B1.1 (17)
N5—C22—C23—C24179.1 (3)C23—C22—N5—O6B180.0 (16)
C22—C23—C24—C190.7 (5)C21—C22—N5—O6A30.0 (13)
C20—C19—C24—C231.0 (4)C23—C22—N5—O6A151.2 (13)
C25—C19—C24—C23179.0 (3)C21—C22—N5—O5B174.1 (8)
C20—C19—C25—C2681.5 (4)C23—C22—N5—O5B4.7 (9)
C24—C19—C25—C2696.4 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C11—H11···O5Ai0.932.543.41 (4)154
C11—H11···O5Bi0.932.553.37 (1)148
C13—H13A···O4ii0.972.673.242 (4)118
C14—H14A···O20.972.643.186 (4)116
C14—H14B···O4iii0.972.483.446 (4)177
C15—H15B···O2iv0.972.463.334 (3)150
C16—H16A···O3v0.972.523.416 (4)153
C17—H17B···O3v0.972.543.441 (4)155
C20—H20···O1vi0.932.783.624 (4)152
C24—H24···O6Aiv0.932.513.39 (3)159
C24—H24···O6Biv0.932.403.282 (9)158
C25—H25A···O6Biv0.972.683.505 (12)143
N3—H3···O2iv0.90 (4)1.89 (4)2.781 (3)168 (4)
N4—HN4···O20.95 (4)2.53 (4)3.177 (3)125 (3)
N4—HN4···O30.95 (4)1.82 (4)2.761 (3)168 (3)
O1—H1···O20.94 (5)1.85 (5)2.762 (3)163 (5)
Symmetry codes: (i) x+1, y+2, z+1; (ii) x1, y, z; (iii) x+2, y+2, z+2; (iv) x+1, y, z; (v) x+1, y+3, z+2; (vi) x, y+3, z+2.
 

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