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

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.

Computing details

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)

Crystal data

C16H20ClN4O2^+·C6H4NO2^−	F(000) = 960
Mr = 457.91	Dx = 1.42 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7626 reflections
a = 22.6220 (4) Å	θ = 1.0–27.5°
b = 7.1937 (2) Å	µ = 0.22 mm^−1
c = 13.5315 (7) Å	T = 120 K
β = 103.499 (2)°	Plate, colourless
V = 2141.23 (13) Å^3	0.39 × 0.35 × 0.11 mm
Z = 4

Data collection

Bruker KappaCCD diffractometer	4720 independent reflections
Horizonally mounted graphite crystal monochromator	3651 reflections with I > 2σ(I)
Detector resolution: 9 pixels mm^-1	Rint = 0.045
CCD scans	θmax = 27.2°, θmin = 3.0°
Absorption correction: multi-scan (DENZO-SMN; Otwinowski & Minor, 1997)	h = −28→29
Tmin = 0.901, Tmax = 1.000	k = −9→9
14522 measured reflections	l = −17→17

Refinement

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.043	w = 1/[σ^2(Fo^2) + (0.036P)^2 + 1.8941P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.103	(Δ/σ)max < 0.001
S = 1.02	Δρmax = 0.60 e Å^−3
4720 reflections	Δρmin = −0.6 e Å^−3
302 parameters	Extinction correction: SHELXL2014 (Sheldrick, 2015), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0045 (9)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
C12	0.40993 (9)	0.1213 (3)	−0.08873 (15)	0.0256 (4)
H12	0.404	0.2415	−0.1184	0.031*
C11	0.43467 (9)	−0.0182 (3)	−0.13694 (16)	0.0305 (5)
H11	0.4452	0.0055	−0.1997	0.037*
C10	0.44382 (8)	−0.1919 (3)	−0.09286 (16)	0.0272 (5)
C9	0.42888 (8)	−0.2292 (3)	−0.00131 (16)	0.0256 (4)
H9	0.4359	−0.3492	0.0285	0.031*
C8	0.40350 (8)	−0.0900 (3)	0.04651 (15)	0.0222 (4)
H8	0.3928	−0.1152	0.1091	0.027*
C7	0.39348 (8)	0.0877 (3)	0.00314 (14)	0.0201 (4)
C6	0.36503 (8)	0.2375 (3)	0.04789 (14)	0.0189 (4)
H6	0.3672	0.3571	0.0192	0.023*
C5	0.33611 (8)	0.2303 (2)	0.12419 (13)	0.0162 (4)
N1	0.32477 (7)	0.0767 (2)	0.18039 (11)	0.0166 (3)
C2	0.28577 (8)	0.1363 (2)	0.23098 (13)	0.0140 (3)
N3	0.27035 (7)	0.3234 (2)	0.21673 (11)	0.0149 (3)
C4	0.30176 (8)	0.3934 (2)	0.14909 (13)	0.0157 (4)
O4	0.29908 (6)	0.55285 (17)	0.11713 (9)	0.0198 (3)
N2	0.26329 (6)	0.03067 (19)	0.29710 (11)	0.0145 (3)
C13	0.27837 (8)	−0.1682 (2)	0.29849 (13)	0.0158 (4)
H13A	0.3216	−0.1834	0.2967	0.019*
H13B	0.2531	−0.2294	0.2375	0.019*
C14	0.26716 (8)	−0.2596 (2)	0.39329 (13)	0.0156 (4)
H14A	0.2759	−0.3943	0.3919	0.019*
H14B	0.2948	−0.2055	0.4541	0.019*
N4	0.20229 (7)	−0.2312 (2)	0.39956 (11)	0.0134 (3)
C16	0.19018 (8)	−0.0265 (2)	0.40117 (13)	0.0151 (4)
H16A	0.2172	0.0298	0.462	0.018*
H16B	0.1476	−0.0055	0.4054	0.018*
C15	0.20093 (8)	0.0653 (2)	0.30678 (13)	0.0148 (4)
H15A	0.1717	0.0158	0.2463	0.018*
H15B	0.1941	0.2008	0.3101	0.018*
C17	0.18754 (8)	−0.3210 (2)	0.49056 (13)	0.0167 (4)
H17A	0.1475	−0.2748	0.4978	0.02*
H17B	0.2183	−0.2825	0.5519	0.02*
C18	0.18561 (8)	−0.5321 (2)	0.48602 (13)	0.0166 (4)
H18A	0.1577	−0.5758	0.4226	0.02*
H18B	0.2266	−0.5843	0.4899	0.02*
O1	0.16389 (6)	−0.58317 (19)	0.57220 (9)	0.0218 (3)
C20	0.03275 (8)	−0.3026 (2)	0.06731 (14)	0.0179 (4)
H20	0.0343	−0.3708	0.0078	0.021*
C21	−0.01453 (9)	−0.1790 (3)	0.06659 (15)	0.0238 (4)
H21	−0.0464	−0.1634	0.0075	0.029*
C22	−0.01401 (9)	−0.0794 (3)	0.15396 (16)	0.0273 (5)
H22	−0.0457	0.006	0.1564	0.033*
C23	0.03350 (9)	−0.1064 (3)	0.23782 (15)	0.0248 (4)
H23	0.0339	−0.0348	0.297	0.03*
N5	0.07913 (7)	−0.2275 (2)	0.24095 (11)	0.0178 (3)
C19	0.07778 (8)	−0.3255 (2)	0.15591 (13)	0.0137 (3)
C24	0.12818 (8)	−0.4683 (2)	0.16024 (13)	0.0139 (4)
O3	0.16842 (5)	−0.47981 (17)	0.24246 (9)	0.0161 (3)
O2	0.12535 (6)	−0.56308 (17)	0.08229 (9)	0.0188 (3)
Cl1	0.47425 (3)	−0.36900 (9)	−0.15369 (4)	0.04095 (18)
H3	0.2369 (11)	0.386 (3)	0.2308 (17)	0.035 (6)*
H4	0.1785 (10)	−0.281 (3)	0.3439 (16)	0.020 (5)*
H1	0.1558 (12)	−0.709 (4)	0.5709 (19)	0.049 (8)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C12	0.0216 (10)	0.0325 (11)	0.0258 (10)	−0.0036 (8)	0.0118 (8)	0.0002 (9)
C11	0.0218 (10)	0.0474 (14)	0.0262 (11)	−0.0049 (9)	0.0133 (8)	−0.0066 (10)
C10	0.0148 (9)	0.0370 (12)	0.0313 (11)	0.0005 (8)	0.0081 (8)	−0.0134 (9)
C9	0.0175 (9)	0.0263 (10)	0.0330 (11)	0.0016 (8)	0.0061 (8)	−0.0044 (9)
C8	0.0178 (9)	0.0258 (10)	0.0240 (10)	−0.0002 (8)	0.0067 (8)	−0.0014 (8)
C7	0.0131 (8)	0.0274 (10)	0.0216 (9)	−0.0035 (7)	0.0074 (7)	−0.0026 (8)
C6	0.0167 (9)	0.0180 (9)	0.0230 (10)	−0.0021 (7)	0.0066 (7)	0.0023 (7)
C5	0.0158 (8)	0.0142 (8)	0.0189 (9)	0.0000 (7)	0.0045 (7)	0.0010 (7)
N1	0.0168 (7)	0.0158 (7)	0.0185 (8)	0.0003 (6)	0.0070 (6)	0.0021 (6)
C2	0.0143 (8)	0.0134 (8)	0.0143 (8)	0.0000 (7)	0.0036 (6)	0.0003 (7)
N3	0.0164 (7)	0.0126 (7)	0.0171 (7)	0.0018 (6)	0.0067 (6)	0.0014 (6)
C4	0.0162 (8)	0.0171 (9)	0.0134 (8)	−0.0008 (7)	0.0025 (7)	0.0010 (7)
O4	0.0271 (7)	0.0140 (6)	0.0200 (7)	0.0005 (5)	0.0087 (5)	0.0041 (5)
N2	0.0176 (7)	0.0111 (7)	0.0168 (7)	0.0022 (6)	0.0081 (6)	0.0024 (6)
C13	0.0211 (9)	0.0102 (8)	0.0183 (9)	0.0027 (7)	0.0093 (7)	0.0009 (7)
C14	0.0171 (9)	0.0137 (8)	0.0169 (9)	0.0019 (7)	0.0056 (7)	0.0016 (7)
N4	0.0196 (8)	0.0115 (7)	0.0100 (7)	−0.0005 (6)	0.0057 (6)	0.0006 (6)
C16	0.0210 (9)	0.0110 (8)	0.0148 (8)	0.0015 (7)	0.0074 (7)	0.0005 (7)
C15	0.0184 (9)	0.0121 (8)	0.0160 (8)	0.0021 (7)	0.0081 (7)	0.0024 (7)
C17	0.0258 (9)	0.0151 (9)	0.0114 (8)	−0.0015 (7)	0.0087 (7)	0.0015 (7)
C18	0.0216 (9)	0.0149 (9)	0.0146 (8)	−0.0005 (7)	0.0069 (7)	0.0025 (7)
O1	0.0350 (8)	0.0174 (7)	0.0158 (6)	−0.0062 (6)	0.0114 (6)	0.0015 (5)
C20	0.0195 (9)	0.0157 (9)	0.0187 (9)	−0.0035 (7)	0.0049 (7)	−0.0023 (7)
C21	0.0184 (9)	0.0192 (10)	0.0307 (11)	0.0005 (8)	−0.0003 (8)	0.0022 (8)
C22	0.0228 (10)	0.0210 (10)	0.0383 (12)	0.0067 (8)	0.0076 (9)	−0.0042 (9)
C23	0.0258 (10)	0.0214 (10)	0.0286 (11)	0.0053 (8)	0.0093 (8)	−0.0080 (8)
N5	0.0213 (8)	0.0153 (7)	0.0182 (8)	0.0010 (6)	0.0074 (6)	−0.0038 (6)
C19	0.0173 (8)	0.0108 (8)	0.0148 (8)	−0.0017 (7)	0.0074 (7)	−0.0003 (6)
C24	0.0170 (8)	0.0109 (8)	0.0157 (9)	−0.0027 (6)	0.0078 (7)	0.0011 (7)
O3	0.0186 (6)	0.0151 (6)	0.0146 (6)	0.0033 (5)	0.0037 (5)	0.0001 (5)
O2	0.0257 (7)	0.0166 (6)	0.0152 (6)	0.0026 (5)	0.0068 (5)	−0.0048 (5)
Cl1	0.0314 (3)	0.0502 (4)	0.0436 (3)	0.0056 (3)	0.0136 (2)	−0.0217 (3)

Geometric parameters (Å, º)

C12—C11	1.384 (3)	C14—H14B	0.99
C12—C7	1.399 (3)	N4—C17	1.496 (2)
C12—H12	0.95	N4—C16	1.499 (2)
C11—C10	1.380 (3)	N4—H4	0.89 (2)
C11—H11	0.95	C16—C15	1.507 (2)
C10—C9	1.384 (3)	C16—H16A	0.99
C10—Cl1	1.743 (2)	C16—H16B	0.99
C9—C8	1.387 (3)	C15—H15A	0.99
C9—H9	0.95	C15—H15B	0.99
C8—C7	1.403 (3)	C17—C18	1.520 (2)
C8—H8	0.95	C17—H17A	0.99
C7—C6	1.457 (3)	C17—H17B	0.99
C6—C5	1.346 (2)	C18—O1	1.415 (2)
C6—H6	0.95	C18—H18A	0.99
C5—N1	1.399 (2)	C18—H18B	0.99
C5—C4	1.489 (2)	O1—H1	0.92 (3)
N1—C2	1.309 (2)	C20—C21	1.389 (3)
C2—N2	1.360 (2)	C20—C19	1.390 (2)
C2—N3	1.392 (2)	C20—H20	0.95
N3—C4	1.378 (2)	C21—C22	1.380 (3)
N3—H3	0.94 (2)	C21—H21	0.95
C4—O4	1.222 (2)	C22—C23	1.383 (3)
N2—C15	1.468 (2)	C22—H22	0.95
N2—C13	1.470 (2)	C23—N5	1.344 (2)
C13—C14	1.514 (2)	C23—H23	0.95
C13—H13A	0.99	N5—C19	1.344 (2)
C13—H13B	0.99	C19—C24	1.525 (2)
C14—N4	1.504 (2)	C24—O2	1.245 (2)
C14—H14A	0.99	C24—O3	1.265 (2)
C11—C12—C7	121.0 (2)	C17—N4—C14	113.32 (13)
C11—C12—H12	119.5	C16—N4—C14	108.58 (13)
C7—C12—H12	119.5	C17—N4—H4	108.3 (13)
C10—C11—C12	119.29 (19)	C16—N4—H4	109.4 (13)
C10—C11—H11	120.4	C14—N4—H4	107.5 (13)
C12—C11—H11	120.4	N4—C16—C15	110.60 (14)
C11—C10—C9	121.28 (18)	N4—C16—H16A	109.5
C11—C10—Cl1	119.59 (16)	C15—C16—H16A	109.5
C9—C10—Cl1	119.13 (17)	N4—C16—H16B	109.5
C10—C9—C8	119.45 (19)	C15—C16—H16B	109.5
C10—C9—H9	120.3	H16A—C16—H16B	108.1
C8—C9—H9	120.3	N2—C15—C16	110.47 (14)
C9—C8—C7	120.45 (18)	N2—C15—H15A	109.6
C9—C8—H8	119.8	C16—C15—H15A	109.6
C7—C8—H8	119.8	N2—C15—H15B	109.6
C12—C7—C8	118.58 (18)	C16—C15—H15B	109.6
C12—C7—C6	118.44 (18)	H15A—C15—H15B	108.1
C8—C7—C6	122.95 (17)	N4—C17—C18	114.10 (14)
C5—C6—C7	129.13 (17)	N4—C17—H17A	108.7
C5—C6—H6	115.4	C18—C17—H17A	108.7
C7—C6—H6	115.4	N4—C17—H17B	108.7
C6—C5—N1	129.13 (16)	C18—C17—H17B	108.7
C6—C5—C4	121.08 (16)	H17A—C17—H17B	107.6
N1—C5—C4	109.13 (14)	O1—C18—C17	103.77 (14)
C2—N1—C5	104.91 (14)	O1—C18—H18A	111
N1—C2—N2	124.21 (16)	C17—C18—H18A	111
N1—C2—N3	114.95 (15)	O1—C18—H18B	111
N2—C2—N3	120.76 (15)	C17—C18—H18B	111
C4—N3—C2	107.09 (14)	H18A—C18—H18B	109
C4—N3—H3	121.8 (14)	C18—O1—H1	110.1 (16)
C2—N3—H3	128.5 (14)	C21—C20—C19	119.33 (17)
O4—C4—N3	125.95 (16)	C21—C20—H20	120.3
O4—C4—C5	130.15 (16)	C19—C20—H20	120.3
N3—C4—C5	103.87 (14)	C22—C21—C20	118.28 (18)
C2—N2—C15	118.59 (14)	C22—C21—H21	120.9
C2—N2—C13	115.54 (14)	C20—C21—H21	120.9
C15—N2—C13	112.88 (13)	C21—C22—C23	118.67 (18)
N2—C13—C14	110.43 (14)	C21—C22—H22	120.7
N2—C13—H13A	109.6	C23—C22—H22	120.7
C14—C13—H13A	109.6	N5—C23—C22	124.14 (18)
N2—C13—H13B	109.6	N5—C23—H23	117.9
C14—C13—H13B	109.6	C22—C23—H23	117.9
H13A—C13—H13B	108.1	C19—N5—C23	116.69 (16)
N4—C14—C13	110.32 (14)	N5—C19—C20	122.84 (16)
N4—C14—H14A	109.6	N5—C19—C24	116.92 (15)
C13—C14—H14A	109.6	C20—C19—C24	120.24 (15)
N4—C14—H14B	109.6	O2—C24—O3	126.38 (16)
C13—C14—H14B	109.6	O2—C24—C19	116.49 (15)
H14A—C14—H14B	108.1	O3—C24—C19	117.13 (14)
C17—N4—C16	109.63 (13)
C7—C12—C11—C10	−0.8 (3)	N1—C2—N2—C13	−8.8 (2)
C12—C11—C10—C9	−0.2 (3)	N3—C2—N2—C13	174.62 (15)
C12—C11—C10—Cl1	179.37 (15)	C2—N2—C13—C14	163.72 (15)
C11—C10—C9—C8	0.8 (3)	C15—N2—C13—C14	−55.26 (19)
Cl1—C10—C9—C8	−178.71 (14)	N2—C13—C14—N4	56.92 (18)
C10—C9—C8—C7	−0.6 (3)	C13—C14—N4—C17	178.91 (14)
C11—C12—C7—C8	1.0 (3)	C13—C14—N4—C16	−59.02 (17)
C11—C12—C7—C6	−177.17 (17)	C17—N4—C16—C15	−176.41 (14)
C9—C8—C7—C12	−0.3 (3)	C14—N4—C16—C15	59.30 (17)
C9—C8—C7—C6	177.75 (17)	C2—N2—C15—C16	−164.89 (15)
C12—C7—C6—C5	167.17 (19)	C13—N2—C15—C16	55.39 (18)
C8—C7—C6—C5	−10.9 (3)	N4—C16—C15—N2	−57.32 (19)
C7—C6—C5—N1	−1.0 (3)	C16—N4—C17—C18	168.08 (15)
C7—C6—C5—C4	−170.62 (17)	C14—N4—C17—C18	−70.43 (19)
C6—C5—N1—C2	−168.27 (18)	N4—C17—C18—O1	−173.10 (14)
C4—C5—N1—C2	2.37 (19)	C19—C20—C21—C22	1.7 (3)
C5—N1—C2—N2	−178.77 (16)	C20—C21—C22—C23	0.3 (3)
C5—N1—C2—N3	−2.0 (2)	C21—C22—C23—N5	−1.5 (3)
N1—C2—N3—C4	0.8 (2)	C22—C23—N5—C19	0.7 (3)
N2—C2—N3—C4	177.68 (15)	C23—N5—C19—C20	1.4 (3)
C2—N3—C4—O4	178.92 (17)	C23—N5—C19—C24	−177.84 (16)
C2—N3—C4—C5	0.73 (17)	C21—C20—C19—N5	−2.6 (3)
C6—C5—C4—O4	−8.5 (3)	C21—C20—C19—C24	176.59 (16)
N1—C5—C4—O4	179.99 (17)	N5—C19—C24—O2	177.51 (15)
C6—C5—C4—N3	169.60 (16)	C20—C19—C24—O2	−1.8 (2)
N1—C5—C4—N3	−1.93 (18)	N5—C19—C24—O3	−2.0 (2)
N1—C2—N2—C15	−147.47 (17)	C20—C19—C24—O3	178.70 (16)
N3—C2—N2—C15	35.9 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13B···O4^i	0.99	2.64	3.287 (2)	123
C13—H13B···O3	0.99	2.64	3.302 (2)	124
C14—H14B···O4^ii	0.99	2.45	3.299 (2)	144
C16—H16A···O4^ii	0.99	2.52	3.359 (2)	142
C16—H16B···O2^iii	0.99	2.61	3.202 (2)	119
C15—H15A···O1^iv	0.99	2.37	3.091 (2)	129
C15—H15B···O3^v	0.99	2.49	3.422 (2)	157
C17—H17B···O4^ii	0.99	2.47	3.317 (2)	144
C18—H18A···O3	0.99	2.6	3.249 (2)	123
C22—H22···N5^vi	0.95	2.58	3.402 (2)	145
N3—H3···O3^v	0.94 (2)	1.86 (2)	2.796 (2)	173 (2)
N4—H4···N5	0.89 (2)	2.38 (2)	3.095 (2)	137 (2)
N4—H4···O3	0.89 (2)	1.96 (2)	2.747 (2)	147 (2)
O1—H1···O2^vii	0.92 (3)	1.80 (3)	2.704 (2)	166 (2)

Symmetry codes: (i) x, y−1, z; (ii) x, −y+1/2, z+1/2; (iii) x, −y−1/2, z+1/2; (iv) x, −y−1/2, z−1/2; (v) x, y+1, z; (vi) −x, y+1/2, −z+1/2; (vii) x, −y−3/2, 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)

Crystal data

C16H20ClN4O2^+·C8H6NO4^−	Z = 2
Mr = 515.95	F(000) = 540
Triclinic, P1	Dx = 1.395 Mg m^−3
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54184 Å
a = 7.8667 (4) Å	Cell parameters from 4966 reflections
b = 11.9015 (7) Å	θ = 3.3–71.8°
c = 14.4406 (9) Å	µ = 1.81 mm^−1
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) Å^3

Data collection

Rigaku SuperNova Dual Source diffractometer with an Atlas detector	4750 independent reflections
Radiation source: micro-focus sealed X-ray tube	3217 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.072
Detector resolution: 10.3756 pixels mm^-1	θmax = 71.8°, θmin = 3.3°
ω scans	h = −9→9
Absorption correction: gaussian (CrysAlis PRO; Rigaku OD, 2015)	k = −14→14
Tmin = 0.824, Tmax = 0.947	l = −17→17
17827 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.068	w = 1/[σ^2(Fo^2) + (0.1334P)^2 + 0.0797P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.223	(Δ/σ)max = 0.001
S = 1.03	Δρmax = 0.24 e Å^−3
4750 reflections	Δρmin = −0.40 e Å^−3
354 parameters	Extinction correction: SHELXL2013 (Sheldrick, 2015), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
2 restraints	Extinction coefficient: 0.0034 (10)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
C2	0.9074 (3)	1.1563 (2)	0.8711 (2)	0.0626 (6)
C4	1.1738 (4)	1.1112 (3)	0.8186 (2)	0.0702 (7)
C5	1.0437 (3)	1.0585 (2)	0.7838 (2)	0.0656 (7)
C6	1.0850 (4)	1.0010 (3)	0.7199 (2)	0.0696 (7)
H6	1.2017	0.9878	0.7048	0.084*
C7	0.9712 (4)	0.9568 (2)	0.6713 (2)	0.0662 (7)
C8	0.7925 (4)	0.9911 (3)	0.6676 (2)	0.0710 (7)
H8	0.742	1.045	0.6974	0.085*
C9	0.6915 (4)	0.9464 (3)	0.6208 (2)	0.0772 (8)
H9	0.5735	0.9713	0.6178	0.093*
C10	0.7647 (5)	0.8637 (3)	0.5775 (3)	0.0815 (9)
C11	0.9421 (5)	0.8314 (3)	0.5774 (2)	0.0811 (9)
H11	0.9922	0.7785	0.5466	0.097*
C12	1.0424 (4)	0.8781 (3)	0.6230 (2)	0.0741 (8)
H12	1.1611	0.857	0.622	0.089*
C13	0.6051 (3)	1.1853 (3)	0.9131 (3)	0.0732 (8)
H13A	0.6025	1.1132	0.8979	0.088*
H13B	0.5523	1.2567	0.8584	0.088*
C14	0.5053 (3)	1.1712 (3)	1.0105 (2)	0.0681 (7)
H14A	0.3861	1.1651	1.003	0.082*
H14B	0.5522	1.0958	1.0639	0.082*
C15	0.7990 (4)	1.3020 (3)	0.9521 (3)	0.0716 (8)
H15A	0.7567	1.3794	0.8992	0.086*
H15B	0.9192	1.3037	0.9613	0.086*
C16	0.6990 (3)	1.2885 (3)	1.0478 (2)	0.0691 (7)
H16A	0.7058	1.3593	1.0642	0.083*
H16B	0.749	1.2155	1.1022	0.083*
C17	0.4154 (4)	1.2688 (3)	1.1355 (2)	0.0777 (8)
H17A	0.4545	1.19	1.1879	0.093*
H17B	0.443	1.3327	1.1554	0.093*
C18	0.2232 (4)	1.2802 (3)	1.1300 (3)	0.0772 (8)
H18A	0.1955	1.2244	1.1011	0.093*
H18B	0.1733	1.2551	1.1978	0.093*
C19	0.0993 (4)	1.4825 (3)	0.6908 (2)	0.0650 (7)
C20	−0.0722 (4)	1.5135 (3)	0.7117 (3)	0.0760 (8)
H20	−0.1009	1.5639	0.7477	0.091*
C21	−0.2001 (4)	1.4717 (3)	0.6807 (3)	0.0769 (8)
H21	−0.3149	1.4938	0.6949	0.092*
C22	−0.1570 (4)	1.3968 (3)	0.6282 (2)	0.0681 (7)
C23	0.0123 (4)	1.3635 (3)	0.6064 (2)	0.0717 (7)
H23	0.0401	1.3129	0.5706	0.086*
C24	0.1395 (4)	1.4060 (3)	0.6384 (2)	0.0721 (7)
H24	0.2542	1.3831	0.6247	0.087*
C25	0.2391 (4)	1.5278 (3)	0.7276 (2)	0.0795 (9)
H25A	0.3411	1.5275	0.6849	0.095*
H25B	0.2018	1.6125	0.7196	0.095*
C26	0.2878 (3)	1.4542 (2)	0.8359 (2)	0.0608 (6)
N1	0.8816 (3)	1.0881 (2)	0.82195 (19)	0.0672 (6)
N2	0.7835 (3)	1.2002 (2)	0.9222 (2)	0.0724 (7)
N3	1.0772 (3)	1.1742 (2)	0.8716 (2)	0.0676 (6)
H3	1.113 (5)	1.232 (4)	0.888 (3)	0.101*
N4	0.5142 (3)	1.2783 (2)	1.03857 (17)	0.0606 (5)
HN4	0.467 (4)	1.351 (3)	0.985 (3)	0.091*
N5	−0.2917 (4)	1.3529 (3)	0.5927 (3)	0.0880 (8)
O1	0.1482 (3)	1.4005 (2)	1.0724 (2)	0.0936 (7)
H1	0.153 (6)	1.406 (5)	1.005 (4)	0.14*
O2	0.1998 (2)	1.37064 (18)	0.89135 (14)	0.0682 (5)
O3	0.4151 (3)	1.48002 (18)	0.86656 (15)	0.0730 (6)
O4	1.3296 (3)	1.1026 (2)	0.8054 (2)	0.0896 (7)
O5A	−0.243 (5)	1.327 (4)	0.525 (3)	0.121 (11)	0.22 (4)
O6A	−0.426 (3)	1.339 (2)	0.6425 (14)	0.077 (8)	0.22 (4)
O5B	−0.2577 (10)	1.2940 (12)	0.5389 (8)	0.094 (2)	0.78 (4)
O6B	−0.4396 (12)	1.384 (3)	0.6129 (19)	0.178 (5)	0.78 (4)
Cl1	0.63520 (16)	0.80286 (10)	0.52260 (9)	0.1174 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C2	0.0546 (13)	0.0636 (15)	0.0742 (17)	−0.0137 (11)	−0.0018 (12)	−0.0291 (13)
C4	0.0575 (15)	0.0651 (16)	0.086 (2)	−0.0105 (12)	−0.0053 (13)	−0.0257 (15)
C5	0.0573 (14)	0.0573 (14)	0.0815 (19)	−0.0095 (11)	−0.0005 (13)	−0.0255 (13)
C6	0.0609 (15)	0.0611 (15)	0.084 (2)	−0.0092 (12)	0.0060 (13)	−0.0264 (14)
C7	0.0714 (16)	0.0550 (14)	0.0698 (17)	−0.0135 (12)	0.0040 (13)	−0.0207 (13)
C8	0.0756 (17)	0.0631 (16)	0.0735 (18)	−0.0097 (13)	−0.0002 (14)	−0.0257 (14)
C9	0.0802 (19)	0.0676 (17)	0.078 (2)	−0.0080 (14)	−0.0118 (15)	−0.0201 (15)
C10	0.106 (2)	0.0659 (17)	0.0721 (19)	−0.0131 (16)	−0.0172 (17)	−0.0224 (15)
C11	0.104 (2)	0.0700 (18)	0.0718 (19)	−0.0047 (16)	−0.0038 (17)	−0.0318 (15)
C12	0.0824 (19)	0.0645 (16)	0.0711 (18)	−0.0083 (14)	0.0070 (15)	−0.0239 (14)
C13	0.0546 (14)	0.0827 (19)	0.102 (2)	−0.0168 (13)	−0.0014 (14)	−0.0542 (18)
C14	0.0569 (14)	0.0624 (15)	0.091 (2)	−0.0144 (11)	−0.0015 (13)	−0.0338 (14)
C15	0.0623 (15)	0.0812 (18)	0.091 (2)	−0.0264 (13)	0.0052 (14)	−0.0499 (16)
C16	0.0607 (15)	0.0759 (17)	0.0800 (19)	−0.0146 (13)	−0.0098 (13)	−0.0364 (15)
C17	0.085 (2)	0.085 (2)	0.0613 (17)	−0.0244 (16)	0.0035 (14)	−0.0229 (15)
C18	0.0805 (19)	0.0786 (19)	0.0745 (19)	−0.0179 (15)	0.0145 (15)	−0.0323 (16)
C19	0.0673 (15)	0.0641 (15)	0.0599 (15)	−0.0189 (12)	−0.0107 (12)	−0.0145 (12)
C20	0.0783 (19)	0.0770 (19)	0.082 (2)	−0.0122 (15)	−0.0031 (15)	−0.0398 (16)
C21	0.0594 (15)	0.086 (2)	0.092 (2)	−0.0087 (14)	−0.0016 (14)	−0.0420 (18)
C22	0.0587 (15)	0.0784 (18)	0.0706 (17)	−0.0147 (13)	−0.0093 (12)	−0.0286 (14)
C23	0.0671 (16)	0.0839 (19)	0.0711 (18)	−0.0111 (14)	−0.0064 (13)	−0.0358 (15)
C24	0.0554 (14)	0.0868 (19)	0.0765 (18)	−0.0104 (13)	−0.0073 (13)	−0.0323 (15)
C25	0.086 (2)	0.0771 (19)	0.0735 (19)	−0.0308 (16)	−0.0164 (15)	−0.0162 (15)
C26	0.0618 (14)	0.0585 (14)	0.0685 (16)	−0.0132 (11)	−0.0060 (12)	−0.0285 (12)
N1	0.0578 (12)	0.0684 (13)	0.0858 (16)	−0.0156 (10)	0.0016 (11)	−0.0387 (12)
N2	0.0569 (12)	0.0843 (16)	0.0986 (18)	−0.0222 (11)	0.0038 (12)	−0.0559 (14)
N3	0.0540 (12)	0.0706 (14)	0.0857 (16)	−0.0151 (10)	−0.0066 (11)	−0.0349 (12)
N4	0.0613 (12)	0.0617 (13)	0.0612 (13)	−0.0144 (10)	−0.0004 (10)	−0.0243 (10)
N5	0.0676 (16)	0.108 (2)	0.101 (2)	−0.0238 (15)	−0.0094 (16)	−0.0481 (18)
O1	0.1076 (18)	0.0878 (16)	0.0816 (15)	0.0015 (13)	−0.0005 (13)	−0.0341 (13)
O2	0.0682 (11)	0.0745 (12)	0.0656 (11)	−0.0260 (9)	−0.0036 (9)	−0.0246 (9)
O3	0.0737 (12)	0.0732 (12)	0.0765 (13)	−0.0263 (9)	−0.0162 (10)	−0.0248 (10)
O4	0.0538 (11)	0.1030 (17)	0.1184 (19)	−0.0120 (10)	−0.0037 (11)	−0.0485 (15)
O5A	0.18 (3)	0.14 (2)	0.081 (12)	−0.110 (19)	0.023 (12)	−0.066 (13)
O6A	0.062 (10)	0.101 (13)	0.076 (14)	−0.038 (7)	0.012 (6)	−0.036 (10)
O5B	0.089 (3)	0.106 (5)	0.109 (4)	−0.035 (3)	−0.015 (3)	−0.053 (4)
O6B	0.061 (3)	0.269 (13)	0.284 (12)	−0.026 (6)	−0.007 (6)	−0.190 (10)
Cl1	0.1404 (10)	0.1029 (7)	0.1250 (9)	−0.0017 (6)	−0.0550 (7)	−0.0556 (6)

Geometric parameters (Å, º)

C2—N1	1.316 (3)	C16—H16A	0.97
C2—N2	1.339 (4)	C16—H16B	0.97
C2—N3	1.385 (3)	C17—C18	1.504 (4)
C4—O4	1.218 (3)	C17—N4	1.514 (4)
C4—N3	1.380 (4)	C17—H17A	0.97
C4—C5	1.491 (4)	C17—H17B	0.97
C5—C6	1.342 (4)	C18—O1	1.408 (4)
C5—N1	1.396 (4)	C18—H18A	0.97
C6—C7	1.454 (4)	C18—H18B	0.97
C6—H6	0.93	C19—C20	1.384 (4)
C7—C8	1.402 (4)	C19—C24	1.384 (4)
C7—C12	1.402 (4)	C19—C25	1.512 (4)
C8—C9	1.369 (4)	C20—C21	1.365 (4)
C8—H8	0.93	C20—H20	0.93
C9—C10	1.394 (5)	C21—C22	1.371 (4)
C9—H9	0.93	C21—H21	0.93
C10—C11	1.391 (5)	C22—C23	1.377 (4)
C10—Cl1	1.733 (3)	C22—N5	1.460 (4)
C11—C12	1.369 (5)	C23—C24	1.373 (4)
C11—H11	0.93	C23—H23	0.93
C12—H12	0.93	C24—H24	0.93
C13—N2	1.464 (3)	C25—C26	1.511 (4)
C13—C14	1.512 (4)	C25—H25A	0.97
C13—H13A	0.97	C25—H25B	0.97
C13—H13B	0.97	C26—O3	1.253 (3)
C14—N4	1.494 (3)	C26—O2	1.263 (3)
C14—H14A	0.97	N3—H3	0.90 (4)
C14—H14B	0.97	N4—HN4	0.95 (4)
C15—N2	1.461 (3)	N5—O5A	1.15 (3)
C15—C16	1.494 (4)	N5—O6B	1.212 (10)
C15—H15A	0.97	N5—O6A	1.22 (2)
C15—H15B	0.97	N5—O5B	1.227 (10)
C16—N4	1.498 (3)	O1—H1	0.94 (5)
N1—C2—N2	123.9 (2)	C18—C17—H17B	108.5
N1—C2—N3	114.7 (3)	N4—C17—H17B	108.5
N2—C2—N3	121.3 (2)	H17A—C17—H17B	107.5
O4—C4—N3	126.4 (3)	O1—C18—C17	113.3 (3)
O4—C4—C5	129.8 (3)	O1—C18—H18A	108.9
N3—C4—C5	103.8 (2)	C17—C18—H18A	108.9
C6—C5—N1	128.8 (3)	O1—C18—H18B	108.9
C6—C5—C4	122.1 (3)	C17—C18—H18B	108.9
N1—C5—C4	108.9 (2)	H18A—C18—H18B	107.7
C5—C6—C7	128.5 (3)	C20—C19—C24	118.4 (3)
C5—C6—H6	115.8	C20—C19—C25	120.6 (3)
C7—C6—H6	115.8	C24—C19—C25	121.0 (3)
C8—C7—C12	117.6 (3)	C21—C20—C19	121.5 (3)
C8—C7—C6	123.4 (3)	C21—C20—H20	119.3
C12—C7—C6	118.9 (3)	C19—C20—H20	119.3
C9—C8—C7	120.9 (3)	C20—C21—C22	119.0 (3)
C9—C8—H8	119.5	C20—C21—H21	120.5
C7—C8—H8	119.5	C22—C21—H21	120.5
C8—C9—C10	120.3 (3)	C21—C22—C23	121.2 (3)
C8—C9—H9	119.9	C21—C22—N5	120.0 (3)
C10—C9—H9	119.9	C23—C22—N5	118.9 (3)
C11—C10—C9	119.8 (3)	C24—C23—C22	119.1 (3)
C11—C10—Cl1	120.1 (3)	C24—C23—H23	120.4
C9—C10—Cl1	120.1 (3)	C22—C23—H23	120.4
C12—C11—C10	119.5 (3)	C23—C24—C19	120.9 (3)
C12—C11—H11	120.3	C23—C24—H24	119.6
C10—C11—H11	120.3	C19—C24—H24	119.6
C11—C12—C7	121.8 (3)	C26—C25—C19	115.4 (2)
C11—C12—H12	119.1	C26—C25—H25A	108.4
C7—C12—H12	119.1	C19—C25—H25A	108.4
N2—C13—C14	109.9 (2)	C26—C25—H25B	108.4
N2—C13—H13A	109.7	C19—C25—H25B	108.4
C14—C13—H13A	109.7	H25A—C25—H25B	107.5
N2—C13—H13B	109.7	O3—C26—O2	122.9 (3)
C14—C13—H13B	109.7	O3—C26—C25	117.6 (2)
H13A—C13—H13B	108.2	O2—C26—C25	119.5 (2)
N4—C14—C13	110.9 (2)	C2—N1—C5	105.1 (2)
N4—C14—H14A	109.5	C2—N2—C15	123.4 (2)
C13—C14—H14A	109.5	C2—N2—C13	118.6 (2)
N4—C14—H14B	109.5	C15—N2—C13	113.3 (2)
C13—C14—H14B	109.5	C4—N3—C2	107.4 (2)
H14A—C14—H14B	108	C4—N3—H3	125 (2)
N2—C15—C16	110.8 (2)	C2—N3—H3	126 (2)
N2—C15—H15A	109.5	C14—N4—C16	109.0 (2)
C16—C15—H15A	109.5	C14—N4—C17	113.0 (2)
N2—C15—H15B	109.5	C16—N4—C17	109.8 (2)
C16—C15—H15B	109.5	C14—N4—HN4	108 (2)
H15A—C15—H15B	108.1	C16—N4—HN4	108 (2)
C15—C16—N4	111.2 (2)	C17—N4—HN4	109 (2)
C15—C16—H16A	109.4	O5A—N5—O6A	131 (2)
N4—C16—H16A	109.4	O6B—N5—O5B	121.0 (7)
C15—C16—H16B	109.4	O5A—N5—C22	111.1 (18)
N4—C16—H16B	109.4	O6B—N5—C22	117.5 (6)
H16A—C16—H16B	108	O6A—N5—C22	117.2 (11)
C18—C17—N4	115.0 (3)	O5B—N5—C22	121.4 (5)
C18—C17—H17A	108.5	C18—O1—H1	106 (3)
N4—C17—H17A	108.5
O4—C4—C5—C6	−7.5 (5)	C19—C25—C26—O3	172.6 (3)
N3—C4—C5—C6	172.7 (3)	C19—C25—C26—O2	−7.7 (4)
O4—C4—C5—N1	176.9 (3)	N2—C2—N1—C5	−177.5 (3)
N3—C4—C5—N1	−2.9 (3)	N3—C2—N1—C5	−1.3 (3)
N1—C5—C6—C7	1.7 (5)	C6—C5—N1—C2	−172.7 (3)
C4—C5—C6—C7	−172.9 (3)	C4—C5—N1—C2	2.5 (3)
C5—C6—C7—C8	14.1 (5)	N1—C2—N2—C15	−162.1 (3)
C5—C6—C7—C12	−167.6 (3)	N3—C2—N2—C15	21.9 (5)
C12—C7—C8—C9	1.7 (4)	N1—C2—N2—C13	−8.1 (5)
C6—C7—C8—C9	−180.0 (3)	N3—C2—N2—C13	176.0 (3)
C7—C8—C9—C10	1.3 (5)	C16—C15—N2—C2	−149.5 (3)
C8—C9—C10—C11	−3.3 (5)	C16—C15—N2—C13	55.3 (4)
C8—C9—C10—Cl1	177.5 (2)	C14—C13—N2—C2	148.2 (3)
C9—C10—C11—C12	2.3 (5)	C14—C13—N2—C15	−55.3 (3)
Cl1—C10—C11—C12	−178.6 (2)	O4—C4—N3—C2	−177.8 (3)
C10—C11—C12—C7	0.8 (5)	C5—C4—N3—C2	2.0 (3)
C8—C7—C12—C11	−2.8 (4)	N1—C2—N3—C4	−0.5 (4)
C6—C7—C12—C11	178.8 (3)	N2—C2—N3—C4	175.8 (3)
N2—C13—C14—N4	56.6 (3)	C13—C14—N4—C16	−57.9 (3)
N2—C15—C16—N4	−55.9 (3)	C13—C14—N4—C17	179.7 (2)
N4—C17—C18—O1	−71.1 (4)	C15—C16—N4—C14	57.5 (3)
C24—C19—C20—C21	−0.9 (5)	C15—C16—N4—C17	−178.2 (2)
C25—C19—C20—C21	−178.8 (3)	C18—C17—N4—C14	−68.3 (3)
C19—C20—C21—C22	0.4 (5)	C18—C17—N4—C16	169.8 (3)
C20—C21—C22—C23	−0.1 (5)	C21—C22—N5—O5A	156 (2)
C20—C21—C22—N5	−178.9 (3)	C23—C22—N5—O5A	−22 (2)
C21—C22—C23—C24	0.2 (5)	C21—C22—N5—O6B	−1.1 (17)
N5—C22—C23—C24	179.1 (3)	C23—C22—N5—O6B	−180.0 (16)
C22—C23—C24—C19	−0.7 (5)	C21—C22—N5—O6A	−30.0 (13)
C20—C19—C24—C23	1.0 (4)	C23—C22—N5—O6A	151.2 (13)
C25—C19—C24—C23	179.0 (3)	C21—C22—N5—O5B	174.1 (8)
C20—C19—C25—C26	81.5 (4)	C23—C22—N5—O5B	−4.7 (9)
C24—C19—C25—C26	−96.4 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···O5A^i	0.93	2.54	3.41 (4)	154
C11—H11···O5B^i	0.93	2.55	3.37 (1)	148
C13—H13A···O4^ii	0.97	2.67	3.242 (4)	118
C14—H14A···O2	0.97	2.64	3.186 (4)	116
C14—H14B···O4^iii	0.97	2.48	3.446 (4)	177
C15—H15B···O2^iv	0.97	2.46	3.334 (3)	150
C16—H16A···O3^v	0.97	2.52	3.416 (4)	153
C17—H17B···O3^v	0.97	2.54	3.441 (4)	155
C20—H20···O1^vi	0.93	2.78	3.624 (4)	152
C24—H24···O6A^iv	0.93	2.51	3.39 (3)	159
C24—H24···O6B^iv	0.93	2.40	3.282 (9)	158
C25—H25A···O6B^iv	0.97	2.68	3.505 (12)	143
N3—H3···O2^iv	0.90 (4)	1.89 (4)	2.781 (3)	168 (4)
N4—HN4···O2	0.95 (4)	2.53 (4)	3.177 (3)	125 (3)
N4—HN4···O3	0.95 (4)	1.82 (4)	2.761 (3)	168 (3)
O1—H1···O2	0.94 (5)	1.85 (5)	2.762 (3)	163 (5)

Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) x−1, 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.