2,6-Bis(1H-benzimidazol-2-yl)pyridine butyric acid monosolvate dihydrate.

In the title compound, C(19)H(13)N(5)·C(4)H(8)O(2)·2H(2)O, the mol-ecular skeleton of the 2,6-bis-(benzimidazol-2-yl)pyridine (bbip) mol-ecule is essentially planar (r.m.s. deviation = 0.023 Å). An extensive three-dimensional network of inter-molecular N-H⋯O, O-H⋯O and O-H⋯N hydrogen bonds consolidates the crystal packing, which also exhibits π-π inter-actions between the five- and six-membered rings from neighbouring bbip mol-ecules.

Related literature

For background to supra­molecular inter­actions, see: Dale et al. (2004 ▶); Braga et al. (2005 ▶); Ring et al. (2006 ▶). For related structures, see: Freire et al. (2003 ▶); Xiao et al. (2010 ▶).

Experimental

Crystal data

C19H13N5·C4H8O2·2H2O

M = 435.48

Triclinic,

a = 9.3950 (19) Å

b = 9.5611 (19) Å

c = 13.805 (3) Å

α = 103.27 (2)°

β = 99.91 (3)°

γ = 104.76 (3)°

V = 1131.5 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 295 K

0.20 × 0.18 × 0.15 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.982, T max = 0.987

8683 measured reflections

3981 independent reflections

3195 reflections with I > 2σ(I)

R int = 0.019

3 standard reflections every 100 reflections intensity decay: none

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.144

S = 1.10

3981 reflections

318 parameters

6 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.22 e Å−3

Δρmin = −0.25 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ▶); cell refinement: CAD-4 Software; data reduction: NRCVAX (Gabe et al., 1989 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812021915/cv5296sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812021915/cv5296Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812021915/cv5296Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C19H13N5·C4H8O2·2H2O	Z = 2
Mr = 435.48	F(000) = 460
Triclinic, P1	Dx = 1.278 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.3950 (19) Å	Cell parameters from 25 reflections
b = 9.5611 (19) Å	θ = 4–14°
c = 13.805 (3) Å	µ = 0.09 mm−1
α = 103.27 (2)°	T = 295 K
β = 99.91 (3)°	Block, colourless
γ = 104.76 (3)°	0.20 × 0.18 × 0.15 mm
V = 1131.5 (4) Å3

Enraf–Nonius CAD-4 diffractometer	3195 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.019
Graphite monochromator	θmax = 25.0°, θmin = 3.1°
ω scans	h = −11→11
Absorption correction: ψ scan (North et al., 1968)	k = −11→10
Tmin = 0.982, Tmax = 0.987	l = −16→16
8683 measured reflections	3 standard reflections every 100 reflections
3981 independent reflections	intensity decay: none

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.045	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.144	w = 1/[σ2(Fo2) + (0.0925P)2 + 0.059P] where P = (Fo2 + 2Fc2)/3
S = 1.10	(Δ/σ)max < 0.001
3981 reflections	Δρmax = 0.22 e Å−3
318 parameters	Δρmin = −0.25 e Å−3
6 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.007 (3)

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

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
N1	0.12979 (14)	0.51453 (15)	−0.18153 (10)	0.0466 (3)
N2	−0.05854 (14)	0.30191 (14)	−0.26517 (10)	0.0482 (3)
N3	−0.04327 (13)	0.62903 (14)	−0.06414 (9)	0.0407 (3)
N4	−0.10826 (15)	0.91520 (15)	0.12949 (10)	0.0473 (3)
N5	0.10055 (14)	0.91107 (14)	0.07405 (10)	0.0423 (3)
C1	0.06996 (18)	0.29713 (18)	−0.30066 (12)	0.0491 (4)
C2	0.0931 (2)	0.1845 (2)	−0.37465 (15)	0.0685 (5)
H2B	0.0151	0.0957	−0.4100	0.082*
C3	0.2354 (2)	0.2091 (2)	−0.39367 (18)	0.0796 (6)
H3B	0.2528	0.1363	−0.4437	0.095*
C4	0.3535 (2)	0.3401 (3)	−0.33982 (19)	0.0801 (7)
H4B	0.4485	0.3517	−0.3538	0.096*
C5	0.3335 (2)	0.4530 (2)	−0.26625 (15)	0.0652 (5)
H5B	0.4126	0.5406	−0.2303	0.078*
C6	0.18948 (18)	0.42972 (18)	−0.24846 (12)	0.0479 (4)
C7	−0.01687 (16)	0.43359 (16)	−0.19367 (11)	0.0424 (4)
C8	−0.11129 (17)	0.49146 (16)	−0.13058 (11)	0.0422 (4)
C9	−0.25971 (18)	0.40738 (18)	−0.13928 (13)	0.0526 (4)
H9A	−0.3028	0.3116	−0.1857	0.063*
C10	−0.34091 (19)	0.46967 (19)	−0.07748 (14)	0.0575 (5)
H10A	−0.4405	0.4162	−0.0816	0.069*
C11	−0.27421 (18)	0.61135 (18)	−0.00955 (13)	0.0511 (4)
H11A	−0.3277	0.6555	0.0326	0.061*
C12	−0.12534 (16)	0.68670 (16)	−0.00542 (11)	0.0408 (4)
C13	−0.04638 (16)	0.83768 (16)	0.06640 (11)	0.0409 (3)
C14	0.00703 (18)	1.04751 (17)	0.18249 (11)	0.0464 (4)
C15	0.0069 (2)	1.1702 (2)	0.25982 (14)	0.0621 (5)
H15A	−0.0794	1.1716	0.2839	0.075*
C16	0.1385 (2)	1.2887 (2)	0.29928 (15)	0.0689 (5)
H16A	0.1412	1.3716	0.3511	0.083*
C17	0.2687 (2)	1.2877 (2)	0.26338 (14)	0.0633 (5)
H17A	0.3556	1.3705	0.2918	0.076*
C18	0.27226 (19)	1.16824 (18)	0.18751 (13)	0.0536 (4)
H18A	0.3589	1.1682	0.1636	0.064*
C19	0.13926 (17)	1.04728 (17)	0.14830 (11)	0.0438 (4)
O1	−0.44196 (15)	0.06635 (14)	−0.27630 (11)	0.0743 (4)
O2	−0.28356 (15)	0.04486 (15)	−0.37563 (10)	0.0657 (4)
C20	−0.7674 (3)	−0.3547 (3)	−0.4697 (2)	0.1110 (10)
H20A	−0.8595	−0.3850	−0.4481	0.167*
H20B	−0.7183	−0.4317	−0.4725	0.167*
H20C	−0.7909	−0.3404	−0.5366	0.167*
C21	−0.6624 (2)	−0.2079 (2)	−0.39388 (18)	0.0824 (7)
H21A	−0.7139	−0.1315	−0.3902	0.099*
H21B	−0.6411	−0.2228	−0.3263	0.099*
C22	−0.5148 (2)	−0.1512 (2)	−0.42169 (14)	0.0611 (5)
H22A	−0.4618	−0.2261	−0.4227	0.073*
H22B	−0.5366	−0.1408	−0.4905	0.073*
C23	−0.41213 (18)	−0.00337 (18)	−0.35032 (13)	0.0500 (4)
O1W	−0.40511 (15)	0.92334 (16)	0.11934 (11)	0.0647 (4)
O2W	0.32779 (16)	0.81969 (16)	−0.04472 (12)	0.0690 (4)
H2	0.1745 (19)	0.6070 (13)	−0.1365 (11)	0.057 (5)*
H1	0.156 (2)	0.873 (2)	0.0390 (14)	0.056 (5)*
H2W1	−0.3168 (14)	0.920 (3)	0.1236 (19)	0.100 (8)*
H2W2	0.350 (3)	0.885 (2)	−0.0747 (19)	0.116 (10)*
H1W2	0.407 (2)	0.839 (3)	−0.0027 (17)	0.129 (12)*
H1W1	−0.435 (3)	0.928 (3)	0.1717 (13)	0.106 (9)*
H3	−0.228 (2)	0.1309 (16)	−0.3376 (16)	0.096 (8)*

	U11	U22	U33	U12	U13	U23
N1	0.0350 (7)	0.0439 (7)	0.0510 (7)	0.0049 (5)	0.0084 (6)	0.0045 (6)
N2	0.0399 (7)	0.0449 (7)	0.0514 (7)	0.0072 (6)	0.0116 (6)	0.0037 (6)
N3	0.0329 (6)	0.0430 (7)	0.0420 (6)	0.0082 (5)	0.0075 (5)	0.0094 (5)
N4	0.0398 (7)	0.0497 (7)	0.0466 (7)	0.0087 (6)	0.0125 (6)	0.0070 (6)
N5	0.0336 (7)	0.0437 (7)	0.0456 (7)	0.0076 (5)	0.0109 (5)	0.0089 (6)
C1	0.0409 (9)	0.0491 (9)	0.0513 (9)	0.0088 (7)	0.0121 (7)	0.0078 (7)
C2	0.0587 (11)	0.0579 (11)	0.0726 (12)	0.0080 (9)	0.0231 (9)	−0.0063 (9)
C3	0.0684 (13)	0.0722 (13)	0.0897 (14)	0.0193 (10)	0.0379 (11)	−0.0039 (11)
C4	0.0530 (12)	0.0789 (13)	0.1034 (16)	0.0164 (10)	0.0377 (11)	0.0069 (12)
C5	0.0414 (9)	0.0656 (11)	0.0781 (12)	0.0069 (8)	0.0204 (9)	0.0071 (10)
C6	0.0401 (8)	0.0490 (8)	0.0510 (9)	0.0116 (7)	0.0120 (7)	0.0094 (7)
C7	0.0351 (8)	0.0431 (8)	0.0445 (8)	0.0082 (6)	0.0065 (6)	0.0106 (6)
C8	0.0364 (8)	0.0405 (7)	0.0456 (8)	0.0082 (6)	0.0073 (6)	0.0104 (6)
C9	0.0399 (9)	0.0417 (8)	0.0638 (10)	0.0011 (7)	0.0123 (8)	0.0048 (7)
C10	0.0368 (8)	0.0498 (9)	0.0759 (12)	−0.0013 (7)	0.0209 (8)	0.0102 (8)
C11	0.0403 (9)	0.0485 (9)	0.0615 (10)	0.0072 (7)	0.0215 (7)	0.0104 (7)
C12	0.0337 (8)	0.0426 (8)	0.0441 (8)	0.0075 (6)	0.0092 (6)	0.0138 (6)
C13	0.0340 (8)	0.0431 (8)	0.0415 (8)	0.0064 (6)	0.0079 (6)	0.0114 (6)
C14	0.0438 (9)	0.0447 (8)	0.0432 (8)	0.0073 (7)	0.0080 (7)	0.0076 (7)
C15	0.0603 (11)	0.0585 (10)	0.0579 (10)	0.0134 (9)	0.0179 (8)	0.0011 (8)
C16	0.0769 (14)	0.0522 (10)	0.0569 (10)	0.0108 (9)	0.0056 (9)	−0.0058 (8)
C17	0.0569 (11)	0.0499 (9)	0.0618 (11)	−0.0010 (8)	−0.0030 (9)	0.0077 (8)
C18	0.0413 (9)	0.0513 (9)	0.0569 (10)	0.0023 (7)	0.0027 (7)	0.0138 (8)
C19	0.0387 (8)	0.0453 (8)	0.0416 (8)	0.0073 (6)	0.0041 (6)	0.0118 (7)
O1	0.0559 (8)	0.0539 (7)	0.0927 (10)	0.0011 (6)	0.0302 (7)	−0.0089 (7)
O2	0.0543 (8)	0.0667 (8)	0.0587 (7)	0.0007 (6)	0.0171 (6)	0.0021 (6)
C20	0.103 (2)	0.0735 (15)	0.1010 (18)	−0.0274 (14)	−0.0127 (15)	0.0078 (13)
C21	0.0645 (13)	0.0620 (12)	0.0910 (15)	−0.0090 (10)	0.0110 (11)	0.0033 (11)
C22	0.0641 (12)	0.0533 (9)	0.0529 (9)	0.0096 (9)	0.0011 (8)	0.0096 (8)
C23	0.0453 (9)	0.0477 (9)	0.0533 (9)	0.0119 (7)	0.0087 (7)	0.0123 (7)
O1W	0.0420 (7)	0.0799 (9)	0.0668 (8)	0.0146 (6)	0.0135 (6)	0.0150 (7)
O2W	0.0487 (8)	0.0607 (8)	0.0793 (9)	−0.0024 (6)	0.0019 (7)	0.0172 (7)

N1—C7	1.358 (2)	C11—H11A	0.9300
N1—C6	1.375 (2)	C12—C13	1.470 (2)
N1—H2	0.90 (2)	C14—C15	1.393 (2)
N2—C7	1.3259 (19)	C14—C19	1.403 (2)
N2—C1	1.386 (2)	C15—C16	1.371 (3)
N3—C12	1.3350 (19)	C15—H15A	0.9300
N3—C8	1.3401 (19)	C16—C17	1.398 (3)
N4—C13	1.3203 (19)	C16—H16A	0.9300
N4—C14	1.383 (2)	C17—C18	1.373 (3)
N5—C13	1.3533 (19)	C17—H17A	0.9300
N5—C19	1.377 (2)	C18—C19	1.391 (2)
N5—H1	0.86 (2)	C18—H18A	0.9300
C1—C2	1.393 (2)	O1—C23	1.203 (2)
C1—C6	1.401 (2)	O2—C23	1.315 (2)
C2—C3	1.379 (3)	O2—H3	0.85 (2)
C2—H2B	0.9300	C20—C21	1.518 (3)
C3—C4	1.391 (3)	C20—H20A	0.9600
C3—H3B	0.9300	C20—H20B	0.9600
C4—C5	1.378 (3)	C20—H20C	0.9600
C4—H4B	0.9300	C21—C22	1.504 (3)
C5—C6	1.388 (2)	C21—H21A	0.9700
C5—H5B	0.9300	C21—H21B	0.9700
C7—C8	1.465 (2)	C22—C23	1.496 (2)
C8—C9	1.390 (2)	C22—H22A	0.9700
C9—C10	1.374 (2)	C22—H22B	0.9700
C9—H9A	0.9300	O1W—H2W1	0.83 (2)
C10—C11	1.374 (2)	O1W—H1W1	0.82 (2)
C10—H10A	0.9300	O2W—H2W2	0.82 (2)
C11—C12	1.385 (2)	O2W—H1W2	0.81 (2)
C7—N1—C6	107.54 (13)	N4—C13—N5	113.13 (13)
C7—N1—H2	123.1 (12)	N4—C13—C12	124.76 (13)
C6—N1—H2	129.3 (12)	N5—C13—C12	122.12 (13)
C7—N2—C1	104.86 (13)	N4—C14—C15	129.84 (16)
C12—N3—C8	117.15 (13)	N4—C14—C19	110.09 (13)
C13—N4—C14	104.64 (13)	C15—C14—C19	120.07 (16)
C13—N5—C19	107.30 (13)	C16—C15—C14	117.73 (18)
C13—N5—H1	123.4 (13)	C16—C15—H15A	121.1
C19—N5—H1	129.3 (13)	C14—C15—H15A	121.1
N2—C1—C2	130.11 (16)	C15—C16—C17	121.52 (17)
N2—C1—C6	109.96 (14)	C15—C16—H16A	119.2
C2—C1—C6	119.92 (16)	C17—C16—H16A	119.2
C3—C2—C1	117.73 (18)	C18—C17—C16	122.03 (17)
C3—C2—H2B	121.1	C18—C17—H17A	119.0
C1—C2—H2B	121.1	C16—C17—H17A	119.0
C2—C3—C4	121.61 (18)	C17—C18—C19	116.43 (17)
C2—C3—H3B	119.2	C17—C18—H18A	121.8
C4—C3—H3B	119.2	C19—C18—H18A	121.8
C5—C4—C3	121.71 (18)	N5—C19—C18	132.95 (15)
C5—C4—H4B	119.1	N5—C19—C14	104.84 (14)
C3—C4—H4B	119.1	C18—C19—C14	122.20 (15)
C4—C5—C6	116.72 (18)	C23—O2—H3	113.9 (17)
C4—C5—H5B	121.6	C21—C20—H20A	109.5
C6—C5—H5B	121.6	C21—C20—H20B	109.5
N1—C6—C5	132.63 (16)	H20A—C20—H20B	109.5
N1—C6—C1	105.07 (14)	C21—C20—H20C	109.5
C5—C6—C1	122.27 (16)	H20A—C20—H20C	109.5
N2—C7—N1	112.57 (13)	H20B—C20—H20C	109.5
N2—C7—C8	126.42 (14)	C22—C21—C20	113.3 (2)
N1—C7—C8	121.00 (13)	C22—C21—H21A	108.9
N3—C8—C9	123.26 (14)	C20—C21—H21A	108.9
N3—C8—C7	115.06 (13)	C22—C21—H21B	108.9
C9—C8—C7	121.67 (14)	C20—C21—H21B	108.9
C10—C9—C8	118.15 (15)	H21A—C21—H21B	107.7
C10—C9—H9A	120.9	C23—C22—C21	114.24 (16)
C8—C9—H9A	120.9	C23—C22—H22A	108.7
C9—C10—C11	119.67 (15)	C21—C22—H22A	108.7
C9—C10—H10A	120.2	C23—C22—H22B	108.7
C11—C10—H10A	120.2	C21—C22—H22B	108.7
C10—C11—C12	118.33 (15)	H22A—C22—H22B	107.6
C10—C11—H11A	120.8	O1—C23—O2	122.25 (16)
C12—C11—H11A	120.8	O1—C23—C22	124.19 (16)
N3—C12—C11	123.43 (14)	O2—C23—C22	113.56 (15)
N3—C12—C13	115.37 (13)	H2W1—O1W—H1W1	117 (3)
C11—C12—C13	121.19 (14)	H2W2—O2W—H1W2	102 (3)
C7—N2—C1—C2	178.8 (2)	C8—N3—C12—C13	179.95 (13)
C7—N2—C1—C6	−0.07 (19)	C10—C11—C12—N3	0.1 (3)
N2—C1—C2—C3	−178.9 (2)	C10—C11—C12—C13	−179.18 (15)
C6—C1—C2—C3	−0.1 (3)	C14—N4—C13—N5	−0.62 (17)
C1—C2—C3—C4	1.3 (4)	C14—N4—C13—C12	179.13 (14)
C2—C3—C4—C5	−1.3 (4)	C19—N5—C13—N4	0.37 (18)
C3—C4—C5—C6	0.0 (4)	C19—N5—C13—C12	−179.38 (13)
C7—N1—C6—C5	−177.18 (19)	N3—C12—C13—N4	178.66 (14)
C7—N1—C6—C1	0.76 (18)	C11—C12—C13—N4	−2.0 (2)
C4—C5—C6—N1	178.9 (2)	N3—C12—C13—N5	−1.6 (2)
C4—C5—C6—C1	1.2 (3)	C11—C12—C13—N5	177.75 (14)
N2—C1—C6—N1	−0.43 (19)	C13—N4—C14—C15	−178.98 (18)
C2—C1—C6—N1	−179.43 (17)	C13—N4—C14—C19	0.63 (17)
N2—C1—C6—C5	177.78 (16)	N4—C14—C15—C16	−179.71 (17)
C2—C1—C6—C5	−1.2 (3)	C19—C14—C15—C16	0.7 (3)
C1—N2—C7—N1	0.58 (18)	C14—C15—C16—C17	0.2 (3)
C1—N2—C7—C8	−178.33 (15)	C15—C16—C17—C18	−0.4 (3)
C6—N1—C7—N2	−0.87 (19)	C16—C17—C18—C19	−0.3 (3)
C6—N1—C7—C8	178.11 (14)	C13—N5—C19—C18	−179.13 (17)
C12—N3—C8—C9	−1.1 (2)	C13—N5—C19—C14	0.05 (17)
C12—N3—C8—C7	179.62 (13)	C17—C18—C19—N5	−179.70 (17)
N2—C7—C8—N3	−179.30 (14)	C17—C18—C19—C14	1.2 (2)
N1—C7—C8—N3	1.9 (2)	N4—C14—C19—N5	−0.42 (17)
N2—C7—C8—C9	1.4 (3)	C15—C14—C19—N5	179.24 (15)
N1—C7—C8—C9	−177.42 (15)	N4—C14—C19—C18	178.87 (14)
N3—C8—C9—C10	0.9 (3)	C15—C14—C19—C18	−1.5 (3)
C7—C8—C9—C10	−179.91 (15)	C20—C21—C22—C23	177.6 (2)
C8—C9—C10—C11	−0.1 (3)	C21—C22—C23—O1	0.2 (3)
C9—C10—C11—C12	−0.4 (3)	C21—C22—C23—O2	−179.94 (17)
C8—N3—C12—C11	0.6 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H2···O2W	0.90 (2)	2.12 (1)	3.006 (2)	166 (2)
N5—H1···O2W	0.86 (2)	2.234 (19)	3.083 (2)	169.1 (17)
O1W—H2W1···N4	0.83 (2)	1.96 (1)	2.7901 (19)	178 (3)
O2W—H2W2···O1Wi	0.82 (2)	2.04 (1)	2.852 (2)	168 (3)
O2W—H1W2···O1Wii	0.81 (2)	2.06 (1)	2.856 (2)	168 (3)
O1W—H1W1···O1iii	0.82 (2)	2.00 (1)	2.795 (2)	166 (3)
O2—H3···N2	0.85 (2)	1.89 (1)	2.712 (2)	164 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H2⋯O2W	0.90 (2)	2.12 (1)	3.006 (2)	166 (2)
N5—H1⋯O2W	0.86 (2)	2.234 (19)	3.083 (2)	169.1 (17)
O1W—H2W1⋯N4	0.83 (2)	1.96 (1)	2.7901 (19)	178 (3)
O2W—H2W2⋯O1Wi	0.82 (2)	2.04 (1)	2.852 (2)	168 (3)
O2W—H1W2⋯O1Wii	0.81 (2)	2.06 (1)	2.856 (2)	168 (3)
O1W—H1W1⋯O1iii	0.82 (2)	2.00 (1)	2.795 (2)	166 (3)
O2—H3⋯N2	0.85 (2)	1.89 (1)	2.712 (2)	164 (2)

Symmetry codes: (i) ; (ii) ; (iii) .