2-Eth-oxy-6-{[1-(3-eth-oxy-2-hy-droxy-benz-yl)-1H-benzimidazol-2-yl]meth-yl}phenol nitro-methane monosolvate.

In the title solvate, C(24)H(24)N(2)O(4)·CH(3)NO(2), the benzene ring of the 2-eth-oxy-6-methyl-phenol substituent is approximately perpendicular to the nearly planar benzimidazole ring [maximum deviation = 0.021 (2) Å], making a dihedral angle of 84.32 (7)°. The benzene ring of the 2-eth-oxy-phenol group is somewhat inclined to the benzimidazole ring plane by 28.03 (5)°. The dihedral angle between the benzene rings is 82.20 (9)°. The compound reveals strong intra-molecular O-H⋯N and O-H⋯O hydrogen bonds, forming six- and five-membered rings, respectively. In the crystal, mol-ecules are connected by bifurcated O-H⋯(O,O) hydrogen bonds, forming chains along the b axis.

Related literature

For the crystal structure of the meth­oxy derivative of the title compound, see: Al-Douh et al. (2009 ▶). For the crystal structure of the title compound as an acetonitrile monosolvate, see: Ha (2012 ▶).

Experimental

Crystal data

C24H24N2O4·CH3NO2

M = 465.50

Monoclinic,

a = 7.5151 (7) Å

b = 19.6463 (17) Å

c = 16.2578 (15) Å

β = 99.898 (2)°

V = 2364.6 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 273 K

0.36 × 0.20 × 0.13 mm

Data collection

Bruker SMART 1000 CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.856, T max = 1.000

17462 measured reflections

5846 independent reflections

2523 reflections with I > 2σ(I)

R int = 0.090

Refinement

R[F 2 > 2σ(F 2)] = 0.064

wR(F 2) = 0.157

S = 0.95

5846 reflections

318 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.29 e Å−3

Δρmin = −0.22 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812023665/tk5103sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812023665/tk5103Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812023665/tk5103Isup3.cml

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

C24H24N2O4·CH3NO2	F(000) = 984
Mr = 465.50	Dx = 1.308 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2443 reflections
a = 7.5151 (7) Å	θ = 2.8–22.7°
b = 19.6463 (17) Å	µ = 0.09 mm−1
c = 16.2578 (15) Å	T = 273 K
β = 99.898 (2)°	Block, orange
V = 2364.6 (4) Å3	0.36 × 0.20 × 0.13 mm
Z = 4

Bruker SMART 1000 CCD diffractometer	5846 independent reflections
Radiation source: fine-focus sealed tube	2523 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.090
φ and ω scans	θmax = 28.3°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −9→10
Tmin = 0.856, Tmax = 1.000	k = −26→23
17462 measured reflections	l = −21→21

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.064	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.157	H atoms treated by a mixture of independent and constrained refinement
S = 0.95	w = 1/[σ2(Fo2) + (0.0503P)2] where P = (Fo2 + 2Fc2)/3
5846 reflections	(Δ/σ)max < 0.001
318 parameters	Δρmax = 0.29 e Å−3
0 restraints	Δρmin = −0.22 e Å−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
O1	0.1517 (3)	−0.00824 (8)	0.25918 (12)	0.0364 (5)
H1O	0.166 (5)	0.0034 (17)	0.206 (2)	0.105 (14)*
O2	0.1909 (3)	−0.02200 (9)	0.41939 (11)	0.0421 (5)
O3	−0.0023 (2)	0.36913 (9)	0.19378 (11)	0.0367 (5)
H3O	−0.032 (4)	0.4180 (15)	0.1965 (19)	0.076 (10)*
O4	0.2353 (2)	0.47405 (8)	0.21047 (12)	0.0399 (5)
N1	0.2058 (3)	0.06287 (10)	0.13119 (14)	0.0362 (6)
N2	0.1347 (3)	0.17347 (10)	0.13095 (13)	0.0329 (6)
C1	0.1707 (4)	0.08554 (13)	0.04930 (17)	0.0352 (7)
C2	0.1729 (4)	0.05148 (14)	−0.02530 (18)	0.0424 (8)
H2	0.2012	0.0054	−0.0258	0.051*
C3	0.1320 (4)	0.08766 (15)	−0.09819 (18)	0.0475 (8)
H3	0.1329	0.0657	−0.1488	0.057*
C4	0.0889 (4)	0.15692 (15)	−0.09826 (19)	0.0494 (8)
H4	0.0629	0.1801	−0.1488	0.059*
C5	0.0841 (4)	0.19139 (14)	−0.02510 (19)	0.0453 (8)
H5	0.0545	0.2373	−0.0249	0.054*
C6	0.1256 (4)	0.15445 (13)	0.04832 (17)	0.0345 (7)
C7	0.1872 (3)	0.11683 (12)	0.17827 (16)	0.0312 (6)
C8	0.2174 (3)	0.11250 (12)	0.26941 (16)	0.0311 (6)
C9	0.1955 (3)	0.04905 (12)	0.30544 (16)	0.0298 (6)
C10	0.2224 (4)	0.04219 (13)	0.39271 (17)	0.0336 (7)
C11	0.2786 (4)	0.09698 (14)	0.44263 (18)	0.0403 (7)
H11	0.2974	0.0924	0.5004	0.048*
C12	0.3074 (4)	0.15947 (14)	0.40681 (18)	0.0433 (8)
H12	0.3477	0.1963	0.4409	0.052*
C13	0.2772 (4)	0.16734 (13)	0.32187 (18)	0.0396 (7)
H13	0.2965	0.2095	0.2989	0.048*
C14	0.2320 (4)	−0.03579 (14)	0.50701 (17)	0.0444 (8)
H14A	0.1562	−0.0085	0.5368	0.053*
H14B	0.3574	−0.0251	0.5285	0.053*
C15	0.1970 (4)	−0.11004 (14)	0.51828 (18)	0.0537 (9)
H15A	0.0730	−0.1201	0.4961	0.080*
H15B	0.2216	−0.1211	0.5766	0.080*
H15C	0.2741	−0.1365	0.4893	0.080*
C16	0.0750 (4)	0.23959 (12)	0.15603 (17)	0.0355 (7)
H16A	0.0374	0.2351	0.2099	0.043*
H16B	−0.0293	0.2539	0.1161	0.043*
C17	0.2187 (4)	0.29402 (12)	0.16189 (16)	0.0323 (7)
C18	0.1706 (4)	0.35914 (12)	0.18154 (16)	0.0313 (6)
C19	0.2982 (4)	0.41196 (13)	0.18991 (16)	0.0335 (6)
C20	0.4725 (4)	0.39823 (14)	0.17722 (17)	0.0408 (7)
H20	0.5579	0.4329	0.1821	0.049*
C21	0.5192 (4)	0.33281 (14)	0.15726 (18)	0.0455 (8)
H21	0.6363	0.3236	0.1491	0.055*
C22	0.3929 (4)	0.28132 (13)	0.14944 (18)	0.0414 (7)
H22	0.4252	0.2376	0.1357	0.050*
C23	0.3662 (4)	0.52643 (13)	0.2358 (2)	0.0467 (8)
H23A	0.4226	0.5401	0.1890	0.056*
H23B	0.4595	0.5098	0.2799	0.056*
C24	0.2705 (4)	0.58586 (14)	0.2663 (2)	0.0598 (10)
H24A	0.1764	0.6012	0.2226	0.090*
H24B	0.3550	0.6222	0.2820	0.090*
H24C	0.2187	0.5723	0.3138	0.090*
O5	0.6407 (5)	0.27813 (18)	0.4851 (3)	0.1619 (18)
O6	0.6611 (6)	0.3759 (2)	0.5301 (2)	0.1664 (18)
N3	0.6350 (4)	0.3364 (2)	0.4748 (3)	0.0808 (10)
C25	0.6008 (6)	0.3659 (3)	0.3918 (3)	0.133 (2)
H25A	0.4821	0.3856	0.3815	0.200*
H25B	0.6087	0.3311	0.3511	0.200*
H25C	0.6889	0.4006	0.3877	0.200*

	U11	U22	U33	U12	U13	U23
O1	0.0477 (13)	0.0267 (10)	0.0354 (12)	−0.0027 (8)	0.0084 (10)	−0.0019 (9)
O2	0.0549 (14)	0.0404 (11)	0.0313 (11)	0.0011 (9)	0.0082 (10)	0.0044 (9)
O3	0.0338 (12)	0.0312 (11)	0.0459 (12)	0.0002 (8)	0.0094 (10)	−0.0025 (9)
O4	0.0400 (13)	0.0298 (10)	0.0509 (13)	−0.0062 (9)	0.0106 (10)	−0.0049 (9)
N1	0.0440 (16)	0.0308 (12)	0.0345 (14)	0.0011 (10)	0.0083 (12)	−0.0006 (11)
N2	0.0409 (15)	0.0252 (12)	0.0327 (14)	0.0009 (10)	0.0070 (11)	−0.0007 (10)
C1	0.0424 (18)	0.0322 (15)	0.0321 (16)	−0.0024 (13)	0.0100 (14)	−0.0017 (13)
C2	0.050 (2)	0.0393 (16)	0.0385 (19)	−0.0033 (14)	0.0103 (15)	−0.0039 (14)
C3	0.056 (2)	0.056 (2)	0.0324 (18)	−0.0049 (16)	0.0112 (16)	−0.0025 (15)
C4	0.062 (2)	0.051 (2)	0.0354 (19)	−0.0020 (16)	0.0086 (16)	0.0086 (16)
C5	0.056 (2)	0.0380 (17)	0.042 (2)	0.0000 (14)	0.0088 (16)	0.0043 (15)
C6	0.0391 (18)	0.0341 (16)	0.0310 (16)	−0.0049 (12)	0.0076 (13)	0.0013 (13)
C7	0.0301 (16)	0.0298 (14)	0.0338 (16)	−0.0002 (12)	0.0055 (13)	−0.0008 (13)
C8	0.0299 (16)	0.0268 (14)	0.0360 (16)	0.0012 (11)	0.0045 (13)	−0.0028 (12)
C9	0.0280 (16)	0.0285 (14)	0.0326 (16)	0.0019 (11)	0.0047 (12)	−0.0041 (12)
C10	0.0323 (17)	0.0324 (15)	0.0366 (18)	0.0021 (12)	0.0070 (13)	0.0027 (13)
C11	0.0438 (19)	0.0438 (17)	0.0326 (16)	0.0002 (14)	0.0044 (14)	−0.0019 (14)
C12	0.048 (2)	0.0406 (17)	0.0402 (19)	−0.0014 (14)	0.0052 (15)	−0.0089 (14)
C13	0.0437 (19)	0.0324 (16)	0.0424 (19)	−0.0016 (13)	0.0065 (15)	−0.0027 (13)
C14	0.047 (2)	0.0526 (19)	0.0332 (18)	0.0012 (14)	0.0060 (15)	0.0065 (14)
C15	0.067 (2)	0.053 (2)	0.0408 (19)	0.0023 (16)	0.0111 (17)	0.0124 (15)
C16	0.0391 (18)	0.0275 (14)	0.0405 (17)	0.0010 (12)	0.0088 (14)	−0.0017 (12)
C17	0.0357 (18)	0.0303 (14)	0.0314 (16)	0.0014 (12)	0.0071 (13)	0.0018 (12)
C18	0.0308 (17)	0.0352 (15)	0.0271 (15)	−0.0006 (12)	0.0028 (12)	0.0027 (12)
C19	0.0369 (18)	0.0338 (15)	0.0291 (16)	−0.0024 (13)	0.0041 (13)	0.0001 (12)
C20	0.0394 (19)	0.0452 (17)	0.0384 (17)	−0.0081 (14)	0.0080 (14)	0.0010 (14)
C21	0.0402 (19)	0.0466 (18)	0.052 (2)	0.0019 (15)	0.0148 (16)	−0.0008 (15)
C22	0.043 (2)	0.0357 (16)	0.0463 (19)	0.0018 (14)	0.0101 (15)	−0.0004 (13)
C23	0.042 (2)	0.0415 (17)	0.055 (2)	−0.0142 (14)	0.0040 (16)	−0.0075 (15)
C24	0.059 (2)	0.0447 (19)	0.077 (3)	−0.0144 (16)	0.016 (2)	−0.0212 (17)
O5	0.123 (3)	0.078 (2)	0.279 (5)	−0.026 (2)	0.018 (3)	0.051 (3)
O6	0.212 (5)	0.166 (4)	0.118 (3)	−0.030 (3)	0.021 (3)	−0.050 (3)
N3	0.067 (2)	0.074 (3)	0.098 (3)	−0.0158 (19)	0.006 (2)	0.000 (2)
C25	0.085 (4)	0.232 (6)	0.083 (4)	0.034 (4)	0.017 (3)	0.060 (4)

O1—C9	1.362 (3)	C13—H13	0.9300
O1—H1O	0.92 (4)	C14—C15	1.499 (4)
O2—C10	1.367 (3)	C14—H14A	0.9700
O2—C14	1.431 (3)	C14—H14B	0.9700
O3—C18	1.362 (3)	C15—H15A	0.9600
O3—H3O	0.99 (3)	C15—H15B	0.9600
O4—C19	1.370 (3)	C15—H15C	0.9600
O4—C23	1.434 (3)	C16—C17	1.511 (3)
N1—C7	1.329 (3)	C16—H16A	0.9700
N1—C1	1.386 (3)	C16—H16B	0.9700
N2—C7	1.372 (3)	C17—C22	1.381 (4)
N2—C6	1.385 (3)	C17—C18	1.382 (3)
N2—C16	1.455 (3)	C18—C19	1.403 (3)
C1—C2	1.388 (4)	C19—C20	1.387 (4)
C1—C6	1.395 (3)	C20—C21	1.385 (3)
C2—C3	1.371 (4)	C20—H20	0.9300
C2—H2	0.9300	C21—C22	1.378 (4)
C3—C4	1.399 (4)	C21—H21	0.9300
C3—H3	0.9300	C22—H22	0.9300
C4—C5	1.374 (4)	C23—C24	1.500 (4)
C4—H4	0.9300	C23—H23A	0.9700
C5—C6	1.386 (4)	C23—H23B	0.9700
C5—H5	0.9300	C24—H24A	0.9600
C7—C8	1.462 (4)	C24—H24B	0.9600
C8—C9	1.399 (3)	C24—H24C	0.9600
C8—C13	1.399 (3)	O5—N3	1.157 (4)
C9—C10	1.405 (3)	O6—N3	1.178 (4)
C10—C11	1.370 (3)	N3—C25	1.450 (5)
C11—C12	1.392 (3)	C25—H25A	0.9600
C11—H11	0.9300	C25—H25B	0.9600
C12—C13	1.369 (4)	C25—H25C	0.9600
C12—H12	0.9300
C9—O1—H1O	105 (2)	H14A—C14—H14B	108.6
C10—O2—C14	118.1 (2)	C14—C15—H15A	109.5
C18—O3—H3O	112.0 (18)	C14—C15—H15B	109.5
C19—O4—C23	117.4 (2)	H15A—C15—H15B	109.5
C7—N1—C1	106.0 (2)	C14—C15—H15C	109.5
C7—N2—C6	106.7 (2)	H15A—C15—H15C	109.5
C7—N2—C16	129.8 (2)	H15B—C15—H15C	109.5
C6—N2—C16	123.1 (2)	N2—C16—C17	113.5 (2)
N1—C1—C2	131.0 (2)	N2—C16—H16A	108.9
N1—C1—C6	109.2 (2)	C17—C16—H16A	108.9
C2—C1—C6	119.8 (3)	N2—C16—H16B	108.9
C3—C2—C1	118.1 (3)	C17—C16—H16B	108.9
C3—C2—H2	121.0	H16A—C16—H16B	107.7
C1—C2—H2	121.0	C22—C17—C18	119.5 (2)
C2—C3—C4	121.5 (3)	C22—C17—C16	123.2 (2)
C2—C3—H3	119.2	C18—C17—C16	117.2 (2)
C4—C3—H3	119.2	O3—C18—C17	117.4 (2)
C5—C4—C3	121.3 (3)	O3—C18—C19	122.2 (2)
C5—C4—H4	119.4	C17—C18—C19	120.4 (2)
C3—C4—H4	119.4	O4—C19—C20	125.7 (2)
C4—C5—C6	116.9 (3)	O4—C19—C18	115.1 (2)
C4—C5—H5	121.6	C20—C19—C18	119.2 (2)
C6—C5—H5	121.6	C21—C20—C19	119.9 (3)
N2—C6—C5	131.3 (2)	C21—C20—H20	120.0
N2—C6—C1	106.2 (2)	C19—C20—H20	120.0
C5—C6—C1	122.4 (3)	C22—C21—C20	120.3 (3)
N1—C7—N2	111.9 (2)	C22—C21—H21	119.8
N1—C7—C8	121.6 (2)	C20—C21—H21	119.8
N2—C7—C8	126.5 (2)	C21—C22—C17	120.6 (2)
C9—C8—C13	118.6 (2)	C21—C22—H22	119.7
C9—C8—C7	117.8 (2)	C17—C22—H22	119.7
C13—C8—C7	123.4 (2)	O4—C23—C24	108.0 (2)
O1—C9—C8	122.7 (2)	O4—C23—H23A	110.1
O1—C9—C10	117.2 (2)	C24—C23—H23A	110.1
C8—C9—C10	120.1 (2)	O4—C23—H23B	110.1
O2—C10—C11	126.1 (2)	C24—C23—H23B	110.1
O2—C10—C9	114.0 (2)	H23A—C23—H23B	108.4
C11—C10—C9	119.9 (2)	C23—C24—H24A	109.5
C10—C11—C12	120.0 (3)	C23—C24—H24B	109.5
C10—C11—H11	120.0	H24A—C24—H24B	109.5
C12—C11—H11	120.0	C23—C24—H24C	109.5
C13—C12—C11	120.7 (3)	H24A—C24—H24C	109.5
C13—C12—H12	119.6	H24B—C24—H24C	109.5
C11—C12—H12	119.6	O5—N3—O6	123.0 (5)
C12—C13—C8	120.5 (3)	O5—N3—C25	121.8 (5)
C12—C13—H13	119.7	O6—N3—C25	115.2 (4)
C8—C13—H13	119.7	N3—C25—H25A	109.5
O2—C14—C15	107.1 (2)	N3—C25—H25B	109.5
O2—C14—H14A	110.3	H25A—C25—H25B	109.5
C15—C14—H14A	110.3	N3—C25—H25C	109.5
O2—C14—H14B	110.3	H25A—C25—H25C	109.5
C15—C14—H14B	110.3	H25B—C25—H25C	109.5
C7—N1—C1—C2	179.1 (3)	O1—C9—C10—O2	−3.3 (3)
C7—N1—C1—C6	−1.6 (3)	C8—C9—C10—O2	178.0 (2)
N1—C1—C2—C3	−179.9 (3)	O1—C9—C10—C11	175.6 (2)
C6—C1—C2—C3	0.8 (4)	C8—C9—C10—C11	−3.1 (4)
C1—C2—C3—C4	−0.1 (4)	O2—C10—C11—C12	179.3 (2)
C2—C3—C4—C5	−0.6 (5)	C9—C10—C11—C12	0.5 (4)
C3—C4—C5—C6	0.6 (4)	C10—C11—C12—C13	1.2 (4)
C7—N2—C6—C5	−178.3 (3)	C11—C12—C13—C8	−0.3 (4)
C16—N2—C6—C5	8.6 (4)	C9—C8—C13—C12	−2.2 (4)
C7—N2—C6—C1	1.0 (3)	C7—C8—C13—C12	−178.3 (3)
C16—N2—C6—C1	−172.1 (2)	C10—O2—C14—C15	−176.3 (2)
C4—C5—C6—N2	179.4 (3)	C7—N2—C16—C17	102.3 (3)
C4—C5—C6—C1	0.2 (4)	C6—N2—C16—C17	−86.3 (3)
N1—C1—C6—N2	0.3 (3)	N2—C16—C17—C22	−3.6 (4)
C2—C1—C6—N2	179.8 (2)	N2—C16—C17—C18	177.0 (2)
N1—C1—C6—C5	179.7 (3)	C22—C17—C18—O3	−179.6 (2)
C2—C1—C6—C5	−0.9 (4)	C16—C17—C18—O3	−0.2 (4)
C1—N1—C7—N2	2.3 (3)	C22—C17—C18—C19	−0.8 (4)
C1—N1—C7—C8	−178.9 (2)	C16—C17—C18—C19	178.6 (2)
C6—N2—C7—N1	−2.1 (3)	C23—O4—C19—C20	−12.0 (4)
C16—N2—C7—N1	170.3 (2)	C23—O4—C19—C18	168.1 (2)
C6—N2—C7—C8	179.1 (2)	O3—C18—C19—O4	−0.6 (4)
C16—N2—C7—C8	−8.4 (4)	C17—C18—C19—O4	−179.2 (2)
N1—C7—C8—C9	−25.1 (4)	O3—C18—C19—C20	179.5 (2)
N2—C7—C8—C9	153.6 (2)	C17—C18—C19—C20	0.8 (4)
N1—C7—C8—C13	151.1 (3)	O4—C19—C20—C21	179.5 (3)
N2—C7—C8—C13	−30.3 (4)	C18—C19—C20—C21	−0.6 (4)
C13—C8—C9—O1	−174.7 (2)	C19—C20—C21—C22	0.4 (4)
C7—C8—C9—O1	1.6 (4)	C20—C21—C22—C17	−0.4 (4)
C13—C8—C9—C10	3.9 (4)	C18—C17—C22—C21	0.6 (4)
C7—C8—C9—C10	−179.8 (2)	C16—C17—C22—C21	−178.7 (3)
C14—O2—C10—C11	−4.9 (4)	C19—O4—C23—C24	−172.3 (2)
C14—O2—C10—C9	173.9 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···N1	0.92 (4)	1.75 (4)	2.596 (3)	152 (3)
O3—H3O···O4	0.99 (3)	2.27 (3)	2.710 (2)	106 (2)
O3—H3O···O1i	0.99 (3)	1.91 (3)	2.819 (2)	151 (2)
O3—H3O···O2i	0.99 (3)	2.36 (3)	3.012 (3)	122 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O⋯N1	0.92 (4)	1.75 (4)	2.596 (3)	152 (3)
O3—H3O⋯O4	0.99 (3)	2.27 (3)	2.710 (2)	106 (2)
O3—H3O⋯O1i	0.99 (3)	1.91 (3)	2.819 (2)	151 (2)
O3—H3O⋯O2i	0.99 (3)	2.36 (3)	3.012 (3)	122 (2)

Symmetry code: (i) .