The triclinic form of di-μ-aqua-bis-[diaqua-bis-(thio-cyanato-κN)iron(II)]-1,4-bis-(4H-1,2,4-triazol-4-yl)benzene (1/3).

In the title compound, [Fe(2)(NCS)(4)(H(2)O)(6)]·3C(10)H(8)N(6), the centrosymmetric dinuclear complex contains two Fe(II) ions bridged by two aqua ligand O atoms, forming a four-membered ring. The slightly distorted octa-hedral coordination environment of the two Fe(II) ions is completed by two monodentate aqua ligands and two thio-cyanate ligands. One of the 1,4-bis-(4H-1,2,4-triazol-4-yl)benzene mol-ecules lies across an inversion center. In the crystal, O-H⋯N hydrogen bonds connect the components, forming a two-dimensional network parallel to (011). In addition, π-π stacking inter-actions involving the benzene and triazole rings, with centroid-centroid distances in the range 3.502 (5)-3.787 (6) Å, connect the two-dimensional hydrogen-bonded network into a three-dimensional network.

Related literature

For details of compounds containing a diiron center, see: Hsu et al. (1999 ▶); Zheng et al. (1999 ▶); MacMurdo et al. (2000 ▶); Yoon et al. (2004 ▶). For related multicompent di­oxy­gen dependent enzymes including toluene mono­oxygenase, see: Sazinsky et al. (2004 ▶). For related multicompent di­oxy­gen dependent enzymes including the R 2 subunit of ribonucleotide reductase, see: Nordlund & Eklund (1993 ▶); Stubbe & Van der Donk (1998 ▶). For the monoclinic form of the title compound, see: Liu et al. (2012 ▶).

.

Experimental

Crystal data

[Fe2(NCS)4(H2O)6]·3C10H8N6

M = 1088.79

Triclinic,

a = 7.8335 (6) Å

b = 10.9081 (8) Å

c = 13.8067 (10) Å

α = 68.999 (1)°

β = 84.952 (1)°

γ = 83.355 (1)°

V = 1092.62 (14) Å3

Z = 1

Mo Kα radiation

μ = 0.93 mm−1

T = 173 K

0.18 × 0.14 × 0.13 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.851, T max = 0.889

5619 measured reflections

3827 independent reflections

3435 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.077

S = 1.03

3827 reflections

307 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.30 e Å−3

Δρmin = −0.43 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶) and DIAMOND (Brandenburg, 1999 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812026141/lh5483sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812026141/lh5483Isup2.hkl

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

[Fe2(NCS)4(H2O)6]·3C10H8N6	Z = 1
Mr = 1088.79	F(000) = 558
Triclinic, P1	Dx = 1.655 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.8335 (6) Å	Cell parameters from 2875 reflections
b = 10.9081 (8) Å	θ = 3.0–28.4°
c = 13.8067 (10) Å	µ = 0.93 mm−1
α = 68.999 (1)°	T = 173 K
β = 84.952 (1)°	Block, colourless
γ = 83.355 (1)°	0.18 × 0.14 × 0.13 mm
V = 1092.62 (14) Å3

Bruker APEXII CCD diffractometer	3827 independent reflections
Radiation source: fine-focus sealed tube	3435 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.019
φ and ω scans	θmax = 25.0°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→9
Tmin = 0.851, Tmax = 0.889	k = −9→12
5619 measured reflections	l = −15→16

Refinement on F2	2 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.031	w = 1/[σ2(Fo2) + (0.0345P)2 + 0.7404P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.077	(Δ/σ)max = 0.001
S = 1.03	Δρmax = 0.30 e Å−3
3827 reflections	Δρmin = −0.43 e Å−3
307 parameters

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
Fe1	0.93995 (4)	0.61553 (3)	0.06003 (2)	0.01245 (10)
S1	0.94951 (7)	0.98407 (6)	−0.27085 (4)	0.01874 (14)
S2	0.94707 (7)	0.29730 (6)	0.41566 (4)	0.01899 (14)
O1	1.08753 (19)	0.72399 (15)	0.11568 (11)	0.0168 (3)
H1A	1.1503	0.6859	0.1662	0.025*
H1B	1.1432	0.7829	0.0721	0.025*
O2	1.17972 (18)	0.51345 (14)	0.00652 (10)	0.0135 (3)
H2A	1.2497	0.5774	−0.0469	0.020*
H2B	1.2517	0.4605	0.0653	0.020*
O3	0.68912 (19)	0.68356 (15)	0.09608 (11)	0.0172 (3)
H3A	0.6264	0.7424	0.0535	0.026*
H3B	0.6237	0.6411	0.1452	0.026*
N1	0.3803 (2)	0.43716 (17)	0.42713 (13)	0.0149 (4)
N2	0.4701 (2)	0.55412 (18)	0.26843 (13)	0.0166 (4)
N3	0.2969 (2)	0.58853 (19)	0.28071 (14)	0.0212 (4)
N4	0.3748 (2)	0.05660 (17)	0.83062 (13)	0.0133 (4)
N5	0.4598 (2)	−0.11802 (18)	0.96406 (13)	0.0165 (4)
N6	0.2857 (2)	−0.08517 (18)	0.97992 (14)	0.0188 (4)
N7	0.5005 (2)	0.19396 (17)	0.29899 (13)	0.0116 (4)
N8	0.5907 (2)	0.33244 (18)	0.14775 (13)	0.0151 (4)
N9	0.4119 (2)	0.34901 (17)	0.15464 (13)	0.0150 (4)
N10	0.9418 (2)	0.76782 (18)	−0.08416 (14)	0.0164 (4)
N11	0.9443 (2)	0.46757 (18)	0.20753 (14)	0.0168 (4)
C1	0.5168 (3)	0.4650 (2)	0.35647 (16)	0.0172 (5)
H1	0.6307	0.4247	0.3696	0.021*
C2	0.2474 (3)	0.5182 (2)	0.37532 (17)	0.0207 (5)
H2	0.1332	0.5231	0.4041	0.025*
C3	0.3786 (3)	0.3430 (2)	0.53126 (16)	0.0138 (4)
C4	0.2299 (3)	0.3324 (2)	0.59539 (16)	0.0173 (5)
H4	0.1291	0.3888	0.5708	0.021*
C5	0.2281 (3)	0.2398 (2)	0.69513 (16)	0.0159 (5)
H5	0.1264	0.2325	0.7390	0.019*
C6	0.3758 (3)	0.1580 (2)	0.73034 (15)	0.0135 (4)
C7	0.5257 (3)	0.1709 (2)	0.66666 (16)	0.0160 (5)
H7	0.6275	0.1161	0.6917	0.019*
C8	0.5268 (3)	0.2630 (2)	0.56752 (16)	0.0159 (5)
H8	0.6291	0.2717	0.5241	0.019*
C9	0.5101 (3)	−0.0323 (2)	0.87559 (16)	0.0167 (5)
H9	0.6244	−0.0314	0.8462	0.020*
C10	0.2392 (3)	0.0185 (2)	0.89994 (16)	0.0173 (5)
H10	0.1260	0.0614	0.8913	0.021*
C11	0.6395 (3)	0.2405 (2)	0.23378 (16)	0.0146 (5)
H11	0.7560	0.2098	0.2493	0.017*
C12	0.3619 (3)	0.2663 (2)	0.24462 (16)	0.0144 (5)
H12	0.2452	0.2573	0.2692	0.017*
C13	0.5004 (3)	0.0950 (2)	0.40112 (15)	0.0119 (4)
C14	0.3452 (3)	0.0654 (2)	0.45848 (16)	0.0147 (5)
H14	0.2398	0.1101	0.4297	0.018*
C15	0.6553 (3)	0.0293 (2)	0.44258 (16)	0.0147 (5)
H15	0.7608	0.0493	0.4032	0.018*
C16	0.9452 (3)	0.8577 (2)	−0.16137 (16)	0.0128 (4)
C17	0.9453 (3)	0.3973 (2)	0.29352 (16)	0.0139 (4)

	U11	U22	U33	U12	U13	U23
Fe1	0.01271 (17)	0.01269 (17)	0.01021 (16)	−0.00163 (13)	−0.00107 (12)	−0.00164 (13)
S1	0.0169 (3)	0.0181 (3)	0.0141 (3)	−0.0007 (2)	−0.0003 (2)	0.0026 (2)
S2	0.0171 (3)	0.0201 (3)	0.0129 (3)	0.0002 (2)	−0.0008 (2)	0.0019 (2)
O1	0.0173 (8)	0.0179 (8)	0.0124 (7)	−0.0047 (6)	−0.0022 (6)	−0.0008 (6)
O2	0.0135 (7)	0.0140 (8)	0.0103 (7)	−0.0012 (6)	−0.0013 (6)	−0.0008 (6)
O3	0.0154 (8)	0.0180 (8)	0.0118 (7)	0.0000 (6)	0.0011 (6)	0.0017 (6)
N1	0.0184 (10)	0.0130 (9)	0.0108 (9)	−0.0002 (8)	−0.0013 (8)	−0.0015 (7)
N2	0.0207 (10)	0.0147 (10)	0.0144 (9)	−0.0022 (8)	−0.0001 (8)	−0.0050 (8)
N3	0.0197 (10)	0.0221 (11)	0.0194 (10)	−0.0035 (8)	−0.0049 (8)	−0.0029 (8)
N4	0.0148 (9)	0.0123 (9)	0.0118 (8)	−0.0008 (8)	−0.0006 (7)	−0.0033 (7)
N5	0.0194 (10)	0.0140 (9)	0.0153 (9)	0.0001 (8)	−0.0028 (8)	−0.0041 (8)
N6	0.0207 (10)	0.0175 (10)	0.0161 (9)	−0.0044 (8)	−0.0018 (8)	−0.0024 (8)
N7	0.0128 (9)	0.0110 (9)	0.0100 (8)	−0.0010 (7)	−0.0014 (7)	−0.0023 (7)
N8	0.0150 (9)	0.0140 (9)	0.0149 (9)	−0.0017 (8)	−0.0024 (7)	−0.0028 (8)
N9	0.0164 (10)	0.0130 (9)	0.0139 (9)	−0.0017 (8)	−0.0032 (7)	−0.0022 (8)
N10	0.0132 (10)	0.0173 (10)	0.0171 (9)	0.0003 (8)	−0.0016 (8)	−0.0042 (8)
N11	0.0143 (10)	0.0187 (10)	0.0162 (9)	−0.0023 (8)	−0.0004 (8)	−0.0043 (8)
C1	0.0179 (12)	0.0184 (12)	0.0156 (11)	−0.0025 (9)	0.0015 (9)	−0.0066 (9)
C2	0.0167 (12)	0.0229 (13)	0.0179 (11)	−0.0020 (10)	−0.0011 (10)	−0.0014 (10)
C3	0.0172 (11)	0.0125 (11)	0.0131 (10)	−0.0031 (9)	−0.0010 (9)	−0.0055 (9)
C4	0.0140 (11)	0.0176 (12)	0.0161 (11)	0.0034 (9)	−0.0016 (9)	−0.0020 (9)
C5	0.0121 (11)	0.0179 (12)	0.0150 (10)	−0.0004 (9)	0.0025 (9)	−0.0034 (9)
C6	0.0178 (11)	0.0121 (11)	0.0119 (10)	−0.0026 (9)	−0.0019 (9)	−0.0049 (9)
C7	0.0151 (11)	0.0154 (11)	0.0165 (11)	0.0022 (9)	−0.0026 (9)	−0.0050 (9)
C8	0.0135 (11)	0.0171 (11)	0.0159 (11)	−0.0011 (9)	0.0010 (9)	−0.0050 (9)
C9	0.0182 (12)	0.0160 (11)	0.0156 (11)	0.0008 (9)	−0.0043 (9)	−0.0051 (9)
C10	0.0154 (12)	0.0182 (12)	0.0161 (11)	−0.0025 (9)	−0.0014 (9)	−0.0029 (9)
C11	0.0134 (11)	0.0164 (11)	0.0130 (10)	−0.0021 (9)	0.0000 (9)	−0.0040 (9)
C12	0.0149 (11)	0.0144 (11)	0.0130 (10)	0.0001 (9)	−0.0030 (9)	−0.0037 (9)
C13	0.0151 (11)	0.0104 (10)	0.0105 (10)	−0.0022 (9)	−0.0026 (8)	−0.0032 (8)
C14	0.0114 (11)	0.0158 (11)	0.0153 (10)	0.0000 (9)	−0.0023 (9)	−0.0036 (9)
C15	0.0125 (11)	0.0165 (11)	0.0137 (10)	−0.0018 (9)	0.0014 (9)	−0.0039 (9)
C16	0.0104 (10)	0.0146 (10)	0.0131 (9)	0.0001 (9)	−0.0005 (8)	−0.0048 (7)
C17	0.0121 (11)	0.0137 (11)	0.0148 (9)	−0.0002 (9)	0.0003 (9)	−0.0041 (8)

Fe1—N10	2.0865 (18)	N7—C13	1.436 (3)
Fe1—N11	2.0968 (18)	N8—C11	1.304 (3)
Fe1—O3	2.1011 (15)	N8—N9	1.391 (3)
Fe1—O1	2.1097 (14)	N9—C12	1.305 (3)
Fe1—O2i	2.2552 (14)	N10—C16	1.162 (3)
Fe1—O2	2.2748 (15)	N11—C17	1.160 (3)
S1—C16	1.641 (2)	C1—H1	0.9500
S2—C17	1.648 (2)	C2—H2	0.9500
O1—H1A	0.8401	C3—C8	1.384 (3)
O1—H1B	0.8401	C3—C4	1.389 (3)
O2—Fe1i	2.2552 (14)	C4—C5	1.385 (3)
O2—H2A	0.9900	C4—H4	0.9500
O2—H2B	0.9900	C5—C6	1.386 (3)
O3—H3A	0.8401	C5—H5	0.9500
O3—H3B	0.8401	C6—C7	1.393 (3)
N1—C2	1.357 (3)	C7—C8	1.377 (3)
N1—C1	1.366 (3)	C7—H7	0.9500
N1—C3	1.437 (3)	C8—H8	0.9500
N2—C1	1.306 (3)	C9—H9	0.9500
N2—N3	1.377 (3)	C10—H10	0.9500
N3—C2	1.306 (3)	C11—H11	0.9500
N4—C10	1.362 (3)	C12—H12	0.9500
N4—C9	1.377 (3)	C13—C15	1.393 (3)
N4—C6	1.430 (3)	C13—C14	1.396 (3)
N5—C9	1.305 (3)	C14—C15ii	1.386 (3)
N5—N6	1.388 (3)	C14—H14	0.9500
N6—C10	1.308 (3)	C15—C14ii	1.386 (3)
N7—C11	1.372 (3)	C15—H15	0.9500
N7—C12	1.373 (3)
N10—Fe1—N11	177.40 (7)	N1—C1—H1	124.5
N10—Fe1—O3	90.67 (6)	N3—C2—N1	111.2 (2)
N11—Fe1—O3	89.72 (6)	N3—C2—H2	124.4
N10—Fe1—O1	88.84 (6)	N1—C2—H2	124.4
N11—Fe1—O1	88.55 (6)	C8—C3—C4	120.1 (2)
O3—Fe1—O1	101.03 (6)	C8—C3—N1	119.39 (19)
N10—Fe1—O2i	91.03 (6)	C4—C3—N1	120.48 (19)
N11—Fe1—O2i	91.56 (6)	C5—C4—C3	120.2 (2)
O3—Fe1—O2i	87.55 (6)	C5—C4—H4	119.9
O1—Fe1—O2i	171.43 (6)	C3—C4—H4	119.9
N10—Fe1—O2	89.61 (6)	C4—C5—C6	119.4 (2)
N11—Fe1—O2	90.60 (6)	C4—C5—H5	120.3
O3—Fe1—O2	166.90 (5)	C6—C5—H5	120.3
O1—Fe1—O2	92.07 (6)	C5—C6—C7	120.17 (19)
O2i—Fe1—O2	79.35 (5)	C5—C6—N4	120.60 (19)
Fe1—O1—H1A	120.8	C7—C6—N4	119.19 (19)
Fe1—O1—H1B	118.2	C8—C7—C6	120.2 (2)
H1A—O1—H1B	106.9	C8—C7—H7	119.9
Fe1i—O2—Fe1	100.65 (5)	C6—C7—H7	119.9
Fe1i—O2—H2A	111.6	C7—C8—C3	119.8 (2)
Fe1—O2—H2A	111.6	C7—C8—H8	120.1
Fe1i—O2—H2B	111.6	C3—C8—H8	120.1
Fe1—O2—H2B	111.6	N5—C9—N4	110.8 (2)
H2A—O2—H2B	109.4	N5—C9—H9	124.6
Fe1—O3—H3A	124.5	N4—C9—H9	124.6
Fe1—O3—H3B	125.3	N6—C10—N4	111.0 (2)
H3A—O3—H3B	106.9	N6—C10—H10	124.5
C2—N1—C1	103.71 (18)	N4—C10—H10	124.5
C2—N1—C3	128.44 (19)	N8—C11—N7	111.06 (19)
C1—N1—C3	127.84 (18)	N8—C11—H11	124.5
C1—N2—N3	106.87 (18)	N7—C11—H11	124.5
C2—N3—N2	107.16 (18)	N9—C12—N7	110.95 (19)
C10—N4—C9	104.00 (18)	N9—C12—H12	124.5
C10—N4—C6	128.60 (18)	N7—C12—H12	124.5
C9—N4—C6	127.22 (18)	C15—C13—C14	120.34 (19)
C9—N5—N6	107.03 (17)	C15—C13—N7	119.82 (19)
C10—N6—N5	107.25 (18)	C14—C13—N7	119.84 (18)
C11—N7—C12	103.73 (17)	C15ii—C14—C13	120.01 (19)
C11—N7—C13	128.06 (17)	C15ii—C14—H14	120.0
C12—N7—C13	128.19 (18)	C13—C14—H14	120.0
C11—N8—N9	107.13 (17)	C14ii—C15—C13	119.7 (2)
C12—N9—N8	107.12 (17)	C14ii—C15—H15	120.2
C16—N10—Fe1	175.78 (17)	C13—C15—H15	120.2
C17—N11—Fe1	172.21 (17)	N10—C16—S1	179.6 (2)
N2—C1—N1	111.1 (2)	N11—C17—S2	179.9 (3)
N2—C1—H1	124.5
N10—Fe1—O2—Fe1i	−91.12 (6)	C4—C5—C6—N4	−176.34 (18)
N11—Fe1—O2—Fe1i	91.48 (6)	C10—N4—C6—C5	5.2 (3)
O3—Fe1—O2—Fe1i	0.2 (3)	C9—N4—C6—C5	179.4 (2)
O1—Fe1—O2—Fe1i	−179.95 (5)	C10—N4—C6—C7	−172.6 (2)
O2i—Fe1—O2—Fe1i	0.0	C9—N4—C6—C7	1.7 (3)
C1—N2—N3—C2	−0.2 (2)	C5—C6—C7—C8	−1.5 (3)
C9—N5—N6—C10	0.3 (2)	N4—C6—C7—C8	176.30 (18)
C11—N8—N9—C12	0.1 (2)	C6—C7—C8—C3	0.1 (3)
N11—Fe1—N10—C16	−18 (3)	C4—C3—C8—C7	1.4 (3)
O3—Fe1—N10—C16	80 (2)	N1—C3—C8—C7	−178.93 (18)
O1—Fe1—N10—C16	−21 (2)	N6—N5—C9—N4	−0.7 (2)
O2i—Fe1—N10—C16	168 (2)	C10—N4—C9—N5	0.8 (2)
O2—Fe1—N10—C16	−113 (2)	C6—N4—C9—N5	−174.65 (18)
N10—Fe1—N11—C17	34 (2)	N5—N6—C10—N4	0.2 (2)
O3—Fe1—N11—C17	−64.2 (12)	C9—N4—C10—N6	−0.6 (2)
O1—Fe1—N11—C17	36.9 (12)	C6—N4—C10—N6	174.75 (18)
O2i—Fe1—N11—C17	−151.7 (12)	N9—N8—C11—N7	0.0 (2)
O2—Fe1—N11—C17	128.9 (12)	C12—N7—C11—N8	0.0 (2)
N3—N2—C1—N1	0.7 (2)	C13—N7—C11—N8	−178.74 (18)
C2—N1—C1—N2	−0.9 (2)	N8—N9—C12—N7	−0.1 (2)
C3—N1—C1—N2	178.46 (18)	C11—N7—C12—N9	0.1 (2)
N2—N3—C2—N1	−0.3 (3)	C13—N7—C12—N9	178.79 (18)
C1—N1—C2—N3	0.7 (2)	C11—N7—C13—C15	−3.3 (3)
C3—N1—C2—N3	−178.62 (19)	C12—N7—C13—C15	178.31 (19)
C2—N1—C3—C8	175.7 (2)	C11—N7—C13—C14	176.49 (19)
C1—N1—C3—C8	−3.5 (3)	C12—N7—C13—C14	−1.9 (3)
C2—N1—C3—C4	−4.6 (3)	C15—C13—C14—C15ii	0.3 (3)
C1—N1—C3—C4	176.2 (2)	N7—C13—C14—C15ii	−179.45 (18)
C8—C3—C4—C5	−1.4 (3)	C14—C13—C15—C14ii	−0.3 (3)
N1—C3—C4—C5	178.86 (19)	N7—C13—C15—C14ii	179.45 (18)
C3—C4—C5—C6	0.0 (3)	Fe1—N10—C16—S1	−174 (100)
C4—C5—C6—C7	1.4 (3)	Fe1—N11—C17—S2	−123 (100)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···N3iii	0.84	1.94	2.784 (2)	177
O1—H1B···N6iv	0.84	1.94	2.774 (2)	175
O2—H2A···N8i	0.99	1.86	2.838 (2)	168
O2—H2B···N9iii	0.99	1.85	2.824 (2)	168
O3—H3A···N5v	0.84	2.01	2.843 (2)	174
O3—H3B···N2	0.84	2.00	2.834 (2)	174

Table 1

Selected bond lengths (Å)

Fe1—N10	2.0865 (18)
Fe1—N11	2.0968 (18)
Fe1—O3	2.1011 (15)
Fe1—O1	2.1097 (14)
Fe1—O2i	2.2552 (14)
Fe1—O2	2.2748 (15)

Symmetry code: (i) .

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯N3ii	0.84	1.94	2.784 (2)	177
O1—H1B⋯N6iii	0.84	1.94	2.774 (2)	175
O2—H2A⋯N8i	0.99	1.86	2.838 (2)	168
O2—H2B⋯N9ii	0.99	1.85	2.824 (2)	168
O3—H3A⋯N5iv	0.84	2.01	2.843 (2)	174
O3—H3B⋯N2	0.84	2.00	2.834 (2)	174

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