4-Nitro-2-(1H-tetrazol-1-yl)­phenol

There are two symmetry-independent mol­ecules in the unit cell of the title compound, C₇H₅N₅O₃. The tetrazole and phenyl rings are essentially planar and are not coplanar in either mol­ecule [dihedral angles 30.2 (1) and 7.0 (1)°]. In the structure, four mol­ecules are connected by O—H...N bridges, forming four-membered molecular aggregates which are linked together by a complex three-dimensional hydrogen-bond network.

S1. Comment

1-Monosubstituted aryltetrazoles have attracted considerable theoretical and experimental interest. On the one hand, they are used as valuable intermediates in the synthesis of arylcyanamides (Gaponik et al., 1990) and different nitrogen-containing heterocycles (Voitekhovich et al., 2001). On the other hand, they attract interest as models for investigation of the interaction between tetrazole and phenyl rings. Previously, only the structures of 1-phenyltetrazole (Matsunaga et al., 1999) and 1-(2,4,6-trimethylphenyl)tetrazole (Lyakhov et al., 2000) have been described. In this paper, we present the crystal structure of a new compound, 4-Nitro-2-(1H-tetrazol-1-yl)phenol, (I). There are two symmetry-independent molecules in the structure denoted by letters A and B.

The tetrazole rings of molecules A and B have very similar geometries; they are planar to within 0.004 (2) and 0.005 (2) Å, respectively. Endocyclic angles vary from 105.5 (1) to 111.1 (1)° and from 106.1 (1) to 110.6 (1)° for molecules A and B, respectively. The N1—N2 and N3—N4 bonds are similar and longer than N2—N3, while the C5—N1 bond is longer than C5—N4 in both molecules. All the formal single endocyclic bonds are considerably shorter than those usually found for normal single bonds, but somewhat longer than normal double bonds (International Tables for Crystallography, 1992, Vol. C, pp. 707–791). This suggests that there is some conjugation in the tetrazole rings of (I), however, significant differences in the endocyclic bond lengths show that there is still considerable localization of charge within the ring.

The bond distances and angles in the phenyl fragments of (I) are consistent with those observed previously. The rings nearly planar to within 0.009 (1) and 0.008 (1) Å for molecules A and B, respectively.

The phenyl and tetrazole rings are not coplanar in either molecule, the dihedral angle between them being 30.2 (1) and 7.0 (1)° in molecules A and B, respectively. To compare these values with that of a free molecule of (I), an ab initio calculation of a single molecule in the 6–311 G^** basis set using the GAMESS program (Schmidt et al., 1993) was carried out. Geometry optimization with respect to all variables results in a dihedral angle between the phenyl and tetrazole rings of 39.6°. It should be noted that in the crystal of 1-phenyltetrazole, the dihedral angle between the rings is 11.8 (1)° (Matsunaga et al., 1999), whereas the angle of 38.6° was obtained from an MP2/6–31 G^* calculation for a free molecule of 1-phenyltetrazole (Matsunaga et al., 1999). The introduction of an ortho-substituent on the phenyl ring must result in more steric hindrance compared with 1-phenyltetrazole and, as a result, the dihedral angle between the rings increases. Such s situation is also seen in the crystal structure of 1-(2,4,6-trimethylphenyl)tetrazole, where the dihedral angle is 69.07 (9)° (Lyakhov et al., 2000), and also in molecule A of (I). In the case of molecule B of (I), a rather small dihedral angle is obtained. Taking these results into account, it may be presumed that the decrease in the dihedral angle in the crystal is due to molecular packing. In the structure of (I), this effect is larger for molecule B than for molecule A.

From an inspection of the packing of the molecules in (I), the following may be noted. There are two types of hydrogen bonds, O1A—H1A···N4B and O1B—H1B···N4A, between molecules A and B, resulting in the formation of four-membered aggregates in the structure (Fig. 2). C8B—H8B···N3A interactions may be considered as additional weak hydrogen bonds between molecules A and B in the four-membered aggregates. Connection of these aggregates is achieved mainly through C9A—H9A···N2B hydrogen bonds (N2A does not form similar bonds). There are also C—H···O contacts (Desiraju, 1996) between the nitro O atoms and the H atoms of the phenyl rings, thereby forming an additional connection between the aggregates. The molecules in the structure of (I) are thus linked together by a complex three-dimensional hydrogen-bond network.

S2. Experimental

The title compound was prepared by heterocyclization of 2-amino-4-nitrophenol with ethyl orthoformate and sodium azide in acetic acid (Voitekhovich et al., 2001). Single crystals were grown by slow crystallization from an acetonitrile solution.

S3. Refinement

H-atom positions were found from the ΔF map and all associated parameters were refined freely [C—H = 0.92 (2)–0.99 (2) Å].

Computing details

Data collection: R3m Software (Nicolet, 1980); cell refinement: R3m Software; data reduction: R3m Software; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 1999); software used to prepare material for publication: SHELXL97.

Figures

	Fig. 1. ORTEP-3 drawing (Farrugia, 1997) of molecule A of (I) with the atom-numbering scheme; for molecule B, substitute the A suffixes with B). Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as spheres of arbitrary radii.
	Fig. 2. [100] view of the four-membered aggregate in the structure of (I). Hydrogen-bonding bridges between the molecules are shown by dashed lines.
	Fig. 3. Packing diagram of the title compound.

1-(2-hydroxy-5-nitrophenyl)-1H-tetrazole

Crystal data

C7H5N5O3	Z = 4
Mr = 207.16	F(000) = 424
Triclinic, P1	Dx = 1.592 Mg m^−3
a = 7.116 (2) Å	Mo Kα radiation, λ = 0.71069 Å
b = 9.452 (2) Å	Cell parameters from 25 reflections
c = 13.895 (3) Å	θ = 12.5–19.8°
α = 86.43 (2)°	µ = 0.13 mm^−1
β = 84.17 (2)°	T = 293 K
γ = 68.42 (2)°	Prism, colourless
V = 864.3 (4) Å^3	0.54 × 0.40 × 0.30 mm

Data collection

Nicolet R3m four-circle diffractometer	Rint = 0.019
Radiation source: fine-focus sealed tube	θmax = 30.1°, θmin = 1.5°
Graphite monochromator	h = 0→10
ω/2θ scans	k = −12→13
5619 measured reflections	l = −19→19
5062 independent reflections	3 standard reflections every 100 reflections
3704 reflections with I > 2σ(I)	intensity decay: 0.1%

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.045	Hydrogen site location: difference Fourier map
wR(F^2) = 0.143	All H-atom parameters refined
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0837P)^2 + 0.0881P] where P = (Fo^2 + 2Fc^2)/3
5062 reflections	(Δ/σ)max = 0.001
311 parameters	Δρmax = 0.25 e Å^−3
0 restraints	Δρmin = −0.27 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N1A	−0.23274 (18)	0.27927 (11)	0.65678 (7)	0.0391 (2)
N2A	−0.1978 (3)	0.13495 (15)	0.63400 (10)	0.0790 (6)
N3A	−0.1855 (4)	0.05921 (16)	0.71514 (11)	0.0901 (7)
N4A	−0.2115 (2)	0.15010 (14)	0.79045 (9)	0.0538 (3)
C5A	−0.2415 (3)	0.28493 (17)	0.75238 (9)	0.0490 (3)
H5A	−0.263 (3)	0.370 (3)	0.7874 (17)	0.080 (6)*
C6A	−0.2466 (2)	0.39313 (13)	0.58251 (8)	0.0345 (2)
C7A	−0.3695 (2)	0.54479 (13)	0.60096 (8)	0.0365 (3)
C8A	−0.3799 (2)	0.65539 (14)	0.52821 (9)	0.0410 (3)
H8A	−0.469 (3)	0.760 (2)	0.5431 (14)	0.059 (5)*
C9A	−0.2735 (2)	0.61563 (15)	0.43936 (9)	0.0403 (3)
H9A	−0.279 (3)	0.694 (2)	0.3885 (12)	0.052 (5)*
C10A	−0.1573 (2)	0.46415 (14)	0.42333 (8)	0.0365 (3)
C11A	−0.1411 (2)	0.35108 (14)	0.49369 (8)	0.0368 (3)
H11A	−0.052 (3)	0.245 (2)	0.4815 (12)	0.048 (4)*
N12A	−0.0407 (2)	0.42126 (14)	0.33021 (8)	0.0465 (3)
O1A	−0.47239 (18)	0.57488 (12)	0.68793 (7)	0.0496 (3)
H1A	−0.527 (4)	0.677 (3)	0.6941 (17)	0.088 (7)*
O2A	−0.0357 (2)	0.52364 (14)	0.27241 (7)	0.0590 (3)
O3A	0.0505 (3)	0.28802 (15)	0.31489 (9)	0.0869 (5)
N1B	0.29712 (18)	0.04553 (11)	0.83583 (7)	0.0390 (2)
N2B	0.3183 (3)	0.10098 (16)	0.74517 (9)	0.0747 (5)
N3B	0.3500 (4)	−0.00811 (17)	0.68734 (10)	0.0808 (6)
N4B	0.3511 (2)	−0.13475 (14)	0.73721 (9)	0.0543 (3)
C5B	0.3167 (3)	−0.09933 (15)	0.82844 (10)	0.0465 (3)
H5B	0.301 (3)	−0.168 (2)	0.8801 (14)	0.063 (5)*
C6B	0.26941 (19)	0.13924 (13)	0.91701 (8)	0.0339 (2)
C7B	0.2350 (2)	0.08549 (13)	1.01118 (8)	0.0353 (3)
C8B	0.2084 (2)	0.18041 (15)	1.08861 (9)	0.0421 (3)
H8B	0.183 (3)	0.1464 (19)	1.1551 (12)	0.046 (4)*
C9B	0.2206 (2)	0.32217 (15)	1.07342 (9)	0.0419 (3)
H9B	0.204 (3)	0.387 (2)	1.1268 (14)	0.061 (5)*
C10B	0.25793 (19)	0.37022 (13)	0.97979 (9)	0.0358 (3)
C11B	0.2813 (2)	0.28149 (13)	0.90095 (8)	0.0353 (2)
H11B	0.301 (2)	0.3158 (19)	0.8370 (12)	0.045 (4)*
N12B	0.27468 (19)	0.51941 (12)	0.96311 (9)	0.0429 (3)
O1B	0.23081 (17)	−0.05484 (10)	1.02257 (7)	0.0473 (3)
H1B	0.222 (3)	−0.078 (3)	1.0888 (17)	0.082 (7)*
O2B	0.2482 (2)	0.59981 (13)	1.03256 (9)	0.0621 (3)
O3B	0.3140 (2)	0.55774 (13)	0.88040 (8)	0.0649 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1A	0.0570 (7)	0.0298 (5)	0.0302 (5)	−0.0179 (4)	0.0041 (4)	0.0024 (4)
N2A	0.1544 (17)	0.0322 (6)	0.0437 (7)	−0.0302 (8)	0.0071 (9)	−0.0001 (5)
N3A	0.173 (2)	0.0363 (7)	0.0498 (8)	−0.0312 (10)	0.0084 (10)	0.0081 (6)
N4A	0.0795 (9)	0.0423 (6)	0.0375 (6)	−0.0237 (6)	0.0040 (6)	0.0104 (5)
C5A	0.0789 (10)	0.0422 (7)	0.0301 (6)	−0.0294 (7)	0.0013 (6)	0.0054 (5)
C6A	0.0477 (7)	0.0312 (5)	0.0267 (5)	−0.0184 (5)	0.0009 (4)	0.0019 (4)
C7A	0.0487 (7)	0.0335 (5)	0.0286 (5)	−0.0181 (5)	0.0033 (5)	−0.0016 (4)
C8A	0.0530 (8)	0.0311 (6)	0.0379 (6)	−0.0155 (5)	−0.0003 (5)	0.0024 (4)
C9A	0.0538 (8)	0.0376 (6)	0.0322 (5)	−0.0211 (5)	−0.0029 (5)	0.0066 (4)
C10A	0.0486 (7)	0.0402 (6)	0.0244 (5)	−0.0218 (5)	0.0013 (4)	0.0006 (4)
C11A	0.0482 (7)	0.0342 (6)	0.0288 (5)	−0.0173 (5)	0.0019 (5)	−0.0007 (4)
N12A	0.0655 (8)	0.0511 (7)	0.0264 (5)	−0.0274 (6)	0.0044 (5)	−0.0005 (4)
O1A	0.0722 (7)	0.0374 (5)	0.0327 (4)	−0.0164 (5)	0.0145 (4)	−0.0051 (4)
O2A	0.0790 (8)	0.0651 (7)	0.0327 (5)	−0.0309 (6)	0.0065 (5)	0.0102 (4)
O3A	0.1449 (14)	0.0517 (7)	0.0478 (6)	−0.0264 (8)	0.0363 (8)	−0.0119 (5)
N1B	0.0575 (7)	0.0274 (5)	0.0303 (5)	−0.0147 (4)	0.0009 (4)	0.0010 (4)
N2B	0.1519 (17)	0.0432 (7)	0.0296 (6)	−0.0406 (9)	0.0088 (7)	0.0000 (5)
N3B	0.1589 (18)	0.0499 (8)	0.0356 (6)	−0.0438 (10)	0.0088 (8)	−0.0070 (5)
N4B	0.0803 (9)	0.0377 (6)	0.0431 (6)	−0.0200 (6)	0.0017 (6)	−0.0077 (5)
C5B	0.0687 (9)	0.0298 (6)	0.0405 (6)	−0.0180 (6)	−0.0023 (6)	−0.0013 (5)
C6B	0.0438 (6)	0.0267 (5)	0.0289 (5)	−0.0113 (4)	0.0008 (4)	0.0013 (4)
C7B	0.0450 (7)	0.0286 (5)	0.0318 (5)	−0.0144 (5)	0.0004 (5)	0.0046 (4)
C8B	0.0572 (8)	0.0381 (6)	0.0300 (5)	−0.0185 (6)	0.0037 (5)	0.0017 (4)
C9B	0.0559 (8)	0.0367 (6)	0.0331 (6)	−0.0180 (6)	0.0013 (5)	−0.0025 (5)
C10B	0.0431 (6)	0.0280 (5)	0.0363 (6)	−0.0143 (5)	0.0011 (5)	0.0009 (4)
C11B	0.0460 (7)	0.0279 (5)	0.0308 (5)	−0.0138 (5)	0.0018 (5)	0.0026 (4)
N12B	0.0534 (7)	0.0324 (5)	0.0458 (6)	−0.0202 (5)	−0.0002 (5)	−0.0009 (4)
O1B	0.0746 (7)	0.0328 (4)	0.0374 (5)	−0.0252 (5)	−0.0006 (4)	0.0072 (3)
O2B	0.0948 (9)	0.0432 (5)	0.0563 (6)	−0.0344 (6)	−0.0005 (6)	−0.0126 (5)
O3B	0.1042 (10)	0.0453 (6)	0.0532 (6)	−0.0418 (6)	0.0105 (6)	0.0042 (5)

Geometric parameters (Å, º)

N1A—C5A	1.327 (2)	N1B—C5B	1.334 (2)
N1A—N2A	1.346 (2)	N1B—N2B	1.350 (2)
N1A—C6A	1.427 (2)	N1B—C6B	1.431 (2)
N2A—N3A	1.290 (2)	N2B—N3B	1.287 (2)
N3A—N4A	1.350 (2)	N3B—N4B	1.343 (2)
N4A—C5A	1.300 (2)	N4B—C5B	1.307 (2)
C5A—H5A	0.92 (2)	C5B—H5B	0.96 (2)
C6A—C11A	1.378 (2)	C6B—C11B	1.381 (2)
C6A—C7A	1.401 (2)	C6B—C7B	1.405 (2)
C7A—O1A	1.337 (1)	C7B—O1B	1.337 (1)
C7A—C8A	1.395 (2)	C7B—C8B	1.397 (2)
C8A—C9A	1.377 (2)	C8B—C9B	1.376 (2)
C8A—H8A	0.98 (2)	C8B—H8B	0.98 (2)
C9A—C10A	1.384 (2)	C9B—C10B	1.384 (2)
C9A—H9A	0.99 (2)	C9B—H9B	0.96 (2)
C10A—C11A	1.383 (2)	C10B—C11B	1.381 (2)
C10A—N12A	1.458 (2)	C10B—N12B	1.461 (2)
C11A—H11A	0.99 (2)	C11B—H11B	0.94 (2)
N12A—O3A	1.207 (2)	N12B—O3B	1.220 (2)
N12A—O2A	1.227 (2)	N12B—O2B	1.222 (2)
O1A—H1A	0.91 (3)	O1B—H1B	0.93 (2)
C5A—N1A—N2A	108.0 (1)	C5B—N1B—N2B	107.2 (1)
C5A—N1A—C6A	131.5 (1)	C5B—N1B—C6B	132.8 (1)
N2A—N1A—C6A	120.5 (1)	N2B—N1B—C6B	120.0 (1)
N3A—N2A—N1A	105.9 (1)	N3B—N2B—N1B	106.9 (1)
N2A—N3A—N4A	111.1 (1)	N2B—N3B—N4B	110.6 (1)
C5A—N4A—N3A	105.5 (1)	C5B—N4B—N3B	106.1 (1)
N4A—C5A—N1A	109.5 (1)	N4B—C5B—N1B	109.2 (1)
N4A—C5A—H5A	124 (2)	N4B—C5B—H5B	124 (1)
N1A—C5A—H5A	126 (2)	N1B—C5B—H5B	127 (1)
C11A—C6A—C7A	121.4 (1)	C11B—C6B—C7B	121.0 (1)
C11A—C6A—N1A	119.2 (1)	C11B—C6B—N1B	118.7 (1)
C7A—C6A—N1A	119.4 (1)	C7B—C6B—N1B	120.3 (1)
O1A—C7A—C8A	123.6 (1)	O1B—C7B—C8B	123.0 (1)
O1A—C7A—C6A	117.5 (1)	O1B—C7B—C6B	118.4 (1)
C8A—C7A—C6A	118.8 (1)	C8B—C7B—C6B	118.6 (1)
C9A—C8A—C7A	120.5 (1)	C9B—C8B—C7B	120.8 (1)
C9A—C8A—H8A	123 (1)	C9B—C8B—H8B	119 (1)
C7A—C8A—H8A	117 (1)	C7B—C8B—H8B	121 (1)
C8A—C9A—C10A	118.9 (1)	C8B—C9B—C10B	118.9 (1)
C8A—C9A—H9A	121 (1)	C8B—C9B—H9B	121 (1)
C10A—C9A—H9A	121 (1)	C10B—C9B—H9B	120 (1)
C11A—C10A—C9A	122.5 (1)	C11B—C10B—C9B	122.3 (1)
C11A—C10A—N12A	118.1 (1)	C11B—C10B—N12B	118.4 (1)
C9A—C10A—N12A	119.3 (1)	C9B—C10B—N12B	119.3 (1)
C6A—C11A—C10A	117.8 (1)	C6B—C11B—C10B	118.4 (1)
C6A—C11A—H11A	121 (1)	C6B—C11B—H11B	119 (1)
C10A—C11A—H11A	121 (1)	C10B—C11B—H11B	122 (1)
O3A—N12A—O2A	123.3 (1)	O3B—N12B—O2B	123.2 (1)
O3A—N12A—C10A	118.7 (1)	O3B—N12B—C10B	118.3 (1)
O2A—N12A—C10A	117.8 (1)	O2B—N12B—C10B	118.5 (1)
C7A—O1A—H1A	108 (2)	C7B—O1B—H1B	108 (1)
C5A—N1A—N2A—N3A	−0.4 (2)	C5B—N1B—N2B—N3B	−0.3 (2)
C6A—N1A—N2A—N3A	177.50 (17)	C6B—N1B—N2B—N3B	177.07 (16)
N1A—N2A—N3A—N4A	0.0 (3)	N1B—N2B—N3B—N4B	−0.2 (3)
N2A—N3A—N4A—C5A	0.3 (3)	N2B—N3B—N4B—C5B	0.6 (3)
N3A—N4A—C5A—N1A	−0.6 (2)	N3B—N4B—C5B—N1B	−0.8 (2)
N2A—N1A—C5A—N4A	0.6 (2)	N2B—N1B—C5B—N4B	0.7 (2)
C6A—N1A—C5A—N4A	−176.96 (14)	C6B—N1B—C5B—N4B	−176.21 (15)
C5A—N1A—C6A—C11A	148.61 (16)	C5B—N1B—C6B—C11B	171.40 (15)
N2A—N1A—C6A—C11A	−28.7 (2)	N2B—N1B—C6B—C11B	−5.2 (2)
C5A—N1A—C6A—C7A	−32.3 (2)	C5B—N1B—C6B—C7B	−7.3 (2)
N2A—N1A—C6A—C7A	150.32 (16)	N2B—N1B—C6B—C7B	176.15 (15)
C11A—C6A—C7A—O1A	177.62 (12)	C11B—C6B—C7B—O1B	−178.09 (12)
N1A—C6A—C7A—O1A	−1.41 (19)	N1B—C6B—C7B—O1B	0.57 (19)
C11A—C6A—C7A—C8A	−1.8 (2)	C11B—C6B—C7B—C8B	1.4 (2)
N1A—C6A—C7A—C8A	179.18 (12)	N1B—C6B—C7B—C8B	−179.94 (12)
O1A—C7A—C8A—C9A	−178.39 (13)	O1B—C7B—C8B—C9B	177.87 (13)
C6A—C7A—C8A—C9A	1.0 (2)	C6B—C7B—C8B—C9B	−1.6 (2)
C7A—C8A—C9A—C10A	0.4 (2)	C7B—C8B—C9B—C10B	0.6 (2)
C8A—C9A—C10A—C11A	−1.1 (2)	C8B—C9B—C10B—C11B	0.7 (2)
C8A—C9A—C10A—N12A	−178.72 (13)	C8B—C9B—C10B—N12B	−178.93 (13)
C7A—C6A—C11A—C10A	1.2 (2)	C7B—C6B—C11B—C10B	−0.2 (2)
N1A—C6A—C11A—C10A	−179.82 (12)	N1B—C6B—C11B—C10B	−178.88 (12)
C9A—C10A—C11A—C6A	0.3 (2)	C9B—C10B—C11B—C6B	−0.9 (2)
N12A—C10A—C11A—C6A	177.97 (12)	N12B—C10B—C11B—C6B	178.74 (11)
C11A—C10A—N12A—O3A	6.6 (2)	C11B—C10B—N12B—O3B	−1.9 (2)
C9A—C10A—N12A—O3A	−175.66 (16)	C9B—C10B—N12B—O3B	177.69 (14)
C11A—C10A—N12A—O2A	−171.25 (13)	C11B—C10B—N12B—O2B	177.92 (13)
C9A—C10A—N12A—O2A	6.5 (2)	C9B—C10B—N12B—O2B	−2.5 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1A—H1A···N4B^i	0.91 (3)	1.78 (3)	2.665 (2)	165 (2)
O1B—H1B···N4A^ii	0.93 (2)	1.78 (2)	2.703 (2)	171 (2)
C5A—H5A···O2B^iii	0.92 (3)	2.55 (2)	3.234 (2)	131 (2)
C5B—H5B···O3B^iv	0.96 (2)	2.56 (2)	3.283 (2)	132 (1)
C8B—H8B···O3A^v	0.98 (2)	2.57 (2)	3.320 (2)	133 (1)
C8B—H8B···N3A^ii	0.98 (2)	2.56 (2)	3.465 (2)	153 (1)
C9A—H9A···N2B^vi	0.98 (2)	2.56 (2)	3.540 (2)	176 (2)
C9B—H9B···O2A^v	0.96 (2)	2.58 (2)	3.417 (2)	145 (2)
C11B—H11B···O2A^vi	0.94 (2)	2.53 (2)	3.191 (2)	128 (1)

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