N'-(3,5-Dibromo-2-hydroxy-benzyl-idene)-3,4-methyl-enedioxy-benzohydrazide.

In the asymmetric unit of the title hydrazone compound, C(15)H(10)Br(2)N(2)O(4), there are two independent mol-ecules. In each mol-ecule, the five-membered ring adopts a flattened envelope conformation; the flap atoms are displaced by 0.114 (2) and 0.219 (2) Å from the planes of the other four atoms. In one mol-ecule the dihedral angle between the two benzene rings is 22.8 (2)°, while in the other it is 40.8 (2)°. Each mol-ecule displays an E configuration with respect to the C=N bond. In both mol-ecules, intra-molecular O-H⋯N hydrogen bonds are observed. In the crystal structure, mol-ecules are linked through inter-molecular N-H⋯O hydrogen bonds, forming chains along the a axis.

Related literature

For the biological properties of hydrazones, see: Khattab et al. (2005 ▶); Küçükgüzel et al. (2003 ▶); Cukurovali et al. (2006 ▶). For their coordination chemistry, see: Iskander et al. (2001 ▶); Bernhardt et al. (2004 ▶); Aggarwal et al. (1981 ▶); Thomas et al. (1979 ▶). For the crystal structures of other reported n class="Chemical">hydrazones, see: Fun et al. (2008 ▶); Wei et al. (2009 ▶); Khaledi et al. (2008 ▶); Yang et al. (2008 ▶). For reference structural data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C15H10Br2N2O4

M = 442.07

Triclinic,

a = 9.793 (1) Å

b = 13.188 (2) Å

c = 13.342 (2) Å

α = 76.282 (2)°

β = 78.350 (2)°

γ = 75.911 (2)°

V = 1604.5 (4) Å3

Z = 4

Mo Kα radiation

μ = 5.07 mm−1

T = 298 K

0.23 × 0.21 × 0.21 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.388, T max = 0.416 (expected range = 0.322–0.345)

9190 measured reflections

6633 independent reflections

4090 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.141

S = 0.98

6633 reflections

423 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 1.55 e Å−3

Δρmin = −0.66 e Å−3

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); data reduction: SAIn class="Chemical">NT; 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: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680902282X/wn2332sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680902282X/wn2332Isup2.hkl

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

C15H10Br2N2O4	Z = 4
Mr = 442.07	F(000) = 864
Triclinic, P1	Dx = 1.830 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.793 (1) Å	Cell parameters from 2697 reflections
b = 13.188 (2) Å	θ = 2.8–25.0°
c = 13.342 (2) Å	µ = 5.07 mm−1
α = 76.282 (2)°	T = 298 K
β = 78.350 (2)°	Block, colorless
γ = 75.911 (2)°	0.23 × 0.21 × 0.21 mm
V = 1604.5 (4) Å3

Bruker SMART CCD area-detector diffractometer	6633 independent reflections
Radiation source: fine-focus sealed tube	4090 reflections with I > 2σ(I)
graphite	Rint = 0.026
ω scans	θmax = 27.0°, θmin = 4.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
Tmin = 0.388, Tmax = 0.416	k = −16→15
9190 measured reflections	l = −17→11

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.141	H atoms treated by a mixture of independent and constrained refinement
S = 0.98	w = 1/[σ2(Fo2) + (0.0781P)2] where P = (Fo2 + 2Fc2)/3
6633 reflections	(Δ/σ)max < 0.001
423 parameters	Δρmax = 1.55 e Å−3
2 restraints	Δρmin = −0.66 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
Br1	0.88068 (7)	−0.00513 (5)	0.23288 (6)	0.0870 (3)
Br2	0.34278 (8)	0.02682 (5)	0.11846 (5)	0.0719 (2)
Br3	−0.32989 (6)	0.72142 (5)	1.11784 (4)	0.0662 (2)
Br4	0.22028 (8)	0.81059 (6)	1.05222 (5)	0.0793 (2)
O1	0.7359 (3)	0.2022 (3)	0.2943 (3)	0.0472 (8)
H1	0.6914	0.2499	0.3252	0.071*
O2	0.6613 (3)	0.4996 (2)	0.3674 (3)	0.0436 (8)
O3	0.2556 (4)	0.9420 (3)	0.4051 (3)	0.0590 (10)
O4	0.4456 (4)	0.8602 (3)	0.4941 (3)	0.0544 (9)
O5	−0.2006 (3)	0.6068 (3)	0.9410 (3)	0.0479 (8)
H5	−0.1640	0.5740	0.8939	0.072*
O6	−0.1740 (3)	0.4855 (3)	0.7024 (3)	0.0524 (9)
O7	0.1423 (4)	0.1701 (3)	0.4070 (3)	0.0612 (10)
O8	−0.0796 (3)	0.2781 (3)	0.3989 (2)	0.0488 (8)
N1	0.5281 (4)	0.3734 (3)	0.3031 (3)	0.0369 (8)
N2	0.4637 (4)	0.4735 (3)	0.3238 (3)	0.0380 (9)
N3	−0.0003 (4)	0.5372 (3)	0.8002 (3)	0.0347 (8)
N4	0.0506 (4)	0.4792 (3)	0.7230 (3)	0.0350 (8)
C1	0.5062 (5)	0.2213 (3)	0.2451 (3)	0.0380 (10)
C2	0.6449 (5)	0.1653 (3)	0.2556 (3)	0.0379 (10)
C3	0.6891 (6)	0.0677 (4)	0.2253 (4)	0.0510 (13)
C4	0.6019 (6)	0.0259 (4)	0.1848 (4)	0.0532 (13)
H4	0.6347	−0.0397	0.1644	0.064*
C5	0.4658 (6)	0.0817 (4)	0.1746 (4)	0.0469 (12)
C6	0.4184 (5)	0.1777 (4)	0.2045 (4)	0.0426 (11)
H6	0.3258	0.2147	0.1977	0.051*
C7	0.4504 (5)	0.3269 (4)	0.2715 (4)	0.0406 (11)
H7	0.3564	0.3604	0.2651	0.049*
C8	0.5382 (4)	0.5336 (3)	0.3505 (3)	0.0317 (9)
C9	0.4569 (4)	0.6426 (3)	0.3609 (3)	0.0317 (9)
C10	0.3485 (5)	0.6950 (3)	0.3049 (3)	0.0384 (10)
H10	0.3239	0.6611	0.2595	0.046*
C11	0.2739 (5)	0.7982 (4)	0.3140 (4)	0.0419 (11)
H11	0.2002	0.8332	0.2761	0.050*
C12	0.3136 (5)	0.8447 (3)	0.3803 (4)	0.0396 (10)
C13	0.4260 (5)	0.7940 (3)	0.4349 (3)	0.0358 (10)
C14	0.4984 (5)	0.6931 (4)	0.4290 (3)	0.0366 (10)
H14	0.5715	0.6590	0.4678	0.044*
C15	0.3443 (6)	0.9581 (4)	0.4691 (4)	0.0577 (14)
H15A	0.2874	0.9781	0.5326	0.069*
H15B	0.3936	1.0149	0.4326	0.069*
C16	0.0381 (5)	0.6371 (3)	0.9138 (3)	0.0367 (10)
C17	−0.1030 (5)	0.6495 (3)	0.9648 (3)	0.0366 (10)
C18	−0.1420 (5)	0.7085 (4)	1.0440 (3)	0.0440 (11)
C19	−0.0483 (6)	0.7567 (4)	1.0706 (3)	0.0521 (13)
H19	−0.0774	0.7972	1.1224	0.062*
C20	0.0896 (6)	0.7436 (4)	1.0186 (4)	0.0506 (12)
C21	0.1344 (5)	0.6834 (4)	0.9426 (3)	0.0424 (11)
H21	0.2289	0.6734	0.9103	0.051*
C22	0.0877 (5)	0.5754 (3)	0.8309 (3)	0.0364 (10)
H22	0.1831	0.5642	0.8007	0.044*
C23	−0.0460 (4)	0.4517 (3)	0.6800 (3)	0.0336 (9)
C24	0.0118 (4)	0.3775 (3)	0.6071 (3)	0.0317 (9)
C25	0.1441 (5)	0.3100 (4)	0.6128 (4)	0.0473 (12)
H25	0.1990	0.3145	0.6603	0.057*
C26	0.1955 (5)	0.2359 (4)	0.5486 (5)	0.0587 (15)
H26	0.2835	0.1896	0.5527	0.070*
C27	0.1127 (5)	0.2339 (4)	0.4800 (4)	0.0415 (11)
C28	−0.0185 (4)	0.2998 (3)	0.4727 (3)	0.0334 (9)
C29	−0.0732 (4)	0.3735 (3)	0.5354 (3)	0.0342 (9)
H29	−0.1619	0.4185	0.5307	0.041*
C30	0.0117 (6)	0.1849 (4)	0.3679 (4)	0.0559 (14)
H30A	0.0291	0.1941	0.2924	0.067*
H30B	−0.0318	0.1234	0.3967	0.067*
H2	0.377 (3)	0.505 (5)	0.305 (5)	0.080*
H4A	0.1436 (19)	0.467 (5)	0.697 (4)	0.080*

	U11	U22	U33	U12	U13	U23
Br1	0.0757 (4)	0.0627 (4)	0.1261 (6)	0.0277 (3)	−0.0345 (4)	−0.0524 (4)
Br2	0.1068 (5)	0.0619 (4)	0.0702 (4)	−0.0450 (3)	−0.0267 (3)	−0.0179 (3)
Br3	0.0642 (4)	0.0676 (4)	0.0628 (4)	−0.0100 (3)	0.0140 (3)	−0.0288 (3)
Br4	0.1044 (5)	0.0985 (5)	0.0648 (4)	−0.0527 (4)	−0.0215 (3)	−0.0338 (3)
O1	0.0423 (18)	0.040 (2)	0.066 (2)	0.0011 (15)	−0.0170 (16)	−0.0261 (16)
O2	0.0331 (17)	0.0389 (18)	0.064 (2)	−0.0039 (14)	−0.0126 (15)	−0.0191 (15)
O3	0.065 (2)	0.0368 (19)	0.082 (3)	0.0148 (17)	−0.0351 (19)	−0.0318 (18)
O4	0.063 (2)	0.045 (2)	0.065 (2)	0.0106 (17)	−0.0285 (18)	−0.0352 (17)
O5	0.0418 (17)	0.053 (2)	0.056 (2)	−0.0102 (16)	−0.0053 (15)	−0.0247 (16)
O6	0.0313 (17)	0.062 (2)	0.076 (2)	−0.0016 (15)	−0.0097 (15)	−0.0445 (19)
O7	0.052 (2)	0.059 (2)	0.088 (3)	0.0105 (17)	−0.0254 (19)	−0.053 (2)
O8	0.0481 (18)	0.051 (2)	0.056 (2)	0.0064 (15)	−0.0226 (16)	−0.0316 (16)
N1	0.040 (2)	0.0268 (19)	0.045 (2)	−0.0009 (16)	−0.0092 (16)	−0.0143 (16)
N2	0.0318 (19)	0.0283 (19)	0.059 (2)	0.0029 (15)	−0.0149 (17)	−0.0211 (17)
N3	0.0373 (19)	0.036 (2)	0.0343 (19)	−0.0067 (16)	−0.0067 (15)	−0.0141 (16)
N4	0.0303 (18)	0.038 (2)	0.042 (2)	−0.0048 (16)	−0.0051 (16)	−0.0200 (16)
C1	0.043 (3)	0.031 (2)	0.045 (3)	−0.004 (2)	−0.011 (2)	−0.0160 (19)
C2	0.047 (3)	0.030 (2)	0.039 (2)	−0.006 (2)	−0.008 (2)	−0.0133 (19)
C3	0.060 (3)	0.035 (3)	0.055 (3)	0.005 (2)	−0.012 (2)	−0.014 (2)
C4	0.077 (4)	0.032 (3)	0.055 (3)	−0.006 (3)	−0.012 (3)	−0.020 (2)
C5	0.069 (3)	0.038 (3)	0.043 (3)	−0.026 (3)	−0.012 (2)	−0.008 (2)
C6	0.047 (3)	0.037 (3)	0.047 (3)	−0.014 (2)	−0.006 (2)	−0.009 (2)
C7	0.037 (2)	0.034 (2)	0.055 (3)	−0.003 (2)	−0.012 (2)	−0.017 (2)
C8	0.028 (2)	0.032 (2)	0.037 (2)	−0.0064 (18)	−0.0020 (17)	−0.0125 (18)
C9	0.031 (2)	0.031 (2)	0.035 (2)	−0.0070 (18)	−0.0026 (17)	−0.0096 (18)
C10	0.042 (2)	0.031 (2)	0.048 (3)	−0.0060 (19)	−0.016 (2)	−0.012 (2)
C11	0.046 (3)	0.031 (2)	0.051 (3)	0.002 (2)	−0.024 (2)	−0.011 (2)
C12	0.046 (3)	0.026 (2)	0.045 (3)	0.0014 (19)	−0.008 (2)	−0.0113 (19)
C13	0.040 (2)	0.035 (2)	0.036 (2)	−0.0028 (19)	−0.0084 (19)	−0.0186 (19)
C14	0.036 (2)	0.037 (2)	0.039 (2)	−0.0025 (19)	−0.0119 (18)	−0.0128 (19)
C15	0.067 (3)	0.045 (3)	0.066 (3)	0.009 (3)	−0.023 (3)	−0.033 (3)
C16	0.047 (3)	0.032 (2)	0.035 (2)	−0.006 (2)	−0.0144 (19)	−0.0099 (18)
C17	0.041 (2)	0.031 (2)	0.038 (2)	−0.0076 (19)	−0.0064 (19)	−0.0072 (19)
C18	0.054 (3)	0.035 (3)	0.040 (3)	−0.005 (2)	−0.005 (2)	−0.006 (2)
C19	0.076 (4)	0.050 (3)	0.033 (3)	−0.013 (3)	−0.005 (2)	−0.016 (2)
C20	0.071 (3)	0.054 (3)	0.039 (3)	−0.024 (3)	−0.016 (2)	−0.015 (2)
C21	0.047 (3)	0.049 (3)	0.038 (2)	−0.017 (2)	−0.008 (2)	−0.013 (2)
C22	0.035 (2)	0.039 (3)	0.037 (2)	−0.0048 (19)	−0.0068 (18)	−0.012 (2)
C23	0.030 (2)	0.035 (2)	0.039 (2)	−0.0068 (18)	−0.0081 (18)	−0.0116 (19)
C24	0.029 (2)	0.024 (2)	0.044 (2)	−0.0033 (17)	−0.0066 (18)	−0.0111 (18)
C25	0.042 (3)	0.047 (3)	0.064 (3)	−0.003 (2)	−0.024 (2)	−0.025 (2)
C26	0.041 (3)	0.050 (3)	0.097 (4)	0.015 (2)	−0.028 (3)	−0.048 (3)
C27	0.035 (2)	0.034 (2)	0.063 (3)	−0.0030 (19)	−0.010 (2)	−0.027 (2)
C28	0.036 (2)	0.031 (2)	0.035 (2)	−0.0048 (18)	−0.0124 (18)	−0.0071 (18)
C29	0.030 (2)	0.033 (2)	0.042 (2)	−0.0013 (18)	−0.0088 (18)	−0.0134 (19)
C30	0.058 (3)	0.051 (3)	0.068 (3)	0.004 (3)	−0.021 (3)	−0.037 (3)

Br1—C3	1.899 (5)	C7—H7	0.9300
Br2—C5	1.893 (5)	C8—C9	1.488 (6)
Br3—C18	1.892 (5)	C9—C10	1.372 (6)
Br4—C20	1.895 (5)	C9—C14	1.415 (6)
O1—C2	1.347 (5)	C10—C11	1.399 (6)
O1—H1	0.8200	C10—H10	0.9300
O2—C8	1.226 (5)	C11—C12	1.348 (6)
O3—C12	1.361 (5)	C11—H11	0.9300
O3—C15	1.415 (6)	C12—C13	1.387 (6)
O4—C13	1.377 (5)	C13—C14	1.358 (6)
O4—C15	1.437 (6)	C14—H14	0.9300
O5—C17	1.343 (5)	C15—H15A	0.9700
O5—H5	0.8200	C15—H15B	0.9700
O6—C23	1.225 (5)	C16—C21	1.396 (6)
O7—C27	1.377 (5)	C16—C17	1.400 (6)
O7—C30	1.430 (6)	C16—C22	1.463 (6)
O8—C28	1.366 (5)	C17—C18	1.396 (6)
O8—C30	1.428 (5)	C18—C19	1.377 (7)
N1—C7	1.269 (6)	C19—C20	1.378 (7)
N1—N2	1.384 (5)	C19—H19	0.9300
N2—C8	1.345 (5)	C20—C21	1.372 (6)
N2—H2	0.91 (4)	C21—H21	0.9300
N3—C22	1.271 (5)	C22—H22	0.9300
N3—N4	1.370 (5)	C23—C24	1.477 (5)
N4—C23	1.357 (5)	C24—C25	1.386 (6)
N4—H4A	0.90 (3)	C24—C29	1.406 (6)
C1—C6	1.393 (6)	C25—C26	1.388 (6)
C1—C2	1.396 (6)	C25—H25	0.9300
C1—C7	1.465 (6)	C26—C27	1.348 (6)
C2—C3	1.384 (6)	C26—H26	0.9300
C3—C4	1.371 (7)	C27—C28	1.373 (6)
C4—C5	1.373 (7)	C28—C29	1.371 (6)
C4—H4	0.9300	C29—H29	0.9300
C5—C6	1.362 (6)	C30—H30A	0.9700
C6—H6	0.9300	C30—H30B	0.9700
C2—O1—H1	109.5	C9—C14—H14	121.7
C12—O3—C15	106.3 (3)	O3—C15—O4	108.3 (4)
C13—O4—C15	105.3 (3)	O3—C15—H15A	110.0
C17—O5—H5	109.5	O4—C15—H15A	110.0
C27—O7—C30	105.6 (3)	O3—C15—H15B	110.0
C28—O8—C30	105.7 (3)	O4—C15—H15B	110.0
C7—N1—N2	115.5 (3)	H15A—C15—H15B	108.4
C8—N2—N1	120.9 (3)	C21—C16—C17	119.9 (4)
C8—N2—H2	118 (4)	C21—C16—C22	118.8 (4)
N1—N2—H2	120 (4)	C17—C16—C22	121.3 (4)
C22—N3—N4	117.8 (3)	O5—C17—C18	119.3 (4)
C23—N4—N3	117.6 (3)	O5—C17—C16	122.7 (4)
C23—N4—H4A	121 (4)	C18—C17—C16	118.0 (4)
N3—N4—H4A	121 (4)	C19—C18—C17	122.3 (4)
C6—C1—C2	119.3 (4)	C19—C18—Br3	119.0 (4)
C6—C1—C7	118.2 (4)	C17—C18—Br3	118.7 (4)
C2—C1—C7	122.4 (4)	C18—C19—C20	118.4 (4)
O1—C2—C3	119.3 (4)	C18—C19—H19	120.8
O1—C2—C1	122.7 (4)	C20—C19—H19	120.8
C3—C2—C1	118.0 (4)	C21—C20—C19	121.5 (5)
C4—C3—C2	122.1 (4)	C21—C20—Br4	119.1 (4)
C4—C3—Br1	119.7 (4)	C19—C20—Br4	119.3 (4)
C2—C3—Br1	118.0 (4)	C20—C21—C16	119.9 (4)
C3—C4—C5	119.4 (4)	C20—C21—H21	120.1
C3—C4—H4	120.3	C16—C21—H21	120.1
C5—C4—H4	120.3	N3—C22—C16	119.6 (4)
C6—C5—C4	120.1 (5)	N3—C22—H22	120.2
C6—C5—Br2	119.4 (4)	C16—C22—H22	120.2
C4—C5—Br2	120.5 (4)	O6—C23—N4	121.2 (4)
C5—C6—C1	121.1 (4)	O6—C23—C24	122.4 (4)
C5—C6—H6	119.4	N4—C23—C24	116.4 (3)
C1—C6—H6	119.4	C25—C24—C29	120.9 (4)
N1—C7—C1	121.1 (4)	C25—C24—C23	120.5 (4)
N1—C7—H7	119.5	C29—C24—C23	118.5 (3)
C1—C7—H7	119.5	C24—C25—C26	120.8 (4)
O2—C8—N2	122.4 (4)	C24—C25—H25	119.6
O2—C8—C9	123.4 (4)	C26—C25—H25	119.6
N2—C8—C9	114.2 (3)	C27—C26—C25	117.3 (4)
C10—C9—C14	120.3 (4)	C27—C26—H26	121.4
C10—C9—C8	122.2 (4)	C25—C26—H26	121.4
C14—C9—C8	117.5 (4)	C26—C27—C28	123.0 (4)
C9—C10—C11	121.8 (4)	C26—C27—O7	127.8 (4)
C9—C10—H10	119.1	C28—C27—O7	109.1 (4)
C11—C10—H10	119.1	O8—C28—C29	128.4 (4)
C12—C11—C10	117.1 (4)	O8—C28—C27	110.3 (4)
C12—C11—H11	121.4	C29—C28—C27	121.3 (4)
C10—C11—H11	121.4	C28—C29—C24	116.6 (4)
C11—C12—O3	128.3 (4)	C28—C29—H29	121.7
C11—C12—C13	121.7 (4)	C24—C29—H29	121.7
O3—C12—C13	110.0 (4)	O8—C30—O7	107.0 (3)
C14—C13—O4	128.2 (4)	O8—C30—H30A	110.3
C14—C13—C12	122.4 (4)	O7—C30—H30A	110.3
O4—C13—C12	109.4 (4)	O8—C30—H30B	110.3
C13—C14—C9	116.6 (4)	O7—C30—H30B	110.3
C13—C14—H14	121.7	H30A—C30—H30B	108.6

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	2.00	2.654 (4)	137
O5—H5···N3	0.82	1.86	2.582 (4)	146
N2—H2···O6i	0.91 (4)	1.99 (3)	2.833 (5)	155 (6)
N4—H4A···O2ii	0.90 (3)	2.04 (3)	2.888 (5)	158 (6)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	2.00	2.654 (4)	137
O5—H5⋯N3	0.82	1.86	2.582 (4)	146
N2—H2⋯O6i	0.91 (4)	1.99 (3)	2.833 (5)	155 (6)
N4—H4A⋯O2ii	0.90 (3)	2.04 (3)	2.888 (5)	158 (6)

Symmetry codes: (i) ; (ii) .