(E)-N'-[4-(Dimethyl-amino)-benzyl-idene]-4-hy-droxy-benzohydrazide hemihydrate.

In the title compound, C(16)H(17)N(3)O(2)·0.5H(2)O, the two hydrazide mol-ecules are approximately planar: the dihedral angles between the two substituted benzene rings are 7.7 (2) and 4.2 (2)°. Both hydrazone mol-ecules exist in a trans geometry with respect to their methyl-idene units. In the crystal, the water mol-ecule lies between the two organic mol-ecules and makes bifurcated O-H⋯(N,O) hydrogen bonds to both of them. The hydrazide mol-ecules form N-H⋯O and O-H⋯O hydrogen bonds, resulting in a three-dimensional network.

Related literature

For the biological activity of hydrazone compounds, see: Banerjee et al. (2009 ▶). For the structures of hydrazone compounds, see: Ahmad et al. (2010 ▶); Li et al. (2010 ▶); Naveenkumar et al. (2010 ▶); Zhang (2009 ▶); Fun et al. (2008 ▶).

Experimental

Crystal data

C16H17N3O2·0.5H2O

M = 292.34

Monoclinic,

a = 6.1514 (9) Å

b = 18.098 (3) Å

c = 13.356 (2) Å

β = 95.489 (2)°

V = 1480.1 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 298 K

0.28 × 0.27 × 0.27 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.975, T max = 0.976

8336 measured reflections

3254 independent reflections

2593 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.094

S = 1.04

3254 reflections

407 parameters

6 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.13 e Å−3

Δρmin = −0.11 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); 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 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810020763/hb5475sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810020763/hb5475Isup2.hkl

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

C16H17N3O2·0.5H2O	F(000) = 620
Mr = 292.34	Dx = 1.312 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 2665 reflections
a = 6.1514 (9) Å	θ = 2.6–24.5°
b = 18.098 (3) Å	µ = 0.09 mm−1
c = 13.356 (2) Å	T = 298 K
β = 95.489 (2)°	Block, colorless
V = 1480.1 (4) Å3	0.28 × 0.27 × 0.27 mm
Z = 4

Bruker SMART CCD diffractometer	3254 independent reflections
Radiation source: fine-focus sealed tube	2593 reflections with I > 2σ(I)
graphite	Rint = 0.028
ω scans	θmax = 27.0°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −7→6
Tmin = 0.975, Tmax = 0.976	k = −23→23
8336 measured reflections	l = −9→17

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)] = 0.037	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.094	w = 1/[σ2(Fo2) + (0.0535P)2 + 0.0137P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
3254 reflections	Δρmax = 0.13 e Å−3
407 parameters	Δρmin = −0.11 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: 0.015 (2)

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.4602 (3)	0.17321 (13)	0.29539 (14)	0.0654 (6)
O2	0.0189 (3)	0.07939 (12)	0.68381 (15)	0.0651 (6)
H2B	0.1181	0.0548	0.7126	0.098*
O3	0.7089 (4)	0.48243 (11)	0.21582 (13)	0.0603 (5)
O4	0.3140 (3)	0.69296 (12)	−0.13484 (15)	0.0649 (6)
H4	0.4072	0.6910	−0.1747	0.097*
O5	0.7330 (3)	0.31729 (12)	0.2971 (2)	0.0688 (6)
N1	0.2364 (3)	0.27325 (12)	0.18320 (15)	0.0465 (5)
N2	0.1558 (4)	0.24130 (13)	0.26688 (16)	0.0486 (5)
N3	0.2760 (4)	0.48063 (14)	−0.21084 (17)	0.0611 (6)
N4	0.3944 (4)	0.43505 (13)	0.32898 (16)	0.0540 (6)
N5	0.3526 (4)	0.47696 (14)	0.24264 (17)	0.0565 (6)
N6	0.2273 (4)	0.26319 (14)	0.73893 (17)	0.0574 (6)
C1	0.2382 (5)	0.44061 (15)	−0.1264 (2)	0.0478 (6)
C2	0.3964 (4)	0.39311 (15)	−0.0790 (2)	0.0500 (6)
H2	0.5311	0.3887	−0.1047	0.060*
C3	0.3556 (4)	0.35288 (15)	0.0050 (2)	0.0496 (6)
H3	0.4637	0.3219	0.0349	0.059*
C4	0.1567 (4)	0.35769 (13)	0.04580 (19)	0.0423 (6)
C5	0.0014 (5)	0.40579 (16)	−0.0010 (2)	0.0523 (7)
H5	−0.1325	0.4106	0.0253	0.063*
C6	0.0391 (5)	0.44617 (15)	−0.0841 (2)	0.0540 (7)
H6	−0.0688	0.4777	−0.1130	0.065*
C7	0.4777 (6)	0.4754 (2)	−0.2563 (2)	0.0733 (9)
H7A	0.5724	0.5152	−0.2327	0.110*
H7B	0.4487	0.4785	−0.3281	0.110*
H7C	0.5468	0.4291	−0.2386	0.110*
C8	0.1119 (6)	0.5281 (2)	−0.2596 (3)	0.0777 (10)
H8A	−0.0102	0.4989	−0.2867	0.117*
H8B	0.1715	0.5544	−0.3131	0.117*
H8C	0.0646	0.5627	−0.2118	0.117*
C9	0.1034 (4)	0.31732 (14)	0.13410 (19)	0.0475 (6)
H9	−0.0343	0.3238	0.1560	0.057*
C10	0.2801 (4)	0.19211 (14)	0.32054 (19)	0.0446 (6)
C11	0.1976 (4)	0.16137 (13)	0.41294 (18)	0.0403 (5)
C12	0.3309 (4)	0.11208 (16)	0.4684 (2)	0.0518 (7)
H12	0.4620	0.0979	0.4449	0.062*
C13	0.2740 (5)	0.08319 (17)	0.5585 (2)	0.0537 (7)
H13	0.3663	0.0501	0.5949	0.064*
C14	0.0801 (5)	0.10396 (14)	0.59334 (19)	0.0486 (6)
C15	−0.0585 (5)	0.15106 (16)	0.5375 (2)	0.0548 (7)
H15	−0.1926	0.1634	0.5598	0.066*
C16	0.0001 (4)	0.18011 (15)	0.4486 (2)	0.0510 (6)
H16	−0.0937	0.2127	0.4120	0.061*
C17	0.2277 (4)	0.30157 (14)	0.65040 (19)	0.0442 (6)
C18	0.0467 (5)	0.34222 (16)	0.6109 (2)	0.0529 (7)
H18	−0.0778	0.3437	0.6452	0.063*
C19	0.0500 (5)	0.38022 (16)	0.5216 (2)	0.0565 (7)
H19	−0.0734	0.4064	0.4965	0.068*
C20	0.2329 (4)	0.38037 (14)	0.4682 (2)	0.0484 (6)
C21	0.4131 (4)	0.34006 (14)	0.5066 (2)	0.0485 (6)
H21	0.5370	0.3391	0.4718	0.058*
C22	0.4125 (4)	0.30143 (15)	0.5953 (2)	0.0490 (6)
H22	0.5359	0.2748	0.6193	0.059*
C23	0.0321 (5)	0.25746 (19)	0.7900 (2)	0.0673 (9)
H23A	−0.0182	0.3061	0.8051	0.101*
H23B	0.0634	0.2302	0.8514	0.101*
H23C	−0.0790	0.2323	0.7476	0.101*
C24	0.4155 (6)	0.2222 (2)	0.7789 (2)	0.0712 (9)
H24A	0.4520	0.1861	0.7304	0.107*
H24B	0.3842	0.1976	0.8395	0.107*
H24C	0.5364	0.2553	0.7933	0.107*
C25	0.2250 (5)	0.42193 (15)	0.3751 (2)	0.0546 (7)
H25	0.0908	0.4399	0.3476	0.065*
C26	0.5169 (5)	0.50093 (14)	0.19151 (19)	0.0473 (6)
C27	0.4562 (4)	0.55060 (13)	0.10541 (17)	0.0421 (6)
C28	0.2589 (4)	0.58769 (15)	0.09028 (19)	0.0503 (6)
H28	0.1542	0.5804	0.1351	0.060*
C29	0.2144 (4)	0.63495 (16)	0.0107 (2)	0.0517 (7)
H29	0.0806	0.6592	0.0021	0.062*
C30	0.3686 (4)	0.64671 (14)	−0.05740 (18)	0.0456 (6)
C31	0.5696 (4)	0.61128 (15)	−0.04239 (19)	0.0491 (6)
H31	0.6753	0.6193	−0.0865	0.059*
C32	0.6112 (4)	0.56435 (14)	0.03792 (19)	0.0462 (6)
H32	0.7464	0.5411	0.0476	0.055*
H2A	0.030 (3)	0.2603 (18)	0.284 (2)	0.080*
H5C	0.213 (2)	0.4898 (19)	0.223 (2)	0.080*
H5A	0.694 (5)	0.3625 (7)	0.297 (3)	0.080*
H5B	0.617 (3)	0.2919 (14)	0.285 (3)	0.080*

	U11	U22	U33	U12	U13	U23
O1	0.0554 (12)	0.0931 (15)	0.0510 (11)	0.0225 (11)	0.0224 (9)	0.0161 (11)
O2	0.0711 (14)	0.0726 (14)	0.0561 (12)	−0.0083 (11)	0.0306 (11)	0.0069 (10)
O3	0.0715 (14)	0.0634 (12)	0.0472 (11)	0.0164 (11)	0.0119 (10)	0.0052 (9)
O4	0.0611 (13)	0.0811 (14)	0.0558 (12)	0.0156 (11)	0.0230 (10)	0.0279 (11)
O5	0.0549 (12)	0.0606 (12)	0.0941 (16)	0.0071 (10)	0.0228 (12)	−0.0077 (12)
N1	0.0485 (13)	0.0501 (11)	0.0426 (12)	−0.0022 (10)	0.0124 (10)	0.0019 (10)
N2	0.0461 (12)	0.0555 (12)	0.0461 (12)	0.0021 (11)	0.0149 (10)	0.0063 (10)
N3	0.0613 (16)	0.0686 (15)	0.0532 (15)	−0.0010 (12)	0.0045 (12)	0.0180 (13)
N4	0.0742 (17)	0.0493 (12)	0.0392 (12)	−0.0003 (11)	0.0093 (11)	0.0065 (10)
N5	0.0670 (15)	0.0566 (13)	0.0470 (13)	0.0007 (12)	0.0109 (12)	0.0151 (11)
N6	0.0596 (15)	0.0673 (15)	0.0471 (13)	−0.0063 (12)	0.0153 (11)	0.0144 (12)
C1	0.0507 (16)	0.0488 (14)	0.0429 (14)	−0.0061 (12)	−0.0004 (12)	−0.0005 (12)
C2	0.0466 (15)	0.0570 (15)	0.0470 (15)	−0.0005 (13)	0.0070 (12)	0.0040 (13)
C3	0.0486 (15)	0.0507 (14)	0.0495 (15)	0.0032 (12)	0.0052 (13)	0.0044 (12)
C4	0.0421 (14)	0.0442 (13)	0.0407 (13)	0.0021 (11)	0.0041 (11)	0.0012 (11)
C5	0.0446 (15)	0.0592 (16)	0.0539 (16)	0.0081 (12)	0.0076 (12)	0.0011 (13)
C6	0.0537 (17)	0.0557 (16)	0.0520 (16)	0.0112 (13)	0.0017 (14)	0.0067 (13)
C7	0.081 (2)	0.082 (2)	0.0582 (19)	−0.0092 (19)	0.0156 (17)	0.0109 (17)
C8	0.083 (2)	0.080 (2)	0.068 (2)	0.0059 (19)	−0.0020 (18)	0.0280 (18)
C9	0.0431 (14)	0.0523 (14)	0.0479 (15)	0.0009 (12)	0.0084 (12)	−0.0007 (12)
C10	0.0447 (15)	0.0486 (14)	0.0416 (14)	−0.0001 (11)	0.0102 (11)	−0.0040 (11)
C11	0.0405 (13)	0.0415 (12)	0.0398 (13)	0.0002 (10)	0.0073 (11)	−0.0042 (10)
C12	0.0474 (15)	0.0624 (16)	0.0477 (15)	0.0042 (13)	0.0155 (12)	−0.0019 (13)
C13	0.0568 (17)	0.0601 (16)	0.0460 (14)	0.0065 (13)	0.0135 (13)	0.0075 (13)
C14	0.0553 (16)	0.0485 (14)	0.0440 (14)	−0.0101 (13)	0.0154 (12)	−0.0038 (12)
C15	0.0459 (15)	0.0631 (17)	0.0582 (17)	−0.0015 (14)	0.0196 (13)	−0.0019 (14)
C16	0.0466 (15)	0.0539 (15)	0.0540 (15)	−0.0003 (12)	0.0116 (12)	−0.0015 (13)
C17	0.0456 (14)	0.0443 (12)	0.0429 (14)	−0.0077 (11)	0.0054 (11)	0.0036 (11)
C18	0.0466 (16)	0.0582 (16)	0.0561 (16)	−0.0023 (13)	0.0165 (13)	0.0041 (14)
C19	0.0514 (17)	0.0561 (16)	0.0626 (18)	0.0050 (13)	0.0087 (14)	0.0123 (14)
C20	0.0573 (17)	0.0447 (13)	0.0442 (15)	−0.0021 (12)	0.0103 (13)	0.0045 (12)
C21	0.0513 (16)	0.0502 (14)	0.0463 (14)	−0.0049 (12)	0.0165 (12)	0.0013 (12)
C22	0.0466 (15)	0.0527 (14)	0.0485 (15)	0.0020 (12)	0.0095 (12)	0.0061 (12)
C23	0.075 (2)	0.075 (2)	0.0553 (17)	−0.0181 (17)	0.0228 (16)	0.0084 (16)
C24	0.086 (2)	0.074 (2)	0.0537 (18)	0.0081 (18)	0.0090 (17)	0.0218 (16)
C25	0.0645 (19)	0.0485 (15)	0.0511 (17)	0.0020 (13)	0.0079 (14)	0.0081 (13)
C26	0.0670 (19)	0.0406 (13)	0.0351 (13)	0.0054 (12)	0.0090 (13)	−0.0043 (11)
C27	0.0557 (15)	0.0371 (12)	0.0349 (12)	0.0009 (11)	0.0109 (11)	−0.0040 (10)
C28	0.0543 (16)	0.0564 (15)	0.0431 (14)	−0.0005 (13)	0.0198 (12)	0.0027 (12)
C29	0.0468 (15)	0.0615 (16)	0.0490 (16)	0.0078 (12)	0.0165 (12)	0.0070 (13)
C30	0.0527 (15)	0.0495 (14)	0.0368 (13)	0.0015 (12)	0.0158 (11)	0.0041 (11)
C31	0.0488 (15)	0.0559 (15)	0.0453 (15)	0.0045 (12)	0.0191 (12)	0.0020 (12)
C32	0.0505 (16)	0.0465 (14)	0.0428 (14)	0.0080 (11)	0.0103 (12)	0.0010 (11)

O1—C10	1.236 (3)	C10—C11	1.487 (3)
O2—C14	1.373 (3)	C11—C12	1.379 (4)
O2—H2B	0.8200	C11—C16	1.388 (3)
O3—C26	1.240 (3)	C12—C13	1.387 (4)
O4—C30	1.348 (3)	C12—H12	0.9300
O4—H4	0.8200	C13—C14	1.374 (4)
O5—H5A	0.852 (10)	C13—H13	0.9300
O5—H5B	0.853 (10)	C14—C15	1.374 (4)
N1—C9	1.278 (3)	C15—C16	1.378 (4)
N1—N2	1.391 (3)	C15—H15	0.9300
N2—C10	1.337 (3)	C16—H16	0.9300
N2—H2A	0.896 (10)	C17—C18	1.396 (4)
N3—C1	1.379 (3)	C17—C22	1.412 (3)
N3—C8	1.434 (4)	C18—C19	1.379 (4)
N3—C7	1.436 (4)	C18—H18	0.9300
N4—C25	1.283 (4)	C19—C20	1.389 (4)
N4—N5	1.384 (3)	C19—H19	0.9300
N5—C26	1.345 (3)	C20—C21	1.384 (4)
N5—H5C	0.903 (10)	C20—C25	1.449 (4)
N6—C17	1.371 (3)	C21—C22	1.375 (4)
N6—C24	1.435 (4)	C21—H21	0.9300
N6—C23	1.441 (3)	C22—H22	0.9300
C1—C6	1.400 (4)	C23—H23A	0.9600
C1—C2	1.403 (4)	C23—H23B	0.9600
C2—C3	1.380 (4)	C23—H23C	0.9600
C2—H2	0.9300	C24—H24A	0.9600
C3—C4	1.389 (4)	C24—H24B	0.9600
C3—H3	0.9300	C24—H24C	0.9600
C4—C5	1.395 (4)	C25—H25	0.9300
C4—C9	1.451 (4)	C26—C27	1.479 (4)
C5—C6	1.368 (4)	C27—C28	1.385 (4)
C5—H5	0.9300	C27—C32	1.396 (3)
C6—H6	0.9300	C28—C29	1.372 (4)
C7—H7A	0.9600	C28—H28	0.9300
C7—H7B	0.9600	C29—C30	1.391 (3)
C7—H7C	0.9600	C29—H29	0.9300
C8—H8A	0.9600	C30—C31	1.390 (4)
C8—H8B	0.9600	C31—C32	1.373 (4)
C8—H8C	0.9600	C31—H31	0.9300
C9—H9	0.9300	C32—H32	0.9300
C14—O2—H2B	109.5	O2—C14—C15	118.1 (2)
C30—O4—H4	109.5	C13—C14—C15	120.0 (2)
H5A—O5—H5B	107 (2)	C14—C15—C16	120.3 (3)
C9—N1—N2	114.3 (2)	C14—C15—H15	119.9
C10—N2—N1	118.5 (2)	C16—C15—H15	119.9
C10—N2—H2A	126 (2)	C15—C16—C11	120.8 (3)
N1—N2—H2A	115 (2)	C15—C16—H16	119.6
C1—N3—C8	121.3 (3)	C11—C16—H16	119.6
C1—N3—C7	122.1 (3)	N6—C17—C18	121.7 (2)
C8—N3—C7	116.5 (3)	N6—C17—C22	121.1 (2)
C25—N4—N5	114.0 (2)	C18—C17—C22	117.2 (2)
C26—N5—N4	120.7 (2)	C19—C18—C17	120.8 (2)
C26—N5—H5C	120 (2)	C19—C18—H18	119.6
N4—N5—H5C	119 (2)	C17—C18—H18	119.6
C17—N6—C24	121.0 (2)	C18—C19—C20	121.7 (3)
C17—N6—C23	121.0 (2)	C18—C19—H19	119.2
C24—N6—C23	117.8 (2)	C20—C19—H19	119.2
N3—C1—C6	121.0 (3)	C21—C20—C19	117.9 (2)
N3—C1—C2	121.8 (3)	C21—C20—C25	123.5 (2)
C6—C1—C2	117.3 (2)	C19—C20—C25	118.6 (3)
C3—C2—C1	121.2 (3)	C22—C21—C20	121.3 (2)
C3—C2—H2	119.4	C22—C21—H21	119.3
C1—C2—H2	119.4	C20—C21—H21	119.3
C2—C3—C4	121.4 (2)	C21—C22—C17	121.1 (2)
C2—C3—H3	119.3	C21—C22—H22	119.5
C4—C3—H3	119.3	C17—C22—H22	119.5
C3—C4—C5	117.0 (2)	N6—C23—H23A	109.5
C3—C4—C9	124.3 (2)	N6—C23—H23B	109.5
C5—C4—C9	118.7 (2)	H23A—C23—H23B	109.5
C6—C5—C4	122.4 (3)	N6—C23—H23C	109.5
C6—C5—H5	118.8	H23A—C23—H23C	109.5
C4—C5—H5	118.8	H23B—C23—H23C	109.5
C5—C6—C1	120.8 (3)	N6—C24—H24A	109.5
C5—C6—H6	119.6	N6—C24—H24B	109.5
C1—C6—H6	119.6	H24A—C24—H24B	109.5
N3—C7—H7A	109.5	N6—C24—H24C	109.5
N3—C7—H7B	109.5	H24A—C24—H24C	109.5
H7A—C7—H7B	109.5	H24B—C24—H24C	109.5
N3—C7—H7C	109.5	N4—C25—C20	123.1 (3)
H7A—C7—H7C	109.5	N4—C25—H25	118.5
H7B—C7—H7C	109.5	C20—C25—H25	118.5
N3—C8—H8A	109.5	O3—C26—N5	121.5 (2)
N3—C8—H8B	109.5	O3—C26—C27	122.1 (2)
H8A—C8—H8B	109.5	N5—C26—C27	116.4 (2)
N3—C8—H8C	109.5	C28—C27—C32	117.6 (2)
H8A—C8—H8C	109.5	C28—C27—C26	124.1 (2)
H8B—C8—H8C	109.5	C32—C27—C26	118.2 (2)
N1—C9—C4	123.2 (2)	C29—C28—C27	121.5 (2)
N1—C9—H9	118.4	C29—C28—H28	119.2
C4—C9—H9	118.4	C27—C28—H28	119.2
O1—C10—N2	121.4 (2)	C28—C29—C30	120.3 (2)
O1—C10—C11	120.5 (2)	C28—C29—H29	119.9
N2—C10—C11	118.1 (2)	C30—C29—H29	119.9
C12—C11—C16	117.9 (2)	O4—C30—C31	123.4 (2)
C12—C11—C10	117.1 (2)	O4—C30—C29	117.5 (2)
C16—C11—C10	124.9 (2)	C31—C30—C29	119.2 (2)
C11—C12—C13	121.6 (3)	C32—C31—C30	119.7 (2)
C11—C12—H12	119.2	C32—C31—H31	120.2
C13—C12—H12	119.2	C30—C31—H31	120.2
C14—C13—C12	119.3 (3)	C31—C32—C27	121.8 (2)
C14—C13—H13	120.3	C31—C32—H32	119.1
C12—C13—H13	120.3	C27—C32—H32	119.1
O2—C14—C13	122.0 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N5—H5C···O2i	0.90 (1)	2.56 (3)	3.171 (3)	125 (3)
N2—H2A···O5ii	0.90 (1)	2.12 (1)	3.003 (3)	168 (3)
O4—H4···O1iii	0.82	1.90	2.688 (2)	160
O2—H2B···O3iv	0.82	1.89	2.693 (3)	166
O5—H5A···O3	0.85 (1)	2.43 (2)	3.178 (3)	146 (3)
O5—H5A···N4	0.85 (1)	2.34 (2)	3.038 (3)	140 (3)
O5—H5B···O1	0.85 (1)	2.36 (2)	3.100 (3)	145 (3)
O5—H5B···N1	0.85 (1)	2.61 (2)	3.375 (3)	150 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N5—H5C⋯O2i	0.90 (1)	2.56 (3)	3.171 (3)	125 (3)
N2—H2A⋯O5ii	0.90 (1)	2.12 (1)	3.003 (3)	168 (3)
O4—H4⋯O1iii	0.82	1.90	2.688 (2)	160
O2—H2B⋯O3iv	0.82	1.89	2.693 (3)	166
O5—H5A⋯O3	0.85 (1)	2.43 (2)	3.178 (3)	146 (3)
O5—H5A⋯N4	0.85 (1)	2.34 (2)	3.038 (3)	140 (3)
O5—H5B⋯O1	0.85 (1)	2.36 (2)	3.100 (3)	145 (3)
O5—H5B⋯N1	0.85 (1)	2.61 (2)	3.375 (3)	150 (3)

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