N'-(5-Chloro-2-hydroxy-benzyl-idene)nicotinohydrazide.

There are two independent Schiff base mol-ecules in the asymmetric unit of the title compound, C(13)H(10)ClN(3)O(2). The dihedral angles between the benzene and pyridine rings are 12.8 (2) and 1.9 (2)° in the two mol-ecules. Intra-molecular O-H⋯N hydrogen bonds are observed. Mol-ecules are linked into centrosymmetric R(4) (4)(26) motifs by N-H⋯O and N-H⋯N inter-actions.

Related literature

For the biological properties of Schiff base compounds, see: Jeewoth et al. (1999 ▶); Ren et al. (2002 ▶); Eltayeb et al. (2008 ▶); Sinha et al. (2008 ▶). For metal complexes of Schiff base compounds, see: Shivakumar et al. (2008 ▶); Prabhakaran et al. (2006 ▶); Dhar et al. (2005 ▶). For related structures, see: Cui et al. (2007 ▶); Jing et al. (2007 ▶); Ma et al. (2008 ▶); Salhin et al. (2007 ▶); Lin et al. (2007 ▶); Alhadi et al. (2008 ▶); Xue et al. (2008 ▶); Wang et al. (2008 ▶); Lu (2008 ▶); Diao et al. (2008 ▶); Qiu (2009 ▶); Mohd Lair et al. (2009a ▶,b ▶). For reference structural data, see: Allen et al. (1987 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C13H10ClN3O2

M = 275.69

Monoclinic,

a = 9.792 (2) Å

b = 23.358 (3) Å

c = 10.926 (2) Å

β = 96.848 (2)°

V = 2481.2 (8) Å3

Z = 8

Mo Kα radiation

μ = 0.31 mm−1

T = 298 K

0.30 × 0.30 × 0.27 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.913, T max = 0.921

14387 measured reflections

5342 independent reflections

3193 reflections with I > 2σ(I)

R int = 0.042

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.115

S = 1.01

5342 reflections

351 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.22 e Å−3

Δρmin = −0.24 e Å−3

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); 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: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809020819/bx2215sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809020819/bx2215Isup2.hkl

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

C13H10ClN3O2	F(000) = 1136
Mr = 275.69	Dx = 1.476 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2236 reflections
a = 9.792 (2) Å	θ = 2.6–24.5°
b = 23.358 (3) Å	µ = 0.31 mm−1
c = 10.926 (2) Å	T = 298 K
β = 96.848 (2)°	Block, yellow
V = 2481.2 (8) Å3	0.30 × 0.30 × 0.27 mm
Z = 8

Bruker SMART CCD area-detector diffractometer	5342 independent reflections
Radiation source: fine-focus sealed tube	3193 reflections with I > 2σ(I)
graphite	Rint = 0.042
ω scans	θmax = 27.0°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
Tmin = 0.913, Tmax = 0.921	k = −29→27
14387 measured reflections	l = −12→13

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) = 0.115	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ2(Fo2) + (0.0466P)2] where P = (Fo2 + 2Fc2)/3
5342 reflections	(Δ/σ)max < 0.001
351 parameters	Δρmax = 0.22 e Å−3
2 restraints	Δρmin = −0.24 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
Cl1	−0.31666 (7)	0.15824 (3)	0.49570 (7)	0.0648 (2)
Cl2	0.67723 (7)	−0.10226 (3)	0.57393 (6)	0.0648 (2)
N1	0.28860 (19)	0.22587 (8)	0.70899 (16)	0.0414 (5)
N2	0.4128 (2)	0.20261 (8)	0.75424 (18)	0.0421 (5)
N3	0.7948 (2)	0.13722 (8)	0.92250 (17)	0.0438 (5)
N4	0.29718 (18)	0.00154 (8)	0.94498 (16)	0.0387 (4)
N5	0.2156 (2)	−0.01091 (8)	1.03441 (16)	0.0402 (5)
N6	−0.0434 (2)	−0.04219 (10)	1.3111 (2)	0.0659 (6)
O1	0.13564 (17)	0.31528 (6)	0.65672 (16)	0.0520 (4)
H1	0.2075	0.2981	0.6784	0.078*
O2	0.50725 (19)	0.29034 (7)	0.76057 (19)	0.0755 (6)
O3	0.39503 (17)	0.07872 (6)	0.81707 (15)	0.0486 (4)
H3	0.3484	0.0658	0.8682	0.073*
O4	0.17570 (18)	0.08396 (7)	1.05029 (15)	0.0598 (5)
C1	0.0545 (2)	0.21766 (9)	0.63088 (19)	0.0368 (5)
C2	0.0344 (2)	0.27712 (9)	0.62187 (19)	0.0394 (5)
C3	−0.0937 (3)	0.29868 (10)	0.5765 (2)	0.0496 (6)
H3A	−0.1072	0.3381	0.5715	0.059*
C4	−0.2008 (3)	0.26227 (11)	0.5390 (2)	0.0504 (6)
H4	−0.2865	0.2770	0.5088	0.060*
C5	−0.1810 (2)	0.20380 (10)	0.5461 (2)	0.0438 (6)
C6	−0.0555 (2)	0.18151 (10)	0.59222 (19)	0.0415 (6)
H6	−0.0439	0.1420	0.5977	0.050*
C7	0.1862 (2)	0.19285 (10)	0.6792 (2)	0.0411 (6)
H7	0.1957	0.1534	0.6882	0.049*
C8	0.5195 (2)	0.23961 (10)	0.7816 (2)	0.0444 (6)
C9	0.6530 (2)	0.21501 (9)	0.83757 (19)	0.0359 (5)
C10	0.7653 (3)	0.25086 (10)	0.8548 (2)	0.0483 (6)
H10	0.7567	0.2890	0.8304	0.058*
C11	0.8900 (3)	0.23037 (11)	0.9080 (2)	0.0585 (7)
H11	0.9658	0.2545	0.9224	0.070*
C12	0.9001 (3)	0.17355 (11)	0.9395 (2)	0.0509 (6)
H12	0.9849	0.1597	0.9746	0.061*
C13	0.6739 (2)	0.15881 (9)	0.8743 (2)	0.0425 (6)
H13	0.5985	0.1343	0.8649	0.051*
C14	0.4402 (2)	−0.02227 (9)	0.79497 (18)	0.0357 (5)
C15	0.4588 (2)	0.03497 (9)	0.7643 (2)	0.0380 (5)
C16	0.5456 (2)	0.04896 (10)	0.6773 (2)	0.0476 (6)
H16	0.5579	0.0872	0.6572	0.057*
C17	0.6134 (2)	0.00709 (10)	0.6205 (2)	0.0464 (6)
H17	0.6724	0.0169	0.5632	0.056*
C18	0.5936 (2)	−0.04957 (10)	0.6489 (2)	0.0446 (6)
C19	0.5080 (2)	−0.06441 (9)	0.7344 (2)	0.0414 (6)
H19	0.4951	−0.1028	0.7523	0.050*
C20	0.3537 (2)	−0.03840 (9)	0.88893 (19)	0.0395 (5)
H20	0.3400	−0.0767	0.9076	0.047*
C21	0.1567 (2)	0.03509 (10)	1.0846 (2)	0.0419 (6)
C22	0.0660 (2)	0.02299 (9)	1.18211 (19)	0.0401 (5)
C23	0.0067 (3)	0.06862 (11)	1.2362 (2)	0.0538 (7)
H23	0.0236	0.1059	1.2124	0.065*
C24	−0.0774 (3)	0.05834 (13)	1.3256 (2)	0.0651 (8)
H24	−0.1193	0.0885	1.3624	0.078*
C25	−0.0986 (3)	0.00294 (14)	1.3595 (2)	0.0657 (8)
H25	−0.1554	−0.0034	1.4206	0.079*
C26	0.0382 (3)	−0.03068 (10)	1.2238 (2)	0.0542 (7)
H26	0.0790	−0.0616	1.1887	0.065*
H5	0.206 (3)	−0.0477 (5)	1.053 (2)	0.080*
H2	0.411 (3)	0.1663 (5)	0.779 (2)	0.080*

	U11	U22	U33	U12	U13	U23
Cl1	0.0444 (4)	0.0649 (5)	0.0827 (5)	−0.0128 (3)	−0.0025 (4)	0.0037 (4)
Cl2	0.0697 (5)	0.0567 (4)	0.0709 (5)	0.0172 (4)	0.0197 (4)	−0.0037 (3)
N1	0.0369 (12)	0.0387 (11)	0.0479 (11)	0.0041 (9)	0.0020 (9)	0.0047 (9)
N2	0.0351 (12)	0.0342 (11)	0.0552 (12)	0.0012 (9)	−0.0016 (10)	0.0047 (9)
N3	0.0362 (12)	0.0371 (11)	0.0574 (13)	0.0001 (9)	0.0023 (10)	0.0029 (9)
N4	0.0374 (12)	0.0354 (11)	0.0432 (11)	−0.0026 (9)	0.0048 (9)	0.0047 (9)
N5	0.0422 (12)	0.0333 (11)	0.0465 (11)	0.0001 (9)	0.0116 (10)	0.0040 (9)
N6	0.0726 (17)	0.0628 (15)	0.0674 (15)	0.0088 (13)	0.0299 (13)	0.0101 (12)
O1	0.0514 (11)	0.0317 (9)	0.0697 (11)	−0.0002 (8)	−0.0060 (10)	0.0021 (8)
O2	0.0604 (13)	0.0346 (11)	0.1240 (16)	−0.0032 (9)	−0.0194 (12)	0.0196 (10)
O3	0.0549 (11)	0.0292 (9)	0.0649 (11)	−0.0015 (8)	0.0206 (9)	0.0034 (7)
O4	0.0713 (13)	0.0321 (10)	0.0788 (12)	0.0011 (9)	0.0205 (10)	0.0045 (9)
C1	0.0369 (14)	0.0353 (13)	0.0390 (13)	0.0020 (10)	0.0073 (10)	0.0041 (10)
C2	0.0432 (15)	0.0366 (13)	0.0387 (13)	−0.0007 (11)	0.0057 (11)	0.0002 (10)
C3	0.0506 (17)	0.0368 (14)	0.0600 (16)	0.0088 (12)	0.0013 (13)	0.0051 (11)
C4	0.0419 (16)	0.0554 (17)	0.0527 (16)	0.0080 (13)	0.0008 (12)	0.0060 (12)
C5	0.0358 (15)	0.0476 (15)	0.0481 (14)	−0.0051 (11)	0.0056 (11)	0.0018 (11)
C6	0.0430 (15)	0.0354 (13)	0.0467 (14)	−0.0024 (11)	0.0079 (11)	0.0033 (10)
C7	0.0426 (15)	0.0326 (13)	0.0482 (14)	0.0022 (11)	0.0052 (12)	0.0025 (10)
C8	0.0445 (16)	0.0353 (14)	0.0523 (15)	0.0002 (11)	0.0012 (12)	0.0038 (11)
C9	0.0376 (14)	0.0289 (12)	0.0410 (12)	−0.0028 (10)	0.0042 (10)	−0.0003 (9)
C10	0.0498 (17)	0.0308 (13)	0.0635 (16)	−0.0067 (11)	0.0035 (13)	0.0037 (11)
C11	0.0433 (16)	0.0477 (16)	0.0815 (19)	−0.0131 (13)	−0.0043 (14)	0.0003 (14)
C12	0.0367 (15)	0.0520 (17)	0.0625 (16)	0.0016 (12)	0.0000 (12)	0.0000 (12)
C13	0.0338 (14)	0.0358 (13)	0.0571 (15)	−0.0048 (11)	0.0027 (12)	0.0019 (11)
C14	0.0332 (13)	0.0330 (12)	0.0399 (13)	−0.0017 (10)	−0.0006 (10)	0.0050 (10)
C15	0.0335 (13)	0.0355 (13)	0.0444 (13)	−0.0027 (10)	0.0020 (11)	0.0005 (10)
C16	0.0530 (16)	0.0365 (14)	0.0542 (15)	−0.0072 (12)	0.0097 (13)	0.0051 (11)
C17	0.0454 (16)	0.0496 (15)	0.0457 (14)	−0.0044 (12)	0.0121 (12)	0.0040 (12)
C18	0.0449 (15)	0.0427 (14)	0.0455 (14)	0.0065 (11)	0.0029 (12)	0.0007 (11)
C19	0.0445 (15)	0.0330 (13)	0.0459 (13)	0.0020 (11)	0.0025 (11)	0.0062 (10)
C20	0.0417 (14)	0.0281 (12)	0.0482 (14)	−0.0016 (10)	0.0037 (11)	0.0049 (10)
C21	0.0393 (14)	0.0365 (14)	0.0484 (14)	−0.0008 (11)	−0.0004 (11)	−0.0002 (11)
C22	0.0367 (14)	0.0385 (14)	0.0439 (13)	0.0042 (10)	0.0005 (11)	−0.0027 (10)
C23	0.0542 (17)	0.0453 (15)	0.0622 (17)	0.0041 (13)	0.0073 (14)	−0.0108 (12)
C24	0.0600 (19)	0.068 (2)	0.0687 (19)	0.0135 (15)	0.0139 (15)	−0.0213 (15)
C25	0.0514 (18)	0.094 (2)	0.0538 (17)	0.0100 (17)	0.0166 (14)	−0.0020 (16)
C26	0.0606 (18)	0.0439 (16)	0.0619 (16)	0.0083 (13)	0.0230 (14)	−0.0006 (12)

Cl1—C5	1.740 (2)	C7—H7	0.9300
Cl2—C18	1.736 (2)	C8—C9	1.491 (3)
N1—C7	1.276 (3)	C9—C10	1.376 (3)
N1—N2	1.369 (2)	C9—C13	1.381 (3)
N2—C8	1.361 (3)	C10—C11	1.375 (3)
N2—H2	0.892 (10)	C10—H10	0.9300
N3—C12	1.332 (3)	C11—C12	1.372 (3)
N3—C13	1.336 (3)	C11—H11	0.9300
N4—C20	1.278 (3)	C12—H12	0.9300
N4—N5	1.365 (2)	C13—H13	0.9300
N5—C21	1.365 (3)	C14—C15	1.396 (3)
N5—H5	0.891 (10)	C14—C19	1.397 (3)
N6—C25	1.324 (3)	C14—C20	1.456 (3)
N6—C26	1.342 (3)	C15—C16	1.388 (3)
O1—C2	1.354 (3)	C16—C17	1.371 (3)
O1—H1	0.8200	C16—H16	0.9300
O2—C8	1.210 (2)	C17—C18	1.378 (3)
O3—C15	1.361 (2)	C17—H17	0.9300
O3—H3	0.8200	C18—C19	1.373 (3)
O4—C21	1.223 (2)	C19—H19	0.9300
C1—C6	1.394 (3)	C20—H20	0.9300
C1—C2	1.405 (3)	C21—C22	1.493 (3)
C1—C7	1.455 (3)	C22—C26	1.372 (3)
C2—C3	1.387 (3)	C22—C23	1.380 (3)
C3—C4	1.375 (3)	C23—C24	1.372 (3)
C3—H3A	0.9300	C23—H23	0.9300
C4—C5	1.380 (3)	C24—C25	1.369 (4)
C4—H4	0.9300	C24—H24	0.9300
C5—C6	1.374 (3)	C25—H25	0.9300
C6—H6	0.9300	C26—H26	0.9300
C7—N1—N2	119.29 (19)	N3—C12—C11	123.3 (2)
C8—N2—N1	116.92 (19)	N3—C12—H12	118.3
C8—N2—H2	125.2 (17)	C11—C12—H12	118.3
N1—N2—H2	116.2 (18)	N3—C13—C9	124.5 (2)
C12—N3—C13	116.7 (2)	N3—C13—H13	117.7
C20—N4—N5	120.75 (18)	C9—C13—H13	117.7
C21—N5—N4	115.52 (18)	C15—C14—C19	118.6 (2)
C21—N5—H5	127.1 (17)	C15—C14—C20	121.4 (2)
N4—N5—H5	117.4 (17)	C19—C14—C20	120.05 (19)
C25—N6—C26	115.5 (2)	O3—C15—C16	117.57 (19)
C2—O1—H1	109.5	O3—C15—C14	122.55 (19)
C15—O3—H3	109.5	C16—C15—C14	119.9 (2)
C6—C1—C2	118.8 (2)	C17—C16—C15	120.7 (2)
C6—C1—C7	119.2 (2)	C17—C16—H16	119.6
C2—C1—C7	122.0 (2)	C15—C16—H16	119.6
O1—C2—C3	117.5 (2)	C16—C17—C18	119.7 (2)
O1—C2—C1	122.7 (2)	C16—C17—H17	120.2
C3—C2—C1	119.8 (2)	C18—C17—H17	120.2
C4—C3—C2	120.5 (2)	C19—C18—C17	120.6 (2)
C4—C3—H3A	119.8	C19—C18—Cl2	120.18 (18)
C2—C3—H3A	119.8	C17—C18—Cl2	119.23 (18)
C3—C4—C5	119.9 (2)	C18—C19—C14	120.5 (2)
C3—C4—H4	120.1	C18—C19—H19	119.7
C5—C4—H4	120.1	C14—C19—H19	119.7
C6—C5—C4	120.6 (2)	N4—C20—C14	118.06 (19)
C6—C5—Cl1	120.01 (19)	N4—C20—H20	121.0
C4—C5—Cl1	119.37 (19)	C14—C20—H20	121.0
C5—C6—C1	120.4 (2)	O4—C21—N5	121.7 (2)
C5—C6—H6	119.8	O4—C21—C22	121.3 (2)
C1—C6—H6	119.8	N5—C21—C22	116.94 (19)
N1—C7—C1	119.2 (2)	C26—C22—C23	116.9 (2)
N1—C7—H7	120.4	C26—C22—C21	124.6 (2)
C1—C7—H7	120.4	C23—C22—C21	118.4 (2)
O2—C8—N2	121.6 (2)	C24—C23—C22	119.3 (2)
O2—C8—C9	121.2 (2)	C24—C23—H23	120.4
N2—C8—C9	117.3 (2)	C22—C23—H23	120.4
C10—C9—C13	116.8 (2)	C25—C24—C23	118.8 (2)
C10—C9—C8	117.9 (2)	C25—C24—H24	120.6
C13—C9—C8	125.3 (2)	C23—C24—H24	120.6
C11—C10—C9	120.0 (2)	N6—C25—C24	124.2 (3)
C11—C10—H10	120.0	N6—C25—H25	117.9
C9—C10—H10	120.0	C24—C25—H25	117.9
C12—C11—C10	118.5 (2)	N6—C26—C22	125.3 (2)
C12—C11—H11	120.8	N6—C26—H26	117.4
C10—C11—H11	120.8	C22—C26—H26	117.4
C7—N1—N2—C8	178.3 (2)	C8—C9—C13—N3	178.8 (2)
C20—N4—N5—C21	−177.7 (2)	C19—C14—C15—O3	178.9 (2)
C6—C1—C2—O1	−179.7 (2)	C20—C14—C15—O3	−2.0 (3)
C7—C1—C2—O1	0.3 (3)	C19—C14—C15—C16	−1.3 (3)
C6—C1—C2—C3	0.8 (3)	C20—C14—C15—C16	177.9 (2)
C7—C1—C2—C3	−179.2 (2)	O3—C15—C16—C17	179.9 (2)
O1—C2—C3—C4	179.7 (2)	C14—C15—C16—C17	0.1 (3)
C1—C2—C3—C4	−0.7 (3)	C15—C16—C17—C18	1.0 (4)
C2—C3—C4—C5	−0.2 (4)	C16—C17—C18—C19	−0.8 (4)
C3—C4—C5—C6	1.0 (3)	C16—C17—C18—Cl2	178.62 (18)
C3—C4—C5—Cl1	−178.88 (18)	C17—C18—C19—C14	−0.5 (3)
C4—C5—C6—C1	−1.0 (3)	Cl2—C18—C19—C14	−179.87 (17)
Cl1—C5—C6—C1	178.92 (16)	C15—C14—C19—C18	1.5 (3)
C2—C1—C6—C5	0.1 (3)	C20—C14—C19—C18	−177.7 (2)
C7—C1—C6—C5	−179.9 (2)	N5—N4—C20—C14	−179.66 (18)
N2—N1—C7—C1	−179.88 (18)	C15—C14—C20—N4	−1.5 (3)
C6—C1—C7—N1	176.7 (2)	C19—C14—C20—N4	177.7 (2)
C2—C1—C7—N1	−3.3 (3)	N4—N5—C21—O4	0.5 (3)
N1—N2—C8—O2	−3.9 (3)	N4—N5—C21—C22	179.61 (18)
N1—N2—C8—C9	176.60 (18)	O4—C21—C22—C26	178.9 (2)
O2—C8—C9—C10	−5.6 (3)	N5—C21—C22—C26	−0.2 (3)
N2—C8—C9—C10	173.9 (2)	O4—C21—C22—C23	−2.0 (3)
O2—C8—C9—C13	174.2 (2)	N5—C21—C22—C23	178.9 (2)
N2—C8—C9—C13	−6.3 (3)	C26—C22—C23—C24	−1.1 (4)
C13—C9—C10—C11	−0.9 (3)	C21—C22—C23—C24	179.7 (2)
C8—C9—C10—C11	178.9 (2)	C22—C23—C24—C25	0.8 (4)
C9—C10—C11—C12	2.0 (4)	C26—N6—C25—C24	0.2 (4)
C13—N3—C12—C11	−1.3 (4)	C23—C24—C25—N6	−0.4 (4)
C10—C11—C12—N3	−0.8 (4)	C25—N6—C26—C22	−0.6 (4)
C12—N3—C13—C9	2.5 (3)	C23—C22—C26—N6	1.1 (4)
C10—C9—C13—N3	−1.3 (3)	C21—C22—C26—N6	−179.8 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.88	2.594 (2)	145
O3—H3···N4	0.82	1.82	2.538 (2)	146
N5—H5···N3i	0.89 (1)	2.11 (1)	2.991 (3)	171 (2)
N2—H2···O3	0.89 (1)	2.10 (1)	2.984 (2)	173 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.88	2.594 (2)	145
O3—H3⋯N4	0.82	1.82	2.538 (2)	146
N5—H5⋯N3i	0.891 (10)	2.109 (11)	2.991 (3)	171 (2)
N2—H2⋯O3	0.892 (10)	2.097 (10)	2.984 (2)	173 (2)

Symmetry code: (i) .