(E)-N'-(3-Bromo-5-chloro-2-hy-droxy-benzyl-idene)nicotinohydrazide.

There are two independent mol-ecules in the asymmetric unit of the title compound, C(13)H(9)BrClN(3)O(2), in which the dihedral angles between the benzene and pyridine rings are 8.23 (9)° and 52.84 (12)°. Both the mol-ecules exist in an E configuration with respect to the C=N double bond. The two mol-ecules in the asymmetric unit are linked via weak C-H⋯O hydrogen bonds. In both the mol-ecules, an intra-molecular O-H⋯N hydrogen bond generate an S(6) graph-set motif. In the crystal, inter-molecular N-H⋯O and C-H⋯O hydrogen bonds generate bifurcated R(1) (2)(7) ring motifs. The crystal packing is further stabilized by weak inter-molecular N-H⋯O, N-H⋯N, C-H⋯O and π-π [centroid-centroid distance 3.615 (2) Å] inter-actions.

Related literature

For related structures, see: Naveenkumar et al. (2010 ▶); Su et al. (2010 ▶); Tecer et al. (2010 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C13H9BrClN3O2

M = 354.59

Monoclinic,

a = 18.2217 (5) Å

b = 7.4666 (2) Å

c = 23.6916 (5) Å

β = 122.685 (1)°

V = 2712.93 (12) Å3

Z = 8

Mo Kα radiation

μ = 3.23 mm−1

T = 295 K

0.30 × 0.24 × 0.20 mm

Data collection

Bruker APEXII diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.444, T max = 0.564

34991 measured reflections

8116 independent reflections

4715 reflections with I > 2σ(I)

R int = 0.042

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.125

S = 1.02

8116 reflections

377 parameters

4 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 1.27 e Å−3

Δρmin = −0.84 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811038268/ng5231sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811038268/ng5231Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811038268/ng5231Isup3.cml

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

C13H9BrClN3O2	F(000) = 1408
Mr = 354.59	Dx = 1.736 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7402 reflections
a = 18.2217 (5) Å	θ = 2.3–27.8°
b = 7.4666 (2) Å	µ = 3.23 mm−1
c = 23.6916 (5) Å	T = 295 K
β = 122.685 (1)°	Block, pale yellow
V = 2712.93 (12) Å3	0.30 × 0.24 × 0.20 mm
Z = 8

Bruker APEXII diffractometer	8116 independent reflections
Radiation source: fine-focus sealed tube	4715 reflections with I > 2σ(I)
graphite	Rint = 0.042
ω and φ scans	θmax = 30.4°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −25→25
Tmin = 0.444, Tmax = 0.564	k = −10→10
34991 measured reflections	l = −31→33

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.125	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.0543P)2 + 1.4342P] where P = (Fo2 + 2Fc2)/3
8116 reflections	(Δ/σ)max < 0.001
377 parameters	Δρmax = 1.27 e Å−3
4 restraints	Δρmin = −0.84 e Å−3

	x	y	z	Uiso*/Ueq
Br1	0.750800 (19)	0.43505 (5)	0.256817 (14)	0.04545 (11)
Br2	0.92847 (3)	0.37571 (8)	0.62069 (2)	0.08778 (19)
Cl1	0.97541 (6)	0.57738 (16)	0.17505 (5)	0.0727 (3)
Cl2	1.13001 (5)	0.78996 (14)	0.56676 (6)	0.0691 (3)
O1	0.41709 (16)	0.7827 (4)	−0.01578 (11)	0.0622 (7)
O2	0.62074 (13)	0.5694 (3)	0.11875 (10)	0.0427 (5)
O3	0.56100 (13)	0.6644 (3)	0.35290 (10)	0.0471 (6)
O4	0.78596 (14)	0.5308 (4)	0.49132 (11)	0.0498 (6)
N1	0.31049 (16)	1.0700 (4)	−0.22503 (12)	0.0412 (6)
N2	0.50665 (16)	0.7928 (4)	−0.05295 (12)	0.0404 (6)
N3	0.57128 (15)	0.7165 (4)	0.00520 (11)	0.0390 (6)
N4	0.34447 (16)	0.7592 (5)	0.16222 (15)	0.0613 (9)
N5	0.65084 (14)	0.7503 (4)	0.31986 (11)	0.0371 (6)
N6	0.72089 (14)	0.7123 (4)	0.38238 (11)	0.0386 (6)
C1	0.36031 (18)	0.9139 (4)	−0.12190 (14)	0.0357 (6)
C2	0.37331 (18)	0.9923 (4)	−0.16888 (14)	0.0367 (6)
H2	0.4293	0.9904	−0.1607	0.044*
C3	0.2310 (2)	1.0706 (5)	−0.23508 (16)	0.0463 (8)
H3	0.1857	1.1219	−0.2744	0.056*
C4	0.2119 (2)	1.0005 (5)	−0.19115 (17)	0.0489 (8)
H4	0.1555	1.0062	−0.2003	0.059*
C5	0.2773 (2)	0.9218 (5)	−0.13355 (16)	0.0454 (8)
H5	0.2661	0.8742	−0.1026	0.054*
C6	0.42963 (19)	0.8249 (4)	−0.05901 (14)	0.0390 (7)
C7	0.64618 (19)	0.6968 (5)	0.01529 (14)	0.0421 (7)
H7	0.6568	0.7285	−0.0176	0.051*
C8	0.71621 (18)	0.6234 (4)	0.07931 (14)	0.0384 (7)
C9	0.70035 (18)	0.5672 (4)	0.12829 (14)	0.0348 (6)
C10	0.77050 (19)	0.5086 (4)	0.18998 (14)	0.0367 (6)
C11	0.85431 (19)	0.5085 (5)	0.20395 (15)	0.0430 (7)
H11	0.9005	0.4695	0.2454	0.052*
C12	0.86859 (19)	0.5669 (5)	0.15582 (17)	0.0482 (8)
C13	0.8007 (2)	0.6208 (5)	0.09373 (17)	0.0478 (8)
H13	0.8115	0.6557	0.0612	0.057*
C14	0.49790 (16)	0.7151 (4)	0.23663 (13)	0.0323 (6)
C15	0.50623 (19)	0.6727 (4)	0.18378 (14)	0.0389 (7)
H15	0.5603	0.6442	0.1909	0.047*
C16	0.4322 (2)	0.6739 (5)	0.12011 (15)	0.0513 (9)
H16	0.4351	0.6456	0.0831	0.062*
C17	0.3545 (2)	0.7173 (6)	0.11241 (17)	0.0604 (10)
H17	0.3050	0.7176	0.0691	0.073*
C18	0.41587 (18)	0.7556 (5)	0.22332 (16)	0.0476 (8)
H18	0.4106	0.7817	0.2593	0.057*
C19	0.57123 (17)	0.7085 (4)	0.30792 (13)	0.0340 (6)
C20	0.79620 (18)	0.7645 (4)	0.39838 (15)	0.0393 (7)
H20	0.8030	0.8357	0.3693	0.047*
C21	0.87182 (18)	0.7109 (4)	0.46324 (15)	0.0390 (7)
C22	0.86279 (18)	0.5946 (4)	0.50526 (15)	0.0404 (7)
C23	0.9379 (2)	0.5408 (5)	0.56524 (15)	0.0491 (8)
C24	1.0189 (2)	0.6014 (5)	0.58363 (16)	0.0510 (9)
H24	1.0682	0.5644	0.6238	0.061*
C25	1.02624 (18)	0.7172 (5)	0.54212 (17)	0.0473 (8)
C26	0.95434 (18)	0.7721 (5)	0.48211 (16)	0.0455 (8)
H26	0.9608	0.8496	0.4543	0.055*
H2A	0.517 (2)	0.813 (5)	−0.0833 (13)	0.054 (10)*
H5A	0.655 (2)	0.804 (4)	0.2895 (12)	0.041 (9)*
H2B	0.5850 (19)	0.618 (5)	0.0836 (11)	0.063 (12)*
H4A	0.7488 (19)	0.569 (5)	0.4542 (10)	0.068 (13)*

	U11	U22	U33	U12	U13	U23
Br1	0.03930 (17)	0.0614 (2)	0.03022 (15)	−0.00234 (15)	0.01524 (12)	0.00653 (14)
Br2	0.0636 (3)	0.1316 (5)	0.0522 (2)	0.0067 (3)	0.0208 (2)	0.0320 (3)
Cl1	0.0330 (4)	0.1031 (8)	0.0796 (7)	0.0043 (5)	0.0287 (4)	0.0239 (6)
Cl2	0.0245 (4)	0.0654 (6)	0.0928 (7)	−0.0062 (4)	0.0157 (4)	−0.0170 (5)
O1	0.0541 (14)	0.102 (2)	0.0400 (13)	0.0159 (14)	0.0314 (11)	0.0236 (13)
O2	0.0291 (10)	0.0656 (15)	0.0317 (11)	0.0023 (10)	0.0152 (9)	0.0069 (11)
O3	0.0347 (11)	0.0793 (17)	0.0298 (10)	−0.0008 (11)	0.0190 (9)	0.0019 (11)
O4	0.0314 (11)	0.0760 (18)	0.0374 (12)	0.0003 (11)	0.0155 (10)	0.0022 (12)
N1	0.0359 (13)	0.0505 (16)	0.0348 (13)	0.0051 (12)	0.0176 (11)	0.0087 (12)
N2	0.0339 (13)	0.0601 (17)	0.0249 (12)	−0.0015 (12)	0.0143 (10)	0.0063 (11)
N3	0.0341 (13)	0.0509 (16)	0.0251 (11)	0.0002 (11)	0.0115 (10)	0.0051 (11)
N4	0.0264 (13)	0.094 (3)	0.0499 (17)	0.0097 (15)	0.0117 (12)	0.0140 (17)
N5	0.0219 (11)	0.0573 (17)	0.0272 (12)	0.0003 (11)	0.0100 (9)	0.0064 (11)
N6	0.0232 (11)	0.0540 (16)	0.0289 (12)	0.0022 (11)	0.0077 (9)	−0.0003 (11)
C1	0.0325 (14)	0.0427 (18)	0.0319 (14)	−0.0003 (13)	0.0174 (12)	−0.0018 (12)
C2	0.0311 (14)	0.0450 (17)	0.0352 (15)	0.0014 (13)	0.0187 (12)	0.0030 (13)
C3	0.0376 (16)	0.055 (2)	0.0391 (16)	0.0046 (15)	0.0160 (13)	0.0046 (15)
C4	0.0322 (15)	0.065 (2)	0.0488 (18)	0.0031 (15)	0.0212 (14)	0.0020 (17)
C5	0.0376 (16)	0.059 (2)	0.0467 (18)	−0.0010 (15)	0.0272 (14)	0.0026 (16)
C6	0.0361 (16)	0.050 (2)	0.0295 (14)	−0.0010 (13)	0.0171 (12)	0.0006 (13)
C7	0.0371 (16)	0.058 (2)	0.0272 (14)	−0.0037 (14)	0.0148 (12)	0.0067 (13)
C8	0.0325 (15)	0.0487 (19)	0.0306 (14)	−0.0015 (13)	0.0149 (12)	0.0043 (13)
C9	0.0294 (13)	0.0389 (16)	0.0317 (13)	−0.0021 (12)	0.0135 (11)	−0.0004 (12)
C10	0.0351 (15)	0.0404 (17)	0.0312 (14)	−0.0037 (13)	0.0156 (12)	0.0011 (12)
C11	0.0305 (15)	0.0516 (19)	0.0368 (16)	−0.0020 (14)	0.0117 (13)	0.0049 (14)
C12	0.0285 (14)	0.062 (2)	0.0513 (19)	−0.0014 (15)	0.0196 (14)	0.0073 (17)
C13	0.0375 (16)	0.065 (2)	0.0461 (18)	−0.0016 (15)	0.0260 (15)	0.0093 (16)
C14	0.0234 (12)	0.0395 (17)	0.0308 (14)	0.0019 (12)	0.0125 (11)	0.0050 (12)
C15	0.0308 (14)	0.054 (2)	0.0307 (14)	−0.0013 (13)	0.0161 (12)	0.0047 (13)
C16	0.0460 (19)	0.070 (2)	0.0288 (15)	−0.0042 (17)	0.0143 (14)	0.0041 (15)
C17	0.0329 (17)	0.087 (3)	0.0378 (18)	−0.0017 (18)	0.0037 (14)	0.0145 (18)
C18	0.0293 (15)	0.067 (2)	0.0448 (18)	0.0084 (15)	0.0190 (14)	0.0077 (16)
C19	0.0279 (13)	0.0443 (17)	0.0304 (14)	0.0024 (12)	0.0162 (11)	−0.0003 (12)
C20	0.0288 (14)	0.0459 (19)	0.0368 (15)	−0.0010 (13)	0.0135 (12)	−0.0013 (13)
C21	0.0248 (13)	0.0464 (18)	0.0373 (15)	0.0014 (13)	0.0112 (12)	−0.0089 (13)
C22	0.0283 (14)	0.054 (2)	0.0342 (15)	0.0028 (13)	0.0137 (12)	−0.0076 (13)
C23	0.0391 (17)	0.065 (2)	0.0342 (15)	0.0096 (16)	0.0142 (13)	−0.0013 (15)
C24	0.0306 (15)	0.065 (2)	0.0368 (16)	0.0095 (15)	0.0047 (13)	−0.0106 (16)
C25	0.0209 (13)	0.051 (2)	0.0547 (19)	−0.0005 (13)	0.0102 (13)	−0.0177 (17)
C26	0.0285 (14)	0.048 (2)	0.0509 (19)	−0.0029 (14)	0.0152 (14)	−0.0088 (15)

Br1—C10	1.885 (3)	C5—H5	0.9300
Br2—C23	1.876 (4)	C7—C8	1.462 (4)
Cl1—C12	1.745 (3)	C7—H7	0.9300
Cl2—C25	1.738 (3)	C8—C13	1.384 (4)
O1—C6	1.205 (4)	C8—C9	1.403 (4)
O2—C9	1.342 (3)	C9—C10	1.394 (4)
O2—H2B	0.814 (10)	C10—C11	1.377 (4)
O3—C19	1.222 (3)	C11—C12	1.370 (5)
O4—C22	1.341 (4)	C11—H11	0.9300
O4—H4A	0.818 (10)	C12—C13	1.375 (4)
N1—C2	1.331 (4)	C13—H13	0.9300
N1—C3	1.336 (4)	C14—C15	1.377 (4)
N2—C6	1.353 (4)	C14—C18	1.384 (4)
N2—N3	1.363 (3)	C14—C19	1.484 (4)
N2—H2A	0.853 (10)	C15—C16	1.378 (4)
N3—C7	1.261 (4)	C15—H15	0.9300
N4—C18	1.325 (4)	C16—C17	1.366 (5)
N4—C17	1.325 (5)	C16—H16	0.9300
N5—C19	1.356 (4)	C17—H17	0.9300
N5—N6	1.364 (3)	C18—H18	0.9300
N5—H5A	0.860 (10)	C20—C21	1.461 (4)
N6—C20	1.272 (4)	C20—H20	0.9300
C1—C5	1.385 (4)	C21—C26	1.394 (4)
C1—C2	1.386 (4)	C21—C22	1.396 (5)
C1—C6	1.492 (4)	C22—C23	1.398 (4)
C2—H2	0.9300	C23—C24	1.371 (5)
C3—C4	1.367 (5)	C24—C25	1.369 (5)
C3—H3	0.9300	C24—H24	0.9300
C4—C5	1.368 (5)	C25—C26	1.376 (4)
C4—H4	0.9300	C26—H26	0.9300
C9—O2—H2B	112 (3)	C11—C12—C13	121.2 (3)
C22—O4—H4A	107 (3)	C11—C12—Cl1	118.9 (2)
C2—N1—C3	116.4 (3)	C13—C12—Cl1	119.9 (3)
C6—N2—N3	117.5 (2)	C12—C13—C8	120.4 (3)
C6—N2—H2A	125 (2)	C12—C13—H13	119.8
N3—N2—H2A	117 (2)	C8—C13—H13	119.8
C7—N3—N2	119.8 (2)	C15—C14—C18	118.6 (3)
C18—N4—C17	116.2 (3)	C15—C14—C19	123.6 (2)
C19—N5—N6	116.5 (2)	C18—C14—C19	117.7 (3)
C19—N5—H5A	120 (2)	C14—C15—C16	118.1 (3)
N6—N5—H5A	124 (2)	C14—C15—H15	121.0
C20—N6—N5	119.1 (3)	C16—C15—H15	121.0
C5—C1—C2	117.7 (3)	C17—C16—C15	118.6 (3)
C5—C1—C6	117.6 (3)	C17—C16—H16	120.7
C2—C1—C6	124.8 (3)	C15—C16—H16	120.7
N1—C2—C1	124.0 (3)	N4—C17—C16	124.6 (3)
N1—C2—H2	118.0	N4—C17—H17	117.7
C1—C2—H2	118.0	C16—C17—H17	117.7
N1—C3—C4	124.1 (3)	N4—C18—C14	123.8 (3)
N1—C3—H3	118.0	N4—C18—H18	118.1
C4—C3—H3	118.0	C14—C18—H18	118.1
C3—C4—C5	118.7 (3)	O3—C19—N5	122.0 (3)
C3—C4—H4	120.6	O3—C19—C14	122.3 (3)
C5—C4—H4	120.6	N5—C19—C14	115.7 (2)
C4—C5—C1	119.1 (3)	N6—C20—C21	118.8 (3)
C4—C5—H5	120.4	N6—C20—H20	120.6
C1—C5—H5	120.4	C21—C20—H20	120.6
O1—C6—N2	121.7 (3)	C26—C21—C22	119.8 (3)
O1—C6—C1	121.2 (3)	C26—C21—C20	119.3 (3)
N2—C6—C1	117.1 (2)	C22—C21—C20	120.9 (3)
N3—C7—C8	119.3 (3)	O4—C22—C21	123.7 (3)
N3—C7—H7	120.3	O4—C22—C23	117.8 (3)
C8—C7—H7	120.3	C21—C22—C23	118.4 (3)
C13—C8—C9	119.3 (3)	C24—C23—C22	121.6 (3)
C13—C8—C7	119.5 (3)	C24—C23—Br2	119.0 (2)
C9—C8—C7	121.0 (3)	C22—C23—Br2	119.4 (3)
O2—C9—C10	118.4 (3)	C25—C24—C23	119.1 (3)
O2—C9—C8	122.9 (2)	C25—C24—H24	120.5
C10—C9—C8	118.6 (3)	C23—C24—H24	120.5
C11—C10—C9	121.5 (3)	C24—C25—C26	121.5 (3)
C11—C10—Br1	119.2 (2)	C24—C25—Cl2	117.8 (2)
C9—C10—Br1	119.3 (2)	C26—C25—Cl2	120.7 (3)
C12—C11—C10	119.0 (3)	C25—C26—C21	119.6 (3)
C12—C11—H11	120.5	C25—C26—H26	120.2
C10—C11—H11	120.5	C21—C26—H26	120.2
C6—N2—N3—C7	−174.5 (3)	C7—C8—C13—C12	174.4 (3)
C19—N5—N6—C20	−173.2 (3)	C18—C14—C15—C16	0.4 (5)
C3—N1—C2—C1	0.2 (5)	C19—C14—C15—C16	176.2 (3)
C5—C1—C2—N1	−1.8 (5)	C14—C15—C16—C17	0.2 (5)
C6—C1—C2—N1	179.5 (3)	C18—N4—C17—C16	−0.8 (6)
C2—N1—C3—C4	1.3 (5)	C15—C16—C17—N4	0.0 (6)
N1—C3—C4—C5	−1.1 (6)	C17—N4—C18—C14	1.4 (6)
C3—C4—C5—C1	−0.6 (5)	C15—C14—C18—N4	−1.3 (5)
C2—C1—C5—C4	2.0 (5)	C19—C14—C18—N4	−177.4 (3)
C6—C1—C5—C4	−179.2 (3)	N6—N5—C19—O3	10.6 (4)
N3—N2—C6—O1	−2.4 (5)	N6—N5—C19—C14	−167.8 (3)
N3—N2—C6—C1	178.0 (3)	C15—C14—C19—O3	−145.3 (3)
C5—C1—C6—O1	−9.7 (5)	C18—C14—C19—O3	30.6 (5)
C2—C1—C6—O1	169.1 (3)	C15—C14—C19—N5	33.1 (4)
C5—C1—C6—N2	169.9 (3)	C18—C14—C19—N5	−151.0 (3)
C2—C1—C6—N2	−11.3 (5)	N5—N6—C20—C21	−175.0 (3)
N2—N3—C7—C8	176.8 (3)	N6—C20—C21—C26	−178.0 (3)
N3—C7—C8—C13	−172.5 (3)	N6—C20—C21—C22	4.2 (5)
N3—C7—C8—C9	3.0 (5)	C26—C21—C22—O4	179.3 (3)
C13—C8—C9—O2	178.5 (3)	C20—C21—C22—O4	−2.9 (5)
C7—C8—C9—O2	3.0 (5)	C26—C21—C22—C23	−0.9 (5)
C13—C8—C9—C10	−0.6 (5)	C20—C21—C22—C23	176.9 (3)
C7—C8—C9—C10	−176.1 (3)	O4—C22—C23—C24	−179.3 (3)
O2—C9—C10—C11	−177.8 (3)	C21—C22—C23—C24	0.9 (5)
C8—C9—C10—C11	1.3 (5)	O4—C22—C23—Br2	2.9 (4)
O2—C9—C10—Br1	0.1 (4)	C21—C22—C23—Br2	−176.9 (2)
C8—C9—C10—Br1	179.3 (2)	C22—C23—C24—C25	−0.1 (5)
C9—C10—C11—C12	−0.2 (5)	Br2—C23—C24—C25	177.8 (3)
Br1—C10—C11—C12	−178.2 (3)	C23—C24—C25—C26	−0.8 (5)
C10—C11—C12—C13	−1.6 (5)	C23—C24—C25—Cl2	−179.6 (3)
C10—C11—C12—Cl1	176.8 (3)	C24—C25—C26—C21	0.9 (5)
C11—C12—C13—C8	2.4 (6)	Cl2—C25—C26—C21	179.6 (2)
Cl1—C12—C13—C8	−176.0 (3)	C22—C21—C26—C25	0.0 (5)
C9—C8—C13—C12	−1.2 (5)	C20—C21—C26—C25	−177.8 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2B···N3	0.81 (1)	1.89 (3)	2.576 (3)	142 (4)
O4—H4A···N6	0.82 (1)	1.83 (2)	2.569 (3)	149 (4)
C15—H15···O2	0.93	2.55	3.286 (4)	137
C16—H16···O1	0.93	2.41	3.185 (4)	141
N2—H2A···O3i	0.85 (1)	2.06 (1)	2.906 (3)	171 (3)
C2—H2···O3i	0.93	2.52	3.380 (4)	153
N5—H5A···N1ii	0.86 (1)	2.16 (1)	3.009 (4)	170 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2B⋯N3	0.81 (1)	1.89 (3)	2.576 (3)	142 (4)
O4—H4A⋯N6	0.82 (1)	1.83 (2)	2.569 (3)	149 (4)
C15—H15⋯O2	0.93	2.55	3.286 (4)	137
C16—H16⋯O1	0.93	2.41	3.185 (4)	141
N2—H2A⋯O3i	0.85 (1)	2.06 (1)	2.906 (3)	171 (3)
C2—H2⋯O3i	0.93	2.52	3.380 (4)	153
N5—H5A⋯N1ii	0.86 (1)	2.16 (1)	3.009 (4)	170 (3)

Symmetry codes: (i) ; (ii) .