Diaqua-{2,6-bis-[N-(2-pyridinylmeth-yl)-carbamo-yl]-phenolato-κO,O}zinc(II).

In the title compound, [Zn(C(20)H(17)N(4)O(3))(2)(H(2)O)(2)], the Zn(II) atom, lying on a twofold rotation axis, is six-coordinated in a distorted octa-hedral geometry by two phenolate O atoms and two carbonyl O atoms from two 2,6-bis-[(pyridin-2-ylmeth-yl)-carbamo-yl]phenolate ligands and by two water mol-ecules. A three-dimensional network is built up from an extensive array of hydrogen bonds and π-π inter-actions between the pyridyl rings, with a centroid-centroid distance of 3.666 (3) Å.

Related literature

For related literature, see: Chaudhuri et al. (2007 ▶); Goldsmith et al. (2002 ▶); Gumbley & Stewart (1984 ▶); Ingle et al. (2007 ▶); Kimura (1994 ▶); Lipscomb & Sträter (1996 ▶); Szajna-Fuller et al. (2007 ▶).

Experimental

Crystal data

[Zn(C20H17N4O3)2(H2O)2]

M = 824.18

Monoclinic,

a = 16.357 (4) Å

b = 14.723 (4) Å

c = 15.135 (4) Å

β = 91.938 (7)°

V = 3642.9 (16) Å3

Z = 4

Mo Kα radiation

μ = 0.74 mm−1

T = 293 (2) K

0.35 × 0.3 × 0.2 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.757, T max = 0.854

21455 measured reflections

4398 independent reflections

3575 reflections with I > 2σ(I)

R int = 0.061

Refinement

R[F 2 > 2σ(F 2)] = 0.060

wR(F 2) = 0.130

S = 1.11

4398 reflections

260 parameters

H-atom parameters constrained

Δρmax = 0.52 e Å−3

Δρmin = −0.42 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808016693/hy2136sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808016693/hy2136Isup2.hkl

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

[Zn(C20H17N4O3)2(H2O)2]	F000 = 1712
Mr = 824.18	Dx = 1.503 Mg m−3
Monoclinic, C2/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 4398 reflections
a = 16.357 (4) Å	θ = 1.9–28.0º
b = 14.723 (4) Å	µ = 0.74 mm−1
c = 15.135 (4) Å	T = 293 (2) K
β = 91.938 (7)º	Prism, colourless
V = 3642.9 (16) Å3	0.35 × 0.3 × 0.2 mm
Z = 4

Bruker SMART APEX CCD area-detector diffractometer	3575 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.061
T = 293(2) K	θmax = 28.0º
φ and ω scans	θmin = 1.9º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −21→21
Tmin = 0.757, Tmax = 0.854	k = −19→19
21455 measured reflections	l = −19→19
4398 independent reflections

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)] = 0.060	H-atom parameters constrained
wR(F2) = 0.130	w = 1/[σ2(Fo2) + (0.0553P)2 + 3.7977P] where P = (Fo2 + 2Fc2)/3
S = 1.11	(Δ/σ)max < 0.001
4398 reflections	Δρmax = 0.52 e Å−3
260 parameters	Δρmin = −0.42 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

Experimental. Compound (IV): To a solution of (III) (2.38 g, 10.2 mmol) in dry CH2Cl2 (5 ml) was added to a well stirred mixture of 2-(aminomethyl)-pyridine (2.60 ml, 25.5 mmol) and NEt3 (5.33 ml, 38.3 mmol) in dried CH2Cl2 (5 ml) under nitrogen atmosphere and the reaction was then left stirring overnight. Next, the solvent was removed under vacuum and the residue was purified by column chromatography on Al2O3 with 50% EtOAc:CH2Cl2 as eluent. The resulting pale yellow solid was recrystallized in diethyl ether to give a pure white solid (IV) (yield 68%, 2.68 g). m.p. 120–125 °C. 1H-NMR (400 MHz, CDCl3): δ 8.70 (s, 2H, –NH), 8.61 (d, J = 4.4 Hz, 2H, ArH), 8.20 (d, J = 8.0 Hz, 2H, ArH), 7.71 (m, 2H, PyH), 7.38 (m, 3H, ArH), 7.25 (m, 2H, ArH), 4.85 (s, 2H, –CH2–), 4.83 (s, 2H, –CH2–), 3.88 (s, 3H, –CH3). 13C-NMR (100 MHz, DMSO-d6): δ 164.90, 156.69, 156.53, 149.18, 136.81, 134.82, 127.60, 125.11, 122.45, 122.24, 63.83, 45.16.Compound (V): Anhydrous LiI (3.89 g, 28.9 mmol) was added to a well stirred solution of (IV) (0.78 g, 2.89 mmol) in anhydrous pyridine (20 ml) at room temperature. The reaction was allowed to proceed for 7 d with constant stirring. Then pyridine was removed in vacuum and the residue was dissloved in 1 M HCl (20 ml) and extracted with ethyl acetate (3 x 20 ml). The combined organic phase was dried over anhydrous Na2SO4, filtered and brought to dryness by rotary evaporation. The crude product was recrystallized in a solution of methanol and diethyl ether, giving (V) as a white solid (yield 92% ,0.95 g). m.p 100–103 °C. Analysis, calculated for C20H18N4O3: C 66.29, H 5.01, N 15.46%; found: C 66.31, H 4.99, N 15.45%. 1H-NMR (400 MHz, CDCl3): δ 8.77(s, 2H, –NH), 8.61 (d, J = 4.8 Hz, 2H, ArH), 8.11 (d, J = 7.6 Hz, 2H, ArH), 7.71 (m, 2H, ArH), 7.39 (d, J = 7.6 Hz, 2H, ArH), 7.26 (m, 2H, ArH), 7.03 (t, J = 8.0 Hz, 1H, ArH), 4.82 (s, 2H, –CH2–), 4.81 (s, 2H, –CH2–). 13C-NMR (100 MHz, CDCl3): δ 167.66, 160.59, 156.26, 149.06, 137.01, 133.28, 122.52, 122.08, 118.61, 117.94, 44.73. ESI: m/z 348.1458 [M+H+].

	x	y	z	Uiso*/Ueq
C1	0.02286 (15)	0.19100 (17)	0.05522 (17)	0.0236 (5)
C2	0.09384 (16)	0.24793 (18)	0.06360 (17)	0.0269 (6)
C3	0.14191 (17)	0.26133 (19)	−0.0097 (2)	0.0343 (6)
H3	0.1885	0.2972	−0.0036	0.041*
C4	0.12260 (19)	0.2232 (2)	−0.0905 (2)	0.0403 (7)
H4	0.156	0.2329	−0.1382	0.048*
C5	0.05325 (18)	0.1705 (2)	−0.10030 (19)	0.0368 (7)
H5	0.0395	0.1457	−0.1553	0.044*
C6	0.00339 (16)	0.15366 (17)	−0.02945 (17)	0.0264 (6)
C7	−0.06868 (17)	0.09354 (18)	−0.04851 (19)	0.0312 (6)
C8	−0.17697 (17)	0.0002 (2)	0.0089 (2)	0.0389 (7)
H8A	−0.183	−0.0314	0.0645	0.047*
H8B	−0.1619	−0.0445	−0.0347	0.047*
C9	−0.25903 (17)	0.04027 (19)	−0.01925 (18)	0.0299 (6)
C10	−0.27189 (18)	0.1306 (2)	−0.0387 (2)	0.0377 (7)
H10	−0.2288	0.1718	−0.0348	0.045*
C11	−0.3496 (2)	0.1594 (2)	−0.0642 (2)	0.0461 (8)
H11	−0.3598	0.2203	−0.0764	0.055*
C12	−0.4113 (2)	0.0968 (3)	−0.0711 (2)	0.0539 (9)
H12	−0.4638	0.1139	−0.0897	0.065*
C13	−0.3936 (2)	0.0081 (3)	−0.0498 (3)	0.0578 (10)
H13	−0.4358	−0.0343	−0.0539	0.069*
C14	0.11584 (15)	0.29456 (18)	0.14819 (19)	0.0291 (6)
C15	0.1960 (2)	0.4212 (2)	0.2162 (2)	0.0428 (8)
H15A	0.2548	0.4131	0.2219	0.051*
H15B	0.1723	0.3991	0.2701	0.051*
C16	0.17668 (18)	0.5211 (2)	0.20506 (19)	0.0352 (6)
N2	0.23880 (15)	0.57968 (17)	0.21397 (17)	0.0372 (6)
C20	0.2219 (2)	0.6684 (2)	0.2034 (2)	0.0478 (8)
H20	0.2647	0.7097	0.2104	0.057*
C19	0.1456 (3)	0.7013 (3)	0.1829 (2)	0.0544 (9)
H19	0.137	0.7633	0.1753	0.065*
C18	0.0825 (2)	0.6416 (3)	0.1738 (3)	0.0615 (10)
H18	0.0298	0.6619	0.1599	0.074*
N1	0.16417 (16)	0.36823 (17)	0.14154 (17)	0.0383 (6)
H1	0.1771	0.3851	0.0894	0.046*
C17	0.0979 (2)	0.5508 (3)	0.1857 (3)	0.0553 (9)
H17	0.0553	0.5091	0.1806	0.066*
N3	−0.11105 (14)	0.06472 (16)	0.01965 (16)	0.0339 (5)
H3A	−0.0987	0.0852	0.0716	0.041*
N4	−0.31909 (16)	−0.02078 (19)	−0.02365 (19)	0.0458 (7)
O1	−0.02465 (11)	0.17550 (13)	0.12131 (12)	0.0297 (4)
O2	0.09257 (12)	0.26946 (14)	0.22198 (13)	0.0363 (5)
O3	−0.08908 (14)	0.07239 (16)	−0.12543 (15)	0.0473 (6)
O4	0.08829 (13)	0.06216 (15)	0.24782 (15)	0.0431 (5)
Zn1	0	0.17016 (3)	0.25	0.02664 (14)
H24	0.0847	0.0211	0.2086	0.052 (11)*
H23	0.1415	0.067	0.2476	0.078 (14)*

	U11	U22	U33	U12	U13	U23
C1	0.0218 (12)	0.0203 (12)	0.0284 (13)	0.0028 (10)	−0.0027 (10)	0.0033 (10)
C2	0.0270 (13)	0.0237 (13)	0.0299 (14)	0.0008 (11)	0.0002 (11)	0.0035 (11)
C3	0.0272 (14)	0.0312 (15)	0.0447 (17)	−0.0039 (12)	0.0047 (12)	0.0051 (13)
C4	0.0400 (17)	0.0441 (18)	0.0376 (17)	0.0014 (14)	0.0120 (13)	0.0059 (14)
C5	0.0395 (16)	0.0410 (17)	0.0299 (15)	0.0054 (14)	0.0015 (12)	−0.0021 (13)
C6	0.0261 (13)	0.0243 (14)	0.0286 (13)	0.0041 (10)	−0.0012 (10)	0.0015 (10)
C7	0.0315 (14)	0.0255 (14)	0.0362 (16)	0.0068 (11)	−0.0054 (12)	−0.0068 (12)
C8	0.0300 (15)	0.0307 (16)	0.055 (2)	−0.0043 (12)	−0.0110 (13)	0.0031 (14)
C9	0.0305 (14)	0.0292 (14)	0.0296 (14)	−0.0046 (11)	−0.0042 (11)	0.0031 (11)
C10	0.0344 (16)	0.0315 (15)	0.0472 (18)	−0.0007 (13)	−0.0008 (13)	0.0027 (13)
C11	0.0454 (19)	0.0428 (19)	0.050 (2)	0.0122 (15)	−0.0002 (15)	0.0050 (15)
C12	0.0333 (17)	0.068 (2)	0.060 (2)	0.0082 (17)	−0.0099 (15)	0.0120 (19)
C13	0.0321 (17)	0.062 (2)	0.078 (3)	−0.0144 (17)	−0.0142 (17)	0.019 (2)
C14	0.0208 (13)	0.0247 (13)	0.0412 (16)	0.0002 (10)	−0.0071 (11)	0.0041 (12)
C15	0.0442 (18)	0.0369 (17)	0.0462 (19)	−0.0125 (14)	−0.0135 (14)	0.0017 (14)
C16	0.0353 (16)	0.0353 (16)	0.0346 (16)	−0.0068 (13)	−0.0049 (12)	0.0002 (12)
N2	0.0360 (13)	0.0322 (13)	0.0427 (14)	−0.0078 (11)	−0.0071 (11)	−0.0002 (11)
C20	0.059 (2)	0.0314 (16)	0.052 (2)	−0.0095 (16)	−0.0073 (16)	−0.0007 (15)
C19	0.078 (3)	0.0413 (19)	0.043 (2)	0.0131 (19)	−0.0050 (18)	−0.0011 (15)
C18	0.046 (2)	0.067 (3)	0.071 (3)	0.0168 (19)	−0.0048 (18)	−0.002 (2)
N1	0.0448 (15)	0.0336 (13)	0.0361 (14)	−0.0177 (11)	−0.0047 (11)	0.0052 (11)
C17	0.0342 (18)	0.060 (2)	0.071 (3)	−0.0095 (16)	−0.0053 (17)	−0.0001 (19)
N3	0.0292 (12)	0.0327 (13)	0.0393 (14)	−0.0066 (10)	−0.0069 (10)	−0.0016 (10)
N4	0.0349 (14)	0.0403 (15)	0.0615 (18)	−0.0121 (12)	−0.0109 (12)	0.0156 (13)
O1	0.0258 (9)	0.0377 (11)	0.0256 (9)	−0.0075 (8)	0.0001 (7)	0.0014 (8)
O2	0.0420 (12)	0.0356 (11)	0.0309 (11)	−0.0135 (9)	−0.0033 (9)	0.0007 (9)
O3	0.0514 (13)	0.0489 (14)	0.0410 (13)	−0.0034 (11)	−0.0087 (10)	−0.0180 (11)
O4	0.0323 (12)	0.0397 (12)	0.0567 (14)	0.0075 (9)	−0.0049 (10)	−0.0215 (11)
Zn1	0.0272 (2)	0.0271 (2)	0.0254 (2)	0	−0.00199 (16)	0

C1—O1	1.307 (3)	C13—H13	0.93
C1—C6	1.421 (4)	C14—O2	1.248 (3)
C1—C2	1.434 (4)	C14—N1	1.348 (3)
C2—C3	1.395 (4)	C15—N1	1.455 (4)
C2—C14	1.486 (4)	C15—C16	1.514 (4)
C3—C4	1.373 (4)	C15—H15A	0.97
C3—H3	0.93	C15—H15B	0.97
C4—C5	1.378 (4)	C16—N2	1.336 (4)
C4—H4	0.93	C16—C17	1.383 (4)
C5—C6	1.391 (4)	N2—C20	1.344 (4)
C5—H5	0.93	C20—C19	1.365 (5)
C6—C7	1.495 (4)	C20—H20	0.93
C7—O3	1.240 (3)	C19—C18	1.361 (6)
C7—N3	1.332 (4)	C19—H19	0.93
C8—N3	1.442 (4)	C18—C17	1.371 (5)
C8—C9	1.514 (4)	C18—H18	0.93
C8—H8A	0.97	N1—H1	0.86
C8—H8B	0.97	C17—H17	0.93
C9—N4	1.332 (4)	N3—H3A	0.86
C9—C10	1.377 (4)	O1—Zn1	1.9772 (18)
C10—C11	1.382 (4)	O2—Zn1	2.1572 (19)
C10—H10	0.93	O4—Zn1	2.149 (2)
C11—C12	1.368 (5)	O4—H24	0.85
C11—H11	0.93	O4—H23	0.87
C12—C13	1.374 (5)	Zn1—O1i	1.9772 (18)
C12—H12	0.93	Zn1—O4i	2.149 (2)
C13—N4	1.338 (4)	Zn1—O2i	2.1572 (19)
O1—C1—C6	120.1 (2)	C16—C15—H15A	109.3
O1—C1—C2	122.3 (2)	N1—C15—H15B	109.3
C6—C1—C2	117.5 (2)	C16—C15—H15B	109.3
C3—C2—C1	119.3 (2)	H15A—C15—H15B	108
C3—C2—C14	119.5 (2)	N2—C16—C17	121.2 (3)
C1—C2—C14	121.2 (2)	N2—C16—C15	117.5 (3)
C4—C3—C2	122.1 (3)	C17—C16—C15	121.3 (3)
C4—C3—H3	118.9	C16—N2—C20	117.6 (3)
C2—C3—H3	118.9	N2—C20—C19	123.7 (3)
C3—C4—C5	119.3 (3)	N2—C20—H20	118.2
C3—C4—H4	120.4	C19—C20—H20	118.2
C5—C4—H4	120.4	C18—C19—C20	118.6 (3)
C4—C5—C6	121.3 (3)	C18—C19—H19	120.7
C4—C5—H5	119.3	C20—C19—H19	120.7
C6—C5—H5	119.3	C19—C18—C17	118.8 (4)
C5—C6—C1	120.4 (2)	C19—C18—H18	120.6
C5—C6—C7	115.9 (2)	C17—C18—H18	120.6
C1—C6—C7	123.7 (2)	C14—N1—C15	124.6 (3)
O3—C7—N3	121.1 (3)	C14—N1—H1	117.7
O3—C7—C6	121.0 (3)	C15—N1—H1	117.7
N3—C7—C6	117.8 (2)	C18—C17—C16	120.1 (3)
N3—C8—C9	115.3 (2)	C18—C17—H17	119.9
N3—C8—H8A	108.4	C16—C17—H17	119.9
C9—C8—H8A	108.4	C7—N3—C8	122.0 (3)
N3—C8—H8B	108.4	C7—N3—H3A	119
C9—C8—H8B	108.4	C8—N3—H3A	119
H8A—C8—H8B	107.5	C9—N4—C13	117.6 (3)
N4—C9—C10	122.3 (3)	C1—O1—Zn1	130.85 (16)
N4—C9—C8	113.4 (2)	C14—O2—Zn1	127.87 (18)
C10—C9—C8	124.3 (3)	Zn1—O4—H24	121
C9—C10—C11	119.2 (3)	Zn1—O4—H23	128
C9—C10—H10	120.4	H24—O4—H23	96
C11—C10—H10	120.4	O1—Zn1—O1i	175.44 (11)
C12—C11—C10	118.9 (3)	O1—Zn1—O4i	85.97 (8)
C12—C11—H11	120.5	O1i—Zn1—O4i	97.42 (8)
C10—C11—H11	120.5	O1—Zn1—O4	97.42 (8)
C11—C12—C13	118.3 (3)	O1i—Zn1—O4	85.97 (8)
C11—C12—H12	120.8	O4i—Zn1—O4	84.55 (12)
C13—C12—H12	120.8	O1—Zn1—O2	84.29 (7)
N4—C13—C12	123.6 (3)	O1i—Zn1—O2	92.61 (8)
N4—C13—H13	118.2	O4i—Zn1—O2	168.82 (8)
C12—C13—H13	118.2	O4—Zn1—O2	91.26 (8)
O2—C14—N1	120.2 (3)	O1—Zn1—O2i	92.61 (8)
O2—C14—C2	124.2 (2)	O1i—Zn1—O2i	84.29 (7)
N1—C14—C2	115.7 (2)	O4i—Zn1—O2i	91.26 (8)
N1—C15—C16	111.5 (3)	O4—Zn1—O2i	168.82 (8)
N1—C15—H15A	109.3	O2—Zn1—O2i	94.67 (12)
O1—C1—C2—C3	179.9 (2)	C17—C16—N2—C20	0.0 (5)
C6—C1—C2—C3	−2.4 (4)	C15—C16—N2—C20	179.5 (3)
O1—C1—C2—C14	−1.7 (4)	C16—N2—C20—C19	−1.0 (5)
C6—C1—C2—C14	176.1 (2)	N2—C20—C19—C18	1.0 (6)
C1—C2—C3—C4	1.4 (4)	C20—C19—C18—C17	0.0 (6)
C14—C2—C3—C4	−177.1 (3)	O2—C14—N1—C15	2.9 (4)
C2—C3—C4—C5	0.5 (5)	C2—C14—N1—C15	−177.0 (3)
C3—C4—C5—C6	−1.3 (5)	C16—C15—N1—C14	−127.1 (3)
C4—C5—C6—C1	0.2 (4)	C19—C18—C17—C16	−1.0 (6)
C4—C5—C6—C7	−178.5 (3)	N2—C16—C17—C18	1.0 (5)
O1—C1—C6—C5	179.4 (2)	C15—C16—C17—C18	−178.5 (3)
C2—C1—C6—C5	1.6 (4)	O3—C7—N3—C8	6.7 (4)
O1—C1—C6—C7	−1.9 (4)	C6—C7—N3—C8	−174.4 (2)
C2—C1—C6—C7	−179.8 (2)	C9—C8—N3—C7	−83.3 (4)
C5—C6—C7—O3	−10.8 (4)	C10—C9—N4—C13	1.4 (5)
C1—C6—C7—O3	170.5 (3)	C8—C9—N4—C13	−178.6 (3)
C5—C6—C7—N3	170.3 (2)	C12—C13—N4—C9	−0.8 (6)
C1—C6—C7—N3	−8.4 (4)	C6—C1—O1—Zn1	151.87 (19)
N3—C8—C9—N4	−176.5 (3)	C2—C1—O1—Zn1	−30.4 (4)
N3—C8—C9—C10	3.5 (5)	N1—C14—O2—Zn1	168.55 (19)
N4—C9—C10—C11	−0.3 (5)	C2—C14—O2—Zn1	−11.5 (4)
C8—C9—C10—C11	179.7 (3)	C1—O1—Zn1—O4i	−143.2 (2)
C9—C10—C11—C12	−1.4 (5)	C1—O1—Zn1—O4	−59.2 (2)
C10—C11—C12—C13	1.9 (5)	C1—O1—Zn1—O2	31.3 (2)
C11—C12—C13—N4	−0.8 (6)	C1—O1—Zn1—O2i	125.8 (2)
C3—C2—C14—O2	−159.3 (3)	C14—O2—Zn1—O1	−9.8 (2)
C1—C2—C14—O2	22.2 (4)	C14—O2—Zn1—O1i	173.6 (2)
C3—C2—C14—N1	20.6 (4)	C14—O2—Zn1—O4i	19.8 (6)
C1—C2—C14—N1	−157.9 (2)	C14—O2—Zn1—O4	87.6 (2)
N1—C15—C16—N2	−127.8 (3)	C14—O2—Zn1—O2i	−101.9 (2)
N1—C15—C16—C17	51.7 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O1	0.86	1.93	2.623 (3)	136
N1—H1···N4ii	0.86	2.20	3.007 (4)	155
O4—H24···O3iii	0.85	1.87	2.712 (3)	174
O4—H23···N2iv	0.87	2.03	2.879 (3)	163

O1—Zn1	1.9772 (18)
O2—Zn1	2.1572 (19)
O4—Zn1	2.149 (2)

O1—Zn1—O1i	175.44 (11)
O1—Zn1—O4i	85.97 (8)
O1—Zn1—O4	97.42 (8)
O4i—Zn1—O4	84.55 (12)
O1—Zn1—O2	84.29 (7)
O4—Zn1—O2	91.26 (8)
O1—Zn1—O2i	92.61 (8)
O4—Zn1—O2i	168.82 (8)
O2—Zn1—O2i	94.67 (12)

Symmetry code: (i) .

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3A⋯O1	0.86	1.93	2.623 (3)	136
N1—H1⋯N4ii	0.86	2.20	3.007 (4)	155
O4—H24⋯O3iii	0.85	1.87	2.712 (3)	174
O4—H23⋯N2iv	0.87	2.03	2.879 (3)	163

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