4'-Amino-2,2''-dioxo-2,2'',3,3''-tetra-hydro-1H-indole-3-spiro-1'-cyclo-pent-3'-ene-2'-spiro-3''-1H-indole-3',5',5'-tricarbonitrile dihydrate.

In the title compound, C(22)H(12)N(6)O(2)·2H(2)O, the cyclo-pentene ring adopts an envelope conformation, with the spiro C atom bonded to the dicyano-substituted C atom deviating by 0.437 (2) Å from the plane of the remaining four atoms in the ring. The puckering and smallest displacement asymmetry parameters for the ring are q(2) = 0.275 (2) Å, ϕ = 212.4 (4)° and Δ(s)(C(2)) = 2.7 (2). The dihedral angle between the two indole groups is 60.1 (1)°. The structure contains inter-molecular N-H⋯O hydrogen bonds involving the indole groups and O-H⋯O and O-H⋯N hydrogen bonds involving the water mol-ecules.

Related literature

For related literature, see: Akai et al. (2004 ▶); Cremer & Pople (1975 ▶); Gallagher et al. (1985 ▶); Nagata et al. (2001 ▶); Nardelli (1983 ▶); Williams & Cox (2003 ▶); Zaveri et al. (2004 ▶).

Experimental

Crystal data

C22H12N6O2·2H2O

M = 428.41

Orthorhombic,

a = 17.1850 (16) Å

b = 8.9849 (9) Å

c = 13.3275 (13) Å

V = 2057.8 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 293 (2) K

0.25 × 0.24 × 0.20 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: none

16968 measured reflections

2551 independent reflections

2367 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.108

S = 1.06

2551 reflections

313 parameters

9 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.27 e Å−3

Δρmin = −0.14 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); 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, 2003 ▶); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808002146/bi2273sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808002146/bi2273Isup2.hkl

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

C22H12N6O2·2H2O	F000 = 888
Mr = 428.41	Dx = 1.383 Mg m−3
Orthorhombic, Pna21	Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 2386 reflections
a = 17.1850 (16) Å	θ = 2.4–28.0º
b = 8.9849 (9) Å	µ = 0.10 mm−1
c = 13.3275 (13) Å	T = 293 (2) K
V = 2057.8 (3) Å3	Block, colorless
Z = 4	0.25 × 0.24 × 0.20 mm

Bruker SMART APEX CCD diffractometer	2367 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.022
Monochromator: graphite	θmax = 28.0º
T = 293(2) K	θmin = 2.4º
ω scans	h = −22→22
Absorption correction: none	k = −11→11
16968 measured reflections	l = −17→17
2551 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)] = 0.042	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.108	w = 1/[σ2(Fo2) + (0.0751P)2 + 0.1068P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max < 0.001
2551 reflections	Δρmax = 0.27 e Å−3
313 parameters	Δρmin = −0.14 e Å−3
9 restraints	Extinction correction: none
Primary atom site location: structure-invariant direct methods

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
C1	0.19406 (12)	0.1506 (2)	0.03645 (16)	0.0341 (4)
C2	0.19661 (11)	0.0810 (2)	0.14549 (15)	0.0320 (4)
C3	0.11505 (12)	0.1206 (2)	0.19253 (16)	0.0352 (4)
C4	0.09089 (12)	0.2598 (2)	0.13339 (17)	0.0349 (4)
C5	0.13624 (13)	0.2738 (2)	0.05081 (16)	0.0354 (4)
C6	0.16280 (14)	0.0331 (2)	−0.03919 (16)	0.0414 (5)
C7	0.28704 (15)	0.0835 (3)	−0.08495 (19)	0.0452 (5)
C8	0.35505 (18)	0.0831 (4)	−0.1392 (2)	0.0614 (7)
H8A	0.3636	0.0143	−0.1902	0.074*
C9	0.41025 (19)	0.1889 (4)	−0.1150 (3)	0.0679 (8)
H9A	0.4570	0.1906	−0.1501	0.082*
C10	0.39785 (17)	0.2922 (4)	−0.0399 (3)	0.0612 (7)
H10A	0.4358	0.3629	−0.0256	0.073*
C11	0.32867 (16)	0.2907 (3)	0.0144 (2)	0.0489 (6)
H11A	0.3198	0.3607	0.0645	0.059*
C12	0.27339 (13)	0.1839 (2)	−0.00708 (16)	0.0375 (4)
C13	0.25886 (12)	0.1685 (2)	0.20696 (15)	0.0340 (4)
C14	0.29683 (12)	−0.0747 (2)	0.20308 (17)	0.0378 (4)
C15	0.34057 (15)	−0.2019 (3)	0.2170 (2)	0.0493 (6)
H15A	0.3882	−0.1992	0.2501	0.059*
C16	0.31063 (17)	−0.3336 (3)	0.1795 (2)	0.0564 (7)
H16A	0.3388	−0.4211	0.1878	0.068*
C17	0.24070 (18)	−0.3388 (3)	0.1305 (2)	0.0581 (7)
H17A	0.2221	−0.4293	0.1065	0.070*
C18	0.19709 (16)	−0.2097 (2)	0.1161 (2)	0.0489 (6)
H18A	0.1497	−0.2129	0.0824	0.059*
C19	0.22569 (13)	−0.0769 (2)	0.15289 (16)	0.0364 (4)
C20	0.12114 (15)	0.1500 (3)	0.30204 (19)	0.0449 (5)
C21	0.05602 (14)	0.0018 (3)	0.1798 (2)	0.0470 (5)
C22	0.12327 (16)	0.3857 (3)	−0.0210 (2)	0.0506 (6)
N1	0.22129 (14)	−0.0067 (2)	−0.09965 (16)	0.0486 (5)
H1	0.2189	−0.0785	−0.1422	0.058*
N2	0.31446 (11)	0.0717 (2)	0.23268 (15)	0.0413 (4)
H2	0.3564	0.0962	0.2639	0.050*
N3	0.12535 (18)	0.1713 (4)	0.38515 (19)	0.0706 (7)
N4	0.01054 (15)	−0.0884 (3)	0.1731 (3)	0.0727 (8)
N5	0.03222 (13)	0.3429 (3)	0.16605 (18)	0.0498 (5)
H5A	0.0025 (15)	0.311 (3)	0.2169 (17)	0.048 (7)*
H5B	0.011 (2)	0.417 (3)	0.130 (3)	0.070 (10)*
N6	0.1106 (2)	0.4754 (4)	−0.0785 (3)	0.0916 (11)
O1	0.09597 (11)	−0.0125 (2)	−0.04096 (16)	0.0567 (5)
O2	0.25526 (10)	0.29951 (16)	0.22853 (13)	0.0429 (4)
O3	0.05768 (12)	0.7461 (2)	0.83632 (15)	0.0540 (4)
H3A	0.073 (3)	0.830 (3)	0.858 (3)	0.107 (15)*
H3B	0.054 (4)	0.692 (4)	0.888 (2)	0.15 (2)*
O4	0.0238 (2)	0.3832 (4)	0.5501 (3)	0.0938 (9)
H4A	0.020 (4)	0.322 (6)	0.599 (4)	0.16 (3)*
H4B	0.066 (2)	0.360 (6)	0.521 (4)	0.13 (2)*

	U11	U22	U33	U12	U13	U23
C1	0.0439 (10)	0.0289 (9)	0.0294 (9)	0.0008 (8)	−0.0003 (8)	−0.0036 (7)
C2	0.0387 (9)	0.0268 (9)	0.0304 (9)	−0.0010 (7)	−0.0022 (8)	−0.0033 (7)
C3	0.0384 (9)	0.0334 (9)	0.0338 (10)	−0.0009 (8)	0.0006 (8)	0.0015 (8)
C4	0.0404 (10)	0.0319 (9)	0.0325 (9)	−0.0002 (7)	−0.0024 (8)	−0.0019 (8)
C5	0.0428 (10)	0.0329 (10)	0.0305 (9)	0.0024 (8)	−0.0017 (8)	−0.0015 (8)
C6	0.0565 (13)	0.0354 (10)	0.0324 (10)	0.0013 (9)	−0.0081 (10)	−0.0082 (8)
C7	0.0582 (13)	0.0408 (11)	0.0367 (11)	0.0131 (10)	0.0031 (10)	−0.0020 (9)
C8	0.0700 (18)	0.0639 (17)	0.0503 (15)	0.0182 (13)	0.0193 (14)	−0.0015 (13)
C9	0.0570 (16)	0.083 (2)	0.0642 (18)	0.0135 (15)	0.0240 (14)	0.0145 (17)
C10	0.0539 (15)	0.0616 (16)	0.0682 (19)	−0.0052 (12)	0.0088 (14)	0.0140 (14)
C11	0.0552 (14)	0.0411 (12)	0.0504 (14)	−0.0037 (10)	0.0070 (11)	−0.0017 (10)
C12	0.0449 (11)	0.0353 (10)	0.0321 (10)	0.0060 (8)	0.0030 (9)	0.0003 (8)
C13	0.0407 (9)	0.0341 (9)	0.0271 (9)	−0.0040 (8)	0.0010 (8)	−0.0036 (7)
C14	0.0443 (10)	0.0351 (10)	0.0340 (10)	0.0029 (8)	0.0020 (9)	−0.0012 (8)
C15	0.0517 (13)	0.0486 (13)	0.0476 (13)	0.0143 (10)	0.0002 (11)	0.0010 (11)
C16	0.0687 (16)	0.0374 (11)	0.0632 (16)	0.0167 (11)	0.0081 (13)	0.0036 (11)
C17	0.0764 (18)	0.0286 (11)	0.0692 (18)	0.0006 (11)	0.0009 (14)	−0.0073 (11)
C18	0.0586 (14)	0.0320 (10)	0.0563 (14)	−0.0015 (9)	−0.0054 (12)	−0.0061 (10)
C19	0.0443 (10)	0.0300 (9)	0.0351 (10)	0.0021 (8)	0.0006 (9)	−0.0004 (8)
C20	0.0473 (12)	0.0483 (12)	0.0392 (13)	0.0044 (10)	0.0049 (10)	0.0056 (10)
C21	0.0447 (11)	0.0433 (12)	0.0530 (14)	−0.0024 (10)	−0.0003 (11)	0.0055 (10)
C22	0.0640 (15)	0.0478 (12)	0.0400 (12)	0.0167 (11)	0.0151 (11)	0.0054 (10)
N1	0.0696 (13)	0.0394 (10)	0.0368 (10)	0.0049 (9)	−0.0004 (10)	−0.0135 (8)
N2	0.0418 (9)	0.0414 (9)	0.0406 (10)	0.0006 (7)	−0.0076 (8)	−0.0047 (8)
N3	0.0812 (18)	0.0944 (19)	0.0363 (13)	0.0063 (14)	0.0041 (11)	0.0020 (12)
N4	0.0595 (13)	0.0613 (14)	0.097 (2)	−0.0217 (12)	−0.0013 (14)	0.0057 (15)
N5	0.0509 (11)	0.0526 (12)	0.0458 (11)	0.0136 (9)	0.0108 (10)	0.0073 (9)
N6	0.121 (3)	0.084 (2)	0.0696 (18)	0.0470 (19)	0.0373 (18)	0.0380 (16)
O1	0.0578 (11)	0.0560 (10)	0.0563 (11)	−0.0089 (8)	−0.0123 (9)	−0.0163 (9)
O2	0.0552 (9)	0.0330 (7)	0.0404 (8)	−0.0026 (6)	−0.0050 (7)	−0.0110 (6)
O3	0.0606 (11)	0.0517 (9)	0.0498 (10)	0.0029 (9)	−0.0094 (9)	−0.0077 (8)
O4	0.093 (2)	0.091 (2)	0.097 (2)	0.0319 (15)	−0.0022 (16)	0.0075 (18)

C1—C5	1.500 (3)	C11—H11A	0.930
C1—C12	1.511 (3)	C13—O2	1.213 (3)
C1—C6	1.556 (3)	C13—N2	1.337 (3)
C1—C2	1.583 (3)	C14—C15	1.380 (3)
C2—C19	1.508 (3)	C14—C19	1.394 (3)
C2—C13	1.560 (3)	C14—N2	1.406 (3)
C2—C3	1.576 (3)	C15—C16	1.384 (4)
C3—C21	1.482 (3)	C15—H15A	0.930
C3—C20	1.487 (3)	C16—C17	1.369 (4)
C3—C4	1.535 (3)	C16—H16A	0.930
C4—N5	1.328 (3)	C17—C18	1.394 (4)
C4—C5	1.354 (3)	C17—H17A	0.930
C5—C22	1.406 (3)	C18—C19	1.380 (3)
C6—O1	1.220 (3)	C18—H18A	0.930
C6—N1	1.337 (3)	C20—N3	1.126 (4)
C7—C8	1.374 (4)	C21—N4	1.130 (3)
C7—C12	1.395 (3)	C22—N6	1.133 (4)
C7—N1	1.404 (3)	N1—H1	0.860
C8—C9	1.381 (5)	N2—H2	0.860
C8—H8A	0.930	N5—H5A	0.90 (1)
C9—C10	1.382 (5)	N5—H5B	0.90 (1)
C9—H9A	0.930	O3—H3A	0.85 (1)
C10—C11	1.392 (4)	O3—H3B	0.85 (1)
C10—H10A	0.930	O4—H4A	0.85 (1)
C11—C12	1.380 (3)	O4—H4B	0.85 (1)
C5—C1—C12	120.04 (17)	C12—C11—H11A	120.4
C5—C1—C6	110.78 (17)	C10—C11—H11A	120.4
C12—C1—C6	101.37 (17)	C11—C12—C7	119.2 (2)
C5—C1—C2	101.12 (16)	C11—C12—C1	132.7 (2)
C12—C1—C2	113.93 (17)	C7—C12—C1	108.0 (2)
C6—C1—C2	109.64 (16)	O2—C13—N2	127.39 (19)
C19—C2—C13	102.28 (17)	O2—C13—C2	125.34 (19)
C19—C2—C3	118.76 (17)	N2—C13—C2	107.25 (16)
C13—C2—C3	106.69 (16)	C15—C14—C19	122.0 (2)
C19—C2—C1	116.18 (17)	C15—C14—N2	128.3 (2)
C13—C2—C1	107.57 (15)	C19—C14—N2	109.72 (18)
C3—C2—C1	104.56 (15)	C14—C15—C16	117.2 (2)
C21—C3—C20	106.75 (19)	C14—C15—H15A	121.4
C21—C3—C4	110.04 (18)	C16—C15—H15A	121.4
C20—C3—C4	112.24 (19)	C17—C16—C15	121.9 (2)
C21—C3—C2	113.62 (17)	C17—C16—H16A	119.1
C20—C3—C2	111.58 (18)	C15—C16—H16A	119.1
C4—C3—C2	102.72 (16)	C16—C17—C18	120.6 (2)
N5—C4—C5	130.6 (2)	C16—C17—H17A	119.7
N5—C4—C3	119.7 (2)	C18—C17—H17A	119.7
C5—C4—C3	109.72 (18)	C19—C18—C17	118.6 (3)
C4—C5—C22	121.9 (2)	C19—C18—H18A	120.7
C4—C5—C1	114.59 (18)	C17—C18—H18A	120.7
C22—C5—C1	123.10 (19)	C18—C19—C14	119.7 (2)
O1—C6—N1	127.3 (2)	C18—C19—C2	132.2 (2)
O1—C6—C1	124.5 (2)	C14—C19—C2	107.96 (18)
N1—C6—C1	108.2 (2)	N3—C20—C3	179.4 (3)
C8—C7—C12	122.4 (3)	N4—C21—C3	178.0 (3)
C8—C7—N1	127.5 (2)	N6—C22—C5	178.1 (3)
C12—C7—N1	110.0 (2)	C6—N1—C7	111.51 (19)
C7—C8—C9	117.3 (3)	C6—N1—H1	124.2
C7—C8—H8A	121.3	C7—N1—H1	124.2
C9—C8—H8A	121.3	C13—N2—C14	112.51 (18)
C8—C9—C10	121.7 (3)	C13—N2—H2	123.7
C8—C9—H9A	119.1	C14—N2—H2	123.7
C10—C9—H9A	119.1	C4—N5—H5A	119.9 (19)
C9—C10—C11	120.1 (3)	C4—N5—H5B	123 (3)
C9—C10—H10A	119.9	H5A—N5—H5B	115 (3)
C11—C10—H10A	119.9	H3A—O3—H3B	105.1 (17)
C12—C11—C10	119.1 (2)	H4A—O4—H4B	104.8 (17)
C5—C1—C2—C19	158.77 (17)	C9—C10—C11—C12	0.7 (4)
C12—C1—C2—C19	−71.0 (2)	C10—C11—C12—C7	−2.2 (4)
C6—C1—C2—C19	41.8 (2)	C10—C11—C12—C1	179.7 (2)
C5—C1—C2—C13	−87.37 (18)	C8—C7—C12—C11	2.5 (4)
C12—C1—C2—C13	42.8 (2)	N1—C7—C12—C11	−175.0 (2)
C6—C1—C2—C13	155.61 (17)	C8—C7—C12—C1	−179.0 (2)
C5—C1—C2—C3	25.79 (18)	N1—C7—C12—C1	3.5 (3)
C12—C1—C2—C3	155.99 (17)	C5—C1—C12—C11	48.3 (4)
C6—C1—C2—C3	−91.22 (18)	C6—C1—C12—C11	170.6 (2)
C19—C2—C3—C21	−37.6 (3)	C2—C1—C12—C11	−71.8 (3)
C13—C2—C3—C21	−152.32 (18)	C5—C1—C12—C7	−130.0 (2)
C1—C2—C3—C21	93.88 (19)	C6—C1—C12—C7	−7.7 (2)
C19—C2—C3—C20	83.1 (2)	C2—C1—C12—C7	110.0 (2)
C13—C2—C3—C20	−31.6 (2)	C19—C2—C13—O2	−173.2 (2)
C1—C2—C3—C20	−145.38 (18)	C3—C2—C13—O2	−47.8 (3)
C19—C2—C3—C4	−156.44 (18)	C1—C2—C13—O2	63.9 (3)
C13—C2—C3—C4	88.85 (18)	C19—C2—C13—N2	5.2 (2)
C1—C2—C3—C4	−24.95 (19)	C3—C2—C13—N2	130.60 (18)
C21—C3—C4—N5	72.4 (3)	C1—C2—C13—N2	−117.67 (18)
C20—C3—C4—N5	−46.3 (3)	C19—C14—C15—C16	−0.5 (4)
C2—C3—C4—N5	−166.3 (2)	N2—C14—C15—C16	−179.2 (2)
C21—C3—C4—C5	−106.6 (2)	C14—C15—C16—C17	0.1 (4)
C20—C3—C4—C5	134.7 (2)	C15—C16—C17—C18	0.4 (5)
C2—C3—C4—C5	14.7 (2)	C16—C17—C18—C19	−0.4 (5)
N5—C4—C5—C22	−3.5 (4)	C17—C18—C19—C14	0.0 (4)
C3—C4—C5—C22	175.3 (2)	C17—C18—C19—C2	175.9 (3)
N5—C4—C5—C1	−176.4 (2)	C15—C14—C19—C18	0.4 (4)
C3—C4—C5—C1	2.4 (3)	N2—C14—C19—C18	179.4 (2)
C12—C1—C5—C4	−144.5 (2)	C15—C14—C19—C2	−176.4 (2)
C6—C1—C5—C4	97.9 (2)	N2—C14—C19—C2	2.6 (3)
C2—C1—C5—C4	−18.3 (2)	C13—C2—C19—C18	179.1 (3)
C12—C1—C5—C22	42.7 (3)	C3—C2—C19—C18	62.1 (4)
C6—C1—C5—C22	−74.9 (3)	C1—C2—C19—C18	−64.0 (3)
C2—C1—C5—C22	168.9 (2)	C13—C2—C19—C14	−4.6 (2)
C5—C1—C6—O1	−41.8 (3)	C3—C2—C19—C14	−121.6 (2)
C12—C1—C6—O1	−170.3 (2)	C1—C2—C19—C14	112.2 (2)
C2—C1—C6—O1	68.9 (3)	O1—C6—N1—C7	171.7 (2)
C5—C1—C6—N1	138.14 (19)	C1—C6—N1—C7	−8.3 (3)
C12—C1—C6—N1	9.6 (2)	C8—C7—N1—C6	−174.1 (3)
C2—C1—C6—N1	−111.1 (2)	C12—C7—N1—C6	3.2 (3)
C12—C7—C8—C9	−1.1 (4)	O2—C13—N2—C14	174.4 (2)
N1—C7—C8—C9	176.0 (3)	C2—C13—N2—C14	−4.0 (2)
C7—C8—C9—C10	−0.5 (5)	C15—C14—N2—C13	179.9 (2)
C8—C9—C10—C11	0.7 (5)	C19—C14—N2—C13	1.0 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2i	0.86	2.09	2.905 (2)	158
N2—H2···O3i	0.86	2.22	3.032 (3)	157
O3—H3A···O1ii	0.85 (1)	2.00 (2)	2.795 (3)	157 (4)
O3—H3B···N6iii	0.85 (1)	2.22 (5)	2.834 (3)	129 (5)
O3—H3B···O4iv	0.85 (1)	2.62 (3)	3.381 (4)	149 (5)
O4—H4A···N4v	0.85 (1)	2.38 (3)	3.171 (5)	155 (7)
O4—H4B···N3	0.85 (1)	2.68 (4)	3.392 (4)	142 (6)
N5—H5A···O3vi	0.90 (1)	1.97 (1)	2.860 (3)	175 (3)
N5—H5B···O4vi	0.90 (1)	2.17 (1)	3.061 (4)	171 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2i	0.86	2.09	2.905 (2)	158
N2—H2⋯O3i	0.86	2.22	3.032 (3)	157
O3—H3A⋯O1ii	0.85 (1)	2.00 (2)	2.795 (3)	157 (4)
O3—H3B⋯N6iii	0.85 (1)	2.22 (5)	2.834 (3)	129 (5)
O3—H3B⋯O4iv	0.85 (1)	2.62 (3)	3.381 (4)	149 (5)
O4—H4A⋯N4v	0.85 (1)	2.38 (3)	3.171 (5)	155 (7)
O4—H4B⋯N3	0.85 (1)	2.68 (4)	3.392 (4)	142 (6)
N5—H5A⋯O3vi	0.90 (1)	1.97 (1)	2.860 (3)	175 (3)
N5—H5B⋯O4vi	0.90 (1)	2.17 (1)	3.061 (4)	171 (3)

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