N(1),N(4),3,6-Tetra-methyl-1,2,4,5-tetra-zine-1,4-dicarboxamide.

The asymmetric unit of the title compound, C(8)H(14)N(6)O(2), contains two independent mol-ecules. In one mol-ecule, the amide-substituted N atoms of the tetra-zine ring deviate from the plane [maximum deviation = 0.028 (1) Å] through the four other atoms in the ring by 0.350 (2) and 0.344 (2) Å, forming a boat conformation, and the mean planes of the two carboxamide groups form dihedral angles of 10.46 (13) and 20.41 (12)° with the four approximtely planar atoms in the tetra-zine ring. In the other mol-ecule, the amide-substituted N atoms of the tetra-zine ring deviate from the plane [maximum deviation = 0.033 (1) Å] through the four other atoms in the ring by 0.324 (2) and 0.307 (2) Å, forming a boat conformation, and the mean planes of the two carboxamide groups form dihedral angles of 14.66 (11) and 17.08 (10)° with the four approximately planar atoms of the tetra-zine ring. In the crystal, N-H⋯O hydrogen bonds connect mol-ecules to form a two-dimensional network parallel to (1-1-1). Intra-molecular N-H⋯N hydrogen bonds are observed.

Related literature

For chemical reactions of 1,2,4,5-tetra­zine derivatives, see: Domingo et al. (2009 ▶); Lorincz et al. (2010 ▶) and for their biological activity, see: Devaraj et al. (2009 ▶); Eremeev et al. (1978 ▶, 1980 ▶); Han et al. (2010 ▶); Neunhoeffer (1984 ▶); Sauer (1996 ▶). For the anti­tumor activity of 1,2,4,5-tetra­zine derivatives, see: Hu et al. (2002 ▶, 2004 ▶); Rao & Hu (2005 ▶, 2006 ▶). For standard bond lengths, see: Allen et al. (1987 ▶). For the synthesis of the title compound, see: Hu et al. (2004 ▶); Rao et al. (2012 ▶); Sun et al. (2003 ▶).

Experimental

Crystal data

C8H14N6O2

M = 226.25

Triclinic,

a = 9.0002 (17) Å

b = 12.045 (2) Å

c = 12.357 (2) Å

α = 118.386 (2)°

β = 101.701 (3)°

γ = 99.494 (3)°

V = 1099.6 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 298 K

0.34 × 0.30 × 0.15 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1997 ▶) T min = 0.966, T max = 0.985

5571 measured reflections

3809 independent reflections

3178 reflections with I > 2σ(I)

R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.115

S = 1.06

3809 reflections

298 parameters

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.19 e Å−3

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); 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 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812022519/lh5475sup1.cif

Supplementary material file. DOI: 10.1107/S1600536812022519/lh5475Isup2.cdx

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812022519/lh5475Isup3.hkl

Supplementary material file. DOI: 10.1107/S1600536812022519/lh5475Isup4.cml

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

C8H14N6O2	Z = 4
Mr = 226.25	F(000) = 480
Triclinic, P1	Dx = 1.367 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.0002 (17) Å	Cell parameters from 2161 reflections
b = 12.045 (2) Å	θ = 2.4–26.0°
c = 12.357 (2) Å	µ = 0.10 mm−1
α = 118.386 (2)°	T = 298 K
β = 101.701 (3)°	Block, colourless
γ = 99.494 (3)°	0.34 × 0.30 × 0.15 mm
V = 1099.6 (4) Å3

Bruker SMART CCD diffractometer	3809 independent reflections
Radiation source: fine-focus sealed tube	3178 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.018
φ and ω scans	θmax = 25.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −10→10
Tmin = 0.966, Tmax = 0.985	k = −14→11
5571 measured reflections	l = −11→14

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)] = 0.044	H-atom parameters constrained
wR(F2) = 0.115	w = 1/[σ2(Fo2) + (0.0511P)2 + 0.2386P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max < 0.001
3809 reflections	Δρmax = 0.17 e Å−3
298 parameters	Δρmin = −0.19 e Å−3
0 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: 0.028 (2)

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
O2	0.65578 (15)	1.05745 (12)	0.47718 (12)	0.0481 (3)
O4	0.89425 (15)	0.52517 (12)	0.38657 (12)	0.0485 (3)
O3	1.24324 (16)	0.92428 (15)	1.04950 (13)	0.0591 (4)
O1	0.31715 (16)	0.38004 (14)	0.09001 (15)	0.0624 (4)
N11	1.11229 (17)	0.83375 (14)	0.67258 (14)	0.0413 (4)
N5	0.42071 (17)	0.76464 (15)	0.18158 (14)	0.0428 (4)
N8	0.90988 (17)	0.73177 (15)	0.76534 (14)	0.0441 (4)
N1	0.48121 (17)	0.59229 (14)	0.19776 (14)	0.0427 (4)
N4	0.54445 (17)	0.84531 (14)	0.30278 (14)	0.0408 (4)
N2	0.64314 (17)	0.67031 (15)	0.26959 (15)	0.0456 (4)
N10	0.99591 (17)	0.70658 (13)	0.59312 (13)	0.0401 (4)
N7	1.06880 (17)	0.81490 (15)	0.84255 (14)	0.0424 (4)
C5	0.5569 (2)	0.98150 (17)	0.36969 (17)	0.0389 (4)
C9	0.8816 (2)	0.67574 (17)	0.64282 (17)	0.0389 (4)
N12	1.10612 (19)	0.69002 (15)	0.43553 (14)	0.0459 (4)
H12	1.1731	0.7660	0.4950	0.055*
C12	1.1485 (2)	0.88147 (16)	0.79504 (16)	0.0378 (4)
N3	0.57057 (19)	0.42708 (15)	0.20694 (15)	0.0479 (4)
H3	0.6588	0.4886	0.2591	0.058*
C4	0.4495 (2)	0.45756 (18)	0.15889 (17)	0.0432 (4)
N6	0.45245 (19)	1.01525 (15)	0.30820 (15)	0.0470 (4)
H6	0.3919	0.9577	0.2297	0.056*
N9	0.99787 (19)	0.79818 (17)	1.00444 (15)	0.0511 (4)
H9	0.9073	0.7470	0.9458	0.061*
C14	0.9928 (2)	0.63353 (17)	0.46360 (16)	0.0379 (4)
C3	0.6682 (2)	0.79506 (18)	0.32349 (17)	0.0408 (4)
C13	1.1104 (2)	0.85187 (18)	0.97372 (17)	0.0425 (4)
C6	0.3891 (2)	0.64048 (18)	0.13459 (17)	0.0394 (4)
C10	0.7187 (2)	0.5826 (2)	0.55809 (19)	0.0531 (5)
H10A	0.6737	0.6075	0.4987	0.080*
H10B	0.6527	0.5861	0.6110	0.080*
H10C	0.7249	0.4941	0.5100	0.080*
C11	1.2743 (2)	1.01175 (18)	0.88275 (18)	0.0505 (5)
H11A	1.2369	1.0699	0.9493	0.076*
H11B	1.2985	1.0501	0.8334	0.076*
H11C	1.3685	0.9993	0.9221	0.076*
C1	0.8344 (2)	0.88257 (19)	0.4028 (2)	0.0555 (5)
H1A	0.8627	0.9432	0.3753	0.083*
H1B	0.9055	0.8296	0.3914	0.083*
H1C	0.8422	0.9314	0.4929	0.083*
C2	0.2535 (2)	0.5519 (2)	0.01109 (18)	0.0531 (5)
H2A	0.2876	0.4846	−0.0507	0.080*
H2B	0.2182	0.6029	−0.0235	0.080*
H2C	0.1676	0.5110	0.0279	0.080*
C15	1.0255 (3)	0.8246 (2)	1.13515 (19)	0.0585 (6)
H15A	0.9317	0.7778	1.1395	0.088*
H15B	1.0496	0.9179	1.1949	0.088*
H15C	1.1133	0.7955	1.1578	0.088*
C7	0.5575 (3)	0.29262 (19)	0.1735 (2)	0.0622 (6)
H7A	0.6410	0.2931	0.2361	0.093*
H7B	0.5669	0.2428	0.0886	0.093*
H7C	0.4561	0.2527	0.1736	0.093*
C8	0.4394 (3)	1.1471 (2)	0.3715 (2)	0.0615 (6)
H8A	0.3507	1.1515	0.3172	0.092*
H8B	0.5354	1.2086	0.3867	0.092*
H8C	0.4235	1.1694	0.4530	0.092*
C16	1.1183 (3)	0.6249 (2)	0.30563 (19)	0.0606 (6)
H16A	1.2061	0.6797	0.3028	0.091*
H16B	1.0215	0.6108	0.2444	0.091*
H16C	1.1354	0.5413	0.2838	0.091*

	U11	U22	U33	U12	U13	U23
O2	0.0450 (7)	0.0421 (7)	0.0381 (7)	0.0013 (6)	0.0023 (6)	0.0150 (6)
O4	0.0481 (8)	0.0373 (7)	0.0384 (7)	0.0026 (6)	0.0046 (6)	0.0109 (6)
O3	0.0435 (8)	0.0760 (10)	0.0429 (8)	−0.0041 (7)	−0.0020 (6)	0.0335 (8)
O1	0.0390 (8)	0.0510 (8)	0.0730 (10)	−0.0083 (7)	−0.0028 (7)	0.0297 (8)
N11	0.0412 (9)	0.0335 (8)	0.0358 (8)	0.0004 (6)	0.0062 (7)	0.0142 (7)
N5	0.0354 (8)	0.0437 (9)	0.0340 (8)	0.0057 (7)	0.0019 (7)	0.0148 (7)
N8	0.0333 (8)	0.0458 (9)	0.0382 (9)	0.0007 (7)	0.0040 (7)	0.0176 (7)
N1	0.0308 (8)	0.0387 (8)	0.0433 (9)	0.0011 (6)	0.0026 (7)	0.0170 (7)
N4	0.0337 (8)	0.0375 (8)	0.0354 (8)	0.0039 (6)	0.0007 (6)	0.0139 (7)
N2	0.0311 (8)	0.0403 (9)	0.0478 (9)	0.0012 (7)	−0.0003 (7)	0.0183 (7)
N10	0.0405 (8)	0.0330 (8)	0.0312 (8)	−0.0004 (6)	0.0054 (6)	0.0114 (6)
N7	0.0351 (8)	0.0463 (9)	0.0337 (8)	0.0013 (7)	0.0041 (6)	0.0184 (7)
C5	0.0347 (9)	0.0410 (10)	0.0344 (10)	0.0026 (8)	0.0086 (8)	0.0189 (8)
C9	0.0371 (10)	0.0357 (9)	0.0355 (10)	0.0080 (8)	0.0059 (8)	0.0157 (8)
N12	0.0478 (9)	0.0414 (8)	0.0337 (8)	0.0040 (7)	0.0104 (7)	0.0130 (7)
C12	0.0356 (9)	0.0359 (9)	0.0345 (10)	0.0071 (7)	0.0074 (8)	0.0157 (8)
N3	0.0419 (9)	0.0375 (8)	0.0465 (9)	0.0002 (7)	−0.0005 (7)	0.0184 (7)
C4	0.0376 (10)	0.0399 (10)	0.0386 (10)	−0.0003 (8)	0.0084 (8)	0.0162 (8)
N6	0.0510 (10)	0.0433 (9)	0.0371 (8)	0.0113 (7)	0.0055 (7)	0.0184 (7)
N9	0.0410 (9)	0.0636 (11)	0.0379 (9)	0.0014 (8)	0.0068 (7)	0.0257 (8)
C14	0.0378 (10)	0.0345 (9)	0.0340 (9)	0.0101 (8)	0.0042 (8)	0.0158 (8)
C3	0.0355 (10)	0.0417 (10)	0.0388 (10)	0.0050 (8)	0.0065 (8)	0.0206 (8)
C13	0.0381 (10)	0.0469 (11)	0.0361 (10)	0.0085 (8)	0.0051 (8)	0.0211 (9)
C6	0.0315 (9)	0.0438 (10)	0.0340 (9)	0.0060 (8)	0.0092 (7)	0.0162 (8)
C10	0.0392 (11)	0.0532 (12)	0.0458 (11)	0.0014 (9)	0.0072 (9)	0.0170 (10)
C11	0.0526 (12)	0.0416 (10)	0.0386 (10)	−0.0013 (9)	0.0072 (9)	0.0152 (9)
C1	0.0326 (10)	0.0471 (11)	0.0675 (14)	0.0022 (9)	−0.0023 (9)	0.0262 (10)
C2	0.0467 (12)	0.0517 (12)	0.0385 (11)	0.0049 (9)	0.0006 (9)	0.0155 (9)
C15	0.0535 (13)	0.0769 (15)	0.0432 (11)	0.0097 (11)	0.0124 (10)	0.0345 (11)
C7	0.0627 (14)	0.0434 (11)	0.0638 (14)	0.0043 (10)	0.0048 (11)	0.0257 (11)
C8	0.0726 (15)	0.0491 (12)	0.0582 (13)	0.0209 (11)	0.0138 (12)	0.0271 (11)
C16	0.0711 (15)	0.0603 (13)	0.0410 (11)	0.0120 (11)	0.0205 (11)	0.0215 (10)

O2—C5	1.221 (2)	N6—H6	0.8600
O4—C14	1.221 (2)	N9—C13	1.327 (2)
O3—C13	1.221 (2)	N9—C15	1.447 (2)
O1—C4	1.217 (2)	N9—H9	0.8600
N11—C12	1.280 (2)	C3—C1	1.487 (2)
N11—N10	1.4251 (19)	C6—C2	1.491 (2)
N5—C6	1.274 (2)	C10—H10A	0.9600
N5—N4	1.418 (2)	C10—H10B	0.9600
N8—C9	1.276 (2)	C10—H10C	0.9600
N8—N7	1.423 (2)	C11—H11A	0.9600
N1—C6	1.400 (2)	C11—H11B	0.9600
N1—C4	1.413 (2)	C11—H11C	0.9600
N1—N2	1.423 (2)	C1—H1A	0.9600
N4—C3	1.388 (2)	C1—H1B	0.9600
N4—C5	1.414 (2)	C1—H1C	0.9600
N2—C3	1.276 (2)	C2—H2A	0.9600
N10—C9	1.386 (2)	C2—H2B	0.9600
N10—C14	1.404 (2)	C2—H2C	0.9600
N7—C12	1.390 (2)	C15—H15A	0.9600
N7—C13	1.406 (2)	C15—H15B	0.9600
C5—N6	1.325 (2)	C15—H15C	0.9600
C9—C10	1.491 (2)	C7—H7A	0.9600
N12—C14	1.328 (2)	C7—H7B	0.9600
N12—C16	1.451 (2)	C7—H7C	0.9600
N12—H12	0.8600	C8—H8A	0.9600
C12—C11	1.489 (2)	C8—H8B	0.9600
N3—C4	1.323 (2)	C8—H8C	0.9600
N3—C7	1.445 (2)	C16—H16A	0.9600
N3—H3	0.8600	C16—H16B	0.9600
N6—C8	1.437 (3)	C16—H16C	0.9600
C12—N11—N10	114.96 (14)	N5—C6—C2	117.15 (17)
C6—N5—N4	115.19 (15)	N1—C6—C2	122.75 (16)
C9—N8—N7	115.02 (15)	C9—C10—H10A	109.5
C6—N1—C4	124.52 (15)	C9—C10—H10B	109.5
C6—N1—N2	116.29 (14)	H10A—C10—H10B	109.5
C4—N1—N2	114.69 (14)	C9—C10—H10C	109.5
C3—N4—C5	124.12 (14)	H10A—C10—H10C	109.5
C3—N4—N5	116.73 (14)	H10B—C10—H10C	109.5
C5—N4—N5	115.63 (14)	C12—C11—H11A	109.5
C3—N2—N1	114.98 (15)	C12—C11—H11B	109.5
C9—N10—C14	125.66 (14)	H11A—C11—H11B	109.5
C9—N10—N11	117.72 (13)	C12—C11—H11C	109.5
C14—N10—N11	115.71 (14)	H11A—C11—H11C	109.5
C12—N7—C13	124.70 (15)	H11B—C11—H11C	109.5
C12—N7—N8	117.36 (14)	C3—C1—H1A	109.5
C13—N7—N8	114.98 (14)	C3—C1—H1B	109.5
O2—C5—N6	124.99 (17)	H1A—C1—H1B	109.5
O2—C5—N4	120.13 (16)	C3—C1—H1C	109.5
N6—C5—N4	114.86 (15)	H1A—C1—H1C	109.5
N8—C9—N10	120.67 (16)	H1B—C1—H1C	109.5
N8—C9—C10	116.79 (17)	C6—C2—H2A	109.5
N10—C9—C10	122.46 (16)	C6—C2—H2B	109.5
C14—N12—C16	120.73 (16)	H2A—C2—H2B	109.5
C14—N12—H12	119.6	C6—C2—H2C	109.5
C16—N12—H12	119.6	H2A—C2—H2C	109.5
N11—C12—N7	120.50 (15)	H2B—C2—H2C	109.5
N11—C12—C11	117.34 (16)	N9—C15—H15A	109.5
N7—C12—C11	122.13 (15)	N9—C15—H15B	109.5
C4—N3—C7	121.39 (16)	H15A—C15—H15B	109.5
C4—N3—H3	119.3	N9—C15—H15C	109.5
C7—N3—H3	119.3	H15A—C15—H15C	109.5
O1—C4—N3	124.76 (18)	H15B—C15—H15C	109.5
O1—C4—N1	120.22 (17)	N3—C7—H7A	109.5
N3—C4—N1	114.97 (15)	N3—C7—H7B	109.5
C5—N6—C8	120.58 (16)	H7A—C7—H7B	109.5
C5—N6—H6	119.7	N3—C7—H7C	109.5
C8—N6—H6	119.7	H7A—C7—H7C	109.5
C13—N9—C15	120.93 (16)	H7B—C7—H7C	109.5
C13—N9—H9	119.5	N6—C8—H8A	109.5
C15—N9—H9	119.5	N6—C8—H8B	109.5
O4—C14—N12	124.41 (16)	H8A—C8—H8B	109.5
O4—C14—N10	120.80 (16)	N6—C8—H8C	109.5
N12—C14—N10	114.76 (15)	H8A—C8—H8C	109.5
N2—C3—N4	120.34 (16)	H8B—C8—H8C	109.5
N2—C3—C1	117.75 (17)	N12—C16—H16A	109.5
N4—C3—C1	121.85 (16)	N12—C16—H16B	109.5
O3—C13—N9	124.37 (17)	H16A—C16—H16B	109.5
O3—C13—N7	120.74 (17)	N12—C16—H16C	109.5
N9—C13—N7	114.83 (16)	H16A—C16—H16C	109.5
N5—C6—N1	120.09 (15)	H16B—C16—H16C	109.5
C6—N5—N4—C3	33.9 (2)	C6—N1—C4—N3	162.35 (16)
C6—N5—N4—C5	−166.36 (15)	N2—N1—C4—N3	7.1 (2)
C6—N1—N2—C3	33.9 (2)	O2—C5—N6—C8	−5.5 (3)
C4—N1—N2—C3	−168.75 (16)	N4—C5—N6—C8	172.64 (16)
C12—N11—N10—C9	31.0 (2)	C16—N12—C14—O4	1.3 (3)
C12—N11—N10—C14	−159.33 (16)	C16—N12—C14—N10	179.32 (17)
C9—N8—N7—C12	32.6 (2)	C9—N10—C14—O4	−8.9 (3)
C9—N8—N7—C13	−165.91 (16)	N11—N10—C14—O4	−177.71 (15)
C3—N4—C5—O2	−25.0 (3)	C9—N10—C14—N12	172.96 (16)
N5—N4—C5—O2	176.99 (15)	N11—N10—C14—N12	4.2 (2)
C3—N4—C5—N6	156.80 (16)	N1—N2—C3—N4	−4.4 (2)
N5—N4—C5—N6	−1.2 (2)	N1—N2—C3—C1	178.52 (17)
N7—N8—C9—N10	−6.1 (2)	C5—N4—C3—N2	172.45 (16)
N7—N8—C9—C10	177.08 (15)	N5—N4—C3—N2	−29.7 (2)
C14—N10—C9—N8	165.74 (17)	C5—N4—C3—C1	−10.6 (3)
N11—N10—C9—N8	−25.7 (2)	N5—N4—C3—C1	147.23 (18)
C14—N10—C9—C10	−17.6 (3)	C15—N9—C13—O3	1.0 (3)
N11—N10—C9—C10	150.96 (17)	C15—N9—C13—N7	178.38 (17)
N10—N11—C12—N7	−4.4 (2)	C12—N7—C13—O3	−19.3 (3)
N10—N11—C12—C11	177.61 (16)	N8—N7—C13—O3	−179.19 (17)
C13—N7—C12—N11	173.17 (17)	C12—N7—C13—N9	163.24 (17)
N8—N7—C12—N11	−27.3 (2)	N8—N7—C13—N9	3.3 (2)
C13—N7—C12—C11	−8.9 (3)	N4—N5—C6—N1	−4.2 (2)
N8—N7—C12—C11	150.58 (17)	N4—N5—C6—C2	176.52 (15)
C7—N3—C4—O1	4.1 (3)	C4—N1—C6—N5	175.41 (16)
C7—N3—C4—N1	−178.51 (17)	N2—N1—C6—N5	−29.7 (2)
C6—N1—C4—O1	−20.2 (3)	C4—N1—C6—C2	−5.3 (3)
N2—N1—C4—O1	−175.36 (16)	N2—N1—C6—C2	149.51 (17)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···N2	0.86	2.16	2.572 (2)	108
N6—H6···N5	0.86	2.19	2.586 (2)	108
N9—H9···N8	0.86	2.15	2.567 (2)	109
N12—H12···N11	0.86	2.17	2.581 (2)	109
N3—H3···O4	0.86	2.20	2.925 (2)	142
N6—H6···O3i	0.86	2.16	2.918 (2)	146
N9—H9···O1ii	0.86	2.14	2.877 (3)	143
N12—H12···O2iii	0.86	2.24	2.967 (3)	142

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3⋯N2	0.86	2.16	2.572 (2)	108
N6—H6⋯N5	0.86	2.19	2.586 (2)	108
N9—H9⋯N8	0.86	2.15	2.567 (2)	109
N12—H12⋯N11	0.86	2.17	2.581 (2)	109
N3—H3⋯O4	0.86	2.20	2.925 (2)	142
N6—H6⋯O3i	0.86	2.16	2.918 (2)	146
N9—H9⋯O1ii	0.86	2.14	2.877 (3)	143
N12—H12⋯O2iii	0.86	2.24	2.967 (3)	142

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