Racemic N-methyl-4-[2-(methyl-sulfan-yl)-pyrimidin-4-yl]-1-(tetra-hydro-furan-3-yl)-1H-pyrazol-5-amine.

The title compound, C(13)H(17)N(5)OS, was obtained by cyclo-addition of 2-[2-(methyl-sulfan-yl)pyrimidin-4-yl]-3-oxo-propane-nitrile with (tetra-hydro-furan-3-yl)hydrazine dihydro-chloride and subsequent N-methyl-ation of 4-[2-(methyl-sulfan-yl)-pyrimidin-4-yl]-1-(tetra-hydro-furan-2-yl)-1H-pyrazol-5-amine with methyl iodide. The two mol-ecules in the asymmetric unit have opposite absolute configurations and are related by a noncrystallographic inversion center. Both feature intra-mol-ecular N-H⋯N hydrogen bonds. The geometry of the mol-ecules is similar to that observed in the structure of a single enanti-omer of the title compound.

Related literature

For the structure of the R-enanti­omer component of the racemic title compound, see: Liu et al. (2009a ▶). For details of the synthesis of the title compound, see: Liu et al. (2009a ▶,b ▶).

Experimental

Crystal data

C13H17N5OS

M = 291.38

Monoclinic,

a = 15.7404 (5) Å

b = 10.1515 (3) Å

c = 18.9644 (6) Å

β = 112.829 (1)°

V = 2792.92 (15) Å3

Z = 8

Cu Kα radiation

μ = 2.10 mm−1

T = 100 K

0.30 × 0.20 × 0.20 mm

Data collection

Bruker P4/APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.572, T max = 0.679

18618 measured reflections

5007 independent reflections

4521 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.119

S = 1.05

5007 reflections

371 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.88 e Å−3

Δρmin = −0.32 e Å−3

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-32 (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809014317/dn2448sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809014317/dn2448Isup2.hkl

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

C13H17N5OS	F(000) = 1232
Mr = 291.38	Dx = 1.386 Mg m−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2yn	Cell parameters from 1033 reflections
a = 15.7404 (5) Å	θ = 4.9–54.9°
b = 10.1515 (3) Å	µ = 2.10 mm−1
c = 18.9644 (6) Å	T = 100 K
β = 112.829 (1)°	Block, colorless
V = 2792.92 (15) Å3	0.30 × 0.20 × 0.20 mm
Z = 8

Bruker P4/APEX CCD diffractometer	5007 independent reflections
Radiation source: fine-focus sealed tube	4521 reflections with I > 2σ(I)
graphite	Rint = 0.030
ω scans	θmax = 68.6°, θmin = 3.1°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −18→18
Tmin = 0.572, Tmax = 0.679	k = −11→12
18618 measured reflections	l = −22→21

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.119	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0596P)2 + 1.859P] where P = (Fo2 + 2Fc2)/3
5007 reflections	(Δ/σ)max = 0.001
371 parameters	Δρmax = 0.88 e Å−3
0 restraints	Δρmin = −0.32 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
C1	0.22461 (16)	−0.1765 (2)	0.31756 (13)	0.0393 (5)
H1A	0.1969	−0.2521	0.2834	0.047*
H1B	0.2861	−0.1583	0.3170	0.047*
C2	0.16265 (14)	−0.0551 (2)	0.29178 (11)	0.0310 (4)
H2A	0.0969	−0.0805	0.2670	0.037*
H2B	0.1794	−0.0008	0.2558	0.037*
C3	0.18197 (12)	0.01907 (18)	0.36747 (10)	0.0213 (4)
H3	0.2191	0.0998	0.3691	0.026*
C4	0.24143 (13)	−0.07910 (18)	0.42835 (11)	0.0249 (4)
H4A	0.3068	−0.0511	0.4489	0.030*
H4B	0.2204	−0.0836	0.4712	0.030*
C5	−0.01506 (12)	0.02935 (18)	0.41206 (10)	0.0208 (4)
H5	−0.0595	−0.0101	0.4279	0.025*
C6	−0.01006 (12)	0.16645 (17)	0.40075 (10)	0.0199 (4)
C7	0.06411 (12)	0.17913 (17)	0.37729 (10)	0.0196 (4)
C8	0.11656 (13)	0.29925 (19)	0.28860 (11)	0.0263 (4)
H8A	0.1802	0.2726	0.2992	0.039*
H8B	0.1069	0.3899	0.2693	0.039*
H8C	0.0740	0.2402	0.2501	0.039*
C9	−0.06565 (12)	0.27261 (18)	0.41090 (10)	0.0203 (4)
C10	−0.13890 (13)	0.25167 (19)	0.43403 (11)	0.0256 (4)
H10	−0.1566	0.1654	0.4423	0.031*
C11	−0.18401 (13)	0.3611 (2)	0.44425 (11)	0.0289 (4)
H11	−0.2330	0.3485	0.4611	0.035*
C12	−0.09392 (12)	0.49396 (18)	0.40780 (10)	0.0231 (4)
C13	0.02328 (15)	0.6340 (2)	0.35791 (13)	0.0331 (5)
H13A	0.0731	0.5852	0.3971	0.050*
H13B	0.0462	0.7201	0.3499	0.050*
H13C	0.0015	0.5842	0.3099	0.050*
C14	−0.23088 (16)	0.4429 (2)	0.17690 (13)	0.0387 (5)
H14A	−0.2920	0.4220	0.1775	0.046*
H14B	−0.2054	0.5207	0.2098	0.046*
C15	−0.16593 (14)	0.3254 (2)	0.20499 (11)	0.0324 (5)
H15A	−0.1816	0.2714	0.2417	0.039*
H15B	−0.1009	0.3544	0.2295	0.039*
C16	−0.18296 (12)	0.24857 (18)	0.13061 (10)	0.0220 (4)
H16	−0.2189	0.1669	0.1297	0.026*
C17	−0.24264 (13)	0.34274 (19)	0.06774 (11)	0.0271 (4)
H17A	−0.2190	0.3484	0.0265	0.033*
H17B	−0.3071	0.3110	0.0454	0.033*
C18	0.01589 (12)	0.24134 (17)	0.08857 (10)	0.0204 (4)
H18	0.0601	0.2813	0.0726	0.025*
C19	0.01176 (12)	0.10435 (17)	0.10037 (10)	0.0191 (4)
C20	−0.06290 (12)	0.09089 (17)	0.12278 (9)	0.0188 (3)
C21	−0.11957 (13)	−0.03136 (19)	0.20869 (11)	0.0262 (4)
H21A	−0.0808	0.0312	0.2471	0.039*
H21B	−0.1069	−0.1210	0.2293	0.039*
H21C	−0.1847	−0.0103	0.1958	0.039*
C22	0.06828 (11)	−0.00076 (18)	0.09110 (9)	0.0193 (4)
C23	0.14461 (12)	0.02003 (18)	0.07200 (10)	0.0224 (4)
H23	0.1631	0.1063	0.0646	0.027*
C24	0.19188 (12)	−0.08969 (19)	0.06428 (11)	0.0247 (4)
H24	0.2430	−0.0772	0.0502	0.030*
C25	0.09580 (12)	−0.22284 (18)	0.09390 (10)	0.0216 (4)
C26	−0.03578 (16)	−0.3636 (2)	0.12571 (14)	0.0366 (5)
H26A	−0.0215	−0.3133	0.1730	0.055*
H26B	−0.0608	−0.4498	0.1308	0.055*
H26C	−0.0814	−0.3155	0.0829	0.055*
N1	0.09784 (10)	0.05689 (15)	0.37756 (8)	0.0199 (3)
N2	0.04867 (10)	−0.03777 (15)	0.39826 (8)	0.0217 (3)
N3	0.09942 (11)	0.29183 (15)	0.35925 (9)	0.0220 (3)
N4	−0.16316 (11)	0.48479 (16)	0.43195 (10)	0.0283 (4)
N5	−0.04410 (10)	0.39615 (15)	0.39708 (8)	0.0212 (3)
N6	−0.09717 (10)	0.21269 (14)	0.12244 (8)	0.0197 (3)
N7	−0.04837 (10)	0.30785 (14)	0.10218 (8)	0.0215 (3)
N8	−0.09920 (11)	−0.02230 (15)	0.13985 (9)	0.0215 (3)
N9	0.16958 (10)	−0.21327 (16)	0.07561 (9)	0.0249 (3)
N10	0.04399 (10)	−0.12520 (15)	0.10180 (8)	0.0200 (3)
O1	0.23183 (11)	−0.20351 (14)	0.39248 (9)	0.0365 (4)
O2	−0.23835 (12)	0.46761 (15)	0.10208 (9)	0.0398 (4)
S1	−0.07026 (3)	0.65654 (5)	0.38885 (3)	0.02884 (14)
S2	0.06756 (3)	−0.38593 (4)	0.10801 (3)	0.02817 (14)
H3N	0.0715 (16)	0.355 (2)	0.3657 (13)	0.034*
H8N	−0.0682 (16)	−0.085 (2)	0.1349 (13)	0.034*

	U11	U22	U33	U12	U13	U23
C1	0.0401 (12)	0.0408 (13)	0.0374 (12)	0.0094 (10)	0.0153 (9)	−0.0107 (10)
C2	0.0277 (10)	0.0418 (12)	0.0246 (10)	0.0030 (9)	0.0113 (8)	−0.0049 (8)
C3	0.0195 (8)	0.0206 (9)	0.0254 (9)	0.0011 (7)	0.0106 (7)	0.0006 (7)
C4	0.0231 (9)	0.0236 (9)	0.0296 (10)	0.0047 (7)	0.0120 (8)	0.0033 (7)
C5	0.0199 (8)	0.0209 (9)	0.0222 (9)	−0.0021 (7)	0.0087 (7)	0.0011 (7)
C6	0.0193 (8)	0.0195 (9)	0.0207 (8)	−0.0008 (7)	0.0075 (7)	0.0006 (7)
C7	0.0184 (8)	0.0184 (8)	0.0209 (8)	−0.0011 (7)	0.0063 (7)	−0.0005 (7)
C8	0.0240 (9)	0.0270 (10)	0.0272 (9)	0.0014 (8)	0.0091 (7)	0.0066 (8)
C9	0.0183 (8)	0.0200 (9)	0.0205 (8)	0.0001 (7)	0.0054 (7)	0.0005 (7)
C10	0.0228 (9)	0.0240 (10)	0.0313 (10)	−0.0004 (7)	0.0120 (8)	0.0028 (7)
C11	0.0230 (9)	0.0306 (10)	0.0366 (11)	0.0020 (8)	0.0153 (8)	0.0025 (8)
C12	0.0199 (8)	0.0225 (9)	0.0239 (9)	0.0006 (7)	0.0051 (7)	−0.0018 (7)
C13	0.0408 (11)	0.0218 (10)	0.0438 (12)	−0.0044 (8)	0.0242 (10)	−0.0009 (8)
C14	0.0423 (12)	0.0363 (12)	0.0386 (12)	0.0071 (10)	0.0168 (10)	−0.0073 (9)
C15	0.0290 (10)	0.0423 (12)	0.0265 (10)	0.0078 (9)	0.0114 (8)	−0.0052 (9)
C16	0.0209 (8)	0.0214 (9)	0.0257 (9)	0.0022 (7)	0.0113 (7)	0.0010 (7)
C17	0.0253 (9)	0.0277 (10)	0.0298 (10)	0.0070 (8)	0.0123 (8)	0.0044 (8)
C18	0.0207 (8)	0.0178 (9)	0.0235 (9)	−0.0015 (7)	0.0092 (7)	−0.0009 (7)
C19	0.0191 (8)	0.0180 (9)	0.0195 (8)	−0.0013 (7)	0.0066 (7)	−0.0007 (6)
C20	0.0195 (8)	0.0166 (8)	0.0188 (8)	−0.0008 (7)	0.0057 (6)	−0.0006 (6)
C21	0.0281 (9)	0.0249 (10)	0.0263 (9)	0.0018 (8)	0.0112 (8)	0.0062 (7)
C22	0.0177 (8)	0.0204 (9)	0.0172 (8)	−0.0002 (7)	0.0040 (6)	−0.0005 (6)
C23	0.0201 (8)	0.0209 (9)	0.0252 (9)	−0.0019 (7)	0.0078 (7)	0.0000 (7)
C24	0.0174 (8)	0.0267 (10)	0.0295 (10)	0.0019 (7)	0.0084 (7)	−0.0005 (7)
C25	0.0213 (8)	0.0195 (9)	0.0217 (9)	0.0019 (7)	0.0057 (7)	−0.0009 (7)
C26	0.0449 (12)	0.0194 (10)	0.0575 (14)	−0.0029 (9)	0.0329 (11)	0.0000 (9)
N1	0.0189 (7)	0.0181 (7)	0.0243 (7)	−0.0004 (6)	0.0102 (6)	0.0012 (6)
N2	0.0231 (7)	0.0177 (7)	0.0251 (8)	−0.0026 (6)	0.0101 (6)	0.0021 (6)
N3	0.0229 (8)	0.0170 (7)	0.0292 (8)	−0.0001 (6)	0.0134 (6)	0.0018 (6)
N4	0.0225 (8)	0.0264 (9)	0.0378 (9)	0.0030 (6)	0.0136 (7)	−0.0009 (7)
N5	0.0189 (7)	0.0209 (8)	0.0217 (7)	−0.0006 (6)	0.0058 (6)	−0.0010 (6)
N6	0.0205 (7)	0.0166 (7)	0.0235 (7)	0.0006 (6)	0.0101 (6)	0.0010 (6)
N7	0.0225 (7)	0.0172 (7)	0.0251 (8)	−0.0016 (6)	0.0098 (6)	0.0006 (6)
N8	0.0235 (8)	0.0160 (7)	0.0282 (8)	0.0016 (6)	0.0136 (6)	0.0020 (6)
N9	0.0192 (7)	0.0231 (8)	0.0311 (8)	0.0031 (6)	0.0085 (6)	−0.0017 (6)
N10	0.0201 (7)	0.0180 (7)	0.0204 (7)	−0.0002 (6)	0.0063 (6)	−0.0011 (6)
O1	0.0445 (9)	0.0246 (7)	0.0426 (8)	0.0084 (6)	0.0194 (7)	−0.0002 (6)
O2	0.0538 (10)	0.0272 (8)	0.0448 (9)	0.0133 (7)	0.0260 (8)	0.0044 (6)
S1	0.0310 (3)	0.0180 (2)	0.0391 (3)	0.00095 (18)	0.0152 (2)	−0.00141 (18)
S2	0.0329 (3)	0.0160 (2)	0.0385 (3)	0.00297 (18)	0.0170 (2)	0.00048 (18)

C1—O1	1.408 (3)	C14—H14A	0.9900
C1—C2	1.529 (3)	C14—H14B	0.9900
C1—H1A	0.9900	C15—C16	1.541 (3)
C1—H1B	0.9900	C15—H15A	0.9900
C2—C3	1.543 (2)	C15—H15B	0.9900
C2—H2A	0.9900	C16—N6	1.464 (2)
C2—H2B	0.9900	C16—C17	1.533 (2)
C3—N1	1.461 (2)	C16—H16	1.0000
C3—C4	1.537 (2)	C17—O2	1.415 (2)
C3—H3	1.0000	C17—H17A	0.9900
C4—O1	1.415 (2)	C17—H17B	0.9900
C4—H4A	0.9900	C18—N7	1.322 (2)
C4—H4B	0.9900	C18—C19	1.414 (2)
C5—N2	1.320 (2)	C18—H18	0.9500
C5—C6	1.415 (2)	C19—C20	1.403 (2)
C5—H5	0.9500	C19—C22	1.443 (2)
C6—C7	1.407 (2)	C20—N6	1.348 (2)
C6—C9	1.447 (2)	C20—N8	1.377 (2)
C7—N1	1.349 (2)	C21—N8	1.463 (2)
C7—N3	1.372 (2)	C21—H21A	0.9800
C8—N3	1.468 (2)	C21—H21B	0.9800
C8—H8A	0.9800	C21—H21C	0.9800
C8—H8B	0.9800	C22—N10	1.358 (2)
C8—H8C	0.9800	C22—C23	1.399 (2)
C9—N5	1.351 (2)	C23—C24	1.378 (3)
C9—C10	1.400 (2)	C23—H23	0.9500
C10—C11	1.372 (3)	C24—N9	1.342 (2)
C10—H10	0.9500	C24—H24	0.9500
C11—N4	1.341 (3)	C25—N10	1.328 (2)
C11—H11	0.9500	C25—N9	1.338 (2)
C12—N5	1.329 (2)	C25—S2	1.7614 (19)
C12—N4	1.339 (2)	C26—S2	1.798 (2)
C12—S1	1.7594 (19)	C26—H26A	0.9800
C13—S1	1.799 (2)	C26—H26B	0.9800
C13—H13A	0.9800	C26—H26C	0.9800
C13—H13B	0.9800	N1—N2	1.383 (2)
C13—H13C	0.9800	N3—H3N	0.82 (2)
C14—O2	1.400 (3)	N6—N7	1.378 (2)
C14—C15	1.526 (3)	N8—H8N	0.83 (2)
O1—C1—C2	105.75 (16)	H15A—C15—H15B	109.1
O1—C1—H1A	110.6	N6—C16—C17	112.64 (14)
C2—C1—H1A	110.6	N6—C16—C15	112.50 (15)
O1—C1—H1B	110.6	C17—C16—C15	103.46 (15)
C2—C1—H1B	110.6	N6—C16—H16	109.4
H1A—C1—H1B	108.7	C17—C16—H16	109.4
C1—C2—C3	102.99 (15)	C15—C16—H16	109.4
C1—C2—H2A	111.2	O2—C17—C16	107.18 (15)
C3—C2—H2A	111.2	O2—C17—H17A	110.3
C1—C2—H2B	111.2	C16—C17—H17A	110.3
C3—C2—H2B	111.2	O2—C17—H17B	110.3
H2A—C2—H2B	109.1	C16—C17—H17B	110.3
N1—C3—C4	112.99 (14)	H17A—C17—H17B	108.5
N1—C3—C2	112.86 (14)	N7—C18—C19	112.69 (16)
C4—C3—C2	103.01 (15)	N7—C18—H18	123.7
N1—C3—H3	109.3	C19—C18—H18	123.7
C4—C3—H3	109.3	C20—C19—C18	103.83 (15)
C2—C3—H3	109.3	C20—C19—C22	126.39 (16)
O1—C4—C3	107.29 (15)	C18—C19—C22	129.77 (16)
O1—C4—H4A	110.3	N6—C20—N8	124.39 (16)
C3—C4—H4A	110.3	N6—C20—C19	106.85 (15)
O1—C4—H4B	110.3	N8—C20—C19	128.72 (16)
C3—C4—H4B	110.3	N8—C21—H21A	109.5
H4A—C4—H4B	108.5	N8—C21—H21B	109.5
N2—C5—C6	112.72 (15)	H21A—C21—H21B	109.5
N2—C5—H5	123.6	N8—C21—H21C	109.5
C6—C5—H5	123.6	H21A—C21—H21C	109.5
C7—C6—C5	103.87 (15)	H21B—C21—H21C	109.5
C7—C6—C9	126.33 (16)	N10—C22—C23	119.94 (16)
C5—C6—C9	129.80 (16)	N10—C22—C19	116.56 (15)
N1—C7—N3	124.83 (16)	C23—C22—C19	123.50 (16)
N1—C7—C6	106.75 (15)	C24—C23—C22	117.31 (17)
N3—C7—C6	128.40 (16)	C24—C23—H23	121.3
N3—C8—H8A	109.5	C22—C23—H23	121.3
N3—C8—H8B	109.5	N9—C24—C23	123.55 (17)
H8A—C8—H8B	109.5	N9—C24—H24	118.2
N3—C8—H8C	109.5	C23—C24—H24	118.2
H8A—C8—H8C	109.5	N10—C25—N9	127.40 (17)
H8B—C8—H8C	109.5	N10—C25—S2	118.83 (14)
N5—C9—C10	120.07 (16)	N9—C25—S2	113.77 (13)
N5—C9—C6	117.08 (15)	S2—C26—H26A	109.5
C10—C9—C6	122.86 (16)	S2—C26—H26B	109.5
C11—C10—C9	117.09 (17)	H26A—C26—H26B	109.5
C11—C10—H10	121.5	S2—C26—H26C	109.5
C9—C10—H10	121.5	H26A—C26—H26C	109.5
N4—C11—C10	123.96 (17)	H26B—C26—H26C	109.5
N4—C11—H11	118.0	C7—N1—N2	112.18 (14)
C10—C11—H11	118.0	C7—N1—C3	128.07 (15)
N5—C12—N4	127.39 (18)	N2—N1—C3	119.35 (14)
N5—C12—S1	119.05 (14)	C5—N2—N1	104.46 (14)
N4—C12—S1	113.57 (14)	C7—N3—C8	120.42 (15)
S1—C13—H13A	109.5	C7—N3—H3N	109.2 (17)
S1—C13—H13B	109.5	C8—N3—H3N	113.3 (17)
H13A—C13—H13B	109.5	C12—N4—C11	114.28 (16)
S1—C13—H13C	109.5	C12—N5—C9	117.16 (16)
H13A—C13—H13C	109.5	C20—N6—N7	112.26 (14)
H13B—C13—H13C	109.5	C20—N6—C16	127.71 (15)
O2—C14—C15	105.96 (16)	N7—N6—C16	119.47 (14)
O2—C14—H14A	110.5	C18—N7—N6	104.35 (14)
C15—C14—H14A	110.5	C20—N8—C21	121.13 (15)
O2—C14—H14B	110.5	C20—N8—H8N	107.4 (17)
C15—C14—H14B	110.5	C21—N8—H8N	113.2 (16)
H14A—C14—H14B	108.7	C25—N9—C24	114.62 (16)
C14—C15—C16	102.77 (16)	C25—N10—C22	117.17 (15)
C14—C15—H15A	111.2	C1—O1—C4	105.24 (15)
C16—C15—H15A	111.2	C14—O2—C17	106.04 (16)
C14—C15—H15B	111.2	C12—S1—C13	102.24 (9)
C16—C15—H15B	111.2	C25—S2—C26	102.10 (9)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3N···N5	0.82 (2)	2.16 (2)	2.828 (2)	139 (2)
N8—H8N···N10	0.83 (2)	2.13 (2)	2.820 (2)	140 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3N⋯N5	0.82 (2)	2.16 (2)	2.828 (2)	139 (2)
N8—H8N⋯N10	0.83 (2)	2.13 (2)	2.820 (2)	140 (2)