N'-[1-(4-Amino-phen-yl)ethyl]pyrazine-2-carbohydrazide.

The title compound, C(13)H(13)N(5)O, crystallizes with two mol-ecules in the asymmetric unit. The crystal structure is stabilized by intra-molecular N-H⋯N and N-H⋯O hydrogen bonds. The dihedral angles between the pyrazine ring and the 4-aminolphenyl ring are 2.5 (1) and 6.5 (1)° in the two molecules.

Related literature

For applications of the pyrazine ring system in drug development, see: Du et al. (2009 ▶); Dubinina et al. (2006 ▶); Ellsworth et al. (2007 ▶); Mukaiyama et al. (2007 ▶).

Experimental

Crystal data

C13H13N5O

M = 255.28

Triclinic,

a = 6.9783 (13) Å

b = 10.689 (3) Å

c = 17.061 (5) Å

α = 106.971 (10)°

β = 98.499 (4)°

γ = 90.174 (14)°

V = 1202.3 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 113 K

0.10 × 0.09 × 0.04 mm

Data collection

Rigaku Saturn diffractometer

Absorption correction: multi-scan (REQAB; Jacobson, 1998 ▶) T min = 0.991, T max = 0.996

9090 measured reflections

4150 independent reflections

2832 reflections with I > 2σ(I)

R int = 0.052

Refinement

R[F 2 > 2σ(F 2)] = 0.069

wR(F 2) = 0.164

S = 1.05

4150 reflections

364 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.26 e Å−3

Δρmin = −0.30 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku/MSC, 2005 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810004083/hg2638sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810004083/hg2638Isup2.hkl

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

C13H13N5O	Z = 4
Mr = 255.28	F(000) = 536
Triclinic, P1	Dx = 1.410 Mg m−3
a = 6.9783 (13) Å	Mo Kα radiation, λ = 0.71070 Å
b = 10.689 (3) Å	Cell parameters from 2002 reflections
c = 17.061 (5) Å	θ = 2.5–27.8°
α = 106.971 (10)°	µ = 0.10 mm−1
β = 98.499 (4)°	T = 113 K
γ = 90.174 (14)°	Platelet, yellow
V = 1202.3 (5) Å3	0.10 × 0.09 × 0.04 mm

Rigaku Saturn diffractometer	4150 independent reflections
Radiation source: rotating anode	2832 reflections with I > 2σ(I)
confocal	Rint = 0.052
Detector resolution: 7.31 pixels mm-1	θmax = 25.0°, θmin = 2.0°
ω scans	h = −8→8
Absorption correction: multi-scan (REQAB; Jacobson, 1998)	k = −11→12
Tmin = 0.991, Tmax = 0.996	l = −20→20
9090 measured reflections

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)] = 0.069	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.164	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0724P)2] where P = (Fo2 + 2Fc2)/3
4150 reflections	(Δ/σ)max = 0.001
364 parameters	Δρmax = 0.26 e Å−3
0 restraints	Δρmin = −0.29 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	0.8650 (4)	0.1637 (3)	0.24329 (16)	0.0213 (6)
C2	0.8881 (4)	0.0891 (3)	0.16283 (16)	0.0243 (7)
H2	0.9195	−0.0001	0.1527	0.029*
C3	0.8657 (4)	0.1438 (3)	0.09828 (17)	0.0220 (6)
H3	0.8823	0.0913	0.0445	0.026*
C4	0.8193 (4)	0.2747 (3)	0.11007 (16)	0.0197 (6)
C5	0.7963 (4)	0.3486 (3)	0.19089 (16)	0.0220 (6)
H5	0.7631	0.4375	0.2009	0.026*
C6	0.8207 (4)	0.2952 (3)	0.25550 (17)	0.0239 (7)
H6	0.8074	0.3483	0.3096	0.029*
C7	0.7939 (4)	0.3348 (3)	0.04141 (16)	0.0217 (6)
C8	0.8024 (4)	0.2514 (3)	−0.04611 (16)	0.0289 (7)
H8A	0.7298	0.2917	−0.0854	0.043*
H8B	0.7451	0.1638	−0.0546	0.043*
H8C	0.9379	0.2447	−0.0552	0.043*
C9	0.6961 (4)	0.6487 (3)	0.02186 (16)	0.0217 (6)
C10	0.6788 (4)	0.7066 (3)	−0.04848 (16)	0.0203 (6)
C11	0.6397 (4)	0.8372 (3)	−0.03596 (17)	0.0238 (7)
H11	0.6214	0.8884	0.0179	0.029*
C12	0.6529 (4)	0.8158 (3)	−0.17048 (17)	0.0268 (7)
H12	0.6445	0.8509	−0.2159	0.032*
C13	0.6926 (4)	0.6840 (3)	−0.18385 (17)	0.0256 (7)
H13	0.7104	0.6328	−0.2378	0.031*
C14	0.4201 (4)	0.1709 (3)	0.68980 (17)	0.0227 (6)
C15	0.3869 (4)	0.0943 (3)	0.60680 (17)	0.0256 (7)
H15	0.3857	0.0016	0.5936	0.031*
C16	0.3557 (4)	0.1525 (3)	0.54366 (17)	0.0249 (7)
H16	0.3359	0.0986	0.4877	0.030*
C17	0.3526 (4)	0.2884 (3)	0.56009 (16)	0.0221 (6)
C18	0.3846 (4)	0.3637 (3)	0.64354 (17)	0.0246 (7)
H18	0.3836	0.4564	0.6569	0.029*
C19	0.4175 (4)	0.3068 (3)	0.70710 (17)	0.0250 (7)
H19	0.4386	0.3606	0.7631	0.030*
C20	0.3116 (4)	0.3502 (3)	0.49280 (16)	0.0222 (6)
C21	0.3380 (4)	0.2769 (3)	0.40568 (17)	0.0299 (7)
H21A	0.2126	0.2644	0.3692	0.045*
H21B	0.3896	0.1913	0.4046	0.045*
H21C	0.4289	0.3271	0.3865	0.045*
C22	0.1804 (4)	0.6521 (3)	0.46356 (17)	0.0242 (7)
C23	0.1331 (4)	0.6910 (3)	0.38597 (16)	0.0214 (6)
C24	0.1030 (4)	0.8204 (3)	0.38957 (17)	0.0261 (7)
H24	0.1126	0.8839	0.4424	0.031*
C25	0.0467 (4)	0.7651 (3)	0.24967 (17)	0.0262 (7)
H25	0.0152	0.7878	0.1996	0.031*
C26	0.0763 (4)	0.6349 (3)	0.24498 (17)	0.0265 (7)
H26	0.0644	0.5714	0.1921	0.032*
N1	0.8761 (4)	0.1101 (2)	0.30779 (15)	0.0294 (6)
H1A	0.933 (5)	0.036 (3)	0.3056 (18)	0.044*
H1B	0.861 (4)	0.171 (3)	0.361 (2)	0.044*
N2	0.7625 (3)	0.4591 (2)	0.06300 (13)	0.0228 (5)
N3	0.7388 (3)	0.5209 (2)	0.00192 (14)	0.0224 (6)
H3A	0.742 (4)	0.482 (3)	−0.0522 (17)	0.027*
N4	0.7064 (3)	0.6282 (2)	−0.12325 (13)	0.0228 (5)
N5	0.6263 (3)	0.8945 (2)	−0.09690 (14)	0.0264 (6)
N6	0.4577 (4)	0.1131 (3)	0.75362 (16)	0.0289 (6)
H6A	0.410 (5)	0.029 (3)	0.7404 (18)	0.043*
H6B	0.433 (4)	0.168 (3)	0.8058 (19)	0.043*
N7	0.2571 (3)	0.4699 (2)	0.51400 (14)	0.0257 (6)
N8	0.2176 (3)	0.5256 (2)	0.44979 (14)	0.0238 (6)
H8	0.198 (4)	0.475 (3)	0.3982 (17)	0.029*
N9	0.1215 (3)	0.5968 (2)	0.31366 (14)	0.0257 (6)
N10	0.0608 (3)	0.8597 (2)	0.32169 (14)	0.0277 (6)
O1	0.6759 (3)	0.71548 (19)	0.09187 (12)	0.0328 (5)
O2	0.1874 (3)	0.73296 (19)	0.53239 (11)	0.0347 (5)

	U11	U22	U33	U12	U13	U23
C1	0.0209 (14)	0.0198 (15)	0.0229 (16)	−0.0025 (11)	−0.0002 (11)	0.0074 (12)
C2	0.0294 (15)	0.0212 (16)	0.0211 (16)	0.0025 (12)	0.0050 (12)	0.0038 (12)
C3	0.0214 (14)	0.0227 (16)	0.0206 (15)	0.0012 (12)	0.0036 (11)	0.0044 (12)
C4	0.0185 (13)	0.0181 (15)	0.0241 (16)	−0.0013 (11)	0.0033 (11)	0.0086 (12)
C5	0.0218 (14)	0.0180 (15)	0.0263 (16)	0.0008 (11)	0.0031 (12)	0.0069 (12)
C6	0.0284 (15)	0.0227 (16)	0.0204 (15)	0.0025 (12)	0.0053 (12)	0.0050 (12)
C7	0.0167 (13)	0.0245 (16)	0.0220 (15)	−0.0024 (11)	0.0026 (11)	0.0042 (12)
C8	0.0337 (16)	0.0316 (18)	0.0224 (16)	0.0013 (13)	0.0044 (13)	0.0092 (13)
C9	0.0239 (14)	0.0208 (16)	0.0204 (16)	−0.0003 (12)	0.0022 (12)	0.0066 (12)
C10	0.0170 (13)	0.0212 (15)	0.0221 (15)	0.0008 (11)	0.0043 (11)	0.0048 (12)
C11	0.0236 (15)	0.0249 (16)	0.0221 (16)	−0.0021 (12)	0.0019 (12)	0.0064 (13)
C12	0.0265 (15)	0.0317 (18)	0.0258 (17)	0.0006 (13)	0.0026 (12)	0.0147 (14)
C13	0.0255 (15)	0.0332 (18)	0.0192 (15)	0.0011 (13)	0.0047 (12)	0.0088 (13)
C14	0.0199 (14)	0.0238 (16)	0.0262 (16)	0.0032 (12)	0.0066 (12)	0.0087 (13)
C15	0.0293 (16)	0.0211 (16)	0.0287 (17)	0.0026 (12)	0.0099 (13)	0.0082 (13)
C16	0.0292 (15)	0.0238 (16)	0.0215 (16)	0.0011 (12)	0.0067 (12)	0.0050 (12)
C17	0.0195 (14)	0.0248 (16)	0.0219 (15)	0.0026 (12)	0.0046 (11)	0.0063 (12)
C18	0.0248 (15)	0.0216 (16)	0.0267 (16)	0.0031 (12)	0.0020 (12)	0.0071 (13)
C19	0.0222 (14)	0.0301 (17)	0.0205 (15)	−0.0007 (12)	0.0022 (12)	0.0043 (13)
C20	0.0194 (14)	0.0277 (17)	0.0197 (15)	−0.0007 (12)	0.0040 (11)	0.0069 (13)
C21	0.0376 (17)	0.0279 (17)	0.0244 (17)	0.0056 (13)	0.0060 (13)	0.0074 (13)
C22	0.0219 (14)	0.0234 (16)	0.0265 (17)	−0.0014 (12)	0.0035 (12)	0.0061 (13)
C23	0.0207 (14)	0.0235 (16)	0.0198 (15)	−0.0002 (12)	0.0049 (11)	0.0053 (12)
C24	0.0303 (16)	0.0268 (17)	0.0211 (16)	0.0037 (13)	0.0058 (12)	0.0060 (13)
C25	0.0258 (15)	0.0317 (18)	0.0235 (16)	0.0078 (13)	0.0043 (12)	0.0113 (14)
C26	0.0269 (15)	0.0300 (17)	0.0203 (16)	0.0018 (13)	0.0050 (12)	0.0036 (13)
N1	0.0450 (16)	0.0207 (15)	0.0250 (14)	0.0080 (12)	0.0097 (12)	0.0087 (12)
N2	0.0246 (13)	0.0237 (14)	0.0217 (13)	0.0013 (10)	0.0013 (10)	0.0103 (11)
N3	0.0290 (13)	0.0224 (14)	0.0166 (13)	0.0012 (10)	0.0036 (10)	0.0073 (11)
N4	0.0238 (12)	0.0244 (13)	0.0203 (13)	0.0017 (10)	0.0044 (10)	0.0064 (10)
N5	0.0277 (13)	0.0249 (14)	0.0292 (14)	−0.0004 (10)	0.0057 (10)	0.0116 (11)
N6	0.0358 (15)	0.0285 (15)	0.0267 (15)	0.0041 (12)	0.0074 (11)	0.0135 (12)
N7	0.0305 (13)	0.0272 (14)	0.0224 (13)	0.0024 (11)	0.0057 (10)	0.0110 (11)
N8	0.0300 (13)	0.0231 (14)	0.0176 (13)	0.0013 (10)	0.0028 (10)	0.0055 (11)
N9	0.0250 (12)	0.0284 (14)	0.0227 (13)	0.0024 (10)	0.0033 (10)	0.0062 (11)
N10	0.0305 (13)	0.0252 (14)	0.0289 (14)	0.0031 (11)	0.0058 (11)	0.0096 (11)
O1	0.0459 (13)	0.0313 (12)	0.0214 (12)	0.0075 (10)	0.0080 (9)	0.0068 (9)
O2	0.0509 (14)	0.0298 (12)	0.0199 (12)	0.0042 (10)	0.0042 (9)	0.0027 (9)

C1—N1	1.374 (3)	C15—H15	0.9500
C1—C6	1.402 (4)	C16—C17	1.398 (4)
C1—C2	1.405 (3)	C16—H16	0.9500
C2—C3	1.380 (4)	C17—C18	1.400 (4)
C2—H2	0.9500	C17—C20	1.477 (4)
C3—C4	1.400 (3)	C18—C19	1.383 (4)
C3—H3	0.9500	C18—H18	0.9500
C4—C5	1.408 (4)	C19—H19	0.9500
C4—C7	1.481 (4)	C20—N7	1.298 (3)
C5—C6	1.372 (4)	C20—C21	1.503 (4)
C5—H5	0.9500	C21—H21A	0.9800
C6—H6	0.9500	C21—H21B	0.9800
C7—N2	1.300 (3)	C21—H21C	0.9800
C7—C8	1.509 (4)	C22—O2	1.232 (3)
C8—H8A	0.9800	C22—N8	1.336 (3)
C8—H8B	0.9800	C22—C23	1.493 (4)
C8—H8C	0.9800	C23—N9	1.337 (3)
C9—O1	1.228 (3)	C23—C24	1.385 (4)
C9—N3	1.353 (3)	C24—N10	1.337 (3)
C9—C10	1.493 (4)	C24—H24	0.9500
C10—N4	1.348 (3)	C25—N10	1.334 (3)
C10—C11	1.383 (4)	C25—C26	1.388 (4)
C11—N5	1.345 (3)	C25—H25	0.9500
C11—H11	0.9500	C26—N9	1.345 (3)
C12—N5	1.331 (3)	C26—H26	0.9500
C12—C13	1.395 (4)	N1—H1A	0.88 (3)
C12—H12	0.9500	N1—H1B	0.97 (3)
C13—N4	1.329 (3)	N2—N3	1.379 (3)
C13—H13	0.9500	N3—H3A	0.90 (3)
C14—N6	1.394 (4)	N6—H6A	0.91 (3)
C14—C19	1.396 (4)	N6—H6B	0.95 (3)
C14—C15	1.398 (4)	N7—N8	1.387 (3)
C15—C16	1.384 (4)	N8—H8	0.88 (3)
N1—C1—C6	120.2 (2)	C16—C17—C18	117.0 (2)
N1—C1—C2	122.1 (3)	C16—C17—C20	121.7 (2)
C6—C1—C2	117.6 (2)	C18—C17—C20	121.3 (3)
C3—C2—C1	120.8 (3)	C19—C18—C17	121.8 (3)
C3—C2—H2	119.6	C19—C18—H18	119.1
C1—C2—H2	119.6	C17—C18—H18	119.1
C2—C3—C4	121.7 (2)	C18—C19—C14	120.6 (3)
C2—C3—H3	119.1	C18—C19—H19	119.7
C4—C3—H3	119.1	C14—C19—H19	119.7
C3—C4—C5	117.1 (2)	N7—C20—C17	116.3 (2)
C3—C4—C7	122.4 (2)	N7—C20—C21	123.2 (2)
C5—C4—C7	120.5 (2)	C17—C20—C21	120.5 (2)
C6—C5—C4	121.4 (3)	C20—C21—H21A	109.5
C6—C5—H5	119.3	C20—C21—H21B	109.5
C4—C5—H5	119.3	H21A—C21—H21B	109.5
C5—C6—C1	121.3 (3)	C20—C21—H21C	109.5
C5—C6—H6	119.3	H21A—C21—H21C	109.5
C1—C6—H6	119.3	H21B—C21—H21C	109.5
N2—C7—C4	115.2 (2)	O2—C22—N8	125.4 (3)
N2—C7—C8	125.0 (2)	O2—C22—C23	121.2 (3)
C4—C7—C8	119.8 (2)	N8—C22—C23	113.5 (2)
C7—C8—H8A	109.5	N9—C23—C24	121.7 (2)
C7—C8—H8B	109.5	N9—C23—C22	117.6 (2)
H8A—C8—H8B	109.5	C24—C23—C22	120.7 (2)
C7—C8—H8C	109.5	N10—C24—C23	122.7 (3)
H8A—C8—H8C	109.5	N10—C24—H24	118.7
H8B—C8—H8C	109.5	C23—C24—H24	118.7
O1—C9—N3	124.3 (3)	N10—C25—C26	122.6 (3)
O1—C9—C10	121.0 (2)	N10—C25—H25	118.7
N3—C9—C10	114.7 (2)	C26—C25—H25	118.7
N4—C10—C11	121.8 (2)	N9—C26—C25	121.5 (2)
N4—C10—C9	117.7 (2)	N9—C26—H26	119.3
C11—C10—C9	120.5 (2)	C25—C26—H26	119.3
N5—C11—C10	122.7 (3)	C1—N1—H1A	121 (2)
N5—C11—H11	118.6	C1—N1—H1B	114.9 (18)
C10—C11—H11	118.6	H1A—N1—H1B	120 (3)
N5—C12—C13	122.9 (3)	C7—N2—N3	117.9 (2)
N5—C12—H12	118.5	C9—N3—N2	119.2 (2)
C13—C12—H12	118.5	C9—N3—H3A	115.6 (17)
N4—C13—C12	121.9 (3)	N2—N3—H3A	125.0 (17)
N4—C13—H13	119.1	C13—N4—C10	115.8 (2)
C12—C13—H13	119.1	C12—N5—C11	114.9 (2)
N6—C14—C19	120.8 (3)	C14—N6—H6A	114.6 (19)
N6—C14—C15	120.9 (3)	C14—N6—H6B	113.5 (18)
C19—C14—C15	118.3 (2)	H6A—N6—H6B	114 (3)
C16—C15—C14	120.6 (3)	C20—N7—N8	115.4 (2)
C16—C15—H15	119.7	C22—N8—N7	121.9 (2)
C14—C15—H15	119.7	C22—N8—H8	117.4 (18)
C15—C16—C17	121.7 (3)	N7—N8—H8	119.9 (18)
C15—C16—H16	119.1	C23—N9—C26	116.1 (2)
C17—C16—H16	119.1	C25—N10—C24	115.4 (2)
N1—C1—C2—C3	176.4 (2)	C16—C17—C20—N7	160.7 (2)
C6—C1—C2—C3	−0.7 (4)	C18—C17—C20—N7	−17.4 (4)
C1—C2—C3—C4	−0.1 (4)	C16—C17—C20—C21	−20.8 (4)
C2—C3—C4—C5	0.1 (4)	C18—C17—C20—C21	161.1 (3)
C2—C3—C4—C7	−179.7 (2)	O2—C22—C23—N9	−177.7 (2)
C3—C4—C5—C6	0.8 (4)	N8—C22—C23—N9	4.0 (3)
C7—C4—C5—C6	−179.4 (2)	O2—C22—C23—C24	2.5 (4)
C4—C5—C6—C1	−1.6 (4)	N8—C22—C23—C24	−175.9 (2)
N1—C1—C6—C5	−175.7 (2)	N9—C23—C24—N10	0.0 (4)
C2—C1—C6—C5	1.5 (4)	C22—C23—C24—N10	179.8 (2)
C3—C4—C7—N2	−176.1 (2)	N10—C25—C26—N9	−0.1 (4)
C5—C4—C7—N2	4.2 (3)	C4—C7—N2—N3	179.6 (2)
C3—C4—C7—C8	4.9 (4)	C8—C7—N2—N3	−1.4 (4)
C5—C4—C7—C8	−174.9 (2)	O1—C9—N3—N2	−0.1 (4)
O1—C9—C10—N4	178.8 (2)	C10—C9—N3—N2	178.5 (2)
N3—C9—C10—N4	0.1 (3)	C7—N2—N3—C9	176.7 (2)
O1—C9—C10—C11	0.0 (4)	C12—C13—N4—C10	0.2 (4)
N3—C9—C10—C11	−178.6 (2)	C11—C10—N4—C13	−0.3 (4)
N4—C10—C11—N5	0.0 (4)	C9—C10—N4—C13	−179.0 (2)
C9—C10—C11—N5	178.7 (2)	C13—C12—N5—C11	−0.3 (4)
N5—C12—C13—N4	0.1 (4)	C10—C11—N5—C12	0.3 (4)
N6—C14—C15—C16	−178.0 (2)	C17—C20—N7—N8	−179.4 (2)
C19—C14—C15—C16	1.1 (4)	C21—C20—N7—N8	2.1 (4)
C14—C15—C16—C17	−1.2 (4)	O2—C22—N8—N7	4.3 (4)
C15—C16—C17—C18	0.7 (4)	C23—C22—N8—N7	−177.4 (2)
C15—C16—C17—C20	−177.5 (2)	C20—N7—N8—C22	−172.7 (2)
C16—C17—C18—C19	−0.1 (4)	C24—C23—N9—C26	−0.9 (4)
C20—C17—C18—C19	178.1 (2)	C22—C23—N9—C26	179.2 (2)
C17—C18—C19—C14	0.1 (4)	C25—C26—N9—C23	1.0 (4)
N6—C14—C19—C18	178.5 (2)	C26—C25—N10—C24	−0.9 (4)
C15—C14—C19—C18	−0.6 (4)	C23—C24—N10—C25	0.9 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···N10i	0.88 (3)	2.16 (3)	3.030 (4)	170 (3)
N1—H1B···O2ii	0.97 (3)	1.89 (3)	2.852 (3)	171 (3)
N6—H6A···N1iii	0.91 (3)	2.38 (3)	3.162 (4)	145 (3)
N6—H6B···O1ii	0.95 (3)	2.07 (3)	3.015 (3)	169 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯N10i	0.88 (3)	2.16 (3)	3.030 (4)	170 (3)
N1—H1B⋯O2ii	0.97 (3)	1.89 (3)	2.852 (3)	171 (3)
N6—H6A⋯N1iii	0.91 (3)	2.38 (3)	3.162 (4)	145 (3)
N6—H6B⋯O1ii	0.95 (3)	2.07 (3)	3.015 (3)	169 (3)

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