2-Amino-pyrimidinium picrate.

The geometric parameters of the title compound, C(4)H(6)N(3) (+)·C(6)H(2)N(3)O(7) (-), are in the usual ranges. While two nitro groups are almost coplanar with the aromatic picrate ring [dihedral angles 3.0 (2) and 4.4 (3)°], the third is significantly twisted out of this plane [dihedral angle 46.47 (8)°]. Anions and cations are connected via N-H⋯O hydrogen bonds. The mol-ecules crystallize in planes parallel to (11).

Related literature

For related literature, see: Barraclough & Smith (1995 ▶); Etter et al. (1990 ▶); Fischer et al. (2007 ▶); Goswami et al. (2000 ▶); Gueiffier et al. (1996 ▶); Katritzky et al. (2003 ▶); Rival et al. (1991 ▶); Sanfilippo et al. (1988 ▶); Scheinbeim & Schempp (1976 ▶); Schlueter et al. (2006 ▶); Tully et al. (1991 ▶); Yathirajan, Bindya et al. (2007a ▶,b ▶); Yathirajan, Mayekar et al. (2007 ▶); Yathirajan, Narayana et al. (2007 ▶).

Experimental

Crystal data

C4H6N3 +·C6H2N3O7 −

M = 324.22

Triclinic,

a = 5.8803 (7) Å

b = 8.0025 (10) Å

c = 13.8108 (17) Å

α = 88.021 (10)°

β = 82.322 (9)°

γ = 88.739 (10)°

V = 643.59 (14) Å3

Z = 2

Mo Kα radiation

μ = 0.14 mm−1

T = 173 (2) K

0.26 × 0.22 × 0.09 mm

Data collection

Stoe IPDSII two-circle diffractometer

Absorption correction: none

8757 measured reflections

2402 independent reflections

1927 reflections with I > 2σ(I)

R int = 0.042

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.099

S = 1.01

2402 reflections

220 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.20 e Å−3

Δρmin = −0.27 e Å−3

Data collection: X-AREA (Stoe & Cie, 2001 ▶); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: PLATON (Spek, 2003 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807062599/at2509sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807062599/at2509Isup2.hkl

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

C4H6N3+·C6H2N3O7–	Z = 2
Mr = 324.22	F000 = 332
Triclinic, P1	Dx = 1.673 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 5.8803 (7) Å	Cell parameters from 8213 reflections
b = 8.0025 (10) Å	θ = 3.5–25.8º
c = 13.8108 (17) Å	µ = 0.15 mm−1
α = 88.021 (10)º	T = 173 (2) K
β = 82.322 (9)º	Plate, yellow
γ = 88.739 (10)º	0.26 × 0.22 × 0.09 mm
V = 643.59 (14) Å3

Stoe IPDSII two-circle diffractometer	1927 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.042
Monochromator: graphite	θmax = 25.6º
T = 173(2) K	θmin = 3.5º
ω scans	h = −7→7
Absorption correction: none	k = −9→9
8757 measured reflections	l = −16→16
2402 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)] = 0.036	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.099	w = 1/[σ2(Fo2) + (0.0661P)2] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max < 0.001
2402 reflections	Δρmax = 0.20 e Å−3
220 parameters	Δρmin = −0.27 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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
N1	0.7277 (3)	0.40774 (18)	0.07873 (11)	0.0279 (3)
H1A	0.799 (3)	0.422 (2)	0.0195 (16)	0.033 (5)*
H1B	0.600 (4)	0.346 (3)	0.0984 (15)	0.039 (5)*
C1	0.8282 (3)	0.47463 (18)	0.14768 (11)	0.0199 (3)
N2	0.7333 (2)	0.45943 (15)	0.24319 (9)	0.0206 (3)
H2	0.604 (4)	0.400 (3)	0.2556 (15)	0.039 (5)*
C3	0.8321 (3)	0.52828 (18)	0.31540 (11)	0.0229 (3)
H3	0.7618	0.5183	0.3814	0.027*
C4	1.0334 (3)	0.61214 (19)	0.29261 (11)	0.0241 (3)
H4	1.1076	0.6609	0.3415	0.029*
C5	1.1247 (3)	0.62249 (18)	0.19338 (12)	0.0229 (3)
H5	1.2654	0.6791	0.1762	0.027*
N6	1.0274 (2)	0.55855 (15)	0.12224 (9)	0.0228 (3)
C11	0.2209 (2)	0.17922 (17)	0.24085 (11)	0.0194 (3)
C12	0.0995 (2)	0.17467 (18)	0.33896 (11)	0.0196 (3)
C13	−0.1064 (2)	0.09207 (18)	0.36532 (11)	0.0201 (3)
H13	−0.1809	0.0931	0.4307	0.024*
C14	−0.2010 (2)	0.00844 (17)	0.29461 (11)	0.0197 (3)
C15	−0.0957 (3)	0.00409 (18)	0.19783 (11)	0.0209 (3)
H15	−0.1612	−0.0560	0.1506	0.025*
C16	0.1043 (2)	0.08881 (18)	0.17311 (11)	0.0197 (3)
N11	0.1908 (2)	0.26127 (16)	0.41664 (10)	0.0238 (3)
N12	−0.4142 (2)	−0.08122 (16)	0.32163 (10)	0.0250 (3)
N13	0.2118 (2)	0.08312 (16)	0.07100 (9)	0.0226 (3)
O11	0.41007 (18)	0.24842 (14)	0.21384 (8)	0.0276 (3)
O12	0.3751 (2)	0.33240 (17)	0.39985 (9)	0.0371 (3)
O13	0.0778 (2)	0.2607 (2)	0.49744 (9)	0.0534 (4)
O14	−0.5137 (2)	−0.07121 (17)	0.40512 (9)	0.0396 (3)
O15	−0.4859 (2)	−0.16322 (15)	0.25825 (10)	0.0366 (3)
O16	0.2234 (2)	−0.05385 (14)	0.03198 (9)	0.0323 (3)
O17	0.2799 (2)	0.21390 (15)	0.02874 (9)	0.0334 (3)

	U11	U22	U33	U12	U13	U23
N1	0.0296 (8)	0.0360 (8)	0.0185 (7)	−0.0172 (6)	−0.0015 (6)	−0.0027 (6)
C1	0.0220 (7)	0.0191 (7)	0.0183 (7)	−0.0042 (5)	−0.0013 (6)	−0.0009 (6)
N2	0.0207 (6)	0.0211 (6)	0.0201 (7)	−0.0059 (5)	−0.0014 (5)	−0.0018 (5)
C3	0.0273 (8)	0.0228 (7)	0.0186 (8)	−0.0021 (6)	−0.0026 (6)	−0.0037 (6)
C4	0.0275 (8)	0.0234 (7)	0.0227 (8)	−0.0042 (6)	−0.0063 (6)	−0.0054 (6)
C5	0.0226 (7)	0.0211 (7)	0.0254 (8)	−0.0073 (6)	−0.0034 (6)	−0.0035 (6)
N6	0.0244 (7)	0.0235 (6)	0.0206 (7)	−0.0087 (5)	−0.0015 (5)	−0.0031 (5)
C11	0.0190 (7)	0.0181 (7)	0.0215 (8)	−0.0028 (5)	−0.0030 (6)	−0.0020 (6)
C12	0.0205 (7)	0.0205 (7)	0.0187 (8)	−0.0034 (6)	−0.0049 (6)	−0.0030 (6)
C13	0.0200 (7)	0.0199 (7)	0.0199 (8)	−0.0011 (5)	−0.0007 (6)	0.0001 (6)
C14	0.0158 (7)	0.0179 (7)	0.0255 (8)	−0.0042 (5)	−0.0022 (6)	−0.0012 (6)
C15	0.0221 (7)	0.0193 (7)	0.0226 (8)	−0.0019 (5)	−0.0063 (6)	−0.0048 (6)
C16	0.0208 (7)	0.0208 (7)	0.0176 (8)	−0.0014 (6)	−0.0025 (6)	−0.0018 (6)
N11	0.0244 (7)	0.0276 (7)	0.0196 (7)	−0.0063 (5)	−0.0023 (5)	−0.0039 (5)
N12	0.0193 (6)	0.0241 (6)	0.0316 (8)	−0.0048 (5)	−0.0031 (5)	−0.0008 (6)
N13	0.0212 (6)	0.0270 (7)	0.0201 (7)	−0.0026 (5)	−0.0035 (5)	−0.0052 (5)
O11	0.0226 (6)	0.0368 (6)	0.0233 (6)	−0.0141 (5)	0.0006 (4)	−0.0050 (5)
O12	0.0342 (7)	0.0518 (8)	0.0267 (6)	−0.0260 (6)	−0.0030 (5)	−0.0070 (5)
O13	0.0449 (8)	0.0925 (12)	0.0221 (7)	−0.0335 (7)	0.0095 (6)	−0.0245 (7)
O14	0.0298 (7)	0.0545 (8)	0.0322 (7)	−0.0175 (6)	0.0075 (5)	−0.0038 (6)
O15	0.0306 (6)	0.0386 (7)	0.0425 (8)	−0.0170 (5)	−0.0067 (5)	−0.0107 (6)
O16	0.0375 (7)	0.0321 (6)	0.0272 (6)	−0.0035 (5)	−0.0006 (5)	−0.0137 (5)
O17	0.0422 (7)	0.0339 (6)	0.0227 (6)	−0.0089 (5)	0.0017 (5)	0.0014 (5)

N1—C1	1.320 (2)	C12—C13	1.392 (2)
N1—H1A	0.87 (2)	C12—N11	1.4631 (19)
N1—H1B	0.91 (2)	C13—C14	1.385 (2)
C1—N6	1.3622 (19)	C13—H13	0.9500
C1—N2	1.3643 (19)	C14—C15	1.397 (2)
N2—C3	1.3572 (19)	C14—N12	1.4568 (18)
N2—H2	0.90 (2)	C15—C16	1.368 (2)
C3—C4	1.368 (2)	C15—H15	0.9500
C3—H3	0.9500	C16—N13	1.4682 (19)
C4—C5	1.404 (2)	N11—O13	1.2202 (18)
C4—H4	0.9500	N11—O12	1.2262 (17)
C5—N6	1.324 (2)	N12—O14	1.2258 (18)
C5—H5	0.9500	N12—O15	1.2349 (17)
C11—O11	1.2588 (18)	N13—O17	1.2289 (17)
C11—C12	1.444 (2)	N13—O16	1.2345 (17)
C11—C16	1.452 (2)
C1—N1—H1A	115.1 (13)	C13—C12—N11	116.45 (13)
C1—N1—H1B	117.1 (13)	C11—C12—N11	120.10 (12)
H1A—N1—H1B	127.5 (19)	C14—C13—C12	118.89 (14)
N1—C1—N6	119.19 (14)	C14—C13—H13	120.6
N1—C1—N2	120.24 (13)	C12—C13—H13	120.6
N6—C1—N2	120.57 (13)	C13—C14—C15	122.04 (13)
C3—N2—C1	121.42 (13)	C13—C14—N12	119.44 (14)
C3—N2—H2	122.1 (13)	C15—C14—N12	118.50 (13)
C1—N2—H2	116.5 (13)	C16—C15—C14	118.09 (13)
N2—C3—C4	119.58 (14)	C16—C15—H15	121.0
N2—C3—H3	120.2	C14—C15—H15	121.0
C4—C3—H3	120.2	C15—C16—C11	124.88 (14)
C3—C4—C5	116.62 (14)	C15—C16—N13	117.24 (13)
C3—C4—H4	121.7	C11—C16—N13	117.85 (12)
C5—C4—H4	121.7	O13—N11—O12	121.68 (13)
N6—C5—C4	124.25 (14)	O13—N11—C12	118.02 (12)
N6—C5—H5	117.9	O12—N11—C12	120.30 (13)
C4—C5—H5	117.9	O14—N12—O15	123.36 (13)
C5—N6—C1	117.53 (13)	O14—N12—C14	118.93 (13)
O11—C11—C12	125.89 (13)	O15—N12—C14	117.70 (13)
O11—C11—C16	121.46 (13)	O17—N13—O16	123.85 (13)
C12—C11—C16	112.63 (13)	O17—N13—C16	118.75 (12)
C13—C12—C11	123.45 (13)	O16—N13—C16	117.38 (12)
N1—C1—N2—C3	−179.40 (14)	C14—C15—C16—C11	2.1 (2)
N6—C1—N2—C3	0.7 (2)	C14—C15—C16—N13	−179.82 (13)
C1—N2—C3—C4	−1.3 (2)	O11—C11—C16—C15	176.85 (14)
N2—C3—C4—C5	0.6 (2)	C12—C11—C16—C15	−1.5 (2)
C3—C4—C5—N6	0.7 (2)	O11—C11—C16—N13	−1.2 (2)
C4—C5—N6—C1	−1.3 (2)	C12—C11—C16—N13	−179.53 (12)
N1—C1—N6—C5	−179.32 (15)	C13—C12—N11—O13	−2.7 (2)
N2—C1—N6—C5	0.6 (2)	C11—C12—N11—O13	176.73 (15)
O11—C11—C12—C13	−178.11 (14)	C13—C12—N11—O12	177.68 (14)
C16—C11—C12—C13	0.2 (2)	C11—C12—N11—O12	−2.9 (2)
O11—C11—C12—N11	2.5 (2)	C13—C14—N12—O14	4.9 (2)
C16—C11—C12—N11	−179.19 (12)	C15—C14—N12—O14	−176.38 (14)
C11—C12—C13—C14	0.4 (2)	C13—C14—N12—O15	−175.46 (14)
N11—C12—C13—C14	179.81 (13)	C15—C14—N12—O15	3.2 (2)
C12—C13—C14—C15	0.2 (2)	C15—C16—N13—O17	133.79 (15)
C12—C13—C14—N12	178.82 (13)	C11—C16—N13—O17	−48.03 (19)
C13—C14—C15—C16	−1.4 (2)	C15—C16—N13—O16	−44.61 (19)
N12—C14—C15—C16	179.93 (13)	C11—C16—N13—O16	133.57 (14)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···N6i	0.87 (2)	2.09 (2)	2.958 (2)	177.0 (18)
N1—H1B···O11	0.91 (2)	1.97 (2)	2.7577 (19)	143.7 (18)
N1—H1B···O17	0.91 (2)	2.50 (2)	3.2488 (18)	140.0 (17)
N2—H2···O11	0.90 (2)	1.84 (2)	2.6501 (16)	148.6 (19)
N2—H2···O12	0.90 (2)	2.31 (2)	2.9792 (18)	131.6 (17)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯N6i	0.87 (2)	2.09 (2)	2.958 (2)	177.0 (18)
N1—H1B⋯O11	0.91 (2)	1.97 (2)	2.7577 (19)	143.7 (18)
N1—H1B⋯O17	0.91 (2)	2.50 (2)	3.2488 (18)	140.0 (17)
N2—H2⋯O11	0.90 (2)	1.84 (2)	2.6501 (16)	148.6 (19)
N2—H2⋯O12	0.90 (2)	2.31 (2)	2.9792 (18)	131.6 (17)

Symmetry code: (i) .