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Acta Crystallogr Sect E Struct Rep Online. 2010 January 1; 66(Pt 1): o127.
Published online 2009 December 12. doi:  10.1107/S1600536809052362
PMCID: PMC2980124

2-Amino­pyrimidinium nitrate

Abstract

In the title compound, C4H6N3 +·NO3 , the cation is coplanar with the anion (r.m.s. deviation = 0.048 Å), and links to the anion via an N—H(...)O hydrogen bond, forming an ion pair. In the crystal, adjacent ion pairs are further linked by N—H(...)O hydrogen bonds into linear chains running along the b axis.

Related literature

For the crystal structures of the 2-amino­pyrimidinium salts of other mineral acids, see: Czupiński et al. (2005 [triangle]); Lee et al. (2003 [triangle]); Ye et al. (2002 [triangle]).

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Object name is e-66-0o127-scheme1.jpg

Experimental

Crystal data

  • C4H6N3 +·NO3
  • M r = 158.13
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-0o127-efi1.jpg
  • a = 12.632 (2) Å
  • b = 6.2160 (8) Å
  • c = 17.727 (2) Å
  • β = 99.009 (3)°
  • V = 1374.8 (3) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.13 mm−1
  • T = 293 K
  • 0.25 × 0.20 × 0.15 mm

Data collection

  • Rigaku R-AXIS RAPID IP diffractometer
  • Absorption correction: multi-scan (ABSCOR; Higashi, 1995 [triangle]) T min = 0.968, T max = 0.981
  • 5139 measured reflections
  • 1210 independent reflections
  • 823 reflections with I > 2σ(I)
  • R int = 0.028

Refinement

  • R[F 2 > 2σ(F 2)] = 0.039
  • wR(F 2) = 0.120
  • S = 0.99
  • 1210 reflections
  • 124 parameters
  • 6 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.19 e Å−3
  • Δρmin = −0.15 e Å−3

Data collection: RAPID-AUTO (Rigaku, 1998 [triangle]); cell refinement: RAPID-AUTO; data reduction: CrystalClear (Rigaku/MSC, 2002 [triangle]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2009 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809052362/xu2705sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809052362/xu2705Isup2.hkl

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

Acknowledgments

We thank the Key Project of the Natural Science Foundation of Heilongjiang Province (No. ZD200903), the Scientific Fund of Remarkable Teachers of Heilongjiang Province (No. 1054 G036), Heilongjiang University and the University of Malaya for supporting this study.

supplementary crystallographic information

Experimental

To an aqueous solution of 2-aminopyrimidine (0.19 g, 2 mmol) was added chromium nitrate nonahydrate (0.80 g, 2 mmol). The pale green solution was set aside for several days. Colorless crystals of the organic salt were isolated.

Refinement

Carbon-bound H-atoms generated geometrically [C–H 0.93 Å, U(H) 1.2Ueq(C)]. The nitrogen-bound H-atoms were refined with a distance restraint of N–H 0.86±0.01 Å; their temperature factors were refined.

Figures

Fig. 1.
Thermal ellipsoid plot (Barbour, 2001) of [C4H6N4][NO3] at the 50% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

Crystal data

C4H6N3+·NO3F(000) = 656
Mr = 158.13Dx = 1.528 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 3773 reflections
a = 12.632 (2) Åθ = 3.3–27.5°
b = 6.2160 (8) ŵ = 0.13 mm1
c = 17.727 (2) ÅT = 293 K
β = 99.009 (3)°Prism, colorless
V = 1374.8 (3) Å30.25 × 0.20 × 0.15 mm
Z = 8

Data collection

Rigaku R-AXIS RAPID IP diffractometer1210 independent reflections
Radiation source: fine-focus sealed tube823 reflections with I > 2σ(I)
graphiteRint = 0.028
ω scanθmax = 25.0°, θmin = 3.3°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)h = −14→14
Tmin = 0.968, Tmax = 0.981k = −7→7
5139 measured reflectionsl = −21→20

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.120H atoms treated by a mixture of independent and constrained refinement
S = 0.99w = 1/[σ2(Fo2) + (0.0773P)2] where P = (Fo2 + 2Fc2)/3
1210 reflections(Δ/σ)max = 0.001
124 parametersΔρmax = 0.19 e Å3
6 restraintsΔρmin = −0.15 e Å3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
O10.61627 (16)1.0844 (3)0.47003 (8)0.0892 (6)
O20.63012 (12)1.3264 (2)0.38605 (8)0.0711 (5)
O30.61420 (14)0.9926 (3)0.35358 (9)0.0797 (5)
N10.62478 (13)0.3594 (3)0.59174 (10)0.0568 (5)
N20.62700 (13)0.7155 (3)0.63460 (9)0.0575 (5)
N30.62544 (15)0.6380 (3)0.50731 (10)0.0633 (5)
N40.62009 (13)1.1341 (3)0.40181 (9)0.0560 (5)
C10.62639 (15)0.5716 (3)0.57800 (10)0.0501 (5)
C20.62721 (17)0.6376 (4)0.70374 (12)0.0616 (6)
C30.62702 (18)0.4200 (4)0.72104 (13)0.0669 (6)
C40.62560 (17)0.2810 (4)0.66282 (13)0.0638 (6)
H10.6222 (17)0.268 (3)0.5539 (10)0.074 (7)*
H110.6213 (19)0.7733 (19)0.4964 (16)0.083 (8)*
H120.6282 (16)0.547 (3)0.4718 (9)0.068 (7)*
H20.6222 (18)0.749 (3)0.7401 (13)0.079 (7)*
H30.628 (2)0.378 (4)0.7724 (10)0.087 (7)*
H40.6234 (17)0.130 (3)0.6655 (12)0.068 (6)*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.1669 (17)0.0547 (10)0.0505 (9)0.0094 (10)0.0311 (9)0.0031 (7)
O20.1061 (12)0.0523 (10)0.0576 (9)−0.0043 (8)0.0217 (8)0.0025 (7)
O30.1178 (13)0.0620 (11)0.0620 (9)−0.0010 (9)0.0227 (8)−0.0182 (8)
N10.0695 (11)0.0435 (11)0.0575 (10)0.0026 (7)0.0104 (8)−0.0033 (8)
N20.0713 (11)0.0478 (10)0.0543 (9)0.0030 (8)0.0126 (8)−0.0039 (8)
N30.0928 (13)0.0486 (13)0.0504 (10)0.0032 (9)0.0174 (9)−0.0014 (8)
N40.0677 (10)0.0512 (11)0.0506 (10)0.0046 (8)0.0144 (8)−0.0020 (8)
C10.0535 (11)0.0447 (12)0.0520 (10)0.0022 (8)0.0077 (8)−0.0022 (8)
C20.0742 (14)0.0584 (15)0.0533 (12)0.0030 (10)0.0131 (10)−0.0047 (10)
C30.0787 (15)0.0674 (15)0.0559 (12)0.0022 (11)0.0146 (11)0.0062 (12)
C40.0736 (14)0.0500 (14)0.0676 (13)0.0011 (10)0.0104 (11)0.0089 (11)

Geometric parameters (Å, °)

O1—N41.257 (2)N3—C11.318 (3)
O2—N41.239 (2)N3—H110.86 (1)
O3—N41.221 (2)N3—H120.85 (1)
N1—C11.342 (2)C2—C31.387 (3)
N1—C41.350 (3)C2—H20.953 (16)
N1—H10.87 (1)C3—C41.344 (3)
N2—C21.318 (3)C3—H30.944 (17)
N2—C11.344 (2)C4—H40.942 (16)
C1—N1—C4121.76 (19)N3—C1—N2119.96 (19)
C1—N1—H1119.8 (16)N1—C1—N2121.17 (18)
C4—N1—H1118.4 (17)N2—C2—C3124.4 (2)
C2—N2—C1116.65 (18)N2—C2—H2111.8 (15)
C1—N3—H11120.6 (19)C3—C2—H2123.6 (15)
C1—N3—H12120.0 (16)C4—C3—C2117.2 (2)
H11—N3—H12119 (3)C4—C3—H3123.9 (16)
O3—N4—O2122.31 (17)C2—C3—H3118.9 (15)
O3—N4—O1119.30 (18)C3—C4—N1118.8 (2)
O2—N4—O1118.39 (16)C3—C4—H4126.9 (13)
N3—C1—N1118.86 (18)N1—C4—H4114.3 (13)
C4—N1—C1—N3−179.98 (18)C1—N2—C2—C30.1 (3)
C4—N1—C1—N2−1.2 (3)N2—C2—C3—C4−0.6 (3)
C2—N2—C1—N3179.55 (19)C2—C3—C4—N10.2 (3)
C2—N2—C1—N10.8 (3)C1—N1—C4—C30.6 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1···O1i0.87 (1)1.87 (1)2.742 (2)177 (2)
N3—H11···O10.86 (1)1.99 (1)2.850 (3)178 (2)
N3—H12···O2i0.85 (1)2.05 (1)2.901 (2)178 (2)

Symmetry codes: (i) x, y−1, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU2705).

References

  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  • Czupiński, O., Wojtaś, M., Ciunik, Z. & Jakubas, R. (2005). Solid State Sci.8, 86–96.
  • Higashi, T. (1995). ABSCOR Rigaku Corporation, Tokyo, Japan.
  • Lee, J.-H. P., Lewis, B. D., Mendes, J. M., Turnbull, M. M. & Awwadi, F. F. (2003). J. Coord. Chem.56, 1425–1442.
  • Rigaku (1998). RAPID-AUTO Rigaku Corporation, Tokyo, Japan.
  • Rigaku/MSC (2002). CrystalClear Rigaku/MSC Inc., The Woodlands, Texas, USA.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Westrip, S. P. (2009). publCIF In preparation.
  • Ye, M.-D., Hu, M.-L. & Ye, C.-P. (2002). Z. Kristallogr. New Cryst. Struct.217, 501–502.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography