9-Amino­acridinium nitrate monohydrate

Mehrdad Pourayoubi; Hossein Eshtiagh-Hosseini; Somayyeh Sanaei Ataabadi; Teresa Mancilla Percino; Marco A Leyva Ramírez

doi:10.1107/S1600536811003953

. 2011 Feb 5;67(Pt 3):o565. doi: 10.1107/S1600536811003953

9-Aminoacridinium nitrate monohydrate

Mehrdad Pourayoubi ^a,^*, Hossein Eshtiagh-Hosseini ^a, Somayyeh Sanaei Ataabadi ^b, Teresa Mancilla Percino ^c, Marco A Leyva Ramírez ^c

PMCID: PMC3052121 PMID: 21522328

Abstract

The pyridine N atom of the cation in the title hydrated salt, C₁₃H₁₁N₂ ⁺·NO₃ ⁻·H₂O, is protonated; the N atom of the NH₂ group shows a planar conformation. The former N atom is hydrogen bonded to a water molecule. The amino group is involved in three N—H⋯O hydrogen bonds with two neighboring nitrate anions. The water molecule is hydrogen bonded to two adjacent nitrate anions. In the crystal, this results in a layered network.

Related literature

For the structure of 9-aminoacridine hydrochloride monohydrate, see: Talacki et al. (1974 ▶). For positive-charge-assisted hydrogen bonds, see: Gilli et al. (1994 ▶).

Experimental

Crystal data

C₁₃H₁₁N₂ ⁺·NO₃ ⁻·H₂O
M _r = 275.26
Triclinic,
a = 6.8556 (2) Å
b = 10.0532 (2) Å
c = 10.5912 (3) Å
α = 117.016 (1)°
β = 94.138 (1)°
γ = 97.995 (1)°
V = 636.36 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 293 K
0.75 × 0.75 × 0.45 mm

Data collection

Nonius KappaCCD diffractometer
Absorption correction: multi-scan (Blessing, 1995 ▶) T _min = 0.923, T _max = 0.953
8945 measured reflections
2822 independent reflections
2054 reflections with I > 2σ(I)
R _int = 0.028

Refinement

R[F ² > 2σ(F ²)] = 0.045
wR(F ²) = 0.132
S = 1.04
2822 reflections
201 parameters
5 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Data collection: COLLECT (Nonius, 2001 ▶); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO (Otwinowski & Minor, 1997 ▶) and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and enCIFer (Allen et al., 2004 ▶).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811003953/ng5102sup1.cif

e-67-0o565-sup1.cif^{(18KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811003953/ng5102Isup2.hkl

e-67-0o565-Isup2.hkl^{(135.7KB, hkl)}

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O1ⁱ	0.93 (1)	2.23 (2)	3.0619 (17)	149 (1)
N2—H2A⋯O3ⁱ	0.93 (1)	2.30 (2)	3.0662 (16)	140 (1)
N2—H2B⋯O2ⁱⁱ	0.90 (1)	2.07 (1)	2.9123 (15)	157 (2)
O4—H4A⋯O3ⁱⁱⁱ	0.91 (2)	2.03 (2)	2.9147 (18)	164 (2)
N1—H1⋯O4	0.89 (1)	1.91 (1)	2.7867 (15)	170 (2)
O4—H4B⋯O1	0.90 (2)	2.01 (2)	2.9058 (18)	173 (2)
O4—H4B⋯O2	0.90 (2)	2.64 (2)	3.2039 (19)	122 (2)

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

Acknowledgments

Support of this investigation by Ferdowsi University of Mashhad and the Islamic Azad University Shahr-e-Rey Branch is gratefully acknowledged.

supplementary crystallographic information

Comment

In a previous work, the crystal structure of 9-aminoacridine hydrochloride monohydrate (Talacki et al., 1974) has been investigated. Here, we report on the crystal structure of title hydrated salt, C₁₃H₁₁N₂⁺.NO₃^-.H₂O (Fig. 1).

In 9-amino-acridinium cation, the heteroatom N1 and the nitrogen atom of NH₂ unit (N2) have a sp² character. The C1—N1—C13 angle is 122.68 (11)°; the fused tricyclic system is essentially planar.

The protonated pyridine nitrogen atom is involving in a positive charge assisted (Gilli et al., 1994) N—H···O hydrogen bond with a neighboring H₂O molecule (N1···O4 = 2.7867 (15) Å). Moreover, the water molecule forms two O—H···O hydrogen bonds (O···O = 2.9058 (18) & 2.9147 (18) Å) with two adjacent NO₃^- anions; also, the weak hydrogen bond O4—H4B···O2 (O4···O2 = 3.2039 (19) Å) may be considered which has not influence on the pattern of crystal packing. The NH₂ unit of cation cooperates in three N—H···O hydrogen bonds (N···O = 2.9123 (15), 3.0619 (17) and 3.0662 (16) Å), with two neighboring nitrate anions. Cations, anions and water molecules are hydrogen bonded in a 2-D arrangement (Fig. 2).

Experimental

The title hydrated salt was obtained fortuitously from the reaction between 9-aminoacridine and Fe(NO₃)₃.9H₂O in CH₃OH as follows: To a solution of 9-aminoacridine (0.194 g, 1 mmol) in CH₃OH (5 ml), a solution of Fe(NO₃)₃.9H₂O (0.202 g, 0.5 mmol) in CH₃OH (5 ml) was added at 343 K. After 1 h stirring, the solid was filtered; the crystals were obtained from methanolic solution after a slow evaporation at room temperature.