4-Iodo­anilinium nitrate

Xue-qun Fu

doi:10.1107/S1600536810016740

. 2010 May 12;66(Pt 6):o1326. doi: 10.1107/S1600536810016740

4-Iodoanilinium nitrate

Xue-qun Fu ^a,^*

PMCID: PMC2979466 PMID: 21579417

Abstract

In the title compound, C₆H₇IN⁺·NO₃ ⁻, π–π stacking interactions [centroid–centroid distances = 4.014 (4) and 4.029 (4) Å] stabilize the crystal structure and strong N—H⋯O and N—H⋯N hydrogen bonds link the cations and anions into zigzag chains running parallel to the c axis. The asymmetric unit contains two unique cations and anions

Related literature

For background to phase-transition materials, see: Li et al. (2008 ▶); Zhang et al. (2009 ▶).

Experimental

Crystal data

C₆H₇IN⁺·NO₃ ⁻
M _r = 282.04
Monoclinic,
a = 21.847 (4) Å
b = 5.6103 (11) Å
c = 15.928 (3) Å
β = 110.11 (3)°
V = 1833.2 (6) Å³
Z = 8
Mo Kα radiation
μ = 3.47 mm⁻¹
T = 298 K
0.40 × 0.30 × 0.20 mm

Data collection

Rigaku SCXmini diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T _min = 0.5, T _max = 0.5
17732 measured reflections
4196 independent reflections
3075 reflections with I > 2σ(I)
R _int = 0.041

Refinement

R[F ² > 2σ(F ²)] = 0.056
wR(F ²) = 0.112
S = 1.13
4196 reflections
217 parameters
H-atom parameters constrained
Δρ_max = 1.07 e Å⁻³
Δρ_min = −0.78 e Å⁻³

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; 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: PRPKAPPA (Ferguson, 1999 ▶).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810016740/jh2153sup1.cif

e-66-o1326-sup1.cif^{(16.5KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810016740/jh2153Isup2.hkl

e-66-o1326-Isup2.hkl^{(205.7KB, 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
N1—H1B⋯O4ⁱ	0.89	2.18	2.945 (8)	144
N1—H1C⋯O2ⁱⁱ	0.89	2.24	2.819 (8)	122
N1—H1C⋯O5ⁱ	0.89	2.46	3.010 (8)	120
N1—H1D⋯O3ⁱ	0.89	2.46	2.898 (8)	111
N1—H1D⋯I1ⁱⁱ	0.89	3.15	3.990 (6)	157
N2—H2B⋯O6ⁱⁱⁱ	0.89	2.03	2.892 (8)	162
N2—H2B⋯O4ⁱⁱⁱ	0.89	2.44	3.104 (8)	132
N2—H2B⋯N4ⁱⁱⁱ	0.89	2.55	3.372 (8)	153
N2—H2C⋯O3^iv	0.89	1.91	2.795 (7)	173
N2—H2C⋯N3^iv	0.89	2.56	3.407 (8)	159
N2—H2C⋯O1^iv	0.89	2.59	3.264 (8)	133
N2—H2D⋯O5^v	0.89	2.18	3.018 (8)	157
N2—H2D⋯O6^v	0.89	2.28	3.053 (8)	145
N2—H2D⋯N4^v	0.89	2.58	3.459 (9)	170

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

Acknowledgments

The author is grateful to the starter fund of Southeast University for financial support to buy the X-ray diffractometer.

supplementary crystallographic information

Comment

As a continuation of our study of phase transition materials, including organic ligands (Li et al., 2008), metal-organic coordination compounds (Zhang et al., 2009 ), organic-inorganic hybrids, we studied the dielectric properties of the title compound, unfortunately, there was no distinct anomaly observed from 93 K to 380 K, (m.p. 408 K-410 K). In this article, the crystal structure of (I) has been presented.

The asymmetric unit of the title compound is built up from two 4-iodobenzenammnium cations wherein the dihedral angle between plans formed by non-hydrogen atoms is 15.3 (2)°,and two nitrate radical anions (Fig.1). The π-π packing interaction of adjacent benzene rings with Cg(1)—Cg(1), 4.029 (4)Å; Cg(2)—Cg(2), 4.014 (4)Å [Cg(1) and Cg(2) are the centroids of benzene rings, where Cg(1): C(1) to C(6); Cg(2): C(7) to C(12)], make great contribution to the stability of the crystal structure. The strong intermolecular N—H···O (N···O distances 2.795 (7)-3.264 (8)Å) and N—H···N (N···N distances 3.372 (8)-3.459 (9)Å) hydrogen bonding link cations and anions into zigzag chains along c axis.

Experimental

Single crystals of 4-iodoanilinium nitrate were prepared by slow evaporation at room temperature of an ethanol solution of equal molar 4-iodobenzenamine and nitrate acid.