N-Methyl-4-nitro­anilinium chloride

Jian-Long Wang; Fu-Rong Zhou; Fei-Yun Wei

doi:10.1107/S1600536812024117

. 2012 May 31;68(Pt 6):o1973. doi: 10.1107/S1600536812024117

N-Methyl-4-nitroanilinium chloride

Jian-Long Wang ^a,^*, Fu-Rong Zhou ^a, Fei-Yun Wei ^a

PMCID: PMC3379520 PMID: 22719718

Abstract

The asymmetric unit of the title salt, C₇H₉N₂O₂ ⁺·Cl⁻, contains two independent cations and anions. In the crystal, each N-methyl-4-nitroanilinium cation is linked to two Cl⁻ anions via N—H⋯Cl hydrogen bonds. π–π stacking is observed between the benzene rings of adjacent cations [centroid-to-centroid distances = 3.7684 (14) and 3.7917 (7) Å].

Related literature

For applications of N-methyl-4-nitrobenzenamine, see: Bellamy & Sammour (1993 ▶); Sammour (1994 ▶); Williams & Friedlander (2000 ▶); Davies & Provatas (2006 ▶). graphic file with name e-68-o1973-scheme1.jpg

Experimental

Crystal data

C₇H₉N₂O₂ ⁺·Cl⁻
M _r = 188.61
Monoclinic,
a = 7.0509 (14) Å
b = 19.120 (4) Å
c = 13.443 (3) Å
β = 95.20 (3)°
V = 1804.8 (6) Å³
Z = 8
Mo Kα radiation
μ = 0.39 mm⁻¹
T = 293 K
0.20 × 0.20 × 0.12 mm

Data collection

Rigaku Saturn diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T _min = 0.927, T _max = 0.955
17869 measured reflections
4282 independent reflections
3022 reflections with I > 2σ(I)
R _int = 0.051

Refinement

R[F ² > 2σ(F ²)] = 0.046
wR(F ²) = 0.124
S = 1.03
4282 reflections
236 parameters
4 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Data collection: RAPID-AUTO (Rigaku, 2000 ▶); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2000 ▶); program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812024117/xu5532sup1.cif

e-68-o1973-sup1.cif^{(18.9KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812024117/xu5532Isup2.hkl

e-68-o1973-Isup2.hkl^{(209.8KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812024117/xu5532Isup3.cml

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⋯Cl2ⁱ	0.90 (1)	2.18 (1)	3.0702 (17)	170 (2)
N2—H2B⋯Cl1ⁱ	0.89 (1)	2.16 (1)	3.0482 (19)	173 (2)
N4—H4A⋯Cl2ⁱⁱ	0.90 (1)	2.15 (1)	3.0361 (18)	168 (2)
N4—H4B⋯Cl1	0.89 (1)	2.26 (1)	3.1157 (18)	163 (2)

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

Acknowledgments

The authors thank China North Industries Group Corporation for financial support.

supplementary crystallographic information

Comment

As a stablizer, N-methyl-4-nitrobenzenamine is used in order to lengthen the useful service life of double-base and minimum smoke propellants (Bellamy & Sammour, 1993; Sammour, 1994; Williams & Friedlander, 2000). As a important ingredient, N-methyl-4-nitrobenzenamine can improve melt-cast explosive systems mechanical properties (Davies & Provatas, 2006). In order to research reaction properties, here we report the synthesis and the crystal structure of the title compound (Fig. 1).

The title compound consists of a N-(4-nitrophenyl)-methylammonium cation and a chloride anion. The hydrochloric acid deprotonated and the N-methyl-4-nitrobenzenamine accepts the proton to produce the protonated organic cation, namely N-(4-nitrophenyl)-methylammonium chloride. In the crystal structure, contains two cations and two anions. They are linked by N—H···Cl hydrogen bonds to form a three-dimensional complex network.

Experimental

The title compound was synthesized by N-methyl-4-nitrobenzenamine and concentrated hydrochloric acid in acetone at room temperature. Single crystals suitable for X-ray diffraction were obtained by evaporation of a solution of the title compound in acetone at room temperature.