3-Methyl­benzene-1,2-diamine

Yang, X.-L.; Feng, Z.-Q.; Hao, L.-Y.

doi:10.1107/S1600536812046120

Volume 68
Part 12
Page o3346
December 2012

Received 27 October 2012
Accepted 8 November 2012
Online 14 November 2012

Key indicators
Single-crystal X-ray study
T = 291 K
Mean (C-C) = 0.002 Å
R = 0.045
wR = 0.124
Data-to-parameter ratio = 11.8
Details

3-Methylbenzene-1,2-diamine

Xiao-Li Yang,^a ^* Zhi-Qiang Feng ^a and Ling-Yun Hao ^a

^aSchool of Material Engineering, Jinling Institute of Technology, Nanjing 211169, People's Republic of China
Correspondence e-mail: yangjianming7706@sina.com

The title compound, C₇H₁₀N₂, was synthesized from 2-methyl-6-nitroaniline by a reduction reaction. In the crystal, molecules are linked via N-HN hydrogen bonds, forming two-dimensional networks lying parallel to (100). These networks are stabilized by C-H [pi] and N-H [pi] interactions.

Related literature

The title compound is an important organic synthesis intermediate. For background to its applications, see: Wen et al. (2009). For the synthetic procedure, see: Li et al. (2011). For bond-length data, see: Allen et al. (1987).

Experimental

Crystal data

C₇H₁₀N₂
M_r = 122.17
Monoclinic, P 2₁ /c
a = 11.836 (2) Å
b = 7.7160 (15) Å
c = 7.7430 (15) Å
= 90.72 (3)°
V = 707.1 (2) Å³
Z = 4
Mo K radiation
= 0.07 mm^-1
T = 291 K
0.3 × 0.2 × 0.1 mm

Data collection

Enraf-Nonius CAD-4 diffractometer
Absorption correction: scan (North et al., 1968) T_min = 0.979, T_max = 0.993
2693 measured reflections
1300 independent reflections
962 reflections with I > 2(I)
R_int = 0.060
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F² > 2(F²)] = 0.045
wR(F²) = 0.124
S = 1.00
1300 reflections
110 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.13 e Å^-3
_min = -0.12 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of C1-C6 ring.

D-HA	D-H	HA	DA	D-HA
N1-H1AN2ⁱ	0.91 (2)	2.36 (2)	3.237 (2)	163.5 (16)
N2-H2AN1ⁱⁱ	0.84 (2)	2.48 (2)	3.248 (2)	152.2 (19)
C2-H2Cg1ⁱⁱⁱ	0.93	2.85	3.6713 (18)	148
N2-H2BCg1^iv	0.90 (2)	2.776 (18)	3.5192 (17)	141.2 (16)
Symmetry codes: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) -x+1, -y+1, -z+1; (iii) $[x, -y+{\script{1\over 2}}, z-{\script{3\over 2}}]$ ; (iv) $[x, -y-{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: CAD-4 Software (Enraf-Nonius, 1985); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo,1995); 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: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BQ2378 ).

Acknowledgements

This work was supported by the Doctoral Fund of Jinling Institute of Technology (jit-b-201227). The authors thank the Center of Test and Analysis, Nanjing University, for the data collection.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Enraf-Nonius (1985). CAD-4 Software. Enraf-Nonius, Delft, The Netherlands.
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.
Li, Y., Zhang, H. B., Liu, Y. Y., Li, F. S. & Liu, X. N. (2011). J. Mol. Struct. 997, 110-116.
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Wen, H. L., Yao, K. S., Zhang, Y. D., Zhou, Z. M. & Kirschning, A. (2009). Catal. Commun. 10, 1207-1211.

organic compounds