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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 [sigma](C-C) = 0.002 Å
R = 0.045
wR = 0.124
Data-to-parameter ratio = 11.8
Details
Open access

3-Methylbenzene-1,2-diamine

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-H...N 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[Wen, H. L., Yao, K. S., Zhang, Y. D., Zhou, Z. M. & Kirschning, A. (2009). Catal. Commun. 10, 1207-1211.]). For the synthetic procedure, see: Li et al. (2011[Li, Y., Zhang, H. B., Liu, Y. Y., Li, F. S. & Liu, X. N. (2011). J. Mol. Struct. 997, 110-116.]). For bond-length data, see: Allen et al. (1987[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.]).

[Scheme 1]

Experimental

Crystal data
  • C7H10N2

  • Mr = 122.17

  • Monoclinic, P 21 /c

  • a = 11.836 (2) Å

  • b = 7.7160 (15) Å

  • c = 7.7430 (15) Å

  • [beta] = 90.72 (3)°

  • V = 707.1 (2) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.07 mm-1

  • T = 291 K

  • 0.3 × 0.2 × 0.1 mm

Data collection
  • Enraf-Nonius CAD-4 diffractometer

  • Absorption correction: [psi] scan (North et al., 1968[North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.]) Tmin = 0.979, Tmax = 0.993

  • 2693 measured reflections

  • 1300 independent reflections

  • 962 reflections with I > 2[sigma](I)

  • Rint = 0.060

  • 3 standard reflections every 200 reflections intensity decay: 1%

Refinement
  • R[F2 > 2[sigma](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

  • [Delta][rho]max = 0.13 e Å-3

  • [Delta][rho]min = -0.12 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of C1-C6 ring.

D-H...A D-H H...A D...A D-H...A
N1-H1A...N2i 0.91 (2) 2.36 (2) 3.237 (2) 163.5 (16)
N2-H2A...N1ii 0.84 (2) 2.48 (2) 3.248 (2) 152.2 (19)
C2-H2...Cg1iii 0.93 2.85 3.6713 (18) 148
N2-H2B...Cg1iv 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[Enraf-Nonius (1985). CAD-4 Software. Enraf-Nonius, Delft, The Netherlands.]); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo,1995[Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); 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.  [ISI] [CSD] [CrossRef] [ChemPort]
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.  [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Wen, H. L., Yao, K. S., Zhang, Y. D., Zhou, Z. M. & Kirschning, A. (2009). Catal. Commun. 10, 1207-1211.  [ISI] [CrossRef] [ChemPort]


Acta Cryst (2012). E68, o3346  [ doi:10.1107/S1600536812046120 ]

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