3-Methyl-4-nitro­phenol–4-dimethyl­amino­pyridine (1/1)

Muralidharan, S.; Nagapandiselvi, P.; Srinivasan, T.; Gopalakrishnan, R.; Velmurugan, D.

doi:10.1107/S1600536812041670

Volume 68
Part 11
Page o3106
November 2012

Received 20 September 2012
Accepted 5 October 2012
Online 13 October 2012

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.002 Å
R = 0.056
wR = 0.185
Data-to-parameter ratio = 19.0
Details

3-Methyl-4-nitrophenol-4-dimethylaminopyridine (1/1)

Srinivasan Muralidharan,^a Perumal Nagapandiselvi,^a Thothadri Srinivasan,^b Rengasamy Gopalakrishnan ^a and Devadasan Velmurugan ^b ^*

^aDepartment of Physics, Anna University, Chennai 600 025, India, and ^bCentre of Advanced Study in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai 600 025, India
Correspondence e-mail: shirai2011@gmail.com

In the title adduct, C₇H₇NO₃^.C₇H₁₀N₂, the dihedral angle betwen the benzene ring and pyridine rings is 9.60 (8)° while the nitro group attached to the benzene ring makes a dihedral angle of 21.76 (13)°. The hydroxyl O atom deviates by 0.0247 (15) Å from the plane of the benzene ring. The crystal packing features O-HN hydrogen bonds.

Related literature

For a related structure, see: Dong & Cheng (2012).

Experimental

Crystal data

C₇H₇NO₃·C₇H₁₀N₂
M_r = 275.31
Monoclinic, P 2₁ /c
a = 11.4923 (9) Å
b = 9.8362 (8) Å
c = 12.7781 (10) Å
= 103.870 (5)°
V = 1402.3 (2) Å³
Z = 4
Mo K radiation
= 0.09 mm^-1
T = 293 K
0.35 × 0.30 × 0.30 mm

Data collection

Bruker SMART APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008) T_min = 0.968, T_max = 0.973
13307 measured reflections
3498 independent reflections
2469 reflections with I > 2(I)
R_int = 0.028

Refinement

R[F² > 2(F²)] = 0.056
wR(F²) = 0.185
S = 1.03
3498 reflections
184 parameters
H-atom parameters constrained
_max = 0.35 e Å^-3
_min = -0.27 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O3-H3N3ⁱ	0.82	1.79	2.594 (2)	168
Symmetry code: (i) $[-x, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: PV2590 ).

Acknowledgements

The authors thank the TBI X-ray facility, CAS in Crystallography and Biophysics, University of Madras, India, for the data collection. TS thanks the DST for an Inspire fellowship.

References

Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, U. S. A.
Dong, S.-L. & Cheng, X. (2012). Acta Cryst. E68, o518.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds