3-Methoxy­benzohydrazide

Jamal, R.A.; Ashiq, U.; Arshad, M.N.; Maqsood, Z.T.; Khan, I.U.

doi:10.1107/S1600536809036526

Volume 65
Part 10
Page o2473
October 2009

Received 6 September 2009
Accepted 9 September 2009
Online 16 September 2009

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.003 Å
R = 0.049
wR = 0.126
Data-to-parameter ratio = 17.7
Details

3-Methoxybenzohydrazide

Rifat Ara Jamal,^a ^* Uzma Ashiq,^a Muhammad Nadeem Arshad,^b Zahida Tasneem Maqsood ^a and Islam Ullah Khan ^b

^aDepartment of Chemistry, University of Karachi, Karachi 75270, Pakistan, and ^bDepartment of Chemistry, Government College University, Lahore, Pakistan
Correspondence e-mail: rifat_jamal@yahoo.com

The title compound, C₈H₁₀N₂O₂, crystallizes with two independent molecules in an asymmetric unit. The structure is stabilized by nine intermolecular N-HN, N-HO and C-HO hydrogen bonds.

Related literature

For related structures, see: Ashiq, Jamal et al. (2008, 2009a,b); Jamal et al. (2008, 2009); Kallel et al. (1992); Saraogi et al. (2002). For the biological activity of hydrazides, see: Ara et al. (2007); Ashiq, Ara et al. (2008).

Experimental

Crystal data

C₈H₁₀N₂O₂
M_r = 166.18
Monoclinic, P 2₁ /n
a = 13.1288 (8) Å
b = 7.5417 (4) Å
c = 17.0734 (10) Å
= 92.857 (3)°
V = 1688.40 (17) Å³
Z = 8
Mo K radiation
= 0.10 mm^-1
T = 296 K
0.39 × 0.15 × 0.11 mm

Data collection

Bruker KAPPA APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005) T_min = 0.979, T_max = 0.990
18386 measured reflections
4200 independent reflections
1708 reflections with I > 2(I)
R_int = 0.066

Refinement

R[F² > 2(F²)] = 0.049
wR(F²) = 0.126
S = 0.95
4200 reflections
237 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.15 e Å^-3
_min = -0.22 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N11-H11NN12ⁱ	0.91 (2)	2.12 (2)	2.958 (2)	153.3 (18)
N11-H11NN11ⁱ	0.91 (2)	2.63 (2)	3.191 (2)	120.9 (13)
N12-H12NO11ⁱⁱ	0.95 (2)	2.30 (2)	3.193 (2)	155.2 (18)
N12-H13NN22ⁱⁱⁱ	0.85 (2)	2.47 (2)	3.185 (3)	142.6 (19)
N21-H21NO11^iv	0.87 (2)	1.99 (2)	2.860 (2)	172 (2)
N22-H23NO21^v	0.88 (2)	2.14 (2)	3.007 (2)	168 (2)
C18-H18CO21^vi	0.96	2.58	3.498 (3)	160
C22-H22O11^iv	0.93	2.35	3.208 (3)	153
C26-H26O21^vii	0.93	2.56	3.439 (3)	157
Symmetry codes: (i) -x+1, -y+1, -z+2; (ii) -x+1, -y, -z+2; (iii) x, y-1, z+1; (iv) x, y+1, z-1; (v) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (vi) -x+1, -y+1, -z+1; (vii) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); 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 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: PV2207 ).

Acknowledgements

The authors thank the Higher Education Commission, Pakistan, for providing the diffractometer at GCU, Lahore, and Bana International for their support in collecting the crystallographic data.

References

Ara, R., Ashiq, U., Mahroof-Tahir, M., Maqsood, Z. T., Khan, K. M., Lodhi, M. A. & Choudhary, M. I. (2007). Chem. Biodivers. 4, 58-71.
Ashiq, U., Ara, R., Mahroof-Tahir, M., Maqsood, Z. T., Khan, K. M., Khan, S. N., Siddiqui, H. & Choudhary, M. I. (2008). Chem. Biodivers. 5, 82-92.
Ashiq, U., Jamal, R. A., Arshad, M. N., Maqsood, Z. T. & Khan, I. U. (2009b). Acta Cryst. E65, o2360.
Ashiq, U., Jamal, R. A., Mahroof-Tahir, M., Keramidas, A. D., Maqsood, Z. T., Khan, K. M. & Tahir, M. N. (2008). Anal. Sci. X. 24, 103-104.
Ashiq, U., Jamal, R. A., Tahir, M. N., Yousuf, S. & Khan, I. U. (2009a). Acta Cryst. E65, o1551.
Bruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Jamal, R. A., Ashiq, U., Arshad, M. N., Maqsood, Z. T. & Khan, I. U. (2008). Acta Cryst. E64, o2188.
Jamal, R. A., Ashiq, U., Arshad, M. N., Maqsood, Z. T. & Khan, I. U. (2009). Acta Cryst. E65, o1764.
Kallel, A., Amor, B. H., Svoboda, I. & Fuess, H. (1992). Z. Kristallogr. 198, 137-140.
Saraogi, I., Mruthyunjayaswamy, B. H. M., Ijare, O. B., Jadegoud, Y. & Guru Row, T. N. (2002). Acta Cryst. E58, o1341-o1342.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds