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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 [sigma](C-C) = 0.003 Å
R = 0.049
wR = 0.126
Data-to-parameter ratio = 17.7
Details
Open access

3-Methoxybenzohydrazide

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-H...N, N-H...O and C-H...O hydrogen bonds.

Related literature

For related structures, see: Ashiq, Jamal et al. (2008[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.], 2009a[Ashiq, U., Jamal, R. A., Tahir, M. N., Yousuf, S. & Khan, I. U. (2009a). Acta Cryst. E65, o1551.],b[Ashiq, U., Jamal, R. A., Arshad, M. N., Maqsood, Z. T. & Khan, I. U. (2009b). Acta Cryst. E65, o2360.]); Jamal et al. (2008[Jamal, R. A., Ashiq, U., Arshad, M. N., Maqsood, Z. T. & Khan, I. U. (2008). Acta Cryst. E64, o2188.], 2009[Jamal, R. A., Ashiq, U., Arshad, M. N., Maqsood, Z. T. & Khan, I. U. (2009). Acta Cryst. E65, o1764.]); Kallel et al. (1992[Kallel, A., Amor, B. H., Svoboda, I. & Fuess, H. (1992). Z. Kristallogr. 198, 137-140.]); Saraogi et al. (2002[Saraogi, I., Mruthyunjayaswamy, B. H. M., Ijare, O. B., Jadegoud, Y. & Guru Row, T. N. (2002). Acta Cryst. E58, o1341-o1342.]). For the biological activity of hydrazides, see: Ara et al. (2007[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, Ara et al. (2008[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.]).

[Scheme 1]

Experimental

Crystal data
  • C8H10N2O2

  • Mr = 166.18

  • Monoclinic, P 21 /n

  • a = 13.1288 (8) Å

  • b = 7.5417 (4) Å

  • c = 17.0734 (10) Å

  • [beta] = 92.857 (3)°

  • V = 1688.40 (17) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 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[Bruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.979, Tmax = 0.990

  • 18386 measured reflections

  • 4200 independent reflections

  • 1708 reflections with I > 2[sigma](I)

  • Rint = 0.066

Refinement
  • R[F2 > 2[sigma](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

  • [Delta][rho]max = 0.15 e Å-3

  • [Delta][rho]min = -0.22 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N11-H11N...N12i 0.91 (2) 2.12 (2) 2.958 (2) 153.3 (18)
N11-H11N...N11i 0.91 (2) 2.63 (2) 3.191 (2) 120.9 (13)
N12-H12N...O11ii 0.95 (2) 2.30 (2) 3.193 (2) 155.2 (18)
N12-H13N...N22iii 0.85 (2) 2.47 (2) 3.185 (3) 142.6 (19)
N21-H21N...O11iv 0.87 (2) 1.99 (2) 2.860 (2) 172 (2)
N22-H23N...O21v 0.88 (2) 2.14 (2) 3.007 (2) 168 (2)
C18-H18C...O21vi 0.96 2.58 3.498 (3) 160
C22-H22...O11iv 0.93 2.35 3.208 (3) 153
C26-H26...O21vii 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[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: ORTEP-3 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); 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.  [CrossRef] [PubMed] [ChemPort]
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.  [CrossRef] [PubMed] [ChemPort]
Ashiq, U., Jamal, R. A., Arshad, M. N., Maqsood, Z. T. & Khan, I. U. (2009b). Acta Cryst. E65, o2360.  [CSD] [CrossRef] [details]
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.  [CSD] [CrossRef]
Ashiq, U., Jamal, R. A., Tahir, M. N., Yousuf, S. & Khan, I. U. (2009a). Acta Cryst. E65, o1551.  [CSD] [CrossRef] [details]
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.  [CrossRef] [details]
Jamal, R. A., Ashiq, U., Arshad, M. N., Maqsood, Z. T. & Khan, I. U. (2008). Acta Cryst. E64, o2188.  [CSD] [CrossRef] [details]
Jamal, R. A., Ashiq, U., Arshad, M. N., Maqsood, Z. T. & Khan, I. U. (2009). Acta Cryst. E65, o1764.  [CSD] [CrossRef] [details]
Kallel, A., Amor, B. H., Svoboda, I. & Fuess, H. (1992). Z. Kristallogr. 198, 137-140.  [ChemPort]
Saraogi, I., Mruthyunjayaswamy, B. H. M., Ijare, O. B., Jadegoud, Y. & Guru Row, T. N. (2002). Acta Cryst. E58, o1341-o1342.  [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]


Acta Cryst (2009). E65, o2473  [ doi:10.1107/S1600536809036526 ]

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