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Volume 69 
Part 8 
Pages o1203-o1204  
August 2013  

Received 1 July 2013
Accepted 2 July 2013
Online 6 July 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.003 Å
R = 0.055
wR = 0.144
Data-to-parameter ratio = 17.1
Details
Open access

1-(2,4-Dinitrophenyl)-2-[(E)-2,4,5-trimethoxybenzylidene]hydrazine

aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia,bDepartment of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand, and cFaculty of Traditional Thai Medicine, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand
Correspondence e-mail: hkfun@usm.my

The title compound, C16H16N4O7, is close to being planar, with a dihedral angle of 3.15 (11)° between the benzene rings. The methoxy groups at the ortho- and para-positions of the 2,4,5-trimethoxyphenyl group are almost coplanar with the ring [deviations of the C atoms = 0.017 (2) and -0.025 (2) Å, respectively], whereas the meta-methoxy group deviates slightly [C-atom displacement = 0.162 (2) Å]. Both the ortho- and para-nitro groups are close to being coplanar with their attached ring [dihedral angles = 7.81 (12) and 8.56 (11)°, respectively]. An intramolecular N-H...O hydrogen bond generates an S(6) ring motif. In the crystal, inversion dimers linked by pairs of N-H...O hydrogen bonds involving the same H atom as the intramolecular bond generate R22(12) loops. The dimers are linked by weak C-H...O interactions into sheets parallel to the (10-4) plane and the sheets are stacked by [pi]-[pi] interactions, with a centroid-centroid distance of 3.5974 (14) Å.

Related literature

For related structures, see: Fun et al. (2011[Fun, H.-K., Nilwanna, B., Jansrisewangwong, P., Kobkeatthawin, T. & Chantrapromma, S. (2011). Acta Cryst. E67, o3202-o3203.], 2012[Fun, H.-K., Chantrapromma, S., Nilwanna, B. & Kobkeatthawin, T. (2012). Acta Cryst. E68, o2144-o2145.]). For background to the biological activity of hydrozones, see: Angelusiu et al. (2010[Angelusiu, M.-V., Barbuceanu, S.-F., Draghici, C. & Almajan, G.-L. (2010). Eur. J. Med. Chem. 45, 2055-2062.]); Cui et al. (2010[Cui, Z., Li, Y., Ling, Y., Huang, J., Cui, J., Wang, R. & Yang, X. (2010). Eur. J. Med. Chem. 45, 5576-5584.]); Gokce et al. (2009[Gokce, M., Utku, S. & Kupeli, E. (2009). Eur. J. Med. Chem. 44, 3760-3764.]); Molyneux (2004[Molyneux, P. (2004). Songklanakarin J. Sci. Technol. 26, 211-219.]); Török et al. (2013[Török, B., Sood, A., Bag, S., Tulsan, R., Ghosh, S., Borkin, D., Kennedy, A. R., Melanson, M., Madden, R., Zhou, W., LeVine, H. & Török, M. (2013). Biochemistry, 52, 1137-1148.]); Wang et al. (2009[Wang, Q., Yang, Z. Y., Qi, G.-F. & Qin, D.-D. (2009). Eur. J. Med. Chem. 44, 2425-2433.]).

[Scheme 1]

Experimental

Crystal data
  • C16H16N4O7

  • Mr = 376.33

  • Monoclinic, P 21 /c

  • a = 8.0273 (13) Å

  • b = 15.048 (2) Å

  • c = 13.686 (2) Å

  • [beta] = 101.546 (3)°

  • V = 1619.7 (4) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.12 mm-1

  • T = 100 K

  • 0.33 × 0.06 × 0.05 mm

Data collection
  • Bruker SMART APEXII DUO CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.961, Tmax = 0.994

  • 14507 measured reflections

  • 4296 independent reflections

  • 2385 reflections with I > 2[sigma](I)

  • Rint = 0.072

Refinement
  • R[F2 > 2[sigma](F2)] = 0.055

  • wR(F2) = 0.144

  • S = 1.01

  • 4296 reflections

  • 251 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.31 e Å-3

  • [Delta][rho]min = -0.33 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1N1...O1 0.89 (3) 2.04 (3) 2.642 (3) 124 (3)
N1-H1N1...O1i 0.89 (3) 2.43 (3) 3.295 (3) 164 (3)
C14-H14A...O6ii 0.96 2.59 3.180 (3) 120
C16-H16C...O2iii 0.96 2.53 3.143 (3) 122
Symmetry codes: (i) -x+2, -y+1, -z+1; (ii) [-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (iii) [x-1, -y+{\script{1\over 2}}, z-{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]) and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB7102 ).


Acknowledgements

The authors thank the Prince of Songkla University for generous support. The authors extend their appreciation to Universiti Sains Malaysia for the APEX DE2012 grant No.1002/PFIZIK/910323.

References

Angelusiu, M.-V., Barbuceanu, S.-F., Draghici, C. & Almajan, G.-L. (2010). Eur. J. Med. Chem. 45, 2055-2062.  [Web of Science] [CrossRef] [ChemPort] [PubMed]
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Cui, Z., Li, Y., Ling, Y., Huang, J., Cui, J., Wang, R. & Yang, X. (2010). Eur. J. Med. Chem. 45, 5576-5584.  [Web of Science] [CSD] [CrossRef] [ChemPort] [PubMed]
Fun, H.-K., Chantrapromma, S., Nilwanna, B. & Kobkeatthawin, T. (2012). Acta Cryst. E68, o2144-o2145.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Fun, H.-K., Nilwanna, B., Jansrisewangwong, P., Kobkeatthawin, T. & Chantrapromma, S. (2011). Acta Cryst. E67, o3202-o3203.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Gokce, M., Utku, S. & Kupeli, E. (2009). Eur. J. Med. Chem. 44, 3760-3764.  [Web of Science] [CrossRef] [PubMed]
Molyneux, P. (2004). Songklanakarin J. Sci. Technol. 26, 211-219.  [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Török, B., Sood, A., Bag, S., Tulsan, R., Ghosh, S., Borkin, D., Kennedy, A. R., Melanson, M., Madden, R., Zhou, W., LeVine, H. & Török, M. (2013). Biochemistry, 52, 1137-1148.  [Web of Science] [PubMed]
Wang, Q., Yang, Z. Y., Qi, G.-F. & Qin, D.-D. (2009). Eur. J. Med. Chem. 44, 2425-2433.  [Web of Science] [CSD] [CrossRef] [PubMed] [ChemPort]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1203-o1204   [ doi:10.1107/S1600536813018345 ]

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