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Volume 69 
Part 4 
Pages o491-o492  
April 2013  

Received 20 February 2013
Accepted 28 February 2013
Online 6 March 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.004 Å
R = 0.056
wR = 0.164
Data-to-parameter ratio = 13.8
Details
Open access

2-Amino-6-methyl-5-{5-[(naphthalen-2-yloxy)methyl]-1,3,4-oxadiazol-2-ylsulfanyl}-4-(3-nitrophenyl)pyridine-3-carbonitrile

aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia,bDepartment of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, PO Box 2457, Riyadh 11451, Saudi Arabia, and cDepartment of studies in Chemistry, Mangalore University, Mangalagangothri 574 199, India
Correspondence e-mail: hkfun@usm.my

The asymmetric unit of the title compound, C26H18N6O4S, contains two independent molecules (A and B). The dihedral angles between the oxadiazole ring and naphthalene ring system are 42.59 (14) and 6.88 (14) Å in molecules A and B, respectively. The dihedral angles between the pyridine and benzene rings in A and B are 65.53 (13 )and 87.67 (13) Å, respectively. In the crystal, molecules A and B are linked through a pair of N-H...N hydrogen bonds involving one -NH2 group H atom and second pair of N-H...N hydrogen bonds involving the other -NH2 group H atom, forming an -ABAB- ribbon along [100] containing R22(8) and R22(12) ring motifs. These ribbons are further connected by weak C-H...N, C-H...O and C-H...[pi] interactions, resulting in a three-dimensional network. The crystal studied was a non-merohedral twin with refined components 0.906 (1):0.094 (1).

Related literature

For background to pyridine chemistry, see: Youngdale (1980[Youngdale, G. A. (1980). US Patent 4 288 440.], 1982[Youngdale, G. A. (1982). Chem. Abstr. 96, 6596.]); Todd (1970a[Todd, A. H. (1970a). UK Patent 1 203 149.],b[Todd, A. H. (1970b). Chem. Abstr. 73, 120509.]); Lohaus et al. (1968[Lohaus, G., Dittmar, W. & Afric, S. (1968). Pat. 6 906, 036.], 1970[Lohaus, G., Dittmar, W. & Afric, S. (1970). Chem. Abstr. 73, 120508.]); Gachet et al. (1995[Gachet, C., Cattanea, M., Ohlmann, P., Lecchi, B., Cassel, J., Mannucci, P. & Cazenave, J. P. (1995). Br. J. Haematol. 91, 434.]); Yao et al. (1994[Yao, S. K., Ober, J. C., Ferguson, J. J., Maffrand, J. P., Anderson, H. V., Buja, L. M. & Willerson, J. T. (1994). Am. J. Physiol. pp. H488-H493.]); Umemura et al. (1995[Umemura, K., Kawai, H., Ishihara, H. & Nakashima, M. (1995). Jpn J. Pharmacol. 76, 253-258.]). For background to 1,3,4-oxadiazole chemistry, see: Jin et al. (2006[Jin, L., Chen, J., Song, B., Chen, Z., Yang, S., Li, Q., Hu, D. & Xu, R. (2006). Bioorg. Med. Chem. Lett. 16, 5036-5040.]); Bhandari et al. (2008[Bhandari, S. V., Bothara, K. G., Raut, M. K., Patil, A. A., Sarkate, A. P. & Mokale, V. J. (2008). Bioorg. Med. Chem. 16, 1822-1831.]); Krasovskii et al. (2000[Krasovskii, A. N., Bulgakov, A. K., Andrushko, A. P., Krasovskii, I. A., Dyachenko, A. M., Bokun, A. A., Kravchenko, N. A. & Demchenko, A. M. (2000). Pharm. Chem. J. 34, 115-117.]); Mishra et al. (1995[Mishra, L., Said, M. K., Itokawa, H. & Takeya, K. (1995). Bioorg. Med. Chem. Lett. 3, 1241-1245.]); Suman et al. (1979[Suman, S. P. & Bahel, S. C. V. (1979). J. Indian Chem. Soc. 56, 712.]). For hydrogen-bond motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]). For standard 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.]). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986[Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.]).

[Scheme 1]

Experimental

Crystal data
  • C26H18N6O4S

  • Mr = 510.52

  • Triclinic, [P \overline 1]

  • a = 9.6132 (9) Å

  • b = 9.8928 (10) Å

  • c = 25.724 (2) Å

  • [alpha] = 83.215 (2)°

  • [beta] = 84.102 (2)°

  • [gamma] = 72.564 (2)°

  • V = 2311.8 (4) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.19 mm-1

  • T = 100 K

  • 0.23 × 0.19 × 0.09 mm

Data collection
  • Bruker SMART APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.958, Tmax = 0.983

  • 9469 measured reflections

  • 9469 independent reflections

  • 8293 reflections with I > 2[sigma](I)

  • Rint = 0.000

Refinement
  • R[F2 > 2[sigma](F2)] = 0.056

  • wR(F2) = 0.164

  • S = 1.20

  • 9469 reflections

  • 686 parameters

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

  • [Delta][rho]max = 0.32 e Å-3

  • [Delta][rho]min = -0.36 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1, Cg2, Cg3 and Cg4 are the centroids of the C1B/C2B/C7B-C10B, C2B-C7B, C1A/C2A/C3A/C8A-C10A and O2A/C12A/N1A/N2A/C13A rings, respecively.

D-H...A D-H H...A D...A D-H...A
N4A-H2NA...N5Bi 0.86 (4) 2.21 (4) 3.025 (4) 158 (3)
N4A-H1NA...N3Bii 0.84 (4) 2.23 (4) 3.056 (4) 165 (4)
N4B-H2NB...N3Aii 0.92 (4) 2.08 (4) 2.991 (4) 174 (4)
N4B-H1NB...N5Ai 0.85 (5) 2.34 (5) 3.157 (4) 162 (4)
C11A-H11B...O1Biii 0.99 2.36 3.332 (4) 168
C11B-H11C...O3Biv 0.99 2.60 3.173 (4) 117
C21B-H21B...N2Av 0.95 2.54 3.333 (4) 142
C22A-H22A...N1Bvi 0.95 2.60 3.540 (4) 169
C2A-H2AA...Cg1vi 0.95 2.78 3.492 (3) 133
C4A-H4AA...Cg2vi 0.95 2.62 3.457 (4) 147
C7A-H7AA...Cg1iii 0.95 2.80 3.557 (3) 138
C3B-H3BA...Cg3vii 0.95 2.67 3.440 (3) 138
C8B-H8BA...Cg3viii 0.95 2.83 3.599 (3) 139
C24A-H24A...Cg4 0.95 2.92 3.652 (3) 135
Symmetry codes: (i) -x+1, -y+2, -z; (ii) -x, -y+2, -z; (iii) x, y-1, z; (iv) x-1, y, z; (v) x+1, y, z; (vi) x+1, y-1, z; (vii) -x, -y+1, -z+1; (viii) -x, -y+2, -z+1.

Data collection: APEX2 (Bruker, 2009[Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). SADABS, APEX2 and SAINT. 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 and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH5588 ).


Acknowledgements

The authors thank Universiti Sains Malaysia (USM) for the RUC grant (Structure Determination of 50 kDa Outer Membrane Proteins From S.typhi By X-ray Protein Crystallography, No. 1001/PSKBP/8630013) and APEX DE2012 grant (No. 1002/PFIZIK/910323). CSC thanks Universiti Sains Malaysia for a postdoctoral research fellowship. PP thanks the UGC, New Delhi, for the award of a junior research fellowship.

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.
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Bhandari, S. V., Bothara, K. G., Raut, M. K., Patil, A. A., Sarkate, A. P. & Mokale, V. J. (2008). Bioorg. Med. Chem. 16, 1822-1831.  [CrossRef] [PubMed] [ChemPort]
Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.  [CrossRef] [ChemPort] [ISI] [details]
Gachet, C., Cattanea, M., Ohlmann, P., Lecchi, B., Cassel, J., Mannucci, P. & Cazenave, J. P. (1995). Br. J. Haematol. 91, 434.  [CrossRef] [PubMed] [ISI]
Jin, L., Chen, J., Song, B., Chen, Z., Yang, S., Li, Q., Hu, D. & Xu, R. (2006). Bioorg. Med. Chem. Lett. 16, 5036-5040.  [CSD] [CrossRef] [PubMed] [ChemPort]
Krasovskii, A. N., Bulgakov, A. K., Andrushko, A. P., Krasovskii, I. A., Dyachenko, A. M., Bokun, A. A., Kravchenko, N. A. & Demchenko, A. M. (2000). Pharm. Chem. J. 34, 115-117.  [CrossRef] [ChemPort]
Lohaus, G., Dittmar, W. & Afric, S. (1968). Pat. 6 906, 036.
Lohaus, G., Dittmar, W. & Afric, S. (1970). Chem. Abstr. 73, 120508.
Mishra, L., Said, M. K., Itokawa, H. & Takeya, K. (1995). Bioorg. Med. Chem. Lett. 3, 1241-1245.  [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Suman, S. P. & Bahel, S. C. V. (1979). J. Indian Chem. Soc. 56, 712.
Todd, A. H. (1970a). UK Patent 1 203 149.
Todd, A. H. (1970b). Chem. Abstr. 73, 120509.
Umemura, K., Kawai, H., Ishihara, H. & Nakashima, M. (1995). Jpn J. Pharmacol. 76, 253-258.  [CrossRef]
Yao, S. K., Ober, J. C., Ferguson, J. J., Maffrand, J. P., Anderson, H. V., Buja, L. M. & Willerson, J. T. (1994). Am. J. Physiol. pp. H488-H493.
Youngdale, G. A. (1980). US Patent 4 288 440.
Youngdale, G. A. (1982). Chem. Abstr. 96, 6596.


Acta Cryst (2013). E69, o491-o492   [ doi:10.1107/S1600536813005837 ]

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