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Volume 69 
Part 10 
Pages o1526-o1527  
October 2013  

Received 27 July 2013
Accepted 5 September 2013
Online 12 September 2013

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.003 Å
R = 0.055
wR = 0.134
Data-to-parameter ratio = 18.5
Details
Open access

Dipentyl 2,6-diaminobenzo[1,2-b:4,5-b']difuran-3,7-dicarboxylate

aDipartimento di Ingegneria, Università di Napoli 'Parthenope', Centro Direzionale di Napoli, Isola C4, 80143 Napoli, Italy,bDipartimento di Scienze Chimiche, Università degli Studi di Napoli 'Federico II', Complesso di Monte S. Angelo, Via Cinthia, 80126 Napoli, Italy, and cIstituto di Biostrutture e Bioimmagini, CNR, Via Mezzocannone 16, 80134 Naples, Italy
Correspondence e-mail: giuseppina.roviello@uniparthenope.it, angela.tuzi@unina.it

The title compound, C22H28N2O6, crystallizes with one half-molecule in the independent unit, the molecule being located on an inversion centre. The penthyl groups are in the all-trans conformation and an almost planar conformation of the whole molecule is observed [maximum deviation from the least-squares plane through all non-H atoms is 0.0229 (17) Å for an N atom]. The amino groups are involved in intra- and intermolecular hydrogen bonds. Intramolecular hydrogen bonding involving the amino group and ester carbonyl helps to lock the syn conformation of the ester with respect to the amino group. In the crystal, N-H...O hydrogen bonding involving the amino group and the furan and ester carbonyl O atoms self-assembles the molecules into a two-dimensional hydrogen-bonded network parallel to (010) that displays interdigital packing sustained by alkyl-alkyl interactions.

Related literature

For the synthesis and properties of aminobenzodifurane derivatives, see: Caruso et al. (2009[Caruso, U., Panunzi, B., Roviello, G. N., Roviello, G., Tingoli, M. & Tuzi, A. (2009). C. R. Chim. 12, 622-634.]). For O- and N-rich aromatic heterocycles, see: Roviello et al. (2007[Roviello, A., Buono, A., Carella, A., Roviello, G., Cassinese, A., Barra, M. & Biasucci, M. (2007). J. Polym. Sci. Part A Polym. Chem. 45, 1758-1760.], 2012[Roviello, G. N., Roviello, G., Musumeci, D., Bucci, E. M. & Pedone, C. (2012). Amino Acids, 43, 1615-1623.]). For molecules with optical and opto-electronical properties, see: Carella et al. (2012[Carella, A., Borbone, F., Roviello, A., Roviello, G., Tuzi, A., Kravinsky, A., Shikler, R., Cantele, G. & Ninno, D. (2012). Dyes Pigm. 95, 116-125.]); Centore et al. (2007[Centore, R., Riccio, P., Fusco, S., Carella, A., Quatela, A., Schutzmann, S., Stella, F. & De Matteis, F. (2007). J. Polym. Sci. Part A Polym. Chem. 45, 2719-2725.]); Roviello et al. (2009[Roviello, A., Borbone, F., Carella, A., Diana, R., Roviello, G., Panunzi, B., Ambrosio, A. & Maddalena, P. (2009). J. Polym. Sci. Part A Polym. Chem. 47, 2677-2689.]); Ricciotti et al. (2013[Ricciotti, L., Borbone, F., Carella, A., Centore, R., Roviello, A., Barra, M., Roviello, G., Ferone, C., Minarini, C. & Morvillo, P. (2013). J. Polym. Sci. Part A Polym. Chem. doi:10.1002/pola.26849.]); Vitaliano et al. (2009[Vitaliano, R., Fratoddi, I., Venditti, I., Roviello, G., Battocchio, C., Polzonetti, G. & Russo, M. V. (2009). J. Phys. Chem. A, 113, 14730-14740.]). For hydrogen bonding in heterocycles, see: Centore et al. (2013a[Centore, R., Piccialli, V. & Tuzi, A. (2013a). Acta Cryst. E69, o667-o668.],b[Centore, R., Piccialli, V. & Tuzi, A. (2013b). Acta Cryst. E69, o802-o803.]).

[Scheme 1]

Experimental

Crystal data
  • C22H28N2O6

  • Mr = 416.46

  • Monoclinic, P 21 /c

  • a = 8.267 (1) Å

  • b = 7.994 (1) Å

  • c = 17.582 (3) Å

  • [beta] = 98.98 (2)°

  • V = 1147.7 (3) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 173 K

  • 0.50 × 0.04 × 0.01 mm

Data collection
  • Bruker-Nonius KappaCCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2001[Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.957, Tmax = 0.999

  • 11093 measured reflections

  • 2626 independent reflections

  • 1258 reflections with I > 2[sigma](I)

  • Rint = 0.096

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

  • wR(F2) = 0.134

  • S = 0.93

  • 2626 reflections

  • 142 parameters

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

  • [Delta][rho]max = 0.19 e Å-3

  • [Delta][rho]min = -0.20 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1A...O2i 0.83 (2) 2.11 (2) 2.935 (3) 171 (2)
N1-H1B...O1ii 0.84 (2) 2.34 (2) 3.066 (2) 144 (2)
N1-H1B...O2 0.84 (2) 2.41 (2) 2.942 (3) 122.2 (18)
Symmetry codes: (i) [-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) [-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: COLLECT (Nonius, 1999[Nonius, B. V. (1999). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: DIRAX/LSQ (Duisenberg et al., 2000[Duisenberg, A. J. M., Hooft, R. W. W., Schreurs, A. M. M. & Kroon, J. (2000). J. Appl. Cryst. 33, 893-898.]); data reduction: EVALCCD (Duisenberg et al., 2003[Duisenberg, A. J. M., Kroon-Batenburg, L. M. J. & Schreurs, A. M. M. (2003). J. Appl. Cryst. 36, 220-229.]); program(s) used to solve structure: SIR97 (Altomare et al., 1999[Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.]); 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, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and Mercury (Macrae et al., 2006[Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: DS2234 ).


Acknowledgements

The authors thank the Centro Interdipartimentale di Metodologie Chimico-Fisiche, Università degli Studi di Napoli "Federico II" for the X-ray facilities.

References

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Centore, R., Piccialli, V. & Tuzi, A. (2013a). Acta Cryst. E69, o667-o668.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Centore, R., Piccialli, V. & Tuzi, A. (2013b). Acta Cryst. E69, o802-o803.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Centore, R., Riccio, P., Fusco, S., Carella, A., Quatela, A., Schutzmann, S., Stella, F. & De Matteis, F. (2007). J. Polym. Sci. Part A Polym. Chem. 45, 2719-2725.  [CrossRef] [ChemPort]
Duisenberg, A. J. M., Hooft, R. W. W., Schreurs, A. M. M. & Kroon, J. (2000). J. Appl. Cryst. 33, 893-898.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Duisenberg, A. J. M., Kroon-Batenburg, L. M. J. & Schreurs, A. M. M. (2003). J. Appl. Cryst. 36, 220-229.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Nonius, B. V. (1999). COLLECT. Nonius BV, Delft, The Netherlands.
Ricciotti, L., Borbone, F., Carella, A., Centore, R., Roviello, A., Barra, M., Roviello, G., Ferone, C., Minarini, C. & Morvillo, P. (2013). J. Polym. Sci. Part A Polym. Chem. doi:10.1002/pola.26849.
Roviello, A., Borbone, F., Carella, A., Diana, R., Roviello, G., Panunzi, B., Ambrosio, A. & Maddalena, P. (2009). J. Polym. Sci. Part A Polym. Chem. 47, 2677-2689.  [CrossRef] [ChemPort]
Roviello, A., Buono, A., Carella, A., Roviello, G., Cassinese, A., Barra, M. & Biasucci, M. (2007). J. Polym. Sci. Part A Polym. Chem. 45, 1758-1760.  [CrossRef] [ChemPort]
Roviello, G. N., Roviello, G., Musumeci, D., Bucci, E. M. & Pedone, C. (2012). Amino Acids, 43, 1615-1623.  [Web of Science] [CSD] [CrossRef] [ChemPort] [PubMed]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Vitaliano, R., Fratoddi, I., Venditti, I., Roviello, G., Battocchio, C., Polzonetti, G. & Russo, M. V. (2009). J. Phys. Chem. A, 113, 14730-14740.  [Web of Science] [CrossRef] [PubMed] [ChemPort]


Acta Cryst (2013). E69, o1526-o1527   [ doi:10.1107/S160053681302480X ]

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