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Volume 69 
Part 5 
Page o797  
May 2013  

Received 9 April 2013
Accepted 19 April 2013
Online 27 April 2013

Key indicators
Single-crystal X-ray study
T = 90 K
Mean [sigma](C-C) = 0.003 Å
R = 0.045
wR = 0.124
Data-to-parameter ratio = 12.4
Details
Open access

Dimethyl 2-aminobiphenyl-4,4'-dicarboxylate

aDepartment of Chemistry and Biochemistry, University of Massachusetts Dartmouth, 285 Old Westport Road, North Dartmouth, MA 02747, USA, and bDepartment of Chemistry, University of California, San Diego, 9500 Gilman Drive, La Jolla, CA 92093, USA
Correspondence e-mail: dmanke@umassd.edu

The title compound, C16H15NO4, exhibits two near-planar aromatic ester groups with a maximum aryl-ester torsion angle of 1.9 (2)°. The dihedral angle between the benzene rings is 44.7 (1)°. In the crystal, N-H...O hydrogen bonding is observed along with C-H...O contacts, forming chanins along [101]. No [pi]-[pi] interactions were noted between the benzene rings.

Related literature

For the synthesis of the title compound, see: Olkhovik et al. (2008[Olkhovik, V. K., Vasilevskii, D. A., Pap, A. A., Kalechyts, G. V., Matveienko, Y. V., Baran, A. G., Halinouski, N. A. & Petushok, V. G. (2008). ARKIVOC, pp. 69-93.]). For the crystal structures of the parent dimethyl-4,4'-dicarboxylate and its structurally characterized amino derivatives, see: Ritzerfeld et al. (2009[Ritzerfeld, V., Pyrlik, A., Wang, Y. & Englert, U. (2009). Acta Cryst. E65, o1677.]); Nyburg et al. (1988[Nyburg, S. C., Prasad, L., Behnam, B. A. & Hall, D. M. (1988). J. Chem. Soc. Perkin Trans. 2, pp. 617-623.]). For metal-organic framework structures with this and related linkers, see: Deshpande et al. (2010[Deshpande, R. K., Minnaar, J. L. & Telfer, S. G. (2010). Angew. Chem. Int. Ed. 49, 4598-4602.]); Lun et al. (2011[Lun, D. J., Waterhouse, G. I. N. & Telfer, S. G. (2011). J. Am. Chem. Soc. 133, 5806-5809.]); Gupta et al. (2012[Gupta, A. S., Deshpande, R. K., Liu, L., Waterhouse, G. I. N. & Telfer, S. G. (2012). CrystEngComm, 14, 5701-5704.]); Sudik et al. (2005[Sudik, A. D., Millward, A. R., Ockwig, N. W., Cote, A. P., Kim, J. & Yaghi, O. M. (2005). J. Am. Chem. Soc. 127, 7110-7118.]).

[Scheme 1]

Experimental

Crystal data
  • C16H15NO4

  • Mr = 285.29

  • Monoclinic, P 21 /c

  • a = 12.955 (3) Å

  • b = 7.3460 (16) Å

  • c = 14.422 (3) Å

  • [beta] = 103.263 (10)°

  • V = 1336.0 (5) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 90 K

  • 0.28 × 0.12 × 0.06 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.972, Tmax = 0.994

  • 9113 measured reflections

  • 2463 independent reflections

  • 1785 reflections with I > 2[sigma](I)

  • Rint = 0.036

Refinement
  • R[F2 > 2[sigma](F2)] = 0.045

  • wR(F2) = 0.124

  • S = 1.01

  • 2463 reflections

  • 198 parameters

  • 2 restraints

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

  • [Delta][rho]max = 0.27 e Å-3

  • [Delta][rho]min = -0.35 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1NB...O2i 0.88 (1) 2.54 (2) 3.304 (3) 146 (2)
N1-H1NA...O4ii 0.88 (1) 2.33 (1) 3.147 (2) 155 (2)
C4-H4A...O2i 0.95 2.44 3.301 (3) 150
Symmetry codes: (i) -x, -y+2, -z; (ii) -x+1, -y+2, -z+1.

Data collection: APEX2 (Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FF2103 ).


Acknowledgements

RLL thanks the Jean Dreyfus Boissevain Lectureship for Undergraduate Institutions, the UMass Dartmouth Office of Undergraduate Research Award and the UMass Dartmouth Honors Summer Research Grant for funding. DRM gratefully acknowledges support from the UMass Dartmouth Chancellor's Research Fund and the Joseph P. Healey Endowment.

References

Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Deshpande, R. K., Minnaar, J. L. & Telfer, S. G. (2010). Angew. Chem. Int. Ed. 49, 4598-4602.  [CSD] [CrossRef] [ChemPort]
Gupta, A. S., Deshpande, R. K., Liu, L., Waterhouse, G. I. N. & Telfer, S. G. (2012). CrystEngComm, 14, 5701-5704.  [CrossRef]
Lun, D. J., Waterhouse, G. I. N. & Telfer, S. G. (2011). J. Am. Chem. Soc. 133, 5806-5809.  [CSD] [CrossRef] [ChemPort] [PubMed]
Nyburg, S. C., Prasad, L., Behnam, B. A. & Hall, D. M. (1988). J. Chem. Soc. Perkin Trans. 2, pp. 617-623.
Olkhovik, V. K., Vasilevskii, D. A., Pap, A. A., Kalechyts, G. V., Matveienko, Y. V., Baran, A. G., Halinouski, N. A. & Petushok, V. G. (2008). ARKIVOC, pp. 69-93.  [CrossRef]
Ritzerfeld, V., Pyrlik, A., Wang, Y. & Englert, U. (2009). Acta Cryst. E65, o1677.  [CSD] [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Sudik, A. D., Millward, A. R., Ockwig, N. W., Cote, A. P., Kim, J. & Yaghi, O. M. (2005). J. Am. Chem. Soc. 127, 7110-7118.  [CSD] [CrossRef] [PubMed] [ChemPort]


Acta Cryst (2013). E69, o797  [ doi:10.1107/S1600536813010775 ]

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