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Volume 68 
Part 12 
Pages o3447-o3448  
December 2012  

Received 15 November 2012
Accepted 21 November 2012
Online 24 November 2012

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.002 Å
R = 0.045
wR = 0.113
Data-to-parameter ratio = 13.4
Details
Open access

N-(2-Oxo-2H-chromen-3-yl)cyclohexanecarboxamide

aDepartment of Organic Chemistry, University of Santiago de Compostela, Santiago de Compostela, Spain
Correspondence e-mail: mariacmatos@gmail.com

In the title compound, C16H17NO3, the coumarin moiety is essentially planar [maximum deviation from the mean plane formed by the C and O atoms of the coumarin = 0.0183 (12) Å] and that the cyclohexane ring adopts the usual chair conformation. The dihedral angle between the mean plane of the coumarin residue and the plane of the amide residue (defined as the N, C and O atoms) is 18.9 (2)°. There are two intramolecular hydrogen bonds involving the amide group. In one, the N atom acts as donor to the ketonic O atom and in the other, the amide O atom acts as acceptor of a C-H group of the coumarin. In the crystal, molecules are linked into inversion dimers by pairs of N-H...O contacts and these dimers are linked into pairs by weak C-H...O hydrogen bonds. The combination of these interactions creates a chain of rings which runs parallel to [2-10]. C-H...[pi] and [pi]-[pi] [centroid-centroid distance = 3.8654 (10) Å] interactions are also observed.

Related literature

For the synthesis of the title compound, see: Viña, Matos, Ferino et al. (2012[Viña, D., Matos, M. J., Ferino, G., Cadoni, E., Laguna, R., Borges, F., Uriarte, E. & Santana, L. (2012). Chem. Med. Chem. 7, 464-470.]); Viña, Matos, Yáñez et al. (2012[Viña, D., Matos, M. J., Yáñez, M., Santana, L. & Uriarte, E. (2012). MedChemComm, 3, 213-218.]). For the biological activity of coumarin derivatives, see: Borges et al. (2009[Borges, F., Roleira, F., Milhazes, N., Uriarte, E. & Santana, L. (2009). Front. Med. Chem. 4, 23-85.]); Matos et al. (2009[Matos, M. J., Viña, D., Quezada, E., Picciau, C., Delogu, G., Orallo, F., Santana, L. & Uriarte, E. (2009). Bioorg. Med. Chem. Lett. 19, 3268-3270.], 2010[Matos, M. J., Viña, D., Janeiro, P., Borges, F., Santana, L. & Uriarte, E. (2010). Bioorg. Med. Chem. Lett. 20, 5157-5160.]); Matos, Santana et al. (2011[Matos, M. J., Santana, L., Uriarte, E., Delogu, G., Corda, M., Fadda, M. B., Era, B. & Fais, A. (2011). Bioorg. Med. Chem. Lett. 21, 3342-3345.]); Matos, Terán et al. (2011[Matos, M. J., Terán, C., Pérez-Castillo, Y., Uriarte, E., Santana, L. & Viña, D. (2011). J. Med. Chem. 54, 7127-7137.]). For graph-set analysis of hydrogen bonds, see: Bernstein et al., (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.])

[Scheme 1]

Experimental

Crystal data
  • C16H17NO3

  • Mr = 271.31

  • Triclinic, [P \overline 1]

  • a = 6.4486 (6) Å

  • b = 9.6324 (11) Å

  • c = 11.0837 (11) Å

  • [alpha] = 83.061 (6)°

  • [beta] = 89.134 (5)°

  • [gamma] = 73.987 (5)°

  • V = 656.79 (12) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 100 K

  • 0.48 × 0.45 × 0.09 mm

Data collection
  • Bruker X8 APEXII KappaCCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2012[Bruker (2012). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.910, Tmax = 1.000

  • 9698 measured reflections

  • 2487 independent reflections

  • 1834 reflections with I > 2[sigma](I)

  • Rint = 0.044

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

  • wR(F2) = 0.113

  • S = 1.06

  • 2487 reflections

  • 185 parameters

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

  • [Delta][rho]max = 0.20 e Å-3

  • [Delta][rho]min = -0.25 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the O1/C2-C5/C10 and C5-C10 rings, respectively.

D-H...A D-H H...A D...A D-H...A
N12-H12...O11 0.87 (2) 2.346 (19) 2.6990 (18) 104.7 (14)
N12-H12...O11i 0.87 (2) 2.098 (18) 2.9303 (16) 160.8 (17)
C4-H4...O14 0.95 2.37 2.9094 (19) 115
C7-H7...O14ii 0.95 2.57 3.473 (2) 158
C16-H16B...Cg1iii 0.99 2.81 3.5732 (17) 134
C17-H17B...Cg2iii 0.99 2.70 3.5876 (19) 149
Symmetry codes: (i) -x+1, -y, -z; (ii) -x-1, -y+1, -z; (iii) -x, -y, -z.

Data collection: APEX2 (Bruker, 2012[Bruker (2012). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2012[Bruker (2012). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); 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: GO2076 ).


Acknowledgements

This work was supported by funds of Xunta da Galicia (09CSA030203PR), Ministerio de Sanidad y Consumo (PS09/00501) and Fundação para a Ciência e Tecnologia (SFRH/BD/61262/2009).

References

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.  [ISI] [CrossRef] [ChemPort] [details]
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Borges, F., Roleira, F., Milhazes, N., Uriarte, E. & Santana, L. (2009). Front. Med. Chem. 4, 23-85.
Bruker (2012). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Matos, M. J., Santana, L., Uriarte, E., Delogu, G., Corda, M., Fadda, M. B., Era, B. & Fais, A. (2011). Bioorg. Med. Chem. Lett. 21, 3342-3345.  [CrossRef] [ChemPort] [PubMed]
Matos, M. J., Terán, C., Pérez-Castillo, Y., Uriarte, E., Santana, L. & Viña, D. (2011). J. Med. Chem. 54, 7127-7137.  [ISI] [CrossRef] [ChemPort] [PubMed]
Matos, M. J., Viña, D., Janeiro, P., Borges, F., Santana, L. & Uriarte, E. (2010). Bioorg. Med. Chem. Lett. 20, 5157-5160.  [CrossRef] [ChemPort] [PubMed]
Matos, M. J., Viña, D., Quezada, E., Picciau, C., Delogu, G., Orallo, F., Santana, L. & Uriarte, E. (2009). Bioorg. Med. Chem. Lett. 19, 3268-3270.  [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Viña, D., Matos, M. J., Ferino, G., Cadoni, E., Laguna, R., Borges, F., Uriarte, E. & Santana, L. (2012). Chem. Med. Chem. 7, 464-470.  [PubMed]
Viña, D., Matos, M. J., Yáñez, M., Santana, L. & Uriarte, E. (2012). MedChemComm, 3, 213-218.


Acta Cryst (2012). E68, o3447-o3448   [ doi:10.1107/S1600536812047903 ]

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