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Volume 69 
Part 6 
Page o902  
June 2013  

Received 10 April 2013
Accepted 9 May 2013
Online 18 May 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.002 Å
R = 0.043
wR = 0.106
Data-to-parameter ratio = 22.9
Details
Open access

(Z)-N-tert-Butyl-2-(4-methoxyanilino)-N'-(4-methoxyphenyl)-2-phenylacetimidamide

aDepartment of Chemistry and Biochemistry, 1306 E University Boulevard, The University of Arizona, Tucson, AZ 85721, USA,bCollege of Pharmacy, Department of Pharmacology and Toxicology, The University of Arizona, Tucson, AZ 85721, USA, and cBio5 Oro Valley, The University of Arizona, Oro Valley, AZ 85737, USA
Correspondence e-mail: suer@email.arizona.edu

In the crystal of the title compound, C26H31N3O2, pairs of N-H...O hydrogen bonds link molecules, forming inversion dimers, which enclose an R22(20) ring motif. One N atom does not form hydrogen bonds and lies in a hydrophobic pocket with closest intermolecular contacts of 4.196 (2) and 4.262 (2) Å.

Related literature

For the synthesis of the title compound, and a discussion of the use of the three-component Ugi reaction to synthesize amidines, see: Saha et al. (2013[Saha, B., Frett, B., Wang, Y. & Li, H.-Y. (2013). Tetrahedron Lett. 54, 2340-2343.]).

[Scheme 1]

Experimental

Crystal data
  • C26H31N3O2

  • Mr = 417.54

  • Triclinic, [P \overline 1]

  • a = 10.0804 (17) Å

  • b = 10.5784 (17) Å

  • c = 11.1573 (18) Å

  • [alpha] = 80.982 (4)°

  • [beta] = 85.152 (4)°

  • [gamma] = 80.270 (4)°

  • V = 1156.1 (3) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.08 mm-1

  • T = 100 K

  • 0.20 × 0.20 × 0.10 mm

Data collection
  • Bruker Kappa APEXII DUO CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.89, Tmax = 0.99

  • 32612 measured reflections

  • 6607 independent reflections

  • 5476 reflections with I > 2[sigma](I)

  • Rint = 0.019

Refinement
  • R[F2 > 2[sigma](F2)] = 0.043

  • wR(F2) = 0.106

  • S = 0.94

  • 6607 reflections

  • 289 parameters

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

  • [Delta][rho]max = 0.36 e Å-3

  • [Delta][rho]min = -0.38 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N2-H2...O1i 0.887 (15) 2.328 (15) 3.1698 (13) 158.5 (12)
Symmetry code: (i) -x+1, -y+2, -z+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: 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.]) and OLEX2 (Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]); 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: 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: PK2477 ).


Acknowledgements

The Bruker Kappa APEXII DUO was purchased with funding from NSF grant CHE-0741837. The work was supported by start-up funds from the University of Arizona to HYL.

References

Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.  [ISI] [CrossRef] [ChemPort] [details]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
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.  [ISI] [CrossRef] [ChemPort] [details]
Saha, B., Frett, B., Wang, Y. & Li, H.-Y. (2013). Tetrahedron Lett. 54, 2340-2343.  [ISI] [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o902  [ doi:10.1107/S1600536813012877 ]

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