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Volume 68 
Part 12 
Page o3411  
December 2012  

Received 31 October 2012
Accepted 16 November 2012
Online 24 November 2012

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.003 Å
R = 0.052
wR = 0.151
Data-to-parameter ratio = 18.2
Details
Open access

Morpholine-4-nitrophenol (1/2)

aDepartment of Physics, Anna University, Chennai 600 025, India, and bCentre of Advanced Study in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai 600 025, India
Correspondence e-mail: shirai2011@gmail.com

In the title adduct, 2C6H5NO3·C4H9NO, the morpholine ring adopts a chair conformation. The dihedral angle between the two nitrophenol rings is 69.47 (9)°. The nitro groups attached to the benzene rings make dihedral angles of 3.37 (16) and 3.14 (13)° in the two molecules of nitrophenol. The crystal structure is stabilized by N-H...O, O-H...N and O-H...O hydrogen bonds and further consolidated by C-H...O interactions, resulting in a three-dimensional network.

Related literature

For the biological activity and synthesis of 4-(4-nitrophenyl)-morpholine derivatives, see: Wang et al. (2010[Wang, S. D., Midgley, C. A., Scaerou, F., Grabarek, J. B., Griffiths, G., Jackson, W., Kontopidis, G., McClue, S. J., McInnes, C., Meades, C., Mezna, M., Plater, A., Stuart, I., Thomas, M. P., Wood, G., Clarke, R. G., Blake, D. G., Zheleva, D. I., Lane, D. P., Jackson, R. C., Glover, D. M. & Fischer, P. M. (2010). J. Med. Chem.. 53, 4367-4378.]). For a related structure, see: Wang et al. (2012[Wang, L.-J., Li, W.-W., Yang, S.-Y. & Yang, L. (2012). Acta Cryst. E68, o1235.]).

[Scheme 1]

Experimental

Crystal data
  • 2C6H5NO3·C4H9NO

  • Mr = 365.34

  • Monoclinic, P 21 /c

  • a = 18.0381 (7) Å

  • b = 5.5673 (2) Å

  • c = 17.4910 (7) Å

  • [beta] = 91.606 (3)°

  • V = 1755.82 (12) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.11 mm-1

  • T = 293 K

  • 0.35 × 0.30 × 0.25 mm

Data collection
  • Bruker SMART APEXII area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.963, Tmax = 0.973

  • 16662 measured reflections

  • 4354 independent reflections

  • 2987 reflections with I > 2[sigma](I)

  • Rint = 0.027

Refinement
  • R[F2 > 2[sigma](F2)] = 0.052

  • wR(F2) = 0.151

  • S = 1.05

  • 4354 reflections

  • 239 parameters

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

  • [Delta][rho]max = 0.45 e Å-3

  • [Delta][rho]min = -0.30 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N3-H3B...O7i 0.77 (2) 2.46 (2) 3.000 (2) 129 (2)
N3-H3B...O4ii 0.77 (2) 2.36 (2) 3.032 (2) 147 (2)
C14-H14B...O4ii 0.97 2.55 3.322 (3) 136
O3-H3A...O6 0.82 1.77 2.590 (2) 173
O6-H6A...N3 0.82 1.93 2.607 (2) 140
C6-H6...O2iii 0.93 2.53 3.424 (3) 161
C14-H14A...O5iv 0.97 2.49 3.403 (3) 157
C15-H15B...O1v 0.97 2.48 3.400 (3) 159
C16-H16B...O2vi 0.97 2.56 3.441 (3) 152
Symmetry codes: (i) x, y+1, z; (ii) [x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]; (iii) -x+1, -y+2, -z; (iv) [-x, y-{\script{3\over 2}}, -z+{\script{1\over 2}}]; (v) -x+1, -y, -z; (vi) -x+1, -y+1, -z.

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). 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: ORTEP-3 (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: SHELXL97 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: PV2605 ).


Acknowledgements

The authors thank the TBI X-ray facility, CAS in Crystallography and Biophysics, University of Madras, India, for the data collection and TS also thanks the DST for an Inspire fellowship.

References

Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Wang, L.-J., Li, W.-W., Yang, S.-Y. & Yang, L. (2012). Acta Cryst. E68, o1235.  [CSD] [CrossRef] [details]
Wang, S. D., Midgley, C. A., Scaerou, F., Grabarek, J. B., Griffiths, G., Jackson, W., Kontopidis, G., McClue, S. J., McInnes, C., Meades, C., Mezna, M., Plater, A., Stuart, I., Thomas, M. P., Wood, G., Clarke, R. G., Blake, D. G., Zheleva, D. I., Lane, D. P., Jackson, R. C., Glover, D. M. & Fischer, P. M. (2010). J. Med. Chem.. 53, 4367-4378.  [ISI] [CrossRef] [ChemPort] [PubMed]


Acta Cryst (2012). E68, o3411  [ doi:10.1107/S1600536812047174 ]

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