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Volume 69 
Part 5 
Pages o675-o676  
May 2013  

Received 12 March 2013
Accepted 27 March 2013
Online 10 April 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.004 Å
R = 0.065
wR = 0.210
Data-to-parameter ratio = 15.3
Details
Open access

N,N-Diphenyl-4-(1H-pyrrolo[1,2-f][1,10]phenanthrolin-2-yl)aniline ethanol monosolvate

aDeparment of Chemistry, Anhui University, Hefei 230601, People's Republic of China, and bKey Laboratory of Functional Inorganic Materials, Chemistry, Hefei 230601, People's Republic of China
Correspondence e-mail: yptian@ahu.edu.cn

The title compound, C32H21N4·C2H5OH, crystallized as an ethanol monosolvate. In the molecule of this phenanthroline derivative, the pyridine rings are almost coplanar, making a dihedral angle of 1.54 (13)°. The triphenylamine group, introduced as an electron donor, shows a propeller-type structure, and the dihedral angles between the benzene rings are 68.71 11), 63.92 (16) and 70.81 (15)°. In the crystal, the phenanthroline molecules are linked via the solvent molecule by N-H...O, O-H...N and C-H...O hydrogen bonds, leading to the formation of zigzag chains propagating along [010]. These chains are linked via C-H...N hydrogen bonds, forming undulating two-dimensional networks extending in the a- and b-axis directions.

Related literature

For background to imidazo[4,5-f]-1,10-phenanthroline compounds, see: Li et al. (2012[Li, S. S., Zhang, C., Huang, S. Y., Hu, F., Yin, J. & Liu, S. H. (2012). RSC Advances, 2, 4215-4219.]). For metal complexes and binding studies, see: Ma et al. (2009[Ma, Y.-Z., Yin, H.-J. & Wang, K.-Z. (2009). J. Phys. Chem. B, 113, 11039-11047.]); Xu et al. (2012[Xu, F., Peng, Y.-X., Hu, B., Tao, T. & Huang, W. (2012). CrystEngComm, 14, 8023-8032.]); Zheng et al. (2013[Zheng, Z., Zhang, Q., Yu, Z. P., Yang, M. D., Zhou, H. P., Wu, J. Y. & Tian, Y. P. (2013). J. Mater. Chem. C, 1, 822-830.]). For the crystal structures of related compounds, see: Sun et al. (2009[Sun, B., Guan, J.-X., Xu, L., Yu, B.-L. & Jiang, L. (2009). Inorg. Chem. 48, 4637-4639.]); Eseola et al. (2012[Eseola, A. O., Adepitan, O., Görls, H. & Plass, W. (2012). New J. Chem. 36, 891-902.]); Bhat et al. (2011[Bhat, S. S., Kumbhar, A. A., Heptullah, H. & Khan, A. A. (2011). Inorg. Chem. 50, 545-558.]).

[Scheme 1]

Experimental

Crystal data
  • C32H21N4·C2H6O

  • Mr = 507.60

  • Monoclinic, P 21 /c

  • a = 9.716 (4) Å

  • b = 10.690 (4) Å

  • c = 27.017 (10) Å

  • [beta] = 92.317 (4)°

  • V = 2803.8 (18) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.07 mm-1

  • T = 296 K

  • 0.20 × 0.20 × 0.10 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2007[Bruker (2007). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.985, Tmax = 0.993

  • 20210 measured reflections

  • 5216 independent reflections

  • 3870 reflections with I > 2[sigma](I)

  • Rint = 0.024

Refinement
  • R[F2 > 2[sigma](F2)] = 0.065

  • wR(F2) = 0.210

  • S = 1.02

  • 5216 reflections

  • 340 parameters

  • 6 restraints

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

  • [Delta][rho]max = 0.51 e Å-3

  • [Delta][rho]min = -0.50 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N3-H3N...O1 0.94 (3) 1.84 (3) 2.777 (3) 175 (2)
O1-H1O1...N1i 0.82 2.15 2.819 (3) 139
O1-H1O1...N2i 0.82 2.38 3.087 (3) 145
C16-H16...O1 0.93 2.54 3.419 (4) 157
C3-H3...N2i 0.93 2.59 3.310 (4) 135
Symmetry code: (i) [-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2007[Bruker (2007). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). SADABS, SMART and SAINT. 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.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SU2573 ).


Acknowledgements

This work was supported by a grant from the National Natural Science Foundation of China (21071001, 21271004, 21201005, 21101069, 51142011), the Natural Science Foundation of Anhui Province (1208085MB22) and the Ministry of Education of China Funded Projects Focused on Returned Overseas Scholars.

References

Bhat, S. S., Kumbhar, A. A., Heptullah, H. & Khan, A. A. (2011). Inorg. Chem. 50, 545-558.  [ISI] [CSD] [CrossRef] [ChemPort]
Bruker (2007). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Eseola, A. O., Adepitan, O., Görls, H. & Plass, W. (2012). New J. Chem. 36, 891-902.  [ISI] [CSD] [CrossRef] [ChemPort]
Li, S. S., Zhang, C., Huang, S. Y., Hu, F., Yin, J. & Liu, S. H. (2012). RSC Advances, 2, 4215-4219.  [CrossRef] [ChemPort]
Ma, Y.-Z., Yin, H.-J. & Wang, K.-Z. (2009). J. Phys. Chem. B, 113, 11039-11047.  [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [ChemPort] [details]
Sun, B., Guan, J.-X., Xu, L., Yu, B.-L. & Jiang, L. (2009). Inorg. Chem. 48, 4637-4639.  [ISI] [CSD] [CrossRef] [PubMed] [ChemPort]
Xu, F., Peng, Y.-X., Hu, B., Tao, T. & Huang, W. (2012). CrystEngComm, 14, 8023-8032.  [ISI] [CSD] [CrossRef] [ChemPort]
Zheng, Z., Zhang, Q., Yu, Z. P., Yang, M. D., Zhou, H. P., Wu, J. Y. & Tian, Y. P. (2013). J. Mater. Chem. C, 1, 822-830.  [CrossRef] [ChemPort]


Acta Cryst (2013). E69, o675-o676   [ doi:10.1107/S1600536813008477 ]

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