[Journal logo]

Volume 69 
Part 11 
Page o1697  
November 2013  

Received 9 October 2013
Accepted 15 October 2013
Online 23 October 2013

Key indicators
Single-crystal X-ray study
T = 153 K
Mean [sigma](C-C) = 0.004 Å
R = 0.057
wR = 0.132
Data-to-parameter ratio = 17.9
Details
Open access

2-[(1H-Pyrrol-2-yl)meth­yl]-1H-pyrrole

aCenter for Chemical Analysis, Korea Research Institute of Chemical Technology, 141 Gajeongro, Yuseong, Daejeon 305-600, Republic of Korea,bDepartment of Bio and Chemical Engineering, Hongik University at Sejong, 2639 Sejongro, Jochiwon, Sejong 339-701, Republic of Korea, and cDepartment of Chemistry, The University of Texas, 105 E. 24th St STOP A5300, Austin, TX 78712-1224, USA
Correspondence e-mail: sessler@mail.utexas.edu, kjhwang@hongik.ac.kr

In the title compound, C9H10N2, the two pyrrole ring planes are twisted by a dihedral angle of 69.07 (16)° and the C-C-C methane angle is 115.1 (2)°. In the crystal, mol­ecules are connected into layers in the bc plane by N-H...[pi] inter­actions.

Related literature

For synthesis of symmetric and non-symmetric porphyrins, see: Shanmugathasan et al. (2000[Shanmugathasan, S., Edwards, C. & Boyle, R. W. (2000). Tetrahedron, 56, 1025-1046.]); Bonifazi et al. (2005[Bonifazi, D., Accorsi, G., Armaroli, N., Song, F., Palkar, A., Echegoyen, L., Scholl, M., Seiler, P., Jaun, B. & Diederich, F. (2005). Helv. Chim. Acta, 88, 1839-1884.]); Fendt et al. (2009[Fendt, L.-A., Stohr, M., Wintjes, N., Enache, M., Jung, T. A. & Diederich, F. (2009). Chem. Eur. J. 15, 11139-11150.]). For their applications as organometallic ligands, see: Ganesan et al. (2001[Ganesan, M., Lalonde, M. P., Gambarotta, S. & Yap, G. P. A. (2001). Organometallics, 20, 2443-2445.]); Gao et al. (2004[Gao, G., Korobkov, I. & Gambarotta, S. (2004). Inorg. Chem. 43, 1108-1115.]).

[Scheme 1]

Experimental

Crystal data
  • C9H10N2

  • Mr = 146.19

  • Monoclinic, P 21

  • a = 6.048 (3) Å

  • b = 7.312 (4) Å

  • c = 9.024 (5) Å

  • [beta] = 100.78 (1)°

  • V = 392.0 (4) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.08 mm-1

  • T = 153 K

  • 0.32 × 0.08 × 0.06 mm

Data collection
  • Rigaku SCX-Mini diffractometer with Mercury 2 CCD

  • Absorption correction: multi-scan (ABSCOR; Higashi, 1995[Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.976, Tmax = 0.996

  • 4179 measured reflections

  • 1786 independent reflections

  • 1374 reflections with I > 2[sigma](I)

  • Rint = 0.063

Refinement
  • R[F2 > 2[sigma](F2)] = 0.057

  • wR(F2) = 0.132

  • S = 1.05

  • 1786 reflections

  • 100 parameters

  • 61 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.19 e Å-3

  • [Delta][rho]min = -0.23 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the N1/C1-C4 and N2/C6-C9 rings, respectively.

D-H...A D-H H...A D...A D-H...A
N1-H1N...Cg1i 0.88 2.53 3.357 (3) 156
N2-H2N...Cg2ii 0.88 2.53 3.363 (3) 159
Symmetry codes: (i) [-x, y-{\script{1\over 2}}, -z+1]; (ii) [-x, y-{\script{1\over 2}}, -z].

Data collection: CrystalClear (Molecular Structure Corporation & Rigaku, 2008[Molecular Structure Corporation & Rigaku (2008). CrystalClear. MSC, The Woodlands, Texas, USA, and Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear; data reduction: CrystalClear; 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: SHELXTL/PC (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL/PC; software used to prepare material for publication: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK5264 ).


Acknowledgements

This research was supported by the Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education (NRF-2013R1A1A2012154). The work in Austin was supported by the US National Science Foundation (grant No. CHE-1057904 to JLS and CHE-0741973 for the diffractometer). KJH was on sabbatical leave at the University of Texas, Austin, during 2012.

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.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Bonifazi, D., Accorsi, G., Armaroli, N., Song, F., Palkar, A., Echegoyen, L., Scholl, M., Seiler, P., Jaun, B. & Diederich, F. (2005). Helv. Chim. Acta, 88, 1839-1884.  [CSD] [CrossRef] [ChemPort]
Fendt, L.-A., Stohr, M., Wintjes, N., Enache, M., Jung, T. A. & Diederich, F. (2009). Chem. Eur. J. 15, 11139-11150.  [CrossRef] [PubMed] [ChemPort]
Ganesan, M., Lalonde, M. P., Gambarotta, S. & Yap, G. P. A. (2001). Organometallics, 20, 2443-2445.  [CSD] [CrossRef] [ChemPort]
Gao, G., Korobkov, I. & Gambarotta, S. (2004). Inorg. Chem. 43, 1108-1115.  [Web of Science] [CSD] [CrossRef] [PubMed] [ChemPort]
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.
Molecular Structure Corporation & Rigaku (2008). CrystalClear. MSC, The Woodlands, Texas, USA, and Rigaku Corporation, Tokyo, Japan.
Shanmugathasan, S., Edwards, C. & Boyle, R. W. (2000). Tetrahedron, 56, 1025-1046.  [Web of Science] [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1697  [ doi:10.1107/S1600536813028365 ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.