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Volume 69 
Part 10 
Pages o1572-o1573  
October 2013  

Received 12 September 2013
Accepted 17 September 2013
Online 21 September 2013

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.002 Å
Disorder in main residue
R = 0.042
wR = 0.116
Data-to-parameter ratio = 12.4
Details
Open access

3-(1H-Imidazol-1-yl)propanaminium picrate

aDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India, and bDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA
Correspondence e-mail: jjasinski@keene.edu

In the title salt [systematic name: 3-(1H-imidazol-1-yl)propanaminium 2,4,6-trinitrophenolate], C6H12N3+·C6H2N3O7-, there are five independent cation-anion pairs (A, B, C, D, E) in the asymmetric unit. In the cation, the ammonium group is protonated with the aminopropyl group nearly at right angles to the mean plane of the imidazole ring showing C-N-C-C torsion angles ranging from 79.6 (2) to 99.79 (19)° in the five cations. The nitro groups in the anion are twisted from the benzene mean plane with maximum dihedral angles subtended by nitro substituents ortho to the phenolate O atom of 26.0 (2) and 37.3 (7) (A), 28.9 (5) and 35.3 (1) (B), 34.7 (7) and 36.9 (7) (C), 14.7 (4) and 36.9 (2) (D) and 33.1 (1) and 35.4 (3)° (E). In contrast, the nitro groups in the para positions lie much closer to the aromatic ring plane, subtending dihedral angles of 1.8 (3) (A), 3.5 (3) (B), 6.03 (C), 2.1 (3) (D) and 7.7 (1)° (E). Disorder is observed for one O atom of an ortho nitro group in anion D with an occupancy ratio of 0.53 (5):0.47 (5). In the crystal, N-H...O cation-anion and N-H...N cation-cation hydrogen bonds are observed, linking the ions into chains along [010]. In addition, weak C-H...O cation-anion interactions occur.

Related literature

For pharmacological properties of imidazole compounds, see: Lombardino & Wiseman (1974[Lombardino, J. G. & Wiseman, E. H. (1974). J. Med. Chem. 17, 1182-1188.]). For applications of substituted imidazoles, see: Maier et al. (1989a[Maier, T., Schmierer, R., Bauer, K., Bieringer, H., Buerstell, H. & Sachse, B. (1989a). US Patent 4 820 335.],b[Maier, T., Schmierer, R., Bauer, K., Bieringer, H., Buerstell, H. & Sachse, B. (1989b). Chem. Abstr. 111, 19494.]). For imidazole derivatives as anticancer agents, see: Krezel (1998[Krezel, I. (1998). Farmaco, 53, 342-345.]). For electrostatic or hydrogen-bonding interactions in picric acid charge-transfer complexes, see: In et al. (1997[In, Y., Nagata, H., Doi, M., Ishida, T. & Wakahara, A. (1997). Acta Cryst. C53, 367-369.]). For imidazolium-based cation picrate salts as good candidates for energetic ionic salts, see: Jin et al. (2005[Jin, C. M., Ye, C., Piekarski, C., Twamley, B. & Shreeve, J. M. (2005). Eur. J. Inorg. Chem. pp. 3760-3767.]). For the crystal structure of imidazolium picrate, see: Soriano-García et al. (1990[Soriano-García, M., Schatz-Levine, M., Toscano, R. A. & Villena Iribe, R. (1990). Acta Cryst. C46, 1556-1558.]) and for the structures of picrates of some other imidazole derivatives, see: Du & Zhao (2003[Du, M. & Zhao, X.-J. (2003). Acta Cryst. E59, o1898-o1900.]); Dutkiewicz et al. (2011[Dutkiewicz, G., Samshuddin, S., Narayana, B., Yathirajan, H. S. & Kubicki, M. (2011). Acta Cryst. E67, o235.]); MacDonald et al. (2005[MacDonald, J., Yigit, M. V. & Mychajlonka, K. (2005). Cryst. Growth Des. 5, 2248-2255.]); Nardelli et al. (1987[Nardelli, M., Pelizzi, G., Vitali, F., Bordi, F., Plazzi, P. V. & Vitali, T. (1987). Acta Cryst. C43, 507-514.]); Pi et al. (2009[Pi, M., Liu, X.-L., Xu, J.-J. & Jin, C.-M. (2009). Acta Cryst. E65, o2386.]). For standard bond lengths, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data
  • C6H12N3+·C6H2N3O7-

  • Mr = 354.29

  • Monoclinic, P 21 /n

  • a = 11.98275 (18) Å

  • b = 38.5234 (6) Å

  • c = 16.4239 (2) Å

  • [beta] = 94.1970 (14)°

  • V = 7561.2 (2) Å3

  • Z = 20

  • Cu K[alpha] radiation

  • [mu] = 1.13 mm-1

  • T = 173 K

  • 0.21 × 0.17 × 0.08 mm

Data collection
  • Agilent Xcalibur (Eos, Gemini) diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012[Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.]) Tmin = 0.870, Tmax = 1.000

  • 52087 measured reflections

  • 14795 independent reflections

  • 12167 reflections with I > 2[sigma](I)

  • Rint = 0.032

Refinement
  • R[F2 > 2[sigma](F2)] = 0.042

  • wR(F2) = 0.116

  • S = 1.02

  • 14795 reflections

  • 1197 parameters

  • 12 restraints

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

  • [Delta][rho]max = 0.51 e Å-3

  • [Delta][rho]min = -0.29 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N6A-H6AA...O3Ei 0.85 (2) 2.06 (2) 2.8943 (18) 167.5 (18)
N6A-H6AB...O3Dii 0.91 (2) 2.08 (2) 2.8671 (18) 143.1 (16)
N6A-H6AB...O4Dii 0.91 (2) 2.25 (2) 2.961 (2) 134.6 (15)
N6A-H6AC...N4C 0.95 (2) 1.87 (2) 2.8157 (19) 172.5 (18)
N6B-H6BA...O3Biii 0.92 (2) 2.117 (19) 2.8728 (17) 138.5 (15)
N6B-H6BA...O4Biii 0.92 (2) 2.268 (19) 3.006 (2) 136.6 (15)
N6B-H6BB...O3B 0.89 (2) 2.00 (2) 2.8502 (17) 161.0 (19)
N6B-H6BC...N4Aiv 0.92 (2) 1.88 (2) 2.7988 (19) 173.4 (17)
N6C-H6CA...O2Cv 0.85 (2) 2.305 (18) 2.8334 (19) 120.9 (15)
N6C-H6CA...O3Cv 0.85 (2) 2.10 (2) 2.8944 (18) 155.4 (17)
N6C-H6CB...O3Avi 0.89 (2) 2.174 (19) 2.9145 (18) 140.2 (16)
N6C-H6CB...O4Avi 0.89 (2) 2.270 (19) 2.986 (2) 137.3 (15)
N6C-H6CC...N4Dvi 0.92 (2) 1.91 (2) 2.8179 (19) 167.6 (17)
N6D-H6DA...O2Avii 0.89 (2) 2.361 (19) 2.9631 (19) 124.9 (15)
N6D-H6DA...O3Avii 0.89 (2) 2.06 (2) 2.8340 (17) 145.0 (16)
N6D-H6DB...O3Cvi 0.89 (2) 2.16 (2) 2.9171 (17) 142.0 (17)
N6D-H6DB...O4Cvi 0.89 (2) 2.27 (2) 2.9323 (19) 130.5 (16)
N6D-H6DC...N4E 0.89 (2) 1.91 (2) 2.7932 (19) 174.0 (17)
N6E-H6EA...O2Dviii 0.91 (2) 2.32 (2) 2.973 (2) 128.7 (17)
N6E-H6EA...O3Dviii 0.91 (2) 2.06 (2) 2.8527 (18) 145.4 (18)
N6E-H6EB...O3E 0.87 (2) 2.19 (2) 2.9056 (18) 139.6 (17)
N6E-H6EB...O4E 0.87 (2) 2.33 (2) 3.010 (2) 135.3 (16)
N6E-H6EC...N4Bviii 0.93 (2) 1.85 (2) 2.7750 (19) 174.0 (19)
C8A-H8A...O2Bix 0.95 2.46 3.0887 (19) 123
C9A-H9A...O5E 0.95 2.43 3.243 (2) 144
C12A-H12B...O7Aix 0.99 2.46 3.313 (2) 145
C9B-H9B...O5Bi 0.95 2.37 3.224 (2) 150
C12B-H12D...O7Cvi 0.99 2.47 3.335 (2) 145
C8C-H8C...O5Cvi 0.95 2.33 3.194 (2) 152
C9C-H9C...O2Ei 0.95 2.49 3.105 (2) 123
C7D-H7D...O5Avi 0.95 2.35 3.233 (2) 155
C11D-H11H...O6Avi 0.99 2.55 3.421 (2) 147
C12D-H12G...O6Bvii 0.99 2.43 3.238 (2) 139
C9E-H9E...O5Dii 0.95 2.27 3.162 (6) 156
C9E-H9E...O5DAii 0.95 2.56 3.357 (17) 141
C12E-H12I...O6Eviii 0.99 2.34 3.186 (2) 142
Symmetry codes: (i) x+1, y, z; (ii) [x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]; (iii) -x+1, -y+1, -z; (iv) [-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (v) -x+2, -y+1, -z+1; (vi) -x+1, -y+1, -z+1; (vii) -x, -y+1, -z+1; (viii) [x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]; (ix) [-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: CrysAlis PRO (Agilent, 2012[Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Agilent, 2012[Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.]); program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007[Palatinus, L. & Chapuis, G. (2007). J. Appl. Cryst. 40, 786-790.]); program(s) used to refine structure: SHELXL2012 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: 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.]); software used to prepare material for publication: OLEX2.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SJ5352 ).


Acknowledgements

TSY thanks the UOM for research facilities and is also grateful to the Principal, Maharani's Science College for Women, Mysore, for giving permission to do research. JPJ acknowledges the NSF-MRI program (grant No. CHE-1039027) for funds to purchase the X-ray diffractometer.

References

Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans 2, pp. S1-19.
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Du, M. & Zhao, X.-J. (2003). Acta Cryst. E59, o1898-o1900.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Dutkiewicz, G., Samshuddin, S., Narayana, B., Yathirajan, H. S. & Kubicki, M. (2011). Acta Cryst. E67, o235.  [CSD] [CrossRef] [IUCr Journals]
In, Y., Nagata, H., Doi, M., Ishida, T. & Wakahara, A. (1997). Acta Cryst. C53, 367-369.  [CSD] [CrossRef] [IUCr Journals]
Jin, C. M., Ye, C., Piekarski, C., Twamley, B. & Shreeve, J. M. (2005). Eur. J. Inorg. Chem. pp. 3760-3767.  [Web of Science] [CSD] [CrossRef]
Krezel, I. (1998). Farmaco, 53, 342-345.  [CrossRef] [ChemPort] [PubMed]
Lombardino, J. G. & Wiseman, E. H. (1974). J. Med. Chem. 17, 1182-1188.  [CrossRef] [ChemPort] [PubMed] [Web of Science]
MacDonald, J., Yigit, M. V. & Mychajlonka, K. (2005). Cryst. Growth Des. 5, 2248-2255.  [CSD] [CrossRef] [ChemPort]
Maier, T., Schmierer, R., Bauer, K., Bieringer, H., Buerstell, H. & Sachse, B. (1989a). US Patent 4 820 335.
Maier, T., Schmierer, R., Bauer, K., Bieringer, H., Buerstell, H. & Sachse, B. (1989b). Chem. Abstr. 111, 19494.
Nardelli, M., Pelizzi, G., Vitali, F., Bordi, F., Plazzi, P. V. & Vitali, T. (1987). Acta Cryst. C43, 507-514.  [CSD] [CrossRef] [IUCr Journals]
Palatinus, L. & Chapuis, G. (2007). J. Appl. Cryst. 40, 786-790.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Pi, M., Liu, X.-L., Xu, J.-J. & Jin, C.-M. (2009). Acta Cryst. E65, o2386.  [CSD] [CrossRef] [IUCr Journals]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Soriano-García, M., Schatz-Levine, M., Toscano, R. A. & Villena Iribe, R. (1990). Acta Cryst. C46, 1556-1558.  [CSD] [CrossRef] [IUCr Journals]


Acta Cryst (2013). E69, o1572-o1573   [ doi:10.1107/S1600536813025646 ]

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