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Volume 69 
Part 1 
Page o82  
January 2013  

Received 23 November 2012
Accepted 30 November 2012
Online 15 December 2012

Key indicators
Single-crystal X-ray study
T = 295 K
Mean [sigma](C-C) = 0.011 Å
Disorder in main residue
R = 0.068
wR = 0.217
Data-to-parameter ratio = 22.8
Details
Open access

6-Ethoxycarbonyl-5,7-dihydroxy-2,3-dihydro-1H-pyrido[3,2,1-ij]quinolinium tribromide

aDepartment of Chemistry, Moscow State University, Moscow 119992, Russian Federation,bSTC `Institute for Single Crystals', National Academy of Sciences of Ukraine, 60 Lenina Avenue, Kharkiv 61001, Ukraine, and cNational University of Pharmacy, 4 Blyukhera Street, Kharkiv 61002, Ukraine
Correspondence e-mail: rybakov20021@yandex.ru

In the title salt, C15H16NO4+.Br3-, classical intramolecular O-H...O hydrogen bonds are found, which results in the co-planarity of the ester substituents with the quinolinium residue [C-C-C-O torsion angle = 1.0 (10)°]. The bromine anions are placed on both sides of heterocyclic cation and form Br...N contacts of 3.674 (9) and 3.860 (9) Å, which confirms the location of positive charge on the N atom. Non-classical intermolecular C-H...Br interactions stabilize the three-dimensional crystal structure. Moreover, anion...[pi] interactions are noted [Br...ring centroid range = 3.367 (9)-3.697 (9) Å]. The partly saturated heterocycle is disordered over two sofa conformations with occupancies in the ratio 0.56 (2):0.44 (2).

Related literature

For general background, see: Ukrainets et al. (2004[Ukrainets, I. V., Petrushova, L. A., Sidorenko, L. V., Rybakov, V. B. & Chernyshev, V. V. (2004). Zh. Org. Farm. Khim. 2, 26-31.], 2007[Ukrainets, I. V., Sidorenko, L. V. & Golovchenko, O. S. (2007). Chem. Heterocycl. Compd, pp. 1008-1013.]). For chemical bond lengths, see: Bürgi & Dunitz (1994[Bürgi, H.-B. & Dunitz, J. D. (1994). Structure Correlation, Vol. 2, pp. 767-784. Weinheim: VCH.]).

[Scheme 1]

Experimental

Crystal data
  • C15H16NO4+·Br3-

  • Mr = 513.99

  • Triclinic, [P \overline 1]

  • a = 7.6491 (8) Å

  • b = 9.1729 (10) Å

  • c = 13.3722 (14) Å

  • [alpha] = 102.355 (9)°

  • [beta] = 98.777 (9)°

  • [gamma] = 98.093 (9)°

  • V = 891.06 (17) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 6.81 mm-1

  • T = 295 K

  • 0.20 × 0.05 × 0.05 mm

Data collection
  • Agilent Xcalibur-3 CCD diffractometer

  • Absorption correction: multi-scan (CrysAlis RED; Agilent, 2011[Agilent (2011). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, Oxfordshire, England.]) Tmin = 0.343, Tmax = 0.727

  • 10147 measured reflections

  • 5106 independent reflections

  • 1855 reflections with I > 2[sigma](I)

  • Rint = 0.034

Refinement
  • R[F2 > 2[sigma](F2)] = 0.068

  • wR(F2) = 0.217

  • S = 0.90

  • 5106 reflections

  • 224 parameters

  • 5 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 1.02 e Å-3

  • [Delta][rho]min = -0.74 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O2-H2...O4 0.82 1.93 2.631 (7) 142
O1-H1...O3 0.82 1.73 2.459 (10) 147
C3-H3...Br1i 0.93 2.90 3.810 (9) 168
C4-H4...Br2ii 0.93 3.06 3.846 (9) 143
C10-H10B...Br2 0.97 2.99 3.936 (8) 166
C10-H10C...Br4iii 0.97 2.92 3.752 (8) 144
C11A-H11B...Br4iii 0.97 3.02 3.797 (17) 138
Symmetry codes: (i) x-1, y, z; (ii) x-1, y-1, z; (iii) -x, -y, -z.

Data collection: CrysAlis CCD (Agilent, 2011[Agilent (2011). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, Oxfordshire, England.]); cell refinement: CrysAlis RED (Agilent, 2011[Agilent (2011). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, Oxfordshire, England.]); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: AA2080 ).


References

Agilent (2011). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, Oxfordshire, England.
Bürgi, H.-B. & Dunitz, J. D. (1994). Structure Correlation, Vol. 2, pp. 767-784. Weinheim: VCH.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Ukrainets, I. V., Petrushova, L. A., Sidorenko, L. V., Rybakov, V. B. & Chernyshev, V. V. (2004). Zh. Org. Farm. Khim. 2, 26-31.  [ChemPort]
Ukrainets, I. V., Sidorenko, L. V. & Golovchenko, O. S. (2007). Chem. Heterocycl. Compd, pp. 1008-1013.


Acta Cryst (2013). E69, o82  [ doi:10.1107/S1600536812049276 ]

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