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Acta Crystallogr Sect E Struct Rep Online. 2009 June 1; 65(Pt 6): o1450.
Published online 2009 May 29. doi:  10.1107/S160053680901993X
PMCID: PMC2969641

5-Chloro-8-hydroxy­quinolinium nitrate

Abstract

The 5-chloro-8-hydroxy­quinolinium cation in the the title ion pair, C9H7ClNO+·NO3 , is approximately coplanar with the nitrate anion [dihedral angle = 16.1 (1)°]. Two ion pairs are hydrogen bonded (2 × O—H(...)O and 2 × N—H(...)O) about a center of inversion, generating an R 4 4(14) ring.

Related literature

The 8-hydroxy­quinolinium cation has been isolated as a number of salts; for the 8-hydroxy­quinolinium chloride hydrate, see: Skakle et al. (2006 [triangle]). For the crystal structure of 5-chloro-8-hydroxy­quinoline, see: Banerjee & Saha (1986 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-o1450-scheme1.jpg

Experimental

Crystal data

  • C9H7ClNO+·NO3
  • M r = 242.62
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o1450-efi1.jpg
  • a = 7.4379 (3) Å
  • b = 11.5518 (6) Å
  • c = 11.2288 (5) Å
  • β = 95.831 (3)°
  • V = 959.80 (8) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.40 mm−1
  • T = 123 K
  • 0.20 × 0.05 × 0.05 mm

Data collection

  • Bruker SMART APEX diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.925, T max = 0.980
  • 6472 measured reflections
  • 2196 independent reflections
  • 1574 reflections with I > 2˘I)
  • R int = 0.049

Refinement

  • R[F 2 > 2σ(F 2)] = 0.062
  • wR(F 2) = 0.192
  • S = 1.07
  • 2196 reflections
  • 153 parameters
  • 2 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 1.20 e Å−3
  • Δρmin = −0.34 e Å−3

Data collection: APEX2 (Bruker, 2008 [triangle]); cell refinement: SAINT (Bruker, 2008 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2009 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680901993X/tk2465sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680901993X/tk2465Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

I thank the University of Malaya for supporting this study.

supplementary crystallographic information

Experimental

Zinc acetate (0.19 g, 1 mmol) and 5-chloro-8-hydroxyquinoline (0.36 g, 2 mmol) were loaded into a convection tube; the tube was filled with dry methanol and kept at 333 K. Yellow crystals were collected from the side-arm after several days.

Refinement

Carbon-bound H-atoms were placed in calculated positions (C–H 0.95 Å) and were included in the refinement in the riding model approximation with U(H) fixed at 1.2U(C). The ammonium and hydroxy H-atoms were located in a difference Fourier map, and were refined with distance restraints of N–H = 0.88±0.01 Å and O–H = 0.84±0.01 Å; their isotropic temperature factors were refined.

The final difference Fourier map had a large peak at about 1 Å from the Cl1 atom.

Figures

Fig. 1.
Thermal ellipsoid plot (Barbour, 2001) of a pair of hydrogen-bonded [C9H7ClNO][NO3] ion pairs drawn at the 70% probability level. Hydrogen atoms are drawn spheres of arbitrary radius and dashed lines denote hydrogen bonds.

Crystal data

C9H7ClNO+·NO3F(000) = 496
Mr = 242.62Dx = 1.679 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 1079 reflections
a = 7.4379 (3) Åθ = 2.5–26.4°
b = 11.5518 (6) ŵ = 0.40 mm1
c = 11.2288 (5) ÅT = 123 K
β = 95.831 (3)°Prism, yellow
V = 959.80 (8) Å30.20 × 0.05 × 0.05 mm
Z = 4

Data collection

Bruker SMART APEX diffractometer2196 independent reflections
Radiation source: fine-focus sealed tube1574 reflections with I > 2˘I)
graphiteRint = 0.049
ω scansθmax = 27.5°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −9→9
Tmin = 0.925, Tmax = 0.980k = −15→12
6472 measured reflectionsl = −14→14

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.062Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.192H atoms treated by a mixture of independent and constrained refinement
S = 1.07w = 1/[σ2(Fo2) + (0.1164P)2 + 0.1797P] where P = (Fo2 + 2Fc2)/3
2196 reflections(Δ/σ)max = 0.001
153 parametersΔρmax = 1.20 e Å3
2 restraintsΔρmin = −0.34 e Å3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
Cl1−0.30656 (11)0.30338 (8)0.76985 (8)0.0321 (3)
O10.3429 (3)0.4706 (2)0.5632 (2)0.0279 (6)
H1O0.350 (6)0.5423 (11)0.553 (4)0.042 (12)*
O20.5861 (3)0.30211 (18)0.4592 (2)0.0261 (6)
O30.6434 (3)0.12125 (19)0.4947 (2)0.0325 (6)
O40.8190 (3)0.2201 (2)0.3904 (2)0.0286 (6)
N10.2829 (4)0.2424 (2)0.5774 (2)0.0203 (6)
H1N0.385 (3)0.265 (4)0.552 (3)0.037 (11)*
N20.6849 (4)0.2125 (2)0.4472 (2)0.0220 (6)
C10.2635 (4)0.1291 (3)0.5806 (3)0.0250 (7)
H1A0.35160.08060.55040.030*
C20.1155 (5)0.0794 (3)0.6278 (3)0.0277 (7)
H20.1012−0.00230.62950.033*
C3−0.0094 (4)0.1513 (3)0.6720 (3)0.0265 (7)
H3−0.10930.11850.70630.032*
C40.0084 (4)0.2727 (3)0.6672 (3)0.0213 (7)
C5−0.1144 (4)0.3518 (3)0.7089 (3)0.0254 (7)
C6−0.0849 (5)0.4687 (3)0.7003 (3)0.0325 (8)
H6−0.16940.52130.72820.039*
C70.0666 (5)0.5118 (3)0.6513 (3)0.0297 (8)
H70.08320.59310.64600.036*
C80.1920 (4)0.4385 (3)0.6108 (3)0.0231 (7)
C90.1613 (4)0.3178 (3)0.6184 (3)0.0204 (7)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl10.0219 (5)0.0405 (6)0.0359 (5)−0.0012 (3)0.0128 (3)−0.0003 (4)
O10.0275 (13)0.0173 (12)0.0413 (14)0.0001 (9)0.0147 (10)0.0025 (10)
O20.0276 (13)0.0138 (11)0.0388 (13)0.0032 (9)0.0124 (10)−0.0010 (9)
O30.0337 (14)0.0145 (11)0.0513 (16)−0.0003 (9)0.0135 (12)0.0044 (10)
O40.0270 (13)0.0265 (13)0.0342 (13)0.0027 (9)0.0121 (10)−0.0009 (10)
N10.0173 (14)0.0205 (13)0.0235 (14)0.0010 (10)0.0046 (11)0.0003 (10)
N20.0214 (14)0.0175 (13)0.0274 (14)0.0005 (10)0.0038 (11)−0.0025 (10)
C10.0241 (17)0.0199 (16)0.0320 (18)0.0020 (12)0.0073 (13)−0.0003 (13)
C20.0278 (17)0.0205 (16)0.0356 (18)−0.0003 (13)0.0066 (14)0.0058 (14)
C30.0227 (17)0.0272 (17)0.0300 (17)−0.0079 (13)0.0043 (13)0.0027 (13)
C40.0208 (16)0.0253 (16)0.0180 (15)−0.0034 (12)0.0034 (12)0.0000 (12)
C50.0182 (16)0.0337 (19)0.0252 (16)−0.0003 (13)0.0074 (12)0.0025 (13)
C60.0271 (18)0.0279 (18)0.045 (2)0.0074 (14)0.0137 (15)−0.0051 (15)
C70.0291 (19)0.0210 (17)0.0405 (19)0.0021 (13)0.0111 (15)−0.0024 (14)
C80.0240 (16)0.0201 (16)0.0258 (16)−0.0012 (12)0.0058 (12)0.0006 (12)
C90.0239 (17)0.0171 (15)0.0203 (15)0.0021 (12)0.0021 (12)0.0009 (11)

Geometric parameters (Å, °)

Cl1—C51.739 (3)C2—H20.9500
O1—C81.343 (4)C3—C41.410 (5)
O1—H1O0.84 (1)C3—H30.9500
O2—N21.285 (3)C4—C51.405 (4)
O3—N21.234 (3)C4—C91.411 (4)
O4—N21.240 (4)C5—C61.374 (5)
N1—C11.318 (4)C6—C71.395 (5)
N1—C91.368 (4)C6—H60.9500
N1—H1N0.88 (1)C7—C81.371 (4)
C1—C21.393 (5)C7—H70.9500
C1—H1A0.9500C8—C91.417 (4)
C2—C31.375 (5)
C8—O1—H1O113 (3)C5—C4—C3124.6 (3)
C1—N1—C9123.0 (3)C9—C4—C3117.7 (3)
C1—N1—H1N114 (3)C6—C5—C4120.1 (3)
C9—N1—H1N123 (3)C6—C5—Cl1119.2 (3)
O3—N2—O4122.1 (3)C4—C5—Cl1120.7 (3)
O3—N2—O2118.2 (3)C5—C6—C7121.3 (3)
O4—N2—O2119.7 (3)C5—C6—H6119.3
N1—C1—C2120.8 (3)C7—C6—H6119.3
N1—C1—H1A119.6C8—C7—C6120.9 (3)
C2—C1—H1A119.6C8—C7—H7119.5
C3—C2—C1118.5 (3)C6—C7—H7119.5
C3—C2—H2120.7O1—C8—C7125.8 (3)
C1—C2—H2120.7O1—C8—C9116.3 (3)
C2—C3—C4121.2 (3)C7—C8—C9118.0 (3)
C2—C3—H3119.4N1—C9—C4118.8 (3)
C4—C3—H3119.4N1—C9—C8119.3 (3)
C5—C4—C9117.8 (3)C4—C9—C8121.9 (3)
C9—N1—C1—C2−0.5 (5)C6—C7—C8—O1−179.4 (3)
N1—C1—C2—C3−0.5 (5)C6—C7—C8—C91.0 (5)
C1—C2—C3—C41.6 (5)C1—N1—C9—C40.5 (4)
C2—C3—C4—C5179.2 (3)C1—N1—C9—C8−179.6 (3)
C2—C3—C4—C9−1.7 (5)C5—C4—C9—N1179.8 (3)
C9—C4—C5—C60.8 (5)C3—C4—C9—N10.6 (4)
C3—C4—C5—C6179.9 (3)C5—C4—C9—C8−0.2 (4)
C9—C4—C5—Cl1179.8 (2)C3—C4—C9—C8−179.4 (3)
C3—C4—C5—Cl1−1.1 (5)O1—C8—C9—N1−0.4 (4)
C4—C5—C6—C7−0.6 (5)C7—C8—C9—N1179.3 (3)
Cl1—C5—C6—C7−179.5 (3)O1—C8—C9—C4179.6 (3)
C5—C6—C7—C8−0.4 (6)C7—C8—C9—C4−0.7 (5)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1—H1o···O2i0.84 (1)1.87 (1)2.695 (3)169 (4)
N1—H1n···O20.88 (1)1.95 (1)2.816 (3)167 (4)

Symmetry codes: (i) −x+1, −y+1, −z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK2465).

References

  • Banerjee, T. & Saha, N. N. (1986). Acta Cryst. C42, 1408–1411.
  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  • Bruker (2008). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Skakle, J. M. S., Wardell, J. L. & Wardell, S. M. S. V. (2006). Acta Cryst. C62, o312–o314. [PubMed]
  • Westrip, S. P. (2009). publCIF In preparation.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography