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5-Chloro-8-hy­droxy­quinolinium nitrate

aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: seikweng@um.edu.my

(Received 25 May 2009; accepted 26 May 2009; online 29 May 2009)

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 R44(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[Skakle, J. M. S., Wardell, J. L. & Wardell, S. M. S. V. (2006). Acta Cryst. C62, o312-o314.]). For the crystal structure of 5-chloro-8-hydroxy­quinoline, see: Banerjee & Saha (1986[Banerjee, T. & Saha, N. N. (1986). Acta Cryst. C42, 1408-1411.]).

[Scheme 1]

Experimental

Crystal data
  • C9H7ClNO+·NO3

  • Mr = 242.62

  • Monoclinic, P 21 /n

  • 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[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.925, Tmax = 0.980

  • 6472 measured reflections

  • 2196 independent reflections

  • 1574 reflections with I > 2˘I)

  • Rint = 0.049

Refinement
  • R[F2 > 2σ(F2)] = 0.062

  • wR(F2) = 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

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O1—H1o⋯O2i 0.84 (1) 1.87 (1) 2.695 (3) 169 (4)
N1—H1n⋯O2 0.88 (1) 1.95 (1) 2.816 (3) 167 (4)
Symmetry code: (i) -x+1, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2 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: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]); software used to prepare material for publication: publCIF (Westrip, 2009[Westrip, S. P. (2009). publCIF. In preparation.]).

Supporting information


Related literature top

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

Experimental top

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 top

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.

Computing details top

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

Figures top
[Figure 1] 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.
5-Chloro-8-hydroxyquinolinium nitrate top
Crystal data top
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 top
Bruker SMART APEX
diffractometer
2196 independent reflections
Radiation source: fine-focus sealed tube1574 reflections with I > 2˘I)
Graphite monochromatorRint = 0.049
ω scansθmax = 27.5°, θmin = 2.5°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 99
Tmin = 0.925, Tmax = 0.980k = 1512
6472 measured reflectionsl = 1414
Refinement top
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 = 1.07 w = 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
Crystal data top
C9H7ClNO+·NO3V = 959.80 (8) Å3
Mr = 242.62Z = 4
Monoclinic, P21/nMo Kα radiation
a = 7.4379 (3) ŵ = 0.40 mm1
b = 11.5518 (6) ÅT = 123 K
c = 11.2288 (5) Å0.20 × 0.05 × 0.05 mm
β = 95.831 (3)°
Data collection top
Bruker SMART APEX
diffractometer
2196 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
1574 reflections with I > 2˘I)
Tmin = 0.925, Tmax = 0.980Rint = 0.049
6472 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0622 restraints
wR(F2) = 0.192H atoms treated by a mixture of independent and constrained refinement
S = 1.07Δρmax = 1.20 e Å3
2196 reflectionsΔρmin = 0.34 e Å3
153 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl10.30656 (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)
H20.10120.00230.62950.033*
C30.0094 (4)0.1513 (3)0.6720 (3)0.0265 (7)
H30.10930.11850.70630.032*
C40.0084 (4)0.2727 (3)0.6672 (3)0.0213 (7)
C50.1144 (4)0.3518 (3)0.7089 (3)0.0254 (7)
C60.0849 (5)0.4687 (3)0.7003 (3)0.0325 (8)
H60.16940.52130.72820.039*
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) top
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, º) top
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—C20.5 (5)C6—C7—C8—O1179.4 (3)
N1—C1—C2—C30.5 (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—C8179.6 (3)
C2—C3—C4—C91.7 (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—C80.2 (4)
C9—C4—C5—Cl1179.8 (2)C3—C4—C9—C8179.4 (3)
C3—C4—C5—Cl11.1 (5)O1—C8—C9—N10.4 (4)
C4—C5—C6—C70.6 (5)C7—C8—C9—N1179.3 (3)
Cl1—C5—C6—C7179.5 (3)O1—C8—C9—C4179.6 (3)
C5—C6—C7—C80.4 (6)C7—C8—C9—C40.7 (5)
Hydrogen-bond geometry (Å, º) top
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 code: (i) x+1, y+1, z+1.

Experimental details

Crystal data
Chemical formulaC9H7ClNO+·NO3
Mr242.62
Crystal system, space groupMonoclinic, P21/n
Temperature (K)123
a, b, c (Å)7.4379 (3), 11.5518 (6), 11.2288 (5)
β (°) 95.831 (3)
V3)959.80 (8)
Z4
Radiation typeMo Kα
µ (mm1)0.40
Crystal size (mm)0.20 × 0.05 × 0.05
Data collection
DiffractometerBruker SMART APEX
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.925, 0.980
No. of measured, independent and
observed [I > 2˘I)] reflections
6472, 2196, 1574
Rint0.049
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.062, 0.192, 1.07
No. of reflections2196
No. of parameters153
No. of restraints2
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)1.20, 0.34

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2009).

Hydrogen-bond geometry (Å, º) top
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 code: (i) x+1, y+1, z+1.
 

Acknowledgements

I thank the University of Malaya for supporting this study.

References

First citationBanerjee, T. & Saha, N. N. (1986). Acta Cryst. C42, 1408–1411.  CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
First citationBarbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.  CrossRef CAS Google Scholar
First citationBruker (2008). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSkakle, J. M. S., Wardell, J. L. & Wardell, S. M. S. V. (2006). Acta Cryst. C62, o312–o314.  Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
First citationWestrip, S. P. (2009). publCIF. In preparation.  Google Scholar

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