5-Chloro-8-hydroxy­quinolinium nitrate

Ng, S.W.

doi:10.1107/S160053680901993X

organic compounds

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Volume 65| Part 6| June 2009| Page o1450

doi:10.1107/S160053680901993X

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5-Chloro-8-hydroxyquinolinium nitrate

Seik Weng Ng ^a ^*

^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 ). For the crystal structure of 5-chloro-8-hydroxyquinoline, see: Banerjee & Saha (1986 ).

Experimental

Crystal data

C₉H₇ClNO⁺·NO₃⁻
M_r = 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 ) 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[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
Δρ_max = 1.20 e Å⁻³
Δρ_min = −0.34 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	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 ); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; 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 ).

Supporting information

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

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

checkCIF report

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.

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

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⁺·NO₃⁻	F(000) = 496
M_r = 242.62	D_x = 1.679 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1079 reflections
a = 7.4379 (3) Å	θ = 2.5–26.4°
b = 11.5518 (6) Å	µ = 0.40 mm⁻¹
c = 11.2288 (5) Å	T = 123 K
β = 95.831 (3)°	Prism, yellow
V = 959.80 (8) Å³	0.20 × 0.05 × 0.05 mm
Z = 4

Data collection top

Bruker SMART APEX diffractometer	2196 independent reflections
Radiation source: fine-focus sealed tube	1574 reflections with I > 2˘I)
Graphite monochromator	R_int = 0.049
ω scans	θ_max = 27.5°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
T_min = 0.925, T_max = 0.980	k = −15→12
6472 measured reflections	l = −14→14

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.192	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ²(F_o²) + (0.1164P)² + 0.1797P] where P = (F_o² + 2F_c²)/3
2196 reflections	(Δ/σ)_max = 0.001
153 parameters	Δρ_max = 1.20 e Å⁻³
2 restraints	Δρ_min = −0.34 e Å⁻³

Crystal data top

C₉H₇ClNO⁺·NO₃⁻	V = 959.80 (8) Å³
M_r = 242.62	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 7.4379 (3) Å	µ = 0.40 mm⁻¹
b = 11.5518 (6) Å	T = 123 K
c = 11.2288 (5) Å	0.20 × 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)
T_min = 0.925, T_max = 0.980	R_int = 0.049
6472 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.062	2 restraints
wR(F²) = 0.192	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	Δρ_max = 1.20 e Å⁻³
2196 reflections	Δρ_min = −0.34 e Å⁻³
153 parameters

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

	x	y	z	U_iso*/U_eq
Cl1	−0.30656 (11)	0.30338 (8)	0.76985 (8)	0.0321 (3)
O1	0.3429 (3)	0.4706 (2)	0.5632 (2)	0.0279 (6)
H1O	0.350 (6)	0.5423 (11)	0.553 (4)	0.042 (12)*
O2	0.5861 (3)	0.30211 (18)	0.4592 (2)	0.0261 (6)
O3	0.6434 (3)	0.12125 (19)	0.4947 (2)	0.0325 (6)
O4	0.8190 (3)	0.2201 (2)	0.3904 (2)	0.0286 (6)
N1	0.2829 (4)	0.2424 (2)	0.5774 (2)	0.0203 (6)
H1N	0.385 (3)	0.265 (4)	0.552 (3)	0.037 (11)*
N2	0.6849 (4)	0.2125 (2)	0.4472 (2)	0.0220 (6)
C1	0.2635 (4)	0.1291 (3)	0.5806 (3)	0.0250 (7)
H1A	0.3516	0.0806	0.5504	0.030*
C2	0.1155 (5)	0.0794 (3)	0.6278 (3)	0.0277 (7)
H2	0.1012	−0.0023	0.6295	0.033*
C3	−0.0094 (4)	0.1513 (3)	0.6720 (3)	0.0265 (7)
H3	−0.1093	0.1185	0.7063	0.032*
C4	0.0084 (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	−0.1694	0.5213	0.7282	0.039*
C7	0.0666 (5)	0.5118 (3)	0.6513 (3)	0.0297 (8)
H7	0.0832	0.5931	0.6460	0.036*
C8	0.1920 (4)	0.4385 (3)	0.6108 (3)	0.0231 (7)
C9	0.1613 (4)	0.3178 (3)	0.6184 (3)	0.0204 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0219 (5)	0.0405 (6)	0.0359 (5)	−0.0012 (3)	0.0128 (3)	−0.0003 (4)
O1	0.0275 (13)	0.0173 (12)	0.0413 (14)	0.0001 (9)	0.0147 (10)	0.0025 (10)
O2	0.0276 (13)	0.0138 (11)	0.0388 (13)	0.0032 (9)	0.0124 (10)	−0.0010 (9)
O3	0.0337 (14)	0.0145 (11)	0.0513 (16)	−0.0003 (9)	0.0135 (12)	0.0044 (10)
O4	0.0270 (13)	0.0265 (13)	0.0342 (13)	0.0027 (9)	0.0121 (10)	−0.0009 (10)
N1	0.0173 (14)	0.0205 (13)	0.0235 (14)	0.0010 (10)	0.0046 (11)	0.0003 (10)
N2	0.0214 (14)	0.0175 (13)	0.0274 (14)	0.0005 (10)	0.0038 (11)	−0.0025 (10)
C1	0.0241 (17)	0.0199 (16)	0.0320 (18)	0.0020 (12)	0.0073 (13)	−0.0003 (13)
C2	0.0278 (17)	0.0205 (16)	0.0356 (18)	−0.0003 (13)	0.0066 (14)	0.0058 (14)
C3	0.0227 (17)	0.0272 (17)	0.0300 (17)	−0.0079 (13)	0.0043 (13)	0.0027 (13)
C4	0.0208 (16)	0.0253 (16)	0.0180 (15)	−0.0034 (12)	0.0034 (12)	0.0000 (12)
C5	0.0182 (16)	0.0337 (19)	0.0252 (16)	−0.0003 (13)	0.0074 (12)	0.0025 (13)
C6	0.0271 (18)	0.0279 (18)	0.045 (2)	0.0074 (14)	0.0137 (15)	−0.0051 (15)
C7	0.0291 (19)	0.0210 (17)	0.0405 (19)	0.0021 (13)	0.0111 (15)	−0.0024 (14)
C8	0.0240 (16)	0.0201 (16)	0.0258 (16)	−0.0012 (12)	0.0058 (12)	0.0006 (12)
C9	0.0239 (17)	0.0171 (15)	0.0203 (15)	0.0021 (12)	0.0021 (12)	0.0009 (11)

Geometric parameters (Å, º) top

Cl1—C5	1.739 (3)	C2—H2	0.9500
O1—C8	1.343 (4)	C3—C4	1.410 (5)
O1—H1O	0.84 (1)	C3—H3	0.9500
O2—N2	1.285 (3)	C4—C5	1.405 (4)
O3—N2	1.234 (3)	C4—C9	1.411 (4)
O4—N2	1.240 (4)	C5—C6	1.374 (5)
N1—C1	1.318 (4)	C6—C7	1.395 (5)
N1—C9	1.368 (4)	C6—H6	0.9500
N1—H1N	0.88 (1)	C7—C8	1.371 (4)
C1—C2	1.393 (5)	C7—H7	0.9500
C1—H1A	0.9500	C8—C9	1.417 (4)
C2—C3	1.375 (5)

C8—O1—H1O	113 (3)	C5—C4—C3	124.6 (3)
C1—N1—C9	123.0 (3)	C9—C4—C3	117.7 (3)
C1—N1—H1N	114 (3)	C6—C5—C4	120.1 (3)
C9—N1—H1N	123 (3)	C6—C5—Cl1	119.2 (3)
O3—N2—O4	122.1 (3)	C4—C5—Cl1	120.7 (3)
O3—N2—O2	118.2 (3)	C5—C6—C7	121.3 (3)
O4—N2—O2	119.7 (3)	C5—C6—H6	119.3
N1—C1—C2	120.8 (3)	C7—C6—H6	119.3
N1—C1—H1A	119.6	C8—C7—C6	120.9 (3)
C2—C1—H1A	119.6	C8—C7—H7	119.5
C3—C2—C1	118.5 (3)	C6—C7—H7	119.5
C3—C2—H2	120.7	O1—C8—C7	125.8 (3)
C1—C2—H2	120.7	O1—C8—C9	116.3 (3)
C2—C3—C4	121.2 (3)	C7—C8—C9	118.0 (3)
C2—C3—H3	119.4	N1—C9—C4	118.8 (3)
C4—C3—H3	119.4	N1—C9—C8	119.3 (3)
C5—C4—C9	117.8 (3)	C4—C9—C8	121.9 (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—C9	1.0 (5)
C1—C2—C3—C4	1.6 (5)	C1—N1—C9—C4	0.5 (4)
C2—C3—C4—C5	179.2 (3)	C1—N1—C9—C8	−179.6 (3)
C2—C3—C4—C9	−1.7 (5)	C5—C4—C9—N1	179.8 (3)
C9—C4—C5—C6	0.8 (5)	C3—C4—C9—N1	0.6 (4)
C3—C4—C5—C6	179.9 (3)	C5—C4—C9—C8	−0.2 (4)
C9—C4—C5—Cl1	179.8 (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—N1	179.3 (3)
Cl1—C5—C6—C7	−179.5 (3)	O1—C8—C9—C4	179.6 (3)
C5—C6—C7—C8	−0.4 (6)	C7—C8—C9—C4	−0.7 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	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.

Experimental details

Crystal data
Chemical formula	C₉H₇ClNO⁺·NO₃⁻
M_r	242.62
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	123
a, b, c (Å)	7.4379 (3), 11.5518 (6), 11.2288 (5)
β (°)	95.831 (3)
V (Å³)	959.80 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.40
Crystal size (mm)	0.20 × 0.05 × 0.05

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.925, 0.980
No. of measured, independent and observed [I > 2˘I)] reflections	6472, 2196, 1574
R_int	0.049
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.062, 0.192, 1.07
No. of reflections	2196
No. of parameters	153
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	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···A	D—H	H···A	D···A	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.

Acknowledgements

I thank the University of Malaya for supporting this study.

References

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