5,7-Dichloro­quinolin-8-ol

Ng, S.W.

doi:10.1107/S1600536809014846

organic compounds

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ISSN: 2056-9890

Volume 65| Part 5| May 2009| Page o1131

doi:10.1107/S1600536809014846

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5,7-Dichloroquinolin-8-ol

Seik Weng Ng ^a ^*

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

(Received 20 April 2009; accepted 21 April 2009; online 25 April 2009)

The molecule of the title compound, C₉H₅Cl₂NO, is essentially planar [give maximum or r.m.s. deviation] and the hydroxy group acts as a hydrogen-bond donor to the N atom of a symmetry-related molecule, generating a hydrogen-bonded dimer,which lies on a twofold rotation axis.

Related literature

Unlike quinolin-8-ol, which yields a large number of metal derivatives, 5,7-dichloroquinolin-8-ol forms only a small number of metal chelates. For their crystal structures, see: García-Granda et al. (1987 ); Artizzu et al. (2007 , 2008 ); Day et al. (1980 ); González-Baró et al. (1998 ); Horton & Wendlandt (1963 ); Miyashita et al. (2005 ); Suganuma et al. (2001 ); Van Deun et al. (2004 ).

Experimental

Crystal data

C₉H₅Cl₂NO
M_r = 214.04
Monoclinic, P 2/c
a = 15.5726 (3) Å
b = 3.8062 (1) Å
c = 16.1269 (3) Å
β = 118.029 (1)°
V = 843.76 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.72 mm⁻¹
T = 123 K
0.36 × 0.09 × 0.02 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.782, T_max = 0.986
7279 measured reflections
1919 independent reflections
1644 reflections with I > 2σ(I)
R_int = 0.032

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.112
S = 1.05
1919 reflections
122 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.55 e Å⁻³
Δρ_min = −0.36 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1ⁱ	0.84 (1)	2.01 (2)	2.761 (2)	150 (3)
Symmetry code: (i) $[-x, y, -z+{\script{1\over 2}}]$ .

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/S1600536809014846/lh2808sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809014846/lh2808Isup2.hkl

checkCIF report

Comment top

A hydrogen-bonded dimer of the title compound is shown in Fig. 1.

Related literature top

Unlike quinolin-8-ol, which yields a large number of metal derivatives, 5,7-dichloroquinolin-8-ol forms only a small number of metal chelates. For their crystal structures, see: García-Granda et al. (1987); Artizzu et al. (2007, 2008); Day et al. (1980); González-Baró et al. (1998); Horton & Wendlandt (1963); Miyashita et al. (2005); Suganuma et al. (2001); Van Deun et al. (2004).

Experimental top

The organic reactant was returned unchanged in an unsuccessful attempt at reacting it with a zinc salt in methanol.

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 hydrogen-bonded dimer of the title compound; ellipsoids are drawn at the 70% probability level and H atoms of arbitrary radius. The unlabeled molecule is related by the symmetry operator -x, y, -z+1/2

5,7-Dichloroquinolin-8-ol top

Crystal data top

C₉H₅Cl₂NO	F(000) = 432
M_r = 214.04	D_x = 1.685 Mg m⁻³
Monoclinic, P2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yc	Cell parameters from 3573 reflections
a = 15.5726 (3) Å	θ = 2.5–28.3°
b = 3.8062 (1) Å	µ = 0.72 mm⁻¹
c = 16.1269 (3) Å	T = 123 K
β = 118.029 (1)°	Plate, colorless
V = 843.76 (3) Å³	0.36 × 0.09 × 0.02 mm
Z = 4

Data collection top

Bruker SMART APEX diffractometer	1919 independent reflections
Radiation source: fine-focus sealed tube	1644 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.032
ω scans	θ_max = 27.5°, θ_min = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −20→20
T_min = 0.782, T_max = 0.986	k = −4→4
7279 measured reflections	l = −20→20

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.112	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0684P)² + 0.4949P] where P = (F_o² + 2F_c²)/3
1919 reflections	(Δ/σ)_max < 0.001
122 parameters	Δρ_max = 0.55 e Å⁻³
1 restraint	Δρ_min = −0.36 e Å⁻³

Crystal data top

C₉H₅Cl₂NO	V = 843.76 (3) Å³
M_r = 214.04	Z = 4
Monoclinic, P2/c	Mo Kα radiation
a = 15.5726 (3) Å	µ = 0.72 mm⁻¹
b = 3.8062 (1) Å	T = 123 K
c = 16.1269 (3) Å	0.36 × 0.09 × 0.02 mm
β = 118.029 (1)°

Data collection top

Bruker SMART APEX diffractometer	1919 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1644 reflections with I > 2σ(I)
T_min = 0.782, T_max = 0.986	R_int = 0.032
7279 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	1 restraint
wR(F²) = 0.112	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.55 e Å⁻³
1919 reflections	Δρ_min = −0.36 e Å⁻³
122 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

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

	x	y	z	U_iso*/U_eq
Cl1	0.29367 (4)	0.38966 (13)	0.24587 (3)	0.02310 (17)
Cl2	0.44255 (4)	0.89258 (14)	0.59720 (3)	0.02635 (18)
O1	0.10638 (11)	0.6233 (4)	0.22642 (10)	0.0223 (3)
N1	0.07459 (12)	0.9357 (4)	0.36439 (11)	0.0186 (4)
H1	0.0565 (14)	0.729 (7)	0.220 (2)	0.051 (9)*
C1	0.18119 (14)	0.6852 (5)	0.31223 (13)	0.0176 (4)
C2	0.27416 (15)	0.5885 (5)	0.33230 (13)	0.0184 (4)
C3	0.35486 (14)	0.6504 (5)	0.42003 (14)	0.0193 (4)
H3	0.4180	0.5794	0.4316	0.023*
C4	0.34192 (14)	0.8134 (5)	0.48869 (13)	0.0183 (4)
C5	0.24865 (14)	0.9212 (5)	0.47354 (13)	0.0168 (4)
C6	0.16747 (14)	0.8502 (5)	0.38470 (13)	0.0170 (4)
C7	0.23008 (15)	1.0924 (5)	0.54108 (13)	0.0191 (4)
H7	0.2822	1.1462	0.6013	0.023*
C8	0.13659 (15)	1.1807 (5)	0.51946 (14)	0.0201 (4)
H8	0.1230	1.2970	0.5641	0.024*
C9	0.06103 (15)	1.0957 (5)	0.42978 (14)	0.0204 (4)
H9	−0.0036	1.1574	0.4155	0.024*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0336 (3)	0.0238 (3)	0.0188 (3)	0.00576 (19)	0.0180 (2)	0.00172 (18)
Cl2	0.0229 (3)	0.0305 (3)	0.0203 (3)	0.0002 (2)	0.0057 (2)	−0.00406 (19)
O1	0.0229 (7)	0.0304 (8)	0.0137 (6)	0.0030 (6)	0.0086 (6)	−0.0021 (5)
N1	0.0230 (8)	0.0202 (9)	0.0157 (7)	0.0008 (6)	0.0117 (6)	0.0020 (6)
C1	0.0242 (10)	0.0166 (9)	0.0139 (8)	−0.0012 (7)	0.0105 (7)	0.0016 (7)
C2	0.0280 (10)	0.0158 (10)	0.0171 (9)	0.0009 (7)	0.0154 (8)	0.0016 (7)
C3	0.0223 (9)	0.0173 (10)	0.0215 (9)	0.0015 (7)	0.0130 (8)	0.0025 (8)
C4	0.0211 (9)	0.0182 (10)	0.0145 (8)	−0.0019 (7)	0.0074 (7)	0.0014 (7)
C5	0.0216 (9)	0.0142 (9)	0.0164 (9)	−0.0012 (7)	0.0104 (7)	0.0021 (7)
C6	0.0220 (9)	0.0161 (9)	0.0162 (9)	−0.0010 (7)	0.0117 (7)	0.0010 (7)
C7	0.0276 (10)	0.0183 (10)	0.0143 (8)	−0.0029 (8)	0.0122 (8)	−0.0001 (7)
C8	0.0297 (10)	0.0187 (10)	0.0181 (9)	−0.0013 (8)	0.0164 (8)	−0.0007 (7)
C9	0.0263 (10)	0.0210 (10)	0.0200 (9)	0.0004 (8)	0.0160 (8)	0.0019 (7)

Geometric parameters (Å, º) top

Cl1—C2	1.7337 (19)	C3—H3	0.9500
Cl2—C4	1.7412 (19)	C4—C5	1.416 (3)
O1—C1	1.346 (2)	C5—C7	1.411 (3)
O1—H1	0.835 (10)	C5—C6	1.422 (3)
N1—C9	1.318 (2)	C7—C8	1.370 (3)
N1—C6	1.364 (2)	C7—H7	0.9500
C1—C2	1.377 (3)	C8—C9	1.408 (3)
C1—C6	1.428 (3)	C8—H8	0.9500
C2—C3	1.402 (3)	C9—H9	0.9500
C3—C4	1.364 (3)

C1—O1—H1	111 (2)	C7—C5—C6	117.26 (17)
C9—N1—C6	117.95 (17)	C4—C5—C6	118.24 (17)
O1—C1—C2	120.07 (17)	N1—C6—C5	122.49 (17)
O1—C1—C6	121.87 (17)	N1—C6—C1	117.25 (17)
C2—C1—C6	118.05 (17)	C5—C6—C1	120.26 (17)
C1—C2—C3	122.49 (18)	C8—C7—C5	119.71 (18)
C1—C2—Cl1	119.33 (15)	C8—C7—H7	120.1
C3—C2—Cl1	118.17 (15)	C5—C7—H7	120.1
C4—C3—C2	119.43 (18)	C7—C8—C9	118.71 (17)
C4—C3—H3	120.3	C7—C8—H8	120.6
C2—C3—H3	120.3	C9—C8—H8	120.6
C3—C4—C5	121.50 (18)	N1—C9—C8	123.88 (18)
C3—C4—Cl2	119.21 (15)	N1—C9—H9	118.1
C5—C4—Cl2	119.28 (14)	C8—C9—H9	118.1
C7—C5—C4	124.50 (18)

O1—C1—C2—C3	179.21 (17)	C7—C5—C6—N1	−1.1 (3)
C6—C1—C2—C3	−0.9 (3)	C4—C5—C6—N1	178.25 (17)
O1—C1—C2—Cl1	0.4 (3)	C7—C5—C6—C1	178.50 (17)
C6—C1—C2—Cl1	−179.66 (14)	C4—C5—C6—C1	−2.1 (3)
C1—C2—C3—C4	−0.2 (3)	O1—C1—C6—N1	1.6 (3)
Cl1—C2—C3—C4	178.56 (15)	C2—C1—C6—N1	−178.29 (17)
C2—C3—C4—C5	0.2 (3)	O1—C1—C6—C5	−178.02 (17)
C2—C3—C4—Cl2	−179.52 (14)	C2—C1—C6—C5	2.1 (3)
C3—C4—C5—C7	−179.67 (18)	C4—C5—C7—C8	−179.00 (19)
Cl2—C4—C5—C7	0.0 (3)	C6—C5—C7—C8	0.3 (3)
C3—C4—C5—C6	1.0 (3)	C5—C7—C8—C9	0.3 (3)
Cl2—C4—C5—C6	−179.31 (14)	C6—N1—C9—C8	−0.6 (3)
C9—N1—C6—C5	1.2 (3)	C7—C8—C9—N1	−0.2 (3)
C9—N1—C6—C1	−178.39 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1ⁱ	0.84 (1)	2.01 (2)	2.761 (2)	150 (3)

Symmetry code: (i) −x, y, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₉H₅Cl₂NO
M_r	214.04
Crystal system, space group	Monoclinic, P2/c
Temperature (K)	123
a, b, c (Å)	15.5726 (3), 3.8062 (1), 16.1269 (3)
β (°)	118.029 (1)
V (Å³)	843.76 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.72
Crystal size (mm)	0.36 × 0.09 × 0.02

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.782, 0.986
No. of measured, independent and observed [I > 2σ(I)] reflections	7279, 1919, 1644
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.112, 1.05
No. of reflections	1919
No. of parameters	122
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.55, −0.36

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—H1···N1ⁱ	0.84 (1)	2.01 (2)	2.761 (2)	150 (3)

Symmetry code: (i) −x, y, −z+1/2.

Acknowledgements

I thank the University of Malaya for supporting this study.

References

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