Abstract
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,
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[F 2 > 2σ(F 2)] = 0.040
wR(F 2) = 0.112
S = 1.05
1919 reflections
122 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρmax = 0.55 e Å−3
Δρmin = −0.36 e Å−3
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 ▶).
Supplementary Material
Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809014846/lh2808sup1.cif
Structure factors: contains datablocks I. DOI: 10.1107/S1600536809014846/lh2808Isup2.hkl
Additional supplementary materials: crystallographic information; 3D view; checkCIF report
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) 
.
Acknowledgments
I thank the University of Malaya for supporting this study.
supplementary crystallographic information
Comment
A hydrogen-bonded dimer of the title compound is shown in Fig. 1.
Experimental
The organic reactant was returned unchanged in an unsuccessful attempt at reacting it with a zinc salt in methanol.
Refinement
Carbon-bound H-atoms were placed in calculated positions (C–H 0.93 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2 U(C). The hydroxy hydrogen atom was located in a difference Fourier map, and was refined with a distance restraint of O–H 0.84±0.01 Å; its temperature factor was freely refined.
Figures
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
Crystal data
| C9H5Cl2NO | F(000) = 432 |
| Mr = 214.04 | Dx = 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
| Bruker SMART APEX diffractometer | 1919 independent reflections |
| Radiation source: fine-focus sealed tube | 1644 reflections with I > 2σ(I) |
| graphite | Rint = 0.032 |
| ω scans | θmax = 27.5°, θmin = 1.5° |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −20→20 |
| Tmin = 0.782, Tmax = 0.986 | k = −4→4 |
| 7279 measured reflections | l = −20→20 |
Refinement
| 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(Fo2) + (0.0684P)2 + 0.4949P] where P = (Fo2 + 2Fc2)/3 |
| 1919 reflections | (Δ/σ)max < 0.001 |
| 122 parameters | Δρmax = 0.55 e Å−3 |
| 1 restraint | Δρmin = −0.36 e Å−3 |
Special details
| 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)
| x | y | z | Uiso*/Ueq | ||
| 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)
| 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, °)
| 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, °)
| 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 codes: (i) −x, y, −z+1/2.
Footnotes
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH2808).
References
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Associated Data
This section collects any data citations, data availability statements, or supplementary materials included in this article.
Supplementary Materials
Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809014846/lh2808sup1.cif
Structure factors: contains datablocks I. DOI: 10.1107/S1600536809014846/lh2808Isup2.hkl
Additional supplementary materials: crystallographic information; 3D view; checkCIF report