(2-Chloro-8-meth-oxy-quinolin-3-yl)methanol monohydrate.

In the title compound, C(11)H(10)ClNO(2)·H(2)O, the organic mol-ecule is roughly planar (r.m.s. deviation = 0.074 Å). In the crystal structure, molecues are linked by O-H⋯O and O-H⋯N hydrogen bonds and weak C-H⋯π and π-π inter-actions [centroid-centroid distance = 3.578 (3) Å] consolidate the packing. A short Cl⋯O contact [3.147 (3) Å] is also observed.

Related literature

For further information on the starting material, see: Subashini et al. (2009 ▶). For general background to the title compound, see: Roopan et al. (2009 ▶). For related structures, see: Khan et al. (2010a ▶,b ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C11H10ClNO2·H2O

M = 241.67

Monoclinic,

a = 9.161 (5) Å

b = 14.246 (5) Å

c = 9.464 (5) Å

β = 116.819 (5)°

V = 1102.3 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.34 mm−1

T = 290 K

0.31 × 0.21 × 0.10 mm

Data collection

Oxford Xcalibur Eos (Nova) CCD detector diffractometer

Absorption correction: multi-scan (CrysAlis PRO RED; Oxford Diffraction, 2009 ▶) T min = 0.903, T max = 0.967

8360 measured reflections

2044 independent reflections

1212 reflections with I > 2σ(I)

R int = 0.100

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.134

S = 0.90

2044 reflections

153 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.40 e Å−3

Δρmin = −0.26 e Å−3

Data collection: CrysAlis PRO CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis PRO CCD; data reduction: CrysAlis PRO RED (Oxford Diffraction, 2009 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810020489/hb5469sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810020489/hb5469Isup2.hkl

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

C11H10ClNO2·H2O	F(000) = 504
Mr = 241.67	Dx = 1.456 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1021 reflections
a = 9.161 (5) Å	θ = 1.9–20.2°
b = 14.246 (5) Å	µ = 0.34 mm−1
c = 9.464 (5) Å	T = 290 K
β = 116.819 (5)°	Slab, colourless
V = 1102.3 (9) Å3	0.31 × 0.21 × 0.10 mm
Z = 4

Oxford Xcalibur Eos (Nova) CCD detector diffractometer	2044 independent reflections
Radiation source: Enhance (Mo) X-ray Source	1212 reflections with I > 2σ(I)
graphite	Rint = 0.100
ω scans	θmax = 25.5°, θmin = 2.9°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −11→11
Tmin = 0.903, Tmax = 0.967	k = −17→17
8360 measured reflections	l = −11→11

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.134	H atoms treated by a mixture of independent and constrained refinement
S = 0.90	w = 1/[σ2(Fo2) + (0.0692P)2] where P = (Fo2 + 2Fc2)/3
2044 reflections	(Δ/σ)max < 0.001
153 parameters	Δρmax = 0.40 e Å−3
0 restraints	Δρmin = −0.26 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
Cl1	−0.12994 (10)	0.21700 (5)	−0.05478 (9)	0.0525 (3)
O1	0.0858 (3)	0.2656 (2)	−0.3822 (3)	0.0713 (10)
O2	0.1487 (3)	0.46372 (14)	0.3536 (2)	0.0515 (8)
N1	0.0521 (3)	0.35801 (15)	0.0948 (3)	0.0371 (8)
C1	0.0114 (4)	0.30580 (19)	−0.0297 (3)	0.0399 (10)
C2	0.0664 (4)	0.3140 (2)	−0.1453 (3)	0.0435 (10)
C3	0.1715 (4)	0.3870 (2)	−0.1243 (3)	0.0493 (11)
C4	0.3261 (4)	0.5254 (2)	0.0313 (4)	0.0558 (12)
C5	0.3720 (4)	0.5792 (2)	0.1620 (5)	0.0603 (14)
C6	0.3158 (4)	0.5601 (2)	0.2743 (4)	0.0545 (12)
C7	0.2105 (4)	0.4875 (2)	0.2525 (3)	0.0436 (10)
C8	0.1595 (3)	0.43029 (18)	0.1160 (3)	0.0379 (9)
C9	0.2198 (4)	0.4484 (2)	0.0056 (3)	0.0444 (11)
C10	0.0147 (4)	0.2459 (3)	−0.2813 (4)	0.0573 (11)
C11	0.2035 (5)	0.5135 (3)	0.4973 (4)	0.0678 (16)
O3	0.8868 (3)	0.3074 (2)	0.2937 (3)	0.0716 (10)
H1O	0.18120	0.24780	−0.34070	0.1070*
H3	0.21180	0.39630	−0.19750	0.0590*
H4	0.36470	0.53900	−0.04200	0.0670*
H5	0.44190	0.62970	0.17760	0.0730*
H6	0.35070	0.59720	0.36460	0.0660*
H10A	0.04510	0.18290	−0.23950	0.0690*
H10B	−0.10340	0.24780	−0.34210	0.0690*
H11A	0.32050	0.50900	0.55460	0.1020*
H11B	0.15520	0.48700	0.55960	0.1020*
H11C	0.17230	0.57820	0.47550	0.1020*
H1W	0.943 (5)	0.331 (3)	0.252 (5)	0.1080*
H2W	0.949 (6)	0.301 (3)	0.389 (5)	0.1080*

	U11	U22	U33	U12	U13	U23
Cl1	0.0537 (5)	0.0487 (5)	0.0489 (5)	−0.0099 (4)	0.0176 (4)	−0.0054 (4)
O1	0.0644 (17)	0.112 (2)	0.0369 (13)	0.0262 (15)	0.0223 (13)	0.0030 (12)
O2	0.0555 (15)	0.0550 (14)	0.0428 (12)	−0.0026 (11)	0.0212 (11)	−0.0056 (10)
N1	0.0369 (14)	0.0372 (14)	0.0321 (13)	0.0029 (11)	0.0112 (11)	0.0046 (11)
C1	0.0379 (17)	0.0400 (17)	0.0342 (17)	0.0072 (14)	0.0096 (14)	0.0066 (13)
C2	0.0369 (17)	0.054 (2)	0.0324 (17)	0.0087 (15)	0.0094 (14)	0.0063 (13)
C3	0.047 (2)	0.067 (2)	0.0379 (18)	0.0167 (18)	0.0228 (16)	0.0161 (16)
C4	0.042 (2)	0.056 (2)	0.072 (2)	0.0051 (17)	0.0280 (18)	0.0169 (19)
C5	0.043 (2)	0.040 (2)	0.090 (3)	−0.0063 (16)	0.023 (2)	0.0051 (19)
C6	0.047 (2)	0.044 (2)	0.061 (2)	−0.0025 (16)	0.0141 (18)	−0.0045 (16)
C7	0.0358 (17)	0.0434 (18)	0.0448 (19)	0.0081 (15)	0.0122 (15)	0.0033 (14)
C8	0.0317 (16)	0.0343 (16)	0.0396 (16)	0.0055 (14)	0.0089 (14)	0.0054 (13)
C9	0.0380 (18)	0.0480 (19)	0.0458 (19)	0.0053 (15)	0.0176 (16)	0.0110 (15)
C10	0.056 (2)	0.076 (2)	0.0358 (19)	0.0121 (18)	0.0170 (17)	−0.0025 (16)
C11	0.071 (3)	0.078 (3)	0.046 (2)	0.000 (2)	0.019 (2)	−0.0121 (17)
O3	0.0575 (17)	0.108 (2)	0.0480 (15)	−0.0196 (15)	0.0226 (13)	0.0007 (15)

Cl1—C1	1.748 (4)	C4—C9	1.413 (5)
O1—C10	1.406 (5)	C5—C6	1.401 (6)
O2—C7	1.356 (4)	C6—C7	1.365 (5)
O2—C11	1.410 (4)	C7—C8	1.417 (4)
O1—H1O	0.8200	C8—C9	1.409 (4)
O3—H1W	0.85 (5)	C3—H3	0.9300
O3—H2W	0.83 (4)	C4—H4	0.9300
N1—C1	1.298 (4)	C5—H5	0.9300
N1—C8	1.375 (4)	C6—H6	0.9300
C1—C2	1.401 (5)	C10—H10B	0.9700
C2—C3	1.369 (5)	C10—H10A	0.9700
C2—C10	1.507 (5)	C11—H11C	0.9600
C3—C9	1.408 (4)	C11—H11A	0.9600
C4—C5	1.351 (5)	C11—H11B	0.9600
Cl1···O2i	3.147 (3)
C7—O2—C11	118.3 (3)	C3—C9—C8	117.4 (3)
C10—O1—H1O	109.00	O1—C10—C2	112.8 (3)
H1W—O3—H2W	107 (5)	C2—C3—H3	119.00
C1—N1—C8	117.1 (3)	C9—C3—H3	119.00
Cl1—C1—N1	115.5 (3)	C5—C4—H4	120.00
Cl1—C1—C2	117.4 (2)	C9—C4—H4	120.00
N1—C1—C2	127.2 (3)	C6—C5—H5	120.00
C1—C2—C10	121.9 (3)	C4—C5—H5	119.00
C1—C2—C3	115.3 (3)	C7—C6—H6	120.00
C3—C2—C10	122.8 (3)	C5—C6—H6	120.00
C2—C3—C9	121.5 (3)	O1—C10—H10A	109.00
C5—C4—C9	120.2 (3)	C2—C10—H10A	109.00
C4—C5—C6	121.0 (3)	C2—C10—H10B	109.00
C5—C6—C7	120.6 (3)	O1—C10—H10B	109.00
O2—C7—C8	115.4 (3)	H10A—C10—H10B	108.00
C6—C7—C8	119.6 (3)	O2—C11—H11B	109.00
O2—C7—C6	125.0 (3)	O2—C11—H11C	110.00
N1—C8—C9	121.6 (2)	O2—C11—H11A	109.00
N1—C8—C7	118.9 (3)	H11A—C11—H11C	109.00
C7—C8—C9	119.5 (3)	H11B—C11—H11C	110.00
C3—C9—C4	123.6 (3)	H11A—C11—H11B	109.00
C4—C9—C8	119.0 (3)
C11—O2—C7—C6	−4.0 (5)	C2—C3—C9—C8	1.8 (5)
C11—O2—C7—C8	175.5 (3)	C9—C4—C5—C6	0.0 (6)
C8—N1—C1—Cl1	−178.2 (2)	C5—C4—C9—C3	−177.5 (3)
C8—N1—C1—C2	0.8 (5)	C5—C4—C9—C8	1.6 (5)
C1—N1—C8—C7	−178.4 (3)	C4—C5—C6—C7	−1.3 (6)
C1—N1—C8—C9	1.5 (4)	C5—C6—C7—O2	−179.7 (3)
Cl1—C1—C2—C3	177.3 (2)	C5—C6—C7—C8	0.9 (5)
Cl1—C1—C2—C10	−3.6 (4)	O2—C7—C8—N1	1.1 (4)
N1—C1—C2—C3	−1.7 (5)	O2—C7—C8—C9	−178.8 (3)
N1—C1—C2—C10	177.4 (3)	C6—C7—C8—N1	−179.3 (3)
C1—C2—C3—C9	0.3 (5)	C6—C7—C8—C9	0.8 (5)
C10—C2—C3—C9	−178.8 (3)	N1—C8—C9—C3	−2.7 (4)
C1—C2—C10—O1	−179.0 (3)	N1—C8—C9—C4	178.1 (3)
C3—C2—C10—O1	0.1 (5)	C7—C8—C9—C3	177.1 (3)
C2—C3—C9—C4	−179.1 (3)	C7—C8—C9—C4	−2.0 (4)

Cg1 is the centroid of the N1/C1–C3/C8/C9 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···O3i	0.82	1.90	2.705 (4)	165
O3—H1W···N1ii	0.85 (5)	2.17 (5)	2.988 (4)	163 (4)
O3—H2W···O1iii	0.83 (4)	2.02 (4)	2.836 (4)	171 (5)
C10—H10B···Cg1i	0.97	2.93	3.738 (5)	142

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the N1/C1–C3/C8/C9 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O⋯O3i	0.82	1.90	2.705 (4)	165
O3—H1W⋯N1ii	0.85 (5)	2.17 (5)	2.988 (4)	163 (4)
O3—H2W⋯O1iii	0.83 (4)	2.02 (4)	2.836 (4)	171 (5)
C10—H10B⋯Cg1i	0.97	2.93	3.738 (5)	142

Symmetry codes: (i) ; (ii) ; (iii) .