(2-Chloro-benzo[h]quinolin-3-yl)methanol.

In the title mol-ecule, C(14)H(10)ClNO, all non-H atoms are coplanar (r.m.s deviation = 0.0266 Å). In the crystal, symmetry-related mol-ecules are hydrogen bonded via inter-molecular O-H⋯O inter-actions, forming chains along the b axis.

Related literature

The title compound was obtained by the reduction of an aldehyde using Montmorillonite K-10 as catalyst. For background to the use of Montmorillonite clays as catalysts, see: Roopan et al. (2009b ▶). For related structures, see: Khan et al. (2010a ▶,b ▶); Roopan et al. (2009a ▶).

Experimental

Crystal data

C14H10ClNO

M = 243.68

Monoclinic,

a = 16.6953 (4) Å

b = 4.61459 (11) Å

c = 14.5588 (3) Å

β = 95.123 (2)°

V = 1117.16 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.32 mm−1

T = 295 K

0.35 × 0.30 × 0.28 mm

Data collection

Oxford Diffraction Xcalibur diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T min = 0.896, T max = 0.915

11643 measured reflections

2200 independent reflections

1717 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.093

S = 1.08

2200 reflections

155 parameters

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.22 e Å−3

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

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810010767/pv2269sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810010767/pv2269Isup2.hkl

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

C14H10ClNO	F(000) = 504
Mr = 243.68	Dx = 1.449 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 11643 reflections
a = 16.6953 (4) Å	θ = 2.5–26.0°
b = 4.61459 (11) Å	µ = 0.32 mm−1
c = 14.5588 (3) Å	T = 295 K
β = 95.123 (2)°	Block, colourless
V = 1117.16 (5) Å3	0.35 × 0.30 × 0.28 mm
Z = 4

Oxford Diffraction Xcalibur diffractometer	2200 independent reflections
Radiation source: fine-focus sealed tube	1717 reflections with I > 2σ(I)
graphite	Rint = 0.028
ω scans	θmax = 26.0°, θmin = 2.5°
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	h = −20→20
Tmin = 0.896, Tmax = 0.915	k = −5→5
11643 measured reflections	l = −17→17

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.093	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.0447P)2 + 0.1644P] where P = (Fo2 + 2Fc2)/3
2200 reflections	(Δ/σ)max = 0.001
155 parameters	Δρmax = 0.19 e Å−3
0 restraints	Δρmin = −0.22 e Å−3

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

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) 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	0.38036 (3)	0.30225 (12)	0.55246 (3)	0.05783 (19)
N1	0.28031 (8)	0.6236 (3)	0.45110 (8)	0.0350 (3)
O1	0.47139 (8)	0.0886 (3)	0.28368 (8)	0.0497 (3)
H1	0.4911	0.2355	0.2633	0.074*
C2	0.37487 (9)	0.3556 (3)	0.36689 (10)	0.0315 (3)
C1	0.33981 (9)	0.4434 (3)	0.44662 (10)	0.0331 (4)
C7	0.18191 (9)	0.9418 (4)	0.37325 (11)	0.0366 (4)
C9	0.27796 (9)	0.6741 (3)	0.28570 (10)	0.0333 (4)
C3	0.34176 (9)	0.4759 (3)	0.28642 (10)	0.0339 (4)
H3	0.3619	0.4254	0.2311	0.041*
C4	0.24384 (10)	0.8084 (4)	0.20323 (11)	0.0426 (4)
H4	0.2637	0.7635	0.1472	0.051*
C8	0.24801 (9)	0.7420 (3)	0.37074 (10)	0.0309 (3)
C6	0.14987 (10)	1.0709 (4)	0.28978 (12)	0.0417 (4)
C13	0.14771 (10)	1.0095 (4)	0.45516 (12)	0.0478 (4)
H13	0.1685	0.9266	0.5105	0.057*
C5	0.18321 (11)	0.9994 (4)	0.20550 (12)	0.0477 (5)
H5	0.1625	1.0872	0.1510	0.057*
C14	0.44481 (9)	0.1482 (4)	0.37137 (11)	0.0395 (4)
H14A	0.4891	0.2296	0.4108	0.047*
H14B	0.4291	−0.0321	0.3990	0.047*
C10	0.08499 (11)	1.2661 (4)	0.29225 (15)	0.0551 (5)
H10	0.0639	1.3552	0.2381	0.066*
C11	0.05304 (11)	1.3253 (5)	0.37239 (16)	0.0638 (6)
H11	0.0100	1.4531	0.3726	0.077*
C12	0.08390 (12)	1.1971 (5)	0.45434 (15)	0.0609 (6)
H12	0.0612	1.2386	0.5089	0.073*

	U11	U22	U33	U12	U13	U23
Cl1	0.0679 (3)	0.0734 (4)	0.0331 (2)	0.0227 (3)	0.0093 (2)	0.0130 (2)
N1	0.0384 (7)	0.0381 (8)	0.0294 (7)	0.0009 (6)	0.0085 (5)	−0.0015 (6)
O1	0.0613 (8)	0.0343 (7)	0.0590 (8)	0.0033 (6)	0.0365 (6)	−0.0016 (6)
C2	0.0339 (8)	0.0279 (8)	0.0340 (8)	−0.0049 (7)	0.0095 (6)	−0.0023 (6)
C1	0.0390 (8)	0.0338 (9)	0.0274 (8)	−0.0005 (7)	0.0076 (6)	0.0018 (7)
C7	0.0335 (8)	0.0339 (9)	0.0424 (9)	−0.0040 (7)	0.0040 (7)	−0.0054 (7)
C9	0.0355 (8)	0.0351 (9)	0.0297 (8)	−0.0068 (7)	0.0049 (6)	−0.0011 (7)
C3	0.0388 (8)	0.0368 (9)	0.0277 (8)	−0.0058 (7)	0.0122 (6)	−0.0062 (7)
C4	0.0469 (10)	0.0511 (11)	0.0299 (8)	−0.0052 (9)	0.0047 (7)	−0.0014 (8)
C8	0.0316 (8)	0.0321 (8)	0.0293 (7)	−0.0040 (6)	0.0051 (6)	−0.0030 (6)
C6	0.0380 (9)	0.0358 (9)	0.0500 (10)	−0.0046 (7)	−0.0034 (7)	−0.0026 (8)
C13	0.0440 (10)	0.0516 (11)	0.0484 (10)	0.0057 (9)	0.0075 (8)	−0.0106 (8)
C5	0.0511 (10)	0.0491 (11)	0.0410 (9)	−0.0024 (9)	−0.0062 (8)	0.0071 (8)
C14	0.0422 (9)	0.0354 (10)	0.0429 (9)	0.0008 (7)	0.0145 (7)	0.0001 (7)
C10	0.0465 (11)	0.0458 (11)	0.0697 (13)	0.0043 (9)	−0.0130 (9)	−0.0032 (10)
C11	0.0427 (11)	0.0594 (13)	0.0874 (16)	0.0163 (10)	−0.0053 (10)	−0.0185 (12)
C12	0.0467 (11)	0.0668 (14)	0.0698 (13)	0.0104 (10)	0.0094 (9)	−0.0210 (11)

Cl1—C1	1.7525 (15)	C4—C5	1.345 (2)
N1—C1	1.3014 (19)	C4—H4	0.9300
N1—C8	1.3585 (19)	C6—C10	1.412 (2)
O1—C14	1.4155 (19)	C6—C5	1.430 (2)
O1—H1	0.8200	C13—C12	1.372 (2)
C2—C3	1.368 (2)	C13—H13	0.9300
C2—C1	1.405 (2)	C5—H5	0.9300
C2—C14	1.507 (2)	C14—H14A	0.9700
C7—C13	1.402 (2)	C14—H14B	0.9700
C7—C6	1.415 (2)	C10—C11	1.353 (3)
C7—C8	1.441 (2)	C10—H10	0.9300
C9—C3	1.403 (2)	C11—C12	1.389 (3)
C9—C8	1.411 (2)	C11—H11	0.9300
C9—C4	1.424 (2)	C12—H12	0.9300
C3—H3	0.9300
C1—N1—C8	117.39 (13)	C10—C6—C5	121.83 (17)
C14—O1—H1	109.5	C7—C6—C5	119.57 (16)
C3—C2—C1	115.09 (14)	C12—C13—C7	120.52 (18)
C3—C2—C14	123.18 (14)	C12—C13—H13	119.7
C1—C2—C14	121.71 (14)	C7—C13—H13	119.7
N1—C1—C2	126.98 (14)	C4—C5—C6	121.58 (16)
N1—C1—Cl1	115.47 (11)	C4—C5—H5	119.2
C2—C1—Cl1	117.54 (12)	C6—C5—H5	119.2
C13—C7—C6	119.02 (16)	O1—C14—C2	112.85 (13)
C13—C7—C8	122.33 (15)	O1—C14—H14A	109.0
C6—C7—C8	118.64 (15)	C2—C14—H14A	109.0
C3—C9—C8	117.80 (13)	O1—C14—H14B	109.0
C3—C9—C4	122.41 (14)	C2—C14—H14B	109.0
C8—C9—C4	119.78 (15)	H14A—C14—H14B	107.8
C2—C3—C9	121.29 (14)	C11—C10—C6	120.88 (18)
C2—C3—H3	119.4	C11—C10—H10	119.6
C9—C3—H3	119.4	C6—C10—H10	119.6
C5—C4—C9	120.65 (16)	C10—C11—C12	120.66 (18)
C5—C4—H4	119.7	C10—C11—H11	119.7
C9—C4—H4	119.7	C12—C11—H11	119.7
N1—C8—C9	121.44 (14)	C13—C12—C11	120.30 (19)
N1—C8—C7	118.79 (13)	C13—C12—H12	119.8
C9—C8—C7	119.77 (13)	C11—C12—H12	119.8
C10—C6—C7	118.61 (17)
C8—N1—C1—C2	−0.2 (2)	C6—C7—C8—N1	178.27 (14)
C8—N1—C1—Cl1	178.89 (11)	C13—C7—C8—C9	177.63 (15)
C3—C2—C1—N1	0.1 (2)	C6—C7—C8—C9	−1.5 (2)
C14—C2—C1—N1	178.96 (15)	C13—C7—C6—C10	0.7 (2)
C3—C2—C1—Cl1	−178.97 (11)	C8—C7—C6—C10	179.84 (15)
C14—C2—C1—Cl1	−0.1 (2)	C13—C7—C6—C5	−178.81 (16)
C1—C2—C3—C9	0.6 (2)	C8—C7—C6—C5	0.4 (2)
C14—C2—C3—C9	−178.32 (14)	C6—C7—C13—C12	0.3 (3)
C8—C9—C3—C2	−1.0 (2)	C8—C7—C13—C12	−178.85 (16)
C4—C9—C3—C2	178.28 (15)	C9—C4—C5—C6	−1.2 (3)
C3—C9—C4—C5	−179.35 (15)	C10—C6—C5—C4	−178.47 (16)
C8—C9—C4—C5	0.0 (2)	C7—C6—C5—C4	1.0 (3)
C1—N1—C8—C9	−0.4 (2)	C3—C2—C14—O1	−0.9 (2)
C1—N1—C8—C7	179.86 (14)	C1—C2—C14—O1	−179.73 (13)
C3—C9—C8—N1	0.9 (2)	C7—C6—C10—C11	−1.1 (3)
C4—C9—C8—N1	−178.40 (14)	C5—C6—C10—C11	178.35 (18)
C3—C9—C8—C7	−179.28 (13)	C6—C10—C11—C12	0.6 (3)
C4—C9—C8—C7	1.4 (2)	C7—C13—C12—C11	−0.8 (3)
C13—C7—C8—N1	−2.6 (2)	C10—C11—C12—C13	0.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O1i	0.82	1.90	2.7154 (12)	175
C3—H3···O1	0.93	2.47	2.809 (2)	102

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O1i	0.82	1.90	2.7154 (12)	175

Symmetry code: (i) .