(2-Chloro-6-methyl­quinolin-3-yl)methanol

Abstract

The title compound, C₁₁H₁₀ClNO, is close to being planar (r.m.s deviation for the non-H atoms = 0.026 Å). In the crystal, mol­ecules are linked by O—H⋯O hydrogen bonds, generating C(2) chains, and weak C—H⋯π inter­actions and aromatic π–π stacking inter­actions [centroid–centroid distance = 3.713 (3) Å] help to consolidate the structure.

Related literature

For a related structure and background references, see: Roopan et al. (2010 ▶). For the structure of the starting material, see: Khan et al. (2009 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

• C₁₁H₁₀ClNO

• M _r = 207.65

• Monoclinic,

• a = 14.8091 (17) Å

• b = 4.6387 (5) Å

• c = 14.5098 (11) Å

• β = 96.594 (9)°

• V = 990.16 (17) ų

• Z = 4

• Mo Kα radiation

• μ = 0.35 mm⁻¹

• T = 295 K

• 0.35 × 0.15 × 0.08 mm

Data collection

• Oxford Xcalibur Eos(Nova) CCD diffractometer

• Absorption correction: multi-scan CrysAlis PRO RED (Oxford Diffraction, 2009 ▶) T _min = 0.888, T _max = 0.973

• 15485 measured reflections

• 1721 independent reflections

• 913 reflections with I > 2σ(I)

• R _int = 0.136

Refinement

• R[F ² > 2σ(F ²)] = 0.085

• wR(F ²) = 0.222

• S = 0.94

• 1721 reflections

• 131 parameters

• H atoms treated by a mixture of independent and constrained refinement

• Δρ_max = 0.41 e Å⁻³

• Δρ_min = −0.46 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 ▶).

Supplementary Material

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

Table 1. Hydrogen-bond geometry (Å, °).

Cg1 is the centroid of the N1/C1/C6–C9 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O⋯O1i	0.79 (6)	1.93 (6)	2.716 (5)	177 (7)
C10—H10A⋯Cg1ii	0.97	2.73	3.526 (5)	139

Symmetry codes: (i) ; (ii) .

supplementary crystallographic information

Comment

The importance and general background of the title compound is given in our earler paper (Roopan et al., 2010).

The molecule of the title compound, (I), (Fig. 1), except the hydroxyl and methyl H atoms, is close to planar (r.m.s deviation 0.026 Å).

An intramolecular C—H···O hydrogen bond generates an S(5) ring motif (Bernstein et al., 1995). Molecules of (I) are linked via O—H···O hydrogen bonds (Table 1, Fig. 2), an intermolecular C–H···π interactions between the aromatic H atoms of the ethenol substituent and the pyridine (N1/C1/C6–C9) ring of an adjacent molecule (Table 1), and π-π stacking interactions helping to stabilize the crystal structure [Cg1···Cg2(x, 1 + y, z) = 3.713 (3) Å, where Cg1 and Cg2 are centroids of the N1/C1/C6–C9 and C1–C6 rings, respectively].

Experimental

2-Chloro-6-methylquinoline-3-carbaldehyde (206 mg, 1 mmol), sodium borohydride (38 mg, 1 mmol) and catalytic amount of montmorillonite K-10 were taken in an open vessel and the resulting mixture was irradiating at 500 W for 5 min. Ethylacetate was poured into the reaction mixture and filtered off. The filtrated after removal of solvent was subjected to column chromatography packed with silica and ethyl acetate/petroleum ether was used as the eluant. Colourless plates of (I) were grown by solvent evaporation from a solution of the compound in chloroform.

Refinement

The H atom of the OH group were located in difference map and its positional parameters were refined freely [O1—H1O = 0.79 (6) Å]. The other H atoms were positioned geometrically, with C—H = 0.93–0.97 Å, and refined as riding with U_iso(H) = 1.2 or 1.5 U_eq(C). The value of R_int [0.136] is greater than 0.12. Since the overall quality of the data may be poor due to the crystal quality.

Figures

Fig. 1.

View of the molecular structure of (I), showing 50% probability displacement ellipsoids.

Fig. 2.

Molecular packing and the hydrogen bonding of (I) viewed down b axis. The H atoms not involved in hydrogen bonds have been omitted for clarity.

Crystal data

C11H10ClNO	F(000) = 432
Mr = 207.65	Dx = 1.393 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 865 reflections
a = 14.8091 (17) Å	θ = 2.7–21.4°
b = 4.6387 (5) Å	µ = 0.35 mm−1
c = 14.5098 (11) Å	T = 295 K
β = 96.594 (9)°	Plate, colourless
V = 990.16 (17) Å3	0.35 × 0.15 × 0.08 mm
Z = 4

Data collection

Oxford Xcalibur Eos(Nova) CCD diffractometer	1721 independent reflections
Radiation source: Enhance (Mo) X-ray Source	913 reflections with I > 2σ(I)
graphite	Rint = 0.136
ω scans	θmax = 25.0°, θmin = 3.0°
Absorption correction: multi-scan CrysAlis PRO RED (Oxford Diffraction, 2009)	h = −17→17
Tmin = 0.888, Tmax = 0.973	k = −5→5
15485 measured reflections	l = −17→17

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)] = 0.085	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.222	H atoms treated by a mixture of independent and constrained refinement
S = 0.94	w = 1/[σ2(Fo2) + (0.1359P)2] where P = (Fo2 + 2Fc2)/3
1721 reflections	(Δ/σ)max < 0.001
131 parameters	Δρmax = 0.41 e Å−3
0 restraints	Δρmin = −0.46 e Å−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Cl1	0.13152 (10)	0.6780 (3)	−0.04947 (8)	0.0717 (6)
O1	0.0334 (3)	0.9035 (7)	0.2189 (2)	0.0580 (14)
N1	0.2440 (3)	0.3573 (8)	0.0535 (2)	0.0448 (14)
C1	0.2832 (3)	0.2406 (10)	0.1357 (3)	0.0409 (16)
C2	0.3535 (3)	0.0442 (11)	0.1360 (3)	0.0554 (19)
C3	0.3939 (3)	−0.0710 (12)	0.2179 (4)	0.0583 (19)
C4	0.3645 (3)	0.0074 (11)	0.3034 (3)	0.0529 (19)
C5	0.2963 (3)	0.1980 (10)	0.3040 (3)	0.0454 (16)
C6	0.2534 (3)	0.3238 (9)	0.2222 (3)	0.0369 (16)
C7	0.1817 (3)	0.5231 (9)	0.2194 (3)	0.0438 (16)
C8	0.1412 (3)	0.6383 (9)	0.1376 (3)	0.0414 (16)
C9	0.1799 (3)	0.5394 (10)	0.0572 (3)	0.0454 (16)
C10	0.0641 (3)	0.8449 (9)	0.1312 (3)	0.0465 (17)
C11	0.4114 (4)	−0.1220 (14)	0.3929 (4)	0.078 (2)
H1O	0.014 (4)	0.756 (13)	0.235 (4)	0.0870*
H2	0.37380	−0.01050	0.08020	0.0670*
H3	0.44130	−0.20220	0.21680	0.0700*
H5	0.27670	0.24850	0.36050	0.0550*
H7	0.16080	0.57900	0.27480	0.0520*
H10A	0.08270	1.02420	0.10460	0.0560*
H10B	0.01400	0.76690	0.08970	0.0560*
H11A	0.37370	−0.09620	0.44180	0.1170*
H11B	0.46870	−0.02720	0.40930	0.1170*
H11C	0.42160	−0.32400	0.38410	0.1170*

Atomic displacement parameters (Ų)

	U11	U22	U33	U12	U13	U23
Cl1	0.0999 (12)	0.0913 (12)	0.0243 (7)	0.0084 (8)	0.0089 (6)	0.0093 (6)
O1	0.085 (3)	0.051 (2)	0.043 (2)	0.0031 (19)	0.0292 (17)	−0.0008 (17)
N1	0.066 (3)	0.048 (2)	0.0223 (19)	−0.001 (2)	0.0139 (17)	−0.0045 (16)
C1	0.048 (3)	0.051 (3)	0.025 (2)	−0.003 (2)	0.0102 (18)	−0.007 (2)
C2	0.061 (3)	0.073 (4)	0.035 (3)	−0.005 (3)	0.018 (2)	−0.007 (2)
C3	0.056 (3)	0.069 (4)	0.051 (3)	0.004 (3)	0.011 (2)	−0.009 (3)
C4	0.056 (3)	0.070 (4)	0.033 (3)	−0.001 (3)	0.007 (2)	0.006 (2)
C5	0.056 (3)	0.056 (3)	0.025 (2)	−0.005 (2)	0.008 (2)	−0.004 (2)
C6	0.050 (3)	0.041 (3)	0.021 (2)	−0.001 (2)	0.0102 (18)	−0.0049 (18)
C7	0.063 (3)	0.053 (3)	0.017 (2)	−0.009 (3)	0.0118 (19)	−0.0055 (19)
C8	0.056 (3)	0.042 (3)	0.028 (2)	−0.007 (2)	0.0125 (19)	−0.003 (2)
C9	0.068 (3)	0.049 (3)	0.020 (2)	−0.005 (3)	0.009 (2)	0.000 (2)
C10	0.070 (3)	0.037 (3)	0.035 (3)	−0.003 (2)	0.017 (2)	−0.003 (2)
C11	0.087 (4)	0.105 (5)	0.041 (3)	0.009 (3)	0.001 (3)	0.006 (3)

Geometric parameters (Å, °)

Cl1—C9	1.751 (5)	C7—C8	1.375 (6)
O1—C10	1.426 (5)	C8—C9	1.433 (6)
O1—H1O	0.79 (6)	C8—C10	1.485 (6)
N1—C9	1.276 (6)	C2—H2	0.9300
N1—C1	1.376 (5)	C3—H3	0.9300
C1—C2	1.383 (7)	C5—H5	0.9300
C1—C6	1.431 (6)	C7—H7	0.9300
C2—C3	1.376 (7)	C10—H10A	0.9700
C3—C4	1.409 (7)	C10—H10B	0.9700
C4—C11	1.524 (7)	C11—H11A	0.9600
C4—C5	1.343 (7)	C11—H11B	0.9600
C5—C6	1.407 (6)	C11—H11C	0.9600
C6—C7	1.405 (6)
C10—O1—H1O	105 (4)	O1—C10—C8	112.9 (4)
C1—N1—C9	117.8 (4)	C1—C2—H2	120.00
N1—C1—C2	120.3 (4)	C3—C2—H2	120.00
N1—C1—C6	120.8 (4)	C2—C3—H3	120.00
C2—C1—C6	118.9 (4)	C4—C3—H3	120.00
C1—C2—C3	120.7 (4)	C4—C5—H5	119.00
C2—C3—C4	120.8 (4)	C6—C5—H5	119.00
C3—C4—C11	119.5 (4)	C6—C7—H7	119.00
C5—C4—C11	121.6 (4)	C8—C7—H7	119.00
C3—C4—C5	119.0 (4)	O1—C10—H10A	109.00
C4—C5—C6	122.3 (4)	O1—C10—H10B	109.00
C1—C6—C5	118.3 (4)	C8—C10—H10A	109.00
C5—C6—C7	124.3 (4)	C8—C10—H10B	109.00
C1—C6—C7	117.4 (4)	H10A—C10—H10B	108.00
C6—C7—C8	122.3 (4)	C4—C11—H11A	110.00
C7—C8—C10	124.1 (4)	C4—C11—H11B	110.00
C9—C8—C10	122.2 (4)	C4—C11—H11C	110.00
C7—C8—C9	113.8 (4)	H11A—C11—H11B	109.00
Cl1—C9—N1	115.9 (3)	H11A—C11—H11C	110.00
N1—C9—C8	128.0 (4)	H11B—C11—H11C	109.00
Cl1—C9—C8	116.2 (3)
C9—N1—C1—C2	−179.4 (4)	C11—C4—C5—C6	178.8 (5)
C9—N1—C1—C6	−0.6 (7)	C4—C5—C6—C1	1.0 (7)
C1—N1—C9—Cl1	−179.3 (3)	C4—C5—C6—C7	179.8 (5)
C1—N1—C9—C8	−1.1 (7)	C1—C6—C7—C8	−0.5 (6)
N1—C1—C2—C3	179.2 (5)	C5—C6—C7—C8	−179.3 (4)
C6—C1—C2—C3	0.4 (7)	C6—C7—C8—C9	−0.9 (6)
N1—C1—C6—C5	−179.8 (4)	C6—C7—C8—C10	178.7 (4)
N1—C1—C6—C7	1.4 (6)	C7—C8—C9—Cl1	−180.0 (3)
C2—C1—C6—C5	−1.0 (6)	C7—C8—C9—N1	1.8 (7)
C2—C1—C6—C7	−179.8 (4)	C10—C8—C9—Cl1	0.4 (6)
C1—C2—C3—C4	0.2 (8)	C10—C8—C9—N1	−177.8 (4)
C2—C3—C4—C5	−0.2 (7)	C7—C8—C10—O1	−2.5 (6)
C2—C3—C4—C11	−179.4 (5)	C9—C8—C10—O1	177.1 (4)
C3—C4—C5—C6	−0.4 (7)

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the N1/C1/C6–C9 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···O1i	0.79 (6)	1.93 (6)	2.716 (5)	177 (7)
C10—H10A···Cg1ii	0.97	2.73	3.526 (5)	139

Symmetry codes: (i) −x, y−1/2, −z+1/2; (ii) x, y+1, z.