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

Khan, F.N.; Roopan, S.M.; Kushwaha, A.K.; Hathwar, V.R.; Akkurt, M.

doi:10.1107/S1600536810020507

organic compounds

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Volume 66| Part 7| July 2010| Page o1544

doi:10.1107/S1600536810020507

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

F. Nawaz Khan,^a S. Mohana Roopan,^a Atul Kumar Kushwaha,^a Venkatesha R. Hathwar ^b and Mehmet Akkurt ^c ^*

^aOrganic and Medicinal Chemistry Research Laboratory, Organic Chemistry Division, School of Advanced Sciences, VIT University, Vellore 632 014, Tamil Nadu, India, ^bSolid State and Structural Chemistry Unit, Indian Institute of Science, Bangalore 560 012, Karnataka, India, and ^cDepartment of Physics, Faculty of Arts and Sciences, Erciyes University, 38039 Kayseri, Turkey
^*Correspondence e-mail: akkurt@erciyes.edu.tr

(Received 25 May 2010; accepted 29 May 2010; online 5 June 2010)

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, P 2₁ /c
a = 14.8091 (17) Å
b = 4.6387 (5) Å
c = 14.5098 (11) Å
β = 96.594 (9)°
V = 990.16 (17) Å³
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 $[Oxford Diffraction (2009). CrysAlis PRO CCD and CrysAlis PRO RED. Oxford Diffraction Ltd, Yarnton, England.]$ ) 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[F² > 2σ(F²)] = 0.085
wR(F²) = 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

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) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) x, y+1, z.

Data collection: CrysAlis PRO CCD (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO CCD and CrysAlis PRO RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis PRO CCD; data reduction: CrysAlis PRO RED (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO CCD and CrysAlis PRO RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); 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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810020507/hb5471sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810020507/hb5471Isup2.hkl

checkCIF report

Comment top

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].

Related literature top

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 top

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.

Computing details top

Data collection: CrysAlis PRO CCD (Oxford Diffraction, 2009); cell refinement: CrysAlis PRO CCD (Oxford Diffraction, 2009); 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).

Figures top

	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.

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

Crystal data top

C₁₁H₁₀ClNO	F(000) = 432
M_r = 207.65	D_x = 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 top

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

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)] = 0.085	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(F_o²) + (0.1359P)²] where P = (F_o² + 2F_c²)/3
1721 reflections	(Δ/σ)_max < 0.001
131 parameters	Δρ_max = 0.41 e Å⁻³
0 restraints	Δρ_min = −0.46 e Å⁻³

Crystal data top

C₁₁H₁₀ClNO	V = 990.16 (17) Å³
M_r = 207.65	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 14.8091 (17) Å	µ = 0.35 mm⁻¹
b = 4.6387 (5) Å	T = 295 K
c = 14.5098 (11) Å	0.35 × 0.15 × 0.08 mm
β = 96.594 (9)°

Data collection top

Oxford Xcalibur Eos(Nova) CCD diffractometer	1721 independent reflections
Absorption correction: multi-scan CrysAlis PRO RED (Oxford Diffraction, 2009)	913 reflections with I > 2σ(I)
T_min = 0.888, T_max = 0.973	R_int = 0.136
15485 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.085	0 restraints
wR(F²) = 0.222	H atoms treated by a mixture of independent and constrained refinement
S = 0.94	Δρ_max = 0.41 e Å⁻³
1721 reflections	Δρ_min = −0.46 e Å⁻³
131 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
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 (Å²) top

	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, º) top

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, º) top

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.

Experimental details

Crystal data
Chemical formula	C₁₁H₁₀ClNO
M_r	207.65
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	295
a, b, c (Å)	14.8091 (17), 4.6387 (5), 14.5098 (11)
β (°)	96.594 (9)
V (Å³)	990.16 (17)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.35
Crystal size (mm)	0.35 × 0.15 × 0.08

Data collection
Diffractometer	Oxford Xcalibur Eos(Nova) CCD diffractometer
Absorption correction	Multi-scan CrysAlis PRO RED (Oxford Diffraction, 2009)
T_min, T_max	0.888, 0.973
No. of measured, independent and observed [I > 2σ(I)] reflections	15485, 1721, 913
R_int	0.136
(sin θ/λ)_max (Å⁻¹)	0.594

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.085, 0.222, 0.94
No. of reflections	1721
No. of parameters	131
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.41, −0.46

Computer programs: CrysAlis PRO CCD (Oxford Diffraction, 2009), CrysAlis PRO RED (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

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.

Acknowledgements

We thank the Department of Science and Technology, India, for use of the CCD facility set up under the FIST–DST program at SSCU, IISc. We also thank Professor T. N. Guru Row, IISc, Bangalore, for his help with the data collection. FNK thanks the DST for Fast Track Proposal funding.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Khan, F. N., Subashini, R., Roopan, S. M., Hathwar, V. R. & Ng, S. W. (2009). Acta Cryst. E65, o2686. Web of Science CrossRef IUCr Journals Google Scholar
Oxford Diffraction (2009). CrysAlis PRO CCD and CrysAlis PRO RED. Oxford Diffraction Ltd, Yarnton, England. Google Scholar
Roopan, S. M., Khan, F. N., Kumar, A. S., Hathwar, V. R. & Akkurt, M. (2010). Acta Cryst. E66, o1542. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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doi:10.1107/S1600536810020507

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