(2-Chloro-8-methyl­quinolin-3-yl)methanol

Roopan, S.M.; Khan, F.N.; Kumar, R.; Hathwar, V.R.; Akkurt, M.

doi:10.1107/S1600536810020490

organic compounds

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ISSN: 2056-9890

Volume 66| Part 7| July 2010| Page o1543

doi:10.1107/S1600536810020490

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(2-Chloro-8-methylquinolin-3-yl)methanol

S. Mohana Roopan,^a F. Nawaz Khan,^a Rajesh Kumar,^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 molecule of title compound, C₁₁H₁₀ClNO, is close to being planar (r.m.s deviation for the non-H atoms = 0.017 Å). In the crystal, molecules interact by way of O—H⋯O hydrogen bonds, generating C(2) chains propagating in [010]. The crystal structure is consolidated by C—H⋯π interactions and aromatic π–π stacking interactions [centroid–centroid distance = 3.661 (2) Å].

Related literature

For a related structure and background references, see: Roopan et al. (2010 ). For a similar structure, see: Khan et al. (2009 ).

Experimental

Crystal data

C₁₁H₁₀ClNO
M_r = 207.65
Monoclinic, P 2₁ /c
a = 14.963 (2) Å
b = 4.632 (1) Å
c = 14.469 (2) Å
β = 103.612 (1)°
V = 974.7 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.35 mm⁻¹
T = 290 K
0.40 × 0.24 × 0.11 mm

Data collection

Oxford Xcalibur Eos(Nova) CCD detector diffractometer
Absorption correction: multi-scan (CrysAlis PRO RED; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO CCD and CrysAlis PRO RED. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]$ ) T_min = 0.871, T_max = 0.962
7607 measured reflections
1723 independent reflections
790 reflections with I > 2σ(I)
R_int = 0.167

Refinement

R[F² > 2σ(F²)] = 0.061
wR(F²) = 0.135
S = 0.85
1723 reflections
129 parameters
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O⋯O1ⁱ	0.82	1.90	2.712 (4)	174
C10—H10A⋯Cg1ⁱⁱ	0.97	2.75	3.557 (4)	141
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 $[Oxford Diffraction (2009). CrysAlis PRO CCD and CrysAlis PRO RED. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]$ ); cell refinement: CrysAlis PRO CCD; data reduction: CrysAlis PRO RED (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO CCD and CrysAlis PRO RED. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]$ ); 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/S1600536810020490/hb5470sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810020490/hb5470Isup2.hkl

checkCIF report

Comment top

As part of our program which aimed to develop new selective and environmentally friendly methodologies for the preparation of 2-chloroquinolines (Roopan et al., 2010), we report here crystal structure of the title compound, (I).

The title molecule (I), (Fig. 1), except the hydroxyl and methyl H atoms, close to planar (r.m.s deviation 0.017 Å). The values of the geometric parameters in (I) are comparable to those of some similar structures (Khan et al., 2009).

In the solid-state, the molecules are linked via intermolecular O—H···O hydrogen bonds (Table 1, Fig. 2). The crystal structure is further stabilized by an intermolecular C–H···π interactions between the methylene H atom of ethenol substituent and the pyridine ring of an adjacent molecule, with a C10–H10A···Cg1ⁱⁱ separation of 2.75 Å (Table 1, Cg1 is the centroid of N1/C1–C3/C8/C9 pyridine ring; symmetry code: (ii) x, y + 1, z). In addition, the packing mode results in stabilizing π-π stacking interactions [Cg1···Cg2ⁱⁱ = 3.661 (2) Å, where Cg1 and Cg2 are the centroids of the N1/C1–C3/C8/C9 and C4–C9 rings].

Related literature top

For a related structure and background references, see: Roopan et al. (2010). For a similar structure, see: Khan et al. (2009).

Experimental top

2-Chloro-8-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 4 min. Ethylacetate was poured into the reaction mixture and filtered off. The filtrated after removal of solvent ethy lacetate 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. The molecule of (I), showing 50% probability displacement ellipsoids.
	Fig. 2. A view of the packing of (I) with intermolecular O–H···O hydrogen bonding down the b axis. The H atoms not involved in hydrogen bonds have been omitted for clarity.

(2-Chloro-8-methylquinolin-3-yl)methanol top

Crystal data top

C₁₁H₁₀ClNO	F(000) = 432
M_r = 207.65	D_x = 1.415 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 972 reflections
a = 14.963 (2) Å	θ = 2.0–20.5°
b = 4.632 (1) Å	µ = 0.35 mm⁻¹
c = 14.469 (2) Å	T = 290 K
β = 103.612 (1)°	Plate, colourless
V = 974.7 (3) Å³	0.40 × 0.24 × 0.11 mm
Z = 4

Data collection top

Oxford Xcalibur Eos(Nova) CCD detector diffractometer	1723 independent reflections
Radiation source: Enhance (Mo) X-ray Source	790 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.167
ω scans	θ_max = 25.0°, θ_min = 2.9°
Absorption correction: multi-scan (CrysAlis PRO RED; Oxford Diffraction, 2009)	h = −17→17
T_min = 0.871, T_max = 0.962	k = −5→5
7607 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)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.135	H-atom parameters constrained
S = 0.85	w = 1/[σ²(F_o²) + (0.0492P)²] where P = (F_o² + 2F_c²)/3
1723 reflections	(Δ/σ)_max < 0.001
129 parameters	Δρ_max = 0.23 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₁₁H₁₀ClNO	V = 974.7 (3) Å³
M_r = 207.65	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 14.963 (2) Å	µ = 0.35 mm⁻¹
b = 4.632 (1) Å	T = 290 K
c = 14.469 (2) Å	0.40 × 0.24 × 0.11 mm
β = 103.612 (1)°

Data collection top

Oxford Xcalibur Eos(Nova) CCD detector diffractometer	1723 independent reflections
Absorption correction: multi-scan (CrysAlis PRO RED; Oxford Diffraction, 2009)	790 reflections with I > 2σ(I)
T_min = 0.871, T_max = 0.962	R_int = 0.167
7607 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.061	0 restraints
wR(F²) = 0.135	H-atom parameters constrained
S = 0.85	Δρ_max = 0.23 e Å⁻³
1723 reflections	Δρ_min = −0.23 e Å⁻³
129 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	0.13301 (8)	0.6900 (2)	−0.03546 (7)	0.0599 (5)
O1	0.0342 (2)	0.8800 (5)	0.2237 (2)	0.0534 (11)
N1	0.2487 (2)	0.3588 (7)	0.0784 (2)	0.0372 (11)
C1	0.1808 (3)	0.5392 (8)	0.0749 (2)	0.0368 (14)
C2	0.1436 (3)	0.6216 (7)	0.1526 (3)	0.0340 (14)
C3	0.1835 (3)	0.4990 (8)	0.2376 (3)	0.0398 (16)
C4	0.2981 (3)	0.1674 (9)	0.3335 (3)	0.0475 (17)
C5	0.3681 (3)	−0.0242 (10)	0.3370 (3)	0.0551 (17)
C6	0.3985 (3)	−0.0855 (9)	0.2554 (3)	0.0538 (17)
C7	0.3611 (3)	0.0351 (9)	0.1686 (3)	0.0427 (17)
C8	0.2875 (3)	0.2323 (8)	0.1643 (3)	0.0365 (12)
C9	0.2566 (3)	0.3003 (8)	0.2465 (3)	0.0369 (14)
C10	0.0635 (3)	0.8293 (8)	0.1397 (3)	0.0436 (16)
C11	0.3954 (3)	−0.0328 (10)	0.0817 (3)	0.0589 (17)
H1O	0.00970	0.73400	0.23830	0.0800*
H3	0.16230	0.54700	0.29100	0.0480*
H4	0.27790	0.20970	0.38810	0.0570*
H5	0.39560	−0.11390	0.39410	0.0660*
H6	0.44670	−0.21540	0.26010	0.0640*
H10A	0.08110	1.01170	0.11630	0.0520*
H10B	0.01230	0.75250	0.09200	0.0520*
H11A	0.44600	−0.16520	0.09810	0.0880*
H11B	0.41540	0.14190	0.05710	0.0880*
H11C	0.34680	−0.11840	0.03440	0.0880*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0614 (8)	0.0749 (9)	0.0457 (7)	0.0113 (7)	0.0170 (6)	0.0132 (6)
O1	0.060 (2)	0.0369 (17)	0.078 (2)	0.0016 (16)	0.0457 (18)	−0.0011 (16)
N1	0.042 (2)	0.035 (2)	0.0375 (19)	−0.0031 (18)	0.0153 (17)	−0.0004 (17)
C1	0.044 (3)	0.031 (2)	0.037 (2)	−0.007 (2)	0.013 (2)	−0.0008 (19)
C2	0.040 (3)	0.028 (2)	0.037 (2)	−0.005 (2)	0.015 (2)	−0.003 (2)
C3	0.044 (3)	0.043 (3)	0.039 (2)	−0.009 (2)	0.023 (2)	−0.006 (2)
C4	0.051 (3)	0.052 (3)	0.042 (3)	−0.010 (3)	0.016 (2)	0.000 (2)
C5	0.053 (3)	0.063 (3)	0.047 (3)	−0.004 (3)	0.007 (2)	0.012 (2)
C6	0.038 (3)	0.051 (3)	0.071 (3)	−0.001 (2)	0.010 (3)	0.011 (3)
C7	0.037 (3)	0.044 (3)	0.048 (3)	−0.006 (2)	0.012 (2)	0.002 (2)
C8	0.037 (2)	0.036 (2)	0.038 (2)	−0.007 (2)	0.012 (2)	−0.002 (2)
C9	0.043 (3)	0.036 (2)	0.034 (2)	−0.007 (2)	0.014 (2)	−0.003 (2)
C10	0.046 (3)	0.038 (2)	0.053 (3)	−0.004 (2)	0.024 (2)	−0.002 (2)
C11	0.050 (3)	0.069 (3)	0.063 (3)	0.010 (3)	0.024 (2)	−0.006 (3)

Geometric parameters (Å, º) top

Cl1—C1	1.735 (3)	C7—C11	1.499 (6)
O1—C10	1.406 (5)	C7—C8	1.421 (6)
O1—H1O	0.8200	C8—C9	1.409 (6)
N1—C8	1.373 (5)	C3—H3	0.9300
N1—C1	1.307 (5)	C4—H4	0.9300
C1—C2	1.419 (6)	C5—H5	0.9300
C2—C10	1.514 (6)	C6—H6	0.9300
C2—C3	1.359 (6)	C10—H10A	0.9700
C3—C9	1.412 (6)	C10—H10B	0.9700
C4—C9	1.408 (6)	C11—H11A	0.9600
C4—C5	1.365 (6)	C11—H11B	0.9600
C5—C6	1.391 (6)	C11—H11C	0.9600
C6—C7	1.368 (6)

C10—O1—H1O	110.00	O1—C10—C2	113.5 (3)
C1—N1—C8	117.8 (3)	C2—C3—H3	119.00
Cl1—C1—N1	116.2 (3)	C9—C3—H3	119.00
Cl1—C1—C2	117.9 (3)	C5—C4—H4	120.00
N1—C1—C2	126.0 (3)	C9—C4—H4	120.00
C1—C2—C3	115.7 (4)	C4—C5—H5	120.00
C1—C2—C10	121.3 (4)	C6—C5—H5	120.00
C3—C2—C10	122.9 (4)	C5—C6—H6	118.00
C2—C3—C9	121.4 (4)	C7—C6—H6	118.00
C5—C4—C9	119.4 (4)	O1—C10—H10A	109.00
C4—C5—C6	120.2 (4)	O1—C10—H10B	109.00
C5—C6—C7	123.4 (4)	C2—C10—H10A	109.00
C6—C7—C11	122.5 (4)	C2—C10—H10B	109.00
C8—C7—C11	120.9 (4)	H10A—C10—H10B	108.00
C6—C7—C8	116.6 (4)	C7—C11—H11A	109.00
N1—C8—C9	121.0 (4)	C7—C11—H11B	109.00
C7—C8—C9	120.8 (4)	C7—C11—H11C	109.00
N1—C8—C7	118.2 (4)	H11A—C11—H11B	109.00
C3—C9—C4	122.4 (4)	H11A—C11—H11C	109.00
C4—C9—C8	119.6 (4)	H11B—C11—H11C	110.00
C3—C9—C8	118.0 (4)

C8—N1—C1—Cl1	−179.2 (3)	C9—C4—C5—C6	0.5 (7)
C8—N1—C1—C2	1.0 (6)	C5—C4—C9—C3	179.6 (4)
C1—N1—C8—C7	179.8 (4)	C5—C4—C9—C8	0.4 (6)
C1—N1—C8—C9	−1.5 (6)	C4—C5—C6—C7	−0.7 (7)
Cl1—C1—C2—C3	−179.7 (3)	C5—C6—C7—C8	0.0 (7)
Cl1—C1—C2—C10	1.3 (5)	C5—C6—C7—C11	179.6 (4)
N1—C1—C2—C3	0.1 (6)	C6—C7—C8—N1	179.6 (4)
N1—C1—C2—C10	−178.9 (4)	C6—C7—C8—C9	0.9 (6)
C1—C2—C3—C9	−0.7 (6)	C11—C7—C8—N1	0.0 (6)
C10—C2—C3—C9	178.3 (4)	C11—C7—C8—C9	−178.7 (4)
C1—C2—C10—O1	178.4 (3)	N1—C8—C9—C3	1.0 (6)
C3—C2—C10—O1	−0.6 (5)	N1—C8—C9—C4	−179.8 (4)
C2—C3—C9—C4	−179.1 (4)	C7—C8—C9—C3	179.7 (4)
C2—C3—C9—C8	0.1 (6)	C7—C8—C9—C4	−1.1 (6)

Hydrogen-bond geometry (Å, º) top

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

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···O1ⁱ	0.82	1.90	2.712 (4)	174
C10—H10A···Cg1ⁱⁱ	0.97	2.75	3.557 (4)	141

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)	290
a, b, c (Å)	14.963 (2), 4.632 (1), 14.469 (2)
β (°)	103.612 (1)
V (Å³)	974.7 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.35
Crystal size (mm)	0.40 × 0.24 × 0.11

Data collection
Diffractometer	Oxford Xcalibur Eos(Nova) CCD detector diffractometer
Absorption correction	Multi-scan (CrysAlis PRO RED; Oxford Diffraction, 2009)
T_min, T_max	0.871, 0.962
No. of measured, independent and observed [I > 2σ(I)] reflections	7607, 1723, 790
R_int	0.167
(sin θ/λ)_max (Å⁻¹)	0.594

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.061, 0.135, 0.85
No. of reflections	1723
No. of parameters	129
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.23

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

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···O1ⁱ	0.82	1.90	2.712 (4)	174
C10—H10A···Cg1ⁱⁱ	0.97	2.75	3.557 (4)	141

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 the 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

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., Kushwaha, A. K., Hathwar, V. R. & Ng, S. W. (2009). Acta Cryst. E65, o2722. Web of Science CrossRef IUCr Journals Google Scholar
Oxford Diffraction (2009). CrysAlis PRO CCD and CrysAlis PRO RED. Oxford Diffraction Ltd, Yarnton, Oxfordshire, 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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CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 7| July 2010| Page o1543

doi:10.1107/S1600536810020490

Open

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