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

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.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.007 Å
• R factor = 0.085
• wR factor = 0.222
• Data-to-parameter ratio = 13.1

checkCIF/PLATON results

No syntax errors found



Alert level C
RINTA01_ALERT_3_C  The value of Rint is greater than 0.12
            Rint given   0.136
PLAT020_ALERT_3_C The value of Rint is greater than 0.12 .........       0.14
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C6     --  C7      ..       5.38 su
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.39
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds (x 1000) Ang ..          6
PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) .....          3
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.594         25

Alert level G
PLAT072_ALERT_2_G SHELXL First Parameter in WGHT Unusually Large.       0.14

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   7 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   5 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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S1. 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].

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).

S2. 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.

S3. 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.

Computing details

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

	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

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) Å^3	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 monochromator	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 F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.085	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.222	H atoms treated by a mixture of independent and constrained refinement
S = 0.94	w = 1/[σ^2(Fo^2) + (0.1359P)^2] where P = (Fo^2 + 2Fc^2)/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)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

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···O1^i	0.79 (6)	1.93 (6)	2.716 (5)	177 (7)
C10—H10A···Cg1^ii	0.97	2.73	3.526 (5)	139

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