2-Chloro-3-hydroxy-methyl-6-methoxy-quinoline.

All the non-H atoms of the title compound, C(11)H(10)ClNO(2), are roughly coplanar (r.m.s. deviation = 0.058 Å). In the crystal, adjacent mol-ecules are linked by an O-H⋯N hydrogen bond, generating chains running along the a axis.

Related literature

Substituted quinoline-3-carbaldehydes are inter­mediates for annelation and functional group modification; for a review of the synthesis of quinolines by the Vilsmeier–Haack reaction, see: Meth-Cohn (1993 ▶).

Experimental

Crystal data

C11H10ClNO2

M = 223.65

Monoclinic,

a = 6.9738 (3) Å

b = 21.4668 (9) Å

c = 7.3479 (4) Å

β = 108.220 (5)°

V = 1044.87 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.34 mm−1

T = 293 K

0.28 × 0.21 × 0.20 mm

Data collection

Bruker SMART area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.910, T max = 0.935

11517 measured reflections

2348 independent reflections

1487 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.108

S = 0.97

2348 reflections

138 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.25 e Å−3

Data collection: SMART (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809054051/bt5140sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809054051/bt5140Isup2.hkl

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

C11H10ClNO2	F(000) = 464
Mr = 223.65	Dx = 1.422 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1941 reflections
a = 6.9738 (3) Å	θ = 3.1–25.5°
b = 21.4668 (9) Å	µ = 0.34 mm−1
c = 7.3479 (4) Å	T = 293 K
β = 108.220 (5)°	Block, colorless
V = 1044.87 (8) Å3	0.28 × 0.21 × 0.20 mm
Z = 4

Bruker SMART area-detector diffractometer	2348 independent reflections
Radiation source: fine-focus sealed tube	1487 reflections with I > 2σ(I)
graphite	Rint = 0.035
φ and ω scans	θmax = 27.5°, θmin = 3.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→8
Tmin = 0.910, Tmax = 0.935	k = −26→27
11517 measured reflections	l = −9→9

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.108	H-atom parameters constrained
S = 0.97	w = 1/[σ2(Fo2) + (0.058P)2] where P = (Fo2 + 2Fc2)/3
2348 reflections	(Δ/σ)max = 0.001
138 parameters	Δρmax = 0.21 e Å−3
0 restraints	Δρmin = −0.25 e Å−3

	x	y	z	Uiso*/Ueq
Cl1	0.33210 (8)	0.65210 (2)	0.10064 (7)	0.0648 (2)
O1	0.97027 (18)	0.59162 (7)	0.33602 (19)	0.0672 (4)
H1	1.0200	0.5790	0.2554	0.101*
O2	0.4314 (2)	0.29302 (7)	0.3876 (2)	0.0766 (5)
N1	0.2607 (2)	0.53770 (7)	0.16969 (18)	0.0446 (4)
C1	0.4061 (3)	0.57605 (8)	0.1763 (2)	0.0430 (4)
C2	0.6156 (2)	0.56246 (8)	0.2401 (2)	0.0408 (4)
C3	0.6650 (2)	0.50291 (8)	0.2994 (2)	0.0437 (4)
H3	0.8004	0.4916	0.3461	0.052*
C4	0.5149 (2)	0.45775 (8)	0.2917 (2)	0.0390 (4)
C5	0.5600 (3)	0.39542 (9)	0.3483 (2)	0.0494 (5)
H5	0.6935	0.3821	0.3926	0.059*
C6	0.4070 (3)	0.35449 (9)	0.3379 (2)	0.0526 (5)
C7	0.2053 (3)	0.37443 (9)	0.2741 (2)	0.0546 (5)
H7	0.1027	0.3463	0.2698	0.065*
C8	0.1583 (3)	0.43397 (9)	0.2189 (2)	0.0507 (5)
H8	0.0238	0.4463	0.1758	0.061*
C9	0.3120 (2)	0.47761 (8)	0.2261 (2)	0.0405 (4)
C10	0.7702 (3)	0.61178 (9)	0.2442 (3)	0.0528 (5)
H10A	0.7575	0.6240	0.1138	0.063*
H10B	0.7430	0.6482	0.3103	0.063*
C11	0.6296 (4)	0.26820 (11)	0.4324 (4)	0.0912 (8)
H11A	0.6799	0.2747	0.3263	0.137*
H11B	0.6264	0.2244	0.4573	0.137*
H11C	0.7163	0.2887	0.5439	0.137*

	U11	U22	U33	U12	U13	U23
Cl1	0.0574 (3)	0.0603 (3)	0.0736 (4)	0.0151 (2)	0.0158 (3)	0.0111 (3)
O1	0.0365 (8)	0.0931 (11)	0.0762 (9)	−0.0030 (7)	0.0235 (7)	−0.0079 (8)
O2	0.0887 (12)	0.0522 (9)	0.0807 (10)	0.0010 (8)	0.0147 (8)	0.0016 (7)
N1	0.0306 (8)	0.0591 (9)	0.0412 (8)	0.0057 (7)	0.0069 (6)	−0.0035 (7)
C1	0.0389 (10)	0.0539 (10)	0.0365 (9)	0.0122 (8)	0.0123 (8)	−0.0006 (8)
C2	0.0347 (9)	0.0573 (11)	0.0341 (8)	0.0033 (8)	0.0161 (7)	−0.0036 (8)
C3	0.0277 (9)	0.0628 (11)	0.0403 (9)	0.0106 (8)	0.0103 (7)	−0.0021 (8)
C4	0.0328 (9)	0.0524 (10)	0.0307 (8)	0.0059 (8)	0.0083 (7)	−0.0051 (7)
C5	0.0420 (11)	0.0593 (12)	0.0428 (10)	0.0127 (9)	0.0076 (8)	−0.0032 (9)
C6	0.0589 (13)	0.0534 (12)	0.0427 (10)	−0.0005 (9)	0.0119 (9)	−0.0073 (9)
C7	0.0504 (12)	0.0631 (13)	0.0476 (10)	−0.0115 (10)	0.0115 (9)	−0.0095 (9)
C8	0.0334 (10)	0.0698 (13)	0.0443 (10)	−0.0022 (9)	0.0056 (8)	−0.0093 (9)
C9	0.0334 (9)	0.0559 (11)	0.0304 (8)	0.0047 (8)	0.0070 (7)	−0.0069 (8)
C10	0.0433 (11)	0.0653 (12)	0.0547 (11)	0.0001 (9)	0.0223 (9)	0.0013 (10)
C11	0.113 (2)	0.0600 (14)	0.1016 (18)	0.0275 (14)	0.0342 (16)	0.0121 (13)

Cl1—C1	1.7496 (18)	C4—C9	1.411 (2)
O1—C10	1.414 (2)	C5—C6	1.366 (2)
O1—H1	0.8200	C5—H5	0.9300
O2—C6	1.366 (2)	C6—C7	1.403 (3)
O2—C11	1.421 (3)	C7—C8	1.350 (3)
N1—C1	1.295 (2)	C7—H7	0.9300
N1—C9	1.368 (2)	C8—C9	1.412 (2)
C1—C2	1.418 (2)	C8—H8	0.9300
C2—C3	1.360 (2)	C10—H10A	0.9700
C2—C10	1.505 (2)	C10—H10B	0.9700
C3—C4	1.415 (2)	C11—H11A	0.9600
C3—H3	0.9300	C11—H11B	0.9600
C4—C5	1.407 (2)	C11—H11C	0.9600
C10—O1—H1	109.5	C8—C7—C6	120.86 (18)
C6—O2—C11	117.08 (18)	C8—C7—H7	119.6
C1—N1—C9	117.42 (14)	C6—C7—H7	119.6
N1—C1—C2	126.53 (16)	C7—C8—C9	120.44 (17)
N1—C1—Cl1	115.57 (13)	C7—C8—H8	119.8
C2—C1—Cl1	117.90 (14)	C9—C8—H8	119.8
C3—C2—C1	115.52 (16)	N1—C9—C4	121.87 (16)
C3—C2—C10	123.17 (16)	N1—C9—C8	119.38 (15)
C1—C2—C10	121.30 (16)	C4—C9—C8	118.75 (16)
C2—C3—C4	121.42 (16)	O1—C10—C2	112.82 (16)
C2—C3—H3	119.3	O1—C10—H10A	109.0
C4—C3—H3	119.3	C2—C10—H10A	109.0
C5—C4—C9	119.71 (16)	O1—C10—H10B	109.0
C5—C4—C3	123.07 (16)	C2—C10—H10B	109.0
C9—C4—C3	117.21 (15)	H10A—C10—H10B	107.8
C6—C5—C4	119.79 (17)	O2—C11—H11A	109.5
C6—C5—H5	120.1	O2—C11—H11B	109.5
C4—C5—H5	120.1	H11A—C11—H11B	109.5
O2—C6—C5	125.23 (18)	O2—C11—H11C	109.5
O2—C6—C7	114.34 (18)	H11A—C11—H11C	109.5
C5—C6—C7	120.43 (18)	H11B—C11—H11C	109.5
C9—N1—C1—C2	−1.4 (2)	C4—C5—C6—C7	−1.1 (3)
C9—N1—C1—Cl1	179.45 (10)	O2—C6—C7—C8	−179.55 (16)
N1—C1—C2—C3	0.1 (2)	C5—C6—C7—C8	1.1 (3)
Cl1—C1—C2—C3	179.24 (12)	C6—C7—C8—C9	−0.6 (3)
N1—C1—C2—C10	−178.78 (16)	C1—N1—C9—C4	0.9 (2)
Cl1—C1—C2—C10	0.4 (2)	C1—N1—C9—C8	−179.17 (15)
C1—C2—C3—C4	1.7 (2)	C5—C4—C9—N1	179.93 (14)
C10—C2—C3—C4	−179.43 (15)	C3—C4—C9—N1	0.8 (2)
C2—C3—C4—C5	178.76 (15)	C5—C4—C9—C8	0.0 (2)
C2—C3—C4—C9	−2.1 (2)	C3—C4—C9—C8	−179.16 (14)
C9—C4—C5—C6	0.5 (2)	C7—C8—C9—N1	−179.89 (15)
C3—C4—C5—C6	179.60 (16)	C7—C8—C9—C4	0.1 (2)
C11—O2—C6—C5	−7.7 (3)	C3—C2—C10—O1	−6.8 (2)
C11—O2—C6—C7	173.00 (17)	C1—C2—C10—O1	171.94 (14)
C4—C5—C6—O2	179.68 (15)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1i	0.82	2.16	2.913 (2)	153

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1i	0.82	2.16	2.913 (2)	153

Symmetry code: (i) .