2-Chloro-3-hydroxy-methyl-7,8-dimethyl-quinoline.

All non-H atoms of the title compound, C(12)H(12)ClNO, are co-planar (r.m.s. deviation = 0.055 Å). The hydr-oxy H atom is disordered over two positions of equal occupancy. In the crystal, mol-ecules are linked by O-H⋯O hydrogen bonds, generating zigzag chains running along the b 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

C12H12ClNO

M = 221.68

Monoclinic,

a = 17.4492 (12) Å

b = 4.6271 (2) Å

c = 14.3773 (7) Å

β = 113.297 (7)°

V = 1066.17 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.33 mm−1

T = 293 K

0.38 × 0.15 × 0.06 mm

Data collection

Bruker SMART area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.885, T max = 0.981

10456 measured reflections

1884 independent reflections

1488 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.094

S = 1.05

1884 reflections

139 parameters

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.22 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/S160053680905404X/bt5139sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680905404X/bt5139Isup2.hkl

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

C12H12ClNO	F(000) = 464
Mr = 221.68	Dx = 1.381 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 963 reflections
a = 17.4492 (12) Å	θ = 3.1–25.0°
b = 4.6271 (2) Å	µ = 0.33 mm−1
c = 14.3773 (7) Å	T = 293 K
β = 113.297 (7)°	Plate, colorless
V = 1066.17 (10) Å3	0.38 × 0.15 × 0.06 mm
Z = 4

Bruker SMART area-detector diffractometer	1884 independent reflections
Radiation source: fine-focus sealed tube	1488 reflections with I > 2σ(I)
graphite	Rint = 0.033
φ and ω scans	θmax = 25.0°, θmin = 3.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −20→20
Tmin = 0.885, Tmax = 0.981	k = −5→5
10456 measured reflections	l = −17→17

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.094	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0496P)2 + 0.1434P] where P = (Fo2 + 2Fc2)/3
1884 reflections	(Δ/σ)max = 0.001
139 parameters	Δρmax = 0.16 e Å−3
0 restraints	Δρmin = −0.22 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

	x	y	z	Uiso*/Ueq	Occ. (<1)
Cl1	0.37792 (3)	0.62190 (11)	0.12385 (3)	0.0547 (2)
O1	0.46228 (9)	0.7503 (3)	0.45560 (9)	0.0578 (4)
H1A	0.4892	0.8991	0.4763	0.087*	0.50
H1B	0.4914	0.6102	0.4824	0.087*	0.50
N1	0.27105 (9)	0.2833 (3)	0.15172 (10)	0.0365 (3)
C1	0.33144 (11)	0.4587 (4)	0.19891 (12)	0.0361 (4)
C2	0.36337 (11)	0.5327 (3)	0.30325 (12)	0.0365 (4)
C3	0.32309 (11)	0.4071 (3)	0.35710 (12)	0.0381 (4)
H3	0.3403	0.4493	0.4256	0.046*
C4	0.25620 (10)	0.2154 (4)	0.31127 (12)	0.0349 (4)
C5	0.21258 (12)	0.0807 (4)	0.36385 (13)	0.0427 (5)
H5	0.2273	0.1186	0.4323	0.051*
C6	0.14924 (12)	−0.1037 (4)	0.31451 (13)	0.0440 (5)
H6	0.1210	−0.1899	0.3502	0.053*
C7	0.12436 (11)	−0.1703 (4)	0.21072 (13)	0.0398 (4)
C8	0.16551 (11)	−0.0432 (4)	0.15657 (12)	0.0370 (4)
C9	0.23169 (10)	0.1536 (3)	0.20687 (12)	0.0333 (4)
C10	0.43655 (11)	0.7321 (4)	0.34903 (13)	0.0454 (5)
H10A	0.4825	0.6623	0.3334	0.054*
H10B	0.4215	0.9231	0.3196	0.054*
C11	0.05264 (12)	−0.3765 (4)	0.16298 (16)	0.0558 (5)
H11A	0.0510	−0.4393	0.0986	0.084*	0.50
H11B	0.0013	−0.2809	0.1535	0.084*	0.50
H11C	0.0599	−0.5409	0.2064	0.084*	0.50
H11D	0.0238	−0.4015	0.2071	0.084*	0.50
H11E	0.0735	−0.5598	0.1521	0.084*	0.50
H11F	0.0149	−0.2998	0.0993	0.084*	0.50
C12	0.14234 (13)	−0.1070 (4)	0.04636 (13)	0.0516 (5)
H12A	0.1910	−0.1694	0.0363	0.077*	0.50
H12B	0.1203	0.0644	0.0073	0.077*	0.50
H12C	0.1009	−0.2568	0.0250	0.077*	0.50
H12D	0.0838	−0.0718	0.0095	0.077*	0.50
H12E	0.1545	−0.3056	0.0384	0.077*	0.50
H12F	0.1739	0.0156	0.0207	0.077*	0.50

	U11	U22	U33	U12	U13	U23
Cl1	0.0522 (3)	0.0662 (4)	0.0492 (3)	−0.0064 (2)	0.0237 (2)	0.0071 (2)
O1	0.0632 (9)	0.0508 (8)	0.0438 (7)	−0.0109 (7)	0.0045 (6)	−0.0114 (6)
N1	0.0374 (9)	0.0395 (8)	0.0307 (7)	0.0031 (7)	0.0116 (6)	0.0004 (6)
C1	0.0360 (10)	0.0362 (10)	0.0357 (9)	0.0056 (8)	0.0138 (8)	0.0032 (7)
C2	0.0369 (10)	0.0313 (9)	0.0366 (9)	0.0060 (8)	0.0094 (8)	−0.0016 (7)
C3	0.0420 (11)	0.0384 (10)	0.0283 (8)	0.0051 (8)	0.0078 (7)	−0.0053 (7)
C4	0.0375 (10)	0.0344 (9)	0.0308 (8)	0.0068 (8)	0.0113 (7)	−0.0004 (7)
C5	0.0478 (11)	0.0506 (12)	0.0310 (9)	0.0050 (9)	0.0169 (8)	0.0009 (8)
C6	0.0431 (11)	0.0482 (11)	0.0438 (10)	0.0061 (9)	0.0203 (8)	0.0099 (8)
C7	0.0345 (10)	0.0368 (10)	0.0439 (10)	0.0062 (8)	0.0110 (8)	0.0054 (8)
C8	0.0370 (10)	0.0361 (10)	0.0320 (9)	0.0055 (8)	0.0075 (7)	0.0004 (7)
C9	0.0351 (10)	0.0335 (9)	0.0293 (8)	0.0060 (8)	0.0105 (7)	0.0007 (7)
C10	0.0448 (12)	0.0382 (10)	0.0463 (10)	−0.0017 (9)	0.0107 (8)	−0.0033 (8)
C11	0.0454 (12)	0.0536 (13)	0.0631 (13)	−0.0041 (10)	0.0157 (10)	0.0039 (10)
C12	0.0547 (13)	0.0576 (13)	0.0342 (9)	−0.0056 (10)	0.0087 (9)	−0.0064 (8)

Cl1—C1	1.7563 (17)	C7—C11	1.506 (3)
O1—C10	1.418 (2)	C8—C9	1.423 (2)
O1—H1A	0.8200	C8—C12	1.501 (2)
O1—H1B	0.8200	C10—H10A	0.9700
N1—C1	1.290 (2)	C10—H10B	0.9700
N1—C9	1.375 (2)	C11—H11A	0.9600
C1—C2	1.420 (2)	C11—H11B	0.9600
C2—C3	1.364 (2)	C11—H11C	0.9600
C2—C10	1.500 (2)	C11—H11D	0.9600
C3—C4	1.405 (2)	C11—H11E	0.9600
C3—H3	0.9300	C11—H11F	0.9600
C4—C5	1.412 (2)	C12—H12A	0.9600
C4—C9	1.418 (2)	C12—H12B	0.9600
C5—C6	1.354 (3)	C12—H12C	0.9600
C5—H5	0.9300	C12—H12D	0.9600
C6—C7	1.413 (2)	C12—H12E	0.9600
C6—H6	0.9300	C12—H12F	0.9600
C7—C8	1.382 (2)
C10—O1—H1A	109.5	O1—C10—C2	111.18 (14)
C10—O1—H1B	109.5	O1—C10—H10A	109.4
C1—N1—C9	117.49 (14)	C2—C10—H10A	109.4
N1—C1—C2	127.22 (15)	O1—C10—H10B	109.4
N1—C1—Cl1	115.28 (12)	C2—C10—H10B	109.4
C2—C1—Cl1	117.51 (13)	H10A—C10—H10B	108.0
C3—C2—C1	114.95 (16)	C7—C11—H11A	109.5
C3—C2—C10	123.59 (15)	C7—C11—H11B	109.5
C1—C2—C10	121.46 (15)	H11A—C11—H11B	109.5
C2—C3—C4	121.44 (15)	C7—C11—H11C	109.5
C2—C3—H3	119.3	H11A—C11—H11C	109.5
C4—C3—H3	119.3	H11B—C11—H11C	109.5
C3—C4—C5	123.44 (15)	C7—C11—H11D	109.5
C3—C4—C9	118.06 (15)	C7—C11—H11E	109.5
C5—C4—C9	118.49 (16)	H11D—C11—H11E	109.5
C6—C5—C4	119.92 (16)	C7—C11—H11F	109.5
C6—C5—H5	120.0	H11D—C11—H11F	109.5
C4—C5—H5	120.0	H11E—C11—H11F	109.5
C5—C6—C7	122.47 (16)	C8—C12—H12A	109.5
C5—C6—H6	118.8	C8—C12—H12B	109.5
C7—C6—H6	118.8	H12A—C12—H12B	109.5
C8—C7—C6	119.41 (16)	C8—C12—H12C	109.5
C8—C7—C11	122.41 (16)	H12A—C12—H12C	109.5
C6—C7—C11	118.17 (16)	H12B—C12—H12C	109.5
C7—C8—C9	118.95 (15)	C8—C12—H12D	109.5
C7—C8—C12	121.87 (16)	C8—C12—H12E	109.5
C9—C8—C12	119.19 (15)	H12D—C12—H12E	109.5
N1—C9—C4	120.81 (15)	C8—C12—H12F	109.5
N1—C9—C8	118.43 (14)	H12D—C12—H12F	109.5
C4—C9—C8	120.75 (15)	H12E—C12—H12F	109.5

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1a···O1i	0.82	1.91	2.715 (3)	167
O1—H1b···O1ii	0.82	1.91	2.720 (3)	168

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1a⋯O1i	0.82	1.91	2.715 (3)	167
O1—H1b⋯O1ii	0.82	1.91	2.720 (3)	168

Symmetry codes: (i) ; (ii) .