2-Chloro-benzo[h]quinoline-3-carbaldehyde.

The benzo[h]quinolinyl fused-ring of the title compound, C(14)H(8)ClNO, is planar (r.m.s. deviation = 0.016 Å); the formyl group is slightly bent out of the plane [the C-C-C-O torsion angle is 10.7 (4)°].

Related literature

For a review of the synthesis of quinolines by the Vilsmeier–Haack reaction, see: Meth-Cohn (1993 ▶).

Experimental

Crystal data

C14H8ClNO

M = 241.66

Monoclinic,

a = 3.9833 (2) Å

b = 12.4722 (6) Å

c = 21.4561 (13) Å

β = 90.687 (6)°

V = 1065.87 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.34 mm−1

T = 290 K

0.20 × 0.15 × 0.15 mm

Data collection

Oxford Diffraction Excalibur diffractometer

Absorption correction: multi-scan (CrysAlis Pro; Oxford Diffraction, 2009 ▶) T min = 0.936, T max = 0.951

12099 measured reflections

1872 independent reflections

935 reflections with I > 2˘I)

R int = 0.093

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.087

S = 0.81

1872 reflections

154 parameters

H-atom parameters constrained

Δρmax = 0.14 e Å−3

Δρmin = −0.19 e Å−3

Data collection: CrysAlis Pro (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis Pro; data reduction: CrysAlis Pro; 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, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809040720/tk2551sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809040720/tk2551Isup2.hkl

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

C14H8ClNO	F(000) = 496
Mr = 241.66	Dx = 1.506 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1012 reflections
a = 3.9833 (2) Å	θ = 1.9–20.4°
b = 12.4722 (6) Å	µ = 0.34 mm−1
c = 21.4561 (13) Å	T = 290 K
β = 90.687 (6)°	Block, colorless
V = 1065.87 (10) Å3	0.20 × 0.15 × 0.15 mm
Z = 4

Oxford Diffraction Excalibur diffractometer	1872 independent reflections
Radiation source: fine-focus sealed tube	935 reflections with I > 2˘I)
graphite	Rint = 0.093
ω scans	θmax = 25.0°, θmin = 3.3°
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	h = −4→4
Tmin = 0.936, Tmax = 0.951	k = −14→14
12099 measured reflections	l = −25→25

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) = 0.087	H-atom parameters constrained
S = 0.81	w = 1/[σ2(Fo2) + (0.0379P)2] where P = (Fo2 + 2Fc2)/3
1872 reflections	(Δ/σ)max = 0.001
154 parameters	Δρmax = 0.14 e Å−3
0 restraints	Δρmin = −0.19 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
Cl1	0.74845 (19)	0.87817 (5)	0.54210 (3)	0.0598 (3)
O1	0.1454 (5)	0.63739 (16)	0.45218 (9)	0.0658 (6)
N1	0.7413 (5)	0.74695 (15)	0.63554 (10)	0.0385 (6)
C1	0.6418 (6)	0.75706 (19)	0.57774 (13)	0.0390 (7)
C2	0.4576 (6)	0.6809 (2)	0.54353 (12)	0.0380 (7)
C3	0.3790 (6)	0.58737 (19)	0.57384 (12)	0.0399 (7)
H3	0.2557	0.5348	0.5531	0.048*
C4	0.4818 (6)	0.57031 (19)	0.63539 (12)	0.0347 (7)
C5	0.4052 (6)	0.4751 (2)	0.66944 (13)	0.0414 (7)
H5	0.2857	0.4201	0.6501	0.050*
C6	0.5043 (6)	0.4643 (2)	0.72937 (13)	0.0431 (7)
H6	0.4504	0.4018	0.7506	0.052*
C7	0.6893 (6)	0.5458 (2)	0.76127 (12)	0.0360 (7)
C8	0.7886 (6)	0.5348 (2)	0.82389 (13)	0.0473 (8)
H8	0.7339	0.4725	0.8453	0.057*
C9	0.9636 (7)	0.6135 (2)	0.85384 (13)	0.0513 (8)
H9	1.0257	0.6051	0.8955	0.062*
C10	1.0497 (6)	0.7069 (2)	0.82201 (13)	0.0474 (7)
H10	1.1693	0.7606	0.8426	0.057*
C11	0.9598 (6)	0.7202 (2)	0.76084 (12)	0.0388 (7)
H11	1.0219	0.7822	0.7399	0.047*
C12	0.7750 (6)	0.64093 (19)	0.72954 (12)	0.0319 (6)
C13	0.6639 (6)	0.65335 (19)	0.66560 (12)	0.0335 (7)
C14	0.3425 (7)	0.6954 (2)	0.47811 (14)	0.0496 (8)
H14	0.4283	0.7530	0.4558	0.060*

	U11	U22	U33	U12	U13	U23
Cl1	0.0849 (6)	0.0483 (5)	0.0463 (5)	−0.0102 (4)	−0.0001 (4)	0.0101 (4)
O1	0.0809 (16)	0.0710 (15)	0.0450 (14)	−0.0128 (12)	−0.0151 (12)	−0.0047 (12)
N1	0.0463 (15)	0.0353 (14)	0.0341 (15)	−0.0004 (10)	0.0016 (11)	−0.0006 (11)
C1	0.0404 (17)	0.0381 (16)	0.0387 (18)	−0.0002 (13)	0.0065 (14)	−0.0006 (14)
C2	0.0378 (17)	0.0421 (17)	0.0342 (18)	0.0034 (14)	0.0058 (14)	−0.0006 (14)
C3	0.0380 (16)	0.0431 (18)	0.0386 (18)	−0.0005 (13)	−0.0012 (14)	−0.0101 (14)
C4	0.0341 (16)	0.0356 (16)	0.0344 (18)	0.0033 (13)	0.0031 (13)	−0.0056 (14)
C5	0.0420 (17)	0.0370 (17)	0.0452 (19)	−0.0014 (13)	−0.0003 (15)	−0.0032 (15)
C6	0.0406 (17)	0.0362 (16)	0.053 (2)	0.0025 (14)	0.0051 (15)	0.0069 (15)
C7	0.0339 (16)	0.0377 (16)	0.0367 (18)	0.0071 (13)	0.0059 (14)	0.0009 (14)
C8	0.0514 (19)	0.0481 (18)	0.043 (2)	0.0077 (15)	0.0037 (15)	0.0110 (15)
C9	0.059 (2)	0.064 (2)	0.0311 (17)	0.0077 (17)	−0.0036 (15)	0.0004 (17)
C10	0.0527 (19)	0.0489 (18)	0.040 (2)	0.0048 (15)	−0.0053 (15)	−0.0048 (16)
C11	0.0417 (17)	0.0360 (16)	0.0385 (18)	0.0054 (13)	−0.0002 (14)	−0.0013 (14)
C12	0.0281 (15)	0.0329 (16)	0.0349 (17)	0.0069 (12)	0.0017 (13)	−0.0020 (13)
C13	0.0314 (16)	0.0347 (16)	0.0347 (17)	0.0045 (12)	0.0057 (13)	−0.0003 (13)
C14	0.058 (2)	0.053 (2)	0.0383 (19)	0.0027 (16)	0.0012 (16)	0.0024 (16)

Cl1—C1	1.748 (3)	C6—H6	0.9300
O1—C14	1.200 (3)	C7—C8	1.403 (3)
N1—C1	1.303 (3)	C7—C12	1.412 (3)
N1—C13	1.371 (3)	C8—C9	1.361 (3)
C1—C2	1.402 (3)	C8—H8	0.9300
C2—C3	1.374 (3)	C9—C10	1.395 (3)
C2—C14	1.483 (3)	C9—H9	0.9300
C3—C4	1.394 (3)	C10—C11	1.366 (3)
C3—H3	0.9300	C10—H10	0.9300
C4—C13	1.417 (3)	C11—C12	1.399 (3)
C4—C5	1.429 (3)	C11—H11	0.9300
C5—C6	1.347 (3)	C12—C13	1.445 (3)
C5—H5	0.9300	C14—H14	0.9300
C6—C7	1.426 (3)
C1—N1—C13	117.6 (2)	C9—C8—C7	121.2 (3)
N1—C1—C2	125.7 (2)	C9—C8—H8	119.4
N1—C1—Cl1	115.3 (2)	C7—C8—H8	119.4
C2—C1—Cl1	119.0 (2)	C8—C9—C10	119.9 (3)
C3—C2—C1	116.6 (2)	C8—C9—H9	120.0
C3—C2—C14	118.8 (3)	C10—C9—H9	120.0
C1—C2—C14	124.5 (3)	C11—C10—C9	120.5 (3)
C2—C3—C4	120.8 (2)	C11—C10—H10	119.7
C2—C3—H3	119.6	C9—C10—H10	119.7
C4—C3—H3	119.6	C10—C11—C12	120.4 (3)
C3—C4—C13	117.7 (2)	C10—C11—H11	119.8
C3—C4—C5	123.3 (3)	C12—C11—H11	119.8
C13—C4—C5	119.0 (2)	C11—C12—C7	119.4 (2)
C6—C5—C4	120.6 (3)	C11—C12—C13	122.2 (2)
C6—C5—H5	119.7	C7—C12—C13	118.4 (2)
C4—C5—H5	119.7	N1—C13—C4	121.6 (2)
C5—C6—C7	122.1 (3)	N1—C13—C12	118.0 (2)
C5—C6—H6	119.0	C4—C13—C12	120.4 (2)
C7—C6—H6	119.0	O1—C14—C2	124.0 (3)
C8—C7—C12	118.5 (2)	O1—C14—H14	118.0
C8—C7—C6	121.9 (3)	C2—C14—H14	118.0
C12—C7—C6	119.6 (2)
C13—N1—C1—C2	0.9 (4)	C9—C10—C11—C12	1.1 (4)
C13—N1—C1—Cl1	−179.99 (16)	C10—C11—C12—C7	−1.6 (4)
N1—C1—C2—C3	−0.6 (4)	C10—C11—C12—C13	177.6 (2)
Cl1—C1—C2—C3	−179.69 (17)	C8—C7—C12—C11	1.0 (3)
N1—C1—C2—C14	178.9 (2)	C6—C7—C12—C11	−179.3 (2)
Cl1—C1—C2—C14	−0.2 (3)	C8—C7—C12—C13	−178.2 (2)
C1—C2—C3—C4	−0.5 (3)	C6—C7—C12—C13	1.4 (3)
C14—C2—C3—C4	−180.0 (2)	C1—N1—C13—C4	−0.1 (3)
C2—C3—C4—C13	1.1 (3)	C1—N1—C13—C12	179.6 (2)
C2—C3—C4—C5	179.4 (2)	C3—C4—C13—N1	−0.8 (3)
C3—C4—C5—C6	−178.3 (2)	C5—C4—C13—N1	−179.2 (2)
C13—C4—C5—C6	0.0 (4)	C3—C4—C13—C12	179.5 (2)
C4—C5—C6—C7	−0.3 (4)	C5—C4—C13—C12	1.1 (3)
C5—C6—C7—C8	179.2 (2)	C11—C12—C13—N1	−0.7 (3)
C5—C6—C7—C12	−0.4 (4)	C7—C12—C13—N1	178.5 (2)
C12—C7—C8—C9	0.0 (4)	C11—C12—C13—C4	179.0 (2)
C6—C7—C8—C9	−179.6 (2)	C7—C12—C13—C4	−1.8 (3)
C7—C8—C9—C10	−0.6 (4)	C3—C2—C14—O1	10.7 (4)
C8—C9—C10—C11	0.0 (4)	C1—C2—C14—O1	−168.7 (3)