Quinoline-2-carbaldehyde.

The title compound, C(10)H(7)NO, crystallizes with two almost planar mol-ecules (A and B) in the asymmetric unit (r.m.s. deviations = 0.018 and 0.020 Å). In the crystal, the A mol-ecules are linked by weak C-H⋯O inter-actions, thereby generating C(9) [001] chains. The B mol-ecules do not exhibit any directional bonding inter-actions.

Related literature

For the synthesis of the title compound, see: Cooper & Cohen (1932 ▶). For its use in the synthesis of Schiff base ligands and imino-quinolyl-based transition metal complexes, see: Amandola & Mangano (2003 ▶); Prema & Wiznycia (2007 ▶); Ramos Silva et al. (2007 ▶); Ardizzoia et al. (2009 ▶). For its catalytic properties, see: Zhou et al. (2008 ▶).

Experimental

Crystal data

C10H7NO

M = 157.17

Monoclinic,

a = 7.0639 (7) Å

b = 21.564 (2) Å

c = 10.698 (1) Å

β = 107.884 (2)°

V = 1550.9 (3) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 173 K

0.16 × 0.09 × 0.06 mm

Data collection

Bruker Kappa DUO APEXII diffractometer

17618 measured reflections

3887 independent reflections

2379 reflections with I > 2σ(I)

R int = 0.055

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.117

S = 1.00

3887 reflections

217 parameters

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.23 e Å−3

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: SAINT (Bruker, 2006 ▶); 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 ▶); Atwood & Barbour, 2003 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811035653/hb6393sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811035653/hb6393Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811035653/hb6393Isup3.cml

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

C10H7NO	F(000) = 656
Mr = 157.17	Dx = 1.346 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 17618 reflections
a = 7.0639 (7) Å	θ = 2.2–28.4°
b = 21.564 (2) Å	µ = 0.09 mm−1
c = 10.698 (1) Å	T = 173 K
β = 107.884 (2)°	Needle, orange
V = 1550.9 (3) Å3	0.16 × 0.09 × 0.06 mm
Z = 8

Bruker Kappa DUO APEXII diffractometer	2379 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.055
graphite	θmax = 28.4°, θmin = 2.2°
0.5° φ scans and ω	h = −9→9
17618 measured reflections	k = −28→28
3887 independent reflections	l = −14→14

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.117	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0455P)2 + 0.3641P] where P = (Fo2 + 2Fc2)/3
3887 reflections	(Δ/σ)max < 0.001
217 parameters	Δρmax = 0.20 e Å−3
0 restraints	Δρmin = −0.23 e Å−3

Experimental. Half sphere of data collected using the Bruker SAINT software package. Crystal to detector distance = 45 mm; combination of φ and ω scans of 0.5°, 40 s per °, 2 iterations.

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.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) 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.

	x	y	z	Uiso*/Ueq
O1A	0.2759 (2)	0.51665 (7)	0.83374 (13)	0.0500 (4)
N1A	0.25666 (19)	0.46418 (6)	0.52163 (13)	0.0301 (3)
C1A	0.2419 (2)	0.48240 (7)	0.39656 (16)	0.0283 (4)
C2A	0.2385 (2)	0.43602 (8)	0.30235 (18)	0.0377 (4)
H2A	0.2458	0.3935	0.3265	0.045*
C3A	0.2247 (3)	0.45245 (10)	0.17677 (19)	0.0452 (5)
H3A	0.2207	0.4211	0.1137	0.054*
C4A	0.2162 (3)	0.51490 (10)	0.13944 (18)	0.0438 (5)
H4A	0.2089	0.5254	0.0518	0.053*
C5A	0.2184 (2)	0.56090 (9)	0.22770 (17)	0.0371 (4)
H5A	0.2126	0.6031	0.2013	0.045*
C6A	0.2292 (2)	0.54573 (7)	0.35861 (16)	0.0283 (4)
C7A	0.2265 (2)	0.59065 (8)	0.45389 (16)	0.0313 (4)
H7A	0.2169	0.6335	0.4319	0.038*
C8A	0.2379 (2)	0.57216 (7)	0.57762 (17)	0.0319 (4)
H8A	0.2340	0.6017	0.6427	0.038*
C9A	0.2557 (2)	0.50841 (8)	0.60734 (16)	0.0294 (4)
C10A	0.2734 (3)	0.48493 (9)	0.74045 (18)	0.0388 (4)
H10A	0.2836	0.4413	0.7534	0.047*
O1B	−0.60926 (19)	0.21792 (6)	0.27526 (14)	0.0513 (4)
N1B	−0.1295 (2)	0.27109 (6)	0.43627 (14)	0.0332 (3)
C1B	0.0608 (2)	0.25250 (7)	0.50026 (16)	0.0308 (4)
C2B	0.2086 (3)	0.29846 (8)	0.54640 (18)	0.0388 (4)
H2B	0.1752	0.3411	0.5320	0.047*
C3B	0.4002 (3)	0.28133 (9)	0.61193 (18)	0.0431 (5)
H3B	0.4990	0.3123	0.6430	0.052*
C4B	0.4520 (3)	0.21879 (9)	0.63369 (18)	0.0417 (4)
H4B	0.5860	0.2078	0.6786	0.050*
C5B	0.3129 (2)	0.17325 (9)	0.59128 (17)	0.0381 (4)
H5B	0.3501	0.1310	0.6076	0.046*
C6B	0.1131 (2)	0.18895 (8)	0.52288 (16)	0.0307 (4)
C7B	−0.0391 (2)	0.14417 (8)	0.47742 (17)	0.0341 (4)
H7B	−0.0098	0.1013	0.4913	0.041*
C8B	−0.2280 (2)	0.16321 (8)	0.41355 (17)	0.0343 (4)
H8B	−0.3323	0.1339	0.3821	0.041*
C9B	−0.2653 (2)	0.22733 (8)	0.39511 (16)	0.0311 (4)
C10B	−0.4680 (3)	0.25053 (9)	0.32446 (18)	0.0408 (4)
H10B	−0.4873	0.2941	0.3177	0.049*

	U11	U22	U33	U12	U13	U23
O1A	0.0461 (8)	0.0728 (10)	0.0322 (7)	−0.0039 (7)	0.0137 (6)	−0.0042 (7)
N1A	0.0271 (7)	0.0288 (7)	0.0334 (8)	−0.0013 (5)	0.0079 (6)	−0.0005 (6)
C1A	0.0212 (7)	0.0318 (9)	0.0314 (9)	−0.0018 (6)	0.0075 (6)	−0.0042 (7)
C2A	0.0332 (9)	0.0373 (10)	0.0425 (11)	−0.0025 (7)	0.0114 (8)	−0.0097 (8)
C3A	0.0361 (10)	0.0611 (13)	0.0397 (11)	−0.0047 (9)	0.0134 (8)	−0.0192 (9)
C4A	0.0320 (9)	0.0678 (14)	0.0311 (10)	−0.0047 (9)	0.0092 (7)	−0.0011 (9)
C5A	0.0290 (9)	0.0481 (11)	0.0340 (10)	−0.0020 (7)	0.0092 (7)	0.0042 (8)
C6A	0.0208 (7)	0.0331 (9)	0.0305 (9)	−0.0011 (6)	0.0073 (6)	0.0014 (7)
C7A	0.0295 (8)	0.0270 (8)	0.0373 (10)	−0.0005 (6)	0.0104 (7)	0.0017 (7)
C8A	0.0300 (8)	0.0306 (9)	0.0354 (10)	−0.0021 (7)	0.0105 (7)	−0.0063 (7)
C9A	0.0238 (8)	0.0341 (9)	0.0301 (9)	−0.0023 (6)	0.0079 (6)	−0.0011 (7)
C10A	0.0330 (9)	0.0471 (11)	0.0349 (10)	−0.0033 (8)	0.0085 (8)	0.0042 (8)
O1B	0.0357 (7)	0.0547 (9)	0.0539 (9)	0.0027 (6)	−0.0004 (6)	−0.0062 (7)
N1B	0.0370 (8)	0.0289 (7)	0.0336 (8)	0.0015 (6)	0.0107 (6)	−0.0016 (6)
C1B	0.0350 (9)	0.0304 (8)	0.0290 (9)	−0.0007 (7)	0.0129 (7)	−0.0026 (7)
C2B	0.0439 (10)	0.0333 (9)	0.0406 (10)	−0.0082 (8)	0.0148 (8)	−0.0047 (8)
C3B	0.0397 (10)	0.0475 (11)	0.0424 (11)	−0.0155 (8)	0.0131 (8)	−0.0071 (9)
C4B	0.0307 (9)	0.0530 (12)	0.0396 (10)	−0.0016 (8)	0.0081 (8)	−0.0013 (9)
C5B	0.0341 (9)	0.0399 (10)	0.0394 (10)	0.0017 (8)	0.0101 (8)	0.0023 (8)
C6B	0.0312 (8)	0.0321 (9)	0.0299 (9)	−0.0014 (7)	0.0110 (7)	−0.0001 (7)
C7B	0.0360 (9)	0.0257 (8)	0.0398 (10)	0.0009 (7)	0.0107 (8)	0.0010 (7)
C8B	0.0324 (9)	0.0306 (9)	0.0386 (10)	−0.0026 (7)	0.0091 (7)	−0.0036 (7)
C9B	0.0325 (8)	0.0310 (9)	0.0296 (9)	0.0025 (7)	0.0090 (7)	−0.0013 (7)
C10B	0.0404 (10)	0.0376 (10)	0.0413 (11)	0.0068 (8)	0.0080 (8)	0.0000 (8)

O1A—C10A	1.206 (2)	O1B—C10B	1.202 (2)
N1A—C9A	1.325 (2)	N1B—C9B	1.321 (2)
N1A—C1A	1.367 (2)	N1B—C1B	1.368 (2)
C1A—C2A	1.415 (2)	C1B—C2B	1.414 (2)
C1A—C6A	1.420 (2)	C1B—C6B	1.420 (2)
C2A—C3A	1.364 (3)	C2B—C3B	1.370 (3)
C2A—H2A	0.9500	C2B—H2B	0.9500
C3A—C4A	1.401 (3)	C3B—C4B	1.398 (3)
C3A—H3A	0.9500	C3B—H3B	0.9500
C4A—C5A	1.366 (3)	C4B—C5B	1.364 (2)
C4A—H4A	0.9500	C4B—H4B	0.9500
C5A—C6A	1.417 (2)	C5B—C6B	1.417 (2)
C5A—H5A	0.9500	C5B—H5B	0.9500
C6A—C7A	1.410 (2)	C6B—C7B	1.416 (2)
C7A—C8A	1.361 (2)	C7B—C8B	1.362 (2)
C7A—H7A	0.9500	C7B—H7B	0.9500
C8A—C9A	1.408 (2)	C8B—C9B	1.410 (2)
C8A—H8A	0.9500	C8B—H8B	0.9500
C9A—C10A	1.480 (2)	C9B—C10B	1.485 (2)
C10A—H10A	0.9500	C10B—H10B	0.9500
C9A—N1A—C1A	117.09 (14)	C9B—N1B—C1B	117.33 (14)
N1A—C1A—C2A	118.25 (15)	N1B—C1B—C2B	118.42 (15)
N1A—C1A—C6A	122.37 (14)	N1B—C1B—C6B	122.15 (14)
C2A—C1A—C6A	119.38 (15)	C2B—C1B—C6B	119.42 (15)
C3A—C2A—C1A	119.90 (17)	C3B—C2B—C1B	119.80 (17)
C3A—C2A—H2A	120.1	C3B—C2B—H2B	120.1
C1A—C2A—H2A	120.1	C1B—C2B—H2B	120.1
C2A—C3A—C4A	120.97 (18)	C2B—C3B—C4B	120.84 (17)
C2A—C3A—H3A	119.5	C2B—C3B—H3B	119.6
C4A—C3A—H3A	119.5	C4B—C3B—H3B	119.6
C5A—C4A—C3A	120.70 (18)	C5B—C4B—C3B	120.90 (17)
C5A—C4A—H4A	119.7	C5B—C4B—H4B	119.5
C3A—C4A—H4A	119.7	C3B—C4B—H4B	119.5
C4A—C5A—C6A	120.07 (17)	C4B—C5B—C6B	120.08 (17)
C4A—C5A—H5A	120.0	C4B—C5B—H5B	120.0
C6A—C5A—H5A	120.0	C6B—C5B—H5B	120.0
C7A—C6A—C5A	123.16 (16)	C7B—C6B—C5B	123.05 (15)
C7A—C6A—C1A	117.88 (15)	C7B—C6B—C1B	117.98 (15)
C5A—C6A—C1A	118.96 (15)	C5B—C6B—C1B	118.96 (15)
C8A—C7A—C6A	119.46 (15)	C8B—C7B—C6B	119.36 (15)
C8A—C7A—H7A	120.3	C8B—C7B—H7B	120.3
C6A—C7A—H7A	120.3	C6B—C7B—H7B	120.3
C7A—C8A—C9A	118.70 (15)	C7B—C8B—C9B	118.56 (15)
C7A—C8A—H8A	120.6	C7B—C8B—H8B	120.7
C9A—C8A—H8A	120.6	C9B—C8B—H8B	120.7
N1A—C9A—C8A	124.46 (15)	N1B—C9B—C8B	124.62 (15)
N1A—C9A—C10A	113.76 (15)	N1B—C9B—C10B	114.65 (15)
C8A—C9A—C10A	121.78 (15)	C8B—C9B—C10B	120.73 (15)
O1A—C10A—C9A	125.30 (18)	O1B—C10B—C9B	124.52 (17)
O1A—C10A—H10A	117.4	O1B—C10B—H10B	117.7
C9A—C10A—H10A	117.4	C9B—C10B—H10B	117.7
C9A—N1A—C1A—C2A	−178.72 (14)	C9B—N1B—C1B—C2B	−179.40 (16)
C9A—N1A—C1A—C6A	1.0 (2)	C9B—N1B—C1B—C6B	−0.2 (2)
N1A—C1A—C2A—C3A	−179.74 (15)	N1B—C1B—C2B—C3B	179.39 (16)
C6A—C1A—C2A—C3A	0.5 (2)	C6B—C1B—C2B—C3B	0.2 (3)
C1A—C2A—C3A—C4A	0.8 (3)	C1B—C2B—C3B—C4B	0.2 (3)
C2A—C3A—C4A—C5A	−1.1 (3)	C2B—C3B—C4B—C5B	−0.6 (3)
C3A—C4A—C5A—C6A	0.0 (3)	C3B—C4B—C5B—C6B	0.7 (3)
C4A—C5A—C6A—C7A	−178.22 (16)	C4B—C5B—C6B—C7B	−179.28 (17)
C4A—C5A—C6A—C1A	1.3 (2)	C4B—C5B—C6B—C1B	−0.4 (3)
N1A—C1A—C6A—C7A	−1.7 (2)	N1B—C1B—C6B—C7B	−0.3 (2)
C2A—C1A—C6A—C7A	178.00 (15)	C2B—C1B—C6B—C7B	178.91 (16)
N1A—C1A—C6A—C5A	178.70 (14)	N1B—C1B—C6B—C5B	−179.26 (15)
C2A—C1A—C6A—C5A	−1.6 (2)	C2B—C1B—C6B—C5B	−0.1 (2)
C5A—C6A—C7A—C8A	−179.86 (15)	C5B—C6B—C7B—C8B	179.36 (17)
C1A—C6A—C7A—C8A	0.6 (2)	C1B—C6B—C7B—C8B	0.4 (2)
C6A—C7A—C8A—C9A	1.1 (2)	C6B—C7B—C8B—C9B	−0.1 (3)
C1A—N1A—C9A—C8A	0.9 (2)	C1B—N1B—C9B—C8B	0.6 (3)
C1A—N1A—C9A—C10A	−179.66 (13)	C1B—N1B—C9B—C10B	−179.01 (15)
C7A—C8A—C9A—N1A	−2.0 (2)	C7B—C8B—C9B—N1B	−0.4 (3)
C7A—C8A—C9A—C10A	178.60 (15)	C7B—C8B—C9B—C10B	179.14 (16)
N1A—C9A—C10A—O1A	179.95 (16)	N1B—C9B—C10B—O1B	176.94 (18)
C8A—C9A—C10A—O1A	−0.6 (3)	C8B—C9B—C10B—O1B	−2.6 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C4A—H4A···O1Ai	0.95	2.53	3.424 (2)	158

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4A—H4A⋯O1Ai	0.95	2.53	3.424 (2)	158

Symmetry code: (i) .