2-Formyl­quinolin-8-yl acetate

Wang, W.-H.; You, Z.-L.; Li, X.-F.; Liu, W.-S.

doi:10.1107/S1600536805039322

2-Formylquinolin-8-yl acetate

W.-H. Wang, Z.-L. You, X.-F. Li and W.-S. Liu

In the crystal structure of the title compound, C₁₂H₉NO₃, the molecules are linked through weak intermolecular C—H

O hydrogen bonds, forming a two-dimensional network.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805039322/lh6544sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536805039322/lh6544Isup2.hkl Contains datablock I

CCDC reference: 296604

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Key indicators

Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.003 Å
R factor = 0.044
wR factor = 0.134
Data-to-parameter ratio = 15.7

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Comment top

The title compound, (I), is a derivative of pyridylaldehyde, which readily forms Schiff base compounds by condensation with amines.

In (I), all the bond lengths are within normal ranges (Allen et al., 1987). The dihedral angle between the plane of atoms O2/C11/O3 and the quinoline ring is 82.9 (2)° (Fig. 1). The conformation of the acetoxy group is desecribed by the torsion angle of −169.42 (17)° for C9—O2—C11—C12.

In the crystal structure, molecules are linked via weak intermolecular C—H···O hydrogen bonds to form a two-dimensional sheet perpendicular to the c axis (Table 1).

Experimental top

One drop of concentrated sulfuric acid was added to a mixture of 2-methyl-8-hydroxyquinoline (15.9 g, 0.1 mol) and acetic anhydride (10.2 g, 9.4 ml, 0.1 mol) in a 250 ml Erlenmeyer flask. The mixture was warmed rapidly and stirred gently by hand. After 5 min, the clear solution was poured onto crushed ice (about 200 ml). The solid was filtered off and washed with water (200 ml). The compound obtained was 2-methyl-8-acetoxyquionoline (18.6 g, 93%; m.p. 394–395 K). To a dioxane supension (40 ml) of freshly sublimed selenium dioxide (5.8 g), a dioxane solution (50 ml) of 2-methyl-8-acetoxyquionoline (11.4 g) was added with stirring over a water bath at 323–328 K for 3 h. The mixture was filtered after being allowed to stand for 2 h. The dioxane was distilled off to give light-yellow [Colourless below?] crystals of (I) (9.0 g; m.p. 367–368 K).

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

Figures top

Fig. 1. The structure of (I). Displacement ellipsoids are drawn at the 30% probability level.

2-Formylquinolin-8-yl acetate top

Crystal data top

C₁₂H₉NO₃	F(000) = 896
M_r = 215.20	D_x = 1.341 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 3212 reflections
a = 19.743 (3) Å	θ = 2.3–24.9°
b = 7.863 (1) Å	µ = 0.10 mm⁻¹
c = 14.771 (2) Å	T = 298 K
β = 111.66 (2)°	Block, colourless
V = 2131.1 (6) Å³	0.53 × 0.46 × 0.41 mm
Z = 8

Data collection top

Bruker SMART CCD area-detector diffractometer	2315 independent reflections
Radiation source: fine-focus sealed tube	1225 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.045
ω scans	θ_max = 27.0°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −24→25
T_min = 0.950, T_max = 0.961	k = −8→10
6309 measured reflections	l = −18→18

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.044	H-atom parameters constrained
wR(F²) = 0.134	w = 1/[σ²(F_o²) + (0.0577P)² + 0.2105P] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max < 0.001
2315 reflections	Δρ_max = 0.18 e Å⁻³
147 parameters	Δρ_min = −0.15 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997a), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0073 (10)

Crystal data top

C₁₂H₉NO₃	V = 2131.1 (6) Å³
M_r = 215.20	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 19.743 (3) Å	µ = 0.10 mm⁻¹
b = 7.863 (1) Å	T = 298 K
c = 14.771 (2) Å	0.53 × 0.46 × 0.41 mm
β = 111.66 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	2315 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1225 reflections with I > 2σ(I)
T_min = 0.950, T_max = 0.961	R_int = 0.045
6309 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.134	H-atom parameters constrained
S = 1.00	Δρ_max = 0.18 e Å⁻³
2315 reflections	Δρ_min = −0.15 e Å⁻³
147 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.49901 (9)	0.3345 (2)	0.06274 (13)	0.0936 (6)
O2	0.36311 (8)	0.76088 (17)	0.29079 (10)	0.0607 (4)
O3	0.38384 (8)	0.98008 (19)	0.20739 (11)	0.0740 (5)
N1	0.38935 (8)	0.57120 (19)	0.15299 (11)	0.0504 (4)
C1	0.47836 (12)	0.4333 (3)	0.10849 (17)	0.0664 (6)
H1	0.5132	0.4880	0.1609	0.080*
C2	0.40071 (11)	0.4739 (2)	0.08687 (14)	0.0517 (5)
C3	0.34551 (12)	0.4121 (3)	0.00338 (15)	0.0591 (6)
H3	0.3567	0.3458	−0.0413	0.071*
C4	0.27550 (12)	0.4505 (2)	−0.01135 (15)	0.0594 (6)
H4	0.2381	0.4111	−0.0667	0.071*
C5	0.25934 (10)	0.5498 (2)	0.05699 (15)	0.0513 (5)
C6	0.18791 (11)	0.5936 (3)	0.04871 (18)	0.0648 (6)
H6	0.1483	0.5557	−0.0045	0.078*
C7	0.17674 (12)	0.6905 (3)	0.1177 (2)	0.0730 (7)
H7	0.1294	0.7187	0.1111	0.088*
C8	0.23503 (13)	0.7488 (3)	0.19863 (18)	0.0671 (6)
H8	0.2263	0.8141	0.2457	0.080*
C9	0.30466 (11)	0.7102 (2)	0.20868 (15)	0.0528 (5)
C10	0.31877 (10)	0.6083 (2)	0.13869 (13)	0.0468 (5)
C11	0.40329 (12)	0.8948 (3)	0.27912 (16)	0.0572 (6)
C12	0.47099 (13)	0.9152 (3)	0.36568 (15)	0.0743 (7)
H12A	0.5071	0.8365	0.3619	0.111*
H12B	0.4611	0.8929	0.4235	0.111*
H12C	0.4888	1.0293	0.3678	0.111*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0852 (13)	0.0961 (13)	0.1035 (14)	0.0277 (10)	0.0395 (11)	−0.0138 (10)
O2	0.0672 (10)	0.0644 (9)	0.0526 (9)	−0.0017 (7)	0.0246 (8)	−0.0006 (7)
O3	0.0743 (11)	0.0739 (11)	0.0673 (11)	−0.0068 (8)	0.0186 (9)	0.0131 (8)
N1	0.0443 (10)	0.0531 (10)	0.0511 (10)	0.0015 (7)	0.0147 (8)	0.0025 (8)
C1	0.0580 (15)	0.0665 (15)	0.0733 (15)	0.0114 (11)	0.0225 (12)	0.0016 (12)
C2	0.0508 (13)	0.0491 (11)	0.0527 (12)	0.0019 (9)	0.0164 (10)	0.0023 (9)
C3	0.0634 (15)	0.0534 (13)	0.0559 (13)	0.0000 (10)	0.0168 (12)	−0.0042 (10)
C4	0.0612 (15)	0.0496 (12)	0.0546 (13)	−0.0122 (10)	0.0063 (11)	0.0025 (10)
C5	0.0454 (12)	0.0460 (11)	0.0579 (13)	−0.0049 (9)	0.0135 (10)	0.0122 (10)
C6	0.0443 (13)	0.0617 (14)	0.0809 (16)	−0.0055 (10)	0.0142 (12)	0.0163 (12)
C7	0.0474 (14)	0.0717 (16)	0.105 (2)	0.0042 (11)	0.0343 (15)	0.0234 (14)
C8	0.0661 (16)	0.0646 (14)	0.0817 (17)	0.0057 (11)	0.0403 (14)	0.0078 (12)
C9	0.0515 (13)	0.0543 (12)	0.0555 (13)	0.0004 (10)	0.0232 (11)	0.0066 (10)
C10	0.0414 (12)	0.0456 (11)	0.0517 (12)	−0.0006 (8)	0.0154 (10)	0.0095 (9)
C11	0.0588 (14)	0.0595 (14)	0.0567 (14)	0.0069 (11)	0.0254 (12)	−0.0056 (11)
C12	0.0698 (16)	0.0783 (17)	0.0658 (15)	−0.0018 (12)	0.0147 (13)	−0.0051 (12)

Geometric parameters (Å, º) top

O1—C1	1.195 (2)	C5—C6	1.412 (3)
O2—C11	1.367 (2)	C5—C10	1.414 (3)
O2—C9	1.389 (2)	C6—C7	1.354 (3)
O3—C11	1.191 (2)	C6—H6	0.9300
N1—C2	1.324 (2)	C7—C8	1.396 (3)
N1—C10	1.362 (2)	C7—H7	0.9300
C1—C2	1.481 (3)	C8—C9	1.361 (3)
C1—H1	0.9300	C8—H8	0.9300
C2—C3	1.397 (3)	C9—C10	1.415 (3)
C3—C4	1.352 (3)	C11—C12	1.478 (3)
C3—H3	0.9300	C12—H12A	0.9600
C4—C5	1.403 (3)	C12—H12B	0.9600
C4—H4	0.9300	C12—H12C	0.9600

C11—O2—C9	116.42 (15)	C6—C7—H7	119.4
C2—N1—C10	116.86 (16)	C8—C7—H7	119.4
O1—C1—C2	124.1 (2)	C9—C8—C7	120.0 (2)
O1—C1—H1	118.0	C9—C8—H8	120.0
C2—C1—H1	118.0	C7—C8—H8	120.0
N1—C2—C3	124.25 (18)	C8—C9—O2	120.7 (2)
N1—C2—C1	114.17 (18)	C8—C9—C10	120.7 (2)
C3—C2—C1	121.6 (2)	O2—C9—C10	118.47 (17)
C4—C3—C2	118.9 (2)	N1—C10—C5	122.84 (18)
C4—C3—H3	120.6	N1—C10—C9	118.31 (17)
C2—C3—H3	120.6	C5—C10—C9	118.86 (18)
C3—C4—C5	119.94 (19)	O3—C11—O2	122.3 (2)
C3—C4—H4	120.0	O3—C11—C12	126.9 (2)
C5—C4—H4	120.0	O2—C11—C12	110.85 (19)
C4—C5—C6	123.9 (2)	C11—C12—H12A	109.5
C4—C5—C10	117.23 (18)	C11—C12—H12B	109.5
C6—C5—C10	118.8 (2)	H12A—C12—H12B	109.5
C7—C6—C5	120.5 (2)	C11—C12—H12C	109.5
C7—C6—H6	119.8	H12A—C12—H12C	109.5
C5—C6—H6	119.8	H12B—C12—H12C	109.5
C6—C7—C8	121.2 (2)

C10—N1—C2—C3	1.8 (3)	C11—O2—C9—C8	−104.8 (2)
C10—N1—C2—C1	−177.92 (16)	C11—O2—C9—C10	79.2 (2)
O1—C1—C2—N1	172.6 (2)	C2—N1—C10—C5	−1.0 (3)
O1—C1—C2—C3	−7.2 (3)	C2—N1—C10—C9	179.17 (16)
N1—C2—C3—C4	−1.2 (3)	C4—C5—C10—N1	−0.4 (3)
C1—C2—C3—C4	178.58 (18)	C6—C5—C10—N1	179.49 (16)
C2—C3—C4—C5	−0.4 (3)	C4—C5—C10—C9	179.40 (16)
C3—C4—C5—C6	−178.78 (18)	C6—C5—C10—C9	−0.7 (3)
C3—C4—C5—C10	1.1 (3)	C8—C9—C10—N1	−178.98 (17)
C4—C5—C6—C7	−179.8 (2)	O2—C9—C10—N1	−2.9 (3)
C10—C5—C6—C7	0.3 (3)	C8—C9—C10—C5	1.2 (3)
C5—C6—C7—C8	−0.3 (3)	O2—C9—C10—C5	177.26 (15)
C6—C7—C8—C9	0.8 (3)	C9—O2—C11—O3	10.7 (3)
C7—C8—C9—O2	−177.19 (17)	C9—O2—C11—C12	−169.42 (17)
C7—C8—C9—C10	−1.2 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O1ⁱ	0.93	2.57	3.486 (3)	168
C12—H12C···O1ⁱⁱ	0.96	2.59	3.447 (3)	149

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

Experimental details

Crystal data
Chemical formula	C₁₂H₉NO₃
M_r	215.20
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	298
a, b, c (Å)	19.743 (3), 7.863 (1), 14.771 (2)
β (°)	111.66 (2)
V (Å³)	2131.1 (6)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.53 × 0.46 × 0.41

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.950, 0.961
No. of measured, independent and observed [I > 2σ(I)] reflections	6309, 2315, 1225
R_int	0.045
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.134, 1.00
No. of reflections	2315
No. of parameters	147
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.15

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SAINT, SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b), SHELXTL.