(E)-2-[2-(3-Fluoro­phen­yl)ethen­yl]quinolin-8-yl acetate

Huo, Y.-P.; Nie, X.-L.; Fang, X.-M.

doi:10.1107/S1600536812030255

organic compounds

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ISSN: 2056-9890

Volume 68| Part 8| August 2012| Page o2420

https://doi.org/10.1107/S1600536812030255

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(E)-2-[2-(3-Fluorophenyl)ethenyl]quinolin-8-yl acetate

Yan-Ping Huo,^a ^* Xiao-Li Nie ^a and Xiao-Ming Fang ^a

^aSchool of Chemical Engineering and Light Industry, Guangdong University of Technology, Guangzhou 510006, People's Republic of China
^*Correspondence e-mail: tigerhuo1974@yahoo.com.cn

(Received 14 May 2012; accepted 3 July 2012; online 10 July 2012)

In the crystal of the title compound, C₁₉H₁₄FNO₂, the molecules are linked by C—H⋯O hydrogen bonds in translational chains along the b axis. The dihedral angles formed by the quinoline system with the fluorobenzene ring and the acetoxy group are 8.15 (3) and 77.42 (4)°, respectively.

Related literature

For the synthetic procedure, see: Zeng et al. (2006 ).

Experimental

Crystal data

C₁₉H₁₄FNO₂
M_r = 307.31
Monoclinic, P 2₁ /c
a = 17.628 (3) Å
b = 5.2641 (9) Å
c = 16.062 (3) Å
β = 100.528 (2)°
V = 1465.4 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 110 K
0.35 × 0.24 × 0.18 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.972, T_max = 0.982
8139 measured reflections
3177 independent reflections
2663 reflections with I > 2σ(I)
R_int = 0.017

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.134
S = 1.02
3177 reflections
208 parameters
H-atom parameters constrained
Δρ_max = 0.67 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1D⋯O2ⁱ	0.98 (1)	2.54 (1)	3.495 (2)	166 (2)
Symmetry code: (i) x, y+1, z.

Data collection: SMART (Bruker, 2008 ); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536812030255/ld2060sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812030255/ld2060Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812030255/ld2060Isup3.cdx

Supporting information file. DOI: https://doi.org/10.1107/S1600536812030255/ld2060Isup4.cml

checkCIF report

Comment top

The (E)-2-[2-(3-fluorophenyl)ethenyl]-8-acetoxyquinoline was prepared via a reaction of 2-methyl-8-hydroxyquinaldine with 3-fluorobenzaldehyde according to Zeng et al. (2006). The molecular structure is shown on Fig. 1. There are non- classical intermolecular hydrogen bonds C–H···O between carbonyl oxygen and the methyl group (C···O = 3.495 (2) Å; C–H···O = 166°) connecting molecules into chains along the b axis.

Related literature top

For the synthetic procedure, see: Zeng et al. (2006).

Experimental top

The title compound was prepared by a method reported in the literature, see: Zeng et al. (2006). The crystals were obtained by dissolving the compound (0.1 g) in dichloromethane (5 ml) and then evaporating the solvent slowly at room temperature for about 3 days.

Structure description top

For the synthetic procedure, see: Zeng et al. (2006).

Computing details top

Data collection: SMART [or APEX2?] (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The asymmetric unit of the title compound.

(E)-2-[2-(3-Fluorophenyl)ethenyl]quinolin-8-yl acetate top

Crystal data top

C₁₉H₁₄FNO₂	F(000) = 640
M_r = 307.31	D_x = 1.393 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 8139 reflections
a = 17.628 (3) Å	θ = 2.4–27.1°
b = 5.2641 (9) Å	µ = 0.10 mm⁻¹
c = 16.062 (3) Å	T = 110 K
β = 100.528 (2)°	Plate, colorless
V = 1465.4 (4) Å³	0.35 × 0.24 × 0.18 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	3177 independent reflections
Radiation source: fine-focus sealed tube	2663 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.017
φ and ω scans	θ_max = 27.1°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −22→22
T_min = 0.972, T_max = 0.982	k = −6→6
8139 measured reflections	l = −20→16

Refinement top

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.134	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0792P)² + 0.6625P] where P = (F_o² + 2F_c²)/3
3177 reflections	(Δ/σ)_max < 0.001
208 parameters	Δρ_max = 0.67 e Å⁻³
0 restraints	Δρ_min = −0.26 e Å⁻³

Crystal data top

C₁₉H₁₄FNO₂	V = 1465.4 (4) Å³
M_r = 307.31	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 17.628 (3) Å	µ = 0.10 mm⁻¹
b = 5.2641 (9) Å	T = 110 K
c = 16.062 (3) Å	0.35 × 0.24 × 0.18 mm
β = 100.528 (2)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	3177 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2663 reflections with I > 2σ(I)
T_min = 0.972, T_max = 0.982	R_int = 0.017
8139 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.134	H-atom parameters constrained
S = 1.02	Δρ_max = 0.67 e Å⁻³
3177 reflections	Δρ_min = −0.26 e Å⁻³
208 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	0.34904 (6)	0.31492 (19)	0.74280 (6)	0.0242 (2)
N1	0.26746 (7)	−0.0961 (2)	0.66528 (7)	0.0220 (3)
F1	−0.13987 (6)	−0.95702 (19)	0.54984 (6)	0.0398 (3)
O2	0.36690 (7)	0.0337 (2)	0.85047 (7)	0.0308 (3)
C9	0.22819 (8)	−0.2876 (3)	0.62482 (8)	0.0225 (3)
C8	0.34042 (8)	−0.0532 (3)	0.65088 (8)	0.0213 (3)
C19	−0.02215 (9)	−0.7381 (3)	0.58416 (9)	0.0279 (3)
H19A	0.0009	−0.8581	0.5523	0.033*
C7	0.37520 (8)	−0.2014 (3)	0.59403 (8)	0.0225 (3)
C14	0.02131 (8)	−0.5360 (3)	0.62403 (9)	0.0236 (3)
C17	−0.13480 (8)	−0.5983 (3)	0.63768 (9)	0.0279 (3)
H17A	−0.1874	−0.6201	0.6420	0.033*
C3	0.38386 (8)	0.1525 (3)	0.69226 (8)	0.0224 (3)
C12	0.14966 (8)	−0.3207 (3)	0.64139 (9)	0.0239 (3)
H12A	0.1314	−0.1968	0.6760	0.029*
C11	0.33106 (8)	−0.4031 (3)	0.55183 (8)	0.0248 (3)
H11A	0.3517	−0.5070	0.5131	0.030*
C4	0.45559 (8)	0.2107 (3)	0.67758 (9)	0.0254 (3)
H4A	0.4828	0.3519	0.7053	0.031*
C6	0.45038 (8)	−0.1410 (3)	0.58087 (9)	0.0263 (3)
H6A	0.4739	−0.2420	0.5436	0.032*
C5	0.48937 (8)	0.0617 (3)	0.62139 (9)	0.0277 (3)
H5A	0.5395	0.1021	0.6116	0.033*
C10	0.25884 (8)	−0.4474 (3)	0.56703 (9)	0.0248 (3)
H10A	0.2289	−0.5835	0.5394	0.030*
C16	−0.09130 (8)	−0.3979 (3)	0.67832 (9)	0.0279 (3)
H16A	−0.1146	−0.2810	0.7110	0.033*
C18	−0.09877 (9)	−0.7629 (3)	0.59126 (9)	0.0275 (3)
C15	−0.01447 (8)	−0.3665 (3)	0.67175 (9)	0.0252 (3)
H15A	0.0141	−0.2287	0.6999	0.030*
C13	0.10159 (8)	−0.5092 (3)	0.61214 (9)	0.0262 (3)
H13A	0.1211	−0.6386	0.5806	0.031*
C2	0.34043 (8)	0.2298 (3)	0.82022 (9)	0.0241 (3)
C1	0.29471 (9)	0.4184 (3)	0.86069 (11)	0.0334 (4)
H1B	0.2887	0.3564	0.9166	0.050*
H1C	0.2437	0.4403	0.8251	0.050*
H1D	0.3218	0.5818	0.8668	0.050*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0275 (5)	0.0202 (5)	0.0253 (5)	0.0016 (4)	0.0058 (4)	−0.0001 (4)
N1	0.0229 (6)	0.0225 (6)	0.0209 (6)	0.0027 (4)	0.0049 (4)	0.0021 (4)
F1	0.0423 (6)	0.0331 (5)	0.0408 (6)	−0.0137 (4)	−0.0008 (4)	−0.0013 (4)
O2	0.0405 (6)	0.0254 (6)	0.0286 (5)	0.0033 (5)	0.0118 (5)	0.0030 (4)
C9	0.0236 (6)	0.0245 (7)	0.0190 (6)	0.0022 (5)	0.0028 (5)	0.0035 (5)
C8	0.0225 (6)	0.0221 (7)	0.0192 (6)	0.0030 (5)	0.0039 (5)	0.0043 (5)
C19	0.0344 (8)	0.0259 (7)	0.0238 (7)	−0.0037 (6)	0.0065 (6)	−0.0017 (6)
C7	0.0245 (7)	0.0250 (7)	0.0183 (6)	0.0044 (5)	0.0044 (5)	0.0046 (5)
C14	0.0273 (7)	0.0232 (7)	0.0198 (6)	−0.0022 (5)	0.0029 (5)	0.0034 (5)
C17	0.0227 (7)	0.0292 (8)	0.0302 (7)	−0.0035 (6)	0.0007 (6)	0.0087 (6)
C3	0.0254 (7)	0.0213 (7)	0.0207 (6)	0.0044 (5)	0.0050 (5)	0.0031 (5)
C12	0.0245 (7)	0.0261 (7)	0.0213 (6)	0.0015 (6)	0.0050 (5)	0.0006 (5)
C11	0.0297 (7)	0.0269 (7)	0.0184 (6)	0.0051 (6)	0.0061 (5)	−0.0002 (5)
C4	0.0250 (7)	0.0252 (7)	0.0253 (7)	−0.0018 (5)	0.0025 (5)	0.0044 (5)
C6	0.0266 (7)	0.0313 (8)	0.0227 (7)	0.0052 (6)	0.0089 (5)	0.0040 (6)
C5	0.0232 (7)	0.0348 (8)	0.0259 (7)	0.0002 (6)	0.0065 (6)	0.0070 (6)
C10	0.0275 (7)	0.0252 (7)	0.0208 (6)	0.0009 (6)	0.0017 (5)	−0.0011 (5)
C16	0.0265 (7)	0.0267 (8)	0.0301 (7)	0.0028 (6)	0.0042 (6)	0.0021 (6)
C18	0.0319 (7)	0.0233 (7)	0.0244 (7)	−0.0082 (6)	−0.0025 (6)	0.0044 (5)
C15	0.0256 (7)	0.0220 (7)	0.0266 (7)	−0.0016 (5)	0.0015 (6)	0.0011 (5)
C13	0.0288 (7)	0.0260 (7)	0.0245 (7)	−0.0007 (6)	0.0070 (6)	−0.0008 (5)
C2	0.0239 (6)	0.0222 (7)	0.0272 (7)	−0.0039 (5)	0.0070 (5)	−0.0016 (5)
C1	0.0351 (8)	0.0267 (8)	0.0424 (9)	0.0000 (6)	0.0177 (7)	−0.0047 (7)

Geometric parameters (Å, º) top

O1—C2	1.3561 (17)	C3—C4	1.3627 (19)
O1—C3	1.3962 (17)	C12—C13	1.334 (2)
N1—C9	1.3241 (19)	C12—H12A	0.9500
N1—C8	1.3667 (17)	C11—C10	1.360 (2)
F1—C18	1.3550 (17)	C11—H11A	0.9500
O2—C2	1.1986 (18)	C4—C5	1.407 (2)
C9—C10	1.430 (2)	C4—H4A	0.9500
C9—C12	1.4669 (19)	C6—C5	1.368 (2)
C8—C3	1.419 (2)	C6—H6A	0.9500
C8—C7	1.4221 (19)	C5—H5A	0.9500
C19—C18	1.382 (2)	C10—H10A	0.9500
C19—C14	1.396 (2)	C16—C15	1.387 (2)
C19—H19A	0.9500	C16—H16A	0.9500
C7—C11	1.414 (2)	C15—H15A	0.9500
C7—C6	1.4157 (19)	C13—H13A	0.9500
C14—C15	1.399 (2)	C2—C1	1.500 (2)
C14—C13	1.469 (2)	C1—H1B	0.9800
C17—C18	1.372 (2)	C1—H1C	0.9800
C17—C16	1.394 (2)	C1—H1D	0.9800
C17—H17A	0.9500

C2—O1—C3	117.75 (11)	C5—C4—H4A	120.0
C9—N1—C8	117.80 (12)	C5—C6—C7	120.43 (13)
N1—C9—C10	122.74 (13)	C5—C6—H6A	119.8
N1—C9—C12	115.29 (12)	C7—C6—H6A	119.8
C10—C9—C12	121.95 (13)	C6—C5—C4	120.35 (13)
N1—C8—C3	119.39 (12)	C6—C5—H5A	119.8
N1—C8—C7	123.20 (13)	C4—C5—H5A	119.8
C3—C8—C7	117.39 (12)	C11—C10—C9	119.54 (13)
C18—C19—C14	119.78 (14)	C11—C10—H10A	120.2
C18—C19—H19A	120.1	C9—C10—H10A	120.2
C14—C19—H19A	120.1	C15—C16—C17	121.03 (14)
C11—C7—C6	123.02 (13)	C15—C16—H16A	119.5
C11—C7—C8	117.10 (12)	C17—C16—H16A	119.5
C6—C7—C8	119.87 (13)	F1—C18—C17	118.95 (14)
C19—C14—C15	118.19 (13)	F1—C18—C19	118.26 (14)
C19—C14—C13	118.33 (13)	C17—C18—C19	122.79 (14)
C15—C14—C13	123.46 (13)	C16—C15—C14	120.65 (14)
C18—C17—C16	117.54 (14)	C16—C15—H15A	119.7
C18—C17—H17A	121.2	C14—C15—H15A	119.7
C16—C17—H17A	121.2	C12—C13—C14	126.22 (14)
C4—C3—O1	118.91 (13)	C12—C13—H13A	116.9
C4—C3—C8	121.92 (13)	C14—C13—H13A	116.9
O1—C3—C8	118.86 (12)	O2—C2—O1	123.76 (13)
C13—C12—C9	125.75 (14)	O2—C2—C1	126.49 (14)
C13—C12—H12A	117.1	O1—C2—C1	109.74 (12)
C9—C12—H12A	117.1	C2—C1—H1B	109.5
C10—C11—C7	119.61 (13)	C2—C1—H1C	109.5
C10—C11—H11A	120.2	H1B—C1—H1C	109.5
C7—C11—H11A	120.2	C2—C1—H1D	109.5
C3—C4—C5	120.02 (14)	H1B—C1—H1D	109.5
C3—C4—H4A	120.0	H1C—C1—H1D	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1D···O2ⁱ	0.98 (1)	2.54 (1)	3.495 (2)	166 (2)

Symmetry code: (i) x, y+1, z.

Experimental details

Crystal data
Chemical formula	C₁₉H₁₄FNO₂
M_r	307.31
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	110
a, b, c (Å)	17.628 (3), 5.2641 (9), 16.062 (3)
β (°)	100.528 (2)
V (Å³)	1465.4 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.35 × 0.24 × 0.18

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.972, 0.982
No. of measured, independent and observed [I > 2σ(I)] reflections	8139, 3177, 2663
R_int	0.017
(sin θ/λ)_max (Å⁻¹)	0.641

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.134, 1.02
No. of reflections	3177
No. of parameters	208
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.67, −0.26

Computer programs: SMART [or APEX2?] (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1D···O2ⁱ	0.98 (0)	2.54 (0)	3.495 (2)	166 (2)

Symmetry code: (i) x, y+1, z.

Acknowledgements

This work was supported by the National Natural Science Foundation of China (grant Nos. 20802010 and 21172047) and the 211 project of Guangdong Province.

References

Bruker (2008). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zeng, H., OuYang, X., Wang, T., Yuan, G., Zhang, G. & Zhang, X. (2006). Cryst. Growth Des. 6, 1697–1702. Web of Science CSD CrossRef CAS Google Scholar