(2E)-3-(Dimethyl-amino)-1-(4-fluoro-phen-yl)prop-2-en-1-one.

In the title compound, C(11)H(12)FNO, the dihedral angle between the prop-2-en-1-one group and the benzene ring is 19.33 (6)°. The configuration of the keto group with respect to the olefinic double bond is s-cis. In the crystal, the mol-ecules form dimers through aromatic π-π stacking inter-actions [centroid-centroid distance = 3.667 (1) Å] and are linked via C-H⋯O inter-actions into chains along the b axis.

Related literature

For the synthesis and pharmaceutical activity of enamino­nes, see: Kantevari et al. (2007 ▶); Ke et al. (2009 ▶); Omran et al. (1997 ▶); Eddington et al. (2003 ▶). For a related structure, see: Deng et al. (2010 ▶).

Experimental

Crystal data

C11H12FNO

M = 193.22

Monoclinic,

a = 13.2832 (6) Å

b = 5.8530 (2) Å

c = 14.2995 (8) Å

β = 116.086 (6)°

V = 998.49 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 293 K

0.3 × 0.2 × 0.2 mm

Data collection

Oxford Diffraction Xcalibur Sapphire3 diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 ▶) T min = 0.824, T max = 1.000

14183 measured reflections

1952 independent reflections

1430 reflections with I > 2σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.133

S = 1.04

1952 reflections

129 parameters

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.16 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); 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: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S160053681204202X/gk2520sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681204202X/gk2520Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S160053681204202X/gk2520Isup3.cml

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

C11H12FNO	F(000) = 408
Mr = 193.22	Dx = 1.285 Mg m−3
Monoclinic, P21/c	Melting point = 336–335 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 13.2832 (6) Å	Cell parameters from 5766 reflections
b = 5.8530 (2) Å	θ = 3.5–29.0°
c = 14.2995 (8) Å	µ = 0.10 mm−1
β = 116.086 (6)°	T = 293 K
V = 998.49 (8) Å3	Block, yellow
Z = 4	0.3 × 0.2 × 0.2 mm

Oxford Diffraction Xcalibur Sapphire3 diffractometer	1952 independent reflections
Radiation source: fine-focus sealed tube	1430 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.040
Detector resolution: 16.1049 pixels mm-1	θmax = 26.0°, θmin = 3.5°
ω scan	h = −16→16
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	k = −7→7
Tmin = 0.824, Tmax = 1.000	l = −17→17
14183 measured reflections

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.133	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0668P)2 + 0.1767P] where P = (Fo2 + 2Fc2)/3
1952 reflections	(Δ/σ)max = 0.002
129 parameters	Δρmax = 0.20 e Å−3
0 restraints	Δρmin = −0.16 e Å−3

Experimental. CrysAlis PRO, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27–08-2010 CrysAlis171. NET) (compiled Aug 27 2010,11:50:40) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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
C7	0.14077 (14)	0.3879 (3)	0.44568 (12)	0.0387 (4)
F1	−0.19144 (9)	0.5459 (2)	0.27506 (10)	0.0802 (4)
O1	0.28148 (11)	0.1122 (2)	0.52645 (12)	0.0752 (5)
C1	0.26094 (15)	0.3183 (3)	0.50936 (13)	0.0463 (4)
C2	0.34503 (14)	0.4916 (3)	0.54818 (13)	0.0457 (4)
H2	0.3259	0.6447	0.5332	0.055*
C3	0.45299 (14)	0.4299 (3)	0.60714 (13)	0.0489 (5)
H3	0.4653	0.2738	0.6186	0.059*
N4	0.54383 (12)	0.5600 (2)	0.65100 (12)	0.0548 (5)
C5	0.53933 (17)	0.8047 (3)	0.63606 (18)	0.0656 (6)
H5A	0.5800	0.8453	0.5972	0.098*
H5B	0.5724	0.8793	0.7026	0.098*
H5C	0.4627	0.8520	0.5985	0.098*
C6	0.65389 (16)	0.4629 (4)	0.71403 (17)	0.0689 (6)
H6A	0.6486	0.2993	0.7130	0.103*
H6B	0.6810	0.5165	0.7844	0.103*
H6C	0.7048	0.5088	0.6863	0.103*
C8	0.05728 (15)	0.2340 (3)	0.43627 (13)	0.0460 (4)
H8	0.0773	0.0921	0.4684	0.055*
C9	−0.05434 (15)	0.2869 (3)	0.38041 (14)	0.0510 (5)
H9	−0.1098	0.1845	0.3761	0.061*
C10	−0.08165 (14)	0.4935 (3)	0.33139 (13)	0.0476 (5)
C11	−0.00276 (15)	0.6494 (3)	0.33688 (13)	0.0468 (5)
H11	−0.0240	0.7880	0.3018	0.056*
C12	0.10921 (14)	0.5974 (3)	0.39551 (13)	0.0424 (4)
H12	0.1638	0.7035	0.4014	0.051*

	U11	U22	U33	U12	U13	U23
C7	0.0408 (9)	0.0342 (8)	0.0392 (8)	−0.0007 (7)	0.0158 (7)	−0.0018 (7)
F1	0.0383 (7)	0.0777 (9)	0.1045 (10)	0.0076 (6)	0.0130 (7)	0.0085 (7)
O1	0.0530 (9)	0.0379 (7)	0.1041 (12)	0.0033 (6)	0.0066 (8)	0.0109 (7)
C1	0.0446 (10)	0.0361 (9)	0.0504 (10)	0.0021 (7)	0.0136 (8)	0.0031 (7)
C2	0.0405 (10)	0.0367 (9)	0.0522 (10)	0.0028 (7)	0.0134 (8)	0.0008 (7)
C3	0.0454 (11)	0.0380 (9)	0.0542 (10)	0.0017 (8)	0.0134 (8)	−0.0009 (8)
N4	0.0370 (8)	0.0433 (9)	0.0680 (10)	0.0025 (7)	0.0082 (7)	−0.0015 (7)
C5	0.0526 (12)	0.0458 (11)	0.0848 (15)	−0.0024 (9)	0.0179 (11)	−0.0022 (10)
C6	0.0416 (11)	0.0642 (13)	0.0804 (14)	0.0076 (10)	0.0080 (10)	0.0013 (11)
C8	0.0483 (10)	0.0364 (9)	0.0476 (10)	−0.0037 (7)	0.0159 (8)	0.0032 (7)
C9	0.0436 (10)	0.0489 (10)	0.0585 (11)	−0.0102 (8)	0.0206 (9)	−0.0012 (8)
C10	0.0363 (9)	0.0504 (10)	0.0501 (10)	0.0031 (8)	0.0134 (8)	−0.0041 (8)
C11	0.0483 (10)	0.0382 (9)	0.0496 (10)	0.0068 (8)	0.0175 (8)	0.0034 (7)
C12	0.0410 (9)	0.0368 (9)	0.0487 (9)	−0.0023 (7)	0.0191 (8)	0.0013 (7)

C7—C8	1.389 (2)	C5—H5B	0.9600
C7—C12	1.389 (2)	C5—H5C	0.9600
C7—C1	1.505 (2)	C6—H6A	0.9600
F1—C10	1.355 (2)	C6—H6B	0.9600
O1—C1	1.237 (2)	C6—H6C	0.9600
C1—C2	1.428 (2)	C8—C9	1.375 (2)
C2—C3	1.354 (2)	C8—H8	0.9300
C2—H2	0.9300	C9—C10	1.365 (3)
C3—N4	1.328 (2)	C9—H9	0.9300
C3—H3	0.9300	C10—C11	1.365 (3)
N4—C5	1.445 (2)	C11—C12	1.382 (2)
N4—C6	1.454 (2)	C11—H11	0.9300
C5—H5A	0.9600	C12—H12	0.9300
C8—C7—C12	118.41 (16)	N4—C6—H6A	109.5
C8—C7—C1	118.20 (15)	N4—C6—H6B	109.5
C12—C7—C1	123.39 (16)	H6A—C6—H6B	109.5
O1—C1—C2	123.30 (16)	N4—C6—H6C	109.5
O1—C1—C7	117.81 (16)	H6A—C6—H6C	109.5
C2—C1—C7	118.89 (14)	H6B—C6—H6C	109.5
C3—C2—C1	119.05 (16)	C9—C8—C7	121.44 (16)
C3—C2—H2	120.5	C9—C8—H8	119.3
C1—C2—H2	120.5	C7—C8—H8	119.3
N4—C3—C2	129.38 (17)	C10—C9—C8	118.23 (17)
N4—C3—H3	115.3	C10—C9—H9	120.9
C2—C3—H3	115.3	C8—C9—H9	120.9
C3—N4—C5	121.90 (15)	F1—C10—C9	118.63 (16)
C3—N4—C6	121.72 (16)	F1—C10—C11	118.78 (16)
C5—N4—C6	116.35 (16)	C9—C10—C11	122.59 (16)
N4—C5—H5A	109.5	C10—C11—C12	118.80 (16)
N4—C5—H5B	109.5	C10—C11—H11	120.6
H5A—C5—H5B	109.5	C12—C11—H11	120.6
N4—C5—H5C	109.5	C11—C12—C7	120.49 (16)
H5A—C5—H5C	109.5	C11—C12—H12	119.8
H5B—C5—H5C	109.5	C7—C12—H12	119.8
C8—C7—C1—O1	19.2 (3)	C1—C7—C8—C9	179.18 (16)
C12—C7—C1—O1	−160.52 (17)	C7—C8—C9—C10	1.8 (3)
C8—C7—C1—C2	−159.98 (17)	C8—C9—C10—F1	179.16 (15)
C12—C7—C1—C2	20.4 (3)	C8—C9—C10—C11	−0.8 (3)
O1—C1—C2—C3	−0.3 (3)	F1—C10—C11—C12	179.12 (15)
C7—C1—C2—C3	178.80 (16)	C9—C10—C11—C12	−0.9 (3)
C1—C2—C3—N4	−179.93 (18)	C10—C11—C12—C7	1.6 (3)
C2—C3—N4—C5	−3.2 (3)	C8—C7—C12—C11	−0.6 (3)
C2—C3—N4—C6	178.8 (2)	C1—C7—C12—C11	179.03 (15)
C12—C7—C8—C9	−1.1 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6B···O1i	0.96	2.59	3.531 (3)	168

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6B⋯O1i	0.96	2.59	3.531 (3)	168

Symmetry code: (i) .