(1E)-1-[4-(Dimethyl­amino)phen­yl]pent-1-en-3-one

Abstract

The title mol­ecule, C₁₃H₁₇NO, is close to planar: the dihedral angle betweent the dimethyl amino group and the benzene ring is 7.94 (19)°. No significant inter­molecular inter­actions are observed in the crystal structure.

Related literature

For background to the pharmacological effects of chalcones, see: Nielsen et al. (1998 ▶) and for their use as synthetic inter­mediates, see: Mukhtari et al. (1999 ▶). For related structures, see: Nesterov et al. (2007 ▶); Arshad et al. (2008 ▶).

Experimental

Crystal data

• C₁₃H₁₇NO

• M _r = 203.28

• Monoclinic,

• a = 12.6079 (14) Å

• b = 15.1331 (17) Å

• c = 6.2182 (6) Å

• β = 100.036 (5)°

• V = 1168.3 (2) ų

• Z = 4

• Mo Kα radiation

• μ = 0.07 mm⁻¹

• T = 296 K

• 0.37 × 0.33 × 0.19 mm

Data collection

• Bruker Kappa APEXII CCD diffractometer

• Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T _min = 0.974, T _max = 0.986

• 12449 measured reflections

• 2779 independent reflections

• 1051 reflections with I > 2σ(I)

• R _int = 0.062

Refinement

• R[F ² > 2σ(F ²)] = 0.056

• wR(F ²) = 0.234

• S = 0.93

• 2779 reflections

• 139 parameters

• H-atom parameters constrained

• Δρ_max = 0.19 e Å⁻³

• Δρ_min = −0.15 e Å⁻³

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Supplementary Material

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

supplementary crystallographic information

Comment

Chalcones are biologically active compounds (e.g. Nielsen et al., 1998) and have also been used as intermediates for the synthesis of 4-thiazolidinones (Mukhtari et al., 1999).

The title compound (I) was synthesized by the condensation reaction of 4-(dimethylamino)benzaldehyde and 2-butanol. The molecule is structurally related to the 3,5-Bis[4-(dimethylamino)benzylidene]-1-propyl-4-piperidone(II) (Nesterov et al., 2007) and (1E,4E)-1,5-Bis(4-methylphenyl)penta-1,4-dien-3-one(III) (Arshad et al., 2008). The compound is almost planer while the dimethyl amino moity is oriented at dihedral angle of 7.94 (0.19) ° to the benzene ring. No significant hydrogen bonding interaction is found in the crystal structure.

Experimental

Sodium hydroxide (0.8 g, 0.0208 mmol) was dissolved in distilled water (10 ml) and ethanol (8 ml) in a round bottom flask. The solution was cooled to room temperature. Half of the mixture of 4-(dimethylamino)benzaldehyde (1 g, 0.0083 mmol) and 2-butanol (0.60 g, 0.0083 mmol) were added to the above solution and stirred at room temperature for 15 minute then the remaining mixture was added and stirred for 2 h under the same conditions. Yellow precipitate obtained was filtered and washed with cold water. The washed precipitate was crystallized in acetone under slow evaporation to yield yellow rods of (I).

Refinement

The H-atoms for aromatic (C—H = 0.93), methyl (C—H = 0.96) and methylene (C—H = 0.97) carbon atoms were refined geometrically and treated as riding atoms: with U_iso(H) = 1.2U_eq for aromatic and methylene carbons and U_iso(H) = 1.5U_eq for methyl carbon atoms.

Figures

Fig. 1.

The molecular structure of (I) with displacement ellipsoids drawn at 50% probability level.

Fig. 2.

Unit cell packing diagram.

Crystal data

C13H17NO	F(000) = 440
Mr = 203.28	Dx = 1.156 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1287 reflections
a = 12.6079 (14) Å	θ = 2.7–21.9°
b = 15.1331 (17) Å	µ = 0.07 mm−1
c = 6.2182 (6) Å	T = 296 K
β = 100.036 (5)°	Rod, yellow
V = 1168.3 (2) Å3	0.37 × 0.33 × 0.19 mm
Z = 4

Data collection

Bruker Kappa APEXII CCD diffractometer	2779 independent reflections
Radiation source: fine-focus sealed tube	1051 reflections with I > 2σ(I)
graphite	Rint = 0.062
φ and ω scans	θmax = 27.9°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −16→16
Tmin = 0.974, Tmax = 0.986	k = −19→19
12449 measured reflections	l = −8→8

Refinement

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.234	H-atom parameters constrained
S = 0.93	w = 1/[σ2(Fo2) + (0.1169P)2] where P = (Fo2 + 2Fc2)/3
2779 reflections	(Δ/σ)max < 0.001
139 parameters	Δρmax = 0.19 e Å−3
0 restraints	Δρmin = −0.15 e Å−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
N1	−0.05777 (18)	0.36843 (15)	1.1136 (4)	0.0547 (7)
O1	0.5620 (2)	0.42215 (19)	0.7701 (4)	0.1083 (10)
C1	0.2477 (2)	0.38513 (17)	0.9326 (4)	0.0519 (7)
C2	0.1656 (2)	0.33421 (18)	0.8155 (5)	0.0563 (8)
H2	0.1790	0.3029	0.6944	0.068*
C3	0.0653 (2)	0.32866 (18)	0.8728 (4)	0.0529 (8)
H3	0.0121	0.2947	0.7888	0.063*
C4	0.0421 (2)	0.37361 (17)	1.0567 (4)	0.0472 (7)
C5	0.1260 (2)	0.42154 (18)	1.1781 (4)	0.0539 (8)
H5	0.1145	0.4506	1.3037	0.065*
C6	0.2252 (2)	0.42703 (19)	1.1174 (5)	0.0577 (8)
H6	0.2790	0.4599	1.2029	0.069*
C7	0.3527 (2)	0.39618 (19)	0.8680 (5)	0.0601 (8)
H7	0.4020	0.4306	0.9604	0.072*
C8	0.3862 (2)	0.3640 (2)	0.6976 (5)	0.0628 (8)
H8	0.3395	0.3287	0.6017	0.075*
C9	0.4952 (3)	0.3811 (2)	0.6492 (5)	0.0633 (9)
C10	0.5181 (3)	0.3440 (3)	0.4438 (5)	0.0832 (11)
H10A	0.4650	0.3670	0.3252	0.100*
H10B	0.5081	0.2805	0.4476	0.100*
C11	0.6267 (3)	0.3614 (3)	0.3914 (6)	0.0963 (12)
H11A	0.6404	0.4238	0.3967	0.144*
H11B	0.6299	0.3396	0.2477	0.144*
H11C	0.6801	0.3319	0.4960	0.144*
C12	−0.1486 (2)	0.3348 (2)	0.9610 (5)	0.0707 (9)
H12A	−0.1530	0.3648	0.8236	0.106*
H12B	−0.2137	0.3447	1.0178	0.106*
H12C	−0.1395	0.2726	0.9402	0.106*
C13	−0.0816 (3)	0.4196 (2)	1.2966 (5)	0.0650 (9)
H13A	−0.0345	0.4018	1.4277	0.097*
H13B	−0.1550	0.4097	1.3127	0.097*
H13C	−0.0711	0.4813	1.2706	0.097*

Atomic displacement parameters (Ų)

	U11	U22	U33	U12	U13	U23
N1	0.0483 (15)	0.0563 (15)	0.0600 (14)	−0.0042 (11)	0.0104 (11)	−0.0056 (12)
O1	0.0766 (18)	0.148 (3)	0.1051 (19)	−0.0394 (16)	0.0280 (15)	−0.0576 (18)
C1	0.0488 (17)	0.0481 (17)	0.0581 (17)	−0.0005 (13)	0.0077 (14)	0.0043 (14)
C2	0.063 (2)	0.0501 (18)	0.0582 (17)	0.0022 (15)	0.0170 (15)	−0.0019 (14)
C3	0.0561 (19)	0.0445 (17)	0.0564 (17)	−0.0048 (13)	0.0049 (14)	−0.0052 (13)
C4	0.0492 (17)	0.0371 (15)	0.0555 (16)	−0.0001 (13)	0.0094 (14)	0.0048 (13)
C5	0.057 (2)	0.0529 (18)	0.0518 (16)	−0.0017 (14)	0.0089 (14)	−0.0070 (13)
C6	0.0516 (19)	0.0588 (19)	0.0598 (18)	−0.0061 (14)	0.0015 (14)	−0.0066 (15)
C7	0.058 (2)	0.058 (2)	0.0621 (18)	0.0016 (15)	0.0047 (15)	−0.0015 (15)
C8	0.058 (2)	0.064 (2)	0.0653 (19)	−0.0031 (16)	0.0067 (16)	−0.0058 (16)
C9	0.054 (2)	0.068 (2)	0.0689 (19)	−0.0046 (16)	0.0129 (16)	−0.0040 (16)
C10	0.064 (2)	0.111 (3)	0.077 (2)	−0.007 (2)	0.0190 (17)	−0.019 (2)
C11	0.072 (2)	0.125 (3)	0.099 (3)	0.000 (2)	0.034 (2)	−0.017 (2)
C12	0.056 (2)	0.075 (2)	0.082 (2)	−0.0110 (17)	0.0134 (17)	−0.0093 (18)
C13	0.067 (2)	0.066 (2)	0.0651 (19)	0.0049 (16)	0.0215 (15)	0.0024 (16)

Geometric parameters (Å, °)

N1—C4	1.368 (3)	C7—H7	0.9300
N1—C12	1.447 (3)	C8—C9	1.480 (4)
N1—C13	1.451 (4)	C8—H8	0.9300
O1—C9	1.200 (3)	C9—C10	1.469 (4)
C1—C6	1.385 (4)	C10—C11	1.485 (4)
C1—C2	1.390 (4)	C10—H10A	0.9700
C1—C7	1.458 (4)	C10—H10B	0.9700
C2—C3	1.375 (4)	C11—H11A	0.9600
C2—H2	0.9300	C11—H11B	0.9600
C3—C4	1.404 (3)	C11—H11C	0.9600
C3—H3	0.9300	C12—H12A	0.9600
C4—C5	1.391 (4)	C12—H12B	0.9600
C5—C6	1.370 (4)	C12—H12C	0.9600
C5—H5	0.9300	C13—H13A	0.9600
C6—H6	0.9300	C13—H13B	0.9600
C7—C8	1.302 (4)	C13—H13C	0.9600
C4—N1—C12	120.6 (2)	O1—C9—C10	121.3 (3)
C4—N1—C13	119.9 (2)	O1—C9—C8	122.6 (3)
C12—N1—C13	117.0 (2)	C10—C9—C8	116.1 (3)
C6—C1—C2	116.5 (3)	C9—C10—C11	116.9 (3)
C6—C1—C7	120.2 (3)	C9—C10—H10A	108.1
C2—C1—C7	123.2 (3)	C11—C10—H10A	108.1
C3—C2—C1	122.2 (3)	C9—C10—H10B	108.1
C3—C2—H2	118.9	C11—C10—H10B	108.1
C1—C2—H2	118.9	H10A—C10—H10B	107.3
C2—C3—C4	120.8 (3)	C10—C11—H11A	109.5
C2—C3—H3	119.6	C10—C11—H11B	109.5
C4—C3—H3	119.6	H11A—C11—H11B	109.5
N1—C4—C5	122.4 (2)	C10—C11—H11C	109.5
N1—C4—C3	120.9 (3)	H11A—C11—H11C	109.5
C5—C4—C3	116.6 (3)	H11B—C11—H11C	109.5
C6—C5—C4	121.7 (3)	N1—C12—H12A	109.5
C6—C5—H5	119.1	N1—C12—H12B	109.5
C4—C5—H5	119.1	H12A—C12—H12B	109.5
C5—C6—C1	122.0 (3)	N1—C12—H12C	109.5
C5—C6—H6	119.0	H12A—C12—H12C	109.5
C1—C6—H6	119.0	H12B—C12—H12C	109.5
C8—C7—C1	128.4 (3)	N1—C13—H13A	109.5
C8—C7—H7	115.8	N1—C13—H13B	109.5
C1—C7—H7	115.8	H13A—C13—H13B	109.5
C7—C8—C9	123.0 (3)	N1—C13—H13C	109.5
C7—C8—H8	118.5	H13A—C13—H13C	109.5
C9—C8—H8	118.5	H13B—C13—H13C	109.5
C6—C1—C2—C3	3.0 (4)	C4—C5—C6—C1	−0.2 (4)
C7—C1—C2—C3	−176.3 (3)	C2—C1—C6—C5	−2.4 (4)
C1—C2—C3—C4	−1.1 (4)	C7—C1—C6—C5	177.0 (3)
C12—N1—C4—C5	166.5 (3)	C6—C1—C7—C8	−177.9 (3)
C13—N1—C4—C5	4.9 (4)	C2—C1—C7—C8	1.4 (5)
C12—N1—C4—C3	−14.8 (4)	C1—C7—C8—C9	179.4 (3)
C13—N1—C4—C3	−176.4 (2)	C7—C8—C9—O1	3.8 (5)
C2—C3—C4—N1	179.8 (3)	C7—C8—C9—C10	−176.6 (3)
C2—C3—C4—C5	−1.4 (4)	O1—C9—C10—C11	−1.2 (5)
N1—C4—C5—C6	−179.1 (2)	C8—C9—C10—C11	179.3 (3)
C3—C4—C5—C6	2.1 (4)