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

Asghar, M.N.; Khan, I.U.; Arshad, M.N.; Rehman, J.

doi:10.1107/S1600536809046972

organic compounds

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ISSN: 2056-9890

Volume 65| Part 12| December 2009| Page o3063

doi:10.1107/S1600536809046972

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

Muhammad Nadeem Asghar,^a Islam Ullah Khan,^b ^* Muhammad Nadeem Arshad ^b and Jeveria Rehman ^b

^aDepartment of Chemistry, Forman Christian College (A Chartered University), Ferozpur Road Lahore 56400, Pakistan, and ^bMaterials Chemistry Laboratory, Department of Chemistry, GC University, Lahore 54000, Pakistan
^*Correspondence e-mail: iukhan.gcu@gmail.com

(Received 5 November 2009; accepted 6 November 2009; online 11 November 2009)

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, P 2₁ /c
a = 12.6079 (14) Å
b = 15.1331 (17) Å
c = 6.2182 (6) Å
β = 100.036 (5)°
V = 1168.3 (2) Å³
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[F² > 2σ(F²)] = 0.056
wR(F²) = 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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809046972/hb5213sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809046972/hb5213Isup2.hkl

checkCIF report

Comment top

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.

Related literature top

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 top

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).

Computing details top

Data collection: APEXII (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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 (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of (I) with displacement ellipsoids drawn at 50% probability level.
	Fig. 2. Unit cell packing diagram.

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

Crystal data top

C₁₃H₁₇NO	F(000) = 440
M_r = 203.28	D_x = 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 top

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

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.234	H-atom parameters constrained
S = 0.93	w = 1/[σ²(F_o²) + (0.1169P)²] where P = (F_o² + 2F_c²)/3
2779 reflections	(Δ/σ)_max < 0.001
139 parameters	Δρ_max = 0.19 e Å⁻³
0 restraints	Δρ_min = −0.15 e Å⁻³

Crystal data top

C₁₃H₁₇NO	V = 1168.3 (2) Å³
M_r = 203.28	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.6079 (14) Å	µ = 0.07 mm⁻¹
b = 15.1331 (17) Å	T = 296 K
c = 6.2182 (6) Å	0.37 × 0.33 × 0.19 mm
β = 100.036 (5)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	2779 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2007)	1051 reflections with I > 2σ(I)
T_min = 0.974, T_max = 0.986	R_int = 0.062
12449 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.056	0 restraints
wR(F²) = 0.234	H-atom parameters constrained
S = 0.93	Δρ_max = 0.19 e Å⁻³
2779 reflections	Δρ_min = −0.15 e Å⁻³
139 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
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 (Å²) top

	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, º) top

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)

Experimental details

Crystal data
Chemical formula	C₁₃H₁₇NO
M_r	203.28
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	12.6079 (14), 15.1331 (17), 6.2182 (6)
β (°)	100.036 (5)
V (Å³)	1168.3 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.37 × 0.33 × 0.19

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2007)
T_min, T_max	0.974, 0.986
No. of measured, independent and observed [I > 2σ(I)] reflections	12449, 2779, 1051
R_int	0.062
(sin θ/λ)_max (Å⁻¹)	0.658

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.056, 0.234, 0.93
No. of reflections	2779
No. of parameters	139
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.15

Computer programs: APEXII (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2009), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Acknowledgements

The authors acknowledge the Higher Education Commission of Pakistan for providing a grant under the project strengthening the Materials Chemistry Laboratory at GC University, Lahore.

References

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