3-[4-(Dimethyl­amino)phenyl]-1-(3-pyridyl)prop-2-en-1-one

Jayarama, A.; Ng, S.W.

doi:10.1107/S1600536809013956

organic compounds

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ISSN: 2056-9890

Volume 65| Part 5| May 2009| Page o1066

doi:10.1107/S1600536809013956

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3-[4-(Dimethylamino)phenyl]-1-(3-pyridyl)prop-2-en-1-one

A. Jayarama ^a and Seik Weng Ng ^b ^*

^aDepartment of Physics, Mangalore Institute of Technology and Engineering, Badagamijar, Moodabidri 574 225, India, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 13 April 2009; accepted 14 April 2009; online 18 April 2009)

The pyridyl and aryl rings in the title compound, C₁₆H₁₆N₂O, which are located at the ends of the propenone unit, are inclined at an angle of 17.1 (1)° with respect to each other.

Related literature

For 3-(4-chlorophenyl)-1-(3-pyridyl)prop-2-en-1-one, which crystallizes in a non-centrosymmetric space group, see: Uchida et al. (1998 ). For the general synthesis by the Claisen–Schmidt condensation, see: Vogel (1999 ). For literature on related compounds exhibiting second-harmonic generation activity, see: Gu et al. (2008 ); Ravindra et al. (2008a ,b ).

Experimental

Crystal data

C₁₆H₁₆N₂O
M_r = 252.31
Monoclinic, C 2/c
a = 14.6672 (6) Å
b = 11.0644 (4) Å
c = 16.7272 (6) Å
β = 107.205 (3)°
V = 2593.1 (2) Å³
Z = 8
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 100 K
0.20 × 0.20 × 0.03 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: none
11747 measured reflections
2976 independent reflections
1817 reflections with I > 2˘I)
R_int = 0.063

Refinement

R[F² > 2σ(F²)] = 0.055
wR(F²) = 0.147
S = 1.02
2976 reflections
174 parameters
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.28 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: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809013956/bt2931sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809013956/bt2931Isup2.hkl

checkCIF report

Comment top

Some chalcone derivatives exhibit high second-harmonic generation conversion efficiency (Gu et al., 2008; Ravindra et al., 2008a,b). The title compound was synthesized for the purpose of examining this property; unfortunately, the compound crystallizes in a centrosymmetric space group.

Related literature top

For 3-(4-chlorophenyl)-1-(pyrid-3-yl)prop-2-en-1-one, which crystallizes in a non-centrosymmetric space group, see: Uchida et al. (1998). For the general synthesis by the Claisen–Schmidt condensation, see: Vogel (1999). For literature on related compounds exhibiting second-harmonic generation activity, see: Gu et al. (2008); Ravindra et al. (2008a,b).

Experimental top

The compound was synthesized by the Claisen–Schmidt condensation (Vogel, 1999). To a mixture of ethanol (20 ml) and 10% sodium hydroxide solution (5 ml) was added an ethanol (15 ml) solution of 3-acetyl pyridine (0.001 mol) and 4-dimethylaminobenzaldehyde (0.001 mol). The temperature of the mixture was maintained at below 298 K for 2 h. The solid product that formed was washed with water. The compound was recrystallized from methanol.

Computing details top

Data collection: APEX2 (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: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2009).

Figures top

Fig. 1. Anisotropic displacement ellipsoid plot (Barbour, 2001) of C₁₆H₁₆N₂O at the 70% probability level. H atoms are drawn as spheres of arbitrary radius.

3-[4-(Dimethylamino)phenyl]-1-(3-pyridyl)prop-2-en-1-one top

Crystal data top

C₁₆H₁₆N₂O	F(000) = 1072
M_r = 252.31	D_x = 1.293 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 1330 reflections
a = 14.6672 (6) Å	θ = 2.5–24.9°
b = 11.0644 (4) Å	µ = 0.08 mm⁻¹
c = 16.7272 (6) Å	T = 100 K
β = 107.205 (3)°	Plate, orange
V = 2593.1 (2) Å³	0.20 × 0.20 × 0.03 mm
Z = 8

Data collection top

Bruker SMART APEX diffractometer	1817 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.063
Graphite monochromator	θ_max = 27.5°, θ_min = 2.4°
ω scans	h = −19→18
11747 measured reflections	k = −14→14
2976 independent reflections	l = −21→21

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.147	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0648P)² + 0.8849P] where P = (F_o² + 2F_c²)/3
2976 reflections	(Δ/σ)_max = 0.001
174 parameters	Δρ_max = 0.22 e Å⁻³
0 restraints	Δρ_min = −0.28 e Å⁻³

Crystal data top

C₁₆H₁₆N₂O	V = 2593.1 (2) Å³
M_r = 252.31	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 14.6672 (6) Å	µ = 0.08 mm⁻¹
b = 11.0644 (4) Å	T = 100 K
c = 16.7272 (6) Å	0.20 × 0.20 × 0.03 mm
β = 107.205 (3)°

Data collection top

Bruker SMART APEX diffractometer	1817 reflections with I > 2σ(I)
11747 measured reflections	R_int = 0.063
2976 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.055	0 restraints
wR(F²) = 0.147	H-atom parameters constrained
S = 1.02	Δρ_max = 0.22 e Å⁻³
2976 reflections	Δρ_min = −0.28 e Å⁻³
174 parameters

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

	x	y	z	U_iso*/U_eq
O1	0.70214 (10)	0.23165 (12)	0.74962 (8)	0.0328 (4)
N1	0.60015 (14)	0.57819 (16)	0.86721 (11)	0.0408 (5)
N2	0.89331 (12)	0.58854 (14)	0.38128 (10)	0.0270 (4)
C1	0.55057 (16)	0.5062 (2)	0.90340 (14)	0.0394 (6)
H1	0.5185	0.5423	0.9390	0.047*
C2	0.54329 (15)	0.3828 (2)	0.89203 (13)	0.0314 (5)
H2	0.5073	0.3354	0.9192	0.038*
C3	0.58905 (14)	0.33046 (18)	0.84076 (12)	0.0273 (5)
H3	0.5855	0.2455	0.8322	0.033*
C4	0.64088 (13)	0.40126 (16)	0.80103 (11)	0.0242 (4)
C5	0.64452 (15)	0.52517 (17)	0.81678 (12)	0.0292 (5)
H5	0.6802	0.5746	0.7905	0.035*
C6	0.69040 (13)	0.34254 (16)	0.74515 (12)	0.0240 (4)
C7	0.72162 (14)	0.41654 (17)	0.68607 (12)	0.0268 (5)
H7	0.7108	0.5013	0.6846	0.032*
C8	0.76531 (13)	0.36800 (17)	0.63362 (11)	0.0250 (4)
H8	0.7750	0.2831	0.6380	0.030*
C9	0.79945 (13)	0.42798 (16)	0.57141 (11)	0.0226 (4)
C10	0.83957 (14)	0.35986 (17)	0.51975 (12)	0.0259 (5)
H10	0.8451	0.2748	0.5277	0.031*
C11	0.87122 (14)	0.41098 (16)	0.45818 (12)	0.0254 (4)
H11	0.8973	0.3610	0.4243	0.030*
C12	0.86545 (13)	0.53701 (16)	0.44457 (11)	0.0225 (4)
C13	0.82739 (14)	0.60643 (17)	0.49786 (12)	0.0258 (5)
H13	0.8240	0.6918	0.4916	0.031*
C14	0.79515 (14)	0.55355 (17)	0.55848 (12)	0.0258 (4)
H14	0.7692	0.6032	0.5927	0.031*
C15	0.93708 (15)	0.51553 (18)	0.33043 (13)	0.0316 (5)
H15A	0.8972	0.4445	0.3097	0.047*
H15B	1.0006	0.4894	0.3644	0.047*
H15C	0.9429	0.5635	0.2829	0.047*
C16	0.91164 (16)	0.71857 (17)	0.38199 (13)	0.0332 (5)
H16A	0.8521	0.7627	0.3761	0.050*
H16B	0.9364	0.7392	0.3353	0.050*
H16C	0.9587	0.7409	0.4350	0.050*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0461 (9)	0.0199 (7)	0.0374 (8)	−0.0033 (6)	0.0201 (7)	−0.0016 (6)
N1	0.0568 (13)	0.0308 (10)	0.0438 (11)	0.0060 (9)	0.0286 (10)	0.0004 (8)
N2	0.0349 (10)	0.0210 (8)	0.0292 (9)	0.0003 (7)	0.0159 (8)	0.0011 (7)
C1	0.0485 (15)	0.0406 (13)	0.0372 (13)	0.0114 (11)	0.0252 (12)	0.0032 (10)
C2	0.0320 (12)	0.0370 (12)	0.0291 (11)	−0.0004 (9)	0.0152 (9)	0.0073 (9)
C3	0.0316 (11)	0.0232 (10)	0.0268 (11)	−0.0005 (9)	0.0083 (9)	0.0011 (8)
C4	0.0254 (10)	0.0241 (10)	0.0228 (10)	0.0011 (8)	0.0069 (8)	0.0009 (8)
C5	0.0373 (12)	0.0242 (10)	0.0307 (11)	0.0013 (9)	0.0170 (10)	0.0012 (8)
C6	0.0268 (11)	0.0210 (10)	0.0245 (10)	−0.0036 (8)	0.0079 (9)	−0.0016 (8)
C7	0.0311 (11)	0.0207 (10)	0.0295 (11)	0.0012 (8)	0.0105 (9)	0.0016 (8)
C8	0.0302 (11)	0.0196 (9)	0.0262 (10)	−0.0024 (8)	0.0099 (9)	−0.0016 (8)
C9	0.0231 (10)	0.0207 (9)	0.0248 (10)	−0.0010 (8)	0.0084 (8)	−0.0013 (8)
C10	0.0318 (11)	0.0179 (9)	0.0289 (11)	−0.0004 (8)	0.0106 (9)	−0.0005 (8)
C11	0.0292 (11)	0.0211 (10)	0.0281 (10)	0.0001 (8)	0.0119 (9)	−0.0046 (8)
C12	0.0216 (10)	0.0226 (10)	0.0231 (10)	−0.0014 (8)	0.0065 (8)	−0.0003 (8)
C13	0.0315 (11)	0.0163 (9)	0.0311 (11)	0.0000 (8)	0.0115 (9)	−0.0004 (8)
C14	0.0285 (11)	0.0216 (9)	0.0302 (11)	0.0024 (8)	0.0130 (9)	−0.0023 (8)
C15	0.0349 (12)	0.0307 (11)	0.0335 (11)	−0.0019 (9)	0.0164 (10)	0.0003 (9)
C16	0.0405 (13)	0.0233 (10)	0.0394 (12)	−0.0023 (9)	0.0174 (10)	0.0045 (9)

Geometric parameters (Å, º) top

O1—C6	1.238 (2)	C8—C9	1.443 (2)
N1—C1	1.338 (3)	C8—H8	0.9500
N1—C5	1.343 (2)	C9—C10	1.401 (2)
N2—C12	1.367 (2)	C9—C14	1.405 (3)
N2—C15	1.453 (2)	C10—C11	1.371 (3)
N2—C16	1.463 (2)	C10—H10	0.9500
C1—C2	1.378 (3)	C11—C12	1.411 (2)
C1—H1	0.9500	C11—H11	0.9500
C2—C3	1.365 (3)	C12—C13	1.411 (3)
C2—H2	0.9500	C13—C14	1.370 (3)
C3—C4	1.390 (3)	C13—H13	0.9500
C3—H3	0.9500	C14—H14	0.9500
C4—C5	1.394 (3)	C15—H15A	0.9800
C4—C6	1.492 (2)	C15—H15B	0.9800
C5—H5	0.9500	C15—H15C	0.9800
C6—C7	1.458 (3)	C16—H16A	0.9800
C7—C8	1.342 (2)	C16—H16B	0.9800
C7—H7	0.9500	C16—H16C	0.9800

C1—N1—C5	116.96 (18)	C10—C9—C8	119.74 (17)
C12—N2—C15	120.43 (15)	C14—C9—C8	123.82 (17)
C12—N2—C16	120.01 (16)	C11—C10—C9	122.61 (17)
C15—N2—C16	116.07 (16)	C11—C10—H10	118.7
N1—C1—C2	123.9 (2)	C9—C10—H10	118.7
N1—C1—H1	118.1	C10—C11—C12	120.76 (18)
C2—C1—H1	118.1	C10—C11—H11	119.6
C3—C2—C1	118.4 (2)	C12—C11—H11	119.6
C3—C2—H2	120.8	N2—C12—C13	121.80 (16)
C1—C2—H2	120.8	N2—C12—C11	121.30 (17)
C2—C3—C4	120.10 (18)	C13—C12—C11	116.87 (17)
C2—C3—H3	120.0	C14—C13—C12	121.51 (17)
C4—C3—H3	120.0	C14—C13—H13	119.2
C3—C4—C5	117.36 (18)	C12—C13—H13	119.2
C3—C4—C6	119.39 (17)	C13—C14—C9	121.77 (18)
C5—C4—C6	123.24 (17)	C13—C14—H14	119.1
N1—C5—C4	123.34 (19)	C9—C14—H14	119.1
N1—C5—H5	118.3	N2—C15—H15A	109.5
C4—C5—H5	118.3	N2—C15—H15B	109.5
O1—C6—C7	122.12 (17)	H15A—C15—H15B	109.5
O1—C6—C4	118.59 (17)	N2—C15—H15C	109.5
C7—C6—C4	119.28 (16)	H15A—C15—H15C	109.5
C8—C7—C6	121.66 (17)	H15B—C15—H15C	109.5
C8—C7—H7	119.2	N2—C16—H16A	109.5
C6—C7—H7	119.2	N2—C16—H16B	109.5
C7—C8—C9	128.46 (18)	H16A—C16—H16B	109.5
C7—C8—H8	115.8	N2—C16—H16C	109.5
C9—C8—H8	115.8	H16A—C16—H16C	109.5
C10—C9—C14	116.44 (17)	H16B—C16—H16C	109.5

C5—N1—C1—C2	0.3 (3)	C7—C8—C9—C14	2.9 (3)
N1—C1—C2—C3	−0.1 (3)	C14—C9—C10—C11	−1.5 (3)
C1—C2—C3—C4	−0.4 (3)	C8—C9—C10—C11	178.42 (18)
C2—C3—C4—C5	0.8 (3)	C9—C10—C11—C12	0.6 (3)
C2—C3—C4—C6	−179.95 (18)	C15—N2—C12—C13	176.60 (17)
C1—N1—C5—C4	0.1 (3)	C16—N2—C12—C13	18.5 (3)
C3—C4—C5—N1	−0.6 (3)	C15—N2—C12—C11	−5.1 (3)
C6—C4—C5—N1	−179.85 (19)	C16—N2—C12—C11	−163.19 (18)
C3—C4—C6—O1	−15.8 (3)	C10—C11—C12—N2	−177.40 (18)
C5—C4—C6—O1	163.44 (19)	C10—C11—C12—C13	1.0 (3)
C3—C4—C6—C7	162.98 (18)	N2—C12—C13—C14	176.66 (18)
C5—C4—C6—C7	−17.8 (3)	C11—C12—C13—C14	−1.7 (3)
O1—C6—C7—C8	−0.4 (3)	C12—C13—C14—C9	0.8 (3)
C4—C6—C7—C8	−179.08 (18)	C10—C9—C14—C13	0.8 (3)
C6—C7—C8—C9	179.34 (18)	C8—C9—C14—C13	−179.16 (18)
C7—C8—C9—C10	−177.03 (19)

Experimental details

Crystal data
Chemical formula	C₁₆H₁₆N₂O
M_r	252.31
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	100
a, b, c (Å)	14.6672 (6), 11.0644 (4), 16.7272 (6)
β (°)	107.205 (3)
V (Å³)	2593.1 (2)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.20 × 0.20 × 0.03

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	11747, 2976, 1817
R_int	0.063
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.055, 0.147, 1.02
No. of reflections	2976
No. of parameters	174
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.28

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2009).

Acknowledgements

The authors thank the Mangalore Institute of Technology and Engineering and the University of Malaya for supporting this study.

References

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