3-(3,4-Dimethoxy­phenyl)-1-(3-pyridyl)prop-2-en-1-one monohydrate

Jayarama, A.; Ng, S.W.

doi:10.1107/S1600536809013944

organic compounds

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ISSN: 2056-9890

Volume 65| Part 5| May 2009| Page o1065

doi:10.1107/S1600536809013944

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3-(3,4-Dimethoxyphenyl)-1-(3-pyridyl)prop-2-en-1-one monohydrate

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, C₁₆H₁₅NO₃·H₂O, which are located at the ends of the propenone unit, are nearly coplanar with this unit [dihedral angles = 3.74 (14) and 5.06 (13)°, respectively]; the rings are inclined at an angle of 6.2 (1)° with respect to each other. The solvent water molecule forms hydrogen bonds with the pyridyl N atom and also with a symmetry-related water molecule.

Related literature

For 3-(4-chlorophenyl)-1-(3-pyridyl)prop-2-en-1-one, which belongs to 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

C₁₆H₁₅NO₃·H₂O
M_r = 287.31
Monoclinic, P 2₁ /n
a = 17.9809 (4) Å
b = 4.5004 (1) Å
c = 18.2230 (4) Å
β = 101.775 (2)°
V = 1443.60 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 100 K
0.20 × 0.15 × 0.10 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: none
12630 measured reflections
3315 independent reflections
2362 reflections with I > 2σI)
R_int = 0.041

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.126
S = 1.02
3315 reflections
200 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.52 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H11⋯N1	0.83 (1)	2.05 (1)	2.857 (2)	163 (2)
O1W—H12⋯O1Wⁱ	0.85 (1)	1.94 (3)	2.763 (2)	162 (7)
Symmetry code: (i) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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/S1600536809013944/bt2930sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809013944/bt2930Isup2.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-(3-pyridyl)prop-2-en-1-one, which belongs to 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 3,4-dimethoxybenzaldehyde (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 the title compound at the 70% probability level. H atoms are drawn as spheres of arbitrary radius.

3-(3,4-Dimethoxyphenyl)-1-(3-pyridyl)prop-2-en-1-one monohydrate top

Crystal data top

C₁₆H₁₅NO₃·H₂O	F(000) = 608
M_r = 287.31	D_x = 1.322 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2693 reflections
a = 17.9809 (4) Å	θ = 2.3–28.2°
b = 4.5004 (1) Å	µ = 0.10 mm⁻¹
c = 18.2230 (4) Å	T = 100 K
β = 101.775 (2)°	Prism, yellow
V = 1443.60 (6) Å³	0.20 × 0.15 × 0.10 mm
Z = 4

Data collection top

Bruker SMART APEX diffractometer	2362 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.041
Graphite monochromator	θ_max = 27.5°, θ_min = 1.5°
ω scans	h = −23→23
12630 measured reflections	k = −5→5
3315 independent reflections	l = −23→23

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) = 0.126	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.0628P)² + 0.3539P] where P = (F_o² + 2F_c²)/3
3315 reflections	(Δ/σ)_max = 0.001
200 parameters	Δρ_max = 0.52 e Å⁻³
2 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₁₆H₁₅NO₃·H₂O	V = 1443.60 (6) Å³
M_r = 287.31	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 17.9809 (4) Å	µ = 0.10 mm⁻¹
b = 4.5004 (1) Å	T = 100 K
c = 18.2230 (4) Å	0.20 × 0.15 × 0.10 mm
β = 101.775 (2)°

Data collection top

Bruker SMART APEX diffractometer	2362 reflections with I > 2σ(I)
12630 measured reflections	R_int = 0.041
3315 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	2 restraints
wR(F²) = 0.126	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.52 e Å⁻³
3315 reflections	Δρ_min = −0.20 e Å⁻³
200 parameters

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

	x	y	z	U_iso*/U_eq
O1	0.41877 (6)	0.8369 (3)	0.27622 (7)	0.0397 (3)
O2	0.80564 (6)	0.3782 (3)	0.50243 (6)	0.0340 (3)
O3	0.76194 (6)	0.0474 (3)	0.59966 (6)	0.0332 (3)
O1W	0.74070 (7)	1.5349 (3)	0.20508 (8)	0.0402 (3)
H11	0.6951 (6)	1.524 (5)	0.1836 (11)	0.059 (7)*
H12	0.748 (4)	1.409 (13)	0.241 (3)	0.27 (3)*
N1	0.58178 (7)	1.4202 (3)	0.15840 (8)	0.0308 (3)
C1	0.52118 (9)	1.5143 (4)	0.10854 (9)	0.0316 (4)
H1	0.5290	1.6520	0.0713	0.038*
C2	0.44804 (9)	1.4221 (4)	0.10827 (10)	0.0351 (4)
H2	0.4066	1.4938	0.0716	0.042*
C3	0.43629 (8)	1.2243 (4)	0.16218 (9)	0.0313 (4)
H3	0.3864	1.1582	0.1633	0.038*
C4	0.49781 (8)	1.1211 (3)	0.21511 (8)	0.0251 (3)
C5	0.56925 (8)	1.2269 (4)	0.21027 (9)	0.0279 (4)
H5	0.6118	1.1577	0.2460	0.034*
C6	0.48429 (8)	0.9066 (4)	0.27391 (9)	0.0271 (4)
C7	0.54975 (8)	0.7857 (4)	0.32741 (9)	0.0274 (4)
H7	0.5996	0.8515	0.3257	0.033*
C8	0.53984 (8)	0.5844 (4)	0.37843 (9)	0.0265 (3)
H8	0.4889	0.5264	0.3777	0.032*
C9	0.59780 (8)	0.4441 (3)	0.43488 (8)	0.0244 (3)
C10	0.67609 (8)	0.4868 (4)	0.43855 (9)	0.0260 (3)
H10	0.6927	0.6099	0.4027	0.031*
C11	0.72834 (8)	0.3517 (4)	0.49363 (9)	0.0262 (3)
C12	0.70494 (8)	0.1676 (3)	0.54753 (9)	0.0267 (4)
C13	0.62805 (9)	0.1256 (4)	0.54443 (9)	0.0279 (4)
H13	0.6114	0.0045	0.5806	0.034*
C14	0.57558 (8)	0.2614 (4)	0.48808 (9)	0.0267 (3)
H14	0.5230	0.2288	0.4858	0.032*
C15	0.83247 (9)	0.5723 (4)	0.45185 (10)	0.0317 (4)
H15A	0.8881	0.5795	0.4644	0.048*
H15B	0.8120	0.7721	0.4558	0.048*
H15C	0.8158	0.4988	0.4005	0.048*
C16	0.74125 (10)	−0.1299 (4)	0.65737 (10)	0.0365 (4)
H16A	0.7872	−0.1916	0.6929	0.055*
H16B	0.7136	−0.3063	0.6350	0.055*
H16C	0.7088	−0.0136	0.6838	0.055*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0184 (6)	0.0609 (9)	0.0394 (7)	−0.0013 (5)	0.0049 (5)	0.0074 (6)
O2	0.0173 (5)	0.0427 (7)	0.0417 (7)	0.0009 (5)	0.0052 (5)	0.0096 (6)
O3	0.0228 (5)	0.0391 (7)	0.0363 (7)	0.0030 (5)	0.0029 (5)	0.0096 (5)
O1W	0.0225 (6)	0.0420 (7)	0.0526 (8)	−0.0010 (5)	−0.0007 (6)	0.0041 (7)
N1	0.0228 (6)	0.0373 (8)	0.0318 (7)	−0.0007 (6)	0.0042 (5)	−0.0019 (6)
C1	0.0300 (8)	0.0321 (9)	0.0312 (9)	−0.0011 (7)	0.0031 (7)	0.0003 (7)
C2	0.0250 (8)	0.0379 (10)	0.0383 (10)	0.0003 (7)	−0.0034 (7)	0.0035 (8)
C3	0.0200 (7)	0.0346 (9)	0.0368 (9)	−0.0010 (7)	0.0005 (7)	−0.0015 (8)
C4	0.0205 (7)	0.0283 (8)	0.0256 (8)	0.0018 (6)	0.0030 (6)	−0.0062 (6)
C5	0.0202 (7)	0.0346 (9)	0.0280 (8)	0.0030 (6)	0.0027 (6)	−0.0035 (7)
C6	0.0215 (7)	0.0328 (9)	0.0267 (8)	0.0023 (6)	0.0038 (6)	−0.0050 (7)
C7	0.0198 (7)	0.0317 (9)	0.0295 (8)	0.0003 (6)	0.0027 (6)	−0.0043 (7)
C8	0.0195 (7)	0.0307 (8)	0.0289 (8)	0.0004 (6)	0.0036 (6)	−0.0069 (7)
C9	0.0215 (7)	0.0244 (8)	0.0268 (8)	−0.0004 (6)	0.0036 (6)	−0.0063 (6)
C10	0.0218 (7)	0.0276 (8)	0.0290 (8)	−0.0001 (6)	0.0063 (6)	−0.0018 (7)
C11	0.0181 (7)	0.0289 (8)	0.0320 (8)	−0.0002 (6)	0.0060 (6)	−0.0028 (7)
C12	0.0230 (7)	0.0264 (8)	0.0298 (8)	0.0026 (6)	0.0030 (6)	−0.0027 (7)
C13	0.0264 (8)	0.0271 (8)	0.0308 (8)	−0.0021 (6)	0.0069 (6)	−0.0013 (7)
C14	0.0194 (7)	0.0279 (8)	0.0328 (8)	−0.0021 (6)	0.0056 (6)	−0.0038 (7)
C15	0.0213 (7)	0.0362 (9)	0.0386 (9)	−0.0026 (7)	0.0085 (7)	0.0014 (8)
C16	0.0334 (9)	0.0400 (10)	0.0357 (9)	0.0040 (8)	0.0059 (7)	0.0078 (8)

Geometric parameters (Å, º) top

O1—C6	1.2282 (18)	C7—C8	1.336 (2)
O2—C11	1.3714 (17)	C7—H7	0.9500
O2—C15	1.4237 (19)	C8—C9	1.451 (2)
O3—C12	1.3596 (18)	C8—H8	0.9500
O3—C16	1.429 (2)	C9—C14	1.390 (2)
O1W—H11	0.84 (1)	C9—C10	1.409 (2)
O1W—H12	0.85 (1)	C10—C11	1.369 (2)
N1—C1	1.337 (2)	C10—H10	0.9500
N1—C5	1.337 (2)	C11—C12	1.413 (2)
C1—C2	1.378 (2)	C12—C13	1.385 (2)
C1—H1	0.9500	C13—C14	1.387 (2)
C2—C3	1.374 (2)	C13—H13	0.9500
C2—H2	0.9500	C14—H14	0.9500
C3—C4	1.391 (2)	C15—H15A	0.9800
C3—H3	0.9500	C15—H15B	0.9800
C4—C5	1.390 (2)	C15—H15C	0.9800
C4—C6	1.499 (2)	C16—H16A	0.9800
C5—H5	0.9500	C16—H16B	0.9800
C6—C7	1.471 (2)	C16—H16C	0.9800

C11—O2—C15	116.54 (12)	C14—C9—C8	118.98 (13)
C12—O3—C16	117.66 (12)	C10—C9—C8	122.71 (14)
H11—O1W—H12	108 (5)	C11—C10—C9	120.24 (15)
C1—N1—C5	117.06 (13)	C11—C10—H10	119.9
N1—C1—C2	123.50 (16)	C9—C10—H10	119.9
N1—C1—H1	118.3	C10—C11—O2	125.07 (14)
C2—C1—H1	118.3	C10—C11—C12	120.85 (14)
C3—C2—C1	118.58 (15)	O2—C11—C12	114.08 (13)
C3—C2—H2	120.7	O3—C12—C13	125.32 (14)
C1—C2—H2	120.7	O3—C12—C11	115.47 (13)
C2—C3—C4	119.73 (15)	C13—C12—C11	119.21 (14)
C2—C3—H3	120.1	C12—C13—C14	119.52 (15)
C4—C3—H3	120.1	C12—C13—H13	120.2
C5—C4—C3	117.15 (15)	C14—C13—H13	120.2
C5—C4—C6	123.58 (14)	C13—C14—C9	121.87 (14)
C3—C4—C6	119.27 (14)	C13—C14—H14	119.1
N1—C5—C4	123.99 (14)	C9—C14—H14	119.1
N1—C5—H5	118.0	O2—C15—H15A	109.5
C4—C5—H5	118.0	O2—C15—H15B	109.5
O1—C6—C7	121.76 (15)	H15A—C15—H15B	109.5
O1—C6—C4	119.06 (14)	O2—C15—H15C	109.5
C7—C6—C4	119.17 (13)	H15A—C15—H15C	109.5
C8—C7—C6	120.64 (14)	H15B—C15—H15C	109.5
C8—C7—H7	119.7	O3—C16—H16A	109.5
C6—C7—H7	119.7	O3—C16—H16B	109.5
C7—C8—C9	127.59 (14)	H16A—C16—H16B	109.5
C7—C8—H8	116.2	O3—C16—H16C	109.5
C9—C8—H8	116.2	H16A—C16—H16C	109.5
C14—C9—C10	118.31 (14)	H16B—C16—H16C	109.5

C5—N1—C1—C2	−0.1 (2)	C14—C9—C10—C11	−0.3 (2)
N1—C1—C2—C3	0.4 (3)	C8—C9—C10—C11	179.17 (14)
C1—C2—C3—C4	−0.3 (3)	C9—C10—C11—O2	−179.94 (14)
C2—C3—C4—C5	0.1 (2)	C9—C10—C11—C12	0.1 (2)
C2—C3—C4—C6	179.67 (15)	C15—O2—C11—C10	2.9 (2)
C1—N1—C5—C4	−0.2 (2)	C15—O2—C11—C12	−177.12 (14)
C3—C4—C5—N1	0.2 (2)	C16—O3—C12—C13	−1.9 (2)
C6—C4—C5—N1	−179.40 (15)	C16—O3—C12—C11	177.32 (14)
C5—C4—C6—O1	176.30 (15)	C10—C11—C12—O3	−179.61 (14)
C3—C4—C6—O1	−3.3 (2)	O2—C11—C12—O3	0.4 (2)
C5—C4—C6—C7	−3.6 (2)	C10—C11—C12—C13	−0.3 (2)
C3—C4—C6—C7	176.84 (14)	O2—C11—C12—C13	179.69 (14)
O1—C6—C7—C8	3.0 (2)	O3—C12—C13—C14	−179.96 (14)
C4—C6—C7—C8	−177.10 (14)	C11—C12—C13—C14	0.8 (2)
C6—C7—C8—C9	−179.94 (14)	C12—C13—C14—C9	−1.1 (2)
C7—C8—C9—C14	173.53 (15)	C10—C9—C14—C13	0.8 (2)
C7—C8—C9—C10	−5.9 (3)	C8—C9—C14—C13	−178.66 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H11···N1	0.83 (1)	2.05 (1)	2.857 (2)	163 (2)
O1W—H12···O1Wⁱ	0.85 (1)	1.94 (3)	2.763 (2)	162 (7)

Symmetry code: (i) −x+3/2, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₅NO₃·H₂O
M_r	287.31
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	100
a, b, c (Å)	17.9809 (4), 4.5004 (1), 18.2230 (4)
β (°)	101.775 (2)
V (Å³)	1443.60 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.20 × 0.15 × 0.10

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	12630, 3315, 2362
R_int	0.041
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.126, 1.02
No. of reflections	3315
No. of parameters	200
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.52, −0.20

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H11···N1	0.83 (1)	2.05 (1)	2.857 (2)	163 (2)
O1W—H12···O1Wⁱ	0.85 (1)	1.94 (3)	2.763 (2)	162 (7)

Symmetry code: (i) −x+3/2, y−1/2, −z+1/2.

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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