3-(4-Methoxy­phen­yl)-1-(2-pyrrol­yl)prop-2-en-1-one

Li, D.-Q.

doi:10.1107/S160053680802864X

organic compounds

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Volume 64| Part 10| October 2008| Page o1920

doi:10.1107/S160053680802864X

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3-(4-Methoxyphenyl)-1-(2-pyrrolyl)prop-2-en-1-one

Dong-Qing Li ^a ^*

^aDepartment of Chemistry and Biology, Yulin Normal University, Guangxi 537000, People's Republic of China
^*Correspondence e-mail: ldq00000@126.com

(Received 18 July 2008; accepted 7 September 2008; online 13 September 2008)

The title molecule, C₁₄H₁₃NO₂, is almost flat with a dihedral angle of 8.0 (1)° between the pyrrole and benzene rings. The central C₃O ketone unit has an s-cis conformation and is also coplanar with a torsion angle of −0.6 (3) °. An intramolecular C—H⋯O hydrogen bond generates an S(5) ring motif. In addition, the methoxy group is coplanar with the attached benzene ring. In the crystal structure, neighboring molecules are paired through N—H⋯O hydrogen bonds into centrosymmetric dimers with an R²₂(10) motif.

Related literature

For the pharmaceutical and biological properties of chalcones, see: Lin et al. (2002 ); Modzelewska et al. (2006 ); Opletalova (2000 ); Opletalova & Sedivy (1999 ); Sogawa et al. (1994 ). For chalcones as non-linear optical materials, see: Agrinskaya et al. (1999 ); Indira et al. (2002 ). For related structures, see: Bukhari et al. (2008 ); Fun et al. (2008 ); Gong, et al. (2008 ).

Experimental

Crystal data

C₁₄H₁₃NO₂
M_r = 227.25
Monoclinic, P 2₁ /c
a = 5.0815 (7) Å
b = 17.172 (3) Å
c = 13.973 (2) Å
β = 97.878 (3)°
V = 1207.8 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 293 (2) K
0.40 × 0.24 × 0.20 mm

Data collection

Bruker SMART APEX area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.967, T_max = 0.988
5842 measured reflections
2369 independent reflections
1809 reflections with I > 2σ(I)
R_int = 0.019

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.124
S = 1.05
2369 reflections
155 parameters
H-atom parameters constrained
Δρ_max = 0.13 e Å⁻³
Δρ_min = −0.13 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7⋯O1	0.93	2.52	2.838 (2)	100
N1—H1⋯O1ⁱ	0.86	2.03	2.8314 (17)	155
Symmetry code: (i) -x, -y+1, -z+1.

Data collection: SMART (Bruker, 2002 ); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680802864X/cs2091sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680802864X/cs2091Isup2.hkl

checkCIF report

Comment top

Chalcone derivatives have recently attracted extensive interest due to possessing a wide variety of pharmaceutical (Lin et al., 2002; Modzelewska et al., 2006; Sogawa et al., 1994) and biological properties (Opletalova, 2000; Opletalova & Sedivy, 1999). Some substituted chalcones also exhibit the potential applications as non-linear optical materials (Agrinskaya et al., 1999; Indira et al., 2002). Considering the importance of these types of compounds, a new chalcone compound was synthesized and its crystal structure is reported here.

The molecular structure of the title molecule (Fig. 1) is almost planar as indicated by a dihedral angle of 8.0 (1) ° between the pyrrole and benzene rings. The central O1/C5/C6/C7 ketone motif exhibits an s-cis conformation as usual in other related chalcone derivatives (Bukhari et al., 2008; Fun et al., 2008; Gong, et al., 2008;) and also coplanar with a torsion angle of -0.6 (3) °, meanwhile, O1 atom acts as an acceptor and is involved in an intramolecular C—H···O hydrogen bond (Table 1) to generate an S(5) ring motif. In the crystal packing, the compound can be stabilized by intermolecular N—H···O hydrogen bonds with –NH groups as donors to form centrosymmetric dimers with an R²₂(10) motif as shown in Fig. 2.

Related literature top

For the pharmaceutical and biological properties of chalcones, see: Lin et al. (2002); Modzelewska et al. (2006); Opletalova (2000); Opletalova & Sedivy (1999); Sogawa et al. (1994). For chalcones as non-linear optical materials, see: Agrinskaya et al. (1999); Indira et al. (2002). For other related literature, see: (Bukhari et al. (2008); Fun et al. (2008); Gong, et al. (2008).

Experimental top

The title compound was synthesized by the condensation of 2-acetylpyrrole (1.09 g, 10.0 mmol) and 4-methoxybenzaldehyde (1.06 g, 5.0 mmol) in methanol (30 ml) and ammonia (25%, 25 ml) in the presence of sodium hydroxide (0.56 g, 10 mmol). After refluxed at 358 K for 8 h, the contents of the flask were cooled to give a yellow crude precipitate which was separated by filtration, washed with water and iced ethanol. Recrystallization from ethanol afforded yellow prism-like crystals. Yield: 0.85 g (74.8%).

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound with displacement ellipsoids drawn at the 30% probability level and H atoms as spheres of arbitrary radius.
	Fig. 2. Packing diagram of the title structure showing the N—H···.O hydrogen bonding interactions.

3-(4-Methoxyphenyl)-1-(2-pyrrolyl)prop-2-en-1-one top

Crystal data top

C₁₄H₁₃NO₂	F(000) = 480
M_r = 227.25	D_x = 1.250 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1716 reflections
a = 5.0815 (7) Å	θ = 2.4–25.8°
b = 17.172 (3) Å	µ = 0.08 mm⁻¹
c = 13.973 (2) Å	T = 293 K
β = 97.878 (3)°	Prism, yellow
V = 1207.8 (3) Å³	0.40 × 0.24 × 0.20 mm
Z = 4

Data collection top

Bruker APEX area-detector diffractometer	2369 independent reflections
Radiation source: fine-focus sealed tube	1809 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.020
ϕ and ω scans	θ_max = 26.0°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −6→5
T_min = 0.967, T_max = 0.988	k = −20→21
5842 measured reflections	l = −14→17

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.124	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0557P)² + 0.1497P] where P = (F_o² + 2F_c²)/3
2369 reflections	(Δ/σ)_max < 0.001
155 parameters	Δρ_max = 0.13 e Å⁻³
0 restraints	Δρ_min = −0.13 e Å⁻³

Crystal data top

C₁₄H₁₃NO₂	V = 1207.8 (3) Å³
M_r = 227.25	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 5.0815 (7) Å	µ = 0.08 mm⁻¹
b = 17.172 (3) Å	T = 293 K
c = 13.973 (2) Å	0.40 × 0.24 × 0.20 mm
β = 97.878 (3)°

Data collection top

Bruker APEX area-detector diffractometer	2369 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1809 reflections with I > 2σ(I)
T_min = 0.967, T_max = 0.988	R_int = 0.020
5842 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.124	H-atom parameters constrained
S = 1.05	Δρ_max = 0.13 e Å⁻³
2369 reflections	Δρ_min = −0.13 e Å⁻³
155 parameters

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

	x	y	z	U_iso*/U_eq
N1	−0.2188 (3)	0.56328 (8)	0.38761 (9)	0.0567 (4)
H1	−0.1976	0.5437	0.4448	0.068*
O1	0.1957 (3)	0.45435 (7)	0.40994 (8)	0.0707 (4)
O2	0.9171 (3)	0.29580 (8)	−0.06480 (9)	0.0769 (4)
C1	−0.0745 (3)	0.54326 (9)	0.31541 (10)	0.0520 (4)
C2	−0.1690 (4)	0.58892 (10)	0.23690 (12)	0.0634 (5)
H2	−0.1082	0.5885	0.1771	0.076*
C3	−0.3705 (4)	0.63554 (11)	0.26280 (13)	0.0707 (5)
H3	−0.4688	0.6721	0.2238	0.085*
C4	−0.3978 (3)	0.61792 (11)	0.35599 (12)	0.0634 (5)
H4	−0.5202	0.6401	0.3916	0.076*
C5	0.1294 (3)	0.48406 (9)	0.32984 (11)	0.0535 (4)
C6	0.2491 (3)	0.45958 (10)	0.24510 (11)	0.0570 (4)
H6	0.1913	0.4834	0.1862	0.068*
C7	0.4347 (3)	0.40549 (10)	0.24796 (11)	0.0556 (4)
H7	0.4909	0.3835	0.3081	0.067*
C8	0.5616 (3)	0.37631 (9)	0.16757 (11)	0.0517 (4)
C9	0.7403 (3)	0.31532 (10)	0.17995 (11)	0.0578 (4)
H9	0.7789	0.2930	0.2409	0.069*
C10	0.8645 (3)	0.28594 (10)	0.10527 (12)	0.0586 (4)
H10	0.9827	0.2445	0.1160	0.070*
C11	0.8105 (3)	0.31894 (10)	0.01503 (11)	0.0563 (4)
C12	0.6337 (4)	0.38052 (11)	0.00062 (12)	0.0714 (5)
H12	0.5978	0.4033	−0.0602	0.086*
C13	0.5110 (4)	0.40830 (11)	0.07518 (12)	0.0669 (5)
H13	0.3915	0.4494	0.0639	0.080*
C14	1.0982 (4)	0.23244 (12)	−0.05485 (15)	0.0873 (6)
H14A	1.2445	0.2445	−0.0060	0.131*
H14B	1.1631	0.2235	−0.1153	0.131*
H14C	1.0094	0.1866	−0.0365	0.131*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0611 (8)	0.0626 (9)	0.0479 (7)	−0.0046 (7)	0.0129 (6)	−0.0043 (6)
O1	0.0880 (9)	0.0760 (8)	0.0520 (7)	0.0121 (7)	0.0233 (6)	0.0115 (6)
O2	0.0977 (9)	0.0780 (9)	0.0577 (7)	0.0310 (7)	0.0207 (7)	0.0018 (6)
C1	0.0533 (9)	0.0579 (10)	0.0459 (8)	−0.0089 (7)	0.0107 (7)	−0.0036 (7)
C2	0.0698 (11)	0.0717 (12)	0.0499 (9)	0.0006 (9)	0.0120 (8)	0.0007 (8)
C3	0.0771 (12)	0.0731 (12)	0.0605 (11)	0.0098 (10)	0.0042 (9)	0.0001 (9)
C4	0.0606 (10)	0.0670 (11)	0.0630 (10)	0.0017 (9)	0.0098 (8)	−0.0132 (9)
C5	0.0581 (9)	0.0570 (10)	0.0468 (8)	−0.0110 (8)	0.0120 (7)	0.0004 (7)
C6	0.0610 (10)	0.0631 (10)	0.0480 (8)	−0.0034 (8)	0.0112 (7)	0.0020 (7)
C7	0.0607 (10)	0.0594 (10)	0.0473 (8)	−0.0088 (8)	0.0097 (7)	0.0029 (7)
C8	0.0562 (9)	0.0501 (9)	0.0492 (8)	−0.0053 (7)	0.0084 (7)	0.0006 (7)
C9	0.0609 (10)	0.0617 (11)	0.0499 (9)	0.0015 (8)	0.0049 (8)	0.0112 (7)
C10	0.0583 (10)	0.0567 (10)	0.0604 (10)	0.0089 (8)	0.0062 (8)	0.0056 (8)
C11	0.0636 (10)	0.0549 (10)	0.0507 (9)	0.0046 (8)	0.0096 (8)	−0.0014 (7)
C12	0.0972 (14)	0.0701 (12)	0.0473 (9)	0.0254 (11)	0.0115 (9)	0.0082 (8)
C13	0.0855 (13)	0.0608 (11)	0.0553 (10)	0.0232 (9)	0.0137 (9)	0.0050 (8)
C14	0.1013 (15)	0.0851 (14)	0.0779 (13)	0.0345 (13)	0.0212 (11)	−0.0047 (11)

Geometric parameters (Å, º) top

N1—C4	1.339 (2)	C7—C8	1.459 (2)
N1—C1	1.3699 (19)	C7—H7	0.9300
N1—H1	0.8600	C8—C9	1.382 (2)
O1—C5	1.2342 (18)	C8—C13	1.394 (2)
O2—C11	1.3644 (19)	C9—C10	1.386 (2)
O2—C14	1.419 (2)	C9—H9	0.9300
C1—C2	1.380 (2)	C10—C11	1.375 (2)
C1—C5	1.446 (2)	C10—H10	0.9300
C2—C3	1.386 (2)	C11—C12	1.384 (2)
C2—H2	0.9300	C12—C13	1.371 (2)
C3—C4	1.362 (2)	C12—H12	0.9300
C3—H3	0.9300	C13—H13	0.9300
C4—H4	0.9300	C14—H14A	0.9600
C5—C6	1.465 (2)	C14—H14B	0.9600
C6—C7	1.320 (2)	C14—H14C	0.9600
C6—H6	0.9300

C4—N1—C1	109.93 (14)	C9—C8—C13	116.70 (15)
C4—N1—H1	125.0	C9—C8—C7	121.10 (14)
C1—N1—H1	125.0	C13—C8—C7	122.20 (15)
C11—O2—C14	117.91 (14)	C8—C9—C10	122.74 (15)
N1—C1—C2	106.24 (15)	C8—C9—H9	118.6
N1—C1—C5	121.30 (14)	C10—C9—H9	118.6
C2—C1—C5	132.46 (15)	C11—C10—C9	119.07 (15)
C1—C2—C3	108.04 (15)	C11—C10—H10	120.5
C1—C2—H2	126.0	C9—C10—H10	120.5
C3—C2—H2	126.0	O2—C11—C10	125.29 (15)
C4—C3—C2	107.26 (17)	O2—C11—C12	115.23 (14)
C4—C3—H3	126.4	C10—C11—C12	119.48 (15)
C2—C3—H3	126.4	C13—C12—C11	120.59 (16)
N1—C4—C3	108.52 (15)	C13—C12—H12	119.7
N1—C4—H4	125.7	C11—C12—H12	119.7
C3—C4—H4	125.7	C12—C13—C8	121.42 (16)
O1—C5—C1	121.24 (14)	C12—C13—H13	119.3
O1—C5—C6	121.48 (16)	C8—C13—H13	119.3
C1—C5—C6	117.27 (14)	O2—C14—H14A	109.5
C7—C6—C5	123.47 (15)	O2—C14—H14B	109.5
C7—C6—H6	118.3	H14A—C14—H14B	109.5
C5—C6—H6	118.3	O2—C14—H14C	109.5
C6—C7—C8	127.43 (15)	H14A—C14—H14C	109.5
C6—C7—H7	116.3	H14B—C14—H14C	109.5
C8—C7—H7	116.3

C4—N1—C1—C2	0.86 (18)	C6—C7—C8—C9	−175.31 (17)
C4—N1—C1—C5	−178.71 (14)	C6—C7—C8—C13	5.0 (3)
N1—C1—C2—C3	−0.38 (19)	C13—C8—C9—C10	−0.4 (3)
C5—C1—C2—C3	179.11 (17)	C7—C8—C9—C10	179.89 (15)
C1—C2—C3—C4	−0.2 (2)	C8—C9—C10—C11	0.6 (3)
C1—N1—C4—C3	−1.01 (19)	C14—O2—C11—C10	0.2 (3)
C2—C3—C4—N1	0.7 (2)	C14—O2—C11—C12	−179.46 (18)
N1—C1—C5—O1	−6.2 (2)	C9—C10—C11—O2	−179.72 (16)
C2—C1—C5—O1	174.32 (17)	C9—C10—C11—C12	−0.1 (3)
N1—C1—C5—C6	172.35 (14)	O2—C11—C12—C13	179.16 (17)
C2—C1—C5—C6	−7.1 (3)	C10—C11—C12—C13	−0.5 (3)
O1—C5—C6—C7	−0.6 (3)	C11—C12—C13—C8	0.6 (3)
C1—C5—C6—C7	−179.16 (15)	C9—C8—C13—C12	−0.2 (3)
C5—C6—C7—C8	178.75 (15)	C7—C8—C13—C12	179.49 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O1	0.93	2.52	2.838 (2)	100
N1—H1···O1ⁱ	0.86	2.03	2.8314 (17)	155

Symmetry code: (i) −x, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₃NO₂
M_r	227.25
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	5.0815 (7), 17.172 (3), 13.973 (2)
β (°)	97.878 (3)
V (Å³)	1207.8 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.40 × 0.24 × 0.20

Data collection
Diffractometer	Bruker APEX area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.967, 0.988
No. of measured, independent and observed [I > 2σ(I)] reflections	5842, 2369, 1809
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.124, 1.05
No. of reflections	2369
No. of parameters	155
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.13, −0.13

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O1	0.93	2.52	2.838 (2)	100.4
N1—H1···O1ⁱ	0.86	2.03	2.8314 (17)	154.9

Symmetry code: (i) −x, −y+1, −z+1.

Acknowledgements

The authors thank Yulin Normal University for supporting this study.

References

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