3-(4-Methoxy-phen-yl)-1-(2-pyrrol-yl)prop-2-en-1-one.

The title mol-ecule, C(14)H(13)NO(2), is almost flat with a dihedral angle of 8.0 (1)° between the pyrrole and benzene rings. The central C(3)O ketone unit has an s-cis conformation and is also coplanar with a torsion angle of -0.6 (3) °. An intra-molecular C-H⋯O hydrogen bond generates an S(5) ring motif. In addition, the meth-oxy group is coplanar with the attached benzene ring. In the crystal structure, neighboring mol-ecules are paired through N-H⋯O hydrogen bonds into centrosymmetric dimers with an R(2) (2)(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 = 227.25

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.124

S = 1.05

2369 reflections

155 parameters

H-atom parameters constrained

Δρmax = 0.13 e Å−3

Δρmin = −0.13 e Å−3

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.

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

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

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

C14H13NO2	F(000) = 480
Mr = 227.25	Dx = 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

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

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(Fo2) + (0.0557P)2 + 0.1497P] where P = (Fo2 + 2Fc2)/3
2369 reflections	(Δ/σ)max < 0.001
155 parameters	Δρmax = 0.13 e Å−3
0 restraints	Δρmin = −0.13 e Å−3

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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.

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) .