3-Phenyl-1-(pyrrol-2-yl)prop-2-en-1-one.

The title mol-ecule, C(13)H(11)NO, is almost flat, the angle between the pyrrole and the phenyl rings being 10.9 (1)°. The atoms of the central C(3)O unit are coplanar, with a mean deviation from the plane of 0.001 (1) Å. The angles between this plane and the pyrrole and phenyl rings are 3.3 (1) and 8.0 (1)°, respectively. The mol-ecules form centrosymmetric dimers through a pair of N-H⋯O hydrogen bonds with an R(2) (2)(10) motif.

Related literature

For details of the biological and the pharmaceutical properties of chalcones, see: Chen et al. (1999 ▶); Dimmock et al. (1999 ▶); Go et al. (2005 ▶); Lin et al. (2002 ▶); Lunardi et al. (2003 ▶); Opletalova (2000 ▶). For other related literature, see: Gong & Shen (2007 ▶); Kumaran et al. (1996 ▶); Shanmuga Sundara Raj et al. (1997 ▶, 1998 ▶). For a description of hydrogen-bond motifs, see: Etter et al. (1990 ▶).

Experimental

Crystal data

C13H11NO

M = 197.23

Monoclinic,

a = 19.848 (4) Å

b = 5.6435 (12) Å

c = 19.325 (4) Å

β = 101.535 (4)°

V = 2120.9 (8) Å3

Z = 8

Mo Kα radiation

μ = 0.08 mm−1

T = 293 (2) K

0.34 × 0.13 × 0.11 mm

Data collection

Bruker APEX area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.974, T max = 0.991

5274 measured reflections

2069 independent reflections

1164 reflections with I > 2σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.137

S = 1.00

2069 reflections

136 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, 1990 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: SHELXTL (Bruker, 2002 ▶); software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807063489/fb2072sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807063489/fb2072Isup2.hkl

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

C13H11NO	F000 = 832
Mr = 197.23	Dx = 1.235 Mg m−3
Monoclinic, C2/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 642 reflections
a = 19.848 (4) Å	θ = 2.7–24.7º
b = 5.6435 (12) Å	µ = 0.08 mm−1
c = 19.325 (4) Å	T = 293 (2) K
β = 101.535 (4)º	Prism, light yellow
V = 2120.9 (8) Å3	0.34 × 0.13 × 0.11 mm
Z = 8

Bruker APEX area-detector diffractometer	2069 independent reflections
Radiation source: fine-focus sealed tube	1164 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.040
T = 293(2) K	θmax = 26.0º
φ and ω scans	θmin = 2.1º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −24→23
Tmin = 0.974, Tmax = 0.991	k = −6→6
5274 measured reflections	l = −14→23

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.054	H-atom parameters constrained
wR(F2) = 0.137	w = 1/[σ2(Fo2) + (0.0534P)2 + 0.0616P] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max < 0.001
2069 reflections	Δρmax = 0.13 e Å−3
136 parameters	Δρmin = −0.13 e Å−3
44 constraints	Extinction correction: none
Primary atom site location: structure-invariant direct methods

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.

	x	y	z	Uiso*/Ueq
O1	0.54821 (8)	0.1673 (3)	0.58099 (8)	0.0776 (5)
N1	0.41400 (9)	0.2050 (3)	0.50060 (9)	0.0635 (5)
H1	0.4349	0.0847	0.4874	0.076*
C1	0.44232 (11)	0.3625 (4)	0.55205 (10)	0.0547 (6)
C2	0.39177 (12)	0.5253 (4)	0.55675 (12)	0.0673 (7)
H2	0.3961	0.6536	0.5875	0.081*
C3	0.33346 (12)	0.4656 (4)	0.50787 (13)	0.0762 (7)
H3	0.2916	0.5456	0.4997	0.091*
C4	0.34890 (12)	0.2665 (4)	0.47383 (12)	0.0724 (7)
H4	0.3191	0.1871	0.4380	0.087*
C5	0.51165 (12)	0.3362 (4)	0.59096 (11)	0.0586 (6)
C6	0.53729 (12)	0.5178 (4)	0.64459 (11)	0.0640 (6)
H6	0.5083	0.6427	0.6503	0.077*
C7	0.59949 (12)	0.5118 (4)	0.68497 (11)	0.0609 (6)
H7	0.6274	0.3860	0.6775	0.073*
C8	0.62940 (11)	0.6813 (4)	0.74025 (10)	0.0564 (6)
C9	0.69227 (11)	0.6324 (4)	0.78395 (11)	0.0645 (6)
H9	0.7159	0.4953	0.7767	0.077*
C10	0.72018 (13)	0.7842 (5)	0.83802 (13)	0.0733 (7)
H10	0.7622	0.7486	0.8671	0.088*
C11	0.68593 (15)	0.9879 (5)	0.84886 (13)	0.0780 (8)
H11	0.7046	1.0898	0.8855	0.094*
C12	0.62420 (14)	1.0411 (4)	0.80554 (13)	0.0782 (7)
H12	0.6011	1.1794	0.8128	0.094*
C13	0.59620 (13)	0.8898 (4)	0.75115 (12)	0.0699 (7)
H13	0.5547	0.9283	0.7216	0.084*

	U11	U22	U33	U12	U13	U23
O1	0.0839 (12)	0.0726 (11)	0.0687 (11)	0.0236 (9)	−0.0030 (8)	−0.0209 (8)
N1	0.0670 (12)	0.0654 (12)	0.0563 (11)	0.0096 (10)	0.0076 (9)	−0.0115 (10)
C1	0.0643 (14)	0.0543 (14)	0.0453 (12)	0.0030 (11)	0.0102 (11)	−0.0051 (11)
C2	0.0730 (15)	0.0639 (16)	0.0651 (15)	0.0084 (13)	0.0138 (13)	−0.0107 (12)
C3	0.0672 (15)	0.0833 (18)	0.0767 (17)	0.0166 (14)	0.0114 (14)	−0.0072 (14)
C4	0.0619 (15)	0.0858 (18)	0.0661 (15)	0.0029 (14)	0.0051 (12)	−0.0102 (14)
C5	0.0749 (16)	0.0527 (14)	0.0486 (13)	0.0075 (12)	0.0134 (11)	−0.0024 (11)
C6	0.0732 (15)	0.0575 (15)	0.0609 (14)	0.0051 (12)	0.0123 (12)	−0.0109 (11)
C7	0.0684 (14)	0.0583 (15)	0.0579 (14)	0.0009 (12)	0.0174 (12)	−0.0049 (11)
C8	0.0646 (14)	0.0539 (14)	0.0521 (13)	−0.0081 (12)	0.0154 (11)	−0.0037 (11)
C9	0.0660 (15)	0.0655 (15)	0.0631 (15)	−0.0076 (12)	0.0157 (12)	−0.0018 (12)
C10	0.0717 (16)	0.0802 (18)	0.0669 (16)	−0.0221 (15)	0.0110 (12)	−0.0012 (14)
C11	0.104 (2)	0.0711 (19)	0.0591 (15)	−0.0342 (16)	0.0157 (15)	−0.0060 (13)
C12	0.108 (2)	0.0550 (15)	0.0728 (18)	−0.0107 (15)	0.0210 (16)	−0.0106 (13)
C13	0.0828 (16)	0.0579 (14)	0.0672 (16)	−0.0021 (13)	0.0105 (13)	−0.0049 (12)

O1—C5	1.236 (2)	C7—C8	1.468 (3)
N1—C4	1.338 (3)	C7—H7	0.9300
N1—C1	1.368 (2)	C8—C13	1.385 (3)
N1—H1	0.8600	C8—C9	1.387 (3)
C1—C2	1.377 (3)	C9—C10	1.379 (3)
C1—C5	1.438 (3)	C9—H9	0.9300
C2—C3	1.381 (3)	C10—C11	1.373 (3)
C2—H2	0.9300	C10—H10	0.9300
C3—C4	1.367 (3)	C11—C12	1.372 (3)
C3—H3	0.9300	C11—H11	0.9300
C4—H4	0.9300	C12—C13	1.382 (3)
C5—C6	1.474 (3)	C12—H12	0.9300
C6—C7	1.322 (3)	C13—H13	0.9300
C6—H6	0.9300
C4—N1—C1	109.70 (18)	C6—C7—C8	127.4 (2)
C4—N1—H1	125.2	C6—C7—H7	116.3
C1—N1—H1	125.2	C8—C7—H7	116.3
N1—C1—C2	106.42 (18)	C13—C8—C9	118.3 (2)
N1—C1—C5	121.59 (19)	C13—C8—C7	121.9 (2)
C2—C1—C5	132.0 (2)	C9—C8—C7	119.8 (2)
C1—C2—C3	108.3 (2)	C10—C9—C8	120.9 (2)
C1—C2—H2	125.8	C10—C9—H9	119.5
C3—C2—H2	125.8	C8—C9—H9	119.5
C4—C3—C2	107.0 (2)	C11—C10—C9	120.0 (2)
C4—C3—H3	126.5	C11—C10—H10	120.0
C2—C3—H3	126.5	C9—C10—H10	120.0
N1—C4—C3	108.6 (2)	C12—C11—C10	119.9 (2)
N1—C4—H4	125.7	C12—C11—H11	120.0
C3—C4—H4	125.7	C10—C11—H11	120.0
O1—C5—C1	121.92 (19)	C11—C12—C13	120.2 (3)
O1—C5—C6	121.0 (2)	C11—C12—H12	119.9
C1—C5—C6	117.1 (2)	C13—C12—H12	119.9
C7—C6—C5	123.2 (2)	C12—C13—C8	120.6 (2)
C7—C6—H6	118.4	C12—C13—H13	119.7
C5—C6—H6	118.4	C8—C13—H13	119.7
C4—N1—C1—C2	0.4 (2)	C1—C5—C6—C7	178.6 (2)
C4—N1—C1—C5	178.7 (2)	C5—C6—C7—C8	−179.1 (2)
N1—C1—C2—C3	−0.3 (3)	C6—C7—C8—C13	−7.4 (3)
C5—C1—C2—C3	−178.3 (2)	C6—C7—C8—C9	171.7 (2)
C1—C2—C3—C4	0.1 (3)	C13—C8—C9—C10	1.6 (3)
C1—N1—C4—C3	−0.3 (3)	C7—C8—C9—C10	−177.45 (19)
C2—C3—C4—N1	0.2 (3)	C8—C9—C10—C11	−0.5 (3)
N1—C1—C5—O1	−1.8 (3)	C9—C10—C11—C12	−0.5 (4)
C2—C1—C5—O1	175.9 (2)	C10—C11—C12—C13	0.2 (4)
N1—C1—C5—C6	179.22 (18)	C11—C12—C13—C8	1.0 (4)
C2—C1—C5—C6	−3.0 (4)	C9—C8—C13—C12	−1.9 (3)
O1—C5—C6—C7	−0.4 (3)	C7—C8—C13—C12	177.2 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.86	2.02	2.817 (2)	155
C7—H7···O1	0.93	2.51	2.835 (3)	101

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.86	2.02	2.817 (2)	155
C7—H7⋯O1	0.93	2.51	2.835 (3)	101

Symmetry code: (i) .