(E)-3-(1-Methyl-1H-pyrrol-2-yl)-1-phenyl-prop-2-en-1-one.

The crystal structure of the title compound, C(14)H(13)NO, exhibits an E configuration. The conjugated compound is slightly twisted with a dihedral angle of 29.3° between the benzene and pyrrole rings. Two inter-molecular C-H⋯O inter-actions lead to a dimer. In the crystal, intermolecular C-H⋯O interactions generate an inversion dimer.

Related literature

For related literature on chalcone and its derivatives, see: Kelly et al. (2004 ▶); Takahashi et al. (2005 ▶). For the anti­cancer properties of chalcone derivatives, see: Zi & Simoneau (2005 ▶); Bennasroune et al. (2004 ▶); Moriarty et al. (2006 ▶). For a related structure, see Jing (2009 ▶).

Experimental

Crystal data

C14H13NO

M = 211.25

Monoclinic,

a = 13.209 (2) Å

b = 4.8849 (9) Å

c = 18.036 (3) Å

β = 102.394 (4)°

V = 1136.6 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 296 K

0.25 × 0.22 × 0.20 mm

Data collection

Bruker APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.981, T max = 0.985

5920 measured reflections

1996 independent reflections

1459 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.153

S = 1.00

1996 reflections

146 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.12 e Å−3

Δρmin = −0.19 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); 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/S1600536811009214/fl2335sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811009214/fl2335Isup2.hkl

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

C14H13NO	F(000) = 448
Mr = 211.25	Dx = 1.235 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1712 reflections
a = 13.209 (2) Å	θ = 2.3–27.0°
b = 4.8849 (9) Å	µ = 0.08 mm−1
c = 18.036 (3) Å	T = 296 K
β = 102.394 (4)°	Prism, yellow
V = 1136.6 (4) Å3	0.25 × 0.22 × 0.20 mm
Z = 4

Bruker APEXII CCD diffractometer	1996 independent reflections
Radiation source: fine-focus sealed tube	1459 reflections with I > 2σ(I)
graphite	Rint = 0.036
φ and ω scans	θmax = 25.0°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −14→15
Tmin = 0.981, Tmax = 0.985	k = −5→5
5920 measured reflections	l = −21→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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.153	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.1P)2 + 0.038P] where P = (Fo2 + 2Fc2)/3
1996 reflections	(Δ/σ)max < 0.001
146 parameters	Δρmax = 0.12 e Å−3
1 restraint	Δρmin = −0.19 e Å−3

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
C1	0.49092 (14)	0.6200 (4)	0.10561 (11)	0.0666 (5)
H1A	0.5321	0.7628	0.1338	0.100*
H1B	0.4586	0.6867	0.0561	0.100*
H1C	0.5345	0.4668	0.1006	0.100*
C2	0.39810 (16)	0.6409 (4)	0.21180 (10)	0.0628 (5)
H2	0.4367	0.7835	0.2380	0.075*
C3	0.31956 (16)	0.5074 (4)	0.23440 (11)	0.0671 (5)
H3	0.2954	0.5409	0.2783	0.080*
C4	0.28227 (14)	0.3116 (4)	0.17956 (10)	0.0599 (5)
H4	0.2286	0.1892	0.1804	0.072*
C5	0.33895 (13)	0.3300 (3)	0.12319 (9)	0.0497 (4)
C6	0.33082 (14)	0.1826 (3)	0.05417 (9)	0.0528 (5)
H6	0.3806	0.2200	0.0261	0.063*
C7	0.25918 (14)	−0.0039 (4)	0.02554 (10)	0.0555 (5)
H7	0.2072	−0.0442	0.0514	0.067*
C8	0.26049 (14)	−0.1460 (3)	−0.04539 (9)	0.0533 (5)
C9	0.16992 (13)	−0.3136 (3)	−0.08205 (9)	0.0522 (5)
C10	0.07359 (15)	−0.2885 (4)	−0.06423 (11)	0.0693 (6)
H10	0.0645	−0.1675	−0.0264	0.083*
C11	−0.00986 (17)	−0.4435 (5)	−0.10267 (13)	0.0820 (6)
H11	−0.0748	−0.4233	−0.0911	0.098*
C12	0.00353 (19)	−0.6241 (5)	−0.15709 (13)	0.0828 (7)
H12	−0.0520	−0.7295	−0.1820	0.099*
C13	0.0988 (2)	−0.6518 (4)	−0.17544 (13)	0.0791 (6)
H13	0.1074	−0.7752	−0.2128	0.095*
C14	0.18079 (16)	−0.4978 (4)	−0.13874 (10)	0.0636 (5)
H14	0.2448	−0.5164	−0.1518	0.076*
N1	0.41137 (10)	0.5347 (3)	0.14553 (7)	0.0526 (4)
O1	0.33614 (10)	−0.1304 (3)	−0.07478 (7)	0.0721 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0590 (11)	0.0738 (12)	0.0670 (12)	−0.0017 (10)	0.0131 (9)	−0.0013 (10)
C2	0.0711 (12)	0.0597 (11)	0.0545 (10)	0.0080 (9)	0.0067 (9)	−0.0111 (9)
C3	0.0788 (13)	0.0739 (12)	0.0514 (11)	0.0111 (10)	0.0204 (9)	−0.0058 (9)
C4	0.0664 (11)	0.0655 (11)	0.0496 (10)	0.0013 (9)	0.0164 (8)	0.0008 (8)
C5	0.0557 (10)	0.0477 (9)	0.0449 (9)	0.0075 (8)	0.0091 (7)	0.0017 (7)
C6	0.0621 (10)	0.0502 (9)	0.0477 (9)	0.0061 (8)	0.0152 (8)	0.0039 (7)
C7	0.0610 (11)	0.0597 (10)	0.0471 (9)	0.0040 (8)	0.0149 (8)	0.0000 (8)
C8	0.0607 (10)	0.0529 (10)	0.0468 (9)	0.0049 (8)	0.0126 (8)	0.0016 (7)
C9	0.0605 (11)	0.0487 (9)	0.0460 (9)	0.0056 (8)	0.0082 (7)	0.0069 (7)
C10	0.0669 (12)	0.0757 (12)	0.0644 (12)	0.0061 (10)	0.0120 (9)	−0.0022 (10)
C11	0.0627 (13)	0.0969 (15)	0.0819 (15)	−0.0026 (12)	0.0056 (11)	0.0084 (13)
C12	0.0885 (16)	0.0747 (14)	0.0731 (14)	−0.0180 (12)	−0.0095 (12)	0.0096 (11)
C13	0.0952 (16)	0.0692 (13)	0.0691 (13)	−0.0103 (12)	0.0090 (12)	−0.0103 (10)
C14	0.0760 (13)	0.0622 (11)	0.0505 (10)	0.0003 (9)	0.0085 (9)	−0.0053 (8)
N1	0.0548 (9)	0.0533 (8)	0.0483 (8)	0.0064 (7)	0.0081 (6)	0.0003 (6)
O1	0.0733 (9)	0.0885 (10)	0.0591 (8)	−0.0093 (7)	0.0244 (7)	−0.0155 (7)

C1—N1	1.456 (2)	C7—C8	1.459 (2)
C1—H1A	0.9600	C7—H7	0.9300
C1—H1B	0.9600	C8—O1	1.2298 (19)
C1—H1C	0.9600	C8—C9	1.483 (2)
C2—N1	1.349 (2)	C9—C10	1.383 (2)
C2—C3	1.360 (3)	C9—C14	1.392 (2)
C2—H2	0.9300	C10—C11	1.393 (3)
C3—C4	1.388 (3)	C10—H10	0.9300
C3—H3	0.9300	C11—C12	1.359 (3)
C4—C5	1.389 (2)	C11—H11	0.9300
C4—H4	0.9300	C12—C13	1.375 (3)
C5—N1	1.383 (2)	C12—H12	0.9300
C5—C6	1.422 (2)	C13—C14	1.367 (3)
C6—C7	1.335 (2)	C13—H13	0.9300
C6—H6	0.9300	C14—H14	0.9300
N1—C1—H1A	109.5	O1—C8—C7	120.81 (16)
N1—C1—H1B	109.5	O1—C8—C9	119.64 (15)
H1A—C1—H1B	109.5	C7—C8—C9	119.56 (16)
N1—C1—H1C	109.5	C10—C9—C14	118.22 (17)
H1A—C1—H1C	109.5	C10—C9—C8	122.82 (16)
H1B—C1—H1C	109.5	C14—C9—C8	118.92 (16)
N1—C2—C3	109.48 (17)	C9—C10—C11	120.35 (19)
N1—C2—H2	125.3	C9—C10—H10	119.8
C3—C2—H2	125.3	C11—C10—H10	119.8
C2—C3—C4	107.09 (17)	C12—C11—C10	120.0 (2)
C2—C3—H3	126.5	C12—C11—H11	120.0
C4—C3—H3	126.5	C10—C11—H11	120.0
C3—C4—C5	108.21 (16)	C11—C12—C13	120.4 (2)
C3—C4—H4	125.9	C11—C12—H12	119.8
C5—C4—H4	125.9	C13—C12—H12	119.8
N1—C5—C4	106.34 (14)	C14—C13—C12	120.0 (2)
N1—C5—C6	122.59 (15)	C14—C13—H13	120.0
C4—C5—C6	131.06 (16)	C12—C13—H13	120.0
C7—C6—C5	126.73 (17)	C13—C14—C9	121.0 (2)
C7—C6—H6	116.6	C13—C14—H14	119.5
C5—C6—H6	116.6	C9—C14—H14	119.5
C6—C7—C8	121.53 (17)	C2—N1—C5	108.86 (15)
C6—C7—H7	119.2	C2—N1—C1	124.94 (16)
C8—C7—H7	119.2	C5—N1—C1	126.19 (14)
N1—C2—C3—C4	−0.4 (2)	C8—C9—C10—C11	177.39 (17)
C2—C3—C4—C5	−0.4 (2)	C9—C10—C11—C12	1.2 (3)
C3—C4—C5—N1	1.03 (18)	C10—C11—C12—C13	−1.1 (3)
C3—C4—C5—C6	−178.39 (17)	C11—C12—C13—C14	0.2 (3)
N1—C5—C6—C7	−175.01 (15)	C12—C13—C14—C9	0.6 (3)
C4—C5—C6—C7	4.3 (3)	C10—C9—C14—C13	−0.6 (3)
C5—C6—C7—C8	−178.64 (15)	C8—C9—C14—C13	−178.38 (16)
C6—C7—C8—O1	11.5 (3)	C3—C2—N1—C5	1.1 (2)
C6—C7—C8—C9	−169.16 (15)	C3—C2—N1—C1	−177.72 (16)
O1—C8—C9—C10	−163.32 (17)	C4—C5—N1—C2	−1.29 (18)
C7—C8—C9—C10	17.3 (2)	C6—C5—N1—C2	178.19 (15)
O1—C8—C9—C14	14.4 (2)	C4—C5—N1—C1	177.48 (15)
C7—C8—C9—C14	−164.97 (15)	C6—C5—N1—C1	−3.0 (2)
C14—C9—C10—C11	−0.3 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1C···O1i	0.96	2.49	3.434 (2)	169
C6—H6···O1	0.93	2.48	2.797 (2)	100

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1C⋯O1i	0.96	2.49	3.434 (2)	169

Symmetry code: (i) .