(2E)-3-(4-Chloro-phen-yl)-1-(1H-pyrrol-2-yl)prop-2-en-1-one.

In the mol-ecule of the title compound, C(13)H(10)ClNO, the benzene and pyrrole rings are oriented at a dihedral angle of 7.37 (12)°. In the crystal structure, inter-molecular N-H⋯O hydrogen bonds link the mol-ecules into centrosymmetric R(2) (2)(10) dimers. There are C-H⋯π inter-actions between benzene and pyrrole rings and a benzene C-H group. A weak π-π inter-action between the pyrrole rings [centroid-centroid distance 3.8515 (11) Å] further stabilizes the structure. There is also a π inter-action between the pyrrole ring and the carbonyl group, with a carbon-centroid distance of 3.4825 (18) Å.

Related literature

For general background, see: Varga et al. (2003 ▶); Katritzky & Rees (1984 ▶); Wu et al. (2003 ▶); Nam et al. (2003 ▶); Sondhi et al. (2005 ▶); Miyazaki et al. (2005 ▶). For related literature, see: Powers et al. (1998 ▶); Hu et al. (2006 ▶); Wang et al. (2005 ▶); Zeng & Cen (2006 ▶). For ring motif details, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C13H10ClNO

M = 231.67

Monoclinic,

a = 13.0401 (7) Å

b = 5.6326 (3) Å

c = 15.6857 (8) Å

β = 94.979 (3)°

V = 1147.76 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.31 mm−1

T = 296 (2) K

0.30 × 0.22 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.903, T max = 0.935

13745 measured reflections

3081 independent reflections

2180 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.128

S = 1.02

3081 reflections

185 parameters

All H-atom parameters refined

Δρmax = 0.29 e Å−3

Δρmin = −0.30 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: APEX2; 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: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2003 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808010362/hk2452sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808010362/hk2452Isup2.hkl

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

C13H10ClNO	F000 = 480
Mr = 231.67	Dx = 1.341 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2883 reflections
a = 13.0401 (7) Å	θ = 2.4–28.7º
b = 5.6326 (3) Å	µ = 0.31 mm−1
c = 15.6857 (8) Å	T = 296 (2) K
β = 94.979 (3)º	Prismatic, light yellow
V = 1147.76 (10) Å3	0.30 × 0.22 × 0.20 mm
Z = 4

Bruker KappaAPEXII CCD diffractometer	3081 independent reflections
Radiation source: fine-focus sealed tube	2180 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.026
Detector resolution: 7.30 pixels mm-1	θmax = 29.1º
T = 296(2) K	θmin = 1.6º
ω scans	h = −17→17
Absorption correction: multi-scan(SADABS; Bruker, 2005)	k = −7→7
Tmin = 0.903, Tmax = 0.935	l = −21→21
13745 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.043	All H-atom parameters refined
wR(F2) = 0.128	w = 1/[σ2(Fo2) + (0.0533P)2 + 0.3294P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max < 0.001
3081 reflections	Δρmax = 0.29 e Å−3
185 parameters	Δρmin = −0.30 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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 > 2sigma(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
Cl	0.47349 (5)	−0.30082 (12)	0.06812 (4)	0.0972 (3)
O1	0.10949 (10)	0.4232 (2)	0.43283 (8)	0.0672 (4)
N1	0.05564 (11)	0.2306 (3)	0.58749 (10)	0.0572 (4)
C1	0.29765 (11)	0.0517 (3)	0.26744 (10)	0.0464 (3)
C2	0.34920 (13)	−0.1623 (3)	0.28485 (11)	0.0525 (4)
C3	0.40411 (13)	−0.2692 (3)	0.22394 (12)	0.0566 (4)
C4	0.40726 (13)	−0.1631 (3)	0.14559 (11)	0.0563 (4)
C5	0.35867 (14)	0.0498 (3)	0.12645 (11)	0.0588 (4)
C6	0.30445 (13)	0.1551 (3)	0.18805 (11)	0.0537 (4)
C7	0.23600 (12)	0.1706 (3)	0.32855 (10)	0.0503 (4)
C8	0.20870 (13)	0.0873 (3)	0.40137 (11)	0.0548 (4)
C9	0.14204 (12)	0.2253 (3)	0.45499 (11)	0.0522 (4)
C10	0.11764 (11)	0.1179 (3)	0.53393 (10)	0.0501 (4)
C11	0.14707 (13)	−0.0945 (3)	0.57282 (11)	0.0566 (4)
C12	0.10275 (15)	−0.1076 (4)	0.65000 (13)	0.0659 (5)
C13	0.04627 (14)	0.0958 (4)	0.65667 (12)	0.0668 (5)
H2	0.3481 (14)	−0.236 (3)	0.3387 (13)	0.066 (5)*
H3	0.4387 (13)	−0.413 (3)	0.2358 (11)	0.062 (5)*
H6	0.2713 (14)	0.300 (4)	0.1763 (12)	0.063 (5)*
H5	0.3607 (15)	0.124 (4)	0.0702 (14)	0.075 (6)*
H7	0.2116 (14)	0.324 (4)	0.3102 (12)	0.067 (5)*
H8	0.2289 (15)	−0.069 (4)	0.4203 (13)	0.076 (6)*
H1	0.0220 (17)	0.353 (4)	0.5749 (14)	0.073 (6)*
H11	0.1896 (14)	−0.211 (3)	0.5521 (12)	0.063 (5)*
H12	0.1118 (15)	−0.226 (4)	0.6931 (14)	0.075 (6)*
H13	0.0089 (17)	0.150 (4)	0.7011 (15)	0.091 (7)*

	U11	U22	U33	U12	U13	U23
Cl	0.1189 (5)	0.0979 (5)	0.0810 (4)	0.0298 (3)	0.0442 (3)	−0.0182 (3)
O1	0.0738 (8)	0.0584 (7)	0.0716 (8)	0.0223 (6)	0.0185 (6)	−0.0044 (6)
N1	0.0521 (7)	0.0644 (9)	0.0560 (8)	0.0095 (7)	0.0107 (6)	−0.0144 (7)
C1	0.0443 (7)	0.0442 (7)	0.0509 (8)	0.0037 (6)	0.0063 (6)	−0.0076 (6)
C2	0.0576 (9)	0.0474 (8)	0.0535 (9)	0.0092 (7)	0.0107 (7)	0.0012 (7)
C3	0.0576 (9)	0.0457 (8)	0.0676 (11)	0.0115 (7)	0.0123 (8)	−0.0056 (7)
C4	0.0568 (9)	0.0561 (9)	0.0578 (9)	0.0044 (7)	0.0144 (7)	−0.0152 (7)
C5	0.0653 (10)	0.0612 (10)	0.0512 (9)	0.0050 (8)	0.0120 (7)	−0.0006 (8)
C6	0.0584 (9)	0.0467 (8)	0.0567 (9)	0.0107 (7)	0.0083 (7)	0.0008 (7)
C7	0.0500 (8)	0.0475 (8)	0.0536 (9)	0.0098 (6)	0.0062 (6)	−0.0073 (7)
C8	0.0558 (9)	0.0531 (9)	0.0565 (9)	0.0132 (7)	0.0113 (7)	−0.0078 (7)
C9	0.0481 (8)	0.0550 (9)	0.0537 (9)	0.0078 (7)	0.0062 (6)	−0.0136 (7)
C10	0.0439 (7)	0.0546 (9)	0.0518 (8)	0.0040 (6)	0.0048 (6)	−0.0162 (7)
C11	0.0531 (9)	0.0556 (9)	0.0614 (10)	0.0012 (7)	0.0072 (7)	−0.0107 (8)
C12	0.0647 (10)	0.0701 (12)	0.0638 (11)	−0.0064 (9)	0.0113 (8)	−0.0008 (10)
C13	0.0576 (10)	0.0844 (13)	0.0604 (11)	−0.0042 (9)	0.0163 (8)	−0.0137 (10)

Cl—C4	1.7339 (15)	C5—H5	0.98 (2)
O1—C9	1.232 (2)	C6—H6	0.94 (2)
N1—C13	1.338 (3)	C7—C8	1.312 (2)
N1—C10	1.3711 (19)	C7—H7	0.96 (2)
N1—H1	0.83 (2)	C8—C9	1.481 (2)
C1—C6	1.384 (2)	C8—H8	0.96 (2)
C1—C2	1.396 (2)	C9—C10	1.438 (2)
C1—C7	1.465 (2)	C10—C11	1.382 (2)
C2—C3	1.381 (2)	C11—C12	1.388 (3)
C2—H2	0.94 (2)	C11—H11	0.937 (19)
C3—C4	1.370 (3)	C12—C13	1.371 (3)
C3—H3	0.938 (18)	C12—H12	0.95 (2)
C4—C5	1.377 (2)	C13—H13	0.94 (2)
C5—C6	1.380 (2)
C13—N1—C10	109.55 (16)	C8—C7—C1	127.72 (15)
C13—N1—H1	125.3 (15)	C8—C7—H7	118.5 (12)
C10—N1—H1	124.5 (15)	C1—C7—H7	113.7 (12)
C6—C1—C2	118.16 (14)	C7—C8—C9	121.58 (16)
C6—C1—C7	118.54 (14)	C7—C8—H8	120.7 (12)
C2—C1—C7	123.29 (15)	C9—C8—H8	117.7 (12)
C3—C2—C1	120.73 (16)	O1—C9—C10	121.80 (14)
C3—C2—H2	118.7 (12)	O1—C9—C8	121.29 (16)
C1—C2—H2	120.6 (12)	C10—C9—C8	116.91 (14)
C4—C3—C2	119.22 (16)	N1—C10—C11	106.62 (15)
C4—C3—H3	120.2 (11)	N1—C10—C9	121.27 (15)
C2—C3—H3	120.5 (11)	C11—C10—C9	132.10 (14)
C3—C4—C5	121.75 (15)	C10—C11—C12	108.08 (16)
C3—C4—Cl	119.27 (13)	C10—C11—H11	127.2 (12)
C5—C4—Cl	118.98 (14)	C12—C11—H11	124.7 (12)
C4—C5—C6	118.40 (16)	C13—C12—C11	106.80 (18)
C4—C5—H5	121.3 (12)	C13—C12—H12	124.5 (13)
C6—C5—H5	120.3 (12)	C11—C12—H12	128.6 (13)
C5—C6—C1	121.72 (15)	N1—C13—C12	108.94 (17)
C5—C6—H6	119.6 (12)	N1—C13—H13	120.7 (15)
C1—C6—H6	118.7 (12)	C12—C13—H13	130.3 (15)
C6—C1—C2—C3	−0.9 (2)	C7—C8—C9—O1	0.3 (3)
C7—C1—C2—C3	178.38 (16)	C7—C8—C9—C10	−179.47 (15)
C1—C2—C3—C4	−0.3 (3)	C13—N1—C10—C11	−0.09 (19)
C2—C3—C4—C5	1.2 (3)	C13—N1—C10—C9	−179.06 (15)
C2—C3—C4—Cl	−178.39 (13)	O1—C9—C10—N1	0.9 (2)
C3—C4—C5—C6	−1.0 (3)	C8—C9—C10—N1	−179.32 (14)
Cl—C4—C5—C6	178.67 (14)	O1—C9—C10—C11	−177.75 (17)
C4—C5—C6—C1	−0.3 (3)	C8—C9—C10—C11	2.0 (3)
C2—C1—C6—C5	1.2 (3)	N1—C10—C11—C12	−0.27 (19)
C7—C1—C6—C5	−178.12 (15)	C9—C10—C11—C12	178.54 (17)
C6—C1—C7—C8	170.00 (17)	C10—C11—C12—C13	0.5 (2)
C2—C1—C7—C8	−9.3 (3)	C10—N1—C13—C12	0.4 (2)
C1—C7—C8—C9	−177.33 (15)	C11—C12—C13—N1	−0.6 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.83 (2)	2.12 (2)	2.902 (2)	156 (2)
C3—H3···CgAii	0.938 (18)	2.897 (17)	3.6339 (19)	136.4 (13)
C6—H6···CgBiii	0.94 (2)	2.651 (19)	3.4017 (19)	137.8 (16)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.83 (2)	2.12 (2)	2.902 (2)	156 (2)
C3—H3⋯CgAii	0.938 (18)	2.897 (17)	3.6339 (19)	136.4 (13)
C6—H6⋯CgBiii	0.94 (2)	2.651 (19)	3.4017 (19)	137.8 (16)

Symmetry codes: (i) ; (ii) ; (iii) . CgA and CgB are the centroids of the C1–C6 and N1/C10–C13 rings, respectively.