4-(2-Chloro-phenyl-amino)-pent-3-en-2-one.

In the title compound, C(11)H(12)ClNO, intra-molecular N-H⋯O hydrogen bonding is present. The dihedral angle between the benzene ring and the pentenone unit is 46.52 (5)°. In the crystal, C-H⋯O inter-actions between hydrogen atoms of the aryl moiety and two separate oxygen atoms occur, leading to a three-dimensional network.

Related literature

For synthetic background and similar compounds, see: Shaheen et al. (2006 ▶); Venter et al. (2010 ▶, 2012b ▶). For applications, see: Brink et al. (2010 ▶); Pyżuk et al. (1993 ▶); Roodt & Steyn (2000 ▶); Tan et al. (2008 ▶); Xia et al. (2008 ▶). For related ligand systems, see: Damoense et al. (1994 ▶), Venter et al. (2012a ▶).

Experimental

Crystal data

C11H12ClNO

M = 209.67

Orthorhombic,

a = 7.3264 (3) Å

b = 8.7103 (4) Å

c = 16.1960 (7) Å

V = 1033.55 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.33 mm−1

T = 100 K

0.6 × 0.42 × 0.21 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.825, T max = 0.933

17399 measured reflections

2259 independent reflections

2211 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.025

wR(F 2) = 0.068

S = 1.06

2259 reflections

126 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.21 e Å−3

Δρmin = −0.24 e Å−3

Absolute structure: Flack (1983 ▶), 932 Friedel pairs

Flack parameter: 0.01 (5)

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT-Plus (Bruker, 2004 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg & Putz, 2005 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812042043/pk2444sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812042043/pk2444Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812042043/pk2444Isup3.cml

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

C11H12ClNO	F(000) = 440
Mr = 209.67	Dx = 1.347 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 5717 reflections
a = 7.3264 (3) Å	θ = 2.7–28.3°
b = 8.7103 (4) Å	µ = 0.33 mm−1
c = 16.1960 (7) Å	T = 100 K
V = 1033.55 (8) Å3	Cuboid, yellow
Z = 4	0.6 × 0.42 × 0.21 mm

Bruker APEXII CCD area-detector diffractometer	2259 independent reflections
Radiation source: fine-focus sealed tube	2211 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.032
φ and ω scans	θmax = 27.0°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −9→9
Tmin = 0.825, Tmax = 0.933	k = −11→11
17399 measured reflections	l = −20→19

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)] = 0.025	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.068	w = 1/[σ2(Fo2) + (0.0376P)2 + 0.2837P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max = 0.013
2259 reflections	Δρmax = 0.21 e Å−3
126 parameters	Δρmin = −0.24 e Å−3
0 restraints	Absolute structure: Flack (1983), 932 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.01 (5)

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
Cl12	0.00235 (5)	0.20519 (4)	0.531562 (19)	0.02339 (10)
N11	0.21805 (15)	0.28866 (14)	0.67897 (7)	0.0174 (2)
H11	0.2500 (8)	0.209 (2)	0.6556 (6)	0.027 (5)*
O12	0.33003 (14)	0.00171 (12)	0.68371 (6)	0.02136 (18)
C3	0.24678 (18)	0.14426 (16)	0.80149 (9)	0.0178 (3)
H3	0.2362	0.1411	0.8599	0.021*
C2	0.20915 (17)	0.28095 (16)	0.76209 (8)	0.0169 (3)
C111	0.18055 (18)	0.41335 (16)	0.62662 (8)	0.0166 (3)
C116	0.2464 (2)	0.56091 (16)	0.64159 (9)	0.0197 (3)
H116	0.3191	0.5797	0.6891	0.024*
C4	0.3006 (2)	0.00740 (18)	0.75983 (9)	0.02136 (18)
C113	0.04201 (19)	0.50725 (19)	0.49974 (9)	0.0229 (3)
H113	−0.0264	0.4881	0.451	0.027*
C5	0.3168 (2)	−0.13853 (17)	0.80936 (9)	0.0227 (3)
H5A	0.2032	−0.1974	0.8047	0.034*
H5B	0.339	−0.1131	0.8674	0.034*
H5C	0.4185	−0.2	0.7881	0.034*
C112	0.08035 (18)	0.38927 (17)	0.55421 (9)	0.0184 (3)
C115	0.20717 (19)	0.68074 (17)	0.58791 (9)	0.0226 (3)
H115	0.2505	0.7812	0.5996	0.027*
C1	0.1554 (2)	0.41966 (16)	0.81135 (9)	0.0203 (3)
H1A	0.2628	0.4845	0.8205	0.03*
H1B	0.1056	0.3871	0.8647	0.03*
H1C	0.0627	0.478	0.7811	0.03*
C114	0.1048 (2)	0.65395 (18)	0.51727 (9)	0.0243 (3)
H114	0.0776	0.7363	0.4808	0.029*

	U11	U22	U33	U12	U13	U23
Cl12	0.02513 (17)	0.02720 (17)	0.01784 (17)	−0.00589 (15)	−0.00152 (14)	−0.00549 (12)
N11	0.0194 (5)	0.0181 (5)	0.0146 (5)	0.0016 (5)	−0.0004 (4)	−0.0024 (5)
O12	0.0232 (4)	0.0229 (4)	0.0180 (4)	−0.0007 (3)	0.0032 (3)	−0.0004 (3)
C3	0.0158 (6)	0.0234 (7)	0.0140 (7)	−0.0011 (5)	−0.0006 (5)	−0.0012 (5)
C2	0.0122 (6)	0.0218 (6)	0.0167 (6)	−0.0010 (5)	−0.0007 (5)	−0.0026 (5)
C111	0.0136 (6)	0.0216 (6)	0.0145 (6)	0.0013 (5)	0.0015 (5)	−0.0012 (5)
C116	0.0168 (6)	0.0224 (6)	0.0198 (7)	−0.0008 (5)	0.0010 (5)	−0.0028 (5)
C4	0.0232 (4)	0.0229 (4)	0.0180 (4)	−0.0007 (3)	0.0032 (3)	−0.0004 (3)
C113	0.0202 (7)	0.0333 (7)	0.0152 (6)	0.0025 (6)	0.0003 (5)	0.0019 (6)
C5	0.0211 (6)	0.0230 (7)	0.0241 (8)	0.0020 (6)	0.0011 (6)	0.0025 (6)
C112	0.0151 (6)	0.0236 (7)	0.0165 (7)	−0.0019 (5)	0.0026 (5)	−0.0027 (5)
C115	0.0212 (7)	0.0224 (7)	0.0242 (7)	−0.0013 (6)	0.0062 (5)	0.0008 (6)
C1	0.0212 (6)	0.0221 (7)	0.0175 (7)	0.0018 (5)	0.0007 (5)	−0.0032 (5)
C114	0.0228 (7)	0.0276 (7)	0.0224 (8)	0.0032 (6)	0.0042 (6)	0.0077 (6)

Cl12—C112	1.7412 (15)	C4—C5	1.508 (2)
N11—C2	1.3494 (18)	C113—C112	1.383 (2)
N11—C111	1.4049 (18)	C113—C114	1.387 (2)
N11—H11	0.8243	C113—H113	0.95
O12—C4	1.2524 (18)	C5—H5A	0.98
C3—C2	1.3787 (19)	C5—H5B	0.98
C3—C4	1.425 (2)	C5—H5C	0.98
C3—H3	0.95	C115—C114	1.388 (2)
C2—C1	1.5005 (19)	C115—H115	0.95
C111—C116	1.3942 (19)	C1—H1A	0.98
C111—C112	1.3994 (19)	C1—H1B	0.98
C116—C115	1.389 (2)	C1—H1C	0.98
C116—H116	0.95	C114—H114	0.95
C2—N11—C111	129.12 (13)	C4—C5—H5A	109.5
C2—N11—H11	115.4	C4—C5—H5B	109.5
C111—N11—H11	115.4	H5A—C5—H5B	109.5
C2—C3—C4	123.95 (13)	C4—C5—H5C	109.5
C2—C3—H3	118	H5A—C5—H5C	109.5
C4—C3—H3	118	H5B—C5—H5C	109.5
N11—C2—C3	119.67 (12)	C113—C112—C111	121.98 (13)
N11—C2—C1	120.21 (13)	C113—C112—Cl12	118.89 (11)
C3—C2—C1	120.11 (12)	C111—C112—Cl12	119.13 (11)
C116—C111—C112	117.74 (13)	C114—C115—C116	120.12 (13)
C116—C111—N11	122.69 (12)	C114—C115—H115	119.9
C112—C111—N11	119.50 (12)	C116—C115—H115	119.9
C115—C116—C111	120.82 (13)	C2—C1—H1A	109.5
C115—C116—H116	119.6	C2—C1—H1B	109.5
C111—C116—H116	119.6	H1A—C1—H1B	109.5
O12—C4—C3	123.13 (14)	C2—C1—H1C	109.5
O12—C4—C5	118.48 (14)	H1A—C1—H1C	109.5
C3—C4—C5	118.35 (13)	H1B—C1—H1C	109.5
C112—C113—C114	119.11 (14)	C113—C114—C115	120.18 (14)
C112—C113—H113	120.4	C113—C114—H114	119.9
C114—C113—H113	120.4	C115—C114—H114	119.9
C111—N11—C2—C3	177.99 (12)	C114—C113—C112—C111	0.1 (2)
C111—N11—C2—C1	−0.9 (2)	C114—C113—C112—Cl12	−179.63 (11)
C4—C3—C2—N11	1.8 (2)	C116—C111—C112—C113	−1.8 (2)
C4—C3—C2—C1	−179.31 (13)	N11—C111—C112—C113	−178.91 (12)
C2—N11—C111—C116	46.2 (2)	C116—C111—C112—Cl12	177.84 (10)
C2—N11—C111—C112	−136.84 (15)	N11—C111—C112—Cl12	0.77 (17)
C112—C111—C116—C115	2.6 (2)	C111—C116—C115—C114	−1.5 (2)
N11—C111—C116—C115	179.53 (13)	C112—C113—C114—C115	1.1 (2)
C2—C3—C4—O12	4.7 (2)	C116—C115—C114—C113	−0.3 (2)
C2—C3—C4—C5	−173.14 (12)

D—H···A	D—H	H···A	D···A	D—H···A
N11—H11···O12	0.82	1.95	2.6317 (16)	139
C113—H113···O12i	0.95	2.42	3.3536 (18)	166
C115—H115···O12ii	0.95	2.43	3.3217 (18)	157

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N11—H11⋯O12	0.82	1.95	2.6317 (16)	139
C113—H113⋯O12i	0.95	2.42	3.3536 (18)	166
C115—H115⋯O12ii	0.95	2.43	3.3217 (18)	157

Symmetry codes: (i) ; (ii) .