(Z)-3-Chloro-3-phenyl-N-[(S)-1-phenyl­ethyl]prop-2-enamide

Neudo A Urdaneta; Teresa González; Alexander Briceño

doi:10.1107/S160053680801876X

. 2008 Jul 5;64(Pt 8):o1372. doi: 10.1107/S160053680801876X

(Z)-3-Chloro-3-phenyl-N-[(S)-1-phenylethyl]prop-2-enamide

Neudo A Urdaneta ^a,^*, Teresa González ^b, Alexander Briceño ^b,^*

PMCID: PMC2962220 PMID: 21203094

Abstract

The asymmetric unit of the title compound, C₁₇H₁₆ClNO, contains two crystallographically independent molecules. These molecules are connected in an alternating fashion through N—H⋯O and C—H⋯O hydrogen bonds, generating one-dimensional chains of graph sets R ₂ ¹(6) and C(4) along the a axis.

Related literature

For related literature, see: Kishikawa et al., (1997 ▶); Cherry et al. (2003 ▶); Pontiki & Hadjipavlou (2007 ▶); Urdaneta et al. (2004 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C₁₇H₁₆ClNO
M _r = 285.76
Orthorhombic,
a = 9.803 (3) Å
b = 14.976 (5) Å
c = 20.823 (6) Å
V = 3057.2 (15) Å³
Z = 8
Mo Kα radiation
μ = 0.24 mm⁻¹
T = 293 (2) K
0.48 × 0.38 × 0.28 mm

Data collection

Rigaku AFC-7S Mercury diffractometer
Absorption correction: multi-scan (Jacobson, 1998 ▶) T _min = 0.897, T _max = 0.985 (expected range = 0.850–0.934)
32660 measured reflections
5802 independent reflections
3687 reflections with I > 2σ(I)
R _int = 0.063

Refinement

R[F ² > 2σ(F ²)] = 0.070
wR(F ²) = 0.161
S = 1.07
5802 reflections
362 parameters
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.28 e Å⁻³
Absolute structure: Flack (1983 ▶), 1693 Friedel pairs
Flack parameter: −0.03 (9)

Data collection: CrystalClear (Rigaku, 2002 ▶); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku/MSC, 2004 ▶); program(s) used to solve structure: SHELXTL-NT (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL-NT; molecular graphics: SHELXTL-NT and DIAMOND (Brandenburg, 1999 ▶); software used to prepare material for publication: SHELXTL-NT and PLATON (Spek, 2003 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680801876X/hb2746sup1.cif

e-64-o1372-sup1.cif^{(23.1KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S160053680801876X/hb2746Isup2.hkl

e-64-o1372-Isup2.hkl^{(284.1KB, hkl)}

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2ⁱ	0.97	1.89	2.852 (4)	174
N2—H2N⋯O1	0.95	2.04	2.933 (5)	157
C10—H10⋯Cl1	0.93	2.64	3.021 (6)	105
C13—H13⋯N1	0.93	2.55	2.874 (5)	101
C19—H19⋯O1	0.93	2.50	3.315 (5)	146
C27—H27⋯Cl2	0.93	2.65	3.028 (6)	105
C30—H30⋯N2	0.93	2.65	2.951 (5)	99

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors thank FONACIT-MCT Venezuela for financial support (projects: LAB-199700821).

supplementary crystallographic information

Comment

The title compound, (I), represents a valuable intermediate for the synthesis of biologically active disubstituted pyrimidones (Cherry et al., 2003), phenyl-substituted amides with antioxidant and anti-inflamatory activity as novel lipoxygenase inhibitor (Pontiki & Hadjipavlou, 2007), and also as precursor for photochemical studies (Kishikawa et al., 1997).

The asymmetric unit of (I) contains two crystallographically indepedent molecules of the same stereochemical configuration (Fig. 1): C4 and C21 have S configuration. Each molecule displays two kinds of intramolecular C—H···Cl and C—H···N hydrogen bonds (Table 1). These interactions lead to the formation of five-membered rings described by graph-set symbol S(5) (Bernstein et al., 1995). In each molecule the phenyl groups are twisted with respect to the aliphatic chain defined by C4/N1/C3/O1/C2/C1 (CH1) and C21/N2/C18/C19/C20/O2 atoms (CH2), respectively. The dihedral angles between the C5—C10 and C12—C17 rings and the mean plane of the CH1 are 31.8 (2)° and 88.6 (2)°, for the molecule 1; C29—C34: 81.8 (2)° and C22—C2: 33.8 (2)° for the rings of the molecule 2. These molecules form a dimer linked through a N—H···O and C—H···O intermolecular hydrogen bonds in which the O atom from carbonyl group acts as a double aceptor of hydrogen bonds (Fig 1). This interaction produces a supramolecular motif described by the symbol R₂¹(6). These dimers are connected in an alternate fashion via remaining N—H···O intermolecular hydrogen bonds, generating one-dimensional chains along the a axis (Fig. 2), this interaction is described by the symbol C(4). Adjacent chains are assembled through C—H···π interactions to afford a three-dimensional array.

Experimental

The title compound was prepared according to a reported procedure (Urdaneta et al., 2004), and colourless blocks of (I) were grown from a saturated AcOEt/Et₂O (1:9) solution kept at 277 K.