3-(4-Bromo­anilino)-3-(4-chloro­phen­yl)-1-phenyl­propan-1-one

Mehrdad Pourayoubi; Zohreh Shobeiri; Giuseppe Bruno; Hadi Amiri Rudbari

doi:10.1107/S1600536811036932

. 2011 Sep 17;67(Pt 10):o2647. doi: 10.1107/S1600536811036932

3-(4-Bromoanilino)-3-(4-chlorophenyl)-1-phenylpropan-1-one

Mehrdad Pourayoubi ^a,^*, Zohreh Shobeiri ^a, Giuseppe Bruno ^b, Hadi Amiri Rudbari ^b

PMCID: PMC3201452 PMID: 22064785

Abstract

The asymmetric C atom in the title compound, C₂₁H₁₇BrClNO, is in a slightly distorted tetrahedral environment and the NH unit adopts a gauche orientation with respect to the CO group. In the crystal, pairs of intermolecular N—H⋯O hydrogen bonds form centrosymmetric dimers.

Related literature

For background to β-amino ketones, see: Scettri et al. (2008 ▶). For related structures, see: Shobeiri et al. (2011 ▶); Zhang et al. (2008 ▶). For hydrogen-bond motifs and their graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C₂₁H₁₇BrClNO
M _r = 414.72
Monoclinic,
a = 10.6571 (4) Å
b = 17.2432 (6) Å
c = 10.8602 (4) Å
β = 113.571 (2)°
V = 1829.19 (12) Å³
Z = 4
Mo Kα radiation
μ = 2.40 mm⁻¹
T = 296 K
0.35 × 0.31 × 0.11 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T _min = 0.589, T _max = 0.746
69312 measured reflections
3983 independent reflections
3274 reflections with I > 2σ(I)
R _int = 0.036

Refinement

R[F ² > 2σ(F ²)] = 0.033
wR(F ²) = 0.084
S = 1.03
3983 reflections
230 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.71 e Å⁻³
Δρ_min = −0.86 e Å⁻³

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); 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 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811036932/qm2027sup1.cif

e-67-o2647-sup1.cif^{(23.1KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811036932/qm2027Isup2.hkl

e-67-o2647-Isup2.hkl^{(191.3KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811036932/qm2027Isup3.cml

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—H⋯O1ⁱ	0.81 (3)	2.23 (3)	2.992 (3)	156 (2)

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Symmetry code: (i) Inline graphic .

Acknowledgments

Support of this investigation by Ferdowsi University of Mashhad is gratefully acknowledged.

supplementary crystallographic information

Comment

β-Amino ketones, of the formula [R¹]CH[NHR²][CH₂C(O)R³], such as the title compound have attracted attention because of their roles as important intermediates for the synthesis of natural products and chiral auxiliaries (Scettri et al., 2008). In the previous work, the structure determination of 3-(4-bromophenylamino)-1-phenyl-3-p-tolylpropan-1-one (Shobeiri et al., 2011) has been investigated. Here, we report the synthesis and crystal structure of the title molecule, [4-Cl—C₆H₄]CH[NHC₆H₄-4-Br][CH₂C(O)C₆H₅]. The asymmetric C atom has a slightly distorted tetrahedral configuration (Fig 1) with the bond angles in the range of 107.92 (16)° [N(1)—C(9)—C(8)] to 114.69 (16)° [N(1)—C(9)—C(10)]. In the crystal, pairs of intermolecular N—H···O(C) hydrogen bonds (Table 1) form centrosymmetric dimers as R₂²(12) rings (for graph-set notation, see Bernstein et al., 1995). A view of crystal packing is shown in Fig. 2.

Experimental

To a magnetically stirred mixture of 3-(4-chlorophenyl)-1-phenylprop-2-en-1-one (0.24 g, 1.0 mmol) and Ag₃PW₁₂O₄₀ (0.32 g, 0.10 mmol) as catalyst, in ethanol (5 ml), 4-bromoaniline (0.20 g, 1.2 mmol) was added at room temperature. The reaction completion was monitored by thin layer chromatography (TLC). The catalyst Ag₃PW₁₂O₄₀ was collected by centrifugation. The reaction mixture was extracted with distilled water and ether (2×10 ml). The combined organic layer was evaporated to obtain crude product which was washed with hexane to give pure product. Single crystals of the product were obtained from a solution of CHCl₃/CH₃OH at room temperature.