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Crystal structure of 2-(4-chloro-phen-yl)-2-oxoethyl 3-bromo-benzoate.

Khan I, Ibrar A, Hameed S, White JM, Simpson J - Acta Crystallogr Sect E Struct Rep Online (2014)

Bottom Line: Three of these are generated by two C-H⋯O inter-actions and a C-H⋯Br contact, and form chains along c and along the ab cell diagonal.In addition, two inversion-related π-π stacking inter-actions between like aryl rings again form chains of mol-ecules but in this instance along the bc diagonal.These contacts generate infinite layers of mol-ecules parallel to (011) and stack the mol-ecules along the a-axis direction.

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Affiliation: Department of Chemistry, Quaid-i-Azam University, Islamabad 45320, Pakistan ; School of Chemistry, University of Nottingham, University Park, Nottingham NG7 2RD, England.

ABSTRACT
2-(4-Chloro-phen-yl)-2-oxoethyl 3-bromo-benzoate, C15H10BrClO3, was synthesized in a single-step reaction by condensation of 3-bromo-benzoic acid with 2-bromo-1-(4-chloro-phen-yl)ethanone in di-methyl-formamide in the presence of tri-ethyl-amine as a catalyst. The structure consists of an aryl ketone moiety linked to an aryl ester unit by a methyl-ene group. Both units are reasonably planar (r.m.s. deviations of 0.119 and 0.010 Å for the aryl ketone and aryl ester units, respectively) and are almost orthogonal, with an angle of 88.60 (3)° between them. In the crystal, mol-ecules form five separate sets of inversion dimers. Three of these are generated by two C-H⋯O inter-actions and a C-H⋯Br contact, and form chains along c and along the ab cell diagonal. In addition, two inversion-related π-π stacking inter-actions between like aryl rings again form chains of mol-ecules but in this instance along the bc diagonal. These contacts generate infinite layers of mol-ecules parallel to (011) and stack the mol-ecules along the a-axis direction.

No MeSH data available.


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Chains of linked inversion dimers generated by C—H⋯O and C—H⋯Br hydrogen bonds, drawn as dashed lines.
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fig2: Chains of linked inversion dimers generated by C—H⋯O and C—H⋯Br hydrogen bonds, drawn as dashed lines.

Mentions: In the crystal structure, each mol­ecule forms five separate inversion dimers. C8—H8B⋯O1 and C15—H15 O3 hydrogen bonds each generate (10) rings, forming zigzag chains along c. Additional C4—H4⋯Br1 contacts also form inversion dimers with (8) rings and these combine with the C8—H8B⋯O1 contacts to link alternating pairs of dimers into infinite chains approximately along the ab cell diagonal, Table 1 ▶, Fig. 2 ▶. Inter­estingly, infinite chains of alternating inversion dimers also result from a pair of π–π stacking inter­actions between adjacent 3-bromo­phenyl rings, Cg1⋯Cg1iv = 3.6987 (10) Å, and neighbouring 4-chloro­phenyl rings Cg2⋯Cg2v = 3.8585 (11) Å, in this case along the bc diagonal, Fig. 3 ▶ [Cg1 and Cg2 are the centroids of the C1–C6 and C10–C15 rings, respectively; symmetry codes (iv) −x, 2 − y, −z; (v) 2 − x, 1 − y, 1 − z]. These contacts combine to generate extended layers of mol­ecules parallel to (011), Fig. 4 ▶, and to stack mol­ecules along the a-axis direction, Fig. 5 ▶.


Crystal structure of 2-(4-chloro-phen-yl)-2-oxoethyl 3-bromo-benzoate.

Khan I, Ibrar A, Hameed S, White JM, Simpson J - Acta Crystallogr Sect E Struct Rep Online (2014)

Chains of linked inversion dimers generated by C—H⋯O and C—H⋯Br hydrogen bonds, drawn as dashed lines.
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4257351&req=5

fig2: Chains of linked inversion dimers generated by C—H⋯O and C—H⋯Br hydrogen bonds, drawn as dashed lines.
Mentions: In the crystal structure, each mol­ecule forms five separate inversion dimers. C8—H8B⋯O1 and C15—H15 O3 hydrogen bonds each generate (10) rings, forming zigzag chains along c. Additional C4—H4⋯Br1 contacts also form inversion dimers with (8) rings and these combine with the C8—H8B⋯O1 contacts to link alternating pairs of dimers into infinite chains approximately along the ab cell diagonal, Table 1 ▶, Fig. 2 ▶. Inter­estingly, infinite chains of alternating inversion dimers also result from a pair of π–π stacking inter­actions between adjacent 3-bromo­phenyl rings, Cg1⋯Cg1iv = 3.6987 (10) Å, and neighbouring 4-chloro­phenyl rings Cg2⋯Cg2v = 3.8585 (11) Å, in this case along the bc diagonal, Fig. 3 ▶ [Cg1 and Cg2 are the centroids of the C1–C6 and C10–C15 rings, respectively; symmetry codes (iv) −x, 2 − y, −z; (v) 2 − x, 1 − y, 1 − z]. These contacts combine to generate extended layers of mol­ecules parallel to (011), Fig. 4 ▶, and to stack mol­ecules along the a-axis direction, Fig. 5 ▶.

Bottom Line: Three of these are generated by two C-H⋯O inter-actions and a C-H⋯Br contact, and form chains along c and along the ab cell diagonal.In addition, two inversion-related π-π stacking inter-actions between like aryl rings again form chains of mol-ecules but in this instance along the bc diagonal.These contacts generate infinite layers of mol-ecules parallel to (011) and stack the mol-ecules along the a-axis direction.

View Article: PubMed Central - HTML - PubMed

Affiliation: Department of Chemistry, Quaid-i-Azam University, Islamabad 45320, Pakistan ; School of Chemistry, University of Nottingham, University Park, Nottingham NG7 2RD, England.

ABSTRACT
2-(4-Chloro-phen-yl)-2-oxoethyl 3-bromo-benzoate, C15H10BrClO3, was synthesized in a single-step reaction by condensation of 3-bromo-benzoic acid with 2-bromo-1-(4-chloro-phen-yl)ethanone in di-methyl-formamide in the presence of tri-ethyl-amine as a catalyst. The structure consists of an aryl ketone moiety linked to an aryl ester unit by a methyl-ene group. Both units are reasonably planar (r.m.s. deviations of 0.119 and 0.010 Å for the aryl ketone and aryl ester units, respectively) and are almost orthogonal, with an angle of 88.60 (3)° between them. In the crystal, mol-ecules form five separate sets of inversion dimers. Three of these are generated by two C-H⋯O inter-actions and a C-H⋯Br contact, and form chains along c and along the ab cell diagonal. In addition, two inversion-related π-π stacking inter-actions between like aryl rings again form chains of mol-ecules but in this instance along the bc diagonal. These contacts generate infinite layers of mol-ecules parallel to (011) and stack the mol-ecules along the a-axis direction.

No MeSH data available.


Related in: MedlinePlus