3-(4-Bromo­phen­yl)cyclo­pent-2-en-1-one

Shurdha, E.; Dees, K.; Miller, H.A.; Iacono, S.T.; Balaich, G.J.

doi:10.1107/S160053681401071X

organic compounds

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ISSN: 2056-9890

Volume 70| Part 6| June 2014| Pages o692-o693

doi:10.1107/S160053681401071X

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3-(4-Bromophenyl)cyclopent-2-en-1-one

Endrit Shurdha,^a Kelsey Dees,^a Hannah A. Miller,^a Scott T. Iacono ^a and Gary J. Balaich ^a ^*

^aDepartment of Chemistry and Chemistry Research Center, 2355 Fairchild Drive, Suite 2N 225, United States Air Force Academy, Colorado Springs, CO 80840, USA
^*Correspondence e-mail: gary.balaich@usafa.edu

Edited by J. T. Mague, Tulane University, USA (Received 25 April 2014; accepted 9 May 2014; online 21 May 2014)

In the title compound, C₁₁H₉BrO, the cyclopentenone ring is almost planar with an r.m.s. deviation of 0.0097 Å. The largest inter-ring torsion angles [2.4 (3), 1.3 (3) and 3.53 (2)°] reveal only a very small twist between the rings, and suggest that the two rings are conjugated. The molecule is slightly bowed, as shown by the small dihedral angle between the rings [5.3 (1)°]. The crystal packing pattern consists of parallel sheets that stack parallel to the ac plane. Each sheet consists of molecules that pack side-to-side with the same relative orientation of phenyl and cyclopentenone rings along the a- and c-axis directions. Slipped side-to-side, face-to-face and edge-to-face interactions exist between pairs of sheets with edge-to-edge and edge-to-face O⋯H—C(sp²) weak hydrogen-bond contacts. A relatively short edge-to-face contact (2.77 Å) also exists between pairs of sheets.

CCDC reference: 999140

Related literature

For structures of related 3-Ph substituted cyclopent-2-ene-1-ones, see: Zhao et al. (2008 ); Marjani et al. (2007 , 2008 ); Jedrzejas et al. (1996 ). For leading references on the synthesis and uses of substituted cyclopentenones, see: Gibson et al. (2004 ); Gibson & Mainolfi (2005 ); Liu et al. (2013 ); Barluenga et al. (2012 ); Varea et al. (2012 ). For materials chemistry applications, see: Peloquin et al. (2012 ); Li et al. (2008 ). For the synthesis of the title compound, see: Heck (1965 ). For weak hydrogen bonds, see: Arunan et al. (2011 ).

Experimental

Crystal data

C₁₁H₉BrO
M_r = 237.09
Monoclinic, P 2₁ /c
a = 10.0219 (12) Å
b = 9.7818 (11) Å
c = 9.9945 (12) Å
β = 107.4375 (14)°
V = 934.76 (19) Å³
Z = 4
Mo Kα radiation
μ = 4.35 mm⁻¹
T = 100 K
0.30 × 0.13 × 0.07 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan SADABS (Bruker, 2013 ) T_min = 0.53, T_max = 0.75
9994 measured reflections
2316 independent reflections
1917 reflections with I > 2σ(I)
R_int = 0.031

Refinement

R[F² > 2σ(F²)] = 0.025
wR(F²) = 0.057
S = 1.02
2316 reflections
118 parameters
H-atom parameters constrained
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.46 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O1ⁱ	0.95	2.58	3.465 (2)	154
C7—H7⋯O1ⁱ	0.95	2.58	3.484 (3)	158
C10—H10⋯O1ⁱⁱ	0.95	2.52	3.377 (2)	150
Symmetry codes: (i) -x+1, -y, -z+1; (ii) $[x-1, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2013); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT; program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: SHELXP (Sheldrick, 2008) and Mercury (Macrae et al., 2008 ); software used to prepare material for publication: SHELXL2013 (Sheldrick, 2008).

Supporting information

CCDC reference: 999140

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681401071X/mw2122sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681401071X/mw2122Isup2.hkl

Supporting information file. DOI: 10.1107/S160053681401071X/mw2122Isup3.cdx

Supporting information file. DOI: 10.1107/S160053681401071X/mw2122Isup4.cml

checkCIF report

Comment top

Substituted cyclopentenones are found most frequently as intermediates for or parts of complex bioactive molecules and are synthesized by a variety of metal- and non-metal-mediated methodologies (Liu et al. (2013), Barluenga et al. (2012), Varea et al. (2012), Gibson et al. (2005), Gibson et al. (2004)). We are interested in the use of substituted cyclopentenones as intermediates in the synthesis of fulvenes or fulvene-based polymers with optoelectronic properties suitable for possible molecular electronics applications (Peloquin et al. (2012)). The title compound was targeted due to the importance of the Br substituent in Sonagashira or Suzuki coupling methods which will be used to extend the π conjugation of the cyclopentenone and resulting fulvene molecular frameworks. In the course of purifying the title compound, crystals were obtained and, as its structure had not been published, its structure was determined.

The title compound (Fig. 1) consists of a planar Ph ring and an almost planar cyclopentenone ring with r.m.s deviations from the least squares planes of 0.0062 Å (Ph) and 0.0097 Å (cyclopentenone). Conjugation of both rings is evident from the small torsion angles about the C3—C6 bond (C2C3C6C7 = 2.4 (3)°, C4C3C6C11 = 1.3 (3)° and C4C3C6C7 = 3.53 (2)°). The dihedral angle between the phenyl and cyclopentenone rings is 5.3 (1)° resulting in the molecule being slightly bowed along its long axis.

The crystal packing pattern consists of parallel sheets of cyclopentenone molecules (sheets A—D, Fig. 2) that stack parallel to the ac plane. Each sheet consists of molecules that pack side-to-side with the same relative orientation of Ph and cyclopentenone groups along the a- and c-axis directions. Slipped side-to-side, face-to-face and edge-to-face interactions exist between pairs of sheets AB, CD, BC, and AD. The shortest intermolecular contacts are weak O···H—C(sp²) hydrogen bonds (Table 1) with molecules in edge-to-edge and edge-to-face orientations. Although the D—H···A angles (Table 1) deviate substantially from the 180° expected for strong hydrogen bonds, they are large enough to be classified as weak hydrogen bonds (Arunan et al. (2011). Furthermore, the H···A distances are shorter than the sum of the H and O van der Waals radii (2.72 Å) (Arunan et al. (2011)). The shortest intermolecular contact besides the noted weak hydrogen bonds is the edge-to-face C11–H8 distance (2.77 Å).

Experimental top

The synthesis of the title compound was carried out using a modification to the original literature procedure (Heck (1965)). The diketone, 1-(4-bromophenyl)-1,4-pentanedione (10.0 g, 39.2 mmol) was combined with 0.5 M NaOH (1 L) and the reaction mixture vigorously stirred and heated at 90 °C for 4 hours. Aliquots were periodically removed to monitor the progress of the reaction by MS-TOF. The reaction mixture was allowed to cool and subsequently neutralized with 1M H₂SO₄. The resulting precipitate was collected by vacuum filtration, washed with water (100 mL), and vacuum dried to give a light brown crude product. Purification was best achieved by column chromatography (dry loaded from CH₂Cl₂) using an EtOAc/hexane mobile phase. A mobile phase of 10% EtOAc/hexane was used to initially remove the colored impurities. This process was followed by 20% EtOAc/hexane to obtain 3-(4-bromophenyl)cyclopent-2-en-1-one as a yellow solid (Yield 5.85 g, 63%). ¹H NMR (CDCl₃) d 2.55, 2.98 (m, 4H, CH₂); 6.52 (t, 1H, CHCO, ⁴J = 2 Hz); 7.48, 7.55 (m, 4H, BrPhH). ¹³C NMR (CDCl₃) d 28.5, 35.2 (CH₂); 125.6, 127.8, 128.1, 132.1, 132.9 (CH and C); 172.3 (CBr); 208.8 (CO). MS-TOF [M+H]⁺calcd. For C₁₁H₉BrO 236.9915; found 236.9927.

Refinement top

All hydrogen atoms were placed in calculated positions using a riding model (aryl C—H = 0.95 Å, methylene C—H = 0.99 Å; U_iso(H) = 1.2 U_eq(C)).

Related literature top

For structures of related 3-Ph substituted cyclopent-2-ene-1-ones, see: Zhao et al. (2008); Marjani et al. (2007, 2008); Jedrzejas et al. (1996). For leading references on the synthesis and uses of substituted cyclopentenones, see: Gibson et al. (2004); Gibson & Mainolfi (2005); Liu et al. (2013); Barluenga et al. (2012); Varea et al. (2012). For materials chemistry applications, see: Peloquin et al. (2012); Li et al. (2008). For the synthesis of the title compound, see: Heck (1965). For weak hydrogen bonds, see: Arunan et al. (2011).

Computing details top

Data collection: APEX2 (Bruker, 2013); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: SHELXS-2013 (Sheldrick, 2008); program(s) used to refine structure: SHELXL-2013 (Sheldrick, 2008); molecular graphics: SHELXP (Sheldrick, 2008) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of 3-(4-bromophenyl)cyclopent-2-en-1-one. Ellipsoids are shown at the 50% probability level.
	Fig. 2. Crystal packing view of 3-(4-bromophenyl)cyclopent-2-en-1-one. View is down the a axis, and shows sheets A-D which stack parallel to the ac plane. Ellipsoids are shown at the 50% probability level. Hydrogen atoms were omitted for clarity.
	Fig. 3. Molecular packing motifs depicting side-to-side and face-to-face intermolecular contacts. The bottom left diagram depicts the bowed molecular axis. The bottom right diagram indicates the C6–Ph ring centroid distance (3.43 Å), which is within error of the C7–C11 distances (3.42 Å, dashed lines). Ellipsoids are shown at the 50% probability level. Distances shown are in Å.

3-(4-Bromophenyl)cyclopent-2-en-1-one top

Crystal data top

C₁₁H₉BrO	D_x = 1.685 Mg m⁻³
M_r = 237.09	Melting point: 127.0 K
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 10.0219 (12) Å	Cell parameters from 3089 reflections
b = 9.7818 (11) Å	θ = 3.0–28.6°
c = 9.9945 (12) Å	µ = 4.35 mm⁻¹
β = 107.4375 (14)°	T = 100 K
V = 934.76 (19) Å³	Rectangular prism, colourless
Z = 4	0.30 × 0.13 × 0.07 mm
F(000) = 472

Data collection top

Bruker SMART APEX CCD diffractometer	2316 independent reflections
Radiation source: fine focus sealed tube	1917 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.031
Detector resolution: 8.3333 pixels mm^-1	θ_max = 28.3°, θ_min = 2.1°
ω scans	h = −13→13
Absorption correction: multi-scan SADABS (Bruker, 2013)	k = −12→13
T_min = 0.53, T_max = 0.75	l = −13→13
9994 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.025	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.057	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0233P)² + 0.4987P] where P = (F_o² + 2F_c²)/3
2316 reflections	(Δ/σ)_max = 0.001
118 parameters	Δρ_max = 0.35 e Å⁻³
0 restraints	Δρ_min = −0.46 e Å⁻³

Crystal data top

C₁₁H₉BrO	V = 934.76 (19) Å³
M_r = 237.09	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.0219 (12) Å	µ = 4.35 mm⁻¹
b = 9.7818 (11) Å	T = 100 K
c = 9.9945 (12) Å	0.30 × 0.13 × 0.07 mm
β = 107.4375 (14)°

Data collection top

Bruker SMART APEX CCD diffractometer	2316 independent reflections
Absorption correction: multi-scan SADABS (Bruker, 2013)	1917 reflections with I > 2σ(I)
T_min = 0.53, T_max = 0.75	R_int = 0.031
9994 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.025	0 restraints
wR(F²) = 0.057	H-atom parameters constrained
S = 1.02	Δρ_max = 0.35 e Å⁻³
2316 reflections	Δρ_min = −0.46 e Å⁻³
118 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Br1	−0.30717 (2)	0.07926 (2)	0.08100 (2)	0.02888 (8)
O1	0.59890 (14)	0.08928 (13)	0.72449 (14)	0.0228 (3)
C1	0.4771 (2)	0.12867 (19)	0.68736 (19)	0.0181 (4)
C2	0.3642 (2)	0.07755 (19)	0.56825 (19)	0.0181 (4)
H2	0.3743	0.0067	0.507	0.022*
C3	0.2442 (2)	0.14462 (17)	0.55725 (18)	0.0154 (4)
C4	0.2622 (2)	0.24952 (19)	0.67199 (19)	0.0204 (4)
H4A	0.2025	0.2274	0.732	0.024*
H4B	0.2377	0.342	0.6319	0.024*
C5	0.4180 (2)	0.2416 (2)	0.7563 (2)	0.0229 (4)
H5A	0.4655	0.3295	0.7519	0.027*
H5B	0.4294	0.2194	0.8558	0.027*
C6	0.10968 (19)	0.12424 (18)	0.44782 (18)	0.0152 (4)
C7	0.0981 (2)	0.03111 (18)	0.33801 (19)	0.0177 (4)
H7	0.1767	−0.0228	0.3368	0.021*
C8	−0.0265 (2)	0.01702 (19)	0.23155 (19)	0.0198 (4)
H8	−0.0338	−0.0465	0.1578	0.024*
C9	−0.1403 (2)	0.09624 (19)	0.23345 (19)	0.0187 (4)
C10	−0.1341 (2)	0.18783 (19)	0.34090 (19)	0.0191 (4)
H10	−0.2135	0.2406	0.3416	0.023*
C11	−0.0086 (2)	0.20035 (18)	0.44772 (19)	0.0181 (4)
H11	−0.0029	0.2622	0.5225	0.022*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.02309 (12)	0.03472 (13)	0.02207 (11)	0.00371 (9)	−0.00349 (8)	−0.00033 (8)
O1	0.0171 (7)	0.0241 (7)	0.0251 (7)	0.0006 (5)	0.0031 (6)	−0.0043 (6)
C1	0.0187 (10)	0.0163 (8)	0.0192 (9)	−0.0016 (7)	0.0054 (8)	−0.0006 (7)
C2	0.0183 (10)	0.0187 (9)	0.0179 (9)	−0.0011 (7)	0.0063 (8)	−0.0043 (7)
C3	0.0189 (9)	0.0134 (8)	0.0157 (8)	−0.0017 (7)	0.0077 (7)	0.0018 (6)
C4	0.0223 (10)	0.0172 (9)	0.0218 (9)	0.0016 (7)	0.0068 (8)	−0.0031 (7)
C5	0.0239 (10)	0.0203 (9)	0.0226 (9)	0.0004 (8)	0.0039 (8)	−0.0071 (8)
C6	0.0168 (9)	0.0135 (8)	0.0159 (8)	−0.0017 (7)	0.0061 (7)	0.0033 (6)
C7	0.0169 (10)	0.0175 (8)	0.0202 (9)	0.0012 (7)	0.0078 (8)	0.0007 (7)
C8	0.0219 (10)	0.0197 (9)	0.0180 (9)	−0.0028 (7)	0.0063 (8)	−0.0013 (7)
C9	0.0167 (10)	0.0215 (9)	0.0161 (9)	−0.0004 (7)	0.0021 (7)	0.0053 (7)
C10	0.0181 (10)	0.0178 (9)	0.0222 (9)	0.0041 (7)	0.0073 (8)	0.0028 (7)
C11	0.0211 (10)	0.0166 (8)	0.0177 (9)	0.0011 (7)	0.0076 (8)	0.0009 (7)

Geometric parameters (Å, º) top

Br1—C9	1.9022 (19)	C5—H5B	0.99
O1—C1	1.226 (2)	C6—C11	1.399 (3)
C1—C2	1.463 (3)	C6—C7	1.404 (3)
C1—C5	1.514 (3)	C7—C8	1.383 (3)
C2—C3	1.346 (3)	C7—H7	0.95
C2—H2	0.95	C8—C9	1.384 (3)
C3—C6	1.473 (3)	C8—H8	0.95
C3—C4	1.509 (2)	C9—C10	1.386 (3)
C4—C5	1.538 (3)	C10—C11	1.391 (3)
C4—H4A	0.99	C10—H10	0.95
C4—H4B	0.99	C11—H11	0.95
C5—H5A	0.99

O1—C1—C2	126.57 (17)	H5A—C5—H5B	108.8
O1—C1—C5	125.55 (17)	C11—C6—C7	118.25 (17)
C2—C1—C5	107.87 (16)	C11—C6—C3	120.99 (16)
C3—C2—C1	110.76 (16)	C7—C6—C3	120.72 (16)
C3—C2—H2	124.6	C8—C7—C6	120.64 (18)
C1—C2—H2	124.6	C8—C7—H7	119.7
C2—C3—C6	126.28 (17)	C6—C7—H7	119.7
C2—C3—C4	111.66 (16)	C7—C8—C9	119.44 (18)
C6—C3—C4	122.05 (16)	C7—C8—H8	120.3
C3—C4—C5	104.63 (15)	C9—C8—H8	120.3
C3—C4—H4A	110.8	C8—C9—C10	121.80 (18)
C5—C4—H4A	110.8	C8—C9—Br1	118.07 (14)
C3—C4—H4B	110.8	C10—C9—Br1	120.11 (14)
C5—C4—H4B	110.8	C9—C10—C11	118.16 (17)
H4A—C4—H4B	108.9	C9—C10—H10	120.9
C1—C5—C4	105.03 (15)	C11—C10—H10	120.9
C1—C5—H5A	110.7	C10—C11—C6	121.68 (17)
C4—C5—H5A	110.7	C10—C11—H11	119.2
C1—C5—H5B	110.7	C6—C11—H11	119.2
C4—C5—H5B	110.7

O1—C1—C2—C3	−179.48 (18)	C4—C3—C6—C7	176.47 (16)
C5—C1—C2—C3	−0.5 (2)	C11—C6—C7—C8	1.1 (3)
C1—C2—C3—C6	177.94 (16)	C3—C6—C7—C8	−176.78 (16)
C1—C2—C3—C4	−1.0 (2)	C6—C7—C8—C9	0.3 (3)
C2—C3—C4—C5	2.0 (2)	C7—C8—C9—C10	−1.3 (3)
C6—C3—C4—C5	−176.98 (16)	C7—C8—C9—Br1	177.38 (14)
O1—C1—C5—C4	−179.30 (18)	C8—C9—C10—C11	0.9 (3)
C2—C1—C5—C4	1.7 (2)	Br1—C9—C10—C11	−177.78 (13)
C3—C4—C5—C1	−2.16 (19)	C9—C10—C11—C6	0.5 (3)
C2—C3—C6—C11	179.84 (18)	C7—C6—C11—C10	−1.5 (3)
C4—C3—C6—C11	−1.3 (3)	C3—C6—C11—C10	176.34 (16)
C2—C3—C6—C7	−2.4 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O1ⁱ	0.95	2.58	3.465 (2)	154
C7—H7···O1ⁱ	0.95	2.58	3.484 (3)	158
C10—H10···O1ⁱⁱ	0.95	2.52	3.377 (2)	150

Symmetry codes: (i) −x+1, −y, −z+1; (ii) x−1, −y+1/2, z−1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O1ⁱ	0.95	2.58	3.465 (2)	154
C7—H7···O1ⁱ	0.95	2.58	3.484 (3)	158
C10—H10···O1ⁱⁱ	0.95	2.52	3.377 (2)	150

Symmetry codes: (i) −x+1, −y, −z+1; (ii) x−1, −y+1/2, z−1/2.

Acknowledgements

We acknowledge funding support from the Defense Threat Reduction Agency (DTRA) - Joint Science and Technology Office for Chemcial and Biological Defense (MIPR No. HDTRA13964). The Air Force Office of Scientific Research is also acknowledged for partial financial support. ES was supported through the National Research Council (NRC) Research Associate Program.

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ISSN: 2056-9890

Volume 70| Part 6| June 2014| Pages o692-o693

doi:10.1107/S160053681401071X

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