Crystal structure of (E)-1-(3-chloro­phen­yl)-3-(furan-2-yl)prop-2-en-1-one

Zingales, S.K.; Wallace, M.Z.; Padgett, C.W.

doi:10.1107/S2056989015016266

organic compounds

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doi:10.1107/S2056989015016266

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Crystal structure of (E)-1-(3-chlorophenyl)-3-(furan-2-yl)prop-2-en-1-one

Sarah K. Zingales,^a ^* Maya Z. Wallace ^a and Clifford W. Padgett ^a

^aArmstrong State University, Department of Chemistry and Physics, 11935 Abercorn St., Savannah, GA 31419, USA
^*Correspondence e-mail: sarah.zingales@armstrong.edu

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 20 August 2015; accepted 31 August 2015; online 12 September 2015)

The title compound, C₁₃H₉ClO₂, exhibits a non-planar geometry; the furan ring being inclined to the benzene ring by 50.52 (16)°. In the crystal, molecules stack along the a axis; however, there are no significant intermolecular interactions present.

Keywords: crystal structure; chalcone.

CCDC reference: 1421581

1. Related literature

For the synthesis of the title compound, see: HanLee et al. (2011 ). For the syntheses of related compounds, see: Inokuma et al. (2009 ).

2. Experimental

2.1. Crystal data

C₁₃H₉ClO₂
M_r = 232.67
Monoclinic, P 2₁ /c
a = 7.186 (8) Å
b = 25.77 (3) Å
c = 5.774 (6) Å
β = 94.734 (10)°
V = 1066 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.34 mm⁻¹
T = 173 K
0.30 × 0.30 × 0.10 mm

2.2. Data collection

Rigaku XtaLAB mini diffractometer
Absorption correction: multi-scan (REQAB; Rigaku, 1998 ) T_min = 0.832, T_max = 0.967
11328 measured reflections
2461 independent reflections
1672 reflections with F² > 2.0σ(F²)
R_int = 0.080

2.3. Refinement

R[F² > 2σ(F²)] = 0.054
wR(F²) = 0.128
S = 1.07
2461 reflections
145 parameters
H-atom parameters constrained
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.33 e Å⁻³

Data collection: CrystalClear-SM Expert (Rigaku, 2011 ); cell refinement: CrystalClear-SM Expert; data reduction: CrystalClear-SM Expert; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: CrystalStructure (Rigaku, 2011); software used to prepare material for publication: CrystalStructure.

Supporting information

CCDC reference: 1421581

Crystal structure: contains datablocks Global, I. DOI: 10.1107/S2056989015016266/su5196sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2056989015016266/su5196Isup2.hkl

Supporting information file. DOI: 10.1107/S2056989015016266/su5196Isup3.tif

Supporting information file. DOI: 10.1107/S2056989015016266/su5196Isup4.cml

checkCIF report

Chemical context top

The title compound is a chalcone analog that is currently being studied for its potential anticancer activity [unpublished results]. Its synthesis and NMR characteristics have been reported (HanLee et al. 2011), but its crystal structure has not been reported until now.

Synthesis and crystallization top

The title compound was synthesized by an aldol condensation reaction. 3-furaldehyde (1 mmol) and 3-chloroacetophenone (1 mmol) were dissolved in ethanol (5 ml). A NaOH solution (5 M, 1 mL) was added and the reaction mixture was stirred until a precipitate formed. The reaction mixture was cooled in an ice bath for 20 min. The solids formed were filtered off and recrystallized from MeOH/H₂O (1:1, v:v). Slow evaporation of a solution of the title compound in MeOH gave pale brown crystals.

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 1. The H atoms were included in calculated positions and treated as riding atoms: C—H = 0.95 Å with U_iso(H) = 1.2U_eq(C).

Related literature top

For the synthesis of the title compound, see: HanLee et al. (2011). For the syntheses of related compounds, see: Inokuma et al. (2009).

Computing details top

Data collection: CrystalClear-SM Expert (Rigaku, 2011); cell refinement: CrystalClear-SM Expert (Rigaku, 2011); data reduction: CrystalClear-SM Expert (Rigaku, 2011); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: CrystalStructure (Rigaku, 2011); software used to prepare material for publication: CrystalStructure (Rigaku, 2011).

Figures top

Fig. 1. A view of the molecular structure of the title compound, with atom labelling. Displacement ellipsoids are drawn at the 50% probability level.

(E)-1-(3-Chlorophenyl)-3-(furan-2-yl)prop-2-en-1-one top

Crystal data top

C₁₃H₉ClO₂	F(000) = 480.00
M_r = 232.67	D_x = 1.450 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71075 Å
Hall symbol: -P 2ybc	Cell parameters from 2235 reflections
a = 7.186 (8) Å	θ = 2.4–27.5°
b = 25.77 (3) Å	µ = 0.34 mm⁻¹
c = 5.774 (6) Å	T = 173 K
β = 94.734 (10)°	Prism, colorless
V = 1066 (2) Å³	0.30 × 0.30 × 0.10 mm
Z = 4

Data collection top

Rigaku XtaLAB mini diffractometer	1672 reflections with F² > 2.0σ(F²)
Detector resolution: 6.827 pixels mm^-1	R_int = 0.080
ω scans	θ_max = 27.6°
Absorption correction: multi-scan (REQAB; Rigaku, 1998)	h = −9→9
T_min = 0.832, T_max = 0.967	k = −33→33
11328 measured reflections	l = −7→7
2461 independent reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.128	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0293P)² + 0.6811P] where P = (F_o² + 2F_c²)/3
2461 reflections	(Δ/σ)_max < 0.001
145 parameters	Δρ_max = 0.29 e Å⁻³
0 restraints	Δρ_min = −0.33 e Å⁻³
Primary atom site location: structure-invariant direct methods

Crystal data top

C₁₃H₉ClO₂	V = 1066 (2) Å³
M_r = 232.67	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.186 (8) Å	µ = 0.34 mm⁻¹
b = 25.77 (3) Å	T = 173 K
c = 5.774 (6) Å	0.30 × 0.30 × 0.10 mm
β = 94.734 (10)°

Data collection top

Rigaku XtaLAB mini diffractometer	2461 independent reflections
Absorption correction: multi-scan (REQAB; Rigaku, 1998)	1672 reflections with F² > 2.0σ(F²)
T_min = 0.832, T_max = 0.967	R_int = 0.080
11328 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.054	0 restraints
wR(F²) = 0.128	H-atom parameters constrained
S = 1.07	Δρ_max = 0.29 e Å⁻³
2461 reflections	Δρ_min = −0.33 e Å⁻³
145 parameters

Special details top

Refinement. Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F². R-factor (gt) are based on F. The threshold expression of F² > 2.0 σ(F²) is used only for calculating R-factor (gt).

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

	x	y	z	U_iso*/U_eq
Cl1	0.25413 (11)	0.29816 (3)	0.35320 (13)	0.0404 (3)
O1	0.2759 (3)	0.50459 (7)	0.3133 (4)	0.0385 (6)
O2	0.3111 (3)	0.71261 (7)	0.9248 (4)	0.0395 (5)
C1	0.2650 (4)	0.49620 (10)	0.5220 (5)	0.0295 (6)
C2	0.2198 (4)	0.44238 (10)	0.6022 (5)	0.0263 (6)
C3	0.2537 (4)	0.40038 (10)	0.4594 (5)	0.0271 (6)
C4	0.2074 (4)	0.35117 (10)	0.5274 (5)	0.0289 (6)
C5	0.1236 (4)	0.34244 (11)	0.7323 (5)	0.0335 (7)
C6	0.0897 (4)	0.38439 (11)	0.8733 (5)	0.0334 (7)
C7	0.1396 (4)	0.43435 (11)	0.8108 (5)	0.0304 (7)
C8	0.2914 (4)	0.53727 (10)	0.6976 (5)	0.0293 (6)
C9	0.2727 (4)	0.58734 (10)	0.6361 (5)	0.0271 (6)
C10	0.3055 (4)	0.63097 (10)	0.7933 (5)	0.0275 (6)
C11	0.2624 (4)	0.68115 (11)	0.7414 (5)	0.0338 (7)
C12	0.3882 (5)	0.68125 (12)	1.0974 (5)	0.0369 (7)
C13	0.3873 (4)	0.63144 (11)	1.0275 (5)	0.0327 (7)
H3	0.3082	0.4057	0.3168	0.0325*
H5	0.0902	0.3083	0.7751	0.0402*
H6	0.0320	0.3790	1.0135	0.0400*
H7	0.1190	0.4628	0.9100	0.0365*
H8	0.3220	0.5284	0.8559	0.0352*
H9	0.2353	0.5948	0.4780	0.0325*
H11	0.2058	0.6927	0.5960	0.0406*
H12	0.4359	0.6930	1.2466	0.0443*
H13	0.4323	0.6023	1.1162	0.0393*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0503 (5)	0.0258 (4)	0.0454 (5)	0.0004 (4)	0.0067 (4)	−0.0059 (3)
O1	0.0601 (15)	0.0292 (11)	0.0266 (11)	0.0010 (10)	0.0055 (10)	0.0005 (9)
O2	0.0520 (13)	0.0243 (11)	0.0418 (12)	−0.0012 (10)	0.0011 (10)	−0.0057 (9)
C1	0.0321 (15)	0.0254 (14)	0.0308 (15)	0.0027 (12)	0.0017 (12)	−0.0006 (12)
C2	0.0285 (14)	0.0268 (14)	0.0231 (13)	0.0008 (12)	−0.0017 (11)	−0.0017 (11)
C3	0.0289 (15)	0.0297 (15)	0.0224 (14)	−0.0024 (12)	0.0002 (11)	−0.0026 (11)
C4	0.0294 (15)	0.0258 (14)	0.0308 (15)	0.0019 (12)	−0.0023 (12)	−0.0024 (12)
C5	0.0319 (16)	0.0331 (16)	0.0347 (16)	−0.0032 (13)	−0.0026 (13)	0.0051 (12)
C6	0.0314 (16)	0.0391 (17)	0.0302 (15)	−0.0022 (13)	0.0065 (12)	0.0035 (13)
C7	0.0311 (15)	0.0339 (16)	0.0262 (14)	0.0024 (13)	0.0023 (12)	−0.0014 (12)
C8	0.0351 (16)	0.0285 (14)	0.0239 (14)	0.0001 (13)	−0.0001 (11)	0.0000 (11)
C9	0.0272 (14)	0.0294 (14)	0.0247 (14)	0.0002 (12)	0.0022 (11)	−0.0014 (11)
C10	0.0287 (14)	0.0271 (14)	0.0275 (14)	−0.0018 (12)	0.0062 (11)	−0.0008 (11)
C11	0.0397 (17)	0.0307 (15)	0.0304 (15)	−0.0047 (13)	−0.0009 (13)	−0.0035 (12)
C12	0.0419 (18)	0.0388 (17)	0.0295 (15)	0.0016 (15)	−0.0007 (13)	−0.0049 (13)
C13	0.0338 (16)	0.0335 (16)	0.0307 (15)	0.0020 (14)	0.0008 (12)	0.0002 (12)

Geometric parameters (Å, º) top

Cl1—C4	1.746 (3)	C4—C5	1.389 (5)
O1—C1	1.233 (4)	C5—C6	1.387 (5)
O2—C11	1.357 (4)	C6—C7	1.392 (5)
O2—C12	1.365 (4)	C8—C9	1.342 (4)
C1—C2	1.506 (4)	C9—C10	1.452 (4)
C1—C8	1.467 (4)	C10—C11	1.357 (4)
C2—C3	1.394 (4)	C10—C13	1.429 (4)
C2—C7	1.393 (4)	C12—C13	1.346 (5)
C3—C4	1.377 (4)

C11—O2—C12	106.2 (3)	C4—C5—C6	118.9 (3)
O1—C1—C2	119.7 (3)	C5—C6—C7	120.5 (3)
O1—C1—C8	122.3 (3)	C2—C7—C6	119.7 (3)
C2—C1—C8	118.1 (3)	C1—C8—C9	120.4 (3)
C1—C2—C3	118.7 (3)	C8—C9—C10	124.9 (3)
C1—C2—C7	121.2 (3)	C9—C10—C11	125.3 (3)
C3—C2—C7	120.1 (3)	C9—C10—C13	129.1 (3)
C2—C3—C4	119.2 (3)	C11—C10—C13	105.6 (3)
Cl1—C4—C3	119.6 (3)	O2—C11—C10	110.9 (3)
Cl1—C4—C5	118.8 (3)	O2—C12—C13	110.7 (3)
C3—C4—C5	121.6 (3)	C10—C13—C12	106.5 (3)

Experimental details

Crystal data
Chemical formula	C₁₃H₉ClO₂
M_r	232.67
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	173
a, b, c (Å)	7.186 (8), 25.77 (3), 5.774 (6)
β (°)	94.734 (10)
V (Å³)	1066 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.34
Crystal size (mm)	0.30 × 0.30 × 0.10

Data collection
Diffractometer	Rigaku XtaLAB mini diffractometer
Absorption correction	Multi-scan (REQAB; Rigaku, 1998)
T_min, T_max	0.832, 0.967
No. of measured, independent and observed [F² > 2.0σ(F²)] reflections	11328, 2461, 1672
R_int	0.080
(sin θ/λ)_max (Å⁻¹)	0.651

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.054, 0.128, 1.07
No. of reflections	2461
No. of parameters	145
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.33

Computer programs: CrystalClear-SM Expert (Rigaku, 2011), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), CrystalStructure (Rigaku, 2011).

Acknowledgements

MZW is grateful for the financial support of an ASU Undergraduate Research Grant and SKZ for an ASU Research and Scholarship Grant.

References

HanLee, I.-S., Jeon, H.-J. & Lee, C.-K. (2011). Bull. Korean Chem. Soc. 32, 687–692. CrossRef Google Scholar
Rigaku (1998). REQAB. Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku (2011). CrystalClear-SM Expert and CrystalStructure. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Inokuma, T., Nagamoto, Y., Sakamoto, S., Miyabe, H., Takasu, K. & Takemoto, Y. (2009). Heterocycles, 79, 573–582. CAS Google Scholar

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CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 71| Part 10| October 2015| Page o707

doi:10.1107/S2056989015016266

Open

access