1-(4-Chloro­phen­yl)-3-(3,4-dimethyl­phen­yl)prop-2-en-1-one

Guo, M.

doi:10.1107/S1600536810031880

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 66| Part 9| September 2010| Page o2302

https://doi.org/10.1107/S1600536810031880

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1-(4-Chlorophenyl)-3-(3,4-dimethylphenyl)prop-2-en-1-one

Meng Guo ^a ^*

^aMicroscale Science Institute, Weifang University, Weifang 261061, People's Republic of China
^*Correspondence e-mail: ffjian2008@163.com

(Received 24 July 2010; accepted 9 August 2010; online 18 August 2010)

The title compound, C₁₇H₁₅ClO, was prepared from 3,4-dimethylbenzaldehyde and 4-chlorohypnone by Aldol condensation. The dihedral angle formed by the two benzene rings is 48.91 (8)°. Only van der Waals forces affect the packing.

Related literature

For background to the aplications of chalcones, see: Anto et al. (1994 ); Hsieh et al. (1998 ). For a related structure, see: Zhou (2010 ).

Experimental

Crystal data

C₁₇H₁₅ClO
M_r = 270.74
Triclinic, $[P \overline 1]$
a = 5.9621 (12) Å
b = 7.7369 (15) Å
c = 15.513 (3) Å
α = 98.30 (3)°
β = 99.96 (3)°
γ = 95.23 (3)°
V = 692.5 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.26 mm⁻¹
T = 293 K
0.25 × 0.20 × 0.18 mm

Data collection

Bruker SMART CCD diffractometer
6689 measured reflections
3141 independent reflections
2643 reflections with I > 2σ(I)
R_int = 0.030

Refinement

R[F² > 2σ(F²)] = 0.061
wR(F²) = 0.188
S = 1.08
3141 reflections
172 parameters
H-atom parameters constrained
Δρ_max = 0.54 e Å⁻³
Δρ_min = −0.52 e Å⁻³

Data collection: SMART (Bruker, 1997 ); cell refinement: SAINT (Bruker, 1997); 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); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810031880/hb5576sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810031880/hb5576Isup2.hkl

checkCIF report

Comment top

Among flavonoids, chalcones have been identified as interesting compounds having multiple biological actions which include antiinflammatory (Hsieh et al.,1998) and antioxidant (Anto et al.,1994). As part of our search for new biologically active compounds we synthesized the title compound (I) and report its crystal structure herein.

In the crystal structure of compound(I)(Fig.1),the dihedral angle between the two benzene rings(C1—C6) and (C10—C15) is 48.91 (8)°. All of the bond lengths and bond angles are in normal ranges and comparable to those in a related structure (Zhou,2010).

Related literature top

For background to the aplications of chalcones, see: Anto et al. (1994); Hsieh et al. (1998). For a related structure, see: Zhou (2010).

Experimental top

A mixture of the 4-chlorohypnone (0.01 mol) and 3,4-dimethylbenzaldehyde(0.01 mol) and 10% NaOH (10 ml) was stirred in ethanol (30 ml) for 3 h to afford the title compound (yield 65%). Yellow bars of (I) were obtailed by recrystallization from ethyl acetate at room temperature.

Structure description top

For background to the aplications of chalcones, see: Anto et al. (1994); Hsieh et al. (1998). For a related structure, see: Zhou (2010).

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of (I) with displacement ellipsoids drawn at the 30% probability level.

1-(4-Chlorophenyl)-3-(3,4-dimethylphenyl)prop-2-en-1-one top

Crystal data top

C₁₇H₁₅ClO	Z = 2
M_r = 270.74	F(000) = 284
Triclinic, P1	D_x = 1.299 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.9621 (12) Å	Cell parameters from 2643 reflections
b = 7.7369 (15) Å	θ = 3.2–27.5°
c = 15.513 (3) Å	µ = 0.26 mm⁻¹
α = 98.30 (3)°	T = 293 K
β = 99.96 (3)°	Bar, yellow
γ = 95.23 (3)°	0.25 × 0.20 × 0.18 mm
V = 692.5 (2) Å³

Data collection top

Bruker SMART CCD diffractometer	2643 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.030
Graphite monochromator	θ_max = 27.5°, θ_min = 3.2°
phi and ω scans	h = −7→7
6689 measured reflections	k = −10→10
3141 independent reflections	l = −20→18

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)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.188	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.1287P)² + 0.0873P] where P = (F_o² + 2F_c²)/3
3141 reflections	(Δ/σ)_max < 0.001
172 parameters	Δρ_max = 0.54 e Å⁻³
0 restraints	Δρ_min = −0.52 e Å⁻³

Crystal data top

C₁₇H₁₅ClO	γ = 95.23 (3)°
M_r = 270.74	V = 692.5 (2) Å³
Triclinic, P1	Z = 2
a = 5.9621 (12) Å	Mo Kα radiation
b = 7.7369 (15) Å	µ = 0.26 mm⁻¹
c = 15.513 (3) Å	T = 293 K
α = 98.30 (3)°	0.25 × 0.20 × 0.18 mm
β = 99.96 (3)°

Data collection top

Bruker SMART CCD diffractometer	2643 reflections with I > 2σ(I)
6689 measured reflections	R_int = 0.030
3141 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.061	0 restraints
wR(F²) = 0.188	H-atom parameters constrained
S = 1.08	Δρ_max = 0.54 e Å⁻³
3141 reflections	Δρ_min = −0.52 e Å⁻³
172 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.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	U_iso*/U_eq
Cl1	0.06653 (10)	0.43200 (7)	−0.40023 (3)	0.0645 (2)
C2	0.2286 (3)	0.4248 (2)	−0.22733 (12)	0.0442 (4)
H2A	0.3675	0.4759	−0.2370	0.053*
C15	0.3097 (3)	0.2253 (2)	0.26373 (11)	0.0398 (4)
H15A	0.1822	0.2763	0.2774	0.048*
C10	0.3326 (3)	0.1916 (2)	0.17512 (11)	0.0372 (4)
C1	0.0394 (3)	0.3865 (2)	−0.29529 (11)	0.0419 (4)
C9	0.1543 (3)	0.2354 (2)	0.10668 (11)	0.0405 (4)
H9A	0.0194	0.2644	0.1245	0.049*
C7	−0.0361 (3)	0.2764 (2)	−0.04009 (11)	0.0417 (4)
C6	−0.1707 (3)	0.3131 (2)	−0.28266 (12)	0.0476 (4)
H6A	−0.2959	0.2877	−0.3293	0.057*
O1	−0.2265 (2)	0.2775 (2)	−0.02091 (9)	0.0582 (4)
C11	0.5261 (3)	0.1151 (2)	0.15544 (12)	0.0425 (4)
H11A	0.5490	0.0942	0.0972	0.051*
C8	0.1647 (3)	0.2382 (2)	0.02181 (12)	0.0449 (4)
H8A	0.2987	0.2161	0.0013	0.054*
C4	−0.0022 (3)	0.3133 (2)	−0.12946 (10)	0.0369 (4)
C3	0.2072 (3)	0.3857 (2)	−0.14451 (11)	0.0425 (4)
H3A	0.3340	0.4081	−0.0985	0.051*
C12	0.6825 (3)	0.0710 (2)	0.22314 (12)	0.0445 (4)
H12A	0.8084	0.0181	0.2092	0.053*
C14	0.4693 (3)	0.1859 (2)	0.33241 (11)	0.0412 (4)
C13	0.6579 (3)	0.1031 (2)	0.31155 (12)	0.0417 (4)
C5	−0.1902 (3)	0.2784 (2)	−0.19930 (12)	0.0441 (4)
H5A	−0.3309	0.2311	−0.1895	0.053*
C17	0.4398 (4)	0.2300 (4)	0.42722 (13)	0.0626 (6)
H17A	0.5647	0.1938	0.4657	0.094*
H17B	0.2977	0.1697	0.4343	0.094*
H17C	0.4381	0.3546	0.4422	0.094*
C16	0.8291 (4)	0.0483 (3)	0.38260 (15)	0.0594 (5)
H16A	0.9448	−0.0063	0.3562	0.089*
H16B	0.7525	−0.0338	0.4119	0.089*
H16C	0.8994	0.1499	0.4250	0.089*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0855 (4)	0.0709 (4)	0.0412 (3)	0.0036 (3)	0.0171 (2)	0.0203 (2)
C2	0.0418 (8)	0.0477 (9)	0.0442 (9)	−0.0002 (7)	0.0126 (7)	0.0093 (7)
C15	0.0371 (7)	0.0445 (8)	0.0399 (8)	0.0054 (6)	0.0118 (6)	0.0086 (7)
C10	0.0372 (7)	0.0368 (7)	0.0384 (8)	0.0012 (6)	0.0094 (6)	0.0085 (6)
C1	0.0527 (9)	0.0393 (8)	0.0353 (8)	0.0056 (7)	0.0108 (7)	0.0087 (6)
C9	0.0418 (8)	0.0423 (8)	0.0391 (8)	0.0037 (6)	0.0106 (6)	0.0094 (6)
C7	0.0433 (8)	0.0462 (8)	0.0369 (8)	0.0062 (6)	0.0105 (6)	0.0067 (7)
C6	0.0450 (8)	0.0537 (10)	0.0407 (9)	0.0009 (7)	−0.0002 (7)	0.0092 (7)
O1	0.0451 (7)	0.0882 (10)	0.0464 (7)	0.0088 (6)	0.0163 (5)	0.0177 (7)
C11	0.0449 (8)	0.0433 (8)	0.0411 (9)	0.0041 (7)	0.0150 (7)	0.0052 (7)
C8	0.0457 (8)	0.0541 (10)	0.0383 (8)	0.0103 (7)	0.0119 (7)	0.0116 (7)
C4	0.0385 (7)	0.0377 (7)	0.0353 (8)	0.0056 (6)	0.0084 (6)	0.0058 (6)
C3	0.0371 (7)	0.0493 (9)	0.0390 (8)	0.0010 (6)	0.0049 (6)	0.0053 (7)
C12	0.0410 (8)	0.0414 (8)	0.0527 (10)	0.0064 (6)	0.0139 (7)	0.0056 (7)
C14	0.0397 (8)	0.0463 (8)	0.0387 (8)	0.0012 (6)	0.0108 (6)	0.0090 (7)
C13	0.0384 (8)	0.0386 (8)	0.0475 (9)	0.0010 (6)	0.0058 (7)	0.0102 (7)
C5	0.0374 (8)	0.0494 (9)	0.0443 (9)	−0.0002 (7)	0.0058 (7)	0.0093 (7)
C17	0.0549 (10)	0.0958 (16)	0.0399 (9)	0.0154 (10)	0.0116 (8)	0.0130 (10)
C16	0.0561 (10)	0.0655 (12)	0.0585 (12)	0.0147 (9)	0.0040 (9)	0.0194 (10)

Geometric parameters (Å, º) top

Cl1—C1	1.7455 (17)	C11—H11A	0.9300
C2—C1	1.382 (3)	C8—H8A	0.9300
C2—C3	1.386 (3)	C4—C3	1.392 (2)
C2—H2A	0.9300	C4—C5	1.394 (2)
C15—C14	1.389 (2)	C3—H3A	0.9300
C15—C10	1.394 (2)	C12—C13	1.394 (2)
C15—H15A	0.9300	C12—H12A	0.9300
C10—C11	1.403 (2)	C14—C13	1.406 (2)
C10—C9	1.467 (2)	C14—C17	1.505 (3)
C1—C6	1.385 (3)	C13—C16	1.504 (2)
C9—C8	1.332 (2)	C5—H5A	0.9300
C9—H9A	0.9300	C17—H17A	0.9600
C7—O1	1.222 (2)	C17—H17B	0.9600
C7—C8	1.481 (2)	C17—H17C	0.9600
C7—C4	1.499 (2)	C16—H16A	0.9600
C6—C5	1.380 (3)	C16—H16B	0.9600
C6—H6A	0.9300	C16—H16C	0.9600
C11—C12	1.383 (3)

C1—C2—C3	118.67 (15)	C5—C4—C7	118.34 (15)
C1—C2—H2A	120.7	C2—C3—C4	120.69 (15)
C3—C2—H2A	120.7	C2—C3—H3A	119.7
C14—C15—C10	122.73 (15)	C4—C3—H3A	119.7
C14—C15—H15A	118.6	C11—C12—C13	122.25 (15)
C10—C15—H15A	118.6	C11—C12—H12A	118.9
C15—C10—C11	118.03 (15)	C13—C12—H12A	118.9
C15—C10—C9	119.14 (14)	C15—C14—C13	118.70 (15)
C11—C10—C9	122.83 (15)	C15—C14—C17	120.56 (15)
C2—C1—C6	122.03 (16)	C13—C14—C17	120.74 (16)
C2—C1—Cl1	118.89 (13)	C12—C13—C14	118.63 (15)
C6—C1—Cl1	119.08 (13)	C12—C13—C16	120.30 (16)
C8—C9—C10	127.04 (15)	C14—C13—C16	121.07 (16)
C8—C9—H9A	116.5	C6—C5—C4	121.01 (16)
C10—C9—H9A	116.5	C6—C5—H5A	119.5
O1—C7—C8	122.36 (16)	C4—C5—H5A	119.5
O1—C7—C4	119.56 (16)	C14—C17—H17A	109.5
C8—C7—C4	118.08 (14)	C14—C17—H17B	109.5
C5—C6—C1	118.51 (15)	H17A—C17—H17B	109.5
C5—C6—H6A	120.7	C14—C17—H17C	109.5
C1—C6—H6A	120.7	H17A—C17—H17C	109.5
C12—C11—C10	119.58 (15)	H17B—C17—H17C	109.5
C12—C11—H11A	120.2	C13—C16—H16A	109.5
C10—C11—H11A	120.2	C13—C16—H16B	109.5
C9—C8—C7	120.28 (16)	H16A—C16—H16B	109.5
C9—C8—H8A	119.9	C13—C16—H16C	109.5
C7—C8—H8A	119.9	H16A—C16—H16C	109.5
C3—C4—C5	119.06 (15)	H16B—C16—H16C	109.5
C3—C4—C7	122.57 (14)

Experimental details

Crystal data
Chemical formula	C₁₇H₁₅ClO
M_r	270.74
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	5.9621 (12), 7.7369 (15), 15.513 (3)
α, β, γ (°)	98.30 (3), 99.96 (3), 95.23 (3)
V (Å³)	692.5 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.26
Crystal size (mm)	0.25 × 0.20 × 0.18

Data collection
Diffractometer	Bruker SMART CCD
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	6689, 3141, 2643
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.061, 0.188, 1.08
No. of reflections	3141
No. of parameters	172
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.54, −0.52

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Acknowledgements

The author thanks the National Natural Science Foundation of Shandong (Y2008B29) and Weifang University for research grants.

References

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