(E)-1-(4-Chloro­phen­yl)-3-(4-methyl­phen­yl)prop-2-en-1-one

Fun, H.-K.; Jebas, S.R.; Patil, P.S.; Dharmaprakash, S.M.

doi:10.1107/S160053680801324X

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 6| June 2008| Page o1038

doi:10.1107/S160053680801324X

Open

access

(E)-1-(4-Chlorophenyl)-3-(4-methylphenyl)prop-2-en-1-one

Hoong-Kun Fun,^a ^* Samuel Robinson Jebas,^a ‡ P. S. Patil ^b and S. M. Dharmaprakash ^c

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, ^bDepartment of Studies in Physics, Mangalore University, Mangalagangotri, Mangalore 574 199, India, and ^cDepartment of Studies in Physics, Mangalore University, Mangalagangotri, Mangalore 574 199, India.
^*Correspondence e-mail: hkfun@usm.my

(Received 30 April 2008; accepted 5 May 2008; online 10 May 2008)

The title compound, C₁₆H₁₃ClO, adopts an E configuration with respect to the C=C double bond of the propenone unit. The dihedral angle between the two benzene rings is 45.9 (2)°. In the crystal structure, molecules are arranged into sheets parallel to the ac plane and the sheets are stacked along the b axis. This arrangement is stabilized by weak intermolecular C—H⋯π interactions involving both aromatic rings.

Related literature

For applications of chalcones in non-linear optics, see: Agrinskaya et al. (1999 ). For related structures, see: Patil, Dharmaprakash et al. (2007 ); Patil, Fun et al. (2007 ); Patil, Rosli et al. (2007 ).

Experimental

Crystal data

C₁₆H₁₃ClO
M_r = 256.71
Monoclinic, P 2₁ /c
a = 15.2632 (3) Å
b = 14.0146 (3) Å
c = 5.8487 (1) Å
β = 92.154 (1)°
V = 1250.20 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.29 mm⁻¹
T = 100.0 (1) K
0.34 × 0.18 × 0.05 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.908, T_max = 0.986
15494 measured reflections
3661 independent reflections
2534 reflections with I > 2σ(I)
R_int = 0.054

Refinement

R[F² > 2σ(F²)] = 0.053
wR(F²) = 0.129
S = 1.04
3661 reflections
164 parameters
H-atom parameters constrained
Δρ_max = 0.41 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9⋯O1	0.93	2.50	2.820 (2)	100
C5—H5⋯Cg1ⁱ	0.93	2.98	3.525	119
C2—H2⋯Cg2ⁱⁱ	0.93	2.93	3.563	127
C14—H14⋯Cg2ⁱⁱⁱ	0.93	2.80	3.495	132
Symmetry codes: (i) $[x, -y-{\script{1\over 2}}, z-{\script{3\over 2}}]$ ; (ii) -x, -y, -z+1; (iii) $[x, -y-{\script{1\over 2}}, z-{\script{1\over 2}}]$ . Cg1 and Cg2 are the centroids of the C1–C6 and C10–C15 rings, respectively.

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680801324X/ci2595sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680801324X/ci2595Isup2.hkl

checkCIF report

Comment top

Recently, significant progress has been achieved in the growth of noncentrosymmetric crystals for second harmonic generation (SHG), mostly that of chalcone derivatives substituted with different donor/acceptor substituents (Agrinskaya et al., 1999; Patil, Dharmaprakash et al., 2007; Patil, Fun et al., 2007; Patil, Rosli et al., 2007). Herein we report the crystal structure of the title compound.

The title molecule (Fig.1) exhibits an E configuration with respect to the C8?C9 double bond, with the C7—C8—C9—C10 torsion angle being -175.3 (2)°. The bond lengths and angles are comparable to those observed in related structures (Patil, Dharmaprakash et al., 2007; Patil, Fun et al., 2007; Patil, Rosli et al., 2007). The dihedral angle between the two benzene rings is 45.9 (1)°.

In the molecular structure, an intramolecular C—H···O hydrogen bond generates an S(5) ring motif. In the crystal structure, the molecules are arranged into sheets parallel to the ac plane and the sheets are stacked along the b axis (Fig. 2). This arrangement is stabilized by weak intermolecular C—H···π interactions involving both aromatic rings, Table 1.

Related literature top

For applications of chalcones in non-linear optics, see: Agrinskaya et al. (1999). For related structures, see: Patil, Dharmaprakash et al. (2007); Patil, Fun et al. (2007); Patil, Rosli et al. (2007). Cg1 and Cg2 are the centroids of the C1–C6 and C10–C15 rings, respectively.

Experimental top

The title compound was synthesized by the condensation of p-tolualdehyde (0.01 mol) with 4-chloroacetophenone (0.01 mol) in methanol (60 ml) in the presence of a catalytic amount of sodium hydroxide solution (5 ml, 30%). After stirring for 6 h, the contents of the flask were poured into ice-cold water (500 ml) and left to stand for 12 h. The resulting crude solid was filtered and dried. Single crystals suitable for X-ray diffraction were grown by slow evaporation of an acetone solution at room temperature.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2 (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003).

Figures top

	Fig. 1. The molecular structure of the title compound, showing 50% probability displacement ellipsoids and the atom-numbering scheme. The intramolecular hydrogen bond is shown as a dashed line.
	Fig. 2. The crystal packing of the title compound, viewed along the c axis. Hydrogen bonds are shown as dashed lines.

(E)-1-(4-Chlorophenyl)-3-(4-methylphenyl)prop-2-en-1-one top

Crystal data top

C₁₆H₁₃ClO	F(000) = 536
M_r = 256.71	D_x = 1.364 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2431 reflections
a = 15.2632 (3) Å	θ = 2.7–29.9°
b = 14.0146 (3) Å	µ = 0.29 mm⁻¹
c = 5.8487 (1) Å	T = 100 K
β = 92.154 (1)°	Plate, colourless
V = 1250.20 (4) Å³	0.34 × 0.18 × 0.05 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	3661 independent reflections
Radiation source: fine-focus sealed tube	2534 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.055
ϕ and ω scans	θ_max = 30.1°, θ_min = 1.3°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −21→21
T_min = 0.908, T_max = 0.986	k = −19→19
15494 measured reflections	l = −6→8

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.129	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0438P)² + 0.9337P] where P = (F_o² + 2F_c²)/3
3661 reflections	(Δ/σ)_max = 0.001
164 parameters	Δρ_max = 0.41 e Å⁻³
0 restraints	Δρ_min = −0.27 e Å⁻³

Crystal data top

C₁₆H₁₃ClO	V = 1250.20 (4) Å³
M_r = 256.71	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 15.2632 (3) Å	µ = 0.29 mm⁻¹
b = 14.0146 (3) Å	T = 100 K
c = 5.8487 (1) Å	0.34 × 0.18 × 0.05 mm
β = 92.154 (1)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	3661 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	2534 reflections with I > 2σ(I)
T_min = 0.908, T_max = 0.986	R_int = 0.055
15494 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.053	0 restraints
wR(F²) = 0.129	H-atom parameters constrained
S = 1.04	Δρ_max = 0.41 e Å⁻³
3661 reflections	Δρ_min = −0.27 e Å⁻³
164 parameters

Special details top

Experimental. The data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.

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	−0.37993 (3)	0.37197 (4)	0.72301 (10)	0.02546 (15)
O1	0.01956 (10)	0.38013 (12)	0.3019 (2)	0.0258 (4)
C1	−0.12084 (13)	0.40835 (14)	0.7779 (3)	0.0177 (4)
H1	−0.0797	0.4295	0.8878	0.021*
C2	−0.20925 (13)	0.40915 (14)	0.8251 (3)	0.0178 (4)
H2	−0.2279	0.4322	0.9643	0.021*
C3	−0.26921 (13)	0.37513 (14)	0.6615 (3)	0.0178 (4)
C4	−0.24374 (13)	0.34215 (14)	0.4505 (4)	0.0192 (4)
H4	−0.2850	0.3196	0.3425	0.023*
C5	−0.15563 (13)	0.34352 (14)	0.4044 (3)	0.0178 (4)
H5	−0.1375	0.3225	0.2630	0.021*
C6	−0.09327 (12)	0.37615 (14)	0.5676 (3)	0.0166 (4)
C7	0.00093 (13)	0.37789 (14)	0.5041 (4)	0.0183 (4)
C8	0.06927 (13)	0.37523 (15)	0.6898 (3)	0.0190 (4)
H8	0.0541	0.3596	0.8377	0.023*
C9	0.15291 (13)	0.39512 (14)	0.6470 (3)	0.0170 (4)
H9	0.1641	0.4150	0.4992	0.020*
C10	0.22861 (13)	0.38904 (13)	0.8071 (3)	0.0160 (4)
C11	0.31013 (13)	0.42159 (14)	0.7374 (3)	0.0172 (4)
H11	0.3144	0.4494	0.5939	0.021*
C12	0.38450 (13)	0.41295 (14)	0.8791 (4)	0.0187 (4)
H12	0.4378	0.4358	0.8299	0.022*
C13	0.38079 (13)	0.37070 (14)	1.0938 (3)	0.0180 (4)
C14	0.29931 (13)	0.33856 (14)	1.1634 (3)	0.0174 (4)
H14	0.2953	0.3101	1.3063	0.021*
C15	0.22434 (13)	0.34813 (14)	1.0242 (3)	0.0167 (4)
H15	0.1708	0.3271	1.0757	0.020*
C16	0.46114 (13)	0.35970 (16)	1.2478 (4)	0.0241 (5)
H16A	0.5117	0.3523	1.1567	0.036*
H16B	0.4549	0.3044	1.3428	0.036*
H16C	0.4682	0.4153	1.3425	0.036*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0154 (2)	0.0311 (3)	0.0299 (3)	0.0011 (2)	0.00166 (19)	−0.0017 (2)
O1	0.0214 (7)	0.0393 (9)	0.0169 (8)	−0.0012 (7)	0.0016 (6)	0.0010 (7)
C1	0.0183 (9)	0.0173 (9)	0.0171 (10)	−0.0015 (8)	−0.0029 (8)	0.0006 (8)
C2	0.0194 (9)	0.0177 (10)	0.0162 (10)	0.0015 (8)	0.0004 (8)	−0.0004 (8)
C3	0.0154 (9)	0.0166 (9)	0.0214 (10)	0.0007 (8)	0.0010 (8)	0.0031 (8)
C4	0.0195 (10)	0.0183 (10)	0.0195 (10)	0.0000 (8)	−0.0047 (8)	−0.0006 (8)
C5	0.0214 (10)	0.0171 (9)	0.0148 (10)	0.0022 (8)	−0.0013 (8)	−0.0002 (8)
C6	0.0161 (9)	0.0150 (9)	0.0185 (10)	0.0014 (8)	−0.0011 (7)	0.0032 (8)
C7	0.0179 (9)	0.0178 (9)	0.0192 (10)	0.0005 (8)	0.0009 (8)	−0.0001 (8)
C8	0.0196 (10)	0.0214 (10)	0.0161 (10)	0.0019 (8)	0.0004 (8)	0.0023 (8)
C9	0.0194 (9)	0.0165 (10)	0.0152 (10)	0.0023 (8)	0.0017 (8)	0.0010 (8)
C10	0.0162 (9)	0.0147 (9)	0.0171 (10)	0.0035 (7)	0.0013 (7)	−0.0015 (8)
C11	0.0205 (10)	0.0168 (10)	0.0144 (10)	0.0018 (8)	0.0022 (8)	0.0012 (8)
C12	0.0153 (9)	0.0197 (10)	0.0212 (11)	−0.0007 (8)	0.0037 (8)	0.0010 (8)
C13	0.0171 (9)	0.0177 (9)	0.0191 (10)	0.0012 (8)	−0.0012 (8)	−0.0021 (8)
C14	0.0207 (10)	0.0185 (10)	0.0129 (9)	−0.0004 (8)	0.0010 (8)	0.0006 (8)
C15	0.0160 (9)	0.0167 (10)	0.0175 (10)	−0.0010 (8)	0.0033 (8)	−0.0018 (8)
C16	0.0175 (10)	0.0309 (12)	0.0235 (11)	0.0004 (9)	−0.0030 (8)	0.0027 (9)

Geometric parameters (Å, º) top

Cl1—C3	1.742 (2)	C9—C10	1.462 (3)
O1—C7	1.227 (2)	C9—H9	0.93
C1—C2	1.388 (3)	C10—C15	1.397 (3)
C1—C6	1.390 (3)	C10—C11	1.400 (3)
C1—H1	0.93	C11—C12	1.385 (3)
C2—C3	1.384 (3)	C11—H11	0.93
C2—H2	0.93	C12—C13	1.391 (3)
C3—C4	1.387 (3)	C12—H12	0.93
C4—C5	1.382 (3)	C13—C14	1.397 (3)
C4—H4	0.93	C13—C16	1.502 (3)
C5—C6	1.399 (3)	C14—C15	1.386 (3)
C5—H5	0.93	C14—H14	0.93
C6—C7	1.499 (3)	C15—H15	0.93
C7—C8	1.478 (3)	C16—H16A	0.96
C8—C9	1.340 (3)	C16—H16B	0.96
C8—H8	0.93	C16—H16C	0.96

C2—C1—C6	120.50 (19)	C10—C9—H9	116.4
C2—C1—H1	119.7	C15—C10—C11	118.07 (18)
C6—C1—H1	119.7	C15—C10—C9	122.91 (18)
C3—C2—C1	118.86 (19)	C11—C10—C9	118.95 (18)
C3—C2—H2	120.6	C12—C11—C10	120.97 (18)
C1—C2—H2	120.6	C12—C11—H11	119.5
C2—C3—C4	122.00 (18)	C10—C11—H11	119.5
C2—C3—Cl1	119.19 (16)	C11—C12—C13	121.12 (19)
C4—C3—Cl1	118.81 (15)	C11—C12—H12	119.4
C5—C4—C3	118.44 (19)	C13—C12—H12	119.4
C5—C4—H4	120.8	C12—C13—C14	117.82 (18)
C3—C4—H4	120.8	C12—C13—C16	121.66 (18)
C4—C5—C6	120.91 (19)	C14—C13—C16	120.52 (18)
C4—C5—H5	119.5	C15—C14—C13	121.47 (19)
C6—C5—H5	119.5	C15—C14—H14	119.3
C1—C6—C5	119.27 (18)	C13—C14—H14	119.3
C1—C6—C7	122.63 (18)	C14—C15—C10	120.54 (18)
C5—C6—C7	118.07 (18)	C14—C15—H15	119.7
O1—C7—C8	121.77 (18)	C10—C15—H15	119.7
O1—C7—C6	119.90 (18)	C13—C16—H16A	109.5
C8—C7—C6	118.32 (18)	C13—C16—H16B	109.5
C9—C8—C7	120.57 (19)	H16A—C16—H16B	109.5
C9—C8—H8	119.7	C13—C16—H16C	109.5
C7—C8—H8	119.7	H16A—C16—H16C	109.5
C8—C9—C10	127.16 (19)	H16B—C16—H16C	109.5
C8—C9—H9	116.4

C6—C1—C2—C3	1.6 (3)	C6—C7—C8—C9	−166.97 (19)
C1—C2—C3—C4	−1.3 (3)	C7—C8—C9—C10	−175.30 (19)
C1—C2—C3—Cl1	177.78 (15)	C8—C9—C10—C15	9.1 (3)
C2—C3—C4—C5	0.1 (3)	C8—C9—C10—C11	−173.9 (2)
Cl1—C3—C4—C5	−179.00 (15)	C15—C10—C11—C12	0.4 (3)
C3—C4—C5—C6	0.9 (3)	C9—C10—C11—C12	−176.80 (18)
C2—C1—C6—C5	−0.7 (3)	C10—C11—C12—C13	0.8 (3)
C2—C1—C6—C7	177.19 (18)	C11—C12—C13—C14	−1.0 (3)
C4—C5—C6—C1	−0.6 (3)	C11—C12—C13—C16	179.17 (19)
C4—C5—C6—C7	−178.54 (18)	C12—C13—C14—C15	0.0 (3)
C1—C6—C7—O1	−155.5 (2)	C16—C13—C14—C15	179.90 (19)
C5—C6—C7—O1	22.4 (3)	C13—C14—C15—C10	1.1 (3)
C1—C6—C7—C8	25.5 (3)	C11—C10—C15—C14	−1.3 (3)
C5—C6—C7—C8	−156.65 (18)	C9—C10—C15—C14	175.76 (18)
O1—C7—C8—C9	14.0 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···O1	0.93	2.50	2.820 (2)	100
C5—H5···Cg1ⁱ	0.93	2.98	3.525	119
C2—H2···Cg2ⁱⁱ	0.93	2.93	3.563	127
C14—H14···Cg2ⁱⁱⁱ	0.93	2.80	3.495	132

Symmetry codes: (i) x, −y−1/2, z−3/2; (ii) −x, −y, −z+1; (iii) x, −y−1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₃ClO
M_r	256.71
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	15.2632 (3), 14.0146 (3), 5.8487 (1)
β (°)	92.154 (1)
V (Å³)	1250.20 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.29
Crystal size (mm)	0.34 × 0.18 × 0.05

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.908, 0.986
No. of measured, independent and observed [I > 2σ(I)] reflections	15494, 3661, 2534
R_int	0.055
(sin θ/λ)_max (Å⁻¹)	0.705

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.053, 0.129, 1.04
No. of reflections	3661
No. of parameters	164
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.41, −0.27

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···O1	0.93	2.50	2.820 (2)	100
C5—H5···Cg1ⁱ	0.93	2.98	3.525	119
C2—H2···Cg2ⁱⁱ	0.93	2.93	3.563	127
C14—H14···Cg2ⁱⁱⁱ	0.93	2.80	3.495	132

Symmetry codes: (i) x, −y−1/2, z−3/2; (ii) −x, −y, −z+1; (iii) x, −y−1/2, z−1/2.

Footnotes

‡Permanent address : Department of Physics, Karunya University, Karunya Nagar, Coimbatore 641 114, India.

Acknowledgements

HKF and SRJ thank the Malaysian Government and Universiti Sains Malaysia for the Science Fund grant No. 305/PFIZIK/613312. SRJ thanks Universiti Sains Malaysia for a post-doctoral research fellowship. PSP thanks the DRDO, Government of India, for a Senior Research Fellowship (SRF). This work was also supported by the Department of Science and Technology (DST), Government of India, grant No. SR/S2/LOP-17/2006.

References

Agrinskaya, N. V., Lukoshkin, V. A., Kudryavtsev, V. V., Nosova, G. I., Solovskaya, N. A. & Yakimanski, A. V. (1999). Phys. Solid State, 41, 1914–1917. Web of Science CrossRef CAS Google Scholar
Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Patil, P. S., Dharmaprakash, S. M., Ramakrishna, K., Fun, H.-K., Sai Santosh Kumar, R. & Rao, D. N. (2007). J. Cryst. Growth, 303, 520–524. Web of Science CrossRef CAS Google Scholar
Patil, P. S., Fun, H.-K., Chantrapromma, S. & Dharmaprakash, S. M. (2007). Acta Cryst. E63, o2497–o2498. Web of Science CSD CrossRef IUCr Journals Google Scholar
Patil, P. S., Rosli, M. M., Fun, H.-K., Razak, I. A. & Dharmaprakash, S. M. (2007). Acta Cryst. E63, o3238. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar