(E)-1-(4-Amino­phen­yl)-3-(2-chloro­phen­yl)prop-2-en-1-one

Fun, H.-K.; Kia, R.; Patil, P.S.; Dharmaprakash, S.M.; Razak, I.A.

doi:10.1107/S1600536808030456

organic compounds

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ISSN: 2056-9890

Volume 64| Part 10| October 2008| Pages o2014-o2015

doi:10.1107/S1600536808030456

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(E)-1-(4-Aminophenyl)-3-(2-chlorophenyl)prop-2-en-1-one

Hoong-Kun Fun,^a ^* Reza Kia,^a P. S. Patil,^b ‡ S. M. Dharmaprakash ^b and Ibrahim Abdul Razak ^a

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bDepartment of Physics, K. L. E. Society's K. L. E. Institute of Technology, Gokul Road, Hubli 590 030, India
^*Correspondence e-mail: hkfun@usm.my

(Received 22 August 2008; accepted 22 September 2008; online 27 September 2008)

The title compound, C₁₅H₁₂ClNO, a substituted chalcone, adopts an E configuration with respect to the C=C bond of the enone unit. The molecule is not planar, as can be seen from the dihedral angle of 28.9 (2)° between the two rings which are twisted from each other. The enone segment of the molecule is not coplanar with the chlorophenyl ring, making a dihedral angle of 23.4 (3)° with it. The amino group is also not coplanar with the ring to which it is bound, making a dihedral angle of 35 (4)°. In the crystal structure, adjacent molecules are linked by N—H⋯O interactions into one-dimensional infinite chains along the c axis, and are further stacked as one-dimensional zigzag chains down the b axis, forming two-dimensional extended networks parallel to the bc plane.

Related literature

For related literature on hydrogen-bond motifs, see Bernstein et al. (1995 ). For bond-length data, see Allen et al. (1987 ). For related structures, see, for example: Patil et al. (2007a ,b ,c ). For background to the applications of substituted chalcones, see, for example: Agrinskaya et al. (1999 ); Gu et al. (2008a ,b ,c ).

Experimental

Crystal data

C₁₅H₁₂ClNO
M_r = 257.71
Monoclinic, P 2₁ /c
a = 22.4670 (19) Å
b = 3.9254 (3) Å
c = 14.5796 (11) Å
β = 107.944 (6)°
V = 1223.26 (17) Å³
Z = 4
Mo Kα radiation
μ = 0.30 mm⁻¹
T = 100.0 (1) K
0.28 × 0.27 × 0.06 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.935, T_max = 0.985
12218 measured reflections
2509 independent reflections
1717 reflections with I > 2σ(I)
R_int = 0.089

Refinement

R[F² > 2σ(F²)] = 0.072
wR(F²) = 0.190
S = 1.13
2509 reflections
171 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.41 e Å⁻³
Δρ_min = −0.40 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯N1ⁱ	0.85 (4)	2.30 (5)	3.098 (6)	158 (4)
N1—H2N1⋯O1ⁱⁱ	0.83 (4)	2.10 (4)	2.923 (5)	171 (4)
Symmetry codes: (i) $[-x, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

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, PARST (Nardelli, 1995 ) and PLATON (Spek, 2003 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808030456/cs2093sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808030456/cs2093Isup2.hkl

checkCIF report

Comment top

Chalcone derivatives exhibit fascinating nonlinear optical properties (Agrinskaya et al., 1999). Among the nonlinear optical applications, optical limiting (OL) has been particularly promising (Gu et al., 2008a; Gu, et al., 2008c). Optical limiters are devices that strongly attenuate intense optical beams while exhibiting high transmittance for low-intensity ambient light levels. This behavior has applications such as the protection of human eyes and optically sensitive equipments. Chalcone derivatives are very good candidates for optical limiting applications (Gu et al., 2008b). As a part of our crystallographic studies (Patil et al., 2007a; Patil et al., 2007b; Patil et al., 2007c), the title compound was synthesized and its crystal structure is reported.

The title compound (I, Fig 1), a substituted chalcone, adopts an E configuration with respect to the C═C bond of the enone unit. Intramolecular C—H···O and C—H···Cl hydrogen bonds involving the enone group generate S(5) ring motifs (Bernstein et al., 1995). The bond lengths are within the normal ranges (Allen et al., 1987). The molecule is not planar, with a maximum deviation from the mean plane of C1–C15/N1/O1 being -1.135 (3) Å for atom Cl1. The amino group is also not coplanar with the phenyl ring to which it is bound. The dihedral angle between the C10–C15 ring and the N1-H1N1-H2N1 plane of the NH₂ group is 34.7(3.7)°. The two phenyl rings are twisted to each other with the dihedral angle of 28.9 (2)°. Adjacent molecules are linked together by N—H···O interactions (Table 1) into 1-D infinite chains along the c axis in the crystal structure (Fig. 2). Such chains are further stacked as 1-D zigzag chains down the b-axis (Fig. 3), too, to form 2-D extended networks parallel to the bc plane.

Related literature top

For related literature on hydrogen-bond motifs, see Bernstein et al. (1995). For bond-length data, see Allen et al. (1987). For related structures, see, for example: Patil et al. (2007a,b,c). For background to the applications of substituted chalcones, see, for example: Agrinskaya et al. (1999); Gu et al. (2008a,b,c).

Experimental top

The compound (I) was synthesized by the condensation of 2-chlorobenzaldehyde (0.01 mol, 1.13 g) with p-aminoacetophenone (0.01 mol, 1.35 g) in methanol (60 ml) in the presence of a catalytic amount of sodium hydroxide solution (5 ml, 30°). After stirring (6 h), the contents of the flask were poured into ice-cold water (500 ml) and left to stand for 5 h. The resulting crude solid was filtered and dried. Crystals suitable for X-ray analysis 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 atomic numbering. Intramolecular interactions are drawn as dashed lines.
	Fig. 2. The crystal packing of (I), viewed down the b-axis, showing 1-D extended chains along the c-axis, and stacking of these chains along the b-axis. Intramolecular and intermolecular interactions are drawn as dashed lines.
	Fig. 3. The crystal packing of (I), viewed down the c-axis, showing 1-D zigzag chains along the b-axis.

(E)-1-(4-Aminophenyl)-3-(2-chlorophenyl)prop-2-en-1-one top

Crystal data top

C₁₅H₁₂ClNO	F(000) = 536
M_r = 257.71	D_x = 1.399 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2522 reflections
a = 22.4670 (19) Å	θ = 2.9–30.2°
b = 3.9254 (3) Å	µ = 0.30 mm⁻¹
c = 14.5796 (11) Å	T = 100 K
β = 107.944 (6)°	Plate, yellow
V = 1223.26 (17) Å³	0.28 × 0.27 × 0.06 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	2509 independent reflections
Radiation source: fine-focus sealed tube	1717 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.090
ϕ and ω scans	θ_max = 26.5°, θ_min = 1.0°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −28→28
T_min = 0.935, T_max = 0.985	k = −4→4
12218 measured reflections	l = −18→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)] = 0.072	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.190	H atoms treated by a mixture of independent and constrained refinement
S = 1.13	w = 1/[σ²(F_o²) + (0.0752P)² + 2.4541P] where P = (F_o² + 2F_c²)/3
2509 reflections	(Δ/σ)_max < 0.001
171 parameters	Δρ_max = 0.41 e Å⁻³
0 restraints	Δρ_min = −0.40 e Å⁻³

Crystal data top

C₁₅H₁₂ClNO	V = 1223.26 (17) Å³
M_r = 257.71	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 22.4670 (19) Å	µ = 0.30 mm⁻¹
b = 3.9254 (3) Å	T = 100 K
c = 14.5796 (11) Å	0.28 × 0.27 × 0.06 mm
β = 107.944 (6)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	2509 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	1717 reflections with I > 2σ(I)
T_min = 0.935, T_max = 0.985	R_int = 0.090
12218 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.072	0 restraints
wR(F²) = 0.190	H atoms treated by a mixture of independent and constrained refinement
S = 1.13	Δρ_max = 0.41 e Å⁻³
2509 reflections	Δρ_min = −0.40 e Å⁻³
171 parameters

Special details top

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

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

	x	y	z	U_iso*/U_eq
Cl1	0.34916 (5)	0.9235 (3)	0.37527 (7)	0.0286 (3)
O1	0.15206 (14)	0.7004 (9)	0.45043 (19)	0.0269 (8)
N1	0.05603 (19)	0.0034 (9)	0.7731 (3)	0.0191 (8)
C1	0.3762 (2)	1.0766 (12)	0.4936 (3)	0.0209 (9)
C2	0.4360 (2)	1.2147 (12)	0.5233 (3)	0.0253 (10)
H2A	0.4594	1.2283	0.4807	0.030*
C3	0.4604 (2)	1.3321 (12)	0.6171 (3)	0.0252 (10)
H3A	0.5006	1.4230	0.6383	0.030*
C4	0.4246 (2)	1.3131 (12)	0.6790 (3)	0.0249 (10)
H4A	0.4407	1.3939	0.7417	0.030*
C5	0.3654 (2)	1.1761 (12)	0.6487 (3)	0.0224 (10)
H5A	0.3422	1.1667	0.6915	0.027*
C6	0.33907 (19)	1.0500 (11)	0.5547 (3)	0.0190 (9)
C7	0.2757 (2)	0.9108 (11)	0.5222 (3)	0.0209 (9)
H7A	0.2566	0.8946	0.4560	0.025*
C8	0.24290 (19)	0.8055 (11)	0.5784 (3)	0.0206 (10)
H8A	0.2606	0.8178	0.6450	0.025*
C9	0.1783 (2)	0.6678 (11)	0.5372 (3)	0.0199 (9)
C10	0.14809 (19)	0.4951 (11)	0.6006 (3)	0.0180 (9)
C11	0.1771 (2)	0.4548 (11)	0.7004 (3)	0.0195 (9)
H11A	0.2172	0.5414	0.7284	0.023*
C12	0.14740 (19)	0.2898 (11)	0.7572 (3)	0.0199 (9)
H12A	0.1675	0.2655	0.8229	0.024*
C13	0.08702 (19)	0.1580 (10)	0.7165 (3)	0.0169 (9)
C14	0.0572 (2)	0.2036 (11)	0.6173 (3)	0.0187 (9)
H14A	0.0168	0.1229	0.5892	0.022*
C15	0.08799 (19)	0.3678 (11)	0.5619 (3)	0.0198 (10)
H15A	0.0678	0.3944	0.4962	0.024*
H1N1	0.027 (2)	−0.133 (12)	0.745 (3)	0.010 (11)*
H2N1	0.081 (2)	−0.044 (11)	0.827 (3)	0.016 (11)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0359 (7)	0.0389 (7)	0.0140 (5)	−0.0011 (6)	0.0120 (4)	0.0004 (5)
O1	0.0299 (17)	0.040 (2)	0.0094 (14)	−0.0045 (15)	0.0036 (12)	0.0015 (13)
N1	0.020 (2)	0.022 (2)	0.0140 (18)	−0.0022 (17)	0.0038 (16)	0.0004 (16)
C1	0.030 (2)	0.021 (2)	0.0133 (18)	0.004 (2)	0.0085 (17)	0.0038 (18)
C2	0.029 (2)	0.027 (3)	0.023 (2)	0.001 (2)	0.0129 (19)	0.0079 (19)
C3	0.022 (2)	0.024 (3)	0.027 (2)	−0.0013 (19)	0.0033 (19)	0.0067 (19)
C4	0.032 (3)	0.024 (3)	0.016 (2)	−0.002 (2)	0.0024 (18)	0.0014 (18)
C5	0.027 (2)	0.025 (3)	0.016 (2)	0.003 (2)	0.0082 (17)	0.0047 (18)
C6	0.026 (2)	0.014 (2)	0.0195 (19)	0.0019 (18)	0.0104 (17)	0.0034 (17)
C7	0.026 (2)	0.024 (2)	0.0122 (18)	0.006 (2)	0.0053 (16)	0.0012 (18)
C8	0.026 (2)	0.023 (2)	0.0130 (19)	0.0019 (19)	0.0060 (17)	0.0011 (17)
C9	0.023 (2)	0.024 (2)	0.0130 (19)	0.0029 (19)	0.0054 (17)	−0.0012 (17)
C10	0.023 (2)	0.020 (2)	0.0116 (18)	0.0030 (18)	0.0066 (16)	−0.0019 (16)
C11	0.021 (2)	0.023 (2)	0.0160 (19)	0.0023 (19)	0.0072 (16)	−0.0017 (18)
C12	0.026 (2)	0.023 (2)	0.0107 (18)	0.0020 (19)	0.0061 (17)	−0.0018 (17)
C13	0.023 (2)	0.015 (2)	0.0150 (19)	0.0039 (18)	0.0097 (16)	−0.0022 (16)
C14	0.021 (2)	0.019 (2)	0.0153 (19)	0.0000 (18)	0.0036 (16)	−0.0037 (17)
C15	0.025 (2)	0.023 (3)	0.0108 (18)	0.0059 (19)	0.0052 (16)	0.0012 (17)

Geometric parameters (Å, º) top

Cl1—C1	1.749 (4)	C7—C8	1.325 (6)
O1—C9	1.226 (5)	C7—H7A	0.9300
N1—C13	1.374 (5)	C8—C9	1.491 (6)
N1—H1N1	0.84 (5)	C8—H8A	0.9300
N1—H2N1	0.83 (5)	C9—C10	1.471 (6)
C1—C2	1.389 (6)	C10—C15	1.386 (6)
C1—C6	1.400 (5)	C10—C11	1.408 (5)
C2—C3	1.387 (6)	C11—C12	1.376 (6)
C2—H2A	0.9300	C11—H11A	0.9300
C3—C4	1.384 (6)	C12—C13	1.401 (6)
C3—H3A	0.9300	C12—H12A	0.9300
C4—C5	1.375 (6)	C13—C14	1.405 (5)
C4—H4A	0.9300	C14—C15	1.375 (6)
C5—C6	1.404 (6)	C14—H14A	0.9300
C5—H5A	0.9300	C15—H15A	0.9300
C6—C7	1.461 (6)

C13—N1—H1N1	116 (3)	C7—C8—C9	121.4 (4)
C13—N1—H2N1	111 (3)	C7—C8—H8A	119.3
H1N1—N1—H2N1	120 (4)	C9—C8—H8A	119.3
C2—C1—C6	122.7 (4)	O1—C9—C10	121.9 (4)
C2—C1—Cl1	116.8 (3)	O1—C9—C8	118.5 (4)
C6—C1—Cl1	120.6 (3)	C10—C9—C8	119.6 (3)
C3—C2—C1	119.2 (4)	C15—C10—C11	117.6 (4)
C3—C2—H2A	120.4	C15—C10—C9	119.3 (3)
C1—C2—H2A	120.4	C11—C10—C9	123.0 (4)
C4—C3—C2	119.5 (4)	C12—C11—C10	121.2 (4)
C4—C3—H3A	120.3	C12—C11—H11A	119.4
C2—C3—H3A	120.3	C10—C11—H11A	119.4
C5—C4—C3	120.7 (4)	C11—C12—C13	120.4 (4)
C5—C4—H4A	119.6	C11—C12—H12A	119.8
C3—C4—H4A	119.6	C13—C12—H12A	119.8
C4—C5—C6	121.7 (4)	N1—C13—C12	120.8 (4)
C4—C5—H5A	119.1	N1—C13—C14	120.4 (4)
C6—C5—H5A	119.1	C12—C13—C14	118.7 (4)
C1—C6—C5	116.1 (4)	C15—C14—C13	119.9 (4)
C1—C6—C7	122.2 (4)	C15—C14—H14A	120.0
C5—C6—C7	121.6 (4)	C13—C14—H14A	120.0
C8—C7—C6	126.0 (4)	C14—C15—C10	122.2 (4)
C8—C7—H7A	117.0	C14—C15—H15A	118.9
C6—C7—H7A	117.0	C10—C15—H15A	118.9

C6—C1—C2—C3	0.0 (7)	C7—C8—C9—C10	168.6 (4)
Cl1—C1—C2—C3	−178.4 (4)	O1—C9—C10—C15	−0.6 (6)
C1—C2—C3—C4	−0.7 (7)	C8—C9—C10—C15	179.9 (4)
C2—C3—C4—C5	0.7 (7)	O1—C9—C10—C11	−179.9 (4)
C3—C4—C5—C6	0.2 (7)	C8—C9—C10—C11	0.7 (6)
C2—C1—C6—C5	0.8 (6)	C15—C10—C11—C12	1.1 (6)
Cl1—C1—C6—C5	179.1 (3)	C9—C10—C11—C12	−179.6 (4)
C2—C1—C6—C7	178.7 (4)	C10—C11—C12—C13	−0.1 (6)
Cl1—C1—C6—C7	−3.0 (6)	C11—C12—C13—N1	−177.7 (4)
C4—C5—C6—C1	−0.9 (6)	C11—C12—C13—C14	−1.2 (6)
C4—C5—C6—C7	−178.8 (4)	N1—C13—C14—C15	178.0 (4)
C1—C6—C7—C8	163.8 (5)	C12—C13—C14—C15	1.5 (6)
C5—C6—C7—C8	−18.5 (7)	C13—C14—C15—C10	−0.5 (7)
C6—C7—C8—C9	179.9 (4)	C11—C10—C15—C14	−0.8 (6)
C7—C8—C9—O1	−10.9 (7)	C9—C10—C15—C14	179.9 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···N1ⁱ	0.85 (4)	2.30 (5)	3.098 (6)	158 (4)
N1—H2N1···O1ⁱⁱ	0.83 (4)	2.10 (4)	2.923 (5)	171 (4)
C7—H7A···Cl1	0.93	2.69	3.081 (5)	106
C7—H7A···O1	0.93	2.45	2.775 (6)	101

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

Experimental details

Crystal data
Chemical formula	C₁₅H₁₂ClNO
M_r	257.71
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	22.4670 (19), 3.9254 (3), 14.5796 (11)
β (°)	107.944 (6)
V (Å³)	1223.26 (17)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.30
Crystal size (mm)	0.28 × 0.27 × 0.06

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.935, 0.985
No. of measured, independent and observed [I > 2σ(I)] reflections	12218, 2509, 1717
R_int	0.090
(sin θ/λ)_max (Å⁻¹)	0.628

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.072, 0.190, 1.13
No. of reflections	2509
No. of parameters	171
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.41, −0.40

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
N1—H1N1···N1ⁱ	0.85 (4)	2.30 (5)	3.098 (6)	158 (4)
N1—H2N1···O1ⁱⁱ	0.83 (4)	2.10 (4)	2.923 (5)	171 (4)
C7—H7A···Cl1	0.9300	2.6900	3.081 (5)	106.00
C7—H7A···O1	0.9300	2.4500	2.775 (6)	101.00

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

Footnotes

‡Additional address: Department of Studies in Physics, Mangalore University, Mangalagangotri, Mangalore 574 199, India.

Acknowledgements

HKF and RK thank the Malaysian Government and Universiti Sains Malaysia for Science Fund grant No. 305/PFIZIK/613312. RK thanks Universiti Sains Malaysia for a postdoctoral research fellowship. IAR and HKF thank Universiti Sains Malaysia and the Malaysian Government for FRGS research grant No. 203/PFIZIK/671064. This work was supported by the Department of Science and Technology (DST), Government of India (grant No. SR/S2/LOP-17/2006).

References

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