(2E)-1-(4-Chloro­phen­yl)-3-[4-(propan-2-yl)phen­yl]prop-2-en-1-one

Narayana, B.; Salian, V.V.; Sarojini, B.K.; Jasinski, J.P.

doi:10.1107/S1600536814015281

organic compounds

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Volume 70| Part 8| August 2014| Page o855

doi:10.1107/S1600536814015281

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(2E)-1-(4-Chlorophenyl)-3-[4-(propan-2-yl)phenyl]prop-2-en-1-one

Badiadka Narayana,^a Vinutha V. Salian,^a Balladka K. Sarojini ^b and Jerry P. Jasinski ^c ^*

^aDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri 574 199, India, ^bDepartment of Studies in Chemistry, Industrial Chemistry Section, Mangalore University, Mangalagangotri 574 199, India, and ^cDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA
^*Correspondence e-mail: jjasinski@keene.edu

Edited by G. Smith, Queensland University of Technology, Australia (Received 26 May 2014; accepted 30 June 2014; online 5 July 2014)

In the title compound, C₁₈H₁₇ClO, the dihedral angle between the benzene rings is 53.5 (1)°. The mean plane of the prop-2-en-1-one group is twisted by 24.5 (8) and 33.5 (3)° from the chloro- and propanyl-substituted rings, respectively.

Keywords: crystal structure.

CCDC reference: 1011011

Related literature

For the non-linear optical properties of the chalcones, see: Sarojini et al. (2006 ); Poornesh et al. (2009 ) and for their biological activity, see: Nielsen et al. (1998 ); Mai et al. (2014 ); Insuasty et al. (2013 ). For related structures, see: Jasinski et al. (2009 , 2012 ); Butcher et al. (2007 ); Harrison et al. (2006 ). For standard bond lengths, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₈H₁₇ClO
M_r = 284.76
Monoclinic, P 2₁ /c
a = 8.8547 (5) Å
b = 5.8455 (3) Å
c = 28.8034 (17) Å
β = 97.396 (6)°
V = 1478.46 (14) Å³
Z = 4
Cu Kα radiation
μ = 2.21 mm⁻¹
T = 173 K
0.41 × 0.32 × 0.14 mm

Data collection

Agilent Eos Gemini diffractometer
Absorption correction: multi-scan CrysAlis PRO and CrysAlis RED (Agilent, 2012 ) T_min = 0.370, T_max = 1.000
8687 measured reflections
2868 independent reflections
2269 reflections with I > 2σ(I)
R_int = 0.023

Refinement

R[F² > 2σ(F²)] = 0.093
wR(F²) = 0.286
S = 1.04
2868 reflections
183 parameters
H-atom parameters constrained
Δρ_max = 0.87 e Å⁻³
Δρ_min = −0.44 e Å⁻³

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Agilent, 2012); program(s) used to solve structure: SUPERFLIP (Palatinus et al., 2012 ); program(s) used to refine structure: SHELXL2012 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009 ); software used to prepare material for publication: OLEX2.

Supporting information

CCDC reference: 1011011

Crystal structure: contains datablock I. DOI: 10.1107/S1600536814015281/zs2302sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814015281/zs2302Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814015281/zs2302Isup3.cml

checkCIF report

Comment top

Chalcones are an important class of natural compounds and have been widely applied as synthons in synthetic organic chemistry. The nonlinear optical properties of the different chalcone derivatives have been reported (Sarojini et al., 2006; Poornesh et al., 2009). These α,β-unsaturated ketones also possess a wide variety of biological activities, including anti-leishmanial (Nielsen et al., 1998), anticancer (Mai et al., 2014) and antitumor activity (Insuasty et al., 2013). The crystal structures of some chalcone derivatives viz., a second polymorph of (2E)-1-(4-fluorophenyl)-3-(3, 4, 5-trimethoxyphenyl)prop-2-en- 1-one, (2E)-1-(3,4-dichlorophenyl)-3-(2-hydroxyphenyl)prop-2-en- 1-one (Jasinski et al., 2009, 2012), (2E)-1-(2,4-dichlorophenyl)-3-[4-(methylsulfanyl)phenyl] prop-2-en-1-one (Butcher et al., 2007) and 2-bromo-1-chlorophenyl-3-(4-methoxyphenyl) prop-2-en-1-one (Harrison et al., 2006) have been reported. In view of the importance of chalcone derivatives, we report herein the crystal structure of the title compound, C₁₈H₁₇ClO.

In the title compound, the dihedral angle between the mean planes of the phenyl rings is 53.5 (1)°. The mean plane of the prop-2-en-1-one group (C1/C2/O1/C8) is twisted away from the two phenyl rings by 24.5 (8)° (C2–C7) and 33.5 (3)° (C10–C15) (Fig. 1). Bond lengths are in normal ranges (Allen et al., 1987). No classical hyrogen bonds are observed.

Related literature top

For the non-linear optical properties of the chalcones, see: Sarojini et al. (2006); Poornesh et al. (2009)and for their biological activity, see: Nielsen et al. (1998); Mai et al. (2014); Insuasty et al. (2013). For related structures, see: Jasinski et al. (2009, 2012); Butcher et al. (2007); Harrison et al. (2006). For standard bond lengths, see: Allen et al. (1987).

Experimental top

To a mixture of cuminaldehyde (1.5 mL, 0.01 mol) and 4-chloroacetophenone (1.3 mL, 0.01 mol) in ethanol (50 mL), 15 mL of 10 % sodium hydroxide solution was added and stirred at 273–278 K for 3 h (Fig. 2). The precipitate formed was collected by filtration. Single crystals were grown from ethanol by slow the evaporation method (m.p.: 343–345 K).

Computing details top

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO (Agilent, 2012); data reduction: CrysAlis RED (Agilent, 2012); program(s) used to solve structure: SUPERFLIP (Palatinus et al., 2012); program(s) used to refine structure: SHELXL2012 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Figures top

	Fig. 1. ORTEP drawing of C₁₈H₁₇ClO, showing the atom labeling scheme, with 30% probability displacement ellipsoids.
	Fig. 2. Synthesis of C₁₈H₁₇ClO.

(2E)-1-(4-Chlorophenyl)-3-[4-(propan-2-yl)phenyl]prop-2-en-1-one top

Crystal data top

C₁₈H₁₇ClO	D_x = 1.279 Mg m⁻³
M_r = 284.76	Melting point = 343–345 K
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.54184 Å
a = 8.8547 (5) Å	Cell parameters from 2529 reflections
b = 5.8455 (3) Å	θ = 4.6–72.0°
c = 28.8034 (17) Å	µ = 2.21 mm⁻¹
β = 97.396 (6)°	T = 173 K
V = 1478.46 (14) Å³	Prism, colourless
Z = 4	0.41 × 0.32 × 0.14 mm
F(000) = 600

Data collection top

Agilent Eos Gemini diffractometer	2868 independent reflections
Radiation source: Enhance (Cu) X-ray Source	2269 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
Detector resolution: 16.0416 pixels mm^-1	θ_max = 72.1°, θ_min = 5.0°
ω scans	h = −10→10
Absorption correction: multi-scan CrysAlis PRO and CrysAlis RED (Agilent, 2012)	k = −7→6
T_min = 0.370, T_max = 1.000	l = −35→29
8687 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.093	H-atom parameters constrained
wR(F²) = 0.286	w = 1/[σ²(F_o²) + (0.1595P)² + 1.6733P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
2868 reflections	Δρ_max = 0.87 e Å⁻³
183 parameters	Δρ_min = −0.44 e Å⁻³
0 restraints

Crystal data top

C₁₈H₁₇ClO	V = 1478.46 (14) Å³
M_r = 284.76	Z = 4
Monoclinic, P2₁/c	Cu Kα radiation
a = 8.8547 (5) Å	µ = 2.21 mm⁻¹
b = 5.8455 (3) Å	T = 173 K
c = 28.8034 (17) Å	0.41 × 0.32 × 0.14 mm
β = 97.396 (6)°

Data collection top

Agilent Eos Gemini diffractometer	2868 independent reflections
Absorption correction: multi-scan CrysAlis PRO and CrysAlis RED (Agilent, 2012)	2269 reflections with I > 2σ(I)
T_min = 0.370, T_max = 1.000	R_int = 0.023
8687 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.093	0 restraints
wR(F²) = 0.286	H-atom parameters constrained
S = 1.04	Δρ_max = 0.87 e Å⁻³
2868 reflections	Δρ_min = −0.44 e Å⁻³
183 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	U_iso*/U_eq
Cl1	−0.25150 (13)	0.8390 (2)	0.33097 (5)	0.0819 (5)
O1	0.2335 (4)	0.2755 (5)	0.48768 (11)	0.0695 (8)
C1	0.2184 (5)	0.4826 (7)	0.48178 (13)	0.0576 (10)
C2	0.1070 (4)	0.5752 (6)	0.44409 (14)	0.0550 (9)
C3	0.0602 (5)	0.4451 (7)	0.40431 (15)	0.0625 (10)
H3	0.1034	0.2981	0.4012	0.075*
C4	−0.0468 (5)	0.5249 (8)	0.36970 (16)	0.0675 (11)
H4	−0.0755	0.4358	0.3424	0.081*
C5	−0.1133 (5)	0.7368 (8)	0.37462 (16)	0.0638 (11)
C6	−0.0724 (5)	0.8693 (8)	0.41294 (17)	0.0691 (12)
H6	−0.1192	1.0137	0.4161	0.083*
C7	0.0386 (5)	0.7896 (7)	0.44713 (16)	0.0677 (12)
H7	0.0696	0.8833	0.4736	0.081*
C8	0.3018 (5)	0.6508 (8)	0.51427 (16)	0.0671 (11)
H8	0.3047	0.8073	0.5055	0.080*
C9	0.3719 (5)	0.5833 (8)	0.55524 (17)	0.0676 (11)
H9	0.3598	0.4270	0.5630	0.081*
C10	0.4664 (5)	0.7227 (8)	0.59013 (16)	0.0652 (11)
C11	0.5252 (5)	0.9341 (8)	0.57874 (15)	0.0676 (11)
H11	0.5026	0.9925	0.5478	0.081*
C12	0.6155 (5)	1.0579 (7)	0.61201 (14)	0.0612 (10)
H12	0.6546	1.2016	0.6038	0.073*
C13	0.6505 (4)	0.9774 (6)	0.65722 (13)	0.0529 (9)
C14	0.5907 (5)	0.7645 (7)	0.66783 (15)	0.0613 (10)
H14	0.6116	0.7055	0.6987	0.074*
C15	0.5034 (5)	0.6414 (7)	0.63453 (17)	0.0694 (12)
H15	0.4671	0.4953	0.6424	0.083*
C16	0.7492 (5)	1.1144 (7)	0.69393 (15)	0.0614 (10)
H16	0.7841	1.2548	0.6786	0.074*
C17	0.6624 (6)	1.1896 (8)	0.73356 (16)	0.0706 (12)
H17A	0.5750	1.2834	0.7209	0.106*
H17B	0.7299	1.2794	0.7563	0.106*
H17C	0.6265	1.0545	0.7490	0.106*
C18	0.8911 (5)	0.9757 (10)	0.7134 (2)	0.0834 (14)
H18A	0.8599	0.8406	0.7299	0.125*
H18B	0.9583	1.0709	0.7351	0.125*
H18C	0.9454	0.9273	0.6875	0.125*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0684 (8)	0.0788 (8)	0.1002 (10)	−0.0040 (5)	0.0173 (6)	0.0148 (6)
O1	0.0799 (19)	0.0492 (16)	0.0811 (19)	−0.0082 (14)	0.0161 (15)	−0.0158 (14)
C1	0.064 (2)	0.053 (2)	0.061 (2)	−0.0177 (17)	0.0283 (18)	−0.0123 (17)
C2	0.059 (2)	0.0465 (19)	0.065 (2)	−0.0154 (16)	0.0298 (18)	−0.0121 (16)
C3	0.073 (3)	0.047 (2)	0.071 (2)	−0.0081 (18)	0.022 (2)	−0.0150 (18)
C4	0.081 (3)	0.055 (2)	0.068 (2)	−0.010 (2)	0.016 (2)	−0.0130 (19)
C5	0.059 (2)	0.058 (2)	0.079 (3)	−0.0136 (18)	0.029 (2)	−0.001 (2)
C6	0.066 (3)	0.053 (2)	0.092 (3)	−0.0027 (19)	0.027 (2)	−0.011 (2)
C7	0.077 (3)	0.053 (2)	0.078 (3)	−0.013 (2)	0.028 (2)	−0.022 (2)
C8	0.071 (3)	0.061 (2)	0.073 (3)	−0.011 (2)	0.022 (2)	−0.010 (2)
C9	0.067 (2)	0.059 (2)	0.081 (3)	−0.009 (2)	0.027 (2)	−0.013 (2)
C10	0.065 (2)	0.057 (2)	0.076 (3)	−0.0096 (19)	0.016 (2)	−0.0076 (19)
C11	0.076 (3)	0.064 (3)	0.065 (2)	−0.021 (2)	0.015 (2)	0.0024 (19)
C12	0.066 (2)	0.055 (2)	0.065 (2)	−0.0173 (18)	0.0215 (19)	0.0001 (18)
C13	0.0468 (18)	0.0501 (19)	0.066 (2)	−0.0054 (15)	0.0211 (16)	−0.0031 (16)
C14	0.060 (2)	0.053 (2)	0.071 (2)	−0.0070 (18)	0.0101 (18)	0.0066 (18)
C15	0.072 (3)	0.050 (2)	0.086 (3)	−0.0152 (19)	0.006 (2)	0.013 (2)
C16	0.060 (2)	0.057 (2)	0.069 (2)	−0.0092 (18)	0.0171 (19)	−0.0049 (18)
C17	0.079 (3)	0.066 (3)	0.069 (3)	0.002 (2)	0.020 (2)	−0.008 (2)
C18	0.053 (2)	0.092 (4)	0.105 (4)	−0.004 (2)	0.010 (2)	−0.021 (3)

Geometric parameters (Å, º) top

Cl1—C5	1.743 (5)	C10—C15	1.364 (6)
O1—C1	1.228 (5)	C11—H11	0.9500
C1—C2	1.472 (6)	C11—C12	1.372 (6)
C1—C8	1.486 (6)	C12—H12	0.9500
C2—C3	1.393 (5)	C12—C13	1.382 (6)
C2—C7	1.400 (6)	C13—C14	1.401 (5)
C3—H3	0.9500	C13—C16	1.512 (5)
C3—C4	1.366 (6)	C14—H14	0.9500
C4—H4	0.9500	C14—C15	1.358 (6)
C4—C5	1.386 (6)	C15—H15	0.9500
C5—C6	1.359 (6)	C16—H16	1.0000
C6—H6	0.9500	C16—C17	1.521 (6)
C6—C7	1.379 (7)	C16—C18	1.538 (7)
C7—H7	0.9500	C17—H17A	0.9800
C8—H8	0.9500	C17—H17B	0.9800
C8—C9	1.321 (7)	C17—H17C	0.9800
C9—H9	0.9500	C18—H18A	0.9800
C9—C10	1.469 (6)	C18—H18B	0.9800
C10—C11	1.396 (6)	C18—H18C	0.9800

O1—C1—C2	121.0 (3)	C12—C11—H11	119.9
O1—C1—C8	121.9 (4)	C11—C12—H12	119.4
C2—C1—C8	116.9 (4)	C11—C12—C13	121.2 (4)
C3—C2—C1	120.4 (4)	C13—C12—H12	119.4
C3—C2—C7	117.0 (4)	C12—C13—C14	117.6 (4)
C7—C2—C1	122.5 (4)	C12—C13—C16	121.2 (3)
C2—C3—H3	119.4	C14—C13—C16	121.2 (4)
C4—C3—C2	121.3 (4)	C13—C14—H14	119.6
C4—C3—H3	119.4	C15—C14—C13	120.9 (4)
C3—C4—H4	120.2	C15—C14—H14	119.6
C3—C4—C5	119.6 (4)	C10—C15—H15	119.2
C5—C4—H4	120.2	C14—C15—C10	121.6 (4)
C4—C5—Cl1	120.0 (4)	C14—C15—H15	119.2
C6—C5—Cl1	118.7 (4)	C13—C16—H16	108.0
C6—C5—C4	121.3 (4)	C13—C16—C17	112.1 (3)
C5—C6—H6	120.7	C13—C16—C18	110.3 (4)
C5—C6—C7	118.6 (4)	C17—C16—H16	108.0
C7—C6—H6	120.7	C17—C16—C18	110.3 (4)
C2—C7—H7	118.9	C18—C16—H16	108.0
C6—C7—C2	122.1 (4)	C16—C17—H17A	109.5
C6—C7—H7	118.9	C16—C17—H17B	109.5
C1—C8—H8	119.9	C16—C17—H17C	109.5
C9—C8—C1	120.2 (4)	H17A—C17—H17B	109.5
C9—C8—H8	119.9	H17A—C17—H17C	109.5
C8—C9—H9	116.3	H17B—C17—H17C	109.5
C8—C9—C10	127.3 (4)	C16—C18—H18A	109.5
C10—C9—H9	116.3	C16—C18—H18B	109.5
C11—C10—C9	121.8 (4)	C16—C18—H18C	109.5
C15—C10—C9	119.7 (4)	H18A—C18—H18B	109.5
C15—C10—C11	118.5 (4)	H18A—C18—H18C	109.5
C10—C11—H11	119.9	H18B—C18—H18C	109.5
C12—C11—C10	120.3 (4)

Cl1—C5—C6—C7	−179.1 (3)	C8—C9—C10—C11	−16.7 (7)
O1—C1—C2—C3	−25.1 (5)	C8—C9—C10—C15	165.8 (5)
O1—C1—C2—C7	152.0 (4)	C9—C10—C11—C12	−178.8 (4)
O1—C1—C8—C9	−13.1 (6)	C9—C10—C15—C14	179.8 (4)
C1—C2—C3—C4	177.8 (4)	C10—C11—C12—C13	0.1 (7)
C1—C2—C7—C6	−176.0 (4)	C11—C10—C15—C14	2.3 (7)
C1—C8—C9—C10	176.1 (4)	C11—C12—C13—C14	0.1 (6)
C2—C1—C8—C9	162.2 (4)	C11—C12—C13—C16	−179.6 (4)
C2—C3—C4—C5	−1.7 (6)	C12—C13—C14—C15	0.9 (6)
C3—C2—C7—C6	1.1 (6)	C12—C13—C16—C17	115.4 (4)
C3—C4—C5—Cl1	−179.3 (3)	C12—C13—C16—C18	−121.2 (4)
C3—C4—C5—C6	1.1 (6)	C13—C14—C15—C10	−2.1 (7)
C4—C5—C6—C7	0.5 (6)	C14—C13—C16—C17	−64.3 (5)
C5—C6—C7—C2	−1.7 (6)	C14—C13—C16—C18	59.0 (5)
C7—C2—C3—C4	0.6 (6)	C15—C10—C11—C12	−1.3 (7)
C8—C1—C2—C3	159.6 (4)	C16—C13—C14—C15	−179.4 (4)
C8—C1—C2—C7	−23.4 (5)

Experimental details

Crystal data
Chemical formula	C₁₈H₁₇ClO
M_r	284.76
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	173
a, b, c (Å)	8.8547 (5), 5.8455 (3), 28.8034 (17)
β (°)	97.396 (6)
V (Å³)	1478.46 (14)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	2.21
Crystal size (mm)	0.41 × 0.32 × 0.14

Data collection
Diffractometer	Agilent Eos Gemini diffractometer
Absorption correction	Multi-scan CrysAlis PRO and CrysAlis RED (Agilent, 2012)
T_min, T_max	0.370, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	8687, 2868, 2269
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.093, 0.286, 1.04
No. of reflections	2868
No. of parameters	183
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.87, −0.44

Computer programs: CrysAlis PRO (Agilent, 2012), CrysAlis RED (Agilent, 2012), SUPERFLIP (Palatinus et al., 2012), SHELXL2012 (Sheldrick, 2008), OLEX2 (Dolomanov et al., 2009).

Acknowledgements

BN thanks the UGC for financial assistance through a BSR one-time grant for the purchase of chemicals. VVS thanks the DST for financial assistance through a PURSE grant. JPJ acknowledges the NSF–MRI program (grant No. CHE-1039027) for funds to purchase the X-ray diffractometer.

References

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