(2E)-1-(4-Chloro-phen-yl)-3-[4-(propan-2-yl)phen-yl]prop-2-en-1-one.

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.

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 = 284.76

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.093

wR(F 2) = 0.286

S = 1.04

2868 reflections

183 parameters

H-atom parameters constrained

Δρmax = 0.87 e Å−3

Δρmin = −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.

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

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

Click here for additional data file.

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

CCDC reference: 1011011

Additional supporting information: crystallographic information; 3D view; checkCIF report

C18H17ClO	Dx = 1.279 Mg m−3
Mr = 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

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

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(Fo2) + (0.1595P)2 + 1.6733P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
2868 reflections	Δρmax = 0.87 e Å−3
183 parameters	Δρmin = −0.44 e Å−3
0 restraints

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)