1-(4-Chloro-phen-yl)-3-(3,4-dimethyl-phen-yl)prop-2-en-1-one.

The title compound, C(17)H(15)ClO, was prepared from 3,4-dimethyl-benzaldehyde and 4-chloro-hypnone 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 = 270.74

Triclinic,

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[F 2 > 2σ(F 2)] = 0.061

wR(F 2) = 0.188

S = 1.08

3141 reflections

172 parameters

H-atom parameters constrained

Δρmax = 0.54 e Å−3

Δρmin = −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.

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

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810031880/hb5576Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C17H15ClO	Z = 2
Mr = 270.74	F(000) = 284
Triclinic, P1	Dx = 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

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

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(Fo2) + (0.1287P)2 + 0.0873P] where P = (Fo2 + 2Fc2)/3
3141 reflections	(Δ/σ)max < 0.001
172 parameters	Δρmax = 0.54 e Å−3
0 restraints	Δρmin = −0.52 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)