1-(2,4-Dichloro­phen­yl)-3-(3,4-dimethoxyphen­yl)prop-2-en-1-one

In the title compound, C₁₇H₁₄Cl₂O₃, the dihedral angle between the benzene rings is 45.42 (15)°. In the crystal structure, mol­ecules form layers parallel to the bc plane, and these are stabilized by inter­molecular C—H...O hydrogen bonds and by π–π inter­actions between the benzene rings with a centroid–centroid distance of 3.848 Å.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C)= 0.004 Å
• R factor = 0.051
• wR factor = 0.153
• Data-to-parameter ratio = 16.8

checkCIF/PLATON results

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Computing details

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 1998); 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).

1-(2,4-Dichlorophenyl)-3-(3,4-dimethoxyphenyl)prop-2-en-1-one

Crystal data

C17H14Cl2O3	Z = 2
Mr = 337.18	F(000) = 348
Triclinic, P1	Dx = 1.506 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 3.8479 (2) Å	Cell parameters from 1123 reflections
b = 12.2341 (6) Å	θ = 1.3–27.5°
c = 16.8454 (7) Å	µ = 0.45 mm^−1
α = 70.487 (3)°	T = 100 K
β = 84.170 (4)°	Plate, yellow
γ = 86.707 (3)°	0.35 × 0.15 × 0.04 mm
V = 743.36 (6) Å^3

Data collection

Bruker SMART APEX2 CCD area-detector diffractometer	3372 independent reflections
Radiation source: fine-focus sealed tube	2434 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.082
Detector resolution: 8.33 pixels mm^-1	θmax = 27.5°, θmin = 1.3°
ω scans	h = −4→4
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −15→15
Tmin = 0.814, Tmax = 0.981	l = −20→21
12829 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.153	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + 0.6876P] where P = (Fo^2 + 2Fc^2)/3
3372 reflections	(Δ/σ)max < 0.001
201 parameters	Δρmax = 0.34 e Å^−3
0 restraints	Δρmin = −0.39 e Å^−3

Special details

Experimental. The data were 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 (Ų)

	x	y	z	Uiso*/Ueq
Cl1	0.8935 (2)	0.12507 (6)	0.38183 (5)	0.0232 (2)
Cl2	0.4109 (2)	−0.30594 (6)	0.47820 (5)	0.0277 (2)
O1	0.1962 (6)	0.78761 (17)	0.14256 (13)	0.0223 (5)
O2	0.0641 (6)	0.61213 (18)	0.27697 (13)	0.0233 (5)
O3	0.9485 (6)	0.12845 (18)	0.12963 (13)	0.0255 (5)
C1	0.7420 (8)	0.0135 (2)	0.35209 (19)	0.0192 (6)
C2	0.6568 (8)	−0.0890 (3)	0.41734 (19)	0.0212 (6)
H2A	0.6794	−0.0963	0.4733	0.025*
C3	0.5375 (8)	−0.1799 (3)	0.39647 (19)	0.0216 (7)
C4	0.5100 (9)	−0.1727 (3)	0.3137 (2)	0.0234 (7)
H4A	0.4314	−0.2349	0.3010	0.028*
C5	0.6031 (8)	−0.0702 (2)	0.25014 (19)	0.0208 (6)
H5A	0.5919	−0.0649	0.1941	0.025*
C6	0.7134 (8)	0.0259 (2)	0.26787 (18)	0.0189 (6)
C7	0.7834 (8)	0.1358 (2)	0.19392 (19)	0.0199 (6)
C8	0.6301 (8)	0.2445 (3)	0.2018 (2)	0.0207 (6)
H8A	0.4870	0.2422	0.2502	0.025*
C9	0.6895 (8)	0.3475 (3)	0.14110 (19)	0.0212 (7)
H9A	0.8308	0.3461	0.0932	0.025*
C10	0.5577 (8)	0.4603 (2)	0.14220 (18)	0.0183 (6)
C11	0.6317 (8)	0.5572 (3)	0.07113 (19)	0.0208 (6)
H11A	0.7609	0.5476	0.0241	0.025*
C12	0.5172 (8)	0.6678 (2)	0.06890 (18)	0.0203 (6)
H12A	0.5715	0.7312	0.0209	0.024*
C13	0.3229 (8)	0.6836 (2)	0.13787 (19)	0.0188 (6)
C14	0.2487 (8)	0.5864 (2)	0.21155 (18)	0.0187 (6)
C15	0.3607 (8)	0.4773 (2)	0.21246 (18)	0.0194 (6)
H15A	0.3055	0.4137	0.2602	0.023*
C16	0.2727 (9)	0.8863 (3)	0.06898 (19)	0.0235 (7)
H16A	0.1735	0.9550	0.0787	0.035*
H16B	0.1746	0.8766	0.0216	0.035*
H16C	0.5213	0.8934	0.0572	0.035*
C17	−0.0242 (9)	0.5175 (3)	0.35175 (19)	0.0247 (7)
H17A	−0.1650	0.5455	0.3917	0.037*
H17B	0.1856	0.4810	0.3760	0.037*
H17C	−0.1526	0.4622	0.3380	0.037*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0269 (4)	0.0220 (4)	0.0222 (4)	−0.0026 (3)	−0.0012 (3)	−0.0091 (3)
Cl2	0.0317 (5)	0.0199 (4)	0.0254 (4)	−0.0016 (3)	0.0027 (3)	−0.0006 (3)
O1	0.0298 (13)	0.0152 (10)	0.0193 (11)	0.0024 (9)	0.0012 (9)	−0.0036 (8)
O2	0.0294 (12)	0.0190 (10)	0.0202 (11)	−0.0005 (9)	0.0045 (9)	−0.0068 (8)
O3	0.0343 (13)	0.0210 (11)	0.0196 (11)	0.0003 (10)	0.0038 (9)	−0.0067 (9)
C1	0.0190 (15)	0.0174 (13)	0.0222 (15)	0.0013 (11)	0.0001 (12)	−0.0088 (11)
C2	0.0189 (15)	0.0225 (14)	0.0201 (15)	0.0031 (12)	−0.0014 (12)	−0.0051 (12)
C3	0.0180 (16)	0.0183 (14)	0.0238 (16)	0.0033 (12)	0.0022 (12)	−0.0024 (12)
C4	0.0256 (17)	0.0168 (14)	0.0282 (17)	0.0003 (12)	−0.0027 (13)	−0.0080 (12)
C5	0.0249 (17)	0.0187 (14)	0.0192 (15)	0.0009 (12)	−0.0024 (12)	−0.0071 (11)
C6	0.0185 (15)	0.0188 (14)	0.0177 (14)	0.0021 (11)	−0.0007 (11)	−0.0044 (11)
C7	0.0226 (16)	0.0191 (14)	0.0185 (15)	−0.0010 (12)	−0.0021 (12)	−0.0066 (11)
C8	0.0183 (16)	0.0222 (14)	0.0221 (15)	0.0006 (12)	0.0001 (12)	−0.0087 (12)
C9	0.0196 (16)	0.0243 (15)	0.0192 (15)	−0.0031 (12)	−0.0014 (12)	−0.0063 (12)
C10	0.0170 (15)	0.0164 (13)	0.0212 (15)	−0.0003 (11)	−0.0036 (11)	−0.0052 (11)
C11	0.0210 (16)	0.0224 (14)	0.0175 (14)	−0.0028 (12)	0.0006 (11)	−0.0049 (11)
C12	0.0245 (16)	0.0159 (13)	0.0183 (15)	−0.0004 (12)	0.0001 (12)	−0.0034 (11)
C13	0.0209 (16)	0.0150 (13)	0.0220 (15)	0.0028 (11)	−0.0033 (12)	−0.0081 (11)
C14	0.0186 (15)	0.0198 (14)	0.0175 (14)	−0.0012 (12)	0.0016 (11)	−0.0064 (11)
C15	0.0187 (15)	0.0178 (14)	0.0191 (15)	−0.0003 (12)	−0.0017 (12)	−0.0026 (11)
C16	0.0279 (17)	0.0163 (14)	0.0231 (16)	0.0003 (12)	−0.0023 (13)	−0.0025 (12)
C17	0.0270 (17)	0.0252 (15)	0.0198 (15)	−0.0017 (13)	0.0019 (12)	−0.0058 (12)

Geometric parameters (Å, º)

Cl1—C1	1.750 (3)	C8—H8A	0.9300
Cl2—C3	1.744 (3)	C9—C10	1.449 (4)
O1—C13	1.360 (4)	C9—H9A	0.9300
O1—C16	1.431 (3)	C10—C11	1.393 (4)
O2—C14	1.366 (4)	C10—C15	1.408 (4)
O2—C17	1.424 (3)	C11—C12	1.388 (4)
O3—C7	1.226 (4)	C11—H11A	0.9300
C1—C6	1.390 (4)	C12—C13	1.380 (4)
C1—C2	1.393 (4)	C12—H12A	0.9300
C2—C3	1.387 (4)	C13—C14	1.420 (4)
C2—H2A	0.9300	C14—C15	1.374 (4)
C3—C4	1.382 (5)	C15—H15A	0.9300
C4—C5	1.388 (4)	C16—H16A	0.9600
C4—H4A	0.9300	C16—H16B	0.9600
C5—C6	1.403 (4)	C16—H16C	0.9600
C5—H5A	0.9300	C17—H17A	0.9600
C6—C7	1.512 (4)	C17—H17B	0.9600
C7—C8	1.464 (4)	C17—H17C	0.9600
C8—C9	1.345 (4)
C13—O1—C16	115.9 (2)	C11—C10—C9	118.9 (3)
C14—O2—C17	117.0 (2)	C15—C10—C9	123.0 (3)
C6—C1—C2	121.9 (3)	C12—C11—C10	121.6 (3)
C6—C1—Cl1	121.8 (2)	C12—C11—H11A	119.2
C2—C1—Cl1	116.3 (2)	C10—C11—H11A	119.2
C3—C2—C1	118.1 (3)	C13—C12—C11	120.0 (3)
C3—C2—H2A	120.9	C13—C12—H12A	120.0
C1—C2—H2A	120.9	C11—C12—H12A	120.0
C4—C3—C2	122.2 (3)	O1—C13—C12	125.0 (3)
C4—C3—Cl2	119.4 (2)	O1—C13—C14	115.5 (3)
C2—C3—Cl2	118.4 (2)	C12—C13—C14	119.5 (3)
C3—C4—C5	118.1 (3)	O2—C14—C15	125.5 (2)
C3—C4—H4A	120.9	O2—C14—C13	114.7 (3)
C5—C4—H4A	120.9	C15—C14—C13	119.8 (3)
C4—C5—C6	122.0 (3)	C14—C15—C10	121.1 (3)
C4—C5—H5A	119.0	C14—C15—H15A	119.5
C6—C5—H5A	119.0	C10—C15—H15A	119.5
C1—C6—C5	117.5 (2)	O1—C16—H16A	109.5
C1—C6—C7	125.2 (3)	O1—C16—H16B	109.5
C5—C6—C7	117.3 (3)	H16A—C16—H16B	109.5
O3—C7—C8	123.8 (3)	O1—C16—H16C	109.5
O3—C7—C6	118.6 (3)	H16A—C16—H16C	109.5
C8—C7—C6	117.5 (3)	H16B—C16—H16C	109.5
C9—C8—C7	122.1 (3)	O2—C17—H17A	109.5
C9—C8—H8A	119.0	O2—C17—H17B	109.5
C7—C8—H8A	119.0	H17A—C17—H17B	109.5
C8—C9—C10	127.1 (3)	O2—C17—H17C	109.5
C8—C9—H9A	116.4	H17A—C17—H17C	109.5
C10—C9—H9A	116.4	H17B—C17—H17C	109.5
C11—C10—C15	118.1 (3)
C6—C1—C2—C3	−0.6 (5)	C8—C9—C10—C11	−176.4 (3)
Cl1—C1—C2—C3	−179.7 (2)	C8—C9—C10—C15	4.4 (5)
C1—C2—C3—C4	1.8 (5)	C15—C10—C11—C12	0.2 (4)
C1—C2—C3—Cl2	−177.0 (2)	C9—C10—C11—C12	−179.0 (3)
C2—C3—C4—C5	−0.6 (5)	C10—C11—C12—C13	−0.5 (5)
Cl2—C3—C4—C5	178.2 (2)	C16—O1—C13—C12	0.5 (4)
C3—C4—C5—C6	−1.8 (5)	C16—O1—C13—C14	179.3 (3)
C2—C1—C6—C5	−1.6 (5)	C11—C12—C13—O1	−179.7 (3)
Cl1—C1—C6—C5	177.4 (2)	C11—C12—C13—C14	1.5 (4)
C2—C1—C6—C7	176.8 (3)	C17—O2—C14—C15	−1.1 (4)
Cl1—C1—C6—C7	−4.2 (5)	C17—O2—C14—C13	178.6 (3)
C4—C5—C6—C1	2.8 (5)	O1—C13—C14—O2	−0.8 (4)
C4—C5—C6—C7	−175.7 (3)	C12—C13—C14—O2	178.1 (3)
C1—C6—C7—O3	137.2 (3)	O1—C13—C14—C15	178.9 (3)
C5—C6—C7—O3	−44.4 (4)	C12—C13—C14—C15	−2.2 (4)
C1—C6—C7—C8	−46.5 (4)	O2—C14—C15—C10	−178.4 (3)
C5—C6—C7—C8	131.9 (3)	C13—C14—C15—C10	1.9 (4)
O3—C7—C8—C9	−6.9 (5)	C11—C10—C15—C14	−0.9 (4)
C6—C7—C8—C9	177.0 (3)	C9—C10—C15—C14	178.2 (3)
C7—C8—C9—C10	−179.0 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4A···O2^i	0.93	2.57	3.475 (4)	165
C8—H8A···Cl1	0.93	2.78	3.139 (3)	103
C9—H9A···O3	0.93	2.55	2.866 (4)	100

Symmetry code: (i) x, y−1, z.