1-(2,4-Dichloro-5-fluoro­phen­yl)-3-(3,4-dimethoxy­phen­yl)prop-2-en-1-one

In the title biologically active compound, C₁₇H₁₃Cl₂FO₃, the central C=C double bond is trans configured. The mol­ecule consists of two essentially planar parts which are twisted by 67.06 (2)° with respect to each other.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C)= 0.002 Å
• R factor = 0.030
• wR factor = 0.078
• Data-to-parameter ratio = 13.9

checkCIF/PLATON results

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Computing details

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PLATON.

1-(2,4-Dichloro-5-fluorophenyl)-3-(3,4-dimethoxyphenyl)prop-2-en-1-one

Crystal data

C17H13Cl2FO3	F(000) = 728
Mr = 355.17	Dx = 1.492 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 11877 reflections
a = 6.8572 (5) Å	θ = 3.7–25.8°
b = 16.7211 (11) Å	µ = 0.43 mm^−1
c = 13.9299 (12) Å	T = 173 K
β = 98.173 (6)°	Block, colourless
V = 1581.0 (2) Å^3	0.48 × 0.46 × 0.43 mm
Z = 4

Data collection

Stoe IPDS II two-circle diffractometer	2940 independent reflections
Radiation source: fine-focus sealed tube	2728 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.030
ω scans	θmax = 25.6°, θmin = 3.7°
Absorption correction: multi-scan (MULABS; Spek, 2003; Blessing, 1995)	h = −8→8
Tmin = 0.819, Tmax = 0.836	k = −20→20
11672 measured reflections	l = −16→14

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.030	H-atom parameters constrained
wR(F^2) = 0.078	w = 1/[σ^2(Fo^2) + (0.0405P)^2 + 0.6433P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max = 0.001
2940 reflections	Δρmax = 0.25 e Å^−3
211 parameters	Δρmin = −0.27 e Å^−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0178 (15)

Special details

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
O1	0.6296 (2)	0.77074 (6)	0.28042 (8)	0.0381 (3)
C1	0.6169 (2)	0.69789 (8)	0.27130 (10)	0.0231 (3)
C2	0.6617 (2)	0.64396 (8)	0.35428 (10)	0.0227 (3)
H2	0.6880	0.6671	0.4171	0.027*
C3	0.66825 (19)	0.56360 (8)	0.34741 (10)	0.0209 (3)
H3	0.6387	0.5419	0.2840	0.025*
C11	0.5477 (2)	0.66259 (8)	0.17172 (9)	0.0202 (3)
C12	0.6519 (2)	0.67201 (8)	0.09323 (10)	0.0220 (3)
Cl12	0.87494 (6)	0.72414 (3)	0.10673 (3)	0.03626 (14)
C13	0.5843 (2)	0.64029 (8)	0.00189 (10)	0.0251 (3)
H13	0.6581	0.6469	−0.0504	0.030*
C14	0.4066 (2)	0.59884 (8)	−0.01101 (10)	0.0247 (3)
Cl14	0.31409 (7)	0.55880 (2)	−0.12331 (3)	0.03771 (14)
C15	0.3011 (2)	0.59011 (9)	0.06595 (11)	0.0271 (3)
F15	0.12876 (16)	0.55009 (6)	0.05296 (8)	0.0459 (3)
C16	0.3693 (2)	0.62082 (8)	0.15687 (10)	0.0248 (3)
H16	0.2953	0.6135	0.2089	0.030*
C21	0.71543 (18)	0.50595 (8)	0.42613 (10)	0.0192 (3)
C22	0.76240 (19)	0.52988 (8)	0.52448 (10)	0.0189 (3)
H22	0.7641	0.5851	0.5406	0.023*
C23	0.80558 (18)	0.47377 (8)	0.59676 (10)	0.0184 (3)
C24	0.80408 (18)	0.39091 (8)	0.57349 (10)	0.0189 (3)
C25	0.7561 (2)	0.36685 (8)	0.47734 (10)	0.0218 (3)
H25	0.7527	0.3116	0.4613	0.026*
C26	0.71280 (19)	0.42423 (8)	0.40452 (10)	0.0222 (3)
H26	0.6810	0.4074	0.3390	0.027*
O27	0.85085 (15)	0.49003 (6)	0.69379 (7)	0.0241 (2)
C27	0.8323 (2)	0.57144 (8)	0.72334 (11)	0.0275 (3)
H27A	0.9285	0.6046	0.6959	0.041*
H27B	0.8568	0.5747	0.7943	0.041*
H27C	0.6990	0.5907	0.7001	0.041*
O28	0.84959 (15)	0.34136 (6)	0.65125 (7)	0.0236 (2)
C28	0.8443 (3)	0.25682 (8)	0.63327 (12)	0.0311 (3)
H28A	0.7119	0.2414	0.6030	0.047*
H28B	0.8775	0.2281	0.6947	0.047*
H28C	0.9400	0.2433	0.5898	0.047*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0688 (8)	0.0230 (6)	0.0234 (6)	−0.0100 (5)	0.0094 (5)	−0.0022 (4)
C1	0.0278 (7)	0.0249 (7)	0.0175 (7)	−0.0050 (5)	0.0063 (5)	−0.0012 (5)
C2	0.0255 (7)	0.0281 (7)	0.0143 (6)	−0.0043 (5)	0.0026 (5)	−0.0009 (5)
C3	0.0184 (6)	0.0291 (7)	0.0155 (6)	−0.0011 (5)	0.0033 (5)	−0.0019 (5)
C11	0.0267 (7)	0.0181 (6)	0.0157 (6)	0.0008 (5)	0.0023 (5)	0.0022 (5)
C12	0.0252 (7)	0.0219 (7)	0.0190 (7)	0.0008 (5)	0.0037 (5)	0.0028 (5)
Cl12	0.0319 (2)	0.0480 (3)	0.0309 (2)	−0.01281 (16)	0.01128 (16)	−0.00367 (16)
C13	0.0348 (8)	0.0250 (7)	0.0164 (7)	0.0058 (6)	0.0069 (6)	0.0025 (5)
C14	0.0374 (8)	0.0192 (6)	0.0153 (7)	0.0064 (6)	−0.0042 (6)	−0.0006 (5)
Cl14	0.0590 (3)	0.0301 (2)	0.0196 (2)	0.00643 (17)	−0.00987 (17)	−0.00625 (14)
C15	0.0285 (7)	0.0243 (7)	0.0269 (8)	−0.0038 (6)	−0.0020 (6)	−0.0013 (6)
F15	0.0404 (6)	0.0536 (6)	0.0419 (6)	−0.0224 (5)	−0.0002 (5)	−0.0099 (5)
C16	0.0286 (7)	0.0258 (7)	0.0206 (7)	−0.0032 (6)	0.0059 (6)	0.0010 (6)
C21	0.0149 (6)	0.0253 (7)	0.0178 (6)	−0.0010 (5)	0.0039 (5)	−0.0009 (5)
C22	0.0177 (6)	0.0208 (6)	0.0184 (7)	−0.0012 (5)	0.0034 (5)	−0.0015 (5)
C23	0.0174 (6)	0.0231 (6)	0.0153 (6)	−0.0024 (5)	0.0041 (5)	−0.0030 (5)
C24	0.0169 (6)	0.0212 (6)	0.0193 (7)	−0.0009 (5)	0.0048 (5)	0.0006 (5)
C25	0.0226 (6)	0.0211 (6)	0.0222 (7)	−0.0004 (5)	0.0046 (5)	−0.0052 (5)
C26	0.0215 (6)	0.0277 (7)	0.0173 (7)	0.0000 (5)	0.0029 (5)	−0.0052 (5)
O27	0.0368 (6)	0.0206 (5)	0.0144 (5)	−0.0010 (4)	0.0026 (4)	−0.0022 (4)
C27	0.0378 (8)	0.0228 (7)	0.0213 (7)	−0.0004 (6)	0.0017 (6)	−0.0066 (6)
O28	0.0322 (5)	0.0181 (5)	0.0203 (5)	−0.0010 (4)	0.0033 (4)	−0.0001 (4)
C28	0.0433 (9)	0.0178 (7)	0.0310 (8)	−0.0004 (6)	0.0010 (7)	0.0001 (6)

Geometric parameters (Å, º)

O1—C1	1.2266 (18)	C21—C22	1.4196 (19)
C1—C2	1.4638 (19)	C22—C23	1.3773 (19)
C1—C11	1.5201 (18)	C22—H22	0.9500
C2—C3	1.348 (2)	C23—O27	1.3704 (16)
C2—H2	0.9500	C23—C24	1.4225 (19)
C3—C21	1.4612 (19)	C24—O28	1.3643 (16)
C3—H3	0.9500	C24—C25	1.3924 (19)
C11—C12	1.3975 (19)	C25—C26	1.397 (2)
C11—C16	1.398 (2)	C25—H25	0.9500
C12—C13	1.396 (2)	C26—H26	0.9500
C12—Cl12	1.7471 (14)	O27—C27	1.4329 (16)
C13—C14	1.391 (2)	C27—H27A	0.9800
C13—H13	0.9500	C27—H27B	0.9800
C14—C15	1.384 (2)	C27—H27C	0.9800
C14—Cl14	1.7365 (14)	O28—C28	1.4352 (17)
C15—F15	1.3479 (18)	C28—H28A	0.9800
C15—C16	1.385 (2)	C28—H28B	0.9800
C16—H16	0.9500	C28—H28C	0.9800
C21—C26	1.3988 (19)
O1—C1—C2	121.74 (13)	C23—C22—C21	120.62 (12)
O1—C1—C11	119.24 (13)	C23—C22—H22	119.7
C2—C1—C11	119.00 (12)	C21—C22—H22	119.7
C3—C2—C1	124.28 (13)	O27—C23—C22	125.51 (12)
C3—C2—H2	117.9	O27—C23—C24	114.29 (12)
C1—C2—H2	117.9	C22—C23—C24	120.20 (12)
C2—C3—C21	127.60 (13)	O28—C24—C25	125.76 (12)
C2—C3—H3	116.2	O28—C24—C23	114.65 (11)
C21—C3—H3	116.2	C25—C24—C23	119.59 (12)
C12—C11—C16	118.33 (13)	C24—C25—C26	119.78 (12)
C12—C11—C1	122.81 (12)	C24—C25—H25	120.1
C16—C11—C1	118.83 (12)	C26—C25—H25	120.1
C13—C12—C11	121.99 (13)	C25—C26—C21	121.32 (12)
C13—C12—Cl12	117.39 (11)	C25—C26—H26	119.3
C11—C12—Cl12	120.62 (11)	C21—C26—H26	119.3
C14—C13—C12	118.59 (13)	C23—O27—C27	117.06 (11)
C14—C13—H13	120.7	O27—C27—H27A	109.5
C12—C13—H13	120.7	O27—C27—H27B	109.5
C15—C14—C13	119.82 (13)	H27A—C27—H27B	109.5
C15—C14—Cl14	119.53 (12)	O27—C27—H27C	109.5
C13—C14—Cl14	120.65 (11)	H27A—C27—H27C	109.5
F15—C15—C14	119.56 (13)	H27B—C27—H27C	109.5
F15—C15—C16	118.86 (14)	C24—O28—C28	117.54 (11)
C14—C15—C16	121.58 (13)	O28—C28—H28A	109.5
C15—C16—C11	119.67 (13)	O28—C28—H28B	109.5
C15—C16—H16	120.2	H28A—C28—H28B	109.5
C11—C16—H16	120.2	O28—C28—H28C	109.5
C26—C21—C22	118.50 (12)	H28A—C28—H28C	109.5
C26—C21—C3	119.23 (12)	H28B—C28—H28C	109.5
C22—C21—C3	122.28 (12)
O1—C1—C2—C3	−173.54 (14)	C12—C11—C16—C15	0.0 (2)
C11—C1—C2—C3	8.1 (2)	C1—C11—C16—C15	178.24 (13)
C1—C2—C3—C21	178.68 (13)	C2—C3—C21—C26	179.42 (13)
O1—C1—C11—C12	63.1 (2)	C2—C3—C21—C22	0.0 (2)
C2—C1—C11—C12	−118.54 (15)	C26—C21—C22—C23	0.41 (19)
O1—C1—C11—C16	−115.03 (16)	C3—C21—C22—C23	179.82 (12)
C2—C1—C11—C16	63.35 (18)	C21—C22—C23—O27	−179.32 (12)
C16—C11—C12—C13	−0.8 (2)	C21—C22—C23—C24	0.18 (19)
C1—C11—C12—C13	−178.91 (13)	O27—C23—C24—O28	−0.57 (16)
C16—C11—C12—Cl12	179.59 (10)	C22—C23—C24—O28	179.88 (11)
C1—C11—C12—Cl12	1.47 (19)	O27—C23—C24—C25	178.67 (12)
C11—C12—C13—C14	0.7 (2)	C22—C23—C24—C25	−0.88 (19)
Cl12—C12—C13—C14	−179.69 (10)	O28—C24—C25—C26	−179.87 (12)
C12—C13—C14—C15	0.2 (2)	C23—C24—C25—C26	1.0 (2)
C12—C13—C14—Cl14	179.44 (10)	C24—C25—C26—C21	−0.4 (2)
C13—C14—C15—F15	179.81 (13)	C22—C21—C26—C25	−0.30 (19)
Cl14—C14—C15—F15	0.55 (19)	C3—C21—C26—C25	−179.73 (12)
C13—C14—C15—C16	−0.9 (2)	C22—C23—O27—C27	6.65 (19)
Cl14—C14—C15—C16	179.81 (11)	C24—C23—O27—C27	−172.87 (11)
F15—C15—C16—C11	−179.92 (13)	C25—C24—O28—C28	−1.2 (2)
C14—C15—C16—C11	0.8 (2)	C23—C24—O28—C28	177.96 (12)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16···O27^i	0.95	2.50	3.3067 (17)	143
C16—H16···O28^i	0.95	2.43	3.3072 (17)	154

Symmetry code: (i) −x+1, −y+1, −z+1.