2,2′,4′-Trichloro­acetophenone

π–π Stacking inter­actions are present in the crystal structure of the title compound, C₈H₅Cl₃O [systematic name: chloro­methyl 2,4-dichloro­phenyl ketone].

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C)= 0.004 Å
• R factor = 0.054
• wR factor = 0.116
• Data-to-parameter ratio = 14.7

checkCIF/PLATON results

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Computing details

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2002); software used to prepare material for publication: SHELXL97.

Chloromethyl 2,4-dichlorophenyl ketone

Crystal data

C8H5Cl3O	F(000) = 448
Mr = 223.47	Dx = 1.675 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1236 reflections
a = 4.6665 (5) Å	θ = 2.2–25.0°
b = 10.5576 (11) Å	µ = 0.98 mm^−1
c = 17.9978 (18) Å	T = 298 K
β = 92.299 (2)°	Block, colourless
V = 885.98 (16) Å^3	0.31 × 0.17 × 0.16 mm
Z = 4

Data collection

Bruker APEX area-detector diffractometer	1597 independent reflections
Radiation source: fine-focus sealed tube	1415 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.022
φ and ω scans	θmax = 25.2°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −5→4
Tmin = 0.752, Tmax = 0.860	k = −12→11
4613 measured reflections	l = −21→21

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.116	H-atom parameters constrained
S = 1.15	w = 1/[σ^2(Fo^2) + (0.0398P)^2 + 0.8207P] where P = (Fo^2 + 2Fc^2)/3
1597 reflections	(Δ/σ)max < 0.001
109 parameters	Δρmax = 0.28 e Å^−3
0 restraints	Δρmin = −0.26 e Å^−3

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
Cl1	1.2174 (2)	0.85232 (10)	0.00834 (5)	0.0656 (3)
Cl2	0.6176 (3)	0.46122 (8)	0.10169 (6)	0.0778 (4)
Cl3	0.1063 (2)	0.65621 (10)	0.35376 (6)	0.0683 (3)
O1	0.2971 (8)	0.5397 (3)	0.22393 (17)	0.0945 (11)
C1	0.9783 (7)	0.7925 (3)	0.07060 (17)	0.0449 (8)
C2	0.8933 (7)	0.6690 (3)	0.06405 (19)	0.0514 (9)
H2	0.9602	0.6187	0.0260	0.062*
C3	0.7073 (7)	0.6195 (3)	0.11425 (18)	0.0452 (8)
C4	0.6023 (7)	0.6927 (3)	0.17168 (16)	0.0395 (7)
C5	0.6939 (7)	0.8184 (3)	0.17520 (18)	0.0485 (8)
H5	0.6263	0.8703	0.2124	0.058*
C6	0.8806 (7)	0.8686 (3)	0.12572 (18)	0.0497 (8)
H6	0.9392	0.9526	0.1297	0.060*
C7	0.4039 (7)	0.6433 (3)	0.22746 (18)	0.0465 (8)
C8	0.3382 (7)	0.7288 (3)	0.29125 (19)	0.0498 (8)
H8A	0.2498	0.8060	0.2720	0.060*
H8B	0.5158	0.7518	0.3177	0.060*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0575 (6)	0.0798 (7)	0.0613 (6)	0.0006 (5)	0.0232 (4)	0.0155 (5)
Cl2	0.1141 (9)	0.0374 (5)	0.0842 (8)	−0.0056 (5)	0.0346 (6)	−0.0122 (5)
Cl3	0.0714 (6)	0.0650 (6)	0.0712 (7)	0.0108 (5)	0.0362 (5)	0.0166 (5)
O1	0.145 (3)	0.0601 (18)	0.083 (2)	−0.0447 (19)	0.058 (2)	−0.0163 (15)
C1	0.0400 (17)	0.053 (2)	0.0424 (18)	0.0031 (15)	0.0070 (14)	0.0083 (15)
C2	0.058 (2)	0.048 (2)	0.049 (2)	0.0094 (17)	0.0150 (16)	−0.0016 (16)
C3	0.052 (2)	0.0349 (16)	0.0487 (19)	0.0050 (14)	0.0029 (15)	−0.0005 (14)
C4	0.0434 (17)	0.0375 (17)	0.0377 (17)	0.0009 (14)	0.0013 (13)	0.0018 (13)
C5	0.058 (2)	0.0442 (19)	0.0438 (18)	−0.0060 (16)	0.0135 (16)	−0.0066 (14)
C6	0.056 (2)	0.0425 (18)	0.051 (2)	−0.0082 (16)	0.0107 (16)	0.0003 (15)
C7	0.055 (2)	0.0404 (18)	0.0448 (18)	−0.0013 (16)	0.0057 (15)	0.0051 (15)
C8	0.0499 (19)	0.0460 (19)	0.055 (2)	0.0034 (16)	0.0177 (16)	0.0038 (16)

Geometric parameters (Å, º)

Cl1—C1	1.732 (3)	C4—C5	1.395 (4)
Cl2—C3	1.736 (3)	C4—C7	1.487 (4)
Cl3—C8	1.767 (3)	C5—C6	1.376 (4)
O1—C7	1.203 (4)	C5—H5	0.9300
C1—C2	1.367 (5)	C6—H6	0.9300
C1—C6	1.369 (5)	C7—C8	1.502 (5)
C2—C3	1.380 (5)	C8—H8A	0.9700
C2—H2	0.9300	C8—H8B	0.9700
C3—C4	1.395 (4)
C2—C1—C6	121.2 (3)	C4—C5—H5	118.7
C2—C1—Cl1	119.0 (3)	C1—C6—C5	118.8 (3)
C6—C1—Cl1	119.8 (3)	C1—C6—H6	120.6
C1—C2—C3	119.5 (3)	C5—C6—H6	120.6
C1—C2—H2	120.2	O1—C7—C4	123.4 (3)
C3—C2—H2	120.2	O1—C7—C8	119.4 (3)
C2—C3—C4	121.6 (3)	C4—C7—C8	117.2 (3)
C2—C3—Cl2	115.7 (2)	C7—C8—Cl3	112.0 (2)
C4—C3—Cl2	122.7 (3)	C7—C8—H8A	109.2
C3—C4—C5	116.4 (3)	Cl3—C8—H8A	109.2
C3—C4—C7	123.6 (3)	C7—C8—H8B	109.2
C5—C4—C7	120.1 (3)	Cl3—C8—H8B	109.2
C6—C5—C4	122.5 (3)	H8A—C8—H8B	107.9
C6—C5—H5	118.7
C6—C1—C2—C3	−0.6 (5)	C2—C1—C6—C5	0.2 (5)
Cl1—C1—C2—C3	178.7 (3)	Cl1—C1—C6—C5	−179.1 (3)
C1—C2—C3—C4	0.2 (5)	C4—C5—C6—C1	0.5 (5)
C1—C2—C3—Cl2	−179.0 (3)	C3—C4—C7—O1	−6.9 (6)
C2—C3—C4—C5	0.4 (5)	C5—C4—C7—O1	173.3 (4)
Cl2—C3—C4—C5	179.7 (3)	C3—C4—C7—C8	172.8 (3)
C2—C3—C4—C7	−179.4 (3)	C5—C4—C7—C8	−7.1 (5)
Cl2—C3—C4—C7	−0.2 (5)	O1—C7—C8—Cl3	0.9 (5)
C3—C4—C5—C6	−0.8 (5)	C4—C7—C8—Cl3	−178.8 (2)
C7—C4—C5—C6	179.0 (3)