3,4-Dichloro­hypnone

The title compound [systematic name: 1-(3,4-dichloro­phenyl)­ethanone], C₈H₆Cl₂O, was prepared by the reaction of aluminium trichloride with o-dichloro­benzene and acetyl chloride. There is π stacking in the structure.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C)= 0.002 Å
• R factor = 0.033
• wR factor = 0.094
• Data-to-parameter ratio = 16.2

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S1. Comment

Hypnone derivate is an important kind of intermediate in industry of fine chemicals. They are extensively used as starting material in the synthetic of pesticide and medication (Hatanaka et al., 1989). Because of the low melt point of them, the crysstal of hypnone derivate are rare. As part of our search for new hypnone derivate compounds we synthesized the title compound (I), and describe its structure here.

The distance of C7—O1 of 1.201 (2) Å is shorter than the C—O distance of 1.215 Å reported by Haisa et al. (1976). The C4—Cl2 and C3—Cl1 distances of 1.7063 (17) and 1.7072 (17) Å, respectively, are similar to the C—Cl distance of 1.747Å reported by Evans et al. (1988).

Related literature

For related literature, see: Evans & Trotter (1988); Haisa et al. (1976); Hatanaka et al. (1989).

S2. Experimental

A mixture of the o-dichloro benzene (0.1 mol), acetyl chloride (0.1 mol) and aluminium trichloride (0.15 mol), was stirred in refluxing trichloromethane (30 ml) for 5 h to afford the title compound (0.085 mol, yield 85%). Single crystals of the title compound (I) suitable for X-ray measurements were obtained by recrystallization from EtOH at room temperature.

S3. Refinement

H atoms were fixed geometrically and allowed to ride on their attached atoms, with C—H = 0.93 - 0.96 Å, and U_iso=1.2–1.5U_eq.

Computing details

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); 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, 1997); software used to prepare material for publication: SHELXTL.

Figures

Fig. 1. The structure of the title compound (I), showing 30% probability displacement ellipsoids and the atom-numbering scheme.

1-(3,4-dichlorophenyl)ethanone

Crystal data

C8H6Cl2O	F(000) = 384
Mr = 189.03	Dx = 1.571 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3035 reflections
a = 7.2878 (15) Å	θ = 2.9–26.4°
b = 10.597 (2) Å	µ = 0.74 mm^−1
c = 10.610 (2) Å	T = 294 K
β = 102.717 (3)°	Block, colourless
V = 799.3 (3) Å^3	0.20 × 0.18 × 0.16 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer	1637 independent reflections
Radiation source: fine-focus sealed tube	1449 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.018
φ and ω scans	θmax = 26.4°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −9→8
Tmin = 0.866, Tmax = 0.890	k = −9→13
4489 measured reflections	l = −13→12

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.094	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0506P)^2 + 0.2513P] where P = (Fo^2 + 2Fc^2)/3
1637 reflections	(Δ/σ)max = 0.001
101 parameters	Δρmax = 0.26 e Å^−3
0 restraints	Δρmin = −0.29 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	0.09028 (8)	0.22661 (5)	0.39055 (6)	0.06076 (19)
Cl2	0.12712 (9)	0.44153 (5)	0.19719 (5)	0.0671 (2)
O1	0.4462 (2)	0.73876 (15)	0.70133 (14)	0.0665 (4)
C1	0.2990 (2)	0.50645 (18)	0.61880 (17)	0.0466 (4)
H1	0.3372	0.5199	0.7073	0.056*
C2	0.2314 (3)	0.39160 (18)	0.57462 (18)	0.0495 (4)
H2	0.2227	0.3271	0.6325	0.059*
C3	0.1763 (2)	0.37135 (16)	0.44448 (18)	0.0421 (4)
C4	0.1904 (2)	0.46613 (16)	0.35993 (16)	0.0409 (4)
C5	0.2580 (2)	0.58170 (16)	0.40441 (16)	0.0409 (4)
H5	0.2675	0.6458	0.3464	0.049*
C6	0.3120 (2)	0.60317 (16)	0.53495 (16)	0.0383 (4)
C7	0.3855 (2)	0.72665 (17)	0.58718 (18)	0.0462 (4)
C8	0.3836 (4)	0.83410 (19)	0.4994 (2)	0.0637 (5)
H8A	0.4336	0.9073	0.5485	0.096*
H8B	0.2567	0.8507	0.4540	0.096*
H8C	0.4592	0.8146	0.4385	0.096*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0682 (3)	0.0402 (3)	0.0742 (4)	−0.0130 (2)	0.0164 (3)	−0.0048 (2)
Cl2	0.1019 (4)	0.0493 (3)	0.0420 (3)	−0.0029 (2)	−0.0015 (2)	−0.00618 (19)
O1	0.0833 (10)	0.0658 (10)	0.0479 (8)	−0.0126 (8)	0.0089 (7)	−0.0161 (7)
C1	0.0508 (9)	0.0526 (10)	0.0374 (8)	−0.0012 (8)	0.0117 (7)	0.0003 (7)
C2	0.0566 (10)	0.0464 (10)	0.0486 (10)	−0.0027 (8)	0.0182 (8)	0.0091 (8)
C3	0.0387 (8)	0.0353 (8)	0.0540 (10)	−0.0018 (6)	0.0138 (7)	−0.0021 (7)
C4	0.0432 (8)	0.0399 (9)	0.0385 (8)	0.0028 (7)	0.0065 (7)	−0.0021 (7)
C5	0.0460 (9)	0.0363 (8)	0.0403 (9)	0.0011 (7)	0.0095 (7)	0.0014 (7)
C6	0.0362 (8)	0.0406 (9)	0.0398 (8)	0.0017 (6)	0.0122 (6)	−0.0022 (7)
C7	0.0469 (9)	0.0463 (10)	0.0471 (10)	−0.0023 (7)	0.0139 (8)	−0.0109 (8)
C8	0.0870 (15)	0.0401 (10)	0.0653 (13)	−0.0095 (10)	0.0195 (11)	−0.0077 (9)

Geometric parameters (Å, º)

Cl1—C3	1.7072 (17)	C4—C5	1.365 (2)
Cl2—C4	1.7063 (17)	C5—C6	1.373 (2)
O1—C7	1.201 (2)	C5—H5	0.9300
C1—C2	1.357 (3)	C6—C7	1.475 (2)
C1—C6	1.374 (3)	C7—C8	1.469 (3)
C1—H1	0.9300	C8—H8A	0.9600
C2—C3	1.367 (3)	C8—H8B	0.9600
C2—H2	0.9300	C8—H8C	0.9600
C3—C4	1.366 (2)
C2—C1—C6	121.12 (17)	C6—C5—H5	120.0
C2—C1—H1	119.4	C5—C6—C1	118.97 (16)
C6—C1—H1	119.4	C5—C6—C7	121.72 (16)
C1—C2—C3	119.55 (17)	C1—C6—C7	119.31 (15)
C1—C2—H2	120.2	O1—C7—C8	120.41 (18)
C3—C2—H2	120.2	O1—C7—C6	119.75 (17)
C4—C3—C2	120.00 (16)	C8—C7—C6	119.84 (16)
C4—C3—Cl1	121.05 (14)	C7—C8—H8A	109.5
C2—C3—Cl1	118.95 (14)	C7—C8—H8B	109.5
C5—C4—C3	120.43 (16)	H8A—C8—H8B	109.5
C5—C4—Cl2	118.92 (14)	C7—C8—H8C	109.5
C3—C4—Cl2	120.65 (14)	H8A—C8—H8C	109.5
C4—C5—C6	119.93 (16)	H8B—C8—H8C	109.5
C4—C5—H5	120.0
C6—C1—C2—C3	0.4 (3)	C4—C5—C6—C1	0.9 (2)
C1—C2—C3—C4	0.4 (3)	C4—C5—C6—C7	−179.87 (15)
C1—C2—C3—Cl1	−179.62 (14)	C2—C1—C6—C5	−1.0 (3)
C2—C3—C4—C5	−0.5 (3)	C2—C1—C6—C7	179.71 (16)
Cl1—C3—C4—C5	179.49 (13)	C5—C6—C7—O1	−173.66 (17)
C2—C3—C4—Cl2	178.55 (14)	C1—C6—C7—O1	5.6 (3)
Cl1—C3—C4—Cl2	−1.4 (2)	C5—C6—C7—C8	6.5 (3)
C3—C4—C5—C6	−0.1 (3)	C1—C6—C7—C8	−174.27 (18)
Cl2—C4—C5—C6	−179.19 (12)