(E)-4,4,4-Tri­chloro-1-phenyl­but-2-en-1-one

In the crystal structure of the title compound, C₁₀H₇Cl₃O, the carbonyl group is in an s-cis conformation and the configuration of the C=C double bond is E. With the exception of two Cl atoms, all the atoms lie on a crystallographic mirror plane. Intramolecular C—H...O and C—H...Cl hydrogen bonds are present.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.009 Å
• R factor = 0.079
• wR factor = 0.228
• Data-to-parameter ratio = 13.2

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT242_ALERT_2_B Check Low    U(eq) as Compared to Neighbors  for        C10

Alert level C
PLAT143_ALERT_4_C su on c - Axis Small or Missing (x 100000) .....         14 Ang.
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          9
PLAT431_ALERT_2_C Short Inter HL..A Contact  Cl1    ..  O1      ..       3.13 Ang.

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

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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: XP in SHELXTL (Bruker, 2002); software used to prepare material for publication: SHELXTL.

(E)-4,4,4-Trichloro-1-phenylbut-2-en-1-one

Crystal data

C10H7Cl3O	F(000) = 504
Mr = 249.51	Dx = 1.512 Mg m^−3
Orthorhombic, Pnma	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2n	Cell parameters from 1773 reflections
a = 10.4802 (7) Å	θ = 2.4–25.0°
b = 7.1166 (10) Å	µ = 0.80 mm^−1
c = 14.69240 (14) Å	T = 298 K
V = 1095.81 (17) Å^3	Block, colorless
Z = 4	0.29 × 0.25 × 0.20 mm

Data collection

Bruker APEX area-detector diffractometer	1082 independent reflections
Radiation source: fine-focus sealed tube	932 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.024
φ and ω scans	θmax = 25.3°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −12→12
Tmin = 0.802, Tmax = 0.857	k = −6→8
5398 measured reflections	l = −17→17

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)] = 0.079	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.228	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ^2(Fo^2) + (0.1112P)^2 + 2.0938P] where P = (Fo^2 + 2Fc^2)/3
1082 reflections	(Δ/σ)max < 0.001
82 parameters	Δρmax = 1.10 e Å^−3
0 restraints	Δρmin = −0.58 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	0.46399 (14)	0.0487 (2)	0.64530 (10)	0.0884 (7)
Cl2	0.6641 (2)	0.2500	0.73919 (13)	0.1431 (16)
O1	0.7505 (4)	0.2500	0.3870 (3)	0.0713 (14)
C1	1.0119 (7)	0.2500	0.3588 (4)	0.0655 (18)
H1	0.9584	0.2500	0.3083	0.079*
C2	1.1414 (7)	0.2500	0.3462 (5)	0.076 (2)
H2	1.1752	0.2500	0.2877	0.091*
C3	1.2207 (7)	0.2500	0.4204 (5)	0.073 (2)
H3	1.3087	0.2500	0.4123	0.088*
C4	1.1706 (6)	0.2500	0.5065 (5)	0.0682 (18)
H4	1.2251	0.2500	0.5565	0.082*
C5	1.0414 (6)	0.2500	0.5200 (4)	0.0550 (15)
H5	1.0085	0.2500	0.5788	0.066*
C6	0.9589 (5)	0.2500	0.4449 (4)	0.0458 (13)
C7	0.8189 (5)	0.2500	0.4538 (4)	0.0506 (14)
C8	0.7606 (6)	0.2500	0.5458 (4)	0.0599 (16)
H8	0.8136	0.2500	0.5965	0.072*
C9	0.6383 (6)	0.2500	0.5575 (4)	0.0547 (15)
H9	0.5893	0.2500	0.5048	0.066*
C10	0.5665 (6)	0.2500	0.6442 (4)	0.0644 (18)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0707 (10)	0.0932 (12)	0.1013 (12)	−0.0041 (7)	0.0234 (7)	0.0184 (8)
Cl2	0.0653 (13)	0.323 (5)	0.0409 (10)	0.000	−0.0046 (8)	0.000
O1	0.051 (2)	0.118 (4)	0.045 (2)	0.000	−0.007 (2)	0.000
C1	0.061 (4)	0.092 (5)	0.043 (3)	0.000	0.003 (3)	0.000
C2	0.061 (4)	0.105 (6)	0.061 (4)	0.000	0.021 (3)	0.000
C3	0.048 (3)	0.083 (5)	0.088 (5)	0.000	0.011 (4)	0.000
C4	0.050 (4)	0.091 (5)	0.064 (4)	0.000	−0.009 (3)	0.000
C5	0.052 (3)	0.068 (4)	0.045 (3)	0.000	0.001 (3)	0.000
C6	0.048 (3)	0.047 (3)	0.042 (3)	0.000	0.001 (2)	0.000
C7	0.049 (3)	0.060 (3)	0.043 (3)	0.000	0.002 (2)	0.000
C8	0.043 (3)	0.091 (5)	0.046 (3)	0.000	−0.003 (2)	0.000
C9	0.052 (3)	0.071 (4)	0.041 (3)	0.000	−0.003 (3)	0.000
C10	0.046 (3)	0.097 (5)	0.050 (4)	0.000	−0.002 (3)	0.000

Geometric parameters (Å, º)

Cl1—C10	1.791 (4)	C4—H4	0.9300
Cl2—C10	1.730 (6)	C5—C6	1.402 (8)
O1—C7	1.216 (7)	C5—H5	0.9300
C1—C2	1.370 (10)	C6—C7	1.473 (8)
C1—C6	1.382 (8)	C7—C8	1.482 (8)
C1—H1	0.9300	C8—C9	1.294 (9)
C2—C3	1.371 (10)	C8—H8	0.9300
C2—H2	0.9300	C9—C10	1.479 (8)
C3—C4	1.370 (10)	C9—H9	0.9300
C3—H3	0.9300	C10—Cl1^i	1.791 (4)
C4—C5	1.368 (9)
C2—C1—C6	121.4 (6)	C5—C6—C7	123.0 (5)
C2—C1—H1	119.3	O1—C7—C6	121.1 (5)
C6—C1—H1	119.3	O1—C7—C8	119.5 (5)
C1—C2—C3	119.6 (6)	C6—C7—C8	119.4 (5)
C1—C2—H2	120.2	C9—C8—C7	122.0 (6)
C3—C2—H2	120.2	C9—C8—H8	119.0
C4—C3—C2	120.1 (6)	C7—C8—H8	119.0
C4—C3—H3	119.9	C8—C9—C10	128.3 (6)
C2—C3—H3	119.9	C8—C9—H9	115.9
C5—C4—C3	120.9 (6)	C10—C9—H9	115.9
C5—C4—H4	119.6	C9—C10—Cl2	113.2 (5)
C3—C4—H4	119.6	C9—C10—Cl1^i	108.2 (3)
C4—C5—C6	119.7 (6)	Cl2—C10—Cl1^i	110.3 (2)
C4—C5—H5	120.1	C9—C10—Cl1	108.2 (3)
C6—C5—H5	120.1	Cl2—C10—Cl1	110.3 (2)
C1—C6—C5	118.2 (5)	Cl1^i—C10—Cl1	106.3 (4)
C1—C6—C7	118.8 (5)

Symmetry code: (i) x, −y+1/2, z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···O1	0.93	2.42	2.767 (7)	102
C8—H8···Cl2	0.93	2.62	3.017 (6)	107