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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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804018549/wn6272sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804018549/wn6272Isup2.hkl
Contains datablock I

CCDC reference: 251633

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

Computing details top

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 top
Crystal data top
C10H7Cl3OF(000) = 504
Mr = 249.51Dx = 1.512 Mg m3
Orthorhombic, PnmaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2nCell parameters from 1773 reflections
a = 10.4802 (7) Åθ = 2.4–25.0°
b = 7.1166 (10) ŵ = 0.80 mm1
c = 14.69240 (14) ÅT = 298 K
V = 1095.81 (17) Å3Block, colorless
Z = 40.29 × 0.25 × 0.20 mm
Data collection top
Bruker APEX area-detector
diffractometer
1082 independent reflections
Radiation source: fine-focus sealed tube932 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.024
φ and ω scansθmax = 25.3°, θmin = 2.4°
Absorption correction: multi-scan
(SADABS; Bruker, 2002)
h = 1212
Tmin = 0.802, Tmax = 0.857k = 68
5398 measured reflectionsl = 1717
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.079Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.228H atoms treated by a mixture of independent and constrained refinement
S = 1.08 w = 1/[σ2(Fo2) + (0.1112P)2 + 2.0938P]
where P = (Fo2 + 2Fc2)/3
1082 reflections(Δ/σ)max < 0.001
82 parametersΔρmax = 1.10 e Å3
0 restraintsΔρmin = 0.58 e Å3
Special details top

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 (Å2) top
xyzUiso*/Ueq
Cl10.46399 (14)0.0487 (2)0.64530 (10)0.0884 (7)
Cl20.6641 (2)0.25000.73919 (13)0.1431 (16)
O10.7505 (4)0.25000.3870 (3)0.0713 (14)
C11.0119 (7)0.25000.3588 (4)0.0655 (18)
H10.95840.25000.30830.079*
C21.1414 (7)0.25000.3462 (5)0.076 (2)
H21.17520.25000.28770.091*
C31.2207 (7)0.25000.4204 (5)0.073 (2)
H31.30870.25000.41230.088*
C41.1706 (6)0.25000.5065 (5)0.0682 (18)
H41.22510.25000.55650.082*
C51.0414 (6)0.25000.5200 (4)0.0550 (15)
H51.00850.25000.57880.066*
C60.9589 (5)0.25000.4449 (4)0.0458 (13)
C70.8189 (5)0.25000.4538 (4)0.0506 (14)
C80.7606 (6)0.25000.5458 (4)0.0599 (16)
H80.81360.25000.59650.072*
C90.6383 (6)0.25000.5575 (4)0.0547 (15)
H90.58930.25000.50480.066*
C100.5665 (6)0.25000.6442 (4)0.0644 (18)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0707 (10)0.0932 (12)0.1013 (12)0.0041 (7)0.0234 (7)0.0184 (8)
Cl20.0653 (13)0.323 (5)0.0409 (10)0.0000.0046 (8)0.000
O10.051 (2)0.118 (4)0.045 (2)0.0000.007 (2)0.000
C10.061 (4)0.092 (5)0.043 (3)0.0000.003 (3)0.000
C20.061 (4)0.105 (6)0.061 (4)0.0000.021 (3)0.000
C30.048 (3)0.083 (5)0.088 (5)0.0000.011 (4)0.000
C40.050 (4)0.091 (5)0.064 (4)0.0000.009 (3)0.000
C50.052 (3)0.068 (4)0.045 (3)0.0000.001 (3)0.000
C60.048 (3)0.047 (3)0.042 (3)0.0000.001 (2)0.000
C70.049 (3)0.060 (3)0.043 (3)0.0000.002 (2)0.000
C80.043 (3)0.091 (5)0.046 (3)0.0000.003 (2)0.000
C90.052 (3)0.071 (4)0.041 (3)0.0000.003 (3)0.000
C100.046 (3)0.097 (5)0.050 (4)0.0000.002 (3)0.000
Geometric parameters (Å, º) top
Cl1—C101.791 (4)C4—H40.9300
Cl2—C101.730 (6)C5—C61.402 (8)
O1—C71.216 (7)C5—H50.9300
C1—C21.370 (10)C6—C71.473 (8)
C1—C61.382 (8)C7—C81.482 (8)
C1—H10.9300C8—C91.294 (9)
C2—C31.371 (10)C8—H80.9300
C2—H20.9300C9—C101.479 (8)
C3—C41.370 (10)C9—H90.9300
C3—H30.9300C10—Cl1i1.791 (4)
C4—C51.368 (9)
C2—C1—C6121.4 (6)C5—C6—C7123.0 (5)
C2—C1—H1119.3O1—C7—C6121.1 (5)
C6—C1—H1119.3O1—C7—C8119.5 (5)
C1—C2—C3119.6 (6)C6—C7—C8119.4 (5)
C1—C2—H2120.2C9—C8—C7122.0 (6)
C3—C2—H2120.2C9—C8—H8119.0
C4—C3—C2120.1 (6)C7—C8—H8119.0
C4—C3—H3119.9C8—C9—C10128.3 (6)
C2—C3—H3119.9C8—C9—H9115.9
C5—C4—C3120.9 (6)C10—C9—H9115.9
C5—C4—H4119.6C9—C10—Cl2113.2 (5)
C3—C4—H4119.6C9—C10—Cl1i108.2 (3)
C4—C5—C6119.7 (6)Cl2—C10—Cl1i110.3 (2)
C4—C5—H5120.1C9—C10—Cl1108.2 (3)
C6—C5—H5120.1Cl2—C10—Cl1110.3 (2)
C1—C6—C5118.2 (5)Cl1i—C10—Cl1106.3 (4)
C1—C6—C7118.8 (5)
Symmetry code: (i) x, y+1/2, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C9—H9···O10.932.422.767 (7)102
C8—H8···Cl20.932.623.017 (6)107
 

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