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The non-planar title mol­ecule, C15H10Cl2O, contains two benzene rings linked by a –CH=CH—C(=O)– bridge. In the crystal structure, the mol­ecules are paired through π–π inter­actions and the pairs are connected to each other via hydrogen-bonding inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805024566/tk6238sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805024566/tk6238Isup2.hkl
Contains datablock I

CCDC reference: 283995

Key indicators

  • Single-crystal X-ray study
  • T = 193 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.048
  • wR factor = 0.105
  • Data-to-parameter ratio = 15.5

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT480_ALERT_4_C Long H...A H-Bond Reported H2 .. O1 .. 2.81 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H14 .. O1 .. 2.81 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H12 .. O1 .. 2.84 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H9 .. CL1 .. 3.02 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 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 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 4 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: CrystalClear (Rigaku, 1999); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

1,3-Bis(4-chlorophenyl)prop-2-en-1-one top
Crystal data top
C15H10Cl2OF(000) = 568
Mr = 277.13Dx = 1.468 Mg m3
Monoclinic, P21/cMelting point = 428–430 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71070 Å
a = 15.325 (3) ÅCell parameters from 4017 reflections
b = 14.009 (2) Åθ = 3.0–26.4°
c = 5.8501 (10) ŵ = 0.50 mm1
β = 92.908 (4)°T = 193 K
V = 1254.3 (4) Å3Block, colourless
Z = 40.25 × 0.23 × 0.10 mm
Data collection top
Rigaku Mercury
diffractometer
2549 independent reflections
Radiation source: fine-focus sealed tube2109 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.037
ω and φ scansθmax = 26.4°, θmin = 3.0°
Absorption correction: multi-scan
(ABSCOR; Jacobson, 1998)
h = 1919
Tmin = 0.885, Tmax = 0.952k = 1716
12957 measured reflectionsl = 77
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)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.105H-atom parameters constrained
S = 1.15 w = 1/[σ2(Fo2) + (0.0351P)2 + 0.6039P]
where P = (Fo2 + 2Fc2)/3
2549 reflections(Δ/σ)max = 0.001
164 parametersΔρmax = 0.25 e Å3
0 restraintsΔρmin = 0.27 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
Cl10.13688 (4)0.87551 (5)0.24181 (12)0.0520 (2)
Cl20.98538 (4)0.85574 (5)0.76034 (11)0.0515 (2)
O10.52958 (11)0.87320 (13)0.1987 (3)0.0462 (4)
C10.41966 (14)0.87436 (14)0.0693 (4)0.0293 (5)
C20.39509 (14)0.90720 (15)0.2824 (4)0.0325 (5)
H20.43850.92770.39340.039*
C30.30778 (15)0.90992 (15)0.3322 (4)0.0351 (5)
H30.29080.93410.47510.042*
C40.24574 (14)0.87724 (15)0.1726 (4)0.0332 (5)
C50.26815 (14)0.84412 (15)0.0390 (4)0.0344 (5)
H50.22450.82220.14770.041*
C60.35493 (14)0.84341 (14)0.0895 (4)0.0321 (5)
H60.37100.82140.23520.039*
C70.74095 (13)0.88928 (14)0.3031 (3)0.0283 (5)
C80.82155 (14)0.92138 (15)0.2331 (4)0.0334 (5)
H80.82470.95030.08680.040*
C90.89706 (15)0.91220 (16)0.3713 (4)0.0370 (5)
H90.95140.93450.32110.044*
C100.89194 (14)0.87001 (15)0.5835 (4)0.0336 (5)
C110.81306 (14)0.83811 (15)0.6594 (4)0.0331 (5)
H110.81060.80930.80600.040*
C120.73804 (14)0.84827 (14)0.5214 (4)0.0306 (5)
H120.68370.82730.57460.037*
C130.51247 (14)0.87384 (15)0.0047 (4)0.0332 (5)
C140.58259 (14)0.87272 (15)0.1879 (4)0.0326 (5)
H140.56880.85560.33910.039*
C150.66429 (14)0.89506 (14)0.1455 (4)0.0308 (5)
H150.67400.91730.00450.037*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0340 (3)0.0621 (4)0.0605 (4)0.0071 (3)0.0075 (3)0.0001 (3)
Cl20.0373 (3)0.0677 (4)0.0482 (4)0.0036 (3)0.0093 (3)0.0080 (3)
O10.0388 (9)0.0693 (12)0.0307 (9)0.0046 (8)0.0035 (7)0.0001 (8)
C10.0326 (11)0.0260 (10)0.0291 (10)0.0005 (9)0.0000 (9)0.0035 (8)
C20.0377 (12)0.0313 (11)0.0281 (11)0.0014 (9)0.0032 (9)0.0006 (9)
C30.0439 (13)0.0316 (11)0.0299 (11)0.0062 (10)0.0037 (10)0.0001 (9)
C40.0307 (11)0.0291 (11)0.0400 (12)0.0046 (9)0.0022 (10)0.0038 (9)
C50.0345 (12)0.0325 (11)0.0354 (12)0.0003 (9)0.0051 (10)0.0023 (9)
C60.0382 (12)0.0303 (11)0.0276 (11)0.0009 (9)0.0007 (9)0.0015 (9)
C70.0322 (11)0.0245 (10)0.0286 (10)0.0026 (8)0.0038 (9)0.0003 (8)
C80.0379 (12)0.0320 (11)0.0307 (11)0.0025 (10)0.0059 (10)0.0025 (9)
C90.0341 (12)0.0400 (13)0.0373 (12)0.0054 (10)0.0057 (10)0.0025 (10)
C100.0321 (11)0.0354 (12)0.0328 (11)0.0008 (9)0.0018 (9)0.0023 (9)
C110.0379 (12)0.0326 (11)0.0288 (11)0.0006 (9)0.0014 (9)0.0002 (9)
C120.0314 (11)0.0293 (11)0.0314 (11)0.0014 (9)0.0055 (9)0.0000 (9)
C130.0364 (12)0.0309 (11)0.0320 (11)0.0026 (9)0.0013 (10)0.0017 (9)
C140.0337 (12)0.0373 (12)0.0266 (11)0.0010 (9)0.0007 (9)0.0043 (9)
C150.0355 (12)0.0279 (10)0.0292 (11)0.0026 (9)0.0029 (9)0.0022 (9)
Geometric parameters (Å, º) top
Cl1—C41.737 (2)C7—C121.403 (3)
Cl2—C101.735 (2)C7—C151.458 (3)
O1—C131.231 (3)C8—C91.384 (3)
C1—C61.394 (3)C8—H80.9500
C1—C21.398 (3)C9—C101.381 (3)
C1—C131.490 (3)C9—H90.9500
C2—C31.384 (3)C10—C111.383 (3)
C2—H20.9500C11—C121.378 (3)
C3—C41.377 (3)C11—H110.9500
C3—H30.9500C12—H120.9500
C4—C51.382 (3)C13—C141.479 (3)
C5—C61.377 (3)C14—C151.326 (3)
C5—H50.9500C14—H140.9500
C6—H60.9500C15—H150.9500
C7—C81.395 (3)
C6—C1—C2118.8 (2)C7—C8—H8119.2
C6—C1—C13119.05 (19)C10—C9—C8118.8 (2)
C2—C1—C13122.11 (19)C10—C9—H9120.6
C3—C2—C1120.3 (2)C8—C9—H9120.6
C3—C2—H2119.9C9—C10—C11121.2 (2)
C1—C2—H2119.9C9—C10—Cl2120.17 (17)
C4—C3—C2119.31 (19)C11—C10—Cl2118.67 (17)
C4—C3—H3120.3C12—C11—C10119.7 (2)
C2—C3—H3120.3C12—C11—H11120.2
C3—C4—C5121.7 (2)C10—C11—H11120.2
C3—C4—Cl1119.00 (17)C11—C12—C7120.76 (19)
C5—C4—Cl1119.31 (17)C11—C12—H12119.6
C6—C5—C4118.8 (2)C7—C12—H12119.6
C6—C5—H5120.6O1—C13—C14121.2 (2)
C4—C5—H5120.6O1—C13—C1119.9 (2)
C5—C6—C1121.15 (19)C14—C13—C1118.95 (18)
C5—C6—H6119.4C15—C14—C13121.34 (19)
C1—C6—H6119.4C15—C14—H14119.3
C8—C7—C12117.96 (19)C13—C14—H14119.3
C8—C7—C15119.53 (18)C14—C15—C7127.33 (19)
C12—C7—C15122.44 (19)C14—C15—H15116.3
C9—C8—C7121.66 (19)C7—C15—H15116.3
C9—C8—H8119.2
C6—C1—C2—C30.9 (3)C9—C10—C11—C120.1 (3)
C13—C1—C2—C3177.48 (19)Cl2—C10—C11—C12179.68 (16)
C1—C2—C3—C42.0 (3)C10—C11—C12—C71.0 (3)
C2—C3—C4—C51.8 (3)C8—C7—C12—C111.5 (3)
C2—C3—C4—Cl1176.91 (16)C15—C7—C12—C11175.48 (19)
C3—C4—C5—C60.5 (3)C6—C1—C13—O120.7 (3)
Cl1—C4—C5—C6178.24 (16)C2—C1—C13—O1157.7 (2)
C4—C5—C6—C10.7 (3)C6—C1—C13—C14158.45 (19)
C2—C1—C6—C50.5 (3)C2—C1—C13—C1423.2 (3)
C13—C1—C6—C5178.89 (19)O1—C13—C14—C1517.3 (3)
C12—C7—C8—C91.0 (3)C1—C13—C14—C15163.6 (2)
C15—C7—C8—C9176.1 (2)C13—C14—C15—C7174.3 (2)
C7—C8—C9—C100.1 (3)C8—C7—C15—C14176.1 (2)
C8—C9—C10—C110.7 (3)C12—C7—C15—C146.9 (3)
C8—C9—C10—Cl2179.14 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2···O1i0.952.813.613 (3)143
C14—H14···O1i0.952.813.719 (3)160
C12—H12···O1i0.952.843.680 (3)148
C9—H9···Cl1ii0.953.023.825 (2)144
Symmetry codes: (i) x, y, z+1; (ii) x+1, y, z.
 

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