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In the title compound, C18H8Cl4O2, a crystallographic twofold rotation axis passes through the centroid of the cyclo­butane ring. The indanone moieties are each planar and each forms a dihedral angle of 66.68 (8)° with the cyclo­butane ring. O1...Cl1 short contacts link symmetry-related mol­ecules into chains along the c axis.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803025236/ci6300sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803025236/ci6300Isup2.hkl
Contains datablock I

CCDC reference: 227884

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.029
  • wR factor = 0.084
  • Data-to-parameter ratio = 15.7

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low ....... 0.99
Alert level C PLAT431_ALERT_2_C Short Inter HL..A Contact Cl1 .. O1 = 3.18 Ang.
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 1 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 1 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 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 1990).

4 b,4c,9a,9c-Tetrachloro-4 b,4c,9 b,9c-tetrahydroindeno[1',2':3,4] cyclobuta[1,2-a]indene-5,10-dione top
Crystal data top
C18H8Cl4O2F(000) = 800
Mr = 398.04Dx = 1.634 Mg m3
Monoclinic, C2/cMelting point: 533–534 K K
Hall symbol: -C 2ycMo Kα radiation, λ = 0.71073 Å
a = 15.8948 (10) ÅCell parameters from 3658 reflections
b = 8.7186 (5) Åθ = 2.8–28.3°
c = 13.5633 (9) ŵ = 0.74 mm1
β = 120.563 (1)°T = 293 K
V = 1618.47 (17) Å3Block, colourless
Z = 40.52 × 0.38 × 0.26 mm
Data collection top
Siemens SMART CCD area-detector
diffractometer
1972 independent reflections
Radiation source: fine-focus sealed tube1773 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.016
Detector resolution: 8.33 pixels mm-1θmax = 28.3°, θmin = 2.8°
ω scansh = 1921
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
k = 1011
Tmin = 0.700, Tmax = 0.831l = 1712
4882 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.029All H-atom parameters refined
wR(F2) = 0.085 w = 1/[σ2(Fo2) + (0.0468P)2 + 0.9124P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max < 0.001
1972 reflectionsΔρmax = 0.31 e Å3
126 parametersΔρmin = 0.22 e Å3
0 restraintsExtinction correction: SHELXTL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0106 (9)
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
Cl10.40907 (3)0.56400 (4)0.04477 (3)0.04009 (14)
Cl20.37269 (3)0.61081 (5)0.25740 (3)0.04610 (15)
O10.33305 (10)0.27874 (18)0.30264 (11)0.0589 (4)
C10.37101 (10)0.29964 (19)0.24605 (13)0.0371 (3)
C20.37187 (10)0.19876 (17)0.15985 (13)0.0365 (3)
C30.33201 (13)0.0518 (2)0.12840 (17)0.0491 (4)
C40.33980 (14)0.0223 (2)0.0438 (2)0.0572 (5)
C50.38544 (14)0.0469 (2)0.00877 (19)0.0546 (5)
C60.42619 (12)0.1923 (2)0.02289 (15)0.0437 (4)
C70.41892 (10)0.26789 (16)0.10835 (12)0.0325 (3)
C80.45550 (10)0.42702 (15)0.15581 (12)0.0294 (3)
C90.43113 (10)0.44237 (16)0.25358 (12)0.0309 (3)
H30.3005 (18)0.005 (3)0.165 (2)0.064 (6)*
H40.3119 (18)0.118 (3)0.021 (2)0.070 (7)*
H50.3872 (18)0.010 (3)0.071 (2)0.070 (7)*
H60.4565 (14)0.238 (2)0.0136 (17)0.049 (5)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0372 (2)0.0433 (2)0.0372 (2)0.00569 (14)0.01705 (16)0.01113 (14)
Cl20.0435 (2)0.0513 (3)0.0424 (2)0.01613 (16)0.02103 (18)0.00348 (16)
O10.0567 (8)0.0812 (10)0.0542 (8)0.0276 (7)0.0395 (7)0.0148 (7)
C10.0283 (7)0.0487 (9)0.0334 (7)0.0074 (6)0.0151 (6)0.0024 (6)
C20.0295 (7)0.0394 (8)0.0371 (7)0.0041 (5)0.0144 (6)0.0018 (6)
C30.0419 (9)0.0439 (9)0.0578 (11)0.0111 (7)0.0226 (8)0.0035 (7)
C40.0463 (10)0.0408 (9)0.0760 (14)0.0086 (7)0.0250 (9)0.0171 (9)
C50.0465 (10)0.0538 (10)0.0615 (12)0.0013 (8)0.0259 (9)0.0231 (9)
C60.0415 (8)0.0487 (9)0.0442 (9)0.0006 (7)0.0243 (7)0.0085 (7)
C70.0271 (6)0.0342 (7)0.0327 (7)0.0008 (5)0.0128 (5)0.0016 (5)
C80.0281 (6)0.0323 (6)0.0285 (6)0.0015 (5)0.0149 (5)0.0021 (5)
C90.0280 (6)0.0350 (7)0.0309 (7)0.0008 (5)0.0159 (5)0.0020 (5)
Geometric parameters (Å, º) top
Cl1—C81.7632 (14)C4—H40.92 (3)
Cl2—C91.7524 (14)C5—C61.388 (3)
O1—C11.2072 (18)C5—H51.00 (3)
C1—C21.469 (2)C6—C71.388 (2)
C1—C91.540 (2)C6—H60.94 (2)
C2—C71.394 (2)C7—C81.5155 (19)
C2—C31.397 (2)C8—C91.5648 (19)
C3—C41.376 (3)C8—C9i1.5885 (19)
C3—H30.96 (2)C9—C8i1.5885 (19)
C4—C51.387 (3)
O1—C1—C2128.73 (15)C7—C6—H6121.3 (13)
O1—C1—C9125.00 (15)C6—C7—C2120.45 (14)
C2—C1—C9106.26 (11)C6—C7—C8127.78 (14)
C7—C2—C3121.29 (15)C2—C7—C8111.76 (12)
C7—C2—C1111.39 (13)C7—C8—C9103.38 (11)
C3—C2—C1127.32 (15)C7—C8—C9i116.42 (11)
C4—C3—C2117.79 (18)C9—C8—C9i90.54 (10)
C4—C3—H3121.9 (15)C7—C8—Cl1110.71 (10)
C2—C3—H3120.3 (15)C9—C8—Cl1119.31 (10)
C3—C4—C5121.11 (17)C9i—C8—Cl1114.91 (9)
C3—C4—H4118.3 (15)C1—C9—C8106.70 (11)
C5—C4—H4120.5 (15)C1—C9—C8i113.88 (11)
C4—C5—C6121.45 (18)C8—C9—C8i88.63 (10)
C4—C5—H5118.0 (14)C1—C9—Cl2111.02 (10)
C6—C5—H5120.6 (14)C8—C9—Cl2117.39 (10)
C5—C6—C7117.90 (17)C8i—C9—Cl2117.23 (10)
C5—C6—H6120.8 (13)
O1—C1—C2—C7176.51 (17)C2—C7—C8—C9i101.83 (14)
C9—C1—C2—C74.43 (17)C6—C7—C8—Cl154.27 (18)
O1—C1—C2—C33.2 (3)C2—C7—C8—Cl1124.49 (11)
C9—C1—C2—C3175.85 (16)O1—C1—C9—C8173.92 (16)
C7—C2—C3—C40.7 (3)C2—C1—C9—C86.97 (15)
C1—C2—C3—C4179.04 (17)O1—C1—C9—C8i90.02 (19)
C2—C3—C4—C50.2 (3)C2—C1—C9—C8i89.08 (14)
C3—C4—C5—C60.9 (3)O1—C1—C9—Cl244.9 (2)
C4—C5—C6—C70.8 (3)C2—C1—C9—Cl2136.00 (11)
C5—C6—C7—C20.1 (2)C7—C8—C9—C16.81 (14)
C5—C6—C7—C8178.75 (15)C9i—C8—C9—C1124.18 (10)
C3—C2—C7—C60.8 (2)Cl1—C8—C9—C1116.58 (11)
C1—C2—C7—C6178.93 (14)C7—C8—C9—C8i107.74 (9)
C3—C2—C7—C8179.68 (14)C9i—C8—C9—C8i9.63 (14)
C1—C2—C7—C80.07 (17)Cl1—C8—C9—C8i128.86 (8)
C6—C7—C8—C9176.83 (15)C7—C8—C9—Cl2132.06 (10)
C2—C7—C8—C94.41 (15)C9i—C8—C9—Cl2110.57 (8)
C6—C7—C8—C9i79.41 (19)Cl1—C8—C9—Cl28.66 (15)
Symmetry code: (i) x+1, y, z+1/2.
 

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