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In the title compound, C
18H
8Cl
4O
2, 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
CCDC reference: 227884
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (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
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
C18H8Cl4O2 | F(000) = 800 |
Mr = 398.04 | Dx = 1.634 Mg m−3 |
Monoclinic, C2/c | Melting point: 533–534 K K |
Hall symbol: -C 2yc | Mo Kα radiation, λ = 0.71073 Å |
a = 15.8948 (10) Å | Cell parameters from 3658 reflections |
b = 8.7186 (5) Å | θ = 2.8–28.3° |
c = 13.5633 (9) Å | µ = 0.74 mm−1 |
β = 120.563 (1)° | T = 293 K |
V = 1618.47 (17) Å3 | Block, colourless |
Z = 4 | 0.52 × 0.38 × 0.26 mm |
Data collection top
Siemens SMART CCD area-detector diffractometer | 1972 independent reflections |
Radiation source: fine-focus sealed tube | 1773 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.016 |
Detector resolution: 8.33 pixels mm-1 | θmax = 28.3°, θmin = 2.8° |
ω scans | h = −19→21 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | k = −10→11 |
Tmin = 0.700, Tmax = 0.831 | l = −17→12 |
4882 measured reflections | |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.029 | All 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 reflections | Δρmax = 0.31 e Å−3 |
126 parameters | Δρmin = −0.22 e Å−3 |
0 restraints | Extinction correction: SHELXTL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction 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 | x | y | z | Uiso*/Ueq | |
Cl1 | 0.40907 (3) | 0.56400 (4) | 0.04477 (3) | 0.04009 (14) | |
Cl2 | 0.37269 (3) | 0.61081 (5) | 0.25740 (3) | 0.04610 (15) | |
O1 | 0.33305 (10) | 0.27874 (18) | 0.30264 (11) | 0.0589 (4) | |
C1 | 0.37101 (10) | 0.29964 (19) | 0.24605 (13) | 0.0371 (3) | |
C2 | 0.37187 (10) | 0.19876 (17) | 0.15985 (13) | 0.0365 (3) | |
C3 | 0.33201 (13) | 0.0518 (2) | 0.12840 (17) | 0.0491 (4) | |
C4 | 0.33980 (14) | −0.0223 (2) | 0.0438 (2) | 0.0572 (5) | |
C5 | 0.38544 (14) | 0.0469 (2) | −0.00877 (19) | 0.0546 (5) | |
C6 | 0.42619 (12) | 0.1923 (2) | 0.02289 (15) | 0.0437 (4) | |
C7 | 0.41892 (10) | 0.26789 (16) | 0.10835 (12) | 0.0325 (3) | |
C8 | 0.45550 (10) | 0.42702 (15) | 0.15581 (12) | 0.0294 (3) | |
C9 | 0.43113 (10) | 0.44237 (16) | 0.25358 (12) | 0.0309 (3) | |
H3 | 0.3005 (18) | 0.005 (3) | 0.165 (2) | 0.064 (6)* | |
H4 | 0.3119 (18) | −0.118 (3) | 0.021 (2) | 0.070 (7)* | |
H5 | 0.3872 (18) | −0.010 (3) | −0.071 (2) | 0.070 (7)* | |
H6 | 0.4565 (14) | 0.238 (2) | −0.0136 (17) | 0.049 (5)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.0372 (2) | 0.0433 (2) | 0.0372 (2) | 0.00569 (14) | 0.01705 (16) | 0.01113 (14) |
Cl2 | 0.0435 (2) | 0.0513 (3) | 0.0424 (2) | 0.01613 (16) | 0.02103 (18) | −0.00348 (16) |
O1 | 0.0567 (8) | 0.0812 (10) | 0.0542 (8) | −0.0276 (7) | 0.0395 (7) | −0.0148 (7) |
C1 | 0.0283 (7) | 0.0487 (9) | 0.0334 (7) | −0.0074 (6) | 0.0151 (6) | −0.0024 (6) |
C2 | 0.0295 (7) | 0.0394 (8) | 0.0371 (7) | −0.0041 (5) | 0.0144 (6) | −0.0018 (6) |
C3 | 0.0419 (9) | 0.0439 (9) | 0.0578 (11) | −0.0111 (7) | 0.0226 (8) | −0.0035 (7) |
C4 | 0.0463 (10) | 0.0408 (9) | 0.0760 (14) | −0.0086 (7) | 0.0250 (9) | −0.0171 (9) |
C5 | 0.0465 (10) | 0.0538 (10) | 0.0615 (12) | −0.0013 (8) | 0.0259 (9) | −0.0231 (9) |
C6 | 0.0415 (8) | 0.0487 (9) | 0.0442 (9) | −0.0006 (7) | 0.0243 (7) | −0.0085 (7) |
C7 | 0.0271 (6) | 0.0342 (7) | 0.0327 (7) | 0.0008 (5) | 0.0128 (5) | −0.0016 (5) |
C8 | 0.0281 (6) | 0.0323 (6) | 0.0285 (6) | 0.0015 (5) | 0.0149 (5) | 0.0021 (5) |
C9 | 0.0280 (6) | 0.0350 (7) | 0.0309 (7) | 0.0008 (5) | 0.0159 (5) | −0.0020 (5) |
Geometric parameters (Å, º) top
Cl1—C8 | 1.7632 (14) | C4—H4 | 0.92 (3) |
Cl2—C9 | 1.7524 (14) | C5—C6 | 1.388 (3) |
O1—C1 | 1.2072 (18) | C5—H5 | 1.00 (3) |
C1—C2 | 1.469 (2) | C6—C7 | 1.388 (2) |
C1—C9 | 1.540 (2) | C6—H6 | 0.94 (2) |
C2—C7 | 1.394 (2) | C7—C8 | 1.5155 (19) |
C2—C3 | 1.397 (2) | C8—C9 | 1.5648 (19) |
C3—C4 | 1.376 (3) | C8—C9i | 1.5885 (19) |
C3—H3 | 0.96 (2) | C9—C8i | 1.5885 (19) |
C4—C5 | 1.387 (3) | | |
| | | |
O1—C1—C2 | 128.73 (15) | C7—C6—H6 | 121.3 (13) |
O1—C1—C9 | 125.00 (15) | C6—C7—C2 | 120.45 (14) |
C2—C1—C9 | 106.26 (11) | C6—C7—C8 | 127.78 (14) |
C7—C2—C3 | 121.29 (15) | C2—C7—C8 | 111.76 (12) |
C7—C2—C1 | 111.39 (13) | C7—C8—C9 | 103.38 (11) |
C3—C2—C1 | 127.32 (15) | C7—C8—C9i | 116.42 (11) |
C4—C3—C2 | 117.79 (18) | C9—C8—C9i | 90.54 (10) |
C4—C3—H3 | 121.9 (15) | C7—C8—Cl1 | 110.71 (10) |
C2—C3—H3 | 120.3 (15) | C9—C8—Cl1 | 119.31 (10) |
C3—C4—C5 | 121.11 (17) | C9i—C8—Cl1 | 114.91 (9) |
C3—C4—H4 | 118.3 (15) | C1—C9—C8 | 106.70 (11) |
C5—C4—H4 | 120.5 (15) | C1—C9—C8i | 113.88 (11) |
C4—C5—C6 | 121.45 (18) | C8—C9—C8i | 88.63 (10) |
C4—C5—H5 | 118.0 (14) | C1—C9—Cl2 | 111.02 (10) |
C6—C5—H5 | 120.6 (14) | C8—C9—Cl2 | 117.39 (10) |
C5—C6—C7 | 117.90 (17) | C8i—C9—Cl2 | 117.23 (10) |
C5—C6—H6 | 120.8 (13) | | |
| | | |
O1—C1—C2—C7 | 176.51 (17) | C2—C7—C8—C9i | 101.83 (14) |
C9—C1—C2—C7 | −4.43 (17) | C6—C7—C8—Cl1 | 54.27 (18) |
O1—C1—C2—C3 | −3.2 (3) | C2—C7—C8—Cl1 | −124.49 (11) |
C9—C1—C2—C3 | 175.85 (16) | O1—C1—C9—C8 | −173.92 (16) |
C7—C2—C3—C4 | −0.7 (3) | C2—C1—C9—C8 | 6.97 (15) |
C1—C2—C3—C4 | 179.04 (17) | O1—C1—C9—C8i | 90.02 (19) |
C2—C3—C4—C5 | −0.2 (3) | C2—C1—C9—C8i | −89.08 (14) |
C3—C4—C5—C6 | 0.9 (3) | O1—C1—C9—Cl2 | −44.9 (2) |
C4—C5—C6—C7 | −0.8 (3) | C2—C1—C9—Cl2 | 136.00 (11) |
C5—C6—C7—C2 | −0.1 (2) | C7—C8—C9—C1 | −6.81 (14) |
C5—C6—C7—C8 | −178.75 (15) | C9i—C8—C9—C1 | −124.18 (10) |
C3—C2—C7—C6 | 0.8 (2) | Cl1—C8—C9—C1 | 116.58 (11) |
C1—C2—C7—C6 | −178.93 (14) | C7—C8—C9—C8i | 107.74 (9) |
C3—C2—C7—C8 | 179.68 (14) | C9i—C8—C9—C8i | −9.63 (14) |
C1—C2—C7—C8 | −0.07 (17) | Cl1—C8—C9—C8i | −128.86 (8) |
C6—C7—C8—C9 | −176.83 (15) | C7—C8—C9—Cl2 | −132.06 (10) |
C2—C7—C8—C9 | 4.41 (15) | C9i—C8—C9—Cl2 | 110.57 (8) |
C6—C7—C8—C9i | −79.41 (19) | Cl1—C8—C9—Cl2 | −8.66 (15) |
Symmetry code: (i) −x+1, y, −z+1/2. |
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