Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802021785/lh6019sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536802021785/lh6019Isup2.hkl |
CCDC reference: 202366
Key indicators
- Single-crystal X-ray study
- T = 213 K
- Mean (C-C) = 0.003 Å
- R factor = 0.078
- wR factor = 0.199
- Data-to-parameter ratio = 15.1
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
The title compound was prepared by photoinduced reactions of 2,3-dichloronaphto-1,4-quinone with an excess of bicyclopropylidene in benzene solution, and was isolated by column chromatography on silica gel. Single crystals suitable for X-ray diffraction study were obtained from slow evaporation of a petroleum ether–ethyl acetate (15:1 v/v) solution.
The H atoms were fixed geometrically and treated as riding on the parent C atoms, with C—H = 0.93–0.97 Å and Uiso(H) = 1.2 Ueq(C).
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT and SADABS; 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).
C16H12Cl2O2 | Z = 2 |
Mr = 307.16 | F(000) = 316 |
Triclinic, P1 | Dx = 1.551 Mg m−3 |
Hall symbol: -P 1 | Melting point: 432(1) K |
a = 7.2430 (1) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 10.0455 (2) Å | Cell parameters from 3828 reflections |
c = 10.0831 (2) Å | θ = 3.1–28.3° |
α = 85.47° | µ = 0.49 mm−1 |
β = 73.306 (1)° | T = 213 K |
γ = 69.401 (1)° | Block, colorless |
V = 657.59 (2) Å3 | 0.50 × 0.46 × 0.40 mm |
Siemens SMART CCD area-detector diffractometer | 2753 independent reflections |
Radiation source: fine-focus sealed tube | 2464 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.066 |
Detector resolution: 8.33 pixels mm-1 | θmax = 27.0°, θmin = 3.1° |
ω scans | h = −8→9 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | k = −12→11 |
Tmin = 0.792, Tmax = 0.828 | l = −12→12 |
3750 measured reflections |
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)] = 0.078 | H-atom parameters constrained |
wR(F2) = 0.199 | w = 1/[σ2(Fo2) + (0.125P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.07 | (Δ/σ)max = 0.001 |
2753 reflections | Δρmax = 0.97 e Å−3 |
182 parameters | Δρmin = −1.22 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: 0.68 (5) |
C16H12Cl2O2 | γ = 69.401 (1)° |
Mr = 307.16 | V = 657.59 (2) Å3 |
Triclinic, P1 | Z = 2 |
a = 7.2430 (1) Å | Mo Kα radiation |
b = 10.0455 (2) Å | µ = 0.49 mm−1 |
c = 10.0831 (2) Å | T = 213 K |
α = 85.47° | 0.50 × 0.46 × 0.40 mm |
β = 73.306 (1)° |
Siemens SMART CCD area-detector diffractometer | 2753 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2464 reflections with I > 2σ(I) |
Tmin = 0.792, Tmax = 0.828 | Rint = 0.066 |
3750 measured reflections |
R[F2 > 2σ(F2)] = 0.078 | 0 restraints |
wR(F2) = 0.199 | H-atom parameters constrained |
S = 1.07 | Δρmax = 0.97 e Å−3 |
2753 reflections | Δρmin = −1.22 e Å−3 |
182 parameters |
Experimental. The data collection covered over a hemisphere of reciprocal space by a combination of three sets of exposures; each set had a different ϕ angle (0, 88 and 180°) for the crystal and each exposure of 30 s covered 0.3° in ω. The crystal-to-detector distance was 5 cm and the detector swing angle was −35°. Crystal decay was monitored by repeating fifty initial frames at the end of data collection and analysing the intensity of duplicate reflections, and was found to be negligible. |
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. |
x | y | z | Uiso*/Ueq | ||
Cl1 | 0.31434 (9) | 0.53664 (6) | 0.65750 (6) | 0.0284 (3) | |
Cl2 | −0.16104 (9) | 0.62238 (6) | 0.71342 (6) | 0.0275 (3) | |
O1 | 0.4263 (3) | 0.7817 (2) | 0.55929 (18) | 0.0274 (5) | |
O2 | −0.3803 (3) | 0.9268 (2) | 0.7387 (2) | 0.0279 (5) | |
C1 | 0.1680 (3) | 0.7113 (2) | 0.7254 (2) | 0.0158 (5) | |
C2 | 0.2534 (3) | 0.8177 (2) | 0.6358 (2) | 0.0170 (5) | |
C3 | 0.1157 (3) | 0.9690 (2) | 0.6523 (2) | 0.0163 (5) | |
C4 | 0.2023 (4) | 1.0760 (3) | 0.6184 (2) | 0.0225 (5) | |
H4 | 0.3443 | 1.0519 | 0.5916 | 0.027* | |
C5 | 0.0775 (5) | 1.2176 (3) | 0.6247 (3) | 0.0275 (6) | |
H5 | 0.1358 | 1.2883 | 0.6039 | 0.033* | |
C6 | −0.1353 (4) | 1.2540 (3) | 0.6622 (3) | 0.0280 (6) | |
H6 | −0.2185 | 1.3489 | 0.6637 | 0.034* | |
C7 | −0.2237 (4) | 1.1492 (3) | 0.6975 (2) | 0.0222 (5) | |
H7 | −0.3658 | 1.1740 | 0.7231 | 0.027* | |
C8 | −0.0991 (3) | 1.0066 (2) | 0.6943 (2) | 0.0159 (5) | |
C9 | −0.1990 (3) | 0.8973 (2) | 0.7288 (2) | 0.0165 (5) | |
C10 | −0.0734 (3) | 0.7485 (2) | 0.7655 (2) | 0.0147 (5) | |
C11 | −0.0781 (3) | 0.7471 (2) | 0.9195 (2) | 0.0159 (5) | |
C12 | 0.1463 (3) | 0.7288 (2) | 0.8804 (2) | 0.0161 (5) | |
C13 | −0.2507 (4) | 0.8345 (3) | 1.0358 (2) | 0.0264 (6) | |
H13A | −0.3788 | 0.8904 | 1.0157 | 0.032* | |
H13B | −0.2157 | 0.8774 | 1.1036 | 0.032* | |
C14 | −0.1908 (4) | 0.6749 (3) | 1.0331 (2) | 0.0251 (6) | |
H14B | −0.1199 | 0.6220 | 1.0993 | 0.030* | |
H14A | −0.2830 | 0.6350 | 1.0114 | 0.030* | |
C15 | 0.2465 (4) | 0.8102 (3) | 0.9380 (3) | 0.0276 (6) | |
H15A | 0.1640 | 0.8720 | 1.0184 | 0.033* | |
H15B | 0.3474 | 0.8439 | 0.8730 | 0.033* | |
C16 | 0.3007 (4) | 0.6517 (3) | 0.9566 (3) | 0.0271 (6) | |
H16B | 0.4344 | 0.5904 | 0.9030 | 0.033* | |
H16A | 0.2511 | 0.6185 | 1.0484 | 0.033* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0235 (4) | 0.0179 (4) | 0.0309 (4) | 0.0011 (3) | 0.0030 (3) | −0.0049 (3) |
Cl2 | 0.0297 (4) | 0.0260 (4) | 0.0334 (5) | −0.0161 (3) | −0.0094 (3) | −0.0035 (3) |
O1 | 0.0144 (8) | 0.0348 (10) | 0.0265 (9) | −0.0061 (7) | 0.0000 (7) | 0.0049 (7) |
O2 | 0.0138 (9) | 0.0327 (10) | 0.0380 (10) | −0.0075 (7) | −0.0110 (7) | 0.0079 (8) |
C1 | 0.0112 (9) | 0.0132 (10) | 0.0181 (10) | 0.0001 (8) | −0.0017 (8) | −0.0012 (8) |
C2 | 0.0131 (10) | 0.0233 (12) | 0.0152 (10) | −0.0056 (9) | −0.0064 (8) | 0.0036 (8) |
C3 | 0.0166 (10) | 0.0201 (11) | 0.0134 (10) | −0.0070 (9) | −0.0062 (8) | 0.0043 (8) |
C4 | 0.0248 (12) | 0.0277 (13) | 0.0203 (11) | −0.0143 (10) | −0.0092 (9) | 0.0061 (9) |
C5 | 0.0411 (15) | 0.0241 (12) | 0.0262 (12) | −0.0193 (11) | −0.0148 (11) | 0.0076 (9) |
C6 | 0.0391 (15) | 0.0151 (11) | 0.0309 (13) | −0.0056 (10) | −0.0170 (11) | 0.0036 (9) |
C7 | 0.0222 (11) | 0.0190 (11) | 0.0237 (12) | −0.0023 (9) | −0.0099 (9) | 0.0014 (9) |
C8 | 0.0166 (10) | 0.0187 (11) | 0.0127 (10) | −0.0051 (9) | −0.0065 (8) | 0.0029 (8) |
C9 | 0.0142 (10) | 0.0203 (11) | 0.0145 (10) | −0.0046 (9) | −0.0052 (8) | 0.0018 (8) |
C10 | 0.0137 (10) | 0.0157 (10) | 0.0158 (10) | −0.0060 (8) | −0.0046 (8) | 0.0004 (8) |
C11 | 0.0152 (10) | 0.0162 (10) | 0.0152 (10) | −0.0045 (8) | −0.0042 (8) | 0.0026 (8) |
C12 | 0.0124 (10) | 0.0179 (11) | 0.0167 (10) | −0.0035 (8) | −0.0048 (8) | 0.0033 (8) |
C13 | 0.0211 (12) | 0.0278 (13) | 0.0197 (11) | 0.0003 (10) | −0.0007 (9) | −0.0007 (9) |
C14 | 0.0232 (12) | 0.0273 (13) | 0.0204 (11) | −0.0091 (10) | −0.0006 (9) | 0.0072 (9) |
C15 | 0.0301 (13) | 0.0341 (14) | 0.0273 (12) | −0.0175 (11) | −0.0147 (10) | 0.0062 (10) |
C16 | 0.0213 (12) | 0.0328 (14) | 0.0266 (12) | −0.0058 (10) | −0.0129 (10) | 0.0111 (10) |
Cl1—C1 | 1.770 (2) | C8—C9 | 1.484 (3) |
Cl2—C10 | 1.773 (2) | C9—C10 | 1.532 (3) |
O1—C2 | 1.210 (3) | C10—C11 | 1.542 (3) |
O2—C9 | 1.216 (3) | C11—C14 | 1.501 (3) |
C1—C2 | 1.528 (3) | C11—C13 | 1.503 (3) |
C1—C12 | 1.543 (3) | C11—C12 | 1.505 (3) |
C1—C10 | 1.587 (3) | C12—C16 | 1.494 (3) |
C2—C3 | 1.487 (3) | C12—C15 | 1.505 (3) |
C3—C4 | 1.399 (3) | C13—C14 | 1.507 (4) |
C3—C8 | 1.406 (3) | C13—H13A | 0.9700 |
C4—C5 | 1.386 (4) | C13—H13B | 0.9700 |
C4—H4 | 0.9300 | C14—H14B | 0.9700 |
C5—C6 | 1.394 (4) | C14—H14A | 0.9700 |
C5—H5 | 0.9300 | C15—C16 | 1.510 (4) |
C6—C7 | 1.389 (4) | C15—H15A | 0.9700 |
C6—H6 | 0.9300 | C15—H15B | 0.9700 |
C7—C8 | 1.396 (3) | C16—H16B | 0.9700 |
C7—H7 | 0.9300 | C16—H16A | 0.9700 |
C2—C1—C12 | 112.53 (17) | C14—C11—C13 | 60.24 (16) |
C2—C1—C10 | 116.73 (17) | C14—C11—C12 | 127.45 (19) |
C12—C1—C10 | 87.88 (15) | C13—C11—C12 | 129.1 (2) |
C2—C1—Cl1 | 109.73 (15) | C14—C11—C10 | 126.07 (19) |
C12—C1—Cl1 | 113.80 (15) | C13—C11—C10 | 126.69 (19) |
C10—C1—Cl1 | 114.76 (15) | C12—C11—C10 | 90.93 (16) |
O1—C2—C3 | 121.7 (2) | C16—C12—C11 | 128.12 (19) |
O1—C2—C1 | 121.9 (2) | C16—C12—C15 | 60.48 (16) |
C3—C2—C1 | 116.33 (18) | C11—C12—C15 | 127.4 (2) |
C4—C3—C8 | 119.4 (2) | C16—C12—C1 | 126.87 (19) |
C4—C3—C2 | 119.0 (2) | C11—C12—C1 | 91.77 (16) |
C8—C3—C2 | 121.48 (19) | C15—C12—C1 | 125.41 (18) |
C5—C4—C3 | 120.3 (2) | C11—C13—C14 | 59.83 (15) |
C5—C4—H4 | 119.8 | C11—C13—H13A | 117.8 |
C3—C4—H4 | 119.8 | C14—C13—H13A | 117.8 |
C4—C5—C6 | 120.1 (2) | C11—C13—H13B | 117.8 |
C4—C5—H5 | 119.9 | C14—C13—H13B | 117.8 |
C6—C5—H5 | 119.9 | H13A—C13—H13B | 114.9 |
C7—C6—C5 | 120.3 (2) | C11—C14—C13 | 59.94 (15) |
C7—C6—H6 | 119.9 | C11—C14—H14B | 117.8 |
C5—C6—H6 | 119.9 | C13—C14—H14B | 117.8 |
C6—C7—C8 | 119.9 (2) | C11—C14—H14A | 117.8 |
C6—C7—H7 | 120.0 | C13—C14—H14A | 117.8 |
C8—C7—H7 | 120.0 | H14B—C14—H14A | 114.9 |
C7—C8—C3 | 119.9 (2) | C12—C15—C16 | 59.38 (15) |
C7—C8—C9 | 118.4 (2) | C12—C15—H15A | 117.8 |
C3—C8—C9 | 121.6 (2) | C16—C15—H15A | 117.8 |
O2—C9—C8 | 121.3 (2) | C12—C15—H15B | 117.8 |
O2—C9—C10 | 120.0 (2) | C16—C15—H15B | 117.8 |
C8—C9—C10 | 118.42 (18) | H15A—C15—H15B | 115.0 |
C9—C10—C11 | 109.66 (16) | C12—C16—C15 | 60.14 (15) |
C9—C10—C1 | 116.29 (17) | C12—C16—H16B | 117.8 |
C11—C10—C1 | 88.75 (15) | C15—C16—H16B | 117.8 |
C9—C10—Cl2 | 108.72 (14) | C12—C16—H16A | 117.8 |
C11—C10—Cl2 | 115.80 (14) | C15—C16—H16A | 117.8 |
C1—C10—Cl2 | 116.46 (14) | H16B—C16—H16A | 114.9 |
C12—C1—C2—O1 | 107.8 (2) | C12—C1—C10—Cl2 | −124.42 (15) |
C10—C1—C2—O1 | −152.7 (2) | Cl1—C1—C10—Cl2 | −9.1 (2) |
Cl1—C1—C2—O1 | −20.0 (3) | C9—C10—C11—C14 | 108.8 (2) |
C12—C1—C2—C3 | −69.6 (2) | C1—C10—C11—C14 | −133.7 (2) |
C10—C1—C2—C3 | 29.9 (3) | Cl2—C10—C11—C14 | −14.7 (3) |
Cl1—C1—C2—C3 | 162.62 (15) | C9—C10—C11—C13 | 31.7 (3) |
O1—C2—C3—C4 | −21.8 (3) | C1—C10—C11—C13 | 149.2 (2) |
C1—C2—C3—C4 | 155.62 (19) | Cl2—C10—C11—C13 | −91.8 (2) |
O1—C2—C3—C8 | 155.0 (2) | C9—C10—C11—C12 | −111.39 (18) |
C1—C2—C3—C8 | −27.6 (3) | C1—C10—C11—C12 | 6.17 (16) |
C8—C3—C4—C5 | −0.8 (3) | Cl2—C10—C11—C12 | 125.15 (15) |
C2—C3—C4—C5 | 176.1 (2) | C14—C11—C12—C16 | −9.3 (4) |
C3—C4—C5—C6 | −1.3 (4) | C13—C11—C12—C16 | 70.1 (3) |
C4—C5—C6—C7 | 1.9 (4) | C10—C11—C12—C16 | −148.3 (2) |
C5—C6—C7—C8 | −0.5 (4) | C14—C11—C12—C15 | −88.5 (3) |
C6—C7—C8—C3 | −1.5 (3) | C13—C11—C12—C15 | −9.0 (4) |
C6—C7—C8—C9 | −178.3 (2) | C10—C11—C12—C15 | 132.6 (2) |
C4—C3—C8—C7 | 2.1 (3) | C14—C11—C12—C1 | 132.6 (2) |
C2—C3—C8—C7 | −174.62 (19) | C13—C11—C12—C1 | −147.9 (2) |
C4—C3—C8—C9 | 178.86 (19) | C10—C11—C12—C1 | −6.35 (16) |
C2—C3—C8—C9 | 2.1 (3) | C2—C1—C12—C16 | −93.0 (3) |
C7—C8—C9—O2 | 11.3 (3) | C10—C1—C12—C16 | 148.9 (2) |
C3—C8—C9—O2 | −165.5 (2) | Cl1—C1—C12—C16 | 32.6 (3) |
C7—C8—C9—C10 | −163.04 (19) | C2—C1—C12—C11 | 124.34 (18) |
C3—C8—C9—C10 | 20.2 (3) | C10—C1—C12—C11 | 6.17 (16) |
O2—C9—C10—C11 | −91.4 (2) | Cl1—C1—C12—C11 | −110.04 (16) |
C8—C9—C10—C11 | 83.0 (2) | C2—C1—C12—C15 | −15.8 (3) |
O2—C9—C10—C1 | 169.9 (2) | C10—C1—C12—C15 | −134.0 (2) |
C8—C9—C10—C1 | −15.7 (3) | Cl1—C1—C12—C15 | 109.8 (2) |
O2—C9—C10—Cl2 | 36.1 (2) | C12—C11—C13—C14 | −116.0 (3) |
C8—C9—C10—Cl2 | −149.46 (16) | C10—C11—C13—C14 | 114.8 (2) |
C2—C1—C10—C9 | −8.9 (3) | C12—C11—C14—C13 | 118.5 (3) |
C12—C1—C10—C9 | 105.36 (18) | C10—C11—C14—C13 | −115.8 (2) |
Cl1—C1—C10—C9 | −139.33 (16) | C11—C12—C15—C16 | 117.4 (3) |
C2—C1—C10—C11 | −120.27 (19) | C1—C12—C15—C16 | −116.3 (2) |
C12—C1—C10—C11 | −6.02 (15) | C11—C12—C16—C15 | −116.3 (3) |
Cl1—C1—C10—C11 | 109.29 (15) | C1—C12—C16—C15 | 114.1 (2) |
C2—C1—C10—Cl2 | 121.34 (17) |
D—H···A | D—H | H···A | D···A | D—H···A |
C15—H15B···O2i | 0.97 | 2.42 | 3.384 (4) | 172 |
Symmetry code: (i) x+1, y, z. |
Experimental details
Crystal data | |
Chemical formula | C16H12Cl2O2 |
Mr | 307.16 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 213 |
a, b, c (Å) | 7.2430 (1), 10.0455 (2), 10.0831 (2) |
α, β, γ (°) | 85.47, 73.306 (1), 69.401 (1) |
V (Å3) | 657.59 (2) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.49 |
Crystal size (mm) | 0.50 × 0.46 × 0.40 |
Data collection | |
Diffractometer | Siemens SMART CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.792, 0.828 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 3750, 2753, 2464 |
Rint | 0.066 |
(sin θ/λ)max (Å−1) | 0.639 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.078, 0.199, 1.07 |
No. of reflections | 2753 |
No. of parameters | 182 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.97, −1.22 |
Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SAINT and SADABS, SHELXTL (Sheldrick, 1997), SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 1990).
D—H···A | D—H | H···A | D···A | D—H···A |
C15—H15B···O2i | 0.97 | 2.42 | 3.384 (4) | 172 |
Symmetry code: (i) x+1, y, z. |
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Photoinduced electron transfer (PET) reactions of electron donor bicyclopropylidene and its derivatives have not been widely investigated. With our continuing studies into the PET reactions of electron rich compounds, we have carried out PET reactions of bicyclopropylidene with several quinones (Wang et al., 2002). In this study, we have isolated the title compound, (I), and undertaken its X-ray crystal structure analyses in order to elucidate its steric configuration and conformation.
The bond lengths and angles in (I) (Fig. 1) are within normal ranges (Allen et al., 1987). Those within the dioxotetrahydrocyclobuta[b]napthalene moiety (O1/O2/C1—C12) agree with the corresponding values in a related structure (Taira et al., 1993), except for the C1—C10 bond length [1.587 (3) Å]. which isslightly longer than the corresponding values in the related structure, mainly due to the repulsions of the lone pair electrons of the two attached chlorine substituents.
In (I), the tetrahydronaphtalene moiety (C1–C10) is not coplanar with the attached tetrahydrobenzene ring, being distorted slightly towards a boat conformation. Atoms C2 and C9 are displaced from the C1/C3/C8/C10 plane by 0.339 (2) and 0.202 (2) Å, respectively, and the dihedral angle between the tetrahydrobenzene and benzene rings is 9.5 (1)°.
The cyclobutane moiety (C1/C10–C12) is slightly out of planarity, with the atoms deviating from its mean plane by ±0.042 (3); the dihedral angle of the C1/C10/C12 and C10/C11/C12 planes is 171.2 (2)°. The cyclobutane mean plane makes a dihedral angle of 78.7 (1)° with the tetrahydrobenzene ring, which is conditioned by the sp3 states of the shared C1 and C10 atoms.
The configurations of the two cyclopropyl rings (C11/C13/C14 and C12/C15/C16) with respect to the cyclobutane is determined by the C13—C11—C12—C15 and C14—C11—C12—C16 torsion angles [both are 9.2 (2)°], implying that atoms C11 and C12 are eclipsed. The Cl1—C1—C10—Cl2 torsion angle is 9.1 (2)°, also indicating an eclipsed configuration around atoms C1 and C10. The two cyclopropyl rings are orthogonal to the cyclobutane ring, with dihedral angles of 89.4 (2) and 89.5 (2)°. In the crystal, molecules are linked into extended chains by weak intermolecular C—H···O hydrogen bonds, via unit-cell translations in the a direction (see Fig. 2 and Table 2).