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The title compound [systematic name: 5,6,11,12-tetrahydro-5,11-bis(bromoacetyl)-5,12[1′,2′]:6,11[1′′,2′′]dibenzenodibenzo[
a,
e]cyclooctene], C
32H
22Br
2O
2, is a [4+4] photodimer of 9-(bromoacetyl)anthracene. The molecule is centrosymmetric and contains a long C
sp3—C
sp3 bond of 1.619 (3) Å. Intermolecular C—H
O interactions are observed.
Supporting information
CCDC reference: 647189
Key indicators
- Single-crystal X-ray study
- T = 153 K
- Mean (C-C)= 0.003 Å
- R factor = 0.036
- wR factor = 0.074
- Data-to-parameter ratio = 16.9
checkCIF/PLATON results
No syntax errors found
No errors found in this datablock
Data collection: CrystalClear (Rigaku, 1999); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku/MSC, 2006); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and Mercury (Version 1.3; Bruno et
al., 2002); software used to prepare material for publication: CrystalStructure.
5,6,11,12-Tetrahydro-5,11-bis(bromoacetyl)-
5,12[1',2']:6,11[1'',2'']dibenzenodibenzo[a,e]cyclooctene
top
Crystal data top
C32H22Br2O2 | Z = 1 |
Mr = 598.33 | F(000) = 300.00 |
Triclinic, P1 | Dx = 1.634 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71070 Å |
a = 7.9044 (18) Å | Cell parameters from 1862 reflections |
b = 9.1861 (17) Å | θ = 3.2–27.5° |
c = 9.4138 (17) Å | µ = 3.37 mm−1 |
α = 66.648 (9)° | T = 153 K |
β = 75.696 (10)° | Prism, colorless |
γ = 83.656 (11)° | 0.18 × 0.08 × 0.07 mm |
V = 608.0 (2) Å3 | |
Data collection top
Rigaku Saturn diffractometer | 2444 reflections with I > 2σ(I) |
Detector resolution: 7.31 pixels mm-1 | Rint = 0.033 |
ω scans | θmax = 27.5° |
Absorption correction: multi-scan (REQAB; Jacobson, 1998) | h = −10→10 |
Tmin = 0.634, Tmax = 0.790 | k = −11→11 |
7481 measured reflections | l = −12→12 |
2777 independent reflections | |
Refinement top
Refinement on F2 | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.036 | w = 1/[σ2(Fo2) + (0.0139P)2 + 0.9661P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.074 | (Δ/σ)max = 0.001 |
S = 1.05 | Δρmax = 0.56 e Å−3 |
2777 reflections | Δρmin = −0.48 e Å−3 |
164 parameters | |
Special details top
Refinement. Refinement was performed using all reflections. The weighted R-factor
(wR) and goodness of fit (S) are based on F2.
R-factor (gt) are based on F. The threshold expression of
F2 > 2.0 σ(F2) is used only for calculating R-factor
(gt). |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Br1 | −0.15503 (4) | 0.23664 (4) | 1.28769 (4) | 0.03637 (10) | |
O1 | 0.2409 (2) | 0.2646 (2) | 1.2136 (2) | 0.0388 (5) | |
C1 | 0.3060 (3) | 0.3224 (3) | 0.7982 (2) | 0.0225 (5) | |
C2 | 0.3275 (3) | 0.3776 (3) | 0.6345 (3) | 0.0276 (5) | |
C3 | 0.3903 (3) | 0.2757 (3) | 0.5566 (3) | 0.0300 (6) | |
C4 | 0.4355 (3) | 0.1212 (3) | 0.6417 (3) | 0.0260 (5) | |
C5 | 0.4153 (3) | 0.0643 (2) | 0.8050 (2) | 0.0199 (4) | |
C6 | 0.4760 (3) | −0.0996 (2) | 0.8997 (2) | 0.0197 (4) | |
C7 | 0.3398 (3) | −0.1702 (2) | 1.0506 (2) | 0.0201 (4) | |
C8 | 0.2903 (3) | −0.3277 (3) | 1.1108 (3) | 0.0239 (5) | |
C9 | 0.1686 (3) | −0.3896 (3) | 1.2541 (3) | 0.0289 (5) | |
C10 | 0.0999 (3) | −0.2944 (3) | 1.3380 (3) | 0.0297 (5) | |
C11 | 0.1507 (3) | −0.1379 (3) | 1.2795 (2) | 0.0237 (5) | |
C12 | 0.2678 (3) | −0.0729 (2) | 1.1345 (2) | 0.0192 (4) | |
C13 | 0.3340 (3) | 0.0967 (2) | 1.0652 (2) | 0.0189 (4) | |
C14 | 0.3455 (3) | 0.1649 (2) | 0.8854 (2) | 0.0197 (4) | |
C15 | 0.2017 (3) | 0.1972 (3) | 1.1409 (2) | 0.0232 (5) | |
C16 | 0.0177 (3) | 0.2089 (3) | 1.1143 (3) | 0.0297 (5) | |
H1 | 0.2640 | 0.3926 | 0.8513 | 0.027* | |
H2 | 0.2992 | 0.4846 | 0.5762 | 0.033* | |
H3 | 0.4023 | 0.3120 | 0.4451 | 0.036* | |
H4 | 0.4813 | 0.0528 | 0.5872 | 0.031* | |
H5 | 0.4855 | −0.1667 | 0.8363 | 0.024* | |
H6 | 0.3397 | −0.3934 | 1.0540 | 0.029* | |
H7 | 0.1328 | −0.4965 | 1.2939 | 0.035* | |
H8 | 0.0176 | −0.3366 | 1.4362 | 0.036* | |
H9 | 0.1048 | −0.0744 | 1.3394 | 0.028* | |
H10 | −0.0076 | 0.1112 | 1.1032 | 0.036* | |
H11 | 0.0101 | 0.2996 | 1.0143 | 0.036* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Br1 | 0.02759 (15) | 0.0497 (2) | 0.03578 (17) | 0.00043 (12) | 0.00087 (11) | −0.02542 (14) |
O1 | 0.0315 (10) | 0.0480 (12) | 0.0566 (13) | 0.0100 (9) | −0.0117 (9) | −0.0420 (11) |
C1 | 0.0229 (11) | 0.0225 (12) | 0.0235 (12) | −0.0008 (9) | −0.0043 (9) | −0.0106 (10) |
C2 | 0.0251 (12) | 0.0284 (14) | 0.0243 (13) | −0.0009 (10) | −0.0077 (10) | −0.0036 (11) |
C3 | 0.0293 (13) | 0.0439 (17) | 0.0172 (12) | −0.0010 (11) | −0.0086 (10) | −0.0098 (12) |
C4 | 0.0262 (12) | 0.0355 (15) | 0.0227 (12) | −0.0008 (10) | −0.0059 (10) | −0.0174 (11) |
C5 | 0.0173 (10) | 0.0242 (12) | 0.0215 (11) | −0.0021 (9) | −0.0038 (8) | −0.0121 (10) |
C6 | 0.0214 (11) | 0.0206 (12) | 0.0216 (11) | −0.0004 (9) | −0.0042 (9) | −0.0131 (10) |
C7 | 0.0190 (11) | 0.0198 (12) | 0.0232 (12) | −0.0004 (9) | −0.0054 (9) | −0.0094 (10) |
C8 | 0.0253 (12) | 0.0209 (12) | 0.0300 (13) | −0.0001 (9) | −0.0111 (10) | −0.0115 (11) |
C9 | 0.0313 (13) | 0.0219 (13) | 0.0310 (14) | −0.0061 (10) | −0.0115 (11) | −0.0035 (11) |
C10 | 0.0274 (13) | 0.0328 (15) | 0.0235 (13) | −0.0082 (11) | −0.0036 (10) | −0.0047 (11) |
C11 | 0.0217 (11) | 0.0265 (13) | 0.0231 (12) | −0.0012 (9) | −0.0052 (9) | −0.0095 (10) |
C12 | 0.0183 (10) | 0.0196 (11) | 0.0218 (11) | −0.0006 (8) | −0.0051 (9) | −0.0097 (9) |
C13 | 0.0205 (11) | 0.0196 (12) | 0.0183 (11) | 0.0015 (9) | −0.0030 (8) | −0.0101 (9) |
C14 | 0.0177 (10) | 0.0239 (12) | 0.0199 (11) | −0.0019 (9) | −0.0034 (8) | −0.0109 (10) |
C15 | 0.0262 (12) | 0.0223 (12) | 0.0205 (11) | 0.0054 (9) | −0.0031 (9) | −0.0106 (10) |
C16 | 0.0294 (13) | 0.0402 (16) | 0.0252 (13) | 0.0120 (11) | −0.0072 (10) | −0.0209 (12) |
Geometric parameters (Å, º) top
Br1—C16 | 1.935 (2) | C11—C12 | 1.389 (3) |
O1—C15 | 1.197 (4) | C12—C13 | 1.527 (3) |
C1—C2 | 1.391 (3) | C13—C14 | 1.537 (3) |
C1—C14 | 1.396 (3) | C13—C15 | 1.547 (3) |
C2—C3 | 1.386 (4) | C15—C16 | 1.521 (4) |
C3—C4 | 1.382 (3) | C1—H1 | 0.950 |
C4—C5 | 1.387 (3) | C2—H2 | 0.950 |
C5—C6 | 1.510 (3) | C3—H3 | 0.950 |
C5—C14 | 1.402 (4) | C4—H4 | 0.950 |
C6—C7 | 1.506 (2) | C6—H5 | 1.000 |
C6—C13i | 1.619 (3) | C8—H6 | 0.950 |
C7—C8 | 1.391 (3) | C9—H7 | 0.950 |
C7—C12 | 1.404 (4) | C10—H8 | 0.950 |
C8—C9 | 1.393 (3) | C11—H9 | 0.950 |
C9—C10 | 1.383 (4) | C16—H10 | 0.990 |
C10—C11 | 1.387 (4) | C16—H11 | 0.990 |
| | | |
O1···C8ii | 3.517 (3) | H2···H8x | 2.883 |
O1···C9ii | 3.318 (4) | H2···H8iv | 3.025 |
C2···C2iii | 3.512 (3) | H3···Br1xiv | 3.555 |
C2···C10iv | 3.470 (4) | H3···O1xv | 2.968 |
C8···O1v | 3.517 (3) | H3···C2iii | 3.483 |
C8···C16iv | 3.427 (4) | H3···C9x | 3.283 |
C9···O1v | 3.318 (4) | H3···H2iii | 3.091 |
C10···C2iv | 3.470 (4) | H3···H4xi | 3.486 |
C16···C8iv | 3.427 (4) | H3···H5xi | 3.311 |
Br1···H1vi | 3.230 | H3···H7x | 2.888 |
Br1···H2vi | 3.276 | H3···H8iv | 3.241 |
Br1···H3vii | 3.555 | H4···Br1xiv | 3.515 |
Br1···H4vii | 3.515 | H4···Br1iv | 3.556 |
Br1···H4iv | 3.556 | H4···C4xi | 3.069 |
Br1···H5iv | 3.328 | H4···H3xi | 3.486 |
Br1···H6iv | 3.568 | H4···H4xi | 2.163 |
Br1···H7ii | 3.550 | H5···Br1iv | 3.328 |
Br1···H8viii | 3.506 | H5···H3xi | 3.311 |
Br1···H9viii | 3.333 | H6···Br1iv | 3.568 |
O1···H3ix | 2.968 | H6···O1v | 2.993 |
O1···H6ii | 2.993 | H6···C16iv | 3.520 |
O1···H7ii | 2.587 | H6···H1v | 3.414 |
C2···H2iii | 3.192 | H6···H6xvi | 3.240 |
C2···H3iii | 3.483 | H6···H11iv | 2.952 |
C2···H8iv | 3.056 | H7···Br1v | 3.550 |
C3···H2iii | 3.152 | H7···O1v | 2.587 |
C3···H7x | 3.475 | H7···C3xii | 3.475 |
C3···H8iv | 3.198 | H7···C10xiii | 3.381 |
C4···H4xi | 3.069 | H7···C15v | 3.574 |
C5···H10iv | 3.521 | H7···H2xii | 3.182 |
C7···H10iv | 3.199 | H7···H2iv | 3.336 |
C7···H11iv | 3.403 | H7···H3xii | 2.888 |
C8···H10iv | 3.328 | H7···H8xiii | 2.457 |
C8···H11iv | 2.846 | H7···H11iv | 3.159 |
C9···H2xii | 3.178 | H8···Br1viii | 3.506 |
C9···H3xii | 3.283 | H8···C2iv | 3.056 |
C9···H8xiii | 3.142 | H8···C3iv | 3.198 |
C9···H11iv | 2.985 | H8···C9xiii | 3.142 |
C10···H2xii | 3.009 | H8···C10xiii | 3.298 |
C10···H2iv | 3.534 | H8···H2xii | 2.883 |
C10···H7xiii | 3.381 | H8···H2iv | 3.025 |
C10···H8xiii | 3.298 | H8···H3iv | 3.241 |
C12···H10iv | 3.525 | H8···H7xiii | 2.457 |
C15···H7ii | 3.574 | H8···H8xiii | 2.774 |
C16···H6iv | 3.520 | H9···Br1viii | 3.333 |
H1···Br1vi | 3.230 | H10···C5iv | 3.521 |
H1···H6ii | 3.414 | H10···C7iv | 3.199 |
H2···Br1vi | 3.276 | H10···C8iv | 3.328 |
H2···C2iii | 3.192 | H10···C12iv | 3.525 |
H2···C3iii | 3.152 | H10···H10iv | 3.309 |
H2···C9x | 3.178 | H11···C7iv | 3.403 |
H2···C10x | 3.009 | H11···C8iv | 2.846 |
H2···C10iv | 3.534 | H11···C9iv | 2.985 |
H2···H2iii | 3.138 | H11···H6iv | 2.952 |
H2···H3iii | 3.091 | H11···H7iv | 3.159 |
H2···H7x | 3.182 | H11···H11vi | 3.572 |
H2···H7iv | 3.336 | | |
| | | |
C2—C1—C14 | 120.7 (2) | O1—C15—C13 | 122.6 (2) |
C1—C2—C3 | 119.7 (2) | O1—C15—C16 | 121.4 (2) |
C2—C3—C4 | 119.9 (2) | C13—C15—C16 | 115.9 (2) |
C3—C4—C5 | 121.2 (2) | Br1—C16—C15 | 111.7 (2) |
C4—C5—C6 | 122.5 (2) | C2—C1—H1 | 119.7 |
C4—C5—C14 | 119.3 (2) | C14—C1—H1 | 119.6 |
C6—C5—C14 | 118.1 (2) | C1—C2—H2 | 120.2 |
C5—C6—C7 | 108.58 (18) | C3—C2—H2 | 120.2 |
C5—C6—C13i | 111.8 (2) | C2—C3—H3 | 120.1 |
C7—C6—C13i | 111.8 (2) | C4—C3—H3 | 120.1 |
C6—C7—C8 | 122.2 (2) | C3—C4—H4 | 119.4 |
C6—C7—C12 | 117.6 (2) | C5—C4—H4 | 119.4 |
C8—C7—C12 | 120.1 (2) | C5—C6—H5 | 108.2 |
C7—C8—C9 | 120.2 (2) | C7—C6—H5 | 108.2 |
C8—C9—C10 | 119.6 (2) | C13i—C6—H5 | 108.2 |
C9—C10—C11 | 120.3 (2) | C7—C8—H6 | 119.9 |
C10—C11—C12 | 120.8 (2) | C9—C8—H6 | 119.9 |
C7—C12—C11 | 118.9 (2) | C8—C9—H7 | 120.2 |
C7—C12—C13 | 117.30 (18) | C10—C9—H7 | 120.2 |
C11—C12—C13 | 123.7 (2) | C9—C10—H8 | 119.8 |
C6i—C13—C12 | 110.60 (18) | C11—C10—H8 | 119.8 |
C6i—C13—C14 | 110.18 (17) | C10—C11—H9 | 119.6 |
C6i—C13—C15 | 109.9 (2) | C12—C11—H9 | 119.6 |
C12—C13—C14 | 108.4 (2) | Br1—C16—H10 | 109.3 |
C12—C13—C15 | 108.77 (17) | Br1—C16—H11 | 109.3 |
C14—C13—C15 | 109.01 (18) | C15—C16—H10 | 109.3 |
C1—C14—C5 | 119.2 (2) | C15—C16—H11 | 109.3 |
C1—C14—C13 | 123.9 (2) | H10—C16—H11 | 107.9 |
C5—C14—C13 | 116.60 (19) | | |
| | | |
C2—C1—C14—C5 | 3.1 (3) | C8—C7—C12—C11 | 1.7 (3) |
C2—C1—C14—C13 | 176.9 (2) | C8—C7—C12—C13 | 177.4 (2) |
C14—C1—C2—C3 | −0.6 (4) | C12—C7—C8—C9 | 0.3 (4) |
C1—C2—C3—C4 | −1.7 (4) | C7—C8—C9—C10 | −1.4 (4) |
C2—C3—C4—C5 | 1.6 (4) | C8—C9—C10—C11 | 0.5 (4) |
C3—C4—C5—C6 | −175.2 (2) | C9—C10—C11—C12 | 1.5 (4) |
C3—C4—C5—C14 | 0.8 (4) | C10—C11—C12—C7 | −2.6 (4) |
C4—C5—C6—C7 | −138.9 (2) | C10—C11—C12—C13 | −178.0 (2) |
C4—C5—C6—C13i | 97.3 (3) | C7—C12—C13—C6i | −77.2 (2) |
C4—C5—C14—C1 | −3.1 (3) | C7—C12—C13—C14 | 43.6 (2) |
C4—C5—C14—C13 | −177.4 (2) | C7—C12—C13—C15 | 162.0 (2) |
C6—C5—C14—C1 | 173.1 (2) | C11—C12—C13—C6i | 98.2 (2) |
C6—C5—C14—C13 | −1.2 (3) | C11—C12—C13—C14 | −140.9 (2) |
C14—C5—C6—C7 | 45.0 (3) | C11—C12—C13—C15 | −22.6 (3) |
C14—C5—C6—C13i | −78.8 (2) | C6i—C13—C14—C1 | −95.7 (2) |
C5—C6—C7—C8 | 138.3 (2) | C6i—C13—C14—C5 | 78.3 (2) |
C5—C6—C7—C12 | −44.3 (3) | C6i—C13—C15—O1 | −0.0 (2) |
C5—C6—C13i—C12i | 1.3 (2) | C6i—C13—C15—C16 | 178.56 (17) |
C5—C6—C13i—C14i | 121.0 (2) | C12—C13—C14—C1 | 143.2 (2) |
C5—C6—C13i—C15i | −118.8 (2) | C12—C13—C14—C5 | −42.8 (2) |
C7—C6—C13i—C12i | −120.7 (2) | C12—C13—C15—O1 | 121.2 (2) |
C7—C6—C13i—C14i | −1.0 (3) | C12—C13—C15—C16 | −60.2 (2) |
C7—C6—C13i—C15i | 119.2 (2) | C14—C13—C15—O1 | −120.8 (2) |
C13i—C6—C7—C8 | −97.8 (3) | C14—C13—C15—C16 | 57.7 (2) |
C13i—C6—C7—C12 | 79.5 (2) | C15—C13—C14—C1 | 25.0 (3) |
C6—C7—C8—C9 | 177.5 (2) | C15—C13—C14—C5 | −161.1 (2) |
C6—C7—C12—C11 | −175.7 (2) | O1—C15—C16—Br1 | −30.8 (2) |
C6—C7—C12—C13 | −0.0 (3) | C13—C15—C16—Br1 | 150.67 (16) |
Symmetry codes: (i) −x+1, −y, −z+2; (ii) x, y+1, z; (iii) −x+1, −y+1, −z+1; (iv) −x, −y, −z+2; (v) x, y−1, z; (vi) −x, −y+1, −z+2; (vii) x−1, y, z+1; (viii) −x, −y, −z+3; (ix) x, y, z+1; (x) x, y+1, z−1; (xi) −x+1, −y, −z+1; (xii) x, y−1, z+1; (xiii) −x, −y−1, −z+3; (xiv) x+1, y, z−1; (xv) x, y, z−1; (xvi) −x+1, −y−1, −z+2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C9—H7···O1v | 0.95 | 2.59 | 3.318 (4) | 134 |
Symmetry code: (v) x, y−1, z. |
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