9-(Bromo­acet­yl)anthracene dimer

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], C₃₂H₂₂Br₂O₂, is a [4+4] photodimer of 9-(bromo­acet­yl)anthracene. The molecule is centrosymmetric and contains a long Csp³—Csp³ bond of 1.619 (3) Å. Inter­molecular C—H...O inter­actions are observed.

Key indicators

• Single-crystal X-ray study
• T = 153 K
• Mean [sigma](C-C)= 0.003 Å
• R factor = 0.036
• wR factor = 0.074
• Data-to-parameter ratio = 16.9

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Computing details

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

Crystal data

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) Å^3

Data collection

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

Refinement on F^2	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.036	w = 1/[σ^2(Fo^2) + (0.0139P)^2 + 0.9661P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 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

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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—C13^i	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···C8^ii	3.517 (3)	H2···H8^x	2.883
O1···C9^ii	3.318 (4)	H2···H8^iv	3.025
C2···C2^iii	3.512 (3)	H3···Br1^xiv	3.555
C2···C10^iv	3.470 (4)	H3···O1^xv	2.968
C8···O1^v	3.517 (3)	H3···C2^iii	3.483
C8···C16^iv	3.427 (4)	H3···C9^x	3.283
C9···O1^v	3.318 (4)	H3···H2^iii	3.091
C10···C2^iv	3.470 (4)	H3···H4^xi	3.486
C16···C8^iv	3.427 (4)	H3···H5^xi	3.311
Br1···H1^vi	3.230	H3···H7^x	2.888
Br1···H2^vi	3.276	H3···H8^iv	3.241
Br1···H3^vii	3.555	H4···Br1^xiv	3.515
Br1···H4^vii	3.515	H4···Br1^iv	3.556
Br1···H4^iv	3.556	H4···C4^xi	3.069
Br1···H5^iv	3.328	H4···H3^xi	3.486
Br1···H6^iv	3.568	H4···H4^xi	2.163
Br1···H7^ii	3.550	H5···Br1^iv	3.328
Br1···H8^viii	3.506	H5···H3^xi	3.311
Br1···H9^viii	3.333	H6···Br1^iv	3.568
O1···H3^ix	2.968	H6···O1^v	2.993
O1···H6^ii	2.993	H6···C16^iv	3.520
O1···H7^ii	2.587	H6···H1^v	3.414
C2···H2^iii	3.192	H6···H6^xvi	3.240
C2···H3^iii	3.483	H6···H11^iv	2.952
C2···H8^iv	3.056	H7···Br1^v	3.550
C3···H2^iii	3.152	H7···O1^v	2.587
C3···H7^x	3.475	H7···C3^xii	3.475
C3···H8^iv	3.198	H7···C10^xiii	3.381
C4···H4^xi	3.069	H7···C15^v	3.574
C5···H10^iv	3.521	H7···H2^xii	3.182
C7···H10^iv	3.199	H7···H2^iv	3.336
C7···H11^iv	3.403	H7···H3^xii	2.888
C8···H10^iv	3.328	H7···H8^xiii	2.457
C8···H11^iv	2.846	H7···H11^iv	3.159
C9···H2^xii	3.178	H8···Br1^viii	3.506
C9···H3^xii	3.283	H8···C2^iv	3.056
C9···H8^xiii	3.142	H8···C3^iv	3.198
C9···H11^iv	2.985	H8···C9^xiii	3.142
C10···H2^xii	3.009	H8···C10^xiii	3.298
C10···H2^iv	3.534	H8···H2^xii	2.883
C10···H7^xiii	3.381	H8···H2^iv	3.025
C10···H8^xiii	3.298	H8···H3^iv	3.241
C12···H10^iv	3.525	H8···H7^xiii	2.457
C15···H7^ii	3.574	H8···H8^xiii	2.774
C16···H6^iv	3.520	H9···Br1^viii	3.333
H1···Br1^vi	3.230	H10···C5^iv	3.521
H1···H6^ii	3.414	H10···C7^iv	3.199
H2···Br1^vi	3.276	H10···C8^iv	3.328
H2···C2^iii	3.192	H10···C12^iv	3.525
H2···C3^iii	3.152	H10···H10^iv	3.309
H2···C9^x	3.178	H11···C7^iv	3.403
H2···C10^x	3.009	H11···C8^iv	2.846
H2···C10^iv	3.534	H11···C9^iv	2.985
H2···H2^iii	3.138	H11···H6^iv	2.952
H2···H3^iii	3.091	H11···H7^iv	3.159
H2···H7^x	3.182	H11···H11^vi	3.572
H2···H7^iv	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—C13^i	111.8 (2)	C2—C3—H3	120.1
C7—C6—C13^i	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)	C13^i—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
C6^i—C13—C12	110.60 (18)	C11—C10—H8	119.8
C6^i—C13—C14	110.18 (17)	C10—C11—H9	119.6
C6^i—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—C13^i	97.3 (3)	C7—C12—C13—C6^i	−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—C6^i	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—C13^i	−78.8 (2)	C6^i—C13—C14—C1	−95.7 (2)
C5—C6—C7—C8	138.3 (2)	C6^i—C13—C14—C5	78.3 (2)
C5—C6—C7—C12	−44.3 (3)	C6^i—C13—C15—O1	−0.0 (2)
C5—C6—C13^i—C12^i	1.3 (2)	C6^i—C13—C15—C16	178.56 (17)
C5—C6—C13^i—C14^i	121.0 (2)	C12—C13—C14—C1	143.2 (2)
C5—C6—C13^i—C15^i	−118.8 (2)	C12—C13—C14—C5	−42.8 (2)
C7—C6—C13^i—C12^i	−120.7 (2)	C12—C13—C15—O1	121.2 (2)
C7—C6—C13^i—C14^i	−1.0 (3)	C12—C13—C15—C16	−60.2 (2)
C7—C6—C13^i—C15^i	119.2 (2)	C14—C13—C15—O1	−120.8 (2)
C13^i—C6—C7—C8	−97.8 (3)	C14—C13—C15—C16	57.7 (2)
C13^i—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)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H7···O1^v	0.95	2.59	3.318 (4)	134

Symmetry code: (v) x, y−1, z.