(1RS,8SR,9RS,10RS,11RS,12RS)-10,11-Di­bromo­tetra­cyclo­[6.4.2.0^2,7.0^9,12]tetradeca-2,4,6,13-tetraene

The title compound, C₁₄H₁₂Br₂, consists of two central non-coplanar six-membered carbon rings constituting a bicyclic system, having a benzene ring fused on one side and a brominated cyclo­butane ring fused on the other side at the bridging atoms of the bicyclic system. The bicyclic system has approximate D₃ symmetry and all three six-membered rings adopt boat conformations.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.036
• wR factor = 0.082
• Data-to-parameter ratio = 18.9

checkCIF/PLATON results

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Computing details

Data collection: SMART (Bruker, 1999); cell refinement: SMART; data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

(I)

Crystal data

C14H12Br2	F(000) = 664
Mr = 340.06	Dx = 1.880 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3489 reflections
a = 11.7056 (9) Å	θ = 2.3–26.0°
b = 6.9920 (5) Å	µ = 6.71 mm^−1
c = 14.6897 (11) Å	T = 293 K
β = 92.052 (1)°	Prism, colourless
V = 1201.52 (15) Å^3	0.35 × 0.19 × 0.17 mm
Z = 4

Data collection

Nonius KappaCCD diffractometer	2758 independent reflections
Radiation source: sealed tube	1916 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.048
φ and ω scans	θmax = 28.0°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→15
Tmin = 0.236, Tmax = 0.319	k = −9→9
6990 measured reflections	l = −19→17

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.036	H-atom parameters constrained
wR(F^2) = 0.082	w = 1/[σ^2(Fo^2) + (0.0408P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.91	(Δ/σ)max < 0.001
2758 reflections	Δρmax = 0.70 e Å^−3
146 parameters	Δρmin = −0.67 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0176 (7)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Br1	0.04675 (3)	0.21188 (6)	0.68272 (2)	0.04228 (15)
Br2	0.17139 (3)	0.27573 (6)	0.41402 (2)	0.04148 (14)
C1	0.3882 (3)	0.7672 (4)	0.5815 (2)	0.0295 (7)
C2	0.4983 (3)	0.8337 (5)	0.5798 (2)	0.0357 (8)
C3	0.5373 (3)	0.9628 (5)	0.6460 (2)	0.0413 (9)
C4	0.4666 (3)	1.0211 (5)	0.7132 (2)	0.0414 (9)
C5	0.3552 (3)	0.9511 (5)	0.7163 (2)	0.0379 (9)
C6	0.3157 (3)	0.8248 (4)	0.6494 (2)	0.0301 (7)
C7	0.1968 (3)	0.7385 (4)	0.6403 (2)	0.0322 (8)
C8	0.1543 (3)	0.7794 (5)	0.5436 (3)	0.0373 (9)
C9	0.2216 (3)	0.7210 (5)	0.4800 (2)	0.0346 (8)
C10	0.3308 (3)	0.6277 (5)	0.5138 (2)	0.0296 (7)
C11	0.3004 (3)	0.4534 (5)	0.5748 (2)	0.0279 (7)
C12	0.2132 (3)	0.3012 (5)	0.5434 (2)	0.0303 (7)
C13	0.1240 (3)	0.3892 (5)	0.6028 (2)	0.0314 (8)
C14	0.2170 (3)	0.5199 (5)	0.6475 (2)	0.0304 (8)
H2	0.5466	0.7927	0.5348	0.043*
H3	0.6116	1.0098	0.6447	0.050*
H4	0.4931	1.1080	0.7570	0.050*
H5	0.3079	0.9886	0.7626	0.045*
H7	0.1452	0.7867	0.6861	0.039*
H8	0.0854	0.8414	0.5305	0.045*
H9	0.2032	0.7361	0.4183	0.041*
H10	0.3806	0.5925	0.4643	0.036*
H11	0.3692	0.3950	0.6028	0.033*
H12	0.2363	0.1763	0.5681	0.036*
H13	0.0686	0.4642	0.5662	0.038*
H14	0.2405	0.4790	0.7092	0.036*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0450 (2)	0.0475 (3)	0.0345 (2)	−0.00734 (17)	0.00426 (18)	0.00652 (16)
Br2	0.0478 (2)	0.0508 (3)	0.0255 (2)	−0.00828 (18)	−0.00284 (17)	−0.00714 (16)
C1	0.0353 (18)	0.0281 (18)	0.0246 (17)	−0.0009 (14)	−0.0065 (15)	0.0019 (13)
C2	0.0376 (19)	0.040 (2)	0.0289 (19)	−0.0021 (16)	−0.0006 (16)	0.0007 (15)
C3	0.038 (2)	0.038 (2)	0.047 (2)	−0.0092 (17)	−0.0128 (19)	0.0051 (18)
C4	0.056 (2)	0.029 (2)	0.037 (2)	−0.0044 (18)	−0.016 (2)	−0.0053 (16)
C5	0.052 (2)	0.030 (2)	0.0313 (19)	0.0042 (17)	−0.0021 (18)	−0.0058 (15)
C6	0.0370 (18)	0.0255 (19)	0.0273 (17)	0.0026 (15)	−0.0040 (15)	0.0011 (14)
C7	0.0328 (17)	0.032 (2)	0.0319 (18)	0.0036 (15)	0.0060 (16)	−0.0051 (14)
C8	0.0338 (18)	0.0274 (19)	0.050 (2)	0.0004 (16)	−0.0136 (18)	0.0055 (16)
C9	0.042 (2)	0.034 (2)	0.0272 (18)	−0.0025 (16)	−0.0130 (17)	0.0065 (14)
C10	0.0332 (18)	0.033 (2)	0.0221 (17)	−0.0033 (15)	−0.0017 (15)	−0.0022 (14)
C11	0.0304 (17)	0.0290 (18)	0.0237 (17)	0.0035 (14)	−0.0075 (14)	−0.0020 (13)
C12	0.0385 (18)	0.0306 (19)	0.0214 (16)	−0.0037 (15)	−0.0055 (15)	0.0010 (13)
C13	0.0352 (18)	0.032 (2)	0.0266 (17)	−0.0018 (15)	−0.0023 (15)	0.0052 (14)
C14	0.0341 (17)	0.035 (2)	0.0218 (16)	0.0002 (15)	−0.0056 (15)	−0.0009 (14)

Geometric parameters (Å, º)

Br1—C13	1.952 (3)	C13—H13	0.9800
Br2—C12	1.954 (3)	C14—C11	1.545 (4)
C8—C9	1.310 (5)	C14—C7	1.550 (4)
C8—C7	1.514 (5)	C14—H14	0.9800
C8—H8	0.9300	C7—H7	0.9800
C9—C10	1.504 (5)	C10—C11	1.561 (4)
C9—H9	0.9300	C10—H10	0.9800
C12—C13	1.515 (5)	C2—C3	1.392 (5)
C12—C11	1.534 (4)	C2—H2	0.9300
C12—H12	0.9800	C5—C4	1.395 (5)
C1—C2	1.371 (5)	C5—H5	0.9300
C1—C6	1.392 (5)	C4—C3	1.373 (5)
C1—C10	1.531 (4)	C4—H4	0.9300
C6—C5	1.388 (4)	C11—H11	0.9800
C6—C7	1.518 (5)	C3—H3	0.9300
C13—C14	1.550 (4)
C9—C8—C7	115.1 (3)	C8—C7—C6	106.1 (3)
C9—C8—H8	122.4	C8—C7—C14	107.1 (3)
C7—C8—H8	122.4	C6—C7—C14	104.4 (3)
C8—C9—C10	115.2 (3)	C8—C7—H7	112.9
C8—C9—H9	122.4	C6—C7—H7	112.9
C10—C9—H9	122.4	C14—C7—H7	112.9
C13—C12—C11	90.6 (2)	C9—C10—C1	106.6 (3)
C13—C12—Br2	116.3 (2)	C9—C10—C11	108.6 (3)
C11—C12—Br2	119.7 (2)	C1—C10—C11	103.3 (2)
C13—C12—H12	109.6	C9—C10—H10	112.6
C11—C12—H12	109.6	C1—C10—H10	112.6
Br2—C12—H12	109.6	C11—C10—H10	112.6
C2—C1—C6	120.8 (3)	C1—C2—C3	119.5 (3)
C2—C1—C10	126.6 (3)	C1—C2—H2	120.2
C6—C1—C10	112.6 (3)	C3—C2—H2	120.2
C5—C6—C1	119.7 (3)	C6—C5—C4	119.2 (3)
C5—C6—C7	126.6 (3)	C6—C5—H5	120.4
C1—C6—C7	113.8 (3)	C4—C5—H5	120.4
C12—C13—C14	89.7 (3)	C3—C4—C5	120.5 (3)
C12—C13—Br1	115.6 (2)	C3—C4—H4	119.7
C14—C13—Br1	117.0 (2)	C5—C4—H4	119.7
C12—C13—H13	111.0	C12—C11—C14	89.2 (2)
C14—C13—H13	111.0	C12—C11—C10	122.2 (3)
Br1—C13—H13	111.0	C14—C11—C10	108.9 (3)
C11—C14—C7	110.4 (3)	C12—C11—H11	111.4
C11—C14—C13	88.9 (2)	C14—C11—H11	111.4
C7—C14—C13	116.7 (3)	C10—C11—H11	111.4
C11—C14—H14	112.9	C4—C3—C2	120.2 (3)
C7—C14—H14	112.9	C4—C3—H3	119.9
C13—C14—H14	112.9	C2—C3—H3	119.9
C7—C8—C9—C10	−1.4 (4)	C8—C9—C10—C11	57.8 (4)
C2—C1—C6—C5	0.0 (5)	C2—C1—C10—C9	−127.2 (4)
C10—C1—C6—C5	179.8 (3)	C6—C1—C10—C9	53.0 (4)
C2—C1—C6—C7	179.6 (3)	C2—C1—C10—C11	118.4 (4)
C10—C1—C6—C7	−0.6 (4)	C6—C1—C10—C11	−61.4 (3)
C11—C12—C13—C14	−9.4 (2)	C6—C1—C2—C3	−1.1 (5)
Br2—C12—C13—C14	−133.4 (2)	C10—C1—C2—C3	179.1 (3)
C11—C12—C13—Br1	−129.5 (2)	C1—C6—C5—C4	1.3 (5)
Br2—C12—C13—Br1	106.6 (2)	C7—C6—C5—C4	−178.2 (3)
C12—C13—C14—C11	9.4 (2)	C6—C5—C4—C3	−1.4 (5)
Br1—C13—C14—C11	128.2 (2)	C13—C12—C11—C14	9.5 (2)
C12—C13—C14—C7	121.7 (3)	Br2—C12—C11—C14	130.6 (2)
Br1—C13—C14—C7	−119.4 (3)	C13—C12—C11—C10	−102.5 (3)
C9—C8—C7—C6	54.6 (4)	Br2—C12—C11—C10	18.6 (4)
C9—C8—C7—C14	−56.5 (4)	C7—C14—C11—C12	−127.4 (3)
C5—C6—C7—C8	127.4 (3)	C13—C14—C11—C12	−9.2 (2)
C1—C6—C7—C8	−52.1 (4)	C7—C14—C11—C10	−3.5 (3)
C5—C6—C7—C14	−119.6 (3)	C13—C14—C11—C10	114.7 (3)
C1—C6—C7—C14	60.9 (4)	C9—C10—C11—C12	49.8 (4)
C11—C14—C7—C8	56.1 (3)	C1—C10—C11—C12	162.8 (3)
C13—C14—C7—C8	−43.3 (4)	C9—C10—C11—C14	−51.6 (3)
C11—C14—C7—C6	−56.1 (3)	C1—C10—C11—C14	61.3 (3)
C13—C14—C7—C6	−155.6 (3)	C5—C4—C3—C2	0.4 (5)
C8—C9—C10—C1	−52.9 (4)	C1—C2—C3—C4	0.9 (5)