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The title compound, C11H9Br3, consists of a norbornane skeleton, composed of two five-membered rings in envelope conformations and a six-membered ring with three Br atoms held in a boat conformation by a bridging methylene group, which constitutes a bicyclo[2.2.1]heptane system, having a benzene ring fused on one side. The repulsive interactions between the Br atoms affect the topology of the norbornane skeleton.
Supporting information
CCDC reference: 263673
Key indicators
- Single-crystal X-ray study
- T = 297 K
- Mean (C-C) = 0.007 Å
- R factor = 0.033
- wR factor = 0.066
- Data-to-parameter ratio = 16.5
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT164_ALERT_4_C Nr. of Refined C-H H-Atoms in Heavy-At Struct... 9
PLAT350_ALERT_3_C Short C-H Bond (0.96A) C2 - H2 ... 0.83 Ang.
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
2 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
0 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
1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); 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).
(±)-(1SR,8RS,10RS)-9,9,10-Tribromotricyclo[6.2.1.0
2,7]undeca-2,4,6-triene
top
Crystal data top
C11H9Br3 | F(000) = 1440 |
Mr = 380.91 | Dx = 2.219 Mg m−3 |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 2676 reflections |
a = 7.4853 (17) Å | θ = 3–25° |
b = 13.449 (3) Å | µ = 10.57 mm−1 |
c = 22.653 (5) Å | T = 297 K |
V = 2280.5 (9) Å3 | Prism, colourless |
Z = 8 | 0.40 × 0.28 × 0.14 mm |
Data collection top
Bruker SMART CCD area-detector diffractometer | 2690 independent reflections |
Radiation source: fine-focus sealed tube | 1562 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.077 |
φ and ω scans | θmax = 28.0°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −9→9 |
Tmin = 0.039, Tmax = 0.225 | k = −17→17 |
12253 measured reflections | l = −29→19 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.033 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.066 | All H-atom parameters refined |
S = 0.82 | w = 1/[σ2(Fo2) + (0.0251P)2] where P = (Fo2 + 2Fc2)/3 |
2690 reflections | (Δ/σ)max < 0.001 |
163 parameters | Δρmax = 0.50 e Å−3 |
0 restraints | Δρmin = −0.62 e Å−3 |
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 | |
Br1 | 0.32845 (7) | 0.14380 (3) | 0.19290 (2) | 0.05873 (17) | |
Br2 | 0.24003 (6) | 0.33247 (3) | 0.11818 (2) | 0.04691 (15) | |
Br3 | 0.52421 (6) | 0.44725 (3) | 0.20837 (2) | 0.05224 (16) | |
C1 | 0.7409 (5) | 0.3505 (3) | 0.09716 (19) | 0.0326 (10) | |
C2 | 0.8170 (6) | 0.4359 (3) | 0.0760 (3) | 0.0434 (13) | |
C3 | 0.7766 (6) | 0.4675 (4) | 0.0198 (3) | 0.0484 (13) | |
C4 | 0.6593 (7) | 0.4147 (4) | −0.0143 (2) | 0.0515 (14) | |
C5 | 0.5788 (6) | 0.3284 (3) | 0.0067 (2) | 0.0424 (12) | |
C6 | 0.6217 (5) | 0.2971 (3) | 0.06245 (19) | 0.0301 (10) | |
C7 | 0.5565 (6) | 0.2111 (3) | 0.0989 (2) | 0.0338 (11) | |
C8 | 0.7272 (6) | 0.1885 (3) | 0.1352 (2) | 0.0378 (11) | |
C9 | 0.7527 (6) | 0.2955 (3) | 0.1557 (2) | 0.0350 (11) | |
C10 | 0.5750 (6) | 0.3099 (3) | 0.1894 (2) | 0.0326 (10) | |
C11 | 0.4367 (5) | 0.2544 (3) | 0.14854 (18) | 0.0341 (10) | |
H2 | 0.886 (5) | 0.471 (2) | 0.0960 (16) | 0.019 (11)* | |
H3 | 0.811 (5) | 0.533 (3) | 0.0050 (18) | 0.043 (12)* | |
H4 | 0.634 (5) | 0.435 (3) | −0.0494 (18) | 0.036 (13)* | |
H5 | 0.498 (5) | 0.291 (3) | −0.0168 (18) | 0.032 (11)* | |
H7 | 0.507 (5) | 0.160 (3) | 0.0771 (17) | 0.035 (11)* | |
H9 | 0.854 (5) | 0.308 (2) | 0.1764 (17) | 0.029 (11)* | |
H10 | 0.573 (5) | 0.277 (3) | 0.2268 (19) | 0.051 (14)* | |
H81 | 0.827 (5) | 0.167 (3) | 0.1103 (18) | 0.045 (12)* | |
H82 | 0.718 (5) | 0.138 (3) | 0.165 (2) | 0.051 (13)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Br1 | 0.0754 (4) | 0.0447 (3) | 0.0560 (4) | −0.0148 (3) | 0.0202 (3) | 0.0106 (3) |
Br2 | 0.0323 (2) | 0.0561 (3) | 0.0524 (3) | 0.0059 (2) | −0.0029 (2) | 0.0007 (3) |
Br3 | 0.0544 (3) | 0.0418 (3) | 0.0605 (4) | 0.0027 (2) | 0.0033 (3) | −0.0210 (2) |
C1 | 0.027 (2) | 0.037 (2) | 0.034 (3) | 0.0077 (19) | 0.0039 (19) | −0.001 (2) |
C2 | 0.032 (2) | 0.035 (3) | 0.064 (4) | −0.002 (2) | 0.003 (3) | 0.000 (3) |
C3 | 0.048 (3) | 0.043 (3) | 0.054 (4) | 0.006 (2) | 0.013 (3) | 0.021 (3) |
C4 | 0.057 (3) | 0.069 (4) | 0.028 (3) | 0.016 (3) | 0.010 (3) | 0.020 (3) |
C5 | 0.043 (3) | 0.054 (3) | 0.030 (3) | 0.004 (2) | 0.005 (2) | −0.001 (3) |
C6 | 0.029 (2) | 0.035 (2) | 0.026 (3) | 0.0023 (17) | 0.005 (2) | −0.002 (2) |
C7 | 0.041 (3) | 0.028 (2) | 0.033 (3) | 0.0028 (19) | −0.003 (2) | −0.007 (2) |
C8 | 0.045 (3) | 0.031 (2) | 0.037 (3) | 0.011 (2) | 0.004 (2) | 0.003 (2) |
C9 | 0.031 (2) | 0.043 (3) | 0.031 (3) | 0.003 (2) | −0.007 (2) | −0.004 (2) |
C10 | 0.042 (3) | 0.030 (2) | 0.026 (3) | 0.0002 (18) | −0.001 (2) | −0.001 (2) |
C11 | 0.038 (2) | 0.031 (2) | 0.034 (3) | −0.0011 (18) | 0.004 (2) | 0.008 (2) |
Geometric parameters (Å, º) top
Br1—C11 | 1.970 (4) | C8—C9 | 1.524 (6) |
Br2—C11 | 1.934 (4) | C9—C10 | 1.546 (6) |
Br3—C10 | 1.935 (4) | C10—C11 | 1.576 (6) |
C1—C2 | 1.369 (6) | C2—H2 | 0.83 (3) |
C1—C6 | 1.389 (5) | C3—H3 | 0.98 (4) |
C1—C9 | 1.521 (6) | C4—H4 | 0.86 (4) |
C2—C3 | 1.376 (7) | C5—H5 | 0.96 (4) |
C3—C4 | 1.368 (7) | C7—H7 | 0.93 (4) |
C4—C5 | 1.392 (6) | C8—H81 | 0.98 (4) |
C5—C6 | 1.369 (6) | C8—H82 | 0.96 (4) |
C6—C7 | 1.502 (5) | C9—H9 | 0.91 (4) |
C7—C8 | 1.550 (6) | C10—H10 | 0.96 (4) |
C7—C11 | 1.552 (6) | | |
| | | |
C2—C1—C6 | 120.2 (4) | C10—C11—Br1 | 109.2 (3) |
C2—C1—C9 | 133.6 (4) | Br2—C11—Br1 | 106.16 (19) |
C6—C1—C9 | 106.2 (4) | C1—C2—H2 | 123 (3) |
C1—C2—C3 | 119.5 (5) | C3—C2—H2 | 118 (3) |
C4—C3—C2 | 120.2 (5) | C4—C3—H3 | 116 (2) |
C3—C4—C5 | 121.2 (5) | C2—C3—H3 | 122 (2) |
C6—C5—C4 | 118.1 (5) | C3—C4—H4 | 120 (3) |
C5—C6—C1 | 120.9 (4) | C5—C4—H4 | 119 (3) |
C5—C6—C7 | 131.8 (4) | C6—C5—H5 | 120 (2) |
C1—C6—C7 | 107.2 (4) | C4—C5—H5 | 122 (2) |
C6—C7—C8 | 100.0 (3) | C6—C7—H7 | 114 (2) |
C6—C7—C11 | 107.3 (3) | C8—C7—H7 | 118 (2) |
C8—C7—C11 | 99.5 (3) | C11—C7—H7 | 116 (2) |
C9—C8—C7 | 94.6 (3) | C9—C8—H81 | 111 (2) |
C1—C9—C8 | 100.7 (4) | C7—C8—H81 | 112 (2) |
C1—C9—C10 | 108.6 (4) | C9—C8—H82 | 118 (3) |
C8—C9—C10 | 99.2 (4) | C7—C8—H82 | 117 (2) |
C9—C10—C11 | 102.5 (3) | H81—C8—H82 | 104 (3) |
C9—C10—Br3 | 113.5 (3) | C1—C9—H9 | 114 (2) |
C11—C10—Br3 | 117.0 (3) | C8—C9—H9 | 116 (2) |
C7—C11—C10 | 102.9 (3) | C10—C9—H9 | 116 (2) |
C7—C11—Br2 | 112.7 (3) | C9—C10—H10 | 113 (3) |
C10—C11—Br2 | 116.9 (3) | C11—C10—H10 | 107 (3) |
C7—C11—Br1 | 108.9 (3) | Br3—C10—H10 | 104 (3) |
| | | |
C6—C1—C2—C3 | −1.0 (6) | C11—C7—C8—C9 | −58.3 (4) |
C9—C1—C2—C3 | −179.1 (4) | C1—C9—C8—C7 | −50.7 (4) |
C2—C1—C6—C5 | 0.2 (6) | C10—C9—C8—C7 | 60.4 (4) |
C2—C1—C6—C7 | −177.5 (4) | C1—C9—C10—C11 | 65.1 (4) |
C2—C1—C9—C8 | −148.9 (5) | C1—C9—C10—Br3 | −61.9 (4) |
C2—C1—C9—C10 | 107.5 (5) | C8—C9—C10—C11 | −39.5 (4) |
C6—C1—C9—C8 | 32.8 (4) | C8—C9—C10—Br3 | −166.6 (3) |
C6—C1—C9—C10 | −70.9 (4) | C10—C11—C7—C6 | −69.8 (4) |
C9—C1—C6—C5 | 178.8 (4) | C10—C11—C7—C8 | 33.9 (4) |
C9—C1—C6—C7 | 1.2 (4) | Br1—C11—C7—C6 | 174.5 (3) |
C1—C2—C3—C4 | 0.9 (7) | Br1—C11—C7—C8 | −81.8 (3) |
C2—C3—C4—C5 | 0.0 (7) | Br2—C11—C7—C6 | 57.0 (4) |
C6—C5—C4—C3 | −0.7 (7) | Br2—C11—C7—C8 | 160.7 (3) |
C1—C6—C5—C4 | 0.7 (6) | C7—C11—C10—C9 | 3.0 (4) |
C7—C6—C5—C4 | 177.6 (4) | C7—C11—C10—Br3 | 127.8 (3) |
C1—C6—C7—C8 | −34.0 (4) | Br1—C11—C10—C9 | 118.5 (3) |
C1—C6—C7—C11 | 69.4 (4) | Br1—C11—C10—Br3 | −116.7 (3) |
C5—C6—C7—C8 | 148.7 (4) | Br2—C11—C10—C9 | −121.1 (3) |
C5—C6—C7—C11 | −107.9 (5) | Br2—C11—C10—Br3 | 3.7 (4) |
C6—C7—C8—C9 | 51.3 (4) | | |
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