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The structure of the title compound, C10H8Br4O2, has been determined at room temperature. The ten-membered tetrahydronaphthalene ring system is nearly planar, with a total puckering amplitude QT of 0.386 (5) Å. The crystal structure is stabilized by short inter- and intramolecular hydrogen-bond contacts.
Supporting information
CCDC reference: 255927
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.007 Å
- R factor = 0.042
- wR factor = 0.082
- Data-to-parameter ratio = 21.3
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.64 mm
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7
PLAT354_ALERT_3_C Short O-H Bond (0.82A) O1 - HO1 ... 0.62 Ang.
PLAT354_ALERT_3_C Short O-H Bond (0.82A) O2 - HO2 ... 0.64 Ang.
PLAT431_ALERT_2_C Short Inter HL..A Contact Br1 .. Br2 .. 3.48 Ang.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 2
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
6 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
1 ALERT type 2 Indicator that the structure model may be wrong or deficient
4 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
trans,
trans,
trans-2,3,5,8-Tetrabromo-1,4-dihydroxy-1,2,3,4-
tetrahydronaphthalene
top
Crystal data top
C10H8Br4O2 | F(000) = 1792 |
Mr = 479.76 | Dx = 2.528 Mg m−3 |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 3257 reflections |
a = 16.8495 (9) Å | θ = 1.7–28.9° |
b = 12.1086 (9) Å | µ = 12.75 mm−1 |
c = 12.3570 (7) Å | T = 293 K |
V = 2521.1 (3) Å3 | Plate, colorless |
Z = 8 | 0.64 × 0.41 × 0.12 mm |
Data collection top
Stoe IPDS-II diffractometer | 3257 independent reflections |
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus | 2283 reflections with I > 2σ(I) |
Plane graphite monochromator | Rint = 0.089 |
Detector resolution: 6.67 pixels mm-1 | θmax = 28.8°, θmin = 2.4° |
ω scans | h = −22→22 |
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) | k = −16→15 |
Tmin = 0.045, Tmax = 0.310 | l = −13→16 |
15995 measured reflections | |
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)] = 0.042 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.082 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0198P)2 + 5.027P] where P = (Fo2 + 2Fc2)/3 |
3257 reflections | (Δ/σ)max = 0.001 |
153 parameters | Δρmax = 0.91 e Å−3 |
0 restraints | Δρmin = −0.73 e Å−3 |
Special details top
Geometry. Bond distances, angles etc. have been calculated using the rounded
fractional coordinates. All su's are estimated from the variances of the
(full) variance-covariance matrix. The cell e.s.d.'s are taken into account in
the estimation of distances, angles and torsion angles |
Refinement. Refinement on F2 for ALL reflections except those flagged by the user
for potential systematic errors. Weighted R-factors wR
and all goodnesses of fit S are based on F2,
conventional R-factors R are based on F, with F
set to zero for negative F2. The observed criterion of F2 >
σ(F2) is used only for calculating -R-factor-obs
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 | 0.97279 (3) | 0.83837 (4) | 0.46073 (4) | 0.0385 (2) | |
Br2 | 0.97835 (3) | 0.53826 (4) | 0.22988 (4) | 0.0411 (2) | |
Br3 | 0.79035 (4) | 0.42511 (5) | 0.56367 (6) | 0.0626 (2) | |
Br4 | 0.69346 (4) | 0.83661 (6) | 0.25087 (6) | 0.0621 (2) | |
O1 | 0.8645 (3) | 0.7469 (4) | 0.1800 (3) | 0.0396 (11) | |
O2 | 0.9393 (2) | 0.5910 (3) | 0.5489 (3) | 0.0416 (11) | |
C1 | 0.8691 (3) | 0.7629 (4) | 0.2944 (4) | 0.0287 (12) | |
C2 | 0.9543 (3) | 0.7447 (4) | 0.3320 (4) | 0.0303 (12) | |
C3 | 0.9735 (3) | 0.6266 (4) | 0.3647 (4) | 0.0297 (11) | |
C4 | 0.9144 (3) | 0.5721 (4) | 0.4411 (4) | 0.0295 (11) | |
C5 | 0.8294 (3) | 0.6072 (3) | 0.4220 (4) | 0.0283 (12) | |
C6 | 0.7682 (3) | 0.5481 (4) | 0.4738 (4) | 0.0403 (17) | |
C7 | 0.6890 (3) | 0.5742 (5) | 0.4602 (5) | 0.0533 (19) | |
C8 | 0.6691 (3) | 0.6602 (5) | 0.3929 (5) | 0.052 (2) | |
C9 | 0.7277 (3) | 0.7192 (4) | 0.3411 (4) | 0.0383 (17) | |
C10 | 0.8075 (3) | 0.6947 (3) | 0.3542 (4) | 0.0273 (12) | |
H1 | 0.85650 | 0.84070 | 0.30820 | 0.0340* | |
HO1 | 0.867 (6) | 0.698 (6) | 0.167 (7) | 0.09 (4)* | |
H2 | 0.99070 | 0.76750 | 0.27430 | 0.0360* | |
HO2 | 0.916 (4) | 0.630 (4) | 0.563 (5) | 0.036 (19)* | |
H3 | 1.02600 | 0.62550 | 0.39880 | 0.0360* | |
H4 | 0.91720 | 0.49230 | 0.42830 | 0.0350* | |
H7 | 0.64980 | 0.53420 | 0.49590 | 0.0640* | |
H8 | 0.61610 | 0.67860 | 0.38240 | 0.0620* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Br1 | 0.0441 (3) | 0.0369 (2) | 0.0346 (3) | −0.0062 (2) | −0.0047 (2) | −0.0034 (2) |
Br2 | 0.0530 (3) | 0.0353 (2) | 0.0351 (3) | 0.0038 (2) | 0.0128 (2) | −0.0024 (2) |
Br3 | 0.0734 (4) | 0.0474 (3) | 0.0669 (4) | −0.0074 (3) | 0.0240 (3) | 0.0210 (3) |
Br4 | 0.0521 (3) | 0.0739 (4) | 0.0602 (4) | 0.0243 (3) | −0.0131 (3) | 0.0098 (3) |
O1 | 0.047 (2) | 0.047 (2) | 0.0247 (18) | −0.0041 (19) | −0.0016 (15) | 0.0047 (17) |
O2 | 0.047 (2) | 0.049 (2) | 0.0289 (19) | 0.0149 (19) | 0.0012 (17) | 0.0040 (17) |
C1 | 0.032 (2) | 0.027 (2) | 0.027 (2) | −0.0020 (18) | −0.0029 (19) | 0.0030 (17) |
C2 | 0.029 (2) | 0.034 (2) | 0.028 (2) | −0.0012 (18) | 0.0021 (18) | 0.0018 (19) |
C3 | 0.0240 (19) | 0.035 (2) | 0.030 (2) | 0.0016 (18) | 0.0039 (19) | −0.0009 (18) |
C4 | 0.034 (2) | 0.0274 (19) | 0.027 (2) | 0.0042 (18) | 0.0075 (19) | 0.0028 (18) |
C5 | 0.030 (2) | 0.028 (2) | 0.027 (2) | 0.0005 (17) | 0.0040 (18) | −0.0011 (17) |
C6 | 0.044 (3) | 0.042 (3) | 0.035 (3) | −0.003 (2) | 0.009 (2) | 0.002 (2) |
C7 | 0.036 (3) | 0.062 (3) | 0.062 (4) | −0.016 (3) | 0.012 (3) | −0.001 (3) |
C8 | 0.026 (2) | 0.070 (4) | 0.060 (4) | −0.004 (3) | 0.001 (2) | −0.004 (3) |
C9 | 0.031 (3) | 0.045 (3) | 0.039 (3) | 0.004 (2) | −0.004 (2) | −0.004 (2) |
C10 | 0.026 (2) | 0.030 (2) | 0.026 (2) | 0.0019 (17) | −0.0038 (18) | −0.0032 (17) |
Geometric parameters (Å, º) top
Br1—C2 | 1.978 (5) | C5—C10 | 1.400 (6) |
Br2—C3 | 1.982 (5) | C5—C6 | 1.409 (7) |
Br3—C6 | 1.895 (5) | C6—C7 | 1.382 (7) |
Br4—C9 | 1.897 (5) | C7—C8 | 1.374 (9) |
O1—C1 | 1.429 (6) | C8—C9 | 1.377 (7) |
O2—C4 | 1.415 (6) | C9—C10 | 1.387 (7) |
O1—HO1 | 0.62 (7) | C1—H1 | 0.9800 |
O2—HO2 | 0.64 (6) | C2—H2 | 0.9800 |
C1—C2 | 1.525 (7) | C3—H3 | 0.9800 |
C1—C10 | 1.518 (7) | C4—H4 | 0.9800 |
C2—C3 | 1.521 (7) | C7—H7 | 0.9300 |
C3—C4 | 1.523 (7) | C8—H8 | 0.9300 |
C4—C5 | 1.513 (7) | | |
| | | |
Br1···O2 | 3.237 (4) | O2···Br1 | 3.237 (4) |
Br1···C5 | 3.729 (4) | O2···Br3 | 3.220 (4) |
Br1···Br2i | 3.6472 (7) | O2···C3iii | 3.200 (6) |
Br1···Br2ii | 3.4762 (7) | O2···C4iii | 3.161 (6) |
Br1···O1i | 3.426 (4) | O2···O1i | 2.840 (6) |
Br2···O1 | 3.232 (5) | O1···HO2iv | 2.25 (6) |
Br2···O2iii | 3.442 (4) | O2···H3iii | 2.7600 |
Br2···Br1iv | 3.6472 (7) | O2···H4iii | 2.6400 |
Br2···Br1v | 3.4762 (7) | C3···O2iii | 3.200 (6) |
Br2···Br4vi | 3.7961 (9) | C4···O2iii | 3.161 (6) |
Br3···O2 | 3.220 (4) | C5···Br1 | 3.729 (4) |
Br3···C9vi | 3.725 (5) | C9···Br3vii | 3.725 (5) |
Br4···O1 | 3.202 (5) | C6···HO2 | 2.90 (7) |
Br4···Br2vii | 3.7961 (9) | H1···Br4 | 2.8400 |
Br1···H7vii | 3.1700 | HO1···Br2 | 2.81 (9) |
Br1···H8viii | 3.1000 | HO1···Br1iv | 3.14 (9) |
Br1···HO2 | 2.98 (5) | HO1···HO2iv | 2.58 (10) |
Br1···HO1i | 3.14 (9) | HO2···Br1 | 2.98 (5) |
Br2···H8ix | 3.1900 | HO2···C6 | 2.90 (7) |
Br2···HO1 | 2.81 (9) | HO2···O1i | 2.25 (6) |
Br3···H3iii | 3.1900 | HO2···HO1i | 2.58 (10) |
Br3···H4 | 2.8300 | H3···Br3iii | 3.1900 |
Br4···H1 | 2.8400 | H3···O2iii | 2.7600 |
O1···Br2 | 3.232 (5) | H4···Br3 | 2.8300 |
O1···Br4 | 3.202 (5) | H4···O2iii | 2.6400 |
O1···Br1iv | 3.426 (4) | H7···Br1vi | 3.1700 |
O1···O2iv | 2.840 (6) | H8···Br1x | 3.1000 |
O2···Br2iii | 3.442 (4) | H8···Br2xi | 3.1900 |
| | | |
C1—O1—HO1 | 113 (8) | Br4—C9—C10 | 121.6 (4) |
C4—O2—HO2 | 101 (6) | C8—C9—C10 | 122.0 (5) |
O1—C1—C2 | 109.4 (4) | Br4—C9—C8 | 116.4 (4) |
O1—C1—C10 | 111.8 (4) | C5—C10—C9 | 119.2 (4) |
C2—C1—C10 | 114.6 (4) | C1—C10—C5 | 121.5 (4) |
Br1—C2—C1 | 108.1 (3) | C1—C10—C9 | 119.3 (4) |
C1—C2—C3 | 114.7 (4) | O1—C1—H1 | 107.00 |
Br1—C2—C3 | 107.0 (3) | C2—C1—H1 | 107.00 |
Br2—C3—C4 | 108.3 (3) | C10—C1—H1 | 107.00 |
Br2—C3—C2 | 107.0 (3) | Br1—C2—H2 | 109.00 |
C2—C3—C4 | 115.7 (4) | C1—C2—H2 | 109.00 |
O2—C4—C5 | 112.5 (4) | C3—C2—H2 | 109.00 |
O2—C4—C3 | 108.6 (4) | Br2—C3—H3 | 108.00 |
C3—C4—C5 | 113.6 (4) | C2—C3—H3 | 109.00 |
C6—C5—C10 | 117.6 (5) | C4—C3—H3 | 109.00 |
C4—C5—C10 | 123.8 (4) | O2—C4—H4 | 107.00 |
C4—C5—C6 | 118.7 (4) | C3—C4—H4 | 107.00 |
Br3—C6—C5 | 121.4 (4) | C5—C4—H4 | 107.00 |
Br3—C6—C7 | 116.2 (4) | C6—C7—H7 | 121.00 |
C5—C6—C7 | 122.4 (5) | C8—C7—H7 | 121.00 |
C6—C7—C8 | 118.9 (5) | C7—C8—H8 | 120.00 |
C7—C8—C9 | 120.0 (5) | C9—C8—H8 | 120.00 |
| | | |
C10—C1—C2—Br1 | −83.3 (4) | C3—C4—C5—C10 | −10.4 (6) |
C10—C1—C2—C3 | 35.9 (6) | C4—C5—C10—C9 | 179.1 (4) |
O1—C1—C2—C3 | −90.5 (5) | C4—C5—C6—Br3 | −1.2 (6) |
C2—C1—C10—C9 | 168.1 (4) | C4—C5—C6—C7 | −179.6 (5) |
O1—C1—C2—Br1 | 150.3 (3) | C6—C5—C10—C9 | 0.0 (7) |
O1—C1—C10—C5 | 113.0 (5) | C10—C5—C6—Br3 | 177.9 (3) |
O1—C1—C10—C9 | −66.7 (6) | C10—C5—C6—C7 | −0.4 (7) |
C2—C1—C10—C5 | −12.2 (6) | C4—C5—C10—C1 | −0.6 (7) |
C1—C2—C3—Br2 | 72.5 (5) | C6—C5—C10—C1 | −179.7 (4) |
Br1—C2—C3—Br2 | −167.7 (2) | C5—C6—C7—C8 | 0.7 (8) |
Br1—C2—C3—C4 | 71.5 (5) | Br3—C6—C7—C8 | −177.8 (5) |
C1—C2—C3—C4 | −48.3 (6) | C6—C7—C8—C9 | −0.5 (9) |
C2—C3—C4—O2 | −91.5 (5) | C7—C8—C9—C10 | 0.1 (9) |
Br2—C3—C4—C5 | −85.6 (4) | C7—C8—C9—Br4 | −179.7 (5) |
Br2—C3—C4—O2 | 148.4 (3) | Br4—C9—C10—C5 | 179.9 (4) |
C2—C3—C4—C5 | 34.5 (6) | Br4—C9—C10—C1 | −0.4 (6) |
C3—C4—C5—C6 | 168.7 (4) | C8—C9—C10—C5 | 0.1 (7) |
O2—C4—C5—C6 | −67.4 (5) | C8—C9—C10—C1 | 179.8 (5) |
O2—C4—C5—C10 | 113.5 (5) | | |
Symmetry codes: (i) x, −y+3/2, z+1/2; (ii) −x+2, y+1/2, −z+1/2; (iii) −x+2, −y+1, −z+1; (iv) x, −y+3/2, z−1/2; (v) −x+2, y−1/2, −z+1/2; (vi) −x+3/2, y−1/2, z; (vii) −x+3/2, y+1/2, z; (viii) x+1/2, −y+3/2, −z+1; (ix) x+1/2, y, −z+1/2; (x) x−1/2, −y+3/2, −z+1; (xi) x−1/2, y, −z+1/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—HO1···Br2 | 0.62 (7) | 2.81 (9) | 3.232 (5) | 130 (10) |
O2—HO2···O1i | 0.64 (6) | 2.25 (6) | 2.840 (6) | 155 (7) |
Symmetry code: (i) x, −y+3/2, z+1/2. |
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