trans,trans,trans-2,3,5,8-Tetra­bromo-1,4-di­hydroxy-1,2,3,4-tetra­hydro­naphthalene

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 Q_T of 0.386 (5) Å. The crystal structure is stabilized by short inter- and intramolecular hydrogen-bond contacts.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](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

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Computing details

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

Crystal data

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) Å^3	Plate, colorless
Z = 8	0.64 × 0.41 × 0.12 mm

Data collection

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

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.082	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0198P)^2 + 5.027P] where P = (Fo^2 + 2Fc^2)/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

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 F^{2 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 F}2, conventional R-factors R are based on F, with F set to zero for negative F^{2. The observed criterion of F}2 > σ(F^{2) is used only for calculating -R-factor-obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F}2 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	0.97279 (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 (Ų)

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

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···Br2^i	3.6472 (7)	O2···C3^iii	3.200 (6)
Br1···Br2^ii	3.4762 (7)	O2···C4^iii	3.161 (6)
Br1···O1^i	3.426 (4)	O2···O1^i	2.840 (6)
Br2···O1	3.232 (5)	O1···HO2^iv	2.25 (6)
Br2···O2^iii	3.442 (4)	O2···H3^iii	2.7600
Br2···Br1^iv	3.6472 (7)	O2···H4^iii	2.6400
Br2···Br1^v	3.4762 (7)	C3···O2^iii	3.200 (6)
Br2···Br4^vi	3.7961 (9)	C4···O2^iii	3.161 (6)
Br3···O2	3.220 (4)	C5···Br1	3.729 (4)
Br3···C9^vi	3.725 (5)	C9···Br3^vii	3.725 (5)
Br4···O1	3.202 (5)	C6···HO2	2.90 (7)
Br4···Br2^vii	3.7961 (9)	H1···Br4	2.8400
Br1···H7^vii	3.1700	HO1···Br2	2.81 (9)
Br1···H8^viii	3.1000	HO1···Br1^iv	3.14 (9)
Br1···HO2	2.98 (5)	HO1···HO2^iv	2.58 (10)
Br1···HO1^i	3.14 (9)	HO2···Br1	2.98 (5)
Br2···H8^ix	3.1900	HO2···C6	2.90 (7)
Br2···HO1	2.81 (9)	HO2···O1^i	2.25 (6)
Br3···H3^iii	3.1900	HO2···HO1^i	2.58 (10)
Br3···H4	2.8300	H3···Br3^iii	3.1900
Br4···H1	2.8400	H3···O2^iii	2.7600
O1···Br2	3.232 (5)	H4···Br3	2.8300
O1···Br4	3.202 (5)	H4···O2^iii	2.6400
O1···Br1^iv	3.426 (4)	H7···Br1^vi	3.1700
O1···O2^iv	2.840 (6)	H8···Br1^x	3.1000
O2···Br2^iii	3.442 (4)	H8···Br2^xi	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)

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···O1^i	0.64 (6)	2.25 (6)	2.840 (6)	155 (7)

Symmetry code: (i) x, −y+3/2, z+1/2.