(1RS,2RS,3SR,4SR,9RS)-1,2,3,9-Tetra­bromo-1,2,3,4-tetra­hydro-1,4-methano­naphthalene

The title compound, C₁₁H₈Br₄, comprises a norbornane skeleton with four Br atoms, having a benzene ring fused on one side. The structure is stabilized by weak C—H...Br intra­molecular hydrogen-bonding inter­actions in addition to van der Waals forces.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.035
• wR factor = 0.089
• Data-to-parameter ratio = 16.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.97
PLAT030_ALERT_1_C _diffrn_reflns_number .LE.  _reflns_number_total          ?
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.80

Alert level G
ABSTM02_ALERT_3_G  When printed, the submitted absorption T values will be
            replaced by the scaled T values. Since the ratio of scaled T's
            is identical to the ratio of reported T values, the scaling
            does not imply a change to the absorption corrections used in
            the study.
            Ratio of Tmax expected/reported      0.802
            Tmax scaled      0.312 Tmin scaled      0.228

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   1 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
   2 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: COLLECT (Bruker, 2004); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: SCALEPACK and DENZO (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2003).

(1RS,2RS,3SR,4SR,9RS)-1,2,3,9-Tetrabromo-1,2,3,4-tetrahydro- 1,4-methanonaphthalene

Crystal data

C11H8Br4	F(000) = 856
Mr = 459.77	Dx = 2.462 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2168 reflections
a = 6.6220 (1) Å	θ = 2.2–68.3°
b = 13.6490 (3) Å	µ = 12.94 mm^−1
c = 13.7350 (3) Å	T = 294 K
β = 92.079 (1)°	Prism, colourless
V = 1240.60 (4) Å^3	0.13 × 0.10 × 0.09 mm
Z = 4

Data collection

Nonius KappaCCD diffractometer	2200 independent reflections
Horizonally mounted graphite crystal monochromator	2163 reflections with I > 2σ(I)
Detector resolution: 9 pixels mm^-1	Rint = 0.000
CCD scans	θmax = 25.3°, θmin = 2.1°
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	h = 0→7
Tmin = 0.284, Tmax = 0.389	k = 0→16
2200 measured reflections	l = −16→16

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)] = 0.035	H-atom parameters constrained
wR(F^2) = 0.089	w = 1/[σ^2(Fo^2) + (0.0436P)^2 + 1.8439P] where P = (Fo^2 + 2Fc^2)/3
S = 1.10	(Δ/σ)max = 0.001
2200 reflections	Δρmax = 0.68 e Å^−3
137 parameters	Δρmin = −0.64 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: 0.0193 (14)

Special details

Experimental. 13 C NMR (50 MHz, CDCl3): δ 142.6, 142.0, 131.5, 130.6, 127.5, 122.7, 71,7, 62.8, 62.5, 56.3, 53.6. IR (KBr, cm-1): ν 3055, 3030, 2979, 1447, 1421, 1396, 1294, 1268, 1242, 1165, 1140, 1012, 859.

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 (Ų)

	x	y	z	Uiso*/Ueq
Br1	0.92821 (7)	0.23070 (3)	0.53920 (3)	0.0464 (2)
Br2	0.92029 (7)	0.23801 (3)	0.84157 (3)	0.0421 (2)
Br3	0.43778 (7)	0.10350 (4)	0.83537 (3)	0.0525 (2)
Br4	0.43941 (6)	0.11631 (3)	0.57020 (3)	0.0411 (2)
C1	0.9261 (5)	−0.0217 (3)	0.7118 (3)	0.0317 (10)
C2	0.8455 (5)	0.0377 (3)	0.6273 (2)	0.0317 (10)
C3	0.9231 (6)	0.1422 (3)	0.6518 (2)	0.0302 (10)
C4	0.7788 (5)	0.1775 (2)	0.7304 (2)	0.0264 (9)
C5	0.6674 (5)	0.0822 (3)	0.7570 (2)	0.0287 (10)
C6	0.8192 (6)	0.0064 (2)	0.7932 (3)	0.0332 (10)
C7	0.6227 (5)	0.0394 (3)	0.6540 (2)	0.0298 (10)
C8	0.8600 (8)	−0.0332 (3)	0.8834 (3)	0.0475 (14)
C9	1.0176 (9)	−0.1020 (3)	0.8910 (4)	0.0571 (16)
C10	1.1242 (8)	−0.1294 (3)	0.8113 (4)	0.0536 (16)
C11	1.0815 (6)	−0.0902 (3)	0.7200 (3)	0.0428 (11)
H2	0.87420	0.01290	0.56230	0.0380*
H3	1.06000	0.13740	0.68100	0.0360*
H4	0.68170	0.22420	0.70140	0.0320*
H7	0.57190	−0.02780	0.65930	0.0360*
H8	0.78680	−0.01530	0.93720	0.0570*
H9	1.05070	−0.12970	0.95140	0.0690*
H10	1.22730	−0.17530	0.81900	0.0650*
H11	1.15380	−0.10890	0.66630	0.0510*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0546 (3)	0.0522 (3)	0.0328 (3)	−0.0001 (2)	0.0056 (2)	0.0137 (2)
Br2	0.0542 (3)	0.0390 (3)	0.0328 (3)	−0.0080 (2)	−0.0030 (2)	−0.0094 (2)
Br3	0.0512 (3)	0.0631 (3)	0.0446 (3)	−0.0122 (2)	0.0213 (2)	−0.0167 (2)
Br4	0.0396 (3)	0.0451 (3)	0.0380 (3)	0.0074 (2)	−0.0085 (2)	−0.0076 (2)
C1	0.0385 (19)	0.0258 (17)	0.0302 (18)	−0.0015 (13)	−0.0063 (14)	−0.0021 (14)
C2	0.0396 (19)	0.0331 (18)	0.0225 (17)	0.0074 (15)	0.0011 (14)	−0.0048 (14)
C3	0.0373 (18)	0.0319 (17)	0.0215 (16)	0.0039 (14)	0.0008 (13)	0.0044 (13)
C4	0.0304 (16)	0.0285 (16)	0.0200 (15)	0.0006 (13)	−0.0023 (13)	−0.0020 (12)
C5	0.0345 (17)	0.0338 (18)	0.0179 (15)	−0.0051 (14)	0.0029 (13)	−0.0049 (13)
C6	0.049 (2)	0.0246 (16)	0.0256 (17)	−0.0037 (15)	−0.0050 (15)	−0.0001 (13)
C7	0.0375 (18)	0.0282 (17)	0.0235 (16)	0.0030 (14)	−0.0021 (13)	−0.0052 (13)
C8	0.077 (3)	0.036 (2)	0.029 (2)	−0.016 (2)	−0.0063 (19)	0.0069 (16)
C9	0.086 (3)	0.033 (2)	0.050 (3)	−0.014 (2)	−0.031 (3)	0.0186 (19)
C10	0.068 (3)	0.029 (2)	0.062 (3)	0.0022 (19)	−0.023 (2)	0.0063 (19)
C11	0.046 (2)	0.0294 (19)	0.052 (2)	0.0030 (16)	−0.0105 (19)	−0.0019 (17)

Geometric parameters (Å, º)

Br1—C3	1.964 (3)	C6—C8	1.370 (6)
Br2—C4	1.946 (3)	C8—C9	1.405 (7)
Br3—C5	1.917 (3)	C9—C10	1.376 (8)
Br4—C7	1.949 (3)	C10—C11	1.383 (7)
C1—C2	1.498 (5)	C2—H2	0.9800
C1—C6	1.398 (6)	C3—H3	0.9800
C1—C11	1.392 (5)	C4—H4	0.9800
C2—C3	1.549 (6)	C7—H7	0.9800
C2—C7	1.533 (5)	C8—H8	0.9300
C3—C4	1.545 (5)	C9—H9	0.9300
C4—C5	1.546 (5)	C10—H10	0.9300
C5—C6	1.514 (5)	C11—H11	0.9300
C5—C7	1.549 (4)
Br1···Br4	3.6326 (6)	Br4···H3^v	3.0000
Br1···Br4^i	3.7382 (6)	Br4···H2^vii	3.2300
Br1···Br3^ii	3.6022 (6)	Br4···H4	2.7900
Br2···Br3^i	3.8913 (7)	C3···Br4^i	3.654 (4)
Br2···Br3	3.6834 (7)	C6···H3	2.8800
Br2···Br4^iii	3.7151 (6)	C9···H4^xi	2.9800
Br3···Br1^iv	3.6022 (6)	C9···H8^ix	3.1000
Br3···Br2	3.6834 (7)	C10···H4^xi	2.8500
Br3···Br2^v	3.8913 (7)	H2···Br4^vii	3.2300
Br3···Br4	3.6467 (6)	H2···H2^xii	2.4600
Br4···C3^v	3.654 (4)	H3···Br4^i	3.0000
Br4···Br2^vi	3.7151 (6)	H3···C6	2.8800
Br4···Br1	3.6326 (6)	H4···Br4	2.7900
Br4···Br4^vii	3.8152 (6)	H4···C9^x	2.9800
Br4···Br1^v	3.7382 (6)	H4···C10^x	2.8500
Br4···Br3	3.6467 (6)	H7···Br2^xi	3.2000
Br1···H10^viii	3.2100	H8···Br3	3.1100
Br2···H9^ix	3.2000	H8···C9^ix	3.1000
Br2···H7^x	3.2000	H9···Br2^ix	3.2000
Br3···H8	3.1100	H10···Br1^xiii	3.2100
C2—C1—C6	107.1 (3)	C6—C8—C9	116.9 (4)
C2—C1—C11	131.9 (4)	C8—C9—C10	121.6 (5)
C6—C1—C11	120.9 (4)	C9—C10—C11	121.5 (4)
C1—C2—C3	102.9 (3)	C1—C11—C10	117.4 (4)
C1—C2—C7	98.2 (3)	C1—C2—H2	116.00
C3—C2—C7	104.4 (3)	C3—C2—H2	116.00
Br1—C3—C2	114.23 (19)	C7—C2—H2	116.00
Br1—C3—C4	112.8 (2)	Br1—C3—H3	109.00
C2—C3—C4	103.3 (3)	C2—C3—H3	109.00
Br2—C4—C3	112.9 (2)	C4—C3—H3	109.00
Br2—C4—C5	113.08 (19)	Br2—C4—H4	109.00
C3—C4—C5	102.4 (3)	C3—C4—H4	109.00
Br3—C5—C4	113.6 (2)	C5—C4—H4	109.00
Br3—C5—C6	116.8 (2)	Br4—C7—H7	110.00
Br3—C5—C7	116.2 (2)	C2—C7—H7	110.00
C4—C5—C6	109.6 (3)	C5—C7—H7	110.00
C4—C5—C7	100.3 (2)	C6—C8—H8	122.00
C6—C5—C7	98.3 (3)	C9—C8—H8	122.00
C1—C6—C5	105.9 (3)	C8—C9—H9	119.00
C1—C6—C8	121.7 (4)	C10—C9—H9	119.00
C5—C6—C8	132.4 (4)	C9—C10—H10	119.00
Br4—C7—C2	116.8 (2)	C11—C10—H10	119.00
Br4—C7—C5	115.5 (3)	C1—C11—H11	121.00
C2—C7—C5	94.0 (2)	C10—C11—H11	121.00
C6—C1—C2—C3	70.0 (3)	Br2—C4—C5—C6	−62.9 (3)
C6—C1—C2—C7	−36.9 (4)	Br2—C4—C5—C7	−165.7 (2)
C11—C1—C2—C3	−107.1 (5)	C3—C4—C5—Br3	−168.6 (2)
C11—C1—C2—C7	146.0 (4)	C3—C4—C5—C6	58.8 (3)
C2—C1—C6—C5	1.5 (4)	C3—C4—C5—C7	−43.9 (3)
C2—C1—C6—C8	−178.6 (4)	Br3—C5—C6—C1	159.1 (3)
C11—C1—C6—C5	178.9 (3)	Br3—C5—C6—C8	−20.8 (6)
C11—C1—C6—C8	−1.2 (6)	C4—C5—C6—C1	−70.0 (3)
C2—C1—C11—C10	177.2 (4)	C4—C5—C6—C8	110.1 (4)
C6—C1—C11—C10	0.4 (6)	C7—C5—C6—C1	34.1 (3)
C1—C2—C3—Br1	160.0 (2)	C7—C5—C6—C8	−145.8 (4)
C1—C2—C3—C4	−77.1 (3)	Br3—C5—C7—Br4	58.0 (3)
C7—C2—C3—Br1	−97.9 (3)	Br3—C5—C7—C2	−179.7 (3)
C7—C2—C3—C4	25.0 (3)	C4—C5—C7—Br4	−64.9 (3)
C1—C2—C7—Br4	176.4 (3)	C4—C5—C7—C2	57.5 (3)
C1—C2—C7—C5	55.2 (3)	C6—C5—C7—Br4	−176.7 (2)
C3—C2—C7—Br4	70.7 (3)	C6—C5—C7—C2	−54.4 (3)
C3—C2—C7—C5	−50.5 (3)	C1—C6—C8—C9	1.4 (6)
Br1—C3—C4—Br2	−102.6 (2)	C5—C6—C8—C9	−178.8 (4)
Br1—C3—C4—C5	135.5 (2)	C6—C8—C9—C10	−0.9 (7)
C2—C3—C4—Br2	133.6 (2)	C8—C9—C10—C11	0.2 (7)
C2—C3—C4—C5	11.7 (3)	C9—C10—C11—C1	0.0 (7)
Br2—C4—C5—Br3	69.7 (3)

Symmetry codes: (i) x+1, y, z; (ii) x+1/2, −y+1/2, z−1/2; (iii) x+1/2, −y+1/2, z+1/2; (iv) x−1/2, −y+1/2, z+1/2; (v) x−1, y, z; (vi) x−1/2, −y+1/2, z−1/2; (vii) −x+1, −y, −z+1; (viii) −x+5/2, y+1/2, −z+3/2; (ix) −x+2, −y, −z+2; (x) −x+3/2, y+1/2, −z+3/2; (xi) −x+3/2, y−1/2, −z+3/2; (xii) −x+2, −y, −z+1; (xiii) −x+5/2, y−1/2, −z+3/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···Br4	0.98	2.79	3.199 (3)	106