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In the title compound, C11H8Br2, the crystal packing is dominated by inter­molecular Br...Br and C—H...π contacts.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807013669/cs2030sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807013669/cs2030Isup2.hkl
Contains datablock I

CCDC reference: 647171

Key indicators

  • Single-crystal X-ray study
  • T = 93 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.036
  • wR factor = 0.087
  • Data-to-parameter ratio = 50.0

checkCIF/PLATON results

No syntax errors found



Alert level B ABSTM02_ALERT_3_B The ratio of expected to reported Tmax/Tmin(RR') is < 0.75 Tmin and Tmax reported: 0.127 0.286 Tmin(prime) and Tmax expected: 0.112 0.189 RR(prime) = 0.748 Please check that your absorption correction is appropriate. PLAT061_ALERT_3_B Tmax/Tmin Range Test RR' too Large ............. 0.58
Alert level C PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.66 PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT153_ALERT_1_C The su's on the Cell Axes are Equal (x 100000) . 40 Ang. PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 300 Deg. PLAT230_ALERT_2_C Hirshfeld Test Diff for C2 - C3 .. 5.55 su PLAT764_ALERT_4_C Overcomplete CIF Bond List Detected (Rep/Expd) . 1.14 Ratio
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 0.659 Tmax scaled 0.189 Tmin scaled 0.084
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 2 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 3 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 2004); cell refinement: SMART; data reduction: SAINT (Bruker, 2004); 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: PLATON (Spek, 2003).

1-Bromo-2-(bromomethyl)naphthalene top
Crystal data top
C11H8Br2Z = 2
Mr = 299.99F(000) = 288
Triclinic, P1Dx = 2.063 Mg m3
a = 6.9074 (4) ÅMo Kα radiation, λ = 0.71073 Å
b = 8.3754 (4) ÅCell parameters from 6376 reflections
c = 8.5433 (4) Åθ = 3.0–36.3°
α = 92.054 (3)°µ = 8.34 mm1
β = 101.246 (3)°T = 93 K
γ = 94.013 (3)°Splinter, colourless
V = 482.95 (4) Å30.25 × 0.21 × 0.20 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
5954 independent reflections
Radiation source: fine-focus sealed tube4333 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.050
φ and ω scansθmax = 40.0°, θmin = 4.2°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2000)
h = 1212
Tmin = 0.127, Tmax = 0.286k = 1515
22317 measured reflectionsl = 1515
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.036H-atom parameters constrained
wR(F2) = 0.087 w = 1/[σ2(Fo2) + (0.0431P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max = 0.001
5954 reflectionsΔρmax = 1.67 e Å3
119 parametersΔρmin = 2.09 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0081 (15)
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
xyzUiso*/Ueq
Br10.69340 (2)0.28597 (2)0.70728 (2)0.01869 (5)
Br20.12009 (2)0.30078 (2)0.511045 (19)0.01678 (5)
C10.5267 (2)0.29026 (19)0.85968 (19)0.0136 (3)
C20.3543 (2)0.36586 (19)0.8260 (2)0.0153 (3)
C30.2303 (2)0.3663 (2)0.9413 (2)0.0175 (3)
H30.10940.41630.91880.021*
C40.2821 (2)0.2964 (2)1.0828 (2)0.0168 (3)
H40.19760.29901.15800.020*
C50.4612 (2)0.21916 (19)1.1199 (2)0.0145 (3)
C60.5166 (3)0.1476 (2)1.2673 (2)0.0176 (3)
H60.43210.14971.34260.021*
C70.6903 (3)0.0753 (2)1.3032 (2)0.0191 (3)
H70.72570.02781.40300.023*
C80.8167 (3)0.0713 (2)1.1926 (2)0.0192 (3)
H80.93700.02081.21800.023*
C90.7671 (2)0.1400 (2)1.0477 (2)0.0169 (3)
H90.85370.13650.97410.020*
C100.5879 (2)0.21609 (19)1.00702 (19)0.0136 (3)
C110.2902 (3)0.4491 (2)0.6746 (2)0.0189 (3)
H11A0.40820.48970.63410.023*
H11B0.21630.54180.69630.023*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.01644 (8)0.02554 (9)0.01503 (8)0.00065 (6)0.00580 (6)0.00088 (6)
Br20.01625 (7)0.01878 (8)0.01400 (8)0.00433 (5)0.00098 (5)0.00090 (6)
C10.0131 (6)0.0163 (6)0.0113 (6)0.0001 (5)0.0023 (5)0.0004 (5)
C20.0132 (6)0.0163 (6)0.0148 (7)0.0006 (5)0.0003 (5)0.0000 (5)
C30.0151 (6)0.0171 (7)0.0185 (7)0.0023 (5)0.0015 (5)0.0011 (6)
C40.0134 (6)0.0197 (7)0.0177 (7)0.0013 (5)0.0049 (5)0.0030 (6)
C50.0126 (6)0.0143 (6)0.0162 (7)0.0009 (5)0.0031 (5)0.0014 (5)
C60.0198 (7)0.0183 (7)0.0139 (7)0.0018 (5)0.0028 (5)0.0003 (6)
C70.0223 (7)0.0179 (7)0.0153 (7)0.0007 (6)0.0003 (6)0.0010 (6)
C80.0173 (7)0.0176 (7)0.0211 (8)0.0042 (5)0.0013 (6)0.0001 (6)
C90.0132 (6)0.0196 (7)0.0173 (7)0.0022 (5)0.0017 (5)0.0018 (6)
C100.0123 (6)0.0143 (6)0.0135 (6)0.0010 (5)0.0009 (5)0.0012 (5)
C110.0188 (7)0.0164 (7)0.0191 (8)0.0009 (5)0.0021 (6)0.0013 (6)
Geometric parameters (Å, º) top
Br1—C11.9001 (17)C5—C61.410 (2)
Br1—Br2i3.6611 (3)C5—C101.424 (2)
Br2—C111.9766 (17)C6—C71.369 (3)
Br2—Br1ii3.6611 (3)C6—H60.9500
C1—C21.374 (2)C7—C81.407 (3)
C1—C101.426 (2)C7—H70.9500
C2—C31.426 (3)C8—C91.376 (3)
C2—C111.496 (2)C8—H80.9500
C3—C41.357 (3)C9—C101.420 (2)
C3—H30.9500C9—H90.9500
C4—C51.422 (2)C11—H11A0.9900
C4—H40.9500C11—H11B0.9900
C1—Br1—Br2i164.36 (5)C5—C6—H6119.6
C11—Br2—Br1ii95.20 (6)C6—C7—C8120.15 (17)
C2—C1—C10122.36 (15)C6—C7—H7119.9
C2—C1—Br1119.44 (13)C8—C7—H7119.9
C10—C1—Br1118.20 (12)C9—C8—C7120.42 (16)
C1—C2—C3118.54 (15)C9—C8—H8119.8
C1—C2—C11123.33 (16)C7—C8—H8119.8
C3—C2—C11118.13 (15)C8—C9—C10120.79 (16)
C4—C3—C2121.11 (15)C8—C9—H9119.6
C4—C3—H3119.4C10—C9—H9119.6
C2—C3—H3119.4C9—C10—C5118.24 (15)
C3—C4—C5120.94 (16)C9—C10—C1124.05 (16)
C3—C4—H4119.5C5—C10—C1117.71 (14)
C5—C4—H4119.5C2—C11—Br2110.62 (11)
C6—C5—C4121.13 (16)C2—C11—H11A109.5
C6—C5—C10119.53 (15)Br2—C11—H11A109.5
C4—C5—C10119.33 (16)C2—C11—H11B109.5
C7—C6—C5120.88 (17)Br2—C11—H11B109.5
C7—C6—H6119.6H11A—C11—H11B108.1
Br2i—Br1—C1—C2137.78 (14)C7—C8—C9—C100.0 (2)
Br2i—Br1—C1—C1041.3 (3)C8—C9—C10—C50.1 (2)
C10—C1—C2—C31.6 (2)C8—C9—C10—C1179.82 (15)
Br1—C1—C2—C3179.36 (11)C6—C5—C10—C90.1 (2)
C10—C1—C2—C11177.95 (14)C4—C5—C10—C9179.23 (14)
Br1—C1—C2—C111.1 (2)C6—C5—C10—C1179.81 (14)
C1—C2—C3—C41.2 (2)C4—C5—C10—C10.7 (2)
C11—C2—C3—C4178.39 (15)C2—C1—C10—C9178.51 (15)
C2—C3—C4—C50.6 (2)Br1—C1—C10—C90.5 (2)
C3—C4—C5—C6179.42 (16)C2—C1—C10—C51.4 (2)
C3—C4—C5—C100.3 (2)Br1—C1—C10—C5179.61 (11)
C4—C5—C6—C7179.14 (15)C1—C2—C11—Br291.78 (17)
C10—C5—C6—C70.0 (2)C3—C2—C11—Br288.64 (16)
C5—C6—C7—C80.1 (3)Br1ii—Br2—C11—C271.37 (13)
C6—C7—C8—C90.1 (3)
Symmetry codes: (i) x+1, y, z; (ii) x1, y, z.
 

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