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4,4'-Di­iodo­bi­phenyl, C12H8I2, crystallizes as a homologous isomorph of the high-temperature form of p-di­iodo­benzene. The molecule is planar and lies on a center of symmetry. Each I atom is in contact with five others at distances between 4.0 and 4.5 Å.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804033331/ac6147sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804033331/ac6147Isup2.hkl
Contains datablock I

CCDC reference: 262492

Key indicators

  • Single-crystal X-ray study
  • T = 174 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.020
  • wR factor = 0.042
  • Data-to-parameter ratio = 20.1

checkCIF/PLATON results

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Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

4,4'-diiodobiphenyl top
Crystal data top
C12H8I2F(000) = 744
Mr = 405.98Dx = 2.374 Mg m3
Orthorhombic, PccnMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ab 2acCell parameters from 3990 reflections
a = 7.4189 (18) Åθ = 2.8–27.4°
b = 25.667 (6) ŵ = 5.49 mm1
c = 5.9653 (15) ÅT = 174 K
V = 1135.9 (5) Å3Prism, colorless
Z = 40.40 × 0.25 × 0.20 mm
Data collection top
Siemens SMART area-detector
diffractometer
1306 independent reflections
Radiation source: fine-focus sealed tube1233 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.026
ω scansθmax = 27.5°, θmin = 1.6°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996; Blessing, 1995)
h = 99
Tmin = 0.20, Tmax = 0.33k = 3333
12120 measured reflectionsl = 77
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)] = 0.020H-atom parameters constrained
wR(F2) = 0.042 w = 1/[σ2(Fo2) + (0.016P)2 + 0.834P]
where P = (Fo2 + 2Fc2)/3
S = 1.23(Δ/σ)max = 0.001
1306 reflectionsΔρmax = 0.41 e Å3
65 parametersΔρmin = 0.53 e Å3
0 restraintsExtinction correction: SHELXTL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0076 (2)
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
I10.47553 (2)0.697645 (6)0.08135 (3)0.03481 (9)
C10.4975 (3)0.52616 (9)0.4461 (3)0.0201 (4)
C20.5715 (3)0.57053 (9)0.5491 (4)0.0258 (5)
H20.62780.56690.69130.031*
C30.5651 (3)0.61934 (9)0.4501 (4)0.0288 (5)
H30.61530.64870.52440.035*
C40.4848 (3)0.62498 (9)0.2411 (4)0.0249 (4)
C50.4106 (3)0.58196 (9)0.1341 (4)0.0253 (5)
H50.35470.58580.00830.030*
C60.4181 (3)0.53347 (8)0.2353 (4)0.0230 (4)
H60.36800.50430.15970.028*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
I10.04208 (13)0.02253 (11)0.03984 (12)0.00278 (6)0.00090 (7)0.00474 (6)
C10.0162 (9)0.0228 (11)0.0214 (10)0.0008 (7)0.0009 (8)0.0016 (8)
C20.0275 (11)0.0270 (11)0.0229 (11)0.0031 (9)0.0052 (9)0.0025 (9)
C30.0301 (11)0.0269 (12)0.0294 (12)0.0044 (9)0.0037 (9)0.0052 (10)
C40.0238 (10)0.0225 (10)0.0285 (11)0.0025 (8)0.0038 (9)0.0004 (9)
C50.0246 (10)0.0272 (11)0.0242 (11)0.0028 (9)0.0020 (8)0.0002 (9)
C60.0225 (10)0.0233 (10)0.0233 (10)0.0002 (8)0.0012 (9)0.0043 (8)
Geometric parameters (Å, º) top
I1—C42.095 (2)C3—C41.389 (3)
C1—C21.406 (3)C3—H30.9500
C1—C61.401 (3)C4—C51.389 (3)
C1—C1i1.489 (4)C5—C61.385 (3)
C2—C31.386 (3)C5—H50.9500
C2—H20.9500C6—H60.9500
C2—C1—C6116.6 (2)C3—C4—C5120.0 (2)
C2—C1—C1i122.1 (2)C3—C4—I1120.97 (17)
C6—C1—C1i121.2 (2)C5—C4—I1119.05 (17)
C1—C2—C3122.2 (2)C6—C5—C4119.9 (2)
C1—C2—H2118.9C6—C5—H5120.1
C3—C2—H2118.9C4—C5—H5120.1
C4—C3—C2119.4 (2)C5—C6—C1121.9 (2)
C4—C3—H3120.3C5—C6—H6119.0
C2—C3—H3120.3C1—C6—H6119.0
Symmetry code: (i) x+1, y+1, z+1.
Distances and angles (Å, °) in C—I···I—C contacts in 4,4'diiodobiphenyl and p-diiodobenzene top
I'X—I···I'I···I'I···I'—XReference
Ii159.0 (2)4.015 (1)125.7 (2)a
Iii105.0 (2)4.015 (1)159.0 (2)a
Iiii125.7 (2)4.292 (1)125.7 (2)a
Iiv109.1 (2)4.483 (1)73.9 (2)a
Iv73.9 (2)4.483 (1)109.2 (2)a
I'164.24.10998.2b
I''98.24.109164.2b
I'''127.24.160127.2b
I''''116.04.40070.9b
I'''''70.94.400116.0b
References: (a) this work; (b) p-diiodobenzene (Boese & Miebach, 1996). Symmetry codes: (i) x, 3/2-y, -1/2+z; (ii) x, 3/2-y, 1/2+z; (iii) 1/2-x, 3/2-y, z; (iv) 1/2-x, y, -1/2+z; (v) 1/2-x, y, 1/2+z.
 

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