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
CCDC reference: 262492
Key indicators
- Single-crystal X-ray study
- T = 174 K
- Mean (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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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.
Crystal data top
C12H8I2 | F(000) = 744 |
Mr = 405.98 | Dx = 2.374 Mg m−3 |
Orthorhombic, Pccn | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ab 2ac | Cell parameters from 3990 reflections |
a = 7.4189 (18) Å | θ = 2.8–27.4° |
b = 25.667 (6) Å | µ = 5.49 mm−1 |
c = 5.9653 (15) Å | T = 174 K |
V = 1135.9 (5) Å3 | Prism, colorless |
Z = 4 | 0.40 × 0.25 × 0.20 mm |
Data collection top
Siemens SMART area-detector diffractometer | 1306 independent reflections |
Radiation source: fine-focus sealed tube | 1233 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.026 |
ω scans | θmax = 27.5°, θmin = 1.6° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996; Blessing, 1995) | h = −9→9 |
Tmin = 0.20, Tmax = 0.33 | k = −33→33 |
12120 measured reflections | l = −7→7 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.020 | H-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 reflections | Δρmax = 0.41 e Å−3 |
65 parameters | Δρmin = −0.53 e Å−3 |
0 restraints | Extinction correction: SHELXTL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0076 (2) |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
I1 | 0.47553 (2) | 0.697645 (6) | 0.08135 (3) | 0.03481 (9) | |
C1 | 0.4975 (3) | 0.52616 (9) | 0.4461 (3) | 0.0201 (4) | |
C2 | 0.5715 (3) | 0.57053 (9) | 0.5491 (4) | 0.0258 (5) | |
H2 | 0.6278 | 0.5669 | 0.6913 | 0.031* | |
C3 | 0.5651 (3) | 0.61934 (9) | 0.4501 (4) | 0.0288 (5) | |
H3 | 0.6153 | 0.6487 | 0.5244 | 0.035* | |
C4 | 0.4848 (3) | 0.62498 (9) | 0.2411 (4) | 0.0249 (4) | |
C5 | 0.4106 (3) | 0.58196 (9) | 0.1341 (4) | 0.0253 (5) | |
H5 | 0.3547 | 0.5858 | −0.0083 | 0.030* | |
C6 | 0.4181 (3) | 0.53347 (8) | 0.2353 (4) | 0.0230 (4) | |
H6 | 0.3680 | 0.5043 | 0.1597 | 0.028* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
I1 | 0.04208 (13) | 0.02253 (11) | 0.03984 (12) | 0.00278 (6) | −0.00090 (7) | 0.00474 (6) |
C1 | 0.0162 (9) | 0.0228 (11) | 0.0214 (10) | 0.0008 (7) | 0.0009 (8) | −0.0016 (8) |
C2 | 0.0275 (11) | 0.0270 (11) | 0.0229 (11) | −0.0031 (9) | −0.0052 (9) | −0.0025 (9) |
C3 | 0.0301 (11) | 0.0269 (12) | 0.0294 (12) | −0.0044 (9) | −0.0037 (9) | −0.0052 (10) |
C4 | 0.0238 (10) | 0.0225 (10) | 0.0285 (11) | 0.0025 (8) | 0.0038 (9) | −0.0004 (9) |
C5 | 0.0246 (10) | 0.0272 (11) | 0.0242 (11) | 0.0028 (9) | −0.0020 (8) | −0.0002 (9) |
C6 | 0.0225 (10) | 0.0233 (10) | 0.0233 (10) | −0.0002 (8) | −0.0012 (9) | −0.0043 (8) |
Geometric parameters (Å, º) top
I1—C4 | 2.095 (2) | C3—C4 | 1.389 (3) |
C1—C2 | 1.406 (3) | C3—H3 | 0.9500 |
C1—C6 | 1.401 (3) | C4—C5 | 1.389 (3) |
C1—C1i | 1.489 (4) | C5—C6 | 1.385 (3) |
C2—C3 | 1.386 (3) | C5—H5 | 0.9500 |
C2—H2 | 0.9500 | C6—H6 | 0.9500 |
| | | |
C2—C1—C6 | 116.6 (2) | C3—C4—C5 | 120.0 (2) |
C2—C1—C1i | 122.1 (2) | C3—C4—I1 | 120.97 (17) |
C6—C1—C1i | 121.2 (2) | C5—C4—I1 | 119.05 (17) |
C1—C2—C3 | 122.2 (2) | C6—C5—C4 | 119.9 (2) |
C1—C2—H2 | 118.9 | C6—C5—H5 | 120.1 |
C3—C2—H2 | 118.9 | C4—C5—H5 | 120.1 |
C4—C3—C2 | 119.4 (2) | C5—C6—C1 | 121.9 (2) |
C4—C3—H3 | 120.3 | C5—C6—H6 | 119.0 |
C2—C3—H3 | 120.3 | C1—C6—H6 | 119.0 |
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 topI' | X—I···I' | I···I' | I···I'—X | Reference |
Ii | 159.0 (2) | 4.015 (1) | 125.7 (2) | a |
Iii | 105.0 (2) | 4.015 (1) | 159.0 (2) | a |
Iiii | 125.7 (2) | 4.292 (1) | 125.7 (2) | a |
Iiv | 109.1 (2) | 4.483 (1) | 73.9 (2) | a |
Iv | 73.9 (2) | 4.483 (1) | 109.2 (2) | a |
I' | 164.2 | 4.109 | 98.2 | b |
I'' | 98.2 | 4.109 | 164.2 | b |
I''' | 127.2 | 4.160 | 127.2 | b |
I'''' | 116.0 | 4.400 | 70.9 | b |
I''''' | 70.9 | 4.400 | 116.0 | b |
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. |