Literature DB >> 21580664

1,4-Bis(hex-yloxy)-2,5-diiodo-benzene.

Damien Thevenet, Reinhard Neier, Olha Sereda, Antonia Neels, Helen Stoeckli-Evans.   

Abstract

The centrosymmetric title compound, C(18)H(28)I(2)O(2), crystallized in the monoclinic space group P2(1)/c with the alkyl chains having extended all-trans conformations, similar to those in the centrosymmetric bromo analogue [Li et al. (2008 ▶). Acta Cryst. E64, o1930] that crystallized in the triclinic space group P. The difference between the two structures lies in the orientation of the two alkyl chains with respect to the C(aromatic)-O bond. In the title compound, the O-C(alk-yl)-C(alk-yl)-C(alk-yl) torsion angle is 55.8 (5)°, while in the bromo analogue this angle is -179.1 (2)°. In the title compound, the C-atoms of the alkyl chain are almost coplanar [maximum deviation of 0.052 (5) Å] and this mean plane is inclined to the benzene ring by 50.3 (3)°. In the bromo-analogue, these two mean planes are almost coplanar, making a dihedral angle of 4.1 (2)°. Another difference between the crystal structures of the two compounds is that in the title compound there are no halide⋯halide inter-actions. Instead, symmetry-related mol-ecules are linked via C-H⋯π contacts, forming a two-dimensional network.

Entities:  

Year:  2010        PMID： 21580664      PMCID： PMC2983920          DOI： 10.1107/S1600536810005258

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For use of the title compound in the synthesis of conjugated polymers, see: Van Heyningen et al. (2003 ▶); Mayor & Didschies (2003 ▶). For the various syntheses of the title compound, see: Castanet et al. (2002 ▶); Van Heyningen et al. (2003 ▶); Mayor & Didschies (2003 ▶); Plater et al. (2004 ▶). For the synthesis and crystal structure of the bromo analogue, see: Maruyama & Kawanishi (2002 ▶); Li et al. (2008 ▶). For bond distances, see Allen et al. (1987 ▶).

Experimental

Crystal data

C18H28I2O2 M = 530.20 Monoclinic, a = 9.4481 (9) Å b = 7.8455 (6) Å c = 13.457 (2) Å β = 92.148 (12)° V = 996.80 (16) Å3 Z = 2 Mo Kα radiation μ = 3.16 mm−1 T = 173 K 0.32 × 0.11 × 0.06 mm

Data collection

STOE IPDS diffractometer Absorption correction: multi-scan MULscanABS in PLATON (Spek, 2009 ▶) T min = 0.952, T max = 1.042 7660 measured reflections 1962 independent reflections 1216 reflections with I > 2σ(I) R int = 0.058

Refinement

R[F 2 > 2σ(F 2)] = 0.029 wR(F 2) = 0.055 S = 0.79 1962 reflections 101 parameters H-atom parameters constrained Δρmax = 0.81 e Å−3 Δρmin = −1.31 e Å−3 Data collection: EXPOSE in IPDS-I (Stoe & Cie, 2000 ▶); cell refinement: CELL in IPDS-I; data reduction: INTEGRATE in IPDS-I; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶). Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810005258/lx2134sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536810005258/lx2134Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C18H28I2O2F(000) = 516
Mr = 530.20Dx = 1.767 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 7553 reflections
a = 9.4481 (9) Åθ = 0.9–26.3°
b = 7.8455 (6) ŵ = 3.16 mm−1
c = 13.457 (2) ÅT = 173 K
β = 92.148 (12)°Rod, colorless
V = 996.80 (16) Å30.32 × 0.11 × 0.06 mm
Z = 2
STOE IPDS diffractometer1962 independent reflections
Radiation source: fine-focus sealed tube1216 reflections with I > 2σ(I)
graphiteRint = 0.058
φ rotation scansθmax = 26.1°, θmin = 2.6°
Absorption correction: multi-scan MULscanABS in PLATON (Spek, 2009)h = −11→11
Tmin = 0.952, Tmax = 1.042k = −9→9
7660 measured reflectionsl = −16→16
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.029Hydrogen site location: difference Fourier map
wR(F2) = 0.055H-atom parameters constrained
S = 0.79w = 1/[σ2(Fo2) + (0.0227P)2] where P = (Fo2 + 2Fc2)/3
1962 reflections(Δ/σ)max < 0.001
101 parametersΔρmax = 0.81 e Å−3
0 restraintsΔρmin = −1.31 e Å−3
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 esds are taken into account in the estimation of distances, angles and torsion angles
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.
xyzUiso*/Ueq
I10.82998 (3)0.69287 (4)0.01561 (3)0.0307 (1)
O10.7295 (3)0.3497 (4)0.0975 (2)0.0276 (10)
C10.6122 (4)0.4192 (6)0.0508 (3)0.0215 (14)
C1'0.7158 (4)0.1961 (7)0.1533 (3)0.0279 (16)
C20.6307 (4)0.5768 (6)0.0054 (3)0.0214 (16)
C2'0.8638 (5)0.1475 (6)0.1902 (4)0.0286 (16)
C30.5180 (4)0.6593 (6)−0.0459 (3)0.0170 (14)
C3'0.9402 (4)0.2857 (6)0.2498 (3)0.0242 (16)
C4'1.0897 (5)0.2350 (6)0.2818 (3)0.0261 (16)
C5'1.1699 (5)0.3737 (6)0.3398 (4)0.0332 (17)
C6'1.3227 (5)0.3225 (8)0.3657 (4)0.0373 (16)
H1'10.674200.104600.110800.0340*
H1'20.653900.214700.210100.0340*
H30.531500.76690−0.076500.0210*
H2'10.920600.118400.132200.0340*
H2'20.857800.044200.232100.0340*
H3'10.943500.390700.209200.0290*
H3'20.886200.311500.309600.0290*
H4'11.142700.206100.221900.0310*
H4'21.085900.131400.323500.0310*
H5'11.120500.397900.401800.0400*
H5'21.169600.479500.299700.0400*
H6'11.323500.216000.403800.0560*
H6'21.368800.412600.405700.0560*
H6'31.373800.306100.304400.0560*
U11U22U33U12U13U23
I10.0231 (1)0.0311 (2)0.0374 (2)−0.0054 (2)−0.0051 (1)0.0055 (2)
O10.0202 (14)0.026 (2)0.0358 (19)−0.0003 (12)−0.0093 (13)0.0145 (15)
C10.019 (2)0.021 (3)0.024 (2)0.0025 (18)−0.0054 (18)−0.001 (2)
C1'0.028 (2)0.021 (3)0.034 (3)−0.003 (2)−0.0063 (19)0.007 (3)
C20.021 (2)0.023 (3)0.020 (3)−0.0020 (18)−0.0013 (17)−0.003 (2)
C2'0.029 (2)0.025 (3)0.031 (3)0.001 (2)−0.008 (2)0.005 (2)
C30.0108 (19)0.022 (3)0.018 (2)−0.0001 (18)−0.0003 (16)−0.001 (2)
C3'0.022 (2)0.023 (3)0.027 (3)0.002 (2)−0.0054 (18)0.004 (2)
C4'0.028 (2)0.026 (3)0.024 (3)0.0020 (18)−0.004 (2)0.006 (2)
C5'0.031 (3)0.025 (3)0.043 (3)−0.001 (2)−0.007 (2)0.008 (2)
C6'0.027 (2)0.039 (3)0.045 (3)−0.006 (3)−0.010 (2)0.002 (3)
I1—C22.091 (4)C2'—H2'10.9900
O1—C11.367 (5)C2'—H2'20.9900
O1—C1'1.428 (6)C3—H30.9500
C1—C21.393 (6)C3'—H3'10.9900
C1—C3i1.375 (6)C3'—H3'20.9900
C1'—C2'1.515 (6)C4'—H4'10.9900
C2—C31.405 (6)C4'—H4'20.9900
C2'—C3'1.515 (7)C5'—H5'10.9900
C3'—C4'1.514 (6)C5'—H5'20.9900
C4'—C5'1.524 (7)C6'—H6'10.9800
C5'—C6'1.526 (7)C6'—H6'20.9800
C1'—H1'10.9900C6'—H6'30.9800
C1'—H1'20.9900
I1···O13.073 (3)H2'1···H4'12.4800
I1···C6'ii3.736 (5)H2'2···H4'22.5400
I1···H3'2iii3.3100H2'2···O1vii2.9000
I1···H4'1iv3.3100H2'2···C1vii3.0800
O1···I13.073 (3)H3'1···O12.4900
O1···H3'12.4900H3'1···H5'22.5200
O1···H2'2iii2.9000H3'2···H5'12.5900
O1···H6'1v2.8300H3'2···I1vii3.3100
C6'···I1vi3.736 (5)H4'1···H2'12.4800
C1···H4'2iii3.0600H4'1···H6'32.5400
C1···H4'2v3.0900H4'1···H5'2vi2.5400
C1···H2'2iii3.0800H4'1···I1iv3.3100
C1···H6'1v3.0500H4'2···H2'22.5400
C1'···H3i2.5400H4'2···H6'12.5400
C2···H4'2v2.9600H4'2···C1vii3.0600
C3···H5'1iii3.0300H4'2···C1viii3.0900
C3···H1'2i2.8700H4'2···C2viii2.9600
C3···H4'2v2.9600H4'2···C3viii2.9600
C3···H1'1i2.7200H5'1···H3'22.5900
H1'1···C3i2.7200H5'1···C3vii3.0300
H1'1···H3i2.2200H5'2···H3'12.5200
H1'2···C3i2.8700H5'2···H4'1ii2.5400
H1'2···H3i2.4700H6'1···H4'22.5400
H3···C1'i2.5400H6'1···O1viii2.8300
H3···H1'1i2.2200H6'1···C1viii3.0500
H3···H1'2i2.4700H6'3···H4'12.5400
C1—O1—C1'119.4 (3)C2—C3—H3121.00
O1—C1—C2116.3 (3)C1i—C3—H3121.00
O1—C1—C3i123.5 (4)C2'—C3'—H3'1109.00
C2—C1—C3i120.2 (4)C2'—C3'—H3'2109.00
O1—C1'—C2'106.5 (3)C4'—C3'—H3'1109.00
I1—C2—C1119.0 (3)C4'—C3'—H3'2109.00
I1—C2—C3119.7 (3)H3'1—C3'—H3'2108.00
C1—C2—C3121.3 (4)C3'—C4'—H4'1109.00
C1'—C2'—C3'114.1 (4)C3'—C4'—H4'2109.00
C1i—C3—C2118.5 (4)C5'—C4'—H4'1109.00
C2'—C3'—C4'112.5 (4)C5'—C4'—H4'2109.00
C3'—C4'—C5'113.5 (4)H4'1—C4'—H4'2108.00
C4'—C5'—C6'112.1 (4)C4'—C5'—H5'1109.00
O1—C1'—H1'1110.00C4'—C5'—H5'2109.00
O1—C1'—H1'2110.00C6'—C5'—H5'1109.00
C2'—C1'—H1'1110.00C6'—C5'—H5'2109.00
C2'—C1'—H1'2110.00H5'1—C5'—H5'2108.00
H1'1—C1'—H1'2109.00C5'—C6'—H6'1109.00
C1'—C2'—H2'1109.00C5'—C6'—H6'2109.00
C1'—C2'—H2'2109.00C5'—C6'—H6'3110.00
C3'—C2'—H2'1109.00H6'1—C6'—H6'2109.00
C3'—C2'—H2'2109.00H6'1—C6'—H6'3110.00
H2'1—C2'—H2'2108.00H6'2—C6'—H6'3110.00
C1'—O1—C1—C2174.3 (4)C2—C1—C3i—C2i−0.2 (6)
C1'—O1—C1—C3i−6.7 (6)O1—C1'—C2'—C3'55.8 (5)
C1—O1—C1'—C2'176.8 (4)I1—C2—C3—C1i−179.5 (3)
O1—C1—C2—I1−1.5 (5)C1—C2—C3—C1i−0.2 (6)
O1—C1—C2—C3179.2 (4)C1'—C2'—C3'—C4'−177.7 (4)
C3i—C1—C2—I1179.5 (3)C2'—C3'—C4'—C5'178.6 (4)
C3i—C1—C2—C30.2 (6)C3'—C4'—C5'—C6'−176.7 (4)
O1—C1—C3i—C2i−179.1 (4)
D—H···centroidC—HH···CgD···CgC—H···Cg
C4'—H4'2···Cgii0.992.743.595 (5)145.0
Table 1

C—H⋯π inter­actions (Å, °)

Cg1 is the centroid of the C1–C3/C1i–C3i ring.

D—H⋯centroidC—HH⋯CgD⋯CgC—H⋯Cg
C4′—H4′2⋯Cgii0.992.743.595 (5)145.0

Symmetry codes: (i) ; (ii)

  4 in total

1.  A giant conjugated molecular ring.

Authors:  Marcel Mayor; Claudia Didschies
Journal:  Angew Chem Int Ed Engl       Date:  2003-07-14       Impact factor: 15.336

2.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

3.  1,4-Dibromo-2,5-bis-(hex-yloxy)benzene.

Authors:  Ying-Fei Li; Chen Xu; Fei-Fei Cen; Zhi-Qiang Wang; Yu-Qing Zhang
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2008-09-13

4.  Structure validation in chemical crystallography.

Authors:  Anthony L Spek
Journal:  Acta Crystallogr D Biol Crystallogr       Date:  2009-01-20
  4 in total
  1 in total

1.  1,4-Bis(hex-yloxy)benzene.

Authors:  Hua Cheng
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2013-10-31
  1 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.