organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 66| Part 4| April 2010| Pages o837-o838

1,4-Bis(hex­yl­oxy)-2,5-di­iodo­benzene

aInstitute of Chemistry, University of Neuchâtel, rue Emile-Argand 11, 2009 Neuchâtel, Switzerland, bXRD Application LAB, Microsystems Technology Division, Swiss Center for Electronics and Microtechnology, rue Jaquet Droz 1, CH-2001 Neuchâtel, Switzerland, and cInstitute of Physics, University of Neuchâtel, rue Emile-Argand 11, 2009 Neuchâtel, Switzerland
*Correspondence e-mail: reinhard.neier@unine.ch

(Received 19 January 2010; accepted 9 February 2010; online 13 March 2010)

The centrosymmetric title compound, C18H28I2O2, crystallized in the monoclinic space group P21/c with the alkyl chains having extended all-trans conformations, similar to those in the centrosymmetric bromo analogue [Li et al. (2008[Li, Y.-F., Xu, C., Cen, F.-F., Wang, Z.-Q. & Zhang, Y.-Q. (2008). Acta Cryst. E64, o1930.]). Acta Cryst. E64, o1930] that crystallized in the triclinic space group P[\overline{1}]. 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—Calk­yl—Calk­yl—Calk­yl 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 inter­actions. Instead, symmetry-related mol­ecules are linked via C—H⋯π contacts, forming a two-dimensional network.

Related literature

For use of the title compound in the synthesis of conjugated polymers, see: Van Heyningen et al. (2003[Van Heyningen, M. K., Verbiest, T., Persoons, A. & Samyn, C. (2003). PCT Int. Appl. WO, 2003003112, A1, 20030109.]); Mayor & Didschies (2003[Mayor, M. & Didschies, C. (2003). Angew. Chem. Int. Ed. 42, 3176-3179.]). For the various syntheses of the title compound, see: Castanet et al. (2002[Castanet, A. S., Colobert, F. & Broutin, P. E. (2002). Tetrahedron Lett. 43, 5047-5048.]); Van Heyningen et al. (2003[Van Heyningen, M. K., Verbiest, T., Persoons, A. & Samyn, C. (2003). PCT Int. Appl. WO, 2003003112, A1, 20030109.]); Mayor & Didschies (2003[Mayor, M. & Didschies, C. (2003). Angew. Chem. Int. Ed. 42, 3176-3179.]); Plater et al. (2004[Plater, M. J., Sinclair, J. P., Aiken, S., Gelbrich, T. & Hursthouse, M. B. (2004). Tetrahedron, 60, 6385-6394.]). For the synthesis and crystal structure of the bromo analogue, see: Maruyama & Kawanishi (2002[Maruyama, S. & Kawanishi, Y. (2002). J. Mater. Chem. 12, 2245-2249.]); Li et al. (2008[Li, Y.-F., Xu, C., Cen, F.-F., Wang, Z.-Q. & Zhang, Y.-Q. (2008). Acta Cryst. E64, o1930.]). For bond distances, see Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data
  • C18H28I2O2

  • Mr = 530.20

  • Monoclinic, P 21 /n

  • 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[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]) Tmin = 0.952, Tmax = 1.042

  • 7660 measured reflections

  • 1962 independent reflections

  • 1216 reflections with I > 2σ(I)

  • Rint = 0.058

Refinement
  • R[F2 > 2σ(F2)] = 0.029

  • wR(F2) = 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

Table 1
C—H⋯π inter­actions (Å, °)

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

D—H⋯centroid C—H H⋯Cg D⋯Cg C—H⋯Cg
C4′—H4′2⋯Cgii 0.99 2.74 3.595 (5) 145.0
Symmetry codes: (i) -x+1, -y+1, -z; (ii) [x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}.]

Data collection: EXPOSE in IPDS-I (Stoe & Cie, 2000[Stoe & Cie (2000). IPDS-I. Stoe & Cie GmbH, Darmstadt, Germany.]); cell refinement: CELL in IPDS-I; data reduction: INTEGRATE in IPDS-I; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: Mercury (Macrae et al., 2006[Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.]); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information


Comment top

The title compound has been used as a building block for the elaboration of organic–electronic materials, for example as a monomer for the synthesis of conjugated polymers (Van Heyningen et al., 2003; Mayor & Didschies, 2003). Our interest in this compound lies in the possibility of using it as a spacer-unit in linked materials for the creation of structured, discotic mesophases. The synthesis of the title compound has been reported by various groups (Van Heyningen et al., 2003; Mayor & Didschies, 2003; Plater et al., 2004). Here it was synthesized by iodination of 1,4-bis(hexyloxy)benzene (Castanet et al., 2002). The crystal structure of the bromo-analogue, synthesized by (Maruyama & Kawanishi, 2002), has been described by (Li et al., 2008).

The molecular structure of the title compound is illustrated in Fig. 1. Bond lengths are normal (Allen et al., 1987) and similar to those in the bromo-analogue (Li et al., 2008). The molecule possesses Ci symmetry with the inversion center situated at the center of the aromatic ring. The alkyl chains adopt a fully extended all-trans conformation. The C-atoms of the alkyl chain are almost coplanar (max. deviation of 0.052 (5) Å) and this mean plane is inclined to the benzene ring by 50.3 (3)°. In the bromo-analogue the alkyl chains also adopt a fully extended all-trans conformation. The alkyl C-atoms are also coplanar [max. deviation of 0.034 (4) Å] but here lie almost in the same plane as the aromatic ring, with a dihedral angle of 4.1 (2)°.

The different comformations of the two compounds are illustrated in Fig. 2. It can be seen that the alkyl chains are orientated differently with respect to the C(aromatic)—O bonds. The O1—C1'—C2'—C3' torsion angle is 55.8 (5)° in the title compound (Fig. 2b), while in the bromo-analogue this same angle is -179.1 (2)° (Fig. 2a). In the crystal structure of the title compound there are no halide···halide interactions, in contrast to the Br···Br interactions [3.410 (3) Å] observed in the bromo-analogue. However, symmetry related molecules are linked by C—H···π interactions leading to the formation of a two-dimensional network (Table 1 and Fig. 3; Cg is the centroid of the C1–C3/C1i–C3i benzene ring).

Related literature top

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 top

The title compound was synthesized by iodination of 1,4-bis(hexyloxy)benzene (Castanet et al., 2002). To a solution of 1,4-bis(hexyloxy)benzene (0.75 mmol) and N-iodosuccinimide (2.40 mmol) in dry acetonitrile (5.0 ml) was added trifluoroacetic acid (1.50 mmol) at RT. The mixture was heated and stirred at 363 K for 2 h. The reaction mixture was then cooled to RT and concentrated. Diethyl ether (30 ml) was added and the heterogeneous mixture was filtered to remove the white precipitate of succinimide that had formed. The organic layer was then washed with 10% NaHSO3 (aq) (3 × 30 ml) and dried over MgSO4. The crude product was purified by column chromatography [silica gel, Petroleum ether : CH2Cl2 (5:1)] and recrystallisation in methanol. Single crystals of the title compound were grown by slow evaporation of a concentrated solution in CH2Cl2 at RT. 1H NMR, 400 MHz (CDCl3) δ 7.17 (s, 2H, H3,3i), 3.93 (t, J = 6.6 Hz, 4H, H1'), 1.80 (quint, J = 6.6 Hz, 4H, H2'), 1.50 (m, 4H, H3'), 1.35 (m, 8H, H4',5'), 0.91 (t, J = 7.0 Hz, H6'); 13C NMR, 100 MHz (CDCl3) δ 152.8 (C2,2i), 122.7 (C3,3i), 86.3 (C1,1i), 70.3 (C1'), 31.4 (C5'), 29.1 (C2'), 25.7 (C3'), 22.6 (C4'), 14.0 (C6'); MS (EI): [M]+ = 529.95. The same numbering scheme has been used for the crystal structure.

Refinement top

The H-atoms could all be located in difference electron-density maps. In the final cycles of refinement they were included in calculated positions and treated as riding atoms: C—H = 0.98 - 0.99 Å, with Uiso(H) = k × Ueq(parent C-atom), where k = 1.2 for H-aromatic and H-methylene, and 1.5 for H-methyl.

Computing details top

Data collection: EXPOSE in IPDS-I (Stoe & Cie, 2000); cell refinement: CELL in IPDS-I (Stoe & Cie, 2000); data reduction: INTEGRATE in IPDS-I (Stoe & Cie, 2000); 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 & PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. A view of the molecular structure of the title compound, with displacement ellipoids drawn at the 50% probabilty level. Atoms labelled i are related to the other atoms by the symmetry operation -x+1, -y+1, -z.
[Figure 2] Fig. 2. A view of the different molecular conformations in (a) the bromo-analogue (Li et al., 2008), and (b) the title compound. The H-atoms have been omitted for clarity.
[Figure 3] Fig. 3. A view along the a-axis of the crystal packing in the title compound. The C—H···π interactions are illustrated by the H···C contacts [H4'2···C-atoms of the benzene ring] of 2.9–3.2 Å, drawn as dotted cyan lines. H-atoms not involved in the C—H···π interactions have been omitted for clarity; symmetry code (ii) -x+3/2, y-1/2, -z+1/2.
1,4-Bis(hexyloxy)-2,5-diiodobenzene top
Crystal data top
C18H28I2O2F(000) = 516
Mr = 530.20Dx = 1.767 Mg m3
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 mm1
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
Data collection top
STOE IPDS
diffractometer
1962 independent reflections
Radiation source: fine-focus sealed tube1216 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.058
ϕ rotation scansθmax = 26.1°, θmin = 2.6°
Absorption correction: multi-scan
MULscanABS in PLATON (Spek, 2009)
h = 1111
Tmin = 0.952, Tmax = 1.042k = 99
7660 measured reflectionsl = 1616
Refinement top
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 = 0.79 w = 1/[σ2(Fo2) + (0.0227P)2]
where P = (Fo2 + 2Fc2)/3
1962 reflections(Δ/σ)max < 0.001
101 parametersΔρmax = 0.81 e Å3
0 restraintsΔρmin = 1.31 e Å3
Crystal data top
C18H28I2O2V = 996.80 (16) Å3
Mr = 530.20Z = 2
Monoclinic, P21/nMo Kα radiation
a = 9.4481 (9) ŵ = 3.16 mm1
b = 7.8455 (6) ÅT = 173 K
c = 13.457 (2) Å0.32 × 0.11 × 0.06 mm
β = 92.148 (12)°
Data collection top
STOE IPDS
diffractometer
1962 independent reflections
Absorption correction: multi-scan
MULscanABS in PLATON (Spek, 2009)
1216 reflections with I > 2σ(I)
Tmin = 0.952, Tmax = 1.042Rint = 0.058
7660 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0290 restraints
wR(F2) = 0.055H-atom parameters constrained
S = 0.79Δρmax = 0.81 e Å3
1962 reflectionsΔρmin = 1.31 e Å3
101 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
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*
H30.531500.766900.076500.0210*
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*
Atomic displacement parameters (Å2) top
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)
Geometric parameters (Å, º) top
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—C2i0.2 (6)
C1'—O1—C1—C3i6.7 (6)O1—C1'—C2'—C3'55.8 (5)
C1—O1—C1'—C2'176.8 (4)I1—C2—C3—C1i179.5 (3)
O1—C1—C2—I11.5 (5)C1—C2—C3—C1i0.2 (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—C2i179.1 (4)
Symmetry codes: (i) x+1, y+1, z; (ii) x+5/2, y+1/2, z+1/2; (iii) x+3/2, y+1/2, z+1/2; (iv) x+2, y+1, z; (v) x1/2, y+1/2, z1/2; (vi) x+5/2, y1/2, z+1/2; (vii) x+3/2, y1/2, z+1/2; (viii) x+1/2, y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC18H28I2O2
Mr530.20
Crystal system, space groupMonoclinic, P21/n
Temperature (K)173
a, b, c (Å)9.4481 (9), 7.8455 (6), 13.457 (2)
β (°) 92.148 (12)
V3)996.80 (16)
Z2
Radiation typeMo Kα
µ (mm1)3.16
Crystal size (mm)0.32 × 0.11 × 0.06
Data collection
DiffractometerSTOE IPDS
diffractometer
Absorption correctionMulti-scan
MULscanABS in PLATON (Spek, 2009)
Tmin, Tmax0.952, 1.042
No. of measured, independent and
observed [I > 2σ(I)] reflections
7660, 1962, 1216
Rint0.058
(sin θ/λ)max1)0.618
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.029, 0.055, 0.79
No. of reflections1962
No. of parameters101
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.81, 1.31

Computer programs: EXPOSE in IPDS-I (Stoe & Cie, 2000), CELL in IPDS-I (Stoe & Cie, 2000), INTEGRATE in IPDS-I (Stoe & Cie, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), Mercury (Macrae et al., 2006), SHELXL97 & PLATON (Spek, 2009).

C—H···π interactions (Å, °) top
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) -x+1, -y+1, -z; (ii) -x+3/2, y-1/2, -z+1/2.
 

References

First citationAllen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.  CrossRef Web of Science Google Scholar
First citationCastanet, A. S., Colobert, F. & Broutin, P. E. (2002). Tetrahedron Lett. 43, 5047–5048.  Web of Science CrossRef CAS Google Scholar
First citationLi, Y.-F., Xu, C., Cen, F.-F., Wang, Z.-Q. & Zhang, Y.-Q. (2008). Acta Cryst. E64, o1930.  Web of Science CrossRef IUCr Journals Google Scholar
First citationMacrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453–457.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationMaruyama, S. & Kawanishi, Y. (2002). J. Mater. Chem. 12, 2245–2249.  Web of Science CrossRef CAS Google Scholar
First citationMayor, M. & Didschies, C. (2003). Angew. Chem. Int. Ed. 42, 3176–3179.  Web of Science CrossRef CAS Google Scholar
First citationPlater, M. J., Sinclair, J. P., Aiken, S., Gelbrich, T. & Hursthouse, M. B. (2004). Tetrahedron, 60, 6385–6394.  Web of Science CSD CrossRef CAS Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationStoe & Cie (2000). IPDS-I. Stoe & Cie GmbH, Darmstadt, Germany.  Google Scholar
First citationVan Heyningen, M. K., Verbiest, T., Persoons, A. & Samyn, C. (2003). PCT Int. Appl. WO, 2003003112, A1, 20030109.  Google Scholar

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Volume 66| Part 4| April 2010| Pages o837-o838
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