1,4-Bis(hex­yloxy)-2,5-diiodo­benzene

Thevenet, D.; Neier, R.; Sereda, O.; Neels, A.; Stoeckli-Evans, H.

doi:10.1107/S1600536810005258

organic compounds

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ISSN: 2056-9890

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

doi:10.1107/S1600536810005258

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

Damien Thevenet,^a Reinhard Neier,^a Olha Sereda,^b Antonia Neels ^b and Helen Stoeckli-Evans ^c ^*

^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 ). 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—C_alkyl—C_alkyl—C_alkyl 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 ); 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_r = 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 ) 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[F² > 2σ(F²)] = 0.029
wR(F²) = 0.055
S = 0.79
1962 reflections
101 parameters
H-atom parameters constrained
Δρ_max = 0.81 e Å⁻³
Δρ_min = −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 ); 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).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810005258/lx2134sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810005258/lx2134Isup2.hkl

checkCIF report

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 C_i 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, H_3,3ⁱ), 3.93 (t, J = 6.6 Hz, 4H, H_1'), 1.80 (quint, J = 6.6 Hz, 4H, H_2'), 1.50 (m, 4H, H_3'), 1.35 (m, 8H, H_4',5'), 0.91 (t, J = 7.0 Hz, H_6'); ¹³C NMR, 100 MHz (CDCl₃) δ 152.8 (C_2,2ⁱ), 122.7 (C_3,3ⁱ), 86.3 (C_1,1ⁱ), 70.3 (C_1'), 31.4 (C_5'), 29.1 (C_2'), 25.7 (C_3'), 22.6 (C_4'), 14.0 (C_6'); MS (EI): [M]⁺ = 529.95. The same numbering scheme has been used for the crystal structure.

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

	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.
	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.
	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

C₁₈H₂₈I₂O₂	F(000) = 516
M_r = 530.20	D_x = 1.767 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 7553 reflections
a = 9.4481 (9) Å	θ = 0.9–26.3°
b = 7.8455 (6) Å	µ = 3.16 mm⁻¹
c = 13.457 (2) Å	T = 173 K
β = 92.148 (12)°	Rod, colorless
V = 996.80 (16) Å³	0.32 × 0.11 × 0.06 mm
Z = 2

Data collection top

STOE IPDS diffractometer	1962 independent reflections
Radiation source: fine-focus sealed tube	1216 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.058
ϕ rotation scans	θ_max = 26.1°, θ_min = 2.6°
Absorption correction: multi-scan MULscanABS in PLATON (Spek, 2009)	h = −11→11
T_min = 0.952, T_max = 1.042	k = −9→9
7660 measured reflections	l = −16→16

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.029	Hydrogen site location: difference Fourier map
wR(F²) = 0.055	H-atom parameters constrained
S = 0.79	w = 1/[σ²(F_o²) + (0.0227P)²] where P = (F_o² + 2F_c²)/3
1962 reflections	(Δ/σ)_max < 0.001
101 parameters	Δρ_max = 0.81 e Å⁻³
0 restraints	Δρ_min = −1.31 e Å⁻³

Crystal data top

C₁₈H₂₈I₂O₂	V = 996.80 (16) Å³
M_r = 530.20	Z = 2
Monoclinic, P2₁/n	Mo Kα radiation
a = 9.4481 (9) Å	µ = 3.16 mm⁻¹
b = 7.8455 (6) Å	T = 173 K
c = 13.457 (2) Å	0.32 × 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)
T_min = 0.952, T_max = 1.042	R_int = 0.058
7660 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.029	0 restraints
wR(F²) = 0.055	H-atom parameters constrained
S = 0.79	Δρ_max = 0.81 e Å⁻³
1962 reflections	Δρ_min = −1.31 e Å⁻³
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

	x	y	z	U_iso*/U_eq
I1	0.82998 (3)	0.69287 (4)	0.01561 (3)	0.0307 (1)
O1	0.7295 (3)	0.3497 (4)	0.0975 (2)	0.0276 (10)
C1	0.6122 (4)	0.4192 (6)	0.0508 (3)	0.0215 (14)
C1'	0.7158 (4)	0.1961 (7)	0.1533 (3)	0.0279 (16)
C2	0.6307 (4)	0.5768 (6)	0.0054 (3)	0.0214 (16)
C2'	0.8638 (5)	0.1475 (6)	0.1902 (4)	0.0286 (16)
C3	0.5180 (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)
H1'1	0.67420	0.10460	0.11080	0.0340*
H1'2	0.65390	0.21470	0.21010	0.0340*
H3	0.53150	0.76690	−0.07650	0.0210*
H2'1	0.92060	0.11840	0.13220	0.0340*
H2'2	0.85780	0.04420	0.23210	0.0340*
H3'1	0.94350	0.39070	0.20920	0.0290*
H3'2	0.88620	0.31150	0.30960	0.0290*
H4'1	1.14270	0.20610	0.22190	0.0310*
H4'2	1.08590	0.13140	0.32350	0.0310*
H5'1	1.12050	0.39790	0.40180	0.0400*
H5'2	1.16960	0.47950	0.29970	0.0400*
H6'1	1.32350	0.21600	0.40380	0.0560*
H6'2	1.36880	0.41260	0.40570	0.0560*
H6'3	1.37380	0.30610	0.30440	0.0560*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
I1	0.0231 (1)	0.0311 (2)	0.0374 (2)	−0.0054 (2)	−0.0051 (1)	0.0055 (2)
O1	0.0202 (14)	0.026 (2)	0.0358 (19)	−0.0003 (12)	−0.0093 (13)	0.0145 (15)
C1	0.019 (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)
C2	0.021 (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)
C3	0.0108 (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—C2	2.091 (4)	C2'—H2'1	0.9900
O1—C1	1.367 (5)	C2'—H2'2	0.9900
O1—C1'	1.428 (6)	C3—H3	0.9500
C1—C2	1.393 (6)	C3'—H3'1	0.9900
C1—C3ⁱ	1.375 (6)	C3'—H3'2	0.9900
C1'—C2'	1.515 (6)	C4'—H4'1	0.9900
C2—C3	1.405 (6)	C4'—H4'2	0.9900
C2'—C3'	1.515 (7)	C5'—H5'1	0.9900
C3'—C4'	1.514 (6)	C5'—H5'2	0.9900
C4'—C5'	1.524 (7)	C6'—H6'1	0.9800
C5'—C6'	1.526 (7)	C6'—H6'2	0.9800
C1'—H1'1	0.9900	C6'—H6'3	0.9800
C1'—H1'2	0.9900

I1···O1	3.073 (3)	H2'1···H4'1	2.4800
I1···C6'ⁱⁱ	3.736 (5)	H2'2···H4'2	2.5400
I1···H3'2ⁱⁱⁱ	3.3100	H2'2···O1^vii	2.9000
I1···H4'1^iv	3.3100	H2'2···C1^vii	3.0800
O1···I1	3.073 (3)	H3'1···O1	2.4900
O1···H3'1	2.4900	H3'1···H5'2	2.5200
O1···H2'2ⁱⁱⁱ	2.9000	H3'2···H5'1	2.5900
O1···H6'1^v	2.8300	H3'2···I1^vii	3.3100
C6'···I1^vi	3.736 (5)	H4'1···H2'1	2.4800
C1···H4'2ⁱⁱⁱ	3.0600	H4'1···H6'3	2.5400
C1···H4'2^v	3.0900	H4'1···H5'2^vi	2.5400
C1···H2'2ⁱⁱⁱ	3.0800	H4'1···I1^iv	3.3100
C1···H6'1^v	3.0500	H4'2···H2'2	2.5400
C1'···H3ⁱ	2.5400	H4'2···H6'1	2.5400
C2···H4'2^v	2.9600	H4'2···C1^vii	3.0600
C3···H5'1ⁱⁱⁱ	3.0300	H4'2···C1^viii	3.0900
C3···H1'2ⁱ	2.8700	H4'2···C2^viii	2.9600
C3···H4'2^v	2.9600	H4'2···C3^viii	2.9600
C3···H1'1ⁱ	2.7200	H5'1···H3'2	2.5900
H1'1···C3ⁱ	2.7200	H5'1···C3^vii	3.0300
H1'1···H3ⁱ	2.2200	H5'2···H3'1	2.5200
H1'2···C3ⁱ	2.8700	H5'2···H4'1ⁱⁱ	2.5400
H1'2···H3ⁱ	2.4700	H6'1···H4'2	2.5400
H3···C1'ⁱ	2.5400	H6'1···O1^viii	2.8300
H3···H1'1ⁱ	2.2200	H6'1···C1^viii	3.0500
H3···H1'2ⁱ	2.4700	H6'3···H4'1	2.5400

C1—O1—C1'	119.4 (3)	C2—C3—H3	121.00
O1—C1—C2	116.3 (3)	C1ⁱ—C3—H3	121.00
O1—C1—C3ⁱ	123.5 (4)	C2'—C3'—H3'1	109.00
C2—C1—C3ⁱ	120.2 (4)	C2'—C3'—H3'2	109.00
O1—C1'—C2'	106.5 (3)	C4'—C3'—H3'1	109.00
I1—C2—C1	119.0 (3)	C4'—C3'—H3'2	109.00
I1—C2—C3	119.7 (3)	H3'1—C3'—H3'2	108.00
C1—C2—C3	121.3 (4)	C3'—C4'—H4'1	109.00
C1'—C2'—C3'	114.1 (4)	C3'—C4'—H4'2	109.00
C1ⁱ—C3—C2	118.5 (4)	C5'—C4'—H4'1	109.00
C2'—C3'—C4'	112.5 (4)	C5'—C4'—H4'2	109.00
C3'—C4'—C5'	113.5 (4)	H4'1—C4'—H4'2	108.00
C4'—C5'—C6'	112.1 (4)	C4'—C5'—H5'1	109.00
O1—C1'—H1'1	110.00	C4'—C5'—H5'2	109.00
O1—C1'—H1'2	110.00	C6'—C5'—H5'1	109.00
C2'—C1'—H1'1	110.00	C6'—C5'—H5'2	109.00
C2'—C1'—H1'2	110.00	H5'1—C5'—H5'2	108.00
H1'1—C1'—H1'2	109.00	C5'—C6'—H6'1	109.00
C1'—C2'—H2'1	109.00	C5'—C6'—H6'2	109.00
C1'—C2'—H2'2	109.00	C5'—C6'—H6'3	110.00
C3'—C2'—H2'1	109.00	H6'1—C6'—H6'2	109.00
C3'—C2'—H2'2	109.00	H6'1—C6'—H6'3	110.00
H2'1—C2'—H2'2	108.00	H6'2—C6'—H6'3	110.00

C1'—O1—C1—C2	174.3 (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—C3	179.2 (4)	C1'—C2'—C3'—C4'	−177.7 (4)
C3ⁱ—C1—C2—I1	179.5 (3)	C2'—C3'—C4'—C5'	178.6 (4)
C3ⁱ—C1—C2—C3	0.2 (6)	C3'—C4'—C5'—C6'	−176.7 (4)
O1—C1—C3ⁱ—C2ⁱ	−179.1 (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) x−1/2, −y+1/2, z−1/2; (vi) −x+5/2, y−1/2, −z+1/2; (vii) −x+3/2, y−1/2, −z+1/2; (viii) x+1/2, −y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₈H₂₈I₂O₂
M_r	530.20
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	173
a, b, c (Å)	9.4481 (9), 7.8455 (6), 13.457 (2)
β (°)	92.148 (12)
V (Å³)	996.80 (16)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	3.16
Crystal size (mm)	0.32 × 0.11 × 0.06

Data collection
Diffractometer	STOE IPDS diffractometer
Absorption correction	Multi-scan MULscanABS in PLATON (Spek, 2009)
T_min, T_max	0.952, 1.042
No. of measured, independent and observed [I > 2σ(I)] reflections	7660, 1962, 1216
R_int	0.058
(sin θ/λ)_max (Å⁻¹)	0.618

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.029, 0.055, 0.79
No. of reflections	1962
No. of parameters	101
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	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···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+3/2, y-1/2, -z+1/2.

References

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

doi:10.1107/S1600536810005258

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