(E)-1-(2,4,6-Trimeth­oxy­phen­yl)pent-1-en-3-one

Collas, A.; Blockhuys, F.

doi:10.1107/S1600536810034641

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 66| Part 10| October 2010| Pages o2525-o2526

doi:10.1107/S1600536810034641

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(E)-1-(2,4,6-Trimethoxyphenyl)pent-1-en-3-one

Alain Collas ^a and Frank Blockhuys ^a ^*

^aDepartment of Chemistry, University of Antwerp, Universiteitsplein 1, B-2610 Wilrijk, Belgium
^*Correspondence e-mail: frank.blockhuys@ua.ac.be

(Received 30 July 2010; accepted 27 August 2010; online 11 September 2010)

The title compound, C₁₄H₁₈O₄, was obtained unintentionally as the major product of an attempted synthesis of (E,E)-2,5-bis[2-(2,4,6-trimethoxyphenyl)ethenyl]pyrazine. The crystal packing features layers based on two weak C—H⋯O hydrogen bonds involving the O atom of the carbonyl group and two O_methoxy⋯C_methoxy interactions [3.109 (2) Å]. The sheets are interconnected via methoxy–methoxy dimers and C—H⋯π interactions.

Related literature

For related compounds containing the Ph—CH=CH—CO— fragment, see: Zhang et al. (2008 ); Degen & Bolte (1999 ); Zonouzi et al. (2009 ); Wang et al. (2005 ). For π-bridged donor–acceptor–donor systems as candidates for organic light-emitting diodes and their non-linear optical properties, see Liu et al. (2001 ); Grimsdale et al. (1997 ); Chemla (1987 ). For a description of the Cambridge Structural Database, see: Allen (2002 ).

Experimental

Crystal data

C₁₄H₁₈O₄
M_r = 250.28
Triclinic, $[P \overline 1]$
a = 6.8626 (8) Å
b = 8.297 (1) Å
c = 12.068 (2) Å
α = 71.96 (1)°
β = 84.28 (1)°
γ = 84.90 (1)°
V = 648.88 (15) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.3 × 0.24 × 0.18 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
4732 measured reflections
2366 independent reflections
1589 reflections with > 2/s(I)
R_int = 0.020
3 standard reflections every 60 min intensity decay: none

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.106
S = 1.03
2366 reflections
166 parameters
H-atom parameters constrained
Δρ_max = 0.14 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O4ⁱ	0.93	2.59	3.517 (2)	177
C31—H31C⋯O4ⁱ	0.96	2.70	3.286 (2)	120
C21—H21C⋯O2ⁱⁱ	0.96	2.76	3.419 (2)	127
C11—H11A⋯O4ⁱⁱⁱ	0.96	2.75	3.557 (2)	142
C12—H12C⋯O4^iv	0.96	2.76	3.706 (2)	167
C10—H10B⋯Cg^v	0.97	2.77	3.59	142
Symmetry codes: (i) x-1, y+1, z; (ii) -x+1, -y+1, -z+1; (iii) x-1, y, z; (iv) -x+3, -y-1, -z+2; (v) x+1, y, z.

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1996 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ), Mercury (Macrae et al., 2008 ) and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810034641/zl2296sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810034641/zl2296Isup2.hkl

checkCIF report

Comment top

π-Bridged donor-acceptor-donor (A—D—A) systems are promising candidates for electronic applications such as organic light-emitting diodes (Liu et al., 2001; Grimsdale et al., 1997), as they are expected to have electronic properties similar to those of conventional OPV-type systems but with a red-shifted emission spectrum. Moreover, due to their high degree of conjugation, these A—D—A oligomers are also excellent candidates for organic non-linear optic (NLO) media with a high second-order hyperpolarizability, γ (Chemla, 1987). In an attempt to synthesize the A—D—A system E,E-2,5-bis[2-(2,4,6-trimethoxyphenyl)ethenyl]pyrazine from dimethylpyrazine and the relevant benzaldehyde under standard condensation conditions, (E)-1-(2,4,6-trimethoxyphenyl)pent-1-en-3-one (Fig. 1) was obtained as the major product. In this compound the C=C bond is not disordered, in contrast to what is the case in the 3-methoxy-4-acetoxyphenyl derivative YODGOO (Zhang et al., 2008) and the molecule adopts the anti conformation indicating that there are no energetically beneficial intermolecular contacts favouring the syn conformation as in the unsubstituted DIBNEH (Degen & Bolte, 1999). The title compound displays two weak intramolecular hydrogen bonds involving the methoxy groups in the ortho positions of the phenyl ring, one in a five- and one in a six-membered ring configuration. In contrast, in the 2-hydroxy-5-bromophenyl derivative NORGOR (Zonouzi et al., 2009) a less stable six-membered ring configuration is observed due to the competing strong intermolecular O—H···O hydrogen bond with an adjacent molecule. In the 2-hydroxyphenyl derivative FONKEZ (Wang et al., 2005), the more favourable five-membered ring configuration is also seen. The packing of the title compound is determined in first instance by contacts between the methoxy groups. Two molecules (symmetry-related via an inversion centre) are connected into a dimer involving O2 and C11 of the methoxy groups in the 2- and 4-positions [C11···O2ⁱ, 3.109 (2) Å, 178.33 (12)°, symm. code i = 1 - x, -y, 1 - z] (Fig. 2); note that the C···O—C angle is almost linear. Sheets are then generated through two weak hydrogen bonds involving H5 (Table 1, entry 1) and H31C (entry 2) contacting the oxygen atom of the carbonyl group (O4). These sheets are then interconnected by four additional weak hydrogen bonds (Fig. 3): H21C and O2 are involved in a second dimer formation (entry 3), H11A and H12C contact the oxygen atom of the carbonyl (O4, entries 4 and 5) and H10B of the methylene group next to the carbonyl group generates a CH···π interaction with a nearby phenyl ring (entry 6).

Related literature top

For related compounds containing the Ph—CH=CH—CO— fragment, see: Zhang et al. (2008); Degen & Bolte (1999); Zonouzi et al. (2009); Wang et al. (2005). For π-bridged donor–acceptor–donor systems as candidates for organic light-emitting diodes and their non-linear optical properties, see Liu et al. (2001); Grimsdale et al. (1997); Chemla (1987). For a description of the Cambridge Structural Database, see: Allen (2002).

Experimental top

A solution of sodium (1.0 g, 0.04 mol) in ethanol (50 ml) was added dropwise to a solution of 2,4,6-trimethoxybenzaldehyde (5.6 g, 0.04 mol) and 2,5-dimethylpyrazine (2.2 g, 0.02 mol) in ethanol (150 ml) at room temperature and the reaction mixture was heated under reflux for 4 h. The resulting fluorescent yellow solution was poured into 500 ml of ice water and the precipitate was filtered off and isomerized to the all-E form in p-xylene with a catalytic amount of iodine. Crystals suitable for X-ray diffraction were grown by slow evaporation of a THF solution. The yield was 2.3 g (46%). M.p. (uncorrected) 401 K. ¹H NMR (CDCl₃, 400 MHz, TMS): δ 7.63 (td, 8 and 0.4 Hz, H5), 8.18 (ddd, 8, 2 and 1 Hz, H6), 8.27 (ddd, 8, 2 and 1 Hz, H4), 8.62 (td, 2 and 0.4 Hz, H2), H4 and H6 appear to be magnetically equivalent. ¹³C NMR (CDCl₃, 100 MHz, TMS): δ 121.59 (C2), 124.54 (C5), 130.24 (C6), 132.32 (C4), 142.46 (C1), 148.53 (C3).

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS (Enraf–Nonius, 1994); data reduction: XCAD4 (Harms & Wocadlo, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999), Mercury (Macrae et al., 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. : Molecular structure of the title compound showing the numbering scheme. Displacement ellipsoids are drawn at the 50% probability level; hydrogen atoms are represented by spheres with an arbitrary radius.
	Fig. 2. : Sheets formed by weak hydrogen bonds and O_methoxy···C_methoxy interactions.
	Fig. 3. : Interactions responsible for the stabilization of the crystal packing in the direction perpendicular to the the generated sheets.

(E)-1-(2,4,6-Trimethoxyphenyl)pent-1-en-3-one top

Crystal data top

C₁₄H₁₈O₄	Z = 2
M_r = 250.28	F(000) = 268
Triclinic, P1	D_x = 1.281 Mg m⁻³
Hall symbol: -P 1	Melting point: 401 K
a = 6.8626 (8) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.297 (1) Å	Cell parameters from 25 reflections
c = 12.068 (2) Å	θ = 5.8–10.7°
α = 71.96 (1)°	µ = 0.09 mm⁻¹
β = 84.28 (1)°	T = 293 K
γ = 84.90 (1)°	Prism, yellow
V = 648.88 (15) Å³	0.3 × 0.24 × 0.18 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.020
Radiation source: fine-focus sealed tube	θ_max = 25.3°, θ_min = 1.8°
Graphite monochromator	h = −8→8
non–profiled ω/2θ scans	k = −9→9
4732 measured reflections	l = −14→14
2366 independent reflections	3 standard reflections every 60 min
1589 reflections with > 2/s(I)	intensity decay: none

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.106	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0495P)² + 0.1212P] where P = (F_o² + 2F_c²)/3
2366 reflections	(Δ/σ)_max < 0.001
166 parameters	Δρ_max = 0.14 e Å⁻³
0 restraints	Δρ_min = −0.17 e Å⁻³

Crystal data top

C₁₄H₁₈O₄	γ = 84.90 (1)°
M_r = 250.28	V = 648.88 (15) Å³
Triclinic, P1	Z = 2
a = 6.8626 (8) Å	Mo Kα radiation
b = 8.297 (1) Å	µ = 0.09 mm⁻¹
c = 12.068 (2) Å	T = 293 K
α = 71.96 (1)°	0.3 × 0.24 × 0.18 mm
β = 84.28 (1)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.020
4732 measured reflections	3 standard reflections every 60 min
2366 independent reflections	intensity decay: none
1589 reflections with > 2/s(I)

Refinement top

R[F² > 2σ(F²)] = 0.037	0 restraints
wR(F²) = 0.106	H-atom parameters constrained
S = 1.03	Δρ_max = 0.14 e Å⁻³
2366 reflections	Δρ_min = −0.17 e Å⁻³
166 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

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
C12	1.6553 (3)	−0.2420 (2)	0.97422 (19)	0.0572 (5)
H12A	1.6978	−0.1867	1.0259	0.086*
H12B	1.7585	−0.2453	0.9149	0.086*
H12C	1.6235	−0.3558	1.0179	0.086*
O2	0.41445 (17)	0.31488 (16)	0.60482 (12)	0.0544 (4)
O1	0.90913 (18)	−0.12493 (15)	0.63577 (11)	0.0498 (3)
O3	0.95452 (17)	0.26141 (15)	0.84353 (11)	0.0508 (4)
C2	0.8301 (2)	0.0153 (2)	0.66303 (15)	0.0389 (4)
C1	0.9334 (2)	0.0684 (2)	0.73980 (14)	0.0373 (4)
O4	1.4852 (2)	−0.34752 (17)	0.81476 (13)	0.0675 (4)
C3	0.6593 (2)	0.1019 (2)	0.61907 (15)	0.0434 (4)
H3	0.5942	0.0657	0.5679	0.052*
C7	1.1125 (2)	−0.0161 (2)	0.79054 (14)	0.0383 (4)
H7	1.1607	0.0323	0.8414	0.046*
C6	0.8527 (2)	0.2139 (2)	0.76858 (14)	0.0375 (4)
C8	1.2193 (2)	−0.1515 (2)	0.77646 (16)	0.0440 (4)
H8	1.1771	−0.2042	0.7262	0.053*
C5	0.6805 (2)	0.3019 (2)	0.72569 (15)	0.0405 (4)
H5	0.6307	0.3975	0.7462	0.049*
C9	1.3985 (2)	−0.2232 (2)	0.83457 (15)	0.0414 (4)
C21	0.3216 (3)	0.4540 (3)	0.63919 (19)	0.0590 (5)
H21A	0.2956	0.4200	0.7226	0.088*
H21B	0.2003	0.4891	0.6027	0.088*
H21C	0.4061	0.5469	0.6155	0.088*
C10	1.4756 (3)	−0.1447 (2)	0.91735 (15)	0.0427 (4)
H10A	1.3731	−0.1395	0.9778	0.051*
H10B	1.5081	−0.0292	0.8748	0.051*
C4	0.5856 (2)	0.2428 (2)	0.65167 (15)	0.0408 (4)
C31	0.8968 (3)	0.4174 (2)	0.86731 (18)	0.0548 (5)
H31A	0.8984	0.5088	0.7953	0.082*
H31B	0.9863	0.4371	0.9174	0.082*
H31C	0.7667	0.4115	0.9053	0.082*
C11	0.8077 (3)	−0.1881 (2)	0.56160 (17)	0.0535 (5)
H11A	0.6802	−0.2198	0.5982	0.080*
H11B	0.8809	−0.2856	0.5486	0.080*
H11C	0.7938	−0.1015	0.4882	0.080*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C12	0.0540 (12)	0.0567 (12)	0.0682 (13)	0.0125 (9)	−0.0247 (10)	−0.0277 (10)
O2	0.0432 (7)	0.0571 (8)	0.0729 (9)	0.0161 (6)	−0.0281 (6)	−0.0321 (7)
O1	0.0480 (7)	0.0507 (7)	0.0651 (8)	0.0121 (6)	−0.0228 (6)	−0.0368 (7)
O3	0.0475 (7)	0.0496 (7)	0.0707 (9)	0.0177 (6)	−0.0281 (6)	−0.0391 (7)
C2	0.0383 (9)	0.0378 (9)	0.0456 (10)	0.0026 (7)	−0.0072 (7)	−0.0201 (8)
C1	0.0339 (9)	0.0384 (9)	0.0434 (10)	0.0034 (7)	−0.0085 (7)	−0.0177 (8)
O4	0.0663 (9)	0.0600 (9)	0.0944 (11)	0.0310 (7)	−0.0347 (8)	−0.0504 (8)
C3	0.0412 (10)	0.0478 (10)	0.0495 (11)	0.0017 (8)	−0.0167 (8)	−0.0241 (9)
C7	0.0358 (9)	0.0394 (9)	0.0452 (10)	0.0036 (7)	−0.0106 (7)	−0.0199 (8)
C6	0.0355 (9)	0.0389 (9)	0.0431 (9)	0.0025 (7)	−0.0095 (7)	−0.0190 (8)
C8	0.0435 (10)	0.0436 (10)	0.0538 (11)	0.0070 (8)	−0.0168 (8)	−0.0261 (9)
C5	0.0385 (9)	0.0364 (9)	0.0498 (10)	0.0063 (7)	−0.0096 (8)	−0.0181 (8)
C9	0.0405 (9)	0.0371 (9)	0.0497 (11)	0.0073 (8)	−0.0087 (8)	−0.0190 (8)
C21	0.0445 (11)	0.0633 (13)	0.0740 (14)	0.0208 (9)	−0.0200 (10)	−0.0298 (11)
C10	0.0436 (10)	0.0390 (9)	0.0485 (10)	0.0055 (8)	−0.0107 (8)	−0.0175 (8)
C4	0.0330 (9)	0.0431 (10)	0.0463 (10)	0.0042 (7)	−0.0098 (8)	−0.0132 (8)
C31	0.0526 (11)	0.0507 (11)	0.0773 (14)	0.0156 (9)	−0.0255 (10)	−0.0415 (11)
C11	0.0562 (11)	0.0568 (12)	0.0629 (12)	0.0039 (9)	−0.0177 (9)	−0.0385 (10)

Geometric parameters (Å, º) top

C12—C10	1.514 (2)	C7—H7	0.9300
C12—H12A	0.9600	C6—C5	1.390 (2)
C12—H12B	0.9600	C8—C9	1.463 (2)
C12—H12C	0.9600	C8—H8	0.9300
O2—C4	1.3620 (19)	C5—C4	1.381 (2)
O2—C21	1.423 (2)	C5—H5	0.9300
O1—C2	1.3584 (19)	C9—C10	1.508 (2)
O1—C11	1.4287 (19)	C21—H21A	0.9600
O3—C6	1.3629 (19)	C21—H21B	0.9600
O3—C31	1.4253 (19)	C21—H21C	0.9600
C2—C3	1.382 (2)	C10—H10A	0.9700
C2—C1	1.412 (2)	C10—H10B	0.9700
C1—C6	1.409 (2)	C31—H31A	0.9600
C1—C7	1.452 (2)	C31—H31B	0.9600
O4—C9	1.2206 (19)	C31—H31C	0.9600
C3—C4	1.385 (2)	C11—H11A	0.9600
C3—H3	0.9300	C11—H11B	0.9600
C7—C8	1.332 (2)	C11—H11C	0.9600

C10—C12—H12A	109.5	O4—C9—C8	118.99 (15)
C10—C12—H12B	109.5	O4—C9—C10	120.39 (15)
H12A—C12—H12B	109.5	C8—C9—C10	120.62 (14)
C10—C12—H12C	109.5	O2—C21—H21A	109.5
H12A—C12—H12C	109.5	O2—C21—H21B	109.5
H12B—C12—H12C	109.5	H21A—C21—H21B	109.5
C4—O2—C21	118.09 (13)	O2—C21—H21C	109.5
C2—O1—C11	118.44 (13)	H21A—C21—H21C	109.5
C6—O3—C31	119.00 (12)	H21B—C21—H21C	109.5
O1—C2—C3	122.66 (14)	C9—C10—C12	113.02 (14)
O1—C2—C1	115.88 (14)	C9—C10—H10A	109.0
C3—C2—C1	121.46 (14)	C12—C10—H10A	109.0
C6—C1—C2	116.34 (14)	C9—C10—H10B	109.0
C6—C1—C7	118.79 (15)	C12—C10—H10B	109.0
C2—C1—C7	124.87 (14)	H10A—C10—H10B	107.8
C2—C3—C4	119.62 (15)	O2—C4—C5	124.12 (15)
C2—C3—H3	120.2	O2—C4—C3	114.18 (14)
C4—C3—H3	120.2	C5—C4—C3	121.69 (15)
C8—C7—C1	130.83 (16)	O3—C31—H31A	109.5
C8—C7—H7	114.6	O3—C31—H31B	109.5
C1—C7—H7	114.6	H31A—C31—H31B	109.5
O3—C6—C5	121.97 (14)	O3—C31—H31C	109.5
O3—C6—C1	115.08 (13)	H31A—C31—H31C	109.5
C5—C6—C1	122.94 (14)	H31B—C31—H31C	109.5
C7—C8—C9	124.60 (15)	O1—C11—H11A	109.5
C7—C8—H8	117.7	O1—C11—H11B	109.5
C9—C8—H8	117.7	H11A—C11—H11B	109.5
C4—C5—C6	117.93 (15)	O1—C11—H11C	109.5
C4—C5—H5	121.0	H11A—C11—H11C	109.5
C6—C5—H5	121.0	H11B—C11—H11C	109.5

C11—O1—C2—C3	−2.0 (2)	C7—C1—C6—C5	−179.07 (16)
C11—O1—C2—C1	177.92 (16)	C1—C7—C8—C9	−179.80 (17)
O1—C2—C1—C6	179.96 (15)	O3—C6—C5—C4	−178.96 (16)
C3—C2—C1—C6	−0.1 (2)	C1—C6—C5—C4	0.0 (3)
O1—C2—C1—C7	−0.5 (3)	C7—C8—C9—O4	−179.72 (18)
C3—C2—C1—C7	179.42 (17)	C7—C8—C9—C10	0.1 (3)
O1—C2—C3—C4	179.20 (16)	O4—C9—C10—C12	−3.5 (3)
C1—C2—C3—C4	−0.8 (3)	C8—C9—C10—C12	176.69 (17)
C6—C1—C7—C8	−178.60 (19)	C21—O2—C4—C5	−3.7 (3)
C2—C1—C7—C8	1.9 (3)	C21—O2—C4—C3	176.19 (16)
C31—O3—C6—C5	−7.9 (3)	C6—C5—C4—O2	178.94 (16)
C31—O3—C6—C1	173.02 (16)	C6—C5—C4—C3	−0.9 (3)
C2—C1—C6—O3	179.50 (15)	C2—C3—C4—O2	−178.58 (16)
C7—C1—C6—O3	0.0 (2)	C2—C3—C4—C5	1.3 (3)
C2—C1—C6—C5	0.5 (3)

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O4ⁱ	0.93	2.59	3.517 (2)	177
C31—H31C···O4ⁱ	0.96	2.70	3.286 (2)	120
C21—H21C···O2ⁱⁱ	0.96	2.76	3.419 (2)	127
C11—H11A···O4ⁱⁱⁱ	0.96	2.75	3.557 (2)	142
C12—H12C···O4^iv	0.96	2.76	3.706 (2)	167
C10—H10B···Cg^v	0.97	2.77	3.59	142

Symmetry codes: (i) x−1, y+1, z; (ii) −x+1, −y+1, −z+1; (iii) x−1, y, z; (iv) −x+3, −y−1, −z+2; (v) x+1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₈O₄
M_r	250.28
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	6.8626 (8), 8.297 (1), 12.068 (2)
α, β, γ (°)	71.96 (1), 84.28 (1), 84.90 (1)
V (Å³)	648.88 (15)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.3 × 0.24 × 0.18

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	–
No. of measured, independent and observed [ > 2/s(I)] reflections	4732, 2366, 1589
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.602

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.106, 1.03
No. of reflections	2366
No. of parameters	166
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.14, −0.17

Computer programs: CAD-4 EXPRESS (Enraf–Nonius, 1994), XCAD4 (Harms & Wocadlo, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999), Mercury (Macrae et al., 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O4ⁱ	0.93	2.59	3.517 (2)	177
C31—H31C···O4ⁱ	0.96	2.70	3.286 (2)	120
C21—H21C···O2ⁱⁱ	0.96	2.76	3.419 (2)	127
C11—H11A···O4ⁱⁱⁱ	0.96	2.75	3.557 (2)	142
C12—H12C···O4^iv	0.96	2.76	3.706 (2)	167
C10—H10B···Cg^v	0.97	2.77	3.59	142

Symmetry codes: (i) x−1, y+1, z; (ii) −x+1, −y+1, −z+1; (iii) x−1, y, z; (iv) −x+3, −y−1, −z+2; (v) x+1, y, z.

Acknowledgements

AC wishes to thank the Institute for the Promotion of Innovation by Science and Technology in Flanders (IWT) for a predoctoral grant. Financial support by the University of Antwerp under grant No. GOA-2404 is gratefully acknowledged.

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Volume 66| Part 10| October 2010| Pages o2525-o2526

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