1,3-Diallyl-1H-anthra[1,2-d]imidazole-2,6,11(3H)-trione

Afrakssou, Z.; Rodi, Y.K.; Zouihri, H.; Essassi, E.M.; Ng, S.W.

doi:10.1107/S1600536810024748

organic compounds

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ISSN: 2056-9890

Volume 66| Part 7| July 2010| Page o1851

doi:10.1107/S1600536810024748

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1,3-Diallyl-1H-anthra[1,2-d]imidazole-2,6,11(3H)-trione

Zahra Afrakssou,^a Youssef Kandri Rodi,^a Hafid Zouihri,^b El Mokhtar Essassi ^c and Seik Weng Ng ^d ^*

^aLaboratoire de Chimie Organique Appliquée, Faculté des Sciences et Techniques, Université Sidi Mohamed Ben Abdallah, Fès, Morocco, ^bCNRST Division UATRS, Angle Allal Fassi/FAR, BP 8027 Hay Riad, Rabat, Morocco, ^cLaboratoire de Chimie Organique Hétérocyclique, Pôle de Compétences Pharmacochimie, Université Mohammed V-Agdal, BP 1014 Avenue Ibn Batout, Rabat, Morocco, and ^dDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 22 June 2010; accepted 24 June 2010; online 26 June 2010)

In the title compound, C₂₁H₁₆N₂O₃, the fused-ring system (r.m.s. deviation = 0.067 Å) is slightly buckled at the carbonyl C atom of the anthracenyl ring system [deviation = 0.177 (1) Å] that is closer to an allyl substituent. The two allyl units lie on the same side of the fused-ring plane but are oriented in opposite directions, with N—C—C—C torsion angles of 126.9 (2) and 116.7 (2)°. In the crystal, the molecules are linked into chains propagating along the b axis by C—H⋯O hydrogen bonds.

Related literature

For a related structure, see: Guimarães et al. (2009 ).

Experimental

Crystal data

C₂₁H₁₆N₂O₃
M_r = 344.36
Monoclinic, P 2₁ /c
a = 7.8539 (2) Å
b = 11.5822 (3) Å
c = 18.1455 (4) Å
β = 93.537 (1)°
V = 1647.47 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.40 × 0.35 × 0.20 mm

Data collection

Bruker X8 APEXII area-detector diffractometer
22612 measured reflections
4806 independent reflections 4805 in Refinement?
3053 reflections with I > 2σ(I)
R_int = 0.039

Refinement

R[F² > 2σ(F²)] = 0.049
wR(F²) = 0.153
S = 1.02
4805 reflections
236 parameters
H-atom parameters constrained
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13⋯O3ⁱ	0.93	2.49	3.406 (2)	168
C16—H16B⋯O3ⁱ	0.97	2.42	3.362 (2)	165
Symmetry code: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2008 ); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810024748/ci5112sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810024748/ci5112Isup2.hkl

checkCIF report

Comment top

An imidazol-one such as 1H-anthra[2,1-d]imidazole-2,6,11(3H)-trione, in which the five-membered ring is fused with an anthraquinone system, alkyl halides under catalytic conditions to yield di-N,N'-substituted derivatives that serve as starting reagents for the synthesis of other drugs. The anthraquinone system itself is found in a large number of pigments and dyes. The title compound (Scheme I, Fig. 1) is a deep orange material that may be useful as an organic fluorophone.

The title molecule features four rings that are fused together (r.m.s. deviation 0.067 Å). The fused-ring system is slightly buckled at that carbonyl C-atom, C3, of the anthracenyl system [0.177 (1) Å] that is closer to an allyl substituent. The pendant allyl units lie on the same side of the fused-ring plane but are oriented in opposite directions. The crystal packing is stabilized by C—H···O hydrogen bonds (Table 1).

Related literature top

For a related structure, see: Guimarães et al. (2009).

Experimental top

To a solution of 1H-anthra[2,1-d]imidazole-2,6,11(3H)-trione (1.00 g, 0.38 mmol), potassium carbonate (1.56 g,11 mmol) and tetra n-butyl ammonium bromide (0.12 g, 0.38 mmol) in DMF (20 ml)) was added allyl bromide (0.77 ml, 11 mmol). Stirring was continued at room temperature for 24 h. The mixture was filtered and the solvent removed. The residue was extracted with water. The organic compound was chromatographed on a column of silica gel with ethyl acetate-hexane (1/1) as eluent. Orange crystals were isolated when the solvent was allowed to evaporate.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

Fig. 1. Displacement ellipsoid plot (Barbour, 2001) of C₂₁H₁₆N₂O₃ at the 50% probability leve. H atoms are drawn as spheres of arbitrary radii.

1,3-Diallyl-1H-anthra[1,2-d]imidazole-2,6,11(3H)-trione top

Crystal data top

C₂₁H₁₆N₂O₃	F(000) = 720
M_r = 344.36	D_x = 1.388 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4815 reflections
a = 7.8539 (2) Å	θ = 2.2–29.4°
b = 11.5822 (3) Å	µ = 0.09 mm⁻¹
c = 18.1455 (4) Å	T = 293 K
β = 93.537 (1)°	Block, orange
V = 1647.47 (7) Å³	0.40 × 0.35 × 0.20 mm
Z = 4

Data collection top

Bruker X8 APEXII area-detector diffractometer	3053 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.039
Graphite monochromator	θ_max = 30.0°, θ_min = 2.1°
ϕ and ω scans	h = −11→11
22612 measured reflections	k = −16→16
4806 independent reflections	l = −25→25

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)] = 0.049	H-atom parameters constrained
wR(F²) = 0.153	w = 1/[σ²(F_o²) + (0.0755P)² + 0.2066P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max = 0.001
4805 reflections	Δρ_max = 0.31 e Å⁻³
236 parameters	Δρ_min = −0.22 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0033 (11)

Crystal data top

C₂₁H₁₆N₂O₃	V = 1647.47 (7) Å³
M_r = 344.36	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.8539 (2) Å	µ = 0.09 mm⁻¹
b = 11.5822 (3) Å	T = 293 K
c = 18.1455 (4) Å	0.40 × 0.35 × 0.20 mm
β = 93.537 (1)°

Data collection top

Bruker X8 APEXII area-detector diffractometer	3053 reflections with I > 2σ(I)
22612 measured reflections	R_int = 0.039
4806 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	0 restraints
wR(F²) = 0.153	H-atom parameters constrained
S = 1.02	Δρ_max = 0.31 e Å⁻³
4805 reflections	Δρ_min = −0.22 e Å⁻³
236 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.14067 (16)	0.31774 (10)	0.53905 (6)	0.0588 (3)
O2	0.23915 (17)	0.77316 (10)	0.53322 (7)	0.0623 (3)
O3	0.44816 (18)	0.19062 (10)	0.30395 (6)	0.0633 (4)
N1	0.35081 (16)	0.29295 (10)	0.40381 (6)	0.0405 (3)
N2	0.42897 (16)	0.38962 (10)	0.30579 (6)	0.0422 (3)
C1	0.32994 (17)	0.40923 (11)	0.41903 (7)	0.0342 (3)
C2	0.27111 (16)	0.47213 (11)	0.47863 (7)	0.0342 (3)
C3	0.18650 (18)	0.41799 (12)	0.54058 (7)	0.0387 (3)
C4	0.14672 (17)	0.49192 (13)	0.60472 (8)	0.0408 (3)
C5	0.0848 (2)	0.43992 (15)	0.66656 (9)	0.0532 (4)
H5	0.0729	0.3601	0.6683	0.064*
C6	0.0408 (2)	0.50686 (19)	0.72553 (9)	0.0635 (5)
H6	−0.0001	0.4719	0.7671	0.076*
C7	0.0572 (2)	0.62479 (19)	0.72301 (10)	0.0649 (5)
H7	0.0265	0.6693	0.7627	0.078*
C8	0.1187 (2)	0.67763 (16)	0.66225 (10)	0.0557 (4)
H8	0.1301	0.7575	0.6610	0.067*
C9	0.16416 (18)	0.61104 (13)	0.60235 (8)	0.0427 (3)
C10	0.22782 (18)	0.66824 (13)	0.53631 (8)	0.0428 (3)
C11	0.27960 (17)	0.59389 (12)	0.47464 (7)	0.0372 (3)
C12	0.3362 (2)	0.64983 (13)	0.41289 (8)	0.0443 (3)
H12	0.3403	0.7301	0.4122	0.053*
C13	0.38660 (19)	0.58851 (12)	0.35255 (8)	0.0437 (3)
H13	0.4219	0.6261	0.3108	0.052*
C14	0.38263 (17)	0.47023 (12)	0.35652 (7)	0.0368 (3)
C15	0.4124 (2)	0.28065 (13)	0.33395 (8)	0.0451 (4)
C16	0.4861 (2)	0.40982 (14)	0.23155 (7)	0.0462 (4)
H16A	0.5829	0.3603	0.2237	0.055*
H16B	0.5234	0.4893	0.2277	0.055*
C17	0.3483 (2)	0.38657 (17)	0.17310 (9)	0.0595 (5)
H17	0.3070	0.3114	0.1688	0.071*
C18	0.2826 (3)	0.4620 (2)	0.12858 (11)	0.0851 (7)
H18A	0.3206	0.5380	0.1312	0.102*
H18B	0.1969	0.4409	0.0935	0.102*
C19	0.3537 (2)	0.18926 (12)	0.45100 (8)	0.0431 (3)
H19A	0.3615	0.2133	0.5023	0.052*
H19B	0.4552	0.1448	0.4424	0.052*
C20	0.2018 (2)	0.11366 (14)	0.43818 (8)	0.0498 (4)
H20	0.0939	0.1461	0.4403	0.060*
C21	0.2140 (3)	0.00335 (17)	0.42404 (11)	0.0695 (5)
H21A	0.3207	−0.0307	0.4217	0.083*
H21B	0.1158	−0.0411	0.4163	0.083*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0796 (8)	0.0408 (6)	0.0591 (7)	−0.0081 (6)	0.0298 (6)	−0.0009 (5)
O2	0.0821 (9)	0.0354 (6)	0.0711 (8)	−0.0067 (6)	0.0191 (6)	−0.0114 (5)
O3	0.1046 (10)	0.0388 (6)	0.0494 (7)	0.0101 (6)	0.0285 (6)	−0.0027 (5)
N1	0.0577 (7)	0.0304 (6)	0.0343 (6)	0.0046 (5)	0.0110 (5)	0.0026 (4)
N2	0.0573 (7)	0.0374 (6)	0.0330 (6)	0.0023 (5)	0.0113 (5)	0.0013 (5)
C1	0.0386 (7)	0.0309 (6)	0.0332 (6)	0.0013 (5)	0.0033 (5)	0.0014 (5)
C2	0.0356 (7)	0.0342 (7)	0.0327 (6)	0.0008 (5)	0.0021 (5)	0.0006 (5)
C3	0.0418 (7)	0.0374 (7)	0.0373 (7)	0.0022 (6)	0.0067 (6)	0.0014 (6)
C4	0.0381 (7)	0.0484 (8)	0.0363 (7)	0.0042 (6)	0.0048 (6)	−0.0015 (6)
C5	0.0589 (10)	0.0575 (10)	0.0447 (8)	0.0056 (8)	0.0151 (7)	0.0033 (7)
C6	0.0697 (11)	0.0793 (13)	0.0434 (9)	0.0053 (10)	0.0189 (8)	−0.0030 (9)
C7	0.0712 (12)	0.0783 (14)	0.0465 (9)	0.0071 (10)	0.0143 (8)	−0.0192 (9)
C8	0.0608 (10)	0.0552 (10)	0.0518 (9)	0.0046 (8)	0.0077 (8)	−0.0152 (8)
C9	0.0399 (7)	0.0472 (8)	0.0409 (7)	0.0030 (6)	0.0024 (6)	−0.0077 (6)
C10	0.0443 (8)	0.0376 (8)	0.0466 (8)	−0.0008 (6)	0.0034 (6)	−0.0079 (6)
C11	0.0395 (7)	0.0330 (7)	0.0392 (7)	0.0004 (5)	0.0028 (6)	−0.0015 (5)
C12	0.0560 (9)	0.0311 (7)	0.0462 (8)	−0.0028 (6)	0.0064 (7)	0.0023 (6)
C13	0.0548 (9)	0.0366 (7)	0.0404 (7)	−0.0025 (6)	0.0087 (6)	0.0061 (6)
C14	0.0408 (7)	0.0361 (7)	0.0339 (7)	0.0010 (6)	0.0052 (5)	0.0013 (5)
C15	0.0618 (9)	0.0382 (8)	0.0365 (7)	0.0053 (7)	0.0123 (7)	0.0003 (6)
C16	0.0564 (9)	0.0479 (8)	0.0360 (7)	−0.0006 (7)	0.0158 (6)	0.0019 (6)
C17	0.0686 (11)	0.0708 (12)	0.0406 (8)	−0.0083 (9)	0.0168 (8)	−0.0026 (8)
C18	0.0780 (14)	0.131 (2)	0.0468 (10)	0.0076 (13)	0.0107 (9)	0.0108 (12)
C19	0.0573 (9)	0.0331 (7)	0.0394 (7)	0.0057 (6)	0.0076 (6)	0.0057 (6)
C20	0.0611 (10)	0.0430 (8)	0.0458 (8)	0.0004 (7)	0.0067 (7)	0.0062 (7)
C21	0.0869 (13)	0.0486 (10)	0.0739 (13)	−0.0104 (10)	0.0114 (10)	−0.0024 (9)

Geometric parameters (Å, º) top

O1—C3	1.2154 (18)	C8—H8	0.93
O2—C10	1.2200 (18)	C9—C10	1.483 (2)
O3—C15	1.2170 (17)	C10—C11	1.4884 (19)
N1—C1	1.3867 (16)	C11—C12	1.3908 (19)
N1—C15	1.3918 (18)	C12—C13	1.383 (2)
N1—C19	1.4742 (17)	C12—H12	0.93
N2—C15	1.3708 (19)	C13—C14	1.372 (2)
N2—C14	1.3757 (17)	C13—H13	0.93
N2—C16	1.4647 (17)	C16—C17	1.493 (2)
C1—C2	1.4056 (18)	C16—H16A	0.97
C1—C14	1.4194 (18)	C16—H16B	0.97
C2—C11	1.4139 (19)	C17—C18	1.277 (3)
C2—C3	1.4800 (18)	C17—H17	0.93
C3—C4	1.4934 (19)	C18—H18A	0.93
C4—C9	1.387 (2)	C18—H18B	0.93
C4—C5	1.388 (2)	C19—C20	1.486 (2)
C5—C6	1.382 (2)	C19—H19A	0.97
C5—H5	0.93	C19—H19B	0.97
C6—C7	1.373 (3)	C20—C21	1.308 (2)
C6—H6	0.93	C20—H20	0.93
C7—C8	1.375 (3)	C21—H21A	0.93
C7—H7	0.93	C21—H21B	0.93
C8—C9	1.397 (2)

C1—N1—C15	109.44 (11)	C2—C11—C10	121.50 (12)
C1—N1—C19	132.32 (11)	C13—C12—C11	121.32 (13)
C15—N1—C19	116.86 (11)	C13—C12—H12	119.3
C15—N2—C14	109.90 (11)	C11—C12—H12	119.3
C15—N2—C16	122.09 (12)	C14—C13—C12	117.55 (13)
C14—N2—C16	128.00 (12)	C14—C13—H13	121.2
N1—C1—C2	134.84 (12)	C12—C13—H13	121.2
N1—C1—C14	106.28 (11)	C13—C14—N2	129.39 (13)
C2—C1—C14	118.87 (12)	C13—C14—C1	123.19 (13)
C1—C2—C11	117.30 (12)	N2—C14—C1	107.40 (12)
C1—C2—C3	123.31 (12)	O3—C15—N2	126.33 (14)
C11—C2—C3	119.10 (12)	O3—C15—N1	126.71 (14)
O1—C3—C2	122.25 (13)	N2—C15—N1	106.95 (12)
O1—C3—C4	119.32 (13)	N2—C16—C17	112.01 (13)
C2—C3—C4	118.31 (12)	N2—C16—H16A	109.2
C9—C4—C5	119.78 (14)	C17—C16—H16A	109.2
C9—C4—C3	121.35 (13)	N2—C16—H16B	109.2
C5—C4—C3	118.81 (14)	C17—C16—H16B	109.2
C6—C5—C4	119.96 (17)	H16A—C16—H16B	107.9
C6—C5—H5	120.0	C18—C17—C16	125.0 (2)
C4—C5—H5	120.0	C18—C17—H17	117.5
C7—C6—C5	120.24 (17)	C16—C17—H17	117.5
C7—C6—H6	119.9	C17—C18—H18A	120.0
C5—C6—H6	119.9	C17—C18—H18B	120.0
C6—C7—C8	120.54 (16)	H18A—C18—H18B	120.0
C6—C7—H7	119.7	N1—C19—C20	113.92 (13)
C8—C7—H7	119.7	N1—C19—H19A	108.8
C7—C8—C9	119.83 (18)	C20—C19—H19A	108.8
C7—C8—H8	120.1	N1—C19—H19B	108.8
C9—C8—H8	120.1	C20—C19—H19B	108.8
C4—C9—C8	119.64 (15)	H19A—C19—H19B	107.7
C4—C9—C10	120.54 (13)	C21—C20—C19	122.60 (17)
C8—C9—C10	119.81 (15)	C21—C20—H20	118.7
O2—C10—C9	120.76 (13)	C19—C20—H20	118.7
O2—C10—C11	121.17 (14)	C20—C21—H21A	120.0
C9—C10—C11	118.07 (13)	C20—C21—H21B	120.0
C12—C11—C2	121.62 (13)	H21A—C21—H21B	120.0
C12—C11—C10	116.87 (13)

C15—N1—C1—C2	178.83 (15)	C1—C2—C11—C10	−177.23 (12)
C19—N1—C1—C2	−15.3 (3)	C3—C2—C11—C10	8.7 (2)
C15—N1—C1—C14	−0.69 (16)	O2—C10—C11—C12	−1.9 (2)
C19—N1—C1—C14	165.13 (14)	C9—C10—C11—C12	179.00 (13)
N1—C1—C2—C11	176.13 (15)	O2—C10—C11—C2	178.30 (14)
C14—C1—C2—C11	−4.39 (18)	C9—C10—C11—C2	−0.8 (2)
N1—C1—C2—C3	−10.1 (2)	C2—C11—C12—C13	0.1 (2)
C14—C1—C2—C3	169.38 (12)	C10—C11—C12—C13	−179.75 (14)
C1—C2—C3—O1	−10.6 (2)	C11—C12—C13—C14	−1.6 (2)
C11—C2—C3—O1	163.09 (14)	C12—C13—C14—N2	−178.38 (14)
C1—C2—C3—C4	173.42 (12)	C12—C13—C14—C1	−0.1 (2)
C11—C2—C3—C4	−12.91 (19)	C15—N2—C14—C13	176.95 (15)
O1—C3—C4—C9	−166.55 (14)	C16—N2—C14—C13	−3.9 (3)
C2—C3—C4—C9	9.6 (2)	C15—N2—C14—C1	−1.58 (16)
O1—C3—C4—C5	10.9 (2)	C16—N2—C14—C1	177.55 (14)
C2—C3—C4—C5	−172.99 (13)	N1—C1—C14—C13	−177.27 (13)
C9—C4—C5—C6	0.0 (2)	C2—C1—C14—C13	3.1 (2)
C3—C4—C5—C6	−177.51 (15)	N1—C1—C14—N2	1.38 (15)
C4—C5—C6—C7	0.4 (3)	C2—C1—C14—N2	−178.24 (12)
C5—C6—C7—C8	−0.5 (3)	C14—N2—C15—O3	−177.54 (17)
C6—C7—C8—C9	0.3 (3)	C16—N2—C15—O3	3.3 (3)
C5—C4—C9—C8	−0.2 (2)	C14—N2—C15—N1	1.15 (17)
C3—C4—C9—C8	177.27 (14)	C16—N2—C15—N1	−178.04 (13)
C5—C4—C9—C10	−179.13 (14)	C1—N1—C15—O3	178.43 (16)
C3—C4—C9—C10	−1.7 (2)	C19—N1—C15—O3	10.1 (3)
C7—C8—C9—C4	0.0 (2)	C1—N1—C15—N2	−0.26 (18)
C7—C8—C9—C10	178.99 (15)	C19—N1—C15—N2	−168.54 (12)
C4—C9—C10—O2	178.08 (14)	C15—N2—C16—C17	76.63 (19)
C8—C9—C10—O2	−0.9 (2)	C14—N2—C16—C17	−102.40 (18)
C4—C9—C10—C11	−2.8 (2)	N2—C16—C17—C18	116.73 (19)
C8—C9—C10—C11	178.24 (14)	C1—N1—C19—C20	109.60 (18)
C1—C2—C11—C12	2.9 (2)	C15—N1—C19—C20	−85.41 (17)
C3—C2—C11—C12	−171.10 (13)	N1—C19—C20—C21	126.87 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···O3ⁱ	0.93	2.49	3.406 (2)	168
C16—H16B···O3ⁱ	0.97	2.42	3.362 (2)	165

Symmetry code: (i) −x+1, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₂₁H₁₆N₂O₃
M_r	344.36
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	7.8539 (2), 11.5822 (3), 18.1455 (4)
β (°)	93.537 (1)
V (Å³)	1647.47 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.40 × 0.35 × 0.20

Data collection
Diffractometer	Bruker X8 APEXII area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	22612, 4806, 3053
R_int	0.039
(sin θ/λ)_max (Å⁻¹)	0.703

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.153, 1.02
No. of reflections	4805
No. of parameters	236
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.22

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···O3ⁱ	0.93	2.49	3.406 (2)	168
C16—H16B···O3ⁱ	0.97	2.42	3.362 (2)	165

Symmetry code: (i) −x+1, y+1/2, −z+1/2.

Acknowledgements

The authors thank Université Mohammed V-Agdal and the University of Malaya for supporting this study.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Guimarães, T. T., Da Silva Júnior, E. N., Carvalho, C. E. M., De Simone, C. A. & Pinto, A. V. (2009). Acta Cryst. E65, o1063. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43. Submitted. Google Scholar