2-(1,3-Dioxoisoindolin-2-yl)acetonitrile

Aouine, Y.; Alami, A.; El Hallaoui, A.; Elachqar, A.; Zouihri, H.

doi:10.1107/S1600536810037335

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 10| October 2010| Page o2631

doi:10.1107/S1600536810037335

Open

access

2-(1,3-Dioxoisoindolin-2-yl)acetonitrile

Younas Aouine,^a Anouar Alami,^a ^* Abdelilah El Hallaoui,^a Abdelrhani Elachqar ^a and Hafid Zouihri ^b

^aLaboratoire de Chimie Organique, Faculté des Sciences, Dhar el Mahraz, Université Sidi Mohammed Ben Abdellah, Fès, Morocco, and ^bLaboratoires de Diffraction des Rayons X, Division UATRS, Centre National pour la Recherche Scientifique et Technique, Rabat, Morocco
^*Correspondence e-mail: alamianouar@yahoo.fr

(Received 8 September 2010; accepted 17 September 2010; online 25 September 2010)

The asymmetric unit of the title compound, C₁₀H₆N₂O₂, contains two independent molecules. The dihedral angles between the acetonitrile and the 1H-isoindole-1,3(2H)-dione units are 69.0 (7)° and 77.0 (5)° in the two molecules. One of the two terminal N atoms is disordered over two positions in a 0.66 (8):0,34 (8) ratio. In the crystal structure, the molecules are linked by intermolecular C—H⋯O hydrogen bonds.

Related literature

The title compound was prepared as a key intermediate for the synthesis of a new new tetrazolic derivative. For the use of tetrazoles as pesticides, see: Schocken et al. (1989 ); Yanagi et al. (2001 ); Lim et al. (2007 ) and as antihypertensive, antialergic, antibiotic and anticonvulsant agents, see: Hashimoto et al. (1998 ); Berghmans et al. (2007 ). For their use in cancer, AIDS and obesity treatments, see: Tamura et al. (1998 ); Shih et al. (1999 ); Muraglia et al. (2006 ). A major advantage of tetrazoles over carboxylic acids is that they are resistant to many biological metabolic degradation pathways, see: Singh et al. (1980 ).

Experimental

Crystal data

C₁₀H₆N₂O₂
M_r = 186.17
Triclinic, $[P \overline 1]$
a = 8.0960 (2) Å
b = 8.4371 (2) Å
c = 14.3118 (3) Å
α = 85.072 (1)°
β = 79.272 (1)°
γ = 68.421 (1)°
V = 893.02 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 296 K
0.25 × 0.24 × 0.16 mm

Data collection

Bruker APEXII CCD detector diffractometer
18332 measured reflections
3906 independent reflections
2885 reflections with I > 2σ(I)
R_int = 0.034

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.128
S = 1.05
3906 reflections
267 parameters
6 restraints
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13⋯O12ⁱ	0.93	2.51	3.386 (2)	158
C15—H15⋯O20ⁱⁱ	0.93	2.45	3.144 (2)	132
C18—H18B⋯O20	0.97	2.42	3.372 (2)	167
C28—H28A⋯O21ⁱⁱⁱ	0.97	2.39	3.298 (2)	156
Symmetry codes: (i) x, y-1, z; (ii) -x+2, -y+1, -z; (iii) -x+2, -y, -z+1.

Data collection: APEX2 (Bruker, 2005 ); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810037335/jh2206sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810037335/jh2206Isup2.hkl

checkCIF report

Comment top

With the aim of developing new tetrazolic derived, an analog isosteric of the glycine, we have prepared 2-(1,3-dioxoisoindolin-2-yl)acetonitrile,a key intermediate, starting from 2-(bromomethyl)isoindoline-1,3-dione.

The asymmetric unit of the new synthetized 2-(1,3-dioxoisoindolin-2-yl)acetonitrile, C₁₀H₆N₂O₂, contains two independent molecules. The dihedral angles between the acetonitrile and the 1H-isoindole-1,3(2H)-dione are 69.0 (7)° and 77.0 (5)°, respictively.

One of the two terminal N is disordered over two positions with occupancy of 0.66 (8) for the major site. In the crystal structure, the molecules are linked by intermolecular C—H···O hydrogen bonds.

Related literature top

For the use of tetrazoles as pesticides, see: Schocken et al. (1989); Yanagi et al. (2001); Lim et al. (2007) and as antihypertensive, antialergic, antibiotic and anticonvulsant agents, see: Hashimoto et al. (1998); Berghmans et al. (2007). For their use in cancer, AIDS and obesity treatments, see: Tamura et al. (1998); Shih et al. (1999); Muraglia et al. (2006). A major advantage of tetrazoles over carboxylic acids is that they are resistant to many biological metabolic degradation pathways, see: Singh et al. (1980).

Experimental top

A mixture containing 4.8 g (0.02 mol) of 2-(bromomethyl)isoindoline-1,3-dione, 6.5 g KCN (0.1 mol), and 60 ml of anhydrous acetonitrile is heated overnight at 60°C, and then filtered. The residue is washed twice with acetonitrile, and the filtrate was concentrated under vacuum. The solid obtained is purified by chromatography on silica gel column (eluent: ether / hexane: 2 / 3).

Yield= 80% (white solid); F= 122–124°C; Rf = 0.31(ether/hexane3:1).

IR (KBr) ν cm^-1: 3070(CH_arom),2947/2983 (CH), 1692/1709 (2 C=O), 1557/1613 (C=C). δ_H (CDCl₃): 4.57 (2H_CH2,s); 7.60–8.10 (4H_arom, m). δ_C (CDCl₃): 28.1(CH₂);115.01(CN); 127.5; 132.1; 133.3(C_arom); 168.28(2 C=O).

MS—EI: [M]⁺=186.

Elemental analysis for C₁₀H₆N₂O₂ Calcd(Found):C 64.51(64.62), H 3.22(3.31), N 15.02(14.94).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. Two independent molecules of the title compound showing the atom-labelling scheme and 30% probability displacement ellipsoids. Only major parts of disordered N are shown.
	Fig. 2. Partial packing view showing the formation of a chain through C—H···O hydrogen bonds shown as dashed lines.
	Fig. 3. View of the title compound showing displacement ellipsoids at the 50% probability level.

2-(1,3-Dioxoisoindolin-2-yl)acetonitrile top

Crystal data top

C₁₀H₆N₂O₂	Z = 4
M_r = 186.17	F(000) = 384
Triclinic, P1	D_x = 1.385 Mg m⁻³
Hall symbol: -P 1	Melting point: 395 K
a = 8.0960 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.4371 (2) Å	Cell parameters from 2714 reflections
c = 14.3118 (3) Å	θ = 2.7–25.3°
α = 85.072 (1)°	µ = 0.10 mm⁻¹
β = 79.272 (1)°	T = 296 K
γ = 68.421 (1)°	Block, colourless
V = 893.02 (4) Å³	0.25 × 0.24 × 0.16 mm

Data collection top

Bruker APEXII CCD detector diffractometer	2885 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.034
Graphite monochromator	θ_max = 27.0°, θ_min = 1.5°
ω and ϕ scans	h = −10→10
18332 measured reflections	k = −10→10
3906 independent reflections	l = −17→18

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.128	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0697P)² + 0.070P] where P = (F_o² + 2F_c²)/3
3906 reflections	(Δ/σ)_max = 0.005
267 parameters	Δρ_max = 0.19 e Å⁻³
6 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₁₀H₆N₂O₂	γ = 68.421 (1)°
M_r = 186.17	V = 893.02 (4) Å³
Triclinic, P1	Z = 4
a = 8.0960 (2) Å	Mo Kα radiation
b = 8.4371 (2) Å	µ = 0.10 mm⁻¹
c = 14.3118 (3) Å	T = 296 K
α = 85.072 (1)°	0.25 × 0.24 × 0.16 mm
β = 79.272 (1)°

Data collection top

Bruker APEXII CCD detector diffractometer	2885 reflections with I > 2σ(I)
18332 measured reflections	R_int = 0.034
3906 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	6 restraints
wR(F²) = 0.128	H-atom parameters constrained
S = 1.05	Δρ_max = 0.19 e Å⁻³
3906 reflections	Δρ_min = −0.20 e Å⁻³
267 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	Occ. (<1)
C11	0.73565 (18)	0.39842 (17)	0.04371 (10)	0.0471 (3)
C16	0.75085 (18)	0.49910 (17)	−0.03635 (10)	0.0461 (3)
C10	0.7395 (2)	0.48752 (18)	0.12747 (11)	0.0497 (3)
C17	0.7711 (2)	0.65409 (18)	−0.00671 (11)	0.0527 (4)
C18	0.7772 (2)	0.76260 (19)	0.15037 (12)	0.0582 (4)
H18A	0.8360	0.8327	0.1112	0.070*
H18B	0.8503	0.7049	0.1984	0.070*
C15	0.7474 (2)	0.4505 (2)	−0.12523 (12)	0.0612 (4)
H15	0.7559	0.5195	−0.1788	0.073*
C14	0.7309 (2)	0.2948 (2)	−0.13128 (13)	0.0685 (5)
H14	0.7291	0.2577	−0.1903	0.082*
C19	0.5995 (3)	0.8711 (2)	0.19668 (15)	0.0745 (5)
C12	0.7182 (3)	0.2438 (2)	0.03696 (14)	0.0670 (5)
H12	0.7075	0.1754	0.0906	0.080*
C13	0.7170 (3)	0.1937 (2)	−0.05234 (15)	0.0750 (5)
H13	0.7065	0.0893	−0.0589	0.090*
C20	0.91639 (18)	0.46404 (18)	0.38170 (10)	0.0462 (3)
C26	0.72827 (18)	0.4498 (2)	0.52338 (10)	0.0495 (3)
C21	0.78905 (18)	0.56105 (19)	0.46334 (10)	0.0472 (3)
C27	0.81143 (19)	0.2782 (2)	0.48113 (11)	0.0512 (4)
C28	1.0390 (2)	0.1584 (2)	0.33559 (12)	0.0598 (4)
H28A	1.1202	0.0741	0.3727	0.072*
H28B	1.1114	0.2015	0.2857	0.072*
C22	0.7336 (2)	0.7317 (2)	0.48390 (12)	0.0600 (4)
H22	0.7740	0.8068	0.4433	0.072*
C29	0.9423 (2)	0.0764 (2)	0.29222 (14)	0.0661 (5)
C23	0.6146 (2)	0.7856 (2)	0.56814 (14)	0.0715 (5)
H23	0.5744	0.8996	0.5843	0.086*
C25	0.6098 (2)	0.5045 (3)	0.60702 (12)	0.0640 (4)
H25	0.5686	0.4297	0.6475	0.077*
C24	0.5549 (2)	0.6749 (3)	0.62815 (13)	0.0725 (5)
H24	0.4758	0.7154	0.6842	0.087*
O11	0.72249 (19)	0.44907 (16)	0.21083 (8)	0.0739 (4)
O12	0.7926 (2)	0.77161 (16)	−0.05386 (10)	0.0863 (4)
O20	1.00395 (15)	0.51155 (14)	0.31593 (8)	0.0613 (3)
O21	0.79522 (16)	0.14499 (15)	0.50949 (9)	0.0727 (4)
N11	0.76467 (16)	0.63694 (14)	0.09160 (9)	0.0497 (3)
N21	0.92041 (16)	0.29721 (15)	0.39635 (8)	0.0494 (3)
N22	0.8731 (3)	0.0080 (2)	0.25846 (16)	0.1020 (7)
N12A	0.4599 (15)	0.972 (4)	0.222 (2)	0.100 (4)	0.66 (8)
N12B	0.466 (4)	0.916 (6)	0.252 (3)	0.085 (6)	0.34 (8)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C11	0.0471 (8)	0.0391 (7)	0.0555 (8)	−0.0166 (6)	−0.0054 (6)	−0.0037 (6)
C16	0.0411 (7)	0.0434 (7)	0.0506 (8)	−0.0148 (6)	0.0017 (6)	−0.0064 (6)
C10	0.0539 (8)	0.0439 (8)	0.0529 (9)	−0.0215 (6)	−0.0049 (6)	−0.0009 (6)
C17	0.0550 (8)	0.0447 (8)	0.0597 (9)	−0.0227 (7)	−0.0037 (7)	0.0018 (7)
C18	0.0611 (9)	0.0469 (8)	0.0728 (10)	−0.0233 (7)	−0.0141 (8)	−0.0108 (7)
C15	0.0567 (9)	0.0693 (10)	0.0519 (9)	−0.0200 (8)	0.0035 (7)	−0.0102 (8)
C14	0.0631 (10)	0.0669 (11)	0.0705 (11)	−0.0135 (8)	−0.0062 (8)	−0.0307 (9)
C19	0.0700 (12)	0.0728 (12)	0.0872 (14)	−0.0258 (10)	−0.0134 (10)	−0.0353 (10)
C12	0.0875 (12)	0.0422 (8)	0.0784 (12)	−0.0294 (8)	−0.0189 (9)	0.0008 (8)
C13	0.0835 (12)	0.0453 (9)	0.1006 (15)	−0.0209 (9)	−0.0214 (11)	−0.0213 (9)
C20	0.0446 (7)	0.0517 (8)	0.0462 (8)	−0.0201 (6)	−0.0124 (6)	0.0007 (6)
C26	0.0418 (7)	0.0632 (9)	0.0449 (8)	−0.0185 (7)	−0.0123 (6)	0.0011 (7)
C21	0.0432 (7)	0.0540 (8)	0.0462 (8)	−0.0167 (6)	−0.0127 (6)	−0.0035 (6)
C27	0.0455 (8)	0.0578 (9)	0.0532 (8)	−0.0209 (7)	−0.0143 (6)	0.0073 (7)
C28	0.0518 (9)	0.0554 (9)	0.0701 (10)	−0.0151 (7)	−0.0088 (8)	−0.0125 (8)
C22	0.0573 (9)	0.0558 (9)	0.0674 (10)	−0.0164 (7)	−0.0166 (8)	−0.0072 (8)
C29	0.0628 (10)	0.0485 (9)	0.0830 (12)	−0.0116 (8)	−0.0123 (9)	−0.0185 (8)
C23	0.0590 (10)	0.0699 (11)	0.0766 (12)	−0.0041 (8)	−0.0181 (9)	−0.0257 (10)
C25	0.0492 (9)	0.0898 (13)	0.0496 (9)	−0.0219 (8)	−0.0069 (7)	−0.0001 (8)
C24	0.0517 (9)	0.0973 (15)	0.0572 (10)	−0.0114 (9)	−0.0049 (8)	−0.0202 (10)
O11	0.1064 (10)	0.0764 (8)	0.0524 (7)	−0.0494 (8)	−0.0150 (6)	0.0068 (6)
O12	0.1289 (12)	0.0668 (8)	0.0810 (9)	−0.0601 (8)	−0.0181 (8)	0.0195 (7)
O20	0.0651 (7)	0.0686 (7)	0.0530 (6)	−0.0320 (6)	−0.0011 (5)	0.0014 (5)
O21	0.0695 (7)	0.0627 (7)	0.0869 (9)	−0.0291 (6)	−0.0133 (6)	0.0184 (6)
N11	0.0584 (7)	0.0396 (6)	0.0556 (7)	−0.0229 (5)	−0.0072 (6)	−0.0052 (5)
N21	0.0499 (7)	0.0496 (7)	0.0498 (7)	−0.0186 (5)	−0.0072 (5)	−0.0065 (5)
N22	0.0928 (13)	0.0766 (11)	0.1438 (18)	−0.0253 (10)	−0.0265 (12)	−0.0498 (12)
N12A	0.078 (2)	0.098 (7)	0.114 (8)	−0.013 (4)	−0.013 (4)	−0.048 (7)
N12B	0.079 (5)	0.081 (10)	0.088 (10)	−0.020 (6)	0.005 (5)	−0.040 (7)

Geometric parameters (Å, º) top

C11—C12	1.376 (2)	C20—N21	1.3944 (18)
C11—C16	1.381 (2)	C20—C21	1.481 (2)
C11—C10	1.480 (2)	C26—C21	1.380 (2)
C16—C15	1.378 (2)	C26—C25	1.381 (2)
C16—C17	1.482 (2)	C26—C27	1.482 (2)
C10—O11	1.2052 (18)	C21—C22	1.382 (2)
C10—N11	1.3903 (18)	C27—O21	1.2066 (17)
C17—O12	1.1989 (18)	C27—N21	1.3958 (19)
C17—N11	1.395 (2)	C28—N21	1.4445 (19)
C18—N11	1.4511 (18)	C28—C29	1.460 (2)
C18—C19	1.458 (2)	C28—H28A	0.9700
C18—H18A	0.9700	C28—H28B	0.9700
C18—H18B	0.9700	C22—C23	1.388 (2)
C15—C14	1.380 (2)	C22—H22	0.9300
C15—H15	0.9300	C29—N22	1.125 (2)
C14—C13	1.369 (3)	C23—C24	1.372 (3)
C14—H14	0.9300	C23—H23	0.9300
C12—C13	1.383 (3)	C25—C24	1.383 (3)
C12—H12	0.9300	C25—H25	0.9300
C13—H13	0.9300	C24—H24	0.9300
C20—O20	1.2021 (17)

C12—C11—C16	120.65 (14)	C21—C26—C27	108.31 (13)
C12—C11—C10	130.71 (15)	C25—C26—C27	130.42 (15)
C16—C11—C10	108.64 (12)	C26—C21—C22	121.60 (14)
C15—C16—C11	121.80 (13)	C26—C21—C20	108.40 (13)
C15—C16—C17	130.20 (14)	C22—C21—C20	129.99 (14)
C11—C16—C17	108.00 (13)	O21—C27—N21	124.00 (15)
O11—C10—N11	123.96 (14)	O21—C27—C26	130.39 (15)
O11—C10—C11	130.57 (14)	N21—C27—C26	105.61 (12)
N11—C10—C11	105.46 (12)	N21—C28—C29	112.91 (13)
O12—C17—N11	124.60 (15)	N21—C28—H28A	109.0
O12—C17—C16	129.75 (15)	C29—C28—H28A	109.0
N11—C17—C16	105.63 (12)	N21—C28—H28B	109.0
N11—C18—C19	111.30 (13)	C29—C28—H28B	109.0
N11—C18—H18A	109.4	H28A—C28—H28B	107.8
C19—C18—H18A	109.4	C21—C22—C23	116.75 (17)
N11—C18—H18B	109.4	C21—C22—H22	121.6
C19—C18—H18B	109.4	C23—C22—H22	121.6
H18A—C18—H18B	108.0	N22—C29—C28	177.51 (18)
C16—C15—C14	117.07 (16)	C24—C23—C22	121.71 (17)
C16—C15—H15	121.5	C24—C23—H23	119.1
C14—C15—H15	121.5	C22—C23—H23	119.1
C13—C14—C15	121.47 (16)	C26—C25—C24	117.30 (17)
C13—C14—H14	119.3	C26—C25—H25	121.4
C15—C14—H14	119.3	C24—C25—H25	121.4
C11—C12—C13	117.66 (16)	C23—C24—C25	121.36 (16)
C11—C12—H12	121.2	C23—C24—H24	119.3
C13—C12—H12	121.2	C25—C24—H24	119.3
C14—C13—C12	121.34 (16)	C10—N11—C17	112.21 (12)
C14—C13—H13	119.3	C10—N11—C18	123.66 (13)
C12—C13—H13	119.3	C17—N11—C18	124.11 (12)
O20—C20—N21	124.84 (14)	C20—N21—C27	112.00 (12)
O20—C20—C21	129.50 (14)	C20—N21—C28	123.18 (12)
N21—C20—C21	105.65 (12)	C27—N21—C28	124.49 (13)
C21—C26—C25	121.28 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···O12ⁱ	0.93	2.51	3.386 (2)	158
C15—H15···O20ⁱⁱ	0.93	2.45	3.144 (2)	132
C18—H18B···O20	0.97	2.42	3.372 (2)	167
C28—H28A···O21ⁱⁱⁱ	0.97	2.39	3.298 (2)	156

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

Experimental details

Crystal data
Chemical formula	C₁₀H₆N₂O₂
M_r	186.17
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	8.0960 (2), 8.4371 (2), 14.3118 (3)
α, β, γ (°)	85.072 (1), 79.272 (1), 68.421 (1)
V (Å³)	893.02 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.25 × 0.24 × 0.16

Data collection
Diffractometer	Bruker APEXII CCD detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	18332, 3906, 2885
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.128, 1.05
No. of reflections	3906
No. of parameters	267
No. of restraints	6
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.20

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···O12ⁱ	0.93	2.51	3.386 (2)	158
C15—H15···O20ⁱⁱ	0.93	2.45	3.144 (2)	132
C18—H18B···O20	0.97	2.42	3.372 (2)	167
C28—H28A···O21ⁱⁱⁱ	0.97	2.39	3.298 (2)	156

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

Acknowledgements

The authors thank the CNRST, Morocco, for making this work possible.

References

Berghmans, S., Hunt, J., Roach, A. & Goldsmith, P. (2007). Epilepsy Res. 75, 18–28. Web of Science CrossRef PubMed CAS Google Scholar
Bruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Hashimoto, Y., Ohashi, R., Kurosawa, Y., Minami, K., Kaji, H., Hayashida, K., Narita, H. & Murata, S. (1998). J. Cardiovasc. Pharm. 31, 568–575. Web of Science CrossRef CAS Google Scholar
Lim, S. J., Sunohara, Y. & Matsumoto, H. (2007). J. Pestic. Sci. 32, 249–254. Web of Science CrossRef CAS Google Scholar
Muraglia, E., Kinzel, O. D., Laufer, R., Miller, M. D., Moyer, G., Munshi, V., Orvieto, F., Palumbi, M. C., Pescatore, G., Rowley, M., Williams, P. D. & Summa, V. (2006). Bioorg. Med. Chem. Lett. 16, 2748–2752. Web of Science CrossRef PubMed CAS Google Scholar
Schocken, M. J., Creekmore, R. W., Theodoridis, G., Nystrom, G. J. & Robinson, R. A. (1989). Appl. Environ. Microbiol. 55, 1220–2122. PubMed CAS Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Shih, T. L., Candelore, M. R., Cascieri, M. A., Chiu, S.-H. L., Colwell, L. F. Jr, Deng, L., Feeney, W. P., Forrest, M. J., Hom, G. J., MacIntyre, D. E., Miller, R. R., Stearns, R. A., Strader, C. D., Tota, L., Wyvratt, M. J., Fisher, M. H. & Weber, A. E. (1999). Bioorg. Med. Chem. Lett. 9, 1251–1254. Web of Science CrossRef PubMed Google Scholar
Singh, H., Chawla, A. S., Kapoor, V. K., Paul, D. & Malhotra, R. K. (1980). Prog. Med. Chem. 17, 151–183. CrossRef CAS PubMed Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Tamura, Y. F., Watanabe, F., Nakatani, T., Yasui, K., Fuji, M., Komurasaki, T., Tsuzuki, H., Maekawa, R., Yoshioka, T., Kawada, K., Sugita, K. & Ohtani, M. (1998). J. Med. Chem. 41, 640–649. Web of Science CrossRef CAS PubMed Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar
Yanagi, A. (2001). Pflanzenschutz Nachr. Bayer. 54, 1–11. Google Scholar