1-Allyl-3-benzyl-1H-benzimidazol-2(3H)-one

Kandri Rodi, Y.; Haoudi, A.; Capet, F.; Mazzah, A.; Essassi, E.M.; El Ammari, L.

doi:10.1107/S1600536813023568

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 69| Part 9| September 2013| Pages o1477-o1478

doi:10.1107/S1600536813023568

Open

access

1-Allyl-3-benzyl-1H-benzimidazol-2(3H)-one

Youssef Kandri Rodi,^a Amal Haoudi,^a ^* Frédéric Capet,^b Ahmed Mazzah,^c El Mokhtar Essassi ^d and Lahcen El Ammari ^e

^aLaboratoire de Chimie Organique Appliquée, Université Sidi Mohamed Ben Abdallah, Faculté des Sciences et Techniques, Route d'Immouzzer, BP 2202 Fès, Morocco, ^bUnité de Catalyse et de Chimie du Solide (UCCS), UMR 8181, Ecole Nationale Supérieure de Chimie de Lille, France, ^cUSR 3290 Miniaturisation pour l'Analyse, la Synthèse et la Protéomique, 59655 Villeneuve d'Ascq Cedex, Université Lille 1, France, ^dLaboratoire de Chimie Organique Hétérocyclique, URAC 21, Pôle de Compétences Pharmacochimie, Université Mohammed V-Agdal, BP 1014 Avenue, Ibn Batouta, Rabat, Morocco, and ^eLaboratoire de Chimie du Solide Appliquée, Faculté des Sciences, Université Mohammed V-Agdal, Avenue Ibn Battouta, BP 1014, Rabat, Morocco
^*Correspondence e-mail: amal_haoudi@yahoo.fr

(Received 5 August 2013; accepted 21 August 2013; online 31 August 2013)

In the title compound, C₁₇H₁₆N₂O, the fused benzimidazol-2(3H)-one system is essentially planar, the largest deviation from the mean plane being 0.006 (2) Å for the carbonyl C atom. Its mean plane is almost perpendicular to the benzyl plane and to the allyl group, making dihedral angles of 80.6 (1) and 77.4 (3)°, respectively. The benzyl group and the allyl subsituent lie on opposite sides of the fused ring system. In the crystal, molecules are linked by bifurcated C—H⋯O hydrogen bonds in which the carbonyl O atom acts as accepter to two aromatic C—H groups, forming a two-dimensional network parallel to (001).

Related literature

For the biological activity of benzimidazole derivatives, see: Gravatt et al. (1994 ); Soderlind et al. (1999 ); Bouwman et al. (1990 ) and for potential applications in the treatment of some diseases, see: Zhu et al. (2008 ); Ogino et al. (2008 ); Shah et al. (2008 ). For their use as intermediates in chemical synthesis, see: Bai et al. (2001 ). For similar compounds, see: Belaziz et al. (2012 , 2013 ).

Experimental

Crystal data

C₁₇H₁₆N₂O
M_r = 264.32
Triclinic, $[P \overline 1]$
a = 9.0667 (2) Å
b = 9.3922 (2) Å
c = 9.6486 (2) Å
α = 94.218 (1)°
β = 113.543 (1)°
γ = 106.265 (1)°
V = 706.87 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 296 K
0.43 × 0.20 × 0.16 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.967, T_max = 0.988
12670 measured reflections
3494 independent reflections
2573 reflections with I > 2σ(I)
R_int = 0.021

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.141
S = 1.06
3494 reflections
181 parameters
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.15 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O1ⁱ	0.93	2.48	3.405 (2)	173
C14—H14⋯O1ⁱⁱ	0.93	2.56	3.330 (2)	141
Symmetry codes: (i) x-1, y, z; (ii) x, y+1, z.

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT-Plus (Bruker, 2009); data reduction: SAINT-Plus; 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, 2012 ); software used to prepare material for publication: PLATON (Spek, 2009 ) and publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablock I. DOI: 10.1107/S1600536813023568/im2438sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813023568/im2438Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813023568/im2438Isup3.cml

checkCIF report

Comment top

Functionalized benzimidazoles represent an important class of N-containing heterocyclic compounds and have received considerable attention in recent times because of their applications as antiulcers, antihypertensives, antivirals, antifungals, anticancers and antihistamines among others (Gravatt et al., 1994; Soderlind et al., 1999). They are also important intermediates in many organic reactions (Bai et al., 2001) and act as ligands to transition metals for modelling biological systems (Bouwman et al., 1990). In addition, the treatment potency of benzimidazoles in diseases such as ischemia–reperfusion injury (Zhu et al., 2008), hypertension (Ogino et al., 2008), obesity (Shah et al., 2008) etc. have been recently reported.

In continuation of our research work devoted to the development of substituted benzimidazol-2-one derivatives (Belaziz et al., 2012, 2013), we reported a synthesis of new benzimidazol-2-one derivative differently substituted by action of allylbromide with 1-benzyl -1H-benzo[d]imidazol-2(3H)-one in the presence of a catalytic quantity of tetra-n-butylammonium bromide under mild conditions to obtain disubstituted compound (Scheme 1).

The molecule of title compound, 1-allyl-3-(benzyl)-1H-benzo[d]imidazol-2(3H)- one, is built up from two fused five- and six-membered rings linked to a benzyl substituent and an allyl group as shown in Fig. 1. The fused rings system (N1, N2, C1-C7) is essentially planar with the largest deviation from the mean plane being -0.006 (2) A° at C5 atom. The benzyl group and the allyl group are almost perpendicular to the benzo[d]imidazol-2(3H)-one as indicated by the dihedral angles of 80.6 (1) and 77.4 (3) °, respectively.

In the crystal, the molecules are linked by C3–H3···O1 and C14–H14···O1 hydrogen bonds in the way to build two-dimensional network as shown in Fig. 2 and Table 2.

Related literature top

For the biological activity of benzimidazole derivatives, see: Gravatt et al. (1994); Soderlind et al. (1999); Bouwman et al. (1990) and for potential applications in the treatment of some diseases, see: Zhu et al. (2008); Ogino et al. (2008); Shah et al. (2008). For their use as intermediates in chemical synthesis, see: Bai et al. (2001). For similar compounds, see: Belaziz et al. (2012, 2013).

Experimental top

To 1H-benzo[d]imidazol-2(3H)-one (0.2 g, 1.49 mmol), potassium carbonate (0.41 g, 2.98 mmol) and tetra-n-butylammonium bromide (0.05 g, 0.15 mmol) in DMF (20 ml) was added benzylchloride (0.22 g, 1.79 mmol). Stirring was continued at room temperature for 6 h. The resulting salt was removed by filtration and the filtrate concentrated under reduced pressure. The residue was separated by chromatography on a column of silica gel with ethyl acetate/hexane (1/2) as eluent. The compound was recrystallized from ethanol to give colorless crystals. To the compound obtained (1-benzyl-benzimidazol-2-one (0.15 g, 0.67 mmol) was added allylbromide (0.10 g, 0.87 mmol) in DMF (10 ml), and potassium carbonate (0.18 g, 1.33 mmol) and tetra-n-butylammonium bromide (0.02 g, 0.07 mmol). Stirring was continued at room temperature for 12 h. The formed salt was removed by filtration and the filtrate concentrated under reduced pressure. The residue was separated by chromatography on a column of silica gel with ethyl acetate/hexane (1/1) as eluent (yield 82%, based on the intermediate). The title compound was recrystallized from dichloromethane/hexane to give colourless crystals.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT-Plus (Bruker, 2009); data reduction: SAINT-Plus (Bruker, 2009); 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, 2012); software used to prepare material for publication: PLATON (Spek, 2009) and publCIF (Westrip, 2010).

Figures top

	Fig. 1. : Molecular structure of the title compound with the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are represented as small circles.
	Fig. 2. : Intermolecular interactions in the title compound building a two-dimensional network. Hydrogen bonds are shown as dashed blue lines.

1-Allyl-3-benzyl-1H-benzimidazol-2(3H)-one top

Crystal data top

C₁₇H₁₆N₂O	Z = 2
M_r = 264.32	F(000) = 280
Triclinic, P1	D_x = 1.242 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.0667 (2) Å	Cell parameters from 3494 reflections
b = 9.3922 (2) Å	θ = 2.3–28.3°
c = 9.6486 (2) Å	µ = 0.08 mm⁻¹
α = 94.218 (1)°	T = 296 K
β = 113.543 (1)°	Irregular shape, colourless
γ = 106.265 (1)°	0.43 × 0.20 × 0.16 mm
V = 706.87 (3) Å³

Data collection top

Bruker APEXII CCD diffractometer	3494 independent reflections
Radiation source: microfocus source	2573 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.021
ϕ and ω scans	θ_max = 28.3°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −12→12
T_min = 0.967, T_max = 0.988	k = −12→12
12670 measured reflections	l = −12→12

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.141	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0617P)² + 0.1232P] where P = (F_o² + 2F_c²)/3
3494 reflections	(Δ/σ)_max < 0.001
181 parameters	Δρ_max = 0.18 e Å⁻³
0 restraints	Δρ_min = −0.15 e Å⁻³

Crystal data top

C₁₇H₁₆N₂O	γ = 106.265 (1)°
M_r = 264.32	V = 706.87 (3) Å³
Triclinic, P1	Z = 2
a = 9.0667 (2) Å	Mo Kα radiation
b = 9.3922 (2) Å	µ = 0.08 mm⁻¹
c = 9.6486 (2) Å	T = 296 K
α = 94.218 (1)°	0.43 × 0.20 × 0.16 mm
β = 113.543 (1)°

Data collection top

Bruker APEXII CCD diffractometer	3494 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	2573 reflections with I > 2σ(I)
T_min = 0.967, T_max = 0.988	R_int = 0.021
12670 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.141	H-atom parameters constrained
S = 1.06	Δρ_max = 0.18 e Å⁻³
3494 reflections	Δρ_min = −0.15 e Å⁻³
181 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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
C1	0.08458 (17)	0.53012 (15)	0.75007 (15)	0.0503 (3)
C2	−0.0580 (2)	0.4975 (2)	0.77755 (18)	0.0652 (4)
H2	−0.0800	0.4235	0.8325	0.078*
C3	−0.1663 (2)	0.5780 (2)	0.7211 (2)	0.0785 (5)
H3	−0.2638	0.5575	0.7376	0.094*
C4	−0.1336 (2)	0.6887 (2)	0.6404 (2)	0.0778 (5)
H4	−0.2098	0.7410	0.6034	0.093*
C5	0.0111 (2)	0.72378 (18)	0.61297 (19)	0.0636 (4)
H5	0.0338	0.7989	0.5594	0.076*
C6	0.11833 (17)	0.64210 (14)	0.66878 (15)	0.0484 (3)
C7	0.33127 (18)	0.54248 (15)	0.73733 (17)	0.0524 (3)
C8	0.2415 (2)	0.35712 (18)	0.88407 (19)	0.0710 (5)
H8A	0.2268	0.3845	0.9755	0.085*
H8B	0.3582	0.3588	0.9181	0.085*
C9	0.1241 (3)	0.20112 (19)	0.8030 (2)	0.0777 (5)
H9	0.1257	0.1609	0.7128	0.093*
C10	0.0209 (3)	0.1174 (3)	0.8466 (4)	0.1171 (9)
H10A	0.0154	0.1535	0.9362	0.141*
H10B	−0.0490	0.0201	0.7889	0.141*
C11	0.3572 (2)	0.74859 (15)	0.59174 (18)	0.0576 (4)
H11A	0.2751	0.7508	0.4904	0.069*
H11B	0.4401	0.7099	0.5778	0.069*
C12	0.44798 (18)	0.90823 (15)	0.68814 (16)	0.0507 (3)
C13	0.4105 (2)	1.02876 (17)	0.6275 (2)	0.0635 (4)
H13	0.3285	1.0118	0.5261	0.076*
C14	0.4935 (3)	1.17505 (18)	0.7159 (3)	0.0762 (5)
H14	0.4671	1.2557	0.6738	0.091*
C15	0.6135 (3)	1.2009 (2)	0.8642 (3)	0.0798 (6)
H15	0.6686	1.2991	0.9236	0.096*
C16	0.6534 (3)	1.0830 (2)	0.9259 (2)	0.0854 (6)
H16	0.7360	1.1011	1.0273	0.102*
C17	0.5712 (2)	0.93636 (19)	0.8379 (2)	0.0709 (5)
H17	0.5994	0.8565	0.8803	0.085*
N1	0.21567 (15)	0.47062 (13)	0.79022 (14)	0.0546 (3)
N2	0.26911 (15)	0.64676 (12)	0.66155 (14)	0.0504 (3)
O1	0.46264 (14)	0.51931 (12)	0.75495 (15)	0.0703 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0468 (7)	0.0456 (7)	0.0449 (7)	0.0041 (6)	0.0168 (6)	−0.0037 (5)
C2	0.0565 (9)	0.0695 (10)	0.0581 (9)	0.0033 (7)	0.0286 (7)	−0.0032 (7)
C3	0.0530 (9)	0.0892 (13)	0.0808 (12)	0.0110 (9)	0.0317 (9)	−0.0143 (10)
C4	0.0553 (10)	0.0799 (12)	0.0836 (12)	0.0281 (9)	0.0168 (9)	−0.0067 (10)
C5	0.0600 (9)	0.0563 (9)	0.0633 (9)	0.0209 (7)	0.0168 (7)	0.0043 (7)
C6	0.0462 (7)	0.0418 (6)	0.0467 (7)	0.0087 (5)	0.0164 (6)	−0.0024 (5)
C7	0.0488 (8)	0.0387 (6)	0.0586 (8)	0.0074 (6)	0.0193 (6)	0.0016 (6)
C8	0.0755 (11)	0.0578 (9)	0.0593 (9)	0.0110 (8)	0.0165 (8)	0.0192 (7)
C9	0.0935 (13)	0.0534 (9)	0.0736 (11)	0.0171 (9)	0.0287 (10)	0.0196 (8)
C10	0.120 (2)	0.0697 (13)	0.162 (2)	0.0150 (13)	0.0698 (18)	0.0428 (15)
C11	0.0682 (9)	0.0451 (7)	0.0594 (8)	0.0098 (7)	0.0352 (7)	0.0057 (6)
C12	0.0544 (8)	0.0424 (7)	0.0567 (8)	0.0078 (6)	0.0322 (7)	0.0066 (6)
C13	0.0704 (10)	0.0526 (8)	0.0670 (9)	0.0180 (7)	0.0316 (8)	0.0126 (7)
C14	0.0904 (13)	0.0455 (8)	0.1024 (15)	0.0198 (8)	0.0541 (12)	0.0139 (9)
C15	0.0848 (13)	0.0490 (9)	0.0948 (14)	−0.0039 (8)	0.0512 (11)	−0.0105 (9)
C16	0.0789 (12)	0.0732 (12)	0.0676 (11)	−0.0026 (9)	0.0191 (9)	−0.0043 (9)
C17	0.0726 (11)	0.0556 (9)	0.0693 (10)	0.0109 (8)	0.0237 (9)	0.0128 (8)
N1	0.0539 (7)	0.0447 (6)	0.0559 (7)	0.0095 (5)	0.0199 (5)	0.0109 (5)
N2	0.0508 (6)	0.0381 (5)	0.0604 (7)	0.0103 (5)	0.0262 (5)	0.0074 (5)
O1	0.0533 (6)	0.0580 (6)	0.0960 (9)	0.0210 (5)	0.0287 (6)	0.0116 (6)

Geometric parameters (Å, º) top

C1—C2	1.378 (2)	C9—C10	1.274 (3)
C1—N1	1.3824 (19)	C9—H9	0.9300
C1—C6	1.396 (2)	C10—H10A	0.9300
C2—C3	1.371 (3)	C10—H10B	0.9300
C2—H2	0.9300	C11—N2	1.4503 (18)
C3—C4	1.381 (3)	C11—C12	1.5109 (19)
C3—H3	0.9300	C11—H11A	0.9700
C4—C5	1.396 (3)	C11—H11B	0.9700
C4—H4	0.9300	C12—C13	1.376 (2)
C5—C6	1.373 (2)	C12—C17	1.377 (2)
C5—H5	0.9300	C13—C14	1.385 (2)
C6—N2	1.3853 (18)	C13—H13	0.9300
C7—O1	1.2181 (17)	C14—C15	1.359 (3)
C7—N1	1.3771 (19)	C14—H14	0.9300
C7—N2	1.3773 (18)	C15—C16	1.364 (3)
C8—N1	1.4572 (19)	C15—H15	0.9300
C8—C9	1.478 (2)	C16—C17	1.386 (2)
C8—H8A	0.9700	C16—H16	0.9300
C8—H8B	0.9700	C17—H17	0.9300

C2—C1—N1	131.78 (15)	H10A—C10—H10B	120.0
C2—C1—C6	121.12 (15)	N2—C11—C12	112.61 (11)
N1—C1—C6	107.10 (12)	N2—C11—H11A	109.1
C3—C2—C1	117.73 (17)	C12—C11—H11A	109.1
C3—C2—H2	121.1	N2—C11—H11B	109.1
C1—C2—H2	121.1	C12—C11—H11B	109.1
C2—C3—C4	121.36 (17)	H11A—C11—H11B	107.8
C2—C3—H3	119.3	C13—C12—C17	118.60 (14)
C4—C3—H3	119.3	C13—C12—C11	120.70 (14)
C3—C4—C5	121.50 (17)	C17—C12—C11	120.70 (14)
C3—C4—H4	119.2	C12—C13—C14	120.70 (17)
C5—C4—H4	119.2	C12—C13—H13	119.6
C6—C5—C4	116.84 (17)	C14—C13—H13	119.6
C6—C5—H5	121.6	C15—C14—C13	120.04 (17)
C4—C5—H5	121.6	C15—C14—H14	120.0
C5—C6—N2	131.80 (14)	C13—C14—H14	120.0
C5—C6—C1	121.45 (14)	C14—C15—C16	120.13 (16)
N2—C6—C1	106.75 (12)	C14—C15—H15	119.9
O1—C7—N1	126.96 (14)	C16—C15—H15	119.9
O1—C7—N2	126.92 (14)	C15—C16—C17	120.12 (18)
N1—C7—N2	106.13 (12)	C15—C16—H16	119.9
N1—C8—C9	114.03 (14)	C17—C16—H16	119.9
N1—C8—H8A	108.7	C12—C17—C16	120.40 (17)
C9—C8—H8A	108.7	C12—C17—H17	119.8
N1—C8—H8B	108.7	C16—C17—H17	119.8
C9—C8—H8B	108.7	C7—N1—C1	109.97 (12)
H8A—C8—H8B	107.6	C7—N1—C8	122.70 (14)
C10—C9—C8	125.3 (2)	C1—N1—C8	127.18 (14)
C10—C9—H9	117.4	C7—N2—C6	110.04 (12)
C8—C9—H9	117.4	C7—N2—C11	123.15 (12)
C9—C10—H10A	120.0	C6—N2—C11	126.76 (12)
C9—C10—H10B	120.0

N1—C1—C2—C3	−179.88 (14)	C15—C16—C17—C12	−0.5 (3)
C6—C1—C2—C3	0.6 (2)	O1—C7—N1—C1	178.76 (14)
C1—C2—C3—C4	−0.4 (2)	N2—C7—N1—C1	−0.76 (15)
C2—C3—C4—C5	−0.1 (3)	O1—C7—N1—C8	2.9 (2)
C3—C4—C5—C6	0.6 (2)	N2—C7—N1—C8	−176.64 (12)
C4—C5—C6—N2	179.56 (14)	C2—C1—N1—C7	−179.26 (14)
C4—C5—C6—C1	−0.5 (2)	C6—C1—N1—C7	0.34 (15)
C2—C1—C6—C5	−0.1 (2)	C2—C1—N1—C8	−3.6 (2)
N1—C1—C6—C5	−179.75 (12)	C6—C1—N1—C8	175.99 (13)
C2—C1—C6—N2	179.87 (12)	C9—C8—N1—C7	−109.85 (18)
N1—C1—C6—N2	0.22 (14)	C9—C8—N1—C1	75.0 (2)
N1—C8—C9—C10	−121.4 (2)	O1—C7—N2—C6	−178.62 (14)
N2—C11—C12—C13	−122.16 (15)	N1—C7—N2—C6	0.90 (15)
N2—C11—C12—C17	58.5 (2)	O1—C7—N2—C11	−1.0 (2)
C17—C12—C13—C14	−0.7 (2)	N1—C7—N2—C11	178.55 (11)
C11—C12—C13—C14	179.94 (15)	C5—C6—N2—C7	179.26 (14)
C12—C13—C14—C15	0.0 (3)	C1—C6—N2—C7	−0.70 (14)
C13—C14—C15—C16	0.5 (3)	C5—C6—N2—C11	1.7 (2)
C14—C15—C16—C17	−0.3 (3)	C1—C6—N2—C11	−178.24 (12)
C13—C12—C17—C16	0.9 (3)	C12—C11—N2—C7	−102.99 (15)
C11—C12—C17—C16	−179.72 (16)	C12—C11—N2—C6	74.25 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O1ⁱ	0.93	2.48	3.405 (2)	173
C14—H14···O1ⁱⁱ	0.93	2.56	3.330 (2)	141

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O1ⁱ	0.93	2.48	3.405 (2)	172.9
C14—H14···O1ⁱⁱ	0.93	2.56	3.330 (2)	140.7

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

References

Bai, Y., Lu, J., Shi, Z. & Yang, B. (2001). Synlett, 12, 544–546. Google Scholar
Belaziz, D., Kandri Rodi, Y., Kandri Rodi, A., Essassi, E. M., Saadi, M. & El Ammari, L. (2013). Acta Cryst. E69, o641–o642. CSD CrossRef CAS IUCr Journals Google Scholar
Belaziz, D., Kandri Rodi, Y., Ouazzani Chahdi, F., Essassi, E. M., Saadi, M. & El Ammari, L. (2012). Acta Cryst. E68, o3212. CSD CrossRef IUCr Journals Google Scholar
Bouwman, E., Driessen, W. L. & Reedjik, J. (1990). Coord. Chem. Rev. 104, 143–172. CrossRef CAS Web of Science Google Scholar
Bruker (2009). APEX2, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Gravatt, G. L., Baguley, B. C., Wilson, W. R. & Denny, W. A. (1994). J. Med. Chem. 37, 4338–4345. CrossRef CAS PubMed Web of Science Google Scholar
Ogino, Y., Ohtake, N., Nagae, Y., Matsuda, K., Moriya, M., Suga, T., Ishikawa, M., Kanesaka, M., Mitobe, Y., Ito, J., Kanno, T., Ishiara, A., Iwaasa, H., Ohe, T., Kanatani, A. & Fukami, T. (2008). Bioorg. Med. Chem. Lett. 18, 5010–5014. Web of Science CrossRef PubMed CAS Google Scholar
Shah, D. I., Sharma, M., Bansal, Y., Bansal, G. & Singh, M. (2008). Eur. J. Med. Chem. 43, 1808–1812. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Soderlind, K. J., Gorodetsky, B., Singh, A. K., Bachur, N. R., Miller, G. G. & Lown, J. W. (1999). Anticancer Drug Des. 14, 19–36. Web of Science PubMed CAS Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zhu, G.-D., Gandhi, V. B., Gong, J., Thomas, S., Luo, Y., Liu, X., Shi, Y., Klinghofer, V., Johnson, E. F., Frost, D., Donawho, C., Jarvis, K., Bouska, J., Marsh, K. C., Rosenberg, S. H., Giranda, V. L. & Penning, T. D. (2008). Bioorg. Med. Chem. Lett. 18, 3955–3958. Web of Science CrossRef PubMed CAS Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 69| Part 9| September 2013| Pages o1477-o1478

doi:10.1107/S1600536813023568

Open

access