1-(Prop-2-en-1-yl)-3-{[3-(pyridin-4-yl)-4,5-di­hydro­isoxazol-5-yl]meth­yl}-1H-anthra[1,2-d]imidazole-2,6,11(3H)-trione

Afrakssou, Z.; Kandri Rodia, Y.; Capet, F.; Essassi, E.M.; Rolando, C.; El Ammari, L.

doi:10.1107/S160053681301369X

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 69| Part 6| June 2013| Pages o945-o946

doi:10.1107/S160053681301369X

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1-(Prop-2-en-1-yl)-3-{[3-(pyridin-4-yl)-4,5-dihydroisoxazol-5-yl]methyl}-1H-anthra[1,2-d]imidazole-2,6,11(3H)-trione

Zahra Afrakssou,^a ^* Youssef Kandri Rodia,^a Frédéric Capet,^b El Mokhtar Essassi,^c Christian Rolando ^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, ^cLaboratoire de Chimie Organique Hétérocyclique, URAC 21, Pôle de Compétences Pharmacochimie, Université Mohammed V-Agdal, BP 1014, Avenue Ibn Batouta, Rabat , Morocco, ^dUSR 3290 Miniaturisation pour l'Analyse, la Synthèse et la Protéomique, 59655 Villeneuve d'Ascq Cedex, Université Lille 1, France, and ^eLaboratoire de Chimie du Solide Appliquée, Faculté des Sciences, Université Mohammed V-Agdal, Avenue Ibn Battouta, BP 1014, Rabat, Morocco
^*Correspondence e-mail: afrassou@yahoo.fr

(Received 13 May 2013; accepted 17 May 2013; online 22 May 2013)

The fused five- and three six-membered rings of the anthra[1,2-d]imidazoletrione part of the title compound, C₂₇H₂₀N₄O₄, show two different substituents at the imidazole N atoms, viz. an allyl group and a [3-(pyridin-4-yl)-4,5-dihydroisoxazol-5-yl]methyl group. The fused-ring system is approximately planar [r.m.s. deviation = 0.232 (2) Å], but is slightly buckled along the common edge of the two pairs of adjacent rings, with a dihedral angle between them of 11.17 (6)°. The isoxazole ring makes dihedral angles of 27.2 (2) and 12.7 (2)° with the imidazole and pyridine rings, respectively. Weak C—H⋯O and C—H⋯N hydrogen bonds ensure the cohesion of the crystal structure, forming a three-dimensional network.

Related literature

For the use of anthraquinone as an organic redox mediator, see: Campos-Martin et al. (2006 ); Harish et al. (2009 ); Jürmann et al. (2007 ); Manisankar & Gomathi (2005 ). For the biological activity of anthraquinone derivatives, see: Henderson et al. (1998 ); Barasch et al. (1999 ); Dou et al. (2009 ). For background to pH sensor applications, see: Wong et al. (2004 ); Lafitte et al. (2008 ); Wildgoose et al. (2003 ). For similar compounds, see: Afrakssou et al. (2010 , 2011 ).

Experimental

Crystal data

C₂₇H₂₀N₄O₄
M_r = 464.47
Triclinic, $[P \overline 1]$
a = 8.0930 (2) Å
b = 12.1191 (3) Å
c = 12.2743 (2) Å
α = 87.109 (1)°
β = 73.612 (1)°
γ = 72.283 (1)°
V = 1099.35 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 296 K
0.14 × 0.10 × 0.08 mm

Data collection

Bruker APEXII CCD diffractometer
36799 measured reflections
5659 independent reflections
3900 reflections with I > 2σ(I)
R_int = 0.031

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.148
S = 1.02
5659 reflections
316 parameters
H-atom parameters constrained
Δρ_max = 0.37 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
C3—H3⋯N3ⁱ	0.93	2.58	3.471 (2)	160
C3—H3⋯O4ⁱ	0.93	2.67	3.470 (2)	145
C19—H19A⋯O3ⁱⁱ	0.97	2.56	3.3356 (19)	137
C21—H21A⋯O3ⁱⁱ	0.97	2.45	3.350 (2)	154
Symmetry codes: (i) -x+1, -y+1, -z+2; (ii) -x+3, -y, -z+2.

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 datablocks I, global. DOI: 10.1107/S160053681301369X/im2433sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681301369X/im2433Isup2.hkl

Supporting information file. DOI: 10.1107/S160053681301369X/im2433Isup3.cml

checkCIF report

Comment top

Anthraquinone is a versatile organic redox mediator and is useful for applications such as selective H₂O₂ production through oxygen reduction reaction (Campos-Martin et al., 2006); photo-cleavage of DNA (Henderson et al., 1998); anticancer activity (anthraquinone as central building block) (Barasch et al., 1999) and enzyme/mediator (Dou et al., 2009) etc. Similarly, electrodes that were chemically modified with anthraquinone were useful for several electrochemical (Harish et al., 2009); electrocatalytic (Jürmann et al., 2007; Manisankar et al., 2005); and pH sensor applications (Wong et al., 2004; Lafitte et al., 2008; Wildgoose et al., 2003).

In this work, we aim to prepare new derivatives of anthra [1,2-d]imidazole- 2,6,11–trione for biological activities. In a previous study we have synthesized the 1,3-diallyl-1H-anthra [1,2-d] imidazole-2,6,11(3H)-trione (Afrakssou et al., 2010), and, here we have focused in the reactivity of the exocyclic C=C bond of the allyl substituent towards nitriloxides (Afrakssou et al., 2011). The latter are produced as intermediates in the dehydrohalogenation of (E)-isonicotinaldehyde oxime by a solution of sodium hypochlorite. The oxime then reacts with 1, 3-diallyl-1H-anthra [1, 2 - d] imidazole-2, 6, 11(3H)-trione in a biphasic medium (water-chloroform) at 273 K during 4 h to a unique cycloadduct 1-allyl-3-((3-(pyridin-4-yl)-4,5-dihydroisoxazol-5-yl)methyl)- 1H-anthra[1,2-d]imidazole-2,6,11(3H)-trione (Scheme 1).

The molecule of title compound, C₂₇H₂₀N₄O₄, contains four fused rings, three are six-membered rings and one is the five-membered imidazole ring. The imidazole ring is on one side attached to the allyl chain and on the other side to a (3-(pyridin-4-yl)-4,5-dihydroisoxazol-5-yl)methyl group (Fig.1). The fused ring system is almost planar with the largest deviation from the mean plane being 0.232 (2) A° at C7. In this system, the two pairs of adjacent rings are slightly folded along the common edge (C8–C9) making a dihedral angle of 11.17 (6) °. The isoxazole (N3-O4-C20-C21-C22) ring makes dihedral angles of 27.2 (2) ° and 12.7 (2) ° with the imidazole (N1-N2-C11-C12-C15) and pyridine (N4-C23 to C27) rings, respectively.

Weak intermolecular C19–H19A···O3, C21–H21A···O3, C3–H3···O4 and C3–H3···N3 hydrogen bondings ensures the cohesion of the crystal structure as shown in Fig. 2 and Table 2.

Related literature top

For the use of anthraquinone as an organic redox mediator, see: Campos-Martin et al. (2006); Harish et al. (2009); Jürmann et al. (2007); Manisankar & Gomathi (2005). For the biological activity of anthraquinone derivatives, see: Henderson et al. (1998); Barasch et al. (1999); Dou et al. (2009). For background to pH sensor applications, see: Wong et al. (2004); Lafitte et al. (2008); Wildgoose et al. (2003). For similar compounds, see: Afrakssou et al. (2010, 2011).

Experimental top

To a solution of 1,3-diallyl-1H-anthra[1,2-d]imidazole-2,6,11(3H) -trione (0.5 g, 1.45 mmol) and (E)-isonicotinaldehyde oxime (0.44 g, 3.62 mmol) in chloroform (16 ml) was added dropwise a 24% sodium hypochlorite solution (8 ml) at 273 K. Stirring was continued for 4 h. The organic layer was dried over Na₂SO₄ and the solvent was evaporated under reduced pressure. The residue was then purified by column chromatography on silica gel using a mixture of hexane/ethyl acetate (1/1) as eluent. The yield of the reaction is of 51%. Orange crystals were isolated after the solvent was allowed to evaporate.

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. Hydrogen bonds are shown as dashed lines. Symmetry codes: (i) -x + 1, -y + 1, -z + 2; (ii) -x + 3, -y, -z + 2.

1-(Prop-2-en-1-yl)-3-{[3-(pyridin-4-yl)-4,5-dihydroisoxazol-5-yl]methyl}-1H-anthra[1,2-d]imidazole-2,6,11(3H)-trione top

Crystal data top

C₂₇H₂₀N₄O₄	Z = 2
M_r = 464.47	F(000) = 484
Triclinic, P1	D_x = 1.403 Mg m⁻³
Hall symbol: -P 1	Melting point: 443 K
a = 8.0930 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 12.1191 (3) Å	Cell parameters from 8485 reflections
c = 12.2743 (2) Å	θ = 2.8–26.0°
α = 87.109 (1)°	µ = 0.10 mm⁻¹
β = 73.612 (1)°	T = 296 K
γ = 72.283 (1)°	Block, orange
V = 1099.35 (4) Å³	0.14 × 0.10 × 0.08 mm

Data collection top

Bruker APEXII CCD diffractometer	3900 reflections with I > 2σ(I)
Radiation source: microfocus source	R_int = 0.031
Graphite monochromator	θ_max = 28.7°, θ_min = 1.7°
ϕ and ω scans	h = −10→10
36799 measured reflections	k = −16→16
5659 independent 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)] = 0.048	Hydrogen site location: difference Fourier map
wR(F²) = 0.148	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0711P)² + 0.2464P] where P = (F_o² + 2F_c²)/3
5659 reflections	(Δ/σ)_max < 0.001
316 parameters	Δρ_max = 0.37 e Å⁻³
0 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₂₇H₂₀N₄O₄	γ = 72.283 (1)°
M_r = 464.47	V = 1099.35 (4) Å³
Triclinic, P1	Z = 2
a = 8.0930 (2) Å	Mo Kα radiation
b = 12.1191 (3) Å	µ = 0.10 mm⁻¹
c = 12.2743 (2) Å	T = 296 K
α = 87.109 (1)°	0.14 × 0.10 × 0.08 mm
β = 73.612 (1)°

Data collection top

Bruker APEXII CCD diffractometer	3900 reflections with I > 2σ(I)
36799 measured reflections	R_int = 0.031
5659 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.148	H-atom parameters constrained
S = 1.02	Δρ_max = 0.37 e Å⁻³
5659 reflections	Δρ_min = −0.20 e Å⁻³
316 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	0.5114 (2)	0.62606 (14)	1.11854 (16)	0.0495 (4)
C2	0.3824 (3)	0.73461 (16)	1.1261 (2)	0.0637 (5)
H2	0.3864	0.7808	1.0631	0.076*
C3	0.2504 (3)	0.77342 (18)	1.2256 (2)	0.0742 (7)
H3	0.1658	0.8462	1.2302	0.089*
C4	0.2421 (3)	0.70528 (19)	1.3189 (2)	0.0739 (6)
H4	0.1509	0.7316	1.3860	0.089*
C5	0.3689 (3)	0.59784 (17)	1.31336 (19)	0.0637 (5)
H5	0.3630	0.5521	1.3766	0.076*
C6	0.5051 (2)	0.55819 (14)	1.21343 (15)	0.0488 (4)
C7	0.6385 (2)	0.44158 (14)	1.20925 (14)	0.0463 (4)
C8	0.7922 (2)	0.40617 (13)	1.10555 (13)	0.0383 (3)
C9	0.7841 (2)	0.46768 (13)	1.00512 (13)	0.0417 (3)
C10	0.6459 (2)	0.58148 (15)	1.00850 (16)	0.0498 (4)
C11	0.93761 (19)	0.30551 (12)	1.09642 (12)	0.0362 (3)
C12	1.0529 (2)	0.26122 (13)	0.98806 (12)	0.0376 (3)
C13	1.0379 (2)	0.31860 (15)	0.89005 (13)	0.0464 (4)
H13	1.1144	0.2877	0.8194	0.056*
C14	0.9049 (2)	0.42393 (15)	0.90068 (14)	0.0478 (4)
H14	0.8960	0.4666	0.8363	0.057*
C15	1.1529 (2)	0.14078 (13)	1.11712 (13)	0.0382 (3)
C16	0.9718 (2)	0.24952 (15)	1.29631 (13)	0.0481 (4)
H16A	1.0353	0.1796	1.3274	0.058*
H16B	0.8438	0.2670	1.3348	0.058*
C17	1.0362 (3)	0.34735 (19)	1.31752 (16)	0.0659 (5)
H17	1.1552	0.3440	1.2807	0.079*
C18	0.9359 (5)	0.4370 (2)	1.3844 (2)	0.1064 (10)
H18A	0.8164	0.4428	1.4223	0.128*
H18B	0.9836	0.4953	1.3942	0.128*
C19	1.3115 (2)	0.07767 (14)	0.91585 (13)	0.0418 (4)
H19A	1.4231	0.0492	0.9374	0.050*
H19B	1.3360	0.1169	0.8450	0.050*
C20	1.2483 (2)	−0.02358 (14)	0.89840 (13)	0.0426 (4)
H20	1.2199	−0.0630	0.9698	0.051*
C21	1.3846 (2)	−0.10974 (14)	0.80505 (14)	0.0473 (4)
H21A	1.5044	−0.1010	0.7885	0.057*
H21B	1.3904	−0.1891	0.8245	0.057*
C22	1.3037 (2)	−0.07338 (14)	0.70869 (13)	0.0433 (4)
C23	1.3916 (2)	−0.11054 (15)	0.58912 (14)	0.0464 (4)
C24	1.5579 (3)	−0.19406 (17)	0.55610 (16)	0.0622 (5)
H24	1.6145	−0.2309	0.6101	0.075*
C25	1.6397 (3)	−0.2224 (2)	0.44121 (19)	0.0754 (6)
H25	1.7517	−0.2789	0.4207	0.090*
C26	1.4083 (4)	−0.0959 (2)	0.39166 (17)	0.0716 (6)
H26	1.3550	−0.0618	0.3354	0.086*
C27	1.3145 (3)	−0.06123 (18)	0.50314 (15)	0.0581 (5)
H27	1.2015	−0.0057	0.5206	0.070*
N1	1.00212 (17)	0.22965 (11)	1.17475 (10)	0.0385 (3)
N2	1.17735 (17)	0.15961 (11)	1.00326 (10)	0.0391 (3)
N3	1.14308 (19)	−0.00366 (13)	0.73868 (12)	0.0502 (4)
N4	1.5695 (3)	−0.17468 (18)	0.35938 (15)	0.0773 (6)
O1	0.61239 (19)	0.37492 (12)	1.28523 (12)	0.0702 (4)
O2	0.6424 (2)	0.63732 (13)	0.92318 (13)	0.0750 (4)
O3	1.24659 (15)	0.06244 (10)	1.15952 (9)	0.0478 (3)
O4	1.08962 (15)	0.01876 (11)	0.85700 (10)	0.0524 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0437 (9)	0.0358 (8)	0.0712 (11)	−0.0073 (7)	−0.0243 (8)	0.0000 (8)
C2	0.0596 (12)	0.0400 (10)	0.0947 (15)	−0.0030 (8)	−0.0391 (11)	0.0001 (10)
C3	0.0565 (12)	0.0461 (11)	0.1142 (19)	0.0086 (9)	−0.0374 (12)	−0.0199 (12)
C4	0.0505 (11)	0.0595 (13)	0.0962 (17)	0.0019 (9)	−0.0117 (11)	−0.0244 (12)
C5	0.0499 (10)	0.0529 (11)	0.0731 (13)	−0.0035 (8)	−0.0046 (9)	−0.0098 (9)
C6	0.0404 (8)	0.0387 (9)	0.0618 (10)	−0.0068 (7)	−0.0107 (7)	−0.0039 (7)
C7	0.0421 (8)	0.0378 (8)	0.0510 (9)	−0.0075 (7)	−0.0056 (7)	0.0013 (7)
C8	0.0387 (8)	0.0332 (7)	0.0417 (8)	−0.0095 (6)	−0.0105 (6)	0.0011 (6)
C9	0.0428 (8)	0.0371 (8)	0.0479 (9)	−0.0112 (6)	−0.0186 (7)	0.0064 (6)
C10	0.0497 (9)	0.0415 (9)	0.0625 (11)	−0.0120 (7)	−0.0259 (8)	0.0115 (8)
C11	0.0379 (7)	0.0337 (7)	0.0350 (7)	−0.0096 (6)	−0.0086 (6)	0.0019 (6)
C12	0.0368 (7)	0.0378 (8)	0.0374 (7)	−0.0095 (6)	−0.0107 (6)	−0.0015 (6)
C13	0.0504 (9)	0.0511 (10)	0.0351 (8)	−0.0126 (8)	−0.0109 (7)	0.0002 (7)
C14	0.0559 (10)	0.0498 (10)	0.0400 (8)	−0.0161 (8)	−0.0184 (7)	0.0104 (7)
C15	0.0361 (7)	0.0371 (8)	0.0392 (8)	−0.0081 (6)	−0.0102 (6)	−0.0004 (6)
C16	0.0589 (10)	0.0446 (9)	0.0329 (8)	−0.0097 (8)	−0.0073 (7)	0.0039 (6)
C17	0.0908 (15)	0.0682 (13)	0.0444 (10)	−0.0304 (12)	−0.0208 (10)	0.0021 (9)
C18	0.173 (3)	0.0811 (18)	0.0647 (15)	−0.0454 (19)	−0.0226 (17)	−0.0155 (13)
C19	0.0333 (7)	0.0453 (9)	0.0395 (8)	−0.0044 (6)	−0.0055 (6)	−0.0059 (6)
C20	0.0400 (8)	0.0430 (8)	0.0386 (8)	−0.0065 (6)	−0.0079 (6)	−0.0011 (6)
C21	0.0465 (9)	0.0412 (9)	0.0468 (9)	−0.0034 (7)	−0.0109 (7)	−0.0057 (7)
C22	0.0423 (8)	0.0434 (9)	0.0439 (8)	−0.0153 (7)	−0.0083 (7)	−0.0019 (7)
C23	0.0532 (9)	0.0459 (9)	0.0426 (8)	−0.0237 (8)	−0.0075 (7)	−0.0013 (7)
C24	0.0672 (12)	0.0572 (11)	0.0503 (10)	−0.0154 (9)	−0.0008 (9)	−0.0049 (8)
C25	0.0807 (15)	0.0671 (14)	0.0613 (13)	−0.0206 (12)	0.0070 (11)	−0.0112 (11)
C26	0.1029 (18)	0.0818 (15)	0.0465 (10)	−0.0523 (15)	−0.0207 (11)	0.0064 (10)
C27	0.0685 (12)	0.0629 (12)	0.0505 (10)	−0.0312 (10)	−0.0166 (9)	0.0033 (9)
N1	0.0419 (7)	0.0348 (6)	0.0330 (6)	−0.0055 (5)	−0.0083 (5)	0.0013 (5)
N2	0.0373 (6)	0.0388 (7)	0.0349 (6)	−0.0040 (5)	−0.0078 (5)	−0.0020 (5)
N3	0.0441 (8)	0.0569 (9)	0.0486 (8)	−0.0131 (7)	−0.0127 (6)	−0.0051 (7)
N4	0.1033 (16)	0.0782 (13)	0.0495 (10)	−0.0441 (12)	−0.0005 (10)	−0.0073 (9)
O1	0.0647 (8)	0.0511 (8)	0.0652 (8)	−0.0048 (6)	0.0122 (6)	0.0122 (6)
O2	0.0784 (10)	0.0606 (9)	0.0739 (9)	−0.0016 (7)	−0.0277 (8)	0.0263 (7)
O3	0.0435 (6)	0.0452 (6)	0.0494 (6)	−0.0029 (5)	−0.0168 (5)	0.0054 (5)
O4	0.0367 (6)	0.0643 (8)	0.0502 (7)	−0.0081 (5)	−0.0083 (5)	−0.0125 (6)

Geometric parameters (Å, º) top

C1—C6	1.390 (3)	C16—C17	1.493 (3)
C1—C2	1.397 (2)	C16—H16A	0.9700
C1—C10	1.479 (3)	C16—H16B	0.9700
C2—C3	1.368 (3)	C17—C18	1.300 (3)
C2—H2	0.9300	C17—H17	0.9300
C3—C4	1.376 (3)	C18—H18A	0.9300
C3—H3	0.9300	C18—H18B	0.9300
C4—C5	1.382 (3)	C19—N2	1.4525 (18)
C4—H4	0.9300	C19—C20	1.511 (2)
C5—C6	1.387 (2)	C19—H19A	0.9700
C5—H5	0.9300	C19—H19B	0.9700
C6—C7	1.487 (2)	C20—O4	1.453 (2)
C7—O1	1.218 (2)	C20—C21	1.525 (2)
C7—C8	1.479 (2)	C20—H20	0.9800
C8—C11	1.397 (2)	C21—C22	1.494 (2)
C8—C9	1.415 (2)	C21—H21A	0.9700
C9—C14	1.388 (2)	C21—H21B	0.9700
C9—C10	1.482 (2)	C22—N3	1.278 (2)
C10—O2	1.220 (2)	C22—C23	1.465 (2)
C11—N1	1.3943 (19)	C23—C24	1.380 (3)
C11—C12	1.412 (2)	C23—C27	1.393 (3)
C12—C13	1.376 (2)	C24—C25	1.389 (3)
C12—N2	1.3760 (19)	C24—H24	0.9300
C13—C14	1.381 (2)	C25—N4	1.315 (3)
C13—H13	0.9300	C25—H25	0.9300
C14—H14	0.9300	C26—N4	1.326 (3)
C15—O3	1.2171 (18)	C26—C27	1.380 (3)
C15—N2	1.3726 (19)	C26—H26	0.9300
C15—N1	1.3927 (19)	C27—H27	0.9300
C16—N1	1.4621 (19)	N3—O4	1.4084 (18)

C6—C1—C2	119.35 (18)	C18—C17—C16	123.9 (2)
C6—C1—C10	120.62 (15)	C18—C17—H17	118.1
C2—C1—C10	119.92 (17)	C16—C17—H17	118.1
C3—C2—C1	120.4 (2)	C17—C18—H18A	120.0
C3—C2—H2	119.8	C17—C18—H18B	120.0
C1—C2—H2	119.8	H18A—C18—H18B	120.0
C2—C3—C4	120.29 (19)	N2—C19—C20	111.63 (12)
C2—C3—H3	119.9	N2—C19—H19A	109.3
C4—C3—H3	119.9	C20—C19—H19A	109.3
C3—C4—C5	120.2 (2)	N2—C19—H19B	109.3
C3—C4—H4	119.9	C20—C19—H19B	109.3
C5—C4—H4	119.9	H19A—C19—H19B	108.0
C4—C5—C6	120.1 (2)	O4—C20—C19	108.93 (13)
C4—C5—H5	120.0	O4—C20—C21	104.00 (12)
C6—C5—H5	120.0	C19—C20—C21	112.82 (13)
C5—C6—C1	119.71 (17)	O4—C20—H20	110.3
C5—C6—C7	118.96 (17)	C19—C20—H20	110.3
C1—C6—C7	121.30 (15)	C21—C20—H20	110.3
O1—C7—C8	121.68 (15)	C22—C21—C20	100.34 (13)
O1—C7—C6	120.30 (15)	C22—C21—H21A	111.7
C8—C7—C6	117.76 (14)	C20—C21—H21A	111.7
C11—C8—C9	116.86 (13)	C22—C21—H21B	111.7
C11—C8—C7	123.26 (14)	C20—C21—H21B	111.7
C9—C8—C7	119.39 (14)	H21A—C21—H21B	109.5
C14—C9—C8	121.33 (15)	N3—C22—C23	120.26 (16)
C14—C9—C10	117.88 (15)	N3—C22—C21	113.77 (14)
C8—C9—C10	120.79 (15)	C23—C22—C21	125.98 (15)
O2—C10—C1	120.60 (16)	C24—C23—C27	116.82 (17)
O2—C10—C9	121.25 (17)	C24—C23—C22	121.28 (17)
C1—C10—C9	118.15 (15)	C27—C23—C22	121.87 (17)
N1—C11—C8	134.04 (13)	C23—C24—C25	119.1 (2)
N1—C11—C12	106.27 (12)	C23—C24—H24	120.4
C8—C11—C12	119.68 (13)	C25—C24—H24	120.4
C13—C12—N2	129.78 (14)	N4—C25—C24	124.4 (2)
C13—C12—C11	122.57 (14)	N4—C25—H25	117.8
N2—C12—C11	107.59 (13)	C24—C25—H25	117.8
C12—C13—C14	117.41 (14)	N4—C26—C27	124.4 (2)
C12—C13—H13	121.3	N4—C26—H26	117.8
C14—C13—H13	121.3	C27—C26—H26	117.8
C13—C14—C9	121.59 (15)	C26—C27—C23	119.0 (2)
C13—C14—H14	119.2	C26—C27—H27	120.5
C9—C14—H14	119.2	C23—C27—H27	120.5
O3—C15—N2	126.58 (14)	C15—N1—C11	109.31 (12)
O3—C15—N1	126.66 (14)	C15—N1—C16	118.49 (13)
N2—C15—N1	106.75 (13)	C11—N1—C16	129.16 (13)
N1—C16—C17	111.20 (13)	C15—N2—C12	109.96 (12)
N1—C16—H16A	109.4	C15—N2—C19	122.55 (13)
C17—C16—H16A	109.4	C12—N2—C19	127.42 (13)
N1—C16—H16B	109.4	C22—N3—O4	109.39 (13)
C17—C16—H16B	109.4	C25—N4—C26	116.19 (19)
H16A—C16—H16B	108.0	N3—O4—C20	108.52 (11)

C6—C1—C2—C3	−0.5 (3)	N1—C16—C17—C18	125.5 (2)
C10—C1—C2—C3	175.79 (17)	N2—C19—C20—O4	63.70 (16)
C1—C2—C3—C4	−0.7 (3)	N2—C19—C20—C21	178.64 (13)
C2—C3—C4—C5	1.0 (3)	O4—C20—C21—C22	18.17 (16)
C3—C4—C5—C6	−0.1 (3)	C19—C20—C21—C22	−99.71 (15)
C4—C5—C6—C1	−1.1 (3)	C20—C21—C22—N3	−12.02 (19)
C4—C5—C6—C7	−179.20 (18)	C20—C21—C22—C23	168.07 (15)
C2—C1—C6—C5	1.4 (3)	N3—C22—C23—C24	−173.79 (16)
C10—C1—C6—C5	−174.83 (17)	C21—C22—C23—C24	6.1 (3)
C2—C1—C6—C7	179.42 (16)	N3—C22—C23—C27	8.2 (3)
C10—C1—C6—C7	3.2 (3)	C21—C22—C23—C27	−171.93 (16)
C5—C6—C7—O1	11.5 (3)	C27—C23—C24—C25	1.2 (3)
C1—C6—C7—O1	−166.50 (18)	C22—C23—C24—C25	−176.92 (17)
C5—C6—C7—C8	−174.24 (16)	C23—C24—C25—N4	0.0 (3)
C1—C6—C7—C8	7.7 (2)	N4—C26—C27—C23	0.3 (3)
O1—C7—C8—C11	−13.9 (3)	C24—C23—C27—C26	−1.4 (3)
C6—C7—C8—C11	171.97 (15)	C22—C23—C27—C26	176.75 (16)
O1—C7—C8—C9	157.86 (17)	O3—C15—N1—C11	176.95 (15)
C6—C7—C8—C9	−16.3 (2)	N2—C15—N1—C11	−2.11 (16)
C11—C8—C9—C14	6.1 (2)	O3—C15—N1—C16	14.9 (2)
C7—C8—C9—C14	−166.19 (15)	N2—C15—N1—C16	−164.21 (13)
C11—C8—C9—C10	−173.72 (14)	C8—C11—N1—C15	178.90 (16)
C7—C8—C9—C10	14.0 (2)	C12—C11—N1—C15	−0.01 (16)
C6—C1—C10—O2	174.24 (18)	C8—C11—N1—C16	−21.5 (3)
C2—C1—C10—O2	−2.0 (3)	C12—C11—N1—C16	159.59 (15)
C6—C1—C10—C9	−5.8 (2)	C17—C16—N1—C15	99.02 (18)
C2—C1—C10—C9	178.01 (15)	C17—C16—N1—C11	−59.0 (2)
C14—C9—C10—O2	−2.8 (3)	O3—C15—N2—C12	−175.56 (15)
C8—C9—C10—O2	176.99 (16)	N1—C15—N2—C12	3.51 (17)
C14—C9—C10—C1	177.19 (15)	O3—C15—N2—C19	7.3 (2)
C8—C9—C10—C1	−3.0 (2)	N1—C15—N2—C19	−173.60 (13)
C9—C8—C11—N1	172.45 (16)	C13—C12—N2—C15	173.53 (16)
C7—C8—C11—N1	−15.6 (3)	C11—C12—N2—C15	−3.55 (17)
C9—C8—C11—C12	−8.8 (2)	C13—C12—N2—C19	−9.5 (3)
C7—C8—C11—C12	163.18 (14)	C11—C12—N2—C19	173.38 (13)
N1—C11—C12—C13	−175.20 (14)	C20—C19—N2—C15	78.33 (18)
C8—C11—C12—C13	5.7 (2)	C20—C19—N2—C12	−98.24 (18)
N1—C11—C12—N2	2.14 (16)	C23—C22—N3—O4	−179.88 (13)
C8—C11—C12—N2	−176.96 (13)	C21—C22—N3—O4	0.2 (2)
N2—C12—C13—C14	−176.07 (16)	C24—C25—N4—C26	−1.1 (3)
C11—C12—C13—C14	0.6 (2)	C27—C26—N4—C25	1.0 (3)
C12—C13—C14—C9	−3.5 (3)	C22—N3—O4—C20	12.78 (18)
C8—C9—C14—C13	0.1 (3)	C19—C20—O4—N3	100.89 (14)
C10—C9—C14—C13	179.91 (15)	C21—C20—O4—N3	−19.64 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···N3ⁱ	0.93	2.58	3.471 (2)	160
C3—H3···O4ⁱ	0.93	2.67	3.470 (2)	145
C19—H19A···O3ⁱⁱ	0.97	2.56	3.3356 (19)	137
C21—H21A···O3ⁱⁱ	0.97	2.45	3.350 (2)	154

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

Experimental details

Crystal data
Chemical formula	C₂₇H₂₀N₄O₄
M_r	464.47
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	8.0930 (2), 12.1191 (3), 12.2743 (2)
α, β, γ (°)	87.109 (1), 73.612 (1), 72.283 (1)
V (Å³)	1099.35 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.14 × 0.10 × 0.08

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	36799, 5659, 3900
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.676

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.148, 1.02
No. of reflections	5659
No. of parameters	316
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.37, −0.20

Computer programs: APEX2 (Bruker, 2009), SAINT-Plus (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012), PLATON (Spek, 2009) and publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···N3ⁱ	0.93	2.58	3.471 (2)	160.0
C3—H3···O4ⁱ	0.93	2.67	3.470 (2)	145.1
C19—H19A···O3ⁱⁱ	0.97	2.56	3.3356 (19)	136.9
C21—H21A···O3ⁱⁱ	0.97	2.45	3.350 (2)	153.7

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

References

Afrakssou, Z., Haoudi, A., Capet, F., Rolando, C. & El Ammari, L. (2011). Acta Cryst. E67, o1363–o1364. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Afrakssou, Z., Rodi, Y. K., Zouihri, H., Essassi, E. M. & Ng, S. W. (2010). Acta Cryst. E66, o1851. Web of Science CSD CrossRef IUCr Journals Google Scholar
Barasch, D., Zipori, O., Ringel, I., Ginsbury, I., Samuni, A. & Katzhendler, J. (1999). Eur. J. Med. Chem. 34, 597–615. Web of Science PubMed CAS Google Scholar
Bruker (2009). APEX2 and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Campos-Martin, J. M., Blanco-Brieva, G. & Fierro, J. L. G. (2006). Angew. Chem. Int. Ed. 45, 6962–6984. CAS Google Scholar
Dou, Y., Haswell, S., Greenman, J. & Wadhawan, J. (2009). Electrochem. Commun. 11, 1976–1981. Web of Science CrossRef CAS Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Harish, S., Sridharan, D., Kumar, S. S., Joseph, J. & Phani, K. L. N. (2009). Electrochim. Acta, 54, 3618–3622. Web of Science CrossRef CAS Google Scholar
Henderson, P. T., Armitage, B. & Schuster, G. B. (1998). Biochemistry, 37, 2991–3000. Web of Science CrossRef CAS PubMed Google Scholar
Jürmann, G., Schiffrin, D. J. & Tammeveski, K. (2007). Electrochim. Acta, 53, 390–399. Google Scholar
Lafitte, V. G. H., Wang, W., Yashina, A. S. & Lawrence, N. S. (2008). Electrochem. Commun. 10, 1831–1834. Web of Science CrossRef CAS Google Scholar
Manisankar, P. & Gomathi, A. (2005). J. Mol. Catal. A Chem. 232, 45–52. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals 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
Wildgoose, G. G., Pandurangappa, M., Lawrence, N. S., Jiang, L., Jones, T. G. J. & Compton, R. G. (2003). Talanta, 60, 887–893. Web of Science CrossRef PubMed CAS Google Scholar
Wong, E. L. S., Erohkin, P. & Gooding, J. J. (2004). Electrochem. Commun. 6, 648–654. Web of Science CrossRef CAS Google Scholar

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Volume 69| Part 6| June 2013| Pages o945-o946

doi:10.1107/S160053681301369X

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

1-(Prop-2-en-1-yl)-3-{[3-(pyridin-4-yl)-4,5-di­hydro­isoxazol-5-yl]meth­yl}-1H-anthra[1,2-d]imidazole-2,6,11(3H)-trione

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Experimental

Crystal data

Data collection

Refinement

Supporting information

References

organic compounds

1-(Prop-2-en-1-yl)-3-{[3-(pyridin-4-yl)-4,5-dihydroisoxazol-5-yl]methyl}-1H-anthra[1,2-d]imidazole-2,6,11(3H)-trione