3-Allyl-1-{[3-(4-nitro-phen-yl)-4,5-dihydro-1,3-oxazol-5-yl]meth-yl}-1H-anthra[1,2-d]imidazole-2,6,11(3H)-trione.

The mol-ecular structure of the title compound, C(28)H(20)N(4)O(6), consists of three fused six-membered rings (A,B,C) and one five-membered ring (D). The latter is linked to an isoxazole ring (E) via a methyl-ene unit. A 4-nitro-phenyl substituent (F) is attached to the isoxazole. The fused five and six-membered rings (C,D) are almost coplanar with an r.m.s. deviation of 0.0345 Å and make a dihedral angle of 9.40 (8)° with ring A. The isoxazole and 4-nitro-phenyl rings (E,F) are also almost coplanar with the imidazole and the fused adjacent ring (C,D), forming a dihedral angle of 11.4 (6)°. The crystal packing displays inter-molecular C-H⋯O hydrogen bonding. An intra-molecular C-H⋯O inter-action also occurs.

Related literature

For the biological activity of anthraquinone derivatives, see: Agarwal et al. (2000 ▶); Barnard et al. (1995 ▶); Chen et al. (2007 ▶); Haug et al. (2003 ▶); Iizuka et al. (2004 ▶); Koyamaa et al. (2002 ▶); Su et al. (2005 ▶); Wu et al. (2005 ▶); Yen et al. (2000 ▶). For a derivative of the title compound, see: Afrakssou et al. (2010 ▶). For the use of related compounds as synthetic dyes, see: Simi et al. (1995 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C28H20N4O6

M = 508.48

Monoclinic,

a = 10.0780 (3) Å

b = 22.7094 (6) Å

c = 11.2729 (3) Å

β = 113.809 (1)°

V = 2360.41 (11) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 296 K

0.40 × 0.14 × 0.11 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS, Bruker, 2009) ▶ T min = 0.704, T max = 0.745

47772 measured reflections

4828 independent reflections

2998 reflections with I > 2σ(I)

R int = 0.048

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.111

S = 1.00

4828 reflections

343 parameters

H-atom parameters constrained

Δρmax = 0.12 e Å−3

Δρmin = −0.15 e Å−3

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, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811016606/im2283sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811016606/im2283Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811016606/im2283Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C28H20N4O6	F(000) = 1056
Mr = 508.48	Dx = 1.431 Mg m−3
Monoclinic, P21/n	Melting point: 471 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 10.0780 (3) Å	Cell parameters from 7395 reflections
b = 22.7094 (6) Å	θ = 2.4–21.5°
c = 11.2729 (3) Å	µ = 0.10 mm−1
β = 113.809 (1)°	T = 296 K
V = 2360.41 (11) Å3	Prism, yellow
Z = 4	0.40 × 0.14 × 0.11 mm

Bruker APEXII CCD diffractometer	4828 independent reflections
Radiation source: fine-focus sealed tube	2998 reflections with I > 2σ(I)
graphite	Rint = 0.048
φ and ω scans	θmax = 26.4°, θmin = 2.5°
Absorption correction: multi-scan (SADABS, Bruker, 2009)	h = −12→12
Tmin = 0.704, Tmax = 0.745	k = −28→28
47772 measured reflections	l = −12→14

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.111	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0455P)2 + 0.4447P] where P = (Fo2 + 2Fc2)/3
4828 reflections	(Δ/σ)max = 0.001
343 parameters	Δρmax = 0.12 e Å−3
0 restraints	Δρmin = −0.15 e Å−3

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 > 2σ(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.

	x	y	z	Uiso*/Ueq
C1	0.6321 (2)	0.82375 (9)	0.19097 (19)	0.0612 (5)
C2	0.85135 (19)	0.84194 (8)	0.35084 (17)	0.0552 (4)
C3	0.81023 (17)	0.89317 (8)	0.27367 (15)	0.0502 (4)
C4	0.90411 (17)	0.94182 (7)	0.30538 (15)	0.0475 (4)
C5	1.04177 (18)	0.93398 (7)	0.40936 (15)	0.0505 (4)
C6	1.0776 (2)	0.88249 (8)	0.48157 (16)	0.0593 (5)
H6	1.1683	0.8794	0.5498	0.071*
C7	0.9829 (2)	0.83582 (8)	0.45530 (17)	0.0622 (5)
H7	1.0064	0.8018	0.5055	0.075*
C8	1.1555 (2)	0.97997 (8)	0.44241 (17)	0.0574 (4)
C9	1.1231 (2)	1.03401 (8)	0.36364 (17)	0.0556 (4)
C10	0.98508 (19)	1.04342 (7)	0.26723 (16)	0.0527 (4)
C11	0.86591 (19)	1.00068 (8)	0.24546 (16)	0.0524 (4)
C12	1.2303 (2)	1.07627 (9)	0.3858 (2)	0.0712 (5)
H12	1.3224	1.0703	0.4505	0.085*
C13	1.2012 (3)	1.12668 (10)	0.3127 (2)	0.0793 (6)
H13	1.2730	1.1550	0.3292	0.095*
C14	1.0663 (3)	1.13554 (9)	0.2151 (2)	0.0754 (6)
H14	1.0482	1.1692	0.1641	0.090*
C15	0.9574 (2)	1.09440 (8)	0.19255 (19)	0.0651 (5)
H15	0.8658	1.1008	0.1275	0.078*
C16	0.59135 (18)	0.91052 (8)	0.05248 (16)	0.0576 (5)
H16A	0.5982	0.9527	0.0669	0.069*
H16B	0.4900	0.8995	0.0226	0.069*
C17	0.64489 (18)	0.89559 (9)	−0.05152 (17)	0.0588 (5)
H17	0.6223	0.8546	−0.0797	0.071*
C18	0.58172 (18)	0.93738 (8)	−0.16582 (17)	0.0617 (5)
H18A	0.5628	0.9177	−0.2474	0.074*
H18B	0.4935	0.9560	−0.1695	0.074*
C19	0.70447 (18)	0.98060 (8)	−0.13153 (16)	0.0553 (4)
C20	0.69973 (18)	1.03873 (8)	−0.18912 (16)	0.0546 (4)
C21	0.5711 (2)	1.06028 (9)	−0.28290 (18)	0.0640 (5)
H21	0.4882	1.0370	−0.3120	0.077*
C22	0.5655 (2)	1.11605 (9)	−0.33315 (19)	0.0701 (5)
H22	0.4792	1.1305	−0.3955	0.084*
C23	0.6886 (2)	1.15008 (8)	−0.2904 (2)	0.0662 (5)
C24	0.8184 (2)	1.12962 (10)	−0.1991 (2)	0.0727 (6)
H24	0.9011	1.1530	−0.1718	0.087*
C25	0.8234 (2)	1.07410 (9)	−0.14903 (19)	0.0655 (5)
H25	0.9106	1.0599	−0.0875	0.079*
C26	0.7429 (2)	0.74050 (9)	0.3414 (2)	0.0749 (6)
H26A	0.6442	0.7270	0.3176	0.090*
H26B	0.7923	0.7385	0.4351	0.090*
C27	0.8169 (2)	0.70030 (9)	0.2829 (2)	0.0776 (6)
H27	0.8222	0.6608	0.3062	0.093*
C28	0.8743 (3)	0.71473 (12)	0.2031 (3)	0.0922 (7)
H28A	0.8718	0.7537	0.1768	0.111*
H28B	0.9182	0.6862	0.1720	0.111*
N1	0.67395 (14)	0.88059 (7)	0.17487 (13)	0.0554 (4)
N2	0.73969 (16)	0.80148 (7)	0.30080 (15)	0.0633 (4)
N3	0.82302 (15)	0.96221 (7)	−0.04143 (14)	0.0606 (4)
N4	0.6801 (3)	1.20974 (9)	−0.3438 (2)	0.0907 (6)
O1	0.52115 (15)	0.79872 (6)	0.12021 (14)	0.0768 (4)
O2	0.73990 (14)	1.01619 (6)	0.18463 (13)	0.0677 (4)
O3	1.27476 (15)	0.97262 (6)	0.53085 (13)	0.0835 (4)
O4	0.80057 (12)	0.90603 (6)	0.00001 (12)	0.0663 (4)
O5	0.5638 (2)	1.22624 (8)	−0.4262 (2)	0.1111 (6)
O6	0.7864 (2)	1.24061 (9)	−0.3026 (3)	0.1445 (9)

	U11	U22	U33	U12	U13	U23
C1	0.0496 (11)	0.0657 (13)	0.0690 (12)	−0.0039 (10)	0.0245 (10)	−0.0025 (10)
C2	0.0513 (11)	0.0581 (11)	0.0572 (10)	−0.0025 (9)	0.0231 (9)	−0.0016 (8)
C3	0.0439 (10)	0.0582 (11)	0.0491 (9)	0.0041 (8)	0.0193 (8)	−0.0003 (8)
C4	0.0464 (10)	0.0516 (10)	0.0463 (9)	0.0034 (8)	0.0204 (8)	−0.0033 (7)
C5	0.0488 (10)	0.0559 (10)	0.0464 (9)	0.0008 (8)	0.0188 (8)	−0.0058 (8)
C6	0.0528 (11)	0.0668 (12)	0.0495 (9)	0.0057 (9)	0.0115 (8)	0.0018 (9)
C7	0.0623 (12)	0.0614 (12)	0.0578 (11)	0.0031 (10)	0.0190 (9)	0.0077 (9)
C8	0.0540 (11)	0.0654 (12)	0.0470 (9)	−0.0015 (9)	0.0145 (9)	−0.0099 (8)
C9	0.0584 (11)	0.0547 (11)	0.0557 (10)	−0.0037 (9)	0.0251 (9)	−0.0144 (8)
C10	0.0584 (11)	0.0489 (10)	0.0569 (10)	0.0057 (8)	0.0294 (9)	−0.0085 (8)
C11	0.0495 (11)	0.0581 (11)	0.0513 (9)	0.0077 (9)	0.0219 (8)	−0.0055 (8)
C12	0.0700 (13)	0.0670 (13)	0.0737 (13)	−0.0131 (11)	0.0258 (11)	−0.0153 (10)
C13	0.0819 (16)	0.0621 (14)	0.1010 (17)	−0.0139 (12)	0.0444 (14)	−0.0140 (12)
C14	0.0913 (17)	0.0502 (11)	0.0998 (16)	0.0048 (11)	0.0543 (14)	0.0004 (11)
C15	0.0718 (13)	0.0559 (11)	0.0748 (12)	0.0107 (10)	0.0371 (11)	−0.0013 (9)
C16	0.0391 (9)	0.0674 (11)	0.0611 (11)	0.0029 (8)	0.0147 (8)	0.0008 (9)
C17	0.0413 (10)	0.0693 (12)	0.0606 (10)	0.0026 (9)	0.0151 (8)	−0.0027 (9)
C18	0.0412 (10)	0.0799 (13)	0.0575 (10)	0.0015 (9)	0.0131 (8)	−0.0025 (9)
C19	0.0377 (10)	0.0742 (12)	0.0508 (9)	0.0038 (9)	0.0147 (8)	−0.0049 (9)
C20	0.0420 (10)	0.0692 (12)	0.0507 (9)	0.0026 (8)	0.0168 (8)	−0.0098 (8)
C21	0.0500 (11)	0.0681 (13)	0.0609 (11)	−0.0024 (9)	0.0090 (9)	−0.0084 (9)
C22	0.0600 (13)	0.0716 (13)	0.0649 (12)	0.0062 (11)	0.0109 (10)	−0.0085 (10)
C23	0.0684 (14)	0.0582 (12)	0.0739 (12)	0.0016 (10)	0.0309 (11)	−0.0113 (10)
C24	0.0553 (13)	0.0743 (14)	0.0889 (14)	−0.0077 (11)	0.0293 (11)	−0.0138 (12)
C25	0.0417 (10)	0.0818 (14)	0.0683 (12)	−0.0003 (10)	0.0174 (9)	−0.0063 (10)
C26	0.0668 (13)	0.0692 (13)	0.0855 (14)	−0.0114 (11)	0.0273 (11)	0.0125 (11)
C27	0.0647 (14)	0.0634 (13)	0.0915 (16)	−0.0019 (11)	0.0179 (12)	0.0047 (11)
C28	0.0823 (16)	0.0928 (17)	0.1015 (18)	−0.0009 (14)	0.0369 (15)	−0.0112 (14)
N1	0.0402 (8)	0.0646 (10)	0.0581 (8)	−0.0012 (7)	0.0164 (7)	0.0008 (7)
N2	0.0554 (10)	0.0604 (10)	0.0703 (10)	−0.0051 (8)	0.0216 (8)	0.0070 (8)
N3	0.0408 (8)	0.0796 (11)	0.0598 (9)	0.0054 (8)	0.0188 (7)	0.0010 (8)
N4	0.0901 (16)	0.0661 (13)	0.1166 (17)	0.0044 (12)	0.0426 (14)	−0.0096 (12)
O1	0.0551 (8)	0.0801 (10)	0.0868 (9)	−0.0157 (7)	0.0197 (7)	−0.0064 (7)
O2	0.0528 (8)	0.0662 (8)	0.0803 (9)	0.0133 (6)	0.0230 (7)	0.0037 (6)
O3	0.0639 (9)	0.0907 (11)	0.0692 (8)	−0.0144 (8)	−0.0008 (7)	0.0015 (7)
O4	0.0420 (7)	0.0861 (10)	0.0672 (8)	0.0113 (6)	0.0182 (6)	0.0102 (7)
O5	0.1209 (16)	0.0787 (12)	0.1199 (14)	0.0141 (11)	0.0344 (13)	0.0101 (10)
O6	0.1056 (16)	0.0775 (12)	0.233 (3)	−0.0174 (11)	0.0507 (16)	0.0068 (14)

C1—O1	1.221 (2)	C16—H16B	0.9700
C1—N2	1.371 (2)	C17—O4	1.456 (2)
C1—N1	1.392 (2)	C17—C18	1.518 (2)
C2—C7	1.379 (2)	C17—H17	0.9800
C2—N2	1.384 (2)	C18—C19	1.502 (2)
C2—C3	1.411 (2)	C18—H18A	0.9700
C3—C4	1.404 (2)	C18—H18B	0.9700
C3—N1	1.405 (2)	C19—N3	1.286 (2)
C4—C5	1.420 (2)	C19—C20	1.463 (3)
C4—C11	1.477 (2)	C20—C21	1.390 (2)
C5—C6	1.387 (2)	C20—C25	1.396 (2)
C5—C8	1.483 (2)	C21—C22	1.379 (3)
C6—C7	1.376 (2)	C21—H21	0.9300
C6—H6	0.9300	C22—C23	1.373 (3)
C7—H7	0.9300	C22—H22	0.9300
C8—O3	1.224 (2)	C23—C24	1.378 (3)
C8—C9	1.472 (3)	C23—N4	1.471 (3)
C9—C12	1.390 (3)	C24—C25	1.374 (3)
C9—C10	1.393 (2)	C24—H24	0.9300
C10—C15	1.392 (2)	C25—H25	0.9300
C10—C11	1.486 (2)	C26—N2	1.455 (2)
C11—O2	1.2264 (19)	C26—C27	1.490 (3)
C12—C13	1.371 (3)	C26—H26A	0.9700
C12—H12	0.9300	C26—H26B	0.9700
C13—C14	1.375 (3)	C27—C28	1.294 (3)
C13—H13	0.9300	C27—H27	0.9300
C14—C15	1.384 (3)	C28—H28A	0.9300
C14—H14	0.9300	C28—H28B	0.9300
C15—H15	0.9300	N3—O4	1.408 (2)
C16—N1	1.460 (2)	N4—O6	1.206 (3)
C16—C17	1.514 (2)	N4—O5	1.224 (2)
C16—H16A	0.9700
O1—C1—N2	126.88 (18)	O4—C17—H17	110.8
O1—C1—N1	126.32 (18)	C16—C17—H17	110.8
N2—C1—N1	106.80 (16)	C18—C17—H17	110.8
C7—C2—N2	128.61 (17)	C19—C18—C17	99.82 (14)
C7—C2—C3	123.44 (17)	C19—C18—H18A	111.8
N2—C2—C3	107.93 (15)	C17—C18—H18A	111.8
C4—C3—N1	134.81 (15)	C19—C18—H18B	111.8
C4—C3—C2	119.47 (15)	C17—C18—H18B	111.8
N1—C3—C2	105.71 (15)	H18A—C18—H18B	109.5
C3—C4—C5	116.42 (15)	N3—C19—C20	119.80 (16)
C3—C4—C11	124.85 (15)	N3—C19—C18	113.39 (16)
C5—C4—C11	118.57 (15)	C20—C19—C18	126.82 (15)
C6—C5—C4	121.74 (16)	C21—C20—C25	118.73 (18)
C6—C5—C8	117.06 (16)	C21—C20—C19	120.55 (17)
C4—C5—C8	121.17 (15)	C25—C20—C19	120.70 (16)
C7—C6—C5	121.98 (16)	C22—C21—C20	120.41 (18)
C7—C6—H6	119.0	C22—C21—H21	119.8
C5—C6—H6	119.0	C20—C21—H21	119.8
C6—C7—C2	116.76 (17)	C23—C22—C21	119.46 (19)
C6—C7—H7	121.6	C23—C22—H22	120.3
C2—C7—H7	121.6	C21—C22—H22	120.3
O3—C8—C9	120.70 (17)	C22—C23—C24	121.52 (19)
O3—C8—C5	120.92 (17)	C22—C23—N4	118.7 (2)
C9—C8—C5	118.36 (16)	C24—C23—N4	119.8 (2)
C12—C9—C10	119.54 (18)	C25—C24—C23	118.87 (19)
C12—C9—C8	120.01 (17)	C25—C24—H24	120.6
C10—C9—C8	120.45 (16)	C23—C24—H24	120.6
C15—C10—C9	119.50 (17)	C24—C25—C20	120.99 (18)
C15—C10—C11	119.50 (17)	C24—C25—H25	119.5
C9—C10—C11	120.97 (16)	C20—C25—H25	119.5
O2—C11—C4	122.39 (16)	N2—C26—C27	113.34 (18)
O2—C11—C10	119.36 (16)	N2—C26—H26A	108.9
C4—C11—C10	118.15 (15)	C27—C26—H26A	108.9
C13—C12—C9	120.4 (2)	N2—C26—H26B	108.9
C13—C12—H12	119.8	C27—C26—H26B	108.9
C9—C12—H12	119.8	H26A—C26—H26B	107.7
C12—C13—C14	120.4 (2)	C28—C27—C26	126.6 (2)
C12—C13—H13	119.8	C28—C27—H27	116.7
C14—C13—H13	119.8	C26—C27—H27	116.7
C13—C14—C15	120.2 (2)	C27—C28—H28A	120.0
C13—C14—H14	119.9	C27—C28—H28B	120.0
C15—C14—H14	119.9	H28A—C28—H28B	120.0
C14—C15—C10	120.0 (2)	C1—N1—C3	109.62 (14)
C14—C15—H15	120.0	C1—N1—C16	117.89 (14)
C10—C15—H15	120.0	C3—N1—C16	131.04 (15)
N1—C16—C17	112.46 (14)	C1—N2—C2	109.85 (15)
N1—C16—H16A	109.1	C1—N2—C26	122.97 (16)
C17—C16—H16A	109.1	C2—N2—C26	126.32 (16)
N1—C16—H16B	109.1	C19—N3—O4	109.50 (14)
C17—C16—H16B	109.1	O6—N4—O5	123.0 (2)
H16A—C16—H16B	107.8	O6—N4—C23	118.8 (2)
O4—C17—C16	108.55 (14)	O5—N4—C23	118.2 (2)
O4—C17—C18	104.60 (14)	N3—O4—C17	107.87 (12)
C16—C17—C18	111.04 (15)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O1i	0.93	2.60	3.516 (2)	169
C18—H18B···O2ii	0.97	2.37	3.333 (2)	170
C26—H26B···O1i	0.97	2.55	3.379 (3)	144
C16—H16A···O2	0.97	2.10	2.902 (2)	141

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7⋯O1i	0.93	2.60	3.516 (2)	169
C18—H18B⋯O2ii	0.97	2.37	3.333 (2)	170
C26—H26B⋯O1i	0.97	2.55	3.379 (3)	144
C16—H16A⋯O2	0.97	2.10	2.902 (2)	141

Symmetry codes: (i) ; (ii) .