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

The mol-ecule of the title compound, C(29)H(20)N(2)O(3), contains four fused rings, three are six-membered rings and one is the five-membered imidazole ring. The fused-ring system is linked to two benzyl groups. The four fused rings are folded around the O=C⋯C=O direction of the anthraquinone, with a dihedral angle of 16.36 (8)° between the two terminal rings (A and D). The imidazole ring (D) is almost perpendicular to the two benzyl groups (E and F) with dihedral angles of 86.69 (17) and 83.15 (13)°, respectively. In the crystal, adjacent mol-ecules are linked by inter-molecular C-H⋯O hydrogen bonding.

Related literature

For background to the pharmacological activity of anthraquinone, see: Alves et al. (2004 ▶); Gatto et al. (1996 ▶); Krapcho et al. (1991 ▶). For information on its use as a synthetic dye, see: Naeimi & Namdari (2009 ▶). For related structures, see: Afrakssou et al. (2010 ▶); Guimarães et al. (2009 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C29H20N2O3

M = 444.47

Orthorhombic,

a = 8.1389 (3) Å

b = 12.8748 (4) Å

c = 21.5528 (8) Å

V = 2258.45 (14) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 296 K

0.49 × 0.18 × 0.15 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.982, T max = 0.987

36228 measured reflections

2629 independent reflections

2137 reflections with I > 2σ(I)

R int = 0.047

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.108

S = 1.05

2629 reflections

308 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.18 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: ORTEPIII (Burnett & Johnson, 1996 ▶) and ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811015078/dn2679sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811015078/dn2679Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811015078/dn2679Isup3.cml

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

C29H20N2O3	F(000) = 928
Mr = 444.47	Dx = 1.307 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2629 reflections
a = 8.1389 (3) Å	θ = 2.5–26.4°
b = 12.8748 (4) Å	µ = 0.09 mm−1
c = 21.5528 (8) Å	T = 296 K
V = 2258.45 (14) Å3	Flat, orange
Z = 4	0.49 × 0.18 × 0.15 mm

Bruker APEXII CCD diffractometer	2629 independent reflections
Radiation source: fine-focus sealed tube	2137 reflections with I > 2σ(I)
graphite	Rint = 0.047
φ and ω scans	θmax = 26.4°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −10→10
Tmin = 0.982, Tmax = 0.987	k = −15→16
36228 measured reflections	l = −26→26

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)] = 0.039	H-atom parameters constrained
wR(F2) = 0.108	w = 1/[σ2(Fo2) + (0.0603P)2 + 0.2421P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
2629 reflections	Δρmax = 0.23 e Å−3
308 parameters	Δρmin = −0.18 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: 0.0123 (15)

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.

	x	y	z	Uiso*/Ueq
C1	0.0570 (3)	0.41604 (19)	0.84012 (11)	0.0512 (6)
C2	0.2441 (3)	0.53761 (17)	0.81399 (10)	0.0420 (5)
C3	0.0919 (3)	0.58851 (17)	0.82177 (9)	0.0375 (5)
C4	0.0807 (3)	0.69572 (17)	0.81222 (9)	0.0387 (5)
C5	0.2294 (3)	0.74849 (19)	0.79858 (10)	0.0439 (5)
C6	0.3764 (3)	0.6961 (2)	0.79119 (12)	0.0508 (6)
H6	0.4711	0.7333	0.7818	0.061*
C7	0.3851 (3)	0.5888 (2)	0.79761 (11)	0.0503 (6)
H7	0.4829	0.5532	0.7910	0.060*
C8	−0.0748 (3)	0.75336 (18)	0.80889 (10)	0.0425 (5)
C9	−0.0669 (3)	0.86723 (18)	0.81962 (10)	0.0471 (6)
C10	0.0803 (3)	0.92029 (19)	0.81274 (10)	0.0507 (6)
C11	0.2320 (4)	0.8639 (2)	0.79481 (12)	0.0546 (6)
C12	0.0849 (5)	1.0278 (2)	0.82132 (12)	0.0674 (8)
H12	0.1826	1.0642	0.8158	0.081*
C13	−0.0569 (5)	1.0794 (2)	0.83799 (13)	0.0758 (9)
H13	−0.0538	1.1507	0.8449	0.091*
C14	−0.2029 (5)	1.0266 (2)	0.84455 (13)	0.0730 (9)
H14	−0.2975	1.0624	0.8558	0.088*
C15	−0.2100 (4)	0.9207 (2)	0.83451 (13)	0.0606 (7)
H15	−0.3095	0.8855	0.8377	0.073*
C16	−0.1814 (3)	0.5233 (2)	0.86850 (12)	0.0506 (6)
H16A	−0.2310	0.4552	0.8728	0.061*
H16B	−0.2530	0.5651	0.8426	0.061*
C17	−0.1677 (3)	0.5729 (2)	0.93142 (12)	0.0590 (7)
C18	−0.0688 (5)	0.5290 (4)	0.97586 (16)	0.1043 (13)
H18	−0.0091	0.4694	0.9667	0.125*
C19	−0.0579 (8)	0.5726 (6)	1.0333 (2)	0.155 (2)
H19	0.0095	0.5425	1.0631	0.186*
C20	−0.1443 (10)	0.6593 (6)	1.0473 (2)	0.164 (3)
H20	−0.1352	0.6888	1.0866	0.197*
C21	−0.2439 (9)	0.7032 (4)	1.0045 (3)	0.152 (3)
H21	−0.3042	0.7624	1.0140	0.183*
C22	−0.2544 (6)	0.6587 (3)	0.94659 (17)	0.1007 (13)
H22	−0.3230	0.6886	0.9171	0.121*
C23	0.3437 (3)	0.3524 (2)	0.82695 (13)	0.0583 (7)
H23A	0.4241	0.3652	0.7946	0.070*
H23B	0.2925	0.2859	0.8184	0.070*
C24	0.4309 (3)	0.34610 (19)	0.88834 (12)	0.0522 (6)
C25	0.5405 (5)	0.2681 (3)	0.8964 (2)	0.1062 (14)
H25	0.5582	0.2207	0.8645	0.127*
C26	0.6266 (7)	0.2583 (5)	0.9517 (3)	0.143 (2)
H26	0.7019	0.2045	0.9563	0.172*
C27	0.6028 (6)	0.3250 (4)	0.9984 (2)	0.1106 (15)
H27	0.6577	0.3162	1.0359	0.133*
C28	0.4987 (5)	0.4050 (3)	0.99050 (14)	0.0869 (10)
H28	0.4856	0.4536	1.0221	0.104*
C29	0.4106 (4)	0.4159 (2)	0.93574 (13)	0.0680 (8)
H29	0.3374	0.4709	0.9312	0.082*
N1	−0.0211 (2)	0.51260 (15)	0.83808 (8)	0.0440 (5)
N2	0.2183 (2)	0.43334 (15)	0.82446 (9)	0.0484 (5)
O1	−0.0047 (3)	0.33329 (14)	0.85284 (11)	0.0743 (6)
O2	0.3554 (3)	0.91046 (17)	0.77953 (12)	0.0851 (7)
O3	−0.2048 (2)	0.71168 (14)	0.79558 (9)	0.0562 (5)

	U11	U22	U33	U12	U13	U23
C1	0.0601 (15)	0.0381 (13)	0.0553 (13)	0.0009 (12)	−0.0041 (12)	−0.0057 (10)
C2	0.0419 (12)	0.0429 (12)	0.0412 (11)	0.0069 (10)	−0.0025 (10)	−0.0031 (9)
C3	0.0349 (11)	0.0410 (11)	0.0366 (10)	0.0006 (10)	−0.0014 (9)	−0.0027 (9)
C4	0.0382 (11)	0.0420 (12)	0.0358 (10)	0.0022 (10)	−0.0006 (9)	−0.0008 (9)
C5	0.0424 (13)	0.0459 (13)	0.0433 (12)	−0.0039 (11)	0.0011 (10)	0.0043 (10)
C6	0.0374 (12)	0.0613 (16)	0.0539 (13)	−0.0058 (12)	0.0048 (11)	0.0031 (12)
C7	0.0348 (12)	0.0621 (15)	0.0540 (13)	0.0065 (12)	0.0018 (10)	−0.0024 (12)
C8	0.0421 (12)	0.0444 (12)	0.0410 (11)	0.0045 (11)	−0.0014 (10)	0.0026 (9)
C9	0.0588 (14)	0.0397 (12)	0.0427 (12)	0.0091 (12)	−0.0023 (12)	0.0030 (9)
C10	0.0676 (16)	0.0409 (12)	0.0437 (12)	0.0020 (13)	−0.0013 (12)	0.0066 (10)
C11	0.0595 (16)	0.0503 (14)	0.0541 (14)	−0.0097 (13)	0.0074 (12)	0.0093 (12)
C12	0.103 (2)	0.0414 (14)	0.0578 (15)	−0.0049 (17)	−0.0003 (17)	0.0088 (12)
C13	0.130 (3)	0.0387 (13)	0.0591 (16)	0.016 (2)	0.0005 (19)	0.0022 (12)
C14	0.101 (3)	0.0517 (16)	0.0663 (17)	0.0253 (18)	0.0034 (17)	−0.0017 (13)
C15	0.0702 (17)	0.0507 (14)	0.0608 (15)	0.0181 (14)	0.0031 (14)	0.0013 (12)
C16	0.0371 (12)	0.0480 (13)	0.0666 (14)	−0.0062 (11)	0.0028 (11)	0.0018 (11)
C17	0.0514 (14)	0.0671 (16)	0.0586 (14)	−0.0085 (15)	0.0149 (12)	0.0018 (13)
C18	0.096 (3)	0.151 (4)	0.0661 (19)	0.017 (3)	−0.009 (2)	−0.003 (2)
C19	0.145 (5)	0.254 (8)	0.064 (2)	0.017 (6)	−0.012 (3)	−0.020 (3)
C20	0.203 (7)	0.214 (7)	0.076 (3)	−0.038 (6)	0.041 (4)	−0.055 (4)
C21	0.209 (7)	0.148 (5)	0.100 (3)	0.019 (5)	0.060 (4)	−0.043 (4)
C22	0.124 (3)	0.094 (3)	0.084 (2)	0.021 (3)	0.032 (2)	−0.010 (2)
C23	0.0621 (16)	0.0460 (13)	0.0666 (16)	0.0194 (13)	−0.0007 (14)	−0.0110 (12)
C24	0.0457 (13)	0.0493 (13)	0.0615 (14)	0.0066 (12)	0.0049 (12)	0.0079 (11)
C25	0.119 (3)	0.093 (3)	0.106 (3)	0.061 (3)	−0.024 (3)	−0.004 (2)
C26	0.148 (4)	0.148 (4)	0.133 (4)	0.082 (4)	−0.040 (4)	0.016 (4)
C27	0.092 (3)	0.152 (4)	0.087 (3)	0.008 (3)	−0.027 (2)	0.044 (3)
C28	0.093 (2)	0.111 (3)	0.0569 (17)	−0.014 (2)	−0.0090 (17)	0.0104 (17)
C29	0.0717 (19)	0.0707 (17)	0.0618 (16)	0.0085 (17)	−0.0029 (14)	0.0048 (14)
N1	0.0427 (11)	0.0397 (10)	0.0497 (10)	−0.0022 (9)	0.0009 (9)	−0.0037 (8)
N2	0.0468 (11)	0.0403 (11)	0.0582 (11)	0.0097 (9)	−0.0025 (10)	−0.0058 (9)
O1	0.0786 (14)	0.0369 (9)	0.1073 (17)	−0.0058 (10)	0.0062 (12)	−0.0017 (9)
O2	0.0745 (14)	0.0620 (12)	0.1188 (18)	−0.0200 (12)	0.0288 (14)	0.0139 (12)
O3	0.0412 (9)	0.0526 (10)	0.0749 (12)	0.0058 (8)	−0.0080 (8)	0.0012 (9)

C1—O1	1.209 (3)	C16—C17	1.503 (4)
C1—N2	1.374 (3)	C16—H16A	0.9700
C1—N1	1.397 (3)	C16—H16B	0.9700
C2—C7	1.370 (3)	C17—C22	1.351 (5)
C2—N2	1.377 (3)	C17—C18	1.373 (5)
C2—C3	1.412 (3)	C18—C19	1.362 (6)
C3—N1	1.387 (3)	C18—H18	0.9300
C3—C4	1.398 (3)	C19—C20	1.353 (9)
C4—C5	1.418 (3)	C19—H19	0.9300
C4—C8	1.469 (3)	C20—C21	1.353 (9)
C5—C6	1.383 (3)	C20—H20	0.9300
C5—C11	1.488 (4)	C21—C22	1.375 (7)
C6—C7	1.390 (4)	C21—H21	0.9300
C6—H6	0.9300	C22—H22	0.9300
C7—H7	0.9300	C23—N2	1.460 (3)
C8—O3	1.220 (3)	C23—C24	1.504 (4)
C8—C9	1.486 (3)	C23—H23A	0.9700
C9—C10	1.387 (4)	C23—H23B	0.9700
C9—C15	1.391 (4)	C24—C25	1.354 (4)
C10—C12	1.396 (4)	C24—C29	1.371 (4)
C10—C11	1.483 (4)	C25—C26	1.389 (6)
C11—O2	1.215 (3)	C25—H25	0.9300
C12—C13	1.380 (5)	C26—C27	1.338 (6)
C12—H12	0.9300	C26—H26	0.9300
C13—C14	1.376 (5)	C27—C28	1.344 (5)
C13—H13	0.9300	C27—H27	0.9300
C14—C15	1.382 (4)	C28—C29	1.388 (4)
C14—H14	0.9300	C28—H28	0.9300
C15—H15	0.9300	C29—H29	0.9300
C16—N1	1.467 (3)
O1—C1—N2	126.5 (2)	H16A—C16—H16B	107.9
O1—C1—N1	127.0 (2)	C22—C17—C18	118.3 (3)
N2—C1—N1	106.4 (2)	C22—C17—C16	121.8 (3)
C7—C2—N2	129.7 (2)	C18—C17—C16	119.9 (3)
C7—C2—C3	122.8 (2)	C19—C18—C17	120.2 (5)
N2—C2—C3	107.4 (2)	C19—C18—H18	119.9
N1—C3—C4	133.6 (2)	C17—C18—H18	119.9
N1—C3—C2	106.54 (18)	C20—C19—C18	120.6 (5)
C4—C3—C2	119.8 (2)	C20—C19—H19	119.7
C3—C4—C5	116.6 (2)	C18—C19—H19	119.7
C3—C4—C8	124.2 (2)	C21—C20—C19	120.2 (5)
C5—C4—C8	118.87 (18)	C21—C20—H20	119.9
C6—C5—C4	121.9 (2)	C19—C20—H20	119.9
C6—C5—C11	117.9 (2)	C20—C21—C22	118.9 (6)
C4—C5—C11	120.1 (2)	C20—C21—H21	120.6
C5—C6—C7	121.2 (2)	C22—C21—H21	120.6
C5—C6—H6	119.4	C17—C22—C21	121.8 (5)
C7—C6—H6	119.4	C17—C22—H22	119.1
C2—C7—C6	117.5 (2)	C21—C22—H22	119.1
C2—C7—H7	121.3	N2—C23—C24	113.6 (2)
C6—C7—H7	121.3	N2—C23—H23A	108.8
O3—C8—C4	122.4 (2)	C24—C23—H23A	108.8
O3—C8—C9	120.5 (2)	N2—C23—H23B	108.8
C4—C8—C9	117.0 (2)	C24—C23—H23B	108.8
C10—C9—C15	120.3 (2)	H23A—C23—H23B	107.7
C10—C9—C8	120.5 (2)	C25—C24—C29	118.0 (3)
C15—C9—C8	119.2 (2)	C25—C24—C23	117.6 (3)
C9—C10—C12	119.8 (3)	C29—C24—C23	124.3 (2)
C9—C10—C11	120.4 (2)	C24—C25—C26	120.7 (4)
C12—C10—C11	119.8 (3)	C24—C25—H25	119.7
O2—C11—C10	121.1 (2)	C26—C25—H25	119.7
O2—C11—C5	121.3 (3)	C27—C26—C25	120.9 (4)
C10—C11—C5	117.5 (2)	C27—C26—H26	119.5
C13—C12—C10	119.3 (3)	C25—C26—H26	119.5
C13—C12—H12	120.4	C26—C27—C28	119.2 (4)
C10—C12—H12	120.4	C26—C27—H27	120.4
C14—C13—C12	120.8 (3)	C28—C27—H27	120.4
C14—C13—H13	119.6	C27—C28—C29	120.7 (4)
C12—C13—H13	119.6	C27—C28—H28	119.6
C13—C14—C15	120.5 (3)	C29—C28—H28	119.6
C13—C14—H14	119.8	C24—C29—C28	120.3 (3)
C15—C14—H14	119.8	C24—C29—H29	119.8
C14—C15—C9	119.3 (3)	C28—C29—H29	119.8
C14—C15—H15	120.4	C3—N1—C1	109.50 (19)
C9—C15—H15	120.4	C3—N1—C16	129.55 (19)
N1—C16—C17	112.2 (2)	C1—N1—C16	118.3 (2)
N1—C16—H16A	109.2	C1—N2—C2	110.11 (19)
C17—C16—H16A	109.2	C1—N2—C23	122.9 (2)
N1—C16—H16B	109.2	C2—N2—C23	126.6 (2)
C17—C16—H16B	109.2

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···O1i	0.93	2.39	3.312 (3)	171.
C23—H23A···O2ii	0.97	2.47	3.439 (4)	174.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13⋯O1i	0.93	2.39	3.312 (3)	171
C23—H23A⋯O2ii	0.97	2.47	3.439 (4)	174

Symmetry codes: (i) ; (ii) .