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

In the title compound, C(21)H(16)N(2)O(3), the fused-ring system (r.m.s. deviation = 0.067 Å) is slightly buckled at the carbonyl C atom of the anthracenyl ring system [deviation = 0.177 (1) Å] that is closer to an allyl substituent. The two allyl units lie on the same side of the fused-ring plane but are oriented in opposite directions, with N-C-C-C torsion angles of 126.9 (2) and 116.7 (2)°. In the crystal, the mol-ecules are linked into chains propagating along the b axis by C-H⋯O hydrogen bonds.

Related literature

For a related structure, see: Guimarães et al. (2009 ▶).

Experimental

Crystal data

C21H16N2O3

M = 344.36

Monoclinic,

a = 7.8539 (2) Å

b = 11.5822 (3) Å

c = 18.1455 (4) Å

β = 93.537 (1)°

V = 1647.47 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.40 × 0.35 × 0.20 mm

Data collection

Bruker X8 APEXII area-detector diffractometer

22612 measured reflections

4806 independent reflections 4805 in Refinement?

3053 reflections with I > 2σ(I)

R int = 0.039

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.153

S = 1.02

4805 reflections

236 parameters

H-atom parameters constrained

Δρmax = 0.31 e Å−3

Δρmin = −0.22 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810024748/ci5112sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810024748/ci5112Isup2.hkl

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

C21H16N2O3	F(000) = 720
Mr = 344.36	Dx = 1.388 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4815 reflections
a = 7.8539 (2) Å	θ = 2.2–29.4°
b = 11.5822 (3) Å	µ = 0.09 mm−1
c = 18.1455 (4) Å	T = 293 K
β = 93.537 (1)°	Block, orange
V = 1647.47 (7) Å3	0.40 × 0.35 × 0.20 mm
Z = 4

Bruker X8 APEXII area-detector diffractometer	3053 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.039
graphite	θmax = 30.0°, θmin = 2.1°
φ and ω scans	h = −11→11
22612 measured reflections	k = −16→16
4806 independent reflections	l = −25→25

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)] = 0.049	H-atom parameters constrained
wR(F2) = 0.153	w = 1/[σ2(Fo2) + (0.0755P)2 + 0.2066P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max = 0.001
4805 reflections	Δρmax = 0.31 e Å−3
236 parameters	Δρmin = −0.22 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: 0.0033 (11)

	x	y	z	Uiso*/Ueq
O1	0.14067 (16)	0.31774 (10)	0.53905 (6)	0.0588 (3)
O2	0.23915 (17)	0.77316 (10)	0.53322 (7)	0.0623 (3)
O3	0.44816 (18)	0.19062 (10)	0.30395 (6)	0.0633 (4)
N1	0.35081 (16)	0.29295 (10)	0.40381 (6)	0.0405 (3)
N2	0.42897 (16)	0.38962 (10)	0.30579 (6)	0.0422 (3)
C1	0.32994 (17)	0.40923 (11)	0.41903 (7)	0.0342 (3)
C2	0.27111 (16)	0.47213 (11)	0.47863 (7)	0.0342 (3)
C3	0.18650 (18)	0.41799 (12)	0.54058 (7)	0.0387 (3)
C4	0.14672 (17)	0.49192 (13)	0.60472 (8)	0.0408 (3)
C5	0.0848 (2)	0.43992 (15)	0.66656 (9)	0.0532 (4)
H5	0.0729	0.3601	0.6683	0.064*
C6	0.0408 (2)	0.50686 (19)	0.72553 (9)	0.0635 (5)
H6	−0.0001	0.4719	0.7671	0.076*
C7	0.0572 (2)	0.62479 (19)	0.72301 (10)	0.0649 (5)
H7	0.0265	0.6693	0.7627	0.078*
C8	0.1187 (2)	0.67763 (16)	0.66225 (10)	0.0557 (4)
H8	0.1301	0.7575	0.6610	0.067*
C9	0.16416 (18)	0.61104 (13)	0.60235 (8)	0.0427 (3)
C10	0.22782 (18)	0.66824 (13)	0.53631 (8)	0.0428 (3)
C11	0.27960 (17)	0.59389 (12)	0.47464 (7)	0.0372 (3)
C12	0.3362 (2)	0.64983 (13)	0.41289 (8)	0.0443 (3)
H12	0.3403	0.7301	0.4122	0.053*
C13	0.38660 (19)	0.58851 (12)	0.35255 (8)	0.0437 (3)
H13	0.4219	0.6261	0.3108	0.052*
C14	0.38263 (17)	0.47023 (12)	0.35652 (7)	0.0368 (3)
C15	0.4124 (2)	0.28065 (13)	0.33395 (8)	0.0451 (4)
C16	0.4861 (2)	0.40982 (14)	0.23155 (7)	0.0462 (4)
H16A	0.5829	0.3603	0.2237	0.055*
H16B	0.5234	0.4893	0.2277	0.055*
C17	0.3483 (2)	0.38657 (17)	0.17310 (9)	0.0595 (5)
H17	0.3070	0.3114	0.1688	0.071*
C18	0.2826 (3)	0.4620 (2)	0.12858 (11)	0.0851 (7)
H18A	0.3206	0.5380	0.1312	0.102*
H18B	0.1969	0.4409	0.0935	0.102*
C19	0.3537 (2)	0.18926 (12)	0.45100 (8)	0.0431 (3)
H19A	0.3615	0.2133	0.5023	0.052*
H19B	0.4552	0.1448	0.4424	0.052*
C20	0.2018 (2)	0.11366 (14)	0.43818 (8)	0.0498 (4)
H20	0.0939	0.1461	0.4403	0.060*
C21	0.2140 (3)	0.00335 (17)	0.42404 (11)	0.0695 (5)
H21A	0.3207	−0.0307	0.4217	0.083*
H21B	0.1158	−0.0411	0.4163	0.083*

	U11	U22	U33	U12	U13	U23
O1	0.0796 (8)	0.0408 (6)	0.0591 (7)	−0.0081 (6)	0.0298 (6)	−0.0009 (5)
O2	0.0821 (9)	0.0354 (6)	0.0711 (8)	−0.0067 (6)	0.0191 (6)	−0.0114 (5)
O3	0.1046 (10)	0.0388 (6)	0.0494 (7)	0.0101 (6)	0.0285 (6)	−0.0027 (5)
N1	0.0577 (7)	0.0304 (6)	0.0343 (6)	0.0046 (5)	0.0110 (5)	0.0026 (4)
N2	0.0573 (7)	0.0374 (6)	0.0330 (6)	0.0023 (5)	0.0113 (5)	0.0013 (5)
C1	0.0386 (7)	0.0309 (6)	0.0332 (6)	0.0013 (5)	0.0033 (5)	0.0014 (5)
C2	0.0356 (7)	0.0342 (7)	0.0327 (6)	0.0008 (5)	0.0021 (5)	0.0006 (5)
C3	0.0418 (7)	0.0374 (7)	0.0373 (7)	0.0022 (6)	0.0067 (6)	0.0014 (6)
C4	0.0381 (7)	0.0484 (8)	0.0363 (7)	0.0042 (6)	0.0048 (6)	−0.0015 (6)
C5	0.0589 (10)	0.0575 (10)	0.0447 (8)	0.0056 (8)	0.0151 (7)	0.0033 (7)
C6	0.0697 (11)	0.0793 (13)	0.0434 (9)	0.0053 (10)	0.0189 (8)	−0.0030 (9)
C7	0.0712 (12)	0.0783 (14)	0.0465 (9)	0.0071 (10)	0.0143 (8)	−0.0192 (9)
C8	0.0608 (10)	0.0552 (10)	0.0518 (9)	0.0046 (8)	0.0077 (8)	−0.0152 (8)
C9	0.0399 (7)	0.0472 (8)	0.0409 (7)	0.0030 (6)	0.0024 (6)	−0.0077 (6)
C10	0.0443 (8)	0.0376 (8)	0.0466 (8)	−0.0008 (6)	0.0034 (6)	−0.0079 (6)
C11	0.0395 (7)	0.0330 (7)	0.0392 (7)	0.0004 (5)	0.0028 (6)	−0.0015 (5)
C12	0.0560 (9)	0.0311 (7)	0.0462 (8)	−0.0028 (6)	0.0064 (7)	0.0023 (6)
C13	0.0548 (9)	0.0366 (7)	0.0404 (7)	−0.0025 (6)	0.0087 (6)	0.0061 (6)
C14	0.0408 (7)	0.0361 (7)	0.0339 (7)	0.0010 (6)	0.0052 (5)	0.0013 (5)
C15	0.0618 (9)	0.0382 (8)	0.0365 (7)	0.0053 (7)	0.0123 (7)	0.0003 (6)
C16	0.0564 (9)	0.0479 (8)	0.0360 (7)	−0.0006 (7)	0.0158 (6)	0.0019 (6)
C17	0.0686 (11)	0.0708 (12)	0.0406 (8)	−0.0083 (9)	0.0168 (8)	−0.0026 (8)
C18	0.0780 (14)	0.131 (2)	0.0468 (10)	0.0076 (13)	0.0107 (9)	0.0108 (12)
C19	0.0573 (9)	0.0331 (7)	0.0394 (7)	0.0057 (6)	0.0076 (6)	0.0057 (6)
C20	0.0611 (10)	0.0430 (8)	0.0458 (8)	0.0004 (7)	0.0067 (7)	0.0062 (7)
C21	0.0869 (13)	0.0486 (10)	0.0739 (13)	−0.0104 (10)	0.0114 (10)	−0.0024 (9)

O1—C3	1.2154 (18)	C8—H8	0.93
O2—C10	1.2200 (18)	C9—C10	1.483 (2)
O3—C15	1.2170 (17)	C10—C11	1.4884 (19)
N1—C1	1.3867 (16)	C11—C12	1.3908 (19)
N1—C15	1.3918 (18)	C12—C13	1.383 (2)
N1—C19	1.4742 (17)	C12—H12	0.93
N2—C15	1.3708 (19)	C13—C14	1.372 (2)
N2—C14	1.3757 (17)	C13—H13	0.93
N2—C16	1.4647 (17)	C16—C17	1.493 (2)
C1—C2	1.4056 (18)	C16—H16A	0.97
C1—C14	1.4194 (18)	C16—H16B	0.97
C2—C11	1.4139 (19)	C17—C18	1.277 (3)
C2—C3	1.4800 (18)	C17—H17	0.93
C3—C4	1.4934 (19)	C18—H18A	0.93
C4—C9	1.387 (2)	C18—H18B	0.93
C4—C5	1.388 (2)	C19—C20	1.486 (2)
C5—C6	1.382 (2)	C19—H19A	0.97
C5—H5	0.93	C19—H19B	0.97
C6—C7	1.373 (3)	C20—C21	1.308 (2)
C6—H6	0.93	C20—H20	0.93
C7—C8	1.375 (3)	C21—H21A	0.93
C7—H7	0.93	C21—H21B	0.93
C8—C9	1.397 (2)
C1—N1—C15	109.44 (11)	C2—C11—C10	121.50 (12)
C1—N1—C19	132.32 (11)	C13—C12—C11	121.32 (13)
C15—N1—C19	116.86 (11)	C13—C12—H12	119.3
C15—N2—C14	109.90 (11)	C11—C12—H12	119.3
C15—N2—C16	122.09 (12)	C14—C13—C12	117.55 (13)
C14—N2—C16	128.00 (12)	C14—C13—H13	121.2
N1—C1—C2	134.84 (12)	C12—C13—H13	121.2
N1—C1—C14	106.28 (11)	C13—C14—N2	129.39 (13)
C2—C1—C14	118.87 (12)	C13—C14—C1	123.19 (13)
C1—C2—C11	117.30 (12)	N2—C14—C1	107.40 (12)
C1—C2—C3	123.31 (12)	O3—C15—N2	126.33 (14)
C11—C2—C3	119.10 (12)	O3—C15—N1	126.71 (14)
O1—C3—C2	122.25 (13)	N2—C15—N1	106.95 (12)
O1—C3—C4	119.32 (13)	N2—C16—C17	112.01 (13)
C2—C3—C4	118.31 (12)	N2—C16—H16A	109.2
C9—C4—C5	119.78 (14)	C17—C16—H16A	109.2
C9—C4—C3	121.35 (13)	N2—C16—H16B	109.2
C5—C4—C3	118.81 (14)	C17—C16—H16B	109.2
C6—C5—C4	119.96 (17)	H16A—C16—H16B	107.9
C6—C5—H5	120.0	C18—C17—C16	125.0 (2)
C4—C5—H5	120.0	C18—C17—H17	117.5
C7—C6—C5	120.24 (17)	C16—C17—H17	117.5
C7—C6—H6	119.9	C17—C18—H18A	120.0
C5—C6—H6	119.9	C17—C18—H18B	120.0
C6—C7—C8	120.54 (16)	H18A—C18—H18B	120.0
C6—C7—H7	119.7	N1—C19—C20	113.92 (13)
C8—C7—H7	119.7	N1—C19—H19A	108.8
C7—C8—C9	119.83 (18)	C20—C19—H19A	108.8
C7—C8—H8	120.1	N1—C19—H19B	108.8
C9—C8—H8	120.1	C20—C19—H19B	108.8
C4—C9—C8	119.64 (15)	H19A—C19—H19B	107.7
C4—C9—C10	120.54 (13)	C21—C20—C19	122.60 (17)
C8—C9—C10	119.81 (15)	C21—C20—H20	118.7
O2—C10—C9	120.76 (13)	C19—C20—H20	118.7
O2—C10—C11	121.17 (14)	C20—C21—H21A	120.0
C9—C10—C11	118.07 (13)	C20—C21—H21B	120.0
C12—C11—C2	121.62 (13)	H21A—C21—H21B	120.0
C12—C11—C10	116.87 (13)
C15—N1—C1—C2	178.83 (15)	C1—C2—C11—C10	−177.23 (12)
C19—N1—C1—C2	−15.3 (3)	C3—C2—C11—C10	8.7 (2)
C15—N1—C1—C14	−0.69 (16)	O2—C10—C11—C12	−1.9 (2)
C19—N1—C1—C14	165.13 (14)	C9—C10—C11—C12	179.00 (13)
N1—C1—C2—C11	176.13 (15)	O2—C10—C11—C2	178.30 (14)
C14—C1—C2—C11	−4.39 (18)	C9—C10—C11—C2	−0.8 (2)
N1—C1—C2—C3	−10.1 (2)	C2—C11—C12—C13	0.1 (2)
C14—C1—C2—C3	169.38 (12)	C10—C11—C12—C13	−179.75 (14)
C1—C2—C3—O1	−10.6 (2)	C11—C12—C13—C14	−1.6 (2)
C11—C2—C3—O1	163.09 (14)	C12—C13—C14—N2	−178.38 (14)
C1—C2—C3—C4	173.42 (12)	C12—C13—C14—C1	−0.1 (2)
C11—C2—C3—C4	−12.91 (19)	C15—N2—C14—C13	176.95 (15)
O1—C3—C4—C9	−166.55 (14)	C16—N2—C14—C13	−3.9 (3)
C2—C3—C4—C9	9.6 (2)	C15—N2—C14—C1	−1.58 (16)
O1—C3—C4—C5	10.9 (2)	C16—N2—C14—C1	177.55 (14)
C2—C3—C4—C5	−172.99 (13)	N1—C1—C14—C13	−177.27 (13)
C9—C4—C5—C6	0.0 (2)	C2—C1—C14—C13	3.1 (2)
C3—C4—C5—C6	−177.51 (15)	N1—C1—C14—N2	1.38 (15)
C4—C5—C6—C7	0.4 (3)	C2—C1—C14—N2	−178.24 (12)
C5—C6—C7—C8	−0.5 (3)	C14—N2—C15—O3	−177.54 (17)
C6—C7—C8—C9	0.3 (3)	C16—N2—C15—O3	3.3 (3)
C5—C4—C9—C8	−0.2 (2)	C14—N2—C15—N1	1.15 (17)
C3—C4—C9—C8	177.27 (14)	C16—N2—C15—N1	−178.04 (13)
C5—C4—C9—C10	−179.13 (14)	C1—N1—C15—O3	178.43 (16)
C3—C4—C9—C10	−1.7 (2)	C19—N1—C15—O3	10.1 (3)
C7—C8—C9—C4	0.0 (2)	C1—N1—C15—N2	−0.26 (18)
C7—C8—C9—C10	178.99 (15)	C19—N1—C15—N2	−168.54 (12)
C4—C9—C10—O2	178.08 (14)	C15—N2—C16—C17	76.63 (19)
C8—C9—C10—O2	−0.9 (2)	C14—N2—C16—C17	−102.40 (18)
C4—C9—C10—C11	−2.8 (2)	N2—C16—C17—C18	116.73 (19)
C8—C9—C10—C11	178.24 (14)	C1—N1—C19—C20	109.60 (18)
C1—C2—C11—C12	2.9 (2)	C15—N1—C19—C20	−85.41 (17)
C3—C2—C11—C12	−171.10 (13)	N1—C19—C20—C21	126.87 (17)

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···O3i	0.93	2.49	3.406 (2)	168
C16—H16B···O3i	0.97	2.42	3.362 (2)	165

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13⋯O3i	0.93	2.49	3.406 (2)	168
C16—H16B⋯O3i	0.97	2.42	3.362 (2)	165

Symmetry code: (i) .