1,3-Bis(prop-2-yn-1-yl)-1H-anthra[1,2-d]imidazole-2,6,11(3H)-trione.

In the title compound, C21H12N2O3, the fused-ring system is roughly planar, the largest deviation from the mean plane being 0.084 (2) Å. The two prop-2-yn-1-yl groups are almost perpendicular to the fused ring plane, making C-C-N-C torsion angles of -103.4 (2) and -105.3 (2)°, and point in opposite directions with respect to the plane. In the crystal, mol-ecules are linked by weak C-H⋯O hydrogen bonds, forming a three-dimensional network.

Related literature

For background to the pharmacological activity and potential applications of anthra­quinones, see: Alves et al. (2004 ▶); Ellis et al. (2003 ▶); Boseggia et al. (2004 ▶); Mariappan & Basa (2011 ▶); Kadarkaraisamy et al. (2008 ▶). For similar compounds, see: Afrakssou et al. (2010 ▶, 2011 ▶); Guimarães et al. (2009 ▶).

Experimental

Crystal data

C21H12N2O3

M = 340.33

Monoclinic,

a = 16.6972 (5) Å

b = 4.5602 (1) Å

c = 21.2500 (5) Å

β = 96.352 (2)°

V = 1608.10 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 296 K

0.46 × 0.14 × 0.05 mm

Data collection

Bruker APEXII CCD diffractometer

20426 measured reflections

3177 independent reflections

2301 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.129

S = 1.02

3177 reflections

235 parameters

H-atom parameters constrained

Δρmax = 0.33 e Å−3

Δρmin = −0.25 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT-Plus (Bruker, 2009 ▶); data reduction: SAIn class="Chemical">NT-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 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813013688/im2432sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813013688/im2432Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813013688/im2432Isup3.cml

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

C21H12N2O3	F(000) = 704
Mr = 340.33	Dx = 1.406 Mg m−3
Monoclinic, P21/c	Melting point: 463 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 16.6972 (5) Å	Cell parameters from 3177 reflections
b = 4.5602 (1) Å	θ = 2.5–26.0°
c = 21.2500 (5) Å	µ = 0.10 mm−1
β = 96.352 (2)°	T = 296 K
V = 1608.10 (7) Å3	Irregular shape, yellow
Z = 4	0.46 × 0.14 × 0.05 mm

Bruker APEXII CCD diffractometer	2301 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.033
Graphite monochromator	θmax = 26.0°, θmin = 2.4°
φ and ω scans	h = −20→19
20426 measured reflections	k = −5→5
3177 independent reflections	l = −26→25

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)] = 0.044	Hydrogen site location: difference Fourier map
wR(F2) = 0.129	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0555P)2 + 0.5235P] where P = (Fo2 + 2Fc2)/3
3177 reflections	(Δ/σ)max < 0.001
235 parameters	Δρmax = 0.33 e Å−3
0 restraints	Δρmin = −0.25 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 > 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	0.27182 (12)	0.6098 (4)	0.40077 (9)	0.0604 (5)
C2	0.28450 (15)	0.4803 (6)	0.46051 (10)	0.0812 (7)
H2	0.2480	0.3427	0.4725	0.097*
C3	0.35059 (19)	0.5550 (7)	0.50163 (11)	0.0980 (9)
H3	0.3581	0.4711	0.5417	0.118*
C4	0.40550 (18)	0.7526 (7)	0.48372 (12)	0.1005 (9)
H4	0.4507	0.7995	0.5115	0.121*
C5	0.39427 (14)	0.8828 (6)	0.42474 (10)	0.0811 (7)
H5	0.4320	1.0164	0.4130	0.097*
C6	0.32708 (12)	0.8154 (4)	0.38289 (8)	0.0581 (5)
C7	0.31375 (10)	0.9681 (4)	0.32094 (8)	0.0521 (5)
C8	0.24435 (9)	0.8852 (4)	0.27529 (8)	0.0447 (4)
C9	0.18813 (10)	0.6776 (4)	0.29414 (8)	0.0505 (4)
C10	0.20212 (12)	0.5247 (4)	0.35604 (9)	0.0595 (5)
C11	0.22732 (9)	1.0111 (4)	0.21489 (8)	0.0444 (4)
C12	0.15499 (10)	0.9328 (4)	0.17752 (8)	0.0500 (4)
C13	0.09989 (11)	0.7381 (4)	0.19747 (10)	0.0596 (5)
H13	0.0521	0.6955	0.1723	0.072*
C14	0.11783 (11)	0.6094 (4)	0.25560 (10)	0.0603 (5)
H14	0.0822	0.4735	0.2696	0.072*
C15	0.21803 (11)	1.2631 (4)	0.12116 (9)	0.0551 (5)
C16	0.09096 (12)	1.0549 (5)	0.06690 (9)	0.0677 (6)
H16A	0.0776	0.8490	0.0610	0.081*
H16B	0.1133	1.1226	0.0293	0.081*
C17	0.01719 (12)	1.2201 (5)	0.07407 (9)	0.0592 (5)
C18	−0.04129 (13)	1.3540 (5)	0.07967 (11)	0.0738 (6)
H18	−0.0878	1.4604	0.0841	0.089*
C19	0.34510 (10)	1.3565 (4)	0.18615 (9)	0.0546 (5)
H19A	0.3465	1.5073	0.1541	0.066*
H19B	0.3530	1.4511	0.2272	0.066*
C20	0.41099 (11)	1.1519 (4)	0.18097 (9)	0.0565 (5)
C21	0.46571 (13)	0.9943 (6)	0.17751 (11)	0.0821 (7)
H21	0.5092	0.8691	0.1748	0.099*
N1	0.15159 (9)	1.0865 (4)	0.12144 (7)	0.0558 (4)
N2	0.26525 (8)	1.2155 (3)	0.17856 (7)	0.0482 (4)
O1	0.35778 (9)	1.1731 (4)	0.31003 (6)	0.0812 (5)
O2	0.15706 (10)	0.3264 (3)	0.36931 (8)	0.0825 (5)
O3	0.23256 (9)	1.4307 (4)	0.07918 (6)	0.0718 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0692 (12)	0.0584 (12)	0.0556 (11)	0.0081 (10)	0.0164 (9)	−0.0032 (9)
C2	0.1003 (18)	0.0830 (16)	0.0623 (13)	0.0040 (14)	0.0186 (13)	0.0081 (12)
C3	0.126 (2)	0.107 (2)	0.0583 (14)	0.0071 (19)	−0.0008 (15)	0.0138 (14)
C4	0.108 (2)	0.119 (2)	0.0669 (15)	−0.0052 (19)	−0.0214 (14)	0.0100 (16)
C5	0.0779 (15)	0.0963 (18)	0.0649 (13)	−0.0095 (13)	−0.0110 (11)	0.0053 (13)
C6	0.0610 (11)	0.0617 (12)	0.0516 (10)	0.0051 (10)	0.0058 (8)	−0.0054 (9)
C7	0.0453 (10)	0.0593 (11)	0.0525 (10)	−0.0035 (9)	0.0084 (8)	−0.0054 (9)
C8	0.0409 (9)	0.0431 (9)	0.0511 (9)	0.0031 (7)	0.0096 (7)	−0.0088 (8)
C9	0.0474 (10)	0.0460 (10)	0.0600 (10)	0.0002 (8)	0.0138 (8)	−0.0108 (9)
C10	0.0631 (12)	0.0512 (11)	0.0681 (12)	0.0017 (9)	0.0243 (10)	−0.0045 (10)
C11	0.0377 (8)	0.0418 (9)	0.0541 (9)	0.0030 (7)	0.0073 (7)	−0.0110 (8)
C12	0.0442 (9)	0.0505 (10)	0.0548 (10)	0.0048 (8)	0.0028 (7)	−0.0144 (9)
C13	0.0439 (10)	0.0633 (12)	0.0702 (12)	−0.0056 (9)	0.0003 (8)	−0.0207 (10)
C14	0.0505 (10)	0.0568 (11)	0.0754 (13)	−0.0096 (9)	0.0145 (9)	−0.0127 (10)
C15	0.0545 (11)	0.0581 (11)	0.0528 (10)	0.0102 (9)	0.0059 (8)	−0.0075 (10)
C16	0.0679 (13)	0.0758 (14)	0.0558 (11)	0.0085 (11)	−0.0094 (9)	−0.0183 (10)
C17	0.0515 (11)	0.0669 (13)	0.0565 (10)	−0.0073 (10)	−0.0066 (8)	−0.0058 (10)
C18	0.0527 (12)	0.0854 (16)	0.0807 (14)	−0.0005 (12)	−0.0038 (10)	−0.0060 (13)
C19	0.0516 (10)	0.0524 (11)	0.0604 (10)	−0.0036 (8)	0.0082 (8)	0.0000 (9)
C20	0.0461 (10)	0.0659 (12)	0.0573 (10)	−0.0024 (9)	0.0049 (8)	−0.0042 (10)
C21	0.0526 (12)	0.1004 (18)	0.0918 (16)	0.0151 (13)	0.0003 (11)	−0.0172 (14)
N1	0.0493 (9)	0.0611 (10)	0.0550 (9)	0.0049 (7)	−0.0038 (7)	−0.0128 (8)
N2	0.0423 (8)	0.0501 (8)	0.0519 (8)	0.0013 (6)	0.0036 (6)	−0.0032 (7)
O1	0.0712 (9)	0.1062 (13)	0.0632 (8)	−0.0379 (9)	−0.0060 (7)	0.0079 (8)
O2	0.0878 (11)	0.0711 (10)	0.0930 (11)	−0.0163 (9)	0.0289 (9)	0.0080 (9)
O3	0.0808 (10)	0.0764 (10)	0.0579 (8)	0.0050 (8)	0.0058 (7)	0.0079 (8)

C1—C2	1.395 (3)	C12—N1	1.378 (2)
C1—C6	1.397 (3)	C12—C13	1.379 (3)
C1—C10	1.471 (3)	C13—C14	1.370 (3)
C2—C3	1.373 (3)	C13—H13	0.9300
C2—H2	0.9300	C14—H14	0.9300
C3—C4	1.369 (4)	C15—O3	1.219 (2)
C3—H3	0.9300	C15—N1	1.371 (2)
C4—C5	1.381 (3)	C15—N2	1.394 (2)
C4—H4	0.9300	C16—N1	1.459 (2)
C5—C6	1.387 (3)	C16—C17	1.466 (3)
C5—H5	0.9300	C16—H16A	0.9700
C6—C7	1.484 (3)	C16—H16B	0.9700
C7—O1	1.227 (2)	C17—C18	1.169 (3)
C7—C8	1.476 (2)	C18—H18	0.9300
C8—C11	1.406 (2)	C19—C20	1.456 (3)
C8—C9	1.421 (2)	C19—N2	1.473 (2)
C9—C14	1.390 (3)	C19—H19A	0.9700
C9—C10	1.484 (3)	C19—H19B	0.9700
C10—O2	1.229 (2)	C20—C21	1.171 (3)
C11—N2	1.405 (2)	C21—H21	0.9300
C11—C12	1.416 (2)
C2—C1—C6	119.6 (2)	N1—C12—C11	107.92 (16)
C2—C1—C10	120.4 (2)	C13—C12—C11	123.15 (18)
C6—C1—C10	120.03 (18)	C14—C13—C12	117.79 (17)
C3—C2—C1	120.3 (2)	C14—C13—H13	121.1
C3—C2—H2	119.9	C12—C13—H13	121.1
C1—C2—H2	119.9	C13—C14—C9	121.41 (18)
C4—C3—C2	120.2 (2)	C13—C14—H14	119.3
C4—C3—H3	119.9	C9—C14—H14	119.3
C2—C3—H3	119.9	O3—C15—N1	126.71 (18)
C3—C4—C5	120.5 (2)	O3—C15—N2	126.79 (18)
C3—C4—H4	119.8	N1—C15—N2	106.50 (16)
C5—C4—H4	119.8	N1—C16—C17	112.56 (15)
C4—C5—C6	120.4 (2)	N1—C16—H16A	109.1
C4—C5—H5	119.8	C17—C16—H16A	109.1
C6—C5—H5	119.8	N1—C16—H16B	109.1
C5—C6—C1	119.07 (19)	C17—C16—H16B	109.1
C5—C6—C7	119.76 (19)	H16A—C16—H16B	107.8
C1—C6—C7	121.15 (17)	C18—C17—C16	179.4 (3)
O1—C7—C8	120.95 (17)	C17—C18—H18	180.0
O1—C7—C6	119.40 (17)	C20—C19—N2	113.23 (15)
C8—C7—C6	119.51 (16)	C20—C19—H19A	108.9
C11—C8—C9	117.12 (15)	N2—C19—H19A	108.9
C11—C8—C7	124.07 (15)	C20—C19—H19B	108.9
C9—C8—C7	118.71 (16)	N2—C19—H19B	108.9
C14—C9—C8	121.60 (18)	H19A—C19—H19B	107.7
C14—C9—C10	117.17 (17)	C21—C20—C19	177.8 (2)
C8—C9—C10	121.23 (16)	C20—C21—H21	180.0
O2—C10—C1	120.4 (2)	C15—N1—C12	110.27 (15)
O2—C10—C9	120.58 (19)	C15—N1—C16	123.02 (17)
C1—C10—C9	118.97 (17)	C12—N1—C16	126.52 (17)
N2—C11—C8	135.60 (15)	C15—N2—C11	109.78 (14)
N2—C11—C12	105.52 (15)	C15—N2—C19	116.43 (15)
C8—C11—C12	118.87 (16)	C11—N2—C19	133.40 (14)
N1—C12—C13	128.92 (16)
C6—C1—C2—C3	0.3 (3)	C9—C8—C11—C12	2.0 (2)
C10—C1—C2—C3	178.5 (2)	C7—C8—C11—C12	−174.30 (15)
C1—C2—C3—C4	−1.4 (4)	N2—C11—C12—N1	0.18 (18)
C2—C3—C4—C5	1.2 (5)	C8—C11—C12—N1	179.18 (14)
C3—C4—C5—C6	0.1 (4)	N2—C11—C12—C13	−178.94 (15)
C4—C5—C6—C1	−1.3 (4)	C8—C11—C12—C13	0.1 (3)
C4—C5—C6—C7	177.0 (2)	N1—C12—C13—C14	179.16 (18)
C2—C1—C6—C5	1.0 (3)	C11—C12—C13—C14	−1.9 (3)
C10—C1—C6—C5	−177.15 (19)	C12—C13—C14—C9	1.7 (3)
C2—C1—C6—C7	−177.14 (18)	C8—C9—C14—C13	0.4 (3)
C10—C1—C6—C7	4.7 (3)	C10—C9—C14—C13	−179.65 (17)
C5—C6—C7—O1	−7.3 (3)	N1—C16—C17—C18	78 (22)
C1—C6—C7—O1	170.83 (18)	N2—C19—C20—C21	−169 (100)
C5—C6—C7—C8	176.98 (18)	O3—C15—N1—C12	−178.55 (18)
C1—C6—C7—C8	−4.8 (3)	N2—C15—N1—C12	0.87 (19)
O1—C7—C8—C11	5.9 (3)	O3—C15—N1—C16	6.1 (3)
C6—C7—C8—C11	−178.50 (16)	N2—C15—N1—C16	−174.45 (15)
O1—C7—C8—C9	−170.35 (17)	C13—C12—N1—C15	178.39 (17)
C6—C7—C8—C9	5.3 (2)	C11—C12—N1—C15	−0.67 (19)
C11—C8—C9—C14	−2.3 (2)	C13—C12—N1—C16	−6.5 (3)
C7—C8—C9—C14	174.22 (16)	C11—C12—N1—C16	174.46 (16)
C11—C8—C9—C10	177.82 (15)	C17—C16—N1—C15	−103.4 (2)
C7—C8—C9—C10	−5.7 (2)	C17—C16—N1—C12	82.1 (2)
C2—C1—C10—O2	−4.4 (3)	O3—C15—N2—C11	178.67 (17)
C6—C1—C10—O2	173.79 (18)	N1—C15—N2—C11	−0.75 (19)
C2—C1—C10—C9	176.93 (18)	O3—C15—N2—C19	−7.5 (3)
C6—C1—C10—C9	−4.9 (3)	N1—C15—N2—C19	173.08 (14)
C14—C9—C10—O2	6.9 (3)	C8—C11—N2—C15	−178.39 (18)
C8—C9—C10—O2	−173.18 (17)	C12—C11—N2—C15	0.35 (18)
C14—C9—C10—C1	−174.42 (16)	C8—C11—N2—C19	9.2 (3)
C8—C9—C10—C1	5.5 (3)	C12—C11—N2—C19	−172.03 (16)
C9—C8—C11—N2	−179.39 (17)	C20—C19—N2—C15	−105.30 (18)
C7—C8—C11—N2	4.3 (3)	C20—C19—N2—C11	66.7 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18···O2i	0.93	2.31	3.165 (3)	152
C21—H21···O1ii	0.93	2.38	3.275 (3)	161
C2—H2···O3iii	0.93	2.62	3.333 (3)	134

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C18—H18⋯O2i	0.93	2.31	3.165 (3)	152
C21—H21⋯O1ii	0.93	2.38	3.275 (3)	161
C2—H2⋯O3iii	0.93	2.62	3.333 (3)	134

Symmetry codes: (i) ; (ii) ; (iii) .