Diethyl 2,6,11-trioxo-2,3-dihydro-1H-anthra[1,2-d]imidazole-1,3-diacetate.

The title compound, C(23)H(20)N(2)O(7), consists of three fused six-membered rings (A, B and C) and one five-membered ring (D), linked to two ethyl acetate groups. The four fused rings are slightly folded around the O=C⋯C=O direction of the anthraquinone system, with a dihedral angle of 3.07 (8)° between the fused five- and six-membered rings (C and D) and the terminal ring (A). The planes through the atoms forming each acetate group are nearly perpendicular to the mean plane of the anthra[1,2-d]imidazole system, as indicated by the dihedral angles between them of 79.94 (9) and 85.90 (9)°. The crystal packing displays non-classical C-H⋯O hydrogen bonds.

Related literature

For the biological activity of anthraquinone derivatives, see: Afrakssou et al. (2011 ▶); Guimarães et al. (2009 ▶); Zoń et al. (2003 ▶). For their applications as colourants, see: Mori et al. (1990 ▶); Kowalczyk et al. (2010 ▶); Ossowski et al. (2005 ▶).

Experimental

Crystal data

C23H20N2O7

M = 436.41

Monoclinic,

a = 17.462 (1) Å

b = 13.0646 (9) Å

c = 9.1411 (6) Å

β = 103.915 (3)°

V = 2024.2 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 100 K

0.49 × 0.11 × 0.09 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2008a ▶) T min = 0.602, T max = 0.746

32055 measured reflections

5006 independent reflections

3339 reflections with I > 2σ(I)

R int = 0.057

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.153

S = 1.01

5006 reflections

291 parameters

H-atom parameters constrained

Δρmax = 0.57 e Å−3

Δρmin = −0.32 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, 2008b ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008b ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and ORTEPIII (Burnett & Johnson, 1996 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811028091/bt5578sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811028091/bt5578Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811028091/bt5578Isup3.cml

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

C23H20N2O7	F(000) = 912
Mr = 436.41	Dx = 1.432 Mg m−3
Monoclinic, P21/c	Melting point: 443 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 17.462 (1) Å	Cell parameters from 5953 reflections
b = 13.0646 (9) Å	θ = 2.8–28.2°
c = 9.1411 (6) Å	µ = 0.11 mm−1
β = 103.915 (3)°	T = 100 K
V = 2024.2 (2) Å3	Needle, orange
Z = 4	0.49 × 0.11 × 0.09 mm

Bruker APEXII CCD diffractometer	5006 independent reflections
Radiation source: fine-focus sealed tube	3339 reflections with I > 2σ(I)
graphite	Rint = 0.057
φ and ω scans	θmax = 28.3°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 2008a)	h = −23→17
Tmin = 0.602, Tmax = 0.746	k = −17→17
32055 measured reflections	l = −12→12

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.153	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0807P)2 + 0.7872P] where P = (Fo2 + 2Fc2)/3
5006 reflections	(Δ/σ)max < 0.001
291 parameters	Δρmax = 0.57 e Å−3
0 restraints	Δρmin = −0.32 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'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	0.03454 (11)	0.81216 (15)	0.1634 (2)	0.0212 (4)
C2	−0.01666 (12)	0.88216 (16)	0.0739 (2)	0.0251 (4)
H2	−0.0120	0.9531	0.0970	0.030*
C3	−0.07428 (12)	0.84794 (18)	−0.0487 (2)	0.0291 (5)
H3	−0.1089	0.8956	−0.1099	0.035*
C4	−0.08148 (12)	0.74399 (17)	−0.0823 (2)	0.0300 (5)
H4	−0.1204	0.7211	−0.1674	0.036*
C5	−0.03235 (11)	0.67372 (16)	0.0073 (2)	0.0251 (4)
H5	−0.0378	0.6027	−0.0153	0.030*
C6	0.02552 (11)	0.70791 (15)	0.1315 (2)	0.0213 (4)
C7	0.07787 (11)	0.63253 (15)	0.2280 (2)	0.0211 (4)
C8	0.13726 (11)	0.67067 (15)	0.3619 (2)	0.0195 (4)
C9	0.14819 (11)	0.77711 (14)	0.3921 (2)	0.0180 (4)
C10	0.09975 (11)	0.85232 (15)	0.2866 (2)	0.0207 (4)
C11	0.18249 (11)	0.59666 (14)	0.4533 (2)	0.0208 (4)
H11	0.1729	0.5263	0.4296	0.025*
C12	0.24099 (11)	0.62368 (15)	0.5779 (2)	0.0213 (4)
H12	0.2722	0.5733	0.6399	0.026*
C13	0.25240 (11)	0.72640 (15)	0.6087 (2)	0.0196 (4)
C14	0.20748 (11)	0.80493 (14)	0.5205 (2)	0.0184 (4)
C15	0.29890 (11)	0.87703 (15)	0.7166 (2)	0.0219 (4)
C16	0.36449 (12)	0.71882 (15)	0.8400 (2)	0.0229 (4)
H16A	0.3382	0.6635	0.8836	0.028*
H16B	0.3880	0.7670	0.9221	0.028*
C17	0.42943 (11)	0.67314 (16)	0.7757 (2)	0.0229 (4)
C18	0.51981 (13)	0.53472 (18)	0.8019 (3)	0.0358 (5)
H18A	0.5572	0.4993	0.8851	0.043*
H18B	0.5506	0.5789	0.7491	0.043*
C19	0.47416 (16)	0.4572 (2)	0.6938 (4)	0.0512 (7)
H19A	0.4439	0.4135	0.7465	0.077*
H19B	0.5109	0.4149	0.6539	0.077*
H19C	0.4380	0.4926	0.6105	0.077*
C20	0.21415 (12)	1.00388 (15)	0.5665 (2)	0.0238 (4)
H20A	0.2225	1.0390	0.6651	0.029*
H20B	0.1573	1.0081	0.5163	0.029*
C21	0.26099 (12)	1.05796 (16)	0.4711 (2)	0.0250 (4)
C22	0.29699 (17)	1.22304 (19)	0.4012 (3)	0.0454 (6)
H22A	0.2759	1.2132	0.2915	0.054*
H22B	0.3536	1.2046	0.4272	0.054*
C23	0.2867 (2)	1.3309 (2)	0.4429 (3)	0.0564 (8)
H23A	0.2304	1.3476	0.4199	0.085*
H23B	0.3135	1.3761	0.3855	0.085*
H23C	0.3096	1.3403	0.5510	0.085*
N1	0.30651 (9)	0.77227 (12)	0.72586 (17)	0.0199 (3)
N2	0.23663 (9)	0.89680 (12)	0.59127 (18)	0.0203 (3)
O1	0.07231 (9)	0.54083 (10)	0.19817 (16)	0.0272 (3)
O2	0.11351 (9)	0.94387 (11)	0.29568 (17)	0.0309 (4)
O3	0.33699 (8)	0.94101 (11)	0.80032 (15)	0.0260 (3)
O4	0.44572 (9)	0.70173 (12)	0.66182 (16)	0.0325 (4)
O5	0.46530 (9)	0.59785 (12)	0.86323 (17)	0.0336 (4)
O6	0.29952 (9)	1.01755 (12)	0.39486 (17)	0.0320 (4)
O7	0.25385 (10)	1.15896 (12)	0.48532 (19)	0.0374 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0234 (9)	0.0248 (10)	0.0172 (9)	−0.0005 (8)	0.0085 (7)	−0.0014 (7)
C2	0.0291 (10)	0.0255 (10)	0.0215 (10)	0.0010 (8)	0.0077 (8)	0.0019 (8)
C3	0.0274 (10)	0.0357 (12)	0.0234 (10)	0.0036 (9)	0.0044 (8)	0.0035 (9)
C4	0.0267 (10)	0.0387 (13)	0.0230 (10)	−0.0040 (9)	0.0030 (8)	−0.0016 (9)
C5	0.0251 (10)	0.0264 (11)	0.0252 (10)	−0.0045 (8)	0.0087 (8)	−0.0055 (8)
C6	0.0210 (9)	0.0261 (10)	0.0194 (9)	−0.0022 (8)	0.0097 (7)	−0.0007 (7)
C7	0.0241 (9)	0.0228 (10)	0.0193 (9)	−0.0035 (8)	0.0111 (8)	−0.0016 (7)
C8	0.0228 (9)	0.0199 (10)	0.0184 (9)	−0.0014 (7)	0.0099 (7)	−0.0012 (7)
C9	0.0203 (9)	0.0190 (9)	0.0167 (9)	0.0016 (7)	0.0084 (7)	0.0005 (7)
C10	0.0239 (9)	0.0214 (10)	0.0181 (9)	0.0005 (8)	0.0080 (7)	0.0001 (7)
C11	0.0278 (10)	0.0149 (9)	0.0216 (9)	−0.0014 (8)	0.0097 (8)	−0.0012 (7)
C12	0.0260 (10)	0.0210 (10)	0.0187 (9)	0.0026 (8)	0.0088 (8)	0.0033 (7)
C13	0.0207 (9)	0.0228 (10)	0.0170 (9)	0.0007 (7)	0.0078 (7)	0.0008 (7)
C14	0.0212 (9)	0.0168 (9)	0.0198 (9)	−0.0007 (7)	0.0099 (7)	−0.0004 (7)
C15	0.0229 (9)	0.0243 (10)	0.0207 (9)	0.0008 (8)	0.0096 (8)	0.0001 (8)
C16	0.0269 (10)	0.0257 (10)	0.0161 (9)	0.0015 (8)	0.0050 (8)	0.0018 (8)
C17	0.0216 (9)	0.0281 (11)	0.0178 (9)	0.0002 (8)	0.0023 (7)	0.0024 (8)
C18	0.0273 (11)	0.0401 (14)	0.0414 (13)	0.0138 (10)	0.0107 (10)	0.0111 (10)
C19	0.0367 (14)	0.0409 (16)	0.078 (2)	0.0058 (11)	0.0164 (14)	−0.0043 (14)
C20	0.0282 (10)	0.0188 (10)	0.0249 (10)	0.0003 (8)	0.0077 (8)	−0.0028 (8)
C21	0.0260 (10)	0.0241 (10)	0.0249 (10)	−0.0004 (8)	0.0063 (8)	−0.0003 (8)
C22	0.0604 (16)	0.0309 (13)	0.0533 (16)	−0.0024 (12)	0.0305 (13)	0.0111 (11)
C23	0.082 (2)	0.0395 (16)	0.0500 (17)	−0.0095 (15)	0.0199 (15)	0.0078 (13)
N1	0.0225 (8)	0.0196 (8)	0.0174 (8)	0.0010 (6)	0.0047 (6)	−0.0013 (6)
N2	0.0234 (8)	0.0179 (8)	0.0202 (8)	−0.0005 (6)	0.0062 (6)	−0.0014 (6)
O1	0.0325 (8)	0.0224 (8)	0.0270 (7)	−0.0027 (6)	0.0078 (6)	−0.0044 (6)
O2	0.0374 (8)	0.0211 (8)	0.0301 (8)	−0.0007 (6)	0.0000 (6)	0.0032 (6)
O3	0.0281 (7)	0.0247 (8)	0.0253 (7)	−0.0037 (6)	0.0067 (6)	−0.0054 (6)
O4	0.0330 (8)	0.0458 (10)	0.0213 (7)	0.0098 (7)	0.0116 (6)	0.0105 (6)
O5	0.0315 (8)	0.0438 (10)	0.0276 (8)	0.0139 (7)	0.0114 (6)	0.0144 (7)
O6	0.0389 (9)	0.0311 (8)	0.0304 (8)	−0.0011 (7)	0.0167 (7)	−0.0025 (6)
O7	0.0519 (10)	0.0224 (8)	0.0454 (10)	−0.0007 (7)	0.0261 (8)	0.0036 (7)

C1—C6	1.394 (3)	C15—N2	1.401 (2)
C1—C2	1.397 (3)	C16—N1	1.447 (2)
C1—C10	1.492 (3)	C16—C17	1.519 (3)
C2—C3	1.388 (3)	C16—H16A	0.9900
C2—H2	0.9500	C16—H16B	0.9900
C3—C4	1.391 (3)	C17—O4	1.203 (2)
C3—H3	0.9500	C17—O5	1.326 (2)
C4—C5	1.383 (3)	C18—O5	1.469 (3)
C4—H4	0.9500	C18—C19	1.503 (4)
C5—C6	1.399 (3)	C18—H18A	0.9900
C5—H5	0.9500	C18—H18B	0.9900
C6—C7	1.482 (3)	C19—H19A	0.9800
C7—O1	1.227 (2)	C19—H19B	0.9800
C7—C8	1.487 (3)	C19—H19C	0.9800
C8—C11	1.393 (3)	C20—N2	1.456 (2)
C8—C9	1.422 (3)	C20—C21	1.508 (3)
C9—C14	1.413 (3)	C20—H20A	0.9900
C9—C10	1.489 (3)	C20—H20B	0.9900
C10—O2	1.219 (2)	C21—O6	1.201 (2)
C11—C12	1.380 (3)	C21—O7	1.335 (3)
C11—H11	0.9500	C22—O7	1.462 (3)
C12—C13	1.376 (3)	C22—C23	1.482 (4)
C12—H12	0.9500	C22—H22A	0.9900
C13—N1	1.383 (2)	C22—H22B	0.9900
C13—C14	1.419 (3)	C23—H23A	0.9800
C14—N2	1.400 (2)	C23—H23B	0.9800
C15—O3	1.217 (2)	C23—H23C	0.9800
C15—N1	1.376 (2)
C6—C1—C2	119.54 (18)	N1—C16—H16B	109.3
C6—C1—C10	121.94 (17)	C17—C16—H16B	109.3
C2—C1—C10	118.47 (18)	H16A—C16—H16B	108.0
C3—C2—C1	119.95 (19)	O4—C17—O5	125.21 (19)
C3—C2—H2	120.0	O4—C17—C16	124.53 (18)
C1—C2—H2	120.0	O5—C17—C16	110.26 (16)
C2—C3—C4	120.1 (2)	O5—C18—C19	109.85 (19)
C2—C3—H3	119.9	O5—C18—H18A	109.7
C4—C3—H3	119.9	C19—C18—H18A	109.7
C5—C4—C3	120.47 (19)	O5—C18—H18B	109.7
C5—C4—H4	119.8	C19—C18—H18B	109.7
C3—C4—H4	119.8	H18A—C18—H18B	108.2
C4—C5—C6	119.52 (19)	C18—C19—H19A	109.5
C4—C5—H5	120.2	C18—C19—H19B	109.5
C6—C5—H5	120.2	H19A—C19—H19B	109.5
C1—C6—C5	120.32 (18)	C18—C19—H19C	109.5
C1—C6—C7	120.17 (17)	H19A—C19—H19C	109.5
C5—C6—C7	119.51 (18)	H19B—C19—H19C	109.5
O1—C7—C6	120.79 (17)	N2—C20—C21	112.12 (16)
O1—C7—C8	120.81 (18)	N2—C20—H20A	109.2
C6—C7—C8	118.40 (17)	C21—C20—H20A	109.2
C11—C8—C9	122.16 (17)	N2—C20—H20B	109.2
C11—C8—C7	116.35 (17)	C21—C20—H20B	109.2
C9—C8—C7	121.47 (17)	H20A—C20—H20B	107.9
C14—C9—C8	116.75 (16)	O6—C21—O7	124.74 (19)
C14—C9—C10	123.82 (17)	O6—C21—C20	125.98 (19)
C8—C9—C10	119.39 (16)	O7—C21—C20	109.28 (16)
O2—C10—C9	122.11 (17)	O7—C22—C23	107.4 (2)
O2—C10—C1	119.91 (17)	O7—C22—H22A	110.2
C9—C10—C1	117.94 (16)	C23—C22—H22A	110.2
C12—C11—C8	121.18 (18)	O7—C22—H22B	110.2
C12—C11—H11	119.4	C23—C22—H22B	110.2
C8—C11—H11	119.4	H22A—C22—H22B	108.5
C13—C12—C11	117.42 (17)	C22—C23—H23A	109.5
C13—C12—H12	121.3	C22—C23—H23B	109.5
C11—C12—H12	121.3	H23A—C23—H23B	109.5
C12—C13—N1	128.30 (17)	C22—C23—H23C	109.5
C12—C13—C14	123.76 (17)	H23A—C23—H23C	109.5
N1—C13—C14	107.94 (16)	H23B—C23—H23C	109.5
N2—C14—C9	135.76 (17)	C15—N1—C13	110.22 (15)
N2—C14—C13	105.53 (16)	C15—N1—C16	124.39 (16)
C9—C14—C13	118.71 (17)	C13—N1—C16	125.37 (16)
O3—C15—N1	127.91 (18)	C14—N2—C15	110.13 (15)
O3—C15—N2	125.93 (18)	C14—N2—C20	134.24 (16)
N1—C15—N2	106.15 (16)	C15—N2—C20	115.56 (16)
N1—C16—C17	111.62 (15)	C17—O5—C18	116.20 (16)
N1—C16—H16A	109.3	C21—O7—C22	116.27 (17)
C17—C16—H16A	109.3
C6—C1—C2—C3	−2.2 (3)	C10—C9—C14—N2	3.2 (3)
C10—C1—C2—C3	175.18 (18)	C8—C9—C14—C13	0.8 (2)
C1—C2—C3—C4	0.4 (3)	C10—C9—C14—C13	−177.01 (17)
C2—C3—C4—C5	1.1 (3)	C12—C13—C14—N2	178.95 (17)
C3—C4—C5—C6	−0.7 (3)	N1—C13—C14—N2	−0.7 (2)
C2—C1—C6—C5	2.5 (3)	C12—C13—C14—C9	−0.9 (3)
C10—C1—C6—C5	−174.73 (17)	N1—C13—C14—C9	179.43 (16)
C2—C1—C6—C7	−178.23 (17)	N1—C16—C17—O4	21.5 (3)
C10—C1—C6—C7	4.5 (3)	N1—C16—C17—O5	−158.68 (16)
C4—C5—C6—C1	−1.1 (3)	N2—C20—C21—O6	15.8 (3)
C4—C5—C6—C7	179.67 (18)	N2—C20—C21—O7	−163.51 (17)
C1—C6—C7—O1	−177.49 (17)	O3—C15—N1—C13	−179.68 (19)
C5—C6—C7—O1	1.8 (3)	N2—C15—N1—C13	1.4 (2)
C1—C6—C7—C8	2.6 (3)	O3—C15—N1—C16	−1.2 (3)
C5—C6—C7—C8	−178.19 (17)	N2—C15—N1—C16	179.85 (16)
O1—C7—C8—C11	−3.0 (3)	C12—C13—N1—C15	179.94 (18)
C6—C7—C8—C11	176.95 (16)	C14—C13—N1—C15	−0.4 (2)
O1—C7—C8—C9	175.54 (17)	C12—C13—N1—C16	1.5 (3)
C6—C7—C8—C9	−4.5 (3)	C14—C13—N1—C16	−178.88 (16)
C11—C8—C9—C14	−0.1 (3)	C17—C16—N1—C15	−107.4 (2)
C7—C8—C9—C14	−178.58 (16)	C17—C16—N1—C13	70.9 (2)
C11—C8—C9—C10	177.81 (17)	C9—C14—N2—C15	−178.6 (2)
C7—C8—C9—C10	−0.6 (3)	C13—C14—N2—C15	1.6 (2)
C14—C9—C10—O2	7.6 (3)	C9—C14—N2—C20	4.7 (4)
C8—C9—C10—O2	−170.20 (18)	C13—C14—N2—C20	−175.14 (19)
C14—C9—C10—C1	−174.76 (16)	O3—C15—N2—C14	179.19 (18)
C8—C9—C10—C1	7.5 (3)	N1—C15—N2—C14	−1.8 (2)
C6—C1—C10—O2	168.12 (18)	O3—C15—N2—C20	−3.4 (3)
C2—C1—C10—O2	−9.2 (3)	N1—C15—N2—C20	175.55 (15)
C6—C1—C10—C9	−9.6 (3)	C21—C20—N2—C14	−95.1 (2)
C2—C1—C10—C9	173.13 (17)	C21—C20—N2—C15	88.3 (2)
C9—C8—C11—C12	−0.6 (3)	O4—C17—O5—C18	−10.5 (3)
C7—C8—C11—C12	177.95 (17)	C16—C17—O5—C18	169.61 (17)
C8—C11—C12—C13	0.5 (3)	C19—C18—O5—C17	−80.1 (2)
C11—C12—C13—N1	179.80 (18)	O6—C21—O7—C22	−0.2 (3)
C11—C12—C13—C14	0.2 (3)	C20—C21—O7—C22	179.08 (19)
C8—C9—C14—N2	−178.98 (19)	C23—C22—O7—C21	−175.2 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O1i	0.95	2.49	3.353 (2)	151.
C12—H12···O6ii	0.95	2.56	3.380 (2)	145.
C16—H16A···O6ii	0.99	2.47	3.369 (3)	151.
C16—H16B···O4ii	0.99	2.22	3.120 (2)	151.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O1i	0.95	2.49	3.353 (2)	151
C12—H12⋯O6ii	0.95	2.56	3.380 (2)	145
C16—H16A⋯O6ii	0.99	2.47	3.369 (3)	151
C16—H16B⋯O4ii	0.99	2.22	3.120 (2)	151

Symmetry codes: (i) ; (ii) .