Di-tert-butyl 2,6,11-trioxo-2,3-dihydro-1H-anthra[1,2-d]imidazole-1,3-diacetate

Afrakssou, Z.; Rodi, Y.K.; Saffon, N.; Essassi, E.M.; Ng, S.W.

doi:10.1107/S1600536811022914

organic compounds

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ISSN: 2056-9890

Volume 67| Part 7| July 2011| Page o1730

doi:10.1107/S1600536811022914

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Di-tert-butyl 2,6,11-trioxo-2,3-dihydro-1H-anthra[1,2-d]imidazole-1,3-diacetate

Zahra Afrakssou,^a Yousef Kandri Rodi,^a Natalie Saffon,^b El Mokhtar Essassi ^c and Seik Weng Ng ^d ^*

^aLaboratoire de Chimie Organique Appliquée, Faculté des Sciences et Techniques, Université Sidi Mohamed Ben Abdallah, Fés, Morocco, ^bService Commun Rayons-X FR2599, Université Paul Sabatier Bâtiment 2R1, 118 route de Narbonne, Toulouse, France, ^cLaboratoire de Chimie Organique Hétérocyclique, Pôle de Compétences Pharmacochimie, Université Mohammed V-Agdal, BP 1014 Avenue Ibn Batout, Rabat, Morocco, and ^dDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 12 June 2011; accepted 13 June 2011; online 18 June 2011)

The fused-ring system of the title compound, C₂₇H₂₈N₂O₇, which comprises one five- and three six-membered rings, is approximately planar (r.m.s. deviation = 0.133 Å), the system being buckled along the axis passing through the O atoms of the anthraquinone portion of the molecule. Within the anthraquinone portion, the two benzene rings are aligned at 7.3 (2)°. In the crystal, one of the tert-butyl groups is disordered over two sets of sites in a 1:1 ratio. Weak intermolecular C—H⋯O hydrogen bonding is present in the crystal structure.

Related literature

For a related structure, see: Afrakssou et al. (2010 ).

Experimental

Crystal data

C₂₇H₂₈N₂O₇
M_r = 492.51
Monoclinic, P 2₁ /c
a = 19.5785 (4) Å
b = 13.0330 (3) Å
c = 9.9269 (2) Å
β = 90.583 (1)°
V = 2532.88 (9) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.50 × 0.10 × 0.10 mm

Data collection

Bruker APEXII diffractometer
37371 measured reflections
5172 independent reflections
2929 reflections with I > 2σ(I)
R_int = 0.070

Refinement

R[F² > 2σ(F²)] = 0.056
wR(F²) = 0.190
S = 1.04
5172 reflections
353 parameters
48 restraints
H-atom parameters constrained
Δρ_max = 0.51 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C16—H16B⋯O2ⁱ	0.97	2.54	3.320 (4)	137
C22—H22A⋯O5ⁱ	0.97	2.47	3.391 (3)	159
C22—H22B⋯O7ⁱ	0.97	2.29	3.190 (4)	154
Symmetry code: (i) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2005 ); cell refinement: SAINT (Bruker, 2005); 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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811022914/xu5244sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811022914/xu5244Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811022914/xu5244Isup3.cml

checkCIF report

Comment top

A recent study reported 1,3-diallyl-1H-anthra[1,2-d]imidazole-2,6,11(3H)-trione (Afrakssou et al., 2010). The title compound has in place of the allyl group the tert-butyl acetate ester group. The fused-ring system of C₂₇H₂₈N₂O₇ (Scheme I) that comprises one five-membered ring and three six-membered rings is appromimately planar, the system being buckled along the axis passing through the O atoms of the anthraquinone portion of the molecule. With the anthraquinone portion, the two benzene rings are aligned at 7.3 (2) ° (Fig. 1).

Related literature top

For a related structure, see: Afrakssou et al. (2010).

Experimental top

To a solution of 1H-anthra [2,1-d] imidazole-2, 6,11(3H)-trione (0.3 g, 1.13 mmol), potassium carbonate (0.62 g, 4.53 mmol) and tetra n-butyl ammonium bromide (0.03 g, 0.018 mmol) in DMF (15 ml) was added tert-butyl bromoacetate (0.56 ml, 0.47 mmol). Stirring was continued at room temperature for 24 h. The mixture was filtered and the solvent removed. The residue was extracted with water. The organic compound was chromatographed on a column of silica gel with ethyl acetate/hexane. Orange prismatic crystals were isolated when the solvent was allowed to evaporate.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); 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).

Figures top

Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of C₂₇H₂₈N₂O₇ at the 50% probability level; hydrogen atoms are drawn as arbitrary radius. The disorder is not shown.

Di-tert-butyl 2,6,11-trioxo-2,3-dihydro-1H-anthra[1,2-d]imidazole-1,3-diacetate top

Crystal data top

C₂₇H₂₈N₂O₇	F(000) = 1040
M_r = 492.51	D_x = 1.292 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5392 reflections
a = 19.5785 (4) Å	θ = 2.6–23.5°
b = 13.0330 (3) Å	µ = 0.09 mm⁻¹
c = 9.9269 (2) Å	T = 293 K
β = 90.583 (1)°	Prism, orange
V = 2532.88 (9) Å³	0.50 × 0.10 × 0.10 mm
Z = 4

Data collection top

Bruker APEXII diffractometer	2929 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.070
Graphite monochromator	θ_max = 26.4°, θ_min = 1.9°
ϕ and ω scans	h = −24→24
37371 measured reflections	k = −16→16
5172 independent reflections	l = −12→12

Refinement top

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)] = 0.056	H-atom parameters constrained
wR(F²) = 0.190	w = 1/[σ²(F_o²) + (0.086P)² + 1.5472P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max = 0.001
5172 reflections	Δρ_max = 0.51 e Å⁻³
353 parameters	Δρ_min = −0.31 e Å⁻³
48 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: 0.0068 (12)

Crystal data top

C₂₇H₂₈N₂O₇	V = 2532.88 (9) Å³
M_r = 492.51	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 19.5785 (4) Å	µ = 0.09 mm⁻¹
b = 13.0330 (3) Å	T = 293 K
c = 9.9269 (2) Å	0.50 × 0.10 × 0.10 mm
β = 90.583 (1)°

Data collection top

Bruker APEXII diffractometer	2929 reflections with I > 2σ(I)
37371 measured reflections	R_int = 0.070
5172 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.056	48 restraints
wR(F²) = 0.190	H-atom parameters constrained
S = 1.04	Δρ_max = 0.51 e Å⁻³
5172 reflections	Δρ_min = −0.31 e Å⁻³
353 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1	0.11503 (11)	0.55465 (16)	0.3982 (2)	0.0529 (6)
O2	0.09491 (12)	0.94796 (16)	0.5443 (2)	0.0529 (6)
O3	0.33296 (11)	0.57044 (16)	0.0875 (2)	0.0468 (6)
O4	0.21612 (11)	0.36402 (15)	0.3971 (2)	0.0435 (5)
O5	0.26519 (12)	0.50970 (17)	0.4779 (2)	0.0504 (6)
O6	0.46459 (11)	0.8677 (2)	0.1416 (2)	0.0636 (7)
O7	0.41731 (15)	0.7703 (3)	0.3008 (3)	0.1046 (13)
N1	0.24308 (12)	0.60746 (17)	0.2331 (2)	0.0347 (6)
N2	0.30396 (12)	0.73659 (18)	0.1509 (2)	0.0365 (6)
C1	0.11879 (14)	0.6422 (2)	0.4430 (3)	0.0368 (7)
C2	0.07265 (14)	0.6734 (2)	0.5542 (3)	0.0358 (7)
C3	0.03615 (15)	0.5987 (3)	0.6220 (3)	0.0452 (8)
H3	0.0414	0.5302	0.5985	0.054*
C4	−0.00819 (16)	0.6249 (3)	0.7246 (3)	0.0484 (8)
H4	−0.0315	0.5743	0.7714	0.058*
C5	−0.01722 (16)	0.7274 (3)	0.7564 (3)	0.0484 (8)
H5	−0.0471	0.7455	0.8247	0.058*
C6	0.01780 (15)	0.8034 (3)	0.6876 (3)	0.0450 (8)
H6	0.0106	0.8721	0.7084	0.054*
C7	0.06374 (14)	0.7765 (2)	0.5873 (3)	0.0357 (7)
C8	0.10414 (14)	0.8571 (2)	0.5187 (3)	0.0381 (7)
C9	0.15721 (14)	0.8242 (2)	0.4211 (3)	0.0336 (6)
C10	0.19751 (15)	0.9009 (2)	0.3665 (3)	0.0392 (7)
H10	0.1901	0.9687	0.3917	0.047*
C11	0.24838 (15)	0.8789 (2)	0.2757 (3)	0.0402 (7)
H11	0.2757	0.9304	0.2403	0.048*
C12	0.25714 (14)	0.7778 (2)	0.2397 (3)	0.0335 (6)
C13	0.21739 (13)	0.6969 (2)	0.2917 (3)	0.0307 (6)
C14	0.16564 (13)	0.7197 (2)	0.3849 (3)	0.0320 (6)
C15	0.29788 (15)	0.6315 (2)	0.1490 (3)	0.0377 (7)
C16	0.22597 (15)	0.4999 (2)	0.2478 (3)	0.0357 (7)
H16A	0.2529	0.4600	0.1852	0.043*
H16B	0.1782	0.4901	0.2246	0.043*
C17	0.23880 (15)	0.4609 (2)	0.3887 (3)	0.0384 (7)
C18	0.21185 (18)	0.3115 (3)	0.5299 (3)	0.0516 (9)
C19	0.2819 (2)	0.2970 (4)	0.5889 (5)	0.0877 (15)
H19A	0.3091	0.2572	0.5283	0.132*
H19B	0.2786	0.2618	0.6736	0.132*
H19C	0.3029	0.3628	0.6028	0.132*
C20	0.1781 (2)	0.2106 (3)	0.4936 (4)	0.0653 (11)
H20A	0.2081	0.1713	0.4377	0.098*
H20B	0.1361	0.2237	0.4458	0.098*
H20C	0.1687	0.1729	0.5744	0.098*
C21	0.1649 (2)	0.3734 (3)	0.6196 (4)	0.0678 (11)
H21A	0.1866	0.4371	0.6431	0.102*
H21B	0.1555	0.3352	0.7000	0.102*
H21C	0.1228	0.3871	0.5723	0.102*
C22	0.36054 (14)	0.7901 (2)	0.0903 (3)	0.0392 (7)
H22A	0.3449	0.8556	0.0554	0.047*
H22B	0.3778	0.7502	0.0157	0.047*
C23	0.41684 (16)	0.8075 (3)	0.1919 (3)	0.0500 (8)
C24	0.5229 (2)	0.9059 (4)	0.2242 (5)	0.0988 (18)
C25	0.4904 (6)	0.9979 (8)	0.3039 (11)	0.111 (4)	0.50
H25A	0.4702	1.0455	0.2415	0.166*	0.50
H25B	0.5253	1.0319	0.3558	0.166*	0.50
H25C	0.4559	0.9722	0.3631	0.166*	0.50
C26	0.5707 (6)	0.9463 (9)	0.1166 (11)	0.088 (4)	0.50
H26A	0.5858	0.8905	0.0615	0.132*	0.50
H26B	0.6094	0.9785	0.1589	0.132*	0.50
H26C	0.5469	0.9956	0.0616	0.132*	0.50
C27	0.5567 (6)	0.8344 (8)	0.3191 (11)	0.113 (4)	0.50
H27A	0.5805	0.7825	0.2695	0.170*	0.50
H27B	0.5229	0.8026	0.3748	0.170*	0.50
H27C	0.5886	0.8715	0.3747	0.170*	0.50
C25'	0.5058 (7)	0.9391 (11)	0.3628 (9)	0.138 (5)	0.50
H25D	0.4839	0.8838	0.4093	0.207*	0.50
H25E	0.4757	0.9971	0.3586	0.207*	0.50
H25F	0.5469	0.9579	0.4102	0.207*	0.50
C26'	0.5574 (8)	0.9876 (8)	0.1401 (13)	0.102 (5)	0.50
H26D	0.5656	0.9613	0.0514	0.153*	0.50
H26E	0.6001	1.0064	0.1817	0.153*	0.50
H26F	0.5284	1.0469	0.1339	0.153*	0.50
C27'	0.5644 (6)	0.8040 (7)	0.2276 (13)	0.125 (4)	0.50
H27D	0.5753	0.7840	0.1373	0.187*	0.50
H27E	0.5376	0.7513	0.2692	0.187*	0.50
H27F	0.6058	0.8141	0.2785	0.187*	0.50

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0527 (14)	0.0363 (13)	0.0702 (16)	−0.0088 (10)	0.0218 (12)	−0.0110 (11)
O2	0.0533 (14)	0.0369 (13)	0.0689 (16)	0.0024 (10)	0.0138 (12)	−0.0128 (11)
O3	0.0468 (13)	0.0471 (13)	0.0468 (13)	0.0058 (10)	0.0136 (10)	−0.0021 (10)
O4	0.0575 (13)	0.0329 (11)	0.0400 (12)	−0.0022 (10)	0.0018 (10)	0.0040 (9)
O5	0.0556 (14)	0.0515 (14)	0.0441 (13)	−0.0146 (11)	−0.0043 (10)	−0.0006 (10)
O6	0.0410 (13)	0.095 (2)	0.0546 (15)	−0.0213 (13)	−0.0013 (11)	0.0134 (13)
O7	0.0606 (18)	0.197 (4)	0.0563 (18)	−0.043 (2)	−0.0125 (14)	0.055 (2)
N1	0.0357 (13)	0.0299 (12)	0.0385 (13)	−0.0027 (10)	0.0071 (10)	−0.0007 (10)
N2	0.0335 (13)	0.0361 (14)	0.0402 (14)	−0.0039 (10)	0.0071 (11)	0.0026 (10)
C1	0.0338 (15)	0.0302 (16)	0.0465 (17)	−0.0005 (12)	0.0034 (13)	−0.0010 (12)
C2	0.0269 (14)	0.0401 (16)	0.0404 (16)	−0.0015 (12)	0.0031 (12)	0.0001 (12)
C3	0.0384 (17)	0.0448 (18)	0.0526 (19)	−0.0030 (14)	0.0082 (14)	−0.0007 (14)
C4	0.0379 (17)	0.059 (2)	0.0490 (19)	−0.0024 (15)	0.0099 (15)	0.0031 (15)
C5	0.0353 (17)	0.062 (2)	0.0476 (19)	0.0006 (15)	0.0093 (14)	−0.0059 (16)
C6	0.0371 (17)	0.0472 (19)	0.0510 (19)	0.0030 (14)	0.0056 (14)	−0.0123 (15)
C7	0.0283 (15)	0.0378 (16)	0.0408 (16)	0.0007 (12)	0.0013 (12)	−0.0045 (12)
C8	0.0332 (15)	0.0371 (17)	0.0439 (17)	0.0015 (13)	−0.0020 (13)	−0.0062 (13)
C9	0.0297 (14)	0.0293 (15)	0.0417 (16)	−0.0003 (11)	−0.0014 (12)	−0.0023 (12)
C10	0.0399 (16)	0.0287 (15)	0.0489 (18)	−0.0008 (12)	0.0012 (14)	−0.0009 (12)
C11	0.0394 (16)	0.0329 (16)	0.0483 (18)	−0.0050 (13)	0.0043 (13)	0.0045 (13)
C12	0.0295 (14)	0.0347 (15)	0.0363 (15)	0.0004 (12)	0.0014 (12)	0.0012 (12)
C13	0.0287 (14)	0.0285 (14)	0.0348 (14)	−0.0002 (11)	−0.0012 (11)	−0.0012 (11)
C14	0.0282 (14)	0.0313 (15)	0.0366 (15)	−0.0011 (11)	0.0014 (11)	−0.0010 (11)
C15	0.0349 (15)	0.0402 (17)	0.0381 (16)	0.0004 (13)	0.0035 (13)	0.0017 (13)
C16	0.0419 (16)	0.0272 (14)	0.0382 (16)	0.0013 (12)	0.0048 (12)	−0.0029 (11)
C17	0.0384 (16)	0.0365 (17)	0.0405 (17)	−0.0022 (13)	0.0025 (13)	0.0001 (13)
C18	0.061 (2)	0.050 (2)	0.0438 (19)	−0.0059 (16)	−0.0049 (16)	0.0148 (15)
C19	0.071 (3)	0.097 (3)	0.095 (3)	−0.001 (2)	−0.019 (2)	0.048 (3)
C20	0.091 (3)	0.042 (2)	0.063 (2)	−0.0064 (19)	0.004 (2)	0.0163 (17)
C21	0.090 (3)	0.063 (2)	0.051 (2)	−0.023 (2)	0.018 (2)	−0.0003 (18)
C22	0.0337 (15)	0.0465 (18)	0.0377 (16)	−0.0033 (13)	0.0070 (13)	0.0050 (13)
C23	0.0335 (17)	0.073 (2)	0.0437 (19)	−0.0046 (16)	0.0079 (14)	0.0119 (16)
C24	0.052 (3)	0.162 (5)	0.082 (3)	−0.047 (3)	−0.014 (2)	0.022 (3)
C25	0.109 (7)	0.121 (8)	0.101 (7)	−0.027 (6)	−0.020 (6)	−0.020 (6)
C26	0.046 (5)	0.121 (8)	0.097 (7)	−0.038 (6)	0.004 (5)	−0.009 (6)
C27	0.082 (6)	0.139 (8)	0.118 (7)	−0.014 (6)	−0.057 (6)	0.018 (6)
C25'	0.135 (8)	0.171 (9)	0.109 (8)	−0.053 (8)	−0.027 (7)	−0.012 (7)
C26'	0.080 (7)	0.125 (9)	0.102 (8)	−0.050 (7)	−0.002 (6)	0.002 (7)
C27'	0.075 (6)	0.186 (9)	0.112 (8)	−0.012 (7)	−0.016 (6)	0.040 (7)

Geometric parameters (Å, º) top

O1—C1	1.227 (3)	C18—C19	1.498 (5)
O2—C8	1.225 (3)	C18—C20	1.512 (5)
O3—C15	1.220 (3)	C18—C21	1.519 (5)
O4—C17	1.341 (3)	C19—H19A	0.9600
O4—C18	1.488 (4)	C19—H19B	0.9600
O5—C17	1.203 (3)	C19—H19C	0.9600
O6—C23	1.322 (4)	C20—H20A	0.9600
O6—C24	1.484 (5)	C20—H20B	0.9600
O7—C23	1.186 (4)	C20—H20C	0.9600
N1—C13	1.399 (3)	C21—H21A	0.9600
N1—C15	1.402 (4)	C21—H21B	0.9600
N1—C16	1.449 (3)	C21—H21C	0.9600
N2—C15	1.374 (4)	C22—C23	1.503 (4)
N2—C12	1.387 (3)	C22—H22A	0.9700
N2—C22	1.445 (4)	C22—H22B	0.9700
C1—C14	1.485 (4)	C24—C27	1.477 (7)
C1—C2	1.490 (4)	C24—C25'	1.484 (7)
C2—C3	1.386 (4)	C24—C26'	1.516 (7)
C2—C7	1.394 (4)	C24—C26	1.521 (7)
C3—C4	1.387 (4)	C24—C27'	1.557 (8)
C3—H3	0.9300	C24—C25	1.574 (7)
C4—C5	1.384 (5)	C25—H25A	0.9600
C4—H4	0.9300	C25—H25B	0.9600
C5—C6	1.389 (4)	C25—H25C	0.9600
C5—H5	0.9300	C26—H26A	0.9600
C6—C7	1.393 (4)	C26—H26B	0.9600
C6—H6	0.9300	C26—H26C	0.9600
C7—C8	1.484 (4)	C27—H27A	0.9600
C8—C9	1.490 (4)	C27—H27B	0.9600
C9—C10	1.387 (4)	C27—H27C	0.9600
C9—C14	1.419 (4)	C25'—H25D	0.9600
C10—C11	1.380 (4)	C25'—H25E	0.9600
C10—H10	0.9300	C25'—H25F	0.9600
C11—C12	1.376 (4)	C26'—H26D	0.9600
C11—H11	0.9300	C26'—H26E	0.9600
C12—C13	1.412 (4)	C26'—H26F	0.9600
C13—C14	1.410 (4)	C27'—H27D	0.9600
C16—C17	1.507 (4)	C27'—H27E	0.9600
C16—H16A	0.9700	C27'—H27F	0.9600
C16—H16B	0.9700

C17—O4—C18	120.7 (2)	H20A—C20—H20B	109.5
C23—O6—C24	122.3 (3)	C18—C20—H20C	109.5
C13—N1—C15	110.0 (2)	H20A—C20—H20C	109.5
C13—N1—C16	132.8 (2)	H20B—C20—H20C	109.5
C15—N1—C16	117.1 (2)	C18—C21—H21A	109.5
C15—N2—C12	109.7 (2)	C18—C21—H21B	109.5
C15—N2—C22	122.8 (2)	H21A—C21—H21B	109.5
C12—N2—C22	126.3 (2)	C18—C21—H21C	109.5
O1—C1—C14	121.8 (3)	H21A—C21—H21C	109.5
O1—C1—C2	119.2 (3)	H21B—C21—H21C	109.5
C14—C1—C2	119.0 (2)	N2—C22—C23	110.7 (2)
C3—C2—C7	119.7 (3)	N2—C22—H22A	109.5
C3—C2—C1	119.2 (3)	C23—C22—H22A	109.5
C7—C2—C1	121.0 (3)	N2—C22—H22B	109.5
C2—C3—C4	120.9 (3)	C23—C22—H22B	109.5
C2—C3—H3	119.6	H22A—C22—H22B	108.1
C4—C3—H3	119.6	O7—C23—O6	126.0 (3)
C5—C4—C3	119.2 (3)	O7—C23—C22	123.3 (3)
C5—C4—H4	120.4	O6—C23—C22	110.7 (3)
C3—C4—H4	120.4	C27—C24—O6	118.5 (5)
C4—C5—C6	120.7 (3)	C27—C24—C25'	72.3 (6)
C4—C5—H5	119.6	O6—C24—C25'	115.5 (6)
C6—C5—H5	119.6	C27—C24—C26'	126.5 (9)
C5—C6—C7	119.8 (3)	O6—C24—C26'	106.0 (7)
C5—C6—H6	120.1	C25'—C24—C26'	114.3 (7)
C7—C6—H6	120.1	C27—C24—C26	113.1 (6)
C2—C7—C6	119.6 (3)	O6—C24—C26	101.7 (6)
C2—C7—C8	120.3 (2)	C25'—C24—C26	134.1 (8)
C6—C7—C8	120.0 (3)	C26'—C24—C26	24.4 (7)
O2—C8—C7	120.6 (3)	C27—C24—C27'	38.5 (5)
O2—C8—C9	121.2 (3)	O6—C24—C27'	97.1 (6)
C7—C8—C9	118.3 (2)	C25'—C24—C27'	110.5 (6)
C10—C9—C14	121.6 (3)	C26'—C24—C27'	112.1 (6)
C10—C9—C8	116.8 (2)	C26—C24—C27'	89.2 (7)
C14—C9—C8	121.6 (2)	C27—C24—C25	109.9 (6)
C11—C10—C9	121.5 (3)	O6—C24—C25	102.7 (5)
C11—C10—H10	119.3	C25'—C24—C25	38.3 (6)
C9—C10—H10	119.3	C26'—C24—C25	85.8 (7)
C12—C11—C10	117.5 (3)	C26—C24—C25	110.1 (6)
C12—C11—H11	121.3	C27'—C24—C25	148.4 (6)
C10—C11—H11	121.3	C24—C25—H25A	109.5
C11—C12—N2	128.4 (3)	C24—C25—H25B	109.5
C11—C12—C13	123.3 (3)	H25A—C25—H25B	109.5
N2—C12—C13	108.3 (2)	C24—C25—H25C	109.5
N1—C13—C14	135.4 (2)	H25A—C25—H25C	109.5
N1—C13—C12	105.6 (2)	H25B—C25—H25C	109.5
C14—C13—C12	119.0 (2)	C24—C26—H26A	109.5
C13—C14—C9	117.1 (2)	C24—C26—H26B	109.5
C13—C14—C1	124.2 (2)	H26A—C26—H26B	109.5
C9—C14—C1	118.7 (2)	C24—C26—H26C	109.5
O3—C15—N2	127.4 (3)	H26A—C26—H26C	109.5
O3—C15—N1	126.2 (3)	H26B—C26—H26C	109.5
N2—C15—N1	106.4 (2)	C24—C27—H27A	109.5
N1—C16—C17	112.6 (2)	C24—C27—H27B	109.5
N1—C16—H16A	109.1	H27A—C27—H27B	109.5
C17—C16—H16A	109.1	C24—C27—H27C	109.5
N1—C16—H16B	109.1	H27A—C27—H27C	109.5
C17—C16—H16B	109.1	H27B—C27—H27C	109.5
H16A—C16—H16B	107.8	C24—C25'—H25D	109.5
O5—C17—O4	126.3 (3)	C24—C25'—H25E	109.5
O5—C17—C16	124.8 (3)	H25D—C25'—H25E	109.5
O4—C17—C16	108.9 (2)	C24—C25'—H25F	109.5
O4—C18—C19	110.2 (3)	H25D—C25'—H25F	109.5
O4—C18—C20	102.6 (3)	H25E—C25'—H25F	109.5
C19—C18—C20	112.3 (3)	C24—C26'—H26D	109.5
O4—C18—C21	108.3 (3)	C24—C26'—H26E	109.5
C19—C18—C21	113.2 (3)	H26D—C26'—H26E	109.5
C20—C18—C21	109.6 (3)	C24—C26'—H26F	109.5
C18—C19—H19A	109.5	H26D—C26'—H26F	109.5
C18—C19—H19B	109.5	H26E—C26'—H26F	109.5
H19A—C19—H19B	109.5	C24—C27'—H27D	109.5
C18—C19—H19C	109.5	C24—C27'—H27E	109.5
H19A—C19—H19C	109.5	H27D—C27'—H27E	109.5
H19B—C19—H19C	109.5	C24—C27'—H27F	109.5
C18—C20—H20A	109.5	H27D—C27'—H27F	109.5
C18—C20—H20B	109.5	H27E—C27'—H27F	109.5

O1—C1—C2—C3	12.3 (4)	C12—C13—C14—C9	−0.4 (4)
C14—C1—C2—C3	−170.7 (3)	N1—C13—C14—C1	−3.7 (5)
O1—C1—C2—C7	−165.2 (3)	C12—C13—C14—C1	177.7 (3)
C14—C1—C2—C7	11.8 (4)	C10—C9—C14—C13	0.6 (4)
C7—C2—C3—C4	−1.4 (5)	C8—C9—C14—C13	−180.0 (2)
C1—C2—C3—C4	−178.9 (3)	C10—C9—C14—C1	−177.5 (3)
C2—C3—C4—C5	1.8 (5)	C8—C9—C14—C1	1.9 (4)
C3—C4—C5—C6	−0.4 (5)	O1—C1—C14—C13	−11.4 (5)
C4—C5—C6—C7	−1.4 (5)	C2—C1—C14—C13	171.7 (3)
C3—C2—C7—C6	−0.5 (4)	O1—C1—C14—C9	166.6 (3)
C1—C2—C7—C6	177.0 (3)	C2—C1—C14—C9	−10.3 (4)
C3—C2—C7—C8	178.0 (3)	C12—N2—C15—O3	−176.3 (3)
C1—C2—C7—C8	−4.5 (4)	C22—N2—C15—O3	−8.1 (5)
C5—C6—C7—C2	1.9 (4)	C12—N2—C15—N1	3.4 (3)
C5—C6—C7—C8	−176.6 (3)	C22—N2—C15—N1	171.6 (2)
C2—C7—C8—O2	177.6 (3)	C13—N1—C15—O3	177.0 (3)
C6—C7—C8—O2	−3.9 (4)	C16—N1—C15—O3	−0.5 (4)
C2—C7—C8—C9	−4.0 (4)	C13—N1—C15—N2	−2.8 (3)
C6—C7—C8—C9	174.5 (3)	C16—N1—C15—N2	179.8 (2)
O2—C8—C9—C10	3.1 (4)	C13—N1—C16—C17	−62.9 (4)
C7—C8—C9—C10	−175.2 (3)	C15—N1—C16—C17	113.8 (3)
O2—C8—C9—C14	−176.3 (3)	C18—O4—C17—O5	9.9 (5)
C7—C8—C9—C14	5.3 (4)	C18—O4—C17—C16	−170.1 (3)
C14—C9—C10—C11	−0.9 (4)	N1—C16—C17—O5	−5.5 (4)
C8—C9—C10—C11	179.7 (3)	N1—C16—C17—O4	174.5 (2)
C9—C10—C11—C12	0.9 (4)	C17—O4—C18—C19	−65.4 (4)
C10—C11—C12—N2	179.7 (3)	C17—O4—C18—C20	174.8 (3)
C10—C11—C12—C13	−0.6 (4)	C17—O4—C18—C21	59.0 (4)
C15—N2—C12—C11	176.8 (3)	C15—N2—C22—C23	−92.2 (3)
C22—N2—C12—C11	9.2 (5)	C12—N2—C22—C23	73.9 (4)
C15—N2—C12—C13	−2.9 (3)	C24—O6—C23—O7	−6.9 (6)
C22—N2—C12—C13	−170.5 (3)	C24—O6—C23—C22	173.9 (4)
C15—N1—C13—C14	−177.8 (3)	N2—C22—C23—O7	8.9 (5)
C16—N1—C13—C14	−0.9 (5)	N2—C22—C23—O6	−171.9 (3)
C15—N1—C13—C12	1.0 (3)	C23—O6—C24—C27	41.5 (8)
C16—N1—C13—C12	177.9 (3)	C23—O6—C24—C25'	−41.3 (8)
C11—C12—C13—N1	−178.6 (3)	C23—O6—C24—C26'	−169.1 (6)
N2—C12—C13—N1	1.1 (3)	C23—O6—C24—C26	166.2 (6)
C11—C12—C13—C14	0.4 (4)	C23—O6—C24—C27'	75.5 (6)
N2—C12—C13—C14	−179.9 (2)	C23—O6—C24—C25	−79.8 (6)
N1—C13—C14—C9	178.3 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16B···O2ⁱ	0.97	2.54	3.320 (4)	137
C22—H22A···O5ⁱ	0.97	2.47	3.391 (3)	159
C22—H22B···O7ⁱ	0.97	2.29	3.190 (4)	154

Symmetry code: (i) x, −y+3/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₂₇H₂₈N₂O₇
M_r	492.51
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	19.5785 (4), 13.0330 (3), 9.9269 (2)
β (°)	90.583 (1)
V (Å³)	2532.88 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.50 × 0.10 × 0.10

Data collection
Diffractometer	Bruker APEXII diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	37371, 5172, 2929
R_int	0.070
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.056, 0.190, 1.04
No. of reflections	5172
No. of parameters	353
No. of restraints	48
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.51, −0.31

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16B···O2ⁱ	0.97	2.54	3.320 (4)	137
C22—H22A···O5ⁱ	0.97	2.47	3.391 (3)	159
C22—H22B···O7ⁱ	0.97	2.29	3.190 (4)	154

Symmetry code: (i) x, −y+3/2, z−1/2.

Acknowledgements

We thank Université Sidi Mohamed Ben Abdallah, Université Mohammed V-Agdal and the University of Malaya for supporting this study.

References

Afrakssou, Z., Rodi, Y. K., Zouihri, H., Essassi, E. M. & Ng, S. W. (2010). Acta Cryst. E66, o1851. Web of Science CSD CrossRef IUCr Journals Google Scholar
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Di-tert-butyl 2,6,11-trioxo-2,3-di­hydro-1H-anthra[1,2-d]imidazole-1,3-di­acetate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

Di-tert-butyl 2,6,11-trioxo-2,3-dihydro-1H-anthra[1,2-d]imidazole-1,3-diacetate