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

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ISSN: 2056-9890

1,3-Bis[3-(1,3-dioxoisoindolin-2-yl)prop­yl]-1H-anthra[1,2-d]imidazole-2,6,11(3H)-trione

aLaboratoire de Chimie Organique Appliquée, Faculté des Sciences et Techniques, Université Sidi Mohamed Ben Abdallah, Fés, Morocco, bUnité de Catalyse et de Chimie du Solide, Ecole Nationale Supérieure de Chimie de Lille, Lille, France, cLaboratoire de Chimie Organique Hétérocyclique, Pôle de Compétences Pharmacochimie, Université Mohammed V-Agdal, BP 1014 Avenue Ibn Batout, Rabat, Morocco, dDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and eChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
*Correspondence e-mail: seikweng@um.edu.my

(Received 17 July 2011; accepted 19 July 2011; online 23 July 2011)

The title compound, C37H26N4O7, is a 1H-anthra[2,1-d]imidazole-2,6,11(3H)-trione derivative having isoindolindionylpropyl substitutents attached to the imidazole N atoms. The anthraquinone fragment is buckled, the dihedral angle between the two benzene rings being 1.6 (1)°. The two isoindoline rings of the substituents of the imidazole ring are positioned on opposite sides of the five-membered ring; these are nearly mutually perpendicular [dihedral angle between isoindoline rings = 88.3 (1)°].

Related literature

For the structure of 1,3-dibenzyl-1H-anthra[1,2-d]imidazole-2,6,11(3H)-trione, see: Afrakssou et al. (2010[Afrakssou, Z., Kandri Rodi, Y., Capet, F., Essassi, E. M. & El Ammari, L. (2011). Acta Cryst. E67, o1253-o1254.]).

[Scheme 1]

Experimental

Crystal data
  • C37H26N4O7

  • Mr = 638.62

  • Triclinic, [P \overline 1]

  • a = 8.4278 (2) Å

  • b = 13.1258 (3) Å

  • c = 13.7966 (3) Å

  • α = 94.359 (1)°

  • β = 92.472 (1)°

  • γ = 105.351 (1)°

  • V = 1464.31 (6) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.10 mm−1

  • T = 293 K

  • 0.24 × 0.12 × 0.10 mm

Data collection
  • Bruker X8 APEXII diffractometer

  • 36987 measured reflections

  • 5996 independent reflections

  • 3420 reflections with I > 2σ(I)

  • Rint = 0.059

Refinement
  • R[F2 > 2σ(F2)] = 0.045

  • wR(F2) = 0.122

  • S = 0.99

  • 5996 reflections

  • 433 parameters

  • H-atom parameters constrained

  • Δρmax = 0.26 e Å−3

  • Δρmin = −0.19 e Å−3

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information


Comment top

The two nitrogen-bound H atoms of 1H-anthra [2,1-d]imidazole-2,6,11(3H)-trione can be replaced by a alkyl substitutent when the compound is reacted with an alkyl halide in a reaction catalyzed by tetra-n-butylammonium bromide; the di-benzyl substituted derivative is synthesized in such a synthesis in high yield. The study (Afrakssou et al., 2010) is now extended to the title isoindolindionylpropyl analog (Scheme I, Fig. 1). In the compound, C37H24N2O3, the anthraquinone part of the molecule is somewhat folded along the the line connecting the carbonyl bonds (dihedral angle between the two phenyl rings is 1.6 (1) °). The two isoindoline rings of the substituents of the imidazole ring are positioned on opposite sides of the five-membered ring; these are nearly perpendicular (dihedral angle between isoindoline rings is 88.3 (1) °).

Related literature top

For 1,3-dibenzyl-1H-anthra[1,2-d]imidazole-2,6,11(3H)-trione, see: Afrakssou et al. (2010).

Experimental top

To a solution of 1H-anthra [2,1-d]imidazole-2,6,11(3H)-trione (0.40 g, 1.51 mmol), potassium carbonate (0.83 g, 6.05 mmol) and tetra-n-butylammonium bromide (0.04 g, 0.15 mmol) in DMF (15 ml)) was added 2-(3-bromopropyl)isoindoline-1,3-dione (1,01 g, 3.78 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 (1/1) as eluent. Orange crystals were isolated when the solvent was allowed to evaporate.

Refinement top

H-atoms were placed in calculated positions (C—H 0.93–0.97 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2U(C).

Omitted were (0 0 1), (0 - 1 1) and (0 1 0).

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); 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
[Figure 1] Fig. 1. Anisotropic displacement ellipsoid plot (Barbour, 2001) of C37H26N4O7 at the 50% probability level; hydrogen atoms are drawn as arbitrary radius.
1,3-Bis[3-(1,3-dioxoisoindolin-2-yl)propyl]-1H- anthra[1,2-d]imidazole-2,6,11(3H)-trione top
Crystal data top
C37H26N4O7Z = 2
Mr = 638.62F(000) = 664
Triclinic, P1Dx = 1.448 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.4278 (2) ÅCell parameters from 4182 reflections
b = 13.1258 (3) Åθ = 2.3–21.6°
c = 13.7966 (3) ŵ = 0.10 mm1
α = 94.359 (1)°T = 293 K
β = 92.472 (1)°Prism, orange
γ = 105.351 (1)°0.24 × 0.12 × 0.10 mm
V = 1464.31 (6) Å3
Data collection top
Bruker X8 APEXII
diffractometer
3420 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.059
Graphite monochromatorθmax = 26.4°, θmin = 2.6°
ϕ and ω scansh = 1010
36987 measured reflectionsk = 1616
5996 independent reflectionsl = 1717
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.122H-atom parameters constrained
S = 0.99 w = 1/[σ2(Fo2) + (0.0542P)2 + 0.1461P]
where P = (Fo2 + 2Fc2)/3
5996 reflections(Δ/σ)max = 0.001
433 parametersΔρmax = 0.26 e Å3
0 restraintsΔρmin = 0.19 e Å3
Crystal data top
C37H26N4O7γ = 105.351 (1)°
Mr = 638.62V = 1464.31 (6) Å3
Triclinic, P1Z = 2
a = 8.4278 (2) ÅMo Kα radiation
b = 13.1258 (3) ŵ = 0.10 mm1
c = 13.7966 (3) ÅT = 293 K
α = 94.359 (1)°0.24 × 0.12 × 0.10 mm
β = 92.472 (1)°
Data collection top
Bruker X8 APEXII
diffractometer
3420 reflections with I > 2σ(I)
36987 measured reflectionsRint = 0.059
5996 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0450 restraints
wR(F2) = 0.122H-atom parameters constrained
S = 0.99Δρmax = 0.26 e Å3
5996 reflectionsΔρmin = 0.19 e Å3
433 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.5704 (2)0.47298 (13)0.63443 (11)0.0694 (5)
O20.8925 (2)0.66460 (14)0.34484 (13)0.0834 (6)
O30.6768 (2)0.09268 (12)0.57598 (11)0.0700 (5)
O40.56768 (19)0.10043 (13)0.05066 (11)0.0656 (5)
O51.0169 (2)0.15662 (14)0.18456 (12)0.0761 (5)
O60.3403 (2)0.29911 (13)0.84710 (13)0.0740 (5)
O70.81157 (19)0.56947 (14)0.87580 (13)0.0761 (5)
N10.7796 (2)0.19318 (13)0.44979 (11)0.0488 (5)
N20.6754 (2)0.27021 (13)0.57085 (11)0.0455 (4)
N30.7825 (2)0.02105 (13)0.14120 (11)0.0480 (4)
N40.5986 (2)0.41622 (14)0.85923 (11)0.0458 (4)
C10.8001 (2)0.29730 (16)0.43109 (13)0.0419 (5)
C20.8724 (3)0.34823 (17)0.35428 (14)0.0492 (5)
H20.91460.31250.30530.059*
C30.8798 (3)0.45430 (17)0.35264 (14)0.0491 (5)
H30.92910.49080.30180.059*
C40.8152 (2)0.50800 (16)0.42506 (14)0.0417 (5)
C50.8291 (3)0.62185 (18)0.41471 (16)0.0526 (6)
C60.7666 (3)0.68337 (16)0.49133 (15)0.0482 (5)
C70.7802 (3)0.79040 (18)0.48487 (19)0.0663 (7)
H70.82870.82360.43220.080*
C80.7220 (3)0.8473 (2)0.5563 (2)0.0753 (8)
H80.73130.91890.55180.090*
C90.6501 (3)0.7985 (2)0.6346 (2)0.0742 (8)
H90.61340.83780.68340.089*
C100.6322 (3)0.69125 (19)0.64095 (17)0.0626 (6)
H100.58080.65830.69300.075*
C110.6910 (2)0.63279 (16)0.56949 (14)0.0454 (5)
C120.6631 (3)0.51677 (17)0.57502 (14)0.0443 (5)
C130.7390 (2)0.45596 (15)0.50464 (13)0.0379 (5)
C140.7336 (2)0.34809 (15)0.50730 (13)0.0390 (5)
C150.7069 (3)0.17553 (17)0.53637 (15)0.0509 (6)
C160.8255 (3)0.11176 (17)0.38722 (14)0.0545 (6)
H16A0.84680.05830.42690.065*
H16B0.92650.14390.35720.065*
C170.6929 (3)0.05910 (18)0.30844 (15)0.0559 (6)
H17A0.66330.11320.27300.067*
H17B0.59540.02050.33830.067*
C180.7492 (3)0.01791 (17)0.23662 (15)0.0583 (6)
H18A0.84830.03140.26470.070*
H18B0.66440.08490.22810.070*
C190.6909 (3)0.02707 (17)0.05504 (15)0.0464 (5)
C200.7736 (2)0.03117 (16)0.02462 (14)0.0442 (5)
C210.7354 (3)0.01664 (19)0.12347 (16)0.0576 (6)
H210.64480.03680.15030.069*
C220.8359 (3)0.0838 (2)0.18175 (17)0.0626 (6)
H220.81220.07570.24880.075*
C230.9712 (3)0.16276 (19)0.14178 (17)0.0588 (6)
H231.03720.20690.18240.071*
C241.0101 (3)0.17735 (18)0.04189 (16)0.0552 (6)
H241.10090.23050.01480.066*
C250.9092 (2)0.11015 (16)0.01541 (14)0.0443 (5)
C260.9174 (3)0.10351 (17)0.12263 (16)0.0512 (6)
C270.6156 (3)0.27580 (16)0.66910 (13)0.0484 (5)
H27A0.56910.20450.68720.058*
H27B0.52910.31200.66910.058*
C280.7529 (3)0.33381 (17)0.74275 (14)0.0490 (5)
H28A0.79900.40490.72420.059*
H28B0.83950.29770.74180.059*
C290.6973 (3)0.34116 (19)0.84581 (14)0.0530 (6)
H29A0.63310.27160.86020.064*
H29B0.79350.36280.89140.064*
C300.4274 (3)0.38945 (19)0.85898 (14)0.0493 (5)
C310.3814 (2)0.49031 (18)0.87553 (13)0.0469 (5)
C320.2294 (3)0.5099 (2)0.88355 (16)0.0610 (6)
H320.13320.45460.87900.073*
C330.2245 (3)0.6145 (2)0.89860 (16)0.0685 (7)
H330.12330.62970.90350.082*
C340.3671 (3)0.6964 (2)0.90647 (16)0.0679 (7)
H340.36060.76600.91700.082*
C350.5202 (3)0.6767 (2)0.89889 (16)0.0620 (6)
H350.61660.73190.90430.074*
C360.5244 (2)0.57277 (18)0.88312 (14)0.0472 (5)
C370.6653 (3)0.52552 (18)0.87256 (15)0.0510 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.1019 (13)0.0556 (11)0.0652 (10)0.0393 (10)0.0356 (10)0.0145 (8)
O20.1093 (15)0.0583 (12)0.0925 (13)0.0271 (10)0.0426 (11)0.0323 (10)
O30.1239 (15)0.0381 (10)0.0533 (9)0.0289 (9)0.0149 (9)0.0073 (8)
O40.0659 (10)0.0502 (10)0.0693 (10)0.0027 (9)0.0061 (8)0.0011 (8)
O50.0816 (12)0.0678 (12)0.0598 (10)0.0074 (10)0.0119 (9)0.0057 (9)
O60.0671 (11)0.0524 (11)0.0929 (13)0.0004 (9)0.0043 (9)0.0065 (9)
O70.0459 (10)0.0699 (12)0.1047 (14)0.0042 (9)0.0047 (9)0.0001 (10)
N10.0769 (13)0.0369 (10)0.0363 (9)0.0233 (9)0.0055 (9)0.0037 (7)
N20.0698 (12)0.0332 (10)0.0358 (9)0.0186 (8)0.0067 (8)0.0003 (7)
N30.0614 (11)0.0369 (10)0.0428 (10)0.0097 (9)0.0079 (8)0.0052 (8)
N40.0468 (10)0.0469 (11)0.0435 (10)0.0125 (9)0.0083 (8)0.0004 (8)
C10.0549 (12)0.0362 (12)0.0350 (10)0.0152 (10)0.0013 (9)0.0020 (9)
C20.0593 (14)0.0503 (14)0.0388 (11)0.0173 (11)0.0075 (10)0.0027 (10)
C30.0560 (13)0.0482 (14)0.0421 (12)0.0109 (11)0.0073 (10)0.0056 (10)
C40.0451 (12)0.0377 (12)0.0419 (11)0.0115 (9)0.0021 (9)0.0032 (9)
C50.0545 (13)0.0476 (14)0.0572 (14)0.0138 (11)0.0051 (11)0.0125 (11)
C60.0519 (13)0.0353 (12)0.0579 (13)0.0151 (10)0.0078 (11)0.0024 (10)
C70.0750 (17)0.0406 (15)0.0838 (17)0.0164 (13)0.0008 (14)0.0084 (13)
C80.092 (2)0.0415 (15)0.094 (2)0.0245 (14)0.0082 (17)0.0013 (15)
C90.094 (2)0.0526 (17)0.0812 (18)0.0387 (15)0.0088 (16)0.0173 (14)
C100.0846 (17)0.0518 (15)0.0572 (14)0.0322 (13)0.0012 (12)0.0050 (11)
C110.0536 (13)0.0367 (12)0.0471 (12)0.0188 (10)0.0099 (10)0.0046 (10)
C120.0541 (13)0.0450 (13)0.0378 (11)0.0216 (10)0.0011 (10)0.0014 (9)
C130.0430 (11)0.0359 (12)0.0355 (10)0.0136 (9)0.0024 (9)0.0001 (9)
C140.0474 (12)0.0371 (12)0.0325 (10)0.0135 (9)0.0006 (9)0.0019 (9)
C150.0783 (16)0.0341 (13)0.0424 (12)0.0201 (11)0.0013 (11)0.0003 (10)
C160.0792 (16)0.0467 (14)0.0438 (12)0.0307 (12)0.0026 (11)0.0064 (10)
C170.0644 (15)0.0515 (14)0.0499 (12)0.0150 (12)0.0116 (11)0.0091 (11)
C180.0866 (17)0.0415 (13)0.0464 (12)0.0180 (12)0.0127 (12)0.0046 (10)
C190.0501 (13)0.0362 (12)0.0522 (13)0.0132 (11)0.0060 (10)0.0061 (10)
C200.0462 (12)0.0402 (12)0.0468 (12)0.0146 (10)0.0044 (10)0.0042 (9)
C210.0586 (14)0.0585 (15)0.0515 (14)0.0123 (12)0.0025 (11)0.0047 (11)
C220.0748 (17)0.0716 (18)0.0472 (13)0.0297 (15)0.0055 (12)0.0043 (12)
C230.0594 (15)0.0625 (16)0.0627 (15)0.0253 (13)0.0172 (12)0.0188 (12)
C240.0460 (13)0.0545 (15)0.0648 (15)0.0133 (11)0.0032 (11)0.0048 (12)
C250.0445 (12)0.0408 (12)0.0490 (12)0.0150 (10)0.0038 (10)0.0003 (10)
C260.0569 (14)0.0416 (13)0.0517 (13)0.0104 (11)0.0005 (11)0.0050 (10)
C270.0669 (14)0.0354 (12)0.0428 (12)0.0119 (10)0.0130 (10)0.0039 (9)
C280.0560 (13)0.0521 (14)0.0439 (12)0.0224 (11)0.0084 (10)0.0047 (10)
C290.0640 (14)0.0591 (15)0.0415 (12)0.0263 (12)0.0058 (10)0.0026 (10)
C300.0521 (14)0.0520 (15)0.0386 (11)0.0056 (11)0.0041 (10)0.0016 (10)
C310.0471 (13)0.0558 (14)0.0365 (11)0.0128 (11)0.0057 (9)0.0026 (10)
C320.0497 (14)0.0784 (19)0.0524 (13)0.0155 (13)0.0014 (11)0.0026 (12)
C330.0639 (16)0.100 (2)0.0486 (14)0.0408 (16)0.0043 (12)0.0118 (14)
C340.0821 (19)0.0726 (19)0.0551 (14)0.0400 (16)0.0119 (13)0.0162 (13)
C350.0685 (16)0.0545 (16)0.0581 (14)0.0144 (13)0.0081 (12)0.0112 (11)
C360.0482 (13)0.0520 (14)0.0391 (11)0.0119 (11)0.0015 (9)0.0046 (10)
C370.0488 (13)0.0543 (15)0.0458 (12)0.0080 (11)0.0040 (10)0.0014 (10)
Geometric parameters (Å, º) top
O1—C121.226 (2)C16—C171.510 (3)
O2—C51.224 (3)C16—H16A0.9700
O3—C151.225 (2)C16—H16B0.9700
O4—C191.211 (2)C17—C181.540 (3)
O5—C261.208 (2)C17—H17A0.9700
O6—C301.213 (2)C17—H17B0.9700
O7—C371.212 (2)C18—H18A0.9700
N1—C151.373 (3)C18—H18B0.9700
N1—C11.377 (3)C19—C201.480 (3)
N1—C161.465 (2)C20—C211.375 (3)
N2—C151.392 (3)C20—C251.385 (3)
N2—C141.401 (2)C21—C221.383 (3)
N2—C271.469 (2)C21—H210.9300
N3—C261.395 (3)C22—C231.382 (3)
N3—C191.399 (2)C22—H220.9300
N3—C181.460 (3)C23—C241.390 (3)
N4—C371.390 (3)C23—H230.9300
N4—C301.392 (3)C24—C251.376 (3)
N4—C291.454 (3)C24—H240.9300
C1—C21.374 (3)C25—C261.488 (3)
C1—C141.417 (3)C27—C281.505 (3)
C2—C31.379 (3)C27—H27A0.9700
C2—H20.9300C27—H27B0.9700
C3—C41.391 (3)C28—C291.521 (3)
C3—H30.9300C28—H28A0.9700
C4—C131.424 (3)C28—H28B0.9700
C4—C51.486 (3)C29—H29A0.9700
C5—C61.480 (3)C29—H29B0.9700
C6—C71.389 (3)C30—C311.479 (3)
C6—C111.398 (3)C31—C321.379 (3)
C7—C81.376 (3)C31—C361.384 (3)
C7—H70.9300C32—C331.385 (3)
C8—C91.378 (4)C32—H320.9300
C8—H80.9300C33—C341.378 (4)
C9—C101.386 (3)C33—H330.9300
C9—H90.9300C34—C351.388 (3)
C10—C111.391 (3)C34—H340.9300
C10—H100.9300C35—C361.375 (3)
C11—C121.487 (3)C35—H350.9300
C12—C131.481 (3)C36—C371.486 (3)
C13—C141.408 (3)
C15—N1—C1109.88 (16)C17—C18—H18A108.8
C15—N1—C16124.23 (18)N3—C18—H18B108.8
C1—N1—C16125.89 (17)C17—C18—H18B108.8
C15—N2—C14109.76 (16)H18A—C18—H18B107.7
C15—N2—C27117.23 (17)O4—C19—N3124.8 (2)
C14—N2—C27132.17 (16)O4—C19—C20129.10 (19)
C26—N3—C19111.35 (17)N3—C19—C20106.09 (17)
C26—N3—C18124.79 (17)C21—C20—C25121.1 (2)
C19—N3—C18123.59 (17)C21—C20—C19130.41 (19)
C37—N4—C30111.15 (18)C25—C20—C19108.54 (17)
C37—N4—C29123.58 (18)C20—C21—C22118.0 (2)
C30—N4—C29125.26 (18)C20—C21—H21121.0
C2—C1—N1128.55 (18)C22—C21—H21121.0
C2—C1—C14123.38 (19)C21—C22—C23121.0 (2)
N1—C1—C14108.07 (17)C21—C22—H22119.5
C1—C2—C3117.46 (19)C23—C22—H22119.5
C1—C2—H2121.3C22—C23—C24121.1 (2)
C3—C2—H2121.3C22—C23—H23119.4
C2—C3—C4121.64 (19)C24—C23—H23119.4
C2—C3—H3119.2C25—C24—C23117.5 (2)
C4—C3—H3119.2C25—C24—H24121.3
C3—C4—C13121.45 (19)C23—C24—H24121.3
C3—C4—C5116.62 (18)C24—C25—C20121.42 (19)
C13—C4—C5121.93 (18)C24—C25—C26130.91 (19)
O2—C5—C6120.4 (2)C20—C25—C26107.67 (18)
O2—C5—C4120.9 (2)O5—C26—N3124.3 (2)
C6—C5—C4118.74 (19)O5—C26—C25129.3 (2)
C7—C6—C11120.0 (2)N3—C26—C25106.34 (17)
C7—C6—C5120.3 (2)N2—C27—C28111.20 (17)
C11—C6—C5119.67 (19)N2—C27—H27A109.4
C8—C7—C6120.1 (2)C28—C27—H27A109.4
C8—C7—H7120.0N2—C27—H27B109.4
C6—C7—H7120.0C28—C27—H27B109.4
C7—C8—C9120.3 (2)H27A—C27—H27B108.0
C7—C8—H8119.9C27—C28—C29113.17 (18)
C9—C8—H8119.9C27—C28—H28A108.9
C8—C9—C10120.4 (2)C29—C28—H28A108.9
C8—C9—H9119.8C27—C28—H28B108.9
C10—C9—H9119.8C29—C28—H28B108.9
C9—C10—C11120.0 (2)H28A—C28—H28B107.8
C9—C10—H10120.0N4—C29—C28112.29 (17)
C11—C10—H10120.0N4—C29—H29A109.1
C10—C11—C6119.2 (2)C28—C29—H29A109.1
C10—C11—C12119.2 (2)N4—C29—H29B109.1
C6—C11—C12121.51 (18)C28—C29—H29B109.1
O1—C12—C13121.66 (19)H29A—C29—H29B107.9
O1—C12—C11118.85 (19)O6—C30—N4123.9 (2)
C13—C12—C11119.37 (19)O6—C30—C31129.7 (2)
C14—C13—C4117.03 (17)N4—C30—C31106.47 (18)
C14—C13—C12124.79 (18)C32—C31—C36120.9 (2)
C4—C13—C12118.08 (18)C32—C31—C30130.9 (2)
N2—C14—C13135.45 (17)C36—C31—C30108.20 (18)
N2—C14—C1105.52 (16)C31—C32—C33117.9 (2)
C13—C14—C1119.03 (17)C31—C32—H32121.0
O3—C15—N1126.6 (2)C33—C32—H32121.0
O3—C15—N2126.6 (2)C34—C33—C32121.1 (2)
N1—C15—N2106.73 (18)C34—C33—H33119.5
N1—C16—C17112.36 (18)C32—C33—H33119.5
N1—C16—H16A109.1C33—C34—C35121.1 (2)
C17—C16—H16A109.1C33—C34—H34119.5
N1—C16—H16B109.1C35—C34—H34119.5
C17—C16—H16B109.1C36—C35—C34117.6 (2)
H16A—C16—H16B107.9C36—C35—H35121.2
C16—C17—C18112.01 (19)C34—C35—H35121.2
C16—C17—H17A109.2C35—C36—C31121.4 (2)
C18—C17—H17A109.2C35—C36—C37131.0 (2)
C16—C17—H17B109.2C31—C36—C37107.57 (19)
C18—C17—H17B109.2O7—C37—N4124.3 (2)
H17A—C17—H17B107.9O7—C37—C36129.1 (2)
N3—C18—C17113.82 (18)N4—C37—C36106.59 (18)
N3—C18—H18A108.8
C15—N1—C1—C2177.7 (2)C26—N3—C18—C1771.5 (3)
C16—N1—C1—C23.0 (3)C19—N3—C18—C17115.0 (2)
C15—N1—C1—C141.8 (2)C16—C17—C18—N3107.3 (2)
C16—N1—C1—C14177.54 (18)C26—N3—C19—O4179.8 (2)
N1—C1—C2—C3179.2 (2)C18—N3—C19—O45.9 (3)
C14—C1—C2—C30.2 (3)C26—N3—C19—C201.0 (2)
C1—C2—C3—C40.7 (3)C18—N3—C19—C20175.24 (18)
C2—C3—C4—C130.3 (3)O4—C19—C20—C211.5 (4)
C2—C3—C4—C5179.38 (18)N3—C19—C20—C21179.7 (2)
C3—C4—C5—O21.0 (3)O4—C19—C20—C25179.0 (2)
C13—C4—C5—O2178.7 (2)N3—C19—C20—C250.3 (2)
C3—C4—C5—C6178.26 (18)C25—C20—C21—C220.5 (3)
C13—C4—C5—C62.1 (3)C19—C20—C21—C22179.9 (2)
O2—C5—C6—C70.4 (3)C20—C21—C22—C230.4 (4)
C4—C5—C6—C7178.88 (19)C21—C22—C23—C240.2 (4)
O2—C5—C6—C11178.4 (2)C22—C23—C24—C250.2 (3)
C4—C5—C6—C112.3 (3)C23—C24—C25—C200.3 (3)
C11—C6—C7—C81.2 (3)C23—C24—C25—C26179.1 (2)
C5—C6—C7—C8180.0 (2)C21—C20—C25—C240.5 (3)
C6—C7—C8—C90.0 (4)C19—C20—C25—C24179.99 (19)
C7—C8—C9—C101.5 (4)C21—C20—C25—C26179.0 (2)
C8—C9—C10—C111.8 (4)C19—C20—C25—C260.5 (2)
C9—C10—C11—C60.5 (3)C19—N3—C26—O5178.9 (2)
C9—C10—C11—C12177.0 (2)C18—N3—C26—O54.8 (4)
C7—C6—C11—C101.0 (3)C19—N3—C26—C251.3 (2)
C5—C6—C11—C10179.78 (19)C18—N3—C26—C25175.46 (18)
C7—C6—C11—C12175.42 (19)C24—C25—C26—O50.3 (4)
C5—C6—C11—C123.4 (3)C20—C25—C26—O5179.1 (2)
C10—C11—C12—O19.8 (3)C24—C25—C26—N3179.5 (2)
C6—C11—C12—O1166.6 (2)C20—C25—C26—N31.1 (2)
C10—C11—C12—C13174.23 (18)C15—N2—C27—C28100.4 (2)
C6—C11—C12—C139.4 (3)C14—N2—C27—C2867.9 (3)
C3—C4—C13—C140.7 (3)N2—C27—C28—C29179.70 (18)
C5—C4—C13—C14179.66 (17)C37—N4—C29—C2878.3 (2)
C3—C4—C13—C12175.86 (18)C30—N4—C29—C28100.6 (2)
C5—C4—C13—C123.8 (3)C27—C28—C29—N473.0 (2)
O1—C12—C13—C149.7 (3)C37—N4—C30—O6178.8 (2)
C11—C12—C13—C14174.41 (17)C29—N4—C30—O60.2 (3)
O1—C12—C13—C4166.55 (19)C37—N4—C30—C311.2 (2)
C11—C12—C13—C49.3 (3)C29—N4—C30—C31179.77 (16)
C15—N2—C14—C13178.8 (2)O6—C30—C31—C321.1 (4)
C27—N2—C14—C139.9 (4)N4—C30—C31—C32178.8 (2)
C15—N2—C14—C10.9 (2)O6—C30—C31—C36178.9 (2)
C27—N2—C14—C1169.8 (2)N4—C30—C31—C361.1 (2)
C4—C13—C14—N2178.53 (19)C36—C31—C32—C330.5 (3)
C12—C13—C14—N25.2 (3)C30—C31—C32—C33179.6 (2)
C4—C13—C14—C11.2 (3)C31—C32—C33—C340.8 (3)
C12—C13—C14—C1175.10 (17)C32—C33—C34—C350.4 (4)
C2—C1—C14—N2179.00 (18)C33—C34—C35—C360.1 (3)
N1—C1—C14—N20.5 (2)C34—C35—C36—C310.3 (3)
C2—C1—C14—C130.8 (3)C34—C35—C36—C37179.4 (2)
N1—C1—C14—C13179.72 (16)C32—C31—C36—C350.0 (3)
C1—N1—C15—O3177.2 (2)C30—C31—C36—C35179.91 (19)
C16—N1—C15—O33.5 (4)C32—C31—C36—C37179.31 (18)
C1—N1—C15—N22.3 (2)C30—C31—C36—C370.6 (2)
C16—N1—C15—N2177.00 (18)C30—N4—C37—O7179.8 (2)
C14—N2—C15—O3177.5 (2)C29—N4—C37—O71.1 (3)
C27—N2—C15—O36.7 (3)C30—N4—C37—C360.8 (2)
C14—N2—C15—N12.0 (2)C29—N4—C37—C36179.88 (16)
C27—N2—C15—N1172.75 (17)C35—C36—C37—O70.1 (4)
C15—N1—C16—C1794.3 (2)C31—C36—C37—O7179.0 (2)
C1—N1—C16—C1784.9 (3)C35—C36—C37—N4179.1 (2)
N1—C16—C17—C18174.04 (18)C31—C36—C37—N40.1 (2)

Experimental details

Crystal data
Chemical formulaC37H26N4O7
Mr638.62
Crystal system, space groupTriclinic, P1
Temperature (K)293
a, b, c (Å)8.4278 (2), 13.1258 (3), 13.7966 (3)
α, β, γ (°)94.359 (1), 92.472 (1), 105.351 (1)
V3)1464.31 (6)
Z2
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.24 × 0.12 × 0.10
Data collection
DiffractometerBruker X8 APEXII
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
36987, 5996, 3420
Rint0.059
(sin θ/λ)max1)0.626
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.045, 0.122, 0.99
No. of reflections5996
No. of parameters433
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.26, 0.19

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

 

Acknowledgements

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

References

First citationAfrakssou, Z., Kandri Rodi, Y., Capet, F., Essassi, E. M. & El Ammari, L. (2011). Acta Cryst. E67, o1253–o1254.  Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
First citationBarbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.  CrossRef CAS Google Scholar
First citationBruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationWestrip, S. P. (2010). J. Appl. Cryst. 43, 920–925.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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