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

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ISSN: 2056-9890

Ethyl 2-{4-[(1,5-di­benzyl-2,4-dioxo-2,3,4,5-tetra­hydro-1H-1,5-benzo­diazepin-3-yl)meth­yl]-1H-1,2,3-triazol-1-yl}acetate

aLaboratoire de Chimie Organique Appliquée, Faculté des Sciences et Techniques, Université Sidi Mohamed Ben Abdallah, Fés, Morocco, bService de Diffraction X, Laboratoire de Chimie de Coordination, 205 route de Narbonne, 31077 Toulouse Cedex 04, 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 7 December 2009; accepted 8 December 2009; online 12 December 2009)

The reaction of 1,5-dibenzyl-3-propargyl-1,5-benzodiazepine-2,4-dione with ethyl azido­acetate in the presence of copper sulfate pentahydrate and sodium ascorbate leads to the formation of the title regioisomer, C30H29N5O4, which features a phenyl­ene ring fused with a seven-membered diazepinyl ring. The latter ring adopts a boat conformation (with the methyl­triazolylacetate-bearing C atom as the prow and the fused-ring C atoms as the stern). The benzyl groups connected to the diazepinyl ring jprotrude from the sides; the methyl­triazolylacetate substituent occupies an axial position.

Related literature

For the crystal structure of the parent compound, benzodiazepin-2,4-dione, see: Négrier et al. (2006[Négrier, Ph., Mondieig, D., Léger, J. M., Benali, B., Lazar, Z., Boucetta, A., Elassyry, A., Lakhrissi, B., Jermoumi, C. & Massoui, M. (2006). X-ray Struct. Anal. Online, 22, x175-x176.]). For the crystal structure of 1,5-dibenzyl-3-propargyl-1,5-benzodiazepine-2,4-dione, see: Jabli et al. (2009[Jabli, H., Ouazzani Chahdi, F., Garrigues, B., Essassi, E. M. & Ng, S. W. (2009). Acta Cryst. E65, o3149.]).

[Scheme 1]

Experimental

Crystal data
  • C30H29N5O4

  • Mr = 523.58

  • Monoclinic, P 21 /c

  • a = 14.2015 (5) Å

  • b = 10.9337 (4) Å

  • c = 17.9368 (6) Å

  • β = 95.699 (2)°

  • V = 2771.37 (17) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 243 K

  • 0.30 × 0.22 × 0.08 mm

Data collection
  • Bruker APEXII diffractometer

  • 29097 measured reflections

  • 6377 independent reflections

  • 2690 reflections with I > 2σ(I)

  • Rint = 0.079

  • Standard reflections: 0

Refinement
  • R[F2 > 2σ(F2)] = 0.058

  • wR(F2) = 0.174

  • S = 1.00

  • 6377 reflections

  • 352 parameters

  • 1 restraint

  • H-atom parameters constrained

  • Δρmax = 0.48 e Å−3

  • Δρmin = −0.22 e Å−3

Data collection: APEX2 (Bruker, 2005[Bruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2005[Bruker (2005). 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, 2009[Westrip, S. P. (2009). publCIF. In preparation.]).

Supporting information


Related literature top

For the crystal structure of the parent compound, benzodiazepin-2,4-dione, see: Négrier et al. (2006). For the crystal structure of 1,5-dibenzyl-3-propargyl-1,5-benzodiazepine-2,4-dione, see: Jabli et al. (2009).

Experimental top

To a solution 1,5-dibenzyl-1,5-benzodiazepine-2,4-dione (1 mmol) t-butyl alcohol/water (1/2, 8 ml) was added copper sulfate pentahydrate (1 mmol), sodium ascorbate (2 mmol) and ethyl azidoacetate (5 mmol). Stirring was continued for 8 h. The solution was diluted with water (20 ml) and the organic compound extracted with ethyl acetate (2 x 20 ml). The extracts were washed with brine and dried over sodium sulfate. The compound was recrystallized from ether to give colorless crystals.

Refinement top

Carbon-bound H-atoms were placed in calculated positions (C—H 0.94 to 0.98 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2–1.5U(C).

The carbon-carbon distance in the ethyl end of the molecule was tightly restrained to 1.540±0.005 Å. Attempts to model this unit as being disordered over two sites required a large number of restraints.

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, 2009).

Figures top
[Figure 1] Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of C30H29N5O4 at the 70% probability level; hydrogen atoms are drawn as arbitrary radius.
Ethyl 2-{4-[(1,5-dibenzyl-2,4-dioxo-2,3,4,5-tetrahydro-1H-1,5- benzodiazepin-3-yl)methyl]-1H-1,2,3-triazol-1-yl}acetate top
Crystal data top
C30H29N5O4F(000) = 1104
Mr = 523.58Dx = 1.255 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2371 reflections
a = 14.2015 (5) Åθ = 2.2–18.1°
b = 10.9337 (4) ŵ = 0.09 mm1
c = 17.9368 (6) ÅT = 243 K
β = 95.699 (2)°Block, colorless
V = 2771.37 (17) Å30.30 × 0.22 × 0.08 mm
Z = 4
Data collection top
Bruker APEXII
diffractometer
2690 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.079
Graphite monochromatorθmax = 27.5°, θmin = 1.4°
ϕ and ω scansh = 1518
29097 measured reflectionsk = 1114
6377 independent reflectionsl = 2323
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)] = 0.058Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.174H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.0719P)2 + 0.0345P]
where P = (Fo2 + 2Fc2)/3
6377 reflections(Δ/σ)max = 0.001
352 parametersΔρmax = 0.48 e Å3
1 restraintΔρmin = 0.22 e Å3
Crystal data top
C30H29N5O4V = 2771.37 (17) Å3
Mr = 523.58Z = 4
Monoclinic, P21/cMo Kα radiation
a = 14.2015 (5) ŵ = 0.09 mm1
b = 10.9337 (4) ÅT = 243 K
c = 17.9368 (6) Å0.30 × 0.22 × 0.08 mm
β = 95.699 (2)°
Data collection top
Bruker APEXII
diffractometer
2690 reflections with I > 2σ(I)
29097 measured reflectionsRint = 0.079
6377 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0581 restraint
wR(F2) = 0.174H-atom parameters constrained
S = 1.00Δρmax = 0.48 e Å3
6377 reflectionsΔρmin = 0.22 e Å3
352 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.37697 (14)1.09779 (17)0.39010 (11)0.0567 (6)
O20.11543 (14)1.08866 (18)0.41866 (11)0.0600 (6)
O30.70046 (15)0.63752 (18)0.54560 (12)0.0665 (6)
O40.60809 (16)0.7150 (2)0.44777 (13)0.0844 (8)
N10.31956 (15)1.0200 (2)0.27730 (12)0.0482 (6)
N20.11754 (15)1.0312 (2)0.29647 (12)0.0483 (6)
N30.31787 (17)0.7234 (2)0.46224 (13)0.0557 (7)
N40.38706 (18)0.6481 (2)0.48645 (13)0.0576 (7)
N50.45203 (16)0.7143 (2)0.52910 (12)0.0484 (6)
C10.2513 (2)0.9476 (3)0.23315 (14)0.0471 (7)
C20.2827 (3)0.8723 (3)0.17821 (18)0.0732 (10)
H20.34780.86580.17350.088*
C30.2187 (3)0.8067 (4)0.1304 (2)0.0931 (13)
H30.24040.75520.09380.112*
C40.1223 (3)0.8172 (3)0.13675 (19)0.0830 (11)
H40.07860.77530.10310.100*
C50.0908 (2)0.8889 (3)0.19218 (16)0.0630 (9)
H50.02560.89340.19710.076*
C60.1540 (2)0.9551 (2)0.24119 (14)0.0455 (7)
C70.38849 (19)1.0938 (3)0.23979 (16)0.0544 (8)
H7A0.38871.17680.26040.065*
H7B0.36581.09960.18650.065*
C80.49003 (19)1.0480 (2)0.24595 (15)0.0459 (7)
C90.5521 (2)1.1034 (3)0.20078 (16)0.0561 (8)
H90.52941.16430.16660.067*
C100.6470 (2)1.0702 (3)0.2054 (2)0.0703 (10)
H100.68751.10730.17370.084*
C110.6819 (2)0.9829 (3)0.25645 (19)0.0705 (9)
H110.74640.96180.26040.085*
C120.6217 (2)0.9267 (3)0.30160 (18)0.0628 (9)
H120.64510.86670.33620.075*
C130.5257 (2)0.9588 (3)0.29596 (16)0.0558 (8)
H130.48490.91940.32650.067*
C140.0279 (2)1.0971 (3)0.27638 (17)0.0630 (9)
H14A0.01491.14990.31830.076*
H14B0.02371.03750.26880.076*
C150.0286 (2)1.1742 (3)0.20694 (15)0.0498 (7)
C160.0512 (2)1.1786 (3)0.15552 (17)0.0598 (8)
H160.10451.13140.16360.072*
C170.0530 (3)1.2522 (3)0.09205 (19)0.0702 (10)
H170.10711.25380.05740.084*
C180.0242 (3)1.3224 (3)0.08008 (19)0.0728 (10)
H180.02271.37200.03720.087*
C190.1046 (2)1.3204 (3)0.1311 (2)0.0711 (9)
H190.15721.36890.12310.085*
C200.1064 (2)1.2457 (3)0.19446 (18)0.0637 (9)
H200.16071.24380.22890.076*
C210.32027 (19)1.0305 (2)0.35331 (16)0.0449 (7)
C220.24439 (18)0.9589 (2)0.38906 (14)0.0408 (6)
H220.23730.87740.36520.049*
C230.15274 (19)1.0309 (2)0.37117 (16)0.0456 (7)
C240.27037 (19)0.9424 (2)0.47331 (14)0.0475 (7)
H24A0.29861.01810.49450.057*
H24B0.21290.92600.49770.057*
C250.33895 (19)0.8388 (2)0.48895 (14)0.0424 (7)
C260.4240 (2)0.8323 (2)0.53126 (15)0.0493 (7)
H260.45670.89690.55680.059*
C270.5400 (2)0.6571 (3)0.56053 (16)0.0526 (8)
H27A0.52940.56950.56740.063*
H27B0.55940.69270.60980.063*
C280.6185 (2)0.6746 (3)0.51023 (19)0.0557 (8)
C290.7809 (2)0.6436 (4)0.5009 (2)0.0954 (13)
H29A0.79790.72910.49280.114*
H29B0.76450.60520.45200.114*
C300.8613 (3)0.5788 (4)0.5417 (3)0.155 (2)
H30A0.91540.58190.51270.232*
H30B0.84410.49420.54930.232*
H30C0.87740.61770.58990.232*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0539 (13)0.0544 (12)0.0612 (13)0.0108 (10)0.0030 (11)0.0064 (10)
O20.0620 (14)0.0655 (13)0.0542 (13)0.0135 (11)0.0145 (11)0.0095 (11)
O30.0555 (14)0.0591 (14)0.0836 (16)0.0036 (11)0.0003 (13)0.0102 (11)
O40.0740 (17)0.120 (2)0.0600 (15)0.0123 (14)0.0093 (13)0.0211 (14)
N10.0452 (14)0.0583 (15)0.0424 (14)0.0054 (12)0.0108 (12)0.0026 (11)
N20.0456 (14)0.0554 (14)0.0442 (14)0.0092 (11)0.0058 (11)0.0036 (11)
N30.0560 (16)0.0506 (15)0.0588 (16)0.0016 (13)0.0017 (13)0.0098 (12)
N40.0586 (17)0.0468 (14)0.0656 (17)0.0035 (13)0.0027 (14)0.0102 (13)
N50.0538 (15)0.0400 (13)0.0500 (14)0.0046 (12)0.0013 (12)0.0011 (11)
C10.0504 (19)0.0582 (18)0.0341 (15)0.0024 (15)0.0103 (14)0.0017 (13)
C20.074 (2)0.092 (3)0.059 (2)0.005 (2)0.0277 (19)0.0179 (19)
C30.106 (3)0.117 (3)0.060 (2)0.021 (3)0.029 (2)0.041 (2)
C40.096 (3)0.107 (3)0.047 (2)0.036 (2)0.010 (2)0.022 (2)
C50.063 (2)0.080 (2)0.0463 (19)0.0135 (18)0.0049 (17)0.0028 (17)
C60.0501 (19)0.0516 (17)0.0346 (15)0.0020 (14)0.0037 (14)0.0011 (13)
C70.0527 (19)0.0597 (19)0.0523 (18)0.0017 (15)0.0127 (15)0.0151 (14)
C80.0487 (18)0.0422 (16)0.0476 (17)0.0058 (14)0.0077 (14)0.0022 (14)
C90.055 (2)0.0580 (19)0.0560 (19)0.0057 (16)0.0088 (16)0.0116 (15)
C100.053 (2)0.078 (2)0.082 (2)0.0051 (18)0.0116 (19)0.0160 (19)
C110.055 (2)0.077 (2)0.081 (2)0.0072 (18)0.012 (2)0.007 (2)
C120.068 (2)0.0550 (19)0.066 (2)0.0146 (17)0.0066 (18)0.0096 (16)
C130.064 (2)0.0494 (18)0.0564 (19)0.0017 (16)0.0162 (16)0.0082 (15)
C140.0445 (19)0.079 (2)0.066 (2)0.0117 (16)0.0066 (16)0.0145 (17)
C150.0445 (18)0.0548 (18)0.0497 (18)0.0076 (15)0.0027 (15)0.0049 (14)
C160.051 (2)0.065 (2)0.064 (2)0.0076 (16)0.0083 (17)0.0019 (17)
C170.067 (2)0.081 (3)0.061 (2)0.020 (2)0.0015 (19)0.0083 (18)
C180.095 (3)0.067 (2)0.058 (2)0.022 (2)0.016 (2)0.0151 (17)
C190.071 (2)0.067 (2)0.078 (2)0.0035 (18)0.019 (2)0.0073 (19)
C200.055 (2)0.069 (2)0.067 (2)0.0023 (17)0.0032 (17)0.0048 (17)
C210.0426 (17)0.0426 (16)0.0500 (18)0.0038 (14)0.0067 (15)0.0001 (14)
C220.0447 (16)0.0393 (15)0.0391 (15)0.0020 (13)0.0082 (13)0.0030 (12)
C230.0482 (18)0.0458 (16)0.0438 (17)0.0001 (14)0.0102 (15)0.0004 (13)
C240.0536 (18)0.0520 (17)0.0372 (15)0.0009 (14)0.0068 (14)0.0028 (13)
C250.0478 (18)0.0437 (16)0.0359 (15)0.0039 (14)0.0048 (14)0.0012 (12)
C260.059 (2)0.0362 (16)0.0519 (18)0.0065 (14)0.0006 (16)0.0020 (13)
C270.059 (2)0.0411 (16)0.0550 (18)0.0026 (14)0.0058 (16)0.0086 (14)
C280.056 (2)0.0488 (18)0.061 (2)0.0044 (15)0.0026 (18)0.0041 (15)
C290.060 (2)0.110 (3)0.118 (3)0.012 (2)0.017 (3)0.013 (3)
C300.089 (3)0.141 (5)0.235 (7)0.038 (3)0.021 (4)0.056 (4)
Geometric parameters (Å, º) top
O1—C211.233 (3)C11—H110.9400
O2—C231.223 (3)C12—C131.402 (4)
O3—C281.333 (3)C12—H120.9400
O3—C291.461 (4)C13—H130.9400
O4—C281.200 (3)C14—C151.504 (4)
N1—C211.367 (3)C14—H14A0.9800
N1—C11.429 (3)C14—H14B0.9800
N1—C71.481 (3)C15—C161.388 (4)
N2—C231.383 (3)C15—C201.390 (4)
N2—C61.430 (3)C16—C171.392 (4)
N2—C141.477 (3)C16—H160.9400
N3—N41.322 (3)C17—C181.372 (5)
N3—C251.371 (3)C17—H170.9400
N4—N51.350 (3)C18—C191.391 (5)
N5—C261.351 (3)C18—H180.9400
N5—C271.460 (3)C19—C201.397 (4)
C1—C21.391 (4)C19—H190.9400
C1—C61.405 (4)C20—H200.9400
C2—C31.385 (5)C21—C221.524 (4)
C2—H20.9400C22—C231.528 (4)
C3—C41.389 (5)C22—C241.530 (3)
C3—H30.9400C22—H220.9900
C4—C51.376 (4)C24—C251.502 (4)
C4—H40.9400C24—H24A0.9800
C5—C61.395 (4)C24—H24B0.9800
C5—H50.9400C25—C261.363 (4)
C7—C81.520 (4)C26—H260.9400
C7—H7A0.9800C27—C281.513 (4)
C7—H7B0.9800C27—H27A0.9800
C8—C131.386 (4)C27—H27B0.9800
C8—C91.394 (4)C29—C301.475 (4)
C9—C101.390 (4)C29—H29A0.9800
C9—H90.9400C29—H29B0.9800
C10—C111.381 (4)C30—H30A0.9700
C10—H100.9400C30—H30B0.9700
C11—C121.379 (4)C30—H30C0.9700
C28—O3—C29114.8 (3)C20—C15—C14121.3 (3)
C21—N1—C1122.5 (2)C15—C16—C17120.7 (3)
C21—N1—C7117.9 (2)C15—C16—H16119.6
C1—N1—C7119.5 (2)C17—C16—H16119.6
C23—N2—C6123.3 (2)C18—C17—C16120.1 (3)
C23—N2—C14117.2 (2)C18—C17—H17120.0
C6—N2—C14118.5 (2)C16—C17—H17120.0
N4—N3—C25109.2 (2)C17—C18—C19120.3 (3)
N3—N4—N5107.2 (2)C17—C18—H18119.9
N4—N5—C26110.0 (2)C19—C18—H18119.9
N4—N5—C27120.0 (2)C18—C19—C20119.5 (3)
C26—N5—C27129.9 (2)C18—C19—H19120.3
C2—C1—C6119.6 (3)C20—C19—H19120.3
C2—C1—N1118.2 (3)C15—C20—C19120.6 (3)
C6—C1—N1122.1 (2)C15—C20—H20119.7
C3—C2—C1120.5 (3)C19—C20—H20119.7
C3—C2—H2119.7O1—C21—N1121.6 (3)
C1—C2—H2119.7O1—C21—C22122.2 (2)
C2—C3—C4119.8 (3)N1—C21—C22116.2 (2)
C2—C3—H3120.1C21—C22—C23105.7 (2)
C4—C3—H3120.1C21—C22—C24111.4 (2)
C5—C4—C3120.0 (3)C23—C22—C24112.6 (2)
C5—C4—H4120.0C21—C22—H22109.0
C3—C4—H4120.0C23—C22—H22109.0
C4—C5—C6121.1 (3)C24—C22—H22109.0
C4—C5—H5119.5O2—C23—N2122.3 (3)
C6—C5—H5119.5O2—C23—C22122.6 (2)
C5—C6—C1118.9 (3)N2—C23—C22115.0 (2)
C5—C6—N2118.9 (3)C25—C24—C22111.2 (2)
C1—C6—N2122.2 (2)C25—C24—H24A109.4
N1—C7—C8116.9 (2)C22—C24—H24A109.4
N1—C7—H7A108.1C25—C24—H24B109.4
C8—C7—H7A108.1C22—C24—H24B109.4
N1—C7—H7B108.1H24A—C24—H24B108.0
C8—C7—H7B108.1C26—C25—N3107.3 (2)
H7A—C7—H7B107.3C26—C25—C24131.7 (2)
C13—C8—C9118.1 (3)N3—C25—C24120.9 (2)
C13—C8—C7124.2 (3)N5—C26—C25106.3 (2)
C9—C8—C7117.7 (2)N5—C26—H26126.8
C10—C9—C8121.2 (3)C25—C26—H26126.8
C10—C9—H9119.4N5—C27—C28111.6 (2)
C8—C9—H9119.4N5—C27—H27A109.3
C11—C10—C9120.1 (3)C28—C27—H27A109.3
C11—C10—H10119.9N5—C27—H27B109.3
C9—C10—H10119.9C28—C27—H27B109.3
C10—C11—C12119.7 (3)H27A—C27—H27B108.0
C10—C11—H11120.2O4—C28—O3125.2 (3)
C12—C11—H11120.2O4—C28—C27125.0 (3)
C11—C12—C13120.1 (3)O3—C28—C27109.7 (3)
C11—C12—H12120.0O3—C29—C30108.4 (3)
C13—C12—H12120.0O3—C29—H29A110.0
C8—C13—C12120.9 (3)C30—C29—H29A110.0
C8—C13—H13119.6O3—C29—H29B110.0
C12—C13—H13119.6C30—C29—H29B110.0
N2—C14—C15113.5 (2)H29A—C29—H29B108.4
N2—C14—H14A108.9C29—C30—H30A109.5
C15—C14—H14A108.9C29—C30—H30B109.5
N2—C14—H14B108.9H30A—C30—H30B109.5
C15—C14—H14B108.9C29—C30—H30C109.5
H14A—C14—H14B107.7H30A—C30—H30C109.5
C16—C15—C20118.8 (3)H30B—C30—H30C109.5
C16—C15—C14119.9 (3)
C25—N3—N4—N50.5 (3)C15—C16—C17—C180.6 (5)
N3—N4—N5—C260.5 (3)C16—C17—C18—C190.0 (5)
N3—N4—N5—C27176.5 (2)C17—C18—C19—C200.4 (5)
C21—N1—C1—C2135.6 (3)C16—C15—C20—C190.3 (4)
C7—N1—C1—C248.8 (4)C14—C15—C20—C19177.5 (3)
C21—N1—C1—C647.6 (4)C18—C19—C20—C150.3 (5)
C7—N1—C1—C6128.0 (3)C1—N1—C21—O1176.6 (2)
C6—C1—C2—C31.4 (5)C7—N1—C21—O10.9 (4)
N1—C1—C2—C3175.5 (3)C1—N1—C21—C220.8 (4)
C1—C2—C3—C40.8 (6)C7—N1—C21—C22176.5 (2)
C2—C3—C4—C52.5 (6)O1—C21—C22—C23101.2 (3)
C3—C4—C5—C62.1 (5)N1—C21—C22—C2376.1 (3)
C4—C5—C6—C10.0 (4)O1—C21—C22—C2421.4 (3)
C4—C5—C6—N2178.2 (3)N1—C21—C22—C24161.2 (2)
C2—C1—C6—C51.8 (4)C6—N2—C23—O2173.5 (2)
N1—C1—C6—C5175.0 (2)C14—N2—C23—O24.5 (4)
C2—C1—C6—N2179.8 (3)C6—N2—C23—C229.6 (4)
N1—C1—C6—N23.1 (4)C14—N2—C23—C22178.7 (2)
C23—N2—C6—C5132.3 (3)C21—C22—C23—O2108.4 (3)
C14—N2—C6—C536.6 (4)C24—C22—C23—O213.5 (4)
C23—N2—C6—C149.6 (4)C21—C22—C23—N268.5 (3)
C14—N2—C6—C1141.4 (3)C24—C22—C23—N2169.7 (2)
C21—N1—C7—C877.6 (3)C21—C22—C24—C2580.8 (3)
C1—N1—C7—C8106.6 (3)C23—C22—C24—C25160.6 (2)
N1—C7—C8—C1313.9 (4)N4—N3—C25—C260.3 (3)
N1—C7—C8—C9169.2 (2)N4—N3—C25—C24177.0 (2)
C13—C8—C9—C100.2 (4)C22—C24—C25—C26128.0 (3)
C7—C8—C9—C10177.3 (3)C22—C24—C25—N356.2 (3)
C8—C9—C10—C111.4 (5)N4—N5—C26—C250.3 (3)
C9—C10—C11—C121.5 (5)C27—N5—C26—C25175.8 (3)
C10—C11—C12—C130.4 (5)N3—C25—C26—N50.0 (3)
C9—C8—C13—C120.9 (4)C24—C25—C26—N5176.2 (3)
C7—C8—C13—C12176.0 (3)N4—N5—C27—C2893.4 (3)
C11—C12—C13—C80.8 (5)C26—N5—C27—C2881.7 (3)
C23—N2—C14—C15136.3 (3)C29—O3—C28—O42.8 (5)
C6—N2—C14—C1554.1 (4)C29—O3—C28—C27176.7 (3)
N2—C14—C15—C16139.8 (3)N5—C27—C28—O49.6 (4)
N2—C14—C15—C2043.0 (4)N5—C27—C28—O3170.8 (2)
C20—C15—C16—C170.7 (4)C28—O3—C29—C30169.4 (3)
C14—C15—C16—C17178.0 (3)

Experimental details

Crystal data
Chemical formulaC30H29N5O4
Mr523.58
Crystal system, space groupMonoclinic, P21/c
Temperature (K)243
a, b, c (Å)14.2015 (5), 10.9337 (4), 17.9368 (6)
β (°) 95.699 (2)
V3)2771.37 (17)
Z4
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.30 × 0.22 × 0.08
Data collection
DiffractometerBruker APEXII
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
29097, 6377, 2690
Rint0.079
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.058, 0.174, 1.00
No. of reflections6377
No. of parameters352
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.48, 0.22

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2009).

 

Acknowledgements

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

References

First citationBarbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.  CrossRef CAS Google Scholar
First citationBruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationJabli, H., Ouazzani Chahdi, F., Garrigues, B., Essassi, E. M. & Ng, S. W. (2009). Acta Cryst. E65, o3149.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationNégrier, Ph., Mondieig, D., Léger, J. M., Benali, B., Lazar, Z., Boucetta, A., Elassyry, A., Lakhrissi, B., Jermoumi, C. & Massoui, M. (2006). X-ray Struct. Anal. Online, 22, x175–x176.  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. (2009). publCIF. In preparation.  Google Scholar

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