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

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ISSN: 2056-9890

1-(12-Azido-n-dodec­yl)-4-[(1,5-di­benzyl-2,4-dioxo-2,3,4,5-tetra­hydro-1H-1,5-benzodiazepin-3-yl)meth­yl]-1H-1,2,3-triazole

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 17 December 2009; accepted 17 December 2009; online 24 December 2009)

The reaction of 1,5-dibenzyl-3-propargyl-1,5-benzodiazepine-2,4-dione with 1,12-diazido-n-dodecane in the presence of catalysts leads to the formation of the title compound, C38H46N8O2. The seven-membered diazepinyl ring adopts a boat conformation with the azido­dodecyl­triazolylmethyl-bearing C atom as the prow and the fused-ring C atoms as the stern. The octyltriazolylmethyl substituent occupies an axial position.

Related literature

For the crystal structures of other N-substituted homologs, see: Jabli et al. (2009[Jabli, H., Ouazzani Chahdi, F., Garrigues, B., Essassi, E. M. & Ng, S. W. (2009). Acta Cryst. E65, o3149.], 2010[Jabli, H., Kandri Rodi, Y., Ladeira, S., Essassi, E. M. & Ng, S. W. (2010). Acta Cryst. E66, o126.]).

[Scheme 1]

Experimental

Crystal data
  • C38H46N8O2

  • Mr = 646.83

  • Triclinic, [P \overline 1]

  • a = 9.4269 (2) Å

  • b = 12.3304 (3) Å

  • c = 15.5500 (4) Å

  • α = 101.121 (2)°

  • β = 92.175 (2)°

  • γ = 92.935 (2)°

  • V = 1769.11 (7) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 193 K

  • 0.40 × 0.20 × 0.06 mm

Data collection
  • Bruker APEXII diffractometer

  • 33681 measured reflections

  • 8126 independent reflections

  • 4315 reflections with I > 2σ(I)

  • Rint = 0.076

Refinement
  • R[F2 > 2σ(F2)] = 0.052

  • wR(F2) = 0.147

  • S = 1.00

  • 8126 reflections

  • 433 parameters

  • H-atom parameters constrained

  • Δρmax = 0.21 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, 2010[Westrip, S. P. (2010). publCIF. In preparation.]).

Supporting information


Related literature top

For the crystal structures of other N-substituted homologs, see: Jabli et al. (2009, 2010).

Experimental top

To a solution 1,5-dibenzyl-3-propargyl-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 1,12-diazido-n-dodecaneoctane (5 mmol). Stirring was continued for 12 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 ethyl acetate/ether to give colorless crystals.

Refinement top

Carbon-bound H-atoms were placed in calculated positions (C—H 0.95 to 0.99 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2–1.5U(C).

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
[Figure 1] Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of C38H46N8O2 at the 70% probability level; hydrogen atoms are drawn as arbitrary radius.
1-(12-Azido-n-dodecyl)-4-[(1,5-dibenzyl-2,4-dioxo-2,3,4,5-tetrahydro-1H-1,5-benzodiazepin-3-yl)methyl]-1H-1,2,3-triazole top
Crystal data top
C38H46N8O2Z = 2
Mr = 646.83F(000) = 692
Triclinic, P1Dx = 1.214 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.4269 (2) ÅCell parameters from 3120 reflections
b = 12.3304 (3) Åθ = 2.3–22.9°
c = 15.5500 (4) ŵ = 0.08 mm1
α = 101.121 (2)°T = 193 K
β = 92.175 (2)°Plate, colorless
γ = 92.935 (2)°0.40 × 0.20 × 0.06 mm
V = 1769.11 (7) Å3
Data collection top
Bruker APEXII
diffractometer
4315 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.076
Graphite monochromatorθmax = 27.5°, θmin = 2.2°
ϕ and ω scansh = 1212
33681 measured reflectionsk = 1616
8126 independent reflectionsl = 2020
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)] = 0.052Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.147H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.0637P)2 + 0.0087P]
where P = (Fo2 + 2Fc2)/3
8126 reflections(Δ/σ)max = 0.001
433 parametersΔρmax = 0.21 e Å3
0 restraintsΔρmin = 0.22 e Å3
Crystal data top
C38H46N8O2γ = 92.935 (2)°
Mr = 646.83V = 1769.11 (7) Å3
Triclinic, P1Z = 2
a = 9.4269 (2) ÅMo Kα radiation
b = 12.3304 (3) ŵ = 0.08 mm1
c = 15.5500 (4) ÅT = 193 K
α = 101.121 (2)°0.40 × 0.20 × 0.06 mm
β = 92.175 (2)°
Data collection top
Bruker APEXII
diffractometer
4315 reflections with I > 2σ(I)
33681 measured reflectionsRint = 0.076
8126 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0520 restraints
wR(F2) = 0.147H-atom parameters constrained
S = 1.00Δρmax = 0.21 e Å3
8126 reflectionsΔρmin = 0.22 e Å3
433 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.49525 (16)1.12343 (12)0.23925 (10)0.0408 (4)
O20.51737 (15)0.90533 (11)0.37285 (9)0.0367 (4)
N10.27355 (18)1.11470 (12)0.29224 (11)0.0297 (4)
N20.28200 (18)0.93241 (13)0.38543 (11)0.0290 (4)
N30.3838 (2)0.70440 (15)0.17514 (14)0.0477 (5)
N40.4145 (2)0.60090 (15)0.17564 (15)0.0535 (6)
N50.5564 (2)0.60077 (14)0.18490 (13)0.0429 (5)
N61.0314 (2)0.65890 (16)0.19426 (15)0.0516 (6)
N70.9694 (2)0.73485 (17)0.16605 (13)0.0433 (5)
N80.9271 (2)0.81025 (18)0.14108 (15)0.0553 (6)
C10.1478 (2)1.05032 (15)0.30484 (13)0.0283 (5)
C20.0170 (2)1.07803 (17)0.27332 (14)0.0353 (5)
H20.01391.13620.24130.042*
C30.1078 (2)1.02300 (18)0.28764 (15)0.0405 (6)
H30.19601.04320.26570.049*
C40.1046 (2)0.93793 (18)0.33418 (15)0.0377 (5)
H40.19060.90030.34490.045*
C50.0246 (2)0.90793 (17)0.36500 (14)0.0340 (5)
H50.02670.84900.39630.041*
C60.1516 (2)0.96343 (15)0.35062 (13)0.0278 (5)
C70.3922 (2)1.06848 (16)0.25614 (13)0.0297 (5)
C80.3893 (2)0.94297 (15)0.24558 (13)0.0271 (5)
H80.29520.90990.21830.033*
C90.4037 (2)0.92453 (15)0.33936 (13)0.0288 (5)
C100.2720 (2)1.23642 (15)0.31792 (14)0.0345 (5)
H10A0.20541.26410.27750.041*
H10B0.36821.27000.31260.041*
C110.2275 (2)1.27102 (15)0.41053 (14)0.0286 (5)
C120.1029 (2)1.32471 (17)0.42944 (15)0.0364 (5)
H120.04351.33950.38280.044*
C130.0643 (3)1.35682 (18)0.51513 (17)0.0452 (6)
H130.02121.39330.52710.054*
C140.1498 (3)1.33594 (18)0.58312 (16)0.0459 (6)
H140.12361.35840.64200.055*
C150.2740 (3)1.28227 (18)0.56568 (15)0.0415 (6)
H150.33321.26780.61250.050*
C160.3115 (2)1.24989 (16)0.48007 (14)0.0343 (5)
H160.39641.21240.46840.041*
C170.2891 (2)0.91041 (17)0.47532 (13)0.0333 (5)
H17A0.20300.93740.50500.040*
H17B0.37230.95380.50790.040*
C180.3006 (2)0.78970 (17)0.48126 (14)0.0310 (5)
C190.3054 (2)0.70492 (17)0.40862 (15)0.0379 (5)
H190.29730.72070.35130.046*
C200.3221 (2)0.59694 (18)0.41938 (17)0.0451 (6)
H200.32640.53980.36910.054*
C210.3323 (2)0.5715 (2)0.50144 (19)0.0496 (7)
H210.34340.49740.50820.060*
C220.3262 (3)0.6553 (2)0.57389 (18)0.0522 (7)
H220.33300.63870.63100.063*
C230.3104 (2)0.76358 (19)0.56407 (15)0.0415 (6)
H230.30610.82040.61460.050*
C240.5083 (2)0.89162 (16)0.19044 (14)0.0316 (5)
H24A0.49790.90810.13080.038*
H24B0.60120.92550.21700.038*
C250.5065 (2)0.76899 (17)0.18398 (14)0.0328 (5)
C260.6166 (2)0.70312 (17)0.19058 (15)0.0387 (6)
H260.71510.72500.19770.046*
C270.6233 (3)0.49812 (18)0.19414 (17)0.0509 (7)
H27A0.57700.46730.24100.061*
H27B0.72460.51630.21290.061*
C280.6142 (3)0.41098 (18)0.11141 (16)0.0466 (6)
H28A0.66230.44010.06440.056*
H28B0.51320.39200.09200.056*
C290.6850 (3)0.30673 (17)0.12757 (16)0.0422 (6)
H29A0.78680.32620.14420.051*
H29B0.64070.28170.17770.051*
C300.6733 (3)0.21180 (17)0.04916 (16)0.0454 (6)
H30A0.71850.23600.00090.054*
H30B0.57160.19210.03220.054*
C310.7439 (3)0.10941 (17)0.06794 (15)0.0427 (6)
H31A0.84590.12930.08390.051*
H31B0.70030.08700.11930.051*
C320.7317 (3)0.01086 (17)0.00845 (15)0.0430 (6)
H32A0.62990.00720.02600.052*
H32B0.77890.03220.05900.052*
C330.7970 (3)0.09223 (17)0.01205 (15)0.0430 (6)
H33A0.89740.07330.03300.052*
H33B0.74570.11670.06000.052*
C340.7915 (3)0.18720 (17)0.06687 (15)0.0429 (6)
H34A0.69120.20440.08830.051*
H34B0.84380.16240.11430.051*
C350.8535 (3)0.29282 (17)0.04934 (15)0.0455 (6)
H35A0.79370.32360.00770.055*
H35B0.94990.27450.02120.055*
C360.8626 (3)0.38058 (17)0.13207 (15)0.0397 (6)
H36A0.91950.34860.17430.048*
H36B0.76560.40010.15910.048*
C370.9285 (3)0.48615 (17)0.11688 (15)0.0396 (6)
H37A1.02270.46710.08580.048*
H37C0.86710.52290.07940.048*
C380.9452 (3)0.56462 (18)0.20306 (15)0.0432 (6)
H38C0.84970.59350.22870.052*
H38A0.99030.52300.24430.052*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0375 (10)0.0340 (8)0.0512 (10)0.0034 (7)0.0123 (8)0.0086 (7)
O20.0314 (9)0.0370 (8)0.0403 (9)0.0042 (7)0.0061 (7)0.0049 (7)
N10.0317 (10)0.0210 (8)0.0362 (11)0.0022 (7)0.0042 (8)0.0046 (7)
N20.0294 (10)0.0297 (9)0.0279 (10)0.0015 (7)0.0025 (8)0.0058 (7)
N30.0338 (12)0.0308 (11)0.0760 (16)0.0051 (9)0.0020 (10)0.0035 (10)
N40.0373 (13)0.0324 (11)0.0869 (17)0.0053 (9)0.0011 (11)0.0018 (10)
N50.0375 (12)0.0319 (10)0.0561 (13)0.0098 (9)0.0019 (10)0.0004 (9)
N60.0459 (13)0.0370 (12)0.0724 (16)0.0090 (10)0.0151 (11)0.0079 (11)
N70.0390 (13)0.0407 (12)0.0462 (13)0.0067 (10)0.0021 (10)0.0016 (10)
N80.0532 (15)0.0488 (13)0.0639 (15)0.0019 (11)0.0071 (11)0.0134 (11)
C10.0290 (12)0.0226 (10)0.0312 (12)0.0031 (8)0.0027 (9)0.0007 (8)
C20.0334 (13)0.0345 (12)0.0388 (13)0.0066 (10)0.0002 (10)0.0082 (10)
C30.0308 (14)0.0428 (13)0.0454 (15)0.0072 (10)0.0023 (11)0.0020 (11)
C40.0291 (13)0.0388 (13)0.0420 (14)0.0026 (10)0.0064 (10)0.0002 (10)
C50.0356 (14)0.0301 (11)0.0347 (13)0.0006 (9)0.0066 (10)0.0019 (9)
C60.0282 (12)0.0244 (10)0.0293 (12)0.0022 (8)0.0020 (9)0.0010 (8)
C70.0319 (13)0.0284 (11)0.0284 (12)0.0036 (9)0.0002 (9)0.0043 (9)
C80.0236 (11)0.0269 (10)0.0301 (12)0.0023 (8)0.0027 (9)0.0030 (9)
C90.0302 (13)0.0215 (10)0.0331 (12)0.0002 (8)0.0015 (10)0.0026 (9)
C100.0425 (14)0.0226 (10)0.0387 (13)0.0029 (9)0.0039 (10)0.0059 (9)
C110.0291 (12)0.0207 (10)0.0367 (13)0.0002 (8)0.0043 (9)0.0072 (9)
C120.0300 (13)0.0332 (12)0.0460 (15)0.0038 (9)0.0025 (11)0.0077 (10)
C130.0353 (14)0.0388 (13)0.0604 (18)0.0075 (10)0.0163 (12)0.0031 (12)
C140.0559 (17)0.0396 (13)0.0404 (15)0.0048 (12)0.0168 (13)0.0029 (11)
C150.0476 (16)0.0424 (13)0.0364 (14)0.0009 (11)0.0015 (11)0.0131 (11)
C160.0323 (13)0.0308 (11)0.0419 (14)0.0044 (9)0.0057 (10)0.0106 (10)
C170.0354 (13)0.0372 (12)0.0265 (12)0.0018 (9)0.0000 (9)0.0045 (9)
C180.0228 (12)0.0360 (12)0.0357 (13)0.0000 (9)0.0001 (9)0.0117 (10)
C190.0408 (14)0.0341 (12)0.0395 (14)0.0008 (10)0.0002 (11)0.0093 (10)
C200.0427 (15)0.0311 (12)0.0605 (17)0.0018 (10)0.0032 (12)0.0067 (11)
C210.0360 (15)0.0412 (14)0.078 (2)0.0028 (11)0.0024 (13)0.0271 (14)
C220.0406 (16)0.0661 (18)0.0603 (18)0.0024 (13)0.0007 (13)0.0395 (15)
C230.0370 (14)0.0509 (14)0.0382 (14)0.0025 (11)0.0023 (11)0.0128 (11)
C240.0283 (12)0.0338 (11)0.0325 (12)0.0041 (9)0.0039 (9)0.0046 (9)
C250.0307 (13)0.0334 (12)0.0330 (12)0.0048 (9)0.0039 (10)0.0018 (9)
C260.0319 (13)0.0351 (13)0.0467 (14)0.0046 (10)0.0015 (11)0.0016 (10)
C270.0567 (18)0.0363 (13)0.0586 (17)0.0159 (12)0.0042 (13)0.0041 (12)
C280.0526 (17)0.0350 (13)0.0517 (16)0.0109 (11)0.0081 (12)0.0042 (11)
C290.0463 (15)0.0317 (12)0.0494 (15)0.0081 (10)0.0062 (12)0.0075 (11)
C300.0521 (16)0.0359 (13)0.0498 (16)0.0127 (11)0.0081 (12)0.0085 (11)
C310.0536 (16)0.0342 (12)0.0422 (14)0.0107 (11)0.0082 (12)0.0084 (11)
C320.0515 (16)0.0370 (13)0.0417 (14)0.0115 (11)0.0071 (11)0.0074 (10)
C330.0567 (17)0.0371 (13)0.0372 (14)0.0157 (11)0.0109 (12)0.0069 (10)
C340.0496 (16)0.0363 (13)0.0430 (14)0.0116 (11)0.0051 (11)0.0053 (10)
C350.0618 (18)0.0374 (13)0.0383 (14)0.0141 (12)0.0077 (12)0.0058 (11)
C360.0437 (15)0.0357 (12)0.0395 (14)0.0092 (10)0.0010 (11)0.0055 (10)
C370.0441 (15)0.0353 (12)0.0379 (14)0.0073 (10)0.0031 (11)0.0032 (10)
C380.0453 (15)0.0370 (13)0.0462 (15)0.0101 (11)0.0056 (11)0.0030 (11)
Geometric parameters (Å, º) top
O1—C71.222 (2)C19—C201.389 (3)
O2—C91.228 (2)C19—H190.9500
N1—C71.371 (3)C20—C211.373 (3)
N1—C11.434 (3)C20—H200.9500
N1—C101.478 (2)C21—C221.379 (3)
N2—C91.373 (3)C21—H210.9500
N2—C61.424 (2)C22—C231.388 (3)
N2—C171.474 (2)C22—H220.9500
N3—N41.324 (2)C23—H230.9500
N3—C251.357 (3)C24—C251.495 (3)
N4—N51.340 (3)C24—H24A0.9900
N5—C261.342 (3)C24—H24B0.9900
N5—C271.471 (3)C25—C261.363 (3)
N6—N71.238 (3)C26—H260.9500
N6—C381.477 (3)C27—C281.505 (3)
N7—N81.135 (3)C27—H27A0.9900
C1—C21.393 (3)C27—H27B0.9900
C1—C61.397 (3)C28—C291.536 (3)
C2—C31.375 (3)C28—H28A0.9900
C2—H20.9500C28—H28B0.9900
C3—C41.385 (3)C29—C301.515 (3)
C3—H30.9500C29—H29A0.9900
C4—C51.385 (3)C29—H29B0.9900
C4—H40.9500C30—C311.528 (3)
C5—C61.395 (3)C30—H30A0.9900
C5—H50.9500C30—H30B0.9900
C7—C81.523 (3)C31—C321.523 (3)
C8—C91.521 (3)C31—H31A0.9900
C8—C241.527 (3)C31—H31B0.9900
C8—H81.0000C32—C331.523 (3)
C10—C111.503 (3)C32—H32A0.9900
C10—H10A0.9900C32—H32B0.9900
C10—H10B0.9900C33—C341.521 (3)
C11—C161.389 (3)C33—H33A0.9900
C11—C121.392 (3)C33—H33B0.9900
C12—C131.383 (3)C34—C351.521 (3)
C12—H120.9500C34—H34A0.9900
C13—C141.377 (3)C34—H34B0.9900
C13—H130.9500C35—C361.521 (3)
C14—C151.384 (3)C35—H35A0.9900
C14—H140.9500C35—H35B0.9900
C15—C161.379 (3)C36—C371.525 (3)
C15—H150.9500C36—H36A0.9900
C16—H160.9500C36—H36B0.9900
C17—C181.518 (3)C37—C381.513 (3)
C17—H17A0.9900C37—H37A0.9900
C17—H17B0.9900C37—H37C0.9900
C18—C191.387 (3)C38—H38C0.9900
C18—C231.387 (3)C38—H38A0.9900
C7—N1—C1123.00 (16)C18—C23—C22120.7 (2)
C7—N1—C10119.34 (17)C18—C23—H23119.7
C1—N1—C10117.65 (16)C22—C23—H23119.7
C9—N2—C6122.66 (17)C25—C24—C8111.90 (17)
C9—N2—C17118.05 (17)C25—C24—H24A109.2
C6—N2—C17119.26 (17)C8—C24—H24A109.2
N4—N3—C25109.03 (18)C25—C24—H24B109.2
N3—N4—N5106.74 (18)C8—C24—H24B109.2
N4—N5—C26110.86 (17)H24A—C24—H24B107.9
N4—N5—C27119.71 (19)N3—C25—C26107.91 (19)
C26—N5—C27129.2 (2)N3—C25—C24122.42 (18)
N7—N6—C38115.6 (2)C26—C25—C24129.6 (2)
N8—N7—N6172.0 (2)N5—C26—C25105.5 (2)
C2—C1—C6118.94 (19)N5—C26—H26127.3
C2—C1—N1118.89 (18)C25—C26—H26127.3
C6—C1—N1122.12 (18)N5—C27—C28113.9 (2)
C3—C2—C1121.4 (2)N5—C27—H27A108.8
C3—C2—H2119.3C28—C27—H27A108.8
C1—C2—H2119.3N5—C27—H27B108.8
C2—C3—C4119.8 (2)C28—C27—H27B108.8
C2—C3—H3120.1H27A—C27—H27B107.7
C4—C3—H3120.1C27—C28—C29110.2 (2)
C5—C4—C3119.8 (2)C27—C28—H28A109.6
C5—C4—H4120.1C29—C28—H28A109.6
C3—C4—H4120.1C27—C28—H28B109.6
C4—C5—C6120.7 (2)C29—C28—H28B109.6
C4—C5—H5119.7H28A—C28—H28B108.1
C6—C5—H5119.7C30—C29—C28113.9 (2)
C5—C6—C1119.40 (19)C30—C29—H29A108.8
C5—C6—N2119.14 (18)C28—C29—H29A108.8
C1—C6—N2121.43 (18)C30—C29—H29B108.8
O1—C7—N1123.06 (18)C28—C29—H29B108.8
O1—C7—C8122.69 (19)H29A—C29—H29B107.7
N1—C7—C8114.09 (17)C29—C30—C31112.4 (2)
C9—C8—C7103.72 (15)C29—C30—H30A109.1
C9—C8—C24111.59 (16)C31—C30—H30A109.1
C7—C8—C24112.98 (17)C29—C30—H30B109.1
C9—C8—H8109.5C31—C30—H30B109.1
C7—C8—H8109.5H30A—C30—H30B107.9
C24—C8—H8109.5C32—C31—C30114.22 (19)
O2—C9—N2121.56 (19)C32—C31—H31A108.7
O2—C9—C8122.38 (19)C30—C31—H31A108.7
N2—C9—C8116.06 (17)C32—C31—H31B108.7
N1—C10—C11111.42 (16)C30—C31—H31B108.7
N1—C10—H10A109.3H31A—C31—H31B107.6
C11—C10—H10A109.3C33—C32—C31113.88 (19)
N1—C10—H10B109.3C33—C32—H32A108.8
C11—C10—H10B109.3C31—C32—H32A108.8
H10A—C10—H10B108.0C33—C32—H32B108.8
C16—C11—C12118.1 (2)C31—C32—H32B108.8
C16—C11—C10120.15 (19)H32A—C32—H32B107.7
C12—C11—C10121.70 (19)C34—C33—C32112.85 (19)
C13—C12—C11120.9 (2)C34—C33—H33A109.0
C13—C12—H12119.6C32—C33—H33A109.0
C11—C12—H12119.6C34—C33—H33B109.0
C14—C13—C12120.0 (2)C32—C33—H33B109.0
C14—C13—H13120.0H33A—C33—H33B107.8
C12—C13—H13120.0C35—C34—C33114.86 (19)
C13—C14—C15120.0 (2)C35—C34—H34A108.6
C13—C14—H14120.0C33—C34—H34A108.6
C15—C14—H14120.0C35—C34—H34B108.6
C16—C15—C14119.7 (2)C33—C34—H34B108.6
C16—C15—H15120.1H34A—C34—H34B107.5
C14—C15—H15120.1C34—C35—C36113.11 (19)
C15—C16—C11121.2 (2)C34—C35—H35A109.0
C15—C16—H16119.4C36—C35—H35A109.0
C11—C16—H16119.4C34—C35—H35B109.0
N2—C17—C18115.03 (17)C36—C35—H35B109.0
N2—C17—H17A108.5H35A—C35—H35B107.8
C18—C17—H17A108.5C35—C36—C37114.29 (18)
N2—C17—H17B108.5C35—C36—H36A108.7
C18—C17—H17B108.5C37—C36—H36A108.7
H17A—C17—H17B107.5C35—C36—H36B108.7
C19—C18—C23118.4 (2)C37—C36—H36B108.7
C19—C18—C17123.59 (19)H36A—C36—H36B107.6
C23—C18—C17117.94 (19)C38—C37—C36110.81 (18)
C18—C19—C20120.3 (2)C38—C37—H37A109.5
C18—C19—H19119.9C36—C37—H37A109.5
C20—C19—H19119.9C38—C37—H37C109.5
C21—C20—C19121.1 (2)C36—C37—H37C109.5
C21—C20—H20119.5H37A—C37—H37C108.1
C19—C20—H20119.5N6—C38—C37113.33 (19)
C20—C21—C22118.9 (2)N6—C38—H38C108.9
C20—C21—H21120.6C37—C38—H38C108.9
C22—C21—H21120.6N6—C38—H38A108.9
C21—C22—C23120.6 (2)C37—C38—H38A108.9
C21—C22—H22119.7H38C—C38—H38A107.7
C23—C22—H22119.7
C25—N3—N4—N50.1 (3)C10—C11—C12—C13179.42 (19)
N3—N4—N5—C260.2 (3)C11—C12—C13—C140.1 (3)
N3—N4—N5—C27175.6 (2)C12—C13—C14—C150.4 (3)
C7—N1—C1—C2128.6 (2)C13—C14—C15—C160.0 (3)
C10—N1—C1—C250.0 (2)C14—C15—C16—C110.6 (3)
C7—N1—C1—C653.9 (3)C12—C11—C16—C150.8 (3)
C10—N1—C1—C6127.5 (2)C10—C11—C16—C15179.04 (19)
C6—C1—C2—C31.1 (3)C9—N2—C17—C1872.5 (2)
N1—C1—C2—C3176.48 (19)C6—N2—C17—C18109.0 (2)
C1—C2—C3—C40.1 (3)N2—C17—C18—C190.5 (3)
C2—C3—C4—C50.8 (3)N2—C17—C18—C23178.86 (18)
C3—C4—C5—C60.8 (3)C23—C18—C19—C201.1 (3)
C4—C5—C6—C10.2 (3)C17—C18—C19—C20177.3 (2)
C4—C5—C6—N2178.23 (18)C18—C19—C20—C210.8 (3)
C2—C1—C6—C51.1 (3)C19—C20—C21—C220.2 (4)
N1—C1—C6—C5176.37 (18)C20—C21—C22—C230.2 (4)
C2—C1—C6—N2179.11 (18)C19—C18—C23—C220.8 (3)
N1—C1—C6—N21.6 (3)C17—C18—C23—C22177.7 (2)
C9—N2—C6—C5138.91 (19)C21—C22—C23—C180.1 (4)
C17—N2—C6—C542.7 (2)C9—C8—C24—C2561.4 (2)
C9—N2—C6—C143.1 (3)C7—C8—C24—C25177.80 (17)
C17—N2—C6—C1135.30 (19)N4—N3—C25—C260.3 (3)
C1—N1—C7—O1174.29 (19)N4—N3—C25—C24176.8 (2)
C10—N1—C7—O14.3 (3)C8—C24—C25—N339.0 (3)
C1—N1—C7—C810.3 (3)C8—C24—C25—C26136.7 (2)
C10—N1—C7—C8171.12 (17)N4—N5—C26—C250.4 (3)
O1—C7—C8—C9105.9 (2)C27—N5—C26—C25175.3 (2)
N1—C7—C8—C969.6 (2)N3—C25—C26—N50.4 (2)
O1—C7—C8—C2415.1 (3)C24—C25—C26—N5176.6 (2)
N1—C7—C8—C24169.45 (17)N4—N5—C27—C2870.5 (3)
C6—N2—C9—O2174.76 (17)C26—N5—C27—C28115.0 (3)
C17—N2—C9—O23.7 (3)N5—C27—C28—C29179.3 (2)
C6—N2—C9—C84.2 (3)C27—C28—C29—C30176.6 (2)
C17—N2—C9—C8177.39 (16)C28—C29—C30—C31179.6 (2)
C7—C8—C9—O299.5 (2)C29—C30—C31—C32178.6 (2)
C24—C8—C9—O222.4 (3)C30—C31—C32—C33177.6 (2)
C7—C8—C9—N279.4 (2)C31—C32—C33—C34176.5 (2)
C24—C8—C9—N2158.65 (16)C32—C33—C34—C35179.1 (2)
C7—N1—C10—C11129.1 (2)C33—C34—C35—C36172.9 (2)
C1—N1—C10—C1152.3 (2)C34—C35—C36—C37178.2 (2)
N1—C10—C11—C1664.5 (2)C35—C36—C37—C38175.1 (2)
N1—C10—C11—C12115.7 (2)N7—N6—C38—C3778.5 (3)
C16—C11—C12—C130.5 (3)C36—C37—C38—N6169.6 (2)

Experimental details

Crystal data
Chemical formulaC38H46N8O2
Mr646.83
Crystal system, space groupTriclinic, P1
Temperature (K)193
a, b, c (Å)9.4269 (2), 12.3304 (3), 15.5500 (4)
α, β, γ (°)101.121 (2), 92.175 (2), 92.935 (2)
V3)1769.11 (7)
Z2
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.40 × 0.20 × 0.06
Data collection
DiffractometerBruker APEXII
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
33681, 8126, 4315
Rint0.076
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.052, 0.147, 1.00
No. of reflections8126
No. of parameters433
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.21, 0.22

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

 

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
First citationBruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
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
First citationJabli, H., Kandri Rodi, Y., Ladeira, S., Essassi, E. M. & Ng, S. W. (2010). Acta Cryst. E66, o126.  Web of Science CSD CrossRef IUCr Journals
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationWestrip, S. P. (2010). publCIF. In preparation.

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