supplementary materials


Acta Cryst. (2010). E66, o232    [ doi:10.1107/S1600536809054464 ]

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

H. Jabli, F. Ouazzani Chahdi, N. Saffon, E. M. Essassi and S. W. Ng

Abstract top

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 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
graphiteθmax = 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
Rint = 0.076
33681 measured reflectionsθmax = 27.5°
8126 independent reflectionsStandard reflections: 0
4315 reflections with I > 2σ(I)
Refinement top
R[F2 > 2σ(F2)] = 0.052H-atom parameters constrained
wR(F2) = 0.147Δρmax = 0.21 e Å3
S = 1.00Δρmin = 0.22 e Å3
8126 reflectionsAbsolute structure: ?
433 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
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, °) 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)
Acknowledgements top

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

references
References top

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.

Bruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.

Jabli, H., Ouazzani Chahdi, F., Garrigues, B., Essassi, E. M. & Ng, S. W. (2009). Acta Cryst. E65, o3149.

Jabli, H., Kandri Rodi, Y., Ladeira, S., Essassi, E. M. & Ng, S. W. (2010). Acta Cryst. E66, o126.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Westrip, S. P. (2010). publCIF. In preparation.