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Acta Crystallogr Sect E Struct Rep Online. 2010 January 1; 66(Pt 1): o231.
Published online 2009 December 24. doi:  10.1107/S1600536809054476
PMCID: PMC2980118

4-[(1,5-Dibenzyl-2,4-dioxo-2,3,4,5-tetra­hydro-1H-1,5-benzodiazepin-3-yl)meth­yl]-1-n-octyl-1H-1,2,3-triazole

Abstract

The reaction of 1,5-dibenzyl-3-propargyl-1,5-benzodiazepine-2,4-dione with 1-azido-n-octane in the presence of catalysts leads to the formation of the title compound, C34H39N5O2, which features a phenyl­ene ring fused with a seven-membered diazepinyl ring. The latter ring adopts a boat conformation with the octyltriazolylmethyl-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 homologues, see: Jabli et al. (2009 [triangle], 2010 [triangle]).

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Object name is e-66-0o231-scheme1.jpg

Experimental

Crystal data

  • C34H39N5O2
  • M r = 549.70
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-66-0o231-efi1.jpg
  • a = 9.1797 (2) Å
  • b = 10.4238 (2) Å
  • c = 31.4716 (7) Å
  • V = 3011.4 (1) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.08 mm−1
  • T = 193 K
  • 0.30 × 0.16 × 0.10 mm

Data collection

  • Bruker APEXII diffractometer
  • 44767 measured reflections
  • 3027 independent reflections
  • 2307 reflections with I > 2σ(I)
  • R int = 0.072

Refinement

  • R[F 2 > 2σ(F 2)] = 0.057
  • wR(F 2) = 0.174
  • S = 1.02
  • 3027 reflections
  • 370 parameters
  • 59 restraints
  • H-atom parameters constrained
  • Δρmax = 0.59 e Å−3
  • Δρmin = −0.41 e Å−3

Data collection: APEX2 (Bruker, 2005 [triangle]); cell refinement: SAINT (Bruker, 2005 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2010 [triangle]).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809054476/bt5142sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809054476/bt5142Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

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

supplementary crystallographic information

Experimental

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-azido-n-octane (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

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).

For the octyl chain, the 1,2-related carbon-carbon distances were restrained to 1.54±0.01 Å and the 1,3-related ones to 2.51±0.01 Å. The anisotropic displacement ellipsoids were restrained to be nearly isotropic.

Figures

Fig. 1.
Anisotropic displacement ellipsoid plot (Barbour, 2001) of C34H23N5O2 at the 70% probability level; hydrogen atoms are drawn as arbitrary radius.

Crystal data

C34H39N5O2F(000) = 1176
Mr = 549.70Dx = 1.212 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 5123 reflections
a = 9.1797 (2) Åθ = 2.3–19.1°
b = 10.4238 (2) ŵ = 0.08 mm1
c = 31.4716 (7) ÅT = 193 K
V = 3011.4 (1) Å3Block, colorless
Z = 40.30 × 0.16 × 0.10 mm

Data collection

Bruker APEXII diffractometer2307 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.072
graphiteθmax = 25.0°, θmin = 1.3°
[var phi] and ω scansh = −10→10
44767 measured reflectionsk = −11→12
3027 independent reflectionsl = −37→37

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.057H-atom parameters constrained
wR(F2) = 0.174w = 1/[σ2(Fo2) + (0.1036P)2 + 1.5833P] where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max = 0.001
3027 reflectionsΔρmax = 0.59 e Å3
370 parametersΔρmin = −0.40 e Å3
59 restraintsAbsolute structure: Friedel pairs were merged
Primary atom site location: structure-invariant direct methods

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

xyzUiso*/Ueq
O10.6191 (3)0.4931 (3)0.14072 (10)0.0418 (8)
O20.6411 (3)0.6919 (4)0.04134 (9)0.0449 (8)
N10.8576 (4)0.4659 (3)0.12497 (11)0.0316 (8)
N20.8703 (4)0.6098 (3)0.04556 (11)0.0312 (8)
N30.7316 (5)0.8647 (5)0.18835 (15)0.0663 (14)
N40.7049 (5)0.8835 (5)0.22909 (16)0.0658 (15)
N50.5823 (5)0.8206 (4)0.23825 (13)0.0453 (10)
C10.9921 (5)0.5125 (4)0.10829 (13)0.0306 (10)
C21.1212 (5)0.4862 (5)0.12995 (15)0.0383 (11)
H21.11780.44080.15610.046*
C31.2544 (5)0.5254 (5)0.11379 (16)0.0434 (12)
H31.34150.50620.12880.052*
C41.2608 (5)0.5919 (5)0.07613 (16)0.0432 (12)
H41.35240.61760.06500.052*
C51.1341 (5)0.6214 (4)0.05445 (14)0.0356 (10)
H51.13930.66890.02870.043*
C60.9983 (5)0.5823 (4)0.06998 (13)0.0295 (10)
C70.7468 (5)0.6614 (4)0.06302 (13)0.0323 (10)
C80.7454 (5)0.6736 (4)0.11111 (13)0.0327 (10)
H80.83950.71170.12090.039*
C90.7325 (5)0.5370 (4)0.12750 (13)0.0312 (10)
C100.8521 (5)0.3333 (4)0.14053 (13)0.0355 (10)
H10A0.93230.28460.12700.043*
H10B0.75930.29440.13100.043*
C110.8638 (5)0.3163 (4)0.18838 (13)0.0325 (9)
C120.8477 (5)0.1925 (5)0.20461 (14)0.0386 (11)
H120.82930.12280.18590.046*
C130.8583 (6)0.1711 (5)0.24805 (16)0.0488 (13)
H130.84540.08690.25900.059*
C140.8876 (6)0.2714 (6)0.27544 (17)0.0535 (14)
H140.89570.25670.30510.064*
C150.9048 (6)0.3930 (6)0.25920 (16)0.0522 (14)
H150.92620.46220.27790.063*
C160.8913 (5)0.4160 (5)0.21615 (14)0.0411 (11)
H160.90100.50100.20560.049*
C170.8803 (5)0.6010 (4)−0.00113 (12)0.0335 (10)
H17A0.95580.6615−0.01120.040*
H17B0.78610.6278−0.01360.040*
C180.9170 (5)0.4679 (5)−0.01692 (14)0.0358 (10)
C190.8245 (6)0.3651 (5)−0.00935 (19)0.0567 (15)
H190.74070.37720.00790.068*
C200.8518 (8)0.2465 (6)−0.0263 (2)0.078 (2)
H200.78720.1770−0.02110.093*
C210.9754 (8)0.2290 (6)−0.0514 (2)0.0731 (19)
H210.99460.1477−0.06380.088*
C221.0674 (7)0.3274 (7)−0.05782 (19)0.0701 (18)
H221.15290.3146−0.07430.084*
C231.0392 (6)0.4459 (6)−0.04097 (15)0.0476 (13)
H231.10550.5142−0.04600.057*
C240.6185 (5)0.7586 (5)0.12581 (14)0.0420 (11)
H24A0.61940.83940.10920.050*
H24B0.52550.71410.11980.050*
C250.6250 (5)0.7901 (4)0.17170 (14)0.0381 (11)
C260.5306 (5)0.7603 (5)0.20384 (15)0.0438 (12)
H260.44620.70790.20210.053*
C270.5207 (7)0.8285 (6)0.28125 (16)0.0652 (16)
H27A0.41890.79730.28030.078*
H27B0.51810.91980.29000.078*
C280.6026 (10)0.7531 (7)0.3147 (2)0.104 (3)
H28A0.70030.79190.31820.125*
H28B0.55070.76250.34210.125*
C290.6209 (9)0.6171 (6)0.3060 (2)0.099 (2)
H29A0.69330.60650.28300.119*
H29B0.52710.58170.29580.119*
C300.6720 (7)0.5384 (6)0.3458 (2)0.0790 (19)
H30A0.59540.54410.36790.095*
H30B0.68070.44710.33750.095*
C310.8145 (6)0.5805 (6)0.36514 (19)0.0740 (19)
H31A0.79960.66300.38010.089*
H31B0.88610.59510.34210.089*
C320.8765 (7)0.4832 (7)0.39625 (19)0.0773 (19)
H32A0.90420.40450.38060.093*
H32B0.80040.45970.41720.093*
C331.0108 (7)0.5354 (8)0.4200 (2)0.088 (2)
H33A1.09270.54440.39980.105*
H33B0.98810.62160.43140.105*
C341.0553 (8)0.4517 (8)0.4550 (2)0.086 (2)
H34A1.14170.48760.46890.129*
H34B1.07820.36620.44380.129*
H34C0.97580.44500.47560.129*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0256 (16)0.055 (2)0.0451 (18)−0.0050 (16)0.0030 (14)0.0068 (15)
O20.0338 (17)0.066 (2)0.0345 (16)0.0123 (18)−0.0067 (15)0.0071 (16)
N10.0299 (19)0.0324 (19)0.0325 (18)0.0024 (17)0.0018 (16)0.0069 (16)
N20.0281 (18)0.038 (2)0.0270 (18)0.0016 (18)−0.0004 (16)0.0033 (15)
N30.061 (3)0.084 (4)0.054 (3)−0.025 (3)0.014 (2)−0.012 (3)
N40.058 (3)0.078 (4)0.062 (3)−0.026 (3)0.011 (2)−0.026 (3)
N50.039 (2)0.054 (3)0.043 (2)0.005 (2)0.0033 (18)−0.009 (2)
C10.027 (2)0.034 (2)0.031 (2)0.003 (2)0.0016 (18)0.0002 (19)
C20.032 (2)0.044 (3)0.039 (2)0.007 (2)−0.003 (2)0.005 (2)
C30.029 (2)0.050 (3)0.051 (3)0.007 (2)−0.003 (2)0.002 (3)
C40.028 (2)0.050 (3)0.052 (3)0.000 (2)0.007 (2)0.000 (3)
C50.028 (2)0.039 (2)0.039 (2)−0.002 (2)0.002 (2)0.002 (2)
C60.026 (2)0.032 (2)0.030 (2)0.004 (2)0.0005 (18)−0.0012 (18)
C70.028 (2)0.038 (2)0.031 (2)0.003 (2)0.0000 (18)0.004 (2)
C80.025 (2)0.038 (2)0.035 (2)0.005 (2)0.0011 (18)0.000 (2)
C90.031 (2)0.039 (2)0.024 (2)0.003 (2)0.0012 (18)0.0041 (19)
C100.040 (2)0.031 (2)0.035 (2)−0.001 (2)−0.004 (2)0.0020 (19)
C110.025 (2)0.035 (2)0.037 (2)0.001 (2)0.0014 (19)0.0009 (19)
C120.041 (3)0.034 (2)0.041 (3)0.000 (2)0.002 (2)0.004 (2)
C130.044 (3)0.049 (3)0.053 (3)0.003 (3)−0.004 (2)0.020 (3)
C140.049 (3)0.072 (4)0.040 (3)−0.003 (3)−0.003 (2)0.012 (3)
C150.059 (3)0.059 (3)0.039 (3)−0.011 (3)−0.004 (2)−0.003 (2)
C160.044 (3)0.040 (3)0.039 (3)−0.007 (2)0.004 (2)0.002 (2)
C170.033 (2)0.040 (2)0.028 (2)0.002 (2)0.0015 (19)0.0038 (18)
C180.033 (2)0.042 (3)0.032 (2)−0.001 (2)−0.0010 (19)0.002 (2)
C190.053 (3)0.041 (3)0.076 (4)−0.004 (3)0.009 (3)0.000 (3)
C200.074 (4)0.047 (3)0.112 (6)−0.005 (4)−0.011 (4)−0.005 (4)
C210.078 (5)0.054 (4)0.088 (5)0.020 (4)−0.020 (4)−0.027 (3)
C220.062 (4)0.084 (5)0.064 (4)0.019 (4)0.008 (3)−0.023 (4)
C230.042 (3)0.057 (3)0.043 (3)0.006 (3)0.007 (2)−0.008 (3)
C240.032 (2)0.050 (3)0.044 (3)0.013 (2)−0.001 (2)−0.003 (2)
C250.027 (2)0.040 (3)0.047 (3)0.006 (2)0.004 (2)−0.005 (2)
C260.036 (3)0.052 (3)0.043 (3)−0.005 (2)0.004 (2)−0.005 (2)
C270.065 (3)0.087 (4)0.044 (3)0.000 (4)0.004 (3)−0.012 (3)
C280.113 (6)0.116 (6)0.083 (5)0.011 (5)0.017 (5)0.006 (5)
C290.082 (5)0.112 (6)0.103 (5)0.006 (5)−0.004 (4)−0.023 (5)
C300.071 (4)0.072 (4)0.094 (5)−0.003 (4)−0.002 (4)0.007 (4)
C310.076 (4)0.063 (4)0.083 (4)−0.018 (3)0.020 (3)−0.016 (3)
C320.070 (4)0.090 (4)0.072 (4)−0.017 (4)0.014 (3)−0.001 (3)
C330.078 (4)0.091 (5)0.093 (5)−0.015 (4)0.008 (4)0.013 (4)
C340.068 (4)0.091 (5)0.099 (5)−0.006 (4)0.001 (4)0.019 (4)

Geometric parameters (Å, °)

O1—C91.211 (5)C17—H17A0.9900
O2—C71.228 (5)C17—H17B0.9900
N1—C91.369 (6)C18—C231.373 (6)
N1—C11.426 (5)C18—C191.388 (7)
N1—C101.468 (6)C19—C201.369 (8)
N2—C71.370 (6)C19—H190.9500
N2—C61.433 (5)C20—C211.393 (10)
N2—C171.475 (5)C20—H200.9500
N3—N41.320 (6)C21—C221.344 (10)
N3—C251.356 (6)C21—H210.9500
N4—N51.334 (6)C22—C231.368 (9)
N5—C261.339 (6)C22—H220.9500
N5—C271.469 (6)C23—H230.9500
C1—C21.394 (6)C24—C251.482 (6)
C1—C61.409 (6)C24—H24A0.9900
C2—C31.386 (7)C24—H24B0.9900
C2—H20.9500C25—C261.367 (6)
C3—C41.374 (7)C26—H260.9500
C3—H30.9500C27—C281.513 (7)
C4—C51.384 (7)C27—H27A0.9900
C4—H40.9500C27—H27B0.9900
C5—C61.399 (6)C28—C291.453 (7)
C5—H50.9500C28—H28A0.9900
C7—C81.519 (6)C28—H28B0.9900
C8—C91.519 (6)C29—C301.569 (7)
C8—C241.535 (6)C29—H29A0.9900
C8—H81.0000C29—H29B0.9900
C10—C111.520 (6)C30—C311.508 (7)
C10—H10A0.9900C30—H30A0.9900
C10—H10B0.9900C30—H30B0.9900
C11—C161.382 (6)C31—C321.520 (7)
C11—C121.395 (6)C31—H31A0.9900
C12—C131.389 (6)C31—H31B0.9900
C12—H120.9500C32—C331.541 (7)
C13—C141.382 (8)C32—H32A0.9900
C13—H130.9500C32—H32B0.9900
C14—C151.376 (8)C33—C341.462 (9)
C14—H140.9500C33—H33A0.9900
C15—C161.382 (7)C33—H33B0.9900
C15—H150.9500C34—H34A0.9800
C16—H160.9500C34—H34B0.9800
C17—C181.512 (6)C34—H34C0.9800
C9—N1—C1124.2 (3)C20—C19—H19119.4
C9—N1—C10117.5 (4)C18—C19—H19119.4
C1—N1—C10118.3 (4)C19—C20—C21119.2 (6)
C7—N2—C6122.8 (3)C19—C20—H20120.4
C7—N2—C17118.4 (3)C21—C20—H20120.4
C6—N2—C17118.1 (3)C22—C21—C20119.8 (6)
N4—N3—C25109.0 (4)C22—C21—H21120.1
N3—N4—N5107.1 (4)C20—C21—H21120.1
N4—N5—C26110.8 (4)C21—C22—C23120.8 (6)
N4—N5—C27119.8 (5)C21—C22—H22119.6
C26—N5—C27129.4 (5)C23—C22—H22119.6
C2—C1—C6119.0 (4)C22—C23—C18121.3 (6)
C2—C1—N1119.2 (4)C22—C23—H23119.4
C6—C1—N1121.7 (4)C18—C23—H23119.4
C3—C2—C1120.8 (4)C25—C24—C8113.0 (4)
C3—C2—H2119.6C25—C24—H24A109.0
C1—C2—H2119.6C8—C24—H24A109.0
C4—C3—C2120.2 (5)C25—C24—H24B109.0
C4—C3—H3119.9C8—C24—H24B109.0
C2—C3—H3119.9H24A—C24—H24B107.8
C3—C4—C5120.1 (4)N3—C25—C26107.5 (4)
C3—C4—H4119.9N3—C25—C24122.2 (4)
C5—C4—H4119.9C26—C25—C24130.2 (4)
C4—C5—C6120.8 (4)N5—C26—C25105.5 (4)
C4—C5—H5119.6N5—C26—H26127.2
C6—C5—H5119.6C25—C26—H26127.2
C5—C6—C1119.0 (4)N5—C27—C28114.8 (5)
C5—C6—N2119.0 (4)N5—C27—H27A108.6
C1—C6—N2121.9 (4)C28—C27—H27A108.6
O2—C7—N2122.2 (4)N5—C27—H27B108.6
O2—C7—C8121.7 (4)C28—C27—H27B108.6
N2—C7—C8116.1 (4)H27A—C27—H27B107.5
C7—C8—C9105.1 (4)C29—C28—C27115.7 (6)
C7—C8—C24110.8 (4)C29—C28—H28A108.4
C9—C8—C24112.3 (4)C27—C28—H28A108.4
C7—C8—H8109.5C29—C28—H28B108.4
C9—C8—H8109.5C27—C28—H28B108.4
C24—C8—H8109.5H28A—C28—H28B107.4
O1—C9—N1122.4 (4)C28—C29—C30113.3 (6)
O1—C9—C8122.6 (4)C28—C29—H29A108.9
N1—C9—C8115.0 (4)C30—C29—H29A108.9
N1—C10—C11116.0 (4)C28—C29—H29B108.9
N1—C10—H10A108.3C30—C29—H29B108.9
C11—C10—H10A108.3H29A—C29—H29B107.7
N1—C10—H10B108.3C31—C30—C29115.4 (5)
C11—C10—H10B108.3C31—C30—H30A108.4
H10A—C10—H10B107.4C29—C30—H30A108.4
C16—C11—C12118.9 (4)C31—C30—H30B108.4
C16—C11—C10123.5 (4)C29—C30—H30B108.4
C12—C11—C10117.6 (4)H30A—C30—H30B107.5
C13—C12—C11120.1 (5)C30—C31—C32113.0 (5)
C13—C12—H12119.9C30—C31—H31A109.0
C11—C12—H12119.9C32—C31—H31A109.0
C14—C13—C12120.4 (5)C30—C31—H31B109.0
C14—C13—H13119.8C32—C31—H31B109.0
C12—C13—H13119.8H31A—C31—H31B107.8
C15—C14—C13119.2 (5)C31—C32—C33112.1 (5)
C15—C14—H14120.4C31—C32—H32A109.2
C13—C14—H14120.4C33—C32—H32A109.2
C14—C15—C16120.9 (5)C31—C32—H32B109.2
C14—C15—H15119.5C33—C32—H32B109.2
C16—C15—H15119.5H32A—C32—H32B107.9
C15—C16—C11120.4 (5)C34—C33—C32112.2 (6)
C15—C16—H16119.8C34—C33—H33A109.2
C11—C16—H16119.8C32—C33—H33A109.2
N2—C17—C18113.5 (3)C34—C33—H33B109.2
N2—C17—H17A108.9C32—C33—H33B109.2
C18—C17—H17A108.9H33A—C33—H33B107.9
N2—C17—H17B108.9C33—C34—H34A109.5
C18—C17—H17B108.9C33—C34—H34B109.5
H17A—C17—H17B107.7H34A—C34—H34B109.5
C23—C18—C19117.7 (5)C33—C34—H34C109.5
C23—C18—C17121.1 (4)H34A—C34—H34C109.5
C19—C18—C17121.1 (4)H34B—C34—H34C109.5
C20—C19—C18121.2 (6)
C25—N3—N4—N50.3 (7)N1—C10—C11—C16−5.8 (7)
N3—N4—N5—C260.7 (6)N1—C10—C11—C12175.1 (4)
N3—N4—N5—C27−177.2 (5)C16—C11—C12—C130.4 (7)
C9—N1—C1—C2135.7 (5)C10—C11—C12—C13179.5 (4)
C10—N1—C1—C2−44.3 (6)C11—C12—C13—C14−1.2 (8)
C9—N1—C1—C6−45.7 (6)C12—C13—C14—C150.6 (8)
C10—N1—C1—C6134.4 (4)C13—C14—C15—C160.9 (9)
C6—C1—C2—C3−1.3 (7)C14—C15—C16—C11−1.6 (8)
N1—C1—C2—C3177.3 (5)C12—C11—C16—C151.0 (7)
C1—C2—C3—C40.5 (8)C10—C11—C16—C15−178.1 (5)
C2—C3—C4—C50.8 (8)C7—N2—C17—C18−127.1 (4)
C3—C4—C5—C6−1.2 (7)C6—N2—C17—C1862.2 (5)
C4—C5—C6—C10.3 (7)N2—C17—C18—C23−121.0 (4)
C4—C5—C6—N2−177.2 (5)N2—C17—C18—C1962.2 (6)
C2—C1—C6—C51.0 (7)C23—C18—C19—C20−1.9 (8)
N1—C1—C6—C5−177.7 (4)C17—C18—C19—C20175.0 (5)
C2—C1—C6—N2178.4 (4)C18—C19—C20—C210.5 (10)
N1—C1—C6—N2−0.3 (7)C19—C20—C21—C221.3 (10)
C7—N2—C6—C5−132.9 (5)C20—C21—C22—C23−1.7 (10)
C17—N2—C6—C537.4 (6)C21—C22—C23—C180.2 (9)
C7—N2—C6—C149.7 (6)C19—C18—C23—C221.6 (8)
C17—N2—C6—C1−140.0 (4)C17—C18—C23—C22−175.3 (5)
C6—N2—C7—O2175.4 (4)C7—C8—C24—C25−171.2 (4)
C17—N2—C7—O25.1 (7)C9—C8—C24—C2571.6 (5)
C6—N2—C7—C8−7.1 (6)N4—N3—C25—C26−1.0 (7)
C17—N2—C7—C8−177.3 (4)N4—N3—C25—C24175.9 (5)
O2—C7—C8—C9106.5 (5)C8—C24—C25—N366.7 (6)
N2—C7—C8—C9−71.1 (5)C8—C24—C25—C26−117.1 (6)
O2—C7—C8—C24−15.0 (6)N4—N5—C26—C25−1.3 (6)
N2—C7—C8—C24167.4 (4)C27—N5—C26—C25176.3 (5)
C1—N1—C9—O1177.8 (4)N3—C25—C26—N51.4 (6)
C10—N1—C9—O1−2.3 (6)C24—C25—C26—N5−175.2 (5)
C1—N1—C9—C8−0.3 (6)N4—N5—C27—C28−73.6 (7)
C10—N1—C9—C8179.7 (3)C26—N5—C27—C28109.0 (7)
C7—C8—C9—O1−102.6 (5)N5—C27—C28—C29−56.3 (10)
C24—C8—C9—O117.9 (6)C27—C28—C29—C30−166.2 (6)
C7—C8—C9—N175.4 (5)C28—C29—C30—C31−58.8 (10)
C24—C8—C9—N1−164.0 (4)C29—C30—C31—C32−166.2 (6)
C9—N1—C10—C11−80.1 (5)C30—C31—C32—C33−172.4 (6)
C1—N1—C10—C1199.9 (5)C31—C32—C33—C34170.1 (6)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5142).

References

  • 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. [PMC free article] [PubMed]
  • Jabli, H., Kandri Rodi, Y., Ladeira, S., Essassi, E. M. & Ng, S. W. (2010). Acta Cryst. E66, o126. [PMC free article] [PubMed]
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Westrip, S. P. (2010). publCIF In preparation.

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