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Acta Cryst. (2007). E63, o2800    [ doi:10.1107/S1600536807020764 ]

2,2',2'',2'''-[N,N,N',N'-(3,6-Dioxaoctane-1,8-diyldinitrilo)tetramethylene]tetrakis(benzimidazolium) tetranitrate

C.-S. Zhou, S. Hu and X.-G. Meng

Abstract top

The cation of the title compound, C38H44N10O24+·4NO3-, is centrosymmetric. In the crystal structure, cations and anions are linked into a three-dimensional framework by a combination of N-H...O and C-H...O hydrogen bonds and aromatic [pi]-[pi] stacking interactions.

Comment top

As part of our continuing studies on the ligands or metal complexes containing multi-benzimidazole groups (Zhang et al., 2005; Li et al., 2005; Qiu et al., 2005), we report here the crystal structure of a related compound, (I), which was obtained unexpectedly by reacting µ2-N,N, N', N'-tetrakis(Benzimidazol-2-ylmethyl)- 3,6- dioxaoctane-1,8-diamine (EGTB) with Fe(NO3).6H2O in H2O solution.

In the aymmetric unit of (I) (Fig. 1), the cation lies across an inversion center in space group of P21/c. The two terminal benzimidazoles rings on one side of the cation are effectively planar with the dihedral angle of only 0.75 (1)°.

All imine N atoms in the benzimidazole groups of are protonated foming a tetracation. Two nitrate anions lie to the inner side of the two end-on benzimidazole groups, forming the four nearly symmetric intra-molecular hydrogen bonds (Table 1). However, the other two anions lie at the outside of the two benzimidazole groups, linking the adjacent cations into a two-dimensional network running parallel the (100) direction. These networks are further joined by the C7–H···O7i (symmetry code as in Table 1) hydrogen bonds, forming a three-dimensional framework (Fig.2). In addition, the supramolecular aggregation is augmented by π-π stacking interactions between the aromatic rings C5—C10 and C13—C18, respectively. The two phenyl rings which lie in the molecules at (x,y,z) and (-x,1 - y,-z), respectively, are almost parallel with the dihedral angle of only 1.36 (1)°, the ring centroid separation of 3.682 (2) Å and the interpalanar spacing of ca 3.404 Å.

Related literature top

We have already published some crystal structures tha are related to the title compound (Zhang et al., 2005; Li et al., 2005; Qiu et al., 2005).

For related literature, see: Hendriks et al. (1982).

Experimental top

All reagents and solvents were used as obtained without further purification. EGTB [EGTB = (µ2-N,N,N',N'- tetrakis(Benzimidazol-2-ylmethyl)-3,6-dioxaoctane-1,8-diamine] was prepared according to literature procedure (Hendriks et al., 1982). The title organic salt was obtained unexpectedly by reacting EGTB with Fe(NO3).6H2O (molar ratio: 1/2). The mixture was stirred for half an hour at 70° and then filtered. The resulting pale-yellow solution was kept in air for one week. Crystals of (I) suitable for single-crystal X-ray diffraction analysis were grown by slow evaporation of the solution at the bottom of the vessel.

Refinement top

All H atoms bonded to carbon atoms were placed in calculated positions with C–H=0.97 Å(methylene) and 0.93 Å(aromatic), Uiso(H) = 1.2Ueq(C). H atoms bonded to imine N atoms were located from the difference maps and the N—H distance were refined freely without any constraints, but their Uiso(H) values were set 1.2 times Ueq of their carrier atoms.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON.

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. Hydrogen bonds are shown as dashed lines. Atoms marked with suffix 'a' are related by the symmetry operator (1 - x, 1 - y, 1 - z).
[Figure 2] Fig. 2. Part of the crystal structure of (I), showing the formation of the three-dimensional network. Hydrogen bonding are shown as dashed lines. For the sake of clarity, H atoms not involved in the motif have been omitted.
2,2',2'',2'''-[N,N,N',N'-(3,6-Dioxaoctane-1,8- diyldinitrilo)tetramethylene]tetrakis(benzimidazolium) tetranitrate top
Crystal data top
C38H44N10O24+·4(NO3−)F(000) = 964
Mr = 920.87Dx = 1.439 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2223 reflections
a = 8.4296 (6) Åθ = 2.4–19.9°
b = 17.6744 (12) ŵ = 0.11 mm−1
c = 14.279 (1) ÅT = 294 K
β = 92.421 (1)°Block, colourless
V = 2125.5 (3) Å30.20 × 0.12 × 0.10 mm
Z = 2
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer		4642 independent reflections
Radiation source: fine focus sealed Siemens Mo tube2655 reflections with I > 2σ(I)
graphiteRint = 0.067
0.3° wide ω exposures scansθmax = 27.0°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2001)		h = −10→10
Tmin = 0.975, Tmax = 0.989k = −19→22
23482 measured reflectionsl = −18→18
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)] = 0.065Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.169H atoms treated by a mixture of independent and constrained refinement
S = 1.03 w = 1/[σ2(Fo2) + (0.0744P)2 + 0.3238P]
where P = (Fo2 + 2Fc2)/3
4642 reflections(Δ/σ)max < 0.001
310 parametersΔρmax = 0.29 e Å−3
0 restraintsΔρmin = −0.18 e Å−3
Crystal data top
C38H44N10O24+·4(NO3−)V = 2125.5 (3) Å3
Mr = 920.87Z = 2
Monoclinic, P21/cMo Kα radiation
a = 8.4296 (6) ŵ = 0.11 mm−1
b = 17.6744 (12) ÅT = 294 K
c = 14.279 (1) Å0.20 × 0.12 × 0.10 mm
β = 92.421 (1)°
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer		4642 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2001)		2655 reflections with I > 2σ(I)
Tmin = 0.975, Tmax = 0.989Rint = 0.067
23482 measured reflectionsθmax = 27.0°
Refinement top
R[F2 > 2σ(F2)] = 0.065H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.169Δρmax = 0.29 e Å−3
S = 1.03Δρmin = −0.18 e Å−3
4642 reflectionsAbsolute structure: ?
310 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.2091 (3)0.53564 (19)0.38291 (19)0.0604 (8)
H1A0.22690.58950.37590.072*
H1B0.13980.52840.43470.072*
C20.1299 (3)0.50482 (16)0.29426 (18)0.0481 (7)
H2A0.12470.45020.30060.058*
H2B0.02140.52330.29110.058*
C30.2078 (3)0.60132 (15)0.1804 (2)0.0516 (7)
H3A0.27770.60790.12870.062*
H3B0.25320.62870.23390.062*
C40.0490 (3)0.63386 (16)0.15382 (17)0.0439 (6)
C5−0.2006 (3)0.64709 (15)0.10256 (16)0.0402 (6)
C6−0.3564 (3)0.63661 (16)0.06912 (18)0.0482 (7)
H6−0.39760.58870.05620.058*
C7−0.4458 (3)0.70087 (19)0.05621 (18)0.0538 (8)
H7−0.55050.69640.03370.065*
C8−0.3840 (3)0.77308 (17)0.07599 (19)0.0550 (8)
H8−0.44910.81520.06700.066*
C9−0.2306 (3)0.78310 (16)0.10818 (18)0.0510 (7)
H9−0.18920.83100.12050.061*
C10−0.1396 (3)0.71858 (15)0.12152 (17)0.0420 (6)
C110.3475 (3)0.48165 (16)0.1873 (2)0.0505 (7)
H11A0.42230.49070.23950.061*
H11B0.39320.50130.13100.061*
C120.3205 (3)0.39871 (16)0.17669 (17)0.0453 (7)
C130.2109 (3)0.28778 (17)0.14316 (17)0.0481 (7)
C140.1108 (4)0.22818 (18)0.11782 (19)0.0564 (8)
H140.00650.23610.09640.068*
C150.1746 (4)0.15673 (19)0.1262 (2)0.0666 (9)
H150.11200.11530.10880.080*
C160.3291 (5)0.1445 (2)0.1598 (2)0.0759 (10)
H160.36640.09510.16570.091*
C170.4284 (4)0.2034 (2)0.1844 (2)0.0676 (9)
H170.53240.19520.20630.081*
C180.3663 (3)0.27573 (17)0.17529 (18)0.0508 (7)
C190.4248 (3)0.52156 (19)0.49117 (19)0.0605 (8)
H19A0.35200.51130.54040.073*
H19B0.44680.57540.49070.073*
N10.1992 (2)0.52134 (12)0.20352 (14)0.0427 (5)
N2−0.0788 (2)0.59601 (14)0.12376 (15)0.0450 (6)
H2−0.084 (3)0.5449 (17)0.1178 (18)0.054*
N30.0169 (3)0.70765 (14)0.15369 (15)0.0465 (6)
H30.085 (3)0.7437 (16)0.1678 (18)0.056*
N40.4296 (3)0.34628 (16)0.19490 (16)0.0548 (7)
H40.516 (4)0.3587 (17)0.218 (2)0.066*
N50.1875 (3)0.36534 (14)0.14572 (15)0.0456 (6)
H50.106 (3)0.3912 (16)0.1281 (19)0.055*
N60.7793 (3)0.37255 (17)0.32131 (19)0.0621 (7)
O10.3557 (2)0.49900 (11)0.40309 (12)0.0566 (5)
O20.6974 (3)0.42656 (14)0.29412 (17)0.0876 (8)
O30.8884 (3)0.37929 (14)0.38036 (19)0.0902 (8)
O40.7453 (3)0.30882 (15)0.28733 (18)0.0908 (8)
N7−0.2022 (3)0.41060 (15)0.06511 (16)0.0546 (6)
O5−0.3230 (2)0.44713 (13)0.04530 (17)0.0787 (7)
O6−0.0836 (2)0.44321 (12)0.10178 (17)0.0766 (7)
O7−0.1903 (3)0.34285 (14)0.0487 (2)0.0942 (9)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0578 (18)0.075 (2)0.0474 (17)0.0142 (16)−0.0083 (13)−0.0031 (15)
C20.0402 (14)0.0546 (18)0.0488 (16)0.0041 (13)−0.0059 (12)0.0025 (13)
C30.0405 (14)0.0479 (18)0.0652 (18)−0.0094 (12)−0.0127 (13)0.0071 (14)
C40.0427 (14)0.0443 (18)0.0442 (15)−0.0071 (12)−0.0053 (11)0.0033 (12)
C50.0433 (14)0.0412 (16)0.0360 (13)0.0016 (12)0.0003 (11)0.0054 (11)
C60.0455 (14)0.0530 (18)0.0455 (15)−0.0055 (13)−0.0057 (12)0.0012 (13)
C70.0441 (15)0.070 (2)0.0469 (16)0.0052 (15)−0.0040 (12)0.0087 (14)
C80.0589 (18)0.055 (2)0.0504 (17)0.0157 (15)−0.0009 (14)0.0098 (14)
C90.0621 (18)0.0461 (18)0.0447 (16)0.0003 (14)0.0032 (13)−0.0003 (13)
C100.0459 (14)0.0434 (17)0.0364 (14)0.0002 (12)−0.0033 (11)0.0027 (11)
C110.0367 (14)0.062 (2)0.0527 (17)−0.0006 (13)−0.0044 (12)0.0033 (14)
C120.0409 (14)0.0554 (19)0.0395 (14)0.0031 (13)−0.0007 (11)0.0018 (13)
C130.0538 (16)0.055 (2)0.0356 (14)0.0063 (14)0.0035 (12)0.0021 (13)
C140.0645 (18)0.058 (2)0.0470 (16)−0.0045 (16)0.0040 (14)−0.0006 (14)
C150.092 (2)0.052 (2)0.0566 (19)−0.0009 (18)0.0123 (17)0.0033 (15)
C160.111 (3)0.059 (2)0.058 (2)0.021 (2)0.005 (2)0.0032 (17)
C170.075 (2)0.072 (2)0.0546 (19)0.0264 (19)−0.0056 (16)0.0036 (17)
C180.0571 (17)0.056 (2)0.0393 (15)0.0119 (15)0.0001 (12)−0.0011 (13)
C190.0645 (19)0.070 (2)0.0456 (17)0.0011 (15)−0.0152 (14)−0.0014 (14)
N10.0360 (11)0.0454 (14)0.0460 (13)−0.0016 (10)−0.0062 (9)0.0050 (10)
N20.0433 (12)0.0399 (13)0.0507 (13)−0.0031 (11)−0.0087 (10)0.0027 (11)
N30.0482 (13)0.0407 (15)0.0499 (13)−0.0080 (10)−0.0078 (10)−0.0014 (11)
N40.0441 (13)0.0697 (18)0.0498 (14)0.0114 (13)−0.0078 (11)0.0008 (12)
N50.0409 (12)0.0483 (16)0.0469 (13)0.0074 (11)−0.0052 (10)−0.0007 (11)
N60.0457 (14)0.066 (2)0.0738 (18)0.0063 (14)−0.0011 (13)0.0094 (15)
O10.0544 (11)0.0675 (14)0.0464 (11)0.0091 (10)−0.0150 (9)−0.0071 (9)
O20.0809 (16)0.0818 (18)0.0986 (18)0.0335 (14)−0.0129 (14)0.0038 (14)
O30.0605 (14)0.0913 (19)0.116 (2)−0.0012 (13)−0.0352 (14)0.0062 (15)
O40.0764 (16)0.0726 (18)0.121 (2)0.0040 (14)−0.0302 (15)−0.0099 (15)
N70.0473 (14)0.0551 (17)0.0602 (15)−0.0020 (12)−0.0134 (11)−0.0018 (12)
O50.0533 (12)0.0746 (16)0.1052 (18)0.0111 (11)−0.0310 (12)−0.0085 (13)
O60.0480 (12)0.0495 (13)0.129 (2)−0.0029 (10)−0.0305 (12)−0.0134 (12)
O70.0891 (17)0.0481 (15)0.141 (2)0.0016 (13)−0.0459 (16)−0.0181 (15)
Geometric parameters (Å, °) top
C1—O11.414 (3)C12—N41.323 (3)
C1—C21.508 (4)C12—N51.326 (3)
C1—H1A0.9700C13—N51.386 (4)
C1—H1B0.9700C13—C181.386 (4)
C2—N11.473 (3)C13—C141.388 (4)
C2—H2A0.9700C14—C151.376 (4)
C2—H2B0.9700C14—H140.9300
C3—N11.454 (3)C15—C161.385 (5)
C3—C41.491 (3)C15—H150.9300
C3—H3A0.9700C16—C171.374 (5)
C3—H3B0.9700C16—H160.9300
C4—N21.324 (3)C17—C181.385 (4)
C4—N31.332 (3)C17—H170.9300
C5—C101.387 (4)C18—N41.380 (4)
C5—C61.391 (3)C19—O11.421 (3)
C5—N21.391 (3)C19—C19i1.491 (6)
C6—C71.371 (4)C19—H19A0.9700
C6—H60.9300C19—H19B0.9700
C7—C81.403 (4)N2—H20.91 (3)
C7—H70.9300N3—H30.87 (3)
C8—C91.366 (4)N4—H40.82 (3)
C8—H80.9300N5—H50.86 (3)
C9—C101.383 (4)N6—O31.227 (3)
C9—H90.9300N6—O21.231 (3)
C10—N31.392 (3)N6—O41.255 (3)
C11—N11.460 (3)N7—O71.225 (3)
C11—C121.490 (4)N7—O51.228 (3)
C11—H11A0.9700N7—O61.249 (3)
C11—H11B0.9700
O1—C1—C2111.0 (2)C18—C13—C14121.7 (3)
O1—C1—H1A109.4C15—C14—C13116.3 (3)
C2—C1—H1A109.4C15—C14—H14121.9
O1—C1—H1B109.4C13—C14—H14121.9
C2—C1—H1B109.4C14—C15—C16122.1 (3)
H1A—C1—H1B108.0C14—C15—H15118.9
N1—C2—C1119.3 (2)C16—C15—H15118.9
N1—C2—H2A107.5C17—C16—C15121.6 (3)
C1—C2—H2A107.5C17—C16—H16119.2
N1—C2—H2B107.5C15—C16—H16119.2
C1—C2—H2B107.5C16—C17—C18116.9 (3)
H2A—C2—H2B107.0C16—C17—H17121.6
N1—C3—C4112.3 (2)C18—C17—H17121.6
N1—C3—H3A109.1N4—C18—C17132.3 (3)
C4—C3—H3A109.1N4—C18—C13106.3 (2)
N1—C3—H3B109.1C17—C18—C13121.4 (3)
C4—C3—H3B109.1O1—C19—C19i108.7 (3)
H3A—C3—H3B107.9O1—C19—H19A110.0
N2—C4—N3109.4 (2)C19i—C19—H19A110.0
N2—C4—C3126.6 (3)O1—C19—H19B110.0
N3—C4—C3124.0 (2)C19i—C19—H19B110.0
C10—C5—C6121.7 (2)H19A—C19—H19B108.3
C10—C5—N2106.5 (2)C3—N1—C11112.3 (2)
C6—C5—N2131.8 (2)C3—N1—C2114.7 (2)
C7—C6—C5116.2 (3)C11—N1—C2114.7 (2)
C7—C6—H6121.9C4—N2—C5109.0 (2)
C5—C6—H6121.9C4—N2—H2124.5 (17)
C6—C7—C8121.9 (3)C5—N2—H2126.5 (17)
C6—C7—H7119.0C4—N3—C10109.0 (2)
C8—C7—H7119.0C4—N3—H3125.6 (18)
C9—C8—C7121.6 (3)C10—N3—H3125.2 (18)
C9—C8—H8119.2C12—N4—C18109.5 (2)
C7—C8—H8119.2C12—N4—H4119 (2)
C8—C9—C10116.8 (3)C18—N4—H4131 (2)
C8—C9—H9121.6C12—N5—C13109.3 (2)
C10—C9—H9121.6C12—N5—H5121.4 (19)
C9—C10—C5121.7 (2)C13—N5—H5129.3 (19)
C9—C10—N3132.2 (3)O3—N6—O2122.4 (3)
C5—C10—N3106.1 (2)O3—N6—O4120.3 (3)
N1—C11—C12111.2 (2)O2—N6—O4117.3 (3)
N1—C11—H11A109.4C1—O1—C19112.0 (2)
C12—C11—H11A109.4N6—O2—H495.9 (8)
N1—C11—H11B109.4N6—O4—H489.8 (8)
C12—C11—H11B109.4O7—N7—O5122.9 (2)
H11A—C11—H11B108.0O7—N7—O6117.4 (2)
N4—C12—N5108.9 (3)O5—N7—O6119.6 (3)
N4—C12—C11124.6 (2)N7—O6—H2120.4 (9)
N5—C12—C11126.5 (2)N7—O6—H5121.3 (8)
N5—C13—C18106.1 (2)H2—O6—H5117.9 (12)
N5—C13—C14132.2 (3)
O1—C1—C2—N1−69.8 (3)C12—C11—N1—C267.7 (3)
N1—C3—C4—N2−21.2 (4)C1—C2—N1—C3−60.6 (3)
N1—C3—C4—N3161.5 (2)C1—C2—N1—C1171.7 (3)
C10—C5—C6—C7−0.1 (4)N3—C4—N2—C50.2 (3)
N2—C5—C6—C7179.7 (3)C3—C4—N2—C5−177.4 (3)
C5—C6—C7—C8−0.3 (4)C10—C5—N2—C40.0 (3)
C6—C7—C8—C90.8 (4)C6—C5—N2—C4−179.9 (3)
C7—C8—C9—C10−0.8 (4)N2—C4—N3—C10−0.3 (3)
C8—C9—C10—C50.4 (4)C3—C4—N3—C10177.4 (2)
C8—C9—C10—N3−179.2 (3)C9—C10—N3—C4179.9 (3)
C6—C5—C10—C90.0 (4)C5—C10—N3—C40.3 (3)
N2—C5—C10—C9−179.9 (2)N5—C12—N4—C180.0 (3)
C6—C5—C10—N3179.7 (2)C11—C12—N4—C18−178.4 (2)
N2—C5—C10—N3−0.1 (3)C17—C18—N4—C12−178.0 (3)
N1—C11—C12—N4−154.4 (2)C13—C18—N4—C120.3 (3)
N1—C11—C12—N527.5 (4)N4—C12—N5—C13−0.3 (3)
N5—C13—C14—C15−178.5 (3)C11—C12—N5—C13178.1 (2)
C18—C13—C14—C15−0.1 (4)C18—C13—N5—C120.5 (3)
C13—C14—C15—C161.2 (4)C14—C13—N5—C12179.0 (3)
C14—C15—C16—C17−1.6 (5)C2—C1—O1—C19−174.0 (2)
C15—C16—C17—C180.8 (5)C19i—C19—O1—C1177.9 (3)
C16—C17—C18—N4178.5 (3)O3—N6—O2—H4−169.1 (8)
C16—C17—C18—C130.3 (4)O4—N6—O2—H49.7 (8)
N5—C13—C18—N4−0.5 (3)O3—N6—O4—H4169.7 (8)
C14—C13—C18—N4−179.2 (2)O2—N6—O4—H4−9.1 (8)
N5—C13—C18—C17178.1 (2)O7—N7—O6—H2173.8 (10)
C14—C13—C18—C17−0.7 (4)O5—N7—O6—H2−4.6 (10)
C4—C3—N1—C11153.5 (2)O7—N7—O6—H51.3 (10)
C4—C3—N1—C2−73.1 (3)O5—N7—O6—H5−177.1 (10)
C12—C11—N1—C3−158.9 (2)
Symmetry codes: (i) −x+1, −y+1, −z+1.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C14—H14···O70.932.583.364 (4)142
C11—H11A···O10.972.433.094 (3)125
C6—H6···O50.932.593.379 (4)143
N4—H4···O40.82 (3)2.31 (3)2.995 (3)142 (3)
N4—H4···O20.82 (3)2.20 (3)2.975 (4)160 (3)
N5—H5···O60.86 (3)1.87 (3)2.719 (3)174 (3)
N2—H2···O60.91 (3)1.81 (3)2.719 (3)177 (3)
C7—H7···O7ii0.932.533.443 (4)166
N3—H3···O4iii0.87 (3)1.93 (3)2.789 (3)169 (3)
N3—H3···O3iii0.87 (3)2.51 (3)3.180 (3)134 (2)
Symmetry codes: (ii) −x−1, −y+1, −z; (iii) −x+1, y+1/2, −z+1/2.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C14—H14···O70.932.583.364 (4)142
C11—H11A···O10.972.433.094 (3)125
C6—H6···O50.932.593.379 (4)143
N4—H4···O40.82 (3)2.31 (3)2.995 (3)142 (3)
N4—H4···O20.82 (3)2.20 (3)2.975 (4)160 (3)
N5—H5···O60.86 (3)1.87 (3)2.719 (3)174 (3)
N2—H2···O60.91 (3)1.81 (3)2.719 (3)177 (3)
C7—H7···O7i0.932.533.443 (4)166
N3—H3···O4ii0.87 (3)1.93 (3)2.789 (3)169 (3)
N3—H3···O3ii0.87 (3)2.51 (3)3.180 (3)134 (2)
Symmetry codes: (i) −x−1, −y+1, −z; (ii) −x+1, y+1/2, −z+1/2.
Acknowledgements top

This work was financially supported mostly by Key Fundamental Project No. 2002CCA00500.

references
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