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

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ISSN: 2056-9890

Tris(1H-benzimidazol-3-ium-2-ylmeth­yl)amine tris­­(2,4,6-tri­nitro­phenolate) aceto­nitrile disolvate

aSchool of Chemical and Biological Engineering, Lanzhou Jiaotong University, Lanzhou 730070, People's Republic of China
*Correspondence e-mail: wuhuilu@163.com

(Received 11 May 2012; accepted 21 May 2012; online 31 May 2012)

In the cation of the title salt, C24H24N73+·3C6H2N3O7·2C2H3N, the three benzimidazolium ring systems are oriented to each other at dihedral angles of 10.42 (7), 23.98 (7) and 22.17 (7)°. In the crystal, the cation links to the adjacent picrate anions via N—H⋯O hydrogen bonds; one of independent acetonitrile solvent mol­ecules is also linked to the cation via an N—H⋯N hydrogen bond.

Related literature

For background to benzimidazoles and their derivatives, see: Wilkinson (1987[Wilkinson, G. (1987). In Comprehensive Coordination Chemistry. Oxford University Press.]); Siya et al. (1992[Siya, R., Dean, S. W., Linda, L. W., John, W. M. & Leroy, B. T. (1992). J. Med. Chem. 35, 539-547.]); Horton et al. (2003[Horton, D. A., Bourne, G. T. & Smythe, M. L. (2003). Chem. Rev. 103, 893-930.]); Prados & Quesada (2008[Prados, P. & Quesada, R. (2008). Supramol. Chem. 20, 201-216.]); Steed (2009[Steed, J. W. (2009). Chem. Soc. Rev. 38, 506-519.]); Aghabozorg et al. (2008[Aghabozorg, H., Manteghi, F. & Sheshmani, S. (2008). J. Iran. Chem. Soc. 5, 184-227.]). For inter­molecular inter­actions, see: Blake et al. (2000[Blake, A. J., Hubberstey, P., Suksangpanya, U. & Wilson, C. L. (2000). J. Chem. Soc. Dalton Trans. pp. 3873-3880.]); Bourne et al. (2001[Bourne, S. A., Lu, J., Moulton, B. & Zaworotko, M. J. (2001). Chem. Commun. 10, 861-862.]); Desiraju (2000[Desiraju, G. R. (2000). J. Chem. Soc. Dalton Trans. pp. 3745-3751.]). For our previous model studies, see: Liu et al. (2011[Liu, B., Kou, F., Jia, F., Yuan, J. & Wu, H. (2011). Acta Cryst. E67, o1816.]);

[Scheme 1]

Experimental

Crystal data
  • C24H24N73+·3C6H2N3O7·2C2H3N

  • Mr = 1176.93

  • Triclinic, [P \overline 1]

  • a = 10.9914 (3) Å

  • b = 15.4620 (5) Å

  • c = 16.1760 (6) Å

  • α = 74.826 (1)°

  • β = 74.337 (1)°

  • γ = 73.299 (1)°

  • V = 2484.29 (14) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.13 mm−1

  • T = 153 K

  • 0.38 × 0.36 × 0.30 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • 18903 measured reflections

  • 8608 independent reflections

  • 6896 reflections with I > 2σ(I)

  • Rint = 0.016

Refinement
  • R[F2 > 2σ(F2)] = 0.037

  • wR(F2) = 0.127

  • S = 1.14

  • 8608 reflections

  • 769 parameters

  • H-atom parameters constrained

  • Δρmax = 0.60 e Å−3

  • Δρmin = −0.52 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N1—H1A⋯O1 0.88 1.96 2.834 (2) 173
N2—H2A⋯O15i 0.88 1.88 2.619 (2) 140
N2—H2A⋯O16i 0.88 2.27 2.952 (2) 134
N3—H3A⋯O1 0.88 2.01 2.847 (2) 158
N3—H3A⋯O7 0.88 2.33 2.905 (2) 123
N4—H4A⋯N17ii 0.88 2.18 2.965 (3) 148
N5—H5A⋯O1 0.88 2.28 2.836 (2) 121
N5—H5A⋯O2 0.88 2.09 2.853 (2) 144
N6—H6A⋯O8iii 0.88 1.91 2.693 (2) 147
N6—H6A⋯O14iii 0.88 2.30 2.945 (2) 130
Symmetry codes: (i) -x+1, -y+2, -z+1; (ii) -x+1, -y+2, -z; (iii) x, y+1, z.

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

It is well known that benzimidazole is a typical heterocyclic ligand with nitrogen donor and a component of biologically important molecules (Wilkinson et al., 1987). Those compounds are environmentally friendly compounds with two high active nitrogen atoms in 1, 3-sites (Siya et al. 1992). Benzimidazoles and their derivatives being ubiquitous, quite a few of them play important roles in biological, aquatic, environmental, and industrial processes, fungicide and many other fields (Horton et al., 2003; Steed, 2009; Prados & Quesada, 2008). According to the previous report (Aghabozorg et al., 2008), H. Aghabozorg et al. focused on the proton delivery from acids, which are considered as suitable proton donors, to amines as proton acceptors. The results were production of several proton transfer ion pairs possessing some remaining donor sites applied for coordination to metallic centers in preparation of metal-organic structures. Much of the investigations show that the proton compound exist various interactions including hydrogen bondings, ion pairing, van der Waals and so on (Bourne et al., 2001; Desiraju et al., 2000; Blake et al., 2000).

In our previous model studies (Liu et al., 2011) that the bis(N-methylbenzimidazol-2-ylmethyl) aniline (MEBBA) cation attacked by a picrate anion bridge with proton transfer and formation of a novel complex, now we used similar method to synthesize the title compound. The title compound is a proton transfer compound that consists of a tris (2-benzimidazolylmethyl) amine cation, three picrate anions and diacetonitrile solvents. Three protons from three picrate anion transfer to N (double bond) fromtris (2-benzimidazolylmethyl) amine cation. The proton transfer compound is formed by picrate anions and amines can enhance the intermolecular forces between the obtained cationic and anionic fragments, and interactions described above can provide a large part of the stabilization energy of resulting self-assembly systems (Aghabozorg et al., 2008). The crystal structure is mainly stabilized by N—H—N intramolecular hydrogen bond. In this paper, the crystal unit of the title proton transfer compound be composed and the proton of the picric acid is transferred to the nitrogen atoms of the ntb (Fig. 1), and formed by tripod structrue. The angle of C9–N7–C17 is 108.15°, C8–N17–C7 is 112.55°, C8–N7–C9 is 110.46° respectively. From the crystal structure we can see that there is one ntb ligand containing three N—H bonds as hydrogen-bonding donors, each forming an N—H—O hydrogen bond with the surrounding picrate anions.

Related literature top

For background to benzimidazoles and their derivatives, see: Wilkinson (1987); Siya et al. (1992); Horton et al. (2003); Prados & Quesada (2008); Steed (2009); Aghabozorg et al. (2008). For intermolecular interactions, see: Blake et al. (2000); Bourne et al. (2001); Desiraju (2000). For our previous model studies, see: Liu et al. (2011);

Experimental top

Reagents and solvents used were of commercially available quality. To a stirred solution of tris (2-benzimidazolylmethyl)amine (0.4070 g, 1 mmol) in hot acetonitrile (10 ml) was added picrate acid (0.2291 g, 1 mmol) solution dissolved in acetonitrile (5 ml) over 4-5 h at room temperature, then the clear filtrate was collected from the resulting solution. The crystallized corresponding products were obtained from the filtrates by allowing slow evaporation of the solvent at room temperaturethe. (Yield 0.401 g, 63%). Elemental analysis found: C, 47.02%; H, 3.02%; N, 21.37%; calcd. for C46H36N81O21: C, 46.95%; H, 3.08%; N,21.42%.

Refinement top

H atoms were found in difference electron maps and were subsequently refined in a riding-model approximation with C—H = 0.95 to 0.99 Å and N—H = 0.88 Å, Uiso(H) = 1.2Ueq(C,N).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The title compound with displacement ellipsoides drawn at the 30% probability level. H atoms bonded to C atoms have been omitted for clarity.
Tris(1H-benzimidazol-3-ium-2-ylmethyl)amine tris(2,4,6-trinitrophenolate) acetonitrile disolvate top
Crystal data top
C24H24N73+·3C6H2N3O7·2C2H3NZ = 2
Mr = 1176.93F(000) = 1212
Triclinic, P1Dx = 1.573 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 10.9914 (3) ÅCell parameters from 8608 reflections
b = 15.4620 (5) Åθ = 3.0–25.0°
c = 16.1760 (6) ŵ = 0.13 mm1
α = 74.826 (1)°T = 153 K
β = 74.337 (1)°Block, yellow
γ = 73.299 (1)°0.38 × 0.36 × 0.30 mm
V = 2484.29 (14) Å3
Data collection top
Bruker APEXII CCD
diffractometer
6896 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.016
Graphite monochromatorθmax = 25.0°, θmin = 3.0°
ω scansh = 1313
18903 measured reflectionsk = 1818
8608 independent reflectionsl = 1919
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.037H-atom parameters constrained
wR(F2) = 0.127 w = 1/[σ2(Fo2) + (0.070P)2 + 0.7354P]
where P = (Fo2 + 2Fc2)/3
S = 1.14(Δ/σ)max = 0.003
8608 reflectionsΔρmax = 0.60 e Å3
769 parametersΔρmin = 0.52 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0048 (7)
Crystal data top
C24H24N73+·3C6H2N3O7·2C2H3Nγ = 73.299 (1)°
Mr = 1176.93V = 2484.29 (14) Å3
Triclinic, P1Z = 2
a = 10.9914 (3) ÅMo Kα radiation
b = 15.4620 (5) ŵ = 0.13 mm1
c = 16.1760 (6) ÅT = 153 K
α = 74.826 (1)°0.38 × 0.36 × 0.30 mm
β = 74.337 (1)°
Data collection top
Bruker APEXII CCD
diffractometer
6896 reflections with I > 2σ(I)
18903 measured reflectionsRint = 0.016
8608 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0370 restraints
wR(F2) = 0.127H-atom parameters constrained
S = 1.14Δρmax = 0.60 e Å3
8608 reflectionsΔρmin = 0.52 e Å3
769 parameters
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
O10.19492 (13)0.72945 (9)0.17343 (9)0.0277 (3)
O20.39722 (16)0.60052 (13)0.11588 (14)0.0557 (5)
O30.36658 (17)0.47442 (13)0.10886 (18)0.0768 (7)
O40.03082 (14)0.38847 (10)0.21627 (11)0.0376 (4)
O50.20832 (15)0.49423 (12)0.23218 (13)0.0488 (5)
O60.18403 (14)0.78337 (11)0.28475 (10)0.0373 (4)
O70.04156 (14)0.84451 (10)0.18413 (11)0.0387 (4)
O80.55319 (13)0.01411 (9)0.21443 (9)0.0287 (3)
O90.45012 (15)0.11421 (11)0.08342 (10)0.0382 (4)
O100.54969 (15)0.22461 (11)0.04584 (10)0.0368 (4)
O110.4936 (2)0.37383 (13)0.28626 (13)0.0709 (6)
O120.5011 (2)0.29227 (13)0.41583 (12)0.0557 (5)
O130.61627 (14)0.04480 (11)0.44910 (10)0.0412 (4)
O140.49248 (17)0.08665 (11)0.39075 (10)0.0435 (4)
O150.80096 (18)0.92619 (10)0.63659 (10)0.0455 (4)
O160.86187 (18)0.99626 (11)0.46725 (10)0.0468 (4)
O170.91497 (14)0.90721 (11)0.37525 (9)0.0365 (4)
O180.8705 (2)0.59992 (13)0.45699 (13)0.0583 (5)
O190.8206 (2)0.53622 (13)0.59356 (15)0.0723 (6)
O200.74359 (14)0.70416 (10)0.81857 (10)0.0343 (4)
O210.84323 (16)0.81413 (11)0.78892 (10)0.0402 (4)
N10.19365 (15)0.80823 (11)0.31345 (11)0.0235 (4)
H1A0.19040.78870.26780.028*
N20.20614 (15)0.89781 (11)0.39250 (10)0.0238 (4)
H2A0.21290.94670.40750.029*
N30.16194 (15)0.88274 (11)0.03191 (11)0.0244 (4)
H3A0.15540.84510.08330.029*
N40.19477 (15)1.00153 (11)0.06998 (10)0.0236 (4)
H4A0.21321.05510.09660.028*
N50.44272 (15)0.73101 (11)0.19350 (11)0.0252 (4)
H5A0.41200.71400.15690.030*
N60.50621 (15)0.81663 (11)0.25280 (10)0.0227 (4)
H6A0.52380.86500.26180.027*
N70.25878 (15)0.93287 (11)0.15208 (10)0.0218 (3)
N80.32617 (16)0.54937 (12)0.12943 (12)0.0307 (4)
N90.08945 (16)0.46810 (12)0.22038 (12)0.0310 (4)
N100.08201 (16)0.77711 (12)0.22959 (11)0.0285 (4)
N110.50651 (16)0.16298 (12)0.10090 (11)0.0270 (4)
N120.5052 (2)0.29939 (14)0.33842 (13)0.0414 (5)
N130.55052 (16)0.03116 (12)0.39430 (11)0.0297 (4)
N140.87694 (16)0.92056 (12)0.45101 (11)0.0280 (4)
N150.8432 (2)0.60241 (14)0.53516 (15)0.0453 (5)
N160.79938 (16)0.76219 (11)0.76568 (11)0.0279 (4)
N180.9138 (2)0.42750 (16)0.01524 (15)0.0541 (6)
N170.76021 (19)0.81449 (14)0.08431 (13)0.0401 (5)
C10.18632 (18)0.75699 (13)0.39846 (13)0.0256 (4)
C20.1757 (2)0.66653 (15)0.43415 (15)0.0335 (5)
H2B0.17050.62720.39950.040*
C30.1730 (2)0.63736 (16)0.52277 (16)0.0392 (6)
H3B0.16610.57600.54980.047*
C40.1801 (2)0.69480 (16)0.57392 (15)0.0401 (6)
H4B0.17800.67160.63470.048*
C50.1901 (2)0.78520 (15)0.53837 (14)0.0330 (5)
H5B0.19450.82470.57310.040*
C60.19351 (18)0.81461 (13)0.44906 (13)0.0247 (4)
C70.20641 (17)0.89165 (13)0.31229 (12)0.0212 (4)
C80.22002 (19)0.96737 (13)0.23388 (12)0.0252 (4)
H8A0.13621.01360.23460.030*
H8B0.28590.99830.23650.030*
C90.2139 (2)1.00563 (13)0.08031 (13)0.0259 (4)
H9A0.27941.04290.05270.031*
H9B0.13161.04690.10380.031*
C100.19338 (17)0.96346 (13)0.01371 (12)0.0221 (4)
C110.16236 (17)0.94336 (13)0.10929 (12)0.0226 (4)
C120.15096 (18)0.95044 (15)0.19487 (13)0.0285 (5)
H12A0.16471.00240.23980.034*
C130.1184 (2)0.87699 (15)0.20989 (14)0.0330 (5)
H13A0.11100.87800.26730.040*
C140.0957 (2)0.80077 (16)0.14332 (15)0.0356 (5)
H14A0.07250.75220.15680.043*
C150.1064 (2)0.79473 (15)0.05901 (15)0.0329 (5)
H15A0.09080.74330.01380.040*
C160.14117 (18)0.86745 (14)0.04346 (13)0.0251 (4)
C170.40172 (18)0.89956 (14)0.12558 (13)0.0248 (4)
H17A0.44440.94900.12230.030*
H17B0.42350.88470.06660.030*
C180.45217 (17)0.81625 (13)0.18870 (12)0.0225 (4)
C190.53047 (18)0.72800 (13)0.30347 (13)0.0239 (4)
C200.58034 (19)0.69227 (14)0.37957 (13)0.0295 (5)
H20A0.60850.72920.40580.035*
C210.5861 (2)0.60002 (15)0.41413 (14)0.0343 (5)
H21A0.61900.57270.46600.041*
C220.5453 (2)0.54537 (15)0.37567 (15)0.0360 (5)
H22A0.55200.48200.40190.043*
C230.4956 (2)0.58018 (14)0.30116 (15)0.0319 (5)
H23A0.46720.54290.27530.038*
C240.48936 (18)0.67315 (13)0.26583 (13)0.0251 (4)
C250.13096 (18)0.66971 (13)0.18346 (12)0.0233 (4)
C260.18751 (18)0.57814 (13)0.16620 (13)0.0238 (4)
C270.11648 (19)0.51360 (13)0.17898 (13)0.0254 (4)
H27A0.15850.45440.16590.030*
C280.01533 (18)0.53544 (13)0.21077 (13)0.0257 (4)
C290.07911 (19)0.62129 (14)0.22969 (13)0.0268 (4)
H29A0.17010.63540.25260.032*
C300.00806 (19)0.68566 (13)0.21469 (12)0.0247 (4)
C310.53576 (17)0.05662 (14)0.24384 (13)0.0233 (4)
C320.51996 (18)0.14913 (13)0.19069 (13)0.0235 (4)
C330.51562 (18)0.22584 (14)0.21939 (13)0.0273 (4)
H33A0.50910.28410.18060.033*
C340.52086 (19)0.21746 (14)0.30585 (14)0.0292 (5)
C350.53357 (19)0.13207 (14)0.36288 (13)0.0275 (4)
H35A0.53860.12660.42180.033*
C360.53860 (18)0.05687 (14)0.33255 (13)0.0247 (4)
C370.82270 (18)0.85297 (13)0.61195 (13)0.0249 (4)
C380.85192 (18)0.84327 (14)0.52128 (13)0.0247 (4)
C390.85685 (19)0.76357 (14)0.49720 (14)0.0294 (5)
H39A0.87380.76120.43690.035*
C400.8371 (2)0.68644 (14)0.56079 (15)0.0316 (5)
C410.81635 (19)0.68765 (14)0.64873 (14)0.0302 (5)
H41A0.80370.63420.69190.036*
C420.81428 (18)0.76644 (13)0.67287 (13)0.0248 (4)
C430.7582 (2)0.75207 (16)0.06067 (14)0.0324 (5)
C440.7551 (3)0.67206 (18)0.03153 (18)0.0490 (6)
H44A0.70950.63220.08010.059*
H44B0.84420.63800.01190.059*
H44C0.70970.69180.01710.059*
C450.8089 (3)0.43038 (17)0.05165 (17)0.0432 (6)
C460.6769 (3)0.4302 (2)0.0968 (2)0.0670 (9)
H46A0.64850.38350.08060.080*
H46B0.62080.49100.08030.080*
H46C0.67170.41590.16020.080*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0332 (7)0.0233 (7)0.0316 (8)0.0105 (6)0.0115 (6)0.0050 (6)
O20.0371 (9)0.0497 (11)0.0906 (15)0.0239 (8)0.0139 (9)0.0444 (10)
O30.0349 (10)0.0360 (11)0.157 (2)0.0079 (8)0.0050 (11)0.0422 (13)
O40.0393 (8)0.0234 (8)0.0521 (10)0.0098 (7)0.0112 (7)0.0066 (7)
O50.0279 (9)0.0421 (10)0.0789 (13)0.0131 (7)0.0019 (8)0.0206 (9)
O60.0355 (8)0.0348 (9)0.0396 (9)0.0084 (7)0.0026 (7)0.0145 (7)
O70.0425 (9)0.0213 (8)0.0445 (9)0.0076 (7)0.0006 (7)0.0020 (7)
O80.0380 (8)0.0228 (7)0.0291 (8)0.0099 (6)0.0071 (6)0.0082 (6)
O90.0554 (10)0.0374 (9)0.0324 (9)0.0202 (8)0.0164 (7)0.0070 (7)
O100.0469 (9)0.0341 (9)0.0279 (8)0.0176 (7)0.0045 (7)0.0019 (7)
O110.138 (2)0.0314 (10)0.0469 (12)0.0357 (11)0.0051 (12)0.0114 (9)
O120.0904 (14)0.0512 (12)0.0391 (11)0.0256 (10)0.0138 (9)0.0215 (9)
O130.0340 (8)0.0496 (10)0.0343 (9)0.0025 (7)0.0144 (7)0.0006 (7)
O140.0700 (11)0.0304 (9)0.0352 (9)0.0247 (8)0.0114 (8)0.0003 (7)
O150.0869 (13)0.0222 (8)0.0262 (8)0.0159 (8)0.0044 (8)0.0072 (7)
O160.0852 (13)0.0315 (9)0.0305 (9)0.0275 (9)0.0103 (8)0.0040 (7)
O170.0408 (8)0.0415 (9)0.0240 (8)0.0056 (7)0.0044 (6)0.0079 (7)
O180.0856 (14)0.0467 (11)0.0577 (13)0.0104 (10)0.0280 (10)0.0283 (9)
O190.1228 (19)0.0317 (11)0.0722 (15)0.0292 (11)0.0209 (13)0.0143 (10)
O200.0365 (8)0.0282 (8)0.0318 (8)0.0068 (6)0.0036 (6)0.0002 (7)
O210.0603 (10)0.0335 (9)0.0351 (9)0.0157 (8)0.0197 (8)0.0058 (7)
N10.0267 (8)0.0220 (9)0.0225 (9)0.0063 (7)0.0028 (6)0.0076 (7)
N20.0294 (9)0.0213 (9)0.0229 (9)0.0079 (7)0.0051 (7)0.0067 (7)
N30.0319 (9)0.0208 (9)0.0227 (9)0.0085 (7)0.0085 (7)0.0026 (7)
N40.0274 (8)0.0209 (8)0.0227 (9)0.0065 (7)0.0066 (6)0.0023 (7)
N50.0271 (8)0.0221 (9)0.0301 (9)0.0044 (7)0.0073 (7)0.0118 (7)
N60.0265 (8)0.0199 (8)0.0244 (9)0.0080 (7)0.0055 (6)0.0059 (7)
N70.0276 (8)0.0192 (8)0.0200 (8)0.0049 (6)0.0066 (6)0.0052 (6)
N80.0304 (9)0.0232 (10)0.0411 (11)0.0080 (8)0.0077 (8)0.0085 (8)
N90.0320 (10)0.0279 (10)0.0337 (10)0.0125 (8)0.0048 (7)0.0033 (8)
N100.0320 (9)0.0261 (10)0.0287 (9)0.0060 (7)0.0071 (7)0.0079 (8)
N110.0295 (9)0.0248 (9)0.0261 (9)0.0058 (7)0.0048 (7)0.0054 (7)
N120.0591 (13)0.0343 (11)0.0383 (12)0.0207 (9)0.0038 (9)0.0158 (9)
N130.0311 (9)0.0298 (10)0.0247 (9)0.0045 (8)0.0039 (7)0.0048 (7)
N140.0297 (9)0.0318 (10)0.0248 (9)0.0079 (7)0.0085 (7)0.0059 (8)
N150.0623 (13)0.0280 (11)0.0541 (14)0.0095 (9)0.0227 (11)0.0131 (10)
N160.0312 (9)0.0205 (9)0.0295 (10)0.0035 (7)0.0074 (7)0.0026 (8)
N180.0538 (14)0.0551 (15)0.0544 (14)0.0180 (11)0.0075 (11)0.0109 (11)
N170.0497 (12)0.0337 (11)0.0376 (11)0.0103 (9)0.0118 (9)0.0047 (9)
C10.0240 (10)0.0212 (10)0.0296 (11)0.0045 (8)0.0023 (8)0.0061 (8)
C20.0342 (11)0.0222 (11)0.0408 (13)0.0068 (9)0.0025 (9)0.0058 (9)
C30.0418 (13)0.0234 (11)0.0420 (14)0.0072 (9)0.0030 (10)0.0044 (10)
C40.0479 (14)0.0352 (13)0.0291 (12)0.0087 (10)0.0078 (10)0.0061 (10)
C50.0419 (12)0.0288 (12)0.0256 (11)0.0081 (9)0.0070 (9)0.0011 (9)
C60.0259 (10)0.0205 (10)0.0254 (10)0.0066 (8)0.0037 (8)0.0012 (8)
C70.0213 (9)0.0188 (10)0.0230 (10)0.0045 (7)0.0026 (7)0.0059 (8)
C80.0332 (11)0.0206 (10)0.0222 (10)0.0053 (8)0.0050 (8)0.0069 (8)
C90.0345 (11)0.0199 (10)0.0241 (10)0.0055 (8)0.0097 (8)0.0028 (8)
C100.0226 (9)0.0208 (10)0.0224 (10)0.0036 (7)0.0064 (7)0.0034 (8)
C110.0226 (9)0.0207 (10)0.0238 (10)0.0029 (8)0.0066 (7)0.0043 (8)
C120.0278 (10)0.0306 (11)0.0246 (11)0.0006 (8)0.0080 (8)0.0069 (9)
C130.0330 (11)0.0372 (13)0.0324 (12)0.0007 (9)0.0142 (9)0.0155 (10)
C140.0406 (12)0.0317 (12)0.0427 (13)0.0061 (10)0.0178 (10)0.0147 (10)
C150.0379 (12)0.0276 (11)0.0374 (12)0.0086 (9)0.0131 (9)0.0069 (9)
C160.0260 (10)0.0253 (10)0.0260 (11)0.0043 (8)0.0093 (8)0.0063 (8)
C170.0283 (10)0.0252 (10)0.0220 (10)0.0079 (8)0.0042 (8)0.0059 (8)
C180.0215 (9)0.0224 (10)0.0239 (10)0.0050 (8)0.0021 (7)0.0080 (8)
C190.0234 (9)0.0186 (10)0.0267 (10)0.0042 (8)0.0016 (8)0.0041 (8)
C200.0308 (11)0.0282 (11)0.0286 (11)0.0069 (9)0.0059 (8)0.0048 (9)
C210.0350 (11)0.0321 (12)0.0296 (12)0.0042 (9)0.0060 (9)0.0004 (9)
C220.0381 (12)0.0221 (11)0.0397 (13)0.0035 (9)0.0027 (10)0.0023 (9)
C230.0327 (11)0.0206 (11)0.0418 (13)0.0053 (8)0.0036 (9)0.0104 (9)
C240.0219 (9)0.0212 (10)0.0312 (11)0.0026 (8)0.0026 (8)0.0093 (8)
C250.0310 (10)0.0225 (10)0.0186 (10)0.0091 (8)0.0098 (8)0.0003 (8)
C260.0269 (10)0.0209 (10)0.0244 (10)0.0066 (8)0.0078 (8)0.0023 (8)
C270.0334 (11)0.0177 (10)0.0260 (11)0.0065 (8)0.0100 (8)0.0013 (8)
C280.0305 (10)0.0215 (10)0.0270 (11)0.0115 (8)0.0070 (8)0.0010 (8)
C290.0291 (10)0.0268 (11)0.0243 (10)0.0085 (8)0.0056 (8)0.0026 (8)
C300.0327 (10)0.0191 (10)0.0216 (10)0.0055 (8)0.0064 (8)0.0027 (8)
C310.0219 (9)0.0244 (11)0.0252 (10)0.0080 (8)0.0044 (7)0.0052 (8)
C320.0250 (10)0.0228 (10)0.0243 (10)0.0071 (8)0.0053 (7)0.0056 (8)
C330.0279 (10)0.0240 (11)0.0304 (11)0.0089 (8)0.0044 (8)0.0048 (9)
C340.0338 (11)0.0274 (11)0.0315 (11)0.0123 (9)0.0045 (8)0.0113 (9)
C350.0292 (10)0.0331 (12)0.0249 (10)0.0121 (9)0.0069 (8)0.0071 (9)
C360.0240 (10)0.0246 (10)0.0259 (11)0.0076 (8)0.0054 (8)0.0036 (8)
C370.0274 (10)0.0205 (10)0.0277 (11)0.0065 (8)0.0051 (8)0.0062 (8)
C380.0241 (10)0.0242 (10)0.0279 (11)0.0045 (8)0.0090 (8)0.0063 (8)
C390.0309 (11)0.0312 (12)0.0301 (11)0.0037 (9)0.0121 (8)0.0109 (9)
C400.0368 (11)0.0223 (11)0.0412 (13)0.0057 (9)0.0151 (9)0.0101 (9)
C410.0318 (11)0.0232 (11)0.0366 (12)0.0056 (8)0.0120 (9)0.0035 (9)
C420.0256 (10)0.0208 (10)0.0284 (11)0.0031 (8)0.0080 (8)0.0060 (8)
C430.0367 (12)0.0293 (12)0.0292 (12)0.0066 (9)0.0083 (9)0.0022 (10)
C440.0597 (16)0.0386 (14)0.0520 (16)0.0052 (12)0.0166 (12)0.0166 (12)
C450.0488 (15)0.0367 (14)0.0475 (15)0.0114 (11)0.0126 (12)0.0099 (11)
C460.0474 (16)0.071 (2)0.086 (2)0.0178 (15)0.0045 (15)0.0270 (18)
Geometric parameters (Å, º) top
O1—C251.268 (2)C5—H5B0.9500
O2—N81.206 (2)C7—C81.491 (3)
O3—N81.215 (2)C8—H8A0.9900
O4—N91.224 (2)C8—H8B0.9900
O5—N91.228 (2)C9—C101.490 (3)
O6—N101.227 (2)C9—H9A0.9900
O7—N101.230 (2)C9—H9B0.9900
O8—C311.250 (2)C11—C161.391 (3)
O9—N111.228 (2)C11—C121.397 (3)
O10—N111.230 (2)C12—C131.379 (3)
O11—N121.232 (3)C12—H12A0.9500
O12—N121.218 (3)C13—C141.404 (3)
O13—N131.230 (2)C13—H13A0.9500
O14—N131.227 (2)C14—C151.377 (3)
O15—C371.236 (2)C14—H14A0.9500
O16—N141.222 (2)C15—C161.386 (3)
O17—N141.235 (2)C15—H15A0.9500
O18—N151.227 (3)C17—C181.489 (3)
O19—N151.231 (3)C17—H17A0.9900
O20—N161.243 (2)C17—H17B0.9900
O21—N161.224 (2)C19—C241.390 (3)
N1—C71.332 (2)C19—C201.398 (3)
N1—C11.390 (3)C20—C211.379 (3)
N1—H1A0.8800C20—H20A0.9500
N2—C71.325 (2)C21—C221.395 (3)
N2—C61.389 (3)C21—H21A0.9500
N2—H2A0.8800C22—C231.373 (3)
N3—C101.328 (3)C22—H22A0.9500
N3—C161.388 (3)C23—C241.390 (3)
N3—H3A0.8800C23—H23A0.9500
N4—C101.325 (2)C25—C261.441 (3)
N4—C111.395 (3)C25—C301.443 (3)
N4—H4A0.8800C26—C271.379 (3)
N5—C181.332 (3)C27—C281.373 (3)
N5—C241.394 (3)C27—H27A0.9500
N5—H5A0.8800C28—C291.382 (3)
N6—C181.329 (2)C29—C301.370 (3)
N6—C191.393 (2)C29—H29A0.9500
N6—H6A0.8800C31—C361.445 (3)
N7—C81.467 (2)C31—C321.452 (3)
N7—C91.471 (2)C32—C331.367 (3)
N7—C171.485 (2)C33—C341.386 (3)
N8—C261.461 (3)C33—H33A0.9500
N9—C281.451 (3)C34—C351.393 (3)
N10—C301.459 (3)C35—C361.357 (3)
N11—C321.453 (3)C35—H35A0.9500
N12—C341.445 (3)C37—C421.450 (3)
N13—C361.457 (3)C37—C381.453 (3)
N14—C381.451 (3)C38—C391.369 (3)
N15—C401.442 (3)C39—C401.383 (3)
N16—C421.452 (3)C39—H39A0.9500
N18—C451.139 (3)C40—C411.383 (3)
N17—C431.135 (3)C41—C421.366 (3)
C1—C61.388 (3)C41—H41A0.9500
C1—C21.392 (3)C43—C441.446 (3)
C2—C31.380 (3)C44—H44A0.9800
C2—H2B0.9500C44—H44B0.9800
C3—C41.393 (4)C44—H44C0.9800
C3—H3B0.9500C45—C461.437 (4)
C4—C51.389 (3)C46—H46A0.9800
C4—H4B0.9500C46—H46B0.9800
C5—C61.390 (3)C46—H46C0.9800
C7—N1—C1108.92 (16)C15—C16—N3131.52 (19)
C7—N1—H1A125.5C15—C16—C11121.77 (18)
C1—N1—H1A125.5N3—C16—C11106.72 (17)
C7—N2—C6108.99 (16)N7—C17—C18111.47 (15)
C7—N2—H2A125.5N7—C17—H17A109.3
C6—N2—H2A125.5C18—C17—H17A109.3
C10—N3—C16108.85 (16)N7—C17—H17B109.3
C10—N3—H3A125.6C18—C17—H17B109.3
C16—N3—H3A125.6H17A—C17—H17B108.0
C10—N4—C11109.27 (16)N6—C18—N5109.41 (16)
C10—N4—H4A125.4N6—C18—C17124.92 (18)
C11—N4—H4A125.4N5—C18—C17125.54 (17)
C18—N5—C24109.02 (16)C24—C19—N6106.44 (17)
C18—N5—H5A125.5C24—C19—C20121.51 (18)
C24—N5—H5A125.5N6—C19—C20132.01 (18)
C18—N6—C19108.98 (16)C21—C20—C19115.8 (2)
C18—N6—H6A125.5C21—C20—H20A122.1
C19—N6—H6A125.5C19—C20—H20A122.1
C8—N7—C9110.46 (15)C20—C21—C22122.3 (2)
C8—N7—C17112.55 (15)C20—C21—H21A118.8
C9—N7—C17108.15 (15)C22—C21—H21A118.8
O2—N8—O3120.98 (19)C23—C22—C21122.1 (2)
O2—N8—C26120.79 (17)C23—C22—H22A118.9
O3—N8—C26118.13 (17)C21—C22—H22A118.9
O4—N9—O5123.34 (18)C22—C23—C24116.0 (2)
O4—N9—C28118.64 (17)C22—C23—H23A122.0
O5—N9—C28118.02 (17)C24—C23—H23A122.0
O6—N10—O7123.04 (17)C23—C24—C19122.25 (19)
O6—N10—C30118.43 (17)C23—C24—N5131.61 (19)
O7—N10—C30118.48 (16)C19—C24—N5106.12 (17)
O9—N11—O10122.66 (17)O1—C25—C26124.49 (18)
O9—N11—C32118.81 (17)O1—C25—C30123.50 (18)
O10—N11—C32118.51 (17)C26—C25—C30112.01 (17)
O12—N12—O11123.1 (2)C27—C26—C25123.59 (18)
O12—N12—C34119.0 (2)C27—C26—N8115.42 (17)
O11—N12—C34117.9 (2)C25—C26—N8120.93 (17)
O14—N13—O13123.36 (18)C28—C27—C26119.60 (18)
O14—N13—C36118.97 (16)C28—C27—H27A120.2
O13—N13—C36117.64 (17)C26—C27—H27A120.2
O16—N14—O17121.47 (18)C27—C28—C29121.43 (18)
O16—N14—C38120.31 (17)C27—C28—N9118.90 (18)
O17—N14—C38118.22 (18)C29—C28—N9119.60 (18)
O18—N15—O19123.1 (2)C30—C29—C28118.48 (18)
O18—N15—C40119.1 (2)C30—C29—H29A120.8
O19—N15—C40117.8 (2)C28—C29—H29A120.8
O21—N16—O20122.63 (17)C29—C30—C25124.84 (18)
O21—N16—C42119.46 (17)C29—C30—N10115.98 (17)
O20—N16—C42117.90 (17)C25—C30—N10119.15 (17)
C6—C1—N1106.17 (17)O8—C31—C36124.85 (18)
C6—C1—C2121.96 (19)O8—C31—C32123.78 (18)
N1—C1—C2131.86 (19)C36—C31—C32111.21 (17)
C3—C2—C1116.1 (2)C33—C32—C31124.46 (18)
C3—C2—H2B121.9C33—C32—N11116.66 (18)
C1—C2—H2B121.9C31—C32—N11118.89 (17)
C2—C3—C4122.2 (2)C32—C33—C34119.12 (19)
C2—C3—H3B118.9C32—C33—H33A120.4
C4—C3—H3B118.9C34—C33—H33A120.4
C5—C4—C3121.7 (2)C33—C34—C35121.02 (19)
C5—C4—H4B119.2C33—C34—N12119.27 (19)
C3—C4—H4B119.2C35—C34—N12119.60 (19)
C4—C5—C6116.2 (2)C36—C35—C34118.66 (19)
C4—C5—H5B121.9C36—C35—H35A120.7
C6—C5—H5B121.9C34—C35—H35A120.7
C1—C6—N2106.46 (17)C35—C36—C31125.44 (19)
C1—C6—C5121.80 (19)C35—C36—N13117.15 (18)
N2—C6—C5131.72 (19)C31—C36—N13117.40 (18)
N2—C7—N1109.46 (16)O15—C37—C42122.38 (19)
N2—C7—C8124.27 (17)O15—C37—C38125.31 (19)
N1—C7—C8126.27 (17)C42—C37—C38112.23 (17)
N7—C8—C7111.74 (16)C39—C38—N14116.76 (18)
N7—C8—H8A109.3C39—C38—C37123.26 (19)
C7—C8—H8A109.3N14—C38—C37119.98 (18)
N7—C8—H8B109.3C38—C39—C40119.9 (2)
C7—C8—H8B109.3C38—C39—H39A120.1
H8A—C8—H8B107.9C40—C39—H39A120.1
N7—C9—C10109.82 (15)C41—C40—C39120.9 (2)
N7—C9—H9A109.7C41—C40—N15119.4 (2)
C10—C9—H9A109.7C39—C40—N15119.7 (2)
N7—C9—H9B109.7C42—C41—C40119.4 (2)
C10—C9—H9B109.7C42—C41—H41A120.3
H9A—C9—H9B108.2C40—C41—H41A120.3
N4—C10—N3109.49 (17)C41—C42—C37123.93 (19)
N4—C10—C9126.45 (17)C41—C42—N16116.95 (18)
N3—C10—C9123.92 (17)C37—C42—N16119.10 (17)
C16—C11—N4105.67 (16)N17—C43—C44179.4 (3)
C16—C11—C12122.08 (19)C43—C44—H44A109.5
N4—C11—C12132.25 (19)C43—C44—H44B109.5
C13—C12—C11115.63 (19)H44A—C44—H44B109.5
C13—C12—H12A122.2C43—C44—H44C109.5
C11—C12—H12A122.2H44A—C44—H44C109.5
C12—C13—C14122.3 (2)H44B—C44—H44C109.5
C12—C13—H13A118.8N18—C45—C46177.5 (3)
C14—C13—H13A118.8C45—C46—H46A109.5
C15—C14—C13121.6 (2)C45—C46—H46B109.5
C15—C14—H14A119.2H46A—C46—H46B109.5
C13—C14—H14A119.2C45—C46—H46C109.5
C14—C15—C16116.6 (2)H46A—C46—H46C109.5
C14—C15—H15A121.7H46B—C46—H46C109.5
C16—C15—H15A121.7
C7—N1—C1—C60.8 (2)C25—C26—C27—C280.8 (3)
C7—N1—C1—C2178.4 (2)N8—C26—C27—C28178.02 (17)
C6—C1—C2—C30.2 (3)C26—C27—C28—C290.6 (3)
N1—C1—C2—C3178.92 (19)C26—C27—C28—N9177.45 (17)
C1—C2—C3—C40.2 (3)O4—N9—C28—C2713.9 (3)
C2—C3—C4—C50.1 (4)O5—N9—C28—C27166.01 (19)
C3—C4—C5—C60.4 (3)O4—N9—C28—C29169.14 (19)
N1—C1—C6—N20.6 (2)O5—N9—C28—C2910.9 (3)
C2—C1—C6—N2178.72 (17)C27—C28—C29—C301.0 (3)
N1—C1—C6—C5179.45 (18)N9—C28—C29—C30175.83 (17)
C2—C1—C6—C50.2 (3)C28—C29—C30—C252.6 (3)
C7—N2—C6—C10.1 (2)C28—C29—C30—N10175.52 (17)
C7—N2—C6—C5178.8 (2)O1—C25—C30—C29177.11 (18)
C4—C5—C6—C10.4 (3)C26—C25—C30—C292.3 (3)
C4—C5—C6—N2178.1 (2)O1—C25—C30—N104.8 (3)
C6—N2—C7—N10.4 (2)C26—C25—C30—N10175.78 (16)
C6—N2—C7—C8179.19 (17)O6—N10—C30—C2929.4 (3)
C1—N1—C7—N20.8 (2)O7—N10—C30—C29148.04 (18)
C1—N1—C7—C8178.82 (17)O6—N10—C30—C25152.36 (18)
C9—N7—C8—C7153.47 (16)O7—N10—C30—C2530.2 (3)
C17—N7—C8—C785.54 (19)O8—C31—C32—C33172.20 (18)
N2—C7—C8—N7161.60 (16)C36—C31—C32—C333.4 (3)
N1—C7—C8—N717.9 (3)O8—C31—C32—N118.4 (3)
C8—N7—C9—C10152.31 (16)C36—C31—C32—N11176.04 (16)
C17—N7—C9—C1084.12 (19)O9—N11—C32—C33145.85 (18)
C11—N4—C10—N30.2 (2)O10—N11—C32—C3332.6 (2)
C11—N4—C10—C9175.74 (17)O9—N11—C32—C3133.6 (2)
C16—N3—C10—N40.3 (2)O10—N11—C32—C31147.96 (17)
C16—N3—C10—C9175.73 (17)C31—C32—C33—C342.9 (3)
N7—C9—C10—N4156.56 (17)N11—C32—C33—C34176.53 (17)
N7—C9—C10—N328.1 (2)C32—C33—C34—C351.6 (3)
C10—N4—C11—C160.0 (2)C32—C33—C34—N12174.76 (18)
C10—N4—C11—C12179.49 (19)O12—N12—C34—C33175.1 (2)
C16—C11—C12—C130.5 (3)O11—N12—C34—C333.3 (3)
N4—C11—C12—C13178.98 (19)O12—N12—C34—C351.3 (3)
C11—C12—C13—C141.1 (3)O11—N12—C34—C35179.7 (2)
C12—C13—C14—C150.8 (3)C33—C34—C35—C361.1 (3)
C13—C14—C15—C160.3 (3)N12—C34—C35—C36175.22 (18)
C14—C15—C16—N3179.0 (2)C34—C35—C36—C312.0 (3)
C14—C15—C16—C110.9 (3)C34—C35—C36—N13179.36 (17)
C10—N3—C16—C15179.8 (2)O8—C31—C36—C35172.61 (19)
C10—N3—C16—C110.3 (2)C32—C31—C36—C352.9 (3)
N4—C11—C16—C15179.87 (17)O8—C31—C36—N136.1 (3)
C12—C11—C16—C150.5 (3)C32—C31—C36—N13178.39 (16)
N4—C11—C16—N30.2 (2)O14—N13—C36—C35142.79 (19)
C12—C11—C16—N3179.38 (17)O13—N13—C36—C3535.4 (3)
C8—N7—C17—C1866.3 (2)O14—N13—C36—C3138.4 (2)
C9—N7—C17—C18171.37 (16)O13—N13—C36—C31143.43 (18)
C19—N6—C18—N51.6 (2)O16—N14—C38—C39172.89 (18)
C19—N6—C18—C17174.45 (17)O17—N14—C38—C397.9 (3)
C24—N5—C18—N61.8 (2)O16—N14—C38—C376.8 (3)
C24—N5—C18—C17174.16 (17)O17—N14—C38—C37172.39 (17)
N7—C17—C18—N698.3 (2)O15—C37—C38—C39170.2 (2)
N7—C17—C18—N577.0 (2)C42—C37—C38—C396.5 (3)
C18—N6—C19—C240.7 (2)O15—C37—C38—N149.4 (3)
C18—N6—C19—C20177.0 (2)C42—C37—C38—N14173.81 (16)
C24—C19—C20—C210.1 (3)N14—C38—C39—C40178.44 (17)
N6—C19—C20—C21177.5 (2)C37—C38—C39—C401.9 (3)
C19—C20—C21—C220.2 (3)C38—C39—C40—C412.1 (3)
C20—C21—C22—C230.6 (3)C38—C39—C40—N15179.58 (18)
C21—C22—C23—C240.5 (3)O18—N15—C40—C41175.1 (2)
C22—C23—C24—C190.1 (3)O19—N15—C40—C415.0 (3)
C22—C23—C24—N5178.2 (2)O18—N15—C40—C392.5 (3)
N6—C19—C24—C23178.12 (17)O19—N15—C40—C39177.5 (2)
C20—C19—C24—C230.2 (3)C39—C40—C41—C420.6 (3)
N6—C19—C24—N50.4 (2)N15—C40—C41—C42178.11 (19)
C20—C19—C24—N5178.35 (17)C40—C41—C42—C375.0 (3)
C18—N5—C24—C23177.0 (2)C40—C41—C42—N16176.66 (17)
C18—N5—C24—C191.3 (2)O15—C37—C42—C41168.7 (2)
O1—C25—C26—C27178.83 (18)C38—C37—C42—C418.1 (3)
C30—C25—C26—C270.6 (3)O15—C37—C42—N169.6 (3)
O1—C25—C26—N84.1 (3)C38—C37—C42—N16173.53 (16)
C30—C25—C26—N8176.56 (16)O21—N16—C42—C41153.01 (18)
O2—N8—C26—C27179.8 (2)O20—N16—C42—C4125.9 (2)
O3—N8—C26—C273.8 (3)O21—N16—C42—C3728.5 (3)
O2—N8—C26—C252.9 (3)O20—N16—C42—C37152.55 (17)
O3—N8—C26—C25173.5 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O10.881.962.834 (2)173
N2—H2A···O15i0.881.882.619 (2)140
N2—H2A···O16i0.882.272.952 (2)134
N3—H3A···O10.882.012.847 (2)158
N3—H3A···O70.882.332.905 (2)123
N4—H4A···N17ii0.882.182.965 (3)148
N5—H5A···O10.882.282.836 (2)121
N5—H5A···O20.882.092.853 (2)144
N6—H6A···O8iii0.881.912.693 (2)147
N6—H6A···O14iii0.882.302.945 (2)130
Symmetry codes: (i) x+1, y+2, z+1; (ii) x+1, y+2, z; (iii) x, y+1, z.

Experimental details

Crystal data
Chemical formulaC24H24N73+·3C6H2N3O7·2C2H3N
Mr1176.93
Crystal system, space groupTriclinic, P1
Temperature (K)153
a, b, c (Å)10.9914 (3), 15.4620 (5), 16.1760 (6)
α, β, γ (°)74.826 (1), 74.337 (1), 73.299 (1)
V3)2484.29 (14)
Z2
Radiation typeMo Kα
µ (mm1)0.13
Crystal size (mm)0.38 × 0.36 × 0.30
Data collection
DiffractometerBruker APEXII CCD
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
18903, 8608, 6896
Rint0.016
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.037, 0.127, 1.14
No. of reflections8608
No. of parameters769
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.60, 0.52

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O10.881.962.834 (2)173
N2—H2A···O15i0.881.882.619 (2)140
N2—H2A···O16i0.882.272.952 (2)134
N3—H3A···O10.882.012.847 (2)158
N3—H3A···O70.882.332.905 (2)123
N4—H4A···N17ii0.882.182.965 (3)148
N5—H5A···O10.882.282.836 (2)121
N5—H5A···O20.882.092.853 (2)144
N6—H6A···O8iii0.881.912.693 (2)147
N6—H6A···O14iii0.882.302.945 (2)130
Symmetry codes: (i) x+1, y+2, z+1; (ii) x+1, y+2, z; (iii) x, y+1, z.
 

Acknowledgements

The authors acknowledge financial support and a grant from the 'Qing Lan' Talent Engineering Funds and Students' Science and Technology Innovation Funds (grant No. DXS2010–040) in Lanzhou Jiaotong University. A grant from the Middle-Young Age Science Foundation (grant No. 3YS061-A25–023) and the Long Yuan 'Qing Nian' of Gansu Province is also acknowledged.

References

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