organic papers
o1344
Zhuet al. C18H15N63+3NO3 doi:10.1107/S160053680604431X Acta Cryst.(2007). E63, o1344–o1346
Acta Crystallographica Section E
Structure Reports
Online
ISSN 1600-5368
4,4
000,4
000000-(1,3,5-Triazine-2,4,6-triyl)tripyridinium
trinitrate
Shou-Rong Zhu,a* Wan-Dong Chen,b Hong-Jian Zhao,aMin Shaocand Ming-Xing Lia
aDepartment of Chemistry, College of Science,
Shanghai University, Shanghai 200444, People’s Republic of China,bDepartment of Chemistry,
Jining Teachers’ College, Qufu 273100, People’s Republic of China, andcInstrumental
Analysis and Research Center, Shanghai University, Shanghai 200444, People’s Republic of China
Correspondence e-mail: [email protected]
Key indicators
Single-crystal X-ray study
T= 273 K
Mean(C–C) = 0.003 A˚
Rfactor = 0.033
wRfactor = 0.082 Data-to-parameter ratio = 6.8
For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e.
Received 6 September 2006 Accepted 23 October 2006
#2007 International Union of Crystallography
All rights reserved
Reaction of 2,4,6-tris(4-pyridyl)-1,3,5-triazine (tpt) with excess nitric acid in an aqueous solution affords the title compound, C18H15N6
3+ 3NO3
. The torsion angles between adjacent aromatic rings are much larger than those of neutral tpt. All three pyridine N atoms are protonated.
Comment
The trigonal tridentate ligand 2,4,6-tris(4-pyridyl)-1,3,5-tria-zine has been of special interest in recent years (Fujitaet al., 2005). Tpt is anexo-tridentate ligand; the N atoms of the three pyridyl groups can bind only to different metal atoms. Its rigidity and triangular geometry can lead to the formation of porous frameworks enclosing nanoporous cages (Yoshizawaet al.2004; Kusukawa & Fujita, 2002), cavities (Sunet al., 2002; Yoshizawa et al., 2005), chambers (Batten et al., 1995) and channels (Ohmoriet al., 2005). The crystal structure of neutral tpt was reported previously by Janczaket al.(2003). We report here the crystal structure of its nitrate salt, (I).
As shown in Fig. 1, the three 4-pyridyl rings bind to the triazine ring through atoms C1, C2 and C3. There are three NO3
[image:1.610.256.406.398.543.2]
ions in the structure. In neutral tpt, all four six-membered rings are essentially coplanar, with a maximum torsion angle of 7.44 (10)(Janczaket al., 2003), while in (I), the torsion angles between adjacent aromatic rings vary from 7.5 (3) to 14.8 (2), somewhat larger than in tpt. C—N distances of 1.339–1.344 A˚ are observed in the triazine rings and 1.332–1.337 A˚ in the pyridine rings in tpt. The triazine C— N distances of 1.329 (3)–1.339 (3) A˚ in the title compound are slightly shorter than in tpt, thus ruling out the possibility of the triazine ring being protonated. The C—N distances of 1.327 (3)–1.340 (3) A˚ in the pyridine rings in (I) are essentially the same as in tpt.
a well defined layer form through–interaction; the distance between layers is 3.317 A˚ . In (I), the distorted H3tpt3+ and
nitrate groups link different layers through hydrogen bonding. The inter-layer distance is 3.298 A˚ in (I), which is slightly shorter than that in tpt. The hydrogen-bonding distances and
angles are listed in Table 1. Clearly, there are hydrogen-bond interactions between pyridine N and nitrate O atoms, which further indicate that the H atoms bind to pyridine N atoms rather than triazine N atoms.
Experimental
The title compound was prepared by adding solid tpt (31 mg, 0.1 mmol) to a 50 ml beaker containing 10 ml of water and two drops of concentrated HNO3. The mixture was warmed to give a clear
solution and then filtered to remove impurities. The mixture was allowed to stand for several days at room temperature. X-ray diffraction quality crystals of (I) formed in 60% yield.
Crystal data
C18H15N63+3NO3
Mr= 501.39
Monoclinic,Cc a= 9.8940 (12) A˚ b= 21.637 (3) A˚ c= 9.9734 (12) A˚ = 109.671 (1)
V= 2010.4 (4) A˚3
Z= 4
MoKradiation = 0.14 mm1
T= 273 (2) K 0.400.200.20 mm
Data collection
Bruker APEX-II area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) Tmin= 0.948,Tmax= 0.973
6240 measured reflections 2300 independent reflections 2078 reflections withI> 2(I) Rint= 0.021
Refinement
R[F2> 2(F2)] = 0.033
wR(F2) = 0.082
S= 1.05 2300 reflections 338 parameters
H atoms treated by a mixture of independent and constrained refinement
max= 0.21 e A˚
3
min=0.21 e A˚
3
Table 1
Hydrogen-bond geometry (A˚ ,).
D—H A D—H H A D A D—H A
N6—H6A O4i 0.90 (3) 2.43 (3) 2.984 (3) 120 (3) N5—H5A O9ii
0.93 (4) 1.92 (4) 2.826 (3) 165 (3) N4—H4A O8iii
0.85 (4) 2.54 (4) 3.095 (3) 124 (3) N4—H4A O6iv
0.85 (4) 2.18 (4) 2.917 (3) 145 (4)
Symmetry codes: (i)x;yþ2;z1 2; (ii)xþ
1 2;yþ
1
2;z1; (iii)xþ1;yþ1;zþ 1 2; (iv) xþ1
2;yþ 3 2;zþ
1 2.
The pyridinium H atoms were located in a difference Fourier map and refined freely (distances are in Table 1). The aromatic H atoms were constrained to ride on their parent C atoms, with a distance of 0.93 A˚ andUiso(H) = 1.2Ueq(C). In the absence of significant
anom-alous scattering, Friedel pairs have been averaged.
Data collection:APEX2(Bruker, 2000); cell refinement:SAINT
(Bruker, 2000); data reduction:SAINT; program(s) used to solve structure:SHELXS97(Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics:
SHELXTL(Sheldrick, 2000); software used to prepare material for publication:SHELXTL.
The project was supported by the Development Foundation
of Shanghai Municipal Education Commission, China.
organic papers
Acta Cryst.(2007). E63, o1344–o1346 Zhuet al. C
[image:2.610.57.276.69.341.2] [image:2.610.48.295.376.652.2]18H15N63+3NO3
o1345
Figure 1
The structure of the constituent ions of (I), with displacement ellipsoids drawn at the 30% probability level.
Figure 2
Professor Weng Lin-Hong (Fudan University) is kindly acknowledged for assistance with the CIF.
References
Batten, S. R., Hoskins, B. F. & Robson, R. (1995).J. Am. Chem. Soc.117, 5385– 5386.
Bruker (2000).APEX2andSAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Fujita, M., Tominaga, M., Hori, A. & Therrien, B. (2005).Acc. Chem. Res.38, 371–380.
Janczak, J., S´ledz´, M. & Kubiak, R. (2003). J. Mol. Struct. 659, 71– 79.
Kusukawa, T. & Fujita, M. (2002).J. Am. Chem. Soc.124, 13576–13582. Ohmori, O., Kawano, M. & Fujita, M. (2005).Angew. Chem. Int. Ed.44, 1962–
1964.
Sheldrick, G. M. (1996).SADABS. University of Go¨ttingen, Germany. Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of
Go¨ttingen, Germany.
Sheldrick, G. M. (2000).SHELXTL. Version 6.1. Bruker AXS Inc., Madison, Wisconsin, USA.
Sun, W. Y., Kusukawa, T. & Fujita, M. (2002).J. Am. Chem. Soc.124, 11570– 11571.
Yoshizawa, M., Miyagi, S., Kawano, M., Ishiguro, K. & Fujita, M. (2004).J. Am. Chem. Soc.126, 9172–9173.
Yoshizawa, M., Nakagawa, J., Kumazawa, K., Nagao, M., Kawano, M., Ozeki, T. & Fujita, M. (2005).Angew. Chem. Int. Ed.44, 1810–1813.
organic papers
o1346
Zhuet al. Csupporting information
sup-1
Acta Cryst. (2007). E63, o1344–o1346
supporting information
Acta Cryst. (2007). E63, o1344–o1346 [https://doi.org/10.1107/S160053680604431X]
4,4
′
,4
′′
-(1,3,5-Triazine-2,4,6-triyl)tripyridinium trinitrate
Shou-Rong Zhu, Wan-Dong Chen, Hong-Jian Zhao, Min Shao and Ming-Xing Li
4,4′,4′′-(1,3,5-Triazine-2,4,6-triyl)tripyridinium trinitrate
Crystal data
C18H15N63+·3NO3− Mr = 501.39 Monoclinic, Cc a = 9.8940 (12) Å
b = 21.637 (3) Å
c = 9.9734 (12) Å
β = 109.671 (1)°
V = 2010.4 (4) Å3 Z = 4
F(000) = 1032
Dx = 1.657 Mg m−3
Mo Kα radiation, λ = 0.71073 Å Cell parameters from 2778 reflections
θ = 2.4–27.1°
µ = 0.14 mm−1 T = 273 K
Rhomb, pale_brown 0.40 × 0.20 × 0.20 mm
Data collection
Bruker APEX-II area-detector diffractometer
Radiation source: fine-focus sealed tube Graphite monochromator
ω scans
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)
Tmin = 0.948, Tmax = 0.973
6240 measured reflections 2300 independent reflections 2078 reflections with I > 2σ(I)
Rint = 0.021
θmax = 27.5°, θmin = 2.4° h = −11→12
k = −28→27
l = −12→12
Refinement
Refinement on F2 Least-squares matrix: full
R[F2 > 2σ(F2)] = 0.033 wR(F2) = 0.082 S = 1.05 2300 reflections 338 parameters 2 restraints
Primary atom site location: structure-invariant direct methods
Secondary atom site location: difference Fourier map
Hydrogen site location: inferred from neighbouring sites
H atoms treated by a mixture of independent and constrained refinement
w = 1/[σ2(F
o2) + (0.0501P)2 + 0.2046P] where P = (Fo2 + 2Fc2)/3
(Δ/σ)max < 0.001 Δρmax = 0.21 e Å−3 Δρmin = −0.21 e Å−3
Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 Extinction coefficient: 0.0040 (6)
Special details
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
supporting information
sup-2
Acta Cryst. (2007). E63, o1344–o1346
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)
x y z Uiso*/Ueq
C1 0.7969 (2) 0.76683 (10) 0.0970 (2) 0.0245 (5)
C2 0.7684 (2) 0.86961 (10) 0.0974 (2) 0.0244 (5)
C3 0.8598 (2) 0.81840 (10) 0.3040 (2) 0.0240 (5)
C4 0.9157 (3) 0.81854 (10) 0.4621 (2) 0.0243 (5)
C5 0.9556 (3) 0.87405 (10) 0.5364 (2) 0.0287 (5)
H5 0.9484 0.9112 0.4876 0.034*
C6 1.0056 (3) 0.87302 (13) 0.6829 (3) 0.0357 (6)
H6 1.0329 0.9095 0.7342 0.043*
C7 0.9785 (3) 0.76513 (12) 0.6828 (3) 0.0361 (6)
H7 0.9869 0.7288 0.7347 0.043*
C8 0.9289 (3) 0.76342 (11) 0.5362 (3) 0.0314 (5)
H8 0.9047 0.7261 0.4880 0.038*
C9 0.7775 (2) 0.70777 (10) 0.0144 (2) 0.0236 (5)
C10 0.7965 (3) 0.65085 (10) 0.0827 (3) 0.0303 (5)
H10 0.8307 0.6484 0.1816 0.036*
C11 0.7637 (3) 0.59791 (11) 0.0007 (3) 0.0358 (6)
H11 0.7726 0.5594 0.0441 0.043*
C12 0.7053 (3) 0.65594 (12) −0.2084 (3) 0.0381 (6)
H12 0.6767 0.6568 −0.3073 0.046*
C13 0.7330 (3) 0.71033 (11) −0.1331 (3) 0.0312 (5)
H13 0.7222 0.7481 −0.1800 0.037*
C14 0.7142 (3) 0.92783 (9) 0.0180 (2) 0.0259 (5)
C15 0.6278 (3) 0.92505 (11) −0.1242 (3) 0.0341 (6)
H15 0.6087 0.8874 −0.1720 0.041*
C16 0.5708 (3) 0.97917 (13) −0.1930 (3) 0.0403 (6)
H16 0.5123 0.9783 −0.2881 0.048*
C17 0.6828 (3) 1.03675 (11) 0.0123 (3) 0.0367 (6)
H17 0.6997 1.0751 0.0570 0.044*
C18 0.7437 (3) 0.98466 (10) 0.0863 (3) 0.0308 (5)
H18 0.8038 0.9873 0.1807 0.037*
H4A 1.048 (4) 0.8167 (18) 0.841 (5) 0.071 (12)*
H5A 0.696 (4) 0.5691 (17) −0.204 (4) 0.062 (10)*
H6A 0.558 (4) 1.0645 (15) −0.179 (3) 0.047 (9)*
N1 0.8492 (2) 0.76378 (8) 0.2383 (2) 0.0264 (4)
N2 0.7533 (2) 0.81794 (8) 0.0208 (2) 0.0266 (4)
N3 0.8226 (2) 0.87272 (8) 0.23940 (19) 0.0263 (4)
N4 1.0145 (3) 0.81930 (11) 0.7506 (2) 0.0386 (5)
N5 0.7191 (3) 0.60213 (10) −0.1409 (3) 0.0381 (5)
N6 0.5996 (3) 1.03253 (10) −0.1234 (3) 0.0387 (5)
supporting information
sup-3
Acta Cryst. (2007). E63, o1344–o1346
N8 0.6079 (2) 0.80094 (9) 0.5292 (2) 0.0297 (4)
N9 0.0472 (3) 0.04132 (9) 0.5145 (2) 0.0331 (4)
O1 0.3186 (3) 0.87619 (10) −0.0780 (2) 0.0583 (6)
O2 0.3768 (2) 0.96804 (9) 0.0031 (2) 0.0492 (5)
O3 0.4505 (3) 0.88892 (9) 0.1404 (2) 0.0573 (6)
O4 0.5819 (3) 0.83154 (9) 0.4186 (2) 0.0490 (6)
O5 0.6594 (3) 0.82693 (8) 0.6469 (2) 0.0498 (6)
O6 0.5829 (2) 0.74439 (8) 0.5232 (2) 0.0428 (5)
O7 0.0043 (3) 0.00839 (9) 0.4068 (2) 0.0511 (6)
O8 0.0252 (3) 0.09767 (8) 0.5067 (2) 0.0505 (5)
O9 0.1116 (3) 0.01682 (9) 0.6336 (2) 0.0508 (6)
Atomic displacement parameters (Å2)
U11 U22 U33 U12 U13 U23
C1 0.0300 (11) 0.0189 (10) 0.0229 (11) 0.0003 (9) 0.0066 (9) −0.0023 (9)
C2 0.0303 (12) 0.0190 (10) 0.0222 (11) 0.0022 (9) 0.0068 (9) 0.0011 (8)
C3 0.0291 (12) 0.0204 (11) 0.0214 (11) −0.0009 (9) 0.0071 (9) 0.0002 (8)
C4 0.0272 (11) 0.0237 (11) 0.0190 (11) 0.0024 (9) 0.0037 (9) 0.0011 (9)
C5 0.0344 (13) 0.0249 (11) 0.0230 (12) 0.0003 (10) 0.0047 (10) −0.0002 (9)
C6 0.0415 (14) 0.0370 (13) 0.0238 (12) −0.0026 (11) 0.0045 (10) −0.0059 (10)
C7 0.0450 (15) 0.0343 (13) 0.0260 (13) 0.0060 (12) 0.0080 (11) 0.0099 (10)
C8 0.0408 (14) 0.0244 (11) 0.0264 (13) 0.0002 (10) 0.0079 (11) 0.0015 (10)
C9 0.0280 (11) 0.0182 (10) 0.0222 (11) 0.0016 (8) 0.0053 (9) −0.0021 (8)
C10 0.0364 (13) 0.0212 (11) 0.0307 (13) 0.0028 (10) 0.0080 (10) 0.0011 (10)
C11 0.0421 (14) 0.0189 (11) 0.0440 (16) 0.0038 (10) 0.0113 (12) −0.0018 (10)
C12 0.0493 (16) 0.0324 (13) 0.0278 (14) 0.0005 (11) 0.0067 (12) −0.0086 (10)
C13 0.0410 (13) 0.0236 (11) 0.0260 (13) 0.0011 (10) 0.0073 (10) −0.0026 (9)
C14 0.0348 (12) 0.0210 (10) 0.0214 (11) 0.0029 (9) 0.0089 (9) 0.0021 (9)
C15 0.0470 (14) 0.0306 (12) 0.0224 (12) 0.0074 (11) 0.0088 (11) 0.0018 (9)
C16 0.0495 (16) 0.0433 (15) 0.0251 (14) 0.0124 (12) 0.0085 (12) 0.0126 (11)
C17 0.0429 (15) 0.0226 (11) 0.0465 (16) 0.0028 (10) 0.0174 (13) 0.0049 (11)
C18 0.0376 (13) 0.0214 (11) 0.0313 (14) 0.0009 (10) 0.0090 (11) 0.0003 (9)
N1 0.0367 (11) 0.0204 (9) 0.0187 (9) 0.0007 (8) 0.0047 (8) 0.0007 (7)
N2 0.0367 (11) 0.0193 (9) 0.0193 (10) 0.0007 (8) 0.0036 (8) −0.0006 (7)
N3 0.0365 (11) 0.0207 (9) 0.0185 (10) −0.0008 (8) 0.0049 (8) 0.0003 (7)
N4 0.0451 (13) 0.0503 (14) 0.0158 (10) 0.0010 (11) 0.0040 (9) 0.0009 (10)
N5 0.0437 (13) 0.0259 (11) 0.0412 (14) −0.0013 (9) 0.0097 (10) −0.0135 (10)
N6 0.0446 (13) 0.0279 (11) 0.0464 (15) 0.0130 (10) 0.0190 (11) 0.0182 (10)
N7 0.0388 (11) 0.0260 (10) 0.0328 (11) −0.0023 (9) 0.0098 (9) −0.0065 (9)
N8 0.0375 (11) 0.0252 (9) 0.0237 (10) −0.0018 (9) 0.0069 (8) −0.0034 (8)
N9 0.0453 (12) 0.0257 (9) 0.0277 (10) −0.0055 (9) 0.0116 (9) −0.0041 (9)
O1 0.0785 (16) 0.0408 (11) 0.0368 (12) −0.0042 (11) −0.0056 (11) −0.0105 (9)
O2 0.0620 (13) 0.0272 (9) 0.0537 (14) 0.0045 (9) 0.0134 (10) −0.0009 (9)
O3 0.0818 (17) 0.0391 (11) 0.0328 (12) −0.0066 (11) −0.0048 (11) 0.0016 (9)
O4 0.0817 (16) 0.0318 (10) 0.0225 (10) −0.0141 (9) 0.0032 (9) 0.0024 (7)
O5 0.0841 (16) 0.0344 (10) 0.0239 (10) −0.0056 (10) 0.0087 (10) −0.0085 (8)
supporting information
sup-4
Acta Cryst. (2007). E63, o1344–o1346
O7 0.0789 (16) 0.0358 (10) 0.0295 (11) −0.0085 (10) 0.0065 (10) −0.0098 (8)
O8 0.0728 (15) 0.0285 (9) 0.0422 (11) 0.0018 (9) 0.0087 (10) −0.0029 (9)
O9 0.0856 (16) 0.0334 (10) 0.0256 (10) −0.0018 (10) 0.0083 (10) −0.0008 (8)
Geometric parameters (Å, º)
C1—N2 1.329 (3) C12—C13 1.373 (3)
C1—N1 1.329 (3) C12—H12 0.930
C1—C9 1.497 (3) C13—H13 0.930
C2—N2 1.334 (3) C14—C18 1.388 (3)
C2—N3 1.336 (3) C14—C15 1.390 (3)
C2—C14 1.488 (3) C15—C16 1.378 (3)
C3—N3 1.331 (3) C15—H15 0.930
C3—N1 1.338 (3) C16—N6 1.328 (4)
C3—C4 1.485 (3) C16—H16 0.930
C4—C8 1.386 (3) C17—N6 1.329 (4)
C4—C5 1.397 (3) C17—C18 1.371 (3)
C5—C6 1.376 (3) C17—H17 0.930
C5—H5 0.930 C18—H18 0.930
C6—N4 1.332 (4) N4—H4A 0.85 (4)
C6—H6 0.930 N5—H5A 0.93 (4)
C7—N4 1.340 (4) N6—H6A 0.90 (3)
C7—C8 1.377 (4) N7—O1 1.233 (3)
C7—H7 0.930 N7—O2 1.241 (3)
C8—H8 0.930 N7—O3 1.254 (3)
C9—C13 1.387 (3) N8—O4 1.237 (3)
C9—C10 1.389 (3) N8—O5 1.246 (3)
C10—C11 1.381 (3) N8—O6 1.245 (2)
C10—H10 0.930 N9—O8 1.236 (3)
C11—N5 1.333 (4) N9—O7 1.239 (3)
C11—H11 0.930 N9—O9 1.260 (3)
C12—N5 1.328 (3)
N2—C1—N1 125.68 (19) C9—C13—H13 120.7
N2—C1—C9 116.02 (19) C18—C14—C15 119.7 (2)
N1—C1—C9 118.22 (19) C18—C14—C2 120.7 (2)
N2—C2—N3 125.23 (19) C15—C14—C2 119.6 (2)
N2—C2—C14 116.98 (19) C16—C15—C14 118.6 (2)
N3—C2—C14 117.73 (18) C16—C15—H15 120.7
N3—C3—N1 125.4 (2) C14—C15—H15 120.7
N3—C3—C4 117.09 (19) N6—C16—C15 119.9 (3)
N1—C3—C4 117.5 (2) N6—C16—H16 120.0
C8—C4—C5 119.8 (2) C15—C16—H16 120.0
C8—C4—C3 120.0 (2) N6—C17—C18 120.1 (2)
C5—C4—C3 120.2 (2) N6—C17—H17 120.0
C6—C5—C4 119.1 (2) C18—C17—H17 120.0
C6—C5—H5 120.5 C17—C18—C14 118.8 (2)
supporting information
sup-5
Acta Cryst. (2007). E63, o1344–o1346
N4—C6—C5 119.4 (2) C14—C18—H18 120.6
N4—C6—H6 120.3 C1—N1—C3 114.44 (18)
C5—C6—H6 120.3 C1—N2—C2 114.68 (19)
N4—C7—C8 119.9 (2) C3—N3—C2 114.53 (18)
N4—C7—H7 120.1 C6—N4—C7 123.2 (2)
C8—C7—H7 120.1 C6—N4—H4A 122 (3)
C7—C8—C4 118.6 (2) C7—N4—H4A 115 (3)
C7—C8—H8 120.7 C12—N5—C11 122.5 (2)
C4—C8—H8 120.7 C12—N5—H5A 112 (2)
C13—C9—C10 119.8 (2) C11—N5—H5A 126 (2)
C13—C9—C1 119.0 (2) C16—N6—C17 122.9 (2)
C10—C9—C1 121.1 (2) C16—N6—H6A 112 (2)
C11—C10—C9 118.6 (2) C17—N6—H6A 125 (2)
C11—C10—H10 120.7 O1—N7—O2 120.7 (2)
C9—C10—H10 120.7 O1—N7—O3 119.4 (2)
N5—C11—C10 119.9 (2) O2—N7—O3 119.9 (2)
N5—C11—H11 120.1 O4—N8—O5 119.7 (2)
C10—C11—H11 120.1 O4—N8—O6 120.3 (2)
N5—C12—C13 120.4 (2) O5—N8—O6 120.0 (2)
N5—C12—H12 119.8 O8—N9—O7 120.7 (2)
C13—C12—H12 119.8 O8—N9—O9 119.8 (2)
C12—C13—C9 118.7 (2) O7—N9—O9 119.5 (2)
C12—C13—H13 120.7
Hydrogen-bond geometry (Å, º)
D—H···A D—H H···A D···A D—H···A
N6—H6A···O4i 0.90 (3) 2.43 (3) 2.984 (3) 120 (3)
N5—H5A···O9ii 0.93 (4) 1.92 (4) 2.826 (3) 165 (3)
N4—H4A···O8iii 0.85 (4) 2.54 (4) 3.095 (3) 124 (3)
N4—H4A···O6iv 0.85 (4) 2.18 (4) 2.917 (3) 145 (4)
