metal-organic papers
m878
Pulset al. (C2H10N2)(C2H9N2)2[Sn2S6] Acta Cryst.(2005). E61, m868–m870 Acta Crystallographica Section E
Structure Reports Online
ISSN 1600-5368
Bis(2-aminoethylammonium)
(ethylene-diammonium) (di-
l
-sulfido-
j
2S
:
S
)bis-[dithiostannate(IV)]
Angela Puls, Christian Na¨ther and Wolfgang Bensch*
Institut fu¨r Anorganische Chemie, Christian-Albrechts-Universita¨t Kiel, Olshausenstraße 40, D-24098 Kiel, Germany
Correspondence e-mail: cnaether@ac.uni-kiel.de
Key indicators
Single-crystal X-ray study
T= 170 K
Mean(C–C) = 0.005 A˚
Rfactor = 0.029
wRfactor = 0.076
Data-to-parameter ratio = 25.9
For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e.
#2005 International Union of Crystallography
Printed in Great Britain – all rights reserved
The crystal structure of the title compound, (C2H10N2
)-(C2H9N2)2[Sn2S6], consists of discrete [Sn2S6] 4
anions and mono- as well as diprotonated ethylenediamine molecules. The anion and the monoprotonated cation occupy general positions, whereas the dications are located on centres of inversion. In the crystal structure, the anions and cations are
connectedviaN—H S and N—H N hydrogen bonds.
Comment
In the last few years, several compounds containing the [Sn2S6]
4
anion have been reported. Examples with
proto-nated organic amines as counterions are (CHAH)2[Sn2S6]
(CHA is cyclohexylamine; Jianget al., 1998), (C12H25NH3)4
-[Sn2S6]2H2O (Li et al., 1997), (C6H20N4)2[Sn2S6]2H2O
(Na¨ther et al., 2003) and (enH)4[Sn2S6] (en =
ethylene-diamine) (Dehnen & Zimmermann, 2002). There are also some compounds containing transition metal complexes as
charge-compensating cations, e.g. [Ni(en)3]2[Sn2S6],
[Ni(dap)3]2[Sn2S6]2H2O (dap is 1,2-diaminopropane),
[Co(tren)3]2[Sn2S6] [tren is tris(2-aminoethyl)amine] and
[Ni(tren)3]2[Sn2S6] (Behrens et al., 2003), and C12H44N8O2
-[S6Sn2][M(en)3]2[Sn2S6] (Mis Mn, Co or Zn; Jiaet al., 2004).
Many of these compounds were prepared under solvothermal conditions. We are interested in the syntheses, structures and properties of thiostannates containing protonated organic amines. We now report the synthesis and crystal structure of the title novel thiostannate, (I), prepared under solvothermal conditions.
The asymmetric unit of (I) consists of one
crystal-lographically independent [Sn2S6]
4
anion, two crystal-lographically independent monoprotonated ethylenediamine ions and half each of two crystallographically independent diprotonated ethylenediammonium dications (Fig. 1). The two diprotonated cations are each located on centres of inversion, whereas the [Sn2S6]
4
anion and the two monoprotonated
cations occupy general positions. The [Sn2S6]
4
anions are
formed by two edge-sharing SnS4tetrahedra.
The Sn—S distances to the terminal S atoms range from
2.3337 (9) to 2.3509 (8) A˚ , shorter than the Sn—S bond
lengths to the bridging S atoms [2.4409 (9)–2.4868 (8) A˚ ]
(Table 1). The S—Sn—S angles in the Sn2S2ring [93.46 (3) and
94.34 (3)] are smaller than those to the terminal S atoms
[106.50 (3)–117.06 (3)]. The geometric parameters found in
the [Sn2S6] 4
anion are comparable with those in other
thio-stannates (Behrenset al., 2003).
Between the anions and cations, N—H S hydrogen bonds
are found (Fig. 2). The N S distances are in the range
3.228 (3)–3.683 (3) A˚ and the H S distances are between
2.40 and 2.83 A˚ ; the N—H S angles range from 147 to 174.
The two monoprotonated cations are also connectedviaN—
H N hydrogen bonds into dimers (Fig. 1). The two
dipro-tonated cations are each. In these dimers, each of the cations
acts as a hydrogen-bond donor and acceptor. The N N
distances are 2.833 (4) and 2.849 (5) A˚ , the H N distances
are 1.95 and 1.97 A˚ , and the N—H N angles are both 162.
We note that a thiostannate with four monoprotonated ethylenediamine molecules has been obtained using a room-temperature solvent route (Dehnen & Zimmermann, 2002).
Experimental
The title compound was prepared by the reaction of elemental Sn (275.4 mg) and S (48.2 mg) in a 20% solution of ethylenediamine in methanol (3.75 ml), in a Teflon-lined steel autoclave under solvo-thermal conditions. The reaction mixture was heated for 3 d at 433 K, tempered for 12 h at 363 K and cooled. The product was washed with water and ethanol (yield 10%, based on Sn) and was contaminated with large amounts of SnS2.
Crystal data
(C2H10N2)(C2H9N2)2[Sn2S6] Mr= 614.08
Triclinic,P1
a= 8.7638 (7) A˚
b= 10.729 (1) A˚
c= 12.222 (1) A˚
= 74.85 (1)
= 73.00 (1)
= 88.98 (1)
V= 1058.54 (16) A˚3
Z= 2
Dx= 1.927 Mg m
3
MoKradiation Cell parameters from 8000
reflections
= 2.5–28
= 2.95 mm1 T= 170 (2) K Block, colourless 0.090.090.08 mm
Data collection
Stoe IPDS-1 diffractometer
’scans
Absorption correction: none 11 088 measured reflections 4820 independent reflections 3926 reflections withI> 2(I)
Rint= 0.044
max= 28.0
h=11!11
k=14!14
l=16!16
Refinement
Refinement onF2 R[F2> 2(F2)] = 0.029 wR(F2) = 0.077 S= 0.97 4820 reflections 186 parameters
H-atom parameters constrained
w= 1/[2
(Fo2) + (0.0472P)2]
whereP= (Fo2+ 2Fc2)/3
(/)max= 0.001 max= 0.91 e A˚
3 min=1.80 e A˚ 3
Extinction correction:SHELXL97
(Sheldrick, 1997)
Extinction coefficient: 0.0039 (5)
Table 1
Selected geometric parameters (A˚ ,).
Sn1—S2 2.3337 (9)
Sn1—S1 2.3474 (8)
Sn1—S3 2.4549 (9)
Sn1—S4 2.4868 (8)
Sn2—S5 2.3434 (9)
Sn2—S6 2.3509 (8)
Sn2—S4 2.4409 (9)
Sn2—S3 2.4659 (8)
S2—Sn1—S1 117.06 (3)
S2—Sn1—S3 111.51 (3)
S1—Sn1—S3 112.48 (3)
S2—Sn1—S4 109.00 (3)
S1—Sn1—S4 110.79 (3)
S3—Sn1—S4 93.46 (3)
S5—Sn2—S6 114.80 (3)
S5—Sn2—S4 113.84 (3)
S6—Sn2—S4 112.12 (3)
S5—Sn2—S3 106.50 (3)
S6—Sn2—S3 113.35 (3)
S4—Sn2—S3 94.34 (3)
Sn1—S3—Sn2 86.14 (3)
[image:2.610.44.293.70.226.2]Sn2—S4—Sn1 85.98 (3)
Table 2
Hydrogen-bond geometry (A˚ ,).
D—H A D—H H A D A D—H A
N1—H1N1 N4 0.91 1.95 2.833 (4) 162
N1—H2N1 S2i
0.91 2.40 3.228 (3) 151
N1—H3N1 S5 0.91 2.49 3.390 (3) 168
N2—H1N2 S6ii
0.91 2.65 3.477 (3) 152
N2—H2N2 S1iii
0.91 2.83 3.683 (3) 157
N3—H1N3 N2 0.91 1.97 2.849 (5) 162
N3—H2N3 S5ii
0.91 2.36 3.271 (3) 174
N3—H3N3 S6 0.91 2.55 3.436 (4) 164
N4—H1N4 S1i
0.91 2.68 3.523 (3) 155
N4—H2N4 S2iii 0.91 2.72 3.533 (3) 150
N5—H1N5 S2iv
0.91 2.41 3.263 (3) 157
N5—H2N5 S1v
0.91 2.44 3.303 (3) 159
N5—H3N5 S6vi 0.91 2.35 3.260 (3) 174
N6—H1N6 S5 0.91 2.40 3.293 (3) 167
N6—H2N6 S6vii
0.91 2.60 3.399 (3) 147
N6—H3N6 S1iv
0.91 2.35 3.250 (3) 173
Symmetry codes: (i) xþ1;yþ1;z; (ii) x;y;zþ1; (iii) x;y1;z; (iv) xþ1;yþ1;zþ1; (v)x;y;zþ1; (vi)xþ1;y;zþ1; (vii)x;yþ1;zþ1.
All H atoms were located in difference maps. C-bound H atoms were positioned with idealized geometry, with C—H = 0.99 A˚ , and refined with fixed isotropic displacement parameters [Uiso(H) =
1.2Ueq(C)] using a riding model. The positions of the N-bound H
atoms of the tertiary amino group were idealized with N—H distances of 0.91 A˚ , and they were then refined as rigid groups allowed to rotate but not tip, withUiso(H) = 1.5Ueq(N). N-bound H
atoms of the secondary amino groups were located in difference maps, and they were refined as riding with N—H 0.91 A˚ andUiso(H)
metal-organic papers
Acta Cryst.(2005). E61, m868–m870 Pulset al. (C
2H10N2)(C2H9N2)2[Sn2S6]
m879
Figure 1 [image:2.610.314.564.461.619.2]= 1.2Ueq(N). The deepest hole in the difference map is1.80 e/A˚ 3
, located 0.78 A˚ from Sn2.
Data collection:IPDS(Stoe & Cie, 1998); cell refinement:IPDS; data reduction: IPDS; program(s) used to solve structure:
SHELXS97(Sheldrick, 1997); program(s) used to refine structure:
SHELXL97(Sheldrick, 1997); molecular graphics:XPinSHELXTL
(Bruker, 1998); software used to prepare material for publication:
CIFTABinSHELXL97.
This work was supported by the State of Schleswig– Holstein.
References
Behrens, M., Scherb, S., Na¨ther, C. & Bensch, W. (2003).Z. Anorg. Allg. Chem. 629, 1367–1373.
Bruker (1998) SHELXTL. Version 5.10. Bruker AXS Inc., Madison, Wisconsin, USA.
Dehnen, S. & Zimmermann, C. (2002).Z. Anorg. Allg. Chem.628, 2463–2469. Jiang, T., Lough, A., Ozin, G. A. & Bedard, R. L. (1998).J. Mater. Chem.8,
733–741.
Li, J., Marler, B., Kessler, H., Soulard, M. & Kallus, S. (1997).Inorg. Chem.36, 4697–4701.
Jia, D. X., Zhang, Y., Dai, J., Zhu, Q. Y. & Gu, X. M. (2004).Z. Anorg. Allg. Chem.630, 313–318.
Na¨ther, C., Scherb, S. & Bensch, W. (2003).Acta Cryst.E59, m280–m282. Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of
Go¨ttingen, Germany.
Stoe & Cie (1998).IPDS. Version 2.89. Stoe & Cie, Darmstadt, Germany.
metal-organic papers
m880
Pulset al. (C [image:3.610.315.565.71.236.2]2H10N2)(C2H9N2)2[Sn2S6] Acta Cryst.(2005). E61, m868–m870 Figure 2
The crystal structure of (I), viewed in the direction of the crystallographic
supporting information
sup-1 Acta Cryst. (2005). E61, m868–m870
supporting information
Acta Cryst. (2005). E61, m868–m870 [https://doi.org/10.1107/S1600536805010871]
Bis(2-aminoethylammonium) (ethylenediammonium) (di-
µ
-sulfido-
κ
2S
:
S
)bis[di-thiostannate(IV)]
Angela Puls, Christian N
ä
ther and Wolfgang Bensch
Bis(2-aminoethylammonium)(ethylenediammonium)(di-µ-sulfido- κ2S:S)bis[disulfidotin(IV)]
Crystal data
(C2H10N2)(C2H9N2)2[Sn2S6]
Mr = 614.08
Triclinic, P1 Hall symbol: -P 1 a = 8.7638 (7) Å b = 10.7287 (10) Å c = 12.2216 (10) Å α = 74.845 (10)° β = 72.997 (10)° γ = 88.978 (10)° V = 1058.54 (16) Å3
Z = 2 F(000) = 604 Dx = 1.927 Mg m−3
Mo Kα radiation, λ = 0.71073 Å Cell parameters from 8000 reflections θ = 2.5–28°
µ = 2.95 mm−1
T = 170 K Block, colourless 0.09 × 0.09 × 0.08 mm
Data collection Stoe IPDS-1
diffractometer
Radiation source: fine-focus sealed tube Graphite monochromator
φ scans
11088 measured reflections 4820 independent reflections
3926 reflections with I > 2σ(I) Rint = 0.044
θmax = 28.0°, θmin = 2.3°
h = −11→11 k = −14→14 l = −16→16
Refinement Refinement on F2
Least-squares matrix: full R[F2 > 2σ(F2)] = 0.029
wR(F2) = 0.077
S = 0.97 4820 reflections 186 parameters 0 restraints
Primary atom site location: structure-invariant direct methods
Secondary atom site location: difference Fourier map
Hydrogen site location: inferred from neighbouring sites
H-atom parameters constrained w = 1/[σ2(F
o2) + (0.0472P)2]
where P = (Fo2 + 2Fc2)/3
(Δ/σ)max = 0.001
Δρmax = 0.91 e Å−3
Δρmin = −1.80 e Å−3
Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
supporting information
sup-2 Acta Cryst. (2005). E61, m868–m870
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 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)
x y z Uiso*/Ueq
Sn1 0.34747 (2) 0.63752 (2) 0.154153 (17) 0.00856 (8) Sn2 0.13770 (2) 0.36405 (2) 0.334696 (17) 0.00832 (8) S1 0.58686 (9) 0.70422 (8) 0.17769 (7) 0.01206 (16) S2 0.25563 (9) 0.77505 (8) 0.00775 (7) 0.01272 (16) S3 0.34584 (9) 0.41326 (8) 0.14064 (6) 0.01217 (16) S4 0.12997 (9) 0.58798 (8) 0.34600 (7) 0.01226 (16) S5 0.24852 (9) 0.22744 (8) 0.47117 (7) 0.01222 (16) S6 −0.10768 (9) 0.28440 (8) 0.32975 (7) 0.01187 (16) N1 0.4617 (3) 0.1191 (3) 0.2382 (3) 0.0172 (6)
H1N1 0.3919 0.0876 0.2080 0.026*
H2N1 0.5356 0.1758 0.1785 0.026*
H3N1 0.4075 0.1603 0.2928 0.026*
C1 0.5430 (4) 0.0112 (4) 0.2955 (3) 0.0185 (7)
H1A 0.6289 0.0465 0.3186 0.022*
H1B 0.5931 −0.0387 0.2380 0.022*
C2 0.4283 (4) −0.0776 (4) 0.4039 (3) 0.0183 (7)
H2A 0.4870 −0.1481 0.4405 0.022*
H2B 0.3813 −0.0287 0.4628 0.022*
N2 0.3002 (3) −0.1333 (3) 0.3732 (3) 0.0196 (6)
H1N2 0.2409 −0.1942 0.4383 0.029*
H2N2 0.3452 −0.1736 0.3156 0.029*
N3 0.0231 (4) −0.0186 (3) 0.3250 (3) 0.0209 (7)
H1N3 0.1225 −0.0389 0.3300 0.031*
H2N3 −0.0515 −0.0737 0.3856 0.031*
H3N3 0.0069 0.0641 0.3298 0.031*
C3 0.0089 (4) −0.0303 (4) 0.2093 (4) 0.0257 (9)
H3A −0.1039 −0.0229 0.2096 0.031*
H3B 0.0411 −0.1165 0.1993 0.031*
C4 0.1134 (5) 0.0740 (5) 0.1061 (3) 0.0277 (9)
H4A 0.0949 0.0683 0.0314 0.033*
H4B 0.0837 0.1602 0.1174 0.033*
N4 0.2832 (4) 0.0595 (3) 0.0970 (3) 0.0220 (7)
H1N4 0.3453 0.1211 0.0340 0.033*
H2N4 0.3099 −0.0195 0.0857 0.033*
supporting information
sup-3 Acta Cryst. (2005). E61, m868–m870
H1N5 0.7591 0.4119 1.0636 0.020*
H2N5 0.7114 0.5131 1.1279 0.020*
H3N5 0.8118 0.4089 1.1693 0.020*
C5 0.9384 (4) 0.5432 (3) 1.0258 (3) 0.0148 (7)
H5A 0.9813 0.5888 1.0723 0.018*
H5B 0.9128 0.6088 0.9610 0.018*
N6 0.2903 (3) 0.4523 (3) 0.6009 (2) 0.0140 (6)
H1N6 0.2649 0.3974 0.5626 0.021*
H2N6 0.2055 0.5000 0.6230 0.021*
H3N6 0.3151 0.4059 0.6666 0.021*
C6 0.4303 (4) 0.5403 (3) 0.5202 (3) 0.0146 (7)
H6A 0.4607 0.5986 0.5622 0.018*
H6B 0.4024 0.5941 0.4504 0.018*
Atomic displacement parameters (Å2)
U11 U22 U33 U12 U13 U23
Sn1 0.00919 (11) 0.00736 (13) 0.00709 (11) 0.00105 (8) −0.00028 (8) −0.00094 (8) Sn2 0.00882 (11) 0.00705 (13) 0.00717 (11) 0.00145 (8) −0.00073 (8) −0.00059 (8) S1 0.0114 (3) 0.0132 (4) 0.0111 (3) 0.0007 (3) −0.0031 (3) −0.0027 (3) S2 0.0154 (3) 0.0103 (4) 0.0109 (3) 0.0033 (3) −0.0034 (3) −0.0009 (3) S3 0.0157 (3) 0.0084 (4) 0.0084 (3) 0.0032 (3) 0.0022 (3) −0.0023 (3) S4 0.0129 (3) 0.0090 (4) 0.0113 (3) 0.0014 (3) 0.0026 (3) −0.0037 (3) S5 0.0131 (3) 0.0111 (4) 0.0111 (3) 0.0034 (3) −0.0037 (3) −0.0006 (3) S6 0.0110 (3) 0.0122 (4) 0.0119 (3) 0.0011 (3) −0.0034 (3) −0.0023 (3) N1 0.0174 (13) 0.0142 (16) 0.0152 (13) 0.0001 (12) 0.0006 (11) −0.0020 (11) C1 0.0149 (14) 0.0149 (18) 0.0227 (16) 0.0011 (13) −0.0016 (13) −0.0048 (14) C2 0.0248 (16) 0.0134 (18) 0.0191 (16) 0.0030 (14) −0.0121 (14) −0.0025 (13) N2 0.0201 (13) 0.0183 (17) 0.0160 (13) −0.0050 (12) −0.0016 (11) −0.0011 (11) N3 0.0186 (13) 0.0189 (17) 0.0201 (14) 0.0010 (12) 0.0005 (12) −0.0033 (12) C3 0.0174 (15) 0.033 (2) 0.0276 (19) 0.0012 (16) −0.0036 (15) −0.0136 (17) C4 0.0314 (19) 0.032 (2) 0.0181 (16) 0.0119 (18) −0.0081 (16) −0.0031 (16) N4 0.0256 (14) 0.0187 (17) 0.0160 (13) −0.0057 (13) −0.0009 (12) −0.0005 (12) N5 0.0144 (12) 0.0154 (15) 0.0104 (11) 0.0033 (11) −0.0028 (10) −0.0037 (10) C5 0.0136 (14) 0.0108 (17) 0.0186 (15) 0.0036 (13) −0.0032 (13) −0.0037 (13) N6 0.0120 (11) 0.0198 (16) 0.0086 (11) 0.0032 (11) −0.0003 (10) −0.0046 (11) C6 0.0121 (13) 0.0138 (18) 0.0159 (15) 0.0050 (13) −0.0017 (12) −0.0037 (13)
Geometric parameters (Å, º)
Sn1—S2 2.3337 (9) N3—H3N3 0.9100
Sn1—S1 2.3474 (8) C3—C4 1.517 (6)
Sn1—S3 2.4549 (9) C3—H3A 0.9900
Sn1—S4 2.4868 (8) C3—H3B 0.9900
Sn2—S5 2.3434 (9) C4—N4 1.468 (5)
Sn2—S6 2.3509 (8) C4—H4A 0.9900
Sn2—S4 2.4409 (9) C4—H4B 0.9900
supporting information
sup-4 Acta Cryst. (2005). E61, m868–m870
N1—C1 1.475 (5) N4—H2N4 0.9100
N1—H1N1 0.9100 N5—C5 1.497 (4)
N1—H2N1 0.9100 N5—H1N5 0.9100
N1—H3N1 0.9100 N5—H2N5 0.9100
C1—C2 1.507 (5) N5—H3N5 0.9100
C1—H1A 0.9900 C5—C5i 1.514 (7)
C1—H1B 0.9900 C5—H5A 0.9900
C2—N2 1.465 (4) C5—H5B 0.9900
C2—H2A 0.9900 N6—C6 1.489 (4)
C2—H2B 0.9900 N6—H1N6 0.9100
N2—H1N2 0.9100 N6—H2N6 0.9100
N2—H2N2 0.9100 N6—H3N6 0.9100
N3—C3 1.491 (5) C6—C6ii 1.521 (6)
N3—H1N3 0.9100 C6—H6A 0.9900
N3—H2N3 0.9100 C6—H6B 0.9900
S2—Sn1—S1 117.06 (3) H2N3—N3—H3N3 109.5 S2—Sn1—S3 111.51 (3) N3—C3—C4 111.2 (3)
S1—Sn1—S3 112.48 (3) N3—C3—H3A 109.4
S2—Sn1—S4 109.00 (3) C4—C3—H3A 109.4
S1—Sn1—S4 110.79 (3) N3—C3—H3B 109.4
S3—Sn1—S4 93.46 (3) C4—C3—H3B 109.4
S5—Sn2—S6 114.80 (3) H3A—C3—H3B 108.0 S5—Sn2—S4 113.84 (3) N4—C4—C3 110.9 (3)
S6—Sn2—S4 112.12 (3) N4—C4—H4A 109.5
S5—Sn2—S3 106.50 (3) C3—C4—H4A 109.5
S6—Sn2—S3 113.35 (3) N4—C4—H4B 109.5
S4—Sn2—S3 94.34 (3) C3—C4—H4B 109.5
Sn1—S3—Sn2 86.14 (3) H4A—C4—H4B 108.0 Sn2—S4—Sn1 85.98 (3) C4—N4—H1N4 110.5
C1—N1—H1N1 109.5 C4—N4—H2N4 108.9
C1—N1—H2N1 109.5 H1N4—N4—H2N4 108.3
H1N1—N1—H2N1 109.5 C5—N5—H1N5 109.5
C1—N1—H3N1 109.5 C5—N5—H2N5 109.5
H1N1—N1—H3N1 109.5 H1N5—N5—H2N5 109.5
H2N1—N1—H3N1 109.5 C5—N5—H3N5 109.5
N1—C1—C2 111.6 (3) H1N5—N5—H3N5 109.5
N1—C1—H1A 109.3 H2N5—N5—H3N5 109.5
C2—C1—H1A 109.3 N5—C5—C5i 108.8 (3)
N1—C1—H1B 109.3 N5—C5—H5A 109.9
C2—C1—H1B 109.3 C5i—C5—H5A 109.9
H1A—C1—H1B 108.0 N5—C5—H5B 109.9
N2—C2—C1 111.0 (3) C5i—C5—H5B 109.9
N2—C2—H2A 109.4 H5A—C5—H5B 108.3
C1—C2—H2A 109.4 C6—N6—H1N6 109.5
N2—C2—H2B 109.4 C6—N6—H2N6 109.5
C1—C2—H2B 109.4 H1N6—N6—H2N6 109.5
supporting information
sup-5 Acta Cryst. (2005). E61, m868–m870
C2—N2—H1N2 108.8 H1N6—N6—H3N6 109.5
C2—N2—H2N2 108.6 H2N6—N6—H3N6 109.5
H1N2—N2—H2N2 107.9 N6—C6—C6ii 109.1 (4)
C3—N3—H1N3 109.5 N6—C6—H6A 109.9
C3—N3—H2N3 109.5 C6ii—C6—H6A 109.9
H1N3—N3—H2N3 109.5 N6—C6—H6B 109.9
C3—N3—H3N3 109.5 C6ii—C6—H6B 109.9
H1N3—N3—H3N3 109.5 H6A—C6—H6B 108.3
Symmetry codes: (i) −x+2, −y+1, −z+2; (ii) −x+1, −y+1, −z+1.
Hydrogen-bond geometry (Å, º)
D—H···A D—H H···A D···A D—H···A
N1—H1N1···N4 0.91 1.95 2.833 (4) 162 N1—H2N1···S2iii 0.91 2.40 3.228 (3) 151
N1—H3N1···S5 0.91 2.49 3.390 (3) 168 N2—H1N2···S6iv 0.91 2.65 3.477 (3) 152
N2—H2N2···S1v 0.91 2.83 3.683 (3) 157
N3—H1N3···N2 0.91 1.97 2.849 (5) 162 N3—H2N3···S5iv 0.91 2.36 3.271 (3) 174
N3—H3N3···S6 0.91 2.55 3.436 (4) 164 N4—H1N4···S1iii 0.91 2.68 3.523 (3) 155
N4—H2N4···S2v 0.91 2.72 3.533 (3) 150
N5—H1N5···S2ii 0.91 2.41 3.263 (3) 157
N5—H2N5···S1vi 0.91 2.44 3.303 (3) 159
N5—H3N5···S6vii 0.91 2.35 3.260 (3) 174
N6—H1N6···S5 0.91 2.40 3.293 (3) 167 N6—H2N6···S6viii 0.91 2.60 3.399 (3) 147
N6—H3N6···S1ii 0.91 2.35 3.250 (3) 173