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Two new dialkyl­ammonium thio­sulfates, namely bis­(di­isopropyl­ammonium) thio­sulfate, 2C6H16N+·S2O32−, (I), and bis­(tert-butyl­ammonium) thio­sulfate, 2C4H12N+·S2O32−, (II), have been characterized. The secondary ammonium salt (I) crystallizes with Z = 4, while the primary ammonium salt (II), with more hydrogen-bond donors, crystallizes with Z = 8 and a noncrystallographic centre of inversion. In both salts, the organic cations and thio­sulfate anions are linked within extensive N—H...O and N—H...S hydrogen-bond networks, forming extended two-dimensional layers. Layers are parallel to (10\overline{1}) in (I) and to (002) in (II), and have a polar inter­ior and a nonpolar hydro­carbon exterior. The layered structure and hydrogen-bond motifs observed in (I) and (II) are similar to those in related ammonium sulfates.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270113001327/dt3017sup1.cif
Contains datablocks global, I, II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270113001327/dt3017Isup2.hkl
Contains datablock I

smi

Smiles format file https://doi.org/10.1107/S0108270113001327/dt3017Isup4.smi
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S0108270113001327/dt3017Isup6.cml
Supplementary material

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270113001327/dt3017IIsup3.hkl
Contains datablock II

smi

Smiles format file https://doi.org/10.1107/S0108270113001327/dt3017IIsup5.smi
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S0108270113001327/dt3017IIsup7.cml
Supplementary material

CCDC references: 925779; 925780

Comment top

A few years ago, we began an examination of N—H···S hydrogen bonds in great detail and have prepared and structurally characterized several alkylammonium thiolate adducts (Baranowska et al., 2003, 2006). We found that the hydrogen bonds in these adducts were of a robust charge-assisted N+–H···S- type and because of the proton transfer they are better described as salts (Becker et al., 2004). We turned our attention to the thiosulfate anion because it can act as an S-donor ligand (Pladzyk et al., 2012) and besides oxygen, one of its S atoms is able to serve as a hydrogen-bond acceptor.

Thiosulfates belong to the basic type of inorganic anion. In most applications, salts with alkali metal cations or NH4+ are used as solids or in aqueous solutions. By replacement of the cation with an organic species, RnNH4-n+ (n = 1–4), we expect to obtain new substances with enhanced solubility and increased reactivity in non-aqueous phases. Their chemical and physical properties, as well as their crystal structures, were rarely examined. Although a recent search of the Cambridge Structural Database (CSD, Version 5.33, August 2012; Allen, 2002) gives over 100 records containing the S2O32- anion, there are only six alkylammonium thiosulfates, mainly obtained by chance during studies focussed on other targets. Two of these papers deal with protonated cryptands (Maubert et al., 2001; Nelson et al., 2004) and the next compounds are tetraalkylammonium derivatives (Leyten et al., 1988; Yang & Ng, 2011). The most relevant reports are papers containing structural details of thiosulfate derivatives of piperazine (Srinivasan et al., 2011) and amantadine (Jiang et al., 1998).

In this study, we investigated two new members of this interesting class of compounds, namely bis(diisopropylammonium) thiosulfate, (iPr2NH2)2S2O3, (I) (Fig. 1), and bis(tert-butylammonium) thiosulfate, (t-BuNH3)2S2O3, (II) (Fig. 2).

The asymmetric unit of (I) contains two iPr2NH2+ cations and one S2O32- anion (Fig. 1) connected through four types of charge-assisted hydrogen bonds. Two of these hydrogen bonds, viz. N1—H1M···O1i and N1—H1N···O3 (see Table 1 for details of the hydrogen bonds and symmetry codes), form a strong <it>R</it>44(12) motif (denoted A) about the inversion centre (Etter, 1990). Larger centrosymmetric <it>R</it>1212(36) rings (denoted B) incorporating six positive and six negative ions are also formed by using both N1—H and N2—H donors (Fig. 3).

It is noteworthy that four t-BuNH3+ cations and two S2O32- anions form the asymmetric unit of (II) (Fig. 2). A noncrystallographic centre of inversion lies about (1/2, 0.39, 1/4). The ions in (II) are connected by 12 types of charge-assisted hydrogen bonds, forming quite a complicated network. Hydrogen bonds form a strong <it>R</it>42(8) structural motif (denoted C) and several larger rings, viz. <it>R</it>43(10) (denoted D and D'; based on OO+O acceptors), <it>R</it>44(12) (denoted E, F and F'; E is based on OS+OS and both F and F' on OO+OS acceptor atoms). Motifs C and E have the noncrystallographic centres of inversion in their middles. Motifs D' and F' are related to D and F also by such an inversion. [For more details on hydrogen bonds and symmetry codes in (II), see Table 2.]

Although there are some differences in their hydrogen bonding, both compounds crystallize in the space group P21/n and exhibit a similar layered type of structure. Each layer has a hydrophilic interior (where heteroatoms and hydrogen bonds are located) and a hydrophobic exterior (tert-butyl or isopropyl groups). These layers are parallel to the (101) plane in (I) and to the (002) plane in (II). Van der Waals interactions of external alkyl groups combine these layers into three-dimensional structures (Fig. 5).

Similar to (II), layers parallel to (002) and <it>R</it>43(10) (based on OO+O or OS+O acceptors) and <it>R</it>44(12) (OO+OS acceptors) motifs, can be found in the structure of amantadinum thiosulfate (Jiang et al., 1998). Hovever, the smallest motif analogueous to C = <it>R</it>42(8) is absent here.

It is worthwhile comparing the structures of (I) and (II) to the related sulfates. The structure of bis(diisopropylammonium) sulfate (Reiß & Engel, 2004) also has a layered structure parallel to (101) and is bound inside layers with <it>R</it>44(12) motifs and large <it>R</it>1212(36) motifs, both of which are centrosymmetric. The structure of tris(diisopropylammonium) bisulfate sulfate, (iPr2NH2)3H(SO4)2 (Mohammadnezhad et al., 2008), is of the three-dimensional type.

Bis(tert-butylammonium) sulfate (Guerfel et al., 2000), although it crystallizes in the C2/c space group, also exhibits a layered structure parallel to (002) and has <it>R</it>44(12) and <it>R</it>43(10) motifs within the layer, obviously based on O-atom acceptors. In this case, the asymmetric unit contains a protonated amine and half of the anion.

It is noteworthy that the structures of (I) and (II) do not contain water. This is a good indicator for good solubility in organic phases. This should also enhance the hydrolytic stability of the substances during storage. In two protonated azacryptate hosts, which encapsulate thiosulfate anion guests, water serves as an additional hydrogen-bond donor and the perchlorate anion as a hydrogen-bond acceptor (Maubert et al., 2001; Nelson et al., 2004). Water is also an integral component of the hydrogen-bond network in piperazinediium thiosulfate monohydrate (Srinivasan et al., 2011). Quarternary thiosulfates are hydrated also. Bis(tetraethylammonium) thiosulfate dihydrate (Leyten et al., 1988) and bis(tetramethylammonium) thiosulfate tetrahydrate (Yang & Ng, 2011), being devoid of N—H bonds, exhibit a different organization of hydrogen bonding based on O—H···O hydrogen bonds. The case of bis(amantadinium) thiosulfate (Jiang et al., 1998), with R = 9.37%, is the only one preceeding the presented data [clarify?], where an –NH3+ group is the sole hydrogen-bond donor and no water can be found in the crystal phase.

Related literature top

For related literature, see: Allen (2002); Baranowska et al. (2003, 2006); Becker et al. (2004); Etter (1990); Guerfel et al. (2000); Jiang et al. (1998); Leyten et al. (1988); Maubert et al. (2001); Mohammadnezhad et al. (2008); Nelson et al. (2004); Piękoś & Wojnowski (1962); Pladzyk et al. (2012); Reiß & Engel (2004); Srinivasan et al. (2011); Yang & Ng (2011).

Experimental top

Alkylammonium thiosulfates can be obtained by different methods. Often an amine is heated with a sulfur or sulfur-containing compound. Elemental sulfur S8 was used in the synthesis of (I), while tri-tert-pentoxysilanethiol [(tAmO)3SiSH; Piękoś & Wojnowski, 1962] served as a source of sulfur during the preparation of (II).

For the preparation of (I), diisopropylamine (1.5 ml, 11 mmol) was mixed with elemental sulfur (0.48 g, 15 mmol) in toluene (5 ml) and the mixture was refluxed for 1.5 h. The resulting dark-brown liquid was poured into hot methanol (20 ml), filtered and the filtrate left to cool and evaporate slowly. After one week, large colourless crystals had formed. After recrystalization from a small amount of methanol, crystals suitable for single-crystal X-ray diffraction analysis were obtained.

For the preparation of (II), tert-butylamine (0.2 ml, 2 mmol) was added to a solution of (tAmO)3SiSH (0.65 g, 2 mmol) in toluene (5 ml) and the mixture was heated at ca 373 K for several hours and then left for one week at room temperature after which time small transparent crystals had precipitated. After recrystalization from hot toluene, crystals suitable for single-crystal X-ray diffraction analysis were obtained.

Refinement top

H atoms were placed at calculated positions (C–H = 0.98–0.99 Å) and were treated as riding on their parent atoms, with U(H) values set at 1.2–1.5 times Ueq(C). The N—H distances were restrained to 0.850 (10) Å.

Computing details top

For both compounds, data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell refinement: CrysAlis PRO (Oxford Diffraction, 2010); data reduction: CrysAlis PRO (Oxford Diffraction, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009) and Mercury (Macrae et al., 2008); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The structure of (I), with displacement ellipsoids drawn at the 50% probability level. Selected hydrogen bonds are marked with dotted lines.
[Figure 2] Fig. 2. The structure of (II), with displacement ellipsoids drawn at 50% probability level. Selected hydrogen bonds are marked with dotted lines.
[Figure 3] Fig. 3. The hydrogen-bond pattern and ring motifs found in (I). Isopropyl groups are reduced to their first C atom for clarity. Motifs: A = <it>R</it>44(12) and B = <it>R</it>1212(36). [Symmetry codes: (i) -x+1, -y+1, -z; (ii) x-1/2, -y+3/2, z-1/2; (iii) -x+1/2, y+1/2, -z-1/2; (iv) -x+1, -y+2, -z; (v) x, y+1, z; (vi) -x+3/2, y+1/2, -z+1/2; (vii) x+1/2, -y+3/2, z+1/2.]
[Figure 4] Fig. 4. Selected structural ring motifs involving thiosulfate anions found in (II). tert-Butly groups are reduced to their first C atom for clarity. Motifs: C = <it>R</it>42(8), D = D' = <it>R</it>43(10) and E = F = F' = <it>R</it>44(12). [Symmetry codes: (i) -x+3/2, y+1/2, -z+1/2; (ii) x+1, y, z; (iii) -x+3/2, y-1/2, -z+1/2; (iv) x, y-1, z; (v) -x+1/2, y-1/2, -z+1/2; (vi) x-1, y, z.]
[Figure 5] Fig. 5. Packing diagrams viewed along the [010] direction. Layers present in (a) (I) and (b) (II) are parallel to (101) and (002), respectively. Selected hydrogen bonds are marked with dotted lines.
(I) Bis(diisopropylammonium) thiosulfate top
Crystal data top
2C6H16N+·S2O32F(000) = 696
Mr = 316.52Dx = 1.173 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 13303 reflections
a = 8.6437 (3) Åθ = 2.3–28.8°
b = 9.5322 (3) ŵ = 0.30 mm1
c = 21.8594 (8) ÅT = 120 K
β = 95.657 (3)°Prism, colourless
V = 1792.30 (11) Å30.42 × 0.38 × 0.31 mm
Z = 4
Data collection top
Oxford Diffraction Xcalibur (Sapphire2, large Be window)
diffractometer
3162 independent reflections
Graphite monochromator2858 reflections with I > 2σ(I)
Detector resolution: 8.1883 pixels mm-1Rint = 0.027
ω scansθmax = 25.0°, θmin = 2.3°
Absorption correction: analytical
[CrysAlis PRO (Oxford Diffraction, 2010), based on expressions derived by Clark & Reid (1995)]
h = 1010
Tmin = 0.909, Tmax = 0.928k = 1111
18736 measured reflectionsl = 2525
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)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.110H atoms treated by a mixture of independent and constrained refinement
S = 1.09 w = 1/[σ2(Fo2) + (0.0565P)2 + 1.5638P]
where P = (Fo2 + 2Fc2)/3
3162 reflections(Δ/σ)max < 0.001
196 parametersΔρmax = 0.60 e Å3
4 restraintsΔρmin = 0.26 e Å3
Crystal data top
2C6H16N+·S2O32V = 1792.30 (11) Å3
Mr = 316.52Z = 4
Monoclinic, P21/nMo Kα radiation
a = 8.6437 (3) ŵ = 0.30 mm1
b = 9.5322 (3) ÅT = 120 K
c = 21.8594 (8) Å0.42 × 0.38 × 0.31 mm
β = 95.657 (3)°
Data collection top
Oxford Diffraction Xcalibur (Sapphire2, large Be window)
diffractometer
3162 independent reflections
Absorption correction: analytical
[CrysAlis PRO (Oxford Diffraction, 2010), based on expressions derived by Clark & Reid (1995)]
2858 reflections with I > 2σ(I)
Tmin = 0.909, Tmax = 0.928Rint = 0.027
18736 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0424 restraints
wR(F2) = 0.110H atoms treated by a mixture of independent and constrained refinement
S = 1.09Δρmax = 0.60 e Å3
3162 reflectionsΔρmin = 0.26 e Å3
196 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
H2N0.720 (3)0.2172 (13)0.2016 (10)0.022 (6)*
H1N0.3868 (16)0.549 (2)0.0570 (10)0.024 (6)*
H2M0.702 (3)0.126 (3)0.2500 (5)0.027 (6)*
H1M0.284 (3)0.580 (3)0.0068 (5)0.028 (6)*
N10.2993 (2)0.58701 (19)0.04535 (8)0.0201 (4)
C10.3108 (2)0.7406 (2)0.06148 (10)0.0253 (5)
H10.34250.74920.10660.03*
C20.4372 (3)0.8038 (3)0.02708 (11)0.0320 (5)
H2A0.53620.75720.03970.048*
H2B0.44640.90420.03650.048*
H2C0.41080.79110.01720.048*
C30.1558 (3)0.8140 (3)0.04718 (11)0.0328 (5)
H3A0.16780.91420.05650.049*
H3B0.07930.77330.07230.049*
H3C0.120.80180.00350.049*
C40.1767 (2)0.5011 (2)0.07229 (10)0.0231 (5)
H40.0720.53530.05510.028*
C50.1959 (3)0.3502 (2)0.05232 (11)0.0293 (5)
H5A0.2980.31530.06920.044*
H5B0.18810.34550.00730.044*
H5C0.11420.29230.06750.044*
C60.1896 (3)0.5158 (3)0.14167 (10)0.0283 (5)
H6A0.29480.49030.15880.042*
H6B0.11410.45360.15850.042*
H6C0.16810.61320.15250.042*
N20.69938 (19)0.13311 (18)0.21137 (8)0.0187 (4)
C70.8243 (2)0.0405 (2)0.19015 (9)0.0219 (4)
H70.80450.05870.20210.026*
C80.8241 (3)0.0488 (2)0.12061 (10)0.0299 (5)
H8A0.72860.00630.1010.045*
H8B0.91440.00170.1080.045*
H8C0.82920.14730.10810.045*
C90.9778 (3)0.0894 (2)0.22363 (11)0.0297 (5)
H9A1.06160.02680.21360.045*
H9B0.97050.08780.26810.045*
H9C10.18520.21080.045*
C100.5346 (2)0.1093 (2)0.18428 (9)0.0227 (4)
H100.52870.12650.1390.027*
C110.4830 (3)0.0403 (2)0.19489 (11)0.0290 (5)
H11A0.54690.10530.17340.043*
H11B0.37360.05120.17910.043*
H11C0.49520.06080.2390.043*
C120.4342 (3)0.2171 (2)0.21261 (11)0.0291 (5)
H12A0.44070.20290.25720.044*
H12B0.3260.20650.19510.044*
H12C0.47090.31160.20380.044*
S10.78107 (7)0.67817 (6)0.13521 (2)0.02641 (17)
S20.72833 (5)0.47611 (5)0.12360 (2)0.01745 (15)
O10.81990 (17)0.41513 (16)0.07674 (6)0.0250 (3)
O20.76781 (18)0.40428 (15)0.18289 (6)0.0249 (3)
O30.56176 (17)0.45898 (17)0.10376 (7)0.0296 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0169 (9)0.0279 (10)0.0153 (9)0.0010 (7)0.0012 (7)0.0014 (7)
C10.0279 (11)0.0270 (11)0.0206 (10)0.0001 (9)0.0006 (8)0.0033 (9)
C20.0264 (12)0.0342 (13)0.0343 (13)0.0048 (10)0.0016 (10)0.0051 (10)
C30.0321 (13)0.0313 (13)0.0359 (13)0.0059 (10)0.0073 (10)0.0000 (10)
C40.0166 (10)0.0317 (12)0.0213 (11)0.0010 (9)0.0029 (8)0.0025 (9)
C50.0269 (11)0.0318 (12)0.0291 (12)0.0049 (10)0.0025 (9)0.0009 (10)
C60.0263 (11)0.0376 (13)0.0215 (11)0.0024 (10)0.0053 (9)0.0026 (9)
N20.0212 (9)0.0194 (9)0.0155 (9)0.0006 (7)0.0024 (7)0.0016 (7)
C70.0250 (11)0.0193 (10)0.0223 (11)0.0033 (8)0.0058 (8)0.0025 (8)
C80.0389 (13)0.0276 (12)0.0252 (12)0.0062 (10)0.0127 (10)0.0012 (9)
C90.0229 (11)0.0302 (12)0.0362 (13)0.0018 (9)0.0047 (9)0.0045 (10)
C100.0210 (10)0.0280 (11)0.0184 (10)0.0003 (9)0.0011 (8)0.0025 (8)
C110.0237 (11)0.0291 (12)0.0336 (13)0.0043 (9)0.0004 (9)0.0029 (10)
C120.0239 (11)0.0284 (12)0.0359 (13)0.0029 (9)0.0072 (9)0.0058 (10)
S10.0346 (3)0.0204 (3)0.0242 (3)0.0009 (2)0.0028 (2)0.0015 (2)
S20.0162 (3)0.0206 (3)0.0155 (3)0.00044 (19)0.00114 (18)0.00144 (18)
O10.0258 (8)0.0300 (8)0.0200 (7)0.0005 (6)0.0060 (6)0.0045 (6)
O20.0346 (8)0.0219 (8)0.0177 (7)0.0020 (6)0.0007 (6)0.0030 (6)
O30.0166 (7)0.0340 (9)0.0374 (9)0.0010 (6)0.0015 (6)0.0017 (7)
Geometric parameters (Å, º) top
N1—C41.504 (3)N2—H2N0.853 (10)
N1—C11.507 (3)N2—H2M0.846 (10)
N1—H1N0.853 (10)C7—C81.522 (3)
N1—H1M0.844 (10)C7—C91.523 (3)
C1—C21.511 (3)C7—H71
C1—C31.517 (3)C8—H8A0.98
C1—H11C8—H8B0.98
C2—H2A0.98C8—H8C0.98
C2—H2B0.98C9—H9A0.98
C2—H2C0.98C9—H9B0.98
C3—H3A0.98C9—H9C0.98
C3—H3B0.98C10—C121.516 (3)
C3—H3C0.98C10—C111.518 (3)
C4—C61.516 (3)C10—H101
C4—C51.517 (3)C11—H11A0.98
C4—H41C11—H11B0.98
C5—H5A0.98C11—H11C0.98
C5—H5B0.98C12—H12A0.98
C5—H5C0.98C12—H12B0.98
C6—H6A0.98C12—H12C0.98
C6—H6B0.98S1—S21.9898 (7)
C6—H6C0.98S2—O31.4713 (15)
N2—C71.504 (3)S2—O11.4743 (15)
N2—C101.505 (3)S2—O21.4756 (15)
C4—N1—C1118.03 (16)C7—N2—H2M108.0 (17)
C4—N1—H1N107.0 (16)C10—N2—H2M108.3 (16)
C1—N1—H1N107.6 (16)H2N—N2—H2M110 (2)
C4—N1—H1M107.2 (17)N2—C7—C8110.31 (17)
C1—N1—H1M108.4 (17)N2—C7—C9106.84 (17)
H1N—N1—H1M108 (2)C8—C7—C9112.29 (18)
N1—C1—C2107.78 (17)N2—C7—H7109.1
N1—C1—C3111.30 (18)C8—C7—H7109.1
C2—C1—C3112.37 (19)C9—C7—H7109.1
N1—C1—H1108.4C7—C8—H8A109.5
C2—C1—H1108.4C7—C8—H8B109.5
C3—C1—H1108.4H8A—C8—H8B109.5
C1—C2—H2A109.5C7—C8—H8C109.5
C1—C2—H2B109.5H8A—C8—H8C109.5
H2A—C2—H2B109.5H8B—C8—H8C109.5
C1—C2—H2C109.5C7—C9—H9A109.5
H2A—C2—H2C109.5C7—C9—H9B109.5
H2B—C2—H2C109.5H9A—C9—H9B109.5
C1—C3—H3A109.5C7—C9—H9C109.5
C1—C3—H3B109.5H9A—C9—H9C109.5
H3A—C3—H3B109.5H9B—C9—H9C109.5
C1—C3—H3C109.5N2—C10—C12107.13 (17)
H3A—C3—H3C109.5N2—C10—C11111.26 (17)
H3B—C3—H3C109.5C12—C10—C11112.68 (18)
N1—C4—C6110.87 (17)N2—C10—H10108.6
N1—C4—C5107.58 (17)C12—C10—H10108.6
C6—C4—C5112.12 (19)C11—C10—H10108.6
N1—C4—H4108.7C10—C11—H11A109.5
C6—C4—H4108.7C10—C11—H11B109.5
C5—C4—H4108.7H11A—C11—H11B109.5
C4—C5—H5A109.5C10—C11—H11C109.5
C4—C5—H5B109.5H11A—C11—H11C109.5
H5A—C5—H5B109.5H11B—C11—H11C109.5
C4—C5—H5C109.5C10—C12—H12A109.5
H5A—C5—H5C109.5C10—C12—H12B109.5
H5B—C5—H5C109.5H12A—C12—H12B109.5
C4—C6—H6A109.5C10—C12—H12C109.5
C4—C6—H6B109.5H12A—C12—H12C109.5
H6A—C6—H6B109.5H12B—C12—H12C109.5
C4—C6—H6C109.5O3—S2—O1109.16 (9)
H6A—C6—H6C109.5O3—S2—O2110.01 (9)
H6B—C6—H6C109.5O1—S2—O2109.50 (9)
C7—N2—C10118.09 (16)O3—S2—S1110.50 (7)
C7—N2—H2N107.6 (16)O1—S2—S1109.77 (7)
C10—N2—H2N104.7 (16)O2—S2—S1107.87 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1M···O1i0.84 (1)1.95 (1)2.764 (2)161 (2)
N1—H1N···O30.85 (1)1.94 (1)2.774 (2)165 (2)
N2—H2N···O20.85 (1)1.88 (1)2.737 (2)178 (2)
N2—H2M···S1ii0.85 (1)2.55 (1)3.3688 (17)164 (2)
Symmetry codes: (i) x+1, y+1, z; (ii) x+3/2, y1/2, z+1/2.
(II) Bis(tert-butylammonium) thiosulfate top
Crystal data top
2C4H12N+·S2O32F(000) = 1136
Mr = 260.41Dx = 1.202 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 6114 reflections
a = 11.7834 (4) Åθ = 2.1–28.8°
b = 12.3519 (6) ŵ = 0.36 mm1
c = 19.9312 (8) ÅT = 120 K
β = 97.017 (4)°Prism, colourless
V = 2879.2 (2) Å30.54 × 0.12 × 0.03 mm
Z = 8
Data collection top
Oxford Diffraction Xcalibur (Sapphire2, large Be window)
diffractometer
5063 independent reflections
Graphite monochromator3704 reflections with I > 2σ(I)
Detector resolution: 8.1883 pixels mm-1Rint = 0.023
ω scansθmax = 25°, θmin = 2.4°
Absorption correction: analytical
[CrysAlis PRO (Oxford Diffraction, 2010), based on expressions derived by Clark & Reid (1995)]
h = 1314
Tmin = 0.834, Tmax = 0.986k = 1414
10821 measured reflectionsl = 1523
Refinement top
Refinement on F212 restraints
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.034 w = 1/[σ2(Fo2) + (0.0507P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.084(Δ/σ)max = 0.001
S = 0.96Δρmax = 0.47 e Å3
5063 reflectionsΔρmin = 0.21 e Å3
331 parameters
Crystal data top
2C4H12N+·S2O32V = 2879.2 (2) Å3
Mr = 260.41Z = 8
Monoclinic, P21/nMo Kα radiation
a = 11.7834 (4) ŵ = 0.36 mm1
b = 12.3519 (6) ÅT = 120 K
c = 19.9312 (8) Å0.54 × 0.12 × 0.03 mm
β = 97.017 (4)°
Data collection top
Oxford Diffraction Xcalibur (Sapphire2, large Be window)
diffractometer
5063 independent reflections
Absorption correction: analytical
[CrysAlis PRO (Oxford Diffraction, 2010), based on expressions derived by Clark & Reid (1995)]
3704 reflections with I > 2σ(I)
Tmin = 0.834, Tmax = 0.986Rint = 0.023
10821 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.03412 restraints
wR(F2) = 0.084H atoms treated by a mixture of independent and constrained refinement
S = 0.96Δρmax = 0.47 e Å3
5063 reflectionsΔρmin = 0.21 e Å3
331 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
N10.60140 (14)0.26074 (14)0.31094 (8)0.0174 (4)
C10.58808 (15)0.22664 (16)0.38228 (9)0.0192 (4)
C20.53094 (17)0.32054 (17)0.41466 (9)0.0274 (5)
H2A0.57720.38610.41250.033*
H2B0.52420.30320.4620.033*
H2C0.45460.33270.39030.033*
C30.51377 (16)0.12543 (17)0.37739 (10)0.0242 (5)
H3A0.43850.14250.35320.029*
H3B0.50480.09970.4230.029*
H3C0.55020.06890.35290.029*
C40.70735 (16)0.20306 (18)0.41860 (9)0.0280 (5)
H4A0.74160.1430.3960.034*
H4B0.70160.18340.46570.034*
H4C0.75530.26770.41740.034*
H1M0.6384 (15)0.2156 (14)0.2900 (9)0.028 (6)*
H1N0.5361 (10)0.2658 (17)0.2875 (8)0.028 (6)*
H1O0.6340 (15)0.3214 (10)0.3088 (9)0.021 (6)*
N20.40549 (14)0.52191 (14)0.19686 (8)0.0180 (4)
C50.42213 (16)0.54972 (17)0.12514 (9)0.0218 (4)
C60.49084 (19)0.45693 (19)0.09964 (10)0.0327 (5)
H6A0.56380.44990.12870.039*
H6B0.50530.47190.05320.039*
H6C0.44750.38940.10070.039*
C70.48764 (17)0.65643 (18)0.12711 (11)0.0325 (5)
H7A0.44330.7130.14660.039*
H7B0.50010.6770.08110.039*
H7C0.56160.64790.15490.039*
C80.30479 (17)0.5606 (2)0.08455 (10)0.0329 (5)
H8A0.2610.4940.08890.039*
H8B0.31350.57280.03690.039*
H8C0.26420.62190.10180.039*
H2M0.3764 (15)0.4580 (10)0.1990 (9)0.020 (5)*
H2N0.3618 (15)0.5653 (14)0.2144 (9)0.032 (6)*
H2O0.4698 (11)0.5195 (18)0.2216 (9)0.033 (6)*
N30.62268 (14)0.77725 (15)0.32429 (8)0.0171 (4)
C90.65158 (15)0.75167 (15)0.39848 (8)0.0170 (4)
C100.59792 (17)0.64271 (16)0.41156 (9)0.0248 (5)
H10A0.51480.64730.40020.03*
H10B0.61620.62360.45940.03*
H10C0.62830.58710.38350.03*
C110.60398 (16)0.84248 (16)0.43859 (9)0.0228 (4)
H11A0.64150.91080.42950.027*
H11B0.61830.8260.4870.027*
H11C0.52150.8490.42510.027*
C120.78131 (15)0.74653 (17)0.41278 (9)0.0249 (5)
H12A0.80980.68760.38650.03*
H12B0.80360.73330.46110.03*
H12C0.8140.81530.40.03*
H3M0.6522 (15)0.7323 (13)0.2991 (8)0.022 (6)*
H3N0.6554 (15)0.8364 (11)0.3162 (9)0.025 (6)*
H3O0.5505 (8)0.7800 (17)0.3116 (9)0.021 (5)*
N40.37223 (14)0.00434 (15)0.17111 (8)0.0177 (4)
C130.34307 (15)0.03858 (16)0.09815 (9)0.0186 (4)
C140.40860 (17)0.14174 (17)0.08805 (10)0.0274 (5)
H14A0.38570.19820.11820.033*
H14B0.39170.16570.0410.033*
H14C0.49080.12810.09840.033*
C150.37825 (17)0.05355 (17)0.05410 (9)0.0253 (5)
H15A0.46010.06810.06540.03*
H15B0.36270.0330.00640.03*
H15C0.33460.11880.06220.03*
C160.21438 (16)0.05722 (18)0.08617 (10)0.0281 (5)
H16A0.17460.0090.09710.034*
H16B0.19190.07620.03870.034*
H16C0.19380.11650.11510.034*
H4M0.3407 (14)0.0555 (10)0.1801 (9)0.016 (5)*
H4N0.3513 (17)0.0494 (14)0.1991 (8)0.029 (6)*
H4O0.4438 (9)0.0048 (17)0.1819 (9)0.023 (6)*
S10.15473 (4)0.34224 (4)0.18497 (2)0.02517 (14)
S20.26742 (4)0.27043 (4)0.25350 (2)0.01713 (12)
O10.24868 (11)0.30692 (11)0.32133 (6)0.0238 (3)
O20.25535 (10)0.15144 (11)0.24898 (6)0.0220 (3)
O30.38325 (10)0.30081 (11)0.23862 (6)0.0230 (3)
S30.84944 (4)0.43865 (5)0.32669 (2)0.02598 (14)
S40.74355 (4)0.51268 (4)0.25539 (2)0.01690 (12)
O40.75859 (11)0.63157 (11)0.25980 (6)0.0233 (3)
O50.62567 (10)0.48561 (11)0.26739 (6)0.0221 (3)
O60.76708 (11)0.47533 (11)0.18864 (6)0.0234 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0177 (9)0.0115 (10)0.0241 (9)0.0021 (8)0.0066 (7)0.0006 (7)
C10.0198 (9)0.0184 (11)0.0204 (9)0.0002 (9)0.0059 (8)0.0014 (8)
C20.0336 (11)0.0226 (12)0.0276 (10)0.0010 (10)0.0100 (9)0.0027 (9)
C30.0250 (10)0.0184 (12)0.0307 (11)0.0009 (9)0.0088 (8)0.0054 (9)
C40.0237 (10)0.0328 (13)0.0276 (10)0.0002 (10)0.0035 (8)0.0018 (10)
N20.0176 (9)0.0130 (10)0.0241 (9)0.0002 (8)0.0053 (7)0.0021 (7)
C50.0225 (10)0.0211 (12)0.0228 (10)0.0043 (9)0.0071 (8)0.0075 (8)
C60.0417 (13)0.0314 (14)0.0264 (11)0.0111 (11)0.0104 (10)0.0012 (10)
C70.0284 (11)0.0276 (14)0.0435 (12)0.0045 (10)0.0124 (10)0.0161 (11)
C80.0291 (11)0.0425 (15)0.0271 (11)0.0059 (11)0.0039 (9)0.0069 (10)
N30.0170 (9)0.0151 (10)0.0199 (8)0.0002 (8)0.0050 (7)0.0005 (7)
C90.0206 (10)0.0143 (10)0.0166 (9)0.0019 (8)0.0043 (7)0.0016 (8)
C100.0309 (11)0.0184 (11)0.0263 (10)0.0040 (10)0.0082 (9)0.0026 (9)
C110.0250 (10)0.0226 (12)0.0208 (9)0.0020 (9)0.0029 (8)0.0040 (9)
C120.0209 (10)0.0254 (12)0.0281 (10)0.0010 (9)0.0017 (8)0.0051 (9)
N40.0181 (9)0.0143 (10)0.0214 (9)0.0014 (8)0.0054 (7)0.0004 (8)
C130.0207 (10)0.0168 (11)0.0182 (9)0.0019 (8)0.0018 (8)0.0006 (8)
C140.0343 (11)0.0199 (12)0.0283 (10)0.0062 (10)0.0054 (9)0.0038 (9)
C150.0312 (11)0.0235 (12)0.0216 (10)0.0004 (10)0.0045 (8)0.0045 (9)
C160.0222 (10)0.0287 (13)0.0324 (11)0.0011 (10)0.0003 (9)0.0010 (10)
S10.0197 (3)0.0255 (3)0.0294 (3)0.0007 (2)0.0005 (2)0.0031 (2)
S20.0171 (2)0.0118 (3)0.0233 (2)0.0001 (2)0.00557 (18)0.0007 (2)
O10.0295 (7)0.0174 (8)0.0248 (7)0.0037 (6)0.0043 (6)0.0018 (6)
O20.0247 (7)0.0129 (7)0.0305 (7)0.0013 (6)0.0116 (6)0.0013 (6)
O30.0154 (6)0.0207 (8)0.0331 (7)0.0023 (6)0.0045 (6)0.0044 (6)
S30.0197 (3)0.0273 (3)0.0304 (3)0.0002 (2)0.0008 (2)0.0058 (2)
S40.0186 (2)0.0107 (3)0.0225 (2)0.0007 (2)0.00668 (18)0.00005 (19)
O40.0297 (7)0.0120 (7)0.0309 (7)0.0005 (6)0.0147 (6)0.0026 (6)
O50.0174 (7)0.0196 (8)0.0298 (7)0.0007 (6)0.0050 (6)0.0046 (6)
O60.0297 (7)0.0177 (8)0.0241 (7)0.0014 (6)0.0080 (6)0.0008 (6)
Geometric parameters (Å, º) top
N1—C11.509 (2)C9—C121.522 (2)
N1—H1M0.848 (9)C9—C101.523 (3)
N1—H1N0.853 (9)C9—C111.524 (2)
N1—H1O0.845 (9)C10—H10A0.98
C1—C31.523 (3)C10—H10B0.98
C1—C21.524 (3)C10—H10C0.98
C1—C41.528 (2)C11—H11A0.98
C2—H2A0.98C11—H11B0.98
C2—H2B0.98C11—H11C0.98
C2—H2C0.98C12—H12A0.98
C3—H3A0.98C12—H12B0.98
C3—H3B0.98C12—H12C0.98
C3—H3C0.98N4—C131.513 (2)
C4—H4A0.98N4—H4M0.856 (9)
C4—H4B0.98N4—H4N0.845 (9)
C4—H4C0.98N4—H4O0.852 (9)
N2—C51.506 (2)C13—C141.516 (3)
N2—H2M0.864 (9)C13—C161.524 (2)
N2—H2N0.848 (9)C13—C151.525 (3)
N2—H2O0.853 (9)C14—H14A0.98
C5—C81.520 (3)C14—H14B0.98
C5—C71.526 (3)C14—H14C0.98
C5—C61.526 (3)C15—H15A0.98
C6—H6A0.98C15—H15B0.98
C6—H6B0.98C15—H15C0.98
C6—H6C0.98C16—H16A0.98
C7—H7A0.98C16—H16B0.98
C7—H7B0.98C16—H16C0.98
C7—H7C0.98S1—S21.9932 (7)
C8—H8A0.98S2—O11.4671 (13)
C8—H8B0.98S2—O21.4784 (14)
C8—H8C0.98S2—O31.4800 (12)
N3—C91.510 (2)S3—S41.9949 (7)
N3—H3M0.852 (9)S4—O61.4662 (13)
N3—H3N0.850 (9)S4—O51.4763 (13)
N3—H3O0.857 (9)S4—O41.4805 (14)
C1—N1—H1M113.5 (14)N3—C9—C12107.06 (14)
C1—N1—H1N110.2 (13)N3—C9—C10107.70 (15)
H1M—N1—H1N105.2 (19)C12—C9—C10111.08 (16)
C1—N1—H1O113.2 (13)N3—C9—C11107.84 (15)
H1M—N1—H1O107.1 (18)C12—C9—C11110.99 (16)
H1N—N1—H1O107.1 (19)C10—C9—C11111.93 (15)
N1—C1—C3107.10 (15)C9—C10—H10A109.5
N1—C1—C2106.79 (16)C9—C10—H10B109.5
C3—C1—C2111.82 (15)H10A—C10—H10B109.5
N1—C1—C4107.70 (15)C9—C10—H10C109.5
C3—C1—C4111.23 (16)H10A—C10—H10C109.5
C2—C1—C4111.89 (16)H10B—C10—H10C109.5
C1—C2—H2A109.5C9—C11—H11A109.5
C1—C2—H2B109.5C9—C11—H11B109.5
H2A—C2—H2B109.5H11A—C11—H11B109.5
C1—C2—H2C109.5C9—C11—H11C109.5
H2A—C2—H2C109.5H11A—C11—H11C109.5
H2B—C2—H2C109.5H11B—C11—H11C109.5
C1—C3—H3A109.5C9—C12—H12A109.5
C1—C3—H3B109.5C9—C12—H12B109.5
H3A—C3—H3B109.5H12A—C12—H12B109.5
C1—C3—H3C109.5C9—C12—H12C109.5
H3A—C3—H3C109.5H12A—C12—H12C109.5
H3B—C3—H3C109.5H12B—C12—H12C109.5
C1—C4—H4A109.5C13—N4—H4M112.9 (12)
C1—C4—H4B109.5C13—N4—H4N113.5 (14)
H4A—C4—H4B109.5H4M—N4—H4N105.2 (18)
C1—C4—H4C109.5C13—N4—H4O112.4 (13)
H4A—C4—H4C109.5H4M—N4—H4O105.9 (19)
H4B—C4—H4C109.5H4N—N4—H4O106.3 (19)
C5—N2—H2M110.7 (12)N4—C13—C14107.64 (15)
C5—N2—H2N113.8 (14)N4—C13—C16107.31 (14)
H2M—N2—H2N107.0 (19)C14—C13—C16111.44 (17)
C5—N2—H2O110.4 (14)N4—C13—C15107.39 (16)
H2M—N2—H2O106 (2)C14—C13—C15111.84 (15)
H2N—N2—H2O109 (2)C16—C13—C15110.96 (16)
N2—C5—C8108.05 (15)C13—C14—H14A109.5
N2—C5—C7107.26 (16)C13—C14—H14B109.5
C8—C5—C7111.22 (17)H14A—C14—H14B109.5
N2—C5—C6106.30 (16)C13—C14—H14C109.5
C8—C5—C6111.98 (18)H14A—C14—H14C109.5
C7—C5—C6111.73 (17)H14B—C14—H14C109.5
C5—C6—H6A109.5C13—C15—H15A109.5
C5—C6—H6B109.5C13—C15—H15B109.5
H6A—C6—H6B109.5H15A—C15—H15B109.5
C5—C6—H6C109.5C13—C15—H15C109.5
H6A—C6—H6C109.5H15A—C15—H15C109.5
H6B—C6—H6C109.5H15B—C15—H15C109.5
C5—C7—H7A109.5C13—C16—H16A109.5
C5—C7—H7B109.5C13—C16—H16B109.5
H7A—C7—H7B109.5H16A—C16—H16B109.5
C5—C7—H7C109.5C13—C16—H16C109.5
H7A—C7—H7C109.5H16A—C16—H16C109.5
H7B—C7—H7C109.5H16B—C16—H16C109.5
C5—C8—H8A109.5O1—S2—O2109.72 (7)
C5—C8—H8B109.5O1—S2—O3110.68 (8)
H8A—C8—H8B109.5O2—S2—O3108.91 (8)
C5—C8—H8C109.5O1—S2—S1109.40 (6)
H8A—C8—H8C109.5O2—S2—S1110.46 (6)
H8B—C8—H8C109.5O3—S2—S1107.66 (6)
C9—N3—H3M112.4 (13)O6—S4—O5111.21 (8)
C9—N3—H3N108.2 (13)O6—S4—O4109.37 (7)
H3M—N3—H3N102.8 (18)O5—S4—O4108.85 (8)
C9—N3—H3O113.2 (12)O6—S4—S3109.33 (6)
H3M—N3—H3O108.4 (18)O5—S4—S3107.44 (6)
H3N—N3—H3O111.5 (19)O4—S4—S3110.64 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1M···O4i0.85 (1)1.96 (1)2.797 (2)170 (2)
N1—H1N···O30.85 (1)1.99 (1)2.833 (2)171 (2)
N1—H1O···O50.85 (1)2.19 (1)2.934 (2)147 (2)
N2—H2M···O30.86 (1)2.09 (1)2.876 (2)150 (2)
N2—H2N···O2ii0.85 (1)1.95 (1)2.796 (2)172 (2)
N2—H2O···O50.85 (1)1.99 (1)2.832 (2)168 (2)
N3—H3M···O40.85 (1)1.99 (1)2.821 (2)164 (2)
N3—H3N···O6iii0.85 (1)1.95 (1)2.797 (2)172 (2)
N3—H3O···S1ii0.86 (1)2.55 (1)3.3491 (17)156 (2)
N4—H4M···O1iv0.86 (1)2.00 (1)2.837 (2)167 (2)
N4—H4N···O20.85 (1)2.03 (1)2.851 (2)163 (2)
N4—H4O···S3i0.85 (1)2.56 (1)3.3737 (17)160 (2)
Symmetry codes: (i) x+3/2, y1/2, z+1/2; (ii) x+1/2, y+1/2, z+1/2; (iii) x+3/2, y+1/2, z+1/2; (iv) x+1/2, y1/2, z+1/2.

Experimental details

(I)(II)
Crystal data
Chemical formula2C6H16N+·S2O322C4H12N+·S2O32
Mr316.52260.41
Crystal system, space groupMonoclinic, P21/nMonoclinic, P21/n
Temperature (K)120120
a, b, c (Å)8.6437 (3), 9.5322 (3), 21.8594 (8)11.7834 (4), 12.3519 (6), 19.9312 (8)
β (°) 95.657 (3) 97.017 (4)
V3)1792.30 (11)2879.2 (2)
Z48
Radiation typeMo KαMo Kα
µ (mm1)0.300.36
Crystal size (mm)0.42 × 0.38 × 0.310.54 × 0.12 × 0.03
Data collection
DiffractometerOxford Diffraction Xcalibur (Sapphire2, large Be window)
diffractometer
Oxford Diffraction Xcalibur (Sapphire2, large Be window)
diffractometer
Absorption correctionAnalytical
[CrysAlis PRO (Oxford Diffraction, 2010), based on expressions derived by Clark & Reid (1995)]
Analytical
[CrysAlis PRO (Oxford Diffraction, 2010), based on expressions derived by Clark & Reid (1995)]
Tmin, Tmax0.909, 0.9280.834, 0.986
No. of measured, independent and
observed [I > 2σ(I)] reflections
18736, 3162, 2858 10821, 5063, 3704
Rint0.0270.023
(sin θ/λ)max1)0.5940.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.042, 0.110, 1.09 0.034, 0.084, 0.96
No. of reflections31625063
No. of parameters196331
No. of restraints412
H-atom treatmentH atoms treated by a mixture of independent and constrained refinementH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.60, 0.260.47, 0.21

Computer programs: CrysAlis PRO (Oxford Diffraction, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), OLEX2 (Dolomanov et al., 2009) and Mercury (Macrae et al., 2008), WinGX (Farrugia, 2012) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) for (I) top
D—H···AD—HH···AD···AD—H···A
N1—H1M···O1i0.844 (10)1.952 (12)2.764 (2)161 (2)
N1—H1N···O30.853 (10)1.942 (12)2.774 (2)165 (2)
N2—H2N···O20.854 (14)1.884 (14)2.737 (2)178 (2)
N2—H2M···S1ii0.846 (10)2.548 (12)3.3688 (17)164 (2)
Symmetry codes: (i) x+1, y+1, z; (ii) x+3/2, y1/2, z+1/2.
Hydrogen-bond geometry (Å, º) for (II) top
D—H···AD—HH···AD···AD—H···A
N1—H1M···O4i0.848 (9)1.958 (10)2.797 (2)170 (2)
N1—H1N···O30.853 (9)1.988 (10)2.833 (2)171 (2)
N1—H1O···O50.845 (9)2.188 (13)2.934 (2)147.2 (17)
N2—H2M···O30.864 (9)2.094 (13)2.876 (2)150.3 (17)
N2—H2N···O2ii0.848 (9)1.953 (10)2.796 (2)172 (2)
N2—H2O···O50.853 (9)1.992 (11)2.832 (2)168 (2)
N3—H3M···O40.852 (9)1.993 (11)2.821 (2)164.0 (18)
N3—H3N···O6iii0.850 (9)1.952 (10)2.797 (2)172.0 (18)
N3—H3O···S1ii0.857 (9)2.547 (12)3.3491 (17)156.2 (17)
N4—H4M···O1iv0.856 (9)1.997 (10)2.837 (2)166.7 (17)
N4—H4N···O20.845 (9)2.033 (11)2.851 (2)162.9 (19)
N4—H4O···S3i0.852 (9)2.560 (11)3.3737 (17)160.1 (17)
Symmetry codes: (i) x+3/2, y1/2, z+1/2; (ii) x+1/2, y+1/2, z+1/2; (iii) x+3/2, y+1/2, z+1/2; (iv) x+1/2, y1/2, z+1/2.
 

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