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Propane-1,2-diaminium hydrogenarsenate

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aDepartment of Chemistry, University of Aberdeen, Meston Walk, Aberdeen AB24 3UE, Scotland
*Correspondence e-mail: w.harrison@abdn.ac.uk

(Received 7 September 2005; accepted 12 September 2005; online 17 September 2005)

The title compound, (C3H12N2)[AsHO4], is a mol­ecular salt containing a network of propane-1,2-diaminium cations and hydrogenarsenate anions [mean As—O 1.686 (2) Å]. The crystal packing involves cation-to-anion N—H⋯O and anion-to-anion O—H⋯O hydrogen bonds, the latter resulting in dimeric associations of two adjacent hydrogenarsenate anions.

Comment

The title compound, (I)[link] (Fig. 1[link]), was prepared as part of our ongoing structural studies of hydrogen-bonding inter­actions in protonated-amine (di)hydrogenarsenates (Todd & Harrison, 2005[Todd, M. J. & Harrison, W. T. A. (2005). Acta Cryst. E61, m1024-m1026.]).

[Scheme 1]

The [HAsO4]2− hydrogenarsenate group in (I)[link] shows its normal tetra­hedral geometry [mean As—O 1.686 (2) Å], with the protonated As1—O4 vertex showing its usual lengthening relative to the unprotonated As—O bonds (Table 1[link]). The propane-1,2-diaminium cation is disordered over two overlapped positions (Fig. 1[link]). This positional disorder manifests itself as a terminal methyl group (atoms C3 or C4) being attached to either C1 or C2, with 50% occupancy in each case. The N atoms and atoms C1 and C2 of the two orientations of the cation are not resolved. Allowing for the disorder, this ion is chiral, but crystal symmetry generates a 50:50 mix of enantiomers, which is consistent with the racemic starting material. Atoms N1 and N2 are close to being trans with respect to the C1—C2 backbone of the mol­ecule (Table 1[link]).

As well as electrostatic attractions, the component species in (I)[link] inter­act by means of a network of O—H⋯O and N—H⋯O hydrogen bonds (Table 2[link]). The (HAsO4)2− units are linked into inversion-generated dimeric pairs by way of the O4—H1⋯O2i bond (see Table 2[link] for symmetry code), with a resulting As1⋯As1i separation of 4.3963 (4) Å. This situation is distinct from that observed in related materials, where chains (Lee & Harrison, 2003[Lee, C. & Harrison, W. T. A. (2003). Acta Cryst. E59, m959-m960.]) and sheets (Wilkinson & Harrison, 2005[Wilkinson, H. S. & Harrison, W. T. A. (2005). Acta Cryst. E61, m2023-m2025.]) of (di)hydrogenarsenate ions linked by O—H⋯O bonds are seen.

In (I)[link], the organic species inter­acts with the hydrogen­arsenate dimers by way of six N—H⋯O hydrogen bonds [mean H⋯O 1.85 Å, mean N—H⋯O 170° and mean N⋯O 2.744 (3) Å]. Atoms O1, O2 and O3 accept two N—H⋯O bonds each. This hydrogen-bonding scheme results in a three-dimensional network (Fig. 2[link]).

[Figure 1]
Figure 1
A view of (I)[link], showing 50% probability displacement ellipsoids, with H atoms drawn as spheres of arbitrary radius. C-bound H atoms have been omitted for clarity and the hydrogen bond is indicated by a dashed line. Bonds to the disordered atoms C3 and C4 (see text) are shown as open lines.
[Figure 2]
Figure 2
The packing for (I)[link], with all C-bound H atoms omitted for clarity. Hydrogen bonds are indicated by dashed lines.

Experimental

Aqueous propane-1,2-diamine solution (0.5 M, 10 ml) was added to aqueous H3AsO4 solution (0.5 M, 10 ml) to result in a clear mixture. Aqueous ammonia was added to this solution to raise the pH to about 12, which is beyond the second end-point for H3AsO4 (i.e. the predominant solution species is HAsO42−). Crystals of (I)[link] grew as the water evaporated over the course of a few days.

Crystal data
  • (C3H12N2)[AsHO4]

  • Mr = 216.07

  • Monoclinic, P 21 /n

  • a = 10.9568 (4) Å

  • b = 6.4297 (3) Å

  • c = 11.5999 (5) Å

  • β = 104.816 (2)°

  • V = 790.03 (6) Å3

  • Z = 4

  • Dx = 1.817 Mg m−3

  • Mo Kα radiation

  • Cell parameters from 1952 reflections

  • θ = 2.9–27.5°

  • μ = 4.27 mm−1

  • T = 120 (2) K

  • Shard (broken from plate), colourless

  • 0.08 × 0.06 × 0.03 mm

Data collection
  • Nonius KappaCCD area-detector diffractometer

  • ω and φ scans

  • Absorption correction: multi-scan(SADABS; Bruker, 1999[Bruker (1999). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.])Tmin = 0.726, Tmax = 0.883

  • 10517 measured reflections

  • 1816 independent reflections

  • 1533 reflections with I > 2σ(I)

  • Rint = 0.051

  • θmax = 27.5°

  • h = −14 → 14

  • k = −8 → 8

  • l = −15 → 15

Refinement
  • Refinement on F2

  • R[F2 > 2σ(F2)] = 0.029

  • wR(F2) = 0.059

  • S = 1.11

  • 1816 reflections

  • 103 parameters

  • H-atom parameters constrained

  • w = 1/[σ2(Fo2) + (0.0164P)2 + 0.583P] where P = (Fo2 + 2Fc2)/3

  • (Δ/σ)max < 0.001

  • Δρmax = 0.51 e Å−3

  • Δρmin = −0.41 e Å−3

  • Extinction correction: SHELXL97 (Sheldrick, 1997[Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.])

  • Extinction coefficient: 0.0047 (7)

Table 1
Selected geometric parameters (Å, °)[link]

As1—O1 1.6642 (17)
As1—O3 1.6659 (18)
As1—O2 1.6817 (18)
As1—O4 1.7336 (18)
N1—C1—C2—N2 −164.9 (2)

Table 2
Hydrogen-bond geometry (Å, °)[link]

D—H⋯A D—H H⋯A DA D—H⋯A
O4—H1⋯O2i 0.93 1.76 2.679 (2) 170
N1—H2⋯O2ii 0.91 1.87 2.765 (3) 168
N1—H3⋯O1iii 0.91 1.83 2.738 (3) 175
N1—H4⋯O1 0.91 1.81 2.716 (3) 177
N2—H5⋯O3iv 0.91 1.82 2.713 (3) 168
N2—H6⋯O2v 0.91 1.95 2.829 (3) 162
N2—H7⋯O3vi 0.91 1.80 2.702 (3) 169
Symmetry codes: (i) -x+1, -y, -z; (ii) x, y+1, z; (iii) [-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (iv) -x+1, -y+1, -z; (v) [x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]; (vi) [x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z+{\script{1\over 2}}].

The organic cation is orientationally disordered, such that the two positions of atoms N1, N2, C1, and C2 overlap and cannot be resolved. The site-occupation factors of atoms C3 and C4 refined to 50% within experimental error and were both fixed at 0.50 for the final cycles of refinement. The O-bound H atom was found in a difference map and refined as riding in its as-found relative position. The H atoms bonded to C and N were located in idealized positions, with N—H = 0.91 Å and C—H = 0.98–0.99 Å, and refined as riding, allowing for free rotation of the –NH3 groups. The constraint Uiso(H) = 1.2Ueq(carrier) or Uiso(H) = 1.5Ueq(methyl carrier) was applied.

Data collection: COLLECT (Nonius, 1998[Nonius (1998). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: HKL SCALEPACK (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]); data reduction: HKL DENZO (Otwinowski & Minor 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]), SCALEPACK and SORTAV (Blessing 1995[Blessing, R. H. (1995). Acta Cryst. A51, 33-38.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997[Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997[Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.]); molecular graphics: ORTEP3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

The title compound, (I) (Fig. 1), was prepared as part of our ongoing structural studies of hydrogen-bonding interactions in protonated-amine (di)hydrogenarsenates (Todd & Harrison, 2005).

The (HAsO4)2− hydrogenarsenate group in (I) shows its normal tetrahedral geometry [mean As—O 1.686 (2) Å], with the protonated As1—O4 vertex showing its usual lengthening relative to the unprotonated As—O bonds (Table 1). The propane 1,2-diaminium cation is disordered over two overlapped positions (Fig. 1). This positional disorder manifests itself as a terminal methyl group (atoms C3 or C4) being attached to either C1 or C2, with 50% occupancy in each case. The N atoms and atoms C1 and C2 of the two orientations of the molecule are not resolved. Allowing for the disorder, this molecular ion is chiral, but crystal symmetry generates a 50:50 mix of enantiomers, which is consistent with the racemic starting material. Atoms N1 and N2 are close to being trans with respect to the C1—C2 backbone of the molecule (Table 1).

As well as electrostatic attractions, the component species in (I) interact by means of a network of O—H···O and N—H···O hydrogen bonds (Table 2). The (HAsO4)2− units are linked into inversion-symmetry generated dimeric pairs by way of the O4—H1···O2i bond (see Table 2 for symmetry code), with a resulting As1···As1i separation of 4.3963 (4) Å. This situation is distinct from that observed in related materials, where chains (Lee & Harrison, 2003) and sheets (Wilkinson & Harrison, 2005) of (di)hydrogenarsenate moieties linked by O—H···O bonds are seen.

In (I), the organic species interacts with the hydrogenarsenate dimers by way of six N—H···O hydrogen bonds [mean H···O 1.85 Å, mean N—H···O 170° and mean N···O 2.744 (3) Å]. Atoms O1, O2 and O3 accept two N—H···O bonds each. This hydrogen-bonding scheme results in a three-dimensional network (Fig. 2).

Experimental top

Aqueous propane 1,2-diamine solution (0.5 M, 10 ml) was added to aqueous H3AsO4 solution (0.5 M, 10 ml) to result in a clear mixture. Aqueous ammonia was added to this solution to raise the pH to about 12, which is beyond the second end-point for H3AsO4 (i.e. the predominant solution species is HAsO42−). Plate-like [Shard below?] crystals of (I) grew as the water evaporated over the course of a few days.

Refinement top

The organic cation is orientationally disordered, such that the two positions of atoms N1, N2, C1, and C2 overlap and cannot be resolved. The site-occupation factors of atoms C3 and C4 refined to 50% within experimental error and were both fixed at 0.50 for the final cycles of refinement. The O-bound H atom was found in a difference map and refined as riding in its as-found relative position. The H atoms bonded to C and N were located in idealized positions, with N—H = 0.91 Å and C—H = 0.98–0.99 Å, and refined as riding, allowing for free rotation of the –NH3 groups. The constraint Uiso(H) = 1.2Ueq(carrier) or Uiso(H) = 1.5Ueq(methyl carrier) was applied.

Computing details top

Data collection: COLLECT (Nonius, 1998); cell refinement: HKL SCALEPACK (Otwinowski & Minor, 1997); data reduction: HKL DENZO (Otwinowski & Minor 1997) and SCALEPACK and SORTAV (Blessing 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

Figures top
[Figure 1] Fig. 1. A view of (I), showing 50% probability displacement ellipsoids, with H atoms drawn as spheres of arbitrary radius. C-bound H atoms have been omitted for clarity and the hydrogen bond is indicated by a dashed line. Bonds to the disordered atoms C3 and C4 (see text) are shown as open lines.
[Figure 2] Fig. 2. The unit-cell packing for (I), with all C-bound H atoms omitted for clarity. Hydrogen bonds are indicated by dashed lines.
Propane 1,2-diaminium hydrogenarsenate top
Crystal data top
C3H12N22+·AsHO42F(000) = 440
Mr = 216.07Dx = 1.817 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 1952 reflections
a = 10.9568 (4) Åθ = 2.9–27.5°
b = 6.4297 (3) ŵ = 4.27 mm1
c = 11.5999 (5) ÅT = 120 K
β = 104.816 (2)°Shard, colourless
V = 790.03 (6) Å30.08 × 0.06 × 0.03 mm
Z = 4
Data collection top
Nonius KappaCCD area-detector
diffractometer
1816 independent reflections
Radiation source: fine-focus sealed tube1533 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.051
ω and ϕ scansθmax = 27.5°, θmin = 3.6°
Absorption correction: multi-scan
(SADABS; Bruker, 1999)
h = 1414
Tmin = 0.726, Tmax = 0.883k = 88
10517 measured reflectionsl = 1515
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: difmap (O-H) and geom (others)
R[F2 > 2σ(F2)] = 0.029H-atom parameters constrained
wR(F2) = 0.059 w = 1/[σ2(Fo2) + (0.0164P)2 + 0.583P]
where P = (Fo2 + 2Fc2)/3
S = 1.11(Δ/σ)max < 0.001
1816 reflectionsΔρmax = 0.51 e Å3
103 parametersΔρmin = 0.41 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0047 (7)
Crystal data top
C3H12N22+·AsHO42V = 790.03 (6) Å3
Mr = 216.07Z = 4
Monoclinic, P21/nMo Kα radiation
a = 10.9568 (4) ŵ = 4.27 mm1
b = 6.4297 (3) ÅT = 120 K
c = 11.5999 (5) Å0.08 × 0.06 × 0.03 mm
β = 104.816 (2)°
Data collection top
Nonius KappaCCD area-detector
diffractometer
1816 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 1999)
1533 reflections with I > 2σ(I)
Tmin = 0.726, Tmax = 0.883Rint = 0.051
10517 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0290 restraints
wR(F2) = 0.059H-atom parameters constrained
S = 1.11Δρmax = 0.51 e Å3
1816 reflectionsΔρmin = 0.41 e Å3
103 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*/UeqOcc. (<1)
As10.33664 (2)0.17853 (4)0.02271 (2)0.01169 (11)
O10.26787 (18)0.2809 (3)0.12195 (16)0.0177 (4)
O20.33133 (16)0.0828 (3)0.01944 (15)0.0151 (4)
O30.28115 (19)0.2764 (3)0.11362 (16)0.0219 (5)
O40.49363 (17)0.2485 (3)0.07736 (17)0.0216 (5)
H10.54790.19240.03550.026*
N10.3572 (2)0.6561 (3)0.2137 (2)0.0177 (5)
H20.34240.75400.15510.021*
H30.31970.69520.27180.021*
H40.32480.53190.18250.021*
N20.6919 (2)0.8345 (3)0.3314 (2)0.0175 (5)
H50.71200.80450.26180.021*
H60.72340.73380.38610.021*
H70.72580.95960.35930.021*
C10.4949 (3)0.6349 (4)0.2652 (3)0.0188 (6)
H80.53490.58190.20350.023*
H90.51100.53350.33150.023*0.50
C20.5524 (3)0.8435 (4)0.3103 (3)0.0211 (6)
H100.51760.95330.25120.025*
H110.53080.87850.38580.025*0.50
C30.4994 (6)0.4684 (10)0.3584 (6)0.0290 (15)0.50
H120.46070.34060.31950.043*0.50
H130.45300.51590.41530.043*0.50
H140.58750.44080.40070.043*0.50
C40.5312 (6)0.9222 (13)0.4236 (6)0.046 (2)0.50
H150.57211.05800.44220.069*0.50
H160.56720.82420.48800.069*0.50
H170.44040.93630.41560.069*0.50
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
As10.01350 (16)0.00989 (16)0.01258 (16)0.00009 (11)0.00497 (11)0.00047 (11)
O10.0206 (10)0.0162 (10)0.0206 (10)0.0026 (8)0.0131 (9)0.0039 (8)
O20.0184 (10)0.0087 (10)0.0181 (10)0.0007 (8)0.0044 (8)0.0016 (8)
O30.0314 (12)0.0209 (11)0.0141 (10)0.0082 (9)0.0072 (9)0.0053 (8)
O40.0130 (10)0.0235 (11)0.0298 (11)0.0049 (9)0.0084 (9)0.0116 (9)
N10.0263 (14)0.0128 (12)0.0179 (12)0.0042 (10)0.0127 (11)0.0034 (10)
N20.0247 (13)0.0122 (12)0.0141 (12)0.0017 (10)0.0021 (10)0.0009 (9)
C10.0220 (15)0.0154 (15)0.0197 (15)0.0007 (12)0.0065 (13)0.0010 (12)
C20.0236 (16)0.0177 (15)0.0218 (15)0.0019 (13)0.0052 (13)0.0035 (12)
C30.017 (3)0.025 (3)0.040 (4)0.001 (3)0.002 (3)0.019 (3)
C40.029 (4)0.067 (6)0.051 (5)0.016 (4)0.027 (4)0.030 (4)
Geometric parameters (Å, º) top
As1—O11.6642 (17)C1—C31.514 (6)
As1—O31.6659 (18)C1—C21.517 (4)
As1—O21.6817 (18)C1—H80.9900
As1—O41.7336 (18)C1—H90.9900
O4—H10.9304C2—C41.481 (7)
N1—C11.480 (4)C2—H100.9900
N1—H20.9100C2—H110.9900
N1—H30.9100C3—H120.9800
N1—H40.9100C3—H130.9800
N2—C21.486 (4)C3—H140.9800
N2—H50.9100C4—H150.9800
N2—H60.9100C4—H160.9800
N2—H70.9100C4—H170.9800
O1—As1—O3112.79 (9)C4—C2—N2104.8 (3)
O1—As1—O2113.06 (8)C4—C2—C1117.5 (4)
O3—As1—O2110.74 (9)N2—C2—C1110.0 (2)
O1—As1—O4103.11 (9)C4—C2—H10104.5
O3—As1—O4109.65 (10)N2—C2—H10109.9
O2—As1—O4107.04 (9)C1—C2—H10109.9
As1—O4—H1114.5N2—C2—H11109.3
C1—N1—H2109.5C1—C2—H11109.5
C1—N1—H3109.5H10—C2—H11108.2
H2—N1—H3109.5C1—C3—H12109.5
C1—N1—H4109.5H9—C3—H12120.5
H2—N1—H4109.5C1—C3—H13109.5
H3—N1—H4109.5H9—C3—H13112.0
C2—N2—H5109.5H12—C3—H13109.5
C2—N2—H6109.5C1—C3—H14109.5
H5—N2—H6109.5H9—C3—H1494.6
C2—N2—H7109.5H12—C3—H14109.5
H5—N2—H7109.5H13—C3—H14109.5
H6—N2—H7109.5C2—C4—H15109.5
N1—C1—C3101.4 (3)H11—C4—H15124.9
N1—C1—C2110.4 (2)C2—C4—H16109.5
C3—C1—C2116.4 (3)H11—C4—H16102.2
N1—C1—H8109.5H15—C4—H16109.5
C3—C1—H8109.5C2—C4—H17109.5
C2—C1—H8109.4H11—C4—H17100.4
N1—C1—H9109.5H15—C4—H17109.5
C2—C1—H9109.8H16—C4—H17109.5
H8—C1—H9108.2
N1—C1—C2—C475.4 (5)N1—C1—C2—N2164.9 (2)
C3—C1—C2—C439.4 (5)C3—C1—C2—N280.3 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O4—H1···O2i0.931.762.679 (2)170
N1—H2···O2ii0.911.872.765 (3)168
N1—H3···O1iii0.911.832.738 (3)175
N1—H4···O10.911.812.716 (3)177
N2—H5···O3iv0.911.822.713 (3)168
N2—H6···O2v0.911.952.829 (3)162
N2—H7···O3vi0.911.802.702 (3)169
Symmetry codes: (i) x+1, y, z; (ii) x, y+1, z; (iii) x+1/2, y+1/2, z+1/2; (iv) x+1, y+1, z; (v) x+1/2, y+1/2, z+1/2; (vi) x+1/2, y+3/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC3H12N22+·AsHO42
Mr216.07
Crystal system, space groupMonoclinic, P21/n
Temperature (K)120
a, b, c (Å)10.9568 (4), 6.4297 (3), 11.5999 (5)
β (°) 104.816 (2)
V3)790.03 (6)
Z4
Radiation typeMo Kα
µ (mm1)4.27
Crystal size (mm)0.08 × 0.06 × 0.03
Data collection
DiffractometerNonius KappaCCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 1999)
Tmin, Tmax0.726, 0.883
No. of measured, independent and
observed [I > 2σ(I)] reflections
10517, 1816, 1533
Rint0.051
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.029, 0.059, 1.11
No. of reflections1816
No. of parameters103
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.51, 0.41

Computer programs: COLLECT (Nonius, 1998), HKL SCALEPACK (Otwinowski & Minor, 1997), HKL DENZO (Otwinowski & Minor 1997) and SCALEPACK and SORTAV (Blessing 1995), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997), SHELXL97.

Selected geometric parameters (Å, º) top
As1—O11.6642 (17)As1—O21.6817 (18)
As1—O31.6659 (18)As1—O41.7336 (18)
N1—C1—C2—N2164.9 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O4—H1···O2i0.931.762.679 (2)170
N1—H2···O2ii0.911.872.765 (3)168
N1—H3···O1iii0.911.832.738 (3)175
N1—H4···O10.911.812.716 (3)177
N2—H5···O3iv0.911.822.713 (3)168
N2—H6···O2v0.911.952.829 (3)162
N2—H7···O3vi0.911.802.702 (3)169
Symmetry codes: (i) x+1, y, z; (ii) x, y+1, z; (iii) x+1/2, y+1/2, z+1/2; (iv) x+1, y+1, z; (v) x+1/2, y+1/2, z+1/2; (vi) x+1/2, y+3/2, z+1/2.
 

Acknowledgements

We thank the EPSRC National Crystallography Service (University of Southampton) for the data collection.

References

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