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The title compounds, diaqua­dinitramidatolithium(I), [Li(N3O4)(H2O)2], (I), and pyridinium dinitramidate, C5H6N+·­N3O4-, (II), differ significantly in their cation-anion contacts. The Li+ atom of (I) is coordinated by two O atoms of the dinitramide anion in a chelate and by four additional water mol­ecules, with the Li and central N atom of the anion on a twofold rotation axis. The pyridinium cation of (II) exhibits a contact with the dinitramide anion via an inter­molecular N-H...N hydrogen bridge. These inter­actions are compared with those found in reported anhydrous lithium dinitramide and ammonium dinitramide salts.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270107054212/sq3109sup1.cif
Contains datablocks I, II, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270107054212/sq3109Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270107054212/sq3109IIsup3.hkl
Contains datablock II

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Portable Document Format (PDF) file https://doi.org/10.1107/S0108270107054212/sq3109sup3.pdf
Supplementary material

CCDC reference: 677079

Comment top

The potential coordination modes (Trammell et al., 1996) of dinitramide include monodentate coordination to the central N atom of the dinitramide skeleton, monodentate coordination to one O atom of the nitro groups, and bidentate coordination to two O atoms of the terminal nitro groups. We report here the molecular structures of the dinitramide salts (I) and (II), and compare (I) with its anhydrous homologue and (II) with ammonium dinitramide in terms of cation–anion contacts.

Compound (I) exhibits a distorted octahedral Li+ cation with a chelate-type coordination by two O atoms of the dinitramide anion and four additional water molecules (Fig. 1). Analogous to what was observed in the anhydrous compound, Li(N3O4) (Gilardi et al., 1997), the Li+ atom is located on a twofold rotation axis which also bisects the dinitramide anion. To the best of our knowledge, these two cases present the only examples of imposed C2 symmetry in a dinitramide. In all other cases, the dinitramide anion has C1 symmetry, except for 3,3-dinitroazetidinium, where a crystallographically imposed mirror plane passes through the dinitramide anion (Gilardi & Butcher, 1998).

The Li—O distances to the water molecules are 1.960 (4) (Li1–O3) and 2.490 (3) Å [Li1–O3ii; symmetry code: (ii) -x, 1 - y, 1 - z], whereas the distance between the Li+ atom and the O atom of the dinitramide moiety is 2.054 (4) Å. In Li(N3O4) (Gilardi et al., 1997) the five Li—O distances range from 2.028 (5) to 2.200 (2) Å and are exclusively contacts to O atoms of the dinitramide moiety. Thus, the entire packing in Li(N3O4) is based on Li—O(dinitramide) bonding. By contrast, the presence of the coordinated water in (I) allows for the formation of an approximately linear OwaterH···Odinitramide hydrogen bond which generates by translation a C(5) chain (Etter et al., 1990; Bernstein et al., 1995) running along the [100] direction (Fig. 1).

The dinitramide moiety in (I) is nearly planar, with a twist angle of 2.0°. This is a measure of the degree by which the nitro group has rotated out of the NNN plane (Pinkerton & Ritchie, 2003; Gilardi, et al. 1997) and is significantly smaller than the twist angle of 15.8° in Li(N3O4) (Gilardi et al., 1997). The dinitramide moiety has a bend angle of 1.3°, representing the pyramidalization of the nitro N atoms (expected values are 0° for ideal sp2 and 54.8° for ideal sp3 conformations), and this value is slightly smaller than the bend angle of 4.6° found in Li(N3O4).

The O···O chelate distance in (I) [2.576 (2) Å] is comparable with that reported for Li(N3O4) [2.593 Å], while the pseudotorsion angle between the two closest N—O bonds in different nitro groups in the molecule is smaller in (I) [4.4°, versus 29.6° in Li(N3O4)].

In contrast with the dinitramide coordination in (I), compound (II) exhibits an intermolecular secondary contact to the central N atom of the dinitramide moiety via an N—H···N hydrogen bond (Fig. 2). The dinitramide anion has C1 symmetry, with N—N and N—O distances comparable with those in compound (I) and other dinitramide anions (Gilardi et al., 1997; Christe et al., 1996).

The twist and bend angles of the dinitramide moiety tend, as also observed in (I), to a relatively planar conformation (twist angles 4.8 and 5.9°; bend angles 1.5 and 0.4°) and are significantly different from those in ammonium dinitramide (twist angles 25.6 and 20.8°; bend angles 5.1 and 5.3°; Gilardi et al., 1997).

The O···O distance in (II) is slightly smaller than that in the ammonium salt [2.532 (4) versus 2.591 Å, respectively] and the pseudotorsion angle is considerably smaller [9.6 versus 37.9°, respectively].

Atom N4 in the cation of (II) acts as hydrogen-bond donor to atom N1 in the anion, giving rise to an approximately linear N—H···N interaction. Since no further hydrogen bonds are present, the structure of (II) consists of isolated cation–anion pairs with no significant interactions between them. This is in contrast with ammonium dinitramide, where extensive hydrogen bonding involving all four ammonium H atoms furnishes a multi-dimensional hydrogen-bond architecture (Gilardi et al., 1997). The hydrogen bonds are directed tetrahedrally involving exclusively the O atoms of the dinitramide moiety as hydrogen-bond acceptors, with H···O distances in the range 2.153–2.230 Å.

The packing motif in (II) consists of layers lying parallel to the bc plane with different orientations of the cation–anion pairs and a distance of 3.7 Å between those layers along the a axis (Fig. 3).

Related literature top

For related literature, see: Ang et al. (2002); Bernstein et al. (1995); Christe et al. (1996); Etter et al. (1990); Gilardi & Butcher (1998); Gilardi et al. (1997); Pinkerton & Ritchie (2003); Trammell et al. (1996).

Experimental top

Compound (I) was obtained as a by-product in the preparation of a certain dinitramide salt. A mixture of trimethyltelluronium chloride (1.11 mmol) and [Ag(py)2][N3O4] (1.22 mmol) was dissolved in water (15 ml) and stirred at ambient temperature for 1 h. The resulting precipitate (AgCl) was removed by filtration and all volatile materials of the remaining solution removed in vacuo. Colourless crystals suitable for single-crystal X-ray diffraction were obtained by slow evaporation of a solution in acetone. The presence of lithium in the structure arises from impurities in the starting material [Me3Te]Cl that result from its preparation via the reaction of TeCl4 with MeLi, and was proved by 7Li NMR spectroscopy (δ -0.99 p.p.m.).

Compound (II) was obtained as a by-product in the attempted preparation of an organodinitramide with the help of [Ag(py)2][N3O4] as a dinitramide transfer reagent (Ang et al., 2002). Single crystals were grown by slow evaporation of a dichloromethane solution.

Refinement top

Water H atoms of (I) were located in a difference Fourier map and refined freely with isotropic displacement parameters. The highest peak and deepest hole in the final difference map are located 0.57 Å from N1 and 0.73 Å from N2, respectively. H atoms in (II) were placed in idealized positions and allowed to ride on their respective parent atoms, with Carom—H = 0.95 and Narom—H = 0.88 Å, and with Uiso(H) = 1.2Ueq(carrier atom). The highest peak and deepest hole in the final difference map are located 0.72 Å from H2 and 1.24 Å from C1, respectively.

Computing details top

For both compounds, data collection: CrysAlis CCD (Oxford Diffraction, 2006); cell refinement: CrysAlis RED (Oxford Diffraction, 2006); data reduction: CrysAlis RED (Oxford Diffraction, 2006); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Brandenburg, 1996); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Figures top
[Figure 1]
[Figure 2]
Fig. 1. A view of the C(5) motif chain in compound (I), running along the a axis. Hydrogen bonds and intermolecular Li···O contacts are shown as dashed lines. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radii. [Symmetry codes: (i) -x, y, 3/2 - z; (ii) -x, 1 - y, 1 - z; (iii) x, 1 - y, 1/2 + z; (iv) 1/2 - x, 1/2 - y, 2 - z; (v) -1/2 + x, 1/2 - y, -1/2 + z; (vi) -1/2 - x, 1/2 - y, 1 - z.]

Fig. 2. A view of the molecular structure of (II), showing the atom labelling scheme and the hydrogen bond (dashed line) between cation and anion. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radii.

Fig. 3. A packing diagram for (II), viewed along the a axis, with hydrogen bonds illustrated as dashed lines. Only H atoms involved in hydrogen bonds are shown. [All H atoms appear to be shown - please clarify]
(I) diaquadinitramidatolithium(I) top
Crystal data top
[Li(N3O4)(H2O)2]F(000) = 304
Mr = 148.99Dx = 1.780 (1) Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 448 reflections
a = 12.574 (5) Åθ = 3.8–30.0°
b = 7.679 (5) ŵ = 0.19 mm1
c = 6.321 (5) ÅT = 200 K
β = 114.351 (5)°Platelet, colourless
V = 556.0 (6) Å30.13 × 0.10 × 0.02 mm
Z = 4
Data collection top
Oxford Xcalibur3 CCD area-detector
diffractometer
575 independent reflections
Radiation source: fine-focus sealed tube312 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.038
Detector resolution: 15.9809 pixels mm-1θmax = 26.5°, θmin = 4.2°
ω scansh = 1215
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2006) (empirical (using intensity measurements) absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm)
k = 89
Tmin = 0.977, Tmax = 0.999l = 76
1464 measured reflections
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)] = 0.033Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.069All H-atom parameters refined
S = 1.00 w = 1/[σ2(Fo2) + (0.0332P)2]
where P = (Fo2 + 2Fc2)/3
575 reflections(Δ/σ)max < 0.001
55 parametersΔρmax = 0.20 e Å3
2 restraintsΔρmin = 0.23 e Å3
Crystal data top
[Li(N3O4)(H2O)2]V = 556.0 (6) Å3
Mr = 148.99Z = 4
Monoclinic, C2/cMo Kα radiation
a = 12.574 (5) ŵ = 0.19 mm1
b = 7.679 (5) ÅT = 200 K
c = 6.321 (5) Å0.13 × 0.10 × 0.02 mm
β = 114.351 (5)°
Data collection top
Oxford Xcalibur3 CCD area-detector
diffractometer
575 independent reflections
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2006) (empirical (using intensity measurements) absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm)
312 reflections with I > 2σ(I)
Tmin = 0.977, Tmax = 0.999Rint = 0.038
1464 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0332 restraints
wR(F2) = 0.069All H-atom parameters refined
S = 1.00Δρmax = 0.20 e Å3
575 reflectionsΔρmin = 0.23 e Å3
55 parameters
Special details top

Refinement. Details of H atom refinement: The water H atoms were located in a difference Fourier map, and freely refined with isotropic displacement parameters The highest peak and deepest hole in the final difference map were located 0.57 Å from N1 and 0.73 Å from N2, respectively.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Li10.00000.4303 (7)0.75000.0582 (17)
N10.00000.0305 (3)0.75000.0248 (6)
N20.09544 (13)0.0627 (2)0.7629 (3)0.0257 (4)
O10.17636 (10)0.03601 (16)0.7782 (2)0.0345 (4)
O20.10364 (10)0.22187 (16)0.7560 (2)0.0344 (4)
O30.10269 (15)0.5906 (2)0.6806 (3)0.0417 (5)
H10.175 (2)0.557 (3)0.703 (4)0.059 (8)*
H20.1093 (19)0.686 (4)0.730 (4)0.066 (10)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Li10.050 (3)0.025 (3)0.110 (5)0.0000.043 (3)0.000
N10.0250 (12)0.0167 (12)0.0344 (16)0.0000.0138 (12)0.000
N20.0288 (9)0.0245 (9)0.0238 (11)0.0020 (8)0.0107 (7)0.0005 (8)
O10.0311 (8)0.0295 (8)0.0443 (11)0.0098 (6)0.0169 (7)0.0013 (6)
O20.0365 (9)0.0187 (7)0.0504 (10)0.0028 (6)0.0202 (7)0.0012 (7)
O30.0374 (10)0.0220 (9)0.0663 (13)0.0009 (7)0.0220 (9)0.0002 (9)
Geometric parameters (Å, º) top
Li1—O3i1.960 (4)N1—N21.3707 (18)
Li1—O31.960 (4)N1—N2i1.3707 (18)
Li1—O2i2.054 (4)N2—O21.229 (2)
Li1—O22.054 (4)N2—O11.2403 (18)
Li1—O3ii2.490 (3)O3—Li1iii2.490 (3)
Li1—O3iii2.490 (3)O3—H10.89 (3)
Li1—Li1iv3.337 (4)O3—H20.79 (3)
Li1—Li1iii3.337 (4)
O3i—Li1—O3102.2 (3)O3iii—Li1—Li1iv148.57 (14)
O3i—Li1—O2i91.26 (8)O3i—Li1—Li1iii105.5 (2)
O3—Li1—O2i163.03 (17)O3—Li1—Li1iii47.87 (10)
O3i—Li1—O2163.03 (17)O2i—Li1—Li1iii118.69 (14)
O3—Li1—O291.26 (8)O2—Li1—Li1iii91.13 (10)
O2i—Li1—O277.6 (2)O3ii—Li1—Li1iii148.57 (15)
O3i—Li1—O3ii83.59 (10)O3iii—Li1—Li1iii35.72 (5)
O3—Li1—O3ii101.10 (11)Li1iv—Li1—Li1iii142.6 (3)
O2i—Li1—O3ii90.52 (12)N2—N1—N2i117.0 (2)
O2—Li1—O3ii83.71 (11)O2—N2—O1122.19 (16)
O3i—Li1—O3iii101.10 (11)O2—N2—N1126.98 (16)
O3—Li1—O3iii83.59 (10)O1—N2—N1110.81 (15)
O2i—Li1—O3iii83.71 (11)N2—O2—Li1135.54 (16)
O2—Li1—O3iii90.52 (12)Li1—O3—Li1iii96.41 (10)
O3ii—Li1—O3iii172.6 (3)Li1—O3—H1120.0 (14)
O3i—Li1—Li1iv47.87 (10)Li1iii—O3—H1101.0 (16)
O3—Li1—Li1iv105.5 (2)Li1—O3—H2117.7 (18)
O2i—Li1—Li1iv91.13 (10)Li1iii—O3—H2114.7 (19)
O2—Li1—Li1iv118.69 (14)H1—O3—H2106 (2)
O3ii—Li1—Li1iv35.72 (5)
N2i—N1—N2—O22.74 (14)Li1iv—Li1—O2—N281.6 (3)
N2i—N1—N2—O1178.70 (16)Li1iii—Li1—O2—N2122.0 (2)
O1—N2—O2—Li1175.83 (13)O3i—Li1—O3—Li1iii100.02 (11)
N1—N2—O2—Li15.8 (3)O2i—Li1—O3—Li1iii41.8 (5)
O3i—Li1—O2—N247.3 (6)O2—Li1—O3—Li1iii90.39 (12)
O3—Li1—O2—N2169.88 (19)O3ii—Li1—O3—Li1iii174.2 (2)
O2i—Li1—O2—N22.84 (15)O3iii—Li1—O3—Li1iii0.0
O3ii—Li1—O2—N289.1 (2)Li1iv—Li1—O3—Li1iii149.3 (2)
O3iii—Li1—O2—N286.3 (2)
Symmetry codes: (i) x, y, z+3/2; (ii) x, y+1, z+1/2; (iii) x, y+1, z+1; (iv) x, y+1, z+2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H1···O1v0.89 (3)1.96 (3)2.852 (2)173 (2)
Symmetry code: (v) x+1/2, y+1/2, z+3/2.
(II) pyridinium dinitramidate top
Crystal data top
C5H6N+·N3O4F(000) = 384
Mr = 186.13Dx = 1.585 (1) Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 868 reflections
a = 3.7009 (2) Åθ = 4.0–30.0°
b = 14.4548 (7) ŵ = 0.14 mm1
c = 14.6214 (8) ÅT = 200 K
β = 94.281 (6)°Needle, colourless
V = 780.00 (7) Å30.21 × 0.10 × 0.06 mm
Z = 4
Data collection top
Oxford Xcalibur3 CCD area-detector
diffractometer
1537 independent reflections
Radiation source: fine-focus sealed tube881 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.047
Detector resolution: 15.9809 pixels mm-1θmax = 26.0°, θmin = 4.0°
ω scansh = 42
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2006) (empirical (using intensity measurements) absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm)
k = 1717
Tmin = 0.982, Tmax = 0.995l = 1717
3991 measured reflections
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)] = 0.035Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.077H-atom parameters constrained
S = 0.98 w = 1/[σ2(Fo2) + (0.032P)2]
where P = (Fo2 + 2Fc2)/3
1537 reflections(Δ/σ)max < 0.001
118 parametersΔρmax = 0.12 e Å3
0 restraintsΔρmin = 0.17 e Å3
Crystal data top
C5H6N+·N3O4V = 780.00 (7) Å3
Mr = 186.13Z = 4
Monoclinic, P21/nMo Kα radiation
a = 3.7009 (2) ŵ = 0.14 mm1
b = 14.4548 (7) ÅT = 200 K
c = 14.6214 (8) Å0.21 × 0.10 × 0.06 mm
β = 94.281 (6)°
Data collection top
Oxford Xcalibur3 CCD area-detector
diffractometer
1537 independent reflections
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2006) (empirical (using intensity measurements) absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm)
881 reflections with I > 2σ(I)
Tmin = 0.982, Tmax = 0.995Rint = 0.047
3991 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0350 restraints
wR(F2) = 0.077H-atom parameters constrained
S = 0.98Δρmax = 0.12 e Å3
1537 reflectionsΔρmin = 0.17 e Å3
118 parameters
Special details top

Refinement. Details of H atom refinement: H atoms were placed in idealized positions and allowed to ride on their respective parent atoms, with Carom–H = 0.95 and Narom–H = 0.88 Å, and with Uiso(H) = kUeq(carrier atom), where k = 1.2 for CH. The highest peak and deepest hole in the final difference map were located 0.72 Å from H2 and 1.24 Å from C1, respectively.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.6253 (5)0.43555 (11)0.69643 (10)0.0399 (5)
N20.5614 (5)0.52747 (14)0.67356 (12)0.0447 (5)
O10.3597 (5)0.53381 (10)0.60286 (10)0.0626 (5)
O20.6900 (5)0.59413 (10)0.71511 (10)0.0680 (6)
N30.8279 (5)0.41827 (13)0.77710 (11)0.0421 (5)
O30.8931 (4)0.33517 (10)0.78669 (9)0.0567 (5)
O40.9302 (5)0.47668 (11)0.83292 (11)0.0703 (5)
N40.2594 (4)0.29446 (13)0.59717 (12)0.0409 (5)
H4A0.36360.33640.63400.049*
C10.1227 (6)0.32031 (14)0.51406 (15)0.0415 (6)
H10.13750.38300.49520.050*
C20.0385 (5)0.25588 (15)0.45651 (14)0.0424 (6)
H20.13530.27310.39690.051*
C30.0594 (6)0.16640 (15)0.48540 (16)0.0433 (6)
H30.17220.12110.44580.052*
C40.0824 (6)0.14153 (14)0.57159 (15)0.0456 (6)
H40.06760.07950.59230.055*
C50.2437 (5)0.20785 (16)0.62622 (14)0.0436 (6)
H50.34600.19200.68570.052*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0486 (12)0.0329 (10)0.0366 (11)0.0033 (8)0.0085 (10)0.0032 (8)
N20.0478 (13)0.0416 (12)0.0445 (12)0.0026 (11)0.0028 (10)0.0038 (11)
O10.0666 (12)0.0607 (11)0.0572 (11)0.0037 (9)0.0175 (10)0.0120 (9)
O20.0967 (15)0.0389 (10)0.0672 (12)0.0138 (9)0.0022 (11)0.0084 (9)
N30.0381 (12)0.0477 (13)0.0403 (12)0.0005 (10)0.0009 (10)0.0016 (10)
O30.0748 (13)0.0407 (10)0.0531 (10)0.0115 (9)0.0045 (9)0.0075 (8)
O40.0804 (13)0.0605 (10)0.0642 (11)0.0054 (10)0.0339 (10)0.0222 (9)
N40.0385 (12)0.0418 (12)0.0418 (12)0.0017 (9)0.0001 (10)0.0111 (9)
C10.0425 (14)0.0379 (13)0.0444 (14)0.0018 (11)0.0055 (12)0.0066 (12)
C20.0409 (15)0.0528 (15)0.0326 (13)0.0039 (12)0.0037 (11)0.0003 (12)
C30.0350 (14)0.0457 (15)0.0490 (15)0.0030 (11)0.0015 (12)0.0116 (12)
C40.0447 (14)0.0354 (14)0.0564 (16)0.0002 (11)0.0033 (13)0.0040 (12)
C50.0383 (15)0.0533 (15)0.0386 (13)0.0070 (12)0.0012 (12)0.0028 (13)
Geometric parameters (Å, º) top
N1—N31.372 (2)N4—H4A0.8800
N1—N21.386 (2)C1—C21.363 (3)
N2—O21.2169 (19)C1—H10.9500
N2—O11.2326 (19)C2—C31.365 (3)
N2—N11.386 (2)C2—H20.9500
N3—O41.2150 (19)C3—C41.376 (3)
N3—O31.2312 (18)C3—H30.9500
N3—N11.372 (2)C4—C51.357 (3)
N4—C51.325 (2)C4—H40.9500
N4—C11.334 (2)C5—H50.9500
N3—N1—N2117.01 (16)N4—C1—H1120.3
O2—N2—O1123.34 (19)C2—C1—H1120.3
O2—N2—N1125.82 (17)C1—C2—C3119.3 (2)
O1—N2—N1110.82 (18)C1—C2—H2120.4
O2—N2—N1125.82 (17)C3—C2—H2120.4
O1—N2—N1110.82 (18)C2—C3—C4120.31 (19)
O4—N3—O3123.56 (18)C2—C3—H3119.8
O4—N3—N1125.01 (18)C4—C3—H3119.8
O3—N3—N1111.43 (16)C5—C4—C3118.4 (2)
O4—N3—N1125.01 (18)C5—C4—H4120.8
O3—N3—N1111.43 (16)C3—C4—H4120.8
C5—N4—C1122.27 (17)N4—C5—C4120.4 (2)
C5—N4—H4A118.9N4—C5—H5119.8
C1—N4—H4A118.9C4—C5—H5119.8
N4—C1—C2119.32 (19)
N3—N1—N2—O25.6 (3)N4—C1—C2—C30.5 (3)
N3—N1—N2—O1175.99 (17)C1—C2—C3—C40.3 (3)
N2—N1—N3—O46.1 (3)C2—C3—C4—C50.4 (3)
N2—N1—N3—O3174.32 (17)C1—N4—C5—C40.5 (3)
C5—N4—C1—C20.1 (3)C3—C4—C5—N40.8 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N4—H4A···N10.881.922.794 (2)171

Experimental details

(I)(II)
Crystal data
Chemical formula[Li(N3O4)(H2O)2]C5H6N+·N3O4
Mr148.99186.13
Crystal system, space groupMonoclinic, C2/cMonoclinic, P21/n
Temperature (K)200200
a, b, c (Å)12.574 (5), 7.679 (5), 6.321 (5)3.7009 (2), 14.4548 (7), 14.6214 (8)
β (°) 114.351 (5) 94.281 (6)
V3)556.0 (6)780.00 (7)
Z44
Radiation typeMo KαMo Kα
µ (mm1)0.190.14
Crystal size (mm)0.13 × 0.10 × 0.020.21 × 0.10 × 0.06
Data collection
DiffractometerOxford Xcalibur3 CCD area-detector
diffractometer
Oxford Xcalibur3 CCD area-detector
diffractometer
Absorption correctionMulti-scan
(CrysAlis RED; Oxford Diffraction, 2006) (empirical (using intensity measurements) absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm)
Multi-scan
(CrysAlis RED; Oxford Diffraction, 2006) (empirical (using intensity measurements) absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm)
Tmin, Tmax0.977, 0.9990.982, 0.995
No. of measured, independent and
observed [I > 2σ(I)] reflections
1464, 575, 312 3991, 1537, 881
Rint0.0380.047
(sin θ/λ)max1)0.6280.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.033, 0.069, 1.00 0.035, 0.077, 0.98
No. of reflections5751537
No. of parameters55118
No. of restraints20
H-atom treatmentAll H-atom parameters refinedH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.20, 0.230.12, 0.17

Computer programs: CrysAlis CCD (Oxford Diffraction, 2006), CrysAlis RED (Oxford Diffraction, 2006), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 1997), DIAMOND (Brandenburg, 1996).

Hydrogen-bond geometry (Å, º) for (I) top
D—H···AD—HH···AD···AD—H···A
O3—H1···O1i0.89 (3)1.96 (3)2.852 (2)173 (2)
Symmetry code: (i) x+1/2, y+1/2, z+3/2.
Hydrogen-bond geometry (Å, º) for (II) top
D—H···AD—HH···AD···AD—H···A
N4—H4A···N10.881.922.794 (2)170.5
 

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