supplementary materials


HTML versionpdf versioncif file3d viewstructure factorssupplementary materialsCIF check reportsimilar papers buy article online

Acta Cryst. (2007). E63, m2194    [ doi:10.1107/S1600536807034605 ]

Bis[1,1'-(butane-1,4-diyl)diimidazolium] [delta]-octamolybdate(VI)

H.-G. Hou and J.-L. Yang

Abstract top

The title compound, (C10H16N4)2[[delta]-Mo8O26], was synthesized by a hydrothermal reaction. The structure consists of a centrosymmetric [delta]-octamolybdate anion and two 1,1'-(butane-1,4-diyl)bis(imidazolium) cations for charge balance. The anions and cations are linked by N-H...O hydrogen bonds, generating a three-dimensional supramolecular structure.

Comment top

Recently, much of work has been focused on the polyoxometalate with different neutral ligands. In this paper, the structure of the title compound, (I), is described (Fig. 1).

The compound (I) contains a centrosymmetric δ-octamolybdate anion (Allis et al., 2004; Bridgeman, 2002) and two 1,1'-(butane-1,4-diyl)bis(imidazolium) cations. As shown in Fig. 2, each cation connects three anions through hydrogen bonds (Table 2), while each anion links six cations (Fig. 3). All anions and cations are linked each other in this mode to give a three-dimensional supramolecular structure. The Mo—O bond distances and angles are in normal range (Kalpana & Vidyasagar, 2005) (Table 1).

Related literature top

For related structures, see: Allis et al. (2004); Bridgeman (2002); Kalpana & Vidyasagar (2005). For the ligand synthesis, see: Ma et al. (2003).

Experimental top

1,1'-(Butane-1,4-diyl)bis(imidazole) was synthesized according to the method reported by Ma et al. (2003). A mixture of 1,1'-(butane-1,4-diyl)bis(imidazole) (0.190 g, 0.1 mmol), Na2MoO4.2H2O (0.242 g, 1.0 mmol) and H2O (10 ml) was adjusted to pH ≈ 4 with HNO3 (1 mol L-1) and then transferred to and sealed in a 25 ml Teflon-lined stainless steel container. The container was heated to 423 K for 72 h, then cooled to room temperature. Colorless crystals of (I) were collected (yield 58.3% based on Na2MoO4.2H2O). Analysis calculated for C20H32Mo8N8O26: C 15.32, H 2.06, N 7.15%; found: C 15.30, H 2.07, N 7.18%.

Refinement top

All H atoms on C atoms were positioned geometrically and refined as riding, with C—H = 0.93 (CH), 0.97 Å (CH2) and Uiso(H) = 1.2Ueq(C). The H atoms bonded to N atoms were located on a difference Fourier map and refined isotropically with a distance restraint of 0.86 (3) Å.

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-Plus (Sheldrick, 1990); software used to prepare material for publication: SHELXL97.

Figures top
[Figure 1] Fig. 1. The structures of the anion and cation of (I). Displacement ellipsoids are drawn at the 30% probability level. H atoms have been omitted for clarity.
[Figure 2] Fig. 2. The hydrogen bonds around the 1,1'-(butane-1,4-diyl)bis(imidazole) ligand. Dashed lines denote hydrogen bonds. Only the H atoms involving hydrogen bonds have been shown. [Symmetry codes: (ii) -x + 1, -y + 1, -z + 1; (iii) -x + 3/2, y + 1/2, -z + 1/2; (iv) x, y, z - 1.]
[Figure 3] Fig. 3. The hydrogen bonds around the octamolybdate anion. Dashed lines denote hydrogen bonds. Only the H atoms involving hydrogen bonds have been shown.
Bis[1,1'-(butane-1,4-diyl)diimidazolium] δ-octamolybdate(VI) top
Crystal data top
(C10H16N4)2[Mo8O26]F(000) = 1504
Mr = 1568.06Dx = 2.530 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 10235 reflections
a = 12.252 (3) Åθ = 2.2–28.4°
b = 13.766 (3) ŵ = 2.45 mm−1
c = 12.405 (4) ÅT = 293 K
β = 100.371 (4)°Block, colourless
V = 2058.1 (9) Å30.40 × 0.32 × 0.28 mm
Z = 2
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer		4979 independent reflections
Radiation source: fine-focus sealed tube4400 reflections with I > 2σ(I)
graphiteRint = 0.022
φ and ω scansθmax = 28.4°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −16→12
Tmin = 0.405, Tmax = 0.512k = −18→16
12476 measured reflectionsl = −16→15
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)] = 0.021Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.048H atoms treated by a mixture of independent and constrained refinement
S = 1.03 w = 1/[σ2(Fo2) + (0.0222P)2 + 0.1238P]
where P = (Fo2 + 2Fc2)/3
4979 reflections(Δ/σ)max = 0.002
288 parametersΔρmax = 0.34 e Å−3
2 restraintsΔρmin = −0.63 e Å−3
Crystal data top
(C10H16N4)2[Mo8O26]V = 2058.1 (9) Å3
Mr = 1568.06Z = 2
Monoclinic, P21/nMo Kα radiation
a = 12.252 (3) ŵ = 2.45 mm−1
b = 13.766 (3) ÅT = 293 K
c = 12.405 (4) Å0.40 × 0.32 × 0.28 mm
β = 100.371 (4)°
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer		4979 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		4400 reflections with I > 2σ(I)
Tmin = 0.405, Tmax = 0.512Rint = 0.022
12476 measured reflectionsθmax = 28.4°
Refinement top
R[F2 > 2σ(F2)] = 0.021H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.048Δρmax = 0.34 e Å−3
S = 1.03Δρmin = −0.63 e Å−3
4979 reflectionsAbsolute structure: ?
288 parametersFlack parameter: ?
2 restraintsRogers parameter: ?
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Mo10.754292 (17)1.019021 (14)0.622942 (17)0.02690 (6)
Mo20.455430 (16)0.935845 (13)0.613148 (16)0.02382 (5)
Mo30.420322 (17)0.803161 (14)0.358359 (17)0.02803 (6)
Mo40.687630 (18)0.785795 (14)0.499020 (17)0.02708 (6)
O80.45559 (16)0.90491 (13)0.74631 (15)0.0406 (4)
O100.48032 (14)0.82703 (11)0.54413 (14)0.0303 (4)
O10.65759 (14)0.67556 (12)0.55209 (15)0.0354 (4)
O70.56208 (13)1.02931 (11)0.61139 (14)0.0284 (4)
O50.88155 (15)1.01901 (14)0.58946 (17)0.0419 (5)
O110.41126 (16)0.68162 (12)0.37685 (17)0.0452 (5)
O60.77946 (16)1.01455 (12)0.76203 (15)0.0380 (4)
O120.39766 (17)0.82020 (15)0.22085 (16)0.0461 (5)
O20.80695 (16)0.76876 (14)0.44952 (17)0.0436 (5)
O130.28365 (13)0.84549 (11)0.39446 (14)0.0302 (4)
O90.32230 (14)0.98175 (12)0.56067 (14)0.0320 (4)
O40.58508 (14)0.81338 (12)0.37603 (14)0.0306 (4)
N10.5128 (2)0.38184 (18)0.3352 (2)0.0499 (6)
C70.5839 (2)0.77486 (18)0.0168 (2)0.0416 (7)
H7A0.59880.7377−0.04540.050*
H7B0.50430.77510.01430.050*
C10.5719 (3)0.3377 (2)0.2674 (3)0.0499 (8)
H10.57330.27160.25230.060*
O30.71282 (15)0.88071 (11)0.60380 (14)0.0352 (4)
N30.62268 (18)0.87472 (15)0.00892 (18)0.0347 (5)
N20.60261 (18)0.49305 (14)0.27097 (18)0.0322 (5)
C80.6744 (3)0.9098 (2)−0.0680 (3)0.0476 (7)
H80.69480.8748−0.12540.057*
C90.6086 (2)0.94964 (19)0.0782 (2)0.0423 (7)
H90.57510.94520.13960.051*
C60.6404 (2)0.72714 (18)0.1215 (2)0.0384 (6)
H6A0.63940.77120.18230.046*
H6B0.71720.71430.11690.046*
C30.5309 (2)0.4750 (2)0.3355 (2)0.0420 (7)
H30.49850.52100.37480.050*
C20.6282 (3)0.4077 (2)0.2261 (3)0.0466 (7)
H20.67570.39950.17630.056*
C40.6455 (2)0.58912 (19)0.2472 (2)0.0421 (7)
H4A0.72330.58300.24220.051*
H4B0.64030.63270.30750.051*
C50.5841 (2)0.63262 (19)0.1429 (2)0.0382 (6)
H5A0.50760.64490.14930.046*
H5B0.58460.58800.08250.046*
C100.6510 (3)1.0294 (2)0.0423 (3)0.0487 (7)
H100.65241.09100.07310.058*
N40.6918 (2)1.00341 (19)−0.0483 (2)0.0517 (7)
H1N0.466 (2)0.360 (2)0.373 (2)0.063 (10)*
H4N0.724 (3)1.047 (2)−0.081 (3)0.085 (13)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Mo10.02472 (11)0.02370 (10)0.03129 (12)0.00105 (8)0.00240 (8)−0.00177 (8)
Mo20.02711 (11)0.02013 (10)0.02486 (11)−0.00093 (8)0.00640 (8)0.00104 (7)
Mo30.03107 (12)0.02043 (10)0.03198 (12)0.00099 (8)0.00405 (9)−0.00463 (8)
Mo40.03080 (12)0.02067 (10)0.03081 (12)0.00111 (8)0.00835 (9)0.00170 (8)
O80.0557 (12)0.0381 (10)0.0283 (10)−0.0024 (9)0.0080 (9)0.0029 (8)
O100.0346 (9)0.0238 (8)0.0323 (9)0.0015 (7)0.0055 (7)0.0014 (7)
O10.0393 (10)0.0226 (8)0.0469 (11)0.0027 (7)0.0150 (9)0.0044 (7)
O70.0279 (9)0.0206 (7)0.0374 (10)−0.0001 (6)0.0072 (7)−0.0023 (7)
O50.0294 (10)0.0454 (11)0.0520 (12)0.0045 (8)0.0103 (9)0.0049 (9)
O110.0467 (12)0.0237 (9)0.0649 (14)0.0004 (8)0.0087 (10)−0.0057 (9)
O60.0442 (11)0.0334 (9)0.0346 (10)−0.0002 (8)0.0021 (8)−0.0010 (8)
O120.0522 (12)0.0514 (11)0.0336 (11)0.0079 (10)0.0045 (9)−0.0056 (9)
O20.0352 (11)0.0460 (11)0.0524 (13)0.0027 (9)0.0155 (9)0.0076 (9)
O130.0270 (9)0.0230 (8)0.0398 (10)−0.0032 (7)0.0046 (7)−0.0011 (7)
O90.0301 (9)0.0344 (9)0.0331 (10)0.0027 (7)0.0100 (7)−0.0021 (7)
O40.0317 (9)0.0304 (8)0.0309 (9)0.0050 (7)0.0090 (7)−0.0013 (7)
N10.0540 (16)0.0433 (14)0.0546 (17)−0.0089 (12)0.0161 (13)0.0132 (12)
C70.0443 (17)0.0320 (13)0.0453 (17)−0.0079 (12)−0.0003 (13)0.0026 (12)
C10.058 (2)0.0252 (13)0.064 (2)−0.0010 (13)0.0045 (16)0.0032 (13)
O30.0397 (10)0.0234 (8)0.0395 (10)0.0029 (7)−0.0011 (8)−0.0007 (7)
N30.0385 (12)0.0307 (11)0.0348 (12)−0.0046 (9)0.0069 (9)0.0048 (9)
N20.0365 (12)0.0255 (10)0.0363 (12)−0.0001 (9)0.0107 (9)0.0028 (9)
C80.0488 (18)0.0539 (18)0.0417 (17)−0.0024 (14)0.0127 (14)0.0039 (14)
C90.0519 (18)0.0346 (14)0.0409 (17)−0.0032 (13)0.0097 (13)0.0012 (12)
C60.0433 (16)0.0315 (13)0.0403 (16)−0.0073 (11)0.0071 (12)0.0022 (11)
C30.0416 (16)0.0440 (16)0.0433 (17)0.0020 (13)0.0159 (13)−0.0015 (13)
C20.0534 (18)0.0331 (14)0.058 (2)0.0030 (13)0.0236 (15)−0.0082 (13)
C40.0506 (18)0.0314 (13)0.0437 (17)−0.0121 (12)0.0067 (13)0.0014 (12)
C50.0433 (16)0.0298 (13)0.0426 (16)−0.0082 (11)0.0101 (12)0.0005 (11)
C100.0542 (19)0.0342 (14)0.0522 (19)−0.0058 (13)−0.0057 (15)0.0037 (13)
N40.0512 (16)0.0470 (15)0.0561 (17)−0.0175 (13)0.0076 (13)0.0185 (13)
Geometric parameters (Å, °) top
Mo1—O51.6843 (18)C7—C61.508 (4)
Mo1—O61.6983 (18)C7—H7A0.9700
Mo1—O13i1.9249 (15)C7—H7B0.9700
Mo1—O31.9738 (16)C1—C21.339 (4)
Mo1—O9i2.3020 (18)C1—H10.9300
Mo1—O72.3377 (16)N3—C81.328 (3)
Mo2—O81.7055 (18)N3—C91.373 (3)
Mo2—O91.7611 (17)N2—C31.315 (3)
Mo2—O101.7788 (16)N2—C21.360 (3)
Mo2—O71.8367 (16)N2—C41.473 (3)
Mo3—O121.6945 (19)C8—N41.322 (4)
Mo3—O111.6952 (17)C8—H80.9300
Mo3—O131.9010 (16)C9—C101.325 (4)
Mo3—O41.9959 (17)C9—H90.9300
Mo3—O102.3128 (17)C6—C51.518 (3)
Mo3—O7i2.3403 (15)C6—H6A0.9700
Mo4—O21.7007 (18)C6—H6B0.9700
Mo4—O11.7202 (16)C3—H30.9300
Mo4—O31.8296 (17)C2—H20.9300
Mo4—O41.8331 (17)C4—C51.500 (4)
O7—Mo3i2.3403 (15)C4—H4A0.9700
O13—Mo1i1.9249 (15)C4—H4B0.9700
O9—Mo1i2.3020 (18)C5—H5A0.9700
N1—C31.302 (4)C5—H5B0.9700
N1—C11.350 (4)C10—N41.357 (4)
N1—H1N0.86 (3)C10—H100.9300
C7—N31.464 (3)N4—H4N0.86 (3)
O5—Mo1—O6104.11 (10)N3—C7—C6111.2 (2)
O5—Mo1—O13i100.84 (8)N3—C7—H7A109.4
O6—Mo1—O13i98.34 (8)C6—C7—H7A109.4
O5—Mo1—O3101.53 (8)N3—C7—H7B109.4
O6—Mo1—O394.76 (8)C6—C7—H7B109.4
O13i—Mo1—O3150.39 (7)H7A—C7—H7B108.0
O5—Mo1—O9i89.23 (8)C2—C1—N1106.6 (2)
O6—Mo1—O9i166.45 (8)C2—C1—H1126.7
O13i—Mo1—O9i81.16 (7)N1—C1—H1126.7
O3—Mo1—O9i80.00 (7)Mo4—O3—Mo1141.37 (10)
O5—Mo1—O7162.17 (8)C8—N3—C9107.9 (2)
O6—Mo1—O793.50 (8)C8—N3—C7126.3 (2)
O13i—Mo1—O773.39 (6)C9—N3—C7125.8 (2)
O3—Mo1—O779.42 (6)C3—N2—C2108.3 (2)
O9i—Mo1—O773.32 (6)C3—N2—C4126.4 (2)
O8—Mo2—O9106.68 (9)C2—N2—C4125.3 (2)
O8—Mo2—O10106.59 (8)N4—C8—N3107.6 (3)
O9—Mo2—O10110.60 (8)N4—C8—H8126.2
O8—Mo2—O7108.04 (9)N3—C8—H8126.2
O9—Mo2—O7110.97 (7)C10—C9—N3108.1 (3)
O10—Mo2—O7113.59 (7)C10—C9—H9125.9
O12—Mo3—O11105.66 (10)N3—C9—H9125.9
O12—Mo3—O13101.72 (9)C7—C6—C5111.8 (2)
O11—Mo3—O13100.88 (8)C7—C6—H6A109.3
O12—Mo3—O494.59 (9)C5—C6—H6A109.3
O11—Mo3—O498.30 (8)C7—C6—H6B109.3
O13—Mo3—O4150.33 (7)C5—C6—H6B109.3
O12—Mo3—O10161.53 (8)H6A—C6—H6B107.9
O11—Mo3—O1091.27 (8)N1—C3—N2108.5 (2)
O13—Mo3—O1081.79 (7)N1—C3—H3125.8
O4—Mo3—O1075.33 (6)N2—C3—H3125.8
O12—Mo3—O7i91.07 (8)C1—C2—N2107.1 (3)
O11—Mo3—O7i163.21 (8)C1—C2—H2126.5
O13—Mo3—O7i73.73 (6)N2—C2—H2126.5
O4—Mo3—O7i81.42 (6)N2—C4—C5112.9 (2)
O10—Mo3—O7i72.34 (6)N2—C4—H4A109.0
O2—Mo4—O1105.88 (9)C5—C4—H4A109.0
O2—Mo4—O3107.99 (9)N2—C4—H4B109.0
O1—Mo4—O3112.24 (8)C5—C4—H4B109.0
O2—Mo4—O4103.47 (9)H4A—C4—H4B107.8
O1—Mo4—O4109.84 (8)C4—C5—C6108.7 (2)
O3—Mo4—O4116.49 (7)C4—C5—H5A110.0
Mo2—O10—Mo3123.22 (8)C6—C5—H5A110.0
Mo2—O7—Mo1131.90 (8)C4—C5—H5B110.0
Mo2—O7—Mo3i137.19 (8)C6—C5—H5B110.0
Mo1—O7—Mo3i89.26 (5)H5A—C5—H5B108.3
Mo3—O13—Mo1i118.41 (8)C9—C10—N4106.6 (3)
Mo2—O9—Mo1i123.34 (8)C9—C10—H10126.7
Mo4—O4—Mo3127.22 (9)N4—C10—H10126.7
C3—N1—C1109.6 (2)C8—N4—C10109.8 (2)
C3—N1—H1N118 (2)C8—N4—H4N132 (3)
C1—N1—H1N132 (2)C10—N4—H4N118 (3)
O8—Mo2—O10—Mo3153.57 (10)O12—Mo3—O4—Mo4−170.00 (11)
O9—Mo2—O10—Mo337.97 (12)O11—Mo3—O4—Mo4−63.41 (12)
O7—Mo2—O10—Mo3−87.57 (11)O13—Mo3—O4—Mo466.47 (18)
O12—Mo3—O10—Mo252.1 (3)O10—Mo3—O4—Mo425.73 (10)
O11—Mo3—O10—Mo2−151.20 (11)O7i—Mo3—O4—Mo499.61 (11)
O13—Mo3—O10—Mo2−50.39 (10)C3—N1—C1—C20.4 (4)
O4—Mo3—O10—Mo2110.56 (10)O2—Mo4—O3—Mo161.40 (17)
O7i—Mo3—O10—Mo225.06 (9)O1—Mo4—O3—Mo1177.73 (14)
O8—Mo2—O7—Mo181.32 (13)O4—Mo4—O3—Mo1−54.42 (18)
O9—Mo2—O7—Mo1−162.05 (10)O5—Mo1—O3—Mo4−62.11 (17)
O10—Mo2—O7—Mo1−36.70 (14)O6—Mo1—O3—Mo4−167.57 (16)
O8—Mo2—O7—Mo3i−79.26 (14)O13i—Mo1—O3—Mo476.3 (2)
O9—Mo2—O7—Mo3i37.36 (15)O9i—Mo1—O3—Mo425.03 (15)
O10—Mo2—O7—Mo3i162.72 (11)O7—Mo1—O3—Mo499.74 (16)
O5—Mo1—O7—Mo2105.1 (2)C6—C7—N3—C8118.5 (3)
O6—Mo1—O7—Mo2−83.91 (12)C6—C7—N3—C9−63.8 (4)
O13i—Mo1—O7—Mo2178.43 (13)C9—N3—C8—N4−0.3 (3)
O3—Mo1—O7—Mo210.29 (11)C7—N3—C8—N4177.8 (3)
O9i—Mo1—O7—Mo292.90 (12)C8—N3—C9—C100.5 (3)
O5—Mo1—O7—Mo3i−88.0 (2)C7—N3—C9—C10−177.6 (3)
O6—Mo1—O7—Mo3i83.03 (7)N3—C7—C6—C5167.6 (2)
O13i—Mo1—O7—Mo3i−14.63 (6)C1—N1—C3—N2−1.3 (4)
O3—Mo1—O7—Mo3i177.23 (7)C2—N2—C3—N11.7 (3)
O9i—Mo1—O7—Mo3i−100.16 (6)C4—N2—C3—N1179.6 (3)
O12—Mo3—O13—Mo1i−67.03 (12)N1—C1—C2—N20.6 (4)
O11—Mo3—O13—Mo1i−175.73 (10)C3—N2—C2—C1−1.4 (3)
O4—Mo3—O13—Mo1i54.92 (18)C4—N2—C2—C1−179.3 (3)
O10—Mo3—O13—Mo1i94.55 (9)C3—N2—C4—C5−96.4 (3)
O7i—Mo3—O13—Mo1i20.64 (8)C2—N2—C4—C581.1 (3)
O8—Mo2—O9—Mo1i−155.56 (10)N2—C4—C5—C6−175.5 (2)
O10—Mo2—O9—Mo1i−40.03 (12)C7—C6—C5—C4179.3 (2)
O7—Mo2—O9—Mo1i86.98 (11)N3—C9—C10—N4−0.5 (4)
O2—Mo4—O4—Mo3160.04 (11)N3—C8—N4—C100.0 (4)
O1—Mo4—O4—Mo347.35 (12)C9—C10—N4—C80.3 (4)
O3—Mo4—O4—Mo3−81.65 (12)
Symmetry codes: (i) −x+1, −y+2, −z+1.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O1ii0.86 (3)1.98 (3)2.826 (3)171 (3)
N4—H4N···O1iii0.86 (3)2.27 (3)3.009 (3)143 (4)
N4—H4N···O6iv0.86 (3)2.22 (4)2.761 (3)121 (3)
Symmetry codes: (ii) −x+1, −y+1, −z+1; (iii) −x+3/2, y+1/2, −z+1/2; (iv) x, y, z−1.
Table 1
Selected geometric parameters (Å) top
Mo1—O51.6843 (18)Mo3—O121.6945 (19)
Mo1—O61.6983 (18)Mo3—O111.6952 (17)
Mo1—O13i1.9249 (15)Mo3—O131.9010 (16)
Mo1—O31.9738 (16)Mo3—O41.9959 (17)
Mo1—O9i2.3020 (18)Mo3—O102.3128 (17)
Mo1—O72.3377 (16)Mo3—O7i2.3403 (15)
Mo2—O81.7055 (18)Mo4—O21.7007 (18)
Mo2—O91.7611 (17)Mo4—O11.7202 (16)
Mo2—O101.7788 (16)Mo4—O31.8296 (17)
Mo2—O71.8367 (16)Mo4—O41.8331 (17)
Symmetry codes: (i) −x+1, −y+2, −z+1.
Table 2
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O1ii0.86 (3)1.98 (3)2.826 (3)171 (3)
N4—H4N···O1iii0.86 (3)2.27 (3)3.009 (3)143 (4)
N4—H4N···O6iv0.86 (3)2.22 (4)2.761 (3)121 (3)
Symmetry codes: (ii) −x+1, −y+1, −z+1; (iii) −x+3/2, y+1/2, −z+1/2; (iv) x, y, z−1.
references
References top

Allis, D. G., Rarig, R. S., Burkholder, E. & Zubieta, J. (2004). J. Mol. Struct. 688, 11–31.

Bridgeman, A. J. (2002). J. Phys. Chem. A, 106, 12151–12160.

Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.

Kalpana, G. & Vidyasagar, K. (2005). Acta Cryst. E61, m1885–m1886.

Ma, J. F., Yang, J., Zheng, G. L., Li, L. & Liu, J. F. (2003). Inorg. Chem. 42, 7531–7534.

Sheldrick, G. M. (1990). SHELXTL-Plus. Siemens Analytical X-Ray Instruments Inc., Madison, Wisconsin, USA.

Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.

Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.