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Acta Cryst. (2009). E65, m1584    [ doi:10.1107/S1600536809043621 ]

trans-Bis[4-amino-N-(pyrimidin-2-yl)benzenesulfonamidato]dipyridinenickel(II) hemihydrate

Y.-F. Wang, F.-X. Li, Y. Peng, Z.-F. Chen and H. Liang

Abstract top

The asymmetric unit of the title compound, [Ni(C10H9N4O2S)2(C5H5N)2]·0.5H2O, contains the distorted octahedral trans-[Ni(sdz)2(py)2] (sdz is the sulfadiazine anion and py is pyridine) complex molecule and half of a water molecule. A three-dimensional network is generated by N-H...O and O-H...O hydrogen bonds and C-H...O interactions between the complex and the water molecules.

Comment top

The title compound consists of [Ni(C11H11N4O4S2] and 0.5 lattice water molecule. Similar to trans-[Ni(smr)2(py)2] (where smr = sulfamerazinate anion and py = pyridine) (Hossain & Amoroso, 2006), the title nickel(II) complex has a six-coordinated distorted octahedral geometry and contains two bidentate N-coordinated sulfadiazinate anions and two pyridine molecules occupying the trans sites. The coordination mode of sulfadiazine is similar to its cobalt(II) complex (Ajibade et al., 2006), but different from Zn(sdz)2 (Yuan et al., 2001) and its copper complex (Hossain et al. 2006). The Ni—N bond distances involving the sulfonamide atoms N3, N7,the pyrimido atoms N1, N5, and the pyridine atoms N9, N10, are very similar, at 2.083 (2), 2.122 (2), 2.109 (2), 2.070 (2), 2.134 (2), 2.159 (2) Å, respectively. The tetrahedral coordination at S is distorted, as in the neutral sulfadiazine molecule. A three dimensional network is generated via N—H···O and O—H···O hydrogen bonds and C—H···O interactions between the complex and water molecules.

Related literature top

For a sulfamerazine–nickel(II) complex, see: Hossain & Amoroso (2006). For sulfadiazine–metal complexes, see: Ajibade et al. (2006); Hossain et al. (2006); Yuan et al. (2001).

Experimental top

0.2 mmol Ni(NO3)2.6H2O, 0.4 mmol sulfadiazine, ethanol (2 ml) and pyridine (0.2 ml) were placed in a Pyrex tube (ca 20 cm). The tube was frozen with liquid N2, evacuated under vacuum, sealed with a torch and heated at 353 K for three days to give light-blue block-shaped crystals, with a yield of 55%.

Refinement top

The water H atoms were found in a difference Fourier map and refined freely. Other H atoms were treated as riding, with C—H distances of 0.95 Å and N—H distances of 0.88 Å, and were refined using a riding model with Uiso(H) = 1.2Ueq (C and N).

Computing details top

Data collection: CrystalClear (Rigaku, 1999); cell refinement: CrystalClear (Rigaku, 1999); data reduction: CrystalStructure (Rigaku/MSC, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure, showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. A packing plot of the title compound viewed along [001]. Hydrogen bonds are shown as dashed lines.
trans-Bis[4-amino-N-(pyrimidin-2- yl)benzenesulfonamidato]dipyridinenickel(II) hemihydrate top
Crystal data top
[Ni(C10H9N4O2S)2(C5H5N)2]·0.5H2OF(000) = 3000
Mr = 724.46Dx = 1.542 Mg m−3
Monoclinic, C2/cMo Kα radiation, λ = 0.71070 Å
Hall symbol: -C 2ycCell parameters from 10593 reflections
a = 39.593 (5) Åθ = 3.0–25.3°
b = 11.2297 (13) ŵ = 0.81 mm−1
c = 14.5656 (18) ÅT = 193 K
β = 105.463 (2)°Block, light-blue
V = 6241.6 (13) Å30.39 × 0.30 × 0.30 mm
Z = 8
Data collection top
Rigaku Mercury CCD
diffractometer		5701 independent reflections
Radiation source: fine-focus sealed tube5115 reflections with I > 2σ(I)
graphiteRint = 0.045
Detector resolution: 7.31 pixels mm-1θmax = 25.4°, θmin = 3.0°
ω scansh = −47→46
Absorption correction: multi-scan
(REQAB; Jacobson, 1998)		k = −13→13
Tmin = 0.632, Tmax = 0.784l = −15→17
29798 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)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.088H atoms treated by a mixture of independent and constrained refinement
S = 1.15 w = 1/[σ2(Fo2) + (0.0251P)2 + 12.1467P]
where P = (Fo2 + 2Fc2)/3
5701 reflections(Δ/σ)max = 0.001
434 parametersΔρmax = 0.35 e Å−3
1 restraintΔρmin = −0.37 e Å−3
Crystal data top
[Ni(C10H9N4O2S)2(C5H5N)2]·0.5H2OV = 6241.6 (13) Å3
Mr = 724.46Z = 8
Monoclinic, C2/cMo Kα radiation
a = 39.593 (5) ŵ = 0.81 mm−1
b = 11.2297 (13) ÅT = 193 K
c = 14.5656 (18) Å0.39 × 0.30 × 0.30 mm
β = 105.463 (2)°
Data collection top
Rigaku Mercury CCD
diffractometer		5701 independent reflections
Absorption correction: multi-scan
(REQAB; Jacobson, 1998)		5115 reflections with I > 2σ(I)
Tmin = 0.632, Tmax = 0.784Rint = 0.045
29798 measured reflectionsθmax = 25.4°
Refinement top
R[F2 > 2σ(F2)] = 0.043 w = 1/[σ2(Fo2) + (0.0251P)2 + 12.1467P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.088Δρmax = 0.35 e Å−3
S = 1.15Δρmin = −0.37 e Å−3
5701 reflectionsAbsolute structure: ?
434 parametersFlack parameter: ?
1 restraintRogers parameter: ?
H atoms treated by a mixture of independent and constrained refinement
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
Ni10.376495 (8)0.47975 (3)0.36660 (2)0.02041 (10)
S10.428806 (17)0.71628 (6)0.33576 (4)0.02185 (16)
S20.317022 (17)0.25094 (6)0.38453 (4)0.02043 (15)
O10.40113 (5)0.73522 (17)0.24982 (13)0.0314 (5)
O20.46403 (5)0.71068 (17)0.32506 (13)0.0297 (5)
O30.28333 (5)0.28191 (16)0.39866 (13)0.0263 (4)
O40.34354 (5)0.21802 (16)0.47017 (12)0.0267 (4)
O50.50000.8828 (3)0.25000.0490 (9)
H5A0.4897 (10)0.836 (3)0.277 (3)0.084 (16)*
N10.41630 (6)0.46846 (19)0.49554 (15)0.0217 (5)
N20.46869 (5)0.5851 (2)0.51753 (15)0.0249 (5)
N30.41832 (5)0.59728 (19)0.38171 (14)0.0212 (5)
N40.42496 (9)1.0955 (2)0.6134 (2)0.0584 (9)
H4A0.40501.13030.61320.070*
H4B0.44441.11700.65530.070*
N50.34162 (5)0.48874 (19)0.23269 (15)0.0221 (5)
N60.28946 (6)0.3704 (2)0.18929 (16)0.0268 (5)
N70.33422 (6)0.35699 (19)0.33871 (15)0.0226 (5)
N80.29208 (8)−0.1432 (3)0.1044 (2)0.0651 (10)
H8A0.3092−0.16930.08180.078*
H8B0.2711−0.17510.08500.078*
N90.40712 (6)0.34694 (19)0.32133 (15)0.0225 (5)
N100.34701 (6)0.6123 (2)0.41977 (16)0.0247 (5)
C10.43038 (7)0.4097 (2)0.57599 (18)0.0265 (6)
H10.41700.35040.59700.032*
C20.46398 (8)0.4336 (3)0.6293 (2)0.0320 (7)
H20.47440.39050.68580.038*
C30.48177 (7)0.5226 (3)0.59712 (19)0.0309 (7)
H30.50490.54080.63390.037*
C40.43644 (7)0.5526 (2)0.46787 (18)0.0203 (6)
C50.42814 (7)0.8321 (2)0.41556 (18)0.0224 (6)
C60.45869 (7)0.8664 (2)0.48213 (19)0.0266 (6)
H60.48040.82980.48250.032*
C70.45746 (8)0.9540 (3)0.5479 (2)0.0335 (7)
H70.47840.97790.59320.040*
C80.42570 (9)1.0076 (3)0.5483 (2)0.0372 (8)
C90.39532 (8)0.9720 (3)0.4813 (2)0.0375 (8)
H90.37361.00800.48110.045*
C100.39631 (8)0.8855 (2)0.4155 (2)0.0303 (7)
H100.37540.86200.37010.036*
C110.33173 (7)0.5489 (2)0.15111 (19)0.0271 (6)
H110.34620.61090.13850.033*
C120.30078 (7)0.5223 (3)0.0849 (2)0.0313 (7)
H120.29340.56410.02630.038*
C130.28092 (8)0.4319 (3)0.1077 (2)0.0328 (7)
H130.25960.41190.06230.039*
C140.31993 (7)0.4022 (2)0.24983 (18)0.0216 (6)
C150.30996 (7)0.1324 (2)0.30324 (18)0.0218 (6)
C160.27727 (8)0.0820 (3)0.2716 (2)0.0379 (8)
H160.25860.11050.29500.046*
C170.27131 (8)−0.0095 (3)0.2061 (3)0.0466 (9)
H170.2486−0.04350.18530.056*
C180.29810 (8)−0.0527 (3)0.1700 (2)0.0350 (7)
C190.33103 (8)−0.0008 (3)0.2019 (2)0.0336 (7)
H190.3498−0.02830.17820.040*
C200.33674 (7)0.0903 (3)0.2676 (2)0.0310 (7)
H200.35940.12470.28870.037*
C210.41867 (7)0.3623 (3)0.24379 (19)0.0289 (6)
H210.41280.43400.20850.035*
C220.43874 (8)0.2791 (3)0.2126 (2)0.0374 (7)
H220.44590.29260.15620.045*
C230.44820 (8)0.1763 (3)0.2645 (2)0.0330 (7)
H230.46230.11820.24510.040*
C240.43681 (8)0.1593 (3)0.3451 (2)0.0306 (7)
H240.44290.08930.38250.037*
C250.41634 (7)0.2460 (2)0.37019 (19)0.0268 (6)
H250.40830.23330.42540.032*
C260.35952 (8)0.6565 (3)0.5073 (2)0.0316 (7)
H260.38060.62340.54610.038*
C270.34397 (8)0.7466 (3)0.5450 (2)0.0362 (7)
H270.35410.77460.60780.043*
C280.31366 (8)0.7953 (3)0.4905 (2)0.0437 (8)
H280.30240.85840.51420.052*
C290.29995 (10)0.7508 (4)0.4010 (3)0.0622 (12)
H290.27870.78200.36140.075*
C300.31719 (8)0.6605 (3)0.3687 (2)0.0504 (10)
H300.30730.63080.30630.060*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.02345 (19)0.01857 (18)0.01829 (18)−0.00101 (14)0.00399 (14)0.00093 (14)
S10.0273 (4)0.0209 (3)0.0187 (3)−0.0014 (3)0.0084 (3)0.0012 (3)
S20.0248 (3)0.0191 (3)0.0181 (3)0.0005 (3)0.0070 (3)0.0016 (3)
O10.0407 (12)0.0291 (11)0.0211 (10)−0.0029 (9)0.0026 (9)0.0065 (8)
O20.0299 (11)0.0324 (11)0.0329 (11)−0.0021 (9)0.0192 (9)−0.0045 (9)
O30.0276 (10)0.0256 (10)0.0291 (10)0.0025 (8)0.0134 (9)−0.0007 (8)
O40.0317 (10)0.0270 (10)0.0192 (10)0.0024 (8)0.0027 (8)0.0043 (8)
O50.071 (3)0.033 (2)0.053 (2)0.0000.035 (2)0.000
N10.0275 (12)0.0201 (12)0.0181 (11)0.0036 (9)0.0071 (10)0.0026 (9)
N20.0216 (12)0.0291 (13)0.0231 (12)0.0032 (10)0.0042 (10)−0.0008 (10)
N30.0257 (12)0.0202 (12)0.0162 (11)0.0009 (9)0.0030 (9)0.0028 (9)
N40.090 (2)0.0377 (17)0.0558 (19)0.0075 (16)0.0342 (18)−0.0174 (15)
N50.0237 (12)0.0209 (12)0.0219 (12)0.0001 (9)0.0064 (10)0.0013 (9)
N60.0254 (12)0.0299 (13)0.0231 (12)−0.0027 (10)0.0031 (10)0.0037 (10)
N70.0275 (12)0.0194 (12)0.0192 (11)−0.0035 (9)0.0032 (10)0.0029 (9)
N80.0504 (18)0.076 (2)0.078 (2)−0.0238 (17)0.0320 (17)−0.0562 (19)
N90.0258 (12)0.0209 (12)0.0202 (11)−0.0040 (9)0.0053 (10)0.0000 (9)
N100.0249 (12)0.0242 (12)0.0254 (13)−0.0023 (10)0.0076 (10)0.0009 (10)
C10.0355 (16)0.0254 (15)0.0208 (14)0.0074 (12)0.0110 (13)0.0042 (12)
C20.0341 (16)0.0401 (17)0.0213 (15)0.0132 (14)0.0064 (13)0.0082 (13)
C30.0223 (14)0.0453 (18)0.0225 (15)0.0061 (13)0.0016 (12)−0.0034 (13)
C40.0257 (14)0.0174 (13)0.0189 (13)0.0031 (11)0.0079 (11)−0.0020 (11)
C50.0318 (15)0.0169 (13)0.0208 (14)−0.0008 (11)0.0111 (12)0.0026 (11)
C60.0329 (16)0.0216 (14)0.0267 (15)0.0010 (12)0.0103 (13)0.0024 (12)
C70.0480 (19)0.0260 (16)0.0256 (15)0.0008 (14)0.0082 (14)−0.0013 (13)
C80.065 (2)0.0203 (15)0.0359 (17)0.0015 (15)0.0303 (17)0.0018 (13)
C90.0407 (18)0.0240 (16)0.057 (2)0.0090 (14)0.0297 (17)0.0065 (15)
C100.0314 (16)0.0193 (14)0.0429 (18)0.0021 (12)0.0146 (14)0.0045 (13)
C110.0325 (16)0.0257 (15)0.0247 (15)0.0014 (12)0.0101 (13)0.0058 (12)
C120.0333 (16)0.0382 (17)0.0207 (14)0.0028 (14)0.0042 (13)0.0115 (13)
C130.0283 (15)0.0400 (18)0.0254 (15)−0.0014 (14)−0.0013 (13)0.0026 (14)
C140.0242 (14)0.0195 (14)0.0215 (14)0.0010 (11)0.0070 (11)0.0001 (11)
C150.0254 (14)0.0218 (14)0.0181 (13)0.0005 (11)0.0056 (11)0.0003 (11)
C160.0317 (16)0.0361 (18)0.053 (2)−0.0107 (14)0.0232 (15)−0.0177 (15)
C170.0335 (17)0.052 (2)0.061 (2)−0.0178 (16)0.0235 (17)−0.0289 (18)
C180.0387 (17)0.0328 (17)0.0348 (17)−0.0049 (14)0.0122 (14)−0.0100 (14)
C190.0313 (16)0.0405 (18)0.0322 (16)0.0001 (14)0.0140 (13)−0.0129 (14)
C200.0231 (14)0.0376 (17)0.0321 (16)−0.0033 (13)0.0070 (13)−0.0079 (14)
C210.0405 (17)0.0268 (15)0.0192 (14)0.0010 (13)0.0076 (13)0.0043 (12)
C220.0501 (19)0.0391 (18)0.0300 (17)0.0010 (15)0.0226 (15)0.0003 (14)
C230.0369 (17)0.0302 (16)0.0352 (17)0.0046 (13)0.0151 (14)−0.0029 (14)
C240.0389 (17)0.0239 (15)0.0295 (16)0.0050 (13)0.0098 (13)0.0036 (12)
C250.0360 (16)0.0243 (15)0.0228 (14)−0.0005 (12)0.0124 (13)0.0033 (12)
C260.0328 (16)0.0324 (17)0.0293 (16)0.0060 (13)0.0080 (13)−0.0005 (13)
C270.0377 (17)0.0398 (18)0.0323 (17)0.0043 (15)0.0115 (14)−0.0072 (14)
C280.0415 (19)0.042 (2)0.049 (2)0.0133 (16)0.0139 (16)−0.0086 (16)
C290.052 (2)0.078 (3)0.046 (2)0.041 (2)−0.0041 (18)−0.016 (2)
C300.0371 (19)0.065 (2)0.041 (2)0.0211 (17)−0.0049 (16)−0.0147 (18)
Geometric parameters (Å, °) top
Ni1—N52.070 (2)C6—C71.384 (4)
Ni1—N32.083 (2)C6—H60.9500
Ni1—N12.109 (2)C7—C81.395 (4)
Ni1—N72.122 (2)C7—H70.9500
Ni1—N92.134 (2)C8—C91.390 (5)
Ni1—N102.159 (2)C9—C101.372 (4)
S1—O11.443 (2)C9—H90.9500
S1—O21.4454 (19)C10—H100.9500
S1—N31.598 (2)C11—C121.375 (4)
S1—C51.749 (3)C11—H110.9500
S2—O31.4455 (19)C12—C131.377 (4)
S2—O41.4480 (19)C12—H120.9500
S2—N71.603 (2)C13—H130.9500
S2—C151.754 (3)C15—C161.375 (4)
O5—H5A0.83 (4)C15—C201.383 (4)
N1—C11.331 (3)C16—C171.379 (4)
N1—C41.365 (3)C16—H160.9500
N2—C31.336 (3)C17—C181.391 (4)
N2—C41.339 (3)C17—H170.9500
N3—C41.364 (3)C18—C191.390 (4)
N4—C81.374 (4)C19—C201.377 (4)
N4—H4A0.8800C19—H190.9500
N4—H4B0.8800C20—H200.9500
N5—C111.332 (3)C21—C221.380 (4)
N5—C141.363 (3)C21—H210.9500
N6—C131.337 (4)C22—C231.376 (4)
N6—C141.339 (3)C22—H220.9500
N7—C141.365 (3)C23—C241.379 (4)
N8—C181.371 (4)C23—H230.9500
N8—H8A0.8800C24—C251.378 (4)
N8—H8B0.8800C24—H240.9500
N9—C251.337 (3)C25—H250.9500
N9—C211.338 (3)C26—C271.373 (4)
N10—C301.331 (4)C26—H260.9500
N10—C261.334 (4)C27—C281.364 (4)
C1—C21.376 (4)C27—H270.9500
C1—H10.9500C28—C291.367 (5)
C2—C31.375 (4)C28—H280.9500
C2—H20.9500C29—C301.373 (5)
C3—H30.9500C29—H290.9500
C5—C61.388 (4)C30—H300.9500
C5—C101.396 (4)
N5—Ni1—N3112.36 (8)C6—C7—H7119.7
N5—Ni1—N1173.86 (8)C8—C7—H7119.7
N3—Ni1—N163.88 (8)N4—C8—C9121.2 (3)
N5—Ni1—N763.73 (8)N4—C8—C7119.8 (3)
N3—Ni1—N7174.89 (8)C9—C8—C7119.0 (3)
N1—Ni1—N7119.69 (8)C10—C9—C8120.9 (3)
N5—Ni1—N991.96 (8)C10—C9—H9119.5
N3—Ni1—N988.53 (8)C8—C9—H9119.5
N1—Ni1—N983.22 (8)C9—C10—C5119.8 (3)
N7—Ni1—N988.34 (8)C9—C10—H10120.1
N5—Ni1—N1090.90 (8)C5—C10—H10120.1
N3—Ni1—N1090.92 (8)N5—C11—C12120.7 (3)
N1—Ni1—N1093.96 (8)N5—C11—H11119.7
N7—Ni1—N1092.41 (8)C12—C11—H11119.7
N9—Ni1—N10177.09 (8)C11—C12—C13116.8 (3)
O1—S1—O2116.38 (12)C11—C12—H12121.6
O1—S1—N3105.35 (11)C13—C12—H12121.6
O2—S1—N3112.00 (12)N6—C13—C12124.7 (3)
O1—S1—C5108.93 (12)N6—C13—H13117.6
O2—S1—C5106.85 (12)C12—C13—H13117.6
N3—S1—C5106.97 (11)N6—C14—N5124.8 (2)
O3—S2—O4115.06 (11)N6—C14—N7126.7 (2)
O3—S2—N7113.02 (11)N5—C14—N7108.5 (2)
O4—S2—N7104.92 (11)C16—C15—C20118.8 (3)
O3—S2—C15106.95 (12)C16—C15—S2120.4 (2)
O4—S2—C15109.65 (12)C20—C15—S2120.9 (2)
N7—S2—C15106.97 (12)C15—C16—C17120.7 (3)
C1—N1—C4117.6 (2)C15—C16—H16119.6
C1—N1—Ni1148.4 (2)C17—C16—H16119.6
C4—N1—Ni192.99 (15)C16—C17—C18121.0 (3)
C3—N2—C4114.8 (2)C16—C17—H17119.5
C4—N3—S1124.13 (18)C18—C17—H17119.5
C4—N3—Ni194.16 (15)N8—C18—C19121.1 (3)
S1—N3—Ni1140.67 (12)N8—C18—C17120.9 (3)
C8—N4—H4A120.0C19—C18—C17118.0 (3)
C8—N4—H4B120.0C20—C19—C18120.6 (3)
H4A—N4—H4B120.0C20—C19—H19119.7
C11—N5—C14118.4 (2)C18—C19—H19119.7
C11—N5—Ni1146.01 (19)C19—C20—C15121.0 (3)
C14—N5—Ni195.00 (15)C19—C20—H20119.5
C13—N6—C14114.7 (2)C15—C20—H20119.5
C14—N7—S2123.83 (18)N9—C21—C22123.2 (3)
C14—N7—Ni192.64 (15)N9—C21—H21118.4
S2—N7—Ni1143.48 (13)C22—C21—H21118.4
C18—N8—H8A120.0C23—C22—C21118.9 (3)
C18—N8—H8B120.0C23—C22—H22120.5
H8A—N8—H8B120.0C21—C22—H22120.5
C25—N9—C21116.9 (2)C22—C23—C24118.8 (3)
C25—N9—Ni1121.68 (18)C22—C23—H23120.6
C21—N9—Ni1121.38 (18)C24—C23—H23120.6
C30—N10—C26115.5 (3)C25—C24—C23118.5 (3)
C30—N10—Ni1124.3 (2)C25—C24—H24120.7
C26—N10—Ni1120.04 (18)C23—C24—H24120.7
N1—C1—C2121.0 (3)N9—C25—C24123.7 (3)
N1—C1—H1119.5N9—C25—H25118.2
C2—C1—H1119.5C24—C25—H25118.2
C3—C2—C1117.1 (3)N10—C26—C27124.4 (3)
C3—C2—H2121.4N10—C26—H26117.8
C1—C2—H2121.4C27—C26—H26117.8
N2—C3—C2124.2 (3)C28—C27—C26118.8 (3)
N2—C3—H3117.9C28—C27—H27120.6
C2—C3—H3117.9C26—C27—H27120.6
N2—C4—N3126.1 (2)C27—C28—C29118.2 (3)
N2—C4—N1125.2 (2)C27—C28—H28120.9
N3—C4—N1108.7 (2)C29—C28—H28120.9
C6—C5—C10120.0 (3)C28—C29—C30119.3 (3)
C6—C5—S1120.4 (2)C28—C29—H29120.4
C10—C5—S1119.5 (2)C30—C29—H29120.4
C7—C6—C5119.7 (3)N10—C30—C29123.9 (3)
C7—C6—H6120.1N10—C30—H30118.1
C5—C6—H6120.1C29—C30—H30118.1
C6—C7—C8120.5 (3)
N3—Ni1—N1—C1−169.1 (4)S1—N3—C4—N1165.80 (17)
N7—Ni1—N1—C16.7 (4)Ni1—N3—C4—N1−4.7 (2)
N9—Ni1—N1—C1−77.5 (3)C1—N1—C4—N2−3.4 (4)
N10—Ni1—N1—C1101.8 (3)Ni1—N1—C4—N2−175.2 (2)
N3—Ni1—N1—C4−3.18 (14)C1—N1—C4—N3176.4 (2)
N7—Ni1—N1—C4172.69 (14)Ni1—N1—C4—N34.6 (2)
N9—Ni1—N1—C488.51 (15)O1—S1—C5—C6−151.9 (2)
N10—Ni1—N1—C4−92.26 (15)O2—S1—C5—C6−25.5 (2)
O1—S1—N3—C4−175.1 (2)N3—S1—C5—C694.6 (2)
O2—S1—N3—C457.5 (2)O1—S1—C5—C1031.7 (2)
C5—S1—N3—C4−59.3 (2)O2—S1—C5—C10158.2 (2)
O1—S1—N3—Ni1−10.2 (2)N3—S1—C5—C10−81.7 (2)
O2—S1—N3—Ni1−137.63 (18)C10—C5—C6—C7−0.4 (4)
C5—S1—N3—Ni1105.6 (2)S1—C5—C6—C7−176.7 (2)
N5—Ni1—N3—C4−171.50 (14)C5—C6—C7—C80.5 (4)
N1—Ni1—N3—C43.18 (14)C6—C7—C8—N4−179.3 (3)
N9—Ni1—N3—C4−79.99 (15)C6—C7—C8—C9−0.3 (4)
N10—Ni1—N3—C497.15 (15)N4—C8—C9—C10179.0 (3)
N5—Ni1—N3—S121.0 (2)C7—C8—C9—C100.0 (4)
N1—Ni1—N3—S1−164.3 (2)C8—C9—C10—C50.1 (4)
N9—Ni1—N3—S1112.5 (2)C6—C5—C10—C90.1 (4)
N10—Ni1—N3—S1−70.4 (2)S1—C5—C10—C9176.5 (2)
N3—Ni1—N5—C11−11.8 (4)C14—N5—C11—C12−1.6 (4)
N7—Ni1—N5—C11171.8 (4)Ni1—N5—C11—C12−169.5 (2)
N9—Ni1—N5—C11−101.0 (3)N5—C11—C12—C130.4 (4)
N10—Ni1—N5—C1179.6 (3)C14—N6—C13—C12−0.7 (4)
N3—Ni1—N5—C14178.81 (14)C11—C12—C13—N60.8 (5)
N7—Ni1—N5—C142.42 (14)C13—N6—C14—N5−0.7 (4)
N9—Ni1—N5—C1489.60 (15)C13—N6—C14—N7177.7 (3)
N10—Ni1—N5—C14−89.82 (16)C11—N5—C14—N61.8 (4)
O3—S2—N7—C14−63.8 (2)Ni1—N5—C14—N6175.1 (2)
O4—S2—N7—C14170.0 (2)C11—N5—C14—N7−176.8 (2)
C15—S2—N7—C1453.6 (2)Ni1—N5—C14—N7−3.6 (2)
O3—S2—N7—Ni1112.9 (2)S2—N7—C14—N62.9 (4)
O4—S2—N7—Ni1−13.2 (2)Ni1—N7—C14—N6−175.1 (2)
C15—S2—N7—Ni1−129.7 (2)S2—N7—C14—N5−178.49 (18)
N5—Ni1—N7—C14−2.41 (14)Ni1—N7—C14—N53.5 (2)
N1—Ni1—N7—C14−176.65 (14)O3—S2—C15—C16−4.6 (3)
N9—Ni1—N7—C14−95.42 (15)O4—S2—C15—C16120.8 (2)
N10—Ni1—N7—C1487.40 (15)N7—S2—C15—C16−126.0 (2)
N5—Ni1—N7—S2−179.7 (3)O3—S2—C15—C20173.3 (2)
N1—Ni1—N7—S26.1 (3)O4—S2—C15—C20−61.3 (3)
N9—Ni1—N7—S287.3 (2)N7—S2—C15—C2052.0 (3)
N10—Ni1—N7—S2−89.9 (2)C20—C15—C16—C170.6 (5)
N5—Ni1—N9—C25−129.8 (2)S2—C15—C16—C17178.6 (3)
N3—Ni1—N9—C25117.9 (2)C15—C16—C17—C18−0.4 (5)
N1—Ni1—N9—C2554.0 (2)C16—C17—C18—N8−179.6 (3)
N7—Ni1—N9—C25−66.1 (2)C16—C17—C18—C190.0 (5)
N5—Ni1—N9—C2151.8 (2)N8—C18—C19—C20179.8 (3)
N3—Ni1—N9—C21−60.5 (2)C17—C18—C19—C200.3 (5)
N1—Ni1—N9—C21−124.4 (2)C18—C19—C20—C15−0.1 (5)
N7—Ni1—N9—C21115.5 (2)C16—C15—C20—C19−0.3 (4)
N5—Ni1—N10—C303.0 (3)S2—C15—C20—C19−178.3 (2)
N3—Ni1—N10—C30115.4 (3)C25—N9—C21—C221.0 (4)
N1—Ni1—N10—C30179.2 (3)Ni1—N9—C21—C22179.5 (2)
N7—Ni1—N10—C30−60.8 (3)N9—C21—C22—C23−1.6 (5)
N5—Ni1—N10—C26−172.8 (2)C21—C22—C23—C241.0 (5)
N3—Ni1—N10—C26−60.4 (2)C22—C23—C24—C250.1 (4)
N1—Ni1—N10—C263.4 (2)C21—N9—C25—C240.2 (4)
N7—Ni1—N10—C26123.4 (2)Ni1—N9—C25—C24−178.3 (2)
C4—N1—C1—C20.2 (4)C23—C24—C25—N9−0.8 (4)
Ni1—N1—C1—C2164.4 (3)C30—N10—C26—C27−0.9 (4)
N1—C1—C2—C31.8 (4)Ni1—N10—C26—C27175.3 (2)
C4—N2—C3—C2−1.7 (4)N10—C26—C27—C280.1 (5)
C1—C2—C3—N2−1.0 (4)C26—C27—C28—C290.7 (5)
C3—N2—C4—N3−175.7 (2)C27—C28—C29—C30−0.7 (6)
C3—N2—C4—N14.1 (4)C26—N10—C30—C290.8 (5)
S1—N3—C4—N2−14.4 (4)Ni1—N10—C30—C29−175.2 (3)
Ni1—N3—C4—N2175.1 (2)C28—C29—C30—N100.0 (7)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N8—H8B···O3i0.882.283.091 (3)153
N8—H8A···O4ii0.882.443.287 (3)161
N4—H4B···O5iii0.882.263.113 (4)162
N4—H4A···O1iv0.882.543.075 (3)120
O5—H5A···O20.83 (4)1.97 (4)2.791 (3)172 (4)
C2—H2···O2v0.952.453.280 (3)145
C12—H12···O3vi0.952.493.417 (3)165
Symmetry codes: (i) −x+1/2, y−1/2, −z+1/2; (ii) x, −y, z−1/2; (iii) −x+1, −y+2, −z+1; (iv) x, −y+2, z+1/2; (v) x, −y+1, z+1/2; (vi) x, −y+1, z−1/2.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N8—H8B···O3i0.882.283.091 (3)153
N8—H8A···O4ii0.882.443.287 (3)161
N4—H4B···O5iii0.882.263.113 (4)162
N4—H4A···O1iv0.882.543.075 (3)120
O5—H5A···O20.83 (4)1.97 (4)2.791 (3)172 (4)
C2—H2···O2v0.952.453.280 (3)145
C12—H12···O3vi0.952.493.417 (3)165
Symmetry codes: (i) −x+1/2, y−1/2, −z+1/2; (ii) x, −y, z−1/2; (iii) −x+1, −y+2, −z+1; (iv) x, −y+2, z+1/2; (v) x, −y+1, z+1/2; (vi) x, −y+1, z−1/2.
Acknowledgements top

The authors thank the National Natural Science Foundation of China (No. 20861002), the 973 Plan of China (2009CB526503), the Natural Science Foundation of Guangxi Province of China (No. 0991003) and the Open Foundation of the Key Laboratory for the Chemistry and Molecular Engineering of Medicinal Resources (Ministry of Education of China) for financial support.

references
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