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Acta Cryst. (2007). E63, m1971    [ doi:10.1107/S1600536807029741 ]

Bis(2,2'-diamino-4,4'-bi-1,3-thiazole-[kappa]2N,N')(2-nitrobenzoato-[kappa]2O,O')nickel(II) 2-nitrobenzoate

B.-X. Liu, G.-H. Chen, Y.-Y. Lin and Y.-P. Yu

Abstract top

The crystal structure of the title compound, [Ni(C7H4NO4)(C6H6N4S2)2](C7H4NO4), consists of NiII complex cations and 2-nitrobenzoate anions. The NiII ion assumes a distorted octahedral coordination geometry formed by one 2-nitrobenzoate anion and two diaminobithiazole ligands. N-H...O hydrogen bonding between cations and anions and between cations helps to stabilize the crystal structure.

Comment top

Transition metal complexes of 2,2'-diamino-4,4'-bi-1,3-thiazole (DABT) have shown potential application in the field of soft magnetic material (Liu et al., 2001). As part of serial structural investigation of metal complexes with DABT (Liu & Xu, 2004), the title NiII complex was recently prepared and its X-ray structure is presented here.

The molecular structure of the title compound is shown in Fig. 1. The Ni ion has a distorted octahedral coordinatation geometry formed by one 2-nitrobenzoate anion and two DABT ligands. Within the complex, two DABT moieties are approximately perpendicular to each other with a dihedral angle of 81.23 (7)°. This is comparable to 84.3 (4)° found in a NiII complex of DABT reported previously (Liu & Xu, 2003). Each DABT moiety is approximately coplanar coordinated to Ni atom, the dihedral angles between two thiazole rings being 6.2 (3) and 2.6 (2)°, respectively, which agree with 4.57 (7)° found in [Mn(DABT)(oxydiacetate)] (Luo et al., 2004). The average Ni—N bond distance (Table 1) is shorter than the value of 2.113 (2) Å of average Ni—N bond distance found in reported NiII complex of DABT (Liu & Xu, 2003).

The extensive hydrogen bonding occurs in the crystal structure (Table 2). While 2-nitrobenzoate anion links with complex cation via N—H···O hydrogen bonding, the N—H···O hydrogen bonding is also observed between complex cations. They help to stabilize the crystal structure.

Related literature top

For general background, see Liu et al. (2001); Liu & Xu (2004). For related structures, see Liu & Xu (2003); Luo et al. (2004).

Experimental top

An ethanol solution (20 ml) containing DABT (0.20 g, 1 mmol) and NiCl2·6H2O (0.24 g, 1 mmol) was mixed with an aqueous solution (10 ml) of 2-nitrobenzoic acid (0.34 g, 2 mmol) and NaOH (0.08 g, 2 mmol). The mixture was refluxed for 6 h. After cooling to room temperature the solution was filtered. Single crystals of the title compound were obtained from the filtrate after 4 d.

Refinement top

H atoms on carbon atoms were placed in calculated positions, with C—H distances = 0.93 Å (aromatic), and were included in the final cycles of refinement in riding mode with Uiso(H) = 1.2Ueq(C). Amino H atoms were located in a difference Fourier map and included in the structure factor calculations with fixed positional and isotropic displacement parameters Uiso(H) = 0.05 Å2.

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC & Rigaku, 2002); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I) with 30% probability displacement ellipsoids (arbitrary spheres for H atoms), dashed lines showing the hydrogen bonding [symmetry code: (i) x, y, z − 1].
Bis(2,2'-diamino-4,4'-bi-1,3-thiazole-κ2N,N')(2-nitrobenzoato-\ κ2O,O')nickel(II) 2-nitrobenzoate top
Crystal data top
[Ni(C7H4NO4)(C6H6N4S2)2](C7H4NO4)F000 = 1608
Mr = 787.47Dx = 1.612 Mg m−3
Monoclinic, P21/nMo Kα radiation
λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 5670 reflections
a = 15.1514 (18) Åθ = 2.0–25.0º
b = 13.5905 (16) ŵ = 0.92 mm−1
c = 16.4702 (19) ÅT = 295 (2) K
β = 106.901 (2)ºPrism, green
V = 3245.0 (7) Å30.20 × 0.17 × 0.14 mm
Z = 4
Data collection top
Rigaku R-AXIS RAPID IP
diffractometer		5721 independent reflections
Radiation source: fine-focus sealed tube3217 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.086
Detector resolution: 10.0 pixels mm-1θmax = 25.0º
T = 295(2) Kθmin = 1.9º
ω scansh = −16→18
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)		k = −8→16
Tmin = 0.812, Tmax = 0.880l = −18→19
16530 measured reflections
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.055  w = 1/[σ2(Fo2) + (0.0399P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.123(Δ/σ)max < 0.001
S = 1.00Δρmax = 0.42 e Å−3
5721 reflectionsΔρmin = −0.37 e Å−3
443 parametersExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0016 (3)
Secondary atom site location: difference Fourier map
Crystal data top
[Ni(C7H4NO4)(C6H6N4S2)2](C7H4NO4)V = 3245.0 (7) Å3
Mr = 787.47Z = 4
Monoclinic, P21/nMo Kα
a = 15.1514 (18) ŵ = 0.92 mm−1
b = 13.5905 (16) ÅT = 295 (2) K
c = 16.4702 (19) Å0.20 × 0.17 × 0.14 mm
β = 106.901 (2)º
Data collection top
Rigaku R-AXIS RAPID IP
diffractometer		5721 independent reflections
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)		3217 reflections with I > 2σ(I)
Tmin = 0.812, Tmax = 0.880Rint = 0.086
16530 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.055443 parameters
wR(F2) = 0.123H-atom parameters constrained
S = 1.00Δρmax = 0.42 e Å−3
5721 reflectionsΔρmin = −0.37 e Å−3
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
Ni0.63304 (4)0.33644 (5)0.24108 (4)0.0312 (2)
N110.5040 (2)0.2921 (3)0.1665 (2)0.0331 (10)
N120.4906 (3)0.1244 (3)0.1911 (3)0.0561 (13)
H12A0.45770.08320.19570.050*
H12B0.54020.12540.22910.050*
N130.5856 (3)0.4680 (3)0.1795 (2)0.0360 (10)
N140.7079 (3)0.5816 (3)0.2175 (3)0.0592 (13)
H14A0.74060.63550.20390.050*
H14B0.74470.53460.24640.050*
N210.7605 (3)0.3845 (3)0.3162 (2)0.0342 (10)
N220.7372 (3)0.4610 (3)0.4359 (3)0.0560 (13)
H22A0.67800.45160.42080.050*
H22B0.76100.49780.48390.050*
N230.7148 (2)0.2931 (3)0.1671 (2)0.0333 (10)
N240.6186 (3)0.2242 (3)0.0405 (2)0.0513 (13)
H24A0.57880.23300.06640.050*
H24B0.60090.1984−0.00800.050*
N310.6342 (4)0.0406 (4)0.4158 (3)0.0608 (14)
N410.8469 (4)0.0572 (5)0.8500 (4)0.0764 (17)
O310.5826 (2)0.3387 (3)0.34990 (19)0.0382 (8)
O320.6516 (2)0.2056 (2)0.3248 (2)0.0390 (9)
O330.5692 (3)0.0173 (3)0.3555 (3)0.0813 (14)
O340.7105 (4)0.0015 (3)0.4328 (3)0.0918 (15)
O410.8915 (4)0.0340 (4)0.8015 (4)0.125 (2)
O420.8355 (4)0.0051 (4)0.9037 (4)0.121 (2)
O430.6322 (3)0.0242 (3)0.8000 (2)0.0693 (12)
O440.6394 (2)0.0765 (3)0.9281 (2)0.0442 (9)
S110.34324 (9)0.22051 (12)0.09485 (10)0.0619 (5)
S120.54644 (11)0.63624 (11)0.10792 (10)0.0639 (5)
S210.90877 (10)0.45038 (12)0.42205 (9)0.0605 (5)
S220.80094 (10)0.22774 (12)0.06398 (9)0.0600 (5)
C110.4490 (3)0.3681 (4)0.1231 (3)0.0394 (13)
C120.3624 (3)0.3435 (4)0.0819 (3)0.0579 (16)
H120.31820.38700.05030.070*
C130.4568 (3)0.2098 (4)0.1580 (3)0.0377 (13)
C140.4950 (3)0.4635 (4)0.1267 (3)0.0400 (13)
C150.4637 (4)0.5468 (4)0.0854 (3)0.0578 (16)
H150.40450.55510.04900.069*
C160.6210 (4)0.5546 (4)0.1741 (3)0.0440 (14)
C210.8340 (3)0.3625 (4)0.2837 (3)0.0382 (13)
C220.9169 (3)0.3941 (4)0.3312 (3)0.0503 (15)
H220.97140.38640.31690.060*
C230.7909 (3)0.4301 (4)0.3898 (3)0.0389 (13)
C240.8087 (3)0.3113 (4)0.2028 (3)0.0412 (14)
C250.8650 (4)0.2812 (4)0.1574 (3)0.0518 (15)
H250.92880.28840.17400.062*
C260.7012 (3)0.2497 (4)0.0923 (3)0.0400 (13)
C310.6186 (4)0.1145 (5)0.4751 (3)0.0502 (15)
C320.6054 (3)0.2126 (4)0.4535 (3)0.0430 (14)
C330.5913 (4)0.2761 (5)0.5137 (3)0.0571 (16)
H330.58230.34280.50150.068*
C340.5903 (4)0.2412 (6)0.5924 (4)0.077 (2)
H340.58170.28490.63280.093*
C350.6019 (5)0.1430 (7)0.6115 (5)0.088 (3)
H350.59990.12020.66420.105*
C360.6164 (4)0.0787 (5)0.5530 (4)0.0694 (19)
H360.62460.01200.56530.083*
C370.6130 (3)0.2545 (4)0.3705 (3)0.0381 (13)
C410.7178 (3)0.1665 (4)0.8473 (3)0.0381 (12)
C420.8047 (4)0.1558 (4)0.8383 (3)0.0485 (14)
C430.8544 (4)0.2328 (5)0.8205 (4)0.073 (2)
H430.91230.22190.81330.087*
C440.8183 (6)0.3257 (5)0.8131 (4)0.081 (2)
H440.85230.37880.80270.097*
C450.7319 (5)0.3402 (5)0.8213 (4)0.0709 (19)
H450.70620.40290.81500.085*
C460.6824 (4)0.2605 (4)0.8390 (3)0.0541 (15)
H460.62420.27110.84540.065*
C470.6591 (3)0.0811 (4)0.8611 (3)0.0382 (13)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni0.0287 (3)0.0303 (4)0.0332 (4)−0.0025 (3)0.0066 (3)−0.0019 (3)
N110.030 (2)0.033 (3)0.034 (2)−0.002 (2)0.0065 (18)−0.004 (2)
N120.050 (3)0.040 (3)0.073 (3)−0.010 (2)0.010 (2)0.002 (3)
N130.034 (2)0.032 (3)0.040 (2)−0.003 (2)0.0092 (19)0.003 (2)
N140.048 (3)0.039 (3)0.085 (4)−0.011 (2)0.010 (3)0.009 (3)
N210.032 (2)0.036 (3)0.032 (2)−0.005 (2)0.0042 (18)−0.005 (2)
N220.057 (3)0.061 (3)0.046 (3)−0.010 (3)0.010 (2)−0.021 (3)
N230.028 (2)0.036 (3)0.034 (2)−0.0033 (19)0.0062 (18)0.001 (2)
N240.045 (3)0.075 (4)0.033 (2)−0.007 (3)0.010 (2)−0.019 (2)
N310.074 (4)0.041 (3)0.056 (3)−0.008 (3)0.001 (3)0.010 (3)
N410.051 (4)0.086 (5)0.098 (5)−0.003 (3)0.031 (3)−0.015 (4)
O310.0360 (19)0.036 (2)0.044 (2)0.0023 (18)0.0133 (16)−0.0016 (19)
O320.036 (2)0.037 (2)0.044 (2)0.0014 (17)0.0126 (16)−0.0016 (18)
O330.097 (3)0.057 (3)0.068 (3)−0.015 (3)−0.010 (3)0.000 (3)
O340.090 (4)0.068 (3)0.106 (4)0.012 (3)0.010 (3)0.002 (3)
O410.117 (4)0.109 (4)0.188 (6)−0.018 (4)0.104 (4)−0.047 (4)
O420.142 (5)0.109 (5)0.133 (5)0.071 (4)0.071 (4)0.063 (4)
O430.100 (3)0.066 (3)0.054 (2)−0.041 (3)0.041 (2)−0.021 (2)
O440.049 (2)0.051 (2)0.036 (2)−0.0054 (19)0.0173 (17)0.0064 (19)
S110.0358 (8)0.0717 (12)0.0687 (10)−0.0177 (8)0.0004 (7)−0.0052 (9)
S120.0767 (12)0.0371 (9)0.0722 (11)0.0040 (8)0.0130 (9)0.0124 (9)
S210.0438 (9)0.0706 (12)0.0553 (9)−0.0171 (8)−0.0041 (7)−0.0125 (9)
S220.0544 (10)0.0708 (12)0.0624 (10)−0.0030 (9)0.0287 (8)−0.0206 (9)
C110.034 (3)0.044 (4)0.040 (3)−0.001 (3)0.009 (2)−0.001 (3)
C120.035 (3)0.064 (4)0.065 (4)−0.006 (3)−0.001 (3)0.001 (4)
C130.031 (3)0.044 (4)0.035 (3)−0.006 (3)0.005 (2)−0.006 (3)
C140.039 (3)0.042 (3)0.037 (3)0.005 (3)0.008 (2)0.005 (3)
C150.052 (4)0.052 (4)0.061 (4)0.011 (3)0.004 (3)0.014 (3)
C160.053 (4)0.033 (3)0.050 (3)−0.001 (3)0.022 (3)0.001 (3)
C210.029 (3)0.044 (3)0.039 (3)−0.007 (2)0.005 (2)0.003 (3)
C220.032 (3)0.061 (4)0.058 (4)−0.005 (3)0.012 (3)−0.005 (3)
C230.040 (3)0.039 (3)0.035 (3)−0.006 (3)0.007 (2)0.003 (3)
C240.032 (3)0.045 (4)0.049 (3)−0.002 (3)0.015 (3)−0.003 (3)
C250.044 (3)0.052 (4)0.059 (4)−0.001 (3)0.016 (3)−0.004 (3)
C260.042 (3)0.045 (4)0.033 (3)0.000 (3)0.011 (2)0.001 (3)
C310.049 (4)0.061 (4)0.037 (3)−0.011 (3)0.007 (3)0.003 (3)
C320.042 (3)0.049 (4)0.038 (3)−0.009 (3)0.012 (2)0.001 (3)
C330.064 (4)0.068 (5)0.044 (4)−0.002 (3)0.022 (3)−0.004 (3)
C340.078 (5)0.115 (7)0.048 (4)−0.019 (5)0.034 (4)−0.011 (5)
C350.084 (5)0.123 (8)0.054 (5)−0.029 (5)0.018 (4)0.022 (5)
C360.071 (4)0.074 (5)0.058 (4)−0.017 (4)0.010 (4)0.021 (4)
C370.030 (3)0.040 (4)0.042 (3)−0.003 (3)0.006 (2)−0.002 (3)
C410.043 (3)0.041 (3)0.031 (3)−0.009 (3)0.010 (2)−0.003 (3)
C420.041 (3)0.050 (4)0.057 (4)−0.012 (3)0.018 (3)−0.007 (3)
C430.063 (4)0.082 (5)0.083 (5)−0.037 (4)0.037 (4)−0.016 (5)
C440.116 (7)0.057 (5)0.087 (5)−0.037 (5)0.058 (5)−0.003 (4)
C450.103 (6)0.041 (4)0.069 (4)−0.005 (4)0.025 (4)0.005 (4)
C460.054 (4)0.042 (4)0.060 (4)−0.001 (3)0.008 (3)0.003 (3)
C470.035 (3)0.037 (3)0.040 (3)−0.007 (3)0.008 (3)−0.003 (3)
Geometric parameters (Å, °) top
Ni—N112.073 (4)S12—C151.707 (6)
Ni—N132.078 (4)S12—C161.726 (5)
Ni—N212.073 (4)S21—C221.716 (5)
Ni—N232.060 (4)S21—C231.731 (5)
Ni—O312.143 (3)S22—C251.723 (5)
Ni—O322.217 (3)S22—C261.732 (5)
Ni—C372.500 (5)C11—C121.332 (6)
N11—C131.314 (6)C11—C141.466 (7)
N11—C111.388 (6)C12—H120.9300
N12—C131.320 (6)C14—C151.335 (6)
N12—H12A0.7678C15—H150.9300
N12—H12B0.8257C21—C221.342 (6)
N13—C161.307 (6)C21—C241.453 (7)
N13—C141.396 (5)C22—H220.9300
N14—C161.353 (6)C24—C251.351 (6)
N14—H14A0.9484C25—H250.9300
N14—H14B0.8884C31—C321.379 (7)
N21—C231.320 (6)C31—C361.381 (7)
N21—C211.399 (6)C32—C331.378 (7)
N22—C231.332 (6)C32—C371.516 (7)
N22—H22A0.8674C33—C341.384 (7)
N22—H22B0.9161C33—H330.9300
N23—C261.327 (5)C34—C351.371 (9)
N23—C241.395 (5)C34—H340.9300
N24—C261.339 (6)C35—C361.365 (9)
N24—H24A0.8425C35—H350.9300
N24—H24B0.8409C36—H360.9300
N31—O331.220 (5)C41—C421.375 (7)
N31—O341.229 (6)C41—C461.377 (7)
N31—C311.468 (7)C41—C471.518 (7)
N41—O421.185 (6)C42—C431.370 (7)
N41—O411.228 (6)C43—C441.367 (9)
N41—C421.472 (8)C43—H430.9300
O31—C371.243 (5)C44—C451.369 (8)
O32—C371.267 (5)C44—H440.9300
O43—C471.240 (5)C45—C461.396 (7)
O44—C471.225 (5)C45—H450.9300
S11—C121.720 (6)C46—H460.9300
S11—C131.738 (5)
N23—Ni—N2180.04 (15)C14—C15—S12111.3 (4)
N23—Ni—N11101.07 (14)C14—C15—H15124.3
N21—Ni—N11178.41 (16)S12—C15—H15124.3
N23—Ni—N1398.01 (15)N13—C16—N14124.3 (5)
N21—Ni—N1398.64 (15)N13—C16—S12114.6 (4)
N11—Ni—N1380.09 (15)N14—C16—S12121.2 (4)
N23—Ni—O31157.03 (14)C22—C21—N21115.0 (5)
N21—Ni—O3189.64 (13)C22—C21—C24129.8 (5)
N11—Ni—O3189.73 (13)N21—C21—C24115.2 (4)
N13—Ni—O31103.83 (14)C21—C22—S21111.0 (4)
N23—Ni—O3298.57 (14)C21—C22—H22124.5
N21—Ni—O3287.37 (13)S21—C22—H22124.5
N11—Ni—O3293.59 (14)N21—C23—N22124.3 (5)
N13—Ni—O32163.11 (14)N21—C23—S21114.2 (4)
O31—Ni—O3260.22 (12)N22—C23—S21121.4 (4)
N23—Ni—C37128.30 (17)C25—C24—N23116.4 (5)
N21—Ni—C3787.41 (15)C25—C24—C21127.7 (5)
N11—Ni—C3792.77 (15)N23—C24—C21115.9 (4)
N13—Ni—C37133.54 (17)C24—C25—S22109.8 (4)
O31—Ni—C3729.82 (13)C24—C25—H25125.1
O32—Ni—C3730.42 (13)S22—C25—H25125.1
C13—N11—C11110.6 (4)N23—C26—N24124.8 (4)
C13—N11—Ni134.5 (3)N23—C26—S22114.5 (4)
C11—N11—Ni114.3 (3)N24—C26—S22120.7 (4)
C13—N12—H12A119.7C32—C31—C36122.7 (6)
C13—N12—H12B117.2C32—C31—N31121.9 (5)
H12A—N12—H12B114.3C36—C31—N31115.4 (6)
C16—N13—C14110.2 (4)C33—C32—C31117.4 (5)
C16—N13—Ni135.8 (4)C33—C32—C37118.8 (5)
C14—N13—Ni113.9 (3)C31—C32—C37123.6 (5)
C16—N14—H14A125.4C32—C33—C34120.4 (6)
C16—N14—H14B116.8C32—C33—H33119.8
H14A—N14—H14B113.0C34—C33—H33119.8
C23—N21—C21110.3 (4)C35—C34—C33120.9 (7)
C23—N21—Ni135.4 (3)C35—C34—H34119.5
C21—N21—Ni114.3 (3)C33—C34—H34119.5
C23—N22—H22A122.8C36—C35—C34119.7 (7)
C23—N22—H22B120.8C36—C35—H35120.1
H22A—N22—H22B116.3C34—C35—H35120.1
C26—N23—C24109.5 (4)C35—C36—C31118.9 (7)
C26—N23—Ni136.0 (3)C35—C36—H36120.6
C24—N23—Ni114.5 (3)C31—C36—H36120.6
C26—N24—H24A108.4O31—C37—O32121.3 (5)
C26—N24—H24B133.9O31—C37—C32118.2 (5)
H24A—N24—H24B117.5O32—C37—C32120.5 (5)
O33—N31—O34123.9 (6)O31—C37—Ni59.0 (3)
O33—N31—C31118.1 (5)O32—C37—Ni62.3 (2)
O34—N31—C31117.8 (5)C32—C37—Ni174.9 (4)
O42—N41—O41124.0 (7)C42—C41—C46116.4 (5)
O42—N41—C42119.3 (6)C42—C41—C47123.8 (5)
O41—N41—C42116.7 (7)C46—C41—C47119.7 (5)
C37—O31—Ni91.2 (3)C43—C42—C41123.1 (6)
C37—O32—Ni87.2 (3)C43—C42—N41118.6 (6)
C12—S11—C1389.0 (3)C41—C42—N41118.4 (5)
C15—S12—C1689.1 (3)C44—C43—C42119.6 (6)
C22—S21—C2389.4 (2)C44—C43—H43120.2
C25—S22—C2689.8 (3)C42—C43—H43120.2
C12—C11—N11115.5 (5)C43—C44—C45119.5 (6)
C12—C11—C14129.0 (5)C43—C44—H44120.2
N11—C11—C14115.5 (4)C45—C44—H44120.2
C11—C12—S11110.9 (4)C44—C45—C46119.8 (6)
C11—C12—H12124.5C44—C45—H45120.1
S11—C12—H12124.5C46—C45—H45120.1
N11—C13—N12124.8 (4)C41—C46—C45121.6 (6)
N11—C13—S11113.9 (4)C41—C46—H46119.2
N12—C13—S11121.3 (4)C45—C46—H46119.2
C15—C14—N13114.8 (5)O44—C47—O43126.1 (5)
C15—C14—C11129.5 (5)O44—C47—C41118.7 (5)
N13—C14—C11115.7 (4)O43—C47—C41115.1 (5)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N12—H12A···O43i0.772.012.779 (6)176
N12—H12B···O320.832.232.982 (6)151
N12—H12B···O330.832.482.999 (6)122
N14—H14A···O32ii0.952.062.953 (5)156
N14—H14B···N210.892.323.114 (6)149
N22—H22A···O310.872.202.886 (6)136
N22—H22B···O44iii0.922.062.923 (6)156
N24—H24A···N110.842.393.204 (5)161
N24—H24B···O44iv0.842.132.810 (5)137
Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x+3/2, y+1/2, −z+1/2; (iii) −x+3/2, y+1/2, −z+3/2; (iv) x, y, z−1.
Table 1
Selected geometric parameters (Å) top
Ni—N112.073 (4)Ni—N232.060 (4)
Ni—N132.078 (4)Ni—O312.143 (3)
Ni—N212.073 (4)Ni—O322.217 (3)
Table 2
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N12—H12A···O43i0.772.012.779 (6)176
N12—H12B···O320.832.232.982 (6)151
N12—H12B···O330.832.482.999 (6)122
N14—H14A···O32ii0.952.062.953 (5)156
N14—H14B···N210.892.323.114 (6)149
N22—H22A···O310.872.202.886 (6)136
N22—H22B···O44iii0.922.062.923 (6)156
N24—H24A···N110.842.393.204 (5)161
N24—H24B···O44iv0.842.132.810 (5)137
Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x+3/2, y+1/2, −z+1/2; (iii) −x+3/2, y+1/2, −z+3/2; (iv) x, y, z−1.
Acknowledgements top

The project was supported by the Educational Development Foundation of Shanghai Educational Committee, China, AB0448.

references
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