metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

Aqua(di­methylformamide){tris­[(1-methyl-1H-benzimidazol-2-yl)methyl]amine}nickel(II) dipicrate

aSchool of Chemical and Biological Engineering, Lanzhou Jiaotong University, Lanzhou 730070, People's Republic of China
*Correspondence e-mail: wuhuilu@163.com

(Received 11 July 2010; accepted 22 July 2010; online 31 July 2010)

In the title complex, [Ni(C27H27N7)(C3H7NO)(H2O)](C6H2N3O7)2, the NiII ion is coordinated in a slightly distorted octa­hedral coordination evironment by an NiN4O2 ligand set. The tris­(N-methyl­benzimidazol-2-ylmeth­yl)amine ligand is in a tetra­dentate mode while a coordinated water molecule and a dimethyl­formamide ligand complete the coordination. In the crystal structure, inter­molecular O—H⋯O hydrogen bonds link the cation and one of the pictrate anions into four-component centrosymmetric clusters.

Related literature

For the biological activity of compounds containing a benzimid­azole core, see: Horton et al. (2003[Horton, D. A., Bourne, G. T. & Smythe, M. L. (2003). Chem. Rev. 103, 893-930.]). For related structures, see Wu et al. (2005[Wu, H. L., Ying, W., Pen, L., Gao, Y. C. & Yu, K. B. (2005). Synth. React. Inorg. Met.-Org. Chem. 34, 553-558.], 2009[Wu, H. L., Huang, X. C., Yuan, J. K., Li, K., Ding, J., Yun, R. R., Dong, W. K. & Fan, X. Y. (2009). J. Coord. Chem. 62, 3446-3453.]).

[Scheme 1]

Experimental

Crystal data
  • [Ni(C27H27N7)(C3H7NO)(H2O)](C6H2N3O7)2

  • Mr = 1055.57

  • Triclinic, [P \overline 1]

  • a = 12.0768 (3) Å

  • b = 13.2619 (4) Å

  • c = 15.3544 (4) Å

  • α = 108.583 (1)°

  • β = 95.703 (1)°

  • γ = 99.506 (1)°

  • V = 2268.36 (11) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.52 mm−1

  • T = 153 K

  • 0.25 × 0.22 × 0.11 mm

Data collection
  • Bruker SMART APEXII diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS, University of Göttingen, Germany.]) Tmin = 0.882, Tmax = 0.945

  • 18738 measured reflections

  • 8420 independent reflections

  • 5743 reflections with I > 2σ(I)

  • Rint = 0.041

Refinement
  • R[F2 > 2σ(F2)] = 0.050

  • wR(F2) = 0.159

  • S = 1.18

  • 8420 reflections

  • 667 parameters

  • 2 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 1.01 e Å−3

  • Δρmin = −1.24 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O2—H2D⋯O3 0.86 (2) 1.86 (2) 2.708 (4) 169 (6)
O2—H2C⋯O3i 0.85 (2) 1.95 (3) 2.763 (4) 160 (7)
Symmetry code: (i) -x+1, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2000[Bruker (2000). APEX2 and SAINT. Bruker AXS Inc., Madison,Wisconsin, USA]); cell refinement: SAINT (Bruker, 2000[Bruker (2000). APEX2 and SAINT. Bruker AXS Inc., Madison,Wisconsin, USA]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

We are interested in tris(2-benzimidazolyl)alkanes and their derivatives and we have previously reported the crystal structure of some related complexes (Wu et al., 2009; Wu et al., 2005). The benzimidazole core is of a wide interest because of its diverse biological activities, and it is a well known structure in medicinal chemistry (Horton et al. 2003). The asymmetric unit of the title compound consists of an [Ni(Mentb)(DMF)(H2O)] cation (Mentb = tris(N-methylbenzimidazol-2-ylmethyl)amine and two picrate anions (Fig.1). The NiII ion is coordinated in a slightly- distorted octahedral coordination evironment by NiN4O2 ligand set. The Mentb ligand coordinates in a tetradentate mode while a coordinated water and a dimethylformamide ligand complete the coordination. In the crystal structure, intermolecular O-H···O hydrogen bonds link the cation and one of the pictrate anions into four component centrosymmetric clusters (Fig. 2).

Related literature top

For the biological activity of compounds containing a benzimidazole core, see: Horton et al. (2003). For related structures, see Wu et al. (2005, 2009).

Experimental top

To a stirred solution of tris(N-methylbenzimidazol-2-ylmethyl)amine (0.0899 g, 0.2 mmol) in hot MeOH (10 ml) was added Ni(C6H2N3O7)2 (0.0103 g, 0.2 mmol) in MeOH (5 ml). A pale green crystalline product formed rapidly. The precipitate was filtered off, washed with MeOH and absolute Et2O, and dried in vacuo. The dried precipitate was dissolved in DMF to form a pale green solution that was allowed to evaporate at room temperature. Green crystals suitable for X-ray diffraction studies were obtained after three weeks (Yield, 62%). Elemental analysis found: C, 47.79%; H, 3.82%; N, 18.58%; calcd. for C42 H40 N14 O16 Ni: C, 47.82%; H, 3.79%; N, 18.51%.

Refinement top

H atoms bonded to C atoms were placed in calculated positions and included in a riding-model approximation with C—H distances ranging from 0.95 to 0.99 Å and Uiso(H) = 1.2 Ueq(C) or Uiso(H) = 1.5 Ueq(Cmethyl). The water H atoms were located in a difference Fourier map and refined with the restraint O-H = 0.85 (2)Å.

Structure description top

We are interested in tris(2-benzimidazolyl)alkanes and their derivatives and we have previously reported the crystal structure of some related complexes (Wu et al., 2009; Wu et al., 2005). The benzimidazole core is of a wide interest because of its diverse biological activities, and it is a well known structure in medicinal chemistry (Horton et al. 2003). The asymmetric unit of the title compound consists of an [Ni(Mentb)(DMF)(H2O)] cation (Mentb = tris(N-methylbenzimidazol-2-ylmethyl)amine and two picrate anions (Fig.1). The NiII ion is coordinated in a slightly- distorted octahedral coordination evironment by NiN4O2 ligand set. The Mentb ligand coordinates in a tetradentate mode while a coordinated water and a dimethylformamide ligand complete the coordination. In the crystal structure, intermolecular O-H···O hydrogen bonds link the cation and one of the pictrate anions into four component centrosymmetric clusters (Fig. 2).

For the biological activity of compounds containing a benzimidazole core, see: Horton et al. (2003). For related structures, see Wu et al. (2005, 2009).

Computing details top

Data collection: APEX2 (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The asymmetric unit of the title compound. Hydrogen atoms have been omitted for clarity and the displacement ellipsoids are shown at the 30% probability level.
[Figure 2] Fig. 2. Part of the crystal structure of the title compound, showing hydrogen bonds as dashed lines. Only H atoms involved in hydrogen bonging are shown.
Aqua(dimethylformamide){tris[(1-methyl-1H-benzimidazol-2- yl)methyl]amine}nickel(II) dipicrate top
Crystal data top
[Ni(C27H27N7)(C3H7NO)(H2O)](C6H2N3O7)2Z = 2
Mr = 1055.57F(000) = 1092
Triclinic, P1Dx = 1.545 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 12.0768 (3) ÅCell parameters from 8420 reflections
b = 13.2619 (4) Åθ = 2.4–28.2°
c = 15.3544 (4) ŵ = 0.52 mm1
α = 108.583 (1)°T = 153 K
β = 95.703 (1)°Block, green
γ = 99.506 (1)°0.25 × 0.22 × 0.11 mm
V = 2268.36 (11) Å3
Data collection top
Bruker SMART APEXII
diffractometer
8420 independent reflections
Radiation source: fine-focus sealed tube5743 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.041
ω scansθmax = 25.5°, θmin = 3.1°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1414
Tmin = 0.882, Tmax = 0.945k = 1616
18738 measured reflectionsl = 1718
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.050H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.159 w = 1/[σ2(Fo2) + (0.0452P)2 + 5.4011P]
where P = (Fo2 + 2Fc2)/3
S = 1.18(Δ/σ)max = 0.001
8420 reflectionsΔρmax = 1.01 e Å3
667 parametersΔρmin = 1.24 e Å3
2 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0026 (5)
Crystal data top
[Ni(C27H27N7)(C3H7NO)(H2O)](C6H2N3O7)2γ = 99.506 (1)°
Mr = 1055.57V = 2268.36 (11) Å3
Triclinic, P1Z = 2
a = 12.0768 (3) ÅMo Kα radiation
b = 13.2619 (4) ŵ = 0.52 mm1
c = 15.3544 (4) ÅT = 153 K
α = 108.583 (1)°0.25 × 0.22 × 0.11 mm
β = 95.703 (1)°
Data collection top
Bruker SMART APEXII
diffractometer
8420 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
5743 reflections with I > 2σ(I)
Tmin = 0.882, Tmax = 0.945Rint = 0.041
18738 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0502 restraints
wR(F2) = 0.159H atoms treated by a mixture of independent and constrained refinement
S = 1.18Δρmax = 1.01 e Å3
8420 reflectionsΔρmin = 1.24 e Å3
667 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*/Ueq
Ni0.46074 (4)0.67214 (4)0.72572 (4)0.02153 (16)
O10.3577 (2)0.7136 (2)0.63281 (19)0.0281 (7)
O20.5213 (3)0.5564 (3)0.6231 (2)0.0274 (7)
O30.6467 (3)0.6084 (3)0.5008 (2)0.0476 (10)
O40.5367 (3)0.6964 (4)0.3971 (3)0.0792 (14)
O50.5862 (5)0.8686 (5)0.4310 (4)0.108 (2)
O60.9546 (4)1.0643 (3)0.5816 (3)0.0661 (13)
O71.0726 (4)0.9877 (4)0.6429 (3)0.0731 (14)
O80.9680 (4)0.6105 (4)0.5949 (4)0.0919 (17)
O90.7967 (4)0.5556 (4)0.6107 (4)0.0843 (15)
O100.2350 (3)0.3427 (3)0.9903 (2)0.0412 (8)
O110.3778 (3)0.5213 (3)0.9850 (2)0.0486 (10)
O120.2960 (3)0.6577 (4)1.0118 (3)0.0670 (12)
O130.0696 (3)0.6005 (3)0.8309 (3)0.0503 (9)
O140.1952 (3)0.4559 (3)0.8155 (2)0.0456 (9)
O150.0703 (4)0.2009 (4)0.9669 (3)0.0758 (14)
O160.0677 (4)0.1511 (3)0.8988 (4)0.0825 (16)
N10.6052 (3)0.7868 (3)0.7367 (2)0.0237 (7)
N20.7876 (3)0.8539 (3)0.7984 (2)0.0234 (8)
N30.3619 (3)0.5380 (3)0.7390 (2)0.0237 (8)
N40.3585 (3)0.3892 (3)0.7762 (2)0.0248 (8)
N50.4158 (3)0.7756 (3)0.8396 (2)0.0237 (8)
N60.4450 (3)0.8522 (3)0.9935 (2)0.0251 (8)
N70.5741 (3)0.6426 (3)0.8305 (2)0.0206 (7)
N80.2926 (3)0.7234 (3)0.4929 (2)0.0321 (9)
N90.6035 (4)0.7845 (5)0.4381 (3)0.0539 (13)
N100.9804 (4)0.9860 (4)0.5993 (3)0.0495 (12)
N110.8678 (4)0.6177 (4)0.5921 (3)0.0481 (11)
N120.2919 (3)0.5600 (4)0.9830 (3)0.0397 (10)
N130.0966 (3)0.5105 (3)0.8384 (3)0.0349 (9)
N140.0128 (4)0.2193 (4)0.9307 (3)0.0484 (12)
C10.6383 (3)0.8840 (3)0.7211 (3)0.0231 (9)
C20.5753 (4)0.9402 (3)0.6782 (3)0.0281 (10)
H2B0.49720.91190.65200.034*
C30.6314 (4)1.0377 (4)0.6758 (3)0.0357 (11)
H3A0.59111.07810.64770.043*
C40.7468 (4)1.0795 (4)0.7138 (4)0.0380 (11)
H4A0.78261.14720.71030.046*
C50.8102 (4)1.0252 (4)0.7563 (3)0.0339 (11)
H5A0.88831.05350.78220.041*
C60.7524 (3)0.9264 (3)0.7589 (3)0.0255 (9)
C70.6969 (3)0.7732 (3)0.7840 (3)0.0232 (9)
C80.6925 (3)0.6766 (3)0.8150 (3)0.0250 (9)
H8A0.71360.61630.76670.030*
H8B0.74680.69560.87330.030*
C90.5451 (3)0.5244 (3)0.8168 (3)0.0262 (9)
H9A0.56230.51270.87680.031*
H9B0.59030.48440.77270.031*
C100.4205 (3)0.4843 (3)0.7788 (3)0.0248 (9)
C110.2494 (3)0.3800 (3)0.7303 (3)0.0230 (9)
C120.1523 (4)0.2984 (4)0.7074 (3)0.0305 (10)
H12A0.15150.23370.72180.037*
C130.0562 (4)0.3171 (4)0.6622 (3)0.0318 (10)
H13A0.01270.26400.64530.038*
C140.0588 (4)0.4132 (4)0.6410 (3)0.0318 (10)
H14A0.00840.42320.61000.038*
C150.1555 (3)0.4924 (3)0.6637 (3)0.0265 (9)
H15A0.15650.55720.64960.032*
C160.2530 (3)0.4742 (3)0.7088 (3)0.0232 (9)
C170.5556 (4)0.7092 (4)0.9249 (3)0.0279 (10)
H17A0.52760.66010.95850.033*
H17B0.62910.75600.96100.033*
C180.4724 (3)0.7786 (3)0.9191 (3)0.0221 (9)
C190.3643 (3)0.8988 (3)0.9595 (3)0.0263 (9)
C200.3085 (4)0.9796 (4)1.0048 (3)0.0350 (11)
H20A0.32101.01171.07070.042*
C210.2339 (4)1.0103 (4)0.9487 (3)0.0344 (11)
H21A0.19471.06580.97650.041*
C220.2151 (4)0.9617 (4)0.8520 (3)0.0360 (11)
H22A0.16270.98450.81580.043*
C230.2704 (3)0.8811 (4)0.8072 (3)0.0313 (10)
H23A0.25690.84820.74130.038*
C240.3464 (3)0.8508 (3)0.8632 (3)0.0233 (9)
C250.9037 (4)0.8644 (4)0.8443 (3)0.0360 (11)
H25A0.90670.80290.86610.054*
H25B0.92530.93260.89750.054*
H25C0.95670.86480.79990.054*
C260.3955 (4)0.3098 (4)0.8132 (3)0.0334 (10)
H26A0.47580.33580.84190.050*
H26B0.38630.24020.76250.050*
H26C0.34940.29990.86000.050*
C270.4860 (4)0.8732 (4)1.0919 (3)0.0327 (10)
H27A0.54290.82971.09710.049*
H27B0.42210.85341.12200.049*
H27C0.52050.95061.12260.049*
C280.3449 (3)0.6785 (3)0.5465 (3)0.0247 (9)
H28A0.37400.61610.51720.030*
C290.2483 (7)0.8196 (6)0.5310 (4)0.088 (3)
H29A0.26210.84270.59920.132*
H29B0.16620.80370.50870.132*
H29C0.28620.87780.51120.132*
C300.2785 (4)0.6789 (4)0.3916 (3)0.0319 (10)
H30A0.31090.61360.37300.048*
H30B0.31770.73330.36820.048*
H30C0.19730.65980.36560.048*
C310.7227 (4)0.6930 (4)0.5180 (3)0.0322 (10)
C320.7101 (4)0.7865 (4)0.4924 (3)0.0310 (10)
C330.7918 (4)0.8803 (4)0.5177 (3)0.0354 (11)
H33A0.77750.94060.50100.042*
C340.8956 (4)0.8854 (4)0.5681 (3)0.0311 (10)
C350.9189 (4)0.7981 (4)0.5902 (3)0.0323 (10)
H35A0.99200.80140.62160.039*
C360.8360 (4)0.7063 (4)0.5667 (3)0.0302 (10)
C370.1626 (4)0.3812 (4)0.9551 (3)0.0298 (10)
C380.1809 (3)0.4884 (4)0.9463 (3)0.0313 (10)
C390.0991 (4)0.5297 (4)0.9091 (3)0.0294 (10)
H39A0.11700.60030.90480.035*
C400.0101 (3)0.4675 (4)0.8779 (3)0.0275 (10)
C410.0389 (4)0.3658 (4)0.8866 (3)0.0326 (11)
H41A0.11490.32500.86780.039*
C420.0447 (4)0.3260 (4)0.9229 (3)0.0291 (10)
H2D0.569 (4)0.575 (5)0.590 (4)0.07 (2)*
H2C0.479 (5)0.496 (3)0.590 (4)0.10 (3)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni0.0232 (3)0.0219 (3)0.0210 (3)0.0076 (2)0.0037 (2)0.0080 (2)
O10.0310 (15)0.0346 (17)0.0204 (15)0.0126 (13)0.0020 (12)0.0098 (13)
O20.0276 (16)0.0270 (17)0.0267 (16)0.0038 (14)0.0095 (14)0.0075 (14)
O30.054 (2)0.044 (2)0.0298 (18)0.0176 (18)0.0120 (16)0.0046 (16)
O40.042 (2)0.099 (4)0.079 (3)0.006 (3)0.011 (2)0.017 (3)
O50.125 (5)0.082 (4)0.100 (4)0.054 (4)0.051 (3)0.014 (3)
O60.102 (3)0.024 (2)0.072 (3)0.002 (2)0.042 (3)0.0137 (19)
O70.061 (3)0.074 (3)0.059 (3)0.031 (2)0.011 (2)0.018 (2)
O80.082 (3)0.098 (4)0.131 (5)0.051 (3)0.016 (3)0.070 (4)
O90.105 (4)0.055 (3)0.112 (4)0.008 (3)0.020 (3)0.058 (3)
O100.0372 (18)0.059 (2)0.0392 (19)0.0253 (17)0.0060 (15)0.0247 (17)
O110.0251 (17)0.081 (3)0.045 (2)0.0168 (18)0.0085 (15)0.025 (2)
O120.043 (2)0.049 (3)0.102 (4)0.0030 (19)0.006 (2)0.025 (2)
O130.051 (2)0.055 (2)0.059 (2)0.0289 (19)0.0080 (18)0.030 (2)
O140.0326 (18)0.056 (2)0.043 (2)0.0185 (17)0.0091 (15)0.0090 (17)
O150.099 (4)0.049 (3)0.073 (3)0.007 (3)0.019 (3)0.022 (2)
O160.064 (3)0.041 (2)0.135 (4)0.026 (2)0.011 (3)0.019 (3)
N10.0284 (18)0.0211 (18)0.0252 (18)0.0109 (15)0.0071 (15)0.0093 (15)
N20.0169 (16)0.0262 (19)0.0242 (18)0.0012 (14)0.0002 (14)0.0071 (15)
N30.0206 (16)0.0245 (19)0.0245 (18)0.0066 (14)0.0024 (14)0.0058 (15)
N40.0297 (18)0.0213 (18)0.0274 (19)0.0073 (15)0.0054 (15)0.0125 (15)
N50.0228 (17)0.0254 (19)0.0249 (18)0.0103 (15)0.0053 (14)0.0080 (15)
N60.0285 (18)0.0266 (19)0.0189 (17)0.0102 (15)0.0052 (14)0.0033 (15)
N70.0196 (16)0.0240 (18)0.0198 (17)0.0060 (14)0.0024 (13)0.0091 (14)
N80.040 (2)0.033 (2)0.0263 (19)0.0138 (18)0.0021 (16)0.0118 (17)
N90.051 (3)0.071 (4)0.035 (2)0.027 (3)0.004 (2)0.006 (2)
N100.067 (3)0.030 (2)0.042 (3)0.010 (2)0.019 (2)0.007 (2)
N110.065 (3)0.036 (3)0.051 (3)0.015 (2)0.011 (2)0.023 (2)
N120.032 (2)0.052 (3)0.041 (2)0.008 (2)0.0115 (18)0.022 (2)
N130.042 (2)0.043 (2)0.027 (2)0.025 (2)0.0044 (17)0.0135 (18)
N140.051 (3)0.035 (3)0.050 (3)0.011 (2)0.013 (2)0.007 (2)
C10.022 (2)0.020 (2)0.026 (2)0.0019 (17)0.0052 (17)0.0065 (17)
C20.035 (2)0.027 (2)0.026 (2)0.0087 (19)0.0065 (19)0.0117 (19)
C30.045 (3)0.030 (3)0.037 (3)0.013 (2)0.008 (2)0.015 (2)
C40.040 (3)0.025 (2)0.051 (3)0.001 (2)0.010 (2)0.019 (2)
C50.032 (2)0.028 (2)0.039 (3)0.004 (2)0.006 (2)0.008 (2)
C60.029 (2)0.024 (2)0.023 (2)0.0092 (18)0.0070 (18)0.0060 (18)
C70.030 (2)0.024 (2)0.021 (2)0.0123 (18)0.0068 (17)0.0095 (17)
C80.022 (2)0.031 (2)0.025 (2)0.0084 (18)0.0023 (17)0.0122 (18)
C90.028 (2)0.026 (2)0.032 (2)0.0118 (18)0.0046 (18)0.0161 (19)
C100.028 (2)0.024 (2)0.025 (2)0.0130 (18)0.0053 (17)0.0083 (18)
C110.028 (2)0.024 (2)0.021 (2)0.0064 (17)0.0108 (17)0.0094 (17)
C120.032 (2)0.025 (2)0.038 (3)0.0050 (19)0.013 (2)0.013 (2)
C130.029 (2)0.029 (2)0.040 (3)0.0050 (19)0.011 (2)0.014 (2)
C140.024 (2)0.036 (3)0.035 (2)0.0061 (19)0.0025 (19)0.012 (2)
C150.027 (2)0.023 (2)0.033 (2)0.0069 (18)0.0065 (18)0.0112 (19)
C160.029 (2)0.021 (2)0.023 (2)0.0065 (17)0.0099 (17)0.0100 (17)
C170.033 (2)0.033 (2)0.020 (2)0.0121 (19)0.0049 (18)0.0085 (18)
C180.024 (2)0.025 (2)0.021 (2)0.0069 (17)0.0024 (16)0.0121 (17)
C190.028 (2)0.024 (2)0.029 (2)0.0096 (18)0.0071 (18)0.0091 (18)
C200.036 (2)0.039 (3)0.028 (2)0.015 (2)0.010 (2)0.004 (2)
C210.037 (2)0.037 (3)0.034 (3)0.026 (2)0.009 (2)0.009 (2)
C220.031 (2)0.042 (3)0.039 (3)0.019 (2)0.007 (2)0.014 (2)
C230.026 (2)0.036 (3)0.028 (2)0.0089 (19)0.0006 (18)0.005 (2)
C240.0205 (19)0.024 (2)0.024 (2)0.0066 (17)0.0040 (16)0.0046 (17)
C250.030 (2)0.042 (3)0.036 (3)0.010 (2)0.001 (2)0.014 (2)
C260.039 (3)0.029 (2)0.037 (3)0.010 (2)0.006 (2)0.017 (2)
C270.042 (3)0.035 (3)0.017 (2)0.010 (2)0.0013 (19)0.0035 (19)
C280.027 (2)0.023 (2)0.029 (2)0.0078 (18)0.0027 (18)0.0147 (18)
C290.139 (7)0.097 (6)0.041 (3)0.098 (5)0.003 (4)0.010 (3)
C300.035 (2)0.042 (3)0.021 (2)0.004 (2)0.0017 (18)0.017 (2)
C310.036 (2)0.031 (3)0.027 (2)0.002 (2)0.017 (2)0.006 (2)
C320.032 (2)0.040 (3)0.024 (2)0.017 (2)0.0084 (18)0.010 (2)
C330.052 (3)0.033 (3)0.028 (2)0.014 (2)0.014 (2)0.015 (2)
C340.038 (2)0.021 (2)0.031 (2)0.0034 (19)0.011 (2)0.0076 (19)
C350.032 (2)0.034 (3)0.030 (2)0.006 (2)0.0072 (19)0.009 (2)
C360.042 (3)0.026 (2)0.029 (2)0.012 (2)0.011 (2)0.0151 (19)
C370.033 (2)0.040 (3)0.022 (2)0.021 (2)0.0073 (18)0.011 (2)
C380.024 (2)0.045 (3)0.027 (2)0.012 (2)0.0035 (18)0.013 (2)
C390.036 (2)0.035 (3)0.024 (2)0.015 (2)0.0112 (19)0.0133 (19)
C400.030 (2)0.036 (3)0.023 (2)0.020 (2)0.0046 (18)0.0118 (19)
C410.035 (2)0.034 (3)0.025 (2)0.015 (2)0.0026 (19)0.001 (2)
C420.035 (2)0.029 (2)0.029 (2)0.017 (2)0.0036 (19)0.0129 (19)
Geometric parameters (Å, º) top
Ni—N52.035 (3)C8—H8A0.9900
Ni—N32.052 (4)C8—H8B0.9900
Ni—O12.063 (3)C9—C101.500 (6)
Ni—N12.071 (3)C9—H9A0.9900
Ni—O22.106 (3)C9—H9B0.9900
Ni—N72.181 (3)C11—C161.384 (6)
O1—C281.240 (5)C11—C121.388 (6)
O2—H2D0.86 (2)C12—C131.391 (6)
O2—H2C0.85 (2)C12—H12A0.9500
O3—O30.000 (9)C13—C141.409 (6)
O3—C311.263 (5)C13—H13A0.9500
O4—N91.237 (6)C14—C151.366 (6)
O5—N91.204 (7)C14—H14A0.9500
O6—N101.232 (6)C15—C161.401 (6)
O7—N101.234 (6)C15—H15A0.9500
O8—N111.227 (6)C17—C181.485 (6)
O9—N111.209 (6)C17—H17A0.9900
O10—C371.244 (5)C17—H17B0.9900
O11—N121.233 (5)C19—C241.389 (6)
O12—N121.219 (6)C19—C201.394 (6)
O13—N131.230 (5)C20—C211.382 (6)
O14—N131.239 (5)C20—H20A0.9500
O15—N141.221 (6)C21—C221.395 (6)
O16—N141.216 (6)C21—H21A0.9500
N1—C71.333 (5)C22—C231.385 (6)
N1—C11.387 (5)C22—H22A0.9500
N2—C71.345 (5)C23—C241.390 (6)
N2—C61.388 (5)C23—H23A0.9500
N2—C251.470 (5)C25—H25A0.9800
N3—C101.318 (5)C25—H25B0.9800
N3—C161.387 (5)C25—H25C0.9800
N4—C101.343 (5)C26—H26A0.9800
N4—C111.399 (5)C26—H26B0.9800
N4—C261.455 (5)C26—H26C0.9800
N5—C181.324 (5)C27—H27A0.9800
N5—C241.390 (5)C27—H27B0.9800
N6—C181.355 (5)C27—H27C0.9800
N6—C191.381 (5)C28—H28A0.9500
N6—C271.465 (5)C29—H29A0.9800
N7—C91.490 (5)C29—H29B0.9800
N7—C81.493 (5)C29—H29C0.9800
N7—C171.498 (5)C30—H30A0.9800
N8—C281.329 (5)C30—H30B0.9800
N8—C291.438 (7)C30—H30C0.9800
N8—C301.457 (5)C31—O31.263 (5)
N9—C321.454 (6)C31—C321.441 (7)
N10—C341.450 (6)C31—C361.447 (6)
N11—C361.446 (6)C32—C331.372 (7)
N12—C381.450 (6)C33—C341.386 (7)
N13—C401.441 (5)C33—H33A0.9500
N14—C421.450 (6)C34—C351.369 (6)
C1—C61.388 (6)C35—C361.364 (6)
C1—C21.403 (6)C35—H35A0.9500
C2—C31.371 (6)C37—C421.446 (6)
C2—H2B0.9500C37—C381.454 (7)
C3—C41.403 (7)C38—C391.367 (6)
C3—H3A0.9500C39—C401.382 (6)
C4—C51.383 (7)C39—H39A0.9500
C4—H4A0.9500C40—C411.388 (7)
C5—C61.394 (6)C41—C421.363 (6)
C5—H5A0.9500C41—H41A0.9500
C7—C81.498 (6)
N5—Ni—N392.81 (14)C14—C13—H13A119.3
N5—Ni—O193.80 (12)C15—C14—C13121.8 (4)
N3—Ni—O1104.09 (12)C15—C14—H14A119.1
N5—Ni—N190.52 (13)C13—C14—H14A119.1
N3—Ni—N1158.76 (13)C14—C15—C16117.4 (4)
O1—Ni—N196.60 (13)C14—C15—H15A121.3
N5—Ni—O2170.87 (13)C16—C15—H15A121.3
N3—Ni—O284.00 (13)C11—C16—N3109.2 (4)
O1—Ni—O295.28 (12)C11—C16—C15120.5 (4)
N1—Ni—O289.44 (13)N3—C16—C15130.3 (4)
N5—Ni—N782.85 (13)C18—C17—N7112.0 (3)
N3—Ni—N779.47 (12)C18—C17—H17A109.2
O1—Ni—N7175.27 (12)N7—C17—H17A109.2
N1—Ni—N780.16 (13)C18—C17—H17B109.2
O2—Ni—N788.15 (12)N7—C17—H17B109.2
C28—O1—Ni128.2 (3)H17A—C17—H17B107.9
Ni—O2—H2D122 (4)N5—C18—N6111.8 (3)
Ni—O2—H2C121 (5)N5—C18—C17123.5 (4)
H2D—O2—H2C108 (6)N6—C18—C17124.7 (3)
O3—O3—C310 (10)N6—C19—C24106.3 (3)
C7—N1—C1105.8 (3)N6—C19—C20131.3 (4)
C7—N1—Ni112.8 (3)C24—C19—C20122.3 (4)
C1—N1—Ni140.8 (3)C21—C20—C19116.4 (4)
C7—N2—C6106.9 (3)C21—C20—H20A121.8
C7—N2—C25127.8 (4)C19—C20—H20A121.8
C6—N2—C25125.3 (4)C20—C21—C22121.4 (4)
C10—N3—C16105.7 (4)C20—C21—H21A119.3
C10—N3—Ni113.2 (3)C22—C21—H21A119.3
C16—N3—Ni140.4 (3)C23—C22—C21122.1 (4)
C10—N4—C11106.6 (3)C23—C22—H22A119.0
C10—N4—C26127.6 (3)C21—C22—H22A119.0
C11—N4—C26125.8 (3)C22—C23—C24116.8 (4)
C18—N5—C24106.2 (3)C22—C23—H23A121.6
C18—N5—Ni113.2 (3)C24—C23—H23A121.6
C24—N5—Ni140.6 (3)C19—C24—C23121.0 (4)
C18—N6—C19107.2 (3)C19—C24—N5108.5 (3)
C18—N6—C27126.9 (4)C23—C24—N5130.5 (4)
C19—N6—C27125.8 (3)N2—C25—H25A109.5
C9—N7—C8111.9 (3)N2—C25—H25B109.5
C9—N7—C17110.7 (3)H25A—C25—H25B109.5
C8—N7—C17111.3 (3)N2—C25—H25C109.5
C9—N7—Ni107.7 (2)H25A—C25—H25C109.5
C8—N7—Ni106.6 (2)H25B—C25—H25C109.5
C17—N7—Ni108.4 (2)N4—C26—H26A109.5
C28—N8—C29122.1 (4)N4—C26—H26B109.5
C28—N8—C30121.8 (4)H26A—C26—H26B109.5
C29—N8—C30116.0 (4)N4—C26—H26C109.5
O5—N9—O4122.3 (5)H26A—C26—H26C109.5
O5—N9—C32118.3 (5)H26B—C26—H26C109.5
O4—N9—C32119.3 (5)N6—C27—H27A109.5
O6—N10—O7124.6 (5)N6—C27—H27B109.5
O6—N10—C34117.6 (5)H27A—C27—H27B109.5
O7—N10—C34117.7 (5)N6—C27—H27C109.5
O9—N11—O8122.9 (5)H27A—C27—H27C109.5
O9—N11—C36119.7 (5)H27B—C27—H27C109.5
O8—N11—C36117.4 (5)O1—C28—N8123.7 (4)
O12—N12—O11122.3 (4)O1—C28—H28A118.2
O12—N12—C38117.8 (4)N8—C28—H28A118.2
O11—N12—C38119.9 (4)N8—C29—H29A109.5
O13—N13—O14123.1 (4)N8—C29—H29B109.5
O13—N13—C40118.5 (4)H29A—C29—H29B109.5
O14—N13—C40118.4 (4)N8—C29—H29C109.5
O16—N14—O15122.8 (5)H29A—C29—H29C109.5
O16—N14—C42118.8 (5)H29B—C29—H29C109.5
O15—N14—C42118.4 (5)N8—C30—H30A109.5
N1—C1—C6108.8 (4)N8—C30—H30B109.5
N1—C1—C2130.5 (4)H30A—C30—H30B109.5
C6—C1—C2120.8 (4)N8—C30—H30C109.5
C3—C2—C1117.0 (4)H30A—C30—H30C109.5
C3—C2—H2B121.5H30B—C30—H30C109.5
C1—C2—H2B121.5O3—C31—O30.0 (4)
C2—C3—C4121.7 (4)O3—C31—C32125.8 (4)
C2—C3—H3A119.1O3—C31—C32125.8 (4)
C4—C3—H3A119.1O3—C31—C36122.6 (4)
C5—C4—C3122.0 (4)O3—C31—C36122.6 (4)
C5—C4—H4A119.0C32—C31—C36111.6 (4)
C3—C4—H4A119.0C33—C32—C31124.4 (4)
C4—C5—C6115.9 (4)C33—C32—N9116.6 (5)
C4—C5—H5A122.0C31—C32—N9119.0 (4)
C6—C5—H5A122.0C32—C33—C34118.7 (4)
N2—C6—C1106.2 (4)C32—C33—H33A120.7
N2—C6—C5131.1 (4)C34—C33—H33A120.7
C1—C6—C5122.6 (4)C35—C34—C33121.4 (4)
N1—C7—N2112.3 (4)C35—C34—N10119.4 (4)
N1—C7—C8120.9 (4)C33—C34—N10119.1 (4)
N2—C7—C8126.8 (3)C36—C35—C34119.2 (4)
N7—C8—C7108.1 (3)C36—C35—H35A120.4
N7—C8—H8A110.1C34—C35—H35A120.4
C7—C8—H8A110.1C35—C36—N11115.7 (4)
N7—C8—H8B110.1C35—C36—C31124.5 (4)
C7—C8—H8B110.1N11—C36—C31119.8 (4)
H8A—C8—H8B108.4O10—C37—C42123.3 (4)
N7—C9—C10107.8 (3)O10—C37—C38125.8 (4)
N7—C9—H9A110.1C42—C37—C38110.7 (4)
C10—C9—H9A110.1C39—C38—N12116.6 (4)
N7—C9—H9B110.1C39—C38—C37124.7 (4)
C10—C9—H9B110.1N12—C38—C37118.7 (4)
H9A—C9—H9B108.5C38—C39—C40119.2 (4)
N3—C10—N4112.9 (4)C38—C39—H39A120.4
N3—C10—C9122.2 (4)C40—C39—H39A120.4
N4—C10—C9124.8 (4)C39—C40—C41121.3 (4)
C16—C11—C12123.0 (4)C39—C40—N13119.4 (4)
C16—C11—N4105.7 (3)C41—C40—N13119.3 (4)
C12—C11—N4131.3 (4)C42—C41—C40118.3 (4)
C11—C12—C13115.9 (4)C42—C41—H41A120.8
C11—C12—H12A122.0C40—C41—H41A120.8
C13—C12—H12A122.0C41—C42—C37125.8 (4)
C12—C13—C14121.4 (4)C41—C42—N14117.4 (4)
C12—C13—H13A119.3C37—C42—N14116.9 (4)
N5—Ni—O1—C28179.5 (3)C12—C11—C16—C151.4 (6)
N3—Ni—O1—C2886.7 (4)N4—C11—C16—C15178.5 (4)
N1—Ni—O1—C2888.5 (4)C10—N3—C16—C111.1 (5)
O2—Ni—O1—C281.6 (4)Ni—N3—C16—C11167.7 (3)
N7—Ni—O1—C28134.9 (14)C10—N3—C16—C15178.6 (4)
N5—Ni—N1—C794.7 (3)Ni—N3—C16—C1512.5 (7)
N3—Ni—N1—C74.4 (5)C14—C15—C16—C111.0 (6)
O1—Ni—N1—C7171.4 (3)C14—C15—C16—N3179.2 (4)
O2—Ni—N1—C776.2 (3)C9—N7—C17—C18121.2 (4)
N7—Ni—N1—C712.1 (3)C8—N7—C17—C18113.8 (4)
N5—Ni—N1—C174.3 (4)Ni—N7—C17—C183.2 (4)
N3—Ni—N1—C1173.4 (4)C24—N5—C18—N60.6 (5)
O1—Ni—N1—C119.6 (4)Ni—N5—C18—N6176.9 (3)
O2—Ni—N1—C1114.8 (4)C24—N5—C18—C17179.4 (4)
N7—Ni—N1—C1156.9 (5)Ni—N5—C18—C173.1 (5)
N5—Ni—N3—C10100.0 (3)C19—N6—C18—N50.7 (5)
O1—Ni—N3—C10165.4 (3)C27—N6—C18—N5176.5 (4)
N1—Ni—N3—C101.3 (6)C19—N6—C18—C17179.3 (4)
O2—Ni—N3—C1071.4 (3)C27—N6—C18—C173.6 (7)
N7—Ni—N3—C1017.8 (3)N7—C17—C18—N54.4 (6)
N5—Ni—N3—C1691.7 (4)N7—C17—C18—N6175.5 (4)
O1—Ni—N3—C162.9 (4)C18—N6—C19—C240.5 (5)
N1—Ni—N3—C16169.6 (4)C27—N6—C19—C24176.3 (4)
O2—Ni—N3—C1696.9 (4)C18—N6—C19—C20178.9 (5)
N7—Ni—N3—C16173.9 (4)C27—N6—C19—C205.2 (8)
N3—Ni—N5—C1879.7 (3)N6—C19—C20—C21177.9 (5)
O1—Ni—N5—C18175.9 (3)C24—C19—C20—C210.3 (7)
N1—Ni—N5—C1879.3 (3)C19—C20—C21—C220.8 (7)
O2—Ni—N5—C1810.5 (10)C20—C21—C22—C230.6 (8)
N7—Ni—N5—C180.7 (3)C21—C22—C23—C240.2 (7)
N3—Ni—N5—C24104.1 (4)N6—C19—C24—C23179.1 (4)
O1—Ni—N5—C240.2 (4)C20—C19—C24—C230.5 (7)
N1—Ni—N5—C2496.9 (4)N6—C19—C24—N50.1 (5)
O2—Ni—N5—C24173.4 (7)C20—C19—C24—N5178.8 (4)
N7—Ni—N5—C24176.9 (4)C22—C23—C24—C190.7 (7)
N5—Ni—N7—C9121.3 (3)C22—C23—C24—N5178.3 (4)
N3—Ni—N7—C927.1 (2)C18—N5—C24—C190.3 (5)
O1—Ni—N7—C9166.3 (14)Ni—N5—C24—C19176.0 (3)
N1—Ni—N7—C9146.9 (3)C18—N5—C24—C23179.4 (5)
O2—Ni—N7—C957.1 (3)Ni—N5—C24—C233.1 (8)
N5—Ni—N7—C8118.4 (3)Ni—O1—C28—N8167.6 (3)
N3—Ni—N7—C8147.3 (3)C29—N8—C28—O11.6 (8)
O1—Ni—N7—C873.5 (15)C30—N8—C28—O1179.4 (4)
N1—Ni—N7—C826.6 (2)O3—O3—C31—C320.00 (4)
O2—Ni—N7—C863.1 (2)O3—O3—C31—C360.00 (17)
N5—Ni—N7—C171.5 (3)O3—C31—C32—C33175.3 (4)
N3—Ni—N7—C1792.8 (3)O3—C31—C32—C33175.3 (4)
O1—Ni—N7—C1746.4 (16)C36—C31—C32—C335.2 (6)
N1—Ni—N7—C1793.2 (3)O3—C31—C32—N93.0 (7)
O2—Ni—N7—C17177.0 (3)O3—C31—C32—N93.0 (7)
C7—N1—C1—C61.1 (4)C36—C31—C32—N9176.5 (4)
Ni—N1—C1—C6170.6 (3)O5—N9—C32—C3311.2 (7)
C7—N1—C1—C2177.1 (4)O4—N9—C32—C33165.0 (5)
Ni—N1—C1—C27.6 (8)O5—N9—C32—C31167.2 (5)
N1—C1—C2—C3177.8 (4)O4—N9—C32—C3116.6 (7)
C6—C1—C2—C30.2 (6)C31—C32—C33—C342.7 (7)
C1—C2—C3—C40.4 (7)N9—C32—C33—C34178.9 (4)
C2—C3—C4—C50.5 (8)C32—C33—C34—C352.1 (7)
C3—C4—C5—C60.2 (7)C32—C33—C34—N10176.9 (4)
C7—N2—C6—C10.2 (4)O6—N10—C34—C35176.9 (4)
C25—N2—C6—C1178.2 (4)O7—N10—C34—C352.0 (7)
C7—N2—C6—C5177.5 (4)O6—N10—C34—C332.1 (7)
C25—N2—C6—C54.1 (7)O7—N10—C34—C33179.0 (4)
N1—C1—C6—N20.6 (5)C33—C34—C35—C363.8 (7)
C2—C1—C6—N2177.8 (4)N10—C34—C35—C36175.2 (4)
N1—C1—C6—C5178.5 (4)C34—C35—C36—N11179.7 (4)
C2—C1—C6—C50.1 (6)C34—C35—C36—C310.7 (7)
C4—C5—C6—N2177.2 (4)O9—N11—C36—C35149.3 (5)
C4—C5—C6—C10.1 (7)O8—N11—C36—C3529.7 (7)
C1—N1—C7—N21.3 (5)O9—N11—C36—C3131.7 (7)
Ni—N1—C7—N2174.1 (3)O8—N11—C36—C31149.3 (5)
C1—N1—C7—C8178.9 (4)O3—C31—C36—C35177.0 (4)
Ni—N1—C7—C86.1 (5)O3—C31—C36—C35177.0 (4)
C6—N2—C7—N11.0 (5)C32—C31—C36—C353.5 (6)
C25—N2—C7—N1177.4 (4)O3—C31—C36—N114.1 (7)
C6—N2—C7—C8179.3 (4)O3—C31—C36—N114.1 (7)
C25—N2—C7—C82.4 (7)C32—C31—C36—N11175.4 (4)
C9—N7—C8—C7152.8 (3)O12—N12—C38—C3927.7 (6)
C17—N7—C8—C782.8 (4)O11—N12—C38—C39152.9 (4)
Ni—N7—C8—C735.2 (4)O12—N12—C38—C37149.4 (5)
N1—C7—C8—N729.5 (5)O11—N12—C38—C3729.9 (6)
N2—C7—C8—N7150.7 (4)O10—C37—C38—C39178.5 (4)
C8—N7—C9—C10147.5 (3)C42—C37—C38—C392.4 (6)
C17—N7—C9—C1087.8 (4)O10—C37—C38—N121.6 (7)
Ni—N7—C9—C1030.6 (4)C42—C37—C38—N12174.5 (4)
C16—N3—C10—N40.6 (5)N12—C38—C39—C40176.3 (4)
Ni—N3—C10—N4171.7 (3)C37—C38—C39—C400.7 (7)
C16—N3—C10—C9177.0 (4)C38—C39—C40—C412.3 (6)
Ni—N3—C10—C94.7 (5)C38—C39—C40—N13179.8 (4)
C11—N4—C10—N30.2 (5)O13—N13—C40—C392.2 (6)
C26—N4—C10—N3180.0 (4)O14—N13—C40—C39176.2 (4)
C11—N4—C10—C9176.2 (4)O13—N13—C40—C41179.8 (4)
C26—N4—C10—C93.7 (7)O14—N13—C40—C411.8 (6)
N7—C9—C10—N319.0 (5)C39—C40—C41—C423.0 (6)
N7—C9—C10—N4165.0 (4)N13—C40—C41—C42179.0 (4)
C10—N4—C11—C160.9 (4)C40—C41—C42—C371.0 (7)
C26—N4—C11—C16179.3 (4)C40—C41—C42—N14179.6 (4)
C10—N4—C11—C12179.2 (4)O10—C37—C42—C41177.8 (4)
C26—N4—C11—C120.6 (7)C38—C37—C42—C411.6 (6)
C16—C11—C12—C131.0 (6)O10—C37—C42—N141.6 (7)
N4—C11—C12—C13178.9 (4)C38—C37—C42—N14177.8 (4)
C11—C12—C13—C140.3 (7)O16—N14—C42—C41128.6 (5)
C12—C13—C14—C150.1 (7)O15—N14—C42—C4149.3 (6)
C13—C14—C15—C160.4 (7)O16—N14—C42—C3751.9 (6)
C12—C11—C16—N3178.8 (4)O15—N14—C42—C37130.2 (5)
N4—C11—C16—N31.3 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2D···O30.86 (2)1.86 (2)2.708 (4)169 (6)
O2—H2C···O3i0.85 (2)1.95 (3)2.763 (4)160 (7)
Symmetry code: (i) x+1, y+1, z+1.

Experimental details

Crystal data
Chemical formula[Ni(C27H27N7)(C3H7NO)(H2O)](C6H2N3O7)2
Mr1055.57
Crystal system, space groupTriclinic, P1
Temperature (K)153
a, b, c (Å)12.0768 (3), 13.2619 (4), 15.3544 (4)
α, β, γ (°)108.583 (1), 95.703 (1), 99.506 (1)
V3)2268.36 (11)
Z2
Radiation typeMo Kα
µ (mm1)0.52
Crystal size (mm)0.25 × 0.22 × 0.11
Data collection
DiffractometerBruker SMART APEXII
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.882, 0.945
No. of measured, independent and
observed [I > 2σ(I)] reflections
18738, 8420, 5743
Rint0.041
(sin θ/λ)max1)0.606
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.050, 0.159, 1.18
No. of reflections8420
No. of parameters667
No. of restraints2
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)1.01, 1.24

Computer programs: APEX2 (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2D···O30.86 (2)1.86 (2)2.708 (4)169 (6)
O2—H2C···O3i0.85 (2)1.95 (3)2.763 (4)160 (7)
Symmetry code: (i) x+1, y+1, z+1.
 

Acknowledgements

We are grateful for financially support and a grant from the `Qing Lan' Talent Engineering Funds and Students' Science and Technology Innovation Funds (grant No. DXS2008–040,041) of Lanzhou Jiaotong University. A grant from the Middle-Young Age Science Foundation (grant No. 3YS061-A25–023) and the `Long Yuan Qing Nian' of Gansu Province is also acknowledged

References

First citationBruker (2000). APEX2 and SAINT. Bruker AXS Inc., Madison,Wisconsin, USA  Google Scholar
First citationHorton, D. A., Bourne, G. T. & Smythe, M. L. (2003). Chem. Rev. 103, 893–930.  Web of Science CrossRef PubMed CAS Google Scholar
First citationSheldrick, G. M. (1996). SADABS, University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationWu, H. L., Huang, X. C., Yuan, J. K., Li, K., Ding, J., Yun, R. R., Dong, W. K. & Fan, X. Y. (2009). J. Coord. Chem. 62, 3446–3453.  Web of Science CrossRef CAS Google Scholar
First citationWu, H. L., Ying, W., Pen, L., Gao, Y. C. & Yu, K. B. (2005). Synth. React. Inorg. Met.-Org. Chem. 34, 553–558.  Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds