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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 65| Part 12| December 2009| Pages m1526-m1527

Di­aqua­bis­(N,N′-di­benzyl­ethane-1,2-di­amine-κ2N,N′)nickel(II) dichloride N,N-di­methyl­formamide solvate

aDepartment of Chemical Engineering, Huaihai Institute of Technology, Lianyungang, Jiangsu 222005, People's Republic of China, and bCollege of Chemistry and Chemical Engineering, Liaocheng University, Shandong 252059, People's Republic of China
*Correspondence e-mail: liu222005@hhit.edu.cn

(Received 16 October 2009; accepted 2 November 2009; online 7 November 2009)

The asymmetric unit of the title complex, [Ni(C16H20N2)2(H2O)2]Cl2·C3H7NO, consists of two NiII atoms, each lying on an inversion center, two Cl anions, two N,N′-dibenzyl­ethane-1,2-diamine ligands, two coordinated water mol­ecules and one N,N-dimethyl­formamide solvent mol­ecule. Each NiII atom is six-coordinated in a distorted octa­hedral coordination geometry, with the equatorial plane formed by four N atoms and the axial positions occupied by two water mol­ecules. The complex mol­ecules are linked into a chain along [001] by N—H⋯Cl, N—H⋯O and O—H⋯Cl hydrogen bonds. The C atoms and H atoms of the solvent mol­ecule are disordered over two sites in a ratio of 0.52 (2):0.48 (2).

Related literature

For related structures, see: Xia et al. (2007a[Xia, H.-T., Liu, Y.-F., Wang, D.-Q. & Yang, S.-P. (2007a). Acta Cryst. E63, m1162-m1164.],b[Xia, H.-T., Liu, Y.-F., Wang, D.-Q. & Yang, S.-P. (2007b). Acta Cryst. E63, m2512-m2513.]).

[Scheme 1]

Experimental

Crystal data
  • [Ni(C16H20N2)2(H2O)2]Cl2·C3H7NO

  • Mr = 719.42

  • Triclinic, [P \overline 1]

  • a = 11.898 (1) Å

  • b = 12.588 (1) Å

  • c = 14.872 (2) Å

  • α = 104.769 (2)°

  • β = 95.368 (1)°

  • γ = 111.399 (2)°

  • V = 1961.8 (3) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.67 mm−1

  • T = 298 K

  • 0.42 × 0.40 × 0.35 mm

Data collection
  • Siemens SMART 1000 CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.767, Tmax = 0.800

  • 10138 measured reflections

  • 6781 independent reflections

  • 4690 reflections with I > 2σ(I)

  • Rint = 0.018

Refinement
  • R[F2 > 2σ(F2)] = 0.066

  • wR(F2) = 0.201

  • S = 1.02

  • 6781 reflections

  • 450 parameters

  • H-atom parameters constrained

  • Δρmax = 1.15 e Å−3

  • Δρmin = −0.75 e Å−3

Table 1
Selected bond lengths (Å)

Ni1—O1 2.100 (3)
Ni1—N1 2.131 (4)
Ni1—N2 2.143 (4)
Ni2—O2 2.111 (3)
Ni2—N3 2.140 (4)
Ni2—N4 2.130 (4)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O1—H1C⋯Cl2 0.85 2.26 3.055 (4) 155
O1—H1D⋯Cl1i 0.85 2.24 3.078 (4) 169
O2—H2C⋯Cl1i 0.85 2.24 3.071 (4) 168
O2—H2D⋯Cl2 0.85 2.19 3.041 (4) 174
N1—H1⋯Cl1ii 0.91 2.54 3.444 (4) 171
N2—H2⋯O3iii 0.91 2.20 3.102 (8) 169
N3—H3⋯Cl1 0.91 2.55 3.400 (4) 155
N4—H4⋯Cl2i 0.91 2.54 3.428 (5) 167
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) x, y, z+1; (iii) -x+1, -y+1, -z+2.

Data collection: SMART (Siemens, 1996[Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Siemens, 1996[Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments 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.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

We have reported the crystal structures of nickel complexes with diamine derivatives (Xia et al., 2007a, b). As a further study of the structures of such complexes, we reported here the crystal structure of the title complex.

The NiII atom has a slightly distorted octahedral configuration, coordinated by four N atoms from two N,N'-dibenzylethane-1,2-diamine ligands and two O atoms of two water molecules (Fig. 1 and Table 1). The four N atoms occupy the equatorial positions and O atoms occupy the axial positions. The complex molecules are linked into a chain along the [0 0 1] direction by N—H···Cl and O—H···Cl hydrogen bonds (Table 2). The disordered N,N-dimethylformamide (DMF) solvent molecule is attached to the complex molecule through an N—H···O hydrogen bond.

Related literature top

For related structures, see: Xia et al. (2007a,b).

Experimental top

A solution of N,N'-dibenzylethane-1,2-diamine (1 mmol) in ethanol (20 ml) and a solution of nickel(II) chloride (1 mmol) in ethanol (10 ml) was mixed and the reaction mixture was stirred for 4 h at 328 K. The solution was then cooled slowly to room temperature and filtered. Blue crystals suitable for X-ray diffraction were obtained by evaporation of the ethanol solution.

Refinement top

H atoms were located in difference Fourier maps and refined as riding atoms, with C—H = 0.93 (aryl, formyl), 0.97 (methylene) and 0.96 Å (methyl), N—H = 0.91 Å and O—H = 0.85 Å and with Uiso(H) = 1.2(1.5 for methyl)Ueq(C,N,O). The C and H atoms in the DMF molecule were found to be disordered over two site. The occupancy factors of the two sites were refined to 0.52 (2) and 0.48 (2). The highest residual electron density was found 0.06 Å from C27 and the deepest hole 0.17 Å from C29.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); 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 of the title compound. Displacement ellipsoids are drawn at the 30% probability level. [Symmetry codes: (i) 1-x, 1-y, 2-z; (ii) 1-x, 1-y, 1-z.]
Diaquabis(N,N'-dibenzylethane-1,2-diamine- κ2N,N')nickel(II) dichloride N,N-dimethylformamide solvate top
Crystal data top
[Ni(C16H20N2)2(H2O)2]Cl2·C3H7NOZ = 2
Mr = 719.42F(000) = 764
Triclinic, P1Dx = 1.218 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 11.898 (1) ÅCell parameters from 3426 reflections
b = 12.588 (1) Åθ = 2.4–28.9°
c = 14.872 (2) ŵ = 0.67 mm1
α = 104.769 (2)°T = 298 K
β = 95.368 (1)°Block, blue
γ = 111.399 (2)°0.42 × 0.40 × 0.35 mm
V = 1961.8 (3) Å3
Data collection top
Siemens SMART 1000 CCD
diffractometer
6781 independent reflections
Radiation source: fine-focus sealed tube4690 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.018
ϕ and ω scansθmax = 25.0°, θmin = 1.5°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1412
Tmin = 0.767, Tmax = 0.800k = 1414
10138 measured reflectionsl = 1517
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)] = 0.066Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.201H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0878P)2 + 5.0932P]
where P = (Fo2 + 2Fc2)/3
6781 reflections(Δ/σ)max = 0.001
450 parametersΔρmax = 1.15 e Å3
0 restraintsΔρmin = 0.75 e Å3
Crystal data top
[Ni(C16H20N2)2(H2O)2]Cl2·C3H7NOγ = 111.399 (2)°
Mr = 719.42V = 1961.8 (3) Å3
Triclinic, P1Z = 2
a = 11.898 (1) ÅMo Kα radiation
b = 12.588 (1) ŵ = 0.67 mm1
c = 14.872 (2) ÅT = 298 K
α = 104.769 (2)°0.42 × 0.40 × 0.35 mm
β = 95.368 (1)°
Data collection top
Siemens SMART 1000 CCD
diffractometer
6781 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
4690 reflections with I > 2σ(I)
Tmin = 0.767, Tmax = 0.800Rint = 0.018
10138 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0660 restraints
wR(F2) = 0.201H-atom parameters constrained
S = 1.02Δρmax = 1.15 e Å3
6781 reflectionsΔρmin = 0.75 e Å3
450 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Ni10.50000.50001.00000.0360 (2)
Ni20.50000.50000.50000.0373 (2)
Cl10.61243 (14)0.70108 (13)0.30429 (9)0.0584 (4)
Cl20.68699 (16)0.69555 (13)0.79097 (10)0.0709 (5)
N10.6479 (4)0.6692 (4)1.0730 (3)0.0487 (10)
H10.64810.68221.13610.058*
N20.4030 (4)0.6078 (4)0.9772 (3)0.0523 (11)
H20.33010.57890.99590.063*
N30.6784 (4)0.5756 (4)0.4682 (3)0.0459 (10)
H30.67630.63110.43980.055*
N40.4979 (4)0.3356 (4)0.4135 (3)0.0465 (10)
H40.45400.31800.35430.056*
N50.8816 (7)0.4000 (8)0.7989 (6)0.113 (2)
O10.5688 (3)0.4934 (3)0.8746 (2)0.0506 (9)
H1C0.59800.56260.86760.061*
H1D0.51270.44520.82630.061*
O20.5814 (3)0.4709 (3)0.6187 (2)0.0479 (8)
H2C0.52550.41510.63150.057*
H2D0.60570.53400.66630.057*
O30.8337 (6)0.4541 (7)0.9394 (5)0.118 (2)
C10.6111 (6)0.7603 (5)1.0454 (4)0.0594 (15)
H1A0.62660.76200.98280.071*
H1B0.65940.83951.09040.071*
C20.4762 (6)0.7274 (5)1.0450 (4)0.0616 (15)
H2A0.46140.72811.10810.074*
H2B0.45140.78601.02740.074*
C30.7735 (6)0.6875 (6)1.0621 (5)0.0678 (17)
H3A0.77540.67080.99500.081*
H3B0.79510.62971.08390.081*
C40.8705 (5)0.8117 (5)1.1149 (4)0.0595 (15)
C50.9575 (6)0.8730 (6)1.0714 (5)0.079 (2)
H50.95580.83751.00790.095*
C61.0475 (7)0.9859 (7)1.1193 (6)0.091 (2)
H61.10641.02471.08840.109*
C71.0504 (7)1.0406 (7)1.2117 (6)0.084 (2)
H71.10981.11761.24330.101*
C80.9665 (6)0.9831 (6)1.2580 (5)0.0779 (19)
H80.96811.01981.32120.093*
C90.8785 (6)0.8689 (6)1.2093 (5)0.0721 (18)
H90.82250.82891.24150.087*
C100.3726 (6)0.6090 (6)0.8795 (4)0.0608 (15)
H10A0.31910.52790.84020.073*
H10B0.44820.63230.85560.073*
C110.3108 (7)0.6912 (7)0.8681 (5)0.0738 (18)
C120.3740 (8)0.7947 (7)0.8463 (5)0.087 (2)
H120.45420.81040.83760.105*
C130.3246 (10)0.8759 (8)0.8368 (6)0.105 (3)
H130.36900.94440.82150.127*
C140.2083 (11)0.8505 (9)0.8508 (7)0.111 (3)
H140.17360.90480.84660.134*
C150.1388 (10)0.7483 (10)0.8709 (7)0.114 (3)
H150.05790.73260.87760.137*
C160.1923 (8)0.6681 (8)0.8810 (6)0.093 (2)
H160.14770.59980.89640.111*
C170.6887 (6)0.4775 (6)0.3940 (5)0.0690 (17)
H17A0.65320.47580.33200.083*
H17B0.77520.49350.39590.083*
C180.6255 (6)0.3591 (6)0.4070 (5)0.0700 (18)
H18A0.62770.29690.35380.084*
H18B0.66870.35650.46450.084*
C190.7840 (6)0.6380 (6)0.5480 (4)0.0681 (17)
H19A0.79540.57860.57420.082*
H19B0.76320.69100.59690.082*
C200.9051 (5)0.7107 (6)0.5289 (4)0.0619 (15)
C210.9161 (6)0.7821 (7)0.4713 (5)0.0765 (19)
H210.84500.78240.43970.092*
C221.0293 (7)0.8535 (7)0.4590 (6)0.088 (2)
H221.03330.90060.41930.105*
C231.1351 (7)0.8556 (8)0.5043 (6)0.094 (2)
H231.21130.90200.49450.113*
C241.1279 (7)0.7882 (8)0.5646 (6)0.095 (2)
H241.19940.79090.59810.115*
C251.0129 (6)0.7157 (7)0.5754 (5)0.082 (2)
H251.00900.66920.61560.098*
C260.4477 (7)0.2302 (5)0.4460 (5)0.0692 (17)
H26A0.36520.21950.45550.083*
H26B0.49790.24690.50730.083*
C270.4410 (9)0.1149 (6)0.3818 (6)0.088 (2)
C280.3607 (10)0.0594 (7)0.2950 (7)0.109 (3)
H280.31290.09560.27340.131*
C290.3520 (11)0.0524 (8)0.2396 (7)0.119 (3)
H290.29560.09350.18200.142*
C300.4289 (10)0.1003 (8)0.2721 (7)0.108 (3)
H300.42330.17430.23470.130*
C310.5115 (10)0.0458 (8)0.3553 (7)0.108 (3)
H310.56330.07930.37520.130*
C320.5149 (9)0.0617 (7)0.4086 (6)0.102 (3)
H320.57070.10110.46660.122*
C330.8308 (18)0.4586 (19)0.8564 (15)0.111 (8)0.52 (2)
H330.79300.50320.83510.133*0.52 (2)
C340.945 (3)0.326 (3)0.814 (2)0.125 (8)0.52 (2)
H34A0.96470.33770.88130.187*0.52 (2)
H34B1.01980.34800.79070.187*0.52 (2)
H34C0.89300.24310.78190.187*0.52 (2)
C350.877 (2)0.425 (2)0.7071 (17)0.137 (9)0.52 (2)
H35A0.80740.36130.66120.206*0.52 (2)
H35B0.95130.43040.68530.206*0.52 (2)
H35C0.86800.49960.71530.206*0.52 (2)
C33'0.8850 (18)0.400 (2)0.8893 (16)0.109 (8)0.48 (2)
H33'0.92580.36050.91400.130*0.48 (2)
C34'0.803 (2)0.441 (2)0.7512 (16)0.119 (8)0.48 (2)
H34D0.72660.42070.77220.178*0.48 (2)
H34E0.78800.40380.68380.178*0.48 (2)
H34F0.84310.52680.76560.178*0.48 (2)
C35'0.946 (3)0.329 (3)0.751 (2)0.128 (9)0.48 (2)
H35D1.02490.35250.79030.193*0.48 (2)
H35E0.95590.34170.69120.193*0.48 (2)
H35F0.89740.24500.74110.193*0.48 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.0397 (5)0.0367 (5)0.0311 (4)0.0144 (4)0.0077 (3)0.0110 (4)
Ni20.0429 (5)0.0381 (5)0.0319 (4)0.0171 (4)0.0097 (4)0.0107 (4)
Cl10.0708 (9)0.0528 (8)0.0422 (7)0.0125 (7)0.0107 (6)0.0183 (6)
Cl20.0868 (11)0.0541 (9)0.0448 (8)0.0003 (8)0.0074 (7)0.0159 (6)
N10.050 (3)0.047 (3)0.047 (2)0.016 (2)0.013 (2)0.013 (2)
N20.059 (3)0.055 (3)0.051 (3)0.030 (2)0.012 (2)0.021 (2)
N30.046 (2)0.051 (3)0.048 (2)0.023 (2)0.015 (2)0.020 (2)
N40.054 (3)0.044 (2)0.044 (2)0.023 (2)0.015 (2)0.0112 (19)
N50.109 (6)0.158 (8)0.100 (6)0.083 (6)0.037 (5)0.038 (5)
O10.058 (2)0.052 (2)0.0403 (19)0.0182 (18)0.0159 (17)0.0158 (16)
O20.054 (2)0.051 (2)0.0382 (18)0.0191 (17)0.0113 (16)0.0163 (16)
O30.109 (5)0.151 (6)0.109 (5)0.064 (5)0.038 (4)0.039 (4)
C10.065 (4)0.050 (3)0.060 (3)0.020 (3)0.009 (3)0.018 (3)
C20.073 (4)0.062 (4)0.060 (4)0.040 (3)0.018 (3)0.018 (3)
C30.060 (4)0.068 (4)0.068 (4)0.019 (3)0.018 (3)0.017 (3)
C40.053 (3)0.056 (4)0.062 (4)0.012 (3)0.011 (3)0.023 (3)
C50.068 (4)0.075 (5)0.076 (4)0.008 (4)0.017 (4)0.020 (4)
C60.070 (5)0.078 (5)0.095 (6)0.004 (4)0.018 (4)0.027 (4)
C70.067 (5)0.066 (5)0.092 (5)0.003 (4)0.002 (4)0.022 (4)
C80.072 (4)0.063 (4)0.076 (5)0.010 (4)0.000 (4)0.016 (4)
C90.066 (4)0.063 (4)0.069 (4)0.006 (3)0.009 (3)0.021 (3)
C100.074 (4)0.069 (4)0.056 (3)0.041 (3)0.018 (3)0.028 (3)
C110.085 (5)0.084 (5)0.074 (4)0.052 (4)0.020 (4)0.034 (4)
C120.104 (6)0.082 (5)0.091 (5)0.048 (5)0.017 (4)0.037 (4)
C130.122 (8)0.096 (6)0.108 (7)0.049 (6)0.013 (6)0.044 (5)
C140.120 (8)0.104 (7)0.121 (7)0.063 (7)0.006 (6)0.035 (6)
C150.107 (7)0.118 (8)0.124 (8)0.061 (7)0.016 (6)0.027 (6)
C160.094 (6)0.096 (6)0.102 (6)0.053 (5)0.013 (5)0.035 (5)
C170.063 (4)0.068 (4)0.072 (4)0.025 (3)0.027 (3)0.013 (3)
C180.063 (4)0.063 (4)0.077 (4)0.029 (3)0.022 (3)0.003 (3)
C190.055 (4)0.082 (5)0.064 (4)0.019 (3)0.013 (3)0.032 (3)
C200.050 (3)0.075 (4)0.065 (4)0.026 (3)0.014 (3)0.028 (3)
C210.055 (4)0.090 (5)0.081 (5)0.019 (4)0.009 (3)0.038 (4)
C220.065 (5)0.098 (6)0.089 (5)0.014 (4)0.012 (4)0.043 (4)
C230.060 (5)0.109 (6)0.099 (6)0.013 (4)0.018 (4)0.037 (5)
C240.059 (5)0.111 (7)0.106 (6)0.024 (4)0.005 (4)0.037 (5)
C250.061 (4)0.093 (5)0.089 (5)0.023 (4)0.008 (4)0.040 (4)
C260.093 (5)0.048 (4)0.066 (4)0.029 (3)0.024 (4)0.014 (3)
C270.130 (7)0.059 (4)0.092 (5)0.058 (5)0.027 (5)0.018 (4)
C280.142 (8)0.073 (5)0.107 (7)0.051 (6)0.017 (6)0.012 (5)
C290.150 (9)0.080 (6)0.109 (7)0.043 (6)0.018 (6)0.010 (5)
C300.146 (9)0.069 (5)0.108 (7)0.053 (6)0.030 (6)0.010 (5)
C310.142 (8)0.072 (5)0.111 (7)0.054 (6)0.025 (6)0.015 (5)
C320.137 (8)0.067 (5)0.105 (6)0.053 (5)0.023 (6)0.018 (4)
C330.108 (14)0.147 (17)0.105 (16)0.078 (13)0.030 (12)0.041 (13)
C340.122 (17)0.16 (2)0.12 (2)0.083 (16)0.023 (17)0.045 (19)
C350.129 (19)0.17 (2)0.123 (18)0.079 (17)0.026 (14)0.037 (16)
C33'0.107 (15)0.148 (19)0.106 (16)0.085 (14)0.034 (12)0.041 (13)
C34'0.112 (17)0.148 (19)0.108 (17)0.066 (15)0.025 (13)0.039 (14)
C35'0.128 (19)0.16 (2)0.11 (2)0.081 (18)0.024 (18)0.037 (19)
Geometric parameters (Å, º) top
Ni1—O12.100 (3)C12—H120.9300
Ni1—N12.131 (4)C13—C141.350 (13)
Ni1—N22.143 (4)C13—H130.9300
Ni2—O22.111 (3)C14—C151.377 (13)
Ni2—N32.140 (4)C14—H140.9300
Ni2—N42.130 (4)C15—C161.405 (12)
N1—C31.458 (7)C15—H150.9300
N1—C11.499 (7)C16—H160.9300
N1—H10.9100C17—C181.476 (9)
N2—C21.465 (7)C17—H17A0.9700
N2—C101.469 (7)C17—H17B0.9700
N2—H20.9100C18—H18A0.9700
N3—C191.460 (7)C18—H18B0.9700
N3—C171.482 (7)C19—C201.497 (8)
N3—H30.9100C19—H19A0.9700
N4—C181.455 (7)C19—H19B0.9700
N4—C261.467 (7)C20—C251.371 (9)
N4—H40.9100C20—C211.373 (9)
N5—C331.32 (2)C21—C221.379 (9)
N5—C33'1.34 (2)C21—H210.9300
N5—C34'1.43 (2)C22—C231.359 (11)
N5—C341.44 (2)C22—H220.9300
N5—C35'1.47 (3)C23—C241.372 (11)
N5—C351.48 (2)C23—H230.9300
O1—H1C0.8500C24—C251.391 (10)
O1—H1D0.8500C24—H240.9300
O2—H2C0.8500C25—H250.9300
O2—H2D0.8500C26—C271.490 (9)
O3—C33'1.229 (19)C26—H26A0.9700
O3—C331.25 (2)C26—H26B0.9700
C1—C21.504 (8)C27—C321.372 (11)
C1—H1A0.9700C27—C281.374 (11)
C1—H1B0.9700C28—C291.398 (11)
C2—H2A0.9700C28—H280.9300
C2—H2B0.9700C29—C301.380 (13)
C3—C41.510 (8)C29—H290.9300
C3—H3A0.9700C30—C311.347 (12)
C3—H3B0.9700C30—H300.9300
C4—C51.372 (9)C31—C321.367 (10)
C4—C91.382 (9)C31—H310.9300
C5—C61.380 (10)C32—H320.9300
C5—H50.9300C33—H330.9300
C6—C71.363 (10)C34—H34A0.9600
C6—H60.9300C34—H34B0.9600
C7—C81.360 (10)C34—H34C0.9600
C7—H70.9300C35—H35A0.9600
C8—C91.384 (9)C35—H35B0.9600
C8—H80.9300C35—H35C0.9600
C9—H90.9300C33'—H33'0.9300
C10—C111.505 (8)C34'—H34D0.9600
C10—H10A0.9700C34'—H34E0.9600
C10—H10B0.9700C34'—H34F0.9600
C11—C161.375 (11)C35'—H35D0.9600
C11—C121.383 (10)C35'—H35E0.9600
C12—C131.381 (11)C35'—H35F0.9600
O1—Ni1—O1i180.000 (2)C8—C9—H9118.6
O1—Ni1—N1i88.91 (15)N2—C10—C11115.3 (5)
O1i—Ni1—N1i91.09 (15)N2—C10—H10A108.4
O1—Ni1—N191.09 (15)C11—C10—H10A108.4
O1i—Ni1—N188.91 (15)N2—C10—H10B108.4
N1i—Ni1—N1180.0 (2)C11—C10—H10B108.4
O1—Ni1—N2i84.86 (15)H10A—C10—H10B107.5
O1i—Ni1—N2i95.14 (15)C16—C11—C12118.1 (7)
N1i—Ni1—N2i83.75 (17)C16—C11—C10121.7 (7)
N1—Ni1—N2i96.25 (17)C12—C11—C10120.2 (7)
O1—Ni1—N295.14 (15)C13—C12—C11123.6 (8)
O1i—Ni1—N284.86 (15)C13—C12—H12118.2
N1i—Ni1—N296.25 (17)C11—C12—H12118.2
N1—Ni1—N283.75 (17)C14—C13—C12116.5 (9)
N2i—Ni1—N2180.0 (2)C14—C13—H13121.8
O2ii—Ni2—O2180.000 (1)C12—C13—H13121.8
O2ii—Ni2—N491.57 (15)C13—C14—C15123.2 (9)
O2—Ni2—N488.43 (15)C13—C14—H14118.4
O2ii—Ni2—N4ii88.43 (15)C15—C14—H14118.4
O2—Ni2—N4ii91.57 (15)C14—C15—C16118.8 (10)
N4—Ni2—N4ii180.000 (1)C14—C15—H15120.6
O2ii—Ni2—N390.50 (15)C16—C15—H15120.6
O2—Ni2—N389.50 (15)C11—C16—C15119.7 (9)
N4—Ni2—N383.51 (16)C11—C16—H16120.1
N4ii—Ni2—N396.49 (16)C15—C16—H16120.1
O2ii—Ni2—N3ii89.50 (15)C18—C17—N3112.2 (5)
O2—Ni2—N3ii90.50 (15)C18—C17—H17A109.2
N4—Ni2—N3ii96.49 (16)N3—C17—H17A109.2
N4ii—Ni2—N3ii83.51 (16)C18—C17—H17B109.2
N3—Ni2—N3ii180.000 (1)N3—C17—H17B109.2
C3—N1—C1111.2 (5)H17A—C17—H17B107.9
C3—N1—Ni1119.6 (4)N4—C18—C17111.3 (5)
C1—N1—Ni1105.4 (3)N4—C18—H18A109.4
C3—N1—H1106.6C17—C18—H18A109.4
C1—N1—H1106.6N4—C18—H18B109.4
Ni1—N1—H1106.6C17—C18—H18B109.4
C2—N2—C10113.5 (5)H18A—C18—H18B108.0
C2—N2—Ni1105.1 (3)N3—C19—C20117.5 (5)
C10—N2—Ni1117.4 (3)N3—C19—H19A107.9
C2—N2—H2106.8C20—C19—H19A107.9
C10—N2—H2106.8N3—C19—H19B107.9
Ni1—N2—H2106.8C20—C19—H19B107.9
C19—N3—C17114.1 (5)H19A—C19—H19B107.2
C19—N3—Ni2117.3 (3)C25—C20—C21116.5 (6)
C17—N3—Ni2105.8 (3)C25—C20—C19120.1 (6)
C19—N3—H3106.3C21—C20—C19123.1 (6)
C17—N3—H3106.3C20—C21—C22122.0 (7)
Ni2—N3—H3106.3C20—C21—H21119.0
C18—N4—C26108.8 (5)C22—C21—H21119.0
C18—N4—Ni2106.0 (3)C23—C22—C21120.6 (7)
C26—N4—Ni2117.2 (3)C23—C22—H22119.7
C18—N4—H4108.2C21—C22—H22119.7
C26—N4—H4108.2C22—C23—C24119.0 (7)
Ni2—N4—H4108.2C22—C23—H23120.5
C33—N5—C33'57.9 (12)C24—C23—H23120.5
C33—N5—C34'66.3 (13)C23—C24—C25119.7 (7)
C33'—N5—C34'123.1 (14)C23—C24—H24120.2
C33—N5—C34130.7 (16)C25—C24—H24120.2
C33'—N5—C3472.8 (14)C20—C25—C24122.1 (7)
C34'—N5—C34159.6 (16)C20—C25—H25118.9
C33—N5—C35'168.7 (17)C24—C25—H25118.9
C33'—N5—C35'110.8 (15)N4—C26—C27116.2 (5)
C34'—N5—C35'124.7 (16)N4—C26—H26A108.2
C33—N5—C35111.0 (15)C27—C26—H26A108.2
C33'—N5—C35167.6 (15)N4—C26—H26B108.2
C34'—N5—C3547.9 (11)C27—C26—H26B108.2
C34—N5—C35118.2 (14)H26A—C26—H26B107.4
C35'—N5—C3580.2 (14)C32—C27—C28118.7 (7)
Ni1—O1—H1C110.9C32—C27—C26120.4 (8)
Ni1—O1—H1D111.1C28—C27—C26121.0 (7)
H1C—O1—H1D109.1C27—C28—C29119.0 (9)
Ni2—O2—H2C107.3C27—C28—H28120.5
Ni2—O2—H2D109.3C29—C28—H28120.5
H2C—O2—H2D107.9C30—C29—C28118.6 (10)
C33'—O3—C3362.6 (13)C30—C29—H29120.7
N1—C1—C2109.0 (5)C28—C29—H29120.7
N1—C1—H1A109.9C31—C30—C29123.5 (8)
C2—C1—H1A109.9C31—C30—H30118.2
N1—C1—H1B109.9C29—C30—H30118.2
C2—C1—H1B109.9C30—C31—C32116.1 (9)
H1A—C1—H1B108.3C30—C31—H31121.9
N2—C2—C1110.0 (5)C32—C31—H31121.9
N2—C2—H2A109.7C31—C32—C27123.9 (9)
C1—C2—H2A109.7C31—C32—H32118.0
N2—C2—H2B109.7C27—C32—H32118.0
C1—C2—H2B109.7O3—C33—N5119.8 (17)
H2A—C2—H2B108.2O3—C33—H33120.1
N1—C3—C4115.1 (5)N5—C33—H33120.1
N1—C3—H3A108.5N5—C34—H34A109.5
C4—C3—H3A108.5N5—C34—H34B109.5
N1—C3—H3B108.5N5—C34—H34C109.5
C4—C3—H3B108.5N5—C35—H35A109.5
H3A—C3—H3B107.5N5—C35—H35B109.5
C5—C4—C9116.4 (6)N5—C35—H35C109.5
C5—C4—C3121.3 (6)O3—C33'—N5119.7 (17)
C9—C4—C3122.4 (5)O3—C33'—H33'120.2
C4—C5—C6121.7 (7)N5—C33'—H33'120.2
C4—C5—H5119.1N5—C34'—H34D109.5
C6—C5—H5119.1N5—C34'—H34E109.5
C7—C6—C5120.2 (7)H34D—C34'—H34E109.5
C7—C6—H6119.9N5—C34'—H34F109.5
C5—C6—H6119.9H34D—C34'—H34F109.5
C8—C7—C6120.2 (7)H34E—C34'—H34F109.5
C8—C7—H7119.9N5—C35'—H35D109.5
C6—C7—H7119.9N5—C35'—H35E109.5
C7—C8—C9118.7 (7)H35D—C35'—H35E109.5
C7—C8—H8120.6N5—C35'—H35F109.5
C9—C8—H8120.6H35D—C35'—H35F109.5
C4—C9—C8122.8 (6)H35E—C35'—H35F109.5
C4—C9—H9118.6
O1—Ni1—N1—C344.8 (4)N2—C10—C11—C1669.1 (9)
O1i—Ni1—N1—C3135.2 (4)N2—C10—C11—C12109.3 (7)
N2i—Ni1—N1—C340.2 (4)C16—C11—C12—C130.1 (12)
N2—Ni1—N1—C3139.8 (4)C10—C11—C12—C13178.5 (7)
O1—Ni1—N1—C181.3 (3)C11—C12—C13—C140.6 (13)
O1i—Ni1—N1—C198.7 (3)C12—C13—C14—C151.8 (15)
N2i—Ni1—N1—C1166.2 (3)C13—C14—C15—C162.5 (16)
N2—Ni1—N1—C113.8 (3)C12—C11—C16—C150.7 (12)
O1—Ni1—N2—C2106.3 (3)C10—C11—C16—C15179.2 (7)
O1i—Ni1—N2—C273.7 (3)C14—C15—C16—C111.9 (14)
N1i—Ni1—N2—C2164.2 (3)C19—N3—C17—C1895.7 (6)
N1—Ni1—N2—C215.8 (3)Ni2—N3—C17—C1834.8 (6)
O1—Ni1—N2—C1020.8 (4)C26—N4—C18—C17168.3 (5)
O1i—Ni1—N2—C10159.2 (4)Ni2—N4—C18—C1741.5 (6)
N1i—Ni1—N2—C1068.6 (4)N3—C17—C18—N453.6 (7)
N1—Ni1—N2—C10111.4 (4)C17—N3—C19—C2066.8 (7)
O2ii—Ni2—N3—C19149.0 (4)Ni2—N3—C19—C20168.6 (4)
O2—Ni2—N3—C1931.0 (4)N3—C19—C20—C25143.9 (7)
N4—Ni2—N3—C19119.5 (4)N3—C19—C20—C2141.4 (10)
N4ii—Ni2—N3—C1960.5 (4)C25—C20—C21—C221.4 (11)
O2ii—Ni2—N3—C1782.4 (4)C19—C20—C21—C22176.3 (7)
O2—Ni2—N3—C1797.6 (4)C20—C21—C22—C230.2 (13)
N4—Ni2—N3—C179.1 (4)C21—C22—C23—C241.8 (13)
N4ii—Ni2—N3—C17170.9 (4)C22—C23—C24—C252.5 (13)
O2ii—Ni2—N4—C18107.4 (4)C21—C20—C25—C240.7 (11)
O2—Ni2—N4—C1872.6 (4)C19—C20—C25—C24175.7 (7)
N3—Ni2—N4—C1817.1 (4)C23—C24—C25—C201.2 (13)
N3ii—Ni2—N4—C18162.9 (4)C18—N4—C26—C2763.0 (8)
O2ii—Ni2—N4—C26131.0 (4)Ni2—N4—C26—C27176.8 (5)
O2—Ni2—N4—C2649.0 (4)N4—C26—C27—C32112.1 (9)
N3—Ni2—N4—C26138.7 (4)N4—C26—C27—C2868.1 (11)
N3ii—Ni2—N4—C2641.3 (4)C32—C27—C28—C293.7 (14)
C3—N1—C1—C2172.3 (5)C26—C27—C28—C29176.1 (8)
Ni1—N1—C1—C241.3 (5)C27—C28—C29—C303.1 (15)
C10—N2—C2—C185.9 (6)C28—C29—C30—C310.7 (16)
Ni1—N2—C2—C143.6 (5)C29—C30—C31—C321.1 (16)
N1—C1—C2—N259.5 (6)C30—C31—C32—C270.5 (15)
C1—N1—C3—C455.2 (7)C28—C27—C32—C311.9 (15)
Ni1—N1—C3—C4178.4 (4)C26—C27—C32—C31177.8 (8)
N1—C3—C4—C5133.1 (7)C33'—O3—C33—N51.8 (17)
N1—C3—C4—C948.3 (9)C33'—N5—C33—O31.7 (16)
C9—C4—C5—C60.4 (11)C34'—N5—C33—O3166 (2)
C3—C4—C5—C6179.1 (7)C34—N5—C33—O30 (3)
C4—C5—C6—C71.3 (13)C35'—N5—C33—O33 (10)
C5—C6—C7—C81.7 (13)C35—N5—C33—O3175.5 (17)
C6—C7—C8—C90.3 (12)C33—O3—C33'—N51.8 (17)
C5—C4—C9—C81.9 (10)C33—N5—C33'—O31.7 (17)
C3—C4—C9—C8179.4 (6)C34'—N5—C33'—O311 (3)
C7—C8—C9—C41.5 (11)C34—N5—C33'—O3177 (2)
C2—N2—C10—C1153.8 (7)C35'—N5—C33'—O3179 (2)
Ni1—N2—C10—C11176.8 (5)C35—N5—C33'—O330 (8)
Symmetry codes: (i) x+1, y+1, z+2; (ii) x+1, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1C···Cl20.852.263.055 (4)155
O1—H1D···Cl1ii0.852.243.078 (4)169
O2—H2C···Cl1ii0.852.243.071 (4)168
O2—H2D···Cl20.852.193.041 (4)174
N1—H1···Cl1iii0.912.543.444 (4)171
N2—H2···O3i0.912.203.102 (8)169
N3—H3···Cl10.912.553.400 (4)155
N4—H4···Cl2ii0.912.543.428 (5)167
Symmetry codes: (i) x+1, y+1, z+2; (ii) x+1, y+1, z+1; (iii) x, y, z+1.

Experimental details

Crystal data
Chemical formula[Ni(C16H20N2)2(H2O)2]Cl2·C3H7NO
Mr719.42
Crystal system, space groupTriclinic, P1
Temperature (K)298
a, b, c (Å)11.898 (1), 12.588 (1), 14.872 (2)
α, β, γ (°)104.769 (2), 95.368 (1), 111.399 (2)
V3)1961.8 (3)
Z2
Radiation typeMo Kα
µ (mm1)0.67
Crystal size (mm)0.42 × 0.40 × 0.35
Data collection
DiffractometerSiemens SMART 1000 CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.767, 0.800
No. of measured, independent and
observed [I > 2σ(I)] reflections
10138, 6781, 4690
Rint0.018
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.066, 0.201, 1.02
No. of reflections6781
No. of parameters450
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)1.15, 0.75

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top
Ni1—O12.100 (3)Ni2—O22.111 (3)
Ni1—N12.131 (4)Ni2—N32.140 (4)
Ni1—N22.143 (4)Ni2—N42.130 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1C···Cl20.852.263.055 (4)155
O1—H1D···Cl1i0.852.243.078 (4)169
O2—H2C···Cl1i0.852.243.071 (4)168
O2—H2D···Cl20.852.193.041 (4)174
N1—H1···Cl1ii0.912.543.444 (4)171
N2—H2···O3iii0.912.203.102 (8)169
N3—H3···Cl10.912.553.400 (4)155
N4—H4···Cl2i0.912.543.428 (5)167
Symmetry codes: (i) x+1, y+1, z+1; (ii) x, y, z+1; (iii) x+1, y+1, z+2.
 

Acknowledgements

We acknowledge financial support by the Science Foundation of Huaihai Institute of Technology and the Department of Chemical Engineering.

References

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 citationSiemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.  Google Scholar
First citationXia, H.-T., Liu, Y.-F., Wang, D.-Q. & Yang, S.-P. (2007a). Acta Cryst. E63, m1162–m1164.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationXia, H.-T., Liu, Y.-F., Wang, D.-Q. & Yang, S.-P. (2007b). Acta Cryst. E63, m2512–m2513.  Web of Science CSD CrossRef IUCr Journals Google Scholar

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Volume 65| Part 12| December 2009| Pages m1526-m1527
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