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

Liu, Y.-F.; Xia, H.-T.; Wang, D.-Q.; Gong, X.-L.

doi:10.1107/S1600536809046042

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

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

doi:10.1107/S1600536809046042

Open

access

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

Yu-Fen Liu,^a Hai-Tao Xia,^a ^* Da-Qi Wang ^b and Xiao-Lin Gong ^a

^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 Ni^II 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 Ni^II 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 ,b ).

Experimental

Crystal data

[Ni(C₁₆H₂₀N₂)₂(H₂O)₂]Cl₂·C₃H₇NO
M_r = 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 ) T_min = 0.767, T_max = 0.800
10138 measured reflections
6781 independent reflections
4690 reflections with I > 2σ(I)
R_int = 0.018

Refinement

R[F² > 2σ(F²)] = 0.066
wR(F²) = 0.201
S = 1.02
6781 reflections
450 parameters
H-atom parameters constrained
Δρ_max = 1.15 e Å⁻³
Δρ_min = −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	D⋯A	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 ); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; 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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809046042/hy2244sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809046042/hy2244Isup2.hkl

checkCIF report

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 Ni^II 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.

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

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·C₃H₇NO	Z = 2
M_r = 719.42	F(000) = 764
Triclinic, P1	D_x = 1.218 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 11.898 (1) Å	Cell parameters from 3426 reflections
b = 12.588 (1) Å	θ = 2.4–28.9°
c = 14.872 (2) Å	µ = 0.67 mm⁻¹
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 tube	4690 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.018
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −14→12
T_min = 0.767, T_max = 0.800	k = −14→14
10138 measured reflections	l = −15→17

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.066	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.201	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0878P)² + 5.0932P] where P = (F_o² + 2F_c²)/3
6781 reflections	(Δ/σ)_max = 0.001
450 parameters	Δρ_max = 1.15 e Å⁻³
0 restraints	Δρ_min = −0.75 e Å⁻³

Crystal data top

[Ni(C₁₆H₂₀N₂)₂(H₂O)₂]Cl₂·C₃H₇NO	γ = 111.399 (2)°
M_r = 719.42	V = 1961.8 (3) Å³
Triclinic, P1	Z = 2
a = 11.898 (1) Å	Mo Kα radiation
b = 12.588 (1) Å	µ = 0.67 mm⁻¹
c = 14.872 (2) Å	T = 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)
T_min = 0.767, T_max = 0.800	R_int = 0.018
10138 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.066	0 restraints
wR(F²) = 0.201	H-atom parameters constrained
S = 1.02	Δρ_max = 1.15 e Å⁻³
6781 reflections	Δρ_min = −0.75 e Å⁻³
450 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
Ni1	0.5000	0.5000	1.0000	0.0360 (2)
Ni2	0.5000	0.5000	0.5000	0.0373 (2)
Cl1	0.61243 (14)	0.70108 (13)	0.30429 (9)	0.0584 (4)
Cl2	0.68699 (16)	0.69555 (13)	0.79097 (10)	0.0709 (5)
N1	0.6479 (4)	0.6692 (4)	1.0730 (3)	0.0487 (10)
H1	0.6481	0.6822	1.1361	0.058*
N2	0.4030 (4)	0.6078 (4)	0.9772 (3)	0.0523 (11)
H2	0.3301	0.5789	0.9959	0.063*
N3	0.6784 (4)	0.5756 (4)	0.4682 (3)	0.0459 (10)
H3	0.6763	0.6311	0.4398	0.055*
N4	0.4979 (4)	0.3356 (4)	0.4135 (3)	0.0465 (10)
H4	0.4540	0.3180	0.3543	0.056*
N5	0.8816 (7)	0.4000 (8)	0.7989 (6)	0.113 (2)
O1	0.5688 (3)	0.4934 (3)	0.8746 (2)	0.0506 (9)
H1C	0.5980	0.5626	0.8676	0.061*
H1D	0.5127	0.4452	0.8263	0.061*
O2	0.5814 (3)	0.4709 (3)	0.6187 (2)	0.0479 (8)
H2C	0.5255	0.4151	0.6315	0.057*
H2D	0.6057	0.5340	0.6663	0.057*
O3	0.8337 (6)	0.4541 (7)	0.9394 (5)	0.118 (2)
C1	0.6111 (6)	0.7603 (5)	1.0454 (4)	0.0594 (15)
H1A	0.6266	0.7620	0.9828	0.071*
H1B	0.6594	0.8395	1.0904	0.071*
C2	0.4762 (6)	0.7274 (5)	1.0450 (4)	0.0616 (15)
H2A	0.4614	0.7281	1.1081	0.074*
H2B	0.4514	0.7860	1.0274	0.074*
C3	0.7735 (6)	0.6875 (6)	1.0621 (5)	0.0678 (17)
H3A	0.7754	0.6708	0.9950	0.081*
H3B	0.7951	0.6297	1.0839	0.081*
C4	0.8705 (5)	0.8117 (5)	1.1149 (4)	0.0595 (15)
C5	0.9575 (6)	0.8730 (6)	1.0714 (5)	0.079 (2)
H5	0.9558	0.8375	1.0079	0.095*
C6	1.0475 (7)	0.9859 (7)	1.1193 (6)	0.091 (2)
H6	1.1064	1.0247	1.0884	0.109*
C7	1.0504 (7)	1.0406 (7)	1.2117 (6)	0.084 (2)
H7	1.1098	1.1176	1.2433	0.101*
C8	0.9665 (6)	0.9831 (6)	1.2580 (5)	0.0779 (19)
H8	0.9681	1.0198	1.3212	0.093*
C9	0.8785 (6)	0.8689 (6)	1.2093 (5)	0.0721 (18)
H9	0.8225	0.8289	1.2415	0.087*
C10	0.3726 (6)	0.6090 (6)	0.8795 (4)	0.0608 (15)
H10A	0.3191	0.5279	0.8402	0.073*
H10B	0.4482	0.6323	0.8556	0.073*
C11	0.3108 (7)	0.6912 (7)	0.8681 (5)	0.0738 (18)
C12	0.3740 (8)	0.7947 (7)	0.8463 (5)	0.087 (2)
H12	0.4542	0.8104	0.8376	0.105*
C13	0.3246 (10)	0.8759 (8)	0.8368 (6)	0.105 (3)
H13	0.3690	0.9444	0.8215	0.127*
C14	0.2083 (11)	0.8505 (9)	0.8508 (7)	0.111 (3)
H14	0.1736	0.9048	0.8466	0.134*
C15	0.1388 (10)	0.7483 (10)	0.8709 (7)	0.114 (3)
H15	0.0579	0.7326	0.8776	0.137*
C16	0.1923 (8)	0.6681 (8)	0.8810 (6)	0.093 (2)
H16	0.1477	0.5998	0.8964	0.111*
C17	0.6887 (6)	0.4775 (6)	0.3940 (5)	0.0690 (17)
H17A	0.6532	0.4758	0.3320	0.083*
H17B	0.7752	0.4935	0.3959	0.083*
C18	0.6255 (6)	0.3591 (6)	0.4070 (5)	0.0700 (18)
H18A	0.6277	0.2969	0.3538	0.084*
H18B	0.6687	0.3565	0.4645	0.084*
C19	0.7840 (6)	0.6380 (6)	0.5480 (4)	0.0681 (17)
H19A	0.7954	0.5786	0.5742	0.082*
H19B	0.7632	0.6910	0.5969	0.082*
C20	0.9051 (5)	0.7107 (6)	0.5289 (4)	0.0619 (15)
C21	0.9161 (6)	0.7821 (7)	0.4713 (5)	0.0765 (19)
H21	0.8450	0.7824	0.4397	0.092*
C22	1.0293 (7)	0.8535 (7)	0.4590 (6)	0.088 (2)
H22	1.0333	0.9006	0.4193	0.105*
C23	1.1351 (7)	0.8556 (8)	0.5043 (6)	0.094 (2)
H23	1.2113	0.9020	0.4945	0.113*
C24	1.1279 (7)	0.7882 (8)	0.5646 (6)	0.095 (2)
H24	1.1994	0.7909	0.5981	0.115*
C25	1.0129 (6)	0.7157 (7)	0.5754 (5)	0.082 (2)
H25	1.0090	0.6692	0.6156	0.098*
C26	0.4477 (7)	0.2302 (5)	0.4460 (5)	0.0692 (17)
H26A	0.3652	0.2195	0.4555	0.083*
H26B	0.4979	0.2469	0.5073	0.083*
C27	0.4410 (9)	0.1149 (6)	0.3818 (6)	0.088 (2)
C28	0.3607 (10)	0.0594 (7)	0.2950 (7)	0.109 (3)
H28	0.3129	0.0956	0.2734	0.131*
C29	0.3520 (11)	−0.0524 (8)	0.2396 (7)	0.119 (3)
H29	0.2956	−0.0935	0.1820	0.142*
C30	0.4289 (10)	−0.1003 (8)	0.2721 (7)	0.108 (3)
H30	0.4233	−0.1743	0.2347	0.130*
C31	0.5115 (10)	−0.0458 (8)	0.3553 (7)	0.108 (3)
H31	0.5633	−0.0793	0.3752	0.130*
C32	0.5149 (9)	0.0617 (7)	0.4086 (6)	0.102 (3)
H32	0.5707	0.1011	0.4666	0.122*
C33	0.8308 (18)	0.4586 (19)	0.8564 (15)	0.111 (8)	0.52 (2)
H33	0.7930	0.5032	0.8351	0.133*	0.52 (2)
C34	0.945 (3)	0.326 (3)	0.814 (2)	0.125 (8)	0.52 (2)
H34A	0.9647	0.3377	0.8813	0.187*	0.52 (2)
H34B	1.0198	0.3480	0.7907	0.187*	0.52 (2)
H34C	0.8930	0.2431	0.7819	0.187*	0.52 (2)
C35	0.877 (2)	0.425 (2)	0.7071 (17)	0.137 (9)	0.52 (2)
H35A	0.8074	0.3613	0.6612	0.206*	0.52 (2)
H35B	0.9513	0.4304	0.6853	0.206*	0.52 (2)
H35C	0.8680	0.4996	0.7153	0.206*	0.52 (2)
C33'	0.8850 (18)	0.400 (2)	0.8893 (16)	0.109 (8)	0.48 (2)
H33'	0.9258	0.3605	0.9140	0.130*	0.48 (2)
C34'	0.803 (2)	0.441 (2)	0.7512 (16)	0.119 (8)	0.48 (2)
H34D	0.7266	0.4207	0.7722	0.178*	0.48 (2)
H34E	0.7880	0.4038	0.6838	0.178*	0.48 (2)
H34F	0.8431	0.5268	0.7656	0.178*	0.48 (2)
C35'	0.946 (3)	0.329 (3)	0.751 (2)	0.128 (9)	0.48 (2)
H35D	1.0249	0.3525	0.7903	0.193*	0.48 (2)
H35E	0.9559	0.3417	0.6912	0.193*	0.48 (2)
H35F	0.8974	0.2450	0.7411	0.193*	0.48 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.0397 (5)	0.0367 (5)	0.0311 (4)	0.0144 (4)	0.0077 (3)	0.0110 (4)
Ni2	0.0429 (5)	0.0381 (5)	0.0319 (4)	0.0171 (4)	0.0097 (4)	0.0107 (4)
Cl1	0.0708 (9)	0.0528 (8)	0.0422 (7)	0.0125 (7)	0.0107 (6)	0.0183 (6)
Cl2	0.0868 (11)	0.0541 (9)	0.0448 (8)	−0.0003 (8)	0.0074 (7)	0.0159 (6)
N1	0.050 (3)	0.047 (3)	0.047 (2)	0.016 (2)	0.013 (2)	0.013 (2)
N2	0.059 (3)	0.055 (3)	0.051 (3)	0.030 (2)	0.012 (2)	0.021 (2)
N3	0.046 (2)	0.051 (3)	0.048 (2)	0.023 (2)	0.015 (2)	0.020 (2)
N4	0.054 (3)	0.044 (2)	0.044 (2)	0.023 (2)	0.015 (2)	0.0112 (19)
N5	0.109 (6)	0.158 (8)	0.100 (6)	0.083 (6)	0.037 (5)	0.038 (5)
O1	0.058 (2)	0.052 (2)	0.0403 (19)	0.0182 (18)	0.0159 (17)	0.0158 (16)
O2	0.054 (2)	0.051 (2)	0.0382 (18)	0.0191 (17)	0.0113 (16)	0.0163 (16)
O3	0.109 (5)	0.151 (6)	0.109 (5)	0.064 (5)	0.038 (4)	0.039 (4)
C1	0.065 (4)	0.050 (3)	0.060 (3)	0.020 (3)	0.009 (3)	0.018 (3)
C2	0.073 (4)	0.062 (4)	0.060 (4)	0.040 (3)	0.018 (3)	0.018 (3)
C3	0.060 (4)	0.068 (4)	0.068 (4)	0.019 (3)	0.018 (3)	0.017 (3)
C4	0.053 (3)	0.056 (4)	0.062 (4)	0.012 (3)	0.011 (3)	0.023 (3)
C5	0.068 (4)	0.075 (5)	0.076 (4)	0.008 (4)	0.017 (4)	0.020 (4)
C6	0.070 (5)	0.078 (5)	0.095 (6)	−0.004 (4)	0.018 (4)	0.027 (4)
C7	0.067 (5)	0.066 (5)	0.092 (5)	0.003 (4)	−0.002 (4)	0.022 (4)
C8	0.072 (4)	0.063 (4)	0.076 (5)	0.010 (4)	0.000 (4)	0.016 (4)
C9	0.066 (4)	0.063 (4)	0.069 (4)	0.006 (3)	0.009 (3)	0.021 (3)
C10	0.074 (4)	0.069 (4)	0.056 (3)	0.041 (3)	0.018 (3)	0.028 (3)
C11	0.085 (5)	0.084 (5)	0.074 (4)	0.052 (4)	0.020 (4)	0.034 (4)
C12	0.104 (6)	0.082 (5)	0.091 (5)	0.048 (5)	0.017 (4)	0.037 (4)
C13	0.122 (8)	0.096 (6)	0.108 (7)	0.049 (6)	0.013 (6)	0.044 (5)
C14	0.120 (8)	0.104 (7)	0.121 (7)	0.063 (7)	0.006 (6)	0.035 (6)
C15	0.107 (7)	0.118 (8)	0.124 (8)	0.061 (7)	0.016 (6)	0.027 (6)
C16	0.094 (6)	0.096 (6)	0.102 (6)	0.053 (5)	0.013 (5)	0.035 (5)
C17	0.063 (4)	0.068 (4)	0.072 (4)	0.025 (3)	0.027 (3)	0.013 (3)
C18	0.063 (4)	0.063 (4)	0.077 (4)	0.029 (3)	0.022 (3)	0.003 (3)
C19	0.055 (4)	0.082 (5)	0.064 (4)	0.019 (3)	0.013 (3)	0.032 (3)
C20	0.050 (3)	0.075 (4)	0.065 (4)	0.026 (3)	0.014 (3)	0.028 (3)
C21	0.055 (4)	0.090 (5)	0.081 (5)	0.019 (4)	0.009 (3)	0.038 (4)
C22	0.065 (5)	0.098 (6)	0.089 (5)	0.014 (4)	0.012 (4)	0.043 (4)
C23	0.060 (5)	0.109 (6)	0.099 (6)	0.013 (4)	0.018 (4)	0.037 (5)
C24	0.059 (5)	0.111 (7)	0.106 (6)	0.024 (4)	0.005 (4)	0.037 (5)
C25	0.061 (4)	0.093 (5)	0.089 (5)	0.023 (4)	0.008 (4)	0.040 (4)
C26	0.093 (5)	0.048 (4)	0.066 (4)	0.029 (3)	0.024 (4)	0.014 (3)
C27	0.130 (7)	0.059 (4)	0.092 (5)	0.058 (5)	0.027 (5)	0.018 (4)
C28	0.142 (8)	0.073 (5)	0.107 (7)	0.051 (6)	0.017 (6)	0.012 (5)
C29	0.150 (9)	0.080 (6)	0.109 (7)	0.043 (6)	0.018 (6)	0.010 (5)
C30	0.146 (9)	0.069 (5)	0.108 (7)	0.053 (6)	0.030 (6)	0.010 (5)
C31	0.142 (8)	0.072 (5)	0.111 (7)	0.054 (6)	0.025 (6)	0.015 (5)
C32	0.137 (8)	0.067 (5)	0.105 (6)	0.053 (5)	0.023 (6)	0.018 (4)
C33	0.108 (14)	0.147 (17)	0.105 (16)	0.078 (13)	0.030 (12)	0.041 (13)
C34	0.122 (17)	0.16 (2)	0.12 (2)	0.083 (16)	0.023 (17)	0.045 (19)
C35	0.129 (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—O1	2.100 (3)	C12—H12	0.9300
Ni1—N1	2.131 (4)	C13—C14	1.350 (13)
Ni1—N2	2.143 (4)	C13—H13	0.9300
Ni2—O2	2.111 (3)	C14—C15	1.377 (13)
Ni2—N3	2.140 (4)	C14—H14	0.9300
Ni2—N4	2.130 (4)	C15—C16	1.405 (12)
N1—C3	1.458 (7)	C15—H15	0.9300
N1—C1	1.499 (7)	C16—H16	0.9300
N1—H1	0.9100	C17—C18	1.476 (9)
N2—C2	1.465 (7)	C17—H17A	0.9700
N2—C10	1.469 (7)	C17—H17B	0.9700
N2—H2	0.9100	C18—H18A	0.9700
N3—C19	1.460 (7)	C18—H18B	0.9700
N3—C17	1.482 (7)	C19—C20	1.497 (8)
N3—H3	0.9100	C19—H19A	0.9700
N4—C18	1.455 (7)	C19—H19B	0.9700
N4—C26	1.467 (7)	C20—C25	1.371 (9)
N4—H4	0.9100	C20—C21	1.373 (9)
N5—C33	1.32 (2)	C21—C22	1.379 (9)
N5—C33'	1.34 (2)	C21—H21	0.9300
N5—C34'	1.43 (2)	C22—C23	1.359 (11)
N5—C34	1.44 (2)	C22—H22	0.9300
N5—C35'	1.47 (3)	C23—C24	1.372 (11)
N5—C35	1.48 (2)	C23—H23	0.9300
O1—H1C	0.8500	C24—C25	1.391 (10)
O1—H1D	0.8500	C24—H24	0.9300
O2—H2C	0.8500	C25—H25	0.9300
O2—H2D	0.8500	C26—C27	1.490 (9)
O3—C33'	1.229 (19)	C26—H26A	0.9700
O3—C33	1.25 (2)	C26—H26B	0.9700
C1—C2	1.504 (8)	C27—C32	1.372 (11)
C1—H1A	0.9700	C27—C28	1.374 (11)
C1—H1B	0.9700	C28—C29	1.398 (11)
C2—H2A	0.9700	C28—H28	0.9300
C2—H2B	0.9700	C29—C30	1.380 (13)
C3—C4	1.510 (8)	C29—H29	0.9300
C3—H3A	0.9700	C30—C31	1.347 (12)
C3—H3B	0.9700	C30—H30	0.9300
C4—C5	1.372 (9)	C31—C32	1.367 (10)
C4—C9	1.382 (9)	C31—H31	0.9300
C5—C6	1.380 (10)	C32—H32	0.9300
C5—H5	0.9300	C33—H33	0.9300
C6—C7	1.363 (10)	C34—H34A	0.9600
C6—H6	0.9300	C34—H34B	0.9600
C7—C8	1.360 (10)	C34—H34C	0.9600
C7—H7	0.9300	C35—H35A	0.9600
C8—C9	1.384 (9)	C35—H35B	0.9600
C8—H8	0.9300	C35—H35C	0.9600
C9—H9	0.9300	C33'—H33'	0.9300
C10—C11	1.505 (8)	C34'—H34D	0.9600
C10—H10A	0.9700	C34'—H34E	0.9600
C10—H10B	0.9700	C34'—H34F	0.9600
C11—C16	1.375 (11)	C35'—H35D	0.9600
C11—C12	1.383 (10)	C35'—H35E	0.9600
C12—C13	1.381 (11)	C35'—H35F	0.9600

O1—Ni1—O1ⁱ	180.000 (2)	C8—C9—H9	118.6
O1—Ni1—N1ⁱ	88.91 (15)	N2—C10—C11	115.3 (5)
O1ⁱ—Ni1—N1ⁱ	91.09 (15)	N2—C10—H10A	108.4
O1—Ni1—N1	91.09 (15)	C11—C10—H10A	108.4
O1ⁱ—Ni1—N1	88.91 (15)	N2—C10—H10B	108.4
N1ⁱ—Ni1—N1	180.0 (2)	C11—C10—H10B	108.4
O1—Ni1—N2ⁱ	84.86 (15)	H10A—C10—H10B	107.5
O1ⁱ—Ni1—N2ⁱ	95.14 (15)	C16—C11—C12	118.1 (7)
N1ⁱ—Ni1—N2ⁱ	83.75 (17)	C16—C11—C10	121.7 (7)
N1—Ni1—N2ⁱ	96.25 (17)	C12—C11—C10	120.2 (7)
O1—Ni1—N2	95.14 (15)	C13—C12—C11	123.6 (8)
O1ⁱ—Ni1—N2	84.86 (15)	C13—C12—H12	118.2
N1ⁱ—Ni1—N2	96.25 (17)	C11—C12—H12	118.2
N1—Ni1—N2	83.75 (17)	C14—C13—C12	116.5 (9)
N2ⁱ—Ni1—N2	180.0 (2)	C14—C13—H13	121.8
O2ⁱⁱ—Ni2—O2	180.000 (1)	C12—C13—H13	121.8
O2ⁱⁱ—Ni2—N4	91.57 (15)	C13—C14—C15	123.2 (9)
O2—Ni2—N4	88.43 (15)	C13—C14—H14	118.4
O2ⁱⁱ—Ni2—N4ⁱⁱ	88.43 (15)	C15—C14—H14	118.4
O2—Ni2—N4ⁱⁱ	91.57 (15)	C14—C15—C16	118.8 (10)
N4—Ni2—N4ⁱⁱ	180.000 (1)	C14—C15—H15	120.6
O2ⁱⁱ—Ni2—N3	90.50 (15)	C16—C15—H15	120.6
O2—Ni2—N3	89.50 (15)	C11—C16—C15	119.7 (9)
N4—Ni2—N3	83.51 (16)	C11—C16—H16	120.1
N4ⁱⁱ—Ni2—N3	96.49 (16)	C15—C16—H16	120.1
O2ⁱⁱ—Ni2—N3ⁱⁱ	89.50 (15)	C18—C17—N3	112.2 (5)
O2—Ni2—N3ⁱⁱ	90.50 (15)	C18—C17—H17A	109.2
N4—Ni2—N3ⁱⁱ	96.49 (16)	N3—C17—H17A	109.2
N4ⁱⁱ—Ni2—N3ⁱⁱ	83.51 (16)	C18—C17—H17B	109.2
N3—Ni2—N3ⁱⁱ	180.000 (1)	N3—C17—H17B	109.2
C3—N1—C1	111.2 (5)	H17A—C17—H17B	107.9
C3—N1—Ni1	119.6 (4)	N4—C18—C17	111.3 (5)
C1—N1—Ni1	105.4 (3)	N4—C18—H18A	109.4
C3—N1—H1	106.6	C17—C18—H18A	109.4
C1—N1—H1	106.6	N4—C18—H18B	109.4
Ni1—N1—H1	106.6	C17—C18—H18B	109.4
C2—N2—C10	113.5 (5)	H18A—C18—H18B	108.0
C2—N2—Ni1	105.1 (3)	N3—C19—C20	117.5 (5)
C10—N2—Ni1	117.4 (3)	N3—C19—H19A	107.9
C2—N2—H2	106.8	C20—C19—H19A	107.9
C10—N2—H2	106.8	N3—C19—H19B	107.9
Ni1—N2—H2	106.8	C20—C19—H19B	107.9
C19—N3—C17	114.1 (5)	H19A—C19—H19B	107.2
C19—N3—Ni2	117.3 (3)	C25—C20—C21	116.5 (6)
C17—N3—Ni2	105.8 (3)	C25—C20—C19	120.1 (6)
C19—N3—H3	106.3	C21—C20—C19	123.1 (6)
C17—N3—H3	106.3	C20—C21—C22	122.0 (7)
Ni2—N3—H3	106.3	C20—C21—H21	119.0
C18—N4—C26	108.8 (5)	C22—C21—H21	119.0
C18—N4—Ni2	106.0 (3)	C23—C22—C21	120.6 (7)
C26—N4—Ni2	117.2 (3)	C23—C22—H22	119.7
C18—N4—H4	108.2	C21—C22—H22	119.7
C26—N4—H4	108.2	C22—C23—C24	119.0 (7)
Ni2—N4—H4	108.2	C22—C23—H23	120.5
C33—N5—C33'	57.9 (12)	C24—C23—H23	120.5
C33—N5—C34'	66.3 (13)	C23—C24—C25	119.7 (7)
C33'—N5—C34'	123.1 (14)	C23—C24—H24	120.2
C33—N5—C34	130.7 (16)	C25—C24—H24	120.2
C33'—N5—C34	72.8 (14)	C20—C25—C24	122.1 (7)
C34'—N5—C34	159.6 (16)	C20—C25—H25	118.9
C33—N5—C35'	168.7 (17)	C24—C25—H25	118.9
C33'—N5—C35'	110.8 (15)	N4—C26—C27	116.2 (5)
C34'—N5—C35'	124.7 (16)	N4—C26—H26A	108.2
C33—N5—C35	111.0 (15)	C27—C26—H26A	108.2
C33'—N5—C35	167.6 (15)	N4—C26—H26B	108.2
C34'—N5—C35	47.9 (11)	C27—C26—H26B	108.2
C34—N5—C35	118.2 (14)	H26A—C26—H26B	107.4
C35'—N5—C35	80.2 (14)	C32—C27—C28	118.7 (7)
Ni1—O1—H1C	110.9	C32—C27—C26	120.4 (8)
Ni1—O1—H1D	111.1	C28—C27—C26	121.0 (7)
H1C—O1—H1D	109.1	C27—C28—C29	119.0 (9)
Ni2—O2—H2C	107.3	C27—C28—H28	120.5
Ni2—O2—H2D	109.3	C29—C28—H28	120.5
H2C—O2—H2D	107.9	C30—C29—C28	118.6 (10)
C33'—O3—C33	62.6 (13)	C30—C29—H29	120.7
N1—C1—C2	109.0 (5)	C28—C29—H29	120.7
N1—C1—H1A	109.9	C31—C30—C29	123.5 (8)
C2—C1—H1A	109.9	C31—C30—H30	118.2
N1—C1—H1B	109.9	C29—C30—H30	118.2
C2—C1—H1B	109.9	C30—C31—C32	116.1 (9)
H1A—C1—H1B	108.3	C30—C31—H31	121.9
N2—C2—C1	110.0 (5)	C32—C31—H31	121.9
N2—C2—H2A	109.7	C31—C32—C27	123.9 (9)
C1—C2—H2A	109.7	C31—C32—H32	118.0
N2—C2—H2B	109.7	C27—C32—H32	118.0
C1—C2—H2B	109.7	O3—C33—N5	119.8 (17)
H2A—C2—H2B	108.2	O3—C33—H33	120.1
N1—C3—C4	115.1 (5)	N5—C33—H33	120.1
N1—C3—H3A	108.5	N5—C34—H34A	109.5
C4—C3—H3A	108.5	N5—C34—H34B	109.5
N1—C3—H3B	108.5	N5—C34—H34C	109.5
C4—C3—H3B	108.5	N5—C35—H35A	109.5
H3A—C3—H3B	107.5	N5—C35—H35B	109.5
C5—C4—C9	116.4 (6)	N5—C35—H35C	109.5
C5—C4—C3	121.3 (6)	O3—C33'—N5	119.7 (17)
C9—C4—C3	122.4 (5)	O3—C33'—H33'	120.2
C4—C5—C6	121.7 (7)	N5—C33'—H33'	120.2
C4—C5—H5	119.1	N5—C34'—H34D	109.5
C6—C5—H5	119.1	N5—C34'—H34E	109.5
C7—C6—C5	120.2 (7)	H34D—C34'—H34E	109.5
C7—C6—H6	119.9	N5—C34'—H34F	109.5
C5—C6—H6	119.9	H34D—C34'—H34F	109.5
C8—C7—C6	120.2 (7)	H34E—C34'—H34F	109.5
C8—C7—H7	119.9	N5—C35'—H35D	109.5
C6—C7—H7	119.9	N5—C35'—H35E	109.5
C7—C8—C9	118.7 (7)	H35D—C35'—H35E	109.5
C7—C8—H8	120.6	N5—C35'—H35F	109.5
C9—C8—H8	120.6	H35D—C35'—H35F	109.5
C4—C9—C8	122.8 (6)	H35E—C35'—H35F	109.5
C4—C9—H9	118.6

O1—Ni1—N1—C3	−44.8 (4)	N2—C10—C11—C16	−69.1 (9)
O1ⁱ—Ni1—N1—C3	135.2 (4)	N2—C10—C11—C12	109.3 (7)
N2ⁱ—Ni1—N1—C3	40.2 (4)	C16—C11—C12—C13	−0.1 (12)
N2—Ni1—N1—C3	−139.8 (4)	C10—C11—C12—C13	−178.5 (7)
O1—Ni1—N1—C1	81.3 (3)	C11—C12—C13—C14	0.6 (13)
O1ⁱ—Ni1—N1—C1	−98.7 (3)	C12—C13—C14—C15	−1.8 (15)
N2ⁱ—Ni1—N1—C1	166.2 (3)	C13—C14—C15—C16	2.5 (16)
N2—Ni1—N1—C1	−13.8 (3)	C12—C11—C16—C15	0.7 (12)
O1—Ni1—N2—C2	−106.3 (3)	C10—C11—C16—C15	179.2 (7)
O1ⁱ—Ni1—N2—C2	73.7 (3)	C14—C15—C16—C11	−1.9 (14)
N1ⁱ—Ni1—N2—C2	164.2 (3)	C19—N3—C17—C18	95.7 (6)
N1—Ni1—N2—C2	−15.8 (3)	Ni2—N3—C17—C18	−34.8 (6)
O1—Ni1—N2—C10	20.8 (4)	C26—N4—C18—C17	−168.3 (5)
O1ⁱ—Ni1—N2—C10	−159.2 (4)	Ni2—N4—C18—C17	−41.5 (6)
N1ⁱ—Ni1—N2—C10	−68.6 (4)	N3—C17—C18—N4	53.6 (7)
N1—Ni1—N2—C10	111.4 (4)	C17—N3—C19—C20	66.8 (7)
O2ⁱⁱ—Ni2—N3—C19	149.0 (4)	Ni2—N3—C19—C20	−168.6 (4)
O2—Ni2—N3—C19	−31.0 (4)	N3—C19—C20—C25	−143.9 (7)
N4—Ni2—N3—C19	−119.5 (4)	N3—C19—C20—C21	41.4 (10)
N4ⁱⁱ—Ni2—N3—C19	60.5 (4)	C25—C20—C21—C22	1.4 (11)
O2ⁱⁱ—Ni2—N3—C17	−82.4 (4)	C19—C20—C21—C22	176.3 (7)
O2—Ni2—N3—C17	97.6 (4)	C20—C21—C22—C23	−0.2 (13)
N4—Ni2—N3—C17	9.1 (4)	C21—C22—C23—C24	−1.8 (13)
N4ⁱⁱ—Ni2—N3—C17	−170.9 (4)	C22—C23—C24—C25	2.5 (13)
O2ⁱⁱ—Ni2—N4—C18	107.4 (4)	C21—C20—C25—C24	−0.7 (11)
O2—Ni2—N4—C18	−72.6 (4)	C19—C20—C25—C24	−175.7 (7)
N3—Ni2—N4—C18	17.1 (4)	C23—C24—C25—C20	−1.2 (13)
N3ⁱⁱ—Ni2—N4—C18	−162.9 (4)	C18—N4—C26—C27	−63.0 (8)
O2ⁱⁱ—Ni2—N4—C26	−131.0 (4)	Ni2—N4—C26—C27	176.8 (5)
O2—Ni2—N4—C26	49.0 (4)	N4—C26—C27—C32	112.1 (9)
N3—Ni2—N4—C26	138.7 (4)	N4—C26—C27—C28	−68.1 (11)
N3ⁱⁱ—Ni2—N4—C26	−41.3 (4)	C32—C27—C28—C29	3.7 (14)
C3—N1—C1—C2	172.3 (5)	C26—C27—C28—C29	−176.1 (8)
Ni1—N1—C1—C2	41.3 (5)	C27—C28—C29—C30	−3.1 (15)
C10—N2—C2—C1	−85.9 (6)	C28—C29—C30—C31	0.7 (16)
Ni1—N2—C2—C1	43.6 (5)	C29—C30—C31—C32	1.1 (16)
N1—C1—C2—N2	−59.5 (6)	C30—C31—C32—C27	−0.5 (15)
C1—N1—C3—C4	55.2 (7)	C28—C27—C32—C31	−1.9 (15)
Ni1—N1—C3—C4	178.4 (4)	C26—C27—C32—C31	177.8 (8)
N1—C3—C4—C5	−133.1 (7)	C33'—O3—C33—N5	1.8 (17)
N1—C3—C4—C9	48.3 (9)	C33'—N5—C33—O3	−1.7 (16)
C9—C4—C5—C6	−0.4 (11)	C34'—N5—C33—O3	166 (2)
C3—C4—C5—C6	−179.1 (7)	C34—N5—C33—O3	0 (3)
C4—C5—C6—C7	−1.3 (13)	C35'—N5—C33—O3	−3 (10)
C5—C6—C7—C8	1.7 (13)	C35—N5—C33—O3	−175.5 (17)
C6—C7—C8—C9	−0.3 (12)	C33—O3—C33'—N5	−1.8 (17)
C5—C4—C9—C8	1.9 (10)	C33—N5—C33'—O3	1.7 (17)
C3—C4—C9—C8	−179.4 (6)	C34'—N5—C33'—O3	−11 (3)
C7—C8—C9—C4	−1.5 (11)	C34—N5—C33'—O3	−177 (2)
C2—N2—C10—C11	−53.8 (7)	C35'—N5—C33'—O3	−179 (2)
Ni1—N2—C10—C11	−176.8 (5)	C35—N5—C33'—O3	30 (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···A	D—H	H···A	D···A	D—H···A
O1—H1C···Cl2	0.85	2.26	3.055 (4)	155
O1—H1D···Cl1ⁱⁱ	0.85	2.24	3.078 (4)	169
O2—H2C···Cl1ⁱⁱ	0.85	2.24	3.071 (4)	168
O2—H2D···Cl2	0.85	2.19	3.041 (4)	174
N1—H1···Cl1ⁱⁱⁱ	0.91	2.54	3.444 (4)	171
N2—H2···O3ⁱ	0.91	2.20	3.102 (8)	169
N3—H3···Cl1	0.91	2.55	3.400 (4)	155
N4—H4···Cl2ⁱⁱ	0.91	2.54	3.428 (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
M_r	719.42
Crystal system, space group	Triclinic, 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)
V (Å³)	1961.8 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.67
Crystal size (mm)	0.42 × 0.40 × 0.35

Data collection
Diffractometer	Siemens SMART 1000 CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.767, 0.800
No. of measured, independent and observed [I > 2σ(I)] reflections	10138, 6781, 4690
R_int	0.018
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.066, 0.201, 1.02
No. of reflections	6781
No. of parameters	450
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	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—O1	2.100 (3)	Ni2—O2	2.111 (3)
Ni1—N1	2.131 (4)	Ni2—N3	2.140 (4)
Ni1—N2	2.143 (4)	Ni2—N4	2.130 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	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.

Acknowledgements

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

References

Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. Google Scholar
Xia, 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
Xia, 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

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.