Bis{2-[2-(1H-indol-3-yl)ethyl­imino­meth­yl]phenolato-κ2N,O}nickel(II) N,N-dimethyl­formamide disolvate

Ali, H.M.; Mohamed Mustafa, M.I.; Rizal, M.R.; Ng, S.W.

doi:10.1107/S1600536808012968

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 6| June 2008| Page m787

doi:10.1107/S1600536808012968

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Bis{2-[2-(1H-indol-3-yl)ethyliminomethyl]phenolato-κ²N,O}nickel(II) N,N-dimethylformamide disolvate

Hapipah M. Ali,^a Mohamed Ibrahim Mohamed Mustafa,^a Mohd. Razali Rizal ^a and Seik Weng Ng ^a ^*

^aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 29 January 2008; accepted 2 May 2008; online 10 May 2008)

The Ni atom in the title compound, [Ni(C₁₇H₁₅N₂O)₂]·2C₃H₇NO, lies on a twofold rotation axis. It is N,O-chelated by the deprotonated Schiff base 2-[2-(1H-indol-3-yl)ethyliminomethyl]phenolate ligand in a square-planar coordination environment. The molecule is linked to a solvent molecule by an indole–dimethylformamide N—H⋯O hydrogen bond.

Related literature

For the structures of Schiff bases derived from the consensation of 2-(indol-3-yl)ethylamine and other substituted salicylaldehydes, see: Ali et al. (2007a ,b ).

Experimental

Crystal data

[Ni(C₁₇H₁₅N₂O)₂]·2C₃H₇NO
M_r = 731.52
Monoclinic, C 2/c
a = 38.927 (2) Å
b = 5.6999 (3) Å
c = 15.7560 (8) Å
β = 98.489 (2)°
V = 3457.6 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.61 mm⁻¹
T = 103 (2) K
0.70 × 0.32 × 0.07 mm

Data collection

Bruker APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.673, T_max = 0.958
7704 measured reflections
3875 independent reflections
2900 reflections with I > 2σ(I)
R_int = 0.030

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.133
S = 1.03
3875 reflections
234 parameters
H-atom parameters constrained
Δρ_max = 2.82 e Å⁻³
Δρ_min = −0.48 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Ni1—O1	1.829 (2)
Ni1—N1	1.922 (2)

O1—Ni1—N1	92.81 (9)
O1—Ni1—N1ⁱ	87.19 (9)
Symmetry code: (i) $[-x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+1]$ .

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3n⋯O2	0.88	1.97	2.811 (3)	159

Data collection: APEX2 (Bruker, 2005 ); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2008 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808012968/sg2223sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808012968/sg2223Isup2.hkl

checkCIF report

Comment top

We have reported a number of metal complexes of Schiff bases derived from the condensation of salicylaldehyde and a biologically active primary amine. The structure of the presence Schiff base, has not been reported, but it is likely to exist as a zwitterion, 2-{[3-(1H-indol-3-yl)-propenyl]ammonio}phenolate as 2-{[3-(1H-Indol-3-yl)-propenyl]methylammonio}phenolate, synthesized from 2-(indol-3-yl)ethylamine and 2-hydroxy-5-methylacetophenone, exists in this form (Ali et al., 2007a, 2007b). The nickel derivative crystallizes from DMF as a disolvate (Scheme I, Fig. 1). The metal atom is N,O-chelated by the deprotonated Schiff base in a square planar coordination enviroment. The molecule is linked to the solvent molecule by an N–H_indole···O_DMF hydrogen bond.

Related literature top

For the structures of Schiff bases derived from the consensation of 2-(indol-3-yl)ethylamine and other substituted salicylaldehydes, see: Ali et al. (2007a,b).

Experimental top

Tryptamine (0.30 g, 1.87 mmol) and salicylaldehyde (0.23 g, 1.86 mmol) were heated in ethanol (50 ml) for an hour. The solvent was removed to give the Schiff base. The ligand (0.49 g, 1.91 mmol) and nickel acetate tetrahydrate (0.23 g, 0.93 mmol) were reacted in ethanol (50 ml); several drops of triethylamine were also added. The solvent was removed and the product was recrystallized from DMF.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2008).

Figures top

Fig. 1. Thermal ellipsoid plot of Ni(C₁₇H₁₄N₂O)₂^.2DMF; displacement ellipsoids are drawn at the 70% probability level, and H atoms are shown as spheres of arbitrary radii. Hydrogen bonds are shown as dashed lines.

Bis{2-[2-(1H-indol-3-yl)ethyliminomethyl]phenolato- κ²N,O}nickel(II) N,N-dimethylformamide disolvate top

Crystal data top

[Ni(C₁₇H₁₄N₂O)₂]·2C₃H₇NO	F(000) = 1544
M_r = 731.52	D_x = 1.405 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2399 reflections
a = 38.927 (2) Å	θ = 2.6–28.5°
b = 5.6999 (3) Å	µ = 0.61 mm⁻¹
c = 15.7560 (8) Å	T = 103 K
β = 98.489 (2)°	Plate, yellow
V = 3457.6 (3) Å³	0.70 × 0.32 × 0.07 mm
Z = 4

Data collection top

Bruker APEXII diffractometer	3875 independent reflections
Radiation source: medium-focus sealed tube	2900 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.030
ϕ and ω scans	θ_max = 27.5°, θ_min = 2.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −48→50
T_min = 0.673, T_max = 0.958	k = −7→5
7704 measured reflections	l = −19→20

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.133	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0586P)² + 9.176P] where P = (F_o² + 2F_c²)/3
3875 reflections	(Δ/σ)_max = 0.001
234 parameters	Δρ_max = 0.82 e Å⁻³
0 restraints	Δρ_min = −0.48 e Å⁻³

Crystal data top

[Ni(C₁₇H₁₄N₂O)₂]·2C₃H₇NO	V = 3457.6 (3) Å³
M_r = 731.52	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 38.927 (2) Å	µ = 0.61 mm⁻¹
b = 5.6999 (3) Å	T = 103 K
c = 15.7560 (8) Å	0.70 × 0.32 × 0.07 mm
β = 98.489 (2)°

Data collection top

Bruker APEXII diffractometer	3875 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2900 reflections with I > 2σ(I)
T_min = 0.673, T_max = 0.958	R_int = 0.030
7704 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.133	H-atom parameters constrained
S = 1.03	Δρ_max = 0.82 e Å⁻³
3875 reflections	Δρ_min = −0.48 e Å⁻³
234 parameters

Special details top

Experimental. A medium-focus collimator of 0.8 mm diameter was used on the diffractometer to measure the somewhat large crystal.

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

	x	y	z	U_iso*/U_eq
Ni1	0.2500	0.7500	0.5000	0.01379 (15)
O1	0.27749 (5)	0.8616 (4)	0.42443 (12)	0.0208 (5)
O2	0.08509 (9)	−0.4015 (5)	0.56375 (17)	0.0564 (9)
N1	0.23434 (6)	0.4881 (4)	0.42765 (14)	0.0151 (5)
N3	0.11380 (6)	−0.0268 (5)	0.48184 (16)	0.0224 (6)
H3N	0.1102	−0.1570	0.5092	0.027*
N4	0.06308 (7)	−0.7205 (4)	0.62051 (16)	0.0215 (5)
C1	0.29181 (7)	0.7412 (5)	0.36804 (16)	0.0169 (5)
C2	0.32195 (8)	0.8312 (5)	0.34033 (17)	0.0199 (6)
H2	0.3311	0.9776	0.3618	0.024*
C3	0.33829 (8)	0.7079 (5)	0.28206 (18)	0.0215 (6)
H3	0.3589	0.7688	0.2650	0.026*
C4	0.32486 (8)	0.4956 (6)	0.24797 (18)	0.0229 (6)
H4	0.3360	0.4139	0.2071	0.027*
C5	0.29539 (8)	0.4055 (5)	0.27382 (17)	0.0202 (6)
H5	0.2860	0.2618	0.2501	0.024*
C6	0.27889 (7)	0.5234 (5)	0.33495 (17)	0.0168 (6)
C7	0.24926 (7)	0.4181 (5)	0.36379 (16)	0.0165 (6)
H7	0.2396	0.2842	0.3332	0.020*
C8	0.20526 (7)	0.3382 (5)	0.44577 (18)	0.0169 (6)
H8A	0.2087	0.2998	0.5077	0.020*
H8B	0.2058	0.1892	0.4137	0.020*
C9	0.16973 (7)	0.4520 (5)	0.42173 (17)	0.0171 (6)
H9A	0.1683	0.5944	0.4570	0.021*
H9B	0.1666	0.4997	0.3607	0.021*
C10	0.14497 (8)	0.0886 (5)	0.48646 (19)	0.0211 (6)
H10	0.1660	0.0388	0.5201	0.025*
C11	0.14169 (7)	0.2850 (5)	0.43600 (17)	0.0175 (6)
C12	0.10598 (7)	0.2930 (5)	0.39755 (17)	0.0175 (6)
C13	0.08600 (8)	0.4471 (6)	0.34154 (18)	0.0229 (7)
H13	0.0964	0.5807	0.3197	0.028*
C14	0.05115 (8)	0.4034 (6)	0.31834 (19)	0.0286 (7)
H14	0.0375	0.5091	0.2808	0.034*
C15	0.03524 (8)	0.2044 (6)	0.3492 (2)	0.0283 (8)
H15	0.0111	0.1779	0.3319	0.034*
C16	0.05416 (8)	0.0488 (6)	0.40391 (19)	0.0249 (7)
H16	0.0435	−0.0851	0.4248	0.030*
C17	0.08943 (8)	0.0937 (5)	0.42782 (17)	0.0192 (6)
C18	0.08801 (10)	−0.5798 (7)	0.6027 (2)	0.0379 (9)
H18	0.1111	−0.6275	0.6237	0.045*
C19	0.02741 (10)	−0.6713 (8)	0.5891 (3)	0.0472 (10)
H19A	0.0258	−0.5257	0.5557	0.071*
H19B	0.0145	−0.6537	0.6376	0.071*
H19C	0.0175	−0.8008	0.5525	0.071*
C20	0.07081 (13)	−0.9334 (7)	0.6694 (3)	0.0521 (11)
H20A	0.0960	−0.9503	0.6844	0.078*
H20B	0.0615	−1.0684	0.6350	0.078*
H20C	0.0602	−0.9258	0.7220	0.078*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.0150 (3)	0.0131 (3)	0.0133 (2)	−0.0029 (2)	0.00219 (17)	−0.0008 (2)
O1	0.0248 (11)	0.0184 (11)	0.0203 (10)	−0.0039 (9)	0.0075 (8)	−0.0011 (9)
O2	0.105 (3)	0.0285 (15)	0.0453 (15)	−0.0269 (16)	0.0436 (16)	−0.0058 (13)
N1	0.0133 (12)	0.0132 (12)	0.0182 (11)	−0.0002 (9)	−0.0001 (9)	0.0026 (9)
N3	0.0214 (13)	0.0202 (13)	0.0256 (13)	−0.0042 (11)	0.0038 (10)	0.0072 (11)
N4	0.0240 (13)	0.0171 (13)	0.0244 (12)	−0.0027 (11)	0.0074 (10)	0.0012 (10)
C1	0.0200 (14)	0.0164 (13)	0.0135 (12)	0.0025 (13)	−0.0003 (10)	0.0036 (12)
C2	0.0231 (15)	0.0189 (14)	0.0174 (13)	−0.0020 (12)	0.0025 (11)	0.0020 (11)
C3	0.0193 (14)	0.0256 (17)	0.0199 (13)	0.0008 (12)	0.0042 (11)	0.0095 (12)
C4	0.0265 (16)	0.0245 (16)	0.0186 (13)	0.0070 (13)	0.0063 (12)	0.0017 (12)
C5	0.0252 (16)	0.0189 (15)	0.0163 (13)	0.0008 (12)	0.0025 (11)	−0.0004 (11)
C6	0.0179 (14)	0.0167 (14)	0.0154 (12)	0.0020 (12)	0.0015 (10)	0.0022 (11)
C7	0.0180 (14)	0.0171 (14)	0.0128 (12)	0.0009 (11)	−0.0027 (10)	0.0005 (11)
C8	0.0168 (14)	0.0147 (13)	0.0191 (13)	−0.0041 (11)	0.0023 (11)	−0.0006 (11)
C9	0.0178 (14)	0.0170 (14)	0.0163 (13)	−0.0013 (12)	0.0019 (10)	0.0017 (11)
C10	0.0183 (15)	0.0207 (15)	0.0242 (14)	−0.0010 (12)	0.0027 (11)	0.0032 (12)
C11	0.0192 (14)	0.0176 (15)	0.0161 (12)	−0.0006 (11)	0.0039 (10)	−0.0022 (11)
C12	0.0204 (14)	0.0193 (15)	0.0136 (12)	−0.0013 (11)	0.0052 (10)	−0.0027 (11)
C13	0.0233 (16)	0.0268 (17)	0.0184 (14)	0.0003 (13)	0.0020 (12)	0.0017 (12)
C14	0.0201 (16)	0.042 (2)	0.0217 (14)	0.0034 (14)	−0.0018 (12)	0.0025 (14)
C15	0.0197 (15)	0.040 (2)	0.0250 (15)	−0.0045 (14)	0.0029 (12)	−0.0057 (14)
C16	0.0205 (16)	0.0300 (18)	0.0255 (15)	−0.0066 (13)	0.0074 (12)	−0.0040 (13)
C17	0.0198 (15)	0.0189 (15)	0.0195 (13)	−0.0034 (12)	0.0050 (11)	−0.0020 (12)
C18	0.043 (2)	0.037 (2)	0.0393 (19)	−0.0171 (17)	0.0231 (16)	−0.0175 (17)
C19	0.029 (2)	0.064 (3)	0.047 (2)	−0.0047 (19)	0.0017 (17)	−0.010 (2)
C20	0.081 (3)	0.032 (2)	0.045 (2)	0.012 (2)	0.016 (2)	0.0071 (19)

Geometric parameters (Å, º) top

Ni1—O1ⁱ	1.829 (2)	C8—C9	1.524 (4)
Ni1—O1	1.829 (2)	C8—H8A	0.9900
Ni1—N1ⁱ	1.922 (2)	C8—H8B	0.9900
Ni1—N1	1.922 (2)	C9—C11	1.490 (4)
O1—C1	1.310 (3)	C9—H9A	0.9900
O2—C18	1.184 (5)	C9—H9B	0.9900
N1—C7	1.297 (3)	C10—C11	1.368 (4)
N1—C8	1.479 (3)	C10—H10	0.9500
N3—C17	1.363 (4)	C11—C12	1.433 (4)
N3—C10	1.373 (4)	C12—C13	1.397 (4)
N3—H3N	0.8800	C12—C17	1.423 (4)
N4—C18	1.320 (4)	C13—C14	1.375 (4)
N4—C19	1.431 (4)	C13—H13	0.9500
N4—C20	1.445 (4)	C14—C15	1.412 (5)
C1—C2	1.408 (4)	C14—H14	0.9500
C1—C6	1.410 (4)	C15—C16	1.373 (5)
C2—C3	1.383 (4)	C15—H15	0.9500
C2—H2	0.9500	C16—C17	1.393 (4)
C3—C4	1.394 (4)	C16—H16	0.9500
C3—H3	0.9500	C18—H18	0.9500
C4—C5	1.372 (4)	C19—H19A	0.9800
C4—H4	0.9500	C19—H19B	0.9800
C5—C6	1.405 (4)	C19—H19C	0.9800
C5—H5	0.9500	C20—H20A	0.9800
C6—C7	1.432 (4)	C20—H20B	0.9800
C7—H7	0.9500	C20—H20C	0.9800

O1ⁱ—Ni1—O1	180.00 (10)	C11—C9—H9A	109.6
O1ⁱ—Ni1—N1ⁱ	92.81 (9)	C8—C9—H9A	109.6
O1—Ni1—N1ⁱ	87.19 (9)	C11—C9—H9B	109.6
O1ⁱ—Ni1—N1	87.19 (9)	C8—C9—H9B	109.6
O1—Ni1—N1	92.81 (9)	H9A—C9—H9B	108.1
N1ⁱ—Ni1—N1	180.000 (1)	C11—C10—N3	110.8 (3)
C1—O1—Ni1	127.41 (19)	C11—C10—H10	124.6
C7—N1—C8	114.6 (2)	N3—C10—H10	124.6
C7—N1—Ni1	124.0 (2)	C10—C11—C12	105.9 (2)
C8—N1—Ni1	121.26 (17)	C10—C11—C9	127.1 (3)
C17—N3—C10	108.6 (2)	C12—C11—C9	127.0 (2)
C17—N3—H3N	125.7	C13—C12—C17	118.4 (3)
C10—N3—H3N	125.7	C13—C12—C11	134.6 (3)
C18—N4—C19	120.9 (3)	C17—C12—C11	107.0 (2)
C18—N4—C20	121.4 (3)	C14—C13—C12	119.3 (3)
C19—N4—C20	117.6 (3)	C14—C13—H13	120.3
O1—C1—C2	118.5 (3)	C12—C13—H13	120.3
O1—C1—C6	123.2 (2)	C13—C14—C15	121.3 (3)
C2—C1—C6	118.3 (3)	C13—C14—H14	119.3
C3—C2—C1	120.4 (3)	C15—C14—H14	119.3
C3—C2—H2	119.8	C16—C15—C14	120.9 (3)
C1—C2—H2	119.8	C16—C15—H15	119.6
C2—C3—C4	120.9 (3)	C14—C15—H15	119.6
C2—C3—H3	119.5	C15—C16—C17	117.9 (3)
C4—C3—H3	119.5	C15—C16—H16	121.1
C5—C4—C3	119.5 (3)	C17—C16—H16	121.1
C5—C4—H4	120.2	N3—C17—C16	130.1 (3)
C3—C4—H4	120.2	N3—C17—C12	107.7 (3)
C4—C5—C6	120.7 (3)	C16—C17—C12	122.2 (3)
C4—C5—H5	119.6	O2—C18—N4	127.9 (4)
C6—C5—H5	119.6	O2—C18—H18	116.1
C5—C6—C1	120.0 (3)	N4—C18—H18	116.1
C5—C6—C7	119.2 (3)	N4—C19—H19A	109.5
C1—C6—C7	120.8 (2)	N4—C19—H19B	109.5
N1—C7—C6	126.2 (3)	H19A—C19—H19B	109.5
N1—C7—H7	116.9	N4—C19—H19C	109.5
C6—C7—H7	116.9	H19A—C19—H19C	109.5
N1—C8—C9	113.5 (2)	H19B—C19—H19C	109.5
N1—C8—H8A	108.9	N4—C20—H20A	109.5
C9—C8—H8A	108.9	N4—C20—H20B	109.5
N1—C8—H8B	108.9	H20A—C20—H20B	109.5
C9—C8—H8B	108.9	N4—C20—H20C	109.5
H8A—C8—H8B	107.7	H20A—C20—H20C	109.5
C11—C9—C8	110.4 (2)	H20B—C20—H20C	109.5

N1ⁱ—Ni1—O1—C1	153.4 (2)	N1—C8—C9—C11	176.0 (2)
N1—Ni1—O1—C1	−26.6 (2)	C17—N3—C10—C11	0.0 (3)
O1ⁱ—Ni1—N1—C7	−164.6 (2)	N3—C10—C11—C12	0.2 (3)
O1—Ni1—N1—C7	15.4 (2)	N3—C10—C11—C9	−178.0 (3)
O1ⁱ—Ni1—N1—C8	10.6 (2)	C8—C9—C11—C10	19.2 (4)
O1—Ni1—N1—C8	−169.4 (2)	C8—C9—C11—C12	−158.7 (3)
Ni1—O1—C1—C2	−155.2 (2)	C10—C11—C12—C13	179.0 (3)
Ni1—O1—C1—C6	23.5 (4)	C9—C11—C12—C13	−2.8 (5)
O1—C1—C2—C3	178.8 (3)	C10—C11—C12—C17	−0.3 (3)
C6—C1—C2—C3	0.0 (4)	C9—C11—C12—C17	177.9 (3)
C1—C2—C3—C4	1.6 (4)	C17—C12—C13—C14	0.8 (4)
C2—C3—C4—C5	−1.3 (4)	C11—C12—C13—C14	−178.5 (3)
C3—C4—C5—C6	−0.8 (4)	C12—C13—C14—C15	−0.7 (5)
C4—C5—C6—C1	2.4 (4)	C13—C14—C15—C16	0.4 (5)
C4—C5—C6—C7	−176.7 (3)	C14—C15—C16—C17	0.0 (4)
O1—C1—C6—C5	179.3 (3)	C10—N3—C17—C16	−178.7 (3)
C2—C1—C6—C5	−2.0 (4)	C10—N3—C17—C12	−0.2 (3)
O1—C1—C6—C7	−1.6 (4)	C15—C16—C17—N3	178.4 (3)
C2—C1—C6—C7	177.1 (3)	C15—C16—C17—C12	0.1 (4)
C8—N1—C7—C6	−177.0 (3)	C13—C12—C17—N3	−179.1 (2)
Ni1—N1—C7—C6	−1.5 (4)	C11—C12—C17—N3	0.3 (3)
C5—C6—C7—N1	169.8 (3)	C13—C12—C17—C16	−0.4 (4)
C1—C6—C7—N1	−9.3 (4)	C11—C12—C17—C16	179.0 (3)
C7—N1—C8—C9	−108.6 (3)	C19—N4—C18—O2	2.6 (5)
Ni1—N1—C8—C9	75.7 (3)	C20—N4—C18—O2	−179.7 (3)

Symmetry code: (i) −x+1/2, −y+3/2, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3N···O2	0.88	1.97	2.811 (3)	159

Experimental details

Crystal data
Chemical formula	[Ni(C₁₇H₁₄N₂O)₂]·2C₃H₇NO
M_r	731.52
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	103
a, b, c (Å)	38.927 (2), 5.6999 (3), 15.7560 (8)
β (°)	98.489 (2)
V (Å³)	3457.6 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.61
Crystal size (mm)	0.70 × 0.32 × 0.07

Data collection
Diffractometer	Bruker APEXII diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.673, 0.958
No. of measured, independent and observed [I > 2σ(I)] reflections	7704, 3875, 2900
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.133, 1.03
No. of reflections	3875
No. of parameters	234
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.82, −0.48

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2008).

Selected bond lengths (Å) top

Ni1—O1

1.829 (2)

Ni1—N1

1.922 (2)

Acknowledgements

The authors thank the University of Canterbury, New Zealand, for the diffraction measurements, and the Science Fund (12–02-03–2031) for supporting this study.

References

Ali, H. M., Emmy Maryati, O. & Ng, S. W. (2007a). Acta Cryst. E63, o3458. Web of Science CSD CrossRef IUCr Journals Google Scholar
Ali, H. M., Zuraini, K., Wan Jefrey, B. & Ng, S. W. (2007b). Acta Cryst. E63, o1729–o1730. Web of Science CSD CrossRef IUCr Journals Google Scholar
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Bruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
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
Westrip, S. P. (2008). publCIF. In preparation. Google Scholar

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