Bis(1,10-phenanthroline-κ2N,N′)(sulfato-κ2O,O′)nickel(II) propane-1,3-diol solvate

Ni, C.; Zhong, K.-L.; Cui, J.-D.

doi:10.1107/S1600536810020210

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 7| July 2010| Pages m746-m747

doi:10.1107/S1600536810020210

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Bis(1,10-phenanthroline-κ²N,N′)(sulfato-κ²O,O′)nickel(II) propane-1,3-diol solvate

Chao Ni,^a ^* Kai-Long Zhong ^a and Jiang-Dong Cui ^a

^aDepartment of Applied Chemistry, Nanjing College of Chemical Technology, Nanjing 210048, People's Republic of China
^*Correspondence e-mail: nichao@njcc.edu.cn

(Received 10 May 2010; accepted 28 May 2010; online 5 June 2010)

In the structure of the title compound, [Ni(SO₄)(C₁₂H₈N₂)₂]·C₃H₈O₂, the Ni^II ion (site symmetry 2) is six-coordinated in a distorted octahedral manner by four N atoms from two chelating 1,10-phenanthroline (phen) ligands and two O atoms from a bidentate sulfate ligand (2 symmetry). The dihedral angle between the two chelating NCCN groups is 80.9 (1)°. The central C atom of the propane-1,3-diol solvent molecule is likewise located on a twofold rotation axis. In the crystal structure, the [Ni(SO₄)(C₁₂H₈N₂)₂] and C₃H₈O₂ entities are connected through intermolecular O—H⋯O hydrogen bonding.

Related literature

For the isotypic Zn and Co structures, see: Cui et al. (2010 ) and Zhong (2010 ), respectively. For the ethane-1,2-diol solvate of the title complex, see: Zhong et al. (2009 ). For background to coordination polymers constructed from N-containing ligands, see: Zhang et al. (1999 ); Blake et al. (2007 ); Wang et al. (2007 ).

Experimental

Crystal data

[Ni(SO₄)(C₁₂H₈N₂)₂]·C₃H₈O₂
M_r = 591.26
Monoclinic, C 2/c
a = 18.243 (4) Å
b = 12.440 (3) Å
c = 13.180 (3) Å
β = 121.58 (3)°
V = 2548.2 (13) Å³
Z = 4
Mo Kα radiation
μ = 0.90 mm⁻¹
T = 223 K
0.55 × 0.50 × 0.40 mm

Data collection

Rigaku Mercury CCD diffractometer
Absorption correction: multi-scan (REQAB: Jacobson, 1998 ) T_min = 0.750, T_max = 1.000
7078 measured reflections
2877 independent reflections
2630 reflections with I > 2σ(I)
R_int = 0.017

Refinement

R[F² > 2σ(F²)] = 0.034
wR(F²) = 0.093
S = 1.05
2877 reflections
179 parameters
H-atom parameters constrained
Δρ_max = 0.79 e Å⁻³
Δρ_min = −0.42 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Ni1—N2	2.0775 (16)
Ni1—N1	2.0802 (16)
Ni1—O1	2.1127 (14)
S1—O2	1.4559 (14)
S1—O1	1.4950 (14)

N2—Ni1—N1	80.05 (6)
O1ⁱ—Ni1—O1	67.73 (7)
Symmetry code: (i) $[-x+1, y, -z+{\script{1\over 2}}]$ .

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O2	0.82	1.92	2.743 (2)	179

Data collection: CrystalClear (Rigaku, 2007 ); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810020210/wm2347sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810020210/wm2347Isup2.hkl

checkCIF report

Comment top

Many N containing ligands, such as 1,10-phenanthroline, 4,4'-bipyridine and 2,2'-bipyridine have been widely applied in constructing coordination polymers as auxiliary ligands (Zhang et al., 1999; Blake et al., 2007; Wang et al., 2007). The title nickel compound, [NiSO₄(C₁₂H₈N₂)₂]^.C₃H₈O₂, (I), was obtained unintentionally during an attempt to synthesize coordination polymers of Ni^II with 1,10-phenanthroline as second ligand via a solvothermal reaction. (I) is isotypic with the recently reported cobalt(II) and zinc(II) structures [Zhong 2010, (II); Cui et al., 2010, (III)].

The metal complex and solvent entities of (I) are held together by two intermolecular O—H···O hydrogen bonds including the uncoordinated O atoms of the sulfate group (Fig. 1). In the complex molecule, the Ni^II atom is six-coordinated in a distorted octahedral manner by four N atoms from two chelating 1,10-phenanthroline (phen) ligands and two O atoms from a bidentate-chelating sulfate anion. The Ni—O bond length [2.1127 (14) Å], the O—Ni—O bite angle [67.73 (7)°], the Ni—N bond lengths [2.0775 (16) and 2.0802 (16) Å], and the N—Ni—N bite angle [80.05 (6)°] are in good agreement with those of the observed in the ethane-1,2-diol solvate [NiSO₄(C₁₂H₈N₂)₂]^.C₂H₆O₂, (IV), [2.1077 (16) Å, 67.58 (8)°, 2.0774 (18), 2.0805 (15)Å and 79.99 (7)°, respectively; Zhong et al., 2009]. The two chelating NCCN groups have a dihedral angle of 80.9 (1)°, which is much larger than that found in the structure of (IV), 71.0°. The Ni^II, the S and the central C atom of the propane-1,3-diol solvent molecule lie on a twofold rotation axis. Selected bond lengths and angles are compiled in Table 1 and intermolecular hydrogen bonding in Table 2, respectively.

In the title complex, the geometry of the phen and sulfate ligands is in good agreement with those of the previously reported metal complexes, (II), (III) and (IV). The phen ligands are all planar with the largest deviation of atoms from their mean plane less than 0.03 Å. The bond distances and angles in phen [1.353 (3)-1.436 (2) Å and 116.97 (17)-123.95 (17)° Å, respectivly] are all normal. The S—O distances within the sulfate ligands, 1.4559 (14) Å for and 1.4950 (14) Å are also similar to those observed for (II), (III) and (VI).

Related literature top

For the isotypic Zn and Co structures, see: Cui et al. (2010) and Zhong (2010), respectively. For the ethane-1,2-diol solvate of the title complex, see: Zhong et al. (2009). For background to coordination polymers constructed from N-containing ligands, see: Zhang et al. (1999); Blake et al. (2007); Wang et al. (2007).

Experimental top

0.2 mmol phen, 0.1 mmol melamine, 0.1 mmol NiSO₄^.7H₂O, 2.0 ml propane-1,3-diol and 1.0 ml water were mixed and placed in a thick Pyrex tube, which was sealed and heated to 413 K for 96 h. Blue block-shaped crystals of (I) were obtained after the reaction time.

Computing details top

Data collection: CrystalClear (Rigaku, 2007); cell refinement: CrystalClear (Rigaku, 2007); data reduction: CrystalClear (Rigaku, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. The dashed lines represent O—H···O interactions. Unlabeled atoms are related to the labelled atoms by the symmetry operator (-x+1, y, -z+1/2).

Bis(1,10-phenanthroline-κ²N,N')(sulfato- κ²O,O')nickel(II) propane-1,3-diol solvate top

Crystal data top

[Ni(SO₄)(C₁₂H₈N₂)₂]·C₃H₈O₂	F(000) = 1224
M_r = 591.26	D_x = 1.541 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 6113 reflections
a = 18.243 (4) Å	θ = 3.2–27.5°
b = 12.440 (3) Å	µ = 0.90 mm⁻¹
c = 13.180 (3) Å	T = 223 K
β = 121.58 (3)°	Block, blue
V = 2548.2 (13) Å³	0.55 × 0.50 × 0.40 mm
Z = 4

Data collection top

Rigaku Mercury CCD diffractometer	2877 independent reflections
Radiation source: fine-focus sealed tube	2630 reflections with I > 2σ(I)
Graphite Monochromator monochromator	R_int = 0.017
Detector resolution: 28.5714 pixels mm^-1	θ_max = 27.5°, θ_min = 3.2°
ω scans	h = −23→23
Absorption correction: multi-scan (REQAB: Jacobson, 1998)	k = −16→13
T_min = 0.750, T_max = 1.000	l = −16→17
7078 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.034	H-atom parameters constrained
wR(F²) = 0.093	w = 1/[σ²(F_o²) + (0.0574P)² + 1.7246P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
2877 reflections	Δρ_max = 0.79 e Å⁻³
179 parameters	Δρ_min = −0.42 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0115 (8)

Crystal data top

[Ni(SO₄)(C₁₂H₈N₂)₂]·C₃H₈O₂	V = 2548.2 (13) Å³
M_r = 591.26	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 18.243 (4) Å	µ = 0.90 mm⁻¹
b = 12.440 (3) Å	T = 223 K
c = 13.180 (3) Å	0.55 × 0.50 × 0.40 mm
β = 121.58 (3)°

Data collection top

Rigaku Mercury CCD diffractometer	2877 independent reflections
Absorption correction: multi-scan (REQAB: Jacobson, 1998)	2630 reflections with I > 2σ(I)
T_min = 0.750, T_max = 1.000	R_int = 0.017
7078 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	0 restraints
wR(F²) = 0.093	H-atom parameters constrained
S = 1.05	Δρ_max = 0.79 e Å⁻³
2877 reflections	Δρ_min = −0.42 e Å⁻³
179 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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

	x	y	z	U_iso*/U_eq
Ni1	0.5000	0.31623 (2)	0.2500	0.02219 (13)
S1	0.5000	0.53132 (5)	0.2500	0.02350 (16)
O1	0.44210 (8)	0.45725 (10)	0.15044 (11)	0.0300 (3)
O2	0.44999 (10)	0.59777 (13)	0.28297 (15)	0.0422 (4)
N1	0.40871 (10)	0.20994 (12)	0.12675 (13)	0.0245 (3)
N2	0.41995 (10)	0.30246 (12)	0.31754 (14)	0.0252 (3)
C2	0.33170 (14)	0.10453 (17)	−0.05175 (18)	0.0351 (4)
H2A	0.3282	0.0788	−0.1204	0.042*
C6	0.22391 (12)	0.13600 (17)	0.21208 (18)	0.0345 (4)
H6A	0.1843	0.1178	0.2334	0.041*
C7	0.29358 (12)	0.20714 (16)	0.28623 (17)	0.0289 (4)
C9	0.37020 (14)	0.32691 (16)	0.45183 (18)	0.0354 (4)
H9A	0.3774	0.3602	0.5197	0.043*
C5	0.21523 (12)	0.09508 (16)	0.11125 (18)	0.0338 (4)
H5A	0.1685	0.0509	0.0630	0.041*
C4	0.27619 (11)	0.11813 (14)	0.07706 (16)	0.0275 (4)
C10	0.42736 (12)	0.34793 (16)	0.41402 (17)	0.0303 (4)
H10A	0.4725	0.3956	0.4580	0.036*
C8	0.30380 (13)	0.25725 (17)	0.38851 (17)	0.0356 (4)
H8A	0.2653	0.2429	0.4129	0.043*
C1	0.40052 (13)	0.17061 (15)	0.02734 (17)	0.0305 (4)
H1A	0.4422	0.1877	0.0096	0.037*
C11	0.35423 (11)	0.23219 (13)	0.25508 (15)	0.0239 (3)
C3	0.26998 (13)	0.07832 (15)	−0.02736 (17)	0.0325 (4)
H3A	0.2241	0.0345	−0.0792	0.039*
C12	0.34677 (11)	0.18502 (13)	0.15061 (16)	0.0233 (3)
C14	0.4235 (2)	0.8716 (3)	0.2220 (3)	0.0797 (10)
H14A	0.3738	0.9177	0.1952	0.096*
H14B	0.4111	0.8230	0.1574	0.096*
C13	0.5000	0.9397 (3)	0.2500	0.0588 (10)
O3	0.43615 (17)	0.81214 (15)	0.3188 (2)	0.0711 (7)
H3	0.4403	0.7483	0.3072	0.107*
H13	0.5146	0.9859	0.3169	0.085*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.02047 (18)	0.01993 (18)	0.02456 (19)	0.000	0.01067 (14)	0.000
S1	0.0196 (3)	0.0197 (3)	0.0300 (3)	0.000	0.0122 (2)	0.000
O1	0.0245 (6)	0.0261 (6)	0.0273 (7)	−0.0002 (5)	0.0052 (5)	0.0017 (5)
O2	0.0377 (8)	0.0369 (8)	0.0568 (10)	0.0089 (6)	0.0281 (8)	−0.0045 (7)
N1	0.0259 (7)	0.0216 (7)	0.0257 (7)	−0.0002 (6)	0.0132 (6)	−0.0002 (6)
N2	0.0236 (7)	0.0236 (7)	0.0268 (7)	0.0003 (6)	0.0120 (6)	−0.0008 (6)
C2	0.0418 (11)	0.0340 (10)	0.0274 (9)	−0.0021 (9)	0.0167 (9)	−0.0068 (8)
C6	0.0268 (9)	0.0398 (11)	0.0372 (10)	−0.0050 (8)	0.0170 (8)	0.0041 (9)
C7	0.0250 (8)	0.0324 (9)	0.0285 (9)	0.0016 (7)	0.0134 (8)	0.0045 (7)
C9	0.0417 (11)	0.0384 (11)	0.0291 (9)	0.0038 (9)	0.0205 (9)	−0.0027 (8)
C5	0.0251 (9)	0.0339 (10)	0.0342 (10)	−0.0075 (8)	0.0099 (8)	−0.0005 (8)
C4	0.0251 (8)	0.0243 (8)	0.0262 (8)	−0.0013 (7)	0.0086 (7)	0.0017 (7)
C10	0.0307 (9)	0.0288 (9)	0.0279 (9)	0.0002 (7)	0.0129 (8)	−0.0044 (7)
C8	0.0343 (10)	0.0455 (12)	0.0333 (10)	0.0005 (9)	0.0221 (9)	0.0024 (9)
C1	0.0343 (10)	0.0290 (9)	0.0304 (9)	−0.0015 (8)	0.0186 (8)	−0.0019 (7)
C11	0.0216 (8)	0.0223 (8)	0.0238 (8)	0.0016 (6)	0.0092 (7)	0.0024 (7)
C3	0.0321 (10)	0.0280 (9)	0.0276 (9)	−0.0054 (7)	0.0089 (8)	−0.0050 (7)
C12	0.0222 (8)	0.0202 (8)	0.0243 (8)	0.0004 (6)	0.0100 (7)	0.0023 (6)
C14	0.077 (2)	0.081 (2)	0.080 (2)	0.0248 (19)	0.0404 (19)	0.0057 (19)
C13	0.091 (3)	0.0280 (15)	0.070 (2)	0.000	0.051 (2)	0.000
O3	0.1204 (19)	0.0423 (10)	0.0973 (16)	0.0019 (10)	0.0895 (16)	−0.0033 (10)

Geometric parameters (Å, º) top

Ni1—N2ⁱ	2.0775 (16)	C7—C11	1.402 (3)
Ni1—N2	2.0775 (16)	C7—C8	1.406 (3)
Ni1—N1	2.0802 (16)	C9—C8	1.362 (3)
Ni1—N1ⁱ	2.0802 (16)	C9—C10	1.396 (3)
Ni1—O1ⁱ	2.1127 (14)	C9—H9A	0.9300
Ni1—O1	2.1127 (14)	C5—C4	1.431 (3)
Ni1—S1	2.6758 (9)	C5—H5A	0.9300
S1—O2ⁱ	1.4559 (14)	C4—C12	1.408 (2)
S1—O2	1.4559 (14)	C4—C3	1.410 (3)
S1—O1	1.4950 (14)	C10—H10A	0.9300
S1—O1ⁱ	1.4950 (14)	C8—H8A	0.9300
N1—C1	1.332 (2)	C1—H1A	0.9300
N1—C12	1.358 (2)	C11—C12	1.436 (2)
N2—C10	1.332 (2)	C3—H3A	0.9300
N2—C11	1.359 (2)	C14—O3	1.384 (4)
C2—C3	1.362 (3)	C14—C13	1.505 (4)
C2—C1	1.403 (3)	C14—H14A	0.9700
C2—H2A	0.9300	C14—H14B	0.9700
C6—C5	1.353 (3)	C13—C14ⁱ	1.505 (4)
C6—C7	1.433 (3)	C13—H13	0.9659
C6—H6A	0.9300	O3—H3	0.8200

N2ⁱ—Ni1—N2	170.54 (8)	C5—C6—H6A	119.7
N2ⁱ—Ni1—N1	93.90 (6)	C7—C6—H6A	119.7
N2—Ni1—N1	80.05 (6)	C11—C7—C8	116.97 (17)
N2ⁱ—Ni1—N1ⁱ	80.05 (6)	C11—C7—C6	119.45 (18)
N2—Ni1—N1ⁱ	93.90 (6)	C8—C7—C6	123.55 (18)
N1—Ni1—N1ⁱ	101.07 (9)	C8—C9—C10	119.43 (18)
N2ⁱ—Ni1—O1ⁱ	95.71 (6)	C8—C9—H9A	120.3
N2—Ni1—O1ⁱ	92.14 (6)	C10—C9—H9A	120.3
N1—Ni1—O1ⁱ	161.48 (5)	C6—C5—C4	121.57 (18)
N1ⁱ—Ni1—O1ⁱ	96.16 (6)	C6—C5—H5A	119.2
N2ⁱ—Ni1—O1	92.14 (6)	C4—C5—H5A	119.2
N2—Ni1—O1	95.71 (6)	C12—C4—C3	117.17 (17)
N1—Ni1—O1	96.16 (6)	C12—C4—C5	118.88 (17)
N1ⁱ—Ni1—O1	161.48 (5)	C3—C4—C5	123.95 (17)
O1ⁱ—Ni1—O1	67.73 (7)	N2—C10—C9	122.67 (18)
N2ⁱ—Ni1—S1	94.73 (4)	N2—C10—H10A	118.7
N2—Ni1—S1	94.73 (4)	C9—C10—H10A	118.7
N1—Ni1—S1	129.47 (4)	C9—C8—C7	119.88 (18)
N1ⁱ—Ni1—S1	129.47 (4)	C9—C8—H8A	120.1
O1ⁱ—Ni1—S1	33.86 (4)	C7—C8—H8A	120.1
O1—Ni1—S1	33.86 (4)	N1—C1—C2	122.82 (18)
O2ⁱ—S1—O2	110.81 (14)	N1—C1—H1A	118.6
O2ⁱ—S1—O1	110.68 (9)	C2—C1—H1A	118.6
O2—S1—O1	110.29 (8)	N2—C11—C7	123.16 (16)
O2ⁱ—S1—O1ⁱ	110.29 (8)	N2—C11—C12	117.02 (15)
O2—S1—O1ⁱ	110.68 (9)	C7—C11—C12	119.80 (16)
O1—S1—O1ⁱ	103.90 (11)	C2—C3—C4	119.49 (18)
O2ⁱ—S1—Ni1	124.60 (7)	C2—C3—H3A	120.3
O2—S1—Ni1	124.60 (7)	C4—C3—H3A	120.3
O1—S1—Ni1	51.95 (5)	N1—C12—C4	123.17 (17)
O1ⁱ—S1—Ni1	51.95 (5)	N1—C12—C11	117.15 (15)
S1—O1—Ni1	94.19 (7)	C4—C12—C11	119.66 (16)
C1—N1—C12	117.76 (16)	O3—C14—C13	112.9 (3)
C1—N1—Ni1	129.29 (13)	O3—C14—H14A	109.0
C12—N1—Ni1	112.78 (12)	C13—C14—H14A	109.0
C10—N2—C11	117.89 (16)	O3—C14—H14B	109.0
C10—N2—Ni1	129.14 (13)	C13—C14—H14B	109.0
C11—N2—Ni1	112.88 (12)	H14A—C14—H14B	107.8
C3—C2—C1	119.57 (18)	C14—C13—C14ⁱ	111.4 (3)
C3—C2—H2A	120.2	C14—O3—H3	109.5
C1—C2—H2A	120.2	C14—O3—H13	51.3
C5—C6—C7	120.55 (18)	H3—O3—H13	134.4

N2ⁱ—Ni1—S1—O2ⁱ	−3.49 (9)	O1—Ni1—N2—C10	−85.94 (16)
N2—Ni1—S1—O2ⁱ	176.51 (9)	S1—Ni1—N2—C10	−51.94 (16)
N1—Ni1—S1—O2ⁱ	−102.49 (10)	N1—Ni1—N2—C11	2.48 (12)
N1ⁱ—Ni1—S1—O2ⁱ	77.51 (10)	N1ⁱ—Ni1—N2—C11	−98.09 (12)
O1ⁱ—Ni1—S1—O2ⁱ	89.72 (10)	O1ⁱ—Ni1—N2—C11	165.58 (12)
O1—Ni1—S1—O2ⁱ	−90.28 (10)	O1—Ni1—N2—C11	97.75 (12)
N2ⁱ—Ni1—S1—O2	176.51 (9)	S1—Ni1—N2—C11	131.75 (11)
N2—Ni1—S1—O2	−3.49 (9)	C5—C6—C7—C11	−1.5 (3)
N1—Ni1—S1—O2	77.51 (10)	C5—C6—C7—C8	176.34 (19)
N1ⁱ—Ni1—S1—O2	−102.49 (10)	C7—C6—C5—C4	2.1 (3)
O1ⁱ—Ni1—S1—O2	−90.28 (10)	C6—C5—C4—C12	0.0 (3)
O1—Ni1—S1—O2	89.72 (10)	C6—C5—C4—C3	−179.52 (19)
N2ⁱ—Ni1—S1—O1	86.79 (8)	C11—N2—C10—C9	−0.7 (3)
N2—Ni1—S1—O1	−93.21 (8)	Ni1—N2—C10—C9	−176.81 (14)
N1—Ni1—S1—O1	−12.21 (8)	C8—C9—C10—N2	0.0 (3)
N1ⁱ—Ni1—S1—O1	167.79 (8)	C10—C9—C8—C7	0.1 (3)
O1ⁱ—Ni1—S1—O1	180.0	C11—C7—C8—C9	0.3 (3)
N2ⁱ—Ni1—S1—O1ⁱ	−93.21 (8)	C6—C7—C8—C9	−177.63 (19)
N2—Ni1—S1—O1ⁱ	86.79 (8)	C12—N1—C1—C2	−0.6 (3)
N1—Ni1—S1—O1ⁱ	167.79 (8)	Ni1—N1—C1—C2	−175.62 (14)
N1ⁱ—Ni1—S1—O1ⁱ	−12.21 (8)	C3—C2—C1—N1	−0.1 (3)
O1—Ni1—S1—O1ⁱ	180.0	C10—N2—C11—C7	1.2 (3)
O2ⁱ—S1—O1—Ni1	118.37 (8)	Ni1—N2—C11—C7	177.92 (13)
O2—S1—O1—Ni1	−118.64 (8)	C10—N2—C11—C12	179.30 (15)
O1ⁱ—S1—O1—Ni1	0.0	Ni1—N2—C11—C12	−3.94 (19)
N2ⁱ—Ni1—O1—S1	−95.30 (7)	C8—C7—C11—N2	−1.0 (3)
N2—Ni1—O1—S1	89.97 (7)	C6—C7—C11—N2	177.04 (17)
N1—Ni1—O1—S1	170.54 (6)	C8—C7—C11—C12	−179.08 (16)
N1ⁱ—Ni1—O1—S1	−31.0 (2)	C6—C7—C11—C12	−1.1 (3)
O1ⁱ—Ni1—O1—S1	0.0	C1—C2—C3—C4	0.0 (3)
N2ⁱ—Ni1—N1—C1	−12.76 (16)	C12—C4—C3—C2	0.8 (3)
N2—Ni1—N1—C1	174.57 (17)	C5—C4—C3—C2	−179.67 (19)
N1ⁱ—Ni1—N1—C1	−93.37 (16)	C1—N1—C12—C4	1.5 (3)
O1ⁱ—Ni1—N1—C1	108.4 (2)	Ni1—N1—C12—C4	177.32 (13)
O1—Ni1—N1—C1	79.82 (16)	C1—N1—C12—C11	−177.07 (16)
S1—Ni1—N1—C1	86.63 (16)	Ni1—N1—C12—C11	−1.27 (18)
N2ⁱ—Ni1—N1—C12	172.05 (12)	C3—C4—C12—N1	−1.6 (3)
N2—Ni1—N1—C12	−0.63 (11)	C5—C4—C12—N1	178.81 (16)
N1ⁱ—Ni1—N1—C12	91.44 (12)	C3—C4—C12—C11	176.96 (16)
O1ⁱ—Ni1—N1—C12	−66.8 (2)	C5—C4—C12—C11	−2.6 (2)
O1—Ni1—N1—C12	−95.37 (12)	N2—C11—C12—N1	3.6 (2)
S1—Ni1—N1—C12	−88.56 (12)	C7—C11—C12—N1	−178.23 (15)
N1—Ni1—N2—C10	178.78 (17)	N2—C11—C12—C4	−175.08 (15)
N1ⁱ—Ni1—N2—C10	78.21 (16)	C7—C11—C12—C4	3.1 (2)
O1ⁱ—Ni1—N2—C10	−18.11 (16)	O3—C14—C13—C14ⁱ	65.6 (2)

Symmetry code: (i) −x+1, y, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O2	0.82	1.92	2.743 (2)	179

Experimental details

Crystal data
Chemical formula	[Ni(SO₄)(C₁₂H₈N₂)₂]·C₃H₈O₂
M_r	591.26
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	223
a, b, c (Å)	18.243 (4), 12.440 (3), 13.180 (3)
β (°)	121.58 (3)
V (Å³)	2548.2 (13)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.90
Crystal size (mm)	0.55 × 0.50 × 0.40

Data collection
Diffractometer	Rigaku Mercury CCD diffractometer
Absorption correction	Multi-scan (REQAB: Jacobson, 1998)
T_min, T_max	0.750, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	7078, 2877, 2630
R_int	0.017
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.093, 1.05
No. of reflections	2877
No. of parameters	179
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.79, −0.42

Computer programs: CrystalClear (Rigaku, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP in SHELXTL (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected geometric parameters (Å, º) top

Ni1—N2	2.0775 (16)	S1—O2	1.4559 (14)
Ni1—N1	2.0802 (16)	S1—O1	1.4950 (14)
Ni1—O1	2.1127 (14)

N2—Ni1—N1	80.05 (6)	O1ⁱ—Ni1—O1	67.73 (7)

Symmetry code: (i) −x+1, y, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O2	0.82	1.92	2.743 (2)	178.8

Acknowledgements

This work was supported by the Scientific Research Foundation of Nanjing College of Chemical Technology (grant No. NHKY-2010-17) and Undergraduate Scientific and Technological Innovation Project of Nanjing College of Chemical Technology (2009).

References

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