Bis(1,10-phenanthroline-κ2N,N′)(sulfato-κ2O,O′)nickel(II) butane-2,3-diol monosolvate

Zhong, K.-L.; Ni, C.

doi:10.1107/S1600536812047241

metal-organic compounds

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Volume 68| Part 12| December 2012| Page m1519

doi:10.1107/S1600536812047241

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Bis(1,10-phenanthroline-κ²N,N′)(sulfato-κ²O,O′)nickel(II) butane-2,3-diol monosolvate

Kai-Long Zhong ^a ^* and Chao Ni ^a

^aDepartment of Applied Chemistry, Nanjing College of Chemical Technology, Nanjing, 210048, People's Republic of China
^*Correspondence e-mail: zklong76@163.com

(Received 8 November 2012; accepted 16 November 2012; online 24 November 2012)

In the title compound, [Ni(SO₄)(C₁₂H₈N₂)₂]·C₄H₁₀O₂, the Ni^II ion is six-coordinated by four N atoms from two chelating 1,10-phenanthroline ligands and two O atoms from an O,O′-bidentate sulfate anion, resulting in a distorted octahedral geometry for the metal ion. The dihedral angle between the two chelating N₂C₂ groups is 83.82 (12)°. The Ni^II ion, the S atom and the mid-point of the central C—C bond of the butane-2,3-diol solvent molecule lie on a twofold rotation axis. In the crystal, the complex molecules and solvent molecules are held together by pairs of symmetry-related O_diol—H⋯O_sulfate hydrogen bonds involving the uncoordinating O atoms of the sulfate ions. The solvent molecule is disordered over two sets of sites with site occupancies of 0.450 (9) and 0.550 (9).

Related literature

For the ethane-1,2-diol analog of the title complex, see: Zhong et al. (2009 ). For the propane-1,3-diol analog of the title complex, see: Ni et al. (2010 ). For an isotypic structure, see: Wang & Zhong (2011 ).

Experimental

Crystal data

[Ni(SO₄)(C₁₂H₈N₂)₂]·C₄H₁₀O₂
M_r = 605.29
Monoclinic, C 2/c
a = 18.147 (4) Å
b = 13.051 (3) Å
c = 13.259 (3) Å
β = 122.43 (3)°
V = 2650.5 (14) Å³
Z = 4
Mo Kα radiation
μ = 0.86 mm⁻¹
T = 223 K
0.35 × 0.30 × 0.20 mm

Data collection

Rigaku Mercury CCD diffractometer
Absorption correction: multi-scan (REQAB: Jacobson, 1998 ) T_min = 0.736, T_max = 1.000
6326 measured reflections
2325 independent reflections
1964 reflections with I > 2σ(I)
R_int = 0.035

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.108
S = 1.14
2325 reflections
210 parameters
56 restraints
H-atom parameters constrained
Δρ_max = 0.39 e Å⁻³
Δρ_min = −0.39 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3A⋯O2	0.82	1.97	2.729 (7)	154
O3′—H3′A⋯O2	0.82	2.03	2.769 (8)	150

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/S1600536812047241/mw2096sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812047241/mw2096Isup2.hkl

checkCIF report

Comment top

In the past few years, we have synthesized and reported many Ni-Phen complexes with interesting four-membered chelate rings via a solvothermal reaction. e.g. [NiSO₄(C₁₂H₈N₂)₂].C₂H₆O₂ (Zhong et al., 2009), (II) and [NiSO₄(C₁₂H₈N₂)₂].C₃H₈O₂ (Ni et al., 2010), (III). The title nickel complex, [NiSO₄(C₁₂H₈N₂)₂].C₄H₁₀O₂, (I), is isotypic with the previously reported cobalt(II) structure (Wang & Zhong, 2011).

The Ni²⁺ ion, the S atom and the mid-point of C—C bond of the butane-2,3-diol solvent molecule lie on a crystallographic 2-fold axis. The nickel ion is six-coordinated by four N atoms from two chelating 1,10-phenanthroline ligands and two O atoms from an O,O'-bidentate sulfate ion, in a distorted NiN₄O₂ octahedral environment (Fig. 1). The Ni—N bond distances [2.075 (3) - 2.086 (3) Å], the Ni—O bond distances [2.103 (2) Å], the N—Ni—N bite angle [79.90 (11)°], the O—Ni—O bite angle [68.06 (12)°]m and the dihedral angle between the two chelating NCCN groups [83.82 (12)°] are in good agreement with those observed in (II) and (III).

In the title compound crystal, the neutral monomeric [NiSO₄(C₁₀H₈N₂)₂] complex and the butane-2,3-diol solvent molecule are connected by a pair of symmetry-related intermolecular O—H···O hydrogen bonds with the uncoordinated O atoms of the sulfate ligand (Fig.1 and Table 1).

The solvent molecule is disordered over two positions and was refined with a site occupancy ratio of 0.45:0.55.

Related literature top

For the ethane-1,2-diol analog of the title complex, see: Zhong et al. (2009). For the propane-1,3-diol analog of the title complex, see: Ni et al. (2010). For an isotypic structure, see: Wang & Zhong (2011).

Experimental top

The single crystals of the title compound were obtained by a procedure similar to that described preiously (Wang & Zhong, 2011), but with NiSO₄.7H₂O in place of CoSO₄.7H₂O.

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. Figure 1. The molecular structure of (I) showing the atom-numbering scheme and with displacement ellipsoids drawn at the 35% probability level. The dashed lines depict 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) butane-2,3-diol monosolvate top

Crystal data top

[Ni(SO₄)(C₁₂H₈N₂)₂]·C₄H₁₀O₂	F(000) = 1256
M_r = 605.29	D_x = 1.517 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 5284 reflections
a = 18.147 (4) Å	θ = 3.1–25.0°
b = 13.051 (3) Å	µ = 0.86 mm⁻¹
c = 13.259 (3) Å	T = 223 K
β = 122.43 (3)°	Block, blue
V = 2650.5 (14) Å³	0.35 × 0.30 × 0.20 mm
Z = 4

Data collection top

Rigaku Mercury CCD diffractometer	2325 independent reflections
Radiation source: fine-focus sealed tube	1964 reflections with I > 2σ(I)
Graphite Monochromator monochromator	R_int = 0.035
Detector resolution: 28.5714 pixels mm^-1	θ_max = 25.0°, θ_min = 3.2°
ω scans	h = −21→19
Absorption correction: multi-scan (REQAB: Jacobson, 1998)	k = −15→14
T_min = 0.736, T_max = 1.000	l = −13→15
6326 measured reflections

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.108	H-atom parameters constrained
S = 1.14	w = 1/[σ²(F_o²) + (0.0472P)² + 2.5256P] where P = (F_o² + 2F_c²)/3
2325 reflections	(Δ/σ)_max = 0.006
210 parameters	Δρ_max = 0.39 e Å⁻³
56 restraints	Δρ_min = −0.39 e Å⁻³

Crystal data top

[Ni(SO₄)(C₁₂H₈N₂)₂]·C₄H₁₀O₂	V = 2650.5 (14) Å³
M_r = 605.29	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 18.147 (4) Å	µ = 0.86 mm⁻¹
b = 13.051 (3) Å	T = 223 K
c = 13.259 (3) Å	0.35 × 0.30 × 0.20 mm
β = 122.43 (3)°

Data collection top

Rigaku Mercury CCD diffractometer	2325 independent reflections
Absorption correction: multi-scan (REQAB: Jacobson, 1998)	1964 reflections with I > 2σ(I)
T_min = 0.736, T_max = 1.000	R_int = 0.035
6326 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	56 restraints
wR(F²) = 0.108	H-atom parameters constrained
S = 1.14	Δρ_max = 0.39 e Å⁻³
2325 reflections	Δρ_min = −0.39 e Å⁻³
210 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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Ni1	0.5000	0.32087 (4)	0.2500	0.0327 (2)
S1	0.5000	0.52556 (8)	0.2500	0.0338 (3)
O1	0.56037 (14)	0.45442 (17)	0.3492 (2)	0.0396 (6)
O2	0.45146 (16)	0.58892 (18)	0.2856 (2)	0.0478 (7)
O3	0.4425 (6)	0.7955 (5)	0.3087 (10)	0.108 (3)	0.550 (9)
H3A	0.4578	0.7392	0.2992	0.163*	0.550 (9)
O3'	0.4035 (5)	0.7861 (6)	0.1968 (10)	0.087 (3)	0.450 (9)
H3'A	0.4351	0.7392	0.2388	0.130*	0.450 (9)
N1	0.40659 (17)	0.21783 (19)	0.1282 (2)	0.0340 (7)
N2	0.42127 (17)	0.3083 (2)	0.3190 (2)	0.0349 (6)
C1	0.3964 (2)	0.1793 (3)	0.0285 (3)	0.0434 (9)
H1A	0.4366	0.1969	0.0082	0.052*
C2	0.3278 (3)	0.1135 (3)	−0.0468 (3)	0.0505 (10)
H2A	0.3229	0.0879	−0.1156	0.061*
C3	0.2678 (2)	0.0866 (3)	−0.0195 (3)	0.0459 (9)
H3B	0.2222	0.0426	−0.0691	0.055*
C4	0.2756 (2)	0.1262 (3)	0.0841 (3)	0.0377 (8)
C5	0.2166 (2)	0.1035 (3)	0.1210 (3)	0.0482 (9)
H5A	0.1709	0.0580	0.0761	0.058*
C6	0.2254 (2)	0.1464 (3)	0.2196 (3)	0.0497 (10)
H6A	0.1860	0.1297	0.2416	0.060*
C7	0.2946 (2)	0.2173 (3)	0.2906 (3)	0.0412 (9)
C8	0.3046 (3)	0.2696 (3)	0.3896 (3)	0.0524 (10)
H8A	0.2662	0.2572	0.4144	0.063*
C9	0.3709 (3)	0.3388 (3)	0.4497 (3)	0.0512 (10)
H9A	0.3776	0.3739	0.5152	0.061*
C10	0.4280 (2)	0.3563 (3)	0.4125 (3)	0.0435 (9)
H10A	0.4729	0.4033	0.4545	0.052*
C11	0.3548 (2)	0.2399 (2)	0.2583 (3)	0.0344 (8)
C12	0.3464 (2)	0.1929 (2)	0.1549 (3)	0.0321 (7)
C13	0.4921 (10)	0.8683 (7)	0.3028 (11)	0.093 (4)	0.550 (9)
H13A	0.5499	0.8622	0.3764	0.112*	0.550 (9)
C13'	0.4499 (5)	0.8753 (8)	0.2301 (12)	0.077 (4)	0.450 (9)
H13C	0.4167	0.9346	0.1816	0.092*	0.450 (9)
C14	0.4532 (8)	0.9682 (7)	0.3136 (10)	0.089 (3)	0.550 (9)
H14A	0.4484	0.9651	0.3822	0.134*	0.550 (9)
H14B	0.3963	0.9781	0.2430	0.134*	0.550 (9)
H14C	0.4903	1.0244	0.3222	0.134*	0.550 (9)
C14'	0.5030 (14)	0.8961 (18)	0.3636 (13)	0.142 (7)	0.450 (9)
H14G	0.4644	0.9039	0.3918	0.213*	0.450 (9)
H14H	0.5362	0.9578	0.3791	0.213*	0.450 (9)
H14I	0.5419	0.8398	0.4043	0.213*	0.450 (9)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.0246 (3)	0.0300 (3)	0.0387 (4)	0.000	0.0139 (3)	0.000
S1	0.0230 (6)	0.0294 (6)	0.0429 (7)	0.000	0.0136 (5)	0.000
O1	0.0278 (12)	0.0351 (12)	0.0397 (13)	−0.0009 (10)	0.0073 (10)	−0.0017 (11)
O2	0.0398 (14)	0.0416 (14)	0.0680 (17)	0.0050 (11)	0.0329 (14)	−0.0031 (12)
O3	0.146 (6)	0.052 (4)	0.179 (8)	−0.003 (4)	0.122 (6)	−0.001 (4)
O3'	0.071 (5)	0.068 (5)	0.122 (7)	0.005 (4)	0.052 (5)	0.029 (5)
N1	0.0290 (15)	0.0309 (14)	0.0401 (16)	0.0016 (12)	0.0171 (13)	−0.0019 (13)
N2	0.0288 (14)	0.0331 (14)	0.0382 (15)	−0.0034 (12)	0.0149 (13)	−0.0050 (13)
C1	0.042 (2)	0.044 (2)	0.046 (2)	−0.0014 (17)	0.0244 (18)	−0.0082 (18)
C2	0.046 (2)	0.055 (2)	0.043 (2)	0.0032 (19)	0.0181 (18)	−0.0138 (19)
C3	0.0336 (19)	0.042 (2)	0.047 (2)	−0.0028 (16)	0.0113 (17)	−0.0106 (18)
C4	0.0285 (17)	0.0323 (18)	0.0418 (19)	−0.0010 (14)	0.0119 (15)	−0.0012 (16)
C5	0.0339 (19)	0.047 (2)	0.050 (2)	−0.0108 (17)	0.0139 (17)	−0.0034 (19)
C6	0.0329 (19)	0.060 (2)	0.055 (2)	−0.0110 (18)	0.0234 (18)	0.004 (2)
C7	0.0314 (19)	0.050 (2)	0.041 (2)	−0.0002 (16)	0.0182 (16)	0.0049 (17)
C8	0.046 (2)	0.074 (3)	0.046 (2)	−0.004 (2)	0.031 (2)	−0.001 (2)
C9	0.053 (2)	0.061 (2)	0.042 (2)	−0.001 (2)	0.0276 (19)	−0.0101 (19)
C10	0.040 (2)	0.043 (2)	0.042 (2)	−0.0033 (17)	0.0192 (17)	−0.0079 (17)
C11	0.0274 (17)	0.0331 (17)	0.0362 (18)	0.0022 (14)	0.0127 (15)	0.0017 (15)
C12	0.0252 (16)	0.0294 (16)	0.0351 (18)	0.0039 (13)	0.0117 (14)	0.0041 (14)
C13	0.118 (8)	0.075 (6)	0.114 (8)	−0.004 (6)	0.080 (7)	0.011 (6)
C13'	0.067 (7)	0.069 (7)	0.102 (8)	0.000 (5)	0.051 (6)	0.016 (6)
C14	0.107 (7)	0.090 (6)	0.110 (7)	0.020 (5)	0.084 (6)	0.018 (5)
C14'	0.153 (10)	0.180 (11)	0.130 (9)	−0.013 (8)	0.100 (8)	0.017 (8)

Geometric parameters (Å, º) top

Ni1—N2ⁱ	2.075 (3)	C4—C5	1.427 (5)
Ni1—N2	2.075 (3)	C5—C6	1.350 (5)
Ni1—N1	2.086 (3)	C5—H5A	0.9300
Ni1—N1ⁱ	2.086 (3)	C6—C7	1.433 (5)
Ni1—O1	2.103 (2)	C6—H6A	0.9300
Ni1—O1ⁱ	2.103 (2)	C7—C11	1.402 (5)
Ni1—S1	2.6714 (14)	C7—C8	1.402 (5)
S1—O2ⁱ	1.459 (2)	C8—C9	1.368 (5)
S1—O2	1.459 (2)	C8—H8A	0.9300
S1—O1ⁱ	1.499 (2)	C9—C10	1.384 (5)
S1—O1	1.499 (2)	C9—H9A	0.9300
O3—C13	1.340 (9)	C10—H10A	0.9300
O3—H3A	0.8200	C11—C12	1.435 (5)
O3'—C13'	1.362 (9)	C13—C14	1.526 (10)
O3'—H3'A	0.8200	C13—C13ⁱ	1.572 (14)
N1—C1	1.332 (4)	C13—H13A	0.9800
N1—C12	1.355 (4)	C13'—C14'	1.519 (11)
N2—C10	1.335 (4)	C13'—C13'ⁱ	1.600 (14)
N2—C11	1.363 (4)	C13'—H13C	0.9800
C1—C2	1.398 (5)	C14—H14A	0.9600
C1—H1A	0.9300	C14—H14B	0.9600
C2—C3	1.365 (5)	C14—H14C	0.9600
C2—H2A	0.9300	C14'—H14G	0.9600
C3—C4	1.401 (5)	C14'—H14H	0.9600
C3—H3B	0.9300	C14'—H14I	0.9600
C4—C12	1.412 (5)

N2ⁱ—Ni1—N2	170.97 (15)	C3—C4—C5	124.0 (3)
N2ⁱ—Ni1—N1	94.23 (11)	C12—C4—C5	118.8 (3)
N2—Ni1—N1	79.90 (11)	C6—C5—C4	121.7 (3)
N2ⁱ—Ni1—N1ⁱ	79.90 (11)	C6—C5—H5A	119.1
N2—Ni1—N1ⁱ	94.23 (11)	C4—C5—H5A	119.1
N1—Ni1—N1ⁱ	99.75 (15)	C5—C6—C7	120.7 (3)
N2ⁱ—Ni1—O1	95.18 (10)	C5—C6—H6A	119.7
N2—Ni1—O1	92.30 (10)	C7—C6—H6A	119.7
N1—Ni1—O1	162.31 (9)	C11—C7—C8	116.9 (3)
N1ⁱ—Ni1—O1	96.63 (10)	C11—C7—C6	119.2 (3)
N2ⁱ—Ni1—O1ⁱ	92.30 (10)	C8—C7—C6	123.9 (3)
N2—Ni1—O1ⁱ	95.18 (10)	C9—C8—C7	119.9 (4)
N1—Ni1—O1ⁱ	96.63 (10)	C9—C8—H8A	120.1
N1ⁱ—Ni1—O1ⁱ	162.31 (9)	C7—C8—H8A	120.1
O1—Ni1—O1ⁱ	68.06 (12)	C8—C9—C10	119.6 (4)
N2ⁱ—Ni1—S1	94.52 (7)	C8—C9—H9A	120.2
N2—Ni1—S1	94.52 (7)	C10—C9—H9A	120.2
N1—Ni1—S1	130.13 (7)	N2—C10—C9	122.7 (3)
N1ⁱ—Ni1—S1	130.13 (7)	N2—C10—H10A	118.6
O1—Ni1—S1	34.03 (6)	C9—C10—H10A	118.6
O1ⁱ—Ni1—S1	34.03 (6)	N2—C11—C7	123.1 (3)
O2ⁱ—S1—O2	110.9 (2)	N2—C11—C12	116.8 (3)
O2ⁱ—S1—O1ⁱ	110.55 (14)	C7—C11—C12	120.1 (3)
O2—S1—O1ⁱ	110.56 (14)	N1—C12—C4	123.2 (3)
O2ⁱ—S1—O1	110.56 (14)	N1—C12—C11	117.3 (3)
O2—S1—O1	110.55 (14)	C4—C12—C11	119.4 (3)
O1ⁱ—S1—O1	103.47 (18)	O3—C13—C14	103.9 (8)
O2ⁱ—S1—Ni1	124.53 (11)	O3—C13—C13ⁱ	120.1 (10)
O2—S1—Ni1	124.53 (11)	C14—C13—C13ⁱ	113.5 (7)
O1ⁱ—S1—Ni1	51.74 (9)	O3—C13—H13A	106.1
O1—S1—Ni1	51.74 (9)	C14—C13—H13A	106.1
S1—O1—Ni1	94.23 (11)	C13ⁱ—C13—H13A	106.1
C13—O3—H3A	109.5	O3'—C13'—C14'	115.2 (14)
C13'—O3'—H3'A	109.5	O3'—C13'—C13'ⁱ	120.1 (5)
C1—N1—C12	117.8 (3)	C14'—C13'—C13'ⁱ	73.6 (11)
C1—N1—Ni1	129.3 (2)	O3'—C13'—H13C	114.0
C12—N1—Ni1	112.8 (2)	C14'—C13'—H13C	114.0
C10—N2—C11	117.8 (3)	C13'ⁱ—C13'—H13C	114.0
C10—N2—Ni1	129.1 (2)	C13—C14—H14A	109.5
C11—N2—Ni1	113.1 (2)	C13—C14—H14B	109.5
N1—C1—C2	122.4 (4)	H14A—C14—H14B	109.5
N1—C1—H1A	118.8	C13—C14—H14C	109.5
C2—C1—H1A	118.8	H14A—C14—H14C	109.5
C3—C2—C1	120.1 (4)	H14B—C14—H14C	109.5
C3—C2—H2A	120.0	C13'—C14'—H14G	109.5
C1—C2—H2A	120.0	C13'—C14'—H14H	109.5
C2—C3—C4	119.3 (3)	H14G—C14'—H14H	109.5
C2—C3—H3B	120.3	C13'—C14'—H14I	109.5
C4—C3—H3B	120.3	H14G—C14'—H14I	109.5
C3—C4—C12	117.2 (3)	H14H—C14'—H14I	109.5

N2ⁱ—Ni1—S1—O2ⁱ	−2.57 (14)	O1ⁱ—Ni1—N2—C10	−82.1 (3)
N2—Ni1—S1—O2ⁱ	177.43 (14)	S1—Ni1—N2—C10	−47.9 (3)
N1—Ni1—S1—O2ⁱ	−101.97 (16)	N1—Ni1—N2—C11	2.9 (2)
N1ⁱ—Ni1—S1—O2ⁱ	78.03 (16)	N1ⁱ—Ni1—N2—C11	−96.3 (2)
O1—Ni1—S1—O2ⁱ	90.01 (17)	O1—Ni1—N2—C11	166.9 (2)
O1ⁱ—Ni1—S1—O2ⁱ	−89.99 (17)	O1ⁱ—Ni1—N2—C11	98.7 (2)
N2ⁱ—Ni1—S1—O2	177.43 (14)	S1—Ni1—N2—C11	132.9 (2)
N2—Ni1—S1—O2	−2.57 (14)	C12—N1—C1—C2	−1.3 (5)
N1—Ni1—S1—O2	78.03 (16)	Ni1—N1—C1—C2	−177.4 (3)
N1ⁱ—Ni1—S1—O2	−101.97 (16)	N1—C1—C2—C3	0.2 (6)
O1—Ni1—S1—O2	−89.99 (17)	C1—C2—C3—C4	0.4 (5)
O1ⁱ—Ni1—S1—O2	90.01 (17)	C2—C3—C4—C12	0.2 (5)
N2ⁱ—Ni1—S1—O1ⁱ	87.43 (14)	C2—C3—C4—C5	179.8 (3)
N2—Ni1—S1—O1ⁱ	−92.57 (14)	C3—C4—C5—C6	−177.7 (4)
N1—Ni1—S1—O1ⁱ	−11.98 (16)	C12—C4—C5—C6	1.9 (5)
N1ⁱ—Ni1—S1—O1ⁱ	168.02 (16)	C4—C5—C6—C7	0.4 (6)
O1—Ni1—S1—O1ⁱ	180.0	C5—C6—C7—C11	−1.6 (6)
N2ⁱ—Ni1—S1—O1	−92.57 (14)	C5—C6—C7—C8	175.9 (4)
N2—Ni1—S1—O1	87.43 (14)	C11—C7—C8—C9	−0.1 (5)
N1—Ni1—S1—O1	168.02 (16)	C6—C7—C8—C9	−177.6 (4)
N1ⁱ—Ni1—S1—O1	−11.98 (16)	C7—C8—C9—C10	−0.3 (6)
O1ⁱ—Ni1—S1—O1	180.0	C11—N2—C10—C9	0.3 (5)
O2ⁱ—S1—O1—Ni1	−118.38 (13)	Ni1—N2—C10—C9	−178.9 (3)
O2—S1—O1—Ni1	118.39 (13)	C8—C9—C10—N2	0.2 (6)
O1ⁱ—S1—O1—Ni1	0.0	C10—N2—C11—C7	−0.8 (5)
N2ⁱ—Ni1—O1—S1	90.40 (12)	Ni1—N2—C11—C7	178.5 (3)
N2—Ni1—O1—S1	−94.66 (12)	C10—N2—C11—C12	177.2 (3)
N1—Ni1—O1—S1	−31.5 (4)	Ni1—N2—C11—C12	−3.5 (3)
N1ⁱ—Ni1—O1—S1	170.81 (12)	C8—C7—C11—N2	0.7 (5)
O1ⁱ—Ni1—O1—S1	0.0	C6—C7—C11—N2	178.3 (3)
N2ⁱ—Ni1—N1—C1	−12.5 (3)	C8—C7—C11—C12	−177.3 (3)
N2—Ni1—N1—C1	174.4 (3)	C6—C7—C11—C12	0.4 (5)
N1ⁱ—Ni1—N1—C1	−93.0 (3)	C1—N1—C12—C4	1.9 (4)
O1—Ni1—N1—C1	109.5 (4)	Ni1—N1—C12—C4	178.6 (2)
O1ⁱ—Ni1—N1—C1	80.3 (3)	C1—N1—C12—C11	−176.1 (3)
S1—Ni1—N1—C1	87.0 (3)	Ni1—N1—C12—C11	0.6 (3)
N2ⁱ—Ni1—N1—C12	171.2 (2)	C3—C4—C12—N1	−1.3 (5)
N2—Ni1—N1—C12	−1.9 (2)	C5—C4—C12—N1	179.0 (3)
N1ⁱ—Ni1—N1—C12	90.7 (2)	C3—C4—C12—C11	176.6 (3)
O1—Ni1—N1—C12	−66.8 (4)	C5—C4—C12—C11	−3.1 (5)
O1ⁱ—Ni1—N1—C12	−96.0 (2)	N2—C11—C12—N1	1.9 (4)
S1—Ni1—N1—C12	−89.3 (2)	C7—C11—C12—N1	180.0 (3)
N1—Ni1—N2—C10	−177.9 (3)	N2—C11—C12—C4	−176.1 (3)
N1ⁱ—Ni1—N2—C10	82.9 (3)	C7—C11—C12—C4	1.9 (5)
O1—Ni1—N2—C10	−13.9 (3)

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—H3A···O2	0.82	1.97	2.729 (7)	154
O3′—H3′A···O2	0.82	2.03	2.769 (8)	150

Experimental details

Crystal data
Chemical formula	[Ni(SO₄)(C₁₂H₈N₂)₂]·C₄H₁₀O₂
M_r	605.29
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	223
a, b, c (Å)	18.147 (4), 13.051 (3), 13.259 (3)
β (°)	122.43 (3)
V (Å³)	2650.5 (14)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.86
Crystal size (mm)	0.35 × 0.30 × 0.20

Data collection
Diffractometer	Rigaku Mercury CCD diffractometer
Absorption correction	Multi-scan (REQAB: Jacobson, 1998)
T_min, T_max	0.736, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	6326, 2325, 1964
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.594

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.108, 1.14
No. of reflections	2325
No. of parameters	210
No. of restraints	56
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.39, −0.39

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···O2	0.82	1.97	2.729 (7)	154
O3'—H3'A···O2	0.82	2.03	2.769 (8)	150

Acknowledgements

This work was supported by the Scientific Research Foundation of Nanjing College of Chemical Technology (grant No. NHKY-2010-17).

References

Jacobson, R. (1998). REQAB. Molecular Structure Corporation, The Woodlands, Texas, USA. Google Scholar
Ni, C., Zhong, K.-L. & Cui, J.-D. (2010). Acta Cryst. E66, m746–m747. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Rigaku (2007). CrystalClear. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wang, S.-J. & Zhong, K.-L. (2011). Acta Cryst. E67, m446. Web of Science CSD CrossRef IUCr Journals Google Scholar
Zhong, K.-L., Ni, C. & Wang, J.-M. (2009). Acta Cryst. E65, m911. Web of Science CSD CrossRef IUCr Journals Google Scholar

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