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

Zhong, K.-L.; Duan, C.-X.

doi:10.1107/S1600536813023027

metal-organic compounds

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ISSN: 2056-9890

Volume 69| Part 9| September 2013| Pages m506-m507

doi:10.1107/S1600536813023027

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

Kai-Long Zhong ^a ^* and Cheng-Xian Duan ^b

^aDepartment of Applied Chemistry, Nanjing College of Chemical Technology, Nanjing, 210048, People's Republic of China, and ^bAVIC Hefei Jianghang Aircraft Equipment Corporation Ltd, Hefei, 230051, People's Republic of China
^*Correspondence e-mail: zklong76@163.com

(Received 14 August 2013; accepted 15 August 2013; online 21 August 2013)

In the title compound, [Ni(SO₄)(C₁₂H₈N₂)₂]·C₃H₈O₂, the Ni^II atom exhibits a distorted octahedral coordination by four N atoms from two chelating 1,10-phenanthroline ligands and two O atoms from an O,O′-bidentate sulfate group. A twofold rotation axis passes through the Ni and S atoms and the mid-point of the hydroxyl C—C bond of the propane-1,2-diol solvent molecule. The dihedral angle between the two chelating N₂C₂ groups is 85.61 (8)°. The [NiSO₄(C₁₀H₈N₂)₂] and propane-1,2-diol units are held together by a pair of symmetry-related intermolecular O—H⋯O hydrogen bonds involving the uncoordinating O atoms of the sulfate ion. Due to symmetry, the solvent molecule is equally disordered over two positions.

Related literature

For the ethane-1,2-diol solvate of the title complex, see: Zhong et al. (2009 ). For the propane-1,3-diol solvate of the title complex, see: Ni et al. (2010 ). For the butane-2,3-diol solvate of the title complex, see: Zhong & Ni (2012 ). For an isotypic compound, see: Zhong (2013 ). For background to coordination polymers, see: Batten & Robson (1998 ); Zhang et al. (2010 ); Zhong et al. (2011 ).

Experimental

Crystal data

[Ni(SO₄)(C₁₂H₈N₂)₂]·C₃H₈O₂
M_r = 591.27
Monoclinic, C 2/c
a = 18.0277 (10) Å
b = 13.0448 (5) Å
c = 12.8070 (5) Å
β = 121.738 (5)°
V = 2561.4 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.89 mm⁻¹
T = 223 K
0.30 × 0.25 × 0.15 mm

Data collection

Rigaku Mercury CCD diffractometer
Absorption correction: multi-scan (REQAB; Jacobson, 1998 ) T_min = 0.876, T_max = 1.000
7993 measured reflections
2602 independent reflections
2311 reflections with I > 2σ(I)
R_int = 0.031

Refinement

R[F² > 2σ(F²)] = 0.034
wR(F²) = 0.084
S = 1.01
2602 reflections
191 parameters
26 restraints
H-atom parameters constrained
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.42 e Å⁻³

Table 1
Selected bond lengths (Å)

Ni1—N1	2.0762 (19)
Ni1—N2	2.082 (2)
Ni1—O1	2.1074 (16)
S1—O2	1.4587 (17)
S1—O1	1.4942 (16)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3B⋯O2	0.82	1.97	2.705 (6)	148
O3′—H3′A⋯O2	0.82	2.00	2.767 (8)	155

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/S1600536813023027/zq2207sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813023027/zq2207Isup2.hkl

checkCIF report

Comment top

The self-assembly of coordination polymers and the crystal engineering of metal-organic coordination frameworks have recently attracted great interest, owing to their interesting structural topologies and potential application as functional materials (Batten & Robson, 1998; Zhang et al., 2010; Zhong et al., 2011). The neutral bidentate ligand 1,10-phenanthroline (phen) as an auxiliary ligand has been widely applied in constructing interesting coordination polymers. Recently, we have obtained unexpectedly some nickel-phen complexes (Zhong et al., 2009; Ni et al., 2010; Zhong & Ni, 2012) with interesting four-membered chelating rings during attempts to synthesize mixed-ligand coordination polymers with phen as auxiliary ligand via an alcohol-solvothermal reaction. We here report the title compound, [NiSO₄(C₁₂H₈N₂)₂]. C₃H₈O₂, which is the part of our systematic investigation of transition metal nickel complexes with bidentate bridging sulfate ligands. It is isostructural to the previously reported cobalt(II) analog (Zhong, 2013).

The single-crystal X-ray diffraction experiment revealed that the crystal structure of the the title compound consists of a neutral monomeric [NiSO₄(C₁₀H₈N₂)₂] complex and a solvent propane-1,2-diol molecule. A two-fold rotation axis (symmetry code: -x + 1, y, -z + 1/2) passes through the Ni and S atoms, and the mid-point of the hydroxyl C—C bond of the propane-1,2-diol solvent molecule is likewise located on a the same crystallographic axis. The Ni^II metal ion has a distorted NiN₄O₂ octahedral geometry, with four N atoms from two chelating phenanthroline ligands and two O atoms from an O,O'-bidentate sulfate anion (Fig. 1). The Ni—O bond distance of 2.107 (2) Å, the O—Ni—O bite angle of 67.95 (9)°, the Ni—N bond distances in the range of 2.076 (2)–2.082 (2) Å, the N—Ni—N bite angle of 80.09 (7)° and the dihedral angle of 85.61 (8)° between the two chelating NCCN groups are in good agreement with those observed in the previously reported nickel complexes (Zhong et al., 2009; Ni et al., 2010; Zhong & Ni, 2012) (Table 1).

The solvent molecule is disordered over two positions and was refined with a site-occupancy ratio of 0.50:0.50. The metal complex and the solvent molecules are held together by a pair of intermolecular O—H···O hydrogen bonds, which help to further stabilize the crystal structure (Fig.1 and Table 2).

Related literature top

For the ethane-1,2-diol solvate of the title complex, see: Zhong et al. (2009). For the propane-1,3-diol solvate of the title complex, see: Ni et al. (2010). For the butane-2,3-diol solvate of the title complex, see: Zhong & Ni (2012). For an isotypic compound, see: Zhong (2013). For background to coordination polymers, see: Batten & Robson (1998); Zhang et al. (2010); Zhong et al. (2011).

Experimental top

Green block-shaped crystals of the title compound were obtained by a procedure similar to that described previously (Zhong, 2013), 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. The molecular structure showing the atom-numbering scheme and with displacement ellipsoids drawn at the 30% probability level. The light broken lines depict O—H···O interactions. Unlabeled atoms are related to the labelled atoms by the symmetry operator (-x, y, -z + 1/2).

Bis(1,10-phenanthroline-κ²N,N')(sulfato-κ²O,O')nickel(II) propane-1,2-diol monosolvate top

Crystal data top

[Ni(SO₄)(C₁₂H₈N₂)₂]·C₃H₈O₂	F(000) = 1224
M_r = 591.27	D_x = 1.533 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 3439 reflections
a = 18.0277 (10) Å	θ = 3.6–28.8°
b = 13.0448 (5) Å	µ = 0.89 mm⁻¹
c = 12.8070 (5) Å	T = 223 K
β = 121.738 (5)°	Block, green
V = 2561.4 (2) Å³	0.30 × 0.25 × 0.15 mm
Z = 4

Data collection top

Rigaku Mercury CCD diffractometer	2602 independent reflections
Radiation source: fine-focus sealed tube	2311 reflections with I > 2σ(I)
Graphite Monochromator monochromator	R_int = 0.031
Detector resolution: 28.5714 pixels mm^-1	θ_max = 26.4°, θ_min = 3.1°
ω scans	h = −21→22
Absorption correction: multi-scan (REQAB; Jacobson, 1998)	k = −16→16
T_min = 0.876, T_max = 1.000	l = −16→14
7993 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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.084	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0343P)² + 4.7899P] where P = (F_o² + 2F_c²)/3
2602 reflections	(Δ/σ)_max < 0.001
191 parameters	Δρ_max = 0.32 e Å⁻³
26 restraints	Δρ_min = −0.42 e Å⁻³

Crystal data top

[Ni(SO₄)(C₁₂H₈N₂)₂]·C₃H₈O₂	V = 2561.4 (2) Å³
M_r = 591.27	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 18.0277 (10) Å	µ = 0.89 mm⁻¹
b = 13.0448 (5) Å	T = 223 K
c = 12.8070 (5) Å	0.30 × 0.25 × 0.15 mm
β = 121.738 (5)°

Data collection top

Rigaku Mercury CCD diffractometer	2602 independent reflections
Absorption correction: multi-scan (REQAB; Jacobson, 1998)	2311 reflections with I > 2σ(I)
T_min = 0.876, T_max = 1.000	R_int = 0.031
7993 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	26 restraints
wR(F²) = 0.084	H-atom parameters constrained
S = 1.01	Δρ_max = 0.32 e Å⁻³
2602 reflections	Δρ_min = −0.42 e Å⁻³
191 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	0.0000	0.18120 (3)	0.2500	0.02136 (14)
S1	0.0000	−0.02326 (6)	0.2500	0.02110 (19)
O1	0.05906 (10)	0.04723 (12)	0.35253 (14)	0.0273 (4)
O2	−0.05048 (12)	−0.08688 (14)	0.28419 (17)	0.0364 (4)
O3	−0.0543 (5)	−0.2918 (4)	0.3137 (6)	0.0602 (19)	0.50
H3B	−0.0440	−0.2379	0.2907	0.090*	0.50
O3'	−0.0830 (5)	−0.2955 (5)	0.2536 (7)	0.083 (3)	0.50
H3'A	−0.0580	−0.2399	0.2694	0.124*	0.50
N1	0.08057 (13)	0.19506 (14)	0.18013 (17)	0.0236 (4)
N2	0.09201 (13)	0.28362 (15)	0.37649 (18)	0.0245 (4)
C1	0.07474 (16)	0.14850 (19)	0.0836 (2)	0.0288 (5)
H1A	0.0310	0.1001	0.0411	0.035*
C2	0.13188 (18)	0.1696 (2)	0.0438 (2)	0.0358 (6)
H2A	0.1258	0.1360	−0.0244	0.043*
C3	0.19674 (17)	0.2399 (2)	0.1056 (2)	0.0373 (6)
H3A	0.2352	0.2542	0.0799	0.045*
C4	0.20528 (16)	0.2908 (2)	0.2082 (2)	0.0285 (5)
C5	0.27283 (17)	0.3631 (2)	0.2805 (2)	0.0361 (6)
H5A	0.3117	0.3819	0.2569	0.043*
C6	0.28081 (17)	0.4044 (2)	0.3826 (2)	0.0340 (6)
H6A	0.3259	0.4503	0.4291	0.041*
C7	0.22142 (16)	0.37889 (19)	0.4206 (2)	0.0277 (5)
C8	0.22877 (17)	0.41661 (19)	0.5286 (2)	0.0331 (6)
H8A	0.2738	0.4612	0.5796	0.040*
C9	0.16923 (19)	0.3871 (2)	0.5578 (2)	0.0363 (6)
H9A	0.1736	0.4110	0.6293	0.044*
C10	0.10143 (18)	0.32078 (19)	0.4793 (2)	0.0318 (6)
H10A	0.0611	0.3019	0.5003	0.038*
C11	0.15246 (15)	0.31125 (16)	0.3486 (2)	0.0218 (5)
C12	0.14502 (14)	0.26499 (17)	0.2415 (2)	0.0223 (5)
C13	−0.0251 (5)	−0.3713 (3)	0.2775 (7)	0.133 (3)	0.50
H13	−0.0796	−0.3735	0.1972	0.160*	0.50
C13'	−0.0251 (5)	−0.3713 (3)	0.2775 (7)	0.133 (3)	0.50
H13A	−0.0571	−0.4354	0.2556	0.160*	0.50
H13B	0.0153	−0.3727	0.3657	0.160*	0.50
C14	−0.0365 (6)	−0.4760 (5)	0.3032 (10)	0.088 (3)	0.50
H14A	−0.0732	−0.4774	0.3366	0.133*	0.50
H14B	0.0193	−0.5050	0.3613	0.133*	0.50
H14C	−0.0631	−0.5151	0.2286	0.133*	0.50

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.0205 (2)	0.0205 (2)	0.0254 (2)	0.000	0.01365 (18)	0.000
S1	0.0167 (4)	0.0205 (4)	0.0254 (4)	0.000	0.0106 (3)	0.000
O1	0.0222 (8)	0.0259 (9)	0.0246 (8)	0.0005 (7)	0.0059 (7)	−0.0006 (7)
O2	0.0335 (10)	0.0345 (10)	0.0475 (11)	−0.0061 (8)	0.0258 (9)	0.0048 (8)
O3	0.107 (5)	0.034 (3)	0.082 (4)	−0.010 (3)	0.079 (4)	−0.009 (3)
O3'	0.106 (5)	0.054 (4)	0.120 (6)	−0.040 (4)	0.082 (5)	−0.040 (4)
N1	0.0234 (10)	0.0231 (10)	0.0254 (10)	−0.0011 (8)	0.0137 (9)	−0.0028 (8)
N2	0.0265 (10)	0.0228 (10)	0.0283 (10)	0.0005 (8)	0.0172 (9)	−0.0009 (8)
C1	0.0290 (13)	0.0301 (13)	0.0267 (12)	−0.0032 (11)	0.0143 (11)	−0.0062 (10)
C2	0.0384 (15)	0.0460 (16)	0.0288 (13)	−0.0028 (13)	0.0216 (12)	−0.0084 (12)
C3	0.0333 (14)	0.0554 (18)	0.0323 (13)	−0.0071 (13)	0.0235 (12)	−0.0029 (13)
C4	0.0251 (12)	0.0357 (13)	0.0259 (12)	−0.0036 (11)	0.0142 (10)	0.0011 (10)
C5	0.0275 (13)	0.0482 (16)	0.0349 (14)	−0.0115 (12)	0.0182 (12)	0.0007 (12)
C6	0.0260 (13)	0.0388 (15)	0.0318 (13)	−0.0122 (11)	0.0114 (11)	−0.0031 (11)
C7	0.0260 (12)	0.0265 (12)	0.0265 (11)	−0.0014 (10)	0.0109 (10)	0.0010 (10)
C8	0.0334 (14)	0.0293 (13)	0.0295 (13)	−0.0051 (11)	0.0117 (11)	−0.0068 (11)
C9	0.0463 (16)	0.0357 (14)	0.0310 (13)	−0.0027 (13)	0.0230 (13)	−0.0101 (11)
C10	0.0374 (14)	0.0315 (13)	0.0338 (13)	−0.0017 (11)	0.0239 (12)	−0.0050 (11)
C11	0.0218 (11)	0.0196 (11)	0.0236 (11)	0.0008 (9)	0.0116 (10)	0.0017 (9)
C12	0.0197 (11)	0.0228 (11)	0.0240 (11)	0.0011 (9)	0.0112 (9)	0.0020 (9)
C13	0.227 (7)	0.043 (2)	0.242 (7)	−0.020 (4)	0.201 (7)	−0.011 (4)
C13'	0.227 (7)	0.043 (2)	0.242 (7)	−0.020 (4)	0.201 (7)	−0.011 (4)
C14	0.107 (7)	0.040 (4)	0.155 (9)	0.000 (4)	0.093 (7)	0.001 (5)

Geometric parameters (Å, º) top

Ni1—N1	2.0762 (19)	C3—H3A	0.9300
Ni1—N1ⁱ	2.0762 (19)	C4—C12	1.401 (3)
Ni1—N2	2.082 (2)	C4—C5	1.430 (4)
Ni1—N2ⁱ	2.082 (2)	C5—C6	1.350 (4)
Ni1—O1ⁱ	2.1074 (16)	C5—H5A	0.9300
Ni1—O1	2.1074 (16)	C6—C7	1.429 (3)
S1—O2ⁱ	1.4587 (17)	C6—H6A	0.9300
S1—O2	1.4587 (17)	C7—C11	1.403 (3)
S1—O1	1.4942 (16)	C7—C8	1.408 (3)
S1—O1ⁱ	1.4942 (16)	C8—C9	1.364 (4)
O3—C13	1.350 (4)	C8—H8A	0.9300
O3—H3B	0.8200	C9—C10	1.400 (4)
O3'—H3'A	0.8200	C9—H9A	0.9300
N1—C1	1.331 (3)	C10—H10A	0.9300
N1—C12	1.356 (3)	C11—C12	1.439 (3)
N2—C10	1.328 (3)	C13—C13ⁱ	1.411 (6)
N2—C11	1.362 (3)	C13—C14	1.444 (7)
C1—C2	1.397 (4)	C13—H13	0.9800
C1—H1A	0.9300	C14—H14A	0.9600
C2—C3	1.365 (4)	C14—H14B	0.9600
C2—H2A	0.9300	C14—H14C	0.9600
C3—C4	1.406 (3)

N1—Ni1—N1ⁱ	170.01 (11)	C12—C4—C5	119.6 (2)
N1—Ni1—N2	80.09 (7)	C3—C4—C5	123.6 (2)
N1ⁱ—Ni1—N2	93.46 (7)	C6—C5—C4	120.7 (2)
N1—Ni1—N2ⁱ	93.46 (7)	C6—C5—H5A	119.6
N1ⁱ—Ni1—N2ⁱ	80.09 (7)	C4—C5—H5A	119.6
N2—Ni1—N2ⁱ	100.15 (11)	C5—C6—C7	121.3 (2)
N1—Ni1—O1ⁱ	92.43 (7)	C5—C6—H6A	119.3
N1ⁱ—Ni1—O1ⁱ	95.86 (7)	C7—C6—H6A	119.3
N2—Ni1—O1ⁱ	162.12 (7)	C11—C7—C8	117.3 (2)
N2ⁱ—Ni1—O1ⁱ	96.48 (7)	C11—C7—C6	119.1 (2)
N1—Ni1—O1	95.86 (7)	C8—C7—C6	123.6 (2)
N1ⁱ—Ni1—O1	92.43 (7)	C9—C8—C7	119.3 (2)
N2—Ni1—O1	96.48 (7)	C9—C8—H8A	120.3
N2ⁱ—Ni1—O1	162.12 (7)	C7—C8—H8A	120.3
O1ⁱ—Ni1—O1	67.95 (9)	C8—C9—C10	119.6 (2)
O2ⁱ—S1—O2	110.65 (16)	C8—C9—H9A	120.2
O2ⁱ—S1—O1	110.20 (10)	C10—C9—H9A	120.2
O2—S1—O1	110.79 (10)	N2—C10—C9	123.0 (2)
O2ⁱ—S1—O1ⁱ	110.79 (10)	N2—C10—H10A	118.5
O2—S1—O1ⁱ	110.20 (10)	C9—C10—H10A	118.5
O1—S1—O1ⁱ	104.03 (13)	N2—C11—C7	123.3 (2)
S1—O1—Ni1	94.01 (8)	N2—C11—C12	116.9 (2)
C13—O3—H3B	109.5	C7—C11—C12	119.7 (2)
C1—N1—C12	118.1 (2)	N1—C12—C4	123.4 (2)
C1—N1—Ni1	128.99 (17)	N1—C12—C11	117.2 (2)
C12—N1—Ni1	112.89 (14)	C4—C12—C11	119.4 (2)
C10—N2—C11	117.4 (2)	O3—C13—C13ⁱ	129.8 (4)
C10—N2—Ni1	129.79 (17)	O3—C13—C14	121.4 (5)
C11—N2—Ni1	112.70 (14)	C13ⁱ—C13—C14	108.6 (4)
N1—C1—C2	122.5 (2)	O3—C13—H13	91.5
N1—C1—H1A	118.8	C13ⁱ—C13—H13	91.5
C2—C1—H1A	118.8	C14—C13—H13	91.5
C3—C2—C1	119.5 (2)	C13—C14—H14A	109.5
C3—C2—H2A	120.3	C13—C14—H14B	109.5
C1—C2—H2A	120.3	H14A—C14—H14B	109.5
C2—C3—C4	119.9 (2)	C13—C14—H14C	109.5
C2—C3—H3A	120.0	H14A—C14—H14C	109.5
C4—C3—H3A	120.0	H14B—C14—H14C	109.5
C12—C4—C3	116.7 (2)

O2ⁱ—S1—O1—Ni1	118.81 (10)	C12—C4—C5—C6	2.1 (4)
O2—S1—O1—Ni1	−118.40 (9)	C3—C4—C5—C6	−175.7 (3)
O1ⁱ—S1—O1—Ni1	0.0	C4—C5—C6—C7	−1.2 (4)
N1—Ni1—O1—S1	−90.25 (8)	C5—C6—C7—C11	−1.4 (4)
N1ⁱ—Ni1—O1—S1	95.34 (8)	C5—C6—C7—C8	177.5 (3)
N2—Ni1—O1—S1	−170.90 (8)	C11—C7—C8—C9	−0.6 (4)
N2ⁱ—Ni1—O1—S1	30.8 (3)	C6—C7—C8—C9	−179.4 (2)
O1ⁱ—Ni1—O1—S1	0.0	C7—C8—C9—C10	−0.6 (4)
N2—Ni1—N1—C1	178.4 (2)	C11—N2—C10—C9	0.9 (4)
N2ⁱ—Ni1—N1—C1	−81.9 (2)	Ni1—N2—C10—C9	177.70 (19)
O1ⁱ—Ni1—N1—C1	14.7 (2)	C8—C9—C10—N2	0.5 (4)
O1—Ni1—N1—C1	82.8 (2)	C10—N2—C11—C7	−2.2 (3)
N2—Ni1—N1—C12	−4.41 (15)	Ni1—N2—C11—C7	−179.53 (18)
N2ⁱ—Ni1—N1—C12	95.30 (16)	C10—N2—C11—C12	175.8 (2)
O1ⁱ—Ni1—N1—C12	−168.06 (15)	Ni1—N2—C11—C12	−1.5 (2)
O1—Ni1—N1—C12	−99.98 (15)	C8—C7—C11—N2	2.1 (3)
N1—Ni1—N2—C10	−173.8 (2)	C6—C7—C11—N2	−179.0 (2)
N1ⁱ—Ni1—N2—C10	13.9 (2)	C8—C7—C11—C12	−175.9 (2)
N2ⁱ—Ni1—N2—C10	94.4 (2)	C6—C7—C11—C12	3.0 (3)
O1ⁱ—Ni1—N2—C10	−107.5 (3)	C1—N1—C12—C4	0.3 (3)
O1—Ni1—N2—C10	−78.9 (2)	Ni1—N1—C12—C4	−177.28 (18)
N1—Ni1—N2—C11	3.16 (15)	C1—N1—C12—C11	−177.4 (2)
N1ⁱ—Ni1—N2—C11	−169.16 (16)	Ni1—N1—C12—C11	5.0 (2)
N2ⁱ—Ni1—N2—C11	−88.62 (15)	C3—C4—C12—N1	−0.2 (4)
O1ⁱ—Ni1—N2—C11	69.5 (3)	C5—C4—C12—N1	−178.1 (2)
O1—Ni1—N2—C11	98.00 (15)	C3—C4—C12—C11	177.5 (2)
C12—N1—C1—C2	−0.4 (4)	C5—C4—C12—C11	−0.4 (4)
Ni1—N1—C1—C2	176.71 (19)	N2—C11—C12—N1	−2.4 (3)
N1—C1—C2—C3	0.4 (4)	C7—C11—C12—N1	175.7 (2)
C1—C2—C3—C4	−0.3 (4)	N2—C11—C12—C4	179.8 (2)
C2—C3—C4—C12	0.2 (4)	C7—C11—C12—C4	−2.1 (3)
C2—C3—C4—C5	178.0 (3)

Symmetry code: (i) −x, y, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3B···O2	0.82	1.97	2.705 (6)	148
O3′—H3′A···O2	0.82	2.00	2.767 (8)	155

Selected bond lengths (Å) top

Ni1—N1	2.0762 (19)	S1—O2	1.4587 (17)
Ni1—N2	2.082 (2)	S1—O1	1.4942 (16)
Ni1—O1	2.1074 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3B···O2	0.82	1.97	2.705 (6)	148.4
O3'—H3'A···O2	0.82	2.00	2.767 (8)	154.8

Acknowledgements

This work was partially supported by the Scientific Research Foundation of Nanjing College of Chemical Technology (grant No. NHKY-2013-10)

References

Batten, S. R. & Robson, R. (1998). Chem. Commun. pp. 1067–1068. Google Scholar
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
Zhang, L.-P., Ma, J.-F., Yang, J., Pang, Y.-Y. & Ma, J.-C. (2010). Inorg. Chem. 49, 1535–1550. Web of Science CSD CrossRef CAS PubMed Google Scholar
Zhong, K.-L. (2013). Acta Cryst. E69, m26. CSD CrossRef IUCr Journals Google Scholar
Zhong, K.-L., Chen, L. & Chen, L. (2011). Acta Cryst. C67, m62–m64. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Zhong, K.-L. & Ni, C. (2012). Acta Cryst. E68, m1519. 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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