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

Zhong, K.-L.; Ni, C.; Wang, J.-M.

doi:10.1107/S1600536809026269

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

In the title compound, [Ni(SO₄)(C₁₂H₈N₂)₂]·C₂H₆O₂, the coordination polyhedron around the Ni²⁺ ion is a distorted octahedron, with four N atoms from two phenanthroline groups and two O atoms from a bidentate sulfate ligand. The Ni²⁺ ion lies on a special position of site symmetry 2. Intermolecular O—H

O hydrogen bonds help to stabilize the structure. The OH group of the ethane-1,2-diol solvent is disordered over two positions with equal occupancy.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536809026269/pk2166sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536809026269/pk2166Isup2.hkl Contains datablock I

CCDC reference: 744191

checkCIF report

Key indicators

Single-crystal X-ray study
T = 295 K
Mean (C-C) = 0.004 Å
Disorder in solvent or counterion
R factor = 0.036
wR factor = 0.106
Data-to-parameter ratio = 16.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbours of        O3'
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          2
              C2 H6 O2

Alert level G
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......         17
PLAT062_ALERT_4_G Rescale T(min) & T(max) by .....................       0.99
PLAT302_ALERT_4_G Note Anion/Solvent Disorder ....................      33.00 Perc.
PLAT710_ALERT_4_G Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         31
            N1  -NI1 -N1  -C1   -126.00  0.20   2.556   1.555   1.555   1.555
PLAT710_ALERT_4_G Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         37
            N1  -NI1 -N1  -C5     54.20  0.14   2.556   1.555   1.555   1.555
PLAT779_ALERT_4_G Suspect or Irrelevant (Bond) Angle in CIF ......      35.70 Deg.
              O3   -C13  -O3'     1.555   1.555   1.555

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   6 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   7 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

Ni-phen (phen = phenanthroline) complexes with chloride-anion and water-molecule ligands have been synthesized and characterized by X-ray diffraction (Chen et al., 2005; Su & Xu, 2005; Tang et al., 2007). The title nickel complex [NiSO₄(phen)₂].C₂H₆O₂, Fig. 1, is isostructural to the recently reported cobalt(II) and cadmium(II) analogs (Zhong et al., 2006; Lu et al., 2006). A twofold rotation axis passes through the Ni and S atoms, and also through the mid-point of the C—C bond of the solvent molcule. The Ni^II center has an octahedral geometry, with four N atoms from two phen groups and two O atoms from a bidentate sulfate ligand. The geometry of the phen and sulfate ligands are in good agreement with those reported in the two isomorphous complexes [ZnSO₄(phen)₂].C₂H₆O₂ and [MnSO₄(phen)₂].C₂H₆O₂ (Zhu et al., 2006a,b).

The ethane-1,2-diol solvent is disordered over two positions, and is hydrogen bonded to the sulfate ligand (Table 1).

Related literature top

For Ni–phen complexes with chloride anions and water molecules as a second ligand, see: Chen et al. (2005); Su & Xu (2005); Tang et al. (2007). For isomorphous analogs, see: Zhong et al. (2006); Lu et al. (2006); Zhu et al. (2006a,b).

Experimental top

Green block-shaped crystals of the title compound were obtained by a procedure similar to that described previously (Zhong et al., 2006), but with NiSO₄.7H₂O in place of CoSO₄.7H₂O.

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell refinement: CrysAlis PRO (Oxford Diffraction, 2009); data reduction: CrysAlis PRO (Oxford Diffraction, 2009); 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 50% probability level. The dashed lines represent O—H···O interactions. Unlabeled atoms are related to the labelled atoms by the symmetry operator (-x, y, -z +3/2). Only one disorder component is shown.

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

Crystal data top

[Ni(SO₄)(C₁₂H₈N₂)₂]·C₂H₆O₂	F(000) = 1192
M_r = 577.25	D_x = 1.567 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 6902 reflections
a = 18.4551 (9) Å	θ = 3.2–30.6°
b = 11.8839 (5) Å	µ = 0.93 mm⁻¹
c = 12.7526 (6) Å	T = 295 K
β = 118.991 (6)°	Block, green
V = 2446.4 (2) Å³	0.36 × 0.33 × 0.28 mm
Z = 4

Data collection top

Oxford Diffraction Gemini S Ultra diffractometer	3010 independent reflections
Radiation source: fine-focus sealed tube	2467 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
Detector resolution: 8.1241 pixels mm^-1	θ_max = 28.3°, θ_min = 3.2°
ϕ and ω scans	h = −24→24
Absorption correction: multi-scan (ABSPACK; Oxford Diffraction, 2009)	k = −15→15
T_min = 0.731, T_max = 0.781	l = −17→16
11586 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)] = 0.036	H-atom parameters constrained
wR(F²) = 0.106	w = 1/[σ²(F_o²) + (0.0643P)² + 0.296P] where P = (F_o² + 2F_c²)/3
S = 1.08	(Δ/σ)_max < 0.001
3010 reflections	Δρ_max = 0.35 e Å⁻³
183 parameters	Δρ_min = −0.52 e Å⁻³
17 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: 0.0055 (6)

Crystal data top

[Ni(SO₄)(C₁₂H₈N₂)₂]·C₂H₆O₂	V = 2446.4 (2) Å³
M_r = 577.25	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 18.4551 (9) Å	µ = 0.93 mm⁻¹
b = 11.8839 (5) Å	T = 295 K
c = 12.7526 (6) Å	0.36 × 0.33 × 0.28 mm
β = 118.991 (6)°

Data collection top

Oxford Diffraction Gemini S Ultra diffractometer	3010 independent reflections
Absorption correction: multi-scan (ABSPACK; Oxford Diffraction, 2009)	2467 reflections with I > 2σ(I)
T_min = 0.731, T_max = 0.781	R_int = 0.029
11586 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	17 restraints
wR(F²) = 0.106	H-atom parameters constrained
S = 1.08	Δρ_max = 0.35 e Å⁻³
3010 reflections	Δρ_min = −0.52 e Å⁻³
183 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	0.19859 (3)	0.7500	0.02868 (15)
S1	0.0000	−0.02657 (6)	0.7500	0.02857 (19)
O2	−0.05633 (9)	0.05119 (13)	0.65249 (13)	0.0379 (4)
O1	0.04687 (11)	−0.09628 (15)	0.71006 (17)	0.0479 (5)
N1	0.07956 (11)	0.21105 (15)	0.67829 (16)	0.0314 (4)
N2	0.08892 (12)	0.30656 (14)	0.87419 (16)	0.0331 (4)
C5	0.14702 (13)	0.27545 (18)	0.74544 (17)	0.0291 (4)
C7	0.28779 (15)	0.4016 (2)	0.8974 (2)	0.0438 (6)
H7	0.3347	0.4428	0.9481	0.053*
C9	0.22836 (17)	0.4292 (2)	1.0353 (2)	0.0458 (6)
H9	0.2743	0.4702	1.0893	0.055*
C4	0.21016 (14)	0.2934 (2)	0.7163 (2)	0.0368 (5)
C8	0.22400 (15)	0.38596 (19)	0.92872 (19)	0.0368 (5)
C12	0.15344 (13)	0.32477 (17)	0.85260 (18)	0.0303 (5)
C6	0.28132 (15)	0.3577 (2)	0.7956 (2)	0.0454 (6)
H6	0.3236	0.3694	0.7769	0.055*
C1	0.07228 (15)	0.1648 (2)	0.5783 (2)	0.0391 (5)
H1	0.0260	0.1209	0.5310	0.047*
C2	0.13218 (17)	0.1802 (2)	0.5424 (2)	0.0474 (6)
H2	0.1250	0.1481	0.4715	0.057*
C3	0.20060 (16)	0.2421 (2)	0.6110 (2)	0.0475 (6)
H3	0.2413	0.2506	0.5885	0.057*
C10	0.16452 (19)	0.4099 (2)	1.0571 (2)	0.0507 (7)
H10	0.1667	0.4375	1.1268	0.061*
C11	0.09572 (16)	0.3488 (2)	0.9757 (2)	0.0428 (6)
H11	0.0527	0.3369	0.9927	0.051*
C13	0.0291 (3)	−0.4047 (3)	0.7245 (4)	0.0978 (14)
H13A	0.0809	−0.4351	0.7869	0.117*
H13B	0.0073	−0.4600	0.6606	0.117*
O3	0.0492 (5)	−0.3177 (5)	0.6817 (6)	0.098 (2)	0.50
H3A	0.0752	−0.2727	0.7359	0.147*	0.50
O3'	0.0850 (3)	−0.3224 (4)	0.7512 (6)	0.0726 (17)	0.50
H3'	0.0792	−0.2939	0.6891	0.109*	0.50

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.0250 (2)	0.0289 (2)	0.0293 (2)	0.000	0.01088 (16)	0.000
S1	0.0222 (3)	0.0282 (4)	0.0318 (4)	0.000	0.0103 (3)	0.000
O2	0.0302 (8)	0.0346 (9)	0.0318 (8)	−0.0013 (7)	0.0014 (6)	−0.0005 (6)
O1	0.0430 (10)	0.0455 (11)	0.0622 (11)	0.0066 (8)	0.0310 (9)	−0.0055 (8)
N1	0.0282 (9)	0.0318 (10)	0.0304 (9)	−0.0019 (8)	0.0111 (7)	−0.0032 (7)
N2	0.0377 (10)	0.0293 (10)	0.0325 (9)	−0.0029 (8)	0.0172 (8)	−0.0026 (7)
C5	0.0266 (10)	0.0280 (11)	0.0282 (9)	0.0013 (8)	0.0097 (8)	0.0015 (8)
C7	0.0300 (12)	0.0428 (15)	0.0448 (13)	−0.0097 (10)	0.0072 (10)	−0.0017 (10)
C9	0.0495 (15)	0.0406 (14)	0.0351 (12)	−0.0087 (12)	0.0109 (11)	−0.0088 (10)
C4	0.0307 (11)	0.0397 (13)	0.0387 (12)	−0.0003 (10)	0.0157 (9)	0.0034 (9)
C8	0.0375 (12)	0.0297 (12)	0.0326 (11)	−0.0042 (10)	0.0088 (9)	−0.0003 (9)
C12	0.0300 (11)	0.0267 (11)	0.0278 (10)	−0.0001 (8)	0.0091 (8)	0.0013 (8)
C6	0.0295 (11)	0.0544 (17)	0.0491 (14)	−0.0070 (12)	0.0164 (10)	0.0007 (12)
C1	0.0381 (12)	0.0429 (13)	0.0336 (11)	−0.0037 (11)	0.0154 (10)	−0.0085 (9)
C2	0.0504 (15)	0.0572 (17)	0.0388 (13)	−0.0021 (13)	0.0248 (12)	−0.0087 (11)
C3	0.0428 (14)	0.0621 (18)	0.0453 (13)	−0.0046 (13)	0.0275 (12)	−0.0026 (12)
C10	0.0664 (18)	0.0476 (16)	0.0360 (12)	−0.0080 (13)	0.0231 (12)	−0.0121 (11)
C11	0.0522 (15)	0.0417 (14)	0.0386 (12)	−0.0074 (12)	0.0252 (11)	−0.0086 (10)
C13	0.111 (3)	0.066 (2)	0.141 (3)	0.002 (2)	0.081 (3)	−0.002 (2)
O3	0.130 (5)	0.087 (4)	0.115 (4)	0.009 (3)	0.090 (4)	0.017 (3)
O3'	0.061 (3)	0.042 (3)	0.129 (5)	0.017 (2)	0.056 (3)	0.028 (3)

Geometric parameters (Å, º) top

Ni1—N1ⁱ	2.0774 (18)	C9—C8	1.418 (3)
Ni1—N1	2.0774 (18)	C9—H9	0.9300
Ni1—N2	2.0805 (19)	C4—C3	1.406 (3)
Ni1—N2ⁱ	2.0805 (18)	C4—C6	1.430 (3)
Ni1—O2	2.1077 (16)	C8—C12	1.393 (3)
Ni1—O2ⁱ	2.1077 (16)	C6—H6	0.9300
Ni1—S1	2.6757 (8)	C1—C2	1.398 (3)
S1—O1ⁱ	1.4563 (17)	C1—H1	0.9300
S1—O1	1.4563 (17)	C2—C3	1.352 (4)
S1—O2ⁱ	1.4926 (16)	C2—H2	0.9300
S1—O2	1.4926 (16)	C3—H3	0.9300
N1—C1	1.334 (3)	C10—C11	1.392 (4)
N1—C5	1.355 (3)	C10—H10	0.9300
N2—C11	1.337 (3)	C11—H11	0.9300
N2—C12	1.363 (3)	C13—O3	1.304 (5)
C5—C4	1.401 (3)	C13—O3'	1.339 (5)
C5—C12	1.438 (3)	C13—C13ⁱ	1.501 (4)
C7—C6	1.349 (4)	C13—H13A	0.9700
C7—C8	1.427 (4)	C13—H13B	0.9700
C7—H7	0.9300	O3—H3A	0.8200
C9—C10	1.355 (4)	O3'—H3'	0.8200

N1ⁱ—Ni1—N1	171.82 (10)	C8—C7—H7	119.4
N1ⁱ—Ni1—N2	94.93 (7)	C10—C9—C8	119.0 (2)
N1—Ni1—N2	79.99 (7)	C10—C9—H9	120.5
N1ⁱ—Ni1—N2ⁱ	79.99 (7)	C8—C9—H9	120.5
N1—Ni1—N2ⁱ	94.93 (7)	C5—C4—C3	116.9 (2)
N2—Ni1—N2ⁱ	103.84 (10)	C5—C4—C6	119.4 (2)
N1ⁱ—Ni1—O2	93.85 (7)	C3—C4—C6	123.7 (2)
N1—Ni1—O2	92.94 (7)	C12—C8—C9	117.2 (2)
N2—Ni1—O2	160.60 (7)	C12—C8—C7	119.5 (2)
N2ⁱ—Ni1—O2	94.70 (6)	C9—C8—C7	123.3 (2)
N1ⁱ—Ni1—O2ⁱ	92.94 (7)	N2—C12—C8	123.7 (2)
N1—Ni1—O2ⁱ	93.85 (7)	N2—C12—C5	116.71 (19)
N2—Ni1—O2ⁱ	94.70 (6)	C8—C12—C5	119.6 (2)
N2ⁱ—Ni1—O2ⁱ	160.60 (7)	C7—C6—C4	120.7 (2)
O2—Ni1—O2ⁱ	67.58 (8)	C7—C6—H6	119.7
N1ⁱ—Ni1—S1	94.09 (5)	C4—C6—H6	119.7
N1—Ni1—S1	94.09 (5)	N1—C1—C2	122.0 (2)
N2—Ni1—S1	128.08 (5)	N1—C1—H1	119.0
N2ⁱ—Ni1—S1	128.08 (5)	C2—C1—H1	119.0
O2—Ni1—S1	33.79 (4)	C3—C2—C1	119.9 (2)
O2ⁱ—Ni1—S1	33.79 (4)	C3—C2—H2	120.1
O1ⁱ—S1—O1	110.66 (15)	C1—C2—H2	120.1
O1ⁱ—S1—O2ⁱ	110.65 (10)	C2—C3—C4	119.9 (2)
O1—S1—O2ⁱ	110.59 (10)	C2—C3—H3	120.0
O1ⁱ—S1—O2	110.59 (10)	C4—C3—H3	120.0
O1—S1—O2	110.65 (10)	C9—C10—C11	120.3 (2)
O2ⁱ—S1—O2	103.50 (13)	C9—C10—H10	119.9
O1ⁱ—S1—Ni1	124.67 (8)	C11—C10—H10	119.9
O1—S1—Ni1	124.67 (8)	N2—C11—C10	122.8 (2)
O2ⁱ—S1—Ni1	51.75 (6)	N2—C11—H11	118.6
O2—S1—Ni1	51.75 (6)	C10—C11—H11	118.6
S1—O2—Ni1	94.46 (7)	O3—C13—O3'	35.7 (4)
C1—N1—C5	118.22 (19)	O3—C13—C13ⁱ	126.2 (4)
C1—N1—Ni1	128.76 (16)	O3'—C13—C13ⁱ	121.0 (4)
C5—N1—Ni1	113.02 (13)	O3—C13—H13A	105.8
C11—N2—C12	117.1 (2)	O3'—C13—H13A	74.5
C11—N2—Ni1	129.66 (16)	C13ⁱ—C13—H13A	105.8
C12—N2—Ni1	112.83 (14)	O3—C13—H13B	105.8
N1—C5—C4	123.10 (19)	O3'—C13—H13B	131.5
N1—C5—C12	117.27 (18)	C13ⁱ—C13—H13B	105.8
C4—C5—C12	119.6 (2)	H13A—C13—H13B	106.2
C6—C7—C8	121.2 (2)	C13—O3—H3A	109.5
C6—C7—H7	119.4	C13—O3'—H3'	109.5

N1ⁱ—Ni1—S1—O1ⁱ	0.87 (10)	O2ⁱ—Ni1—N2—C11	−82.5 (2)
N1—Ni1—S1—O1ⁱ	−179.13 (10)	S1—Ni1—N2—C11	−88.3 (2)
N2—Ni1—S1—O1ⁱ	100.39 (11)	N1ⁱ—Ni1—N2—C12	−177.26 (15)
N2ⁱ—Ni1—S1—O1ⁱ	−79.61 (11)	N1—Ni1—N2—C12	−3.72 (14)
O2—Ni1—S1—O1ⁱ	−89.95 (12)	N2ⁱ—Ni1—N2—C12	−96.38 (15)
O2ⁱ—Ni1—S1—O1ⁱ	90.05 (12)	O2—Ni1—N2—C12	66.1 (3)
N1ⁱ—Ni1—S1—O1	−179.13 (10)	O2ⁱ—Ni1—N2—C12	89.37 (15)
N1—Ni1—S1—O1	0.87 (10)	S1—Ni1—N2—C12	83.62 (15)
N2—Ni1—S1—O1	−79.61 (11)	C1—N1—C5—C4	−1.6 (3)
N2ⁱ—Ni1—S1—O1	100.39 (11)	Ni1—N1—C5—C4	178.30 (17)
O2—Ni1—S1—O1	90.05 (12)	C1—N1—C5—C12	179.8 (2)
O2ⁱ—Ni1—S1—O1	−89.95 (12)	Ni1—N1—C5—C12	−0.3 (2)
N1ⁱ—Ni1—S1—O2ⁱ	−89.18 (9)	N1—C5—C4—C3	0.8 (3)
N1—Ni1—S1—O2ⁱ	90.82 (9)	C12—C5—C4—C3	179.4 (2)
N2—Ni1—S1—O2ⁱ	10.34 (10)	N1—C5—C4—C6	−176.7 (2)
N2ⁱ—Ni1—S1—O2ⁱ	−169.66 (10)	C12—C5—C4—C6	1.9 (3)
O2—Ni1—S1—O2ⁱ	180.0	C10—C9—C8—C12	−0.4 (4)
N1ⁱ—Ni1—S1—O2	90.82 (9)	C10—C9—C8—C7	−180.0 (2)
N1—Ni1—S1—O2	−89.18 (9)	C6—C7—C8—C12	−0.3 (4)
N2—Ni1—S1—O2	−169.66 (10)	C6—C7—C8—C9	179.2 (3)
N2ⁱ—Ni1—S1—O2	10.34 (10)	C11—N2—C12—C8	−1.3 (3)
O2ⁱ—Ni1—S1—O2	180.0	Ni1—N2—C12—C8	−174.28 (17)
O1ⁱ—S1—O2—Ni1	118.53 (10)	C11—N2—C12—C5	177.7 (2)
O1—S1—O2—Ni1	−118.49 (9)	Ni1—N2—C12—C5	4.7 (2)
O2ⁱ—S1—O2—Ni1	0.0	C9—C8—C12—N2	1.2 (3)
N1ⁱ—Ni1—O2—S1	−91.59 (8)	C7—C8—C12—N2	−179.2 (2)
N1—Ni1—O2—S1	92.96 (8)	C9—C8—C12—C5	−177.8 (2)
N2—Ni1—O2—S1	25.2 (2)	C7—C8—C12—C5	1.8 (3)
N2ⁱ—Ni1—O2—S1	−171.85 (8)	N1—C5—C12—N2	−3.0 (3)
O2ⁱ—Ni1—O2—S1	0.0	C4—C5—C12—N2	178.32 (19)
N1ⁱ—Ni1—N1—C1	−126.0 (2)	N1—C5—C12—C8	176.05 (19)
N2—Ni1—N1—C1	−178.0 (2)	C4—C5—C12—C8	−2.6 (3)
N2ⁱ—Ni1—N1—C1	−74.8 (2)	C8—C7—C6—C4	−0.4 (4)
O2—Ni1—N1—C1	20.2 (2)	C5—C4—C6—C7	−0.4 (4)
O2ⁱ—Ni1—N1—C1	87.9 (2)	C3—C4—C6—C7	−177.7 (3)
S1—Ni1—N1—C1	54.0 (2)	C5—N1—C1—C2	0.6 (4)
N1ⁱ—Ni1—N1—C5	54.20 (14)	Ni1—N1—C1—C2	−179.27 (19)
N2—Ni1—N1—C5	2.17 (14)	N1—C1—C2—C3	1.2 (4)
N2ⁱ—Ni1—N1—C5	105.39 (15)	C1—C2—C3—C4	−1.9 (4)
O2—Ni1—N1—C5	−159.64 (15)	C5—C4—C3—C2	1.0 (4)
O2ⁱ—Ni1—N1—C5	−91.93 (15)	C6—C4—C3—C2	178.3 (3)
S1—Ni1—N1—C5	−125.80 (14)	C8—C9—C10—C11	−0.3 (4)
N1ⁱ—Ni1—N2—C11	10.8 (2)	C12—N2—C11—C10	0.5 (4)
N1—Ni1—N2—C11	−175.6 (2)	Ni1—N2—C11—C10	172.17 (19)
N2ⁱ—Ni1—N2—C11	91.7 (2)	C9—C10—C11—N2	0.2 (4)
O2—Ni1—N2—C11	−105.8 (3)

Symmetry code: (i) −x, y, −z+3/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···O1	0.82	2.15	2.659 (7)	121
O3′—H3′···O1	0.82	2.47	2.763 (5)	102

Experimental details

Crystal data
Chemical formula	[Ni(SO₄)(C₁₂H₈N₂)₂]·C₂H₆O₂
M_r	577.25
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	295
a, b, c (Å)	18.4551 (9), 11.8839 (5), 12.7526 (6)
β (°)	118.991 (6)
V (Å³)	2446.4 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.93
Crystal size (mm)	0.36 × 0.33 × 0.28

Data collection
Diffractometer	Oxford Diffraction Gemini S Ultra diffractometer
Absorption correction	Multi-scan (ABSPACK; Oxford Diffraction, 2009)
T_min, T_max	0.731, 0.781
No. of measured, independent and observed [I > 2σ(I)] reflections	11586, 3010, 2467
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.106, 1.08
No. of reflections	3010
No. of parameters	183
No. of restraints	17
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.35, −0.52

Computer programs: CrysAlis PRO (Oxford Diffraction, 2009), 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···O1	0.82	2.15	2.659 (7)	120.6
O3'—H3'···O1	0.82	2.47	2.763 (5)	102.3

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