Bis(1,10-phenanthroline-κ(2) N,N')(sulfato-κ(2) O,O')nickel(II) propane-1,2-diol monosolvate.

In the title compound, [Ni(SO4)(C12H8N2)2]·C3H8O2, the Ni(II) atom exhibits a distorted octa-hedral 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 mol-ecule. 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 inter-molecular O-H⋯O hydrogen bonds involving the uncoordinating O atoms of the sulfate ion. Due to symmetry, the solvent mol-ecule 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 = 591.27

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.084

S = 1.01

2602 reflections

191 parameters

26 restraints

H-atom parameters constrained

Δρmax = 0.32 e Å−3

Δρmin = −0.42 e Å−3

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.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813023027/zq2207sup1.cif

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Ni(SO4)(C12H8N2)2]·C3H8O2	F(000) = 1224
Mr = 591.27	Dx = 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

Rigaku Mercury CCD diffractometer	2602 independent reflections
Radiation source: fine-focus sealed tube	2311 reflections with I > 2σ(I)
Graphite Monochromator monochromator	Rint = 0.031
Detector resolution: 28.5714 pixels mm-1	θmax = 26.4°, θmin = 3.1°
ω scans	h = −21→22
Absorption correction: multi-scan (REQAB; Jacobson, 1998)	k = −16→16
Tmin = 0.876, Tmax = 1.000	l = −16→14
7993 measured reflections

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(Fo2) + (0.0343P)2 + 4.7899P] where P = (Fo2 + 2Fc2)/3
2602 reflections	(Δ/σ)max < 0.001
191 parameters	Δρmax = 0.32 e Å−3
26 restraints	Δρmin = −0.42 e Å−3

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.

	x	y	z	Uiso*/Ueq	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

	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)

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)

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

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