Bis(2,2'-bipyridyl-κN,N')(sulfato-κO,O')zinc(II) ethane-1,2-diol solvate.

The title compound, [Zn(SO(4))(C(10)H(8)N(2))(2)]·C(2)H(6)O(2), is a six-coordinate zinc(II) complex with a distorted octa-hedral coordination geometry. The Zn(II) atom is bonded by two O atoms of the bidentate chelating sulfate ligand and four N atoms of the two chelating 2,2'-bipyridine ligands. The Zn-N bond distances range from 2.1287 (17) to 2.1452 (17) Å and the Zn-O bond distance is 2.1811 (15) Å. The two chelating NCCN groups subtend a dihedral angle of 81.1 (1)°. In the crystal structure, the [ZnSO(4)(C(10)H(8)N(2))(2)] and C(2)H(6)O(2) units are connected by inter-molecular O-H⋯O hydrogen bonding, which leads to additional stabilization of the structure.

Related literature

For related compounds, see: Liu & Arora (1993 ▶); Harvey et al. (2001 ▶, 2002 ▶); Jian et al. (2004 ▶); Rodrigues (2004 ▶); Juric et al. (2006 ▶); Zhu et al. (2006 ▶); Yu et al. (2007 ▶); Zhong et al. (2007 ▶).

Experimental

Crystal data

[Zn(SO4)(C10H8N2)2]·C2H6O2

M = 535.90

Monoclinic,

a = 17.017 (3) Å

b = 11.890 (2) Å

c = 12.831 (3) Å

β = 122.14 (3)°

V = 2198.3 (10) Å3

Z = 4

Mo Kα radiation

μ = 1.26 mm−1

T = 223 K

0.55 × 0.45 × 0.20 mm

Data collection

Rigaku Mercury CCD diffractometer

Absorption correction: multi-scan (REQAB; Jacobson, 1998 ▶) T min = 0.747, T max = 1.000

6138 measured reflections

2489 independent reflections

2155 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.088

S = 1.08

2489 reflections

156 parameters

H-atom parameters constrained

Δρmax = 0.66 e Å−3

Δρmin = −0.50 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 datablocks global, I. DOI: 10.1107/S1600536809055433/bq2188sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809055433/bq2188Isup2.hkl

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

[Zn(SO4)(C10H8N2)2]·C2H6O2	F(000) = 1104
Mr = 535.90	Dx = 1.619 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 5954 reflections
a = 17.017 (3) Å	θ = 3.4–27.5°
b = 11.890 (2) Å	µ = 1.26 mm−1
c = 12.831 (3) Å	T = 223 K
β = 122.14 (3)°	Prism, colorless
V = 2198.3 (10) Å3	0.55 × 0.45 × 0.20 mm
Z = 4

Rigaku Mercury CCD diffractometer	2489 independent reflections
Radiation source: fine-focus sealed tube	2155 reflections with I > 2σ(I)
Graphite Monochromator	Rint = 0.021
Detector resolution: 28.5714 pixels mm-1	θmax = 27.5°, θmin = 3.4°
ω scans	h = −22→22
Absorption correction: multi-scan (REQAB; Jacobson, 1998)	k = −12→15
Tmin = 0.747, Tmax = 1.000	l = −16→11
6138 measured reflections

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)] = 0.035	H-atom parameters constrained
wR(F2) = 0.088	w = 1/[σ2(Fo2) + (0.0539P)2] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max < 0.001
2489 reflections	Δρmax = 0.66 e Å−3
156 parameters	Δρmin = −0.50 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: 0.0173 (10)

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
Zn1	0.0000	0.30659 (2)	0.2500	0.02342 (14)
S1	0.0000	0.53723 (5)	0.2500	0.02518 (18)
N2	0.09876 (11)	0.19245 (12)	0.38322 (15)	0.0241 (4)
O1	−0.04900 (9)	0.46074 (12)	0.14153 (13)	0.0304 (3)
O2	0.06823 (10)	0.60723 (12)	0.24320 (15)	0.0359 (4)
C9	0.16178 (16)	0.07532 (17)	0.5611 (2)	0.0327 (5)
H9A	0.1567	0.0452	0.6242	0.039*
C7	0.24124 (14)	0.09388 (16)	0.45508 (19)	0.0280 (4)
H7A	0.2911	0.0771	0.4469	0.034*
C8	0.23603 (14)	0.04818 (17)	0.55093 (19)	0.0316 (5)
H8A	0.2821	−0.0001	0.6074	0.038*
C10	0.09473 (14)	0.14816 (18)	0.47609 (19)	0.0307 (4)
H10A	0.0450	0.1670	0.4839	0.037*
C6	0.17124 (13)	0.16470 (15)	0.37204 (18)	0.0233 (4)
N1	0.10086 (11)	0.29012 (13)	0.19914 (16)	0.0246 (4)
C5	0.17129 (13)	0.21769 (16)	0.26699 (18)	0.0234 (4)
C4	0.23903 (15)	0.19633 (16)	0.2402 (2)	0.0299 (4)
H4A	0.2869	0.1461	0.2880	0.036*
C1	0.09742 (14)	0.34294 (18)	0.1043 (2)	0.0297 (4)
H1A	0.0494	0.3935	0.0581	0.036*
C2	0.16244 (16)	0.32515 (18)	0.0724 (2)	0.0326 (5)
H2A	0.1578	0.3625	0.0057	0.039*
C3	0.23444 (15)	0.25072 (19)	0.1417 (2)	0.0336 (5)
H3A	0.2791	0.2374	0.1223	0.040*
O3	0.02134 (16)	0.82127 (14)	0.14925 (19)	0.0535 (5)
H3	0.0243	0.7602	0.1809	0.080*
C11	0.03464 (18)	0.90768 (19)	0.2313 (3)	0.0437 (6)
H11A	0.0316	0.9794	0.1934	0.052*
H11B	0.0963	0.9006	0.3045	0.052*

	U11	U22	U33	U12	U13	U23
Zn1	0.02046 (19)	0.0218 (2)	0.0288 (2)	0.000	0.01361 (15)	0.000
S1	0.0204 (3)	0.0203 (3)	0.0342 (4)	0.000	0.0141 (3)	0.000
N2	0.0227 (8)	0.0242 (8)	0.0248 (8)	−0.0007 (6)	0.0122 (7)	−0.0012 (6)
O1	0.0258 (7)	0.0285 (7)	0.0321 (8)	0.0005 (6)	0.0120 (6)	−0.0016 (6)
O2	0.0303 (8)	0.0280 (7)	0.0520 (10)	−0.0042 (6)	0.0236 (7)	0.0030 (7)
C9	0.0364 (11)	0.0338 (11)	0.0273 (11)	0.0006 (9)	0.0166 (9)	0.0038 (9)
C7	0.0228 (9)	0.0263 (10)	0.0312 (11)	0.0022 (8)	0.0118 (8)	−0.0011 (8)
C8	0.0284 (10)	0.0290 (10)	0.0289 (11)	0.0030 (9)	0.0094 (9)	0.0030 (8)
C10	0.0296 (10)	0.0346 (11)	0.0303 (10)	0.0027 (9)	0.0176 (9)	0.0011 (9)
C6	0.0223 (9)	0.0195 (8)	0.0256 (9)	−0.0022 (7)	0.0111 (8)	−0.0042 (7)
N1	0.0219 (8)	0.0242 (8)	0.0287 (9)	−0.0002 (7)	0.0140 (7)	0.0004 (7)
C5	0.0213 (9)	0.0208 (9)	0.0261 (9)	−0.0025 (7)	0.0112 (8)	−0.0037 (7)
C4	0.0256 (10)	0.0307 (10)	0.0348 (11)	0.0036 (8)	0.0170 (9)	−0.0013 (9)
C1	0.0292 (10)	0.0297 (10)	0.0327 (11)	0.0033 (9)	0.0182 (9)	0.0056 (9)
C2	0.0358 (11)	0.0344 (11)	0.0337 (11)	−0.0045 (9)	0.0227 (10)	−0.0008 (9)
C3	0.0323 (11)	0.0372 (12)	0.0396 (12)	−0.0011 (10)	0.0247 (10)	−0.0045 (10)
O3	0.0912 (15)	0.0382 (9)	0.0511 (11)	0.0008 (9)	0.0513 (11)	0.0052 (8)
C11	0.0494 (14)	0.0302 (11)	0.0551 (16)	−0.0024 (10)	0.0301 (13)	0.0025 (10)

Zn1—N2i	2.1287 (17)	C8—H8A	0.9300
Zn1—N2	2.1287 (17)	C10—H10A	0.9300
Zn1—N1	2.1452 (17)	C6—C5	1.488 (3)
Zn1—N1i	2.1452 (17)	N1—C1	1.343 (3)
Zn1—O1i	2.1811 (15)	N1—C5	1.351 (3)
Zn1—O1	2.1811 (15)	C5—C4	1.390 (3)
Zn1—S1	2.7424 (8)	C4—C3	1.385 (3)
S1—O2	1.4683 (15)	C4—H4A	0.9300
S1—O2i	1.4683 (14)	C1—C2	1.385 (3)
S1—O1	1.4915 (15)	C1—H1A	0.9300
S1—O1i	1.4915 (15)	C2—C3	1.384 (3)
N2—C10	1.338 (3)	C2—H2A	0.9300
N2—C6	1.356 (3)	C3—H3A	0.9300
C9—C8	1.376 (3)	O3—C11	1.401 (3)
C9—C10	1.385 (3)	O3—H3	0.8200
C9—H9A	0.9300	C11—C11i	1.490 (5)
C7—C6	1.383 (3)	C11—H11A	0.9700
C7—C8	1.390 (3)	C11—H11B	0.9700
C7—H7A	0.9300
N2i—Zn1—N2	100.78 (9)	C6—C7—C8	119.04 (19)
N2i—Zn1—N1	96.61 (7)	C6—C7—H7A	120.5
N2—Zn1—N1	76.61 (7)	C8—C7—H7A	120.5
N2i—Zn1—N1i	76.61 (7)	C9—C8—C7	119.1 (2)
N2—Zn1—N1i	96.61 (7)	C9—C8—H8A	120.4
N1—Zn1—N1i	169.52 (9)	C7—C8—H8A	120.4
N2i—Zn1—O1i	156.73 (6)	N2—C10—C9	122.5 (2)
N2—Zn1—O1i	98.79 (6)	N2—C10—H10A	118.8
N1—Zn1—O1i	100.06 (6)	C9—C10—H10A	118.8
N1i—Zn1—O1i	88.78 (6)	N2—C6—C7	121.72 (19)
N2i—Zn1—O1	98.79 (6)	N2—C6—C5	115.57 (17)
N2—Zn1—O1	156.73 (6)	C7—C6—C5	122.69 (18)
N1—Zn1—O1	88.78 (6)	C1—N1—C5	118.56 (17)
N1i—Zn1—O1	100.06 (6)	C1—N1—Zn1	125.22 (14)
O1i—Zn1—O1	65.64 (8)	C5—N1—Zn1	116.18 (13)
N2i—Zn1—S1	129.61 (4)	N1—C5—C4	121.68 (19)
N2—Zn1—S1	129.61 (4)	N1—C5—C6	115.19 (17)
N1—Zn1—S1	95.24 (4)	C4—C5—C6	123.12 (18)
N1i—Zn1—S1	95.24 (4)	C3—C4—C5	119.26 (19)
O1i—Zn1—S1	32.82 (4)	C3—C4—H4A	120.4
O1—Zn1—S1	32.82 (4)	C5—C4—H4A	120.4
O2—S1—O2i	110.95 (12)	N1—C1—C2	122.7 (2)
O2—S1—O1	110.94 (9)	N1—C1—H1A	118.7
O2i—S1—O1	109.50 (8)	C2—C1—H1A	118.7
O2—S1—O1i	109.50 (8)	C3—C2—C1	118.8 (2)
O2i—S1—O1i	110.94 (9)	C3—C2—H2A	120.6
O1—S1—O1i	104.85 (12)	C1—C2—H2A	120.6
O2—S1—Zn1	124.53 (6)	C2—C3—C4	119.0 (2)
O2i—S1—Zn1	124.53 (6)	C2—C3—H3A	120.5
O1—S1—Zn1	52.43 (6)	C4—C3—H3A	120.5
O1i—S1—Zn1	52.43 (6)	C11—O3—H3	109.5
C10—N2—C6	118.62 (17)	O3—C11—C11i	113.7 (2)
C10—N2—Zn1	125.01 (14)	O3—C11—H11A	108.8
C6—N2—Zn1	116.37 (13)	C11i—C11—H11A	108.8
S1—O1—Zn1	94.75 (8)	O3—C11—H11B	108.8
C8—C9—C10	119.0 (2)	C11i—C11—H11B	108.8
C8—C9—H9A	120.5	H11A—C11—H11B	107.7
C10—C9—H9A	120.5
N2i—Zn1—S1—O2	−114.55 (10)	N1i—Zn1—O1—S1	84.03 (8)
N2—Zn1—S1—O2	65.45 (10)	O1i—Zn1—O1—S1	0.0
N1—Zn1—S1—O2	−11.49 (9)	C10—C9—C8—C7	−0.5 (3)
N1i—Zn1—S1—O2	168.51 (9)	C6—C7—C8—C9	−0.5 (3)
O1i—Zn1—S1—O2	88.97 (11)	C6—N2—C10—C9	0.1 (3)
O1—Zn1—S1—O2	−91.03 (11)	Zn1—N2—C10—C9	−179.13 (15)
N2i—Zn1—S1—O2i	65.45 (10)	C8—C9—C10—N2	0.8 (3)
N2—Zn1—S1—O2i	−114.55 (10)	C10—N2—C6—C7	−1.2 (3)
N1—Zn1—S1—O2i	168.51 (9)	Zn1—N2—C6—C7	178.11 (14)
N1i—Zn1—S1—O2i	−11.49 (9)	C10—N2—C6—C5	−179.68 (17)
O1i—Zn1—S1—O2i	−91.03 (11)	Zn1—N2—C6—C5	−0.4 (2)
O1—Zn1—S1—O2i	88.97 (11)	C8—C7—C6—N2	1.4 (3)
N2i—Zn1—S1—O1	−23.52 (9)	C8—C7—C6—C5	179.77 (18)
N2—Zn1—S1—O1	156.48 (9)	N2i—Zn1—N1—C1	80.70 (17)
N1—Zn1—S1—O1	79.54 (9)	N2—Zn1—N1—C1	−179.74 (18)
N1i—Zn1—S1—O1	−100.46 (9)	N1i—Zn1—N1—C1	129.77 (17)
O1i—Zn1—S1—O1	180.0	O1i—Zn1—N1—C1	−83.00 (17)
N2i—Zn1—S1—O1i	156.48 (9)	O1—Zn1—N1—C1	−18.01 (17)
N2—Zn1—S1—O1i	−23.52 (9)	S1—Zn1—N1—C1	−50.23 (17)
N1—Zn1—S1—O1i	−100.46 (9)	N2i—Zn1—N1—C5	−97.15 (14)
N1i—Zn1—S1—O1i	79.54 (9)	N2—Zn1—N1—C5	2.41 (13)
O1—Zn1—S1—O1i	180.0	N1i—Zn1—N1—C5	−48.08 (13)
N2i—Zn1—N2—C10	−87.46 (16)	O1i—Zn1—N1—C5	99.15 (14)
N1—Zn1—N2—C10	178.23 (17)	O1—Zn1—N1—C5	164.14 (14)
N1i—Zn1—N2—C10	−9.89 (17)	S1—Zn1—N1—C5	131.92 (13)
O1i—Zn1—N2—C10	79.90 (16)	C1—N1—C5—C4	−0.5 (3)
O1—Zn1—N2—C10	125.73 (18)	Zn1—N1—C5—C4	177.47 (15)
S1—Zn1—N2—C10	92.54 (16)	C1—N1—C5—C6	178.66 (17)
N2i—Zn1—N2—C6	93.31 (13)	Zn1—N1—C5—C6	−3.3 (2)
N1—Zn1—N2—C6	−1.00 (13)	N2—C6—C5—N1	2.5 (2)
N1i—Zn1—N2—C6	170.88 (13)	C7—C6—C5—N1	−176.01 (17)
O1i—Zn1—N2—C6	−99.33 (13)	N2—C6—C5—C4	−178.35 (18)
O1—Zn1—N2—C6	−53.5 (2)	C7—C6—C5—C4	3.2 (3)
S1—Zn1—N2—C6	−86.69 (13)	N1—C5—C4—C3	0.1 (3)
O2—S1—O1—Zn1	118.12 (8)	C6—C5—C4—C3	−179.02 (18)
O2i—S1—O1—Zn1	−119.09 (8)	C5—N1—C1—C2	0.8 (3)
O1i—S1—O1—Zn1	0.0	Zn1—N1—C1—C2	−177.02 (15)
N2i—Zn1—O1—S1	161.88 (7)	N1—C1—C2—C3	−0.6 (3)
N2—Zn1—O1—S1	−51.09 (18)	C1—C2—C3—C4	0.1 (3)
N1—Zn1—O1—S1	−101.62 (8)	C5—C4—C3—C2	0.1 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O2	0.82	1.97	2.746 (2)	158

Zn1—N2	2.1287 (17)
Zn1—N1	2.1452 (17)
Zn1—O1	2.1811 (15)
S1—O2	1.4683 (15)
S1—O1	1.4915 (15)

N2—Zn1—N1	76.61 (7)
O1i—Zn1—O1	65.64 (8)

Symmetry code: (i) .

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O2	0.82	1.97	2.746 (2)	158