Bis[2-(2-pyridylmethyl-eneamino)benzene-sulfonato-κN,N',O]zinc(II) dihydrate.

In the title complex, [Zn(C(12)H(9)N(2)O(3)S)(2)]·2H(2)O, the Zn(II) ion lies on a crystallographic inversion center and is coordinated by four N atoms and two O atoms from two tridentate 2-(2-pyridylmethyl-eneamino)benzene-sulfonate ligands in a slightly distorted octa-hedral environment. In the crystal structure, the complex forms a two-dimensional network through inter-molecular O-H⋯O and C-H⋯O hydrogen bonds.

Related literature

For related literature, see: Casella & Gullotti (1981 ▶, 1986 ▶); Jiang et al. (2006 ▶); Li et al. (2006 ▶, 2007 ▶); Wang et al. (1994 ▶); Zhang et al. (2004 ▶, 2007 ▶, 2008 ▶); Correia et al. (2003 ▶); Zheng et al. (2001 ▶); Zhou et al. (2004 ▶).

Experimental

Crystal data

[Zn(C12H9N2O3S)2]·2H2O

M = 623.95

Orthorhombic,

a = 19.7090 (15) Å

b = 8.0722 (6) Å

c = 16.3390 (13) Å

V = 2599.5 (3) Å3

Z = 4

Mo Kα radiation

μ = 1.16 mm−1

T = 295 (2) K

0.49 × 0.45 × 0.37 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.600, T max = 0.673

17894 measured reflections

2412 independent reflections

2100 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.026

wR(F 2) = 0.074

S = 1.04

2412 reflections

177 parameters

H-atom parameters constrained

Δρmax = 0.46 e Å−3

Δρmin = −0.42 e Å−3

Data collection: SMART (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808026342/pk2112sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808026342/pk2112Isup2.hkl

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

[Zn(C12H9N2O3S1)2]·2H2O	F000 = 1280
Mr = 623.95	Dx = 1.594 Mg m−3
Orthorhombic, Pbcn	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 7323 reflections
a = 19.7090 (15) Å	θ = 2.5–28.2º
b = 8.0722 (6) Å	µ = 1.16 mm−1
c = 16.3390 (13) Å	T = 295 (2) K
V = 2599.5 (3) Å3	Block, yellow
Z = 4	0.49 × 0.45 × 0.37 mm

Bruker SMART CCD area-detector diffractometer	2412 independent reflections
Radiation source: fine-focus sealed tube	2100 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.024
T = 295(2) K	θmax = 25.5º
φ and ω scans	θmin = 2.5º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −23→23
Tmin = 0.600, Tmax = 0.673	k = −9→9
17894 measured reflections	l = −19→19

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)] = 0.026	H-atom parameters constrained
wR(F2) = 0.074	w = 1/[σ2(Fo2) + (0.0373P)2 + 1.7627P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
2412 reflections	Δρmax = 0.46 e Å−3
177 parameters	Δρmin = −0.42 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.5000	0.82446 (4)	0.2500	0.02769 (11)
S1	0.37616 (2)	0.67719 (6)	0.34320 (3)	0.03070 (14)
O1	0.45098 (7)	0.67650 (18)	0.33822 (8)	0.0344 (3)
O2	0.34865 (8)	0.84229 (19)	0.33446 (10)	0.0456 (4)
O3	0.35256 (7)	0.5876 (2)	0.41443 (8)	0.0431 (4)
N1	0.49613 (8)	1.0216 (2)	0.16032 (10)	0.0341 (4)
N2	0.40820 (8)	0.7687 (2)	0.17245 (9)	0.0297 (4)
C1	0.44459 (10)	1.0145 (3)	0.10605 (12)	0.0332 (4)
C2	0.43673 (13)	1.1301 (3)	0.04460 (14)	0.0452 (6)
H2	0.4007	1.1223	0.0081	0.054*
C3	0.48322 (13)	1.2579 (3)	0.03809 (15)	0.0506 (6)
H3	0.4786	1.3380	−0.0025	0.061*
C4	0.53638 (13)	1.2645 (3)	0.09261 (15)	0.0483 (6)
H4	0.5688	1.3480	0.0890	0.058*
C5	0.54084 (12)	1.1447 (3)	0.15295 (14)	0.0420 (5)
H5	0.5766	1.1503	0.1900	0.050*
C6	0.39854 (10)	0.8728 (3)	0.11481 (12)	0.0354 (5)
H6	0.3626	0.8590	0.0786	0.042*
C7	0.36755 (9)	0.6238 (3)	0.17777 (12)	0.0313 (4)
C8	0.34696 (11)	0.5353 (3)	0.10925 (13)	0.0437 (5)
H8	0.3579	0.5736	0.0572	0.052*
C9	0.31015 (12)	0.3900 (3)	0.11817 (15)	0.0524 (6)
H9	0.2962	0.3320	0.0720	0.063*
C10	0.29391 (13)	0.3306 (3)	0.19512 (16)	0.0516 (6)
H10	0.2698	0.2322	0.2005	0.062*
C11	0.31364 (11)	0.4180 (3)	0.26416 (13)	0.0403 (5)
H11	0.3022	0.3792	0.3160	0.048*
C12	0.35039 (10)	0.5632 (3)	0.25581 (11)	0.0300 (4)
O4	0.29845 (11)	1.0939 (4)	0.44343 (14)	0.1079 (10)
H1W	0.2572	1.1144	0.4394	0.162*
H2W	0.3083	1.0105	0.4158	0.162*

	U11	U22	U33	U12	U13	U23
Zn1	0.02732 (18)	0.03263 (19)	0.02311 (18)	0.000	−0.00389 (11)	0.000
S1	0.0291 (3)	0.0396 (3)	0.0234 (2)	−0.0001 (2)	0.00018 (18)	−0.0016 (2)
O1	0.0287 (7)	0.0462 (9)	0.0285 (7)	−0.0028 (6)	−0.0034 (6)	0.0038 (6)
O2	0.0482 (9)	0.0452 (9)	0.0436 (9)	0.0102 (7)	−0.0018 (7)	−0.0079 (7)
O3	0.0416 (8)	0.0620 (10)	0.0257 (7)	−0.0062 (8)	0.0039 (6)	0.0035 (7)
N1	0.0400 (9)	0.0346 (9)	0.0278 (9)	−0.0007 (7)	−0.0057 (7)	0.0011 (7)
N2	0.0278 (8)	0.0375 (9)	0.0238 (8)	−0.0006 (7)	0.0004 (6)	0.0004 (7)
C1	0.0343 (10)	0.0377 (11)	0.0275 (10)	0.0035 (9)	−0.0036 (8)	0.0023 (8)
C2	0.0519 (14)	0.0471 (13)	0.0367 (12)	0.0017 (11)	−0.0113 (10)	0.0096 (10)
C3	0.0728 (17)	0.0386 (13)	0.0403 (13)	−0.0023 (12)	−0.0064 (12)	0.0105 (11)
C4	0.0628 (15)	0.0363 (12)	0.0458 (13)	−0.0117 (11)	−0.0019 (11)	0.0022 (10)
C5	0.0490 (13)	0.0391 (12)	0.0380 (12)	−0.0084 (10)	−0.0102 (10)	0.0012 (9)
C6	0.0310 (11)	0.0475 (12)	0.0276 (10)	0.0001 (9)	−0.0057 (8)	0.0034 (9)
C7	0.0245 (10)	0.0410 (11)	0.0284 (10)	−0.0009 (8)	−0.0004 (8)	−0.0015 (9)
C8	0.0417 (12)	0.0609 (15)	0.0286 (11)	−0.0085 (11)	0.0014 (9)	−0.0050 (10)
C9	0.0505 (14)	0.0679 (16)	0.0389 (13)	−0.0180 (13)	−0.0001 (11)	−0.0169 (12)
C10	0.0464 (14)	0.0552 (15)	0.0530 (15)	−0.0211 (12)	0.0021 (11)	−0.0085 (12)
C11	0.0363 (12)	0.0495 (13)	0.0351 (11)	−0.0088 (10)	0.0038 (9)	0.0017 (10)
C12	0.0232 (9)	0.0399 (11)	0.0270 (10)	−0.0007 (8)	−0.0001 (7)	−0.0023 (8)
O4	0.0592 (13)	0.168 (3)	0.0964 (18)	0.0323 (15)	−0.0209 (12)	−0.0725 (19)

Zn1—O1	2.1065 (14)	C3—C4	1.376 (3)
Zn1—O1i	2.1065 (14)	C3—H3	0.9300
Zn1—N1i	2.1643 (18)	C4—C5	1.384 (3)
Zn1—N1	2.1643 (18)	C4—H4	0.9300
Zn1—N2	2.2544 (16)	C5—H5	0.9300
Zn1—N2i	2.2544 (16)	C6—H6	0.9300
S1—O2	1.4459 (16)	C7—C8	1.389 (3)
S1—O3	1.4470 (15)	C7—C12	1.407 (3)
S1—O1	1.4769 (14)	C8—C9	1.387 (3)
S1—C12	1.7730 (19)	C8—H8	0.9300
N1—C5	1.334 (3)	C9—C10	1.383 (3)
N1—C1	1.350 (2)	C9—H9	0.9300
N2—C6	1.277 (3)	C10—C11	1.386 (3)
N2—C7	1.421 (3)	C10—H10	0.9300
C1—C2	1.380 (3)	C11—C12	1.384 (3)
C1—C6	1.467 (3)	C11—H11	0.9300
C2—C3	1.384 (3)	O4—H1W	0.8332
C2—H2	0.9300	O4—H2W	0.8339
O1—Zn1—O1i	110.92 (8)	C3—C2—H2	120.5
O1—Zn1—N1i	88.27 (6)	C4—C3—C2	118.9 (2)
O1i—Zn1—N1i	149.76 (6)	C4—C3—H3	120.6
O1—Zn1—N1	149.76 (6)	C2—C3—H3	120.6
O1i—Zn1—N1	88.27 (6)	C3—C4—C5	118.9 (2)
N1i—Zn1—N1	85.36 (9)	C3—C4—H4	120.6
O1—Zn1—N2	84.45 (5)	C5—C4—H4	120.6
O1i—Zn1—N2	82.55 (5)	N1—C5—C4	122.9 (2)
N1i—Zn1—N2	123.75 (6)	N1—C5—H5	118.5
N1—Zn1—N2	74.81 (6)	C4—C5—H5	118.5
O1—Zn1—N2i	82.55 (5)	N2—C6—C1	119.53 (18)
O1i—Zn1—N2i	84.45 (5)	N2—C6—H6	120.2
N1i—Zn1—N2i	74.81 (6)	C1—C6—H6	120.2
N1—Zn1—N2i	123.75 (6)	C8—C7—C12	118.80 (19)
N2—Zn1—N2i	156.97 (9)	C8—C7—N2	122.62 (18)
O2—S1—O3	114.81 (10)	C12—C7—N2	118.51 (17)
O2—S1—O1	111.87 (9)	C9—C8—C7	120.2 (2)
O3—S1—O1	111.31 (9)	C9—C8—H8	119.9
O2—S1—C12	106.94 (9)	C7—C8—H8	119.9
O3—S1—C12	107.23 (9)	C10—C9—C8	120.7 (2)
O1—S1—C12	103.86 (9)	C10—C9—H9	119.7
S1—O1—Zn1	119.57 (8)	C8—C9—H9	119.7
C5—N1—C1	118.00 (18)	C9—C10—C11	119.9 (2)
C5—N1—Zn1	125.86 (14)	C9—C10—H10	120.1
C1—N1—Zn1	116.11 (14)	C11—C10—H10	120.1
C6—N2—C7	120.22 (17)	C12—C11—C10	119.8 (2)
C6—N2—Zn1	113.76 (14)	C12—C11—H11	120.1
C7—N2—Zn1	125.63 (12)	C10—C11—H11	120.1
N1—C1—C2	122.3 (2)	C11—C12—C7	120.62 (18)
N1—C1—C6	115.76 (17)	C11—C12—S1	120.65 (15)
C2—C1—C6	121.93 (19)	C7—C12—S1	118.73 (15)
C1—C2—C3	119.1 (2)	H1W—O4—H2W	110.2
C1—C2—H2	120.5

D—H···A	D—H	H···A	D···A	D—H···A
O4—H1W···O3ii	0.83	2.21	3.014 (3)	162
O4—H2W···O2	0.83	2.06	2.877 (3)	166
C4—H4···O3iii	0.93	2.48	3.407 (3)	175
C6—H6···O4iv	0.93	2.57	3.436 (3)	155

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H1W⋯O3i	0.83	2.21	3.014 (3)	162
O4—H2W⋯O2	0.83	2.06	2.877 (3)	166
C4—H4⋯O3ii	0.93	2.48	3.407 (3)	175
C6—H6⋯O4iii	0.93	2.57	3.436 (3)	155

Symmetry codes: (i) ; (ii) ; (iii) .