Diaqua-bis-{2-hy-droxy-5-[(pyridin-2-yl)methyl-idene-amino]-benzoato-κN,N'}zinc(II) dihydrate.

The complex mol-ecule of the title compound, [Zn(C(13)H(9)N(2)O(3))(2)(H(2)O)(2)]·2H(2)O, has 2 symmetry with the Zn(II) cation located on a twofold rotation axis. The Zn cation is N,N'-chelated by two 5-[(pyridin-2-yl)methyl-idene-amino]-2-hy-droxy-benzoate anions and coordinated by two water mol-ecules in a distorted octa-hedral geometry. Within the anionic ligand, the pyridine ring is oriented at a dihedral angle of 49.54 (10)° with respect to the benzene ring. The carboxyl-ate group of the anionic ligand is not involved in coordination but is O-H⋯O hydrogen bonded to the coordinated and uncoordinated water mol-ecules. Weak inter-molecular C-H⋯O hydrogen bonding is also present in the crystal structure.

Related literature

The title compound is a Schiff base complex; for potential applications of Schiff base compounds, see: Bourque et al. (2005 ▶); Donald & Osit (2010 ▶); Feng et al. (2007 ▶); Gang et al. (2007 ▶); Shanta et al. (2003 ▶).

Experimental

Crystal data

[Zn(C13H9N2O3)2(H2O)2]·2H2O

M = 619.90

Orthorhombic,

a = 15.812 (2) Å

b = 10.6962 (15) Å

c = 15.636 (2) Å

V = 2644.5 (6) Å3

Z = 4

Mo Kα radiation

μ = 1.00 mm−1

T = 296 K

0.43 × 0.32 × 0.27 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.689, T max = 0.764

21797 measured reflections

3041 independent reflections

2291 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.083

S = 1.03

3041 reflections

206 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.33 e Å−3

Δρmin = −0.29 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681004496X/xu5074sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681004496X/xu5074Isup2.hkl

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

[Zn(C13H9N2O3)2(H2O)2]·2H2O	F(000) = 1280
Mr = 619.90	Dx = 1.557 Mg m−3
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 5445 reflections
a = 15.812 (2) Å	θ = 2.3–26.5°
b = 10.6962 (15) Å	µ = 1.00 mm−1
c = 15.636 (2) Å	T = 296 K
V = 2644.5 (6) Å3	Block, yellow
Z = 4	0.43 × 0.32 × 0.27 mm

Bruker SMART APEX CCD area-detector diffractometer	3041 independent reflections
Radiation source: fine-focus sealed tube	2291 reflections with I > 2σ(I)
graphite	Rint = 0.038
φ and ω scans	θmax = 27.5°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −20→20
Tmin = 0.689, Tmax = 0.764	k = −13→13
21797 measured reflections	l = −20→20

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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.083	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0389P)2 + 0.7619P] where P = (Fo2 + 2Fc2)/3
3041 reflections	(Δ/σ)max < 0.001
206 parameters	Δρmax = 0.33 e Å−3
0 restraints	Δρmin = −0.29 e Å−3

Experimental. IR (KBr, cm-1): 3455(versus), 3088(w), 2924(w), 2361(w), 1919(w), 1668(s), 1602(m), 1578(m), 1489(versus), 1447(m), 1364(versus), 1299(m), 1245(s), 1161(m), 1084(m), 1054(s), 959(w), 893(m), 839(s), 792(versus), 655(m), 572(m), 512(m).

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	0.5000	0.40959 (2)	0.2500	0.03779 (10)
O1	0.49550 (12)	0.53276 (14)	0.14990 (11)	0.0590 (4)
O2	0.70387 (10)	−0.06373 (16)	−0.00402 (11)	0.0623 (4)
O3	0.62843 (10)	−0.24718 (13)	0.05467 (11)	0.0670 (4)
O4	0.51579 (10)	−0.22474 (13)	0.13984 (11)	0.0615 (4)
O5	0.37521 (14)	0.47962 (17)	0.02876 (13)	0.0709 (5)
N1	0.36496 (10)	0.39448 (14)	0.24957 (9)	0.0414 (4)
N2	0.47286 (10)	0.24704 (13)	0.16032 (9)	0.0364 (3)
C1	0.31145 (14)	0.4780 (2)	0.28233 (14)	0.0525 (5)
H1A	0.3329	0.5440	0.3144	0.063*
C2	0.22455 (15)	0.4697 (2)	0.27010 (15)	0.0625 (6)
H2A	0.1889	0.5311	0.2919	0.075*
C3	0.19182 (15)	0.3703 (2)	0.22564 (16)	0.0643 (6)
H3A	0.1337	0.3615	0.2190	0.077*
C4	0.24669 (13)	0.2838 (2)	0.19101 (14)	0.0537 (5)
H4A	0.2262	0.2158	0.1603	0.064*
C5	0.33299 (12)	0.30015 (17)	0.20284 (12)	0.0416 (4)
C6	0.39452 (12)	0.21815 (16)	0.16127 (12)	0.0415 (4)
H6A	0.3765	0.1445	0.1354	0.050*
C7	0.53077 (12)	0.16496 (16)	0.11906 (11)	0.0363 (4)
C8	0.59723 (12)	0.21657 (17)	0.07233 (12)	0.0458 (4)
H8A	0.6034	0.3029	0.0695	0.055*
C9	0.65391 (13)	0.14022 (19)	0.03025 (13)	0.0507 (5)
H9A	0.6977	0.1753	−0.0014	0.061*
C10	0.64583 (12)	0.01035 (18)	0.03502 (13)	0.0444 (4)
C11	0.57989 (11)	−0.04244 (16)	0.08294 (12)	0.0386 (4)
C12	0.52303 (11)	0.03585 (16)	0.12417 (11)	0.0374 (4)
H12A	0.4790	0.0013	0.1558	0.045*
C13	0.57306 (13)	−0.18215 (17)	0.09375 (13)	0.0470 (5)
H1	0.5058 (16)	0.606 (3)	0.152 (2)	0.081 (10)*
H2	0.4595 (18)	0.517 (3)	0.1115 (18)	0.083 (9)*
H3	0.3812 (19)	0.417 (3)	−0.005 (2)	0.084 (9)*
H4	0.326 (2)	0.507 (3)	0.025 (2)	0.124 (14)*
H5	0.685 (2)	−0.146 (3)	0.009 (2)	0.117 (11)*

	U11	U22	U33	U12	U13	U23
Zn1	0.04294 (17)	0.02329 (15)	0.04715 (18)	0.000	−0.00043 (13)	0.000
O1	0.0828 (11)	0.0317 (8)	0.0625 (9)	−0.0157 (8)	−0.0203 (9)	0.0127 (7)
O2	0.0562 (9)	0.0523 (9)	0.0785 (11)	−0.0026 (7)	0.0186 (8)	−0.0231 (8)
O3	0.0642 (9)	0.0356 (8)	0.1011 (12)	0.0057 (7)	0.0064 (9)	−0.0178 (8)
O4	0.0744 (11)	0.0280 (7)	0.0820 (11)	−0.0052 (7)	0.0102 (8)	0.0028 (7)
O5	0.0746 (12)	0.0529 (10)	0.0851 (12)	0.0051 (9)	−0.0225 (10)	−0.0171 (9)
N1	0.0442 (8)	0.0357 (8)	0.0443 (8)	0.0064 (6)	0.0028 (7)	0.0041 (7)
N2	0.0446 (8)	0.0241 (7)	0.0406 (8)	0.0009 (6)	0.0000 (6)	0.0006 (6)
C1	0.0608 (13)	0.0453 (12)	0.0514 (11)	0.0133 (10)	0.0115 (10)	0.0046 (9)
C2	0.0562 (13)	0.0630 (15)	0.0684 (15)	0.0221 (11)	0.0210 (11)	0.0172 (12)
C3	0.0452 (12)	0.0712 (16)	0.0764 (15)	0.0103 (11)	0.0067 (11)	0.0232 (13)
C4	0.0462 (11)	0.0533 (12)	0.0616 (13)	−0.0023 (9)	−0.0050 (10)	0.0108 (10)
C5	0.0427 (10)	0.0356 (9)	0.0466 (10)	0.0005 (8)	−0.0012 (8)	0.0081 (8)
C6	0.0466 (11)	0.0302 (9)	0.0477 (10)	−0.0031 (8)	−0.0059 (8)	−0.0008 (8)
C7	0.0402 (9)	0.0283 (9)	0.0404 (9)	−0.0013 (7)	−0.0009 (8)	−0.0014 (7)
C8	0.0593 (12)	0.0284 (9)	0.0497 (10)	−0.0078 (8)	0.0067 (9)	−0.0001 (8)
C9	0.0572 (12)	0.0423 (11)	0.0525 (11)	−0.0125 (9)	0.0166 (10)	−0.0025 (9)
C10	0.0457 (10)	0.0416 (10)	0.0459 (10)	−0.0015 (8)	0.0015 (9)	−0.0118 (8)
C11	0.0429 (10)	0.0285 (8)	0.0443 (10)	−0.0031 (7)	−0.0054 (8)	−0.0039 (7)
C12	0.0394 (9)	0.0290 (9)	0.0438 (10)	−0.0047 (7)	−0.0017 (7)	0.0000 (7)
C13	0.0533 (12)	0.0284 (9)	0.0593 (12)	0.0014 (8)	−0.0092 (10)	−0.0067 (9)

Zn1—O1i	2.0471 (15)	C1—H1A	0.9300
Zn1—O1	2.0471 (15)	C2—C3	1.372 (4)
Zn1—N1i	2.1414 (17)	C2—H2A	0.9300
Zn1—N1	2.1414 (17)	C3—C4	1.379 (3)
Zn1—N2	2.2746 (14)	C3—H3A	0.9300
Zn1—N2i	2.2746 (14)	C4—C5	1.388 (3)
O1—H1	0.81 (3)	C4—H4A	0.9300
O1—H2	0.84 (3)	C5—C6	1.462 (3)
O2—C10	1.357 (2)	C6—H6A	0.9300
O2—H5	0.95 (3)	C7—C12	1.389 (2)
O3—C13	1.274 (2)	C7—C8	1.394 (3)
O4—C13	1.244 (2)	C8—C9	1.380 (3)
O5—H3	0.86 (3)	C8—H8A	0.9300
O5—H4	0.84 (4)	C9—C10	1.397 (3)
N1—C1	1.333 (2)	C9—H9A	0.9300
N1—C5	1.344 (2)	C10—C11	1.403 (3)
N2—C6	1.277 (2)	C11—C12	1.388 (2)
N2—C7	1.423 (2)	C11—C13	1.508 (2)
C1—C2	1.390 (3)	C12—H12A	0.9300
O1i—Zn1—O1	99.88 (10)	C2—C3—H3A	120.6
O1i—Zn1—N1i	90.66 (6)	C4—C3—H3A	120.6
O1—Zn1—N1i	94.92 (7)	C3—C4—C5	118.8 (2)
O1i—Zn1—N1	94.92 (7)	C3—C4—H4A	120.6
O1—Zn1—N1	90.66 (6)	C5—C4—H4A	120.6
N1i—Zn1—N1	171.34 (8)	N1—C5—C4	122.45 (18)
O1i—Zn1—N2	165.91 (6)	N1—C5—C6	116.20 (16)
O1—Zn1—N2	90.80 (6)	C4—C5—C6	121.29 (18)
N1i—Zn1—N2	97.61 (5)	N2—C6—C5	120.37 (16)
N1—Zn1—N2	75.65 (6)	N2—C6—H6A	119.8
O1i—Zn1—N2i	90.80 (6)	C5—C6—H6A	119.8
O1—Zn1—N2i	165.91 (6)	C12—C7—C8	119.37 (17)
N1i—Zn1—N2i	75.65 (6)	C12—C7—N2	122.05 (16)
N1—Zn1—N2i	97.61 (5)	C8—C7—N2	118.58 (15)
N2—Zn1—N2i	80.29 (7)	C9—C8—C7	120.36 (17)
Zn1—O1—H1	126 (2)	C9—C8—H8A	119.8
Zn1—O1—H2	115.9 (19)	C7—C8—H8A	119.8
H1—O1—H2	111 (3)	C8—C9—C10	120.25 (17)
C10—O2—H5	103 (2)	C8—C9—H9A	119.9
H3—O5—H4	109 (3)	C10—C9—H9A	119.9
C1—N1—C5	118.25 (18)	O2—C10—C9	119.64 (18)
C1—N1—Zn1	125.53 (15)	O2—C10—C11	120.52 (18)
C5—N1—Zn1	115.68 (12)	C9—C10—C11	119.79 (17)
C6—N2—C7	118.70 (15)	C12—C11—C10	119.14 (16)
C6—N2—Zn1	111.15 (12)	C12—C11—C13	119.98 (17)
C7—N2—Zn1	129.02 (12)	C10—C11—C13	120.80 (17)
N1—C1—C2	122.1 (2)	C11—C12—C7	121.09 (17)
N1—C1—H1A	118.9	C11—C12—H12A	119.5
C2—C1—H1A	118.9	C7—C12—H12A	119.5
C3—C2—C1	119.5 (2)	O4—C13—O3	125.32 (18)
C3—C2—H2A	120.3	O4—C13—C11	118.69 (17)
C1—C2—H2A	120.3	O3—C13—C11	115.98 (18)
C2—C3—C4	118.8 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O4ii	0.80 (3)	1.83 (3)	2.618 (2)	169 (3)
O1—H2···O5	0.84 (3)	1.90 (3)	2.744 (3)	178 (3)
O5—H3···O3iii	0.86 (3)	1.98 (3)	2.808 (2)	161 (3)
O5—H4···O2iv	0.83 (3)	2.05 (3)	2.881 (3)	174 (3)
O2—H5···O3	0.95 (3)	1.58 (3)	2.473 (2)	156 (3)
C6—H6A···O2iii	0.93	2.57	3.346 (3)	142

Table 1

Selected bond lengths (Å)

Zn1—O1	2.0471 (15)
Zn1—N1	2.1414 (17)
Zn1—N2	2.2746 (14)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O4i	0.80 (3)	1.83 (3)	2.618 (2)	169 (3)
O1—H2⋯O5	0.84 (3)	1.90 (3)	2.744 (3)	178 (3)
O5—H3⋯O3ii	0.86 (3)	1.98 (3)	2.808 (2)	161 (3)
O5—H4⋯O2iii	0.83 (3)	2.05 (3)	2.881 (3)	174 (3)
O2—H5⋯O3	0.95 (3)	1.58 (3)	2.473 (2)	156 (3)
C6—H6A⋯O2ii	0.93	2.57	3.346 (3)	142

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