catena-Poly[[zinc-μ-[2-(2-{[2-(2-hy-droxy-benzo-yl)hydrazinyl-idene]meth-yl}phen-oxy)acetato-(2-)]] monohydrate].

In the title compound, {[Zn(C(16)H(12)N(2)O(5))]·H(2)O}(n), the unique Zn(II) ion is coordinated in a distorted square-pyramidal environment by three O atoms and one N atom from a symmetry-unique ligand. A symmetry-related ligand provides an O atom from a carboxyl-ate group to complete the coordination in the apical site and generate a one-dimensional polymer parallel to [010]. In addition to an intra-molecular O-H⋯N hydrogen bond, inter-molecular O-H⋯O and weak C-H⋯O hydrogen bonds are observed within the one-dimensional structure.

Related literature

For background information on zinc(II) carboxyl­ate compounds, see: Suen et al. (2002 ▶). For general information on the structures of carboxyl­ate and hydrazone compounds, see: Wu et al. (2007 ▶); Luo et al. (2010 ▶).

Experimental

Crystal data

[Zn(C16H12N2O5)]·H2O

M = 395.66

Monoclinic,

a = 14.730 (2) Å

b = 5.4063 (8) Å

c = 20.983 (3) Å

β = 106.620 (2)°

V = 1601.2 (4) Å3

Z = 4

Mo Kα radiation

μ = 1.57 mm−1

T = 298 K

0.16 × 0.12 × 0.10 mm

Data collection

Bruker SMART CCD diffractometer

9785 measured reflections

3132 independent reflections

2764 reflections with I > 2σ(I)

R int = 0.092

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.109

S = 1.06

3132 reflections

230 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.48 e Å−3

Δρmin = −0.51 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811043510/lh5346sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811043510/lh5346Isup2.hkl

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

[Zn(C16H12N2O5)]·H2O	F(000) = 808
Mr = 395.66	Dx = 1.641 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3978 reflections
a = 14.730 (2) Å	θ = 2.8–27.4°
b = 5.4063 (8) Å	µ = 1.57 mm−1
c = 20.983 (3) Å	T = 298 K
β = 106.620 (2)°	Block, colorless
V = 1601.2 (4) Å3	0.16 × 0.12 × 0.10 mm
Z = 4

Bruker SMART CCD diffractometer	2764 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.092
graphite	θmax = 26.0°, θmin = 2.0°
φ and ω scans	h = −16→18
9785 measured reflections	k = −6→6
3132 independent reflections	l = −25→25

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.109	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0552P)2 + 0.0104P] where P = (Fo2 + 2Fc2)/3
3132 reflections	(Δ/σ)max = 0.001
230 parameters	Δρmax = 0.48 e Å−3
0 restraints	Δρmin = −0.51 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
Zn1	0.37549 (2)	0.04095 (6)	0.273648 (16)	0.03342 (14)
O1	0.33632 (13)	−0.1912 (4)	0.33490 (10)	0.0408 (5)
O2	0.04795 (17)	−0.1639 (6)	0.32481 (16)	0.0713 (8)
O3	0.35695 (13)	0.1914 (4)	0.16947 (9)	0.0381 (5)
O4	0.45124 (12)	−0.1779 (3)	0.23378 (9)	0.0347 (4)
O5	0.54232 (13)	−0.2163 (4)	0.16671 (9)	0.0401 (5)
N1	0.18798 (16)	−0.0372 (4)	0.28074 (13)	0.0380 (6)
N2	0.23483 (15)	0.1069 (4)	0.24511 (11)	0.0320 (5)
C1	0.2011 (2)	−0.3599 (5)	0.35985 (14)	0.0396 (7)
C2	0.1069 (2)	−0.3391 (7)	0.35924 (17)	0.0522 (8)
C3	0.0705 (3)	−0.5039 (8)	0.3972 (2)	0.0722 (12)
H3	0.0084	−0.4860	0.3988	0.087*
C4	0.1252 (3)	−0.6905 (7)	0.43192 (19)	0.0711 (12)
H4	0.0998	−0.8000	0.4564	0.085*
C5	0.2174 (3)	−0.7179 (6)	0.43094 (17)	0.0624 (10)
H5	0.2541	−0.8471	0.4541	0.075*
C6	0.2553 (3)	−0.5528 (5)	0.39543 (16)	0.0475 (8)
H6	0.3181	−0.5705	0.3952	0.057*
C7	0.24582 (19)	−0.1871 (5)	0.32341 (13)	0.0334 (6)
C8	0.1840 (2)	0.2634 (5)	0.20485 (14)	0.0402 (7)
H8	0.1218	0.2832	0.2061	0.048*
C9	0.2143 (2)	0.4136 (5)	0.15722 (14)	0.0364 (6)
C10	0.29665 (18)	0.3766 (5)	0.13731 (13)	0.0317 (6)
C11	0.3143 (2)	0.5182 (5)	0.08720 (15)	0.0384 (7)
H11	0.3689	0.4913	0.0743	0.046*
C12	0.2508 (2)	0.6998 (5)	0.05635 (15)	0.0460 (7)
H12	0.2627	0.7940	0.0225	0.055*
C13	0.1696 (2)	0.7423 (6)	0.07554 (16)	0.0536 (8)
H13	0.1275	0.8663	0.0552	0.064*
C14	0.1519 (2)	0.5995 (6)	0.12493 (17)	0.0516 (8)
H14	0.0969	0.6274	0.1372	0.062*
C15	0.42785 (19)	0.1002 (5)	0.14144 (14)	0.0343 (6)
H15A	0.4731	0.2296	0.1406	0.041*
H15B	0.3992	0.0441	0.0962	0.041*
C16	0.47695 (18)	−0.1127 (5)	0.18446 (13)	0.0332 (6)
O6	0.4589 (3)	0.7641 (10)	0.47903 (19)	0.171 (2)
H60A	0.4249	0.7787	0.4396	0.256*
H60B	0.5164	0.7397	0.4823	0.256*
H20	0.074 (3)	−0.090 (7)	0.305 (2)	0.067 (13)*

	U11	U22	U33	U12	U13	U23
Zn1	0.0246 (2)	0.0419 (2)	0.0363 (2)	0.00089 (12)	0.01278 (15)	0.00451 (13)
O1	0.0301 (10)	0.0488 (12)	0.0463 (12)	0.0011 (9)	0.0154 (9)	0.0140 (9)
O2	0.0348 (13)	0.093 (2)	0.094 (2)	−0.0094 (14)	0.0308 (14)	0.0222 (17)
O3	0.0306 (10)	0.0517 (12)	0.0363 (11)	0.0114 (9)	0.0163 (8)	0.0117 (9)
O4	0.0331 (10)	0.0378 (10)	0.0368 (10)	0.0055 (8)	0.0157 (8)	0.0039 (8)
O5	0.0315 (10)	0.0508 (11)	0.0411 (11)	0.0072 (9)	0.0153 (9)	0.0016 (9)
N1	0.0270 (12)	0.0492 (14)	0.0417 (14)	−0.0039 (10)	0.0160 (11)	0.0052 (11)
N2	0.0240 (11)	0.0389 (12)	0.0354 (13)	0.0020 (9)	0.0123 (10)	0.0045 (10)
C1	0.0453 (17)	0.0440 (16)	0.0323 (15)	−0.0146 (14)	0.0156 (13)	−0.0054 (12)
C2	0.0429 (18)	0.061 (2)	0.055 (2)	−0.0190 (17)	0.0189 (16)	0.0034 (17)
C3	0.067 (3)	0.085 (3)	0.076 (3)	−0.038 (2)	0.038 (2)	−0.004 (2)
C4	0.100 (3)	0.064 (2)	0.058 (2)	−0.043 (2)	0.037 (2)	−0.0004 (19)
C5	0.093 (3)	0.052 (2)	0.0418 (19)	−0.019 (2)	0.0199 (19)	0.0033 (15)
C6	0.059 (2)	0.0452 (17)	0.0401 (18)	−0.0089 (15)	0.0163 (16)	−0.0020 (13)
C7	0.0319 (14)	0.0365 (14)	0.0339 (14)	−0.0066 (11)	0.0130 (12)	−0.0046 (11)
C8	0.0257 (14)	0.0531 (17)	0.0448 (17)	0.0032 (12)	0.0147 (13)	0.0049 (14)
C9	0.0345 (15)	0.0409 (15)	0.0342 (15)	0.0071 (12)	0.0104 (12)	0.0046 (12)
C10	0.0282 (13)	0.0345 (13)	0.0308 (14)	0.0006 (11)	0.0056 (11)	−0.0004 (11)
C11	0.0381 (16)	0.0416 (15)	0.0359 (16)	−0.0031 (12)	0.0112 (13)	0.0004 (12)
C12	0.057 (2)	0.0418 (16)	0.0381 (16)	−0.0013 (14)	0.0127 (15)	0.0060 (13)
C13	0.063 (2)	0.0492 (18)	0.0487 (19)	0.0229 (16)	0.0155 (17)	0.0140 (15)
C14	0.0488 (19)	0.0548 (19)	0.055 (2)	0.0195 (16)	0.0202 (16)	0.0116 (16)
C15	0.0279 (14)	0.0438 (15)	0.0337 (15)	0.0032 (12)	0.0127 (12)	0.0008 (12)
C16	0.0275 (14)	0.0370 (14)	0.0354 (15)	−0.0026 (11)	0.0094 (12)	−0.0041 (12)
O6	0.097 (3)	0.327 (7)	0.087 (3)	−0.054 (4)	0.023 (2)	−0.067 (4)

Zn1—O4	1.9694 (17)	C4—C5	1.372 (6)
Zn1—O5i	1.9717 (19)	C4—H4	0.9300
Zn1—O1	1.9958 (18)	C5—C6	1.379 (4)
Zn1—N2	2.017 (2)	C5—H5	0.9300
Zn1—O3	2.2743 (18)	C6—H6	0.9300
O1—C7	1.285 (3)	C8—C9	1.454 (4)
O2—C2	1.347 (4)	C8—H8	0.9300
O2—H20	0.75 (4)	C9—C14	1.400 (4)
O3—C10	1.380 (3)	C9—C10	1.406 (4)
O3—C15	1.425 (3)	C10—C11	1.385 (4)
O4—C16	1.250 (3)	C11—C12	1.382 (4)
O5—C16	1.259 (3)	C11—H11	0.9300
O5—Zn1ii	1.9717 (19)	C12—C13	1.387 (4)
N1—C7	1.322 (4)	C12—H12	0.9300
N1—N2	1.392 (3)	C13—C14	1.376 (4)
N2—C8	1.276 (3)	C13—H13	0.9300
C1—C2	1.389 (4)	C14—H14	0.9300
C1—C6	1.393 (4)	C15—C16	1.513 (4)
C1—C7	1.476 (4)	C15—H15A	0.9700
C2—C3	1.400 (5)	C15—H15B	0.9700
C3—C4	1.365 (6)	O6—H60A	0.8400
C3—H3	0.9300	O6—H60B	0.8400
O4—Zn1—O5i	110.48 (8)	C5—C6—H6	119.5
O4—Zn1—O1	101.48 (8)	C1—C6—H6	119.5
O5i—Zn1—O1	104.35 (8)	O1—C7—N1	124.8 (2)
O4—Zn1—N2	129.69 (9)	O1—C7—C1	119.0 (2)
O5i—Zn1—N2	117.57 (9)	N1—C7—C1	116.3 (2)
O1—Zn1—N2	80.84 (8)	N2—C8—C9	126.0 (2)
O4—Zn1—O3	74.54 (7)	N2—C8—H8	117.0
O5i—Zn1—O3	104.79 (7)	C9—C8—H8	117.0
O1—Zn1—O3	150.04 (8)	C14—C9—C10	117.5 (3)
N2—Zn1—O3	79.67 (8)	C14—C9—C8	116.5 (3)
C7—O1—Zn1	110.12 (16)	C10—C9—C8	125.9 (2)
C2—O2—H20	109 (3)	O3—C10—C11	122.6 (2)
C10—O3—C15	119.63 (19)	O3—C10—C9	116.6 (2)
C10—O3—Zn1	127.81 (15)	C11—C10—C9	120.9 (3)
C15—O3—Zn1	111.85 (14)	C12—C11—C10	119.9 (3)
C16—O4—Zn1	121.68 (17)	C12—C11—H11	120.0
C16—O5—Zn1ii	119.40 (17)	C10—C11—H11	120.0
C7—N1—N2	112.6 (2)	C11—C12—C13	120.4 (3)
C8—N2—N1	116.1 (2)	C11—C12—H12	119.8
C8—N2—Zn1	132.25 (18)	C13—C12—H12	119.8
N1—N2—Zn1	111.50 (16)	C14—C13—C12	119.4 (3)
C2—C1—C6	118.9 (3)	C14—C13—H13	120.3
C2—C1—C7	122.5 (3)	C12—C13—H13	120.3
C6—C1—C7	118.6 (3)	C13—C14—C9	121.9 (3)
O2—C2—C1	123.4 (3)	C13—C14—H14	119.1
O2—C2—C3	117.4 (3)	C9—C14—H14	119.1
C1—C2—C3	119.2 (4)	O3—C15—C16	107.4 (2)
C4—C3—C2	120.7 (4)	O3—C15—H15A	110.2
C4—C3—H3	119.7	C16—C15—H15A	110.2
C2—C3—H3	119.7	O3—C15—H15B	110.2
C3—C4—C5	120.6 (3)	C16—C15—H15B	110.2
C3—C4—H4	119.7	H15A—C15—H15B	108.5
C5—C4—H4	119.7	O4—C16—O5	123.9 (3)
C4—C5—C6	119.6 (4)	O4—C16—C15	120.1 (2)
C4—C5—H5	120.2	O5—C16—C15	115.9 (2)
C6—C5—H5	120.2	H60A—O6—H60B	113.4
C5—C6—C1	121.0 (3)
O4—Zn1—O1—C7	−126.34 (18)	C7—C1—C6—C5	179.3 (3)
O5i—Zn1—O1—C7	118.79 (18)	Zn1—O1—C7—N1	−4.7 (3)
N2—Zn1—O1—C7	2.52 (18)	Zn1—O1—C7—C1	175.39 (18)
O3—Zn1—O1—C7	−47.4 (3)	N2—N1—C7—O1	4.5 (4)
O4—Zn1—O3—C10	172.7 (2)	N2—N1—C7—C1	−175.7 (2)
O5i—Zn1—O3—C10	−79.7 (2)	C2—C1—C7—O1	168.5 (3)
O1—Zn1—O3—C10	86.5 (2)	C6—C1—C7—O1	−12.4 (4)
N2—Zn1—O3—C10	36.3 (2)	C2—C1—C7—N1	−11.4 (4)
O4—Zn1—O3—C15	−17.10 (17)	C6—C1—C7—N1	167.7 (3)
O5i—Zn1—O3—C15	90.50 (17)	N1—N2—C8—C9	−172.7 (3)
O1—Zn1—O3—C15	−103.3 (2)	Zn1—N2—C8—C9	12.9 (5)
N2—Zn1—O3—C15	−153.49 (18)	N2—C8—C9—C14	−170.7 (3)
O5i—Zn1—O4—C16	−81.2 (2)	N2—C8—C9—C10	14.4 (5)
O1—Zn1—O4—C16	168.6 (2)	C15—O3—C10—C11	−15.1 (4)
N2—Zn1—O4—C16	81.0 (2)	Zn1—O3—C10—C11	154.5 (2)
O3—Zn1—O4—C16	19.1 (2)	C15—O3—C10—C9	164.0 (2)
C7—N1—N2—C8	−177.3 (2)	Zn1—O3—C10—C9	−26.5 (3)
C7—N1—N2—Zn1	−1.6 (3)	C14—C9—C10—O3	−179.6 (3)
O4—Zn1—N2—C8	−88.4 (3)	C8—C9—C10—O3	−4.7 (4)
O5i—Zn1—N2—C8	72.7 (3)	C14—C9—C10—C11	−0.5 (4)
O1—Zn1—N2—C8	174.2 (3)	C8—C9—C10—C11	174.3 (3)
O3—Zn1—N2—C8	−28.7 (3)	O3—C10—C11—C12	179.4 (2)
O4—Zn1—N2—N1	96.90 (19)	C9—C10—C11—C12	0.4 (4)
O5i—Zn1—N2—N1	−101.94 (17)	C10—C11—C12—C13	0.4 (4)
O1—Zn1—N2—N1	−0.47 (17)	C11—C12—C13—C14	−1.0 (5)
O3—Zn1—N2—N1	156.67 (18)	C12—C13—C14—C9	0.8 (5)
C6—C1—C2—O2	−178.0 (3)	C10—C9—C14—C13	−0.1 (5)
C7—C1—C2—O2	1.2 (5)	C8—C9—C14—C13	−175.4 (3)
C6—C1—C2—C3	3.5 (5)	C10—O3—C15—C16	−175.6 (2)
C7—C1—C2—C3	−177.4 (3)	Zn1—O3—C15—C16	13.3 (2)
O2—C2—C3—C4	178.1 (4)	Zn1—O4—C16—O5	162.7 (2)
C1—C2—C3—C4	−3.2 (6)	Zn1—O4—C16—C15	−18.2 (3)
C2—C3—C4—C5	0.9 (6)	Zn1ii—O5—C16—O4	−10.5 (4)
C3—C4—C5—C6	1.1 (6)	Zn1ii—O5—C16—C15	170.31 (18)
C4—C5—C6—C1	−0.7 (5)	O3—C15—C16—O4	0.8 (3)
C2—C1—C6—C5	−1.5 (5)	O3—C15—C16—O5	180.0 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H20···N1	0.75 (4)	1.92 (4)	2.583 (3)	148 (4)
O6—H60A···O1iii	0.84	2.22	3.056 (4)	179.
C8—H8···O2iv	0.93	2.41	3.316 (4)	164.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H20⋯N1	0.75 (4)	1.92 (4)	2.583 (3)	148 (4)
O6—H60A⋯O1i	0.84	2.22	3.056 (4)	179
C8—H8⋯O2ii	0.93	2.41	3.316 (4)	164

Symmetry codes: (i) ; (ii) .