catena-Poly[[zinc-μ-[2-(2-{[2-(2-hy­droxy­benzo­yl)hydrazinyl­idene]meth­yl}phen­oxy)acetato­(2–)]] monohydrate]

Luo, F.; Yang, L.; Zhang, P.; Liu, D.

doi:10.1107/S1600536811043510

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 11| November 2011| Page m1608

doi:10.1107/S1600536811043510

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catena-Poly[[zinc-μ-[2-(2-{[2-(2-hydroxybenzoyl)hydrazinylidene]methyl}phenoxy)acetato(2–)]] monohydrate]

Feihua Luo,^a ^* Li Yang,^a Ping Zhang ^a and Dan Liu ^a

^aDepartment of Chemistry and Chemical Engineering, Sichuan University of Arts and Science, Dazhou, Sichuan 635000, People's Republic of China
^*Correspondence e-mail: luofh2005@yahoo.com.cn

(Received 28 September 2011; accepted 20 October 2011; online 29 October 2011)

In the title compound, {[Zn(C₁₆H₁₂N₂O₅)]·H₂O}_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 carboxylate group to complete the coordination in the apical site and generate a one-dimensional polymer parallel to [010]. In addition to an intramolecular O—H⋯N hydrogen bond, intermolecular 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_r = 395.66
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.042
wR(F²) = 0.109
S = 1.06
3132 reflections
230 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.48 e Å⁻³
Δρ_min = −0.51 e Å⁻³

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) x, y+1, z; (ii) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811043510/lh5346sup1.cif

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

checkCIF report

Comment top

Zn(II) carboxylates, especially those with nitrogen donor ligands, have been the subject of numerous investigations (Suen et al., 2002). Different coordination modes of carboxylate groups can form mononuclear and polynuclear structures. Hydrazone with carboxylate groups can also form mononuclear and polynuclear structures in different conditions (Wu et al., 2007; Luo et al., 2010). Herein we report the synthesis and crystal structure of the title compound.

Part of the one-dimensional structure is shown in Fig. 1. 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 carboxylate group to complete the coordination in the apical site and generate a one-dimensional polymer parallel to [010] (Fig 2). In addition to an intramolecular O—H···N hydrogen bond, intermolecular O—H···O and weak C—H···O hydrogen bonds are observed within the one

Related literature top

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 top

The hydrazone ligand was synthesized according to the literature procedure (Luo et al., 2010). Zinc(II) acetate monohydrate (1 mmol) was dissolved in methanol (15 ml), to which a solution of the ligand (2.5 mmol) in dimethylformamide (15 ml) was added. The mixture was stirred for 3 h at room temperature. An light-yellow solution was obtained, the solution was filtered and allowed to stand at room temperature for three weeks, where upon colorless block-shaped crystals were obtained.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); 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).

Figures top

	Fig. 1. The molecular structure of with displacement ellipsoids drawn at the 30% probability level [symmetry codes: (a) -x+1, y-1/2, -z+1/2; (b) -x+1, y+1/2, -z+1/2]. H atoms are not shown.
	Fig. 2. Part of the crystal structure with hydrogen bonds drawn as dashed lines. Only H atoms involved in hydrogen bonds are shown.

catena-Poly[[zinc-µ-[2-(2-{[2-(2- hydroxybenzoyl)hydrazinylidene]methyl}phenoxy)acetato(2-)]] monohydrate] top

Crystal data top

[Zn(C₁₆H₁₂N₂O₅)]·H₂O	F(000) = 808
M_r = 395.66	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0552P)² + 0.0104P] where P = (F_o² + 2F_c²)/3
3132 reflections	(Δ/σ)_max = 0.001
230 parameters	Δρ_max = 0.48 e Å⁻³
0 restraints	Δρ_min = −0.51 e Å⁻³

Crystal data top

[Zn(C₁₆H₁₂N₂O₅)]·H₂O	V = 1601.2 (4) Å³
M_r = 395.66	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 14.730 (2) Å	µ = 1.57 mm⁻¹
b = 5.4063 (8) Å	T = 298 K
c = 20.983 (3) Å	0.16 × 0.12 × 0.10 mm
β = 106.620 (2)°

Data collection top

Bruker SMART CCD diffractometer	2764 reflections with I > 2σ(I)
9785 measured reflections	R_int = 0.092
3132 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.109	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.48 e Å⁻³
3132 reflections	Δρ_min = −0.51 e Å⁻³
230 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) −x+1, y−1/2, −z+1/2.

Hydrogen-bond geometry (Å, º) top

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···O2^iv	0.93	2.41	3.316 (4)	164

Symmetry codes: (iii) x, y+1, z; (iv) −x, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	[Zn(C₁₆H₁₂N₂O₅)]·H₂O
M_r	395.66
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	14.730 (2), 5.4063 (8), 20.983 (3)
β (°)	106.620 (2)
V (Å³)	1601.2 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.57
Crystal size (mm)	0.16 × 0.12 × 0.10

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	9785, 3132, 2764
R_int	0.092
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.109, 1.06
No. of reflections	3132
No. of parameters	230
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.48, −0.51

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

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)	178.7
C8—H8···O2ⁱⁱ	0.93	2.41	3.316 (4)	163.5

Symmetry codes: (i) x, y+1, z; (ii) −x, y+1/2, −z+1/2.

References

Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Luo, F. H., Hu, Z. Q. & Yang, L. (2010). Chin. J. Inorg. Chem. 26, 682–686. CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Suen, M. C., Keng, T. C. & Wang, J. C. (2002). Polyhedron, 21, 2705–2710. Web of Science CSD CrossRef CAS Google Scholar
Wu, L. M., Qiu, G. F. & Teng, H. B. (2007). Inorg. Chim. Acta, 360, 3069–3074. Web of Science CSD CrossRef CAS Google Scholar

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Volume 67| Part 11| November 2011| Page m1608

doi:10.1107/S1600536811043510

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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

catena-Poly[[zinc-μ-[2-(2-{[2-(2-hy­dr­oxy­benzo­yl)hydrazinyl­­idene]meth­yl}phen­­oxy)acetato­(2–)]] monohydrate]

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

References

metal-organic compounds

catena-Poly[[zinc-μ-[2-(2-{[2-(2-hydroxybenzoyl)hydrazinylidene]methyl}phenoxy)acetato(2–)]] monohydrate]