Tetra-aqua-bis-[2-(2-oxo-2,3-dihydro-1,3-benzoxazol-3-yl)acetato]-zinc.

The Zn(II) ion in the title compound, [Zn(C(9)H(6)NO(4))(2)(H(2)O)(4)], is located on an inversion center and is octa-hedrally coordinated by two 2-(2-oxo-2,3-dihydro-1,3-benzoxazol-3-yl)acetate anions in axial sites and four water mol-ecules in equatorial positions. In the crystal, O-H⋯O hydrogen bonds between the coordinated water mol-ecules and carbon-yl-carboxyl-ate O atoms lead to pleated sheets parallel to (001).

Related literature

For the synthesis of 3-alkanoic acid derivatives of 2(3H)-benzoxazolone, see: Lespagnol et al. (1967 ▶). For the biological activity of 2(3H)-benzoxazolone derivatives, see: Önkol et al. (2004 ▶). For the structure of a 2(3H)-benzoxazolone metal complex, see: Wagler & Hill (2008 ▶).

Experimental

Crystal data

[Zn(C9H6NO4)2(H2O)4]

M = 521.73

Monoclinic,

a = 6.144 (3) Å

b = 5.342 (1) Å

c = 30.595 (2) Å

β = 94.80 (5)°

V = 1000.6 (6) Å3

Z = 2

Cu Kα radiation

μ = 2.38 mm−1

T = 293 K

0.50 × 0.35 × 0.20 mm

Data collection

Oxford Diffraction Xcalibur Ruby diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T min = 0.726, T max = 1.000

5344 measured reflections

1745 independent reflections

1168 reflections with I > 2σ(I)

R int = 0.065

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.150

S = 1.06

1745 reflections

151 parameters

H-atom parameters constrained

Δρmax = 0.80 e Å−3

Δρmin = −0.34 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP (Bruker, 1998 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811007999/mw2002sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811007999/mw2002Isup2.hkl

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

[Zn(C9H6NO4)2(H2O)4]	F(000) = 536
Mr = 521.73	Dx = 1.732 Mg m−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.54180 Å
Hall symbol: -P 2yn	Cell parameters from 4608 reflections
a = 6.144 (3) Å	θ = 7.6–66.2°
b = 5.342 (1) Å	µ = 2.38 mm−1
c = 30.595 (2) Å	T = 293 K
β = 94.80 (5)°	Prism, colourless
V = 1000.6 (6) Å3	0.50 × 0.35 × 0.20 mm
Z = 2

Oxford Diffraction Xcalibur Ruby diffractometer	1745 independent reflections
Radiation source: Enhance (Cu) X-ray Source	1168 reflections with I > 2σ(I)
graphite	Rint = 0.065
Detector resolution: 10.2576 pixels mm-1	θmax = 66.7°, θmin = 5.8°
ω scans	h = −7→6
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −3→6
Tmin = 0.726, Tmax = 1.000	l = −35→36
5344 measured reflections

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.150	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0732P)2 + 0.5645P] where P = (Fo2 + 2Fc2)/3
1745 reflections	(Δ/σ)max < 0.001
151 parameters	Δρmax = 0.80 e Å−3
0 restraints	Δρmin = −0.34 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 > 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. H-atoms attached to carbon were placed in calculated positions (C—H = 0.95 - 0.98 Å) while those attached to oxygen were placed in locations derived from a difference map and their positions adjusted to provide reasonable geometries for the coordinated water molecules. All were included as riding contributions with isotropic displacement parameters 1.2 - 1.5 times those of the attached atoms.

	x	y	z	Uiso*/Ueq
Zn1	1.0000	0.0000	0.0000	0.0416 (3)
O1	0.2330 (6)	0.1894 (7)	0.17363 (12)	0.0481 (9)
O2	0.1804 (6)	0.4884 (7)	0.12215 (13)	0.0578 (10)
O3	0.5737 (6)	−0.0487 (6)	0.05893 (11)	0.0432 (9)
O4	0.7938 (6)	0.2347 (6)	0.03233 (11)	0.0446 (9)
N1	0.4944 (7)	0.2399 (8)	0.12870 (14)	0.0427 (10)
C1	0.2944 (9)	0.3231 (10)	0.13871 (17)	0.0448 (13)
C2	0.5608 (8)	0.0474 (9)	0.15703 (16)	0.0386 (12)
C3	0.7425 (9)	−0.1051 (10)	0.16032 (18)	0.0469 (14)
H3A	0.8541	−0.0866	0.1418	0.056*
C4	0.7500 (10)	−0.2885 (11)	0.19291 (19)	0.0563 (15)
H4A	0.8694	−0.3959	0.1962	0.068*
C5	0.5830 (10)	−0.3139 (11)	0.22046 (19)	0.0599 (16)
H5A	0.5939	−0.4364	0.2421	0.072*
C6	0.4014 (10)	−0.1616 (11)	0.21642 (18)	0.0547 (15)
H6A	0.2885	−0.1791	0.2346	0.066*
C7	0.3957 (8)	0.0144 (10)	0.18462 (16)	0.0438 (12)
C8	0.6179 (9)	0.3428 (10)	0.09484 (17)	0.0479 (14)
H8A	0.7561	0.4046	0.1083	0.057*
H8B	0.5385	0.4845	0.0816	0.057*
C9	0.6627 (8)	0.1603 (10)	0.05923 (16)	0.0397 (12)
O1W	1.1399 (6)	−0.1149 (7)	0.06222 (12)	0.0539 (10)
H1A	1.1269	−0.2588	0.0711	0.065*
H1B	1.2722	−0.0835	0.0699	0.065*
O2W	1.2325 (5)	0.2871 (6)	0.00289 (11)	0.0469 (9)
H2A	1.3514	0.2751	−0.0076	0.056*
H2B	1.2014	0.4359	−0.0014	0.056*

	U11	U22	U33	U12	U13	U23
Zn1	0.0426 (6)	0.0316 (5)	0.0524 (6)	0.0037 (5)	0.0147 (4)	0.0050 (5)
O1	0.046 (2)	0.045 (2)	0.056 (2)	0.0049 (18)	0.0188 (17)	0.0053 (18)
O2	0.059 (2)	0.050 (2)	0.067 (3)	0.016 (2)	0.0170 (19)	0.014 (2)
O3	0.045 (2)	0.036 (2)	0.050 (2)	−0.0054 (16)	0.0131 (16)	0.0012 (16)
O4	0.052 (2)	0.032 (2)	0.053 (2)	0.0059 (16)	0.0225 (17)	0.0060 (17)
N1	0.049 (3)	0.038 (3)	0.043 (2)	0.000 (2)	0.0105 (19)	0.001 (2)
C1	0.043 (3)	0.044 (3)	0.048 (3)	0.002 (3)	0.009 (2)	−0.003 (3)
C2	0.045 (3)	0.032 (3)	0.039 (3)	−0.002 (2)	0.006 (2)	−0.002 (2)
C3	0.042 (3)	0.044 (3)	0.055 (4)	0.001 (2)	0.003 (2)	−0.004 (3)
C4	0.058 (4)	0.047 (4)	0.062 (4)	0.006 (3)	−0.010 (3)	−0.006 (3)
C5	0.080 (5)	0.044 (4)	0.054 (4)	0.001 (3)	−0.006 (3)	0.006 (3)
C6	0.065 (4)	0.050 (4)	0.050 (4)	−0.009 (3)	0.009 (3)	0.010 (3)
C7	0.051 (3)	0.040 (3)	0.041 (3)	0.004 (3)	0.009 (2)	−0.004 (3)
C8	0.050 (3)	0.041 (3)	0.054 (3)	−0.006 (3)	0.016 (3)	0.006 (3)
C9	0.040 (3)	0.043 (3)	0.037 (3)	0.009 (2)	0.006 (2)	0.007 (2)
O1W	0.041 (2)	0.055 (2)	0.066 (3)	0.0016 (18)	0.0051 (18)	0.016 (2)
O2W	0.048 (2)	0.0305 (19)	0.064 (2)	0.0012 (16)	0.0170 (17)	0.0037 (17)

Zn1—O4i	2.089 (3)	C3—C4	1.396 (8)
Zn1—O4	2.089 (3)	C3—H3A	0.9300
Zn1—O2W	2.093 (3)	C4—C5	1.388 (8)
Zn1—O2Wi	2.093 (3)	C4—H4A	0.9300
Zn1—O1W	2.113 (4)	C5—C6	1.378 (8)
Zn1—O1Wi	2.113 (4)	C5—H5A	0.9300
O1—C1	1.364 (6)	C6—C7	1.351 (8)
O1—C7	1.389 (6)	C6—H6A	0.9300
O2—C1	1.212 (6)	C8—C9	1.504 (7)
O3—C9	1.243 (6)	C8—H8A	0.9700
O4—C9	1.263 (6)	C8—H8B	0.9700
N1—C1	1.365 (6)	O1W—H1A	0.8218
N1—C2	1.384 (6)	O1W—H1B	0.8439
N1—C8	1.443 (6)	O2W—H2A	0.8249
C2—C3	1.379 (7)	O2W—H2B	0.8256
C2—C7	1.384 (7)
O4i—Zn1—O4	180.00 (15)	C4—C3—H3A	121.8
O4i—Zn1—O2W	91.20 (13)	C5—C4—C3	121.4 (6)
O4—Zn1—O2W	88.81 (13)	C5—C4—H4A	119.3
O4i—Zn1—O2Wi	88.80 (13)	C3—C4—H4A	119.3
O4—Zn1—O2Wi	91.20 (13)	C6—C5—C4	121.5 (6)
O2W—Zn1—O2Wi	180.0	C6—C5—H5A	119.3
O4i—Zn1—O1W	92.02 (14)	C4—C5—H5A	119.3
O4—Zn1—O1W	87.98 (14)	C7—C6—C5	116.6 (6)
O2W—Zn1—O1W	87.14 (14)	C7—C6—H6A	121.7
O2Wi—Zn1—O1W	92.86 (14)	C5—C6—H6A	121.7
O4i—Zn1—O1Wi	87.98 (14)	C6—C7—C2	123.5 (5)
O4—Zn1—O1Wi	92.02 (14)	C6—C7—O1	128.1 (5)
O2W—Zn1—O1Wi	92.86 (14)	C2—C7—O1	108.4 (4)
O2Wi—Zn1—O1Wi	87.14 (14)	N1—C8—C9	114.4 (4)
O1W—Zn1—O1Wi	180.0	N1—C8—H8A	108.7
C1—O1—C7	107.6 (4)	C9—C8—H8A	108.7
C9—O4—Zn1	124.4 (3)	N1—C8—H8B	108.7
C1—N1—C2	109.0 (4)	C9—C8—H8B	108.7
C1—N1—C8	125.0 (4)	H8A—C8—H8B	107.6
C2—N1—C8	126.0 (4)	O3—C9—O4	125.6 (5)
O2—C1—O1	121.4 (5)	O3—C9—C8	118.7 (4)
O2—C1—N1	130.0 (5)	O4—C9—C8	115.7 (5)
O1—C1—N1	108.5 (4)	Zn1—O1W—H1A	121.8
C3—C2—N1	132.8 (5)	Zn1—O1W—H1B	120.1
C3—C2—C7	120.7 (5)	H1A—O1W—H1B	102.2
N1—C2—C7	106.5 (4)	Zn1—O2W—H2A	123.4
C2—C3—C4	116.4 (5)	Zn1—O2W—H2B	123.4
C2—C3—H3A	121.8	H2A—O2W—H2B	102.3

D—H···A	D—H	H···A	D···A	D—H···A
O2W—H2B···O4ii	0.83	2.00	2.772 (5)	156
O1W—H1B···O3iii	0.84	1.92	2.699 (5)	153
O1W—H1A···O2iv	0.82	2.07	2.799 (5)	148

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2W—H2B⋯O4i	0.83	2.00	2.772 (5)	156
O1W—H1B⋯O3ii	0.84	1.92	2.699 (5)	153
O1W—H1A⋯O2iii	0.82	2.07	2.799 (5)	148

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