Penta­aqua­[2-(5-carboxyl­ato-2-oxido-1-pyridinio)acetato]zinc(II) monohydrate

Chen, J.; Feng, Y.-L.

doi:10.1107/S1600536810017538

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 7| July 2010| Page m759

doi:10.1107/S1600536810017538

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Pentaaqua[2-(5-carboxylato-2-oxido-1-pyridinio)acetato]zinc(II) monohydrate

Jing Chen ^a and Yun-Long Feng ^a ^*

^aZhejiang Key Laboratory for Reactive Chemistry on Solid Surfaces, Institute of Physical Chemistry, Zhejiang Normal University, Jinhua, Zhejiang 321004, People's Republic of China
^*Correspondence e-mail: sky37@zjnu.cn

(Received 20 April 2010; accepted 12 May 2010; online 9 June 2010)

In the title compound, [Zn(C₈H₅NO₅)(H₂O)₅]·H₂O, the Zn^II atom is coordinated by one O atom from the 2-(5-carboxylato-2-oxidopyridinium-1-yl)acetate ligand and by five water molecules, forming a distorted octahedral geometry. Coordinated and uncoordinated water molecules form O—H⋯O hydrogen bonds, leading to a three-dimensional framework.

Related literature

For related structures, see: Jiang et al. (2009 ); Szafran et al. (2006 ); Yang et al. (2010 ); Zhang et al. (2003 ); He & Feng (2007 ).

Experimental

Crystal data

[Zn(C₈H₅NO₅)(H₂O)₅]·H₂O
M_r = 368.60
Monoclinic, P 2₁ /c
a = 10.9584 (4) Å
b = 7.5548 (4) Å
c = 16.6510 (7) Å
β = 103.498 (3)°
V = 1340.43 (10) Å³
Z = 4
Mo Kα radiation
μ = 1.89 mm⁻¹
T = 293 K
0.36 × 0.09 × 0.05 mm

Data collection

Bruker APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.824, T_max = 0.918
19343 measured reflections
3086 independent reflections
2233 reflections with I > 2σ(I)
R_int = 0.100

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.084
S = 1.00
3086 reflections
226 parameters
18 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.48 e Å⁻³
Δρ_min = −0.80 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1WA⋯O2ⁱ	0.83 (2)	2.25 (2)	2.972 (3)	145 (3)
O1W—H1WB⋯O2Wⁱⁱ	0.81 (2)	2.58 (3)	3.118 (3)	125 (3)
O2W—H2WA⋯O4ⁱⁱⁱ	0.83 (2)	1.89 (2)	2.716 (2)	169 (3)
O2W—H2WB⋯O2ⁱ	0.80 (2)	1.96 (2)	2.742 (2)	163 (2)
O3W—H3WA⋯O2^iv	0.81 (2)	1.89 (2)	2.701 (2)	173 (2)
O3W—H3WB⋯O4^v	0.82 (2)	2.04 (2)	2.849 (2)	170 (3)
O4W—H4WA⋯O5^vi	0.82 (2)	2.02 (2)	2.810 (2)	160 (3)
O5W—H5WA⋯O1ⁱⁱⁱ	0.82 (2)	1.90 (2)	2.705 (2)	166 (3)
O5W—H5WB⋯O1^iv	0.81 (2)	1.95 (2)	2.742 (2)	164 (3)
O6W—H6WB⋯O3^v	0.82 (2)	1.89 (2)	2.697 (3)	171 (3)
Symmetry codes: (i) $[x+1, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) -x, -y, -z+1; (iii) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iv) $[x+1, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (v) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (vi) -x, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2006 ); cell refinement: SAINT (Bruker, 2006); 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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810017538/is2541sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810017538/is2541Isup2.hkl

checkCIF report

Comment top

The pyridinium carboxylate ligands, containing both of carboxylate and quaternary ammonium groups, have been extensively employed to design and construct novel complexes due to its versatile coordination behavior to metal ions (Zhang et al., 2003; Szafran et al., 2006; Yang et al., 2010). Herein, we report the synthesis and crystal structure of a new complex, [ZnL(H₂O)₅].H₂O (LH₂ = 5-carboxy-1-carboxymethyl-2-oxidopyridinium; He & Feng, 2007).

As shown in Fig. 1, the metal center Zn^II atom is six-coordinated by one O atom from one L^2- ligand [Zn—O 2.1039 (16) Å] and five water molecules [Zn—O 2.0554 (17)–2.0988 (19) Å], to form a distorted octahdral geometry. Notably, only one O atom from the flexible carboxylic groups of L^2- ligand coordinates to the Zn^II ion. As shown in Fig. 2, the complexes connected with each other by the O—H···O hydrogen bonds generate a three-dimensional structure.

Related literature top

For related structures, see: Jiang et al. (2009); Szafran et al. (2006); Yang et al. (2010); Zhang et al. (2003); He & Feng (2007).

Experimental top

All the starting materials and solvents were obtained commercially and were used without further purification. A mixture of N-carboxymethyl-2-oxo-pyridine-5-carboxylic acid (0.1972 g, 1 mmol), ZnNO₃ (0.1901 g, 1 mmol), and purified water (15 ml) was sealed in a 25 ml stainless steel reactor and kept at 393 K for 3 d. Then, the reactor was cooled to room temperature at a speed of 5 K/h. A large quantity of colorless single crystals were filtered out of the mixture with the yield of 85%.

Computing details top

Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT (Bruker, 2006); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound, with 30% probability displacement ellipsoids.
	Fig. 2. Three-dimensional framework with hydrogen bonding interactions.

Pentaaqua[2-(5-carboxylato-2-oxido-1-pyridinio)acetato]zinc(II) monohydrate top

Crystal data top

[Zn(C₈H₅NO₅)(H₂O)₅]·H₂O	F(000) = 760
M_r = 368.60	D_x = 1.826 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6642 reflections
a = 10.9584 (4) Å	θ = 1.9–27.6°
b = 7.5548 (4) Å	µ = 1.89 mm⁻¹
c = 16.6510 (7) Å	T = 293 K
β = 103.498 (3)°	Prism, colourless
V = 1340.43 (10) Å³	0.36 × 0.09 × 0.05 mm
Z = 4

Data collection top

Bruker APEXII area-detector diffractometer	3086 independent reflections
Radiation source: fine-focus sealed tube	2233 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.100
ω scans	θ_max = 27.6°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −14→14
T_min = 0.824, T_max = 0.918	k = −9→8
19343 measured reflections	l = −21→19

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.084	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ²(F_o²) + (0.0382P)²] where P = (F_o² + 2F_c²)/3
3086 reflections	(Δ/σ)_max < 0.001
226 parameters	Δρ_max = 0.48 e Å⁻³
18 restraints	Δρ_min = −0.80 e Å⁻³

Crystal data top

[Zn(C₈H₅NO₅)(H₂O)₅]·H₂O	V = 1340.43 (10) Å³
M_r = 368.60	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.9584 (4) Å	µ = 1.89 mm⁻¹
b = 7.5548 (4) Å	T = 293 K
c = 16.6510 (7) Å	0.36 × 0.09 × 0.05 mm
β = 103.498 (3)°

Data collection top

Bruker APEXII area-detector diffractometer	3086 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2233 reflections with I > 2σ(I)
T_min = 0.824, T_max = 0.918	R_int = 0.100
19343 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	18 restraints
wR(F²) = 0.084	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	Δρ_max = 0.48 e Å⁻³
3086 reflections	Δρ_min = −0.80 e Å⁻³
226 parameters

Special details top

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 > 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	0.14951 (2)	0.39964 (4)	0.404996 (17)	0.02275 (11)
O1	−0.56142 (14)	0.8182 (2)	0.07024 (11)	0.0314 (4)
O1W	0.0969 (2)	0.0417 (3)	0.59084 (15)	0.0564 (6)
H1WA	0.1593 (19)	−0.021 (4)	0.592 (2)	0.068*
H1WB	0.038 (2)	−0.002 (4)	0.5579 (17)	0.068*
O2	−0.70407 (16)	0.6153 (2)	0.01860 (11)	0.0357 (5)
O2W	0.16338 (18)	0.1231 (2)	0.40753 (11)	0.0324 (5)
H2WA	0.149 (2)	0.061 (3)	0.3650 (11)	0.039*
H2WB	0.207 (2)	0.071 (3)	0.4456 (11)	0.039*
O3	−0.30374 (16)	0.1584 (2)	0.26291 (11)	0.0322 (4)
O3W	0.13340 (17)	0.6755 (3)	0.41312 (11)	0.0331 (5)
H3WA	0.183 (2)	0.732 (3)	0.4479 (12)	0.040*
H3WB	0.120 (2)	0.730 (3)	0.3697 (10)	0.040*
O4	−0.08994 (16)	0.4075 (2)	0.22554 (10)	0.0290 (4)
O4W	0.12338 (18)	0.3724 (2)	0.52419 (11)	0.0306 (4)
H4WA	0.092 (2)	0.452 (2)	0.5466 (16)	0.037*
H4WB	0.103 (2)	0.276 (2)	0.5380 (16)	0.037*
O5	−0.04711 (15)	0.3999 (2)	0.36330 (10)	0.0263 (4)
O5W	0.33859 (16)	0.4349 (3)	0.45253 (12)	0.0348 (5)
H5WA	0.400 (2)	0.396 (3)	0.4376 (16)	0.042*
H5WB	0.357 (2)	0.520 (3)	0.4830 (15)	0.042*
O6W	0.17072 (18)	0.3938 (2)	0.28435 (11)	0.0302 (4)
H6WB	0.2178 (19)	0.467 (3)	0.2718 (16)	0.036*
H6WA	0.1020 (16)	0.399 (3)	0.2526 (15)	0.036*
N1	−0.34860 (18)	0.4432 (3)	0.22449 (12)	0.0223 (5)
C1	−0.4197 (2)	0.5668 (3)	0.17514 (15)	0.0233 (6)
H1A	−0.3972	0.6854	0.1826	0.028*
C2	−0.5222 (2)	0.5226 (3)	0.11561 (14)	0.0224 (5)
C3	−0.5541 (2)	0.3417 (3)	0.10731 (15)	0.0287 (6)
H3A	−0.6260	0.3074	0.0687	0.034*
C4	−0.4824 (2)	0.2166 (3)	0.15441 (15)	0.0279 (6)
H4A	−0.5046	0.0981	0.1462	0.033*
C5	−0.3744 (2)	0.2628 (3)	0.21590 (15)	0.0248 (6)
C6	−0.2487 (2)	0.4933 (3)	0.29580 (14)	0.0269 (6)
H6A	−0.2699	0.4489	0.3455	0.032*
H6B	−0.2454	0.6214	0.2996	0.032*
C7	−0.1195 (2)	0.4249 (3)	0.29292 (15)	0.0216 (5)
C8	−0.6009 (2)	0.6622 (3)	0.06435 (14)	0.0240 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.02172 (18)	0.0210 (2)	0.02425 (17)	0.00083 (12)	0.00280 (12)	−0.00019 (12)
O1	0.0270 (10)	0.0199 (11)	0.0432 (11)	−0.0037 (8)	−0.0001 (8)	0.0073 (9)
O1W	0.0464 (15)	0.0551 (16)	0.0705 (17)	0.0124 (12)	0.0194 (12)	0.0136 (13)
O2	0.0303 (11)	0.0272 (11)	0.0393 (11)	−0.0024 (8)	−0.0125 (8)	−0.0002 (8)
O2W	0.0466 (13)	0.0209 (11)	0.0242 (10)	0.0051 (8)	−0.0032 (9)	−0.0027 (8)
O3	0.0332 (10)	0.0268 (11)	0.0346 (10)	0.0082 (8)	0.0040 (8)	0.0064 (8)
O3W	0.0361 (11)	0.0223 (11)	0.0341 (11)	0.0003 (8)	−0.0053 (9)	−0.0004 (8)
O4	0.0275 (10)	0.0371 (11)	0.0215 (9)	0.0010 (8)	0.0042 (8)	0.0006 (8)
O4W	0.0394 (12)	0.0296 (12)	0.0237 (10)	0.0038 (9)	0.0093 (8)	−0.0017 (8)
O5	0.0196 (9)	0.0366 (11)	0.0205 (9)	0.0013 (7)	0.0003 (7)	0.0007 (8)
O5W	0.0203 (10)	0.0372 (13)	0.0448 (12)	0.0009 (8)	0.0036 (9)	−0.0134 (9)
O6W	0.0278 (11)	0.0356 (12)	0.0258 (10)	−0.0059 (8)	0.0035 (8)	0.0019 (8)
N1	0.0183 (11)	0.0221 (13)	0.0242 (11)	0.0009 (9)	0.0002 (8)	−0.0009 (9)
C1	0.0237 (14)	0.0203 (15)	0.0260 (13)	0.0004 (10)	0.0058 (11)	0.0006 (11)
C2	0.0210 (13)	0.0208 (14)	0.0239 (13)	0.0004 (11)	0.0026 (10)	−0.0001 (11)
C3	0.0243 (14)	0.0286 (16)	0.0298 (14)	−0.0037 (11)	−0.0004 (11)	−0.0039 (12)
C4	0.0286 (14)	0.0187 (14)	0.0339 (14)	−0.0023 (11)	0.0025 (11)	−0.0032 (12)
C5	0.0255 (13)	0.0245 (16)	0.0262 (13)	0.0031 (11)	0.0096 (11)	0.0031 (11)
C6	0.0263 (14)	0.0267 (16)	0.0247 (13)	0.0027 (12)	−0.0002 (11)	−0.0034 (11)
C7	0.0221 (13)	0.0142 (14)	0.0267 (13)	−0.0036 (10)	0.0021 (10)	−0.0005 (10)
C8	0.0225 (13)	0.0264 (16)	0.0223 (13)	0.0027 (11)	0.0034 (10)	0.0002 (11)

Geometric parameters (Å, º) top

Zn1—O5W	2.0554 (17)	O5W—H5WA	0.821 (16)
Zn1—O6W	2.0759 (18)	O5W—H5WB	0.812 (16)
Zn1—O4W	2.0805 (18)	O6W—H6WB	0.816 (15)
Zn1—O2W	2.0945 (18)	O6W—H6WA	0.814 (16)
Zn1—O3W	2.0988 (19)	N1—C1	1.362 (3)
Zn1—O5	2.1039 (16)	N1—C5	1.392 (3)
O1—C8	1.251 (3)	N1—C6	1.464 (3)
O1W—H1WA	0.829 (17)	C1—C2	1.355 (3)
O1W—H1WB	0.812 (17)	C1—H1A	0.9300
O2—C8	1.257 (3)	C2—C3	1.409 (4)
O2W—H2WA	0.832 (15)	C2—C8	1.498 (3)
O2W—H2WB	0.802 (15)	C3—C4	1.356 (3)
O3—C5	1.246 (3)	C3—H3A	0.9300
O3W—H3WA	0.813 (15)	C4—C5	1.416 (3)
O3W—H3WB	0.816 (15)	C4—H4A	0.9300
O4—C7	1.245 (3)	C6—C7	1.518 (3)
O4W—H4WA	0.823 (15)	C6—H6A	0.9700
O4W—H4WB	0.809 (15)	C6—H6B	0.9700
O5—C7	1.267 (3)

O5W—Zn1—O6W	92.57 (8)	H6WB—O6W—H6WA	110 (2)
O5W—Zn1—O4W	89.79 (8)	C1—N1—C5	122.35 (19)
O6W—Zn1—O4W	172.96 (8)	C1—N1—C6	121.7 (2)
O5W—Zn1—O2W	93.41 (8)	C5—N1—C6	115.59 (19)
O6W—Zn1—O2W	88.53 (7)	C2—C1—N1	122.1 (2)
O4W—Zn1—O2W	84.70 (7)	C2—C1—H1A	118.9
O5W—Zn1—O3W	86.50 (7)	N1—C1—H1A	118.9
O6W—Zn1—O3W	96.52 (7)	C1—C2—C3	117.1 (2)
O4W—Zn1—O3W	90.25 (7)	C1—C2—C8	120.8 (2)
O2W—Zn1—O3W	174.95 (8)	C3—C2—C8	122.0 (2)
O5W—Zn1—O5	171.74 (7)	C4—C3—C2	121.5 (2)
O6W—Zn1—O5	91.03 (7)	C4—C3—H3A	119.3
O4W—Zn1—O5	87.51 (7)	C2—C3—H3A	119.3
O2W—Zn1—O5	94.10 (7)	C3—C4—C5	121.4 (2)
O3W—Zn1—O5	85.71 (6)	C3—C4—H4A	119.3
H1WA—O1W—H1WB	107 (3)	C5—C4—H4A	119.3
Zn1—O2W—H2WA	123.1 (17)	O3—C5—N1	118.3 (2)
Zn1—O2W—H2WB	122.1 (18)	O3—C5—C4	126.2 (2)
H2WA—O2W—H2WB	111 (2)	N1—C5—C4	115.5 (2)
Zn1—O3W—H3WA	120.8 (18)	N1—C6—C7	114.4 (2)
Zn1—O3W—H3WB	116.6 (19)	N1—C6—H6A	108.7
H3WA—O3W—H3WB	109 (2)	C7—C6—H6A	108.7
Zn1—O4W—H4WA	121.7 (18)	N1—C6—H6B	108.7
Zn1—O4W—H4WB	118.0 (19)	C7—C6—H6B	108.7
H4WA—O4W—H4WB	111 (2)	H6A—C6—H6B	107.6
C7—O5—Zn1	132.66 (16)	O4—C7—O5	125.4 (2)
Zn1—O5W—H5WA	131.2 (19)	O4—C7—C6	120.3 (2)
Zn1—O5W—H5WB	114.9 (18)	O5—C7—C6	114.1 (2)
H5WA—O5W—H5WB	112 (2)	O1—C8—O2	124.0 (2)
Zn1—O6W—H6WB	117.0 (19)	O1—C8—C2	118.4 (2)
Zn1—O6W—H6WA	109.4 (19)	O2—C8—C2	117.6 (2)

O5W—Zn1—O5—C7	103.1 (5)	C1—N1—C5—C4	−2.3 (3)
O6W—Zn1—O5—C7	−12.8 (2)	C6—N1—C5—C4	171.2 (2)
O4W—Zn1—O5—C7	174.1 (2)	C3—C4—C5—O3	178.9 (2)
O2W—Zn1—O5—C7	−101.4 (2)	C3—C4—C5—N1	0.5 (4)
O3W—Zn1—O5—C7	83.6 (2)	C1—N1—C6—C7	−121.4 (2)
C5—N1—C1—C2	1.6 (4)	C5—N1—C6—C7	65.1 (3)
C6—N1—C1—C2	−171.5 (2)	Zn1—O5—C7—O4	21.6 (4)
N1—C1—C2—C3	1.0 (3)	Zn1—O5—C7—C6	−154.06 (16)
N1—C1—C2—C8	177.9 (2)	N1—C6—C7—O4	32.4 (3)
C1—C2—C3—C4	−2.8 (4)	N1—C6—C7—O5	−151.6 (2)
C8—C2—C3—C4	−179.6 (2)	C1—C2—C8—O1	9.1 (3)
C2—C3—C4—C5	2.1 (4)	C3—C2—C8—O1	−174.2 (2)
C1—N1—C5—O3	179.1 (2)	C1—C2—C8—O2	−170.0 (2)
C6—N1—C5—O3	−7.4 (3)	C3—C2—C8—O2	6.7 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WA···O2ⁱ	0.83 (2)	2.25 (2)	2.972 (3)	145 (3)
O1W—H1WB···O2Wⁱⁱ	0.81 (2)	2.58 (3)	3.118 (3)	125 (3)
O2W—H2WA···O4ⁱⁱⁱ	0.83 (2)	1.89 (2)	2.716 (2)	169 (3)
O2W—H2WB···O2ⁱ	0.80 (2)	1.96 (2)	2.742 (2)	163 (2)
O3W—H3WA···O2^iv	0.81 (2)	1.89 (2)	2.701 (2)	173 (2)
O3W—H3WB···O4^v	0.82 (2)	2.04 (2)	2.849 (2)	170 (3)
O4W—H4WA···O5^vi	0.82 (2)	2.02 (2)	2.810 (2)	160 (3)
O5W—H5WA···O1ⁱⁱⁱ	0.82 (2)	1.90 (2)	2.705 (2)	166 (3)
O5W—H5WB···O1^iv	0.81 (2)	1.95 (2)	2.742 (2)	164 (3)
O6W—H6WB···O3^v	0.82 (2)	1.89 (2)	2.697 (3)	171 (3)

Symmetry codes: (i) x+1, −y+1/2, z+1/2; (ii) −x, −y, −z+1; (iii) −x, y−1/2, −z+1/2; (iv) x+1, −y+3/2, z+1/2; (v) −x, y+1/2, −z+1/2; (vi) −x, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	[Zn(C₈H₅NO₅)(H₂O)₅]·H₂O
M_r	368.60
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	10.9584 (4), 7.5548 (4), 16.6510 (7)
β (°)	103.498 (3)
V (Å³)	1340.43 (10)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.89
Crystal size (mm)	0.36 × 0.09 × 0.05

Data collection
Diffractometer	Bruker APEXII area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.824, 0.918
No. of measured, independent and observed [I > 2σ(I)] reflections	19343, 3086, 2233
R_int	0.100
(sin θ/λ)_max (Å⁻¹)	0.651

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.084, 1.00
No. of reflections	3086
No. of parameters	226
No. of restraints	18
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.48, −0.80

Computer programs: APEX2 (Bruker, 2006), SAINT (Bruker, 2006), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WA···O2ⁱ	0.829 (17)	2.25 (2)	2.972 (3)	145 (3)
O1W—H1WB···O2Wⁱⁱ	0.812 (17)	2.58 (3)	3.118 (3)	125 (3)
O2W—H2WA···O4ⁱⁱⁱ	0.832 (15)	1.894 (16)	2.716 (2)	169 (3)
O2W—H2WB···O2ⁱ	0.802 (15)	1.964 (18)	2.742 (2)	163 (2)
O3W—H3WA···O2^iv	0.813 (15)	1.892 (16)	2.701 (2)	173 (2)
O3W—H3WB···O4^v	0.816 (15)	2.042 (17)	2.849 (2)	170 (3)
O4W—H4WA···O5^vi	0.823 (15)	2.023 (18)	2.810 (2)	160 (3)
O5W—H5WA···O1ⁱⁱⁱ	0.821 (16)	1.900 (18)	2.705 (2)	166 (3)
O5W—H5WB···O1^iv	0.812 (16)	1.951 (18)	2.742 (2)	164 (3)
O6W—H6WB···O3^v	0.816 (15)	1.889 (17)	2.697 (3)	171 (3)

Symmetry codes: (i) x+1, −y+1/2, z+1/2; (ii) −x, −y, −z+1; (iii) −x, y−1/2, −z+1/2; (iv) x+1, −y+3/2, z+1/2; (v) −x, y+1/2, −z+1/2; (vi) −x, −y+1, −z+1.

References

Bruker (2006). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
He, Y.-H. & Feng, Y.-L. (2007). Acta Cryst. E63, o3422. Web of Science CSD CrossRef IUCr Journals Google Scholar
Jiang, M.-X., Feng, Y.-L., He, Y.-H. & Su, H. (2009). Inorg. Chim. Acta, 362, 2856–2860. Web of Science CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Szafran, M., Katrusiak, A., Koput, J. & Dega, S. Z. (2006). J. Mol. Struct. 784, 98–108. Web of Science CSD CrossRef CAS Google Scholar
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Volume 66| Part 7| July 2010| Page m759

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