Poly[triaqua­[μ4-3-(4-carboxyl­atophen­oxy)propionato-κ4O:O′:O′′:O′′′][μ3-3-(4-carboxyl­atophen­oxy)propionato-κ3O:O′:O′′]dizinc]

Gao, S.; Ng, S.W.

doi:10.1107/S1600536812003200

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 2| February 2012| Pages m223-m224

doi:10.1107/S1600536812003200

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Poly[triaqua[μ₄-3-(4-carboxylatophenoxy)propionato-κ⁴O:O′:O′′:O′′′][μ₃-3-(4-carboxylatophenoxy)propionato-κ³O:O′:O′′]dizinc]

Shan Gao ^a and Seik Weng Ng ^b,^c ^*

^aKey Laboratory of Functional Inorganic Material Chemistry, Ministry of Education, Heilongjiang University, Harbin 150080, People's Republic of China, ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and ^cChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 24 January 2012; accepted 25 January 2012; online 31 January 2012)

The coordination polymer [Zn₂(C₁₀H₈O₅)₂(H₂O)₃]_n adopts a layer structure in which the two independent Zn^II ions exist in trigonal–bipyramidal coordination geometries. One carboxylate dianion binds to a monoaqua-coordinated metal ion through the aliphatic carboxylate end and to the diaqua-coordinated metal ion through the aromatic carboxylate end; the other dianion binds in the reverse manner. Three of the four carboxylate ends of the two dianions are also engaged in bridging interactions; these lead to a layer structure parallel to (100). Adjacent layers are linked by O—H_water⋯O hydrogen bonds into a three-dimensional network.

Related literature

For the cobalt(II) derivative of 3-(4-carboxyphenoxy)propionic acid, see: Xiao et al. (2006 ).

Experimental

Crystal data

[Zn₂(C₁₀H₈O₅)₂(H₂O)₃]
M_r = 601.12
Triclinic, $[P \overline 1]$
a = 7.6518 (3) Å
b = 11.3553 (5) Å
c = 13.5294 (6) Å
α = 77.2436 (14)°
β = 85.6236 (13)°
γ = 73.3105 (13)°
V = 1098.13 (8) Å³
Z = 2
Mo Kα radiation
μ = 2.26 mm⁻¹
T = 293 K
0.17 × 0.13 × 0.11 mm

Data collection

Rigaku R-AXIS RAPID IP diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.700, T_max = 0.790
10809 measured reflections
4954 independent reflections
4160 reflections with I > 2σ(I)
R_int = 0.019

Refinement

R[F² > 2σ(F²)] = 0.026
wR(F²) = 0.074
S = 1.04
4954 reflections
334 parameters
9 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.45 e Å⁻³
Δρ_min = −0.45 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H11⋯O4ⁱ	0.83 (1)	1.99 (1)	2.781 (2)	159 (2)
O1W—H12⋯O4ⁱⁱ	0.83 (1)	1.94 (1)	2.768 (2)	173 (2)
O2W—H21⋯O4ⁱⁱⁱ	0.83 (1)	2.13 (2)	2.854 (2)	145 (2)
O2W—H22⋯O7^iv	0.84 (1)	1.98 (1)	2.776 (2)	158 (2)
O3W—H31⋯O2^v	0.83 (1)	1.91 (2)	2.700 (2)	158 (3)
O3W—H32⋯O9^vi	0.84 (1)	2.31 (2)	3.026 (2)	143 (3)
Symmetry codes: (i) x+1, y, z-1; (ii) -x+1, -y+2, -z+1; (iii) x, y, z-1; (iv) -x+1, -y+1, -z+1; (v) -x, -y+2, -z+1; (vi) x-1, y, z+1.

Data collection: RAPID-AUTO (Rigaku, 1998 ); cell refinement: RAPID-AUTO; data reduction: CrystalClear (Rigaku, 2002 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812003200/bt5797sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812003200/bt5797Isup2.hkl

checkCIF report

Comment top

We reported the crystal structure of 3-(4-carboxyphenoxy)propropionic acid. We also reported the crystal structures of some metal derivatives. In the water-coordinated cobalt(II) derivative, two tetraaquacobalt cations are bridged by two 3-(4-carboxylatophenoxy)propionate dianions across a center of inversion to form a dinuclear molecule (Xiao et al., 2006). The title coordination polymer (Scheme I) adopts a layer structure in which the two independent Zn^II atoms exist in trigonal bipyramidal geometries. One carboxylate dianion binds to a mono-aqua coordinated metal atom through the aliphatic carboxyl end and to the di-aqua coordinated metal atom through the aromatic carboxyl end; the other dianion binds in the reverse manner (Fig.1). Three of the four carboxyl ends of the two dianions are also engaged in bridging interactions; these lead to a layer structure. Adjacent layers are linked by O–H_water···O hydrogen bonds into a three-dimensional network (Table 1).

Related literature top

For the cobalt(II) derivative of 3-(4-carboxyphenoxy)propionic acid, see: Xiao et al. (2006).

Experimental top

Zinc acetate (1 mmol) and 3-(4-carboxyphenoxy)propionic acid (1 mmol) were dissolved in water (10 ml). Sodium hydroxide (1 M) was added in drops until the solution registered a pH of 7. The solution was then set aside for the growth of colorless crystals.

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 1998); data reduction: CrystalClear (Rigaku, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

Fig. 1. Anisotropic displacement ellipsoid plot (Barbour, 2001) of a portion of polymeric [Zn₂(H₂O)₃(C₁₀H₈O₅)₂]_n at the 50% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

Poly[triaqua[µ₄-3-(4-carboxylatophenoxy)propionato- κ⁴O:O':O'':O'''][µ₃-3-(4- carboxylatophenoxy)propionato-κ³O:O':O'']dizinc] top

Crystal data top

[Zn₂(C₁₀H₈O₅)₂(H₂O)₃]	Z = 2
M_r = 601.12	F(000) = 612
Triclinic, P1	D_x = 1.818 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.6518 (3) Å	Cell parameters from 8993 reflections
b = 11.3553 (5) Å	θ = 3.1–27.5°
c = 13.5294 (6) Å	µ = 2.26 mm⁻¹
α = 77.2436 (14)°	T = 293 K
β = 85.6236 (13)°	Prism, colorless
γ = 73.3105 (13)°	0.17 × 0.13 × 0.11 mm
V = 1098.13 (8) Å³

Data collection top

Rigaku R-AXIS RAPID IP diffractometer	4954 independent reflections
Radiation source: fine-focus sealed tube	4160 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.019
ω scan	θ_max = 27.5°, θ_min = 3.1°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −9→9
T_min = 0.700, T_max = 0.790	k = −14→14
10809 measured reflections	l = −17→17

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)] = 0.026	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.074	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0397P)² + 0.4093P] where P = (F_o² + 2F_c²)/3
4954 reflections	(Δ/σ)_max = 0.001
334 parameters	Δρ_max = 0.45 e Å⁻³
9 restraints	Δρ_min = −0.45 e Å⁻³

Crystal data top

[Zn₂(C₁₀H₈O₅)₂(H₂O)₃]	γ = 73.3105 (13)°
M_r = 601.12	V = 1098.13 (8) Å³
Triclinic, P1	Z = 2
a = 7.6518 (3) Å	Mo Kα radiation
b = 11.3553 (5) Å	µ = 2.26 mm⁻¹
c = 13.5294 (6) Å	T = 293 K
α = 77.2436 (14)°	0.17 × 0.13 × 0.11 mm
β = 85.6236 (13)°

Data collection top

Rigaku R-AXIS RAPID IP diffractometer	4954 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	4160 reflections with I > 2σ(I)
T_min = 0.700, T_max = 0.790	R_int = 0.019
10809 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.026	9 restraints
wR(F²) = 0.074	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.45 e Å⁻³
4954 reflections	Δρ_min = −0.45 e Å⁻³
334 parameters

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

	x	y	z	U_iso*/U_eq
Zn1	0.63992 (3)	0.83763 (2)	0.070119 (16)	0.02491 (8)
Zn2	0.26901 (4)	0.60896 (2)	0.918931 (17)	0.03034 (8)
O1	0.54606 (19)	0.99522 (13)	0.12262 (11)	0.0303 (3)
O2	0.3096 (2)	1.16123 (14)	0.07830 (10)	0.0327 (3)
O3	0.1731 (2)	1.04925 (14)	0.55209 (10)	0.0362 (4)
O4	0.1231 (2)	0.89307 (14)	0.90191 (11)	0.0338 (3)
O5	0.2209 (2)	0.75470 (14)	0.80329 (11)	0.0367 (4)
O6	0.5517 (2)	0.57863 (14)	0.89038 (11)	0.0354 (4)
O7	0.7337 (2)	0.38375 (14)	0.93679 (10)	0.0340 (3)
O8	0.8141 (2)	0.43774 (14)	0.46231 (10)	0.0385 (4)
O9	0.7217 (2)	0.55924 (13)	0.10884 (11)	0.0329 (3)
O10	0.7013 (2)	0.70540 (13)	0.19529 (11)	0.0324 (3)
O1W	0.9003 (2)	0.86744 (15)	0.07296 (12)	0.0335 (3)
H11	0.959 (3)	0.860 (2)	0.0192 (13)	0.050*
H12	0.888 (4)	0.9382 (14)	0.0853 (18)	0.050*
O2W	0.3716 (2)	0.83032 (16)	0.06475 (12)	0.0380 (4)
H21	0.328 (4)	0.870 (2)	0.0085 (12)	0.057*
H22	0.361 (4)	0.7572 (12)	0.077 (2)	0.057*
O3W	−0.0265 (2)	0.62923 (17)	0.93647 (14)	0.0452 (4)
H31	−0.105 (3)	0.6968 (18)	0.9157 (19)	0.068*
H32	−0.048 (4)	0.600 (3)	0.9969 (10)	0.068*
C1	0.4045 (3)	1.07348 (18)	0.14434 (14)	0.0234 (4)
C2	0.3465 (3)	1.06585 (18)	0.25246 (14)	0.0245 (4)
C3	0.2374 (3)	1.17051 (19)	0.28675 (15)	0.0279 (4)
H3	0.1999	1.2472	0.2413	0.033*
C4	0.1841 (3)	1.16205 (19)	0.38719 (15)	0.0298 (4)
H4	0.1133	1.2332	0.4092	0.036*
C5	0.2360 (3)	1.0472 (2)	0.45583 (15)	0.0281 (4)
C6	0.3438 (3)	0.9416 (2)	0.42285 (16)	0.0341 (5)
H6	0.3781	0.8646	0.4681	0.041*
C7	0.4005 (3)	0.9514 (2)	0.32176 (16)	0.0312 (5)
H7	0.4751	0.8810	0.3002	0.037*
C8	0.2217 (3)	0.93520 (19)	0.62779 (15)	0.0296 (4)
H8A	0.3531	0.9033	0.6343	0.036*
H8B	0.1750	0.8713	0.6108	0.036*
C9	0.1340 (3)	0.97182 (19)	0.72457 (15)	0.0286 (4)
H9A	0.1824	1.0365	0.7386	0.034*
H9B	0.0040	1.0082	0.7139	0.034*
C10	0.1618 (3)	0.86549 (19)	0.81669 (14)	0.0246 (4)
C11	0.6559 (3)	0.4798 (2)	0.86980 (15)	0.0275 (4)
C12	0.6964 (3)	0.46932 (19)	0.76157 (14)	0.0267 (4)
C13	0.6249 (3)	0.57192 (19)	0.68433 (15)	0.0288 (4)
H13	0.5507	0.6458	0.7007	0.035*
C14	0.6621 (3)	0.5661 (2)	0.58321 (15)	0.0325 (5)
H14	0.6153	0.6361	0.5324	0.039*
C15	0.7701 (3)	0.4548 (2)	0.55855 (15)	0.0288 (4)
C16	0.8419 (3)	0.3509 (2)	0.63521 (16)	0.0335 (5)
H16	0.9131	0.2762	0.6187	0.040*
C17	0.8074 (3)	0.3587 (2)	0.73571 (15)	0.0318 (5)
H17	0.8584	0.2899	0.7866	0.038*
C18	0.7454 (3)	0.54209 (19)	0.38040 (14)	0.0294 (4)
H18A	0.7940	0.6114	0.3831	0.035*
H18B	0.6133	0.5708	0.3838	0.035*
C19	0.8078 (3)	0.49400 (19)	0.28414 (14)	0.0278 (4)
H19A	0.9401	0.4677	0.2815	0.033*
H19B	0.7653	0.4210	0.2854	0.033*
C20	0.7379 (3)	0.59226 (18)	0.18999 (14)	0.0226 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.03290 (14)	0.02110 (12)	0.01676 (12)	−0.00311 (9)	0.00282 (9)	−0.00263 (9)
Zn2	0.04902 (16)	0.02167 (13)	0.01550 (12)	−0.00240 (10)	−0.00106 (10)	−0.00351 (9)
O1	0.0326 (8)	0.0254 (7)	0.0311 (8)	−0.0037 (6)	0.0074 (6)	−0.0105 (6)
O2	0.0363 (8)	0.0361 (8)	0.0169 (7)	0.0019 (6)	0.0014 (6)	−0.0039 (6)
O3	0.0516 (10)	0.0296 (8)	0.0173 (7)	−0.0020 (7)	0.0065 (6)	0.0012 (6)
O4	0.0487 (9)	0.0341 (8)	0.0196 (7)	−0.0153 (7)	0.0066 (6)	−0.0047 (6)
O5	0.0563 (10)	0.0235 (7)	0.0211 (7)	−0.0011 (7)	0.0014 (7)	0.0002 (6)
O6	0.0450 (9)	0.0317 (8)	0.0274 (8)	−0.0068 (7)	0.0057 (7)	−0.0088 (6)
O7	0.0493 (9)	0.0333 (8)	0.0146 (7)	−0.0046 (7)	0.0004 (6)	−0.0044 (6)
O8	0.0595 (10)	0.0306 (8)	0.0141 (7)	0.0012 (7)	0.0011 (7)	0.0001 (6)
O9	0.0518 (9)	0.0240 (7)	0.0197 (7)	−0.0048 (7)	−0.0053 (6)	−0.0037 (6)
O10	0.0538 (9)	0.0205 (7)	0.0219 (7)	−0.0101 (6)	−0.0048 (7)	−0.0007 (6)
O1W	0.0325 (8)	0.0375 (9)	0.0313 (8)	−0.0102 (7)	0.0100 (6)	−0.0117 (7)
O2W	0.0416 (9)	0.0407 (9)	0.0327 (9)	−0.0189 (8)	−0.0044 (7)	0.0014 (7)
O3W	0.0379 (9)	0.0383 (10)	0.0460 (11)	−0.0004 (7)	0.0048 (8)	0.0038 (8)
C1	0.0284 (10)	0.0228 (9)	0.0205 (9)	−0.0086 (8)	0.0031 (8)	−0.0068 (7)
C2	0.0279 (10)	0.0259 (10)	0.0179 (9)	−0.0056 (8)	0.0015 (7)	−0.0036 (7)
C3	0.0372 (11)	0.0221 (9)	0.0198 (9)	−0.0042 (8)	0.0003 (8)	−0.0004 (7)
C4	0.0398 (11)	0.0230 (10)	0.0214 (10)	−0.0017 (8)	0.0026 (8)	−0.0039 (8)
C5	0.0333 (11)	0.0305 (11)	0.0172 (9)	−0.0071 (8)	0.0017 (8)	−0.0013 (8)
C6	0.0440 (13)	0.0238 (10)	0.0244 (10)	−0.0011 (9)	0.0019 (9)	0.0041 (8)
C7	0.0356 (11)	0.0246 (10)	0.0261 (10)	0.0003 (8)	0.0042 (9)	−0.0031 (8)
C8	0.0382 (11)	0.0270 (10)	0.0181 (9)	−0.0056 (9)	0.0010 (8)	0.0016 (8)
C9	0.0370 (11)	0.0249 (10)	0.0197 (9)	−0.0068 (8)	0.0014 (8)	0.0012 (8)
C10	0.0265 (10)	0.0272 (10)	0.0187 (9)	−0.0083 (8)	0.0011 (7)	−0.0009 (8)
C11	0.0335 (10)	0.0298 (10)	0.0196 (9)	−0.0101 (8)	0.0021 (8)	−0.0051 (8)
C12	0.0338 (11)	0.0292 (10)	0.0164 (9)	−0.0092 (8)	0.0012 (8)	−0.0033 (8)
C13	0.0363 (11)	0.0243 (10)	0.0231 (10)	−0.0049 (8)	0.0004 (8)	−0.0042 (8)
C14	0.0469 (13)	0.0271 (10)	0.0183 (9)	−0.0057 (9)	−0.0013 (9)	0.0003 (8)
C15	0.0392 (11)	0.0289 (10)	0.0165 (9)	−0.0079 (9)	0.0005 (8)	−0.0028 (8)
C16	0.0436 (12)	0.0276 (11)	0.0218 (10)	−0.0006 (9)	0.0022 (9)	−0.0027 (8)
C17	0.0392 (12)	0.0283 (11)	0.0204 (10)	−0.0017 (9)	−0.0007 (9)	0.0005 (8)
C18	0.0416 (12)	0.0264 (10)	0.0158 (9)	−0.0068 (9)	−0.0003 (8)	0.0005 (8)
C19	0.0395 (11)	0.0228 (10)	0.0166 (9)	−0.0051 (8)	−0.0003 (8)	0.0006 (7)
C20	0.0267 (9)	0.0236 (9)	0.0155 (8)	−0.0071 (7)	0.0032 (7)	−0.0010 (7)

Geometric parameters (Å, º) top

Zn1—O1	1.9919 (14)	C2—C7	1.397 (3)
Zn1—O2ⁱ	2.0136 (14)	C3—C4	1.379 (3)
Zn1—O10	1.9840 (14)	C3—H3	0.9300
Zn1—O1W	2.1188 (15)	C4—C5	1.395 (3)
Zn1—O2W	2.0855 (16)	C4—H4	0.9300
Zn2—O5	1.9791 (14)	C5—C6	1.389 (3)
Zn2—O6	2.1093 (16)	C6—C7	1.393 (3)
Zn2—O9ⁱⁱ	2.0073 (15)	C6—H6	0.9300
Zn2—O7ⁱⁱⁱ	1.9702 (14)	C7—H7	0.9300
Zn2—O3W	2.2055 (17)	C8—C9	1.511 (3)
O1—C1	1.250 (2)	C8—H8A	0.9700
O2—C1	1.268 (2)	C8—H8B	0.9700
O2—Zn1ⁱ	2.0136 (14)	C9—C10	1.512 (3)
O3—C5	1.356 (2)	C9—H9A	0.9700
O3—C8	1.435 (2)	C9—H9B	0.9700
O4—C10	1.253 (2)	C11—C12	1.497 (3)
O5—C10	1.258 (2)	C12—C13	1.390 (3)
O6—C11	1.250 (3)	C12—C17	1.399 (3)
O7—C11	1.280 (2)	C13—C14	1.388 (3)
O7—Zn2ⁱⁱⁱ	1.9702 (14)	C13—H13	0.9300
O8—C15	1.361 (2)	C14—C15	1.392 (3)
O8—C18	1.435 (2)	C14—H14	0.9300
O9—C20	1.261 (2)	C15—C16	1.394 (3)
O9—Zn2ⁱⁱ	2.0073 (15)	C16—C17	1.383 (3)
O10—C20	1.251 (2)	C16—H16	0.9300
O1W—H11	0.833 (9)	C17—H17	0.9300
O1W—H12	0.834 (9)	C18—C19	1.514 (3)
O2W—H21	0.832 (9)	C18—H18A	0.9700
O2W—H22	0.836 (10)	C18—H18B	0.9700
O3W—H31	0.833 (10)	C19—C20	1.512 (2)
O3W—H32	0.835 (10)	C19—H19A	0.9700
C1—C2	1.487 (3)	C19—H19B	0.9700
C2—C3	1.393 (3)

O10—Zn1—O1	103.22 (6)	C7—C6—H6	120.1
O10—Zn1—O2ⁱ	133.60 (6)	C6—C7—C2	120.67 (19)
O1—Zn1—O2ⁱ	122.33 (6)	C6—C7—H7	119.7
O10—Zn1—O2W	95.04 (7)	C2—C7—H7	119.7
O1—Zn1—O2W	88.80 (7)	O3—C8—C9	104.73 (16)
O2ⁱ—Zn1—O2W	94.31 (7)	O3—C8—H8A	110.8
O10—Zn1—O1W	89.29 (6)	C9—C8—H8A	110.8
O1—Zn1—O1W	85.51 (6)	O3—C8—H8B	110.8
O2ⁱ—Zn1—O1W	86.15 (6)	C9—C8—H8B	110.8
O2W—Zn1—O1W	173.51 (6)	H8A—C8—H8B	108.9
O7ⁱⁱⁱ—Zn2—O5	126.07 (6)	C10—C9—C8	115.08 (17)
O7ⁱⁱⁱ—Zn2—O9ⁱⁱ	115.44 (6)	C10—C9—H9A	108.5
O5—Zn2—O9ⁱⁱ	117.57 (6)	C8—C9—H9A	108.5
O7ⁱⁱⁱ—Zn2—O6	98.39 (6)	C10—C9—H9B	108.5
O5—Zn2—O6	89.55 (7)	C8—C9—H9B	108.5
O9ⁱⁱ—Zn2—O6	91.48 (6)	H9A—C9—H9B	107.5
O7ⁱⁱⁱ—Zn2—O3W	86.84 (7)	O4—C10—O5	123.89 (18)
O5—Zn2—O3W	89.82 (7)	O4—C10—C9	117.94 (18)
O9ⁱⁱ—Zn2—O3W	83.49 (7)	O5—C10—C9	118.18 (17)
O6—Zn2—O3W	173.95 (7)	O6—C11—O7	123.78 (18)
C1—O1—Zn1	144.10 (14)	O6—C11—C12	120.02 (18)
C1—O2—Zn1ⁱ	119.96 (13)	O7—C11—C12	116.20 (18)
C5—O3—C8	118.82 (16)	C13—C12—C17	118.71 (18)
C10—O5—Zn2	121.42 (13)	C13—C12—C11	119.70 (18)
C11—O6—Zn2	124.43 (15)	C17—C12—C11	121.58 (17)
C11—O7—Zn2ⁱⁱⁱ	121.58 (13)	C14—C13—C12	121.23 (19)
C15—O8—C18	117.79 (16)	C14—C13—H13	119.4
C20—O9—Zn2ⁱⁱ	131.33 (13)	C12—C13—H13	119.4
C20—O10—Zn1	119.49 (12)	C13—C14—C15	119.43 (18)
Zn1—O1W—H11	112.2 (19)	C13—C14—H14	120.3
Zn1—O1W—H12	109.3 (19)	C15—C14—H14	120.3
H11—O1W—H12	111.0 (16)	O8—C15—C14	124.62 (18)
Zn1—O2W—H21	109 (2)	O8—C15—C16	115.42 (18)
Zn1—O2W—H22	114 (2)	C14—C15—C16	119.96 (19)
H21—O2W—H22	110.4 (16)	C17—C16—C15	120.07 (19)
Zn2—O3W—H31	123 (2)	C17—C16—H16	120.0
Zn2—O3W—H32	108 (2)	C15—C16—H16	120.0
H31—O3W—H32	110.0 (16)	C16—C17—C12	120.56 (18)
O1—C1—O2	122.88 (18)	C16—C17—H17	119.7
O1—C1—C2	118.88 (17)	C12—C17—H17	119.7
O2—C1—C2	118.22 (17)	O8—C18—C19	105.89 (16)
C3—C2—C7	118.70 (18)	O8—C18—H18A	110.6
C3—C2—C1	121.49 (17)	C19—C18—H18A	110.6
C7—C2—C1	119.80 (18)	O8—C18—H18B	110.6
C4—C3—C2	120.90 (18)	C19—C18—H18B	110.6
C4—C3—H3	119.5	H18A—C18—H18B	108.7
C2—C3—H3	119.5	C20—C19—C18	112.35 (16)
C3—C4—C5	120.22 (19)	C20—C19—H19A	109.1
C3—C4—H4	119.9	C18—C19—H19A	109.1
C5—C4—H4	119.9	C20—C19—H19B	109.1
O3—C5—C6	125.13 (18)	C18—C19—H19B	109.1
O3—C5—C4	115.20 (18)	H19A—C19—H19B	107.9
C6—C5—C4	119.68 (18)	O10—C20—O9	122.00 (17)
C5—C6—C7	119.81 (18)	O10—C20—C19	117.89 (17)
C5—C6—H6	120.1	O9—C20—C19	120.09 (17)

O10—Zn1—O1—C1	−97.8 (2)	C5—O3—C8—C9	178.69 (18)
O2ⁱ—Zn1—O1—C1	91.4 (2)	O3—C8—C9—C10	178.60 (17)
O2W—Zn1—O1—C1	−3.0 (2)	Zn2—O5—C10—O4	−2.4 (3)
O1W—Zn1—O1—C1	173.9 (2)	Zn2—O5—C10—C9	178.16 (14)
O7ⁱⁱⁱ—Zn2—O5—C10	−9.1 (2)	C8—C9—C10—O4	166.79 (19)
O9ⁱⁱ—Zn2—O5—C10	159.36 (15)	C8—C9—C10—O5	−13.7 (3)
O6—Zn2—O5—C10	−109.21 (17)	Zn2—O6—C11—O7	−86.4 (2)
O3W—Zn2—O5—C10	76.81 (17)	Zn2—O6—C11—C12	93.8 (2)
O7ⁱⁱⁱ—Zn2—O6—C11	113.26 (16)	Zn2ⁱⁱⁱ—O7—C11—O6	−10.7 (3)
O5—Zn2—O6—C11	−120.30 (16)	Zn2ⁱⁱⁱ—O7—C11—C12	169.15 (14)
O9ⁱⁱ—Zn2—O6—C11	−2.73 (16)	O6—C11—C12—C13	3.2 (3)
O1—Zn1—O10—C20	168.90 (15)	O7—C11—C12—C13	−176.66 (19)
O2ⁱ—Zn1—O10—C20	−21.89 (19)	O6—C11—C12—C17	−177.8 (2)
O2W—Zn1—O10—C20	78.96 (16)	O7—C11—C12—C17	2.4 (3)
O1W—Zn1—O10—C20	−105.88 (16)	C17—C12—C13—C14	−0.2 (3)
Zn1—O1—C1—O2	−80.4 (3)	C11—C12—C13—C14	178.9 (2)
Zn1—O1—C1—C2	101.1 (2)	C12—C13—C14—C15	1.3 (3)
Zn1ⁱ—O2—C1—O1	10.1 (3)	C18—O8—C15—C14	0.4 (3)
Zn1ⁱ—O2—C1—C2	−171.43 (13)	C18—O8—C15—C16	−179.35 (19)
O1—C1—C2—C3	155.8 (2)	C13—C14—C15—O8	179.3 (2)
O2—C1—C2—C3	−22.7 (3)	C13—C14—C15—C16	−0.9 (3)
O1—C1—C2—C7	−24.7 (3)	O8—C15—C16—C17	179.2 (2)
O2—C1—C2—C7	156.8 (2)	C14—C15—C16—C17	−0.6 (4)
C7—C2—C3—C4	0.3 (3)	C15—C16—C17—C12	1.8 (4)
C1—C2—C3—C4	179.79 (19)	C13—C12—C17—C16	−1.4 (3)
C2—C3—C4—C5	−1.3 (3)	C11—C12—C17—C16	179.6 (2)
C8—O3—C5—C6	0.9 (3)	C15—O8—C18—C19	−177.33 (19)
C8—O3—C5—C4	−179.40 (19)	O8—C18—C19—C20	177.22 (17)
C3—C4—C5—O3	−178.8 (2)	Zn1—O10—C20—O9	−6.3 (3)
C3—C4—C5—C6	0.9 (3)	Zn1—O10—C20—C19	172.15 (13)
O3—C5—C6—C7	−179.8 (2)	Zn2ⁱⁱ—O9—C20—O10	−169.17 (15)
C4—C5—C6—C7	0.5 (3)	Zn2ⁱⁱ—O9—C20—C19	12.4 (3)
C5—C6—C7—C2	−1.5 (3)	C18—C19—C20—O10	25.9 (3)
C3—C2—C7—C6	1.1 (3)	C18—C19—C20—O9	−155.68 (19)
C1—C2—C7—C6	−178.4 (2)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H11···O4^iv	0.83 (1)	1.99 (1)	2.781 (2)	159 (2)
O1W—H12···O4^v	0.83 (1)	1.94 (1)	2.768 (2)	173 (2)
O2W—H21···O4^vi	0.83 (1)	2.13 (2)	2.854 (2)	145 (2)
O2W—H22···O7ⁱⁱ	0.84 (1)	1.98 (1)	2.776 (2)	158 (2)
O3W—H31···O2^vii	0.83 (1)	1.91 (2)	2.700 (2)	158 (3)
O3W—H32···O9^viii	0.84 (1)	2.31 (2)	3.026 (2)	143 (3)

Symmetry codes: (ii) −x+1, −y+1, −z+1; (iv) x+1, y, z−1; (v) −x+1, −y+2, −z+1; (vi) x, y, z−1; (vii) −x, −y+2, −z+1; (viii) x−1, y, z+1.

Experimental details

Crystal data
Chemical formula	[Zn₂(C₁₀H₈O₅)₂(H₂O)₃]
M_r	601.12
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	7.6518 (3), 11.3553 (5), 13.5294 (6)
α, β, γ (°)	77.2436 (14), 85.6236 (13), 73.3105 (13)
V (Å³)	1098.13 (8)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	2.26
Crystal size (mm)	0.17 × 0.13 × 0.11

Data collection
Diffractometer	Rigaku R-AXIS RAPID IP diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.700, 0.790
No. of measured, independent and observed [I > 2σ(I)] reflections	10809, 4954, 4160
R_int	0.019
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.026, 0.074, 1.04
No. of reflections	4954
No. of parameters	334
No. of restraints	9
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.45, −0.45

Computer programs: RAPID-AUTO (Rigaku, 1998), CrystalClear (Rigaku, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H11···O4ⁱ	0.83 (1)	1.99 (1)	2.781 (2)	159 (2)
O1W—H12···O4ⁱⁱ	0.83 (1)	1.94 (1)	2.768 (2)	173 (2)
O2W—H21···O4ⁱⁱⁱ	0.83 (1)	2.13 (2)	2.854 (2)	145 (2)
O2W—H22···O7^iv	0.84 (1)	1.98 (1)	2.776 (2)	158 (2)
O3W—H31···O2^v	0.83 (1)	1.91 (2)	2.700 (2)	158 (3)
O3W—H32···O9^vi	0.84 (1)	2.31 (2)	3.026 (2)	143 (3)

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

Acknowledgements

This work is supported by the Key Project of the Natural Science Foundation of Heilongjiang Province (grant No. ZD200903), the Key Project of the Education Bureau of Heilongjiang Province (grants No. 12511z023, No. 2011CJHB006), the Innovation Team of the Education Bureau of Heilongjiang Province (grant No. 2010 t d03), Heilongjiang University (grant No. Hdtd2010–04) and the Ministry of Higher Education of Malaysia (grant No. UM.C/HIR/MOHE/SC/12).

References

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Xiao, Y.-H., Gao, S. & Ng, S. W. (2006). Acta Cryst. E62, m2274–m2276. Web of Science CSD CrossRef IUCr Journals Google Scholar

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