Bis(acetato-κO)bis­(μ3-quinolin-8-olato-κ4N,O:O:O)tetra­kis(μ2-quinolin-8-olato-κ3N,O:O)tetra­zinc(II) dihydrate

Sattarzadeh, E.; Mohammadnezhad, G.; Amini, M.M.; Ng, S.W.

doi:10.1107/S1600536809020157

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 7| July 2009| Pages m712-m713

doi:10.1107/S1600536809020157

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Bis(acetato-κO)bis(μ₃-quinolin-8-olato-κ⁴N,O:O:O)tetrakis(μ₂-quinolin-8-olato-κ³N,O:O)tetrazinc(II) dihydrate

Elham Sattarzadeh,^a Gholamhossein Mohammadnezhad,^a Mostafa M. Amini ^a and Seik Weng Ng ^b ^*

^aDepartment of Chemistry, General Campus, Shahid Beheshti University, Tehran 1983963113, Iran, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 19 May 2009; accepted 27 May 2009; online 6 June 2009)

In the centrosymmetric title compound, [Zn₄(C₉H₆NO)₆(C₂H₃O₂)₂]·2H₂O, the Zn^II atom that is bonded to one O atom of the acetate group is chelated by a quinolin-8-olate anion. This Zn atom is also bonded to the oxide O atoms of two other quinolin-8-olate anions, which themselves engage in chelation to the other Zn^II atoms. The Zn^II atom is five-coordinate in a square-pyramidal coordination geometry. The second Zn^II atom is six-coordinate as it is linked to two oxide O atoms of the anions that chelate to the acetate-bound metal atom, and is chelated by two quinolin-8-olate ligands. The uncoordinated water molecule is disordered over two positions in a 4:1 ratio. O—H⋯O hydrogen bonds between the water molecules and the free O atoms of the carboxylate groups consolidate the crystal packing.

Related literature

For previous studies of the zinc derivatives of 8-hydroxyquinoline, see: Sattarzadeh et al. (2009a ,b ).

Experimental

Crystal data

[Zn₄(C₉H₆NO)₆(C₂H₃O₂)₂]·2H₂O
M_r = 1280.49
Triclinic, $[P \overline 1]$
a = 11.3313 (3) Å
b = 11.8367 (3) Å
c = 13.5379 (3) Å
α = 111.070 (2)°
β = 107.740 (2)°
γ = 112.579 (2)°
V = 1342.16 (6) Å³
Z = 1
Mo Kα radiation
μ = 1.84 mm⁻¹
T = 100 K
0.15 × 0.10 × 0.05 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.657, T_max = 0.746 (expected range = 0.803–0.912)
12632 measured reflections
6146 independent reflections
4418 reflections with I > 2σ(I)
R_int = 0.037

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.102
S = 1.00
6146 reflections
372 parameters
12 restraints
H-atom parameters constrained
Δρ_max = 0.63 e Å⁻³
Δρ_min = −0.44 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1w—H1w1⋯O4	0.84	2.04	2.858 (6)	166
O1w'—H1w3⋯O4	0.84	2.04	2.83 (2)	157

Data collection: APEX2 (Bruker, 2008 ); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; 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, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809020157/tk2455sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809020157/tk2455Isup2.hkl

checkCIF report

Related literature top

For previous studies of the zinc derivatives of 8-hydroxyquinoline, see: Sattarzadeh et al. (2009a,b).

Experimental top

Zinc acetate dihydrate (0.22 g, 0.1 mmol) and 2-methyl-8-hydroxyquinoline (0.14 g, 1 mmol) were loaded into a convection tube. The tube was filled with dry methanol and kept at 333 K. Crystals were collected from the side-arm after a week. The crystals are stable up to 573 K.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); 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, 2009).

Figures top

Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of [Zn₂(C₂H₃O₂)(C₉H₆NO)₃]₂^.2H₂O; ellipsoids are drawn at the 70% probability level and H atoms with an arbitrary radius. The disordered lattice water molecule is not shown.

Bis(acetato-κO)bis(µ₃-quinolin-8-olato- κ⁴N,O:O:O)tetrakis(µ₂-quinolin-8-olato- κ³N,O:O)tetrazinc(II) dihydrate top

Crystal data top

[Zn₄(C₉H₆NO)₆(C₂H₃O₂)₂]·2H₂O	Z = 1
M_r = 1280.49	F(000) = 652
Triclinic, P1	D_x = 1.584 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 11.3313 (3) Å	Cell parameters from 2730 reflections
b = 11.8367 (3) Å	θ = 2.3–26.7°
c = 13.5379 (3) Å	µ = 1.84 mm⁻¹
α = 111.070 (2)°	T = 100 K
β = 107.740 (2)°	Prism, yellow
γ = 112.579 (2)°	0.15 × 0.10 × 0.05 mm
V = 1342.16 (6) Å³

Data collection top

Bruker SMART APEX diffractometer	6146 independent reflections
Radiation source: fine-focus sealed tube	4418 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.037
ω scans	θ_max = 27.5°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −14→14
T_min = 0.657, T_max = 0.746	k = −15→15
12632 measured reflections	l = −17→16

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.102	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.0512P)²] where P = (F_o² + 2F_c²)/3
6146 reflections	(Δ/σ)_max = 0.001
372 parameters	Δρ_max = 0.63 e Å⁻³
12 restraints	Δρ_min = −0.44 e Å⁻³

Crystal data top

[Zn₄(C₉H₆NO)₆(C₂H₃O₂)₂]·2H₂O	γ = 112.579 (2)°
M_r = 1280.49	V = 1342.16 (6) Å³
Triclinic, P1	Z = 1
a = 11.3313 (3) Å	Mo Kα radiation
b = 11.8367 (3) Å	µ = 1.84 mm⁻¹
c = 13.5379 (3) Å	T = 100 K
α = 111.070 (2)°	0.15 × 0.10 × 0.05 mm
β = 107.740 (2)°

Data collection top

Bruker SMART APEX diffractometer	6146 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4418 reflections with I > 2σ(I)
T_min = 0.657, T_max = 0.746	R_int = 0.037
12632 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	12 restraints
wR(F²) = 0.102	H-atom parameters constrained
S = 1.00	Δρ_max = 0.63 e Å⁻³
6146 reflections	Δρ_min = −0.44 e Å⁻³
372 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.

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Zn1	0.73984 (4)	0.30627 (4)	0.26111 (3)	0.01608 (10)
Zn2	0.97306 (4)	0.63077 (4)	0.52018 (3)	0.01623 (10)
O1	0.8598 (2)	0.5204 (2)	0.32955 (19)	0.0198 (5)
O2	0.8541 (2)	0.4092 (2)	0.46797 (19)	0.0163 (4)
O3	0.8952 (2)	0.2597 (2)	0.28947 (19)	0.0186 (5)
O4	0.5060 (3)	0.3123 (3)	0.1537 (2)	0.0303 (6)
O5	0.6110 (2)	0.2083 (2)	0.0791 (2)	0.0209 (5)
O1W	0.5348 (9)	0.5762 (6)	0.1876 (6)	0.090 (3)	0.80 (2)
H1W1	0.5392	0.5080	0.1901	0.135*	0.80 (2)
H1W2	0.4513	0.5621	0.1737	0.135*	0.80 (2)
O1W'	0.463 (4)	0.542 (3)	0.223 (2)	0.092 (12)	0.20 (2)
H1W3	0.4545	0.4638	0.1826	0.139*	0.20 (2)
H1W4	0.4981	0.5977	0.2003	0.139*	0.20 (2)
N1	1.0559 (3)	0.8045 (3)	0.4946 (2)	0.0182 (6)
N2	0.5909 (3)	0.1627 (3)	0.2853 (2)	0.0178 (6)
N3	1.1687 (3)	0.3302 (3)	0.4247 (2)	0.0174 (6)
C1	1.1537 (3)	0.9450 (4)	0.5797 (3)	0.0232 (7)
H1A	1.1990	0.9756	0.6641	0.028*
C2	1.1928 (4)	1.0508 (4)	0.5495 (3)	0.0276 (8)
H2A	1.2638	1.1509	0.6124	0.033*
C3	1.1272 (4)	1.0069 (4)	0.4285 (4)	0.0284 (8)
H3	1.1520	1.0772	0.4069	0.034*
C4	1.0221 (4)	0.8573 (4)	0.3345 (3)	0.0241 (7)
C5	0.9514 (4)	0.8022 (4)	0.2072 (3)	0.0316 (8)
H5	0.9698	0.8670	0.1795	0.038*
C6	0.8564 (4)	0.6556 (4)	0.1240 (3)	0.0329 (9)
H6	0.8110	0.6192	0.0383	0.040*
C7	0.8239 (4)	0.5569 (4)	0.1620 (3)	0.0267 (8)
H7	0.7578	0.4554	0.1016	0.032*
C8	0.8863 (3)	0.6050 (3)	0.2849 (3)	0.0202 (7)
C9	0.9897 (3)	0.7585 (3)	0.3730 (3)	0.0177 (6)
C10	0.4661 (3)	0.0363 (4)	0.1931 (3)	0.0229 (7)
H10	0.4467	0.0028	0.1112	0.028*
C11	0.3616 (4)	−0.0494 (4)	0.2128 (3)	0.0258 (8)
H11	0.2737	−0.1402	0.1449	0.031*
C12	0.3862 (3)	−0.0027 (4)	0.3285 (3)	0.0234 (7)
H12	0.3139	−0.0592	0.3416	0.028*
C13	0.5199 (3)	0.1307 (3)	0.4303 (3)	0.0198 (7)
C14	0.5559 (4)	0.1872 (4)	0.5534 (3)	0.0237 (7)
H14	0.4878	0.1370	0.5730	0.028*
C15	0.6902 (4)	0.3157 (4)	0.6457 (3)	0.0233 (7)
H15	0.7142	0.3536	0.7290	0.028*
C16	0.7934 (3)	0.3927 (3)	0.6193 (3)	0.0196 (7)
H16	0.8864	0.4800	0.6852	0.024*
C17	0.7617 (3)	0.3435 (3)	0.5006 (3)	0.0164 (6)
C18	0.6216 (3)	0.2095 (3)	0.4029 (3)	0.0168 (6)
C19	1.3027 (3)	0.3629 (3)	0.4935 (3)	0.0228 (7)
H19	1.3424	0.4049	0.5797	0.027*
C20	1.3880 (4)	0.3375 (3)	0.4430 (3)	0.0234 (7)
H20	1.4818	0.3580	0.4943	0.028*
C21	1.3372 (4)	0.2840 (4)	0.3216 (3)	0.0265 (8)
H21	1.3965	0.2700	0.2881	0.032*
C22	1.1942 (4)	0.2489 (4)	0.2443 (3)	0.0250 (7)
C23	1.1331 (4)	0.1976 (5)	0.1187 (3)	0.0376 (10)
H23	1.1877	0.1843	0.0795	0.045*
C24	0.9941 (4)	0.1666 (5)	0.0524 (3)	0.0389 (10)
H24	0.9531	0.1312	−0.0330	0.047*
C25	0.9106 (4)	0.1857 (4)	0.1075 (3)	0.0282 (8)
H25	0.8143	0.1625	0.0588	0.034*
C26	0.9662 (3)	0.2371 (3)	0.2302 (3)	0.0197 (7)
C27	1.1122 (3)	0.2711 (3)	0.3013 (3)	0.0181 (6)
C28	0.5110 (4)	0.2375 (4)	0.0656 (3)	0.0255 (8)
C29	0.3962 (4)	0.1727 (5)	−0.0659 (4)	0.0422 (10)
H29A	0.3284	0.2048	−0.0657	0.063*
H29B	0.3393	0.0662	−0.1102	0.063*
H29C	0.4466	0.2050	−0.1070	0.063*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.01469 (19)	0.01421 (19)	0.0145 (2)	0.00664 (16)	0.00615 (15)	0.00615 (16)
Zn2	0.01675 (19)	0.01366 (19)	0.0148 (2)	0.00730 (16)	0.00658 (16)	0.00720 (16)
O1	0.0218 (11)	0.0119 (11)	0.0143 (11)	0.0041 (9)	0.0047 (9)	0.0067 (9)
O2	0.0158 (11)	0.0131 (11)	0.0192 (12)	0.0064 (9)	0.0102 (9)	0.0090 (9)
O3	0.0176 (11)	0.0180 (11)	0.0161 (12)	0.0093 (10)	0.0085 (9)	0.0065 (10)
O4	0.0328 (14)	0.0316 (14)	0.0345 (15)	0.0214 (12)	0.0194 (12)	0.0191 (12)
O5	0.0185 (11)	0.0206 (12)	0.0161 (12)	0.0101 (10)	0.0059 (9)	0.0071 (10)
O1W	0.094 (5)	0.061 (3)	0.112 (5)	0.056 (3)	0.039 (3)	0.041 (3)
O1W'	0.099 (15)	0.090 (13)	0.093 (14)	0.065 (11)	0.030 (7)	0.056 (9)
N1	0.0178 (13)	0.0154 (13)	0.0205 (14)	0.0095 (12)	0.0101 (12)	0.0084 (12)
N2	0.0173 (13)	0.0158 (13)	0.0177 (14)	0.0084 (11)	0.0081 (11)	0.0085 (12)
N3	0.0183 (13)	0.0129 (13)	0.0205 (14)	0.0084 (11)	0.0087 (12)	0.0099 (12)
C1	0.0205 (17)	0.0201 (17)	0.0247 (18)	0.0102 (15)	0.0117 (15)	0.0096 (15)
C2	0.0243 (18)	0.0160 (17)	0.039 (2)	0.0092 (15)	0.0188 (17)	0.0115 (16)
C3	0.0301 (19)	0.0231 (18)	0.046 (2)	0.0149 (16)	0.0276 (18)	0.0240 (18)
C4	0.0244 (17)	0.0251 (18)	0.034 (2)	0.0146 (15)	0.0196 (16)	0.0211 (17)
C5	0.039 (2)	0.037 (2)	0.034 (2)	0.0209 (19)	0.0246 (18)	0.0283 (19)
C6	0.039 (2)	0.037 (2)	0.023 (2)	0.0191 (19)	0.0151 (17)	0.0194 (18)
C7	0.0272 (18)	0.0253 (18)	0.0187 (18)	0.0090 (16)	0.0091 (15)	0.0124 (15)
C8	0.0214 (16)	0.0189 (16)	0.0221 (18)	0.0107 (14)	0.0125 (14)	0.0123 (15)
C9	0.0174 (15)	0.0175 (16)	0.0203 (17)	0.0107 (13)	0.0107 (14)	0.0100 (14)
C10	0.0193 (16)	0.0185 (17)	0.0210 (18)	0.0088 (14)	0.0048 (14)	0.0084 (14)
C11	0.0168 (16)	0.0160 (17)	0.029 (2)	0.0034 (14)	0.0040 (15)	0.0113 (15)
C12	0.0173 (16)	0.0220 (17)	0.035 (2)	0.0096 (14)	0.0136 (15)	0.0198 (16)
C13	0.0175 (16)	0.0202 (17)	0.0267 (19)	0.0114 (14)	0.0122 (14)	0.0155 (15)
C14	0.0224 (17)	0.0262 (18)	0.033 (2)	0.0139 (15)	0.0180 (16)	0.0213 (17)
C15	0.0298 (18)	0.0265 (18)	0.0239 (18)	0.0179 (16)	0.0168 (16)	0.0178 (16)
C16	0.0210 (16)	0.0167 (16)	0.0209 (17)	0.0102 (14)	0.0105 (14)	0.0103 (14)
C17	0.0195 (16)	0.0153 (15)	0.0210 (17)	0.0122 (14)	0.0114 (14)	0.0119 (14)
C18	0.0175 (15)	0.0154 (15)	0.0187 (17)	0.0110 (13)	0.0092 (13)	0.0084 (13)
C19	0.0178 (16)	0.0144 (16)	0.0244 (18)	0.0056 (14)	0.0040 (14)	0.0098 (14)
C20	0.0187 (16)	0.0166 (16)	0.034 (2)	0.0112 (14)	0.0107 (15)	0.0143 (15)
C21	0.0226 (17)	0.0216 (17)	0.036 (2)	0.0138 (15)	0.0168 (16)	0.0129 (16)
C22	0.0260 (18)	0.0200 (17)	0.029 (2)	0.0143 (15)	0.0157 (16)	0.0109 (15)
C23	0.035 (2)	0.053 (3)	0.029 (2)	0.029 (2)	0.0220 (19)	0.017 (2)
C24	0.033 (2)	0.058 (3)	0.019 (2)	0.026 (2)	0.0135 (17)	0.0129 (19)
C25	0.0234 (18)	0.036 (2)	0.0217 (19)	0.0177 (17)	0.0110 (15)	0.0113 (17)
C26	0.0194 (16)	0.0146 (16)	0.0211 (18)	0.0089 (14)	0.0096 (14)	0.0076 (14)
C27	0.0197 (16)	0.0125 (15)	0.0198 (17)	0.0086 (13)	0.0092 (14)	0.0079 (13)
C28	0.0226 (17)	0.0231 (18)	0.0262 (19)	0.0104 (15)	0.0105 (15)	0.0137 (16)
C29	0.031 (2)	0.050 (3)	0.035 (2)	0.023 (2)	0.0066 (18)	0.022 (2)

Geometric parameters (Å, º) top

Zn1—O5	2.000 (2)	C5—C6	1.364 (5)
Zn1—O1	2.007 (2)	C5—H5	0.9500
Zn1—O3	2.009 (2)	C6—C7	1.407 (5)
Zn1—N2	2.093 (3)	C6—H6	0.9500
Zn1—O2	2.265 (2)	C7—C8	1.374 (4)
Zn2—O1	2.070 (2)	C7—H7	0.9500
Zn2—O3ⁱ	2.078 (2)	C8—C9	1.433 (4)
Zn2—N3ⁱ	2.098 (3)	C10—C11	1.402 (5)
Zn2—N1	2.111 (3)	C10—H10	0.9500
Zn2—O2	2.137 (2)	C11—C12	1.353 (5)
Zn2—O2ⁱ	2.158 (2)	C11—H11	0.9500
O1—C8	1.331 (4)	C12—C13	1.419 (4)
O2—C17	1.341 (3)	C12—H12	0.9500
O2—Zn2ⁱ	2.158 (2)	C13—C14	1.403 (5)
O3—C26	1.329 (4)	C13—C18	1.421 (4)
O3—Zn2ⁱ	2.078 (2)	C14—C15	1.374 (5)
O4—C28	1.236 (4)	C14—H14	0.9500
O5—C28	1.288 (4)	C15—C16	1.412 (4)
O1W—H1W1	0.8399	C15—H15	0.9500
O1W—H1W2	0.8400	C16—C17	1.367 (4)
O1W—H1W3	1.2538	C16—H16	0.9500
O1W—H1W4	0.6012	C17—C18	1.437 (4)
O1W'—H1W1	1.2197	C19—C20	1.404 (5)
O1W'—H1W2	0.7744	C19—H19	0.9500
O1W'—H1W3	0.8400	C20—C21	1.352 (5)
O1W'—H1W4	0.8400	C20—H20	0.9500
N1—C1	1.322 (4)	C21—C22	1.425 (5)
N1—C9	1.364 (4)	C21—H21	0.9500
N2—C10	1.324 (4)	C22—C23	1.399 (5)
N2—C18	1.357 (4)	C22—C27	1.416 (4)
N3—C19	1.323 (4)	C23—C24	1.371 (5)
N3—C27	1.362 (4)	C23—H23	0.9500
N3—Zn2ⁱ	2.098 (3)	C24—C25	1.406 (5)
C1—C2	1.408 (5)	C24—H24	0.9500
C1—H1A	0.9500	C25—C26	1.367 (5)
C2—C3	1.363 (5)	C25—H25	0.9500
C2—H2A	0.9500	C26—C27	1.438 (4)
C3—C4	1.418 (5)	C28—C29	1.514 (5)
C3—H3	0.9500	C29—H29A	0.9800
C4—C5	1.409 (5)	C29—H29B	0.9800
C4—C9	1.414 (4)	C29—H29C	0.9800

O5—Zn1—O1	106.13 (9)	O1—C8—C7	125.4 (3)
O5—Zn1—O3	107.95 (9)	O1—C8—C9	116.9 (3)
O1—Zn1—O3	102.85 (9)	C7—C8—C9	117.7 (3)
O5—Zn1—N2	97.79 (9)	N1—C9—C4	121.8 (3)
O1—Zn1—N2	138.81 (10)	N1—C9—C8	117.3 (3)
O3—Zn1—N2	100.90 (9)	C4—C9—C8	121.0 (3)
O5—Zn1—O2	171.45 (8)	N2—C10—C11	121.9 (3)
O1—Zn1—O2	76.48 (8)	N2—C10—H10	119.1
O3—Zn1—O2	79.00 (8)	C11—C10—H10	119.1
N2—Zn1—O2	75.65 (9)	C12—C11—C10	120.0 (3)
O1—Zn2—O3ⁱ	174.06 (8)	C12—C11—H11	120.0
O1—Zn2—N3ⁱ	106.56 (9)	C10—C11—H11	120.0
O3ⁱ—Zn2—N3ⁱ	79.38 (9)	C11—C12—C13	120.0 (3)
O1—Zn2—N1	79.00 (9)	C11—C12—H12	120.0
O3ⁱ—Zn2—N1	100.41 (9)	C13—C12—H12	120.0
N3ⁱ—Zn2—N1	97.67 (10)	C14—C13—C12	124.1 (3)
O1—Zn2—O2	78.13 (8)	C14—C13—C18	119.3 (3)
O3ⁱ—Zn2—O2	101.96 (8)	C12—C13—C18	116.6 (3)
N3ⁱ—Zn2—O2	92.21 (9)	C15—C14—C13	119.5 (3)
N1—Zn2—O2	156.85 (9)	C15—C14—H14	120.2
O1—Zn2—O2ⁱ	94.12 (8)	C13—C14—H14	120.2
O3ⁱ—Zn2—O2ⁱ	80.07 (8)	C14—C15—C16	121.4 (3)
N3ⁱ—Zn2—O2ⁱ	156.41 (9)	C14—C15—H15	119.3
N1—Zn2—O2ⁱ	97.33 (8)	C16—C15—H15	119.3
O2—Zn2—O2ⁱ	80.84 (8)	C17—C16—C15	121.1 (3)
C8—O1—Zn1	137.0 (2)	C17—C16—H16	119.5
C8—O1—Zn2	114.79 (19)	C15—C16—H16	119.5
Zn1—O1—Zn2	108.21 (9)	O2—C17—C16	124.7 (3)
C17—O2—Zn2	130.34 (18)	O2—C17—C18	117.0 (3)
C17—O2—Zn2ⁱ	116.92 (17)	C16—C17—C18	118.3 (3)
Zn2—O2—Zn2ⁱ	99.16 (8)	N2—C18—C13	122.0 (3)
C17—O2—Zn1	111.59 (18)	N2—C18—C17	117.6 (3)
Zn2—O2—Zn1	97.19 (8)	C13—C18—C17	120.3 (3)
Zn2ⁱ—O2—Zn1	94.70 (8)	N3—C19—C20	122.0 (3)
C26—O3—Zn1	132.98 (19)	N3—C19—H19	119.0
C26—O3—Zn2ⁱ	113.58 (18)	C20—C19—H19	119.0
Zn1—O3—Zn2ⁱ	105.54 (9)	C21—C20—C19	120.3 (3)
C28—O5—Zn1	105.6 (2)	C21—C20—H20	119.9
H1W1—O1W—H1W2	110.6	C19—C20—H20	119.9
H1W3—O1W'—H1W4	108.9	C20—C21—C22	119.6 (3)
C1—N1—C9	119.7 (3)	C20—C21—H21	120.2
C1—N1—Zn2	128.3 (2)	C22—C21—H21	120.2
C9—N1—Zn2	111.9 (2)	C23—C22—C27	119.2 (3)
C10—N2—C18	119.5 (3)	C23—C22—C21	124.3 (3)
C10—N2—Zn1	123.8 (2)	C27—C22—C21	116.6 (3)
C18—N2—Zn1	116.6 (2)	C24—C23—C22	119.6 (3)
C19—N3—C27	119.0 (3)	C24—C23—H23	120.2
C19—N3—Zn2ⁱ	128.9 (2)	C22—C23—H23	120.2
C27—N3—Zn2ⁱ	111.93 (19)	C23—C24—C25	121.7 (3)
N1—C1—C2	122.3 (3)	C23—C24—H24	119.1
N1—C1—H1A	118.8	C25—C24—H24	119.1
C2—C1—H1A	118.8	C26—C25—C24	120.8 (3)
C3—C2—C1	118.8 (3)	C26—C25—H25	119.6
C3—C2—H2A	120.6	C24—C25—H25	119.6
C1—C2—H2A	120.6	O3—C26—C25	124.5 (3)
C2—C3—C4	120.6 (3)	O3—C26—C27	117.3 (3)
C2—C3—H3	119.7	C25—C26—C27	118.2 (3)
C4—C3—H3	119.7	N3—C27—C22	122.4 (3)
C5—C4—C9	118.9 (3)	N3—C27—C26	117.1 (3)
C5—C4—C3	124.3 (3)	C22—C27—C26	120.5 (3)
C9—C4—C3	116.8 (3)	O4—C28—O5	122.9 (3)
C6—C5—C4	119.7 (3)	O4—C28—C29	121.1 (3)
C6—C5—H5	120.2	O5—C28—C29	116.0 (3)
C4—C5—H5	120.2	C28—C29—H29A	109.5
C5—C6—C7	121.6 (3)	C28—C29—H29B	109.5
C5—C6—H6	119.2	H29A—C29—H29B	109.5
C7—C6—H6	119.2	C28—C29—H29C	109.5
C8—C7—C6	121.1 (3)	H29A—C29—H29C	109.5
C8—C7—H7	119.4	H29B—C29—H29C	109.5
C6—C7—H7	119.4

O5—Zn1—O1—C8	−10.2 (3)	Zn1—O1—C8—C7	2.4 (5)
O3—Zn1—O1—C8	103.1 (3)	Zn2—O1—C8—C7	−179.7 (3)
N2—Zn1—O1—C8	−133.2 (3)	Zn1—O1—C8—C9	−177.0 (2)
O2—Zn1—O1—C8	178.2 (3)	Zn2—O1—C8—C9	0.9 (3)
O5—Zn1—O1—Zn2	171.85 (9)	C6—C7—C8—O1	178.4 (3)
O3—Zn1—O1—Zn2	−74.88 (11)	C6—C7—C8—C9	−2.2 (5)
N2—Zn1—O1—Zn2	48.84 (17)	C1—N1—C9—C4	−0.2 (4)
O2—Zn1—O1—Zn2	0.27 (9)	Zn2—N1—C9—C4	176.6 (2)
N3ⁱ—Zn2—O1—C8	92.5 (2)	C1—N1—C9—C8	179.1 (3)
N1—Zn2—O1—C8	−2.3 (2)	Zn2—N1—C9—C8	−4.1 (3)
O2—Zn2—O1—C8	−178.7 (2)	C5—C4—C9—N1	179.0 (3)
O2ⁱ—Zn2—O1—C8	−99.0 (2)	C3—C4—C9—N1	0.0 (4)
N3ⁱ—Zn2—O1—Zn1	−89.06 (11)	C5—C4—C9—C8	−0.3 (5)
N1—Zn2—O1—Zn1	176.12 (12)	C3—C4—C9—C8	−179.3 (3)
O2—Zn2—O1—Zn1	−0.29 (9)	O1—C8—C9—N1	2.3 (4)
O2ⁱ—Zn2—O1—Zn1	79.45 (10)	C7—C8—C9—N1	−177.2 (3)
O1—Zn2—O2—C17	−126.2 (2)	O1—C8—C9—C4	−178.4 (3)
O3ⁱ—Zn2—O2—C17	59.9 (2)	C7—C8—C9—C4	2.1 (5)
N3ⁱ—Zn2—O2—C17	−19.7 (2)	C18—N2—C10—C11	1.9 (5)
N1—Zn2—O2—C17	−135.2 (3)	Zn1—N2—C10—C11	−173.0 (2)
O2ⁱ—Zn2—O2—C17	137.6 (3)	N2—C10—C11—C12	0.9 (5)
O1—Zn2—O2—Zn2ⁱ	96.21 (9)	C10—C11—C12—C13	−2.1 (5)
O3ⁱ—Zn2—O2—Zn2ⁱ	−77.72 (9)	C11—C12—C13—C14	−179.3 (3)
N3ⁱ—Zn2—O2—Zn2ⁱ	−157.33 (10)	C11—C12—C13—C18	0.7 (4)
N1—Zn2—O2—Zn2ⁱ	87.2 (2)	C12—C13—C14—C15	178.4 (3)
O2ⁱ—Zn2—O2—Zn2ⁱ	0.0	C18—C13—C14—C15	−1.7 (5)
O1—Zn2—O2—Zn1	0.24 (8)	C13—C14—C15—C16	0.0 (5)
O3ⁱ—Zn2—O2—Zn1	−173.69 (7)	C14—C15—C16—C17	1.5 (5)
N3ⁱ—Zn2—O2—Zn1	106.71 (9)	Zn2—O2—C17—C16	−50.7 (4)
N1—Zn2—O2—Zn1	−8.7 (2)	Zn2ⁱ—O2—C17—C16	81.0 (3)
O2ⁱ—Zn2—O2—Zn1	−95.97 (9)	Zn1—O2—C17—C16	−171.5 (2)
O1—Zn1—O2—C17	138.47 (19)	Zn2—O2—C17—C18	131.3 (2)
O3—Zn1—O2—C17	−115.28 (19)	Zn2ⁱ—O2—C17—C18	−96.9 (3)
N2—Zn1—O2—C17	−10.89 (18)	Zn1—O2—C17—C18	10.5 (3)
O1—Zn1—O2—Zn2	−0.25 (8)	C15—C16—C17—O2	−179.2 (3)
O3—Zn1—O2—Zn2	105.99 (9)	C15—C16—C17—C18	−1.2 (4)
N2—Zn1—O2—Zn2	−149.61 (10)	C10—N2—C18—C13	−3.4 (4)
O1—Zn1—O2—Zn2ⁱ	−100.12 (9)	Zn1—N2—C18—C13	171.9 (2)
O3—Zn1—O2—Zn2ⁱ	6.13 (8)	C10—N2—C18—C17	176.8 (3)
N2—Zn1—O2—Zn2ⁱ	110.52 (9)	Zn1—N2—C18—C17	−7.9 (3)
O5—Zn1—O3—C26	32.8 (3)	C14—C13—C18—N2	−177.9 (3)
O1—Zn1—O3—C26	−79.1 (3)	C12—C13—C18—N2	2.1 (4)
N2—Zn1—O3—C26	134.8 (3)	C14—C13—C18—C17	1.9 (4)
O2—Zn1—O3—C26	−152.3 (3)	C12—C13—C18—C17	−178.2 (3)
O5—Zn1—O3—Zn2ⁱ	178.57 (9)	O2—C17—C18—N2	−2.5 (4)
O1—Zn1—O3—Zn2ⁱ	66.64 (11)	C16—C17—C18—N2	179.4 (3)
N2—Zn1—O3—Zn2ⁱ	−79.45 (11)	O2—C17—C18—C13	177.7 (3)
O2—Zn1—O3—Zn2ⁱ	−6.58 (8)	C16—C17—C18—C13	−0.4 (4)
O1—Zn1—O5—C28	−72.3 (2)	C27—N3—C19—C20	−0.5 (5)
O3—Zn1—O5—C28	178.01 (19)	Zn2ⁱ—N3—C19—C20	−175.8 (2)
N2—Zn1—O5—C28	73.8 (2)	N3—C19—C20—C21	3.0 (5)
O1—Zn2—N1—C1	179.9 (3)	C19—C20—C21—C22	−2.1 (5)
O3ⁱ—Zn2—N1—C1	−6.2 (3)	C20—C21—C22—C23	177.8 (3)
N3ⁱ—Zn2—N1—C1	74.4 (3)	C20—C21—C22—C27	−0.9 (5)
O2—Zn2—N1—C1	−171.2 (2)	C27—C22—C23—C24	−1.5 (6)
O2ⁱ—Zn2—N1—C1	−87.4 (3)	C21—C22—C23—C24	179.8 (4)
O1—Zn2—N1—C9	3.41 (19)	C22—C23—C24—C25	0.3 (7)
O3ⁱ—Zn2—N1—C9	177.39 (19)	C23—C24—C25—C26	0.4 (6)
N3ⁱ—Zn2—N1—C9	−102.1 (2)	Zn1—O3—C26—C25	−27.0 (5)
O2—Zn2—N1—C9	12.4 (3)	Zn2ⁱ—O3—C26—C25	−170.7 (3)
O2ⁱ—Zn2—N1—C9	96.2 (2)	Zn1—O3—C26—C27	152.3 (2)
O5—Zn1—N2—C10	10.5 (3)	Zn2ⁱ—O3—C26—C27	8.6 (3)
O1—Zn1—N2—C10	136.1 (2)	C24—C25—C26—O3	179.3 (3)
O3—Zn1—N2—C10	−99.5 (2)	C24—C25—C26—C27	0.0 (5)
O2—Zn1—N2—C10	−175.1 (3)	C19—N3—C27—C22	−2.7 (4)
O5—Zn1—N2—C18	−164.5 (2)	Zn2ⁱ—N3—C27—C22	173.4 (2)
O1—Zn1—N2—C18	−38.9 (3)	C19—N3—C27—C26	179.9 (3)
O3—Zn1—N2—C18	85.4 (2)	Zn2ⁱ—N3—C27—C26	−4.0 (3)
O2—Zn1—N2—C18	9.9 (2)	C23—C22—C27—N3	−175.4 (3)
C9—N1—C1—C2	0.0 (5)	C21—C22—C27—N3	3.4 (5)
Zn2—N1—C1—C2	−176.2 (2)	C23—C22—C27—C26	1.9 (5)
N1—C1—C2—C3	0.3 (5)	C21—C22—C27—C26	−179.3 (3)
C1—C2—C3—C4	−0.5 (5)	O3—C26—C27—N3	−3.1 (4)
C2—C3—C4—C5	−178.6 (3)	C25—C26—C27—N3	176.3 (3)
C2—C3—C4—C9	0.3 (5)	O3—C26—C27—C22	179.5 (3)
C9—C4—C5—C6	−1.5 (5)	C25—C26—C27—C22	−1.2 (5)
C3—C4—C5—C6	177.4 (3)	Zn1—O5—C28—O4	0.2 (4)
C4—C5—C6—C7	1.5 (6)	Zn1—O5—C28—C29	−179.0 (2)
C5—C6—C7—C8	0.4 (6)

Symmetry code: (i) −x+2, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1w—H1w1···O4	0.84	2.04	2.858 (6)	166
O1w'—H1w3···O4	0.84	2.04	2.83 (2)	157

Experimental details

Crystal data
Chemical formula	[Zn₄(C₉H₆NO)₆(C₂H₃O₂)₂]·2H₂O
M_r	1280.49
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	11.3313 (3), 11.8367 (3), 13.5379 (3)
α, β, γ (°)	111.070 (2), 107.740 (2), 112.579 (2)
V (Å³)	1342.16 (6)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	1.84
Crystal size (mm)	0.15 × 0.10 × 0.05

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.657, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	12632, 6146, 4418
R_int	0.037
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.102, 1.00
No. of reflections	6146
No. of parameters	372
No. of restraints	12
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.63, −0.44

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1w—H1w1···O4	0.84	2.04	2.858 (6)	166
O1w'—H1w3···O4	0.84	2.04	2.83 (2)	157

Acknowledgements

We thank Shahid Beheshti University and the University of Malaya for supporting this study.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
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Sattarzadeh, E., Mohammadnezhad, G., Amini, M. M. & Ng, S. W. (2009b). Acta Cryst. E65, m554. Web of Science CSD CrossRef IUCr Journals 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
Westrip, S. P. (2009). publCIF. In preparation. Google Scholar

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