catena-Poly[[[(2,2′-bipyridyl-κ2N,N′)zinc(II)]-μ3-(5-hydroxy­isophthalato-κ4O,O′:O′′:O′′′)] monohydrate]

Li, X.-F.; An, Y.; Yin, Y.-S.

doi:10.1107/S1600536807059880

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catena-Poly[[[(2,2′-bipyridyl-κ²N,N′)zinc(II)]-μ₃-(5-hydroxyisophthalato-κ⁴O,O′:O′′:O′′′)] monohydrate]

X.-F. Li, Y. An and Y.-S. Yin

The title compound, {[Zn(C₈H₄O₅)(C₁₀H₈N₂)]·H₂O}_n, was synthesized by reacting Zn(NO₃)₂, 5-hydroxyisophthalic acid and 2,2′-bipyridine under hydrothermal conditions. Self-assembly between the bridging ligands, chelating ligands and metal ions results in a one-dimensional coordination polymer, in which the Zn^II atom is six-coordinate and shows a [ZnN₂O₄] octahedral geometry. The ribbons are interconnected by an extensive network of hydrogen bonds involving the water molecule, the hydroxyl group and the carboxylate O atoms, forming a two-dimensional layer. These layers are connected through π–π interactions between the pyridyl rings [centroid-to-centroid distance 3.57 (1) Å].

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807059880/hy2097sup1.cif Contains datablock I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807059880/hy2097Isup2.hkl Contains datablock I

CCDC reference: 672730

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.005 Å
R factor = 0.038
wR factor = 0.111
Data-to-parameter ratio = 15.5

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT232_ALERT_2_B Hirshfeld Test Diff (M-X)  Zn1    -   O2      ..      12.44 su

Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.98
PLAT128_ALERT_4_C Non-standard setting of Space-group P2/c    ....      P2/n
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.51 Ratio
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Zn1    -   O1      ..       9.45 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Zn1    -   O3_b    ..       5.62 su
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O2
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          2

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          3

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   8 ALERT level C = Check and explain
   3 ALERT level G = General alerts; check

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   5 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

The design and construction of coordination polymers has attracted much attention owing to their intriguing topologies and potential applications as functional materials (Inoue et al., 2001). Many networks with various structural motifs have been documented in the past decade (Amabilino & Stoddart, 1995). Unlike pyridine-2,4-, 3,4- 2,5- and 2,6-dicarboxylic acids, which have been widely used as bridging ligands to assemble various coordination polymers, 5-hydroxyisophthalic acid (H₂hip) as a member of the multicarboxylate ligands has been rarely reported (Plater et al., 2001). We report here the synthesis and structure of a zinc(II) coordination polymer constructed from 5-hydroxyisophthalic acid and 2,2'-bipyridine (bpy).

In the title compound, the asymmetric unit contains one Zn^II atom, one hip ligand, one bpy ligand and one lattice water molecule. Each Zn^II atom is coordinated by four O atoms from three hip ligands (Table 1) and two N atoms from a chelating bpy ligand in a distorted octahedral geometry (Fig. 1). Each pair of adjacent Zn^II atoms are bridged by two hip ligands to form a binuclear Zn subunit. The adjacent binuclear subunits are further interconnected by two hip ligands to form a one-dimensional ribbon running along the a + c direction (Fig. 2). These ribbons are decorated with bpy ligands alternately at two sides.

The ribbons are interconnected by an extensive network of hydrogen bonds involving water molecule, hydroxyl group and carboxylate O atoms (Table 2), forming a two-dimensional layer. The layers are connected through π–π interactions between the pyridyl rings with a centroid-to-centroid distance of 3.57 (1) Å.

Related literature top

For related literature, see: Amabilino & Stoddart (1995); Inoue et al. (2001); Plater et al. (2001).

Experimental top

A mixture of Zn(NO₃)₂.2H₂O (0.120 g, 0.5 mmol), 5-hydroxyisophthalic acid (0.091 g, 0.5 mmol), 2,2'-bipyridine (0.078 g, 0.5 mmol), NaOH (0.04 g, 1 mmol) and water (10 ml) was sealed in a 23 ml Teflon-lined reactor, which was heated at 453 K for 6 d and then cooled to room temperature at a rate of 5 K h^-1 (yield 58%). Analysis calculated for C₁₈H₁₄N₂O₆Zn: C 51.51, H 3.36, N 6.67%; found: C 51.68, H 3.64, N 6.73%.

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, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2001); software used to prepare material for publication: SHELXTL (Bruker, 2001).

Figures top

	Fig. 1. Part of the polymeric structure of the title compound with symmetric equivalent atoms to complete the Zn coordination. Displacement ellipsoids are drawn at the 30% probability level. Lattice water molecule has been omitted. [Symmetry codes: (i) x + 1/2, -y + 2, z + 1/2; (ii) -x, -y + 2, -z.]
	Fig. 2. A view of the one-dimensional ribbon structure. H atoms and lattice water molecule have been omitted for clarity.

catena-Poly[[(2,2'-bipyridyl-κ²N,N')zinc(II)]-µ₃– (5-hydroxyisophthalato-κ⁴O,O':O'':O''') monohydrate] top

Crystal data top

[Zn(C₈H₄O₅)(C₁₀H₈N₂)]·H₂O	F(000) = 856
M_r = 419.68	D_x = 1.656 Mg m⁻³
Monoclinic, P2/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yac	Cell parameters from 3685 reflections
a = 8.777 (2) Å	θ = 2.5–22.4°
b = 10.9763 (16) Å	µ = 1.50 mm⁻¹
c = 17.981 (3) Å	T = 293 K
β = 103.650 (14)°	Block, colourless
V = 1683.4 (5) Å³	0.37 × 0.32 × 0.23 mm
Z = 4

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	3880 independent reflections
Radiation source: fine-focus sealed tube	2902 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
ϕ and ω scans	θ_max = 27.5°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→1
T_min = 0.608, T_max = 0.720	k = −1→14
5111 measured reflections	l = −23→23

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.111	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.0632P)²] where P = (F_o² + 2F_c²)/3
3880 reflections	(Δ/σ)_max = 0.001
250 parameters	Δρ_max = 0.43 e Å⁻³
3 restraints	Δρ_min = −0.72 e Å⁻³

Crystal data top

[Zn(C₈H₄O₅)(C₁₀H₈N₂)]·H₂O	V = 1683.4 (5) Å³
M_r = 419.68	Z = 4
Monoclinic, P2/n	Mo Kα radiation
a = 8.777 (2) Å	µ = 1.50 mm⁻¹
b = 10.9763 (16) Å	T = 293 K
c = 17.981 (3) Å	0.37 × 0.32 × 0.23 mm
β = 103.650 (14)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	3880 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2902 reflections with I > 2σ(I)
T_min = 0.608, T_max = 0.720	R_int = 0.027
5111 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	3 restraints
wR(F²) = 0.111	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.43 e Å⁻³
3880 reflections	Δρ_min = −0.72 e Å⁻³
250 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
Zn1	0.04335 (4)	0.79387 (3)	0.171663 (16)	0.02547 (12)
C1	−0.1934 (4)	0.8493 (3)	0.06332 (15)	0.0333 (7)
C2	−0.3194 (3)	0.8800 (3)	−0.00631 (14)	0.0266 (6)
C3	−0.2932 (3)	0.9639 (3)	−0.06037 (14)	0.0265 (6)
H3A	−0.1974	1.0041	−0.0529	0.032*
C4	−0.4116 (3)	0.9871 (2)	−0.12579 (14)	0.0252 (6)
C5	−0.5553 (3)	0.9282 (3)	−0.13638 (15)	0.0294 (6)
H5A	−0.6339	0.9437	−0.1800	0.035*
C6	−0.5818 (3)	0.8457 (3)	−0.08168 (16)	0.0290 (6)
C7	−0.4635 (4)	0.8226 (3)	−0.01715 (15)	0.0297 (6)
H7A	−0.4811	0.7678	0.0194	0.036*
C8	−0.3810 (3)	1.0759 (3)	−0.18412 (14)	0.0260 (6)
C9	−0.0538 (4)	0.6455 (3)	0.29853 (17)	0.0422 (8)
H9A	−0.0723	0.7214	0.3176	0.051*
C10	−0.0911 (5)	0.5421 (4)	0.33393 (19)	0.0558 (10)
H10A	−0.1345	0.5484	0.3762	0.067*
C11	−0.0640 (5)	0.4309 (4)	0.3066 (2)	0.0634 (12)
H11A	−0.0877	0.3604	0.3303	0.076*
C12	−0.0003 (5)	0.4235 (3)	0.2430 (2)	0.0509 (9)
H12A	0.0187	0.3482	0.2232	0.061*
C13	0.1464 (4)	0.4292 (3)	0.1073 (2)	0.0473 (8)
H13A	0.1391	0.3524	0.1280	0.057*
C14	0.2047 (4)	0.4431 (4)	0.0426 (2)	0.0546 (10)
H14A	0.2353	0.3751	0.0188	0.066*
C15	0.2171 (4)	0.5564 (4)	0.0140 (2)	0.0510 (9)
H15A	0.2572	0.5670	−0.0290	0.061*
C16	0.1694 (4)	0.6549 (3)	0.04976 (17)	0.0393 (7)
H16A	0.1782	0.7325	0.0303	0.047*
C17	0.0992 (3)	0.5322 (3)	0.14052 (17)	0.0320 (6)
C18	0.0340 (4)	0.5299 (3)	0.20978 (17)	0.0333 (7)
N1	0.0082 (3)	0.6396 (2)	0.23741 (13)	0.0313 (5)
N2	0.1105 (3)	0.6432 (2)	0.11174 (13)	0.0297 (5)
O1	−0.0610 (3)	0.9002 (2)	0.07345 (12)	0.0420 (5)
O2	−0.2190 (3)	0.7718 (2)	0.10882 (12)	0.0491 (6)
O3	−0.2652 (2)	1.1432 (2)	−0.16680 (11)	0.0359 (5)
O4	−0.4802 (2)	1.07902 (19)	−0.24867 (10)	0.0329 (5)
O5	−0.7167 (3)	0.7825 (2)	−0.08941 (13)	0.0432 (6)
H5B	−0.7905	0.8242	−0.1123	0.065*
O1W	0.9935 (4)	0.1276 (2)	0.15885 (16)	0.0578 (7)
H1WA	1.003 (6)	0.086 (3)	0.1992 (13)	0.087*
H1WB	1.014 (6)	0.085 (3)	0.1235 (15)	0.087*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.03291 (19)	0.02413 (18)	0.01813 (16)	0.00019 (14)	0.00356 (12)	−0.00048 (12)
C1	0.0404 (17)	0.0369 (16)	0.0210 (12)	0.0125 (14)	0.0042 (12)	−0.0026 (12)
C2	0.0306 (14)	0.0297 (14)	0.0193 (11)	0.0034 (12)	0.0058 (10)	−0.0008 (11)
C3	0.0263 (13)	0.0314 (14)	0.0206 (11)	−0.0006 (12)	0.0027 (10)	−0.0018 (11)
C4	0.0296 (14)	0.0262 (13)	0.0195 (11)	−0.0015 (12)	0.0053 (10)	0.0002 (10)
C5	0.0307 (14)	0.0337 (15)	0.0216 (12)	0.0005 (13)	0.0018 (11)	0.0021 (11)
C6	0.0276 (14)	0.0304 (15)	0.0292 (13)	−0.0018 (12)	0.0071 (11)	0.0015 (12)
C7	0.0371 (16)	0.0284 (14)	0.0246 (12)	0.0024 (13)	0.0090 (12)	0.0044 (11)
C8	0.0298 (14)	0.0274 (14)	0.0209 (12)	−0.0011 (12)	0.0066 (11)	0.0001 (10)
C9	0.0488 (19)	0.050 (2)	0.0289 (14)	−0.0088 (17)	0.0105 (14)	−0.0011 (14)
C10	0.064 (2)	0.071 (3)	0.0339 (17)	−0.015 (2)	0.0151 (17)	0.0118 (18)
C11	0.077 (3)	0.054 (2)	0.060 (2)	−0.018 (2)	0.019 (2)	0.023 (2)
C12	0.060 (2)	0.0345 (18)	0.056 (2)	−0.0060 (17)	0.0090 (18)	0.0107 (16)
C13	0.054 (2)	0.0302 (16)	0.055 (2)	0.0049 (16)	0.0071 (17)	−0.0062 (15)
C14	0.053 (2)	0.052 (2)	0.061 (2)	0.0072 (19)	0.0178 (19)	−0.0225 (19)
C15	0.051 (2)	0.063 (2)	0.0433 (19)	−0.0040 (19)	0.0198 (17)	−0.0173 (18)
C16	0.0465 (19)	0.0411 (18)	0.0344 (15)	−0.0047 (16)	0.0175 (14)	−0.0064 (14)
C17	0.0290 (15)	0.0302 (15)	0.0338 (15)	−0.0015 (13)	0.0014 (12)	−0.0023 (12)
C18	0.0325 (15)	0.0300 (15)	0.0336 (15)	−0.0038 (13)	0.0002 (12)	0.0010 (12)
N1	0.0349 (13)	0.0339 (13)	0.0235 (11)	−0.0032 (11)	0.0038 (10)	0.0042 (10)
N2	0.0314 (13)	0.0285 (12)	0.0296 (12)	−0.0034 (11)	0.0083 (10)	−0.0056 (10)
O1	0.0365 (12)	0.0500 (14)	0.0333 (11)	0.0009 (11)	−0.0044 (9)	0.0020 (10)
O2	0.0505 (15)	0.0616 (16)	0.0317 (11)	0.0056 (13)	0.0029 (10)	0.0201 (11)
O3	0.0363 (11)	0.0440 (12)	0.0266 (10)	−0.0162 (10)	0.0062 (9)	0.0010 (9)
O4	0.0380 (11)	0.0356 (11)	0.0211 (9)	−0.0060 (9)	−0.0009 (8)	0.0071 (8)
O5	0.0322 (12)	0.0487 (14)	0.0468 (13)	−0.0086 (11)	0.0057 (10)	0.0143 (11)
O1W	0.0690 (18)	0.0398 (14)	0.0631 (17)	0.0135 (14)	0.0125 (15)	0.0079 (13)

Geometric parameters (Å, º) top

Zn1—O4ⁱ	2.0449 (19)	C9—H9A	0.9300
Zn1—O3ⁱⁱ	2.087 (2)	C10—C11	1.357 (6)
Zn1—N1	2.129 (2)	C10—H10A	0.9300
Zn1—N2	2.131 (2)	C11—C12	1.390 (6)
Zn1—O1	2.135 (2)	C11—H11A	0.9300
Zn1—O2	2.326 (3)	C12—C18	1.377 (4)
C1—O2	1.237 (4)	C12—H12A	0.9300
C1—O1	1.263 (4)	C13—C17	1.387 (4)
C1—C2	1.500 (4)	C13—C14	1.386 (5)
C2—C7	1.385 (4)	C13—H13A	0.9300
C2—C3	1.397 (4)	C14—C15	1.360 (6)
C3—C4	1.397 (4)	C14—H14A	0.9300
C3—H3A	0.9300	C15—C16	1.373 (5)
C4—C5	1.390 (4)	C15—H15A	0.9300
C4—C8	1.502 (4)	C16—N2	1.341 (4)
C5—C6	1.396 (4)	C16—H16A	0.9300
C5—H5A	0.9300	C17—N2	1.337 (4)
C6—O5	1.351 (4)	C17—C18	1.489 (4)
C6—C7	1.386 (4)	C18—N1	1.342 (4)
C7—H7A	0.9300	O3—Zn1ⁱⁱ	2.087 (2)
C8—O3	1.235 (3)	O4—Zn1ⁱⁱⁱ	2.0449 (19)
C8—O4	1.277 (3)	O5—H5B	0.8200
C9—N1	1.338 (4)	O1W—H1WA	0.85 (3)
C9—C10	1.378 (5)	O1W—H1WB	0.85 (3)

O4ⁱ—Zn1—O3ⁱⁱ	93.05 (8)	O3—C8—O4	123.9 (3)
O4ⁱ—Zn1—N1	95.83 (9)	O3—C8—C4	118.9 (2)
O3ⁱⁱ—Zn1—N1	123.06 (9)	O4—C8—C4	117.2 (2)
O4ⁱ—Zn1—N2	165.77 (8)	N1—C9—C10	121.7 (3)
O3ⁱⁱ—Zn1—N2	82.17 (9)	N1—C9—H9A	119.1
N1—Zn1—N2	75.95 (10)	C10—C9—H9A	119.1
O4ⁱ—Zn1—O1	96.42 (9)	C11—C10—C9	119.5 (3)
O3ⁱⁱ—Zn1—O1	90.39 (9)	C11—C10—H10A	120.2
N1—Zn1—O1	143.52 (9)	C9—C10—H10A	120.2
N2—Zn1—O1	97.00 (9)	C10—C11—C12	119.3 (3)
O4ⁱ—Zn1—O2	99.15 (9)	C10—C11—H11A	120.4
O3ⁱⁱ—Zn1—O2	147.19 (8)	C12—C11—H11A	120.4
N1—Zn1—O2	86.00 (9)	C18—C12—C11	118.6 (4)
N2—Zn1—O2	91.94 (9)	C18—C12—H12A	120.7
O1—Zn1—O2	58.17 (8)	C11—C12—H12A	120.7
O4ⁱ—Zn1—C1	99.93 (9)	C17—C13—C14	118.6 (3)
O3ⁱⁱ—Zn1—C1	119.10 (9)	C17—C13—H13A	120.7
N1—Zn1—C1	114.40 (10)	C14—C13—H13A	120.7
N2—Zn1—C1	94.09 (9)	C15—C14—C13	119.7 (3)
O1—Zn1—C1	29.40 (9)	C15—C14—H14A	120.1
O2—Zn1—C1	28.80 (9)	C13—C14—H14A	120.1
O2—C1—O1	120.9 (3)	C14—C15—C16	118.9 (3)
O2—C1—C2	119.5 (3)	C14—C15—H15A	120.5
O1—C1—C2	119.6 (3)	C16—C15—H15A	120.5
O2—C1—Zn1	64.87 (17)	N2—C16—C15	122.2 (3)
O1—C1—Zn1	56.11 (15)	N2—C16—H16A	118.9
C2—C1—Zn1	173.3 (2)	C15—C16—H16A	118.9
C7—C2—C3	119.8 (2)	N2—C17—C13	121.3 (3)
C7—C2—C1	119.0 (3)	N2—C17—C18	114.7 (3)
C3—C2—C1	121.2 (3)	C13—C17—C18	124.0 (3)
C4—C3—C2	119.6 (3)	N1—C18—C12	121.8 (3)
C4—C3—H3A	120.2	N1—C18—C17	115.2 (3)
C2—C3—H3A	120.2	C12—C18—C17	123.0 (3)
C5—C4—C3	120.1 (2)	C9—N1—C18	119.0 (3)
C5—C4—C8	120.8 (2)	C9—N1—Zn1	123.9 (2)
C3—C4—C8	119.1 (2)	C18—N1—Zn1	116.67 (19)
C4—C5—C6	120.1 (2)	C17—N2—C16	119.2 (3)
C4—C5—H5A	119.9	C17—N2—Zn1	117.20 (19)
C6—C5—H5A	119.9	C16—N2—Zn1	123.5 (2)
O5—C6—C7	117.2 (3)	C1—O1—Zn1	94.49 (18)
O5—C6—C5	123.3 (3)	C1—O2—Zn1	86.3 (2)
C7—C6—C5	119.5 (3)	C8—O3—Zn1ⁱⁱ	155.2 (2)
C2—C7—C6	120.9 (3)	C8—O4—Zn1ⁱⁱⁱ	119.67 (18)
C2—C7—H7A	119.5	C6—O5—H5B	109.5
C6—C7—H7A	119.5	H1WA—O1W—H1WB	111 (3)

O4ⁱ—Zn1—C1—O2	−90.96 (19)	C17—C18—N1—Zn1	5.8 (3)
O3ⁱⁱ—Zn1—C1—O2	169.88 (17)	O4ⁱ—Zn1—N1—C9	16.1 (3)
N1—Zn1—C1—O2	10.2 (2)	O3ⁱⁱ—Zn1—N1—C9	113.6 (2)
N2—Zn1—C1—O2	86.58 (19)	N2—Zn1—N1—C9	−175.7 (3)
O1—Zn1—C1—O2	−176.4 (3)	O1—Zn1—N1—C9	−93.0 (3)
O4ⁱ—Zn1—C1—O1	85.45 (18)	O2—Zn1—N1—C9	−82.7 (3)
O3ⁱⁱ—Zn1—C1—O1	−13.7 (2)	C1—Zn1—N1—C9	−87.6 (3)
N1—Zn1—C1—O1	−173.44 (17)	O4ⁱ—Zn1—N1—C18	−171.7 (2)
N2—Zn1—C1—O1	−97.02 (18)	O3ⁱⁱ—Zn1—N1—C18	−74.2 (2)
O2—Zn1—C1—O1	176.4 (3)	N2—Zn1—N1—C18	−3.5 (2)
O2—C1—C2—C7	1.5 (4)	O1—Zn1—N1—C18	79.2 (3)
O1—C1—C2—C7	179.3 (3)	O2—Zn1—N1—C18	89.5 (2)
O2—C1—C2—C3	−177.8 (3)	C1—Zn1—N1—C18	84.6 (2)
O1—C1—C2—C3	0.1 (4)	C13—C17—N2—C16	−0.4 (4)
C7—C2—C3—C4	−1.4 (4)	C18—C17—N2—C16	179.3 (3)
C1—C2—C3—C4	177.8 (2)	C13—C17—N2—Zn1	−177.3 (2)
C2—C3—C4—C5	0.9 (4)	C18—C17—N2—Zn1	2.4 (3)
C2—C3—C4—C8	−179.0 (2)	C15—C16—N2—C17	0.8 (5)
C3—C4—C5—C6	0.0 (4)	C15—C16—N2—Zn1	177.5 (3)
C8—C4—C5—C6	179.9 (3)	O4ⁱ—Zn1—N2—C17	56.3 (5)
C4—C5—C6—O5	−177.8 (3)	O3ⁱⁱ—Zn1—N2—C17	127.4 (2)
C4—C5—C6—C7	−0.4 (4)	N1—Zn1—N2—C17	0.4 (2)
C3—C2—C7—C6	1.0 (4)	O1—Zn1—N2—C17	−143.2 (2)
C1—C2—C7—C6	−178.3 (3)	O2—Zn1—N2—C17	−85.0 (2)
O5—C6—C7—C2	177.5 (3)	C1—Zn1—N2—C17	−113.8 (2)
C5—C6—C7—C2	−0.1 (4)	O4ⁱ—Zn1—N2—C16	−120.5 (4)
C5—C4—C8—O3	166.5 (3)	O3ⁱⁱ—Zn1—N2—C16	−49.4 (2)
C3—C4—C8—O3	−13.6 (4)	N1—Zn1—N2—C16	−176.4 (3)
C5—C4—C8—O4	−11.8 (4)	O1—Zn1—N2—C16	40.1 (3)
C3—C4—C8—O4	168.1 (3)	O2—Zn1—N2—C16	98.2 (2)
N1—C9—C10—C11	0.3 (6)	C1—Zn1—N2—C16	69.5 (3)
C9—C10—C11—C12	−0.6 (6)	O2—C1—O1—Zn1	3.8 (3)
C10—C11—C12—C18	0.3 (6)	C2—C1—O1—Zn1	−174.0 (2)
C17—C13—C14—C15	1.2 (6)	O4ⁱ—Zn1—O1—C1	−98.84 (18)
C13—C14—C15—C16	−0.8 (6)	O3ⁱⁱ—Zn1—O1—C1	168.04 (18)
C14—C15—C16—N2	−0.2 (6)	N1—Zn1—O1—C1	10.1 (3)
C14—C13—C17—N2	−0.6 (5)	N2—Zn1—O1—C1	85.89 (18)
C14—C13—C17—C18	179.7 (3)	O2—Zn1—O1—C1	−2.04 (17)
C11—C12—C18—N1	0.3 (5)	O1—C1—O2—Zn1	−3.5 (3)
C11—C12—C18—C17	−178.7 (3)	C2—C1—O2—Zn1	174.3 (2)
N2—C17—C18—N1	−5.4 (4)	O4ⁱ—Zn1—O2—C1	93.99 (18)
C13—C17—C18—N1	174.3 (3)	O3ⁱⁱ—Zn1—O2—C1	−16.5 (3)
N2—C17—C18—C12	173.6 (3)	N1—Zn1—O2—C1	−170.74 (19)
C13—C17—C18—C12	−6.7 (5)	N2—Zn1—O2—C1	−94.97 (19)
C10—C9—N1—C18	0.3 (5)	O1—Zn1—O2—C1	2.08 (17)
C10—C9—N1—Zn1	172.4 (3)	O4—C8—O3—Zn1ⁱⁱ	−71.6 (6)
C12—C18—N1—C9	−0.6 (5)	C4—C8—O3—Zn1ⁱⁱ	110.2 (4)
C17—C18—N1—C9	178.4 (3)	O3—C8—O4—Zn1ⁱⁱⁱ	−2.8 (4)
C12—C18—N1—Zn1	−173.2 (3)	C4—C8—O4—Zn1ⁱⁱⁱ	175.39 (17)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5B···O1W^iv	0.82	1.86	2.646 (4)	161
O1W—H1WA···O4^v	0.85 (3)	2.02 (2)	2.790 (3)	150 (4)
O1W—H1WB···O1^vi	0.85 (3)	2.25 (3)	2.910 (4)	135 (4)

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

Experimental details

Crystal data
Chemical formula	[Zn(C₈H₄O₅)(C₁₀H₈N₂)]·H₂O
M_r	419.68
Crystal system, space group	Monoclinic, P2/n
Temperature (K)	293
a, b, c (Å)	8.777 (2), 10.9763 (16), 17.981 (3)
β (°)	103.650 (14)
V (Å³)	1683.4 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.50
Crystal size (mm)	0.37 × 0.32 × 0.23

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.608, 0.720
No. of measured, independent and observed [I > 2σ(I)] reflections	5111, 3880, 2902
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.111, 1.02
No. of reflections	3880
No. of parameters	250
No. of restraints	3
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.43, −0.72

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2001).

Selected geometric parameters (Å, º) top

Zn1—O4ⁱ	2.0449 (19)	Zn1—N2	2.131 (2)
Zn1—O3ⁱⁱ	2.087 (2)	Zn1—O1	2.135 (2)
Zn1—N1	2.129 (2)	Zn1—O2	2.326 (3)

O4ⁱ—Zn1—O3ⁱⁱ	93.05 (8)	N1—Zn1—O1	143.52 (9)
O4ⁱ—Zn1—N1	95.83 (9)	N2—Zn1—O1	97.00 (9)
O3ⁱⁱ—Zn1—N1	123.06 (9)	O4ⁱ—Zn1—O2	99.15 (9)
O4ⁱ—Zn1—N2	165.77 (8)	O3ⁱⁱ—Zn1—O2	147.19 (8)
O3ⁱⁱ—Zn1—N2	82.17 (9)	N1—Zn1—O2	86.00 (9)
N1—Zn1—N2	75.95 (10)	N2—Zn1—O2	91.94 (9)
O4ⁱ—Zn1—O1	96.42 (9)	O1—Zn1—O2	58.17 (8)
O3ⁱⁱ—Zn1—O1	90.39 (9)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5B···O1Wⁱⁱⁱ	0.82	1.86	2.646 (4)	160.9
O1W—H1WA···O4^iv	0.85 (3)	2.02 (2)	2.790 (3)	150 (4)
O1W—H1WB···O1^v	0.85 (3)	2.25 (3)	2.910 (4)	135 (4)

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

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