catena-Poly[[[aqua­(2,2′-bipyridine-κ2N,N′)zinc]-μ-furan-2,5-dicarboxyl­ato-κ2O2:O5] dihydrate]

Li, Y.-F.; Xu, Y.; Qin, X.-L.; Yuan, Y.-P.; Gao, W.-Y.

doi:10.1107/S1600536812045503

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 12| December 2012| Page m1466

doi:10.1107/S1600536812045503

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catena-Poly[[[aqua(2,2′-bipyridine-κ²N,N′)zinc]-μ-furan-2,5-dicarboxylato-κ²O²:O⁵] dihydrate]

Ya-Feng Li,^a ^* Yue Xu,^a Xiao-Lin Qin,^a Yong-Peng Yuan ^a and Wen-Yuan Gao ^a

^aSchool of Chemical Engineering, Changchun University of Technology, Changchun 130012, People's Republic of China
^*Correspondence e-mail: fly012345@sohu.com

(Received 31 October 2012; accepted 3 November 2012; online 10 November 2012)

In the title hydrated coordination polymer, {[Zn(C₆H₂O₅)(C₁₀H₈N₂)(H₂O)]·2H₂O}_n, an infinite [1-10] chain is formed by the linking of [Zn(C₁₀H₈N₂)(H₂O)]²⁺ entities by bridging, monodentate furan-2,5-dicarboxylate dianionic linkers. The Zn²⁺ coordination geometry is a trigonal bipyramid, with one N atom (from 2,2′-bipyridine) and one O atom (from the bridging dianion) in the axial positions. For each Zn^II atom, the dihedral angle between the furan ring of its coordinated bridging ligand and its coordinated bipyridine ring system is 87.19 (8)°. O—H⋯O hydrogen bonds involving both the coordinated and uncoordinated water molecules generate a layer motif parallel to (001).

Related literature

For a related structure, see: Li, et al. (2012 ).

Experimental

Crystal data

[Zn(C₆H₂O₅)(C₁₀H₈N₂)(H₂O)]·2H₂O
M_r = 429.70
Triclinic, $[P \overline 1]$
a = 8.5815 (17) Å
b = 9.2928 (19) Å
c = 12.753 (3) Å
α = 69.99 (3)°
β = 87.63 (3)°
γ = 65.85 (3)°
V = 866.2 (3) Å³
Z = 2
Mo Kα radiation
μ = 1.47 mm⁻¹
T = 293 K
0.43 × 0.34 × 0.23 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.57, T_max = 0.73
8557 measured reflections
3925 independent reflections
3433 reflections with I > 2σ(I)
R_int = 0.023

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.102
S = 1.10
3925 reflections
262 parameters
9 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.67 e Å⁻³
Δρ_min = −0.59 e Å⁻³

Table 1
Selected bond lengths (Å)

Zn1—O4ⁱ	2.0180 (17)
Zn1—O1	2.0221 (17)
Zn1—N2	2.078 (2)
Zn1—O1W	2.1142 (17)
Zn1—N1	2.1298 (19)
Symmetry code: (i) x+1, y-1, z.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1A⋯O5ⁱⁱ	0.87 (2)	1.89 (2)	2.724 (2)	159 (2)
O1W—H1B⋯O1ⁱⁱⁱ	0.86 (2)	1.88 (2)	2.701 (3)	158 (2)
O2W—H2A⋯O2	0.89 (2)	1.91 (3)	2.731 (4)	152 (5)
O2W—H2B⋯O5^iv	0.89 (2)	2.12 (3)	2.902 (4)	146 (5)
O3W—H3A⋯O4	0.88 (2)	2.27 (3)	3.050 (4)	148 (4)
O3W—H3B⋯O2W	0.87 (2)	2.15 (3)	2.943 (7)	152 (5)
Symmetry codes: (ii) -x+1, -y+1, -z+1; (iii) -x+2, -y, -z+1; (iv) x+1, y, z.

Data collection: PROCESS-AUTO (Rigaku, 1998 ); cell refinement: PROCESS-AUTO; data reduction: Crystal Structure (Rigaku/MSC, 2002 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2000 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812045503/hb6980sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812045503/hb6980Isup2.hkl

checkCIF report

Comment top

As the analogous structure of BDC (benzene-1,4-dicarboxyl acid), FDA (furan-2,5-dicarboxyl acid) attracts attentions owing to the bond angle of two carboxyl groups about 126° Recently, we utilized furan-2,5-dicarboxyl acid as the ligand to construct coordination polymers (Li, et al., 2012). As an extension of this work, a chainlike compound, [Zn(H₂O)(C₁₀H₈N₂)(C₆H₂O₅)]^.2H₂O (I), is now determined.

The asymmetric unit of (I) is consisted of one Zn(II) cation, one furan-2,5-dicarboxylate anion, one 2,2'-bipyridine and three waters involving in one coordinated waters and two structural water (Fig.1). Zn cation is coordinated by two N atoms of 2,2'-bipyridine, one water O atoms and two carboxylate O atoms, exhibiting a triangle bipyramid geometry (Table 1) with one O atoms of furan-2,5-dicarboxylate and one nitrogen atom of 2,2'-bipyridine in the axial positions. The adjacent Zn cations are connected by the furan-2,5-dicarboxylate to infinite chain (Fig.2). O_water—H···O hydrogen bonds (Table 2) help to consolidate the structure.

Related literature top

For a related structure, see: Li, et al. (2012).

Experimental top

In a typically synthesized route of (I), furan-2,5-dicarboxyl acid (0.0156 g, 0.10 mmol), Zn(NO₃)₂^.6H₂O (0.0300 g, 0.10 mmol), and 2,2'-bipyridine (0.0156, 0.10 mmol) and NaOH (0.004, 0.10 mmol) were dissolved in water (5 ml, 278 mmol) under stirring. The mixture with molar ratio of 1 (furan-2,5-dicarboxyl acid): 1 (Zn(NO₃)₂^.6H₂O): 1 (2,2'-bipyridine): 1 NaOH: 2780 H₂O was layed under room temperature for 5 days. The colorless block product was collected as a single phase.

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO (Rigaku, 1998); data reduction: Crystal Structure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2000); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The unit cell of (I), showing displacement ellipsoids at the 50% probability level. [Symmetry code: (i) 1 + x, -1 + y, z.]
	Fig. 2. The polyhedral plot of (I), displaying the infinite chain formed by linking the adjacent Zn cations with furan-2,5-dicarboxylate.
	Fig. 3. The ball-stick packing diagram of (I). The adjacent chains are holded together by the O_water–H···O H-bonding interactions to the supermolecular net.

catena-Poly[[[aqua(2,2'-bipyridine-κ²N,N')zinc]-µ- furan-2,5-dicarboxylato-κ²O²:O⁵] dihydrate] top

Crystal data top

[Zn(C₆H₂O₅)(C₁₀H₈N₂)(H₂O)]·2H₂O	Z = 2
M_r = 429.70	F(000) = 440
Triclinic, P1	D_x = 1.648 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.5815 (17) Å	Cell parameters from 2000 reflections
b = 9.2928 (19) Å	θ = 3.3–27.5°
c = 12.753 (3) Å	µ = 1.47 mm⁻¹
α = 69.99 (3)°	T = 293 K
β = 87.63 (3)°	Block, colorless
γ = 65.85 (3)°	0.43 × 0.34 × 0.23 mm
V = 866.2 (3) Å³

Data collection top

Rigaku R-AXIS RAPID diffractometer	3925 independent reflections
Radiation source: fine-focus sealed tube	3433 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
Detector resolution: 10.00 pixels mm^-1	θ_max = 27.5°, θ_min = 3.3°
ω scans	h = −10→11
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −11→12
T_min = 0.57, T_max = 0.73	l = −16→16
8557 measured reflections

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) = 0.102	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	w = 1/[σ²(F_o²) + (0.0684P)²] where P = (F_o² + 2F_c²)/3
3925 reflections	(Δ/σ)_max < 0.001
262 parameters	Δρ_max = 0.67 e Å⁻³
9 restraints	Δρ_min = −0.59 e Å⁻³

Crystal data top

[Zn(C₆H₂O₅)(C₁₀H₈N₂)(H₂O)]·2H₂O	γ = 65.85 (3)°
M_r = 429.70	V = 866.2 (3) Å³
Triclinic, P1	Z = 2
a = 8.5815 (17) Å	Mo Kα radiation
b = 9.2928 (19) Å	µ = 1.47 mm⁻¹
c = 12.753 (3) Å	T = 293 K
α = 69.99 (3)°	0.43 × 0.34 × 0.23 mm
β = 87.63 (3)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	3925 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	3433 reflections with I > 2σ(I)
T_min = 0.57, T_max = 0.73	R_int = 0.023
8557 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	9 restraints
wR(F²) = 0.102	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	Δρ_max = 0.67 e Å⁻³
3925 reflections	Δρ_min = −0.59 e Å⁻³
262 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.

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	1.02440 (3)	0.08858 (3)	0.301753 (18)	0.03278 (11)
O1	0.8000 (2)	0.15494 (19)	0.36940 (13)	0.0406 (3)
O2	0.7541 (3)	0.4185 (2)	0.26829 (18)	0.0583 (5)
O3	0.44358 (18)	0.53732 (17)	0.35155 (12)	0.0331 (3)
O4	0.1984 (2)	0.84783 (19)	0.33670 (14)	0.0437 (4)
O5	0.0295 (2)	0.7310 (2)	0.43028 (18)	0.0558 (5)
N1	0.9017 (2)	0.1152 (2)	0.15016 (15)	0.0381 (4)
N2	1.1346 (2)	0.2204 (2)	0.18046 (15)	0.0366 (4)
C1	0.7097 (3)	0.3148 (3)	0.33458 (17)	0.0351 (4)
C2	0.5420 (3)	0.3677 (2)	0.38022 (17)	0.0308 (4)
C3	0.4610 (3)	0.2801 (3)	0.4468 (2)	0.0401 (5)
H3	0.5014	0.1632	0.4773	0.048*
C4	0.3028 (3)	0.3994 (3)	0.4615 (2)	0.0427 (5)
H4	0.2189	0.3765	0.5034	0.051*
C5	0.2977 (3)	0.5523 (3)	0.40305 (17)	0.0329 (4)
C6	0.1649 (3)	0.7242 (3)	0.38908 (18)	0.0355 (4)
C7	0.7801 (3)	0.0635 (3)	0.1426 (2)	0.0494 (6)
H7	0.7456	0.0075	0.2082	0.059*
C8	0.7031 (4)	0.0910 (4)	0.0391 (3)	0.0573 (7)
H8	0.6182	0.0545	0.0354	0.069*
C9	0.7551 (4)	0.1728 (4)	−0.0565 (2)	0.0593 (7)
H9	0.7053	0.1926	−0.1263	0.071*
C10	0.8824 (4)	0.2266 (3)	−0.0497 (2)	0.0492 (6)
H10	0.9190	0.2821	−0.1143	0.059*
C11	0.9536 (3)	0.1952 (3)	0.05628 (18)	0.0387 (5)
C12	1.0886 (3)	0.2478 (3)	0.07396 (18)	0.0373 (4)
C13	1.1640 (3)	0.3239 (3)	−0.0142 (2)	0.0491 (6)
H13	1.1321	0.3414	−0.0878	0.059*
C14	1.2854 (4)	0.3726 (3)	0.0090 (2)	0.0558 (6)
H14	1.3368	0.4232	−0.0489	0.067*
C15	1.3307 (4)	0.3460 (3)	0.1186 (2)	0.0524 (6)
H15	1.4113	0.3799	0.1359	0.063*
C16	1.2541 (3)	0.2686 (3)	0.2017 (2)	0.0465 (5)
H16	1.2862	0.2485	0.2759	0.056*
O1W	1.1508 (2)	0.1017 (2)	0.43471 (13)	0.0397 (3)
H1A	1.079 (3)	0.175 (3)	0.462 (2)	0.048*
H1B	1.189 (3)	0.005 (2)	0.4890 (18)	0.048*
O2W	0.8859 (7)	0.6378 (6)	0.2753 (2)	0.1299 (15)
H2A	0.872 (8)	0.543 (5)	0.291 (4)	0.156*
H2B	0.919 (8)	0.632 (7)	0.342 (3)	0.156*
O3W	0.5178 (5)	0.8678 (5)	0.2312 (3)	0.1173 (12)
H3A	0.456 (5)	0.842 (6)	0.285 (3)	0.141*
H3B	0.612 (4)	0.777 (5)	0.240 (4)	0.141*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.03146 (16)	0.02874 (14)	0.03086 (15)	−0.00672 (10)	0.00895 (10)	−0.01011 (10)
O1	0.0337 (8)	0.0338 (7)	0.0378 (8)	−0.0014 (6)	0.0106 (6)	−0.0102 (7)
O2	0.0560 (11)	0.0468 (9)	0.0676 (12)	−0.0222 (9)	0.0314 (10)	−0.0170 (9)
O3	0.0296 (7)	0.0248 (6)	0.0381 (7)	−0.0058 (6)	0.0078 (6)	−0.0109 (6)
O4	0.0395 (9)	0.0297 (7)	0.0515 (9)	−0.0041 (6)	0.0042 (7)	−0.0152 (7)
O5	0.0394 (10)	0.0562 (10)	0.0831 (13)	−0.0156 (8)	0.0249 (9)	−0.0454 (11)
N1	0.0325 (9)	0.0392 (9)	0.0380 (9)	−0.0089 (8)	0.0072 (7)	−0.0165 (8)
N2	0.0384 (10)	0.0324 (8)	0.0339 (9)	−0.0114 (7)	0.0099 (7)	−0.0108 (8)
C1	0.0311 (10)	0.0355 (10)	0.0346 (10)	−0.0092 (9)	0.0064 (8)	−0.0140 (9)
C2	0.0286 (10)	0.0249 (8)	0.0335 (9)	−0.0053 (7)	0.0036 (8)	−0.0116 (8)
C3	0.0385 (12)	0.0266 (9)	0.0505 (12)	−0.0106 (9)	0.0113 (10)	−0.0128 (9)
C4	0.0360 (12)	0.0384 (11)	0.0554 (13)	−0.0154 (9)	0.0186 (10)	−0.0205 (11)
C5	0.0284 (10)	0.0323 (9)	0.0373 (10)	−0.0083 (8)	0.0072 (8)	−0.0175 (9)
C6	0.0317 (11)	0.0335 (10)	0.0404 (11)	−0.0052 (8)	0.0028 (8)	−0.0225 (9)
C7	0.0407 (13)	0.0544 (14)	0.0549 (14)	−0.0168 (11)	0.0118 (11)	−0.0263 (13)
C8	0.0395 (14)	0.0617 (16)	0.0741 (18)	−0.0131 (12)	0.0014 (12)	−0.0378 (16)
C9	0.0544 (17)	0.0597 (16)	0.0537 (15)	−0.0058 (13)	−0.0076 (13)	−0.0294 (14)
C10	0.0542 (15)	0.0433 (12)	0.0390 (12)	−0.0084 (11)	0.0010 (10)	−0.0162 (11)
C11	0.0384 (12)	0.0325 (10)	0.0347 (10)	−0.0039 (9)	0.0059 (9)	−0.0133 (9)
C12	0.0389 (12)	0.0288 (9)	0.0334 (10)	−0.0051 (8)	0.0083 (8)	−0.0102 (8)
C13	0.0528 (15)	0.0445 (12)	0.0349 (11)	−0.0125 (11)	0.0143 (10)	−0.0073 (10)
C14	0.0545 (16)	0.0459 (13)	0.0536 (15)	−0.0193 (12)	0.0230 (12)	−0.0062 (12)
C15	0.0469 (15)	0.0481 (13)	0.0614 (16)	−0.0234 (12)	0.0133 (12)	−0.0152 (13)
C16	0.0487 (14)	0.0474 (12)	0.0450 (12)	−0.0217 (11)	0.0098 (10)	−0.0168 (11)
O1W	0.0422 (9)	0.0358 (7)	0.0343 (8)	−0.0091 (7)	0.0081 (6)	−0.0140 (7)
O2W	0.221 (4)	0.178 (4)	0.0612 (16)	−0.155 (4)	0.025 (2)	−0.038 (2)
O3W	0.091 (2)	0.135 (3)	0.123 (3)	−0.069 (2)	0.019 (2)	−0.017 (2)

Geometric parameters (Å, º) top

Zn1—O4ⁱ	2.0180 (17)	C7—H7	0.9300
Zn1—O1	2.0221 (17)	C8—C9	1.364 (5)
Zn1—N2	2.078 (2)	C8—H8	0.9300
Zn1—O1W	2.1142 (17)	C9—C10	1.391 (4)
Zn1—N1	2.1298 (19)	C9—H9	0.9300
O1—C1	1.281 (3)	C10—C11	1.392 (3)
O2—C1	1.226 (3)	C10—H10	0.9300
O3—C5	1.367 (2)	C11—C12	1.481 (3)
O3—C2	1.369 (2)	C12—C13	1.397 (3)
O4—C6	1.255 (3)	C13—C14	1.371 (4)
O5—C6	1.242 (3)	C13—H13	0.9300
N1—C7	1.334 (3)	C14—C15	1.378 (4)
N1—C11	1.342 (3)	C14—H14	0.9300
N2—C12	1.338 (3)	C15—C16	1.371 (4)
N2—C16	1.344 (3)	C15—H15	0.9300
C1—C2	1.483 (3)	C16—H16	0.9300
C2—C3	1.345 (3)	O1W—H1A	0.873 (16)
C3—C4	1.413 (3)	O1W—H1B	0.864 (16)
C3—H3	0.9300	O2W—H2A	0.890 (19)
C4—C5	1.343 (3)	O2W—H2B	0.890 (19)
C4—H4	0.9300	O3W—H3A	0.879 (19)
C5—C6	1.488 (3)	O3W—H3B	0.871 (19)
C7—C8	1.395 (4)

O4ⁱ—Zn1—O1	123.96 (7)	O5—C6—C5	116.0 (2)
O4ⁱ—Zn1—N2	101.59 (8)	O4—C6—C5	117.87 (19)
O1—Zn1—N2	134.31 (7)	O4—C6—C5	117.87 (19)
O4ⁱ—Zn1—O1W	89.61 (7)	N1—C7—C8	121.8 (3)
O1—Zn1—O1W	91.03 (7)	N1—C7—H7	119.1
N2—Zn1—O1W	92.77 (7)	C8—C7—H7	119.1
O4ⁱ—Zn1—N1	96.59 (8)	C9—C8—C7	118.5 (3)
O1—Zn1—N1	92.21 (7)	C9—C8—H8	120.7
N2—Zn1—N1	78.06 (8)	C7—C8—H8	120.7
O1W—Zn1—N1	169.79 (7)	C8—C9—C10	120.1 (2)
C1—O1—Zn1	112.97 (14)	C8—C9—H9	119.9
C5—O3—C2	105.96 (16)	C10—C9—H9	119.9
C6—O4—Zn1ⁱⁱ	122.19 (15)	C9—C10—C11	118.3 (3)
C7—N1—C11	119.8 (2)	C9—C10—H10	120.8
C7—N1—Zn1	125.87 (17)	C11—C10—H10	120.8
C11—N1—Zn1	114.32 (15)	N1—C11—C10	121.3 (2)
C12—N2—C16	119.0 (2)	N1—C11—C12	115.47 (19)
C12—N2—Zn1	115.74 (15)	C10—C11—C12	123.2 (2)
C16—N2—Zn1	125.13 (16)	N2—C12—C13	120.9 (2)
O2—C1—O1	124.2 (2)	N2—C12—C11	116.2 (2)
O2—C1—O1	124.2 (2)	C13—C12—C11	122.9 (2)
O2—C1—C2	121.42 (19)	C14—C13—C12	119.4 (2)
O2—C1—C2	121.42 (19)	C14—C13—H13	120.3
O1—C1—C2	114.39 (19)	C12—C13—H13	120.3
C3—C2—O3	110.11 (18)	C13—C14—C15	119.4 (2)
C3—C2—C1	132.51 (18)	C13—C14—H14	120.3
O3—C2—C1	117.38 (18)	C15—C14—H14	120.3
C2—C3—C4	106.94 (19)	C16—C15—C14	118.5 (2)
C2—C3—H3	126.5	C16—C15—H15	120.7
C4—C3—H3	126.5	C14—C15—H15	120.7
C5—C4—C3	106.4 (2)	N2—C16—C15	122.8 (2)
C5—C4—H4	126.8	N2—C16—H16	118.6
C3—C4—H4	126.8	C15—C16—H16	118.6
C4—C5—O3	110.58 (18)	Zn1—O1W—H1A	110.7 (18)
C4—C5—C6	130.7 (2)	Zn1—O1W—H1B	109.3 (17)
O3—C5—C6	118.72 (18)	H1A—O1W—H1B	106 (2)
O5—C6—O4	126.2 (2)	H2A—O2W—H2B	103 (3)
O5—C6—O4	126.2 (2)	H3A—O3W—H3B	108 (3)

O4ⁱ—Zn1—O1—C1	−179.73 (13)	C2—O3—C5—C4	−0.2 (2)
N2—Zn1—O1—C1	−4.84 (19)	C2—O3—C5—C6	178.97 (17)
O1W—Zn1—O1—C1	90.05 (15)	O4—O4—C6—O5	0.00 (18)
N1—Zn1—O1—C1	−80.27 (15)	Zn1ⁱⁱ—O4—C6—O5	−3.8 (3)
O4ⁱ—Zn1—N1—C7	82.2 (2)	O4—O4—C6—C5	0.00 (19)
O1—Zn1—N1—C7	−42.31 (19)	Zn1ⁱⁱ—O4—C6—C5	175.53 (13)
N2—Zn1—N1—C7	−177.3 (2)	C4—C5—C6—O5	−6.4 (3)
O1W—Zn1—N1—C7	−150.7 (3)	O3—C5—C6—O5	174.61 (18)
O4ⁱ—Zn1—N1—C11	−99.23 (15)	C4—C5—C6—O4	174.2 (2)
O1—Zn1—N1—C11	136.22 (15)	O3—C5—C6—O4	−4.8 (3)
N2—Zn1—N1—C11	1.27 (14)	C4—C5—C6—O4	174.2 (2)
O1W—Zn1—N1—C11	27.8 (4)	O3—C5—C6—O4	−4.8 (3)
O4ⁱ—Zn1—N2—C12	90.59 (16)	C11—N1—C7—C8	−0.4 (4)
O1—Zn1—N2—C12	−85.08 (17)	Zn1—N1—C7—C8	178.01 (18)
O1W—Zn1—N2—C12	−179.24 (15)	N1—C7—C8—C9	0.2 (4)
N1—Zn1—N2—C12	−3.79 (14)	C7—C8—C9—C10	0.1 (4)
O4ⁱ—Zn1—N2—C16	−84.86 (19)	C8—C9—C10—C11	−0.2 (4)
O1—Zn1—N2—C16	99.5 (2)	C7—N1—C11—C10	0.3 (3)
O1W—Zn1—N2—C16	5.32 (19)	Zn1—N1—C11—C10	−178.29 (17)
N1—Zn1—N2—C16	−179.24 (19)	C7—N1—C11—C12	179.80 (19)
O2—O2—C1—O1	0.00 (12)	Zn1—N1—C11—C12	1.2 (2)
O2—O2—C1—C2	0.00 (9)	C9—C10—C11—N1	0.0 (3)
Zn1—O1—C1—O2	−0.9 (3)	C9—C10—C11—C12	−179.4 (2)
Zn1—O1—C1—O2	−0.9 (3)	C16—N2—C12—C13	0.5 (3)
Zn1—O1—C1—C2	178.44 (13)	Zn1—N2—C12—C13	−175.20 (16)
C5—O3—C2—C3	0.1 (2)	C16—N2—C12—C11	−178.66 (19)
C5—O3—C2—C1	179.71 (16)	Zn1—N2—C12—C11	5.6 (2)
O2—C1—C2—C3	175.1 (2)	N1—C11—C12—N2	−4.5 (3)
O2—C1—C2—C3	175.1 (2)	C10—C11—C12—N2	175.0 (2)
O1—C1—C2—C3	−4.2 (3)	N1—C11—C12—C13	176.33 (19)
O2—C1—C2—O3	−4.4 (3)	C10—C11—C12—C13	−4.2 (3)
O2—C1—C2—O3	−4.4 (3)	N2—C12—C13—C14	−0.7 (3)
O1—C1—C2—O3	176.30 (17)	C11—C12—C13—C14	178.5 (2)
O3—C2—C3—C4	0.0 (3)	C12—C13—C14—C15	−0.1 (4)
C1—C2—C3—C4	−179.5 (2)	C13—C14—C15—C16	1.1 (4)
C2—C3—C4—C5	−0.1 (3)	C12—N2—C16—C15	0.5 (4)
C3—C4—C5—O3	0.2 (3)	Zn1—N2—C16—C15	175.76 (19)
C3—C4—C5—C6	−178.8 (2)	C14—C15—C16—N2	−1.3 (4)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1A···O5ⁱⁱⁱ	0.87 (2)	1.89 (2)	2.724 (2)	159 (2)
O1W—H1B···O1^iv	0.86 (2)	1.88 (2)	2.701 (3)	158 (2)
O2W—H2A···O2	0.89 (2)	1.91 (3)	2.731 (4)	152 (5)
O2W—H2B···O5^v	0.89 (2)	2.12 (3)	2.902 (4)	146 (5)
O3W—H3A···O4	0.88 (2)	2.27 (3)	3.050 (4)	148 (4)
O3W—H3B···O2W	0.87 (2)	2.15 (3)	2.943 (7)	152 (5)

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

Experimental details

Crystal data
Chemical formula	[Zn(C₆H₂O₅)(C₁₀H₈N₂)(H₂O)]·2H₂O
M_r	429.70
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	8.5815 (17), 9.2928 (19), 12.753 (3)
α, β, γ (°)	69.99 (3), 87.63 (3), 65.85 (3)
V (Å³)	866.2 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.47
Crystal size (mm)	0.43 × 0.34 × 0.23

Data collection
Diffractometer	Rigaku R-AXIS RAPID diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.57, 0.73
No. of measured, independent and observed [I > 2σ(I)] reflections	8557, 3925, 3433
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.102, 1.10
No. of reflections	3925
No. of parameters	262
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)	0.67, −0.59

Computer programs: PROCESS-AUTO (Rigaku, 1998), Crystal Structure (Rigaku/MSC, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 2000).

Selected bond lengths (Å) top

Zn1—O4ⁱ	2.0180 (17)	Zn1—O1W	2.1142 (17)
Zn1—O1	2.0221 (17)	Zn1—N1	2.1298 (19)
Zn1—N2	2.078 (2)

Symmetry code: (i) x+1, y−1, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1A···O5ⁱⁱ	0.873 (16)	1.891 (19)	2.724 (2)	159 (2)
O1W—H1B···O1ⁱⁱⁱ	0.864 (16)	1.88 (2)	2.701 (3)	158 (2)
O2W—H2A···O2	0.890 (19)	1.91 (3)	2.731 (4)	152 (5)
O2W—H2B···O5^iv	0.890 (19)	2.12 (3)	2.902 (4)	146 (5)
O3W—H3A···O4	0.879 (19)	2.27 (3)	3.050 (4)	148 (4)
O3W—H3B···O2W	0.871 (19)	2.15 (3)	2.943 (7)	152 (5)

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

Acknowledgements

This project was sponsored by the Scientific Research Foundation for the Returned Overseas Team, Chinese Education Ministry.

References

Brandenburg, K. (2000). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan. Google Scholar
Li, Y.-F., Xu, Y., Qin, X.-L., Gao, W.-Y. & Gao, Y. (2012). Acta Cryst. E68, m659. CSD CrossRef IUCr Journals Google Scholar
Rigaku (1998). PROCESS-AUTO. Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku/MSC (2002). CrystalStructure. Rigaku/MSC Inc., The Woodlands, Texas, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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