catena-Poly[[[aqua­(pyrazino­[2,3-f][1,10]phenanthroline-κ2N8,N9)zinc(II)]-μ-penta­nedioato] monohydrate]

Fang, W.

doi:10.1107/S1600536810042340

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 12| December 2010| Pages m1522-m1523

https://doi.org/10.1107/S1600536810042340

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catena-Poly[[[aqua(pyrazino[2,3-f][1,10]phenanthroline-κ²N⁸,N⁹)zinc(II)]-μ-pentanedioato] monohydrate]

Wei Fang ^a ^*

^aDepartment of Chemistry, Baicheng Normal University, Baicheng 137000, People's Republic of China
^*Correspondence e-mail: fangwei1026@126.com

(Received 23 September 2010; accepted 19 October 2010; online 6 November 2010)

In the title compound, {[Zn(C₅H₆O₄)(C₁₄H₈N₄)(H₂O)]·H₂O}_n, the Zn²⁺ ion is coordinated by an N,N′-bidentate pyrazino[2,3-f][1,10]phenanthroline (pyphen) ligand, a water molecule and a monodentate glutarate (glu) dianion. A symmetry-generated O:O′-bidentate glu dianion completes a distorted cis-ZnN₂O₄ octahedral coordination geometry for the metal ion. The bridging glu species generates [110] polymeric chains in the crystal. O—H⋯O hydrogen bonds involving both the coordinated and uncoordinated water molecules help to consolidate the structure and neighbouring pyphen units interact through numerous aromatic π–π interactions [minimum centroid–centroid separation = 3.654 (3) Å], resulting in a two-dimensional network.

Related literature

For the synthesis of the ligand, see: Dickeson & Summers (1970 ). For related structures, see: Fang-Wei & Mei (2007 ); Li et al. (2006 ).

Experimental

Crystal data

[Zn(C₅H₆O₄)(C₁₄H₈N₄)(H₂O)]·H₂O
M_r = 463.74
Triclinic, $[P \overline 1]$
a = 6.397 (3) Å
b = 9.384 (5) Å
c = 16.409 (8) Å
α = 98.067 (5)°
β = 100.859 (5)°
γ = 101.274 (5)°
V = 932.5 (8) Å³
Z = 2
Mo Kα radiation
μ = 1.37 mm⁻¹
T = 292 K
0.78 × 0.52 × 0.36 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2002 ) T_min = 0.432, T_max = 0.611
8019 measured reflections
3702 independent reflections
2929 reflections with I > 2σ(I)
R_int = 0.062

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.100
S = 0.98
3702 reflections
283 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.86 e Å⁻³
Δρ_min = −0.59 e Å⁻³

Table 1
Selected bond lengths (Å)

Zn1—O2	1.987 (2)
Zn1—N1	2.120 (3)
Zn1—O5	2.137 (2)
Zn1—O4ⁱ	2.154 (2)
Zn1—N2	2.188 (2)
Zn1—O3ⁱ	2.347 (2)
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
O5—H5A⋯OW1ⁱⁱ	0.82	1.89	2.702 (3)	173
O5—H5B⋯O4ⁱⁱⁱ	1.00 (4)	1.91 (4)	2.856 (3)	157 (3)
OW1—HWA1⋯O4^iv	0.85 (4)	2.03 (4)	2.840 (4)	161 (3)
OW1—HWBA⋯O2	0.79 (4)	1.95 (4)	2.733 (4)	170 (4)
Symmetry codes: (ii) -x+1, -y, -z+1; (iii) -x+2, -y+1, -z+1; (iv) -x+3, -y+1, -z+1.

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); 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 global, I. DOI: https://doi.org/10.1107/S1600536810042340/hb5645sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810042340/hb5645Isup2.hkl

checkCIF report

Comment top

The 1,10-phenanthroline (phen) ligand and its derivatives are important ligands with numerous uses in the construction of metal-organic complexes.Supramolecular architectures baswd on the phen derivative pyrazino[2,3-f][1,10]phenanthroline(PyPhen) molecule have considerably less attention (Li et al.,2006) A s part of our ongoing studies in this area (Fang-Wei & Mei, 2007). We selected glutaric acid (C₅H₆O₄^2-) to act as a metal-metal linker in its deprotonated form and L as a secondary ligand, generating the title compound, [Zn(C₁₄H₈N₄)(C₅H₆O₄)(H₂O).H₂O], a new coordinationg polymer, which is reported here. In compound (I), the Zn^II atom of unit is surrounded by two N atoms derived from the bidentate PyPhen ligand, three O atoms from two glutaric acid dianions (one monodentate, one bidentate) and one water molecule (Figure 1, Table 1) a distorted octahedral cis-ZnN₂O₄arrangement is formed. Neighboring Zn^II atoms are bridged by the centrosymmetric glutaric acid ligands forming a one-dimensional chain structure (Fig.2). In the crystal structure, adjacent chains are connected through π-π interactions between PyPhen and PyPhen ligands with a minimum centroid -centroid stacking distance of 3.372 Å. O—H···O hydrogen bonds involving the water molecules and carboxylate O atom acceptors (Table 2) complete the structure.

Related literature top

For the synthesis of the ligand, see: Dickeson & Summers (1970). For related structures, see: Fang-Wei & Mei (2007); Li et al. (2006).

Experimental top

The pyphen ligand was synthesized according to the literature method of Dickeson & Summers (1970). A mixture of ZnCl₂ (0.3 mmol), pyphen (0.1 mmol) and glutaric acid (0.3 mmol) in distilled water (30 ml) was stirred thoroughly for 1 h at ambient temperature. The pH was adjusted to 7.5 with aqueous NaOH solution. The suspension was then sealed in a Teflon-lined stainless steel reaction vessel (40 ml). The reaction was performed under autogeneous pressure and static conditions in an oven at 443 K for 4.5 d. The vessel was then cooled slowly inside the oven to 298 K at a rate of 5 K h^-1 before opening: amaranth (red) blocks of (I) were collected.

Structure description top

For the synthesis of the ligand, see: Dickeson & Summers (1970). For related structures, see: Fang-Wei & Mei (2007); Li et al. (2006).

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); 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. view of the local coordination of Zn(II) with displacement ellipsoids drawn at the 30% probability level.
	Fig. 2. A view of the two-dimensional supramolecular structure of (I) generated by π-π interactions and hydrogen-bonding.

catena-Poly[[[aqua(pyrazino[2,3-f][1,10]phenanthroline- κ²N⁸,N⁹)zinc(II)]-µ-pentanedioato] monohydrate] top

Crystal data top

[Zn(C₅H₆O₄)(C₁₄H₈N₄)(H₂O)]·H₂O	V = 932.5 (8) Å³
M_r = 463.74	Z = 2
Triclinic, P1	F(000) = 476
Hall symbol: -P 1	D_x = 1.652 Mg m⁻³
a = 6.397 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.384 (5) Å	θ = 2.0–26.3°
c = 16.409 (8) Å	µ = 1.37 mm⁻¹
α = 98.067 (5)°	T = 292 K
β = 100.859 (5)°	Block, amaranth
γ = 101.274 (5)°	0.78 × 0.52 × 0.36 mm

Data collection top

Bruker SMART CCD diffractometer	3702 independent reflections
Radiation source: fine-focus sealed tube	2929 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.062
Detector resolution: 0 pixels mm^-1	θ_max = 26.1°, θ_min = 2.3°
ω scans	h = −7→7
Absorption correction: multi-scan (SADABS; Bruker, 2002)	k = −11→11
T_min = 0.432, T_max = 0.611	l = −20→20
8019 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)] = 0.040	Hydrogen site location: constr
wR(F²) = 0.100	H atoms treated by a mixture of independent and constrained refinement
S = 0.98	w = 1/[σ²(F_o²) + (0.0464P)²] where P = (F_o² + 2F_c²)/3
3702 reflections	(Δ/σ)_max = 0.001
283 parameters	Δρ_max = 0.86 e Å⁻³
0 restraints	Δρ_min = −0.59 e Å⁻³

Crystal data top

[Zn(C₅H₆O₄)(C₁₄H₈N₄)(H₂O)]·H₂O	γ = 101.274 (5)°
M_r = 463.74	V = 932.5 (8) Å³
Triclinic, P1	Z = 2
a = 6.397 (3) Å	Mo Kα radiation
b = 9.384 (5) Å	µ = 1.37 mm⁻¹
c = 16.409 (8) Å	T = 292 K
α = 98.067 (5)°	0.78 × 0.52 × 0.36 mm
β = 100.859 (5)°

Data collection top

Bruker SMART CCD diffractometer	3702 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2002)	2929 reflections with I > 2σ(I)
T_min = 0.432, T_max = 0.611	R_int = 0.062
8019 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.100	H atoms treated by a mixture of independent and constrained refinement
S = 0.98	Δρ_max = 0.86 e Å⁻³
3702 reflections	Δρ_min = −0.59 e Å⁻³
283 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	0.71632 (5)	0.09770 (4)	0.66833 (2)	0.02738 (13)
O5	0.4196 (3)	0.1252 (2)	0.59395 (14)	0.0354 (5)
H5A	0.3260	0.0479	0.5847	0.053*
O3	1.5203 (3)	0.8764 (2)	0.69454 (14)	0.0384 (5)
O4	1.6651 (3)	0.8894 (2)	0.58459 (13)	0.0367 (5)
OW1	0.9119 (4)	0.1180 (3)	0.44343 (17)	0.0424 (6)
N2	0.9708 (4)	0.0659 (3)	0.76912 (15)	0.0270 (5)
N1	0.6579 (4)	0.2190 (3)	0.77760 (15)	0.0271 (5)
N3	0.9142 (5)	0.3624 (3)	1.07957 (17)	0.0425 (7)
C4	1.1058 (5)	0.1251 (3)	0.92035 (18)	0.0290 (7)
N4	1.2336 (5)	0.1937 (3)	1.07170 (17)	0.0410 (7)
C14	0.9630 (4)	0.1335 (3)	0.84604 (18)	0.0249 (6)
C8	0.9326 (5)	0.2869 (3)	1.00470 (19)	0.0325 (7)
C13	0.7948 (5)	0.2178 (3)	0.85096 (18)	0.0259 (6)
C12	0.5054 (5)	0.2965 (3)	0.7799 (2)	0.0340 (7)
H12A	0.4108	0.2974	0.7295	0.041*
C9	0.7811 (5)	0.2942 (3)	0.92828 (19)	0.0303 (7)
C5	1.0920 (5)	0.2042 (3)	1.00158 (18)	0.0327 (7)
C16	1.1651 (5)	0.4264 (3)	0.59565 (19)	0.0343 (7)
H16A	1.0786	0.4284	0.5407	0.041*
H16B	1.2742	0.3709	0.5865	0.041*
C19	1.5487 (5)	0.8164 (3)	0.6267 (2)	0.0323 (7)
C15	1.0173 (5)	0.3451 (3)	0.6441 (2)	0.0352 (7)
C10	0.6172 (5)	0.3738 (3)	0.9281 (2)	0.0383 (8)
H10A	0.6016	0.4249	0.9786	0.046*
C2	1.2673 (5)	−0.0301 (4)	0.8352 (2)	0.0376 (8)
H2A	1.3682	−0.0879	0.8294	0.045*
C17	1.2817 (6)	0.5833 (3)	0.6374 (2)	0.0400 (8)
H17A	1.3581	0.5832	0.6944	0.048*
H17B	1.1738	0.6422	0.6414	0.048*
C3	1.2606 (5)	0.0399 (3)	0.9126 (2)	0.0350 (7)
H3B	1.3586	0.0314	0.9604	0.042*
C11	0.4807 (5)	0.3765 (4)	0.8541 (2)	0.0408 (8)
H11A	0.3733	0.4306	0.8532	0.049*
C18	1.4442 (5)	0.6551 (3)	0.5904 (2)	0.0391 (8)
H18A	1.5587	0.6008	0.5907	0.047*
H18B	1.3701	0.6468	0.5321	0.047*
C1	1.1200 (5)	−0.0139 (3)	0.7642 (2)	0.0331 (7)
H1A	1.1268	−0.0610	0.7113	0.040*
C7	1.0537 (6)	0.3505 (4)	1.1468 (2)	0.0487 (9)
H7A	1.0475	0.3999	1.1992	0.058*
C6	1.2114 (6)	0.2665 (4)	1.1429 (2)	0.0490 (10)
H6A	1.3045	0.2621	1.1929	0.059*
O2	0.8998 (3)	0.2189 (2)	0.60661 (13)	0.0366 (5)
O1	1.0269 (5)	0.3952 (3)	0.71797 (17)	0.0684 (9)
HWBA	0.923 (6)	0.152 (4)	0.492 (2)	0.044 (12)*
H5B	0.432 (6)	0.129 (4)	0.534 (2)	0.068 (12)*
HWA1	1.048 (6)	0.128 (4)	0.446 (2)	0.047 (11)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.0268 (2)	0.0244 (2)	0.0289 (2)	0.00223 (14)	0.00547 (14)	0.00410 (14)
O5	0.0308 (12)	0.0365 (13)	0.0356 (13)	0.0039 (10)	0.0020 (10)	0.0083 (10)
O3	0.0386 (13)	0.0318 (12)	0.0401 (13)	0.0035 (10)	0.0087 (11)	−0.0027 (10)
O4	0.0349 (12)	0.0303 (12)	0.0446 (13)	−0.0004 (10)	0.0136 (11)	0.0108 (10)
OW1	0.0350 (15)	0.0536 (16)	0.0338 (15)	0.0065 (12)	0.0050 (12)	0.0011 (12)
N2	0.0261 (13)	0.0256 (13)	0.0289 (14)	0.0040 (11)	0.0091 (11)	0.0031 (11)
N1	0.0236 (13)	0.0245 (13)	0.0328 (14)	0.0042 (10)	0.0061 (11)	0.0065 (11)
N3	0.0527 (18)	0.0371 (16)	0.0354 (16)	0.0053 (14)	0.0122 (14)	0.0025 (13)
C4	0.0263 (16)	0.0296 (16)	0.0292 (16)	0.0021 (13)	0.0052 (13)	0.0058 (13)
N4	0.0421 (17)	0.0427 (17)	0.0339 (16)	0.0041 (13)	0.0016 (13)	0.0101 (13)
C14	0.0228 (15)	0.0236 (15)	0.0274 (15)	0.0014 (12)	0.0060 (12)	0.0059 (12)
C8	0.0378 (18)	0.0279 (16)	0.0291 (17)	0.0018 (14)	0.0090 (14)	0.0025 (14)
C13	0.0260 (15)	0.0217 (15)	0.0292 (16)	0.0019 (12)	0.0072 (13)	0.0053 (13)
C12	0.0324 (17)	0.0325 (17)	0.0392 (18)	0.0091 (14)	0.0075 (14)	0.0119 (15)
C9	0.0323 (17)	0.0264 (16)	0.0324 (17)	0.0042 (13)	0.0108 (14)	0.0044 (13)
C5	0.0352 (18)	0.0326 (17)	0.0276 (16)	0.0006 (14)	0.0060 (14)	0.0078 (14)
C16	0.0361 (18)	0.0279 (16)	0.0365 (18)	0.0015 (14)	0.0083 (14)	0.0057 (14)
C19	0.0267 (16)	0.0268 (16)	0.0419 (19)	0.0029 (13)	0.0059 (14)	0.0084 (15)
C15	0.0403 (19)	0.0304 (18)	0.0350 (19)	0.0052 (15)	0.0127 (15)	0.0048 (15)
C10	0.0413 (19)	0.0342 (18)	0.0414 (19)	0.0124 (15)	0.0142 (16)	0.0013 (15)
C2	0.0313 (17)	0.0433 (19)	0.046 (2)	0.0154 (15)	0.0149 (15)	0.0145 (16)
C17	0.049 (2)	0.0263 (17)	0.0423 (19)	−0.0011 (15)	0.0166 (17)	0.0046 (15)
C3	0.0296 (17)	0.0410 (19)	0.0364 (18)	0.0103 (15)	0.0042 (14)	0.0142 (15)
C11	0.0358 (19)	0.0358 (19)	0.054 (2)	0.0137 (16)	0.0122 (17)	0.0087 (17)
C18	0.0419 (19)	0.0254 (17)	0.047 (2)	−0.0010 (15)	0.0146 (16)	0.0032 (15)
C1	0.0315 (17)	0.0321 (17)	0.0377 (18)	0.0086 (14)	0.0129 (14)	0.0045 (14)
C7	0.066 (3)	0.044 (2)	0.0270 (18)	0.0023 (19)	0.0057 (18)	−0.0015 (16)
C6	0.060 (2)	0.047 (2)	0.0292 (19)	−0.0039 (19)	−0.0007 (17)	0.0064 (17)
O2	0.0386 (13)	0.0284 (12)	0.0351 (12)	−0.0076 (10)	0.0089 (10)	0.0017 (10)
O1	0.087 (2)	0.0472 (16)	0.0611 (18)	−0.0163 (15)	0.0381 (17)	−0.0080 (14)

Geometric parameters (Å, º) top

Zn1—O2	1.987 (2)	C13—C9	1.394 (4)
Zn1—N1	2.120 (3)	C12—C11	1.390 (4)
Zn1—O5	2.137 (2)	C12—H12A	0.9300
Zn1—O4ⁱ	2.154 (2)	C9—C10	1.401 (4)
Zn1—N2	2.188 (2)	C16—C15	1.510 (4)
Zn1—O3ⁱ	2.347 (2)	C16—C17	1.513 (4)
Zn1—C19ⁱ	2.588 (3)	C16—H16A	0.9700
O5—H5A	0.8200	C16—H16B	0.9700
O5—H5B	1.00 (4)	C19—C18	1.514 (4)
O3—C19	1.237 (4)	C19—Zn1ⁱⁱ	2.588 (3)
O3—Zn1ⁱⁱ	2.347 (2)	C15—O1	1.223 (4)
O4—C19	1.276 (4)	C15—O2	1.272 (4)
O4—Zn1ⁱⁱ	2.154 (2)	C10—C11	1.363 (4)
OW1—HWBA	0.79 (4)	C10—H10A	0.9300
OW1—HWA1	0.85 (4)	C2—C3	1.358 (4)
N2—C1	1.330 (4)	C2—C1	1.400 (4)
N2—C14	1.345 (4)	C2—H2A	0.9300
N1—C12	1.329 (4)	C17—C18	1.518 (4)
N1—C13	1.351 (4)	C17—H17A	0.9700
N3—C7	1.314 (4)	C17—H17B	0.9700
N3—C8	1.367 (4)	C3—H3B	0.9300
C4—C14	1.401 (4)	C11—H11A	0.9300
C4—C3	1.401 (4)	C18—H18A	0.9700
C4—C5	1.459 (4)	C18—H18B	0.9700
N4—C6	1.314 (4)	C1—H1A	0.9300
N4—C5	1.352 (4)	C7—C6	1.401 (5)
C14—C13	1.463 (4)	C7—H7A	0.9300
C8—C5	1.401 (4)	C6—H6A	0.9300
C8—C9	1.452 (4)

O2—Zn1—N1	114.24 (9)	C15—C16—C17	115.5 (3)
O2—Zn1—O5	92.64 (9)	C15—C16—H16A	108.4
N1—Zn1—O5	90.76 (9)	C17—C16—H16A	108.4
O2—Zn1—O4ⁱ	96.87 (9)	C15—C16—H16B	108.4
N1—Zn1—O4ⁱ	148.89 (9)	C17—C16—H16B	108.4
O5—Zn1—O4ⁱ	87.08 (8)	H16A—C16—H16B	107.5
O2—Zn1—N2	100.06 (10)	O3—C19—O4	120.8 (3)
N1—Zn1—N2	77.41 (9)	O3—C19—C18	121.2 (3)
O5—Zn1—N2	165.34 (9)	O4—C19—C18	118.0 (3)
O4ⁱ—Zn1—N2	98.53 (9)	O3—C19—Zn1ⁱⁱ	64.86 (16)
O2—Zn1—O3ⁱ	154.65 (8)	O4—C19—Zn1ⁱⁱ	56.11 (15)
N1—Zn1—O3ⁱ	91.04 (9)	C18—C19—Zn1ⁱⁱ	172.5 (2)
O5—Zn1—O3ⁱ	88.79 (9)	O1—C15—O2	122.9 (3)
O4ⁱ—Zn1—O3ⁱ	57.90 (8)	O1—C15—C16	120.1 (3)
N2—Zn1—O3ⁱ	82.87 (9)	O2—C15—C16	116.8 (3)
Zn1—O5—H5A	109.5	C11—C10—C9	120.1 (3)
Zn1—O5—H5B	111 (2)	C11—C10—H10A	120.0
H5A—O5—H5B	98.4	C9—C10—H10A	120.0
C19—O3—Zn1ⁱⁱ	86.64 (18)	C3—C2—C1	119.0 (3)
C19—O4—Zn1ⁱⁱ	94.44 (19)	C3—C2—H2A	120.5
HWBA—OW1—HWA1	96 (3)	C1—C2—H2A	120.5
C1—N2—C14	117.9 (3)	C16—C17—C18	113.3 (3)
C1—N2—Zn1	129.1 (2)	C16—C17—H17A	108.9
C14—N2—Zn1	112.93 (18)	C18—C17—H17A	108.9
C12—N1—C13	118.3 (3)	C16—C17—H17B	108.9
C12—N1—Zn1	126.4 (2)	C18—C17—H17B	108.9
C13—N1—Zn1	115.27 (18)	H17A—C17—H17B	107.7
C7—N3—C8	115.4 (3)	C2—C3—C4	119.8 (3)
C14—C4—C3	117.3 (3)	C2—C3—H3B	120.1
C14—C4—C5	120.3 (3)	C4—C3—H3B	120.1
C3—C4—C5	122.4 (3)	C10—C11—C12	118.6 (3)
C6—N4—C5	115.4 (3)	C10—C11—H11A	120.7
N2—C14—C4	123.1 (3)	C12—C11—H11A	120.7
N2—C14—C13	117.5 (2)	C19—C18—C17	114.4 (3)
C4—C14—C13	119.4 (3)	C19—C18—H18A	108.7
N3—C8—C5	121.1 (3)	C17—C18—H18A	108.7
N3—C8—C9	118.0 (3)	C19—C18—H18B	108.7
C5—C8—C9	120.8 (3)	C17—C18—H18B	108.7
N1—C13—C9	122.5 (3)	H18A—C18—H18B	107.6
N1—C13—C14	116.9 (2)	N2—C1—C2	122.9 (3)
C9—C13—C14	120.6 (3)	N2—C1—H1A	118.6
N1—C12—C11	123.0 (3)	C2—C1—H1A	118.6
N1—C12—H12A	118.5	N3—C7—C6	122.9 (3)
C11—C12—H12A	118.5	N3—C7—H7A	118.6
C13—C9—C10	117.5 (3)	C6—C7—H7A	118.6
C13—C9—C8	119.4 (3)	N4—C6—C7	122.9 (3)
C10—C9—C8	123.1 (3)	N4—C6—H6A	118.5
N4—C5—C8	122.2 (3)	C7—C6—H6A	118.5
N4—C5—C4	118.4 (3)	C15—O2—Zn1	119.5 (2)
C8—C5—C4	119.4 (3)

O2—Zn1—N2—C1	−69.5 (3)	C14—C13—C9—C8	−1.3 (4)
N1—Zn1—N2—C1	177.7 (3)	N3—C8—C9—C13	−179.6 (3)
O5—Zn1—N2—C1	140.8 (3)	C5—C8—C9—C13	0.0 (4)
O4ⁱ—Zn1—N2—C1	29.1 (3)	N3—C8—C9—C10	−0.4 (5)
O3ⁱ—Zn1—N2—C1	85.0 (3)	C5—C8—C9—C10	179.2 (3)
C19ⁱ—Zn1—N2—C1	57.9 (3)	C6—N4—C5—C8	0.0 (5)
O2—Zn1—N2—C14	113.54 (19)	C6—N4—C5—C4	−179.4 (3)
N1—Zn1—N2—C14	0.73 (18)	N3—C8—C5—N4	0.5 (5)
O5—Zn1—N2—C14	−36.1 (4)	C9—C8—C5—N4	−179.1 (3)
O4ⁱ—Zn1—N2—C14	−147.87 (19)	N3—C8—C5—C4	179.9 (3)
O3ⁱ—Zn1—N2—C14	−91.94 (19)	C9—C8—C5—C4	0.2 (4)
C19ⁱ—Zn1—N2—C14	−119.0 (2)	C14—C4—C5—N4	−179.7 (3)
O2—Zn1—N1—C12	82.8 (3)	C3—C4—C5—N4	−0.4 (5)
O5—Zn1—N1—C12	−10.4 (2)	C14—C4—C5—C8	0.9 (4)
O4ⁱ—Zn1—N1—C12	−96.0 (3)	C3—C4—C5—C8	−179.8 (3)
N2—Zn1—N1—C12	178.3 (3)	Zn1ⁱⁱ—O3—C19—O4	4.3 (3)
O3ⁱ—Zn1—N1—C12	−99.2 (2)	Zn1ⁱⁱ—O3—C19—C18	−174.8 (3)
C19ⁱ—Zn1—N1—C12	−96.7 (3)	Zn1ⁱⁱ—O4—C19—O3	−4.7 (3)
O2—Zn1—N1—C13	−95.7 (2)	Zn1ⁱⁱ—O4—C19—C18	174.5 (2)
O5—Zn1—N1—C13	171.1 (2)	C17—C16—C15—O1	−13.0 (5)
O4ⁱ—Zn1—N1—C13	85.5 (3)	C17—C16—C15—O2	172.8 (3)
N2—Zn1—N1—C13	−0.17 (19)	C13—C9—C10—C11	−1.0 (5)
O3ⁱ—Zn1—N1—C13	82.3 (2)	C8—C9—C10—C11	179.8 (3)
C19ⁱ—Zn1—N1—C13	84.8 (2)	C15—C16—C17—C18	174.5 (3)
C1—N2—C14—C4	0.8 (4)	C1—C2—C3—C4	0.8 (5)
Zn1—N2—C14—C4	178.2 (2)	C14—C4—C3—C2	0.0 (5)
C1—N2—C14—C13	−178.5 (2)	C5—C4—C3—C2	−179.3 (3)
Zn1—N2—C14—C13	−1.2 (3)	C9—C10—C11—C12	1.3 (5)
C3—C4—C14—N2	−0.9 (4)	N1—C12—C11—C10	−0.8 (5)
C5—C4—C14—N2	178.4 (3)	O3—C19—C18—C17	8.1 (4)
C3—C4—C14—C13	178.4 (3)	O4—C19—C18—C17	−171.1 (3)
C5—C4—C14—C13	−2.2 (4)	Zn1ⁱⁱ—C19—C18—C17	−133.6 (16)
C7—N3—C8—C5	−0.4 (5)	C16—C17—C18—C19	175.0 (3)
C7—N3—C8—C9	179.2 (3)	C14—N2—C1—C2	0.1 (4)
C12—N1—C13—C9	0.2 (4)	Zn1—N2—C1—C2	−176.8 (2)
Zn1—N1—C13—C9	178.8 (2)	C3—C2—C1—N2	−0.9 (5)
C12—N1—C13—C14	−179.0 (2)	C8—N3—C7—C6	0.0 (5)
Zn1—N1—C13—C14	−0.4 (3)	C5—N4—C6—C7	−0.4 (5)
N2—C14—C13—N1	1.1 (4)	N3—C7—C6—N4	0.5 (6)
C4—C14—C13—N1	−178.3 (3)	O1—C15—O2—Zn1	1.6 (5)
N2—C14—C13—C9	−178.1 (3)	C16—C15—O2—Zn1	175.6 (2)
C4—C14—C13—C9	2.5 (4)	N1—Zn1—O2—C15	18.7 (3)
C13—N1—C12—C11	0.1 (4)	O5—Zn1—O2—C15	110.7 (2)
Zn1—N1—C12—C11	−178.3 (2)	O4ⁱ—Zn1—O2—C15	−161.9 (2)
N1—C13—C9—C10	0.2 (4)	N2—Zn1—O2—C15	−61.9 (2)
C14—C13—C9—C10	179.4 (3)	O3ⁱ—Zn1—O2—C15	−156.5 (2)
N1—C13—C9—C8	179.5 (3)	C19ⁱ—Zn1—O2—C15	−161.8 (2)

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
O5—H5A···OW1ⁱⁱⁱ	0.82	1.89	2.702 (3)	173
O5—H5B···O4^iv	1.00 (4)	1.91 (4)	2.856 (3)	157 (3)
OW1—HWA1···O4^v	0.85 (4)	2.03 (4)	2.840 (4)	161 (3)
OW1—HWBA···O2	0.79 (4)	1.95 (4)	2.733 (4)	170 (4)

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

Experimental details

Crystal data
Chemical formula	[Zn(C₅H₆O₄)(C₁₄H₈N₄)(H₂O)]·H₂O
M_r	463.74
Crystal system, space group	Triclinic, P1
Temperature (K)	292
a, b, c (Å)	6.397 (3), 9.384 (5), 16.409 (8)
α, β, γ (°)	98.067 (5), 100.859 (5), 101.274 (5)
V (Å³)	932.5 (8)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.37
Crystal size (mm)	0.78 × 0.52 × 0.36

Data collection
Diffractometer	Bruker SMART CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2002)
T_min, T_max	0.432, 0.611
No. of measured, independent and observed [I > 2σ(I)] reflections	8019, 3702, 2929
R_int	0.062
(sin θ/λ)_max (Å⁻¹)	0.619

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.100, 0.98
No. of reflections	3702
No. of parameters	283
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.86, −0.59

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Zn1—O2	1.987 (2)	Zn1—O4ⁱ	2.154 (2)
Zn1—N1	2.120 (3)	Zn1—N2	2.188 (2)
Zn1—O5	2.137 (2)	Zn1—O3ⁱ	2.347 (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
O5—H5A···OW1ⁱⁱ	0.82	1.89	2.702 (3)	173
O5—H5B···O4ⁱⁱⁱ	1.00 (4)	1.91 (4)	2.856 (3)	157 (3)
OW1—HWA1···O4^iv	0.85 (4)	2.03 (4)	2.840 (4)	161 (3)
OW1—HWBA···O2	0.79 (4)	1.95 (4)	2.733 (4)	170 (4)

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

Acknowledgements

The author thanks Baicheng Normal University for supporting this work.

References

Bruker (2002). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Dickeson, J. E. & Summers, L. A. (1970). Aust. J. Chem. 23, 1023–1027. CrossRef CAS Web of Science Google Scholar
Fang-Wei & Mei, Z.-M. (2007). Acta Cryst. E63, m3098–m3099. Google Scholar
Li, C.-B., Fang, W., Gao, G.-G. & Liu, B. (2006). Acta Cryst. E62, m1312–m1314. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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