Bis(4,4′-bipyrid­yl)bis{2-[4,6-bis­(carboxy­methyl­sulfan­yl)-1,3,5-triazin-2-ylsulfan­yl]acetato}zinc(II)

Wang, S.; Yang, Y.; Li, D.; Dou, J.; Wang, D.

doi:10.1107/S160053681000735X

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 4| April 2010| Pages m370-m371

doi:10.1107/S160053681000735X

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Bis(4,4′-bipyridyl)bis{2-[4,6-bis(carboxymethylsulfanyl)-1,3,5-triazin-2-ylsulfanyl]acetato}zinc(II)

Suna Wang,^a ^* Yan Yang,^a Dacheng Li,^a Jianmin Dou ^a and Daqi Wang ^a

^aCollege of Chemistry and Chemical Engineering, Liaocheng University, Liaocheng 252059, People's Republic of China
^*Correspondence e-mail: wangsuna@lcu.edu.cn

(Received 3 December 2009; accepted 26 February 2010; online 6 March 2010)

In the title compound, [Zn(C₉H₈N₃O₆S₃)₂(C₁₀H₈N₂)₂], the central Zn^II ion, situated on a center of inversion, adopts an octahedral geometry coordinated by four O atoms from two carboxylate groups and two carboxylic groups of two symmetry-related TTTA ligands and two N atoms from two bpy molecules {TTTA is 2,2′,2′′-[1,3,5-triazine-2,4,6-triyltris(sulfanediyl)]triacetic acid and bpy is 4,4′-bipyridine}. These mononuclear units are connected through complementary O—H⋯X hydrogen bonds, as well as through weak C—H⋯X (X = O and N) interactions, resulting in a three-dimensional supramolecular architecture.

Related literature

For crystal engineering of carboxylates, see: Moulton & Zaworotko (2001 ); Rao et al. (2004 ); Ferey et al. (2005 ). For interactions involved in the self-assembly process, see: Braga & Grepioni (2000 ); Roesky & Andruh (2003 ); Chen et al. (2009 ). For our work on the coordination chemistry of semirigid polycarboxylate ligands with functional groups introduced between the aromatic ring and carboxylate groups, see: Wang et al. (2007 ); Hong et al. (2005 ); Sun et al. (2007 ).

Experimental

Crystal data

[Zn(C₉H₈N₃O₆S₃)₂(C₁₀H₈N₂)₂]
M_r = 1078.47
Triclinic, $[P \overline 1]$
a = 8.6025 (7) Å
b = 8.7606 (7) Å
c = 15.3187 (12) Å
α = 99.518 (1)°
β = 105.802 (2)°
γ = 98.805 (1)°
V = 1071.41 (15) Å³
Z = 1
Mo Kα radiation
μ = 0.94 mm⁻¹
T = 293 K
0.28 × 0.24 × 0.23 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.81, T_max = 0.84
5465 measured reflections
3745 independent reflections
3103 reflections with I > 2σ(I)
R_int = 0.067

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.116
S = 1.05
3745 reflections
306 parameters
H-atom parameters constrained
Δρ_max = 0.55 e Å⁻³
Δρ_min = −0.63 e Å⁻³

Table 1
Selected bond lengths (Å)

Zn1—O3	2.1145 (19)
Zn1—N4	2.135 (2)
Zn1—O1	2.189 (2)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O4ⁱ	0.82	1.64	2.460 (3)	175
O5—H5⋯N5ⁱⁱ	0.82	1.74	2.554 (3)	174
C13—H13⋯O6ⁱⁱⁱ	0.93	2.47	3.335 (4)	156
C19—H19⋯O6ⁱⁱⁱ	0.93	2.34	3.245 (4)	164
C6—H6A⋯N1^iv	0.97	2.58	3.533 (4)	168
Symmetry codes: (i) -x+1, -y-1, -z+1; (ii) -x, -y+1, -z+2; (iii) -x+1, -y+1, -z+2; (iv) x+1, y, z.

Data collection: SMART (Bruker, 2000 ); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681000735X/rn2067sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681000735X/rn2067Isup2.hkl

checkCIF report

Comment top

Recent years have witnessed rapid development of the construction of metal-organic assemblies with fascinating structures and properties in coordination chemistry and crystal engineering. (Moulton & Zaworotko, 2001; Rao et al., 2004; Ferey et al., 2005). Besides metal-ligand coordination bonding, various kinds of intermolecular weak interactions, such as hydrogen bonds, weak C—H···X (X = O, N, π) interactions and π···π stacking, are also vital in the self-assembly process. (Braga & Grepioni, 2000; Roesky & Andruh, 2003; Chen et al., 2009) Our interest is the coordination chemistry of semirigid polycarboxylate ligands by introducing functional groups between the aromatic ring and carboxylate groups (Hong et al., 2005; Wang et al., 2007; Sun et al., 2007).

Herein we report the title compound [Zn(TTTA)₂(bpy)₂] (TTTA = 2,2',2''-[1,3,5-triazine-2,4,6-triyltris(thio)]tris-acetic acid, bpy = 4,4'-bipyridine), as illustrated in Scheme 1 and Figure 1. The Zn^II ion, situated on a center of inversion, adopts octahedral geometry with four oxygen atoms from two carboxylate groups and two carboxylic groups of two different TTTA ligands and two nitrogen atoms from two coordinated bpy molecules. Only one carboxylate group of the TTTA ligand is deprotonated and coordinated to the metal center in a monodentate mode. The atoms in the central triazine ring are almost coplanar with a very small deviation of only 0.0085 Å from the mean plane and the dihedral angle of the carboxylate group with the triazine ring is 75.6 (2)°. The other two -COOH groups, one of which is coordinated and the other uncoordinated, form the dihedral angles of 80.0 (2) and 175.0 (4)° with the triazine ring, respectively.

As shown in Figure 2, significant O—H···N hydrogen bonding interactions are generated between hydroxyl groups (O5-H5) of the carboxylic acid and uncoordinated nitrogen atom (N5) from adjacent molecules. As a result, one-dimensional hinged chains containing M₂L₂(bpy)₂ macrocyclic rings are formed along the b axis. These chains are further linked together in a parallel fashion to form a two-dimensional sheet through O—H···O hydrogen bonds between the carboxylate group (O2) and carboxyl oxygen atom (O4) from adjacent chains. Between neighboring sheets, bpy (C13 and C18) CH groups form weak C—H···O weak interactions with TTTA carboxyl oxygen atoms (O6). Simultaneously, these sheets are consolidated further through weak C—H···N interactions between CH₂ groups (C6) and N atoms (N1) of the triazine ring (Figure 3 and Table 2). Thus, the mononuclear units are connected together through the complementary interactions of several kinds of hydrogen bonds, which ultimately extend into a three-dimensional framework.

Related literature top

For crystal engineering of carboxylates, see: Moulton & Zaworotko (2001); Rao et al. (2004); Ferey et al. (2005). For interactions involved in the self-assembly process, see: Braga & Grepioni (2000); Roesky & Andruh (2003); Chen et al. (2009). For our work on the coordination chemistry of semirigid polycarboxylate ligands with functional groups introduced between the aromatic ring and carboxylate groups, see: Wang et al. (2007); Hong et al. (2005); Sun et al. (2007).

Experimental top

A mixture of TTTA (0.025 mmol, 0.010 g), bpy (0.05 mmol, 0.008 g), Zn(NO₃)₂.6H₂O (0.025 mmol, 0.013 g) with H₂O (10 ml) was placed in a Parr Teflon-lined stainless steel vessel and heated to 80 °C for 24 h. Then the reaction system was cooled to room temperature slowly and light yellow block crystals were obtained. After filtration, the crystals were washed with water and dried in air. Elemental analysis calculated for C₃₈H₃₂N₁₀O₁₂S₆Zn (Mr = 1078.47) : C 42.32, H 2.99, N 12.99%; found: C 42.13, H 2.92, N 13.08%.

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The local coordination environment for the Zn^II centers in 1. Hydrogen atoms have been omitted for clarity, and thermal ellipsoids are drawn at the 30% probability level. Selected bonds information is listed in Table 1. Symmetry codes: (i) 1-x, -y, 1-z.
	Fig. 2. View of the two-dimensional layer, constructed by O—H···N and O—H···O hydrogen bonding between the adjacent mononuclears. Only the hydrogen atoms in hydrogen bonds are shown for clarity.
	Fig. 3. View of the C—H···O and C—H···N weak interactions between the layers. Only the hydrogen atoms in hydrogen bonds are shown for clarity.

Bis(4,4'-bipyridyl)bis{2-[4,6-bis(carboxymethylsulfanyl)-1,3,5-triazin-2- ylsulfanyl]acetato}zinc(II) top

Crystal data top

[Zn(C₉H₈N₃O₆S₃)₂(C₁₀H₈N₂)₂]	Z = 1
M_r = 1078.47	F(000) = 552
Triclinic, P1	D_x = 1.671 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.6025 (7) Å	Cell parameters from 2836 reflections
b = 8.7606 (7) Å	θ = 2.5–28.1°
c = 15.3187 (12) Å	µ = 0.94 mm⁻¹
α = 99.518 (1)°	T = 293 K
β = 105.802 (2)°	Block, colorless
γ = 98.805 (1)°	0.28 × 0.24 × 0.23 mm
V = 1071.41 (15) Å³

Data collection top

Bruker SMART APEX CCD diffractometer	3745 independent reflections
Radiation source: fine-focus sealed tube	3103 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.067
phi and ω scans	θ_max = 25.0°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→10
T_min = 0.81, T_max = 0.84	k = −10→9
5465 measured reflections	l = −18→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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.116	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0632P)²] where P = (F_o² + 2F_c²)/3
3745 reflections	(Δ/σ)_max = 0.001
306 parameters	Δρ_max = 0.55 e Å⁻³
0 restraints	Δρ_min = −0.63 e Å⁻³

Crystal data top

[Zn(C₉H₈N₃O₆S₃)₂(C₁₀H₈N₂)₂]	γ = 98.805 (1)°
M_r = 1078.47	V = 1071.41 (15) Å³
Triclinic, P1	Z = 1
a = 8.6025 (7) Å	Mo Kα radiation
b = 8.7606 (7) Å	µ = 0.94 mm⁻¹
c = 15.3187 (12) Å	T = 293 K
α = 99.518 (1)°	0.28 × 0.24 × 0.23 mm
β = 105.802 (2)°

Data collection top

Bruker SMART APEX CCD diffractometer	3745 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3103 reflections with I > 2σ(I)
T_min = 0.81, T_max = 0.84	R_int = 0.067
5465 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.116	H-atom parameters constrained
S = 1.05	Δρ_max = 0.55 e Å⁻³
3745 reflections	Δρ_min = −0.63 e Å⁻³
306 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	0.5000	0.0000	0.5000	0.02725 (17)
N1	0.1818 (3)	−0.1424 (3)	0.74960 (17)	0.0324 (6)
N2	0.4260 (3)	−0.1972 (3)	0.71830 (15)	0.0265 (5)
N3	0.4458 (3)	−0.0022 (3)	0.85212 (16)	0.0276 (6)
N4	0.3822 (3)	0.1179 (3)	0.58899 (16)	0.0260 (5)
N5	0.0151 (3)	0.5510 (3)	0.88027 (19)	0.0402 (7)
O1	0.3126 (3)	−0.2111 (2)	0.48345 (15)	0.0365 (5)
O2	0.3316 (3)	−0.4383 (2)	0.40496 (14)	0.0368 (5)
H2	0.3378	−0.5271	0.4142	0.044*
O3	0.6664 (2)	−0.0338 (2)	0.62169 (13)	0.0291 (5)
O4	0.6623 (3)	−0.2886 (2)	0.57706 (14)	0.0352 (5)
O5	0.1025 (3)	0.2799 (3)	1.01154 (16)	0.0456 (6)
H5	0.0713	0.3389	1.0476	0.055*
O6	0.3494 (3)	0.4151 (3)	1.09911 (19)	0.0634 (8)
S1	0.13117 (9)	−0.35869 (9)	0.60274 (5)	0.0338 (2)
S2	0.72472 (9)	−0.03437 (9)	0.82517 (5)	0.0308 (2)
S3	0.17169 (10)	0.05612 (10)	0.89085 (6)	0.0401 (2)
C1	0.2626 (3)	−0.2188 (3)	0.69989 (19)	0.0252 (6)
C2	0.5103 (3)	−0.0856 (3)	0.79407 (19)	0.0247 (6)
C3	0.2811 (4)	−0.0367 (3)	0.8256 (2)	0.0287 (7)
C4	0.2717 (4)	−0.4370 (3)	0.5489 (2)	0.0267 (6)
H4A	0.3749	−0.4300	0.5965	0.032*
H4B	0.2259	−0.5481	0.5205	0.032*
C5	0.3071 (4)	−0.3530 (3)	0.4759 (2)	0.0272 (6)
C6	0.7620 (4)	−0.1775 (3)	0.73879 (19)	0.0282 (7)
H6A	0.8804	−0.1675	0.7521	0.034*
H6B	0.7170	−0.2824	0.7447	0.034*
C7	0.6901 (3)	−0.1647 (3)	0.63890 (19)	0.0250 (6)
C8	0.3335 (4)	0.2042 (4)	0.9770 (2)	0.0325 (7)
H8A	0.4075	0.1532	1.0167	0.039*
H8B	0.3968	0.2662	0.9465	0.039*
C9	0.2604 (4)	0.3118 (4)	1.0352 (2)	0.0346 (7)
C10	0.2189 (4)	0.1151 (4)	0.5617 (2)	0.0334 (7)
H10	0.1555	0.0562	0.5031	0.040*
C11	0.1411 (4)	0.1955 (4)	0.6167 (2)	0.0329 (7)
H11	0.0278	0.1896	0.5950	0.039*
C12	0.2330 (4)	0.2856 (3)	0.7048 (2)	0.0269 (6)
C13	0.4010 (4)	0.2880 (3)	0.7317 (2)	0.0309 (7)
H13	0.4681	0.3470	0.7896	0.037*
C14	0.4687 (4)	0.2032 (3)	0.6729 (2)	0.0297 (7)
H14	0.5815	0.2061	0.6932	0.036*
C15	0.1554 (4)	0.3774 (3)	0.7653 (2)	0.0277 (6)
C16	−0.0110 (4)	0.3372 (4)	0.7560 (2)	0.0388 (8)
H16	−0.0784	0.2503	0.7110	0.047*
C17	−0.0762 (4)	0.4272 (4)	0.8142 (2)	0.0447 (9)
H17	−0.1885	0.3999	0.8068	0.054*
C18	0.1757 (4)	0.5904 (4)	0.8904 (2)	0.0383 (8)
H18	0.2401	0.6770	0.9367	0.046*
C19	0.2497 (4)	0.5074 (4)	0.8345 (2)	0.0352 (7)
H19	0.3622	0.5382	0.8431	0.042*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.0323 (3)	0.0258 (3)	0.0252 (3)	0.0085 (2)	0.0130 (2)	0.0003 (2)
N1	0.0275 (14)	0.0362 (14)	0.0309 (14)	0.0065 (11)	0.0110 (11)	−0.0026 (11)
N2	0.0244 (13)	0.0290 (13)	0.0244 (13)	0.0052 (11)	0.0077 (10)	0.0012 (11)
N3	0.0256 (13)	0.0322 (13)	0.0241 (13)	0.0078 (11)	0.0089 (10)	−0.0001 (11)
N4	0.0286 (13)	0.0230 (12)	0.0266 (13)	0.0066 (10)	0.0109 (11)	0.0013 (10)
N5	0.0369 (16)	0.0439 (16)	0.0404 (16)	0.0147 (13)	0.0159 (13)	−0.0018 (13)
O1	0.0389 (13)	0.0255 (12)	0.0460 (13)	0.0062 (9)	0.0162 (10)	0.0056 (10)
O2	0.0511 (14)	0.0299 (11)	0.0338 (12)	0.0098 (11)	0.0192 (10)	0.0071 (10)
O3	0.0352 (12)	0.0253 (10)	0.0276 (11)	0.0089 (9)	0.0110 (9)	0.0028 (9)
O4	0.0466 (14)	0.0284 (11)	0.0301 (12)	0.0123 (10)	0.0124 (10)	0.0000 (9)
O5	0.0359 (14)	0.0519 (15)	0.0437 (14)	0.0148 (11)	0.0142 (11)	−0.0129 (11)
O6	0.0462 (16)	0.0648 (17)	0.0614 (18)	0.0071 (14)	0.0157 (13)	−0.0295 (14)
S1	0.0239 (4)	0.0386 (5)	0.0307 (4)	−0.0020 (3)	0.0090 (3)	−0.0085 (3)
S2	0.0220 (4)	0.0406 (5)	0.0236 (4)	0.0047 (3)	0.0050 (3)	−0.0051 (3)
S3	0.0272 (4)	0.0481 (5)	0.0387 (5)	0.0078 (4)	0.0134 (4)	−0.0135 (4)
C1	0.0253 (15)	0.0254 (15)	0.0257 (15)	0.0063 (12)	0.0099 (12)	0.0032 (12)
C2	0.0250 (15)	0.0265 (15)	0.0222 (14)	0.0062 (12)	0.0070 (12)	0.0034 (12)
C3	0.0281 (16)	0.0310 (16)	0.0275 (16)	0.0085 (13)	0.0107 (13)	0.0022 (13)
C4	0.0273 (15)	0.0241 (14)	0.0272 (15)	0.0048 (12)	0.0096 (12)	−0.0005 (12)
C5	0.0266 (16)	0.0238 (16)	0.0294 (16)	0.0050 (12)	0.0085 (12)	0.0013 (12)
C6	0.0248 (15)	0.0309 (16)	0.0289 (16)	0.0088 (13)	0.0090 (12)	0.0023 (13)
C7	0.0232 (15)	0.0267 (15)	0.0259 (15)	0.0057 (12)	0.0113 (12)	0.0013 (12)
C8	0.0281 (16)	0.0381 (17)	0.0300 (16)	0.0106 (14)	0.0094 (13)	−0.0002 (14)
C9	0.0316 (18)	0.0373 (18)	0.0320 (17)	0.0084 (14)	0.0100 (14)	−0.0018 (14)
C10	0.0335 (17)	0.0319 (16)	0.0318 (17)	0.0054 (14)	0.0117 (14)	−0.0030 (13)
C11	0.0290 (16)	0.0347 (17)	0.0329 (17)	0.0068 (13)	0.0112 (13)	−0.0013 (14)
C12	0.0293 (16)	0.0259 (15)	0.0274 (15)	0.0074 (12)	0.0118 (12)	0.0044 (12)
C13	0.0308 (17)	0.0325 (16)	0.0279 (16)	0.0080 (14)	0.0098 (13)	−0.0003 (13)
C14	0.0293 (16)	0.0312 (16)	0.0290 (16)	0.0094 (13)	0.0097 (13)	0.0033 (13)
C15	0.0287 (16)	0.0298 (15)	0.0258 (15)	0.0099 (13)	0.0099 (12)	0.0034 (12)
C16	0.0355 (18)	0.0409 (19)	0.0383 (19)	0.0095 (15)	0.0137 (15)	−0.0015 (15)
C17	0.0361 (19)	0.052 (2)	0.046 (2)	0.0134 (17)	0.0169 (16)	−0.0018 (17)
C18	0.0390 (19)	0.0377 (18)	0.0368 (18)	0.0103 (15)	0.0142 (15)	−0.0026 (15)
C19	0.0319 (17)	0.0356 (17)	0.0378 (18)	0.0089 (14)	0.0148 (14)	−0.0018 (14)

Geometric parameters (Å, º) top

Zn1—O3ⁱ	2.1145 (19)	S3—C3	1.739 (3)
Zn1—O3	2.1145 (19)	S3—C8	1.800 (3)
Zn1—N4ⁱ	2.135 (2)	C4—C5	1.507 (4)
Zn1—N4	2.135 (2)	C4—H4A	0.9700
Zn1—O1	2.189 (2)	C4—H4B	0.9700
Zn1—O1ⁱ	2.189 (2)	C6—C7	1.516 (4)
N1—C1	1.331 (4)	C6—H6A	0.9700
N1—C3	1.342 (4)	C6—H6B	0.9700
N2—C1	1.333 (4)	C8—C9	1.513 (4)
N2—C2	1.334 (3)	C8—H8A	0.9700
N3—C3	1.334 (4)	C8—H8B	0.9700
N3—C2	1.346 (4)	C10—C11	1.382 (4)
N4—C14	1.325 (4)	C10—H10	0.9300
N4—C10	1.347 (4)	C11—C12	1.394 (4)
N5—C17	1.327 (4)	C11—H11	0.9300
N5—C18	1.331 (4)	C12—C13	1.386 (4)
O1—C5	1.222 (3)	C12—C15	1.486 (4)
O2—C5	1.299 (3)	C13—C14	1.379 (4)
O2—H2	0.8200	C13—H13	0.9300
O3—C7	1.252 (3)	C14—H14	0.9300
O4—C7	1.261 (3)	C15—C16	1.383 (4)
O5—C9	1.279 (4)	C15—C19	1.388 (4)
O5—H5	0.8200	C16—C17	1.380 (4)
O6—C9	1.204 (4)	C16—H16	0.9300
S1—C1	1.747 (3)	C17—H17	0.9300
S1—C4	1.795 (3)	C18—C19	1.379 (4)
S2—C2	1.740 (3)	C18—H18	0.9300
S2—C6	1.797 (3)	C19—H19	0.9300

O3ⁱ—Zn1—O3	180.00 (7)	C7—C6—H6A	108.4
O3ⁱ—Zn1—N4ⁱ	86.91 (8)	S2—C6—H6A	108.4
O3—Zn1—N4ⁱ	93.09 (8)	C7—C6—H6B	108.4
O3ⁱ—Zn1—N4	93.09 (8)	S2—C6—H6B	108.4
O3—Zn1—N4	86.91 (8)	H6A—C6—H6B	107.4
N4ⁱ—Zn1—N4	180.00 (9)	O3—C7—O4	123.7 (3)
O3ⁱ—Zn1—O1	84.73 (8)	O3—C7—C6	119.5 (2)
O3—Zn1—O1	95.27 (8)	O4—C7—C6	116.8 (2)
N4ⁱ—Zn1—O1	94.10 (8)	C9—C8—S3	110.2 (2)
N4—Zn1—O1	85.90 (8)	C9—C8—H8A	109.6
O3ⁱ—Zn1—O1ⁱ	95.27 (8)	S3—C8—H8A	109.6
O3—Zn1—O1ⁱ	84.73 (8)	C9—C8—H8B	109.6
N4ⁱ—Zn1—O1ⁱ	85.90 (8)	S3—C8—H8B	109.6
N4—Zn1—O1ⁱ	94.10 (8)	H8A—C8—H8B	108.1
O1—Zn1—O1ⁱ	180.00 (7)	O6—C9—O5	125.3 (3)
C1—N1—C3	113.8 (3)	O6—C9—C8	120.2 (3)
C1—N2—C2	113.8 (2)	O5—C9—C8	114.4 (3)
C3—N3—C2	113.4 (2)	N4—C10—C11	123.2 (3)
C14—N4—C10	116.8 (3)	N4—C10—H10	118.4
C14—N4—Zn1	121.0 (2)	C11—C10—H10	118.4
C10—N4—Zn1	122.14 (19)	C10—C11—C12	119.7 (3)
C17—N5—C18	118.6 (3)	C10—C11—H11	120.1
C5—O1—Zn1	136.6 (2)	C12—C11—H11	120.1
C5—O2—H2	109.5	C13—C12—C11	116.5 (3)
C7—O3—Zn1	125.67 (18)	C13—C12—C15	121.9 (3)
C9—O5—H5	109.5	C11—C12—C15	121.7 (3)
C1—S1—C4	103.09 (14)	C14—C13—C12	120.1 (3)
C2—S2—C6	100.14 (13)	C14—C13—H13	119.9
C3—S3—C8	101.90 (14)	C12—C13—H13	119.9
N1—C1—N2	126.4 (3)	N4—C14—C13	123.7 (3)
N1—C1—S1	113.1 (2)	N4—C14—H14	118.1
N2—C1—S1	120.6 (2)	C13—C14—H14	118.1
N2—C2—N3	126.3 (3)	C16—C15—C19	117.5 (3)
N2—C2—S2	120.1 (2)	C16—C15—C12	122.0 (3)
N3—C2—S2	113.6 (2)	C19—C15—C12	120.5 (3)
N3—C3—N1	126.3 (3)	C17—C16—C15	119.4 (3)
N3—C3—S3	121.1 (2)	C17—C16—H16	120.3
N1—C3—S3	112.6 (2)	C15—C16—H16	120.3
C5—C4—S1	113.8 (2)	N5—C17—C16	122.6 (3)
C5—C4—H4A	108.8	N5—C17—H17	118.7
S1—C4—H4A	108.8	C16—C17—H17	118.7
C5—C4—H4B	108.8	N5—C18—C19	122.3 (3)
S1—C4—H4B	108.8	N5—C18—H18	118.9
H4A—C4—H4B	107.7	C19—C18—H18	118.9
O1—C5—O2	121.7 (3)	C18—C19—C15	119.6 (3)
O1—C5—C4	121.3 (3)	C18—C19—H19	120.2
O2—C5—C4	116.9 (2)	C15—C19—H19	120.2
C7—C6—S2	115.7 (2)

Symmetry code: (i) −x+1, −y, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O4ⁱⁱ	0.82	1.64	2.460 (3)	175
O5—H5···N5ⁱⁱⁱ	0.82	1.74	2.554 (3)	174
C13—H13···O6^iv	0.93	2.47	3.335 (4)	156
C19—H19···O6^iv	0.93	2.34	3.245 (4)	164
C6—H6A···N1^v	0.97	2.58	3.533 (4)	168

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

Experimental details

Crystal data
Chemical formula	[Zn(C₉H₈N₃O₆S₃)₂(C₁₀H₈N₂)₂]
M_r	1078.47
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	8.6025 (7), 8.7606 (7), 15.3187 (12)
α, β, γ (°)	99.518 (1), 105.802 (2), 98.805 (1)
V (Å³)	1071.41 (15)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	0.94
Crystal size (mm)	0.28 × 0.24 × 0.23

Data collection
Diffractometer	Bruker SMART APEX CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.81, 0.84
No. of measured, independent and observed [I > 2σ(I)] reflections	5465, 3745, 3103
R_int	0.067
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.116, 1.05
No. of reflections	3745
No. of parameters	306
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.55, −0.63

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Zn1—O3	2.1145 (19)	Zn1—O1	2.189 (2)
Zn1—N4	2.135 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O4ⁱ	0.82	1.64	2.460 (3)	174.6
O5—H5···N5ⁱⁱ	0.82	1.74	2.554 (3)	173.8
C13—H13···O6ⁱⁱⁱ	0.93	2.47	3.335 (4)	155.6
C19—H19···O6ⁱⁱⁱ	0.93	2.34	3.245 (4)	164.0
C6—H6A···N1^iv	0.97	2.58	3.533 (4)	167.6

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

Acknowledgements

We acknowledge the National Natural Science Foundation of China (grant No. 20801025 and 20671048) for financial support.

References

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Volume 66| Part 4| April 2010| Pages m370-m371

doi:10.1107/S160053681000735X

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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Bis(4,4′-bipyrid­yl)bis­{2-[4,6-bis­­(carb­oxy­methyl­sulfan­yl)-1,3,5-triazin-2-ylsulfan­yl]acetato}zinc(II)

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

Bis(4,4′-bipyridyl)bis{2-[4,6-bis(carboxymethylsulfanyl)-1,3,5-triazin-2-ylsulfanyl]acetato}zinc(II)