catena-Poly[[(1,10-phenanthroline-κ2N,N′)zinc]-μ-4-sulfonato­benzo­triazolido-κ3N3,O:N1]

Cheng, X.-C.

doi:10.1107/S160053681104743X

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 12| December 2011| Page m1758

https://doi.org/10.1107/S160053681104743X

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catena-Poly[[(1,10-phenanthroline-κ²N,N′)zinc]-μ-4-sulfonatobenzotriazolido-κ³N³,O:N¹]

Xiao-Chun Cheng ^a ^*

^aFaculty of Life Science and Chemical Engineering, Huaiyin Institute of Technology, Huaian 223003, People's Republic of China
^*Correspondence e-mail: shxycheng@163.com

(Received 7 November 2011; accepted 9 November 2011; online 12 November 2011)

In the title complex, [Zn(C₆H₃N₃O₃S)(C₁₂H₈N₂)]_n, the Zn²⁺ cation is coordinated by two N atoms from two 4-sulfonatobenzotriazolide dianions, two N atoms from a 1,10-phenanthroline molecule and a sulfonate O atom from a 4-sulfonatobenzotriazolide anion, displaying a distorted ZnN₄O trigonal–bipyramidal geometry. Each 1,10-phenanthroline ligand displays a bidentate chelating coordinating mode and the 4-sulfonatobenzotriazolide ions act as μ₂-bridges, linking different Zn²⁺ cations into a chain along the b axis. The crystal structure is consolidated by C—H⋯O hydrogen-bonding interactions.

Related literature

For related structures, see: Xia et al. (2010 ).

Experimental

Crystal data

[Zn(C₆H₃N₃O₃S)(C₁₂H₈N₂)]
M_r = 442.75
Orthorhombic, P c c n
a = 14.5562 (19) Å
b = 25.903 (3) Å
c = 8.9239 (12) Å
V = 3364.8 (8) Å³
Z = 8
Mo Kα radiation
μ = 1.62 mm⁻¹
T = 293 K
0.20 × 0.20 × 0.20 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.738, T_max = 0.738
19596 measured reflections
3819 independent reflections
2895 reflections with I > 2σ(I)
R_int = 0.092

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.147
S = 1.10
3819 reflections
253 parameters
H-atom parameters constrained
Δρ_max = 0.82 e Å⁻³
Δρ_min = −0.70 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9⋯O2ⁱ	0.93	2.49	3.351 (5)	154
C12—H12⋯O2ⁱⁱ	0.93	2.55	3.369 (5)	148
Symmetry codes: (i) -x+2, -y+1, -z; (ii) $[-x+{\script{3\over 2}}, y, z-{\script{1\over 2}}]$ .

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: DIAMOND (Brandenburg, 2000 ); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S160053681104743X/pv2482sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681104743X/pv2482Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S160053681104743X/pv2482Isup3.cdx

checkCIF report

Comment top

Benzotriazole-4-sulfonic acid is often used as a ligand to synthesize complexes for its variable coordination modes. Herein, we report the crystal structure of the title complex. The asymmetric unit consists of one zinc ion, one 1,10-phenanthroline molecule, and one 4-sulfonatobenzotriazolide anion. each Zn ion is coordinated by two N atoms from two different 4-sulfonatobenzotriazolide anions, two N atoms from one 1,10-phenanthroline molecule, and one sulfonate O atoms from one 4-sulfonatobenzotriazolide anions, displaying a distorted ZnN₄O trigonal bipyramidal geometry (Fig. 1). Each 1,10-phenanthroline displays a bidentate coordinating mode. And every 4-sulfonatobenzotriazolide acts as a µ₂-bridge, linking different zinc ions to form a one-dimensional chain along the b axis direction. The crystal structure is consolidated by hydrogen bonding interactions of the type C—H···O (Table 1).

Related literature top

For related structures, see: Xia et al. (2010).

Experimental top

A mixture of zinc nitrate hexahydrate (59.4 mg, 0.2 mmol), benzotriazole-4-sulfonic acid (39.8 mg, 0.2 mmol), 1,10-phenanthroline (36.0 mg, 0.2 mmol) and potassium hydroxide (22.4 mg, 0.4 mmol) in 12 ml H₂O was sealed in a 16 ml Teflon-lined stainless steel container and heated to 413 K for 3 days. After cooling the container to the room temperature, colorless block crystals of the title complex were obtained.

Structure description top

For related structures, see: Xia et al. (2010).

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: DIAMOND (Brandenburg, 2000); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. : The coordination environment of zinc ion in the title complex with the ellipsoids drawn at the 30% probability level. The hydrogen atoms are omitted for clarity. Symmetry codes: A = x, -y + 1/2, z + 1/2; B = x, -y + 1/2, z - 1/2.

catena-Poly[[(1,10-phenanthroline-κ²N,N')zinc]-µ- 4-sulfonatobenzotriazolido-κ³N³,O:N¹] top

Crystal data top

[Zn(C₆H₃N₃O₃S)(C₁₂H₈N₂)]	F(000) = 1792
M_r = 442.75	D_x = 1.748 Mg m⁻³
Orthorhombic, Pccn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ab 2ac	Cell parameters from 2885 reflections
a = 14.5562 (19) Å	θ = 2.7–25.0°
b = 25.903 (3) Å	µ = 1.62 mm⁻¹
c = 8.9239 (12) Å	T = 293 K
V = 3364.8 (8) Å³	Block, colorless
Z = 8	0.20 × 0.20 × 0.20 mm

Data collection top

Bruker SMART APEXII CCD diffractometer	3819 independent reflections
Radiation source: fine-focus sealed tube	2895 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.092
φ and ω scans	θ_max = 27.4°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −18→18
T_min = 0.738, T_max = 0.738	k = −33→33
19596 measured reflections	l = −7→11

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.147	H-atom parameters constrained
S = 1.10	w = 1/[σ²(F_o²) + (0.0628P)² + 1.2933P] where P = (F_o² + 2F_c²)/3
3819 reflections	(Δ/σ)_max = 0.001
253 parameters	Δρ_max = 0.82 e Å⁻³
0 restraints	Δρ_min = −0.70 e Å⁻³

Crystal data top

[Zn(C₆H₃N₃O₃S)(C₁₂H₈N₂)]	V = 3364.8 (8) Å³
M_r = 442.75	Z = 8
Orthorhombic, Pccn	Mo Kα radiation
a = 14.5562 (19) Å	µ = 1.62 mm⁻¹
b = 25.903 (3) Å	T = 293 K
c = 8.9239 (12) Å	0.20 × 0.20 × 0.20 mm

Data collection top

Bruker SMART APEXII CCD diffractometer	3819 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2895 reflections with I > 2σ(I)
T_min = 0.738, T_max = 0.738	R_int = 0.092
19596 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.147	H-atom parameters constrained
S = 1.10	Δρ_max = 0.82 e Å⁻³
3819 reflections	Δρ_min = −0.70 e Å⁻³
253 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	0.97927 (3)	0.330127 (13)	0.19495 (5)	0.02895 (17)
N5	0.8384 (2)	0.34450 (11)	0.1826 (3)	0.0334 (7)
C17	0.8148 (2)	0.38273 (12)	0.0857 (4)	0.0333 (8)
C9	0.9411 (4)	0.47031 (16)	−0.1724 (5)	0.0581 (13)
H9	0.9313	0.4973	−0.2392	0.070*
C10	0.8673 (3)	0.44934 (14)	−0.0912 (5)	0.0454 (10)
C13	0.7232 (3)	0.39803 (14)	0.0600 (5)	0.0421 (9)
C14	0.6559 (3)	0.36901 (16)	0.1331 (5)	0.0497 (11)
H14	0.5942	0.3767	0.1170	0.060*
C7	1.0419 (3)	0.41028 (15)	−0.0526 (5)	0.0459 (10)
H7	1.1012	0.3977	−0.0398	0.055*
C18	0.8878 (3)	0.40801 (12)	0.0054 (4)	0.0337 (8)
C16	0.7712 (3)	0.31927 (15)	0.2529 (5)	0.0420 (9)
H16	0.7865	0.2937	0.3216	0.050*
C15	0.6784 (3)	0.32995 (16)	0.2270 (6)	0.0508 (12)
H15	0.6328	0.3105	0.2735	0.061*
N4	0.9732 (2)	0.38901 (11)	0.0256 (4)	0.0356 (7)
S1	1.10686 (6)	0.40039 (3)	0.37277 (12)	0.0366 (2)
N1	0.99027 (19)	0.29840 (10)	0.4183 (3)	0.0279 (6)
N2	0.9579 (2)	0.25262 (10)	0.4630 (3)	0.0312 (6)
C1	1.1157 (2)	0.35655 (11)	0.5213 (4)	0.0293 (7)
C2	1.1777 (3)	0.35925 (14)	0.6343 (5)	0.0392 (9)
H2	1.2171	0.3875	0.6391	0.047*
C3	1.1841 (3)	0.32053 (16)	0.7447 (5)	0.0441 (10)
H3	1.2267	0.3242	0.8217	0.053*
O1	1.10445 (18)	0.36563 (10)	0.2416 (3)	0.0391 (6)
O3	1.1878 (2)	0.43226 (10)	0.3728 (4)	0.0511 (8)
O2	1.0199 (2)	0.42648 (11)	0.3896 (4)	0.0628 (10)
N3	1.0018 (2)	0.23706 (11)	0.5874 (3)	0.0307 (6)
C6	1.0567 (2)	0.31302 (11)	0.5174 (4)	0.0257 (7)
C5	1.0640 (2)	0.27433 (12)	0.6254 (4)	0.0294 (7)
C4	1.1290 (3)	0.27760 (15)	0.7414 (4)	0.0375 (8)
H4	1.1344	0.2517	0.8130	0.045*
C12	0.7058 (3)	0.44058 (16)	−0.0377 (6)	0.0551 (12)
H12	0.6456	0.4514	−0.0526	0.066*
C11	0.7738 (3)	0.46542 (16)	−0.1083 (6)	0.0581 (13)
H11	0.7602	0.4935	−0.1692	0.070*
C8	1.0273 (3)	0.45068 (18)	−0.1525 (6)	0.0553 (12)
H8	1.0764	0.4644	−0.2059	0.066*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.0395 (3)	0.0203 (2)	0.0271 (3)	0.00316 (14)	−0.00219 (17)	−0.00023 (15)
N5	0.0423 (17)	0.0270 (14)	0.0309 (17)	−0.0015 (12)	−0.0001 (13)	−0.0032 (12)
C17	0.0427 (19)	0.0239 (16)	0.033 (2)	0.0031 (13)	−0.0079 (16)	−0.0106 (14)
C9	0.100 (4)	0.032 (2)	0.043 (3)	−0.005 (2)	−0.005 (3)	0.0132 (18)
C10	0.074 (3)	0.0236 (17)	0.038 (2)	0.0022 (17)	−0.016 (2)	0.0010 (16)
C13	0.045 (2)	0.041 (2)	0.041 (2)	0.0082 (17)	−0.0131 (19)	−0.0133 (17)
C14	0.041 (2)	0.052 (2)	0.055 (3)	0.0053 (18)	−0.006 (2)	−0.022 (2)
C7	0.054 (2)	0.036 (2)	0.048 (3)	−0.0056 (17)	0.007 (2)	0.0085 (18)
C18	0.048 (2)	0.0231 (16)	0.0296 (19)	0.0012 (14)	−0.0052 (16)	−0.0027 (14)
C16	0.051 (2)	0.0347 (19)	0.041 (2)	−0.0063 (17)	0.007 (2)	−0.0041 (17)
C15	0.046 (2)	0.047 (3)	0.059 (3)	−0.0087 (18)	0.008 (2)	−0.018 (2)
N4	0.0468 (18)	0.0287 (15)	0.0312 (17)	0.0009 (12)	−0.0005 (14)	0.0031 (13)
S1	0.0427 (5)	0.0234 (4)	0.0437 (6)	−0.0010 (3)	0.0040 (4)	0.0088 (4)
N1	0.0386 (15)	0.0217 (13)	0.0232 (14)	0.0007 (11)	−0.0012 (12)	0.0012 (11)
N2	0.0422 (16)	0.0241 (14)	0.0273 (15)	−0.0041 (11)	−0.0026 (13)	0.0017 (12)
C1	0.0381 (18)	0.0188 (15)	0.0311 (18)	−0.0014 (12)	0.0053 (15)	−0.0012 (13)
C2	0.045 (2)	0.0339 (19)	0.038 (2)	−0.0103 (15)	−0.0016 (18)	−0.0019 (16)
C3	0.045 (2)	0.051 (2)	0.036 (2)	−0.0136 (18)	−0.016 (2)	0.0041 (19)
O1	0.0430 (14)	0.0394 (15)	0.0350 (14)	−0.0068 (11)	0.0000 (12)	0.0070 (12)
O3	0.0644 (18)	0.0334 (14)	0.0557 (19)	−0.0201 (13)	0.0057 (15)	0.0051 (13)
O2	0.060 (2)	0.0438 (17)	0.084 (3)	0.0201 (14)	0.0185 (17)	0.0227 (17)
N3	0.0406 (16)	0.0248 (14)	0.0267 (16)	−0.0011 (11)	−0.0032 (13)	0.0029 (12)
C6	0.0327 (17)	0.0222 (14)	0.0221 (16)	−0.0027 (12)	0.0009 (14)	−0.0006 (12)
C5	0.0370 (18)	0.0223 (15)	0.0288 (18)	−0.0012 (13)	−0.0008 (15)	0.0001 (13)
C4	0.042 (2)	0.038 (2)	0.032 (2)	−0.0055 (15)	−0.0067 (17)	0.0088 (16)
C12	0.059 (3)	0.051 (3)	0.056 (3)	0.021 (2)	−0.025 (2)	−0.011 (2)
C11	0.078 (3)	0.035 (2)	0.061 (3)	0.015 (2)	−0.028 (3)	0.006 (2)
C8	0.073 (3)	0.046 (2)	0.048 (3)	−0.014 (2)	0.006 (2)	0.010 (2)

Geometric parameters (Å, º) top

Zn1—N3ⁱ	2.014 (3)	C15—H15	0.9300
Zn1—O1	2.083 (3)	S1—O3	1.439 (3)
Zn1—N5	2.086 (3)	S1—O2	1.443 (3)
Zn1—N4	2.149 (3)	S1—O1	1.477 (3)
Zn1—N1	2.162 (3)	S1—C1	1.750 (4)
N5—C16	1.334 (5)	N1—N2	1.337 (4)
N5—C17	1.359 (5)	N1—C6	1.364 (4)
C17—C13	1.410 (5)	N2—N3	1.343 (4)
C17—C18	1.440 (5)	C1—C2	1.355 (5)
C9—C8	1.365 (7)	C1—C6	1.418 (4)
C9—C10	1.405 (7)	C2—C3	1.409 (6)
C9—H9	0.9300	C2—H2	0.9300
C10—C18	1.407 (5)	C3—C4	1.372 (5)
C10—C11	1.431 (6)	C3—H3	0.9300
C13—C14	1.397 (6)	N3—C5	1.366 (4)
C13—C12	1.427 (6)	N3—Zn1ⁱⁱ	2.014 (3)
C14—C15	1.354 (7)	C6—C5	1.395 (4)
C14—H14	0.9300	C5—C4	1.405 (5)
C7—N4	1.338 (5)	C4—H4	0.9300
C7—C8	1.391 (6)	C12—C11	1.338 (7)
C7—H7	0.9300	C12—H12	0.9300
C18—N4	1.349 (5)	C11—H11	0.9300
C16—C15	1.398 (6)	C8—H8	0.9300
C16—H16	0.9300

N3ⁱ—Zn1—O1	109.52 (12)	C18—N4—Zn1	113.0 (2)
N3ⁱ—Zn1—N5	106.80 (12)	O3—S1—O2	116.73 (18)
O1—Zn1—N5	142.30 (11)	O3—S1—O1	111.69 (17)
N3ⁱ—Zn1—N4	106.53 (12)	O2—S1—O1	110.3 (2)
O1—Zn1—N4	82.14 (11)	O3—S1—C1	108.17 (18)
N5—Zn1—N4	78.21 (11)	O2—S1—C1	106.83 (18)
N3ⁱ—Zn1—N1	95.67 (11)	O1—S1—C1	101.91 (15)
O1—Zn1—N1	85.34 (11)	N2—N1—C6	107.6 (3)
N5—Zn1—N1	100.92 (11)	N2—N1—Zn1	125.9 (2)
N4—Zn1—N1	157.12 (11)	C6—N1—Zn1	123.0 (2)
C16—N5—C17	118.1 (3)	N1—N2—N3	110.2 (3)
C16—N5—Zn1	127.5 (3)	C2—C1—C6	117.6 (3)
C17—N5—Zn1	114.4 (2)	C2—C1—S1	125.4 (3)
N5—C17—C13	123.2 (4)	C6—C1—S1	116.9 (3)
N5—C17—C18	117.5 (3)	C1—C2—C3	121.9 (3)
C13—C17—C18	119.3 (3)	C1—C2—H2	119.1
C8—C9—C10	119.4 (4)	C3—C2—H2	119.1
C8—C9—H9	120.3	C4—C3—C2	121.5 (4)
C10—C9—H9	120.3	C4—C3—H3	119.2
C9—C10—C18	116.6 (4)	C2—C3—H3	119.2
C9—C10—C11	124.0 (4)	S1—O1—Zn1	116.64 (16)
C18—C10—C11	119.3 (4)	N2—N3—C5	108.0 (3)
C14—C13—C17	115.8 (4)	N2—N3—Zn1ⁱⁱ	125.1 (2)
C14—C13—C12	125.3 (4)	C5—N3—Zn1ⁱⁱ	126.9 (2)
C17—C13—C12	118.9 (4)	N1—C6—C5	107.6 (3)
C15—C14—C13	121.4 (4)	N1—C6—C1	131.8 (3)
C15—C14—H14	119.3	C5—C6—C1	120.5 (3)
C13—C14—H14	119.3	N3—C5—C6	106.6 (3)
N4—C7—C8	122.0 (4)	N3—C5—C4	132.2 (3)
N4—C7—H7	119.0	C6—C5—C4	121.1 (3)
C8—C7—H7	119.0	C3—C4—C5	117.3 (3)
N4—C18—C10	123.7 (4)	C3—C4—H4	121.3
N4—C18—C17	116.6 (3)	C5—C4—H4	121.3
C10—C18—C17	119.6 (3)	C11—C12—C13	121.9 (4)
N5—C16—C15	122.3 (4)	C11—C12—H12	119.1
N5—C16—H16	118.9	C13—C12—H12	119.1
C15—C16—H16	118.9	C12—C11—C10	120.9 (4)
C14—C15—C16	119.0 (4)	C12—C11—H11	119.6
C14—C15—H15	120.5	C10—C11—H11	119.6
C16—C15—H15	120.5	C9—C8—C7	120.3 (4)
C7—N4—C18	117.9 (3)	C9—C8—H8	119.9
C7—N4—Zn1	128.9 (3)	C7—C8—H8	119.9

N3ⁱ—Zn1—N5—C16	70.4 (3)	N3ⁱ—Zn1—N1—C6	117.1 (3)
O1—Zn1—N5—C16	−125.6 (3)	O1—Zn1—N1—C6	7.9 (3)
N4—Zn1—N5—C16	174.3 (3)	N5—Zn1—N1—C6	−134.6 (3)
N1—Zn1—N5—C16	−29.0 (3)	N4—Zn1—N1—C6	−49.0 (4)
N3ⁱ—Zn1—N5—C17	−106.6 (2)	C6—N1—N2—N3	−0.4 (4)
O1—Zn1—N5—C17	57.5 (3)	Zn1—N1—N2—N3	158.8 (2)
N4—Zn1—N5—C17	−2.6 (2)	O3—S1—C1—C2	12.6 (4)
N1—Zn1—N5—C17	154.0 (2)	O2—S1—C1—C2	−113.8 (4)
C16—N5—C17—C13	2.1 (5)	O1—S1—C1—C2	130.4 (3)
Zn1—N5—C17—C13	179.4 (3)	O3—S1—C1—C6	−163.3 (3)
C16—N5—C17—C18	−177.2 (3)	O2—S1—C1—C6	70.3 (3)
Zn1—N5—C17—C18	0.0 (4)	O1—S1—C1—C6	−45.5 (3)
C8—C9—C10—C18	−1.1 (6)	C6—C1—C2—C3	0.0 (6)
C8—C9—C10—C11	−177.1 (4)	S1—C1—C2—C3	−175.9 (3)
N5—C17—C13—C14	−4.2 (5)	C1—C2—C3—C4	1.3 (7)
C18—C17—C13—C14	175.2 (3)	O3—S1—O1—Zn1	−165.49 (16)
N5—C17—C13—C12	176.5 (3)	O2—S1—O1—Zn1	−33.9 (2)
C18—C17—C13—C12	−4.2 (5)	C1—S1—O1—Zn1	79.25 (19)
C17—C13—C14—C15	2.3 (6)	N3ⁱ—Zn1—O1—S1	−152.98 (16)
C12—C13—C14—C15	−178.3 (4)	N5—Zn1—O1—S1	43.2 (3)
C9—C10—C18—N4	1.6 (6)	N4—Zn1—O1—S1	102.19 (18)
C11—C10—C18—N4	177.9 (4)	N1—Zn1—O1—S1	−58.61 (17)
C9—C10—C18—C17	−176.5 (3)	N1—N2—N3—C5	0.7 (4)
C11—C10—C18—C17	−0.2 (5)	N1—N2—N3—Zn1ⁱⁱ	−178.7 (2)
N5—C17—C18—N4	4.5 (5)	N2—N1—C6—C5	0.0 (4)
C13—C17—C18—N4	−174.8 (3)	Zn1—N1—C6—C5	−160.0 (2)
N5—C17—C18—C10	−177.2 (3)	N2—N1—C6—C1	177.1 (3)
C13—C17—C18—C10	3.4 (5)	Zn1—N1—C6—C1	17.1 (5)
C17—N5—C16—C15	1.8 (6)	C2—C1—C6—N1	−177.8 (4)
Zn1—N5—C16—C15	−175.0 (3)	S1—C1—C6—N1	−1.6 (5)
C13—C14—C15—C16	1.2 (7)	C2—C1—C6—C5	−1.0 (5)
N5—C16—C15—C14	−3.5 (7)	S1—C1—C6—C5	175.3 (3)
C8—C7—N4—C18	−0.2 (6)	N2—N3—C5—C6	−0.7 (4)
C8—C7—N4—Zn1	−175.8 (3)	Zn1ⁱⁱ—N3—C5—C6	178.7 (2)
C10—C18—N4—C7	−1.0 (5)	N2—N3—C5—C4	−178.1 (4)
C17—C18—N4—C7	177.2 (3)	Zn1ⁱⁱ—N3—C5—C4	1.3 (6)
C10—C18—N4—Zn1	175.3 (3)	N1—C6—C5—N3	0.5 (4)
C17—C18—N4—Zn1	−6.6 (4)	C1—C6—C5—N3	−177.1 (3)
N3ⁱ—Zn1—N4—C7	−75.0 (3)	N1—C6—C5—C4	178.2 (3)
O1—Zn1—N4—C7	33.1 (3)	C1—C6—C5—C4	0.6 (5)
N5—Zn1—N4—C7	−179.2 (4)	C2—C3—C4—C5	−1.6 (6)
N1—Zn1—N4—C7	90.6 (4)	N3—C5—C4—C3	177.7 (4)
N3ⁱ—Zn1—N4—C18	109.2 (3)	C6—C5—C4—C3	0.7 (6)
O1—Zn1—N4—C18	−142.6 (3)	C14—C13—C12—C11	−177.5 (4)
N5—Zn1—N4—C18	5.0 (2)	C17—C13—C12—C11	1.8 (6)
N1—Zn1—N4—C18	−85.2 (4)	C13—C12—C11—C10	1.5 (7)
N3ⁱ—Zn1—N1—N2	−39.2 (3)	C9—C10—C11—C12	173.7 (5)
O1—Zn1—N1—N2	−148.4 (3)	C18—C10—C11—C12	−2.3 (6)
N5—Zn1—N1—N2	69.1 (3)	C10—C9—C8—C7	0.0 (7)
N4—Zn1—N1—N2	154.7 (3)	N4—C7—C8—C9	0.7 (7)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···O2ⁱⁱⁱ	0.93	2.49	3.351 (5)	154
C12—H12···O2^iv	0.93	2.55	3.369 (5)	148

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

Experimental details

Crystal data
Chemical formula	[Zn(C₆H₃N₃O₃S)(C₁₂H₈N₂)]
M_r	442.75
Crystal system, space group	Orthorhombic, Pccn
Temperature (K)	293
a, b, c (Å)	14.5562 (19), 25.903 (3), 8.9239 (12)
V (Å³)	3364.8 (8)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	1.62
Crystal size (mm)	0.20 × 0.20 × 0.20

Data collection
Diffractometer	Bruker SMART APEXII CCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.738, 0.738
No. of measured, independent and observed [I > 2σ(I)] reflections	19596, 3819, 2895
R_int	0.092
(sin θ/λ)_max (Å⁻¹)	0.648

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.147, 1.10
No. of reflections	3819
No. of parameters	253
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.82, −0.70

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 2000), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···O2ⁱ	0.93	2.49	3.351 (5)	154
C12—H12···O2ⁱⁱ	0.93	2.55	3.369 (5)	148

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

References

Brandenburg, K. (2000). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. 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
Xia, M.-Z., Lei, W., Wang, F.-Y., Jin, Z.-W. & Yang, T.-H. (2010). Asian J. Chem. 22, 3741–3744. CAS Google Scholar

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