(2,2'-Bipyridine-κN,N')(4-hydr-oxy-2-oxidobenzaldehyde thio-semicar-ba-zon-ato-κO,N,S)zinc(II).

The Zn(II) atom in the title compound, [Zn(C(8)H(7)N(3)O(2)S)(C(10)H(8)N(2))], is N,N'-chelated by the heterocycle and N,O,S-chelated by the doubly deprotonated Schiff base ligand in a distorted square-pyramidal environment. O-H⋯O and N-H⋯N hydrogen bonds link adjacent mol-ecules into a layer structure.

Related literature

For the square-pyramidal 1,10-phenanthroline adduct, which exists as a monohydrated n class="Chemical">DMSO disolvate, see: Tan et al. (2009 ▶).

Experimental

Crystal data

[Zn(C8n class="Species">H7N3O2S)(C10H8N2)]

M = 430.78

Monoclinic,

a = 16.1256 (4) Å

b = 7.0478 (2) Å

c = 17.6387 (5) Å

β = 113.646 (2)°

V = 1836.33 (9) Å3

Z = 4

Mo Kα radiation

μ = 1.48 mm−1

T = 100 (2) K

0.10 × 0.04 × 0.02 mm

Data collection

Bruker SMART APEX diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.867, T max = 0.971

15773 measured reflections

4191 independent reflections

2919 reflections with I > 2σ(I)

R int = 0.086

Refinement

R[F 2 > 2σ(F 2)] = 0.062

wR(F 2) = 0.195

S = 1.04

4191 reflections

245 parameters

24 restraints

H-atom parameters constrained

Δρmax = 0.88 e Å−3

Δρmin = −0.96 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2009 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808043973/tk2348sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808043973/tk2348Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Zn(C8H7N3O2S)(C10H8N2)]	F(000) = 880
Mr = 430.78	Dx = 1.558 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3053 reflections
a = 16.1256 (4) Å	θ = 2.3–26.2°
b = 7.0478 (2) Å	µ = 1.48 mm−1
c = 17.6387 (5) Å	T = 100 K
β = 113.646 (2)°	Prism, yellow
V = 1836.33 (9) Å3	0.10 × 0.04 × 0.02 mm
Z = 4

Bruker SMART APEX diffractometer	4191 independent reflections
Radiation source: fine-focus sealed tube	2919 reflections with I > 2σ(I)
graphite	Rint = 0.086
ω scans	θmax = 27.5°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −20→20
Tmin = 0.867, Tmax = 0.971	k = −9→9
15773 measured reflections	l = −21→22

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)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.195	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.1071P)2 + 3.3408P] where P = (Fo2 + 2Fc2)/3
4191 reflections	(Δ/σ)max = 0.001
245 parameters	Δρmax = 0.88 e Å−3
24 restraints	Δρmin = −0.96 e Å−3

	x	y	z	Uiso*/Ueq
Zn1	0.26010 (4)	0.61341 (9)	0.78222 (4)	0.0186 (2)
S1	0.35671 (10)	0.8297 (2)	0.75159 (9)	0.0239 (3)
O1	0.1393 (2)	0.4912 (5)	0.7423 (2)	0.0221 (8)
O2	−0.0804 (3)	−0.0017 (6)	0.6388 (2)	0.0238 (8)
H2	−0.0941	0.0325	0.6780	0.036*
N1	0.2953 (3)	0.4436 (7)	0.7058 (3)	0.0213 (10)
N2	0.3774 (3)	0.4754 (7)	0.6981 (3)	0.0226 (10)
N3	0.4867 (3)	0.6892 (7)	0.7112 (3)	0.0276 (11)
H31	0.5135	0.6021	0.6932	0.033*
H32	0.5107	0.8029	0.7242	0.033*
N4	0.3299 (3)	0.4781 (7)	0.8970 (3)	0.0276 (11)
N6	0.2340 (3)	0.7942 (6)	0.8656 (3)	0.0186 (9)
C1	0.1130 (4)	0.3300 (8)	0.7005 (3)	0.0198 (11)
C2	0.0305 (3)	0.2459 (8)	0.6918 (3)	0.0192 (11)
H2A	−0.0049	0.3053	0.7170	0.023*
C3	−0.0009 (4)	0.0790 (8)	0.6476 (3)	0.0199 (11)
C4	0.0493 (4)	−0.0115 (8)	0.6105 (3)	0.0250 (12)
H4	0.0276	−0.1248	0.5798	0.030*
C5	0.1305 (4)	0.0642 (8)	0.6187 (3)	0.0246 (12)
H5	0.1644	0.0017	0.5927	0.030*
C6	0.1660 (3)	0.2315 (7)	0.6641 (3)	0.0182 (10)
C7	0.2514 (4)	0.2930 (8)	0.6672 (3)	0.0210 (11)
H7	0.2788	0.2180	0.6388	0.025*
C8	0.4083 (4)	0.6481 (8)	0.7189 (3)	0.0233 (12)
C9	0.3807 (6)	0.3222 (11)	0.9082 (5)	0.0486 (19)
H9	0.3852	0.2632	0.8615	0.058*
C10	0.4268 (7)	0.2446 (14)	0.9857 (5)	0.068 (3)
H10	0.4631	0.1346	0.9924	0.082*
C11	0.4195 (6)	0.3282 (13)	1.0529 (5)	0.059 (2)
H11	0.4503	0.2752	1.1065	0.071*
C12	0.3680 (5)	0.4878 (11)	1.0429 (4)	0.0390 (16)
H12	0.3628	0.5480	1.0890	0.047*
C13	0.3235 (4)	0.5594 (9)	0.9635 (3)	0.0246 (12)
C14	0.2655 (4)	0.7348 (8)	0.9444 (3)	0.0235 (12)
C15	0.2450 (5)	0.8306 (10)	1.0037 (4)	0.0345 (15)
H15	0.2672	0.7861	1.0592	0.041*
C16	0.1917 (5)	0.9915 (11)	0.9804 (4)	0.0429 (18)
H16	0.1754	1.0573	1.0194	0.051*
C17	0.1624 (5)	1.0556 (9)	0.9000 (4)	0.0356 (15)
H17	0.1276	1.1684	0.8831	0.043*
C18	0.1848 (4)	0.9525 (8)	0.8448 (4)	0.0242 (12)
H18	0.1643	0.9961	0.7893	0.029*

	U11	U22	U33	U12	U13	U23
Zn1	0.0165 (3)	0.0207 (3)	0.0182 (3)	0.0020 (2)	0.0065 (2)	0.0029 (2)
S1	0.0208 (7)	0.0196 (7)	0.0340 (8)	0.0012 (5)	0.0139 (6)	0.0039 (5)
O1	0.0178 (19)	0.021 (2)	0.028 (2)	−0.0017 (15)	0.0101 (16)	−0.0024 (16)
O2	0.0186 (19)	0.027 (2)	0.025 (2)	−0.0039 (16)	0.0079 (16)	−0.0022 (16)
N1	0.018 (2)	0.026 (2)	0.021 (2)	−0.0014 (19)	0.0095 (19)	0.0022 (18)
N2	0.014 (2)	0.030 (3)	0.024 (2)	−0.0033 (19)	0.0094 (19)	−0.002 (2)
N3	0.022 (2)	0.025 (2)	0.043 (3)	−0.006 (2)	0.021 (2)	−0.005 (2)
N4	0.027 (3)	0.033 (3)	0.024 (2)	0.009 (2)	0.012 (2)	0.012 (2)
N6	0.016 (2)	0.019 (2)	0.019 (2)	0.0003 (17)	0.0052 (18)	0.0038 (17)
C1	0.020 (3)	0.019 (3)	0.019 (3)	0.002 (2)	0.007 (2)	0.004 (2)
C2	0.016 (2)	0.024 (3)	0.018 (2)	0.002 (2)	0.007 (2)	0.002 (2)
C3	0.015 (2)	0.023 (3)	0.018 (2)	0.001 (2)	0.002 (2)	0.006 (2)
C4	0.027 (3)	0.026 (3)	0.022 (3)	−0.002 (2)	0.010 (2)	0.000 (2)
C5	0.024 (3)	0.028 (3)	0.023 (3)	0.003 (2)	0.010 (2)	−0.003 (2)
C6	0.018 (3)	0.018 (3)	0.018 (2)	0.002 (2)	0.006 (2)	0.0031 (19)
C7	0.022 (3)	0.025 (3)	0.018 (3)	0.000 (2)	0.009 (2)	−0.001 (2)
C8	0.022 (3)	0.026 (3)	0.025 (3)	0.001 (2)	0.013 (2)	0.003 (2)
C9	0.059 (4)	0.049 (4)	0.048 (4)	0.032 (4)	0.032 (4)	0.022 (3)
C10	0.085 (6)	0.075 (5)	0.054 (5)	0.054 (5)	0.037 (4)	0.031 (4)
C11	0.065 (5)	0.076 (5)	0.039 (4)	0.037 (4)	0.024 (4)	0.032 (4)
C12	0.039 (4)	0.051 (4)	0.032 (3)	0.010 (3)	0.019 (3)	0.015 (3)
C13	0.020 (3)	0.031 (3)	0.021 (3)	0.000 (2)	0.006 (2)	0.007 (2)
C14	0.022 (3)	0.027 (3)	0.019 (3)	−0.007 (2)	0.005 (2)	−0.003 (2)
C15	0.042 (4)	0.036 (4)	0.021 (3)	0.001 (3)	0.008 (3)	−0.007 (2)
C16	0.053 (5)	0.041 (4)	0.029 (3)	0.004 (3)	0.011 (3)	−0.014 (3)
C17	0.040 (4)	0.028 (3)	0.034 (3)	0.010 (3)	0.010 (3)	−0.002 (3)
C18	0.020 (3)	0.023 (3)	0.023 (3)	−0.001 (2)	0.002 (2)	−0.001 (2)

Zn1—O1	1.983 (4)	C4—C5	1.367 (8)
Zn1—N1	2.045 (5)	C4—H4	0.9500
Zn1—N4	2.109 (5)	C5—C6	1.412 (8)
Zn1—N6	2.112 (5)	C5—H5	0.9500
Zn1—S1	2.3911 (15)	C6—C7	1.423 (7)
S1—C8	1.746 (6)	C7—H7	0.9500
O1—C1	1.329 (7)	C9—C10	1.381 (10)
O2—C3	1.354 (6)	C9—H9	0.9500
O2—H2	0.8400	C10—C11	1.370 (12)
N1—C7	1.306 (7)	C10—H10	0.9500
N1—N2	1.403 (6)	C11—C12	1.367 (10)
N2—C8	1.310 (7)	C11—H11	0.9500
N3—C8	1.355 (7)	C12—C13	1.387 (8)
N3—H31	0.8800	C12—H12	0.9500
N3—H32	0.8800	C13—C14	1.505 (8)
N4—C9	1.338 (8)	C14—C15	1.393 (8)
N4—C13	1.346 (8)	C15—C16	1.382 (10)
N6—C18	1.333 (7)	C15—H15	0.9500
N6—C14	1.340 (7)	C16—C17	1.380 (9)
C1—C2	1.408 (7)	C16—H16	0.9500
C1—C6	1.437 (7)	C17—C18	1.373 (9)
C2—C3	1.389 (8)	C17—H17	0.9500
C2—H2A	0.9500	C18—H18	0.9500
C3—C4	1.385 (8)
O1—Zn1—N1	90.29 (16)	C6—C5—H5	118.7
O1—Zn1—N4	102.37 (18)	C5—C6—C7	116.2 (5)
N1—Zn1—N4	100.70 (19)	C5—C6—C1	118.6 (5)
O1—Zn1—N6	93.82 (16)	C7—C6—C1	125.1 (5)
N1—Zn1—N6	175.77 (18)	N1—C7—C6	125.5 (5)
N4—Zn1—N6	77.46 (19)	N1—C7—H7	117.2
O1—Zn1—S1	146.42 (12)	C6—C7—H7	117.2
N1—Zn1—S1	81.14 (13)	N2—C8—N3	115.8 (5)
N4—Zn1—S1	111.10 (15)	N2—C8—S1	126.5 (4)
N6—Zn1—S1	95.92 (13)	N3—C8—S1	117.6 (4)
C8—S1—Zn1	92.73 (19)	N4—C9—C10	121.7 (7)
C1—O1—Zn1	128.1 (3)	N4—C9—H9	119.1
C3—O2—H2	109.5	C10—C9—H9	119.1
C7—N1—N2	114.5 (5)	C11—C10—C9	119.2 (7)
C7—N1—Zn1	125.7 (4)	C11—C10—H10	120.4
N2—N1—Zn1	119.5 (3)	C9—C10—H10	120.4
C8—N2—N1	112.9 (5)	C10—C11—C12	120.0 (7)
C8—N3—H31	120.0	C10—C11—H11	120.0
C8—N3—H32	120.0	C12—C11—H11	120.0
H31—N3—H32	120.0	C11—C12—C13	118.1 (7)
C9—N4—C13	118.5 (5)	C11—C12—H12	121.0
C9—N4—Zn1	124.9 (5)	C13—C12—H12	121.0
C13—N4—Zn1	116.5 (4)	N4—C13—C12	122.4 (6)
C18—N6—C14	118.9 (5)	N4—C13—C14	114.3 (5)
C18—N6—Zn1	125.2 (4)	C12—C13—C14	123.2 (6)
C14—N6—Zn1	115.8 (4)	N6—C14—C15	121.5 (6)
O1—C1—C2	119.8 (5)	N6—C14—C13	115.6 (5)
O1—C1—C6	123.2 (5)	C15—C14—C13	122.9 (5)
C2—C1—C6	117.0 (5)	C16—C15—C14	118.7 (6)
C3—C2—C1	122.2 (5)	C16—C15—H15	120.6
C3—C2—H2A	118.9	C14—C15—H15	120.6
C1—C2—H2A	118.9	C17—C16—C15	119.3 (6)
O2—C3—C4	117.3 (5)	C17—C16—H16	120.3
O2—C3—C2	122.4 (5)	C15—C16—H16	120.3
C4—C3—C2	120.3 (5)	C18—C17—C16	118.5 (6)
C5—C4—C3	119.2 (5)	C18—C17—H17	120.8
C5—C4—H4	120.4	C16—C17—H17	120.8
C3—C4—H4	120.4	N6—C18—C17	123.0 (5)
C4—C5—C6	122.6 (5)	N6—C18—H18	118.5
C4—C5—H5	118.7	C17—C18—H18	118.5
O1—Zn1—S1—C8	−95.8 (3)	C4—C5—C6—C1	−2.5 (8)
N1—Zn1—S1—C8	−18.8 (2)	O1—C1—C6—C5	−178.1 (5)
N4—Zn1—S1—C8	79.3 (2)	C2—C1—C6—C5	3.3 (7)
N6—Zn1—S1—C8	158.1 (2)	O1—C1—C6—C7	−0.7 (8)
N1—Zn1—O1—C1	15.3 (4)	C2—C1—C6—C7	−179.2 (5)
N4—Zn1—O1—C1	−85.8 (4)	N2—N1—C7—C6	−178.8 (5)
N6—Zn1—O1—C1	−163.8 (4)	Zn1—N1—C7—C6	7.3 (8)
S1—Zn1—O1—C1	89.5 (5)	C5—C6—C7—N1	180.0 (5)
O1—Zn1—N1—C7	−13.1 (5)	C1—C6—C7—N1	2.5 (9)
N4—Zn1—N1—C7	89.5 (5)	N1—N2—C8—N3	−178.7 (5)
S1—Zn1—N1—C7	−160.5 (5)	N1—N2—C8—S1	−1.0 (7)
O1—Zn1—N1—N2	173.2 (4)	Zn1—S1—C8—N2	17.3 (5)
N4—Zn1—N1—N2	−84.1 (4)	Zn1—S1—C8—N3	−165.0 (4)
S1—Zn1—N1—N2	25.8 (4)	C13—N4—C9—C10	−0.5 (12)
C7—N1—N2—C8	163.9 (5)	Zn1—N4—C9—C10	178.0 (7)
Zn1—N1—N2—C8	−21.8 (6)	N4—C9—C10—C11	0.7 (15)
O1—Zn1—N4—C9	92.1 (6)	C9—C10—C11—C12	−0.8 (16)
N1—Zn1—N4—C9	−0.5 (6)	C10—C11—C12—C13	0.6 (13)
N6—Zn1—N4—C9	−176.7 (6)	C9—N4—C13—C12	0.3 (10)
S1—Zn1—N4—C9	−85.1 (6)	Zn1—N4—C13—C12	−178.3 (5)
O1—Zn1—N4—C13	−89.4 (4)	C9—N4—C13—C14	179.5 (6)
N1—Zn1—N4—C13	177.9 (4)	Zn1—N4—C13—C14	0.9 (6)
N6—Zn1—N4—C13	1.8 (4)	C11—C12—C13—N4	−0.4 (10)
S1—Zn1—N4—C13	93.4 (4)	C11—C12—C13—C14	−179.5 (7)
O1—Zn1—N6—C18	−78.4 (4)	C18—N6—C14—C15	2.6 (8)
N4—Zn1—N6—C18	179.8 (5)	Zn1—N6—C14—C15	−173.4 (5)
S1—Zn1—N6—C18	69.4 (4)	C18—N6—C14—C13	−177.6 (5)
O1—Zn1—N6—C14	97.3 (4)	Zn1—N6—C14—C13	6.4 (6)
N4—Zn1—N6—C14	−4.6 (4)	N4—C13—C14—N6	−4.9 (7)
S1—Zn1—N6—C14	−114.9 (4)	C12—C13—C14—N6	174.3 (6)
Zn1—O1—C1—C2	167.2 (4)	N4—C13—C14—C15	174.9 (6)
Zn1—O1—C1—C6	−11.3 (7)	C12—C13—C14—C15	−5.9 (9)
O1—C1—C2—C3	179.0 (5)	N6—C14—C15—C16	−0.7 (10)
C6—C1—C2—C3	−2.4 (8)	C13—C14—C15—C16	179.5 (6)
C1—C2—C3—O2	−179.6 (5)	C14—C15—C16—C17	−1.7 (11)
C1—C2—C3—C4	0.3 (8)	C15—C16—C17—C18	2.3 (11)
O2—C3—C4—C5	−179.3 (5)	C14—N6—C18—C17	−2.0 (9)
C2—C3—C4—C5	0.7 (8)	Zn1—N6—C18—C17	173.5 (5)
C3—C4—C5—C6	0.4 (9)	C16—C17—C18—N6	−0.5 (10)
C4—C5—C6—C7	179.9 (5)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1i	0.84	1.85	2.625 (5)	153
N3—H32···N2ii	0.88	2.15	2.936 (7)	148

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O1i	0.84	1.85	2.625 (5)	153
N3—H32⋯N2ii	0.88	2.15	2.936 (7)	148

Symmetry codes: (i) ; (ii) .