Bis(acetone 4-phenyl-thio-semi-carbazonato-κN,S)zinc(II).

The Zn(II) atom in the title compound, [Zn(C(10)H(12)N(3)S)(2)], is N,S-chelated by the deprotonated Schiff base in a tetra-hedral environment. The metal atom lies on a twofold rotation axis that relates one anion to the other. The amino H atom forms an intermolecular N-H⋯π inter-action to an aromatic ring.

Related literature

For the two modifications of acetone 4-phenyl­thio­semicarbazone, see: Jian et al. (2005 ▶); Venkatraman et al. (2005 ▶).

Experimental

Crystal data

[Zn(C10H12N3S)2]

M = 477.94

Monoclinic,

a = 23.5203 (5) Å

b = 7.2938 (2) Å

c = 15.1134 (5) Å

β = 122.761 (2)°

V = 2180.3 (1) Å3

Z = 4

Mo Kα radiation

μ = 1.34 mm−1

T = 153 K

0.30 × 0.20 × 0.05 mm

Data collection

Bruker SMART APEX diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.690, T max = 0.936

6983 measured reflections

2488 independent reflections

1896 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.103

S = 1.10

2488 reflections

135 parameters

H-atom parameters constrained

Δρmax = 0.40 e Å−3

Δρmin = −0.45 e Å−3

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: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2009 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809028244/bt5011sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809028244/bt5011Isup2.hkl

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

[Zn(C10H12N3S)2]	F(000) = 992
Mr = 477.94	Dx = 1.456 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2390 reflections
a = 23.5203 (5) Å	θ = 3.8–28.0°
b = 7.2938 (2) Å	µ = 1.34 mm−1
c = 15.1134 (5) Å	T = 153 K
β = 122.761 (2)°	Wedge, brown
V = 2180.3 (1) Å3	0.30 × 0.20 × 0.05 mm
Z = 4

Bruker SMART APEX diffractometer	2488 independent reflections
Radiation source: fine-focus sealed tube	1896 reflections with I > 2σ(I)
graphite	Rint = 0.031
ω scans	θmax = 27.5°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −30→30
Tmin = 0.690, Tmax = 0.936	k = −9→9
6983 measured reflections	l = −19→19

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.103	H-atom parameters constrained
S = 1.10	w = 1/[σ2(Fo2) + (0.0387P)2 + 4.48P] where P = (Fo2 + 2Fc2)/3
2488 reflections	(Δ/σ)max = 0.001
135 parameters	Δρmax = 0.40 e Å−3
0 restraints	Δρmin = −0.45 e Å−3

	x	y	z	Uiso*/Ueq
Zn1	0.5000	0.30141 (7)	0.2500	0.03064 (17)
S1	0.55393 (4)	0.14771 (13)	0.18550 (8)	0.0501 (3)
N1	0.58756 (10)	0.4440 (3)	0.34189 (19)	0.0245 (5)
N2	0.64335 (10)	0.3888 (3)	0.33788 (19)	0.0253 (5)
N3	0.68276 (11)	0.1943 (4)	0.2634 (2)	0.0336 (6)
H3	0.6712	0.1130	0.2154	0.040*
C1	0.75216 (12)	0.2404 (4)	0.3216 (2)	0.0255 (6)
C2	0.78857 (13)	0.1872 (4)	0.2775 (2)	0.0296 (6)
H2	0.7662	0.1268	0.2113	0.035*
C3	0.85719 (14)	0.2225 (4)	0.3300 (3)	0.0348 (7)
H3A	0.8816	0.1866	0.2993	0.042*
C4	0.89046 (13)	0.3090 (4)	0.4263 (3)	0.0332 (7)
H4	0.9376	0.3330	0.4620	0.040*
C5	0.85427 (13)	0.3606 (4)	0.4703 (2)	0.0289 (6)
H5	0.8770	0.4194	0.5370	0.035*
C6	0.78518 (13)	0.3275 (4)	0.4181 (2)	0.0283 (6)
H6	0.7608	0.3646	0.4486	0.034*
C7	0.63093 (13)	0.2588 (4)	0.2715 (2)	0.0275 (6)
C8	0.59964 (13)	0.5716 (4)	0.4081 (2)	0.0302 (7)
C9	0.66790 (15)	0.6551 (5)	0.4773 (3)	0.0456 (9)
H9A	0.7007	0.5590	0.5196	0.068*
H9B	0.6663	0.7453	0.5241	0.068*
H9C	0.6815	0.7159	0.4338	0.068*
C10	0.54313 (16)	0.6384 (5)	0.4182 (3)	0.0451 (9)
H10A	0.5039	0.5575	0.3784	0.068*
H10B	0.5307	0.7633	0.3903	0.068*
H10C	0.5578	0.6380	0.4925	0.068*

	U11	U22	U33	U12	U13	U23
Zn1	0.0144 (2)	0.0296 (3)	0.0436 (3)	0.000	0.0129 (2)	0.000
S1	0.0171 (3)	0.0539 (6)	0.0665 (7)	−0.0064 (3)	0.0143 (4)	−0.0345 (5)
N1	0.0156 (9)	0.0257 (12)	0.0320 (14)	0.0020 (9)	0.0128 (10)	0.0034 (11)
N2	0.0148 (10)	0.0287 (12)	0.0321 (14)	0.0015 (9)	0.0124 (10)	−0.0009 (11)
N3	0.0196 (11)	0.0373 (14)	0.0408 (16)	−0.0017 (10)	0.0143 (11)	−0.0158 (13)
C1	0.0168 (11)	0.0235 (14)	0.0328 (16)	0.0030 (10)	0.0113 (12)	0.0006 (12)
C2	0.0245 (13)	0.0303 (15)	0.0332 (17)	0.0041 (12)	0.0152 (13)	−0.0016 (14)
C3	0.0241 (14)	0.0429 (18)	0.0432 (19)	0.0065 (13)	0.0221 (14)	0.0041 (16)
C4	0.0189 (12)	0.0373 (17)	0.0398 (18)	0.0023 (12)	0.0136 (13)	0.0086 (15)
C5	0.0216 (13)	0.0264 (14)	0.0310 (17)	0.0007 (11)	0.0092 (12)	0.0040 (13)
C6	0.0219 (13)	0.0307 (16)	0.0328 (17)	0.0034 (11)	0.0152 (13)	0.0004 (13)
C7	0.0171 (12)	0.0299 (15)	0.0328 (17)	−0.0001 (11)	0.0116 (12)	−0.0030 (13)
C8	0.0228 (13)	0.0258 (15)	0.0408 (18)	0.0015 (11)	0.0165 (13)	−0.0037 (14)
C9	0.0297 (15)	0.0361 (19)	0.063 (2)	−0.0023 (13)	0.0197 (17)	−0.0213 (17)
C10	0.0321 (16)	0.046 (2)	0.062 (2)	0.0046 (14)	0.0284 (17)	−0.0102 (18)

Zn1—N1	2.039 (2)	C3—C4	1.376 (5)
Zn1—N1i	2.039 (2)	C3—H3A	0.9500
Zn1—S1	2.2702 (8)	C4—C5	1.386 (4)
Zn1—S1i	2.2702 (8)	C4—H4	0.9500
S1—C7	1.754 (3)	C5—C6	1.390 (4)
N1—C8	1.281 (4)	C5—H5	0.9500
N1—N2	1.405 (3)	C6—H6	0.9500
N2—C7	1.294 (4)	C8—C9	1.492 (4)
N3—C7	1.372 (3)	C8—C10	1.499 (4)
N3—C1	1.413 (3)	C9—H9A	0.9800
N3—H3	0.8600	C9—H9B	0.9800
C1—C6	1.381 (4)	C9—H9C	0.9800
C1—C2	1.395 (4)	C10—H10A	0.9800
C2—C3	1.384 (4)	C10—H10B	0.9800
C2—H2	0.9500	C10—H10C	0.9800
N1—Zn1—N1i	118.66 (13)	C5—C4—H4	120.5
N1—Zn1—S1	87.20 (6)	C4—C5—C6	120.9 (3)
N1i—Zn1—S1	123.54 (7)	C4—C5—H5	119.6
N1—Zn1—S1i	123.54 (7)	C6—C5—H5	119.6
N1i—Zn1—S1i	87.20 (6)	C1—C6—C5	119.7 (3)
S1—Zn1—S1i	120.82 (6)	C1—C6—H6	120.1
C7—S1—Zn1	92.67 (9)	C5—C6—H6	120.1
C8—N1—N2	115.1 (2)	N2—C7—N3	118.8 (2)
C8—N1—Zn1	128.17 (17)	N2—C7—S1	128.47 (19)
N2—N1—Zn1	116.57 (17)	N3—C7—S1	112.8 (2)
C7—N2—N1	114.8 (2)	N1—C8—C9	123.0 (2)
C7—N3—C1	130.2 (3)	N1—C8—C10	118.8 (3)
C7—N3—H3	114.9	C9—C8—C10	118.2 (3)
C1—N3—H3	114.9	C8—C9—H9A	109.5
C6—C1—C2	119.5 (2)	C8—C9—H9B	109.5
C6—C1—N3	124.5 (2)	H9A—C9—H9B	109.5
C2—C1—N3	116.0 (3)	C8—C9—H9C	109.5
C3—C2—C1	120.1 (3)	H9A—C9—H9C	109.5
C3—C2—H2	120.0	H9B—C9—H9C	109.5
C1—C2—H2	120.0	C8—C10—H10A	109.5
C4—C3—C2	120.8 (3)	C8—C10—H10B	109.5
C4—C3—H3A	119.6	H10A—C10—H10B	109.5
C2—C3—H3A	119.6	C8—C10—H10C	109.5
C3—C4—C5	119.1 (2)	H10A—C10—H10C	109.5
C3—C4—H4	120.5	H10B—C10—H10C	109.5
N1—Zn1—S1—C7	4.02 (12)	C2—C3—C4—C5	0.0 (5)
N1i—Zn1—S1—C7	126.96 (13)	C3—C4—C5—C6	−0.6 (4)
S1i—Zn1—S1—C7	−123.93 (11)	C2—C1—C6—C5	−0.3 (4)
N1i—Zn1—N1—C8	52.6 (2)	N3—C1—C6—C5	177.8 (3)
S1—Zn1—N1—C8	179.7 (3)	C4—C5—C6—C1	0.7 (4)
S1i—Zn1—N1—C8	−54.6 (3)	N1—N2—C7—N3	−179.0 (2)
N1i—Zn1—N1—N2	−132.0 (2)	N1—N2—C7—S1	1.3 (4)
S1—Zn1—N1—N2	−4.85 (18)	C1—N3—C7—N2	3.8 (5)
S1i—Zn1—N1—N2	120.81 (17)	C1—N3—C7—S1	−176.5 (3)
C8—N1—N2—C7	179.4 (3)	Zn1—S1—C7—N2	−4.3 (3)
Zn1—N1—N2—C7	3.4 (3)	Zn1—S1—C7—N3	176.0 (2)
C7—N3—C1—C6	18.0 (5)	N2—N1—C8—C9	−0.7 (4)
C7—N3—C1—C2	−163.9 (3)	Zn1—N1—C8—C9	174.8 (2)
C6—C1—C2—C3	−0.3 (4)	N2—N1—C8—C10	−179.7 (3)
N3—C1—C2—C3	−178.5 (3)	Zn1—N1—C8—C10	−4.1 (4)
C1—C2—C3—C4	0.4 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···Cgii	0.86	2.86	3.671 (3)	157

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3⋯Cgi	0.86	2.86	3.671 (3)	157

Symmetry code: (i) . Cg is the centroid of the aromatic ring.